#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557619.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_1557619
loop_
_publ_author_name
'Narayan, Easha'
'Fu, Liangfeng'
'Gribble, Gordon W.'
'Kaur, Manpreet'
'Jasinski, Jerry P.'
_publ_section_title
;
 7-Chloro-3-(4-methylphenylsulfonyl)pyrrolo[1,2-c]pyrimidine
;
_journal_coeditor_code           HB4342
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x200382
_journal_paper_doi               10.1107/S241431462000382X
_journal_volume                  5
_journal_year                    2020
_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
;
7-Chloro-3-(4-methylphenylsulfonyl)pyrrolo[1,2-c]pyrimidine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.192(7)
_cell_angle_beta                 99.616(6)
_cell_angle_gamma                104.149(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2285(5)
_cell_length_b                   7.2385(5)
_cell_length_c                   13.7586(11)
_cell_measurement_reflns_used    1885
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.4400
_cell_measurement_theta_min      6.4840
_cell_volume                     663.91(9)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku-Oxford Diffraction Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3839
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.216
_diffrn_reflns_theta_min         3.377
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74818
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.312
_refine_ls_extinction_coef       0.0018(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/1 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2177
_reflns_number_total             2498
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4342sup1.cif
_cod_data_source_block           I
_cod_database_code               1557619
_cod_database_fobs_code          1557619
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.01870(9) 0.02376(9) 0.27155(4) 0.03578(19) Uani d 1 . .
S S1 0.40553(8) 0.62315(7) 0.76558(4) 0.02404(18) Uani d 1 . .
O O1 0.5458(3) 0.7802(2) 0.74516(13) 0.0334(4) Uani d 1 . .
O O2 0.2700(3) 0.6692(3) 0.82618(13) 0.0340(4) Uani d 1 . .
N N1 0.3648(3) 0.4137(3) 0.57537(14) 0.0250(4) Uani d 1 . .
N N2 0.0639(3) 0.2272(3) 0.46404(13) 0.0216(4) Uani d 1 . .
C C1 0.2605(3) 0.4612(3) 0.64732(16) 0.0221(4) Uani d 1 . .
C C2 0.0627(3) 0.3971(3) 0.63311(16) 0.0231(4) Uani d 1 . .
H H2 0.001144 0.434521 0.685034 0.028 Uiso calc 1 . .
C C3 -0.0462(3) 0.2721(3) 0.53723(17) 0.0228(4) Uani d 1 . .
C C4 -0.2410(3) 0.1749(3) 0.49171(18) 0.0282(5) Uani d 1 . .
H H4 -0.346453 0.178047 0.521972 0.034 Uiso calc 1 . .
C C5 -0.2517(3) 0.0705(3) 0.39148(18) 0.0289(5) Uani d 1 . .
H H5 -0.365477 -0.008063 0.343710 0.035 Uiso calc 1 . .
C C6 -0.0663(3) 0.1047(3) 0.37665(16) 0.0257(5) Uani d 1 . .
C C7 0.2645(3) 0.3009(3) 0.48672(16) 0.0235(4) Uani d 1 . .
H H7 0.331004 0.268421 0.436325 0.028 Uiso calc 1 . .
C C8 0.5354(3) 0.4809(3) 0.82241(16) 0.0253(4) Uani d 1 . .
C C9 0.7327(4) 0.5134(3) 0.82356(17) 0.0293(5) Uani d 1 . .
H H9 0.796540 0.608266 0.794615 0.035 Uiso calc 1 . .
C C10 0.8339(4) 0.4003(4) 0.86927(19) 0.0316(5) Uani d 1 . .
H H10 0.966752 0.421378 0.871207 0.038 Uiso calc 1 . .
C C11 0.7390(4) 0.2571(3) 0.91184(16) 0.0269(5) Uani d 1 . .
C C12 0.5414(4) 0.2299(4) 0.90997(19) 0.0331(5) Uani d 1 . .
H H12 0.476588 0.134692 0.938446 0.040 Uiso calc 1 . .
C C13 0.4392(4) 0.3421(4) 0.86641(19) 0.0326(5) Uani d 1 . .
H H13 0.307487 0.324508 0.866706 0.039 Uiso calc 1 . .
C C14 0.8477(4) 0.1336(4) 0.95979(18) 0.0335(5) Uani d 1 . .
H H14A 0.794694 -0.002190 0.921296 0.050 Uiso calc 1 . .
H H14B 0.833361 0.145628 1.028789 0.050 Uiso calc 1 . .
H H14C 0.984104 0.178670 0.959859 0.050 Uiso calc 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'
Cl Cl 0.3639 0.7018 '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'
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 . . 119.68(11) ?
O1 S1 C1 . . 108.51(10) ?
O1 S1 C8 . . 107.90(11) ?
O2 S1 C1 . . 106.24(11) ?
O2 S1 C8 . . 108.56(11) ?
C8 S1 C1 . . 105.03(10) ?
C7 N1 C1 . . 116.87(19) ?
C6 N2 C3 . . 107.32(18) ?
C6 N2 C7 . . 131.24(19) ?
C7 N2 C3 . . 121.44(18) ?
N1 C1 S1 . . 114.68(16) ?
C2 C1 S1 . . 119.95(16) ?
C2 C1 N1 . . 125.37(19) ?
C1 C2 C3 . . 117.78(19) ?
C2 C3 N2 . . 115.87(19) ?
C4 C3 N2 . . 107.3(2) ?
C4 C3 C2 . . 136.8(2) ?
C3 C4 C5 . . 107.8(2) ?
C6 C5 C4 . . 108.0(2) ?
N2 C6 Cl1 . . 119.51(18) ?
C5 C6 Cl1 . . 130.89(18) ?
C5 C6 N2 . . 109.6(2) ?
N1 C7 N2 . . 122.67(19) ?
C9 C8 S1 . . 119.13(17) ?
C13 C8 S1 . . 119.48(18) ?
C13 C8 C9 . . 121.4(2) ?
C8 C9 C10 . . 118.5(2) ?
C11 C10 C9 . . 121.1(2) ?
C10 C11 C14 . . 121.0(2) ?
C12 C11 C10 . . 118.8(2) ?
C12 C11 C14 . . 120.2(2) ?
C13 C12 C11 . . 121.1(2) ?
C8 C13 C12 . . 119.2(2) ?
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 C6 . 1.711(2) ?
S1 O1 . 1.4370(18) ?
S1 O2 . 1.4429(18) ?
S1 C1 . 1.773(2) ?
S1 C8 . 1.767(2) ?
N1 C1 . 1.378(3) ?
N1 C7 . 1.294(3) ?
N2 C3 . 1.417(3) ?
N2 C6 . 1.371(3) ?
N2 C7 . 1.373(3) ?
C1 C2 . 1.358(3) ?
C2 C3 . 1.407(3) ?
C3 C4 . 1.380(3) ?
C4 C5 . 1.405(3) ?
C5 C6 . 1.360(3) ?
C8 C9 . 1.384(3) ?
C8 C13 . 1.384(3) ?
C9 C10 . 1.399(3) ?
C10 C11 . 1.390(3) ?
C11 C12 . 1.389(4) ?
C11 C14 . 1.507(3) ?
C12 C13 . 1.384(4) ?
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
C14 H14B O2 2_667 0.96 2.49 3.329(3) 146 yes
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
S1 C1 C2 C3 . . . . 178.70(15) ?
S1 C8 C9 C10 . . . . 179.69(17) ?
S1 C8 C13 C12 . . . . 179.40(19) ?
O1 S1 C1 N1 . . . . 44.81(18) ?
O1 S1 C1 C2 . . . . -134.12(16) ?
O1 S1 C8 C9 . . . . -10.4(2) ?
O1 S1 C8 C13 . . . . 168.42(19) ?
O2 S1 C1 N1 . . . . 174.70(15) ?
O2 S1 C1 C2 . . . . -4.23(19) ?
O2 S1 C8 C9 . . . . -141.51(19) ?
O2 S1 C8 C13 . . . . 37.3(2) ?
N1 C1 C2 C3 . . . . -0.1(3) ?
N2 C3 C4 C5 . . . . 0.2(2) ?
C1 S1 C8 C9 . . . . 105.19(19) ?
C1 S1 C8 C13 . . . . -76.0(2) ?
C1 N1 C7 N2 . . . . -1.1(3) ?
C1 C2 C3 N2 . . . . -0.6(3) ?
C1 C2 C3 C4 . . . . 179.2(2) ?
C2 C3 C4 C5 . . . . -179.7(2) ?
C3 N2 C6 Cl1 . . . . 179.28(14) ?
C3 N2 C6 C5 . . . . -0.1(2) ?
C3 N2 C7 N1 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
C4 C5 C6 Cl1 . . . . -179.09(17) ?
C4 C5 C6 N2 . . . . 0.2(2) ?
C6 N2 C3 C2 . . . . 179.87(17) ?
C6 N2 C3 C4 . . . . 0.0(2) ?
C6 N2 C7 N1 . . . . -178.8(2) ?
C7 N1 C1 S1 . . . . -177.86(15) ?
C7 N1 C1 C2 . . . . 1.0(3) ?
C7 N2 C3 C2 . . . . 0.5(3) ?
C7 N2 C3 C4 . . . . -179.37(18) ?
C7 N2 C6 Cl1 . . . . -1.5(3) ?
C7 N2 C6 C5 . . . . 179.1(2) ?
C8 S1 C1 N1 . . . . -70.37(17) ?
C8 S1 C1 C2 . . . . 110.70(18) ?
C8 C9 C10 C11 . . . . 0.6(4) ?
C9 C8 C13 C12 . . . . -1.8(4) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
C9 C10 C11 C14 . . . . 179.2(2) ?
C10 C11 C12 C13 . . . . 0.2(4) ?
C11 C12 C13 C8 . . . . 1.2(4) ?
C13 C8 C9 C10 . . . . 0.9(3) ?
C14 C11 C12 C13 . . . . 179.9(2) ?
