#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:07:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179652 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/05/4510573.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_4510573
loop_
_publ_author_name
'Eccles, Kevin S.'
'Morrison, Robin E.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Crystal Landscape of Primary Aromatic Thioamides
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2753
_journal_paper_doi               10.1021/cg401891f
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C7 H6 F N S'
_chemical_formula_sum            'C7 H6 F N S'
_chemical_formula_weight         155.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.070(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.9388(16)
_cell_length_b                   18.040(4)
_cell_length_c                   14.087(4)
_cell_measurement_reflns_used    4548
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      24.1581
_cell_measurement_theta_min      2.6936
_cell_volume                     1486.0(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 3, 0, 0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16359
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.529
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.9807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1291
_reflns_number_gt                1967
_reflns_number_total             2605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401891f_si_002.cif
_cod_data_source_block           Compound_04
_cod_depositor_comments
'Adding full bibliography for 4510565--4510578.cif.'
_cod_original_cell_volume        1486.0(6)
_cod_database_code               4510573
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.6353(5) 0.18307(14) 0.87810(18) 0.0502(6) Uani d . 1 C .
C C2 0.7994(5) 0.23191(17) 0.8563(2) 0.0649(8) Uani d . 1 . .
H H2B 0.9391 0.2347 0.898 0.078 Uiso calc PR 0.12 A 2
C C3 0.7648(7) 0.2765(2) 0.7757(3) 0.0827(10) Uani d . 1 C .
H H3 0.8779 0.3092 0.764 0.099 Uiso calc R 1 . .
C C4 0.5612(8) 0.2719(2) 0.7131(3) 0.0861(11) Uani d . 1 . .
H H4 0.5364 0.3012 0.6579 0.103 Uiso calc R 1 C .
C C5 0.3943(7) 0.2247(2) 0.7313(2) 0.0805(10) Uani d . 1 C .
H H5 0.2564 0.2217 0.6884 0.097 Uiso calc R 1 . .
C C6 0.4302(5) 0.18147(17) 0.8131(2) 0.0635(8) Uani d . 1 . .
H H6A 0.3138 0.1503 0.8252 0.076 Uiso calc PR 0.88 B 1
C C7 0.6699(5) 0.13595(15) 0.9664(2) 0.0543(7) Uani d . 1 . .
S S8 0.46251(16) 0.12262(8) 1.02910(9) 0.1126(5) Uani d . 1 C .
N N9 0.8749(5) 0.10742(19) 0.9934(2) 0.0740(8) Uani d . 1 C .
C C11 0.9175(4) 0.94783(14) 0.34908(18) 0.0476(6) Uani d . 1 . .
C C12 0.7817(5) 0.94874(16) 0.4199(2) 0.0584(7) Uani d . 1 . .
C C13 0.8269(6) 0.9070(2) 0.5030(2) 0.0732(9) Uani d . 1 . .
H H13 0.7331 0.9101 0.5492 0.088 Uiso calc R 1 . .
F F10A 0.9981(4) 0.24015(13) 0.91701(17) 0.0919(7) Uani d P 0.88 C 1
F F10B 0.253(3) 0.1439(10) 0.8390(11) 0.084(4) Uani d P 0.12 C 2
C C14 1.0124(6) 0.86100(19) 0.5158(2) 0.0776(10) Uani d . 1 . .
H H14 1.0456 0.8324 0.5714 0.093 Uiso calc R 1 . .
C C15 1.1509(6) 0.85658(18) 0.4469(2) 0.0737(9) Uani d . 1 . .
H H15 1.2754 0.8245 0.4556 0.088 Uiso calc R 1 . .
C C16 1.1046(5) 0.89977(16) 0.3650(2) 0.0593(7) Uani d . 1 . .
H H16 1.2 0.8968 0.3193 0.071 Uiso calc R 1 . .
C C17 0.8731(4) 0.99370(14) 0.26006(19) 0.0488(6) Uani d . 1 . .
S S18 1.08293(12) 1.01378(5) 0.19935(6) 0.0689(3) Uani d . 1 . .
N N19 0.6630(4) 1.01711(17) 0.2288(2) 0.0720(8) Uani d D 1 . .
F F20 0.5966(3) 0.99441(12) 0.40957(13) 0.0858(6) Uani d . 1 . .
H H19A 0.633(6) 1.0441(16) 0.1768(17) 0.081(11) Uiso d D 1 . .
H H19B 0.553(5) 1.0045(18) 0.257(2) 0.088(12) Uiso d D 1 . .
H H9A 0.900(5) 0.0783(19) 1.043(3) 0.074(10) Uiso d . 1 . .
H H9B 0.980(7) 0.115(2) 0.961(3) 0.110(15) Uiso d . 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
C2 C1 C6 115.8(3)
C2 C1 C7 123.2(3)
C6 C1 C7 121.0(3)
F10A C2 C3 116.7(3)
F10A C2 C1 120.2(3)
C3 C2 C1 122.9(3)
C4 C3 C2 118.9(3)
C5 C4 C3 120.4(3)
C4 C5 C6 119.9(3)
F10B C6 C5 119.7(7)
F10B C6 C1 117.7(7)
C5 C6 C1 122.0(3)
N9 C7 C1 116.8(3)
N9 C7 S8 121.8(2)
C1 C7 S8 121.4(2)
C12 C11 C16 116.0(2)
C12 C11 C17 124.1(2)
C16 C11 C17 120.0(2)
F20 C12 C13 117.1(3)
F20 C12 C11 119.4(3)
C13 C12 C11 123.5(3)
C14 C13 C12 118.5(3)
C13 C14 C15 120.5(3)
C16 C15 C14 119.9(3)
C15 C16 C11 121.5(3)
N19 C17 C11 118.5(2)
N19 C17 S18 120.5(2)
C11 C17 S18 120.98(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(4)
C1 C6 1.391(4)
C1 C7 1.491(4)
C2 F10A 1.339(4)
C2 C3 1.377(5)
C3 C4 1.369(5)
C4 C5 1.365(5)
C5 C6 1.377(4)
C6 F10B 1.354(17)
C7 N9 1.315(4)
C7 S8 1.654(3)
C11 C12 1.388(4)
C11 C16 1.396(4)
C11 C17 1.487(4)
C12 F20 1.361(3)
C12 C13 1.378(4)
C13 C14 1.366(5)
C14 C15 1.381(5)
C15 C16 1.379(4)
C17 N19 1.318(3)
C17 S18 1.670(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
N9 H9B F10A . 0.85(4) 2.34(4) 2.776(4) 112.(3)
N9 H9B F10B 1_655 0.85(4) 2.61(5) 3.452(18) 172.(4)
N9 H9B S8 1_655 0.85(4) 2.86(4) 3.449(3) 128.(3)
N9 H9A S18 1_546 0.87(3) 2.56(4) 3.397(3) 163.(3)
N19 H19A S8 1_564 0.871(18) 2.57(2) 3.433(3) 169.(3)
N19 H19B F20 . 0.850(18) 2.13(3) 2.676(3) 122.(3)
N19 H19B S18 1_455 0.850(18) 2.78(3) 3.397(3) 131.(3)
