A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to synthesize diphosphonyl xanthene derivatives.
Fan, Tao; Liu, Yan; Jiang, Caina; Xu, Yanli; Chen, Yanyan; Organic & biomolecular chemistry 19 (2021) 6609–6612; doi:10.1039/d1ob01045j

data_7158171
_publ_section_title
;
 A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy
 phenylacetylenes to synthesize diphosphonyl xanthene derivatives.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6609
_journal_page_last               6612
_journal_paper_doi               10.1039/d1ob01045j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C39 H32 O3 P2'
_chemical_formula_sum            'C39 H32 O3 P2'
_chemical_formula_weight         610.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-21 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                95.672(7)
_cell_angle_beta                 91.026(7)
_cell_angle_gamma                113.558(8)
_cell_formula_units_Z            2
_cell_length_a                   10.8036(9)
_cell_length_b                   11.4967(9)
_cell_length_c                   15.6103(14)
_cell_measurement_reflns_used    4094
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.2840
_cell_measurement_theta_min      2.3680
_cell_volume                     1765.1(3)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -39.00  59.00   1.00    5.00    --  -11.27  57.00  30.00   98
  2  \w     59.00  86.00   1.00    5.00    --   11.90 178.00-120.00   27
  3  \w    -81.00  14.00   1.00    5.00    --  -11.27 -57.00-120.00   95
  4  \w    -77.00  20.00   1.00    5.00    --  -11.27 -77.00 120.00   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      -0.0489421000
_diffrn_orient_matrix_UB_12      -0.0349591000
_diffrn_orient_matrix_UB_13      0.0278559000
_diffrn_orient_matrix_UB_21      -0.0523150000
_diffrn_orient_matrix_UB_22      -0.0000750000
_diffrn_orient_matrix_UB_23      -0.0281444000
_diffrn_orient_matrix_UB_31      -0.0042589000
_diffrn_orient_matrix_UB_32      -0.0580455000
_diffrn_orient_matrix_UB_33      -0.0229173000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12566
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45077
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0787
_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^)+(0.1008P)^2^+1.4600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4305
_reflns_number_total             6213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01045j2.cif
_cod_data_source_block           f-214
_cod_depositor_comments          'Adding full bibliography for 7158171.cif.'
_cod_database_code               7158171
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C11, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C36(H36), C37(H37), C38(H38)
4.c Idealised Me refined as rotating group:
 C01C(H01A,H01B,H01C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49040
_shelx_fab_checksum              95921
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.626