#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/05/2240509.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_2240509
loop_
_publ_author_name
'Jeyaseelan, S.'
'Sowmya, B. R.'
'Venkateshappa, G.'
'Raghavendra Kumar, P.'
'Palakshamurthy, B. S.'
_publ_section_title
;
 Crystal structure of 1-benzylsulfonyl-1,2,3,4-tetrahydroquinoline
;
_journal_coeditor_code           HB7377
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o249
_journal_page_last               o250
_journal_paper_doi               10.1107/S2056989015004727
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H17 N O2 S'
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.36
_chemical_melting_point          514
_chemical_name_systematic
;
1-Benzylsulfonyl-1,2,3,4-tetrahydroquinoline
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.2430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5690(5)
_cell_length_b                   6.7128(2)
_cell_length_c                   16.8317(6)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1.7
_cell_volume                     1438.44(9)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 1.90
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and ω scans'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19601
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         1.672
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0563P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                2264
_reflns_number_total             2529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7377sup1.cif
_cod_data_source_block           I
_cod_database_code               2240509
_cod_database_fobs_code          2240509
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.961
#END Tags that were not found in dictionaries
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_occupancy
S S1 0.36706(3) 0.52581(6) 0.20696(2) 0.04077(16) Uani d 1
N N1 0.47088(9) 0.40403(18) 0.20485(8) 0.0377(3) Uani d 1
O O1 0.37882(9) 0.73063(17) 0.18920(8) 0.0515(3) Uani d 1
C C11 0.47391(11) 0.5739(2) 0.37732(10) 0.0395(4) Uani d 1
C C1 0.60202(12) 0.6674(2) 0.22242(10) 0.0419(4) Uani d 1
H H1 0.5827 0.7225 0.2656 0.050 Uiso calc 1
O O2 0.27373(9) 0.4236(2) 0.15618(8) 0.0634(4) Uani d 1
C C6 0.55139(11) 0.4980(2) 0.18039(9) 0.0334(3) Uani d 1
C C12 0.55291(13) 0.4389(3) 0.41491(11) 0.0488(4) Uani d 1
H H12 0.5430 0.3051 0.3999 0.059 Uiso calc 1
C C5 0.58183(13) 0.4084(2) 0.11812(10) 0.0448(4) Uani d 1
C C10 0.37241(13) 0.5045(3) 0.31416(11) 0.0477(4) Uani d 1
H H10A 0.3155 0.5818 0.3211 0.057 Uiso calc 1
H H10B 0.3615 0.3662 0.3257 0.057 Uiso calc 1
C C9 0.46039(15) 0.1865(2) 0.19022(11) 0.0516(4) Uani d 1
H H9A 0.4017 0.1368 0.2047 0.062 Uiso calc 1
H H9B 0.5236 0.1200 0.2260 0.062 Uiso calc 1
C C16 0.49091(15) 0.7733(3) 0.40037(12) 0.0547(4) Uani d 1
H H16 0.4387 0.8669 0.3758 0.066 Uiso calc 1
C C2 0.68073(13) 0.7538(3) 0.20020(13) 0.0555(5) Uani d 1
H H2 0.7137 0.8689 0.2275 0.067 Uiso calc 1
C C3 0.71051(15) 0.6695(3) 0.13749(14) 0.0679(6) Uani d 1
H H3 0.7633 0.7280 0.1221 0.081 Uiso calc 1
C C13 0.64626(15) 0.4993(3) 0.47439(12) 0.0632(5) Uani d 1
H H13 0.6984 0.4061 0.4996 0.076 Uiso calc 1
C C14 0.66280(15) 0.6951(4) 0.49666(12) 0.0646(6) Uani d 1
H H14 0.7262 0.7354 0.5366 0.078 Uiso calc 1
C C7 0.53441(17) 0.2149(3) 0.07532(12) 0.0625(5) Uani d 1
H H7A 0.5113 0.2333 0.0145 0.075 Uiso calc 1
H H7B 0.5885 0.1131 0.0903 0.075 Uiso calc 1
C C4 0.66236(16) 0.4995(3) 0.09785(14) 0.0634(5) Uani d 1
H H4 0.6840 0.4431 0.0562 0.076 Uiso calc 1
C C8 0.44285(18) 0.1420(3) 0.09850(13) 0.0667(6) Uani d 1
H H8A 0.4346 -0.0005 0.0888 0.080 Uiso calc 1
H H8B 0.3789 0.2067 0.0629 0.080 Uiso calc 1
C C15 0.58539(18) 0.8325(3) 0.45973(13) 0.0654(5) Uani d 1
H H15 0.5966 0.9662 0.4747 0.079 Uiso calc 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
O1 S1 O2 118.41(8)
O1 S1 N1 108.44(7)
O2 S1 N1 109.67(8)
O1 S1 C10 108.68(8)
O2 S1 C10 106.42(8)
N1 S1 C10 104.30(7)
C6 N1 C9 115.08(12)
C6 N1 S1 122.03(10)
C9 N1 S1 117.50(10)
C12 C11 C16 118.48(16)
C12 C11 C10 120.05(15)
C16 C11 C10 121.46(15)
C2 C1 C6 120.02(16)
C2 C1 H1 120.0
C6 C1 H1 120.0
C1 C6 C5 120.99(14)
C1 C6 N1 120.25(13)
C5 C6 N1 118.62(13)
C13 C12 C11 120.92(17)
C13 C12 H12 119.5
C11 C12 H12 119.5
C6 C5 C4 117.24(16)
C6 C5 C7 122.76(15)
C4 C5 C7 119.95(16)
C11 C10 S1 113.53(11)
C11 C10 H10A 108.9
S1 C10 H10A 108.9
C11 C10 H10B 108.9
S1 C10 H10B 108.9
H10A C10 H10B 107.7
N1 C9 C8 109.76(14)
N1 C9 H9A 109.7
C8 C9 H9A 109.7
N1 C9 H9B 109.7
C8 C9 H9B 109.7
H9A C9 H9B 108.2
C15 C16 C11 120.08(18)
C15 C16 H16 120.0
C11 C16 H16 120.0
C1 C2 C3 119.78(17)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 119.99(17)
C4 C3 H3 120.0
C2 C3 H3 120.0
C14 C13 C12 120.44(18)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.68(18)
C13 C14 H14 120.2
C15 C14 H14 120.2
C8 C7 C5 114.05(15)
C8 C7 H7A 108.7
C5 C7 H7A 108.7
C8 C7 H7B 108.7
C5 C7 H7B 108.7
H7A C7 H7B 107.6
C3 C4 C5 121.93(18)
C3 C4 H4 119.0
C5 C4 H4 119.0
C7 C8 C9 110.39(15)
C7 C8 H8A 109.6
C9 C8 H8A 109.6
C7 C8 H8B 109.6
C9 C8 H8B 109.6
H8A C8 H8B 108.1
C14 C15 C16 120.39(19)
C14 C15 H15 119.8
C16 C15 H15 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4277(12)
S1 O2 1.4341(12)
S1 N1 1.6397(13)
S1 C10 1.7863(18)
N1 C6 1.4397(18)
N1 C9 1.4794(19)
C11 C12 1.379(2)
C11 C16 1.390(2)
C11 C10 1.494(2)
C1 C2 1.376(2)
C1 C6 1.389(2)
C1 H1 0.9300
C6 C5 1.389(2)
C12 C13 1.376(3)
C12 H12 0.9300
C5 C4 1.394(3)
C5 C7 1.517(2)
C10 H10A 0.9700
C10 H10B 0.9700
C9 C8 1.508(3)
C9 H9A 0.9700
C9 H9B 0.9700
C16 C15 1.383(3)
C16 H16 0.9300
C2 C3 1.376(3)
C2 H2 0.9300
C3 C4 1.368(3)
C3 H3 0.9300
C13 C14 1.364(3)
C13 H13 0.9300
C14 C15 1.374(3)
C14 H14 0.9300
C7 C8 1.507(3)
C7 H7A 0.9700
C7 H7B 0.9700
C4 H4 0.9300
C8 H8A 0.9700
C8 H8B 0.9700
C15 H15 0.9300
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
C14 H14 O1 4_676 0.93 2.69 3.573(2) 158
C10 H10A O2 2 0.97 2.68 3.575(2) 153
