Diels–Alder and Michael addition reactions of indoles with masked o-benzoquinones: synthesis of highly functionalized hydrocarbazoles and 3-arylindoles
Hsieh, Ming-Fang; Rao, Polisetti Dharma; Liao, Chun-Chen; Chemical Communications  (1999) 1441–; doi:10.1039/a904366g

data_7110611
_publ_section_title
;
 Diels--Alder and Michael addition reactions of indoles with masked
 o-benzoquinones: synthesis of highly functionalized hydrocarbazoles and
 3-arylindoles
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              1441
_journal_paper_doi               10.1039/a904366g
_journal_year                    1999
_chemical_formula_sum            'C17 H14 Br N O4'
_chemical_formula_weight         376.20
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.7060(10)
_cell_angle_beta                 96.9180(10)
_cell_angle_gamma                117.1930(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0176(2)
_cell_length_b                   9.4144(2)
_cell_length_c                   10.36370(10)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     774.62(3)
_computing_cell_refinement       'Smart (Siemens, 1995)'
_computing_data_collection       'Smart (Siemens, 1995)'
_computing_data_reduction        'Smart (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL-PLUS (Siemens, 1994)'
_computing_publication_material  'SHELXTL-PLUS (Siemens, 1994)'
_computing_structure_refinement  'SHELXTL-PLUS (Siemens, 1994)'
_computing_structure_solution    'SHELXTL-PLUS (Siemens, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens Smart CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7349
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    2.673
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     SHELXL
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_refine_ls_goodness_of_fit_obs   1.178
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     0
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_refine_ls_restrained_S_obs      1.178
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_obs          0.0349
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.4249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0957
_refine_ls_wR_factor_obs         0.0893
_reflns_number_observed          2952
_reflns_number_total             3317
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904366gsup1.cif
_cod_data_source_block           ot17m
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.4249P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.4249P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        774.62(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7110611