Metal-Catalyzed Oxa-[4+2] Cyclizations of Quinone Methides with Alkynyl Benzyl Alcohols.
Wang, Cong-Shuai; Cheng, Yu-Chun; Zhou, Ji; Mei, Guang-Jian; Wang, Shu-Liang; Shi, Feng; The Journal of organic chemistry 83 (2018) 13861–13873; doi:10.1021/acs.joc.8b02186

data_4034833
_publ_section_title
;
 Metal-Catalyzed Oxa-[4+2] Cyclizations of Quinone Methides with Alkynyl
 Benzyl Alcohols.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13861
_journal_page_last               13873
_journal_paper_doi               10.1021/acs.joc.8b02186
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C31 H36 O4'
_chemical_formula_sum            'C31 H36 O4'
_chemical_formula_weight         472.60
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                116.0560(10)
_cell_angle_beta                 102.8250(10)
_cell_angle_gamma                98.7450(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7271(9)
_cell_length_b                   12.1139(11)
_cell_length_c                   13.3466(12)
_cell_measurement_reflns_used    5198
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.37
_cell_volume                     1320.5(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8246
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         1.896
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.1612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4057
_reflns_number_total             4851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02186_si_002.cif
_cod_data_source_block           sf20170822_wcs_0m
_cod_database_code               4034833
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.966
_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:
 C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C19(H19),
 C23(H23)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              19866
_shelx_hkl_checksum              85731
_olex2_submission_special_instructions 'No special instructions were received'