# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_e2
_database_code_depnum_ccdc_archive 'CCDC 1578919'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42

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'

_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                   13.9786(18)
_cell_length_b                   5.8864(6)
_cell_length_c                   22.939(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.038(4)
_cell_angle_gamma                90
_cell_volume                     1869.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9750
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61178
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4668
_reflns_number_gt                3102
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0627P)²+1.0759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0135(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4668
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.005
_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
N1 N 0.04757(11) 0.4688(3) 0.08315(7) 0.0474(4) Uani 1 1 d . . . . .
O1 O 0.26979(11) -0.0647(2) -0.08977(7) 0.0595(4) Uani 1 1 d . . . . .
H1A H 0.322(2) 0.008(5) -0.1054(12) 0.089 Uiso 1 1 d . U . . .
C1 C -0.07003(14) 0.5722(4) 0.14408(9) 0.0529(5) Uani 1 1 d . . . . .
H1 H -0.1012 0.4359 0.1333 0.063 Uiso 1 1 calc R U . . .
N2 N 0.12220(11) 0.5302(3) 0.06290(7) 0.0470(4) Uani 1 1 d . . . . .
C2 C -0.10757(16) 0.7204(5) 0.18198(10) 0.0640(6) Uani 1 1 d . . . . .
H2 H -0.1645 0.6832 0.1965 0.077 Uiso 1 1 calc R U . . .
N3 N 0.39510(11) 0.2518(3) -0.10458(7) 0.0471(4) Uani 1 1 d . . . . .
C3 C -0.06192(18) 0.9211(5) 0.19843(10) 0.0661(6) Uani 1 1 d . . . . .
H3 H -0.0876 1.0189 0.2240 0.079 Uiso 1 1 calc R U . . .
C4 C 0.02225(18) 0.9778(4) 0.17689(10) 0.0640(6) Uani 1 1 d . . . . .
H4 H 0.0531 1.1142 0.1879 0.077 Uiso 1 1 calc R U . . .
C5 C 0.06081(15) 0.8329(4) 0.13906(9) 0.0537(5) Uani 1 1 d . . . . .
H5 H 0.1177 0.8711 0.1247 0.064 Uiso 1 1 calc R U . . .
C6 C 0.01436(13) 0.6297(3) 0.12257(8) 0.0447(4) Uani 1 1 d . . . . .
C7 C 0.15681(12) 0.3710(3) 0.02412(8) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.11573(13) 0.1569(3) 0.01068(8) 0.0461(4) Uani 1 1 d . . . . .
H8 H 0.0624 0.1112 0.0279 0.055 Uiso 1 1 calc R U . . .
C9 C 0.15331(14) 0.0144(3) -0.02752(9) 0.0471(4) Uani 1 1 d . . . . .
H9 H 0.1252 -0.1268 -0.0364 0.057 Uiso 1 1 calc R U . . .
C10 C 0.23368(13) 0.0809(3) -0.05301(8) 0.0421(4) Uani 1 1 d . . . . .
C11 C 0.27568(12) 0.2961(3) -0.04033(7) 0.0384(4) Uani 1 1 d . . . . .
C12 C 0.23643(12) 0.4374(3) -0.00109(8) 0.0410(4) Uani 1 1 d . . . . .
H12 H 0.2643 0.5786 0.0083 0.049 Uiso 1 1 calc R U . . .
C13 C 0.35802(13) 0.3730(3) -0.06725(8) 0.0437(4) Uani 1 1 d . . . . .
H13 H 0.3846 0.5148 -0.0570 0.052 Uiso 1 1 calc R U . . .
C14 C 0.47559(13) 0.3409(3) -0.12989(8) 0.0459(4) Uani 1 1 d . . . . .
C15 C 0.46356(15) 0.5200(4) -0.17008(9) 0.0535(5) Uani 1 1 d . . . . .
C16 C 0.54505(17) 0.5979(4) -0.19294(10) 0.0630(6) Uani 1 1 d . . . . .
H16 H 0.5383 0.7174 -0.2197 0.076 Uiso 1 1 calc R U . . .
C17 C 0.63500(16) 0.5039(5) -0.17717(10) 0.0640(6) Uani 1 1 d . . . . .
C18 C 0.64369(15) 0.3234(5) -0.13859(9) 0.0613(6) Uani 1 1 d . . . . .
H18 H 0.7041 0.2571 -0.1282 0.074 Uiso 1 1 calc R U . . .
C19 C 0.56514(14) 0.2370(4) -0.11463(8) 0.0520(5) Uani 1 1 d . . . . .
C20 C 0.36689(18) 0.6273(5) -0.19087(11) 0.0736(7) Uani 1 1 d . . . . .
H20A H 0.3192 0.5650 -0.1691 0.110 Uiso 1 1 calc R U . . .
H20B H 0.3488 0.5967 -0.2320 0.110 Uiso 1 1 calc R U . . .
H20C H 0.3711 0.7885 -0.1847 0.110 Uiso 1 1 calc R U . . .
C21 C 0.7229(2) 0.5969(6) -0.20124(14) 0.0956(10) Uani 1 1 d . . . . .
H21A H 0.7048 0.6433 -0.2414 0.143 Uiso 1 1 calc R U . . .
H21B H 0.7716 0.4811 -0.1994 0.143 Uiso 1 1 calc R U . . .
H21C H 0.7479 0.7251 -0.1781 0.143 Uiso 1 1 calc R U . . .
C22 C 0.57729(18) 0.0399(5) -0.07260(12) 0.0728(7) Uani 1 1 d . . . . .
H22A H 0.5684 0.0908 -0.0340 0.109 Uiso 1 1 calc R U . . .
H22B H 0.6410 -0.0223 -0.0714 0.109 Uiso 1 1 calc R U . . .
H22C H 0.5303 -0.0748 -0.0855 0.109 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
N1 N2 1.253(2) . ?
N1 C6 1.431(2) . ?
O1 C10 1.349(2) . ?
O1 H1A 0.96(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
N2 C7 1.423(2) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
N3 C13 1.279(2) . ?
N3 C14 1.436(2) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C7 C12 1.381(2) . ?
C7 C8 1.401(3) . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(3) . ?
C11 C12 1.393(2) . ?
C11 C13 1.453(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.393(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.396(3) . ?
C15 C20 1.507(3) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 C21 1.518(3) . ?
C18 C19 1.391(3) . ?
C18 H18 0.9300 . ?
C19 C22 1.503(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 N1 C6 113.82(16) . . ?
C10 O1 H1A 108.6(17) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
N1 N2 C7 114.53(16) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C13 N3 C14 118.73(16) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.68(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.23(18) . . ?
C1 C6 N1 115.59(18) . . ?
C5 C6 N1 124.17(16) . . ?
C12 C7 C8 119.48(16) . . ?
C12 C7 N2 116.09(16) . . ?
C8 C7 N2 124.43(15) . . ?
C9 C8 C7 120.63(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.02(17) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
O1 C10 C9 118.55(17) . . ?
O1 C10 C11 121.25(16) . . ?
C9 C10 C11 120.20(16) . . ?
C12 C11 C10 118.66(15) . . ?
C12 C11 C13 119.70(16) . . ?
C10 C11 C13 121.63(16) . . ?
C7 C12 C11 120.98(17) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N3 C13 C11 122.02(18) . . ?
N3 C13 H13 119.0 . . ?
C11 C13 H13 119.0 . . ?
C19 C14 C15 121.26(17) . . ?
C19 C14 N3 117.72(18) . . ?
C15 C14 N3 120.97(18) . . ?
C14 C15 C16 117.8(2) . . ?
C14 C15 C20 123.06(19) . . ?
C16 C15 C20 119.1(2) . . ?
C17 C16 C15 122.2(2) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 118.34(19) . . ?
C16 C17 C21 121.1(2) . . ?
C18 C17 C21 120.6(2) . . ?
C17 C18 C19 122.2(2) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C14 118.1(2) . . ?
C18 C19 C22 120.7(2) . . ?
C14 C19 C22 121.15(18) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C7 179.33(15) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 N1 -179.24(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 N1 179.28(19) . . . . ?
N2 N1 C6 C1 177.55(17) . . . . ?
N2 N1 C6 C5 -1.9(3) . . . . ?
N1 N2 C7 C12 177.20(16) . . . . ?
N1 N2 C7 C8 -2.9(3) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
N2 C7 C8 C9 179.55(18) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 O1 179.04(18) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
O1 C10 C11 C12 -178.71(17) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
O1 C10 C11 C13 1.5(3) . . . . ?
C9 C10 C11 C13 -178.45(17) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
N2 C7 C12 C11 -179.19(16) . . . . ?
C10 C11 C12 C7 -1.3(3) . . . . ?
C13 C11 C12 C7 178.48(17) . . . . ?
C14 N3 C13 C11 179.14(17) . . . . ?
C12 C11 C13 N3 -178.29(17) . . . . ?
C10 C11 C13 N3 1.5(3) . . . . ?
C13 N3 C14 C19 111.7(2) . . . . ?
C13 N3 C14 C15 -70.6(2) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
N3 C14 C15 C16 -179.96(18) . . . . ?
C19 C14 C15 C20 175.9(2) . . . . ?
N3 C14 C15 C20 -1.7(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C20 C15 C16 C17 -178.2(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C15 C16 C17 C21 -178.1(2) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C21 C17 C18 C19 178.5(2) . . . . ?
C17 C18 C19 C14 -1.1(3) . . . . ?
C17 C18 C19 C22 -179.9(2) . . . . ?
C15 C14 C19 C18 2.9(3) . . . . ?
N3 C14 C19 C18 -179.51(18) . . . . ?
C15 C14 C19 C22 -178.3(2) . . . . ?
N3 C14 C19 C22 -0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N3 0.96(3) 1.76(3) 2.612(2) 146(2) .

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e6
_database_code_depnum_ccdc_archive 'CCDC 1578920'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O'
_chemical_formula_weight         315.36

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'

_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                   26.761(5)
_cell_length_b                   4.7207(7)
_cell_length_c                   12.577(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.880(6)
_cell_angle_gamma                90
_cell_volume                     1588.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5940
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.56

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27415
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.046
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3233
_reflns_number_gt                2080
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0509P)²+1.0812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0088(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3233
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.70505(6) 0.7857(4) 0.33111(12) 0.0490(5) Uani 1 1 d . . . . .
H1A H 0.6893 0.8981 0.3667 0.074 Uiso 1 1 calc R U . . .
N1 N 0.85838(7) -0.0362(4) 0.54510(16) 0.0420(5) Uani 1 1 d . . . . .
C1 C 0.92212(9) -0.3833(6) 0.5588(2) 0.0509(7) Uani 1 1 d . . . . .
H1 H 0.9254 -0.3613 0.4859 0.061 Uiso 1 1 calc R U . . .
N2 N 0.82704(7) 0.1125(4) 0.59262(15) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.95214(9) -0.5755(6) 0.6141(3) 0.0581(8) Uani 1 1 d . . . . .
H2 H 0.9758 -0.6804 0.5787 0.070 Uiso 1 1 calc R U . . .
N3 N 0.67158(6) 1.0135(4) 0.49986(14) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.94682(9) -0.6107(6) 0.7213(2) 0.0538(7) Uani 1 1 d . . . . .
H3 H 0.9670 -0.7395 0.7587 0.065 Uiso 1 1 calc R U . . .
C4 C 0.91166(9) -0.4553(6) 0.7735(2) 0.0526(7) Uani 1 1 d . . . . .
H4 H 0.9079 -0.4817 0.8461 0.063 Uiso 1 1 calc R U . . .
C5 C 0.88194(9) -0.2604(5) 0.7191(2) 0.0457(6) Uani 1 1 d . . . . .
H5 H 0.8585 -0.1547 0.7550 0.055 Uiso 1 1 calc R U . . .
C6 C 0.88725(8) -0.2238(5) 0.61119(19) 0.0382(6) Uani 1 1 d . . . . .
C7 C 0.79772(7) 0.2891(4) 0.52273(17) 0.0311(5) Uani 1 1 d . . . . .
C8 C 0.79855(8) 0.2726(5) 0.41184(18) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.8201 0.1462 0.3800 0.047 Uiso 1 1 calc R U . . .
C9 C 0.76783(8) 0.4410(5) 0.34957(18) 0.0408(6) Uani 1 1 d . . . . .
H9 H 0.7688 0.4279 0.2759 0.049 Uiso 1 1 calc R U . . .
C10 C 0.73526(8) 0.6310(5) 0.39540(17) 0.0339(5) Uani 1 1 d . . . . .
C11 C 0.73411(7) 0.6545(4) 0.50711(16) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.76574(7) 0.4806(4) 0.56830(17) 0.0316(5) Uani 1 1 d . . . . .
H12 H 0.7653 0.4938 0.6420 0.038 Uiso 1 1 calc R U . . .
C13 C 0.70089(8) 0.8533(4) 0.55625(17) 0.0308(5) Uani 1 1 d . . . . .
H13 H 0.7007 0.8657 0.6300 0.037 Uiso 1 1 calc R U . . .
C14 C 0.63885(7) 1.2135(4) 0.54463(17) 0.0306(5) Uani 1 1 d . . . . .
C15 C 0.63928(8) 1.2948(5) 0.65047(18) 0.0374(6) Uani 1 1 d . . . . .
H15 H 0.6624 1.2151 0.6985 0.045 Uiso 1 1 calc R U . . .
C16 C 0.60554(8) 1.4935(5) 0.68537(18) 0.0391(6) Uani 1 1 d . . . . .
H16 H 0.6065 1.5448 0.7568 0.047 Uiso 1 1 calc R U . . .
C17 C 0.57041(8) 1.6180(5) 0.61695(18) 0.0350(5) Uani 1 1 d . . . . .
C18 C 0.57093(9) 1.5404(5) 0.51117(19) 0.0414(6) Uani 1 1 d . . . . .
H18 H 0.5481 1.6223 0.4629 0.050 Uiso 1 1 calc R U . . .
C19 C 0.60470(8) 1.3433(5) 0.47580(18) 0.0390(6) Uani 1 1 d . . . . .
H19 H 0.6044 1.2969 0.4039 0.047 Uiso 1 1 calc R U . . .
C20 C 0.53354(9) 1.8305(5) 0.6569(2) 0.0478(6) Uani 1 1 d . . . . .
H20A H 0.5002 1.7598 0.6451 0.072 Uiso 1 1 calc R U . . .
H20B H 0.5372 2.0060 0.6193 0.072 Uiso 1 1 calc R U . . .
H20C H 0.5397 1.8613 0.7316 0.072 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
O1 C10 1.341(3) . ?
O1 H1A 0.8200 . ?
N1 N2 1.259(3) . ?
N1 C6 1.425(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.384(4) . ?
C1 H1 0.9300 . ?
N2 C7 1.428(3) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
N3 C13 1.286(3) . ?
N3 C14 1.417(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C7 C12 1.382(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.411(3) . ?
C11 C12 1.393(3) . ?
C11 C13 1.445(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.382(3) . ?
C14 C15 1.385(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 C20 1.505(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C10 O1 H1A 109.5 . . ?
N2 N1 C6 115.2(2) . . ?
C6 C1 C2 120.5(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
N1 N2 C7 113.23(19) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C13 N3 C14 123.12(19) . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 N1 125.5(2) . . ?
C1 C6 N1 115.0(2) . . ?
C12 C7 C8 118.7(2) . . ?
C12 C7 N2 117.5(2) . . ?
C8 C7 N2 123.7(2) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O1 C10 C9 118.4(2) . . ?
O1 C10 C11 121.7(2) . . ?
C9 C10 C11 119.9(2) . . ?
C12 C11 C10 118.10(19) . . ?
C12 C11 C13 121.18(19) . . ?
C10 C11 C13 120.72(19) . . ?
C7 C12 C11 122.0(2) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N3 C13 C11 121.2(2) . . ?
N3 C13 H13 119.4 . . ?
C11 C13 H13 119.4 . . ?
C19 C14 C15 117.6(2) . . ?
C19 C14 N3 116.84(19) . . ?
C15 C14 N3 125.5(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 117.3(2) . . ?
C18 C17 C20 121.7(2) . . ?
C16 C17 C20 121.0(2) . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 C7 -177.78(17) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 N1 178.4(2) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 N1 -179.4(2) . . . . ?
N2 N1 C6 C5 2.7(3) . . . . ?
N2 N1 C6 C1 -179.1(2) . . . . ?
N1 N2 C7 C12 -173.74(19) . . . . ?
N1 N2 C7 C8 8.3(3) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
N2 C7 C8 C9 177.2(2) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 O1 -178.3(2) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
O1 C10 C11 C12 178.3(2) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
O1 C10 C11 C13 -1.6(3) . . . . ?
C9 C10 C11 C13 179.3(2) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
N2 C7 C12 C11 -177.39(18) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C13 C11 C12 C7 179.95(19) . . . . ?
C14 N3 C13 C11 -179.25(18) . . . . ?
C12 C11 C13 N3 -179.82(19) . . . . ?
C10 C11 C13 N3 0.0(3) . . . . ?
C13 N3 C14 C19 -171.4(2) . . . . ?
C13 N3 C14 C15 10.6(3) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
N3 C14 C15 C16 179.8(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C15 C16 C17 C20 179.1(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C20 C17 C18 C19 -179.5(2) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C15 C14 C19 C18 -2.1(3) . . . . ?
N3 C14 C19 C18 179.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N3 0.82 1.84 2.567(2) 147.4 .
C13 H13 O1 0.93 2.63 3.517(3) 160.4 4_576

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_e10
_database_code_depnum_ccdc_archive 'CCDC 1578921'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2018-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 Cl N3 O2 Ru'
_chemical_formula_weight         601.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5213(12)
_cell_length_b                   11.9176(15)
_cell_length_c                   12.2605(16)
_cell_angle_alpha                61.411(4)
_cell_angle_beta                 85.811(4)
_cell_angle_gamma                88.731(4)
_cell_volume                     1346.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.35

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6310
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65375
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6706
_reflns_number_gt                5994
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0241P)²+1.2407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6706
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.24458(2) 0.53620(2) 0.20722(2) 0.02606(5) Uani 1 1 d . . . . .
N3 N 0.31560(16) 0.71600(16) 0.16625(15) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.18770(14) 0.50964(13) 0.38240(13) 0.0314(3) Uani 1 1 d . . . . .
Cl1 Cl 0.04443(5) 0.64501(5) 0.14209(5) 0.03625(11) Uani 1 1 d . . . . .
C21 C 0.2569(2) 0.4876(2) 0.0537(2) 0.0409(5) Uani 1 1 d . . . . .
C22 C 0.1845(2) 0.3927(2) 0.1585(2) 0.0398(5) Uani 1 1 d . . . . .
H22 H 0.1031 0.3717 0.1486 0.048 Uiso 1 1 calc R U . . .
C23 C 0.2324(2) 0.3302(2) 0.2762(2) 0.0373(5) Uani 1 1 d . . . . .
H23 H 0.1834 0.2668 0.3424 0.045 Uiso 1 1 calc R U . . .
C24 C 0.3551(2) 0.3620(2) 0.2962(2) 0.0360(5) Uani 1 1 d . . . . .
C25 C 0.4278(2) 0.4560(2) 0.1930(2) 0.0382(5) Uani 1 1 d . . . . .
H25 H 0.5088 0.4777 0.2031 0.046 Uiso 1 1 calc R U . . .
C26 C 0.3786(2) 0.5180(2) 0.0735(2) 0.0397(5) Uani 1 1 d . . . . .
H26 H 0.4280 0.5803 0.0067 0.048 Uiso 1 1 calc R U . . .
C1 C 0.0065(3) 0.8859(3) 0.8153(2) 0.0465(6) Uani 1 1 d . . . . .
H1 H -0.0220 0.8022 0.8664 0.056 Uiso 1 1 calc R U . . .
N1 N 0.08008(19) 0.82123(18) 0.66503(17) 0.0364(4) Uani 1 1 d . . . . .
O2 O 0.57173(18) 0.7271(2) 0.1669(2) 0.0664(6) Uani 1 1 d . . . . .
C2 C -0.0117(3) 0.9767(3) 0.8553(3) 0.0543(7) Uani 1 1 d . . . . .
H2 H -0.0513 0.9533 0.9336 0.065 Uiso 1 1 calc R U . . .
N2 N 0.14842(18) 0.85318(18) 0.56646(17) 0.0370(4) Uani 1 1 d . . . . .
C3 C 0.0285(3) 1.0999(3) 0.7799(3) 0.0537(7) Uani 1 1 d . . . . .
H3 H 0.0160 1.1604 0.8070 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0874(3) 1.1350(3) 0.6638(3) 0.0556(7) Uani 1 1 d . . . . .
H4 H 0.1141 1.2192 0.6127 0.067 Uiso 1 1 calc R U . . .
C5 C 0.1070(3) 1.0456(2) 0.6227(2) 0.0460(6) Uani 1 1 d . . . . .
H5 H 0.1468 1.0696 0.5443 0.055 Uiso 1 1 calc R U . . .
C6 C 0.0668(2) 0.9201(2) 0.6996(2) 0.0353(4) Uani 1 1 d . . . . .
C7 C 0.1603(2) 0.7594(2) 0.5270(2) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.1142(2) 0.6324(2) 0.59548(19) 0.0326(4) Uani 1 1 d . . . . .
H8 H 0.0750 0.6037 0.6749 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1269(2) 0.55142(20) 0.54590(18) 0.0308(4) Uani 1 1 d . . . . .
H9 H 0.0976 0.4675 0.5934 0.037 Uiso 1 1 calc R U . . .
C10 C 0.18369(17) 0.59165(18) 0.42355(18) 0.0260(4) Uani 1 1 d . . . . .
C11 C 0.23255(19) 0.71908(19) 0.35585(18) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.2205(2) 0.7994(2) 0.4105(2) 0.0340(4) Uani 1 1 d . . . . .
H12 H 0.2542 0.8821 0.3667 0.041 Uiso 1 1 calc R U . . .
C13 C 0.29972(19) 0.77000(19) 0.23581(19) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.3360 0.8510 0.2043 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3922(2) 0.7858(2) 0.0514(2) 0.0339(4) Uani 1 1 d . . . . .
C15 C 0.3343(3) 0.8435(3) -0.0593(2) 0.0510(6) Uani 1 1 d . . . . .
H15 H 0.2459 0.8430 -0.0591 0.061 Uiso 1 1 calc R U . . .
C16 C 0.4081(4) 0.9024(3) -0.1712(3) 0.0747(10) Uani 1 1 d . . . . .
H16 H 0.3694 0.9420 -0.2461 0.090 Uiso 1 1 calc R U . . .
C17 C 0.5371(4) 0.9022(4) -0.1709(3) 0.0804(12) Uani 1 1 d . . . . .
H17 H 0.5860 0.9404 -0.2464 0.096 Uiso 1 1 calc R U . . .
C18 C 0.5967(3) 0.8470(3) -0.0620(3) 0.0682(9) Uani 1 1 d . . . . .
H18 H 0.6852 0.8489 -0.0638 0.082 Uiso 1 1 calc R U . . .
C19 C 0.5244(2) 0.7878(3) 0.0523(2) 0.0453(6) Uani 1 1 d . . . . .
C20 C 0.7040(3) 0.7394(5) 0.1751(5) 0.1090(16) Uani 1 1 d . . . . .
H20A H 0.7516 0.7084 0.1253 0.163 Uiso 1 1 calc R U . . .
H20B H 0.7244 0.6904 0.2603 0.163 Uiso 1 1 calc R U . . .
H20C H 0.7254 0.8277 0.1452 0.163 Uiso 1 1 calc R U . . .
C27 C 0.2035(3) 0.5573(3) -0.0717(3) 0.0670(9) Uani 1 1 d . . . . .
H27A H 0.1209 0.5892 -0.0633 0.101 Uiso 1 1 calc R U . . .
H27B H 0.1963 0.4999 -0.1054 0.101 Uiso 1 1 calc R U . . .
H27C H 0.2593 0.6274 -0.1267 0.101 Uiso 1 1 calc R U . . .
C28 C 0.3994(3) 0.2976(3) 0.4266(3) 0.0552(7) Uani 1 1 d . . . . .
H28 H 0.3235 0.2791 0.4841 0.066 Uiso 1 1 calc R U . . .
C29 C 0.4882(4) 0.3794(4) 0.4517(4) 0.0856(12) Uani 1 1 d . . . . .
H29A H 0.5671 0.3927 0.4023 0.128 Uiso 1 1 calc R U . . .
H29B H 0.5043 0.3370 0.5383 0.128 Uiso 1 1 calc R U . . .
H29C H 0.4495 0.4603 0.4303 0.128 Uiso 1 1 calc R U . . .
C30 C 0.4592(4) 0.1693(3) 0.4538(3) 0.0821(11) Uani 1 1 d . . . . .
H31A H 0.3984 0.1174 0.4427 0.123 Uiso 1 1 calc R U . . .
H31B H 0.4835 0.1263 0.5380 0.123 Uiso 1 1 calc R U . . .
H31C H 0.5331 0.1838 0.3977 0.123 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 O1 2.0594(14) . ?
Ru1 N3 2.0948(17) . ?
Ru1 C25 2.165(2) . ?
Ru1 C26 2.171(2) . ?
Ru1 C22 2.182(2) . ?
Ru1 C24 2.183(2) . ?
Ru1 C23 2.184(2) . ?
Ru1 C21 2.214(2) . ?
Ru1 Cl1 2.4264(6) . ?
N3 C13 1.292(3) . ?
N3 C14 1.438(2) . ?
O1 C10 1.296(2) . ?
C21 C26 1.406(3) . ?
C21 C22 1.420(4) . ?
C21 C27 1.501(4) . ?
C22 C23 1.397(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.425(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.407(3) . ?
C24 C28 1.510(3) . ?
C25 C26 1.421(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C1 C6 1.382(3) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9300 . ?
N1 N2 1.252(3) . ?
N1 C6 1.431(3) . ?
O2 C19 1.364(3) . ?
O2 C20 1.418(4) . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
N2 C7 1.415(3) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C7 C12 1.378(3) . ?
C7 C8 1.410(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.425(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.423(3) . ?
C11 C12 1.406(3) . ?
C11 C13 1.430(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.376(3) . ?
C14 C19 1.393(3) . ?
C15 C16 1.387(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(4) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.512(5) . ?
C28 C30 1.531(4) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H31A 0.9600 . ?
C30 H31B 0.9600 . ?
C30 H31C 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
O1 Ru1 N3 87.61(6) . . ?
O1 Ru1 C25 114.82(8) . . ?
N3 Ru1 C25 95.99(8) . . ?
O1 Ru1 C26 153.07(8) . . ?
N3 Ru1 C26 93.71(8) . . ?
C25 Ru1 C26 38.27(9) . . ?
O1 Ru1 C22 117.52(8) . . ?
N3 Ru1 C22 153.92(8) . . ?
C25 Ru1 C22 80.26(9) . . ?
C26 Ru1 C22 67.32(9) . . ?
O1 Ru1 C24 87.96(7) . . ?
N3 Ru1 C24 122.73(8) . . ?
C25 Ru1 C24 37.77(9) . . ?
C26 Ru1 C24 68.74(9) . . ?
C22 Ru1 C24 68.48(9) . . ?
O1 Ru1 C23 90.07(7) . . ?
N3 Ru1 C23 160.78(8) . . ?
C25 Ru1 C23 67.78(9) . . ?
C26 Ru1 C23 79.92(9) . . ?
C22 Ru1 C23 37.32(9) . . ?
C24 Ru1 C23 38.08(9) . . ?
O1 Ru1 C21 155.19(8) . . ?
N3 Ru1 C21 116.94(8) . . ?
C25 Ru1 C21 68.62(9) . . ?
C26 Ru1 C21 37.40(9) . . ?
C22 Ru1 C21 37.67(9) . . ?
C24 Ru1 C21 81.70(8) . . ?
C23 Ru1 C21 67.99(9) . . ?
O1 Ru1 Cl1 86.67(4) . . ?
N3 Ru1 Cl1 85.14(5) . . ?
C25 Ru1 Cl1 158.50(7) . . ?
C26 Ru1 Cl1 120.25(7) . . ?
C22 Ru1 Cl1 89.30(6) . . ?
C24 Ru1 Cl1 151.35(6) . . ?
C23 Ru1 Cl1 113.78(6) . . ?
C21 Ru1 Cl1 91.66(6) . . ?
C13 N3 C14 116.16(17) . . ?
C13 N3 Ru1 126.27(13) . . ?
C14 N3 Ru1 117.55(13) . . ?
C10 O1 Ru1 129.20(13) . . ?
C26 C21 C22 117.3(2) . . ?
C26 C21 C27 121.3(3) . . ?
C22 C21 C27 121.4(3) . . ?
C26 C21 Ru1 69.64(12) . . ?
C22 C21 Ru1 69.96(12) . . ?
C27 C21 Ru1 128.98(17) . . ?
C23 C22 C21 121.6(2) . . ?
C23 C22 Ru1 71.42(12) . . ?
C21 C22 Ru1 72.36(12) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
Ru1 C22 H22 129.6 . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 Ru1 71.26(13) . . ?
C24 C23 Ru1 70.91(12) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
Ru1 C23 H23 131.2 . . ?
C25 C24 C23 117.8(2) . . ?
C25 C24 C28 123.1(2) . . ?
C23 C24 C28 119.1(2) . . ?
C25 C24 Ru1 70.44(12) . . ?
C23 C24 Ru1 71.01(12) . . ?
C28 C24 Ru1 127.85(16) . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 Ru1 71.79(12) . . ?
C26 C25 Ru1 71.07(12) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
Ru1 C25 H25 130.0 . . ?
C21 C26 C25 121.6(2) . . ?
C21 C26 Ru1 72.95(12) . . ?
C25 C26 Ru1 70.66(12) . . ?
C21 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
Ru1 C26 H26 129.8 . . ?
C6 C1 C2 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
N2 N1 C6 113.53(18) . . ?
C19 O2 C20 118.3(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N1 N2 C7 115.19(18) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 N1 116.3(2) . . ?
C5 C6 N1 123.8(2) . . ?
C12 C7 C8 118.91(18) . . ?
C12 C7 N2 115.55(19) . . ?
C8 C7 N2 125.53(19) . . ?
C9 C8 C7 120.41(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.96(19) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
O1 C10 C11 124.85(17) . . ?
O1 C10 C9 117.77(17) . . ?
C11 C10 C9 117.38(17) . . ?
C12 C11 C10 119.29(18) . . ?
C12 C11 C13 116.98(18) . . ?
C10 C11 C13 123.67(17) . . ?
C7 C12 C11 121.96(19) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N3 C13 C11 127.24(18) . . ?
N3 C13 H13 116.4 . . ?
C11 C13 H13 116.4 . . ?
C15 C14 C19 120.6(2) . . ?
C15 C14 N3 119.4(2) . . ?
C19 C14 N3 119.9(2) . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
O2 C19 C14 115.7(2) . . ?
O2 C19 C18 125.8(3) . . ?
C14 C19 C18 118.4(3) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 C29 113.9(3) . . ?
C24 C28 C30 109.3(2) . . ?
C29 C28 C30 111.6(3) . . ?
C24 C28 H28 107.2 . . ?
C29 C28 H28 107.2 . . ?
C30 C28 H28 107.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H31A 109.5 . . ?
C28 C30 H31B 109.5 . . ?
H31A C30 H31B 109.5 . . ?
C28 C30 H31C 109.5 . . ?
H31A C30 H31C 109.5 . . ?
H31B C30 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C26 C21 C22 C23 -1.1(3) . . . . ?
C27 C21 C22 C23 -178.1(2) . . . . ?
Ru1 C21 C22 C23 -53.95(18) . . . . ?
C26 C21 C22 Ru1 52.82(17) . . . . ?
C27 C21 C22 Ru1 -124.2(2) . . . . ?
C21 C22 C23 C24 1.7(3) . . . . ?
Ru1 C22 C23 C24 -52.63(18) . . . . ?
C21 C22 C23 Ru1 54.37(18) . . . . ?
C22 C23 C24 C25 -1.6(3) . . . . ?
Ru1 C23 C24 C25 -54.41(17) . . . . ?
C22 C23 C24 C28 176.2(2) . . . . ?
Ru1 C23 C24 C28 123.5(2) . . . . ?
C22 C23 C24 Ru1 52.79(18) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
C28 C24 C25 C26 -176.8(2) . . . . ?
Ru1 C24 C25 C26 -53.72(18) . . . . ?
C23 C24 C25 Ru1 54.69(17) . . . . ?
C28 C24 C25 Ru1 -123.1(2) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C27 C21 C26 C25 177.5(2) . . . . ?
Ru1 C21 C26 C25 53.45(18) . . . . ?
C22 C21 C26 Ru1 -52.97(17) . . . . ?
C27 C21 C26 Ru1 124.0(2) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
Ru1 C25 C26 C21 -54.49(19) . . . . ?
C24 C25 C26 Ru1 54.05(18) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 N1 N2 C7 -177.95(18) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C1 C6 N1 -179.2(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 N1 178.6(2) . . . . ?
N2 N1 C6 C1 -171.9(2) . . . . ?
N2 N1 C6 C5 10.2(3) . . . . ?
N1 N2 C7 C12 171.5(2) . . . . ?
N1 N2 C7 C8 -7.4(3) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
N2 C7 C8 C9 177.5(2) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
Ru1 O1 C10 C11 -7.2(3) . . . . ?
Ru1 O1 C10 C9 173.22(14) . . . . ?
C8 C9 C10 O1 -177.61(19) . . . . ?
C8 C9 C10 C11 2.7(3) . . . . ?
O1 C10 C11 C12 179.04(19) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
O1 C10 C11 C13 -4.0(3) . . . . ?
C9 C10 C11 C13 175.58(19) . . . . ?
C8 C7 C12 C11 2.7(3) . . . . ?
N2 C7 C12 C11 -176.2(2) . . . . ?
C10 C11 C12 C7 -1.4(3) . . . . ?
C13 C11 C12 C7 -178.5(2) . . . . ?
C14 N3 C13 C11 -177.4(2) . . . . ?
Ru1 N3 C13 C11 1.0(3) . . . . ?
C12 C11 C13 N3 -175.8(2) . . . . ?
C10 C11 C13 N3 7.2(3) . . . . ?
C13 N3 C14 C15 -106.6(3) . . . . ?
Ru1 N3 C14 C15 74.9(2) . . . . ?
C13 N3 C14 C19 77.3(3) . . . . ?
Ru1 N3 C14 C19 -101.2(2) . . . . ?
C19 C14 C15 C16 1.1(4) . . . . ?
N3 C14 C15 C16 -174.9(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C17 C18 C19 0.8(6) . . . . ?
C20 O2 C19 C14 -172.2(3) . . . . ?
C20 O2 C19 C18 9.9(5) . . . . ?
C15 C14 C19 O2 -179.6(2) . . . . ?
N3 C14 C19 O2 -3.6(3) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
N3 C14 C19 C18 174.4(2) . . . . ?
C17 C18 C19 O2 178.4(3) . . . . ?
C17 C18 C19 C14 0.6(5) . . . . ?
C25 C24 C28 C29 28.5(4) . . . . ?
C23 C24 C28 C29 -149.3(3) . . . . ?
Ru1 C24 C28 C29 -61.5(3) . . . . ?
C25 C24 C28 C30 -97.1(3) . . . . ?
C23 C24 C28 C30 85.2(3) . . . . ?
Ru1 C24 C28 C30 172.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Cl1 0.93 2.96 3.654(2) 132.2 2_566
C3 H3 Cl1 0.93 2.73 3.649(2) 171.3 2_576

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

