data_global
#==============================================================================
# SUBMISSION DETAILS
_publ_contact_author_name 'Viktor O. Iaroshenko, Peter Langer'
_publ_contact_author_address
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
_publ_contact_author_email
;
iva108@googlemail.com; peter.langer@uni-rostock.de
;
_publ_contact_author_fax '+49 (0)381/498-6412'
_publ_contact_author_phone '+49 (0)381/498-6410'
_publ_requested_journal 'J. Org. Chem.'
#==============================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
;
Regioselective and Guided C-H Activation of 4-Nitropyrazoles
;
_publ_section_title_footnote .
loop_
_publ_author_name
_publ_author_address
'Viktor O. Iaroshenko'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
National Taras Shevchenko University
62 Volodymyrska st.
Kyiv-33, 01033
Ukraine
;
'Ashot Gevorgyan'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Olena Davydova'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Alexander Villinger'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Anorganische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Peter Langer'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
#=============================================================================
data_is_ag407
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H11 N3 O3'
_chemical_formula_sum
'C12 H11 N3 O3'
_chemical_formula_weight 245.24
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'
#==============================================================================
# CRYSTAL DATA
_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'
_cell_length_a 7.2879(12)
_cell_length_b 18.828(3)
_cell_length_c 8.5038(14)
_cell_angle_alpha 90.00
_cell_angle_beta 93.045(6)
_cell_angle_gamma 90.00
_cell_volume 1165.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 2602
_cell_measurement_theta_min 5.262
_cell_measurement_theta_max 49.294
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.398
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 512
_exptl_absorpt_coefficient_mu 0.103
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9726
_exptl_absorpt_correction_T_max 0.9948
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16039
_diffrn_reflns_av_R_equivalents 0.0486
_diffrn_reflns_av_sigmaI/netI 0.0620
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 3.00
_diffrn_reflns_theta_max 30.00
_reflns_number_total 3387
_reflns_number_gt 1997
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material 'SHELXL-97'
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.3514P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3387
_refine_ls_number_parameters 165
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1153
_refine_ls_R_factor_gt 0.0564
_refine_ls_wR_factor_ref 0.1387
_refine_ls_wR_factor_gt 0.1127
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_restrained_S_all 1.018
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.2591(2) 0.53992(7) 0.45729(16) 0.0246(3) Uani 1 1 d . . .
N2 N 0.2021(2) 0.47108(8) 0.46450(17) 0.0294(4) Uani 1 1 d . . .
N3 N 0.2912(2) 0.51619(8) 0.87189(17) 0.0326(4) Uani 1 1 d . . .
O1 O 0.2545(3) 0.46209(8) 0.94378(17) 0.0656(6) Uani 1 1 d . . .
O2 O 0.3397(2) 0.57128(7) 0.93688(15) 0.0479(4) Uani 1 1 d . . .
O3 O 0.8865(2) 0.78835(7) 0.7930(2) 0.0513(4) Uani 1 1 d . . .
C1 C 0.3058(2) 0.56855(9) 0.59939(18) 0.0214(4) Uani 1 1 d . . .
C2 C 0.2745(3) 0.51347(9) 0.70454(19) 0.0239(4) Uani 1 1 d . . .
C3 C 0.2118(3) 0.45513(9) 0.6156(2) 0.0283(4) Uani 1 1 d . . .
H3 H 0.1806 0.4103 0.6581 0.034 Uiso 1 1 calc R . .
C4 C 0.2695(3) 0.57240(11) 0.3016(2) 0.0367(5) Uani 1 1 d . . .
H4A H 0.1625 0.6031 0.2805 0.055 Uiso 1 1 calc R . .
H4B H 0.2709 0.5351 0.2214 0.055 Uiso 1 1 calc R . .
H4C H 0.3821 0.6007 0.2988 0.055 Uiso 1 1 calc R . .
C5 C 0.3816(2) 0.64095(9) 0.61826(19) 0.0228(4) Uani 1 1 d . . .
C6 C 0.5542(2) 0.65057(9) 0.69375(19) 0.0225(4) Uani 1 1 d . . .
H6 H 0.6178 0.6109 0.7391 0.027 Uiso 1 1 calc R . .
C7 C 0.6347(2) 0.71764(9) 0.70355(19) 0.0240(4) Uani 1 1 d . . .
C8 C 0.5405(3) 0.77547(9) 0.6380(2) 0.0314(4) Uani 1 1 d . . .
H8 H 0.5947 0.8213 0.6432 0.038 Uiso 1 1 calc R . .
C9 C 0.3677(3) 0.76639(10) 0.5652(2) 0.0379(5) Uani 1 1 d . . .
H9 H 0.3030 0.8063 0.5222 0.045 Uiso 1 1 calc R . .
C10 C 0.2884(3) 0.69961(9) 0.5545(2) 0.0316(4) Uani 1 1 d . . .
H10 H 0.1701 0.6938 0.5036 0.038 Uiso 1 1 calc R . .
C11 C 0.8225(3) 0.72882(10) 0.7799(2) 0.0309(4) Uani 1 1 d . . .
C12 C 0.9297(3) 0.66558(11) 0.8383(3) 0.0440(6) Uani 1 1 d . . .
H12A H 1.0582 0.6792 0.8608 0.066 Uiso 1 1 calc R . .
H12B H 0.9234 0.6283 0.7577 0.066 Uiso 1 1 calc R . .
H12C H 0.8779 0.6477 0.9347 0.066 Uiso 1 1 calc R . .
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 0.0288(8) 0.0258(8) 0.0190(7) -0.0021(5) 0.0004(6) -0.0009(7)
N2 0.0324(9) 0.0251(8) 0.0305(8) -0.0072(6) -0.0008(7) -0.0010(7)
N3 0.0514(11) 0.0226(8) 0.0239(8) 0.0041(6) 0.0019(7) -0.0002(8)
O1 0.1296(17) 0.0349(9) 0.0319(8) 0.0126(6) 0.0012(9) -0.0191(10)
O2 0.0904(13) 0.0321(8) 0.0208(7) -0.0034(6) 0.0006(7) -0.0116(8)
O3 0.0421(9) 0.0262(8) 0.0839(12) -0.0088(7) -0.0135(8) -0.0063(7)
C1 0.0227(9) 0.0222(8) 0.0193(8) -0.0015(6) 0.0003(6) 0.0017(8)
C2 0.0294(10) 0.0219(8) 0.0201(8) 0.0007(6) -0.0009(7) 0.0017(8)
C3 0.0322(10) 0.0218(9) 0.0309(10) 0.0003(7) 0.0007(8) 0.0014(8)
C4 0.0473(13) 0.0455(12) 0.0174(9) 0.0018(8) 0.0016(8) -0.0021(11)
C5 0.0281(10) 0.0203(8) 0.0202(8) 0.0008(6) 0.0020(7) 0.0001(8)
C6 0.0273(9) 0.0188(8) 0.0216(8) 0.0001(6) 0.0013(7) 0.0023(8)
C7 0.0269(10) 0.0205(8) 0.0247(9) -0.0025(6) 0.0021(7) 0.0007(8)
C8 0.0388(12) 0.0193(9) 0.0359(10) 0.0021(7) -0.0003(9) -0.0033(9)
C9 0.0439(13) 0.0224(9) 0.0459(12) 0.0103(8) -0.0115(10) 0.0020(9)
C10 0.0333(11) 0.0275(10) 0.0330(10) 0.0048(7) -0.0087(8) 0.0011(9)
C11 0.0304(11) 0.0254(9) 0.0366(10) -0.0053(7) 0.0000(8) -0.0013(9)
C12 0.0342(12) 0.0314(11) 0.0645(15) -0.0013(10) -0.0145(11) -0.0009(10)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.350(2) . ?
N1 N2 1.3636(19) . ?
N1 C4 1.464(2) . ?
N2 C3 1.318(2) . ?
N3 O2 1.2186(19) . ?
N3 O1 1.2248(19) . ?
N3 C2 1.423(2) . ?
O3 C11 1.217(2) . ?
C1 C2 1.396(2) . ?
C1 C5 1.476(2) . ?
C2 C3 1.397(2) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.391(2) . ?
C5 C6 1.394(3) . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C11 1.498(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.495(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 N1 N2 113.71(14) . . ?
C1 N1 C4 128.32(15) . . ?
N2 N1 C4 117.92(14) . . ?
C3 N2 N1 105.05(14) . . ?
O2 N3 O1 123.17(16) . . ?
O2 N3 C2 119.44(14) . . ?
O1 N3 C2 117.39(15) . . ?
N1 C1 C2 103.58(14) . . ?
N1 C1 C5 122.74(14) . . ?
C2 C1 C5 133.57(15) . . ?
C1 C2 C3 107.30(15) . . ?
C1 C2 N3 127.29(15) . . ?
C3 C2 N3 125.30(15) . . ?
N2 C3 C2 110.35(15) . . ?
N2 C3 H3 124.8 . . ?
C2 C3 H3 124.8 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 119.10(16) . . ?
C10 C5 C1 121.24(16) . . ?
C6 C5 C1 119.56(15) . . ?
C7 C6 C5 120.83(16) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 119.29(17) . . ?
C8 C7 C11 119.00(16) . . ?
C6 C7 C11 121.70(16) . . ?
C9 C8 C7 120.11(17) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.54(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.12(18) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O3 C11 C12 120.77(18) . . ?
O3 C11 C7 120.42(17) . . ?
C12 C11 C7 118.80(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
C1 N1 N2 C3 0.2(2) . . . . ?
C4 N1 N2 C3 177.91(16) . . . . ?
N2 N1 C1 C2 -0.4(2) . . . . ?
C4 N1 C1 C2 -177.80(17) . . . . ?
N2 N1 C1 C5 176.31(15) . . . . ?
C4 N1 C1 C5 -1.1(3) . . . . ?
N1 C1 C2 C3 0.4(2) . . . . ?
C5 C1 C2 C3 -175.76(18) . . . . ?
N1 C1 C2 N3 -175.97(17) . . . . ?
C5 C1 C2 N3 7.9(3) . . . . ?
O2 N3 C2 C1 -0.9(3) . . . . ?
O1 N3 C2 C1 178.8(2) . . . . ?
O2 N3 C2 C3 -176.61(19) . . . . ?
O1 N3 C2 C3 3.1(3) . . . . ?
N1 N2 C3 C2 0.1(2) . . . . ?
C1 C2 C3 N2 -0.3(2) . . . . ?
N3 C2 C3 N2 176.15(17) . . . . ?
N1 C1 C5 C10 55.6(2) . . . . ?
C2 C1 C5 C10 -128.9(2) . . . . ?
N1 C1 C5 C6 -120.90(18) . . . . ?
C2 C1 C5 C6 54.7(3) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C1 C5 C6 C7 175.48(14) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 C11 -178.14(16) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C11 C7 C8 C9 179.26(18) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C6 C5 C10 C9 0.6(3) . . . . ?
C1 C5 C10 C9 -175.90(17) . . . . ?
C8 C7 C11 O3 4.6(3) . . . . ?
C6 C7 C11 O3 -176.81(17) . . . . ?
C8 C7 C11 C12 -174.96(18) . . . . ?
C6 C7 C11 C12 3.6(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.310
_refine_diff_density_min -0.297
_refine_diff_density_rms 0.053
#=============================================================================
data_is_ag421
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H14 N4 O2'
_chemical_formula_sum
'C16 H14 N4 O2'
_chemical_formula_weight 294.31
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'
#==============================================================================
# CRYSTAL DATA
_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'
_cell_length_a 11.8416(4)
_cell_length_b 6.0888(2)
_cell_length_c 21.1714(7)
_cell_angle_alpha 90.00
_cell_angle_beta 105.700(2)
_cell_angle_gamma 90.00
_cell_volume 1469.53(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 7119
_cell_measurement_theta_min 4.542
_cell_measurement_theta_max 65.148
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.70
_exptl_crystal_size_mid 0.46
_exptl_crystal_size_min 0.32
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.330
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9387
_exptl_absorpt_correction_T_max 0.9713
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 19154
_diffrn_reflns_av_R_equivalents 0.0369
_diffrn_reflns_av_sigmaI/netI 0.0298
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 1.80
_diffrn_reflns_theta_max 31.00
_reflns_number_total 4681
_reflns_number_gt 3808
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material 'SHELXL-97'
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.3395P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4681
_refine_ls_number_parameters 200
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0575
_refine_ls_R_factor_gt 0.0460
_refine_ls_wR_factor_ref 0.1310
_refine_ls_wR_factor_gt 0.1218
_refine_ls_goodness_of_fit_ref 1.038
_refine_ls_restrained_S_all 1.038
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 1.19520(8) 0.17122(16) 0.18509(4) 0.0280(2) Uani 1 1 d . . .
N2 N 1.01088(10) 0.80900(16) 0.07530(5) 0.0341(2) Uani 1 1 d . . .
N3 N 0.90686(8) 0.24346(16) 0.20132(4) 0.02601(19) Uani 1 1 d . . .
N4 N 0.94711(9) 0.09215(18) 0.24961(5) 0.0331(2) Uani 1 1 d . . .
O1 O 1.26975(8) 0.04347(19) 0.21651(5) 0.0483(3) Uani 1 1 d . . .
O2 O 1.21153(7) 0.29227(15) 0.14200(4) 0.0335(2) Uani 1 1 d . . .
C1 C 0.98759(8) 0.30104(16) 0.17002(5) 0.02151(19) Uani 1 1 d . . .
C2 C 1.08598(9) 0.17857(17) 0.20068(5) 0.0243(2) Uani 1 1 d . . .
C3 C 1.05646(10) 0.0529(2) 0.24929(5) 0.0313(2) Uani 1 1 d . . .
H3 H 1.1078 -0.0463 0.2779 0.038 Uiso 1 1 calc R . .
C4 C 0.96361(9) 0.46208(16) 0.11623(5) 0.02192(19) Uani 1 1 d . . .
C5 C 1.02941(10) 0.65445(17) 0.12160(5) 0.0287(2) Uani 1 1 d . . .
H5 H 1.0910 0.6767 0.1605 0.034 Uiso 1 1 calc R . .
C6 C 0.92415(11) 0.77319(19) 0.02059(6) 0.0312(2) Uani 1 1 d . . .
H6 H 0.9099 0.8813 -0.0130 0.037 Uiso 1 1 calc R . .
C7 C 0.85447(10) 0.5876(2) 0.01048(5) 0.0304(2) Uani 1 1 d . . .
H7 H 0.7939 0.5694 -0.0291 0.036 Uiso 1 1 calc R . .
C8 C 0.87438(9) 0.42859(18) 0.05901(5) 0.0266(2) Uani 1 1 d . . .
H8 H 0.8280 0.2991 0.0533 0.032 Uiso 1 1 calc R . .
C9 C 0.78662(9) 0.32013(19) 0.19036(5) 0.0279(2) Uani 1 1 d . . .
H9A H 0.7777 0.4609 0.1661 0.033 Uiso 1 1 calc R . .
H9B H 0.7715 0.3488 0.2334 0.033 Uiso 1 1 calc R . .
C10 C 0.69577(9) 0.15977(18) 0.15241(5) 0.0263(2) Uani 1 1 d . . .
C11 C 0.72227(10) -0.03064(19) 0.12342(6) 0.0314(2) Uani 1 1 d . . .
H11 H 0.8017 -0.0661 0.1266 0.038 Uiso 1 1 calc R . .
C12 C 0.63322(11) -0.1699(2) 0.08971(6) 0.0354(3) Uani 1 1 d . . .
H12 H 0.6529 -0.2990 0.0698 0.042 Uiso 1 1 calc R . .
C13 C 0.51642(10) -0.1245(2) 0.08450(6) 0.0362(3) Uani 1 1 d . . .
C14 C 0.49081(11) 0.0670(3) 0.11279(8) 0.0515(4) Uani 1 1 d . . .
H14 H 0.4113 0.1028 0.1094 0.062 Uiso 1 1 calc R . .
C15 C 0.57873(11) 0.2076(3) 0.14601(8) 0.0462(4) Uani 1 1 d . . .
H15 H 0.5586 0.3388 0.1647 0.055 Uiso 1 1 calc R . .
C16 C 0.41991(13) -0.2759(3) 0.04814(9) 0.0529(4) Uani 1 1 d . . .
H16A H 0.3500 -0.2529 0.0637 0.079 Uiso 1 1 calc R . .
H16B H 0.4459 -0.4287 0.0561 0.079 Uiso 1 1 calc R . .
H16C H 0.4010 -0.2446 0.0010 0.079 Uiso 1 1 calc R . .
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 0.0242(4) 0.0325(5) 0.0253(4) 0.0045(3) 0.0034(3) 0.0008(3)
N2 0.0427(6) 0.0244(4) 0.0336(5) 0.0045(4) 0.0076(4) -0.0058(4)
N3 0.0260(4) 0.0281(4) 0.0238(4) 0.0059(3) 0.0064(3) 0.0000(3)
N4 0.0331(5) 0.0381(5) 0.0287(4) 0.0138(4) 0.0093(4) 0.0026(4)
O1 0.0318(4) 0.0600(6) 0.0534(6) 0.0281(5) 0.0122(4) 0.0179(4)
O2 0.0290(4) 0.0429(5) 0.0292(4) 0.0100(3) 0.0086(3) -0.0007(3)
C1 0.0232(4) 0.0211(4) 0.0186(4) -0.0001(3) 0.0030(3) -0.0032(3)
C2 0.0237(4) 0.0261(5) 0.0214(4) 0.0026(4) 0.0034(3) -0.0014(4)
C3 0.0306(5) 0.0352(6) 0.0267(5) 0.0111(4) 0.0056(4) 0.0022(4)
C4 0.0235(4) 0.0212(4) 0.0206(4) 0.0020(3) 0.0051(3) -0.0001(3)
C5 0.0334(5) 0.0234(5) 0.0267(5) 0.0004(4) 0.0035(4) -0.0052(4)
C6 0.0361(6) 0.0278(5) 0.0300(5) 0.0096(4) 0.0096(4) 0.0021(4)
C7 0.0269(5) 0.0372(6) 0.0247(5) 0.0082(4) 0.0028(4) -0.0013(4)
C8 0.0254(4) 0.0287(5) 0.0239(4) 0.0039(4) 0.0033(4) -0.0054(4)
C9 0.0265(5) 0.0289(5) 0.0297(5) 0.0005(4) 0.0101(4) 0.0013(4)
C10 0.0249(5) 0.0303(5) 0.0256(5) 0.0004(4) 0.0102(4) 0.0015(4)
C11 0.0260(5) 0.0281(5) 0.0411(6) -0.0005(5) 0.0108(4) 0.0043(4)
C12 0.0343(6) 0.0273(5) 0.0445(7) -0.0048(5) 0.0106(5) 0.0030(4)
C13 0.0298(5) 0.0378(6) 0.0401(6) -0.0043(5) 0.0078(5) -0.0028(5)
C14 0.0245(5) 0.0644(10) 0.0666(9) -0.0261(8) 0.0139(6) -0.0002(6)
C15 0.0282(6) 0.0540(8) 0.0587(8) -0.0265(7) 0.0159(6) 0.0021(5)
C16 0.0377(7) 0.0505(8) 0.0650(10) -0.0126(8) 0.0046(7) -0.0102(6)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 O2 1.2283(12) . ?
N1 O1 1.2284(12) . ?
N1 C2 1.4193(14) . ?
N2 C5 1.3334(14) . ?
N2 C6 1.3417(16) . ?
N3 C1 1.3486(13) . ?
N3 N4 1.3629(12) . ?
N3 C9 1.4561(14) . ?
N4 C3 1.3185(15) . ?
C1 C2 1.3877(14) . ?
C1 C4 1.4710(13) . ?
C2 C3 1.4006(14) . ?
C3 H3 0.9500 . ?
C4 C8 1.3904(13) . ?
C4 C5 1.3943(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3811(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3848(15) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.5128(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.3866(16) . ?
C10 C11 1.3868(16) . ?
C11 C12 1.3903(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3852(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3814(19) . ?
C13 C16 1.5076(18) . ?
C14 C15 1.3840(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
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
O2 N1 O1 123.21(10) . . ?
O2 N1 C2 119.36(9) . . ?
O1 N1 C2 117.43(9) . . ?
C5 N2 C6 117.08(10) . . ?
C1 N3 N4 113.19(9) . . ?
C1 N3 C9 129.12(9) . . ?
N4 N3 C9 117.69(9) . . ?
C3 N4 N3 105.26(9) . . ?
N3 C1 C2 104.33(8) . . ?
N3 C1 C4 122.66(9) . . ?
C2 C1 C4 133.00(9) . . ?
C1 C2 C3 107.00(9) . . ?
C1 C2 N1 127.65(9) . . ?
C3 C2 N1 125.31(9) . . ?
N4 C3 C2 110.21(10) . . ?
N4 C3 H3 124.9 . . ?
C2 C3 H3 124.9 . . ?
C8 C4 C5 118.05(9) . . ?
C8 C4 C1 121.25(9) . . ?
C5 C4 C1 120.69(9) . . ?
N2 C5 C4 123.77(10) . . ?
N2 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N2 C6 C7 123.53(10) . . ?
N2 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
C6 C7 C8 118.85(10) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C4 118.72(10) . . ?
C7 C8 H8 120.6 . . ?
C4 C8 H8 120.6 . . ?
N3 C9 C10 113.70(9) . . ?
N3 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 118.19(11) . . ?
C15 C10 C9 117.69(10) . . ?
C11 C10 C9 124.12(10) . . ?
C10 C11 C12 120.39(10) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 121.44(11) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 117.74(12) . . ?
C14 C13 C16 120.83(12) . . ?
C12 C13 C16 121.42(12) . . ?
C13 C14 C15 121.29(12) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 120.94(12) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
C1 N3 N4 C3 0.26(13) . . . . ?
C9 N3 N4 C3 -179.70(10) . . . . ?
N4 N3 C1 C2 -0.23(12) . . . . ?
C9 N3 C1 C2 179.72(10) . . . . ?
N4 N3 C1 C4 -179.91(9) . . . . ?
C9 N3 C1 C4 0.04(17) . . . . ?
N3 C1 C2 C3 0.11(11) . . . . ?
C4 C1 C2 C3 179.74(11) . . . . ?
N3 C1 C2 N1 177.63(10) . . . . ?
C4 C1 C2 N1 -2.73(18) . . . . ?
O2 N1 C2 C1 4.06(17) . . . . ?
O1 N1 C2 C1 -176.68(11) . . . . ?
O2 N1 C2 C3 -178.84(11) . . . . ?
O1 N1 C2 C3 0.42(17) . . . . ?
N3 N4 C3 C2 -0.18(14) . . . . ?
C1 C2 C3 N4 0.05(13) . . . . ?
N1 C2 C3 N4 -177.55(11) . . . . ?
N3 C1 C4 C8 -59.75(14) . . . . ?
C2 C1 C4 C8 120.67(13) . . . . ?
N3 C1 C4 C5 119.61(12) . . . . ?
C2 C1 C4 C5 -59.97(16) . . . . ?
C6 N2 C5 C4 -0.57(18) . . . . ?
C8 C4 C5 N2 0.71(17) . . . . ?
C1 C4 C5 N2 -178.68(11) . . . . ?
C5 N2 C6 C7 0.25(18) . . . . ?
N2 C6 C7 C8 -0.08(19) . . . . ?
C6 C7 C8 C4 0.21(17) . . . . ?
C5 C4 C8 C7 -0.50(16) . . . . ?
C1 C4 C8 C7 178.89(10) . . . . ?
C1 N3 C9 C10 102.19(13) . . . . ?
N4 N3 C9 C10 -77.86(12) . . . . ?
N3 C9 C10 C15 172.92(11) . . . . ?
N3 C9 C10 C11 -7.48(15) . . . . ?
C15 C10 C11 C12 -0.81(18) . . . . ?
C9 C10 C11 C12 179.60(11) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
C11 C12 C13 C16 -179.79(13) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C16 C13 C14 C15 -179.70(15) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C11 C10 C15 C14 1.3(2) . . . . ?
C9 C10 C15 C14 -179.05(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 31.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.350
_refine_diff_density_min -0.223
_refine_diff_density_rms 0.047
#=============================================================================
data_is_ag459
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H19 N3 O2'
_chemical_formula_sum
'C20 H19 N3 O2'
_chemical_formula_weight 333.38
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'
#==============================================================================
# CRYSTAL DATA
_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'
_cell_length_a 9.6100(3)
_cell_length_b 26.7655(8)
_cell_length_c 6.8056(2)
_cell_angle_alpha 90.00
_cell_angle_beta 105.4850(10)
_cell_angle_gamma 90.00
_cell_volume 1686.97(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 9930
_cell_measurement_theta_min 5.349
_cell_measurement_theta_max 65.170
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.55
_exptl_crystal_size_mid 0.44
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.313
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 704
_exptl_absorpt_coefficient_mu 0.087
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9539
_exptl_absorpt_correction_T_max 0.9820
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 30515
_diffrn_reflns_av_R_equivalents 0.0244
_diffrn_reflns_av_sigmaI/netI 0.0205
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -40
_diffrn_reflns_limit_k_max 30
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 2.67
_diffrn_reflns_theta_max 32.50
_reflns_number_total 6109
_reflns_number_gt 5188
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material 'SHELXL-97'
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.4722P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 6109
_refine_ls_number_parameters 229
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0591
_refine_ls_R_factor_gt 0.0498
_refine_ls_wR_factor_ref 0.1390
_refine_ls_wR_factor_gt 0.1314
_refine_ls_goodness_of_fit_ref 1.071
_refine_ls_restrained_S_all 1.071
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 -0.00944(9) 0.12596(3) 0.67689(13) 0.02204(16) Uani 1 1 d . . .
N2 N -0.13486(9) 0.12142(4) 0.52447(14) 0.02735(19) Uani 1 1 d . . .
N3 N 0.09349(10) 0.19191(4) 0.28733(13) 0.02639(18) Uani 1 1 d . . .
O1 O 0.67694(8) 0.19695(3) 0.92581(11) 0.02639(16) Uani 1 1 d . . .
O2 O 0.54943(8) 0.15257(3) 1.15919(11) 0.02871(18) Uani 1 1 d . . .
C1 C 0.09177(10) 0.15248(3) 0.61294(13) 0.01837(16) Uani 1 1 d . . .
C2 C 0.02696(10) 0.16555(4) 0.40924(14) 0.02172(18) Uani 1 1 d . . .
C3 C -0.11352(11) 0.14500(4) 0.36393(16) 0.0270(2) Uani 1 1 d . . .
H3 H -0.1832 0.1477 0.2357 0.032 Uiso 1 1 calc R . .
C4 C 0.22795(11) 0.20414(4) 0.37363(15) 0.02445(19) Uani 1 1 d . . .
H4 H 0.2772 0.2229 0.2944 0.029 Uiso 1 1 calc R . .
C5 C 0.30711(10) 0.19154(3) 0.57847(13) 0.01871(17) Uani 1 1 d . . .
C6 C 0.45571(10) 0.20382(4) 0.65025(14) 0.02009(17) Uani 1 1 d . . .
H6 H 0.5018 0.2218 0.5649 0.024 Uiso 1 1 calc R . .
C7 C 0.53337(10) 0.18985(3) 0.84262(14) 0.01938(17) Uani 1 1 d . . .
C8 C 0.46210(10) 0.16450(4) 0.97270(13) 0.01975(17) Uani 1 1 d . . .
C9 C 0.31804(10) 0.15278(4) 0.90726(13) 0.01929(17) Uani 1 1 d . . .
H9 H 0.2720 0.1363 0.9965 0.023 Uiso 1 1 calc R . .
C10 C 0.23822(10) 0.16527(3) 0.70681(13) 0.01734(16) Uani 1 1 d . . .
C11 C -0.00641(10) 0.10701(4) 0.87824(15) 0.02384(19) Uani 1 1 d . . .
H11A H -0.1053 0.0965 0.8778 0.029 Uiso 1 1 calc R . .
H11B H 0.0219 0.1346 0.9779 0.029 Uiso 1 1 calc R . .
C12 C 0.09518(10) 0.06348(4) 0.94936(15) 0.02234(18) Uani 1 1 d . . .
C13 C 0.14415(13) 0.03322(4) 0.81603(18) 0.0308(2) Uani 1 1 d . . .
H13 H 0.1120 0.0390 0.6733 0.037 Uiso 1 1 calc R . .
C14 C 0.24029(15) -0.00567(5) 0.8906(2) 0.0365(3) Uani 1 1 d . . .
H14 H 0.2726 -0.0261 0.7976 0.044 Uiso 1 1 calc R . .
C15 C 0.28961(13) -0.01502(4) 1.0983(2) 0.0324(2) Uani 1 1 d . . .
C16 C 0.23713(14) 0.01446(5) 1.23009(19) 0.0332(2) Uani 1 1 d . . .
H16 H 0.2669 0.0079 1.3724 0.040 Uiso 1 1 calc R . .
C17 C 0.14165(13) 0.05340(4) 1.15707(17) 0.0290(2) Uani 1 1 d . . .
H17 H 0.1077 0.0734 1.2501 0.035 Uiso 1 1 calc R . .
C18 C 0.39715(17) -0.05615(6) 1.1792(3) 0.0500(4) Uani 1 1 d . . .
H18A H 0.3595 -0.0879 1.1146 0.075 Uiso 1 1 calc R . .
H18B H 0.4131 -0.0589 1.3271 0.075 Uiso 1 1 calc R . .
H18C H 0.4887 -0.0484 1.1483 0.075 Uiso 1 1 calc R . .
C19 C 0.75643(12) 0.22257(5) 0.80616(18) 0.0314(2) Uani 1 1 d . . .
H19A H 0.7512 0.2036 0.6812 0.047 Uiso 1 1 calc R . .
H19B H 0.8576 0.2258 0.8848 0.047 Uiso 1 1 calc R . .
H19C H 0.7150 0.2559 0.7705 0.047 Uiso 1 1 calc R . .
C20 C 0.49816(12) 0.11597(5) 1.27609(15) 0.0284(2) Uani 1 1 d . . .
H20A H 0.4148 0.1293 1.3162 0.043 Uiso 1 1 calc R . .
H20B H 0.5751 0.1077 1.3984 0.043 Uiso 1 1 calc R . .
H20C H 0.4694 0.0858 1.1938 0.043 Uiso 1 1 calc R . .
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 0.0155(3) 0.0272(4) 0.0210(3) 0.0017(3) 0.0006(3) -0.0005(3)
N2 0.0155(4) 0.0352(5) 0.0268(4) -0.0019(3) -0.0021(3) 0.0002(3)
N3 0.0271(4) 0.0301(5) 0.0179(3) 0.0044(3) -0.0010(3) 0.0015(3)
O1 0.0182(3) 0.0322(4) 0.0257(3) 0.0041(3) 0.0007(3) -0.0073(3)
O2 0.0216(3) 0.0389(4) 0.0196(3) 0.0095(3) -0.0048(3) -0.0073(3)
C1 0.0161(4) 0.0194(4) 0.0172(3) -0.0003(3) 0.0004(3) 0.0017(3)
C2 0.0199(4) 0.0238(4) 0.0180(4) 0.0008(3) -0.0008(3) 0.0034(3)
C3 0.0183(4) 0.0347(5) 0.0228(4) -0.0017(4) -0.0035(3) 0.0026(4)
C4 0.0276(5) 0.0252(5) 0.0182(4) 0.0052(3) 0.0020(3) 0.0003(4)
C5 0.0206(4) 0.0174(4) 0.0163(3) 0.0012(3) 0.0016(3) 0.0003(3)
C6 0.0214(4) 0.0186(4) 0.0193(4) 0.0018(3) 0.0038(3) -0.0016(3)
C7 0.0177(4) 0.0182(4) 0.0202(4) 0.0002(3) 0.0016(3) -0.0024(3)
C8 0.0186(4) 0.0212(4) 0.0164(3) 0.0023(3) -0.0005(3) -0.0011(3)
C9 0.0179(4) 0.0217(4) 0.0162(3) 0.0024(3) 0.0008(3) -0.0013(3)
C10 0.0169(4) 0.0169(4) 0.0160(3) -0.0002(3) 0.0007(3) 0.0007(3)
C11 0.0188(4) 0.0287(5) 0.0242(4) 0.0036(4) 0.0061(3) 0.0019(3)
C12 0.0197(4) 0.0222(4) 0.0256(4) 0.0025(3) 0.0068(3) -0.0017(3)
C13 0.0353(6) 0.0290(5) 0.0297(5) 0.0006(4) 0.0116(4) 0.0032(4)
C14 0.0422(7) 0.0294(6) 0.0441(6) 0.0025(5) 0.0222(5) 0.0082(5)
C15 0.0294(5) 0.0249(5) 0.0474(6) 0.0120(4) 0.0179(5) 0.0041(4)
C16 0.0344(6) 0.0329(6) 0.0333(5) 0.0117(4) 0.0109(4) 0.0064(4)
C17 0.0322(5) 0.0293(5) 0.0268(5) 0.0049(4) 0.0105(4) 0.0053(4)
C18 0.0465(8) 0.0400(7) 0.0710(10) 0.0236(7) 0.0287(7) 0.0194(6)
C19 0.0238(5) 0.0355(6) 0.0356(5) 0.0044(4) 0.0091(4) -0.0070(4)
C20 0.0243(5) 0.0392(6) 0.0200(4) 0.0108(4) 0.0032(3) 0.0007(4)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.3658(12) . ?
N1 N2 1.3696(11) . ?
N1 C11 1.4541(13) . ?
N2 C3 1.3242(15) . ?
N3 C4 1.3102(14) . ?
N3 C2 1.3704(13) . ?
O1 C7 1.3576(11) . ?
O1 C19 1.4314(13) . ?
O2 C8 1.3596(11) . ?
O2 C20 1.4300(13) . ?
C1 C2 1.4040(12) . ?
C1 C10 1.4234(12) . ?
C2 C3 1.4135(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.4386(12) . ?
C4 H4 0.9500 . ?
C5 C10 1.4157(12) . ?
C5 C6 1.4190(13) . ?
C6 C7 1.3745(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.4271(13) . ?
C8 C9 1.3726(13) . ?
C9 C10 1.4151(12) . ?
C9 H9 0.9500 . ?
C11 C12 1.5142(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3889(15) . ?
C12 C17 1.3904(14) . ?
C13 C14 1.3944(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3885(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3865(17) . ?
C15 C18 1.5095(17) . ?
C16 C17 1.3899(16) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C1 N1 N2 111.24(8) . . ?
C1 N1 C11 130.15(8) . . ?
N2 N1 C11 118.36(8) . . ?
C3 N2 N1 106.49(8) . . ?
C4 N3 C2 114.89(8) . . ?
C7 O1 C19 117.85(8) . . ?
C8 O2 C20 117.51(8) . . ?
N1 C1 C2 106.15(8) . . ?
N1 C1 C10 133.23(8) . . ?
C2 C1 C10 120.53(9) . . ?
N3 C2 C1 124.78(9) . . ?
N3 C2 C3 129.87(9) . . ?
C1 C2 C3 105.34(9) . . ?
N2 C3 C2 110.78(9) . . ?
N2 C3 H3 124.6 . . ?
C2 C3 H3 124.6 . . ?
N3 C4 C5 125.37(9) . . ?
N3 C4 H4 117.3 . . ?
C5 C4 H4 117.3 . . ?
C10 C5 C6 119.74(8) . . ?
C10 C5 C4 120.06(8) . . ?
C6 C5 C4 120.16(8) . . ?
C7 C6 C5 120.36(8) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C6 126.30(9) . . ?
O1 C7 C8 114.23(8) . . ?
C6 C7 C8 119.46(8) . . ?
O2 C8 C9 124.54(8) . . ?
O2 C8 C7 114.33(8) . . ?
C9 C8 C7 121.12(8) . . ?
C8 C9 C10 119.93(8) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 119.32(8) . . ?
C9 C10 C1 126.33(8) . . ?
C5 C10 C1 114.32(8) . . ?
N1 C11 C12 114.75(8) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C17 118.56(10) . . ?
C13 C12 C11 122.82(9) . . ?
C17 C12 C11 118.62(9) . . ?
C12 C13 C14 120.30(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 121.21(11) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 118.13(11) . . ?
C16 C15 C18 120.74(12) . . ?
C14 C15 C18 121.12(12) . . ?
C15 C16 C17 121.00(11) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 120.75(10) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
C1 N1 N2 C3 0.00(12) . . . . ?
C11 N1 N2 C3 174.79(9) . . . . ?
N2 N1 C1 C2 0.13(11) . . . . ?
C11 N1 C1 C2 -173.88(10) . . . . ?
N2 N1 C1 C10 -176.50(10) . . . . ?
C11 N1 C1 C10 9.49(18) . . . . ?
C4 N3 C2 C1 1.17(15) . . . . ?
C4 N3 C2 C3 -177.30(11) . . . . ?
N1 C1 C2 N3 -178.98(9) . . . . ?
C10 C1 C2 N3 -1.83(15) . . . . ?
N1 C1 C2 C3 -0.19(11) . . . . ?
C10 C1 C2 C3 176.95(9) . . . . ?
N1 N2 C3 C2 -0.13(12) . . . . ?
N3 C2 C3 N2 178.90(10) . . . . ?
C1 C2 C3 N2 0.20(12) . . . . ?
C2 N3 C4 C5 0.90(16) . . . . ?
N3 C4 C5 C10 -2.32(16) . . . . ?
N3 C4 C5 C6 175.46(10) . . . . ?
C10 C5 C6 C7 0.76(14) . . . . ?
C4 C5 C6 C7 -177.02(9) . . . . ?
C19 O1 C7 C6 1.77(15) . . . . ?
C19 O1 C7 C8 -179.38(9) . . . . ?
C5 C6 C7 O1 176.45(9) . . . . ?
C5 C6 C7 C8 -2.35(14) . . . . ?
C20 O2 C8 C9 15.12(15) . . . . ?
C20 O2 C8 C7 -163.33(9) . . . . ?
O1 C7 C8 O2 1.14(13) . . . . ?
C6 C7 C8 O2 -179.93(9) . . . . ?
O1 C7 C8 C9 -177.37(9) . . . . ?
C6 C7 C8 C9 1.57(15) . . . . ?
O2 C8 C9 C10 -177.50(9) . . . . ?
C7 C8 C9 C10 0.85(15) . . . . ?
C8 C9 C10 C5 -2.44(14) . . . . ?
C8 C9 C10 C1 175.21(9) . . . . ?
C6 C5 C10 C9 1.65(13) . . . . ?
C4 C5 C10 C9 179.43(9) . . . . ?
C6 C5 C10 C1 -176.27(8) . . . . ?
C4 C5 C10 C1 1.51(13) . . . . ?
N1 C1 C10 C9 -1.17(17) . . . . ?
C2 C1 C10 C9 -177.41(9) . . . . ?
N1 C1 C10 C5 176.58(10) . . . . ?
C2 C1 C10 C5 0.34(13) . . . . ?
C1 N1 C11 C12 -71.41(14) . . . . ?
N2 N1 C11 C12 114.94(10) . . . . ?
N1 C11 C12 C13 -20.67(14) . . . . ?
N1 C11 C12 C17 159.23(10) . . . . ?
C17 C12 C13 C14 -1.38(17) . . . . ?
C11 C12 C13 C14 178.52(11) . . . . ?
C12 C13 C14 C15 -0.20(19) . . . . ?
C13 C14 C15 C16 1.96(19) . . . . ?
C13 C14 C15 C18 -178.13(13) . . . . ?
C14 C15 C16 C17 -2.17(19) . . . . ?
C18 C15 C16 C17 177.93(13) . . . . ?
C15 C16 C17 C12 0.62(19) . . . . ?
C13 C12 C17 C16 1.17(17) . . . . ?
C11 C12 C17 C16 -178.73(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 32.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.406
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.057
#=============================================================================
data_is_ag506ff
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H11 F3 N4 O4'
_chemical_formula_sum
'C17 H11 F3 N4 O4'
_chemical_formula_weight 392.30
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'
'F' 'F' 0.0171 0.0103
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.7337(2)
_cell_length_b 9.7692(2)
_cell_length_c 11.6204(3)
_cell_angle_alpha 99.7090(10)
_cell_angle_beta 95.9810(10)
_cell_angle_gamma 106.2500(10)
_cell_volume 820.10(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 9908
_cell_measurement_theta_min 4.439
_cell_measurement_theta_max 63.888
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.589
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 400
_exptl_absorpt_coefficient_mu 0.138
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9293
_exptl_absorpt_correction_T_max 0.9863
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 27547
_diffrn_reflns_av_R_equivalents 0.0207
_diffrn_reflns_av_sigmaI/netI 0.0254
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.78
_diffrn_reflns_theta_max 32.50
_reflns_number_total 5917
_reflns_number_gt 4327
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material 'SHELXL-97'
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.2994P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5917
_refine_ls_number_parameters 254
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0698
_refine_ls_R_factor_gt 0.0459
_refine_ls_wR_factor_ref 0.1305
_refine_ls_wR_factor_gt 0.1128
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.15188(15) 0.79293(12) 0.64624(9) 0.0277(2) Uani 1 1 d . . .
N2 N 0.14431(15) 0.70254(12) 0.72368(9) 0.0262(2) Uani 1 1 d . . .
N3 N 0.27413(13) 0.49020(11) 0.48839(9) 0.0229(2) Uani 1 1 d . . .
N4 N 0.55541(17) 0.34257(13) 0.90683(10) 0.0319(2) Uani 1 1 d . . .
O1 O 0.26153(13) 0.50018(10) 0.38380(8) 0.0303(2) Uani 1 1 d . . .
O2 O 0.31289(15) 0.38934(11) 0.52433(9) 0.0354(2) Uani 1 1 d . . .
O3 O 0.69295(14) 0.42515(14) 0.88525(10) 0.0445(3) Uani 1 1 d . . .
O4 O 0.55676(19) 0.24576(15) 0.96105(12) 0.0550(3) Uani 1 1 d . . .
F1 F 0.35919(19) 1.21596(10) 0.23968(10) 0.0654(3) Uani 1 1 d . . .
F2 F 0.20623(15) 1.03102(11) 0.10744(9) 0.0552(3) Uani 1 1 d . . .
F3 F 0.49492(15) 1.07641(13) 0.15203(10) 0.0597(3) Uani 1 1 d . . .
C1 C 0.20910(16) 0.73161(13) 0.55222(10) 0.0235(2) Uani 1 1 d . . .
C2 C 0.23749(15) 0.59989(13) 0.57168(10) 0.0215(2) Uani 1 1 d . . .
C3 C 0.19694(15) 0.58539(13) 0.68414(10) 0.0224(2) Uani 1 1 d . . .
C4 C 0.20699(15) 0.47781(13) 0.75763(10) 0.0223(2) Uani 1 1 d . . .
C5 C 0.37432(15) 0.45672(13) 0.79165(10) 0.0220(2) Uani 1 1 d . . .
H5 H 0.4814 0.5060 0.7643 0.026 Uiso 1 1 calc R . .
C6 C 0.37884(17) 0.36136(14) 0.86684(10) 0.0246(2) Uani 1 1 d . . .
C7 C 0.22565(19) 0.28575(15) 0.90818(11) 0.0308(3) Uani 1 1 d . . .
H7 H 0.2335 0.2198 0.9586 0.037 Uiso 1 1 calc R . .
C8 C 0.06149(19) 0.30915(16) 0.87393(12) 0.0335(3) Uani 1 1 d . . .
H8 H -0.0451 0.2600 0.9019 0.040 Uiso 1 1 calc R . .
C9 C 0.05179(17) 0.40404(15) 0.79896(11) 0.0289(3) Uani 1 1 d . . .
H9 H -0.0618 0.4190 0.7755 0.035 Uiso 1 1 calc R . .
C10 C 0.0856(2) 0.74323(18) 0.83629(12) 0.0367(3) Uani 1 1 d . . .
H10A H -0.0464 0.6986 0.8291 0.055 Uiso 1 1 calc R . .
H10B H 0.1151 0.8495 0.8577 0.055 Uiso 1 1 calc R . .
H10C H 0.1487 0.7089 0.8978 0.055 Uiso 1 1 calc R . .
C11 C 0.24339(17) 0.81299(13) 0.45662(10) 0.0246(2) Uani 1 1 d . . .
C12 C 0.39898(18) 0.82468(14) 0.40374(11) 0.0264(2) Uani 1 1 d . . .
H12 H 0.4812 0.7733 0.4246 0.032 Uiso 1 1 calc R . .
C13 C 0.43402(19) 0.91164(14) 0.32038(11) 0.0281(2) Uani 1 1 d . . .
H13 H 0.5401 0.9199 0.2842 0.034 Uiso 1 1 calc R . .
C14 C 0.31294(19) 0.98637(14) 0.29038(11) 0.0294(3) Uani 1 1 d . . .
C15 C 0.1589(2) 0.97701(15) 0.34389(12) 0.0338(3) Uani 1 1 d . . .
H15 H 0.0781 1.0299 0.3240 0.041 Uiso 1 1 calc R . .
C16 C 0.1239(2) 0.88989(15) 0.42657(12) 0.0309(3) Uani 1 1 d . . .
H16 H 0.0182 0.8825 0.4630 0.037 Uiso 1 1 calc R . .
C17 C 0.3449(2) 1.07686(16) 0.19820(13) 0.0366(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
N1 0.0383(6) 0.0336(6) 0.0209(5) 0.0115(4) 0.0068(4) 0.0219(5)
N2 0.0323(5) 0.0352(6) 0.0196(5) 0.0109(4) 0.0073(4) 0.0197(4)
N3 0.0250(4) 0.0265(5) 0.0222(5) 0.0096(4) 0.0056(4) 0.0121(4)
N4 0.0411(6) 0.0394(6) 0.0228(5) 0.0077(4) 0.0017(4) 0.0249(5)
O1 0.0430(5) 0.0339(5) 0.0196(4) 0.0086(4) 0.0066(4) 0.0182(4)
O2 0.0547(6) 0.0342(5) 0.0316(5) 0.0157(4) 0.0118(4) 0.0294(5)
O3 0.0333(5) 0.0646(8) 0.0458(6) 0.0179(6) 0.0072(5) 0.0271(5)
O4 0.0675(8) 0.0599(8) 0.0541(7) 0.0316(6) -0.0005(6) 0.0375(7)
F1 0.1164(10) 0.0256(5) 0.0538(6) 0.0183(4) 0.0086(6) 0.0168(5)
F2 0.0683(7) 0.0525(6) 0.0368(5) 0.0274(5) -0.0110(5) 0.0022(5)
F3 0.0655(7) 0.0735(7) 0.0562(7) 0.0465(6) 0.0218(5) 0.0229(6)
C1 0.0288(5) 0.0279(6) 0.0199(5) 0.0098(4) 0.0043(4) 0.0155(5)
C2 0.0241(5) 0.0262(6) 0.0197(5) 0.0093(4) 0.0051(4) 0.0131(4)
C3 0.0219(5) 0.0299(6) 0.0203(5) 0.0102(4) 0.0039(4) 0.0126(4)
C4 0.0241(5) 0.0288(6) 0.0185(5) 0.0110(4) 0.0048(4) 0.0109(4)
C5 0.0242(5) 0.0260(6) 0.0199(5) 0.0094(4) 0.0051(4) 0.0107(4)
C6 0.0311(6) 0.0278(6) 0.0190(5) 0.0074(4) 0.0019(4) 0.0149(5)
C7 0.0425(7) 0.0295(6) 0.0226(6) 0.0134(5) 0.0058(5) 0.0092(5)
C8 0.0320(6) 0.0407(8) 0.0267(6) 0.0162(6) 0.0074(5) 0.0031(5)
C9 0.0237(5) 0.0413(7) 0.0236(6) 0.0136(5) 0.0050(4) 0.0087(5)
C10 0.0494(8) 0.0530(9) 0.0221(6) 0.0124(6) 0.0142(6) 0.0327(7)
C11 0.0350(6) 0.0249(6) 0.0190(5) 0.0078(4) 0.0036(4) 0.0155(5)
C12 0.0339(6) 0.0263(6) 0.0239(6) 0.0095(5) 0.0042(5) 0.0146(5)
C13 0.0376(6) 0.0252(6) 0.0236(6) 0.0090(5) 0.0063(5) 0.0102(5)
C14 0.0458(7) 0.0232(6) 0.0209(5) 0.0085(5) 0.0015(5) 0.0123(5)
C15 0.0507(8) 0.0334(7) 0.0281(6) 0.0137(5) 0.0055(6) 0.0258(6)
C16 0.0430(7) 0.0355(7) 0.0254(6) 0.0126(5) 0.0088(5) 0.0246(6)
C17 0.0521(8) 0.0282(7) 0.0297(7) 0.0140(5) 0.0013(6) 0.0096(6)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.3330(15) . ?
N1 N2 1.3575(14) . ?
N2 C3 1.3450(15) . ?
N2 C10 1.4580(16) . ?
N3 O2 1.2302(13) . ?
N3 O1 1.2315(13) . ?
N3 C2 1.4293(15) . ?
N4 O3 1.2201(17) . ?
N4 O4 1.2235(16) . ?
N4 C6 1.4667(16) . ?
F1 C17 1.3324(18) . ?
F2 C17 1.3413(18) . ?
F3 C17 1.3287(19) . ?
C1 C2 1.4145(16) . ?
C1 C11 1.4757(16) . ?
C2 C3 1.3961(15) . ?
C3 C4 1.4747(16) . ?
C4 C9 1.3941(16) . ?
C4 C5 1.3941(16) . ?
C5 C6 1.3852(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3887(18) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3862(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3926(17) . ?
C11 C16 1.3962(17) . ?
C12 C13 1.3917(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3899(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 C17 1.4974(18) . ?
C15 C16 1.3862(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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
C1 N1 N2 106.06(10) . . ?
C3 N2 N1 113.20(9) . . ?
C3 N2 C10 128.68(11) . . ?
N1 N2 C10 118.11(10) . . ?
O2 N3 O1 123.43(10) . . ?
O2 N3 C2 118.43(10) . . ?
O1 N3 C2 118.12(9) . . ?
O3 N4 O4 123.60(12) . . ?
O3 N4 C6 118.27(11) . . ?
O4 N4 C6 118.13(12) . . ?
N1 C1 C2 109.11(10) . . ?
N1 C1 C11 117.77(10) . . ?
C2 C1 C11 132.93(10) . . ?
C3 C2 C1 106.82(10) . . ?
C3 C2 N3 124.91(10) . . ?
C1 C2 N3 127.70(10) . . ?
N2 C3 C2 104.79(10) . . ?
N2 C3 C4 121.54(10) . . ?
C2 C3 C4 133.64(11) . . ?
C9 C4 C5 120.07(11) . . ?
C9 C4 C3 120.03(10) . . ?
C5 C4 C3 119.78(10) . . ?
C6 C5 C4 117.61(10) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C7 123.27(11) . . ?
C5 C6 N4 118.09(11) . . ?
C7 C6 N4 118.63(11) . . ?
C8 C7 C6 118.09(12) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 120.26(12) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.69(11) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 119.77(11) . . ?
C12 C11 C1 121.58(10) . . ?
C16 C11 C1 118.41(11) . . ?
C13 C12 C11 120.00(11) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.62(12) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.76(11) . . ?
C15 C14 C17 118.72(12) . . ?
C13 C14 C17 120.51(13) . . ?
C16 C15 C14 119.51(12) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 120.32(12) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
F3 C17 F1 106.62(13) . . ?
F3 C17 F2 106.50(13) . . ?
F1 C17 F2 105.23(13) . . ?
F3 C17 C14 113.51(12) . . ?
F1 C17 C14 112.52(12) . . ?
F2 C17 C14 111.89(12) . . ?
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
C1 N1 N2 C3 0.84(14) . . . . ?
C1 N1 N2 C10 179.82(12) . . . . ?
N2 N1 C1 C2 0.08(14) . . . . ?
N2 N1 C1 C11 -175.48(11) . . . . ?
N1 C1 C2 C3 -0.92(14) . . . . ?
C11 C1 C2 C3 173.73(13) . . . . ?
N1 C1 C2 N3 170.63(11) . . . . ?
C11 C1 C2 N3 -14.7(2) . . . . ?
O2 N3 C2 C3 -16.94(17) . . . . ?
O1 N3 C2 C3 161.60(11) . . . . ?
O2 N3 C2 C1 172.94(12) . . . . ?
O1 N3 C2 C1 -8.51(18) . . . . ?
N1 N2 C3 C2 -1.39(14) . . . . ?
C10 N2 C3 C2 179.76(13) . . . . ?
N1 N2 C3 C4 176.98(10) . . . . ?
C10 N2 C3 C4 -1.9(2) . . . . ?
C1 C2 C3 N2 1.35(13) . . . . ?
N3 C2 C3 N2 -170.49(11) . . . . ?
C1 C2 C3 C4 -176.73(13) . . . . ?
N3 C2 C3 C4 11.4(2) . . . . ?
N2 C3 C4 C9 58.71(17) . . . . ?
C2 C3 C4 C9 -123.47(15) . . . . ?
N2 C3 C4 C5 -117.35(13) . . . . ?
C2 C3 C4 C5 60.48(19) . . . . ?
C9 C4 C5 C6 -0.09(18) . . . . ?
C3 C4 C5 C6 175.97(11) . . . . ?
C4 C5 C6 C7 0.71(19) . . . . ?
C4 C5 C6 N4 -177.71(11) . . . . ?
O3 N4 C6 C5 9.55(18) . . . . ?
O4 N4 C6 C5 -171.15(12) . . . . ?
O3 N4 C6 C7 -168.94(12) . . . . ?
O4 N4 C6 C7 10.35(18) . . . . ?
C5 C6 C7 C8 -1.1(2) . . . . ?
N4 C6 C7 C8 177.26(12) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C4 -0.4(2) . . . . ?
C5 C4 C9 C8 -0.1(2) . . . . ?
C3 C4 C9 C8 -176.10(12) . . . . ?
N1 C1 C11 C12 135.29(13) . . . . ?
C2 C1 C11 C12 -39.0(2) . . . . ?
N1 C1 C11 C16 -39.12(18) . . . . ?
C2 C1 C11 C16 146.60(14) . . . . ?
C16 C11 C12 C13 -0.64(19) . . . . ?
C1 C11 C12 C13 -174.98(12) . . . . ?
C11 C12 C13 C14 -0.03(19) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C12 C13 C14 C17 -178.10(12) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C17 C14 C15 C16 177.87(13) . . . . ?
C14 C15 C16 C11 0.5(2) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C1 C11 C16 C15 174.91(13) . . . . ?
C15 C14 C17 F3 -179.19(13) . . . . ?
C13 C14 C17 F3 -0.10(19) . . . . ?
C15 C14 C17 F1 59.61(19) . . . . ?
C13 C14 C17 F1 -121.30(15) . . . . ?
C15 C14 C17 F2 -58.62(18) . . . . ?
C13 C14 C17 F2 120.47(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 32.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.394
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.051
#=============================================================================
data_is_ag636lf
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H15 N3 O2'
_chemical_formula_sum
'C17 H15 N3 O2'
_chemical_formula_weight 293.32
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'C c'
_symmetry_space_group_name_Hall 'C -2yc'
_symmetry_Int_Tables_number 9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a 12.4481(14)
_cell_length_b 14.0884(16)
_cell_length_c 9.7990(11)
_cell_angle_alpha 90.00
_cell_angle_beta 121.412(3)
_cell_angle_gamma 90.00
_cell_volume 1466.6(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 2095
_cell_measurement_theta_min 4.802
_cell_measurement_theta_max 49.561
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.328
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9650
_exptl_absorpt_correction_T_max 0.9929
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8140
_diffrn_reflns_av_R_equivalents 0.0327
_diffrn_reflns_av_sigmaI/netI 0.0578
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.61
_diffrn_reflns_theta_max 29.00
_reflns_number_total 3675
_reflns_number_gt 2653
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex V7.51A'
_computing_cell_refinement 'Bruker Apex V7.51A'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material 'SHELXL-97'
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.6(16)
_refine_ls_number_reflns 3675
_refine_ls_number_parameters 205
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0801
_refine_ls_R_factor_gt 0.0523
_refine_ls_wR_factor_ref 0.1312
_refine_ls_wR_factor_gt 0.1155
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.5377(2) 0.93647(14) 0.6077(3) 0.0388(5) Uani 1 1 d . . .
N2 N 0.3421(3) 0.79433(19) 0.2952(3) 0.0556(7) Uani 1 1 d . . .
N3 N 0.56942(19) 0.81169(15) 0.8640(2) 0.0325(5) Uani 1 1 d . . .
O1 O 0.5974(2) 0.97153(14) 0.7436(2) 0.0499(5) Uani 1 1 d . . .
O2 O 0.5160(2) 0.98159(14) 0.4857(2) 0.0511(5) Uani 1 1 d . . .
C1 C 0.4903(2) 0.84301(17) 0.5864(3) 0.0326(5) Uani 1 1 d . . .
C2 C 0.4110(3) 0.81506(19) 0.4254(3) 0.0375(6) Uani 1 1 d . . .
C3 C 0.5133(2) 0.78348(18) 0.7139(3) 0.0290(5) Uani 1 1 d . . .
C4 C 0.4654(2) 0.68460(17) 0.6740(3) 0.0279(5) Uani 1 1 d . . .
C5 C 0.5031(2) 0.62465(18) 0.5942(3) 0.0345(5) Uani 1 1 d . . .
H5 H 0.5597 0.6466 0.5636 0.041 Uiso 1 1 calc R . .
C6 C 0.4576(2) 0.53295(19) 0.5596(3) 0.0393(6) Uani 1 1 d . . .
H6 H 0.4851 0.4916 0.5071 0.047 Uiso 1 1 calc R . .
C7 C 0.3719(3) 0.49958(18) 0.6003(3) 0.0393(6) Uani 1 1 d . . .
C8 C 0.3335(2) 0.56117(17) 0.6777(3) 0.0347(6) Uani 1 1 d . . .
H8 H 0.2738 0.5405 0.7039 0.042 Uiso 1 1 calc R . .
C9 C 0.3816(2) 0.65219(16) 0.7169(3) 0.0289(5) Uani 1 1 d . . .
H9 H 0.3572 0.6928 0.7734 0.035 Uiso 1 1 calc R . .
C10 C 0.3178(4) 0.4029(2) 0.5602(5) 0.0688(10) Uani 1 1 d . . .
H10A H 0.3219 0.3745 0.6541 0.103 Uiso 1 1 calc R . .
H10B H 0.3658 0.3638 0.5278 0.103 Uiso 1 1 calc R . .
H10C H 0.2298 0.4063 0.4723 0.103 Uiso 1 1 calc R . .
C11 C 0.6086(2) 0.75297(17) 1.0013(2) 0.0283(5) Uani 1 1 d . . .
C12 C 0.6779(2) 0.67119(16) 1.0246(3) 0.0299(5) Uani 1 1 d . . .
H12 H 0.6968 0.6516 0.9466 0.036 Uiso 1 1 calc R . .
C13 C 0.7194(2) 0.61832(16) 1.1621(3) 0.0301(5) Uani 1 1 d . . .
H13 H 0.7676 0.5626 1.1780 0.036 Uiso 1 1 calc R . .
C14 C 0.6923(2) 0.64467(17) 1.2777(3) 0.0318(5) Uani 1 1 d . . .
C15 C 0.6226(2) 0.72696(18) 1.2509(3) 0.0356(6) Uani 1 1 d . . .
H15 H 0.6031 0.7466 1.3283 0.043 Uiso 1 1 calc R . .
C16 C 0.5807(2) 0.78117(16) 1.1144(3) 0.0345(5) Uani 1 1 d . . .
H16 H 0.5331 0.8372 1.0986 0.041 Uiso 1 1 calc R . .
C17 C 0.7323(3) 0.5843(2) 1.4228(3) 0.0429(7) Uani 1 1 d . . .
H17A H 0.7653 0.6250 1.5174 0.064 Uiso 1 1 calc R . .
H17B H 0.7980 0.5400 1.4367 0.064 Uiso 1 1 calc R . .
H17C H 0.6598 0.5485 1.4089 0.064 Uiso 1 1 calc R . .
H1 H 0.591(3) 0.874(2) 0.881(3) 0.050(8) Uiso 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 0.0419(13) 0.0332(11) 0.0471(14) 0.0088(10) 0.0273(11) -0.0002(10)
N2 0.0653(17) 0.0597(16) 0.0349(14) 0.0047(11) 0.0212(13) 0.0038(14)
N3 0.0366(11) 0.0265(10) 0.0314(11) -0.0005(8) 0.0156(10) -0.0040(9)
O1 0.0644(13) 0.0380(10) 0.0472(12) -0.0017(9) 0.0290(11) -0.0114(10)
O2 0.0647(13) 0.0420(10) 0.0537(12) 0.0181(9) 0.0358(11) 0.0006(10)
C1 0.0332(13) 0.0312(13) 0.0348(14) 0.0061(10) 0.0188(11) 0.0033(10)
C2 0.0408(15) 0.0385(14) 0.0360(15) 0.0086(11) 0.0220(13) 0.0059(11)
C3 0.0261(11) 0.0300(12) 0.0320(13) 0.0027(9) 0.0160(10) -0.0003(9)
C4 0.0256(11) 0.0317(12) 0.0225(11) 0.0025(9) 0.0097(9) 0.0016(10)
C5 0.0335(12) 0.0395(13) 0.0286(13) -0.0001(10) 0.0149(11) 0.0019(11)
C6 0.0381(14) 0.0396(14) 0.0325(14) -0.0019(11) 0.0131(12) 0.0093(12)
C7 0.0389(14) 0.0276(13) 0.0325(13) 0.0012(10) 0.0054(12) 0.0016(11)
C8 0.0332(13) 0.0322(12) 0.0320(13) 0.0040(10) 0.0123(11) -0.0014(11)
C9 0.0286(11) 0.0296(11) 0.0254(11) 0.0022(9) 0.0120(10) 0.0008(10)
C10 0.081(2) 0.0431(17) 0.075(2) 0.0020(16) 0.035(2) 0.0041(18)
C11 0.0279(11) 0.0284(11) 0.0262(12) 0.0008(9) 0.0124(10) -0.0060(10)
C12 0.0315(12) 0.0324(12) 0.0266(12) -0.0053(9) 0.0157(10) -0.0032(10)
C13 0.0320(12) 0.0264(12) 0.0296(12) -0.0018(9) 0.0144(11) -0.0007(10)
C14 0.0335(12) 0.0312(13) 0.0287(13) -0.0034(10) 0.0149(11) -0.0048(11)
C15 0.0402(14) 0.0394(14) 0.0332(13) -0.0051(10) 0.0233(12) -0.0018(11)
C16 0.0380(13) 0.0277(12) 0.0387(14) -0.0028(10) 0.0205(12) 0.0024(11)
C17 0.0571(17) 0.0409(15) 0.0309(14) 0.0040(11) 0.0230(13) 0.0004(13)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 O1 1.241(3) . ?
N1 O2 1.253(3) . ?
N1 C1 1.414(3) . ?
N2 C2 1.144(3) . ?
N3 C3 1.318(3) . ?
N3 C11 1.431(3) . ?
N3 H1 0.91(3) . ?
C1 C3 1.405(3) . ?
C1 C2 1.413(4) . ?
C3 C4 1.485(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.389(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 C10 1.479(4) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.382(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(3) . ?
C14 C17 1.501(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 N1 O2 122.2(2) . . ?
O1 N1 C1 119.9(2) . . ?
O2 N1 C1 117.8(2) . . ?
C3 N3 C11 126.7(2) . . ?
C3 N3 H1 115.7(18) . . ?
C11 N3 H1 117.4(19) . . ?
C3 C1 C2 121.8(2) . . ?
C3 C1 N1 123.3(2) . . ?
C2 C1 N1 114.8(2) . . ?
N2 C2 C1 176.8(3) . . ?
N3 C3 C1 123.8(2) . . ?
N3 C3 C4 118.9(2) . . ?
C1 C3 C4 117.3(2) . . ?
C5 C4 C9 119.8(2) . . ?
C5 C4 C3 120.8(2) . . ?
C9 C4 C3 119.3(2) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 C10 118.8(3) . . ?
C6 C7 C10 122.9(3) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 120.2(2) . . ?
C16 C11 N3 118.9(2) . . ?
C12 C11 N3 120.9(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C17 121.2(2) . . ?
C13 C14 C17 121.2(2) . . ?
C16 C15 C14 121.8(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C11 C16 C15 119.4(2) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
O1 N1 C1 C3 -4.0(4) . . . . ?
O2 N1 C1 C3 176.8(2) . . . . ?
O1 N1 C1 C2 172.5(2) . . . . ?
O2 N1 C1 C2 -6.7(3) . . . . ?
C3 C1 C2 N2 91(5) . . . . ?
N1 C1 C2 N2 -86(5) . . . . ?
C11 N3 C3 C1 -172.3(2) . . . . ?
C11 N3 C3 C4 10.8(3) . . . . ?
C2 C1 C3 N3 -168.7(2) . . . . ?
N1 C1 C3 N3 7.6(4) . . . . ?
C2 C1 C3 C4 8.3(3) . . . . ?
N1 C1 C3 C4 -175.4(2) . . . . ?
N3 C3 C4 C5 -124.5(2) . . . . ?
C1 C3 C4 C5 58.4(3) . . . . ?
N3 C3 C4 C9 55.7(3) . . . . ?
C1 C3 C4 C9 -121.4(2) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C10 177.8(3) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C10 C7 C8 C9 -179.8(3) . . . . ?
C7 C8 C9 C4 2.4(3) . . . . ?
C5 C4 C9 C8 -1.3(3) . . . . ?
C3 C4 C9 C8 178.5(2) . . . . ?
C3 N3 C11 C16 -133.6(3) . . . . ?
C3 N3 C11 C12 49.0(3) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
N3 C11 C12 C13 177.0(2) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C12 C13 C14 C17 177.0(2) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C17 C14 C15 C16 -177.3(3) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
N3 C11 C16 C15 -177.4(2) . . . . ?
C14 C15 C16 C11 0.0(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.223
_refine_diff_density_min -0.293
_refine_diff_density_rms 0.045