#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:10:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180291 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150541.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_7150541
loop_
_publ_author_name
'O'Leary, Jane'
'Wallis, John D.'
_publ_section_title
;
 Interactions and reactions in some 2,2′-disubstituted
 biphenyls---an open or shut case
;
_journal_issue                   2
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              225
_journal_page_last               228
_journal_paper_doi               10.1039/b814615b
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H15 N3'
_chemical_formula_sum            'C18 H15 N3'
_chemical_formula_weight         273.33
_chemical_melting_point          93.0(10)
_chemical_name_common
;5-(1,2-Dihydro-1,1-dimethylbenzo(c)quinolinium-2-yl) -
dicyanomethide
;
_chemical_name_systematic
;
5-(1,2-Dihydro-1,1-dimethylbenzo(c)quinolinium-2-yl)
-dicyanomethide
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.1420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4599(4)
_cell_length_b                   8.2053(3)
_cell_length_c                   14.7752(7)
_cell_measurement_reflns_used    8822
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1388.37(10)
_computing_cell_refinement
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10933
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
using multiple and symmetry-related data measurements via the
program SORTAV (Blessing, 1995)
See R.H. Blessing, Acta Cryst., (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0465
_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)+(0.0602P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                4750
_reflns_number_total             5657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814615b.txt
_cod_data_source_block           d:\biphen_compound8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '92-94' was changed to '93.0(10)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7150541
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
N1A N 0.21299(14) 0.70104(19) 0.76413(11) 0.0182(4) Uani 1 1 d . . .
N2A N 0.34773(17) 0.4594(2) 0.52226(13) 0.0299(5) Uani 1 1 d . . .
N3A N 0.07572(16) 0.2411(2) 0.68856(14) 0.0337(5) Uani 1 1 d . . .
C1A C 0.37818(17) 0.7836(2) 0.67242(13) 0.0187(4) Uani 1 1 d . . .
C2A C 0.34106(17) 0.7059(2) 0.75103(13) 0.0179(4) Uani 1 1 d . . .
C3A C 0.41847(18) 0.6346(3) 0.81255(14) 0.0237(5) Uani 1 1 d . . .
H3A H 0.3912 0.5859 0.8661 0.028 Uiso 1 1 calc R . .
C4A C 0.53689(19) 0.6347(3) 0.79540(16) 0.0274(5) Uani 1 1 d . . .
H4A H 0.5913 0.5858 0.8372 0.033 Uiso 1 1 calc R . .
C5A C 0.57517(19) 0.7066(3) 0.71682(16) 0.0281(5) Uani 1 1 d . . .
H5A H 0.6559 0.7048 0.7045 0.034 Uiso 1 1 calc R . .
C6A C 0.49763(18) 0.7804(2) 0.65657(15) 0.0230(5) Uani 1 1 d . . .
H6A H 0.5256 0.8299 0.6034 0.028 Uiso 1 1 calc R . .
C7A C 0.29123(17) 0.8577(2) 0.60862(13) 0.0186(4) Uani 1 1 d . . .
C8A C 0.17675(18) 0.7988(2) 0.60733(13) 0.0187(4) Uani 1 1 d . . .
C9A C 0.09019(18) 0.8705(2) 0.55213(13) 0.0220(5) Uani 1 1 d . . .
H9A H 0.0126 0.8296 0.5516 0.026 Uiso 1 1 calc R . .
C10A C 0.1175(2) 1.0020(3) 0.49790(14) 0.0265(5) Uani 1 1 d . . .
H10A H 0.0587 1.0516 0.4602 0.032 Uiso 1 1 calc R . .
C11A C 0.2313(2) 1.0612(3) 0.49875(14) 0.0276(5) Uani 1 1 d . . .
H11A H 0.2496 1.1513 0.4615 0.033 Uiso 1 1 calc R . .
C12A C 0.31758(19) 0.9907(3) 0.55290(13) 0.0244(5) Uani 1 1 d . . .
H12A H 0.3950 1.0319 0.5527 0.029 Uiso 1 1 calc R . .
C13A C 0.14912(18) 0.6587(2) 0.66852(13) 0.0179(4) Uani 1 1 d . . .
H13A H 0.0656(18) 0.658(2) 0.6868(13) 0.018(5) Uiso 1 1 d . . .
C14A C 0.18259(17) 0.4952(2) 0.63354(13) 0.0180(4) Uani 1 1 d . . .
C15A C 0.27324(18) 0.4760(2) 0.57296(13) 0.0203(4) Uani 1 1 d . . .
C16A C 0.12416(18) 0.3555(2) 0.66228(14) 0.0231(5) Uani 1 1 d . . .
C17A C 0.16652(18) 0.8617(2) 0.79687(14) 0.0241(5) Uani 1 1 d . . .
H17U H 0.0822 0.8528 0.8045 0.036 Uiso 1 1 calc R . .
H17V H 0.1820 0.9468 0.7524 0.036 Uiso 1 1 calc R . .
H17W H 0.2052 0.8898 0.8551 0.036 Uiso 1 1 calc R . .
C18A C 0.17956(18) 0.5748(2) 0.83224(14) 0.0239(5) Uani 1 1 d . . .
H18U H 0.0947 0.5760 0.8384 0.036 Uiso 1 1 calc R . .
H18V H 0.2182 0.5992 0.8910 0.036 Uiso 1 1 calc R . .
H18W H 0.2040 0.4668 0.8118 0.036 Uiso 1 1 calc R . .
N1B N 0.24624(14) 0.66512(19) 0.27248(11) 0.0181(4) Uani 1 1 d . . .
N2B N 0.11270(16) 1.1354(2) 0.22915(13) 0.0277(4) Uani 1 1 d . . .
N3B N 0.29921(17) 0.9087(2) 0.00574(13) 0.0307(5) Uani 1 1 d . . .
C1B C 0.37880(17) 0.5715(2) 0.15599(13) 0.0186(4) Uani 1 1 d . . .
C2B C 0.36703(17) 0.6515(2) 0.23905(13) 0.0183(4) Uani 1 1 d . . .
C3B C 0.46198(18) 0.7156(2) 0.28743(15) 0.0226(4) Uani 1 1 d . . .
H3B H 0.4520 0.7676 0.3441 0.027 Uiso 1 1 calc R . .
C4B C 0.57201(19) 0.7029(3) 0.25208(15) 0.0270(5) Uani 1 1 d . . .
H4B H 0.6379 0.7470 0.2844 0.032 Uiso 1 1 calc R . .
C5B C 0.58585(18) 0.6260(3) 0.16988(15) 0.0260(5) Uani 1 1 d . . .
H5B H 0.6613 0.6184 0.1458 0.031 Uiso 1 1 calc R . .
C6B C 0.49128(17) 0.5604(2) 0.12272(14) 0.0221(5) Uani 1 1 d . . .
H6B H 0.5025 0.5069 0.0667 0.027 Uiso 1 1 calc R . .
C7B C 0.27487(17) 0.5064(2) 0.10625(12) 0.0178(4) Uani 1 1 d . . .
C8B C 0.16594(17) 0.5771(2) 0.12242(13) 0.0170(4) Uani 1 1 d . . .
C9B C 0.06608(18) 0.5194(2) 0.07788(13) 0.0200(4) Uani 1 1 d . . .
H9B H -0.0070 0.5691 0.0886 0.024 Uiso 1 1 calc R . .
C10B C 0.07100(18) 0.3897(2) 0.01774(14) 0.0224(5) Uani 1 1 d . . .
H10B H 0.0021 0.3512 -0.0130 0.027 Uiso 1 1 calc R . .
C11B C 0.17838(19) 0.3171(2) 0.00312(14) 0.0225(5) Uani 1 1 d . . .
H11B H 0.1825 0.2269 -0.0369 0.027 Uiso 1 1 calc R . .
C12B C 0.27896(18) 0.3751(2) 0.04630(13) 0.0206(4) Uani 1 1 d . . .
H12B H 0.3518 0.3251 0.0351 0.025 Uiso 1 1 calc R . .
C13B C 0.16056(17) 0.7146(2) 0.19025(14) 0.0171(4) Uani 1 1 d . . .
H13B H 0.0860(17) 0.714(2) 0.2201(13) 0.014(5) Uiso 1 1 d . . .
C14B C 0.18668(17) 0.8772(2) 0.15151(13) 0.0183(4) Uani 1 1 d . . .
C15B C 0.14629(17) 1.0191(2) 0.19285(14) 0.0206(4) Uani 1 1 d . . .
C16B C 0.24903(18) 0.8939(2) 0.07204(14) 0.0202(4) Uani 1 1 d . . .
C17B C 0.20460(19) 0.5065(2) 0.31231(13) 0.0237(5) Uani 1 1 d . . .
H17X H 0.1253 0.5207 0.3337 0.035 Uiso 1 1 calc R . .
H17Y H 0.2570 0.4749 0.3632 0.035 Uiso 1 1 calc R . .
H17Z H 0.2045 0.4213 0.2658 0.035 Uiso 1 1 calc R . .
C18B C 0.2368(2) 0.7918(3) 0.34504(14) 0.0249(5) Uani 1 1 d . . .
H18X H 0.1563 0.7960 0.3650 0.037 Uiso 1 1 calc R . .
H18Y H 0.2587 0.8984 0.3210 0.037 Uiso 1 1 calc R . .
H18Z H 0.2894 0.7636 0.3965 0.037 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 '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
C2A N1A C18A 112.50(15) . . ?
C2A N1A C17A 112.33(15) . . ?
C18A N1A C17A 106.59(14) . . ?
C2A N1A C13A 108.12(14) . . ?
C18A N1A C13A 108.72(15) . . ?
C17A N1A C13A 108.46(15) . . ?
C6A C1A C2A 117.31(18) . . ?
C6A C1A C7A 122.85(18) . . ?
C2A C1A C7A 119.78(17) . . ?
C3A C2A C1A 122.09(18) . . ?
C3A C2A N1A 121.13(17) . . ?
C1A C2A N1A 116.77(17) . . ?
C2A C3A C4A 119.3(2) . . ?
C5A C4A C3A 119.6(2) . . ?
C6A C5A C4A 120.81(19) . . ?
C5A C6A C1A 120.88(19) . . ?
C8A C7A C12A 118.85(19) . . ?
C8A C7A C1A 118.47(17) . . ?
C12A C7A C1A 122.59(18) . . ?
C9A C8A C7A 120.66(18) . . ?
C9A C8A C13A 120.96(18) . . ?
C7A C8A C13A 118.37(18) . . ?
C10A C9A C8A 119.75(19) . . ?
C9A C10A C11A 119.9(2) . . ?
C12A C11A C10A 120.80(19) . . ?
C11A C12A C7A 120.1(2) . . ?
C14A C13A C8A 114.59(16) . . ?
C14A C13A N1A 112.61(16) . . ?
C8A C13A N1A 105.35(15) . . ?
C16A C14A C15A 118.27(17) . . ?
C16A C14A C13A 119.90(16) . . ?
C15A C14A C13A 121.82(17) . . ?
N2A C15A C14A 179.5(2) . . ?
N3A C16A C14A 178.1(2) . . ?
C2B N1B C18B 112.40(16) . . ?
C2B N1B C17B 112.01(14) . . ?
C18B N1B C17B 106.61(14) . . ?
C2B N1B C13B 108.73(14) . . ?
C18B N1B C13B 108.13(14) . . ?
C17B N1B C13B 108.84(15) . . ?
C6B C1B C2B 117.22(18) . . ?
C6B C1B C7B 122.58(17) . . ?
C2B C1B C7B 120.19(17) . . ?
C3B C2B C1B 122.05(18) . . ?
C3B C2B N1B 121.49(18) . . ?
C1B C2B N1B 116.46(17) . . ?
C2B C3B C4B 119.0(2) . . ?
C5B C4B C3B 120.1(2) . . ?
C6B C5B C4B 120.6(2) . . ?
C5B C6B C1B 121.02(19) . . ?
C12B C7B C8B 118.52(18) . . ?
C12B C7B C1B 123.32(17) . . ?
C8B C7B C1B 118.13(17) . . ?
C9B C8B C7B 120.18(18) . . ?
C9B C8B C13B 121.18(17) . . ?
C7B C8B C13B 118.64(17) . . ?
C8B C9B C10B 120.96(18) . . ?
C9B C10B C11B 119.00(19) . . ?
C12B C11B C10B 120.56(19) . . ?
C11B C12B C7B 120.77(18) . . ?
C14B C13B C8B 113.63(16) . . ?
C14B C13B N1B 113.39(16) . . ?
C8B C13B N1B 106.09(15) . . ?
C15B C14B C16B 118.03(18) . . ?
C15B C14B C13B 120.22(16) . . ?
C16B C14B C13B 121.73(17) . . ?
N2B C15B C14B 178.4(2) . . ?
N3B C16B C14B 179.0(2) . . ?
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
N1A C2A 1.488(2) . ?
N1A C18A 1.504(2) . ?
N1A C17A 1.508(2) . ?
N1A C13A 1.604(3) . ?
N2A C15A 1.164(3) . ?
N3A C16A 1.164(3) . ?
C1A C6A 1.398(3) . ?
C1A C2A 1.405(3) . ?
C1A C7A 1.477(3) . ?
C2A C3A 1.377(3) . ?
C3A C4A 1.390(3) . ?
C4A C5A 1.388(3) . ?
C5A C6A 1.375(3) . ?
C7A C8A 1.398(3) . ?
C7A C12A 1.406(3) . ?
C8A C9A 1.391(3) . ?
C8A C13A 1.503(3) . ?
C9A C10A 1.387(3) . ?
C10A C11A 1.390(3) . ?
C11A C12A 1.376(3) . ?
C13A C14A 1.493(3) . ?
C14A C16A 1.402(3) . ?
C14A C15A 1.405(3) . ?
N1B C2B 1.491(2) . ?
N1B C18B 1.500(2) . ?
N1B C17B 1.513(2) . ?
N1B C13B 1.586(3) . ?
N2B C15B 1.167(3) . ?
N3B C16B 1.161(3) . ?
C1B C6B 1.400(3) . ?
C1B C2B 1.403(3) . ?
C1B C7B 1.476(3) . ?
C2B C3B 1.383(3) . ?
C3B C4B 1.387(3) . ?
C4B C5B 1.383(3) . ?
C5B C6B 1.376(3) . ?
C7B C12B 1.396(3) . ?
C7B C8B 1.405(3) . ?
C8B C9B 1.382(3) . ?
C8B C13B 1.512(3) . ?
C9B C10B 1.389(3) . ?
C10B C11B 1.391(3) . ?
C11B C12B 1.381(3) . ?
C13B C14B 1.487(3) . ?
C14B C15B 1.402(3) . ?
C14B C16B 1.404(3) . ?
