#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:21:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179574 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/39/4503937.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_4503937
loop_
_publ_author_name
'Xiao, Dong-Rong'
'Wang, En-Bo'
'An, Hai-Yan'
'Li, Yang-Guang'
'Xu, Lin'
_publ_section_title
;
 Syntheses and Structures of Three Unprecedented
 Metal−Ciprofloxacin Complexes with Helical Character
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              506
_journal_paper_doi               10.1021/cg060492c
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C51 H50 F2 N6 O19 Zn2'
_chemical_formula_weight         1219.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.763(5)
_cell_length_b                   12.380(3)
_cell_length_c                   17.729(4)
_cell_measurement_reflns_used    21096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.15
_cell_volume                     4996(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21096
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.670
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                3793
_reflns_number_total             4873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060492csi20061127_055128.cif
_cod_data_source_block           dr61b
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4503937
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.212574(13) -0.09718(3) -0.20125(2) 0.03307(14) Uani 1 1 d . . .
F1 F 0.03797(8) 0.17138(16) -0.13769(14) 0.0514(5) Uani 1 1 d . . .
O1 O -0.14322(9) -0.3421(2) -0.03847(16) 0.0545(7) Uani 1 1 d . . .
OW1 O 0.4221(4) -0.0447(9) 0.6016(5) 0.155(4) Uani 0.60 1 d P . .
O2 O -0.19659(8) -0.2176(2) -0.12289(14) 0.0419(5) Uani 1 1 d . . .
O3 O -0.13182(8) -0.04207(18) -0.14817(13) 0.0360(5) Uani 1 1 d . . .
O4 O -0.28939(11) -0.0515(2) -0.19934(18) 0.0574(7) Uani 1 1 d . . .
O5 O -0.25043(11) 0.0827(3) -0.2376(2) 0.0706(9) Uani 1 1 d . . .
O6 O -0.25001(11) 0.2301(3) -0.09638(17) 0.0665(8) Uani 1 1 d . . .
O7 O -0.27412(9) 0.3640(2) -0.18572(13) 0.0398(5) Uani 1 1 d . . .
O8 O -0.5000 0.3773(2) -0.2500 0.0332(7) Uani 1 2 d S . .
N1 N 0.24873(12) 0.0634(3) -0.08266(19) 0.0531(8) Uani 1 1 d . . .
H1A H 0.2831 0.0968 -0.0730 0.064 Uiso 1 1 calc R . .
H1B H 0.2469 0.0039 -0.1128 0.064 Uiso 1 1 calc R . .
N2 N 0.13824(11) 0.0448(2) -0.06791(16) 0.0393(6) Uani 1 1 d . . .
C1 C -0.14736(12) -0.2585(3) -0.07901(18) 0.0349(7) Uani 1 1 d . . .
C2 C -0.09187(11) -0.2058(2) -0.07565(17) 0.0279(6) Uani 1 1 d . . .
C3 C -0.08858(11) -0.1034(2) -0.10870(16) 0.0262(6) Uani 1 1 d . . .
C4 C -0.03012(11) -0.0656(2) -0.09543(16) 0.0260(6) Uani 1 1 d . . .
C5 C -0.02251(12) 0.0363(2) -0.12367(17) 0.0293(6) Uani 1 1 d . . .
H5A H -0.0549 0.0807 -0.1496 0.035 Uiso 1 1 calc R . .
C6 C 0.03205(13) 0.0708(3) -0.11328(19) 0.0334(7) Uani 1 1 d . . .
C7 C 0.08278(11) 0.0073(3) -0.07596(18) 0.0315(6) Uani 1 1 d . . .
C8 C 0.07542(12) -0.0924(3) -0.04580(18) 0.0309(6) Uani 1 1 d . . .
H8A H 0.1081 -0.1356 -0.0188 0.037 Uiso 1 1 calc R . .
C9 C 0.01967(11) -0.1289(2) -0.05535(17) 0.0263(6) Uani 1 1 d . . .
C10 C -0.04142(11) -0.2640(3) -0.03738(18) 0.0320(6) Uani 1 1 d . . .
H10A H -0.0448 -0.3319 -0.0172 0.038 Uiso 1 1 calc R . .
N3 N 0.01266(9) -0.2302(2) -0.02673(14) 0.0306(5) Uani 1 1 d DU B .
C11 C 0.06253(13) -0.2998(3) 0.0116(2) 0.0494(9) Uani 1 1 d DU . .
H11A H 0.0800 -0.3214 -0.0270 0.049 Uiso 0.50 1 calc PR A 1
H11B H 0.0842 -0.2754 0.0681 0.049 Uiso 0.50 1 calc PR A 2
C12 C 0.1055(3) -0.2930(7) 0.0932(4) 0.058(2) Uani 0.50 1 d PDU B 1
H12A H 0.0995 -0.2399 0.1295 0.058 Uiso 0.50 1 calc PR B 1
H12B H 0.1462 -0.3052 0.1019 0.058 Uiso 0.50 1 calc PR B 1
C13 C 0.0640(3) -0.3879(6) 0.0672(5) 0.055(2) Uani 0.50 1 d PDU B 1
H13A H 0.0796 -0.4571 0.0595 0.055 Uiso 0.50 1 calc PR B 1
H13B H 0.0328 -0.3916 0.0872 0.055 Uiso 0.50 1 calc PR B 1
C12A C 0.1037(4) -0.3461(8) -0.0188(6) 0.073(2) Uani 0.50 1 d PDU B 2
H12C H 0.1452 -0.3424 0.0161 0.073 Uiso 0.50 1 calc PR B 2
H12D H 0.0943 -0.3419 -0.0772 0.073 Uiso 0.50 1 calc PR B 2
C13A C 0.0643(4) -0.4157(6) 0.0099(7) 0.073(3) Uani 0.50 1 d PDU B 2
H13C H 0.0316 -0.4530 -0.0316 0.073 Uiso 0.50 1 calc PR B 2
H13D H 0.0824 -0.4535 0.0617 0.073 Uiso 0.50 1 calc PR B 2
OW2 O 0.1762(4) -0.3603(9) -0.0216(6) 0.108(3) Uani 0.45 1 d P C 3
OW5 O 0.1466(6) -0.2391(14) 0.2019(9) 0.097(4) Uani 0.25 1 d PU D 3
C14 C 0.14164(15) 0.0806(3) -0.1457(2) 0.0444(8) Uani 1 1 d . . .
H14A H 0.1098 0.1304 -0.1738 0.053 Uiso 1 1 calc R . .
H14B H 0.1375 0.0187 -0.1811 0.053 Uiso 1 1 calc R . .
C15 C 0.20013(17) 0.1357(3) -0.1282(3) 0.0565(10) Uani 1 1 d . . .
H15A H 0.2027 0.1562 -0.1795 0.068 Uiso 1 1 calc R . .
H15B H 0.2029 0.2008 -0.0964 0.068 Uiso 1 1 calc R . .
C16 C 0.24575(16) 0.0320(5) -0.0039(2) 0.0692(14) Uani 1 1 d . . .
H16A H 0.2494 0.0958 0.0295 0.083 Uiso 1 1 calc R . .
H16B H 0.2781 -0.0161 0.0258 0.083 Uiso 1 1 calc R . .
C17 C 0.18809(12) -0.0240(3) -0.0189(2) 0.0479(9) Uani 1 1 d . . .
H17A H 0.1862 -0.0915 -0.0476 0.057 Uiso 1 1 calc R . .
H17B H 0.1858 -0.0404 0.0332 0.057 Uiso 1 1 calc R . .
C18 C -0.34448(12) 0.1098(2) -0.23343(18) 0.0312(6) Uani 1 1 d . . .
C19 C -0.34134(11) 0.2161(2) -0.20691(17) 0.0286(6) Uani 1 1 d . . .
C20 C -0.39276(11) 0.2699(2) -0.21509(17) 0.0282(6) Uani 1 1 d . . .
H20A H -0.3907 0.3413 -0.1977 0.034 Uiso 1 1 calc R . .
C21 C -0.44723(10) 0.2185(2) -0.24893(16) 0.0271(6) Uani 1 1 d . . .
C22 C -0.45009(12) 0.1150(2) -0.2796(2) 0.0338(7) Uani 1 1 d . . .
H22A H -0.4863 0.0815 -0.3057 0.041 Uiso 1 1 calc R . .
C23 C -0.39907(13) 0.0611(3) -0.27174(19) 0.0363(7) Uani 1 1 d . . .
H23A H -0.4014 -0.0085 -0.2924 0.044 Uiso 1 1 calc R . .
C24 C -0.29071(13) 0.0445(3) -0.22317(19) 0.0393(8) Uani 1 1 d . . .
C25 C -0.28336(12) 0.2717(3) -0.15982(19) 0.0352(7) Uani 1 1 d . . .
C26 C -0.5000 0.2797(3) -0.2500 0.0262(8) Uani 1 2 d S . .
OW3 O 0.5000 -0.1311(10) 0.7500 0.153(5) Uani 0.60 2 d SPU . .
OW4 O 0.3836(5) -0.1351(11) 0.6406(8) 0.125(4) Uani 0.40 1 d PU . .
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'
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
O7 Zn1 O3 107.71(9) 4_444 .
O7 Zn1 O2 116.27(10) 4_444 .
O3 Zn1 O2 92.36(9) . .
O7 Zn1 O4 108.02(11) 4_444 .
O3 Zn1 O4 133.58(11) . .
O2 Zn1 O4 97.49(10) . .
O7 Zn1 O5 93.56(11) 4_444 .
O3 Zn1 O5 91.29(10) . .
O2 Zn1 O5 147.08(10) . .
O4 Zn1 O5 57.92(10) . .
O7 Zn1 C24 101.71(10) 4_444 .
O3 Zn1 C24 113.94(10) . .
O2 Zn1 C24 124.28(10) . .
O4 Zn1 C24 29.43(11) . .
O5 Zn1 C24 28.50(10) . .
C1 O2 Zn1 127.90(18) . .
C3 O3 Zn1 122.18(19) . .
C24 O4 Zn1 99.2(2) . .
C24 O5 Zn1 81.3(2) . .
C25 O7 Zn1 127.0(2) . 4_454
C15 N1 C16 110.2(3) . .
C7 N2 C17 115.5(3) . .
C7 N2 C14 114.6(3) . .
C17 N2 C14 112.4(2) . .
O1 C1 O2 122.0(3) . .
O1 C1 C2 118.3(3) . .
O2 C1 C2 119.7(3) . .
C10 C2 C3 119.2(2) . .
C10 C2 C1 115.7(3) . .
C3 C2 C1 125.1(2) . .
O3 C3 C2 126.1(2) . .
O3 C3 C4 117.8(3) . .
C2 C3 C4 116.1(2) . .
C9 C4 C5 118.2(2) . .
C9 C4 C3 121.8(3) . .
C5 C4 C3 120.0(3) . .
C6 C5 C4 120.2(3) . .
F1 C6 C5 118.4(3) . .
F1 C6 C7 118.6(2) . .
C5 C6 C7 123.0(3) . .
C8 C7 N2 121.8(3) . .
C8 C7 C6 116.8(2) . .
N2 C7 C6 121.4(3) . .
C7 C8 C9 121.0(3) . .
N3 C9 C4 118.7(2) . .
N3 C9 C8 120.5(3) . .
C4 C9 C8 120.8(3) . .
N3 C10 C2 124.8(3) . .
C10 N3 C9 119.4(2) . .
C10 N3 C11 120.2(3) . .
C9 N3 C11 120.4(2) . .
C12 C11 C13A 93.7(6) . .
C12 C11 N3 127.2(4) . .
C13A C11 N3 128.1(5) . .
C12 C11 C12A 92.7(6) . .
C13A C11 C12A 64.2(4) . .
N3 C11 C12A 131.5(5) . .
C12 C11 C13 63.1(4) . .
C13A C11 C13 43.6(5) . .
N3 C11 C13 123.7(4) . .
C12A C11 C13 97.0(5) . .
C11 C12 C13 59.7(4) . .
C11 C13 C12 57.2(3) . .
C11 C12A C13A 57.6(4) . .
C11 C13A C12A 58.2(4) . .
N2 C14 C15 110.1(3) . .
N1 C15 C14 110.5(3) . .
N1 C16 C17 110.4(3) . .
N2 C17 C16 110.7(3) . .
C23 C18 C19 119.4(3) . .
C23 C18 C24 118.0(3) . .
C19 C18 C24 122.6(3) . .
C18 C19 C20 119.4(2) . .
C18 C19 C25 122.1(2) . .
C20 C19 C25 118.0(3) . .
C19 C20 C21 121.0(3) . .
C22 C21 C20 118.9(2) . .
C22 C21 C26 123.5(2) . .
C20 C21 C26 117.6(3) . .
C21 C22 C23 120.2(3) . .
C22 C23 C18 120.9(3) . .
O5 C24 O4 121.5(3) . .
O5 C24 C18 121.6(3) . .
O4 C24 C18 116.9(3) . .
O5 C24 Zn1 70.19(19) . .
O4 C24 Zn1 51.33(15) . .
C18 C24 Zn1 168.1(3) . .
O6 C25 O7 123.7(3) . .
O6 C25 C19 118.0(3) . .
O7 C25 C19 118.1(3) . .
O8 C26 C21 120.25(18) . 2_454
O8 C26 C21 120.25(18) . .
C21 C26 C21 119.5(4) 2_454 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O7 1.958(2) 4_444
Zn1 O3 1.967(2) .
Zn1 O2 1.969(2) .
Zn1 O4 1.998(2) .
Zn1 O5 2.403(3) .
Zn1 C24 2.525(3) .
F1 C6 1.345(4) .
O1 C1 1.241(4) .
OW1 OW4 1.776(17) .
O2 C1 1.265(4) .
O3 C3 1.273(3) .
O4 C24 1.257(5) .
O5 C24 1.219(4) .
O6 C25 1.216(4) .
O7 C25 1.286(4) .
O7 Zn1 1.958(2) 4_454
O8 C26 1.208(5) .
N1 C15 1.461(5) .
N1 C16 1.479(5) .
N2 C7 1.402(3) .
N2 C17 1.469(5) .
N2 C14 1.481(4) .
C1 C2 1.501(3) .
C2 C10 1.368(4) .
C2 C3 1.413(4) .
C3 C4 1.450(3) .
C4 C9 1.397(4) .
C4 C5 1.397(4) .
C5 C6 1.358(4) .
C6 C7 1.407(4) .
C7 C8 1.385(4) .
C8 C9 1.398(4) .
C9 N3 1.389(4) .
C10 N3 1.343(3) .
N3 C11 1.438(4) .
C11 C12 1.422(6) .
C11 C13A 1.435(7) .
C11 C12A 1.444(7) .
C11 C13 1.461(7) .
C12 C13 1.509(8) .
C12A C13A 1.529(8) .
C14 C15 1.518(4) .
C16 C17 1.513(4) .
C18 C23 1.389(4) .
C18 C19 1.389(4) .
C18 C24 1.507(4) .
C19 C20 1.393(4) .
C19 C25 1.512(4) .
C20 C21 1.396(4) .
C21 C22 1.382(4) .
C21 C26 1.504(3) .
C22 C23 1.386(4) .
C26 C21 1.504(3) 2_454
