#------------------------------------------------------------------------------
#$Date: 2019-09-18 10:59:51 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233936.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_7233936
loop_
_publ_author_name
'Zhiwen Zheng'
'Qingchen Dong'
'Liao Gou'
'Jian-Hua Su'
'Jinhai Huang'
_publ_section_title
;
 Novel hole transport materials based on
 N,N'-disubstituted-dihydrophenazine derivatives for electroluminescent
 diodes
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9858
_journal_page_last               9865
_journal_paper_doi               10.1039/C4TC01965B
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C52 H36 Cl2 N4'
_chemical_formula_weight         787.75
_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
_cell_angle_alpha                101.429(4)
_cell_angle_beta                 97.164(5)
_cell_angle_gamma                104.122(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4937(15)
_cell_length_b                   10.0154(16)
_cell_length_c                   21.812(4)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.25
_cell_measurement_theta_min      2.25
_cell_volume                     1938.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19691
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.698
_diffrn_reflns_theta_min         0.969
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         11817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0755
_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)+(0.0947P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2283
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6209
_reflns_number_total             11817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000003.cif
_cod_data_source_block           PCOD1000003
_cod_original_cell_volume        1938.5(6)
_cod_database_code               7233936
_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_min   0.935
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2013-4
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 0.4468(2) -0.2412(2) 0.12632(9) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.4159(2) 0.0285(2) 0.15220(9) 0.0178(4) Uani 1 1 d . . . . .
N3 N 0.8268(3) 0.4957(2) 0.64934(9) 0.0270(5) Uani 1 1 d . . . . .
N4 N 0.8766(2) 0.7062(2) 0.62356(10) 0.0252(5) Uani 1 1 d . . . . .
C1 C 0.5324(3) -0.1367(2) 0.09980(10) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.6238(2) -0.1783(2) 0.05581(10) 0.0170(5) Uani 1 1 d . . . . .
C3 C 0.6259(3) -0.3198(3) 0.03701(11) 0.0193(5) Uani 1 1 d . . . . .
H3 H 0.5681 -0.3893 0.0545 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7103(3) -0.3599(3) -0.00646(12) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.7095 -0.4564 -0.0194 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7967(3) -0.2575(3) -0.03126(11) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.8560 -0.2841 -0.0609 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7967(3) -0.1176(3) -0.01307(11) 0.0234(5) Uani 1 1 d . . . . .
H6 H 0.8572 -0.0490 -0.0301 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7092(3) -0.0743(2) 0.03020(10) 0.0175(5) Uani 1 1 d . . . . .
C8 C 0.7008(2) 0.0710(2) 0.04684(10) 0.0167(5) Uani 1 1 d . . . . .
C9 C 0.7858(3) 0.1801(3) 0.02364(11) 0.0221(5) Uani 1 1 d . . . . .
H9 H 0.8523 0.1594 -0.0036 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7734(3) 0.3161(3) 0.03993(11) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.8326 0.3884 0.0244 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6759(3) 0.3489(3) 0.07865(12) 0.0244(5) Uani 1 1 d . . . . .
H11 H 0.6688 0.4433 0.0896 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5899(3) 0.2455(3) 0.10112(11) 0.0209(5) Uani 1 1 d . . . . .
H12 H 0.5212 0.2683 0.1267 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6019(2) 0.1056(2) 0.08679(10) 0.0168(4) Uani 1 1 d . . . . .
C14 C 0.5192(2) -0.0021(2) 0.11326(10) 0.0168(4) Uani 1 1 d . . . . .
C15 C 0.2869(3) -0.0881(3) 0.14218(10) 0.0182(5) Uani 1 1 d . . . . .
C16 C 0.1470(3) -0.0684(3) 0.14076(11) 0.0231(5) Uani 1 1 d . . . . .
H16 H 0.1348 0.0242 0.1454 0.028 Uiso 1 1 calc R U . . .
C17 C 0.0252(3) -0.1836(3) 0.13254(12) 0.0278(6) Uani 1 1 d . . . . .
H17 H -0.0704 -0.1698 0.1324 0.033 Uiso 1 1 calc R U . . .
C18 C 0.0424(3) -0.3188(3) 0.12448(13) 0.0318(6) Uani 1 1 d . . . . .
H18 H -0.0410 -0.3972 0.1203 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1809(3) -0.3406(3) 0.12247(12) 0.0253(5) Uani 1 1 d . . . . .
H19 H 0.1913 -0.4341 0.1147 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3042(3) -0.2253(3) 0.13192(10) 0.0190(5) Uani 1 1 d . . . . .
C21 C 0.5244(3) -0.2924(3) 0.17354(11) 0.0229(5) Uani 1 1 d . . . . .
C22 C 0.6591(4) -0.2096(4) 0.2085(2) 0.0705(15) Uani 1 1 d . . . . .
H22 H 0.7005 -0.1185 0.2017 0.085 Uiso 1 1 calc R U . . .
C23 C 0.7349(5) -0.2598(5) 0.2543(2) 0.099(2) Uani 1 1 d . . . . .
H23 H 0.8270 -0.2015 0.2788 0.119 Uiso 1 1 calc R U . . .
C24 C 0.6789(5) -0.3901(4) 0.26396(18) 0.0631(12) Uani 1 1 d . . . . .
H24 H 0.7322 -0.4245 0.2942 0.076 Uiso 1 1 calc R U . . .
C25 C 0.5452(4) -0.4712(3) 0.22976(14) 0.0414(8) Uani 1 1 d . . . . .
H25 H 0.5035 -0.5615 0.2373 0.050 Uiso 1 1 calc R U . . .
C26 C 0.4688(4) -0.4235(3) 0.18400(13) 0.0346(7) Uani 1 1 d . . . . .
H26 H 0.3768 -0.4827 0.1597 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4698(3) 0.1161(2) 0.21464(10) 0.0169(4) Uani 1 1 d . . . . .
C28 C 0.3753(3) 0.1557(3) 0.25426(11) 0.0217(5) Uani 1 1 d . . . . .
H28 H 0.2718 0.1269 0.2389 0.026 Uiso 1 1 calc R U . . .
C29 C 0.4305(3) 0.2366(3) 0.31596(11) 0.0229(5) Uani 1 1 d . . . . .
H29 H 0.3634 0.2605 0.3422 0.027 Uiso 1 1 calc R U . . .
C30 C 0.5803(3) 0.2835(3) 0.34043(10) 0.0202(5) Uani 1 1 d . . . . .
C31 C 0.6745(3) 0.2500(3) 0.29984(11) 0.0256(5) Uani 1 1 d . . . . .
H31 H 0.7782 0.2843 0.3145 0.031 Uiso 1 1 calc R U . . .
C32 C 0.6210(3) 0.1674(3) 0.23824(11) 0.0250(5) Uani 1 1 d . . . . .
H32 H 0.6886 0.1455 0.2118 0.030 Uiso 1 1 calc R U . . .
C33 C 0.6377(3) 0.3618(3) 0.40741(11) 0.0218(5) Uani 1 1 d . . . . .
C34 C 0.5642(3) 0.3239(3) 0.45580(11) 0.0266(6) Uani 1 1 d . . . . .
H34 H 0.4732 0.2516 0.4452 0.032 Uiso 1 1 calc R U . . .
C35 C 0.6228(3) 0.3906(3) 0.51918(12) 0.0283(6) Uani 1 1 d . . . . .
H35 H 0.5728 0.3621 0.5515 0.034 Uiso 1 1 calc R U . . .
C36 C 0.7539(3) 0.4986(3) 0.53571(11) 0.0232(5) Uani 1 1 d . . . . .
C37 C 0.8249(3) 0.5409(3) 0.48778(12) 0.0284(6) Uani 1 1 d . . . . .
H37 H 0.9128 0.6171 0.4983 0.034 Uiso 1 1 calc R U . . .
C38 C 0.7673(3) 0.4716(3) 0.42448(12) 0.0294(6) Uani 1 1 d . . . . .
H38 H 0.8177 0.5001 0.3922 0.035 Uiso 1 1 calc R U . . .
C39 C 0.8200(3) 0.5697(3) 0.60216(11) 0.0227(5) Uani 1 1 d . . . . .
C40 C 0.8955(3) 0.5968(3) 0.70518(11) 0.0276(6) Uani 1 1 d . . . . .
C41 C 0.9386(3) 0.5832(3) 0.76674(12) 0.0362(7) Uani 1 1 d . . . . .
H41 H 0.9203 0.4934 0.7771 0.043 Uiso 1 1 calc R U . . .
C42 C 1.0091(3) 0.7071(4) 0.81161(12) 0.0358(7) Uani 1 1 d . . . . .
H42 H 1.0381 0.7033 0.8544 0.043 Uiso 1 1 calc R U . . .
C43 C 1.0387(3) 0.8376(3) 0.79586(12) 0.0340(7) Uani 1 1 d . . . . .
H43 H 1.0884 0.9205 0.8282 0.041 Uiso 1 1 calc R U . . .
C44 C 0.9980(3) 0.8511(3) 0.73429(13) 0.0301(6) Uani 1 1 d . . . . .
H44 H 1.0188 0.9409 0.7240 0.036 Uiso 1 1 calc R U . . .
C45 C 0.9256(3) 0.7271(3) 0.68851(11) 0.0252(5) Uani 1 1 d . . . . .
C46 C 0.8029(3) 0.3463(3) 0.64270(12) 0.0302(6) Uani 1 1 d . . . . .
C47 C 0.8800(3) 0.2749(3) 0.60418(13) 0.0361(7) Uani 1 1 d . . . . .
H47 H 0.9430 0.3238 0.5804 0.043 Uiso 1 1 calc R U . . .
C48 C 0.8652(4) 0.1325(4) 0.60037(16) 0.0443(8) Uani 1 1 d . . . . .
H48 H 0.9186 0.0835 0.5744 0.053 Uiso 1 1 calc R U . . .
C49 C 0.7716(4) 0.0620(4) 0.63488(17) 0.0486(9) Uani 1 1 d . . . . .
H49 H 0.7607 -0.0359 0.6324 0.058 Uiso 1 1 calc R U . . .
C50 C 0.6937(4) 0.1339(4) 0.67301(17) 0.0507(9) Uani 1 1 d . . . . .
H50 H 0.6301 0.0851 0.6966 0.061 Uiso 1 1 calc R U . . .
C51 C 0.7084(4) 0.2749(4) 0.67661(14) 0.0407(7) Uani 1 1 d . . . . .
H51 H 0.6540 0.3236 0.7022 0.049 Uiso 1 1 calc R U . . .
C52 C 0.6962(5) 0.9981(5) 0.4316(3) 0.0858(17) Uani 1 1 d . . . . .
H52A H 0.6196 0.9775 0.3932 0.103 Uiso 1 1 calc R U . . .
H52B H 0.6631 1.0513 0.4678 0.103 Uiso 1 1 calc R U . . .
Cl1 Cl 0.86305(10) 1.10275(10) 0.41946(5) 0.0545(3) Uani 1 1 d . . . . .
Cl2 Cl 0.71656(14) 0.83747(13) 0.44775(6) 0.0830(4) 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'
Cl Cl 0.1484 0.1585 '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
C20 N1 C1 113.53(18) . .
C20 N1 C21 119.65(19) . .
C1 N1 C21 117.35(19) . .
C27 N2 C14 118.91(18) . .
C27 N2 C15 118.36(18) . .
C14 N2 C15 112.59(19) . .
C39 N3 C40 105.9(2) . .
C39 N3 C46 128.7(2) . .
C40 N3 C46 123.9(2) . .
C39 N4 C45 105.7(2) . .
C14 C1 N1 119.6(2) . .
C14 C1 C2 121.2(2) . .
N1 C1 C2 119.1(2) . .
C3 C2 C7 119.9(2) . .
C3 C2 C1 121.2(2) . .
C7 C2 C1 118.8(2) . .
C4 C3 C2 121.1(2) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 C5 119.3(2) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 120.4(2) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 121.4(2) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C6 C7 C2 117.8(2) . .
C6 C7 C8 122.1(2) . .
C2 C7 C8 120.0(2) . .
C9 C8 C13 118.0(2) . .
C9 C8 C7 122.5(2) . .
C13 C8 C7 119.4(2) . .
C10 C9 C8 120.8(2) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C9 C10 C11 120.9(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 120.0(2) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.8(2) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C12 C13 C8 119.4(2) . .
C12 C13 C14 121.5(2) . .
C8 C13 C14 119.0(2) . .
C1 C14 N2 118.4(2) . .
C1 C14 C13 121.2(2) . .
N2 C14 C13 120.3(2) . .
C16 C15 C20 120.0(2) . .
C16 C15 N2 121.7(2) . .
C20 C15 N2 118.2(2) . .
C17 C16 C15 120.0(3) . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
C18 C17 C16 120.1(3) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 120.4(2) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C18 C19 C20 119.8(3) . .
C18 C19 H19 120.1 . .
C20 C19 H19 120.1 . .
C19 C20 C15 119.5(2) . .
C19 C20 N1 122.4(2) . .
C15 C20 N1 117.9(2) . .
C26 C21 C22 118.6(2) . .
C26 C21 N1 121.5(2) . .
C22 C21 N1 119.9(2) . .
C21 C22 C23 119.9(3) . .
C21 C22 H22 120.1 . .
C23 C22 H22 120.1 . .
C24 C23 C22 121.0(3) . .
C24 C23 H23 119.5 . .
C22 C23 H23 119.5 . .
C23 C24 C25 119.0(3) . .
C23 C24 H24 120.5 . .
C25 C24 H24 120.5 . .
C24 C25 C26 120.8(3) . .
C24 C25 H25 119.6 . .
C26 C25 H25 119.6 . .
C21 C26 C25 120.7(3) . .
C21 C26 H26 119.6 . .
C25 C26 H26 119.6 . .
C28 C27 C32 117.4(2) . .
C28 C27 N2 122.0(2) . .
C32 C27 N2 120.6(2) . .
C29 C28 C27 120.8(2) . .
C29 C28 H28 119.6 . .
C27 C28 H28 119.6 . .
C30 C29 C28 122.0(2) . .
C30 C29 H29 119.0 . .
C28 C29 H29 119.0 . .
C29 C30 C31 117.0(2) . .
C29 C30 C33 121.7(2) . .
C31 C30 C33 121.3(2) . .
C30 C31 C32 121.7(2) . .
C30 C31 H31 119.2 . .
C32 C31 H31 119.2 . .
C31 C32 C27 121.0(2) . .
C31 C32 H32 119.5 . .
C27 C32 H32 119.5 . .
C38 C33 C34 118.1(2) . .
C38 C33 C30 121.4(2) . .
C34 C33 C30 120.5(2) . .
C35 C34 C33 120.7(2) . .
C35 C34 H34 119.6 . .
C33 C34 H34 119.6 . .
C36 C35 C34 120.6(2) . .
C36 C35 H35 119.7 . .
C34 C35 H35 119.7 . .
C35 C36 C37 119.1(2) . .
C35 C36 C39 122.0(2) . .
C37 C36 C39 118.9(2) . .
C38 C37 C36 120.0(2) . .
C38 C37 H37 120.0 . .
C36 C37 H37 120.0 . .
C33 C38 C37 121.4(2) . .
C33 C38 H38 119.3 . .
C37 C38 H38 119.3 . .
N4 C39 N3 112.9(2) . .
N4 C39 C36 124.8(2) . .
N3 C39 C36 122.2(2) . .
N3 C40 C45 105.9(2) . .
N3 C40 C41 131.2(3) . .
C45 C40 C41 122.8(3) . .
C42 C41 C40 116.3(3) . .
C42 C41 H41 121.9 . .
C40 C41 H41 121.9 . .
C41 C42 C43 121.6(2) . .
C41 C42 H42 119.2 . .
C43 C42 H42 119.2 . .
C42 C43 C44 122.2(3) . .
C42 C43 H43 118.9 . .
C44 C43 H43 118.9 . .
C45 C44 C43 117.0(3) . .
C45 C44 H44 121.5 . .
C43 C44 H44 121.5 . .
C44 C45 N4 130.2(3) . .
C44 C45 C40 120.2(2) . .
N4 C45 C40 109.6(2) . .
C47 C46 C51 120.3(3) . .
C47 C46 N3 119.4(3) . .
C51 C46 N3 120.3(3) . .
C48 C47 C46 120.1(3) . .
C48 C47 H47 120.0 . .
C46 C47 H47 120.0 . .
C47 C48 C49 119.4(3) . .
C47 C48 H48 120.3 . .
C49 C48 H48 120.3 . .
C48 C49 C50 120.3(3) . .
C48 C49 H49 119.9 . .
C50 C49 H49 119.9 . .
C51 C50 C49 120.2(3) . .
C51 C50 H50 119.9 . .
C49 C50 H50 119.9 . .
C50 C51 C46 119.7(3) . .
C50 C51 H51 120.1 . .
C46 C51 H51 120.1 . .
Cl1 C52 Cl2 111.3(3) . .
Cl1 C52 H52A 109.4 . .
Cl2 C52 H52A 109.4 . .
Cl1 C52 H52B 109.4 . .
Cl2 C52 H52B 109.4 . .
H52A C52 H52B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C20 1.418(3) .
N1 C1 1.426(3) .
N1 C21 1.439(3) .
N2 C27 1.421(3) .
N2 C14 1.424(3) .
N2 C15 1.430(3) .
N3 C39 1.386(3) .
N3 C40 1.387(3) .
N3 C46 1.432(4) .
N4 C39 1.305(3) .
N4 C45 1.392(3) .
C1 C14 1.362(3) .
C1 C2 1.439(3) .
C2 C3 1.401(3) .
C2 C7 1.409(3) .
C3 C4 1.378(3) .
C3 H3 0.9500 .
C4 C5 1.392(4) .
C4 H4 0.9500 .
C5 C6 1.378(4) .
C5 H5 0.9500 .
C6 C7 1.407(3) .
C6 H6 0.9500 .
C7 C8 1.453(3) .
C8 C9 1.412(3) .
C8 C13 1.415(3) .
C9 C10 1.375(4) .
C9 H9 0.9500 .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 C12 1.366(3) .
C11 H11 0.9500 .
C12 C13 1.410(3) .
C12 H12 0.9500 .
C13 C14 1.435(3) .
C15 C16 1.387(3) .
C15 C20 1.400(3) .
C16 C17 1.385(4) .
C16 H16 0.9500 .
C17 C18 1.382(4) .
C17 H17 0.9500 .
C18 C19 1.389(4) .
C18 H18 0.9500 .
C19 C20 1.391(3) .
C19 H19 0.9500 .
C21 C26 1.366(4) .
C21 C22 1.376(4) .
C22 C23 1.401(4) .
C22 H22 0.9500 .
C23 C24 1.353(5) .
C23 H23 0.9500 .
C24 C25 1.359(5) .
C24 H24 0.9500 .
C25 C26 1.388(4) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 C28 1.392(3) .
C27 C32 1.394(3) .
C28 C29 1.388(3) .
C28 H28 0.9500 .
C29 C30 1.383(3) .
C29 H29 0.9500 .
C30 C31 1.386(4) .
C30 C33 1.479(3) .
C31 C32 1.390(3) .
C31 H31 0.9500 .
C32 H32 0.9500 .
C33 C38 1.387(4) .
C33 C34 1.399(3) .
C34 C35 1.388(3) .
C34 H34 0.9500 .
C35 C36 1.387(4) .
C35 H35 0.9500 .
C36 C37 1.392(4) .
C36 C39 1.466(3) .
C37 C38 1.391(3) .
C37 H37 0.9500 .
C38 H38 0.9500 .
C40 C45 1.396(4) .
C40 C41 1.397(3) .
C41 C42 1.377(4) .
C41 H41 0.9500 .
C42 C43 1.389(5) .
C42 H42 0.9500 .
C43 C44 1.392(4) .
C43 H43 0.9500 .
C44 C45 1.390(4) .
C44 H44 0.9500 .
C46 C47 1.387(4) .
C46 C51 1.388(4) .
C47 C48 1.383(4) .
C47 H47 0.9500 .
C48 C49 1.388(5) .
C48 H48 0.9500 .
C49 C50 1.390(5) .
C49 H49 0.9500 .
C50 C51 1.370(5) .
C50 H50 0.9500 .
C51 H51 0.9500 .
C52 Cl1 1.755(4) .
C52 Cl2 1.763(5) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
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
C20 N1 C1 C14 35.0(3) . . . .
C21 N1 C1 C14 -111.4(2) . . . .
C20 N1 C1 C2 -140.8(2) . . . .
C21 N1 C1 C2 72.8(3) . . . .
C14 C1 C2 C3 -173.4(2) . . . .
N1 C1 C2 C3 2.3(3) . . . .
C14 C1 C2 C7 4.8(3) . . . .
N1 C1 C2 C7 -179.44(19) . . . .
C7 C2 C3 C4 -0.1(3) . . . .
C1 C2 C3 C4 178.2(2) . . . .
C2 C3 C4 C5 1.1(4) . . . .
C3 C4 C5 C6 -0.7(4) . . . .
C4 C5 C6 C7 -0.7(4) . . . .
C5 C6 C7 C2 1.6(3) . . . .
C5 C6 C7 C8 -176.0(2) . . . .
C3 C2 C7 C6 -1.2(3) . . . .
C1 C2 C7 C6 -179.5(2) . . . .
C3 C2 C7 C8 176.49(19) . . . .
C1 C2 C7 C8 -1.8(3) . . . .
C6 C7 C8 C9 -3.6(3) . . . .
C2 C7 C8 C9 178.76(19) . . . .
C6 C7 C8 C13 175.1(2) . . . .
C2 C7 C8 C13 -2.5(3) . . . .
C13 C8 C9 C10 0.5(3) . . . .
C7 C8 C9 C10 179.3(2) . . . .
C8 C9 C10 C11 -1.0(3) . . . .
C9 C10 C11 C12 -0.2(4) . . . .
C10 C11 C12 C13 1.8(3) . . . .
C11 C12 C13 C8 -2.2(3) . . . .
C11 C12 C13 C14 176.0(2) . . . .
C9 C8 C13 C12 1.0(3) . . . .
C7 C8 C13 C12 -177.78(19) . . . .
C9 C8 C13 C14 -177.24(19) . . . .
C7 C8 C13 C14 4.0(3) . . . .
N1 C1 C14 N2 -1.9(3) . . . .
C2 C1 C14 N2 173.86(19) . . . .
N1 C1 C14 C13 -179.12(19) . . . .
C2 C1 C14 C13 -3.4(3) . . . .
C27 N2 C14 C1 110.4(2) . . . .
C15 N2 C14 C1 -34.4(3) . . . .
C27 N2 C14 C13 -72.3(3) . . . .
C15 N2 C14 C13 142.9(2) . . . .
C12 C13 C14 C1 -179.3(2) . . . .
C8 C13 C14 C1 -1.1(3) . . . .
C12 C13 C14 N2 3.5(3) . . . .
C8 C13 C14 N2 -178.28(19) . . . .
C27 N2 C15 C16 74.9(3) . . . .
C14 N2 C15 C16 -140.0(2) . . . .
C27 N2 C15 C20 -106.8(2) . . . .
C14 N2 C15 C20 38.2(3) . . . .
C20 C15 C16 C17 3.4(3) . . . .
N2 C15 C16 C17 -178.4(2) . . . .
C15 C16 C17 C18 -1.3(4) . . . .
C16 C17 C18 C19 -2.1(4) . . . .
C17 C18 C19 C20 3.4(4) . . . .
C18 C19 C20 C15 -1.2(3) . . . .
C18 C19 C20 N1 -175.8(2) . . . .
C16 C15 C20 C19 -2.2(3) . . . .
N2 C15 C20 C19 179.6(2) . . . .
C16 C15 C20 N1 172.7(2) . . . .
N2 C15 C20 N1 -5.6(3) . . . .
C1 N1 C20 C19 144.1(2) . . . .
C21 N1 C20 C19 -70.4(3) . . . .
C1 N1 C20 C15 -30.6(3) . . . .
C21 N1 C20 C15 115.0(2) . . . .
C20 N1 C21 C26 61.2(3) . . . .
C1 N1 C21 C26 -154.6(3) . . . .
C20 N1 C21 C22 -119.9(4) . . . .
C1 N1 C21 C22 24.3(4) . . . .
C26 C21 C22 C23 -0.8(7) . . . .
N1 C21 C22 C23 -179.7(5) . . . .
C21 C22 C23 C24 1.1(9) . . . .
C22 C23 C24 C25 -1.7(9) . . . .
C23 C24 C25 C26 2.1(7) . . . .
C22 C21 C26 C25 1.1(5) . . . .
N1 C21 C26 C25 -180.0(3) . . . .
C24 C25 C26 C21 -1.8(5) . . . .
C14 N2 C27 C28 177.0(2) . . . .
C15 N2 C27 C28 -40.2(3) . . . .
C14 N2 C27 C32 -2.2(3) . . . .
C15 N2 C27 C32 140.6(2) . . . .
C32 C27 C28 C29 -3.4(4) . . . .
N2 C27 C28 C29 177.3(2) . . . .
C27 C28 C29 C30 1.2(4) . . . .
C28 C29 C30 C31 2.0(4) . . . .
C28 C29 C30 C33 -176.1(2) . . . .
C29 C30 C31 C32 -3.0(4) . . . .
C33 C30 C31 C32 175.2(2) . . . .
C30 C31 C32 C27 0.7(4) . . . .
C28 C27 C32 C31 2.5(4) . . . .
N2 C27 C32 C31 -178.2(2) . . . .
C29 C30 C33 C38 -143.3(3) . . . .
C31 C30 C33 C38 38.7(4) . . . .
C29 C30 C33 C34 38.6(4) . . . .
C31 C30 C33 C34 -139.4(3) . . . .
C38 C33 C34 C35 -2.6(4) . . . .
C30 C33 C34 C35 175.6(2) . . . .
C33 C34 C35 C36 1.5(4) . . . .
C34 C35 C36 C37 1.0(4) . . . .
C34 C35 C36 C39 -179.0(3) . . . .
C35 C36 C37 C38 -2.4(4) . . . .
C39 C36 C37 C38 177.7(3) . . . .
C34 C33 C38 C37 1.2(4) . . . .
C30 C33 C38 C37 -176.9(3) . . . .
C36 C37 C38 C33 1.2(4) . . . .
C45 N4 C39 N3 0.4(3) . . . .
C45 N4 C39 C36 179.8(2) . . . .
C40 N3 C39 N4 -0.5(3) . . . .
C46 N3 C39 N4 -166.8(3) . . . .
C40 N3 C39 C36 -179.9(2) . . . .
C46 N3 C39 C36 13.9(4) . . . .
C35 C36 C39 N4 -136.7(3) . . . .
C37 C36 C39 N4 43.3(4) . . . .
C35 C36 C39 N3 42.6(4) . . . .
C37 C36 C39 N3 -137.4(3) . . . .
C39 N3 C40 C45 0.4(3) . . . .
C46 N3 C40 C45 167.4(3) . . . .
C39 N3 C40 C41 -176.1(3) . . . .
C46 N3 C40 C41 -9.1(5) . . . .
N3 C40 C41 C42 178.2(3) . . . .
C45 C40 C41 C42 2.2(4) . . . .
C40 C41 C42 C43 -1.6(5) . . . .
C41 C42 C43 C44 0.6(5) . . . .
C42 C43 C44 C45 0.0(4) . . . .
C43 C44 C45 N4 -177.5(3) . . . .
C43 C44 C45 C40 0.6(4) . . . .
C39 N4 C45 C44 178.1(3) . . . .
C39 N4 C45 C40 -0.2(3) . . . .
N3 C40 C45 C44 -178.6(2) . . . .
C41 C40 C45 C44 -1.7(4) . . . .
N3 C40 C45 N4 -0.2(3) . . . .
C41 C40 C45 N4 176.7(3) . . . .
C39 N3 C46 C47 52.4(4) . . . .
C40 N3 C46 C47 -111.6(3) . . . .
C39 N3 C46 C51 -130.4(3) . . . .
C40 N3 C46 C51 65.7(4) . . . .
C51 C46 C47 C48 -1.3(4) . . . .
N3 C46 C47 C48 176.0(3) . . . .
C46 C47 C48 C49 0.7(5) . . . .
C47 C48 C49 C50 -0.1(5) . . . .
C48 C49 C50 C51 0.2(5) . . . .
C49 C50 C51 C46 -0.9(5) . . . .
C47 C46 C51 C50 1.4(4) . . . .
N3 C46 C51 C50 -175.8(3) . . . .
