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_1572038
_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         'C29 H36 N P3'
_chemical_formula_sum            'C29 H36 N P3'
_chemical_formula_weight         491.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-10
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6132(9)
_cell_length_b                   12.7998(7)
_cell_length_c                   26.6995(16)
_cell_measurement_reflns_used    9763
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.19
_cell_volume                     5335.8(5)
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0594
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            75209
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_min         1.525
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0562 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.9202.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 4344 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         12747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0367P)^2^+2.6858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                10377
_reflns_number_total             12747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im080
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572038
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.940
_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:
 C00D(H00D), C00M(H00M), C00Q(H00Q), C00X(H00X), C010(H010), C012(H012),
 C016(H016), C01A(H01A), C01E(H4), C01G(H6), C01H(H01H), C01K(H7)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00Y(H00E,H00F,H00G), C00Z(H00H,H00I,H00J), C014(H01,H,
 HA), C015(H1,HB,HC), C018(H2,HD,HE), C01D(H3,HF,HG), C01F(H5,HH,HI), C01I(H01B,
 H01C,H01D), C01J(H01E,H01F,H01G), C01L(H8,HJ,HK), C01M(H01I,H01J,H01K),
 C01N(H01L,H01M,H01N), C01O(H9,HL,HM), C01P(H01O,H01P,H01Q), C01Q(H01R,H01S,
 H01T), C01R(H10,HN,HO), C01S(H01U,H01V,H01W), C01T(H01X,H01Y,HP), C01U(H01Z,HQ,
 HR)
;
_shelx_res_checksum              89943
_olex2_submission_special_instructions 'No special instructions were received'