#------------------------------------------------------------------------------
#$Date: 2015-08-28 05:00:20 +0300 (Fri, 28 Aug 2015) $
#$Revision: 153743 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/00/2020096.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_2020096
loop_
_publ_author_name
'Köktaş Koca, Serap'
'Sevinçek, Resul'
'Akgül, Özlem'
'Aygün, Muhittin'
_publ_section_title
;
 Positional isomeric effect on the crystallization of chlorine-substituted
 N-phenyl-2-phthalimidoethanesulfonamide derivatives
;
_journal_coeditor_code           WQ3094
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              839
_journal_page_last               843
_journal_paper_doi               10.1107/S2053229615015223
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H13 Cl N2 O4 S'
_chemical_formula_moiety         'C16 H13 Cl N2 O4 S'
_chemical_formula_sum            'C16 H13 Cl N2 O4 S'
_chemical_formula_weight         364.79
_chemical_name_systematic
;
N-(2-chlorophenyl)-2-phthalimidoethanesulfonamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4126(2)
_cell_length_b                   12.7656(5)
_cell_length_c                   22.6827(8)
_cell_measurement_reflns_used    1162
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3170
_cell_measurement_theta_min      3.9200
_cell_volume                     1567.26(10)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2014)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4676
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.192
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3478
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.0474
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.294
_refine_ls_abs_structure_details
;
Flack x parameter determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0368
_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)+(0.0353P)²+0.1242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                2484
_reflns_number_total             2894
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wq3094sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1567.26(11)
_cod_database_code               2020096
_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.
;
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_occupancy
Cl Cl1 0.1528(2) 0.56965(9) 0.18287(5) 0.0680(4) Uani d 1
S S1 0.55647(15) 0.26803(7) 0.19537(4) 0.0370(2) Uani d 1
O O1 0.5602(5) 0.1892(2) 0.15096(11) 0.0553(7) Uani d 1
O O2 0.7807(4) 0.2950(2) 0.22485(11) 0.0506(7) Uani d 1
O O3 0.4455(5) 0.2256(2) 0.40447(10) 0.0553(7) Uani d 1
O O4 0.5984(6) 0.49229(19) 0.27603(11) 0.0546(8) Uani d 1
N N1 0.4553(6) 0.3769(2) 0.16682(13) 0.0393(7) Uani d 1
N N2 0.4780(5) 0.3494(2) 0.33100(11) 0.0339(6) Uani d 1
C C1 0.1054(7) 0.4755(3) 0.12845(15) 0.0407(8) Uani d 1
C C2 -0.0807(8) 0.4903(4) 0.0879(2) 0.0573(11) Uani d 1
C C3 -0.1259(9) 0.4152(4) 0.0464(2) 0.0661(14) Uani d 1
C C4 0.0144(9) 0.3270(4) 0.04528(19) 0.0670(14) Uani d 1
C C5 0.2043(8) 0.3126(4) 0.08425(17) 0.0541(11) Uani d 1
C C6 0.2538(6) 0.3869(3) 0.12702(14) 0.0372(8) Uani d 1
C C7 0.3380(7) 0.2312(3) 0.24945(15) 0.0338(7) Uani d 1
C C8 0.2735(6) 0.3148(3) 0.29420(15) 0.0360(8) Uani d 1
C C9 0.5444(7) 0.3021(3) 0.38401(14) 0.0374(8) Uani d 1
C C10 0.7535(6) 0.3651(3) 0.40753(14) 0.0354(8) Uani d 1
C C11 0.8922(8) 0.3531(3) 0.45783(16) 0.0490(10) Uani d 1
C C12 1.0798(8) 0.4249(4) 0.46783(17) 0.0527(11) Uani d 1
C C13 1.1236(8) 0.5051(4) 0.42894(19) 0.0522(11) Uani d 1
C C14 0.9833(7) 0.5175(3) 0.37819(17) 0.0466(10) Uani d 1
C C15 0.7968(6) 0.4469(3) 0.36876(14) 0.0354(8) Uani d 1
C C16 0.6205(6) 0.4376(3) 0.31878(14) 0.0350(8) Uani d 1
H H8A 0.142(5) 0.290(2) 0.3206(12) 0.024(8) Uiso d 1
H H7A 0.397(6) 0.172(3) 0.2652(14) 0.039(10) Uiso d 1
H H14 1.007(7) 0.574(3) 0.3536(16) 0.054(12) Uiso d 1
H H5 0.301(7) 0.250(3) 0.0823(16) 0.047(11) Uiso d 1
H H1 0.480(6) 0.429(3) 0.1884(14) 0.035(10) Uiso d 1
H H8B 0.206(6) 0.379(3) 0.2774(14) 0.033(9) Uiso d 1
H H3 -0.238(7) 0.428(3) 0.0187(18) 0.062(13) Uiso d 1
H H7B 0.202(6) 0.211(2) 0.2276(14) 0.038(10) Uiso d 1
H H11 0.862(7) 0.295(3) 0.4814(15) 0.046(11) Uiso d 1
H H13 1.238(8) 0.554(3) 0.4382(17) 0.057(12) Uiso d 1
H H2 -0.165(7) 0.546(3) 0.0902(16) 0.044(12) Uiso d 1
H H12 1.174(7) 0.417(3) 0.5054(17) 0.062(12) Uiso d 1
H H4 -0.017(8) 0.275(4) 0.0182(19) 0.074(15) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 1 2 0.1602
-1 -9 -28 0.0353
0 9 28 0.0223
2 1 -31 0.0664
0 -16 16 0.0180
-2 7 28 0.1253
0 15 -17 0.0410
-8 -1 3 0.1815
0 4 -31 0.0232
-3 14 -16 0.0821
0 15 -17 0.0279
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 119.32(15) y
O1 S1 N1 109.09(16) y
O1 S1 C7 108.21(17) y
O2 S1 N1 105.43(16) y
O2 S1 C7 107.94(16) y
N1 S1 C7 106.13(17) y
S1 N1 H1 113(2) ?
C6 N1 S1 125.9(3) ?
C6 N1 H1 115(2) ?
C9 N2 C8 124.1(3) ?
C9 N2 C16 112.3(3) ?
C16 N2 C8 123.5(3) ?
C2 C1 Cl1 119.1(3) ?
C2 C1 C6 121.3(4) ?
C6 C1 Cl1 119.6(3) ?
C1 C2 H2 118(3) ?
C3 C2 C1 119.7(4) ?
C3 C2 H2 123(3) ?
C2 C3 H3 119(3) ?
C4 C3 C2 119.7(4) ?
C4 C3 H3 121(3) ?
C3 C4 C5 121.3(5) ?
C3 C4 H4 120(3) ?
C5 C4 H4 118(3) ?
C4 C5 C6 120.4(4) ?
C4 C5 H5 119(2) ?
C6 C5 H5 120(2) ?
C1 C6 N1 120.1(3) ?
C5 C6 N1 122.2(3) ?
C5 C6 C1 117.6(3) ?
S1 C7 H7A 105(2) ?
S1 C7 H7B 104(2) ?
C8 C7 S1 115.6(3) y
C8 C7 H7A 114(2) ?
C8 C7 H7B 112(2) ?
H7A C7 H7B 105(3) ?
N2 C8 C7 115.0(3) y
N2 C8 H8A 107.5(16) ?
N2 C8 H8B 105.0(19) ?
C7 C8 H8A 110.2(17) ?
C7 C8 H8B 114.5(19) ?
H8A C8 H8B 104(3) ?
O3 C9 N2 124.6(3) ?
O3 C9 C10 129.6(3) ?
N2 C9 C10 105.8(3) ?
C11 C10 C9 130.8(3) ?
C11 C10 C15 121.2(3) ?
C15 C10 C9 108.0(3) ?
C10 C11 C12 117.5(4) ?
C10 C11 H11 118(2) ?
C12 C11 H11 124(2) ?
C11 C12 H12 117(2) ?
C13 C12 C11 120.9(4) ?
C13 C12 H12 122(2) ?
C12 C13 C14 121.6(4) ?
C12 C13 H13 119(3) ?
C14 C13 H13 119(3) ?
C13 C14 H14 121(2) ?
C15 C14 C13 117.2(4) ?
C15 C14 H14 122(2) ?
C10 C15 C16 108.4(3) ?
C14 C15 C10 121.4(3) ?
C14 C15 C16 130.1(3) ?
O4 C16 N2 125.2(3) ?
O4 C16 C15 129.3(3) ?
N2 C16 C15 105.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.742(4) y
S1 O1 1.424(3) y
S1 O2 1.428(3) y
S1 N1 1.629(3) y
S1 C7 1.768(4) y
O3 C9 1.207(4) ?
O4 C16 1.201(4) ?
N1 C6 1.421(4) ?
N1 H1 0.83(3) ?
N2 C8 1.455(4) y
N2 C9 1.392(4) ?
N2 C16 1.393(4) ?
C1 C2 1.378(5) ?
C1 C6 1.388(5) ?
C2 C3 1.365(7) ?
C2 H2 0.85(4) ?
C3 C4 1.359(7) ?
C3 H3 0.89(4) ?
C4 C5 1.368(6) ?
C4 H4 0.92(4) ?
C5 C6 1.383(5) ?
C5 H5 0.96(4) ?
C7 C8 1.514(5) y
C7 H7A 0.90(4) ?
C7 H7B 0.92(3) ?
C8 H8A 0.98(3) ?
C8 H8B 0.97(3) ?
C9 C10 1.487(5) ?
C10 C11 1.374(5) ?
C10 C15 1.385(5) ?
C11 C12 1.386(6) ?
C11 H11 0.93(3) ?
C12 C13 1.372(6) ?
C12 H12 1.00(4) ?
C13 C14 1.388(5) ?
C13 H13 0.90(4) ?
C14 C15 1.370(5) ?
C14 H14 0.93(4) ?
C15 C16 1.487(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
N1 H1 O4 1_555 1_555 1_555 0.84(4) 2.24(3) 2.984(4) 148(3) yes
C5 H5 O1 1_555 1_555 1_555 0.96(4) 2.24(4) 2.912(5) 127(3) yes
C7 H7A O4 1_555 1_555 4_645 0.90(4) 2.48(4) 3.123(5) 129(3) yes
C7 H7B O2 1_555 1_555 1_455 0.92(3) 2.52(3) 3.174(4) 128(2) 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_publ_flag
Cl1 C1 C2 C3 -177.5(4) ?
Cl1 C1 C6 N1 -4.8(4) ?
Cl1 C1 C6 C5 177.9(3) ?
S1 N1 C6 C1 146.9(3) ?
S1 N1 C6 C5 -36.0(5) ?
S1 C7 C8 N2 -62.7(4) y
O1 S1 N1 C6 42.2(3) ?
O1 S1 C7 C8 -169.0(3) ?
O2 S1 N1 C6 171.4(3) ?
O2 S1 C7 C8 60.6(3) ?
O3 C9 C10 C11 1.0(6) ?
O3 C9 C10 C15 -178.6(4) ?
N1 S1 C7 C8 -52.0(3) y
N2 C9 C10 C11 -179.0(4) ?
N2 C9 C10 C15 1.4(3) ?
C1 C2 C3 C4 -0.6(7) ?
C2 C1 C6 N1 175.6(3) ?
C2 C1 C6 C5 -1.6(5) ?
C2 C3 C4 C5 -1.3(7) ?
C3 C4 C5 C6 1.8(7) ?
C4 C5 C6 N1 -177.5(4) ?
C4 C5 C6 C1 -0.3(6) ?
C6 C1 C2 C3 2.1(6) ?
C7 S1 N1 C6 -74.2(3) ?
C8 N2 C9 O3 2.4(5) ?
C8 N2 C9 C10 -177.6(3) ?
C8 N2 C16 O4 -3.1(5) ?
C8 N2 C16 C15 177.0(3) ?
C9 N2 C8 C7 -88.2(4) ?
C9 N2 C16 O4 -179.5(3) ?
C9 N2 C16 C15 0.6(4) ?
C9 C10 C11 C12 179.3(3) ?
C9 C10 C15 C14 -178.7(3) ?
C9 C10 C15 C16 -1.1(4) ?
C10 C11 C12 C13 0.4(6) ?
C10 C15 C16 O4 -179.6(4) ?
C10 C15 C16 N2 0.3(4) ?
C11 C10 C15 C14 1.6(5) ?
C11 C10 C15 C16 179.3(3) ?
C11 C12 C13 C14 -0.2(6) ?
C12 C13 C14 C15 0.7(6) ?
C13 C14 C15 C10 -1.4(6) ?
C13 C14 C15 C16 -178.4(3) ?
C14 C15 C16 O4 -2.2(6) ?
C14 C15 C16 N2 177.7(4) ?
C15 C10 C11 C12 -1.1(5) ?
C16 N2 C8 C7 95.7(4) ?
C16 N2 C9 O3 178.8(3) ?
C16 N2 C9 C10 -1.2(4) ?

_cod_database_fobs_code 2020096
