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_7133819
_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 Br O P'
_chemical_formula_sum            'C27 H20 Br O P'
_chemical_formula_weight         471.31
_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             2023-07-06
_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                 102.601(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9801(3)
_cell_length_b                   17.8286(8)
_cell_length_c                   15.0481(7)
_cell_measurement_reflns_used    4888
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2750
_cell_measurement_theta_min      2.9620
_cell_volume                     2089.38(16)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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    -48.00  20.00   1.00    1.00    --  -40.73  77.00  90.00   68
  2  \w   -113.00 -14.00   1.00    1.00    --  -40.73 -57.00-180.00   99
  3  \w     38.00  83.00   1.00    1.00    --   40.73-125.00-150.00   45
  4  \w     57.00 132.00   1.00    1.35    --  106.95 -45.00-150.00   75
  5  \w     91.00 129.00   1.00    1.35    --  106.95 -77.00-150.00   38
  6  \w     81.00 171.00   1.00    1.35    --  106.95  30.00  30.00   90
  7  \w    115.00 178.00   1.00    1.35    --  106.95 125.00   0.00   63
  8  \w    102.00 175.00   1.00    1.35    --  106.95 125.00-150.00   73
  9  \w     50.00  87.00   1.00    1.35    --  106.95 -61.00  90.00   37
 10  \w     77.00 107.00   1.00    1.35    --  106.95 -95.00 120.00   30
 11  \w     28.00  56.00   1.00    1.35    --  106.95 -95.00 120.00   28
;
_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      0.0535037000
_diffrn_orient_matrix_UB_12      -0.0779770000
_diffrn_orient_matrix_UB_13      0.0404696000
_diffrn_orient_matrix_UB_21      0.0693662000
_diffrn_orient_matrix_UB_22      0.0361742000
_diffrn_orient_matrix_UB_23      0.0940572000
_diffrn_orient_matrix_UB_31      -0.1769866000
_diffrn_orient_matrix_UB_32      -0.0093544000
_diffrn_orient_matrix_UB_33      0.0234100000
_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  0.0366
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7911
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.613
_diffrn_reflns_theta_min         3.900
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37665
_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            'light colourless'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0806P)^2^+0.6016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3570
_reflns_number_total             4099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03507k2.cif
_cod_data_source_block           qyl-a
_cod_database_code               7133819
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              50568
_shelx_hkl_checksum              63832
_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 2.088
_oxdiff_exptl_absorpt_empirical_full_min 0.604