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_1556083
_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         'C18 H21 N3 O'
_chemical_formula_sum            'C18 H21 N3 O'
_chemical_formula_weight         295.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-21
_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                 105.42(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.630(5)
_cell_length_b                   15.205(7)
_cell_length_c                   12.200(9)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.59
_cell_measurement_theta_min      2.91
_cell_volume                     1543.2(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24001
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.741
_diffrn_reflns_theta_min         3.758
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0833 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.8564.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_preparation       'vapor diffusion'
_exptl_crystal_recrystallization_method DCM/Hexane/Ether
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.21(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0541P)^2^+0.3422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                5468
_reflns_number_total             5484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04858h2.cif
_cod_data_source_block           cxy199_0m
_cod_depositor_comments
;Adding full bibliography for 1556080--1556083.cif.

 Adding full bibliography for 1556080--1556083.cif.
;
_cod_original_cell_volume        1543.4(17)
_cod_database_code               1556083
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20),
 C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C),
 C21(H21A,H21B,H21C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C)
;
_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'