#------------------------------------------------------------------------------
#$Date: 2021-08-12 01:45:52 +0300 (Thu, 12 Aug 2021) $
#$Revision: 268034 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243360.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_7243360
loop_
_publ_author_name
'Kowalik, Mateusz'
'Brzeski, Jakub'
'Gawrońska, Małgorzata'
'Kazimierczuk, Katarzyna'
'Makowski, Mariusz'
_publ_section_title
;
 Experimental and theoretical investigation of conformational states and
 noncovalent interactions in crystalline sulfonamides with a methoxyphenyl
 moiety
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE00869B
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13  H14  N2  O3  S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_name_systematic
;
 4-Amino-N-(3-methoxyphenyl)benzenesulfonamide
;
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2020-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-03-02 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.0734(4)
_cell_length_b                   15.4472(10)
_cell_length_c                   27.066(2)
_cell_measurement_reflns_used    4620
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.67
_cell_measurement_wavelength     0.71073
_cell_volume                     2539.3(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32247
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.247
_diffrn_reflns_theta_min         2.637
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²+1.4252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0
_reflns_number_gt                3073
_reflns_number_total             3418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00869b2.cif
_cod_data_source_block           ug2_2020
_cod_database_code               7243360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.43254(18) 0.43963(7) 0.67788(4) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.63898(18) 0.45165(7) 0.69955(4) 0.0187(2) Uani 1 1 d . . . . .
H2 H 0.72038 0.403359 0.711338 0.022 Uiso 1 1 calc R U . . .
C3 C 0.72400(19) 0.53437(7) 0.70373(4) 0.0195(2) Uani 1 1 d . . . . .
H3 H 0.86383 0.542804 0.718703 0.023 Uiso 1 1 calc R U . . .
C4 C 0.60546(19) 0.60606(7) 0.68603(4) 0.0175(2) Uani 1 1 d . . . . .
C5 C 0.39949(19) 0.59271(7) 0.66376(4) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.318724 0.64067 0.651345 0.023 Uiso 1 1 calc R U . . .
C6 C 0.31327(18) 0.50985(7) 0.65980(4) 0.0184(2) Uani 1 1 d . . . . .
H6 H 0.173571 0.501033 0.644835 0.022 Uiso 1 1 calc R U . . .
C7 C 0.48780(18) 0.31609(7) 0.58195(4) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.68924(18) 0.30012(8) 0.55874(4) 0.0200(2) Uani 1 1 d . . . . .
H8 H 0.803347 0.270309 0.575676 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7201(2) 0.32845(8) 0.51060(4) 0.0215(2) Uani 1 1 d . . . . .
H9 H 0.85589 0.316803 0.494486 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5565(2) 0.37361(8) 0.48537(4) 0.0211(2) Uani 1 1 d . . . . .
H10 H 0.580142 0.393148 0.452519 0.025 Uiso 1 1 calc R U . . .
C11 C 0.35770(19) 0.38953(7) 0.50925(4) 0.0189(2) Uani 1 1 d . . . . .
C12 C 0.32156(18) 0.36014(7) 0.55754(4) 0.0181(2) Uani 1 1 d . . . . .
H12 H 0.184409 0.370316 0.573384 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1990(2) 0.45896(9) 0.43883(4) 0.0272(3) Uani 1 1 d . . . . .
H13A H 0.219034 0.408049 0.417703 0.041 Uiso 1 1 calc R U . . .
H13B H 0.325176 0.497935 0.434938 0.041 Uiso 1 1 calc R U . . .
H13C H 0.063811 0.489268 0.429285 0.041 Uiso 1 1 calc R U . . .
N1 N 0.69409(18) 0.68914(7) 0.68928(4) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.45733(17) 0.28289(6) 0.63075(4) 0.01806(19) Uani 1 1 d . . . . .
O1 O 0.37532(15) 0.28789(5) 0.71848(3) 0.02276(18) Uani 1 1 d . . . . .
O2 O 0.09681(14) 0.34242(5) 0.65946(3) 0.02137(18) Uani 1 1 d . . . . .
O3 O 0.18315(14) 0.43224(6) 0.48916(3) 0.02447(19) Uani 1 1 d . . . . .
S1 S 0.32378(4) 0.33486(2) 0.67398(2) 0.01650(8) Uani 1 1 d . . . . .
H1B H 0.786(3) 0.6968(12) 0.7152(7) 0.037(5) Uiso 1 1 d . . . . .
H2A H 0.568(3) 0.2545(11) 0.6427(6) 0.030(4) Uiso 1 1 d . . . . .
H1A H 0.601(3) 0.7303(12) 0.6872(6) 0.032(4) 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 0 '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 0.006 '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
C6 C1 C2 120.72(10) . . ?
C6 C1 S1 120.15(9) . . ?
C2 C1 S1 119.13(8) . . ?
C3 C2 C1 119.49(10) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.61(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C5 120.42(10) . . ?
N1 C4 C3 120.40(11) . . ?
C5 C4 C3 119.15(10) . . ?
C6 C5 C4 120.35(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.67(10) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 120.69(10) . . ?
C12 C7 N2 121.52(10) . . ?
C8 C7 N2 117.75(10) . . ?
C9 C8 C7 119.02(11) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.46(11) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.68(11) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
O3 C11 C10 125.14(10) . . ?
O3 C11 C12 114.05(10) . . ?
C10 C11 C12 120.80(11) . . ?
C7 C12 C11 119.34(10) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 H1B 114.1(12) . . ?
C4 N1 H1A 115.1(12) . . ?
H1B N1 H1A 111.4(17) . . ?
C7 N2 S1 123.34(8) . . ?
C7 N2 H2A 115.4(11) . . ?
S1 N2 H2A 111.5(11) . . ?
C11 O3 C13 117.96(10) . . ?
O2 S1 O1 118.53(5) . . ?
O2 S1 N2 108.66(5) . . ?
O1 S1 N2 104.08(5) . . ?
O2 S1 C1 107.64(5) . . ?
O1 S1 C1 109.46(5) . . ?
N2 S1 C1 108.05(5) . . ?
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
C1 C6 1.3931(15) . ?
C1 C2 1.3967(15) . ?
C1 S1 1.7511(11) . ?
C2 C3 1.3828(16) . ?
C2 H2 0.95 . ?
C3 C4 1.4051(16) . ?
C3 H3 0.95 . ?
C4 N1 1.3944(15) . ?
C4 C5 1.4038(16) . ?
C5 C6 1.3870(16) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.3853(15) . ?
C7 C8 1.3972(15) . ?
C7 N2 1.4289(14) . ?
C8 C9 1.3872(16) . ?
C8 H8 0.95 . ?
C9 C10 1.3931(17) . ?
C9 H9 0.95 . ?
C10 C11 1.3913(16) . ?
C10 H10 0.95 . ?
C11 O3 1.3618(14) . ?
C11 C12 1.4008(15) . ?
C12 H12 0.95 . ?
C13 O3 1.4267(14) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
N1 H1B 0.904(19) . ?
N1 H1A 0.853(19) . ?
N2 S1 1.6344(10) . ?
N2 H2A 0.865(18) . ?
O1 S1 1.4405(9) . ?
O2 S1 1.4382(9) . ?
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
C12 H12 O2 0.95 2.43 3.0899(14) 126.6 .
N1 H1B O1 0.904(19) 2.484(19) 2.9559(13) 113.0(14) 3_656
N1 H1B O1 0.904(19) 2.493(19) 3.1289(14) 127.7(15) 8_765
N2 H2A N1 0.865(18) 2.167(18) 3.0148(15) 166.4(16) 8_755
N1 H1A O2 0.853(19) 2.237(19) 3.0626(14) 162.8(16) 8_665
C12 H12 O2 0.95 2.43 3.0899(14) 126.6 .
N1 H1B O1 0.904(19) 2.484(19) 2.9559(13) 113.0(14) 3_656
N1 H1B O1 0.904(19) 2.493(19) 3.1289(14) 127.7(15) 8_765
N2 H2A N1 0.865(18) 2.167(18) 3.0148(15) 166.4(16) 8_755
N1 H1A O2 0.853(19) 2.237(19) 3.0626(14) 162.8(16) 8_665
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
C6 C1 C2 C3 0.97(16) . . . . ?
S1 C1 C2 C3 -178.63(9) . . . . ?
C1 C2 C3 C4 -0.52(17) . . . . ?
C2 C3 C4 N1 -178.51(10) . . . . ?
C2 C3 C4 C5 -0.30(17) . . . . ?
N1 C4 C5 C6 178.90(11) . . . . ?
C3 C4 C5 C6 0.69(16) . . . . ?
C4 C5 C6 C1 -0.25(17) . . . . ?
C2 C1 C6 C5 -0.59(17) . . . . ?
S1 C1 C6 C5 179.01(9) . . . . ?
C12 C7 C8 C9 -0.51(17) . . . . ?
N2 C7 C8 C9 177.35(10) . . . . ?
C7 C8 C9 C10 1.13(17) . . . . ?
C8 C9 C10 C11 -0.59(17) . . . . ?
C9 C10 C11 O3 -179.59(11) . . . . ?
C9 C10 C11 C12 -0.58(17) . . . . ?
C8 C7 C12 C11 -0.62(16) . . . . ?
N2 C7 C12 C11 -178.40(10) . . . . ?
O3 C11 C12 C7 -179.70(10) . . . . ?
C10 C11 C12 C7 1.18(17) . . . . ?
C12 C7 N2 S1 -39.58(15) . . . . ?
C8 C7 N2 S1 142.58(9) . . . . ?
C10 C11 O3 C13 3.58(17) . . . . ?
C12 C11 O3 C13 -175.50(10) . . . . ?
C7 N2 S1 O2 65.08(10) . . . . ?
C7 N2 S1 O1 -167.73(9) . . . . ?
C7 N2 S1 C1 -51.43(10) . . . . ?
C6 C1 S1 O2 -10.68(11) . . . . ?
C2 C1 S1 O2 168.93(8) . . . . ?
C6 C1 S1 O1 -140.77(9) . . . . ?
C2 C1 S1 O1 38.84(10) . . . . ?
C6 C1 S1 N2 106.50(10) . . . . ?
C2 C1 S1 N2 -73.90(10) . . . . ?
