A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate
Zhou, Shuai; Xu, Xiaojuan; Zhu, Xu; Zheng, Yu; Chen, Sufang; Xue, Mingqiang; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00640E

data_7158700
_publ_section_title
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 A facile approach to C-functionalized \b-ketoimine compounds via terminal
 alkylation of a tetralithiated intermediate
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00640E
_journal_year                    2022
_chemical_formula_moiety         'C64 H96 Li8 N4 O12'
_chemical_formula_sum            'C64 H96 Li8 N4 O12'
_chemical_formula_weight         1168.96
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-27 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                88.701(2)
_cell_angle_beta                 78.029(2)
_cell_angle_gamma                82.275(2)
_cell_formula_units_Z            1
_cell_length_a                   9.4644(5)
_cell_length_b                   12.0676(7)
_cell_length_c                   15.1154(8)
_cell_measurement_reflns_used    5201
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      2.20
_cell_volume                     1673.47(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.02
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0741
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.612
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7665
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.8710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4655
_reflns_number_total             7665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00640e2.cif
_cod_data_source_block           mo_b191010b_0m_a
_cod_database_code               7158700
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Li4-Li3
 3 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C30(H30A,H30B), C25(H25A,H25B), C15(H15A,H15B), C31(H31A,
 H31B), C29(H29A,H29B), C28(H28A,H28B), C32(H32A,H32B), C26(H26A,H26B),
 C12(H12A,H12B), C27(H27A,H27B), C14(H14A,H14B), C19(H19A,H19B), C17(H17A,H17B),
  C18(H18A,H18B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C9(H9), C22(H22), C6(H6), C1(H1)
3.c X=CH2 refined with riding coordinates:
 C24(H24A,H24B), C11(H11A,H11B)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              80914
_olex2_submission_special_instructions 'No special instructions were received'