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#$Date: 2022-03-17 01:45:57 +0200 (Thu, 17 Mar 2022) $
#$Revision: 273746 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244618.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_7244618
loop_
_publ_author_name
'Si, Chang-Dai'
'Zhang, Jianbin'
'Pan, Feng-Feng'
'Wang, Peng'
'Liao, Tian-Lu'
'Zheng, Wan-He'
'Yuan, Kun'
'Liu, Jia-Cheng'
_publ_section_title
;
 Zn/Cu Complexes Constructed through Selective in Situ Br−Cl
 Exchange: Synthesis, Structures, Properties, and DFT Insights into the
 Cu-Catalyzed Mechanism
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00128D
_journal_year                    2022
_chemical_formula_sum            'C15 H7 Cl Cu2 O9'
_chemical_formula_weight         493.74
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-22 deposited with the CCDC.	2022-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                69.6840(10)
_cell_angle_beta                 87.1130(10)
_cell_angle_gamma                76.2100(10)
_cell_formula_units_Z            2
_cell_length_a                   8.04580(10)
_cell_length_b                   10.7531(2)
_cell_length_c                   11.7107(2)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.93
_cell_volume                     922.18(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24203
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    2.496
_exptl_crystal_colour            BLUE
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_description       LUMP
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      13.334
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0494P)²+0.5028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2880
_reflns_number_total             3255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00128d2.cif
_cod_data_source_block           shelx
_cod_database_code               7244618
_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.
;
_shelx_estimated_absorpt_t_min   0.635
_shelx_estimated_absorpt_t_max   0.706
_platon_squeeze_void_probe_radius 1.20
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
Cu1 Cu -0.01562(4) 1.12209(3) 0.04654(3) 0.02136(12) Uani 1 1 d . . . . .
Cu2 Cu 0.64606(4) 1.09211(3) 0.89532(3) 0.02352(12) Uani 1 1 d . . . . .
Cl1 Cl -0.31587(11) 0.86800(12) 0.50372(9) 0.0554(3) Uani 1 1 d . . . . .
O1 O -0.1890(3) 0.9188(3) 0.2591(2) 0.0478(7) Uani 1 1 d D . . . .
O2 O 0.0522(3) 0.9867(2) 0.21543(18) 0.0296(5) Uani 1 1 d . . . . .
O3 O 0.5948(2) 0.9163(2) 0.9259(2) 0.0299(5) Uani 1 1 d . . . . .
O4 O 0.8539(2) 0.7780(2) 0.9296(2) 0.0295(5) Uani 1 1 d D . . . .
O5 O 0.6376(3) 0.2814(2) 0.8552(2) 0.0396(6) Uani 1 1 d . . . . .
O6 O 0.8646(3) 0.3065(2) 0.9399(2) 0.0352(5) Uani 1 1 d D . . . .
O8 O -0.1761(2) 1.02720(18) 0.01750(17) 0.0194(4) Uani 1 1 d . . . . .
H8 H -0.210108 0.981726 0.082111 0.023 Uiso 1 1 calc R U . . .
O9 O 0.4825(3) 1.1616(2) 0.7534(2) 0.0433(6) Uani 1 1 d D . . . .
O10 O 0.1950(2) 0.7091(2) 0.78145(18) 0.0280(5) Uani 1 1 d . . . . .
C1 C -0.0489(4) 0.9284(3) 0.2894(3) 0.0270(6) Uani 1 1 d . . . . .
C2 C 0.0114(4) 0.8672(3) 0.4208(3) 0.0272(6) Uani 1 1 d . . . . .
C3 C -0.0946(4) 0.8365(3) 0.5199(3) 0.0272(6) Uani 1 1 d . . . . .
C4 C -0.0296(4) 0.7832(3) 0.6385(3) 0.0279(7) Uani 1 1 d . . . . .
H4 H -0.102567 0.763689 0.703084 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1449(4) 0.7588(3) 0.6607(3) 0.0240(6) Uani 1 1 d . . . . .
C6 C 0.2536(4) 0.7876(4) 0.5653(3) 0.0346(7) Uani 1 1 d . . . . .
H6 H 0.370973 0.770250 0.579713 0.042 Uiso 1 1 calc R U . . .
C7 C 0.1848(4) 0.8426(3) 0.4483(3) 0.0355(8) Uani 1 1 d . . . . .
H7 H 0.258120 0.864559 0.384305 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3709(3) 0.6694(3) 0.8121(3) 0.0232(6) Uani 1 1 d . . . . .
C9 C 0.4597(4) 0.5401(3) 0.8234(3) 0.0253(6) Uani 1 1 d . . . . .
H9 H 0.407202 0.482859 0.801680 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6295(4) 0.4941(3) 0.8677(3) 0.0238(6) Uani 1 1 d . . . . .
C11 C 0.7072(4) 0.5813(3) 0.8981(3) 0.0226(6) Uani 1 1 d . . . . .
H11 H 0.820418 0.551701 0.927255 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6151(3) 0.7132(3) 0.8847(3) 0.0208(6) Uani 1 1 d . . . . .
C13 C 0.4454(4) 0.7577(3) 0.8407(3) 0.0228(6) Uani 1 1 d . . . . .
H13 H 0.383649 0.845874 0.830917 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6951(3) 0.8098(3) 0.9166(3) 0.0210(6) Uani 1 1 d . . . . .
C15 C 0.7198(4) 0.3485(3) 0.8891(3) 0.0244(6) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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
O8 Cu1 O4 178.16(9) . 2_676 ?
O8 Cu1 O6 96.38(8) . 1_464 ?
O4 Cu1 O6 82.17(8) 2_676 1_464 ?
O8 Cu1 O2 93.57(8) . . ?
O4 Cu1 O2 88.25(9) 2_676 . ?
O6 Cu1 O2 149.33(10) 1_464 . ?
O8 Cu1 O8 83.43(7) . 2_575 ?
O4 Cu1 O8 96.43(8) 2_676 2_575 ?
O6 Cu1 O8 124.47(9) 1_464 2_575 ?
O2 Cu1 O8 85.42(8) . 2_575 ?
O8 Cu2 O5 96.29(9) 1_656 1_565 ?
O8 Cu2 O3 95.66(8) 1_656 . ?
O5 Cu2 O3 165.87(9) 1_565 . ?
O8 Cu2 O9 173.12(10) 1_656 . ?
O5 Cu2 O9 82.73(9) 1_565 . ?
O3 Cu2 O9 86.29(9) . . ?
C1 O2 Cu1 124.87(19) . . ?
C14 O3 Cu2 127.19(19) . . ?
C14 O4 Cu1 131.33(18) . 2_676 ?
C15 O5 Cu2 135.1(2) . 1_545 ?
C15 O6 Cu1 130.68(19) . 1_646 ?
Cu2 O8 Cu1 128.66(10) 1_454 . ?
Cu2 O8 Cu1 102.03(8) 1_454 2_575 ?
Cu1 O8 Cu1 96.57(7) . 2_575 ?
Cu2 O8 H8 109.5 1_454 . ?
Cu1 O8 H8 110.6 . . ?
Cu1 O8 H8 105.9 2_575 . ?
C5 O10 C8 118.5(2) . . ?
O1 C1 O2 124.0(3) . . ?
O1 C1 C2 120.1(3) . . ?
O2 C1 C2 115.9(3) . . ?
C7 C2 C3 116.3(3) . . ?
C7 C2 C1 118.6(3) . . ?
C3 C2 C1 125.1(3) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 Cl1 115.4(2) . . ?
C2 C3 Cl1 122.9(2) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
O10 C5 C6 124.7(3) . . ?
O10 C5 C4 114.9(3) . . ?
C6 C5 C4 120.4(3) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 123.4(3) . . ?
C6 C7 H7 118.3 . . ?
C2 C7 H7 118.3 . . ?
C9 C8 C13 121.7(3) . . ?
C9 C8 O10 119.3(3) . . ?
C13 C8 O10 118.7(3) . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 C15 121.4(3) . . ?
C9 C10 C15 118.9(3) . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 C14 121.1(2) . . ?
C13 C12 C14 118.8(2) . . ?
C8 C13 C12 119.1(3) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
O4 C14 O3 126.7(3) . . ?
O4 C14 C12 116.4(2) . . ?
O3 C14 C12 116.9(2) . . ?
O6 C15 O5 127.1(3) . . ?
O6 C15 C10 117.6(3) . . ?
O5 C15 C10 115.3(3) . . ?
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
Cu1 O8 1.9333(18) . ?
Cu1 O4 1.9595(19) 2_676 ?
Cu1 O6 1.978(2) 1_464 ?
Cu1 O2 2.015(2) . ?
Cu1 O8 2.2490(18) 2_575 ?
Cu2 O8 1.9021(18) 1_656 ?
Cu2 O5 1.908(2) 1_565 ?
Cu2 O3 1.939(2) . ?
Cu2 O9 1.985(2) . ?
Cl1 C3 1.739(3) . ?
O1 C1 1.236(4) . ?
O2 C1 1.265(4) . ?
O3 C14 1.270(3) . ?
O4 C14 1.244(3) . ?
O5 C15 1.253(4) . ?
O6 C15 1.244(4) . ?
O8 H8 0.8200 . ?
O10 C5 1.370(3) . ?
O10 C8 1.404(3) . ?
C1 C2 1.502(4) . ?
C2 C7 1.389(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C6 C7 1.375(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.367(4) . ?
C8 C13 1.373(4) . ?
C9 C10 1.397(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 C15 1.498(4) . ?
C11 C12 1.394(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(4) . ?
C12 C14 1.498(4) . ?
C13 H13 0.9300 . ?
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
Cu1 O2 C1 O1 19.3(4) . . . . ?
Cu1 O2 C1 C2 -161.39(19) . . . . ?
O1 C1 C2 C7 160.9(3) . . . . ?
O2 C1 C2 C7 -18.4(4) . . . . ?
O1 C1 C2 C3 -21.4(5) . . . . ?
O2 C1 C2 C3 159.3(3) . . . . ?
C7 C2 C3 C4 -0.8(5) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
C7 C2 C3 Cl1 176.8(3) . . . . ?
C1 C2 C3 Cl1 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
Cl1 C3 C4 C5 -177.9(2) . . . . ?
C8 O10 C5 C6 -7.7(4) . . . . ?
C8 O10 C5 C4 174.0(3) . . . . ?
C3 C4 C5 O10 178.4(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
O10 C5 C6 C7 -177.3(3) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 C2 -2.0(5) . . . . ?
C3 C2 C7 C6 1.9(5) . . . . ?
C1 C2 C7 C6 179.7(3) . . . . ?
C5 O10 C8 C9 -86.1(3) . . . . ?
C5 O10 C8 C13 99.7(3) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
O10 C8 C9 C10 -172.5(3) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 C15 175.0(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C15 C10 C11 C12 -175.5(3) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C10 C11 C12 C14 -180.0(3) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
O10 C8 C13 C12 172.7(2) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C14 C12 C13 C8 -179.6(3) . . . . ?
Cu1 O4 C14 O3 -6.3(5) 2_676 . . . ?
Cu1 O4 C14 C12 172.63(19) 2_676 . . . ?
Cu2 O3 C14 O4 28.0(4) . . . . ?
Cu2 O3 C14 C12 -151.0(2) . . . . ?
C11 C12 C14 O4 15.0(4) . . . . ?
C13 C12 C14 O4 -164.8(3) . . . . ?
C11 C12 C14 O3 -165.9(3) . . . . ?
C13 C12 C14 O3 14.3(4) . . . . ?
Cu1 O6 C15 O5 -28.3(5) 1_646 . . . ?
Cu1 O6 C15 C10 150.1(2) 1_646 . . . ?
Cu2 O5 C15 O6 20.1(5) 1_545 . . . ?
Cu2 O5 C15 C10 -158.4(2) 1_545 . . . ?
C11 C10 C15 O6 2.9(4) . . . . ?
C9 C10 C15 O6 -172.9(3) . . . . ?
C11 C10 C15 O5 -178.4(3) . . . . ?
C9 C10 C15 O5 5.7(4) . . . . ?
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 -0.034 0.500 0.500 185 47 ' '
