#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/39/2003952.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_2003952
loop_
_publ_author_name
'Ng, S. W.'
_publ_section_title
;
 Dicyclohexylammonium 2-Carboxybenzenesulfonate Dihydrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1853
_journal_page_last               1855
_journal_paper_doi               10.1107/S0108270195003118
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C12 H24 N , C7 H5 O5 S , 2H2 O'
_chemical_formula_sum            'C19 H33 N O7 S'
_chemical_formula_weight         419.52
_chemical_name_systematic
;
 dicyclohexylammonium hydrogen 2-sulfobenzoate dihydrate
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 94.48(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.140(6)
_cell_length_b                   9.586(3)
_cell_length_c                   16.118(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11
_cell_measurement_theta_min      8
_cell_volume                     2178.1(15)
_computing_cell_refinement
;
CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988)
;
_computing_data_collection
;
CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988)
;
_computing_data_reduction
;
CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution
;
MULTAN80 (Main, Fiske, Hull, Lessinger, Germain, Declercq & Woolfson, 1980)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω-2θ
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2966
_diffrn_reflns_theta_max         22.47
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        1.9
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.009
_refine_ls_goodness_of_fit_obs   1.075
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_obs          0.0575
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0649P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1509
_refine_ls_wR_factor_obs         0.1188
_reflns_number_observed          1648
_reflns_number_total             2831
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ta1017.cif
_cod_data_source_block           ta1017
_cod_original_cell_volume        2178.0(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2003952
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_label
_atom_site_occupancy
_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_type_symbol
S 1 0.59719(9) 0.48665(14) 0.21607(8) 0.0395(4) Uani d . S
OW1 1 0.3811(3) 0.6129(6) 0.5031(2) 0.0746(13) Uani d . O
OW2 1 0.2728(3) 0.7465(5) 0.6116(2) 0.0796(14) Uani d . O
O1 1 0.6563(2) 0.3649(4) 0.2324(2) 0.0521(10) Uani d . O
O2 1 0.6271(3) 0.5661(5) 0.1469(2) 0.0745(13) Uani d . O
O3 1 0.5862(2) 0.5654(4) 0.2905(2) 0.0619(12) Uani d . O
O4 1 0.4629(3) 0.3647(4) 0.3785(2) 0.0662(12) Uani d . O
O5 1 0.3737(3) 0.5485(4) 0.3460(2) 0.0559(11) Uani d . O
N 1 0.6900(3) 0.7877(4) 0.3629(2) 0.0349(10) Uani d . N
C1 1 0.4210(4) 0.4368(6) 0.3273(3) 0.0392(13) Uani d . C
C2 1 0.4117(3) 0.4040(5) 0.2359(3) 0.0340(12) Uani d . C
C3 1 0.4828(3) 0.4221(5) 0.1822(3) 0.0315(12) Uani d . C
C4 1 0.4676(4) 0.3843(5) 0.0994(3) 0.0430(13) Uani d . C
H4 1 0.5152(4) 0.3979(5) 0.0636(3) 0.065 Uiso calc R H
C5 1 0.3827(4) 0.3268(6) 0.0699(3) 0.053(2) Uani d . C
H5 1 0.3731(4) 0.3012(6) 0.0142(3) 0.079 Uiso calc R H
C6 1 0.3115(4) 0.3068(6) 0.1226(4) 0.056(2) Uani d . C
H6 1 0.2542(4) 0.2667(6) 0.1028(4) 0.084 Uiso calc R H
C7 1 0.3257(4) 0.3470(6) 0.2051(3) 0.0489(14) Uani d . C
H7 1 0.2772(4) 0.3356(6) 0.2403(3) 0.073 Uiso calc R H
C8 1 0.6151(4) 0.8996(5) 0.3598(3) 0.0406(13) Uani d . C
H8 1 0.6406(4) 0.9810(5) 0.3908(3) 0.061 Uiso calc R H
C9 1 0.5286(3) 0.8499(5) 0.3986(3) 0.0461(14) Uani d . C
H9A 1 0.5443(3) 0.8304(5) 0.4571(3) 0.069 Uiso calc R H
H9B 1 0.5060(3) 0.7642(5) 0.3718(3) 0.069 Uiso calc R H
C10 1 0.4509(4) 0.9602(6) 0.3895(4) 0.065(2) Uani d . C
H10A 1 0.3946(4) 0.9255(6) 0.4133(4) 0.098 Uiso calc R H
H10B 1 0.4719(4) 1.0433(6) 0.4200(4) 0.098 Uiso calc R H
C11 1 0.4270(4) 0.9973(7) 0.2989(4) 0.067(2) Uani d . C
H11A 1 0.3785(4) 1.0690(7) 0.2949(4) 0.101 Uiso calc R H
H11B 1 0.4021(4) 0.9157(7) 0.2691(4) 0.101 Uiso calc R H
C12 1 0.5144(4) 1.0493(6) 0.2597(4) 0.058(2) Uani d . C
H12A 1 0.5359(4) 1.1358(6) 0.2862(4) 0.087 Uiso calc R H
H12B 1 0.4988(4) 1.0678(6) 0.2011(4) 0.087 Uiso calc R H
C13 1 0.5935(4) 0.9410(6) 0.2696(3) 0.0509(15) Uani d . C
H13A 1 0.5748(4) 0.8588(6) 0.2372(3) 0.076 Uiso calc R H
H13B 1 0.6503(4) 0.9786(6) 0.2480(3) 0.076 Uiso calc R H
C14 1 0.7272(3) 0.7305(5) 0.4464(3) 0.0403(13) Uani d . C
H14 1 0.6757(3) 0.6815(5) 0.4714(3) 0.060 Uiso calc R H
C15 1 0.7638(4) 0.8455(6) 0.5047(3) 0.0468(14) Uani d . C
H15A 1 0.7121(4) 0.9070(6) 0.5164(3) 0.070 Uiso calc R H
H15B 1 0.8111(4) 0.9000(6) 0.4786(3) 0.070 Uiso calc R H
C16 1 0.8079(5) 0.7827(7) 0.5860(3) 0.074(2) Uani d . C
H16A 1 0.8330(5) 0.8569(7) 0.6222(3) 0.111 Uiso calc R H
H16B 1 0.7593(5) 0.7344(7) 0.6141(3) 0.111 Uiso calc R H
C17 1 0.8869(5) 0.6814(7) 0.5701(4) 0.078(2) Uani d . C
H17A 1 0.9122(5) 0.6411(7) 0.6223(4) 0.117 Uiso calc R H
H17B 1 0.9378(5) 0.7309(7) 0.5457(4) 0.117 Uiso calc R H
C18 1 0.8498(5) 0.5658(7) 0.5114(4) 0.073(2) Uani d . C
H18A 1 0.8034(5) 0.5106(7) 0.5382(4) 0.110 Uiso calc R H
H18B 1 0.9018(5) 0.5049(7) 0.4993(4) 0.110 Uiso calc R H
C19 1 0.8042(4) 0.6264(6) 0.4303(3) 0.057(2) Uani d . C
H19A 1 0.8525(4) 0.6721(6) 0.4004(3) 0.085 Uiso calc R H
H19B 1 0.7773(4) 0.5514(6) 0.3957(3) 0.085 Uiso calc R H
H27 1 0.7395(4) 0.8208(6) 0.3376(3) 0.091(23) Uiso d R H
H28 1 0.6663(4) 0.7150(6) 0.3320(3) 0.054(16) Uiso d R H
H29 1 0.3718(4) 0.5734(6) 0.4029(3) 0.149(33) Uiso d R H
H30 1 0.4418(4) 0.6044(6) 0.5439(3) 0.096(21) Uiso d R H
H31 1 0.3948(4) 0.6994(6) 0.5019(3) 0.085(28) Uiso d R H
H32 1 0.2328(4) 0.8044(6) 0.6419(3) 0.131(29) Uiso d R H
H33 1 0.3218(4) 0.7224(6) 0.6649(3) 0.252(54) Uiso d R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.0060
S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1246 0.1234
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 S O3 111.7(2) yes
O1 S O2 111.5(2) yes
O1 S C3 105.9(2) yes
O2 S O3 115.2(3) yes
O2 S C3 105.1(2) yes
O3 S C3 106.5(2) yes
C8 N C14 119.0(4) yes
O4 C1 O5 123.1(5) yes
O4 C1 C2 123.8(5) yes
O5 C1 C2 113.0(5) yes
C1 C2 C3 125.0(4) yes
C1 C2 C7 116.1(4) yes
C3 C2 C7 118.9(4) yes
S C3 C2 122.5(3) yes
S C3 C4 117.2(4) yes
C2 C3 C4 120.2(4) yes
C3 C4 C5 120.4(5) yes
C4 C5 C6 120.2(5) yes
C5 C6 C7 119.6(5) yes
C2 C7 C6 120.7(5) yes
N C8 C9 110.8(4) yes
N C8 C13 107.9(4) yes
C9 C8 C13 112.0(4) yes
N C8 C13 107.9(4) yes
C8 C9 C10 110.2(4) yes
C9 C10 C11 111.1(5) yes
C10 C11 C12 110.6(5) yes
C11 C12 C13 110.3(5) yes
C8 C13 C12 111.7(5) yes
N C14 C15 111.6(4) yes
N C14 C19 107.0(4) yes
C15 C14 C19 111.7(4) yes
C14 C15 C16 110.0(5) yes
C15 C16 C17 111.3(5) yes
C16 C17 C18 110.4(5) yes
C17 C18 C19 110.9(5) yes
C14 C19 C18 111.5(5) yes
O5 OW1 OW2 138.8(2) no
O5 OW1 O4 40.79(12) no
OW2 OW1 O4 161.2(2) no
O5 OW2 O1 19.96(5) no
S O3 N 131.5(2) no
C1 O4 OW1 80.2(3) no
C1 O5 OW1 115.9(3) no
C1 O5 OW2 133.9(3) no
C8 N O3 100.6(3) no
C14 N O3 103.3(3) no
C8 N O1 124.6(3) no
C14 N O1 96.0(3) no
O3 N O1 25.67(9) no
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
S O1 . 1.447(4) yes
S O2 . 1.441(4) yes
S O3 . 1.436(3) yes
S C3 . 1.778(5) yes
O4 C1 . 1.198(6) yes
O5 C1 . 1.310(6) yes
N C8 . 1.506(6) yes
N C14 . 1.509(6) yes
C1 C2 . 1.502(7) yes
C2 C3 . 1.388(6) yes
C2 C7 . 1.389(7) yes
C3 C4 . 1.382(6) yes
C4 C5 . 1.372(7) yes
C5 C6 . 1.380(7) yes
C6 C7 . 1.384(7) yes
C8 C9 . 1.495(6) yes
C8 C13 . 1.515(7) yes
C9 C10 . 1.523(7) yes
C10 C11 . 1.515(8) yes
C11 C12 . 1.515(8) yes
C12 C13 . 1.525(7) yes
C14 C15 . 1.514(6) yes
C14 C19 . 1.514(7) yes
C15 C16 . 1.529(7) yes
C16 C17 . 1.517(8) yes
C17 C18 . 1.523(8) yes
C18 C19 . 1.526(7) yes
OW1 OW2 . 2.732(6) yes
OW1 O4 3_666 2.810(6) yes
OW1 O5 . 2.600(5) yes
OW2 O1 3_666 2.841(6) yes
OW2 O2 4_576 2.825(6) yes
O1 N 2_645 2.855(5) yes
O3 N . 2.791(5) yes
