Propargylic cation-induced intermolecular electrophilic addition-semipinacol rearrangement
Hui Shao; Xiao-Ming Zhang; Shao-Hua Wang; Fu-Min Zhang; Yong-Qiang Tu; Chao Yang; Chem.Commun. 50 (2014) 5691–; doi:10.1039/C3CC49650C

data_7113361
_publ_section_title
;
 Propargylic cation-induced intermolecular electrophilic
 addition-semipinacol rearrangement
;
_journal_name_full               Chem.Commun.
_journal_page_first              5691
_journal_paper_doi               10.1039/C3CC49650C
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C24 H25 N O3 S'
_chemical_formula_sum            'C24 H24 N O3 S'
_chemical_formula_weight         406.50
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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     iterative
_audit_creation_date             2013-09-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.56(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4601(16)
_cell_length_b                   12.695(3)
_cell_length_c                   13.331(2)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      19.5870
_cell_measurement_theta_min      3.4720
_cell_volume                     1074.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9900
_diffrn_measured_fraction_theta_max 0.5942
_diffrn_measurement_details
;
  1 omega  -15.00   19.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000   30.0000 23

  2 omega   41.00  101.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000    0.0000 40

  3 omega  -27.00    0.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -180.0000 18

  4 omega   -8.00   97.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000  120.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0264609000
_diffrn_orient_matrix_UB_12      0.0503596000
_diffrn_orient_matrix_UB_13      -0.0214071000
_diffrn_orient_matrix_UB_21      0.0939007000
_diffrn_orient_matrix_UB_22      0.0211464000
_diffrn_orient_matrix_UB_23      0.0290281000
_diffrn_orient_matrix_UB_31      0.0543006000
_diffrn_orient_matrix_UB_32      -0.0116015000
_diffrn_orient_matrix_UB_33      -0.0404001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.1545
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4271
_diffrn_reflns_point_group_measured_fraction_full 0.701
_diffrn_reflns_point_group_measured_fraction_max 0.595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.548
_diffrn_reflns_theta_min         3.208
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0703
_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/[\s^2^(Fo^2^)+(0.0321P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.302
_reflns_Friedel_fraction_full    0.379
_reflns_Friedel_fraction_max     0.288
_reflns_number_gt                1349
_reflns_number_total             3253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc49650c2.cif
_cod_data_source_block           dcm-sh
_cod_database_code               7113361
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
2.e :
 C25(H25)
;
_shelx_hkl_checksum              3655
_shelx_res_checksum              20598
_shelxl_version_number           2013-2