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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519239.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_1519239
loop_
_publ_author_name
'Threlfall, Terry L.'
'Coles, Simon J.'
'Mayer, Thomas A.'
'Hursthouse, Michael B.'
_publ_section_title
;
 4-Methyl-N-(1H-pyridin-2-ylidene)-benzenesulfonamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              185
_journal_year                    2000
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.728(2)
_cell_length_b                   14.895(3)
_cell_length_c                   14.669(3)
_cell_measurement_temperature    1510(2)
_cell_volume                     2282.1(8)
_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      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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  0.0936
_diffrn_reflns_av_sigmaI/netI    0.1204
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17220
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0020(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   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0547
_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)+(0.0507P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2853
_reflns_number_total             5024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-185.cif
_cod_data_source_block           00tam018
_cod_depositor_comments
;
Citation :
Threlfall, Terry L and Coles, Simon J. and Mayer, Thomas A. and 
Hursthouse, Michael B. (2000) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/185)

More at:
http://ecrystals.chem.soton.ac.uk/185/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1519239
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_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
H21 H 0.747(3) 0.2915(19) 0.786(2) 0.038(8) Uiso 1 1 d . . .
H41 H -0.040(3) 0.2503(16) 0.2290(18) 0.026(7) Uiso 1 1 d . . .
H40 H -0.105(3) 0.3580(18) 0.123(2) 0.031(8) Uiso 1 1 d . . .
H37 H 0.317(3) 0.283(2) 0.195(2) 0.053(10) Uiso 1 1 d . . .
H19 H 0.688(3) 0.4597(19) 0.989(2) 0.031(8) Uiso 1 1 d . . .
H18 H 0.461(3) 0.4342(18) 0.9322(19) 0.033(8) Uiso 1 1 d . . .
H35 H -0.119(3) 0.085(2) 0.210(2) 0.051(10) Uiso 1 1 d . . .
H16 H 0.682(3) 0.431(2) 0.461(2) 0.055(11) Uiso 1 1 d . . .
H38 H 0.258(3) 0.395(2) 0.090(2) 0.055(10) Uiso 1 1 d . . .
H32 H 0.162(3) -0.126(2) 0.131(2) 0.049(10) Uiso 1 1 d . . .
H17 H 0.407(3) 0.3434(17) 0.818(2) 0.021(8) Uiso 1 1 d . . .
H33 H 0.234(3) -0.0258(17) 0.245(2) 0.027(8) Uiso 1 1 d . . .
H20 H 0.832(3) 0.389(2) 0.906(2) 0.055(10) Uiso 1 1 d . . .
H39 H 0.036(3) 0.4386(19) 0.052(2) 0.032(8) Uiso 1 1 d . . .
H13 H 0.348(3) 0.2512(17) 0.4951(18) 0.028(8) Uiso 1 1 d . . .
H15 H 0.721(3) 0.326(2) 0.578(3) 0.057(11) Uiso 1 1 d . . .
H12 H 0.318(3) 0.3606(18) 0.380(2) 0.033(8) Uiso 1 1 d . . .
H36 H -0.196(3) -0.016(2) 0.087(2) 0.053(10) Uiso 1 1 d . . .
H30C H -0.154(5) -0.123(3) -0.024(4) 0.13(2) Uiso 1 1 d . . .
H30A H -0.067(5) -0.205(4) 0.033(4) 0.13(2) Uiso 1 1 d . . .
H30B H -0.029(5) -0.135(3) -0.031(4) 0.110(18) Uiso 1 1 d . . .
S11 S 0.55977(7) 0.20331(5) 0.64132(5) 0.0268(2) Uani 1 1 d . . .
O11 O 0.47913(19) 0.12771(12) 0.60793(13) 0.0329(5) Uani 1 1 d . . .
C20 C 0.7386(3) 0.3780(2) 0.8900(2) 0.0304(7) Uani 1 1 d . . .
O12 O 0.69534(18) 0.18699(13) 0.67255(14) 0.0350(5) Uani 1 1 d . . .
N12 N 0.4957(2) 0.25019(14) 0.71787(16) 0.0268(6) Uani 1 1 d . . .
N13 N 0.4848(2) 0.35026(15) 0.83306(17) 0.0247(6) Uani 1 1 d . . .
C19 C 0.6549(3) 0.42169(19) 0.9361(2) 0.0292(7) Uani 1 1 d . . .
C17 C 0.5617(3) 0.30514(17) 0.78618(19) 0.0236(6) Uani 1 1 d . . .
C18 C 0.5286(3) 0.40627(18) 0.9057(2) 0.0264(7) Uani 1 1 d . . .
C21 C 0.6937(3) 0.32123(19) 0.8170(2) 0.0296(7) Uani 1 1 d . . .
C15 C 0.6399(3) 0.3349(2) 0.5362(2) 0.0350(8) Uani 1 1 d . . .
C14 C 0.5384(3) 0.28166(18) 0.54853(19) 0.0257(7) Uani 1 1 d . . .
C13 C 0.4198(3) 0.2904(2) 0.4891(2) 0.0325(7) Uani 1 1 d . . .
C11 C 0.5001(4) 0.40954(19) 0.4066(2) 0.0375(8) Uani 1 1 d . . .
C12 C 0.4003(4) 0.3544(2) 0.4184(2) 0.0397(8) Uani 1 1 d . . .
C16 C 0.6182(4) 0.3985(2) 0.4657(2) 0.0417(9) Uani 1 1 d . . .
C10 C 0.4781(4) 0.4794(2) 0.3293(2) 0.0551(10) Uani 1 1 d . . .
H10B H 0.3904 0.4774 0.2953 0.083 Uiso 1 1 calc R . .
H10C H 0.5330 0.4672 0.2875 0.083 Uiso 1 1 calc R . .
H10A H 0.4970 0.5380 0.3563 0.083 Uiso 1 1 calc R . .
S31 S 0.13185(7) 0.11845(5) 0.32861(5) 0.0287(2) Uani 1 1 d . . .
O32 O 0.02481(19) 0.15639(13) 0.35951(14) 0.0341(5) Uani 1 1 d . . .
O31 O 0.22726(19) 0.07263(13) 0.39832(14) 0.0373(5) Uani 1 1 d . . .
N33 N 0.2295(2) 0.30009(15) 0.17853(17) 0.0272(6) Uani 1 1 d . . .
C37 C 0.1489(3) 0.25349(18) 0.22146(19) 0.0255(7) Uani 1 1 d . . .
N32 N 0.2101(2) 0.18947(15) 0.28190(16) 0.0265(6) Uani 1 1 d . . .
C34 C 0.0698(3) 0.04027(18) 0.2395(2) 0.0271(7) Uani 1 1 d . . .
C41 C 0.0202(3) 0.27928(19) 0.1981(2) 0.0287(7) Uani 1 1 d . . .
C39 C 0.0654(3) 0.3910(2) 0.0926(2) 0.0355(8) Uani 1 1 d . . .
C31 C -0.0234(3) -0.0786(2) 0.0925(2) 0.0366(8) Uani 1 1 d . . .
C35 C -0.0574(3) 0.0426(2) 0.1940(2) 0.0344(8) Uani 1 1 d . . .
C40 C -0.0202(3) 0.3463(2) 0.1351(2) 0.0319(7) Uani 1 1 d . . .
C32 C 0.1032(3) -0.0817(2) 0.1419(2) 0.0384(9) Uani 1 1 d . . .
C36 C -0.1034(3) -0.0165(2) 0.1210(3) 0.0395(8) Uani 1 1 d . . .
C38 C 0.1902(3) 0.36651(19) 0.1158(2) 0.0315(7) Uani 1 1 d . . .
C33 C 0.1504(3) -0.0223(2) 0.2140(2) 0.0351(8) Uani 1 1 d . . .
C30 C -0.0734(6) -0.1424(3) 0.0130(3) 0.0563(12) 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
O11 S11 O12 117.48(12) . .
O11 S11 N12 105.01(11) . .
O12 S11 N12 114.40(13) . .
O11 S11 C14 107.04(13) . .
O12 S11 C14 107.44(13) . .
N12 S11 C14 104.53(12) . .
C21 C20 C19 121.1(3) . .
C17 N12 S11 122.91(19) . .
C18 N13 C17 124.1(3) . .
C18 C19 C20 117.9(3) . .
N12 C17 N13 113.2(2) . .
N12 C17 C21 131.0(2) . .
N13 C17 C21 115.7(3) . .
C19 C18 N13 120.6(3) . .
C20 C21 C17 120.5(3) . .
C16 C15 C14 119.0(4) . .
C13 C14 C15 120.1(3) . .
C13 C14 S11 119.3(2) . .
C15 C14 S11 120.6(3) . .
C14 C13 C12 119.9(3) . .
C16 C11 C12 118.4(3) . .
C16 C11 C10 121.2(3) . .
C12 C11 C10 120.3(4) . .
C13 C12 C11 120.6(4) . .
C11 C16 C15 121.9(3) . .
O31 S31 O32 116.70(12) . .
O31 S31 N32 105.06(12) . .
O32 S31 N32 114.14(12) . .
O31 S31 C34 107.43(13) . .
O32 S31 C34 107.36(13) . .
N32 S31 C34 105.43(12) . .
C38 N33 C37 123.6(3) . .
N32 C37 N33 113.1(2) . .
N32 C37 C41 130.8(2) . .
N33 C37 C41 116.1(3) . .
C37 N32 S31 121.27(19) . .
C35 C34 C33 119.9(3) . .
C35 C34 S31 120.5(2) . .
C33 C34 S31 119.5(3) . .
C40 C41 C37 120.7(3) . .
C38 C39 C40 118.3(3) . .
C32 C31 C36 117.7(3) . .
C32 C31 C30 121.1(4) . .
C36 C31 C30 121.2(4) . .
C34 C35 C36 119.8(3) . .
C41 C40 C39 121.0(3) . .
C33 C32 C31 121.4(3) . .
C35 C36 C31 121.3(3) . .
N33 C38 C39 120.3(3) . .
C34 C33 C32 119.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S11 O11 1.436(2) .
S11 O12 1.442(2) .
S11 N12 1.604(2) .
S11 C14 1.768(3) .
C20 C21 1.362(4) .
C20 C19 1.402(4) .
N12 C17 1.360(4) .
N13 C18 1.350(4) .
N13 C17 1.366(3) .
C19 C18 1.346(4) .
C17 C21 1.405(4) .
C15 C16 1.383(5) .
C15 C14 1.391(4) .
C14 C13 1.375(4) .
C13 C12 1.388(4) .
C11 C16 1.372(5) .
C11 C12 1.392(5) .
C11 C10 1.517(4) .
S31 O31 1.443(2) .
S31 O32 1.4426(19) .
S31 N32 1.599(2) .
S31 C34 1.763(3) .
N33 C38 1.351(4) .
N33 C37 1.369(3) .
C37 N32 1.364(4) .
C37 C41 1.399(4) .
C34 C35 1.376(4) .
C34 C33 1.380(4) .
C41 C40 1.362(4) .
C39 C38 1.354(4) .
C39 C40 1.391(4) .
C31 C32 1.387(5) .
C31 C36 1.389(4) .
C31 C30 1.506(5) .
C35 C36 1.388(5) .
C32 C33 1.384(5) .
