Oxidative Rearrangement of Indoles: A New Approach to the EFHG-Tetracyclic Core of Diazonamide A
Cyril Poriel; Mathilde Lachia; Claire Wilson; James R. Davies; Christopher J. Moody; Journal of Organic Chemistry 72 (2007) 2978–2987; doi:10.1021/jo062627r

data_4022845
_publ_contact_author             'Prof. C.J. Moody'
_publ_contact_author_address
;
School of Chemistry
University of Nottingham
University Park
Nottingham
NG7 2RD
;
_publ_contact_author_email       c.j.moody@nottingham.ac.uk
_publ_section_title
;
 Oxidative Rearrangement of Indoles: A New Approach to
 the EFHG-Tetracyclic Core of Diazonamide A
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2978
_journal_page_last               2987
_journal_paper_doi               10.1021/jo062627r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C17 H15 Br N2 O3'
_chemical_formula_weight         375.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.396(1)
_cell_angle_beta                 77.900(1)
_cell_angle_gamma                71.556(1)
_cell_formula_units_Z            2
_cell_length_a                   7.9118(7)
_cell_length_b                   9.4898(8)
_cell_length_c                   11.6979(10)
_cell_measurement_reflns_used    2892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.75
_cell_volume                     814.66(12)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6878
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS v2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.4647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                3179
_reflns_number_total             3625
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo062627rsi20070130_025609_1.cif
_cod_data_source_block           4c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022845