[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_1567696
_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         'C34 H26 O2'
_chemical_formula_sum            'C34 H26 O2'
_chemical_formula_weight         466.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-27 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2899(2)
_cell_length_b                   10.6993(2)
_cell_length_c                   13.1402(3)
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      21.77
_cell_measurement_theta_min      2.39
_cell_volume                     1248.51(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            52824
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.744
_diffrn_reflns_theta_min         2.293
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1215 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9491. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         7737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.2158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5613
_reflns_number_total             7737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03073j2.cif
_cod_data_source_block           so2006
_cod_depositor_comments
'Adding full bibliography for 1567695--1567699.cif.'
_cod_database_code               1567696
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C28(H28), C5(H5), C14(H14), C18(H18), C4(H4), C22(H22),
 C21(H21), C7(H7), C27(H27), C11(H11), C30(H30), C34(H34), C15(H15), C12(H12),
 C24(H24), C26(H26), C33(H33), C25(H25), C31(H31), C32(H32)
;
_shelx_res_checksum              50279
_shelx_hkl_checksum              42212
_olex2_submission_special_instructions 'No special instructions were received'