#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229646.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_2229646
loop_
_publ_author_name
'Phelan, W. Adam'
'Ngu-Schwemlein, Maria'
'Fronczek, Frank R.'
'McLaughlin, Mark L.'
'Watkins, Steven F.'
_publ_section_title
;
 1,2-Dihydro-9H-carbazole-4(3H)-thione
;
_journal_coeditor_code           FL2336
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o757
_journal_paper_doi               10.1107/S1600536811006623
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H11 N S'
_chemical_formula_moiety         'C12 H11 N S'
_chemical_formula_sum            'C12 H11 N S'
_chemical_formula_weight         201.28
_chemical_melting_point          447.0(10)
_chemical_name_systematic
;
1,2-Dihydro-9H-carbazole-4(3H)-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.599(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6353(14)
_cell_length_b                   12.1395(15)
_cell_length_c                   9.5808(14)
_cell_measurement_reflns_used    3145
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      2.8
_cell_volume                     971.9(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6145
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         31.8
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0381P)²+0.4607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                2915
_reflns_number_total             3305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2336.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229646
_cod_database_fobs_code          2229646
loop_
_symmetry_equiv_pos_as_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
S S1 0.73572(3) 0.09251(2) 0.17793(3) 0.01632(8) Uani d . 1 . .
N N9 0.40190(10) 0.23264(7) 0.49231(9) 0.01459(16) Uani d . 1 . .
H H9 0.3596 0.2739 0.5486 0.018 Uiso calc R 1 . .
C C1 0.64126(13) 0.35282(8) 0.50486(11) 0.01640(19) Uani d . 1 . .
H H1A 0.6442 0.3693 0.6067 0.02 Uiso calc R 1 . .
H H1B 0.5975 0.4178 0.4456 0.02 Uiso calc R 1 . .
C C2 0.81014(12) 0.32729(9) 0.49014(11) 0.01613(19) Uani d . 1 . .
H H2A 0.8612 0.2724 0.5639 0.019 Uiso calc R 1 . .
H H2B 0.8756 0.3953 0.5072 0.019 Uiso calc R 1 . .
C C3 0.80512(12) 0.28219(8) 0.33970(11) 0.01504(18) Uani d . 1 . .
H H3A 0.766 0.3409 0.2677 0.018 Uiso calc R 1 . .
H H3B 0.9153 0.2631 0.3355 0.018 Uiso calc R 1 . .
C C4 0.69952(12) 0.18152(8) 0.29869(10) 0.01239(17) Uani d . 1 . .
C C5 0.40380(12) -0.00895(8) 0.27655(10) 0.01451(18) Uani d . 1 . .
H H5 0.4724 -0.0398 0.2234 0.017 Uiso calc R 1 . .
C C6 0.26491(13) -0.06343(9) 0.28577(11) 0.0179(2) Uani d . 1 . .
H H6 0.2394 -0.1325 0.2389 0.021 Uiso calc R 1 . .
C C7 0.16174(13) -0.01841(9) 0.36297(12) 0.0196(2) Uani d . 1 . .
H H7 0.0665 -0.0567 0.3655 0.024 Uiso calc R 1 . .
C C8 0.19647(13) 0.08102(9) 0.43570(11) 0.0181(2) Uani d . 1 . .
H H8 0.1273 0.1116 0.4885 0.022 Uiso calc R 1 . .
C C10 0.53890(12) 0.25494(8) 0.45510(10) 0.01313(17) Uani d . 1 . .
C C11 0.56930(11) 0.17216(8) 0.36283(10) 0.01191(17) Uani d . 1 . .
C C12 0.44039(11) 0.09230(8) 0.34726(10) 0.01234(17) Uani d . 1 . .
C C13 0.33703(12) 0.13394(8) 0.42784(10) 0.01382(18) Uani 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 0 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 C1 C2 . . 108.17(8) ?
C10 C1 H1A . . 110.1 ?
C2 C1 H1A . . 110.1 ?
C10 C1 H1B . . 110.1 ?
C2 C1 H1B . . 110.1 ?
H1A C1 H1B . . 108.4 ?
C1 C2 C3 . . 110.92(8) ?
C1 C2 H2A . . 109.5 ?
C3 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 108 ?
C4 C3 C2 . . 113.85(8) ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3B . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C11 C4 C3 . . 116.35(8) ?
C11 C4 S1 . . 123.85(7) ?
C3 C4 S1 . . 119.73(7) ?
C6 C5 C12 . . 118.64(9) ?
C6 C5 H5 . . 120.7 ?
C12 C5 H5 . . 120.7 ?
C5 C6 C7 . . 121.32(10) ?
C5 C6 H6 . . 119.3 ?
C7 C6 H6 . . 119.3 ?
C8 C7 C6 . . 121.15(10) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C13 . . 117.08(10) ?
C7 C8 H8 . . 121.5 ?
C13 C8 H8 . . 121.5 ?
N9 C10 C11 . . 109.79(9) ?
N9 C10 C1 . . 124.55(9) ?
C11 C10 C1 . . 125.66(9) ?
C10 C11 C4 . . 120.68(9) ?
C10 C11 C12 . . 106.34(8) ?
C4 C11 C12 . . 132.83(9) ?
C5 C12 C13 . . 118.80(9) ?
C5 C12 C11 . . 135.05(9) ?
C13 C12 C11 . . 106.14(8) ?
C8 C13 N9 . . 128.98(9) ?
C8 C13 C12 . . 122.96(10) ?
N9 C13 C12 . . 108.06(8) ?
C10 N9 C13 . . 109.64(8) ?
C10 N9 H9 . . 125.2 ?
C13 N9 H9 . . 125.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C10 . 1.4860(14) ?
C1 C2 . 1.5318(14) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.5322(14) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.5162(14) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C11 . 1.4154(13) ?
C4 S1 . 1.6692(10) ?
C5 C6 . 1.3917(14) ?
C5 C12 . 1.4006(13) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4042(16) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3882(16) ?
C7 H7 . 0.95 ?
C8 C13 . 1.3920(14) ?
C8 H8 . 0.95 ?
C10 N9 . 1.3463(12) ?
C10 C11 . 1.4061(13) ?
C11 C12 . 1.4553(13) ?
C12 C13 . 1.4127(13) ?
C13 N9 . 1.3988(13) ?
N9 H9 . 0.88 ?
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 H9 S1 4_566 0.88 2.45 3.3187(9) 172
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . 49.84(11) ?
C1 C2 C3 C4 . . . . -55.67(11) ?
C2 C3 C4 C11 . . . . 28.23(12) ?
C2 C3 C4 S1 . . . . -154.52(8) ?
C12 C5 C6 C7 . . . . 0.52(15) ?
C5 C6 C7 C8 . . . . -1.47(16) ?
C6 C7 C8 C13 . . . . 0.35(15) ?
C2 C1 C10 N9 . . . . 158.35(9) ?
C2 C1 C10 C11 . . . . -21.72(13) ?
N9 C10 C11 C4 . . . . 174.61(9) ?
C1 C10 C11 C4 . . . . -5.33(15) ?
N9 C10 C11 C12 . . . . -1.56(11) ?
C1 C10 C11 C12 . . . . 178.50(9) ?
C3 C4 C11 C10 . . . . 2.22(13) ?
S1 C4 C11 C10 . . . . -174.91(7) ?
C3 C4 C11 C12 . . . . 177.20(10) ?
S1 C4 C11 C12 . . . . 0.08(16) ?
C6 C5 C12 C13 . . . . 1.45(14) ?
C6 C5 C12 C11 . . . . -179.79(10) ?
C10 C11 C12 C5 . . . . -177.03(10) ?
C4 C11 C12 C5 . . . . 7.46(19) ?
C10 C11 C12 C13 . . . . 1.84(10) ?
C4 C11 C12 C13 . . . . -173.67(10) ?
C7 C8 C13 N9 . . . . -178.60(10) ?
C7 C8 C13 C12 . . . . 1.70(15) ?
C5 C12 C13 C8 . . . . -2.64(14) ?
C11 C12 C13 C8 . . . . 178.27(9) ?
C5 C12 C13 N9 . . . . 177.61(8) ?
C11 C12 C13 N9 . . . . -1.47(10) ?
C11 C10 N9 C13 . . . . 0.66(11) ?
C1 C10 N9 C13 . . . . -179.40(9) ?
C8 C13 N9 C10 . . . . -179.18(10) ?
C12 C13 N9 C10 . . . . 0.55(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656578
