#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/68/7116851.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_7116851
loop_
_publ_author_name
'Stephane A. Baudron'
'Herve Ruffin'
'Mir Wais Hosseini'
_publ_section_title
;
 On Zn(II) 2,2'-bisdipyrrin circular helicates
;
_journal_name_full               Chem.Commun.
_journal_page_first              5906
_journal_paper_doi               10.1039/C5cc00724K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C136 H96 N16 O16 Zn4'
_chemical_formula_weight         2471.77
_space_group_IT_number           23
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 2'
_symmetry_space_group_name_H-M   'I 2 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2015-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.3370(6)
_cell_length_b                   19.7279(14)
_cell_length_c                   23.6518(12)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.41
_cell_volume                     7156.2(7)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50642
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            dark-blue
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
;
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.067(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         10481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                7662
_reflns_number_total             10481
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00724k2.cif
_cod_data_source_block           compoundM-6b
_cod_original_sg_symbol_H-M      I222
_cod_database_code               7116851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x, -y, -z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6999(2) 0.70882(13) 0.46975(10) 0.0366(6) Uani 1 1 d .
H1 H 0.6859 0.6901 0.5047 0.044 Uiso 1 1 calc R
C2 C 0.7159(2) 0.67035(15) 0.42081(12) 0.0458(8) Uani 1 1 d .
H2 H 0.7139 0.6234 0.4174 0.055 Uiso 1 1 calc R
C3 C 0.73515(19) 0.71640(14) 0.37918(11) 0.0375(6) Uani 1 1 d .
H3 H 0.7480 0.7065 0.3417 0.045 Uiso 1 1 calc R
C4 C 0.73179(17) 0.78220(13) 0.40387(9) 0.0277(5) Uani 1 1 d .
C5 C 0.76065(15) 0.84216(14) 0.38016(9) 0.0259(5) Uani 1 1 d .
C6 C 0.77211(15) 0.90444(13) 0.40690(9) 0.0242(5) Uani 1 1 d .
C7 C 0.80089(18) 0.96560(12) 0.38060(9) 0.0288(5) Uani 1 1 d .
H7 H 0.8160 0.9708 0.3428 0.035 Uiso 1 1 calc R
C8 C 0.80234(19) 1.01496(12) 0.42068(9) 0.0298(5) Uani 1 1 d .
H8 H 0.8169 1.0603 0.4153 0.036 Uiso 1 1 calc R
C9 C 0.77742(15) 0.98391(12) 0.47221(9) 0.0248(5) Uani 1 1 d .
C10 C 0.78858(17) 0.83915(12) 0.31938(9) 0.0273(5) Uani 1 1 d .
C11 C 0.72903(18) 0.83923(15) 0.27599(10) 0.0372(7) Uani 1 1 d .
H11 H 0.6697 0.8413 0.2840 0.045 Uiso 1 1 calc R
C12 C 0.7575(2) 0.83623(15) 0.21962(10) 0.0402(7) Uani 1 1 d .
H12 H 0.7171 0.8374 0.1903 0.048 Uiso 1 1 calc R
C13 C 0.84445(19) 0.83158(14) 0.20776(10) 0.0336(6) Uani 1 1 d .
C14 C 0.90426(19) 0.83265(15) 0.25115(10) 0.0389(7) Uani 1 1 d .
H14 H 0.9636 0.8303 0.2432 0.047 Uiso 1 1 calc R
C15 C 0.87625(19) 0.83721(15) 0.30660(10) 0.0381(7) Uani 1 1 d .
H15 H 0.9171 0.8390 0.3356 0.046 Uiso 1 1 calc R
C16 C 0.8718(2) 0.82492(15) 0.14722(11) 0.0403(7) Uani 1 1 d .
C17 C 0.9835(3) 0.7845(2) 0.08701(14) 0.0743(12) Uani 1 1 d .
H17A H 0.9487 0.7500 0.0694 0.111 Uiso 1 1 calc R
H17B H 1.0431 0.7699 0.0886 0.111 Uiso 1 1 calc R
H17C H 0.9796 0.8256 0.0654 0.111 Uiso 1 1 calc R
C18 C 0.83193(18) 0.79236(15) 0.59366(11) 0.0346(6) Uani 1 1 d .
H18 H 0.8642 0.7728 0.5647 0.042 Uiso 1 1 calc R
C19 C 0.85934(19) 0.79555(17) 0.65019(11) 0.0416(7) Uani 1 1 d .
H19 H 0.9113 0.7788 0.6649 0.050 Uiso 1 1 calc R
C20 C 0.79452(19) 0.82826(14) 0.67953(10) 0.0360(6) Uani 1 1 d .
H20 H 0.7942 0.8385 0.7179 0.043 Uiso 1 1 calc R
C21 C 0.72802(15) 0.84342(14) 0.63965(9) 0.0265(5) Uani 1 1 d .
C22 C 0.64929(15) 0.87633(13) 0.64943(9) 0.0267(5) Uani 1 1 d .
C23 C 0.58273(16) 0.89102(13) 0.60966(9) 0.0271(5) Uani 1 1 d .
C24 C 0.49760(17) 0.91245(15) 0.62331(10) 0.0325(6) Uani 1 1 d .
H24 H 0.4765 0.9222 0.6593 0.039 Uiso 1 1 calc R
C25 C 0.45193(17) 0.91626(15) 0.57377(10) 0.0335(6) Uani 1 1 d .
H25 H 0.3937 0.9285 0.5698 0.040 Uiso 1 1 calc R
C26 C 0.50914(15) 0.89825(13) 0.53004(9) 0.0274(5) Uani 1 1 d .
C27 C 0.63167(16) 0.90172(13) 0.70835(9) 0.0278(5) Uani 1 1 d .
C28 C 0.63711(18) 0.97074(14) 0.71813(10) 0.0360(6) Uani 1 1 d .
H28 H 0.6462 1.0002 0.6880 0.043 Uiso 1 1 calc R
C29 C 0.6290(2) 0.99641(16) 0.77259(12) 0.0424(7) Uani 1 1 d .
H29 H 0.6335 1.0428 0.7791 0.051 Uiso 1 1 calc R
C30 C 0.61423(17) 0.95208(15) 0.81730(10) 0.0350(6) Uani 1 1 d .
C31 C 0.6058(2) 0.88443(16) 0.80700(10) 0.0452(7) Uani 1 1 d .
H31 H 0.5936 0.8551 0.8367 0.054 Uiso 1 1 calc R
C32 C 0.6152(2) 0.85889(16) 0.75300(10) 0.0418(7) Uani 1 1 d .
H32 H 0.6103 0.8125 0.7468 0.050 Uiso 1 1 calc R
C33 C 0.6100(2) 0.97803(18) 0.87675(11) 0.0465(8) Uani 1 1 d .
C34 C 0.6261(3) 1.0727(2) 0.93614(15) 0.0892(15) Uani 1 1 d .
H34A H 0.5726 1.0617 0.9552 0.134 Uiso 1 1 calc R
H34B H 0.6320 1.1210 0.9337 0.134 Uiso 1 1 calc R
H34C H 0.6744 1.0543 0.9569 0.134 Uiso 1 1 calc R
N1 N 0.70718(14) 0.77482(10) 0.46031(8) 0.0292(4) Uani 1 1 d .
N2 N 0.75950(12) 0.91768(10) 0.46470(7) 0.0224(4) Uani 1 1 d .
N3 N 0.75470(14) 0.82054(11) 0.58666(8) 0.0279(5) Uani 1 1 d .
N4 N 0.58879(12) 0.88270(11) 0.55116(7) 0.0246(4) Uani 1 1 d .
O1 O 0.82857(16) 0.83864(13) 0.10773(8) 0.0592(7) Uani 1 1 d .
O2 O 0.95173(15) 0.79657(14) 0.14394(8) 0.0572(6) Uani 1 1 d .
O3 O 0.5982(2) 0.94247(14) 0.91698(8) 0.0751(8) Uani 1 1 d .
O4 O 0.62482(18) 1.04416(13) 0.87980(9) 0.0628(7) Uani 1 1 d .
Zn1 Zn 0.699198(17) 0.850569(14) 0.514984(9) 0.02494(7) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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_3
N1 C1 C2 112.2(2) .
N1 C1 H1 123.9 .
C2 C1 H1 123.9 .
C3 C2 C1 105.7(2) .
C3 C2 H2 127.1 .
C1 C2 H2 127.1 .
C2 C3 C4 107.5(2) .
C2 C3 H3 126.2 .
C4 C3 H3 126.2 .
C5 C4 N1 124.4(2) .
C5 C4 C3 127.0(2) .
N1 C4 C3 107.9(2) .
C4 C5 C6 127.7(2) .
C4 C5 C10 116.5(2) .
C6 C5 C10 115.7(2) .
C5 C6 N2 126.0(2) .
C5 C6 C7 125.9(2) .
N2 C6 C7 108.0(2) .
C8 C7 C6 107.9(2) .
C8 C7 H7 126.1 .
C6 C7 H7 126.1 .
C7 C8 C9 106.6(2) .
C7 C8 H8 126.7 .
C9 C8 H8 126.7 .
N2 C9 C8 111.17(19) .
N2 C9 C9 122.7(3) 3_576
C8 C9 C9 125.9(3) 3_576
C11 C10 C15 119.0(2) .
C11 C10 C5 121.7(2) .
C15 C10 C5 119.3(2) .
C10 C11 C12 120.2(2) .
C10 C11 H11 119.9 .
C12 C11 H11 119.9 .
C13 C12 C11 120.1(2) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C12 C13 C14 119.8(2) .
C12 C13 C16 118.4(2) .
C14 C13 C16 121.8(3) .
C13 C14 C15 120.1(3) .
C13 C14 H14 120.0 .
C15 C14 H14 120.0 .
C10 C15 C14 120.9(2) .
C10 C15 H15 119.6 .
C14 C15 H15 119.6 .
O1 C16 O2 124.2(3) .
O1 C16 C13 125.5(3) .
O2 C16 C13 110.2(2) .
O2 C17 H17A 109.5 .
O2 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
O2 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
N3 C18 C19 111.7(2) .
N3 C18 H18 124.1 .
C19 C18 H18 124.1 .
C20 C19 C18 106.6(2) .
C20 C19 H19 126.7 .
C18 C19 H19 126.7 .
C19 C20 C21 106.4(2) .
C19 C20 H20 126.8 .
C21 C20 H20 126.8 .
C22 C21 N3 123.8(2) .
C22 C21 C20 127.7(2) .
N3 C21 C20 108.5(2) .
C21 C22 C23 127.6(2) .
C21 C22 C27 117.7(2) .
C23 C22 C27 114.6(2) .
N4 C23 C24 108.9(2) .
N4 C23 C22 125.8(2) .
C24 C23 C22 125.2(2) .
C25 C24 C23 107.1(2) .
C25 C24 H24 126.4 .
C23 C24 H24 126.4 .
C24 C25 C26 107.3(2) .
C24 C25 H25 126.3 .
C26 C25 H25 126.3 .
N4 C26 C25 110.5(2) .
N4 C26 C26 122.4(3) 4_656
C25 C26 C26 127.1(3) 4_656
C32 C27 C28 119.1(2) .
C32 C27 C22 122.6(2) .
C28 C27 C22 118.1(2) .
C27 C28 C29 120.6(2) .
C27 C28 H28 119.7 .
C29 C28 H28 119.7 .
C28 C29 C30 119.3(3) .
C28 C29 H29 120.3 .
C30 C29 H29 120.3 .
C31 C30 C29 119.7(2) .
C31 C30 C33 119.9(3) .
C29 C30 C33 120.4(3) .
C30 C31 C32 120.9(2) .
C30 C31 H31 119.6 .
C32 C31 H31 119.6 .
C27 C32 C31 120.3(3) .
C27 C32 H32 119.8 .
C31 C32 H32 119.8 .
O3 C33 O4 124.0(3) .
O3 C33 C30 123.6(3) .
O4 C33 C30 112.3(3) .
O4 C34 H34A 109.5 .
O4 C34 H34B 109.5 .
H34A C34 H34B 109.5 .
O4 C34 H34C 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C1 N1 C4 106.6(2) .
C1 N1 Zn1 128.77(16) .
C4 N1 Zn1 124.26(17) .
C9 N2 C6 106.29(19) .
C9 N2 Zn1 131.02(15) .
C6 N2 Zn1 121.17(16) .
C18 N3 C21 106.7(2) .
C18 N3 Zn1 128.14(17) .
C21 N3 Zn1 123.01(16) .
C26 N4 C23 106.18(19) .
C26 N4 Zn1 132.63(14) .
C23 N4 Zn1 121.15(15) .
C16 O2 C17 115.2(3) .
C33 O4 C34 115.8(3) .
N1 Zn1 N3 107.79(8) .
N1 Zn1 N4 124.81(9) .
N3 Zn1 N4 95.29(8) .
N1 Zn1 N2 94.73(8) .
N3 Zn1 N2 120.34(8) .
N4 Zn1 N2 115.77(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.326(3) .
C1 C2 1.406(4) .
C1 H1 0.9300 .
C2 C3 1.372(4) .
C2 H2 0.9300 .
C3 C4 1.424(4) .
C3 H3 0.9300 .
C4 C5 1.382(4) .
C4 N1 1.395(3) .
C5 C6 1.393(4) .
C5 C10 1.501(3) .
C6 N2 1.405(3) .
C6 C7 1.428(3) .
C7 C8 1.359(3) .
C7 H7 0.9300 .
C8 C9 1.416(3) .
C8 H8 0.9300 .
C9 N2 1.347(3) .
C9 C9 1.460(4) 3_576
C10 C11 1.374(3) .
C10 C15 1.379(4) .
C11 C12 1.404(3) .
C11 H11 0.9300 .
C12 C13 1.366(4) .
C12 H12 0.9300 .
C13 C14 1.377(4) .
C13 C16 1.498(3) .
C14 C15 1.383(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 O1 1.177(3) .
C16 O2 1.349(4) .
C17 O2 1.451(3) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 N3 1.319(3) .
C18 C19 1.403(4) .
C18 H18 0.9300 .
C19 C20 1.373(4) .
C19 H19 0.9300 .
C20 C21 1.421(3) .
C20 H20 0.9300 .
C21 C22 1.390(3) .
C21 N3 1.394(3) .
C22 C23 1.418(3) .
C22 C27 1.505(3) .
C23 N4 1.396(3) .
C23 C24 1.410(4) .
C24 C25 1.367(3) .
C24 H24 0.9300 .
C25 C26 1.402(3) .
C25 H25 0.9300 .
C26 N4 1.355(3) .
C26 C26 1.448(4) 4_656
C27 C32 1.376(3) .
C27 C28 1.384(4) .
C28 C29 1.390(4) .
C28 H28 0.9300 .
C29 C30 1.391(4) .
C29 H29 0.9300 .
C30 C31 1.363(4) .
C30 C33 1.498(3) .
C31 C32 1.381(4) .
C31 H31 0.9300 .
C32 H32 0.9300 .
C33 O3 1.196(4) .
C33 O4 1.326(4) .
C34 O4 1.446(4) .
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9600 .
N1 Zn1 1.9800(19) .
N2 Zn1 2.0056(19) .
N3 Zn1 1.987(2) .
N4 Zn1 2.0003(19) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.005 898 376 ' '
2 0.095 0.237 0.786 7 0 ' '
3 0.095 0.763 0.214 6 1 ' '
4 0.500 0.500 0.691 898 376 ' '
5 0.404 0.263 0.286 6 1 ' '
6 0.404 0.737 0.714 7 1 ' '
7 0.595 0.263 0.714 6 1 ' '
8 0.595 0.737 0.286 7 0 ' '
9 0.904 0.237 0.214 7 1 ' '
10 0.904 0.763 0.786 6 1 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139186064
