The intramolecular 5-exo, 7-endo-dig transition metal-free cyclization sequence of (2-alkynylphenyl) benzyl ethers: synthesis of seven-membered fused benzo[b]furans
Gai, Rafaela; do Carmo Pinheiro, Roberto; Neto, José S. S.; Iglesias, Bernardo A.; Acunha, Thiago V.; Back, Davi F.; Zeni, Gilson; Green Chem. 18 (2016) 6648–; doi:10.1039/C6GC02423H

data_7226792
_publ_section_title
;
 The intramolecular 5-exo, 7-endo-dig transition metal-free cyclization
 sequence of (2-alkynylphenyl) benzyl ethers: synthesis of seven-membered
 fused benzo[b]furans
;
_journal_issue                   24
_journal_name_full               'Green Chem.'
_journal_page_first              6648
_journal_paper_doi               10.1039/C6GC02423H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C29 H19 Cl O'
_chemical_formula_sum            'C29 H19 Cl O'
_chemical_formula_weight         418.89
_chemical_melting_point          ?
_chemical_name_common
'chlorophenyl phenyl benzo cyclohepta benzofuran'
_chemical_name_systematic
;
5a-(4-chlorophenyl)-6-phenyl-5aH-benzo[4,5]cyclohepta[1,2-b]benzofuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2016-05-20T18:41:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-06-15 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.866(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5556(17)
_cell_length_b                   18.935(3)
_cell_length_c                   11.627(3)
_cell_measurement_reflns_used    9178
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.555
_cell_measurement_theta_min      2.789
_cell_volume                     2088.6(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact G'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41453
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.4
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+1.2258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                4134
_reflns_number_total             6097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc02423h2.cif
_cod_data_source_block           test33
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226790--7226792.cif.
;
_cod_original_cell_volume        2088.7(7)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7226792
_solvent_exptl_crystal_recrystallization_method CH3OH/CH2Cl2