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_7717154
_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         'C25 H39 N2 O4 P'
_chemical_formula_sum            'C25 H39 N2 O4 P'
_chemical_formula_weight         462.55
_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             2024-05-01
_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                94.526(3)
_cell_angle_beta                 97.708(3)
_cell_angle_gamma                103.731(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0234(3)
_cell_length_b                   8.2718(3)
_cell_length_c                   19.6948(7)
_cell_measurement_reflns_used    7075
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.7820
_cell_measurement_theta_min      4.5030
_cell_volume                     1249.92(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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   -116.00 -17.00   1.00    5.87    --  -41.27 -38.00-150.00   99
  2  \w    -66.00  33.00   1.00    5.87    --  -41.27  38.00  30.00   99
  3  \w    -87.00  -6.00   1.00    5.87    --  -41.27 125.00  90.00   81
  4  \w    -21.00  74.00   1.00    5.87    --   41.27 -77.00  60.00   95
  5  \w      6.00  82.00   1.00    5.87    --   41.27 -99.00  90.00   76
  6  \w     61.00 146.00   1.00   23.49    --  103.11 178.00 120.00   85
  7  \w     61.00 146.00   1.00   23.49    --  103.11 178.00-180.00   85
  8  \w     30.00 129.00   1.00   23.49    --  103.11 -45.00-120.00   99
  9  \w     75.00 178.00   1.00   23.49    --  103.11  30.00-150.00  103
 10  \w     27.00 109.00   1.00   23.49    --  103.11-111.00 -90.00   82
 11  \w     27.00 109.00   1.00   23.49    --  103.11-111.00-180.00   82
 12  \w    103.00 178.00   1.00   23.49    --  103.11  77.00 -30.00   75
 13  \w     61.00 146.00   1.00   23.49    --  103.11 178.00  60.00   85
 14  \w     27.00 109.00   1.00   23.49    --  103.11-111.00 120.00   82
 15  \w     75.00 178.00   1.00   23.49    --  103.11  30.00 -60.00  103
 16  \w     30.00 129.00   1.00   23.49    --  103.11 -45.00   0.00   99
 17  \w     30.00 129.00   1.00   23.49    --  103.11 -45.00 120.00   99
 18  \w   -113.00 -13.00   1.00    5.87    --  -41.27 -57.00 120.00  100
 19  \w   -113.00 -25.00   1.00    5.87    --  -41.27 -57.00 -60.00   88
 20  \w   -113.00 -13.00   1.00    5.87    --  -41.27 -57.00  30.00  100
;
_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      0.0196472000
_diffrn_orient_matrix_UB_12      0.0907074000
_diffrn_orient_matrix_UB_13      0.0731063000
_diffrn_orient_matrix_UB_21      -0.0064779000
_diffrn_orient_matrix_UB_22      0.1642819000
_diffrn_orient_matrix_UB_23      -0.0308304000
_diffrn_orient_matrix_UB_31      -0.1990949000
_diffrn_orient_matrix_UB_32      -0.0450959000
_diffrn_orient_matrix_UB_33      -0.0043932000
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.838
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0425P)^2^+0.6227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4027
_reflns_number_total             4852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_076_7b_gaussian
_cod_database_code               7717154
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C25 H39 O4 N2 P1'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
1.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C19(H19A,H19B,H19C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C23(H23A,H23B,
 H23C), C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              16538
_shelx_hkl_checksum              86371
_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.495