#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239846.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239846
loop_
_publ_author_name
'Shishkina, Svitlana V.'
'Kucher, Olexandr V.'
'Kolodiazhnaya, Anastasiya O.'
'Smolii, Oleg B.'
'Tolmachev, Andrey A.'
_publ_section_title
;
 Crystal structure of
 (S)-1-(1,3-benzothiazol-2-yl)-2,2,2-trifluoroethanol
;
_journal_coeditor_code           LH5717
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o946
_journal_paper_doi               10.1107/S1600536814016547
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H6 F3 N O S'
_chemical_formula_moiety         'C9 H6 F3 N O S'
_chemical_formula_sum            'C9 H6 F3 N O S'
_chemical_formula_weight         233.21
_chemical_name_systematic
;
(S)-1-(1,3-Benzothiazol-2-yl)-2,2,2-trifluoroethanol
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.411(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2116(9)
_cell_length_b                   5.5052(4)
_cell_length_c                   10.2279(8)
_cell_measurement_reflns_used    1591
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      3.5
_cell_volume                     494.91(8)
_computing_cell_refinement
;
CrysAlis CCD (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis CCD (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis RED (Agilent, 2012)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Agilent Xcalibur3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4650
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details 'Flack (1983), 1199 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0417
_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)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2293
_reflns_number_total             2768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5717sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        494.91(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2239846
_cod_database_fobs_code          2239846
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F1 0.84725(19) 0.5557(5) 0.85264(17) 0.0991(7) Uani d D 1 1
F F2 0.89881(19) 0.5084(6) 1.06943(16) 0.1122(8) Uani d D 1 1
F F3 0.7640(2) 0.2434(2) 0.9323(2) 0.0913(6) Uani d D 1 1
S S1 0.51635(7) 0.81353(17) 0.68465(5) 0.05600(17) Uani d . 1 1
N N1 0.4284(2) 0.4285(3) 0.78357(16) 0.0454(4) Uani d . 1 1
O O1 0.5967(2) 0.5338(3) 1.05476(15) 0.0604(4) Uani d . 1 1
H H1O 0.582(4) 0.637(7) 1.110(3) 0.088(11) Uiso d . 1 1
C C1 0.3304(2) 0.4556(4) 0.65070(19) 0.0434(4) Uani d . 1 1
C C2 0.2101(3) 0.3050(6) 0.5878(2) 0.0579(5) Uani d . 1 1
H H2 0.189(3) 0.176(5) 0.643(2) 0.046(6) Uiso d . 1 1
C C3 0.1234(3) 0.3593(6) 0.4559(3) 0.0651(7) Uani d . 1 1
H H3 0.050(4) 0.253(7) 0.424(3) 0.089(11) Uiso d . 1 1
C C4 0.1525(3) 0.5594(6) 0.3878(2) 0.0634(7) Uani d . 1 1
H H4 0.093(3) 0.582(6) 0.293(3) 0.067(8) Uiso d . 1 1
C C5 0.2713(3) 0.7138(5) 0.4479(2) 0.0569(6) Uani d . 1 1
H H5 0.299(3) 0.864(7) 0.408(3) 0.072(9) Uiso d . 1 1
C C6 0.3606(3) 0.6586(4) 0.5814(2) 0.0463(5) Uani d . 1 1
C C7 0.5280(3) 0.6011(4) 0.81243(18) 0.0440(4) Uani d . 1 1
C C8 0.6483(3) 0.6243(5) 0.9503(2) 0.0511(5) Uani d . 1 1
H H8 0.689(2) 0.799(5) 0.976(2) 0.044(5) Uiso d . 1 1
C C9 0.7885(2) 0.4822(3) 0.95081(14) 0.0689(8) Uani d D 1 1
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
C6 S1 C7 88.89(10)
C7 N1 C1 110.59(17)
C8 O1 H1O 116(3)
C2 C1 C6 119.94(19)
C2 C1 N1 125.8(2)
C6 C1 N1 114.27(18)
C1 C2 C3 118.3(3)
C1 C2 H2 116.4(13)
C3 C2 H2 125.0(14)
C4 C3 C2 121.8(3)
C4 C3 H3 126(2)
C2 C3 H3 112(2)
C3 C4 C5 121.3(2)
C3 C4 H4 118.2(19)
C5 C4 H4 120.3(18)
C4 C5 C6 117.2(2)
C4 C5 H5 127.0(15)
C6 C5 H5 115.7(16)
C1 C6 C5 121.4(2)
C1 C6 S1 109.85(15)
C5 C6 S1 128.7(2)
N1 C7 C8 123.09(18)
N1 C7 S1 116.39(14)
C8 C7 S1 120.51(17)
O1 C8 C9 107.55(18)
O1 C8 C7 111.31(19)
C9 C8 C7 110.22(16)
O1 C8 H8 108.9(11)
C9 C8 H8 103.3(13)
C7 C8 H8 115.0(12)
F2 C9 F3 106.5(2)
F2 C9 F1 106.24(18)
F3 C9 F1 106.3(2)
F2 C9 C8 111.38(19)
F3 C9 C8 113.65(17)
F1 C9 C8 112.25(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.3382(10)
F2 C9 1.3372(10)
F3 C9 1.3376(10)
S1 C6 1.731(2)
S1 C7 1.733(2)
N1 C7 1.292(3)
N1 C1 1.396(2)
O1 C8 1.385(3)
O1 H1O 0.84(4)
C1 C2 1.379(3)
C1 C6 1.395(3)
C2 C3 1.379(3)
C2 H2 0.96(3)
C3 C4 1.372(4)
C3 H3 0.88(4)
C4 C5 1.377(4)
C4 H4 0.96(3)
C5 C6 1.400(3)
C5 H5 0.99(4)
C7 C8 1.516(3)
C8 C9 1.509(3)
C8 H8 1.04(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O N1 2_657 0.84(4) 1.96(4) 2.781(2) 166(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
C7 N1 C1 C2 -179.2(2)
C7 N1 C1 C6 -0.5(3)
C6 C1 C2 C3 0.8(4)
N1 C1 C2 C3 179.4(2)
C1 C2 C3 C4 -1.1(4)
C2 C3 C4 C5 0.9(4)
C3 C4 C5 C6 -0.3(4)
C2 C1 C6 C5 -0.2(3)
N1 C1 C6 C5 -179.1(2)
C2 C1 C6 S1 179.74(19)
N1 C1 C6 S1 0.9(2)
C4 C5 C6 C1 0.0(4)
C4 C5 C6 S1 -180.0(2)
C7 S1 C6 C1 -0.83(16)
C7 S1 C6 C5 179.1(2)
C1 N1 C7 C8 178.7(2)
C1 N1 C7 S1 -0.2(2)
C6 S1 C7 N1 0.62(18)
C6 S1 C7 C8 -178.34(19)
N1 C7 C8 O1 -30.8(3)
S1 C7 C8 O1 148.13(17)
N1 C7 C8 C9 88.5(3)
S1 C7 C8 C9 -92.6(2)
O1 C8 C9 F2 -61.2(2)
C7 C8 C9 F2 177.3(2)
O1 C8 C9 F3 59.1(2)
C7 C8 C9 F3 -62.4(2)
O1 C8 C9 F1 179.82(18)
C7 C8 C9 F1 58.3(2)
