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#$Date: 2022-03-04 02:24:26 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273300 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566550.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_1566550
loop_
_publ_author_name
'Wittmann, Christopher'
'Bacher, Felix'
'Enyedy, Eva A.'
'Dömötör, Orsolya'
'Spengler, Gabriella'
'Madejski, Christian'
'Reynisson, Jóhannes'
'Arion, Vladimir B.'
_publ_section_title
;
 Highly Antiproliferative Latonduine and Indolo[2,3-c]quinoline
 Derivatives: Complex Formation with Copper(II) Markedly Changes the
 Kinase Inhibitory Profile.
;
_journal_issue                   3
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2238
_journal_page_last               2261
_journal_paper_doi               10.1021/acs.jmedchem.1c01740
_journal_volume                  65
_journal_year                    2022
_chemical_formula_moiety         'C12 H16 N2 O2'
_chemical_formula_sum            'C12 H16 N2 O2'
_chemical_formula_weight         220.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                99.872(4)
_cell_angle_beta                 102.594(4)
_cell_angle_gamma                113.640(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7366(8)
_cell_length_b                   7.9072(8)
_cell_length_c                   10.7395(11)
_cell_measurement_reflns_used    2988
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.003
_cell_measurement_theta_min      2.938
_cell_volume                     562.21(10)
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         2.030
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+0.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             3285
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jm1c01740_si_012.cif
_cod_data_source_block           chwi398
_cod_database_code               1566550
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.28445(14) 0.30911(13) 0.02347(9) 0.0205(2) Uani 1 1 d . . . . .
C2 C 0.28681(15) 0.16800(15) 0.07645(11) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.30645(16) 0.18010(16) 0.21048(11) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.3075 0.0771 0.2444 0.025 Uiso 1 1 calc R U . . .
C4 C 0.32434(16) 0.34553(16) 0.29280(11) 0.0214(2) Uani 1 1 d . . . . .
H4 H 0.3363 0.3570 0.3842 0.026 Uiso 1 1 calc R U . . .
C5 C 0.32457(15) 0.49495(15) 0.24040(11) 0.0185(2) Uani 1 1 d . . . . .
C6 C 0.30371(16) 0.46853(15) 0.10533(11) 0.0204(2) Uani 1 1 d . . . . .
H6 H 0.3031 0.5698 0.0690 0.024 Uiso 1 1 calc R U . . .
C7 C 0.26585(16) -0.00997(16) -0.01636(11) 0.0212(2) Uani 1 1 d . . . . .
C8 C 0.23937(19) -0.01770(17) -0.15972(12) 0.0265(3) Uani 1 1 d . . . . .
H8A H 0.3624 0.0770 -0.1677 0.040 Uiso 1 1 calc R U . . .
H8B H 0.1301 0.0120 -0.1944 0.040 Uiso 1 1 calc R U . . .
H8C H 0.2082 -0.1472 -0.2110 0.040 Uiso 1 1 calc R U . . .
O9 O 0.27218(14) -0.14110(12) 0.02654(9) 0.0302(2) Uani 1 1 d . . . . .
C10 C 0.34445(15) 0.67805(15) 0.32666(11) 0.0199(2) Uani 1 1 d . . . . .
H10A H 0.4575 0.7267 0.4097 0.024 Uiso 1 1 calc R U . . .
H10B H 0.3729 0.7776 0.2789 0.024 Uiso 1 1 calc R U . . .
N11 N 0.16190(13) 0.64452(12) 0.36018(9) 0.01744(19) Uani 1 1 d . . . . .
C12 C 0.19328(16) 0.81133(15) 0.46288(10) 0.0204(2) Uani 1 1 d . . . . .
H12A H 0.2350 0.9269 0.4306 0.024 Uiso 1 1 calc R U . . .
H12B H 0.3004 0.8365 0.5441 0.024 Uiso 1 1 calc R U . . .
C13 C 0.00262(17) 0.77298(16) 0.49579(11) 0.0226(2) Uani 1 1 d . . . . .
H13A H -0.0351 0.6610 0.5319 0.027 Uiso 1 1 calc R U . . .
H13B H 0.0251 0.8864 0.5652 0.027 Uiso 1 1 calc R U . . .
O14 O -0.15609(12) 0.73479(11) 0.38049(8) 0.0247(2) Uani 1 1 d . . . . .
C15 C -0.18760(16) 0.57246(16) 0.27893(12) 0.0236(2) Uani 1 1 d . . . . .
H15A H -0.2962 0.5479 0.1988 0.028 Uiso 1 1 calc R U . . .
H15B H -0.2291 0.4567 0.3110 0.028 Uiso 1 1 calc R U . . .
C16 C -0.00133(15) 0.60628(15) 0.24196(11) 0.0193(2) Uani 1 1 d . . . . .
H16A H -0.0269 0.4913 0.1726 0.023 Uiso 1 1 calc R U . . .
H16B H 0.0366 0.7176 0.2051 0.023 Uiso 1 1 calc R U . . .
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
C6 N1 C2 117.25(9) . . ?
N1 C2 C3 123.14(9) . . ?
N1 C2 C7 116.75(9) . . ?
C3 C2 C7 120.11(9) . . ?
C4 C3 C2 118.54(10) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.37(10) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 117.64(10) . . ?
C6 C5 C10 121.23(9) . . ?
C4 C5 C10 121.12(10) . . ?
N1 C6 C5 124.05(10) . . ?
N1 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
O9 C7 C8 122.24(10) . . ?
O9 C7 C2 119.86(10) . . ?
C8 C7 C2 117.90(9) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N11 C10 C5 111.05(8) . . ?
N11 C10 H10A 109.4 . . ?
C5 C10 H10A 109.4 . . ?
N11 C10 H10B 109.4 . . ?
C5 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 N11 C10 110.93(8) . . ?
C12 N11 C16 108.79(8) . . ?
C10 N11 C16 110.94(8) . . ?
N11 C12 C13 109.89(9) . . ?
N11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O14 C13 C12 111.31(9) . . ?
O14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 O14 C15 109.68(8) . . ?
O14 C15 C16 111.44(9) . . ?
O14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N11 C16 C15 109.99(9) . . ?
N11 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N11 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
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
N1 C6 1.3403(13) . ?
N1 C2 1.3410(13) . ?
C2 C3 1.3964(15) . ?
C2 C7 1.5052(15) . ?
C3 C4 1.3845(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3926(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3931(15) . ?
C5 C10 1.5091(14) . ?
C6 H6 0.9500 . ?
C7 O9 1.2184(13) . ?
C7 C8 1.4954(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 N11 1.4658(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 C12 1.4638(13) . ?
N11 C16 1.4701(13) . ?
C12 C13 1.5159(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.4295(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O14 C15 1.4317(13) . ?
C15 C16 1.5108(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O9 0.95 2.50 3.4224(13) 164.3 1_565
C13 H13B O14 0.99 2.65 3.4867(14) 141.8 2_576
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
C6 N1 C2 C3 0.55(15) . . . . ?
C6 N1 C2 C7 -179.77(9) . . . . ?
N1 C2 C3 C4 0.01(16) . . . . ?
C7 C2 C3 C4 -179.66(9) . . . . ?
C2 C3 C4 C5 -0.73(15) . . . . ?
C3 C4 C5 C6 0.87(15) . . . . ?
C3 C4 C5 C10 -179.79(9) . . . . ?
C2 N1 C6 C5 -0.39(15) . . . . ?
C4 C5 C6 N1 -0.31(16) . . . . ?
C10 C5 C6 N1 -179.65(9) . . . . ?
N1 C2 C7 O9 178.06(10) . . . . ?
C3 C2 C7 O9 -2.25(16) . . . . ?
N1 C2 C7 C8 -1.43(14) . . . . ?
C3 C2 C7 C8 178.26(10) . . . . ?
C6 C5 C10 N11 107.17(11) . . . . ?
C4 C5 C10 N11 -72.15(12) . . . . ?
C5 C10 N11 C12 169.57(8) . . . . ?
C5 C10 N11 C16 -69.39(11) . . . . ?
C10 N11 C12 C13 -179.95(8) . . . . ?
C16 N11 C12 C13 57.75(11) . . . . ?
N11 C12 C13 O14 -59.01(11) . . . . ?
C12 C13 O14 C15 58.24(11) . . . . ?
C13 O14 C15 C16 -58.13(12) . . . . ?
C12 N11 C16 C15 -57.63(11) . . . . ?
C10 N11 C16 C15 -179.93(8) . . . . ?
O14 C15 C16 N11 58.55(12) . . . . ?
