Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides.
Zhang, Hang; Wang, Bo; Yi, Heng; Zhang, Yan; Wang, Jianbo; Organic letters 17 (2015) 3322–3325; doi:10.1021/acs.orglett.5b01542

data_1520547
_publ_section_title
;
 Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived
 from Cyclopropenes and Sulfides.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3322
_journal_page_last               3325
_journal_paper_doi               10.1021/acs.orglett.5b01542
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C25 H24 S'
_chemical_formula_sum            'C25 H24 S'
_chemical_formula_weight         356.50
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                97.999(7)
_cell_angle_beta                 97.992(6)
_cell_angle_gamma                108.357(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4128(7)
_cell_length_b                   9.6074(8)
_cell_length_c                   12.0794(9)
_cell_measurement_reflns_used    2586
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.1920
_cell_measurement_theta_min      3.7430
_cell_volume                     1007.08(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.8596
_diffrn_measurement_details
;
  1 omega  -54.00   43.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       13.7753  -57.0000  150.0000 97

  2 omega  -12.00   88.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       13.7753   49.0000  -53.0000 100

  3 omega  -20.00    5.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  -99.0000   30.0000 25

  4 omega  -81.00   18.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  -77.0000   30.0000 99

  5 omega -103.00  -78.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  178.0000  -90.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0641640000
_diffrn_orient_matrix_UB_12      -0.0657744000
_diffrn_orient_matrix_UB_13      -0.0220624000
_diffrn_orient_matrix_UB_21      -0.0371320000
_diffrn_orient_matrix_UB_22      0.0417397000
_diffrn_orient_matrix_UB_23      -0.0294696000
_diffrn_orient_matrix_UB_31      0.0324908000
_diffrn_orient_matrix_UB_32      -0.0148489000
_diffrn_orient_matrix_UB_33      -0.0479500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.121
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description
;
;
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.0886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3060
_reflns_number_total             3963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01542_si_001.cif
_cod_data_source_block           14oct09d
_cod_depositor_comments          'Adding full bibliography for 1520547.cif.'
_cod_original_cell_volume        1007.09(14)
_cod_database_code               1520547
_chemical_oxdiff_formula         'C25 H24 S'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_shelxl_version_number           2013-3