#------------------------------------------------------------------------------
#$Date: 2021-07-17 03:49:31 +0300 (Sat, 17 Jul 2021) $
#$Revision: 267604 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/41/1564197.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_1564197
loop_
_publ_author_name
'Lai, Liming'
'Fang, Bing'
'Fan, Mingyu'
'Cheng, Wenyu'
'Yin, Meizhen'
_publ_section_title
;
 Modulating Room-Temperature Phosphorescence through the Synergistic
 Effect of Heavy-Atom Effect and Halogen Bonding
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.1c04989
_journal_year                    2021
_chemical_formula_moiety         'C19 H12 N2'
_chemical_formula_sum            'C19 H12 N2'
_chemical_formula_weight         268.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                91.552(5)
_cell_angle_beta                 91.094(6)
_cell_angle_gamma                104.842(5)
_cell_formula_units_Z            4
_cell_length_a                   8.1748(6)
_cell_length_b                   8.6077(4)
_cell_length_c                   20.3539(16)
_cell_measurement_reflns_used    2729
_cell_measurement_temperature    110(3)
_cell_measurement_theta_max      28.6890
_cell_measurement_theta_min      3.8320
_cell_volume                     1383.43(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8374
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -57.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   21.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   -4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   57.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   -8.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  150.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0787107000
_diffrn_orient_matrix_UB_12      0.0107741000
_diffrn_orient_matrix_UB_13      0.0171159000
_diffrn_orient_matrix_UB_21      0.0026303000
_diffrn_orient_matrix_UB_22      0.0819784000
_diffrn_orient_matrix_UB_23      0.0065312000
_diffrn_orient_matrix_UB_31      -0.0431348000
_diffrn_orient_matrix_UB_32      -0.0209402000
_diffrn_orient_matrix_UB_33      0.0296744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10724
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0891
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0378P)²+3.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2084
_reflns_number_gt                4279
_reflns_number_total             5417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp1c04989_si_002.cif
_cod_data_source_block           exp_6443
_cod_original_cell_volume        1383.44(16)
_cod_database_code               1564197
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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 1.0022(4) 0.9974(3) 0.37668(15) 0.0208(6) Uani 1 1 d . . .
N2 N 1.3776(5) 0.5523(5) 0.5694(2) 0.0542(12) Uani 1 1 d . . .
C1 C 0.9872(5) 1.3549(4) 0.29212(18) 0.0272(8) Uani 1 1 d . . .
H1 H 0.9037 1.3932 0.2713 0.033 Uiso 1 1 calc R . .
C2 C 1.1531(5) 1.4441(5) 0.29310(19) 0.0293(9) Uani 1 1 d . . .
H2 H 1.1816 1.5428 0.2730 0.035 Uiso 1 1 calc R . .
C3 C 1.2810(5) 1.3861(5) 0.32458(19) 0.0284(9) Uani 1 1 d . . .
H3 H 1.3927 1.4473 0.3249 0.034 Uiso 1 1 calc R . .
C4 C 1.2415(5) 1.2399(4) 0.35469(18) 0.0235(8) Uani 1 1 d . . .
H4 H 1.3256 1.2023 0.3753 0.028 Uiso 1 1 calc R . .
C5 C 1.0744(5) 1.1502(4) 0.35378(17) 0.0230(8) Uani 1 1 d . . .
C6 C 0.9448(5) 1.2074(4) 0.32232(17) 0.0239(8) Uani 1 1 d . . .
C7 C 0.7895(5) 1.0840(4) 0.32780(17) 0.0231(8) Uani 1 1 d . . .
C8 C 0.8278(5) 0.9559(4) 0.36146(17) 0.0226(8) Uani 1 1 d . . .
C9 C 0.7037(5) 0.8204(4) 0.37672(18) 0.0257(8) Uani 1 1 d . . .
H9 H 0.7310 0.7361 0.3983 0.031 Uiso 1 1 calc R . .
C10 C 0.5366(5) 0.8138(5) 0.35878(19) 0.0296(9) Uani 1 1 d . . .
H10 H 0.4507 0.7247 0.3692 0.035 Uiso 1 1 calc R . .
C11 C 0.4965(5) 0.9398(5) 0.3253(2) 0.0303(9) Uani 1 1 d . . .
H11 H 0.3845 0.9324 0.3132 0.036 Uiso 1 1 calc R . .
C12 C 0.6204(5) 1.0744(5) 0.31007(18) 0.0266(8) Uani 1 1 d . . .
H12 H 0.5923 1.1580 0.2883 0.032 Uiso 1 1 calc R . .
C13 C 1.0864(5) 0.9043(4) 0.41487(17) 0.0216(8) Uani 1 1 d . . .
C14 C 1.0540(5) 0.7390(4) 0.40160(18) 0.0240(8) Uani 1 1 d . . .
H14 H 0.9829 0.6913 0.3664 0.029 Uiso 1 1 calc R . .
C15 C 1.1286(5) 0.6464(4) 0.44124(19) 0.0250(8) Uani 1 1 d . . .
H15 H 1.1054 0.5359 0.4334 0.030 Uiso 1 1 calc R . .
C16 C 1.2381(5) 0.7192(4) 0.49271(18) 0.0247(8) Uani 1 1 d . . .
C17 C 1.2753(5) 0.8856(4) 0.50454(18) 0.0242(8) Uani 1 1 d . . .
H17 H 1.3521 0.9342 0.5379 0.029 Uiso 1 1 calc R . .
C18 C 1.1971(5) 0.9775(4) 0.46620(17) 0.0226(8) Uani 1 1 d . . .
H18 H 1.2183 1.0876 0.4747 0.027 Uiso 1 1 calc R . .
C19 C 1.3161(5) 0.6244(5) 0.5346(2) 0.0344(10) Uani 1 1 d . . .
N3 N 0.0235(4) 0.5242(3) 0.12344(15) 0.0232(7) Uani 1 1 d . . .
N4 N 0.3515(5) 0.0271(5) -0.0681(2) 0.0523(12) Uani 1 1 d . . .
C20 C 0.0350(5) 0.9015(4) 0.20614(18) 0.0264(8) Uani 1 1 d . . .
H20 H -0.0427 0.9455 0.2277 0.032 Uiso 1 1 calc R . .
C21 C 0.2009(5) 0.9888(5) 0.20224(19) 0.0302(9) Uani 1 1 d . . .
H21 H 0.2349 1.0924 0.2207 0.036 Uiso 1 1 calc R . .
C22 C 0.3189(5) 0.9217(5) 0.17040(19) 0.0280(9) Uani 1 1 d . . .
H22 H 0.4308 0.9816 0.1685 0.034 Uiso 1 1 calc R . .
C23 C 0.2723(5) 0.7689(4) 0.14189(18) 0.0252(8) Uani 1 1 d . . .
H23 H 0.3514 0.7255 0.1209 0.030 Uiso 1 1 calc R . .
C24 C 0.1027(5) 0.6803(4) 0.14526(17) 0.0225(8) Uani 1 1 d . . .
C25 C -0.0159(5) 0.7481(4) 0.17785(18) 0.0246(8) Uani 1 1 d . . .
C26 C -0.1751(5) 0.6252(4) 0.17423(17) 0.0247(8) Uani 1 1 d . . .
C27 C -0.3391(5) 0.6251(5) 0.19380(19) 0.0299(9) Uani 1 1 d . . .
H27 H -0.3598 0.7146 0.2153 0.036 Uiso 1 1 calc R . .
C28 C -0.4682(5) 0.4895(5) 0.1803(2) 0.0317(9) Uani 1 1 d . . .
H28 H -0.5768 0.4869 0.1939 0.038 Uiso 1 1 calc R . .
C29 C -0.4394(5) 0.3546(5) 0.1465(2) 0.0309(9) Uani 1 1 d . . .
H29 H -0.5296 0.2655 0.1371 0.037 Uiso 1 1 calc R . .
C30 C -0.2782(5) 0.3524(5) 0.12678(18) 0.0270(8) Uani 1 1 d . . .
H30 H -0.2585 0.2627 0.1051 0.032 Uiso 1 1 calc R . .
C31 C -0.1474(5) 0.4893(4) 0.14060(17) 0.0228(8) Uani 1 1 d . . .
C32 C 0.0967(5) 0.4199(4) 0.08508(17) 0.0222(8) Uani 1 1 d . . .
C33 C 0.0646(5) 0.2588(4) 0.09896(18) 0.0251(8) Uani 1 1 d . . .
H33 H -0.0009 0.2194 0.1347 0.030 Uiso 1 1 calc R . .
C34 C 0.1299(5) 0.1553(4) 0.05974(19) 0.0252(8) Uani 1 1 d . . .
H34 H 0.1047 0.0461 0.0680 0.030 Uiso 1 1 calc R . .
C35 C 0.2334(5) 0.2170(4) 0.00797(18) 0.0253(8) Uani 1 1 d . . .
C36 C 0.2705(5) 0.3790(4) -0.00467(18) 0.0252(8) Uani 1 1 d . . .
H36 H 0.3421 0.4198 -0.0386 0.030 Uiso 1 1 calc R . .
C37 C 0.2008(5) 0.4810(4) 0.03328(18) 0.0231(8) Uani 1 1 d . . .
H37 H 0.2235 0.5896 0.0242 0.028 Uiso 1 1 calc R . .
C38 C 0.3003(5) 0.1100(5) -0.0336(2) 0.0343(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 0.0033 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
C5 N1 C8 108.9(3) . . ?
C5 N1 C13 126.0(3) . . ?
C8 N1 C13 124.8(3) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(4) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C6 108.5(3) . . ?
C4 C5 N1 130.6(3) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 C7 133.8(4) . . ?
C5 C6 C7 106.7(3) . . ?
C8 C7 C6 107.7(3) . . ?
C12 C7 C6 133.2(3) . . ?
C12 C7 C8 119.0(3) . . ?
N1 C8 C7 108.2(3) . . ?
C9 C8 N1 129.8(3) . . ?
C9 C8 C7 121.9(3) . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.2(4) . . ?
C11 C12 H12 120.4 . . ?
C14 C13 N1 119.5(3) . . ?
C18 C13 N1 119.9(3) . . ?
C18 C13 C14 120.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 C19 120.5(3) . . ?
C17 C16 C19 118.9(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C16 177.9(5) . . ?
C24 N3 C31 108.6(3) . . ?
C24 N3 C32 126.5(3) . . ?
C31 N3 C32 124.6(3) . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C25 119.8(4) . . ?
C25 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(4) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.7 . . ?
C22 C23 C24 118.5(4) . . ?
C24 C23 H23 120.7 . . ?
N3 C24 C23 130.6(3) . . ?
N3 C24 C25 109.4(3) . . ?
C23 C24 C25 119.9(3) . . ?
C20 C25 C24 120.2(4) . . ?
C20 C25 C26 133.9(4) . . ?
C24 C25 C26 105.8(3) . . ?
C27 C26 C25 132.3(3) . . ?
C27 C26 C31 119.8(4) . . ?
C31 C26 C25 107.8(3) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 C26 118.4(4) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 H28 119.3 . . ?
C27 C28 C29 121.4(4) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 121.2 . . ?
C29 C30 C31 117.6(4) . . ?
C31 C30 H30 121.2 . . ?
N3 C31 C26 108.2(3) . . ?
C30 C31 N3 129.9(3) . . ?
C30 C31 C26 121.8(3) . . ?
C33 C32 N3 120.2(3) . . ?
C33 C32 C37 120.1(3) . . ?
C37 C32 N3 119.7(3) . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.3(3) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.3(3) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C38 119.8(3) . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 C38 119.7(4) . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 119.9(3) . . ?
C37 C36 H36 120.0 . . ?
C32 C37 H37 120.1 . . ?
C36 C37 C32 119.8(3) . . ?
C36 C37 H37 120.1 . . ?
N4 C38 C35 178.1(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 C5 1.393(5) . ?
N1 C8 1.405(5) . ?
N1 C13 1.420(4) . ?
N2 C19 1.145(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(6) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.418(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 C6 1.426(5) . ?
C6 C7 1.440(5) . ?
C7 C8 1.412(5) . ?
C7 C12 1.403(5) . ?
C8 C9 1.382(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.400(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(5) . ?
C13 C18 1.394(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(5) . ?
C16 C17 1.400(5) . ?
C16 C19 1.443(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(5) . ?
C18 H18 0.9300 . ?
N3 C24 1.390(5) . ?
N3 C31 1.405(5) . ?
N3 C32 1.424(4) . ?
N4 C38 1.146(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(6) . ?
C20 C25 1.385(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.404(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.404(5) . ?
C24 C25 1.419(5) . ?
C25 C26 1.451(5) . ?
C26 C27 1.406(5) . ?
C26 C31 1.409(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.408(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.389(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.391(5) . ?
C32 C33 1.382(5) . ?
C32 C37 1.396(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.392(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.394(5) . ?
C35 C36 1.382(5) . ?
C35 C38 1.448(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.388(5) . ?
C37 H37 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 C5 C6 C1 -176.6(3) . . . . ?
N1 C5 C6 C7 0.8(4) . . . . ?
N1 C8 C9 C10 176.1(4) . . . . ?
N1 C13 C14 C15 -176.3(3) . . . . ?
N1 C13 C18 C17 178.2(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C6 C7 C8 176.4(4) . . . . ?
C1 C6 C7 C12 -7.4(7) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C6 C7 -176.8(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 N1 175.9(4) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 177.6(3) . . . . ?
C5 N1 C8 C7 0.6(4) . . . . ?
C5 N1 C8 C9 -176.9(4) . . . . ?
C5 N1 C13 C14 -139.5(4) . . . . ?
C5 N1 C13 C18 42.1(5) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C12 175.7(4) . . . . ?
C6 C1 C2 C3 0.2(6) . . . . ?
C6 C7 C8 N1 0.0(4) . . . . ?
C6 C7 C8 C9 177.7(3) . . . . ?
C6 C7 C12 C11 -176.6(4) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 N1 C5 C4 -177.2(4) . . . . ?
C8 N1 C5 C6 -0.9(4) . . . . ?
C8 N1 C13 C14 47.1(5) . . . . ?
C8 N1 C13 C18 -131.3(4) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C10 C11 C12 C7 0.8(6) . . . . ?
C12 C7 C8 N1 -176.9(3) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
C13 N1 C5 C4 8.5(6) . . . . ?
C13 N1 C5 C6 -175.2(3) . . . . ?
C13 N1 C8 C7 174.9(3) . . . . ?
C13 N1 C8 C9 -2.5(6) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
C14 C15 C16 C17 -0.7(6) . . . . ?
C14 C15 C16 C19 179.7(4) . . . . ?
C15 C16 C17 C18 2.5(5) . . . . ?
C15 C16 C19 N2 -145(13) . . . . ?
C16 C17 C18 C13 -2.1(5) . . . . ?
C17 C16 C19 N2 36(14) . . . . ?
C18 C13 C14 C15 2.1(5) . . . . ?
C19 C16 C17 C18 -177.8(4) . . . . ?
N3 C24 C25 C20 177.7(3) . . . . ?
N3 C24 C25 C26 -0.8(4) . . . . ?
N3 C32 C33 C34 177.2(3) . . . . ?
N3 C32 C37 C36 -179.2(3) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C20 C25 C26 C27 6.5(7) . . . . ?
C20 C25 C26 C31 -177.7(4) . . . . ?
C21 C20 C25 C24 0.4(5) . . . . ?
C21 C20 C25 C26 178.3(4) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
C22 C23 C24 N3 -177.2(4) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C24 C25 C20 0.2(5) . . . . ?
C23 C24 C25 C26 -178.2(3) . . . . ?
C24 N3 C31 C26 -0.6(4) . . . . ?
C24 N3 C31 C30 176.6(4) . . . . ?
C24 N3 C32 C33 139.0(4) . . . . ?
C24 N3 C32 C37 -41.1(5) . . . . ?
C24 C25 C26 C27 -175.4(4) . . . . ?
C24 C25 C26 C31 0.4(4) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?
C25 C26 C27 C28 176.6(4) . . . . ?
C25 C26 C31 N3 0.1(4) . . . . ?
C25 C26 C31 C30 -177.4(3) . . . . ?
C26 C27 C28 C29 -1.5(6) . . . . ?
C27 C26 C31 N3 176.5(3) . . . . ?
C27 C26 C31 C30 -1.0(5) . . . . ?
C27 C28 C29 C30 1.5(6) . . . . ?
C28 C29 C30 C31 -1.2(5) . . . . ?
C29 C30 C31 N3 -175.9(3) . . . . ?
C29 C30 C31 C26 1.0(5) . . . . ?
C31 N3 C24 C23 177.9(4) . . . . ?
C31 N3 C24 C25 0.9(4) . . . . ?
C31 N3 C32 C33 -46.8(5) . . . . ?
C31 N3 C32 C37 133.1(4) . . . . ?
C31 C26 C27 C28 1.2(5) . . . . ?
C32 N3 C24 C23 -7.1(6) . . . . ?
C32 N3 C24 C25 175.8(3) . . . . ?
C32 N3 C31 C26 -175.6(3) . . . . ?
C32 N3 C31 C30 1.6(6) . . . . ?
C32 C33 C34 C35 2.5(6) . . . . ?
C33 C32 C37 C36 0.7(5) . . . . ?
C33 C34 C35 C36 -0.3(6) . . . . ?
C33 C34 C35 C38 -179.2(4) . . . . ?
C34 C35 C36 C37 -1.7(6) . . . . ?
C34 C35 C38 N4 128(14) . . . . ?
C35 C36 C37 C32 1.5(6) . . . . ?
C36 C35 C38 N4 -51(14) . . . . ?
C37 C32 C33 C34 -2.7(6) . . . . ?
C38 C35 C36 C37 177.2(4) . . . . ?
