#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238942.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_2238942
loop_
_publ_author_name
'Suchetan, Parameshwar Adimoole'
'Mohan, Revanasiddappa Nadigar'
Vijithkumar
'Palakshamurthy, Bandrehalli Siddagangaiah'
'Sreenivasa, Swamy'
_publ_section_title
;
 6-Chloro-N-(pyridin-4-ylmethyl)pyridine-3-sulfonamide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1765
_journal_paper_doi               10.1107/S1600536813030523
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H10 Cl N3 O2 S'
_chemical_formula_moiety         'C11 H10 Cl N3 O2 S'
_chemical_formula_sum            'C11 H10 Cl N3 O2 S'
_chemical_formula_weight         283.73
_chemical_melting_point          492
_chemical_name_systematic
;
6-Chloro-N-(pyridin-4-ylmethyl)pyridine-3-sulfonamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.388(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4140(6)
_cell_length_b                   18.172(2)
_cell_length_c                   12.9392(15)
_cell_measurement_reflns_used    1103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.9
_cell_volume                     1271.9(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20929
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.387
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.824
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0442
_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)+(0.0847P)²+0.7427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                2185
_reflns_number_total             2961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2782.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238942
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
_atom_site_symmetry_multiplicity
H HN2 0.486(4) 0.3469(13) 0.213(2) 0.058(7) Uiso d . 1 1
S S1 0.32655(10) 0.44681(3) 0.19440(4) 0.0590(2) Uani d . 1 1
Cl Cl1 1.10225(15) 0.64661(4) 0.41805(6) 0.0911(3) Uani d . 1 1
C C1 0.5418(4) 0.50525(11) 0.25986(16) 0.0486(4) Uani d . 1 1
C C7 0.6225(4) 0.32076(10) 0.00501(15) 0.0474(4) Uani d . 1 1
N N2 0.4712(4) 0.37356(11) 0.16614(15) 0.0584(5) Uani d . 1 1
C C3 0.8769(4) 0.59143(12) 0.35659(18) 0.0600(5) Uani d . 1 1
N N3 0.5621(4) 0.22140(11) -0.15918(16) 0.0692(5) Uani d . 1 1
C C11 0.4300(4) 0.27124(12) -0.00074(17) 0.0571(5) Uani d . 1 1
H H11 0.3157 0.2700 0.0509 0.068 Uiso calc R 1 1
N N1 0.8263(5) 0.60509(13) 0.2581(2) 0.0899(7) Uani d . 1 1
O O1 0.1498(3) 0.42543(11) 0.26714(16) 0.0804(5) Uani d . 1 1
O O2 0.2501(4) 0.48324(12) 0.10098(16) 0.0912(6) Uani d . 1 1
C C10 0.4071(4) 0.22353(13) -0.08329(19) 0.0653(6) Uani d . 1 1
H H10 0.2746 0.1909 -0.0856 0.078 Uiso calc R 1 1
C C5 0.6049(6) 0.49344(15) 0.36172(19) 0.0785(8) Uani d . 1 1
H H5 0.5314 0.4553 0.3973 0.094 Uiso calc R 1 1
C C2 0.6559(6) 0.56102(15) 0.2099(2) 0.0822(8) Uani d . 1 1
H H2 0.6153 0.5691 0.1402 0.099 Uiso calc R 1 1
C C8 0.7862(5) 0.31869(14) -0.0734(2) 0.0676(6) Uani d . 1 1
H H8 0.9200 0.3508 -0.0731 0.081 Uiso calc R 1 1
C C6 0.6641(4) 0.37509(14) 0.09095(17) 0.0635(6) Uani d . 1 1
H H6A 0.8220 0.3648 0.1262 0.076 Uiso calc R 1 1
H H6B 0.6725 0.4241 0.0617 0.076 Uiso calc R 1 1
C C4 0.7741(6) 0.53707(15) 0.41083(18) 0.0797(8) Uani d . 1 1
H H4 0.8183 0.5298 0.4803 0.096 Uiso calc R 1 1
C C9 0.7497(5) 0.26847(16) -0.1525(2) 0.0805(8) Uani d . 1 1
H H9 0.8635 0.2675 -0.2044 0.097 Uiso calc R 1 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 120.54(13)
O1 S1 N2 105.88(11)
O2 S1 N2 108.75(13)
O1 S1 C1 107.16(11)
O2 S1 C1 106.87(11)
N2 S1 C1 106.94(10)
C2 C1 C5 118.3(2)
C2 C1 S1 121.47(18)
C5 C1 S1 120.14(17)
C11 C7 C8 116.9(2)
C11 C7 C6 124.15(19)
C8 C7 C6 118.97(19)
C6 N2 S1 120.65(17)
C6 N2 HN2 118.6(19)
S1 N2 HN2 112.0(18)
N1 C3 C4 124.7(2)
N1 C3 Cl1 116.52(19)
C4 C3 Cl1 118.74(19)
C10 N3 C9 116.2(2)
C7 C11 C10 119.8(2)
C7 C11 H11 120.1
C10 C11 H11 120.1
C3 N1 C2 116.4(2)
N3 C10 C11 123.8(2)
N3 C10 H10 118.1
C11 C10 H10 118.1
C4 C5 C1 120.0(2)
C4 C5 H5 120.0
C1 C5 H5 120.0
N1 C2 C1 122.3(2)
N1 C2 H2 118.9
C1 C2 H2 118.9
C7 C8 C9 119.2(2)
C7 C8 H8 120.4
C9 C8 H8 120.4
N2 C6 C7 113.18(17)
N2 C6 H6A 108.9
C7 C6 H6A 108.9
N2 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.8
C3 C4 C5 118.2(2)
C3 C4 H4 120.9
C5 C4 H4 120.9
N3 C9 C8 124.1(2)
N3 C9 H9 118.0
C8 C9 H9 118.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4238(19)
S1 O2 1.4244(18)
S1 N2 1.595(2)
S1 C1 1.767(2)
Cl1 C3 1.745(2)
C1 C2 1.364(3)
C1 C5 1.365(3)
C7 C11 1.376(3)
C7 C8 1.375(3)
C7 C6 1.497(3)
N2 C6 1.457(3)
N2 HN2 0.78(3)
C3 N1 1.316(3)
C3 C4 1.346(3)
N3 C10 1.318(3)
N3 C9 1.328(3)
C11 C10 1.377(3)
C11 H11 0.9300
N1 C2 1.354(3)
C10 H10 0.9300
C5 C4 1.350(3)
C5 H5 0.9300
C2 H2 0.9300
C8 C9 1.379(4)
C8 H8 0.9300
C6 H6A 0.9700
C6 H6B 0.9700
C4 H4 0.9300
C9 H9 0.9300
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
N2 HN2 N3 4_566 0.78(3) 2.10(3) 2.870(3) 174.53
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
O1 S1 C1 C2 -148.2(2)
O2 S1 C1 C2 -17.7(3)
N2 S1 C1 C2 98.7(2)
O1 S1 C1 C5 34.4(2)
O2 S1 C1 C5 164.9(2)
N2 S1 C1 C5 -78.7(2)
O1 S1 N2 C6 178.59(17)
O2 S1 N2 C6 47.7(2)
C1 S1 N2 C6 -67.37(19)
C8 C7 C11 C10 -0.9(3)
C6 C7 C11 C10 179.8(2)
C4 C3 N1 C2 0.7(5)
Cl1 C3 N1 C2 178.4(2)
C9 N3 C10 C11 0.5(4)
C7 C11 C10 N3 0.5(4)
C2 C1 C5 C4 0.9(4)
S1 C1 C5 C4 178.3(2)
C3 N1 C2 C1 0.0(5)
C5 C1 C2 N1 -0.7(5)
S1 C1 C2 N1 -178.2(2)
C11 C7 C8 C9 0.3(3)
C6 C7 C8 C9 179.6(2)
S1 N2 C6 C7 -125.57(19)
C11 C7 C6 N2 -3.3(3)
C8 C7 C6 N2 177.4(2)
N1 C3 C4 C5 -0.6(5)
Cl1 C3 C4 C5 -178.2(2)
C1 C5 C4 C3 -0.2(5)
C10 N3 C9 C8 -1.2(4)
C7 C8 C9 N3 0.8(4)
