# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_CA1510101
_audit_block_doi                 10.5517/cc13qckr
_database_code_depnum_ccdc_archive 'CCDC 1034394'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 Cl2 N2 O8 Ru2'
_chemical_formula_weight         833.71

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.895(11)
_cell_length_b                   11.081(12)
_cell_length_c                   32.12(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3522(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4588
_cell_measurement_theta_min      1.94
_cell_measurement_theta_max      21.71

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.057
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            7489
_diffrn_reflns_av_unetI/netI     0.0898
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         21.710
_diffrn_reflns_theta_full        21.710
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4135
_reflns_number_gt                3084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_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 AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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 > 2sigma(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. 
 The restraints of ISOR was adapted on isopropyl and O atoms. 
 The ISOR was also adapted on C13 and C14.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²] 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_abs_structure_details 
;
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4135
_refine_ls_number_parameters     397
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002

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
Ru2 Ru 0.34574(13) 0.70266(15) 0.08809(5) 0.0388(5) Uani 1 1 d . . . . .
Cl2 Cl 0.1180(5) 0.7360(6) 0.06463(18) 0.0676(19) Uani 1 1 d . . . . .
O5 O 0.2587(14) 0.5546(10) 0.1194(4) 0.044(4) Uani 1 1 d . . . . .
O6 O 0.1080(16) 0.5055(13) 0.1662(5) 0.072(5) Uani 1 1 d . . . . .
O7 O 0.068(2) 0.9844(18) 0.2745(6) 0.105(6) Uani 1 1 d . U . . .
H7B H 0.0124 0.9916 0.2933 0.157 Uiso 0.5 1 calc R U P . .
O8 O 0.008(3) 0.797(3) 0.2849(9) 0.194(12) Uani 1 1 d . U . . .
H8B H -0.0397 0.8312 0.3021 0.291 Uiso 0.5 1 calc R U P . .
N2 N 0.2705(15) 0.7829(16) 0.1428(5) 0.046(4) Uani 1 1 d . . . . .
H2A H 0.3332 0.8316 0.1534 0.055 Uiso 1 1 calc R U . . .
H2B H 0.1985 0.8275 0.1366 0.055 Uiso 1 1 calc R U . . .
C16 C 0.353(2) 0.884(3) 0.0048(8) 0.102(11) Uani 1 1 d . . . . .
H16A H 0.3203 0.8375 -0.0184 0.153 Uiso 1 1 calc R U . . .
H16B H 0.2780 0.9219 0.0186 0.153 Uiso 1 1 calc R U . . .
H16C H 0.4140 0.9449 -0.0051 0.153 Uiso 1 1 calc R U . . .
C17 C 0.426(2) 0.802(3) 0.0350(7) 0.063(6) Uani 1 1 d . . . . .
C18 C 0.485(2) 0.840(2) 0.0715(9) 0.072(8) Uani 1 1 d . . . . .
H18A H 0.4649 0.9227 0.0808 0.086 Uiso 1 1 calc R U . . .
C19 C 0.549(2) 0.763(3) 0.0996(8) 0.070(8) Uani 1 1 d . . . . .
H19A H 0.5747 0.7930 0.1272 0.084 Uiso 1 1 calc R U . . .
C20 C 0.550(2) 0.636(2) 0.0910(9) 0.064(7) Uani 1 1 d . . . . .
C21 C 0.489(2) 0.591(2) 0.0533(7) 0.052(6) Uani 1 1 d . . . . .
H21A H 0.4732 0.5044 0.0494 0.062 Uiso 1 1 calc R U . . .
C22 C 0.4319(19) 0.675(2) 0.0268(7) 0.060(7) Uani 1 1 d . . . . .
H22A H 0.3710 0.6443 0.0052 0.072 Uiso 1 1 calc R U . . .
C23 C 0.608(3) 0.548(3) 0.1192(10) 0.114(10) Uani 1 1 d . U . . .
H23A H 0.5463 0.4793 0.1145 0.137 Uiso 1 1 calc R U . . .
C24 C 0.608(6) 0.551(5) 0.1608(17) 0.27(3) Uani 1 1 d . U . . .
H24A H 0.6532 0.4809 0.1714 0.410 Uiso 1 1 calc R U . . .
H24B H 0.6546 0.6223 0.1699 0.410 Uiso 1 1 calc R U . . .
H24C H 0.5167 0.5527 0.1708 0.410 Uiso 1 1 calc R U . . .
C25 C 0.748(5) 0.492(5) 0.1010(18) 0.26(3) Uani 1 1 d . U . . .
H25A H 0.7444 0.4906 0.0711 0.383 Uiso 1 1 calc R U . . .
H25B H 0.8225 0.5412 0.1098 0.383 Uiso 1 1 calc R U . . .
H25C H 0.7599 0.4113 0.1112 0.383 Uiso 1 1 calc R U . . .
C26 C 0.233(2) 0.6939(19) 0.1739(5) 0.049(5) Uani 1 1 d . . . . .
H26A H 0.3156 0.6765 0.1896 0.058 Uiso 1 1 calc R U . . .
C27 C 0.129(2) 0.7359(18) 0.2061(6) 0.066(7) Uani 1 1 d . . . . .
H27A H 0.0444 0.7526 0.1919 0.080 Uiso 1 1 calc R U . . .
H27B H 0.1126 0.6707 0.2256 0.080 Uiso 1 1 calc R U . . .
C28 C 0.171(2) 0.847(2) 0.2301(7) 0.078(8) Uani 1 1 d . . . . .
H28A H 0.1671 0.9155 0.2115 0.094 Uiso 1 1 calc R U . . .
H28B H 0.2639 0.8367 0.2387 0.094 Uiso 1 1 calc R U . . .
C29 C 0.088(3) 0.875(3) 0.2675(10) 0.097(9) Uani 1 1 d . U . . .
C30 C 0.196(2) 0.5765(17) 0.1516(6) 0.042(5) Uani 1 1 d . . . . .
Ru1 Ru 0.18866(13) 0.20174(15) 0.08793(5) 0.0387(5) Uani 1 1 d . . . . .
Cl1 Cl 0.4165(5) 0.2326(6) 0.0641(2) 0.077(2) Uani 1 1 d . . . . .
O1 O 0.2670(13) 0.0555(11) 0.1205(6) 0.055(5) Uani 1 1 d . . . . .
O2 O 0.4276(15) 0.0004(12) 0.1657(5) 0.074(5) Uani 1 1 d . . . . .
O3 O 0.485(2) 0.289(3) 0.2752(8) 0.153(9) Uani 1 1 d . U . . .
O4 O 0.4022(17) 0.4703(15) 0.2763(5) 0.084(5) Uani 1 1 d . U . . .
H4B H 0.4598 0.4786 0.2944 0.126 Uiso 1 1 calc R U . . .
N1 N 0.2646(16) 0.2838(16) 0.1431(5) 0.054(5) Uani 1 1 d . . . . .
H1A H 0.3057 0.3523 0.1361 0.065 Uiso 1 1 calc R U . . .
H1E H 0.1950 0.3027 0.1594 0.065 Uiso 1 1 calc R U . . .
C1 C 0.181(2) 0.394(3) 0.0064(8) 0.097(11) Uani 1 1 d . . . . .
H1B H 0.2159 0.3540 -0.0179 0.146 Uiso 1 1 calc R U . . .
H1C H 0.1194 0.4565 -0.0021 0.146 Uiso 1 1 calc R U . . .
H1D H 0.2539 0.4289 0.0219 0.146 Uiso 1 1 calc R U . . .
C2 C 0.1044(19) 0.301(2) 0.0342(8) 0.064(6) Uani 1 1 d . . . . .
C3 C 0.1048(19) 0.173(2) 0.0251(6) 0.055(6) Uani 1 1 d . . . . .
H3A H 0.1604 0.1404 0.0025 0.066 Uiso 1 1 calc R U . . .
C4 C 0.041(2) 0.097(2) 0.0544(8) 0.064(7) Uani 1 1 d . . . . .
H4A H 0.0585 0.0104 0.0519 0.077 Uiso 1 1 calc R U . . .
C5 C -0.018(2) 0.136(3) 0.0907(10) 0.073(7) Uani 1 1 d . . . . .
C6 C -0.016(2) 0.258(3) 0.0979(7) 0.065(8) Uani 1 1 d . . . . .
H6A H -0.0415 0.2861 0.1258 0.078 Uiso 1 1 calc R U . . .
C7 C 0.046(2) 0.341(2) 0.0706(8) 0.057(7) Uani 1 1 d . . . . .
H7A H 0.0617 0.4241 0.0797 0.069 Uiso 1 1 calc R U . . .
C8 C -0.072(4) 0.014(4) 0.1215(12) 0.146(13) Uani 1 1 d . U . . .
H8A H -0.0251 -0.0635 0.1176 0.175 Uiso 1 1 calc R U . . .
C9 C -0.227(4) 0.021(4) 0.1062(13) 0.159(16) Uani 1 1 d . U . . .
H9A H -0.2338 -0.0069 0.0780 0.238 Uiso 1 1 calc R U . . .
H9B H -0.2827 -0.0283 0.1238 0.238 Uiso 1 1 calc R U . . .
H9C H -0.2579 0.1033 0.1077 0.238 Uiso 1 1 calc R U . . .
C10 C -0.082(4) 0.054(4) 0.1590(12) 0.187(17) Uani 1 1 d . U . . .
H10A H 0.0053 0.0540 0.1719 0.281 Uiso 1 1 calc R U . . .
H10B H -0.1174 0.1345 0.1584 0.281 Uiso 1 1 calc R U . . .
H10C H -0.1422 0.0029 0.1746 0.281 Uiso 1 1 calc R U . . .
C11 C 0.358(2) 0.079(2) 0.1499(8) 0.056(7) Uani 1 1 d . . . . .
C12 C 0.361(2) 0.209(2) 0.1675(8) 0.076(8) Uani 1 1 d . . . . .
H12A H 0.4523 0.2418 0.1645 0.091 Uiso 1 1 calc R U . . .
C13 C 0.323(3) 0.208(4) 0.2121(11) 0.141(13) Uani 1 1 d . U . . .
H13A H 0.2576 0.1435 0.2146 0.169 Uiso 1 1 calc R U . . .
H13B H 0.4033 0.1805 0.2265 0.169 Uiso 1 1 calc R U . . .
C14 C 0.269(4) 0.307(4) 0.2390(12) 0.159(14) Uani 1 1 d . U . . .
H14A H 0.2095 0.2754 0.2605 0.191 Uiso 1 1 calc R U . . .
H14B H 0.2208 0.3670 0.2228 0.191 Uiso 1 1 calc R U . . .
C15 C 0.414(3) 0.362(3) 0.2592(8) 0.080(8) Uani 1 1 d . U . . .


_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
Ru2 O5 2.108(12) . ?
Ru2 N2 2.106(15) . ?
Ru2 C18 2.12(2) . ?
Ru2 C19 2.16(2) . ?
Ru2 C20 2.15(2) . ?
Ru2 C22 2.17(2) . ?
Ru2 C17 2.18(2) . ?
Ru2 C21 2.190(19) . ?
Ru2 Cl2 2.405(6) . ?
O5 C30 1.23(2) . ?
O6 C30 1.26(2) . ?
O7 C29 1.25(3) . ?
O8 C29 1.30(4) . ?
N2 C26 1.45(3) . ?
C16 C17 1.52(3) . ?
C17 C18 1.38(3) . ?
C17 C22 1.43(4) . ?
C18 C19 1.39(3) . ?
C19 C20 1.44(3) . ?
C20 C23 1.45(4) . ?
C20 C21 1.44(3) . ?
C21 C22 1.39(3) . ?
C23 C24 1.34(5) . ?
C23 C25 1.63(5) . ?
C26 C27 1.53(3) . ?
C26 C30 1.53(3) . ?
C27 C28 1.51(3) . ?
C28 C29 1.49(3) . ?
Ru1 O1 2.080(14) . ?
Ru1 N1 2.128(16) . ?
Ru1 C6 2.15(2) . ?
Ru1 C4 2.15(2) . ?
Ru1 C7 2.16(2) . ?
Ru1 C5 2.18(2) . ?
Ru1 C3 2.21(2) . ?
Ru1 C2 2.21(2) . ?
Ru1 Cl1 2.405(6) . ?
O1 C11 1.33(3) . ?
O2 C11 1.22(2) . ?
O3 C15 1.18(3) . ?
O4 C15 1.32(3) . ?
N1 C12 1.49(2) . ?
C1 C2 1.56(3) . ?
C2 C7 1.38(3) . ?
C2 C3 1.44(4) . ?
C3 C4 1.42(3) . ?
C4 C5 1.37(4) . ?
C5 C6 1.37(3) . ?
C5 C8 1.76(4) . ?
C6 C7 1.42(3) . ?
C8 C10 1.29(4) . ?
C8 C9 1.62(5) . ?
C11 C12 1.55(3) . ?
C12 C13 1.48(4) . ?
C13 C14 1.49(5) . ?
C14 C15 1.70(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
O5 Ru2 N2 77.6(6) . . ?
O5 Ru2 C18 160.7(10) . . ?
N2 Ru2 C18 97.8(8) . . ?
O5 Ru2 C19 122.9(9) . . ?
N2 Ru2 C19 93.2(8) . . ?
C18 Ru2 C19 38.1(9) . . ?
O5 Ru2 C20 95.4(7) . . ?
N2 Ru2 C20 116.1(9) . . ?
C18 Ru2 C20 69.6(10) . . ?
C19 Ru2 C20 39.1(8) . . ?
O5 Ru2 C22 119.0(8) . . ?
N2 Ru2 C22 163.1(9) . . ?
C18 Ru2 C22 67.5(9) . . ?
C19 Ru2 C22 80.3(8) . . ?
C20 Ru2 C22 67.8(9) . . ?
O5 Ru2 C17 156.2(9) . . ?
N2 Ru2 C17 124.7(9) . . ?
C18 Ru2 C17 37.3(9) . . ?
C19 Ru2 C17 68.6(9) . . ?
C20 Ru2 C17 82.3(9) . . ?
C22 Ru2 C17 38.4(10) . . ?
O5 Ru2 C21 93.9(7) . . ?
N2 Ru2 C21 153.3(8) . . ?
C18 Ru2 C21 81.8(9) . . ?
C19 Ru2 C21 70.0(9) . . ?
C20 Ru2 C21 38.7(9) . . ?
C22 Ru2 C21 37.1(8) . . ?
C17 Ru2 C21 69.5(9) . . ?
O5 Ru2 Cl2 83.5(4) . . ?
N2 Ru2 Cl2 82.3(4) . . ?
C18 Ru2 Cl2 114.7(8) . . ?
C19 Ru2 Cl2 151.8(8) . . ?
C20 Ru2 Cl2 161.0(8) . . ?
C22 Ru2 Cl2 96.1(6) . . ?
C17 Ru2 Cl2 91.1(6) . . ?
C21 Ru2 Cl2 122.3(6) . . ?
C30 O5 Ru2 117.0(12) . . ?
C26 N2 Ru2 112.2(13) . . ?
C18 C17 C22 116(2) . . ?
C18 C17 C16 124(3) . . ?
C22 C17 C16 119(2) . . ?
C18 C17 Ru2 69.2(13) . . ?
C22 C17 Ru2 70.4(14) . . ?
C16 C17 Ru2 129.2(15) . . ?
C17 C18 C19 124(2) . . ?
C17 C18 Ru2 73.5(14) . . ?
C19 C18 Ru2 72.3(14) . . ?
C18 C19 C20 119(2) . . ?
C18 C19 Ru2 69.7(13) . . ?
C20 C19 Ru2 70.4(14) . . ?
C19 C20 C23 123(3) . . ?
C19 C20 C21 120(2) . . ?
C23 C20 C21 117(3) . . ?
C19 C20 Ru2 70.5(13) . . ?
C23 C20 Ru2 129(2) . . ?
C21 C20 Ru2 72.0(12) . . ?
C22 C21 C20 117(2) . . ?
C22 C21 Ru2 70.5(12) . . ?
C20 C21 Ru2 69.3(11) . . ?
C21 C22 C17 124(2) . . ?
C21 C22 Ru2 72.4(12) . . ?
C17 C22 Ru2 71.2(12) . . ?
C24 C23 C20 127(4) . . ?
C24 C23 C25 112(4) . . ?
C20 C23 C25 112(3) . . ?
N2 C26 C27 115.5(17) . . ?
N2 C26 C30 108.5(15) . . ?
C27 C26 C30 114.4(19) . . ?
C28 C27 C26 114.1(19) . . ?
C27 C28 C29 116(2) . . ?
O7 C29 O8 118(3) . . ?
O7 C29 C28 116(3) . . ?
O8 C29 C28 123(3) . . ?
O5 C30 O6 122.5(18) . . ?
O5 C30 C26 116.0(18) . . ?
O6 C30 C26 121.4(19) . . ?
O1 Ru1 N1 77.4(7) . . ?
O1 Ru1 C6 120.1(9) . . ?
N1 Ru1 C6 94.9(8) . . ?
O1 Ru1 C4 94.9(7) . . ?
N1 Ru1 C4 152.3(9) . . ?
C6 Ru1 C4 65.7(10) . . ?
O1 Ru1 C7 158.2(9) . . ?
N1 Ru1 C7 98.0(7) . . ?
C6 Ru1 C7 38.4(8) . . ?
C4 Ru1 C7 79.3(9) . . ?
O1 Ru1 C5 93.9(9) . . ?
N1 Ru1 C5 116.2(10) . . ?
C6 Ru1 C5 37.0(9) . . ?
C4 Ru1 C5 37.0(10) . . ?
C7 Ru1 C5 68.7(10) . . ?
O1 Ru1 C3 119.4(8) . . ?
N1 Ru1 C3 162.9(8) . . ?
C6 Ru1 C3 79.8(8) . . ?
C4 Ru1 C3 37.9(8) . . ?
C7 Ru1 C3 67.7(8) . . ?
C5 Ru1 C3 68.6(10) . . ?
O1 Ru1 C2 157.1(8) . . ?
N1 Ru1 C2 124.9(9) . . ?
C6 Ru1 C2 67.4(8) . . ?
C4 Ru1 C2 67.7(8) . . ?
C7 Ru1 C2 36.7(8) . . ?
C5 Ru1 C2 81.0(9) . . ?
C3 Ru1 C2 38.1(9) . . ?
O1 Ru1 Cl1 85.5(4) . . ?
N1 Ru1 Cl1 82.7(5) . . ?
C6 Ru1 Cl1 153.2(9) . . ?
C4 Ru1 Cl1 123.6(8) . . ?
C7 Ru1 Cl1 115.3(7) . . ?
C5 Ru1 Cl1 160.5(9) . . ?
C3 Ru1 Cl1 94.7(6) . . ?
C2 Ru1 Cl1 92.0(6) . . ?
C11 O1 Ru1 117.2(13) . . ?
C12 N1 Ru1 115.2(13) . . ?
C7 C2 C3 119(2) . . ?
C7 C2 C1 118(2) . . ?
C3 C2 C1 122(2) . . ?
C7 C2 Ru1 69.8(14) . . ?
C3 C2 Ru1 70.9(13) . . ?
C1 C2 Ru1 126.4(13) . . ?
C4 C3 C2 117(2) . . ?
C4 C3 Ru1 69.0(12) . . ?
C2 C3 Ru1 71.0(13) . . ?
C5 C4 C3 125(3) . . ?
C5 C4 Ru1 72.5(14) . . ?
C3 C4 Ru1 73.1(12) . . ?
C6 C5 C4 116(3) . . ?
C6 C5 C8 132(3) . . ?
C4 C5 C8 112(3) . . ?
C6 C5 Ru1 70.3(14) . . ?
C4 C5 Ru1 70.5(13) . . ?
C8 C5 Ru1 124.4(19) . . ?
C5 C6 C7 123(3) . . ?
C5 C6 Ru1 72.7(14) . . ?
C7 C6 Ru1 71.3(12) . . ?
C2 C7 C6 120(2) . . ?
C2 C7 Ru1 73.5(13) . . ?
C6 C7 Ru1 70.3(12) . . ?
C10 C8 C9 101(4) . . ?
C10 C8 C5 107(4) . . ?
C9 C8 C5 94(3) . . ?
O2 C11 O1 122.5(19) . . ?
O2 C11 C12 120(2) . . ?
O1 C11 C12 117.2(18) . . ?
N1 C12 C13 110(2) . . ?
N1 C12 C11 108.2(18) . . ?
C13 C12 C11 110(3) . . ?
C14 C13 C12 131(4) . . ?
C13 C14 C15 100(3) . . ?
O3 C15 O4 119(3) . . ?
O3 C15 C14 115(3) . . ?
O4 C15 C14 114(2) . . ?

_refine_diff_density_max         1.128
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_CA135_102
_audit_block_doi                 10.5517/cc13qcls
_database_code_depnum_ccdc_archive 'CCDC 1034395'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H31 Cl N2 Ru'
_chemical_formula_weight         423.98

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'
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                   9.8435(18)
_cell_length_b                   18.184(4)
_cell_length_c                   11.679(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.412(14)
_cell_angle_gamma                90
_cell_volume                     1932.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4132
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.28

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.951
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18241
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4719
_reflns_number_gt                2657
_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 AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0461P)²] 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         4719
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.018
_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
Ru1 Ru 0.20082(4) 0.92121(2) 0.22313(4) 0.03377(14) Uani 1 1 d . . . . .
Cl1 Cl -0.06325(13) 0.91276(8) 0.13113(13) 0.0467(4) Uani 1 1 d . . . . .
N1 N 0.2028(4) 0.8549(2) 0.0827(4) 0.0397(11) Uani 1 1 d . . . . .
N2 N 0.1760(4) 0.8086(2) 0.2849(4) 0.0404(10) Uani 1 1 d . . . . .
H2 H 0.0742 0.7972 0.2313 0.048 Uiso 1 1 calc R U . . .
C1 C 0.1847(6) 0.8670(4) -0.0364(5) 0.0514(15) Uani 1 1 d . . . . .
H1 H 0.1635 0.9120 -0.0774 0.062 Uiso 1 1 calc R U . . .
C2 C 0.2032(7) 0.8011(4) -0.0864(6) 0.0683(19) Uani 1 1 d . . . . .
H2A H 0.1968 0.7937 -0.1670 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2331(7) 0.7478(4) 0.0046(6) 0.0678(19) Uani 1 1 d . . . . .
H3 H 0.2495 0.6980 -0.0033 0.081 Uiso 1 1 calc R U . . .
C4 C 0.2336(6) 0.7825(3) 0.1075(5) 0.0483(14) Uani 1 1 d . . . . .
C5 C 0.2602(7) 0.7566(3) 0.2351(5) 0.0550(16) Uani 1 1 d . . . . .
H5A H 0.3643 0.7581 0.2863 0.066 Uiso 1 1 calc R U . . .
H5B H 0.2252 0.7066 0.2334 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1792(6) 0.7861(3) 0.4110(5) 0.0507(15) Uani 1 1 d . . . . .
C7 C 0.3342(6) 0.7891(4) 0.5090(5) 0.072(2) Uani 1 1 d . . . . .
H7A H 0.3734 0.8377 0.5119 0.107 Uiso 1 1 calc R U . . .
H7B H 0.3951 0.7544 0.4886 0.107 Uiso 1 1 calc R U . . .
H7C H 0.3321 0.7769 0.5882 0.107 Uiso 1 1 calc R U . . .
C8 C 0.0774(7) 0.8387(4) 0.4417(6) 0.0645(18) Uani 1 1 d . . . . .
H8A H -0.0202 0.8346 0.3798 0.097 Uiso 1 1 calc R U . . .
H8B H 0.1120 0.8882 0.4434 0.097 Uiso 1 1 calc R U . . .
H8C H 0.0763 0.8264 0.5213 0.097 Uiso 1 1 calc R U . . .
C9 C 0.1161(7) 0.7077(4) 0.4031(6) 0.080(2) Uani 1 1 d . . . . .
H9A H 0.1858 0.6727 0.3965 0.119 Uiso 1 1 calc R U . . .
H9B H 0.0262 0.7040 0.3315 0.119 Uiso 1 1 calc R U . . .
H9C H 0.0969 0.6977 0.4762 0.119 Uiso 1 1 calc R U . . .
C10 C 0.2897(6) 1.0159(3) 0.1638(5) 0.0421(13) Uani 1 1 d . . . . .
H10 H 0.2826 1.0297 0.0850 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4098(5) 0.9707(3) 0.2382(5) 0.0397(13) Uani 1 1 d . . . . .
C12 C 0.4156(6) 0.9516(3) 0.3551(5) 0.0470(14) Uani 1 1 d . . . . .
H12 H 0.4895 0.9205 0.4048 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3098(6) 0.9791(3) 0.3996(5) 0.0490(15) Uani 1 1 d . . . . .
H13 H 0.3183 0.9672 0.4795 0.059 Uiso 1 1 calc R U . . .
C14 C 0.1938(6) 1.0233(3) 0.3270(6) 0.0517(15) Uani 1 1 d . . . . .
C15 C 0.0756(7) 1.0496(4) 0.3713(7) 0.073(2) Uani 1 1 d . . . . .
H15A H 0.1157 1.0527 0.4601 0.110 Uiso 1 1 calc R U . . .
H15B H -0.0049 1.0154 0.3451 0.110 Uiso 1 1 calc R U . . .
H15C H 0.0413 1.0972 0.3369 0.110 Uiso 1 1 calc R U . . .
C16 C 0.1838(6) 1.0396(3) 0.2061(6) 0.0485(15) Uani 1 1 d . . . . .
H16 H 0.1045 1.0669 0.1538 0.058 Uiso 1 1 calc R U . . .
C17 C 0.5223(6) 0.9474(3) 0.1848(5) 0.0494(15) Uani 1 1 d . . . . .
H17 H 0.4695 0.9394 0.0958 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6263(8) 1.0120(4) 0.2002(7) 0.086(2) Uani 1 1 d . . . . .
H18A H 0.6933 1.0008 0.1607 0.129 Uiso 1 1 calc R U . . .
H18B H 0.6806 1.0209 0.2868 0.129 Uiso 1 1 calc R U . . .
H18C H 0.5706 1.0551 0.1629 0.129 Uiso 1 1 calc R U . . .
C19 C 0.6036(7) 0.8779(4) 0.2388(7) 0.086(2) Uani 1 1 d . . . . .
H19A H 0.6504 0.8829 0.3271 0.129 Uiso 1 1 calc R U . . .
H19B H 0.6767 0.8689 0.2047 0.129 Uiso 1 1 calc R U . . .
H19C H 0.5358 0.8375 0.2192 0.129 Uiso 1 1 calc R U . . .


_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
Ru1 N1 2.042(4) . ?
Ru1 C12 2.160(5) . ?
Ru1 C10 2.162(5) . ?
Ru1 C16 2.163(6) . ?
Ru1 C11 2.190(5) . ?
Ru1 C13 2.195(5) . ?
Ru1 N2 2.216(4) . ?
Ru1 C14 2.233(5) . ?
Ru1 Cl1 2.4093(14) . ?
N1 C1 1.351(6) . ?
N1 C4 1.357(7) . ?
N2 C5 1.511(6) . ?
N2 C6 1.517(6) . ?
N2 H2 0.9800 . ?
C1 C2 1.374(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.356(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.487(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.520(7) . ?
C6 C8 1.523(8) . ?
C6 C9 1.544(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C16 1.381(7) . ?
C10 C11 1.430(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(7) . ?
C11 C17 1.524(7) . ?
C12 C13 1.420(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(8) . ?
C13 H13 0.9300 . ?
C14 C16 1.409(8) . ?
C14 C15 1.520(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C17 C19 1.500(8) . ?
C17 C18 1.523(8) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 Ru1 C12 114.70(19) . . ?
N1 Ru1 C10 94.8(2) . . ?
C12 Ru1 C10 67.6(2) . . ?
N1 Ru1 C16 122.6(2) . . ?
C12 Ru1 C16 80.3(2) . . ?
C10 Ru1 C16 37.26(19) . . ?
N1 Ru1 C11 90.62(18) . . ?
C12 Ru1 C11 37.24(19) . . ?
C10 Ru1 C11 38.36(18) . . ?
C16 Ru1 C11 68.6(2) . . ?
N1 Ru1 C13 152.4(2) . . ?
C12 Ru1 C13 38.0(2) . . ?
C10 Ru1 C13 78.8(2) . . ?
C16 Ru1 C13 66.5(2) . . ?
C11 Ru1 C13 67.6(2) . . ?
N1 Ru1 N2 75.61(17) . . ?
C12 Ru1 N2 101.75(19) . . ?
C10 Ru1 N2 161.63(18) . . ?
C16 Ru1 N2 159.4(2) . . ?
C11 Ru1 N2 124.79(17) . . ?
C13 Ru1 N2 102.28(19) . . ?
N1 Ru1 C14 159.9(2) . . ?
C12 Ru1 C14 67.9(2) . . ?
C10 Ru1 C14 67.2(2) . . ?
C16 Ru1 C14 37.4(2) . . ?
C11 Ru1 C14 80.6(2) . . ?
C13 Ru1 C14 36.6(2) . . ?
N2 Ru1 C14 124.2(2) . . ?
N1 Ru1 Cl1 86.75(11) . . ?
C12 Ru1 Cl1 158.50(16) . . ?
C10 Ru1 Cl1 114.04(14) . . ?
C16 Ru1 Cl1 89.43(14) . . ?
C11 Ru1 Cl1 151.95(14) . . ?
C13 Ru1 Cl1 120.47(16) . . ?
N2 Ru1 Cl1 81.50(11) . . ?
C14 Ru1 Cl1 92.51(15) . . ?
C1 N1 C4 108.0(5) . . ?
C1 N1 Ru1 133.8(4) . . ?
C4 N1 Ru1 118.1(4) . . ?
C5 N2 C6 113.2(4) . . ?
C5 N2 Ru1 107.9(3) . . ?
C6 N2 Ru1 126.9(3) . . ?
C5 N2 H2 101.5 . . ?
C6 N2 H2 101.5 . . ?
Ru1 N2 H2 101.5 . . ?
N1 C1 C2 107.9(6) . . ?
N1 C1 H1 126.0 . . ?
C2 C1 H1 126.0 . . ?
C1 C2 C3 108.0(6) . . ?
C1 C2 H2A 126.0 . . ?
C3 C2 H2A 126.0 . . ?
C4 C3 C2 106.3(6) . . ?
C4 C3 H3 126.8 . . ?
C2 C3 H3 126.8 . . ?
C3 C4 N1 109.7(6) . . ?
C3 C4 C5 132.9(6) . . ?
N1 C4 C5 117.4(5) . . ?
C4 C5 N2 106.0(4) . . ?
C4 C5 H5A 110.5 . . ?
N2 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
N2 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
N2 C6 C7 111.4(5) . . ?
N2 C6 C8 106.8(4) . . ?
C7 C6 C8 111.2(5) . . ?
N2 C6 C9 109.3(5) . . ?
C7 C6 C9 110.1(5) . . ?
C8 C6 C9 107.9(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C16 C10 C11 121.6(5) . . ?
C16 C10 Ru1 71.4(3) . . ?
C11 C10 Ru1 71.9(3) . . ?
C16 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
Ru1 C10 H10 130.1 . . ?
C12 C11 C10 117.1(5) . . ?
C12 C11 C17 124.7(5) . . ?
C10 C11 C17 118.2(5) . . ?
C12 C11 Ru1 70.2(3) . . ?
C10 C11 Ru1 69.7(3) . . ?
C17 C11 Ru1 131.3(4) . . ?
C11 C12 C13 120.7(5) . . ?
C11 C12 Ru1 72.6(3) . . ?
C13 C12 Ru1 72.3(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
Ru1 C12 H12 127.6 . . ?
C14 C13 C12 121.8(5) . . ?
C14 C13 Ru1 73.2(3) . . ?
C12 C13 Ru1 69.7(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
Ru1 C13 H13 130.9 . . ?
C13 C14 C16 117.4(5) . . ?
C13 C14 C15 122.1(6) . . ?
C16 C14 C15 120.3(6) . . ?
C13 C14 Ru1 70.2(3) . . ?
C16 C14 Ru1 68.6(3) . . ?
C15 C14 Ru1 129.3(4) . . ?
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 . . ?
C10 C16 C14 121.3(5) . . ?
C10 C16 Ru1 71.3(3) . . ?
C14 C16 Ru1 74.0(3) . . ?
C10 C16 H16 119.4 . . ?
C14 C16 H16 119.4 . . ?
Ru1 C16 H16 127.4 . . ?
C19 C17 C18 111.9(6) . . ?
C19 C17 C11 114.6(5) . . ?
C18 C17 C11 107.4(5) . . ?
C19 C17 H17 107.6 . . ?
C18 C17 H17 107.6 . . ?
C11 C17 H17 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_CA11301
_audit_block_doi                 10.5517/cc13qcmt
_database_code_depnum_ccdc_archive 'CCDC 1034396'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Cl N2 Ru'
_chemical_formula_weight         453.96

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'
N N 0.0061 0.0033 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2603(18)
_cell_length_b                   15.897(3)
_cell_length_c                   13.222(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.976(12)
_cell_angle_gamma                90
_cell_volume                     2007.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8914
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      28.83

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.922
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            28193
_diffrn_reflns_av_unetI/netI     0.1517
_diffrn_reflns_av_R_equivalents  0.1925
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         28.831
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5210
_reflns_number_gt                2087
_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 AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0353P)²] 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         5210
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1852
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
Ru1 Ru 0.63292(5) 0.06453(3) 0.38113(4) 0.04939(18) Uani 1 1 d . . . . .
Cl1 Cl 0.54507(17) 0.16175(11) 0.46735(15) 0.0666(5) Uani 1 1 d . . . . .
N1 N 0.4297(5) 0.0478(3) 0.2436(5) 0.0593(14) Uani 1 1 d . . . . .
N2 N 0.5990(6) 0.1656(3) 0.2649(5) 0.0570(14) Uani 1 1 d . . . . .
C1 C 0.3277(7) -0.0083(5) 0.2151(7) 0.070(2) Uani 1 1 d . . . . .
H1 H 0.3351 -0.0551 0.2604 0.084 Uiso 1 1 calc R U . . .
C2 C 0.2094(8) 0.0145(6) 0.1076(7) 0.087(3) Uani 1 1 d . . . . .
H2 H 0.1244 -0.0140 0.0688 0.105 Uiso 1 1 calc R U . . .
C3 C 0.2399(8) 0.0873(6) 0.0681(7) 0.089(3) Uani 1 1 d . . . . .
H3 H 0.1812 0.1172 -0.0014 0.107 Uiso 1 1 calc R U . . .
C4 C 0.3764(7) 0.1054(5) 0.1547(6) 0.0641(19) Uani 1 1 d . . . . .
C5 C 0.4731(8) 0.1699(5) 0.1716(6) 0.068(2) Uani 1 1 d . . . . .
H5 H 0.4468 0.2138 0.1174 0.081 Uiso 1 1 calc R U . . .
C6 C 0.6998(8) 0.2335(4) 0.2906(6) 0.072(2) Uani 1 1 d . . . . .
H6A H 0.7382 0.2528 0.3718 0.087 Uiso 1 1 calc R U . . .
H6B H 0.6510 0.2805 0.2377 0.087 Uiso 1 1 calc R U . . .
C7 C 0.8175(7) 0.2069(4) 0.2759(6) 0.0603(17) Uani 1 1 d . . . . .
C8 C 0.9554(9) 0.2256(4) 0.3621(6) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.9754 0.2545 0.4306 0.086 Uiso 1 1 calc R U . . .
C9 C 1.0641(9) 0.2018(5) 0.3474(8) 0.088(2) Uani 1 1 d . . . . .
H9 H 1.1560 0.2141 0.4068 0.106 Uiso 1 1 calc R U . . .
C10 C 1.0381(10) 0.1613(5) 0.2489(10) 0.091(3) Uani 1 1 d . . . . .
H10 H 1.1117 0.1463 0.2398 0.109 Uiso 1 1 calc R U . . .
C11 C 0.9032(11) 0.1420(5) 0.1614(8) 0.090(3) Uani 1 1 d . . . . .
H11 H 0.8849 0.1140 0.0929 0.108 Uiso 1 1 calc R U . . .
C12 C 0.7947(8) 0.1646(4) 0.1758(7) 0.074(2) Uani 1 1 d . . . . .
H12 H 0.7035 0.1510 0.1163 0.089 Uiso 1 1 calc R U . . .
C13 C 0.5928(9) -0.0681(5) 0.1245(7) 0.112(3) Uani 1 1 d . . . . .
H13A H 0.5305 -0.0223 0.1113 0.167 Uiso 1 1 calc R U . . .
H13B H 0.5469 -0.1073 0.0596 0.167 Uiso 1 1 calc R U . . .
H13C H 0.6755 -0.0468 0.1295 0.167 Uiso 1 1 calc R U . . .
C14 C 0.7292(7) -0.1858(4) 0.2617(7) 0.090(2) Uani 1 1 d . . . . .
H14A H 0.8072 -0.1674 0.2568 0.136 Uiso 1 1 calc R U . . .
H14B H 0.6787 -0.2287 0.2031 0.136 Uiso 1 1 calc R U . . .
H14C H 0.7628 -0.2082 0.3398 0.136 Uiso 1 1 calc R U . . .
C15 C 0.6326(7) -0.1117(4) 0.2387(6) 0.0662(18) Uani 1 1 d . . . . .
H15 H 0.5464 -0.1342 0.2297 0.079 Uiso 1 1 calc R U . . .
C16 C 0.7004(6) -0.0565(4) 0.3475(5) 0.0515(15) Uani 1 1 d . . . . .
C17 C 0.7989(6) 0.0070(4) 0.3707(6) 0.0559(17) Uani 1 1 d . . . . .
H17 H 0.8121 0.0242 0.3061 0.067 Uiso 1 1 d R U . . .
C18 C 0.8645(6) 0.0551(4) 0.4775(6) 0.0564(16) Uani 1 1 d . . . . .
H18 H 0.9194 0.1048 0.4837 0.068 Uiso 1 1 d R U . . .
C19 C 0.8255(6) 0.0434(4) 0.5596(6) 0.0584(17) Uani 1 1 d . . . . .
C20 C 0.7242(6) -0.0173(4) 0.5384(5) 0.0535(16) Uani 1 1 d . . . . .
H20 H 0.6836 -0.0179 0.5882 0.064 Uiso 1 1 d R U . . .
C21 C 0.6648(6) -0.0668(4) 0.4361(5) 0.0532(15) Uani 1 1 d . . . . .
H21 H 0.5827 -0.1010 0.4161 0.064 Uiso 1 1 d R U . . .
C22 C 0.8900(7) 0.0973(4) 0.6703(6) 0.080(2) Uani 1 1 d . . . . .
H22A H 0.9626 0.0662 0.7365 0.119 Uiso 1 1 calc R U . . .
H22B H 0.8194 0.1128 0.6866 0.119 Uiso 1 1 calc R U . . .
H22C H 0.9290 0.1471 0.6581 0.119 Uiso 1 1 calc R U . . .


_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
Ru1 N1 2.051(5) . ?
Ru1 N2 2.114(5) . ?
Ru1 C17 2.150(6) . ?
Ru1 C21 2.178(6) . ?
Ru1 C20 2.193(6) . ?
Ru1 C16 2.199(6) . ?
Ru1 C18 2.220(6) . ?
Ru1 C19 2.228(6) . ?
Ru1 Cl1 2.4210(16) . ?
N1 C1 1.342(7) . ?
N1 C4 1.353(8) . ?
N2 C5 1.297(8) . ?
N2 C6 1.470(7) . ?
C1 C2 1.386(9) . ?
C2 C3 1.385(10) . ?
C3 C4 1.376(9) . ?
C4 C5 1.425(9) . ?
C6 C7 1.498(8) . ?
C7 C12 1.383(8) . ?
C7 C8 1.388(9) . ?
C8 C9 1.389(9) . ?
C9 C10 1.340(10) . ?
C10 C11 1.371(10) . ?
C11 C12 1.379(9) . ?
C13 C15 1.498(9) . ?
C14 C15 1.523(8) . ?
C15 C16 1.503(8) . ?
C16 C17 1.409(8) . ?
C16 C21 1.434(7) . ?
C17 C18 1.421(8) . ?
C18 C19 1.382(8) . ?
C19 C20 1.404(8) . ?
C19 C22 1.509(8) . ?
C20 C21 1.392(8) . ?

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 Ru1 N2 76.5(2) . . ?
N1 Ru1 C17 119.2(2) . . ?
N2 Ru1 C17 96.0(2) . . ?
N1 Ru1 C21 94.7(2) . . ?
N2 Ru1 C21 155.0(2) . . ?
C17 Ru1 C21 67.6(2) . . ?
N1 Ru1 C20 120.5(2) . . ?
N2 Ru1 C20 162.5(2) . . ?
C17 Ru1 C20 79.7(2) . . ?
C21 Ru1 C20 37.1(2) . . ?
N1 Ru1 C16 92.9(2) . . ?
N2 Ru1 C16 117.8(2) . . ?
C17 Ru1 C16 37.8(2) . . ?
C21 Ru1 C16 38.3(2) . . ?
C20 Ru1 C16 68.5(2) . . ?
N1 Ru1 C18 156.9(2) . . ?
N2 Ru1 C18 100.0(2) . . ?
C17 Ru1 C18 37.9(2) . . ?
C21 Ru1 C18 78.9(2) . . ?
C20 Ru1 C18 66.2(2) . . ?
C16 Ru1 C18 68.3(2) . . ?
N1 Ru1 C19 157.3(2) . . ?
N2 Ru1 C19 125.8(2) . . ?
C17 Ru1 C19 67.2(2) . . ?
C21 Ru1 C19 66.8(2) . . ?
C20 Ru1 C19 37.0(2) . . ?
C16 Ru1 C19 80.5(2) . . ?
C18 Ru1 C19 36.2(2) . . ?
N1 Ru1 Cl1 87.59(14) . . ?
N2 Ru1 Cl1 84.01(14) . . ?
C17 Ru1 Cl1 152.58(19) . . ?
C21 Ru1 Cl1 119.42(16) . . ?
C20 Ru1 Cl1 92.04(16) . . ?
C16 Ru1 Cl1 157.65(16) . . ?
C18 Ru1 Cl1 114.94(18) . . ?
C19 Ru1 Cl1 90.49(17) . . ?
C1 N1 C4 106.6(6) . . ?
C1 N1 Ru1 136.2(5) . . ?
C4 N1 Ru1 117.1(5) . . ?
C5 N2 C6 120.2(6) . . ?
C5 N2 Ru1 114.6(5) . . ?
C6 N2 Ru1 124.7(4) . . ?
N1 C1 C2 109.2(7) . . ?
C3 C2 C1 108.0(8) . . ?
C4 C3 C2 104.6(7) . . ?
N1 C4 C3 111.6(7) . . ?
N1 C4 C5 113.5(6) . . ?
C3 C4 C5 134.9(8) . . ?
N2 C5 C4 118.1(6) . . ?
N2 C6 C7 112.9(5) . . ?
C12 C7 C8 116.7(7) . . ?
C12 C7 C6 122.2(7) . . ?
C8 C7 C6 121.0(7) . . ?
C7 C8 C9 120.8(7) . . ?
C10 C9 C8 120.8(8) . . ?
C9 C10 C11 120.1(8) . . ?
C10 C11 C12 119.5(8) . . ?
C11 C12 C7 122.0(7) . . ?
C13 C15 C16 115.1(6) . . ?
C13 C15 C14 111.1(6) . . ?
C16 C15 C14 108.3(5) . . ?
C17 C16 C21 115.7(6) . . ?
C17 C16 C15 124.7(6) . . ?
C21 C16 C15 119.7(6) . . ?
C17 C16 Ru1 69.2(3) . . ?
C21 C16 Ru1 70.1(3) . . ?
C15 C16 Ru1 130.5(4) . . ?
C16 C17 C18 122.4(6) . . ?
C16 C17 Ru1 73.0(3) . . ?
C18 C17 Ru1 73.7(3) . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 Ru1 72.2(4) . . ?
C17 C18 Ru1 68.4(3) . . ?
C18 C19 C20 119.8(6) . . ?
C18 C19 C22 119.7(6) . . ?
C20 C19 C22 120.4(6) . . ?
C18 C19 Ru1 71.6(4) . . ?
C20 C19 Ru1 70.1(3) . . ?
C22 C19 Ru1 129.8(4) . . ?
C21 C20 C19 120.3(6) . . ?
C21 C20 Ru1 70.8(3) . . ?
C19 C20 Ru1 72.8(4) . . ?
C20 C21 C16 122.0(6) . . ?
C20 C21 Ru1 72.0(4) . . ?
C16 C21 Ru1 71.7(3) . . ?

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_CA249_1
_audit_block_doi                 10.5517/cc13qcnv
_database_code_depnum_ccdc_archive 'CCDC 1034397'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Cl N2 O Ru'
_chemical_formula_weight         446.95

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           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                   9.5877(12)
_cell_length_b                   15.183(2)
_cell_length_c                   13.9495(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.417(9)
_cell_angle_gamma                90
_cell_volume                     2017.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7765
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      28.69

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.919
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8234
_exptl_absorpt_correction_T_max  0.8448
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            20381
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.989
_diffrn_reflns_theta_max         28.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5147
_reflns_number_gt                3129
_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 AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0667P)²+2.9614P] 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         5147
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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
Ru1 Ru 0.34077(4) 0.95141(3) 0.15689(3) 0.05155(17) Uani 1 1 d . . . . .
Cl1 Cl 0.28425(15) 0.89393(11) -0.00420(10) 0.0682(4) Uani 1 1 d . . . . .
O1 O -0.0246(14) 0.9486(6) 0.3339(7) 0.223(6) Uani 1 1 d . . . . .
N1 N 0.2782(4) 1.0722(3) 0.1025(3) 0.0544(11) Uani 1 1 d . . . . .
N2 N 0.1206(5) 0.9500(3) 0.1604(3) 0.0591(12) Uani 1 1 d . . . . .
C9 C -0.1709(12) 0.8339(11) 0.3743(10) 0.173(7) Uani 1 1 d . . . . .
H9A H -0.1568 0.7905 0.4255 0.207 Uiso 1 1 calc R U . . .
H9B H -0.2709 0.8406 0.3559 0.207 Uiso 1 1 calc R U . . .
C15 C 0.4636(6) 1.0093(4) 0.2807(4) 0.0603(14) Uani 1 1 d . . . . .
C1 C 0.3385(6) 1.1449(4) 0.0724(4) 0.0629(14) Uani 1 1 d . . . . .
H1 H 0.4345 1.1520 0.0705 0.076 Uiso 1 1 calc R U . . .
C2 C 0.2376(7) 1.2085(5) 0.0443(4) 0.0731(17) Uani 1 1 d . . . . .
H2 H 0.2537 1.2646 0.0210 0.088 Uiso 1 1 calc R U . . .
C3 C 0.1079(6) 1.1721(4) 0.0577(4) 0.0674(16) Uani 1 1 d . . . . .
H3 H 0.0204 1.1986 0.0449 0.081 Uiso 1 1 calc R U . . .
C4 C 0.1361(5) 1.0881(4) 0.0940(4) 0.0569(13) Uani 1 1 d . . . . .
C5 C 0.0573(6) 1.0181(4) 0.1244(4) 0.0625(15) Uani 1 1 d . . . . .
H5 H -0.0402 1.0212 0.1184 0.075 Uiso 1 1 calc R U . . .
C6 C 0.0383(7) 0.8746(5) 0.1879(5) 0.0790(19) Uani 1 1 d . . . . .
H6 H 0.0258 0.8250 0.1488 0.095 Uiso 1 1 calc R U . . .
C7 C -0.0184(18) 0.8794(8) 0.2716(11) 0.220(8) Uani 1 1 d . . . . .
H7 H 0.0656 0.8549 0.3086 0.264 Uiso 1 1 calc R U . . .
C10 C -0.1116(18) 0.9143(13) 0.4054(10) 0.210(7) Uani 1 1 d . . . . .
H10A H -0.0546 0.9064 0.4668 0.252 Uiso 1 1 calc R U . . .
H10B H -0.1854 0.9561 0.4146 0.252 Uiso 1 1 calc R U . . .
C8 C -0.1051(10) 0.8077(6) 0.2961(8) 0.124(3) Uani 1 1 d . . . . .
H8A H -0.1741 0.7935 0.2421 0.149 Uiso 1 1 calc R U . . .
H8B H -0.0482 0.7558 0.3123 0.149 Uiso 1 1 calc R U . . .
C12 C 0.4915(6) 0.8407(4) 0.1932(4) 0.0640(15) Uani 1 1 d . . . . .
C13 C 0.4088(6) 0.8513(5) 0.2690(4) 0.0688(16) Uani 1 1 d . . . . .
H13 H 0.3434 0.8044 0.2820 0.083 Uiso 1 1 calc R U . . .
C14 C 0.3921(7) 0.9357(4) 0.3089(4) 0.0669(16) Uani 1 1 d . . . . .
H14 H 0.3179 0.9442 0.3509 0.080 Uiso 1 1 calc R U . . .
C18 C 0.4555(8) 1.0986(5) 0.3262(5) 0.0789(19) Uani 1 1 d . . . . .
H18 H 0.4633 1.1426 0.2757 0.095 Uiso 1 1 calc R U . . .
C19 C 0.5717(13) 1.1115(8) 0.3991(9) 0.184(6) Uani 1 1 d . . . . .
H19A H 0.5707 1.0667 0.4476 0.276 Uiso 1 1 calc R U . . .
H19B H 0.5641 1.1684 0.4282 0.276 Uiso 1 1 calc R U . . .
H19C H 0.6579 1.1082 0.3704 0.276 Uiso 1 1 calc R U . . .
C20 C 0.3124(12) 1.1133(7) 0.3661(9) 0.164(5) Uani 1 1 d . . . . .
H20A H 0.2898 1.0625 0.4024 0.247 Uiso 1 1 calc R U . . .
H20B H 0.2405 1.1223 0.3134 0.247 Uiso 1 1 calc R U . . .
H20C H 0.3185 1.1641 0.4073 0.247 Uiso 1 1 calc R U . . .
C16 C 0.5517(5) 0.9970(4) 0.2058(4) 0.0592(14) Uani 1 1 d . . . . .
H16 H 0.5871 1.0493 0.1751 0.071 Uiso 1 1 calc R U . . .
C17 C 0.5622(5) 0.9158(4) 0.1612(4) 0.0605(14) Uani 1 1 d . . . . .
H17 H 0.6051 0.9125 0.1008 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5059(8) 0.7524(5) 0.1447(6) 0.091(2) Uani 1 1 d . . . . .
H11A H 0.4230 0.7179 0.1496 0.137 Uiso 1 1 calc R U . . .
H11B H 0.5863 0.7219 0.1758 0.137 Uiso 1 1 calc R U . . .
H11C H 0.5174 0.7614 0.0779 0.137 Uiso 1 1 calc R U . . .


_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
Ru1 N1 2.048(5) . ?
Ru1 N2 2.117(4) . ?
Ru1 C14 2.136(6) . ?
Ru1 C15 2.166(5) . ?
Ru1 C16 2.174(5) . ?
Ru1 C17 2.185(5) . ?
Ru1 C13 2.225(6) . ?
Ru1 C12 2.238(6) . ?
Ru1 Cl1 2.4151(14) . ?
O1 C7 1.369(12) . ?
O1 C10 1.466(13) . ?
N1 C1 1.336(7) . ?
N1 C4 1.376(6) . ?
N2 C5 1.274(7) . ?
N2 C6 1.465(7) . ?
C9 C8 1.378(16) . ?
C9 C10 1.395(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 C14 1.390(8) . ?
C15 C16 1.427(8) . ?
C15 C18 1.502(9) . ?
C1 C2 1.392(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.343(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.435(11) . ?
C7 H7 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C13 1.400(8) . ?
C12 C17 1.424(8) . ?
C12 C11 1.515(9) . ?
C13 C14 1.413(9) . ?
C13 H13 0.9800 . ?
C14 H14 0.9800 . ?
C18 C19 1.435(10) . ?
C18 C20 1.553(11) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 C17 1.390(8) . ?
C16 H16 0.9800 . ?
C17 H17 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 Ru1 N2 76.48(18) . . ?
N1 Ru1 C14 119.5(2) . . ?
N2 Ru1 C14 95.5(2) . . ?
N1 Ru1 C15 92.4(2) . . ?
N2 Ru1 C15 116.1(2) . . ?
C14 Ru1 C15 37.7(2) . . ?
N1 Ru1 C16 93.1(2) . . ?
N2 Ru1 C16 153.0(2) . . ?
C14 Ru1 C16 67.7(2) . . ?
C15 Ru1 C16 38.4(2) . . ?
N1 Ru1 C17 118.4(2) . . ?
N2 Ru1 C17 164.8(2) . . ?
C14 Ru1 C17 80.2(2) . . ?
C15 Ru1 C17 68.8(2) . . ?
C16 Ru1 C17 37.2(2) . . ?
N1 Ru1 C13 157.2(2) . . ?
N2 Ru1 C13 101.0(2) . . ?
C14 Ru1 C13 37.7(2) . . ?
C15 Ru1 C13 68.0(2) . . ?
C16 Ru1 C13 78.9(2) . . ?
C17 Ru1 C13 66.7(2) . . ?
N1 Ru1 C12 155.7(2) . . ?
N2 Ru1 C12 127.4(2) . . ?
C14 Ru1 C12 67.7(2) . . ?
C15 Ru1 C12 81.1(2) . . ?
C16 Ru1 C12 67.3(2) . . ?
C17 Ru1 C12 37.5(2) . . ?
C13 Ru1 C12 36.6(2) . . ?
N1 Ru1 Cl1 87.31(13) . . ?
N2 Ru1 Cl1 84.12(12) . . ?
C14 Ru1 Cl1 152.41(19) . . ?
C15 Ru1 Cl1 159.14(16) . . ?
C16 Ru1 Cl1 120.75(15) . . ?
C17 Ru1 Cl1 93.01(16) . . ?
C13 Ru1 Cl1 115.14(19) . . ?
C12 Ru1 Cl1 90.65(16) . . ?
C7 O1 C10 103.2(10) . . ?
C1 N1 C4 106.7(5) . . ?
C1 N1 Ru1 137.5(4) . . ?
C4 N1 Ru1 115.8(4) . . ?
C5 N2 C6 119.4(5) . . ?
C5 N2 Ru1 114.5(4) . . ?
C6 N2 Ru1 125.5(4) . . ?
C8 C9 C10 107.0(9) . . ?
C8 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
C14 C15 C16 116.9(6) . . ?
C14 C15 C18 123.7(6) . . ?
C16 C15 C18 119.3(6) . . ?
C14 C15 Ru1 70.0(3) . . ?
C16 C15 Ru1 71.1(3) . . ?
C18 C15 Ru1 130.8(4) . . ?
N1 C1 C2 110.5(5) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C3 C2 C1 106.8(6) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C4 C3 C2 105.9(5) . . ?
C4 C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
N1 C4 C3 110.1(5) . . ?
N1 C4 C5 113.8(5) . . ?
C3 C4 C5 136.1(5) . . ?
N2 C5 C4 119.2(5) . . ?
N2 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 N2 117.8(7) . . ?
C7 C6 H6 121.1 . . ?
N2 C6 H6 121.1 . . ?
C6 C7 O1 130.1(9) . . ?
C6 C7 C8 117.9(10) . . ?
O1 C7 C8 111.3(9) . . ?
C6 C7 H7 92.8 . . ?
O1 C7 H7 92.8 . . ?
C8 C7 H7 92.8 . . ?
C9 C10 O1 110.0(11) . . ?
C9 C10 H10A 109.7 . . ?
O1 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
O1 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C9 C8 C7 107.3(10) . . ?
C9 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C13 C12 C17 118.3(6) . . ?
C13 C12 C11 121.8(6) . . ?
C17 C12 C11 119.9(6) . . ?
C13 C12 Ru1 71.2(3) . . ?
C17 C12 Ru1 69.2(3) . . ?
C11 C12 Ru1 130.7(4) . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 Ru1 72.2(3) . . ?
C14 C13 Ru1 67.7(3) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
Ru1 C13 H13 118.9 . . ?
C15 C14 C13 122.4(6) . . ?
C15 C14 Ru1 72.3(3) . . ?
C13 C14 Ru1 74.6(4) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
Ru1 C14 H14 118.5 . . ?
C15 C18 C19 110.5(7) . . ?
C15 C18 C20 111.8(7) . . ?
C19 C18 C20 111.9(9) . . ?
C15 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C20 C18 H18 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C16 C15 121.5(6) . . ?
C17 C16 Ru1 71.9(3) . . ?
C15 C16 Ru1 70.5(3) . . ?
C17 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
Ru1 C16 H16 118.5 . . ?
C16 C17 C12 120.6(5) . . ?
C16 C17 Ru1 70.9(3) . . ?
C12 C17 Ru1 73.2(3) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
Ru1 C17 H17 119.3 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_CA18401
_audit_block_doi                 10.5517/cc13qcpw
_database_code_depnum_ccdc_archive 'CCDC 1034398'
_audit_update_record             
;
2015-07-19 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 Cl N2 O Ru'
_chemical_formula_weight         505.07

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.010(7)
_cell_length_b                   11.237(5)
_cell_length_c                   13.004(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.50(3)
_cell_angle_gamma                90
_cell_volume                     2484.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      28.28

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.755
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            34152
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6159
_reflns_number_gt                2985
_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 AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0711P)²+0.4050P] 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         6159
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1293
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
Ru1 Ru 0.74373(2) 0.33947(3) 0.49334(3) 0.06697(18) Uani 1 1 d . . . . .
Cl1 Cl 0.84462(9) 0.30222(15) 0.62319(10) 0.0905(4) Uani 1 1 d . . . . .
N1 N 0.7289(2) 0.1471(3) 0.4934(3) 0.0681(11) Uani 1 1 d . . . . .
C10 C 0.9314(5) 0.5646(7) 0.3225(7) 0.162(3) Uani 1 1 d . . . . .
H10A H 0.9862 0.5846 0.3290 0.243 Uiso 1 1 calc R U . . .
H10B H 0.9002 0.6335 0.3371 0.243 Uiso 1 1 calc R U . . .
H10C H 0.9196 0.5379 0.2537 0.243 Uiso 1 1 calc R U . . .
N2 N 0.6597(2) 0.3039(4) 0.6009(3) 0.0705(11) Uani 1 1 d . . . . .
C2 C 0.6553(4) 0.4353(5) 0.4001(4) 0.0874(17) Uani 1 1 d . . . . .
C1 C 0.5672(3) 0.4252(6) 0.4050(5) 0.114(2) Uani 1 1 d . . . . .
H1A H 0.5497 0.3568 0.3665 0.171 Uiso 1 1 calc R U . . .
H1B H 0.5433 0.4955 0.3763 0.171 Uiso 1 1 calc R U . . .
H1C H 0.5525 0.4167 0.4754 0.171 Uiso 1 1 calc R U . . .
C3 C 0.6965(4) 0.5150(5) 0.4649(5) 0.0949(18) Uani 1 1 d . . . . .
H3 H 0.6679 0.5541 0.5199 0.114 Uiso 1 1 calc R U . . .
C4 C 0.7790(4) 0.5223(5) 0.4671(4) 0.0950(18) Uani 1 1 d . . . . .
H4 H 0.8056 0.5663 0.5229 0.114 Uiso 1 1 calc R U . . .
C5 C 0.8246(4) 0.4509(5) 0.4007(4) 0.0818(15) Uani 1 1 d . . . . .
C6 C 0.7834(3) 0.3729(4) 0.3337(3) 0.0709(13) Uani 1 1 d . . . . .
H6 H 0.8130 0.3103 0.2993 0.085 Uiso 1 1 calc R U . . .
C7 C 0.7008(3) 0.3631(5) 0.3356(4) 0.0744(14) Uani 1 1 d . . . . .
H7 H 0.6754 0.2957 0.3004 0.089 Uiso 1 1 calc R U . . .
C8 C 0.9123(4) 0.4646(6) 0.3993(5) 0.1023(19) Uani 1 1 d . . . . .
H8 H 0.9300 0.4913 0.4678 0.123 Uiso 1 1 calc R U . . .
C9 C 0.9594(4) 0.3572(6) 0.3733(6) 0.121(2) Uani 1 1 d . . . . .
H9A H 0.9513 0.2964 0.4238 0.181 Uiso 1 1 calc R U . . .
H9B H 1.0141 0.3778 0.3727 0.181 Uiso 1 1 calc R U . . .
H9C H 0.9430 0.3283 0.3066 0.181 Uiso 1 1 calc R U . . .
C11 C 0.6217(3) 0.3735(5) 0.6703(4) 0.0802(15) Uani 1 1 d . . . . .
H11 H 0.6383 0.4477 0.6941 0.096 Uiso 1 1 calc R U . . .
C12 C 0.5550(4) 0.3148(6) 0.6988(5) 0.0980(19) Uani 1 1 d . . . . .
H12 H 0.5191 0.3420 0.7461 0.118 Uiso 1 1 calc R U . . .
C13 C 0.5501(3) 0.2074(6) 0.6448(5) 0.0938(17) Uani 1 1 d . . . . .
H13 H 0.5106 0.1504 0.6483 0.113 Uiso 1 1 calc R U . . .
C14 C 0.6160(3) 0.2037(5) 0.5851(4) 0.0749(14) Uani 1 1 d . . . . .
C15 C 0.6430(3) 0.1199(5) 0.5040(4) 0.0805(15) Uani 1 1 d . . . . .
H15 H 0.6159 0.1410 0.4392 0.097 Uiso 1 1 calc R U . . .
C20 C 0.7662(3) 0.0800(5) 0.4073(4) 0.0843(16) Uani 1 1 d . . . . .
H20A H 0.7377 0.0062 0.3955 0.101 Uiso 1 1 calc R U . . .
H20B H 0.7619 0.1269 0.3448 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8488(4) 0.0531(6) 0.4293(5) 0.104(2) Uani 1 1 d . . . . .
H21 H 0.8778 0.1276 0.4399 0.125 Uiso 1 1 calc R U . . .
O1 O 0.8569(3) -0.0192(4) 0.5204(4) 0.1202(15) Uani 1 1 d . . . . .
C24 C 0.8916(6) -0.1239(8) 0.4950(8) 0.176(4) Uani 1 1 d . . . . .
H24A H 0.8522 -0.1861 0.4884 0.211 Uiso 1 1 calc R U . . .
H24B H 0.9295 -0.1470 0.5484 0.211 Uiso 1 1 calc R U . . .
C23 C 0.9308(7) -0.1081(9) 0.3979(8) 0.193(5) Uani 1 1 d . . . . .
H23A H 0.9848 -0.0826 0.4098 0.231 Uiso 1 1 calc R U . . .
H23B H 0.9309 -0.1820 0.3593 0.231 Uiso 1 1 calc R U . . .
C22 C 0.8867(5) -0.0184(8) 0.3432(6) 0.143(3) Uani 1 1 d . . . . .
H22A H 0.8471 -0.0538 0.2978 0.172 Uiso 1 1 calc R U . . .
H22B H 0.9209 0.0315 0.3031 0.172 Uiso 1 1 calc R U . . .
C16 C 0.6239(3) -0.0106(6) 0.5278(5) 0.0987(19) Uani 1 1 d . . . . .
H16A H 0.5675 -0.0176 0.5355 0.118 Uiso 1 1 calc R U . . .
H16B H 0.6379 -0.0585 0.4690 0.118 Uiso 1 1 calc R U . . .
C17 C 0.6641(4) -0.0621(5) 0.6224(5) 0.0969(18) Uani 1 1 d . . . . .
H17A H 0.6455 -0.0208 0.6826 0.116 Uiso 1 1 calc R U . . .
H17B H 0.7203 -0.0480 0.6187 0.116 Uiso 1 1 calc R U . . .
C18 C 0.6501(6) -0.1949(6) 0.6355(7) 0.145(3) Uani 1 1 d . . . . .
H18A H 0.5939 -0.2088 0.6377 0.174 Uiso 1 1 calc R U . . .
H18B H 0.6694 -0.2359 0.5756 0.174 Uiso 1 1 calc R U . . .
C19 C 0.6882(7) -0.2481(7) 0.7297(8) 0.202(5) Uani 1 1 d . . . . .
H19A H 0.7437 -0.2325 0.7298 0.303 Uiso 1 1 calc R U . . .
H19B H 0.6794 -0.3325 0.7299 0.303 Uiso 1 1 calc R U . . .
H19C H 0.6660 -0.2134 0.7898 0.303 Uiso 1 1 calc R U . . .


_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
Ru1 N2 2.065(4) . ?
Ru1 C3 2.158(5) . ?
Ru1 C4 2.170(6) . ?
Ru1 C7 2.175(5) . ?
Ru1 N1 2.177(4) . ?
Ru1 C2 2.190(5) . ?
Ru1 C6 2.231(5) . ?
Ru1 C5 2.236(6) . ?
Ru1 Cl1 2.4123(16) . ?
N1 C15 1.503(6) . ?
N1 C20 1.504(5) . ?
C10 C8 1.543(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N2 C14 1.362(7) . ?
N2 C11 1.369(6) . ?
C2 C3 1.406(8) . ?
C2 C7 1.411(7) . ?
C2 C1 1.506(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.405(9) . ?
C3 H3 0.9800 . ?
C4 C5 1.423(8) . ?
C4 H4 0.9800 . ?
C5 C6 1.410(7) . ?
C5 C8 1.500(8) . ?
C6 C7 1.410(7) . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.492(9) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.372(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.495(7) . ?
C15 C16 1.534(8) . ?
C15 H15 0.9800 . ?
C20 C21 1.458(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O1 1.440(7) . ?
C21 C22 1.534(8) . ?
C21 H21 0.9800 . ?
O1 C24 1.360(8) . ?
C24 C23 1.455(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 C22 1.434(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C16 C17 1.508(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.521(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.495(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
N2 Ru1 C3 91.8(2) . . ?
N2 Ru1 C4 119.3(2) . . ?
C3 Ru1 C4 37.9(2) . . ?
N2 Ru1 C7 116.18(19) . . ?
C3 Ru1 C7 67.2(2) . . ?
C4 Ru1 C7 79.8(2) . . ?
N2 Ru1 N1 74.07(15) . . ?
C3 Ru1 N1 149.9(2) . . ?
C4 Ru1 N1 166.7(2) . . ?
C7 Ru1 N1 94.92(17) . . ?
N2 Ru1 C2 89.58(19) . . ?
C3 Ru1 C2 37.7(2) . . ?
C4 Ru1 C2 68.7(2) . . ?
C7 Ru1 C2 37.72(18) . . ?
N1 Ru1 C2 114.2(2) . . ?
N2 Ru1 C6 153.42(18) . . ?
C3 Ru1 C6 78.9(2) . . ?
C4 Ru1 C6 66.6(2) . . ?
C7 Ru1 C6 37.29(18) . . ?
N1 Ru1 C6 101.85(16) . . ?
C2 Ru1 C6 67.8(2) . . ?
N2 Ru1 C5 156.91(19) . . ?
C3 Ru1 C5 68.1(2) . . ?
C4 Ru1 C5 37.6(2) . . ?
C7 Ru1 C5 67.6(2) . . ?
N1 Ru1 C5 129.01(18) . . ?
C2 Ru1 C5 81.4(2) . . ?
C6 Ru1 C5 36.80(18) . . ?
N2 Ru1 Cl1 89.12(12) . . ?
C3 Ru1 Cl1 122.2(2) . . ?
C4 Ru1 Cl1 94.59(18) . . ?
C7 Ru1 Cl1 153.66(15) . . ?
N1 Ru1 Cl1 84.71(11) . . ?
C2 Ru1 Cl1 159.82(18) . . ?
C6 Ru1 Cl1 116.97(14) . . ?
C5 Ru1 Cl1 92.17(15) . . ?
C15 N1 C20 113.4(4) . . ?
C15 N1 Ru1 108.4(3) . . ?
C20 N1 Ru1 116.5(3) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 N2 C11 107.8(5) . . ?
C14 N2 Ru1 116.3(3) . . ?
C11 N2 Ru1 133.1(4) . . ?
C3 C2 C7 116.7(6) . . ?
C3 C2 C1 120.3(6) . . ?
C7 C2 C1 122.9(6) . . ?
C3 C2 Ru1 69.9(3) . . ?
C7 C2 Ru1 70.6(3) . . ?
C1 C2 Ru1 127.5(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C3 C4 122.1(5) . . ?
C2 C3 Ru1 72.4(3) . . ?
C4 C3 Ru1 71.5(3) . . ?
C2 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
Ru1 C3 H3 118.3 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 Ru1 70.6(3) . . ?
C5 C4 Ru1 73.7(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
Ru1 C4 H4 119.0 . . ?
C6 C5 C4 117.0(5) . . ?
C6 C5 C8 122.3(5) . . ?
C4 C5 C8 120.6(5) . . ?
C6 C5 Ru1 71.4(3) . . ?
C4 C5 Ru1 68.6(3) . . ?
C8 C5 Ru1 133.6(4) . . ?
C5 C6 C7 121.2(5) . . ?
C5 C6 Ru1 71.8(3) . . ?
C7 C6 Ru1 69.2(3) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
Ru1 C6 H6 118.4 . . ?
C6 C7 C2 121.9(5) . . ?
C6 C7 Ru1 73.5(3) . . ?
C2 C7 Ru1 71.7(3) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
Ru1 C7 H7 118.6 . . ?
C9 C8 C5 117.4(6) . . ?
C9 C8 C10 108.6(6) . . ?
C5 C8 C10 108.0(6) . . ?
C9 C8 H8 107.5 . . ?
C5 C8 H8 107.5 . . ?
C10 C8 H8 107.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C11 C12 108.1(5) . . ?
N2 C11 H11 125.9 . . ?
C12 C11 H11 125.9 . . ?
C11 C12 C13 108.6(5) . . ?
C11 C12 H12 125.7 . . ?
C13 C12 H12 125.7 . . ?
C14 C13 C12 105.6(6) . . ?
C14 C13 H13 127.2 . . ?
C12 C13 H13 127.2 . . ?
N2 C14 C13 109.8(5) . . ?
N2 C14 C15 116.8(5) . . ?
C13 C14 C15 133.2(6) . . ?
C14 C15 N1 104.7(4) . . ?
C14 C15 C16 112.9(5) . . ?
N1 C15 C16 115.1(4) . . ?
C14 C15 H15 107.9 . . ?
N1 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C21 C20 N1 112.3(4) . . ?
C21 C20 H20A 109.1 . . ?
N1 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
N1 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
O1 C21 C20 110.5(5) . . ?
O1 C21 C22 105.8(5) . . ?
C20 C21 C22 112.7(6) . . ?
O1 C21 H21 109.2 . . ?
C20 C21 H21 109.2 . . ?
C22 C21 H21 109.2 . . ?
C24 O1 C21 108.8(6) . . ?
O1 C24 C23 108.5(7) . . ?
O1 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
O1 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
C22 C23 C24 105.7(8) . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23B 110.6 . . ?
C24 C23 H23B 110.6 . . ?
H23A C23 H23B 108.7 . . ?
C23 C22 C21 103.3(7) . . ?
C23 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C17 C16 C15 115.9(5) . . ?
C17 C16 H16A 108.3 . . ?
C15 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C16 C17 C18 113.5(6) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 114.7(7) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.832
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.067

