#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:31:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178655 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/66/4076601.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_4076601
loop_
_publ_author_name
'O, Wylie W. N.'
'Lough, Alan J.'
'Morris, Robert H.'
_publ_section_title
;
 Factors Favoring Efficient Bifunctional Catalysis. Study of a
 Ruthenium(II) Hydrogenation Catalyst Containing an N-Heterocyclic Carbene
 with a Primary Amine Donor
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              2137
_journal_paper_doi               10.1021/om300108p
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C30 H33 N O P Ru, F6 P'
_chemical_formula_sum            'C30 H33 F6 N O P2 Ru'
_chemical_formula_weight         700.58
_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                 90.204(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3534(3)
_cell_length_b                   15.8749(7)
_cell_length_c                   17.9498(9)
_cell_measurement_reflns_used    15311
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     2950.2(2)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.1292
_diffrn_reflns_av_sigmaI/netI    0.1152
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29905
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.058
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.134
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0586
_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)+(0.0662P)²+0.8063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                3821
_reflns_number_total             6683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om300108p_si_002.cif
_cod_data_source_block           5
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4076601
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.19881(3) 0.03883(2) 0.75211(2) 0.02919(15) Uani 1 1 d . . .
P1 P 0.40058(11) 0.08773(8) 0.78845(7) 0.0292(3) Uani 1 1 d . . .
O1 O 0.3086(3) -0.1355(2) 0.7319(2) 0.0509(10) Uani 1 1 d . . .
N1 N 0.1599(4) 0.0165(3) 0.8689(2) 0.0343(10) Uani 1 1 d . . .
H1C H 0.0948 0.0530 0.8821 0.041 Uiso 1 1 calc R . .
H1D H 0.1261 -0.0369 0.8722 0.041 Uiso 1 1 calc R . .
C1 C 0.2611(4) 0.0231(3) 0.9282(3) 0.0356(12) Uani 1 1 d . . .
H1A H 0.2267 -0.0012 0.9749 0.043 Uiso 1 1 calc R . .
H1B H 0.2795 0.0834 0.9375 0.043 Uiso 1 1 calc R . .
C2 C 0.3875(4) -0.0213(3) 0.9091(3) 0.0295(11) Uani 1 1 d . . .
C3 C 0.4289(4) -0.0871(3) 0.9527(3) 0.0349(12) Uani 1 1 d . . .
H3A H 0.3748 -0.1072 0.9915 0.042 Uiso 1 1 calc R . .
C4 C 0.5489(5) -0.1252(3) 0.9413(3) 0.0375(12) Uani 1 1 d . . .
H4A H 0.5749 -0.1715 0.9713 0.045 Uiso 1 1 calc R . .
C5 C 0.6288(5) -0.0952(3) 0.8867(3) 0.0401(13) Uani 1 1 d . . .
H5A H 0.7123 -0.1189 0.8804 0.048 Uiso 1 1 calc R . .
C6 C 0.5876(4) -0.0299(3) 0.8401(3) 0.0344(12) Uani 1 1 d . . .
H6A H 0.6421 -0.0108 0.8011 0.041 Uiso 1 1 calc R . .
C7 C 0.4669(4) 0.0074(3) 0.8503(3) 0.0307(11) Uani 1 1 d . . .
C8 C 0.4230(4) 0.1827(3) 0.8450(3) 0.0313(11) Uani 1 1 d . . .
C9 C 0.5443(4) 0.2038(3) 0.8729(3) 0.0341(12) Uani 1 1 d . . .
H9A H 0.6167 0.1695 0.8614 0.041 Uiso 1 1 calc R . .
C10 C 0.5603(5) 0.2738(3) 0.9172(3) 0.0384(13) Uani 1 1 d . . .
H10A H 0.6436 0.2876 0.9359 0.046 Uiso 1 1 calc R . .
C11 C 0.4545(5) 0.3248(3) 0.9348(3) 0.0403(13) Uani 1 1 d . . .
H11A H 0.4655 0.3733 0.9651 0.048 Uiso 1 1 calc R . .
C12 C 0.3331(5) 0.3036(3) 0.9075(3) 0.0436(14) Uani 1 1 d . . .
H12A H 0.2603 0.3374 0.9193 0.052 Uiso 1 1 calc R . .
C13 C 0.3182(5) 0.2330(3) 0.8631(3) 0.0367(12) Uani 1 1 d . . .
H13A H 0.2349 0.2188 0.8446 0.044 Uiso 1 1 calc R . .
C14 C 0.5174(4) 0.1022(3) 0.7134(3) 0.0285(11) Uani 1 1 d . . .
C15 C 0.5705(4) 0.1807(3) 0.6977(3) 0.0355(12) Uani 1 1 d . . .
H15A H 0.5484 0.2277 0.7278 0.043 Uiso 1 1 calc R . .
C16 C 0.6554(5) 0.1915(3) 0.6385(3) 0.0399(13) Uani 1 1 d . . .
H16A H 0.6902 0.2455 0.6280 0.048 Uiso 1 1 calc R . .
C17 C 0.6886(5) 0.1231(4) 0.5953(3) 0.0408(13) Uani 1 1 d . . .
H17A H 0.7493 0.1296 0.5561 0.049 Uiso 1 1 calc R . .
C18 C 0.6342(4) 0.0449(3) 0.6086(3) 0.0377(12) Uani 1 1 d . . .
H18A H 0.6556 -0.0016 0.5777 0.045 Uiso 1 1 calc R . .
C19 C 0.5492(4) 0.0346(3) 0.6666(3) 0.0339(12) Uani 1 1 d . . .
H19A H 0.5115 -0.0191 0.6751 0.041 Uiso 1 1 calc R . .
C20 C -0.0031(4) 0.0845(4) 0.7254(3) 0.0433(15) Uani 1 1 d . . .
C21 C 0.0830(5) 0.1498(3) 0.7095(3) 0.0457(15) Uani 1 1 d . . .
C22 C 0.1688(5) 0.1203(4) 0.6527(3) 0.0501(16) Uani 1 1 d . . .
C23 C 0.1344(7) 0.0384(4) 0.6360(3) 0.0585(18) Uani 1 1 d . . .
C24 C 0.0269(6) 0.0142(4) 0.6813(4) 0.0605(19) Uani 1 1 d . . .
C25 C -0.1116(6) 0.0907(7) 0.7818(4) 0.104(3) Uani 1 1 d . . .
H25A H -0.1903 0.1106 0.7570 0.156 Uiso 1 1 calc R . .
H25B H -0.0871 0.1304 0.8213 0.156 Uiso 1 1 calc R . .
H25C H -0.1274 0.0351 0.8037 0.156 Uiso 1 1 calc R . .
C26 C 0.0702(7) 0.2409(4) 0.7326(5) 0.093(3) Uani 1 1 d . . .
H26A H 0.0086 0.2694 0.6996 0.139 Uiso 1 1 calc R . .
H26B H 0.1545 0.2686 0.7292 0.139 Uiso 1 1 calc R . .
H26C H 0.0391 0.2438 0.7841 0.139 Uiso 1 1 calc R . .
C27 C 0.2673(6) 0.1720(6) 0.6118(5) 0.112(4) Uani 1 1 d . . .
H27A H 0.2264 0.1993 0.5688 0.168 Uiso 1 1 calc R . .
H27B H 0.3374 0.1354 0.5947 0.168 Uiso 1 1 calc R . .
H27C H 0.3025 0.2151 0.6453 0.168 Uiso 1 1 calc R . .
C28 C 0.1900(10) -0.0142(7) 0.5735(4) 0.145(5) Uani 1 1 d . . .
H28A H 0.1454 -0.0006 0.5268 0.218 Uiso 1 1 calc R . .
H28B H 0.1782 -0.0741 0.5849 0.218 Uiso 1 1 calc R . .
H28C H 0.2823 -0.0020 0.5685 0.218 Uiso 1 1 calc R . .
C29 C -0.0509(9) -0.0658(5) 0.6761(7) 0.166(6) Uani 1 1 d . . .
H29A H -0.1243 -0.0571 0.6424 0.249 Uiso 1 1 calc R . .
H29B H -0.0827 -0.0810 0.7257 0.249 Uiso 1 1 calc R . .
H29C H 0.0036 -0.1113 0.6569 0.249 Uiso 1 1 calc R . .
C30 C 0.2703(5) -0.0693(4) 0.7425(3) 0.0356(12) Uani 1 1 d . . .
P2 P -0.03548(13) 0.18947(10) 1.00374(9) 0.0425(4) Uani 1 1 d . . .
F1 F 0.0381(7) 0.2127(4) 0.9285(4) 0.105(3) Uani 0.874(12) 1 d P A 1
F2 F -0.1672(5) 0.2124(4) 0.9672(4) 0.101(2) Uani 0.874(12) 1 d P A 1
F3 F -0.1095(7) 0.1639(3) 1.0775(3) 0.090(2) Uani 0.874(12) 1 d P A 1
F4 F 0.0977(6) 0.1677(4) 1.0393(4) 0.115(3) Uani 0.874(12) 1 d P A 1
F1A F 0.089(2) 0.2007(16) 0.9679(18) 0.034(8) Uiso 0.126(12) 1 d P A 2
F2A F -0.110(4) 0.239(2) 0.9438(18) 0.060(11) Uiso 0.126(12) 1 d P A 2
F3A F -0.171(2) 0.1766(18) 1.041(2) 0.046(9) Uiso 0.126(12) 1 d P A 2
F4A F 0.025(4) 0.137(2) 1.0717(18) 0.064(11) Uiso 0.126(12) 1 d P A 2
F5 F -0.0500(3) 0.0960(2) 0.9724(2) 0.0752(11) Uani 1 1 d . A .
F6 F -0.0211(3) 0.2820(2) 1.0359(3) 0.0835(13) Uani 1 1 d . A .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C30 Ru1 N1 90.82(19)
C30 Ru1 C23 91.6(2)
N1 Ru1 C23 149.9(2)
C30 Ru1 C24 95.8(2)
N1 Ru1 C24 112.0(2)
C23 Ru1 C24 38.0(3)
C30 Ru1 C22 120.8(2)
N1 Ru1 C22 147.7(2)
C23 Ru1 C22 36.5(2)
C24 Ru1 C22 62.2(2)
C30 Ru1 C21 152.8(2)
N1 Ru1 C21 110.76(18)
C23 Ru1 C21 61.4(2)
C24 Ru1 C21 61.4(2)
C22 Ru1 C21 37.2(2)
C30 Ru1 C20 129.7(2)
N1 Ru1 C20 94.73(16)
C23 Ru1 C20 61.3(2)
C24 Ru1 C20 36.5(2)
C22 Ru1 C20 61.15(19)
C21 Ru1 C20 36.0(2)
C30 Ru1 P1 88.66(15)
N1 Ru1 P1 87.31(11)
C23 Ru1 P1 122.7(2)
C24 Ru1 P1 160.0(2)
C22 Ru1 P1 98.86(15)
C21 Ru1 P1 108.06(14)
C20 Ru1 P1 141.50(17)
C7 P1 C14 106.7(2)
C7 P1 C8 101.1(2)
C14 P1 C8 102.8(2)
C7 P1 Ru1 105.88(16)
C14 P1 Ru1 115.59(15)
C8 P1 Ru1 122.90(16)
C1 N1 Ru1 123.0(3)
N1 C1 C2 114.0(4)
C3 C2 C7 119.3(4)
C3 C2 C1 119.3(4)
C7 C2 C1 121.3(4)
C2 C3 C4 121.4(5)
C5 C4 C3 119.6(5)
C4 C5 C6 120.1(5)
C7 C6 C5 120.5(5)
C6 C7 C2 119.0(4)
C6 C7 P1 123.5(4)
C2 C7 P1 117.4(3)
C13 C8 C9 118.8(5)
C13 C8 P1 120.4(4)
C9 C8 P1 120.7(4)
C10 C9 C8 120.6(5)
C9 C10 C11 120.3(5)
C12 C11 C10 119.2(5)
C13 C12 C11 119.9(5)
C12 C13 C8 121.1(5)
C15 C14 C19 118.1(4)
C15 C14 P1 121.7(4)
C19 C14 P1 120.1(4)
C14 C15 C16 121.0(5)
C17 C16 C15 119.5(5)
C16 C17 C18 120.4(5)
C19 C18 C17 119.9(5)
C18 C19 C14 121.0(5)
C21 C20 C24 109.3(5)
C21 C20 C25 124.3(7)
C24 C20 C25 126.4(7)
C21 C20 Ru1 72.0(3)
C24 C20 Ru1 70.0(3)
C25 C20 Ru1 124.4(4)
C20 C21 C22 107.5(5)
C20 C21 C26 126.6(6)
C22 C21 C26 124.3(6)
C20 C21 Ru1 72.1(3)
C22 C21 Ru1 69.9(3)
C26 C21 Ru1 134.4(4)
C23 C22 C21 107.6(5)
C23 C22 C27 125.7(7)
C21 C22 C27 126.3(7)
C23 C22 Ru1 70.3(3)
C21 C22 Ru1 72.8(3)
C27 C22 Ru1 128.1(4)
C22 C23 C24 109.3(5)
C22 C23 C28 125.6(8)
C24 C23 C28 124.8(8)
C22 C23 Ru1 73.3(3)
C24 C23 Ru1 72.3(3)
C28 C23 Ru1 126.3(4)
C20 C24 C23 106.3(5)
C20 C24 C29 125.8(8)
C23 C24 C29 127.4(8)
C20 C24 Ru1 73.5(3)
C23 C24 Ru1 69.8(3)
C29 C24 Ru1 127.7(4)
O1 C30 Ru1 174.9(5)
F1A P2 F2A 94.0(16)
F2 P2 F4 178.9(4)
F1A P2 F3A 178.9(15)
F2A P2 F3A 85.3(15)
F2 P2 F6 91.0(3)
F4 P2 F6 88.6(3)
F2 P2 F3 89.2(3)
F4 P2 F3 91.8(4)
F6 P2 F3 88.8(2)
F2 P2 F5 89.3(3)
F4 P2 F5 91.1(3)
F6 P2 F5 179.3(3)
F3 P2 F5 90.6(2)
F2 P2 F1 90.5(3)
F4 P2 F1 88.5(4)
F6 P2 F1 92.8(3)
F3 P2 F1 178.4(3)
F5 P2 F1 87.8(3)
F1A P2 F4A 93.4(15)
F2A P2 F4A 172.5(17)
F3A P2 F4A 87.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ru1 C30 1.877(6)
Ru1 N1 2.166(4)
Ru1 C23 2.186(6)
Ru1 C24 2.218(5)
Ru1 C22 2.224(5)
Ru1 C21 2.262(5)
Ru1 C20 2.263(5)
Ru1 P1 2.3200(12)
P1 C7 1.823(5)
P1 C14 1.828(5)
P1 C8 1.832(5)
O1 C30 1.140(6)
N1 C1 1.495(6)
C1 C2 1.526(6)
C2 C3 1.374(7)
C2 C7 1.416(6)
C3 C4 1.397(7)
C4 C5 1.371(7)
C5 C6 1.398(7)
C6 C7 1.395(6)
C8 C13 1.386(6)
C8 C9 1.392(7)
C9 C10 1.376(7)
C10 C11 1.399(7)
C11 C12 1.389(7)
C12 C13 1.383(7)
C14 C15 1.391(6)
C14 C19 1.403(7)
C15 C16 1.392(7)
C16 C17 1.379(7)
C17 C18 1.384(7)
C18 C19 1.375(6)
C20 C21 1.397(8)
C20 C24 1.405(9)
C20 C25 1.518(7)
C21 C22 1.433(8)
C21 C26 1.511(8)
C22 C23 1.381(9)
C22 C27 1.504(8)
C23 C24 1.432(9)
C23 C28 1.514(9)
C24 C29 1.506(9)
P2 F1A 1.45(2)
P2 F2A 1.54(3)
P2 F2 1.554(5)
P2 F4 1.556(4)
P2 F3A 1.57(3)
P2 F6 1.585(4)
P2 F3 1.585(5)
P2 F5 1.594(4)
P2 F1 1.596(5)
P2 F4A 1.60(3)
