#------------------------------------------------------------------------------
#$Date: 2017-09-22 17:42:43 +0300 (Fri, 22 Sep 2017) $
#$Revision: 201174 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/73/1547309.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_1547309
loop_
_publ_author_name
'N.N. Golovnev'
'M.S. Molokeev'
'M.K. Lesnikov'
'I.V. Sterkhova'
'V.V. Atuchin'
_publ_section_title
;
 Thiobarbiturate and barbiturate salts of pefloxacin drug: Growth,
 structure, thermal stability and IR-spectra
;
_journal_issue                   0
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              367
_journal_page_last               372
_journal_paper_doi               10.1016/j.molstruc.2017.08.011
_journal_volume                  1149
_journal_year                    2017
_chemical_formula_moiety
;
C17 H21 F N3 O3, C4 H3 N2 O2 S, 3(H2 O)
;
_chemical_formula_sum            'C21 H30 F N5 O8 S'
_chemical_formula_weight         531.56
_chemical_name_systematic
;
2-thiobarbiturate trihydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.484(2)
_cell_angle_beta                 88.735(2)
_cell_angle_gamma                78.147(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4651(6)
_cell_length_b                   9.3753(6)
_cell_length_c                   15.8077(9)
_cell_measurement_reflns_used    11839
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.636
_cell_measurement_theta_min      1.288
_cell_volume                     1227.48(14)
_computing_cell_refinement       'APEX2 (Bruker, 2003-2008)'
_computing_data_collection       'APEX2 (Bruker, 2003-2008)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0473
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11838
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.459
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5647
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0628P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3139
_reflns_number_total             5647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            PefHHtba_3H2O.cif
_cod_data_source_block           d
_cod_database_code               1547309
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 1.15387(9) 0.12889(8) 0.06456(4) 0.02330(18) Uani 1 1 d . . . . .
O1B O 1.3240(2) 0.0827(2) 0.36100(11) 0.0311(5) Uani 1 1 d . . . . .
O2B O 0.8586(2) 0.4336(2) 0.29034(11) 0.0317(5) Uani 1 1 d . . . . .
N1B N 1.0107(2) 0.2885(2) 0.19257(13) 0.0207(5) Uani 1 1 d . . . . .
H1B H 0.9482 0.3348 0.1548 0.025 Uiso 1 1 calc R U . . .
N3B N 1.2275(3) 0.1112(2) 0.22752(12) 0.0201(5) Uani 1 1 d . . . . .
H3B H 1.3018 0.0378 0.2132 0.024 Uiso 1 1 calc R U . . .
C2B C 1.1296(3) 0.1781(3) 0.16530(15) 0.0183(6) Uani 1 1 d . . . . .
C4B C 1.2174(3) 0.1518(3) 0.31234(16) 0.0210(6) Uani 1 1 d . . . . .
C5B C 1.0906(3) 0.2640(3) 0.33576(16) 0.0236(6) Uani 1 1 d . . . . .
H5B H 1.0788 0.2931 0.3920 0.028 Uiso 1 1 calc R U . . .
C6B C 0.9798(3) 0.3348(3) 0.27673(16) 0.0224(6) Uani 1 1 d . . . . .
O1 O 0.7956(2) 0.5032(2) 0.10569(11) 0.0269(5) Uani 1 1 d . . . . .
O2 O 0.6617(2) 0.6937(2) 0.21167(11) 0.0267(5) Uani 1 1 d D . . . .
H2 H 0.727(3) 0.622(3) 0.1838(16) 0.032 Uiso 1 1 d D U . . .
O3 O 0.4641(2) 0.8696(2) 0.17060(11) 0.0323(5) Uani 1 1 d . . . . .
F F 0.95186(19) 0.22728(17) -0.16345(9) 0.0342(4) Uani 1 1 d . . . . .
N1 N 0.7693(3) 0.2659(2) -0.45973(13) 0.0247(5) Uani 1 1 d . . . . .
H0 H 0.7890 0.3544 -0.4879 0.030 Uiso 1 1 calc R U . . .
N2 N 0.7495(3) 0.3628(2) -0.28789(13) 0.0234(5) Uani 1 1 d . . . . .
N3 N 0.4959(2) 0.7162(2) -0.07617(13) 0.0184(5) Uani 1 1 d . . . . .
C1 C 0.9054(3) 0.3303(3) -0.33418(16) 0.0251(6) Uani 1 1 d . . . . .
H01A H 0.9916 0.2961 -0.2949 0.030 Uiso 1 1 calc R U . . .
H01B H 0.9254 0.4182 -0.3614 0.030 Uiso 1 1 calc R U . . .
C2 C 0.9034(3) 0.2148(3) -0.40019(16) 0.0276(7) Uani 1 1 d . . . . .
H02A H 1.0056 0.1949 -0.4312 0.033 Uiso 1 1 calc R U . . .
H02B H 0.8889 0.1253 -0.3728 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6120(3) 0.3046(3) -0.41221(17) 0.0284(7) Uani 1 1 d . . . . .
H03A H 0.5877 0.2178 -0.3856 0.034 Uiso 1 1 calc R U . . .
H03B H 0.5266 0.3424 -0.4513 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6181(3) 0.4178(3) -0.34517(16) 0.0258(6) Uani 1 1 d . . . . .
H04A H 0.6348 0.5072 -0.3718 0.031 Uiso 1 1 calc R U . . .
H04B H 0.5164 0.4390 -0.3136 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8349(3) 0.3976(3) -0.06153(16) 0.0211(6) Uani 1 1 d . . . . .
H05 H 0.9062 0.3488 -0.0219 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8434(3) 0.3500(3) -0.14274(17) 0.0231(6) Uani 1 1 d . . . . .
C7 C 0.7418(3) 0.4211(3) -0.20669(16) 0.0220(6) Uani 1 1 d . . . . .
C8 C 0.6283(3) 0.5442(3) -0.18316(16) 0.0218(6) Uani 1 1 d . . . . .
H08 H 0.5607 0.5947 -0.2238 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6137(3) 0.5938(3) -0.09944(15) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.7177(3) 0.5210(3) -0.03743(16) 0.0190(6) Uani 1 1 d . . . . .
C11 C 0.7049(3) 0.5699(3) 0.04888(16) 0.0196(6) Uani 1 1 d . . . . .
C12 C 0.5843(3) 0.6961(3) 0.06708(15) 0.0171(6) Uani 1 1 d . . . . .
C13 C 0.4860(3) 0.7637(3) 0.00361(15) 0.0191(6) Uani 1 1 d . . . . .
H13 H 0.4088 0.8466 0.0171 0.023 Uiso 1 1 calc R U . . .
C14 C 0.5631(3) 0.7603(3) 0.15246(16) 0.0213(6) Uani 1 1 d . . . . .
C15 C 0.3899(3) 0.7936(3) -0.14376(16) 0.0250(6) Uani 1 1 d . . . . .
H15A H 0.3357 0.7243 -0.1701 0.030 Uiso 1 1 calc R U . . .
H15B H 0.4575 0.8269 -0.1868 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2643(3) 0.9218(3) -0.11394(17) 0.0278(7) Uani 1 1 d . . . . .
H16A H 0.2020 0.9648 -0.1611 0.033 Uiso 1 1 calc R U . . .
H16B H 0.1944 0.8899 -0.0725 0.033 Uiso 1 1 calc R U . . .
H16C H 0.3164 0.9927 -0.0892 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7638(4) 0.1558(3) -0.52619(19) 0.0415(9) Uani 1 1 d . . . . .
H17A H 0.6763 0.1920 -0.5634 0.050 Uiso 1 1 calc R U . . .
H17B H 0.8637 0.1374 -0.5580 0.050 Uiso 1 1 calc R U . . .
H17C H 0.7477 0.0669 -0.5000 0.050 Uiso 1 1 calc R U . . .
O1W O 0.6420(3) 0.9423(2) 0.33863(12) 0.0332(5) Uani 1 1 d D . . . .
H11W H 0.544(3) 0.990(3) 0.3429(19) 0.040 Uiso 1 1 d D U . . .
H12W H 0.653(3) 0.877(3) 0.2995(16) 0.040 Uiso 1 1 d D U . . .
O2W O 0.7217(3) 0.7849(2) 0.48442(13) 0.0360(5) Uani 1 1 d D . . . .
H21W H 0.697(3) 0.832(3) 0.5341(15) 0.043 Uiso 1 1 d D U . . .
H22W H 0.693(4) 0.837(3) 0.4392(16) 0.043 Uiso 1 1 d D U . . .
O3W O 0.7847(3) 0.4980(2) 0.44932(13) 0.0443(6) Uani 1 1 d D . . . .
H31W H 0.775(4) 0.584(3) 0.465(2) 0.053 Uiso 1 1 d D U . . .
H32W H 0.802(4) 0.483(3) 0.3944(15) 0.053 Uiso 1 1 d D U . . .
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'
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'
S S 0.1246 0.1234 '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
C2B N1B C6B 126.2(2) . .
C2B N3B C4B 125.5(2) . .
N1B C2B N3B 114.4(2) . .
N1B C2B S 122.7(2) . .
N3B C2B S 123.0(2) . .
O1B C4B C5B 126.0(2) . .
O1B C4B N3B 117.3(2) . .
C5B C4B N3B 116.7(2) . .
C4B C5B C6B 121.6(2) . .
O2B C6B C5B 127.6(2) . .
O2B C6B N1B 117.0(2) . .
C5B C6B N1B 115.4(2) . .
C17 N1 C2 111.6(2) . .
C17 N1 C3 111.2(2) . .
C2 N1 C3 110.3(2) . .
C7 N2 C4 118.5(2) . .
C7 N2 C1 119.4(2) . .
C4 N2 C1 110.8(2) . .
C13 N3 C9 119.9(2) . .
C13 N3 C15 122.1(2) . .
C9 N3 C15 117.9(2) . .
N2 C1 C2 109.9(2) . .
N1 C2 C1 109.8(2) . .
N1 C3 C4 110.9(2) . .
N2 C4 C3 109.5(2) . .
C6 C5 C10 119.9(2) . .
F C6 C5 118.8(2) . .
F C6 C7 118.1(2) . .
C5 C6 C7 123.0(3) . .
C8 C7 N2 122.3(2) . .
C8 C7 C6 117.0(2) . .
N2 C7 C6 120.6(2) . .
C7 C8 C9 121.4(2) . .
C8 C9 N3 120.8(2) . .
C8 C9 C10 120.2(2) . .
N3 C9 C10 119.1(2) . .
C9 C10 C5 118.5(2) . .
C9 C10 C11 121.2(2) . .
C5 C10 C11 120.3(2) . .
O1 C11 C12 122.0(2) . .
O1 C11 C10 121.7(2) . .
C12 C11 C10 116.3(2) . .
C13 C12 C11 120.1(2) . .
C13 C12 C14 118.3(2) . .
C11 C12 C14 121.6(2) . .
N3 C13 C12 123.5(2) . .
O3 C14 O2 119.4(2) . .
O3 C14 C12 124.0(3) . .
O2 C14 C12 116.7(2) . .
N3 C15 C16 115.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C2B 1.659(3) .
O1B C4B 1.268(3) .
O2B C6B 1.249(3) .
N1B C2B 1.353(3) .
N1B C6B 1.405(3) .
N3B C2B 1.364(3) .
N3B C4B 1.393(3) .
C4B C5B 1.386(3) .
C5B C6B 1.401(4) .
O1 C11 1.269(3) .
O2 C14 1.331(3) .
O3 C14 1.215(3) .
F C6 1.354(3) .
N1 C17 1.488(3) .
N1 C2 1.490(3) .
N1 C3 1.493(3) .
N2 C7 1.394(3) .
N2 C4 1.457(3) .
N2 C1 1.471(3) .
N3 C13 1.336(3) .
N3 C9 1.403(3) .
N3 C15 1.495(3) .
C1 C2 1.513(3) .
C3 C4 1.515(4) .
C5 C6 1.358(3) .
C5 C10 1.410(3) .
C6 C7 1.413(4) .
C7 C8 1.389(4) .
C8 C9 1.401(3) .
C9 C10 1.407(3) .
C10 C11 1.438(3) .
C11 C12 1.422(3) .
C12 C13 1.382(3) .
C12 C14 1.475(3) .
C15 C16 1.504(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6B N1B C2B N3B -1.6(4) . . . .
C6B N1B C2B S 178.47(19) . . . .
C4B N3B C2B N1B -2.9(3) . . . .
C4B N3B C2B S 177.0(2) . . . .
C2B N3B C4B O1B -176.1(2) . . . .
C2B N3B C4B C5B 4.2(4) . . . .
O1B C4B C5B C6B 179.3(3) . . . .
N3B C4B C5B C6B -1.1(4) . . . .
C4B C5B C6B O2B 177.7(3) . . . .
C4B C5B C6B N1B -2.7(4) . . . .
C2B N1B C6B O2B -176.0(2) . . . .
C2B N1B C6B C5B 4.3(4) . . . .
C7 N2 C1 C2 156.1(2) . . . .
C4 N2 C1 C2 -60.7(3) . . . .
C17 N1 C2 C1 179.6(2) . . . .
C3 N1 C2 C1 -56.4(3) . . . .
N2 C1 C2 N1 58.4(3) . . . .
C17 N1 C3 C4 -179.5(2) . . . .
C2 N1 C3 C4 56.2(3) . . . .
C7 N2 C4 C3 -156.8(2) . . . .
C1 N2 C4 C3 59.7(3) . . . .
N1 C3 C4 N2 -57.4(3) . . . .
C10 C5 C6 F -177.0(2) . . . .
C10 C5 C6 C7 1.8(4) . . . .
C4 N2 C7 C8 -10.5(4) . . . .
C1 N2 C7 C8 129.9(3) . . . .
C4 N2 C7 C6 164.9(2) . . . .
C1 N2 C7 C6 -54.7(3) . . . .
F C6 C7 C8 178.1(2) . . . .
C5 C6 C7 C8 -0.7(4) . . . .
F C6 C7 N2 2.4(4) . . . .
C5 C6 C7 N2 -176.3(2) . . . .
N2 C7 C8 C9 174.5(2) . . . .
C6 C7 C8 C9 -1.1(4) . . . .
C7 C8 C9 N3 -178.5(2) . . . .
C7 C8 C9 C10 1.6(4) . . . .
C13 N3 C9 C8 -178.6(2) . . . .
C15 N3 C9 C8 -1.4(3) . . . .
C13 N3 C9 C10 1.3(3) . . . .
C15 N3 C9 C10 178.5(2) . . . .
C8 C9 C10 C5 -0.5(4) . . . .
N3 C9 C10 C5 179.6(2) . . . .
C8 C9 C10 C11 -180.0(2) . . . .
N3 C9 C10 C11 0.1(4) . . . .
C6 C5 C10 C9 -1.2(4) . . . .
C6 C5 C10 C11 178.3(2) . . . .
C9 C10 C11 O1 178.4(2) . . . .
C5 C10 C11 O1 -1.1(4) . . . .
C9 C10 C11 C12 -1.1(3) . . . .
C5 C10 C11 C12 179.4(2) . . . .
O1 C11 C12 C13 -178.7(2) . . . .
C10 C11 C12 C13 0.7(3) . . . .
O1 C11 C12 C14 2.9(4) . . . .
C10 C11 C12 C14 -177.7(2) . . . .
C9 N3 C13 C12 -1.7(4) . . . .
C15 N3 C13 C12 -178.8(2) . . . .
C11 C12 C13 N3 0.6(4) . . . .
C14 C12 C13 N3 179.1(2) . . . .
C13 C12 C14 O3 0.0(4) . . . .
C11 C12 C14 O3 178.4(2) . . . .
C13 C12 C14 O2 -178.9(2) . . . .
C11 C12 C14 O2 -0.5(4) . . . .
C13 N3 C15 C16 -4.0(3) . . . .
C9 N3 C15 C16 178.8(2) . . . .
