Diastereodivergent [3 + 2] Annulation of Aromatic Aldimines with Alkenes via C-H Activation by Half-Sandwich Rare-Earth Catalysts.
Cong, Xuefeng; Zhan, Gu; Mo, Zhenbo; Nishiura, Masayoshi; Hou, Zhaomin; Journal of the American Chemical Society 142 (2020) 5531–5537; doi:10.1021/jacs.0c01171

data_4134391
_publ_section_title
;
 Diastereodivergent [3 + 2] Annulation of Aromatic Aldimines with Alkenes
 via C-H Activation by Half-Sandwich Rare-Earth Catalysts.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5531
_journal_page_last               5537
_journal_paper_doi               10.1021/jacs.0c01171
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C19 H22 I N'
_chemical_formula_sum            'C19 H22 I N'
_chemical_formula_weight         391.27
_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             2018-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                92.455(4)
_cell_angle_beta                 108.753(4)
_cell_angle_gamma                115.373(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8516(12)
_cell_length_b                   9.0513(12)
_cell_length_c                   13.0251(18)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.63
_cell_volume                     872.7(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0594
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13149
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.548
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.829
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0439P)^2^+0.7521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2846
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c01171_si_002.cif
_cod_data_source_block           cong01_0m_a
_cod_depositor_comments
'Adding full bibliography for 4134390--4134391.cif.'
_cod_database_code               4134391
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00K(H00Q), C00L(H00R)
2.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M), C00J(H00N,H00O,H00P)
;
_shelx_res_checksum              81159
_shelx_hkl_checksum              23064
_olex2_submission_special_instructions 'No special instructions were received'