#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/70/2217073.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_2217073
loop_
_publ_author_name
'Huerta, Raúl'
'Castillo, Ivan'
'Hernández-Ortega, Simón'
_publ_section_title
;
 S-2-(Adamant-1-yl)-4-methylphenyl
 N,N-dimethylthiocarbamate
;
_journal_coeditor_code           GW2030
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o323
_journal_page_last               o323
_journal_paper_doi               10.1107/S1600536807066603
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H27 N O S'
_chemical_formula_moiety         'C20 H27 N O S'
_chemical_formula_sum            'C20 H27 N O S'
_chemical_formula_weight         329.49
_chemical_melting_point          .407E-305
_chemical_name_systematic
;
S-2-(Adamant-1-yl)-4-methylphenyl
N,N-dimethylthiocarbamate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.287(2)
_cell_angle_beta                 103.753(2)
_cell_angle_gamma                103.025(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6161(7)
_cell_length_b                   11.2113(12)
_cell_length_c                   13.2231(14)
_cell_measurement_reflns_used    3272
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.80
_cell_volume                     895.40(17)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7346
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0685P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2231
_reflns_number_total             3147
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2030.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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:

'_exptl_crystal_density_meas' value 'No' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        895.40(16)
_cod_original_sg_symbol_H-M      ' P -1'
_cod_database_code               2217073
_cod_database_fobs_code          2217073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S S 1.02047(9) 0.84253(6) 0.64328(4) 0.0637(2) Uani d . 1
O O 0.6891(3) 0.73897(17) 0.46508(13) 0.0809(5) Uani d . 1
N N 0.9990(3) 0.68642(18) 0.46352(15) 0.0678(5) Uani d . 1
C C1 0.8226(3) 0.91300(19) 0.67862(16) 0.0523(5) Uani d . 1
C C2 0.7344(3) 0.89238(17) 0.76267(15) 0.0445(5) Uani d . 1
C C3 0.6039(3) 0.96867(18) 0.78793(15) 0.0491(5) Uani d . 1
H H3 0.5447 0.9581 0.8439 0.059 Uiso calc R 1
C C4 0.5563(3) 1.05877(19) 0.73570(17) 0.0558(5) Uani d . 1
C C5 0.6397(4) 1.0725(2) 0.65162(19) 0.0686(6) Uani d . 1
H H5 0.6055 1.1298 0.6129 0.082 Uiso calc R 1
C C6 0.7731(4) 1.0025(2) 0.62444(18) 0.0677(6) Uani d . 1
H H6 0.8319 1.0149 0.5687 0.081 Uiso calc R 1
C C7 0.8757(3) 0.7468(2) 0.50903(17) 0.0569(5) Uani d . 1
C C8 1.2191(4) 0.6925(3) 0.5174(2) 0.0866(8) Uani d . 1
H H8A 1.2896 0.7743 0.5677 0.130 Uiso calc R 1
H H8B 1.2961 0.6794 0.4650 0.130 Uiso calc R 1
H H8C 1.2184 0.6278 0.5554 0.130 Uiso calc R 1
C C9 0.9060(5) 0.6114(3) 0.3519(2) 0.0997(9) Uani d . 1
H H9A 0.7529 0.6018 0.3295 0.150 Uiso calc R 1
H H9B 0.9300 0.5293 0.3457 0.150 Uiso calc R 1
H H9C 0.9739 0.6535 0.3068 0.150 Uiso calc R 1
C C10 0.7760(3) 0.79486(17) 0.82641(14) 0.0432(4) Uani d . 1
C C11 0.6436(3) 0.78732(18) 0.90815(16) 0.0500(5) Uani d . 1
H H11A 0.6802 0.8704 0.9578 0.060 Uiso calc R 1
H H11B 0.4900 0.7630 0.8697 0.060 Uiso calc R 1
C C12 0.6891(3) 0.69145(19) 0.97190(17) 0.0573(5) Uani d . 1
H H12 0.6023 0.6892 1.0225 0.069 Uiso calc R 1
C C13 0.6294(4) 0.56006(19) 0.89568(18) 0.0620(6) Uani d . 1
H H13A 0.4754 0.5325 0.8575 0.074 Uiso calc R 1
H H13B 0.6611 0.4999 0.9364 0.074 Uiso calc R 1
C C14 0.7607(3) 0.56505(19) 0.81512(16) 0.0577(6) Uani d . 1
H H14 0.7225 0.4807 0.7653 0.069 Uiso calc R 1
C C15 1.0029(4) 0.6065(2) 0.87625(18) 0.0619(6) Uani d . 1
H H15A 1.0364 0.5449 0.9149 0.074 Uiso calc R 1
H H15B 1.0871 0.6105 0.8255 0.074 Uiso calc R 1
C C16 1.0633(3) 0.73657(19) 0.95584(16) 0.0551(5) Uani d . 1
H H16 1.2181 0.7617 0.9956 0.066 Uiso calc R 1
C C17 1.0176(3) 0.83282(18) 0.89292(15) 0.0488(5) Uani d . 1
H H17A 1.1075 0.8383 0.8448 0.059 Uiso calc R 1
H H17B 1.0553 0.9158 0.9429 0.059 Uiso calc R 1
C C18 0.7109(3) 0.65985(18) 0.75146(15) 0.0511(5) Uani d . 1
H H18A 0.5569 0.6344 0.7136 0.061 Uiso calc R 1
H H18B 0.7894 0.6596 0.6981 0.061 Uiso calc R 1
C C19 0.9301(4) 0.7322(2) 1.03520(16) 0.0609(6) Uani d . 1
H H19A 0.9680 0.8153 1.0851 0.073 Uiso calc R 1
H H19B 0.9606 0.6724 1.0765 0.073 Uiso calc R 1
C C20 0.4196(4) 1.1399(2) 0.7697(2) 0.0765(7) Uani d . 1
H H20A 0.5108 1.2241 0.8080 0.115 Uiso calc R 1
H H20B 0.3458 1.1042 0.8159 0.115 Uiso calc R 1
H H20C 0.3148 1.1434 0.7070 0.115 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
_geom_angle_publ_flag
C1 S C7 101.66(10) yes
C7 N C8 124.42(19) yes
C7 N C9 118.09(19) yes
C8 N C9 117.48(19) yes
C6 C1 C2 120.18(19) ?
C6 C1 S 115.61(16) yes
C2 C1 S 123.90(15) yes
C3 C2 C1 115.62(18) ?
C3 C2 C10 120.07(17) ?
C1 C2 C10 124.31(16) ?
C4 C3 C2 124.62(19) ?
C4 C3 H3 117.7 ?
C2 C3 H3 117.7 ?
C5 C4 C3 117.73(19) ?
C5 C4 C20 120.8(2) ?
C3 C4 C20 121.5(2) ?
C6 C5 C4 120.4(2) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C1 121.3(2) ?
C5 C6 H6 119.3 ?
C1 C6 H6 119.3 ?
O C7 N 124.6(2) yes
O C7 S 123.20(17) yes
N C7 S 112.24(16) yes
N C8 H8A 109.5 ?
N C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
N C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N C9 H9A 109.5 ?
N C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
N C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C2 C10 C18 111.72(15) ?
C2 C10 C17 110.27(15) ?
C18 C10 C17 109.83(14) ?
C2 C10 C11 112.25(15) ?
C18 C10 C11 106.19(15) ?
C17 C10 C11 106.37(15) ?
C12 C11 C10 111.62(15) ?
C12 C11 H11A 109.3 ?
C10 C11 H11A 109.3 ?
C12 C11 H11B 109.3 ?
C10 C11 H11B 109.3 ?
H11A C11 H11B 108.0 ?
C13 C12 C11 110.19(18) ?
C13 C12 C19 109.73(17) ?
C11 C12 C19 109.23(16) ?
C13 C12 H12 109.2 ?
C11 C12 H12 109.2 ?
C19 C12 H12 109.2 ?
C12 C13 C14 108.95(17) ?
C12 C13 H13A 109.9 ?
C14 C13 H13A 109.9 ?
C12 C13 H13B 109.9 ?
C14 C13 H13B 109.9 ?
H13A C13 H13B 108.3 ?
C18 C14 C13 109.78(17) ?
C18 C14 C15 109.31(17) ?
C13 C14 C15 109.31(17) ?
C18 C14 H14 109.5 ?
C13 C14 H14 109.5 ?
C15 C14 H14 109.5 ?
C16 C15 C14 109.94(16) ?
C16 C15 H15A 109.7 ?
C14 C15 H15A 109.7 ?
C16 C15 H15B 109.7 ?
C14 C15 H15B 109.7 ?
H15A C15 H15B 108.2 ?
C19 C16 C17 109.52(17) ?
C19 C16 C15 110.29(18) ?
C17 C16 C15 108.77(16) ?
C19 C16 H16 109.4 ?
C17 C16 H16 109.4 ?
C15 C16 H16 109.4 ?
C16 C17 C10 111.20(15) ?
C16 C17 H17A 109.4 ?
C10 C17 H17A 109.4 ?
C16 C17 H17B 109.4 ?
C10 C17 H17B 109.4 ?
H17A C17 H17B 108.0 ?
C14 C18 C10 111.19(16) ?
C14 C18 H18A 109.4 ?
C10 C18 H18A 109.4 ?
C14 C18 H18B 109.4 ?
C10 C18 H18B 109.4 ?
H18A C18 H18B 108.0 ?
C16 C19 C12 108.76(16) ?
C16 C19 H19A 109.9 ?
C12 C19 H19A 109.9 ?
C16 C19 H19B 109.9 ?
C12 C19 H19B 109.9 ?
H19A C19 H19B 108.3 ?
C4 C20 H20A 109.5 ?
C4 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C4 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 1.780(2) yes
S C7 1.790(2) yes
O C7 1.209(2) yes
N C7 1.345(3) yes
N C8 1.441(3) yes
N C9 1.454(3) yes
C1 C6 1.395(3) ?
C1 C2 1.406(3) ?
C2 C3 1.395(3) ?
C2 C10 1.539(3) ?
C3 C4 1.382(3) ?
C3 H3 0.9300 ?
C4 C5 1.373(3) ?
C4 C20 1.500(3) ?
C5 C6 1.370(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 C18 1.541(3) ?
C10 C17 1.545(2) ?
C10 C11 1.548(2) ?
C11 C12 1.528(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.520(3) ?
C12 C19 1.530(3) ?
C12 H12 0.9800 ?
C13 C14 1.527(3) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 C18 1.524(3) ?
C14 C15 1.529(3) ?
C14 H14 0.9800 ?
C15 C16 1.527(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C19 1.523(3) ?
C16 C17 1.525(3) ?
C16 H16 0.9800 ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
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
C7 S C1 C6 -69.82(18)
C7 S C1 C2 116.52(17)
C6 C1 C2 C3 -1.7(3)
S C1 C2 C3 171.68(14)
C6 C1 C2 C10 179.12(18)
S C1 C2 C10 -7.5(3)
C1 C2 C3 C4 0.9(3)
C10 C2 C3 C4 -179.92(17)
C2 C3 C4 C5 1.3(3)
C2 C3 C4 C20 -178.19(19)
C3 C4 C5 C6 -2.8(3)
C20 C4 C5 C6 176.8(2)
C4 C5 C6 C1 2.0(4)
C2 C1 C6 C5 0.4(3)
S C1 C6 C5 -173.55(18)
C8 N C7 O -177.8(2)
C9 N C7 O 3.2(4)
C8 N C7 S 2.8(3)
C9 N C7 S -176.25(19)
C1 S C7 O -1.6(2)
C1 S C7 N 177.83(16)
C3 C2 C10 C18 124.16(18)
C1 C2 C10 C18 -56.7(2)
C3 C2 C10 C17 -113.39(18)
C1 C2 C10 C17 65.7(2)
C3 C2 C10 C11 5.0(2)
C1 C2 C10 C11 -175.85(17)
C2 C10 C11 C12 -179.21(15)
C18 C10 C11 C12 58.4(2)
C17 C10 C11 C12 -58.5(2)
C10 C11 C12 C13 -59.9(2)
C10 C11 C12 C19 60.7(2)
C11 C12 C13 C14 58.5(2)
C19 C12 C13 C14 -61.8(2)
C12 C13 C14 C18 -59.5(2)
C12 C13 C14 C15 60.4(2)
C18 C14 C15 C16 61.3(2)
C13 C14 C15 C16 -58.9(2)
C14 C15 C16 C19 58.6(2)
C14 C15 C16 C17 -61.5(2)
C19 C16 C17 C10 -61.6(2)
C15 C16 C17 C10 59.0(2)
C2 C10 C17 C16 -179.34(15)
C18 C10 C17 C16 -55.8(2)
C11 C10 C17 C16 58.72(19)
C13 C14 C18 C10 61.8(2)
C15 C14 C18 C10 -58.1(2)
C2 C10 C18 C14 177.91(15)
C17 C10 C18 C14 55.2(2)
C11 C10 C18 C14 -59.4(2)
C17 C16 C19 C12 60.7(2)
C15 C16 C19 C12 -59.0(2)
C13 C12 C19 C16 60.8(2)
C11 C12 C19 C16 -60.1(2)
