#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209353.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_2209353
loop_
_publ_author_name
'Silva, Luiz Everson da'
'Andrighetti-Fröhner, Carla Regina'
'Nunes, Ricardo José'
'Simões, Cláudia Maria Oliviera'
'Foro, Sabine'
_publ_section_title
;
 Quinolin-8-yl 2,5-dichlorobenzenesulfonate
;
_journal_coeditor_code           XU2030
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2104
_journal_page_last               o2105
_journal_paper_doi               10.1107/S1600536806015017
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H9 Cl2 N O3 S'
_chemical_formula_moiety         'C15 H9 Cl2 N O3 S'
_chemical_formula_sum            'C15 H9 Cl2 N O3 S'
_chemical_formula_weight         354.19
_chemical_name_systematic
;
Quinolin-8-yl 2,5-dichlorobenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8420(10)
_cell_length_b                   25.536(3)
_cell_length_c                   7.6420(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.2
_cell_measurement_theta_min      7.9
_cell_volume                     1456.5(3)
_computing_cell_refinement       CAD-4-PC
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1993)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3088
_diffrn_reflns_theta_full        67.0
_diffrn_reflns_theta_max         67.0
_diffrn_reflns_theta_min         3.5
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.462
_exptl_absorpt_correction_T_max  0.285
_exptl_absorpt_correction_T_min  0.129
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.60
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0696P)²+0.9445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.127
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                2301
_reflns_number_total             2593
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209353
_cod_database_fobs_code          2209353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
C C1 0.1042(4) 0.30270(10) 0.4318(4) 0.0450(6) Uani d . 1
C C2 0.1871(4) 0.25658(13) 0.4976(4) 0.0564(7) Uani d . 1
H H2 0.2967 0.2566 0.5901 0.068 Uiso calc R 1
C C3 0.1059(5) 0.20896(12) 0.4244(5) 0.0608(8) Uani d . 1
H H3 0.1635 0.1775 0.4672 0.073 Uiso calc R 1
C C4 -0.0550(4) 0.20844(10) 0.2927(4) 0.0533(7) Uani d . 1
H H4 -0.1083 0.1767 0.2471 0.064 Uiso calc R 1
C C5 -0.1421(4) 0.25543(10) 0.2244(4) 0.0441(6) Uani d . 1
C C6 -0.3117(4) 0.25745(13) 0.0862(4) 0.0576(7) Uani d . 1
H H6 -0.3689 0.2267 0.0344 0.069 Uiso calc R 1
C C7 -0.3889(4) 0.30431(14) 0.0308(5) 0.0656(8) Uani d . 1
H H7 -0.4985 0.3063 -0.0612 0.079 Uiso calc R 1
C C8 -0.3022(4) 0.34978(13) 0.1134(5) 0.0645(8) Uani d . 1
H H8 -0.3604 0.3815 0.0764 0.077 Uiso calc R 1
C C9 -0.0646(3) 0.30415(9) 0.2955(4) 0.0406(5) Uani d . 1
C C10 0.2789(3) 0.44366(10) 0.4768(4) 0.0465(6) Uani d . 1
C C11 0.2358(4) 0.47269(11) 0.3165(4) 0.0502(6) Uani d . 1
H H11 0.2361 0.4571 0.2067 0.060 Uiso calc R 1
C C12 0.1922(4) 0.52498(12) 0.3202(4) 0.0541(7) Uani d . 1
C C13 0.1907(4) 0.54871(12) 0.4806(5) 0.0595(8) Uani d . 1
H H13 0.1613 0.5840 0.4816 0.071 Uiso calc R 1
C C14 0.2332(4) 0.51973(12) 0.6404(5) 0.0592(8) Uani d . 1
H H14 0.2317 0.5356 0.7494 0.071 Uiso calc R 1
C C15 0.2782(4) 0.46717(11) 0.6409(4) 0.0496(6) Uani d . 1
N N1 -0.1448(3) 0.35120(9) 0.2392(4) 0.0544(6) Uani d . 1
O O1 0.1756(3) 0.35076(8) 0.5139(3) 0.0603(6) Uani d . 1
O O2 0.3192(3) 0.36556(9) 0.2750(3) 0.0655(6) Uani d . 1
O O3 0.4985(3) 0.36521(9) 0.5983(4) 0.0696(7) Uani d . 1
Cl Cl1 0.13767(13) 0.56101(3) 0.11801(13) 0.0760(3) Uani d . 1
Cl Cl2 0.32532(13) 0.43289(4) 0.84547(11) 0.0727(3) Uani d . 1
S S1 0.33500(8) 0.37715(3) 0.46059(10) 0.0478(2) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 C9 121.8(3)
C2 C1 O1 120.5(3)
C9 C1 O1 117.3(2)
C1 C2 C3 119.5(3)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 120.7(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.4(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C9 120.4(3)
C4 C5 C6 123.1(3)
C9 C5 C6 116.5(2)
C7 C6 C5 119.5(3)
C7 C6 H6 120.3
C5 C6 H6 120.3
C6 C7 C8 119.2(3)
C6 C7 H7 120.4
C8 C7 H7 120.4
N1 C8 C7 124.9(3)
N1 C8 H8 117.5
C7 C8 H8 117.5
N1 C9 C1 119.6(2)
N1 C9 C5 123.4(2)
C1 C9 C5 117.0(2)
C11 C10 C15 120.0(3)
C11 C10 S1 116.9(2)
C15 C10 S1 123.2(2)
C12 C11 C10 119.7(3)
C12 C11 H11 120.2
C10 C11 H11 120.2
C13 C12 C11 121.1(3)
C13 C12 Cl1 119.7(2)
C11 C12 Cl1 119.3(2)
C12 C13 C14 119.3(3)
C12 C13 H13 120.4
C14 C13 H13 120.4
C13 C14 C15 120.9(3)
C13 C14 H14 119.5
C15 C14 H14 119.5
C14 C15 C10 119.1(3)
C14 C15 Cl2 118.4(2)
C10 C15 Cl2 122.5(2)
C8 N1 C9 116.5(3)
C1 O1 S1 119.54(17)
O2 S1 O3 118.61(15)
O2 S1 O1 109.65(13)
O3 S1 O1 108.86(14)
O2 S1 C10 108.88(14)
O3 S1 C10 109.98(13)
O1 S1 C10 99.10(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.365(4)
C1 C9 1.412(4)
C1 O1 1.413(3)
C2 C3 1.406(5)
C2 H2 0.9300
C3 C4 1.352(5)
C3 H3 0.9300
C4 C5 1.400(4)
C4 H4 0.9300
C5 C9 1.418(4)
C5 C6 1.423(4)
C6 C7 1.349(5)
C6 H6 0.9300
C7 C8 1.395(5)
C7 H7 0.9300
C8 N1 1.312(4)
C8 H8 0.9300
C9 N1 1.363(3)
C10 C11 1.382(4)
C10 C15 1.392(4)
C10 S1 1.768(3)
C11 C12 1.381(4)
C11 H11 0.9300
C12 C13 1.370(4)
C12 Cl1 1.735(3)
C13 C14 1.378(5)
C13 H13 0.9300
C14 C15 1.388(4)
C14 H14 0.9300
C15 Cl2 1.730(3)
O1 S1 1.580(2)
O2 S1 1.416(2)
O3 S1 1.420(2)
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
C3 H3 O2 4_566 0.93 2.54 3.294(4) 138
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
C9 C1 C2 C3 1.9(4)
O1 C1 C2 C3 174.6(3)
C1 C2 C3 C4 -1.4(5)
C2 C3 C4 C5 1.2(4)
C3 C4 C5 C9 -1.5(4)
C3 C4 C5 C6 -179.8(3)
C4 C5 C6 C7 178.4(3)
C9 C5 C6 C7 -0.1(4)
C5 C6 C7 C8 -1.4(5)
C6 C7 C8 N1 2.6(5)
C2 C1 C9 N1 177.6(3)
O1 C1 C9 N1 4.8(4)
C2 C1 C9 C5 -2.2(4)
O1 C1 C9 C5 -175.0(2)
C4 C5 C9 N1 -177.9(3)
C6 C5 C9 N1 0.6(4)
C4 C5 C9 C1 1.9(4)
C6 C5 C9 C1 -179.6(2)
C15 C10 C11 C12 0.0(4)
S1 C10 C11 C12 -179.5(2)
C10 C11 C12 C13 -0.1(4)
C10 C11 C12 Cl1 -179.8(2)
C11 C12 C13 C14 -0.1(4)
Cl1 C12 C13 C14 179.7(2)
C12 C13 C14 C15 0.3(5)
C13 C14 C15 C10 -0.4(4)
C13 C14 C15 Cl2 -178.6(2)
C11 C10 C15 C14 0.2(4)
S1 C10 C15 C14 179.7(2)
C11 C10 C15 Cl2 178.4(2)
S1 C10 C15 Cl2 -2.2(3)
C7 C8 N1 C9 -2.0(5)
C1 C9 N1 C8 -179.4(3)
C5 C9 N1 C8 0.4(4)
C2 C1 O1 S1 81.4(3)
C9 C1 O1 S1 -105.7(2)
C1 O1 S1 O2 32.3(3)
C1 O1 S1 O3 -98.9(2)
C1 O1 S1 C10 146.2(2)
C11 C10 S1 O2 -1.6(2)
C15 C10 S1 O2 178.9(2)
C11 C10 S1 O3 129.9(2)
C15 C10 S1 O3 -49.6(3)
C11 C10 S1 O1 -116.1(2)
C15 C10 S1 O1 64.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1484261
