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_7717157
_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         'C37 H53 N2 O8 P'
_chemical_formula_sum            'C37 H53 N2 O8 P'
_chemical_formula_weight         684.78
_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                110.174(3)
_cell_angle_beta                 93.849(3)
_cell_angle_gamma                98.359(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0797(3)
_cell_length_b                   12.5123(4)
_cell_length_c                   13.9655(5)
_cell_measurement_reflns_used    15826
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      72.6790
_cell_measurement_theta_min      3.7510
_cell_volume                     1783.60(11)
_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      99.98(13)
_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 0.986
_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    -69.00  32.00   1.00    3.41    --  -41.27  57.00 150.00  101
  2  \w    -87.00  -6.00   1.00    3.41    --  -41.27 125.00-150.00   81
  3  \w   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00   0.00  100
  4  \w   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00-120.00  100
  5  \w     29.00 108.00   1.00   13.64    --  102.80-111.00  60.00   79
  6  \w     31.00 132.00   1.00   13.64    --  102.80 -61.00 -60.00  101
  7  \w     31.00 132.00   1.00   13.64    --  102.80 -61.00 150.00  101
  8  \w    104.00 176.00   1.00   13.64    --  102.80 111.00-150.00   72
  9  \w     27.00 131.00   1.00   13.64    --  102.80 -30.00  90.00  104
 10  \w    103.00 178.00   1.00   13.64    --  102.80  77.00  60.00   75
 11  \w     29.00 108.00   1.00   13.64    --  102.80-111.00-180.00   79
 12  \w     29.00 108.00   1.00   13.64    --  102.80-111.00 -30.00   79
 13  \w     29.00 108.00   1.00   13.64    --  102.80-111.00 -90.00   79
 14  \w    103.00 178.00   1.00   13.64    --  102.80  77.00 -90.00   75
 15  \w     50.00 178.00   1.00   13.64    --  102.80  15.00  60.00  128
 16  \w    103.00 178.00   1.00   13.64    --  102.80  80.00 110.00   75
 17  \w     29.00 108.00   1.00   13.64    --  102.80-111.00 150.00   79
 18  \w   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00  60.00  100
 19  \w   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00 120.00  100
 20  \w   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00 -60.00  100
 21  \w    -33.00  66.00   1.00    3.41    --   41.27 -38.00 -30.00   99
 22  \w     13.00 114.00   1.00    3.41    --   41.27  57.00 -90.00  101
 23  \w     74.00 175.00   1.00   13.64    --  102.80  61.00 -90.00  101
 24  \w     74.00 175.00   1.00   13.64    --  102.80  61.00 150.00  101
 25  \w     75.00 178.00   1.00   13.64    --  102.80  30.00-150.00  103
 26  \w     77.00 176.00   1.00   13.64    --  102.80  45.00-120.00   99
 27  \w     74.00 175.00   1.00   13.64    --  102.80  61.00  60.00  101
 28  \w     74.00 175.00   1.00   13.64    --  102.80  61.00 -60.00  101
 29  \w     74.00 175.00   1.00   13.64    --  102.80  61.00  90.00  101
 30  \w     74.00 171.00   1.00   13.64    --  102.80  61.00  30.00   97
 31  \w     74.00 175.00   1.00   13.64    --  102.80  61.00 120.00  101
;
_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      0.1254232000
_diffrn_orient_matrix_UB_12      0.0309494000
_diffrn_orient_matrix_UB_13      0.0668839000
_diffrn_orient_matrix_UB_21      -0.0593259000
_diffrn_orient_matrix_UB_22      -0.0497010000
_diffrn_orient_matrix_UB_23      0.0759442000
_diffrn_orient_matrix_UB_31      0.0286375000
_diffrn_orient_matrix_UB_32      -0.1198059000
_diffrn_orient_matrix_UB_33      -0.0615971000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33249
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.745
_diffrn_reflns_theta_min         3.826
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.823
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       'Slow evaporation of hexane'
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         7013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0405P)^2^+0.8367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5955
_reflns_number_total             7013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_098_c_gaussian
_cod_original_cell_volume        1783.60(10)
_cod_database_code               7717157
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.831
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C26(H26), C32(H32)
1.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C30(H30A,H30B), C29(H29A,H29B), C28(H28A,H28B), C27(H27A,
 H27B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C37(H37A,H37B), 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), C19(H19A,H19B,H19C),
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              42853
_shelx_hkl_checksum              61197
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.734