Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics
Wei, Jinhu; Cao, Bei; Tse, Chun-Wai; Chang, Xiao-Yong; Zhou, Cong-Ying; Che, Chi-Ming; Chemical Science 11 (2020) 684–693; doi:10.1039/C9SC04858H

data_1556082
_publ_section_title
;
 Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality
 for highly regio- and enantioselective alkylation of N-heteroaromatics
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              684
_journal_page_last               693
_journal_paper_doi               10.1039/C9SC04858H
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H26 N3 O'
_chemical_formula_sum            'C24 H26 N3 O'
_chemical_formula_weight         372.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-11-01 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5973(8)
_cell_length_b                   5.0981(2)
_cell_length_c                   17.5377(7)
_cell_measurement_reflns_used    3976
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.78
_cell_measurement_theta_min      8.94
_cell_volume                     1930.07(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12271
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.965
_diffrn_reflns_theta_min         2.521
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.8429.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       needle
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0383P)^2^+1.2022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3351
_reflns_number_total             3358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04858h2.cif
_cod_data_source_block           cxy290m
_cod_depositor_comments
;Adding full bibliography for 1556080--1556083.cif.

 Adding full bibliography for 1556080--1556083.cif.
;
_cod_database_code               1556082
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              6089
_olex2_submission_special_instructions 'No special instructions were received'