#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/95/2229520.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229520
loop_
_publ_author_name
'Wang, Ning-Yu'
'Deng, Mei'
'Xia, Yong'
'Yu, Luo-Ting'
_publ_section_title
;
 6-Chloro-9-(2-nitrophenylsulfonyl)-9H-purine
;
_journal_coeditor_code           SU2246
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o687
_journal_paper_doi               10.1107/S1600536811003102
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C11 H6 Cl N5 O4 S'
_chemical_formula_sum            'C11 H6 Cl N5 O4 S'
_chemical_formula_weight         339.72
_chemical_name_systematic
;
6-Chloro-9-(2-nitrophenylsulfonyl)-9H-purine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.692(3)
_cell_angle_beta                 97.136(3)
_cell_angle_gamma                93.995(3)
_cell_formula_units_Z            4
_cell_length_a                   10.0055(3)
_cell_length_b                   10.6931(5)
_cell_length_c                   12.5378(5)
_cell_measurement_reflns_used    5646
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1341
_cell_measurement_theta_min      3.0875
_cell_volume                     1324.17(9)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10984
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.99195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0366
_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)+(0.0398P)²+0.4744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                4389
_reflns_number_total             5403
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2246.cif
_cod_data_source_block           I
_cod_original_cell_volume        1324.16(9)
_cod_database_code               2229520
_cod_database_fobs_code          2229520
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.28373(6) 1.01998(7) 0.86805(5) 0.05386(18) Uani d . 1 . .
Cl Cl2 -0.10359(6) 0.30928(6) 0.45966(6) 0.05239(17) Uani d . 1 . .
S S1 0.31769(5) 1.10135(5) 0.71476(4) 0.02990(13) Uani d . 1 . .
S S2 0.29292(5) 0.60128(5) 0.16093(4) 0.03061(13) Uani d . 1 . .
O O1 0.33387(14) 1.21495(14) 0.66297(12) 0.0373(3) Uani d . 1 . .
O O2 0.39441(14) 1.08250(15) 0.81453(11) 0.0403(4) Uani d . 1 . .
O O3 0.11604(15) 1.08355(17) 0.49868(14) 0.0495(4) Uani d . 1 . .
O O4 0.25354(19) 1.11017(18) 0.38100(14) 0.0578(5) Uani d . 1 . .
O O5 0.22219(15) 0.63512(15) 0.06322(11) 0.0405(4) Uani d . 1 . .
O O6 0.37133(15) 0.69221(15) 0.23407(12) 0.0446(4) Uani d . 1 . .
O O7 0.13521(15) 0.38259(17) 0.02911(13) 0.0468(4) Uani d . 1 . .
O O8 0.2366(2) 0.3163(2) -0.10209(14) 0.0737(6) Uani d . 1 . .
N N2 -0.0813(2) 0.8795(2) 0.90380(17) 0.0505(5) Uani d . 1 . .
N N4 0.13616(18) 0.90598(18) 0.84106(15) 0.0419(5) Uani d . 1 . .
N N7 -0.05280(17) 1.15618(18) 0.74289(14) 0.0375(4) Uani d . 1 . .
N N9 0.15488(16) 1.08978(16) 0.73571(13) 0.0308(4) Uani d . 1 . .
N N16 0.21920(18) 1.06359(17) 0.46067(14) 0.0369(4) Uani d . 1 . .
N N18 0.15591(18) 0.36990(18) 0.50525(15) 0.0402(4) Uani d . 1 . .
N N20 0.30089(16) 0.47424(17) 0.39320(13) 0.0335(4) Uani d . 1 . .
N N23 -0.03515(17) 0.4610(2) 0.25421(15) 0.0409(5) Uani d . 1 . .
N N25 0.17329(15) 0.53615(17) 0.22797(13) 0.0303(4) Uani d . 1 . .
N N32 0.23641(18) 0.35675(18) -0.00913(14) 0.0387(4) Uani d . 1 . .
C C1 -0.1216(2) 0.9794(2) 0.85674(18) 0.0391(5) Uani d . 1 . .
C C3 0.0440(2) 0.8481(2) 0.8933(2) 0.0517(6) Uani d . 1 . .
H H3 0.0702 0.7769 0.9267 0.062 Uiso calc R 1 . .
C C5 0.0901(2) 1.0062(2) 0.79701(16) 0.0315(4) Uani d . 1 . .
C C6 -0.0380(2) 1.0496(2) 0.79999(16) 0.0331(5) Uani d . 1 . .
C C8 0.0617(2) 1.1767(2) 0.70684(17) 0.0358(5) Uani d . 1 . .
H H8 0.0802 1.2434 0.6654 0.043 Uiso calc R 1 . .
C C10 0.33847(18) 0.97337(19) 0.62325(15) 0.0287(4) Uani d . 1 . .
C C11 0.30456(19) 0.9715(2) 0.51123(16) 0.0310(4) Uani d . 1 . .
C C12 0.3430(2) 0.8782(2) 0.44359(17) 0.0372(5) Uani d . 1 . .
H H12 0.3214 0.8790 0.3693 0.045 Uiso calc R 1 . .
C C13 0.4141(2) 0.7834(2) 0.48677(19) 0.0406(5) Uani d . 1 . .
H H13 0.4398 0.7196 0.4414 0.049 Uiso calc R 1 . .
C C14 0.4473(2) 0.7827(2) 0.59658(19) 0.0413(5) Uani d . 1 . .
H H14 0.4940 0.7177 0.6251 0.050 Uiso calc R 1 . .
C C15 0.4114(2) 0.8783(2) 0.66493(18) 0.0361(5) Uani d . 1 . .
H H15 0.4364 0.8785 0.7389 0.043 Uiso calc R 1 . .
C C17 0.0491(2) 0.3758(2) 0.43304(18) 0.0356(5) Uani d . 1 . .
C C19 0.2746(2) 0.4186(2) 0.48183(18) 0.0396(5) Uani d . 1 . .
H H19 0.3484 0.4132 0.5338 0.047 Uiso calc R 1 . .
C C21 0.18924(19) 0.48116(19) 0.32559(15) 0.0282(4) Uani d . 1 . .
C C22 0.05870(19) 0.4349(2) 0.33929(17) 0.0326(5) Uani d . 1 . .
C C24 0.0355(2) 0.5197(2) 0.19095(17) 0.0393(5) Uani d . 1 . .
H H24 -0.0021 0.5484 0.1263 0.047 Uiso calc R 1 . .
C C26 0.39753(18) 0.4774(2) 0.13725(15) 0.0290(4) Uani d . 1 . .
C C27 0.3671(2) 0.3761(2) 0.05959(16) 0.0322(5) Uani d . 1 . .
C C28 0.4589(2) 0.2887(2) 0.04330(18) 0.0429(5) Uani d . 1 . .
H H28 0.4371 0.2224 -0.0090 0.051 Uiso calc R 1 . .
C C29 0.5839(2) 0.3008(3) 0.1056(2) 0.0478(6) Uani d . 1 . .
H H29 0.6455 0.2410 0.0965 0.057 Uiso calc R 1 . .
C C30 0.6173(2) 0.4008(3) 0.1809(2) 0.0495(6) Uani d . 1 . .
H H30 0.7022 0.4093 0.2215 0.059 Uiso calc R 1 . .
C C31 0.5248(2) 0.4892(2) 0.19642(17) 0.0398(5) Uani d . 1 . .
H H31 0.5486 0.5570 0.2471 0.048 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 N9 . . 104.73(9) ?
O1 S1 C10 . . 108.86(9) ?
O2 S1 O1 . . 121.88(10) ?
O2 S1 N9 . . 106.39(9) ?
O2 S1 C10 . . 107.43(9) ?
O3 N16 O4 . . 124.65(19) ?
O3 N16 C11 . . 117.33(18) ?
O4 N16 C11 . . 117.93(18) ?
O5 S2 N25 . . 105.10(8) ?
O5 S2 C26 . . 111.24(9) ?
O6 S2 O5 . . 121.33(10) ?
O6 S2 N25 . . 106.67(9) ?
O6 S2 C26 . . 106.90(10) ?
O7 N32 O8 . . 123.88(19) ?
O7 N32 C27 . . 118.70(17) ?
O8 N32 C27 . . 117.42(18) ?
N2 C1 Cl1 . . 117.83(17) ?
N2 C1 C6 . . 121.4(2) ?
N2 C3 H3 . . 115.9 ?
N4 C3 N2 . . 128.3(2) ?
N4 C3 H3 . . 115.9 ?
N4 C5 N9 . . 128.60(18) ?
N4 C5 C6 . . 126.78(19) ?
N7 C6 C5 . . 111.24(17) ?
N7 C8 N9 . . 113.85(19) ?
N7 C8 H8 . . 123.1 ?
N9 S1 C10 . . 106.61(9) ?
N9 C5 C6 . . 104.60(17) ?
N9 C8 H8 . . 123.1 ?
N18 C17 Cl2 . . 118.10(16) ?
N18 C17 C22 . . 121.22(18) ?
N18 C19 N20 . . 128.4(2) ?
N18 C19 H19 . . 115.8 ?
N20 C19 H19 . . 115.8 ?
N20 C21 N25 . . 128.98(17) ?
N20 C21 C22 . . 126.52(18) ?
N23 C22 C21 . . 111.38(17) ?
N23 C24 N25 . . 114.08(18) ?
N23 C24 H24 . . 123.0 ?
N25 S2 C26 . . 104.22(9) ?
N25 C21 C22 . . 104.48(16) ?
N25 C24 H24 . . 123.0 ?
C1 N2 C3 . . 117.3(2) ?
C1 C6 N7 . . 133.91(19) ?
C1 C6 C5 . . 114.85(19) ?
C5 N4 C3 . . 111.40(19) ?
C5 N9 S1 . . 128.59(14) ?
C5 N9 C8 . . 105.75(16) ?
C6 C1 Cl1 . . 120.78(17) ?
C8 N7 C6 . . 104.56(17) ?
C8 N9 S1 . . 125.05(14) ?
C10 C11 N16 . . 122.06(18) ?
C10 C15 C14 . . 120.1(2) ?
C10 C15 H15 . . 119.9 ?
C11 C10 S1 . . 124.35(16) ?
C11 C12 H12 . . 120.3 ?
C11 C12 C13 . . 119.4(2) ?
C12 C11 N16 . . 116.63(19) ?
C12 C11 C10 . . 121.2(2) ?
C12 C13 H13 . . 119.8 ?
C13 C12 H12 . . 120.3 ?
C13 C14 H14 . . 119.8 ?
C13 C14 C15 . . 120.4(2) ?
C14 C13 C12 . . 120.3(2) ?
C14 C13 H13 . . 119.8 ?
C14 C15 H15 . . 119.9 ?
C15 C10 S1 . . 116.41(15) ?
C15 C10 C11 . . 118.50(19) ?
C15 C14 H14 . . 119.8 ?
C17 N18 C19 . . 117.34(18) ?
C17 C22 N23 . . 133.58(18) ?
C17 C22 C21 . . 115.02(18) ?
C21 N20 C19 . . 111.42(17) ?
C21 N25 S2 . . 128.61(13) ?
C21 N25 C24 . . 105.71(16) ?
C22 C17 Cl2 . . 120.68(17) ?
C24 N23 C22 . . 104.34(17) ?
C24 N25 S2 . . 125.56(14) ?
C26 C27 N32 . . 122.17(18) ?
C26 C31 C30 . . 120.7(2) ?
C26 C31 H31 . . 119.7 ?
C27 C26 S2 . . 126.17(15) ?
C27 C28 H28 . . 120.3 ?
C27 C28 C29 . . 119.3(2) ?
C28 C27 N32 . . 116.2(2) ?
C28 C27 C26 . . 121.6(2) ?
C28 C29 H29 . . 119.9 ?
C29 C28 H28 . . 120.3 ?
C29 C30 H30 . . 119.9 ?
C29 C30 C31 . . 120.3(2) ?
C30 C29 C28 . . 120.2(2) ?
C30 C29 H29 . . 119.9 ?
C30 C31 H31 . . 119.7 ?
C31 C26 S2 . . 115.78(17) ?
C31 C26 C27 . . 117.84(19) ?
C31 C30 H30 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.728(2) ?
Cl2 C17 . 1.720(2) ?
S1 O1 . 1.4226(15) ?
S1 O2 . 1.4178(15) ?
S1 N9 . 1.6794(16) ?
S1 C10 . 1.769(2) ?
S2 O5 . 1.4177(15) ?
S2 O6 . 1.4150(16) ?
S2 N25 . 1.6833(16) ?
S2 C26 . 1.777(2) ?
O3 N16 . 1.216(2) ?
O4 N16 . 1.221(2) ?
O7 N32 . 1.214(2) ?
O8 N32 . 1.217(2) ?
N2 C1 . 1.317(3) ?
N2 C3 . 1.340(3) ?
N4 C3 . 1.336(3) ?
N4 C5 . 1.322(3) ?
N7 C6 . 1.391(3) ?
N7 C8 . 1.293(3) ?
N9 C5 . 1.393(3) ?
N9 C8 . 1.395(3) ?
N16 C11 . 1.471(3) ?
N18 C17 . 1.320(3) ?
N18 C19 . 1.337(3) ?
N20 C19 . 1.339(3) ?
N20 C21 . 1.325(2) ?
N23 C22 . 1.387(3) ?
N23 C24 . 1.290(3) ?
N25 C21 . 1.388(2) ?
N25 C24 . 1.394(3) ?
N32 C27 . 1.468(3) ?
C1 C6 . 1.378(3) ?
C3 H3 . 0.9300 ?
C5 C6 . 1.397(3) ?
C8 H8 . 0.9300 ?
C10 C11 . 1.402(3) ?
C10 C15 . 1.385(3) ?
C11 C12 . 1.374(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.379(3) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.376(3) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.387(3) ?
C15 H15 . 0.9300 ?
C17 C22 . 1.380(3) ?
C19 H19 . 0.9300 ?
C21 C22 . 1.399(3) ?
C24 H24 . 0.9300 ?
C26 C27 . 1.400(3) ?
C26 C31 . 1.385(3) ?
C27 C28 . 1.379(3) ?
C28 H28 . 0.9300 ?
C28 C29 . 1.382(3) ?
C29 H29 . 0.9300 ?
C29 C30 . 1.374(4) ?
C30 H30 . 0.9300 ?
C30 C31 . 1.390(3) ?
C31 H31 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C13 H13 O6 . 0.93 2.60 3.222(3) 125 yes
C15 H15 O2 . 0.93 2.41 2.814(3) 106 ?
C24 H24 O7 2_565 0.93 2.41 3.327(3) 170 yes
C28 H28 O2 1_544 0.93 2.56 3.469(3) 165 yes
C30 H30 N23 1_655 0.93 2.62 3.489(3) 155 yes
C31 H31 O6 . 0.93 2.36 2.794(3) 108 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139080762
