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_1572033
_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 H39 N1 P3, C O3 F3 S [+solvent]'
_chemical_formula_sum            'C35 H39 F3 N O3 P3 S'
_chemical_formula_weight         703.64
_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   mixed
_audit_creation_date             2022-05-23
_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                113.278(6)
_cell_angle_beta                 98.207(7)
_cell_angle_gamma                93.456(7)
_cell_formula_units_Z            2
_cell_length_a                   11.005(2)
_cell_length_b                   12.506(2)
_cell_length_c                   15.198(3)
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.43
_cell_volume                     1886.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0667
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.956
_diffrn_reflns_theta_min         1.787
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         9011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.8735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6015
_reflns_number_total             9011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im026_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_hydrogen_treatment' value 'Mixed' was changed
to 'mixed' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572027--1572043.cif.
;
_cod_original_cell_volume        1886.1(6)
_cod_database_code               1572033
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C7(H7), C19(H19), C5(H5), C3(H3), C30(H30), C6(H6), C10(H10),
 C28(H28), C4(H4), C12(H12)
1.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C34(H34A,H34B,H34C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C24(H24A,H24B,H24C), C15(H15A,
 H15B,H15C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              64690
_shelx_fab_checksum              97141
_olex2_submission_special_instructions 'No special instructions were received'