[2 + 2] Cycloaddition of phosphaalkenes as a key step for the reductive coupling of diaryl ketones to tetraaryl olefins
Arkhypchuk, Anna I.; D'Imperio, Nicolas; Wells, Jordann A. L.; Ott, Sascha; Chemical Science 13 (2022) 12239–12244; doi:10.1039/D2SC03073J

data_1567697
_publ_section_title
;
 [2 + 2] Cycloaddition of phosphaalkenes as a key step for the reductive
 coupling of diaryl ketones to tetraaryl olefins
;
_journal_issue                   41
_journal_name_full               'Chemical Science'
_journal_page_first              12239
_journal_page_last               12244
_journal_paper_doi               10.1039/D2SC03073J
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C36 H36 F2 O2'
_chemical_formula_sum            'C36 H36 F2 O2'
_chemical_formula_weight         538.65
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-04-17 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.010(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.356(3)
_cell_length_b                   31.286(8)
_cell_length_c                   9.517(2)
_cell_measurement_reflns_used    8055
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.17
_cell_volume                     2932.4(13)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            42869
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.068
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1374 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7267
_refine_ls_number_restraints     176
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0656P)^2^+1.9329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4443
_reflns_number_total             7267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03073j2.cif
_cod_data_source_block           so2008
_cod_depositor_comments
'Adding full bibliography for 1567695--1567699.cif.'
_cod_original_cell_volume        2932.3(12)
_cod_database_code               1567697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Rigid bond restraints
 C10, C11B, C11A, C12A, C12B, C13A, C13B, C14, C15B, C15A, C16B, C16A, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11B \\sim C11A \\sim C12A \\sim C12B \\sim C13A \\sim C13B \\sim C14
\\sim C15B \\sim C15A \\sim C16B \\sim C16A \\sim C17: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Fixed Sof: H10C(0.66) H10D(0.66) H10A(0.34) H10B(0.34) H14C(0.66) H14D(0.66)
 H14A(0.34) H14B(0.34) C11B(0.66) H11A(0.66) H11B(0.66) C16B(0.66) H16A(0.66)
 H16B(0.66) C15B(0.66) H15A(0.66) H15B(0.66) C16A(0.34) H16C(0.34) H16D(0.34)
 C15A(0.34) H15C(0.34) H15D(0.34) H17C(0.66) H17D(0.66) H17A(0.34) H17B(0.34)
 C13B(0.66) H13A(0.66) H13B(0.66) C12B(0.66) H12A(0.66) H12B(0.66) C13A(0.34)
 H13C(0.34) H13D(0.34) C12A(0.34) H12C(0.34) H12D(0.34) C11A(0.34) H11C(0.34)
 H11D(0.34)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C9(H9A,H9B), C10(H10C,H10D), C10(H10A,H10B), C14(H14C,H14D),
 C14(H14A,H14B), C11B(H11A,H11B), C16B(H16A,H16B), C15B(H15A,H15B), C16A(H16C,
 H16D), C15A(H15C,H15D), C17(H17C,H17D), C17(H17A,H17B), C13B(H13A,H13B),
 C12B(H12A,H12B), C13A(H13C,H13D), C12A(H12C,H12D), C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C21(H21), C20(H20), C30(H30), C32(H32), C4(H4), C26(H26),
 C36(H36), C8(H8), C33(H33), C5(H5), C7(H7), C35(H35), C27(H27), C29(H29)
;
_shelx_res_checksum              97414
_shelx_hkl_checksum              16509
_olex2_submission_special_instructions 'No special instructions were received'