#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:19:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216968.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_7216968
loop_
_publ_author_name
'Brigas, Amadeu, F.'
'Clegg, William'
'Dillon, Christopher J.'
'Fonseca, Custodia F. C.'
'Johnstone, Robert A. W.'
_publ_section_title
;
 Metal-assisted reactions. Part 29. Structure and hydrogenolysis of C--N
 bonds in derivatives of aromatic amines. Bond length and
 electronegativity changes from X-ray crystallographic data
;
_journal_issue                   8
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              1315
_journal_paper_doi               10.1039/b102571f
_journal_year                    2001
_chemical_formula_sum            'C14 H12 N2 O2 S'
_chemical_formula_weight         272.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 97.246(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2916(16)
_cell_length_b                   21.129(5)
_cell_length_c                   8.0546(18)
_cell_measurement_reflns_used    6167
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.63
_cell_volume                     1231.0(5)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6879
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7195
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        15
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2377
_reflns_number_total             2654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b102571f.txt
_cod_data_source_block           liv1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.2824P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.2824P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7216968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'0.5-x, 0.5+y, 0.5-z'
'0.5+x, 0.5-y, 0.5+z'
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_calc_flag
_atom_site_refinement_flags
S1 S 0.79844(5) 0.033006(17) 0.76764(5) 0.01585(14) Uani 1 d .
O1 O 0.91908(16) 0.01337(6) 0.64822(14) 0.0228(3) Uani 1 d .
O2 O 0.88688(16) 0.06427(6) 0.91317(14) 0.0237(3) Uani 1 d .
N1 N 0.63144(18) 0.07704(6) 0.67445(16) 0.0183(3) Uani 1 d .
N2 N 0.30873(18) 0.07265(6) 0.60794(16) 0.0177(3) Uani 1 d .
H2 H 0.2115 0.0489 0.6174 0.021 Uiso 1 calc R
C1 C 0.6568(2) -0.03036(7) 0.81661(19) 0.0162(3) Uani 1 d .
C2 C 0.7048(2) -0.08629(8) 0.8998(2) 0.0210(3) Uani 1 d .
H2A H 0.8295 -0.0959 0.9411 0.025 Uiso 1 calc R
C3 C 0.5610(2) -0.12773(8) 0.9199(2) 0.0232(4) Uani 1 d .
H3 H 0.5878 -0.1666 0.9771 0.028 Uiso 1 calc R
C4 C 0.3791(2) -0.11350(8) 0.8583(2) 0.0225(4) Uani 1 d .
H4 H 0.2843 -0.1430 0.8735 0.027 Uiso 1 calc R
C5 C 0.3332(2) -0.05693(8) 0.7746(2) 0.0197(3) Uani 1 d .
H5 H 0.2087 -0.0473 0.7324 0.024 Uiso 1 calc R
C6 C 0.4755(2) -0.01508(7) 0.7548(18) 0.0153(3) Uani 1 d .
C7 C 0.4712(2) 0.04841(7) 0.67418(18) 0.0155(3) Uani 1 d .
C8 C 0.2711(2) 0.13136(7) 0.52454(19) 0.0177(3) Uani 1 d .
C9 C 0.4089(2) 0.17407(7) 0.4953(2) 0.0207(3) Uani 1 d .
H9 H 0.5349 0.1644 0.5313 0.025 Uiso 1 calc R
C10 C 0.3623(2) 0.23107(8) 0.4132(2) 0.0230(4) Uani 1 d .
C11 C 0.1770(3) 0.24445(8) 0.3613(2) 0.0272(4) Uani 1 d .
H11 H 0.1438 0.2833 0.3060 0.033 Uiso 1 calc R
C12 C 0.0400(3) 0.20144(9) 0.3896(2) 0.0297(4) Uani 1 d .
H12 H -0.0859 0.2110 0.3530 0.036 Uiso 1 calc R
C13 C 0.0855(2) 0.14471(8) 0.4708(2) 0.0239(4) Uani 1 d .
H13 H -0.0082 0.1153 0.4897 0.029 Uiso 1 calc R
C14 C 0.5130(3) 0.27624(9) 0.3795(3) 0.0345(4) Uani 1 d .
H14A H 0.5639 0.2631 0.2780 0.052 Uiso 1 calc R
H14B H 0.6112 0.2760 0.4745 0.052 Uiso 1 calc R
H14C H 0.4619 0.3190 0.3640 0.052 Uiso 1 calc R
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
O2 S1 O1 115.48(7)
O2 S1 N1 110.27(7)
O1 S1 N1 109.77(7)
O2 S1 C1 112.58(7)
O1 S1 C1 110.71(7)
N1 S1 C1 96.38(7)
C7 N1 S1 110.39(11)
C7 N2 C8 129.11(14)
C2 C1 C6 122.92(15)
C2 C1 S1 129.59(13)
C6 C1 S1 107.48(11)
C1 C2 C3 116.51(15)
C4 C3 C2 121.45(15)
C3 C4 C5 121.30(16)
C6 C5 C4 117.70(15)
C5 C6 C1 120.12(14)
C5 C6 C7 130.50(14)
C1 C6 C7 109.38(13)
N1 C7 N2 124.48(14)
N1 C7 C6 116.36(13)
N2 C7 C6 119.16(14)
C9 C8 C13 120.56(15)
C9 C8 N2 123.05(14)
C13 C8 N2 116.39(15)
C8 C9 C10 120.09(16)
C11 C10 C9 119.16(16)
C11 C10 C14 121.32(15)
C9 C10 C14 119.51(16)
C12 C11 C10 120.52(16)
C13 C12 C11 120.60(16)
C12 C13 C8 119.07(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4268(12)
S1 O1 1.4438(12)
S1 N1 1.6374(13)
S1 C1 1.7657(16)
N1 C7 1.315(2)
N2 C7 1.338(2)
N2 C8 1.421(2)
C1 C2 1.382(2)
C1 C6 1.391(2)
C2 C3 1.391(2)
C3 C4 1.389(2)
C4 C5 1.392(2)
C5 C6 1.387(2)
C6 C7 1.489(2)
C8 C9 1.392(2)
C8 C13 1.397(2)
C9 C10 1.395(2)
C10 C11 1.392(3)
C10 C14 1.506(3)
C11 C12 1.390(3)
C12 C13 1.386(2)
