#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/44/4314478.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_4314478
loop_
_publ_author_name
'Michael F. Primik'
'Gerhard Mühlgassner'
'Michael A. Jakupec'
'Olivier Zava'
'Paul J. Dyson'
'Vladimir B. Arion'
'Bernhard K. Keppler'
_publ_section_title
;
 Highly Cytotoxic Copper(II) Complexes with Modified Paullone Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              302
_journal_page_last               311
_journal_paper_doi               10.1021/ic902042a
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C22 H16 Br N5, 2(C H4 O)'
_chemical_formula_sum            'C24 H24 Br N5 O2'
_chemical_formula_weight         494.39
_chemical_name_systematic
; 
N-(9-Bromo-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5H)-yliden)-N'-
(1-pyridin-2-yl-methylidene)-azine dimethanol solvate  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 97.995(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3094(5)
_cell_length_b                   11.1450(4)
_cell_length_c                   17.0199(7)
_cell_measurement_reflns_used    1293
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.56
_cell_measurement_theta_min      2.41
_cell_volume                     2312.24(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            104909
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  0.8398
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0650
_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)+(0.0899P)²+7.2173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.1932
_reflns_number_gt                3320
_reflns_number_total             4304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902042a_si_002_3.cif
_cod_data_source_block           mipr033
_cod_database_code               4314478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 1.08790(6) 0.59566(7) 0.13678(5) 0.0825(4) Uani 1 1 d . . .
N5 N 0.5147(3) 0.9387(3) 0.12107(19) 0.0221(7) Uani 1 1 d . . .
H5 H 0.4481 0.9156 0.1013 0.027 Uiso 1 1 calc R . .
N12 N 0.7579(3) 0.8389(3) 0.3095(2) 0.0242(7) Uani 1 1 d . . .
H12 H 0.7428 0.8361 0.3585 0.029 Uiso 1 1 calc R . .
N13 N 0.5788(3) 0.8489(3) 0.0108(2) 0.0255(8) Uani 1 1 d . . .
N14 N 0.4700(3) 0.8113(3) -0.0090(2) 0.0267(8) Uani 1 1 d . . .
N17 N 0.2635(3) 0.7194(4) -0.0623(2) 0.0368(9) Uani 1 1 d . . .
C1 C 0.6024(4) 1.0433(4) 0.3290(3) 0.0290(10) Uani 1 1 d . . .
H1 H 0.6603 1.0339 0.3717 0.035 Uiso 1 1 calc R . .
C2 C 0.5145(4) 1.1146(4) 0.3393(3) 0.0338(11) Uani 1 1 d . . .
H2 H 0.5123 1.1547 0.3883 0.041 Uiso 1 1 calc R . .
C3 C 0.4289(4) 1.1277(4) 0.2777(3) 0.0320(10) Uani 1 1 d . . .
H3 H 0.3671 1.1755 0.2848 0.038 Uiso 1 1 calc R . .
C4 C 0.4335(4) 1.0713(4) 0.2058(3) 0.0261(9) Uani 1 1 d . . .
H4 H 0.3750 1.0815 0.1636 0.031 Uiso 1 1 calc R . .
C4A C 0.5233(3) 0.9995(3) 0.1943(2) 0.0212(8) Uani 1 1 d . . .
C6 C 0.5949(3) 0.9107(3) 0.0769(2) 0.0211(8) Uani 1 1 d . . .
C7 C 0.7090(3) 0.9513(4) 0.1046(2) 0.0239(9) Uani 1 1 d . . .
H7A H 0.7568 0.9313 0.0643 0.029 Uiso 1 1 calc R . .
H7B H 0.7101 1.0394 0.1120 0.029 Uiso 1 1 calc R . .
C7A C 0.7507(3) 0.8913(3) 0.1808(2) 0.0223(9) Uani 1 1 d . . .
C7B C 0.8388(3) 0.8073(4) 0.1998(3) 0.0258(9) Uani 1 1 d . . .
C8 C 0.9141(3) 0.7548(4) 0.1565(3) 0.0351(11) Uani 1 1 d . . .
H8 H 0.9161 0.7754 0.1026 0.042 Uiso 1 1 calc R . .
C9 C 0.9858(4) 0.6717(5) 0.1951(3) 0.0420(13) Uani 1 1 d . . .
C10 C 0.9871(4) 0.6399(4) 0.2752(3) 0.0424(13) Uani 1 1 d . . .
H10 H 1.0381 0.5822 0.2991 0.051 Uiso 1 1 calc R . .
C11 C 0.9147(4) 0.6927(4) 0.3185(3) 0.0363(11) Uani 1 1 d . . .
H11 H 0.9150 0.6732 0.3728 0.044 Uiso 1 1 calc R . .
C11A C 0.8397(3) 0.7764(4) 0.2807(3) 0.0267(9) Uani 1 1 d . . .
C12A C 0.7029(3) 0.9073(4) 0.2484(2) 0.0225(9) Uani 1 1 d . . .
C12B C 0.6090(3) 0.9837(3) 0.2569(2) 0.0213(8) Uani 1 1 d . . .
C15 C 0.4544(4) 0.7529(4) -0.0740(3) 0.0309(10) Uani 1 1 d . . .
H15 H 0.5147 0.7384 -0.1020 0.037 Uiso 1 1 calc R . .
C16 C 0.3462(4) 0.7079(4) -0.1064(3) 0.0351(11) Uani 1 1 d . . .
C18 C 0.1660(5) 0.6769(5) -0.0932(3) 0.0486(13) Uani 1 1 d . . .
H18 H 0.1073 0.6832 -0.0627 0.058 Uiso 1 1 calc R . .
C19 C 0.1449(5) 0.6234(5) -0.1680(4) 0.0565(16) Uani 1 1 d . . .
H19 H 0.0737 0.5945 -0.1877 0.068 Uiso 1 1 calc R . .
C20 C 0.2287(6) 0.6137(7) -0.2121(4) 0.076(2) Uani 1 1 d . . .
H20 H 0.2168 0.5778 -0.2632 0.091 Uiso 1 1 calc R . .
C21 C 0.3315(5) 0.6568(6) -0.1814(3) 0.0559(16) Uani 1 1 d . . .
H21 H 0.3910 0.6514 -0.2113 0.067 Uiso 1 1 calc R . .
O1 O 0.2757(3) 0.8828(4) 0.0716(2) 0.0502(10) Uani 1 1 d D . .
H1A H 0.2878 0.8303 0.0385 0.060 Uiso 1 1 d RD . .
C22 C 0.1645(6) 0.9171(6) 0.0616(4) 0.0681(18) Uani 1 1 d . . .
H22A H 0.1263 0.8735 0.0996 0.102 Uiso 1 1 calc R . .
H22B H 0.1307 0.8981 0.0074 0.102 Uiso 1 1 calc R . .
H22C H 0.1591 1.0036 0.0708 0.102 Uiso 1 1 calc R . .
O2 O 0.7382(3) 0.7015(3) -0.03189(19) 0.0432(9) Uani 1 1 d . . .
H2A H 0.6964 0.7563 -0.0203 0.065 Uiso 1 1 calc R . .
C23 C 0.7300(6) 0.6003(5) 0.0189(3) 0.0575(17) Uani 1 1 d . . .
H23A H 0.7890 0.5434 0.0131 0.086 Uiso 1 1 calc R . .
H23B H 0.6589 0.5610 0.0041 0.086 Uiso 1 1 calc R . .
H23C H 0.7365 0.6273 0.0741 0.086 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 N5 C4A 129.0(4) . . ?
C6 N5 H5 115.5 . . ?
C4A N5 H5 115.5 . . ?
C11A N12 C12A 108.5(3) . . ?
C11A N12 H12 125.8 . . ?
C12A N12 H12 125.8 . . ?
C6 N13 N14 113.0(3) . . ?
C15 N14 N13 112.8(4) . . ?
C18 N17 C16 117.0(5) . . ?
C2 C1 C12B 121.7(4) . . ?
C2 C1 H1 119.1 . . ?
C12B C1 H1 119.1 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C4A 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C4A C4 H4 119.5 . . ?
C4 C4A C12B 119.4(4) . . ?
C4 C4A N5 115.8(4) . . ?
C12B C4A N5 124.6(3) . . ?
N13 C6 N5 124.2(4) . . ?
N13 C6 C7 117.1(4) . . ?
N5 C6 C7 118.8(4) . . ?
C7A C7 C6 109.7(3) . . ?
C7A C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C7A C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C12A C7A C7B 107.1(4) . . ?
C12A C7A C7 122.4(4) . . ?
C7B C7A C7 130.4(4) . . ?
C8 C7B C11A 119.8(4) . . ?
C8 C7B C7A 133.9(4) . . ?
C11A C7B C7A 106.3(4) . . ?
C9 C8 C7B 117.3(5) . . ?
C9 C8 H8 121.4 . . ?
C7B C8 H8 121.4 . . ?
C8 C9 C10 123.4(5) . . ?
C8 C9 Br1 118.3(4) . . ?
C10 C9 Br1 118.3(4) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C11A 118.5(5) . . ?
C10 C11 H11 120.8 . . ?
C11A C11 H11 120.8 . . ?
N12 C11A C11 130.0(4) . . ?
N12 C11A C7B 108.6(3) . . ?
C11 C11A C7B 121.4(4) . . ?
C7A C12A N12 109.6(4) . . ?
C7A C12A C12B 126.6(4) . . ?
N12 C12A C12B 123.9(4) . . ?
C4A C12B C1 118.3(4) . . ?
C4A C12B C12A 121.4(4) . . ?
C1 C12B C12A 120.3(4) . . ?
N14 C15 C16 121.6(4) . . ?
N14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
N17 C16 C21 122.6(5) . . ?
N17 C16 C15 118.4(4) . . ?
C21 C16 C15 119.0(5) . . ?
N17 C18 C19 123.8(6) . . ?
N17 C18 H18 118.1 . . ?
C19 C18 H18 118.1 . . ?
C20 C19 C18 118.5(6) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 119.1(6) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 119.0(6) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C22 O1 H1A 111.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O2 H2A 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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
Br1 C9 1.906(5) . ?
N5 C6 1.358(5) . ?
N5 C4A 1.410(5) . ?
N5 H5 0.8800 . ?
N12 C11A 1.370(6) . ?
N12 C12A 1.388(5) . ?
N12 H12 0.8800 . ?
N13 C6 1.309(5) . ?
N13 N14 1.399(5) . ?
N14 C15 1.274(6) . ?
N17 C18 1.329(7) . ?
N17 C16 1.352(6) . ?
C1 C2 1.374(6) . ?
C1 C12B 1.407(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C4A 1.400(6) . ?
C4 H4 0.9500 . ?
C4A C12B 1.403(6) . ?
C6 C7 1.489(6) . ?
C7 C7A 1.485(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A C12A 1.374(6) . ?
C7A C7B 1.436(6) . ?
C7B C8 1.390(6) . ?
C7B C11A 1.417(6) . ?
C8 C9 1.382(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(8) . ?
C10 C11 1.366(7) . ?
C10 H10 0.9500 . ?
C11 C11A 1.404(6) . ?
C11 H11 0.9500 . ?
C12A C12B 1.458(6) . ?
C15 C16 1.458(7) . ?
C15 H15 0.9500 . ?
C16 C21 1.386(7) . ?
C18 C19 1.398(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(9) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1 C22 1.409(8) . ?
O1 H1A 0.8400 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O2 C23 1.433(7) . ?
O2 H2A 0.8400 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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 N13 N14 C15 178.9(4) . . . . ?
C12B C1 C2 C3 0.8(7) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C2 C3 C4 C4A 0.7(7) . . . . ?
C3 C4 C4A C12B 0.7(6) . . . . ?
C3 C4 C4A N5 174.9(4) . . . . ?
C6 N5 C4A C4 146.5(4) . . . . ?
C6 N5 C4A C12B -39.7(6) . . . . ?
N14 N13 C6 N5 -1.5(5) . . . . ?
N14 N13 C6 C7 177.9(3) . . . . ?
C4A N5 C6 N13 176.8(4) . . . . ?
C4A N5 C6 C7 -2.6(6) . . . . ?
N13 C6 C7 C7A -114.8(4) . . . . ?
N5 C6 C7 C7A 64.7(5) . . . . ?
C6 C7 C7A C12A -62.2(5) . . . . ?
C6 C7 C7A C7B 115.2(5) . . . . ?
C12A C7A C7B C8 178.4(5) . . . . ?
C7 C7A C7B C8 0.7(8) . . . . ?
C12A C7A C7B C11A -0.3(4) . . . . ?
C7 C7A C7B C11A -178.0(4) . . . . ?
C11A C7B C8 C9 1.4(7) . . . . ?
C7A C7B C8 C9 -177.1(5) . . . . ?
C7B C8 C9 C10 -1.2(8) . . . . ?
C7B C8 C9 Br1 178.7(3) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
Br1 C9 C10 C11 -179.8(4) . . . . ?
C9 C10 C11 C11A 0.8(7) . . . . ?
C12A N12 C11A C11 -177.5(4) . . . . ?
C12A N12 C11A C7B 1.3(4) . . . . ?
C10 C11 C11A N12 178.1(4) . . . . ?
C10 C11 C11A C7B -0.6(6) . . . . ?
C8 C7B C11A N12 -179.5(4) . . . . ?
C7A C7B C11A N12 -0.6(4) . . . . ?
C8 C7B C11A C11 -0.6(6) . . . . ?
C7A C7B C11A C11 178.3(4) . . . . ?
C7B C7A C12A N12 1.1(5) . . . . ?
C7 C7A C12A N12 179.0(4) . . . . ?
C7B C7A C12A C12B -179.1(4) . . . . ?
C7 C7A C12A C12B -1.2(6) . . . . ?
C11A N12 C12A C7A -1.5(5) . . . . ?
C11A N12 C12A C12B 178.7(4) . . . . ?
C4 C4A C12B C1 -1.3(6) . . . . ?
N5 C4A C12B C1 -175.0(4) . . . . ?
C4 C4A C12B C12A 178.4(4) . . . . ?
N5 C4A C12B C12A 4.8(6) . . . . ?
C2 C1 C12B C4A 0.6(6) . . . . ?
C2 C1 C12B C12A -179.1(4) . . . . ?
C7A C12A C12B C4A 34.5(6) . . . . ?
N12 C12A C12B C4A -145.7(4) . . . . ?
C7A C12A C12B C1 -145.8(4) . . . . ?
N12 C12A C12B C1 34.0(6) . . . . ?
N13 N14 C15 C16 -178.6(4) . . . . ?
C18 N17 C16 C21 1.4(7) . . . . ?
C18 N17 C16 C15 -179.6(4) . . . . ?
N14 C15 C16 N17 -6.1(6) . . . . ?
N14 C15 C16 C21 172.9(5) . . . . ?
C16 N17 C18 C19 -0.9(8) . . . . ?
N17 C18 C19 C20 0.2(9) . . . . ?
C18 C19 C20 C21 0.1(10) . . . . ?
N17 C16 C21 C20 -1.2(9) . . . . ?
C15 C16 C21 C20 179.8(6) . . . . ?
C19 C20 C21 C16 0.4(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660948
