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_7133821
_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         'C H Cl3, C F3 O3 S, C21 H26 O P'
_chemical_formula_sum            'C23 H27 Cl3 F3 O4 P S'
_chemical_formula_weight         593.82
_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             2024-02-22
_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                 106.861(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2309(2)
_cell_length_b                   22.3914(4)
_cell_length_c                   12.3597(2)
_cell_measurement_reflns_used    6648
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      3.9210
_cell_volume                     2709.69(9)
_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    'SHELXS  (Sheldrick, 2008)'
_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 0.976
_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     14.00  72.00   1.00    1.00    --   40.73  57.00 -90.00   58
  2  \w     93.00 173.00   1.00    1.40    --  107.58  45.00 -60.00   80
  3  \w    147.00 178.00   1.00    1.40    --  107.58 125.00  90.00   31
  4  \w    115.00 150.00   1.00    1.40    --  107.58 125.00 120.00   35
  5  \w     94.00 172.00   1.00    1.40    --  107.58 125.00   0.00   78
  6  \w     79.00 174.00   1.00    1.40    --  107.58  61.00-180.00   95
  7  \w     35.00  88.00   1.00    1.40    --  107.58 -94.00  60.00   53
  8  \w     32.00 109.00   1.00    1.40    --  107.58 -94.00 120.00   77
  9  \w      2.00  54.00   1.00    1.00    --   40.73 -99.00 -30.00   52
 10  \w     25.00  78.00   1.00    1.00    --   40.73-125.00-180.00   53
 11  \w    -65.00  32.00   1.00    1.00    --  -40.73  38.00  60.00   97
;
_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      0.0841024000
_diffrn_orient_matrix_UB_12      0.0529614000
_diffrn_orient_matrix_UB_13      -0.0235293000
_diffrn_orient_matrix_UB_21      0.0688442000
_diffrn_orient_matrix_UB_22      -0.0417351000
_diffrn_orient_matrix_UB_23      -0.0661784000
_diffrn_orient_matrix_UB_31      -0.1136880000
_diffrn_orient_matrix_UB_32      0.0138454000
_diffrn_orient_matrix_UB_33      -0.1096393000
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11093
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         3.948
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14245
_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    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1173P)^2^+1.8356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4715
_reflns_number_total             5355
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03507k2.cif
_cod_data_source_block           26-xd
_cod_database_code               7133821
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.598
_shelx_estimated_absorpt_t_min   0.534
_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. Rigid bond restraints
 O1, C7
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
3. Uiso/Uaniso restraints and constraints
O1 \\sim C7: within 2A with sigma of 0.0003 and sigma for terminal atoms of
0.0006 within 2A
4.a Ternary CH refined with riding coordinates:
 C23(H23), C16(H16), C19(H19)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              15397
_shelx_hkl_checksum              19623
_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 3.502
_oxdiff_exptl_absorpt_empirical_full_min 0.615