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_7110610
_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            'C22 H25 N O6'
_chemical_formula_weight         399.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.726(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6487(14)
_cell_length_b                   22.172(3)
_cell_length_c                   8.588(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.6
_cell_measurement_theta_min      9.35
_cell_volume                     2017.5(6)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'NRCSDP DATARD2'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
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_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   psi
_exptl_crystal_colour            colorles
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_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.025
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_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0049(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_goodness_of_fit_obs   1.225
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
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_refine_ls_restrained_S_obs      1.225
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_obs          0.0430
_refine_ls_shift/esd_max         0.013
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.0989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1403
_refine_ls_wR_factor_obs         0.1261
_reflns_number_observed          2267
_reflns_number_total             3545
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904366gsup1.cif
_cod_data_source_block           ic6143
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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^)+(0.0767P)^2^+0.0989P] 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^)+(0.0767P)^2^+0.0989P] 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        2017.5(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7110610