#------------------------------------------------------------------------------
#$Date: 2020-12-10 04:35:47 +0100 (jue 10 de dic de 2020) $
#$Revision: 259731 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/17/7241736.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_7241736
loop_
_publ_author_name
'Ye, Yang'
'Gao, Lei'
'Hao, Hongxun'
'Yin, Qiuxiang'
'Xie, Chuang'
_publ_section_title
;
 Tuning the photomechanical behavior and excellent elasticity of
 azobenzene via cocrystal engineering
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8045
_journal_page_last               8053
_journal_paper_doi               10.1039/D0CE01394C
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '2(C6 H8 N2), 2(C12 H11 N3)'
_chemical_formula_sum            'C36 H38 N10'
_chemical_formula_weight         610.76
_chemical_melting_point          352.5
_chemical_name_systematic        '4-Aminoazobenzene; 3-Amino-4-methylpyridine'
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-10 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.524(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8699(2)
_cell_length_b                   36.0925(7)
_cell_length_c                   11.3684(3)
_cell_measurement_reflns_used    24091
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      33.5000
_cell_measurement_theta_min      1.8060
_cell_volume                     3226.00(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku,2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00  90.00  180
  3  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0180892000
_diffrn_orient_matrix_UB_12      0.0165818000
_diffrn_orient_matrix_UB_13      -0.0316026000
_diffrn_orient_matrix_UB_21      0.0043673000
_diffrn_orient_matrix_UB_22      0.0101299000
_diffrn_orient_matrix_UB_23      0.0534993000
_diffrn_orient_matrix_UB_31      0.0883043000
_diffrn_orient_matrix_UB_32      0.0028926000
_diffrn_orient_matrix_UB_33      -0.0063097000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28712
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.880
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_preparation       photochromic
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/n-heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5896
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0467
_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)+(0.0613P)²+1.5782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5089
_reflns_number_total             5896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01394c3.cif
_cod_data_source_block           r20191214d
_cod_database_code               7241736
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.988
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3A = N3-H3B
 0.9 with sigma of 0.01
 H3B-H3A
 1.5 with sigma of 0.01
3. Others
 Fixed Sof: N9(0.6) N10(0.6) N9'(0.4) N10'(0.4)
4.a Rotating group:
 N1(H1A,H1B), N5(H5A,H5B), N8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
4.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.587
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.0723(2) 0.46824(4) 0.41060(14) 0.0403(4) Uani 1 1 d . . . . .
H1A H -0.002189 0.479570 0.366078 0.048 Uiso 1 1 d GR . . . .
H1B H 0.032615 0.465079 0.479319 0.048 Uiso 1 1 d GR . . . .
N2 N 0.07347(18) 0.36759(4) 0.36866(12) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.2670(2) 0.46513(5) 0.20128(16) 0.0434(4) Uani 1 1 d . . . . .
H1C H 0.347223 0.477580 0.256515 0.065 Uiso 1 1 calc GR . . . .
H1D H 0.173223 0.482008 0.179533 0.065 Uiso 1 1 calc GR . . . .
H1E H 0.325623 0.457968 0.130492 0.065 Uiso 1 1 calc GR . . . .
C2 C 0.1976(2) 0.43111(5) 0.25852(14) 0.0302(4) Uani 1 1 d . . . . .
C3 C 0.2203(2) 0.39595(5) 0.21331(14) 0.0339(4) Uani 1 1 d . . . . .
H3 H 0.279422 0.392962 0.142845 0.041 Uiso 1 1 calc R . . . .
C4 C 0.1583(2) 0.36519(5) 0.26920(15) 0.0353(4) Uani 1 1 d . . . . .
H4 H 0.176382 0.341432 0.236026 0.042 Uiso 1 1 calc R . . . .
C5 C 0.0488(2) 0.40151(4) 0.41173(14) 0.0309(4) Uani 1 1 d . . . . .
H5 H -0.012812 0.403550 0.481440 0.037 Uiso 1 1 calc R . . . .
C6 C 0.1070(2) 0.43412(4) 0.36167(14) 0.0285(3) Uani 1 1 d . . . . .
N3 N 0.26771(18) 0.63497(4) 0.28403(12) 0.0342(3) Uani 1 1 d D . . . .
N4 N 0.2708(2) 0.54249(4) 0.41946(14) 0.0422(4) Uani 1 1 d . . . . .
C7 C 0.4779(2) 0.65113(5) 0.49315(17) 0.0448(5) Uani 1 1 d . . . . .
H7A H 0.526483 0.651751 0.573998 0.067 Uiso 1 1 calc GR . . . .
H7B H 0.387082 0.669622 0.484293 0.067 Uiso 1 1 calc GR . . . .
H7C H 0.566946 0.656712 0.438173 0.067 Uiso 1 1 calc GR . . . .
C8 C 0.4065(2) 0.61338(5) 0.46711(14) 0.0327(4) Uani 1 1 d . . . . .
C9 C 0.4315(2) 0.58386(6) 0.54460(16) 0.0416(4) Uani 1 1 d . . . . .
H9 H 0.496023 0.587406 0.616303 0.050 Uiso 1 1 calc R . . . .
C10 C 0.3634(2) 0.54951(6) 0.51832(17) 0.0456(5) Uani 1 1 d . . . . .
H10 H 0.383208 0.529911 0.573003 0.055 Uiso 1 1 calc R . . . .
C11 C 0.2462(2) 0.57078(5) 0.34434(15) 0.0341(4) Uani 1 1 d . . . . .
H11 H 0.181419 0.566194 0.273360 0.041 Uiso 1 1 calc R . . . .
C12 C 0.30933(19) 0.60648(4) 0.36320(14) 0.0285(3) Uani 1 1 d . . . . .
N5 N -0.00988(19) 0.31219(4) 0.55270(13) 0.0364(3) Uani 1 1 d . . . . .
H5A H -0.021081 0.325648 0.488269 0.044 Uiso 1 1 d GR . . . .
H5B H -0.097715 0.315958 0.596497 0.044 Uiso 1 1 d GR . . . .
N6 N 0.03479(16) 0.16216(3) 0.43816(11) 0.0266(3) Uani 1 1 d . . . . .
N7 N 0.11981(16) 0.15372(3) 0.34998(11) 0.0270(3) Uani 1 1 d . . . . .
C13 C -0.04994(19) 0.21084(4) 0.56524(13) 0.0274(3) Uani 1 1 d . . . . .
H13 H -0.090970 0.192277 0.615981 0.033 Uiso 1 1 calc R . . . .
C14 C -0.0642(2) 0.24758(4) 0.59579(13) 0.0279(3) Uani 1 1 d . . . . .
H14 H -0.115770 0.254043 0.666937 0.034 Uiso 1 1 calc R . . . .
C15 C -0.00327(19) 0.27564(4) 0.52297(13) 0.0265(3) Uani 1 1 d . . . . .
C16 C 0.0696(2) 0.26498(4) 0.41696(14) 0.0279(3) Uani 1 1 d . . . . .
H16 H 0.110957 0.283480 0.366082 0.033 Uiso 1 1 calc R . . . .
C17 C 0.08192(19) 0.22836(4) 0.38611(13) 0.0263(3) Uani 1 1 d . . . . .
H17 H 0.129975 0.221818 0.313771 0.032 Uiso 1 1 calc R . . . .
C18 C 0.02399(18) 0.20045(4) 0.46066(13) 0.0244(3) Uani 1 1 d . . . . .
C19 C 0.13190(19) 0.11496(4) 0.32809(13) 0.0261(3) Uani 1 1 d . . . . .
C20 C 0.2096(2) 0.10538(4) 0.22450(14) 0.0318(4) Uani 1 1 d . . . . .
H20 H 0.247122 0.124254 0.173520 0.038 Uiso 1 1 calc R . . . .
C21 C 0.2323(2) 0.06844(5) 0.19547(16) 0.0361(4) Uani 1 1 d . . . . .
H21 H 0.284999 0.062032 0.124678 0.043 Uiso 1 1 calc R . . . .
C22 C 0.1781(2) 0.04094(5) 0.26987(16) 0.0366(4) Uani 1 1 d . . . . .
H22 H 0.193647 0.015612 0.250300 0.044 Uiso 1 1 calc R . . . .
C23 C 0.1009(2) 0.05039(4) 0.37308(15) 0.0347(4) Uani 1 1 d . . . . .
H23 H 0.063896 0.031368 0.423762 0.042 Uiso 1 1 calc R . . . .
C24 C 0.0769(2) 0.08712(4) 0.40332(14) 0.0290(3) Uani 1 1 d . . . . .
H24 H 0.023861 0.093355 0.474130 0.035 Uiso 1 1 calc R . . . .
N8 N 0.47195(17) 0.18959(3) 0.32402(12) 0.0283(3) Uani 1 1 d . . . . .
H8A H 0.502097 0.188679 0.397643 0.034 Uiso 1 1 d GR . . . .
H8B H 0.365857 0.184069 0.314933 0.034 Uiso 1 1 d GR . . . .
C25 C 0.6419(2) 0.28378(5) 0.29599(18) 0.0400(4) Uani 1 1 d . . . . .
H25 H 0.721937 0.299564 0.335914 0.048 Uiso 1 1 calc R . . . .
C26 C 0.6151(2) 0.24889(4) 0.33886(14) 0.0288(3) Uani 1 1 d . . . . .
H26 H 0.677295 0.240706 0.407552 0.035 Uiso 1 1 calc R . . . .
C27 C 0.49693(18) 0.22521(4) 0.28218(13) 0.0227(3) Uani 1 1 d . . . . .
C28 C 0.4086(2) 0.23765(5) 0.18017(14) 0.0321(4) Uani 1 1 d . . . . .
H28 H 0.328998 0.221811 0.140001 0.039 Uiso 1 1 calc R . . . .
C29 C 0.4367(2) 0.27294(6) 0.13759(17) 0.0455(5) Uani 1 1 d . . . . .
H29 H 0.375770 0.281284 0.068607 0.055 Uiso 1 1 calc R . . . .
C30 C 0.5547(3) 0.29643(5) 0.1959(2) 0.0471(5) Uani 1 1 d . . . . .
C31 C 0.6277(2) 0.38524(5) 0.0792(2) 0.0442(5) Uani 1 1 d . . . . .
C32 C 0.5538(2) 0.39995(5) -0.02241(19) 0.0462(5) Uani 1 1 d . . . . .
H32 H 0.482656 0.385003 -0.072631 0.055 Uiso 1 1 calc R . . . .
C33 C 0.5832(2) 0.43634(6) -0.05099(16) 0.0421(4) Uani 1 1 d . . . . .
H33 H 0.531693 0.446538 -0.120884 0.051 Uiso 1 1 calc R . . . .
C34 C 0.6865(2) 0.45799(5) 0.02099(17) 0.0374(4) Uani 1 1 d . . . . .
H34 H 0.704586 0.483256 0.001723 0.045 Uiso 1 1 calc R . . . .
C35 C 0.7639(2) 0.44312(5) 0.12105(17) 0.0413(4) Uani 1 1 d . . . . .
H35 H 0.837691 0.457972 0.169720 0.050 Uiso 1 1 calc R . . . .
C36 C 0.7348(3) 0.40680(5) 0.15086(16) 0.0438(5) Uani 1 1 d . . . . .
H36 H 0.787800 0.396561 0.220177 0.053 Uiso 1 1 calc R . . . .
N9 N 0.6136(4) 0.33482(10) 0.1826(3) 0.0256(7) Uani 0.6 1 d . . P A 1
N10 N 0.5661(3) 0.34693(8) 0.0822(2) 0.0254(5) Uani 0.6 1 d . . P A 1
N9' N 0.5402(5) 0.32768(12) 0.1126(4) 0.0254(7) Uani 0.4 1 d . . P A 2
N10' N 0.6372(6) 0.35109(13) 0.1611(5) 0.0278(11) Uani 0.4 1 d . . P A 2
H3A H 0.217(2) 0.6267(5) 0.2165(12) 0.050(6) Uiso 1 1 d D . . . .
H3B H 0.350(2) 0.6517(5) 0.2722(17) 0.059(6) Uiso 1 1 d D . . . .
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
H1A N1 H1B 109.4 . . ?
C6 N1 H1A 109.1 . . ?
C6 N1 H1B 109.4 . . ?
C5 N2 C4 117.00(14) . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C3 C2 C1 122.20(15) . . ?
C3 C2 C6 117.39(15) . . ?
C6 C2 C1 120.41(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.87(15) . . ?
C4 C3 H3 119.6 . . ?
N2 C4 C3 122.40(15) . . ?
N2 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
N2 C5 H5 117.7 . . ?
N2 C5 C6 124.66(15) . . ?
C6 C5 H5 117.7 . . ?
N1 C6 C2 121.43(15) . . ?
N1 C6 C5 120.89(15) . . ?
C5 C6 C2 117.66(15) . . ?
C12 N3 H3A 112.8(12) . . ?
C12 N3 H3B 116.1(13) . . ?
H3A N3 H3B 112.9(13) . . ?
C10 N4 C11 116.72(16) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
C9 C8 C7 122.02(16) . . ?
C9 C8 C12 117.03(16) . . ?
C12 C8 C7 120.94(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.61(17) . . ?
C10 C9 H9 119.7 . . ?
N4 C10 C9 123.03(17) . . ?
N4 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N4 C11 H11 117.8 . . ?
N4 C11 C12 124.48(16) . . ?
C12 C11 H11 117.8 . . ?
N3 C12 C8 121.11(15) . . ?
C11 C12 N3 120.65(15) . . ?
C11 C12 C8 118.12(15) . . ?
H5A N5 H5B 109.5 . . ?
C15 N5 H5A 109.3 . . ?
C15 N5 H5B 109.2 . . ?
N7 N6 C18 114.70(12) . . ?
N6 N7 C19 114.58(12) . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C18 120.98(14) . . ?
C18 C13 H13 119.5 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.78(14) . . ?
C15 C14 H14 119.6 . . ?
N5 C15 C14 122.24(14) . . ?
N5 C15 C16 119.80(14) . . ?
C14 C15 C16 117.95(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.12(14) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.53(14) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 N6 116.64(13) . . ?
C13 C18 C17 118.61(14) . . ?
C17 C18 N6 124.74(14) . . ?
C20 C19 N7 115.23(13) . . ?
C20 C19 C24 119.79(15) . . ?
C24 C19 N7 124.96(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.36(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.84(16) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.94(16) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.98(15) . . ?
C24 C23 H23 119.5 . . ?
C19 C24 H24 120.5 . . ?
C23 C24 C19 119.10(15) . . ?
C23 C24 H24 120.5 . . ?
H8A N8 H8B 109.4 . . ?
C27 N8 H8A 109.4 . . ?
C27 N8 H8B 109.0 . . ?
C26 C25 H25 119.4 . . ?
C26 C25 C30 121.26(17) . . ?
C30 C25 H25 119.4 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.45(16) . . ?
C27 C26 H26 119.8 . . ?
N8 C27 C26 120.61(14) . . ?
N8 C27 C28 120.56(14) . . ?
C26 C27 C28 118.79(14) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.26(16) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.27(17) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 118.96(16) . . ?
C25 C30 N9 104.4(2) . . ?
C25 C30 N9' 143.6(2) . . ?
C29 C30 N9 136.6(2) . . ?
C29 C30 N9' 97.4(2) . . ?
C32 C31 C36 120.04(16) . . ?
C32 C31 N10 104.77(19) . . ?
C32 C31 N10' 145.2(3) . . ?
C36 C31 N10 135.2(2) . . ?
C36 C31 N10' 94.7(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.83(17) . . ?
C33 C32 H32 120.1 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.29(17) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.01(16) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.21(17) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 H36 120.2 . . ?
C35 C36 C31 119.60(17) . . ?
C35 C36 H36 120.2 . . ?
N10 N9 C30 109.7(4) . . ?
N9 N10 C31 105.2(3) . . ?
N10' N9' C30 101.8(5) . . ?
N9' N10' C31 105.1(5) . . ?
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 H1A 0.8608 . ?
N1 H1B 0.8616 . ?
N1 C6 1.383(2) . ?
N2 C4 1.341(2) . ?
N2 C5 1.336(2) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 C2 1.503(2) . ?
C2 C3 1.384(2) . ?
C2 C6 1.403(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
N3 C12 1.396(2) . ?
N3 H3A 0.899(9) . ?
N3 H3B 0.903(9) . ?
N4 C10 1.337(2) . ?
N4 C11 1.339(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.498(2) . ?
C8 C9 1.391(3) . ?
C8 C12 1.401(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
N5 H5A 0.8801 . ?
N5 H5B 0.8801 . ?
N5 C15 1.363(2) . ?
N6 N7 1.2667(18) . ?
N6 C18 1.4086(19) . ?
N7 C19 1.4249(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(2) . ?
C13 C18 1.398(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(2) . ?
C15 C16 1.411(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.405(2) . ?
C19 C20 1.394(2) . ?
C19 C24 1.400(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(2) . ?
C24 H24 0.9500 . ?
N8 H8A 0.8604 . ?
N8 H8B 0.8602 . ?
N8 C27 1.3879(19) . ?
C25 H25 0.9500 . ?
C25 C26 1.370(2) . ?
C25 C30 1.381(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.399(2) . ?
C27 C28 1.400(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.402(3) . ?
C30 N9 1.471(4) . ?
C30 N9' 1.474(5) . ?
C31 C32 1.377(3) . ?
C31 C36 1.385(3) . ?
C31 N10 1.466(4) . ?
C31 N10' 1.545(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.375(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.372(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.376(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.376(3) . ?
C36 H36 0.9500 . ?
N9 N10 1.263(4) . ?
N9' N10' 1.251(7) . ?
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
N2 C5 C6 N1 178.46(16) . . . . ?
N2 C5 C6 C2 0.2(3) . . . . ?
C1 C2 C3 C4 178.60(16) . . . . ?
C1 C2 C6 N1 2.9(2) . . . . ?
C1 C2 C6 C5 -178.79(15) . . . . ?
C2 C3 C4 N2 0.2(3) . . . . ?
C3 C2 C6 N1 -177.42(15) . . . . ?
C3 C2 C6 C5 0.9(2) . . . . ?
C4 N2 C5 C6 -1.0(2) . . . . ?
C5 N2 C4 C3 0.8(2) . . . . ?
C6 C2 C3 C4 -1.0(2) . . . . ?
N4 C11 C12 N3 -175.49(16) . . . . ?
N4 C11 C12 C8 0.6(3) . . . . ?
C7 C8 C9 C10 179.69(17) . . . . ?
C7 C8 C12 N3 -3.7(2) . . . . ?
C7 C8 C12 C11 -179.86(16) . . . . ?
C8 C9 C10 N4 -0.3(3) . . . . ?
C9 C8 C12 N3 175.55(15) . . . . ?
C9 C8 C12 C11 -0.6(2) . . . . ?
C10 N4 C11 C12 -0.5(3) . . . . ?
C11 N4 C10 C9 0.3(3) . . . . ?
C12 C8 C9 C10 0.4(3) . . . . ?
N5 C15 C16 C17 178.36(14) . . . . ?
N6 N7 C19 C20 173.55(13) . . . . ?
N6 N7 C19 C24 -8.3(2) . . . . ?
N7 N6 C18 C13 -172.19(13) . . . . ?
N7 N6 C18 C17 7.7(2) . . . . ?
N7 C19 C20 C21 178.36(14) . . . . ?
N7 C19 C24 C23 -178.07(14) . . . . ?
C13 C14 C15 N5 -177.59(15) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C13 C18 N6 179.13(14) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 N6 -178.39(14) . . . . ?
C16 C17 C18 C13 1.5(2) . . . . ?
C18 N6 N7 C19 179.43(12) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C19 0.0(2) . . . . ?
C24 C19 C20 C21 0.1(2) . . . . ?
N8 C27 C28 C29 -178.67(14) . . . . ?
C25 C26 C27 N8 178.72(14) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C25 C30 N9 N10 168.0(2) . . . . ?
C25 C30 N9' N10' -7.3(5) . . . . ?
C26 C25 C30 C29 0.1(3) . . . . ?
C26 C25 C30 N9 177.79(18) . . . . ?
C26 C25 C30 N9' -175.0(3) . . . . ?
C26 C27 C28 C29 -0.9(2) . . . . ?
C27 C28 C29 C30 0.4(2) . . . . ?
C28 C29 C30 C25 0.0(3) . . . . ?
C28 C29 C30 N9 -176.8(2) . . . . ?
C28 C29 C30 N9' 177.03(19) . . . . ?
C29 C30 N9 N10 -14.9(4) . . . . ?
C29 C30 N9' N10' 177.1(3) . . . . ?
C30 C25 C26 C27 -0.5(2) . . . . ?
C30 N9 N10 C31 178.84(18) . . . . ?
C30 N9' N10' C31 -179.4(2) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C31 C36 C35 1.3(3) . . . . ?
C32 C31 N10 N9 -171.1(2) . . . . ?
C32 C31 N10' N9' 2.0(6) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C33 C34 C35 C36 -1.6(3) . . . . ?
C34 C35 C36 C31 0.3(3) . . . . ?
C36 C31 C32 C33 -1.6(3) . . . . ?
C36 C31 N10 N9 9.3(3) . . . . ?
C36 C31 N10' N9' 177.7(3) . . . . ?
N10 C31 C32 C33 178.74(17) . . . . ?
N10 C31 C36 C35 -179.2(2) . . . . ?
N10' C31 C32 C33 173.5(4) . . . . ?
N10' C31 C36 C35 -175.9(2) . . . . ?
