#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:35:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180228 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/14/7111417.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111417
loop_
_publ_author_name
'Munslow, Ian J.'
'Wade, Andrew R.'
'Deeth, Robert J.'
'Scott, Peter'
_publ_section_title
;
 Aminooxazolinate; a chiral amidinate analogue
;
_journal_issue                   22
_journal_name_full               'Chemical Communications'
_journal_page_first              2596
_journal_page_last               2597
_journal_paper_doi               10.1039/b409113b
_journal_year                    2004
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C19 H23 Cl N2 O Ru'
_chemical_formula_weight         431.91
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1427(4)
_cell_length_b                   11.1134(4)
_cell_length_c                   16.1543(6)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      2.72
_cell_volume                     1820.91(12)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Siemens SMART diffractometer'
_diffrn_measurement_method       'ω 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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11618
_diffrn_reflns_theta_full        28.90
_diffrn_reflns_theta_max         28.90
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.927992
_exptl_absorpt_correction_T_min  0.711182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0368
_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)+(0.0243P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3368
_reflns_number_total             4368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b409113bsup1.cif
_cod_data_source_block           arw1m_(SRu,SC)-[Ru(eta-C6H6)L1Cl]
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7111417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.53573(3) 0.27803(3) 0.877269(19) 0.02367(8) Uani 1 1 d .
Cl1 Cl 0.57963(11) 0.18298(9) 0.74676(6) 0.0378(3) Uani 1 1 d .
N1 N 0.4590(4) 0.1063(2) 0.91505(17) 0.0244(7) Uani 1 1 d .
O1 O 0.2752(3) 0.0311(2) 0.85102(16) 0.0305(7) Uani 1 1 d .
C4 C 0.2325(4) 0.2875(4) 0.7997(2) 0.0254(8) Uani 1 1 d .
C5 C 0.1137(4) 0.2276(4) 0.7819(2) 0.0319(9) Uani 1 1 d .
H5A H 0.1000 0.1486 0.8026 0.038 Uiso 1 1 calc R
C6 C 0.0170(4) 0.2815(4) 0.7351(2) 0.0365(9) Uani 1 1 d .
H6A H -0.0624 0.2392 0.7238 0.044 Uiso 1 1 calc R
C10 C 0.5448(4) -0.0816(3) 0.9875(2) 0.0304(9) Uani 1 1 d .
C12 C 0.5455(5) -0.2178(4) 0.9780(3) 0.0487(11) Uani 1 1 d .
H12A H 0.4548 -0.2481 0.9804 0.073 Uiso 1 1 calc R
H12B H 0.5972 -0.2538 1.0228 0.073 Uiso 1 1 calc R
H12C H 0.5848 -0.2393 0.9246 0.073 Uiso 1 1 calc R
C3 C 0.3503(4) 0.1281(3) 0.8726(3) 0.0255(8) Uani 1 1 d .
C7 C 0.0342(5) 0.3973(4) 0.7043(2) 0.0387(10) Uani 1 1 d .
H7A H -0.0331 0.4341 0.6721 0.046 Uiso 1 1 calc R
C8 C 0.1494(4) 0.4581(4) 0.7208(3) 0.0362(11) Uani 1 1 d .
H8A H 0.1621 0.5369 0.6996 0.043 Uiso 1 1 calc R
N2 N 0.3321(3) 0.2408(3) 0.84942(18) 0.0240(7) Uani 1 1 d .
C1 C 0.4818(4) -0.0251(3) 0.9103(2) 0.0243(9) Uani 1 1 d .
H1A H 0.5393 -0.0423 0.8614 0.029 Uiso 1 1 calc R
C9 C 0.2478(4) 0.4040(4) 0.7687(2) 0.0305(10) Uani 1 1 d .
H9A H 0.3264 0.4472 0.7804 0.037 Uiso 1 1 calc R
C11 C 0.6902(4) -0.0397(5) 0.9923(3) 0.0510(13) Uani 1 1 d .
H11A H 0.7336 -0.0790 1.0393 0.077 Uiso 1 1 calc R
H11B H 0.6931 0.0478 0.9998 0.077 Uiso 1 1 calc R
H11C H 0.7358 -0.0614 0.9410 0.077 Uiso 1 1 calc R
C2 C 0.3410(4) -0.0700(3) 0.8913(3) 0.0371(11) Uani 1 1 d .
H2A H 0.3435 -0.1408 0.8541 0.044 Uiso 1 1 calc R
H2B H 0.2947 -0.0925 0.9430 0.044 Uiso 1 1 calc R
C13 C 0.4769(6) -0.0438(4) 1.0672(2) 0.0514(13) Uani 1 1 d .
H13A H 0.3852 -0.0717 1.0666 0.077 Uiso 1 1 calc R
H13B H 0.4786 0.0441 1.0720 0.077 Uiso 1 1 calc R
H13C H 0.5230 -0.0794 1.1146 0.077 Uiso 1 1 calc R
C100 C 0.5209(5) 0.4000(4) 0.9834(3) 0.0474(12) Uani 1 1 d .
H10A H 0.4410 0.3975 1.0196 0.057 Uiso 1 1 calc R
C101 C 0.5197(5) 0.4677(4) 0.9127(3) 0.0410(12) Uani 1 1 d .
H10B H 0.4364 0.5111 0.8984 0.049 Uiso 1 1 calc R
C102 C 0.6151(5) 0.4583(4) 0.8522(3) 0.0386(12) Uani 1 1 d .
H10C H 0.6012 0.4966 0.7969 0.046 Uiso 1 1 calc R
C103 C 0.7189(4) 0.3769(4) 0.8638(3) 0.0478(13) Uani 1 1 d .
H10D H 0.7779 0.3578 0.8159 0.057 Uiso 1 1 calc R
C105 C 0.6239(6) 0.3160(4) 0.9959(3) 0.0554(15) Uani 1 1 d .
H10E H 0.6170 0.2556 1.0416 0.067 Uiso 1 1 calc R
C104 C 0.7267(5) 0.3049(4) 0.9355(4) 0.0581(16) Uani 1 1 d .
H10G H 0.7916 0.2373 0.9388 0.070 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
N1 Ru1 N2 62.71(12) y
N1 Ru1 C105 94.10(15) ?
N2 Ru1 C105 128.38(18) ?
N1 Ru1 C103 142.01(18) ?
N2 Ru1 C103 153.85(17) ?
C105 Ru1 C103 68.6(2) ?
N1 Ru1 C104 108.76(17) ?
N2 Ru1 C104 166.19(19) ?
C105 Ru1 C104 38.6(2) ?
C103 Ru1 C104 37.89(19) ?
N1 Ru1 C100 107.61(14) ?
N2 Ru1 C100 102.50(16) ?
C105 Ru1 C100 38.02(18) ?
C103 Ru1 C100 79.87(18) ?
C104 Ru1 C100 68.8(2) ?
N1 Ru1 C101 138.89(16) ?
N2 Ru1 C101 99.69(15) ?
C105 Ru1 C101 67.08(18) ?
C103 Ru1 C101 66.59(18) ?
C104 Ru1 C101 79.69(18) ?
C100 Ru1 C101 36.37(15) ?
N1 Ru1 C102 174.11(14) ?
N2 Ru1 C102 119.23(15) ?
C105 Ru1 C102 80.40(16) ?
C103 Ru1 C102 37.42(17) ?
C104 Ru1 C102 68.16(18) ?
C100 Ru1 C102 66.72(16) ?
C101 Ru1 C102 36.64(16) ?
N1 Ru1 Cl1 85.74(8) y
N2 Ru1 Cl1 84.83(8) y
C105 Ru1 Cl1 142.17(18) ?
C103 Ru1 Cl1 88.61(13) ?
C104 Ru1 Cl1 105.98(17) ?
C100 Ru1 Cl1 166.56(13) ?
C101 Ru1 Cl1 131.83(13) ?
C102 Ru1 Cl1 99.89(12) ?
N1 Ru1 C3 31.68(12) ?
N2 Ru1 C3 31.68(11) ?
C105 Ru1 C3 117.80(17) ?
C103 Ru1 C3 166.76(15) ?
C104 Ru1 C3 140.39(17) ?
C100 Ru1 C3 112.46(16) ?
C101 Ru1 C3 126.16(16) ?
C102 Ru1 C3 150.84(15) ?
Cl1 Ru1 C3 79.68(10) ?
C3 N1 C1 106.6(3) ?
C3 N1 Ru1 89.5(2) ?
C1 N1 Ru1 143.5(3) ?
C3 O1 C2 103.8(3) ?
N2 C4 C9 118.2(4) ?
N2 C4 C5 124.3(4) ?
C9 C4 C5 117.4(4) ?
C6 C5 C4 121.1(4) ?
C6 C5 H5A 119.4 ?
C4 C5 H5A 119.4 ?
C5 C6 C7 120.7(4) ?
C5 C6 H6A 119.7 ?
C7 C6 H6A 119.7 ?
C13 C10 C12 111.2(3) ?
C13 C10 C1 112.8(3) ?
C12 C10 C1 109.0(3) ?
C13 C10 C11 107.8(4) ?
C12 C10 C11 107.5(4) ?
C1 C10 C11 108.3(3) ?
C10 C12 H12A 109.5 ?
C10 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C10 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N2 C3 N1 116.0(3) ?
N2 C3 O1 126.7(4) ?
N1 C3 O1 117.0(3) ?
N2 C3 Ru1 58.98(19) ?
N1 C3 Ru1 58.80(18) ?
O1 C3 Ru1 161.5(3) ?
C8 C7 C6 119.5(4) ?
C8 C7 H7A 120.3 ?
C6 C7 H7A 120.3 ?
C7 C8 C9 120.1(4) ?
C7 C8 H8A 119.9 ?
C9 C8 H8A 119.9 ?
C3 N2 C4 128.3(3) ?
C3 N2 Ru1 89.3(2) ?
C4 N2 Ru1 138.2(2) ?
N1 C1 C10 115.2(3) ?
N1 C1 C2 100.6(3) ?
C10 C1 C2 114.5(3) ?
N1 C1 H1A 108.7 ?
C10 C1 H1A 108.7 ?
C2 C1 H1A 108.7 ?
C4 C9 C8 121.2(4) ?
C4 C9 H9A 119.4 ?
C8 C9 H9A 119.4 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O1 C2 C1 105.2(3) ?
O1 C2 H2A 110.7 ?
C1 C2 H2A 110.7 ?
O1 C2 H2B 110.7 ?
C1 C2 H2B 110.7 ?
H2A C2 H2B 108.8 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C101 C100 C105 119.3(5) ?
C101 C100 Ru1 71.8(2) ?
C105 C100 Ru1 69.7(2) ?
C101 C100 H10A 119.8 ?
C105 C100 H10A 119.8 ?
Ru1 C100 H10A 119.8 ?
C100 C101 C102 122.9(5) ?
C100 C101 Ru1 71.8(2) ?
C102 C101 Ru1 71.9(2) ?
C100 C101 H10B 117.8 ?
C102 C101 H10B 117.8 ?
Ru1 C101 H10B 117.8 ?
C101 C102 C103 118.8(4) ?
C101 C102 Ru1 71.4(2) ?
C103 C102 Ru1 70.2(2) ?
C101 C102 H10C 120.1 ?
C103 C102 H10C 120.1 ?
Ru1 C102 H10C 120.1 ?
C102 C103 C104 121.2(4) ?
C102 C103 Ru1 72.3(2) ?
C104 C103 Ru1 71.2(3) ?
C102 C103 H10D 118.8 ?
C104 C103 H10D 118.8 ?
Ru1 C103 H10D 118.8 ?
C100 C105 C104 119.7(4) ?
C100 C105 Ru1 72.3(2) ?
C104 C105 Ru1 71.3(3) ?
C100 C105 H10E 119.8 ?
C104 C105 H10E 119.8 ?
Ru1 C105 H10E 119.8 ?
C103 C104 C105 118.0(4) ?
C103 C104 Ru1 70.9(3) ?
C105 C104 Ru1 70.0(3) ?
C103 C104 H10G 120.4 ?
C105 C104 H10G 120.4 ?
Ru1 C104 H10G 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ru1 N1 2.150(3) y
Ru1 N2 2.154(3) y
Ru1 C105 2.157(4) y
Ru1 C103 2.170(4) y
Ru1 C104 2.174(4) y
Ru1 C100 2.190(4) y
Ru1 C101 2.190(4) y
Ru1 C102 2.197(4) y
Ru1 Cl1 2.3997(11) y
Ru1 C3 2.514(4) ?
N1 C3 1.320(5) ?
N1 C1 1.480(4) ?
O1 C3 1.365(4) ?
O1 C2 1.460(5) ?
C4 N2 1.391(5) ?
C4 C9 1.396(6) ?
C4 C5 1.407(5) ?
C5 C6 1.376(5) ?
C5 H5A 0.9500 ?
C6 C7 1.391(6) ?
C6 H6A 0.9500 ?
C10 C13 1.520(6) ?
C10 C12 1.522(5) ?
C10 C1 1.536(5) ?
C10 C11 1.548(6) ?
C12 H12A 0.9800 ?
C12 H12B 0.9800 ?
C12 H12C 0.9800 ?
C3 N2 1.320(4) ?
C7 C8 1.375(6) ?
C7 H7A 0.9500 ?
C8 C9 1.399(6) ?
C8 H8A 0.9500 ?
C1 C2 1.544(6) ?
C1 H1A 1.0000 ?
C9 H9A 0.9500 ?
C11 H11A 0.9800 ?
C11 H11B 0.9800 ?
C11 H11C 0.9800 ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C13 H13A 0.9800 ?
C13 H13B 0.9800 ?
C13 H13C 0.9800 ?
C100 C101 1.367(6) ?
C100 C105 1.416(7) ?
C100 H10A 1.0000 ?
C101 C102 1.379(6) ?
C101 H10B 1.0000 ?
C102 C103 1.401(6) ?
C102 H10C 1.0000 ?
C103 C104 1.410(7) ?
C103 H10D 1.0000 ?
C105 C104 1.433(8) ?
C105 H10E 1.0000 ?
C104 H10G 1.0000 ?
