Transition-metal-free approaches to 2,3-diarylated indenones from 2-alkynylbenzaldehydes and phenols with tunable selectivity.
Yao, Tuanli; Zhao, Shuaijing; Liu, Tao; Wu, Yuting; Ma, Yanhui; Li, Tao; Qin, Xiangyang; Chemical communications (Cambridge, England) 58 (2022) 4592–4595; doi:10.1039/d2cc01324j

data_7129833
_publ_section_title
;
 Transition-metal-free approaches to 2,3-diarylated indenones from
 2-alkynylbenzaldehydes and phenols with tunable selectivity.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4592
_journal_page_last               4595
_journal_paper_doi               10.1039/d2cc01324j
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C32 H33 F O4'
_chemical_formula_sum            'C32 H33 F O4'
_chemical_formula_weight         500.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                83.875(4)
_cell_angle_beta                 77.861(4)
_cell_angle_gamma                68.433(4)
_cell_formula_units_Z            2
_cell_length_a                   10.7537(13)
_cell_length_b                   11.4253(14)
_cell_length_c                   11.8372(15)
_cell_measurement_reflns_used    3910
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.65
_cell_volume                     1321.6(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_av_unetI/netI     0.0742
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39967
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0686 after correction.
The Ratio of minimum to maximum transmission is 0.9355.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                2505
_reflns_number_total             4644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01324j2.cif
_cod_data_source_block           sust_3231_0m_a
_cod_depositor_comments
'Adding full bibliography for 7129831--7129837.cif.'
_cod_database_code               7129833
_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, All O(H) groups
2. Restrained distances
 H1a-H31c
 2.45 with sigma of 0.02
 H1a-H32a
 2.2 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15), C20(H20),
 C24(H24)
3.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C26(H26a,H26b,H26c), C27(H27a,H27b,H27c), C28(H28a,H28b,
 H28c), C30(H30a,H30b,H30c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1a)
;
_olex2_submission_special_instructions 'No special instructions were received'