Accessing five- and seven-membered phosphorus-based heterocycles <i>via</i> cycloaddition reactions of azophosphines.
Calder, Ethan D. E.; Male, Louise; Jupp, Andrew R.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 15032–15039; doi:10.1039/d4dt02248c

data_7717161
_publ_section_title
;
 Accessing five- and seven-membered phosphorus-based heterocycles
 <i>via</i> cycloaddition reactions of azophosphines.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15032
_journal_page_last               15039
_journal_paper_doi               10.1039/d4dt02248c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C51 H49 B F15 N2 O8 P, 0.5(C6 H14)'
_chemical_formula_sum            'C54 H56 B F15 N2 O8 P'
_chemical_formula_weight         1187.78
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4583(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   45.26149(17)
_cell_length_b                   14.39164(5)
_cell_length_c                   18.01887(8)
_cell_measurement_reflns_used    119610
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      31.201022395617183
_cell_measurement_theta_min      0.8823401009398892
_cell_volume                     11503.33(8)
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction
;
DIALS 3.12.1-2-g1c07bc2b3-release (Winter, G. et al., 2018)
dials.scale (Beilsten-Edmands, J. et al., 2020)
XIA2 3.12.0 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            348690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         28.581
_diffrn_reflns_theta_min         1.118
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9951097629907026
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
DIALS 3.12.1-2-g1c07bc2b3-release
Scaling & analysis of unmerged intensities, 
absorption correction using spherical harmonics
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             4904
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1506
_refine_ls_number_reflns         32216
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0939P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19962
_reflns_number_total             32216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_141_a
_cod_database_code               7717161
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.84012
 0.15988
2. Restrained distances
 C201-C202 = C202-C203 = C203-C204 = C204-C205 = C205-C26A
 1.52 with sigma of 0.02
 C21A-C202 = C206-C205
 1.52 with sigma of 0.02
 C202-C204 = C203-C205
 2.54 with sigma of 0.04
 C201-C203 = C204-C26A = C204-C206 = C21A-C203
 2.53 with sigma of 0.04
3. Rigid bond restraints
 C21A, C26A, C201, C202, C203, C204, C205, C206
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C32, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C21A \\sim C26A \\sim C201 \\sim C202 \\sim C203 \\sim C204 \\sim C205 \\sim
C206: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
5. Others
 Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(H20F)=Sof(H20G)=1-FVAR(1)
 Sof(C201)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(H20D)=Sof(H20E)=FVAR(1)
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(H20N)=Sof(H20O)=1-FVAR(2)
 Sof(H20L)=Sof(H20M)=Sof(C206)=Sof(H20P)=Sof(H20Q)=Sof(H20R)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C24(H24A,H24B), C30(H30A,H30B), C32(H32A,H32B), C122(H12D,
 H12E), C124(H12I,H12J), C130(H13D,H13E), C132(H13I,H13J), C202(H20F,H20G),
 C202(H20D,H20E), C203(H20H,H20I), C204(H20J,H20K), C205(H20N,H20O), C205(H20L,
 H20M)
6.b Me refined with riding coordinates:
 C21A(H21A,H21B,H21C), C26A(H26A,H26B,H26C), C201(H20A,H20B,H20C), C206(H20P,
 H20Q,H20R)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C103(H103), C105(H105)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C31(H31A,
 H31B,H31C), C33(H33A,H33B,H33C), C107(H10A,H10B,H10C), C108(H10D,H10E,H10F),
 C109(H10G,H10H,H10I), C111(H11D,H11E,H11F), C112(H11G,H11H,H11I), C113(H11J,
 H11K,H11L), C115(H11M,H11N,H11O), C116(H11P,H11Q,H11R), C117(H11S,H11T,H11U),
 C123(H12F,H12G,H12H), C125(H12K,H12L,H12M), C131(H13F,H13G,H13H), C133(H13K,
 H13L,H13M)
;
_shelx_res_checksum              77003
_shelx_hkl_checksum              6339
_olex2_submission_special_instructions 'No special instructions were received'