#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224126.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_2224126
loop_
_publ_author_name
'Selig, Roland'
'Schollmeyer, Dieter'
'Albrecht, Wolfgang'
'Laufer, Stefan'
_publ_section_title
;
 4-Chloro-1-(4-methylphenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
;
_journal_coeditor_code           BT5113
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3018
_journal_paper_doi               10.1107/S1600536809044559
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H11 Cl N2 O2 S'
_chemical_formula_moiety         'C14 H11 Cl N2 O2 S'
_chemical_formula_sum            'C14 H11 Cl N2 O2 S'
_chemical_formula_weight         306.76
_chemical_name_systematic
;
4-Chloro-1-(4-methylphenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
;
_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                 91.531(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.7342(12)
_cell_length_b                   7.6313(2)
_cell_length_c                   16.4649(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      70
_cell_measurement_theta_min      65
_cell_volume                     2729.9(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2580
_diffrn_reflns_theta_full        69.90
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.936
_exptl_absorpt_correction_T_max  0.5191
_exptl_absorpt_correction_T_min  0.3190
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(PLATON; Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0425
_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)+(0.0708P)²+2.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1178
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2435
_reflns_number_total             2580
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5113.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224126
_cod_database_fobs_code          2224126
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_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
S S1 0.37591(3) 0.21601(7) 0.24460(3) 0.04415(18) Uani d . 1 . .
Cl Cl1 0.17076(3) 0.02839(8) 0.52042(4) 0.0552(2) Uani d . 1 . .
O O1 0.35059(9) 0.2966(2) 0.17315(9) 0.0568(4) Uani d . 1 . .
O O2 0.40887(9) 0.0548(2) 0.23960(10) 0.0574(4) Uani d . 1 . .
N N1 0.31423(8) 0.1778(2) 0.30138(10) 0.0419(4) Uani d . 1 . .
C C2 0.25596(11) 0.2537(3) 0.28739(14) 0.0471(5) Uani d . 1 . .
H H2 0.2448 0.3249 0.2420 0.057 Uiso calc R 1 . .
C C3 0.21846(10) 0.2106(3) 0.34773(14) 0.0452(5) Uani d . 1 . .
H H3 0.1766 0.2440 0.3520 0.054 Uiso calc R 1 . .
C C3A 0.25318(9) 0.1048(3) 0.40466(12) 0.0393(4) Uani d . 1 . .
C C4 0.24293(10) 0.0231(3) 0.47865(13) 0.0428(5) Uani d . 1 . .
C C5 0.29115(11) -0.0600(3) 0.51803(13) 0.0463(5) Uani d . 1 . .
H H5 0.2853 -0.1165 0.5686 0.056 Uiso calc R 1 . .
C C6 0.34872(11) -0.0608(3) 0.48308(13) 0.0458(5) Uani d . 1 . .
H H6 0.3814 -0.1178 0.5120 0.055 Uiso calc R 1 . .
N N7 0.36143(8) 0.0130(2) 0.41150(11) 0.0427(4) Uani d . 1 . .
C C7A 0.31332(9) 0.0897(2) 0.37609(12) 0.0374(4) Uani d . 1 . .
C C8 0.41925(9) 0.3694(3) 0.30021(11) 0.0381(4) Uani d . 1 . .
C C9 0.40403(10) 0.5448(3) 0.29162(14) 0.0466(5) Uani d . 1 . .
H H9 0.3696 0.5785 0.2585 0.056 Uiso calc R 1 . .
C C10 0.43905(10) 0.6698(3) 0.33118(14) 0.0478(5) Uani d . 1 . .
H H10 0.4284 0.7899 0.3252 0.057 Uiso calc R 1 . .
C C11 0.48956(9) 0.6237(3) 0.37969(12) 0.0434(5) Uani d . 1 . .
C C12 0.50321(10) 0.4468(3) 0.38851(14) 0.0484(5) Uani d . 1 . .
H H12 0.5373 0.4129 0.4223 0.058 Uiso calc R 1 . .
C C13 0.46853(10) 0.3189(3) 0.34933(13) 0.0451(5) Uani d . 1 . .
H H13 0.4785 0.1985 0.3561 0.054 Uiso calc R 1 . .
C C14 0.52904(13) 0.7648(4) 0.41851(17) 0.0615(6) Uani d . 1 . .
H H14A 0.5628 0.7105 0.4502 0.092 Uiso calc R 1 . .
H H14B 0.5040 0.8362 0.4544 0.092 Uiso calc R 1 . .
H H14C 0.5461 0.8392 0.3761 0.092 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 O2 . . 120.52(10) ?
O1 S1 N1 . . 103.77(10) ?
O2 S1 N1 . . 106.95(10) ?
O1 S1 C8 . . 109.55(10) ?
O2 S1 C8 . . 110.09(10) ?
N1 S1 C8 . . 104.58(9) ?
C7A N1 C2 . . 107.91(18) ?
C7A N1 S1 . . 126.97(15) ?
C2 N1 S1 . . 124.46(16) ?
C3 C2 N1 . . 109.85(19) ?
C3 C2 H2 . . 125.1 ?
N1 C2 H2 . . 125.1 ?
C2 C3 C3A . . 107.59(19) ?
C2 C3 H3 . . 126.2 ?
C3A C3 H3 . . 126.2 ?
C4 C3A C7A . . 115.35(19) ?
C4 C3A C3 . . 136.9(2) ?
C7A C3A C3 . . 107.75(19) ?
C5 C4 C3A . . 118.8(2) ?
C5 C4 Cl1 . . 120.78(17) ?
C3A C4 Cl1 . . 120.37(17) ?
C4 C5 C6 . . 119.4(2) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
N7 C6 C5 . . 124.8(2) ?
N7 C6 H6 . . 117.6 ?
C5 C6 H6 . . 117.6 ?
C7A N7 C6 . . 113.26(19) ?
N7 C7A N1 . . 124.77(19) ?
N7 C7A C3A . . 128.40(19) ?
N1 C7A C3A . . 106.81(17) ?
C13 C8 C9 . . 120.6(2) ?
C13 C8 S1 . . 121.32(17) ?
C9 C8 S1 . . 118.05(16) ?
C10 C9 C8 . . 119.7(2) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 121.2(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C12 . . 118.1(2) ?
C10 C11 C14 . . 119.7(2) ?
C12 C11 C14 . . 122.1(2) ?
C13 C12 C11 . . 121.7(2) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C8 C13 C12 . . 118.8(2) ?
C8 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
S1 O1 . 1.4250(16) ?
S1 O2 . 1.4269(17) ?
S1 N1 . 1.6803(18) ?
S1 C8 . 1.746(2) ?
Cl1 C4 . 1.730(2) ?
N1 C7A . 1.402(3) ?
N1 C2 . 1.406(3) ?
C2 C3 . 1.343(3) ?
C2 H2 . 0.9500 ?
C3 C3A . 1.436(3) ?
C3 H3 . 0.9500 ?
C3A C4 . 1.392(3) ?
C3A C7A . 1.406(3) ?
C4 C5 . 1.373(3) ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9500 ?
C6 N7 . 1.342(3) ?
C6 H6 . 0.9500 ?
N7 C7A . 1.320(3) ?
C8 C13 . 1.380(3) ?
C8 C9 . 1.385(3) ?
C9 C10 . 1.374(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.386(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.389(3) ?
C11 C14 . 1.508(3) ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C7A . . . . 175.64(17) ?
O2 S1 N1 C7A . . . . 47.22(19) ?
C8 S1 N1 C7A . . . . -69.55(19) ?
O1 S1 N1 C2 . . . . -14.9(2) ?
O2 S1 N1 C2 . . . . -143.28(18) ?
C8 S1 N1 C2 . . . . 99.95(18) ?
C7A N1 C2 C3 . . . . -2.7(2) ?
S1 N1 C2 C3 . . . . -173.92(15) ?
N1 C2 C3 C3A . . . . 1.0(2) ?
C2 C3 C3A C4 . . . . 178.3(2) ?
C2 C3 C3A C7A . . . . 1.0(2) ?
C7A C3A C4 C5 . . . . 1.5(3) ?
C3 C3A C4 C5 . . . . -175.7(2) ?
C7A C3A C4 Cl1 . . . . -179.07(14) ?
C3 C3A C4 Cl1 . . . . 3.8(3) ?
C3A C4 C5 C6 . . . . -0.1(3) ?
Cl1 C4 C5 C6 . . . . -179.55(16) ?
C4 C5 C6 N7 . . . . -0.9(3) ?
C5 C6 N7 C7A . . . . 0.3(3) ?
C6 N7 C7A N1 . . . . 179.39(18) ?
C6 N7 C7A C3A . . . . 1.4(3) ?
C2 N1 C7A N7 . . . . -175.14(19) ?
S1 N1 C7A N7 . . . . -4.2(3) ?
C2 N1 C7A C3A . . . . 3.3(2) ?
S1 N1 C7A C3A . . . . 174.17(14) ?
C4 C3A C7A N7 . . . . -2.3(3) ?
C3 C3A C7A N7 . . . . 175.68(19) ?
C4 C3A C7A N1 . . . . 179.38(16) ?
C3 C3A C7A N1 . . . . -2.6(2) ?
O1 S1 C8 C13 . . . . -151.45(17) ?
O2 S1 C8 C13 . . . . -16.72(19) ?
N1 S1 C8 C13 . . . . 97.86(17) ?
O1 S1 C8 C9 . . . . 26.4(2) ?
O2 S1 C8 C9 . . . . 161.17(17) ?
N1 S1 C8 C9 . . . . -84.25(18) ?
C13 C8 C9 C10 . . . . 1.2(3) ?
S1 C8 C9 C10 . . . . -176.68(17) ?
C8 C9 C10 C11 . . . . 0.0(3) ?
C9 C10 C11 C12 . . . . -1.2(3) ?
C9 C10 C11 C14 . . . . 176.6(2) ?
C10 C11 C12 C13 . . . . 1.1(3) ?
C14 C11 C12 C13 . . . . -176.7(2) ?
C9 C8 C13 C12 . . . . -1.3(3) ?
S1 C8 C13 C12 . . . . 176.54(17) ?
C11 C12 C13 C8 . . . . 0.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6469158
2 PubChem 8167268
