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_1572037
_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         'C54 H66 P6, C4 H10 O'
_chemical_formula_sum            'C58 H76 O P6'
_chemical_formula_weight         975.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-23
_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                 97.626(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.273(4)
_cell_length_b                   8.550(3)
_cell_length_c                   24.630(8)
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.38
_cell_volume                     2770.4(16)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker-Nonius Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_min         1.668
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1303 before and 0.0843 after correction.
The ratio of minimum to maximum transmission is 0.7432.
The \l/2 correction factor is not present.
;
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1044
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Et2O and pentane  by slow evaporation'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0694
_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^)+(0.1421P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             5012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im090
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_original_cell_volume        2770.3(15)
_cod_database_code               1572037
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Restrained distances
 C17-C13 \\sim C34-C17A \\sim C18-C15 \\sim C36-C18A
 with sigma of 0.02
 C16-C11 \\sim C17-C13 \\sim C18-C15
 with sigma of 0.01
 C16-C11 \\sim C32-C16A \\sim C34-C17A \\sim C17-C13 \\sim C36-C18A \\sim
C18-C15
 with sigma of 0.01
2. Rigid body (RIGU) restrains
 C10, C11, C12, C13, C14, C15, C16, C17, C18, C31, C32, C33, C34, C35, C36,
 C17A, C18A, C16A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C31)=Sof(C32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(C35)=Sof(H35)=Sof(C36)=
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=
 Sof(H18F)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C14(H14), C21(H21), C23(H23), C33(H33), C35(H35)
4.c Fitted hexagon refined as free rotating group:
 C10(C11,C12,C13,C14,C15), C31(C32,C33,C34,C35,C36)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C17A(H17D,H17E,H17F),
 C18A(H18D,H18E,H18F), C16A(H16D,H16E,H16F)
;
_shelx_res_checksum              25840
_olex2_diffrn_ambient_temperature_device Kryoflex
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_original_sample_id P6Mes6.Et2O
_olex2_submission_special_instructions 'No special instructions were received'