#------------------------------------------------------------------------------
#$Date: 2017-09-26 01:54:40 +0300 (Tue, 26 Sep 2017) $
#$Revision: 201260 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/64/4126462.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_4126462
loop_
_publ_author_name
'Liniger, Marc'
'Liu, Yiyang'
'Stoltz, Brian M.'
_publ_section_title
;
 Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation:
 Application to the Synthesis of Unusual Amino Acids.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08496
_journal_year                    2017
_chemical_formula_moiety         'C4 H11 N O2 S'
_chemical_formula_sum            'C4 H11 N O2 S'
_chemical_formula_weight         137.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874),
 SHELXL-2014,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.733(3)
_cell_length_b                   6.629(3)
_cell_length_c                   6.587(3)
_cell_measurement_reflns_used    2020
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.85
_cell_measurement_theta_min      3.07
_cell_volume                     337.7(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2014.7-1 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/3 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker KAPPA APEX II ccd'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         39.756
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0527 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0347
_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)+(0.0352P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                1770
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b08496_si_006.cif
_cod_data_source_block           a14358
_cod_original_cell_volume        337.6(2)
_cod_database_code               4126462
_shelxl_version_number           2014/6
_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.
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.894
_refine_ls_abs_structure_hooft   0.08(4)
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, z+1/2'
'-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
_atom_site_refinement_flags_occupancy
S1 S 0.5000 0.49246(7) 0.52063(10) 0.00865(8) Uani 1 2 d S T P
O1 O 0.66013(13) 0.57604(17) 0.44384(17) 0.0134(2) Uani 1 1 d . . .
N1 N 0.5000 0.5294(3) 0.7627(3) 0.0128(3) Uani 1 2 d S T P
H1 H 0.405(3) 0.496(3) 0.824(5) 0.024(6) Uiso 1 1 d . . .
C1 C 0.5000 0.2240(3) 0.4685(3) 0.0108(3) Uani 1 2 d S T P
C2 C 0.5000 0.2017(4) 0.2370(3) 0.0142(4) Uani 1 2 d S T P
H2A H 0.593(3) 0.264(3) 0.177(3) 0.018(6) Uiso 1 1 d . . .
H2B H 0.5000 0.062(6) 0.206(6) 0.033(10) Uiso 1 2 d S T P
C3 C 0.3369(2) 0.1311(2) 0.5612(2) 0.0169(3) Uani 1 1 d . . .
H3A H 0.244(3) 0.187(3) 0.507(5) 0.035(6) Uiso 1 1 d . . .
H3B H 0.338(4) 0.148(4) 0.710(4) 0.022(6) Uiso 1 1 d . . .
H3C H 0.339(3) -0.011(3) 0.538(5) 0.022(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
O1 S1 O1 117.58(10) . 4_655
O1 S1 N1 106.69(6) 4_655 .
O1 S1 N1 106.69(6) . .
O1 S1 C1 108.03(6) . .
O1 S1 C1 108.03(6) 4_655 .
N1 S1 C1 109.65(9) . .
S1 N1 H1 114.8(19) . .
C2 C1 S1 106.47(14) . .
C3 C1 S1 108.62(11) . .
C3 C1 S1 108.62(11) 4_655 .
C3 C1 C2 111.00(12) . .
C3 C1 C2 111.00(12) 4_655 .
C3 C1 C3 110.98(18) 4_655 .
C1 C2 H2A 112.4(13) . .
C1 C2 H2B 108(2) . .
H2A C2 H2B 110.6(19) . .
C1 C3 H3A 109.8(16) . .
C1 C3 H3B 110.1(16) . .
C1 C3 H3C 108.4(16) . .
H3A C3 H3B 111(2) . .
H3A C3 H3C 112(2) . .
H3B C3 H3C 106(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4478(11) .
S1 O1 1.4478(11) 4_655
S1 N1 1.6134(19) .
S1 C1 1.812(2) .
N1 H1 0.87(2) .
C1 C2 1.532(3) .
C1 C3 1.531(2) 4_655
C1 C3 1.531(2) .
C2 H2A 0.92(2) .
C2 H2B 0.95(4) .
C3 H3A 0.89(3) .
C3 H3B 0.99(2) .
C3 H3C 0.95(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87(2) 2.10(2) 2.9696(17) 174(3) 3_465
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_4
O1 S1 C1 C2 64.09(6) 4_655 .
O1 S1 C1 C2 -64.09(6) . .
O1 S1 C1 C3 55.51(14) . 4_655
O1 S1 C1 C3 -176.31(11) 4_655 4_655
O1 S1 C1 C3 176.31(11) . .
O1 S1 C1 C3 -55.51(14) 4_655 .
N1 S1 C1 C2 180.000(0) . .
N1 S1 C1 C3 60.40(11) . .
N1 S1 C1 C3 -60.40(11) . 4_655
