#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:23:08 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248717.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_7248717
loop_
_publ_author_name
'Shaikh, Samir R.'
'Gawade, Rupesh L.'
'Dabke, Niteen B.'
'Dash, Soumya R.'
'Vanka, Kumar'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Crystal engineering for intramolecular π--π stacking: effect of
 substitution of electron-donating and electron-withdrawing groups on the
 molecular geometry in conformationally flexible Sulfoesters and
 sulfonamides
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              3557
_journal_page_last               3573
_journal_paper_doi               10.1039/D4CE00309H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C13 H13 Cl N2 O2 S'
_chemical_formula_sum            'C13 H13 Cl N2 O2 S'
_chemical_formula_weight         296.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.423(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.225(3)
_cell_length_b                   7.0381(14)
_cell_length_c                   14.882(3)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      3.20
_cell_volume                     1334.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41523
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.512
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0358P)²+0.5479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3842
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00309h2.cif
_cod_data_source_block           3c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7248707--7248724.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248717
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.843
_shelx_estimated_absorpt_t_max   0.905
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.63166(2) 0.29078(4) 0.53211(2) 0.02379(7) Uani 1 1 d . . . . .
S1 S 0.27845(2) 0.29593(3) 0.67376(2) 0.01540(6) Uani 1 1 d . . . . .
O1 O 0.23769(6) 0.10519(10) 0.66082(6) 0.02323(15) Uani 1 1 d . . . . .
O2 O 0.31992(6) 0.38385(12) 0.77104(5) 0.02377(15) Uani 1 1 d . . . . .
N1 N 0.18389(6) 0.42437(11) 0.59577(6) 0.01486(14) Uani 1 1 d . . . . .
H1N H 0.1500(12) 0.372(2) 0.5392(11) 0.030(4) Uiso 1 1 d . . . . .
N2 N -0.05543(6) 0.68863(11) 0.60894(6) 0.01593(14) Uani 1 1 d . . . . .
C1 C 0.53454(7) 0.29127(13) 0.57299(7) 0.01678(16) Uani 1 1 d . . . . .
C2 C 0.43842(7) 0.20700(13) 0.51237(7) 0.01772(17) Uani 1 1 d . . . . .
H2 H 0.426126 0.150304 0.450171 0.021 Uiso 1 1 calc R U . . .
C3 C 0.36094(7) 0.20784(13) 0.54506(7) 0.01640(16) Uani 1 1 d . . . . .
H3 H 0.295010 0.149569 0.505614 0.020 Uiso 1 1 calc R U . . .
C4 C 0.38013(7) 0.29452(12) 0.63606(6) 0.01412(15) Uani 1 1 d . . . . .
C5 C 0.47660(7) 0.37878(13) 0.69582(7) 0.01727(16) Uani 1 1 d . . . . .
H5 H 0.488744 0.437308 0.757558 0.021 Uiso 1 1 calc R U . . .
C6 C 0.55520(7) 0.37627(13) 0.66398(7) 0.01857(17) Uani 1 1 d . . . . .
H6 H 0.621772 0.431863 0.703972 0.022 Uiso 1 1 calc R U . . .
C7 C 0.19505(7) 0.63128(13) 0.59156(7) 0.01587(16) Uani 1 1 d . . . . .
H7A H 0.217916 0.663302 0.539540 0.019 Uiso 1 1 calc R U . . .
H7B H 0.249006 0.677975 0.656992 0.019 Uiso 1 1 calc R U . . .
C8 C 0.08988(7) 0.72684(13) 0.56681(6) 0.01523(15) Uani 1 1 d . . . . .
H8A H 0.097211 0.865160 0.559574 0.018 Uiso 1 1 calc R U . . .
H8B H 0.036955 0.678414 0.501304 0.018 Uiso 1 1 calc R U . . .
C9 C 0.04964(7) 0.69553(12) 0.64421(6) 0.01354(15) Uani 1 1 d . . . . .
C10 C 0.11666(7) 0.67953(14) 0.74637(7) 0.01808(17) Uani 1 1 d . . . . .
H10 H 0.190606 0.682600 0.769667 0.022 Uiso 1 1 calc R U . . .
C11 C 0.07421(8) 0.65905(14) 0.81381(7) 0.01942(17) Uani 1 1 d . . . . .
H11 H 0.118869 0.647702 0.883644 0.023 Uiso 1 1 calc R U . . .
C12 C -0.03376(8) 0.65534(13) 0.77824(7) 0.01852(17) Uani 1 1 d . . . . .
H12 H -0.064840 0.643606 0.822774 0.022 Uiso 1 1 calc R U . . .
C13 C -0.09510(7) 0.66932(14) 0.67533(7) 0.01887(17) Uani 1 1 d . . . . .
H13 H -0.169235 0.665007 0.650408 0.023 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 '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
_geom_angle_publ_flag
O2 S1 O1 119.73(5) . . ?
O2 S1 N1 108.75(4) . . ?
O1 S1 N1 105.65(4) . . ?
O2 S1 C4 107.15(4) . . ?
O1 S1 C4 106.84(4) . . ?
N1 S1 C4 108.29(4) . . ?
C7 N1 S1 121.10(6) . . ?
C7 N1 H1N 114.6(11) . . ?
S1 N1 H1N 113.2(11) . . ?
C13 N2 C9 118.23(8) . . ?
C6 C1 C2 122.47(8) . . ?
C6 C1 Cl1 119.08(7) . . ?
C2 C1 Cl1 118.45(7) . . ?
C3 C2 C1 118.36(8) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.88(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.13(8) . . ?
C5 C4 S1 120.50(7) . . ?
C3 C4 S1 118.37(7) . . ?
C4 C5 C6 119.25(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 118.91(8) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 C8 109.49(7) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 114.44(7) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 121.60(8) . . ?
N2 C9 C8 116.03(8) . . ?
C10 C9 C8 122.35(8) . . ?
C11 C10 C9 119.33(9) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.37(8) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 117.80(8) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
N2 C13 C12 123.66(9) . . ?
N2 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7398(10) . ?
S1 O2 1.4377(8) . ?
S1 O1 1.4409(8) . ?
S1 N1 1.6076(8) . ?
S1 C4 1.7689(9) . ?
N1 C7 1.4692(12) . ?
N1 H1N 0.847(16) . ?
N2 C13 1.3451(12) . ?
N2 C9 1.3467(11) . ?
C1 C6 1.3870(13) . ?
C1 C2 1.3919(13) . ?
C2 C3 1.3888(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3970(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3927(12) . ?
C5 C6 1.3951(13) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5283(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5133(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3940(12) . ?
C10 C11 1.3900(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.3843(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3882(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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
_geom_hbond_publ_flag
N1 H1N N2 0.847(16) 2.052(16) 2.8807(12) 165.8(16) 3_566 yes
C12 H12 O1 0.95 2.59 3.4213(13) 146.2 2_556 yes
C8 H8A O1 0.99 2.54 3.2941(13) 133.1 1_565 yes
C7 H7A Cl1 0.99 2.80 3.7152(10) 153.7 3_666 yes
C6 H6 O1 0.95 2.44 3.3522(12) 160.9 2_656 yes
C2 H2 O2 0.95 2.42 3.2803(13) 150.3 4_565 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C7 46.95(8) . . . . ?
O1 S1 N1 C7 176.67(7) . . . . ?
C4 S1 N1 C7 -69.16(7) . . . . ?
C6 C1 C2 C3 -0.34(14) . . . . ?
Cl1 C1 C2 C3 -179.89(7) . . . . ?
C1 C2 C3 C4 0.97(13) . . . . ?
C2 C3 C4 C5 -0.81(13) . . . . ?
C2 C3 C4 S1 178.91(7) . . . . ?
O2 S1 C4 C5 -3.17(9) . . . . ?
O1 S1 C4 C5 -132.64(7) . . . . ?
N1 S1 C4 C5 113.98(8) . . . . ?
O2 S1 C4 C3 177.10(7) . . . . ?
O1 S1 C4 C3 47.64(8) . . . . ?
N1 S1 C4 C3 -65.74(8) . . . . ?
C3 C4 C5 C6 0.00(13) . . . . ?
S1 C4 C5 C6 -179.71(7) . . . . ?
C2 C1 C6 C5 -0.46(14) . . . . ?
Cl1 C1 C6 C5 179.08(7) . . . . ?
C4 C5 C6 C1 0.62(13) . . . . ?
S1 N1 C7 C8 -145.35(6) . . . . ?
N1 C7 C8 C9 62.25(9) . . . . ?
C13 N2 C9 C10 1.25(13) . . . . ?
C13 N2 C9 C8 -177.16(8) . . . . ?
C7 C8 C9 N2 -148.05(8) . . . . ?
C7 C8 C9 C10 33.55(12) . . . . ?
N2 C9 C10 C11 -1.06(14) . . . . ?
C8 C9 C10 C11 177.25(8) . . . . ?
C9 C10 C11 C12 -0.14(14) . . . . ?
C10 C11 C12 C13 1.05(14) . . . . ?
C9 N2 C13 C12 -0.26(14) . . . . ?
C11 C12 C13 N2 -0.89(15) . . . . ?
