1,3-Dipolar cyclisation reactions of nitriles with sterically encumbered cyclic triphosphanes: synthesis and electronic structure of phosphorus-rich heterocycles with tunable colour.
Nascimento, Mitchell A.; LaPierre, Etienne A.; Patrick, Brian O.; Watson, Jade E. T.; Watanabe, Lara; Rawson, Jeremy; Hering-Junghans, Christian; Manners, Ian; Chemical science 15 (2024) 12006–12016; doi:10.1039/d4sc02497d

data_1572039
_publ_section_title
;
 1,3-Dipolar cyclisation reactions of nitriles with sterically encumbered
 cyclic triphosphanes: synthesis and electronic structure of
 phosphorus-rich heterocycles with tunable colour.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12006
_journal_page_last               12016
_journal_paper_doi               10.1039/d4sc02497d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C38 H54 N P3'
_chemical_formula_sum            'C38 H54 N P3'
_chemical_formula_weight         617.73
_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             2022-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                80.276(2)
_cell_angle_beta                 79.095(2)
_cell_angle_gamma                63.100(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3450(8)
_cell_length_b                   11.9683(8)
_cell_length_c                   15.3035(10)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.549
_cell_measurement_theta_min      2.243
_cell_volume                     1811.4(2)
_computing_cell_refinement       'SAINT V8.40B (2016)'
_computing_data_reduction        'SAINT V8.40B (2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53484
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.617
_diffrn_reflns_theta_min         1.361
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0446 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9630.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       irregular
_exptl_crystal_F_000             668
_exptl_crystal_recrystallization_method Acetonitrile
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         11113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0363
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8801
_reflns_number_total             11113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im050
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572039
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.952
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C33(H33), C9(H9), C36(H36), C12(H12), C24(H24), C21(H21)
1.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C17(H17), C30(H30), C19(H19), C29(H29), C18(H18), C5(H5), C7(H7),
 C6(H6)
1.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C34(H34A,H34B,H34C), C11(H11A,H11B,H11C), C35(H35A,H35B,
 H35C), C10(H10A,H10B,H10C), C37(H37A,H37B,H37C), C14(H14A,H14B,H14C), C38(H38A,
 H38B,H38C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C),
 C13(H13A,H13B,H13C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              96431
_olex2_submission_original_sample_id MAN241
_olex2_submission_special_instructions 'No special instructions were received'