A New Entry to Polycyclic Indole Derivatives via Intramolecular Imino Diels-Alder Reaction: Observation of Unexpected Reaction
Vikram Gaddam; Rajagopal Nagarajan; Journal of Organic Chemistry 72 (2007) 3573–3576; doi:10.1021/jo062321k

data_4022756
_publ_contact_author_address
; 
School of Chemistry
University of Hyderabad
Hyderabad
500046
India
;
_publ_contact_author_email       rnsc@uohyd.ernet.in
_publ_contact_author_fax         +91-40-23012460
_publ_contact_author_name        Dr.R.Nagarajan
_publ_contact_author_phone       +91-40-23134831
_publ_section_title
;
 A New Entry to Polycyclic Indole Derivatives via Intramolecular
 Imino Diels-Alder Reaction: Observation of Unexpected Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3573
_journal_page_last               3576
_journal_paper_doi               10.1021/jo062321k
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C56 H40 Cl4 N4 O4'
_chemical_formula_sum            'C56 H40 Cl4 N4 O4'
_chemical_formula_weight         974.72
_chemical_melting_point          208(1)
_chemical_name_systematic
; 
 12,14-dichloro-7,7-dimethyl-6,7,7a,8,14b,17-hexahydro-5H-benzo[5,6]
 pyrrolizino[2,1-c]naphtho[2,3-h]quinoline-5,17-dione 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.416(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9652(14)
_cell_length_b                   23.078(3)
_cell_length_c                   17.208(2)
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.59
_cell_measurement_theta_min      2.33
_cell_volume                     4640.8(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1435
_diffrn_reflns_av_sigmaI/netI    0.1676
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33905
_diffrn_reflns_theta_full        26.10
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         9115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.2182
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                3305
_reflns_number_total             9115
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062321krom20061110_080448.cif
_cod_data_source_block           rn10_m
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022756