#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150542.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_7150542
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_formula_sum            'C23 H27 N O3'
_chemical_formula_weight         365.46
_chemical_melting_point          398(3)
_chemical_name_common
;
2-(1',2'-Dihydo-1',1'-dimethylbenzo(c)-quinolinium-2'-yl)-5,5-
dimethyl-1,3-dioxocyclohexan-2-ide
;
_chemical_name_systematic
;
2-(1',2'-Dihydo-1',1'-dimethylbenzo(c)-quinolinium-2'-yl)-
5,5-dimethyl-1,3-dioxocyclohexan-2-ide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.4419(8)
_cell_angle_beta                 91.7559(8)
_cell_angle_gamma                105.0489(8)
_cell_formula_units_Z            2
_cell_length_a                   9.3343(2)
_cell_length_b                   10.2514(2)
_cell_length_c                   11.3449(2)
_cell_measurement_reflns_used    6297
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     942.56(3)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14933
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_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            orange
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                3328
_reflns_number_total             4243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814615b.txt
_cod_data_source_block           c:\xray\compound9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '395-401' was changed to '398(3)' -
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      P-1
_cod_database_code               7150542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.49907(9) 0.89933(9) 0.16960(8) 0.0204(2) Uani 1 1 d . . .
O2 O 0.00383(9) 0.92056(9) 0.20375(8) 0.0216(2) Uani 1 1 d . . .
N1 N 0.17973(11) 0.76631(10) -0.07248(9) 0.0175(2) Uani 1 1 d . . .
C1 C 0.10862(13) 0.49052(13) -0.19166(11) 0.0166(2) Uani 1 1 d . . .
C2 C 0.08703(13) 0.62313(13) -0.18388(11) 0.0169(3) Uani 1 1 d . . .
C3 C -0.01044(14) 0.62418(15) -0.27844(12) 0.0217(3) Uani 1 1 d . . .
C4 C -0.08890(15) 0.48876(15) -0.38327(12) 0.0249(3) Uani 1 1 d . . .
C5 C -0.06860(14) 0.35509(15) -0.39539(12) 0.0231(3) Uani 1 1 d . . .
C6 C 0.02939(14) 0.35664(14) -0.29980(11) 0.0200(3) Uani 1 1 d . . .
C7 C 0.20481(13) 0.49178(12) -0.08510(11) 0.0152(2) Uani 1 1 d . . .
C8 C 0.23389(12) 0.61377(12) 0.03933(11) 0.0150(2) Uani 1 1 d . . .
C9 C 0.30536(13) 0.60545(13) 0.14456(12) 0.0177(3) Uani 1 1 d . . .
C10 C 0.35392(14) 0.48226(13) 0.12533(12) 0.0206(3) Uani 1 1 d . . .
C11 C 0.33496(14) 0.36637(13) 0.00067(12) 0.0204(3) Uani 1 1 d . . .
C12 C 0.26010(13) 0.37147(13) -0.10404(12) 0.0182(3) Uani 1 1 d . . .
C13 C 0.17592(13) 0.74513(12) 0.05827(11) 0.0148(2) Uani 1 1 d . . .
C14 C 0.24384(13) 0.88864(12) 0.18042(11) 0.0152(2) Uani 1 1 d . . .
C15 C 0.39994(13) 0.94737(12) 0.23077(11) 0.0159(2) Uani 1 1 d . . .
C16 C 0.45038(14) 1.07358(13) 0.36908(12) 0.0197(3) Uani 1 1 d . . .
C17 C 0.35748(13) 1.18288(13) 0.41064(11) 0.0184(3) Uani 1 1 d . . .
C18 C 0.19361(13) 1.08942(13) 0.38638(11) 0.0188(3) Uani 1 1 d . . .
C19 C 0.14058(13) 0.96101(12) 0.25015(11) 0.0158(3) Uani 1 1 d . . .
C20 C 0.40726(16) 1.28999(16) 0.55622(13) 0.0270(3) Uani 1 1 d . . .
C21 C 0.37919(16) 1.27378(14) 0.33069(13) 0.0248(3) Uani 1 1 d . . .
C22 C 0.33646(15) 0.80348(15) -0.10332(13) 0.0239(3) Uani 1 1 d . . .
C23 C 0.11995(18) 0.89474(15) -0.05408(13) 0.0269(3) Uani 1 1 d . . .
O3 O 0.78359(12) 1.02828(12) 0.33154(10) 0.0348(3) Uani 1 1 d . . .
H3 H -0.0237(15) 0.7148(16) -0.2721(13) 0.024(3) Uiso 1 1 d . . .
H4 H -0.1600(17) 0.4893(16) -0.4498(14) 0.029(4) Uiso 1 1 d . . .
H5 H -0.1212(15) 0.2610(16) -0.4684(14) 0.022(3) Uiso 1 1 d . . .
H6 H 0.0400(15) 0.2643(16) -0.3070(13) 0.022(3) Uiso 1 1 d . . .
H9 H 0.3164(16) 0.6865(16) 0.2343(14) 0.026(4) Uiso 1 1 d . . .
H10 H 0.4050(16) 0.4777(15) 0.2027(14) 0.025(3) Uiso 1 1 d . . .
H11 H 0.3759(16) 0.2809(17) -0.0140(14) 0.032(4) Uiso 1 1 d . . .
H12 H 0.2450(15) 0.2895(15) -0.1929(13) 0.021(3) Uiso 1 1 d . . .
H13 H 0.0651(14) 0.7131(13) 0.0568(11) 0.011(3) Uiso 1 1 d . . .
H16A H 0.5563(18) 1.1259(16) 0.3815(14) 0.027(4) Uiso 1 1 d . . .
H16B H 0.4457(16) 1.0246(16) 0.4307(15) 0.032(4) Uiso 1 1 d . . .
H18A H 0.1238(15) 1.1519(15) 0.4019(13) 0.021(3) Uiso 1 1 d . . .
H18B H 0.1823(18) 1.0453(18) 0.4521(16) 0.044(4) Uiso 1 1 d . . .
H20A H 0.5140(18) 1.3460(16) 0.5724(14) 0.029(4) Uiso 1 1 d . . .
H20B H 0.3468(18) 1.3608(17) 0.5848(15) 0.037(4) Uiso 1 1 d . . .
H20C H 0.4001(18) 1.2357(18) 0.6104(16) 0.041(4) Uiso 1 1 d . . .
H21A H 0.4878(17) 1.3362(16) 0.3472(13) 0.026(4) Uiso 1 1 d . . .
H21B H 0.3212(18) 1.3477(18) 0.3579(15) 0.039(4) Uiso 1 1 d . . .
H21C H 0.3449(17) 1.2082(17) 0.2327(16) 0.036(4) Uiso 1 1 d . . .
H22A H 0.3310(16) 0.8197(16) -0.1836(15) 0.030(4) Uiso 1 1 d . . .
H22B H 0.3778(16) 0.7178(16) -0.1187(13) 0.029(4) Uiso 1 1 d . . .
H22C H 0.3993(19) 0.8934(19) -0.0298(16) 0.041(4) Uiso 1 1 d . . .
H23A H 0.1284(17) 0.9121(16) -0.1317(15) 0.032(4) Uiso 1 1 d . . .
H23B H 0.0139(18) 0.8698(16) -0.0385(14) 0.028(4) Uiso 1 1 d . . .
H23C H 0.1863(17) 0.9826(17) 0.0243(15) 0.028(4) Uiso 1 1 d . . .
HO3A H 0.695(2) 0.975(2) 0.2765(18) 0.051(5) Uiso 1 1 d . . .
HO3B H 0.857(2) 0.993(2) 0.2958(18) 0.050(5) Uiso 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 0.0033 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'
O O 0.0106 0.0060 '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
C2 N1 C23 111.74(9) . . ?
C2 N1 C22 108.28(9) . . ?
C23 N1 C22 107.83(10) . . ?
C2 N1 C13 108.74(8) . . ?
C23 N1 C13 108.11(9) . . ?
C22 N1 C13 112.18(9) . . ?
C2 C1 C6 117.52(10) . . ?
C2 C1 C7 120.63(10) . . ?
C6 C1 C7 121.75(10) . . ?
C3 C2 C1 121.91(11) . . ?
C3 C2 N1 121.06(10) . . ?
C1 C2 N1 116.96(9) . . ?
C4 C3 C2 118.88(12) . . ?
C5 C4 C3 120.85(11) . . ?
C4 C5 C6 119.30(12) . . ?
C5 C6 C1 121.52(12) . . ?
C12 C7 C8 119.82(10) . . ?
C12 C7 C1 121.50(10) . . ?
C8 C7 C1 118.59(10) . . ?
C9 C8 C7 118.80(10) . . ?
C9 C8 C13 121.59(10) . . ?
C7 C8 C13 119.42(10) . . ?
C10 C9 C8 120.55(11) . . ?
C9 C10 C11 120.68(11) . . ?
C12 C11 C10 119.18(11) . . ?
C11 C12 C7 120.67(11) . . ?
H13 C13 C14 108.2(7) . . ?
H13 C13 C8 108.3(7) . . ?
C14 C13 C8 117.05(9) . . ?
H13 C13 N1 99.8(7) . . ?
C14 C13 N1 113.67(9) . . ?
C8 C13 N1 108.30(9) . . ?
C15 C14 C19 120.40(10) . . ?
C15 C14 C13 123.49(10) . . ?
C19 C14 C13 116.01(10) . . ?
O1 C15 C14 124.15(10) . . ?
O1 C15 C16 117.59(10) . . ?
C14 C15 C16 118.23(10) . . ?
C15 C16 C17 115.28(9) . . ?
C16 C17 C18 107.05(9) . . ?
C16 C17 C20 109.44(10) . . ?
C18 C17 C20 110.18(10) . . ?
C16 C17 C21 110.14(10) . . ?
C18 C17 C21 110.73(10) . . ?
C20 C17 C21 109.28(10) . . ?
C19 C18 C17 114.48(10) . . ?
O2 C19 C14 122.37(10) . . ?
O2 C19 C18 117.54(10) . . ?
C14 C19 C18 120.08(10) . . ?
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
O1 C15 1.2544(14) . ?
O2 C19 1.2577(14) . ?
N1 C2 1.4962(14) . ?
N1 C23 1.4999(15) . ?
N1 C22 1.5034(17) . ?
N1 C13 1.5857(14) . ?
C1 C2 1.3931(16) . ?
C1 C6 1.3998(17) . ?
C1 C7 1.4773(15) . ?
C2 C3 1.3905(16) . ?
C3 C4 1.3894(18) . ?
C4 C5 1.3831(19) . ?
C5 C6 1.3894(18) . ?
C7 C12 1.3971(16) . ?
C7 C8 1.4034(16) . ?
C8 C9 1.3938(16) . ?
C8 C13 1.5161(15) . ?
C9 C10 1.3868(17) . ?
C10 C11 1.3885(17) . ?
C11 C12 1.3862(17) . ?
C13 H13 0.998(12) . ?
C13 C14 1.5038(15) . ?
C14 C15 1.4215(16) . ?
C14 C19 1.4274(15) . ?
C15 C16 1.5219(16) . ?
C16 C17 1.5239(16) . ?
C17 C18 1.5259(17) . ?
C17 C20 1.5286(17) . ?
C17 C21 1.5313(18) . ?
C18 C19 1.5159(16) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 N1 C2 C3 17.82(15) . . . . ?
C22 N1 C2 C1 76.12(12) . . . . ?
C14 C13 C8 C9 21.36(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190110
