#------------------------------------------------------------------------------
#$Date: 2022-03-10 03:37:59 +0200 (Thu, 10 Mar 2022) $
#$Revision: 273581 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158566.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_7158566
loop_
_publ_author_name
'Tonkoglazova, Daria'
'Oryabinskaya, Lyubov M.'
'Shcherbatykh, Aleksandr'
'Gulevskaya, Anna V.'
_publ_section_title
;
 Synthesis and crystal structure of pH-sensitive fluorescent pyrene-based
 double aza- and diaza[4]helicenes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00204C
_journal_year                    2022
_chemical_formula_moiety         'C38 H23 N, C D Cl3 '
_chemical_formula_sum            'C39 H23 Cl3 D N'
_chemical_formula_weight         613.95
_chemical_melting_point          519.0(10)
_chemical_name_systematic        5-(p-Tolyl)naphtho[2,1-f]pyreno[2,1-h]quinoline
_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     dual
_audit_creation_date             2021-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-28 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                100.434(2)
_cell_angle_beta                 109.813(2)
_cell_angle_gamma                94.308(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9654(2)
_cell_length_b                   10.8736(2)
_cell_length_c                   14.6459(3)
_cell_measurement_reflns_used    14001
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7750
_cell_measurement_theta_min      3.2910
_cell_volume                     1452.32(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -34.00   0.50    0.45    --  -47.44 115.00 119.00  110
  2  ω   -117.00 -77.00   0.50    0.45    --  -47.44-167.00-115.00   80
  3  ω   -110.00 -85.00   0.50    0.45    --  -47.44 167.00 -94.00   50
  4  ω     49.00 119.00   0.50    0.45    --   47.44 167.00 -94.00  140
  5  ω     12.00  38.00   0.50    0.45    --   47.44-115.00  30.00   52
  6  ω     54.00  79.00   0.50    0.45    --   47.44-167.00-115.00   50
  7  ω   -137.00 -54.00   0.50    1.80    -- -106.00 167.00 -94.00  166
  8  ω   -108.00 -40.00   0.50    1.80    -- -106.00 115.00 119.00  136
  9  ω   -153.00-128.00   0.50    1.80    -- -106.00-115.00  30.00   50
 10  ω   -123.00 -98.00   0.50    1.80    -- -106.00-167.00-115.00   50
 11  ω     86.00 121.00   0.50    1.80    --  113.25-167.00-115.00   70
 12  ω     65.00 101.00   0.50    1.80    --  113.25 167.00 -94.00   72
 13  ω     51.00 109.00   0.50    1.80    --  113.25-115.00  30.00  116
 14  ω    105.00 130.00   0.50    1.80    --  113.25 115.00 119.00   50
 15  ω   -113.00 -75.00   0.50    0.45    --  -47.44-125.00  60.00   76
 16  ω    -24.00  24.00   0.50    0.45    --  -47.44  19.00-150.00   96
 17  ω   -114.00 -25.00   0.50    0.45    --  -47.44 -77.00  60.00  178
 18  ω     78.00 119.00   0.50    0.45    --   47.44 125.00  60.00   82
 19  ω    -17.00  20.00   0.50    0.45    --   47.44 -19.00-180.00   74
 20  ω     74.00 119.00   0.50    0.45    --   47.44 125.00  30.00   90
 21  ω   -177.00-119.00   0.50    1.80    -- -106.00 -15.00  60.00  116
 22  ω    -96.00 -70.00   0.50    1.80    -- -106.00  77.00 -30.00   52
 23  ω   -177.00 -93.00   0.50    1.80    -- -106.00 -45.00  30.00  168
 24  ω   -107.00 -82.00   0.50    1.80    -- -106.00 111.00  55.10   50
 25  ω    -68.00 -42.00   0.50    1.80    -- -106.00  77.00 -30.00   52
 26  ω   -112.00 -39.00   0.50    1.80    -- -106.00 125.00-150.00  146
 27  ω    -64.00 -39.00   0.50    1.80    -- -106.00  61.00 -60.00   50
 28  ω   -166.00-126.00   0.50    1.80    -- -106.00 -15.00  90.00   80
 29  ω   -112.00 -80.00   0.50    1.80    -- -106.00 125.00-180.00   64
 30  ω   -112.00 -35.00   0.50    1.80    -- -106.00 125.00 120.00  154
 31  ω   -175.00-150.00   0.50    1.80    -- -106.00-125.00   0.00   50
 32  ω    -68.00 -34.00   0.50    1.80    -- -106.00  61.00 150.00   68
 33  ω   -121.00 -96.00   0.50    1.80    -- -106.00 138.00 155.21   50
 34  ω    -78.00 -34.00   0.50    1.80    -- -106.00 138.00 155.21   88
 35  ω    -69.00 -33.00   0.50    1.80    -- -106.00  61.00-120.00   72
 36  ω    -69.00 -44.00   0.50    1.80    -- -106.00 111.00  55.10   50
 37  ω   -112.00 -85.00   0.50    1.80    -- -106.00 125.00 -90.00   54
 38  ω   -113.00 -75.00   0.50    1.80    -- -106.00-125.00   0.00   76
 39  ω    101.00 176.00   0.50    1.80    --  113.25  61.00 120.00  150
 40  ω     62.00  88.00   0.50    1.80    --  113.25 -77.00   0.00   52
 41  ω     58.00 106.00   0.50    1.80    --  113.25 -94.00  60.00   96
 42  ω     42.00 108.00   0.50    1.80    --  113.25-125.00 -30.00  132
 43  ω     43.00  69.00   0.50    1.80    --  113.25 -61.00  60.00   52
 44  ω     71.00 101.00   0.50    1.80    --  113.25-125.00   0.00   60
 45  ω     42.00  69.00   0.50    1.80    --  113.25 -61.00  30.00   54
 46  ω    133.00 170.00   0.50    1.80    --  113.25  77.00  90.00   74
 47  ω     44.00 111.00   0.50    1.80    --  113.25-125.00  60.00  134
 48  ω     91.00 130.00   0.50    1.80    --  113.25  77.00  90.00   78
 49  ω     71.00  96.00   0.50    1.80    --  113.25 -94.00-120.00   50
 50  ω    105.00 169.00   0.50    1.80    --  113.25  15.00 -90.00  128
 51  ω     45.00  77.00   0.50    1.80    --  113.25 -94.00-150.00   64
 52  ω    106.00 172.00   0.50    1.80    --  113.25  30.00-150.00  132
 53  ω     44.00  69.00   0.50    1.80    --  113.25 -61.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0690745000
_diffrn_orient_matrix_UB_12      0.1146180000
_diffrn_orient_matrix_UB_13      0.0313147000
_diffrn_orient_matrix_UB_21      0.1005519000
_diffrn_orient_matrix_UB_22      0.0148119000
_diffrn_orient_matrix_UB_23      0.1089052000
_diffrn_orient_matrix_UB_31      0.1127795000
_diffrn_orient_matrix_UB_32      0.0886491000
_diffrn_orient_matrix_UB_33      -0.0172187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20770
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.991
_diffrn_reflns_theta_min         3.288
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0351
_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)+(0.0512P)²+0.5541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4949
_reflns_number_total             5497
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00204c2.cif
_cod_data_source_block           19381_sp-66
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '518-520' was changed to
'519.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1452.32(5)
_cod_original_formula_sum        'C39 H23 D Cl3 N'
_cod_database_code               7158566
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H23 D Cl3 N'
_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   0.886
_shelx_estimated_absorpt_t_min   0.690
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C39(D39)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
  C33(H33), C34(H34), C36(H36), C37(H37)
2.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C)
;
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.712
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.64699(14) 0.61810(12) 0.73123(9) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.57195(17) 0.71306(14) 0.71551(12) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.542261 0.753442 0.767115 0.024 Uiso 1 1 calc R . . . .
C2 C 0.53430(16) 0.75684(14) 0.62801(12) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.480235 0.825033 0.619982 0.023 Uiso 1 1 calc R . . . .
C3 C 0.57762(15) 0.69851(13) 0.55326(11) 0.0175(3) Uani 1 1 d . . . . .
H3 H 0.553858 0.726780 0.492783 0.021 Uiso 1 1 calc R . . . .
C4 C 0.65697(15) 0.59718(13) 0.56618(11) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.70752(15) 0.53463(13) 0.48981(11) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.68744(15) 0.58014(13) 0.40194(11) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.635926 0.649608 0.392064 0.020 Uiso 1 1 calc R . . . .
C7 C 0.73950(15) 0.52775(13) 0.33080(11) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.82383(15) 0.42703(13) 0.34731(11) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.88467(16) 0.37310(14) 0.27790(11) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.862421 0.398981 0.216512 0.023 Uiso 1 1 calc R . . . .
C10 C 0.97508(17) 0.28426(14) 0.29720(11) 0.0199(3) Uani 1 1 d . . . . .
H10 H 1.012108 0.246781 0.248681 0.024 Uiso 1 1 calc R . . . .
C11 C 1.01234(16) 0.24928(13) 0.38922(12) 0.0187(3) Uani 1 1 d . . . . .
H11 H 1.080244 0.192380 0.404925 0.022 Uiso 1 1 calc R . . . .
C12 C 0.95143(15) 0.29666(13) 0.45665(11) 0.0171(3) Uani 1 1 d . . . . .
H12 H 0.978457 0.272009 0.518670 0.020 Uiso 1 1 calc R . . . .
C13 C 0.84895(15) 0.38162(13) 0.43641(11) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.77887(15) 0.43012(13) 0.50453(11) 0.0156(3) Uani 1 1 d . . . . .
C15 C 0.77843(15) 0.37289(13) 0.58753(11) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.75672(15) 0.44523(13) 0.67119(11) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.68973(15) 0.55933(13) 0.65801(11) 0.0160(3) Uani 1 1 d . . . . .
C18 C 0.78616(15) 0.39565(14) 0.75946(11) 0.0160(3) Uani 1 1 d . . . . .
C19 C 0.80735(16) 0.47108(14) 0.85612(11) 0.0189(3) Uani 1 1 d . . . . .
H19 H 0.805673 0.559527 0.863706 0.023 Uiso 1 1 calc R . . . .
C20 C 0.82963(16) 0.41931(15) 0.93660(11) 0.0210(3) Uani 1 1 d . . . . .
H20 H 0.845065 0.472722 0.999330 0.025 Uiso 1 1 calc R . . . .
C21 C 0.83054(16) 0.28643(15) 0.92970(11) 0.0210(3) Uani 1 1 d . . . . .
C22 C 0.84328(19) 0.22916(17) 1.01013(13) 0.0285(4) Uani 1 1 d . . . . .
H22 H 0.851844 0.279687 1.072527 0.034 Uiso 1 1 calc R . . . .
C23 C 0.8436(2) 0.10004(18) 0.99991(13) 0.0315(4) Uani 1 1 d . . . . .
H23 H 0.851049 0.062721 1.054961 0.038 Uiso 1 1 calc R . . . .
C24 C 0.83291(19) 0.02475(16) 0.90952(13) 0.0265(3) Uani 1 1 d . . . . .
H24 H 0.833388 -0.063687 0.903369 0.032 Uiso 1 1 calc R . . . .
C25 C 0.82155(16) 0.07772(15) 0.82781(12) 0.0204(3) Uani 1 1 d . . . . .
C26 C 0.81159(16) 0.00216(14) 0.73370(12) 0.0202(3) Uani 1 1 d . . . . .
H26 H 0.814582 -0.086037 0.727009 0.024 Uiso 1 1 calc R . . . .
C27 C 0.79802(16) 0.05453(14) 0.65453(11) 0.0185(3) Uani 1 1 d . . . . .
H27 H 0.791323 0.002357 0.593184 0.022 Uiso 1 1 calc R . . . .
C28 C 0.79355(15) 0.18789(13) 0.66155(11) 0.0161(3) Uani 1 1 d . . . . .
C29 C 0.78819(15) 0.24358(14) 0.58309(11) 0.0164(3) Uani 1 1 d . . . . .
H29 H 0.791190 0.192818 0.523958 0.020 Uiso 1 1 calc R . . . .
C30 C 0.80074(14) 0.26583(14) 0.75333(11) 0.0160(3) Uani 1 1 d . . . . .
C31 C 0.81794(15) 0.21010(14) 0.83679(11) 0.0179(3) Uani 1 1 d . . . . .
C32 C 0.71209(16) 0.58041(13) 0.24015(11) 0.0169(3) Uani 1 1 d . . . . .
C33 C 0.57139(16) 0.58195(14) 0.17795(11) 0.0189(3) Uani 1 1 d . . . . .
H33 H 0.492804 0.546329 0.192269 0.023 Uiso 1 1 calc R . . . .
C34 C 0.54463(17) 0.63503(14) 0.09513(11) 0.0212(3) Uani 1 1 d . . . . .
H34 H 0.447805 0.634192 0.053276 0.025 Uiso 1 1 calc R . . . .
C35 C 0.65687(18) 0.68938(14) 0.07229(11) 0.0210(3) Uani 1 1 d . . . . .
C36 C 0.79788(17) 0.68863(14) 0.13486(12) 0.0212(3) Uani 1 1 d . . . . .
H36 H 0.876179 0.725455 0.120859 0.025 Uiso 1 1 calc R . . . .
C37 C 0.82566(16) 0.63483(14) 0.21738(11) 0.0191(3) Uani 1 1 d . . . . .
H37 H 0.922539 0.634923 0.258787 0.023 Uiso 1 1 calc R . . . .
C38 C 0.6266(2) 0.74664(17) -0.01771(13) 0.0300(4) Uani 1 1 d . . . . .
H38A H 0.642683 0.688187 -0.071074 0.045 Uiso 1 1 calc GR . . . .
H38B H 0.691300 0.826624 -0.000237 0.045 Uiso 1 1 calc GR . . . .
H38C H 0.526302 0.762349 -0.040333 0.045 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.14231(4) 0.06960(4) 0.60477(3) 0.02909(12) Uani 1 1 d . . . . .
Cl2 Cl 0.45095(4) 0.09777(4) 0.65334(4) 0.03268(12) Uani 1 1 d . . . . .
Cl3 Cl 0.32248(5) -0.03251(4) 0.76580(4) 0.03760(13) Uani 1 1 d . . . . .
C39 C 0.31142(17) 0.09077(15) 0.70182(12) 0.0227(3) Uani 1 1 d . . . . .
D39 D 0.322781 0.172564 0.749656 0.027 Uiso 1 1 calc R . . . .
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'
D D 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
C1 N1 C17 118.68(13) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.86(13) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.08(14) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.22(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 121.95(13) . . ?
C3 C4 C17 117.44(13) . . ?
C17 C4 C5 120.59(13) . . ?
C6 C5 C4 120.80(13) . . ?
C14 C5 C4 119.38(13) . . ?
C14 C5 C6 119.81(13) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.49(13) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 119.21(13) . . ?
C6 C7 C32 119.02(13) . . ?
C8 C7 C32 121.72(13) . . ?
C9 C8 C7 121.37(13) . . ?
C9 C8 C13 119.22(13) . . ?
C13 C8 C7 119.41(13) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.50(14) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.37(13) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.43(14) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.85(14) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C14 119.53(13) . . ?
C12 C13 C8 117.01(13) . . ?
C12 C13 C14 123.30(13) . . ?
C5 C14 C13 118.77(13) . . ?
C5 C14 C15 118.68(13) . . ?
C13 C14 C15 122.55(13) . . ?
C16 C15 C14 120.19(13) . . ?
C29 C15 C14 121.01(13) . . ?
C29 C15 C16 118.62(13) . . ?
C15 C16 C17 117.39(13) . . ?
C15 C16 C18 118.60(13) . . ?
C18 C16 C17 123.62(13) . . ?
N1 C17 C4 121.72(13) . . ?
N1 C17 C16 118.15(13) . . ?
C4 C17 C16 119.76(13) . . ?
C16 C18 C19 123.86(13) . . ?
C30 C18 C16 119.06(13) . . ?
C30 C18 C19 117.04(13) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 C18 121.77(14) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 119.1 . . ?
C19 C20 C21 121.83(14) . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 123.01(14) . . ?
C22 C21 C31 119.07(15) . . ?
C31 C21 C20 117.91(14) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.98(15) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.36(15) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.68(15) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 121.81(14) . . ?
C24 C25 C31 119.48(14) . . ?
C31 C25 C26 118.70(14) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.16(14) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.22(14) . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 121.72(13) . . ?
C29 C28 C30 118.91(13) . . ?
C30 C28 C27 119.32(13) . . ?
C15 C29 H29 118.8 . . ?
C28 C29 C15 122.38(13) . . ?
C28 C29 H29 118.8 . . ?
C18 C30 C28 120.01(13) . . ?
C18 C30 C31 121.02(13) . . ?
C31 C30 C28 118.94(13) . . ?
C21 C31 C25 119.41(14) . . ?
C21 C31 C30 119.98(14) . . ?
C30 C31 C25 120.61(14) . . ?
C33 C32 C7 120.28(13) . . ?
C33 C32 C37 118.18(14) . . ?
C37 C32 C7 121.47(13) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.75(13) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.32(14) . . ?
C35 C34 H34 119.3 . . ?
C34 C35 C36 118.02(14) . . ?
C34 C35 C38 120.89(15) . . ?
C36 C35 C38 121.09(14) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 C35 121.05(14) . . ?
C37 C36 H36 119.5 . . ?
C32 C37 H37 119.7 . . ?
C36 C37 C32 120.69(14) . . ?
C36 C37 H37 119.7 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
Cl1 C39 Cl2 109.97(9) . . ?
Cl1 C39 D39 108.6 . . ?
Cl2 C39 D39 108.6 . . ?
Cl3 C39 Cl1 110.65(9) . . ?
Cl3 C39 Cl2 110.26(9) . . ?
Cl3 C39 D39 108.6 . . ?
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 1.328(2) . ?
N1 C17 1.3573(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(2) . ?
C4 C5 1.458(2) . ?
C4 C17 1.417(2) . ?
C5 C6 1.419(2) . ?
C5 C14 1.396(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.369(2) . ?
C7 C8 1.435(2) . ?
C7 C32 1.489(2) . ?
C8 C9 1.414(2) . ?
C8 C13 1.428(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.402(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.421(2) . ?
C13 C14 1.448(2) . ?
C14 C15 1.464(2) . ?
C15 C16 1.422(2) . ?
C15 C29 1.408(2) . ?
C16 C17 1.465(2) . ?
C16 C18 1.438(2) . ?
C18 C19 1.439(2) . ?
C18 C30 1.420(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.356(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.431(2) . ?
C21 C22 1.403(2) . ?
C21 C31 1.420(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(2) . ?
C25 C26 1.439(2) . ?
C25 C31 1.426(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.353(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.440(2) . ?
C28 C29 1.380(2) . ?
C28 C30 1.429(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.426(2) . ?
C32 C33 1.393(2) . ?
C32 C37 1.403(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.392(2) . ?
C35 C36 1.395(2) . ?
C35 C38 1.507(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.390(2) . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
Cl1 C39 1.7644(16) . ?
Cl2 C39 1.7653(16) . ?
Cl3 C39 1.7591(16) . ?
C39 D39 1.0000 . ?
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 -0.2(2) . . . . ?
C1 N1 C17 C4 0.3(2) . . . . ?
C1 N1 C17 C16 -172.62(13) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -178.67(13) . . . . ?
C2 C3 C4 C17 -0.2(2) . . . . ?
C3 C4 C5 C6 4.7(2) . . . . ?
C3 C4 C5 C14 -176.49(13) . . . . ?
C3 C4 C17 N1 -0.1(2) . . . . ?
C3 C4 C17 C16 172.71(12) . . . . ?
C4 C5 C6 C7 176.77(13) . . . . ?
C4 C5 C14 C13 -170.06(12) . . . . ?
C4 C5 C14 C15 10.67(19) . . . . ?
C5 C4 C17 N1 178.34(13) . . . . ?
C5 C4 C17 C16 -8.81(19) . . . . ?
C5 C6 C7 C8 -3.2(2) . . . . ?
C5 C6 C7 C32 179.29(13) . . . . ?
C5 C14 C15 C16 -23.46(19) . . . . ?
C5 C14 C15 C29 151.60(14) . . . . ?
C6 C5 C14 C13 8.7(2) . . . . ?
C6 C5 C14 C15 -170.52(12) . . . . ?
C6 C7 C8 C9 -177.54(13) . . . . ?
C6 C7 C8 C13 1.4(2) . . . . ?
C6 C7 C32 C33 -59.04(19) . . . . ?
C6 C7 C32 C37 117.95(16) . . . . ?
C7 C8 C9 C10 174.50(14) . . . . ?
C7 C8 C13 C12 -170.17(13) . . . . ?
C7 C8 C13 C14 5.31(19) . . . . ?
C7 C32 C33 C34 177.66(13) . . . . ?
C7 C32 C37 C36 -177.09(13) . . . . ?
C8 C7 C32 C33 123.49(15) . . . . ?
C8 C7 C32 C37 -59.51(19) . . . . ?
C8 C9 C10 C11 -2.3(2) . . . . ?
C8 C13 C14 C5 -10.4(2) . . . . ?
C8 C13 C14 C15 168.86(12) . . . . ?
C9 C8 C13 C12 8.80(19) . . . . ?
C9 C8 C13 C14 -175.72(13) . . . . ?
C9 C10 C11 C12 4.5(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C8 -6.9(2) . . . . ?
C11 C12 C13 C14 177.85(13) . . . . ?
C12 C13 C14 C5 164.80(13) . . . . ?
C12 C13 C14 C15 -16.0(2) . . . . ?
C13 C8 C9 C10 -4.5(2) . . . . ?
C13 C14 C15 C16 157.30(13) . . . . ?
C13 C14 C15 C29 -27.6(2) . . . . ?
C14 C5 C6 C7 -2.0(2) . . . . ?
C14 C15 C16 C17 19.51(19) . . . . ?
C14 C15 C16 C18 -167.34(12) . . . . ?
C14 C15 C29 C28 177.49(13) . . . . ?
C15 C16 C17 N1 169.57(12) . . . . ?
C15 C16 C17 C4 -3.53(19) . . . . ?
C15 C16 C18 C19 162.20(13) . . . . ?
C15 C16 C18 C30 -15.44(19) . . . . ?
C16 C15 C29 C28 -7.4(2) . . . . ?
C16 C18 C19 C20 177.54(13) . . . . ?
C16 C18 C30 C28 3.2(2) . . . . ?
C16 C18 C30 C31 -174.72(12) . . . . ?
C17 N1 C1 C2 -0.2(2) . . . . ?
C17 C4 C5 C6 -173.70(12) . . . . ?
C17 C4 C5 C14 5.1(2) . . . . ?
C17 C16 C18 C19 -25.1(2) . . . . ?
C17 C16 C18 C30 157.24(13) . . . . ?
C18 C16 C17 N1 -3.2(2) . . . . ?
C18 C16 C17 C4 -176.30(13) . . . . ?
C18 C19 C20 C21 -1.2(2) . . . . ?
C18 C30 C31 C21 -4.3(2) . . . . ?
C18 C30 C31 C25 175.23(13) . . . . ?
C19 C18 C30 C28 -174.58(13) . . . . ?
C19 C18 C30 C31 7.5(2) . . . . ?
C19 C20 C21 C22 -175.42(15) . . . . ?
C19 C20 C21 C31 4.6(2) . . . . ?
C20 C21 C22 C23 179.96(16) . . . . ?
C20 C21 C31 C25 178.67(13) . . . . ?
C20 C21 C31 C30 -1.8(2) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C21 C31 C25 -1.3(2) . . . . ?
C22 C21 C31 C30 178.21(14) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 179.49(16) . . . . ?
C23 C24 C25 C31 -1.3(2) . . . . ?
C24 C25 C26 C27 178.81(15) . . . . ?
C24 C25 C31 C21 2.0(2) . . . . ?
C24 C25 C31 C30 -177.55(14) . . . . ?
C25 C26 C27 C28 0.2(2) . . . . ?
C26 C25 C31 C21 -178.75(13) . . . . ?
C26 C25 C31 C30 1.7(2) . . . . ?
C26 C27 C28 C29 176.17(14) . . . . ?
C26 C27 C28 C30 -1.2(2) . . . . ?
C27 C28 C29 C15 177.61(13) . . . . ?
C27 C28 C30 C18 -175.52(13) . . . . ?
C27 C28 C30 C31 2.5(2) . . . . ?
C28 C30 C31 C21 177.75(13) . . . . ?
C28 C30 C31 C25 -2.7(2) . . . . ?
C29 C15 C16 C17 -155.67(13) . . . . ?
C29 C15 C16 C18 17.48(19) . . . . ?
C29 C28 C30 C18 7.0(2) . . . . ?
C29 C28 C30 C31 -175.02(13) . . . . ?
C30 C18 C19 C20 -4.8(2) . . . . ?
C30 C28 C29 C15 -5.0(2) . . . . ?
C31 C21 C22 C23 -0.1(3) . . . . ?
C31 C25 C26 C27 -0.4(2) . . . . ?
C32 C7 C8 C9 -0.1(2) . . . . ?
C32 C7 C8 C13 178.87(12) . . . . ?
C32 C33 C34 C35 -0.7(2) . . . . ?
C33 C32 C37 C36 0.0(2) . . . . ?
C33 C34 C35 C36 0.3(2) . . . . ?
C33 C34 C35 C38 179.99(14) . . . . ?
C34 C35 C36 C37 0.2(2) . . . . ?
C35 C36 C37 C32 -0.4(2) . . . . ?
C37 C32 C33 C34 0.6(2) . . . . ?
C38 C35 C36 C37 -179.45(14) . . . . ?
