1,6-Conjugated addition-mediated [4 + 1] annulation: an approach to 2,3-dihydrobenzofurans
Liu, Lina; Yuan, Zhenbo; Pan, Rui; Zeng, Yuye; Lin, Aijun; Yao, Hequan; Huang, Yue; Organic Chemistry Frontiers 5 (2018) 623–; doi:10.1039/C7QO00846E

data_1553915
_publ_section_title
;
 1,6-Conjugated addition-mediated [4 + 1] annulation: an approach to
 2,3-dihydrobenzofurans
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              623
_journal_paper_doi               10.1039/C7QO00846E
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C29 H32 O3'
_chemical_formula_sum            'C29 H32 O3'
_chemical_formula_weight         428.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.016(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.962(5)
_cell_length_b                   10.0760(18)
_cell_length_c                   20.180(4)
_cell_measurement_reflns_used    1927
_cell_measurement_temperature    205
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      2.265
_cell_volume                     5395.5(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      205
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20538
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         1.535
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0856 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.8844. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.055
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_platon_squeeze_details          'TITL mo_2017560-lln_0m_a.res in C2/c'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0956P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3492
_reflns_number_total             6152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00846e2.cif
_cod_data_source_block           mo_2017560-lln_0m_sq_s
_cod_original_cell_volume        5395.3(17)
_cod_database_code               1553915
_shelx_shelxl_version_number     2014/7
_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
 0.84 with sigma of 0.02
 H28A-H3
 2.15 with sigma of 0.02
 H29C-H3
 2.15 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C21(H21), C1(H1), C11(H11), C14(H14), C13(H13), C5(H5), C12(H12),
 C2(H2), C3(H3A), C4(H4)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'