#------------------------------------------------------------------------------
#$Date: 2022-02-23 01:39:37 +0200 (Wed, 23 Feb 2022) $
#$Revision: 273118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244475.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_7244475
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            'C10 H10 Cu F N O4'
_chemical_formula_weight         290.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6004(3)
_cell_length_b                   14.1706(5)
_cell_length_c                   20.2294(8)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.85
_cell_measurement_theta_min      2.87
_cell_volume                     2178.75(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.960
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28014
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.507
_diffrn_reflns_theta_min         2.013
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.688
_exptl_transmission_factor_min   0.602
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0323
_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)+(0.1000P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             3486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01711j2.cif
_cod_data_source_block           1_a
_cod_database_code               7244475
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.53411(3) 0.39871(2) 0.48049(2) 0.02770(11) Uani 1 1 d . . . . .
O1 O 0.43291(16) 0.51576(8) 0.44362(5) 0.0244(2) Uani 1 1 d . . . . .
O2 O 0.6818(2) 0.28940(9) 0.50442(7) 0.0339(3) Uani 1 1 d . . . . .
O3 O 0.76647(19) 0.14922(9) 0.46633(9) 0.0403(3) Uani 1 1 d . . . . .
F1 F 0.3246(3) 0.73113(10) 0.27102(7) 0.0635(5) Uani 1 1 d . . . . .
N1 N 0.4907(2) 0.32789(11) 0.40123(8) 0.0277(3) Uani 1 1 d . . . . .
O4 O 0.7999(2) 0.47068(12) 0.41406(11) 0.0571(5) Uani 1 1 d . . . . .
H4 H 0.796100 0.523979 0.429776 0.086 Uiso 1 1 calc R U . . .
C6 C 0.3978(2) 0.45821(12) 0.33228(8) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.4414(2) 0.36129(13) 0.34581(9) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.432715 0.319065 0.310768 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4055(2) 0.53204(11) 0.37945(8) 0.0237(3) Uani 1 1 d . . . . .
C9 C 0.6765(2) 0.22168(12) 0.46335(9) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.3829(3) 0.62486(14) 0.35674(9) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.394714 0.675552 0.385605 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3538(3) 0.47945(15) 0.26619(9) 0.0375(4) Uani 1 1 d . . . . .
H4A H 0.346000 0.430381 0.235803 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3432(3) 0.63986(14) 0.29128(10) 0.0407(5) Uani 1 1 d . . . . .
C3 C 0.3222(3) 0.56951(18) 0.24523(9) 0.0440(5) Uani 1 1 d . . . . .
H3 H 0.288218 0.582518 0.202020 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5424(3) 0.22983(14) 0.40799(10) 0.0345(4) Uani 1 1 d . . . . .
H8A H 0.593058 0.207404 0.366887 0.041 Uiso 1 1 calc R U . . .
H8B H 0.440131 0.191441 0.418042 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9719(3) 0.4390(3) 0.41389(19) 0.0703(9) Uani 1 1 d . . . . .
H10A H 1.034006 0.466886 0.377467 0.105 Uiso 1 1 calc R U . . .
H10B H 0.973245 0.371571 0.409505 0.105 Uiso 1 1 calc R U . . .
H10C H 1.027967 0.456624 0.454595 0.105 Uiso 1 1 calc 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
N1 Cu1 O1 173.31(6) . 5_666 ?
N1 Cu1 O2 83.81(6) . . ?
O1 Cu1 O2 102.66(5) 5_666 . ?
N1 Cu1 O1 93.26(6) . . ?
O1 Cu1 O1 80.06(5) 5_666 . ?
O2 Cu1 O1 166.81(6) . . ?
N1 Cu1 O3 94.64(6) . 4_456 ?
O1 Cu1 O3 86.14(5) 5_666 4_456 ?
O2 Cu1 O3 98.63(6) . 4_456 ?
O1 Cu1 O3 94.41(5) . 4_456 ?
N1 Cu1 Cu1 133.25(5) . 5_666 ?
O1 Cu1 Cu1 40.06(3) 5_666 5_666 ?
O2 Cu1 Cu1 141.18(4) . 5_666 ?
O1 Cu1 Cu1 40.00(3) . 5_666 ?
O3 Cu1 Cu1 90.36(3) 4_456 5_666 ?
C5 O1 Cu1 132.13(10) . 5_666 ?
C5 O1 Cu1 124.98(10) . . ?
Cu1 O1 Cu1 99.94(5) 5_666 . ?
C9 O2 Cu1 114.49(11) . . ?
C9 O3 Cu1 136.60(13) . 4_556 ?
C7 N1 C8 121.26(15) . . ?
C7 N1 Cu1 126.26(13) . . ?
C8 N1 Cu1 112.06(12) . . ?
C10 O4 H4 109.5 . . ?
C4 C6 C5 119.36(16) . . ?
C4 C6 C7 116.00(16) . . ?
C5 C6 C7 124.55(15) . . ?
N1 C7 C6 126.16(16) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
O1 C5 C1 119.94(15) . . ?
O1 C5 C6 122.25(14) . . ?
C1 C5 C6 117.81(15) . . ?
O3 C9 O2 125.36(17) . . ?
O3 C9 C8 118.09(17) . . ?
O2 C9 C8 116.51(15) . . ?
C2 C1 C5 119.13(18) . . ?
C2 C1 H1 120.4 . . ?
C5 C1 H1 120.4 . . ?
C3 C4 C6 122.36(19) . . ?
C3 C4 H4A 118.8 . . ?
C6 C4 H4A 118.8 . . ?
F1 C2 C3 118.18(18) . . ?
F1 C2 C1 117.31(19) . . ?
C3 C2 C1 124.51(18) . . ?
C4 C3 C2 116.56(17) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
N1 C8 C9 108.90(14) . . ?
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 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 N1 1.9202(15) . ?
Cu1 O1 1.9720(11) 5_666 ?
Cu1 O2 1.9734(13) . ?
Cu1 O1 1.9746(12) . ?
Cu1 O3 2.3993(14) 4_456 ?
Cu1 Cu1 3.0220(4) 5_666 ?
O1 C5 1.3349(19) . ?
O2 C9 1.270(2) . ?
O3 C9 1.235(2) . ?
F1 C2 1.364(2) . ?
N1 C7 1.273(2) . ?
N1 C8 1.450(2) . ?
O4 C10 1.382(3) . ?
O4 H4 0.8200 . ?
C6 C4 1.411(2) . ?
C6 C5 1.417(2) . ?
C6 C7 1.439(3) . ?
C7 H7 0.9300 . ?
C5 C1 1.404(2) . ?
C9 C8 1.519(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C4 C3 1.366(3) . ?
C4 H4A 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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
C8 H8B O2 0.97 2.53 3.275(2) 133.8 4_456 yes
C1 H1 O2 0.93 2.35 3.099(2) 137.1 5_666 yes
C7 H7 F1 0.93 2.45 3.127(2) 129.3 8_655 yes
O4 H4 O3 0.82 1.98 2.788(2) 168.1 8_765 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
C8 N1 C7 C6 -175.92(17) . . . . ?
Cu1 N1 C7 C6 -4.0(3) . . . . ?
C4 C6 C7 N1 177.31(19) . . . . ?
C5 C6 C7 N1 0.7(3) . . . . ?
Cu1 O1 C5 C1 -4.7(2) 5_666 . . . ?
Cu1 O1 C5 C1 -161.20(12) . . . . ?
Cu1 O1 C5 C6 175.36(12) 5_666 . . . ?
Cu1 O1 C5 C6 18.9(2) . . . . ?
C4 C6 C5 O1 174.71(16) . . . . ?
C7 C6 C5 O1 -8.8(3) . . . . ?
C4 C6 C5 C1 -5.2(3) . . . . ?
C7 C6 C5 C1 171.25(17) . . . . ?
Cu1 O3 C9 O2 -19.9(3) 4_556 . . . ?
Cu1 O3 C9 C8 162.84(15) 4_556 . . . ?
Cu1 O2 C9 O3 175.22(16) . . . . ?
Cu1 O2 C9 C8 -7.5(2) . . . . ?
O1 C5 C1 C2 -175.71(17) . . . . ?
C6 C5 C1 C2 4.2(3) . . . . ?
C5 C6 C4 C3 1.7(3) . . . . ?
C7 C6 C4 C3 -175.1(2) . . . . ?
C5 C1 C2 F1 -179.18(18) . . . . ?
C5 C1 C2 C3 0.4(3) . . . . ?
C6 C4 C3 C2 2.9(3) . . . . ?
F1 C2 C3 C4 175.6(2) . . . . ?
C1 C2 C3 C4 -4.0(4) . . . . ?
C7 N1 C8 C9 150.95(17) . . . . ?
Cu1 N1 C8 C9 -22.02(19) . . . . ?
O3 C9 C8 N1 -163.03(17) . . . . ?
O2 C9 C8 N1 19.5(2) . . . . ?
