#------------------------------------------------------------------------------
#$Date: 2017-09-22 17:41:59 +0300 (Fri, 22 Sep 2017) $
#$Revision: 201173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/73/1547308.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_1547308
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
;
_chemical_formula_sum            'C21 H24 F N5 O5 S'
_chemical_formula_weight         477.51
_chemical_name_systematic
;
pefloxacinium 2-thiobarbiturate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.109(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0768(9)
_cell_length_b                   14.7120(11)
_cell_length_c                   12.2222(9)
_cell_measurement_reflns_used    105889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.080
_cell_measurement_theta_min      2.171
_cell_volume                     2162.9(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0869
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            105889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_min         2.171
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7336
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+1.4849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4737
_reflns_number_total             6337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            PefHHtba.cif
_cod_data_source_block           a
_cod_database_code               1547308
_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+1/2, -z+1/2'
'-x, -y, -z'
'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_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 0.76546(3) -0.17198(3) 0.09383(4) 0.02288(11) Uani 1 1 d . . . . .
O1B O 0.94587(9) 0.11133(8) -0.00639(10) 0.0234(2) Uani 1 1 d . . . . .
O2B O 0.55323(9) 0.09683(8) -0.04500(11) 0.0267(3) Uani 1 1 d . . . . .
N1B N 0.65956(10) -0.02138(9) 0.02234(11) 0.0188(3) Uani 1 1 d . . . . .
H1B H 0.5997 -0.0510 0.0314 0.023 Uiso 1 1 calc R U . . .
N3B N 0.84960(10) -0.01530(9) 0.03429(11) 0.0190(3) Uani 1 1 d . . . . .
H3B H 0.9127 -0.0420 0.0478 0.023 Uiso 1 1 calc R U . . .
C2B C 0.75740(12) -0.06372(10) 0.04855(12) 0.0173(3) Uani 1 1 d . . . . .
C4B C 0.85065(12) 0.07528(10) -0.00083(13) 0.0186(3) Uani 1 1 d . . . . .
C5B C 0.74839(13) 0.11601(11) -0.02629(14) 0.0213(3) Uani 1 1 d . . . . .
H5B H 0.7455 0.1764 -0.0488 0.026 Uiso 1 1 calc R U . . .
C6B C 0.64841(12) 0.06795(11) -0.01879(13) 0.0193(3) Uani 1 1 d . . . . .
F F 0.87813(9) 0.53693(7) 0.09253(10) 0.0366(3) Uani 1 1 d . . . . .
O1 O 0.48542(11) 0.64801(8) 0.07883(11) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.28579(12) 0.66227(9) 0.11304(12) 0.0365(3) Uani 1 1 d . . . . .
H2 H 0.361(2) 0.6709(16) 0.095(2) 0.044 Uiso 1 1 d . U . . .
O3 O 0.19705(12) 0.54731(11) 0.18458(15) 0.0501(4) Uani 1 1 d . . . . .
N1 N 1.04741(11) 0.21799(10) 0.15254(11) 0.0219(3) Uani 1 1 d . . . . .
H0 H 1.0068 0.1808 0.0958 0.026 Uiso 1 1 calc R U . . .
N2 N 0.87914(11) 0.35559(10) 0.16486(12) 0.0224(3) Uani 1 1 d . . . . .
N3 N 0.48383(11) 0.38860(9) 0.20124(11) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.94704(14) 0.35001(12) 0.07051(15) 0.0269(4) Uani 1 1 d . . . . .
H01A H 0.9553 0.4101 0.0398 0.032 Uiso 1 1 calc R U . . .
H01B H 0.9100 0.3117 0.0140 0.032 Uiso 1 1 calc R U . . .
C2 C 1.06054(14) 0.31109(12) 0.10650(15) 0.0261(4) Uani 1 1 d . . . . .
H02A H 1.1050 0.3081 0.0443 0.031 Uiso 1 1 calc R U . . .
H02B H 1.0985 0.3501 0.1618 0.031 Uiso 1 1 calc R U . . .
C3 C 0.97901(13) 0.22377(12) 0.24827(14) 0.0242(3) Uani 1 1 d . . . . .
H03A H 1.0178 0.2601 0.3058 0.029 Uiso 1 1 calc R U . . .
H03B H 0.9685 0.1633 0.2773 0.029 Uiso 1 1 calc R U . . .
C4 C 0.86722(13) 0.26596(11) 0.21460(14) 0.0234(3) Uani 1 1 d . . . . .
H04A H 0.8256 0.2264 0.1624 0.028 Uiso 1 1 calc R U . . .
H04B H 0.8257 0.2719 0.2786 0.028 Uiso 1 1 calc R U . . .
C5 C 0.68697(14) 0.55003(11) 0.10308(14) 0.0240(3) Uani 1 1 d . . . . .
H05 H 0.6902 0.6092 0.0767 0.029 Uiso 1 1 calc R U . . .
C6 C 0.78011(14) 0.49825(11) 0.11408(14) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.78104(13) 0.40651(11) 0.15100(13) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.68003(13) 0.37221(11) 0.17870(13) 0.0207(3) Uani 1 1 d . . . . .
H08 H 0.6767 0.3124 0.2030 0.025 Uiso 1 1 calc R U . . .
C9 C 0.58337(12) 0.42486(10) 0.17117(12) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.58515(13) 0.51425(11) 0.13168(13) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.48533(14) 0.56904(11) 0.11979(13) 0.0219(3) Uani 1 1 d . . . . .
C12 C 0.38853(14) 0.52812(11) 0.15746(13) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.39257(13) 0.44025(11) 0.19530(14) 0.0228(3) Uani 1 1 d . . . . .
H13 H 0.3278 0.4151 0.2182 0.027 Uiso 1 1 calc R U . . .
C14 C 0.28169(16) 0.57818(13) 0.15391(16) 0.0323(4) Uani 1 1 d . . . . .
C15 C 0.47729(13) 0.29377(11) 0.24044(14) 0.0219(3) Uani 1 1 d . . . . .
H15A H 0.4129 0.2874 0.2820 0.026 Uiso 1 1 calc R U . . .
H15B H 0.5429 0.2803 0.2894 0.026 Uiso 1 1 calc R U . . .
C16 C 0.46874(17) 0.22607(13) 0.14685(16) 0.0321(4) Uani 1 1 d . . . . .
H16A H 0.4618 0.1658 0.1756 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5343 0.2296 0.1081 0.039 Uiso 1 1 calc R U . . .
H16C H 0.4046 0.2398 0.0975 0.039 Uiso 1 1 calc R U . . .
C17 C 1.15580(14) 0.17301(13) 0.18418(15) 0.0276(4) Uani 1 1 d . . . . .
H17A H 1.1935 0.2045 0.2455 0.033 Uiso 1 1 calc R U . . .
H17B H 1.2007 0.1745 0.1232 0.033 Uiso 1 1 calc R U . . .
H17C H 1.1432 0.1110 0.2043 0.033 Uiso 1 1 calc R 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'
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'
S S 0.1246 0.1234 '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 124.70(13) . .
C2B N1B H1B 117.7 . .
C6B N1B H1B 117.7 . .
C2B N3B C4B 124.99(13) . .
C2B N3B H3B 117.5 . .
C4B N3B H3B 117.5 . .
N3B C2B N1B 116.24(13) . .
N3B C2B S 121.20(11) . .
N1B C2B S 122.55(11) . .
O1B C4B C5B 126.87(15) . .
O1B C4B N3B 116.45(13) . .
C5B C4B N3B 116.68(13) . .
C4B C5B C6B 121.41(14) . .
C4B C5B H5B 119.3 . .
C6B C5B H5B 119.3 . .
O2B C6B N1B 117.93(14) . .
O2B C6B C5B 126.23(15) . .
N1B C6B C5B 115.84(13) . .
C14 O2 H2 106.0(14) . .
C17 N1 C3 110.92(13) . .
C17 N1 C2 112.66(13) . .
C3 N1 C2 109.11(13) . .
C17 N1 H0 108.0 . .
C3 N1 H0 108.0 . .
C2 N1 H0 108.0 . .
C7 N2 C4 114.76(13) . .
C7 N2 C1 117.30(13) . .
C4 N2 C1 110.87(13) . .
C13 N3 C9 119.66(14) . .
C13 N3 C15 119.11(13) . .
C9 N3 C15 121.23(12) . .
N2 C1 C2 110.22(14) . .
N2 C1 H01A 109.6 . .
C2 C1 H01A 109.6 . .
N2 C1 H01B 109.6 . .
C2 C1 H01B 109.6 . .
H01A C1 H01B 108.1 . .
N1 C2 C1 109.40(13) . .
N1 C2 H02A 109.8 . .
C1 C2 H02A 109.8 . .
N1 C2 H02B 109.8 . .
C1 C2 H02B 109.8 . .
H02A C2 H02B 108.2 . .
N1 C3 C4 110.70(13) . .
N1 C3 H03A 109.5 . .
C4 C3 H03A 109.5 . .
N1 C3 H03B 109.5 . .
C4 C3 H03B 109.5 . .
H03A C3 H03B 108.1 . .
N2 C4 C3 111.40(13) . .
N2 C4 H04A 109.3 . .
C3 C4 H04A 109.3 . .
N2 C4 H04B 109.3 . .
C3 C4 H04B 109.3 . .
H04A C4 H04B 108.0 . .
C6 C5 C10 120.00(15) . .
C6 C5 H05 120.0 . .
C10 C5 H05 120.0 . .
C5 C6 F 118.33(15) . .
C5 C6 C7 123.21(15) . .
F C6 C7 118.41(15) . .
C8 C7 N2 121.89(15) . .
C8 C7 C6 116.07(14) . .
N2 C7 C6 121.94(14) . .
C7 C8 C9 121.94(15) . .
C7 C8 H08 119.0 . .
C9 C8 H08 119.0 . .
N3 C9 C8 120.36(14) . .
N3 C9 C10 119.33(14) . .
C8 C9 C10 120.30(14) . .
C9 C10 C5 118.44(14) . .
C9 C10 C11 121.28(14) . .
C5 C10 C11 120.29(15) . .
O1 C11 C12 123.00(15) . .
O1 C11 C10 121.43(15) . .
C12 C11 C10 115.57(14) . .
C13 C12 C11 120.03(15) . .
C13 C12 C14 118.84(16) . .
C11 C12 C14 121.11(15) . .
N3 C13 C12 123.96(15) . .
N3 C13 H13 118.0 . .
C12 C13 H13 118.0 . .
O3 C14 O2 121.62(17) . .
O3 C14 C12 124.21(18) . .
O2 C14 C12 114.17(17) . .
N3 C15 C16 112.20(14) . .
N3 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
N3 C15 H15B 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N1 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C2B 1.6860(16) .
O1B C4B 1.2736(18) .
O2B C6B 1.2406(18) .
N1B C2B 1.3488(19) .
N1B C6B 1.409(2) .
N1B H1B 0.8600 .
N3B C2B 1.3462(19) .
N3B C4B 1.401(2) .
N3B H3B 0.8600 .
C4B C5B 1.383(2) .
C5B C6B 1.409(2) .
C5B H5B 0.9300 .
F C6 1.3601(18) .
O1 C11 1.265(2) .
O2 C14 1.337(2) .
O2 H2 0.97(2) .
O3 C14 1.208(2) .
N1 C17 1.487(2) .
N1 C3 1.494(2) .
N1 C2 1.495(2) .
N1 H0 0.9800 .
N2 C7 1.399(2) .
N2 C4 1.464(2) .
N2 C1 1.476(2) .
N3 C13 1.335(2) .
N3 C9 1.394(2) .
N3 C15 1.480(2) .
C1 C2 1.514(2) .
C1 H01A 0.9700 .
C1 H01B 0.9700 .
C2 H02A 0.9700 .
C2 H02B 0.9700 .
C3 C4 1.509(2) .
C3 H03A 0.9700 .
C3 H03B 0.9700 .
C4 H04A 0.9700 .
C4 H04B 0.9700 .
C5 C6 1.355(2) .
C5 C10 1.410(2) .
C5 H05 0.9300 .
C6 C7 1.423(2) .
C7 C8 1.390(2) .
C8 C9 1.397(2) .
C8 H08 0.9300 .
C9 C10 1.402(2) .
C10 C11 1.447(2) .
C11 C12 1.427(2) .
C12 C13 1.372(2) .
C12 C14 1.483(2) .
C13 H13 0.9300 .
C15 C16 1.513(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
