#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200222.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_2200222
loop_
_publ_author_name
'Ziemer, Burkhard'
'Surygina, Oxana'
'Ehwald, Max'
_publ_section_title
;
 2-(Toluene-4-sulfonylamino)benzoyl fluoride
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o139
_journal_page_last               o140
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C14 H12 F N O3 S'
_chemical_formula_moiety         'C14 H12 F N O3 S'
_chemical_formula_sum            'C14 H12 F N O3 S'
_chemical_formula_weight         293.31
_chemical_name_systematic
;
2-(Toluene-4-sulfonylamino)benzoyl fluoride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.908(3)
_cell_length_b                   8.2396(14)
_cell_length_c                   13.925(4)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      2.9
_cell_volume                     1330.5(6)
_computing_cell_refinement       IPDS2.87
_computing_data_collection       'IPDS2.87 (Stoe & Cie, 1997)'
_computing_data_reduction        IPDS2.87
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 6.667
_diffrn_measured_fraction_theta_full .959
_diffrn_measured_fraction_theta_max .959
_diffrn_measurement_device       'Stoe IPDS'
_diffrn_measurement_method       '\f-oscill., \f-incr. = 1.5\%, 153 exposures'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .031
_diffrn_reflns_av_sigmaI/netI    .025
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8860
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .261
_exptl_absorpt_correction_T_max  .931
_exptl_absorpt_correction_T_min  .859
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .28
_refine_diff_density_max         .27
_refine_diff_density_min         -.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          .037
_refine_ls_R_factor_gt           .030
_refine_ls_shift/su_max          .009
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.2945P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .082
_reflns_number_gt                2048
_reflns_number_total             2439
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    tk6000.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1330.6(5)
_cod_database_code               2200222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_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_type_symbol
C1 .31945(11) .16595(18) .13239(10) .0210(3) Uani d . 1 C
C2 .41513(12) .2625(2) .13106(11) .0268(3) Uani d . 1 C
H2 .4496 .3263 .1868 .029 Uiso calc R 1 H
C3 .45902(13) .2639(2) .04734(12) .0303(4) Uani d . 1 C
H3 .5247 .3288 .0462 .033 Uiso calc R 1 H
C4 .40883(13) .1720(2) -.03582(11) .0293(4) Uani d . 1 C
C5 .31386(14) .0759(2) -.03227(11) .0314(4) Uani d . 1 C
H5 .2790 .0123 -.0880 .035 Uiso calc R 1 H
C6 .26902(13) .0712(2) .05169(11) .0272(3) Uani d . 1 C
H6 .2047 .0041 .0537 .030 Uiso calc R 1 H
C7 .45660(17) .1789(3) -.12715(13) .0439(5) Uani d . 1 C
H7A .4336 .2812 -.1620 .057 Uiso calc R 1 H
H7B .4264 .0876 -.1704 .057 Uiso calc R 1 H
H7C .5409 .1724 -.1084 .057 Uiso calc R 1 H
C8 .41828(12) -.03038(18) .34324(10) .0212(3) Uani d . 1 C
C9 .35881(14) -.1752(2) .31468(11) .0292(4) Uani d . 1 C
H9 .2790 -.1726 .2840 .032 Uiso calc R 1 H
C10 .41620(15) -.3226(2) .33112(12) .0345(4) Uani d . 1 C
H10 .3750 -.4201 .3110 .038 Uiso calc R 1 H
C11 .53272(15) -.3304(2) .37645(12) .0346(4) Uani d . 1 C
H11 .5708 -.4323 .3876 .038 Uiso calc R 1 H
C12 .59240(13) -.1885(2) .40508(11) .0293(4) Uani d . 1 C
H12 .6720 -.1931 .4363 .032 Uiso calc R 1 H
C13 .53704(12) -.03778(19) .38869(10) .0231(3) Uani d . 1 C
C14 .60319(13) .1112(2) .42067(10) .0269(3) Uani d . 1 C
F .71528(8) .08033(14) .46345(7) .0429(3) Uani d . 1 F
N .36022(11) .12047(17) .33194(9) .0250(3) Uani d . 1 N
H1 .4009(17) .203(3) .3561(15) .043(6) Uiso d . 1 H
O1 .16583(9) .05831(14) .22224(8) .0322(3) Uani d . 1 O
O2 .23569(9) .34048(14) .25538(8) .0312(3) Uani d . 1 O
O3 .57127(10) .24832(15) .41463(8) .0356(3) Uani d . 1 O
S .25781(3) .17382(5) .23630(3) .02227(13) Uani d . 1 S
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 .0198(6) .0233(9) .0200(7) .0033(5) .0051(5) .0005(6)
C2 .0233(7) .0330(10) .0234(8) -.0031(6) .0039(6) -.0030(6)
C3 .0238(7) .0376(11) .0314(8) -.0009(6) .0097(6) .0042(7)
C4 .0316(8) .0338(10) .0240(8) .0150(7) .0093(6) .0061(6)
C5 .0376(8) .0321(10) .0226(8) .0058(7) .0030(6) -.0071(6)
C6 .0247(7) .0261(9) .0303(8) -.0012(6) .0052(6) -.0044(6)
C7 .0539(11) .0547(14) .0287(9) .0202(9) .0211(8) .0095(8)
C8 .0274(7) .0230(9) .0145(6) .0015(6) .0071(5) .0006(5)
C9 .0308(8) .0266(10) .0293(8) -.0041(6) .0051(6) -.0013(6)
C10 .0463(10) .0230(10) .0348(9) -.0039(7) .0106(7) -.0032(7)
C11 .0468(10) .0245(10) .0346(9) .0096(7) .0132(7) .0027(7)
C12 .0315(8) .0328(10) .0244(8) .0074(7) .0078(6) .0031(6)
C13 .0283(7) .0269(9) .0155(7) -.0005(6) .0077(6) .0008(6)
C14 .0289(8) .0343(11) .0179(7) -.0051(7) .0061(6) -.0002(6)
F .0320(5) .0518(7) .0395(6) -.0102(4) -.0029(4) -.0004(5)
N .0313(7) .0215(8) .0213(6) .0012(5) .0040(5) -.0014(5)
O1 .0242(5) .0370(8) .0369(6) -.0018(5) .0101(5) .0046(5)
O2 .0385(6) .0281(7) .0296(6) .0103(5) .0134(5) .0010(5)
O3 .0428(7) .0287(8) .0357(7) -.0083(5) .0094(5) -.0042(5)
S .02115(19) .0249(2) .02186(19) .00365(14) .00718(14) .00199(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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_publ_flag
C6 C1 C2 120.99(13) yes
C6 C1 S 120.01(11) ?
C2 C1 S 118.91(11) ?
C3 C2 C1 118.91(14) yes
C3 C2 H2 120.5 ?
C1 C2 H2 120.5 ?
C2 C3 C4 121.42(15) yes
C2 C3 H3 119.3 ?
C4 C3 H3 119.3 ?
C5 C4 C3 118.47(14) yes
C5 C4 C7 121.16(16) ?
C3 C4 C7 120.37(16) ?
C4 C5 C6 121.05(14) yes
C4 C5 H5 119.5 ?
C6 C5 H5 119.5 ?
C1 C6 C5 119.14(14) yes
C1 C6 H6 120.4 ?
C5 C6 H6 120.4 ?
C4 C7 H7A 109.5 ?
C4 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C4 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C9 C8 C13 118.76(14) ?
C9 C8 N 121.02(13) ?
C13 C8 N 120.14(13) ?
C10 C9 C8 120.10(15) ?
C10 C9 H9 119.9 ?
C8 C9 H9 119.9 ?
C9 C10 C11 121.30(16) ?
C9 C10 H10 119.3 ?
C11 C10 H10 119.3 ?
C12 C11 C10 119.20(16) ?
C12 C11 H11 120.4 ?
C10 C11 H11 120.4 ?
C11 C12 C13 120.81(15) ?
C11 C12 H12 119.6 ?
C13 C12 H12 119.6 ?
C12 C13 C8 119.82(14) ?
C12 C13 C14 119.39(14) ?
C8 C13 C14 120.78(14) ?
O3 C14 F 118.44(14) ?
O3 C14 C13 129.10(14) ?
F C14 C13 112.46(14) ?
C8 N S 125.30(11) ?
C8 N H1 115.7(14) ?
S N H1 110.9(14) ?
O1 S O2 119.68(7) ?
O1 S N 109.64(7) ?
O2 S N 103.82(7) ?
O1 S C1 108.14(7) ?
O2 S C1 108.36(7) ?
N S C1 106.45(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.388(2)
C1 C2 1.393(2)
C1 S 1.7662(15)
C2 C3 1.382(2)
C2 H2 .9500
C3 C4 1.399(2)
C3 H3 .9500
C4 C5 1.391(2)
C4 C7 1.508(2)
C5 C6 1.392(2)
C5 H5 .9500
C6 H6 .9500
C7 H7A .9800
C7 H7B .9800
C7 H7C .9800
C8 C9 1.398(2)
C8 C13 1.413(2)
C8 N 1.414(2)
C9 C10 1.387(2)
C9 H9 .9500
C10 C11 1.389(2)
C10 H10 .9500
C11 C12 1.379(3)
C11 H11 .9500
C12 C13 1.400(2)
C12 H12 .9500
C13 C14 1.472(2)
C14 O3 1.189(2)
C14 F 1.3564(18)
N S 1.6481(14)
N H1 .85(2)
O1 S 1.4305(12)
O2 S 1.4344(12)
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
C6 C1 C2 C3 .6(2)
S C1 C2 C3 -176.05(12)
C1 C2 C3 C4 .6(2)
C2 C3 C4 C5 -1.0(2)
C2 C3 C4 C7 178.48(15)
C3 C4 C5 C6 .3(2)
C7 C4 C5 C6 -179.18(15)
C2 C1 C6 C5 -1.3(2)
S C1 C6 C5 175.33(12)
C4 C5 C6 C1 .8(2)
C13 C8 C9 C10 .1(2)
N C8 C9 C10 -176.63(14)
C8 C9 C10 C11 .4(2)
C9 C10 C11 C12 -.4(2)
C10 C11 C12 C13 -.2(2)
C11 C12 C13 C8 .7(2)
C11 C12 C13 C14 179.67(13)
C9 C8 C13 C12 -.6(2)
N C8 C13 C12 176.11(13)
C9 C8 C13 C14 -179.58(13)
N C8 C13 C14 -2.86(19)
C12 C13 C14 O3 -178.72(15)
C8 C13 C14 O3 .3(2)
C12 C13 C14 F .46(18)
C8 C13 C14 F 179.43(11)
C9 C8 N S -40.23(18)
C13 C8 N S 143.13(12)
C8 N S O1 56.51(14)
C8 N S O2 -174.49(11)
C8 N S C1 -60.23(14)
C6 C1 S O1 6.50(15)
C2 C1 S O1 -176.84(12)
C6 C1 S O2 -124.62(13)
C2 C1 S O2 52.03(14)
C6 C1 S N 124.24(13)
C2 C1 S N -59.10(14)