#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:53:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179429 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/26/4332690.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4332690
loop_
_publ_author_name
'Halder, Sarmistha'
'Acharyya, Rama'
'Peng, Shie-Ming'
'Lee, Gene-Hsiang'
'Drew, Michael G. B.'
'Bhattacharya, Samaresh'
_publ_section_title
;
 Synthesis, Structure, and Electrochemical Properties of a Family of
 2-(Arylazo)phenolate Complexes of Ruthenium with Unusual C−C
 Coupling and NN Cleavage
;
_journal_issue                   24
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9654
_journal_page_last               9663
_journal_paper_doi               10.1021/ic060689u
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C37 H37 N5 O3 Ru'
_chemical_formula_weight         700.79
_chemical_name_systematic
; 
 ? 
;
_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                 106.3570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6497(2)
_cell_length_b                   19.4497(5)
_cell_length_c                   16.6027(5)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.99
_cell_volume                     3299.78(15)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20549
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.964
_refine_diff_density_min         -1.978
_refine_diff_density_rms         0.192
_refine_ls_extinction_coef       0.0101(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0898
_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)+(0.0872P)²+27.4641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2318
_reflns_number_gt                4683
_reflns_number_total             5812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic060689usup4.cif
_cod_data_source_block           ic8896
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3299.78(14)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4332690
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
Ru Ru 0.62672(6) 0.20371(3) 0.04859(4) 0.0378(3) Uani 1 1 d .
O1 O 0.7824(5) 0.2667(3) 0.0794(4) 0.0429(13) Uani 1 1 d .
O2 O 0.6288(6) 0.2155(3) -0.0714(4) 0.0482(15) Uani 1 1 d .
O3 O 0.4711(6) 0.1364(3) 0.0196(4) 0.0520(16) Uani 1 1 d .
N1 N 0.5008(7) 0.2850(4) 0.0248(4) 0.0464(17) Uani 1 1 d .
N2 N 0.5229(8) 0.3461(4) 0.0156(4) 0.0462(17) Uani 1 1 d .
N3 N 0.7656(7) 0.1289(4) 0.0403(5) 0.0472(17) Uani 1 1 d .
N4 N 0.8348(7) 0.0884(4) 0.0875(5) 0.057(2) Uani 1 1 d .
N5 N 0.6093(7) 0.1855(4) 0.1599(5) 0.052(2) Uani 1 1 d .
H5D H 0.6673 0.1986 0.2064 0.062 Uiso 1 1 calc R
C1 C 0.7739(7) 0.3324(4) 0.0648(4) 0.0334(17) Uani 1 1 d .
C2 C 0.8915(8) 0.3720(4) 0.0841(5) 0.0382(18) Uani 1 1 d .
H2A H 0.9725 0.3495 0.1082 0.046 Uiso 1 1 calc R
C3 C 0.8918(7) 0.4405(4) 0.0694(5) 0.0370(18) Uani 1 1 d .
H3A H 0.9727 0.4646 0.0833 0.044 Uiso 1 1 calc R
C4 C 0.7749(8) 0.4768(4) 0.0341(5) 0.0377(18) Uani 1 1 d .
C5 C 0.7778(10) 0.5520(5) 0.0131(7) 0.061(3) Uani 1 1 d .
H5A H 0.6882 0.5687 -0.0106 0.092 Uiso 1 1 calc R
H5B H 0.8275 0.5584 -0.0279 0.092 Uiso 1 1 calc R
H5C H 0.8198 0.5779 0.0643 0.092 Uiso 1 1 calc R
C6 C 0.6608(7) 0.4394(4) 0.0163(5) 0.0365(17) Uani 1 1 d .
H6A H 0.5807 0.4628 -0.0077 0.044 Uiso 1 1 calc R
C7 C 0.6562(7) 0.3689(4) 0.0314(5) 0.0360(18) Uani 1 1 d .
C8 C 0.3622(7) 0.2767(4) 0.0208(5) 0.0355(17) Uani 1 1 d .
C9 C 0.3245(7) 0.2905(4) 0.0930(5) 0.0343(17) Uani 1 1 d .
C10 C 0.1985(8) 0.2724(5) 0.0937(6) 0.048(2) Uani 1 1 d .
H10A H 0.1718 0.2792 0.1431 0.057 Uiso 1 1 calc R
C11 C 0.1131(9) 0.2450(6) 0.0242(6) 0.057(3) Uani 1 1 d .
H11A H 0.0267 0.2337 0.0252 0.069 Uiso 1 1 calc R
C12 C 0.1509(8) 0.2335(5) -0.0484(6) 0.048(2) Uani 1 1 d .
H12A H 0.0895 0.2151 -0.0967 0.058 Uiso 1 1 calc R
C13 C 0.2768(7) 0.2483(4) -0.0512(5) 0.0322(16) Uani 1 1 d .
C14 C 0.4150(8) 0.3241(5) 0.1690(5) 0.047(2) Uani 1 1 d .
H14A H 0.4995 0.3333 0.1585 0.071 Uiso 1 1 calc R
H14B H 0.4278 0.2935 0.2175 0.071 Uiso 1 1 calc R
H14C H 0.3765 0.3675 0.1804 0.071 Uiso 1 1 calc R
C15 C 0.3150(8) 0.2356(5) -0.1297(5) 0.047(2) Uani 1 1 d .
H15A H 0.2407 0.2159 -0.1724 0.071 Uiso 1 1 calc R
H15B H 0.3888 0.2035 -0.1179 0.071 Uiso 1 1 calc R
H15C H 0.3407 0.2791 -0.1503 0.071 Uiso 1 1 calc R
C16 C 0.7175(8) 0.1796(4) -0.0934(5) 0.0397(18) Uani 1 1 d .
C17 C 0.7384(8) 0.1880(5) -0.1725(5) 0.046(2) Uani 1 1 d .
H17A H 0.6878 0.2206 -0.2107 0.055 Uiso 1 1 calc R
C18 C 0.8294(8) 0.1505(5) -0.1949(5) 0.048(2) Uani 1 1 d .
H18A H 0.8403 0.1571 -0.2492 0.057 Uiso 1 1 calc R
C19 C 0.9086(8) 0.1020(4) -0.1415(5) 0.044(2) Uani 1 1 d .
C20 C 1.0116(11) 0.0618(6) -0.1681(8) 0.072(3) Uani 1 1 d .
H20A H 1.0565 0.0306 -0.1228 0.108 Uiso 1 1 calc R
H20B H 1.0752 0.0936 -0.1802 0.108 Uiso 1 1 calc R
H20C H 0.9699 0.0350 -0.2185 0.108 Uiso 1 1 calc R
C21 C 0.8916(8) 0.0929(4) -0.0627(5) 0.0433(19) Uani 1 1 d .
H21A H 0.9445 0.0607 -0.0250 0.052 Uiso 1 1 calc R
C22 C 0.7968(7) 0.1308(4) -0.0383(4) 0.0350(17) Uani 1 1 d .
C23 C 0.8144(9) 0.0871(4) 0.1734(5) 0.0419(19) Uani 1 1 d .
C24 C 0.8999(9) 0.1278(5) 0.2342(5) 0.053(2) Uani 1 1 d .
C25 C 0.8941(10) 0.1230(6) 0.3152(6) 0.062(3) Uani 1 1 d .
H25A H 0.9481 0.1517 0.3572 0.074 Uiso 1 1 calc R
C26 C 0.8136(11) 0.0785(6) 0.3356(6) 0.065(3) Uani 1 1 d .
H26A H 0.8108 0.0773 0.3923 0.079 Uiso 1 1 calc R
C27 C 0.7335(10) 0.0340(6) 0.2789(7) 0.065(3) Uani 1 1 d .
H27A H 0.6806 0.0016 0.2972 0.078 Uiso 1 1 calc R
C28 C 0.7310(9) 0.0374(4) 0.1905(6) 0.048(2) Uani 1 1 d .
C29 C 0.9967(10) 0.1760(6) 0.2124(7) 0.067(3) Uani 1 1 d .
H29A H 1.0473 0.1998 0.2631 0.100 Uiso 1 1 calc R
H29B H 0.9495 0.2097 0.1711 0.100 Uiso 1 1 calc R
H29C H 1.0562 0.1495 0.1887 0.100 Uiso 1 1 calc R
C30 C 0.6446(10) -0.0058(5) 0.1254(9) 0.075(3) Uani 1 1 d .
H30A H 0.6592 0.0044 0.0709 0.112 Uiso 1 1 calc R
H30B H 0.5532 0.0037 0.1227 0.112 Uiso 1 1 calc R
H30C H 0.6639 -0.0544 0.1391 0.112 Uiso 1 1 calc R
C31 C 0.4246(9) 0.1260(5) 0.0821(6) 0.052(2) Uani 1 1 d .
C32 C 0.3075(10) 0.0869(5) 0.0762(7) 0.058(2) Uani 1 1 d .
H32A H 0.2534 0.0715 0.0235 0.069 Uiso 1 1 calc R
C33 C 0.2772(11) 0.0726(6) 0.1489(7) 0.066(3) Uani 1 1 d .
H33A H 0.1981 0.0486 0.1451 0.080 Uiso 1 1 calc R
C34 C 0.3538(9) 0.0909(5) 0.2275(6) 0.050(2) Uani 1 1 d .
C35 C 0.3134(13) 0.0701(8) 0.3041(8) 0.090(4) Uani 1 1 d .
H35A H 0.2355 0.0409 0.2872 0.134 Uiso 1 1 calc R
H35B H 0.2937 0.1113 0.3323 0.134 Uiso 1 1 calc R
H35C H 0.3849 0.0446 0.3427 0.134 Uiso 1 1 calc R
C36 C 0.4639(9) 0.1328(5) 0.2360(6) 0.055(2) Uani 1 1 d .
H36A H 0.5147 0.1493 0.2891 0.066 Uiso 1 1 calc R
C37 C 0.4958(8) 0.1497(4) 0.1586(6) 0.047(2) 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 0.0033 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'
Ru Ru -1.2594 0.8363 '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
N5 Ru O1 99.3(3)
N5 Ru O2 173.9(3)
O1 Ru O2 86.8(2)
N5 Ru N1 95.3(3)
O1 Ru N1 91.5(3)
O2 Ru N1 84.8(2)
N5 Ru O3 79.7(3)
O1 Ru O3 178.0(2)
O2 Ru O3 94.2(2)
N1 Ru O3 90.3(3)
N5 Ru N3 101.1(3)
O1 Ru N3 83.9(2)
O2 Ru N3 79.1(3)
N1 Ru N3 163.5(3)
O3 Ru N3 94.5(3)
C1 O1 Ru 122.9(5)
C16 O2 Ru 115.3(5)
C31 O3 Ru 112.2(6)
N2 N1 C8 109.1(7)
N2 N1 Ru 129.5(6)
C8 N1 Ru 121.4(5)
N1 N2 C7 119.2(7)
N4 N3 C22 110.6(8)
N4 N3 Ru 136.1(7)
C22 N3 Ru 112.9(5)
N3 N4 C23 113.8(7)
C37 N5 Ru 113.1(6)
O1 C1 C7 125.1(7)
O1 C1 C2 118.6(7)
C7 C1 C2 116.2(7)
C3 C2 C1 122.5(7)
C2 C3 C4 121.4(7)
C6 C4 C3 116.7(7)
C6 C4 C5 122.6(8)
C3 C4 C5 120.6(8)
C4 C6 C7 123.6(7)
C6 C7 C1 119.5(7)
C6 C7 N2 110.6(7)
C1 C7 N2 129.7(7)
C9 C8 C13 122.5(7)
C9 C8 N1 118.0(7)
C13 C8 N1 119.1(7)
C10 C9 C8 118.1(7)
C10 C9 C14 119.6(7)
C8 C9 C14 122.3(7)
C11 C10 C9 120.5(8)
C10 C11 C12 120.7(8)
C13 C12 C11 120.9(8)
C12 C13 C8 117.2(7)
C12 C13 C15 120.0(7)
C8 C13 C15 122.8(7)
O2 C16 C17 121.2(8)
O2 C16 C22 121.5(7)
C17 C16 C22 117.3(7)
C18 C17 C16 120.8(8)
C17 C18 C19 122.8(7)
C21 C19 C18 118.0(7)
C21 C19 C20 120.6(9)
C18 C19 C20 121.3(8)
C19 C21 C22 120.3(8)
C21 C22 C16 120.8(7)
C21 C22 N3 128.4(8)
C16 C22 N3 110.8(7)
C28 C23 C24 124.6(8)
C28 C23 N4 118.4(8)
C24 C23 N4 115.9(8)
C25 C24 C23 118.1(10)
C25 C24 C29 120.2(10)
C23 C24 C29 121.8(8)
C26 C25 C24 120.5(11)
C25 C26 C27 123.6(10)
C26 C27 C28 119.2(9)
C23 C28 C27 113.8(9)
C23 C28 C30 123.3(8)
C27 C28 C30 122.9(9)
O3 C31 C37 117.4(8)
O3 C31 C32 123.4(9)
C37 C31 C32 119.1(9)
C33 C32 C31 117.6(10)
C32 C33 C34 124.2(10)
C33 C34 C36 120.1(8)
C33 C34 C35 119.8(10)
C36 C34 C35 120.0(10)
C34 C36 C37 115.9(9)
C31 C37 N5 115.9(8)
C31 C37 C36 122.7(9)
N5 C37 C36 121.1(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ru N5 1.941(7)
Ru O1 2.009(6)
Ru O2 2.011(6)
Ru N1 2.039(7)
Ru O3 2.059(6)
Ru N3 2.107(8)
O1 C1 1.298(9)
O2 C16 1.307(9)
O3 C31 1.286(11)
N1 N2 1.229(10)
N1 C8 1.468(10)
N2 C7 1.440(10)
N3 N4 1.205(10)
N3 C22 1.434(10)
N4 C23 1.502(11)
N5 C37 1.390(11)
C1 C7 1.411(11)
C1 C2 1.428(11)
C2 C3 1.354(11)
C3 C4 1.408(11)
C4 C6 1.375(11)
C4 C5 1.506(12)
C6 C7 1.399(11)
C8 C9 1.393(10)
C8 C13 1.395(11)
C9 C10 1.391(11)
C9 C14 1.504(11)
C10 C11 1.360(13)
C11 C12 1.393(13)
C12 C13 1.385(10)
C13 C15 1.491(11)
C16 C17 1.402(11)
C16 C22 1.421(12)
C17 C18 1.347(12)
C18 C19 1.402(12)
C19 C21 1.381(11)
C19 C20 1.511(12)
C21 C22 1.399(11)
C23 C28 1.395(12)
C23 C24 1.400(13)
C24 C25 1.366(13)
C24 C29 1.511(14)
C25 C26 1.327(15)
C26 C27 1.383(15)
C27 C28 1.463(13)
C28 C30 1.470(15)
C31 C37 1.362(13)
C31 C32 1.441(13)
C32 C33 1.362(14)
C33 C34 1.377(15)
C34 C36 1.402(13)
C34 C35 1.508(13)
C36 C37 1.456(12)
