#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:19:30 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178945 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/74/4117434.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_4117434
loop_
_publ_author_name
'Nicklas Selander'
'Valery V. Fokin'
_publ_section_title
;
 Rhodium(II)-Catalyzed Asymmetric Sulfur(VI) Reduction of Diazo
 Sulfonylamidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2477
_journal_page_last               2480
_journal_paper_doi               10.1021/ja210180q
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C19 H22 N2 O2 S'
_chemical_formula_weight         342.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 108.8560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9740(7)
_cell_length_b                   8.3505(7)
_cell_length_c                   12.4633(10)
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.40
_cell_volume                     883.84(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6135
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                2906
_reflns_number_total             2964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210180q_si_004.cif
_cod_data_source_block           fokin10
_cod_database_code               4117434
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
S1 S 0.18499(4) 0.55586(5) 0.78483(3) 0.01832(11) Uani 1 1 d .
O1 O 0.13442(14) 0.46188(15) 0.86805(10) 0.0250(3) Uani 1 1 d .
O2 O 0.39808(12) 0.57906(16) 0.59791(9) 0.0229(3) Uani 1 1 d .
N1 N 0.37126(15) 0.61924(17) 0.85238(11) 0.0198(3) Uani 1 1 d .
N2 N 0.62032(15) 0.63432(19) 0.83808(11) 0.0204(3) Uani 1 1 d .
C1 C 0.4174(2) 0.2348(2) 0.77919(15) 0.0234(4) Uani 1 1 d .
H1A H 0.4283 0.2894 0.8482 0.028 Uiso 1 1 calc R
C2 C 0.4045(2) 0.0697(3) 0.77428(16) 0.0297(4) Uani 1 1 d .
H2A H 0.4036 0.0111 0.8394 0.036 Uiso 1 1 calc R
C3 C 0.3928(2) -0.0105(3) 0.67427(17) 0.0305(4) Uani 1 1 d .
H3A H 0.3846 -0.1239 0.6714 0.037 Uiso 1 1 calc R
C4 C 0.39292(18) 0.0744(3) 0.57856(15) 0.0274(4) Uani 1 1 d .
H4A H 0.3868 0.0188 0.5107 0.033 Uiso 1 1 calc R
C5 C 0.40202(18) 0.2396(2) 0.58180(14) 0.0217(4) Uani 1 1 d .
H5A H 0.3999 0.2976 0.5157 0.026 Uiso 1 1 calc R
C6 C 0.41442(17) 0.3218(2) 0.68216(14) 0.0197(4) Uani 1 1 d .
C7 C 0.42318(17) 0.4980(2) 0.68338(13) 0.0183(4) Uani 1 1 d .
C8 C 0.47068(17) 0.5856(2) 0.79813(13) 0.0172(4) Uani 1 1 d .
C9 C 0.6745(2) 0.7352(2) 0.93941(14) 0.0262(4) Uani 1 1 d .
H9A H 0.5840 0.7886 0.9515 0.039 Uiso 1 1 calc R
H9B H 0.7480 0.8160 0.9291 0.039 Uiso 1 1 calc R
H9C H 0.7279 0.6686 1.0054 0.039 Uiso 1 1 calc R
C10 C 0.73591(19) 0.6048(2) 0.77993(15) 0.0224(4) Uani 1 1 d .
H10A H 0.6985 0.5179 0.7249 0.034 Uiso 1 1 calc R
H10B H 0.8369 0.5744 0.8356 0.034 Uiso 1 1 calc R
H10C H 0.7497 0.7022 0.7404 0.034 Uiso 1 1 calc R
C11 C 0.08997(17) 0.7477(2) 0.77026(13) 0.0167(3) Uani 1 1 d .
C12 C 0.08697(18) 0.8391(2) 0.86452(13) 0.0189(3) Uani 1 1 d .
C13 C -0.00012(19) 0.9794(2) 0.84403(14) 0.0218(4) Uani 1 1 d .
H13A H -0.0043 1.0416 0.9068 0.026 Uiso 1 1 calc R
C14 C -0.08201(18) 1.0327(2) 0.73473(14) 0.0208(4) Uani 1 1 d .
C15 C -0.07617(18) 0.9396(2) 0.64399(14) 0.0202(4) Uani 1 1 d .
H15A H -0.1320 0.9740 0.5691 0.024 Uiso 1 1 calc R
C16 C 0.00890(18) 0.7974(2) 0.65921(14) 0.0194(4) Uani 1 1 d .
C17 C -0.1727(2) 1.1874(2) 0.71636(15) 0.0273(4) Uani 1 1 d .
H17A H -0.2244 1.2043 0.6350 0.041 Uiso 1 1 calc R
H17B H -0.1003 1.2762 0.7476 0.041 Uiso 1 1 calc R
H17C H -0.2524 1.1824 0.7546 0.041 Uiso 1 1 calc R
C18 C 0.01368(19) 0.7048(2) 0.55544(14) 0.0253(4) Uani 1 1 d .
H18A H -0.0517 0.7595 0.4867 0.038 Uiso 1 1 calc R
H18B H -0.0267 0.5963 0.5577 0.038 Uiso 1 1 calc R
H18C H 0.1225 0.6990 0.5549 0.038 Uiso 1 1 calc R
C19 C 0.1747(2) 0.7932(3) 0.98588(14) 0.0261(4) Uani 1 1 d .
H19D H 0.1166 0.8320 1.0352 0.039 Uiso 1 1 calc R
H19A H 0.2798 0.8414 1.0093 0.039 Uiso 1 1 calc R
H19B H 0.1843 0.6763 0.9919 0.039 Uiso 1 1 calc R
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
O1 S1 N1 107.05(7)
O1 S1 C11 107.46(7)
N1 S1 C11 97.55(7)
C8 N1 S1 113.75(11)
C8 N2 C9 120.69(13)
C8 N2 C10 123.46(14)
C9 N2 C10 115.62(13)
C2 C1 C6 119.97(17)
C1 C2 C3 120.07(18)
C4 C3 C2 120.32(19)
C5 C4 C3 120.06(18)
C4 C5 C6 120.16(17)
C5 C6 C1 119.39(17)
C5 C6 C7 119.17(15)
C1 C6 C7 121.44(16)
O2 C7 C6 123.41(16)
O2 C7 C8 117.75(16)
C6 C7 C8 118.82(14)
N1 C8 N2 120.79(14)
N1 C8 C7 123.39(13)
N2 C8 C7 115.73(13)
C16 C11 C12 121.29(16)
C16 C11 S1 116.21(12)
C12 C11 S1 122.36(13)
C13 C12 C11 117.78(15)
C13 C12 C19 118.63(15)
C11 C12 C19 123.58(16)
C12 C13 C14 122.52(16)
C15 C14 C13 118.05(16)
C15 C14 C17 121.22(15)
C13 C14 C17 120.73(16)
C14 C15 C16 122.07(16)
C15 C16 C11 118.29(15)
C15 C16 C18 118.91(15)
C11 C16 C18 122.78(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4838(12)
S1 N1 1.6952(13)
S1 C11 1.7962(18)
O2 C7 1.220(2)
N1 C8 1.312(2)
N2 C8 1.336(2)
N2 C9 1.464(2)
N2 C10 1.4656(19)
C1 C2 1.384(3)
C1 C6 1.403(2)
C2 C3 1.388(3)
C3 C4 1.388(3)
C4 C5 1.382(3)
C5 C6 1.399(2)
C6 C7 1.474(3)
C7 C8 1.539(2)
C11 C16 1.402(2)
C11 C12 1.408(2)
C12 C13 1.385(3)
C12 C19 1.512(2)
C13 C14 1.395(2)
C14 C15 1.387(2)
C14 C17 1.504(3)
C15 C16 1.391(3)
C16 C18 1.519(2)
