#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013833.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_2013833
loop_
_publ_author_name
'Nagarajan Vembu'
'Maruthai Nallu'
'Semih Durmus'
'Mathew Pazner'
'Jered Garrison'
'Wiley J. Youngs'
_publ_section_title
;
 2-Chlorophenyl 3-nitrobenzenesulfonate and 2,4-dichlorophenyl
 3-nitrobenzenesulfonate: supramolecular aggregation through
 C--H···O, π--π and van der Waals interactions
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o65
_journal_page_last               o68
_journal_paper_doi               10.1107/S0108270103027380
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C12 H7 Cl2 N O5 S'
_chemical_formula_moiety         'C12 H7 Cl2 N O5 S'
_chemical_formula_sum            'C12 H7 Cl2 N O5 S'
_chemical_formula_weight         348.15
_chemical_melting_point          366.5(5)
_chemical_name_systematic
;
  2,4-Dichlorophenyl 3-nitrobenzenesulfonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.878(5)
_cell_length_b                   13.330(10)
_cell_length_c                   14.990(11)
_cell_measurement_reflns_used    7544
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.72
_cell_volume                     1374.3(18)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11316
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.8303
_exptl_absorpt_correction_T_min  0.7390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.283
_refine_ls_abs_structure_details 'Flack (1983), 1283 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                3158
_reflns_number_total             3268
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1154.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '366-367' was changed to '366.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '366-367' was changed to '366.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1374.3(17)
_cod_database_code               2013833
_cod_database_fobs_code          2013833
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'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.37528(8) 0.72585(4) 1.16297(4) 0.03515(14) Uani d . 1 . . Cl
Cl2 0.70015(8) 0.36113(4) 1.12658(4) 0.03054(13) Uani d . 1 . . Cl
S1 1.11206(7) 0.46106(4) 0.96706(3) 0.02198(12) Uani d . 1 . . S
N1 0.4809(3) 0.53990(16) 0.79536(12) 0.0313(4) Uani d . 1 . . N
O1 0.3376(3) 0.51043(15) 0.75540(11) 0.0438(5) Uani d . 1 . . O
O2 0.5212(3) 0.62900(13) 0.80680(12) 0.0405(4) Uani d . 1 . . O
O3 1.1685(2) 0.55771(11) 0.93622(10) 0.0288(3) Uani d . 1 . . O
O4 1.2483(2) 0.38069(11) 0.97053(11) 0.0312(3) Uani d . 1 . . O
O5 1.0425(2) 0.47127(10) 1.06854(9) 0.0226(3) Uani d . 1 . . O
C1 0.8539(3) 0.32184(16) 0.90651(14) 0.0268(4) Uani d . 1 . . C
C2 0.9000(3) 0.42355(14) 0.91084(12) 0.0215(4) Uani d . 1 . . C
C3 0.7817(3) 0.49665(14) 0.87385(13) 0.0224(4) Uani d . 1 . . C
C4 0.6136(3) 0.46416(16) 0.83191(13) 0.0247(4) Uani d . 1 . . C
C5 0.5673(4) 0.36347(18) 0.82348(14) 0.0299(5) Uani d . 1 . . C
C6 0.6883(4) 0.29243(16) 0.86107(15) 0.0313(5) Uani d . 1 . . C
C7 0.8835(3) 0.53413(14) 1.08739(12) 0.0197(4) Uani d . 1 . . C
C8 0.8992(3) 0.63802(15) 1.08168(14) 0.0241(4) Uani d . 1 . . C
C9 0.7417(3) 0.69705(15) 1.10415(15) 0.0258(4) Uani d . 1 . . C
C10 0.5719(3) 0.65118(15) 1.13297(14) 0.0245(4) Uani d . 1 . . C
C11 0.5549(3) 0.54799(15) 1.13981(13) 0.0236(4) Uani d . 1 . . C
C12 0.7131(3) 0.48969(13) 1.11678(13) 0.0205(4) Uani d . 1 . . C
H1 0.935(4) 0.2748(18) 0.9338(16) 0.025(6) Uiso d . 1 . . H
H3 0.813(4) 0.5681(18) 0.8779(15) 0.029(6) Uiso d . 1 . . H
H5 0.470(4) 0.3520(19) 0.7947(16) 0.028(7) Uiso d . 1 . . H
H6 0.656(4) 0.225(2) 0.8561(17) 0.042(8) Uiso d . 1 . . H
H8 0.999(4) 0.6661(17) 1.0625(15) 0.022(6) Uiso d . 1 . . H
H9 0.755(4) 0.7601(19) 1.1020(15) 0.026(6) Uiso d . 1 . . H
H11 0.447(4) 0.526(2) 1.1590(16) 0.031(7) Uiso d . 1 . . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
O3 S1 O4 120.90(10) y
O3 S1 O5 108.26(9) y
O4 S1 O5 103.06(9) y
O3 S1 C2 109.18(10) y
O4 S1 C2 110.45(10) y
O5 S1 C2 103.41(9) y
O1 N1 O2 124.1(2) y
O1 N1 C4 117.7(2) y
O2 N1 C4 118.16(19) y
C7 O5 S1 118.30(12) y
C6 C1 C2 119.1(2) ?
C6 C1 H1 121.2(16) ?
C2 C1 H1 119.7(16) ?
C3 C2 C1 122.1(2) ?
C3 C2 S1 118.65(16) ?
C1 C2 S1 119.22(16) ?
C4 C3 C2 116.87(18) ?
C4 C3 H3 121.1(15) ?
C2 C3 H3 122.0(15) ?
C3 C4 C5 122.4(2) ?
C3 C4 N1 118.3(2) ?
C5 C4 N1 119.3(2) ?
C6 C5 C4 119.2(2) ?
C6 C5 H5 125.8(18) ?
C4 C5 H5 114.9(18) ?
C5 C6 C1 120.2(2) ?
C5 C6 H6 119.2(18) ?
C1 C6 H6 120.6(18) ?
C12 C7 C8 120.72(18) ?
C12 C7 O5 117.84(17) ?
C8 C7 O5 121.34(18) ?
C9 C8 C7 119.4(2) ?
C9 C8 H8 118.4(16) ?
C7 C8 H8 122.1(16) ?
C8 C9 C10 119.03(19) ?
C8 C9 H9 118.3(18) ?
C10 C9 H9 122.6(18) ?
C11 C10 C9 122.17(19) ?
C11 C10 Cl1 118.93(17) ?
C9 C10 Cl1 118.89(16) ?
C12 C11 C10 118.28(19) ?
C12 C11 H11 125.5(18) ?
C10 C11 H11 116.2(18) ?
C11 C12 C7 120.37(18) ?
C11 C12 Cl2 119.85(16) ?
C7 C12 Cl2 119.77(15) ?
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 C10 . 1.739(2) y
Cl2 C12 . 1.722(2) y
S1 O3 . 1.4229(17) y
S1 O4 . 1.4240(16) y
S1 O5 . 1.6006(18) y
S1 C2 . 1.757(2) y
N1 O1 . 1.219(3) y
N1 O2 . 1.232(3) y
N1 C4 . 1.467(3) y
O5 C7 . 1.406(2) y
C1 C6 . 1.384(3) ?
C1 C2 . 1.394(3) ?
C1 H1 . 0.94(3) ?
C2 C3 . 1.386(3) ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.98(2) ?
C4 C5 . 1.385(3) ?
C5 C6 . 1.381(4) ?
C5 H5 . 0.81(3) ?
C6 H6 . 0.93(3) ?
C7 C12 . 1.385(3) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.84(3) ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.85(2) ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.85(3) ?
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
C1 H1 O4 . 0.94(3) 2.63(3) 2.982(3) 102.8(17) y
C3 H3 O2 . 0.98(2) 2.41(2) 2.708(3) 96.7(17) y
C3 H3 O3 . 0.98(2) 2.60(3) 2.935(3) 100.2(17) y
C5 H5 O1 . 0.81(3) 2.37(3) 2.716(3) 106(2) y
C8 H8 O3 . 0.84(3) 2.65(2) 3.055(3) 111.3(18) y
C6 H6 O5 4_457 0.93(3) 2.95(3) 3.805(3) 153(2) y
C1 H1 O4 4_457 0.94(3) 2.83(2) 3.349(3) 116.1(19) y
C9 H9 O2 4_567 0.85(2) 2.72(2) 3.294(3) 126(2) y
C9 H9 O3 4_467 0.85(2) 2.56(3) 3.362(3) 158(2) y
C11 H11 O1 2_565 0.85(3) 2.48(3) 3.301(3) 163(2) y
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
O3 S1 O5 C7 60.59(16) ?
O4 S1 O5 C7 -170.24(14) ?
C2 S1 O5 C7 -55.15(16) y
C6 C1 C2 C3 2.4(3) ?
C6 C1 C2 S1 -179.05(16) ?
O3 S1 C2 C3 -22.82(18) ?
O4 S1 C2 C3 -158.06(15) ?
O5 S1 C2 C3 92.26(16) ?
O3 S1 C2 C1 158.59(16) ?
O4 S1 C2 C1 23.35(19) ?
O5 S1 C2 C1 -86.33(17) ?
C1 C2 C3 C4 0.0(3) ?
S1 C2 C3 C4 -178.54(14) ?
C2 C3 C4 C5 -2.5(3) ?
C2 C3 C4 N1 177.46(17) ?
O1 N1 C4 C3 177.05(19) ?
O2 N1 C4 C3 -2.9(3) ?
O1 N1 C4 C5 -3.0(3) ?
O2 N1 C4 C5 177.12(19) ?
C3 C4 C5 C6 2.6(3) ?
N1 C4 C5 C6 -177.40(19) ?
C4 C5 C6 C1 -0.1(3) ?
C2 C1 C6 C5 -2.4(3) ?
S1 O5 C7 C12 112.47(17) ?
S1 O5 C7 C8 -71.1(2) ?
C12 C7 C8 C9 -1.1(3) ?
O5 C7 C8 C9 -177.47(18) ?
C7 C8 C9 C10 0.8(3) ?
C8 C9 C10 C11 -0.1(3) ?
C8 C9 C10 Cl1 178.94(16) ?
C9 C10 C11 C12 -0.1(3) ?
Cl1 C10 C11 C12 -179.22(15) ?
C10 C11 C12 C7 -0.2(3) ?
C10 C11 C12 Cl2 178.58(16) ?
C8 C7 C12 C11 0.9(3) ?
O5 C7 C12 C11 177.33(17) ?
C8 C7 C12 Cl2 -177.94(15) ?
O5 C7 C12 Cl2 -1.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134352
