#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:57:40 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179872 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/68/7016834.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_7016834
loop_
_publ_author_name
'Tarushi, Alketa'
'Polatoglou, Eleni'
'Kljun, Jakob'
'Turel, Iztok'
'Psomas, George'
'Kessissoglou, Dimitris P.'
_publ_section_title
;
 Interaction of Zn(ii) with quinolone drugs: Structure and biological
 evaluation.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9461
_journal_page_last               9473
_journal_paper_doi               10.1039/c1dt10870k
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C50 H50 F4 N10 O6 Zn, 4(C H4 O)'
_chemical_formula_sum            'C54 H66 F4 N10 O10 Zn'
_chemical_formula_weight         1156.54
_chemical_name_common
;
((1,10-phenanthroline)di(5-amino-1-cyclopropyl-7-((3S,5R)-3,5-
dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-
carboxylato-kappa$2!O,O)zinc(ii)) bis methanol solvate
;
_chemical_name_systematic
;
[(1,10-phenanthroline)di(5-amino-1-cyclopropyl-7-((3S,5R)-3,5-
dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylato-
κ²O,O)zinc(II)] bis methanol solvate
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.774(5)
_cell_length_b                   15.850(5)
_cell_length_c                   23.734(5)
_cell_measurement_reflns_used    6952
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      0.41
_cell_volume                     5558(3)
_computing_cell_refinement       'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinovski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12083
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.9258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.384
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0517
_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)+(0.0648P)²+6.7471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                4487
_reflns_number_total             6355
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1dt10870k.txt
_cod_data_source_block           1
_cod_database_code               7016834
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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
Zn1 Zn 0.7500 0.2500 0.270323(17) 0.02342(13) Uani 1 2 d S
C01 C 0.62103(19) 0.38126(17) 0.31893(11) 0.0254(6) Uani 1 1 d .
C02 C 0.68738(19) 0.40030(17) 0.36539(11) 0.0245(6) Uani 1 1 d .
C03 C 0.66250(19) 0.45968(17) 0.40421(11) 0.0263(6) Uani 1 1 d .
H03 H 0.6051 0.4857 0.3994 0.032 Uiso 1 1 calc R
C04 C 0.79250(19) 0.44074(16) 0.46125(11) 0.0241(6) Uani 1 1 d .
C05 C 0.82675(18) 0.38183(16) 0.42067(11) 0.0232(5) Uani 1 1 d .
C06 C 0.77763(18) 0.36672(16) 0.36893(11) 0.0234(6) Uani 1 1 d .
C07 C 0.6863(2) 0.56119(18) 0.47868(13) 0.0313(6) Uani 1 1 d .
H07 H 0.6530 0.5534 0.5150 0.038 Uiso 1 1 calc R
C08 C 0.6613(3) 0.6364(2) 0.44455(17) 0.0565(11) Uani 1 1 d .
H08A H 0.6130 0.6738 0.4592 0.068 Uiso 1 1 calc R
H08B H 0.6631 0.6310 0.4030 0.068 Uiso 1 1 calc R
C09 C 0.7495(3) 0.63430(19) 0.47568(15) 0.0455(8) Uani 1 1 d .
H09A H 0.8056 0.6276 0.4533 0.055 Uiso 1 1 calc R
H09B H 0.7555 0.6703 0.5096 0.055 Uiso 1 1 calc R
C10 C 0.90787(18) 0.33647(17) 0.43399(11) 0.0251(6) Uani 1 1 d .
C11 C 0.94803(18) 0.35114(18) 0.48577(11) 0.0256(6) Uani 1 1 d .
C12 C 0.91333(19) 0.40342(17) 0.52771(11) 0.0262(6) Uani 1 1 d .
C13 C 0.8349(2) 0.44864(17) 0.51303(11) 0.0266(6) Uani 1 1 d .
C14 C 1.0005(2) 0.33823(18) 0.60598(12) 0.0301(6) Uani 1 1 d .
H14A H 1.0655 0.3482 0.5983 0.036 Uiso 1 1 calc R
H14B H 0.9831 0.2842 0.5881 0.036 Uiso 1 1 calc R
C15 C 0.9848(2) 0.33319(19) 0.66949(12) 0.0306(6) Uani 1 1 d .
H15 H 0.9198 0.3192 0.6766 0.037 Uiso 1 1 calc R
C16 C 1.0438(2) 0.2651(2) 0.69550(14) 0.0400(8) Uani 1 1 d .
H16A H 1.1076 0.2783 0.6886 0.060 Uiso 1 1 calc R
H16B H 1.0291 0.2105 0.6785 0.060 Uiso 1 1 calc R
H16C H 1.0327 0.2626 0.7362 0.060 Uiso 1 1 calc R
C17 C 0.9642(2) 0.48822(18) 0.60962(12) 0.0303(6) Uani 1 1 d .
H17A H 0.9246 0.5321 0.5930 0.036 Uiso 1 1 calc R
H17B H 1.0279 0.5050 0.6033 0.036 Uiso 1 1 calc R
C18 C 0.9459(2) 0.48120(18) 0.67237(12) 0.0301(6) Uani 1 1 d .
H18 H 0.8814 0.4642 0.6784 0.036 Uiso 1 1 calc R
C19 C 0.9631(2) 0.5653(2) 0.70179(13) 0.0402(8) Uani 1 1 d .
H19A H 0.9557 0.5583 0.7426 0.060 Uiso 1 1 calc R
H19B H 0.9198 0.6074 0.6881 0.060 Uiso 1 1 calc R
H19C H 1.0249 0.5843 0.6937 0.060 Uiso 1 1 calc R
C20 C 0.6431(2) 0.1151(2) 0.20020(18) 0.0467(9) Uani 1 1 d .
H20 H 0.6279 0.0907 0.2355 0.056 Uiso 1 1 calc R
C21 C 0.6081(3) 0.0791(3) 0.1509(2) 0.0647(13) Uani 1 1 d .
H21 H 0.5678 0.0325 0.1533 0.078 Uiso 1 1 calc R
C22 C 0.6312(3) 0.1101(3) 0.1003(2) 0.0651(13) Uani 1 1 d .
H22 H 0.6082 0.0850 0.0669 0.078 Uiso 1 1 calc R
C23 C 0.6899(3) 0.1804(2) 0.09707(14) 0.0489(10) Uani 1 1 d .
C24 C 0.7207(2) 0.21380(19) 0.14844(12) 0.0312(6) Uani 1 1 d .
C25 C 0.7210(3) 0.2173(3) 0.04550(14) 0.0683(16) Uani 1 1 d .
H25 H 0.7003 0.1951 0.0106 0.082 Uiso 1 1 calc R
O26 O 0.54450(13) 0.41653(13) 0.32182(8) 0.0313(5) Uani 1 1 d .
O27 O 0.64275(14) 0.33202(12) 0.27947(8) 0.0303(4) Uani 1 1 d .
O28 O 0.81444(13) 0.32430(13) 0.32982(8) 0.0299(4) Uani 1 1 d .
N29 N 0.71258(16) 0.48430(14) 0.44867(9) 0.0257(5) Uani 1 1 d .
N30 N 0.94730(17) 0.28148(16) 0.39764(10) 0.0316(6) Uani 1 1 d .
H30A H 0.9978 0.2556 0.4071 0.038 Uiso 1 1 calc R
H30B H 0.9224 0.2717 0.3646 0.038 Uiso 1 1 calc R
N31 N 0.94669(17) 0.40688(15) 0.58215(10) 0.0306(5) Uani 1 1 d .
N32 N 1.00550(16) 0.41577(16) 0.69530(10) 0.0303(5) Uani 1 1 d .
H32 H 0.996(2) 0.411(2) 0.7356(14) 0.032(8) Uiso 1 1 d .
N33 N 0.69676(15) 0.18211(15) 0.19917(10) 0.0294(5) Uani 1 1 d .
F34 F 0.79312(12) 0.49220(10) 0.55499(7) 0.0321(4) Uani 1 1 d .
F35 F 1.02811(11) 0.31031(11) 0.49466(7) 0.0340(4) Uani 1 1 d .
C36 C 0.7534(3) 0.5749(3) 0.28679(18) 0.0588(10) Uani 1 1 d .
H36A H 0.6911 0.5600 0.2969 0.088 Uiso 1 1 calc R
H36B H 0.7724 0.5416 0.2541 0.088 Uiso 1 1 calc R
H36C H 0.7565 0.6351 0.2776 0.088 Uiso 1 1 calc R
O37 O 0.81102(17) 0.5577(2) 0.33241(11) 0.0603(8) Uani 1 1 d .
H37 H 0.8650 0.5654 0.3226 0.090 Uiso 1 1 calc R
C38 C 0.8469(4) 0.6531(4) 0.1262(2) 0.0928(18) Uani 1 1 d .
H38A H 0.8314 0.6086 0.1531 0.139 Uiso 1 1 calc R
H38B H 0.7966 0.6613 0.0999 0.139 Uiso 1 1 calc R
H38C H 0.8585 0.7059 0.1465 0.139 Uiso 1 1 calc R
O39 O 0.92575(19) 0.62942(17) 0.09577(11) 0.0538(7) Uani 1 1 d .
H39 H 0.9668 0.6159 0.1185 0.081 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 0.0033 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
O27 Zn1 O27 167.90(11) . 2_655
O27 Zn1 O28 85.58(8) . .
O27 Zn1 O28 86.18(8) 2_655 .
O27 Zn1 O28 86.18(8) . 2_655
O27 Zn1 O28 85.58(8) 2_655 2_655
O28 Zn1 O28 94.00(12) . 2_655
O27 Zn1 N33 96.72(8) . .
O27 Zn1 N33 92.77(9) 2_655 .
O28 Zn1 N33 171.08(9) . .
O28 Zn1 N33 94.75(9) 2_655 .
O27 Zn1 N33 92.77(9) . 2_655
O27 Zn1 N33 96.72(8) 2_655 2_655
O28 Zn1 N33 94.75(9) . 2_655
O28 Zn1 N33 171.08(9) 2_655 2_655
N33 Zn1 N33 76.56(13) . 2_655
O27 C01 O26 122.8(3) . .
O27 C01 C02 120.2(2) . .
O26 C01 C02 117.0(2) . .
C03 C02 C06 117.7(2) . .
C03 C02 C01 117.1(2) . .
C06 C02 C01 124.9(2) . .
N29 C03 C02 125.4(3) . .
C13 C04 N29 121.8(2) . .
C13 C04 C05 119.7(3) . .
N29 C04 C05 118.4(2) . .
C10 C05 C04 118.3(2) . .
C10 C05 C06 121.6(2) . .
C04 C05 C06 120.1(2) . .
O28 C06 C02 123.4(2) . .
O28 C06 C05 119.6(2) . .
C02 C06 C05 117.0(2) . .
N29 C07 C08 117.9(3) . .
N29 C07 C09 117.3(3) . .
C08 C07 C09 60.4(3) . .
C07 C08 C09 59.8(2) . .
C07 C09 C08 59.7(2) . .
N30 C10 C11 119.2(2) . .
N30 C10 C05 122.7(2) . .
C11 C10 C05 118.0(2) . .
F35 C11 C10 115.4(2) . .
F35 C11 C12 119.4(2) . .
C10 C11 C12 125.2(3) . .
N31 C12 C11 124.0(3) . .
N31 C12 C13 120.3(3) . .
C11 C12 C13 115.4(2) . .
F34 C13 C04 119.3(3) . .
F34 C13 C12 116.8(2) . .
C04 C13 C12 123.1(3) . .
N31 C14 C15 109.8(2) . .
N32 C15 C16 110.0(2) . .
N32 C15 C14 109.4(2) . .
C16 C15 C14 110.6(3) . .
N31 C17 C18 109.9(2) . .
N32 C18 C17 108.0(2) . .
N32 C18 C19 110.3(2) . .
C17 C18 C19 110.8(2) . .
N33 C20 C21 122.2(4) . .
C22 C21 C20 120.3(4) . .
C21 C22 C23 119.6(3) . .
C24 C23 C22 116.6(4) . .
C24 C23 C25 119.0(4) . .
C22 C23 C25 124.4(4) . .
N33 C24 C23 123.3(3) . .
N33 C24 C24 117.01(16) . 2_655
C23 C24 C24 119.7(2) . 2_655
C25 C25 C23 121.3(2) 2_655 .
C01 O27 Zn1 131.64(18) . .
C06 O28 Zn1 127.10(18) . .
C03 N29 C04 119.2(2) . .
C03 N29 C07 118.5(2) . .
C04 N29 C07 122.0(2) . .
C12 N31 C14 121.7(2) . .
C12 N31 C17 120.8(2) . .
C14 N31 C17 112.7(2) . .
C18 N32 C15 110.4(2) . .
C20 N33 C24 118.1(3) . .
C20 N33 Zn1 127.2(2) . .
C24 N33 Zn1 114.69(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O27 2.061(2) .
Zn1 O27 2.061(2) 2_655
Zn1 O28 2.071(2) .
Zn1 O28 2.0707(19) 2_655
Zn1 N33 2.151(2) .
Zn1 N33 2.151(2) 2_655
C01 O27 1.261(3) .
C01 O26 1.263(3) .
C01 C02 1.506(4) .
C02 C03 1.367(4) .
C02 C06 1.438(4) .
C03 N29 1.347(4) .
C04 C13 1.385(4) .
C04 N29 1.400(4) .
C04 C05 1.434(4) .
C05 C10 1.433(4) .
C05 C06 1.446(4) .
C06 O28 1.269(3) .
C07 N29 1.464(3) .
C07 C08 1.488(5) .
C07 C09 1.490(5) .
C08 C09 1.498(6) .
C10 N30 1.358(4) .
C10 C11 1.384(4) .
C11 F35 1.365(3) .
C11 C12 1.393(4) .
C12 N31 1.384(4) .
C12 C13 1.406(4) .
C13 F34 1.360(3) .
C14 N31 1.461(4) .
C14 C15 1.527(4) .
C15 N32 1.477(4) .
C15 C16 1.519(4) .
C17 N31 1.468(4) .
C17 C18 1.518(4) .
C18 N32 1.466(4) .
C18 C19 1.527(4) .
C20 N33 1.326(4) .
C20 C21 1.400(6) .
C21 C22 1.342(7) .
C22 C23 1.415(6) .
C23 C24 1.405(4) .
C23 C25 1.432(6) .
C24 N33 1.352(4) .
C24 C24 1.437(7) 2_655
C25 C25 1.345(10) 2_655
C36 O37 1.404(4) .
C38 O39 1.420(6) .
