Stannyl phosphaketene as a synthon for phosphorus analogues of β-lactam
Luo, Yong-An; Zhao, Zhao; Chen, Ting; Li, Yanguo; Zhao, Yufen; Stephan, Douglas W.; Wu, Yile; Chemical Communications  (2023) –; doi:10.1039/D3CC03117A

data_7132028
_publ_section_title
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 Stannyl phosphaketene as a synthon for phosphorus analogues of \b-lactam
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03117A
_journal_year                    2023
_chemical_formula_moiety         'C48 H41 B F15 N2 O P Sn, 2(C7 H8), 0.5(C6 H6)'
_chemical_formula_sum            'C65 H60 B F15 N2 O P Sn'
_chemical_formula_weight         1330.62
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
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2023-05-17 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.655(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5036(7)
_cell_length_b                   25.6431(12)
_cell_length_c                   15.6976(7)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      4.42
_cell_volume                     6238.1(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            150341
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.302
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.266
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.8008.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             2708
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     868
_refine_ls_number_reflns         11017
_refine_ls_number_restraints     440
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+5.4126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10618
_reflns_number_total             11017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03117a2.cif
_cod_data_source_block           11
_cod_database_code               7132028
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 C2-C1A
 1.51 with sigma of 0.02
 C1A-C1B = C1A-C1F = C1C-C1D
 1.39 with sigma of 0.02
 C1B-C1C = C1D-C1E = C1E-C1F
 1.38 with sigma of 0.02
 C101-C102 = C101-C100 = C103-C104
 1.39 with sigma of 0.02
 C102-C103 = C104-C105 = C105-C100
 1.38 with sigma of 0.02
 C107-C108 = C110-C111 = C111-C106
 1.37 with sigma of 0.02
 C107-C106
 1.38 with sigma of 0.02
 C108-C109 = C109-C110
 1.36 with sigma of 0.02
 C1A-C1C
 2.42 with sigma of 0.04
 C1B-C1D
 2.39 with sigma of 0.04
 C1A-C1E
 2.41 with sigma of 0.04
 C1C-C1E = C1D-C1F
 2.4 with sigma of 0.04
 C2-C1B = C2-C1F
 2.52 with sigma of 0.04
 C101-C103
 2.42 with sigma of 0.04
 C101-C105
 2.41 with sigma of 0.04
 C102-C104
 2.39 with sigma of 0.04
 C103-C105 = C104-C100
 2.4 with sigma of 0.04
 C107-C109 = C109-C111 = C110-C106
 2.37 with sigma of 0.04
 C107-C111
 2.38 with sigma of 0.04
 C108-C110
 2.36 with sigma of 0.04
 C1A-C1B \\sim C1B-C1C \\sim C1C-C1D \\sim C1D-C1E \\sim C1E-C1F \\sim C1F-C1A
 with sigma of 0.02
 C1A-C1E \\sim C1A-C1C \\sim C1F-C1D \\sim C1B-C1F \\sim C1C-C1E \\sim C1B-C1D
 with sigma of 0.04
 C2-C1F \\sim C2-C1B
 with sigma of 0.04
 C101-C102 \\sim C102-C103 \\sim C103-C104 \\sim C104-C105 \\sim C105-C100
\\sim C100-C101
 with sigma of 0.02
 C101-C105 \\sim C101-C103 \\sim C100-C104 \\sim C102-C100 \\sim C103-C105
\\sim C102-C104
 with sigma of 0.04
 C107-C108 \\sim C108-C109 \\sim C109-C110 \\sim C110-C111 \\sim C111-C106
\\sim C106-C107
 with sigma of 0.02
 C107-C111 \\sim C107-C109 \\sim C111-C109 \\sim C110-C108 \\sim C110-C106
\\sim C106-C108
 with sigma of 0.04
3. Restrained planarity
 C2, C1A, C1B, C1C, C1D, C1E, C1F
 with sigma of 0.1
 C101, C102, C103, C104, C105, C100
 with sigma of 0.1
 C107, C108, C109, C110, C111, C106
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2 \\sim C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C101 \\sim C102 \\sim C103 \\sim C104 \\sim C105 \\sim C100: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C107 \\sim C108 \\sim C109 \\sim C110 \\sim C111 \\sim C106: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C100) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C102) \\sim Ueq,
Uanis(C103) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C105) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C106) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C108) \\sim Ueq,
Uanis(C109) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C111) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C2, C1A, C1B, C1C, C1D, C1E, C1F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C101, C102, C103, C104, C105, C100
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C107, C108, C109, C110, C111, C106
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C101(0.25) H101(0.25) C102(0.25) H102(0.25) C103(0.25) H103(0.25)
 C104(0.25) H104(0.25) C105(0.25) H105(0.25) C100(0.25) H100(0.25) C107(0.25)
 H107(0.25) C108(0.25) H108(0.25) C109(0.25) H109(0.25) C110(0.25) H110(0.25)
 C111(0.25) H111(0.25) C106(0.25) H106(0.25)
7.a Ternary CH refined with riding coordinates:
 C5(H5), C27(H27), C30(H30), C15(H15), C18(H18)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C22(H22), C12(H12), C24(H24), C11(H11), C23(H23), C52(H52),
 C56(H56), C53(H53), C55(H55), C54(H54), C1B(H1B), C1C(H1C), C1D(H1D), C1E(H1E),
  C1F(H1F), C101(H101), C102(H102), C103(H103), C104(H104), C105(H105),
 C100(H100), C107(H107), C108(H108), C109(H109), C110(H110), C111(H111),
 C106(H106)
7.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C3(H3A,H3B,H3C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C),
 C29(H29A,H29B,H29C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C14(H14A,H14B,
 H14C), C31(H31A,H31B,H31C), C16(H16A,H16B,H16C), C50(H50A,H50B,H50C), C2(H2A,
 H2B,H2C)
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_shelx_res_checksum              25274
_shelx_hkl_checksum              1633
_olex2_submission_special_instructions 'No special instructions were received'