Asymmetric organocatalytic synthesis of complex cyclopenta[b]quinoline derivatives.
Jensen, Kim L.; Dickmeiss, Gustav; Donslund, Bjarke S.; Poulsen, Pernille H.; Jørgensen, Karl Anker; Organic letters 13 (2011) 3678–3681; doi:10.1021/ol201328s

data_1502284
_publ_section_title
;
 Asymmetric organocatalytic synthesis of complex cyclopenta[b]quinoline
 derivatives.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3678
_journal_page_last               3681
_journal_paper_doi               10.1021/ol201328s
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 Br N2 O2, C H Cl3'
_chemical_formula_sum            'C27 H26 Br Cl3 N2 O2'
_chemical_formula_weight         596.76
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-03-07
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                111.413(2)
_cell_angle_beta                 100.8600(19)
_cell_angle_gamma                101.302(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9605(2)
_cell_length_b                   11.4468(3)
_cell_length_c                   13.0628(3)
_cell_measurement_reflns_used    23835
_cell_measurement_temperature    100.3
_cell_measurement_theta_max      28.8617
_cell_measurement_theta_min      2.1708
_cell_volume                     1303.38(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      100.3
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
  1 omega  -22.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.3082   77.0000  120.0000 92

  2 omega  -15.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.3082   38.0000   30.0000 100

  3 omega  -44.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582   77.0000 -120.0000 84

  4 omega  -82.00   16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582  -38.0000 -180.0000 98

  5 omega  -73.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582  133.0000  102.0000 66

  6 omega  -36.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582   38.0000    0.0000 87

  7 omega  -73.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582  133.0000    7.0000 66

  8 omega  -24.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.3082   77.0000    0.0000 107

  9 omega  -24.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.3082   77.0000 -120.0000 112

 10 omega   -9.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.3082 -112.0000  156.0000 68

 11 omega  -55.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582  103.0000 -150.0000 72

 12 omega  -68.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.5582  125.0000  -69.0000 66
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0015347000
_diffrn_orient_matrix_UB_12      -0.0025316000
_diffrn_orient_matrix_UB_13      -0.0548244000
_diffrn_orient_matrix_UB_21      -0.0238739000
_diffrn_orient_matrix_UB_22      -0.0694694000
_diffrn_orient_matrix_UB_23      -0.0237249000
_diffrn_orient_matrix_UB_31      -0.0718794000
_diffrn_orient_matrix_UB_32      0.0017961000
_diffrn_orient_matrix_UB_33      -0.0115508000
_diffrn_radiation_collimation
'multilayer, orthogonal double-bounce X-ray optics'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    K\a
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36338
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.8617
_diffrn_reflns_theta_min         2.1708
_diffrn_source                   'low-power microfocus X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_T_max  1.087
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3284
_exptl_crystal_size_mid          0.2533
_exptl_crystal_size_min          0.1541
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 5512 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.016(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         11751
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.0541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                11065
_reflns_number_total             11751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201328s_si_002.cif
_cod_data_source_block           11jo0008
_cod_original_cell_volume        1303.38(5)
_cod_database_code               1502284
_chemical_oxdiff_formula         'C26 H25 Br N2 O2'
_cell_oxdiff_angle_alpha         111.413(2)
_cell_oxdiff_angle_beta          100.8600(19)
_cell_oxdiff_angle_gamma         101.302(2)
_cell_oxdiff_length_a            9.9605(2)
_cell_oxdiff_length_b            11.4468(3)
_cell_oxdiff_length_c            13.0628(3)
_cell_oxdiff_measurement_reflns_used 23835
_cell_oxdiff_volume              1303.38(5)
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_refine_friedel_coverage         0.88