#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:21:30 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179574 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/39/4503935.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_4503935
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            'C26 H24 F N3 O10 Zn'
_chemical_formula_weight         622.85
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.954(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4906(13)
_cell_length_b                   12.3673(13)
_cell_length_c                   16.6196(17)
_cell_measurement_reflns_used    15111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.88
_cell_volume                     2520.5(5)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_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 0.01
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       ω-2θ
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15111
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.637
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                4326
_reflns_number_total             5865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060492csi20060726_063142.cif
_cod_data_source_block           dr71b
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4503935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Zn1 Zn 0.668505(16) 0.021765(17) -0.211022(14) 0.03098(8) Uani 1 1 d .
F1 F 0.17199(8) 0.08969(9) -0.11101(7) 0.0431(3) Uani 1 1 d .
O1 O 0.76907(10) -0.23468(12) -0.06278(10) 0.0508(4) Uani 1 1 d .
OW1 O 0.2291(6) -0.4789(5) 0.0431(4) 0.114(2) Uani 0.50 1 d P
O2 O 0.74444(9) -0.09753(11) -0.14881(8) 0.0373(3) Uani 1 1 d .
O3 O 0.55166(10) 0.02400(9) -0.14382(8) 0.0319(3) Uani 1 1 d .
O4 O 0.82188(11) 0.03578(11) -0.28164(9) 0.0434(4) Uani 1 1 d .
O5 O 0.75751(10) 0.15486(10) -0.20417(8) 0.0365(3) Uani 1 1 d .
O6 O 0.93617(10) 0.52654(10) -0.18234(8) 0.0336(3) Uani 1 1 d .
O7 O 1.11283(10) 0.51209(10) -0.13171(9) 0.0394(3) Uani 1 1 d .
O8 O 1.29956(11) 0.22187(12) -0.27010(11) 0.0566(4) Uani 1 1 d .
O9 O 1.19960(11) 0.08572(12) -0.33025(10) 0.0504(4) Uani 1 1 d .
H9A H 1.269(2) 0.063(2) -0.3406(15) 0.069(8) Uiso 1 1 d .
N1 N -0.03780(12) -0.26736(13) -0.10557(10) 0.0363(4) Uani 1 1 d .
H1A H -0.1023 -0.2530 -0.0912 0.044 Uiso 1 1 calc R
H1B H -0.0448 -0.3297 -0.1341 0.044 Uiso 1 1 calc R
N2 N 0.10028(11) -0.08956(12) -0.03860(9) 0.0278(3) Uani 1 1 d .
N3 N 0.46940(11) -0.23221(11) -0.01081(9) 0.0274(3) Uani 1 1 d .
C1 C 0.71206(13) -0.16012(15) -0.09759(11) 0.0305(4) Uani 1 1 d .
C2 C 0.60035(13) -0.14671(14) -0.07844(11) 0.0263(4) Uani 1 1 d .
C3 C 0.52897(13) -0.05804(13) -0.10410(10) 0.0237(4) Uani 1 1 d .
C4 C 0.42240(13) -0.06448(14) -0.08240(10) 0.0236(4) Uani 1 1 d .
C5 C 0.34423(14) 0.01594(14) -0.10765(11) 0.0271(4) Uani 1 1 d .
H5A H 0.3620 0.0760 -0.1362 0.033 Uiso 1 1 calc R
C6 C 0.24276(14) 0.00641(14) -0.09059(12) 0.0283(4) Uani 1 1 d .
C7 C 0.20768(13) -0.08399(14) -0.05055(10) 0.0254(4) Uani 1 1 d .
C8 C 0.28654(13) -0.16081(14) -0.02167(10) 0.0263(4) Uani 1 1 d .
H8A H 0.2688 -0.2192 0.0086 0.032 Uiso 1 1 calc R
C9 C 0.39228(13) -0.15195(14) -0.03724(10) 0.0245(4) Uani 1 1 d .
C10 C 0.56652(13) -0.22812(14) -0.03350(11) 0.0293(4) Uani 1 1 d .
H10A H 0.6147 -0.2849 -0.0175 0.035 Uiso 1 1 calc R
C11 C 0.44173(15) -0.32531(15) 0.03514(12) 0.0361(4) Uani 1 1 d .
H11A H 0.3923 -0.3782 0.0036 0.043 Uiso 1 1 calc R
C12 C 0.42938(19) -0.3095(2) 0.12149(13) 0.0515(6) Uani 1 1 d .
H12A H 0.3730 -0.3504 0.1408 0.062 Uiso 1 1 calc R
H12B H 0.4423 -0.2377 0.1448 0.062 Uiso 1 1 calc R
C13 C 0.52398(19) -0.3698(2) 0.10242(15) 0.0607(7) Uani 1 1 d .
H13A H 0.5948 -0.3348 0.1143 0.073 Uiso 1 1 calc R
H13B H 0.5255 -0.4475 0.1103 0.073 Uiso 1 1 calc R
C14 C 0.01192(14) -0.07475(16) -0.11044(12) 0.0334(4) Uani 1 1 d .
H14A H 0.0325 -0.0187 -0.1454 0.040 Uiso 1 1 calc R
H14B H -0.0537 -0.0513 -0.0923 0.040 Uiso 1 1 calc R
C15 C -0.01135(15) -0.17879(17) -0.15912(12) 0.0388(5) Uani 1 1 d .
H15A H -0.0722 -0.1678 -0.2042 0.047 Uiso 1 1 calc R
H15B H 0.0519 -0.1987 -0.1818 0.047 Uiso 1 1 calc R
C16 C 0.04641(15) -0.28142(15) -0.03036(13) 0.0364(4) Uani 1 1 d .
H16A H 0.1127 -0.3094 -0.0449 0.044 Uiso 1 1 calc R
H16B H 0.0211 -0.3334 0.0055 0.044 Uiso 1 1 calc R
C17 C 0.07031(14) -0.17502(14) 0.01401(11) 0.0302(4) Uani 1 1 d .
H17A H 0.0064 -0.1524 0.0349 0.036 Uiso 1 1 calc R
H17B H 0.1294 -0.1851 0.0605 0.036 Uiso 1 1 calc R
C18 C 0.92728(13) 0.19402(13) -0.24233(10) 0.0241(4) Uani 1 1 d .
C19 C 0.93049(13) 0.29745(13) -0.20894(10) 0.0248(4) Uani 1 1 d .
H19A H 0.8698 0.3242 -0.1906 0.030 Uiso 1 1 calc R
C20 C 1.02337(13) 0.36109(13) -0.20280(10) 0.0243(4) Uani 1 1 d .
C21 C 1.11488(13) 0.31929(13) -0.22811(11) 0.0270(4) Uani 1 1 d .
H21A H 1.1787 0.3598 -0.2212 0.032 Uiso 1 1 calc R
C22 C 1.11152(13) 0.21773(14) -0.26362(11) 0.0260(4) Uani 1 1 d .
C23 C 1.01689(13) 0.15583(14) -0.27153(11) 0.0272(4) Uani 1 1 d .
H23A H 1.0139 0.0884 -0.2966 0.033 Uiso 1 1 calc R
C24 C 0.82974(14) 0.12323(14) -0.24447(11) 0.0287(4) Uani 1 1 d .
C25 C 1.02648(14) 0.47441(14) -0.16974(11) 0.0264(4) Uani 1 1 d .
C26 C 1.21270(14) 0.17686(14) -0.28816(12) 0.0316(4) Uani 1 1 d .
OW1A O 0.2778(6) -0.5264(5) 0.0272(5) 0.106(2) Uani 0.50 1 d P
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
O2 Zn1 O5 112.91(5) . .
O2 Zn1 O6 131.86(5) . 2_644
O5 Zn1 O6 107.04(5) . 2_644
O2 Zn1 O3 92.73(5) . .
O5 Zn1 O3 114.73(5) . .
O6 Zn1 O3 94.08(5) 2_644 .
O2 Zn1 O4 87.78(5) . .
O5 Zn1 O4 58.90(5) . .
O6 Zn1 O4 90.72(5) 2_644 .
O3 Zn1 O4 173.06(5) . .
O2 Zn1 C24 99.53(5) . .
O5 Zn1 C24 30.13(5) . .
O6 Zn1 C24 101.86(6) 2_644 .
O3 Zn1 C24 144.51(5) . .
O4 Zn1 C24 28.90(5) . .
C1 O2 Zn1 129.29(11) . .
C3 O3 Zn1 122.50(11) . .
C24 O4 Zn1 79.46(10) . .
C24 O5 Zn1 99.19(10) . .
C25 O6 Zn1 122.59(11) . 2_654
C16 N1 C15 112.83(14) . .
C7 N2 C17 118.85(14) . .
C7 N2 C14 118.07(14) . .
C17 N2 C14 109.62(13) . .
C10 N3 C9 119.55(14) . .
C10 N3 C11 119.67(14) . .
C9 N3 C11 120.56(13) . .
O1 C1 O2 122.53(16) . .
O1 C1 C2 117.31(16) . .
O2 C1 C2 120.14(15) . .
C10 C2 C3 119.27(15) . .
C10 C2 C1 115.56(15) . .
C3 C2 C1 125.17(15) . .
O3 C3 C2 125.48(15) . .
O3 C3 C4 118.68(15) . .
C2 C3 C4 115.84(15) . .
C9 C4 C5 117.61(14) . .
C9 C4 C3 121.81(15) . .
C5 C4 C3 120.56(15) . .
C6 C5 C4 120.12(16) . .
C5 C6 F1 118.17(15) . .
C5 C6 C7 123.60(16) . .
F1 C6 C7 118.21(15) . .
C8 C7 N2 123.78(15) . .
C8 C7 C6 116.21(15) . .
N2 C7 C6 119.93(15) . .
C7 C8 C9 121.08(16) . .
N3 C9 C8 120.41(15) . .
N3 C9 C4 118.44(14) . .
C8 C9 C4 121.10(15) . .
N3 C10 C2 124.93(16) . .
N3 C11 C13 119.43(17) . .
N3 C11 C12 118.71(17) . .
C13 C11 C12 60.09(15) . .
C11 C12 C13 59.57(14) . .
C11 C13 C12 60.34(14) . .
N2 C14 C15 111.35(15) . .
N1 C15 C14 110.31(15) . .
N1 C16 C17 110.61(15) . .
N2 C17 C16 112.73(14) . .
C23 C18 C19 119.29(15) . .
C23 C18 C24 120.07(15) . .
C19 C18 C24 120.61(15) . .
C20 C19 C18 120.68(15) . .
C19 C20 C21 119.34(16) . .
C19 C20 C25 121.21(14) . .
C21 C20 C25 119.45(14) . .
C22 C21 C20 120.41(15) . .
C21 C22 C23 119.66(15) . .
C21 C22 C26 117.79(15) . .
C23 C22 C26 122.47(16) . .
C18 C23 C22 120.47(16) . .
O4 C24 O5 121.94(15) . .
O4 C24 C18 120.64(16) . .
O5 C24 C18 117.38(15) . .
O4 C24 Zn1 71.64(10) . .
O5 C24 Zn1 50.69(8) . .
C18 C24 Zn1 165.23(13) . .
O7 C25 O6 123.41(16) . .
O7 C25 C20 119.93(15) . .
O6 C25 C20 116.66(15) . .
O8 C26 O9 122.76(16) . .
O8 C26 C22 123.09(17) . .
O9 C26 C22 114.13(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 1.9423(13) .
Zn1 O5 1.9774(12) .
Zn1 O6 1.9933(14) 2_644
Zn1 O3 1.9994(12) .
Zn1 O4 2.4356(13) .
Zn1 C24 2.5230(16) .
F1 C6 1.3577(19) .
O1 C1 1.239(2) .
OW1 OW1A 0.920(8) .
O2 C1 1.272(2) .
O3 C3 1.271(2) .
O4 C24 1.240(2) .
O5 C24 1.283(2) .
O6 C25 1.281(2) .
O6 Zn1 1.9933(14) 2_654
O7 C25 1.233(2) .
O8 C26 1.205(2) .
O9 C26 1.320(2) .
N1 C16 1.483(2) .
N1 C15 1.488(3) .
N2 C7 1.395(2) .
N2 C17 1.465(2) .
N2 C14 1.475(2) .
N3 C10 1.338(2) .
N3 C9 1.395(2) .
N3 C11 1.459(2) .
C1 C2 1.498(2) .
C2 C10 1.367(2) .
C2 C3 1.426(2) .
C3 C4 1.446(2) .
C4 C9 1.408(2) .
C4 C5 1.401(2) .
C5 C6 1.355(2) .
C6 C7 1.413(2) .
C7 C8 1.387(2) .
C8 C9 1.398(2) .
C11 C13 1.474(3) .
C11 C12 1.485(3) .
C12 C13 1.481(3) .
C14 C15 1.518(3) .
C16 C17 1.510(2) .
C18 C23 1.385(2) .
C18 C19 1.392(2) .
C18 C24 1.495(2) .
C19 C20 1.390(2) .
C20 C21 1.390(2) .
C20 C25 1.503(2) .
C21 C22 1.385(2) .
C22 C23 1.393(2) .
C22 C26 1.488(2) .
