Accessing five- and seven-membered phosphorus-based heterocycles <i>via</i> cycloaddition reactions of azophosphines.
Calder, Ethan D. E.; Male, Louise; Jupp, Andrew R.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 15032–15039; doi:10.1039/d4dt02248c

data_7717160
_publ_section_title
;
 Accessing five- and seven-membered phosphorus-based heterocycles
 <i>via</i> cycloaddition reactions of azophosphines.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15032
_journal_page_last               15039
_journal_paper_doi               10.1039/d4dt02248c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C49 H45 B F15 N2 O8 P'
_chemical_formula_sum            'C49 H45 B F15 N2 O8 P'
_chemical_formula_weight         1116.65
_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             2024-05-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                112.034(3)
_cell_angle_beta                 97.787(3)
_cell_angle_gamma                107.389(3)
_cell_formula_units_Z            2
_cell_length_a                   12.6836(4)
_cell_length_b                   14.3392(5)
_cell_length_c                   15.9046(5)
_cell_measurement_reflns_used    14828
_cell_measurement_temperature    119.99(10)
_cell_measurement_theta_max      72.6470
_cell_measurement_theta_min      3.7570
_cell_volume                     2456.51(17)
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -71.00  32.00   1.00    1.00    --  -41.27  67.00  63.00  103
  2  \w   -114.00 -11.00   1.00    1.00    --  -41.27 -67.00 -70.00  103
  3  \w     11.00 114.00   1.00    1.00    --   41.27  67.00  63.00  103
  4  \w    -32.00  71.00   1.00    1.00    --   41.27 -67.00 -70.00  103
  5  \w     30.00 133.00   1.00    2.49    --  102.80 -67.00 -70.00  103
  6  \w     73.00 176.00   1.00    2.49    --  102.80  67.00  63.00  103
  7  \w     17.00 116.00   1.00    1.00    --   41.27  38.00-180.00   99
  8  \w      7.00  33.00   1.00    1.00    --   41.27  84.00 142.70   26
  9  \w    -31.00  69.00   1.00    1.00    --   41.27 -57.00 150.00  100
 10  \w     61.00 146.00   1.00    2.49    --  102.80 178.00-150.00   85
 11  \w     20.00 107.00   1.00    2.49    --  102.80 -94.00  30.00   87
 12  \w     29.00 108.00   1.00    2.49    --  102.80-111.00   0.00   79
 13  \w     29.00 108.00   1.00    2.49    --  102.80-111.00 -90.00   79
 14  \w     76.00 175.00   1.00    2.49    --  102.80  52.00 -64.75   99
 15  \w    104.00 176.00   1.00    2.49    --  102.80 111.00 -30.00   72
 16  \w    104.00 176.00   1.00    2.49    --  102.80 111.00-180.00   72
 17  \w    104.00 176.00   1.00    2.49    --  102.80 111.00-150.00   72
 18  \w     27.00 109.00   1.00    2.49    --  102.80-108.00 177.76   82
 19  \w     29.00 108.00   1.00    2.49    --  102.80-111.00 -60.00   79
 20  \w     77.00 176.00   1.00    2.49    --  102.80  45.00 150.00   99
 21  \w    103.00 178.00   1.00    2.49    --  102.80  77.00   0.00   75
 22  \w    104.00 176.00   1.00    2.49    --  102.80 111.00 -60.00   72
 23  \w      6.00  32.00   1.00    1.00    --   41.27  85.00-122.68   26
 24  \w     13.00 114.00   1.00    1.00    --   41.27  57.00-120.00  101
 25  \w     13.00  70.00   1.00    1.00    --   41.27  57.00  30.00   57
 26  \w      5.00  31.00   1.00    1.00    --   41.27  87.00 -85.86   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0459387000
_diffrn_orient_matrix_UB_12      -0.0514560000
_diffrn_orient_matrix_UB_13      -0.0833409000
_diffrn_orient_matrix_UB_21      0.0615063000
_diffrn_orient_matrix_UB_22      0.1131677000
_diffrn_orient_matrix_UB_23      0.0052253000
_diffrn_orient_matrix_UB_31      0.1080901000
_diffrn_orient_matrix_UB_32      0.0160106000
_diffrn_orient_matrix_UB_33      0.0698162000
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.823
_diffrn_reflns_theta_min         3.579
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_preparation       'Slow evaporation of hexane'
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     696
_refine_ls_number_reflns         9592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0455P)^2^+0.9279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7976
_reflns_number_total             9592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_107_c_120_gaussian
_cod_original_cell_volume        2456.51(15)
_cod_database_code               7717160
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C49 H45 F15 O8 N2 P1 B1'
_shelx_estimated_absorpt_t_max   0.808
_shelx_estimated_absorpt_t_min   0.701
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C29(H29), C26(H26)
1.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C31(H31A,H31B,H31C),
 C30(H30A,H30B,H30C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              30137
_shelx_hkl_checksum              96562
_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 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.881