Synthesis of highly condensed phospholes by Lewis acid-assisted dehydrogenative Mallory reaction under visible light irradiation
Kamiyoshi, Ikki; Kojima, Yuki; Xu, Shibo; Yasui, Kosuke; Nishii, Yuji; Hirano, Koji; Chemical Science  (2024) –; doi:10.1039/D4SC05657D

data_1573168
_publ_section_title
;
 Synthesis of highly condensed phospholes by Lewis acid-assisted
 dehydrogenative Mallory reaction under visible light irradiation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC05657D
_journal_year                    2024
_chemical_formula_moiety         'C34 H21 O P, C6 H6'
_chemical_formula_sum            'C40 H27 O P'
_chemical_formula_weight         554.58
_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     dual
_audit_creation_date             2024-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-16 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.436(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3632(3)
_cell_length_b                   11.8180(5)
_cell_length_c                   28.4133(11)
_cell_measurement_reflns_used    7793
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.0190
_cell_measurement_theta_min      4.0130
_cell_volume                     2784.65(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.933
_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    -68.00 -43.00   0.50   46.23    --  -42.93  -3.00  13.00   50
  2  \w    -19.00 102.00   0.50   46.23    --   42.93   3.00-169.00  242
  3  \w     82.00 107.00   0.50  184.91    --   96.50   3.00-169.00   50
  4  \w     19.00  77.00   0.50  184.91    --   96.50   3.00-169.00  116
  5  \w    127.00 152.00   0.50  184.91    --   96.50  -3.00  13.00   50
  6  \w    -70.00 -45.00   0.50  184.91    -- -108.01   3.00-169.00   50
  7  \w   -171.00 -69.00   0.50  184.91    -- -108.01  -3.00  13.00  204
  8  \w      4.00  30.00   0.50   46.23    --  -42.93  57.00-120.00   52
  9  \w    -93.00 -16.00   0.50   46.23    --  -42.93 125.00 -60.00  154
 10  \w    -65.00   0.00   0.50   46.23    --  -42.93  57.00-120.00  130
 11  \w    -47.00 -22.00   0.50   46.23    --  -42.93   3.00-169.00   50
 12  \w    -37.00   0.00   0.50   46.23    --   42.93 -19.00-180.00   74
 13  \w     22.00  48.00   0.50  184.91    --   96.50 -61.00 -30.00   52
 14  \w     24.00  49.00   0.50  184.91    --   96.50 -61.00-180.00   50
 15  \w     22.00  72.00   0.50  184.91    --   96.50 -77.00 -90.00  100
 16  \w     23.00  49.00   0.50  184.91    --   96.50 -61.00-150.00   52
 17  \w     78.00 138.00   0.50  184.91    --   96.50  45.00 150.00  120
 18  \w    -92.00 -42.00   0.50  184.91    -- -108.01  61.00  60.00  100
 19  \w    -55.00 -29.00   0.50  184.91    -- -108.01  30.00 120.00   52
 20  \w    -75.00 -43.00   0.50  184.91    -- -108.01 125.00 -60.00   64
 21  \w   -112.00 -41.00   0.50  184.91    -- -108.01 125.00-180.00  142
 22  \w    -57.00 -31.00   0.50  184.91    -- -108.01  30.00-180.00   52
 23  \w   -112.00 -80.00   0.50  184.91    -- -108.01 125.00 -60.00   64
 24  \w    -89.00 -39.00   0.50  184.91    -- -108.01  61.00 -30.00  100
 25  \w    -56.00 -31.00   0.50  184.91    -- -108.01  30.00-150.00   50
 26  \w   -111.00 -48.00   0.50  184.91    -- -108.01  77.00 -30.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1056388000
_diffrn_orient_matrix_UB_12      -0.0024013000
_diffrn_orient_matrix_UB_13      0.0405607000
_diffrn_orient_matrix_UB_21      -0.1526604000
_diffrn_orient_matrix_UB_22      0.0066487000
_diffrn_orient_matrix_UB_23      -0.0365834000
_diffrn_orient_matrix_UB_31      -0.0055397000
_diffrn_orient_matrix_UB_32      -0.1301744000
_diffrn_orient_matrix_UB_33      -0.0026878000
_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  0.0895
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17419
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.971
_diffrn_reflns_theta_min         4.056
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.117
_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-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0782
_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^)+(0.0505P)^2^+13.7272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             5426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc05657d2.cif
_cod_data_source_block           3_autored
_cod_database_code               1573168
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C40 P O H27'
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C35(H35), C23(H23), C6(H6), C33(H33), C27(H27), C17(H17), C11(H11),
 C32(H32), C20(H20), C7(H7), C34(H34), C22(H22), C29(H29), C30(H30), C31(H31),
 C19(H19), C10(H10), C28(H28), C18(H18), C9(H9), C40(H40), C38(H38), C37(H37),
 C41(H41), C39(H39), C42(H42)
;
_shelx_res_checksum              31409
_shelx_hkl_checksum              93238
_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 2.417
_oxdiff_exptl_absorpt_empirical_full_min 0.159