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_7717159
_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         '2(C23 H37 N2 O2 P)'
_chemical_formula_sum            'C46 H74 N4 O4 P2'
_chemical_formula_weight         809.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.63150(10)
_cell_length_b                   23.1136(2)
_cell_length_c                   31.6638(3)
_cell_measurement_reflns_used    20434
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.8500
_cell_measurement_theta_min      3.8110
_cell_volume                     9244.55(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.93a 64-bit (release 17-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (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 2014/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.889
_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   -120.00 -35.00   0.50    2.11    --  -47.65 -53.00 137.00  170
  2  \w   -161.00 -77.00   0.50    8.44    --  -90.00 -53.00 137.00  168
  3  \w   -160.00 -83.00   0.50    8.44    --  -90.00-105.00  50.00  154
  4  \w     41.00 107.00   0.50    8.44    --  110.79-105.00  50.00  132
  5  \w     40.00  87.00   0.50    8.44    --  110.79 -73.00 -64.00   94
  6  \w   -120.00 -94.00   0.50    2.11    --  -47.65 -57.00-120.00   52
  7  \w    -32.00  26.00   0.50    2.11    --  -47.65  19.00  60.00  116
  8  \w     94.00 119.00   0.50    2.11    --   47.65  57.00-120.00   50
  9  \w   -156.00-116.00   0.50    8.44    --  -90.00 -99.00-150.00   80
 10  \w   -156.00-125.00   0.50    8.44    --  -90.00 -99.00  30.00   62
 11  \w   -157.00-103.00   0.50    8.44    --  -90.00 -99.00  60.00  108
 12  \w    -65.00 -22.00   0.50    8.44    --  -90.00  57.00 120.00   86
 13  \w     49.00  86.00   0.50    8.44    --  110.79-125.00 -30.00   74
 14  \w     66.00  97.00   0.50    8.44    --  110.79 -77.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0632373000
_diffrn_orient_matrix_UB_12      -0.0131989000
_diffrn_orient_matrix_UB_13      -0.0404424000
_diffrn_orient_matrix_UB_21      0.0436956000
_diffrn_orient_matrix_UB_22      0.0622561000
_diffrn_orient_matrix_UB_23      0.0000559000
_diffrn_orient_matrix_UB_31      0.0946616000
_diffrn_orient_matrix_UB_32      -0.0197527000
_diffrn_orient_matrix_UB_33      0.0270884000
_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  0.0393
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            45381
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.582
_diffrn_reflns_theta_min         3.825
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (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    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             3520
_exptl_crystal_preparation       'Slow evaporation of hexane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         8841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+3.0913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7528
_reflns_number_total             8841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_108_l_new_gaussian
_cod_database_code               7717159
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C23 H37 N2 O2 P1'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.746
_reflns_odcompleteness_completeness 96.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C122(H12D,H12E)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C103(H103), C105(H105)
1.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11S,H11T,H11U),
 C12(H12I,H12J,H12K), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C),
 C107(H10D,H10E,H10F), C108(H10A,H10B,H10C), C109(H10G,H10H,H10I), C111(H11D,
 H11E,H11F), C112(H11P,H11Q,H11R), C113(H11M,H11N,H11O), C115(H11A,H11B,H11C),
 C116(H11J,H11K,H11L), C117(H11G,H11H,H11I), C121(H12A,H12B,H12C), C123(H12F,
 H12G,H12H)
;
_shelx_res_checksum              50240
_shelx_hkl_checksum              52547
_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 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.677