#------------------------------------------------------------------------------
#$Date: 2022-10-27 04:05:47 +0300 (Thu, 27 Oct 2022) $
#$Revision: 278830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158953.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158953
loop_
_publ_author_name
'Itakhunov, Radik N.'
'Odin, Ivan S.'
'Gusev, Dmitry M.'
'Grabovskiy, Stanislav A.'
'Gordon, Kareem V.'
'Vologzhanina, Anna V.'
'Sokov, Sergey A.'
'Sosnin, Ilya M.'
'Golovanov, Alexander A.'
_publ_section_title
;
 Cyclization of arylhydrazones of cross-conjugated enynones: synthesis of
 luminescent styryl-1H-pyrazoles and propenyl-1H-pyrazoles
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01427K
_journal_year                    2022
_chemical_formula_moiety         'C23 H18 N2'
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.624(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   42.8149(15)
_cell_length_b                   5.8284(2)
_cell_length_c                   30.8813(9)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.17
_cell_volume                     6764.4(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Quest Photon area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1423
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            48463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.688
_diffrn_reflns_theta_min         1.958
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1586 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.7578.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       needle
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         10386
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1777
_refine_ls_R_factor_gt           0.0882
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0254P)²+22.2409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5364
_reflns_number_total             10386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01427k2.cif
_cod_data_source_block           gol222
_cod_database_code               7158953
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Rigid body (RIGU) restrains
 C5A, C6A, C7A, C8A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C2A(H2A), C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.75274(6) 0.7185(4) 0.62427(8) 0.0238(5) Uani 1 1 d . . . . .
N2 N 0.72666(6) 0.8799(4) 0.61200(9) 0.0293(6) Uani 1 1 d . . . . .
C1 C 0.75627(7) 0.5780(5) 0.66182(10) 0.0222(6) Uani 1 1 d . . . . .
C2 C 0.73078(8) 0.6520(5) 0.67405(11) 0.0294(7) Uani 1 1 d . . . . .
H2 H 0.725890 0.589688 0.698595 0.035 Uiso 1 1 calc R U . . .
C3 C 0.71362(7) 0.8383(5) 0.64273(11) 0.0305(7) Uani 1 1 d . . . . .
C4 C 0.68505(8) 0.9968(6) 0.63880(11) 0.0339(7) Uani 1 1 d . . . . .
H4 H 0.678904 1.119488 0.615907 0.041 Uiso 1 1 calc R U . . .
C5 C 0.66789(8) 0.9836(6) 0.66336(12) 0.0353(7) Uani 1 1 d . . . . .
H5 H 0.674130 0.864508 0.687082 0.042 Uiso 1 1 calc R U . . .
C6 C 0.63903(7) 1.1427(5) 0.65693(11) 0.0276(6) Uani 1 1 d . . . . .
C7 C 0.61599(8) 1.0715(5) 0.67412(10) 0.0303(7) Uani 1 1 d . . . . .
H7 H 0.619938 0.928576 0.690718 0.036 Uiso 1 1 calc R U . . .
C8 C 0.58745(8) 1.2054(6) 0.66744(11) 0.0331(7) Uani 1 1 d . . . . .
H8 H 0.571813 1.153348 0.679134 0.040 Uiso 1 1 calc R U . . .
C9 C 0.58156(8) 1.4134(5) 0.64399(11) 0.0303(7) Uani 1 1 d . . . . .
H9 H 0.561807 1.504940 0.639237 0.036 Uiso 1 1 calc R U . . .
C10 C 0.60447(8) 1.4888(5) 0.62735(11) 0.0286(6) Uani 1 1 d . . . . .
H10 H 0.600611 1.633684 0.611483 0.034 Uiso 1 1 calc R U . . .
C11 C 0.63316(8) 1.3546(5) 0.63362(11) 0.0285(6) Uani 1 1 d . . . . .
H11 H 0.648774 1.407638 0.621976 0.034 Uiso 1 1 calc R U . . .
C12 C 0.78411(7) 0.4015(5) 0.68503(10) 0.0222(6) Uani 1 1 d . . . . .
C13 C 0.77727(8) 0.2090(5) 0.70567(10) 0.0261(6) Uani 1 1 d . . . . .
H13 H 0.754643 0.191183 0.703933 0.031 Uiso 1 1 calc R U . . .
C14 C 0.80318(8) 0.0428(5) 0.72876(10) 0.0303(7) Uani 1 1 d . . . . .
H14 H 0.798200 -0.087703 0.742858 0.036 Uiso 1 1 calc R U . . .
C15 C 0.83633(8) 0.0652(5) 0.73147(10) 0.0297(7) Uani 1 1 d . . . . .
H15 H 0.853867 -0.050584 0.746811 0.036 Uiso 1 1 calc R U . . .
C16 C 0.84360(8) 0.2580(5) 0.71160(10) 0.0274(6) Uani 1 1 d . . . . .
H16 H 0.866326 0.275406 0.713612 0.033 Uiso 1 1 calc R U . . .
C17 C 0.81783(7) 0.4258(5) 0.68876(10) 0.0237(6) Uani 1 1 d . . . . .
H17 H 0.823128 0.558219 0.675553 0.028 Uiso 1 1 calc R U . . .
C18 C 0.76989(7) 0.7088(5) 0.59442(10) 0.0228(6) Uani 1 1 d . . . . .
C19 C 0.78853(7) 0.8986(5) 0.59226(10) 0.0273(6) Uani 1 1 d . . . . .
H19 H 0.790571 1.031239 0.611336 0.033 Uiso 1 1 calc R U . . .
C20 C 0.80417(8) 0.8936(6) 0.56207(11) 0.0335(7) Uani 1 1 d . . . . .
H20 H 0.817040 1.022972 0.560371 0.040 Uiso 1 1 calc R U . . .
C21 C 0.80104(8) 0.7004(5) 0.53445(11) 0.0323(7) Uani 1 1 d . . . . .
H21 H 0.811548 0.697882 0.513458 0.039 Uiso 1 1 calc R U . . .
C22 C 0.78275(8) 0.5108(5) 0.53713(11) 0.0291(7) Uani 1 1 d . . . . .
H22 H 0.780953 0.377943 0.518259 0.035 Uiso 1 1 calc R U . . .
C23 C 0.76698(7) 0.5134(5) 0.56726(10) 0.0251(6) Uani 1 1 d . . . . .
H23 H 0.754386 0.383091 0.569226 0.030 Uiso 1 1 calc R U . . .
N1A N 0.53482(6) 0.2779(4) 0.41447(8) 0.0223(5) Uani 1 1 d . . . . .
N2A N 0.50335(6) 0.3077(4) 0.37214(8) 0.0264(5) Uani 1 1 d . . . . .
C1A C 0.56011(7) 0.4275(5) 0.41695(10) 0.0202(5) Uani 1 1 d . . . . .
C2A C 0.54455(7) 0.5630(5) 0.37556(10) 0.0238(6) Uani 1 1 d . . . . .
H2A H 0.555290 0.684946 0.367010 0.029 Uiso 1 1 calc R U . . .
C3A C 0.50961(8) 0.4836(5) 0.34866(10) 0.0270(6) Uani 1 1 d . . . . .
C4A C 0.47850(9) 0.5567(6) 0.30245(12) 0.0384(8) Uani 1 1 d . . . . .
H4A H 0.459155 0.452289 0.287700 0.046 Uiso 1 1 calc R U . . .
C5A C 0.47517(9) 0.7499(6) 0.28018(12) 0.0371(8) Uani 1 1 d . . . . .
H5A H 0.494682 0.853280 0.294636 0.044 Uiso 1 1 calc R U . . .
C6A C 0.44385(7) 0.8246(5) 0.23439(10) 0.0250(6) Uani 1 1 d . . . . .
C7A C 0.44525(8) 1.0395(6) 0.21382(13) 0.0377(8) Uani 1 1 d . . . . .
H7A H 0.465588 1.135202 0.230051 0.045 Uiso 1 1 calc R U . . .
C8A C 0.41562(10) 1.1099(6) 0.16829(13) 0.0406(8) Uani 1 1 d . . . . .
H8A H 0.416088 1.252781 0.153802 0.049 Uiso 1 1 calc R U . . .
C9A C 0.38674(9) 0.9699(7) 0.14596(13) 0.0436(9) Uani 1 1 d . . . . .
H9A H 0.367145 1.015317 0.115510 0.052 Uiso 1 1 calc R U . . .
C10A C 0.38550(9) 0.7690(7) 0.16623(13) 0.0463(9) Uani 1 1 d . . . . .
H10A H 0.364883 0.675545 0.150226 0.056 Uiso 1 1 calc R U . . .
C11A C 0.41303(8) 0.6979(6) 0.20889(12) 0.0353(7) Uani 1 1 d . . . . .
H11A H 0.411215 0.554323 0.222081 0.042 Uiso 1 1 calc R U . . .
C12A C 0.59676(7) 0.4399(5) 0.45769(10) 0.0213(6) Uani 1 1 d . . . . .
C13A C 0.60815(7) 0.6384(5) 0.48609(10) 0.0229(6) Uani 1 1 d . . . . .
H13A H 0.592550 0.765884 0.478287 0.027 Uiso 1 1 calc R U . . .
C14A C 0.64215(7) 0.6504(5) 0.52564(11) 0.0271(6) Uani 1 1 d . . . . .
H14A H 0.649729 0.785794 0.545105 0.032 Uiso 1 1 calc R U . . .
C15A C 0.66523(7) 0.4660(5) 0.53705(10) 0.0250(6) Uani 1 1 d . . . . .
H15A H 0.688529 0.474582 0.564343 0.030 Uiso 1 1 calc R U . . .
C16A C 0.65414(7) 0.2691(5) 0.50846(10) 0.0246(6) Uani 1 1 d . . . . .
H16A H 0.669989 0.143180 0.515954 0.029 Uiso 1 1 calc R U . . .
C17A C 0.62004(7) 0.2553(5) 0.46901(10) 0.0235(6) Uani 1 1 d . . . . .
H17A H 0.612523 0.119587 0.449634 0.028 Uiso 1 1 calc R U . . .
C18A C 0.53639(7) 0.1132(5) 0.45004(10) 0.0203(5) Uani 1 1 d . . . . .
C19A C 0.55669(7) 0.1556(5) 0.50038(10) 0.0215(6) Uani 1 1 d . . . . .
H19A H 0.570179 0.292783 0.511804 0.026 Uiso 1 1 calc R U . . .
C20A C 0.55693(7) -0.0053(5) 0.53357(10) 0.0244(6) Uani 1 1 d . . . . .
H20A H 0.570934 0.021271 0.567987 0.029 Uiso 1 1 calc R U . . .
C21A C 0.53699(7) -0.2043(5) 0.51713(11) 0.0269(6) Uani 1 1 d . . . . .
H21A H 0.537469 -0.314190 0.540155 0.032 Uiso 1 1 calc R U . . .
C22A C 0.51631(7) -0.2425(5) 0.46686(11) 0.0270(6) Uani 1 1 d . . . . .
H22A H 0.502286 -0.377671 0.455440 0.032 Uiso 1 1 calc R U . . .
C23A C 0.51610(7) -0.0839(5) 0.43337(10) 0.0242(6) Uani 1 1 d . . . . .
H23A H 0.502020 -0.110449 0.398968 0.029 Uiso 1 1 calc R U . . .
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'
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
N2 N1 C1 113.0(2) . . ?
N2 N1 C18 116.9(2) . . ?
C1 N1 C18 129.9(2) . . ?
C3 N2 N1 104.0(2) . . ?
N1 C1 C2 105.3(2) . . ?
N1 C1 C12 124.4(2) . . ?
C2 C1 C12 130.1(3) . . ?
C1 C2 H2 127.0 . . ?
C1 C2 C3 105.9(3) . . ?
C3 C2 H2 127.0 . . ?
N2 C3 C2 111.8(3) . . ?
N2 C3 C4 115.9(3) . . ?
C2 C3 C4 132.3(3) . . ?
C3 C4 H4 116.8 . . ?
C5 C4 C3 126.4(3) . . ?
C5 C4 H4 116.8 . . ?
C4 C5 H5 118.0 . . ?
C4 C5 C6 124.0(3) . . ?
C6 C5 H5 118.0 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 C11 118.5(3) . . ?
C11 C6 C5 123.9(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C1 119.2(3) . . ?
C13 C12 C17 118.7(3) . . ?
C17 C12 C1 122.1(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C19 C18 N1 119.1(3) . . ?
C23 C18 N1 119.9(3) . . ?
C23 C18 C19 121.0(3) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 118.9(3) . . ?
C18 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
N2A N1A C18A 118.7(2) . . ?
C1A N1A N2A 111.4(2) . . ?
C1A N1A C18A 129.8(2) . . ?
C3A N2A N1A 104.5(2) . . ?
N1A C1A C2A 107.3(2) . . ?
N1A C1A C12A 125.0(2) . . ?
C2A C1A C12A 127.7(3) . . ?
C1A C2A H2A 127.3 . . ?
C1A C2A C3A 105.5(2) . . ?
C3A C2A H2A 127.3 . . ?
N2A C3A C2A 111.3(2) . . ?
N2A C3A C4A 114.8(3) . . ?
C2A C3A C4A 133.9(3) . . ?
C3A C4A H4A 117.1 . . ?
C5A C4A C3A 125.9(3) . . ?
C5A C4A H4A 117.1 . . ?
C4A C5A H5A 117.1 . . ?
C4A C5A C6A 125.9(3) . . ?
C6A C5A H5A 117.1 . . ?
C7A C6A C5A 118.4(3) . . ?
C11A C6A C5A 124.8(3) . . ?
C11A C6A C7A 116.8(3) . . ?
C6A C7A H7A 120.5 . . ?
C6A C7A C8A 119.1(3) . . ?
C8A C7A H7A 120.5 . . ?
C7A C8A H8A 120.4 . . ?
C9A C8A C7A 119.2(3) . . ?
C9A C8A H8A 120.4 . . ?
C8A C9A H9A 119.4 . . ?
C10A C9A C8A 121.1(3) . . ?
C10A C9A H9A 119.4 . . ?
C9A C10A H10A 119.5 . . ?
C9A C10A C11A 121.0(4) . . ?
C11A C10A H10A 119.5 . . ?
C6A C11A H11A 118.6 . . ?
C10A C11A C6A 122.9(3) . . ?
C10A C11A H11A 118.6 . . ?
C13A C12A C1A 119.3(2) . . ?
C13A C12A C17A 119.4(3) . . ?
C17A C12A C1A 121.3(3) . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A C12A 120.1(3) . . ?
C14A C13A H13A 119.9 . . ?
C13A C14A H14A 119.8 . . ?
C13A C14A C15A 120.4(3) . . ?
C15A C14A H14A 119.8 . . ?
C14A C15A H15A 120.2 . . ?
C16A C15A C14A 119.7(3) . . ?
C16A C15A H15A 120.2 . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A C15A 120.3(3) . . ?
C17A C16A H16A 119.9 . . ?
C12A C17A H17A 119.9 . . ?
C16A C17A C12A 120.1(3) . . ?
C16A C17A H17A 119.9 . . ?
C19A C18A N1A 120.7(2) . . ?
C23A C18A N1A 118.7(2) . . ?
C23A C18A C19A 120.5(3) . . ?
C18A C19A H19A 120.5 . . ?
C20A C19A C18A 119.0(3) . . ?
C20A C19A H19A 120.5 . . ?
C19A C20A H20A 119.6 . . ?
C21A C20A C19A 120.7(3) . . ?
C21A C20A H20A 119.6 . . ?
C20A C21A H21A 120.1 . . ?
C20A C21A C22A 119.7(3) . . ?
C22A C21A H21A 120.1 . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A C21A 120.0(3) . . ?
C23A C22A H22A 120.0 . . ?
C18A C23A C22A 119.9(3) . . ?
C18A C23A H23A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
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 N2 1.367(3) . ?
N1 C1 1.368(4) . ?
N1 C18 1.429(3) . ?
N2 C3 1.333(4) . ?
C1 C2 1.384(4) . ?
C1 C12 1.474(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.405(4) . ?
C3 C4 1.491(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.286(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.480(4) . ?
C6 C7 1.389(4) . ?
C6 C11 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.372(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 C17 1.399(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(4) . ?
C18 C23 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(4) . ?
C23 H23 0.9500 . ?
N1A N2A 1.366(3) . ?
N1A C1A 1.364(3) . ?
N1A C18A 1.436(3) . ?
N2A C3A 1.354(4) . ?
C1A C2A 1.373(4) . ?
C1A C12A 1.469(4) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.397(4) . ?
C3A C4A 1.473(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.291(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.473(4) . ?
C6A C7A 1.418(4) . ?
C6A C11A 1.382(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.430(5) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.361(5) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.341(5) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.345(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.391(4) . ?
C12A C17A 1.393(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.383(4) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.386(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.386(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.385(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.392(4) . ?
C18A C23A 1.382(4) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.385(4) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.384(4) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.388(4) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.384(4) . ?
C23A H23A 0.9500 . ?
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 N2 C3 C2 -0.5(3) . . . . ?
N1 N2 C3 C4 177.9(2) . . . . ?
N1 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C12 C13 -151.9(3) . . . . ?
N1 C1 C12 C17 30.8(4) . . . . ?
N1 C18 C19 C20 -177.7(3) . . . . ?
N1 C18 C23 C22 177.7(2) . . . . ?
N2 N1 C1 C2 0.6(3) . . . . ?
N2 N1 C1 C12 -174.9(2) . . . . ?
N2 N1 C18 C19 61.7(3) . . . . ?
N2 N1 C18 C23 -116.8(3) . . . . ?
N2 C3 C4 C5 177.3(3) . . . . ?
C1 N1 N2 C3 0.0(3) . . . . ?
C1 N1 C18 C19 -124.1(3) . . . . ?
C1 N1 C18 C23 57.5(4) . . . . ?
C1 C2 C3 N2 0.9(3) . . . . ?
C1 C2 C3 C4 -177.2(3) . . . . ?
C1 C12 C13 C14 -178.5(2) . . . . ?
C1 C12 C17 C16 178.9(3) . . . . ?
C2 C1 C12 C13 33.8(4) . . . . ?
C2 C1 C12 C17 -143.5(3) . . . . ?
C2 C3 C4 C5 -4.7(5) . . . . ?
C3 C4 C5 C6 -178.3(3) . . . . ?
C4 C5 C6 C7 161.1(3) . . . . ?
C4 C5 C6 C11 -17.0(5) . . . . ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C5 C6 C11 C10 177.3(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C7 C6 C11 C10 -0.9(4) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C6 -0.2(4) . . . . ?
C11 C6 C7 C8 1.3(4) . . . . ?
C12 C1 C2 C3 174.3(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C12 C17 C16 1.5(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
C18 N1 N2 C3 175.1(2) . . . . ?
C18 N1 C1 C2 -173.9(3) . . . . ?
C18 N1 C1 C12 10.6(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C18 C23 C22 -0.8(4) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C18 0.1(4) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?
N1A N2A C3A C2A 0.3(3) . . . . ?
N1A N2A C3A C4A -177.0(2) . . . . ?
N1A C1A C2A C3A -1.1(3) . . . . ?
N1A C1A C12A C13A -116.3(3) . . . . ?
N1A C1A C12A C17A 62.4(4) . . . . ?
N1A C18A C19A C20A 178.6(2) . . . . ?
N1A C18A C23A C22A -178.2(2) . . . . ?
N2A N1A C1A C2A 1.3(3) . . . . ?
N2A N1A C1A C12A 180.0(2) . . . . ?
N2A N1A C18A C19A -143.0(3) . . . . ?
N2A N1A C18A C23A 34.2(3) . . . . ?
N2A C3A C4A C5A 162.1(3) . . . . ?
C1A N1A N2A C3A -1.0(3) . . . . ?
C1A N1A C18A C19A 32.5(4) . . . . ?
C1A N1A C18A C23A -150.3(3) . . . . ?
C1A C2A C3A N2A 0.4(3) . . . . ?
C1A C2A C3A C4A 177.1(3) . . . . ?
C1A C12A C13A C14A 177.8(3) . . . . ?
C1A C12A C17A C16A -178.2(2) . . . . ?
C2A C1A C12A C13A 62.1(4) . . . . ?
C2A C1A C12A C17A -119.2(3) . . . . ?
C2A C3A C4A C5A -14.5(6) . . . . ?
C3A C4A C5A C6A -179.0(3) . . . . ?
C4A C5A C6A C7A -177.5(3) . . . . ?
C4A C5A C6A C11A 1.0(5) . . . . ?
C5A C6A C7A C8A 177.4(3) . . . . ?
C5A C6A C11A C10A -177.6(3) . . . . ?
C6A C7A C8A C9A 0.4(5) . . . . ?
C7A C6A C11A C10A 0.9(5) . . . . ?
C7A C8A C9A C10A 0.8(5) . . . . ?
C8A C9A C10A C11A -1.1(6) . . . . ?
C9A C10A C11A C6A 0.2(5) . . . . ?
C11A C6A C7A C8A -1.2(4) . . . . ?
C12A C1A C2A C3A -179.6(3) . . . . ?
C12A C13A C14A C15A 0.6(4) . . . . ?
C13A C12A C17A C16A 0.5(4) . . . . ?
C13A C14A C15A C16A 0.3(4) . . . . ?
C14A C15A C16A C17A -0.7(4) . . . . ?
C15A C16A C17A C12A 0.4(4) . . . . ?
C17A C12A C13A C14A -1.0(4) . . . . ?
C18A N1A N2A C3A 175.2(2) . . . . ?
C18A N1A C1A C2A -174.4(3) . . . . ?
C18A N1A C1A C12A 4.2(4) . . . . ?
C18A C19A C20A C21A -0.8(4) . . . . ?
C19A C18A C23A C22A -1.0(4) . . . . ?
C19A C20A C21A C22A -0.5(4) . . . . ?
C20A C21A C22A C23A 1.0(4) . . . . ?
C21A C22A C23A C18A -0.3(4) . . . . ?
C23A C18A C19A C20A 1.5(4) . . . . ?
