#------------------------------------------------------------------------------
#$Date: 2016-03-05 11:59:01 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177827 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/79/7037981.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_7037981
loop_
_publ_author_name
'Tay, Boon Ying'
'Wang, Cun'
'Phua, Pim Huat'
'Stubbs, Ludger Paul'
'Huynh, Han Vinh'
_publ_section_title
;
 Selective hydrogenation of levulinic acid to γ-valerolactone using in
 situ generated ruthenium nanoparticles derived from Ru-NHC complexes.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3558
_journal_page_last               3563
_journal_paper_doi               10.1039/c5dt03366g
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C23 H32 Cl2 N2 Ru'
_chemical_formula_weight         508.48
_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
_audit_update_record
;
2014-04-04 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                87.35(3)
_cell_angle_beta                 84.96(3)
_cell_angle_gamma                71.80(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1962(14)
_cell_length_b                   10.047(2)
_cell_length_c                   16.148(3)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    115.1500
_cell_measurement_theta_max      30.9422
_cell_measurement_theta_min      2.4601
_cell_volume                     1104.6(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      115.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Saturn70 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_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  0.0852
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13014
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         4.982
_refine_diff_density_min         -2.378
_refine_diff_density_rms         0.316
_refine_ls_extinction_coef       0.021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.679
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         5240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.679
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.1282
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3952
_refine_ls_wR_factor_ref         0.4074
_reflns_number_gt                4548
_reflns_number_total             5240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt03366g2.cif
_cod_data_source_block           BY69
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7037980--7037982.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7037981
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
C1 C 0.2111(10) 1.0440(7) 0.4197(4) 0.0377(13) Uani 1 1 d .
C2 C 0.1852(11) 1.1451(8) 0.4813(4) 0.0415(15) Uani 1 1 d .
H2 H 0.1511 1.2401 0.4673 0.050 Uiso 1 1 calc R
C3 C 0.2115(10) 1.1002(8) 0.5621(4) 0.0413(15) Uani 1 1 d .
H3 H 0.1893 1.1657 0.6036 0.050 Uiso 1 1 calc R
C4 C 0.2732(11) 0.9524(8) 0.5837(4) 0.0424(15) Uani 1 1 d .
H4 H 0.2925 0.9245 0.6389 0.051 Uiso 1 1 calc R
C5 C 0.3039(11) 0.8530(9) 0.5246(4) 0.0433(17) Uani 1 1 d .
H5 H 0.3442 0.7579 0.5381 0.052 Uiso 1 1 calc R
C6 C 0.2712(9) 0.9020(7) 0.4414(4) 0.0349(13) Uani 1 1 d .
C7 C 0.2313(10) 0.9224(8) 0.3022(4) 0.0375(13) Uani 1 1 d .
C8 C 0.1522(11) 1.1892(7) 0.2853(4) 0.0404(14) Uani 1 1 d .
H8 H 0.1486 1.1673 0.2271 0.048 Uiso 1 1 calc R
C9 C -0.0437(13) 1.2955(8) 0.3114(5) 0.0505(18) Uani 1 1 d .
H9A H -0.1470 1.2553 0.3068 0.076 Uiso 1 1 calc R
H9B H -0.0640 1.3774 0.2759 0.076 Uiso 1 1 calc R
H9C H -0.0440 1.3211 0.3680 0.076 Uiso 1 1 calc R
C10 C 0.3228(13) 1.2485(9) 0.2896(6) 0.0524(19) Uani 1 1 d .
H10A H 0.3264 1.2757 0.3455 0.079 Uiso 1 1 calc R
H10B H 0.3052 1.3287 0.2530 0.079 Uiso 1 1 calc R
H10C H 0.4440 1.1782 0.2731 0.079 Uiso 1 1 calc R
C11 C 0.3647(11) 0.6774(7) 0.3594(4) 0.0399(14) Uani 1 1 d .
H11 H 0.3623 0.6554 0.3010 0.048 Uiso 1 1 calc R
C12 C 0.5764(12) 0.6258(9) 0.3800(5) 0.0468(16) Uani 1 1 d .
H12A H 0.6504 0.6752 0.3459 0.070 Uiso 1 1 calc R
H12B H 0.6293 0.5272 0.3698 0.070 Uiso 1 1 calc R
H12C H 0.5839 0.6423 0.4375 0.070 Uiso 1 1 calc R
C13 C 0.2366(13) 0.6008(8) 0.4120(5) 0.0497(17) Uani 1 1 d .
H13A H 0.2416 0.6156 0.4700 0.075 Uiso 1 1 calc R
H13B H 0.2855 0.5023 0.4013 0.075 Uiso 1 1 calc R
H13C H 0.1033 0.6373 0.3974 0.075 Uiso 1 1 calc R
C14 C 0.4544(11) 0.9711(10) 0.1320(5) 0.0476(17) Uani 1 1 d .
H14 H 0.4748 1.0464 0.1629 0.057 Uiso 1 1 calc R
C15 C 0.5414(11) 0.8281(10) 0.1580(5) 0.0517(19) Uani 1 1 d .
H15 H 0.6206 0.8078 0.2061 0.062 Uiso 1 1 calc R
C16 C 0.4868(12) 0.7188(10) 0.1244(4) 0.0491(18) Uani 1 1 d .
C17 C 0.3397(11) 0.7552(8) 0.0638(4) 0.0451(16) Uani 1 1 d .
H17 H 0.2813 0.6846 0.0485 0.054 Uiso 1 1 calc R
C18 C 0.2546(11) 0.8961(9) 0.0397(4) 0.0447(16) Uani 1 1 d .
H18 H 0.1384 0.9218 0.0078 0.054 Uiso 1 1 calc R
C19 C 0.2119(13) 1.1584(9) 0.0480(5) 0.058(2) Uani 1 1 d .
H19A H 0.0760 1.1715 0.0414 0.086 Uiso 1 1 calc R
H19B H 0.2743 1.1795 -0.0038 0.086 Uiso 1 1 calc R
H19C H 0.2222 1.2196 0.0900 0.086 Uiso 1 1 calc R
C20 C 0.5935(16) 0.5652(12) 0.1456(5) 0.072(3) Uani 1 1 d .
H20 H 0.6164 0.5589 0.2048 0.087 Uiso 1 1 calc R
C21 C 0.4820(19) 0.4641(10) 0.1305(7) 0.081(4) Uani 1 1 d .
H21A H 0.3529 0.4962 0.1583 0.122 Uiso 1 1 calc R
H21B H 0.5506 0.3727 0.1518 0.122 Uiso 1 1 calc R
H21C H 0.4720 0.4593 0.0719 0.122 Uiso 1 1 calc R
C22 C 0.7976(14) 0.5262(12) 0.0952(6) 0.070(3) Uani 1 1 d .
H22A H 0.8810 0.4393 0.1164 0.105 Uiso 1 1 calc R
H22B H 0.8562 0.5988 0.1004 0.105 Uiso 1 1 calc R
H22C H 0.7810 0.5165 0.0376 0.105 Uiso 1 1 calc R
C23 C 0.3136(12) 1.0043(8) 0.0742(5) 0.0478(17) Uani 1 1 d .
Cl1 Cl -0.1132(3) 1.0504(2) 0.18077(11) 0.0436(5) Uani 1 1 d .
Cl2 Cl 0.0388(3) 0.7165(2) 0.22418(11) 0.0471(5) Uani 1 1 d .
N1 N 0.1879(9) 1.0542(7) 0.3348(4) 0.0385(13) Uani 1 1 d .
N2 N 0.2801(9) 0.8308(6) 0.3667(3) 0.0370(12) Uani 1 1 d .
Ru1 Ru 0.21801(7) 0.88054(6) 0.17837(3) 0.0399(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 0.0033 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
N1 C1 C6 107.3(6)
N1 C1 C2 132.9(6)
C6 C1 C2 119.8(6)
C3 C2 C1 118.5(7)
C2 C3 C4 121.0(6)
C5 C4 C3 121.2(6)
C4 C5 C6 116.9(7)
C1 C6 N2 105.4(6)
C1 C6 C5 122.5(7)
N2 C6 C5 132.1(6)
N2 C7 N1 106.1(6)
N2 C7 Ru1 128.6(5)
N1 C7 Ru1 125.3(5)
N1 C8 C9 112.4(5)
N1 C8 C10 110.4(6)
C9 C8 C10 111.9(6)
N2 C11 C12 112.0(6)
N2 C11 C13 111.0(6)
C12 C11 C13 112.2(6)
C23 C14 C15 120.2(8)
C23 C14 Ru1 72.1(4)
C15 C14 Ru1 70.8(4)
C16 C15 C14 120.5(7)
C16 C15 Ru1 72.2(4)
C14 C15 Ru1 71.5(4)
C15 C16 C17 118.6(8)
C15 C16 C20 120.6(8)
C17 C16 C20 120.6(8)
C15 C16 Ru1 70.6(5)
C17 C16 Ru1 71.1(4)
C20 C16 Ru1 134.6(6)
C18 C17 C16 120.1(8)
C18 C17 Ru1 71.5(4)
C16 C17 Ru1 71.0(4)
C17 C18 C23 120.2(7)
C17 C18 Ru1 71.9(4)
C23 C18 Ru1 71.2(4)
C21 C20 C16 114.8(9)
C21 C20 C22 111.9(9)
C16 C20 C22 106.9(9)
C14 C23 C18 120.4(7)
C14 C23 C19 121.1(8)
C18 C23 C19 118.5(7)
C14 C23 Ru1 71.6(4)
C18 C23 Ru1 71.4(4)
C19 C23 Ru1 127.8(5)
C7 N1 C1 110.2(5)
C7 N1 C8 125.7(6)
C1 N1 C8 123.4(6)
C7 N2 C6 111.0(6)
C7 N2 C11 125.1(6)
C6 N2 C11 123.1(6)
C7 Ru1 C15 90.2(3)
C7 Ru1 C14 94.2(3)
C15 Ru1 C14 37.7(3)
C7 Ru1 C23 122.0(3)
C15 Ru1 C23 66.8(3)
C14 Ru1 C23 36.3(3)
C7 Ru1 C18 159.4(3)
C15 Ru1 C18 79.3(3)
C14 Ru1 C18 66.7(3)
C23 Ru1 C18 37.5(3)
C7 Ru1 C16 113.7(3)
C15 Ru1 C16 37.2(3)
C14 Ru1 C16 67.4(3)
C23 Ru1 C16 79.4(3)
C18 Ru1 C16 67.3(3)
C7 Ru1 C17 151.3(3)
C15 Ru1 C17 67.4(3)
C14 Ru1 C17 79.1(3)
C23 Ru1 C17 66.8(3)
C18 Ru1 C17 36.6(3)
C16 Ru1 C17 37.9(3)
C7 Ru1 Cl2 89.0(2)
C15 Ru1 Cl2 125.7(3)
C14 Ru1 Cl2 163.0(3)
C23 Ru1 Cl2 148.0(2)
C18 Ru1 Cl2 111.5(2)
C16 Ru1 Cl2 95.9(2)
C17 Ru1 Cl2 90.0(2)
C7 Ru1 Cl1 89.49(19)
C15 Ru1 Cl1 151.2(3)
C14 Ru1 Cl1 113.7(2)
C23 Ru1 Cl1 89.2(2)
C18 Ru1 Cl1 91.4(2)
C16 Ru1 Cl1 156.8(2)
C17 Ru1 Cl1 118.9(2)
Cl2 Ru1 Cl1 83.06(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.391(9)
C1 C6 1.393(9)
C1 C2 1.414(9)
C2 C3 1.369(9)
C3 C4 1.446(10)
C4 C5 1.368(11)
C5 C6 1.422(10)
C6 N2 1.417(8)
C7 N2 1.352(9)
C7 N1 1.380(9)
C7 Ru1 2.079(7)
C8 N1 1.504(9)
C8 C9 1.517(10)
C8 C10 1.530(11)
C11 N2 1.476(9)
C11 C12 1.510(11)
C11 C13 1.552(10)
C14 C23 1.391(12)
C14 C15 1.436(13)
C14 Ru1 2.227(7)
C15 C16 1.420(12)
C15 Ru1 2.217(8)
C16 C17 1.456(11)
C16 C20 1.532(13)
C16 Ru1 2.239(8)
C17 C18 1.407(10)
C17 Ru1 2.241(7)
C18 C23 1.435(12)
C18 Ru1 2.236(6)
C19 C23 1.548(11)
C20 C21 1.517(19)
C20 C22 1.560(14)
C23 Ru1 2.233(8)
Cl1 Ru1 2.458(2)
Cl2 Ru1 2.444(2)
