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#$Date: 2024-07-05 18:23:08 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248711.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_7248711
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         'C14 H15 N O2 S'
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'difference Fourier'
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-03-02 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1017(4)
_cell_length_b                   5.7077(2)
_cell_length_c                   25.1568(11)
_cell_measurement_reflns_used    9558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.87
_cell_measurement_theta_min      4.05
_cell_volume                     1306.89(9)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15214
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.980
_diffrn_reflns_theta_min         4.516
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,(Bruker, 2006)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0241
_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)+(0.0281P)²+0.5027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2802
_reflns_number_total             2829
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00309h2.cif
_cod_data_source_block           5b
_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_database_code               7248711
_shelx_shelxl_version_number     2014/7
_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   0.936
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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
S1 S 0.49169(4) 0.44289(7) 0.54283(3) 0.01306(11) Uani 1 1 d . . . . .
O1 O 0.47363(14) 0.6924(2) 0.54517(7) 0.0185(3) Uani 1 1 d . . . . .
O2 O 0.36660(14) 0.2992(2) 0.52983(6) 0.0169(3) Uani 1 1 d . . . . .
N1 N 0.61699(18) 0.3919(3) 0.49885(7) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.6731(3) 0.2051(4) 0.70162(9) 0.0259(5) Uani 1 1 d . . . . .
H1 H 0.7127 0.1551 0.7347 0.031 Uiso 1 1 calc R U . . .
C2 C 0.7201(3) 0.4145(4) 0.67903(9) 0.0245(5) Uani 1 1 d . . . . .
H2 H 0.7918 0.5071 0.6967 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6627(2) 0.4886(4) 0.63097(8) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.6935 0.6326 0.6157 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5590(2) 0.3486(3) 0.60522(8) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.5111(2) 0.1383(4) 0.62710(9) 0.0208(4) Uani 1 1 d . . . . .
H5 H 0.4409 0.0441 0.6091 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5682(3) 0.0688(4) 0.67599(10) 0.0257(5) Uani 1 1 d . . . . .
H6 H 0.5353 -0.0727 0.6919 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6629(2) 0.1461(3) 0.49027(8) 0.0159(4) Uani 1 1 d . . . . .
H7A H 0.5752 0.0458 0.4853 0.019 Uiso 1 1 calc R U . . .
H7B H 0.7174 0.0887 0.5217 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7608(2) 0.1327(4) 0.44096(8) 0.0190(4) Uani 1 1 d . . . . .
H8A H 0.8472 0.2354 0.4463 0.023 Uiso 1 1 calc R U . . .
H8B H 0.7970 -0.0299 0.4369 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6835(2) 0.2043(4) 0.39054(8) 0.0174(4) Uani 1 1 d . . . . .
C10 C 0.7154(3) 0.4159(4) 0.36541(9) 0.0236(5) Uani 1 1 d . . . . .
H10 H 0.7893 0.5156 0.3796 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6398(3) 0.4823(4) 0.31978(9) 0.0299(5) Uani 1 1 d . . . . .
H11 H 0.6627 0.6267 0.3029 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5318(3) 0.3399(5) 0.29878(9) 0.0298(5) Uani 1 1 d . . . . .
H12 H 0.4798 0.3870 0.2678 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4997(2) 0.1275(5) 0.32311(10) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.4260 0.0281 0.3087 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5756(2) 0.0611(4) 0.36848(9) 0.0215(4) Uani 1 1 d . . . . .
H14 H 0.5536 -0.0848 0.3848 0.026 Uiso 1 1 calc R U . . .
H1N H 0.686(3) 0.491(5) 0.5031(11) 0.026(7) Uiso 1 1 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
_geom_angle_publ_flag
O1 S1 O2 118.93(8) . . ?
O1 S1 N1 106.74(9) . . ?
O2 S1 N1 107.44(9) . . ?
O1 S1 C4 107.78(10) . . ?
O2 S1 C4 107.56(9) . . ?
N1 S1 C4 107.97(9) . . ?
C7 N1 S1 118.04(13) . . ?
C7 N1 H1N 116(2) . . ?
S1 N1 H1N 108.5(19) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 S1 120.35(16) . . ?
C3 C4 S1 118.15(16) . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C8 109.28(16) . . ?
N1 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 113.38(16) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C8 120.35(19) . . ?
C10 C9 C8 121.3(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
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
S1 O1 1.4350(13) . ?
S1 O2 1.4409(13) . ?
S1 N1 1.6154(18) . ?
S1 C4 1.769(2) . ?
N1 C7 1.479(2) . ?
N1 H1N 0.86(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.393(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 H14 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
C5 H5 O1 0.95 2.59 3.293(3) 131.1 1_545
C7 H7B O2 0.99 2.61 3.300(2) 127.3 4
N1 H1N S1 0.86(3) 2.98(3) 3.7075(17) 145(2) 4_565
N1 H1N O2 0.86(3) 2.14(3) 2.980(2) 167(3) 4_565
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
O1 S1 N1 C7 177.04(14) . . . . ?
O2 S1 N1 C7 -54.35(17) . . . . ?
C4 S1 N1 C7 61.40(17) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 S1 -178.07(17) . . . . ?
O1 S1 C4 C5 142.31(16) . . . . ?
O2 S1 C4 C5 12.94(19) . . . . ?
N1 S1 C4 C5 -102.73(18) . . . . ?
O1 S1 C4 C3 -38.89(18) . . . . ?
O2 S1 C4 C3 -168.26(15) . . . . ?
N1 S1 C4 C3 76.07(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
S1 C4 C5 C6 179.16(17) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
S1 N1 C7 C8 170.12(14) . . . . ?
N1 C7 C8 C9 -62.7(2) . . . . ?
C7 C8 C9 C14 -70.9(2) . . . . ?
C7 C8 C9 C10 107.8(2) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C10 C9 C14 C13 -1.0(3) . . . . ?
C8 C9 C14 C13 177.8(2) . . . . ?
