Radical-mediated intramolecular β-C(sp<sup>3</sup>)-H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols.
Mou, Xue-Qing; Chen, Xiang-Yu; Chen, Gong; He, Gang; Chemical communications (Cambridge, England) 54 (2018) 515–518; doi:10.1039/c7cc08897c

data_7120999
_publ_section_title
;
 Radical-mediated intramolecular \b-C(sp<sup>3</sup>)-H amidation of
 alkylimidates: facile synthesis of 1,2-amino alcohols.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              515
_journal_page_last               518
_journal_paper_doi               10.1039/c7cc08897c
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration s
_chemical_formula_moiety         'C41 H55 N O3'
_chemical_formula_sum            'C41 H55 N O3'
_chemical_formula_weight         609.86
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc1pf65h
_audit_creation_date             2017-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-07-12 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.085(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4864(8)
_cell_length_b                   11.3225(6)
_cell_length_c                   22.7080(11)
_cell_measurement_reflns_used    6261
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      24.9110
_cell_measurement_theta_min      3.2910
_cell_volume                     3578.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.2116
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -22.00   92.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   19.0000    0.0000 114

  2 omega   62.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   77.0000 -180.0000 26

  3 omega   22.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -99.0000  -60.0000 39

  4 omega  -10.00   25.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396   77.0000 -180.0000 35

  5 omega  -20.00   60.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -99.0000   60.0000 80

  6 omega  -47.00   34.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9396  -57.0000 -180.0000 81

  7 omega  -71.00  -46.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2521  178.0000    0.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0259580000
_diffrn_orient_matrix_UB_12      0.0238358000
_diffrn_orient_matrix_UB_13      0.0287159000
_diffrn_orient_matrix_UB_21      -0.0149490000
_diffrn_orient_matrix_UB_22      0.0576215000
_diffrn_orient_matrix_UB_23      -0.0107788000
_diffrn_orient_matrix_UB_31      -0.0412027000
_diffrn_orient_matrix_UB_32      -0.0058499000
_diffrn_orient_matrix_UB_33      0.0108384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24100
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_min         2.927
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         11746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0641
_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^)+(0.0460P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                7938
_reflns_number_total             11746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08897c2.cif
_cod_data_source_block           p170311f-p
_cod_depositor_comments
'Adding full bibliography for 7120999--7121000.cif.'
_cod_database_code               7120999
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     MXQ-2-114
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C24(H24), C15(H15), C16(H16), C70(H70), C25(H25), C65(H65), C66(H66),
 C29(H29), C73(H73), C57(H57), C35(H35), C32(H32), C76(H76), C56(H56), C39(H39),
  C80(H80)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C72(H72A,H72B), C26(H26A,H26B), C27(H27A,
 H27B), C61(H61A,H61B), C23(H23A,H23B), C67(H67A,H67B), C71(H71A,H71B),
 C60(H60A,H60B), C37(H37A,H37B), C68(H68A,H68B), C30(H30A,H30B), C31(H31A,H31B),
  C36(H36A,H36B), C64(H64A,H64B), C77(H77A,H77B), C78(H78A,H78B), C38(H38A,
 H38B), C79(H79A,H79B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), N1(H1), C22(H22), C46(H46), C63(H63), C42(H42), C45(H45), C12(H12),
 C1(H1A), C5(H5), C8(H8), C43(H43), C44(H44), C9(H9), C10(H10), C4(H4), C3(H3),
 C11(H11), C2(H2), C53(H53), C49(H49), C52(H52), C50(H50), C51(H51)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C33(H33A,H33B,H33C), C74(H74A,H74B,H74C), C62(H62A,H62B,
 H62C), C34(H34A,H34B,H34C), C75(H75A,H75B,H75C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C81(H81A,H81B,H81C), C82(H82A,H82B,H82C)
;
_olex2_submission_special_instructions 'No special instructions were received'