#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/94/1529412.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_1529412
loop_
_publ_author_name
'A.D. Vasilev'
'N.N. Golovnev'
'M.S. Molokeev'
'T.D. Churilov'
_publ_section_title
;
 Preparation and crystal structure of hydrated crystalline complex of
 ciprofloxacin and copper tetrachloride
;
_journal_issue                   2
_journal_name_full               'Journal of Structural Chemistry'
_journal_page_first              363
_journal_page_last               370
_journal_paper_doi               10.1007/s10947-006-0055-8
_journal_volume                  46
_journal_year                    2005
_chemical_formula_sum            'C17 H18 Cl4 Cu F N3 O4'
_chemical_formula_weight         552.68
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.392(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4910(10)
_cell_length_b                   11.0459(7)
_cell_length_c                   16.2990(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2261.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2388
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         50.00
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    6.050
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1116
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2280
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²+2.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                1902
_reflns_number_total             2280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cfH3CuCl4H2O.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1529412
_cod_database_fobs_code          1529412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.81558(4) 0.30657(5) 0.32603(4) 0.0388(3) Uani 1 1 d . . .
Cl1 Cl 0.68607(8) 0.17339(10) 0.26295(8) 0.0483(4) Uani 1 1 d . . .
Cl2 Cl 0.85436(9) 0.50432(9) 0.31399(9) 0.0549(4) Uani 1 1 d . . .
Cl3 Cl 0.93608(9) 0.24031(10) 0.26936(10) 0.0649(4) Uani 1 1 d . . .
Cl4 Cl 0.79877(11) 0.31562(15) 0.45580(8) 0.0787(5) Uani 1 1 d . . .
F F 0.42394(19) 0.4192(2) 0.51264(16) 0.0548(7) Uani 1 1 d . . .
O1 O 0.7220(2) 0.1266(4) 0.5952(2) 0.0639(10) Uani 1 1 d . . .
H1 H 0.7755 0.0840 0.6114 0.098(11) Uiso 1 1 calc R . .
O2 O 0.7952(3) -0.1501(3) 0.4519(2) 0.0669(10) Uani 1 1 d . . .
HO H 0.8536 -0.1828 0.4737 0.098(11) Uiso 1 1 calc R . .
O3 O 0.8524(3) -0.0404(4) 0.5766(3) 0.0829(12) Uani 1 1 d . . .
O4 O 0.9457(3) -0.2982(5) 0.4701(3) 0.0918(16) Uani 1 1 d D . .
HW1 H 1.010(4) -0.287(6) 0.486(4) 0.098(11) Uiso 1 1 d D . .
HW2 H 0.927(5) -0.347(5) 0.430(4) 0.098(11) Uiso 1 1 d D . .
N1 N 0.0756(2) 0.4670(3) 0.2725(2) 0.0373(9) Uani 1 1 d . . .
H1A H 0.0421 0.5350 0.2462 0.045(3) Uiso 1 1 calc R . .
H1B H 0.0257 0.4135 0.2734 0.045(3) Uiso 1 1 calc R . .
N2 N 0.2715(2) 0.3408(3) 0.3567(2) 0.0340(8) Uani 1 1 d . . .
N3 N 0.5137(2) 0.0188(3) 0.3544(2) 0.0329(8) Uani 1 1 d . . .
C1 C 0.2073(3) 0.3848(4) 0.4067(3) 0.0425(11) Uani 1 1 d . . .
H1A H 0.2536 0.4039 0.4665 0.045(3) Uiso 1 1 calc R . .
H1B H 0.1584 0.3219 0.4093 0.045(3) Uiso 1 1 calc R . .
C2 C 0.1460(3) 0.4952(4) 0.3639(3) 0.0447(12) Uani 1 1 d . . .
H2A H 0.1036 0.5231 0.3971 0.045(3) Uiso 1 1 calc R . .
H2B H 0.1949 0.5594 0.3636 0.045(3) Uiso 1 1 calc R . .
C3 C 0.1364(3) 0.4159(4) 0.2205(3) 0.0389(10) Uani 1 1 d . . .
H3A H 0.1823 0.4779 0.2115 0.045(3) Uiso 1 1 calc R . .
H3B H 0.0872 0.3906 0.1631 0.045(3) Uiso 1 1 calc R . .
C4 C 0.2025(3) 0.3100(4) 0.2666(3) 0.0370(10) Uani 1 1 d . . .
H4A H 0.1560 0.2437 0.2681 0.045(3) Uiso 1 1 calc R . .
H4B H 0.2459 0.2832 0.2340 0.045(3) Uiso 1 1 calc R . .
C5 C 0.5346(3) 0.2571(4) 0.5182(3) 0.0392(11) Uani 1 1 d . . .
H6 H 0.5816 0.2849 0.5723 0.045(3) Uiso 1 1 calc R . .
C6 C 0.4421(3) 0.3148(4) 0.4774(3) 0.0355(11) Uani 1 1 d . . .
C7 C 0.3630(3) 0.2753(3) 0.3964(2) 0.0305(10) Uani 1 1 d . . .
C8 C 0.3882(3) 0.1735(3) 0.3589(2) 0.0295(10) Uani 1 1 d . . .
H7 H 0.3385 0.1421 0.3073 0.045(3) Uiso 1 1 calc R . .
C9 C 0.4871(3) 0.1166(3) 0.3970(2) 0.0305(10) Uani 1 1 d . . .
C10 C 0.5601(3) 0.1542(4) 0.4788(3) 0.0324(10) Uani 1 1 d . . .
C11 C 0.6584(3) 0.0920(4) 0.5171(3) 0.0408(11) Uani 1 1 d . . .
C12 C 0.6822(3) -0.0031(4) 0.4711(3) 0.0392(11) Uani 1 1 d . . .
C13 C 0.6070(3) -0.0355(4) 0.3913(3) 0.0414(11) Uani 1 1 d . . .
H8 H 0.6226 -0.0998 0.3613 0.045(3) Uiso 1 1 calc R . .
C14 C 0.7857(4) -0.0657(5) 0.5057(4) 0.0590(14) Uani 1 1 d . . .
C15 C 0.4378(3) -0.0236(4) 0.2696(3) 0.0375(11) Uani 1 1 d . . .
H9 H 0.3769 -0.0695 0.2722 0.045(3) Uiso 1 1 calc R . .
C16 C 0.4769(4) -0.0598(5) 0.1993(3) 0.0533(13) Uani 1 1 d . . .
H10A H 0.4416 -0.1271 0.1616 0.045(3) Uiso 1 1 calc R . .
H10B H 0.5527 -0.0538 0.2117 0.045(3) Uiso 1 1 calc R . .
C17 C 0.4160(3) 0.0546(5) 0.1909(3) 0.0467(12) Uani 1 1 d . . .
H11A H 0.4549 0.1302 0.1982 0.045(3) Uiso 1 1 calc R . .
H11B H 0.3438 0.0570 0.1482 0.045(3) Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
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
Cl4 Cu Cl1 97.73(5) . .
Cl4 Cu Cl3 138.12(6) . .
Cl1 Cu Cl3 99.05(5) . .
Cl4 Cu Cl2 98.42(6) . .
Cl1 Cu Cl2 139.62(5) . .
Cl3 Cu Cl2 93.06(5) . .
C11 O1 H1 109.5 . .
C14 O2 HO 109.5 . .
HW1 O4 HW2 110(7) . .
C2 N1 C3 111.6(3) . .
C2 N1 H1A 109.3 . .
C3 N1 H1A 109.3 . .
C2 N1 H1B 109.3 . .
C3 N1 H1B 109.3 . .
H1A N1 H1B 108.0 . .
C7 N2 C4 118.9(3) . .
C7 N2 C1 121.6(3) . .
C4 N2 C1 110.2(3) . .
C13 N3 C9 119.8(3) . .
C13 N3 C15 120.4(3) . .
C9 N3 C15 119.8(3) . .
N2 C1 C2 110.4(3) . .
N2 C1 H1A 109.6 . .
C2 C1 H1A 109.6 . .
N2 C1 H1B 109.6 . .
C2 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
N1 C2 C1 109.9(3) . .
N1 C2 H2A 109.7 . .
C1 C2 H2A 109.7 . .
N1 C2 H2B 109.7 . .
C1 C2 H2B 109.7 . .
H2A C2 H2B 108.2 . .
N1 C3 C4 111.2(3) . .
N1 C3 H3A 109.4 . .
C4 C3 H3A 109.4 . .
N1 C3 H3B 109.4 . .
C4 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
N2 C4 C3 111.5(3) . .
N2 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
N2 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
C6 C5 C10 119.7(4) . .
C6 C5 H6 120.2 . .
C10 C5 H6 120.2 . .
C5 C6 F 118.4(4) . .
C5 C6 C7 124.0(4) . .
F C6 C7 117.6(4) . .
N2 C7 C8 123.1(4) . .
N2 C7 C6 121.0(4) . .
C8 C7 C6 115.8(4) . .
C7 C8 C9 121.2(4) . .
C7 C8 H7 119.4 . .
C9 C8 H7 119.4 . .
C8 C9 N3 120.1(3) . .
C8 C9 C10 121.0(4) . .
N3 C9 C10 118.9(3) . .
C9 C10 C5 118.0(3) . .
C9 C10 C11 119.6(4) . .
C5 C10 C11 122.3(4) . .
O1 C11 C12 123.1(4) . .
O1 C11 C10 117.6(4) . .
C12 C11 C10 119.3(4) . .
C13 C12 C11 118.0(4) . .
C13 C12 C14 120.7(4) . .
C11 C12 C14 121.3(4) . .
N3 C13 C12 124.4(4) . .
N3 C13 H8 117.8 . .
C12 C13 H8 117.8 . .
O3 C14 O2 125.5(4) . .
O3 C14 C12 121.9(5) . .
O2 C14 C12 112.7(5) . .
N3 C15 C16 119.6(3) . .
N3 C15 C17 118.7(3) . .
C16 C15 C17 60.1(3) . .
N3 C15 H9 115.7 . .
C16 C15 H9 115.7 . .
C17 C15 H9 115.7 . .
C15 C16 C17 60.1(3) . .
C15 C16 H10A 117.8 . .
C17 C16 H10A 117.8 . .
C15 C16 H10B 117.8 . .
C17 C16 H10B 117.8 . .
H10A C16 H10B 114.9 . .
C15 C17 C16 59.8(3) . .
C15 C17 H11A 117.8 . .
C16 C17 H11A 117.8 . .
C15 C17 H11B 117.8 . .
C16 C17 H11B 117.8 . .
H11A C17 H11B 114.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu Cl4 2.2102(14) .
Cu Cl1 2.2280(12) .
Cu Cl3 2.2642(12) .
Cu Cl2 2.2713(12) .
F C6 1.350(5) .
O1 C11 1.307(5) .
O1 H1 0.8200 .
O2 C14 1.318(6) .
O2 HO 0.8200 .
O3 C14 1.210(6) .
O4 HW1 0.82(4) .
O4 HW2 0.82(4) .
N1 C2 1.479(5) .
N1 C3 1.490(5) .
N1 H1A 0.9000 .
N1 H1B 0.9000 .
N2 C7 1.372(5) .
N2 C4 1.463(5) .
N2 C1 1.470(5) .
N3 C13 1.324(5) .
N3 C9 1.400(5) .
N3 C15 1.464(5) .
C1 C2 1.496(6) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.496(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.341(6) .
C5 C10 1.409(6) .
C5 H6 0.9300 .
C6 C7 1.431(6) .
C7 C8 1.381(5) .
C8 C9 1.399(5) .
C8 H7 0.9300 .
C9 C10 1.401(6) .
C10 C11 1.419(6) .
C11 C12 1.395(6) .
C12 C13 1.373(6) .
C12 C14 1.474(6) .
C13 H8 0.9300 .
C15 C16 1.481(6) .
C15 C17 1.485(6) .
C15 H9 0.9800 .
C16 C17 1.486(7) .
C16 H10A 0.9700 .
C16 H10B 0.9700 .
C17 H11A 0.9700 .
C17 H11B 0.9700 .
