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_7132027
_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         'C54 H49 B F15 N2 O5 P Sn, C7 H8, 1.2(C6 H6)'
_chemical_formula_sum            'C68.2 H64.2 B F15 N2 O5 P Sn'
_chemical_formula_weight         1437.28
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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   geom
_audit_creation_date             2023-02-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                100.891(4)
_cell_angle_beta                 108.982(4)
_cell_angle_gamma                111.357(3)
_cell_formula_units_Z            2
_cell_length_a                   14.6414(9)
_cell_length_b                   15.4756(10)
_cell_length_c                   17.6749(14)
_cell_measurement_reflns_used    9409
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      2.82
_cell_volume                     3305.2(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0929
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            113680
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.821
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.117
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5533
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1340 before and 0.0908 after correction.
The Ratio of minimum to maximum transmission is 0.7347.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             1465
_refine_diff_density_max         0.745
_refine_diff_density_min         -1.326
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     896
_refine_ls_number_reflns         11672
_refine_ls_number_restraints     232
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0980P)^2^+1.9882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10345
_reflns_number_total             11672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03117a2.cif
_cod_data_source_block           12345_CCDC1
_cod_original_formula_sum        'C68.20 H64.20 B F15 N2 O5 P Sn'
_cod_database_code               7132027
_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
 C10-C7 = C8-C9 = C9-C11
 1.37 with sigma of 0.02
 C10-C11
 1.38 with sigma of 0.02
 C7-C12 = C12-C8
 1.36 with sigma of 0.02
 C3-C4 = C6-C1 = C1-C2
 1.37 with sigma of 0.02
 C3-C2
 1.38 with sigma of 0.02
 C4-C5 = C5-C6
 1.36 with sigma of 0.02
 C10-C9
 2.38 with sigma of 0.04
 C10-C12 = C12-C9 = C8-C11
 2.37 with sigma of 0.04
 C7-C8
 2.36 with sigma of 0.04
 C3-C5 = C5-C1 = C6-C2
 2.37 with sigma of 0.04
 C3-C1
 2.38 with sigma of 0.04
 C4-C6
 2.36 with sigma of 0.04
 C10-C7 \\sim C7-C12 \\sim C12-C8 \\sim C8-C9 \\sim C9-C11 \\sim C11-C10
 with sigma of 0.02
 C10-C9 \\sim C10-C12 \\sim C9-C12 \\sim C8-C7 \\sim C8-C11 \\sim C11-C7
 with sigma of 0.04
 C3-C4 \\sim C4-C5 \\sim C5-C6 \\sim C6-C1 \\sim C1-C2 \\sim C2-C3
 with sigma of 0.02
 C3-C1 \\sim C3-C5 \\sim C1-C5 \\sim C6-C4 \\sim C6-C2 \\sim C2-C4
 with sigma of 0.04
3. Restrained planarity
 C10, C7, C12, C8, C9, C11
 with sigma of 0.1
 C3, C4, C5, C6, C1, C2
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C10, C7, C12, C8, C9, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, C4, C5, C6, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C10(0.7) H10(0.7) C7(0.7) H7(0.7) C12(0.7) H12(0.7) C8(0.7)
 H8(0.7) C9(0.7) H9(0.7) C11(0.7) H11(0.7) C3(0.5) H3(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6(0.5) C1(0.5) H1(0.5) C2(0.5) H2(0.5)
7.a Ternary CH refined with riding coordinates:
 C016(H016), C017(H017), C018(H018), C01G(H01G), C01J(H01J), C029(H029)
7.b Aromatic/amide H refined with riding coordinates:
 C00Q(H00Q), C00V(H00V), C00Y(H00Y), C019(H019), C01M(H01M), C01P(H01P),
 C01T(H01T), C01X(H01X), C01Y(H01Y), C026(H026), C027(H027), C028(H028),
 C10(H10), C7(H7), C12(H12), C8(H8), C9(H9), C11(H11), C3(H3), C4(H4), C5(H5),
 C6(H6), C1(H1), C2(H2)
7.c Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01D(H01D,H01E,H01F), C01K(H01H,H01I,H01K), C01O(H01L,
 H01N,H01O), C01W(H01Q,H01R,H01S), C020(H02A,H02B,H02C), C022(H02D,H02E,H02F),
 C025(H02G,H02H,H02I), C02A(H02V,H02W,H02X), C02B(H02J,H02K,H02L), C02C(H02M,
 H02N,H02O), C02D(H02P,H02Q,H02R), C02E(H02S,H02T,H02U)
;
_shelx_res_checksum              64321
_shelx_hkl_checksum              71364
_olex2_submission_special_instructions 'No special instructions were received'