Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: metal-free and economical synthesis of arylcyclobutenals
Ohno, Shohei; Avena, Ramon Francisco; Aoyama, Hiroshi; Fujioka, Hiromichi; Arisawa, Mitsuhiro; Green Chemistry 22 (2020) 1220–1228; doi:10.1039/C9GC04184B

data_7239750
_publ_section_title
;
 Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols
 followed by the nucleophilic addition of water: metal-free and economical
 synthesis of arylcyclobutenals
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1220
_journal_page_last               1228
_journal_paper_doi               10.1039/C9GC04184B
_journal_volume                  22
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H29 O2 Si1'
_chemical_formula_sum            'C40 H58 O4 Si2'
_chemical_formula_weight         659.04
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2017-08-04T14:07:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-10-12 deposited with the CCDC.	2020-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.828(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.510(3)
_cell_length_b                   11.377(3)
_cell_length_c                   32.058(9)
_cell_measurement_reflns_used    30670
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.885
_cell_measurement_wavelength     1.54178
_cell_volume                     3824.7(18)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'quarter \C-circle diffractometer'
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_UB_11      0.022941
_diffrn_orient_matrix_UB_12      -0.07671
_diffrn_orient_matrix_UB_13      0.013752
_diffrn_orient_matrix_UB_21      -0.09157
_diffrn_orient_matrix_UB_22      -0.024411
_diffrn_orient_matrix_UB_23      -0.002839
_diffrn_orient_matrix_UB_31      0.013476
_diffrn_orient_matrix_UB_32      -0.035285
_diffrn_orient_matrix_UB_33      -0.027932
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            39424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         4.124
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1562P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2602
_reflns_number_gt                4701
_reflns_number_total             6995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc04184b3.cif
_cod_data_source_block           ddd
_cod_depositor_comments
;Adding full bibliography for 7239750.cif.

 Adding full bibliography for 7239750.cif.
;
_cod_original_cell_volume        3825.0(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239750