# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_maku082_p-1
_database_code_depnum_ccdc_archive 'CCDC 1468156'
_audit_update_record             
;
2016-03-15 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
'Chlorido[2-Butyl-(3-oxo-?O)-[1,4]-naphthoquinonato- ?O4] ](h6-p-cymene)ruthenium(II)'
_chemical_formula_moiety         'C24 H27 Cl O3 Ru'
_chemical_formula_sum            'C24 H27 Cl O3 Ru'
_chemical_formula_weight         499.97
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3210(15)
_cell_length_b                   15.229(3)
_cell_length_c                   17.358(3)
_cell_angle_alpha                93.711(6)
_cell_angle_beta                 92.771(5)
_cell_angle_gamma                91.845(5)
_cell_volume                     2454.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7914
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.709
_cell_measurement_theta_min      2.631
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.7551.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41883
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.189
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6789
_reflns_number_total             8736
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         8736
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+0.7093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12A ∼ C12A-C13C ∼ C13D-C12B ∼ C13B-C12B
 with sigma of 0.01
 C14A-C13A ∼ C14B-C13B ∼ C14D-C13D
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C13A) = Uanis(C13C) = Uanis(C13D) = Uanis(C13B)
Uanis(C14C) = Uanis(C14A) = Uanis(C14B) = Uanis(C14D)
4. Others
 Sof(H12C)=Sof(H12D)=Sof(H12G)=Sof(H12H)=Sof(C13C)=Sof(H13C)=Sof(H13D)=
 Sof(C13D)=Sof(H13G)=Sof(H13H)=Sof(C14D)=Sof(H14J)=Sof(H14K)=Sof(H14L)=
 Sof(C14C)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(C13B)=Sof(H13E)=
 Sof(H13F)=Sof(C14B)=Sof(H14G)=Sof(H14H)=Sof(H14I)=Sof(H12E)=Sof(H12F)=
 Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C21A(H21A), C21B(H21B)
5.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C12A(H12A,H12B), C12A(H12C,H12D), C11B(H11C,H11D), C13A(H13A,
 H13B), C13B(H13E,H13F), C12B(H12E,H12F), C12B(H12G,H12H), C13C(H13C,H13D),
 C13D(H13G,H13H)
5.c Aromatic/amide H refined with riding coordinates:
 C20A(H20A), C16A(H16A), C19A(H19A), C17A(H17A), C6A(H6A), C7A(H7A), C9A(H9A),
 C8A(H8A), C20B(H20B), C16B(H16B), C17B(H17B), C19B(H19B), C6B(H6B), C9B(H9B),
 C7B(H7B), C8B(H8B)
5.d Idealised Me refined as rotating group:
 C22A(H22A,H22B,H22C), C24A(H24A,H24B,H24C), C23A(H23A,H23B,H23C), C24B(H24D,
 H24E,H24F), C23B(H23D,H23E,H23F), C22B(H22D,H22E,H22F), C14B(H14G,H14H,H14I),
 C14A(H14A,H14B,H14C), C14D(H14J,H14K,H14L), C14C(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1A Ru 0.93924(3) 0.76345(2) 1.07271(2) 0.01727(9) Uani 1 1 d . . . . .
Cl1A Cl 0.71720(9) 0.79592(6) 1.00719(5) 0.0225(2) Uani 1 1 d . . . . .
Ru1B Ru 0.52814(3) -0.03532(2) 0.27145(2) 0.01715(9) Uani 1 1 d . . . . .
Cl1B Cl 0.75403(8) 0.03793(6) 0.25457(5) 0.0220(2) Uani 1 1 d . . . . .
O2B O 0.5177(2) 0.05148(15) 0.36662(13) 0.0216(6) Uani 1 1 d . . . . .
O1B O 0.6435(2) -0.09779(15) 0.35981(13) 0.0218(6) Uani 1 1 d . . . . .
O3B O 0.8036(2) 0.13737(16) 0.59087(14) 0.0256(6) Uani 1 1 d . . . . .
O2A O 0.9568(2) 0.66577(15) 0.98660(14) 0.0225(6) Uani 1 1 d . . . . .
O1A O 0.8181(2) 0.65575(15) 1.11169(14) 0.0203(6) Uani 1 1 d . . . . .
O3A O 0.7167(2) 0.40475(15) 0.88590(15) 0.0276(6) Uani 1 1 d . . . . .
C15A C 1.1138(3) 0.8506(2) 1.0432(2) 0.0171(8) Uani 1 1 d . . . . .
C20A C 1.1680(3) 0.7793(2) 1.0840(2) 0.0181(8) Uani 1 1 d . . . . .
H20A H 1.2395 0.7440 1.0618 0.022 Uiso 1 1 calc R . . . .
C21A C 1.1595(3) 0.8720(2) 0.9643(2) 0.0203(8) Uani 1 1 d . . . . .
H21A H 1.0756 0.8983 0.9374 0.024 Uiso 1 1 calc R . . . .
C18A C 1.0086(3) 0.8105(2) 1.1898(2) 0.0225(9) Uani 1 1 d . . . . .
C22A C 1.2811(3) 0.9430(2) 0.9732(2) 0.0252(9) Uani 1 1 d . . . . .
H22A H 1.2515 0.9929 1.0066 0.038 Uiso 1 1 calc GR . . . .
H22B H 1.3018 0.9631 0.9222 0.038 Uiso 1 1 calc GR . . . .
H22C H 1.3676 0.9183 0.9963 0.038 Uiso 1 1 calc GR . . . .
C16A C 1.0062(3) 0.9001(2) 1.0787(2) 0.0202(8) Uani 1 1 d . . . . .
H16A H 0.9669 0.9476 1.0528 0.024 Uiso 1 1 calc R . . . .
C19A C 1.1180(3) 0.7603(2) 1.1561(2) 0.0200(8) Uani 1 1 d . . . . .
H19A H 1.1576 0.7134 1.1827 0.024 Uiso 1 1 calc R . . . .
C17A C 0.9556(4) 0.8814(2) 1.1511(2) 0.0243(9) Uani 1 1 d . . . . .
H17A H 0.8850 0.9170 1.1738 0.029 Uiso 1 1 calc R . . . .
C24A C 0.9469(4) 0.7849(3) 1.2634(2) 0.0312(10) Uani 1 1 d . . . . .
H24A H 0.8564 0.8146 1.2707 0.047 Uiso 1 1 calc GR . . . .
H24B H 1.0150 0.8022 1.3069 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.9289 0.7210 1.2609 0.047 Uiso 1 1 calc GR . . . .
C23A C 1.2015(5) 0.7937(2) 0.9134(2) 0.0358(10) Uani 1 1 d . . . . .
H23A H 1.2882 0.7687 0.9360 0.054 Uiso 1 1 calc GR . . . .
H23B H 1.2205 0.8125 0.8618 0.054 Uiso 1 1 calc GR . . . .
H23C H 1.1230 0.7490 0.9093 0.054 Uiso 1 1 calc GR . . . .
C6A C 0.5728(3) 0.3873(2) 1.0223(2) 0.0216(9) Uani 1 1 d . . . . .
H6A H 0.5519 0.3438 0.9812 0.026 Uiso 1 1 calc R . . . .
C4A C 0.7455(3) 0.4614(2) 0.9394(2) 0.0210(9) Uani 1 1 d . . . . .
C5A C 0.6708(3) 0.4558(2) 1.0127(2) 0.0189(8) Uani 1 1 d . . . . .
C1A C 0.7945(3) 0.5938(2) 1.0611(2) 0.0182(8) Uani 1 1 d . . . . .
C10A C 0.6967(3) 0.5196(2) 1.0738(2) 0.0160(8) Uani 1 1 d . . . . .
C3A C 0.8494(3) 0.5326(2) 0.9322(2) 0.0196(8) Uani 1 1 d . . . . .
C2A C 0.8685(3) 0.5978(2) 0.9890(2) 0.0168(8) Uani 1 1 d . . . . .
C7A C 0.5058(4) 0.3819(2) 1.0906(2) 0.0252(9) Uani 1 1 d . . . . .
H7A H 0.4390 0.3346 1.0962 0.030 Uiso 1 1 calc R . . . .
C9A C 0.6296(4) 0.5135(2) 1.1421(2) 0.0240(9) Uani 1 1 d . . . . .
H9A H 0.6489 0.5570 1.1834 0.029 Uiso 1 1 calc R . . . .
C11A C 0.9354(4) 0.5362(2) 0.8613(2) 0.0286(9) Uani 1 1 d . . . . .
H11A H 0.9354 0.4765 0.8350 0.034 Uiso 1 1 calc R . . . .
H11B H 1.0361 0.5538 0.8773 0.034 Uiso 1 1 calc R . . . .
C8A C 0.5341(4) 0.4439(2) 1.1508(2) 0.0278(9) Uani 1 1 d . . . . .
H8A H 0.4883 0.4390 1.1981 0.033 Uiso 1 1 calc R . . . .
C12A C 0.8794(4) 0.5992(3) 0.8045(2) 0.0373(11) Uani 1 1 d D . . . .
H12A H 0.8657 0.6574 0.8315 0.045 Uiso 0.837(5) 1 calc R . P A 1
H12B H 0.7854 0.5769 0.7808 0.045 Uiso 0.837(5) 1 calc R . P A 1
H12C H 0.8793 0.6568 0.8345 0.045 Uiso 0.163(5) 1 calc R . P A 2
H12D H 0.7770 0.5811 0.7940 0.045 Uiso 0.163(5) 1 calc R . P A 2
C5B C 0.8221(3) -0.0076(2) 0.5362(2) 0.0200(8) Uani 1 1 d . . . . .
C1B C 0.6772(3) -0.0468(2) 0.4173(2) 0.0199(8) Uani 1 1 d . . . . .
C4B C 0.7599(4) 0.0815(2) 0.5400(2) 0.0245(9) Uani 1 1 d . . . . .
C3B C 0.6501(4) 0.0998(2) 0.4816(2) 0.0234(9) Uani 1 1 d . . . . .
C2B C 0.6117(3) 0.0393(2) 0.4228(2) 0.0214(8) Uani 1 1 d . . . . .
C10B C 0.7781(3) -0.0711(2) 0.4789(2) 0.0205(8) Uani 1 1 d . . . . .
C15B C 0.3411(3) 0.0144(2) 0.2136(2) 0.0182(8) Uani 1 1 d . . . . .
C20B C 0.2986(3) -0.0531(2) 0.2608(2) 0.0197(8) Uani 1 1 d . . . . .
H20B H 0.2269 -0.0418 0.2969 0.024 Uiso 1 1 calc R . . . .
C18B C 0.4649(3) -0.1564(2) 0.2013(2) 0.0212(8) Uani 1 1 d . . . . .
C21B C 0.2857(3) 0.1059(2) 0.2288(2) 0.0227(9) Uani 1 1 d . . . . .
H21B H 0.2672 0.1140 0.2850 0.027 Uiso 1 1 calc R . . . .
C16B C 0.4437(3) -0.0060(2) 0.1595(2) 0.0199(8) Uani 1 1 d . . . . .
H16B H 0.4737 0.0379 0.1266 0.024 Uiso 1 1 calc R . . . .
C17B C 0.5036(3) -0.0899(2) 0.1525(2) 0.0206(8) Uani 1 1 d . . . . .
H17B H 0.5711 -0.1018 0.1142 0.025 Uiso 1 1 calc R . . . .
C24B C 0.5355(4) -0.2424(2) 0.1993(2) 0.0265(9) Uani 1 1 d . . . . .
H24D H 0.6221 -0.2388 0.1697 0.040 Uiso 1 1 calc GR . . . .
H24E H 0.4691 -0.2882 0.1748 0.040 Uiso 1 1 calc GR . . . .
H24F H 0.5620 -0.2569 0.2522 0.040 Uiso 1 1 calc GR . . . .
C23B C 0.3912(4) 0.1787(2) 0.2097(2) 0.0308(10) Uani 1 1 d . . . . .
H23D H 0.4840 0.1715 0.2372 0.046 Uiso 1 1 calc GR . . . .
H23E H 0.3537 0.2361 0.2259 0.046 Uiso 1 1 calc GR . . . .
H23F H 0.4038 0.1756 0.1539 0.046 Uiso 1 1 calc GR . . . .
C19B C 0.3591(3) -0.1362(2) 0.2560(2) 0.0213(8) Uani 1 1 d . . . . .
H19B H 0.3294 -0.1796 0.2894 0.026 Uiso 1 1 calc R . . . .
C22B C 0.1420(4) 0.1110(2) 0.1829(2) 0.0306(10) Uani 1 1 d . . . . .
H22D H 0.1575 0.1035 0.1275 0.046 Uiso 1 1 calc GR . . . .
H22E H 0.1009 0.1684 0.1946 0.046 Uiso 1 1 calc GR . . . .
H22F H 0.0756 0.0643 0.1973 0.046 Uiso 1 1 calc GR . . . .
C6B C 0.9265(3) -0.0275(3) 0.5923(2) 0.0235(9) Uani 1 1 d . . . . .
H6B H 0.9587 0.0158 0.6317 0.028 Uiso 1 1 calc R . . . .
C9B C 0.8352(4) -0.1547(2) 0.4763(2) 0.0249(9) Uani 1 1 d . . . . .
H9B H 0.8057 -0.1977 0.4360 0.030 Uiso 1 1 calc R . . . .
C7B C 0.9829(4) -0.1105(3) 0.5902(2) 0.0259(9) Uani 1 1 d . . . . .
H7B H 1.0545 -0.1240 0.6280 0.031 Uiso 1 1 calc R . . . .
C8B C 0.9349(4) -0.1738(3) 0.5331(2) 0.0279(9) Uani 1 1 d . . . . .
H8B H 0.9715 -0.2313 0.5333 0.034 Uiso 1 1 calc R . . . .
C11B C 0.5832(4) 0.1888(3) 0.4834(2) 0.0311(10) Uani 1 1 d . . . . .
H11C H 0.5962 0.2177 0.5362 0.037 Uiso 1 1 calc R . . . .
H11D H 0.4788 0.1813 0.4703 0.037 Uiso 1 1 calc R . . . .
C13A C 0.9881(7) 0.6083(5) 0.7417(3) 0.0583(14) Uani 0.837(5) 1 d D . P A 1
H13A H 1.0804 0.6330 0.7657 0.070 Uiso 0.837(5) 1 calc R . P A 1
H13B H 1.0057 0.5492 0.7174 0.070 Uiso 0.837(5) 1 calc R . P A 1
C13B C 0.5688(7) 0.3287(4) 0.4101(4) 0.0583(14) Uani 0.837(5) 1 d D . P A 1
H13E H 0.4687 0.3108 0.3928 0.070 Uiso 0.837(5) 1 calc R . P A 1
H13F H 0.5656 0.3664 0.4586 0.070 Uiso 0.837(5) 1 calc R . P A 1
C14B C 0.6341(9) 0.3803(5) 0.3503(4) 0.093(2) Uani 0.837(5) 1 d D . P A 1
H14G H 0.6550 0.3407 0.3058 0.140 Uiso 0.837(5) 1 calc GR . P A 1
H14H H 0.7235 0.4099 0.3718 0.140 Uiso 0.837(5) 1 calc GR . P A 1
H14I H 0.5669 0.4245 0.3338 0.140 Uiso 0.837(5) 1 calc GR . P A 1
C12B C 0.6522(4) 0.2470(3) 0.4259(3) 0.0447(12) Uani 1 1 d D . . . .
H12E H 0.7504 0.2655 0.4462 0.054 Uiso 0.837(5) 1 calc R . P A 1
H12F H 0.6611 0.2118 0.3765 0.054 Uiso 0.837(5) 1 calc R . P A 1
H12G H 0.6286 0.2255 0.3716 0.054 Uiso 0.163(5) 1 calc R . P A 2
H12H H 0.7577 0.2537 0.4351 0.054 Uiso 0.163(5) 1 calc R . P A 2
C13C C 0.934(4) 0.621(3) 0.7256(12) 0.0583(14) Uani 0.163(5) 1 d D . P A 2
H13C H 0.8680 0.6619 0.7014 0.070 Uiso 0.163(5) 1 calc R . P A 2
H13D H 0.9327 0.5659 0.6915 0.070 Uiso 0.163(5) 1 calc R . P A 2
C14A C 0.9358(9) 0.6671(5) 0.6800(4) 0.093(2) Uani 0.837(5) 1 d D . P A 1
H14A H 1.0090 0.6723 0.6417 0.140 Uiso 0.837(5) 1 calc GR . P A 1
H14B H 0.9179 0.7256 0.7039 0.140 Uiso 0.837(5) 1 calc GR . P A 1
H14C H 0.8465 0.6416 0.6545 0.140 Uiso 0.837(5) 1 calc GR . P A 1
C13D C 0.576(3) 0.3321(15) 0.4484(18) 0.0583(14) Uani 0.163(5) 1 d D . P A 2
H13G H 0.5567 0.3339 0.5041 0.070 Uiso 0.163(5) 1 calc R . P A 2
H13H H 0.6392 0.3834 0.4397 0.070 Uiso 0.163(5) 1 calc R . P A 2
C14D C 0.436(4) 0.338(3) 0.402(2) 0.093(2) Uani 0.163(5) 1 d D . P A 2
H14J H 0.4409 0.3042 0.3525 0.140 Uiso 0.163(5) 1 calc GR . P A 2
H14K H 0.4194 0.3999 0.3932 0.140 Uiso 0.163(5) 1 calc GR . P A 2
H14L H 0.3574 0.3142 0.4309 0.140 Uiso 0.163(5) 1 calc GR . P A 2
C14C C 1.090(5) 0.663(3) 0.733(2) 0.093(2) Uani 0.163(5) 1 d . . P A 2
H14D H 1.1601 0.6164 0.7356 0.140 Uiso 0.163(5) 1 calc GR . P A 2
H14E H 1.1015 0.7024 0.7799 0.140 Uiso 0.163(5) 1 calc GR . P A 2
H14F H 1.1070 0.6966 0.6877 0.140 Uiso 0.163(5) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1A Cl1A 2.3942(9) . ?
Ru1A O2A 2.056(2) . ?
Ru1A O1A 2.127(2) . ?
Ru1A C15A 2.168(3) . ?
Ru1A C20A 2.136(3) . ?
Ru1A C18A 2.172(3) . ?
Ru1A C16A 2.149(3) . ?
Ru1A C19A 2.158(3) . ?
Ru1A C17A 2.178(4) . ?
Ru1B Cl1B 2.3905(9) . ?
Ru1B O2B 2.056(2) . ?
Ru1B O1B 2.123(2) . ?
Ru1B C15B 2.153(3) . ?
Ru1B C20B 2.146(3) . ?
Ru1B C18B 2.191(3) . ?
Ru1B C16B 2.141(3) . ?
Ru1B C17B 2.174(3) . ?
Ru1B C19B 2.160(3) . ?
O2B C2B 1.306(4) . ?
O1B C1B 1.245(4) . ?
O3B C4B 1.232(4) . ?
O2A C2A 1.305(4) . ?
O1A C1A 1.253(4) . ?
O3A C4A 1.239(4) . ?
C15A C20A 1.427(5) . ?
C15A C21A 1.505(5) . ?
C15A C16A 1.415(5) . ?
C20A C19A 1.401(5) . ?
C21A C22A 1.537(4) . ?
C21A C23A 1.511(5) . ?
C18A C19A 1.420(5) . ?
C18A C17A 1.399(5) . ?
C18A C24A 1.495(5) . ?
C16A C17A 1.408(5) . ?
C6A C5A 1.387(5) . ?
C6A C7A 1.372(5) . ?
C4A C5A 1.486(5) . ?
C4A C3A 1.445(4) . ?
C5A C10A 1.397(5) . ?
C1A C10A 1.464(4) . ?
C1A C2A 1.462(5) . ?
C10A C9A 1.375(5) . ?
C3A C2A 1.355(5) . ?
C3A C11A 1.504(5) . ?
C7A C8A 1.372(5) . ?
C9A C8A 1.383(5) . ?
C11A C12A 1.506(5) . ?
C12A C13A 1.534(6) . ?
C12A C13C 1.534(9) . ?
C5B C4B 1.491(5) . ?
C5B C10B 1.380(5) . ?
C5B C6B 1.398(5) . ?
C1B C2B 1.464(5) . ?
C1B C10B 1.463(5) . ?
C4B C3B 1.451(5) . ?
C3B C2B 1.356(5) . ?
C3B C11B 1.510(5) . ?
C10B C9B 1.395(5) . ?
C15B C20B 1.415(5) . ?
C15B C21B 1.512(5) . ?
C15B C16B 1.400(5) . ?
C20B C19B 1.401(5) . ?
C18B C17B 1.411(5) . ?
C18B C24B 1.484(5) . ?
C18B C19B 1.428(5) . ?
C21B C23B 1.522(5) . ?
C21B C22B 1.532(4) . ?
C16B C17B 1.412(5) . ?
C6B C7B 1.383(5) . ?
C9B C8B 1.374(5) . ?
C7B C8B 1.385(5) . ?
C11B C12B 1.527(5) . ?
C13A C14A 1.513(7) . ?
C13B C14B 1.484(7) . ?
C13B C12B 1.521(6) . ?
C12B C13D 1.536(9) . ?
C13C C14C 1.57(5) . ?
C13D C14D 1.502(11) . ?

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
_geom_angle_publ_flag
O2A Ru1A Cl1A 86.25(7) . . ?
O2A Ru1A O1A 76.54(9) . . ?
O2A Ru1A C15A 98.65(11) . . ?
O2A Ru1A C20A 90.10(11) . . ?
O2A Ru1A C18A 145.40(12) . . ?
O2A Ru1A C16A 130.61(12) . . ?
O2A Ru1A C19A 109.70(11) . . ?
O2A Ru1A C17A 167.85(12) . . ?
O1A Ru1A Cl1A 84.03(6) . . ?
O1A Ru1A C15A 163.51(11) . . ?
O1A Ru1A C20A 124.91(11) . . ?
O1A Ru1A C18A 92.42(11) . . ?
O1A Ru1A C16A 152.05(12) . . ?
O1A Ru1A C19A 96.97(11) . . ?
O1A Ru1A C17A 115.41(12) . . ?
C15A Ru1A Cl1A 111.63(9) . . ?
C15A Ru1A C18A 82.67(13) . . ?
C15A Ru1A C17A 69.27(13) . . ?
C20A Ru1A Cl1A 149.04(10) . . ?
C20A Ru1A C15A 38.71(12) . . ?
C20A Ru1A C18A 69.31(13) . . ?
C20A Ru1A C16A 68.76(12) . . ?
C20A Ru1A C19A 38.07(13) . . ?
C20A Ru1A C17A 81.16(13) . . ?
C18A Ru1A Cl1A 125.66(10) . . ?
C18A Ru1A C17A 37.51(13) . . ?
C16A Ru1A Cl1A 90.64(9) . . ?
C16A Ru1A C15A 38.26(12) . . ?
C16A Ru1A C18A 68.58(14) . . ?
C16A Ru1A C19A 80.91(13) . . ?
C16A Ru1A C17A 37.96(13) . . ?
C19A Ru1A Cl1A 163.86(10) . . ?
C19A Ru1A C15A 69.50(13) . . ?
C19A Ru1A C18A 38.30(13) . . ?
C19A Ru1A C17A 68.06(13) . . ?
C17A Ru1A Cl1A 96.88(10) . . ?
O2B Ru1B Cl1B 84.92(7) . . ?
O2B Ru1B O1B 76.56(9) . . ?
O2B Ru1B C15B 93.52(11) . . ?
O2B Ru1B C20B 91.94(11) . . ?
O2B Ru1B C18B 153.45(11) . . ?
O2B Ru1B C16B 122.05(12) . . ?
O2B Ru1B C17B 160.22(12) . . ?
O2B Ru1B C19B 116.00(12) . . ?
O1B Ru1B Cl1B 84.25(6) . . ?
O1B Ru1B C15B 155.82(12) . . ?
O1B Ru1B C20B 118.83(11) . . ?
O1B Ru1B C18B 96.00(11) . . ?
O1B Ru1B C16B 160.94(12) . . ?
O1B Ru1B C17B 123.11(11) . . ?
O1B Ru1B C19B 94.65(11) . . ?
C15B Ru1B Cl1B 117.22(9) . . ?
C15B Ru1B C18B 83.03(13) . . ?
C15B Ru1B C17B 69.17(13) . . ?
C15B Ru1B C19B 69.64(13) . . ?
C20B Ru1B Cl1B 155.35(10) . . ?
C20B Ru1B C15B 38.45(12) . . ?
C20B Ru1B C18B 69.07(13) . . ?
C20B Ru1B C17B 80.44(13) . . ?
C20B Ru1B C19B 37.98(12) . . ?
C18B Ru1B Cl1B 120.10(9) . . ?
C16B Ru1B Cl1B 92.87(9) . . ?
C16B Ru1B C15B 38.05(13) . . ?
C16B Ru1B C20B 68.16(13) . . ?
C16B Ru1B C18B 69.15(13) . . ?
C16B Ru1B C17B 38.18(13) . . ?
C16B Ru1B C19B 81.10(13) . . ?
C17B Ru1B Cl1B 94.41(9) . . ?
C17B Ru1B C18B 37.71(13) . . ?
C19B Ru1B Cl1B 158.29(10) . . ?
C19B Ru1B C18B 38.32(13) . . ?
C19B Ru1B C17B 68.01(13) . . ?
C2B O2B Ru1B 114.5(2) . . ?
C1B O1B Ru1B 112.7(2) . . ?
C2A O2A Ru1A 115.5(2) . . ?
C1A O1A Ru1A 113.5(2) . . ?
C20A C15A Ru1A 69.44(18) . . ?
C20A C15A C21A 123.6(3) . . ?
C21A C15A Ru1A 128.6(2) . . ?
C16A C15A Ru1A 70.11(18) . . ?
C16A C15A C20A 116.7(3) . . ?
C16A C15A C21A 119.5(3) . . ?
C15A C20A Ru1A 71.85(18) . . ?
C19A C20A Ru1A 71.78(18) . . ?
C19A C20A C15A 121.4(3) . . ?
C15A C21A C22A 109.2(3) . . ?
C15A C21A C23A 114.9(3) . . ?
C23A C21A C22A 111.0(3) . . ?
C19A C18A Ru1A 70.3(2) . . ?
C19A C18A C24A 120.2(3) . . ?
C17A C18A Ru1A 71.5(2) . . ?
C17A C18A C19A 118.8(3) . . ?
C17A C18A C24A 120.9(3) . . ?
C24A C18A Ru1A 127.5(2) . . ?
C15A C16A Ru1A 71.62(18) . . ?
C17A C16A Ru1A 72.2(2) . . ?
C17A C16A C15A 122.1(3) . . ?
C20A C19A Ru1A 70.15(18) . . ?
C20A C19A C18A 120.6(3) . . ?
C18A C19A Ru1A 71.39(19) . . ?
C18A C17A Ru1A 71.0(2) . . ?
C18A C17A C16A 120.3(3) . . ?
C16A C17A Ru1A 69.9(2) . . ?
C7A C6A C5A 120.6(3) . . ?
O3A C4A C5A 118.9(3) . . ?
O3A C4A C3A 121.7(3) . . ?
C3A C4A C5A 119.4(3) . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A C10A 118.2(3) . . ?
C10A C5A C4A 120.9(3) . . ?
O1A C1A C10A 121.2(3) . . ?
O1A C1A C2A 117.8(3) . . ?
C2A C1A C10A 121.0(3) . . ?
C5A C10A C1A 117.4(3) . . ?
C9A C10A C5A 120.9(3) . . ?
C9A C10A C1A 121.7(3) . . ?
C4A C3A C11A 120.7(3) . . ?
C2A C3A C4A 120.1(3) . . ?
C2A C3A C11A 119.2(3) . . ?
O2A C2A C1A 114.5(3) . . ?
O2A C2A C3A 124.5(3) . . ?
C3A C2A C1A 120.9(3) . . ?
C8A C7A C6A 120.8(3) . . ?
C10A C9A C8A 119.9(3) . . ?
C3A C11A C12A 113.7(3) . . ?
C7A C8A C9A 119.6(4) . . ?
C11A C12A C13A 108.8(4) . . ?
C11A C12A C13C 129.9(15) . . ?
C10B C5B C4B 121.5(3) . . ?
C10B C5B C6B 119.2(3) . . ?
C6B C5B C4B 119.4(3) . . ?
O1B C1B C2B 118.2(3) . . ?
O1B C1B C10B 121.9(3) . . ?
C10B C1B C2B 119.8(3) . . ?
O3B C4B C5B 119.9(3) . . ?
O3B C4B C3B 122.1(3) . . ?
C3B C4B C5B 118.0(3) . . ?
C4B C3B C11B 119.9(3) . . ?
C2B C3B C4B 120.8(3) . . ?
C2B C3B C11B 119.2(3) . . ?
O2B C2B C1B 114.2(3) . . ?
O2B C2B C3B 124.7(3) . . ?
C3B C2B C1B 121.1(3) . . ?
C5B C10B C1B 118.3(3) . . ?
C5B C10B C9B 121.2(3) . . ?
C9B C10B C1B 120.3(3) . . ?
C20B C15B Ru1B 70.49(18) . . ?
C20B C15B C21B 119.1(3) . . ?
C21B C15B Ru1B 124.8(2) . . ?
C16B C15B Ru1B 70.52(19) . . ?
C16B C15B C20B 117.1(3) . . ?
C16B C15B C21B 123.5(3) . . ?
C15B C20B Ru1B 71.06(18) . . ?
C19B C20B Ru1B 71.57(19) . . ?
C19B C20B C15B 122.0(3) . . ?
C17B C18B Ru1B 70.5(2) . . ?
C17B C18B C24B 122.0(3) . . ?
C17B C18B C19B 117.2(3) . . ?
C24B C18B Ru1B 128.3(2) . . ?
C19B C18B Ru1B 69.68(19) . . ?
C19B C18B C24B 120.7(3) . . ?
C15B C21B C23B 113.4(3) . . ?
C15B C21B C22B 108.1(3) . . ?
C23B C21B C22B 111.3(3) . . ?
C15B C16B Ru1B 71.42(19) . . ?
C15B C16B C17B 121.8(3) . . ?
C17B C16B Ru1B 72.2(2) . . ?
C18B C17B Ru1B 71.8(2) . . ?
C18B C17B C16B 121.2(3) . . ?
C16B C17B Ru1B 69.6(2) . . ?
C20B C19B Ru1B 70.45(19) . . ?
C20B C19B C18B 120.7(3) . . ?
C18B C19B Ru1B 72.00(19) . . ?
C7B C6B C5B 119.8(3) . . ?
C8B C9B C10B 118.7(3) . . ?
C6B C7B C8B 120.0(3) . . ?
C9B C8B C7B 121.0(4) . . ?
C3B C11B C12B 110.7(3) . . ?
C14A C13A C12A 112.0(5) . . ?
C14B C13B C12B 112.2(5) . . ?
C11B C12B C13D 97.6(15) . . ?
C13B C12B C11B 113.9(4) . . ?
C12A C13C C14C 112(2) . . ?
C14D C13D C12B 112(2) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1A O2A C2A C1A -12.7(3) . . . . ?
Ru1A O2A C2A C3A 170.6(3) . . . . ?
Ru1A O1A C1A C10A -171.6(2) . . . . ?
Ru1A O1A C1A C2A 8.7(4) . . . . ?
Ru1A C15A C20A C19A -54.2(3) . . . . ?
Ru1A C15A C21A C22A 175.4(2) . . . . ?
Ru1A C15A C21A C23A -59.1(4) . . . . ?
Ru1A C15A C16A C17A 53.9(3) . . . . ?
Ru1A C20A C19A C18A -52.6(3) . . . . ?
Ru1A C18A C19A C20A 52.0(3) . . . . ?
Ru1A C18A C17A C16A -51.5(3) . . . . ?
Ru1A C16A C17A C18A 52.0(3) . . . . ?
Ru1B O2B C2B C1B -16.7(4) . . . . ?
Ru1B O2B C2B C3B 162.3(3) . . . . ?
Ru1B O1B C1B C2B 11.7(4) . . . . ?
Ru1B O1B C1B C10B -169.0(2) . . . . ?
Ru1B C15B C20B C19B -52.6(3) . . . . ?
Ru1B C15B C21B C23B 62.6(4) . . . . ?
Ru1B C15B C21B C22B -173.5(2) . . . . ?
Ru1B C15B C16B C17B 54.0(3) . . . . ?
Ru1B C20B C19B C18B -53.7(3) . . . . ?
Ru1B C18B C17B C16B -51.2(3) . . . . ?
Ru1B C18B C19B C20B 53.0(3) . . . . ?
Ru1B C16B C17B C18B 52.1(3) . . . . ?
O1B C1B C2B O2B 2.9(5) . . . . ?
O1B C1B C2B C3B -176.1(3) . . . . ?
O1B C1B C10B C5B 172.9(3) . . . . ?
O1B C1B C10B C9B -2.8(5) . . . . ?
O3B C4B C3B C2B 175.0(3) . . . . ?
O3B C4B C3B C11B -1.6(5) . . . . ?
O1A C1A C10A C5A 176.7(3) . . . . ?
O1A C1A C10A C9A -1.7(5) . . . . ?
O1A C1A C2A O2A 2.3(4) . . . . ?
O1A C1A C2A C3A 179.2(3) . . . . ?
O3A C4A C5A C6A 1.5(5) . . . . ?
O3A C4A C5A C10A -178.2(3) . . . . ?
O3A C4A C3A C2A 173.9(3) . . . . ?
O3A C4A C3A C11A -4.9(5) . . . . ?
C15A C20A C19A Ru1A 54.2(3) . . . . ?
C15A C20A C19A C18A 1.6(5) . . . . ?
C15A C16A C17A Ru1A -53.6(3) . . . . ?
C15A C16A C17A C18A -1.6(5) . . . . ?
C20A C15A C21A C22A -95.1(4) . . . . ?
C20A C15A C21A C23A 30.5(4) . . . . ?
C20A C15A C16A Ru1A -53.1(3) . . . . ?
C20A C15A C16A C17A 0.8(5) . . . . ?
C21A C15A C20A Ru1A -123.5(3) . . . . ?
C21A C15A C20A C19A -177.6(3) . . . . ?
C21A C15A C16A Ru1A 123.9(3) . . . . ?
C21A C15A C16A C17A 177.8(3) . . . . ?
C16A C15A C20A Ru1A 53.4(3) . . . . ?
C16A C15A C20A C19A -0.7(4) . . . . ?
C16A C15A C21A C22A 88.1(4) . . . . ?
C16A C15A C21A C23A -146.3(3) . . . . ?
C19A C18A C17A Ru1A 53.9(3) . . . . ?
C19A C18A C17A C16A 2.4(5) . . . . ?
C17A C18A C19A Ru1A -54.5(3) . . . . ?
C17A C18A C19A C20A -2.4(5) . . . . ?
C24A C18A C19A Ru1A 122.6(3) . . . . ?
C24A C18A C19A C20A 174.7(3) . . . . ?
C24A C18A C17A Ru1A -123.2(3) . . . . ?
C24A C18A C17A C16A -174.6(3) . . . . ?
C6A C5A C10A C1A -176.8(3) . . . . ?
C6A C5A C10A C9A 1.6(5) . . . . ?
C6A C7A C8A C9A 1.0(5) . . . . ?
C4A C5A C10A C1A 2.9(4) . . . . ?
C4A C5A C10A C9A -178.7(3) . . . . ?
C4A C3A C2A O2A -178.1(3) . . . . ?
C4A C3A C2A C1A 5.4(5) . . . . ?
C4A C3A C11A C12A 100.7(4) . . . . ?
C5A C6A C7A C8A 0.0(5) . . . . ?
C5A C4A C3A C2A -6.1(5) . . . . ?
C5A C4A C3A C11A 175.1(3) . . . . ?
C5A C10A C9A C8A -0.6(5) . . . . ?
C1A C10A C9A C8A 177.7(3) . . . . ?
C10A C1A C2A O2A -177.4(3) . . . . ?
C10A C1A C2A C3A -0.6(5) . . . . ?
C10A C9A C8A C7A -0.7(5) . . . . ?
C3A C4A C5A C6A -178.5(3) . . . . ?
C3A C4A C5A C10A 1.8(5) . . . . ?
C3A C11A C12A C13A 171.1(4) . . . . ?
C3A C11A C12A C13C -179(2) . . . . ?
C2A C1A C10A C5A -3.6(4) . . . . ?
C2A C1A C10A C9A 178.0(3) . . . . ?
C2A C3A C11A C12A -78.1(4) . . . . ?
C7A C6A C5A C4A 179.0(3) . . . . ?
C7A C6A C5A C10A -1.3(5) . . . . ?
C11A C3A C2A O2A 0.7(5) . . . . ?
C11A C3A C2A C1A -175.8(3) . . . . ?
C11A C12A C13A C14A 177.1(5) . . . . ?
C11A C12A C13C C14C -63(4) . . . . ?
C5B C4B C3B C2B -3.8(5) . . . . ?
C5B C4B C3B C11B 179.5(3) . . . . ?
C5B C10B C9B C8B 1.3(5) . . . . ?
C5B C6B C7B C8B -0.6(5) . . . . ?
C1B C10B C9B C8B 176.9(3) . . . . ?
C4B C5B C10B C1B 5.3(5) . . . . ?
C4B C5B C10B C9B -179.1(3) . . . . ?
C4B C5B C6B C7B 178.7(3) . . . . ?
C4B C3B C2B O2B -177.6(3) . . . . ?
C4B C3B C2B C1B 1.3(5) . . . . ?
C4B C3B C11B C12B 99.3(4) . . . . ?
C3B C11B C12B C13B 166.2(4) . . . . ?
C3B C11B C12B C13D -173.9(12) . . . . ?
C2B C1B C10B C5B -7.8(5) . . . . ?
C2B C1B C10B C9B 176.5(3) . . . . ?
C2B C3B C11B C12B -77.4(4) . . . . ?
C10B C5B C4B O3B -178.5(3) . . . . ?
C10B C5B C4B C3B 0.4(5) . . . . ?
C10B C5B C6B C7B -0.8(5) . . . . ?
C10B C1B C2B O2B -176.4(3) . . . . ?
C10B C1B C2B C3B 4.6(5) . . . . ?
C10B C9B C8B C7B -2.7(5) . . . . ?
C15B C20B C19B Ru1B 52.3(3) . . . . ?
C15B C20B C19B C18B -1.4(5) . . . . ?
C15B C16B C17B Ru1B -53.7(3) . . . . ?
C15B C16B C17B C18B -1.5(5) . . . . ?
C20B C15B C21B C23B 148.1(3) . . . . ?
C20B C15B C21B C22B -88.0(4) . . . . ?
C20B C15B C16B Ru1B -54.6(2) . . . . ?
C20B C15B C16B C17B -0.6(4) . . . . ?
C21B C15B C20B Ru1B -119.7(3) . . . . ?
C21B C15B C20B C19B -172.2(3) . . . . ?
C21B C15B C16B Ru1B 119.4(3) . . . . ?
C21B C15B C16B C17B 173.4(3) . . . . ?
C16B C15B C20B Ru1B 54.6(2) . . . . ?
C16B C15B C20B C19B 2.1(5) . . . . ?
C16B C15B C21B C23B -25.8(5) . . . . ?
C16B C15B C21B C22B 98.1(4) . . . . ?
C17B C18B C19B Ru1B -53.8(3) . . . . ?
C17B C18B C19B C20B -0.8(4) . . . . ?
C24B C18B C17B Ru1B -123.6(3) . . . . ?
C24B C18B C17B C16B -174.8(3) . . . . ?
C24B C18B C19B Ru1B 123.2(3) . . . . ?
C24B C18B C19B C20B 176.2(3) . . . . ?
C19B C18B C17B Ru1B 53.4(3) . . . . ?
C19B C18B C17B C16B 2.2(4) . . . . ?
C6B C5B C4B O3B 2.0(5) . . . . ?
C6B C5B C4B C3B -179.1(3) . . . . ?
C6B C5B C10B C1B -175.2(3) . . . . ?
C6B C5B C10B C9B 0.4(5) . . . . ?
C6B C7B C8B C9B 2.4(6) . . . . ?
C11B C3B C2B O2B -0.9(6) . . . . ?
C11B C3B C2B C1B 178.0(3) . . . . ?
C11B C12B C13D C14D -90(3) . . . . ?
C13A C12A C13C C14C -37(3) . . . . ?
C13B C12B C13D C14D 43(3) . . . . ?
C14B C13B C12B C11B -176.3(5) . . . . ?
C14B C13B C12B C13D 131(4) . . . . ?
C13C C12A C13A C14A 18(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.553 0.500 0.500 392.4 121.8 ?

_exptl_crystal_recrystallization_method 'n-hexane/chloroform diffusion'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KuKi32_0m
_database_code_depnum_ccdc_archive 'CCDC 1469089'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 Cl O3 Ru'
_chemical_formula_sum            'C22 H23 Cl O3 Ru'
_chemical_formula_weight         471.92

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.5644(8)
_cell_length_b                   7.9491(4)
_cell_length_c                   15.7175(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.110(2)
_cell_angle_gamma                90
_cell_volume                     1914.42(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      3.215
_cell_measurement_theta_max      25.332

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.978
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22737
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         27.880
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4557
_reflns_number_gt                4242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0245P)²+1.3125P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4557
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75043(11) 1.0889(2) -0.00180(12) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.77645(11) 1.1803(2) -0.06684(11) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.71286(12) 1.2190(2) -0.14806(12) 0.0200(4) Uani 1 1 d . . . . .
H3A H 0.7307 1.3243 -0.1738 0.024 Uiso 1 1 calc R U . . .
H3B H 0.6542 1.2371 -0.1335 0.024 Uiso 1 1 calc R U . . .
C4 C 0.70846(17) 1.0773(3) -0.21384(15) 0.0356(5) Uani 1 1 d . . . . .
H4A H 0.7646 1.0683 -0.2337 0.053 Uiso 1 1 calc R U . . .
H4B H 0.6623 1.1013 -0.2632 0.053 Uiso 1 1 calc R U . . .
H4C H 0.6957 0.9711 -0.1870 0.053 Uiso 1 1 calc R U . . .
C5 C 0.86624(12) 1.2392(2) -0.05825(12) 0.0196(4) Uani 1 1 d . . . . .
C6 C 0.93131(11) 1.1893(2) 0.02020(12) 0.0183(4) Uani 1 1 d . . . . .
C7 C 0.90525(11) 1.0942(2) 0.08630(12) 0.0161(3) Uani 1 1 d . . . . .
C8 C 0.81301(12) 1.04941(19) 0.07796(12) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.96576(13) 1.0425(2) 0.15818(13) 0.0201(4) Uani 1 1 d . . . . .
H9 H 0.9476 0.9772 0.2024 0.024 Uiso 1 1 calc R U . . .
C10 C 1.05266(13) 1.0880(3) 0.16388(14) 0.0249(4) Uani 1 1 d . . . . .
H10 H 1.0944 1.0536 0.2123 0.030 Uiso 1 1 calc R U . . .
C11 C 1.07898(12) 1.1840(3) 0.09884(14) 0.0269(4) Uani 1 1 d . . . . .
H11 H 1.1386 1.2146 0.1032 0.032 Uiso 1 1 calc R U . . .
C12 C 1.01851(13) 1.2353(2) 0.02751(13) 0.0236(4) Uani 1 1 d . . . . .
H12 H 1.0368 1.3018 -0.0162 0.028 Uiso 1 1 calc R U . . .
C13 C 0.53644(11) 0.7905(2) 0.05922(12) 0.0188(4) Uani 1 1 d . . . . .
H13 H 0.5077 0.8133 -0.0017 0.023 Uiso 1 1 calc R U . . .
C14 C 0.51261(11) 0.8902(2) 0.12571(12) 0.0186(4) Uani 1 1 d . . . . .
H14 H 0.4678 0.9802 0.1098 0.022 Uiso 1 1 calc R U . . .
C15 C 0.56340(12) 0.8907(2) 0.21085(12) 0.0200(4) Uani 1 1 d . . . . .
C16 C 0.54162(14) 1.0051(3) 0.27985(14) 0.0271(4) Uani 1 1 d . . . . .
H16A H 0.5074 0.9433 0.3163 0.041 Uiso 1 1 calc R U . . .
H16B H 0.5076 1.1009 0.2530 0.041 Uiso 1 1 calc R U . . .
H16C H 0.5957 1.0460 0.3154 0.041 Uiso 1 1 calc R U . . .
C17 C 0.63821(12) 0.7867(2) 0.22618(12) 0.0204(4) Uani 1 1 d . . . . .
H17 H 0.6816 0.8032 0.2805 0.024 Uiso 1 1 calc R U . . .
C18 C 0.66220(12) 0.6865(2) 0.15916(13) 0.0203(4) Uani 1 1 d . . . . .
H18 H 0.7219 0.6360 0.1686 0.024 Uiso 1 1 calc R U . . .
C19 C 0.61253(12) 0.6852(2) 0.07369(13) 0.0194(4) Uani 1 1 d . . . . .
C20 C 0.64200(14) 0.5841(2) 0.00182(14) 0.0239(4) Uani 1 1 d . . . . .
H20 H 0.6272 0.4638 0.0109 0.029 Uiso 1 1 calc R U . . .
C21 C 0.74084(16) 0.5933(3) 0.00683(18) 0.0379(5) Uani 1 1 d . . . . .
H21A H 0.7590 0.7114 0.0069 0.057 Uiso 1 1 calc R U . . .
H21B H 0.7569 0.5357 -0.0432 0.057 Uiso 1 1 calc R U . . .
H21C H 0.7700 0.5387 0.0601 0.057 Uiso 1 1 calc R U . . .
C22 C 0.59489(17) 0.6333(3) -0.08807(15) 0.0386(6) Uani 1 1 d . . . . .
H22A H 0.5320 0.6163 -0.0918 0.058 Uiso 1 1 calc R U . . .
H22B H 0.6160 0.5633 -0.1314 0.058 Uiso 1 1 calc R U . . .
H22C H 0.6064 0.7519 -0.0988 0.058 Uiso 1 1 calc R U . . .
O1 O 0.67195(8) 1.02903(16) -0.00427(8) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.78452(8) 0.97559(15) 0.13719(8) 0.0166(3) Uani 1 1 d . . . . .
O3 O 0.89036(10) 1.3278(2) -0.11405(10) 0.0316(3) Uani 1 1 d . . . . .
Cl Cl 0.64597(3) 1.23774(5) 0.15126(3) 0.02111(10) Uani 1 1 d . . . . .
Ru Ru 0.64733(2) 0.94428(2) 0.11504(2) 0.01354(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.305(2) . ?
C1 C2 1.372(2) . ?
C1 C8 1.480(2) . ?
C2 C5 1.457(2) . ?
C2 C3 1.503(2) . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O3 1.233(2) . ?
C5 C6 1.505(3) . ?
C6 C12 1.391(3) . ?
C6 C7 1.401(3) . ?
C7 C9 1.399(3) . ?
C7 C8 1.462(2) . ?
C8 O2 1.246(2) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.412(3) . ?
C13 C19 1.435(3) . ?
C13 Ru 2.1706(17) . ?
C13 H13 1.0000 . ?
C14 C15 1.430(3) . ?
C14 Ru 2.1756(17) . ?
C14 H14 1.0000 . ?
C15 C17 1.414(3) . ?
C15 C16 1.499(3) . ?
C15 Ru 2.2014(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.422(3) . ?
C17 Ru 2.1744(17) . ?
C17 H17 1.0000 . ?
C18 C19 1.428(3) . ?
C18 Ru 2.1624(17) . ?
C18 H18 1.0000 . ?
C19 C20 1.521(3) . ?
C19 Ru 2.1984(18) . ?
C20 C22 1.524(3) . ?
C20 C21 1.528(3) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1 Ru 2.0904(13) . ?
O2 Ru 2.1169(13) . ?
Cl Ru 2.4022(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
_geom_angle_publ_flag
O1 C1 C2 124.61(16) . . ?
O1 C1 C8 114.91(15) . . ?
C2 C1 C8 120.47(16) . . ?
C1 C2 C5 120.31(16) . . ?
C1 C2 C3 120.31(16) . . ?
C5 C2 C3 119.38(16) . . ?
C2 C3 C4 111.69(16) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 C2 121.60(17) . . ?
O3 C5 C6 119.21(17) . . ?
C2 C5 C6 119.19(15) . . ?
C12 C6 C7 119.08(17) . . ?
C12 C6 C5 120.33(17) . . ?
C7 C6 C5 120.59(16) . . ?
C9 C7 C6 121.03(17) . . ?
C9 C7 C8 120.78(17) . . ?
C6 C7 C8 118.18(16) . . ?
O2 C8 C7 121.35(17) . . ?
O2 C8 C1 117.72(16) . . ?
C7 C8 C1 120.93(16) . . ?
C10 C9 C7 119.06(19) . . ?
C10 C9 H9 120.5 . . ?
C7 C9 H9 120.5 . . ?
C9 C10 C11 120.27(19) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.45(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C6 C12 C11 120.09(19) . . ?
C6 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C19 121.78(17) . . ?
C14 C13 Ru 71.23(10) . . ?
C19 C13 Ru 71.87(10) . . ?
C14 C13 H13 118.4 . . ?
C19 C13 H13 118.4 . . ?
Ru C13 H13 118.4 . . ?
C13 C14 C15 121.36(17) . . ?
C13 C14 Ru 70.85(10) . . ?
C15 C14 Ru 71.91(10) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
Ru C14 H14 118.6 . . ?
C17 C15 C14 117.47(18) . . ?
C17 C15 C16 121.04(18) . . ?
C14 C15 C16 121.38(17) . . ?
C17 C15 Ru 70.12(10) . . ?
C14 C15 Ru 69.96(10) . . ?
C16 C15 Ru 127.89(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.12(17) . . ?
C15 C17 Ru 72.19(10) . . ?
C18 C17 Ru 70.41(10) . . ?
C15 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
Ru C17 H17 118.7 . . ?
C17 C18 C19 122.15(17) . . ?
C17 C18 Ru 71.32(10) . . ?
C19 C18 Ru 72.26(9) . . ?
C17 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
Ru C18 H18 118.2 . . ?
C18 C19 C13 116.12(18) . . ?
C18 C19 C20 121.24(16) . . ?
C13 C19 C20 122.57(17) . . ?
C18 C19 Ru 69.53(10) . . ?
C13 C19 Ru 69.77(10) . . ?
C20 C19 Ru 128.59(13) . . ?
C19 C20 C22 113.22(17) . . ?
C19 C20 C21 111.62(17) . . ?
C22 C20 C21 110.6(2) . . ?
C19 C20 H20 107.0 . . ?
C22 C20 H20 107.0 . . ?
C21 C20 H20 107.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 O1 Ru 114.13(11) . . ?
C8 O2 Ru 114.43(11) . . ?
O1 Ru O2 76.77(5) . . ?
O1 Ru C18 124.53(6) . . ?
O2 Ru C18 90.60(6) . . ?
O1 Ru C13 94.41(6) . . ?
O2 Ru C13 147.16(6) . . ?
C18 Ru C13 68.21(7) . . ?
O1 Ru C17 162.65(6) . . ?
O2 Ru C17 98.15(6) . . ?
C18 Ru C17 38.27(7) . . ?
C13 Ru C17 80.84(7) . . ?
O1 Ru C14 117.63(6) . . ?
O2 Ru C14 165.59(6) . . ?
C18 Ru C14 80.70(7) . . ?
C13 Ru C14 37.92(7) . . ?
C17 Ru C14 67.94(7) . . ?
O1 Ru C19 96.38(6) . . ?
O2 Ru C19 110.35(6) . . ?
C18 Ru C19 38.21(7) . . ?
C13 Ru C19 38.35(7) . . ?
C17 Ru C19 69.54(7) . . ?
C14 Ru C19 69.32(7) . . ?
O1 Ru C15 154.20(6) . . ?
O2 Ru C15 127.79(6) . . ?
C18 Ru C15 68.92(7) . . ?
C13 Ru C15 69.04(7) . . ?
C17 Ru C15 37.69(7) . . ?
C14 Ru C15 38.13(7) . . ?
C19 Ru C15 82.88(7) . . ?
O1 Ru Cl 84.85(4) . . ?
O2 Ru Cl 84.12(4) . . ?
C18 Ru Cl 148.10(6) . . ?
C13 Ru Cl 127.10(5) . . ?
C17 Ru Cl 111.38(5) . . ?
C14 Ru Cl 97.18(5) . . ?
C19 Ru Cl 165.41(5) . . ?
C15 Ru Cl 89.70(5) . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.088

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_maku241_0m
_database_code_depnum_ccdc_archive 'CCDC 1469090'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Cl N O3 Ru'
_chemical_formula_sum            'C22 H24 Cl N O3 Ru'
_chemical_formula_weight         486.94

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.3763(6)
_cell_length_b                   9.2791(3)
_cell_length_c                   23.9785(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.607(2)
_cell_angle_gamma                90
_cell_volume                     4042.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      3.126
_cell_measurement_theta_max      25.698

_exptl_crystal_description       fragment
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.931
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22609
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         27.835
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4778
_reflns_number_gt                4180
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0254P)²+4.4241P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4778
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31925(10) 0.2016(2) 0.63959(8) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.39566(10) 0.1894(2) 0.63173(8) 0.0181(4) Uani 1 1 d . . . . .
C3 C 0.45634(11) 0.2302(2) 0.67228(9) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.4483 0.2620 0.7085 0.026 Uiso 1 1 calc R U . . .
C4 C 0.52729(11) 0.2241(2) 0.65941(9) 0.0231(4) Uani 1 1 d . . . . .
H4 H 0.5675 0.2512 0.6871 0.028 Uiso 1 1 calc R U . . .
C5 C 0.54034(11) 0.1789(2) 0.60652(9) 0.0248(4) Uani 1 1 d . . . . .
H5 H 0.5890 0.1782 0.5977 0.030 Uiso 1 1 calc R U . . .
C6 C 0.48218(10) 0.1349(2) 0.56684(9) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.4914 0.1023 0.5310 0.027 Uiso 1 1 calc R U . . .
C7 C 0.40984(10) 0.1377(2) 0.57880(8) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.34901(10) 0.0875(2) 0.53663(8) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.27695(10) 0.0956(2) 0.54432(8) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.21315(10) 0.0321(2) 0.50460(8) 0.0237(4) Uani 1 1 d . . . . .
H10A H 0.2289 0.0130 0.4676 0.028 Uiso 1 1 calc R U . . .
H10B H 0.1723 0.1026 0.4988 0.028 Uiso 1 1 calc R U . . .
C11 C 0.18588(13) -0.1081(3) 0.52780(11) 0.0370(6) Uani 1 1 d . . . . .
H11A H 0.2269 -0.1762 0.5356 0.056 Uiso 1 1 calc R U . . .
H11B H 0.1472 -0.1499 0.5000 0.056 Uiso 1 1 calc R U . . .
H11C H 0.1661 -0.0880 0.5628 0.056 Uiso 1 1 calc R U . . .
C12 C 0.26157(10) 0.1594(2) 0.59529(8) 0.0178(4) Uani 1 1 d . . . . .
C13 C 0.11853(11) 0.3959(2) 0.73301(9) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.1258 0.5025 0.7369 0.028 Uiso 1 1 calc R U . . .
C14 C 0.16749(11) 0.3037(2) 0.76702(8) 0.0216(4) Uani 1 1 d . . . . .
C15 C 0.22151(12) 0.3594(2) 0.81551(9) 0.0273(5) Uani 1 1 d . . . . .
H15A H 0.2365 0.4575 0.8071 0.041 Uiso 1 1 calc R U . . .
H15B H 0.2649 0.2967 0.8213 0.041 Uiso 1 1 calc R U . . .
H15C H 0.1984 0.3605 0.8498 0.041 Uiso 1 1 calc R U . . .
C16 C 0.16674(11) 0.1549(2) 0.75221(8) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.2077 0.0914 0.7701 0.025 Uiso 1 1 calc R U . . .
C17 C 0.11721(10) 0.1018(2) 0.70632(8) 0.0208(4) Uani 1 1 d . . . . .
H17 H 0.1244 0.0018 0.6926 0.025 Uiso 1 1 calc R U . . .
C18 C 0.06572(10) 0.1944(2) 0.67285(9) 0.0208(4) Uani 1 1 d . . . . .
C19 C 0.01547(10) 0.1313(2) 0.62256(9) 0.0250(5) Uani 1 1 d . . . . .
H19 H 0.0360 0.0354 0.6140 0.030 Uiso 1 1 calc R U . . .
C20 C -0.06080(11) 0.1054(3) 0.63902(11) 0.0354(6) Uani 1 1 d . . . . .
H20A H -0.0835 0.1981 0.6457 0.053 Uiso 1 1 calc R U . . .
H20B H -0.0560 0.0473 0.6735 0.053 Uiso 1 1 calc R U . . .
H20C H -0.0917 0.0543 0.6084 0.053 Uiso 1 1 calc R U . . .
C21 C 0.01108(13) 0.2235(3) 0.56965(10) 0.0381(6) Uani 1 1 d . . . . .
H21A H -0.0143 0.3140 0.5753 0.057 Uiso 1 1 calc R U . . .
H21B H -0.0162 0.1714 0.5376 0.057 Uiso 1 1 calc R U . . .
H21C H 0.0609 0.2445 0.5620 0.057 Uiso 1 1 calc R U . . .
C22 C 0.06681(10) 0.3415(2) 0.68689(9) 0.0224(4) Uani 1 1 d . . . . .
H22 H 0.0400 0.4113 0.6594 0.027 Uiso 1 1 calc R U . . .
N N 0.29244(9) 0.25008(18) 0.68580(7) 0.0194(4) Uani 1 1 d . . . . .
O1 O 0.19431(7) 0.17569(16) 0.60313(6) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.33454(8) 0.28636(16) 0.72999(6) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.37222(8) 0.03171(18) 0.49060(6) 0.0264(3) Uani 1 1 d . . . . .
Cl Cl 0.20999(2) 0.49704(5) 0.63160(2) 0.02035(11) Uani 1 1 d . . . . .
Ru Ru 0.18082(2) 0.27659(2) 0.67696(2) 0.01652(6) Uani 1 1 d . . . . .
H99 H 0.3415(14) 0.027(3) 0.4642(12) 0.042(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N 1.355(3) . ?
C1 C12 1.438(3) . ?
C1 C2 1.449(3) . ?
C2 C7 1.417(3) . ?
C2 C3 1.417(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.467(3) . ?
C8 O3 1.345(2) . ?
C8 C9 1.366(3) . ?
C9 C12 1.424(3) . ?
C9 C10 1.515(3) . ?
C10 C11 1.528(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O1 1.286(2) . ?
C13 C14 1.410(3) . ?
C13 C22 1.438(3) . ?
C13 Ru 2.192(2) . ?
C13 H13 1.0000 . ?
C14 C16 1.425(3) . ?
C14 C15 1.503(3) . ?
C14 Ru 2.2237(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.408(3) . ?
C16 Ru 2.177(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.432(3) . ?
C17 Ru 2.177(2) . ?
C17 H17 1.0000 . ?
C18 C22 1.405(3) . ?
C18 C19 1.522(3) . ?
C18 Ru 2.2367(19) . ?
C19 C21 1.522(3) . ?
C19 C20 1.531(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 Ru 2.2265(19) . ?
C22 H22 1.0000 . ?
N O2 1.261(2) . ?
N Ru 2.0452(16) . ?
O1 Ru 2.0503(14) . ?
O3 H99 0.78(3) . ?
Cl Ru 2.4144(5) . ?

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
_geom_angle_publ_flag
N C1 C12 112.11(16) . . ?
N C1 C2 127.62(17) . . ?
C12 C1 C2 120.26(17) . . ?
C7 C2 C3 118.29(17) . . ?
C7 C2 C1 117.06(16) . . ?
C3 C2 C1 124.61(18) . . ?
C4 C3 C2 120.42(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.81(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.73(19) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.87(19) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 119.80(17) . . ?
C6 C7 C8 120.08(18) . . ?
C2 C7 C8 120.12(17) . . ?
O3 C8 C9 124.39(17) . . ?
O3 C8 C7 112.68(16) . . ?
C9 C8 C7 122.92(18) . . ?
C8 C9 C12 117.37(17) . . ?
C8 C9 C10 124.63(18) . . ?
C12 C9 C10 117.84(16) . . ?
C9 C10 C11 111.56(17) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
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 C12 C9 119.51(16) . . ?
O1 C12 C1 118.57(17) . . ?
C9 C12 C1 121.88(17) . . ?
C14 C13 C22 121.52(19) . . ?
C14 C13 Ru 72.62(11) . . ?
C22 C13 Ru 72.33(11) . . ?
C14 C13 H13 118.8 . . ?
C22 C13 H13 118.8 . . ?
Ru C13 H13 118.8 . . ?
C13 C14 C16 117.55(18) . . ?
C13 C14 C15 121.93(19) . . ?
C16 C14 C15 120.45(18) . . ?
C13 C14 Ru 70.15(11) . . ?
C16 C14 Ru 69.33(11) . . ?
C15 C14 Ru 129.36(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 120.98(18) . . ?
C17 C16 Ru 71.14(11) . . ?
C14 C16 Ru 72.90(11) . . ?
C17 C16 H16 119.0 . . ?
C14 C16 H16 119.0 . . ?
Ru C16 H16 119.0 . . ?
C16 C17 C18 121.58(19) . . ?
C16 C17 Ru 71.12(11) . . ?
C18 C17 Ru 73.34(11) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
Ru C17 H17 118.7 . . ?
C22 C18 C17 117.64(18) . . ?
C22 C18 C19 123.30(18) . . ?
C17 C18 C19 118.99(19) . . ?
C22 C18 Ru 71.26(11) . . ?
C17 C18 Ru 68.82(11) . . ?
C19 C18 Ru 128.58(14) . . ?
C18 C19 C21 113.21(18) . . ?
C18 C19 C20 109.04(18) . . ?
C21 C19 C20 111.51(18) . . ?
C18 C19 H19 107.6 . . ?
C21 C19 H19 107.6 . . ?
C20 C19 H19 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 C13 120.65(18) . . ?
C18 C22 Ru 72.05(11) . . ?
C13 C22 Ru 69.70(11) . . ?
C18 C22 H22 118.9 . . ?
C13 C22 H22 118.9 . . ?
Ru C22 H22 118.9 . . ?
O2 N C1 121.57(16) . . ?
O2 N Ru 122.33(13) . . ?
C1 N Ru 115.90(12) . . ?
C12 O1 Ru 115.00(12) . . ?
C8 O3 H99 114(2) . . ?
N Ru O1 77.62(6) . . ?
N Ru C16 95.36(7) . . ?
O1 Ru C16 121.58(7) . . ?
N Ru C17 117.11(7) . . ?
O1 Ru C17 94.55(7) . . ?
C16 Ru C17 37.74(7) . . ?
N Ru C13 127.23(7) . . ?
O1 Ru C13 154.43(7) . . ?
C16 Ru C13 67.41(8) . . ?
C17 Ru C13 79.80(8) . . ?
N Ru C14 99.64(7) . . ?
O1 Ru C14 159.27(7) . . ?
C16 Ru C14 37.77(8) . . ?
C17 Ru C14 68.13(8) . . ?
C13 Ru C14 37.23(7) . . ?
N Ru C22 165.15(7) . . ?
O1 Ru C22 116.94(6) . . ?
C16 Ru C22 79.70(8) . . ?
C17 Ru C22 66.89(8) . . ?
C13 Ru C22 37.97(8) . . ?
C14 Ru C22 67.88(7) . . ?
N Ru C18 152.97(7) . . ?
O1 Ru C18 92.41(6) . . ?
C16 Ru C18 68.33(7) . . ?
C17 Ru C18 37.84(7) . . ?
C13 Ru C18 67.79(8) . . ?
C14 Ru C18 80.82(7) . . ?
C22 Ru C18 36.69(8) . . ?
N Ru Cl 82.05(5) . . ?
O1 Ru Cl 86.23(4) . . ?
C16 Ru Cl 151.04(6) . . ?
C17 Ru Cl 160.58(5) . . ?
C13 Ru Cl 91.14(6) . . ?
C14 Ru Cl 113.95(6) . . ?
C22 Ru Cl 95.45(6) . . ?
C18 Ru Cl 122.77(5) . . ?

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.074

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_maku238
_database_code_depnum_ccdc_archive 'CCDC 1469091'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.25


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8478(4)
_cell_length_b                   6.9261(2)
_cell_length_c                   13.7030(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.488(2)
_cell_angle_gamma                90
_cell_volume                     1112.14(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4208
_cell_measurement_theta_min      3.112
_cell_measurement_theta_max      25.212

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9970
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11807
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2184
_reflns_number_gt                1492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          
;
 Refined as mixture of 74% E and 26% Z isomeres.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0493P)²+0.2872P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2184
_refine_ls_number_parameters     169
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.48286(17) 0.2586(3) 0.48892(14) 0.0193(5) Uani 1 1 d D . . . .
C1' C 0.80362(17) 0.1189(3) 0.54348(15) 0.0251(5) Uani 1 1 d . . . . .
H1'1 H 0.8075 0.0831 0.4741 0.030 Uiso 1 1 calc R U . . .
H1'2 H 0.8309 0.0075 0.5857 0.030 Uiso 1 1 calc R U . . .
C2 C 0.60251(17) 0.2151(3) 0.47844(14) 0.0200(5) Uani 1 1 d D . . . .
C2' C 0.88151(17) 0.2923(3) 0.57197(16) 0.0275(5) Uani 1 1 d . . . . .
H2'1 H 0.8582 0.3996 0.5256 0.033 Uiso 1 1 calc R U . . .
H2'2 H 0.8713 0.3359 0.6389 0.033 Uiso 1 1 calc R U . . .
C3' C 1.00734(18) 0.2480(3) 0.57075(17) 0.0345(6) Uani 1 1 d . . . . .
H3'1 H 1.0319 0.1452 0.6183 0.052 Uiso 1 1 calc R U . . .
H3'2 H 1.0527 0.3644 0.5886 0.052 Uiso 1 1 calc R U . . .
H3'3 H 1.0183 0.2060 0.5045 0.052 Uiso 1 1 calc R U . . .
C3 C 0.68198(17) 0.1622(3) 0.55478(14) 0.0208(5) Uani 1 1 d . . . . .
C4 C 0.65065(17) 0.1536(3) 0.65298(14) 0.0217(5) Uani 1 1 d . . . . .
C5 C 0.50428(19) 0.1964(3) 0.76360(14) 0.0258(5) Uani 1 1 d . . . . .
H5 H 0.5611 0.1641 0.8175 0.031 Uiso 1 1 calc R U . . .
C5A C 0.53257(17) 0.2020(3) 0.66820(14) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.39493(19) 0.2373(3) 0.78058(16) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.3764 0.2323 0.8457 0.036 Uiso 1 1 calc R U . . .
C7 C 0.31247(19) 0.2856(3) 0.70202(15) 0.0292(5) Uani 1 1 d . . . . .
H7 H 0.2371 0.3140 0.7136 0.035 Uiso 1 1 calc R U . . .
C8 C 0.33821(18) 0.2931(3) 0.60681(15) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.2805 0.3264 0.5537 0.029 Uiso 1 1 calc R U . . .
C8A C 0.44894(17) 0.2520(3) 0.58824(14) 0.0201(5) Uani 1 1 d . . . . .
N1 N 0.4241(4) 0.2941(13) 0.4038(2) 0.0244(10) Uani 0.740(2) 1 d D . P A 1
O1 O 0.31215(17) 0.3334(3) 0.40412(13) 0.0271(5) Uani 0.740(2) 1 d D . P A 1
H1 H 0.2805 0.3550 0.3462 0.041 Uiso 0.740(2) 1 calc R U P A 1
O2 O 0.6298(12) 0.2354(17) 0.3863(5) 0.0250(15) Uani 0.740(2) 1 d D . P A 1
H2 H 0.5708 0.2626 0.3467 0.038 Uiso 0.740(2) 1 calc R U P A 1
N1A N 0.4026(14) 0.309(4) 0.4187(7) 0.0244(10) Uani 0.260(2) 1 d D . P A 2
O1A O 0.4240(5) 0.3198(8) 0.3241(4) 0.0271(5) Uani 0.260(2) 1 d D . P A 2
H1A H 0.4838 0.2580 0.3188 0.041 Uiso 0.260(2) 1 calc R U P A 2
O2A O 0.637(4) 0.204(6) 0.3882(15) 0.0250(15) Uani 0.260(2) 1 d D . P A 2
H2A H 0.7027 0.2510 0.3913 0.038 Uiso 0.260(2) 1 calc R U P A 2
O3 O 0.72203(12) 0.1033(2) 0.72400(10) 0.0322(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.291(3) . ?
C1 N1A 1.298(8) . ?
C1 C8A 1.476(3) . ?
C1 C2 1.477(3) . ?
C1' C3 1.502(3) . ?
C1' C2' 1.529(3) . ?
C1' H1'1 0.9900 . ?
C1' H1'2 0.9900 . ?
C2 C3 1.351(3) . ?
C2 O2 1.356(4) . ?
C2 O2A 1.359(8) . ?
C2' C3' 1.524(3) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' H3'1 0.9800 . ?
C3' H3'2 0.9800 . ?
C3' H3'3 0.9800 . ?
C3 C4 1.449(3) . ?
C4 O3 1.241(2) . ?
C4 C5A 1.483(3) . ?
C5 C6 1.379(3) . ?
C5 C5A 1.397(3) . ?
C5 H5 0.9500 . ?
C5A C8A 1.408(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.402(3) . ?
C8 H8 0.9500 . ?
N1 O1 1.354(5) . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?
N1A O1A 1.360(11) . ?
O1A H1A 0.8400 . ?
O2A H2A 0.8400 . ?

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
_geom_angle_publ_flag
N1 C1 C8A 130.9(3) . . ?
N1A C1 C8A 115.0(7) . . ?
N1 C1 C2 110.4(3) . . ?
N1A C1 C2 126.3(7) . . ?
C8A C1 C2 118.64(17) . . ?
C3 C1' C2' 111.67(16) . . ?
C3 C1' H1'1 109.3 . . ?
C2' C1' H1'1 109.3 . . ?
C3 C1' H1'2 109.3 . . ?
C2' C1' H1'2 109.3 . . ?
H1'1 C1' H1'2 107.9 . . ?
C3 C2 O2 121.0(6) . . ?
C3 C2 O2A 115.0(18) . . ?
C3 C2 C1 123.33(18) . . ?
O2 C2 C1 115.7(6) . . ?
O2A C2 C1 121.3(18) . . ?
C3' C2' C1' 113.18(17) . . ?
C3' C2' H2'1 108.9 . . ?
C1' C2' H2'1 108.9 . . ?
C3' C2' H2'2 108.9 . . ?
C1' C2' H2'2 108.9 . . ?
H2'1 C2' H2'2 107.8 . . ?
C2' C3' H3'1 109.5 . . ?
C2' C3' H3'2 109.5 . . ?
H3'1 C3' H3'2 109.5 . . ?
C2' C3' H3'3 109.5 . . ?
H3'1 C3' H3'3 109.5 . . ?
H3'2 C3' H3'3 109.5 . . ?
C2 C3 C4 119.05(18) . . ?
C2 C3 C1' 122.96(18) . . ?
C4 C3 C1' 117.95(17) . . ?
O3 C4 C3 120.09(19) . . ?
O3 C4 C5A 120.05(18) . . ?
C3 C4 C5A 119.84(17) . . ?
C6 C5 C5A 120.89(19) . . ?
C6 C5 H5 119.6 . . ?
C5A C5 H5 119.6 . . ?
C5 C5A C8A 119.76(19) . . ?
C5 C5A C4 119.15(17) . . ?
C8A C5A C4 121.09(17) . . ?
C5 C6 C7 119.43(19) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C8A 120.38(19) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
C8 C8A C5A 118.60(18) . . ?
C8 C8A C1 123.40(18) . . ?
C5A C8A C1 117.99(18) . . ?
C1 N1 O1 115.6(3) . . ?
N1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
C1 N1A O1A 120.1(12) . . ?
N1A O1A H1A 109.5 . . ?
C2 O2A H2A 109.5 . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-2

