#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/62/2006231.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_2006231
loop_
_publ_author_name
'Ng, Seik Weng'
_publ_section_title
;
 Dicyclohexylammonium
 (N,N-Dicyclohexylthiocarbamoylthio)acetate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              779
_journal_page_last               781
_journal_paper_doi               10.1107/S0108270197000644
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C12 H24 N1 1+, C15 H24 N1 O2 S2 1-'
_chemical_formula_moiety         'C~12~H~24~N 1+, C~15~H~24~NO~2~S~2~ 1-'
_chemical_formula_sum            'C27 H48 N2 O2 S2'
_chemical_formula_weight         496.79
_chemical_name_systematic
;
 Dicyclohexylammonium (N,N-Dicyclohexylthiocarbamoylthio)acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 95.203(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2523(7)
_cell_length_b                   30.1160(10)
_cell_length_c                   10.2195(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      14
_cell_volume                     2835.9(3)
_computing_cell_refinement       'CAD-4 VAX/PC'
_computing_data_collection       'CAD-4 VAX/PC (Enraf-Nonius, 1988)'
_computing_data_reduction
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5288
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.35
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   '\y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.135
_refine_ls_hydrogen_treatment
;
H atoms: riding with U(H) = 1.5U~eq~(C); ammonium H atoms were
located and refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.075
_refine_ls_restrained_S_obs      1.178
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_obs          .0453
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0719P)²+0.2946P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1249
_refine_ls_wR_factor_obs         .1150
_reflns_number_observed          3645
_reflns_number_total             4966
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            kh1126.cif
_cod_data_source_block           ipt133
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.2946P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.2946P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2006231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
loop_
_atom_site_label
_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_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 .27492(6) .13738(2) .68776(7) .0630(2) Uani d . 1 . S
S2 .53582(8) .16493(2) .86079(6) .0661(2) Uani d . 1 . S
O1 .2778(2) .05463(5) .9858(2) .0670(5) Uani d . 1 . O
O2 .4016(2) .05290(5) .8090(2) .0560(4) Uani d . 1 . O
N1 .4944(2) .18132(6) .6035(2) .0499(4) Uani d D 1 . N
N2 .3223(2) -.02538(6) 1.1032(2) .0385(4) Uani d . 1 . N
H1 .318(3) .0021(9) 1.055(2) .066(7) Uiso d . 1 . H
H2 .422(3) -.0319(8) 1.132(2) .062(7) Uiso d . 1 . H
C1 .3158(2) .07010(7) .8805(2) .0464(5) Uani d . 1 . C
C2 .2458(3) .11444(8) .8448(3) .0672(7) Uani d . 1 . C
H2A .2804(3) .13578(8) .9115(3) .101 Uiso calc R 1 . H
H2B .1420(3) .11137(8) .8491(3) .101 Uiso calc R 1 . H
C3 .4467(2) .16351(7) .7116(2) .0443(5) Uani d . 1 . C
C4 .4336(6) .1863(3) .4670(6) .040(2) Uani d PD .50 1 C
H4 .5052(6) .2021(3) .4193(6) .060 Uiso calc PR .50 1 H
C5 .3960(10) .1430(3) .3940(10) .041(2) Uani d PD .50 1 C
H5A .3160(10) .1282(3) .4310(10) .062 Uiso calc PR .50 1 H
H5B .4790(10) .1232(3) .3990(10) .062 Uiso calc PR .50 1 H
C6 .3520(10) .1561(3) .2498(9) .055(2) Uani d PD .50 1 C
H6A .4310(10) .1719(3) .2141(9) .083 Uiso calc PR .50 1 H
H6B .3310(10) .1297(3) .1972(9) .083 Uiso calc PR .50 1 H
C7 .2176(9) .1857(3) .2458(8) .062(2) Uani d PD .50 1 C
H7A .1398(9) .1703(3) .2843(8) .093 Uiso calc PR .50 1 H
H7B .1848(9) .1929(3) .1554(8) .093 Uiso calc PR .50 1 H
C8 .2570(10) .2285(4) .3232(9) .050(2) Uani d PD .50 1 C
H8A .1740(10) .2485(4) .3172(9) .075 Uiso calc PR .50 1 H
H8B .3370(10) .2434(4) .2867(9) .075 Uiso calc PR .50 1 H
C9 .2993(6) .2162(2) .4684(5) .0420(10) Uani d PD .50 1 C
H9A .3218(6) .2426(2) .5204(5) .063 Uiso calc PR .50 1 H
H9B .2208(6) .2004(2) .5050(5) .063 Uiso calc PR .50 1 H
C4' .3820(7) .1833(3) .4831(6) .045(2) Uani d PD .50 2 C
H4' .2929(7) .1716(3) .5151(6) .068 Uiso calc PR .50 2 H
C5' .4200(10) .1498(4) .3800(10) .059(4) Uani d PD .50 2 C
H5'1 .4340(10) .1209(4) .4220(10) .089 Uiso calc PR .50 2 H
H5'2 .5110(10) .1584(4) .3480(10) .089 Uiso calc PR .50 2 H
C6' .3050(10) .1457(3) .2640(10) .080(3) Uani d PD .50 2 C
H6'1 .3430(10) .1272(3) .1970(10) .120 Uiso calc PR .50 2 H
H6'2 .2200(10) .1310(3) .2930(10) .120 Uiso calc PR .50 2 H
C7' .2610(10) .1901(3) .2049(8) .069(2) Uani d PD .50 2 C
H7'1 .1780(10) .1860(3) .1409(8) .104 Uiso calc PR .50 2 H
H7'2 .3400(10) .2018(3) .1590(8) .104 Uiso calc PR .50 2 H
C8' .2220(10) .2236(4) .3070(10) .066(4) Uani d PD .50 2 C
H8'1 .1310(10) .2149(4) .3400(10) .100 Uiso calc PR .50 2 H
H8'2 .2080(10) .2524(4) .2650(10) .100 Uiso calc PR .50 2 H
C9' .3370(10) .2277(2) .4228(8) .082(2) Uani d PD .50 2 C
H9'1 .4220(10) .2423(2) .3934(8) .122 Uiso calc PR .50 2 H
H9'2 .3000(10) .2464(2) .4895(8) .122 Uiso calc PR .50 2 H
C10 .6554(6) .1945(2) .6253(7) .042(2) Uani d PD .50 3 C
H10 .6995(6) .1831(2) .7095(7) .064 Uiso calc PR .50 3 H
C11 .7446(9) .1799(3) .5105(7) .061(2) Uani d PD .50 3 C
H11A .7095(9) .1947(3) .4294(7) .091 Uiso calc PR .50 3 H
H11B .7384(9) .1481(3) .4972(7) .091 Uiso calc PR .50 3 H
C12 .9040(10) .1942(4) .555(2) .089(5) Uani d PD .50 3 C
H12A .9310(10) .1853(4) .645(2) .134 Uiso calc PR .50 3 H
H12B .9720(10) .1809(4) .499(2) .134 Uiso calc PR .50 3 H
C13 .9047(9) .2450(4) .5420(7) .071(3) Uani d PD .50 3 C
H13A .8589(9) .2543(4) .4573(7) .107 Uiso calc PR .50 3 H
H13B 1.0029(9) .2566(4) .5527(7) .107 Uiso calc PR .50 3 H
C14 .8170(10) .2607(4) .6540(10) .070(3) Uani d PD .50 3 C
H14A .8210(10) .2928(4) .6620(10) .105 Uiso calc PR .50 3 H
H14B .8560(10) .2481(4) .7370(10) .105 Uiso calc PR .50 3 H
C15 .6570(10) .2455(3) .623(2) .060(4) Uani d PD .50 3 C
H15A .5970(10) .2572(3) .688(2) .089 Uiso calc PR .50 3 H
H15B .6200(10) .2563(3) .537(2) .089 Uiso calc PR .50 3 H
C10' .6293(7) .2037(2) .5866(9) .059(2) Uani d PD .50 4 C
H10' .6101(7) .2124(2) .4943(9) .089 Uiso calc PR .50 4 H
C11' .7447(8) .1702(3) .5723(9) .075(3) Uani d PD .50 4 C
H11C .7098(8) .1485(3) .5067(9) .113 Uiso calc PR .50 4 H
H11D .7654(8) .1547(3) .6551(9) .113 Uiso calc PR .50 4 H
C12' .8850(10) .1910(4) .532(2) .080(4) Uani d PD .50 4 C
H12C .9630(10) .1700(4) .550(2) .120 Uiso calc PR .50 4 H
H12D .8740(10) .1961(4) .438(2) .120 Uiso calc PR .50 4 H
C13' .9260(10) .2338(4) .5990(10) .106(4) Uani d PD .50 4 C
H13C 1.0010(10) .2476(4) .5530(10) .159 Uiso calc PR .50 4 H
H13D .9690(10) .2269(4) .6870(10) .159 Uiso calc PR .50 4 H
C14' .807(2) .2674(4) .6110(10) .088(5) Uani d PD .50 4 C
H14C .791(2) .2832(4) .5280(10) .133 Uiso calc PR .50 4 H
H14D .841(2) .2888(4) .6780(10) .133 Uiso calc PR .50 4 H
C15' .6630(10) .2484(3) .645(2) .064(4) Uani d PD .50 4 C
H15C .6650(10) .2462(3) .740(2) .096 Uiso calc PR .50 4 H
H15D .5860(10) .2688(3) .615(2) .096 Uiso calc PR .50 4 H
C16 .2513(2) -.01666(6) 1.2271(2) .0407(5) Uani d . 1 . C
H16 .1547(2) -.00429(6) 1.2027(2) .061 Uiso calc R 1 . H
C17 .3392(3) .01768(8) 1.3071(2) .0585(6) Uani d . 1 . C
H17A .3450(3) .04459(8) 1.2557(2) .088 Uiso calc R 1 . H
H17B .4370(3) .00668(8) 1.3282(2) .088 Uiso calc R 1 . H
C18 .2706(3) .02832(9) 1.4344(2) .0720(7) Uani d . 1 . C
H18A .3332(3) .04859(9) 1.4870(2) .108 Uiso calc R 1 . H
H18B .1781(3) .04297(9) 1.4131(2) .108 Uiso calc R 1 . H
C19 .2476(3) -.01305(9) 1.5130(2) .0739(8) Uani d . 1 . C
H19A .1960(3) -.00548(9) 1.5884(2) .111 Uiso calc R 1 . H
H19B .3409(3) -.02542(9) 1.5450(2) .111 Uiso calc R 1 . H
C20 .1617(3) -.04737(9) 1.4305(2) .0680(7) Uani d . 1 . C
H20A .0646(3) -.03617(9) 1.4065(2) .102 Uiso calc R 1 . H
H20B .1533(3) -.07417(9) 1.4819(2) .102 Uiso calc R 1 . H
C21 .2335(3) -.05847(7) 1.3066(2) .0532(6) Uani d . 1 . C
H21A .3278(3) -.07179(7) 1.3300(2) .080 Uiso calc R 1 . H
H21B .1744(3) -.07973(7) 1.2543(2) .080 Uiso calc R 1 . H
C22 .2592(2) -.06181(6) 1.0154(2) .0386(4) Uani d . 1 . C
H22 .2740(2) -.09012(6) 1.0620(2) .058 Uiso calc R 1 . H
C23 .3407(2) -.06333(8) .8933(2) .0496(5) Uani d . 1 . C
H23A .4432(2) -.06818(8) .9183(2) .074 Uiso calc R 1 . H
H23B .3303(2) -.03513(8) .8475(2) .074 Uiso calc R 1 . H
C24 .2819(3) -.10060(9) .8023(2) .0609(6) Uani d . 1 . C
H24A .3301(3) -.09972(9) .7220(2) .091 Uiso calc R 1 . H
H24B .3035(3) -.12899(9) .8445(2) .091 Uiso calc R 1 . H
C25 .1196(3) -.09669(9) .7688(2) .0664(7) Uani d . 1 . C
H25A .0851(3) -.12239(9) .7180(2) .100 Uiso calc R 1 . H
H25B .0991(3) -.07049(9) .7151(2) .100 Uiso calc R 1 . H
C26 .0394(2) -.09350(9) .8915(2) .0626(7) Uani d . 1 . C
H26A .0498(2) -.12122(9) .9397(2) .094 Uiso calc R 1 . H
H26B -.0631(2) -.08881(9) .8665(2) .094 Uiso calc R 1 . H
C27 .0976(2) -.05567(8) .9792(2) .0486(5) Uani d . 1 . C
H27A .0472(2) -.05498(8) 1.0584(2) .073 Uiso calc R 1 . H
H27B .0805(2) -.02763(8) .9337(2) .073 Uiso calc R 1 . H
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
_geom_angle_publ_flag
C2 S1 C3 104.70(10) yes
C3 N1 C4 134.5(3) yes
C3 N1 C10 111.8(3) yes
C3 N1 C4' 115.2(3) yes
C3 N1 C10' 129.8(4) yes
C16 N2 C22 117.1(2) yes
C4 N1 C10 113.2(4) yes
C4' N1 C10' 114.4(4) yes
O1 C1 O2 126.5(2) yes
O2 C1 C2 120.6(2) yes
O1 C1 C2 112.9(2) yes
C1 C2 S1 117.5(2) yes
N1 C3 S2 124.8(2) yes
N1 C3 S1 115.1(2) yes
S2 C3 S1 120.10(10) yes
N1 C4 C5 115.5(6) yes
N1 C4 C9 107.0(4) yes
C5 C4 C9 110.7(6) no
C4 C5 C6 106.2(7) no
C5 C6 C7 108.5(7) no
C6 C7 C8 108.9(7) no
C7 C8 C9 108.6(7) no
C8 C9 C4 105.6(6) no
C9' C4' N1 120.0(6) yes
C5' C4' N1 110.1(6) yes
C9' C4' C5' 112.2(6) no
C4' C5' C6' 113.7(8) no
C5' C6' C7' 112.6(8) no
C6' C7' C8' 112.7(7) no
C7' C8' C9' 113.4(8) no
C8' C9' C4' 112.9(7) no
C15 C10 N1 105.6(6) yes
C11 C10 N1 113.0(6) yes
C15 C10 C11 105.2(6) no
C10 C11 C12 104.7(7) no
C11 C12 C13 105.0(8) no
C12 C13 C14 103.7(7) no
C13 C14 C15 108.2(8) no
C14 C15 C10 107.8(7) no
C11' C10' N1 109.4(6) yes
C15' C10' N1 121.7(7) yes
C11' C10' C15' 121.6(7) no
C10' C11' C12' 112.5(7) no
C11' C12' C13' 114.7(9) no
C12' C13' C14' 117.3(8) no
C13' C14' C15' 115.2(8) no
C14' C15' C10' 113.8(8) no
C17 C16 N2 108.8(2) yes
C21 C16 N2 112.6(2) yes
C17 C16 C21 111.0(2) no
C16 C17 C18 111.1(2) no
C17 C18 C19 111.6(2) no
C18 C19 C20 111.1(2) no
C19 C20 C21 111.6(2) no
C16 C21 C20 109.9(2) no
C23 C22 N2 108.6(2) yes
C27 C22 N2 112.2(2) yes
C23 C22 C27 110.8(2) no
C22 C23 C24 110.3(2) no
C23 C24 C25 111.8(2) no
C24 C25 C26 111.6(2) no
C25 C26 C27 111.2(2) no
C26 C27 C22 109.9(2) 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
S1 C2 . 1.789(2) yes
S1 C3 . 1.770(2) yes
S2 C3 . 1.667(2) yes
O1 C1 . 1.252(3) yes
O2 C1 . 1.240(3) yes
N1 C3 . 1.338(3) yes
N1 C4 . 1.464(6) yes
N1 C10 . 1.538(6) yes
N1 C4' . 1.539(6) yes
N1 C10' . 1.442(6) yes
N2 C16 . 1.501(2) yes
N2 C22 . 1.501(3) yes
C1 C2 . 1.514(3) no
C4 C5 . 1.529(8) no
C4 C9 . 1.535(7) no
C5 C6 . 1.541(8) no
C6 C7 . 1.526(8) no
C7 C8 . 1.538(8) no
C8 C9 . 1.546(8) no
C4' C9' . 1.515(7) no
C4' C5' . 1.520(8) no
C5' C6' . 1.529(8) no
C6' C7' . 1.509(8) no
C7' C8' . 1.517(9) no
C8' C9' . 1.525(8) no
C10 C15 . 1.536(8) no
C10 C11 . 1.557(8) no
C11 C12 . 1.567(9) no
C12 C13 . 1.535(9) no
C13 C14 . 1.542(8) no
C14 C15 . 1.548(8) no
C10' C11' . 1.485(7) no
C10' C15' . 1.494(8) no
C11' C12' . 1.529(9) no
C12' C13' . 1.492(9) no
C13' C14' . 1.506(9) no
C14' C15' . 1.521(8) no
C16 C17 . 1.509(3) no
C16 C21 . 1.515(3) no
C17 C18 . 1.532(3) no
C18 C19 . 1.508(4) no
C19 C20 . 1.513(4) no
C20 C21 . 1.520(3) no
C22 C23 . 1.516(3) no
C22 C27 . 1.519(3) no
C23 C24 . 1.526(3) no
C24 C25 . 1.514(3) no
C25 C26 . 1.516(3) no
C26 C27 . 1.518(3) no
N2 O1 . 2.706(2) yes
N2 O2 3_657 2.757(2) yes
