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#$Date: 2016-03-21 14:01:21 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178709 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/20/4082074.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_4082074
loop_
_publ_author_name
'Nagarajaprakash, R.'
'Ramakrishna, Buthanapalli'
'Mahesh, K.'
'Mobin, Shaikh M.'
'Manimaran, Bala.'
_publ_section_title
;
 One-Pot Synthesis of Ruthenium Metallacycles via Oxidative Addition of
 Diaryldichalcogen and Halogen across a Ru--Ru Bond
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7292
_journal_paper_doi               10.1021/om400686q
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C20 H14 Br2 O6 Ru2 Se2'
_chemical_formula_sum            'C20 H14 Br2 O6 Ru2 Se2'
_chemical_formula_weight         870.20
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-10-31
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep  7 2011 21:07:27, GUI svn.r3853)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9490(4)
_cell_length_b                   18.4754(6)
_cell_length_c                   8.9862(2)
_cell_measurement_reflns_used    13351
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.6289
_cell_measurement_theta_min      3.1542
_cell_volume                     2647.91(12)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       ω/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18978
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.939
_exptl_absorpt_correction_T_max  0.4657
_exptl_absorpt_correction_T_min  0.2983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0165
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0241P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0380
_refine_ls_wR_factor_ref         0.0387
_reflns_number_gt                2075
_reflns_number_total             2404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400686q_si_002.cif
_cod_data_source_block           7
_cod_database_code               4082074
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, 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
Ru1 Ru 0.813259(16) 0.2500 0.56638(3) 0.01880(8) Uani 1 2 d S
Ru2 Ru 0.941322(17) 0.2500 0.21112(3) 0.01909(8) Uani 1 2 d S
Br1 Br 0.67683(2) 0.2500 0.42317(4) 0.03099(10) Uani 1 2 d S
Br2 Br 0.81503(2) 0.2500 0.03819(4) 0.03077(11) Uani 1 2 d S
Se1 Se 0.861684(15) 0.160390(14) 0.36986(2) 0.01996(7) Uani 1 1 d .
O1 O 0.97831(16) 0.2500 0.7310(3) 0.0331(6) Uani 1 2 d S
O2 O 0.73057(12) 0.36942(12) 0.7518(2) 0.0426(5) Uani 1 1 d .
O3 O 1.00835(12) 0.12770(11) 0.0161(2) 0.0379(5) Uani 1 1 d .
O4 O 1.08445(15) 0.2500 0.4317(3) 0.0329(7) Uani 1 2 d S
C1 C 0.9170(2) 0.2500 0.6692(4) 0.0225(8) Uani 1 2 d S
C2 C 0.76376(16) 0.32553(15) 0.6866(3) 0.0272(6) Uani 1 1 d .
C3 C 0.98630(16) 0.17358(15) 0.0884(3) 0.0257(6) Uani 1 1 d .
C4 C 1.0319(2) 0.2500 0.3470(4) 0.0233(8) Uani 1 2 d S
C5 C 0.94826(15) 0.09703(14) 0.4581(3) 0.0249(6) Uani 1 1 d .
H5A H 0.9767 0.0694 0.3784 0.030 Uiso 1 1 calc R
H5B H 0.9908 0.1270 0.5095 0.030 Uiso 1 1 calc R
C6 C 0.90973(15) 0.04594(15) 0.5659(3) 0.0246(6) Uani 1 1 d .
C7 C 0.85626(17) -0.00877(17) 0.5197(3) 0.0334(7) Uani 1 1 d .
H7 H 0.8436 -0.0138 0.4169 0.040 Uiso 1 1 calc R
C8 C 0.82137(18) -0.05592(17) 0.6206(3) 0.0423(8) Uani 1 1 d .
H8 H 0.7852 -0.0935 0.5875 0.051 Uiso 1 1 calc R
C9 C 0.83903(18) -0.04856(18) 0.7703(3) 0.0429(8) Uani 1 1 d .
H9 H 0.8151 -0.0812 0.8402 0.052 Uiso 1 1 calc R
C10 C 0.89090(19) 0.00556(18) 0.8181(3) 0.0403(7) Uani 1 1 d .
H10 H 0.9024 0.0107 0.9213 0.048 Uiso 1 1 calc R
C11 C 0.92681(16) 0.05286(16) 0.7171(3) 0.0303(6) Uani 1 1 d .
H11 H 0.9632 0.0901 0.7510 0.036 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
Br1 Ru1 Se1 84.711(11) . .
Br1 Ru1 Se1 84.711(11) . 8_565
Se1 Ru1 Se1 81.321(14) 8_565 .
C1 Ru1 Br1 178.56(10) . .
C1 Ru1 Se1 94.20(7) . 8_565
C1 Ru1 Se1 94.20(7) . .
C1 Ru1 C2 94.83(10) . .
C1 Ru1 C2 94.83(10) . 8_565
C2 Ru1 Br1 86.16(7) . .
C2 Ru1 Br1 86.16(7) 8_565 .
C2 Ru1 Se1 92.43(8) 8_565 .
C2 Ru1 Se1 169.37(7) . .
C2 Ru1 Se1 169.37(7) 8_565 8_565
C2 Ru1 Se1 92.43(8) . 8_565
C2 Ru1 C2 92.39(15) . 8_565
Se1 Ru2 Br2 86.955(11) . .
Se1 Ru2 Br2 86.955(11) 8_565 .
Se1 Ru2 Se1 81.837(14) . 8_565
C3 Ru2 Br2 86.86(7) 8_565 .
C3 Ru2 Br2 86.86(7) . .
C3 Ru2 Se1 91.73(8) 8_565 8_565
C3 Ru2 Se1 171.30(8) . 8_565
C3 Ru2 Se1 171.30(8) 8_565 .
C3 Ru2 Se1 91.73(8) . .
C3 Ru2 C3 94.03(15) 8_565 .
C4 Ru2 Br2 177.45(10) . .
C4 Ru2 Se1 91.12(7) . 8_565
C4 Ru2 Se1 91.12(7) . .
C4 Ru2 C3 94.88(10) . 8_565
C4 Ru2 C3 94.88(10) . .
Ru2 Se1 Ru1 96.789(11) . .
C5 Se1 Ru1 108.62(7) . .
C5 Se1 Ru2 105.27(7) . .
O1 C1 Ru1 179.5(3) . .
O2 C2 Ru1 175.8(2) . .
O3 C3 Ru2 176.4(2) . .
O4 C4 Ru2 178.0(3) . .
Se1 C5 H5A 109.6 . .
Se1 C5 H5B 109.6 . .
H5A C5 H5B 108.1 . .
C6 C5 Se1 110.43(16) . .
C6 C5 H5A 109.6 . .
C6 C5 H5B 109.6 . .
C7 C6 C5 121.5(2) . .
C7 C6 C11 118.7(2) . .
C11 C6 C5 119.8(2) . .
C6 C7 H7 119.6 . .
C8 C7 C6 120.9(2) . .
C8 C7 H7 119.6 . .
C7 C8 H8 120.1 . .
C7 C8 C9 119.8(3) . .
C9 C8 H8 120.1 . .
C8 C9 H9 119.9 . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 119.9 . .
C9 C10 H10 119.8 . .
C9 C10 C11 120.4(3) . .
C11 C10 H10 119.8 . .
C6 C11 H11 120.0 . .
C10 C11 C6 120.1(3) . .
C10 C11 H11 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 Br1 2.5281(4) .
Ru1 Se1 2.5409(3) 8_565
Ru1 Se1 2.5409(3) .
Ru1 C1 1.895(4) .
Ru1 C2 1.933(3) .
Ru1 C2 1.933(3) 8_565
Ru2 Br2 2.5440(4) .
Ru2 Se1 2.5277(3) 8_565
Ru2 Se1 2.5277(3) .
Ru2 C3 1.930(3) .
Ru2 C3 1.930(3) 8_565
Ru2 C4 1.892(4) .
Se1 C5 1.976(2) .
O1 C1 1.125(4) .
O2 C2 1.131(3) .
O3 C3 1.124(3) .
O4 C4 1.132(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.485(3) .
C6 C7 1.386(4) .
C6 C11 1.391(3) .
C7 H7 0.9500 .
C7 C8 1.375(4) .
C8 H8 0.9500 .
C8 C9 1.381(4) .
C9 H9 0.9500 .
C9 C10 1.367(4) .
C10 H10 0.9500 .
C10 C11 1.385(4) .
C11 H11 0.9500 .
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
Ru1 Se1 C5 C6 71.87(18) .
Ru2 Se1 C5 C6 174.66(15) .
Br1 Ru1 Se1 Ru2 99.085(11) .
Br1 Ru1 Se1 C5 -152.25(8) .
Br1 Ru1 C1 O1 180.00(6) .
Br1 Ru1 C2 O2 -1(3) .
Br2 Ru2 Se1 Ru1 -101.057(11) .
Br2 Ru2 Se1 C5 147.48(8) .
Br2 Ru2 C3 O3 -37(4) .
Br2 Ru2 C4 O4 -0.001(8) .
Se1 Ru1 Se1 Ru2 13.646(13) 8_565
Se1 Ru1 Se1 C5 122.31(8) 8_565
Se1 Ru1 C1 O1 139.20(6) 8_565
Se1 Ru1 C1 O1 -139.21(7) .
Se1 Ru1 C2 O2 30(4) .
Se1 Ru1 C2 O2 84(3) 8_565
Se1 Ru2 Se1 Ru1 -13.700(13) 8_565
Se1 Ru2 Se1 C5 -125.16(8) 8_565
Se1 Ru2 C3 O3 7(4) 8_565
Se1 Ru2 C3 O3 50(4) .
Se1 Ru2 C4 O4 -40.928(9) .
Se1 Ru2 C4 O4 40.927(9) 8_565
Se1 C5 C6 C7 67.9(3) .
Se1 C5 C6 C11 -111.7(2) .
C1 Ru1 Se1 Ru2 -79.97(6) .
C1 Ru1 Se1 C5 28.69(10) .
C1 Ru1 C2 O2 178(100) .
C2 Ru1 Se1 Ru2 -175.00(7) 8_565
C2 Ru1 Se1 Ru2 68.1(4) .
C2 Ru1 Se1 C5 176.8(4) .
C2 Ru1 Se1 C5 -66.34(11) 8_565
C2 Ru1 C1 O1 -46.41(10) 8_565
C2 Ru1 C1 O1 46.40(10) .
C2 Ru1 C2 O2 -86(3) 8_565
C3 Ru2 Se1 Ru1 172.18(7) .
C3 Ru2 Se1 Ru1 -56.3(5) 8_565
C3 Ru2 Se1 C5 60.72(11) .
C3 Ru2 Se1 C5 -167.8(5) 8_565
C3 Ru2 C3 O3 -124(4) 8_565
C3 Ru2 C4 O4 132.76(8) 8_565
C3 Ru2 C4 O4 -132.76(8) .
C4 Ru2 Se1 Ru1 77.27(6) .
C4 Ru2 Se1 C5 -34.19(10) .
C4 Ru2 C3 O3 141(4) .
C5 C6 C7 C8 179.7(3) .
C5 C6 C11 C10 179.8(2) .
C6 C7 C8 C9 0.6(5) .
C7 C6 C11 C10 0.2(4) .
C7 C8 C9 C10 0.2(5) .
C8 C9 C10 C11 -0.7(5) .
C9 C10 C11 C6 0.5(5) .
C11 C6 C7 C8 -0.7(4) .
