# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cu113



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

'Chlorido(η⁶-p-isopropyltoluene)(5-chloro-7-iodoquinolin-8-olato)ruthenium(II)'

;

_chemical_name_common            
Chlorido(η⁶-p-cymene)(clioquinolato)ruthenium(II)

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            
'C19 H18 Cl2 I N O Ru'

_chemical_formula_weight         575.21



loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source














C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/n'

_symmetry_space_group_name_Hall  '-P 2yn'



loop_

_symmetry_equiv_pos_as_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                   15.2671(2)

_cell_length_b                   8.0205(2)

_cell_length_c                   15.8597(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 100.0050(10)

_cell_angle_gamma                90.00

_cell_volume                     1912.48(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    7387

_cell_measurement_theta_min      3.6700

_cell_measurement_theta_max      74.4790



_exptl_crystal_description       plaque

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.998

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    21.935

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.0584

_exptl_absorpt_correction_T_max  0.0966

_exptl_absorpt_process_details   
;

CrysAlisPro, Agilent Technologies,

Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)

(compiled Feb  1 2013,16:14:44)

Empirical absorption correction using spherical harmonics,

implemented in SCALE3 ABSPACK scaling algorithm.

;



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      150(2)

_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           'Cu K\a'

_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'

_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            15988

_diffrn_reflns_av_R_equivalents  0.0574

_diffrn_reflns_av_sigmaI/netI    0.0379

_diffrn_reflns_limit_h_min       -17

_diffrn_reflns_limit_h_max       19

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -19

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         3.71

_diffrn_reflns_theta_max         74.74

_reflns_number_total             3889

_reflns_number_gt                3549

_reflns_threshold_expression     >2σ(I)



_computing_data_collection       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)

(compiled Feb  1 2013,16:14:44)

;

_computing_cell_refinement       
;

CrysAlisPro, Agilent Technologies,

Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)

(compiled Feb  1 2013,16:14:44)

;

_computing_data_reduction        
;

CrysAlisPro, Agilent Technologies,

Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)

(compiled Feb  1 2013,16:14:44)

;

_computing_structure_solution    'SIR92 (Altomare et al., 1993)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    ?

_computing_publication_material  ?





_refine_special_details          
;

Refinement of F² against ALL reflections.  The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement.  R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0824P)²+0.9099P] 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         3889

_refine_ls_number_parameters     229

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0453

_refine_ls_R_factor_gt           0.0418

_refine_ls_wR_factor_ref         0.1183

_refine_ls_wR_factor_gt          0.1132

_refine_ls_goodness_of_fit_ref   1.032

_refine_ls_restrained_S_all      1.032

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group











































Ru1 Ru 0.334059(16) 0.05434(4) 0.412416(17) 0.03078(12) Uani 1 1 d . . .
I7 I 0.32101(2) -0.17233(5) 0.72382(2) 0.06142(15) Uani 1 1 d . . .
Cl1 Cl 0.34784(6) -0.23818(13) 0.37767(6) 0.0404(2) Uani 1 1 d . . .
Cl5 Cl -0.02984(9) -0.30695(17) 0.54799(11) 0.0623(4) Uani 1 1 d . . .
C4 C 0.0257(3) -0.1225(7) 0.3933(3) 0.0465(10) Uani 1 1 d . . .
H4 H -0.0330 -0.1638 0.3903 0.056 Uiso 1 1 calc R . .
C12 C 0.4065(3) 0.1259(6) 0.3094(3) 0.0454(10) Uani 1 1 d . . .
C6 C 0.1390(3) -0.2269(6) 0.6160(3) 0.0470(10) Uani 1 1 d . . .
H6 H 0.1266 -0.2756 0.6672 0.056 Uiso 1 1 calc R . .
N1 N 0.1977(2) -0.0037(5) 0.3979(2) 0.0354(7) Uani 1 1 d . . .
O8 O 0.32371(19) -0.0302(4) 0.53398(18) 0.0387(6) Uani 1 1 d . . .
C5 C 0.0736(3) -0.2217(6) 0.5445(3) 0.0448(10) Uani 1 1 d . . .
C8 C 0.2459(3) -0.0891(5) 0.5407(3) 0.0341(8) Uani 1 1 d . . .
C10 C 0.0894(3) -0.1426(5) 0.4687(3) 0.0391(9) Uani 1 1 d . . .
C7 C 0.2240(3) -0.1611(6) 0.6141(3) 0.0421(9) Uani 1 1 d . . .
C18 C 0.3509(4) 0.4013(9) 0.5334(4) 0.0671(16) Uani 1 1 d . . .
H18 H 0.3687 0.5189 0.5242 0.081 Uiso 1 1 calc R . .
C14 C 0.3120(3) 0.3151(6) 0.3776(3) 0.0459(10) Uani 1 1 d . . .
H14 H 0.2596 0.3807 0.3728 0.055 Uiso 1 1 calc R . .
C16 C 0.4501(3) 0.2111(6) 0.4594(3) 0.0393(8) Uani 1 1 d . . .
H16 H 0.4921 0.2069 0.5111 0.047 Uiso 1 1 calc R . .
C9 C 0.1755(3) -0.0801(5) 0.4680(3) 0.0327(7) Uani 1 1 d . . .
C2 C 0.1367(3) 0.0155(6) 0.3285(3) 0.0407(9) Uani 1 1 d . . .
H2 H 0.1520 0.0702 0.2799 0.049 Uiso 1 1 calc R . .
C3 C 0.0498(3) -0.0437(6) 0.3255(3) 0.0489(11) Uani 1 1 d . . .
H3 H 0.0071 -0.0281 0.2750 0.059 Uiso 1 1 calc R . .
C15 C 0.3709(3) 0.3088(6) 0.4568(3) 0.0414(9) Uani 1 1 d . . .
C17 C 0.4675(3) 0.1215(6) 0.3882(3) 0.0418(9) Uani 1 1 d . . .
H17 H 0.5203 0.0573 0.3926 0.050 Uiso 1 1 calc R . .
C13 C 0.3295(3) 0.2253(6) 0.3048(3) 0.0469(10) Uani 1 1 d . . .
H13 H 0.2886 0.2324 0.2524 0.056 Uiso 1 1 calc R . .
C20 C 0.4022(7) 0.3561(15) 0.6159(5) 0.107(3) Uani 1 1 d . . .
H20A H 0.3971 0.2359 0.6250 0.161 Uiso 1 1 calc R . .
H20B H 0.3795 0.4167 0.6612 0.161 Uiso 1 1 calc R . .
H20C H 0.4648 0.3852 0.6174 0.161 Uiso 1 1 calc R . .
C19 C 0.2526(4) 0.4114(9) 0.5362(5) 0.0712(17) Uani 1 1 d . . .
H19A H 0.2269 0.2992 0.5312 0.107 Uiso 1 1 calc R . .
H19B H 0.2232 0.4806 0.4887 0.107 Uiso 1 1 calc R . .
H19C H 0.2441 0.4612 0.5906 0.107 Uiso 1 1 calc R . .
C11 C 0.4222(5) 0.0234(9) 0.2345(4) 0.0671(17) Uani 1 1 d . . .
H11A H 0.3700 0.0303 0.1889 0.101 Uiso 1 1 calc R . .
H11B H 0.4322 -0.0930 0.2524 0.101 Uiso 1 1 calc R . .
H11C H 0.4745 0.0657 0.2133 0.101 Uiso 1 1 calc R . .






_geom_special_details            
;

All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix.  The cell s.u.'s are taken

into account individually in the estimation of s.u.'s in distances, angles

and torsion angles; correlations between s.u.'s in cell parameters are only

used when they are defined by crystal symmetry.  An approximate (isotropic)

treatment of cell s.u.'s is used for estimating s.u.'s 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

































Ru1 O8 2.076(3) . ?
Ru1 N1 2.106(3) . ?
Ru1 C14 2.174(4) . ?
Ru1 C13 2.181(4) . ?
Ru1 C16 2.194(4) . ?
Ru1 C15 2.200(4) . ?
Ru1 C12 2.203(4) . ?
Ru1 C17 2.204(4) . ?
Ru1 Cl1 2.4275(10) . ?
I7 C7 2.081(5) . ?
Cl5 C5 1.730(4) . ?
C4 C3 1.353(8) . ?
C4 C10 1.412(7) . ?
C12 C13 1.413(7) . ?
C12 C17 1.423(7) . ?
C12 C11 1.497(7) . ?
C6 C5 1.375(8) . ?
C6 C7 1.406(6) . ?
N1 C2 1.322(6) . ?
N1 C9 1.362(5) . ?
O8 C8 1.300(5) . ?
C5 C10 1.416(7) . ?
C8 C7 1.392(6) . ?
C8 C9 1.435(6) . ?
C10 C9 1.410(5) . ?
C18 C20 1.450(11) . ?
C18 C15 1.499(7) . ?
C18 C19 1.511(8) . ?
C14 C15 1.412(7) . ?
C14 C13 1.425(8) . ?
C16 C17 1.402(7) . ?
C16 C15 1.436(6) . ?
C2 C3 1.403(7) . ?



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






















































































O8 Ru1 N1 78.22(12) . . ?
O8 Ru1 C14 121.12(17) . . ?
N1 Ru1 C14 94.51(16) . . ?
O8 Ru1 C13 159.24(18) . . ?
N1 Ru1 C13 99.02(16) . . ?
C14 Ru1 C13 38.2(2) . . ?
O8 Ru1 C16 93.36(14) . . ?
N1 Ru1 C16 152.61(16) . . ?
C14 Ru1 C16 67.38(17) . . ?
C13 Ru1 C16 79.64(17) . . ?
O8 Ru1 C15 93.58(15) . . ?
N1 Ru1 C15 115.63(15) . . ?
C14 Ru1 C15 37.66(18) . . ?
C13 Ru1 C15 68.82(19) . . ?
C16 Ru1 C15 38.15(16) . . ?
O8 Ru1 C12 154.60(16) . . ?
N1 Ru1 C12 126.23(16) . . ?
C14 Ru1 C12 68.7(2) . . ?
C13 Ru1 C12 37.6(2) . . ?
C16 Ru1 C12 67.85(17) . . ?
C15 Ru1 C12 82.07(18) . . ?
O8 Ru1 C17 117.61(15) . . ?
N1 Ru1 C17 163.89(16) . . ?
C14 Ru1 C17 80.06(18) . . ?
C13 Ru1 C17 67.36(18) . . ?
C16 Ru1 C17 37.18(17) . . ?
C15 Ru1 C17 68.68(17) . . ?
C12 Ru1 C17 37.69(18) . . ?
O8 Ru1 Cl1 85.33(9) . . ?
N1 Ru1 Cl1 83.37(10) . . ?
C14 Ru1 Cl1 152.59(15) . . ?
C13 Ru1 Cl1 114.98(15) . . ?
C16 Ru1 Cl1 122.28(12) . . ?
C15 Ru1 Cl1 160.38(12) . . ?
C12 Ru1 Cl1 90.52(14) . . ?
C17 Ru1 Cl1 94.45(13) . . ?
C3 C4 C10 119.0(4) . . ?
C13 C12 C17 118.1(4) . . ?
C13 C12 C11 121.0(5) . . ?
C17 C12 C11 120.9(5) . . ?
C13 C12 Ru1 70.4(3) . . ?
C17 C12 Ru1 71.2(2) . . ?
C11 C12 Ru1 127.9(4) . . ?
C5 C6 C7 120.8(4) . . ?
C2 N1 C9 119.5(4) . . ?
C2 N1 Ru1 127.2(3) . . ?
C9 N1 Ru1 113.1(3) . . ?
C8 O8 Ru1 114.4(2) . . ?
C6 C5 C10 120.4(4) . . ?
C6 C5 Cl5 119.9(4) . . ?
C10 C5 Cl5 119.7(4) . . ?
O8 C8 C7 125.1(4) . . ?
O8 C8 C9 118.9(3) . . ?
C7 C8 C9 116.0(4) . . ?
C9 C10 C4 117.3(4) . . ?
C9 C10 C5 117.6(4) . . ?
C4 C10 C5 125.2(4) . . ?
C8 C7 C6 122.0(4) . . ?
C8 C7 I7 118.5(3) . . ?
C6 C7 I7 119.4(4) . . ?
C20 C18 C15 117.0(6) . . ?
C20 C18 C19 111.7(7) . . ?
C15 C18 C19 113.2(5) . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 Ru1 72.2(3) . . ?
C13 C14 Ru1 71.2(3) . . ?
C17 C16 C15 122.2(4) . . ?
C17 C16 Ru1 71.8(2) . . ?
C15 C16 Ru1 71.1(2) . . ?
N1 C9 C10 122.1(4) . . ?
N1 C9 C8 114.9(3) . . ?
C10 C9 C8 123.0(4) . . ?
N1 C2 C3 120.9(5) . . ?
C4 C3 C2 121.2(4) . . ?
C14 C15 C16 116.6(4) . . ?
C14 C15 C18 121.0(5) . . ?
C16 C15 C18 122.4(4) . . ?
C14 C15 Ru1 70.2(3) . . ?
C16 C15 Ru1 70.7(2) . . ?
C18 C15 Ru1 129.9(4) . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 Ru1 71.1(2) . . ?
C12 C17 Ru1 71.1(2) . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 Ru1 72.1(2) . . ?
C14 C13 Ru1 70.6(3) . . ?



_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        74.74

_diffrn_measured_fraction_theta_full 0.995

_refine_diff_density_max         1.365

_refine_diff_density_min         -1.185

_refine_diff_density_rms         0.149



_database_code_depnum_ccdc_archive 'CCDC 977981'
