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#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/61/4336168.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_4336168
loop_
_publ_author_name
'Jun Yoshida'
'Go Watanabe'
'Kaori Kakizawa'
'Yasuhiro Kawabata'
'Hidetaka Yuge'
_publ_contact_author_address
;
Department of Chemistry, School of Science, 
Kitasato University, 1-15-1 Kitasato, Minami-ku, 
Sagamihara, Kanagawa, 252-0329, Japan.
;
_publ_contact_author_email       yoshidaj@kitasato-u.ac.jp
_publ_contact_author_fax         '+81 042-778-7980'
_publ_contact_author_name        'Jun Yoshida'
_publ_contact_author_phone       '+81 042-778-9953'
_publ_section_title
;
 Tris(β-diketonato) Ru(III) Complexes as Chiral Dopants for Nematic
 Liquid Crystals: the Effect of the Molecular Structure on the Helical
 Twisting Power
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11042
_journal_page_last               11050
_journal_paper_doi               10.1021/ic401240f
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C39 H33 O6 Ru'
_chemical_formula_sum            'C39 H33 O6 Ru'
_chemical_formula_weight         698.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0982(12)
_cell_length_b                   21.3621(19)
_cell_length_c                   11.9411(10)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4262
_cell_measurement_theta_min      2.4972
_cell_volume                     3341.2(5)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0474
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34547
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             1436
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0506P)²+2.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2745
_reflns_number_total             3812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401240f_si_003.cif
_cod_data_source_block           Ru(acacC2Ph)3
_cod_database_code               4336168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.2614(2) 0.25637(15) 0.9643(3) 0.0386(7) Uani d . 1 C
H1 0.2958 0.2243 0.9192 0.058 Uiso calc R 1 H
H2 0.2546 0.2415 1.0416 0.058 Uiso calc R 1 H
H3 0.3018 0.295 0.9633 0.058 Uiso calc R 1 H
C2 0.1572(2) 0.26908(13) 0.9164(2) 0.0255(6) Uani d . 1 C
C3 0.0937(2) 0.31496(13) 0.9659(2) 0.0248(6) Uani d . 1 C
C4 -0.0057(2) 0.33034(12) 0.9301(2) 0.0252(5) Uani d . 1 C
C5 -0.0630(2) 0.38164(15) 0.9894(3) 0.0370(7) Uani d . 1 C
H4 -0.1306 0.3866 0.9553 0.055 Uiso calc R 1 H
H5 -0.025 0.421 0.9827 0.055 Uiso calc R 1 H
H6 -0.0707 0.3708 1.0687 0.055 Uiso calc R 1 H
O1 0.13420(14) 0.23616(9) 0.83100(15) 0.0260(4) Uani d . 1 O
O2 -0.05428(14) 0.30485(9) 0.85015(15) 0.0274(4) Uani d . 1 O
C6 0.1323(2) 0.35042(13) 1.0588(2) 0.0285(6) Uani d . 1 C
C7 0.1564(2) 0.38299(14) 1.1352(2) 0.0304(6) Uani d . 1 C
C8 0.1795(2) 0.42879(14) 1.2198(2) 0.0307(6) Uani d . 1 C
C9 0.1326(3) 0.48758(16) 1.2135(3) 0.0461(8) Uani d . 1 C
H7 0.0873 0.4965 1.1535 0.055 Uiso calc R 1 H
C10 0.1512(3) 0.53245(17) 1.2932(3) 0.0536(10) Uani d . 1 C
H8 0.1187 0.5721 1.2881 0.064 Uiso calc R 1 H
C11 0.2168(3) 0.51993(17) 1.3803(3) 0.0488(9) Uani d . 1 C
H9 0.2293 0.5509 1.4358 0.059 Uiso calc R 1 H
C12 0.2647(2) 0.46240(16) 1.3874(3) 0.0392(8) Uani d . 1 C
H10 0.3105 0.4542 1.4473 0.047 Uiso calc R 1 H
C13 0.2464(2) 0.41690(15) 1.3079(2) 0.0313(6) Uani d . 1 C
H11 0.2795 0.3774 1.3134 0.038 Uiso calc R 1 H
O3 -0.05080(14) 0.17298(9) 0.85650(14) 0.0258(4) Uani d . 1 O
C14 -0.0782(2) 0.07605(14) 0.9424(2) 0.0349(7) Uani d . 1 C
H12 -0.1063 0.104 0.9997 0.052 Uiso calc R 1 H
H13 -0.0211 0.0522 0.9741 0.052 Uiso calc R 1 H
H14 -0.1314 0.0471 0.9171 0.052 Uiso calc R 1 H
C15 -0.0411(2) 0.11402(13) 0.8449(2) 0.0245(6) Uani d . 1 C
C16 0 0.08327(18) 0.75 0.0255(8) Uani d S 1 C
C17 0 0.0152(2) 0.75 0.0300(8) Uani d S 1 C
C18 0 -0.0391(2) 0.75 0.0361(9) Uani d S 1 C
C19 0 -0.1071(2) 0.75 0.0392(10) Uani d S 1 C
C20 0.0868(3) -0.14018(17) 0.7185(3) 0.0508(9) Uani d . 1 C
H15 0.1468 -0.1183 0.697 0.061 Uiso calc R 1 H
C21 0.0858(4) -0.20571(19) 0.7183(3) 0.0633(12) Uani d . 1 C
H16 0.1449 -0.2282 0.6961 0.076 Uiso calc R 1 H
C22 0 -0.2373(2) 0.75 0.064(2) Uani d S 1 C
H17 0 -0.2817 0.75 0.077 Uiso calc SR 1 H
Ru1 0 0.237758(14) 0.75 0.02111(11) Uani d S 1 Ru
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C2 C1 H1 109.5 . .
C2 C1 H2 109.5 . .
H1 C1 H2 109.5 . .
C2 C1 H3 109.5 . .
H1 C1 H3 109.5 . .
H2 C1 H3 109.5 . .
O1 C2 C3 125.2(2) . .
O1 C2 C1 114.8(2) . .
C3 C2 C1 120.0(2) . .
C4 C3 C2 125.3(2) . .
C4 C3 C6 115.9(2) . .
C2 C3 C6 118.7(2) . .
O2 C4 C3 126.2(2) . .
O2 C4 C5 114.6(2) . .
C3 C4 C5 119.2(2) . .
C4 C5 H4 109.5 . .
C4 C5 H5 109.5 . .
H4 C5 H5 109.5 . .
C4 C5 H6 109.5 . .
H4 C5 H6 109.5 . .
H5 C5 H6 109.5 . .
C2 O1 Ru1 125.69(17) . .
C4 O2 Ru1 125.44(17) . .
C7 C6 C3 174.0(3) . .
C6 C7 C8 172.7(3) . .
C13 C8 C9 118.7(3) . .
C13 C8 C7 122.6(3) . .
C9 C8 C7 118.7(3) . .
C10 C9 C8 120.8(3) . .
C10 C9 H7 119.6 . .
C8 C9 H7 119.6 . .
C9 C10 C11 120.0(3) . .
C9 C10 H8 120 . .
C11 C10 H8 120 . .
C10 C11 C12 120.2(3) . .
C10 C11 H9 119.9 . .
C12 C11 H9 119.9 . .
C13 C12 C11 120.4(3) . .
C13 C12 H10 119.8 . .
C11 C12 H10 119.8 . .
C12 C13 C8 120.0(3) . .
C12 C13 H11 120 . .
C8 C13 H11 120 . .
C15 O3 Ru1 125.74(17) . .
C15 C14 H12 109.5 . .
C15 C14 H13 109.5 . .
H12 C14 H13 109.5 . .
C15 C14 H14 109.5 . .
H12 C14 H14 109.5 . .
H13 C14 H14 109.5 . .
O3 C15 C16 125.7(3) . .
O3 C15 C14 114.8(2) . .
C16 C15 C14 119.6(3) . .
C15 C16 C15 124.7(4) 4_556 .
C15 C16 C17 117.63(18) 4_556 .
C15 C16 C17 117.63(18) . .
C18 C17 C16 180.0000(10) . .
C17 C18 C19 180.0000(10) . .
C20 C19 C20 118.9(5) . 4_556
C20 C19 C18 120.6(2) . .
C20 C19 C18 120.6(2) 4_556 .
C19 C20 C21 120.1(4) . .
C19 C20 H15 120 . .
C21 C20 H15 120 . .
C22 C21 C20 120.1(4) . .
C22 C21 H16 119.9 . .
C20 C21 H16 119.9 . .
C21 C22 C21 120.7(5) . 4_556
C21 C22 H17 119.6 . .
C21 C22 H17 119.6 4_556 .
O3 Ru1 O3 92.09(10) . 4_556
O3 Ru1 O2 177.09(7) . 4_556
O3 Ru1 O2 89.85(8) 4_556 4_556
O3 Ru1 O2 89.85(8) . .
O3 Ru1 O2 177.09(7) 4_556 .
O2 Ru1 O2 88.30(11) 4_556 .
O3 Ru1 O1 90.19(7) . 4_556
O3 Ru1 O1 88.46(8) 4_556 4_556
O2 Ru1 O1 92.03(7) 4_556 4_556
O2 Ru1 O1 89.37(8) . 4_556
O3 Ru1 O1 88.46(8) . .
O3 Ru1 O1 90.19(7) 4_556 .
O2 Ru1 O1 89.37(8) 4_556 .
O2 Ru1 O1 92.03(7) . .
O1 Ru1 O1 178.05(10) 4_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.505(4)
C1 H1 . 0.98
C1 H2 . 0.98
C1 H3 . 0.98
C2 O1 . 1.275(3)
C2 C3 . 1.416(4)
C3 C4 . 1.409(4)
C3 C6 . 1.436(4)
C4 O2 . 1.270(3)
C4 C5 . 1.504(4)
C5 H4 . 0.98
C5 H5 . 0.98
C5 H6 . 0.98
O1 Ru1 . 2.0066(19)
O2 Ru1 . 1.9974(18)
C6 C7 . 1.190(4)
C7 C8 . 1.438(4)
C8 C13 . 1.393(4)
C8 C9 . 1.400(4)
C9 C10 . 1.372(5)
C9 H7 . 0.95
C10 C11 . 1.377(5)
C10 H8 . 0.95
C11 C12 . 1.382(5)
C11 H9 . 0.95
C12 C13 . 1.379(4)
C12 H10 . 0.95
C13 H11 . 0.95
O3 C15 . 1.273(3)
O3 Ru1 . 1.9937(18)
C14 C15 . 1.499(4)
C14 H12 . 0.98
C14 H13 . 0.98
C14 H14 . 0.98
C15 C16 . 1.417(3)
C16 C15 4_556 1.417(3)
C16 C17 . 1.454(6)
C17 C18 . 1.160(6)
C18 C19 . 1.453(6)
C19 C20 . 1.390(4)
C19 C20 4_556 1.390(4)
C20 C21 . 1.400(5)
C20 H15 . 0.95
C21 C22 . 1.364(5)
C21 H16 . 0.95
C22 C21 4_556 1.364(5)
C22 H17 . 0.95
Ru1 O3 4_556 1.9937(18)
Ru1 O2 4_556 1.9973(18)
Ru1 O1 4_556 2.0066(19)
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_4
O1 C2 C3 C4 1.5(4) . .
C1 C2 C3 C4 -178.9(3) . .
O1 C2 C3 C6 -177.0(3) . .
C1 C2 C3 C6 2.6(4) . .
C2 C3 C4 O2 1.6(4) . .
C6 C3 C4 O2 -179.8(3) . .
C2 C3 C4 C5 -178.3(3) . .
C6 C3 C4 C5 0.4(4) . .
C3 C2 O1 Ru1 -3.3(4) . .
C1 C2 O1 Ru1 177.1(2) . .
C3 C4 O2 Ru1 -2.3(4) . .
C5 C4 O2 Ru1 177.54(18) . .
C4 C3 C6 C7 -5(3) . .
C2 C3 C6 C7 174(3) . .
C3 C6 C7 C8 -37(5) . .
C6 C7 C8 C13 -168(2) . .
C6 C7 C8 C9 12(3) . .
C13 C8 C9 C10 -0.6(5) . .
C7 C8 C9 C10 179.1(3) . .
C8 C9 C10 C11 0.1(6) . .
C9 C10 C11 C12 0.5(6) . .
C10 C11 C12 C13 -0.6(5) . .
C11 C12 C13 C8 0.1(4) . .
C9 C8 C13 C12 0.5(4) . .
C7 C8 C13 C12 -179.2(3) . .
Ru1 O3 C15 C16 -5.5(4) . .
Ru1 O3 C15 C14 174.83(18) . .
O3 C15 C16 C15 3.0(2) . 4_556
C14 C15 C16 C15 -177.3(3) . 4_556
O3 C15 C16 C17 -177.0(2) . .
C14 C15 C16 C17 2.7(3) . .
C15 C16 C17 C18 0E1(10) 4_556 .
C15 C16 C17 C18 0E1(10) . .
C16 C17 C18 C19 0E1(10) . .
C17 C18 C19 C20 0E1(10) . .
C17 C18 C19 C20 0E1(10) . 4_556
C20 C19 C20 C21 0.3(3) 4_556 .
C18 C19 C20 C21 -179.7(3) . .
C19 C20 C21 C22 -0.6(5) . .
C20 C21 C22 C21 0.3(3) . 4_556
C15 O3 Ru1 O3 2.65(17) . 4_556
C15 O3 Ru1 O2 -129.1(14) . 4_556
C15 O3 Ru1 O2 -179.5(2) . .
C15 O3 Ru1 O1 91.1(2) . 4_556
C15 O3 Ru1 O1 -87.5(2) . .
C4 O2 Ru1 O3 89.1(2) . .
C4 O2 Ru1 O3 -139.2(14) . 4_556
C4 O2 Ru1 O2 -88.7(2) . 4_556
C4 O2 Ru1 O1 179.3(2) . 4_556
C4 O2 Ru1 O1 0.6(2) . .
C2 O1 Ru1 O3 -87.7(2) . .
C2 O1 Ru1 O3 -179.8(2) . 4_556
C2 O1 Ru1 O2 90.4(2) . 4_556
C2 O1 Ru1 O2 2.1(2) . .
C2 O1 Ru1 O1 -133.8(2) . 4_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139140169
