#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:56:43 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241579.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_7241579
loop_
_publ_author_name
'Han, Yanning'
'Zhang, Tong'
'Chen, Xinyu'
'Chen, Qiao'
'Xue, Pengchong'
_publ_section_title
;
 Spacer group-controlled luminescence and response of C3-symmetric
 triphenylamine derivatives towards force stimuli
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              202
_journal_page_last               209
_journal_paper_doi               10.1039/D0CE01539C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C45 H30 N4'
_chemical_formula_sum            'C45 H30 N4'
_chemical_formula_weight         626.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-12-21 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2313(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4053(2)
_cell_length_b                   32.0280(6)
_cell_length_c                   10.37836(18)
_cell_measurement_reflns_used    6693
_cell_measurement_temperature    136(1)
_cell_measurement_theta_max      73.5640
_cell_measurement_theta_min      2.7060
_cell_volume                     3453.20(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      136(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  29.00   1.00    5.87    --  -41.61  38.00-120.00   81
  2  ω   -107.00 -22.00   1.00    5.87    --  -41.61 -38.00 -90.00   85
  3  ω    -48.00  28.00   1.00    5.87    --  -41.61  77.00  30.00   76
  4  ω     37.00 132.00   1.00   28.48    --  107.08 -45.00  90.00   95
  5  ω     79.00 173.00   1.00   28.48    --  107.08  30.00 -90.00   94
  6  ω    107.00 178.00   1.00   28.48    --  107.08 125.00-150.00   71
  7  ω     94.00 173.00   1.00   28.48    --  107.08 125.00 150.00   79
  8  ω     24.00  50.00   1.00   28.48    --  107.08 -94.00 150.00   26
  9  ω     56.00  96.00   1.00   28.48    --  107.08 -94.00 150.00   40
 10  ω     46.00 103.00   1.00   28.48    --  107.08 -94.00 -90.00   57
 11  ω     85.00 110.00   1.00   28.48    --  107.08 -94.00 -90.00   25
 12  ω    -77.00 -48.00   1.00    5.87    --  -41.74 -38.00-150.00   29
 13  ω     27.00  75.00   1.00    5.87    --   41.74  38.00  30.00   48
 14  ω      1.00  39.00   1.00    5.87    --   41.74 -99.00 150.00   38
 15  ω     52.00  78.00   1.00    5.87    --   41.74  57.00  30.00   26
 16  ω     25.00  84.00   1.00    5.87    --   41.74  57.00  60.00   59
 17  ω    109.00 166.00   1.00   28.48    --  107.08  77.00 -60.00   57
 18  ω     75.00 101.00   1.00   28.48    --  107.08  77.00  30.00   26
 19  ω     75.00 104.00   1.00   28.48    --  107.08  77.00 -60.00   29
 20  ω     78.00 130.00   1.00   28.48    --  107.08  61.00   0.00   52
 21  ω     78.00 103.00   1.00   28.48    --  107.08  61.00  30.00   25
 22  ω    127.00 176.00   1.00   28.48    --  107.08  77.00   0.00   49
 23  ω     79.00 104.00   1.00   28.48    --  107.08  61.00 -30.00   25
 24  ω     76.00 102.00   1.00   28.48    --  107.08  77.00  60.00   26
 25  ω     74.00 125.00   1.00   28.48    --  107.08  77.00 -30.00   51
 26  ω    128.00 164.00   1.00   28.48    --  107.08  45.00  60.00   36
 27  ω     81.00 109.00   1.00   28.48    --  107.08  45.00  60.00   28
 28  ω     82.00 107.00   1.00   28.48    --  107.08  45.00   0.00   25
 29  ω     83.00 127.00   1.00   28.48    --  107.08  45.00  30.00   44
 30  ω     81.00 109.00   1.00   28.48    --  107.08  45.00  90.00   28
 31  ω     74.00  99.00   1.00   28.48    --  107.08  77.00   0.00   25
 32  ω     86.00 112.00   1.00   28.48    --  107.08  30.00  90.00   26
 33  ω     79.00 105.00   1.00   28.48    --  107.08  61.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057945000
_diffrn_orient_matrix_UB_12      0.0204593000
_diffrn_orient_matrix_UB_13      0.1345443000
_diffrn_orient_matrix_UB_21      0.1438093000
_diffrn_orient_matrix_UB_22      0.0096999000
_diffrn_orient_matrix_UB_23      -0.0122653000
_diffrn_orient_matrix_UB_31      -0.0357599000
_diffrn_orient_matrix_UB_32      0.0424350000
_diffrn_orient_matrix_UB_33      -0.0620517000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14386
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        67.047
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32716
_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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1139P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_full    0.571
_reflns_Friedel_fraction_max     0.571
_reflns_number_gt                4402
_reflns_number_total             4849
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01539c2.cif
_cod_data_source_block           a191125a
_cod_depositor_comments          'Adding full bibliography for 7241579.cif.'
_cod_original_cell_volume        3453.19(12)
_cod_database_code               7241579
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C28(H28), C29(H29), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-11-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.533
_oxdiff_exptl_absorpt_empirical_full_min 0.194
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'
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 0.7173(3) 0.76890(11) 0.7773(3) 0.0229(7) Uani 1 1 d . . . . .
N2 N -0.1451(5) 1.00100(16) 1.3676(5) 0.0467(12) Uani 1 1 d . . . . .
N3 N 1.1453(5) 0.40541(13) 1.2677(4) 0.0397(10) Uani 1 1 d . . . . .
N4 N 1.0537(5) 0.91035(15) -0.3676(4) 0.0424(10) Uani 1 1 d . . . . .
C1 C 0.6291(4) 0.79331(12) 0.8473(4) 0.0205(8) Uani 1 1 d . . . . .
C2 C 0.5254(4) 0.81328(13) 0.7826(4) 0.0240(9) Uani 1 1 d . . . . .
H2 H 0.5114 0.8101 0.6939 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4430(4) 0.83792(14) 0.8507(4) 0.0247(9) Uani 1 1 d . . . . .
H3 H 0.3749 0.8515 0.8068 0.030 Uiso 1 1 calc R . . . .
C4 C 0.4610(4) 0.84259(13) 0.9840(4) 0.0224(8) Uani 1 1 d . . . . .
C5 C 0.5636(4) 0.82176(13) 1.0479(4) 0.0235(8) Uani 1 1 d . . . . .
H5 H 0.5765 0.8243 1.1369 0.028 Uiso 1 1 calc R . . . .
C6 C 0.6472(4) 0.79718(13) 0.9795(4) 0.0227(8) Uani 1 1 d . . . . .
H6 H 0.7152 0.7834 1.0232 0.027 Uiso 1 1 calc R . . . .
C7 C 0.3750(4) 0.86799(13) 1.0610(4) 0.0248(9) Uani 1 1 d . . . . .
H7 H 0.3772 0.8627 1.1492 0.030 Uiso 1 1 calc R . . . .
C8 C 0.2948(5) 0.89763(14) 1.0171(4) 0.0272(9) Uani 1 1 d . . . . .
H8 H 0.2956 0.9045 0.9301 0.033 Uiso 1 1 calc R . . . .
C9 C 0.2047(4) 0.92037(14) 1.0962(4) 0.0260(9) Uani 1 1 d . . . . .
C10 C 0.1720(5) 0.90551(15) 1.2161(5) 0.0304(10) Uani 1 1 d . . . . .
H10 H 0.2089 0.8809 1.2480 0.036 Uiso 1 1 calc R . . . .
C11 C 0.0851(5) 0.92692(16) 1.2892(5) 0.0319(10) Uani 1 1 d . . . . .
H11 H 0.0656 0.9171 1.3702 0.038 Uiso 1 1 calc R . . . .
C12 C 0.0274(4) 0.96335(15) 1.2392(5) 0.0299(10) Uani 1 1 d . . . . .
C13 C 0.0588(5) 0.97862(14) 1.1204(5) 0.0311(10) Uani 1 1 d . . . . .
H13 H 0.0213 1.0031 1.0881 0.037 Uiso 1 1 calc R . . . .
C14 C 0.1472(5) 0.95690(15) 1.0497(4) 0.0302(10) Uani 1 1 d . . . . .
H14 H 0.1680 0.9671 0.9696 0.036 Uiso 1 1 calc R . . . .
C15 C -0.0672(5) 0.98436(16) 1.3105(5) 0.0353(11) Uani 1 1 d . . . . .
C16 C 0.7744(4) 0.73311(12) 0.8363(4) 0.0196(8) Uani 1 1 d . . . . .
C17 C 0.6987(4) 0.70555(13) 0.9059(4) 0.0227(8) Uani 1 1 d . . . . .
H17 H 0.6117 0.7111 0.9134 0.027 Uiso 1 1 calc R . . . .
C18 C 0.7535(4) 0.67021(13) 0.9629(4) 0.0235(9) Uani 1 1 d . . . . .
H18 H 0.7026 0.6524 1.0092 0.028 Uiso 1 1 calc R . . . .
C19 C 0.8843(4) 0.66072(12) 0.9523(4) 0.0207(8) Uani 1 1 d . . . . .
C20 C 0.9586(4) 0.68905(13) 0.8855(4) 0.0218(8) Uani 1 1 d . . . . .
H20 H 1.0460 0.6839 0.8794 0.026 Uiso 1 1 calc R . . . .
C21 C 0.9048(4) 0.72442(13) 0.8283(4) 0.0222(8) Uani 1 1 d . . . . .
H21 H 0.9562 0.7426 0.7841 0.027 Uiso 1 1 calc R . . . .
C22 C 0.9442(4) 0.62236(13) 1.0036(4) 0.0236(8) Uani 1 1 d . . . . .
H22 H 1.0318 0.6191 0.9927 0.028 Uiso 1 1 calc R . . . .
C23 C 0.8861(4) 0.59167(13) 1.0641(4) 0.0266(9) Uani 1 1 d . . . . .
H23 H 0.7995 0.5953 1.0790 0.032 Uiso 1 1 calc R . . . .
C24 C 0.9470(4) 0.55265(13) 1.1094(4) 0.0241(9) Uani 1 1 d . . . . .
C25 C 0.8818(5) 0.52688(15) 1.1925(5) 0.0313(10) Uani 1 1 d . . . . .
H25 H 0.8020 0.5353 1.2192 0.038 Uiso 1 1 calc R . . . .
C26 C 0.9322(5) 0.48928(15) 1.2360(5) 0.0320(10) Uani 1 1 d . . . . .
H26 H 0.8880 0.4727 1.2923 0.038 Uiso 1 1 calc R . . . .
C27 C 1.0525(5) 0.47644(14) 1.1929(4) 0.0255(9) Uani 1 1 d . . . . .
C28 C 1.1191(5) 0.50185(15) 1.1102(5) 0.0327(10) Uani 1 1 d . . . . .
H28 H 1.1986 0.4935 1.0826 0.039 Uiso 1 1 calc R . . . .
C29 C 1.0662(5) 0.53939(15) 1.0697(5) 0.0308(10) Uani 1 1 d . . . . .
H29 H 1.1110 0.5563 1.0146 0.037 Uiso 1 1 calc R . . . .
C30 C 1.1042(5) 0.43701(15) 1.2340(5) 0.0309(10) Uani 1 1 d . . . . .
C31 C 0.7596(4) 0.78407(14) 0.6587(4) 0.0212(8) Uani 1 1 d . . . . .
C32 C 0.7935(4) 0.75610(13) 0.5621(4) 0.0233(9) Uani 1 1 d . . . . .
H32 H 0.7904 0.7275 0.5771 0.028 Uiso 1 1 calc R . . . .
C33 C 0.8314(4) 0.77091(14) 0.4447(4) 0.0247(9) Uani 1 1 d . . . . .
H33 H 0.8542 0.7520 0.3818 0.030 Uiso 1 1 calc R . . . .
C34 C 0.8360(4) 0.81365(13) 0.4191(4) 0.0216(8) Uani 1 1 d . . . . .
C35 C 0.8030(4) 0.84084(13) 0.5172(4) 0.0234(8) Uani 1 1 d . . . . .
H35 H 0.8056 0.8695 0.5025 0.028 Uiso 1 1 calc R . . . .
C36 C 0.7668(4) 0.82663(13) 0.6346(4) 0.0229(9) Uani 1 1 d . . . . .
H36 H 0.7470 0.8456 0.6983 0.027 Uiso 1 1 calc R . . . .
C37 C 0.8696(4) 0.83128(13) 0.2955(4) 0.0239(9) Uani 1 1 d . . . . .
H37 H 0.8558 0.8598 0.2856 0.029 Uiso 1 1 calc R . . . .
C38 C 0.9178(4) 0.81186(13) 0.1946(4) 0.0243(9) Uani 1 1 d . . . . .
H38 H 0.9355 0.7835 0.2018 0.029 Uiso 1 1 calc R . . . .
C39 C 0.9439(4) 0.83291(14) 0.0734(4) 0.0260(9) Uani 1 1 d . . . . .
C40 C 0.8878(5) 0.87153(14) 0.0384(4) 0.0264(9) Uani 1 1 d . . . . .
H40 H 0.8311 0.8840 0.0929 0.032 Uiso 1 1 calc R . . . .
C41 C 0.9148(5) 0.89130(14) -0.0745(4) 0.0278(9) Uani 1 1 d . . . . .
H41 H 0.8779 0.9170 -0.0953 0.033 Uiso 1 1 calc R . . . .
C42 C 0.9987(4) 0.87221(14) -0.1579(4) 0.0267(9) Uani 1 1 d . . . . .
C43 C 1.0512(5) 0.83342(15) -0.1267(5) 0.0317(10) Uani 1 1 d . . . . .
H43 H 1.1052 0.8205 -0.1829 0.038 Uiso 1 1 calc R . . . .
C44 C 1.0240(4) 0.81404(15) -0.0136(5) 0.0286(9) Uani 1 1 d . . . . .
H44 H 1.0594 0.7880 0.0057 0.034 Uiso 1 1 calc R . . . .
C45 C 1.0288(5) 0.89330(15) -0.2747(5) 0.0321(10) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C16 N1 C1 119.2(3) . . ?
C16 N1 C31 120.7(3) . . ?
C31 N1 C1 119.5(3) . . ?
C2 C1 N1 120.5(4) . . ?
C6 C1 N1 119.8(4) . . ?
C6 C1 C2 119.7(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 C7 123.0(4) . . ?
C5 C4 C7 118.6(4) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C7 H7 116.7 . . ?
C8 C7 C4 126.6(4) . . ?
C8 C7 H7 116.7 . . ?
C7 C8 H8 117.6 . . ?
C7 C8 C9 124.7(4) . . ?
C9 C8 H8 117.6 . . ?
C10 C9 C8 121.6(4) . . ?
C14 C9 C8 119.9(4) . . ?
C14 C9 C10 118.5(4) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.1(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C15 119.5(5) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 C15 119.9(4) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(4) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.4(4) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N2 C15 C12 179.1(6) . . ?
C17 C16 N1 119.7(4) . . ?
C21 C16 N1 121.6(4) . . ?
C21 C16 C17 118.7(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C22 123.2(4) . . ?
C20 C19 C18 117.6(4) . . ?
C20 C19 C22 119.2(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.7(4) . . ?
C20 C21 H21 119.6 . . ?
C19 C22 H22 116.7 . . ?
C23 C22 C19 126.6(4) . . ?
C23 C22 H22 116.7 . . ?
C22 C23 H23 117.2 . . ?
C22 C23 C24 125.6(4) . . ?
C24 C23 H23 117.2 . . ?
C25 C24 C23 119.0(4) . . ?
C29 C24 C23 122.6(4) . . ?
C29 C24 C25 118.3(4) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 121.9(4) . . ?
C26 C25 H25 119.0 . . ?
C25 C26 H26 120.7 . . ?
C25 C26 C27 118.5(4) . . ?
C27 C26 H26 120.7 . . ?
C26 C27 C30 119.2(4) . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 C30 120.5(4) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.5(5) . . ?
C29 C28 H28 120.2 . . ?
C24 C29 H29 119.3 . . ?
C28 C29 C24 121.4(4) . . ?
C28 C29 H29 119.3 . . ?
N3 C30 C27 179.5(6) . . ?
C32 C31 N1 120.3(4) . . ?
C36 C31 N1 121.1(4) . . ?
C36 C31 C32 118.6(4) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.4 . . ?
C32 C33 C34 121.1(4) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C35 117.4(4) . . ?
C33 C34 C37 123.9(4) . . ?
C35 C34 C37 118.6(4) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 C34 122.1(4) . . ?
C36 C35 H35 119.0 . . ?
C31 C36 H36 119.8 . . ?
C35 C36 C31 120.4(4) . . ?
C35 C36 H36 119.8 . . ?
C34 C37 H37 115.6 . . ?
C38 C37 C34 128.7(4) . . ?
C38 C37 H37 115.6 . . ?
C37 C38 H38 118.2 . . ?
C37 C38 C39 123.6(4) . . ?
C39 C38 H38 118.2 . . ?
C40 C39 C38 122.1(4) . . ?
C44 C39 C38 120.1(4) . . ?
C44 C39 C40 117.8(4) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 C39 121.6(4) . . ?
C41 C40 H40 119.2 . . ?
C40 C41 H41 120.4 . . ?
C40 C41 C42 119.3(4) . . ?
C42 C41 H41 120.4 . . ?
C41 C42 C45 119.2(4) . . ?
C43 C42 C41 119.7(4) . . ?
C43 C42 C45 121.1(4) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.5(4) . . ?
C44 C43 H43 119.8 . . ?
C39 C44 H44 119.5 . . ?
C43 C44 C39 121.1(4) . . ?
C43 C44 H44 119.5 . . ?
N4 C45 C42 179.4(6) . . ?
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 1.434(5) . ?
N1 C16 1.415(5) . ?
N1 C31 1.416(5) . ?
N2 C15 1.160(7) . ?
N3 C30 1.146(7) . ?
N4 C45 1.151(7) . ?
C1 C2 1.393(6) . ?
C1 C6 1.381(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(6) . ?
C4 C5 1.394(6) . ?
C4 C7 1.477(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.327(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.474(6) . ?
C9 C10 1.392(6) . ?
C9 C14 1.388(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.399(7) . ?
C12 C13 1.382(7) . ?
C12 C15 1.433(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(7) . ?
C14 H14 0.9300 . ?
C16 C17 1.409(6) . ?
C16 C21 1.392(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.405(6) . ?
C19 C20 1.401(6) . ?
C19 C22 1.464(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.330(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.467(6) . ?
C24 C25 1.397(7) . ?
C24 C29 1.396(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.414(7) . ?
C27 C28 1.395(7) . ?
C27 C30 1.428(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.378(7) . ?
C29 H29 0.9300 . ?
C31 C32 1.404(6) . ?
C31 C36 1.389(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.386(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.396(6) . ?
C34 C35 1.397(6) . ?
C34 C37 1.462(6) . ?
C35 H35 0.9300 . ?
C35 C36 1.373(6) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C37 C38 1.339(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.465(6) . ?
C39 C40 1.407(6) . ?
C39 C44 1.400(7) . ?
C40 H40 0.9300 . ?
C40 C41 1.374(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.404(6) . ?
C42 C43 1.388(7) . ?
C42 C45 1.437(6) . ?
C43 H43 0.9300 . ?
C43 C44 1.372(7) . ?
C44 H44 0.9300 . ?
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 C1 C2 C3 -177.9(4) . . . . ?
N1 C1 C6 C5 178.4(4) . . . . ?
N1 C16 C17 C18 179.4(3) . . . . ?
N1 C16 C21 C20 -179.3(4) . . . . ?
N1 C31 C32 C33 178.2(4) . . . . ?
N1 C31 C36 C35 -177.3(4) . . . . ?
C1 N1 C16 C17 43.3(6) . . . . ?
C1 N1 C16 C21 -136.3(4) . . . . ?
C1 N1 C31 C32 -150.6(4) . . . . ?
C1 N1 C31 C36 28.5(6) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C2 C1 C6 C5 -1.4(6) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C2 C3 C4 C7 -179.1(4) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C3 C4 C7 C8 -19.3(7) . . . . ?
C4 C5 C6 C1 0.1(7) . . . . ?
C4 C7 C8 C9 175.9(4) . . . . ?
C5 C4 C7 C8 161.8(4) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
C7 C4 C5 C6 179.6(4) . . . . ?
C7 C8 C9 C10 -16.9(7) . . . . ?
C7 C8 C9 C14 165.1(5) . . . . ?
C8 C9 C10 C11 -178.9(4) . . . . ?
C8 C9 C14 C13 178.3(4) . . . . ?
C9 C10 C11 C12 1.7(8) . . . . ?
C10 C9 C14 C13 0.2(7) . . . . ?
C10 C11 C12 C13 -1.8(7) . . . . ?
C10 C11 C12 C15 176.7(4) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
C12 C13 C14 C9 -0.3(7) . . . . ?
C14 C9 C10 C11 -0.9(7) . . . . ?
C15 C12 C13 C14 -177.4(5) . . . . ?
C16 N1 C1 C2 -146.6(4) . . . . ?
C16 N1 C1 C6 33.6(6) . . . . ?
C16 N1 C31 C32 38.4(6) . . . . ?
C16 N1 C31 C36 -142.5(4) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C17 C16 C21 C20 1.1(6) . . . . ?
C17 C18 C19 C20 2.1(6) . . . . ?
C17 C18 C19 C22 -175.8(4) . . . . ?
C18 C19 C20 C21 -2.0(6) . . . . ?
C18 C19 C22 C23 0.9(6) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C19 C22 C23 C24 177.0(4) . . . . ?
C20 C19 C22 C23 -177.0(4) . . . . ?
C21 C16 C17 C18 -1.1(6) . . . . ?
C22 C19 C20 C21 176.0(4) . . . . ?
C22 C23 C24 C25 167.9(4) . . . . ?
C22 C23 C24 C29 -14.2(7) . . . . ?
C23 C24 C25 C26 178.3(4) . . . . ?
C23 C24 C29 C28 -177.6(4) . . . . ?
C24 C25 C26 C27 -1.0(7) . . . . ?
C25 C24 C29 C28 0.2(7) . . . . ?
C25 C26 C27 C28 1.2(7) . . . . ?
C25 C26 C27 C30 -178.1(5) . . . . ?
C26 C27 C28 C29 -0.6(7) . . . . ?
C27 C28 C29 C24 -0.1(8) . . . . ?
C29 C24 C25 C26 0.4(7) . . . . ?
C30 C27 C28 C29 178.7(4) . . . . ?
C31 N1 C1 C2 42.3(6) . . . . ?
C31 N1 C1 C6 -137.5(4) . . . . ?
C31 N1 C16 C17 -145.7(4) . . . . ?
C31 N1 C16 C21 34.7(6) . . . . ?
C31 C32 C33 C34 -0.5(6) . . . . ?
C32 C31 C36 C35 1.8(6) . . . . ?
C32 C33 C34 C35 1.1(6) . . . . ?
C32 C33 C34 C37 -177.2(4) . . . . ?
C33 C34 C35 C36 -0.2(6) . . . . ?
C33 C34 C37 C38 -10.1(7) . . . . ?
C34 C35 C36 C31 -1.2(6) . . . . ?
C34 C37 C38 C39 178.0(4) . . . . ?
C35 C34 C37 C38 171.7(4) . . . . ?
C36 C31 C32 C33 -0.9(6) . . . . ?
C37 C34 C35 C36 178.1(4) . . . . ?
C37 C38 C39 C40 -18.8(7) . . . . ?
C37 C38 C39 C44 163.2(4) . . . . ?
C38 C39 C40 C41 178.9(4) . . . . ?
C38 C39 C44 C43 -179.1(4) . . . . ?
C39 C40 C41 C42 1.1(7) . . . . ?
C40 C39 C44 C43 2.7(7) . . . . ?
C40 C41 C42 C43 1.2(7) . . . . ?
C40 C41 C42 C45 -178.8(4) . . . . ?
C41 C42 C43 C44 -1.5(7) . . . . ?
C42 C43 C44 C39 -0.5(7) . . . . ?
C44 C39 C40 C41 -3.0(6) . . . . ?
C45 C42 C43 C44 178.6(4) . . . . ?
