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_1572036
_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         'C34 H38 N P3'
_chemical_formula_sum            'C34 H38 N P3'
_chemical_formula_weight         553.56
_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             2022-11-28
_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                103.595(2)
_cell_angle_beta                 90.873(2)
_cell_angle_gamma                109.755(2)
_cell_formula_units_Z            4
_cell_length_a                   13.3026(7)
_cell_length_b                   15.2580(8)
_cell_length_c                   16.3831(8)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.31
_cell_volume                     3025.6(3)
_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      273.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.939
_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  0.0682
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52160
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.964
_diffrn_reflns_theta_min         1.467
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7352
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0958 after correction.
The Ratio of minimum to maximum transmission is 0.9066.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       blade
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         13650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0498P)^2^+1.6789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10058
_reflns_number_total             13650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im091
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572036
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C20(H20), C48(H48), C54(H54), C14(H14), C57(H57), C41(H41),
 C4(H4), C45(H45), C37(H37), C7(H7), C11(H11), C29(H29), C38(H38), C5(H5),
 C40(H40), C39(H39), C63(H63), C6(H6), C32(H32), C66(H66)
2.b Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C10(H10A,H10B,
 H10C), C62(H62A,H62B,H62C), C44(H44A,H44B,H44C), C19(H19A,H19B,H19C),
 C01N(H01A,H01B,H01C), C16(H16A,H16B,H16C), C28(H28A,H28B,H28C), C34(H34A,H34B,
 H34C), C53(H53A,H53B,H53C), C59(H59A,H59B,H59C), C47(H47A,H47B,H47C), C13(H13A,
 H13B,H13C), C68(H68A,H68B,H68C), C31(H31A,H31B,H31C), C65(H65A,H65B,H65C)
;
_shelx_res_checksum              34228
_olex2_submission_special_instructions 'No special instructions were received'