#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:40:30 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202675 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/29/4032902.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_4032902
loop_
_publ_author_name
'Chang, Meng-Yang'
'Chen, Han-Yu'
'Wang, Heui-Sin'
_publ_section_title
;
 Regiocontrolled Synthesis of α-Sulfonylmethyl o-Nitrostyrenes via
 ZnI2-Mediated Sulfonylation and AgNO2/Pd(PPh3)4-Promoted o-Nitration.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10601
_journal_page_last               10610
_journal_paper_doi               10.1021/acs.joc.7b02311
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C10 H11 N O4 S'
_chemical_formula_weight         241.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                80.149(2)
_cell_angle_beta                 78.645(2)
_cell_angle_gamma                89.534(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1934(7)
_cell_length_b                   7.9479(7)
_cell_length_c                   9.7888(9)
_cell_measurement_reflns_used    5973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4424
_cell_measurement_theta_min      2.8893
_cell_volume                     540.42(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0288P)²+0.3611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2093
_reflns_number_total             2206
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02311_si_001.cif
_cod_data_source_block           mo_161239LT_0m_a_4c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032901--4032905.cif.
;
_cod_database_code               4032902
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.24237(18) 0.05251(16) 0.05788(14) 0.0159(3) Uani 1 1 d . .
H1A H 0.3190 0.0145 0.1293 0.024 Uiso 1 1 calc R U
H1B H 0.3262 0.0901 -0.0341 0.024 Uiso 1 1 calc R U
H1C H 0.1600 -0.0422 0.0514 0.024 Uiso 1 1 calc R U
C2 C 0.26744(17) 0.38924(15) 0.10833(13) 0.0111(2) Uani 1 1 d . .
H2A H 0.3520 0.4165 0.0141 0.013 Uiso 1 1 calc R U
H2B H 0.1971 0.4933 0.1265 0.013 Uiso 1 1 calc R U
C3 C 0.38659(17) 0.34065(15) 0.21926(13) 0.0111(2) Uani 1 1 d . .
C4 C 0.55006(18) 0.26306(17) 0.18949(14) 0.0160(3) Uani 1 1 d . .
H4A H 0.6190 0.2256 0.2620 0.019 Uiso 1 1 calc R U
H4B H 0.5980 0.2450 0.0957 0.019 Uiso 1 1 calc R U
C5 C 0.31030(17) 0.36951(16) 0.36672(13) 0.0117(2) Uani 1 1 d . .
C6 C 0.25564(19) 0.22644(17) 0.47149(14) 0.0173(3) Uani 1 1 d . .
H6 H 0.2657 0.1160 0.4464 0.021 Uiso 1 1 calc R U
C7 C 0.1869(2) 0.24180(19) 0.61166(14) 0.0209(3) Uani 1 1 d . .
H7 H 0.1516 0.1422 0.6809 0.025 Uiso 1 1 calc R U
C8 C 0.16954(19) 0.40147(19) 0.65098(14) 0.0198(3) Uani 1 1 d . .
H8 H 0.1222 0.4113 0.7469 0.024 Uiso 1 1 calc R U
C9 C 0.22123(18) 0.54641(18) 0.55034(14) 0.0162(3) Uani 1 1 d . .
H9 H 0.2087 0.6565 0.5761 0.019 Uiso 1 1 calc R U
C10 C 0.29179(17) 0.52871(16) 0.41099(13) 0.0124(2) Uani 1 1 d . .
N1 N 0.35552(15) 0.68758(14) 0.31194(11) 0.0142(2) Uani 1 1 d . .
O1 O 0.00058(13) 0.28308(11) -0.00551(10) 0.0156(2) Uani 1 1 d . .
O2 O -0.00774(13) 0.17112(12) 0.24712(10) 0.0164(2) Uani 1 1 d . .
O3 O 0.42066(14) 0.68020(12) 0.18721(10) 0.0183(2) Uani 1 1 d . .
O4 O 0.34502(18) 0.82228(13) 0.35732(11) 0.0311(3) Uani 1 1 d . .
S1 S 0.10231(4) 0.22338(4) 0.10636(3) 0.01023(10) 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'
S S 0.1246 0.1234 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
S1 C1 H1A 109.5
S1 C1 H1B 109.5
H1A C1 H1B 109.5
S1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 S1 112.59(8)
C3 C2 H2A 109.1
S1 C2 H2A 109.1
C3 C2 H2B 109.1
S1 C2 H2B 109.1
H2A C2 H2B 107.8
C4 C3 C5 120.26(11)
C4 C3 C2 120.87(11)
C5 C3 C2 118.72(10)
C3 C4 H4A 120.0
C3 C4 H4B 120.0
H4A C4 H4B 120.0
C6 C5 C10 116.29(11)
C6 C5 C3 117.89(11)
C10 C5 C3 125.81(11)
C7 C6 C5 121.56(13)
C7 C6 H6 119.2
C5 C6 H6 119.2
C8 C7 C6 120.40(13)
C8 C7 H7 119.8
C6 C7 H7 119.8
C9 C8 C7 119.85(12)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C10 119.02(12)
C8 C9 H9 120.5
C10 C9 H9 120.5
C9 C10 C5 122.87(12)
C9 C10 N1 115.87(11)
C5 C10 N1 121.20(11)
O4 N1 O3 122.35(11)
O4 N1 C10 118.66(11)
O3 N1 C10 118.97(10)
O2 S1 O1 117.58(5)
O2 S1 C1 108.90(6)
O1 S1 C1 107.92(6)
O2 S1 C2 109.16(6)
O1 S1 C2 107.39(6)
C1 S1 C2 105.19(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 S1 1.7592(13)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.5101(16)
C2 S1 1.7867(12)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.3277(18)
C3 C5 1.4956(17)
C4 H4A 0.9500
C4 H4B 0.9500
C5 C6 1.3960(18)
C5 C10 1.4031(17)
C6 C7 1.3897(19)
C6 H6 0.9500
C7 C8 1.386(2)
C7 H7 0.9500
C8 C9 1.382(2)
C8 H8 0.9500
C9 C10 1.3892(18)
C9 H9 0.9500
C10 N1 1.4697(16)
N1 O4 1.2237(15)
N1 O3 1.2299(14)
O1 S1 1.4464(9)
O2 S1 1.4414(9)
