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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520437.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.
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data_1520437
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C10H20N4O6S2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              628
_journal_year                    2009
_chemical_formula_sum            'C10 H20 N4 O6 S2'
_chemical_formula_weight         356.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.664(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2331(6)
_cell_length_b                   11.7105(6)
_cell_length_c                   10.2193(5)
_cell_measurement_reflns_used    18603
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1561.17(13)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15777
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0893
_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)+(0.0000P)²+6.5721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                2282
_reflns_number_total             3546
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-628.cif
_cod_data_source_block           2008src1284p21c
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/628)

More at:
http://ecrystals.chem.soton.ac.uk/628/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C2 C -0.2535(4) 0.6226(4) 0.2815(5) 0.0245(11) Uani 1 1 d . . .
H2 H -0.2768 0.6993 0.2818 0.029 Uiso 1 1 calc R . .
C3 C -0.1883(4) 0.5837(4) 0.3935(5) 0.0263(12) Uani 1 1 d . . .
H3 H -0.1704 0.6299 0.4703 0.032 Uiso 1 1 calc R . .
C4 C -0.1518(4) 0.4763(4) 0.3871(5) 0.0236(11) Uani 1 1 d . . .
H4 H -0.1039 0.4468 0.4589 0.028 Uiso 1 1 calc R . .
C6 C -0.2519(3) 0.4519(4) 0.1752(5) 0.0173(10) Uani 1 1 d . . .
C8 C -0.2587(4) 0.2640(4) 0.0599(5) 0.0256(12) Uani 1 1 d . . .
H8A H -0.2181 0.2379 0.1448 0.031 Uiso 1 1 calc R . .
H8B H -0.2159 0.2554 -0.0102 0.031 Uiso 1 1 calc R . .
C9 C -0.3543(4) 0.1911(4) 0.0260(5) 0.0205(11) Uani 1 1 d . . .
H9A H -0.3350 0.1109 0.0118 0.025 Uiso 1 1 calc R . .
H9B H -0.3938 0.1928 0.1002 0.025 Uiso 1 1 calc R . .
C11 C -0.4488(4) 0.3562(4) -0.0792(5) 0.0200(10) Uani 1 1 d . . .
H11A H -0.4891 0.3615 -0.0061 0.024 Uiso 1 1 calc R . .
H11B H -0.4920 0.3837 -0.1617 0.024 Uiso 1 1 calc R . .
C12 C -0.3531(4) 0.4287(4) -0.0477(5) 0.0212(11) Uani 1 1 d . . .
H12A H -0.3159 0.4277 -0.1239 0.025 Uiso 1 1 calc R . .
H12B H -0.3724 0.5087 -0.0323 0.025 Uiso 1 1 calc R . .
C13 C -0.6035(4) 0.1447(4) -0.0680(5) 0.0233(11) Uani 1 1 d . . .
H13A H -0.6593 0.0948 -0.1092 0.028 Uiso 1 1 calc R . .
H13B H -0.6305 0.2214 -0.0569 0.028 Uiso 1 1 calc R . .
H13C H -0.5733 0.1139 0.0190 0.028 Uiso 1 1 calc R . .
N1 N -0.2853(3) 0.5604(4) 0.1744(4) 0.0219(9) Uani 1 1 d . . .
N5 N -0.1832(3) 0.4103(3) 0.2783(4) 0.0192(9) Uani 1 1 d . . .
H55 H -0.1591 0.3406 0.2746 0.023 Uiso 1 1 calc R . .
N7 N -0.2862(3) 0.3848(3) 0.0712(4) 0.0208(9) Uani 1 1 d . . .
N10 N -0.4177(3) 0.2364(3) -0.0959(4) 0.0190(9) Uani 1 1 d . . .
O1 O -0.4638(3) 0.0409(3) -0.1753(3) 0.0267(8) Uani 1 1 d . . .
O2 O -0.5528(3) 0.2064(3) -0.2924(3) 0.0242(8) Uani 1 1 d . . .
S1 S -0.50914(10) 0.15199(10) -0.16976(12) 0.0196(3) Uani 1 1 d . . .
C21 C 0.1225(4) 0.4151(5) 0.0644(5) 0.0324(13) Uani 1 1 d . . .
H21A H 0.0674 0.3607 0.0333 0.039 Uiso 1 1 calc R . .
H21B H 0.1886 0.3814 0.0541 0.039 Uiso 1 1 calc R . .
H21C H 0.1114 0.4854 0.0119 0.039 Uiso 1 1 calc R . .
O21 O 0.1314(3) 0.3364(3) 0.3002(3) 0.0261(8) Uani 1 1 d . . .
O22 O 0.0256(3) 0.5036(3) 0.2391(4) 0.0318(9) Uani 1 1 d . . .
O23 O 0.2103(3) 0.5203(3) 0.2765(3) 0.0265(8) Uani 1 1 d . . .
S2 S 0.12284(9) 0.44675(11) 0.23299(12) 0.0211(3) Uani 1 1 d . . .
O1W O 0.0532(3) 0.7358(3) 0.1853(4) 0.0326(9) Uani 1 1 d D . .
H1W H -0.006(2) 0.764(4) 0.185(6) 0.040(18) Uiso 1 1 d D . .
H2W H 0.051(4) 0.669(3) 0.216(7) 0.06(2) Uiso 1 1 d D . .
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
N1 C2 C3 124.6(5) . .
N1 C2 H2 117.7 . .
C3 C2 H2 117.7 . .
C4 C3 C2 116.2(5) . .
C4 C3 H3 121.9 . .
C2 C3 H3 121.9 . .
C3 C4 N5 120.3(5) . .
C3 C4 H4 119.8 . .
N5 C4 H4 119.9 . .
N7 C6 N1 118.8(4) . .
N7 C6 N5 119.9(4) . .
N1 C6 N5 121.3(4) . .
N7 C8 C9 110.6(4) . .
N7 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
N7 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N10 C9 C8 108.8(4) . .
N10 C9 H9A 109.9 . .
C8 C9 H9A 109.9 . .
N10 C9 H9B 109.9 . .
C8 C9 H9B 109.9 . .
H9A C9 H9B 108.3 . .
N10 C11 C12 108.5(4) . .
N10 C11 H11A 110.0 . .
C12 C11 H11A 110.0 . .
N10 C11 H11B 110.0 . .
C12 C11 H11B 110.0 . .
H11A C11 H11B 108.4 . .
N7 C12 C11 110.3(4) . .
N7 C12 H12A 109.6 . .
C11 C12 H12A 109.6 . .
N7 C12 H12B 109.6 . .
C11 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
S1 C13 H13A 109.5 . .
S1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
S1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C2 N1 C6 117.1(4) . .
C6 N5 C4 120.2(4) . .
C6 N5 H55 119.9 . .
C4 N5 H55 119.9 . .
C6 N7 C8 124.9(4) . .
C6 N7 C12 121.8(4) . .
C8 N7 C12 113.2(4) . .
C9 N10 C11 111.9(4) . .
C9 N10 S1 116.1(3) . .
C11 N10 S1 115.2(3) . .
O1 S1 O2 118.4(2) . .
O1 S1 N10 106.4(2) . .
O2 S1 N10 106.9(2) . .
O1 S1 C13 108.8(2) . .
O2 S1 C13 108.5(2) . .
N10 S1 C13 107.4(2) . .
S2 C21 H21A 109.5 . .
S2 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
S2 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O23 S2 O21 112.7(2) . .
O23 S2 O22 112.3(2) . .
O21 S2 O22 112.5(2) . .
O23 S2 C21 107.2(2) . .
O21 S2 C21 105.2(2) . .
O22 S2 C21 106.3(3) . .
H1W O1W H2W 105(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.323(6) .
C2 C3 1.390(7) .
C2 H2 0.9500 .
C3 C4 1.353(7) .
C3 H3 0.9500 .
C4 N5 1.361(6) .
C4 H4 0.9500 .
C6 N7 1.338(6) .
C6 N1 1.345(6) .
C6 N5 1.361(6) .
C8 N7 1.470(6) .
C8 C9 1.518(7) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N10 1.478(6) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C11 N10 1.480(6) .
C11 C12 1.513(7) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N7 1.470(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 S1 1.756(5) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N5 H55 0.8800 .
N10 S1 1.645(4) .
O1 S1 1.438(4) .
O2 S1 1.438(3) .
C21 S2 1.762(5) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
O21 S2 1.459(4) .
O22 S2 1.459(4) .
O23 S2 1.452(4) .
O1W H1W 0.849(19) .
O1W H2W 0.841(19) .
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
O1W H2W O22 0.841(19) 1.99(3) 2.811(5) 165(7) .
O1W H2W S2 0.841(19) 2.77(3) 3.521(4) 149(5) .
N5 H55 O1W 0.88 1.86 2.658(5) 150.4 2_545
O1W H1W O21 0.849(19) 1.89(2) 2.738(5) 174(6) 2
O1W H1W S2 0.849(19) 2.85(3) 3.588(4) 147(5) 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045556
