#------------------------------------------------------------------------------
#$Date: 2022-02-23 01:39:37 +0200 (Wed, 23 Feb 2022) $
#$Revision: 273118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244477.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_7244477
loop_
_publ_author_name
'Li, Zhongkui'
'Su, Hao'
'Zhu, Yanhong'
'Yan, Li'
'Li, Hui'
_publ_section_title
;
 Structural transformation of copper coordination complexes accompanied
 with chiral transformation
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01711J
_journal_year                    2022
_chemical_formula_sum            'C18 H18 Cu2 F2 N2 O9'
_chemical_formula_weight         571.42
_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
_audit_update_record
;
2020-01-16 deposited with the CCDC.	2022-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.89(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.218(13)
_cell_length_b                   6.780(5)
_cell_length_c                   17.448(10)
_cell_measurement_reflns_used    1092
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.85
_cell_volume                     1903(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 0.977
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4203
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.530
_diffrn_reflns_theta_min         2.499
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_description       rodlike
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.630
_exptl_transmission_factor_min   0.498
_refine_diff_density_max         0.952
_refine_diff_density_min         -1.969
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0545
_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)+(0.1000P)²+0.7256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2643
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01711j2.cif
_cod_data_source_block           1_a_CCDC2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244477
_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   0.498
_shelx_estimated_absorpt_t_max   0.630
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
Cu1 Cu 0.37756(3) 0.40962(8) 0.29599(3) 0.0232(2) Uani 1 1 d . . . . .
F1 F 0.72576(17) 0.0796(5) 0.55626(19) 0.0434(8) Uani 1 1 d . . . . .
O1 O 0.49040(17) 0.3299(5) 0.35023(18) 0.0259(7) Uani 1 1 d . . . . .
O3 O 0.27224(18) 0.5508(5) 0.25430(19) 0.0285(7) Uani 1 1 d . . . . .
O4 O 0.1604(2) 0.6249(5) 0.2840(2) 0.0342(8) Uani 1 1 d . . . . .
N1 N 0.3481(2) 0.3647(5) 0.3910(2) 0.0216(7) Uani 1 1 d . . . . .
O5 O 1.000000 0.4107(8) 0.250000 0.0616(19) Uani 1 2 d S T P . .
H5C H 0.959150 0.488246 0.242520 0.074 Uiso 0.5 1 d R U P . .
H5D H 0.981010 0.294376 0.238570 0.074 Uiso 0.5 1 d R U P . .
C6 C 0.4843(2) 0.2680(6) 0.4845(2) 0.0209(8) Uani 1 1 d . . . . .
C3 C 0.5284(3) 0.2079(6) 0.5657(3) 0.0235(8) Uani 1 1 d . . . . .
H3 H 0.501348 0.209154 0.603297 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3975(2) 0.3189(6) 0.4633(3) 0.0229(8) Uani 1 1 d . . . . .
H7 H 0.375988 0.318468 0.505179 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2283(3) 0.5420(7) 0.2988(3) 0.0268(9) Uani 1 1 d . . . . .
C1 C 0.6468(2) 0.1466(6) 0.5338(3) 0.0262(9) Uani 1 1 d . . . . .
C5 C 0.5248(2) 0.2692(6) 0.4271(2) 0.0203(8) Uani 1 1 d . . . . .
C8 C 0.2615(2) 0.4140(6) 0.3760(3) 0.0241(9) Uani 1 1 d . . . . .
H8A H 0.257260 0.484978 0.422623 0.029 Uiso 1 1 calc R U . . .
H8B H 0.228735 0.294234 0.368560 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6077(3) 0.2060(6) 0.4541(3) 0.0279(9) Uani 1 1 d . . . . .
H4 H 0.636318 0.204327 0.417884 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6097(3) 0.1476(7) 0.5914(3) 0.0287(10) Uani 1 1 d . . . . .
H2 H 0.638319 0.109337 0.645352 0.034 Uiso 1 1 calc R U . . .
O2 O 0.4044(2) 0.5224(6) 0.2026(2) 0.0423(9) Uani 1 1 d . . . . .
H2B H 0.434944 0.442481 0.188496 0.051 Uiso 1 1 d R U . . .
H2C H 0.430804 0.630001 0.217266 0.051 Uiso 1 1 d R U . . .
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'
F F 0.0171 0.0103 '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'
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
O1 Cu1 N1 93.58(14) . . ?
O1 Cu1 O3 166.14(14) . . ?
N1 Cu1 O3 84.45(14) . . ?
O1 Cu1 O2 91.29(14) . . ?
N1 Cu1 O2 166.59(15) . . ?
O3 Cu1 O2 87.84(14) . . ?
O1 Cu1 O4 94.63(13) . 4_545 ?
N1 Cu1 O4 106.29(14) . 4_545 ?
O3 Cu1 O4 99.10(14) . 4_545 ?
O2 Cu1 O4 85.73(16) . 4_545 ?
C5 O1 Cu1 126.8(2) . . ?
C9 O3 Cu1 115.4(3) . . ?
C9 O4 Cu1 122.8(3) . 4 ?
C7 N1 C8 120.6(4) . . ?
C7 N1 Cu1 126.8(3) . . ?
C8 N1 Cu1 112.1(3) . . ?
H5C O5 H5D 108.0 . . ?
H5C O5 H5C 103.6 . 2_755 ?
H5D O5 H5C 146.9 . 2_755 ?
H5C O5 H5D 146.9 . 2_755 ?
H5D O5 H5D 43.7 . 2_755 ?
H5C O5 H5D 108.0 2_755 2_755 ?
C3 C6 C5 119.4(4) . . ?
C3 C6 C7 117.6(4) . . ?
C5 C6 C7 123.0(4) . . ?
C2 C3 C6 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C6 C3 H3 118.8 . . ?
N1 C7 C6 124.9(4) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
O4 C9 O3 125.3(4) . . ?
O4 C9 C8 117.9(4) . . ?
O3 C9 C8 116.8(4) . . ?
F1 C1 C2 118.2(4) . . ?
F1 C1 C4 118.2(4) . . ?
C2 C1 C4 123.6(4) . . ?
O1 C5 C4 118.1(4) . . ?
O1 C5 C6 124.4(3) . . ?
C4 C5 C6 117.5(4) . . ?
N1 C8 C9 108.9(3) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C1 C4 C5 120.3(4) . . ?
C1 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C1 C2 C3 116.8(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
Cu1 O2 H2B 109.8 . . ?
Cu1 O2 H2C 109.7 . . ?
H2B O2 H2C 108.3 . . ?
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 O1 1.911(3) . ?
Cu1 N1 1.923(4) . ?
Cu1 O3 1.948(3) . ?
Cu1 O2 1.998(4) . ?
Cu1 O4 2.335(4) 4_545 ?
F1 C1 1.352(5) . ?
O1 C5 1.324(5) . ?
O3 C9 1.263(6) . ?
O4 C9 1.239(5) . ?
N1 C7 1.283(5) . ?
N1 C8 1.459(5) . ?
O5 H5C 0.8500 . ?
O5 H5D 0.8500 . ?
O5 H5C 0.8500 2_755 ?
O5 H5D 0.8500 2_755 ?
C6 C3 1.408(5) . ?
C6 C5 1.410(6) . ?
C6 C7 1.448(5) . ?
C3 C2 1.372(6) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C9 C8 1.531(6) . ?
C1 C2 1.369(7) . ?
C1 C4 1.372(6) . ?
C5 C4 1.401(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
O2 H2B 0.8501 . ?
O2 H2C 0.8500 . ?
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
O5 H5C O4 0.85 2.15 2.987(5) 167.2 2_655 yes
O5 H5D O2 0.85 2.22 3.059(6) 167.4 3_545 yes
O5 H5D O2 0.85 2.63 3.059(6) 112.8 4_645 yes
C4 H4 O4 0.93 2.57 3.444(6) 156.4 3_545 yes
C2 H2 O3 0.93 2.64 3.471(5) 148.6 8_556 yes
O2 H2B O1 0.85 1.82 2.650(5) 165.1 2_655 yes
O2 H2C O5 0.85 2.21 3.059(6) 177.4 3_455 yes
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
C5 C6 C3 C2 -0.8(6) . . . . ?
C7 C6 C3 C2 176.9(4) . . . . ?
C8 N1 C7 C6 -179.9(4) . . . . ?
Cu1 N1 C7 C6 -8.2(6) . . . . ?
C3 C6 C7 N1 -175.6(4) . . . . ?
C5 C6 C7 N1 2.0(6) . . . . ?
Cu1 O4 C9 O3 -25.7(6) 4 . . . ?
Cu1 O4 C9 C8 155.9(3) 4 . . . ?
Cu1 O3 C9 O4 178.4(4) . . . . ?
Cu1 O3 C9 C8 -3.2(5) . . . . ?
Cu1 O1 C5 C4 176.3(3) . . . . ?
Cu1 O1 C5 C6 -5.2(6) . . . . ?
C3 C6 C5 O1 -177.3(4) . . . . ?
C7 C6 C5 O1 5.2(6) . . . . ?
C3 C6 C5 C4 1.1(6) . . . . ?
C7 C6 C5 C4 -176.4(4) . . . . ?
C7 N1 C8 C9 156.2(4) . . . . ?
Cu1 N1 C8 C9 -16.6(4) . . . . ?
O4 C9 C8 N1 -168.4(4) . . . . ?
O3 C9 C8 N1 13.1(5) . . . . ?
F1 C1 C4 C5 177.5(4) . . . . ?
C2 C1 C4 C5 -1.1(7) . . . . ?
O1 C5 C4 C1 178.3(4) . . . . ?
C6 C5 C4 C1 -0.2(6) . . . . ?
F1 C1 C2 C3 -177.1(4) . . . . ?
C4 C1 C2 C3 1.5(7) . . . . ?
C6 C3 C2 C1 -0.6(6) . . . . ?
