#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/45/2004524.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_2004524
loop_
_publ_author_name
'Ramnathan, A.'
'Sivakumar, K.'
'Janarthanan, N.'
'Meerarani, D.'
'Ramadas, K.'
'Fun, H.-K.'
_publ_section_title
;
 Unsymmetrically Substituted Thioureas.
 1,1-Dimethyl-3-o-tolylthiourea and
 1,1-Diethyl-3-o-tolylthiourea
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              411
_journal_page_last               414
_journal_paper_doi               10.1107/S0108270195010778
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C12 H18 N2 S1'
_chemical_formula_sum            'C12 H18 N2 S'
_chemical_formula_weight         222.34
_chemical_name_systematic
;
1-Diethyl-3-tolyl thiourea.
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4360(10)
_cell_length_b                   8.4880(10)
_cell_length_c                   17.419(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      8
_cell_volume                     1247.3(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material
'SHELXL93. Geometric calculations: PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2226
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       needles
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983) parameter = -0.11(8)'
_refine_ls_abs_structure_Flack   -0.11(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.048
_refine_ls_goodness_of_fit_obs   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_restrained_S_obs      1.068
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_obs          0.0291
_refine_ls_shift/esd_max         0.000
_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^) + (0.0518P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0792
_refine_ls_wR_factor_obs         0.0774
_reflns_number_observed          1892
_reflns_number_total             2039
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            mu1206.cif
_cod_data_source_block           DETTU
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (19
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C12 H18 N2 S1'
_cod_database_code               2004524
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0287(2) 0.0387(2) 0.0296(2) 0.0028(2) 0.0063(2) -0.0011(2)
N1 0.0269(6) 0.0492(8) 0.0217(6) 0.0086(7) 0.0001(5) -0.0035(6)
N2 0.0274(7) 0.0367(7) 0.0226(6) -0.0007(6) 0.0000(5) -0.0009(5)
C1 0.0244(7) 0.0342(7) 0.0225(6) -0.0023(7) 0.0047(6) 0.0027(6)
C2 0.0343(8) 0.0420(9) 0.0224(7) 0.0093(7) -0.0028(6) -0.0039(6)
C3 0.0331(9) 0.0636(12) 0.0346(9) 0.0077(9) -0.0021(7) -0.0077(9)
C4 0.0379(10) 0.0757(15) 0.0543(12) 0.0167(11) -0.0144(10) -0.0231(12)
C5 0.0644(13) 0.0560(12) 0.0423(10) 0.0253(12) -0.0270(11) -0.0179(9)
C6 0.083(2) 0.0411(9) 0.0254(8) 0.0191(12) -0.0095(11) -0.0038(7)
C7 0.0533(10) 0.0373(8) 0.0243(7) 0.0081(8) -0.0002(8) -0.0047(7)
C8 0.0670(14) 0.0497(11) 0.0348(9) -0.0064(12) 0.0097(10) 0.0021(9)
C9 0.0373(9) 0.0414(9) 0.0247(7) -0.0050(8) -0.0002(7) -0.0038(7)
C10 0.0534(12) 0.0521(12) 0.0254(8) -0.0003(10) 0.0088(8) 0.0000(8)
C11 0.0295(8) 0.0464(9) 0.0298(8) 0.0047(7) -0.0025(7) -0.0008(7)
C12 0.0297(10) 0.084(2) 0.0594(14) -0.0020(11) 0.0115(10) 0.0010(14)
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_type_symbol
S 1 .17870(5) .01745(5) .66497(2) .03234(12) Uani d S
N1 1 .0119(2) .2102(2) .75544(8) .0326(3) Uani d N
N2 1 -.0989(2) .1615(2) .63799(7) .0289(3) Uani d N
C1 1 .0218(2) .1353(2) .68674(8) .0270(3) Uani d C
C2 1 .1203(2) .1948(2) .81824(9) .0329(4) Uani d C
C3 1 .2730(2) .2522(3) .81227(11) .0438(5) Uani d C
C4 1 .3746(3) .2436(3) .87460(14) .0559(6) Uani d C
C5 1 .3206(3) .1802(3) .94295(12) .0542(6) Uani d C
C6 1 .1690(3) .1259(2) .94869(10) .0497(5) Uani d C
C7 1 .0633(3) .1303(2) .88655(9) .0383(4) Uani d C
C8 1 -0.1016(3) .0665(3) .89237(13) .0505(5) Uani d C
C9 1 -0.1112(2) .0771(2) .56451(10) .0344(4) Uani d C
C10 1 -.0462(3) .1711(3) .49793(11) .0436(5) Uani d C
C11 1 -0.2299(2) .2700(2) .65445(10) .0352(4) Uani d C
C12 1 -0.3668(3) .1924(4) .6958(2) .0578(6) Uani d C
H1 1 -.074(3) .269(3) .7679(12) .038(5) Uiso d H
H3 1 .304(3) .301(3) .7651(12) .048(6) Uiso d H
H4 1 .478(3) .278(3) .8714(15) .064(8) Uiso d H
H5 1 .390(4) .183(3) .9859(16) .079(9) Uiso d H
H6 1 .137(3) .084(3) .9937(15) .062(7) Uiso d H
H8A 1 -0.114(4) -.004(3) .8574(18) .079(9) Uiso d H
H8B 1 -0.185(3) .148(3) .8853(12) .042(5) Uiso d H
H8C 1 -0.113(4) .013(3) .9367(19) .078(8) Uiso d H
H9A 1 -.062(3) -.023(2) .5692(12) .036(5) Uiso d H
H9B 1 -0.226(2) .051(2) .5588(11) .036(5) Uiso d H
H10A 1 -.059(3) .117(3) .4511(15) .055(7) Uiso d H
H10B 1 .072(3) .194(3) .5046(13) .046(6) Uiso d H
H10C 1 -0.106(3) .269(3) .4920(14) .053(7) Uiso d H
H11A 1 -0.260(3) .315(3) .6039(13) .052(6) Uiso d H
H11B 1 -0.192(2) .362(2) .6844(10) .030(4) Uiso d H
H12A 1 -0.407(4) .116(4) .6721(18) .081(10) Uiso d H
H12B 1 -0.331(3) .149(3) .7450(14) .062(7) Uiso d H
H12C 1 -0.446(4) .272(4) .7029(14) .068(8) Uiso d 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'
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 N1 C2 126.24(14) yes
C1 N2 C11 123.43(13) yes
C1 N2 C9 121.51(14) yes
C11 N2 C9 115.02(13) yes
N2 C1 N1 115.63(14) yes
N2 C1 S 123.07(12) yes
N1 C1 S 121.30(12) yes
C3 C2 C7 121.6(2) yes
C3 C2 N1 120.4(2) yes
C7 C2 N1 117.9(2) yes
C2 C3 C4 120.0(2) yes
C5 C4 C3 119.4(2) yes
C6 C5 C4 120.2(2) yes
C5 C6 C7 122.1(2) yes
C2 C7 C6 116.7(2) yes
C2 C7 C8 121.3(2) yes
C6 C7 C8 121.9(2) yes
N2 C9 C10 112.69(15) yes
N2 C11 C12 113.3(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 1.702(2) yes
N1 C1 1.358(2) yes
N1 C2 1.432(2) yes
N2 C1 1.344(2) yes
N2 C11 1.467(2) yes
N2 C9 1.470(2) yes
C2 C3 1.381(3) yes
C2 C7 1.395(2) yes
C3 C4 1.385(3) yes
C4 C5 1.384(4) yes
C5 C6 1.363(4) yes
C6 C7 1.403(3) yes
C7 C8 1.496(3) yes
C9 C10 1.511(3) yes
C11 C12 1.512(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12631486
