#------------------------------------------------------------------------------
#$Date: 2016-09-10 02:35:32 +0300 (Sat, 10 Sep 2016) $
#$Revision: 186420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/91/7039196.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_7039196
loop_
_publ_author_name
'Kubanik, Mario'
'Kandioller, Wolfgang'
'Kim, Kunwoo'
'Anderson, Robert F.'
'Klapproth, Erik'
'Jakupec, Michael A.'
'Roller, Alexander'
'Söhnel, Tilo'
'Keppler, Bernhard K.'
'Hartinger, Christian G.'
_publ_section_title
;
 Towards targeting anticancer drugs: ruthenium(ii)-arene complexes with
 biologically active naphthoquinone-derived ligand systems.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13091
_journal_page_last               13103
_journal_paper_doi               10.1039/c6dt01110a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.25
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-17 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.488(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8478(4)
_cell_length_b                   6.9261(2)
_cell_length_c                   13.7030(4)
_cell_measurement_reflns_used    4208
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.212
_cell_measurement_theta_min      3.112
_cell_volume                     1112.14(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11807
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.006
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0531
_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)+(0.0493P)²+0.2872P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1492
_reflns_number_total             2184
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01110a2.cif
_cod_data_source_block           maku238
_cod_depositor_comments
'Adding full bibliography for 7039193--7039196.cif.'
_cod_database_code               7039196
_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   0.963
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
C1 C 0.48286(17) 0.2586(3) 0.48892(14) 0.0193(5) Uani 1 1 d D . . . .
C1' C 0.80362(17) 0.1189(3) 0.54348(15) 0.0251(5) Uani 1 1 d . . . . .
H1'1 H 0.8075 0.0831 0.4741 0.030 Uiso 1 1 calc R U . . .
H1'2 H 0.8309 0.0075 0.5857 0.030 Uiso 1 1 calc R U . . .
C2 C 0.60251(17) 0.2151(3) 0.47844(14) 0.0200(5) Uani 1 1 d D . . . .
C2' C 0.88151(17) 0.2923(3) 0.57197(16) 0.0275(5) Uani 1 1 d . . . . .
H2'1 H 0.8582 0.3996 0.5256 0.033 Uiso 1 1 calc R U . . .
H2'2 H 0.8713 0.3359 0.6389 0.033 Uiso 1 1 calc R U . . .
C3' C 1.00734(18) 0.2480(3) 0.57075(17) 0.0345(6) Uani 1 1 d . . . . .
H3'1 H 1.0319 0.1452 0.6183 0.052 Uiso 1 1 calc R U . . .
H3'2 H 1.0527 0.3644 0.5886 0.052 Uiso 1 1 calc R U . . .
H3'3 H 1.0183 0.2060 0.5045 0.052 Uiso 1 1 calc R U . . .
C3 C 0.68198(17) 0.1622(3) 0.55478(14) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.65065(17) 0.1536(3) 0.65298(14) 0.0217(5) Uani 1 1 d . . . . .
C5 C 0.50428(19) 0.1964(3) 0.76360(14) 0.0258(5) Uani 1 1 d . . . . .
H5 H 0.5611 0.1641 0.8175 0.031 Uiso 1 1 calc R U . . .
C5A C 0.53257(17) 0.2020(3) 0.66820(14) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.39493(19) 0.2373(3) 0.78058(16) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.3764 0.2323 0.8457 0.036 Uiso 1 1 calc R U . . .
C7 C 0.31247(19) 0.2856(3) 0.70202(15) 0.0292(5) Uani 1 1 d . . . . .
H7 H 0.2371 0.3140 0.7136 0.035 Uiso 1 1 calc R U . . .
C8 C 0.33821(18) 0.2931(3) 0.60681(15) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.2805 0.3264 0.5537 0.029 Uiso 1 1 calc R U . . .
C8A C 0.44894(17) 0.2520(3) 0.58824(14) 0.0201(5) Uani 1 1 d . . . . .
N1 N 0.4241(4) 0.2941(13) 0.4038(2) 0.0244(10) Uani 0.740(2) 1 d D . P A 1
O1 O 0.31215(17) 0.3334(3) 0.40412(13) 0.0271(5) Uani 0.740(2) 1 d D . P A 1
H1 H 0.2805 0.3550 0.3462 0.041 Uiso 0.740(2) 1 calc R U P A 1
O2 O 0.6298(12) 0.2354(17) 0.3863(5) 0.0250(15) Uani 0.740(2) 1 d D . P A 1
H2 H 0.5708 0.2626 0.3467 0.038 Uiso 0.740(2) 1 calc R U P A 1
N1A N 0.4026(14) 0.309(4) 0.4187(7) 0.0244(10) Uani 0.260(2) 1 d D . P A 2
O1A O 0.4240(5) 0.3198(8) 0.3241(4) 0.0271(5) Uani 0.260(2) 1 d D . P A 2
H1A H 0.4838 0.2580 0.3188 0.041 Uiso 0.260(2) 1 calc R U P A 2
O2A O 0.637(4) 0.204(6) 0.3882(15) 0.0250(15) Uani 0.260(2) 1 d D . P A 2
H2A H 0.7027 0.2510 0.3913 0.038 Uiso 0.260(2) 1 calc R U P A 2
O3 O 0.72203(12) 0.1033(2) 0.72400(10) 0.0322(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
N1 C1 C8A 130.9(3)
N1A C1 C8A 115.0(7)
N1 C1 C2 110.4(3)
N1A C1 C2 126.3(7)
C8A C1 C2 118.64(17)
C3 C1' C2' 111.67(16)
C3 C1' H1'1 109.3
C2' C1' H1'1 109.3
C3 C1' H1'2 109.3
C2' C1' H1'2 109.3
H1'1 C1' H1'2 107.9
C3 C2 O2 121.0(6)
C3 C2 O2A 115.0(18)
C3 C2 C1 123.33(18)
O2 C2 C1 115.7(6)
O2A C2 C1 121.3(18)
C3' C2' C1' 113.18(17)
C3' C2' H2'1 108.9
C1' C2' H2'1 108.9
C3' C2' H2'2 108.9
C1' C2' H2'2 108.9
H2'1 C2' H2'2 107.8
C2' C3' H3'1 109.5
C2' C3' H3'2 109.5
H3'1 C3' H3'2 109.5
C2' C3' H3'3 109.5
H3'1 C3' H3'3 109.5
H3'2 C3' H3'3 109.5
C2 C3 C4 119.05(18)
C2 C3 C1' 122.96(18)
C4 C3 C1' 117.95(17)
O3 C4 C3 120.09(19)
O3 C4 C5A 120.05(18)
C3 C4 C5A 119.84(17)
C6 C5 C5A 120.89(19)
C6 C5 H5 119.6
C5A C5 H5 119.6
C5 C5A C8A 119.76(19)
C5 C5A C4 119.15(17)
C8A C5A C4 121.09(17)
C5 C6 C7 119.43(19)
C5 C6 H6 120.3
C7 C6 H6 120.3
C6 C7 C8 120.9(2)
C6 C7 H7 119.5
C8 C7 H7 119.5
C7 C8 C8A 120.38(19)
C7 C8 H8 119.8
C8A C8 H8 119.8
C8 C8A C5A 118.60(18)
C8 C8A C1 123.40(18)
C5A C8A C1 117.99(18)
C1 N1 O1 115.6(3)
N1 O1 H1 109.5
C2 O2 H2 109.5
C1 N1A O1A 120.1(12)
N1A O1A H1A 109.5
C2 O2A H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.291(3)
C1 N1A 1.298(8)
C1 C8A 1.476(3)
C1 C2 1.477(3)
C1' C3 1.502(3)
C1' C2' 1.529(3)
C1' H1'1 0.9900
C1' H1'2 0.9900
C2 C3 1.351(3)
C2 O2 1.356(4)
C2 O2A 1.359(8)
C2' C3' 1.524(3)
C2' H2'1 0.9900
C2' H2'2 0.9900
C3' H3'1 0.9800
C3' H3'2 0.9800
C3' H3'3 0.9800
C3 C4 1.449(3)
C4 O3 1.241(2)
C4 C5A 1.483(3)
C5 C6 1.379(3)
C5 C5A 1.397(3)
C5 H5 0.9500
C5A C8A 1.408(3)
C6 C7 1.384(3)
C6 H6 0.9500
C7 C8 1.384(3)
C7 H7 0.9500
C8 C8A 1.402(3)
C8 H8 0.9500
N1 O1 1.354(5)
O1 H1 0.8400
O2 H2 0.8400
N1A O1A 1.360(11)
O1A H1A 0.8400
O2A H2A 0.8400
