#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/32/2223293.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_2223293
loop_
_publ_author_name
'Ravichandran, K.'
'Sathiyaraj, K.'
'Ilango, S. S.'
'Ponnuswamy, S.'
'Ponnuswamy, M. N.'
_publ_section_title
2,2,4-Trimethyl-5-(4-tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine
_journal_coeditor_code           BT5042
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2363
_journal_page_last               o2364
_journal_paper_doi               10.1107/S1600536809034837
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H24 N2 O2 S'
_chemical_formula_moiety         'C19 H24 N2 O2 S'
_chemical_formula_sum            'C19 H24 N2 O2 S'
_chemical_formula_weight         344.46
_chemical_name_systematic
2,2,4-Trimethyl-5-(4-tolylsulfonyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3658(3)
_cell_length_b                   14.8013(8)
_cell_length_c                   17.4556(10)
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.40
_cell_measurement_theta_min      1.80
_cell_volume                     1903.07(17)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13544
_diffrn_reflns_theta_full        29.40
_diffrn_reflns_theta_max         29.40
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.186
_refine_ls_abs_structure_details 'Flack (1983), 2171 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1452
_reflns_number_gt                3278
_reflns_number_total             5154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5042.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

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

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223293
_cod_database_fobs_code          2223293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.08799(9) 0.63541(4) 0.80960(4) 0.0620(2) Uani d . 1 . .
O O1 0.2717(3) 0.63113(17) 0.78264(12) 0.0849(6) Uani d . 1 . .
O O2 0.0096(3) 0.55749(13) 0.84498(12) 0.0870(7) Uani d . 1 . .
N N1 -0.0887(3) 0.84795(14) 0.70370(13) 0.0566(5) Uani d . 1 . .
H H1 -0.072(4) 0.897(2) 0.6945(18) 0.073(9) Uiso d . 1 . .
C C2 -0.2833(3) 0.83013(16) 0.71790(15) 0.0520(6) Uani d . 1 . .
C C3 -0.3323(3) 0.73221(16) 0.70025(16) 0.0577(6) Uani d . 1 . .
H H3A -0.4623 0.7257 0.7074 0.069 Uiso calc R 1 . .
H H3B -0.3078 0.7218 0.6464 0.069 Uiso calc R 1 . .
C C4 -0.2402(3) 0.65759(15) 0.74511(17) 0.0589(7) Uani d . 1 . .
H H4 -0.2719 0.6642 0.7993 0.071 Uiso calc R 1 . .
N N5 -0.0387(3) 0.66325(13) 0.73728(11) 0.0524(5) Uani d . 1 . .
C C6 0.0396(3) 0.70241(16) 0.66986(13) 0.0497(6) Uani d . 1 . .
C C7 0.1455(3) 0.6493(2) 0.62250(16) 0.0659(7) Uani d . 1 . .
H H7 0.1565 0.5877 0.6320 0.079 Uiso calc R 1 . .
C C8 0.2354(4) 0.6879(3) 0.56082(18) 0.0855(10) Uani d . 1 . .
H H8 0.3070 0.6524 0.5289 0.103 Uiso calc R 1 . .
C C9 0.2182(4) 0.7779(3) 0.54737(17) 0.0862(11) Uani d . 1 . .
H H9 0.2819 0.8041 0.5071 0.103 Uiso calc R 1 . .
C C10 0.1077(4) 0.8310(2) 0.59246(15) 0.0676(7) Uani d . 1 . .
H H10 0.0954 0.8922 0.5814 0.081 Uiso calc R 1 . .
C C11 0.0141(3) 0.79417(17) 0.65442(13) 0.0501(6) Uani d . 1 . .
C C12 -0.3967(5) 0.8894(2) 0.6654(2) 0.0813(9) Uani d . 1 . .
H H12A -0.3735 0.9518 0.6767 0.122 Uiso calc R 1 . .
H H12B -0.5231 0.8766 0.6732 0.122 Uiso calc R 1 . .
H H12C -0.3652 0.8773 0.6130 0.122 Uiso calc R 1 . .
C C13 -0.3238(4) 0.8554(2) 0.80092(17) 0.0704(7) Uani d . 1 . .
H H13A -0.2526 0.8182 0.8345 0.106 Uiso calc R 1 . .
H H13B -0.4504 0.8460 0.8113 0.106 Uiso calc R 1 . .
H H13C -0.2939 0.9177 0.8092 0.106 Uiso calc R 1 . .
C C14 -0.3082(5) 0.5663(2) 0.7171(3) 0.0999(13) Uani d . 1 . .
H H14A -0.2821 0.5600 0.6635 0.150 Uiso calc R 1 . .
H H14B -0.4369 0.5623 0.7251 0.150 Uiso calc R 1 . .
H H14C -0.2485 0.5190 0.7451 0.150 Uiso calc R 1 . .
C C15 0.0750(3) 0.72366(16) 0.87704(14) 0.0516(5) Uani d . 1 . .
C C16 0.1482(4) 0.80712(19) 0.85876(15) 0.0640(7) Uani d . 1 . .
H H16 0.2035 0.8165 0.8115 0.077 Uiso calc R 1 . .
C C17 0.1378(4) 0.8753(2) 0.91126(17) 0.0759(8) Uani d . 1 . .
H H17 0.1873 0.9313 0.8988 0.091 Uiso calc R 1 . .
C C18 0.0569(4) 0.8647(2) 0.98198(17) 0.0722(7) Uani d . 1 . .
C C19 -0.0125(4) 0.7808(2) 0.99895(18) 0.0796(9) Uani d . 1 . .
H H19 -0.0666 0.7712 1.0464 0.095 Uiso calc R 1 . .
C C20 -0.0035(4) 0.7106(2) 0.94719(17) 0.0700(8) Uani d . 1 . .
H H20 -0.0508 0.6543 0.9600 0.084 Uiso calc R 1 . .
C C21 0.0455(7) 0.9425(3) 1.0377(2) 0.1170(14) Uani d . 1 . .
H H21A -0.0147 0.9229 1.0836 0.176 Uiso calc R 1 . .
H H21B -0.0217 0.9911 1.0150 0.176 Uiso calc R 1 . .
H H21C 0.1657 0.9628 1.0501 0.176 Uiso calc R 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'
O O 0.0106 0.0060 '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
O2 S1 O1 . . 119.16(14) ?
O2 S1 N5 . . 107.96(13) ?
O1 S1 N5 . . 107.36(11) ?
O2 S1 C15 . . 106.71(12) ?
O1 S1 C15 . . 107.67(14) ?
N5 S1 C15 . . 107.48(10) ?
C11 N1 C2 . . 121.86(19) ?
C11 N1 H1 . . 109(2) ?
C2 N1 H1 . . 112(3) ?
N1 C2 C12 . . 109.2(2) ?
N1 C2 C13 . . 107.8(2) ?
C12 C2 C13 . . 108.9(2) ?
N1 C2 C3 . . 111.42(19) ?
C12 C2 C3 . . 107.3(2) ?
C13 C2 C3 . . 112.2(2) ?
C4 C3 C2 . . 118.8(2) ?
C4 C3 H3A . . 107.6 ?
C2 C3 H3A . . 107.6 ?
C4 C3 H3B . . 107.6 ?
C2 C3 H3B . . 107.6 ?
H3A C3 H3B . . 107.0 ?
N5 C4 C3 . . 110.93(19) ?
N5 C4 C14 . . 110.3(2) ?
C3 C4 C14 . . 109.5(3) ?
N5 C4 H4 . . 108.7 ?
C3 C4 H4 . . 108.7 ?
C14 C4 H4 . . 108.7 ?
C6 N5 C4 . . 119.9(2) ?
C6 N5 S1 . . 120.68(16) ?
C4 N5 S1 . . 119.08(17) ?
C7 C6 C11 . . 120.9(2) ?
C7 C6 N5 . . 119.2(2) ?
C11 C6 N5 . . 119.8(2) ?
C6 C7 C8 . . 120.0(3) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 119.6(3) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C10 . . 121.0(3) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C10 C11 . . 120.8(3) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
N1 C11 C10 . . 121.6(2) ?
N1 C11 C6 . . 120.6(2) ?
C10 C11 C6 . . 117.6(2) ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 C14 H14A . . 109.5 ?
C4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C20 C15 C16 . . 119.8(3) ?
C20 C15 S1 . . 121.1(2) ?
C16 C15 S1 . . 119.09(19) ?
C17 C16 C15 . . 118.9(3) ?
C17 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
C16 C17 C18 . . 122.7(3) ?
C16 C17 H17 . . 118.7 ?
C18 C17 H17 . . 118.7 ?
C19 C18 C17 . . 117.2(3) ?
C19 C18 C21 . . 121.9(3) ?
C17 C18 C21 . . 120.9(3) ?
C18 C19 C20 . . 121.5(3) ?
C18 C19 H19 . . 119.3 ?
C20 C19 H19 . . 119.3 ?
C15 C20 C19 . . 120.0(3) ?
C15 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
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
S1 O2 . 1.430(2) ?
S1 O1 . 1.434(2) ?
S1 N5 . 1.623(2) ?
S1 C15 . 1.761(3) ?
N1 C11 . 1.395(3) ?
N1 C2 . 1.478(3) ?
N1 H1 . 0.75(3) ?
C2 C12 . 1.519(4) ?
C2 C13 . 1.526(4) ?
C2 C3 . 1.525(3) ?
C3 C4 . 1.515(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 N5 . 1.493(3) ?
C4 C14 . 1.522(4) ?
C4 H4 . 0.9800 ?
N5 C6 . 1.433(3) ?
C6 C7 . 1.382(3) ?
C6 C11 . 1.397(3) ?
C7 C8 . 1.387(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.359(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.378(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.394(3) ?
C10 H10 . 0.9300 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C20 . 1.368(4) ?
C15 C16 . 1.385(4) ?
C16 C17 . 1.366(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.380(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.375(4) ?
C18 C21 . 1.510(5) ?
C19 C20 . 1.379(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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
C20 H20 O2 1 0.93 2.51 2.885(4) 104.7
N1 H1 O2 3_556 0.75(3) 2.52(3) 3.268(3) 176(3)
C14 H14B O1 1_455 0.96 2.58 3.436(4) 148.6
C13 H13A Cg2 1_555 0.96 2.8987 3.759(3) 149.77
C19 H19 Cg2 3_556 0.93 2.8965 3.519(3) 125.53
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
C11 N1 C2 C12 . . . . -95.9(3) ?
C11 N1 C2 C13 . . . . 145.9(2) ?
C11 N1 C2 C3 . . . . 22.4(3) ?
N1 C2 C3 C4 . . . . 61.1(3) ?
C12 C2 C3 C4 . . . . -179.4(2) ?
C13 C2 C3 C4 . . . . -59.8(3) ?
C2 C3 C4 N5 . . . . -57.2(3) ?
C2 C3 C4 C14 . . . . -179.3(2) ?
C3 C4 N5 C6 . . . . -27.7(3) ?
C14 C4 N5 C6 . . . . 93.9(3) ?
C3 C4 N5 S1 . . . . 145.32(18) ?
C14 C4 N5 S1 . . . . -93.1(3) ?
O2 S1 N5 C6 . . . . -146.99(18) ?
O1 S1 N5 C6 . . . . -17.3(2) ?
C15 S1 N5 C6 . . . . 98.24(18) ?
O2 S1 N5 C4 . . . . 40.06(19) ?
O1 S1 N5 C4 . . . . 169.70(18) ?
C15 S1 N5 C4 . . . . -74.71(19) ?
C4 N5 C6 C7 . . . . -116.8(2) ?
S1 N5 C6 C7 . . . . 70.3(3) ?
C4 N5 C6 C11 . . . . 65.7(3) ?
S1 N5 C6 C11 . . . . -107.2(2) ?
C11 C6 C7 C8 . . . . 3.2(4) ?
N5 C6 C7 C8 . . . . -174.3(2) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
C7 C8 C9 C10 . . . . -2.3(5) ?
C8 C9 C10 C11 . . . . 1.7(4) ?
C2 N1 C11 C10 . . . . 123.8(3) ?
C2 N1 C11 C6 . . . . -62.0(3) ?
C9 C10 C11 N1 . . . . 175.7(2) ?
C9 C10 C11 C6 . . . . 1.3(4) ?
C7 C6 C11 N1 . . . . -178.1(2) ?
N5 C6 C11 N1 . . . . -0.7(3) ?
C7 C6 C11 C10 . . . . -3.7(3) ?
N5 C6 C11 C10 . . . . 173.7(2) ?
O2 S1 C15 C20 . . . . -1.4(3) ?
O1 S1 C15 C20 . . . . -130.5(2) ?
N5 S1 C15 C20 . . . . 114.2(2) ?
O2 S1 C15 C16 . . . . 177.6(2) ?
O1 S1 C15 C16 . . . . 48.5(2) ?
N5 S1 C15 C16 . . . . -66.8(2) ?
C20 C15 C16 C17 . . . . -1.0(4) ?
S1 C15 C16 C17 . . . . -180.0(2) ?
C15 C16 C17 C18 . . . . -0.1(4) ?
C16 C17 C18 C19 . . . . 1.0(4) ?
C16 C17 C18 C21 . . . . -178.9(3) ?
C17 C18 C19 C20 . . . . -0.8(5) ?
C21 C18 C19 C20 . . . . 179.1(3) ?
C16 C15 C20 C19 . . . . 1.2(4) ?
S1 C15 C20 C19 . . . . -179.8(2) ?
C18 C19 C20 C15 . . . . -0.3(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743221
