#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:55:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179218 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/44/4314476.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_4314476
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         'C20 H21 Br Cl2 Cu N4'
_chemical_formula_sum            'C20 H21 Br Cl2 Cu N4'
_chemical_formula_weight         531.76
_chemical_name_systematic
; 
9-Bromo-6-N-(2-N',N'-dimethylamino)-7,12-dihydroindolo[3,2-d][1]
benzazepino-dichlorido-copper(II)  
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.613(4)
_cell_angle_beta                 93.568(4)
_cell_angle_gamma                115.547(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1511(5)
_cell_length_b                   10.8098(6)
_cell_length_c                   11.7944(9)
_cell_measurement_reflns_used    922
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.35
_cell_volume                     1025.79(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            40020
_diffrn_reflns_theta_full        30.16
_diffrn_reflns_theta_max         30.16
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    3.287
_exptl_absorpt_correction_T_max  0.9078
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0337
_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)+(0.0317P)²+0.8983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                4425
_reflns_number_total             6020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902042a_si_002_1.cif
_cod_data_source_block           MIPR024
_cod_original_cell_volume        1025.78(11)
_cod_database_code               4314476
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
Br1 Br 0.71562(3) 0.96997(3) 0.45316(2) 0.02114(8) Uani 1 1 d . . .
Cu1 Cu 0.13097(3) 0.35900(4) 0.21795(3) 0.01438(8) Uani 1 1 d . . .
Cl1 Cl -0.01998(7) 0.30733(7) 0.03573(6) 0.01729(13) Uani 1 1 d . . .
Cl2 Cl 0.20737(8) 0.60924(8) 0.33275(6) 0.02485(15) Uani 1 1 d . . .
N1 N 0.7174(2) 0.4017(2) 0.0709(2) 0.0155(4) Uani 1 1 d . . .
H1 H 0.7901 0.3806 0.0512 0.019 Uiso 1 1 calc R . .
N2 N 0.2714(2) 0.0485(2) -0.00260(19) 0.0145(4) Uani 1 1 d . . .
H200 H 0.2286 -0.0246 0.0202 0.017 Uiso 1 1 calc R . .
N3 N 0.1713(2) 0.1847(2) 0.13715(19) 0.0139(4) Uani 1 1 d . . .
N4 N 0.1458(2) 0.3159(2) 0.36969(19) 0.0162(4) Uani 1 1 d . . .
C1 C 0.7196(3) 0.7903(3) 0.3334(2) 0.0160(5) Uani 1 1 d . . .
C2 C 0.8619(3) 0.8009(3) 0.3327(2) 0.0171(5) Uani 1 1 d . . .
H2 H 0.9514 0.8952 0.3915 0.021 Uiso 1 1 calc R . .
C3 C 0.8741(3) 0.6766(3) 0.2481(2) 0.0172(5) Uani 1 1 d . . .
H3 H 0.9703 0.6832 0.2467 0.021 Uiso 1 1 calc R . .
C4 C 0.7380(3) 0.5401(3) 0.1642(2) 0.0147(5) Uani 1 1 d . . .
C5 C 0.5627(3) 0.3008(3) 0.0131(2) 0.0147(5) Uani 1 1 d . . .
C6 C 0.4968(3) 0.1397(3) -0.0863(2) 0.0147(5) Uani 1 1 d . . .
C7 C 0.5721(3) 0.0973(3) -0.1784(2) 0.0177(5) Uani 1 1 d . . .
H7 H 0.6648 0.1756 -0.1772 0.021 Uiso 1 1 calc R . .
C8 C 0.5138(3) -0.0557(3) -0.2704(2) 0.0214(6) Uani 1 1 d . . .
H8 H 0.5646 -0.0820 -0.3333 0.026 Uiso 1 1 calc R . .
C9 C 0.3805(3) -0.1711(3) -0.2708(2) 0.0220(6) Uani 1 1 d . . .
H9 H 0.3423 -0.2771 -0.3318 0.026 Uiso 1 1 calc R . .
C10 C 0.3031(3) -0.1323(3) -0.1825(2) 0.0183(5) Uani 1 1 d . . .
H10 H 0.2116 -0.2121 -0.1839 0.022 Uiso 1 1 calc R . .
C11 C 0.3577(3) 0.0228(3) -0.0913(2) 0.0141(5) Uani 1 1 d . . .
C12 C 0.2462(3) 0.1704(3) 0.0515(2) 0.0130(5) Uani 1 1 d . . .
C13 C 0.1324(3) 0.0814(3) 0.1958(2) 0.0165(5) Uani 1 1 d . . .
H13A H 0.2239 0.0798 0.2276 0.020 Uiso 1 1 calc R . .
H13B H 0.0544 -0.0261 0.1311 0.020 Uiso 1 1 calc R . .
C14 C 0.0712(3) 0.1434(3) 0.3076(2) 0.0185(5) Uani 1 1 d . . .
H14A H -0.0401 0.0975 0.2752 0.022 Uiso 1 1 calc R . .
H14B H 0.0898 0.1118 0.3722 0.022 Uiso 1 1 calc R . .
C15 C 0.3083(3) 0.3898(3) 0.4381(3) 0.0246(6) Uani 1 1 d . . .
H15A H 0.3609 0.3540 0.3768 0.037 Uiso 1 1 calc R . .
H15B H 0.3163 0.3609 0.5061 0.037 Uiso 1 1 calc R . .
H15C H 0.3552 0.5032 0.4768 0.037 Uiso 1 1 calc R . .
C16 C 0.0661(3) 0.3693(3) 0.4619(2) 0.0228(6) Uani 1 1 d . . .
H16A H -0.0415 0.3200 0.4165 0.034 Uiso 1 1 calc R . .
H16B H 0.1127 0.4828 0.5004 0.034 Uiso 1 1 calc R . .
H16C H 0.0743 0.3407 0.5300 0.034 Uiso 1 1 calc R . .
C17 C 0.3147(3) 0.2961(3) 0.0139(2) 0.0139(5) Uani 1 1 d . . .
H17A H 0.2788 0.3716 0.0507 0.017 Uiso 1 1 calc R . .
H17B H 0.2847 0.2509 -0.0813 0.017 Uiso 1 1 calc R . .
C18 C 0.4842(3) 0.3755(3) 0.0654(2) 0.0129(5) Uani 1 1 d . . .
C19 C 0.5932(3) 0.5289(3) 0.1645(2) 0.0128(5) Uani 1 1 d . . .
C20 C 0.5837(3) 0.6574(3) 0.2511(2) 0.0138(5) Uani 1 1 d . . .
H20 H 0.4885 0.6532 0.2532 0.017 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
N3 Cu1 N4 81.77(9) . . ?
N3 Cu1 Cl2 151.99(6) . . ?
N4 Cu1 Cl2 96.72(6) . . ?
N3 Cu1 Cl1 96.96(6) . . ?
N4 Cu1 Cl1 147.45(6) . . ?
Cl2 Cu1 Cl1 98.83(3) . . ?
C4 N1 C5 108.2(2) . . ?
C4 N1 H1 125.9 . . ?
C5 N1 H1 125.9 . . ?
C12 N2 C11 128.9(2) . . ?
C12 N2 H200 115.6 . . ?
C11 N2 H200 115.6 . . ?
C12 N3 C13 119.9(2) . . ?
C12 N3 Cu1 124.57(18) . . ?
C13 N3 Cu1 114.79(15) . . ?
C16 N4 C15 109.6(2) . . ?
C16 N4 C14 109.4(2) . . ?
C15 N4 C14 111.1(2) . . ?
C16 N4 Cu1 114.04(17) . . ?
C15 N4 Cu1 109.14(17) . . ?
C14 N4 Cu1 103.47(15) . . ?
C20 C1 C2 123.1(2) . . ?
C20 C1 Br1 119.22(19) . . ?
C2 C1 Br1 117.65(18) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
N1 C4 C3 129.1(2) . . ?
N1 C4 C19 108.8(2) . . ?
C3 C4 C19 122.1(2) . . ?
C18 C5 N1 109.6(2) . . ?
C18 C5 C6 126.4(2) . . ?
N1 C5 C6 123.9(2) . . ?
C7 C6 C11 118.7(2) . . ?
C7 C6 C5 120.5(2) . . ?
C11 C6 C5 120.8(2) . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 119.2(2) . . ?
C10 C11 N2 116.0(2) . . ?
C6 C11 N2 124.6(2) . . ?
N3 C12 N2 123.1(2) . . ?
N3 C12 C17 119.4(2) . . ?
N2 C12 C17 117.4(2) . . ?
N3 C13 C14 107.9(2) . . ?
N3 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
N3 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N4 C14 C13 110.9(2) . . ?
N4 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 C18 107.42(19) . . ?
C12 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
C12 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C5 C18 C19 107.5(2) . . ?
C5 C18 C17 120.7(2) . . ?
C19 C18 C17 131.7(2) . . ?
C20 C19 C4 119.8(2) . . ?
C20 C19 C18 134.4(2) . . ?
C4 C19 C18 105.8(2) . . ?
C1 C20 C19 116.9(2) . . ?
C1 C20 H20 121.6 . . ?
C19 C20 H20 121.6 . . ?
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 C1 1.909(3) . ?
Cu1 N3 1.975(2) . ?
Cu1 N4 2.034(2) . ?
Cu1 Cl2 2.2085(7) . ?
Cu1 Cl1 2.2736(7) . ?
N1 C4 1.369(3) . ?
N1 C5 1.384(3) . ?
N1 H1 0.8800 . ?
N2 C12 1.359(3) . ?
N2 C11 1.424(3) . ?
N2 H200 0.8800 . ?
N3 C12 1.302(3) . ?
N3 C13 1.467(3) . ?
N4 C16 1.477(3) . ?
N4 C15 1.480(3) . ?
N4 C14 1.485(3) . ?
C1 C20 1.384(3) . ?
C1 C2 1.400(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(3) . ?
C3 H3 0.9500 . ?
C4 C19 1.423(3) . ?
C5 C18 1.373(3) . ?
C5 C6 1.454(3) . ?
C6 C7 1.408(3) . ?
C6 C11 1.409(4) . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(3) . ?
C10 H10 0.9500 . ?
C12 C17 1.494(3) . ?
C13 C14 1.526(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.498(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.429(3) . ?
C19 C20 1.405(3) . ?
C20 H20 0.9500 . ?
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
N4 Cu1 N3 C12 -147.8(2) . . . . ?
Cl2 Cu1 N3 C12 -59.0(3) . . . . ?
Cl1 Cu1 N3 C12 65.00(19) . . . . ?
N4 Cu1 N3 C13 22.40(16) . . . . ?
Cl2 Cu1 N3 C13 111.25(18) . . . . ?
Cl1 Cu1 N3 C13 -124.78(15) . . . . ?
N3 Cu1 N4 C16 -156.63(19) . . . . ?
Cl2 Cu1 N4 C16 51.58(18) . . . . ?
Cl1 Cu1 N4 C16 -66.6(2) . . . . ?
N3 Cu1 N4 C15 80.44(17) . . . . ?
Cl2 Cu1 N4 C15 -71.35(17) . . . . ?
Cl1 Cu1 N4 C15 170.50(13) . . . . ?
N3 Cu1 N4 C14 -37.94(15) . . . . ?
Cl2 Cu1 N4 C14 170.27(14) . . . . ?
Cl1 Cu1 N4 C14 52.1(2) . . . . ?
C20 C1 C2 C3 0.1(4) . . . . ?
Br1 C1 C2 C3 -179.33(19) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C5 N1 C4 C3 179.8(3) . . . . ?
C5 N1 C4 C19 -1.2(3) . . . . ?
C2 C3 C4 N1 179.4(2) . . . . ?
C2 C3 C4 C19 0.5(4) . . . . ?
C4 N1 C5 C18 2.2(3) . . . . ?
C4 N1 C5 C6 -176.8(2) . . . . ?
C18 C5 C6 C7 145.8(3) . . . . ?
N1 C5 C6 C7 -35.3(4) . . . . ?
C18 C5 C6 C11 -35.0(4) . . . . ?
N1 C5 C6 C11 143.9(2) . . . . ?
C11 C6 C7 C8 -1.5(4) . . . . ?
C5 C6 C7 C8 177.8(2) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C7 C8 C9 C10 2.6(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C6 -2.7(4) . . . . ?
C9 C10 C11 N2 -178.0(2) . . . . ?
C7 C6 C11 C10 3.6(3) . . . . ?
C5 C6 C11 C10 -175.6(2) . . . . ?
C7 C6 C11 N2 178.5(2) . . . . ?
C5 C6 C11 N2 -0.7(4) . . . . ?
C12 N2 C11 C10 -145.8(2) . . . . ?
C12 N2 C11 C6 39.1(4) . . . . ?
C13 N3 C12 N2 10.5(3) . . . . ?
Cu1 N3 C12 N2 -179.73(16) . . . . ?
C13 N3 C12 C17 -166.7(2) . . . . ?
Cu1 N3 C12 C17 3.1(3) . . . . ?
C11 N2 C12 N3 -176.2(2) . . . . ?
C11 N2 C12 C17 1.0(3) . . . . ?
C12 N3 C13 C14 170.1(2) . . . . ?
Cu1 N3 C13 C14 -0.6(2) . . . . ?
C16 N4 C14 C13 170.4(2) . . . . ?
C15 N4 C14 C13 -68.5(3) . . . . ?
Cu1 N4 C14 C13 48.5(2) . . . . ?
N3 C13 C14 N4 -32.4(3) . . . . ?
N3 C12 C17 C18 110.7(2) . . . . ?
N2 C12 C17 C18 -66.6(3) . . . . ?
N1 C5 C18 C19 -2.4(3) . . . . ?
C6 C5 C18 C19 176.6(2) . . . . ?
N1 C5 C18 C17 175.9(2) . . . . ?
C6 C5 C18 C17 -5.2(4) . . . . ?
C12 C17 C18 C5 70.3(3) . . . . ?
C12 C17 C18 C19 -112.0(3) . . . . ?
N1 C4 C19 C20 -179.2(2) . . . . ?
C3 C4 C19 C20 -0.1(4) . . . . ?
N1 C4 C19 C18 -0.3(3) . . . . ?
C3 C4 C19 C18 178.8(2) . . . . ?
C5 C18 C19 C20 -179.7(3) . . . . ?
C17 C18 C19 C20 2.4(5) . . . . ?
C5 C18 C19 C4 1.6(3) . . . . ?
C17 C18 C19 C4 -176.4(2) . . . . ?
C2 C1 C20 C19 0.3(4) . . . . ?
Br1 C1 C20 C19 179.68(18) . . . . ?
C4 C19 C20 C1 -0.2(3) . . . . ?
C18 C19 C20 C1 -178.8(3) . . . . ?
