Substituent-dependent [4+2] or [2+2] cycloadditions of phenylallenyl phosphine oxides with arynes.
Qin, Yunlong; Zhang, Jianing; Zhang, Congcong; Wang, Qilin; Chemical communications (Cambridge, England) 60 (2024) 11343–11346; doi:10.1039/d4cc03507k

data_7133823
_publ_section_title
;
 Substituent-dependent [4+2] or [2+2] cycloadditions of phenylallenyl
 phosphine oxides with arynes.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11343
_journal_page_last               11346
_journal_paper_doi               10.1039/d4cc03507k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H25 O P'
_chemical_formula_sum            'C26 H25 O P'
_chemical_formula_weight         384.43
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2024-03-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.454(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0883(6)
_cell_length_b                   6.3238(2)
_cell_length_c                   21.6180(8)
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      75.8790
_cell_measurement_theta_min      4.3230
_cell_volume                     2073.83(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    143.00 168.00   0.50    0.30    --  104.75 125.00-180.00   50
  2  \w    132.00 171.00   0.50    0.30    --  104.75 125.00-150.00   78
  3  \w     85.00 117.00   0.50    0.30    --  104.75 125.00-180.00   64
  4  \w     88.00 124.00   0.50    0.30    --  104.75 125.00-150.00   72
  5  \w     44.00 108.00   0.50    0.15    --   47.88  32.00 -39.00  128
  6  \w    100.00 127.00   0.50    0.30    --  104.75 125.00 150.00   54
  7  \w    136.00 165.00   0.50    0.30    --  104.75 125.00 150.00   58
  8  \w     98.00 126.00   0.50    0.30    --  104.75  32.00 -39.00   56
  9  \w     33.00  68.00   0.50    0.30    --  104.75 -57.00-150.00   70
 10  \w     34.00  67.00   0.50    0.30    --  104.75 -57.00-180.00   66
 11  \w     36.00  67.00   0.50    0.30    --  104.75 -57.00-120.00   62
 12  \w    -12.00  14.00   0.50    0.15    --   47.88 -19.00   0.00   52
 13  \w      6.00  38.00   0.50    0.15    --   47.88 -32.00 160.00   64
 14  \w     34.00  61.00   0.50    0.30    --  104.75 -57.00 150.00   54
 15  \w     34.00  59.00   0.50    0.30    --  104.75 -57.00 -60.00   50
 16  \w     36.00  85.00   0.50    0.30    --  104.75 -99.00 -60.00   98
 17  \w    -33.00  25.00   0.50    0.15    --  -47.88  32.00 -39.00  116
 18  \w     38.00 106.00   0.50    0.30    --  104.75 -99.00-180.00  136
 19  \w    -23.00  24.00   0.50    0.15    --  -47.88  38.00  90.00   94
 20  \w   -117.00 -39.00   0.50    0.15    --  -47.88 -32.00 160.00  156
 21  \w    -64.00 -33.00   0.50    0.30    -- -104.00  57.00  30.00   62
 22  \w    -64.00 -32.00   0.50    0.30    -- -104.00  57.00   0.00   64
 23  \w    -64.00 -32.00   0.50    0.30    -- -104.00  57.00-120.00   64
 24  \w    -62.00 -34.00   0.50    0.30    -- -104.00  57.00  60.00   56
 25  \w    -60.00 -34.00   0.50    0.30    -- -104.00  57.00  90.00   52
 26  \w    -64.00 -38.00   0.50    0.30    -- -104.00  57.00 150.00   52
 27  \w   -174.00 -93.00   0.50    0.30    -- -104.00 -32.00 160.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213091000
_diffrn_orient_matrix_UB_12      0.0506149000
_diffrn_orient_matrix_UB_13      -0.0628191000
_diffrn_orient_matrix_UB_21      -0.0936969000
_diffrn_orient_matrix_UB_22      0.0890878000
_diffrn_orient_matrix_UB_23      -0.0320424000
_diffrn_orient_matrix_UB_31      0.0328728000
_diffrn_orient_matrix_UB_32      0.2209604000
_diffrn_orient_matrix_UB_33      0.0272494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13907
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.767
_diffrn_reflns_theta_min         2.913
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+1.8822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3413
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03507k2.cif
_cod_data_source_block           qyl-39
_cod_database_code               7133823
_shelx_shelxl_version_number     2018/3
_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:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              47690
_shelx_hkl_checksum              65573
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.937
_oxdiff_exptl_absorpt_empirical_full_min 0.670