#------------------------------------------------------------------------------
#$Date: 2018-06-26 19:00:26 +0300 (Tue, 26 Jun 2018) $
#$Revision: 208654 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/96/1549605.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_1549605
loop_
_publ_author_name
'Seye, Dame'
'Diop, Cheikh Abdoul Khadir'
'Diop, Libasse'
'Geiger, David K.'
_publ_section_title
;
 Diisopropylammonium benzenesulfonate
;
_journal_coeditor_code           HB4233
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x180876
_journal_paper_doi               10.1107/S2414314618008763
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C6 H16 N +, C6 H5 O3 S -'
_chemical_formula_moiety         'C6 H16 N +, C6 H5 O3 S -'
_chemical_formula_sum            'C12 H21 N O3 S'
_chemical_formula_weight         259.36
_chemical_name_common
;
Diisopropylammonium benzenesulfonate
;
_chemical_name_systematic
;
Diisopropylammonium bis(propan-2-yl)azanium
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 106.616(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7370(13)
_cell_length_b                   8.8719(8)
_cell_length_c                   14.3722(16)
_cell_measurement_reflns_used    4767
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      25.0914
_cell_measurement_theta_min      2.7271
_cell_volume                     1434.1(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2  (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker X2S Benchtop'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11569
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.344
_refine_ls_extinction_coef       0.0085(18)
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.2880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                2104
_reflns_number_total             2910
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4233sup1.cif
_cod_data_source_block           I
_cod_database_code               1549605
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.71911(5) 0.49488(6) 0.84523(4) 0.0597(2) Uani d 1.0 . .
O O1 0.7417(3) 0.6492(3) 0.8574(3) 0.0749(12) Uani d 0.711(9) A 1
O O2 0.6149(3) 0.4620(6) 0.7613(3) 0.0911(15) Uani d 0.711(9) A 1
O O3 0.7116(4) 0.4164(4) 0.9309(3) 0.0989(19) Uani d 0.711(9) A 1
O O1A 0.6956(12) 0.6349(8) 0.7859(11) 0.102(4) Uani d 0.289(9) A 2
O O2A 0.6285(6) 0.3979(7) 0.8244(11) 0.087(4) Uani d 0.289(9) A 2
O O3A 0.7621(8) 0.5452(19) 0.9473(6) 0.131(7) Uani d 0.289(9) A 2
N N1 0.37129(18) 0.4253(2) 0.72964(14) 0.0541(5) Uani d 1.0 . .
H H1A 0.3478(19) 0.335(3) 0.7122(14) 0.059(6) Uiso d 1.0 . .
H H1B 0.452(2) 0.422(3) 0.7500(16) 0.071(7) Uiso d 1.0 . .
C C1 0.84060(18) 0.4120(2) 0.81419(16) 0.0532(5) Uani d 1.0 . .
C C2 0.8331(2) 0.3820(3) 0.71892(19) 0.0742(7) Uani d 1.0 . .
H H2 0.7635 0.4086 0.669 0.089 Uiso calc 1.0 . .
C C3 0.9270(3) 0.3130(4) 0.6959(3) 0.1026(10) Uani d 1.0 . .
H H3 0.9213 0.2918 0.6299 0.123 Uiso calc 1.0 . .
C C4 1.0259(3) 0.2755(4) 0.7654(3) 0.1098(12) Uani d 1.0 . .
H H4 1.0894 0.227 0.7485 0.132 Uiso calc 1.0 . .
C C5 1.0359(2) 0.3064(4) 0.8596(3) 0.1040(11) Uani d 1.0 . .
H H5 1.107 0.2812 0.9084 0.125 Uiso calc 1.0 . .
C C6 0.9420(2) 0.3753(3) 0.8858(2) 0.0769(7) Uani d 1.0 . .
H H6 0.9485 0.3963 0.952 0.092 Uiso calc 1.0 . .
C C7 0.3239(3) 0.5281(2) 0.64440(17) 0.0660(7) Uani d 1.0 . .
H H7 0.3422 0.6346 0.6664 0.079 Uiso calc 1.0 . .
C C8 0.3885(3) 0.4913(3) 0.5695(2) 0.1053(11) Uani d 1.0 . .
H H8A 0.4745 0.4962 0.5999 0.158 Uiso calc 1.0 . .
H H8B 0.3659 0.5643 0.5162 0.158 Uiso calc 1.0 . .
H H8C 0.3667 0.3896 0.544 0.158 Uiso calc 1.0 . .
C C9 0.1911(3) 0.5110(4) 0.6045(2) 0.0968(10) Uani d 1.0 . .
H H9A 0.1719 0.4063 0.5843 0.145 Uiso calc 1.0 . .
H H9B 0.1618 0.5778 0.5484 0.145 Uiso calc 1.0 . .
H H9C 0.1532 0.5378 0.6548 0.145 Uiso calc 1.0 . .
C C10 0.3368(2) 0.4608(3) 0.82055(16) 0.0628(6) Uani d 1.0 . .
H H10 0.2486 0.4748 0.8028 0.075 Uiso calc 1.0 . .
C C11 0.3956(3) 0.6040(3) 0.86640(18) 0.0797(8) Uani d 1.0 . .
H H11A 0.4819 0.5894 0.8886 0.119 Uiso calc 1.0 . .
H H11B 0.3666 0.6301 0.9219 0.119 Uiso calc 1.0 . .
H H11C 0.3766 0.6857 0.8186 0.119 Uiso calc 1.0 . .
C C12 0.3702(3) 0.3269(3) 0.8884(2) 0.0883(8) Uani d 1.0 . .
H H12A 0.4564 0.3115 0.906 0.132 Uiso calc 1.0 . .
H H12B 0.3297 0.2366 0.8559 0.132 Uiso calc 1.0 . .
H H12C 0.3461 0.3462 0.9473 0.132 Uiso calc 1.0 . .
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 O3 115.1(2)
O2A S1 O3A 116.2(6)
O1 S1 O2 112.2(2)
O3 S1 O2 111.3(2)
O2A S1 O1A 113.9(6)
O3A S1 O1A 105.8(6)
O2A S1 C1 108.8(3)
O1 S1 C1 107.50(14)
O3 S1 C1 105.38(14)
O3A S1 C1 107.7(4)
O2 S1 C1 104.49(14)
O1A S1 C1 103.5(3)
C7 N1 C10 116.82(17)
C7 N1 H1A 108.3(14)
C10 N1 H1A 107.7(14)
C7 N1 H1B 112.8(15)
C10 N1 H1B 104.0(15)
H1A N1 H1B 107.(2)
C6 C1 C2 119.8(2)
C6 C1 S1 119.83(19)
C2 C1 S1 120.32(18)
C1 C2 C3 119.8(3)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 120.8(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.3(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.5(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C1 C6 C5 118.8(3)
C1 C6 H6 120.6
C5 C6 H6 120.6
N1 C7 C9 110.5(2)
N1 C7 C8 107.7(2)
C9 C7 C8 112.3(2)
N1 C7 H7 108.7
C9 C7 H7 108.7
C8 C7 H7 108.7
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 N1 110.68(18)
C11 C10 C12 112.2(2)
N1 C10 C12 108.0(2)
C11 C10 H10 108.6
N1 C10 H10 108.6
C12 C10 H10 108.6
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2A 1.334(6)
S1 O1 1.396(3)
S1 O3 1.439(3)
S1 O3A 1.478(7)
S1 O2 1.481(3)
S1 O1A 1.487(7)
S1 C1 1.771(2)
N1 C7 1.501(3)
N1 C10 1.508(3)
N1 H1A 0.86(2)
N1 H1B 0.91(2)
C1 C6 1.372(3)
C1 C2 1.373(3)
C2 C3 1.381(4)
C2 H2 0.95
C3 C4 1.339(5)
C3 H3 0.95
C4 C5 1.354(5)
C4 H4 0.95
C5 C6 1.403(4)
C5 H5 0.95
C6 H6 0.95
C7 C9 1.507(4)
C7 C8 1.519(3)
C7 H7 1.0
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
C9 H9A 0.98
C9 H9B 0.98
C9 H9C 0.98
C10 C11 1.504(3)
C10 C12 1.516(3)
C10 H10 1.0
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
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
N1 H1A O1 2_646 0.86(2) 2.06(2) 2.893(4) 165.0(19) y
N1 H1A O1A 2_646 0.86(2) 1.85(2) 2.684(6) 163.(2) y
N1 H1B O2 . 0.91(2) 1.90(3) 2.782(4) 162.(2) y
N1 H1B O2A . 0.91(2) 2.05(3) 2.946(9) 167.(2) y
C8 H8A O2 . 0.98 2.45 3.246(5) 138 y
C9 H9A O1 2_646 0.98 2.54 3.313(4) 136 y
C11 H11B O3 3_667 0.98 2.57 3.493(4) 157 y
C7 H7 O2A 2_656 1.0 2.36 3.336(8) 166 n
C12 H12B O1A 2_646 0.98 2.17 2.944(11) 135 n
C12 H12C O3A 3_667 0.98 2.44 3.371(8) 159 n
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
O2A S1 C1 C6 -112.9(7)
O1 S1 C1 C6 82.8(3)
O3 S1 C1 C6 -40.4(3)
O3A S1 C1 C6 13.9(7)
O2 S1 C1 C6 -157.8(3)
O1A S1 C1 C6 125.6(7)
O2A S1 C1 C2 66.0(7)
O1 S1 C1 C2 -98.3(3)
O3 S1 C1 C2 138.5(3)
O3A S1 C1 C2 -167.2(7)
O2 S1 C1 C2 21.1(3)
O1A S1 C1 C2 -55.4(7)
C6 C1 C2 C3 1.0(4)
S1 C1 C2 C3 -178.0(2)
C1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 -0.7(5)
C3 C4 C5 C6 1.2(5)
C2 C1 C6 C5 -0.5(4)
S1 C1 C6 C5 178.4(2)
C4 C5 C6 C1 -0.6(4)
C10 N1 C7 C9 -68.0(3)
C10 N1 C7 C8 168.9(2)
C7 N1 C10 C11 -69.1(3)
C7 N1 C10 C12 167.7(2)

_cod_database_fobs_code 1549605
