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_1513248
_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         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.893(15)
_cell_length_b                   8.972(9)
_cell_length_c                   7.742(8)
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.27
_cell_volume                     1034.5(18)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_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      90(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7776
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.661
_diffrn_reflns_theta_min         2.270
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/2 (Bruker,2007) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0904 after correction.
The Ratio of minimum to maximum transmission is 0.6370.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0658
_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^)+(0.1268P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1898
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                1761
_reflns_number_total             2339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403191k_si_001.cif
_cod_data_source_block           sjmcma
_cod_original_cell_volume        1034.6(18)
_cod_database_code               1513248
_nottingham_internal_coll_name   SJMCMA
_nottingham_internal_coll_number 11575
_nottingham_internal_coll_client SJM/CJM
_nottingham_internal_coll_type   sphere
_nottingham_internal_coll_frame_time 30
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_frame_method \w
_nottingham_internal_coll_user   wl
_nottingham_internal_coll_date   21/6/2012
_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
_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:
 N1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelxl_version_number           2013-2