Cascade C-H Annulation of Aldoximes with Alkynes Using O2 as the Sole Oxidant: One-Pot Access to Multisubstituted Protoberberine Skeletons.
Tang, Junbin; Li, Shiqing; Liu, Zheng; Zhao, Yinsong; She, Zhijie; Kadam, Vilas D.; Gao, Ge; Lan, Jingbo; You, Jingsong; Organic letters 19 (2017) 604–607; doi:10.1021/acs.orglett.6b03772

data_1545087
_publ_section_title
;
 Cascade C-H Annulation of Aldoximes with Alkynes Using O2 as the Sole
 Oxidant: One-Pot Access to Multisubstituted Protoberberine Skeletons.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              604
_journal_page_last               607
_journal_paper_doi               10.1021/acs.orglett.6b03772
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C36 H31 N O'
_chemical_formula_sum            'C36 H31 N O'
_chemical_formula_weight         493.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.777(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0097(3)
_cell_length_b                   13.4734(3)
_cell_length_c                   18.1820(4)
_cell_measurement_reflns_used    7451
_cell_measurement_temperature    294.98(11)
_cell_measurement_theta_max      72.1560
_cell_measurement_theta_min      4.0470
_cell_volume                     2672.28(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  -30.0000 74

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -180.0000 74

  3 omega  -33.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171    0.0000 -150.0000 139

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000    0.0000 84

  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -150.0000 84

  6 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   38.0000  -90.0000 88

  7 omega   40.00   98.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

  8 omega   38.00   91.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

  9 omega   40.00   98.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 10 omega   39.00  109.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 11 omega   40.00   98.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 12 omega   38.00   91.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 13 omega   38.00   91.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 14 omega   39.00  109.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 15 omega   38.00   91.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 16 omega   38.00   91.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 17 omega   91.00  176.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 18 omega   87.00  178.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 19 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000   30.0000 94

 20 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   90.0000 84

 21 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000    0.0000 84

 22 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000  -60.0000 84

 23 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000 -150.0000 84

 24 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000 -150.0000 94

 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  120.0000 94

 26 omega   87.00  134.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   31.0000  136.0065 47

 27 omega   39.00  109.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 28 omega   70.00  178.00   1.0000    3.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0300430000
_diffrn_orient_matrix_UB_12      0.0499405000
_diffrn_orient_matrix_UB_13      -0.0765617000
_diffrn_orient_matrix_UB_21      0.1099209000
_diffrn_orient_matrix_UB_22      -0.0530987000
_diffrn_orient_matrix_UB_23      -0.0267270000
_diffrn_orient_matrix_UB_31      -0.0833185000
_diffrn_orient_matrix_UB_32      -0.0880734000
_diffrn_orient_matrix_UB_33      -0.0273137000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.719
_diffrn_reflns_theta_min         4.097
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0950P)^2^+0.2650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4281
_reflns_number_total             5264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03772_si_002.cif
_cod_data_source_block           tjb-01
_cod_depositor_comments          'Adding full bibliography for 1545087.cif.'
_cod_original_cell_volume        2672.29(10)
_cod_database_code               1545087
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C007(H007), C008(H008), C00A(H00A), C00C(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-01
_olex2_submission_special_instructions 'No special instructions were received'