#------------------------------------------------------------------------------
#$Date: 2018-09-05 00:10:51 +0300 (Wed, 05 Sep 2018) $
#$Revision: 210433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/48/7104863.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_7104863
loop_
_publ_author_name
'Lam, Chi-Keung'
'Mak, Thomas C. W.'
_publ_section_title
;
 Carbonate and oxalate dianions as prolific hydrogen-bond acceptors in
 supramolecular assembly
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   21
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2660
_journal_page_last               2661
_journal_paper_doi               10.1039/b306649e
_journal_year                    2003
_chemical_formula_sum            'C24 H68 N16 O3 S7'
_chemical_formula_weight         853.36
_chemical_name_systematic
; 
 bis(tetraethylammonium) carbonate hepta-thiourea
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 124.009(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.462(4)
_cell_length_b                   12.901(2)
_cell_length_c                   17.355(3)
_cell_measurement_temperature    293(2)
_cell_volume                     4725.8(14)
_computing_cell_refinement       'SAINT-PLUS, Ver. 5.0, Bruker AXS, 1997.'
_computing_data_collection       'SMART for Windows NT, Bruker AXS, 1997.'
_computing_data_reduction        'SAINT-PLUS, Ver. 5.0, Bruker AXS, 1997.'
_computing_molecular_graphics    'XP-Interactive Molecular Graphics, Ver. 5.1'
_computing_publication_material  'SHELXTL-Bruker AXS, 1998.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Bruker_SMART_CCD_1K_area_detector
_diffrn_measurement_method       Omega_scan
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14020
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.774311
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.71
_exptl_crystal_size_min          0.61
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0511
_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)+(0.0938P)²+3.2263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                3592
_reflns_number_total             4656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b306649e.txt
_cod_data_source_block           Compound(1)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7104863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
S1 S 0.10440(3) -0.02087(6) 0.55997(5) 0.0664(2) Uani 1 1 d . . .
C1 C 0.07229(11) 0.02804(17) 0.45161(16) 0.0469(5) Uani 1 1 d . . .
N1 N 0.01011(10) 0.03213(17) 0.39020(14) 0.0573(5) Uani 1 1 d . . .
H1A H -0.0051 0.0563 0.3354 0.069 Uiso 1 1 calc R . .
H1B H -0.0150 0.0106 0.4052 0.069 Uiso 1 1 calc R . .
N2 N 0.10775(11) 0.0623(2) 0.42385(16) 0.0668(6) Uani 1 1 d . . .
H2A H 0.0903 0.0858 0.3683 0.080 Uiso 1 1 calc R . .
H2B H 0.1484 0.0612 0.4612 0.080 Uiso 1 1 calc R . .
S2 S -0.06195(5) 0.38336(6) 0.50084(6) 0.0780(3) Uani 1 1 d . . .
C2 C -0.05783(12) 0.34874(19) 0.40976(16) 0.0512(6) Uani 1 1 d . . .
N3 N -0.03643(11) 0.41318(17) 0.37434(15) 0.0596(6) Uani 1 1 d . . .
H3A H -0.0348 0.3941 0.3283 0.071 Uiso 1 1 calc R . .
H3B H -0.0241 0.4743 0.3973 0.071 Uiso 1 1 calc R . .
N4 N -0.07619(13) 0.25559(18) 0.37192(17) 0.0684(6) Uani 1 1 d . . .
H4B H -0.0739 0.2389 0.3259 0.082 Uiso 1 1 calc R . .
H4C H -0.0904 0.2117 0.3934 0.082 Uiso 1 1 calc R . .
S3 S 0.23991(3) 0.42573(8) 0.52735(7) 0.0887(3) Uani 1 1 d . . .
C3 C 0.17008(11) 0.3830(2) 0.43310(19) 0.0583(6) Uani 1 1 d . . .
N5 N 0.16554(11) 0.2958(2) 0.39078(16) 0.0719(7) Uani 1 1 d . . .
H5B H 0.1296 0.2766 0.3429 0.086 Uiso 1 1 calc R . .
H5C H 0.1985 0.2578 0.4110 0.086 Uiso 1 1 calc R . .
N6 N 0.11785(11) 0.4370(2) 0.3986(2) 0.0796(8) Uani 1 1 d . . .
H6C H 0.0829 0.4148 0.3506 0.095 Uiso 1 1 calc R . .
H6D H 0.1186 0.4947 0.4241 0.095 Uiso 1 1 calc R . .
S4 S 0.0000 -0.39217(7) 0.2500 0.0600(3) Uani 1 2 d S . .
C4 C 0.0000 -0.2620(3) 0.2500 0.0528(8) Uani 1 2 d S . .
N7 N 0.02216(13) -0.20902(18) 0.32735(18) 0.0773(7) Uani 1 1 d . . .
H7D H 0.0218 -0.1424 0.3261 0.093 Uiso 1 1 calc R . .
H7E H 0.0370 -0.2411 0.3790 0.093 Uiso 1 1 calc R . .
O1 O 0.04639(7) 0.18617(12) 0.25784(10) 0.0460(4) Uani 1 1 d . . .
O2 O 0.0000 0.33600(17) 0.2500 0.0477(5) Uani 1 2 d S . .
C5 C 0.0000 0.2364(2) 0.2500 0.0395(6) Uani 1 2 d S . .
N8 N 0.31181(11) 0.19643(19) 0.24088(19) 0.0698(6) Uani 1 1 d . . .
C6 C 0.3254(2) 0.0847(3) 0.2333(3) 0.0995(12) Uani 1 1 d . . .
H6A H 0.3708 0.0735 0.2742 0.119 Uiso 1 1 calc R . .
H6B H 0.3132 0.0719 0.1702 0.119 Uiso 1 1 calc R . .
C7 C 0.2922(2) 0.0054(3) 0.2572(3) 0.1128(15) Uani 1 1 d . . .
H7A H 0.3036 -0.0632 0.2504 0.169 Uiso 1 1 calc R . .
H7B H 0.2472 0.0141 0.2160 0.169 Uiso 1 1 calc R . .
H7C H 0.3049 0.0156 0.3202 0.169 Uiso 1 1 calc R . .
C8 C 0.3255(2) 0.2240(3) 0.3335(3) 0.0946(11) Uani 1 1 d . . .
H8A H 0.2973 0.1843 0.3432 0.114 Uiso 1 1 calc R . .
H8B H 0.3155 0.2967 0.3326 0.114 Uiso 1 1 calc R . .
C9 C 0.3928(2) 0.2059(4) 0.4157(3) 0.1320(18) Uani 1 1 d . . .
H9A H 0.3966 0.2258 0.4719 0.198 Uiso 1 1 calc R . .
H9B H 0.4213 0.2466 0.4085 0.198 Uiso 1 1 calc R . .
H9C H 0.4032 0.1338 0.4188 0.198 Uiso 1 1 calc R . .
C10 C 0.35149(17) 0.2587(3) 0.2166(3) 0.0933(11) Uani 1 1 d . . .
H10A H 0.3957 0.2420 0.2615 0.112 Uiso 1 1 calc R . .
H10B H 0.3409 0.2360 0.1562 0.112 Uiso 1 1 calc R . .
C11 C 0.3443(2) 0.3739(3) 0.2140(3) 0.1068(13) Uani 1 1 d . . .
H11A H 0.3705 0.4052 0.1967 0.160 Uiso 1 1 calc R . .
H11B H 0.3570 0.3985 0.2743 0.160 Uiso 1 1 calc R . .
H11C H 0.3008 0.3921 0.1693 0.160 Uiso 1 1 calc R . .
C12 C 0.24159(15) 0.2196(3) 0.1694(3) 0.0878(10) Uani 1 1 d . . .
H12A H 0.2170 0.1738 0.1820 0.105 Uiso 1 1 calc R . .
H12B H 0.2334 0.2900 0.1796 0.105 Uiso 1 1 calc R . .
C13 C 0.2171(2) 0.2089(5) 0.0683(3) 0.1269(17) Uani 1 1 d . . .
H13A H 0.1728 0.2256 0.0307 0.190 Uiso 1 1 calc R . .
H13B H 0.2232 0.1389 0.0559 0.190 Uiso 1 1 calc R . .
H13C H 0.2398 0.2554 0.0536 0.190 Uiso 1 1 calc R . .
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
N2 C1 N1 116.6(2) . . ?
N2 C1 S1 121.79(19) . . ?
N1 C1 S1 121.59(18) . . ?
N3 C2 N4 117.7(2) . . ?
N3 C2 S2 121.57(19) . . ?
N4 C2 S2 120.75(19) . . ?
N6 C3 N5 116.8(2) . . ?
N6 C3 S3 121.0(2) . . ?
N5 C3 S3 122.3(2) . . ?
N7 C4 N7 117.6(3) . 2 ?
N7 C4 S4 121.21(17) . . ?
N7 C4 S4 121.21(17) 2 . ?
O2 C5 O1 120.26(14) . 2 ?
O2 C5 O1 120.26(14) . . ?
O1 C5 O1 119.5(3) 2 . ?
C8 N8 C6 113.4(3) . . ?
C8 N8 C10 112.5(3) . . ?
C6 N8 C10 105.1(3) . . ?
C8 N8 C12 106.9(3) . . ?
C6 N8 C12 109.8(3) . . ?
C10 N8 C12 109.1(3) . . ?
N8 C6 C7 115.3(3) . . ?
N8 C8 C9 116.1(4) . . ?
C11 C10 N8 116.4(3) . . ?
C13 C12 N8 117.4(3) . . ?
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
S1 C1 1.698(2) . ?
C1 N2 1.315(3) . ?
C1 N1 1.326(3) . ?
S2 C2 1.701(2) . ?
C2 N3 1.319(3) . ?
C2 N4 1.323(3) . ?
S3 C3 1.699(3) . ?
C3 N6 1.312(3) . ?
C3 N5 1.313(4) . ?
S4 C4 1.679(4) . ?
C4 N7 1.319(3) . ?
C4 N7 1.319(3) 2 ?
O1 C5 1.286(2) . ?
O2 C5 1.285(4) . ?
C5 O1 1.286(2) 2 ?
N8 C8 1.485(4) . ?
N8 C6 1.506(4) . ?
N8 C10 1.523(4) . ?
N8 C12 1.531(4) . ?
C6 C7 1.525(6) . ?
C8 C9 1.513(6) . ?
C10 C11 1.495(5) . ?
C12 C13 1.506(6) . ?
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 H1A O1 0.86 2.15 2.913(3) 147.4 2
N4 H4B O1 0.86 2.05 2.892(3) 165.5 2
N2 H2A O1 0.86 2.05 2.874(3) 160.1 .
N2 H2B S3 0.86 2.74 3.480(2) 144.5 7_556
N5 H5C S3 0.86 2.71 3.486(3) 151.2 7_556
N3 H3A O2 0.86 2.13 2.958(2) 161.4 .
N3 H3B S2 0.86 2.64 3.433(2) 154.1 5_566
N6 H6D S2 0.86 2.89 3.636(3) 146.1 5_566
N5 H5B O1 0.86 2.13 2.949(3) 159.6 .
N4 H4C S1 0.86 2.68 3.469(2) 153.5 5_556
N7 H7E S2 0.86 2.58 3.405(3) 162.3 5_556
N1 H1B S1 0.86 2.67 3.477(2) 157.9 5_556
N6 H6C O2 0.86 2.10 2.949(3) 168.8 .
N7 H7D N1 0.86 2.60 3.367(3) 149.0 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N8 C6 C7 55.1(5) . . . . ?
C10 N8 C6 C7 178.4(4) . . . . ?
C12 N8 C6 C7 -64.4(4) . . . . ?
C6 N8 C8 C9 58.1(4) . . . . ?
C10 N8 C8 C9 -60.9(4) . . . . ?
C12 N8 C8 C9 179.3(3) . . . . ?
C8 N8 C10 C11 -59.2(4) . . . . ?
C6 N8 C10 C11 177.0(4) . . . . ?
C12 N8 C10 C11 59.3(4) . . . . ?
C8 N8 C12 C13 173.6(4) . . . . ?
C6 N8 C12 C13 -62.9(5) . . . . ?
C10 N8 C12 C13 51.7(5) . . . . ?
