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#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/69/4516961.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_4516961
loop_
_publ_author_name
'Kundu, Arunangshu'
'Saikia, Swagata'
'Majumder, Manoj'
'Sengupta, Oindrila'
'Bhattacharya, Biswajit'
'De, Gobinda Chandra'
'Ghosh, Sushobhan'
_publ_section_title
;
 New Set of Multicomponent Crystals as Efficient Heterogeneous Catalysts
 for the Synthesis of Cyclic Carbonates.
;
_journal_issue                   3
_journal_name_full               'ACS omega'
_journal_page_first              5221
_journal_page_last               5232
_journal_paper_doi               10.1021/acsomega.9b00101
_journal_volume                  4
_journal_year                    2019
_chemical_formula_sum            'C42 H38 N2 O12 Zn2'
_chemical_formula_weight         893.48
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 116.769(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5019(11)
_cell_length_b                   10.4986(5)
_cell_length_c                   19.2899(11)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      2.2
_cell_volume                     3887.8(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.241
_diffrn_reflns_theta_min         2.211
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0390
_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)+(0.0536P)²+4.9507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3857
_reflns_number_total             5278
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b00101_si_001.cif
_cod_data_source_block           SG3
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516961
_shelx_shelxl_version_number     2018/3
_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.
;
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
Zn1 Zn 0.500000 0.74742(3) 0.750000 0.03515(10) Uani 1 2 d S T P
Zn2 Zn 0.500000 0.24606(3) 0.750000 0.03721(10) Uani 1 2 d S T P
O1 O 0.42403(8) 0.89194(16) 0.73837(10) 0.0493(4) Uani 1 1 d . . .
N1 N 0.50211(9) 0.74628(15) 0.85581(10) 0.0365(3) Uani 1 1 d . . .
O2 O 0.57733(9) 0.60321(17) 0.81170(10) 0.0525(4) Uani 1 1 d . . .
O6 O 0.44348(9) 0.10015(19) 0.67281(9) 0.0587(5) Uani 1 1 d . . .
O3 O 0.55734(9) 0.3902(2) 0.73043(10) 0.0603(5) Uani 1 1 d . . .
C6 C 0.64701(10) 0.3998(2) 0.69024(11) 0.0371(4) Uani 1 1 d . . .
C9 C 0.35482(10) 0.0919(2) 0.54186(11) 0.0381(4) Uani 1 1 d . . .
O5 O 0.41259(14) 0.2769(2) 0.60911(15) 0.0893(7) Uani 1 1 d . . .
C20 C 0.46218(11) 0.8285(2) 0.87090(12) 0.0426(5) Uani 1 1 d . . .
C16 C 0.54283(11) 0.6626(2) 0.90950(11) 0.0433(5) Uani 1 1 d . . .
O4 O 0.59321(15) 0.2132(2) 0.70453(17) 0.0965(8) Uani 1 1 d . . .
C7 C 0.59668(12) 0.3289(3) 0.70978(12) 0.0485(5) Uani 1 1 d . . .
C8 C 0.40615(11) 0.1621(2) 0.61178(12) 0.0459(5) Uani 1 1 d . . .
C1 C 0.64515(14) 0.5301(3) 0.68269(15) 0.0541(6) Uani 1 1 d . . .
H1 H 0.612321 0.576754 0.690958 0.065 Uiso 1 1 calc R U .
C10 C 0.35350(14) -0.0380(3) 0.53773(15) 0.0593(6) Uani 1 1 d . . .
H10 H 0.384471 -0.085155 0.580002 0.071 Uiso 1 1 calc R U .
C15 C 0.58652(14) 0.5767(2) 0.88776(13) 0.0555(6) Uani 1 1 d . . .
H15A H 0.635170 0.587640 0.924381 0.067 Uiso 1 1 calc R U .
H15B H 0.573911 0.488771 0.890548 0.067 Uiso 1 1 calc R U .
C5 C 0.69587(13) 0.3321(3) 0.67744(16) 0.0573(6) Uani 1 1 d . . .
H5 H 0.697867 0.243886 0.682185 0.069 Uiso 1 1 calc R U .
C21 C 0.41822(13) 0.9174(2) 0.80748(15) 0.0538(6) Uani 1 1 d . . .
H21A H 0.369958 0.908652 0.797353 0.065 Uiso 1 1 calc R U .
H21B H 0.432572 1.004346 0.823786 0.065 Uiso 1 1 calc R U .
C14 C 0.30817(14) 0.1608(3) 0.47897(14) 0.0594(6) Uani 1 1 d . . .
H14 H 0.308419 0.249271 0.481018 0.071 Uiso 1 1 calc R U .
C19 C 0.46208(15) 0.8280(3) 0.94260(16) 0.0702(8) Uani 1 1 d . . .
H19 H 0.434182 0.884801 0.953017 0.084 Uiso 1 1 calc R U .
C17 C 0.54445(16) 0.6582(3) 0.98180(14) 0.0698(8) Uani 1 1 d . . .
H17 H 0.572504 0.599529 1.018790 0.084 Uiso 1 1 calc R U .
C4 C 0.74198(15) 0.3958(4) 0.65750(19) 0.0749(9) Uani 1 1 d . . .
H4 H 0.774954 0.349974 0.649029 0.090 Uiso 1 1 calc R U .
C3 C 0.73934(17) 0.5243(4) 0.6503(2) 0.0811(10) Uani 1 1 d . . .
H3 H 0.770249 0.566407 0.636596 0.097 Uiso 1 1 calc R U .
C12 C 0.26058(16) -0.0311(4) 0.40913(18) 0.0824(10) Uani 1 1 d . . .
H12 H 0.229189 -0.072836 0.364512 0.099 Uiso 1 1 calc R U .
C13 C 0.26082(15) 0.0984(4) 0.41262(16) 0.0770(9) Uani 1 1 d . . .
H13 H 0.229241 0.145185 0.370533 0.092 Uiso 1 1 calc R U .
C2 C 0.69104(18) 0.5921(3) 0.6632(2) 0.0783(9) Uani 1 1 d . . .
H2 H 0.689450 0.680362 0.658612 0.094 Uiso 1 1 calc R U .
C11 C 0.30690(18) -0.1001(3) 0.47179(19) 0.0847(10) Uani 1 1 d . . .
H11 H 0.306767 -0.188588 0.469642 0.102 Uiso 1 1 calc R U .
C18 C 0.50356(17) 0.7428(4) 0.99815(15) 0.0874(15) Uani 1 1 d . . .
H18 H 0.504161 0.741943 1.046659 0.105 Uiso 1 1 calc R U .
H2A H 0.5737(18) 0.526(3) 0.784(2) 0.071(10) Uiso 1 1 d . . .
H1A H 0.426(2) 0.973(3) 0.713(2) 0.087(11) Uiso 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_1
_geom_angle_site_symmetry_3
N1 Zn1 N1 179.32(9) 2_656 .
N1 Zn1 O1 103.10(6) 2_656 .
N1 Zn1 O1 77.38(7) . .
N1 Zn1 O1 77.38(7) 2_656 2_656
N1 Zn1 O1 103.11(6) . 2_656
O1 Zn1 O1 91.06(9) . 2_656
N1 Zn1 O2 77.20(7) 2_656 2_656
N1 Zn1 O2 102.31(7) . 2_656
O1 Zn1 O2 94.37(7) . 2_656
O1 Zn1 O2 154.58(7) 2_656 2_656
N1 Zn1 O2 102.31(6) 2_656 .
N1 Zn1 O2 77.20(7) . .
O1 Zn1 O2 154.58(7) . .
O1 Zn1 O2 94.37(7) 2_656 .
O2 Zn1 O2 91.30(10) 2_656 .
O3 Zn2 O3 87.26(10) . 2_656
O3 Zn2 O6 126.86(6) . .
O3 Zn2 O6 117.13(8) 2_656 .
O3 Zn2 O6 117.13(7) . 2_656
O3 Zn2 O6 126.86(6) 2_656 2_656
O6 Zn2 O6 86.33(10) . 2_656
C21 O1 Zn1 114.57(14) . .
C21 O1 H1A 110(2) . .
Zn1 O1 H1A 117(2) . .
C20 N1 C16 120.98(18) . .
C20 N1 Zn1 119.40(14) . .
C16 N1 Zn1 119.61(14) . .
C15 O2 Zn1 114.90(14) . .
C15 O2 H2A 110(2) . .
Zn1 O2 H2A 116(2) . .
C8 O6 Zn2 101.95(16) . .
C7 O3 Zn2 102.80(17) . .
C1 C6 C5 118.8(2) . .
C1 C6 C7 122.2(2) . .
C5 C6 C7 119.0(2) . .
C10 C9 C14 118.9(2) . .
C10 C9 C8 122.1(2) . .
C14 C9 C8 118.9(2) . .
N1 C20 C19 120.3(2) . .
N1 C20 C21 117.21(18) . .
C19 C20 C21 122.5(2) . .
N1 C16 C17 120.9(2) . .
N1 C16 C15 117.02(18) . .
C17 C16 C15 122.1(2) . .
O4 C7 O3 120.6(2) . .
O4 C7 C6 120.0(2) . .
O3 C7 C6 119.4(2) . .
O5 C8 O6 120.8(2) . .
O5 C8 C9 120.1(2) . .
O6 C8 C9 119.2(2) . .
C2 C1 C6 120.8(3) . .
C2 C1 H1 119.6 . .
C6 C1 H1 119.6 . .
C9 C10 C11 120.9(3) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
O2 C15 C16 111.11(18) . .
O2 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
O2 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C6 C5 C4 119.9(3) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
O1 C21 C20 111.22(18) . .
O1 C21 H21A 109.4 . .
C20 C21 H21A 109.4 . .
O1 C21 H21B 109.4 . .
C20 C21 H21B 109.4 . .
H21A C21 H21B 108.0 . .
C9 C14 C13 120.3(3) . .
C9 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C18 C19 C20 119.3(3) . .
C18 C19 H19 120.3 . .
C20 C19 H19 120.3 . .
C16 C17 C18 118.7(3) . .
C16 C17 H17 120.7 . .
C18 C17 H17 120.7 . .
C3 C4 C5 120.4(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C4 C3 C2 119.9(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C13 C12 C11 119.8(3) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C12 C13 C14 120.1(3) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C1 C2 C3 120.1(3) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C12 C11 C10 120.0(3) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C19 C18 C17 119.8(2) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.0212(16) 2_656
Zn1 N1 2.0212(16) .
Zn1 O1 2.1658(16) .
Zn1 O1 2.1658(16) 2_656
Zn1 O2 2.1659(17) 2_656
Zn1 O2 2.1659(16) .
Zn2 O3 2.0909(18) .
Zn2 O3 2.0909(18) 2_656
Zn2 O6 2.1001(18) .
Zn2 O6 2.1001(18) 2_656
O1 C21 1.419(3) .
O1 H1A 0.99(4) .
N1 C20 1.338(3) .
N1 C16 1.339(3) .
O2 C15 1.417(3) .
O2 H2A 0.95(3) .
O6 C8 1.266(3) .
O3 C7 1.262(3) .
C6 C1 1.375(3) .
C6 C5 1.379(3) .
C6 C7 1.495(3) .
C9 C10 1.366(3) .
C9 C14 1.380(3) .
C9 C8 1.496(3) .
O5 C8 1.218(3) .
C20 C19 1.384(3) .
C20 C21 1.490(3) .
C16 C17 1.380(3) .
C16 C15 1.492(3) .
O4 C7 1.219(3) .
C1 C2 1.369(4) .
C1 H1 0.9300 .
C10 C11 1.378(4) .
C10 H10 0.9300 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C5 C4 1.386(4) .
C5 H5 0.9300 .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C14 C13 1.389(4) .
C14 H14 0.9300 .
C19 C18 1.372(4) .
C19 H19 0.9300 .
C17 C18 1.382(4) .
C17 H17 0.9300 .
C4 C3 1.355(5) .
C4 H4 0.9300 .
C3 C2 1.371(5) .
C3 H3 0.9300 .
C12 C13 1.361(5) .
C12 C11 1.376(5) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C2 H2 0.9300 .
C11 H11 0.9300 .
C18 H18 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C21 H21B O4 0.97 2.27 3.116(3) 145.6 2_666 yes
O2 H2A O3 0.95(3) 1.70(3) 2.652(3) 174(3) . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346350
