Efficient construction of cyclopenta[b]quinoline core of isoschizozygane alkaloids via intramolecular formal hetero-Diels-Alder reaction.
Magomedov, Nabi A.; Organic letters 5 (2003) 2509–2512; doi:10.1021/ol034776r

data_1507334
_publ_section_title
;
 Efficient construction of cyclopenta[b]quinoline core of isoschizozygane
 alkaloids via intramolecular formal hetero-Diels-Alder reaction.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2509
_journal_page_last               2512
_journal_paper_doi               10.1021/ol034776r
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C17 H24 Cl N O'
_chemical_formula_weight         293.82
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.2950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8243(10)
_cell_length_b                   12.3639(8)
_cell_length_c                   17.7016(12)
_cell_measurement_temperature    293(2)
_cell_volume                     3181.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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  0.0160
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_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9763
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   'empirical SADABS'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.052
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+3.0140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                3087
_reflns_number_total             3737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034776rsi20030507_013256.cif
_cod_data_source_block           sad
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'na' 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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1507334