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_1513250
_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 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 101.762(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9779(7)
_cell_length_b                   5.7825(3)
_cell_length_c                   18.2629(15)
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.36
_cell_measurement_theta_min      4.49
_cell_volume                     1031.59(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
(compiled Dec 19 2012,11:08:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
(compiled Dec 19 2012,11:08:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
(compiled Dec 19 2012,11:08:27)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9755
_diffrn_measurement_details
;
  1 omega  -98.00  -26.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7877  -57.0000  150.0000 36

  2 omega  -69.00    5.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.7877   57.0000   90.0000 37

  3 omega    7.00   55.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877  -38.0000 -180.0000 24

  4 omega   42.00   68.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   60.0000 13

  5 omega   33.00   91.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -95.0000   60.0000 29

  6 omega   33.00   67.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000 -180.0000 17

  7 omega   39.00   77.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000   30.0000 19

  8 omega   34.00   62.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  -90.0000 14

  9 omega   41.00  121.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000 -150.0000 40

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

 11 omega   85.00  153.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  150.0000 34

 12 omega   49.00   75.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000 -150.0000 13

 13 omega   56.00  142.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -163.0000   82.0000 43

 14 omega   19.00  111.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000   90.0000 46

 15 omega   19.00  111.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000  -90.0000 46

 16 omega   19.00  111.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.7877   57.0000    0.0000 46

 17 omega   66.00  158.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   15.0000   90.0000 46

 18 omega   83.00  157.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000 -150.0000 37

 19 omega   80.00  158.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   61.0000  -90.0000 39

 20 omega   36.00   76.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 20

 21 omega   36.00   76.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  150.0000 20

 22 omega   83.00  151.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   45.0000  -30.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1340900000
_diffrn_orient_matrix_UB_12      0.0278560000
_diffrn_orient_matrix_UB_13      -0.0285586000
_diffrn_orient_matrix_UB_21      -0.0017739000
_diffrn_orient_matrix_UB_22      0.2620379000
_diffrn_orient_matrix_UB_23      0.0149818000
_diffrn_orient_matrix_UB_31      0.0828827000
_diffrn_orient_matrix_UB_32      -0.0390197000
_diffrn_orient_matrix_UB_33      0.0799468000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8267
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.657
_diffrn_reflns_theta_min         4.947
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.408
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
(compiled Dec 19 2012,11:08:27)
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    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4123
_exptl_crystal_size_mid          0.3029
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.4826P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1922
_reflns_number_total             2057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403191k_si_001.cif
_cod_data_source_block           sjmcmc
_cod_original_cell_volume        1031.60(13)
_cod_database_code               1513250
_nottingham_internal_coll_name   SJMCMC
_nottingham_internal_coll_number 12201
_nottingham_internal_coll_client SJM/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time 2.0000
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   4/2/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 04/02/2013
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_chemical_oxdiff_formula         'C13 H12 N2 O'
_chemical_oxdiff_usercomment
'SJMCMC #12201 IN FOMBLIN FILM ON MICROMOUNT FOR SJM/CJM'
_reflns_odcompleteness_completeness 99.71
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), N9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelxl_version_number           2013-2