Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones.
Stewart, Scott G.; Ghisalberti, Emilio L.; Skelton, Brian W.; Heath, Charles H.; Organic & biomolecular chemistry 8 (2010) 3563–3570; doi:10.1039/c003742g

data_7153366
_publ_section_title
;
 Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone
 reaction in the formation of novel benzo[c]naphthyridinones.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3563
_journal_page_last               3570
_journal_paper_doi               10.1039/c003742g
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H15 F3 N2 O4'
_chemical_formula_sum            'C15 H15 F3 N2 O4'
_chemical_formula_weight         344.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_atom_sites_solution_hydrogens   geom
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_audit_creation_date             2009-09-17T20:53:38-00:00
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   10.0807(2)
_cell_length_b                   19.0872(4)
_cell_length_c                   22.9900(5)
_cell_measurement_reflns_used    21572
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.5828
_cell_measurement_theta_min      3.6548
_cell_volume                     4423.56(16)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Oxford Diffraction Gemini, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0056560125
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_diffrn_orient_matrix_UB_13      -0.0246585819
_diffrn_orient_matrix_UB_21      -0.0285675179
_diffrn_orient_matrix_UB_22      -0.0264659535
_diffrn_orient_matrix_UB_23      0.0177020127
_diffrn_orient_matrix_UB_31      -0.0640510718
_diffrn_orient_matrix_UB_32      0.0137338226
_diffrn_orient_matrix_UB_33      -0.0057109293
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0447
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_diffrn_reflns_number            59406
_diffrn_reflns_theta_full        31.5
_diffrn_reflns_theta_max         32.64
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_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.97567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         8485
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                6891
_reflns_number_total             8485
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c003742g.txt
_cod_data_source_block           ch4651
_cod_database_code               7153366