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_7133820
_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         'C27 H20 F O P'
_chemical_formula_sum            'C27 H20 F O P'
_chemical_formula_weight         410.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-01
_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                 91.695(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1019(2)
_cell_length_b                   13.6934(3)
_cell_length_c                   12.1992(2)
_cell_measurement_reflns_used    5058
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4010
_cell_measurement_theta_min      3.6160
_cell_volume                     2020.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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     34.00  61.00   1.00    1.00    --   40.73 -38.00   0.00   27
  2  \w     50.00  75.00   1.00    1.00    --   40.73-125.00 -30.00   25
  3  \w     36.00 113.00   1.00    1.00    --  106.95-125.00-120.00   77
  4  \w     38.00 136.00   1.00    1.00    --  106.95 -61.00   0.00   98
  5  \w    136.00 162.00   1.00    1.00    --  106.95  45.00  30.00   26
  6  \w    113.00 166.00   1.00    1.00    --  106.95 125.00  60.00   53
  7  \w    146.00 171.00   1.00    1.00    --  106.95 125.00  30.00   25
  8  \w    109.00 162.00   1.00    1.00    --  106.95 125.00 120.00   53
  9  \w     99.00 134.00   1.00    1.00    --  106.95 125.00  30.00   35
 10  \w     80.00 146.00   1.00    1.00    --  106.95  30.00-180.00   66
 11  \w   -112.00 -19.00   1.00    1.00    --  -40.73 -38.00-150.00   93
 12  \w   -112.00 -17.00   1.00    1.00    --  -40.73 -38.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0396823000
_diffrn_orient_matrix_UB_12      -0.0119335000
_diffrn_orient_matrix_UB_13      -0.1204579000
_diffrn_orient_matrix_UB_21      -0.0590981000
_diffrn_orient_matrix_UB_22      0.0993944000
_diffrn_orient_matrix_UB_23      0.0050486000
_diffrn_orient_matrix_UB_31      0.1055946000
_diffrn_orient_matrix_UB_32      0.0512737000
_diffrn_orient_matrix_UB_33      -0.0378952000
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.533
_diffrn_reflns_theta_min         4.856
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0904P)^2^+0.4154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3590
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03507k2.cif
_cod_data_source_block           27-sd
_cod_database_code               7133820
_shelx_shelxl_version_number     2018/3
_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
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              96771
_shelx_hkl_checksum              82884
_olex2_date_sample_data_collection 2024-02-01
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.326
_oxdiff_exptl_absorpt_empirical_full_min 0.484