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_1572042
_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         'C52 H74 N P3'
_chemical_formula_sum            'C52 H74 N P3'
_chemical_formula_weight         806.03
_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   mixed
_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                90
_cell_angle_beta                 98.699(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9840(4)
_cell_length_b                   8.7134(3)
_cell_length_c                   42.5367(14)
_cell_measurement_reflns_used    7620
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.62
_cell_measurement_theta_min      3.75
_cell_volume                     4757.0(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1149
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            39675
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        56.054
_diffrn_reflns_theta_max         56.054
_diffrn_reflns_theta_min         2.101
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.390
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0779 after correction.
The Ratio of minimum to maximum transmission is 0.8776.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         6153
_refine_ls_number_restraints     390
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+6.4409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4534
_reflns_number_total             6153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im030_a
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572042
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
2. Others
 Fixed Sof: C18A(0.6667) H18A(0.6667) H18B(0.6667) H18C(0.6667) C18B(0.3333)
 H18D(0.3333) H18E(0.3333) H18F(0.3333) C19A(0.6667) H19A(0.6667) H19B(0.6667)
 H19C(0.6667) C19B(0.3333) H19D(0.3333) H19E(0.3333) H19F(0.3333) C30A(0.6667)
 H30A(0.6667) H30B(0.6667) H30C(0.6667) C30B(0.3333) H30D(0.3333) H30E(0.3333)
 H30F(0.3333)
3.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20), C32(H32), C35(H35), C44(H44), C47(H47), C50(H50)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C25(H25),
 C27(H27), C40(H40), C42(H42)
3.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18A(H18A,H18B,
 H18C), C18B(H18D,H18E,H18F), C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F),
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C30A(H30A,H30B,H30C), C30B(H30D,H30E,
 H30F), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C),
 C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              12943
_olex2_submission_special_instructions 'No special instructions were received'