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_1572030
_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         'C F3 O3 S, C19 H33 N P3, 0.5[]'
_chemical_formula_sum            'C20 H33 F3 N O3 P3 S'
_chemical_formula_weight         517.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.586(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5059(5)
_cell_length_b                   14.4773(8)
_cell_length_c                   21.4699(12)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      3.18
_cell_volume                     2953.6(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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 0.996
_diffrn_measured_fraction_theta_max 0.983
_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  0.045
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            48692
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.512
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0704 before and 0.0303 after correction.
 
For component 2:
 wR2(int) was 0.1677 before and 0.0546 after correction.
 The Ratio of minimum to maximum transmission is 0.67.

Final HKLF 4 output contains 48438 reflections, Rint = 0.0445
 (18009 with I > 3sig(I), Rint = 0.0393)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         8885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0686P)^2^+0.2493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7229
_reflns_number_total             8885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im027_sq
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572030
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.884
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              51737
_shelx_fab_checksum              11318
_platon_squeeze_void_probe_radius 1.20
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in oil'
_olex2_submission_original_sample_id '200703 EL2'
_olex2_submission_special_instructions 'No special instructions were received'