data_global #=================================================================== # 1. X-Ray Structure Determination _publ_author_name 'Dr. Arkady M. Ellern' _publ_author_address ; 1711 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; _publ_contact_author_phone '+1-515-2947956' _publ_contact_author_fax '+1-515-2945717' _publ_contact_author_email 'ellern@iastate.edu' _publ_contact_letter ; This X-Ray structure Determination has been done in Molecular Structure Lab of Chemistry Department of Iowa State University by Dr. Arkady Ellern. This CIF file has been checked with PLATON software and it is ready for publication. All A-Alerts (if any) are answered in this CIF file, HOWEVER, IT SHOULD BE MODIFIED BEFORE SUBMISSION AS THE ONLY AUTHOR NAME LISTED IS MY NAME as the person who has done X-Ray analysis. All publications arising from this report MUST either 1) include Dr. Arkady Ellern as a coauthor OR 2) acknowledge Dr. Arkady Ellern and the Molecular Structure Laboratory of Iowa State University. Should you have any questions, please, do not hesitate to contact me Sincerely, Dr. Arkady Ellern #=================================================================== ; _audit_creation_method 'APEX2 v2009.11-0' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _audit_creation_method 'APEX2 v2009.11-0' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H17 N' _chemical_formula_iupac ? _chemical_formula_weight 319.39 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 9.6169(5) _cell_length_b 12.7831(9) _cell_length_c 13.5263(9) _cell_angle_alpha 90 _cell_angle_beta 90.225(2) _cell_angle_gamma 90 _cell_volume 1662.8(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6149 _cell_measurement_theta_min 2.1916 _cell_measurement_theta_max 28.2177 _cell_measurement_temperature 173.(2) _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.99 _exptl_special_details ; A X-ray quality crystal was selected under ambient conditions and covered with PARATONE oil The crystal was mounted and centered in the X-ray beam by using a video camera.The crystal evaluation and data collection were performed on APEX-2 CCD diffractometer with the detector to crystal distance of 5cm. The initial cell constants were obtained from three series of OMEGA scans at different starting angles. Each series consisted of 30 frames collected at intervals of 0.3 in a 10 range about OMEGA with the exposure time of 10 seconds per frame. The obtained reflections were successfully indexed by an automated indexing routine built to APEX2 program package. The final cell constants were calculated from a set of strong reflections from the actual data collection. The data were collected using the full sphere routine by collecting four sets of frames with 0.3 scans in \w with an exposure time 10 sec per frame. This dataset was corrected for Lorentz and polarization effects. The absorption correction was based on a fit of a spherical harmonic function to the empirical transmission surface as sampled by multiple equivalent measurements using SADABS software. ; _diffrn_ambient_temperature 173.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source ? _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ' BRUKER APEX2 CCD Diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 19131 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _refine_special_details ; The systematic absences in the diffraction data were consistent for the stated space group. The position of almost all non-hydrogen atoms were found by direct methods. The remaining atoms were located in an alternating series of least-squares cycles on difference Fourier maps. All non-hydrogen atoms were refined in full-matrix anisotropic approximation. All hydrogen atoms were placed in the structure factor calculation at idealized positions and were allowed to ride on the neighboring atoms with relative isotropic displacement coefficients. Final results were tested with CHECKCIF routine and all A-warnings (if any) were addressed on the very top of this file. ; _reflns_number_total 4130 _reflns_number_gt 3352 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_gt 0.1309 _refine_ls_wR_factor_ref 0.1429 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_number_reflns 4130 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.9302P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.464 _refine_diff_density_min -0.339 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'APEX2 Suite (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.66A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.66A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHELL (Bruker AXS, 2007)' _computing_publication_material 'APEX2 Suite (Bruker AXS, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.11876(12) 0.07738(9) 0.30689(9) 0.0264(2) Uani d . 1 . . C C1 0.15223(16) 0.09407(13) -0.05017(12) 0.0374(4) Uani d . 1 . . H H1 0.1663 0.0615 -0.1125 0.045 Uiso calc R 1 . . C C2 0.15239(14) 0.03433(12) 0.03435(12) 0.0347(2) Uani d . 1 . . H H2 0.1664 -0.0391 0.0302 0.042 Uiso calc R 1 . . C C3 0.13182(13) 0.08174(12) 0.12703(11) 0.0286(2) Uani d . 1 . . C C4 0.11525(13) 0.19113(12) 0.13224(10) 0.0282(2) Uani d . 1 . . C C5 0.10470(14) 0.24178(12) 0.22787(11) 0.0299(2) Uani d . 1 . . H H5 0.0931 0.3155 0.2307 0.036 Uiso calc R 1 . . C C6 0.11083(13) 0.18722(12) 0.31239(11) 0.0282(2) Uani d . 1 . . C C7 0.11230(14) 0.23770(12) 0.41153(10) 0.0292(2) Uani d . 1 . . C C8 0.00966(14) 0.30917(12) 0.43744(11) 0.0329(2) Uani d . 1 . . H H8 -0.0625 0.325 0.3917 0.04 Uiso calc R 1 . . C C9 0.01127(14) 0.35781(12) 0.52944(11) 0.0313(2) Uani d . 1 . . H H9 -0.0593 0.4069 0.5454 0.038 Uiso calc R 1 . . C C10 0.11519(13) 0.33538(11) 0.59849(10) 0.0250(2) Uani d . 1 . . C C11 0.11524(13) 0.38596(11) 0.69719(10) 0.0244(2) Uani d . 1 . . C C12 -0.00996(14) 0.41351(12) 0.74249(11) 0.0290(2) Uani d . 1 . . H H12 -0.0956 0.3964 0.7111 0.035 Uiso calc R 1 . . C C13 -0.01102(16) 0.46534(12) 0.83246(11) 0.0319(2) Uani d . 1 . . H H13 -0.0969 0.484 0.8621 0.038 Uiso calc R 1 . . C C14 0.11271(18) 0.48986(12) 0.87910(12) 0.0369(4) Uani d . 1 . . H H14 0.1121 0.5259 0.9405 0.044 Uiso calc R 1 . . C C15 0.12629(13) 0.02267(12) 0.21781(11) 0.0289(2) Uani d . 1 . . C C16 0.12299(16) -0.08260(12) 0.24054(12) 0.0371(4) Uani d . 1 . . H H16 0.1271 -0.1388 0.1947 0.044 Uiso calc R 1 . . C C17 0.11245(16) -0.09166(12) 0.34422(13) 0.0389(4) Uani d . 1 . . H H17 0.1076 -0.1553 0.3804 0.047 Uiso calc R 1 . . C C18 0.11042(14) 0.00703(12) 0.38388(12) 0.0316(2) Uani d . 1 . . H H18 0.1044 0.0239 0.4521 0.038 Uiso calc R 1 . . C C19 0.11494(16) 0.24996(12) 0.04481(11) 0.0331(2) Uani d . 1 . . H H19 0.1031 0.3237 0.0478 0.04 Uiso calc R 1 . . C C20 0.13166(16) 0.20174(13) -0.04537(11) 0.0364(4) Uani d . 1 . . H H20 0.1291 0.242 -0.1044 0.044 Uiso calc R 1 . . C C21 0.21826(14) 0.21764(12) 0.47896(11) 0.0330(2) Uani d . 1 . . H H21 0.291 0.1709 0.4617 0.04 Uiso calc R 1 . . C C22 0.21911(14) 0.26500(12) 0.57110(11) 0.0297(2) Uani d . 1 . . H H22 0.2918 0.2493 0.6165 0.036 Uiso calc R 1 . . C C23 0.23783(17) 0.46179(14) 0.83609(12) 0.0401(4) Uani d . 1 . . H H23 0.323 0.4782 0.8684 0.048 Uiso calc R 1 . . C C24 0.23915(14) 0.40992(12) 0.74611(11) 0.0315(2) Uani d . 1 . . H H24 0.3254 0.3905 0.7174 0.038 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0209(5) 0.0256(5) 0.0327(5) 0.0006(4) 0.0004(4) 0.0029(5) C1 0.0297(7) 0.0532(10) 0.0295(7) -0.0077(7) 0.0018(5) -0.0140(7) C2 0.0257(7) 0.0398(8) 0.0387(8) -0.0035(5) 0.0005(5) -0.0107(7) C3 0.0181(5) 0.0366(8) 0.0309(7) -0.0028(5) -0.0014(5) -0.0025(5) C4 0.0217(5) 0.0367(8) 0.0261(7) -0.0032(5) -0.0012(5) -0.0033(5) C5 0.0304(7) 0.0285(7) 0.0307(7) 0.0004(5) -0.0005(5) -0.0009(5) C6 0.0237(5) 0.0291(7) 0.0319(7) 0.0010(5) 0.0007(5) -0.0012(5) C7 0.0264(7) 0.0362(8) 0.0251(7) 0.0001(5) 0.0016(5) -0.0003(5) C8 0.0271(7) 0.0449(9) 0.0267(7) 0.0059(5) -0.0034(5) 0.0003(5) C9 0.0250(7) 0.0396(8) 0.0294(7) 0.0075(5) -0.0004(5) 0.0004(5) C10 0.0222(5) 0.0293(7) 0.0235(5) -0.0005(5) 0.0009(5) 0.0014(5) C11 0.0242(5) 0.0250(5) 0.0239(5) 0.0002(5) 0.0008(5) 0.0017(5) C12 0.0231(5) 0.0348(8) 0.0292(7) 0.0005(5) 0.0003(5) -0.0016(5) C13 0.0303(7) 0.0333(8) 0.0322(7) -0.0002(5) 0.0059(5) -0.0038(5) C14 0.0406(8) 0.0397(9) 0.0305(7) -0.0064(7) 0.0024(5) -0.0094(5) C15 0.0196(5) 0.0324(7) 0.0347(7) 0.0001(5) -0.0022(5) -0.0024(5) C16 0.0306(7) 0.0296(8) 0.0509(10) 0.0014(5) -0.0056(7) -0.0046(7) C17 0.0302(8) 0.0294(8) 0.0572(10) -0.0016(5) -0.0068(7) 0.0115(7) C18 0.0244(7) 0.0358(8) 0.0345(8) -0.0012(5) -0.0001(5) 0.0088(5) C19 0.0311(7) 0.0378(8) 0.0302(7) -0.0034(5) -0.0009(5) -0.0020(5) C20 0.0313(7) 0.0505(10) 0.0274(7) -0.0075(7) -0.0004(5) -0.0016(7) C21 0.0285(7) 0.0391(8) 0.0313(7) 0.0068(5) 0.0010(5) -0.0040(5) C22 0.0251(7) 0.0365(8) 0.0275(7) 0.0042(5) -0.0023(5) -0.0005(5) C23 0.0303(8) 0.0551(11) 0.0348(8) -0.0097(7) -0.0041(5) -0.0091(7) C24 0.0232(5) 0.0403(8) 0.0310(7) -0.0020(5) 0.0017(5) -0.0021(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C18 . 1.3785(18) ? N1 C15 . 1.395(2) ? N1 C6 . 1.408(2) ? C1 C2 . 1.375(2) ? C1 C20 . 1.392(3) ? C1 H1 . 0.95 ? C2 C3 . 1.407(2) ? C2 H2 . 0.95 ? C3 C4 . 1.409(2) ? C3 C15 . 1.443(2) ? C4 C19 . 1.401(2) ? C4 C5 . 1.451(2) ? C5 C6 . 1.340(2) ? C5 H5 . 0.95 ? C6 C7 . 1.488(2) ? C7 C21 . 1.389(2) ? C7 C8 . 1.391(2) ? C8 C9 . 1.391(2) ? C8 H8 . 0.95 ? C9 C10 . 1.395(2) ? C9 H9 . 0.95 ? C10 C22 . 1.396(2) ? C10 C11 . 1.483(2) ? C11 C24 . 1.395(2) ? C11 C12 . 1.398(2) ? C12 C13 . 1.386(2) ? C12 H12 . 0.95 ? C13 C14 . 1.381(2) ? C13 H13 . 0.95 ? C14 C23 . 1.386(2) ? C14 H14 . 0.95 ? C15 C16 . 1.381(2) ? C16 C17 . 1.411(3) ? C16 H16 . 0.95 ? C17 C18 . 1.371(2) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? C19 C20 . 1.377(2) ? C19 H19 . 0.95 ? C20 H20 . 0.95 ? C21 C22 . 1.386(2) ? C21 H21 . 0.95 ? C22 H22 . 0.95 ? C23 C24 . 1.386(2) ? C23 H23 . 0.95 ? C24 H24 . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C18 N1 C15 . . 109.20(13) ? C18 N1 C6 . . 127.39(13) ? C15 N1 C6 . . 123.26(12) ? C2 C1 C20 . . 120.68(14) ? C2 C1 H1 . . 119.7 ? C20 C1 H1 . . 119.7 ? C1 C2 C3 . . 120.13(15) ? C1 C2 H2 . . 119.9 ? C3 C2 H2 . . 119.9 ? C2 C3 C4 . . 119.23(14) ? C2 C3 C15 . . 122.60(15) ? C4 C3 C15 . . 118.17(13) ? C19 C4 C3 . . 119.35(13) ? C19 C4 C5 . . 120.87(14) ? C3 C4 C5 . . 119.73(13) ? C6 C5 C4 . . 121.70(14) ? C6 C5 H5 . . 119.2 ? C4 C5 H5 . . 119.2 ? C5 C6 N1 . . 118.43(13) ? C5 C6 C7 . . 122.90(14) ? N1 C6 C7 . . 118.66(13) ? C21 C7 C8 . . 118.39(13) ? C21 C7 C6 . . 121.07(13) ? C8 C7 C6 . . 120.51(13) ? C7 C8 C9 . . 120.90(13) ? C7 C8 H8 . . 119.5 ? C9 C8 H8 . . 119.5 ? C8 C9 C10 . . 120.83(13) ? C8 C9 H9 . . 119.6 ? C10 C9 H9 . . 119.6 ? C9 C10 C22 . . 117.81(13) ? C9 C10 C11 . . 120.71(12) ? C22 C10 C11 . . 121.48(12) ? C24 C11 C12 . . 118.19(13) ? C24 C11 C10 . . 121.33(12) ? C12 C11 C10 . . 120.46(12) ? C13 C12 C11 . . 120.97(13) ? C13 C12 H12 . . 119.5 ? C11 C12 H12 . . 119.5 ? C14 C13 C12 . . 120.04(14) ? C14 C13 H13 . . 120.0 ? C12 C13 H13 . . 120.0 ? C13 C14 C23 . . 119.84(14) ? C13 C14 H14 . . 120.1 ? C23 C14 H14 . . 120.1 ? C16 C15 N1 . . 107.15(14) ? C16 C15 C3 . . 134.47(15) ? N1 C15 C3 . . 118.36(13) ? C15 C16 C17 . . 107.64(14) ? C15 C16 H16 . . 126.2 ? C17 C16 H16 . . 126.2 ? C18 C17 C16 . . 108.33(14) ? C18 C17 H17 . . 125.8 ? C16 C17 H17 . . 125.8 ? C17 C18 N1 . . 107.68(14) ? C17 C18 H18 . . 126.2 ? N1 C18 H18 . . 126.2 ? C20 C19 C4 . . 120.50(15) ? C20 C19 H19 . . 119.7 ? C4 C19 H19 . . 119.7 ? C19 C20 C1 . . 120.07(15) ? C19 C20 H20 . . 120.0 ? C1 C20 H20 . . 120.0 ? C22 C21 C7 . . 120.78(14) ? C22 C21 H21 . . 119.6 ? C7 C21 H21 . . 119.6 ? C21 C22 C10 . . 121.24(13) ? C21 C22 H22 . . 119.4 ? C10 C22 H22 . . 119.4 ? C14 C23 C24 . . 120.23(14) ? C14 C23 H23 . . 119.9 ? C24 C23 H23 . . 119.9 ? C23 C24 C11 . . 120.72(14) ? C23 C24 H24 . . 119.6 ? C11 C24 H24 . . 119.6 ?