data_rv137 #?# MeasurementCode _publ_contact_author_name 'H. Mayr' _publ_contact_author_address ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; loop_ _publ_author_name _publ_author_address 'Elsa Follet' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Guillaume Berionni' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Peter Mayer' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus F) D-81377 M\"unchen Bundesrepublik Deutschland ; 'Herbert Mayr' ; Department Chemie Ludwig-Maximilians Universit\"at Butenandtstra\&se 5-13 (Haus D) D-81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_email 'Herbert.Mayr@cup.uni-muenchen.de' _publ_contact_author_fax '+49 89 2180 77717' _publ_contact_author_phone ? _publ_requested_journal 'Chem. Eur. J.' _publ_section_title ; Structure and Reactivity of Indolyl Methylium Ions: Scope and Limitations in Synthetic Applications ; _publ_section_abstract ? _publ_section_comment ? _audit_update_record 22-Apr-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour orange _exptl_crystal_size_max 0.156 #?# in millimeters _exptl_crystal_size_mid 0.115 #?# in millimeters _exptl_crystal_size_min 0.087 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Peter Mayer' #?# X-ray operator _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 123(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation '0.8_mm' _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? _cell_length_a 6.0708(3) _cell_length_b 16.5232(10) _cell_length_c 15.1156(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.019(2) _cell_angle_gamma 90.00 _cell_volume 1510.42(15) _cell_measurement_temperature 123(2) #?# in K _cell_measurement_reflns_used 117 _cell_measurement_theta_min 3.9422 _cell_measurement_theta_max 20.9994 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8849 _exptl_absorpt_correction_T_max 0.9281 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 34989 #xl _diffrn_reflns_av_R_equivalents 0.0464 #xl _diffrn_reflns_av_sigmaI/netI 0.0244 #xl _diffrn_reflns_limit_h_min -7 #xl _diffrn_reflns_limit_h_max 7 #xl _diffrn_reflns_limit_k_min -20 #xl _diffrn_reflns_limit_k_max 20 #xl _diffrn_reflns_limit_l_min -18 #xl _diffrn_reflns_limit_l_max 18 #xl _diffrn_reflns_theta_min 2.81 #xl _diffrn_reflns_theta_max 26.45 #xl _diffrn_measured_fraction_theta_max 0.997 #xl _diffrn_reflns_theta_full 26.39 #xl _diffrn_measured_fraction_theta_full 0.997 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3085 #xl _reflns_number_gt 2143 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+1.1687P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 3085 #xl _refine_ls_number_parameters 210 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0775 #xl _refine_ls_R_factor_gt 0.0470 #xl _refine_ls_wR_factor_ref 0.1229 #xl _refine_ls_wR_factor_gt 0.1068 #xl _refine_ls_goodness_of_fit_ref 1.017 #xl _refine_ls_restrained_S_all 1.017 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.341 #xl _refine_diff_density_min -0.419 #xl _refine_diff_density_rms 0.042 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1897(3) 0.33074(11) 0.53075(10) 0.0368(4) Uani 1 1 d . . . C1 C 0.0598(4) 0.39291(14) 0.48150(15) 0.0458(6) Uani 1 1 d . . . H1A H 0.1356 0.4451 0.4891 0.069 Uiso 1 1 calc R . . H1B H -0.0864 0.3967 0.5040 0.069 Uiso 1 1 calc R . . H1C H 0.0430 0.3786 0.4183 0.069 Uiso 1 1 calc R . . C2 C 0.3797(3) 0.34235(14) 0.57714(12) 0.0371(5) Uani 1 1 d . . . H2 H 0.4539 0.3929 0.5840 0.045 Uiso 1 1 calc R . . C3 C 0.4591(3) 0.26765(13) 0.61598(12) 0.0353(5) Uani 1 1 d . . . C4 C 0.2633(4) 0.12636(15) 0.60370(13) 0.0427(5) Uani 1 1 d . . . H4 H 0.3727 0.0970 0.6393 0.051 Uiso 1 1 calc R . . C5 C 0.0721(4) 0.08885(15) 0.56751(14) 0.0465(6) Uani 1 1 d . . . H5 H 0.0506 0.0330 0.5788 0.056 Uiso 1 1 calc R . . C6 C -0.0893(4) 0.13098(15) 0.51495(14) 0.0446(6) Uani 1 1 d . . . H6 H -0.2180 0.1032 0.4910 0.054 Uiso 1 1 calc R . . C7 C -0.0660(3) 0.21228(15) 0.49702(13) 0.0398(5) Uani 1 1 d . . . H7 H -0.1750 0.2416 0.4612 0.048 Uiso 1 1 calc R . . C8 C 0.1255(3) 0.24867(14) 0.53427(12) 0.0355(5) Uani 1 1 d . . . C9 C 0.2902(3) 0.20813(14) 0.58639(12) 0.0355(5) Uani 1 1 d . . . C10 C 0.6455(3) 0.25092(14) 0.67008(12) 0.0361(5) Uani 1 1 d . . . H10 H 0.6621 0.1951 0.6842 0.043 Uiso 1 1 calc R . . C11 C 0.8221(3) 0.30042(13) 0.71015(12) 0.0343(5) Uani 1 1 d . . . C12 C 0.8318(3) 0.38517(14) 0.70709(13) 0.0386(5) Uani 1 1 d . . . H12 H 0.7156 0.4146 0.6755 0.046 Uiso 1 1 calc R . . C13 C 1.0082(3) 0.42595(14) 0.74939(14) 0.0395(5) Uani 1 1 d . . . H13 H 1.0122 0.4834 0.7464 0.047 Uiso 1 1 calc R . . C14 C 1.1813(3) 0.38488(14) 0.79658(12) 0.0362(5) Uani 1 1 d . . . C15 C 1.3696(4) 0.42941(15) 0.84538(15) 0.0479(6) Uani 1 1 d . . . H15A H 1.3380 0.4376 0.9072 0.072 Uiso 1 1 calc R . . H15B H 1.3883 0.4820 0.8171 0.072 Uiso 1 1 calc R . . H15C H 1.5056 0.3977 0.8438 0.072 Uiso 1 1 calc R . . C16 C 1.1736(3) 0.30100(14) 0.79902(12) 0.0372(5) Uani 1 1 d . . . H16 H 1.2915 0.2719 0.8299 0.045 Uiso 1 1 calc R . . C17 C 0.9976(3) 0.25933(14) 0.75726(12) 0.0353(5) Uani 1 1 d . . . H17 H 0.9949 0.2019 0.7604 0.042 Uiso 1 1 calc R . . F1 F 0.5511(2) 0.33469(9) 0.39721(9) 0.0580(4) Uani 1 1 d . . . F2 F 0.5716(3) 0.46907(10) 0.41311(11) 0.0805(6) Uani 1 1 d . . . F3 F 0.3283(2) 0.41569(9) 0.30800(9) 0.0561(4) Uani 1 1 d . . . F4 F 0.6936(2) 0.40943(8) 0.29269(9) 0.0536(4) Uani 1 1 d . . . B1 B 0.5358(4) 0.40761(15) 0.35231(15) 0.0348(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0262(8) 0.0557(12) 0.0279(9) -0.0018(8) -0.0010(7) 0.0046(8) C1 0.0350(12) 0.0595(15) 0.0408(12) 0.0043(11) -0.0075(9) 0.0045(10) C2 0.0262(10) 0.0565(14) 0.0282(10) -0.0067(9) -0.0002(8) 0.0034(9) C3 0.0263(10) 0.0549(13) 0.0247(9) -0.0080(9) 0.0018(8) 0.0072(9) C4 0.0399(12) 0.0578(15) 0.0292(11) -0.0052(10) -0.0032(9) 0.0065(10) C5 0.0479(13) 0.0560(15) 0.0343(12) -0.0043(10) -0.0028(10) -0.0008(11) C6 0.0357(12) 0.0655(16) 0.0319(11) -0.0061(11) -0.0007(9) -0.0060(11) C7 0.0286(10) 0.0662(16) 0.0240(10) -0.0021(10) -0.0003(8) 0.0021(10) C8 0.0293(10) 0.0559(14) 0.0216(9) -0.0041(9) 0.0035(8) 0.0033(9) C9 0.0285(10) 0.0565(14) 0.0215(9) -0.0089(9) 0.0019(8) 0.0062(9) C10 0.0302(10) 0.0522(13) 0.0260(10) -0.0063(9) 0.0030(8) 0.0080(9) C11 0.0252(10) 0.0539(13) 0.0237(9) -0.0060(9) 0.0018(8) 0.0074(9) C12 0.0308(11) 0.0527(14) 0.0308(11) -0.0036(9) -0.0048(9) 0.0108(9) C13 0.0340(11) 0.0512(14) 0.0322(10) -0.0022(10) -0.0028(9) 0.0054(10) C14 0.0276(10) 0.0561(14) 0.0251(10) 0.0002(9) 0.0031(8) 0.0018(9) C15 0.0356(12) 0.0654(16) 0.0411(12) 0.0059(11) -0.0067(10) -0.0024(11) C16 0.0251(10) 0.0610(15) 0.0251(10) 0.0034(9) 0.0003(8) 0.0078(9) C17 0.0289(10) 0.0505(13) 0.0266(10) -0.0011(9) 0.0031(8) 0.0062(9) F1 0.0454(8) 0.0684(10) 0.0576(8) 0.0271(7) -0.0102(6) -0.0126(7) F2 0.0772(11) 0.0754(11) 0.0827(11) -0.0464(9) -0.0282(9) 0.0236(9) F3 0.0360(7) 0.0846(10) 0.0452(8) 0.0031(7) -0.0115(6) 0.0081(7) F4 0.0456(8) 0.0651(9) 0.0513(8) 0.0134(7) 0.0117(6) 0.0003(6) B1 0.0302(12) 0.0402(13) 0.0329(12) -0.0033(10) -0.0045(9) 0.0025(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.311(3) . ? N1 C8 1.413(3) . ? N1 C1 1.459(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.432(3) . ? C2 H2 0.9500 . ? C3 C10 1.365(3) . ? C3 C9 1.462(3) . ? C4 C5 1.386(3) . ? C4 C9 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 C9 1.390(3) . ? C10 C11 1.439(3) . ? C10 H10 0.9500 . ? C11 C12 1.402(3) . ? C11 C17 1.404(3) . ? C12 C13 1.375(3) . ? C12 H12 0.9500 . ? C13 C14 1.394(3) . ? C13 H13 0.9500 . ? C14 C16 1.387(3) . ? C14 C15 1.498(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.377(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? F1 B1 1.382(3) . ? F2 B1 1.374(3) . ? F3 B1 1.380(3) . ? F4 B1 1.372(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C8 110.68(18) . . ? C2 N1 C1 125.52(19) . . ? C8 N1 C1 123.80(17) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.0(2) . . ? N1 C2 H2 125.0 . . ? C3 C2 H2 125.0 . . ? C10 C3 C2 130.7(2) . . ? C10 C3 C9 124.7(2) . . ? C2 C3 C9 104.63(17) . . ? C5 C4 C9 118.0(2) . . ? C5 C4 H4 121.0 . . ? C9 C4 H4 121.0 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 116.1(2) . . ? C6 C7 H7 121.9 . . ? C8 C7 H7 121.9 . . ? C7 C8 C9 123.9(2) . . ? C7 C8 N1 128.77(19) . . ? C9 C8 N1 107.25(17) . . ? C4 C9 C8 119.03(19) . . ? C4 C9 C3 133.44(19) . . ? C8 C9 C3 107.44(19) . . ? C3 C10 C11 133.2(2) . . ? C3 C10 H10 113.4 . . ? C11 C10 H10 113.4 . . ? C12 C11 C17 117.88(19) . . ? C12 C11 C10 125.83(18) . . ? C17 C11 C10 116.3(2) . . ? C13 C12 C11 120.48(19) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 121.4(2) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C16 C14 C13 118.34(19) . . ? C16 C14 C15 120.22(19) . . ? C13 C14 C15 121.4(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C14 120.90(19) . . ? C17 C16 H16 119.5 . . ? C14 C16 H16 119.5 . . ? C16 C17 C11 121.0(2) . . ? C16 C17 H17 119.5 . . ? C11 C17 H17 119.5 . . ? F4 B1 F2 110.14(19) . . ? F4 B1 F3 109.84(18) . . ? F2 B1 F3 109.70(18) . . ? F4 B1 F1 108.71(18) . . ? F2 B1 F1 108.42(19) . . ? F3 B1 F1 110.00(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C2 C3 0.0(2) . . . . ? C1 N1 C2 C3 -179.75(18) . . . . ? N1 C2 C3 C10 -178.79(19) . . . . ? N1 C2 C3 C9 0.2(2) . . . . ? C9 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C6 C7 C8 N1 -177.01(19) . . . . ? C2 N1 C8 C7 177.64(19) . . . . ? C1 N1 C8 C7 -2.6(3) . . . . ? C2 N1 C8 C9 -0.3(2) . . . . ? C1 N1 C8 C9 179.50(17) . . . . ? C5 C4 C9 C8 0.2(3) . . . . ? C5 C4 C9 C3 176.2(2) . . . . ? C7 C8 C9 C4 -0.7(3) . . . . ? N1 C8 C9 C4 177.37(17) . . . . ? C7 C8 C9 C3 -177.64(17) . . . . ? N1 C8 C9 C3 0.4(2) . . . . ? C10 C3 C9 C4 2.4(3) . . . . ? C2 C3 C9 C4 -176.7(2) . . . . ? C10 C3 C9 C8 178.70(18) . . . . ? C2 C3 C9 C8 -0.4(2) . . . . ? C2 C3 C10 C11 2.9(4) . . . . ? C9 C3 C10 C11 -175.92(19) . . . . ? C3 C10 C11 C12 5.7(3) . . . . ? C3 C10 C11 C17 -175.2(2) . . . . ? C17 C11 C12 C13 -0.2(3) . . . . ? C10 C11 C12 C13 178.89(19) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C16 0.9(3) . . . . ? C12 C13 C14 C15 -177.8(2) . . . . ? C13 C14 C16 C17 -1.2(3) . . . . ? C15 C14 C16 C17 177.57(18) . . . . ? C14 C16 C17 C11 0.8(3) . . . . ? C12 C11 C17 C16 -0.1(3) . . . . ? C10 C11 C17 C16 -179.23(17) . . . . ? _audit_block_code C17H16N_BF4_rv137_mayr _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C17 H16 N, B F4' _chemical_formula_sum 'C17 H16 B F4 N' _chemical_formula_weight 321.120 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.41216(14) _exptl_crystal_F_000 664 data_rv390 #?# MeasurementCode _audit_update_record 23-Oct-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour red _exptl_crystal_size_max 0.151 #?# in millimeters _exptl_crystal_size_mid 0.145 #?# in millimeters _exptl_crystal_size_min 0.126 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Peter Mayer' #?# X-ray operator _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 100(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation '0.8_mm' _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? _cell_length_a 12.5113(8) _cell_length_b 7.8864(5) _cell_length_c 16.1050(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.1986(17) _cell_angle_gamma 90.00 _cell_volume 1553.19(17) _cell_measurement_temperature 100(2) #?# in K _cell_measurement_reflns_used 129 _cell_measurement_theta_min 2.9295 _cell_measurement_theta_max 33.4710 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 26880 #xl _diffrn_reflns_av_R_equivalents 0.0444 #xl _diffrn_reflns_av_sigmaI/netI 0.0227 #xl _diffrn_reflns_limit_h_min -15 #xl _diffrn_reflns_limit_h_max 15 #xl _diffrn_reflns_limit_k_min -9 #xl _diffrn_reflns_limit_k_max 9 #xl _diffrn_reflns_limit_l_min -19 #xl _diffrn_reflns_limit_l_max 19 #xl _diffrn_reflns_theta_min 3.20 #xl _diffrn_reflns_theta_max 25.46 #xl _diffrn_measured_fraction_theta_max 0.990 #xl _diffrn_reflns_theta_full 25.38 #xl _diffrn_measured_fraction_theta_full 0.990 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 2824 #xl _reflns_number_gt 2329 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+2.2179P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2824 #xl _refine_ls_number_parameters 219 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0650 #xl _refine_ls_R_factor_gt 0.0512 #xl _refine_ls_wR_factor_ref 0.1193 #xl _refine_ls_wR_factor_gt 0.1119 #xl _refine_ls_goodness_of_fit_ref 1.036 #xl _refine_ls_restrained_S_all 1.036 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.484 #xl _refine_diff_density_min -0.634 #xl _refine_diff_density_rms 0.050 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13608(18) 0.5803(3) 0.34010(14) 0.0280(5) Uani 1 1 d . . . H1A H 0.1611 0.5461 0.2889 0.042 Uiso 1 1 calc R . . H1B H 0.1337 0.7044 0.3430 0.042 Uiso 1 1 calc R . . H1C H 0.0628 0.5344 0.3381 0.042 Uiso 1 1 calc R . . C2 C 0.30165(16) 0.4280(3) 0.41530(13) 0.0197(5) Uani 1 1 d . . . H2 H 0.3268 0.3957 0.3659 0.024 Uiso 1 1 calc R . . C3 C 0.35594(17) 0.3893(3) 0.50053(13) 0.0193(5) Uani 1 1 d . . . C4 C 0.29518(19) 0.4776(3) 0.64073(14) 0.0254(5) Uani 1 1 d . . . H4 H 0.3545 0.4271 0.6794 0.030 Uiso 1 1 calc R . . C6 C 0.12543(19) 0.6376(3) 0.61344(15) 0.0290(5) Uani 1 1 d . . . H6 H 0.0709 0.6959 0.6353 0.035 Uiso 1 1 calc R . . C5 C 0.21367(19) 0.5646(3) 0.66948(15) 0.0292(5) Uani 1 1 d . . . H5 H 0.2181 0.5747 0.7289 0.035 Uiso 1 1 calc R . . C9 C 0.28736(17) 0.4667(3) 0.55347(14) 0.0204(5) Uani 1 1 d . . . C8 C 0.19847(17) 0.5411(3) 0.49901(14) 0.0205(5) Uani 1 1 d . . . C7 C 0.11599(18) 0.6266(3) 0.52646(15) 0.0250(5) Uani 1 1 d . . . H7 H 0.0560 0.6752 0.4877 0.030 Uiso 1 1 calc R . . C10 C 0.45105(17) 0.3021(3) 0.53111(13) 0.0199(5) Uani 1 1 d . . . H10 H 0.4712 0.2994 0.5914 0.024 Uiso 1 1 calc R . . C11 C 0.52580(16) 0.2146(3) 0.49028(13) 0.0192(5) Uani 1 1 d . . . C12 C 0.50981(18) 0.1861(3) 0.40220(14) 0.0241(5) Uani 1 1 d . . . H12 H 0.4449 0.2256 0.3655 0.029 Uiso 1 1 calc R . . C13 C 0.58679(18) 0.1022(3) 0.36895(14) 0.0248(5) Uani 1 1 d . . . H13 H 0.5749 0.0837 0.3094 0.030 Uiso 1 1 calc R . . C14 C 0.68293(17) 0.0432(3) 0.42193(14) 0.0202(5) Uani 1 1 d . . . C15 C 0.85657(18) -0.0919(3) 0.43075(15) 0.0274(5) Uani 1 1 d . . . H15A H 0.8956 0.0054 0.4607 0.041 Uiso 1 1 calc R . . H15B H 0.9000 -0.1412 0.3928 0.041 Uiso 1 1 calc R . . H15C H 0.8449 -0.1773 0.4721 0.041 Uiso 1 1 calc R . . C16 C 0.70021(17) 0.0660(3) 0.50953(13) 0.0201(5) Uani 1 1 d . . . H16 H 0.7648 0.0247 0.5460 0.024 Uiso 1 1 calc R . . C17 C 0.62151(17) 0.1498(3) 0.54219(13) 0.0190(4) Uani 1 1 d . . . H17 H 0.6324 0.1641 0.6020 0.023 Uiso 1 1 calc R . . B1 B 0.3980(2) 0.6124(4) 0.21451(16) 0.0274(6) Uani 1 1 d . . . N1 N 0.21162(14) 0.5150(2) 0.41515(11) 0.0206(4) Uani 1 1 d . . . O1 O 0.75292(12) -0.0370(2) 0.38188(10) 0.0271(4) Uani 1 1 d . . . F1 F 0.42001(14) 0.4605(2) 0.25628(12) 0.0536(5) Uani 1 1 d . . . F2 F 0.46462(16) 0.7359(2) 0.25921(10) 0.0558(5) Uani 1 1 d . . . F3 F 0.41865(15) 0.6045(3) 0.13486(9) 0.0721(7) Uani 1 1 d . . . F4 F 0.28993(15) 0.6500(3) 0.20785(15) 0.0831(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0244(12) 0.0314(13) 0.0275(12) 0.0045(10) 0.0039(10) 0.0022(10) C2 0.0205(11) 0.0169(10) 0.0235(11) -0.0024(9) 0.0088(9) -0.0028(9) C3 0.0192(10) 0.0160(10) 0.0239(11) -0.0005(9) 0.0073(9) -0.0044(9) C4 0.0276(12) 0.0249(12) 0.0246(12) -0.0002(10) 0.0076(9) -0.0034(10) C6 0.0275(12) 0.0251(12) 0.0403(14) -0.0033(10) 0.0208(11) -0.0033(10) C5 0.0336(13) 0.0310(13) 0.0275(12) -0.0035(10) 0.0166(10) -0.0050(11) C9 0.0195(10) 0.0165(10) 0.0266(11) -0.0012(9) 0.0083(9) -0.0039(9) C8 0.0203(11) 0.0167(10) 0.0261(11) -0.0009(9) 0.0088(9) -0.0049(9) C7 0.0198(11) 0.0203(11) 0.0370(13) 0.0004(10) 0.0106(10) -0.0012(9) C10 0.0219(11) 0.0162(10) 0.0225(11) -0.0011(9) 0.0065(9) -0.0057(9) C11 0.0195(11) 0.0153(10) 0.0228(11) 0.0003(9) 0.0045(9) -0.0027(8) C12 0.0219(11) 0.0253(12) 0.0233(11) -0.0004(10) 0.0006(9) 0.0050(9) C13 0.0258(12) 0.0294(12) 0.0183(10) -0.0034(10) 0.0030(9) 0.0044(10) C14 0.0189(10) 0.0159(10) 0.0264(11) -0.0018(9) 0.0059(9) 0.0002(9) C15 0.0199(11) 0.0303(13) 0.0314(12) -0.0015(10) 0.0043(9) 0.0065(10) C16 0.0173(10) 0.0166(10) 0.0250(11) 0.0006(9) 0.0012(9) -0.0023(9) C17 0.0217(11) 0.0170(10) 0.0186(10) -0.0010(8) 0.0045(8) -0.0043(8) B1 0.0271(13) 0.0340(15) 0.0217(13) 0.0050(11) 0.0062(11) -0.0009(12) N1 0.0202(9) 0.0197(9) 0.0224(9) 0.0012(8) 0.0059(7) -0.0016(8) O1 0.0225(8) 0.0328(9) 0.0258(8) -0.0037(7) 0.0048(7) 0.0090(7) F1 0.0546(10) 0.0333(9) 0.0729(12) 0.0141(8) 0.0130(9) 0.0014(8) F2 0.0889(13) 0.0381(9) 0.0360(9) -0.0076(7) 0.0034(8) -0.0124(9) F3 0.0610(11) 0.1343(19) 0.0236(8) -0.0166(10) 0.0149(8) -0.0580(12) F4 0.0410(10) 0.1070(17) 0.1108(17) 0.0587(14) 0.0378(11) 0.0289(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.462(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.319(3) . ? C2 C3 1.430(3) . ? C2 H2 0.9500 . ? C3 C10 1.373(3) . ? C3 C9 1.464(3) . ? C4 C5 1.387(3) . ? C4 C9 1.391(3) . ? C4 H4 0.9500 . ? C6 C7 1.383(3) . ? C6 C5 1.394(3) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C9 C8 1.392(3) . ? C8 C7 1.381(3) . ? C8 N1 1.410(3) . ? C7 H7 0.9500 . ? C10 C11 1.430(3) . ? C10 H10 0.9500 . ? C11 C17 1.404(3) . ? C11 C12 1.408(3) . ? C12 C13 1.368(3) . ? C12 H12 0.9500 . ? C13 C14 1.399(3) . ? C13 H13 0.9500 . ? C14 O1 1.350(3) . ? C14 C16 1.393(3) . ? C15 O1 1.434(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? B1 F3 1.362(3) . ? B1 F4 1.366(3) . ? B1 F1 1.373(3) . ? B1 F2 1.382(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.19(18) . . ? N1 C2 H2 124.9 . . ? C3 C2 H2 124.9 . . ? C10 C3 C2 130.64(19) . . ? C10 C3 C9 124.76(19) . . ? C2 C3 C9 104.60(18) . . ? C5 C4 C9 117.9(2) . . ? C5 C4 H4 121.0 . . ? C9 C4 H4 121.0 . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C4 C9 C8 119.1(2) . . ? C4 C9 C3 133.6(2) . . ? C8 C9 C3 107.29(18) . . ? C7 C8 C9 123.8(2) . . ? C7 C8 N1 128.6(2) . . ? C9 C8 N1 107.61(18) . . ? C8 C7 C6 116.4(2) . . ? C8 C7 H7 121.8 . . ? C6 C7 H7 121.8 . . ? C3 C10 C11 132.8(2) . . ? C3 C10 H10 113.6 . . ? C11 C10 H10 113.6 . . ? C17 C11 C12 117.62(19) . . ? C17 C11 C10 117.42(19) . . ? C12 C11 C10 124.96(19) . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? O1 C14 C16 124.54(19) . . ? O1 C14 C13 115.16(18) . . ? C16 C14 C13 120.29(19) . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C14 118.52(19) . . ? C17 C16 H16 120.7 . . ? C14 C16 H16 120.7 . . ? C16 C17 C11 122.36(19) . . ? C16 C17 H17 118.8 . . ? C11 C17 H17 118.8 . . ? F3 B1 F4 108.5(2) . . ? F3 B1 F1 111.3(2) . . ? F4 B1 F1 108.7(2) . . ? F3 B1 F2 108.0(2) . . ? F4 B1 F2 111.5(2) . . ? F1 B1 F2 108.9(2) . . ? C2 N1 C8 110.28(18) . . ? C2 N1 C1 126.01(18) . . ? C8 N1 C1 123.70(18) . . ? C14 O1 C15 118.80(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C10 179.9(2) . . . . ? N1 C2 C3 C9 -0.7(2) . . . . ? C9 C4 C5 C6 0.8(3) . . . . ? C7 C6 C5 C4 -0.3(4) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? C5 C4 C9 C3 179.3(2) . . . . ? C10 C3 C9 C4 0.6(4) . . . . ? C2 C3 C9 C4 -178.8(2) . . . . ? C10 C3 C9 C8 -179.4(2) . . . . ? C2 C3 C9 C8 1.2(2) . . . . ? C4 C9 C8 C7 0.0(3) . . . . ? C3 C9 C8 C7 180.0(2) . . . . ? C4 C9 C8 N1 178.74(19) . . . . ? C3 C9 C8 N1 -1.2(2) . . . . ? C9 C8 C7 C6 0.6(3) . . . . ? N1 C8 C7 C6 -177.9(2) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C2 C3 C10 C11 -3.1(4) . . . . ? C9 C3 C10 C11 177.6(2) . . . . ? C3 C10 C11 C17 174.9(2) . . . . ? C3 C10 C11 C12 -6.2(4) . . . . ? C17 C11 C12 C13 -1.7(3) . . . . ? C10 C11 C12 C13 179.3(2) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 O1 -179.7(2) . . . . ? C12 C13 C14 C16 1.5(3) . . . . ? O1 C14 C16 C17 -179.7(2) . . . . ? C13 C14 C16 C17 -1.0(3) . . . . ? C14 C16 C17 C11 -0.9(3) . . . . ? C12 C11 C17 C16 2.3(3) . . . . ? C10 C11 C17 C16 -178.75(19) . . . . ? C3 C2 N1 C8 -0.1(2) . . . . ? C3 C2 N1 C1 178.56(19) . . . . ? C7 C8 N1 C2 179.5(2) . . . . ? C9 C8 N1 C2 0.8(2) . . . . ? C7 C8 N1 C1 0.9(3) . . . . ? C9 C8 N1 C1 -177.83(19) . . . . ? C16 C14 O1 C15 -5.2(3) . . . . ? C13 C14 O1 C15 176.1(2) . . . . ? _audit_block_code C17H16NO_BF4_rv390_mayr _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C17 H16 N O, B F4' _chemical_formula_sum 'C17 H16 B F4 N O' _chemical_formula_weight 337.120 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.44170(16) _exptl_crystal_F_000 696 data_rv253 #?# MeasurementCode _audit_update_record 12-Jul-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour red _exptl_crystal_size_max 0.147 #?# in millimeters _exptl_crystal_size_mid 0.125 #?# in millimeters _exptl_crystal_size_min 0.110 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Peter Mayer' #?# X-ray operator _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 123(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation '0.8_mm' _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? _cell_length_a 14.1238(6) _cell_length_b 7.9707(4) _cell_length_c 15.8261(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.1161(13) _cell_angle_gamma 90.00 _cell_volume 1683.40(13) _cell_measurement_temperature 123(2) #?# in K _cell_measurement_reflns_used 108 _cell_measurement_theta_min 2.9138 _cell_measurement_theta_max 24.3149 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9360 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 29650 #xl _diffrn_reflns_av_R_equivalents 0.0499 #xl _diffrn_reflns_av_sigmaI/netI 0.0255 #xl _diffrn_reflns_limit_h_min -17 #xl _diffrn_reflns_limit_h_max 17 #xl _diffrn_reflns_limit_k_min -9 #xl _diffrn_reflns_limit_k_max 9 #xl _diffrn_reflns_limit_l_min -18 #xl _diffrn_reflns_limit_l_max 19 #xl _diffrn_reflns_theta_min 2.98 #xl _diffrn_reflns_theta_max 25.36 #xl _diffrn_measured_fraction_theta_max 0.995 #xl _diffrn_reflns_theta_full 25.36 #xl _diffrn_measured_fraction_theta_full 0.995 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3075 #xl _reflns_number_gt 2438 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.7809P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 3075 #xl _refine_ls_number_parameters 237 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0524 #xl _refine_ls_R_factor_gt 0.0355 #xl _refine_ls_wR_factor_ref 0.0884 #xl _refine_ls_wR_factor_gt 0.0809 #xl _refine_ls_goodness_of_fit_ref 1.027 #xl _refine_ls_restrained_S_all 1.027 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.223 #xl _refine_diff_density_min -0.184 #xl _refine_diff_density_rms 0.039 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.60722(13) 0.8298(3) 0.68820(10) 0.0349(4) Uani 1 1 d . . . H1A H 0.6770 0.7917 0.7068 0.052 Uiso 1 1 calc R . . H1B H 0.5727 0.7761 0.7256 0.052 Uiso 1 1 calc R . . H1C H 0.6056 0.9519 0.6950 0.052 Uiso 1 1 calc R . . C2 C 0.59776(11) 0.7000(2) 0.54286(10) 0.0226(4) Uani 1 1 d . . . H2 H 0.6648 0.6599 0.5612 0.027 Uiso 1 1 calc R . . C4 C 0.34036(12) 0.7796(2) 0.39894(11) 0.0261(4) Uani 1 1 d . . . H4 H 0.3233 0.7338 0.3404 0.031 Uiso 1 1 calc R . . C5 C 0.27083(13) 0.8678(2) 0.42541(12) 0.0330(4) Uani 1 1 d . . . H5 H 0.2053 0.8832 0.3842 0.040 Uiso 1 1 calc R . . C8 C 0.45756(11) 0.82546(19) 0.54654(10) 0.0203(3) Uani 1 1 d . . . C9 C 0.43642(11) 0.75935(18) 0.46051(10) 0.0191(3) Uani 1 1 d . . . C6 C 0.29459(13) 0.9349(2) 0.51135(12) 0.0325(4) Uani 1 1 d . . . H6 H 0.2450 0.9960 0.5270 0.039 Uiso 1 1 calc R . . C7 C 0.38844(12) 0.9146(2) 0.57411(11) 0.0272(4) Uani 1 1 d . . . H7 H 0.4048 0.9591 0.6328 0.033 Uiso 1 1 calc R . . C10 C 0.53755(11) 0.60034(19) 0.38152(9) 0.0189(3) Uani 1 1 d . . . H10 H 0.4794 0.6058 0.3300 0.023 Uiso 1 1 calc R . . C11 C 0.61788(11) 0.51620(19) 0.36818(9) 0.0185(3) Uani 1 1 d . . . C13 C 0.74731(14) 0.3174(2) 0.23082(11) 0.0296(4) Uani 1 1 d . . . H13 H 0.8133 0.2755 0.2426 0.036 Uiso 1 1 calc R . . C15 C 0.58107(13) 0.3775(2) 0.12929(11) 0.0306(4) Uani 1 1 d . . . H15 H 0.5348 0.3728 0.0702 0.037 Uiso 1 1 calc R . . C14 C 0.67761(14) 0.3143(2) 0.14610(11) 0.0314(4) Uani 1 1 d . . . H14 H 0.6957 0.2681 0.0982 0.038 Uiso 1 1 calc R . . C17 C 0.62001(11) 0.45070(18) 0.28275(10) 0.0198(3) Uani 1 1 d . . . C16 C 0.55094(12) 0.4471(2) 0.19652(10) 0.0244(4) Uani 1 1 d . . . H16 H 0.4853 0.4909 0.1843 0.029 Uiso 1 1 calc R . . C18 C 0.71594(12) 0.38481(19) 0.29784(10) 0.0222(3) Uani 1 1 d . . . C19 C 0.87423(12) 0.3544(2) 0.43053(12) 0.0365(4) Uani 1 1 d . . . H19A H 0.8959 0.3820 0.4944 0.055 Uiso 1 1 calc R . . H19B H 0.9166 0.4137 0.4021 0.055 Uiso 1 1 calc R . . H19C H 0.8802 0.2331 0.4232 0.055 Uiso 1 1 calc R . . C12 C 0.71327(11) 0.48052(19) 0.42963(10) 0.0215(3) Uani 1 1 d . . . H12 H 0.7340 0.5066 0.4916 0.026 Uiso 1 1 calc R . . B1 B 0.10862(13) 0.3263(2) 0.34820(12) 0.0245(4) Uani 1 1 d . . . N1 N 0.55713(9) 0.78487(17) 0.59467(8) 0.0232(3) Uani 1 1 d . . . N2 N 0.77021(9) 0.40522(16) 0.38871(8) 0.0233(3) Uani 1 1 d . . . F1 F 0.01465(7) 0.36676(13) 0.28981(6) 0.0349(3) Uani 1 1 d . . . F2 F 0.14913(7) 0.19691(14) 0.31120(6) 0.0397(3) Uani 1 1 d . . . F3 F 0.17262(8) 0.46399(14) 0.36197(6) 0.0443(3) Uani 1 1 d . . . C3 C 0.52728(11) 0.67788(19) 0.45680(10) 0.0185(3) Uani 1 1 d . . . F4 F 0.10231(7) 0.27412(14) 0.42959(6) 0.0395(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0336(10) 0.0520(12) 0.0189(8) -0.0100(8) 0.0082(7) -0.0079(9) C2 0.0187(8) 0.0285(9) 0.0220(8) -0.0012(7) 0.0086(6) -0.0022(7) C4 0.0264(9) 0.0279(9) 0.0228(8) -0.0005(7) 0.0066(7) 0.0015(7) C5 0.0261(9) 0.0352(10) 0.0361(10) 0.0033(8) 0.0081(8) 0.0089(8) C8 0.0222(8) 0.0189(8) 0.0223(8) -0.0004(6) 0.0106(6) -0.0037(6) C9 0.0221(8) 0.0160(8) 0.0211(8) 0.0020(6) 0.0097(6) -0.0015(6) C6 0.0324(10) 0.0280(9) 0.0431(10) 0.0010(8) 0.0206(8) 0.0072(8) C7 0.0363(10) 0.0223(9) 0.0292(9) -0.0038(7) 0.0192(8) -0.0039(7) C10 0.0203(8) 0.0180(8) 0.0178(7) 0.0027(6) 0.0055(6) -0.0043(6) C11 0.0210(8) 0.0177(8) 0.0176(7) 0.0000(6) 0.0074(6) -0.0032(6) C13 0.0392(10) 0.0204(8) 0.0364(10) -0.0002(7) 0.0220(8) 0.0049(7) C15 0.0465(11) 0.0244(9) 0.0204(8) -0.0031(7) 0.0102(7) -0.0041(8) C14 0.0523(11) 0.0209(9) 0.0281(9) -0.0025(7) 0.0229(8) 0.0019(8) C17 0.0249(8) 0.0153(7) 0.0211(8) 0.0004(6) 0.0102(6) -0.0031(6) C16 0.0287(9) 0.0214(8) 0.0224(8) -0.0004(7) 0.0076(7) -0.0012(7) C18 0.0286(9) 0.0163(8) 0.0240(8) 0.0003(6) 0.0119(7) -0.0007(7) C19 0.0239(9) 0.0425(11) 0.0401(10) -0.0018(9) 0.0065(8) 0.0110(8) C12 0.0235(8) 0.0205(8) 0.0205(8) -0.0013(6) 0.0073(7) -0.0012(6) B1 0.0217(9) 0.0316(10) 0.0177(9) 0.0022(8) 0.0031(7) -0.0026(8) N1 0.0227(7) 0.0295(7) 0.0182(6) -0.0047(6) 0.0076(5) -0.0057(6) N2 0.0208(7) 0.0234(7) 0.0266(7) -0.0002(6) 0.0089(6) 0.0030(6) F1 0.0249(5) 0.0439(6) 0.0301(5) 0.0043(5) 0.0010(4) 0.0024(4) F2 0.0326(6) 0.0522(7) 0.0349(6) -0.0047(5) 0.0119(5) 0.0063(5) F3 0.0444(6) 0.0448(7) 0.0304(6) 0.0072(5) -0.0059(5) -0.0193(5) C3 0.0184(7) 0.0188(8) 0.0190(8) 0.0011(6) 0.0069(6) -0.0025(6) F4 0.0435(6) 0.0542(7) 0.0217(5) 0.0068(5) 0.0120(4) -0.0023(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.461(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.329(2) . ? C2 C3 1.410(2) . ? C2 H2 0.9500 . ? C4 C5 1.380(2) . ? C4 C9 1.397(2) . ? C4 H4 0.9500 . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C8 C7 1.388(2) . ? C8 C9 1.398(2) . ? C8 N1 1.400(2) . ? C9 C3 1.456(2) . ? C6 C7 1.381(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C10 C3 1.391(2) . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 C12 1.408(2) . ? C11 C17 1.459(2) . ? C13 C14 1.380(2) . ? C13 C18 1.385(2) . ? C13 H13 0.9500 . ? C15 C16 1.384(2) . ? C15 C14 1.395(3) . ? C15 H15 0.9500 . ? C14 H14 0.9500 . ? C17 C16 1.394(2) . ? C17 C18 1.399(2) . ? C16 H16 0.9500 . ? C18 N2 1.400(2) . ? C19 N2 1.457(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C12 N2 1.330(2) . ? C12 H12 0.9500 . ? B1 F4 1.384(2) . ? B1 F1 1.384(2) . ? B1 F3 1.393(2) . ? B1 F2 1.398(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.39(13) . . ? N1 C2 H2 124.8 . . ? C3 C2 H2 124.8 . . ? C5 C4 C9 118.19(15) . . ? C5 C4 H4 120.9 . . ? C9 C4 H4 120.9 . . ? C4 C5 C6 121.54(16) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C8 C9 123.45(14) . . ? C7 C8 N1 129.17(14) . . ? C9 C8 N1 107.38(13) . . ? C4 C9 C8 119.00(14) . . ? C4 C9 C3 133.69(14) . . ? C8 C9 C3 107.31(13) . . ? C7 C6 C5 121.56(16) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 116.24(15) . . ? C6 C7 H7 121.9 . . ? C8 C7 H7 121.9 . . ? C3 C10 C11 131.49(14) . . ? C3 C10 H10 114.3 . . ? C11 C10 H10 114.3 . . ? C10 C11 C12 129.44(14) . . ? C10 C11 C17 125.31(13) . . ? C12 C11 C17 105.21(13) . . ? C14 C13 C18 116.48(16) . . ? C14 C13 H13 121.8 . . ? C18 C13 H13 121.8 . . ? C16 C15 C14 121.68(15) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C13 C14 C15 121.38(15) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C17 C18 119.18(14) . . ? C16 C17 C11 134.00(14) . . ? C18 C17 C11 106.79(13) . . ? C15 C16 C17 117.91(15) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? C13 C18 C17 123.36(15) . . ? C13 C18 N2 128.82(15) . . ? C17 C18 N2 107.79(13) . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C12 C11 110.44(13) . . ? N2 C12 H12 124.8 . . ? C11 C12 H12 124.8 . . ? F4 B1 F1 110.58(14) . . ? F4 B1 F3 109.12(13) . . ? F1 B1 F3 110.61(14) . . ? F4 B1 F2 109.16(14) . . ? F1 B1 F2 109.07(13) . . ? F3 B1 F2 108.25(14) . . ? C2 N1 C8 109.98(12) . . ? C2 N1 C1 125.88(13) . . ? C8 N1 C1 124.14(13) . . ? C12 N2 C18 109.74(12) . . ? C12 N2 C19 125.80(13) . . ? C18 N2 C19 124.44(13) . . ? C10 C3 C2 130.09(14) . . ? C10 C3 C9 124.96(13) . . ? C2 C3 C9 104.94(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C4 C5 C6 -0.4(3) . . . . ? C5 C4 C9 C8 1.4(2) . . . . ? C5 C4 C9 C3 -179.33(16) . . . . ? C7 C8 C9 C4 -1.6(2) . . . . ? N1 C8 C9 C4 178.71(13) . . . . ? C7 C8 C9 C3 179.00(14) . . . . ? N1 C8 C9 C3 -0.70(16) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 C8 0.6(2) . . . . ? C9 C8 C7 C6 0.5(2) . . . . ? N1 C8 C7 C6 -179.84(15) . . . . ? C3 C10 C11 C12 2.1(3) . . . . ? C3 C10 C11 C17 -175.39(15) . . . . ? C18 C13 C14 C15 0.6(2) . . . . ? C16 C15 C14 C13 0.4(3) . . . . ? C10 C11 C17 C16 -1.3(3) . . . . ? C12 C11 C17 C16 -179.34(16) . . . . ? C10 C11 C17 C18 176.57(14) . . . . ? C12 C11 C17 C18 -1.45(16) . . . . ? C14 C15 C16 C17 -0.7(2) . . . . ? C18 C17 C16 C15 0.0(2) . . . . ? C11 C17 C16 C15 177.71(16) . . . . ? C14 C13 C18 C17 -1.3(2) . . . . ? C14 C13 C18 N2 -179.35(15) . . . . ? C16 C17 C18 C13 1.0(2) . . . . ? C11 C17 C18 C13 -177.24(15) . . . . ? C16 C17 C18 N2 179.42(13) . . . . ? C11 C17 C18 N2 1.16(16) . . . . ? C10 C11 C12 N2 -176.66(15) . . . . ? C17 C11 C12 N2 1.25(17) . . . . ? C3 C2 N1 C8 -0.32(18) . . . . ? C3 C2 N1 C1 179.38(15) . . . . ? C7 C8 N1 C2 -179.03(16) . . . . ? C9 C8 N1 C2 0.65(17) . . . . ? C7 C8 N1 C1 1.3(3) . . . . ? C9 C8 N1 C1 -179.06(14) . . . . ? C11 C12 N2 C18 -0.56(18) . . . . ? C11 C12 N2 C19 178.08(15) . . . . ? C13 C18 N2 C12 177.88(16) . . . . ? C17 C18 N2 C12 -0.40(17) . . . . ? C13 C18 N2 C19 -0.8(3) . . . . ? C17 C18 N2 C19 -179.07(15) . . . . ? C11 C10 C3 C2 2.6(3) . . . . ? C11 C10 C3 C9 -178.89(15) . . . . ? N1 C2 C3 C10 178.61(15) . . . . ? N1 C2 C3 C9 -0.12(17) . . . . ? C4 C9 C3 C10 2.4(3) . . . . ? C8 C9 C3 C10 -178.30(14) . . . . ? C4 C9 C3 C2 -178.78(17) . . . . ? C8 C9 C3 C2 0.51(16) . . . . ? _audit_block_code C19H17N2_BF4_rv253_mayr _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C19 H17 N2, B F4' _chemical_formula_sum 'C19 H17 B F4 N2' _chemical_formula_weight 360.156 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.42108(11) _exptl_crystal_F_000 744 data_rv330 #?# MeasurementCode _audit_update_record 21-Jan-14 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour yellow _exptl_crystal_size_max 0.137 #?# in millimeters _exptl_crystal_size_mid 0.114 #?# in millimeters _exptl_crystal_size_min 0.095 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Peter Mayer' #?# X-ray operator _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 100(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation '0.8_mm' _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? _cell_length_a 7.6174(4) _cell_length_b 8.8763(5) _cell_length_c 15.4323(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.703(2) _cell_angle_gamma 90.00 _cell_volume 923.83(8) _cell_measurement_temperature 100(2) #?# in K _cell_measurement_reflns_used 122 _cell_measurement_theta_min 3.7342 _cell_measurement_theta_max 30.4481 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9258 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 18399 #xl _diffrn_reflns_av_R_equivalents 0.0251 #xl _diffrn_reflns_av_sigmaI/netI 0.0192 #xl _diffrn_reflns_limit_h_min -9 #xl _diffrn_reflns_limit_h_max 9 #xl _diffrn_reflns_limit_k_min -11 #xl _diffrn_reflns_limit_k_max 11 #xl _diffrn_reflns_limit_l_min -16 #xl _diffrn_reflns_limit_l_max 19 #xl _diffrn_reflns_theta_min 3.10 #xl _diffrn_reflns_theta_max 26.41 #xl _diffrn_measured_fraction_theta_max 0.996 #xl _diffrn_reflns_theta_full 26.42 #xl _diffrn_measured_fraction_theta_full 0.996 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P c' _symmetry_space_group_name_Hall 'P -2yc' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 3566 #xl _reflns_number_gt 3416 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.2708P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' #xl _refine_ls_abs_structure_Flack 0.0(5) #xl _refine_ls_number_reflns 3566 #xl _refine_ls_number_parameters 258 #xl _refine_ls_number_restraints 2 #xl _refine_ls_R_factor_all 0.0330 #xl _refine_ls_R_factor_gt 0.0308 #xl _refine_ls_wR_factor_ref 0.0798 #xl _refine_ls_wR_factor_gt 0.0779 #xl _refine_ls_goodness_of_fit_ref 1.073 #xl _refine_ls_restrained_S_all 1.073 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.303 #xl _refine_diff_density_min -0.169 #xl _refine_diff_density_rms 0.040 #xl _refine_special_details ; refined as racemic twin ; _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.36405(19) -0.08085(16) 0.43964(10) 0.0178(3) Uani 1 1 d . . . N2 N -0.23812(19) -0.11826(16) -0.06938(10) 0.0163(3) Uani 1 1 d . . . C1 C 0.5141(2) -0.1107(2) 0.54021(12) 0.0235(4) Uani 1 1 d . . . H1A H 0.4499 -0.1209 0.5821 0.035 Uiso 1 1 calc R . . H1B H 0.6089 -0.0271 0.5637 0.035 Uiso 1 1 calc R . . H1C H 0.5843 -0.2043 0.5422 0.035 Uiso 1 1 calc R . . C2 C 0.2999(2) -0.17748(18) 0.36410(12) 0.0167(3) Uani 1 1 d . . . C3 C 0.1620(2) -0.10210(17) 0.27752(12) 0.0146(3) Uani 1 1 d . . . C4 C 0.0134(2) 0.17105(18) 0.26284(12) 0.0169(3) Uani 1 1 d . . . H4 H -0.0792 0.1674 0.1953 0.020 Uiso 1 1 calc R . . C5 C 0.0268(2) 0.29807(19) 0.31861(13) 0.0206(3) Uani 1 1 d . . . H5 H -0.0555 0.3825 0.2881 0.025 Uiso 1 1 calc R . . C6 C 0.1590(3) 0.30375(19) 0.41850(13) 0.0224(4) Uani 1 1 d . . . H6 H 0.1658 0.3922 0.4546 0.027 Uiso 1 1 calc R . . C7 C 0.2802(2) 0.18246(19) 0.46582(13) 0.0198(3) Uani 1 1 d . . . H7 H 0.3689 0.1849 0.5340 0.024 Uiso 1 1 calc R . . C8 C 0.2661(2) 0.05680(18) 0.40905(12) 0.0171(3) Uani 1 1 d . . . C9 C 0.1390(2) 0.04895(18) 0.30833(12) 0.0156(3) Uani 1 1 d . . . C10 C 0.0708(3) -0.17504(17) 0.18698(13) 0.0154(3) Uani 1 1 d . . . H10 H 0.0768 -0.2819 0.1903 0.019 Uiso 1 1 calc R . . C11 C -0.0277(2) -0.11618(17) 0.09252(12) 0.0152(3) Uani 1 1 d . . . C14 C -0.0593(2) 0.2687(2) -0.07338(13) 0.0214(4) Uani 1 1 d . . . H14 H -0.0743 0.3523 -0.1147 0.026 Uiso 1 1 calc R . . C13 C -0.1744(2) 0.14106(19) -0.11257(13) 0.0186(3) Uani 1 1 d . . . H13 H -0.2661 0.1343 -0.1802 0.022 Uiso 1 1 calc R . . C17 C -0.0160(2) 0.02925(18) 0.05258(11) 0.0149(3) Uani 1 1 d . . . C18 C -0.1493(2) 0.02389(18) -0.04842(11) 0.0154(3) Uani 1 1 d . . . C15 C 0.0781(2) 0.27676(19) 0.02551(13) 0.0205(3) Uani 1 1 d . . . H15 H 0.1567 0.3649 0.0501 0.025 Uiso 1 1 calc R . . C16 C 0.1019(2) 0.15784(18) 0.08885(12) 0.0166(3) Uani 1 1 d . . . H16 H 0.1972 0.1639 0.1559 0.020 Uiso 1 1 calc R . . C12 C -0.1623(2) -0.20423(17) 0.01128(12) 0.0162(3) Uani 1 1 d . . . C19 C 0.3745(3) -0.33415(19) 0.37601(13) 0.0218(3) Uani 1 1 d . . . H19A H 0.5091 -0.3340 0.3830 0.033 Uiso 1 1 calc R . . H19B H 0.2873 -0.3935 0.3184 0.033 Uiso 1 1 calc R . . H19C H 0.3763 -0.3787 0.4345 0.033 Uiso 1 1 calc R . . C20 C -0.2211(3) -0.36382(19) 0.00998(13) 0.0217(4) Uani 1 1 d . . . H20A H -0.3471 -0.3683 0.0125 0.033 Uiso 1 1 calc R . . H20B H -0.1185 -0.4165 0.0668 0.033 Uiso 1 1 calc R . . H20C H -0.2363 -0.4122 -0.0502 0.033 Uiso 1 1 calc R . . C21 C -0.3919(2) -0.1620(2) -0.16694(12) 0.0215(4) Uani 1 1 d . . . H21A H -0.3298 -0.1889 -0.2080 0.032 Uiso 1 1 calc R . . H21B H -0.4832 -0.0775 -0.1968 0.032 Uiso 1 1 calc R . . H21C H -0.4653 -0.2488 -0.1613 0.032 Uiso 1 1 calc R . . F1 F 0.61722(16) 0.50064(12) 0.77476(8) 0.0289(2) Uani 1 1 d . . . F2 F 0.63224(19) 0.31075(13) 0.67932(9) 0.0367(3) Uani 1 1 d . . . F3 F 0.54720(18) 0.54632(13) 0.61704(8) 0.0356(3) Uani 1 1 d . . . F4 F 0.33442(16) 0.40956(14) 0.64950(9) 0.0377(3) Uani 1 1 d . . . B1 B 0.5328(3) 0.4415(2) 0.68059(15) 0.0207(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0161(6) 0.0222(7) 0.0137(7) 0.0019(5) 0.0057(5) -0.0043(5) N2 0.0172(6) 0.0187(7) 0.0133(7) -0.0020(5) 0.0073(5) 0.0020(5) C1 0.0182(8) 0.0336(9) 0.0128(8) 0.0055(7) 0.0023(7) -0.0048(7) C2 0.0149(7) 0.0213(8) 0.0160(8) 0.0036(6) 0.0090(6) -0.0020(6) C3 0.0142(7) 0.0165(7) 0.0142(8) 0.0016(6) 0.0076(6) -0.0003(6) C4 0.0139(7) 0.0192(8) 0.0170(8) -0.0014(6) 0.0067(6) -0.0005(6) C5 0.0215(8) 0.0185(8) 0.0255(9) -0.0022(7) 0.0141(7) -0.0008(6) C6 0.0269(9) 0.0204(8) 0.0251(9) -0.0098(7) 0.0164(7) -0.0071(7) C7 0.0199(8) 0.0257(9) 0.0142(8) -0.0052(6) 0.0083(6) -0.0088(7) C8 0.0152(7) 0.0213(8) 0.0167(8) 0.0013(6) 0.0090(6) -0.0047(6) C9 0.0145(7) 0.0192(8) 0.0156(8) -0.0021(6) 0.0092(6) -0.0035(6) C10 0.0162(6) 0.0138(7) 0.0175(7) 0.0008(6) 0.0089(5) 0.0013(6) C11 0.0143(7) 0.0163(7) 0.0156(8) -0.0017(6) 0.0076(6) 0.0017(6) C14 0.0236(8) 0.0208(8) 0.0239(9) 0.0091(7) 0.0145(7) 0.0067(7) C13 0.0173(7) 0.0229(8) 0.0156(8) 0.0028(6) 0.0076(6) 0.0056(6) C17 0.0136(7) 0.0183(7) 0.0141(7) 0.0000(6) 0.0075(6) 0.0040(6) C18 0.0142(7) 0.0205(8) 0.0128(8) -0.0017(6) 0.0073(6) 0.0030(6) C15 0.0189(8) 0.0173(8) 0.0277(10) 0.0008(6) 0.0128(7) 0.0001(6) C16 0.0144(7) 0.0206(8) 0.0164(8) 0.0000(6) 0.0084(6) 0.0012(6) C12 0.0156(7) 0.0192(8) 0.0155(8) -0.0014(6) 0.0088(6) 0.0024(6) C19 0.0238(8) 0.0217(8) 0.0196(9) 0.0064(7) 0.0099(7) 0.0032(7) C20 0.0254(8) 0.0203(8) 0.0188(9) -0.0059(6) 0.0098(7) -0.0046(7) C21 0.0177(7) 0.0286(9) 0.0133(8) -0.0044(7) 0.0030(6) 0.0031(7) F1 0.0323(5) 0.0290(5) 0.0214(5) -0.0072(4) 0.0090(4) -0.0056(4) F2 0.0543(7) 0.0293(6) 0.0242(6) 0.0049(5) 0.0163(5) 0.0144(5) F3 0.0456(7) 0.0338(6) 0.0346(7) 0.0167(5) 0.0247(5) 0.0092(5) F4 0.0297(6) 0.0491(7) 0.0295(6) -0.0027(5) 0.0097(5) -0.0138(5) B1 0.0255(10) 0.0187(9) 0.0160(9) 0.0026(7) 0.0081(8) -0.0015(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.343(2) . ? N1 C8 1.395(2) . ? N1 C1 1.462(2) . ? N2 C12 1.341(2) . ? N2 C18 1.397(2) . ? N2 C21 1.466(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.425(2) . ? C2 C19 1.481(2) . ? C3 C10 1.397(2) . ? C3 C9 1.460(2) . ? C4 C5 1.393(2) . ? C4 C9 1.399(2) . ? C4 H4 0.9500 . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C6 C7 1.385(2) . ? C6 H6 0.9500 . ? C7 C8 1.391(2) . ? C7 H7 0.9500 . ? C8 C9 1.400(2) . ? C10 C11 1.394(2) . ? C10 H10 0.9500 . ? C11 C12 1.428(2) . ? C11 C17 1.451(2) . ? C14 C13 1.388(2) . ? C14 C15 1.394(3) . ? C14 H14 0.9500 . ? C13 C18 1.386(2) . ? C13 H13 0.9500 . ? C17 C16 1.399(2) . ? C17 C18 1.411(2) . ? C15 C16 1.392(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C12 C20 1.483(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? F1 B1 1.390(2) . ? F2 B1 1.391(2) . ? F3 B1 1.393(2) . ? F4 B1 1.386(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C8 110.14(13) . . ? C2 N1 C1 126.51(14) . . ? C8 N1 C1 123.35(14) . . ? C12 N2 C18 110.23(13) . . ? C12 N2 C21 126.63(14) . . ? C18 N2 C21 123.14(14) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.02(14) . . ? N1 C2 C19 121.89(15) . . ? C3 C2 C19 129.06(15) . . ? C10 C3 C2 121.82(15) . . ? C10 C3 C9 132.23(15) . . ? C2 C3 C9 105.88(14) . . ? C5 C4 C9 118.70(15) . . ? C5 C4 H4 120.6 . . ? C9 C4 H4 120.6 . . ? C4 C5 C6 121.30(16) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 121.05(15) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 116.99(16) . . ? C6 C7 H7 121.5 . . ? C8 C7 H7 121.5 . . ? C7 C8 N1 128.07(15) . . ? C7 C8 C9 123.38(15) . . ? N1 C8 C9 108.51(14) . . ? C4 C9 C8 118.51(15) . . ? C4 C9 C3 134.86(15) . . ? C8 C9 C3 106.35(14) . . ? C11 C10 C3 130.37(14) . . ? C11 C10 H10 114.8 . . ? C3 C10 H10 114.8 . . ? C10 C11 C12 122.04(14) . . ? C10 C11 C17 131.92(15) . . ? C12 C11 C17 105.95(14) . . ? C13 C14 C15 121.30(16) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C18 C13 C14 116.85(15) . . ? C18 C13 H13 121.6 . . ? C14 C13 H13 121.6 . . ? C16 C17 C18 117.91(14) . . ? C16 C17 C11 135.31(15) . . ? C18 C17 C11 106.54(14) . . ? C13 C18 N2 128.39(14) . . ? C13 C18 C17 123.59(15) . . ? N2 C18 C17 107.97(13) . . ? C16 C15 C14 121.08(16) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 119.21(15) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? N2 C12 C11 109.11(13) . . ? N2 C12 C20 122.28(14) . . ? C11 C12 C20 128.60(15) . . ? C2 C19 H19A 109.5 . . ? C2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C12 C20 H20A 109.5 . . ? C12 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C12 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? F4 B1 F1 109.82(15) . . ? F4 B1 F2 109.73(15) . . ? F1 B1 F2 109.86(15) . . ? F4 B1 F3 108.84(15) . . ? F1 B1 F3 109.55(15) . . ? F2 B1 F3 109.03(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C2 C3 3.38(18) . . . . ? C1 N1 C2 C3 -176.55(15) . . . . ? C8 N1 C2 C19 -178.23(14) . . . . ? C1 N1 C2 C19 1.8(2) . . . . ? N1 C2 C3 C10 179.85(14) . . . . ? C19 C2 C3 C10 1.6(3) . . . . ? N1 C2 C3 C9 -3.08(17) . . . . ? C19 C2 C3 C9 178.68(16) . . . . ? C9 C4 C5 C6 -1.5(2) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C5 C6 C7 C8 1.0(2) . . . . ? C6 C7 C8 N1 -176.70(15) . . . . ? C6 C7 C8 C9 0.7(2) . . . . ? C2 N1 C8 C7 175.40(16) . . . . ? C1 N1 C8 C7 -4.7(2) . . . . ? C2 N1 C8 C9 -2.30(18) . . . . ? C1 N1 C8 C9 177.63(14) . . . . ? C5 C4 C9 C8 3.1(2) . . . . ? C5 C4 C9 C3 175.99(17) . . . . ? C7 C8 C9 C4 -2.7(2) . . . . ? N1 C8 C9 C4 175.09(14) . . . . ? C7 C8 C9 C3 -177.52(14) . . . . ? N1 C8 C9 C3 0.31(17) . . . . ? C10 C3 C9 C4 4.8(3) . . . . ? C2 C3 C9 C4 -171.89(18) . . . . ? C10 C3 C9 C8 178.28(17) . . . . ? C2 C3 C9 C8 1.64(16) . . . . ? C2 C3 C10 C11 -162.78(16) . . . . ? C9 C3 C10 C11 21.0(3) . . . . ? C3 C10 C11 C12 -160.44(16) . . . . ? C3 C10 C11 C17 23.3(3) . . . . ? C15 C14 C13 C18 1.4(2) . . . . ? C10 C11 C17 C16 5.4(3) . . . . ? C12 C11 C17 C16 -171.23(18) . . . . ? C10 C11 C17 C18 179.33(16) . . . . ? C12 C11 C17 C18 2.67(16) . . . . ? C14 C13 C18 N2 -176.50(15) . . . . ? C14 C13 C18 C17 0.5(2) . . . . ? C12 N2 C18 C13 174.59(15) . . . . ? C21 N2 C18 C13 -5.4(2) . . . . ? C12 N2 C18 C17 -2.76(18) . . . . ? C21 N2 C18 C17 177.28(14) . . . . ? C16 C17 C18 C13 -2.4(2) . . . . ? C11 C17 C18 C13 -177.59(14) . . . . ? C16 C17 C18 N2 175.06(13) . . . . ? C11 C17 C18 N2 -0.09(17) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C14 C15 C16 C17 -0.9(2) . . . . ? C18 C17 C16 C15 2.6(2) . . . . ? C11 C17 C16 C15 175.94(16) . . . . ? C18 N2 C12 C11 4.52(18) . . . . ? C21 N2 C12 C11 -175.52(14) . . . . ? C18 N2 C12 C20 -176.78(14) . . . . ? C21 N2 C12 C20 3.2(2) . . . . ? C10 C11 C12 N2 178.50(14) . . . . ? C17 C11 C12 N2 -4.43(17) . . . . ? C10 C11 C12 C20 -0.1(3) . . . . ? C17 C11 C12 C20 176.98(16) . . . . ? _audit_block_code C21H21N2_BF4_rv330_mayr _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C21 H21 N2, B F4' _chemical_formula_sum 'C21 H21 B F4 N2' _chemical_formula_weight 388.210 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 2 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.39560(12) _exptl_crystal_F_000 404 data_rv414 #?# MeasurementCode _audit_update_record 06-Nov-13 _chemical_name_common ? #?# use for preliminary identification _chemical_compound_source ? _exptl_crystal_description block #?# e.g.: needle, platelet; prisma _exptl_crystal_colour colourless _exptl_crystal_size_max 0.180 #?# in millimeters _exptl_crystal_size_mid 0.150 #?# in millimeters _exptl_crystal_size_min 0.120 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Peter Mayer' #?# X-ray operator _audit_creation_date ? #?# style: 18-Aug-1998 _diffrn_ambient_temperature 173(2) #?# in K _diffrn_source_type 'Bruker TXS' _diffrn_source_power 2.5 #?# in kW _diffrn_source_voltage 50 #?# in kV _diffrn_source_current 50 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_collimation '0.8_mm' _diffrn_measurement_device 'fixed-chi three-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8Venture' _diffrn_measurement_method 'mix of phi and omega scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_special_details ? _diffrn_orient_matrix_type ? _diffrn_orient_matrix_UB_11 ? _diffrn_orient_matrix_UB_12 ? _diffrn_orient_matrix_UB_13 ? _diffrn_orient_matrix_UB_21 ? _diffrn_orient_matrix_UB_22 ? _diffrn_orient_matrix_UB_23 ? _diffrn_orient_matrix_UB_31 ? _diffrn_orient_matrix_UB_32 ? _diffrn_orient_matrix_UB_33 ? _cell_length_a 9.3452(6) _cell_length_b 8.5145(5) _cell_length_c 16.8450(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.7950(19) _cell_angle_gamma 90.00 _cell_volume 1289.74(14) _cell_measurement_temperature 173(2) #?# in K _cell_measurement_reflns_used 7354 _cell_measurement_theta_min 2.8740 _cell_measurement_theta_max 26.1531 _cell_special_details ? _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9111 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _diffrn_reflns_number 22058 #xl _diffrn_reflns_av_R_equivalents 0.0365 #xl _diffrn_reflns_av_sigmaI/netI 0.0202 #xl _diffrn_reflns_limit_h_min -11 #xl _diffrn_reflns_limit_h_max 11 #xl _diffrn_reflns_limit_k_min -10 #xl _diffrn_reflns_limit_k_max 10 #xl _diffrn_reflns_limit_l_min -20 #xl _diffrn_reflns_limit_l_max 20 #xl _diffrn_reflns_theta_min 3.29 #xl _diffrn_reflns_theta_max 26.49 #xl _diffrn_measured_fraction_theta_max 0.995 #xl _diffrn_reflns_theta_full 26.33 #xl _diffrn_measured_fraction_theta_full 0.995 #xl _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _reflns_number_total 2619 #xl _reflns_number_gt 2161 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details ? #xl _refine_ls_abs_structure_Flack ? #xl _refine_ls_number_reflns 2619 #xl _refine_ls_number_parameters 174 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0534 #xl _refine_ls_R_factor_gt 0.0413 #xl _refine_ls_wR_factor_ref 0.1127 #xl _refine_ls_wR_factor_gt 0.1045 #xl _refine_ls_goodness_of_fit_ref 1.077 #xl _refine_ls_restrained_S_all 1.077 #xl _refine_ls_shift/su_max 0.000 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.417 #xl _refine_diff_density_min -0.211 #xl _refine_diff_density_rms 0.041 #xl _refine_special_details ? _computing_data_collection 'Bruker Instrument Service v3.0.21' _computing_cell_refinement 'APEX2 v2012.4-3 (Bruker AXS)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement ; Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. ; _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.03058(17) 0.20515(17) 0.54650(9) 0.0233(3) Uani 1 1 d . . . C1 C -0.08790(19) 0.0326(2) 0.63206(11) 0.0329(4) Uani 1 1 d . . . H1A H -0.1615 0.1107 0.6379 0.049 Uiso 1 1 calc R . . H1B H -0.0535 -0.0270 0.6835 0.049 Uiso 1 1 calc R . . H1C H -0.1334 -0.0392 0.5868 0.049 Uiso 1 1 calc R . . C3 C 0.17133(16) 0.25796(17) 0.54829(9) 0.0220(3) Uani 1 1 d . . . C5 C 0.48272(19) 0.1364(2) 0.73580(10) 0.0333(4) Uani 1 1 d . . . H5 H 0.5854 0.1488 0.7631 0.040 Uiso 1 1 calc R . . C4 C 0.42294(17) 0.21459(18) 0.66242(9) 0.0265(3) Uani 1 1 d . . . H4 H 0.4835 0.2800 0.6393 0.032 Uiso 1 1 calc R . . C7 C 0.2451(2) 0.0225(2) 0.73481(10) 0.0318(4) Uani 1 1 d . . . H7 H 0.1854 -0.0421 0.7589 0.038 Uiso 1 1 calc R . . C6 C 0.3955(2) 0.0394(2) 0.77087(10) 0.0355(4) Uani 1 1 d . . . H6 H 0.4407 -0.0158 0.8204 0.043 Uiso 1 1 calc R . . C9 C 0.27113(17) 0.19576(17) 0.62262(9) 0.0228(3) Uani 1 1 d . . . C8 C 0.18404(17) 0.10388(17) 0.66159(9) 0.0243(3) Uani 1 1 d . . . C11 C 0.31939(16) 0.34937(17) 0.45261(9) 0.0225(3) Uani 1 1 d . . . C10 C 0.20294(16) 0.35759(17) 0.48517(9) 0.0227(3) Uani 1 1 d . . . H10 H 0.1329 0.4385 0.4643 0.027 Uiso 1 1 calc R . . C13 C 0.5079(2) 0.3060(2) 0.34706(13) 0.0440(5) Uani 1 1 d . . . H13A H 0.6059 0.3431 0.3809 0.053 Uiso 1 1 calc R . . H13B H 0.5198 0.2719 0.2930 0.053 Uiso 1 1 calc R . . C12 C 0.32100(17) 0.46603(18) 0.38711(9) 0.0249(3) Uani 1 1 d . . . N1 N 0.03805(14) 0.11214(15) 0.61424(8) 0.0250(3) Uani 1 1 d . . . C14 C 0.4608(2) 0.1695(2) 0.38847(11) 0.0363(4) Uani 1 1 d . . . H14A H 0.5391 0.0877 0.3991 0.044 Uiso 1 1 calc R . . H14B H 0.3686 0.1239 0.3522 0.044 Uiso 1 1 calc R . . C15 C 0.43369(17) 0.22058(19) 0.46920(10) 0.0275(4) Uani 1 1 d . . . H15A H 0.3979 0.1304 0.4956 0.033 Uiso 1 1 calc R . . H15B H 0.5276 0.2589 0.5072 0.033 Uiso 1 1 calc R . . C16 C -0.11316(17) 0.2297(2) 0.48312(10) 0.0289(4) Uani 1 1 d . . . H16A H -0.1513 0.1284 0.4586 0.043 Uiso 1 1 calc R . . H16B H -0.0980 0.2998 0.4400 0.043 Uiso 1 1 calc R . . H16C H -0.1850 0.2769 0.5089 0.043 Uiso 1 1 calc R . . O1 O 0.40287(13) 0.43581(14) 0.33410(7) 0.0348(3) Uani 1 1 d . . . O2 O 0.24979(13) 0.58646(13) 0.37639(7) 0.0340(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0272(8) 0.0225(7) 0.0227(7) -0.0052(6) 0.0109(6) -0.0008(6) C1 0.0347(9) 0.0352(9) 0.0336(9) -0.0044(7) 0.0173(7) -0.0114(7) C3 0.0249(7) 0.0208(7) 0.0217(7) -0.0034(6) 0.0085(6) -0.0004(6) C5 0.0343(9) 0.0369(9) 0.0256(8) -0.0063(7) 0.0031(7) 0.0020(7) C4 0.0282(8) 0.0267(8) 0.0244(8) -0.0055(6) 0.0070(6) -0.0034(6) C7 0.0450(10) 0.0286(8) 0.0251(8) 0.0009(7) 0.0153(7) -0.0005(7) C6 0.0478(10) 0.0366(9) 0.0208(8) 0.0014(7) 0.0070(7) 0.0071(8) C9 0.0287(8) 0.0205(7) 0.0207(7) -0.0044(6) 0.0093(6) -0.0011(6) C8 0.0305(8) 0.0220(7) 0.0220(7) -0.0042(6) 0.0098(6) -0.0018(6) C11 0.0250(7) 0.0210(7) 0.0213(7) -0.0030(6) 0.0062(6) -0.0041(6) C10 0.0250(7) 0.0204(7) 0.0226(7) -0.0024(6) 0.0062(6) -0.0005(6) C13 0.0454(11) 0.0473(11) 0.0488(11) 0.0115(9) 0.0292(9) 0.0120(9) C12 0.0263(7) 0.0234(8) 0.0258(8) -0.0024(6) 0.0087(6) -0.0057(6) N1 0.0284(7) 0.0249(7) 0.0250(7) -0.0025(5) 0.0128(5) -0.0049(5) C14 0.0431(10) 0.0357(9) 0.0354(9) 0.0044(7) 0.0195(8) 0.0114(8) C15 0.0278(8) 0.0285(8) 0.0273(8) 0.0027(7) 0.0093(6) 0.0024(6) C16 0.0251(8) 0.0323(8) 0.0304(8) -0.0045(7) 0.0091(6) -0.0001(7) O1 0.0439(7) 0.0314(6) 0.0371(7) 0.0078(5) 0.0246(6) 0.0045(5) O2 0.0448(7) 0.0246(6) 0.0359(7) 0.0052(5) 0.0167(5) 0.0040(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.375(2) . ? C2 C3 1.383(2) . ? C2 C16 1.486(2) . ? C1 N1 1.4581(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C9 1.443(2) . ? C3 C10 1.452(2) . ? C5 C4 1.381(2) . ? C5 C6 1.399(3) . ? C5 H5 0.9500 . ? C4 C9 1.404(2) . ? C4 H4 0.9500 . ? C7 C6 1.379(3) . ? C7 C8 1.394(2) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? C9 C8 1.413(2) . ? C8 N1 1.382(2) . ? C11 C10 1.347(2) . ? C11 C12 1.488(2) . ? C11 C15 1.503(2) . ? C10 H10 0.9500 . ? C13 O1 1.455(2) . ? C13 C14 1.483(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C12 O2 1.2089(19) . ? C12 O1 1.3494(19) . ? C14 C15 1.514(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 109.64(13) . . ? N1 C2 C16 120.60(13) . . ? C3 C2 C16 129.70(14) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C3 C9 106.61(13) . . ? C2 C3 C10 123.78(14) . . ? C9 C3 C10 129.61(14) . . ? C4 C5 C6 121.49(16) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C4 C9 118.84(15) . . ? C5 C4 H4 120.6 . . ? C9 C4 H4 120.6 . . ? C6 C7 C8 117.44(15) . . ? C6 C7 H7 121.3 . . ? C8 C7 H7 121.3 . . ? C7 C6 C5 121.10(16) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C4 C9 C8 118.47(14) . . ? C4 C9 C3 134.67(14) . . ? C8 C9 C3 106.75(13) . . ? N1 C8 C7 129.64(14) . . ? N1 C8 C9 107.87(13) . . ? C7 C8 C9 122.50(15) . . ? C10 C11 C12 116.08(14) . . ? C10 C11 C15 125.04(14) . . ? C12 C11 C15 118.35(13) . . ? C11 C10 C3 128.00(14) . . ? C11 C10 H10 116.0 . . ? C3 C10 H10 116.0 . . ? O1 C13 C14 113.09(14) . . ? O1 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? O1 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O2 C12 O1 116.81(14) . . ? O2 C12 C11 124.11(14) . . ? O1 C12 C11 119.05(13) . . ? C2 N1 C8 109.11(12) . . ? C2 N1 C1 125.22(14) . . ? C8 N1 C1 125.65(13) . . ? C13 C14 C15 109.94(15) . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C11 C15 C14 109.10(13) . . ? C11 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? C11 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C2 C16 H16A 109.5 . . ? C2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 O1 C13 121.76(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C9 -1.09(16) . . . . ? C16 C2 C3 C9 -178.09(15) . . . . ? N1 C2 C3 C10 179.28(13) . . . . ? C16 C2 C3 C10 2.3(2) . . . . ? C6 C5 C4 C9 0.1(2) . . . . ? C8 C7 C6 C5 1.0(2) . . . . ? C4 C5 C6 C7 -2.3(3) . . . . ? C5 C4 C9 C8 3.2(2) . . . . ? C5 C4 C9 C3 178.83(16) . . . . ? C2 C3 C9 C4 -174.61(16) . . . . ? C10 C3 C9 C4 5.0(3) . . . . ? C2 C3 C9 C8 1.34(16) . . . . ? C10 C3 C9 C8 -179.07(14) . . . . ? C6 C7 C8 N1 -177.84(15) . . . . ? C6 C7 C8 C9 2.6(2) . . . . ? C4 C9 C8 N1 175.63(13) . . . . ? C3 C9 C8 N1 -1.10(16) . . . . ? C4 C9 C8 C7 -4.7(2) . . . . ? C3 C9 C8 C7 178.58(14) . . . . ? C12 C11 C10 C3 178.80(14) . . . . ? C15 C11 C10 C3 7.3(2) . . . . ? C2 C3 C10 C11 -139.90(17) . . . . ? C9 C3 C10 C11 40.6(2) . . . . ? C10 C11 C12 O2 19.1(2) . . . . ? C15 C11 C12 O2 -168.79(14) . . . . ? C10 C11 C12 O1 -158.83(14) . . . . ? C15 C11 C12 O1 13.3(2) . . . . ? C3 C2 N1 C8 0.42(17) . . . . ? C16 C2 N1 C8 177.74(13) . . . . ? C3 C2 N1 C1 -178.44(14) . . . . ? C16 C2 N1 C1 -1.1(2) . . . . ? C7 C8 N1 C2 -179.20(15) . . . . ? C9 C8 N1 C2 0.45(16) . . . . ? C7 C8 N1 C1 -0.3(3) . . . . ? C9 C8 N1 C1 179.30(14) . . . . ? O1 C13 C14 C15 -55.6(2) . . . . ? C10 C11 C15 C14 134.73(16) . . . . ? C12 C11 C15 C14 -36.59(19) . . . . ? C13 C14 C15 C11 56.95(19) . . . . ? O2 C12 O1 C13 171.75(15) . . . . ? C11 C12 O1 C13 -10.1(2) . . . . ? C14 C13 O1 C12 32.1(2) . . . . ? _audit_block_code C16H17NO2_rv414_mayr _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C16 H17 N O2' _chemical_formula_sum 'C16 H17 N O2' _chemical_formula_weight 255.312 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 4 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.31487(14) _exptl_crystal_F_000 544