#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/81/4308106.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_4308106
loop_
_publ_author_name
'Wolfgang F. Schmid'
'Stefanie Zorbas-Seifried'
'Roland O. John'
'Vladimir B. Arion'
'Michael A. Jakupec'
'Alexander Roller'
'Markus Galanski'
'Ion Chiorescu'
'Haralabos Zorbas'
'Bernhard K. Keppler'
_publ_section_title
;
The First Ruthenium-Based Paullones: Syntheses, X-ray Diffraction
Structures, and Spectroscopic and Antiproliferative Properties in Vitro
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3645
_journal_page_last               3656
_journal_paper_doi               10.1021/ic070098j
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C22 H18 N4'
_chemical_formula_weight         338.40
_chemical_name_systematic
; 
6-(alpha-picolylamino)-7,12-dihydroindolo[3,2-d][1]benzazepine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.919(2)
_cell_length_b                   19.849(4)
_cell_length_c                   20.229(4)
_cell_measurement_temperature    120(2)
_cell_volume                     3581.2(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10302
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0526P)²+0.9684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                4190
_reflns_number_total             5462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic070098jsi20070119_060043.cif
_cod_data_source_block           WOSC063E
_cod_database_code               4308106
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
C1 C 0.35209(13) -0.12714(6) 0.36880(6) 0.0350(3) Uani 1 1 d . . .
H1 H 0.3256 -0.1667 0.3926 0.042 Uiso 1 1 calc R . .
C2 C 0.27768(14) -0.11183(6) 0.30940(6) 0.0359(3) Uani 1 1 d . . .
H2 H 0.2004 -0.1410 0.2943 0.043 Uiso 1 1 calc R . .
C3 C 0.31350(13) -0.05565(6) 0.27222(6) 0.0314(2) Uani 1 1 d . . .
H3 H 0.2646 -0.0464 0.2315 0.038 Uiso 1 1 calc R . .
C4 C 0.42461(11) -0.01302(5) 0.29706(5) 0.0258(2) Uani 1 1 d . . .
N1 N 0.47637(10) 0.04805(4) 0.27378(4) 0.02547(18) Uani 1 1 d . . .
H1A H 0.4472 0.0679 0.2371 0.031 Uiso 1 1 calc R . .
C5 C 0.58182(11) 0.07296(5) 0.31779(5) 0.02331(19) Uani 1 1 d . . .
C6 C 0.64625(11) 0.14038(5) 0.31429(5) 0.0236(2) Uani 1 1 d . . .
C7 C 0.56519(12) 0.19355(5) 0.28580(5) 0.0285(2) Uani 1 1 d . . .
H7 H 0.4722 0.1843 0.2648 0.034 Uiso 1 1 calc R . .
C8 C 0.61757(13) 0.25902(6) 0.28757(6) 0.0316(2) Uani 1 1 d . . .
H8 H 0.5612 0.2943 0.2679 0.038 Uiso 1 1 calc R . .
C9 C 0.75375(13) 0.27286(5) 0.31843(5) 0.0304(2) Uani 1 1 d . . .
H9 H 0.7890 0.3179 0.3211 0.036 Uiso 1 1 calc R . .
C10 C 0.83750(12) 0.22115(5) 0.34516(5) 0.0275(2) Uani 1 1 d . . .
H10 H 0.9313 0.2311 0.3651 0.033 Uiso 1 1 calc R . .
C11 C 0.78725(11) 0.15409(5) 0.34349(5) 0.0233(2) Uani 1 1 d . . .
N2 N 0.89104(9) 0.10507(4) 0.36377(4) 0.02438(18) Uani 1 1 d . . .
C12 C 0.85552(11) 0.05458(5) 0.40135(5) 0.0237(2) Uani 1 1 d . . .
N3 N 0.96279(10) 0.01051(5) 0.41914(4) 0.02694(19) Uani 1 1 d . . .
H3A H 0.9391(16) -0.0255(7) 0.4451(8) 0.041(4) Uiso 1 1 d . . .
C13 C 1.11884(11) 0.02408(5) 0.40333(5) 0.0275(2) Uani 1 1 d . . .
H13A H 1.1305 0.0258 0.3547 0.033 Uiso 1 1 calc R . .
H13B H 1.1815 -0.0134 0.4200 0.033 Uiso 1 1 calc R . .
C14 C 1.17473(11) 0.08960(5) 0.43276(5) 0.0267(2) Uani 1 1 d . . .
N4 N 1.13387(11) 0.10262(5) 0.49507(5) 0.0323(2) Uani 1 1 d . . .
C15 C 1.18074(16) 0.16076(6) 0.52213(6) 0.0406(3) Uani 1 1 d . . .
H15 H 1.1503 0.1708 0.5660 0.049 Uiso 1 1 calc R . .
C16 C 1.27055(16) 0.20662(6) 0.48966(7) 0.0432(3) Uani 1 1 d . . .
H16 H 1.3011 0.2472 0.5107 0.052 Uiso 1 1 calc R . .
C17 C 1.31493(15) 0.19214(6) 0.42590(7) 0.0415(3) Uani 1 1 d . . .
H17 H 1.3785 0.2221 0.4023 0.050 Uiso 1 1 calc R . .
C18 C 1.26519(13) 0.13316(6) 0.39694(6) 0.0342(2) Uani 1 1 d . . .
H18 H 1.2928 0.1225 0.3528 0.041 Uiso 1 1 calc R . .
C19 C 0.69891(11) 0.04172(5) 0.42708(5) 0.0261(2) Uani 1 1 d . . .
H19A H 0.6992 0.0024 0.4572 0.031 Uiso 1 1 calc R . .
H19B H 0.6626 0.0815 0.4519 0.031 Uiso 1 1 calc R . .
C20 C 0.59844(11) 0.02831(5) 0.36930(5) 0.0240(2) Uani 1 1 d . . .
C21 C 0.49959(11) -0.02693(5) 0.35745(5) 0.0252(2) Uani 1 1 d . . .
C22 C 0.46318(12) -0.08551(5) 0.39301(6) 0.0302(2) Uani 1 1 d . . .
H22 H 0.5140 -0.0962 0.4329 0.036 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
C22 C1 C2 120.86(11) . . ?
C22 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 122.02(11) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 117.19(11) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
N1 C4 C3 130.30(10) . . ?
N1 C4 C21 107.87(9) . . ?
C3 C4 C21 121.73(10) . . ?
C4 N1 C5 108.73(8) . . ?
C4 N1 H1A 125.6 . . ?
C5 N1 H1A 125.6 . . ?
C20 C5 N1 109.25(9) . . ?
C20 C5 C6 125.83(9) . . ?
N1 C5 C6 124.30(9) . . ?
C7 C6 C11 118.98(9) . . ?
C7 C6 C5 120.48(9) . . ?
C11 C6 C5 120.41(9) . . ?
C8 C7 C6 121.51(10) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.47(10) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.07(10) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.51(10) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
N2 C11 C10 116.05(9) . . ?
N2 C11 C6 125.05(9) . . ?
C10 C11 C6 118.39(9) . . ?
C12 N2 C11 123.06(9) . . ?
N2 C12 N3 119.04(9) . . ?
N2 C12 C19 123.90(9) . . ?
N3 C12 C19 117.06(9) . . ?
C12 N3 C13 120.11(9) . . ?
C12 N3 H3A 119.9(9) . . ?
C13 N3 H3A 119.6(9) . . ?
N3 C13 C14 112.81(9) . . ?
N3 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N4 C14 C18 122.05(10) . . ?
N4 C14 C13 116.53(10) . . ?
C18 C14 C13 121.42(10) . . ?
C14 N4 C15 117.71(10) . . ?
N4 C15 C16 123.61(12) . . ?
N4 C15 H15 118.2 . . ?
C16 C15 H15 118.2 . . ?
C15 C16 C17 118.32(12) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C18 118.73(12) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C14 119.56(11) . . ?
C17 C18 H18 120.2 . . ?
C14 C18 H18 120.2 . . ?
C20 C19 C12 108.32(8) . . ?
C20 C19 H19A 110.0 . . ?
C12 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C12 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C5 C20 C21 107.52(9) . . ?
C5 C20 C19 122.78(9) . . ?
C21 C20 C19 129.62(9) . . ?
C22 C21 C4 119.51(10) . . ?
C22 C21 C20 133.82(10) . . ?
C4 C21 C20 106.62(9) . . ?
C1 C22 C21 118.66(11) . . ?
C1 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
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
C1 C22 1.3801(17) . ?
C1 C2 1.4059(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3825(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3966(15) . ?
C3 H3 0.9500 . ?
C4 N1 1.3800(14) . ?
C4 C21 1.4200(15) . ?
N1 C5 1.3862(13) . ?
N1 H1A 0.8800 . ?
C5 C20 1.3760(14) . ?
C5 C6 1.4580(14) . ?
C6 C7 1.4032(14) . ?
C6 C11 1.4158(14) . ?
C7 C8 1.3814(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3930(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3797(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4050(15) . ?
C10 H10 0.9500 . ?
C11 N2 1.4042(13) . ?
N2 C12 1.2970(13) . ?
C12 N3 1.3454(13) . ?
C12 C19 1.5123(14) . ?
N3 C13 1.4533(14) . ?
N3 H3A 0.912(15) . ?
C13 C14 1.5147(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.3371(14) . ?
C14 C18 1.3869(16) . ?
N4 C15 1.3440(16) . ?
C15 C16 1.3789(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3796(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3822(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.4966(14) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.4273(14) . ?
C21 C22 1.4052(15) . ?
C22 H22 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
C22 C1 C2 C3 1.13(18) . . . . ?
C1 C2 C3 C4 -1.86(17) . . . . ?
C2 C3 C4 N1 -175.16(10) . . . . ?
C2 C3 C4 C21 0.85(16) . . . . ?
C3 C4 N1 C5 176.45(11) . . . . ?
C21 C4 N1 C5 0.02(11) . . . . ?
C4 N1 C5 C20 0.02(11) . . . . ?
C4 N1 C5 C6 -171.46(9) . . . . ?
C20 C5 C6 C7 -142.48(11) . . . . ?
N1 C5 C6 C7 27.59(15) . . . . ?
C20 C5 C6 C11 33.32(15) . . . . ?
N1 C5 C6 C11 -156.61(9) . . . . ?
C11 C6 C7 C8 -2.16(16) . . . . ?
C5 C6 C7 C8 173.70(10) . . . . ?
C6 C7 C8 C9 -0.16(17) . . . . ?
C7 C8 C9 C10 1.98(16) . . . . ?
C8 C9 C10 C11 -1.48(16) . . . . ?
C9 C10 C11 N2 171.37(9) . . . . ?
C9 C10 C11 C6 -0.84(15) . . . . ?
C7 C6 C11 N2 -168.84(9) . . . . ?
C5 C6 C11 N2 15.30(14) . . . . ?
C7 C6 C11 C10 2.61(14) . . . . ?
C5 C6 C11 C10 -173.25(9) . . . . ?
C10 C11 N2 C12 137.63(10) . . . . ?
C6 C11 N2 C12 -50.74(14) . . . . ?
C11 N2 C12 N3 -179.05(9) . . . . ?
C11 N2 C12 C19 0.84(15) . . . . ?
N2 C12 N3 C13 7.63(15) . . . . ?
C19 C12 N3 C13 -172.27(9) . . . . ?
C12 N3 C13 C14 58.76(13) . . . . ?
N3 C13 C14 N4 42.72(12) . . . . ?
N3 C13 C14 C18 -138.10(10) . . . . ?
C18 C14 N4 C15 1.49(16) . . . . ?
C13 C14 N4 C15 -179.34(10) . . . . ?
C14 N4 C15 C16 -1.37(19) . . . . ?
N4 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C14 -1.16(19) . . . . ?
N4 C14 C18 C17 -0.25(17) . . . . ?
C13 C14 C18 C17 -179.38(10) . . . . ?
N2 C12 C19 C20 63.69(13) . . . . ?
N3 C12 C19 C20 -116.42(10) . . . . ?
N1 C5 C20 C21 -0.06(11) . . . . ?
C6 C5 C20 C21 171.26(9) . . . . ?
N1 C5 C20 C19 -177.04(9) . . . . ?
C6 C5 C20 C19 -5.73(16) . . . . ?
C12 C19 C20 C5 -56.54(13) . . . . ?
C12 C19 C20 C21 127.19(11) . . . . ?
N1 C4 C21 C22 177.69(9) . . . . ?
C3 C4 C21 C22 0.89(15) . . . . ?
N1 C4 C21 C20 -0.06(11) . . . . ?
C3 C4 C21 C20 -176.86(9) . . . . ?
C5 C20 C21 C22 -177.22(11) . . . . ?
C19 C20 C21 C22 -0.51(19) . . . . ?
C5 C20 C21 C4 0.07(11) . . . . ?
C19 C20 C21 C4 176.78(10) . . . . ?
C2 C1 C22 C21 0.68(17) . . . . ?
C4 C21 C22 C1 -1.64(15) . . . . ?
C20 C21 C22 C1 175.37(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155832
