Selective Construction of Quaternary Stereocentres in Radical Cyclisation Cascades triggered by electron-transfer reduction of amide-type carbonyls
Huang, Huan-Ming; Bonilla, Pablo; Procter, David John; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00739F

data_7155574
_publ_section_title
;
 Selective Construction of Quaternary Stereocentres in Radical Cyclisation
 Cascades triggered by electron-transfer reduction of amide-type carbonyls
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00739F
_journal_year                    2017
_chemical_formula_moiety         'C33 H40 N2 O4'
_chemical_formula_sum            'C33 H40 N2 O4'
_chemical_formula_weight         528.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-30
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
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2017-01-24 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                76.664(5)
_cell_angle_beta                 63.649(6)
_cell_angle_gamma                70.861(5)
_cell_formula_units_Z            2
_cell_length_a                   11.4817(6)
_cell_length_b                   11.8623(7)
_cell_length_c                   12.3995(7)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.1700
_cell_measurement_theta_min      4.0600
_cell_volume                     1422.43(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_details
;
  1 omega  -17.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5361   57.0000  -30.0000 95

  2 omega  -15.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5361   37.0000 -150.0000 97

  3 omega  -58.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5361  -37.0000   30.0000 91

  4 omega  -76.00  -40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.5361  178.0000   30.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0689019000
_diffrn_orient_matrix_UB_12      -0.0134560000
_diffrn_orient_matrix_UB_13      -0.0400852000
_diffrn_orient_matrix_UB_21      0.0065182000
_diffrn_orient_matrix_UB_22      -0.0615419000
_diffrn_orient_matrix_UB_23      0.0219188000
_diffrn_orient_matrix_UB_31      -0.0174179000
_diffrn_orient_matrix_UB_32      -0.0088572000
_diffrn_orient_matrix_UB_33      -0.0450511000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.687
_diffrn_reflns_theta_min         3.426
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0741
_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^)+(0.0935P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.2091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3806
_reflns_number_total             6621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00739f2.cif
_cod_data_source_block           odjp001
_cod_original_cell_volume        1422.42(16)
_cod_database_code               7155574
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.81
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C33A(0.5) H33A(0.5) H33B(0.5) H33C(0.5) C33B(0.5) H33D(0.5)
 H33E(0.5) H33F(0.5)
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,
 H24B), C26(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C28(H28), C29(H29), C31(H31), C32(H32)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C25(H25A,H25B,H25C), C33A(H33A,H33B,H33C), C33B(H33D,H33E,H33F)
;
_shelx_res_checksum              30385
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'