Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol.
Han, Ya-Ping; Song, Xian-Rong; Qiu, Yi-Feng; Li, Xue-Song; Zhang, Heng-Rui; Zhu, Xin-Yu; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 18 (2016) 3866–3869; doi:10.1021/acs.orglett.6b01875

data_1555661
_publ_section_title
;
 Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with
 2-Vinylphenol.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3866
_journal_page_last               3869
_journal_paper_doi               10.1021/acs.orglett.6b01875
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C31 H26 O'
_chemical_formula_sum            'C31 H26 O'
_chemical_formula_weight         414.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                100.200(6)
_cell_angle_beta                 94.644(6)
_cell_angle_gamma                113.781(7)
_cell_formula_units_Z            4
_cell_length_a                   11.2411(8)
_cell_length_b                   11.9761(9)
_cell_length_c                   19.9127(14)
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    289.7(8)
_cell_measurement_theta_max      21.7350
_cell_measurement_theta_min      3.7180
_cell_volume                     2379.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289.7(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   23.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000   60.0000 66

  2 omega    2.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000 -120.0000 38

  3 omega  -24.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -150.0000 63

  4 omega  -18.00   10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -120.0000 28

  5 omega  -14.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 38

  6 omega  -19.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -30.0000 71

  7 omega  -48.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   90.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0591513000
_diffrn_orient_matrix_UB_12      0.0551117000
_diffrn_orient_matrix_UB_13      0.0039610000
_diffrn_orient_matrix_UB_21      -0.0329018000
_diffrn_orient_matrix_UB_22      0.0232431000
_diffrn_orient_matrix_UB_23      -0.0218309000
_diffrn_orient_matrix_UB_31      -0.0176997000
_diffrn_orient_matrix_UB_32      0.0290725000
_diffrn_orient_matrix_UB_33      0.0292611000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.1259
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16738
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1852
_refine_ls_R_factor_gt           0.0728
_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^)+(0.0511P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.2031
_reflns_number_gt                3799
_reflns_number_total             9346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01875_si_002.cif
_cod_data_source_block           hanyp_0410_2
_cod_database_code               1555661
_reflns_odcompleteness_completeness 99.78
_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:
 C7(H7), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29),
  C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C43(H43), C44(H44),
 C45(H45), C46(H46), C47(H47), C50(H50), C51(H51), C53(H53), C54(H54), C57(H57),
  C58(H58), C60(H60), C61(H61)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C55(H55A,H55B,H55C), C62(H62A,H62B,
 H62C)
;
_olex2_date_sample_data_collection 2016-04-11
_olex2_submission_special_instructions 'No special instructions were received'