#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/51/4505154.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_4505154
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            'C15 H25 N4 O9 S'
_chemical_formula_weight         437.45
_space_group_IT_number           34
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 -2n'
_symmetry_space_group_name_H-M   'P n n 2'
_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                   13.5047(10)
_cell_length_b                   22.3136(17)
_cell_length_c                   6.8889(5)
_cell_measurement_temperature    173(2)
_cell_volume                     2075.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14870
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.03, Sheldrick, (1999)'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2641
_reflns_number_total             3640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050118xsi20050330_041133.cif
_cod_data_source_block           e:\x-ray\1a
_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      Pnn2
_cod_database_code               4505154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'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
S1 S 0.60404(5) 0.27025(3) 0.35690(14) 0.02919(19) Uani 1 1 d .
O1 O 0.65657(18) 0.26303(11) 0.5401(3) 0.0348(6) Uani 1 1 d .
N1 N 0.4267(2) 0.43861(14) -0.0060(4) 0.0404(8) Uani 1 1 d .
C1 C 0.5720(2) 0.34715(13) 0.3392(5) 0.0277(7) Uani 1 1 d .
O2 O 0.66498(18) 0.25762(11) 0.1882(3) 0.0349(6) Uani 1 1 d .
N2 N 0.52312(18) 0.23160(12) -0.1412(6) 0.0410(7) Uani 1 1 d .
H2A H 0.5572 0.2351 -0.2494 0.049 Uiso 1 1 calc R
H2B H 0.5540 0.2250 -0.0307 0.049 Uiso 1 1 calc R
C2 C 0.5146(2) 0.36488(14) 0.1834(5) 0.0287(8) Uani 1 1 d .
H2 H 0.4940 0.3363 0.0894 0.034 Uiso 1 1 calc R
O3 O 0.50994(14) 0.23769(9) 0.3538(4) 0.0349(5) Uani 1 1 d .
N3 N 0.3801(2) 0.24620(14) -0.3106(4) 0.0360(8) Uani 1 1 d .
H3A H 0.3153 0.2503 -0.3144 0.043 Uiso 1 1 calc R
H3B H 0.4150 0.2488 -0.4182 0.043 Uiso 1 1 calc R
C3 C 0.4873(2) 0.42409(15) 0.1649(5) 0.0282(8) Uani 1 1 d .
O4 O 0.4175(3) 0.40061(14) -0.1299(5) 0.0903(12) Uani 1 1 d .
N4 N 0.3738(2) 0.23233(14) 0.0176(4) 0.0404(8) Uani 1 1 d .
H4A H 0.3089 0.2363 0.0155 0.049 Uiso 1 1 calc R
H4B H 0.4045 0.2257 0.1281 0.049 Uiso 1 1 calc R
C4 C 0.5149(2) 0.46740(15) 0.2996(4) 0.0287(8) Uani 1 1 d .
O5 O 0.38839(18) 0.48745(12) -0.0203(4) 0.0507(7) Uani 1 1 d .
C5 C 0.5736(3) 0.44837(15) 0.4533(6) 0.0364(9) Uani 1 1 d .
H5 H 0.5952 0.4769 0.5465 0.044 Uiso 1 1 calc R
O6 O 0.8951(2) 0.45135(13) 0.0531(5) 0.0653(9) Uani 1 1 d .
C6 C 0.6019(2) 0.38843(15) 0.4752(5) 0.0357(8) Uani 1 1 d .
H6 H 0.6413 0.3764 0.5826 0.043 Uiso 1 1 calc R
O7 O 0.81636(19) 0.36574(12) -0.2023(4) 0.0542(8) Uani 1 1 d .
C7 C 0.4247(2) 0.23631(13) -0.1446(6) 0.0299(7) Uani 1 1 d .
O8 O 0.11577(18) 0.39526(15) 0.5371(4) 0.0603(8) Uani 1 1 d .
C8 C 0.9548(3) 0.4205(2) -0.0810(8) 0.0686(15) Uani 1 1 d .
H8A H 0.9818 0.3838 -0.0196 0.082 Uiso 1 1 calc R
H8B H 1.0112 0.4462 -0.1201 0.082 Uiso 1 1 calc R
O9 O 0.27931(18) 0.41416(14) 0.2949(4) 0.0567(8) Uani 1 1 d .
C9 C 0.8956(3) 0.4037(2) -0.2566(6) 0.0628(13) Uani 1 1 d .
H9A H 0.8693 0.4403 -0.3192 0.075 Uiso 1 1 calc R
H9B H 0.9387 0.3828 -0.3514 0.075 Uiso 1 1 calc R
C10 C 0.7566(3) 0.3949(2) -0.0629(7) 0.0568(12) Uani 1 1 d .
H10A H 0.7039 0.3671 -0.0196 0.068 Uiso 1 1 calc R
H10B H 0.7244 0.4300 -0.1236 0.068 Uiso 1 1 calc R
C11 C 0.8143(4) 0.41476(19) 0.1073(7) 0.0593(12) Uani 1 1 d .
H11A H 0.7705 0.4374 0.1962 0.071 Uiso 1 1 calc R
H11B H 0.8393 0.3792 0.1781 0.071 Uiso 1 1 calc R
C12 C 0.1816(3) 0.41389(19) 0.2181(6) 0.0469(10) Uani 1 1 d .
H12A H 0.1644 0.3730 0.1737 0.056 Uiso 1 1 calc R
H12B H 0.1780 0.4412 0.1050 0.056 Uiso 1 1 calc R
C13 C 0.1104(3) 0.43356(19) 0.3688(7) 0.0601(11) Uani 1 1 d .
H13A H 0.1253 0.4754 0.4071 0.072 Uiso 1 1 calc R
H13B H 0.0424 0.4325 0.3151 0.072 Uiso 1 1 calc R
C14 C 0.2134(3) 0.39513(19) 0.6122(6) 0.0496(11) Uani 1 1 d .
H14A H 0.2173 0.3674 0.7242 0.060 Uiso 1 1 calc R
H14B H 0.2308 0.4358 0.6583 0.060 Uiso 1 1 calc R
C15 C 0.2849(3) 0.3760(2) 0.4600(6) 0.0536(11) Uani 1 1 d .
H15A H 0.3529 0.3770 0.5135 0.064 Uiso 1 1 calc R
H15B H 0.2702 0.3343 0.4206 0.064 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_3
O2 S1 O1 113.34(12) .
O2 S1 O3 112.59(16) .
O1 S1 O3 112.36(15) .
O2 S1 C1 105.72(15) .
O1 S1 C1 106.58(15) .
O3 S1 C1 105.49(12) .
O4 N1 O5 122.0(3) .
O4 N1 C3 117.9(3) .
O5 N1 C3 120.1(3) .
C6 C1 C2 120.2(3) .
C6 C1 S1 122.0(3) .
C2 C1 S1 117.9(3) .
C3 C2 C1 119.8(3) .
C2 C3 C4 122.2(3) .
C2 C3 N1 115.8(3) .
C4 C3 N1 122.0(3) .
C5 C4 C3 116.7(3) .
C5 C4 C4 116.6(3) 2_665
C3 C4 C4 126.7(2) 2_665
C4 C5 C6 122.0(3) .
C8 O6 C11 109.5(3) .
C1 C6 C5 119.1(3) .
C10 O7 C9 109.7(3) .
N3 C7 N4 120.8(3) .
N3 C7 N2 119.1(4) .
N4 C7 N2 120.1(4) .
C14 O8 C13 110.0(3) .
O6 C8 C9 110.3(3) .
C12 O9 C15 110.1(3) .
O7 C9 C8 109.9(4) .
O7 C10 C11 112.2(3) .
O6 C11 C10 111.8(4) .
O9 C12 C13 109.9(3) .
O8 C13 C12 110.8(3) .
O8 C14 C15 110.3(3) .
O9 C15 C14 111.0(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.452(3) .
S1 O1 1.457(3) .
S1 O3 1.464(2) .
S1 C1 1.774(3) .
N1 O4 1.209(4) .
N1 O5 1.211(3) .
N1 C3 1.470(4) .
C1 C6 1.375(4) .
C1 C2 1.382(4) .
N2 C7 1.334(4) .
C2 C3 1.377(4) .
N3 C7 1.311(5) .
C3 C4 1.391(4) .
N4 C7 1.315(5) .
C4 C5 1.389(5) .
C4 C4 1.510(7) 2_665
C5 C6 1.399(5) .
O6 C8 1.407(5) .
O6 C11 1.413(5) .
O7 C10 1.412(4) .
O7 C9 1.415(5) .
O8 C14 1.417(4) .
O8 C13 1.443(5) .
C8 C9 1.497(6) .
O9 C12 1.421(4) .
O9 C15 1.422(4) .
C10 C11 1.477(6) .
C12 C13 1.482(6) .
C14 C15 1.487(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145743
