#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:51:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178537 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/43/4064353.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_4064353
loop_
_publ_author_name
'Zhang, Congying'
'Li, Bin'
'Song, Haibin'
'Xu, Shansheng'
'Wang, Baiquan'
_publ_section_title
;
 Reactions of Unsymmetrically Substituted N-Heterocyclic Carbenes with
 Ru3(CO)12
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3029
_journal_paper_doi               10.1021/om2000647
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C13 H9 I N2 O3 Ru'
_chemical_formula_sum            'C13 H9 I N2 O3 Ru'
_chemical_formula_weight         469.19
_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                 93.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.124(6)
_cell_length_b                   10.143(9)
_cell_length_c                   19.925(14)
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.3
_cell_volume                     1436(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.2125
_diffrn_reflns_av_sigmaI/netI    0.2940
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7964
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    3.248
_exptl_absorpt_correction_T_max  0.6966
_exptl_absorpt_correction_T_min  0.6246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         3.429
_refine_diff_density_min         -2.542
_refine_diff_density_rms         0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.718
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      0.714
_refine_ls_R_factor_all          0.1688
_refine_ls_R_factor_gt           0.0851
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1948P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2897
_reflns_number_gt                945
_reflns_number_total             2483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2000647_si_001.cif
_cod_data_source_block           complex_1
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4064353
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
I1 I -0.02156(15) 0.16469(11) 0.11168(6) 0.0335(5) Uani 1 1 d .
Ru1 Ru 0.34402(18) 0.28395(13) 0.15248(8) 0.0273(5) Uani 1 1 d .
N1 N 0.2610(18) 0.4736(13) 0.0414(7) 0.023(3) Uani 1 1 d U
N2 N 0.336(2) 0.2995(14) -0.0049(7) 0.027(3) Uani 1 1 d U
O1 O 0.7251(17) 0.4318(12) 0.1972(6) 0.033(3) Uani 1 1 d .
O2 O 0.340(2) 0.2406(13) 0.3007(7) 0.040(3) Uani 1 1 d .
O3 O 0.5003(18) 0.0025(12) 0.1398(6) 0.038(3) Uani 1 1 d U
C1 C 0.587(2) 0.3725(17) 0.1840(9) 0.027(4) Uani 1 1 d U
C2 C 0.340(2) 0.2521(17) 0.2453(10) 0.027(4) Uani 1 1 d .
C3 C 0.449(2) 0.1072(18) 0.1433(8) 0.027(4) Uani 1 1 d U
C4 C 0.229(2) 0.4763(17) 0.1533(9) 0.026(4) Uani 1 1 d U
C5 C 0.177(2) 0.5470(17) 0.2034(10) 0.031(4) Uani 1 1 d .
H5 H 0.1753 0.5065 0.2463 0.037 Uiso 1 1 calc R
C6 C 0.124(2) 0.6788(15) 0.1973(9) 0.024(4) Uani 1 1 d .
H6 H 0.0849 0.7218 0.2363 0.028 Uiso 1 1 calc R
C7 C 0.123(3) 0.7506(18) 0.1394(10) 0.038(5) Uani 1 1 d .
H7 H 0.0910 0.8415 0.1375 0.046 Uiso 1 1 calc R
C8 C 0.172(2) 0.6832(16) 0.0857(9) 0.026(4) Uani 1 1 d U
H8 H 0.1757 0.7253 0.0432 0.032 Uiso 1 1 calc R
C9 C 0.218(2) 0.5455(15) 0.0934(8) 0.021(3) Uani 1 1 d U
C10 C 0.249(2) 0.5067(19) -0.0250(9) 0.032(4) Uani 1 1 d U
H10 H 0.2149 0.5885 -0.0456 0.039 Uiso 1 1 calc R
C11 C 0.295(2) 0.3995(17) -0.0518(10) 0.030(4) Uani 1 1 d .
H11 H 0.3019 0.3883 -0.0989 0.036 Uiso 1 1 calc R
C12 C 0.316(2) 0.3454(15) 0.0542(9) 0.022(4) Uani 1 1 d .
C13 C 0.385(3) 0.1649(16) -0.0150(11) 0.036(5) Uani 1 1 d .
H13A H 0.5075 0.1464 0.0084 0.054 Uiso 1 1 calc R
H13B H 0.3913 0.1480 -0.0632 0.054 Uiso 1 1 calc R
H13C H 0.2892 0.1078 0.0029 0.054 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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C2 Ru1 C3 88.1(7)
C2 Ru1 C1 80.8(7)
C3 Ru1 C1 96.5(7)
C2 Ru1 C12 169.9(7)
C3 Ru1 C12 101.6(6)
C1 Ru1 C12 100.9(7)
C2 Ru1 C4 96.8(7)
C3 Ru1 C4 175.1(7)
C1 Ru1 C4 84.8(6)
C12 Ru1 C4 73.5(6)
C2 Ru1 I1 97.4(5)
C3 Ru1 I1 86.1(5)
C1 Ru1 I1 176.7(5)
C12 Ru1 I1 80.4(4)
C4 Ru1 I1 92.7(4)
C9 N1 C10 128.6(15)
C9 N1 C12 117.0(14)
C10 N1 C12 114.3(15)
C12 N2 C11 108.6(15)
C12 N2 C13 121.3(15)
C11 N2 C13 130.0(16)
O1 C1 Ru1 173.6(16)
O2 C2 Ru1 176.0(16)
O3 C3 Ru1 176.0(15)
C5 C4 C9 112.1(17)
C5 C4 Ru1 130.2(14)
C9 C4 Ru1 117.5(12)
C4 C5 C6 123.6(19)
C4 C5 H5 118.2
C6 C5 H5 118.2
C7 C6 C5 124.9(17)
C7 C6 H6 117.6
C5 C6 H6 117.6
C8 C7 C6 114.7(17)
C8 C7 H7 122.6
C6 C7 H7 122.6
C7 C8 C9 118.7(16)
C7 C8 H8 120.6
C9 C8 H8 120.6
N1 C9 C4 113.2(14)
N1 C9 C8 121.1(16)
C4 C9 C8 125.7(16)
C11 C10 N1 101.4(16)
C11 C10 H10 129.3
N1 C10 H10 129.3
C10 C11 N2 113.0(18)
C10 C11 H11 123.5
N2 C11 H11 123.5
N2 C12 N1 102.8(15)
N2 C12 Ru1 139.1(13)
N1 C12 Ru1 118.2(12)
N2 C13 H13A 109.5
N2 C13 H13B 109.5
H13A C13 H13B 109.5
N2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 Ru1 2.935(3)
Ru1 C2 1.88(2)
Ru1 C3 1.955(18)
Ru1 C1 2.012(19)
Ru1 C12 2.052(18)
Ru1 C4 2.115(17)
N1 C9 1.32(2)
N1 C10 1.36(2)
N1 C12 1.38(2)
N2 C12 1.28(2)
N2 C11 1.40(2)
N2 C13 1.43(2)
O1 C1 1.17(2)
O2 C2 1.11(2)
O3 C3 1.13(2)
C4 C5 1.30(2)
C4 C9 1.38(2)
C5 C6 1.39(2)
C5 H5 0.9500
C6 C7 1.36(3)
C6 H6 0.9500
C7 C8 1.34(2)
C7 H7 0.9500
C8 C9 1.44(2)
C8 H8 0.9500
C10 C11 1.27(3)
C10 H10 0.9500
C11 H11 0.9500
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 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
C2 Ru1 C1 O1 -150(13)
C3 Ru1 C1 O1 123(13)
C12 Ru1 C1 O1 20(13)
C4 Ru1 C1 O1 -52(13)
I1 Ru1 C1 O1 -93(16)
C3 Ru1 C2 O2 146(24)
C1 Ru1 C2 O2 49(24)
C12 Ru1 C2 O2 -51(26)
C4 Ru1 C2 O2 -34(24)
I1 Ru1 C2 O2 -128(24)
C2 Ru1 C3 O3 54(23)
C1 Ru1 C3 O3 134(23)
C12 Ru1 C3 O3 -123(23)
C4 Ru1 C3 O3 -120(22)
I1 Ru1 C3 O3 -44(23)
C2 Ru1 C4 C5 0.7(17)
C3 Ru1 C4 C5 174(7)
C1 Ru1 C4 C5 -79.3(17)
C12 Ru1 C4 C5 177.8(17)
I1 Ru1 C4 C5 98.6(16)
C2 Ru1 C4 C9 175.5(13)
C3 Ru1 C4 C9 -11(8)
C1 Ru1 C4 C9 95.5(13)
C12 Ru1 C4 C9 -7.5(12)
I1 Ru1 C4 C9 -86.6(12)
C9 C4 C5 C6 -3(2)
Ru1 C4 C5 C6 172.3(13)
C4 C5 C6 C7 -1(3)
C5 C6 C7 C8 3(3)
C6 C7 C8 C9 0(2)
C10 N1 C9 C4 174.0(16)
C12 N1 C9 C4 -2(2)
C10 N1 C9 C8 -9(2)
C12 N1 C9 C8 175.6(14)
C5 C4 C9 N1 -176.8(15)
Ru1 C4 C9 N1 7.5(18)
C5 C4 C9 C8 6(2)
Ru1 C4 C9 C8 -169.9(12)
C7 C8 C9 N1 178.0(16)
C7 C8 C9 C4 -5(3)
C9 N1 C10 C11 -175.8(16)
C12 N1 C10 C11 0.2(18)
N1 C10 C11 N2 0.1(19)
C12 N2 C11 C10 0(2)
C13 N2 C11 C10 176.8(17)
C11 N2 C12 N1 0.4(17)
C13 N2 C12 N1 -177.1(14)
C11 N2 C12 Ru1 -178.6(13)
C13 N2 C12 Ru1 4(3)
C9 N1 C12 N2 176.1(14)
C10 N1 C12 N2 -0.4(18)
C9 N1 C12 Ru1 -4.7(18)
C10 N1 C12 Ru1 178.9(11)
C2 Ru1 C12 N2 -158(3)
C3 Ru1 C12 N2 5.0(19)
C1 Ru1 C12 N2 104.0(18)
C4 Ru1 C12 N2 -174.7(19)
I1 Ru1 C12 N2 -79.0(18)
C2 Ru1 C12 N1 23(4)
C3 Ru1 C12 N1 -173.9(11)
C1 Ru1 C12 N1 -74.9(12)
C4 Ru1 C12 N1 6.4(11)
I1 Ru1 C12 N1 102.1(11)
