A Facile, Metal- and Solvent Free, Autoxidative Coupling of Quinolines with Indoles and Pyrroles
Mikael Brasse; Jonathan Ellman; Robert Bergman; Chem.Commun. 47 (2011) 5019–; doi:10.1039/c1cc10507h

data_7106301
_publ_section_title
;
 A Facile, Metal- and Solvent Free, Autoxidative Coupling of Quinolines
 with Indoles and Pyrroles
;
_journal_name_full               Chem.Commun.
_journal_page_first              5019
_journal_paper_doi               10.1039/c1cc10507h
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C22 H16 Cl2 N2'
_chemical_formula_weight         379.27
_chemical_name_common            MB-II-194
_chemical_name_systematic
;
bergman05
;
_space_group.centring_type       P
_space_group_IT_number           14
_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                 97.850(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5493(10)
_cell_length_b                   9.3890(11)
_cell_length_c                   22.288(2)
_cell_measurement_reflns_used    9424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.62
_cell_measurement_theta_min      5.12
_cell_volume                     1772.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2008
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22240
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.04
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_T_max  0.8779
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0670P)^2^+0.4411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2795
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10507h.txt
_cod_data_source_block           bergman05
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        1772.3(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7106301