#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519857.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_1519857
loop_
_publ_author_name
'McDonald, E.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 ((E)-2-Benzenesulfonyl-2-cyano-vinyloxy)-acetic acid ethyl ester
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              288
_journal_year                    2007
_chemical_formula_sum            'C13 H13 N O5 S'
_chemical_formula_weight         295.30
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.723(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8005(6)
_cell_length_b                   5.17630(10)
_cell_length_c                   16.9786(6)
_cell_measurement_reflns_used    3349
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1368.70(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13652
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0566
_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)+(0.0050P)²+2.7074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                2581
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-288.cif
_cod_data_source_block           2007src0079
_cod_depositor_comments
;
Citation :
McDonald, E and Horton, Peter N. and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/288)

More at:
http://ecrystals.chem.soton.ac.uk/288/
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1519857
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.97137(16) -0.0932(5) 0.25600(15) 0.0207(5) Uani 1 1 d . . .
C2 C 0.98241(16) -0.0288(5) 0.17646(14) 0.0198(5) Uani 1 1 d . . .
C3 C 1.04277(16) -0.1385(5) 0.13991(15) 0.0207(5) Uani 1 1 d . . .
H3 H 1.0479 -0.0871 0.0872 0.025 Uiso 1 1 calc R . .
C4 C 1.16564(16) -0.3867(5) 0.13866(15) 0.0215(5) Uani 1 1 d . . .
H4A H 1.1459 -0.4022 0.0803 0.026 Uiso 1 1 calc R . .
H4B H 1.1888 -0.5562 0.1589 0.026 Uiso 1 1 calc R . .
C5 C 1.23510(16) -0.1846(5) 0.15489(14) 0.0202(5) Uani 1 1 d . . .
C6 C 1.37741(18) -0.0875(6) 0.13434(17) 0.0295(6) Uani 1 1 d . . .
H6A H 1.4139 -0.1056 0.1875 0.035 Uiso 1 1 calc R . .
H6B H 1.3572 0.0936 0.1279 0.035 Uiso 1 1 calc R . .
C7 C 1.42751(18) -0.1574(6) 0.06956(17) 0.0317(6) Uani 1 1 d . . .
H7A H 1.4459 -0.3381 0.0758 0.047 Uiso 1 1 calc R . .
H7B H 1.4781 -0.0455 0.0734 0.047 Uiso 1 1 calc R . .
H7C H 1.3912 -0.1341 0.0173 0.047 Uiso 1 1 calc R . .
C8 C 0.81373(16) 0.0119(5) 0.10469(14) 0.0200(5) Uani 1 1 d . . .
C9 C 0.75279(17) 0.0385(5) 0.15434(14) 0.0223(5) Uani 1 1 d . . .
H9 H 0.7600 0.1642 0.1957 0.027 Uiso 1 1 calc R . .
C10 C 0.68139(17) -0.1210(5) 0.14263(15) 0.0259(6) Uani 1 1 d . . .
H10 H 0.6393 -0.1057 0.1762 0.031 Uiso 1 1 calc R . .
C11 C 0.67132(17) -0.3032(5) 0.08182(15) 0.0252(5) Uani 1 1 d . . .
H11 H 0.6229 -0.4146 0.0747 0.030 Uiso 1 1 calc R . .
C12 C 0.73159(17) -0.3237(5) 0.03130(15) 0.0260(6) Uani 1 1 d . . .
H12 H 0.7234 -0.4458 -0.0111 0.031 Uiso 1 1 calc R . .
C13 C 0.80360(16) -0.1667(5) 0.04261(15) 0.0226(5) Uani 1 1 d . . .
H13 H 0.8453 -0.1808 0.0086 0.027 Uiso 1 1 calc R . .
N1 N 0.96202(16) -0.1415(5) 0.31965(13) 0.0295(5) Uani 1 1 d . . .
O1 O 1.09497(11) -0.3175(3) 0.17687(10) 0.0229(4) Uani 1 1 d . . .
O2 O 1.22666(12) 0.0215(4) 0.18610(11) 0.0278(4) Uani 1 1 d . . .
O3 O 1.30402(12) -0.2642(4) 0.12732(11) 0.0263(4) Uani 1 1 d . . .
O4 O 0.89815(12) 0.3994(3) 0.17765(10) 0.0248(4) Uani 1 1 d . . .
O5 O 0.93863(12) 0.2464(4) 0.04993(10) 0.0257(4) Uani 1 1 d . . .
S1 S 0.90927(4) 0.19205(12) 0.12425(3) 0.01951(15) 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
N1 C1 C2 179.0(3) . .
C3 C2 C1 123.0(2) . .
C3 C2 S1 119.89(19) . .
C1 C2 S1 116.99(18) . .
O1 C3 C2 120.6(2) . .
O1 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
O1 C4 C5 110.1(2) . .
O1 C4 H4A 109.6 . .
C5 C4 H4A 109.6 . .
O1 C4 H4B 109.6 . .
C5 C4 H4B 109.6 . .
H4A C4 H4B 108.2 . .
O2 C5 O3 126.1(2) . .
O2 C5 C4 124.2(2) . .
O3 C5 C4 109.7(2) . .
O3 C6 C7 107.3(2) . .
O3 C6 H6A 110.3 . .
C7 C6 H6A 110.3 . .
O3 C6 H6B 110.3 . .
C7 C6 H6B 110.3 . .
H6A C6 H6B 108.5 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 121.5(2) . .
C13 C8 S1 118.76(19) . .
C9 C8 S1 119.59(19) . .
C10 C9 C8 119.0(2) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
C9 C10 C11 120.0(2) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C10 C11 C12 120.5(2) . .
C10 C11 H11 119.8 . .
C12 C11 H11 119.8 . .
C13 C12 C11 120.1(2) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C8 118.8(2) . .
C12 C13 H13 120.6 . .
C8 C13 H13 120.6 . .
C3 O1 C4 115.58(19) . .
C5 O3 C6 117.7(2) . .
O4 S1 O5 119.88(11) . .
O4 S1 C2 107.96(11) . .
O5 S1 C2 106.67(11) . .
O4 S1 C8 108.87(12) . .
O5 S1 C8 109.32(11) . .
C2 S1 C8 102.77(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.143(3) .
C1 C2 1.430(3) .
C2 C3 1.348(3) .
C2 S1 1.756(3) .
C3 O1 1.326(3) .
C3 H3 0.9500 .
C4 O1 1.428(3) .
C4 C5 1.507(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 O2 1.208(3) .
C5 O3 1.322(3) .
C6 O3 1.466(3) .
C6 C7 1.504(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C13 1.391(3) .
C8 C9 1.390(3) .
C8 S1 1.758(3) .
C9 C10 1.385(4) .
C9 H9 0.9500 .
C10 C11 1.387(4) .
C10 H10 0.9500 .
C11 C12 1.389(4) .
C11 H11 0.9500 .
C12 C13 1.385(4) .
C12 H12 0.9500 .
C13 H13 0.9500 .
O4 S1 1.4349(18) .
O5 S1 1.4438(17) .
