#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025484.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025484
loop_
_publ_author_name
'Ali Rostami'
'Alexis Colin'
'Xiao Yu Li'
'Michael G. Chudzinski'
'Alan J. Lough'
'Mark S. Taylor'
_publ_section_title
;
 N,N'-Diarylsquaramides: General, High-Yielding Synthesis and Applications
 in Colorimetric Anion Sensing
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3983
_journal_page_last               3992
_journal_paper_doi               10.1021/jo100104g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H20 N2 O2, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H32 N2 O4 S2'
_chemical_formula_weight         476.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.400(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.9867(5)
_cell_length_b                   18.6517(15)
_cell_length_c                   13.5460(12)
_cell_measurement_reflns_used    6137
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     1249.4(2)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.1513
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6137
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(15)
_refine_ls_extinction_coef       none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                2142
_reflns_number_total             3909
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100104g_si_002.cif
_cod_data_source_block           1i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025484
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5448(10) 0.5281(3) 0.4553(3) 0.0470(13) Uani 1 1 d . . .
O2 O 0.3438(10) 0.5738(3) 0.6626(4) 0.0460(13) Uani 1 1 d . . .
N1 N 0.4841(12) 0.6986(4) 0.3780(4) 0.0361(15) Uani 1 1 d . . .
H1N H 0.415(13) 0.746(4) 0.375(5) 0.05(2) Uiso 1 1 d . . .
N2 N 0.3085(12) 0.7448(4) 0.5850(4) 0.0370(14) Uani 1 1 d . . .
H2N H 0.324(16) 0.785(5) 0.535(6) 0.09(3) Uiso 1 1 d . . .
C1 C 0.3836(13) 0.6057(4) 0.5870(5) 0.0379(17) Uani 1 1 d . . .
C2 C 0.4762(14) 0.5843(4) 0.4900(5) 0.0339(17) Uani 1 1 d . . .
C3 C 0.3628(13) 0.6797(4) 0.5498(5) 0.0330(17) Uani 1 1 d . . .
C4 C 0.4517(13) 0.6604(4) 0.4591(5) 0.0322(17) Uani 1 1 d . . .
C5 C 0.5846(13) 0.6709(4) 0.2917(5) 0.0354(17) Uani 1 1 d . . .
C6 C 0.7763(13) 0.6172(4) 0.2995(5) 0.0326(17) Uani 1 1 d . . .
H6A H 0.8470 0.6000 0.3636 0.039 Uiso 1 1 calc R . .
C7 C 0.8691(13) 0.5875(4) 0.2154(5) 0.0349(17) Uani 1 1 d . . .
C8 C 0.7585(15) 0.6138(4) 0.1230(6) 0.0458(19) Uani 1 1 d . . .
H8A H 0.8143 0.5939 0.0644 0.055 Uiso 1 1 calc R . .
C9 C 0.5689(14) 0.6682(4) 0.1149(5) 0.0398(18) Uani 1 1 d . . .
H9A H 0.5027 0.6862 0.0508 0.048 Uiso 1 1 calc R . .
C10 C 0.4723(14) 0.6972(4) 0.1982(5) 0.0358(17) Uani 1 1 d . . .
C11 C 0.2562(15) 0.7544(4) 0.1866(5) 0.0452(19) Uani 1 1 d . . .
H11A H 0.1017 0.7386 0.2191 0.068 Uiso 1 1 calc R . .
H11B H 0.1972 0.7627 0.1157 0.068 Uiso 1 1 calc R . .
H11C H 0.3294 0.7990 0.2176 0.068 Uiso 1 1 calc R . .
C12 C 1.0737(14) 0.5276(4) 0.2259(5) 0.0464(19) Uani 1 1 d . . .
H12A H 1.1995 0.5338 0.1766 0.070 Uiso 1 1 calc R . .
H12B H 0.9804 0.4815 0.2150 0.070 Uiso 1 1 calc R . .
H12C H 1.1743 0.5286 0.2930 0.070 Uiso 1 1 calc R . .
C13 C 0.2054(13) 0.7574(4) 0.6783(5) 0.0314(16) Uani 1 1 d . . .
C14 C 0.0314(13) 0.7095(4) 0.7134(5) 0.0330(17) Uani 1 1 d . . .
H14A H -0.0269 0.6686 0.6745 0.040 Uiso 1 1 calc R . .
C15 C -0.0607(13) 0.7195(4) 0.8044(5) 0.0378(18) Uani 1 1 d . . .
C16 C 0.0306(14) 0.7809(5) 0.8574(5) 0.046(2) Uani 1 1 d . . .
H16A H -0.0278 0.7892 0.9205 0.055 Uiso 1 1 calc R . .
C17 C 0.2008(14) 0.8297(4) 0.8225(5) 0.0417(19) Uani 1 1 d . . .
H17A H 0.2543 0.8712 0.8608 0.050 Uiso 1 1 calc R . .
C18 C 0.2966(13) 0.8191(4) 0.7309(5) 0.0367(17) Uani 1 1 d . . .
C19 C -0.2549(14) 0.6685(4) 0.8440(5) 0.0428(19) Uani 1 1 d . . .
H19A H -0.2633 0.6239 0.8055 0.064 Uiso 1 1 calc R . .
H19B H -0.4351 0.6903 0.8380 0.064 Uiso 1 1 calc R . .
H19C H -0.1929 0.6581 0.9141 0.064 Uiso 1 1 calc R . .
C20 C 0.4962(14) 0.8703(4) 0.6943(5) 0.0481(19) Uani 1 1 d . . .
H20A H 0.4237 0.8881 0.6282 0.072 Uiso 1 1 calc R . .
H20B H 0.6675 0.8454 0.6904 0.072 Uiso 1 1 calc R . .
H20C H 0.5272 0.9108 0.7406 0.072 Uiso 1 1 calc R . .
S1 S 0.0410(4) 0.8743(2) 0.37826(14) 0.0430(5) Uani 1 1 d . . .
O3 O 0.3047(9) 0.8370(3) 0.4177(3) 0.0456(13) Uani 1 1 d . . .
C21 C -0.0805(16) 0.9128(5) 0.4846(6) 0.053(2) Uani 1 1 d . . .
H21A H -0.1126 0.8747 0.5315 0.080 Uiso 1 1 calc R . .
H21B H -0.2500 0.9384 0.4637 0.080 Uiso 1 1 calc R . .
H21C H 0.0542 0.9464 0.5169 0.080 Uiso 1 1 calc R . .
C22 C 0.1407(15) 0.9538(4) 0.3220(5) 0.050(2) Uani 1 1 d . . .
H22A H 0.2134 0.9419 0.2602 0.075 Uiso 1 1 calc R . .
H22B H 0.2800 0.9782 0.3676 0.075 Uiso 1 1 calc R . .
H22C H -0.0162 0.9855 0.3070 0.075 Uiso 1 1 calc R . .
S2 S 0.4415(4) 0.4553(2) 0.98182(19) 0.0467(9) Uani 0.817(6) 1 d PD A 1
O4 O 0.7267(12) 0.4543(6) 0.9597(7) 0.059(3) Uani 0.817(6) 1 d PD A 1
C23 C 0.2781(19) 0.3832(5) 0.9123(8) 0.055(3) Uani 0.817(6) 1 d PD A 1
H23A H 0.3112 0.3869 0.8427 0.083 Uiso 0.817(6) 1 calc PR A 1
H23B H 0.0831 0.3854 0.9157 0.083 Uiso 0.817(6) 1 calc PR A 1
H23C H 0.3498 0.3375 0.9401 0.083 Uiso 0.817(6) 1 calc PR A 1
C24 C 0.274(3) 0.5266(5) 0.9115(16) 0.047(2) Uani 0.817(6) 1 d PD A 1
H24A H 0.3461 0.5726 0.9380 0.071 Uiso 0.817(6) 1 calc PR A 1
H24B H 0.0796 0.5243 0.9163 0.071 Uiso 0.817(6) 1 calc PR A 1
H24C H 0.3037 0.5221 0.8417 0.071 Uiso 0.817(6) 1 calc PR A 1
S2A S 0.408(2) 0.4458(5) 0.8807(9) 0.057(5) Uani 0.183(6) 1 d PD A 2
O4A O 0.706(3) 0.451(3) 0.909(2) 0.065(15) Uani 0.183(6) 1 d PD A 2
C23A C 0.286(8) 0.395(2) 0.977(2) 0.055(3) Uani 0.183(6) 1 d PD A 2
H23D H 0.3701 0.3473 0.9801 0.083 Uiso 0.183(6) 1 calc PR A 2
H23E H 0.0892 0.3898 0.9624 0.083 Uiso 0.183(6) 1 calc PR A 2
H23F H 0.3317 0.4195 1.0406 0.083 Uiso 0.183(6) 1 calc PR A 2
C24A C 0.268(12) 0.5299(12) 0.909(6) 0.047(2) Uani 0.183(6) 1 d PD A 2
H24D H 0.4133 0.5622 0.9368 0.071 Uiso 0.183(6) 1 calc PR A 2
H24E H 0.1420 0.5228 0.9585 0.071 Uiso 0.183(6) 1 calc PR A 2
H24F H 0.1706 0.5508 0.8487 0.071 Uiso 0.183(6) 1 calc PR A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 125.0(6) . . ?
C3 N2 C13 124.6(6) . . ?
O2 C1 C3 137.2(6) . . ?
O2 C1 C2 134.8(6) . . ?
C3 C1 C2 88.0(5) . . ?
O1 C2 C4 137.3(6) . . ?
O1 C2 C1 134.5(6) . . ?
C4 C2 C1 88.2(5) . . ?
N2 C3 C4 129.9(6) . . ?
N2 C3 C1 137.3(6) . . ?
C4 C3 C1 92.5(5) . . ?
N1 C4 C3 132.0(6) . . ?
N1 C4 C2 136.7(6) . . ?
C3 C4 C2 91.2(5) . . ?
C6 C5 C10 121.0(6) . . ?
C6 C5 N1 120.9(6) . . ?
C10 C5 N1 118.1(6) . . ?
C5 C6 C7 121.6(6) . . ?
C8 C7 C6 117.3(6) . . ?
C8 C7 C12 122.1(6) . . ?
C6 C7 C12 120.5(6) . . ?
C9 C8 C7 121.3(7) . . ?
C8 C9 C10 121.7(7) . . ?
C9 C10 C5 117.0(6) . . ?
C9 C10 C11 120.5(6) . . ?
C5 C10 C11 122.5(6) . . ?
C14 C13 C18 122.6(6) . . ?
C14 C13 N2 120.7(6) . . ?
C18 C13 N2 116.8(5) . . ?
C13 C14 C15 121.2(7) . . ?
C14 C15 C16 116.5(6) . . ?
C14 C15 C19 122.3(6) . . ?
C16 C15 C19 121.2(6) . . ?
C17 C16 C15 122.9(6) . . ?
C16 C17 C18 120.6(6) . . ?
C13 C18 C17 116.2(6) . . ?
C13 C18 C20 122.7(6) . . ?
C17 C18 C20 121.1(6) . . ?
O3 S1 C22 104.9(3) . . ?
O3 S1 C21 105.6(3) . . ?
C22 S1 C21 98.9(4) . . ?
O4 S2 C23 105.5(5) . . ?
O4 S2 C24 107.2(5) . . ?
C23 S2 C24 97.5(7) . . ?
O4A S2A C23A 105.5(5) . . ?
O4A S2A C24A 107.2(6) . . ?
C23A S2A C24A 97.5(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.216(7) . ?
O2 C1 1.223(8) . ?
N1 C4 1.336(8) . ?
N1 C5 1.427(8) . ?
N2 C3 1.345(8) . ?
N2 C13 1.444(8) . ?
C1 C3 1.467(9) . ?
C1 C2 1.503(10) . ?
C2 C4 1.481(9) . ?
C3 C4 1.406(9) . ?
C5 C6 1.378(9) . ?
C5 C10 1.406(9) . ?
C6 C7 1.398(9) . ?
C7 C8 1.390(9) . ?
C7 C12 1.507(9) . ?
C8 C9 1.382(10) . ?
C9 C10 1.393(9) . ?
C10 C11 1.510(9) . ?
C13 C14 1.372(9) . ?
C13 C18 1.399(9) . ?
C14 C15 1.382(9) . ?
C15 C16 1.396(9) . ?
C15 C19 1.505(9) . ?
C16 C17 1.370(9) . ?
C17 C18 1.400(9) . ?
C18 C20 1.509(10) . ?
S1 O3 1.522(5) . ?
S1 C22 1.768(7) . ?
S1 C21 1.783(7) . ?
S2 O4 1.491(6) . ?
S2 C23 1.779(9) . ?
S2 C24 1.779(13) . ?
S2A O4A 1.491(7) . ?
S2A C23A 1.779(9) . ?
S2A C24A 1.780(13) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3 0.94(7) 1.91(8) 2.808(7) 160(6) .
N2 H2N O3 1.02(9) 1.86(9) 2.844(7) 162(7) .
