#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/20/4032050.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_4032050
loop_
_publ_author_name
'Etheridge, Forrest S.'
'Fernando, Roshan J.'
'Pejić, Sandra'
'Zeller, Matthias'
'Sauvé, Geneviève'
_publ_section_title
;
 Synthesis and characterization of fluorinated azadipyrromethene complexes
 as acceptors for organic photovoltaics.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1925
_journal_page_last               1938
_journal_paper_doi               10.3762/bjoc.12.182
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C96 H56 F4 N6 Zn, C H2 Cl2'
_chemical_formula_sum            'C97 H58 Cl2 F4 N6 Zn'
_chemical_formula_weight         1519.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.670(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.926(2)
_cell_length_b                   17.636(2)
_cell_length_c                   18.914(2)
_cell_measurement_reflns_used    66194
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.237
_cell_measurement_theta_min      4.056
_cell_volume                     7298.8(13)
_computing_cell_refinement       'HKL3000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_reduction        'HKL3000 (Otwinowski & Minor, 1997)'
_computing_structure_refinement
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type
'Rigaku Rapid II curved image plate diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            66194
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.237
_diffrn_reflns_theta_min         4.056
_diffrn_source                   'microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_T_max  0.720
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             3128
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.00067(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²+22.5412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6710
_reflns_number_total             6973
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1860-5397-12-182-S2.cif
_cod_data_source_block           FSE-2-70-5
_cod_depositor_comments          'Adding full bibliography for 4032050.cif.'
_cod_database_code               4032050
_shelx_shelxl_version_number     2014/7
_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   0.592
_shelx_estimated_absorpt_t_max   0.720
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57881(10) 0.38554(12) 0.22738(12) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.62403(10) 0.34164(12) 0.26709(12) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.64577(10) 0.38639(12) 0.32454(11) 0.0186(4) Uani 1 1 d . . . . .
C4 C 0.61159(10) 0.45543(12) 0.31892(11) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.58362(10) 0.57291(12) 0.36893(11) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.59958(10) 0.63729(12) 0.41330(12) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.55353(10) 0.69063(12) 0.39889(11) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.50876(10) 0.65568(12) 0.35063(11) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.54197(10) 0.36344(13) 0.16293(12) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.52774(11) 0.41606(14) 0.10938(13) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.5439 0.4660 0.1133 0.030 Uiso 1 1 calc R U . . .
C11 C 0.49004(12) 0.39619(15) 0.04998(13) 0.0283(5) Uani 1 1 d . . . . .
H11 H 0.4809 0.4322 0.0135 0.034 Uiso 1 1 calc R U . . .
C12 C 0.46592(11) 0.32320(15) 0.04453(13) 0.0284(5) Uani 1 1 d . . . . .
H12 H 0.4397 0.3096 0.0046 0.034 Uiso 1 1 calc R U . . .
C13 C 0.48012(11) 0.27051(14) 0.09722(13) 0.0265(5) Uani 1 1 d . . . . .
H13 H 0.4636 0.2208 0.0933 0.032 Uiso 1 1 calc R U . . .
C14 C 0.51836(11) 0.28992(13) 0.15570(13) 0.0236(5) Uani 1 1 d . . . . .
H14 H 0.5286 0.2530 0.1911 0.028 Uiso 1 1 calc R U . . .
C15 C 0.64145(10) 0.26559(12) 0.25311(12) 0.0189(4) Uani 1 1 d . . . . .
C16 C 0.65816(10) 0.20114(13) 0.24640(12) 0.0213(5) Uani 1 1 d . . . . .
C17 C 0.67976(10) 0.12467(12) 0.24662(12) 0.0204(5) Uani 1 1 d . . . . .
C18 C 0.68293(12) 0.08214(14) 0.18482(13) 0.0277(5) Uani 1 1 d . . . . .
H18 H 0.6704 0.1039 0.1403 0.033 Uiso 1 1 calc R U . . .
C19 C 0.70436(13) 0.00789(14) 0.18814(14) 0.0330(6) Uani 1 1 d . . . . .
H19 H 0.7067 -0.0207 0.1459 0.040 Uiso 1 1 calc R U . . .
C20 C 0.72222(13) -0.02428(14) 0.25267(15) 0.0335(6) Uani 1 1 d . . . . .
H20 H 0.7366 -0.0751 0.2547 0.040 Uiso 1 1 calc R U . . .
C21 C 0.71926(13) 0.01732(14) 0.31445(15) 0.0329(6) Uani 1 1 d . . . . .
H21 H 0.7316 -0.0049 0.3589 0.039 Uiso 1 1 calc R U . . .
C22 C 0.69831(11) 0.09125(14) 0.31130(13) 0.0266(5) Uani 1 1 d . . . . .
H22 H 0.6965 0.1197 0.3538 0.032 Uiso 1 1 calc R U . . .
C23 C 0.69330(10) 0.36687(12) 0.37938(12) 0.0188(4) Uani 1 1 d . . . . .
C24 C 0.74218(10) 0.32020(12) 0.36363(12) 0.0205(5) Uani 1 1 d . . . . .
H24 H 0.7442 0.3012 0.3168 0.025 Uiso 1 1 calc R U . . .
C25 C 0.78789(10) 0.30094(13) 0.41476(12) 0.0222(5) Uani 1 1 d . . . . .
H25 H 0.8211 0.2695 0.4035 0.027 Uiso 1 1 calc R U . . .
C26 C 0.78364(10) 0.32868(12) 0.48207(12) 0.0218(5) Uani 1 1 d . . . . .
C27 C 0.73685(11) 0.37504(13) 0.50031(13) 0.0251(5) Uani 1 1 d . . . . .
H27 H 0.7355 0.3936 0.5473 0.030 Uiso 1 1 calc R U . . .
C28 C 0.69159(11) 0.39431(13) 0.44898(12) 0.0232(5) Uani 1 1 d . . . . .
H28 H 0.6590 0.4264 0.4610 0.028 Uiso 1 1 calc R U . . .
C29 C 0.65313(10) 0.64396(12) 0.46344(12) 0.0189(4) Uani 1 1 d . . . . .
C30 C 0.70899(11) 0.61055(13) 0.45031(12) 0.0240(5) Uani 1 1 d . . . . .
H30 H 0.7130 0.5839 0.4072 0.029 Uiso 1 1 calc R U . . .
C31 C 0.75887(11) 0.61567(14) 0.49940(13) 0.0267(5) Uani 1 1 d . . . . .
H31 H 0.7968 0.5926 0.4904 0.032 Uiso 1 1 calc R U . . .
C32 C 0.75197(11) 0.65500(14) 0.56134(13) 0.0247(5) Uani 1 1 d . . . . .
C33 C 0.69783(11) 0.68866(14) 0.57676(13) 0.0266(5) Uani 1 1 d . . . . .
H33 H 0.6943 0.7149 0.6201 0.032 Uiso 1 1 calc R U . . .
C34 C 0.64841(11) 0.68322(13) 0.52723(12) 0.0226(5) Uani 1 1 d . . . . .
H34 H 0.6108 0.7065 0.5368 0.027 Uiso 1 1 calc R U . . .
C35 C 0.55299(10) 0.76629(13) 0.42503(12) 0.0207(5) Uani 1 1 d . . . . .
C36 C 0.55907(11) 0.82998(14) 0.44701(13) 0.0249(5) Uani 1 1 d . . . . .
C37 C 0.56937(10) 0.90528(13) 0.47369(14) 0.0249(5) Uani 1 1 d . . . . .
C38 C 0.55922(12) 0.92347(15) 0.54338(15) 0.0318(6) Uani 1 1 d . . . . .
H38 H 0.5454 0.8855 0.5742 0.038 Uiso 1 1 calc R U . . .
C39 C 0.56921(13) 0.99692(16) 0.56845(16) 0.0363(6) Uani 1 1 d . . . . .
H39 H 0.5621 1.0088 0.6162 0.044 Uiso 1 1 calc R U . . .
C40 C 0.58937(12) 1.05243(14) 0.52443(16) 0.0329(6) Uani 1 1 d . . . . .
H40 H 0.5957 1.1026 0.5416 0.039 Uiso 1 1 calc R U . . .
C41 C 0.60030(12) 1.03483(15) 0.45515(16) 0.0336(6) Uani 1 1 d . . . . .
H41 H 0.6147 1.0730 0.4249 0.040 Uiso 1 1 calc R U . . .
C42 C 0.59049(12) 0.96218(14) 0.42968(15) 0.0307(6) Uani 1 1 d . . . . .
H42 H 0.5981 0.9507 0.3820 0.037 Uiso 1 1 calc R U . . .
C43 C 0.45004(10) 0.68597(13) 0.32116(12) 0.0203(5) Uani 1 1 d . . . . .
C44 C 0.44260(11) 0.76285(13) 0.30476(13) 0.0242(5) Uani 1 1 d . . . . .
H44 H 0.4739 0.7979 0.3191 0.029 Uiso 1 1 calc R U . . .
C45 C 0.38983(12) 0.78826(15) 0.26762(14) 0.0311(6) Uani 1 1 d . . . . .
H45 H 0.3854 0.8404 0.2558 0.037 Uiso 1 1 calc R U . . .
C46 C 0.34356(12) 0.73748(16) 0.24783(13) 0.0313(6) Uani 1 1 d . . . . .
H46 H 0.3082 0.7546 0.2209 0.038 Uiso 1 1 calc R U . . .
C47 C 0.34879(11) 0.66201(15) 0.26713(13) 0.0283(5) Uani 1 1 d . . . . .
H47 H 0.3163 0.6277 0.2552 0.034 Uiso 1 1 calc R U . . .
C48 C 0.40153(10) 0.63655(13) 0.30391(12) 0.0225(5) Uani 1 1 d . . . . .
H48 H 0.4048 0.5848 0.3176 0.027 Uiso 1 1 calc R U . . .
N1 N 0.57166(8) 0.45292(10) 0.25823(10) 0.0178(4) Uani 1 1 d . . . . .
N2 N 0.61844(8) 0.51212(10) 0.36495(10) 0.0175(4) Uani 1 1 d . . . . .
N3 N 0.52724(8) 0.58619(10) 0.33271(10) 0.0182(4) Uani 1 1 d . . . . .
F1 F 0.82770(6) 0.30833(8) 0.53281(7) 0.0279(3) Uani 1 1 d . . . . .
F2 F 0.80024(7) 0.65943(9) 0.60992(8) 0.0345(4) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.52233(2) 0.2500 0.01720(13) Uani 1 2 d S T P . .
C49 C 0.5306(3) 0.0396(3) 0.2684(4) 0.0405(13) Uani 0.5 1 d . . P A -1
H49A H 0.5381 0.0473 0.3201 0.049 Uiso 0.5 1 calc R U P A -1
H49B H 0.5698 0.0456 0.2457 0.049 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.4983(4) -0.05472(7) 0.2500(5) 0.0559(6) Uani 0.5 1 d . . P A -1
Cl2 Cl 0.47710(8) 0.10409(8) 0.23356(10) 0.0539(4) Uani 0.5 1 d . . P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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'
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
N1 C1 C2 110.37(19) . .
N1 C1 C9 121.6(2) . .
C2 C1 C9 128.1(2) . .
C3 C2 C15 126.3(2) . .
C3 C2 C1 106.96(19) . .
C15 C2 C1 126.6(2) . .
C2 C3 C4 105.74(19) . .
C2 C3 C23 127.5(2) . .
C4 C3 C23 126.8(2) . .
N2 C4 N1 126.89(19) . .
N2 C4 C3 123.8(2) . .
N1 C4 C3 109.36(18) . .
N2 C5 N3 127.28(19) . .
N2 C5 C6 123.6(2) . .
N3 C5 C6 109.17(18) . .
C7 C6 C5 105.78(19) . .
C7 C6 C29 127.8(2) . .
C5 C6 C29 126.46(19) . .
C6 C7 C35 125.9(2) . .
C6 C7 C8 106.96(19) . .
C35 C7 C8 127.1(2) . .
N3 C8 C7 110.34(18) . .
N3 C8 C43 120.50(19) . .
C7 C8 C43 129.2(2) . .
C10 C9 C14 118.8(2) . .
C10 C9 C1 120.7(2) . .
C14 C9 C1 120.4(2) . .
C9 C10 C11 120.7(2) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C12 C11 C10 119.6(2) . .
C12 C11 H11 120.2 . .
C10 C11 H11 120.2 . .
C13 C12 C11 120.0(2) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C14 120.3(2) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C13 C14 C9 120.5(2) . .
C13 C14 H14 119.8 . .
C9 C14 H14 119.8 . .
C16 C15 C2 175.1(2) . .
C15 C16 C17 173.7(2) . .
C18 C17 C22 118.7(2) . .
C18 C17 C16 122.6(2) . .
C22 C17 C16 118.6(2) . .
C19 C18 C17 120.2(2) . .
C19 C18 H18 119.9 . .
C17 C18 H18 119.9 . .
C20 C19 C18 120.2(2) . .
C20 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
C19 C20 C21 120.2(2) . .
C19 C20 H20 119.9 . .
C21 C20 H20 119.9 . .
C22 C21 C20 119.8(2) . .
C22 C21 H21 120.1 . .
C20 C21 H21 120.1 . .
C21 C22 C17 120.9(2) . .
C21 C22 H22 119.5 . .
C17 C22 H22 119.5 . .
C24 C23 C28 118.0(2) . .
C24 C23 C3 120.5(2) . .
C28 C23 C3 121.5(2) . .
C25 C24 C23 121.6(2) . .
C25 C24 H24 119.2 . .
C23 C24 H24 119.2 . .
C26 C25 C24 118.0(2) . .
C26 C25 H25 121.0 . .
C24 C25 H25 121.0 . .
F1 C26 C25 118.1(2) . .
F1 C26 C27 119.1(2) . .
C25 C26 C27 122.8(2) . .
C26 C27 C28 118.9(2) . .
C26 C27 H27 120.6 . .
C28 C27 H27 120.6 . .
C27 C28 C23 120.7(2) . .
C27 C28 H28 119.6 . .
C23 C28 H28 119.6 . .
C30 C29 C34 118.4(2) . .
C30 C29 C6 121.8(2) . .
C34 C29 C6 119.8(2) . .
C31 C30 C29 121.0(2) . .
C31 C30 H30 119.5 . .
C29 C30 H30 119.5 . .
C32 C31 C30 118.4(2) . .
C32 C31 H31 120.8 . .
C30 C31 H31 120.8 . .
F2 C32 C33 118.5(2) . .
F2 C32 C31 118.7(2) . .
C33 C32 C31 122.7(2) . .
C32 C33 C34 118.3(2) . .
C32 C33 H33 120.9 . .
C34 C33 H33 120.9 . .
C33 C34 C29 121.2(2) . .
C33 C34 H34 119.4 . .
C29 C34 H34 119.4 . .
C36 C35 C7 173.1(2) . .
C35 C36 C37 177.3(3) . .
C38 C37 C42 118.5(2) . .
C38 C37 C36 121.1(2) . .
C42 C37 C36 120.3(2) . .
C37 C38 C39 120.5(2) . .
C37 C38 H38 119.8 . .
C39 C38 H38 119.8 . .
C40 C39 C38 120.4(3) . .
C40 C39 H39 119.8 . .
C38 C39 H39 119.8 . .
C39 C40 C41 119.7(2) . .
C39 C40 H40 120.1 . .
C41 C40 H40 120.1 . .
C42 C41 C40 120.4(3) . .
C42 C41 H41 119.8 . .
C40 C41 H41 119.8 . .
C41 C42 C37 120.5(3) . .
C41 C42 H42 119.8 . .
C37 C42 H42 119.8 . .
C48 C43 C44 118.5(2) . .
C48 C43 C8 119.8(2) . .
C44 C43 C8 121.5(2) . .
C45 C44 C43 120.4(2) . .
C45 C44 H44 119.8 . .
C43 C44 H44 119.8 . .
C46 C45 C44 120.0(2) . .
C46 C45 H45 120.0 . .
C44 C45 H45 120.0 . .
C47 C46 C45 120.2(2) . .
C47 C46 H46 119.9 . .
C45 C46 H46 119.9 . .
C46 C47 C48 119.8(2) . .
C46 C47 H47 120.1 . .
C48 C47 H47 120.1 . .
C47 C48 C43 120.9(2) . .
C47 C48 H48 119.6 . .
C43 C48 H48 119.6 . .
C1 N1 C4 107.53(18) . .
C1 N1 Zn1 128.79(15) . .
C4 N1 Zn1 119.62(14) . .
C5 N2 C4 127.36(19) . .
C8 N3 C5 107.58(18) . .
C8 N3 Zn1 129.50(15) . .
C5 N3 Zn1 120.25(14) . .
N3 Zn1 N3 111.00(11) . 2_655
N3 Zn1 N1 95.22(7) . .
N3 Zn1 N1 127.29(7) 2_655 .
N3 Zn1 N1 127.30(7) . 2_655
N3 Zn1 N1 95.22(7) 2_655 2_655
N1 Zn1 N1 104.07(11) . 2_655
Cl2 C49 Cl1 106.1(4) . .
Cl2 C49 H49A 110.5 . .
Cl1 C49 H49A 110.5 . .
Cl2 C49 H49B 110.5 . .
Cl1 C49 H49B 110.5 . .
H49A C49 H49B 108.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.338(3) .
C1 C2 1.432(3) .
C1 C9 1.471(3) .
C2 C3 1.402(3) .
C2 C15 1.424(3) .
C3 C4 1.430(3) .
C3 C23 1.464(3) .
C4 N2 1.328(3) .
C4 N1 1.399(3) .
C5 N2 1.321(3) .
C5 N3 1.394(3) .
C5 C6 1.442(3) .
C6 C7 1.394(3) .
C6 C29 1.466(3) .
C7 C35 1.423(3) .
C7 C8 1.436(3) .
C8 N3 1.341(3) .
C8 C43 1.470(3) .
C9 C10 1.394(3) .
C9 C14 1.400(3) .
C10 C11 1.396(3) .
C10 H10 0.9500 .
C11 C12 1.393(4) .
C11 H11 0.9500 .
C12 C13 1.383(4) .
C12 H12 0.9500 .
C13 C14 1.387(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.203(3) .
C16 C17 1.429(3) .
C17 C18 1.394(3) .
C17 C22 1.395(3) .
C18 C19 1.391(3) .
C18 H18 0.9500 .
C19 C20 1.380(4) .
C19 H19 0.9500 .
C20 C21 1.385(4) .
C20 H20 0.9500 .
C21 C22 1.382(3) .
C21 H21 0.9500 .
C22 H22 0.9500 .
C23 C24 1.398(3) .
C23 C28 1.405(3) .
C24 C25 1.390(3) .
C24 H24 0.9500 .
C25 C26 1.373(3) .
C25 H25 0.9500 .
C26 F1 1.365(3) .
C26 C27 1.373(3) .
C27 C28 1.385(3) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C29 C30 1.396(3) .
C29 C34 1.401(3) .
C30 C31 1.392(3) .
C30 H30 0.9500 .
C31 C32 1.378(3) .
C31 H31 0.9500 .
C32 F2 1.358(3) .
C32 C33 1.375(3) .
C33 C34 1.390(3) .
C33 H33 0.9500 .
C34 H34 0.9500 .
C35 C36 1.202(3) .
C36 C37 1.433(3) .
C37 C38 1.388(4) .
C37 C42 1.401(4) .
C38 C39 1.392(4) .
C38 H38 0.9500 .
C39 C40 1.376(4) .
C39 H39 0.9500 .
C40 C41 1.382(4) .
C40 H40 0.9500 .
C41 C42 1.381(4) .
C41 H41 0.9500 .
C42 H42 0.9500 .
C43 C48 1.397(3) .
C43 C44 1.398(3) .
C44 C45 1.389(4) .
C44 H44 0.9500 .
C45 C46 1.387(4) .
C45 H45 0.9500 .
C46 C47 1.383(4) .
C46 H46 0.9500 .
C47 C48 1.386(3) .
C47 H47 0.9500 .
C48 H48 0.9500 .
N1 Zn1 1.9900(18) .
N3 Zn1 1.9882(18) .
Zn1 N3 1.9882(18) 2_655
Zn1 N1 1.9900(18) 2_655
C49 Cl2 1.734(6) .
C49 Cl1 1.833(7) .
C49 H49A 0.9900 .
C49 H49B 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
N1 C1 C2 C3 -1.0(2)
C9 C1 C2 C3 -179.1(2)
N1 C1 C2 C15 176.1(2)
C9 C1 C2 C15 -2.0(4)
C15 C2 C3 C4 -175.4(2)
C1 C2 C3 C4 1.7(2)
C15 C2 C3 C23 4.3(4)
C1 C2 C3 C23 -178.7(2)
C2 C3 C4 N2 178.8(2)
C23 C3 C4 N2 -0.9(4)
C2 C3 C4 N1 -1.8(2)
C23 C3 C4 N1 178.5(2)
N2 C5 C6 C7 176.1(2)
N3 C5 C6 C7 -3.8(2)
N2 C5 C6 C29 -4.4(3)
N3 C5 C6 C29 175.6(2)
C5 C6 C7 C35 -173.3(2)
C29 C6 C7 C35 7.2(4)
C5 C6 C7 C8 4.2(2)
C29 C6 C7 C8 -175.3(2)
C6 C7 C8 N3 -3.3(2)
C35 C7 C8 N3 174.2(2)
C6 C7 C8 C43 177.1(2)
C35 C7 C8 C43 -5.4(4)
N1 C1 C9 C10 39.0(3)
C2 C1 C9 C10 -143.1(2)
N1 C1 C9 C14 -138.2(2)
C2 C1 C9 C14 39.7(3)
C14 C9 C10 C11 0.8(3)
C1 C9 C10 C11 -176.5(2)
C9 C10 C11 C12 0.6(4)
C10 C11 C12 C13 -1.0(4)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C9 1.4(4)
C10 C9 C14 C13 -1.8(3)
C1 C9 C14 C13 175.5(2)
C22 C17 C18 C19 -0.1(4)
C16 C17 C18 C19 180.0(2)
C17 C18 C19 C20 0.4(4)
C18 C19 C20 C21 -0.4(4)
C19 C20 C21 C22 0.0(4)
C20 C21 C22 C17 0.3(4)
C18 C17 C22 C21 -0.2(4)
C16 C17 C22 C21 179.7(2)
C2 C3 C23 C24 32.2(3)
C4 C3 C23 C24 -148.2(2)
C2 C3 C23 C28 -148.0(2)
C4 C3 C23 C28 31.6(3)
C28 C23 C24 C25 0.2(3)
C3 C23 C24 C25 179.9(2)
C23 C24 C25 C26 0.5(3)
C24 C25 C26 F1 178.43(19)
C24 C25 C26 C27 -0.9(3)
F1 C26 C27 C28 -178.7(2)
C25 C26 C27 C28 0.6(4)
C26 C27 C28 C23 0.1(4)
C24 C23 C28 C27 -0.5(3)
C3 C23 C28 C27 179.8(2)
C7 C6 C29 C30 -146.5(2)
C5 C6 C29 C30 34.1(3)
C7 C6 C29 C34 35.0(3)
C5 C6 C29 C34 -144.3(2)
C34 C29 C30 C31 0.3(3)
C6 C29 C30 C31 -178.2(2)
C29 C30 C31 C32 -0.4(4)
C30 C31 C32 F2 179.2(2)
C30 C31 C32 C33 0.6(4)
F2 C32 C33 C34 -179.3(2)
C31 C32 C33 C34 -0.7(4)
C32 C33 C34 C29 0.6(4)
C30 C29 C34 C33 -0.4(3)
C6 C29 C34 C33 178.1(2)
C42 C37 C38 C39 0.7(4)
C36 C37 C38 C39 -179.8(2)
C37 C38 C39 C40 -0.1(4)
C38 C39 C40 C41 -0.6(4)
C39 C40 C41 C42 0.7(4)
C40 C41 C42 C37 -0.1(4)
C38 C37 C42 C41 -0.7(4)
C36 C37 C42 C41 179.8(2)
N3 C8 C43 C48 30.6(3)
C7 C8 C43 C48 -149.8(2)
N3 C8 C43 C44 -144.5(2)
C7 C8 C43 C44 35.1(3)
C48 C43 C44 C45 -4.6(3)
C8 C43 C44 C45 170.6(2)
C43 C44 C45 C46 1.3(4)
C44 C45 C46 C47 2.3(4)
C45 C46 C47 C48 -2.6(4)
C46 C47 C48 C43 -0.8(4)
C44 C43 C48 C47 4.3(3)
C8 C43 C48 C47 -170.9(2)
C2 C1 N1 C4 -0.1(2)
C9 C1 N1 C4 178.12(19)
C2 C1 N1 Zn1 -156.90(15)
C9 C1 N1 Zn1 21.3(3)
N2 C4 N1 C1 -179.4(2)
C3 C4 N1 C1 1.2(2)
N2 C4 N1 Zn1 -20.1(3)
C3 C4 N1 Zn1 160.49(14)
N3 C5 N2 C4 10.0(4)
C6 C5 N2 C4 -170.0(2)
N1 C4 N2 C5 10.3(4)
C3 C4 N2 C5 -170.4(2)
C7 C8 N3 C5 0.8(2)
C43 C8 N3 C5 -179.51(19)
C7 C8 N3 Zn1 -160.25(15)
C43 C8 N3 Zn1 19.4(3)
N2 C5 N3 C8 -178.1(2)
C6 C5 N3 C8 1.9(2)
N2 C5 N3 Zn1 -15.0(3)
C6 C5 N3 Zn1 165.03(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094762
