Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne and phenol
Wang, Yu-Jiang; Zhang, Yuan; Qiang, Zou; Liang, Jia-Ying; Chen, Zili; Chemical Communications  (2021) –; doi:10.1039/D1CC05260H

data_7129219
_publ_section_title
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 Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne
 and phenol
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05260H
_journal_year                    2021
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-09-01 deposited with the CCDC.	2021-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9976(6)
_cell_length_b                   32.7715(15)
_cell_length_c                   5.6389(2)
_cell_measurement_reflns_used    6023
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.740
_cell_measurement_theta_min      2.696
_cell_volume                     2586.69(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11389
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.759
_diffrn_reflns_theta_min         2.697
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1596 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.1284.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1054P)^2^+0.0509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.509
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.619
_reflns_number_gt                4044
_reflns_number_total             4345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05260h2.cif
_cod_data_source_block           cu_0312_3_0m
_cod_database_code               7129219
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H00Z), C012(H012)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00F,H00G), C8(H00K,H00L), C10(H00M,H00O), C011(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H005), C13(H006), C14(H007), C008(H008), C16(H009), C00A(H00A), C00B(H00B),
  C3(H00H), C5(H00J), C00I(H00I), C1(H00N), C6(H00P), C00R(H00R), C00S(H00S),
 C00W(H00W), C010(H010)
2.d Idealised Me refined as rotating group:
 C00H(H00C,H00D,H00E), C17(H00Q,H00T,H00U)
;
_olex2_submission_special_instructions 'No special instructions were received'