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_7133822
_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         'C29 H25 O P'
_chemical_formula_sum            'C29 H25 O P'
_chemical_formula_weight         420.46
_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     direct
_audit_creation_date             2024-03-30
_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                 109.7320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.16530(10)
_cell_length_b                   15.5130(2)
_cell_length_c                   13.4254(2)
_cell_measurement_reflns_used    12832
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.5080
_cell_measurement_theta_min      4.4570
_cell_volume                     2188.84(5)
_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_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_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    106.00 143.00   0.50    0.20    --  104.75-169.00 -57.00   74
  2  \w     95.00 120.00   0.50    0.10    --   48.13-169.00 -57.00   50
  3  \w     80.00 174.00   0.50    0.20    --  104.75 125.00-120.00  188
  4  \w     53.00 115.00   0.50    0.10    --   48.13 169.00 -41.00  124
  5  \w     82.00 174.00   0.50    0.20    --  104.75 125.00  30.00  184
  6  \w    -20.00  24.00   0.50    0.10    --   48.13 -19.00   0.00   88
  7  \w     35.00 105.00   0.50    0.20    --  104.75 -99.00  90.00  140
  8  \w     42.00 105.00   0.50    0.20    --  104.75-115.00  85.00  126
  9  \w     25.00  50.00   0.50    0.10    --   48.13-115.00  85.00   50
 10  \w    -25.00  26.00   0.50    0.10    --  -48.13  19.00   0.00  102
 11  \w    -58.00 -33.00   0.50    0.20    -- -104.00  57.00   0.00   50
 12  \w    -77.00 -32.00   0.50    0.20    -- -104.00  77.00 150.00   90
 13  \w    -64.00 -34.00   0.50    0.20    -- -104.00  57.00 150.00   60
 14  \w    -64.00 -37.00   0.50    0.20    -- -104.00  57.00 120.00   54
 15  \w    -64.00 -35.00   0.50    0.20    -- -104.00  57.00 -30.00   58
 16  \w    -64.00 -32.00   0.50    0.20    -- -104.00  57.00 -60.00   64
 17  \w    -41.00  22.00   0.50    0.10    --  -48.13  38.00 -60.00  126
 18  \w    -60.00 -34.00   0.50    0.20    -- -104.00  57.00-150.00   52
 19  \w   -127.00-101.00   0.50    0.20    -- -104.00 -19.00 -90.00   52
 20  \w   -175.00-150.00   0.50    0.20    -- -104.00 -19.00 -90.00   50
 21  \w   -169.00-143.00   0.50    0.20    -- -104.00 -19.00  30.00   52
 22  \w   -168.00 -81.00   0.50    0.20    -- -104.00-115.00  85.00  174
 23  \w   -118.00 -47.00   0.50    0.10    --  -48.13-169.00 -57.00  142
 24  \w    -98.00 -73.00   0.50    0.20    -- -104.00-169.00 -57.00   50
;
_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      -0.0772556000
_diffrn_orient_matrix_UB_12      -0.0630620000
_diffrn_orient_matrix_UB_13      0.0431278000
_diffrn_orient_matrix_UB_21      -0.0845524000
_diffrn_orient_matrix_UB_22      0.0750637000
_diffrn_orient_matrix_UB_23      0.0119135000
_diffrn_orient_matrix_UB_31      -0.0914341000
_diffrn_orient_matrix_UB_32      -0.0160494000
_diffrn_orient_matrix_UB_33      -0.1133729000
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16480
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.430
_diffrn_reflns_theta_min         4.472
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79497
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0310P)^2^+1.3657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4190
_reflns_number_total             4430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03507k2.cif
_cod_data_source_block           qyl-35
_cod_database_code               7133822
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N P'
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              7601
_shelx_hkl_checksum              59800
_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.692