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_7717155
_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         'C23 H35 N2 O4 P'
_chemical_formula_sum            'C23 H35 N2 O4 P'
_chemical_formula_weight         434.50
_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             2024-05-01
_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                90
_cell_angle_beta                 96.910(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0832(4)
_cell_length_b                   9.8167(2)
_cell_length_c                   28.9289(6)
_cell_measurement_reflns_used    14342
_cell_measurement_temperature    99.96(14)
_cell_measurement_theta_max      72.7750
_cell_measurement_theta_min      3.6930
_cell_volume                     4816.16(18)
_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 (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      99.96(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -64.00  31.00   1.00    5.13    --  -41.81  38.00-120.00   95
  2  \w   -120.00  -5.00   1.00    5.13    --  -41.81 -19.00  60.00  115
  3  \w     27.00  95.00   1.00    5.13    --   41.81-125.00   0.00   68
  4  \w     33.00 130.00   1.00   20.50    --  102.88 -61.00  30.00   97
  5  \w     79.00 174.00   1.00   20.50    --  102.88  45.00 120.00   95
  6  \w    104.00 175.00   1.00   20.50    --  102.88 111.00  30.00   71
  7  \w     61.00 146.00   1.00   20.50    --  102.88 178.00 -30.00   85
  8  \w    103.00 177.00   1.00   20.50    --  102.88  77.00-180.00   74
  9  \w    104.00 175.00   1.00   20.50    --  102.88 111.00  60.00   71
 10  \w    103.00 177.00   1.00   20.50    --  102.88  77.00 150.00   74
 11  \w     31.00 108.00   1.00   20.50    --  102.88-111.00   0.00   77
 12  \w     15.00 112.00   1.00    5.13    --   41.81  57.00 -90.00   97
 13  \w     15.00 112.00   1.00    5.13    --   41.81  57.00-180.00   97
 14  \w     15.00 112.00   1.00    5.13    --   41.81  57.00   0.00   97
 15  \w     57.00 122.00   1.00   20.50    --  102.88  15.00 -30.00   65
;
_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      0.0825975000
_diffrn_orient_matrix_UB_12      0.0273313000
_diffrn_orient_matrix_UB_13      -0.0143695000
_diffrn_orient_matrix_UB_21      0.0267399000
_diffrn_orient_matrix_UB_22      0.0593012000
_diffrn_orient_matrix_UB_23      0.0486807000
_diffrn_orient_matrix_UB_31      0.0267737000
_diffrn_orient_matrix_UB_32      -0.1425782000
_diffrn_orient_matrix_UB_33      0.0174306000
_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  0.0435
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            36542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.009
_diffrn_reflns_theta_min         3.787
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             1872
_exptl_crystal_preparation       'Slow evaporation of hexane'
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0569P)^2^+0.6224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7213
_reflns_number_total             9464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_098_f_gaussian
_cod_database_code               7717155
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C23 H35 O4 N2 P1'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C21(H21), C18(H18), C121(H121), C118(H118)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C114(H11D,H11E), C116(H11I,H11J)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C103(H103), C105(H105)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C23(H23A,H23B,H23C),
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C107(H10A,H10B,H10C), C108(H10D,H10E,H10F),
 C109(H10G,H10H,H10I), C122(H12A,H12B,H12C), C123(H12D,H12E,H12F), C120(H12G,
 H12H,H12I), C119(H11A,H11B,H11C), C115(H11F,H11G,H11H), C117(H11K,H11L,H11M)
;
_shelx_res_checksum              18477
_shelx_hkl_checksum              61182
_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 1.536
_oxdiff_exptl_absorpt_empirical_full_min 0.823