Iodine-Catalyzed Direct C‒H Alkenylation of Azaheterocycle N-Oxides with Alkenes
Zhang, Zhenhao; Pi, Chao; Tong, Heng; Cui, Xiuling; Wu, Yangjie; Organic Letters  (2017) –; doi:10.1021/acs.orglett.6b03399

data_1545142
_publ_section_title
;
 Iodine-Catalyzed Direct C--H Alkenylation of Azaheterocycle N-Oxides with
 Alkenes
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.6b03399
_journal_year                    2017
_chemical_formula_moiety         '2(C17 H13 N), C17 H10 N'
_chemical_formula_sum            'C51 H39 N3'
_chemical_formula_weight         693.85
_chemical_name_systematic
;
 ?
;
_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             2016-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.733(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5882(3)
_cell_length_b                   19.6254(8)
_cell_length_c                   14.7997(6)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6830
_cell_measurement_theta_min      4.0560
_cell_volume                     1907.02(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     64.00  90.00   1.00    9.00    --   18.07-178.00 150.00   26
  2  \w    -46.00  67.00   1.00    9.00    --   18.07   0.00 -30.00  113
  3  \w      7.00  81.00   1.00    9.00    --   18.07  57.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0533461000
_diffrn_orient_matrix_UB_12      -0.0092734000
_diffrn_orient_matrix_UB_13      0.0417674000
_diffrn_orient_matrix_UB_21      0.0389574000
_diffrn_orient_matrix_UB_22      -0.0292373000
_diffrn_orient_matrix_UB_23      -0.0208289000
_diffrn_orient_matrix_UB_31      0.0854677000
_diffrn_orient_matrix_UB_32      0.0191281000
_diffrn_orient_matrix_UB_33      -0.0115727000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.407
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0047(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0619
_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^)+(0.0615P)^2^+0.3659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2298
_reflns_number_total             3895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03399_si_002.cif
_cod_data_source_block           20160323
_cod_original_cell_volume        1907.03(15)
_cod_database_code               1545142
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20n4o4
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C27, N2}
3. Uiso/Uaniso restraints and constraints
Uiso(C27) = Uiso(N2)
4. Others
 Fixed Sof: N2(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
  C25(H25), C26(H26)
;
_shelx_res_checksum              49487
_shelx_hkl_checksum              38412
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.840