#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/56/1505671.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_1505671
loop_
_publ_author_name
'Hashimoto, Akihiro'
'Pais, Godwin C. G.'
'Wang, Qiuping'
'Lucien, Edlaine'
'Incarvito, Christopher D.'
'Deshpande, Milind'
'Bradbury, Barton J.'
'Wiles, Jason A.'
_publ_section_title
;
 Practical Synthesis and Molecular Structure of a Potent Broad-Spectrum
 Antibacterial Isothiazoloquinolone
;
_journal_issue                   3
_journal_name_full               'Organic Process Research & Development'
_journal_page_first              389
_journal_paper_doi               10.1021/op700014t
_journal_volume                  11
_journal_year                    2007
_chemical_formula_sum            'C16 H15 F2 N O4 S'
_chemical_formula_weight         355.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.76(3)
_cell_angle_beta                 99.69(3)
_cell_angle_gamma                113.51(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8361(18)
_cell_length_b                   9.6639(19)
_cell_length_c                   10.439(2)
_cell_measurement_temperature    173(2)
_cell_volume                     768.7(4)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_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      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6440
_diffrn_reflns_theta_full        29.03
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                3056
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op700014t-file002.cif
_cod_data_source_block           jw06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        768.7(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505671
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.28115(6) 0.29480(5) 0.68907(4) 0.03735(17) Uani 1 1 d .
F1 F 0.86887(15) 0.44404(16) 1.13586(12) 0.0571(4) Uani 1 1 d .
F2 F 0.57681(18) 0.18180(14) 1.07970(11) 0.0591(4) Uani 1 1 d .
O1 O 0.79185(15) 0.70382(15) 0.78861(13) 0.0399(3) Uani 1 1 d .
O2 O 0.41429(16) 0.71366(15) 0.51397(12) 0.0401(3) Uani 1 1 d .
O3 O 0.64056(16) 0.86294(14) 0.69474(12) 0.0385(3) Uani 1 1 d .
O4 O 0.2992(2) 0.10923(18) 0.85207(15) 0.0784(6) Uani 1 1 d .
N1 N 0.20407(19) 0.44107(18) 0.53141(14) 0.0333(3) Uani 1 1 d .
H1 H 0.225(3) 0.513(3) 0.496(2) 0.050(6) Uiso 1 1 d .
C1 C 0.4977(2) 0.58991(19) 0.67095(15) 0.0290(3) Uani 1 1 d .
C2 C 0.6445(2) 0.60105(19) 0.76660(16) 0.0310(4) Uani 1 1 d .
C3 C 0.6182(2) 0.4847(2) 0.84566(16) 0.0315(4) Uani 1 1 d .
C4 C 0.7576(2) 0.5171(2) 0.95417(18) 0.0372(4) Uani 1 1 d .
H4A H 0.8641 0.6081 0.9739 0.045 Uiso 1 1 calc R
C5 C 0.7369(3) 0.4151(2) 1.03072(18) 0.0414(4) Uani 1 1 d .
C6 C 0.5853(3) 0.2796(2) 1.00294(18) 0.0430(5) Uani 1 1 d .
C7 C 0.4467(3) 0.2440(2) 0.89596(18) 0.0432(5) Uani 1 1 d .
C8 C 0.4649(2) 0.3502(2) 0.81902(16) 0.0338(4) Uani 1 1 d .
C9 C 0.3364(2) 0.45772(19) 0.62693(15) 0.0297(3) Uani 1 1 d .
C10 C 0.5127(2) 0.7235(2) 0.61687(16) 0.0308(3) Uani 1 1 d .
C11 C 0.6479(3) 1.0003(2) 0.6546(2) 0.0461(5) Uani 1 1 d .
H11A H 0.5409 1.0104 0.6559 0.055 Uiso 1 1 calc R
H11B H 0.6611 0.9900 0.5613 0.055 Uiso 1 1 calc R
C12 C 0.7995(3) 1.1425(2) 0.7545(2) 0.0535(5) Uani 1 1 d .
H12A H 0.8080 1.2378 0.7306 0.080 Uiso 1 1 calc R
H12B H 0.9045 1.1315 0.7518 0.080 Uiso 1 1 calc R
H12C H 0.7850 1.1512 0.8464 0.080 Uiso 1 1 calc R
C13 C 0.2123(3) 0.0434(3) 0.9424(2) 0.0541(5) Uani 1 1 d .
H13A H 0.1077 -0.0537 0.8904 0.081 Uiso 1 1 calc R
H13B H 0.1814 0.1194 0.9949 0.081 Uiso 1 1 calc R
H13C H 0.2871 0.0188 1.0046 0.081 Uiso 1 1 calc R
C14 C 0.0313(2) 0.3211(2) 0.50205(17) 0.0352(4) Uani 1 1 d .
H14A H -0.0265 0.3282 0.5760 0.042 Uiso 1 1 calc R
C15 C -0.0190(2) 0.1573(2) 0.41415(17) 0.0378(4) Uani 1 1 d .
H15A H 0.0702 0.1373 0.3793 0.045 Uiso 1 1 calc R
H15B H -0.1032 0.0670 0.4354 0.045 Uiso 1 1 calc R
C16 C -0.0815(2) 0.2625(2) 0.35956(18) 0.0376(4) Uani 1 1 d .
H16A H -0.0309 0.3071 0.2909 0.045 Uiso 1 1 calc R
H16B H -0.2042 0.2369 0.3470 0.045 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'
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
C8 S1 C9 102.68(9)
C10 O3 C11 116.14(14)
C7 O4 C13 122.13(16)
H1 N1 C9 114.7(15)
H1 N1 C14 120.5(15)
C9 N1 C14 124.26(14)
C9 C1 C2 123.26(15)
C9 C1 C10 116.59(14)
C2 C1 C10 120.15(15)
O1 C2 C1 123.36(15)
O1 C2 C3 117.26(15)
C1 C2 C3 119.37(15)
C8 C3 C4 119.11(16)
C8 C3 C2 123.76(15)
C4 C3 C2 117.11(16)
C5 C4 C3 118.75(18)
F1 C5 C4 119.83(18)
F1 C5 C6 117.92(17)
C4 C5 C6 122.24(17)
F2 C6 C5 118.80(17)
F2 C6 C7 120.96(18)
C5 C6 C7 120.22(17)
O4 C7 C6 125.27(17)
O4 C7 C8 116.49(16)
C6 C7 C8 118.03(17)
C3 C8 C7 121.62(16)
C3 C8 S1 124.45(13)
C7 C8 S1 113.93(14)
N1 C9 C1 123.77(15)
N1 C9 S1 111.18(12)
C1 C9 S1 125.05(12)
O2 C10 O3 120.92(15)
O2 C10 C1 124.87(16)
O3 C10 C1 114.12(14)
O3 C11 C12 107.31(16)
N1 C14 C16 118.07(15)
N1 C14 C15 119.24(15)
C16 C14 C15 59.94(12)
C16 C15 C14 59.78(12)
C14 C16 C15 60.28(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.7413(19)
S1 C9 1.7458(17)
F1 C5 1.351(2)
F2 C6 1.347(2)
O1 C2 1.228(2)
O2 C10 1.2233(19)
O3 C10 1.335(2)
O3 C11 1.452(2)
O4 C7 1.344(2)
O4 C13 1.408(3)
N1 H1 0.82(2)
N1 C9 1.334(2)
N1 C14 1.433(2)
C1 C9 1.401(2)
C1 C2 1.449(2)
C1 C10 1.480(2)
C2 C3 1.495(2)
C3 C8 1.386(3)
C3 C4 1.406(2)
C4 C5 1.367(3)
C5 C6 1.382(3)
C6 C7 1.382(3)
C7 C8 1.405(2)
C11 C12 1.499(3)
C14 C16 1.495(2)
C14 C15 1.502(3)
C15 C16 1.497(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 28293081 ChemSpider
