Catalyst-free [4 + 2] cyclization of para-quinone methide derivatives with homophthalic anhydrides.
Zhou, Jia-Yu; Ma, Chun; Zhang, Yi-Zhu; Wu, Qiong; Shi, Feng; Organic & biomolecular chemistry 16 (2018) 9382–9389; doi:10.1039/c8ob02776e

data_7156585
_publ_section_title
;
 Catalyst-free [4 + 2] cyclization of para-quinone methide derivatives
 with homophthalic anhydrides.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9382
_journal_page_last               9389
_journal_paper_doi               10.1039/c8ob02776e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C31 H33 Br O5'
_chemical_formula_sum            'C31 H33 Br O5'
_chemical_formula_weight         565.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-20 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                85.634(2)
_cell_angle_beta                 82.125(2)
_cell_angle_gamma                86.327(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1745(11)
_cell_length_b                   11.3873(13)
_cell_length_c                   12.2870(14)
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.02
_cell_measurement_theta_min      2.37
_cell_volume                     1404.0(3)
_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 0.981
_diffrn_measured_fraction_theta_max 0.974
_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  0.0169
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7863
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.451
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0645 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.8652. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5602
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3365
_reflns_number_total             5602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02776e2.cif
_cod_data_source_block           sf20180503_mc_0m
_cod_depositor_comments          'Adding full bibliography for 7156585.cif.'
_cod_database_code               7156585
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.521
_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, All O(H) groups
2. Restrained distances
 H3-H26C
 2 with sigma of 0.02
3.a Riding coordinates:
 O3(H3)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19),
 C23(H23)
3.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              47829
_shelx_hkl_checksum              29585
_olex2_submission_special_instructions 'No special instructions were received'