#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/52/2005262.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_2005262
loop_
_publ_author_name
'Sudha, L.'
'Selvan, J. S.'
'Subramanian, K.'
'Steiner, Th.'
'Koellner, G.'
'Srinivasan, N.'
'Ramdas, K.'
_publ_section_title
;
 1,3-Bis(2-methylphenyl)-2-(4-morpholino)isothiourea
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2047
_journal_page_last               2049
_journal_paper_doi               10.1107/S0108270196002429
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C19 H23 N3 O1 S1'
_chemical_formula_sum            'C19 H23 N3 O S'
_chemical_formula_weight         341.5
_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'
_atom_type_scat_source           'SHELXL93 (Sheldrick, 1993)'
_cell_angle_alpha                90
_cell_angle_beta                 112.32(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.773(3)
_cell_length_b                   11.408(1)
_cell_length_c                   14.830(3)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    298
_cell_measurement_theta_max      48
_cell_measurement_theta_min      22
_cell_volume                     1842.5(7)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2850
_diffrn_reflns_theta_max         59.9
_diffrn_standards_decay_%        12
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.63
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_meas      1.25
_exptl_crystal_density_method    'flotation in KI/water solution'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.138
_refine_ls_goodness_of_fit_obs   1.138
_refine_ls_hydrogen_treatment    refU
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2727
_refine_ls_R_factor_obs          0.058
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
w = 1/[\s^2^(F~o~^2^) + (0.0932P)^2^ + 0.1615P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.175
_refine_ls_wR_factor_obs         0.141
_reflns_number_observed          2683
_reflns_number_total             2727
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ka1178.cif
_cod_data_source_block           ka1178a
_cod_original_cell_volume        1842.5(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C19 H23 N3 O1 S1'
_cod_database_code               2005262
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C(1) .8613(2) .3683(2) .6590(2) .056(1)
C(2) .9520(2) .3783(2) .6200(2) .060(1)
C(3) 1.0033(3) .4880(2) .6200(2) .070(1)
C(4) .9662(3) .5859(3) .6556(2) .077(1)
C(5) .8763(3) .5750(2) .6925(2) .077(1)
C(6) .8244(3) .4666(2) .6950(2) .069(1)
C(7) .9942(3) .2744(3) .5790(3) .075(1)
C(1') .6185(2) .2334(2) .7990(2) .062(1)
C(2') .4945(3) .2637(2) .7571(2) .072(1)
C(3') .4189(3) .2279(3) .8042(3) .085(1)
C(4') .4619(3) .1656(3) .8889(2) .086(1)
C(5') .5834(3) .1364(3) .9301(2) .087(1)
C(6') .6620(3) .1698(3) .8847(2) .076(1)
C(7') .4444(5) .3328(5) .6648(4) .108(1)
N(8) .8089(2) .2567(2) .6569(2) .062(1)
C(9) .7317(2) .2201(2) .6995(2) .059(1)
N(10) .7013(2) .2795(2) .7589(2) .071(1)
S(11) .6739(1) .0736(1) .6665(1) .065(1)
N(12) .7416(2) .0360(2) .5871(1) .060(1)
C(13) .6548(3) .0182(3) .4863(2) .074(1)
C(14) .7255(4) -.0037(3) .4221(2) .087(1)
O(15) .8054(2) -0.1011(2) .4542(2) .091(1)
C(16) .8893(3) -.0809(3) .5509(2) .083(1)
C(17) .8243(3) -.0658(3) .6195(2) .071(1)
H(3) 1.066(3) .497(2) .591(2) .080(8)
H(4) 1.004(3) .664(3) .655(2) .090(9)
H(5) .848(3) .643(3) .723(2) .087(9)
H(6) .770(3) .460(2) .721(2) .066(7)
H(71) 1.055(3) .291(3) .563(2) .087(9)
H(72) .922(3) .239(3) .517(3) .11(1)
H(73) 1.016(3) .210(3) .625(3) .10(1)
H(3') .336(4) .251(3) .778(3) .11(1)
H(4') .411(3) .146(3) .919(2) .090(9)
H(5') .613(3) .092(3) .986(2) .09(1)
H(6') .749(3) .150(3) .914(2) .081(9)
H(7'1) .466(5) .300(5) .610(4) .15(2)
H(7'2) .495(5) .403(5) .667(4) .16(2)
H(7'3) .370(5) .351(4) .642(3) .14(2)
H(8) .821(2) .211(2) .618(2) .054(7)
H(131) .601(3) .089(3) .463(2) .077(8)
H(132) .606(3) -.047(3) .483(2) .09(1)
H(141) .669(3) -.019(3) .359(3) .10(1)
H(142) .772(3) .068(3) .416(2) .10(1)
H(161) .936(3) -.004(4) .553(3) .11(1)
H(162) .940(3) -0.150(3) .571(2) .10(1)
H(171) .775(2) -0.138(3) .620(2) .072(7)
H(172) .880(3) -.052(3) .685(2) .086(9)
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
C(6) C(1) C(2) 119.7(2) yes
C(6) C(1) N(8) 122.8(2) yes
C(2) C(1) N(8) 117.4(2) yes
C(3) C(2) C(1) 118.2(2) yes
C(3) C(2) C(7) 120.1(2) yes
C(1) C(2) C(7) 121.7(2) yes
C(4) C(3) C(2) 122.0(3) yes
C(5) C(4) C(3) 119.1(3) yes
C(4) C(5) C(6) 120.4(3) yes
C(1) C(6) C(5) 120.5(3) yes
C(6') C(1') C(2') 119.9(2) yes
C(6') C(1') N(10) 120.4(2) yes
C(2') C(1') N(10) 119.3(2) yes
C(3') C(2') C(1') 117.8(3) yes
C(3') C(2') C(7') 120.8(3) yes
C(1') C(2') C(7') 121.4(3) yes
C(4') C(3') C(2') 122.3(3) yes
C(3') C(4') C(5') 119.9(3) yes
C(4') C(5') C(6') 119.6(3) yes
C(1') C(6') C(5') 120.5(3) yes
C(9) N(8) C(1) 129.3(2) yes
N(10) C(9) N(8) 125.2(2) yes
N(10) C(9) S(11) 120.6(2) yes
N(8) C(9) S(11) 114.2(2) yes
C(9) N(10) C(1') 120.9(2) yes
N(12) S(11) C(9) 101.20(10) yes
C(13) N(12) C(17) 109.9(2) yes
C(13) N(12) S(11) 114.2(2) yes
C(17) N(12) S(11) 113.4(2) yes
N(12) C(13) C(14) 109.2(3) yes
O(15) C(14) C(13) 112.0(3) yes
C(14) O(15) C(16) 109.4(2) yes
O(15) C(16) C(17) 111.5(3) yes
N(12) C(17) C(16) 108.4(2) yes
C(4) C(3) H(3) 119(2) no
C(2) C(3) H(3) 119(2) no
C(5) C(4) H(4) 120(2) no
C(3) C(4) H(4) 121(2) no
C(4) C(5) H(5) 123(2) no
C(6) C(5) H(5) 117(2) no
C(1) C(6) H(6) 120(2) no
C(5) C(6) H(6) 120(2) no
C(2) C(7) H(71) 112(2) no
C(2) C(7) H(72) 112(2) no
H(71) C(7) H(72) 108(3) no
C(2) C(7) H(73) 111(2) no
H(71) C(7) H(73) 110(3) no
H(72) C(7) H(73) 103(3) no
C(4') C(3') H(3') 120(2) no
C(2') C(3') H(3') 118(2) no
C(3') C(4') H(4') 120(2) no
C(5') C(4') H(4') 120(2) no
C(4') C(5') H(5') 121(2) no
C(6') C(5') H(5') 120(2) no
C(1') C(6') H(6') 119(2) no
C(5') C(6') H(6') 120(2) no
C(2') C(7') H(7'1) 114(3) no
C(2') C(7') H(7'2) 112(3) no
H(7'1) C(7') H(7'2) 90(4) no
C(2') C(7') H(7'3) 119(3) no
H(7'1) C(7') H(7'3) 108(4) no
H(7'2) C(7') H(7'3) 110(4) no
C(9) N(8) H(8) 117(2) no
C(1) N(8) H(8) 113(2) no
N(12) C(13) H(131) 110(2) no
C(14) C(13) H(131) 110(2) no
N(12) C(13) H(132) 110(2) no
C(14) C(13) H(132) 109(2) no
H(131) C(13) H(132) 109(3) no
O(15) C(14) H(141) 109(2) no
C(13) C(14) H(141) 108(2) no
O(15) C(14) H(142) 110(2) no
C(13) C(14) H(142) 112(2) no
H(141) C(14) H(142) 105(3) no
O(15) C(16) H(161) 109(2) no
C(17) C(16) H(161) 107(2) no
O(15) C(16) H(162) 107(2) no
C(17) C(16) H(162) 108(2) no
H(161) C(16) H(162) 115(3) no
N(12) C(17) H(171) 109(2) no
C(16) C(17) H(171) 111(2) no
N(12) C(17) H(172) 108(2) no
C(16) C(17) H(172) 112(2) no
H(171) C(17) H(172) 107(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(6) 1.381(4) yes
C(1) C(2) 1.399(3) yes
C(1) N(8) 1.410(3) yes
C(2) C(3) 1.389(4) yes
C(2) C(7) 1.501(4) yes
C(3) C(4) 1.375(4) yes
C(4) C(5) 1.370(4) yes
C(5) C(6) 1.387(4) yes
C(1') C(6') 1.382(4) yes
C(1') C(2') 1.396(4) yes
C(1') N(10) 1.421(3) yes
C(2') C(3') 1.385(4) yes
C(2') C(7') 1.494(5) yes
C(3') C(4') 1.363(5) yes
C(4') C(5') 1.367(5) yes
C(5') C(6') 1.388(4) yes
N(8) C(9) 1.355(3) yes
C(9) N(10) 1.267(3) yes
C(9) S(11) 1.801(3) yes
S(11) N(12) 1.708(2) yes
N(12) C(13) 1.470(4) yes
N(12) C(17) 1.473(3) yes
C(13) C(14) 1.504(4) yes
C(14) O(15) 1.416(4) yes
O(15) C(16) 1.418(4) yes
C(16) C(17) 1.497(4) yes
C(3) H(3) .99(3) no
C(4) H(4) 1.00(3) no
C(5) H(5) 1.01(3) no
C(6) H(6) .88(3) no
C(7) H(71) .85(3) no
C(7) H(72) 1.07(4) no
C(7) H(73) .97(4) no
C(3') H(3') .95(4) no
C(4') H(4') .90(3) no
C(5') H(5') .92(3) no
C(6') H(6') .97(3) no
C(7') H(7'1) 1.01(5) no
C(7') H(7'2) .99(6) no
C(7') H(7'3) .84(5) no
N(8) H(8) .83(3) no
C(13) H(131) 1.00(3) no
C(13) H(132) .93(4) no
C(14) H(141) .94(4) no
C(14) H(142) 1.01(4) no
C(16) H(161) 1.03(4) no
C(16) H(162) .96(4) no
C(17) H(171) 1.01(3) no
C(17) H(172) .95(3) no
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
_geom_torsion_publ_flag
C(2) C(1) N(8) C(9) 171.1(2) yes
C(6) C(1) N(8) C(9) -10.6(4) yes
C(1) N(8) C(9) N(10) -7.5(4) yes
C(1) N(8) C(9) S(11) 173.4(2) yes
N(8) C(9) N(10) C(1') 179.4(2) yes
N(8) C(9) S(11) N(12) -1.0(2) yes
C(9) N(10) C(1') C(2') -97.4(3) yes
C(9) N(10) C(1') C(6') 89.6(3) yes
C(9) S(11) N(12) C(13) -114.4(2) yes
C(9) S(11) N(12) C(17) 118.6(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055099
