#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/51/4505156.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_4505156
loop_
_publ_author_name
'Custelcean, Radu'
'Ward, Michael D.'
_publ_section_title
;
 Chiral Discrimination in Low-Density Hydrogen-Bonded Frameworks
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2277
_journal_paper_doi               10.1021/cg050118x
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C14 H18 N8 O10 S2'
_chemical_formula_weight         522.48
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9757(10)
_cell_length_b                   7.2578(5)
_cell_length_c                   20.0261(13)
_cell_measurement_temperature    173(2)
_cell_volume                     2176.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10496
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.43(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                3164
_reflns_number_total             3808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050118xsi20050330_041210.cif
_cod_data_source_block           e:\xray\no2\pca21
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorombic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               4505156
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
S1 S 0.34466(5) 0.11472(11) 0.13883(4) 0.02216(18) Uani 1 1 d .
S2 S 0.92240(5) -0.07699(12) -0.16267(4) 0.0258(2) Uani 1 1 d .
O1 O 0.62047(13) 0.3833(3) -0.07609(10) 0.0276(5) Uani 1 1 d .
O2 O 0.29545(14) -0.0528(3) 0.12591(10) 0.0274(5) Uani 1 1 d .
O3 O 0.37702(15) 0.1237(3) 0.20763(10) 0.0288(5) Uani 1 1 d .
O4 O 0.98560(14) 0.0730(3) -0.15398(11) 0.0328(6) Uani 1 1 d .
O5 O 0.70996(14) 0.3638(3) 0.05561(10) 0.0276(5) Uani 1 1 d .
N6 N 0.91850(19) 0.4146(4) -0.21657(15) 0.0381(8) Uani 1 1 d .
H6A H 0.9335 0.3129 -0.1977 0.046 Uiso 1 1 calc R
H6B H 0.9278 0.5177 -0.1966 0.046 Uiso 1 1 calc R
O7 O 0.88524(14) -0.0851(3) -0.23018(10) 0.0293(6) Uani 1 1 d .
N8 N 0.35291(18) -0.3882(4) 0.18761(13) 0.0302(7) Uani 1 1 d .
H8A H 0.3477 -0.2877 0.1652 0.036 Uiso 1 1 calc R
H8B H 0.3534 -0.4925 0.1673 0.036 Uiso 1 1 calc R
O9 O 0.29827(14) 0.2803(3) 0.11811(10) 0.0278(5) Uani 1 1 d .
C10 C 0.3602(2) -0.3822(5) 0.25344(16) 0.0258(8) Uani 1 1 d .
N11 N 0.56088(17) 0.3961(4) -0.03386(13) 0.0265(6) Uani 1 1 d .
O12 O 0.85158(16) 0.3599(3) 0.03493(12) 0.0423(7) Uani 1 1 d .
C13 C 0.8363(2) 0.1158(4) -0.06365(14) 0.0226(7) Uani 1 1 d .
H13 H 0.8890 0.1825 -0.0591 0.027 Uiso 1 1 calc R
N14 N 0.85931(18) 0.5718(4) -0.30495(14) 0.0369(7) Uani 1 1 d .
H14A H 0.8355 0.5734 -0.3440 0.044 Uiso 1 1 calc R
H14B H 0.8691 0.6734 -0.2841 0.044 Uiso 1 1 calc R
N15 N 0.86698(17) 0.2550(4) -0.30683(14) 0.0347(7) Uani 1 1 d .
H15A H 0.8432 0.2527 -0.3459 0.042 Uiso 1 1 calc R
H15B H 0.8816 0.1536 -0.2874 0.042 Uiso 1 1 calc R
N16 N 0.35947(16) -0.2222(4) 0.28475(12) 0.0292(7) Uani 1 1 d .
H16A H 0.3543 -0.1217 0.2624 0.035 Uiso 1 1 calc R
H16B H 0.3642 -0.2186 0.3275 0.035 Uiso 1 1 calc R
O17 O 0.95511(14) -0.2545(3) -0.14019(10) 0.0329(6) Uani 1 1 d .
N18 N 0.36605(17) -0.5381(4) 0.28776(12) 0.0298(7) Uani 1 1 d .
H18A H 0.3694 -0.5352 0.3306 0.036 Uiso 1 1 calc R
H18B H 0.3665 -0.6420 0.2671 0.036 Uiso 1 1 calc R
C19 C 0.8809(2) 0.4126(5) -0.27681(16) 0.0273(8) Uani 1 1 d .
C20 C 0.68258(19) 0.0588(4) -0.02915(15) 0.0218(7) Uani 1 1 d .
C21 C 0.44302(19) 0.1033(4) 0.08874(15) 0.0210(7) Uani 1 1 d .
C22 C 0.5999(2) 0.0878(5) 0.01250(15) 0.0226(7) Uani 1 1 d .
C23 C 0.5773(2) -0.0545(4) 0.05612(16) 0.0249(8) Uani 1 1 d .
H23 H 0.6148 -0.1561 0.0597 0.030 Uiso 1 1 calc R
O24 O 0.51956(18) 0.5367(3) -0.02492(14) 0.0517(7) Uani 1 1 d .
C25 C 0.5001(2) -0.0476(4) 0.09422(16) 0.0252(7) Uani 1 1 d .
H25 H 0.4864 -0.1433 0.1233 0.030 Uiso 1 1 calc R
C26 C 0.7529(2) -0.1267(4) -0.11478(17) 0.0303(7) Uani 1 1 d .
H26 H 0.7497 -0.2244 -0.1447 0.036 Uiso 1 1 calc R
C27 C 0.76325(19) 0.1555(4) -0.02390(14) 0.0190(6) Uani 1 1 d .
C28 C 0.6802(2) -0.0845(5) -0.07490(17) 0.0301(8) Uani 1 1 d .
H28 H 0.6283 -0.1542 -0.0789 0.036 Uiso 1 1 calc R
C29 C 0.82996(19) -0.0237(5) -0.11003(15) 0.0229(7) Uani 1 1 d .
N30 N 0.77523(17) 0.3044(4) 0.02499(13) 0.0259(6) Uani 1 1 d .
C31 C 0.5414(2) 0.2367(4) 0.00837(14) 0.0217(7) Uani 1 1 d .
C32 C 0.4632(2) 0.2452(4) 0.04595(14) 0.0217(7) Uani 1 1 d .
H32 H 0.4251 0.3458 0.0421 0.026 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
O2 S1 O9 113.71(13)
O2 S1 O3 112.04(13)
O9 S1 O3 113.07(13)
O2 S1 C21 106.34(13)
O9 S1 C21 105.87(13)
O3 S1 C21 104.97(13)
O17 S2 O4 114.11(13)
O17 S2 O7 112.31(14)
O4 S2 O7 112.87(14)
O17 S2 C29 105.75(14)
O4 S2 C29 105.82(14)
O7 S2 C29 105.06(13)
N16 C10 N8 120.1(3)
N16 C10 N18 120.3(3)
N8 C10 N18 119.6(3)
O24 N11 O1 122.4(3)
O24 N11 C31 118.8(3)
O1 N11 C31 118.8(3)
C29 C13 C27 119.1(3)
N15 C19 N14 121.9(3)
N15 C19 N6 119.5(3)
N14 C19 N6 118.6(3)
C28 C20 C27 116.6(3)
C28 C20 C22 116.7(3)
C27 C20 C22 126.6(3)
C32 C21 C25 120.2(3)
C32 C21 S1 119.9(2)
C25 C21 S1 119.9(2)
C23 C22 C31 117.3(3)
C23 C22 C20 116.3(3)
C31 C22 C20 126.3(3)
C25 C23 C22 121.4(3)
C23 C25 C21 119.8(3)
C29 C26 C28 119.9(3)
C13 C27 C20 122.3(3)
C13 C27 N30 116.1(3)
C20 C27 N30 121.6(3)
C26 C28 C20 121.8(3)
C13 C29 C26 120.2(3)
C13 C29 S2 120.3(2)
C26 C29 S2 119.5(2)
O12 N30 O5 122.9(3)
O12 N30 C27 117.6(3)
O5 N30 C27 119.5(2)
C32 C31 C22 122.0(3)
C32 C31 N11 116.4(3)
C22 C31 N11 121.5(3)
C21 C32 C31 119.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.445(2)
S1 O9 1.449(2)
S1 O3 1.462(2)
S1 C21 1.784(3)
S2 O17 1.450(2)
S2 O4 1.453(2)
S2 O7 1.463(2)
S2 C29 1.783(3)
O1 N11 1.233(3)
O5 N30 1.232(3)
N6 C19 1.332(4)
N8 C10 1.323(4)
C10 N16 1.319(4)
C10 N18 1.327(4)
N11 O24 1.207(3)
N11 C31 1.462(4)
O12 N30 1.228(3)
C13 C29 1.377(4)
C13 C27 1.383(4)
N14 C19 1.325(4)
N15 C19 1.309(4)
C20 C28 1.387(5)
C20 C27 1.401(4)
C20 C22 1.508(4)
C21 C32 1.373(4)
C21 C25 1.394(4)
C22 C23 1.394(4)
C22 C31 1.394(4)
C23 C25 1.386(4)
C26 C29 1.379(4)
C26 C28 1.384(5)
C27 N30 1.469(4)
C31 C32 1.393(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145744
