#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230883.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_2230883
loop_
_publ_author_name
'Archana, R.'
'Prabakaran, K.'
'Rajendra Prasad, K. J.'
'Thiruvalluvar, A.'
'Butcher, R. J.'
_publ_section_title
;
 6-Methyl-2,3,4,9-tetrahydro-1H-carbazole-1-thione
;
_journal_coeditor_code           TK2746
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1642
_journal_paper_doi               10.1107/S1600536811019246
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H13 N S'
_chemical_formula_moiety         'C13 H13 N S'
_chemical_formula_structural     'C13 H13 N S'
_chemical_formula_sum            'C13 H13 N S'
_chemical_formula_weight         215.31
_chemical_melting_point          356
_chemical_name_common            carbazole
_chemical_name_systematic
;
6-Methyl-2,3,4,9-tetrahydro-1H-carbazole-1-thione
;
_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
_cell_angle_alpha                115.009(7)
_cell_angle_beta                 104.901(6)
_cell_angle_gamma                98.074(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0846(4)
_cell_length_b                   9.5287(7)
_cell_length_c                   9.6384(6)
_cell_measurement_reflns_used    2595
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      72.6139
_cell_measurement_theta_min      5.3389
_cell_volume                     546.28(8)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3471
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         72.77
_diffrn_reflns_theta_min         5.34
_exptl_absorpt_coefficient_mu    2.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0834P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                1924
_reflns_number_total             2102
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2746.cif
_cod_data_source_block           I
_cod_database_code               2230883
_cod_database_fobs_code          2230883
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.12016(7) 0.28362(5) 0.07548(6) 0.05670(10) Uani d . 1.000 A .
N N9 0.79545(19) 0.08614(14) 0.14611(15) 0.0412(3) Uani d . 1.000 A .
C C1 0.9615(3) 0.34787(18) 0.16910(19) 0.0438(4) Uani d . 1.000 . .
C C2A 0.9571(3) 0.5227(2) 0.2371(3) 0.0611(6) Uani d PD 0.862(4) A 1
C C3A 0.7579(4) 0.5495(2) 0.2548(3) 0.0590(7) Uani d PD 0.862(4) A 1
C C4A 0.6807(3) 0.47256(19) 0.3468(2) 0.0531(5) Uani d PD 0.862(4) A 1
C C4C 0.6904(3) 0.30147(17) 0.27848(18) 0.0421(4) Uani d . 1.000 . .
C C4D 0.5783(2) 0.16637(17) 0.27860(17) 0.0396(4) Uani d . 1.000 A .
C C5 0.4231(3) 0.14228(19) 0.33927(19) 0.0443(4) Uani d . 1.000 . .
C C6 0.3399(2) -0.00860(19) 0.31681(18) 0.0430(4) Uani d . 1.000 A .
C C7 0.4130(2) -0.13824(18) 0.23121(19) 0.0444(4) Uani d . 1.000 . .
C C8 0.5640(2) -0.12039(18) 0.16959(19) 0.0426(4) Uani d . 1.000 A .
C C8A 0.6473(2) 0.03337(17) 0.19299(17) 0.0382(4) Uani d . 1.000 . .
C C9A 0.8222(2) 0.24863(17) 0.19625(18) 0.0406(4) Uani d . 1.000 A .
C C16 0.1720(3) -0.0386(2) 0.3790(2) 0.0530(5) Uani d . 1.000 . .
C C4B 0.6807(3) 0.47256(19) 0.3468(2) 0.0531(5) Uani d PD 0.138(4) A 2
C C3B 0.855(2) 0.5809(14) 0.3534(18) 0.0590(7) Uani d PD 0.138(4) A 2
C C2B 0.9571(3) 0.5227(2) 0.2371(3) 0.0611(6) Uani d PD 0.138(4) A 2
H H3A 0.65603 0.50556 0.14672 0.0708 Uiso calc PR 0.862(4) A 1
H H2B 0.98737 0.56293 0.16579 0.0733 Uiso calc PR 0.862(4) A 1
H H4B 0.54131 0.47484 0.33584 0.0637 Uiso calc PR 0.862(4) A 1
H H3B 0.77491 0.66471 0.31193 0.0708 Uiso calc PR 0.862(4) A 1
H H4A 0.76376 0.53281 0.46218 0.0637 Uiso calc PR 0.862(4) A 1
H H8 0.60931 -0.20752 0.11426 0.0512 Uiso calc R 1.000 . .
H H9 0.856(3) 0.029(3) 0.086(2) 0.050(5) Uiso d . 1.000 . .
H H16A 0.14149 0.06091 0.43500 0.0795 Uiso calc R 1.000 A .
H H16B 0.21516 -0.08010 0.45319 0.0795 Uiso calc R 1.000 . .
H H16C 0.05241 -0.11568 0.28852 0.0795 Uiso calc R 1.000 . .
H H5 0.37662 0.22852 0.39473 0.0531 Uiso calc R 1.000 A .
H H7 0.35612 -0.24001 0.21612 0.0532 Uiso calc R 1.000 A .
H H2A 1.06434 0.58601 0.34358 0.0733 Uiso calc PR 0.862(4) A 1
H H2C 1.09697 0.59042 0.28888 0.0733 Uiso calc PR 0.138(4) A 2
H H2D 0.89345 0.53906 0.14537 0.0733 Uiso calc PR 0.138(4) A 2
H H3C 0.80970 0.66932 0.34463 0.0708 Uiso calc PR 0.138(4) A 2
H H3D 0.95675 0.62673 0.46174 0.0708 Uiso calc PR 0.138(4) A 2
H H4C 0.55597 0.47686 0.27954 0.0637 Uiso calc PR 0.138(4) A 2
H H4D 0.67683 0.50937 0.45626 0.0637 Uiso calc PR 0.138(4) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 ' 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8A N9 C9A . . . 108.73(13) no
C8A N9 H9 . . . 127.5(19) no
C9A N9 H9 . . . 123.4(19) no
S1 C1 C2B . . . 121.48(16) no
C2A C1 C9A . . . 114.66(17) no
C2B C1 C9A . . . 114.66(17) no
S1 C1 C2A . . . 121.48(16) no
S1 C1 C9A . . . 123.85(14) no
C1 C2A C3A . . . 114.80(19) no
C1 C2B C3B . . . 118.3(6) no
C2A C3A C4A . . . 113.5(2) no
C2B C3B C4B . . . 121.0(10) no
C3A C4A C4C . . . 109.36(17) no
C3B C4B C4C . . . 112.2(6) no
C4B C4C C9A . . . 122.29(17) no
C4B C4C C4D . . . 130.69(18) no
C4A C4C C4D . . . 130.69(18) no
C4A C4C C9A . . . 122.29(17) no
C4D C4C C9A . . . 107.01(15) no
C4C C4D C5 . . . 134.04(17) no
C4C C4D C8A . . . 106.52(14) no
C5 C4D C8A . . . 119.43(16) no
C4D C5 C6 . . . 120.16(17) no
C7 C6 C16 . . . 119.78(17) no
C5 C6 C16 . . . 121.41(16) no
C5 C6 C7 . . . 118.81(16) no
C6 C7 C8 . . . 123.03(17) no
C7 C8 C8A . . . 117.67(15) no
N9 C8A C4D . . . 108.52(15) no
N9 C8A C8 . . . 130.59(15) no
C4D C8A C8 . . . 120.89(14) no
N9 C9A C4C . . . 109.22(15) no
C1 C9A C4C . . . 124.73(17) no
N9 C9A C1 . . . 126.04(15) no
C1 C2A H2A . . . 109.00 no
C1 C2A H2B . . . 109.00 no
C3A C2A H2A . . . 109.00 no
C3A C2A H2B . . . 109.00 no
H2A C2A H2B . . . 108.00 no
C1 C2B H2C . . . 108.00 no
C1 C2B H2D . . . 108.00 no
C3B C2B H2C . . . 108.00 no
C3B C2B H2D . . . 108.00 no
H2C C2B H2D . . . 107.00 no
C2A C3A H3B . . . 109.00 no
C4A C3A H3A . . . 109.00 no
C2A C3A H3A . . . 109.00 no
H3A C3A H3B . . . 108.00 no
C4A C3A H3B . . . 109.00 no
C2B C3B H3D . . . 107.00 no
C2B C3B H3C . . . 107.00 no
C4B C3B H3D . . . 107.00 no
H3C C3B H3D . . . 107.00 no
C4B C3B H3C . . . 107.00 no
C3A C4A H4A . . . 110.00 no
C3A C4A H4B . . . 110.00 no
H4A C4A H4B . . . 108.00 no
C4C C4A H4A . . . 110.00 no
C4C C4A H4B . . . 110.00 no
C4C C4B H4D . . . 109.00 no
H4C C4B H4D . . . 108.00 no
C3B C4B H4C . . . 109.00 no
C3B C4B H4D . . . 109.00 no
C4C C4B H4C . . . 109.00 no
C4D C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C6 C7 H7 . . . 119.00 no
C8 C7 H7 . . . 118.00 no
C7 C8 H8 . . . 121.00 no
C8A C8 H8 . . . 121.00 no
C6 C16 H16A . . . 109.00 no
C6 C16 H16B . . . 109.00 no
C6 C16 H16C . . . 109.00 no
H16A C16 H16B . . . 109.00 no
H16A C16 H16C . . . 109.00 no
H16B C16 H16C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . . 1.643(2) no
N9 C8A . . 1.359(2) no
N9 C9A . . 1.380(2) no
N9 H9 . . 0.86(2) no
C1 C9A . . 1.420(3) no
C1 C2B . . 1.519(3) no
C1 C2A . . 1.519(3) no
C2A C3A . . 1.508(4) no
C2B C3B . . 1.446(15) no
C3A C4A . . 1.520(3) no
C3B C4B . . 1.463(15) no
C4A C4C . . 1.498(3) no
C4B C4C . . 1.498(3) no
C4C C4D . . 1.415(3) no
C4C C9A . . 1.389(3) no
C4D C5 . . 1.406(3) no
C4D C8A . . 1.422(2) no
C5 C6 . . 1.376(3) no
C6 C16 . . 1.507(3) no
C6 C7 . . 1.419(2) no
C7 C8 . . 1.374(2) no
C8 C8A . . 1.398(3) no
C2A H2A . . 0.9700 no
C2A H2B . . 0.9700 no
C2B H2C . . 0.9700 no
C2B H2D . . 0.9700 no
C3A H3A . . 0.9700 no
C3A H3B . . 0.9700 no
C3B H3C . . 0.9700 no
C3B H3D . . 0.9700 no
C4A H4A . . 0.9700 no
C4A H4B . . 0.9700 no
C4B H4D . . 0.9700 no
C4B H4C . . 0.9700 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C16 H16C . . 0.9600 no
C16 H16A . . 0.9600 no
C16 H16B . . 0.9600 no
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
_geom_hbond_publ_flag
N9 H9 S1 2_755 0.86(2) 2.77(3) 3.4955(15) 143(2) yes
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
C9A N9 C8A C4D . . . . -1.01(16) no
C9A N9 C8A C8 . . . . 179.17(15) no
C8A N9 C9A C1 . . . . -179.28(15) no
C8A N9 C9A C4C . . . . 0.70(17) no
S1 C1 C2A C3A . . . . 155.86(17) no
C9A C1 C2A C3A . . . . -25.3(3) no
S1 C1 C9A N9 . . . . -1.7(2) no
S1 C1 C9A C4C . . . . 178.38(13) no
C2A C1 C9A N9 . . . . 179.56(16) no
C2A C1 C9A C4C . . . . -0.4(2) no
C1 C2A C3A C4A . . . . 51.1(3) no
C2A C3A C4A C4C . . . . -48.2(2) no
C3A C4A C4C C4D . . . . -155.34(19) no
C3A C4A C4C C9A . . . . 23.7(2) no
C4A C4C C4D C5 . . . . 0.2(3) no
C4A C4C C4D C8A . . . . 178.61(16) no
C9A C4C C4D C5 . . . . -178.95(17) no
C9A C4C C4D C8A . . . . -0.50(17) no
C4A C4C C9A N9 . . . . -179.30(14) no
C4A C4C C9A C1 . . . . 0.7(3) no
C4D C4C C9A N9 . . . . -0.11(17) no
C4D C4C C9A C1 . . . . 179.87(15) no
C4C C4D C5 C6 . . . . 178.74(17) no
C8A C4D C5 C6 . . . . 0.4(2) no
C4C C4D C8A N9 . . . . 0.93(17) no
C4C C4D C8A C8 . . . . -179.22(14) no
C5 C4D C8A N9 . . . . 179.65(14) no
C5 C4D C8A C8 . . . . -0.5(2) no
C4D C5 C6 C7 . . . . -0.3(2) no
C4D C5 C6 C16 . . . . -179.42(15) no
C5 C6 C7 C8 . . . . 0.2(2) no
C16 C6 C7 C8 . . . . 179.32(15) no
C6 C7 C8 C8A . . . . -0.2(2) no
C7 C8 C8A N9 . . . . -179.81(15) no
C7 C8 C8A C4D . . . . 0.4(2) no
