#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:14:06 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179563 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/32/4503267.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_4503267
loop_
_publ_author_name
'Llinàs, Antonio'
'Burley, Jonathan C.'
'Prior, Timothy J.'
'Glen, Robert C.'
'Goodman, Jonathan M.'
_publ_section_title
;
 Concomitant Hydrate Polymorphism in the Precipitation of Sparfloxacin
 from Aqueous Solution
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              114
_journal_paper_doi               10.1021/cg700908m
_journal_volume                  8
_journal_year                    2008
_chemical_absolute_configuration
;
 1699 Friedel pairs were averaged for the refinement.
;
_chemical_formula_moiety         'C19 H22 F2 N4 O3, 3(H2 O)'
_chemical_formula_sum            'C19 H28 F2 N4 O6'
_chemical_formula_weight         446.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 109.221(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1533(3)
_cell_length_b                   10.3248(4)
_cell_length_c                   11.9341(4)
_cell_measurement_reflns_used    7330
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1064.97(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8029
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.020
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0373
_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)+(0.0457P)²+0.2055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                2259
_reflns_number_total             2556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg700908m-file003.cif
_cod_data_source_block           Sparfloxacin_single_crystal
_cod_original_cell_volume        1064.97(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4503267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.67641(15) 0.22475(17) 1.08049(11) 0.0283(4) Uani 1 1 d .
F3 F 0.14425(17) 0.27813(17) 0.87298(11) 0.0292(4) Uani 1 1 d .
O1 O 0.17537(19) 0.09177(18) 1.46465(15) 0.0236(4) Uani 1 1 d .
O2 O -0.03596(18) 0.21294(19) 1.38587(14) 0.0242(4) Uani 1 1 d .
O3 O 0.42053(18) 0.18541(18) 1.39702(14) 0.0226(4) Uani 1 1 d .
N1 N 0.0811(2) 0.2887(2) 1.08951(17) 0.0191(4) Uani 1 1 d .
N2 N 0.4336(3) 0.2547(2) 0.86358(17) 0.0270(5) Uani 1 1 d .
N3 N 0.4359(2) 0.2350(2) 0.63009(17) 0.0196(4) Uani 1 1 d .
H3A H 0.520(3) 0.283(3) 0.635(2) 0.023 Uiso 1 1 d .
H3B H 0.397(3) 0.202(3) 0.553(3) 0.023 Uiso 1 1 d .
N4 N 0.6276(2) 0.2040(2) 1.28940(17) 0.0240(5) Uani 1 1 d .
H4A H 0.7215 0.1990 1.2848 0.029 Uiso 1 1 calc R
H4B H 0.6137 0.1972 1.3587 0.029 Uiso 1 1 calc R
C1 C 0.0489(3) 0.2585(2) 1.18921(19) 0.0188(5) Uani 1 1 d .
H1 H -0.0545 0.2706 1.1881 0.023 Uiso 1 1 calc R
C2 C 0.1532(2) 0.2122(2) 1.29079(19) 0.0180(5) Uani 1 1 d .
C3 C 0.3153(2) 0.2080(2) 1.30069(18) 0.0166(4) Uani 1 1 d .
C4 C 0.3500(3) 0.2324(2) 1.19152(19) 0.0180(5) Uani 1 1 d .
C5 C 0.2291(3) 0.2654(2) 1.08468(19) 0.0183(5) Uani 1 1 d .
C6 C 0.2611(3) 0.2710(3) 0.97874(19) 0.0214(5) Uani 1 1 d .
C7 C 0.4096(3) 0.2541(3) 0.9730(2) 0.0218(5) Uani 1 1 d .
C8 C 0.5267(3) 0.2331(3) 1.0801(2) 0.0209(5) Uani 1 1 d .
C9 C 0.5046(3) 0.2222(3) 1.18974(19) 0.0185(5) Uani 1 1 d .
C10 C 0.0938(3) 0.1694(2) 1.3888(2) 0.0188(5) Uani 1 1 d .
C11 C 0.3840(3) 0.3648(3) 0.7831(2) 0.0242(5) Uani 1 1 d .
H11A H 0.4736 0.4219 0.7903 0.029 Uiso 1 1 calc R
H11B H 0.3056 0.4158 0.8047 0.029 Uiso 1 1 calc R
C12 C 0.3157(3) 0.3171(3) 0.6560(2) 0.0228(5) Uani 1 1 d .
H12 H 0.2230 0.2623 0.6491 0.027 Uiso 1 1 calc R
C13 C 0.4873(3) 0.1230(3) 0.7139(2) 0.0237(5) Uani 1 1 d .
H13 H 0.3959 0.0665 0.7067 0.028 Uiso 1 1 calc R
C14 C 0.5500(3) 0.1745(3) 0.8396(2) 0.0243(5) Uani 1 1 d .
H14A H 0.5775 0.1014 0.8964 0.029 Uiso 1 1 calc R
H14B H 0.6445 0.2261 0.8495 0.029 Uiso 1 1 calc R
C15 C 0.6066(3) 0.0449(3) 0.6796(2) 0.0301(6) Uani 1 1 d .
H15A H 0.5580 0.0060 0.6012 0.045 Uiso 1 1 calc R
H15B H 0.6479 -0.0237 0.7383 0.045 Uiso 1 1 calc R
H15C H 0.6911 0.1020 0.6771 0.045 Uiso 1 1 calc R
C16 C -0.0400(3) 0.3477(3) 0.9912(2) 0.0230(5) Uani 1 1 d .
H16 H -0.0977 0.2883 0.9253 0.028 Uiso 1 1 calc R
C17 C -0.0159(3) 0.4828(3) 0.9561(3) 0.0329(6) Uani 1 1 d .
H17A H -0.0562 0.5050 0.8707 0.040 Uiso 1 1 calc R
H17B H 0.0815 0.5270 1.0017 0.040 Uiso 1 1 calc R
C18 C -0.1314(3) 0.4563(3) 1.0181(2) 0.0323(6) Uani 1 1 d .
H18A H -0.1049 0.4842 1.1018 0.039 Uiso 1 1 calc R
H18B H -0.2426 0.4622 0.9708 0.039 Uiso 1 1 calc R
C19 C 0.2680(3) 0.4263(3) 0.5666(2) 0.0243(5) Uani 1 1 d .
H19A H 0.2301 0.3903 0.4862 0.036 Uiso 1 1 calc R
H19B H 0.3573 0.4823 0.5745 0.036 Uiso 1 1 calc R
H19C H 0.1857 0.4772 0.5813 0.036 Uiso 1 1 calc R
O1W O 0.1060(2) -0.0155(2) 0.65674(16) 0.0301(4) Uani 1 1 d D
H1W1 H 0.130(4) 0.015(4) 0.588(2) 0.045 Uiso 1 1 d D
H1W2 H 0.069(4) -0.105(2) 0.645(3) 0.045 Uiso 1 1 d D
O2W O -0.0930(2) 0.2062(2) 0.60085(18) 0.0377(5) Uani 1 1 d D
H2W1 H -0.073(4) 0.210(4) 0.526(2) 0.057 Uiso 1 1 d D
H2W2 H -0.036(4) 0.133(3) 0.642(3) 0.057 Uiso 1 1 d D
O3W O 0.2930(2) -0.1209(2) 1.35283(18) 0.0331(5) Uani 1 1 d D
H3W2 H 0.221(4) -0.181(4) 1.372(4) 0.083(15) Uiso 1 1 d D
H3W1 H 0.279(5) -0.045(3) 1.397(3) 0.077(13) Uiso 1 1 d D
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 119.48(19)
C1 N1 C16 118.4(2)
C5 N1 C16 122.06(19)
C7 N2 C14 122.3(2)
C7 N2 C11 120.6(2)
C14 N2 C11 113.82(19)
C12 N3 C13 112.87(18)
C12 N3 H3A 110.2(19)
C13 N3 H3A 108.1(18)
C12 N3 H3B 110.0(16)
C13 N3 H3B 108.0(19)
H3A N3 H3B 107(2)
C9 N4 H4A 120.0
C9 N4 H4B 120.0
H4A N4 H4B 120.0
N1 C1 C2 124.9(2)
N1 C1 H1 117.5
C2 C1 H1 117.5
C1 C2 C3 118.9(2)
C1 C2 C10 117.8(2)
C3 C2 C10 123.26(19)
O3 C3 C2 122.44(19)
O3 C3 C4 121.53(19)
C2 C3 C4 116.03(18)
C9 C4 C5 119.02(19)
C9 C4 C3 120.55(19)
C5 C4 C3 120.42(19)
C6 C5 N1 121.9(2)
C6 C5 C4 119.3(2)
N1 C5 C4 118.78(19)
F3 C6 C5 120.6(2)
F3 C6 C7 116.23(19)
C5 C6 C7 122.7(2)
C8 C7 N2 123.5(2)
C8 C7 C6 116.31(19)
N2 C7 C6 120.2(2)
F1 C8 C7 118.68(19)
F1 C8 C9 116.50(19)
C7 C8 C9 124.8(2)
N4 C9 C8 120.0(2)
N4 C9 C4 122.6(2)
C8 C9 C4 117.38(19)
O1 C10 O2 125.4(2)
O1 C10 C2 117.7(2)
O2 C10 C2 116.8(2)
N2 C11 C12 109.9(2)
N2 C11 H11A 109.7
C12 C11 H11A 109.7
N2 C11 H11B 109.7
C12 C11 H11B 109.7
H11A C11 H11B 108.2
N3 C12 C19 109.7(2)
N3 C12 C11 107.5(2)
C19 C12 C11 112.9(2)
N3 C12 H12 108.9
C19 C12 H12 108.9
C11 C12 H12 108.9
N3 C13 C14 108.8(2)
N3 C13 C15 108.99(19)
C14 C13 C15 112.4(2)
N3 C13 H13 108.8
C14 C13 H13 108.8
C15 C13 H13 108.8
N2 C14 C13 109.41(19)
N2 C14 H14A 109.8
C13 C14 H14A 109.8
N2 C14 H14B 109.8
C13 C14 H14B 109.8
H14A C14 H14B 108.2
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N1 C16 C17 118.2(2)
N1 C16 C18 118.2(2)
C17 C16 C18 60.30(19)
N1 C16 H16 116.2
C17 C16 H16 116.2
C18 C16 H16 116.2
C16 C17 C18 59.94(18)
C16 C17 H17A 117.8
C18 C17 H17A 117.8
C16 C17 H17B 117.8
C18 C17 H17B 117.8
H17A C17 H17B 114.9
C16 C18 C17 59.76(19)
C16 C18 H18A 117.8
C17 C18 H18A 117.8
C16 C18 H18B 117.8
C17 C18 H18B 117.8
H18A C18 H18B 114.9
C12 C19 H19A 109.5
C12 C19 H19B 109.5
H19A C19 H19B 109.5
C12 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
H1W1 O1W H1W2 110(3)
H2W1 O2W H2W2 105(3)
H3W2 O3W H3W1 100(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C8 1.371(2)
F3 C6 1.362(3)
O1 C10 1.255(3)
O2 C10 1.259(3)
O3 C3 1.255(3)
N1 C1 1.353(3)
N1 C5 1.396(3)
N1 C16 1.456(3)
N2 C7 1.393(3)
N2 C14 1.451(3)
N2 C11 1.461(3)
N3 C12 1.500(3)
N3 C13 1.500(3)
N3 H3A 0.90(3)
N3 H3B 0.94(3)
N4 C9 1.355(3)
N4 H4A 0.8800
N4 H4B 0.8800
C1 C2 1.360(3)
C1 H1 0.9500
C2 C3 1.450(3)
C2 C10 1.510(3)
C3 C4 1.461(3)
C4 C9 1.427(3)
C4 C5 1.427(3)
C5 C6 1.390(3)
C6 C7 1.395(3)
C7 C8 1.389(3)
C8 C9 1.392(3)
C11 C12 1.520(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C19 1.515(4)
C12 H12 1.0000
C13 C14 1.515(3)
C13 C15 1.519(4)
C13 H13 1.0000
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C17 1.493(4)
C16 C18 1.496(4)
C16 H16 1.0000
C17 C18 1.501(4)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
O1W H1W1 0.969(19)
O1W H1W2 0.976(19)
O2W H2W1 0.966(19)
O2W H2W2 0.953(19)
O3W H3W2 0.98(2)
O3W H3W1 0.98(2)
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
C5 N1 C1 C2 3.7(4)
C16 N1 C1 C2 -174.8(2)
N1 C1 C2 C3 7.7(4)
N1 C1 C2 C10 -173.2(2)
C1 C2 C3 O3 169.0(2)
C10 C2 C3 O3 -10.1(4)
C1 C2 C3 C4 -10.7(3)
C10 C2 C3 C4 170.2(2)
O3 C3 C4 C9 4.4(4)
C2 C3 C4 C9 -175.9(2)
O3 C3 C4 C5 -176.3(2)
C2 C3 C4 C5 3.4(3)
C1 N1 C5 C6 167.6(2)
C16 N1 C5 C6 -13.9(4)
C1 N1 C5 C4 -11.2(3)
C16 N1 C5 C4 167.3(2)
C9 C4 C5 C6 7.9(3)
C3 C4 C5 C6 -171.4(2)
C9 C4 C5 N1 -173.3(2)
C3 C4 C5 N1 7.4(3)
N1 C5 C6 F3 -11.1(4)
C4 C5 C6 F3 167.7(2)
N1 C5 C6 C7 176.9(2)
C4 C5 C6 C7 -4.4(4)
C14 N2 C7 C8 32.1(4)
C11 N2 C7 C8 -126.3(3)
C14 N2 C7 C6 -145.7(3)
C11 N2 C7 C6 55.8(4)
F3 C6 C7 C8 -173.4(2)
C5 C6 C7 C8 -1.0(4)
F3 C6 C7 N2 4.6(4)
C5 C6 C7 N2 177.0(2)
N2 C7 C8 F1 6.5(4)
C6 C7 C8 F1 -175.5(2)
N2 C7 C8 C9 -175.0(3)
C6 C7 C8 C9 3.0(4)
F1 C8 C9 N4 -0.3(4)
C7 C8 C9 N4 -178.8(3)
F1 C8 C9 C4 179.2(2)
C7 C8 C9 C4 0.6(4)
C5 C4 C9 N4 173.3(2)
C3 C4 C9 N4 -7.4(4)
C5 C4 C9 C8 -6.1(3)
C3 C4 C9 C8 173.2(2)
C1 C2 C10 O1 158.3(2)
C3 C2 C10 O1 -22.6(3)
C1 C2 C10 O2 -20.3(3)
C3 C2 C10 O2 158.8(2)
C7 N2 C11 C12 -140.0(2)
C14 N2 C11 C12 59.8(3)
C13 N3 C12 C19 -179.0(2)
C13 N3 C12 C11 57.9(3)
N2 C11 C12 N3 -56.4(3)
N2 C11 C12 C19 -177.5(2)
C12 N3 C13 C14 -57.9(3)
C12 N3 C13 C15 179.2(2)
C7 N2 C14 C13 141.4(2)
C11 N2 C14 C13 -58.8(3)
N3 C13 C14 N2 55.5(3)
C15 C13 C14 N2 176.3(2)
C1 N1 C16 C17 115.3(3)
C5 N1 C16 C17 -63.2(3)
C1 N1 C16 C18 45.8(3)
C5 N1 C16 C18 -132.7(2)
N1 C16 C17 C18 -108.1(3)
N1 C16 C18 C17 108.2(3)
