A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(ii) catalysis.
Ruvinskaya, Julia O.; Rostovskii, Nikolai V.; Filippov, Ilya P.; Khlebnikov, Alexander F.; Novikov, Mikhail S.; Organic & biomolecular chemistry 16 (2017) 38–42; doi:10.1039/c7ob02637d

data_7156013
_publ_section_title
;
 A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of
 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under
 Rh(ii) catalysis.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              38
_journal_page_last               42
_journal_paper_doi               10.1039/c7ob02637d
_journal_volume                  16
_journal_year                    2017
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-13
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2017-10-13 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5664(3)
_cell_length_b                   8.8236(5)
_cell_length_c                   28.6221(19)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2370
_cell_measurement_theta_min      3.6780
_cell_volume                     1405.79(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -2.00   96.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  150.0000 98

  2 omega   -7.00   59.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 66

  3 omega  -49.00  -23.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000 -150.0000 26

  4 omega   17.00   45.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000  -60.0000 28
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_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_12      0.0349351000
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_diffrn_orient_matrix_UB_21      0.0190845000
_diffrn_orient_matrix_UB_22      0.0720688000
_diffrn_orient_matrix_UB_23      -0.0103322000
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_diffrn_orient_matrix_UB_32      0.0066889000
_diffrn_orient_matrix_UB_33      -0.0042744000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6244
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       prizm
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0505
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_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^)+(0.0425P)^2^+0.1573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0924
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_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2693
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_cod_data_source_file            c7ob02637d2.cif
_cod_data_source_block           rnv27
_cod_depositor_comments          'Adding full bibliography for 7156013.cif.'
_cod_original_cell_volume        1405.79(15)
_cod_database_code               7156013
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C18 h15 N3 o1'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C17(H17), C16(H16), C2(H2), C8(H8), C7(H7), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              83130
_olex2_submission_special_instructions 'No special instructions were received'