#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150260.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_7150260
loop_
_publ_author_name
'Nikolaev, Vsevolod'
'Hennig, Lothar'
'Sieler, Jochim'
'Rodina, Ludmila'
'Schulze, Barbel'
'Nikolaev, Valerij'
_publ_section_title
;
 Cyclic and acyclic sulfonimides in reactions with
 Rh(II)-ketocarbenoids: a new access to chemoselective
 O-functionalization of the imidic carbonyl groups.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4108
_journal_page_last               4116
_journal_paper_doi               10.1039/b508317f
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C12 H10 N O5 S'
_chemical_formula_weight         280.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.6470(10)
_cell_angle_beta                 97.2650(10)
_cell_angle_gamma                110.1720(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6162(5)
_cell_length_b                   9.1924(5)
_cell_length_c                   10.6592(6)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     644.88(7)
_computing_cell_refinement       'SAINT (AXS BRUKER)'
_computing_data_collection       'SMART (AXS BRUKER)'
_computing_data_reduction        'SAINT (AXS BRUKER)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'CCD Diffractometer (AXS BRUKER)'
_diffrn_measurement_method       Omega-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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4174
_diffrn_reflns_theta_full        28.64
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9364
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2596
_reflns_number_total             2907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b508317f.txt
_cod_data_source_block           c642
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150260
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1505(2) 0.34655(18) 0.56340(14) 0.0315(3) Uani 1 1 d . . .
C2 C 0.2384(2) 0.4780(2) 0.68721(16) 0.0399(3) Uani 1 1 d . . .
C3 C 0.1200(3) 0.5441(2) 0.75120(16) 0.0433(4) Uani 1 1 d . . .
C4 C -0.0776(3) 0.4807(2) 0.69253(16) 0.0407(4) Uani 1 1 d . . .
C5 C -0.1650(2) 0.34643(18) 0.56773(15) 0.0348(3) Uani 1 1 d . . .
C6 C -0.0474(2) 0.27974(16) 0.50495(14) 0.0294(3) Uani 1 1 d . . .
C7 C -0.0965(2) 0.13444(17) 0.37841(14) 0.0304(3) Uani 1 1 d . . .
C8 C -0.3256(2) -0.10418(18) 0.20099(15) 0.0343(3) Uani 1 1 d . . .
C9 C -0.2687(2) -0.0754(2) 0.07459(16) 0.0419(4) Uani 1 1 d . . .
C10 C -0.2424(4) -0.2149(3) -0.0248(2) 0.0611(6) Uani 1 1 d . . .
C11 C -0.5436(2) -0.2090(2) 0.16682(17) 0.0418(4) Uani 1 1 d . . .
C12 C -0.6686(3) -0.1256(2) 0.2193(2) 0.0461(4) Uani 1 1 d . . .
N1 N 0.03945(18) 0.09174(16) 0.34305(13) 0.0353(3) Uani 1 1 d . . .
O1 O 0.32933(18) 0.14336(16) 0.52250(13) 0.0475(3) Uani 1 1 d . . .
O2 O 0.36659(17) 0.31893(16) 0.38679(13) 0.0461(3) Uani 1 1 d . . .
O3 O -0.28037(14) 0.05212(12) 0.30935(10) 0.0334(2) Uani 1 1 d . . .
04 O -0.2457(3) 0.05450(17) 0.06194(14) 0.0625(4) Uani 1 1 d . . .
05 O -0.6025(2) -0.35506(17) 0.09749(19) 0.0760(5) Uani 1 1 d . . .
S1 S 0.24888(5) 0.22739(5) 0.45462(4) 0.03472(14) Uani 1 1 d . . .
H2 H 0.370(3) 0.518(2) 0.723(2) 0.045(5) Uiso 1 1 d . . .
H3 H 0.177(3) 0.635(3) 0.838(2) 0.048(5) Uiso 1 1 d . . .
H4 H -0.161(3) 0.525(3) 0.739(2) 0.054(6) Uiso 1 1 d . . .
H5 H -0.300(3) 0.305(2) 0.5288(19) 0.035(4) Uiso 1 1 d . . .
H8 H -0.257(3) -0.162(2) 0.2337(19) 0.037(4) Uiso 1 1 d . . .
H10A H -0.123(6) -0.209(5) 0.016(5) 0.146(16) Uiso 1 1 d . . .
H10B H -0.325(4) -0.322(4) -0.029(3) 0.088(9) Uiso 1 1 d . . .
H10C H -0.255(4) -0.202(4) -0.111(3) 0.093(9) Uiso 1 1 d . . .
H12A H -0.637(3) -0.086(3) 0.318(3) 0.058(6) Uiso 1 1 d . . .
H12B H -0.651(3) -0.035(3) 0.191(3) 0.065(7) Uiso 1 1 d . . .
H12C H -0.799(3) -0.196(3) 0.183(2) 0.058(6) Uiso 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
_geom_angle_publ_flag
C2 C1 C6 122.39(14) . . ?
C2 C1 S1 130.26(12) . . ?
C6 C1 S1 107.29(10) . . ?
C1 C2 C3 116.85(15) . . ?
C1 C2 H2 119.5(13) . . ?
C3 C2 H2 123.6(13) . . ?
C4 C3 C2 121.35(14) . . ?
C4 C3 H3 119.9(12) . . ?
C2 C3 H3 118.8(13) . . ?
C3 C4 C5 121.15(15) . . ?
C3 C4 H4 121.3(13) . . ?
C5 C4 H4 117.5(13) . . ?
C6 C5 C4 117.42(14) . . ?
C6 C5 H5 122.6(11) . . ?
C4 C5 H5 120.0(11) . . ?
C5 C6 C1 120.81(13) . . ?
C5 C6 C7 130.33(13) . . ?
C1 C6 C7 108.82(12) . . ?
N1 C7 O3 123.51(13) . . ?
N1 C7 C6 118.86(13) . . ?
O3 C7 C6 117.60(12) . . ?
O3 C8 C11 108.11(12) . . ?
O3 C8 C9 110.77(12) . . ?
C11 C8 C9 110.28(13) . . ?
O3 C8 H8 108.3(11) . . ?
C11 C8 H8 108.6(10) . . ?
C9 C8 H8 110.8(11) . . ?
04 C9 C10 124.15(17) . . ?
04 C9 C8 119.83(15) . . ?
C10 C9 C8 116.01(16) . . ?
C9 C10 H10A 104(3) . . ?
C9 C10 H10B 113.3(18) . . ?
H10A C10 H10B 100(3) . . ?
C9 C10 H10C 108.0(19) . . ?
H10A C10 H10C 117(3) . . ?
H10B C10 H10C 114(3) . . ?
05 C11 C12 124.01(16) . . ?
05 C11 C8 117.42(16) . . ?
C12 C11 C8 118.57(14) . . ?
C11 C12 H12A 110.4(13) . . ?
C11 C12 H12B 109.2(15) . . ?
H12A C12 H12B 110(2) . . ?
C11 C12 H12C 111.5(14) . . ?
H12A C12 H12C 109.8(19) . . ?
H12B C12 H12C 105.9(19) . . ?
C7 N1 S1 108.78(10) . . ?
C7 O3 C8 115.35(11) . . ?
O2 S1 O1 117.41(8) . . ?
O2 S1 N1 108.43(7) . . ?
O1 S1 N1 109.73(7) . . ?
O2 S1 C1 112.45(7) . . ?
O1 S1 C1 110.54(7) . . ?
N1 S1 C1 96.15(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(2) . ?
C1 C6 1.3886(19) . ?
C1 S1 1.7669(15) . ?
C2 C3 1.390(2) . ?
C2 H2 0.92(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.96(2) . ?
C4 C5 1.396(2) . ?
C4 H4 0.98(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.949(18) . ?
C6 C7 1.4760(18) . ?
C7 N1 1.2874(19) . ?
C7 O3 1.3215(17) . ?
C8 O3 1.4383(16) . ?
C8 C11 1.533(2) . ?
C8 C9 1.536(2) . ?
C8 H8 0.968(18) . ?
C9 04 1.198(2) . ?
C9 C10 1.488(3) . ?
C10 H10A 0.93(4) . ?
C10 H10B 0.95(3) . ?
C10 H10C 0.96(3) . ?
C11 05 1.204(2) . ?
C11 C12 1.478(3) . ?
C12 H12A 0.97(3) . ?
C12 H12B 0.94(2) . ?
C12 H12C 0.93(2) . ?
N1 S1 1.6622(13) . ?
O1 S1 1.4313(12) . ?
O2 S1 1.4308(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(2) . . . . ?
S1 C1 C2 C3 -178.17(12) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C4 C5 C6 C7 176.36(14) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
S1 C1 C6 C5 179.49(11) . . . . ?
C2 C1 C6 C7 -176.14(13) . . . . ?
S1 C1 C6 C7 1.49(14) . . . . ?
C5 C6 C7 N1 -177.05(14) . . . . ?
C1 C6 C7 N1 0.69(18) . . . . ?
C5 C6 C7 O3 1.1(2) . . . . ?
C1 C6 C7 O3 178.81(12) . . . . ?
O3 C8 C9 04 -19.6(2) . . . . ?
C11 C8 C9 04 100.08(19) . . . . ?
O3 C8 C9 C10 159.46(17) . . . . ?
C11 C8 C9 C10 -80.9(2) . . . . ?
O3 C8 C11 05 -166.04(17) . . . . ?
C9 C8 C11 05 72.7(2) . . . . ?
O3 C8 C11 C12 14.4(2) . . . . ?
C9 C8 C11 C12 -106.82(17) . . . . ?
O3 C7 N1 S1 179.36(11) . . . . ?
C6 C7 N1 S1 -2.63(17) . . . . ?
N1 C7 O3 C8 8.49(19) . . . . ?
C6 C7 O3 C8 -169.54(12) . . . . ?
C11 C8 O3 C7 160.21(12) . . . . ?
C9 C8 O3 C7 -78.86(15) . . . . ?
C7 N1 S1 O2 -113.19(11) . . . . ?
C7 N1 S1 O1 117.39(11) . . . . ?
C7 N1 S1 C1 2.96(12) . . . . ?
C2 C1 S1 O2 -72.35(16) . . . . ?
C6 C1 S1 O2 110.27(11) . . . . ?
C2 C1 S1 O1 61.02(17) . . . . ?
C6 C1 S1 O1 -116.36(11) . . . . ?
C2 C1 S1 N1 174.79(15) . . . . ?
C6 C1 S1 N1 -2.59(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4481577
