Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1,1'-spirobiindane-based bisoxazoline (TMSI-BOX) ligands.
Gu, Haorui; Huang, Shaoying; Lin, Xufeng; Organic & biomolecular chemistry 17 (2019) 1154–1162; doi:10.1039/c8ob03065k

data_7156637
_publ_section_title
;
 Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using
 chiral tetramethyl-1,1'-spirobiindane-based bisoxazoline (TMSI-BOX)
 ligands.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1154
_journal_page_last               1162
_journal_paper_doi               10.1039/c8ob03065k
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C51 H46 N2 O2'
_chemical_formula_sum            'C51 H46 N2 O2'
_chemical_formula_weight         718.90
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-20 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   19.3333(8)
_cell_length_b                   13.2563(5)
_cell_length_c                   24.6689(10)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.79
_cell_volume                     5979.6(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.1029
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            102590
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.488
_diffrn_reflns_theta_min         1.893
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1894 before and 0.1199 after correction.
The Ratio of minimum to maximum transmission is 0.7269.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       needle
_exptl_crystal_F_000             2292
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 7589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.34(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1498
_refine_ls_number_reflns         21886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0802
_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^)+(0.1237P)^2^+3.9017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                19537
_reflns_number_total             21886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob03065k2.cif
_cod_data_source_block           181105_ghr_tm_l7_0m
_cod_depositor_comments          'Adding full bibliography for 7156637.cif.'
_cod_database_code               7156637
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.868
_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:
 C19(H19), C20(H20), C38(H38), C39(H39), C70(H70), C71(H71), C89(H89),
 C90(H90), C121(H121), C122(H122), C140(H140), C141(H141)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C59(H59A,H59B), C61(H61A,H61B), C110(H11A,H11B),
 C112(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
 C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C66(H66), C67(H67),
  C68(H68), C73(H73), C74(H74), C75(H75), C76(H76), C77(H77), C79(H79),
 C80(H80), C81(H81), C82(H82), C83(H83), C92(H92), C93(H93), C94(H94), C95(H95),
  C96(H96), C98(H98), C99(H99), C100(H100), C101(H101), C102(H102), C103(H103),
 C104(H104), C105(H105), C117(H117), C118(H118), C119(H119), C124(H124),
 C125(H125), C126(H126), C127(H127), C128(H128), C130(H130), C131(H131),
 C132(H132), C133(H133), C134(H134), C143(H143), C144(H144), C145(H145),
 C146(H146), C147(H147), C149(H149), C150(H150), C151(H151), C152(H152),
 C153(H153)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C), C87(H87A,
 H87B,H87C), C135(H13A,H13B,H13C), C136(H13D,H13E,H13F), C137(H13G,H13H,H13I),
 C138(H13J,H13K,H13L)
;
_shelx_res_checksum              27966
_olex2_submission_special_instructions 'No special instructions were received'