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_7113362
_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         'C13 H16 O2'
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90.00
_cell_angle_beta                 115.695(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5769(11)
_cell_length_b                   7.8178(4)
_cell_length_c                   12.5456(8)
_cell_measurement_reflns_used    843
_cell_measurement_temperature    293.83(10)
_cell_measurement_theta_max      23.2920
_cell_measurement_theta_min      3.8310
_cell_volume                     1111.55(16)
_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      293.83(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.8302
_diffrn_measured_fraction_theta_max 0.7198
_diffrn_measurement_details
;
  1 omega  -76.00  -48.40   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -57.0000 -120.0000 23

  2 omega  -21.00    4.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -57.0000 -120.0000 21

  3 omega  -50.00   65.20   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000   60.0000 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0207376000
_diffrn_orient_matrix_UB_12      0.0852908000
_diffrn_orient_matrix_UB_13      -0.0043984000
_diffrn_orient_matrix_UB_21      -0.0197019000
_diffrn_orient_matrix_UB_22      -0.0026148000
_diffrn_orient_matrix_UB_23      -0.0621973000
_diffrn_orient_matrix_UB_31      -0.0556713000
_diffrn_orient_matrix_UB_32      -0.0308284000
_diffrn_orient_matrix_UB_33      -0.0069299000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2951
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53484
_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_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.037(8)
_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   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1992
_reflns_number_gt                1215
_reflns_number_total             1851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc49650c2.cif
_cod_data_source_block           sh988_2
_cod_original_cell_volume        1111.56(14)
_cod_database_code               7113362
_reflns_odcompleteness_completeness 83.02
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B)
2.c :
 C9(H9)
;