#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/63/7106301.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7106301
loop_
_publ_author_name
'Mikael Brasse'
'Jonathan Ellman'
'Robert Bergman'
_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/[σ²(Fo²)+(0.0670P)²+0.4411P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1585(2) 0.3162(2) 0.73921(8) 0.0239(4) Uani 1 1 d . . .
H1 H 0.0617 0.3595 0.7456 0.029 Uiso 1 1 calc R . .
C2 C 0.1762(2) 0.22143(19) 0.69339(8) 0.0216(4) Uani 1 1 d . . .
C3 C 0.3419(2) 0.1838(2) 0.70033(8) 0.0221(4) Uani 1 1 d . . .
C4 C 0.4355(2) 0.0982(2) 0.66811(8) 0.0248(4) Uani 1 1 d . . .
H4 H 0.3893 0.0464 0.6336 0.030 Uiso 1 1 calc R . .
C5 C 0.5960(2) 0.0902(2) 0.68716(8) 0.0280(4) Uani 1 1 d . . .
H5 H 0.6598 0.0318 0.6656 0.034 Uiso 1 1 calc R . .
C6 C 0.6667(2) 0.1673(2) 0.73805(8) 0.0300(4) Uani 1 1 d . . .
H6 H 0.7773 0.1597 0.7502 0.036 Uiso 1 1 calc R . .
C7 C 0.5777(2) 0.2536(2) 0.77046(8) 0.0281(4) Uani 1 1 d . . .
H7 H 0.6252 0.3063 0.8046 0.034 Uiso 1 1 calc R . .
C8 C 0.4151(2) 0.2608(2) 0.75124(8) 0.0242(4) Uani 1 1 d . . .
C9 C 0.0550(2) 0.1646(2) 0.64593(7) 0.0218(4) Uani 1 1 d . . .
C10 C -0.0755(2) 0.2513(2) 0.61742(8) 0.0219(4) Uani 1 1 d . . .
C11 C -0.0937(2) 0.3958(2) 0.63193(8) 0.0246(4) Uani 1 1 d . . .
H11 H -0.0173 0.4402 0.6609 0.029 Uiso 1 1 calc R . .
C12 C -0.2202(2) 0.4738(2) 0.60486(9) 0.0290(4) Uani 1 1 d . . .
H12 H -0.2311 0.5711 0.6152 0.035 Uiso 1 1 calc R . .
C13 C -0.3324(2) 0.4089(2) 0.56219(8) 0.0320(5) Uani 1 1 d . . .
H13 H -0.4210 0.4622 0.5441 0.038 Uiso 1 1 calc R . .
C14 C -0.3163(2) 0.2694(2) 0.54603(8) 0.0288(4) Uani 1 1 d . . .
H14 H -0.3930 0.2278 0.5163 0.035 Uiso 1 1 calc R . .
C15 C -0.1876(2) 0.1868(2) 0.57289(7) 0.0237(4) Uani 1 1 d . . .
C16 C -0.1637(2) 0.0408(2) 0.55609(7) 0.0236(4) Uani 1 1 d . . .
C17 C -0.2644(2) -0.0348(2) 0.51127(8) 0.0283(4) Uani 1 1 d . . .
H17 H -0.3564 0.0107 0.4914 0.034 Uiso 1 1 calc R . .
C18 C -0.2323(2) -0.1713(2) 0.49601(8) 0.0307(4) Uani 1 1 d . . .
H18 H -0.3017 -0.2193 0.4657 0.037 Uiso 1 1 calc R . .
C19 C -0.0971(2) -0.2415(2) 0.52480(8) 0.0288(4) Uani 1 1 d . . .
H19 H -0.0748 -0.3364 0.5139 0.035 Uiso 1 1 calc R . .
C20 C 0.0026(2) -0.1716(2) 0.56894(8) 0.0275(4) Uani 1 1 d . . .
H20 H 0.0936 -0.2189 0.5887 0.033 Uiso 1 1 calc R . .
C21 C -0.0292(2) -0.0307(2) 0.58500(8) 0.0232(4) Uani 1 1 d . . .
C22 C 0.5964(3) 0.4343(2) 0.34934(9) 0.0353(5) Uani 1 1 d . . .
H22A H 0.6477 0.4169 0.3128 0.042 Uiso 1 1 calc R . .
H22B H 0.5122 0.5061 0.3390 0.042 Uiso 1 1 calc R . .
N1 N 0.30034(19) 0.33881(18) 0.77416(7) 0.0251(3) Uani 1 1 d . . .
H1A H 0.3160 0.3944 0.8062 0.030 Uiso 1 1 calc R . .
N2 N 0.07575(18) 0.03242(17) 0.63021(6) 0.0225(3) Uani 1 1 d . . .
Cl1 Cl 0.73698(6) 0.50031(6) 0.40795(2) 0.03707(16) Uani 1 1 d . . .
Cl2 Cl 0.51181(6) 0.27301(5) 0.37188(2) 0.03286(15) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.15(17) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C1 C2 C3 106.44(15) . . ?
C1 C2 C9 128.86(17) . . ?
C3 C2 C9 124.70(16) . . ?
C4 C3 C8 118.90(17) . . ?
C4 C3 C2 134.83(16) . . ?
C8 C3 C2 106.22(16) . . ?
C5 C4 C3 119.13(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.20(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.02(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 117.60(17) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C7 129.81(17) . . ?
N1 C8 C3 108.05(16) . . ?
C7 C8 C3 122.13(18) . . ?
N2 C9 C10 122.52(16) . . ?
N2 C9 C2 115.31(16) . . ?
C10 C9 C2 122.14(17) . . ?
C11 C10 C15 119.13(17) . . ?
C11 C10 C9 122.74(16) . . ?
C15 C10 C9 118.13(17) . . ?
C12 C11 C10 121.13(18) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.80(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.95(18) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 118.40(18) . . ?
C14 C15 C16 122.83(17) . . ?
C10 C15 C16 118.76(16) . . ?
C21 C16 C17 117.59(18) . . ?
C21 C16 C15 117.99(16) . . ?
C17 C16 C15 124.39(17) . . ?
C18 C17 C16 121.54(18) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.50(17) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.48(19) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.52(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
N2 C21 C20 117.26(17) . . ?
N2 C21 C16 122.38(18) . . ?
C20 C21 C16 120.36(17) . . ?
Cl1 C22 Cl2 110.63(11) . . ?
Cl1 C22 H22A 109.5 . . ?
Cl2 C22 H22A 109.5 . . ?
Cl1 C22 H22B 109.5 . . ?
Cl2 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C1 N1 C8 109.13(15) . . ?
C1 N1 H1A 125.4 . . ?
C8 N1 H1A 125.4 . . ?
C9 N2 C21 120.11(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.365(2) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.448(3) . ?
C2 C9 1.476(2) . ?
C3 C4 1.399(3) . ?
C3 C8 1.417(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.377(3) . ?
C9 N2 1.308(3) . ?
C9 C10 1.455(2) . ?
C10 C11 1.408(3) . ?
C10 C15 1.418(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.411(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.443(3) . ?
C16 C21 1.409(3) . ?
C16 C17 1.417(3) . ?
C17 C18 1.363(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.407(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(3) . ?
C20 H20 0.9500 . ?
C21 N2 1.387(2) . ?
C22 Cl1 1.762(2) . ?
C22 Cl2 1.780(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N1 H1A 0.8800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653277
2 PubChem 139181841
