#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:36:34 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179853 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/49/7014906.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_7014906
loop_
_publ_author_name
'Crimmin, Mark R.'
'Colby, Denise A.'
'Ellman, Jonathan A.'
'Bergman, Robert G.'
_publ_section_title
;
 Synthesis and coordination chemistry of tri-substituted
 benzamidrazones.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              514
_journal_page_last               522
_journal_paper_doi               10.1039/c0dt01267j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C22 H32 Cl N3 Ru'
_chemical_formula_weight         475.03
_chemical_name_common            MRC_II_055A1
_chemical_name_systematic
;
?
;
_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                110.278(5)
_cell_angle_beta                 90.291(5)
_cell_angle_gamma                106.338(5)
_cell_formula_units_Z            2
_cell_length_a                   9.437(5)
_cell_length_b                   10.703(5)
_cell_length_c                   11.940(5)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.74
_cell_volume                     1078.5(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23597
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       dimond
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0257
_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)+(0.0747P)²+0.8069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                3793
_reflns_number_total             3909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0DT01267J.TXT
_cod_data_source_block           compound4a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7014906
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
C1 C 0.3414(3) 0.1913(3) 0.3019(2) 0.0202(5) Uani 1 1 d . . .
C2 C 0.4865(3) 0.1966(3) 0.3357(2) 0.0226(5) Uani 1 1 d . . .
H2 H 0.5623 0.2840 0.3623 0.027 Uiso 1 1 calc R . .
C3 C 0.5218(3) 0.0780(3) 0.3312(3) 0.0276(6) Uani 1 1 d . . .
H3 H 0.6211 0.0853 0.3545 0.033 Uiso 1 1 calc R . .
C4 C 0.4141(3) -0.0513(3) 0.2932(3) 0.0291(6) Uani 1 1 d . . .
H4 H 0.4396 -0.1329 0.2874 0.035 Uiso 1 1 calc R . .
C5 C 0.2682(3) -0.0597(3) 0.2637(3) 0.0255(6) Uani 1 1 d . . .
H5 H 0.1932 -0.1475 0.2382 0.031 Uiso 1 1 calc R . .
C6 C 0.2314(3) 0.0602(3) 0.2715(2) 0.0202(5) Uani 1 1 d . . .
C7 C 0.0814(3) 0.0633(3) 0.2436(2) 0.0205(5) Uani 1 1 d . . .
C8 C -0.1053(3) 0.2962(4) 0.2854(3) 0.0327(7) Uani 1 1 d . . .
H8A H -0.0921 0.2939 0.3660 0.049 Uiso 1 1 calc R . .
H8B H -0.2086 0.2905 0.2663 0.049 Uiso 1 1 calc R . .
H8C H -0.0388 0.3836 0.2827 0.049 Uiso 1 1 calc R . .
C9 C -0.0872(3) 0.1757(3) 0.0760(3) 0.0286(6) Uani 1 1 d . . .
H9A H -0.0626 0.0951 0.0201 0.043 Uiso 1 1 calc R . .
H9B H -0.0205 0.2619 0.0713 0.043 Uiso 1 1 calc R . .
H9C H -0.1903 0.1689 0.0547 0.043 Uiso 1 1 calc R . .
C10 C -0.0737(3) -0.1302(3) 0.3044(2) 0.0235(5) Uani 1 1 d . . .
H10 H 0.0215 -0.1136 0.3523 0.028 Uiso 1 1 calc R . .
C11 C -0.1837(4) -0.0868(4) 0.3909(3) 0.0365(7) Uani 1 1 d . . .
H11A H -0.1437 0.0128 0.4400 0.055 Uiso 1 1 calc R . .
H11B H -0.2001 -0.1415 0.4432 0.055 Uiso 1 1 calc R . .
H11C H -0.2781 -0.1037 0.3452 0.055 Uiso 1 1 calc R . .
C12 C -0.1317(4) -0.2845(3) 0.2265(3) 0.0338(7) Uani 1 1 d . . .
H12A H -0.0588 -0.3098 0.1717 0.051 Uiso 1 1 calc R . .
H12B H -0.2258 -0.3028 0.1797 0.051 Uiso 1 1 calc R . .
H12C H -0.1478 -0.3404 0.2778 0.051 Uiso 1 1 calc R . .
C13 C 0.4977(3) 0.4722(3) 0.2702(2) 0.0212(5) Uani 1 1 d . . .
H13 H 0.5937 0.4731 0.2957 0.025 Uiso 1 1 calc R . .
C14 C 0.4262(3) 0.3785(3) 0.1546(2) 0.0214(5) Uani 1 1 d . . .
C15 C 0.2864(3) 0.3853(3) 0.1176(2) 0.0219(5) Uani 1 1 d . . .
H15 H 0.2336 0.3205 0.0426 0.026 Uiso 1 1 calc R . .
C16 C 0.2238(3) 0.4891(3) 0.1922(3) 0.0240(5) Uani 1 1 d . . .
H16 H 0.1358 0.4988 0.1620 0.029 Uiso 1 1 calc R . .
C17 C 0.2901(3) 0.5758(3) 0.3082(3) 0.0249(6) Uani 1 1 d . . .
C18 C 0.4282(3) 0.5639(3) 0.3477(2) 0.0233(6) Uani 1 1 d . . .
H18 H 0.4734 0.6188 0.4275 0.028 Uiso 1 1 calc R . .
C19 C 0.2151(3) 0.6696(3) 0.3940(3) 0.0316(6) Uani 1 1 d . . .
H19A H 0.2793 0.7218 0.4703 0.047 Uiso 0.50 1 calc PR . .
H19B H 0.1204 0.6131 0.4081 0.047 Uiso 0.50 1 calc PR . .
H19C H 0.1967 0.7353 0.3596 0.047 Uiso 0.50 1 calc PR . .
H19D H 0.1183 0.6584 0.3550 0.047 Uiso 0.50 1 calc PR . .
H19E H 0.2772 0.7670 0.4173 0.047 Uiso 0.50 1 calc PR . .
H19F H 0.2009 0.6448 0.4657 0.047 Uiso 0.50 1 calc PR . .
C20 C 0.5023(3) 0.2779(3) 0.0744(2) 0.0237(5) Uani 1 1 d . . .
H20 H 0.5640 0.2547 0.1282 0.028 Uiso 1 1 calc R . .
C21 C 0.6079(4) 0.3511(3) 0.0045(3) 0.0366(8) Uani 1 1 d . . .
H21A H 0.6570 0.2864 -0.0471 0.055 Uiso 1 1 calc R . .
H21B H 0.6830 0.4329 0.0609 0.055 Uiso 1 1 calc R . .
H21C H 0.5516 0.3809 -0.0453 0.055 Uiso 1 1 calc R . .
C22 C 0.3944(4) 0.1411(3) -0.0089(3) 0.0362(7) Uani 1 1 d . . .
H22A H 0.4502 0.0815 -0.0578 0.054 Uiso 1 1 calc R . .
H22B H 0.3303 0.1604 -0.0616 0.054 Uiso 1 1 calc R . .
H22C H 0.3331 0.0934 0.0389 0.054 Uiso 1 1 calc R . .
N1 N -0.0700(2) 0.1778(2) 0.1976(2) 0.0247(5) Uani 1 1 d . . .
N2 N 0.0788(2) 0.1783(2) 0.22796(19) 0.0197(4) Uani 1 1 d . . .
N3 N -0.0435(3) -0.0448(3) 0.2280(2) 0.0268(5) Uani 1 1 d . . .
Cl Cl 0.20388(7) 0.38633(7) 0.48721(6) 0.02498(17) Uani 1 1 d . . .
Ru Ru 0.273714(18) 0.349751(18) 0.285832(15) 0.01704(11) Uani 1 1 d . . .
H100 H -0.113(4) -0.021(4) 0.211(3) 0.038(10) Uiso 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.4(2) . . ?
C2 C1 Ru 127.1(2) . . ?
C6 C1 Ru 116.49(19) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 C7 124.8(2) . . ?
C1 C6 C7 113.7(2) . . ?
N2 C7 N3 122.4(2) . . ?
N2 C7 C6 113.6(2) . . ?
N3 C7 C6 123.9(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 110.1(2) . . ?
N3 C10 C12 110.1(2) . . ?
C11 C10 C12 111.1(2) . . ?
N3 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C12 C10 H10 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 120.9(2) . . ?
C18 C13 Ru 71.53(15) . . ?
C14 C13 Ru 70.11(14) . . ?
C18 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
Ru C13 H13 131.7 . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C20 122.5(2) . . ?
C13 C14 C20 119.6(2) . . ?
C15 C14 Ru 70.70(15) . . ?
C13 C14 Ru 72.00(15) . . ?
C20 C14 Ru 129.51(19) . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 Ru 71.18(15) . . ?
C16 C15 Ru 75.84(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
Ru C15 H15 125.0 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 Ru 72.72(16) . . ?
C15 C16 Ru 66.66(15) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
Ru C16 H16 134.8 . . ?
C16 C17 C18 117.7(2) . . ?
C16 C17 C19 121.9(3) . . ?
C18 C17 C19 120.2(3) . . ?
C16 C17 Ru 71.90(16) . . ?
C18 C17 Ru 67.83(15) . . ?
C19 C17 Ru 127.1(2) . . ?
C13 C18 C17 121.2(2) . . ?
C13 C18 Ru 71.10(15) . . ?
C17 C18 Ru 75.04(16) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
Ru C18 H18 126.4 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C17 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C17 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C22 C20 C14 113.6(2) . . ?
C22 C20 C21 111.5(3) . . ?
C14 C20 C21 109.4(2) . . ?
C22 C20 H20 107.4 . . ?
C14 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 N1 C9 110.4(2) . . ?
N2 N1 C8 110.7(2) . . ?
C9 N1 C8 112.0(2) . . ?
C7 N2 N1 112.7(2) . . ?
C7 N2 Ru 117.68(17) . . ?
N1 N2 Ru 128.01(17) . . ?
C7 N3 C10 124.6(2) . . ?
C7 N3 H100 107(3) . . ?
C10 N3 H100 115(3) . . ?
C1 Ru N2 76.86(10) . . ?
C1 Ru C15 119.33(10) . . ?
N2 Ru C15 95.99(9) . . ?
C1 Ru C14 92.71(10) . . ?
N2 Ru C14 118.13(10) . . ?
C15 Ru C14 38.12(10) . . ?
C1 Ru C13 94.25(11) . . ?
N2 Ru C13 154.88(10) . . ?
C15 Ru C13 67.63(10) . . ?
C14 Ru C13 37.89(10) . . ?
C1 Ru C18 120.09(11) . . ?
N2 Ru C18 162.48(10) . . ?
C15 Ru C18 79.86(10) . . ?
C14 Ru C18 68.43(10) . . ?
C13 Ru C18 37.38(10) . . ?
C1 Ru C16 156.81(10) . . ?
N2 Ru C16 101.18(10) . . ?
C15 Ru C16 37.50(10) . . ?
C14 Ru C16 67.53(10) . . ?
C13 Ru C16 77.74(10) . . ?
C18 Ru C16 65.24(11) . . ?
C1 Ru C17 157.11(11) . . ?
N2 Ru C17 125.66(10) . . ?
C15 Ru C17 66.92(10) . . ?
C14 Ru C17 80.33(10) . . ?
C13 Ru C17 66.91(10) . . ?
C18 Ru C17 37.13(11) . . ?
C16 Ru C17 35.38(10) . . ?
C1 Ru Cl 85.68(7) . . ?
N2 Ru Cl 86.21(6) . . ?
C15 Ru Cl 154.78(8) . . ?
C14 Ru Cl 154.62(7) . . ?
C13 Ru Cl 116.89(7) . . ?
C18 Ru Cl 90.50(7) . . ?
C16 Ru Cl 117.40(7) . . ?
C17 Ru Cl 91.38(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 C2 1.405(4) . ?
C1 C6 1.415(4) . ?
C1 Ru 2.039(3) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.465(4) . ?
C7 N2 1.315(4) . ?
C7 N3 1.357(4) . ?
C8 N1 1.462(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.451(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N3 1.478(4) . ?
C10 C11 1.519(4) . ?
C10 C12 1.521(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.411(4) . ?
C13 C14 1.420(4) . ?
C13 Ru 2.199(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.418(4) . ?
C14 C20 1.523(4) . ?
C14 Ru 2.174(3) . ?
C15 C16 1.437(4) . ?
C15 Ru 2.168(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(4) . ?
C16 Ru 2.289(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.437(4) . ?
C17 C19 1.501(4) . ?
C17 Ru 2.300(3) . ?
C18 Ru 2.204(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C20 C22 1.520(4) . ?
C20 C21 1.526(4) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 N2 1.446(3) . ?
N2 Ru 2.106(2) . ?
N3 H100 0.82(4) . ?
Cl Ru 2.4244(11) . ?
