#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220730.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_2220730
loop_
_publ_author_name
'Umarani, P. R.'
'Marx, A.'
'Dhayalan, V.'
'Mohanakrishnan, A. K.'
'Manivannan, V.'
_publ_section_title
;
 1,3-Dimethylbenzo[b]dibenzothiophene
;
_journal_coeditor_code           BT2861
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o440
_journal_paper_doi               10.1107/S1600536809003456
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H14 S'
_chemical_formula_moiety         'C18 H14 S'
_chemical_formula_sum            'C18 H14 S'
_chemical_formula_weight         262.35
_chemical_name_systematic
;
1,3-Dimethylbenzo[b]dibenzothiophene
;
_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'
_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                 99.7870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0219(3)
_cell_length_b                   5.8692(5)
_cell_length_c                   22.8554(5)
_cell_measurement_reflns_used    6370
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.11
_cell_volume                     1324.80(12)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ'
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27929
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9605
_exptl_absorpt_correction_T_min  0.9436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0458
_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)+(0.0636P)²+0.5697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                2574
_reflns_number_total             3030
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2861.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220730
_cod_database_fobs_code          2220730
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
C C1 0.07838(18) -0.0783(3) 0.33166(8) 0.0456(4) Uani d . 1 . .
C C2 -0.0587(2) -0.0829(4) 0.30694(10) 0.0567(5) Uani d . 1 . .
H H2 -0.1153 -0.1953 0.3177 0.068 Uiso calc R 1 . .
C C3 -0.1081(2) 0.0813(4) 0.26653(9) 0.0603(6) Uani d . 1 . .
H H3 -0.1993 0.0801 0.2496 0.072 Uiso calc R 1 . .
C C4 -0.0245(2) 0.2490(4) 0.25047(9) 0.0579(5) Uani d . 1 . .
H H4 -0.0599 0.3589 0.2228 0.069 Uiso calc R 1 . .
C C5 0.1110(2) 0.2546(3) 0.27511(8) 0.0494(5) Uani d . 1 . .
H H5 0.1667 0.3678 0.2641 0.059 Uiso calc R 1 . .
C C6 0.16390(17) 0.0909(3) 0.31632(7) 0.0403(4) Uani d . 1 . .
C C7 0.30153(17) 0.0662(3) 0.34821(7) 0.0378(4) Uani d . 1 . .
C C8 0.41378(18) 0.1971(3) 0.34603(7) 0.0408(4) Uani d . 1 . .
H H8 0.4071 0.3228 0.3209 0.049 Uiso calc R 1 . .
C C9 0.53930(17) 0.1436(3) 0.38139(7) 0.0390(4) Uani d . 1 . .
C C10 0.65545(19) 0.2770(3) 0.37964(8) 0.0472(4) Uani d . 1 . .
H H10 0.6490 0.4027 0.3545 0.057 Uiso calc R 1 . .
C C11 0.77693(19) 0.2268(3) 0.41376(9) 0.0480(4) Uani d . 1 . .
C C12 0.78456(18) 0.0376(3) 0.45225(8) 0.0477(4) Uani d . 1 . .
H H12 0.8674 0.0037 0.4757 0.057 Uiso calc R 1 . .
C C13 0.67622(18) -0.0979(3) 0.45659(8) 0.0419(4) Uani d . 1 . .
C C14 0.54908(17) -0.0488(3) 0.41992(7) 0.0381(4) Uani d . 1 . .
C C15 0.43329(18) -0.1822(3) 0.42159(8) 0.0437(4) Uani d . 1 . .
H H15 0.4381 -0.3086 0.4464 0.052 Uiso calc R 1 . .
C C16 0.31376(18) -0.1253(3) 0.38656(8) 0.0418(4) Uani d . 1 . .
C C17 0.6892(2) -0.2914(4) 0.49988(9) 0.0523(5) Uani d . 1 . .
H H17A 0.7795 -0.2944 0.5222 0.078 Uiso calc R 1 . .
H H17B 0.6709 -0.4324 0.4787 0.078 Uiso calc R 1 . .
H H17C 0.6256 -0.2714 0.5265 0.078 Uiso calc R 1 . .
C C18 0.9007(2) 0.3703(4) 0.41279(11) 0.0648(6) Uani d . 1 . .
H H18A 0.9598 0.2941 0.3902 0.097 Uiso calc R 1 . .
H H18B 0.9471 0.3935 0.4527 0.097 Uiso calc R 1 . .
H H18C 0.8742 0.5149 0.3949 0.097 Uiso calc R 1 . .
S S1 0.16072(5) -0.26890(9) 0.38419(3) 0.0592(2) 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 0.0000 0.0000 '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
C2 C1 C6 . . 121.14(18) ?
C2 C1 S1 . . 125.84(16) ?
C6 C1 S1 . . 113.01(13) ?
C3 C2 C1 . . 118.62(19) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 120.96(19) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C4 C3 . . 120.53(19) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 119.81(19) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 118.93(16) ?
C5 C6 C7 . . 129.09(17) ?
C1 C6 C7 . . 111.98(15) ?
C8 C7 C16 . . 118.80(15) ?
C8 C7 C6 . . 129.86(16) ?
C16 C7 C6 . . 111.34(15) ?
C7 C8 C9 . . 120.82(16) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C10 C9 C8 . . 121.39(16) ?
C10 C9 C14 . . 119.18(16) ?
C8 C9 C14 . . 119.43(15) ?
C11 C10 C9 . . 121.72(18) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C10 C11 C12 . . 118.42(17) ?
C10 C11 C18 . . 122.00(19) ?
C12 C11 C18 . . 119.55(19) ?
C13 C12 C11 . . 123.04(17) ?
C13 C12 H12 . . 118.5 ?
C11 C12 H12 . . 118.5 ?
C12 C13 C14 . . 118.76(16) ?
C12 C13 C17 . . 120.64(17) ?
C14 C13 C17 . . 120.59(16) ?
C15 C14 C9 . . 119.19(16) ?
C15 C14 C13 . . 121.95(16) ?
C9 C14 C13 . . 118.85(15) ?
C16 C15 C14 . . 119.62(16) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C7 . . 122.13(16) ?
C15 C16 S1 . . 125.46(14) ?
C7 C16 S1 . . 112.39(13) ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C11 C18 H18A . . 109.5 ?
C11 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C11 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C1 S1 C16 . . 91.28(9) ?
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 C2 . 1.394(3) ?
C1 C6 . 1.395(3) ?
C1 S1 . 1.7425(19) ?
C2 C3 . 1.368(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.454(2) ?
C7 C8 . 1.370(2) ?
C7 C16 . 1.418(2) ?
C8 C9 . 1.410(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.409(2) ?
C9 C14 . 1.425(2) ?
C10 C11 . 1.362(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.411(3) ?
C11 C18 . 1.502(3) ?
C12 C13 . 1.363(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.430(2) ?
C13 C17 . 1.497(3) ?
C14 C15 . 1.406(2) ?
C15 C16 . 1.364(2) ?
C15 H15 . 0.9300 ?
C16 S1 . 1.7428(17) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C17 H17C Cg1 3_656 0.96 2.68 3.486(2) 142 y
C18 H18A Cg2 1_655 0.96 2.75 3.649(3) 155 y
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
C6 C1 C2 C3 . . . . 0.7(3) ?
S1 C1 C2 C3 . . . . 179.28(17) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
C2 C3 C4 C5 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 C1 . . . . 0.6(3) ?
C4 C5 C6 C7 . . . . -179.00(19) ?
C2 C1 C6 C5 . . . . -0.9(3) ?
S1 C1 C6 C5 . . . . -179.67(14) ?
C2 C1 C6 C7 . . . . 178.73(18) ?
S1 C1 C6 C7 . . . . 0.0(2) ?
C5 C6 C7 C8 . . . . 0.2(3) ?
C1 C6 C7 C8 . . . . -179.43(18) ?
C5 C6 C7 C16 . . . . -179.98(18) ?
C1 C6 C7 C16 . . . . 0.4(2) ?
C16 C7 C8 C9 . . . . -0.3(3) ?
C6 C7 C8 C9 . . . . 179.59(17) ?
C7 C8 C9 C10 . . . . -179.90(16) ?
C7 C8 C9 C14 . . . . -0.1(3) ?
C8 C9 C10 C11 . . . . 179.83(18) ?
C14 C9 C10 C11 . . . . 0.1(3) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
C9 C10 C11 C18 . . . . -179.07(19) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C18 C11 C12 C13 . . . . 178.60(19) ?
C11 C12 C13 C14 . . . . 0.9(3) ?
C11 C12 C13 C17 . . . . -177.74(17) ?
C10 C9 C14 C15 . . . . -179.87(16) ?
C8 C9 C14 C15 . . . . 0.4(3) ?
C10 C9 C14 C13 . . . . 1.3(2) ?
C8 C9 C14 C13 . . . . -178.50(16) ?
C12 C13 C14 C15 . . . . 179.42(17) ?
C17 C13 C14 C15 . . . . -1.9(3) ?
C12 C13 C14 C9 . . . . -1.7(3) ?
C17 C13 C14 C9 . . . . 176.94(16) ?
C9 C14 C15 C16 . . . . -0.2(3) ?
C13 C14 C15 C16 . . . . 178.66(17) ?
C14 C15 C16 C7 . . . . -0.3(3) ?
C14 C15 C16 S1 . . . . -178.84(14) ?
C8 C7 C16 C15 . . . . 0.5(3) ?
C6 C7 C16 C15 . . . . -179.40(17) ?
C8 C7 C16 S1 . . . . 179.24(13) ?
C6 C7 C16 S1 . . . . -0.65(19) ?
C2 C1 S1 C16 . . . . -179.0(2) ?
C6 C1 S1 C16 . . . . -0.29(15) ?
C15 C16 S1 C1 . . . . 179.24(18) ?
C7 C16 S1 C1 . . . . 0.54(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741674
