#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/41/2004146.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_2004146
loop_
_publ_author_name
'Sudha, L.'
'Senthil Selvan, J.'
'Subramanian, K.'
'Steiner, Th.'
'Koellner, G.'
'Srinivasan, N.'
'Ramdas, K.'
_publ_section_title
;
 1-(Morpholinothiocarbonyl)-3,3-(oxydiethyl)-1,2-diphenylguanidine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2323
_journal_page_last               2325
_journal_paper_doi               10.1107/S0108270195007165
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C22 H26 N4 O2 S'
_chemical_formula_sum            'C22 H26 N4 O2 S'
_chemical_formula_weight         410.5
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.928(3)
_cell_length_b                   14.999(2)
_cell_length_c                   18.952(2)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    294
_cell_measurement_theta_max      33
_cell_measurement_theta_min      16
_cell_volume                     4243.4(11)
_computing_data_collection       'SDP Frenz (1978)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3134
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        6.6
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.52
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.29
_exptl_crystal_density_meas      1.30
_exptl_crystal_density_method    'flotation in KI + water'
_exptl_crystal_description       needle
_exptl_crystal_size_max          1.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     366
_refine_ls_number_reflns         2041
_refine_ls_R_factor_obs          0.068
_refine_ls_shift/esd_max         0.008
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)+0.075614F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.073
_reflns_number_observed          2041
_reflns_number_total             2650
_reflns_observed_criterion       F>3\s(F)
_cod_data_source_file            ka1128.cif
_cod_data_source_block           ka1128a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' 1/[\s^2^(F)+0.075614F^2^]' 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^(F)+0.075614F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4243.50(10)
_cod_database_code               2004146
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,y,1/2-z
x,1/2-y,1/2+z
1/2-x,1/2+y,z
-x,-y,-z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
C(1) -0.0343(3) 0.2485(4) 0.4483(3) 3.3(2)
C(2) -0.0215(4) 0.2612(4) 0.3766(3) 4.0(2)
C(3) -0.0411(5) 0.1935(5) 0.3290(3) 4.7(2)
C(4) -0.0746(5) 0.1146(5) 0.3520(4) 0.4(2)
C(5) -0.0889(5) 0.1014(5) 0.4226(4) 5.3(2)
C(6) -0.0694(5) 0.1698(4) 0.4715(3) 4.5(2)
C(1') 0.1442(4) 0.2205(3) 0.5874(3) 3.1(1)
C(2') 0.0761(4) 0.1907(4) 0.6306(3) 4.0(2)
C(3') 0.0955(5) 0.1442(5) 0.6916(3) 4.7(2)
C(4') 0.1812(5) 0.1260(5) 0.7091(3) 4.8(2)
C(5') 0.2509(4) 0.1554(5) 0.6679(3) 4.6(2)
C(6') 0.2327(4) 0.2021(4) 0.6065(3) 4.1(2)
N(7) -0.0230(3) 0.3225(3) 0.4947(2) 3.4(1)
C(8) 0.0489(4) 0.3325(3) 0.5306(3) 2.9(1)
N(9) 0.1227(3) 0.2708(3) 0.5254(2) 3.0(1)
N(10) 0.0574(3) 0.3977(3) 0.5785(2) 3.4(1)
C(11) 0.1420(4) 0.4273(4) 0.6101(3) 4.0(2)
C(12) 0.1266(4) 0.4443(5) 0.6873(3) 4.8(2)
O(13) 0.0566(3) 0.5076(3) 0.6990(2) 4.9(1)
C(14) -0.0241(4) 0.4784(4) 0.6678(3) 4.5(2)
C(15) -0.0147(4) 0.4619(4) 0.5900(3) 3.6(1)
C(16) 0.1796(3) 0.2830(4) 0.4667(3) 3.2(2)
S(17) 0.1920(1) 0.3831(1) 0.4316(1) 4.0(1)
N(18) 0.2201(3) 0.2086(3) 0.4423(2) 3.7(1)
C(19) 0.1929(4) 0.1158(4) 0.4558(4) 4.3(2)
C(20) 0.1728(5) 0.0704(4) 0.3878(4) 5.0(2)
O(21) 0.2443(3) 0.0734(3) 0.3393(3) 5.4(2)
C(22) 0.2611(5) 0.1629(5) 0.3235(4) 5.2(2)
C(23) 0.2902(4) 0.2147(5) 0.3886(3) 4.3(2)
H(2) 0.017(5) 0.314(5) 0.356(4) 60(20)
H(3) -0.033(5) 0.209(4) 0.277(4) 86(20)
H(4) -0.089(4) 0.072(5) 0.316(4) 33(20)
H(5) -0.113(4) 0.049(5) 0.440(4) 59(19)
H(6) -0.089(4) 0.156(4) 0.517(3) 65(17)
H(2') 0.004(5) 0.200(4) 0.619(3) 76(19)
H(3') 0.047(5) 0.119(4) 0.719(3) 74(19)
H(4') 0.195(5) 0.092(5) 0.752(4) 61(20)
H(5') 0.313(5) 0.140(5) 0.684(4) 79(20)
H(6') 0.282(3) 0.221(3) 0.584(3) 53(15)
H(11)a 0.156(4) 0.483(5) 0.582(4) 81(19)
H(11)b 0.197(5) 0.386(5) 0.605(4) 33(20)
H(12)a 0.180(5) 0.445(5) 0.713(4) 89(20)
H(12)b 0.110(4) 0.382(4) 0.712(3) 79(17)
H(14)a -0.071(5) 0.516(5) 0.677(4) 61(20)
H(14)b -0.044(4) 0.423(4) 0.689(3) 93(17)
H(15)a -0.075(5) 0.436(4) 0.580(4) 64(20)
H(15)b 0.011(4) 0.516(5) 0.561(4) 48(20)
H(19)a 0.237(5) 0.092(5) 0.477(4) 36(20)
H(19)b 0.149(3) 0.117(3) 0.491(3) 63(15)
H(20)a 0.114(5) 0.095(5) 0.364(4) 63(20)
H(20)b 0.154(4) 0.024(4) 0.396(3) 87(16)
H(22)a 0.294(3) 0.188(3) 0.281(2) 119(13)
H(22)b 0.333(5) 0.163(5) 0.293(3) 82(19)
H(23)a 0.314(5) 0.281(5) 0.382(4) 76(20)
H(23)b 0.356(5) 0.187(4) 0.407(3) 75(19)
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) N(7) 121.3(5) yes
C(2) C(1) N(7) 118.8(5) yes
C(2) C(1) C(6) 119.2(5) yes
C(1) C(2) C(3) 120.5(6) yes
C(2) C(3) C(4) 120.4(6) yes
C(3) C(4) C(5) 119.8(7) yes
C(4) C(5) C(6) 120.3(7) yes
C(1) C(6) C(5) 119.7(6) yes
C(6') C(1') N(9) 121.9(5) yes
C(2') C(1') N(9) 119.5(5) yes
C(2') C(1') C(6') 118.6(5) yes
C(1') C(2') C(3') 120.4(6) yes
C(2') C(3') C(4') 120.5(6) yes
C(3') C(4') C(5') 120.9(6) yes
C(4') C(5') C(6') 119.4(6) yes
C(1') C(6') C(5') 120.2(5) yes
C(1) N(7) C(8) 121.2(4) yes
N(7) C(8) N(10) 121.7(5) yes
N(7) C(8) N(9) 122.0(5) yes
N(9) C(8) N(10) 116.2(5) yes
C(1') N(9) C(8) 116.9(4) yes
C(8) N(9) C(16) 115.5(4) yes
C(1') N(9) C(16) 125.4(4) yes
C(8) N(10) C(15) 120.8(5) yes
C(8) N(10) C(11) 125.4(5) yes
C(11) N(10) C(15) 112.0(4) yes
N(10) C(11) C(12) 108.5(5) yes
C(11) C(12) O(13) 112.1(5) yes
C(12) O(13) C(14) 110.7(5) yes
O(13) C(14) C(15) 112.5(5) yes
N(10) C(15) C(14) 108.9(5) yes
N(9) C(16) N(18) 115.6(5) yes
N(9) C(16) S(17) 120.2(4) yes
S(17) C(16) N(18) 124.2(4) yes
C(16) N(18) C(23) 120.5(5) yes
C(16) N(18) C(19) 126.7(5) yes
C(19) N(18) C(23) 112.2(5) yes
N(18) C(19) C(20) 109.7(5) yes
C(19) C(20) O(21) 113.4(6) yes
C(20) O(21) C(22) 107.8(5) yes
O(21) C(22) C(23) 111.6(6) yes
N(18) C(23) C(22) 109.2(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.385(8) yes
C(1) C(6) 1.364(9) yes
C(1) N(7) 1.426(7) yes
C(2) C(3) 1.389(9) yes
C(3) C(4) 1.357(11) yes
C(4) C(5) 1.369(11) yes
C(5) C(6) 1.413(10) yes
C(1') C(2') 1.380(8) yes
C(1') C(6') 1.397(8) yes
C(1') N(9) 1.433(7) yes
C(2') C(3') 1.381(9) yes
C(3') C(4') 1.350(10) yes
C(4') C(5') 1.374(9) yes
C(5') C(6') 1.385(9) yes
N(7) C(8) 1.280(7) yes
C(8) N(9) 1.442(7) yes
C(8) N(10) 1.340(7) yes
N(9) C(16) 1.412(7) yes
N(10) C(11) 1.467(7) yes
N(10) C(15) 1.461(8) yes
C(11) C(12) 1.503(8) yes
C(12) O(13) 1.429(8) yes
O(13) C(14) 1.412(7) yes
C(14) C(15) 1.502(8) yes
C(16) S(17) 1.653(6) yes
C(16) N(18) 1.351(7) yes
N(18) C(19) 1.472(8) yes
N(18) C(23) 1.463(7) yes
C(19) C(20) 1.488(10) yes
C(20) O(21) 1.409(9) yes
O(21) C(22) 1.398(9) yes
C(22) C(23) 1.521(10) yes
C(2) H(2) 1.06(7) no
C(3) H(3) 1.02(7) no
C(4) H(4) 0.96(7) no
C(5) H(5) 0.93(7) no
C(6) H(6) 0.94(6) no
C(2') H(2') 1.11(7) no
C(3') H(3') 0.97(7) no
C(3') H(3') 0.97(7) no
C(4') H(4') 0.98(7) no
C(5') H(5') 1.00(7) no
C(6') H(6') 0.90(5) no
C(11) H(11)a 1.00(7) no
C(11) H(11)b 1.03(7) no
C(12) H(12)a 0.93(7) no
C(12) H(12)b 1.08(6) no
C(14) H(14)a 0.92(7) no
C(14) H(14)b 0.97(6) no
C(15) H(15)a 1.00(7) no
C(15) H(15)b 1.04(7) no
C(19) H(19)a 0.85(7) no
C(19) H(19)b 0.94(5) no
C(19) H(19)b 0.94(5) no
C(20) H(20)a 1.05(7) no
C(20) H(20)b 0.77(6) no
C(22) H(22)a 1.02(5) no
C(22) H(22)b 1.21(7) no
C(23) H(23)a 1.12(5) no
C(23) H(23)b 1.06(5) 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(7) C(8) -100.8(6) yes
C(6) C(1) N(7) C(8) 88.6(7) yes
C(1) N(7) C(8) N(9) 1.0(8) yes
C(1) N(7) C(8) N(10) -174.6(5) yes
N(7) C(8) N(9) C(1') -115.2(6) yes
N(10) C(8) N(9) C(1') 60.6(6) yes
C(8) N(9) C(1') C(2') 37.2(7) yes
C(8) N(9) C(1') C(6') -141.5(5) yes
N(7) C(8) N(10) C(11) -165.2(5) yes
N(7) C(8) N(10) C(15) -1.9(8) yes
N(9) C(8) N(10) C(11) 19.0(8) yes
N(9) C(8) N(10) C(15) -177.7(5) yes
C(8) N(9) C(16) S(17) 28.5(6) yes
C(1') N(9) C(16) S(17) -134.3(5) yes
C(8) N(9) C(16) N(18) -150.6(5) yes
C(1') N(9) C(16) N(18) 46.6(7) yes
N(9) C(16) N(18) C(19) 18.9(8) yes
N(9) C(16) N(18) C(23) -171.1(5) yes
S(17) C(16) N(18) C(19) -160.2(5) yes
S(17) C(16) N(18) C(23) 9.9(7) yes
