A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes.
Markey, Sophie J.; Lewis, William; Moody, Christopher J.; Organic letters 15 (2013) 6306–6308; doi:10.1021/ol403191k

data_1513249
_publ_section_title
;
 A New Route to \a-Carbolines Based on 6\p-Electrocyclization of
 Indole-3-alkenyl Oximes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6306
_journal_page_last               6308
_journal_paper_doi               10.1021/ol403191k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-02
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 119.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.051(3)
_cell_length_b                   4.7507(6)
_cell_length_c                   15.792(3)
_cell_measurement_reflns_used    1766
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.85
_cell_measurement_theta_min      5.48
_cell_volume                     1052.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
  1 omega  -65.00   23.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000   60.0000 44

  2 omega  -68.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000 -180.0000 46

  3 omega   25.00   63.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   57.0000  -60.0000 19

  4 omega   62.00   88.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000  -60.0000 13

  5 omega   39.00   69.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   30.0000 15

  6 omega   48.00   78.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   60.0000 15

  7 omega   33.00   69.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 18

  8 omega   33.00   59.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000    0.0000 13

  9 omega   86.00  148.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000 -120.0000 31

 10 omega   36.00   64.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -60.0000 14

 11 omega   38.00   70.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   28.0000 16

 12 omega   33.00   69.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  120.0000 18

 13 omega   43.00   69.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -30.0000 13

 14 omega   46.00  110.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000 -180.0000 32

 15 omega   87.00  157.00   2.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  -90.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0893304000
_diffrn_orient_matrix_UB_12      -0.0455378000
_diffrn_orient_matrix_UB_13      -0.0992829000
_diffrn_orient_matrix_UB_21      -0.0450565000
_diffrn_orient_matrix_UB_22      -0.1778791000
_diffrn_orient_matrix_UB_23      0.0487348000
_diffrn_orient_matrix_UB_31      -0.0453594000
_diffrn_orient_matrix_UB_32      0.2672728000
_diffrn_orient_matrix_UB_33      0.0155090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4141
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.020
_diffrn_reflns_theta_min         5.603
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.317
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.6693
_exptl_crystal_size_mid          0.1385
_exptl_crystal_size_min          0.0692
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0548P)^2^+0.4778P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1823
_reflns_number_total             2059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403191k_si_001.cif
_cod_data_source_block           sjmcmb
_cod_database_code               1513249
_nottingham_internal_coll_name   SJMCMB
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '3.0000 and 5.0000'
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   22/6/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 22/06/2012
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_chemical_oxdiff_formula         'C13 H10 N2 O'
_chemical_oxdiff_usercomment
'SJMCMB #11596 IN FOMBLIN FIML ON MICROMOUNT FOR SJM/CJM'
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), N9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelxl_version_number           2013-2