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_7129836
_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         'C30 H31 N O4'
_chemical_formula_sum            'C30 H31 N O4'
_chemical_formula_weight         469.56
_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                98.223(2)
_cell_angle_beta                 92.734(2)
_cell_angle_gamma                119.2730(10)
_cell_formula_units_Z            4
_cell_length_a                   11.4176(5)
_cell_length_b                   11.6040(5)
_cell_length_c                   22.5633(10)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.82
_cell_measurement_theta_min      2.40
_cell_volume                     2556.8(2)
_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  0.0882
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            79310
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.9249.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         9018
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                5475
_reflns_number_total             9018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01324j2.cif
_cod_data_source_block           sust_3232_0m_a
_cod_depositor_comments
'Adding full bibliography for 7129831--7129837.cif.'
_cod_original_cell_volume        2556.78(19)
_cod_database_code               7129836
_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, All O(H) groups
2. Restrained distances
 H5-H59c
 2.45 with sigma of 0.02
 H1-H37a
 2.45 with sigma of 0.02
 H1-H40c
 2.2 with sigma of 0.02
 H5-H58a
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O8) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C20(H20), C23(H23), C26(H26), C30(H30), C34(H34),
 C39(H39), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49),
  C50(H50), C51(H51)
4.b Idealised Me refined as rotating group:
 C36(H36a,H36b,H36c), C37(H37a,H37b,H37c), C40(H40a,H40b,H40c), C43(H43a,H43b,
 H43c), C48(H48a,H48b,H48c), C52(H52a,H52b,H52c), C53(H53a,H53b,H53c), C54(H54a,
 H54b,H54c), C55(H55a,H55b,H55c), C56(H56a,H56b,H56c), C57(H57a,H57b,H57c),
 C58(H58a,H58b,H58c), C59(H59a,H59b,H59c), C60(H60a,H60b,H60c)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'