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_7113360
_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         'C27 H27 N O4 S'
_chemical_formula_sum            'C27 H27 N O4 S'
_chemical_formula_weight         461.56
_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
_atom_sites_solution_secondary   difmap
_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                70.264(10)
_cell_angle_beta                 86.034(11)
_cell_angle_gamma                81.468(9)
_cell_formula_units_Z            2
_cell_length_a                   8.4189(12)
_cell_length_b                   10.2968(8)
_cell_length_c                   14.6301(19)
_cell_measurement_reflns_used    2795
_cell_measurement_temperature    293.89(10)
_cell_measurement_theta_max      26.2260
_cell_measurement_theta_min      3.6500
_cell_volume                     1180.3(3)
_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
;
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      293.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9785
_diffrn_measured_fraction_theta_max 0.8746
_diffrn_measurement_details
;
  1 omega  -73.00  -34.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  130.0000  179.0000 26

  2 omega  -18.00   24.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000  -60.0000 28

  3 omega   43.00  104.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000 -180.0000 41

  4 omega  -10.00   98.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   19.0000 -120.0000 72

  5 omega  -75.00  -48.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  132.0000  178.0000 18

  6 omega  -62.00  -35.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262   91.0000   81.7543 18

  7 omega   50.00   87.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000    0.0000 25

  8 omega  -54.00   58.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000 -120.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0487203000
_diffrn_orient_matrix_UB_12      0.0332458000
_diffrn_orient_matrix_UB_13      -0.0413142000
_diffrn_orient_matrix_UB_21      -0.0675075000
_diffrn_orient_matrix_UB_22      0.0061629000
_diffrn_orient_matrix_UB_23      0.0307685000
_diffrn_orient_matrix_UB_31      0.0182088000
_diffrn_orient_matrix_UB_32      0.0656508000
_diffrn_orient_matrix_UB_33      -0.0012357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66807
_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    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3700
_exptl_crystal_size_mid          0.3500
_exptl_crystal_size_min          0.2400
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0086(19)
_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   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                3071
_reflns_number_total             4562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49650c2.cif
_cod_data_source_block           sh_906
_cod_original_cell_volume        1180.3(2)
_cod_database_code               7113360
_reflns_odcompleteness_completeness 97.85
_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:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.e :
 C11(H11)
;