#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:22:11 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179324 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/21/4322100.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_4322100
loop_
_publ_author_name
'Matti Haukka'
'Pipsa Hirva'
'Saija Luukkanen'
'Mirja Kallinen'
'Markku Ahlgrén'
'Tapani A. Pakkanen'
_publ_contact_author
;
        Matti Haukka
        Department of Chemistry
        University of Joensuu
        PO Box 111, FIN-80101
        Finland
;
_publ_contact_author_email       matti.haukka@joensuu.fi
_publ_contact_author_fax         358-13-2513344
_publ_contact_author_phone       358-13-2513345
_publ_section_title
;
 Reactions of Ruthenium Bipyridine Catalyst Precursors: Synthetic,
 Structural, and Theoretical Studies on Ruthenium Mono(bipyridine)
 Carbonyls in Ethylene Glycol Solutions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3182
_journal_page_last               3189
_journal_paper_doi               10.1021/ic981266y
_journal_volume                  38
_journal_year                    1999
_chemical_formula_sum            'C12 H9 Cl N2 O2 Ru'
_chemical_formula_weight         349.73
_chemical_name_common            Ru(bpy)(CO)2ClH
_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                89.20(3)
_cell_angle_beta                 81.37(3)
_cell_angle_gamma                81.20(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3871(10)
_cell_length_b                   8.132(2)
_cell_length_c                   12.693(3)
_cell_measurement_temperature    293(2)
_cell_volume                     644.1(3)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski, Minor, 1997)'
_computing_data_collection       'kcd (Nonius B.V., 1997)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski, Minor, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2126
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    1.418
_exptl_crystal_colour            'Brownish yellow'
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0055(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0355
_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
'w=1/[σ²(Fo²)+(0.0222P)²+0.2687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                1853
_reflns_number_total             2126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic981266y_3.cif
_cod_data_source_block           Ru(bpy)(CO)2ClH
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+0.2687P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+0.2687P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        644.2(2)
_cod_database_code               4322100
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru Ru 0.63170(4) 0.63350(3) 0.81238(2) 0.04116(13) Uani 1 d . . .
Cl1 Cl 0.45557(13) 0.74429(10) 0.65540(6) 0.0483(2) Uani 1 d . . .
C1 C 0.4374(6) 0.7495(4) 0.9197(3) 0.0539(9) Uani 1 d . . .
O1 O 0.3213(5) 0.8170(4) 0.9890(2) 0.0779(8) Uani 1 d . . .
C2 C 0.8037(6) 0.7959(5) 0.8198(3) 0.0571(9) Uani 1 d . . .
O2 O 0.9118(5) 0.8928(4) 0.8282(3) 0.0941(11) Uani 1 d . . .
N1 N 0.8470(4) 0.4729(3) 0.7021(2) 0.0401(6) Uani 1 d . . .
N2 N 0.4726(4) 0.4240(3) 0.8063(2) 0.0419(6) Uani 1 d . . .
C10 C 1.0385(5) 0.5039(5) 0.6513(3) 0.0459(8) Uani 1 d . . .
C11 C 1.1686(6) 0.3968(5) 0.5797(3) 0.0547(9) Uani 1 d . . .
C12 C 1.1049(6) 0.2507(5) 0.5571(3) 0.0646(10) Uani 1 d . . .
C13 C 0.9114(6) 0.2157(5) 0.6077(3) 0.0618(10) Uani 1 d . . .
C14 C 0.7846(5) 0.3269(4) 0.6807(3) 0.0436(7) Uani 1 d . . .
C15 C 0.5782(5) 0.2981(4) 0.7411(3) 0.0432(7) Uani 1 d . . .
C16 C 0.4935(6) 0.1517(4) 0.7330(3) 0.0551(9) Uani 1 d . . .
C17 C 0.3006(6) 0.1352(5) 0.7937(4) 0.0616(10) Uani 1 d . . .
C18 C 0.1941(6) 0.2614(5) 0.8586(3) 0.0579(10) Uani 1 d . . .
C19 C 0.2839(6) 0.4043(5) 0.8629(3) 0.0491(8) Uani 1 d . . .
H10 H 1.065(5) 0.597(4) 0.667(3) 0.047(10) Uiso 1 d . . .
H11 H 1.295(5) 0.430(4) 0.546(2) 0.043(9) Uiso 1 d . . .
H12 H 1.192(7) 0.173(6) 0.507(4) 0.093(14) Uiso 1 d . . .
H13 H 0.864(7) 0.123(6) 0.598(4) 0.091(15) Uiso 1 d . . .
H16 H 0.572(6) 0.072(5) 0.681(3) 0.077(13) Uiso 1 d . . .
H17 H 0.244(6) 0.050(5) 0.787(3) 0.068(12) Uiso 1 d . . .
H18 H 0.065(5) 0.254(4) 0.900(3) 0.047(9) Uiso 1 d . . .
H19 H 0.223(6) 0.483(5) 0.905(3) 0.052(11) Uiso 1 d . . .
H5 H 0.754(5) 0.541(4) 0.910(2) 0.052(9) Uiso 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'
Ru Ru -1.2594 0.8363 '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'
O O 0.0106 0.0060 '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
C2 Ru C1 87.46(15) . . ?
C2 Ru N1 97.72(13) . . ?
C1 Ru N1 172.44(13) . . ?
C2 Ru N2 172.17(13) . . ?
C1 Ru N2 97.31(12) . . ?
N1 Ru N2 76.96(10) . . ?
C2 Ru Cl1 98.49(13) . . ?
C1 Ru Cl1 98.21(12) . . ?
N1 Ru Cl1 86.52(7) . . ?
N2 Ru Cl1 87.01(8) . . ?
C2 Ru H5 85.4(11) . . ?
C1 Ru H5 86.4(11) . . ?
N1 Ru H5 88.5(11) . . ?
N2 Ru H5 88.7(11) . . ?
Cl1 Ru H5 174.0(11) . . ?
O1 C1 Ru 177.2(3) . . ?
O2 C2 Ru 177.2(4) . . ?
C14 N1 C10 117.7(3) . . ?
C14 N1 Ru 116.3(2) . . ?
C10 N1 Ru 125.9(2) . . ?
C19 N2 C15 118.3(3) . . ?
C19 N2 Ru 126.0(2) . . ?
C15 N2 Ru 115.67(19) . . ?
N1 C10 C11 123.3(3) . . ?
N1 C10 H10 112(2) . . ?
C11 C10 H10 124(2) . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 118(2) . . ?
C12 C11 H11 123(2) . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 H12 121(3) . . ?
C13 C12 H12 120(3) . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 123(3) . . ?
C14 C13 H13 116(3) . . ?
N1 C14 C13 120.7(3) . . ?
N1 C14 C15 115.1(3) . . ?
C13 C14 C15 124.2(3) . . ?
N2 C15 C16 121.0(3) . . ?
N2 C15 C14 115.9(3) . . ?
C16 C15 C14 123.1(3) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16 125(3) . . ?
C15 C16 H16 116(3) . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120(3) . . ?
C16 C17 H17 120(3) . . ?
C17 C18 C19 118.6(4) . . ?
C17 C18 H18 122(2) . . ?
C19 C18 H18 119(2) . . ?
N2 C19 C18 123.0(4) . . ?
N2 C19 H19 117(2) . . ?
C18 C19 H19 120(2) . . ?
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
Ru C2 1.854(4) . ?
Ru C1 1.859(4) . ?
Ru N1 2.117(3) . ?
Ru N2 2.121(3) . ?
Ru Cl1 2.5219(11) . ?
Ru H5 1.67(3) . ?
C1 O1 1.148(4) . ?
C2 O2 1.140(4) . ?
N1 C14 1.353(4) . ?
N1 C10 1.353(4) . ?
N2 C19 1.338(4) . ?
N2 C15 1.354(4) . ?
C10 C11 1.360(5) . ?
C10 H10 0.83(3) . ?
C11 C12 1.361(5) . ?
C11 H11 0.93(3) . ?
C12 C13 1.373(5) . ?
C12 H12 0.95(5) . ?
C13 C14 1.381(5) . ?
C13 H13 0.87(5) . ?
C14 C15 1.471(4) . ?
C15 C16 1.392(5) . ?
C16 C17 1.376(5) . ?
C16 H16 0.96(4) . ?
C17 C18 1.355(6) . ?
C17 H17 0.84(4) . ?
C18 C19 1.378(5) . ?
C18 H18 0.92(3) . ?
C19 H19 0.84(4) . ?
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
C2 Ru C1 O1 -94(6) . . . . ?
N1 Ru C1 O1 39(7) . . . . ?
N2 Ru C1 O1 80(6) . . . . ?
Cl1 Ru C1 O1 168(6) . . . . ?
C1 Ru C2 O2 76(7) . . . . ?
N1 Ru C2 O2 -99(7) . . . . ?
N2 Ru C2 O2 -52(7) . . . . ?
Cl1 Ru C2 O2 174(7) . . . . ?
C2 Ru N1 C14 175.1(2) . . . . ?
C1 Ru N1 C14 42.2(10) . . . . ?
N2 Ru N1 C14 1.0(2) . . . . ?
Cl1 Ru N1 C14 -86.8(2) . . . . ?
C2 Ru N1 C10 -5.4(3) . . . . ?
C1 Ru N1 C10 -138.3(9) . . . . ?
N2 Ru N1 C10 -179.5(3) . . . . ?
Cl1 Ru N1 C10 92.8(3) . . . . ?
C2 Ru N2 C19 130.7(9) . . . . ?
C1 Ru N2 C19 3.5(3) . . . . ?
N1 Ru N2 C19 178.5(3) . . . . ?
Cl1 Ru N2 C19 -94.4(3) . . . . ?
C2 Ru N2 C15 -47.1(10) . . . . ?
C1 Ru N2 C15 -174.3(2) . . . . ?
N1 Ru N2 C15 0.7(2) . . . . ?
Cl1 Ru N2 C15 87.8(2) . . . . ?
C14 N1 C10 C11 0.7(5) . . . . ?
Ru N1 C10 C11 -178.8(3) . . . . ?
N1 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C10 N1 C14 C13 -1.3(5) . . . . ?
Ru N1 C14 C13 178.3(3) . . . . ?
C10 N1 C14 C15 178.1(3) . . . . ?
Ru N1 C14 C15 -2.4(4) . . . . ?
C12 C13 C14 N1 1.2(6) . . . . ?
C12 C13 C14 C15 -178.1(4) . . . . ?
C19 N2 C15 C16 -0.1(5) . . . . ?
Ru N2 C15 C16 177.9(3) . . . . ?
C19 N2 C15 C14 179.9(3) . . . . ?
Ru N2 C15 C14 -2.2(4) . . . . ?
N1 C14 C15 N2 3.0(4) . . . . ?
C13 C14 C15 N2 -177.7(3) . . . . ?
N1 C14 C15 C16 -177.0(3) . . . . ?
C13 C14 C15 C16 2.3(6) . . . . ?
N2 C15 C16 C17 -0.9(5) . . . . ?
C14 C15 C16 C17 179.1(3) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C15 N2 C19 C18 0.8(5) . . . . ?
Ru N2 C19 C18 -176.9(3) . . . . ?
C17 C18 C19 N2 -0.4(6) . . . . ?
