[4 + 2] Cyclization of para-Quinone Methide Derivatives with Alkynes.
Mei, Guang-Jian; Xu, Shao-Li; Zheng, Wen-Qin; Bian, Chen-Yu; Shi, Feng; The Journal of organic chemistry 83 (2018) 1414–1421; doi:10.1021/acs.joc.7b02942

data_4033410
_publ_section_title
;
 [4 + 2] Cyclization of para-Quinone Methide Derivatives with Alkynes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1414
_journal_page_last               1421
_journal_paper_doi               10.1021/acs.joc.7b02942
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C30 H31 Br O3'
_chemical_formula_sum            'C30 H31 Br O3'
_chemical_formula_weight         519.46
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.4710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1179(13)
_cell_length_b                   17.7380(14)
_cell_length_c                   9.6044(7)
_cell_measurement_reflns_used    6170
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.296
_cell_volume                     2646.4(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16087
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.482
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0739 before and 0.0321 after correction. The Ratio of minimum to maximum transmission is 0.8518. The \l/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.8295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4112
_reflns_number_total             5177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02942_si_002.cif
_cod_data_source_block           sf20170725_mgj
_cod_depositor_comments
'Adding full bibliography for 4033409--4033410.cif.'
_cod_database_code               4033410
_shelx_shelxl_version_number     2014/8
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C22(H22)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              97164
_shelx_hkl_checksum              2121
_olex2_submission_special_instructions 'No special instructions were received'