#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/53/2235330.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_2235330
loop_
_publ_author_name
'Li, Ying-Hua'
'Xu, Hong-Wu'
'Zhang, Liu-Xue'
_publ_section_title
;
 Methyl (R)-2-(2-chlorophenyl)-2-(3-nitrophenylsulfonyloxy)acetate
;
_journal_coeditor_code           ZL2477
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1689
_journal_paper_doi               10.1107/S1600536812020016
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H12 Cl N O7 S'
_chemical_formula_moiety         'C15 H12 Cl N O7 S'
_chemical_formula_sum            'C15 H12 Cl N O7 S'
_chemical_formula_weight         385.77
_chemical_name_systematic
;
Methyl (R)-2-(2-chlorophenyl)-2-(3-nitrophenylsulfonyloxy)acetate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5791(3)
_cell_length_b                   11.0242(5)
_cell_length_c                   19.6736(7)
_cell_measurement_reflns_used    1814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3130
_cell_measurement_theta_min      3.2553
_cell_volume                     1643.80(11)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL/PC (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5654
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.26
_diffrn_standards_interval_time  8
_diffrn_standards_number         5675
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.9175
_exptl_absorpt_correction_T_min  0.8898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.206
_refine_ls_abs_structure_details 'Flack (1983), 1209 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0389
_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)+(0.0393P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2680
_reflns_number_total             3153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2477.cif
_cod_data_source_block           I
_cod_database_code               2235330
_cod_database_fobs_code          2235330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
S S1 0.47477(9) 0.03812(6) 0.23919(4) 0.03772(18) Uani d . 1 1
Cl Cl1 -0.05655(10) 0.08212(8) 0.36889(4) 0.0513(2) Uani d . 1 1
N N1 0.2766(4) 0.3236(3) 0.04654(14) 0.0554(7) Uani d . 1 1
O O7 0.1312(4) 0.2781(3) 0.05356(13) 0.0763(8) Uani d . 1 1
O O6 0.3113(4) 0.4007(2) 0.00436(14) 0.0820(8) Uani d . 1 1
O O5 0.4263(3) -0.06820(17) 0.20270(10) 0.0474(5) Uani d . 1 1
O O4 0.6140(3) 0.0334(2) 0.28718(11) 0.0540(6) Uani d . 1 1
O O2 0.1443(3) 0.36269(18) 0.33486(10) 0.0449(5) Uani d . 1 1
O O1 0.0857(3) 0.2602(2) 0.23895(10) 0.0544(6) Uani d . 1 1
O O3 0.2979(2) 0.07757(16) 0.27557(9) 0.0342(4) Uani d . 1 1
C C10 0.3826(4) 0.1918(3) 0.13767(14) 0.0400(7) Uani d . 1 1
H H1A 0.2728 0.1541 0.1383 0.048 Uiso calc R 1 1
C C11 0.4194(4) 0.2837(3) 0.09275(14) 0.0417(7) Uani d . 1 1
C C12 0.5830(4) 0.3385(3) 0.08930(16) 0.0496(8) Uani d . 1 1
H H3 0.6055 0.3984 0.0571 0.060 Uiso calc R 1 1
C C13 0.7118(4) 0.3032(3) 0.13422(17) 0.0504(8) Uani d . 1 1
H H4 0.8222 0.3399 0.1327 0.061 Uiso calc R 1 1
C C14 0.6791(4) 0.2137(3) 0.18141(16) 0.0442(7) Uani d . 1 1
H H5 0.7656 0.1913 0.2125 0.053 Uiso calc R 1 1
C C9 0.5149(4) 0.1576(2) 0.18190(13) 0.0369(6) Uani d . 1 1
C C1 0.1619(4) 0.2713(3) 0.29162(14) 0.0371(6) Uani d . 1 1
C C15 0.0212(4) 0.4558(3) 0.31462(17) 0.0591(9) Uani d . 1 1
H H8A 0.0540 0.4868 0.2708 0.089 Uiso calc R 1 1
H H8B 0.0231 0.5204 0.3473 0.089 Uiso calc R 1 1
H H8C -0.0954 0.4221 0.3123 0.089 Uiso calc R 1 1
C C2 0.3017(3) 0.1846(2) 0.31890(13) 0.0336(6) Uani d . 1 1
H H9 0.4171 0.2235 0.3133 0.040 Uiso calc R 1 1
C C3 0.2823(4) 0.1498(2) 0.39238(14) 0.0352(6) Uani d . 1 1
C C8 0.4258(4) 0.1657(3) 0.43647(15) 0.0473(7) Uani d . 1 1
H H11 0.5314 0.1963 0.4196 0.057 Uiso calc R 1 1
C C7 0.4125(5) 0.1367(3) 0.50432(17) 0.0584(9) Uani d . 1 1
H H12 0.5084 0.1482 0.5331 0.070 Uiso calc R 1 1
C C6 0.2564(5) 0.0905(3) 0.52935(15) 0.0588(10) Uani d . 1 1
H H13 0.2472 0.0717 0.5753 0.071 Uiso calc R 1 1
C C5 0.1147(5) 0.0719(3) 0.48751(15) 0.0495(8) Uani d . 1 1
H H14 0.0108 0.0391 0.5046 0.059 Uiso calc R 1 1
C C4 0.1279(4) 0.1026(3) 0.41929(13) 0.0378(7) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle
O4 S1 O5 1 119.91(14)
O4 S1 O5 . 119.91(14)
O4 S1 O3 1 109.87(11)
O4 S1 O3 . 109.87(11)
O5 S1 O3 . 103.66(11)
O4 S1 C9 1 108.98(13)
O4 S1 C9 . 108.98(13)
O5 S1 C9 . 109.75(12)
O3 S1 C9 . 103.33(12)
O6 N1 O7 . 124.1(3)
O6 N1 C11 . 117.9(3)
O7 N1 C11 . 118.0(3)
C1 O2 C15 . 115.4(2)
C2 O3 S1 . 118.10(15)
C11 C10 C9 . 117.4(3)
C11 C10 H1A . 121.3
C9 C10 H1A . 121.3
C10 C11 C12 . 122.5(3)
C10 C11 N1 . 117.7(3)
C12 C11 N1 . 119.8(3)
C13 C12 C11 . 118.8(3)
C13 C12 H3 . 120.6
C11 C12 H3 . 120.6
C12 C13 C14 . 120.6(3)
C12 C13 H4 . 119.7
C14 C13 H4 . 119.7
C13 C14 C9 . 119.0(3)
C13 C14 H5 . 120.5
C9 C14 H5 . 120.5
C10 C9 C14 . 121.6(3)
C10 C9 S1 . 118.9(2)
C14 C9 S1 . 119.5(2)
O1 C1 O2 . 125.9(3)
O1 C1 C2 . 125.3(3)
O2 C1 C2 . 108.7(2)
O2 C15 H8A . 109.5
O2 C15 H8B . 109.5
H8A C15 H8B . 109.5
O2 C15 H8C . 109.5
H8A C15 H8C . 109.5
H8B C15 H8C . 109.5
O3 C2 C3 . 110.7(2)
O3 C2 C1 . 106.7(2)
C3 C2 C1 . 115.5(2)
O3 C2 H9 . 107.9
C3 C2 H9 . 107.9
C1 C2 H9 . 107.9
C4 C3 C8 . 117.7(3)
C4 C3 C2 . 123.1(2)
C8 C3 C2 . 119.2(3)
C7 C8 C3 . 121.0(3)
C7 C8 H11 . 119.5
C3 C8 H11 . 119.5
C8 C7 C6 . 119.6(3)
C8 C7 H12 . 120.2
C6 C7 H12 . 120.2
C5 C6 C7 . 120.9(3)
C5 C6 H13 . 119.5
C7 C6 H13 . 119.5
C6 C5 C4 . 119.3(3)
C6 C5 H14 . 120.4
C4 C5 H14 . 120.4
C3 C4 C5 . 121.4(3)
C3 C4 Cl1 . 120.9(2)
C5 C4 Cl1 . 117.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O4 1 1.417(2)
S1 O4 . 1.417(2)
S1 O5 . 1.423(2)
S1 O3 . 1.5809(18)
S1 C9 . 1.760(3)
Cl1 C4 . 1.728(3)
N1 O6 . 1.217(3)
N1 O7 . 1.218(4)
N1 C11 . 1.480(4)
O2 C1 . 1.326(3)
O2 C15 . 1.443(3)
O1 C1 . 1.192(3)
O3 C2 . 1.456(3)
C10 C11 . 1.373(4)
C10 C9 . 1.380(4)
C10 H1A . 0.9300
C11 C12 . 1.381(4)
C12 C13 . 1.374(4)
C12 H3 . 0.9300
C13 C14 . 1.377(4)
C13 H4 . 0.9300
C14 C9 . 1.390(4)
C14 H5 . 0.9300
C1 C2 . 1.524(4)
C15 H8A . 0.9600
C15 H8B . 0.9600
C15 H8C . 0.9600
C2 C3 . 1.503(4)
C2 H9 . 0.9800
C3 C4 . 1.386(4)
C3 C8 . 1.402(4)
C8 C7 . 1.376(4)
C8 H11 . 0.9300
C7 C6 . 1.379(5)
C7 H12 . 0.9300
C6 C5 . 1.368(4)
C6 H13 . 0.9300
C5 C4 . 1.388(4)
C5 H14 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C14 H5 O4 1 0.93 2.55 2.920(4) 104.1
C14 H5 O1 1_655 0.93 2.60 3.323(4) 135.4
C15 H8C O5 3_555 0.96 2.53 3.419(4) 154.5
C4 Cl1 O4 1_455 1.728(3) 3.018(2) 4.744(4) 176.27(12)
