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_7717156
_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         'C31 H45 N2 O8 P'
_chemical_formula_sum            'C31 H45 N2 O8 P'
_chemical_formula_weight         604.66
_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             2024-05-03
_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                90
_cell_angle_beta                 95.755(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6739(3)
_cell_length_b                   12.9998(2)
_cell_length_c                   14.7844(3)
_cell_measurement_reflns_used    13742
_cell_measurement_temperature    99.96(13)
_cell_measurement_theta_max      72.9640
_cell_measurement_theta_min      4.2600
_cell_volume                     3188.48(10)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(13)
_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 0.985
_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    -66.00  33.00   1.00    1.00    --  -41.27  38.00-120.00   99
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.27 -38.00 -60.00   99
  3  \w      6.00  82.00   1.00    1.00    --   41.27 -99.00 -30.00   76
  4  \w     27.00 109.00   1.00    3.81    --  103.11-111.00 -60.00   82
  5  \w     77.00 176.00   1.00    3.81    --  103.11  45.00 150.00   99
  6  \w    104.00 178.00   1.00    3.81    --  103.11 111.00   0.00   74
  7  \w     20.00 107.00   1.00    3.81    --  103.11 -94.00 -30.00   87
  8  \w    103.00 178.00   1.00    3.81    --  103.11  77.00 -30.00   75
  9  \w    104.00 178.00   1.00    3.81    --  103.11 111.00 -90.00   74
 10  \w     31.00 132.00   1.00    3.81    --  103.11 -61.00   0.00  101
 11  \w     13.00 114.00   1.00    1.00    --   41.27  57.00  60.00  101
 12  \w     13.00 114.00   1.00    1.00    --   41.27  57.00 120.00  101
 13  \w     13.00 114.00   1.00    1.00    --   41.27  57.00-120.00  101
 14  \w     74.00 175.00   1.00    3.81    --  103.11  61.00 -60.00  101
 15  \w     77.00 176.00   1.00    3.81    --  103.11  45.00  60.00   99
 16  \w     74.00 163.00   1.00    3.81    --  103.11  61.00  90.00   89
 17  \w     75.00 178.00   1.00    3.81    --  103.11  30.00-120.00  103
;
_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      0.0565558000
_diffrn_orient_matrix_UB_12      -0.0380715000
_diffrn_orient_matrix_UB_13      -0.0691937000
_diffrn_orient_matrix_UB_21      0.0013490000
_diffrn_orient_matrix_UB_22      0.1088324000
_diffrn_orient_matrix_UB_23      -0.0410648000
_diffrn_orient_matrix_UB_31      0.0736700000
_diffrn_orient_matrix_UB_32      0.0272837000
_diffrn_orient_matrix_UB_33      0.0670178000
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30825
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.961
_diffrn_reflns_theta_min         4.321
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.573
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_preparation
'THF layered with hexane at -30 degrees in a nitrogen atmosphere'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0442
_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^)+(0.0393P)^2^+1.4496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5345
_reflns_number_total             6275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_076_1_final_gaussian
_cod_database_code               7717156
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C23 H35 O4 N2 P1'
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.749
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C29(H29), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C30(H30A,H30B,H30C),
 C31(H31A,H31B,H31C), C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              33006
_shelx_hkl_checksum              49642
_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 2.124
_oxdiff_exptl_absorpt_empirical_full_min 0.620