#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/57/2105731.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_2105731
loop_
_publ_author_name
'Surov, Artem O.'
'Proshin, Alexey N.'
'Perlovich, German L.'
_publ_section_title
;
 Crystal structure analysis and sublimation thermodynamics of bicyclo
 derivatives of a neuroprotector family
;
_journal_coeditor_code           BI5003
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              47
_journal_page_last               53
_journal_paper_doi               10.1107/S2052520613024384
_journal_volume                  70
_journal_year                    2014
_chemical_formula_moiety         'C14 H15 F3 N2 S'
_chemical_formula_sum            'C14 H15 F3 N2 S'
_chemical_formula_weight         300.34
_chemical_melting_point          364
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.33(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.074(8)
_cell_length_b                   9.185(5)
_cell_length_c                   12.652(8)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      5
_cell_volume                     1433.7(16)
_computing_cell_refinement       CAD-4
_computing_data_collection       'CAD-4 (Enraf-Nonius, 1993)'
_computing_data_reduction        CAD-4
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       'ω-\2q 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  0.0595
_diffrn_reflns_av_sigmaI/netI    0.1951
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2627
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.351
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.875
_refine_ls_R_factor_all          0.2773
_refine_ls_R_factor_gt           0.0745
_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)+(0.1222P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2209
_reflns_number_gt                852
_reflns_number_total             2514
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi5003sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        1433.7(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2105731
_cod_database_fobs_code          2105731
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 0.56653(12) 0.3174(2) 0.51108(15) 0.0775(7) Uani d . 1 1
F F1 0.0434(16) 0.166(2) 0.573(3) 0.103(9) Uani d PD 0.46(5) 1
F F2 0.0584(12) 0.294(4) 0.4449(11) 0.135(10) Uani d PD 0.46(5) 1
F F3 0.0797(18) 0.385(3) 0.601(3) 0.185(16) Uani d PD 0.46(5) 1
F F1' 0.0448(14) 0.1507(13) 0.521(4) 0.131(9) Uani d PD 0.54(5) 1
F F2' 0.0591(15) 0.364(4) 0.475(3) 0.242(19) Uani d PD 0.54(5) 1
F F3' 0.0757(15) 0.313(6) 0.6401(19) 0.253(15) Uani d PD 0.54(5) 1
N N1 0.5501(3) 0.1450(6) 0.6764(4) 0.0659(15) Uani d . 1 1
N N2 0.7223(3) 0.1656(5) 0.6649(4) 0.0545(13) Uani d . 1 1
C C1 0.2181(4) 0.2400(7) 0.5837(6) 0.0640(18) Uani d . 1 1
C C2 0.2573(5) 0.1588(8) 0.5137(6) 0.079(2) Uani d . 1 1
H H2A 0.2096 0.1230 0.4468 0.095 Uiso calc R 1 1
C C3 0.3679(5) 0.1299(7) 0.5423(6) 0.073(2) Uani d . 1 1
H H3A 0.3934 0.0764 0.4938 0.087 Uiso calc R 1 1
C C4 0.4405(4) 0.1803(7) 0.6430(5) 0.0588(16) Uani d . 1 1
C C5 0.4002(4) 0.2656(8) 0.7123(5) 0.0679(19) Uani d . 1 1
H H5A 0.4473 0.3032 0.7789 0.081 Uiso calc R 1 1
C C6 0.2914(5) 0.2936(8) 0.6819(6) 0.073(2) Uani d . 1 1
H H6A 0.2660 0.3504 0.7287 0.088 Uiso calc R 1 1
C C7 0.0983(5) 0.2706(7) 0.5522(7) 0.088(2) Uani d D 1 1
C C8 0.6124(4) 0.2024(6) 0.6246(5) 0.0527(15) Uani d . 1 1
C C9 0.7849(4) 0.2160(7) 0.5920(5) 0.0662(18) Uani d . 1 1
H H9A 0.8569 0.1736 0.6178 0.079 Uiso calc R 1 1
H H9B 0.7488 0.1840 0.5156 0.079 Uiso calc R 1 1
C C10 0.7931(4) 0.3754(7) 0.5951(6) 0.0636(17) Uani d . 1 1
H H10A 0.8388 0.4045 0.5510 0.076 Uiso calc R 1 1
C C11 0.6792(5) 0.4441(8) 0.5405(6) 0.076(2) Uani d . 1 1
H H11A 0.6771 0.4904 0.4709 0.091 Uiso calc R 1 1
H H11B 0.6693 0.5196 0.5898 0.091 Uiso calc R 1 1
C C12 0.7783(4) 0.2044(8) 0.7815(5) 0.0683(19) Uani d . 1 1
H H12A 0.8485 0.1569 0.8072 0.082 Uiso calc R 1 1
H H12B 0.7366 0.1699 0.8273 0.082 Uiso calc R 1 1
C C13 0.7935(5) 0.3649(8) 0.7956(5) 0.075(2) Uani d . 1 1
H H13A 0.8387 0.3863 0.8718 0.090 Uiso calc R 1 1
H H13B 0.7237 0.4112 0.7825 0.090 Uiso calc R 1 1
C C14 0.8467(5) 0.4272(8) 0.7135(6) 0.073(2) Uani d . 1 1
H H14A 0.8434 0.5327 0.7150 0.088 Uiso calc R 1 1
H H14B 0.9225 0.3992 0.7382 0.088 Uiso calc R 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'
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 C11 100.8(3)
C8 N1 C4 120.1(5)
C8 N2 C12 114.9(4)
C8 N2 C9 114.0(5)
C12 N2 C9 110.8(4)
C2 C1 C6 118.3(5)
C2 C1 C7 120.4(6)
C6 C1 C7 121.4(6)
C1 C2 C3 120.7(6)
C1 C2 H2A 119.7
C3 C2 H2A 119.7
C4 C3 C2 120.6(6)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
N1 C4 C3 121.5(6)
N1 C4 C5 120.1(6)
C3 C4 C5 118.3(5)
C6 C5 C4 120.0(6)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C1 122.1(6)
C5 C6 H6A 118.9
C1 C6 H6A 118.9
F1 C7 F3 107.9(9)
F1 C7 F2 106.5(9)
F3 C7 F2 106.8(10)
F2' C7 F1' 107.7(9)
F2' C7 F3' 107.6(9)
F1' C7 F3' 105.0(9)
F2' C7 C1 116.7(10)
F1 C7 C1 114.2(11)
F3 C7 C1 111.8(12)
F1' C7 C1 109.3(10)
F3' C7 C1 109.9(10)
F2 C7 C1 109.2(9)
N1 C8 N2 117.0(5)
N1 C8 S1 124.0(4)
N2 C8 S1 118.9(4)
C10 C9 N2 110.0(5)
C10 C9 H9A 109.7
N2 C9 H9A 109.7
C10 C9 H9B 109.7
N2 C9 H9B 109.7
H9A C9 H9B 108.2
C9 C10 C14 110.4(6)
C9 C10 C11 110.0(5)
C14 C10 C11 112.1(5)
C9 C10 H10A 108.1
C14 C10 H10A 108.1
C11 C10 H10A 108.1
C10 C11 S1 115.1(5)
C10 C11 H11A 108.5
S1 C11 H11A 108.5
C10 C11 H11B 108.5
S1 C11 H11B 108.5
H11A C11 H11B 107.5
N2 C12 C13 111.4(5)
N2 C12 H12A 109.3
C13 C12 H12A 109.3
N2 C12 H12B 109.3
C13 C12 H12B 109.3
H12A C12 H12B 108.0
C12 C13 C14 111.1(5)
C12 C13 H13A 109.4
C14 C13 H13A 109.4
C12 C13 H13B 109.4
C14 C13 H13B 109.4
H13A C13 H13B 108.0
C10 C14 C13 112.8(5)
C10 C14 H14A 109.0
C13 C14 H14A 109.0
C10 C14 H14B 109.0
C13 C14 H14B 109.0
H14A C14 H14B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.723(6)
S1 C11 1.817(6)
F1 C7 1.281(10)
F2 C7 1.302(10)
F3 C7 1.282(11)
F1' C7 1.295(10)
F2' C7 1.271(10)
F3' C7 1.300(10)
N1 C8 1.313(7)
N1 C4 1.391(7)
N2 C8 1.398(6)
N2 C12 1.458(7)
N2 C9 1.494(7)
C1 C2 1.380(9)
C1 C6 1.385(9)
C1 C7 1.509(8)
C2 C3 1.395(8)
C2 H2A 0.9300
C3 C4 1.392(8)
C3 H3A 0.9300
C4 C5 1.402(8)
C5 C6 1.369(7)
C5 H5A 0.9300
C6 H6A 0.9300
C9 C10 1.468(9)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C14 1.505(8)
C10 C11 1.553(8)
C10 H10A 0.9800
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.490(9)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.538(8)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
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
C6 C1 C2 C3 1.0(10)
C7 C1 C2 C3 -179.9(6)
C1 C2 C3 C4 1.1(11)
C8 N1 C4 C3 71.2(8)
C8 N1 C4 C5 -110.3(7)
C2 C3 C4 N1 175.9(6)
C2 C3 C4 C5 -2.6(10)
N1 C4 C5 C6 -176.5(6)
C3 C4 C5 C6 2.0(9)
C4 C5 C6 C1 0.1(10)
C2 C1 C6 C5 -1.5(10)
C7 C1 C6 C5 179.3(6)
C2 C1 C7 F2' -74(3)
C6 C1 C7 F2' 105(2)
C2 C1 C7 F1 80.8(19)
C6 C1 C7 F1 -100.1(18)
C2 C1 C7 F3 -156(2)
C6 C1 C7 F3 23(2)
C2 C1 C7 F1' 48(2)
C6 C1 C7 F1' -133(2)
C2 C1 C7 F3' 163(3)
C6 C1 C7 F3' -18(3)
C2 C1 C7 F2 -38(2)
C6 C1 C7 F2 140.8(18)
C4 N1 C8 N2 178.1(5)
C4 N1 C8 S1 -2.4(8)
C12 N2 C8 N1 -59.3(7)
C9 N2 C8 N1 171.2(5)
C12 N2 C8 S1 121.1(5)
C9 N2 C8 S1 -8.4(7)
C11 S1 C8 N1 142.4(5)
C11 S1 C8 N2 -38.1(5)
C8 N2 C9 C10 68.6(7)
C12 N2 C9 C10 -62.9(7)
N2 C9 C10 C14 58.0(6)
N2 C9 C10 C11 -66.2(7)
C9 C10 C11 S1 10.4(7)
C14 C10 C11 S1 -112.8(6)
C8 S1 C11 C10 36.3(5)
C8 N2 C12 C13 -71.5(6)
C9 N2 C12 C13 59.6(6)
N2 C12 C13 C14 -51.9(6)
C9 C10 C14 C13 -51.8(7)
C11 C10 C14 C13 71.2(7)
C12 C13 C14 C10 48.4(8)
