#------------------------------------------------------------------------------
#$Date: 2024-05-30 04:04:56 +0300 (Thu, 30 May 2024) $
#$Revision: 292112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248747.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_7248747
loop_
_publ_author_name
'Chen‡, Meiling'
'Chen‡, Yuzhuo'
'Su, Zhongzhen'
'Li, Yuchun'
'Fei, Hanxiao'
'Zhang, Hua'
'Wu, Yunan'
_publ_section_title
;
 Achievement of efficient thermally activated delayed fluorescence
 materials based on 1,8-naphthalimide derivatives exhibiting piezochromic
 and thermochromic luminescence
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              17434
_journal_page_last               17439
_journal_paper_doi               10.1039/D4RA02981J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C36 H22 N2 O2, C H2 Cl2'
_chemical_formula_sum            'C37 H24 Cl2 N2 O2'
_chemical_formula_weight         599.48
_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   geom
_audit_creation_date             2024-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-31 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.24880(10)
_cell_length_b                   13.19660(10)
_cell_length_c                   16.31220(10)
_cell_measurement_reflns_used    12329
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9470
_cell_measurement_theta_min      4.1460
_cell_volume                     2847.62(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5826
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00 -13.00   1.00    2.00    --  -41.64 -77.00 -60.00   25
  2  ω    -55.00  33.00   1.00    2.00    --  -41.64  37.00  90.00   88
  3  ω     23.00  84.00   1.00    2.00    --   41.64-125.00 150.00   61
  4  ω     61.00 108.00   1.00    4.00    --  107.79 -94.00 120.00   47
  5  ω     40.00 133.00   1.00    4.00    --  107.79 -45.00  60.00   93
  6  ω     84.00 122.00   1.00    4.00    --  107.79-125.00 -60.00   38
  7  ω     37.00 100.00   1.00    4.00    --  107.79 -61.00-150.00   63
  8  ω     83.00 173.00   1.00    4.00    --  107.79  30.00-150.00   90
  9  ω    130.00 174.00   1.00    4.00    --  107.79 125.00 -30.00   44
 10  ω    142.00 171.00   1.00    4.00    --  107.79 125.00  90.00   29
 11  ω    123.00 174.00   1.00    4.00    --  107.79  61.00 150.00   51
 12  ω    121.00 177.00   1.00    4.00    --  107.79 125.00 120.00   56
 13  ω    107.00 132.00   1.00    4.00    --  107.79 125.00   0.00   25
 14  ω     94.00 128.00   1.00    4.00    --  107.79 125.00  90.00   34
 15  ω     91.00 118.00   1.00    4.00    --  107.79  61.00 150.00   27
 16  ω     90.00 176.00   1.00    4.00    --  107.79  45.00   0.00   86
 17  ω     96.00 159.00   1.00    4.00    --  107.79 125.00-150.00   63
 18  ω     29.00  96.00   1.00    2.00    --   41.64-125.00 -60.00   67
 19  ω     39.00 116.00   1.00    4.00    --  107.79-125.00  90.00   77
 20  ω   -118.00 -77.00   1.00    2.00    --  -41.64 -77.00 -60.00   41
 21  ω   -125.00  13.00   1.00    2.00    --  -41.64   0.00  60.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0778908000
_diffrn_orient_matrix_UB_12      0.0584233000
_diffrn_orient_matrix_UB_13      0.0484159000
_diffrn_orient_matrix_UB_21      0.0257071000
_diffrn_orient_matrix_UB_22      0.0980106000
_diffrn_orient_matrix_UB_23      -0.0457023000
_diffrn_orient_matrix_UB_31      -0.0826590000
_diffrn_orient_matrix_UB_32      -0.0246364000
_diffrn_orient_matrix_UB_33      -0.0672043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.156
_diffrn_reflns_theta_min         4.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.857
_refine_diff_density_min         -1.531
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0757
_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)+(0.1357P)²+5.2086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5331
_reflns_number_total             5703
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02981j2.cif
_cod_data_source_block           17110904
_cod_database_code               7248747
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     mp
_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   0.719
_shelx_estimated_absorpt_t_min   0.452
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H37a(0.75) H37b(0.75) H37c(0.25) H37d(0.25) Cl2(0.75) Cl3(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C37(H37a,H37b), C37(H37c,H37d)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C26(H26), C34(H34), C9(H9), C19(H19), C5(H5), C21(H21),
 C11(H11), C23(H23), C3(H3), C25(H25), C13(H13), C27(H27), C7(H7), C29(H29),
 C15(H15), C31(H31), C2(H2), C33(H33), C17(H17), C35(H35)
;
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.666
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
O1 O 0.45241(15) 0.78883(16) 0.36625(11) 0.0268(4) Uani 1 1 d . . . . .
O2 O 0.23109(14) 0.80239(18) 0.56839(12) 0.0313(5) Uani 1 1 d . . . . .
N1 N 0.34421(16) 0.79014(16) 0.46918(13) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.73946(16) 0.87110(18) 0.97976(13) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.57245(18) 0.91754(18) 0.63048(15) 0.0178(5) Uani 1 1 d . . . . .
C4 C 0.39827(18) 0.85717(19) 0.60434(15) 0.0185(5) Uani 1 1 d . . . . .
C6 C 0.43765(19) 0.81179(19) 0.43664(15) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.49465(18) 0.87913(18) 0.57531(15) 0.0170(5) Uani 1 1 d . . . . .
C10 C 0.51440(18) 0.86077(18) 0.49249(15) 0.0180(5) Uani 1 1 d . . . . .
C12 C 0.66875(18) 0.86354(19) 1.03945(15) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.65161(18) 0.90095(19) 0.84674(15) 0.0196(5) Uani 1 1 d . . . . .
H14 H 0.615596 0.841182 0.852831 0.024 Uiso 1 1 calc R U . . .
C16 C 0.26945(19) 0.7384(2) 0.41635(14) 0.0194(5) Uani 1 1 d . . . . .
C18 C 0.66823(19) 0.9369(2) 0.59872(16) 0.0217(5) Uani 1 1 d . . . . .
H18 H 0.720990 0.960017 0.633807 0.026 Uiso 1 1 calc R U . . .
C20 C 0.63244(19) 0.9613(2) 0.77735(15) 0.0198(5) Uani 1 1 d . . . . .
C22 C 0.71580(19) 0.82310(19) 1.11205(15) 0.0199(5) Uani 1 1 d . . . . .
C24 C 0.31731(19) 0.8158(2) 0.54849(15) 0.0209(5) Uani 1 1 d . . . . .
C26 C 0.56697(19) 0.89160(19) 1.03497(16) 0.0208(5) Uani 1 1 d . . . . .
H26 H 0.536175 0.917347 0.986758 0.025 Uiso 1 1 calc R U . . .
C28 C 0.72459(19) 0.9301(2) 0.90685(15) 0.0207(5) Uani 1 1 d . . . . .
C30 C 0.55207(19) 0.92941(19) 0.71521(15) 0.0197(5) Uani 1 1 d . . . . .
C32 C 0.8205(2) 0.8054(2) 1.09494(16) 0.0219(5) Uani 1 1 d . . . . .
C34 C 0.38013(19) 0.8715(2) 0.68600(16) 0.0225(5) Uani 1 1 d . . . . .
H34 H 0.316459 0.857918 0.704666 0.027 Uiso 1 1 calc R U . . .
C36 C 0.83248(19) 0.8375(2) 1.01374(16) 0.0229(5) Uani 1 1 d . . . . .
C9 C 0.6869(2) 1.0510(2) 0.76932(16) 0.0228(5) Uani 1 1 d . . . . .
H9 H 0.673786 1.092435 0.723843 0.027 Uiso 1 1 calc R U . . .
C19 C 0.6596(2) 0.8119(2) 1.18125(16) 0.0233(5) Uani 1 1 d . . . . .
H19 H 0.689496 0.785107 1.229421 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4573(2) 0.9063(2) 0.74067(15) 0.0226(5) Uani 1 1 d . . . . .
H5 H 0.444335 0.914140 0.795772 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6074(2) 0.8834(2) 0.46318(16) 0.0225(5) Uani 1 1 d . . . . .
H21 H 0.619127 0.873132 0.408108 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1948(2) 0.7935(2) 0.37481(16) 0.0230(5) Uani 1 1 d . . . . .
H11 H 0.192411 0.863571 0.380396 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5137(2) 0.8797(2) 1.10480(17) 0.0237(5) Uani 1 1 d . . . . .
H23 H 0.445790 0.897946 1.103207 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6844(2) 0.9221(2) 0.51710(17) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.747011 0.937779 0.497325 0.030 Uiso 1 1 calc R U . . .
C25 C 0.7803(2) 1.0185(2) 0.89755(16) 0.0254(6) Uani 1 1 d . . . . .
H25 H 0.830216 1.036959 0.937047 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2738(2) 0.6340(2) 0.40910(17) 0.0260(6) Uani 1 1 d . . . . .
H13 H 0.324500 0.597450 0.437566 0.031 Uiso 1 1 calc R U . . .
C27 C 0.5588(2) 0.8411(2) 1.17777(17) 0.0253(6) Uani 1 1 d . . . . .
H27 H 0.521223 0.835028 1.224015 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7606(2) 1.0786(2) 0.82890(17) 0.0258(6) Uani 1 1 d . . . . .
H7 H 0.797131 1.138047 0.822697 0.031 Uiso 1 1 calc R U . . .
C29 C 0.1225(2) 0.7432(2) 0.32417(17) 0.0276(6) Uani 1 1 d . . . . .
H29 H 0.071905 0.779802 0.295679 0.033 Uiso 1 1 calc R U . . .
C15 C 0.9037(2) 0.7659(2) 1.14074(17) 0.0268(6) Uani 1 1 d . . . . .
H15 H 0.897119 0.743651 1.194276 0.032 Uiso 1 1 calc R U . . .
C31 C 0.1264(2) 0.6389(2) 0.31643(17) 0.0307(6) Uani 1 1 d . . . . .
H31 H 0.078360 0.605383 0.282668 0.037 Uiso 1 1 calc R U . . .
C2 C 0.9253(2) 0.8325(2) 0.97777(17) 0.0296(6) Uani 1 1 d . . . . .
H2 H 0.932315 0.854382 0.924189 0.035 Uiso 1 1 calc R U . . .
C33 C 0.9961(2) 0.7604(2) 1.10513(18) 0.0310(6) Uani 1 1 d . . . . .
H33 H 1.051919 0.734153 1.135091 0.037 Uiso 1 1 calc R U . . .
C17 C 1.0065(2) 0.7939(3) 1.02468(19) 0.0316(6) Uani 1 1 d . . . . .
H17 H 1.069445 0.790088 1.002240 0.038 Uiso 1 1 calc R U . . .
C35 C 0.2017(2) 0.5844(2) 0.35895(19) 0.0315(6) Uani 1 1 d . . . . .
H35 H 0.203932 0.514244 0.353847 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.83835(12) 0.58518(14) 0.83098(9) 0.0879(5) Uani 1 1 d . . . . .
C37 C 0.9350(5) 0.5325(5) 0.8960(3) 0.090(2) Uani 1 1 d . . . . .
H37A H 0.953996 0.582596 0.937509 0.108 Uiso 0.75 1 calc R U P A 1
H37B H 0.906495 0.475283 0.924090 0.108 Uiso 0.75 1 calc R U P A 1
H37C H 0.946927 0.466863 0.871528 0.108 Uiso 0.25 1 calc R U P B 2
H37D H 0.993769 0.572966 0.884920 0.108 Uiso 0.25 1 calc R U P B 2
Cl2 Cl 1.03422(11) 0.49526(12) 0.85726(14) 0.0782(6) Uani 0.75 1 d . . P C 1
Cl3 Cl 0.9463(7) 0.5142(8) 0.9781(6) 0.131(3) Uani 0.25 1 d . . P C 2
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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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
C6 N1 C16 117.4(2) . . ?
C24 N1 C6 125.1(2) . . ?
C24 N1 C16 117.6(2) . . ?
C12 N2 C28 123.7(2) . . ?
C12 N2 C36 108.3(2) . . ?
C36 N2 C28 125.7(2) . . ?
C8 C1 C30 118.7(2) . . ?
C18 C1 C8 117.6(2) . . ?
C18 C1 C30 123.6(2) . . ?
C8 C4 C24 120.5(2) . . ?
C34 C4 C8 120.2(2) . . ?
C34 C4 C24 119.2(2) . . ?
O1 C6 N1 119.9(2) . . ?
O1 C6 C10 123.5(2) . . ?
N1 C6 C10 116.6(2) . . ?
C4 C8 C1 119.7(2) . . ?
C10 C8 C1 120.0(2) . . ?
C10 C8 C4 120.2(2) . . ?
C8 C10 C6 120.5(2) . . ?
C21 C10 C6 118.6(2) . . ?
C21 C10 C8 120.8(2) . . ?
N2 C12 C22 109.3(2) . . ?
N2 C12 C26 129.0(2) . . ?
C26 C12 C22 121.6(2) . . ?
C20 C14 H14 119.9 . . ?
C28 C14 H14 119.9 . . ?
C28 C14 C20 120.1(2) . . ?
C11 C16 N1 119.6(2) . . ?
C11 C16 C13 121.1(2) . . ?
C13 C16 N1 119.3(2) . . ?
C1 C18 H18 119.4 . . ?
C3 C18 C1 121.2(2) . . ?
C3 C18 H18 119.4 . . ?
C14 C20 C30 118.8(2) . . ?
C14 C20 C9 119.2(2) . . ?
C9 C20 C30 122.0(2) . . ?
C12 C22 C32 106.4(2) . . ?
C19 C22 C12 119.2(2) . . ?
C19 C22 C32 134.3(2) . . ?
O2 C24 N1 120.1(2) . . ?
O2 C24 C4 123.4(2) . . ?
N1 C24 C4 116.5(2) . . ?
C12 C26 H26 121.2 . . ?
C23 C26 C12 117.6(2) . . ?
C23 C26 H26 121.2 . . ?
C14 C28 N2 119.7(2) . . ?
C14 C28 C25 120.4(2) . . ?
C25 C28 N2 119.9(2) . . ?
C1 C30 C20 121.5(2) . . ?
C5 C30 C1 119.4(2) . . ?
C5 C30 C20 119.1(2) . . ?
C36 C32 C22 107.0(2) . . ?
C15 C32 C22 133.8(2) . . ?
C15 C32 C36 119.2(2) . . ?
C4 C34 H34 120.0 . . ?
C4 C34 C5 120.1(2) . . ?
C5 C34 H34 120.0 . . ?
N2 C36 C32 109.0(2) . . ?
C2 C36 N2 128.9(2) . . ?
C2 C36 C32 122.1(2) . . ?
C20 C9 H9 119.9 . . ?
C7 C9 C20 120.3(2) . . ?
C7 C9 H9 119.9 . . ?
C22 C19 H19 120.2 . . ?
C27 C19 C22 119.6(2) . . ?
C27 C19 H19 120.2 . . ?
C30 C5 C34 121.8(2) . . ?
C30 C5 H5 119.1 . . ?
C34 C5 H5 119.1 . . ?
C10 C21 H21 120.2 . . ?
C10 C21 C3 119.6(2) . . ?
C3 C21 H21 120.2 . . ?
C16 C11 H11 120.3 . . ?
C16 C11 C29 119.4(2) . . ?
C29 C11 H11 120.3 . . ?
C26 C23 H23 119.0 . . ?
C26 C23 C27 122.0(2) . . ?
C27 C23 H23 119.0 . . ?
C18 C3 C21 120.8(2) . . ?
C18 C3 H3 119.6 . . ?
C21 C3 H3 119.6 . . ?
C28 C25 H25 120.3 . . ?
C7 C25 C28 119.4(2) . . ?
C7 C25 H25 120.3 . . ?
C16 C13 H13 120.3 . . ?
C16 C13 C35 119.3(3) . . ?
C35 C13 H13 120.3 . . ?
C19 C27 C23 120.1(2) . . ?
C19 C27 H27 120.0 . . ?
C23 C27 H27 120.0 . . ?
C9 C7 H7 119.7 . . ?
C25 C7 C9 120.6(2) . . ?
C25 C7 H7 119.7 . . ?
C11 C29 H29 120.0 . . ?
C31 C29 C11 120.0(3) . . ?
C31 C29 H29 120.0 . . ?
C32 C15 H15 120.5 . . ?
C33 C15 C32 119.0(3) . . ?
C33 C15 H15 120.5 . . ?
C29 C31 H31 120.0 . . ?
C29 C31 C35 120.0(3) . . ?
C35 C31 H31 120.0 . . ?
C36 C2 H2 121.2 . . ?
C17 C2 C36 117.5(3) . . ?
C17 C2 H2 121.2 . . ?
C15 C33 H33 119.6 . . ?
C15 C33 C17 120.8(3) . . ?
C17 C33 H33 119.6 . . ?
C2 C17 C33 121.4(3) . . ?
C2 C17 H17 119.3 . . ?
C33 C17 H17 119.3 . . ?
C13 C35 H35 119.9 . . ?
C31 C35 C13 120.3(3) . . ?
C31 C35 H35 119.9 . . ?
Cl1 C37 H37A 107.7 . . ?
Cl1 C37 H37B 107.7 . . ?
Cl1 C37 H37C 103.6 . . ?
Cl1 C37 H37D 103.6 . . ?
H37A C37 H37B 107.1 . . ?
H37C C37 H37D 105.3 . . ?
Cl2 C37 Cl1 118.6(4) . . ?
Cl2 C37 H37A 107.7 . . ?
Cl2 C37 H37B 107.7 . . ?
Cl3 C37 Cl1 134.4(7) . . ?
Cl3 C37 H37C 103.6 . . ?
Cl3 C37 H37D 103.6 . . ?
C37 Cl3 Cl3 121.9(10) . 3_767 ?
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
O1 C6 1.214(3) . ?
O2 C24 1.218(3) . ?
N1 C6 1.403(3) . ?
N1 C16 1.448(3) . ?
N1 C24 1.402(3) . ?
N2 C12 1.392(3) . ?
N2 C28 1.426(3) . ?
N2 C36 1.396(3) . ?
C1 C8 1.424(3) . ?
C1 C18 1.420(4) . ?
C1 C30 1.431(3) . ?
C4 C8 1.416(3) . ?
C4 C24 1.473(3) . ?
C4 C34 1.380(3) . ?
C6 C10 1.476(3) . ?
C8 C10 1.411(3) . ?
C10 C21 1.379(4) . ?
C12 C22 1.412(3) . ?
C12 C26 1.396(4) . ?
C14 H14 0.9300 . ?
C14 C20 1.396(4) . ?
C14 C28 1.392(3) . ?
C16 C11 1.375(4) . ?
C16 C13 1.385(4) . ?
C18 H18 0.9300 . ?
C18 C3 1.374(4) . ?
C20 C30 1.489(3) . ?
C20 C9 1.397(4) . ?
C22 C32 1.449(4) . ?
C22 C19 1.394(4) . ?
C26 H26 0.9300 . ?
C26 C23 1.382(4) . ?
C28 C25 1.393(4) . ?
C30 C5 1.379(4) . ?
C32 C36 1.408(4) . ?
C32 C15 1.398(4) . ?
C34 H34 0.9300 . ?
C34 C5 1.396(4) . ?
C36 C2 1.393(4) . ?
C9 H9 0.9300 . ?
C9 C7 1.387(4) . ?
C19 H19 0.9300 . ?
C19 C27 1.389(4) . ?
C5 H5 0.9300 . ?
C21 H21 0.9300 . ?
C21 C3 1.405(4) . ?
C11 H11 0.9300 . ?
C11 C29 1.397(4) . ?
C23 H23 0.9300 . ?
C23 C27 1.398(4) . ?
C3 H3 0.9300 . ?
C25 H25 0.9300 . ?
C25 C7 1.385(4) . ?
C13 H13 0.9300 . ?
C13 C35 1.387(4) . ?
C27 H27 0.9300 . ?
C7 H7 0.9300 . ?
C29 H29 0.9300 . ?
C29 C31 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C33 1.387(4) . ?
C31 H31 0.9300 . ?
C31 C35 1.385(4) . ?
C2 H2 0.9300 . ?
C2 C17 1.383(4) . ?
C33 H33 0.9300 . ?
C33 C17 1.399(4) . ?
C17 H17 0.9300 . ?
C35 H35 0.9300 . ?
Cl1 C37 1.760(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 H37C 0.9700 . ?
C37 H37D 0.9700 . ?
C37 Cl2 1.569(7) . ?
C37 Cl3 1.361(11) . ?
Cl3 Cl3 1.600(19) 3_767 ?
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 C6 C10 C8 -175.6(2) . . . . ?
O1 C6 C10 C21 1.1(4) . . . . ?
N1 C6 C10 C8 3.2(3) . . . . ?
N1 C6 C10 C21 179.9(2) . . . . ?
N1 C16 C11 C29 -179.7(2) . . . . ?
N1 C16 C13 C35 179.5(2) . . . . ?
N2 C12 C22 C32 0.0(3) . . . . ?
N2 C12 C22 C19 177.9(2) . . . . ?
N2 C12 C26 C23 -177.5(3) . . . . ?
N2 C28 C25 C7 -175.9(2) . . . . ?
N2 C36 C2 C17 -178.7(3) . . . . ?
C1 C8 C10 C6 174.1(2) . . . . ?
C1 C8 C10 C21 -2.6(4) . . . . ?
C1 C18 C3 C21 -2.5(4) . . . . ?
C1 C30 C5 C34 0.0(4) . . . . ?
C4 C8 C10 C6 -4.4(4) . . . . ?
C4 C8 C10 C21 178.9(2) . . . . ?
C4 C34 C5 C30 1.4(4) . . . . ?
C6 N1 C16 C11 -97.8(3) . . . . ?
C6 N1 C16 C13 82.8(3) . . . . ?
C6 N1 C24 O2 173.0(2) . . . . ?
C6 N1 C24 C4 -7.9(4) . . . . ?
C6 C10 C21 C3 -174.6(2) . . . . ?
C8 C1 C18 C3 2.0(4) . . . . ?
C8 C1 C30 C20 175.0(2) . . . . ?
C8 C1 C30 C5 -1.9(4) . . . . ?
C8 C4 C24 O2 -174.5(3) . . . . ?
C8 C4 C24 N1 6.4(4) . . . . ?
C8 C4 C34 C5 -0.9(4) . . . . ?
C8 C10 C21 C3 2.1(4) . . . . ?
C10 C21 C3 C18 0.4(4) . . . . ?
C12 N2 C28 C14 -68.1(3) . . . . ?
C12 N2 C28 C25 109.5(3) . . . . ?
C12 N2 C36 C32 1.7(3) . . . . ?
C12 N2 C36 C2 -179.0(3) . . . . ?
C12 C22 C32 C36 1.1(3) . . . . ?
C12 C22 C32 C15 -179.0(3) . . . . ?
C12 C22 C19 C27 -0.3(4) . . . . ?
C12 C26 C23 C27 0.0(4) . . . . ?
C14 C20 C30 C1 -125.5(3) . . . . ?
C14 C20 C30 C5 51.5(3) . . . . ?
C14 C20 C9 C7 1.3(4) . . . . ?
C14 C28 C25 C7 1.7(4) . . . . ?
C16 N1 C6 O1 1.3(4) . . . . ?
C16 N1 C6 C10 -177.6(2) . . . . ?
C16 N1 C24 O2 -6.3(4) . . . . ?
C16 N1 C24 C4 172.9(2) . . . . ?
C16 C11 C29 C31 0.2(4) . . . . ?
C16 C13 C35 C31 0.2(4) . . . . ?
C18 C1 C8 C4 179.0(2) . . . . ?
C18 C1 C8 C10 0.6(3) . . . . ?
C18 C1 C30 C20 -1.4(4) . . . . ?
C18 C1 C30 C5 -178.4(2) . . . . ?
C20 C14 C28 N2 176.3(2) . . . . ?
C20 C14 C28 C25 -1.2(4) . . . . ?
C20 C30 C5 C34 -177.0(2) . . . . ?
C20 C9 C7 C25 -0.8(4) . . . . ?
C22 C12 C26 C23 0.9(4) . . . . ?
C22 C32 C36 N2 -1.7(3) . . . . ?
C22 C32 C36 C2 179.0(3) . . . . ?
C22 C32 C15 C33 -179.2(3) . . . . ?
C22 C19 C27 C23 1.2(4) . . . . ?
C24 N1 C6 O1 -177.9(2) . . . . ?
C24 N1 C6 C10 3.2(4) . . . . ?
C24 N1 C16 C11 81.5(3) . . . . ?
C24 N1 C16 C13 -97.9(3) . . . . ?
C24 C4 C8 C1 -179.0(2) . . . . ?
C24 C4 C8 C10 -0.5(4) . . . . ?
C24 C4 C34 C5 177.1(2) . . . . ?
C26 C12 C22 C32 -178.7(2) . . . . ?
C26 C12 C22 C19 -0.7(4) . . . . ?
C26 C23 C27 C19 -1.0(4) . . . . ?
C28 N2 C12 C22 -164.5(2) . . . . ?
C28 N2 C12 C26 14.0(4) . . . . ?
C28 N2 C36 C32 164.8(2) . . . . ?
C28 N2 C36 C2 -16.0(5) . . . . ?
C28 C14 C20 C30 -178.4(2) . . . . ?
C28 C14 C20 C9 -0.2(4) . . . . ?
C28 C25 C7 C9 -0.6(4) . . . . ?
C30 C1 C8 C4 2.4(3) . . . . ?
C30 C1 C8 C10 -176.1(2) . . . . ?
C30 C1 C18 C3 178.5(2) . . . . ?
C30 C20 C9 C7 179.4(2) . . . . ?
C32 C22 C19 C27 176.9(3) . . . . ?
C32 C36 C2 C17 0.4(4) . . . . ?
C32 C15 C33 C17 0.1(5) . . . . ?
C34 C4 C8 C1 -1.0(4) . . . . ?
C34 C4 C8 C10 177.5(2) . . . . ?
C34 C4 C24 O2 7.5(4) . . . . ?
C34 C4 C24 N1 -171.6(2) . . . . ?
C36 N2 C12 C22 -1.0(3) . . . . ?
C36 N2 C12 C26 177.4(3) . . . . ?
C36 N2 C28 C14 131.4(3) . . . . ?
C36 N2 C28 C25 -51.1(4) . . . . ?
C36 C32 C15 C33 0.7(4) . . . . ?
C36 C2 C17 C33 0.4(5) . . . . ?
C9 C20 C30 C1 56.4(3) . . . . ?
C9 C20 C30 C5 -126.7(3) . . . . ?
C19 C22 C32 C36 -176.4(3) . . . . ?
C19 C22 C32 C15 3.5(5) . . . . ?
C11 C16 C13 C35 0.2(4) . . . . ?
C11 C29 C31 C35 0.1(4) . . . . ?
C13 C16 C11 C29 -0.4(4) . . . . ?
C29 C31 C35 C13 -0.3(5) . . . . ?
C15 C32 C36 N2 178.4(2) . . . . ?
C15 C32 C36 C2 -0.9(4) . . . . ?
C15 C33 C17 C2 -0.6(5) . . . . ?
Cl1 C37 Cl3 Cl3 -166.9(9) . . . 3_767 ?
