#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519278.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_1519278
loop_
_publ_author_name
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Mayer, Thomas A.'
'Threlfall, Terry L.'
_publ_section_title
;
 4-Amino-N-(4-methyl-1H-pyridin-2-ylidene)-benzenesulfonamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              180
_journal_year                    2000
_chemical_formula_sum            'C12 H13 N3 O2 S'
_chemical_formula_weight         263.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.837(3)
_cell_length_b                   8.6247(17)
_cell_length_c                   18.643(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.94
_cell_volume                     2539.8(9)
_computing_cell_refinement       'DENZO & COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9299
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                1731
_reflns_number_total             2899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-180.cif
_cod_data_source_block           00tam008
_cod_depositor_comments
;
Citation :
Coles, Simon J. and Hursthouse, Michael B. and Mayer, Thomas A. and 
Threlfall, Terry L (2000) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/180)

More at:
http://ecrystals.chem.soton.ac.uk/180/
;
_cod_original_cell_volume        2539.9(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1519278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H13 H 0.7603(17) -0.162(3) 0.3191(15) 0.068(7) Uiso 1 1 d . . .
H18 H 0.6500(16) -0.622(3) 0.4806(14) 0.067(8) Uiso 1 1 d . . .
H19 H 0.5202(16) -0.642(3) 0.4110(13) 0.060(7) Uiso 1 1 d . . .
H21 H 0.5320(14) -0.191(3) 0.3636(12) 0.053(7) Uiso 1 1 d . . .
H17 H 0.7074(15) -0.390(2) 0.4920(13) 0.043(7) Uiso 1 1 d . . .
H16 H 0.5770(16) 0.105(3) 0.1611(15) 0.059(7) Uiso 1 1 d . . .
H15 H 0.5719(17) 0.142(3) 0.2874(14) 0.067(8) Uiso 1 1 d . . .
H12 H 0.7626(17) -0.193(3) 0.1917(15) 0.074(8) Uiso 1 1 d . . .
H22C H 0.4205(18) -0.354(3) 0.2998(16) 0.076(9) Uiso 1 1 d . . .
H22A H 0.427(2) -0.535(4) 0.3118(19) 0.097(10) Uiso 1 1 d . . .
H10 H 0.629(2) -0.017(3) 0.0646(18) 0.083(10) Uiso 1 1 d . . .
H11 H 0.692(2) -0.155(4) 0.077(2) 0.112(14) Uiso 1 1 d . . .
H22B H 0.390(3) -0.436(4) 0.360(2) 0.124(17) Uiso 1 1 d . . .
S11 S 0.66000(4) 0.01980(6) 0.40594(3) 0.0435(2) Uani 1 1 d . . .
O11 O 0.72842(11) 0.12144(16) 0.43097(9) 0.0555(5) Uani 1 1 d . . .
O12 O 0.57637(10) 0.07475(17) 0.41860(9) 0.0536(5) Uani 1 1 d . . .
N13 N 0.66034(14) -0.3979(2) 0.46439(11) 0.0480(5) Uani 1 1 d . . .
N12 N 0.68261(12) -0.14296(18) 0.44271(10) 0.0457(5) Uani 1 1 d . . .
C14 C 0.66340(14) -0.0059(2) 0.31295(12) 0.0391(5) Uani 1 1 d . . .
C17 C 0.63132(14) -0.2671(2) 0.43052(12) 0.0418(6) Uani 1 1 d . . .
C13 C 0.72105(16) -0.1073(3) 0.28535(14) 0.0500(6) Uani 1 1 d . . .
C15 C 0.60957(16) 0.0756(3) 0.26554(13) 0.0489(6) Uani 1 1 d . . .
C18 C 0.62096(17) -0.5359(3) 0.45658(16) 0.0580(7) Uani 1 1 d . . .
C11 C 0.66636(16) -0.0490(3) 0.16486(13) 0.0493(6) Uani 1 1 d . . .
C21 C 0.55507(15) -0.2811(3) 0.38772(14) 0.0493(6) Uani 1 1 d . . .
C12 C 0.72290(18) -0.1277(3) 0.21258(15) 0.0564(7) Uani 1 1 d . . .
C19 C 0.54869(18) -0.5500(3) 0.41443(16) 0.0587(7) Uani 1 1 d . . .
C20 C 0.51386(15) -0.4207(3) 0.37851(14) 0.0526(6) Uani 1 1 d . . .
C16 C 0.61082(18) 0.0546(3) 0.19282(15) 0.0569(7) Uani 1 1 d . . .
N11 N 0.6653(2) -0.0777(4) 0.09228(14) 0.0784(8) Uani 1 1 d . . .
C22 C 0.4332(2) -0.4339(4) 0.3324(3) 0.0758(10) Uani 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 0.0000 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'
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
O12 S11 O11 115.08(10) . .
O12 S11 N12 113.58(10) . .
O11 S11 N12 104.82(10) . .
O12 S11 C14 107.32(11) . .
O11 S11 C14 108.69(11) . .
N12 S11 C14 107.01(10) . .
C18 N13 C17 123.1(2) . .
C17 N12 S11 120.79(15) . .
C15 C14 C13 118.5(2) . .
C15 C14 S11 120.60(18) . .
C13 C14 S11 120.91(18) . .
N12 C17 N13 113.6(2) . .
N12 C17 C21 130.16(19) . .
N13 C17 C21 116.2(2) . .
C12 C13 C14 120.6(2) . .
C16 C15 C14 121.0(2) . .
C19 C18 N13 120.7(2) . .
N11 C11 C16 121.7(3) . .
N11 C11 C12 120.2(3) . .
C16 C11 C12 118.1(2) . .
C20 C21 C17 121.9(2) . .
C13 C12 C11 120.8(2) . .
C18 C19 C20 119.9(2) . .
C21 C20 C19 118.2(2) . .
C21 C20 C22 121.2(2) . .
C19 C20 C22 120.5(2) . .
C15 C16 C11 120.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S11 O12 1.4421(17) .
S11 O11 1.4447(16) .
S11 N12 1.5916(17) .
S11 C14 1.752(2) .
N13 C18 1.346(3) .
N13 C17 1.357(3) .
N12 C17 1.353(3) .
C14 C15 1.376(3) .
C14 C13 1.390(3) .
C17 C21 1.404(3) .
C13 C12 1.371(4) .
C15 C16 1.369(4) .
C18 C19 1.346(4) .
C11 N11 1.374(3) .
C11 C16 1.382(3) .
C11 C12 1.392(4) .
C21 C20 1.374(3) .
C19 C20 1.394(3) .
C20 C22 1.492(4) .
