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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/71/4327143.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_4327143
loop_
_publ_author_name
'Iryna N. Stepanenko'
'Angela Casini'
'Fabio Edafe'
'Maria S. Novak'
'Vladimir B. Arion'
'Paul J. Dyson'
'Michael A. Jakupec'
'Bernhard K. Keppler'
_publ_section_title
;
 Conjugation of Organoruthenium(II)
 3-(1H-Benzimidazol-2-yl)pyrazolo[3,4-b]pyridines and
 Indolo[3,2-d]benzazepines to Recombinant Human Serum Albumin: a Strategy
 To Enhance Cytotoxicity in Cancer Cells
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12669
_journal_page_last               12679
_journal_paper_doi               10.1021/ic201801e
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C13 H8 Br N5, C2 H6 O S'
_chemical_formula_sum            'C15 H14 Br N5 O S'
_chemical_formula_weight         392.28
_chemical_name_systematic
; 
3-(1H-benzimidazol-2-yl)-5-bromo-1H-pyrazolo[3,4-b]pyridine
dimethyl sulfoxide 
;
_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                 94.712(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5399(4)
_cell_length_b                   10.2371(6)
_cell_length_c                   18.5633(11)
_cell_measurement_reflns_used    2875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.20
_cell_volume                     1617.39(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0846
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19277
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  0.8141
_exptl_absorpt_correction_T_min  0.4289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       stick
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                2556
_reflns_number_total             3705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic201801e_si_002_2.cif
_cod_data_source_block           irst763
_cod_database_code               4327143
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
Br1 Br 1.26088(4) 0.45826(3) 1.04603(2) 0.02482(12) Uani 1 1 d .
N1 N 1.1498(3) 1.0389(3) 0.92450(15) 0.0210(6) Uani 1 1 d .
N2 N 1.2941(3) 1.0109(3) 0.95771(15) 0.0219(6) Uani 1 1 d .
H20 H 1.3712 1.0679 0.9641 0.026 Uiso 1 1 calc R
N3 N 1.4318(3) 0.8291(2) 1.01542(15) 0.0214(6) Uani 1 1 d .
N4 N 0.8126(3) 0.8202(2) 0.89224(14) 0.0194(6) Uani 1 1 d .
N5 N 0.8312(3) 1.0346(2) 0.86750(14) 0.0199(6) Uani 1 1 d .
H5 H 0.8724 1.1132 0.8656 0.024 Uiso 1 1 calc R
C1 C 1.3050(4) 0.8851(3) 0.97974(17) 0.0193(7) Uani 1 1 d .
C2 C 1.4104(4) 0.7040(3) 1.03279(18) 0.0212(7) Uani 1 1 d .
H2 H 1.4946 0.6592 1.0587 0.025 Uiso 1 1 calc R
C3 C 1.2697(4) 0.6349(3) 1.01469(18) 0.0211(7) Uani 1 1 d .
C4 C 1.1411(4) 0.6938(3) 0.97930(18) 0.0209(7) Uani 1 1 d .
H4 H 1.0452 0.6483 0.9683 0.025 Uiso 1 1 calc R
C5 C 1.1597(4) 0.8249(3) 0.96029(17) 0.0190(7) Uani 1 1 d .
C6 C 1.0669(4) 0.9273(3) 0.92567(17) 0.0181(7) Uani 1 1 d .
C7 C 0.9039(4) 0.9248(3) 0.89587(17) 0.0177(7) Uani 1 1 d .
C8 C 0.6695(4) 0.8650(3) 0.85866(17) 0.0190(7) Uani 1 1 d .
C9 C 0.5303(4) 0.7967(3) 0.83870(17) 0.0220(8) Uani 1 1 d .
H9 H 0.5199 0.7067 0.8497 0.026 Uiso 1 1 calc R
C10 C 0.4081(4) 0.8658(3) 0.80218(19) 0.0252(8) Uani 1 1 d .
H10 H 0.3124 0.8221 0.7880 0.030 Uiso 1 1 calc R
C11 C 0.4229(4) 0.9974(3) 0.78602(19) 0.0262(8) Uani 1 1 d .
H11 H 0.3369 1.0407 0.7606 0.031 Uiso 1 1 calc R
C12 C 0.5578(4) 1.0681(3) 0.80548(18) 0.0243(8) Uani 1 1 d .
H12 H 0.5665 1.1583 0.7945 0.029 Uiso 1 1 calc R
C13 C 0.6809(4) 0.9985(3) 0.84241(17) 0.0196(7) Uani 1 1 d .
S1 S 0.03807(10) 0.37818(8) 0.85448(5) 0.0246(2) Uani 1 1 d .
O1 O -0.0925(3) 0.2886(2) 0.82658(13) 0.0310(6) Uani 1 1 d .
C14 C 0.2097(4) 0.3192(4) 0.8161(2) 0.0357(10) Uani 1 1 d .
H14A H 0.2432 0.2368 0.8394 0.054 Uiso 1 1 calc R
H14B H 0.2942 0.3838 0.8236 0.054 Uiso 1 1 calc R
H14C H 0.1859 0.3046 0.7641 0.054 Uiso 1 1 calc R
C15 C 0.0131(4) 0.5258(3) 0.8021(2) 0.0313(9) Uani 1 1 d .
H15A H -0.0074 0.5036 0.7508 0.047 Uiso 1 1 calc R
H15B H 0.1090 0.5786 0.8088 0.047 Uiso 1 1 calc R
H15C H -0.0757 0.5757 0.8180 0.047 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'
S S 0.1246 0.1234 '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
C6 N1 N2 105.7(3)
C1 N2 N1 112.0(3)
C1 N2 H20 124.0
N1 N2 H20 124.0
C2 N3 C1 113.9(3)
C7 N4 C8 104.2(3)
C7 N5 C13 106.9(3)
C7 N5 H5 126.6
C13 N5 H5 126.6
N3 C1 N2 125.8(3)
N3 C1 C5 126.5(3)
N2 C1 C5 107.6(3)
N3 C2 C3 123.6(3)
N3 C2 H2 118.2
C3 C2 H2 118.2
C4 C3 C2 121.7(3)
C4 C3 Br1 120.9(2)
C2 C3 Br1 117.2(2)
C3 C4 C5 116.1(3)
C3 C4 H4 122.0
C5 C4 H4 122.0
C4 C5 C1 118.1(3)
C4 C5 C6 138.1(3)
C1 C5 C6 103.8(3)
N1 C6 C5 110.8(3)
N1 C6 C7 119.8(3)
C5 C6 C7 129.3(3)
N4 C7 N5 113.5(3)
N4 C7 C6 125.1(3)
N5 C7 C6 121.4(3)
C9 C8 N4 130.0(3)
C9 C8 C13 120.0(3)
N4 C8 C13 109.9(3)
C10 C9 C8 117.5(3)
C10 C9 H9 121.3
C8 C9 H9 121.3
C11 C10 C9 121.4(3)
C11 C10 H10 119.3
C9 C10 H10 119.3
C12 C11 C10 122.7(3)
C12 C11 H11 118.7
C10 C11 H11 118.6
C11 C12 C13 115.9(3)
C11 C12 H12 122.1
C13 C12 H12 122.1
N5 C13 C12 131.9(3)
N5 C13 C8 105.5(3)
C12 C13 C8 122.5(3)
O1 S1 C14 105.43(16)
O1 S1 C15 105.94(16)
C14 S1 C15 97.62(17)
S1 C14 H14A 109.5
S1 C14 H14B 109.5
H14A C14 H14B 109.5
S1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
S1 C15 H15A 109.5
S1 C15 H15B 109.5
H15A C15 H15B 109.5
S1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.903(3)
N1 C6 1.345(4)
N1 N2 1.363(4)
N2 C1 1.352(4)
N2 H20 0.8800
N3 C2 1.337(4)
N3 C1 1.349(4)
N4 C7 1.323(4)
N4 C8 1.403(4)
N5 C7 1.369(4)
N5 C13 1.379(4)
N5 H5 0.8800
C1 C5 1.406(4)
C2 C3 1.411(4)
C2 H2 0.9500
C3 C4 1.372(4)
C4 C5 1.400(4)
C4 H4 0.9500
C5 C6 1.434(4)
C6 C7 1.455(4)
C8 C9 1.402(4)
C8 C13 1.404(4)
C9 C10 1.390(4)
C9 H9 0.9500
C10 C11 1.388(5)
C10 H10 0.9500
C11 C12 1.383(5)
C11 H11 0.9500
C12 C13 1.402(4)
C12 H12 0.9500
S1 O1 1.503(2)
S1 C14 1.787(4)
S1 C15 1.801(3)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 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
C6 N1 N2 C1 0.1(4)
C2 N3 C1 N2 178.2(3)
C2 N3 C1 C5 -0.1(5)
N1 N2 C1 N3 -178.6(3)
N1 N2 C1 C5 0.0(4)
C1 N3 C2 C3 1.1(5)
N3 C2 C3 C4 -2.1(5)
N3 C2 C3 Br1 -178.7(3)
C2 C3 C4 C5 2.0(5)
Br1 C3 C4 C5 178.5(2)
C3 C4 C5 C1 -1.1(5)
C3 C4 C5 C6 -178.7(4)
N3 C1 C5 C4 0.2(5)
N2 C1 C5 C4 -178.4(3)
N3 C1 C5 C6 178.5(3)
N2 C1 C5 C6 0.0(4)
N2 N1 C6 C5 -0.1(4)
N2 N1 C6 C7 178.3(3)
C4 C5 C6 N1 177.9(4)
C1 C5 C6 N1 0.1(4)
C4 C5 C6 C7 -0.2(7)
C1 C5 C6 C7 -178.1(3)
C8 N4 C7 N5 0.3(4)
C8 N4 C7 C6 -179.0(3)
C13 N5 C7 N4 -0.9(4)
C13 N5 C7 C6 178.4(3)
N1 C6 C7 N4 178.0(3)
C5 C6 C7 N4 -4.0(6)
N1 C6 C7 N5 -1.2(5)
C5 C6 C7 N5 176.9(3)
C7 N4 C8 C9 177.9(3)
C7 N4 C8 C13 0.5(3)
N4 C8 C9 C10 -176.5(3)
C13 C8 C9 C10 0.7(5)
C8 C9 C10 C11 0.0(5)
C9 C10 C11 C12 -0.6(5)
C10 C11 C12 C13 0.5(5)
C7 N5 C13 C12 -176.5(3)
C7 N5 C13 C8 1.1(3)
C11 C12 C13 N5 177.5(3)
C11 C12 C13 C8 0.3(5)
C9 C8 C13 N5 -178.7(3)
N4 C8 C13 N5 -1.0(4)
C9 C8 C13 C12 -0.9(5)
N4 C8 C13 C12 176.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661187
