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_4022757
_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         'C28 H20 Br Cl N2 O2'
_chemical_formula_sum            'C28 H20 Br Cl N2 O2'
_chemical_formula_weight         531.82
_chemical_melting_point          200(1)
_chemical_name_systematic
; 
 12-bromo-14-chloro-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 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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.523(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.701(7)
_cell_length_b                   13.626(5)
_cell_length_c                   7.846(3)
_cell_measurement_reflns_used    3033
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.20
_cell_measurement_theta_min      2.42
_cell_volume                     2294.2(13)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0755
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16410
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_correction_T_min  0.4564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          1.456
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2499
_reflns_number_total             4494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062321krom20061110_081836.cif
_cod_data_source_block           rn11
_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/c'
_cod_database_code               4022757