# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_bc1brbh
_database_code_depnum_ccdc_archive 'CCDC 1872211'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2018-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 Br Cl N3 O Ru'
_chemical_formula_sum            'C25 H21 Br Cl N3 O Ru'
_chemical_formula_weight         595.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br1 C25 Cl1 H20 N3 O1 Ru1'
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6369(7)
_cell_length_b                   12.9702(7)
_cell_length_c                   15.9325(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.950(6)
_cell_angle_gamma                90
_cell_volume                     2260.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4764
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.8830
_cell_measurement_theta_min      4.3760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15286
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.433
_diffrn_reflns_theta_min         3.423
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  86.00   1.00    2.92    --    9.75  77.00 120.00  109
  2  ω    -45.00  64.00   1.00    2.92    --  -11.93  77.00-120.00  109
  3  ω   -100.00 -65.00   1.00    2.92    --  -11.93-179.00 -30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0315069000
_diffrn_orient_matrix_UB_12      0.0447113000
_diffrn_orient_matrix_UB_13      0.0215813000
_diffrn_orient_matrix_UB_21      -0.0336449000
_diffrn_orient_matrix_UB_22      0.0303099000
_diffrn_orient_matrix_UB_23      -0.0373702000
_diffrn_orient_matrix_UB_31      -0.0455566000
_diffrn_orient_matrix_UB_32      0.0085585000
_diffrn_orient_matrix_UB_33      0.0195533000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4411
_reflns_number_total             5510
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.6319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.35162(2) 0.62526(2) 0.30929(2) 0.02672(7) Uani 1 1 d . . . . .
Br1 Br 0.22010(3) 0.42660(2) -0.24504(2) 0.04783(10) Uani 1 1 d . . . . .
Cl1 Cl 0.28928(7) 0.46675(5) 0.36078(5) 0.03988(17) Uani 1 1 d . . . . .
O1 O 0.34369(16) 0.54505(14) 0.19563(11) 0.0341(4) Uani 1 1 d . . . . .
N1 N 0.17219(19) 0.64706(16) 0.22426(13) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.1546(2) 0.62265(16) 0.13501(13) 0.0291(5) Uani 1 1 d . . . . .
N3 N 0.1186(2) 0.6450(2) 0.39490(15) 0.0345(5) Uani 1 1 d . . . . .
H3 H 0.161(3) 0.604(2) 0.398(2) 0.036(9) Uiso 1 1 d . . . . .
C1 C 0.2458(2) 0.56799(19) 0.12944(16) 0.0281(5) Uani 1 1 d . . . . .
C2 C 0.2371(2) 0.52959(19) 0.03942(16) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.1353(3) 0.5508(2) -0.03498(18) 0.0370(6) Uani 1 1 d . . . . .
H3A H 0.069752 0.586333 -0.028036 0.044 Uiso 1 1 calc R . . . .
C4 C 0.1299(3) 0.5199(2) -0.11913(18) 0.0402(7) Uani 1 1 d . . . . .
H4 H 0.061372 0.534176 -0.168733 0.048 Uiso 1 1 calc R . . . .
C5 C 0.2283(3) 0.4673(2) -0.12831(17) 0.0333(6) Uani 1 1 d . . . . .
C6 C 0.3286(3) 0.4426(2) -0.05583(19) 0.0409(7) Uani 1 1 d . . . . .
H6 H 0.392850 0.405189 -0.062948 0.049 Uiso 1 1 calc R . . . .
C7 C 0.3328(3) 0.4742(2) 0.02797(18) 0.0378(6) Uani 1 1 d . . . . .
H7 H 0.400679 0.458077 0.077468 0.045 Uiso 1 1 calc R . . . .
C8 C 0.0831(2) 0.69930(19) 0.23626(16) 0.0267(5) Uani 1 1 d . . . . .
C9 C -0.0136(2) 0.7517(2) 0.16025(17) 0.0310(6) Uani 1 1 d . . . . .
H9A H -0.083511 0.706279 0.136952 0.037 Uiso 1 1 calc R . . . .
H9B H 0.018402 0.765677 0.112594 0.037 Uiso 1 1 calc R . . . .
C10 C -0.0541(3) 0.8528(2) 0.1910(2) 0.0400(7) Uani 1 1 d . . . . .
H10A H 0.014654 0.899978 0.209254 0.048 Uiso 1 1 calc R . . . .
H10B H -0.117592 0.883801 0.140919 0.048 Uiso 1 1 calc R . . . .
C11 C -0.1022(3) 0.8394(2) 0.26776(19) 0.0385(6) Uani 1 1 d . . . . .
H11A H -0.103920 0.905762 0.295455 0.046 Uiso 1 1 calc R . . . .
H11B H -0.185085 0.812901 0.245234 0.046 Uiso 1 1 calc R . . . .
C12 C -0.0230(2) 0.76689(19) 0.33531(17) 0.0290(5) Uani 1 1 d . . . . .
C13 C -0.0296(2) 0.7378(2) 0.41955(17) 0.0319(6) Uani 1 1 d . . . . .
C14 C -0.1076(3) 0.7650(2) 0.4667(2) 0.0454(7) Uani 1 1 d . . . . .
H14 H -0.168104 0.814540 0.444171 0.054 Uiso 1 1 calc R . . . .
C15 C -0.0931(4) 0.7174(3) 0.5463(2) 0.0588(9) Uani 1 1 d . . . . .
H15 H -0.144507 0.734762 0.577814 0.071 Uiso 1 1 calc R . . . .
C16 C -0.0019(4) 0.6430(3) 0.5812(2) 0.0603(10) Uani 1 1 d . . . . .
H16 H 0.006458 0.612492 0.635845 0.072 Uiso 1 1 calc R . . . .
C17 C 0.0758(3) 0.6138(2) 0.53672(19) 0.0465(8) Uani 1 1 d . . . . .
H17 H 0.136456 0.564617 0.560228 0.056 Uiso 1 1 calc R . . . .
C18 C 0.0593(2) 0.6611(2) 0.45497(17) 0.0331(6) Uani 1 1 d . . . . .
C19 C 0.0665(2) 0.70773(19) 0.32171(16) 0.0273(5) Uani 1 1 d . . . . .
C20 C 0.4149(3) 0.7776(3) 0.2901(2) 0.0522(8) Uani 1 1 d . . . . .
H20 H 0.390532 0.821096 0.240763 0.063 Uiso 1 1 calc R . . . .
C21 C 0.3583(3) 0.7830(2) 0.3528(2) 0.0529(9) Uani 1 1 d . . . . .
H21 H 0.294058 0.829014 0.344345 0.063 Uiso 1 1 calc R . . . .
C22 C 0.3948(3) 0.7217(3) 0.4280(2) 0.0582(10) Uani 1 1 d . . . . .
H22 H 0.356546 0.727110 0.470424 0.070 Uiso 1 1 calc R . . . .
C23 C 0.4910(4) 0.6506(3) 0.4398(2) 0.0694(13) Uani 1 1 d . . . . .
H23 H 0.515976 0.608188 0.489841 0.083 Uiso 1 1 calc R . . . .
C24 C 0.5494(3) 0.6441(3) 0.3749(3) 0.0635(11) Uani 1 1 d . . . . .
H24 H 0.613849 0.598714 0.381862 0.076 Uiso 1 1 calc R . . . .
C25 C 0.5067(3) 0.7084(3) 0.3004(2) 0.0570(9) Uani 1 1 d . . . . .
H25 H 0.542125 0.703818 0.256244 0.068 Uiso 1 1 calc R . . . .


_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 Cl1 2.4151(7) . ?
Ru1 O1 2.0632(17) . ?
Ru1 N1 2.084(2) . ?
Ru1 C20 2.166(3) . ?
Ru1 C21 2.153(3) . ?
Ru1 C22 2.179(3) . ?
Ru1 C23 2.182(3) . ?
Ru1 C24 2.193(3) . ?
Ru1 C25 2.149(3) . ?
Br1 C5 1.904(2) . ?
O1 C1 1.296(3) . ?
N1 N2 1.402(3) . ?
N1 C8 1.306(3) . ?
N2 C1 1.304(3) . ?
N3 H3 0.72(3) . ?
N3 C18 1.374(3) . ?
N3 C19 1.381(3) . ?
C1 C2 1.489(3) . ?
C2 C3 1.387(4) . ?
C2 C7 1.389(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 C6 1.371(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.505(3) . ?
C8 C19 1.443(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.530(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.519(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.489(4) . ?
C12 C13 1.421(4) . ?
C12 C19 1.369(3) . ?
C13 C14 1.407(4) . ?
C13 C18 1.407(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.402(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(5) . ?
C20 C25 1.362(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.413(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.420(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.397(5) . ?
C25 H25 0.9300 . ?

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 Cl1 86.57(6) . . ?
O1 Ru1 N1 76.29(7) . . ?
O1 Ru1 C20 104.58(11) . . ?
O1 Ru1 C21 138.38(12) . . ?
O1 Ru1 C22 168.41(10) . . ?
O1 Ru1 C23 135.11(15) . . ?
O1 Ru1 C24 101.55(12) . . ?
O1 Ru1 C25 88.96(11) . . ?
N1 Ru1 Cl1 89.19(6) . . ?
N1 Ru1 C20 95.62(11) . . ?
N1 Ru1 C21 89.92(10) . . ?
N1 Ru1 C22 111.69(12) . . ?
N1 Ru1 C23 148.55(15) . . ?
N1 Ru1 C24 161.89(13) . . ?
N1 Ru1 C25 124.52(12) . . ?
C20 Ru1 Cl1 168.61(9) . . ?
C20 Ru1 C22 67.04(13) . . ?
C20 Ru1 C23 79.58(13) . . ?
C20 Ru1 C24 67.27(14) . . ?
C21 Ru1 Cl1 132.99(11) . . ?
C21 Ru1 C20 37.04(13) . . ?
C21 Ru1 C22 37.12(14) . . ?
C21 Ru1 C23 67.45(14) . . ?
C21 Ru1 C24 79.83(13) . . ?
C22 Ru1 Cl1 101.59(10) . . ?
C22 Ru1 C23 37.81(15) . . ?
C22 Ru1 C24 68.18(14) . . ?
C23 Ru1 Cl1 90.94(10) . . ?
C23 Ru1 C24 37.88(16) . . ?
C24 Ru1 Cl1 108.73(11) . . ?
C25 Ru1 Cl1 143.74(11) . . ?
C25 Ru1 C20 36.80(13) . . ?
C25 Ru1 C21 66.75(14) . . ?
C25 Ru1 C22 79.59(13) . . ?
C25 Ru1 C23 67.63(15) . . ?
C25 Ru1 C24 37.51(15) . . ?
C1 O1 Ru1 111.22(15) . . ?
N2 N1 Ru1 113.33(15) . . ?
C8 N1 Ru1 130.12(17) . . ?
C8 N1 N2 114.6(2) . . ?
C1 N2 N1 110.6(2) . . ?
C18 N3 H3 125(3) . . ?
C18 N3 C19 108.5(2) . . ?
C19 N3 H3 126(3) . . ?
O1 C1 N2 125.4(2) . . ?
O1 C1 C2 117.3(2) . . ?
N2 C1 C2 117.3(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 C7 118.6(2) . . ?
C7 C2 C1 120.4(2) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Br1 118.2(2) . . ?
C6 C5 Br1 120.2(2) . . ?
C6 C5 C4 121.6(2) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.9(3) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
N1 C8 C9 122.0(2) . . ?
N1 C8 C19 123.1(2) . . ?
C19 C8 C9 114.9(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 C10 110.9(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.5(2) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.3(2) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C13 C12 C11 129.1(2) . . ?
C19 C12 C11 123.8(2) . . ?
C19 C12 C13 106.9(2) . . ?
C14 C13 C12 133.7(3) . . ?
C14 C13 C18 118.9(3) . . ?
C18 C13 C12 107.3(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 121.5 . . ?
C16 C17 C18 117.0(3) . . ?
C18 C17 H17 121.5 . . ?
N3 C18 C13 107.7(2) . . ?
N3 C18 C17 130.0(3) . . ?
C17 C18 C13 122.3(2) . . ?
N3 C19 C8 126.2(2) . . ?
C12 C19 N3 109.6(2) . . ?
C12 C19 C8 123.1(2) . . ?
Ru1 C20 H20 130.7 . . ?
C21 C20 Ru1 70.96(19) . . ?
C21 C20 H20 120.1 . . ?
C25 C20 Ru1 70.89(19) . . ?
C25 C20 H20 120.1 . . ?
C25 C20 C21 119.9(3) . . ?
Ru1 C21 H21 128.6 . . ?
C20 C21 Ru1 72.00(19) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.4(3) . . ?
C22 C21 Ru1 72.45(19) . . ?
C22 C21 H21 119.3 . . ?
Ru1 C22 H22 130.4 . . ?
C21 C22 Ru1 70.43(18) . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.1(3) . . ?
C23 C22 Ru1 71.22(19) . . ?
C23 C22 H22 120.4 . . ?
Ru1 C23 H23 129.9 . . ?
C22 C23 Ru1 70.97(18) . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(3) . . ?
C24 C23 Ru1 71.49(18) . . ?
C24 C23 H23 120.1 . . ?
Ru1 C24 H24 131.2 . . ?
C23 C24 Ru1 70.63(19) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 Ru1 69.51(19) . . ?
C25 C24 C23 117.6(3) . . ?
C25 C24 H24 121.2 . . ?
Ru1 C25 H25 128.1 . . ?
C20 C25 Ru1 72.31(19) . . ?
C20 C25 C24 122.1(3) . . ?
C20 C25 H25 118.9 . . ?
C24 C25 Ru1 73.0(2) . . ?
C24 C25 H25 118.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.896
_oxdiff_exptl_absorpt_empirical_full_min 0.803
####################################################################### 
# 
# 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_bc1bh
_database_code_depnum_ccdc_archive 'CCDC 1916478'
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 Cl N3 O Ru'
_chemical_formula_sum            'C25 H22 Cl N3 O Ru'
_chemical_formula_weight         516.97
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 Cl1 H25 N3 O1 Ru1'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   9.5226(3)
_cell_length_b                   12.4404(5)
_cell_length_c                   18.1571(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2150.96(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9940
_cell_measurement_theta_min      3.9810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12111
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.431
_diffrn_reflns_theta_min         3.462
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -54.00   1.00    2.69    --    9.75-179.00 150.00   25
  2  ω    -13.00  59.00   1.00    2.69    --  -11.78  38.00 -30.00   72
  3  ω    -82.00  26.00   1.00    2.69    --  -11.78 -19.00 150.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0511607000
_diffrn_orient_matrix_UB_12      -0.0334382000
_diffrn_orient_matrix_UB_13      -0.0167807000
_diffrn_orient_matrix_UB_21      0.0357494000
_diffrn_orient_matrix_UB_22      0.0461480000
_diffrn_orient_matrix_UB_23      -0.0132202000
_diffrn_orient_matrix_UB_31      0.0406515000
_diffrn_orient_matrix_UB_32      0.0015009000
_diffrn_orient_matrix_UB_33      0.0327128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                4604
_reflns_number_total             5159
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+0.2801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Others
 Sof(H9AA)=Sof(H9AB)=Sof(H11A)=Sof(H11B)=Sof(C10)=Sof(H10A)=Sof(H10B)=1-FVAR(1)
 Sof(H9BC)=Sof(H9BD)=Sof(H11C)=Sof(H11D)=Sof(C10A)=Sof(H10C)=Sof(H10D)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C11(H11A,H11B), C11(H11C,H11D), C10(H10A,H10B),
 C10A(H10C,H10D)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
  C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru -0.60941(3) -0.72085(2) -0.22918(2) 0.03196(9) Uani 1 1 d . . . . .
Cl1 Cl -0.56929(11) -0.88062(9) -0.15669(7) 0.0503(3) Uani 1 1 d . . . . .
O1 O -0.5014(3) -0.7969(2) -0.31272(15) 0.0408(7) Uani 1 1 d . . . . .
N1 N -0.3982(3) -0.6783(2) -0.20900(16) 0.0323(7) Uani 1 1 d . . . . .
N2 N -0.3119(3) -0.6981(2) -0.27096(18) 0.0362(7) Uani 1 1 d . . . . .
N3 N -0.5051(3) -0.6745(3) -0.05451(17) 0.0375(8) Uani 1 1 d . . . . .
H3 H -0.552893 -0.722534 -0.077618 0.045 Uiso 1 1 calc R . . . .
C1 C -0.3728(4) -0.7615(3) -0.3176(2) 0.0321(8) Uani 1 1 d . . . . .
C2 C -0.2890(4) -0.7970(3) -0.3821(2) 0.0328(8) Uani 1 1 d . . . . .
C3 C -0.1505(4) -0.7644(4) -0.3896(2) 0.0396(9) Uani 1 1 d . . . . .
H3A H -0.109693 -0.720955 -0.353793 0.048 Uiso 1 1 calc R . . . .
C4 C -0.0728(4) -0.7964(4) -0.4503(2) 0.0471(11) Uani 1 1 d . . . . .
H4 H 0.019133 -0.772465 -0.455721 0.057 Uiso 1 1 calc R . . . .
C5 C -0.1304(5) -0.8631(4) -0.5025(2) 0.0493(12) Uani 1 1 d . . . . .
H5 H -0.077077 -0.885515 -0.542531 0.059 Uiso 1 1 calc R . . . .
C6 C -0.2682(5) -0.8967(4) -0.4950(2) 0.0466(11) Uani 1 1 d . . . . .
H6 H -0.307823 -0.941601 -0.530235 0.056 Uiso 1 1 calc R . . . .
C7 C -0.3470(4) -0.8636(3) -0.4354(2) 0.0393(10) Uani 1 1 d . . . . .
H7 H -0.439646 -0.886241 -0.430784 0.047 Uiso 1 1 calc R . . . .
C8 C -0.3380(4) -0.6255(3) -0.1570(2) 0.0340(9) Uani 1 1 d . . . . .
C9 C -0.1984(4) -0.5697(4) -0.1675(2) 0.0439(10) Uani 1 1 d . . . . .
H9AA H -0.184616 -0.553950 -0.219353 0.053 Uiso 0.596(14) 1 calc R . P A 1
H9AB H -0.123180 -0.616904 -0.151655 0.053 Uiso 0.596(14) 1 calc R . P A 1
H9BC H -0.135543 -0.619600 -0.192025 0.053 Uiso 0.404(14) 1 calc R . P A 2
H9BD H -0.212861 -0.509641 -0.200720 0.053 Uiso 0.404(14) 1 calc R . P A 2
C11 C -0.2192(5) -0.4764(4) -0.0431(3) 0.0498(11) Uani 1 1 d . . . . .
H11A H -0.237720 -0.406280 -0.021942 0.060 Uiso 0.596(14) 1 calc R . P A 1
H11B H -0.136496 -0.505989 -0.019400 0.060 Uiso 0.596(14) 1 calc R . P A 1
H11C H -0.167316 -0.466316 0.002314 0.060 Uiso 0.404(14) 1 calc R . P A 2
H11D H -0.250984 -0.406718 -0.060305 0.060 Uiso 0.404(14) 1 calc R . P A 2
C12 C -0.3430(4) -0.5494(3) -0.0302(2) 0.0362(9) Uani 1 1 d . . . . .
C13 C -0.4227(4) -0.5653(3) 0.0349(2) 0.0361(9) Uani 1 1 d . . . . .
C14 C -0.4210(4) -0.5220(4) 0.1067(2) 0.0418(10) Uani 1 1 d . . . . .
H14 H -0.352917 -0.472238 0.120311 0.050 Uiso 1 1 calc R . . . .
C15 C -0.5209(5) -0.5542(4) 0.1559(2) 0.0465(11) Uani 1 1 d . . . . .
H15 H -0.520728 -0.525416 0.203152 0.056 Uiso 1 1 calc R . . . .
C16 C -0.6241(5) -0.6300(4) 0.1367(2) 0.0492(11) Uani 1 1 d . . . . .
H16 H -0.691509 -0.649543 0.171277 0.059 Uiso 1 1 calc R . . . .
C17 C -0.6272(5) -0.6758(4) 0.0679(2) 0.0452(10) Uani 1 1 d . . . . .
H17 H -0.695425 -0.726029 0.055377 0.054 Uiso 1 1 calc R . . . .
C18 C -0.5246(4) -0.6444(3) 0.0176(2) 0.0355(9) Uani 1 1 d . . . . .
C19 C -0.3968(4) -0.6152(3) -0.0835(2) 0.0333(8) Uani 1 1 d . . . . .
C20 C -0.7681(5) -0.6803(4) -0.3093(3) 0.0480(11) Uani 1 1 d . . . . .
H20 H -0.778095 -0.704312 -0.357496 0.058 Uiso 1 1 calc R . . . .
C21 C -0.8336(4) -0.7367(4) -0.2522(3) 0.0486(12) Uani 1 1 d . . . . .
H21 H -0.887614 -0.797164 -0.262326 0.058 Uiso 1 1 calc R . . . .
C22 C -0.8168(4) -0.7008(4) -0.1792(2) 0.0496(12) Uani 1 1 d . . . . .
H22 H -0.857657 -0.738999 -0.140675 0.060 Uiso 1 1 calc R . . . .
C23 C -0.7398(5) -0.6089(4) -0.1644(2) 0.0497(12) Uani 1 1 d . . . . .
H23 H -0.732722 -0.583474 -0.116418 0.060 Uiso 1 1 calc R . . . .
C24 C -0.6719(4) -0.5540(3) -0.2224(3) 0.0483(11) Uani 1 1 d . . . . .
H24 H -0.616257 -0.494449 -0.211993 0.058 Uiso 1 1 calc R . . . .
C25 C -0.6877(5) -0.5883(3) -0.2952(2) 0.0434(11) Uani 1 1 d . . . . .
H25 H -0.645491 -0.550812 -0.333532 0.052 Uiso 1 1 calc R . . . .
C10 C -0.1936(10) -0.4656(8) -0.1233(4) 0.049(3) Uani 0.596(14) 1 d . . P A 1
H10A H -0.102107 -0.432845 -0.130269 0.059 Uiso 0.596(14) 1 calc R . P A 1
H10B H -0.263020 -0.416618 -0.143361 0.059 Uiso 0.596(14) 1 calc R . P A 1
C10A C -0.1260(12) -0.5287(13) -0.1007(7) 0.052(4) Uani 0.404(14) 1 d . . P A 2
H10C H -0.056043 -0.476599 -0.116067 0.062 Uiso 0.404(14) 1 calc R . P A 2
H10D H -0.076614 -0.588048 -0.077762 0.062 Uiso 0.404(14) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 Cl1 2.4144(11) . ?
Ru1 O1 2.063(3) . ?
Ru1 N1 2.112(3) . ?
Ru1 C20 2.157(4) . ?
Ru1 C21 2.184(4) . ?
Ru1 C22 2.188(4) . ?
Ru1 C23 2.205(4) . ?
Ru1 C24 2.163(4) . ?
Ru1 C25 2.170(4) . ?
O1 C1 1.304(4) . ?
N1 N2 1.415(4) . ?
N1 C8 1.285(5) . ?
N2 C1 1.294(5) . ?
N3 C18 1.374(5) . ?
N3 C19 1.374(5) . ?
C1 C2 1.485(5) . ?
C2 C3 1.386(5) . ?
C2 C7 1.388(5) . ?
C3 C4 1.386(6) . ?
C4 C5 1.374(6) . ?
C5 C6 1.384(6) . ?
C6 C7 1.379(6) . ?
C8 C9 1.511(5) . ?
C8 C19 1.453(5) . ?
C9 C10 1.526(9) . ?
C9 C10A 1.486(12) . ?
C11 C12 1.506(6) . ?
C11 C10 1.481(9) . ?
C11 C10A 1.517(12) . ?
C12 C13 1.420(6) . ?
C12 C19 1.368(5) . ?
C13 C14 1.410(5) . ?
C13 C18 1.417(6) . ?
C14 C15 1.365(6) . ?
C15 C16 1.405(7) . ?
C16 C17 1.373(6) . ?
C17 C18 1.394(6) . ?
C20 C21 1.399(6) . ?
C20 C25 1.400(6) . ?
C21 C22 1.408(6) . ?
C22 C23 1.384(7) . ?
C23 C24 1.411(7) . ?
C24 C25 1.397(6) . ?

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 Cl1 86.81(8) . . ?
O1 Ru1 N1 76.55(11) . . ?
O1 Ru1 C20 87.76(15) . . ?
O1 Ru1 C21 107.80(14) . . ?
O1 Ru1 C22 143.88(15) . . ?
O1 Ru1 C23 164.28(15) . . ?
O1 Ru1 C24 128.29(16) . . ?
O1 Ru1 C25 96.54(14) . . ?
N1 Ru1 Cl1 87.76(9) . . ?
N1 Ru1 C20 136.51(15) . . ?
N1 Ru1 C21 170.63(15) . . ?
N1 Ru1 C22 139.38(15) . . ?
N1 Ru1 C23 106.59(15) . . ?
N1 Ru1 C24 90.67(14) . . ?
N1 Ru1 C25 103.44(15) . . ?
C20 Ru1 Cl1 132.15(13) . . ?
C20 Ru1 C21 37.58(17) . . ?
C20 Ru1 C22 67.73(18) . . ?
C20 Ru1 C23 79.48(17) . . ?
C20 Ru1 C24 67.76(17) . . ?
C20 Ru1 C25 37.77(17) . . ?
C21 Ru1 Cl1 100.64(13) . . ?
C21 Ru1 C22 37.57(17) . . ?
C21 Ru1 C23 66.96(17) . . ?
C22 Ru1 Cl1 90.59(13) . . ?
C22 Ru1 C23 36.73(18) . . ?
C23 Ru1 Cl1 108.55(13) . . ?
C24 Ru1 Cl1 143.35(14) . . ?
C24 Ru1 C21 80.13(17) . . ?
C24 Ru1 C22 67.58(18) . . ?
C24 Ru1 C23 37.68(18) . . ?
C24 Ru1 C25 37.63(16) . . ?
C25 Ru1 Cl1 168.76(12) . . ?
C25 Ru1 C21 68.12(17) . . ?
C25 Ru1 C22 80.37(17) . . ?
C25 Ru1 C23 67.75(16) . . ?
C1 O1 Ru1 111.3(2) . . ?
N2 N1 Ru1 111.8(2) . . ?
C8 N1 Ru1 132.9(3) . . ?
C8 N1 N2 114.4(3) . . ?
C1 N2 N1 111.5(3) . . ?
C19 N3 C18 108.7(3) . . ?
O1 C1 C2 117.3(3) . . ?
N2 C1 O1 125.6(3) . . ?
N2 C1 C2 117.2(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 C7 119.0(4) . . ?
C7 C2 C1 120.9(3) . . ?
C4 C3 C2 120.1(4) . . ?
C5 C4 C3 120.6(4) . . ?
C4 C5 C6 119.5(4) . . ?
C7 C6 C5 120.2(4) . . ?
C6 C7 C2 120.5(4) . . ?
N1 C8 C9 122.3(4) . . ?
N1 C8 C19 123.2(3) . . ?
C19 C8 C9 114.5(3) . . ?
C8 C9 C10 110.5(4) . . ?
C10A C9 C8 117.6(5) . . ?
C12 C11 C10A 107.9(5) . . ?
C10 C11 C12 109.7(4) . . ?
C13 C12 C11 129.2(4) . . ?
C19 C12 C11 123.0(4) . . ?
C19 C12 C13 107.8(3) . . ?
C14 C13 C12 135.3(4) . . ?
C14 C13 C18 118.6(4) . . ?
C18 C13 C12 106.1(3) . . ?
C15 C14 C13 119.0(4) . . ?
C14 C15 C16 121.5(4) . . ?
C17 C16 C15 121.2(4) . . ?
C16 C17 C18 117.7(4) . . ?
N3 C18 C13 108.0(3) . . ?
N3 C18 C17 130.0(4) . . ?
C17 C18 C13 121.9(4) . . ?
N3 C19 C8 126.5(3) . . ?
C12 C19 N3 109.4(3) . . ?
C12 C19 C8 123.9(4) . . ?
C21 C20 Ru1 72.3(2) . . ?
C21 C20 C25 121.2(4) . . ?
C25 C20 Ru1 71.6(2) . . ?
C20 C21 Ru1 70.2(2) . . ?
C20 C21 C22 119.3(4) . . ?
C22 C21 Ru1 71.4(2) . . ?
C21 C22 Ru1 71.1(2) . . ?
C23 C22 Ru1 72.3(2) . . ?
C23 C22 C21 120.2(4) . . ?
C22 C23 Ru1 71.0(3) . . ?
C22 C23 C24 119.9(4) . . ?
C24 C23 Ru1 69.6(2) . . ?
C23 C24 Ru1 72.8(3) . . ?
C25 C24 Ru1 71.4(2) . . ?
C25 C24 C23 120.5(4) . . ?
C20 C25 Ru1 70.6(2) . . ?
C24 C25 Ru1 70.9(2) . . ?
C24 C25 C20 118.8(4) . . ?
C11 C10 C9 115.8(6) . . ?
C9 C10A C11 116.0(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_c10mebh
_database_code_depnum_ccdc_archive 'CCDC 1872214'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2018-08-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H19 N3 O2, H2 O'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H19 N3 O2'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
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                   10.8358(6)
_cell_length_b                   7.4023(4)
_cell_length_c                   23.0943(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.837(6)
_cell_angle_gamma                90
_cell_volume                     1839.21(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2437
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.9570
_cell_measurement_theta_min      4.2200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9359
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.493
_diffrn_reflns_theta_min         3.398
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  49.00   1.00    2.93    --    9.75 -99.00 -90.00   31
  2  ω    -13.00  59.00   1.00    2.93    --  -11.93  38.00-180.00   72
  3  ω    -51.00  41.00   1.00    2.93    --  -11.93  19.00 -30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0385870000
_diffrn_orient_matrix_UB_12      -0.0088124000
_diffrn_orient_matrix_UB_13      0.0225842000
_diffrn_orient_matrix_UB_21      -0.0222094000
_diffrn_orient_matrix_UB_22      -0.0839635000
_diffrn_orient_matrix_UB_23      -0.0118334000
_diffrn_orient_matrix_UB_31      0.0486108000
_diffrn_orient_matrix_UB_32      -0.0453463000
_diffrn_orient_matrix_UB_33      0.0175178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2804
_reflns_number_total             4349
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.3380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48674(13) 0.68345(16) -0.06325(6) 0.0639(4) Uani 1 1 d . . . . .
O2 O 0.74516(14) 0.8882(2) -0.28431(6) 0.0804(5) Uani 1 1 d . . . . .
N1 N 0.34717(12) 0.93586(18) -0.02644(6) 0.0450(3) Uani 1 1 d . . . . .
N2 N 0.41071(14) 0.9645(2) -0.07418(6) 0.0476(4) Uani 1 1 d . . . . .
H2 H 0.425(2) 1.071(3) -0.0851(9) 0.082(7) Uiso 1 1 d . . . . .
N3 N 0.21493(14) 0.8712(2) 0.06973(7) 0.0514(4) Uani 1 1 d . . . . .
H3 H 0.2769(19) 0.796(3) 0.0696(9) 0.067(6) Uiso 1 1 d . . . . .
C1 C 0.48145(15) 0.8274(2) -0.09011(7) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.54809(15) 0.8552(2) -0.14178(7) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.52656(19) 0.9979(3) -0.18010(8) 0.0617(5) Uani 1 1 d . . . . .
H3A H 0.4676 1.0845 -0.1735 0.074 Uiso 1 1 calc R . . . .
C4 C 0.5908(2) 1.0150(3) -0.22807(9) 0.0671(6) Uani 1 1 d . . . . .
H4 H 0.5752 1.1123 -0.2534 0.081 Uiso 1 1 calc R . . . .
C5 C 0.67752(17) 0.8876(3) -0.23816(8) 0.0566(5) Uani 1 1 d . . . . .
C6 C 0.70013(19) 0.7449(3) -0.20035(9) 0.0679(6) Uani 1 1 d . . . . .
H6 H 0.7594 0.6587 -0.2069 0.082 Uiso 1 1 calc R . . . .
C7 C 0.63608(19) 0.7288(3) -0.15313(8) 0.0602(5) Uani 1 1 d . . . . .
H7 H 0.6519 0.6309 -0.1281 0.072 Uiso 1 1 calc R . . . .
C8 C 0.27177(14) 1.0595(2) -0.01336(7) 0.0418(4) Uani 1 1 d . . . . .
C9 C 0.24054(16) 1.2342(2) -0.04533(8) 0.0524(4) Uani 1 1 d . . . . .
H9A H 0.1813 1.2097 -0.0793 0.063 Uiso 1 1 calc R . . . .
H9B H 0.3153 1.2821 -0.0589 0.063 Uiso 1 1 calc R . . . .
C10 C 0.18666(18) 1.3754(2) -0.00824(10) 0.0631(5) Uani 1 1 d . . . . .
H10A H 0.1588 1.4772 -0.0328 0.076 Uiso 1 1 calc R . . . .
H10B H 0.2519 1.4182 0.0209 0.076 Uiso 1 1 calc R . . . .
C11 C 0.07899(17) 1.3092(2) 0.02232(9) 0.0578(5) Uani 1 1 d . . . . .
H11A H 0.0599 1.3977 0.0509 0.069 Uiso 1 1 calc R . . . .
H11B H 0.0059 1.2940 -0.0059 0.069 Uiso 1 1 calc R . . . .
C12 C 0.11204(15) 1.1332(2) 0.05180(7) 0.0472(4) Uani 1 1 d . . . . .
C13 C 0.06365(16) 1.0454(3) 0.09897(8) 0.0523(4) Uani 1 1 d . . . . .
C14 C -0.02924(19) 1.0866(3) 0.13418(9) 0.0691(6) Uani 1 1 d . . . . .
H14 H -0.0750 1.1926 0.1282 0.083 Uiso 1 1 calc R . . . .
C15 C -0.0518(2) 0.9697(4) 0.17731(10) 0.0810(7) Uani 1 1 d . . . . .
H15 H -0.1135 0.9969 0.2007 0.097 Uiso 1 1 calc R . . . .
C16 C 0.0154(2) 0.8112(4) 0.18686(10) 0.0809(7) Uani 1 1 d . . . . .
H16 H -0.0025 0.7337 0.2164 0.097 Uiso 1 1 calc R . . . .
C17 C 0.1074(2) 0.7660(3) 0.15386(9) 0.0700(6) Uani 1 1 d . . . . .
H17 H 0.1526 0.6597 0.1608 0.084 Uiso 1 1 calc R . . . .
C18 C 0.13150(16) 0.8836(3) 0.10962(7) 0.0516(4) Uani 1 1 d . . . . .
C19 C 0.20325(15) 1.0243(2) 0.03523(7) 0.0433(4) Uani 1 1 d . . . . .
C20 C 0.7365(3) 1.0376(4) -0.32171(11) 0.0977(9) Uani 1 1 d . . . . .
H20A H 0.7935 1.0231 -0.3502 0.147 Uiso 1 1 calc GR . . . .
H20B H 0.7569 1.1454 -0.2995 0.147 Uiso 1 1 calc GR . . . .
H20C H 0.6533 1.0467 -0.3411 0.147 Uiso 1 1 calc GR . . . .
O3 O 0.44794(13) 0.67656(18) 0.06386(7) 0.0553(3) Uani 1 1 d . . . . .
H3B H 0.439(2) 0.702(3) 0.0293(11) 0.084(8) Uiso 1 1 d . . . . .
H3C H 0.4671(19) 0.560(3) 0.0655(9) 0.071(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2310(19) . ?
O2 C5 1.363(2) . ?
O2 C20 1.400(3) . ?
N1 N2 1.3838(19) . ?
N1 C8 1.287(2) . ?
N2 H2 0.85(2) . ?
N2 C1 1.349(2) . ?
N3 H3 0.87(2) . ?
N3 C18 1.368(2) . ?
N3 C19 1.382(2) . ?
C1 C2 1.481(2) . ?
C2 C3 1.380(2) . ?
C2 C7 1.383(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(3) . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.507(2) . ?
C8 C19 1.441(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.512(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.494(2) . ?
C12 C13 1.421(2) . ?
C12 C19 1.365(2) . ?
C13 C14 1.401(3) . ?
C13 C18 1.412(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O3 H3B 0.81(2) . ?
O3 H3C 0.89(2) . ?

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
C5 O2 C20 118.82(17) . . ?
C8 N1 N2 117.92(13) . . ?
N1 N2 H2 120.5(15) . . ?
C1 N2 N1 117.08(14) . . ?
C1 N2 H2 119.0(15) . . ?
C18 N3 H3 127.9(14) . . ?
C18 N3 C19 108.10(14) . . ?
C19 N3 H3 122.7(14) . . ?
O1 C1 N2 120.50(16) . . ?
O1 C1 C2 121.88(14) . . ?
N2 C1 C2 117.58(14) . . ?
C3 C2 C1 124.15(15) . . ?
C3 C2 C7 117.65(17) . . ?
C7 C2 C1 118.18(15) . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.38(17) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.64(18) . . ?
C5 C4 H4 120.2 . . ?
O2 C5 C4 125.05(18) . . ?
O2 C5 C6 115.29(17) . . ?
C4 C5 C6 119.65(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.34(18) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.33(17) . . ?
C6 C7 H7 119.3 . . ?
N1 C8 C9 127.37(15) . . ?
N1 C8 C19 117.02(14) . . ?
C19 C8 C9 115.49(14) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.25(15) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.28(16) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 C10 109.77(14) . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C13 C12 C11 131.14(16) . . ?
C19 C12 C11 121.99(16) . . ?
C19 C12 C13 106.87(15) . . ?
C14 C13 C12 134.57(19) . . ?
C14 C13 C18 118.59(18) . . ?
C18 C13 C12 106.83(16) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(2) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.0(2) . . ?
C18 C17 H17 121.0 . . ?
N3 C18 C13 108.15(15) . . ?
N3 C18 C17 130.50(18) . . ?
C17 C18 C13 121.34(18) . . ?
N3 C19 C8 125.24(14) . . ?
C12 C19 N3 110.02(15) . . ?
C12 C19 C8 124.65(15) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H3B O3 H3C 105(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
N3 H3 O3 0.87(2) 2.07(2) 2.924(2) 165.1(18) .
O3 H3B N1 0.81(2) 2.31(3) 2.9467(19) 135(2) .
O3 H3C O1 0.89(2) 1.87(2) 2.7578(17) 175(2) 3_665

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.842
####################################################################### 
# 
# 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_c1brbh
_database_code_depnum_ccdc_archive 'CCDC 1872212'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2018-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H16 Br N3 O'
_chemical_formula_sum            'C19 H16 Br N3 O'
_chemical_formula_weight         382.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br1 C19 H16 N3 O1'
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   23.856(4)
_cell_length_b                   8.3192(18)
_cell_length_c                   17.006(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3375.1(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.6120
_cell_measurement_theta_min      3.5320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.416
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  62.00   1.00   14.63    --  -11.93  38.00-150.00   64
  2  ω    -45.00  34.00   1.00   14.63    --  -11.93  77.00 -60.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0222073000
_diffrn_orient_matrix_UB_12      0.0077251000
_diffrn_orient_matrix_UB_13      -0.0275730000
_diffrn_orient_matrix_UB_21      0.0003375000
_diffrn_orient_matrix_UB_22      -0.0843599000
_diffrn_orient_matrix_UB_23      -0.0063723000
_diffrn_orient_matrix_UB_31      -0.0198762000
_diffrn_orient_matrix_UB_32      -0.0100889000
_diffrn_orient_matrix_UB_33      0.0305517000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.575
_reflns_Friedel_fraction_full    0.671
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                4033
_reflns_number_total             6459
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+1.9659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1554
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Others
 Sof(H9AA)=Sof(H9AB)=Sof(H11A)=Sof(H11B)=Sof(C10)=Sof(H10A)=Sof(H10B)=1-FVAR(1)
 Sof(H9BC)=Sof(H9BD)=Sof(H11C)=Sof(H11D)=Sof(C10A)=Sof(H10C)=Sof(H10D)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9BC,H9BD), C9(H9AA,H9AB), C11(H11C,H11D), C11(H11A,H11B), C10(H10A,H10B),
 C10A(H10C,H10D), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), N4(H4A), N6(H6A), C22(H22), C23(H23), C25(H25), C26(H26), C33(H33),
 C34(H34), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32328(4) 0.15185(11) 0.27933(8) 0.0826(4) Uani 1 1 d . . . . .
O1 O 0.1719(3) 0.8524(7) 0.3269(4) 0.0627(16) Uani 1 1 d . . . . .
N1 N 0.2097(3) 0.8991(8) 0.2067(4) 0.0462(16) Uani 1 1 d . . . . .
H1 H 0.226(3) 0.852(9) 0.163(5) 0.04(2) Uiso 1 1 d . . . . .
N2 N 0.1838(2) 1.0468(8) 0.1979(4) 0.0443(16) Uani 1 1 d . . . . .
N3 N 0.1356(3) 1.3577(7) 0.1736(4) 0.0426(15) Uani 1 1 d . . . . .
H3 H 0.1228 1.3173 0.2166 0.051 Uiso 1 1 calc R . . . .
C1 C 0.2012(3) 0.8078(9) 0.2725(5) 0.0431(18) Uani 1 1 d . . . . .
C2 C 0.2319(3) 0.6509(9) 0.2724(5) 0.0401(17) Uani 1 1 d . . . . .
C3 C 0.2096(4) 0.5235(11) 0.3138(5) 0.054(2) Uani 1 1 d . . . . .
H3A H 0.1761 0.5373 0.3408 0.064 Uiso 1 1 calc R . . . .
C4 C 0.2362(4) 0.3753(11) 0.3161(5) 0.061(2) Uani 1 1 d . . . . .
H4 H 0.2204 0.2899 0.3437 0.073 Uiso 1 1 calc R . . . .
C5 C 0.2868(3) 0.3566(10) 0.2765(6) 0.0529(19) Uani 1 1 d . . . . .
C6 C 0.3089(4) 0.4795(12) 0.2341(7) 0.073(3) Uani 1 1 d . . . . .
H6 H 0.3419 0.4647 0.2059 0.088 Uiso 1 1 calc R . . . .
C7 C 0.2819(4) 0.6273(12) 0.2331(6) 0.066(3) Uani 1 1 d . . . . .
H7 H 0.2978 0.7122 0.2054 0.079 Uiso 1 1 calc R . . . .
C8 C 0.1957(3) 1.1244(10) 0.1338(5) 0.0452(19) Uani 1 1 d . . . . .
C9 C 0.2361(4) 1.0725(12) 0.0708(5) 0.061(2) Uani 1 1 d . . . . .
H9BC H 0.2160 1.0079 0.0326 0.073 Uiso 0.52(3) 1 calc R . P A 2
H9BD H 0.2645 1.0047 0.0945 0.073 Uiso 0.52(3) 1 calc R . P A 2
H9AA H 0.2341 0.9567 0.0646 0.073 Uiso 0.48(3) 1 calc R . P A 1
H9AB H 0.2740 1.0998 0.0867 0.073 Uiso 0.48(3) 1 calc R . P A 1
C11 C 0.2208(4) 1.3295(12) -0.0061(6) 0.070(3) Uani 1 1 d . . . . .
H11C H 0.2398 1.4226 -0.0279 0.084 Uiso 0.52(3) 1 calc R . P A 2
H11D H 0.1996 1.2782 -0.0478 0.084 Uiso 0.52(3) 1 calc R . P A 2
H11A H 0.2073 1.3714 -0.0559 0.084 Uiso 0.48(3) 1 calc R . P A 1
H11B H 0.2581 1.3718 0.0031 0.084 Uiso 0.48(3) 1 calc R . P A 1
C12 C 0.1820(3) 1.3806(10) 0.0596(5) 0.049(2) Uani 1 1 d . . . . .
C13 C 0.1516(3) 1.5273(10) 0.0724(5) 0.049(2) Uani 1 1 d . . . . .
C14 C 0.1448(4) 1.6716(11) 0.0310(6) 0.062(3) Uani 1 1 d . . . . .
H14 H 0.1623 1.6875 -0.0172 0.075 Uiso 1 1 calc R . . . .
C15 C 0.1116(5) 1.7885(12) 0.0634(6) 0.071(3) Uani 1 1 d . . . . .
H15 H 0.1065 1.8842 0.0361 0.085 Uiso 1 1 calc R . . . .
C16 C 0.0856(4) 1.7696(12) 0.1344(6) 0.061(3) Uani 1 1 d . . . . .
H16 H 0.0638 1.8530 0.1542 0.073 Uiso 1 1 calc R . . . .
C17 C 0.0909(3) 1.6293(10) 0.1773(6) 0.053(2) Uani 1 1 d . . . . .
H17 H 0.0733 1.6168 0.2258 0.064 Uiso 1 1 calc R . . . .
C18 C 0.1237(3) 1.5070(9) 0.1450(4) 0.0391(17) Uani 1 1 d . . . . .
C19 C 0.1719(3) 1.2818(10) 0.1215(5) 0.0421(19) Uani 1 1 d . . . . .
C10 C 0.2226(15) 1.155(3) -0.0089(14) 0.079(11) Uani 0.48(3) 1 d . . P A 1
H10A H 0.2506 1.1225 -0.0470 0.094 Uiso 0.48(3) 1 calc R . P A 1
H10B H 0.1866 1.1158 -0.0273 0.094 Uiso 0.48(3) 1 calc R . P A 1
C10A C 0.2646(11) 1.209(3) 0.0285(15) 0.075(9) Uani 0.52(3) 1 d . . P A 2
H10C H 0.2876 1.1665 -0.0137 0.090 Uiso 0.52(3) 1 calc R . P A 2
H10D H 0.2891 1.2655 0.0648 0.090 Uiso 0.52(3) 1 calc R . P A 2
Br2 Br 0.42052(5) 0.82466(13) 0.34271(8) 0.0922(4) Uani 1 1 d . . . . .
O2 O 0.5848(2) 0.1424(7) 0.3223(3) 0.0587(16) Uani 1 1 d . . . . .
N4 N 0.5346(3) 0.0889(8) 0.4304(4) 0.0433(16) Uani 1 1 d . . . . .
H4A H 0.5092 0.1213 0.4628 0.052 Uiso 1 1 calc R . . . .
N5 N 0.5612(3) -0.0569(8) 0.4436(4) 0.0423(15) Uani 1 1 d . . . . .
N6 N 0.6124(3) -0.3613(8) 0.4732(4) 0.0439(16) Uani 1 1 d . . . . .
H6A H 0.6280 -0.3198 0.4324 0.053 Uiso 1 1 calc R . . . .
C20 C 0.5477(3) 0.1798(9) 0.3685(4) 0.0396(18) Uani 1 1 d . . . . .
C21 C 0.5153(3) 0.3338(9) 0.3606(4) 0.0407(18) Uani 1 1 d . . . . .
C22 C 0.5422(3) 0.4709(9) 0.3331(5) 0.0450(18) Uani 1 1 d . . . . .
H22 H 0.5795 0.4655 0.3171 0.054 Uiso 1 1 calc R . . . .
C23 C 0.5137(4) 0.6156(10) 0.3293(5) 0.052(2) Uani 1 1 d . . . . .
H23 H 0.5327 0.7081 0.3139 0.063 Uiso 1 1 calc R . . . .
C24 C 0.4575(4) 0.6246(10) 0.3481(6) 0.059(2) Uani 1 1 d . . . . .
C25 C 0.4300(4) 0.4893(13) 0.3718(6) 0.065(3) Uani 1 1 d . . . . .
H25 H 0.3920 0.4945 0.3839 0.078 Uiso 1 1 calc R . . . .
C26 C 0.4586(4) 0.3416(11) 0.3781(6) 0.057(2) Uani 1 1 d . . . . .
H26 H 0.4395 0.2497 0.3939 0.068 Uiso 1 1 calc R . . . .
C27 C 0.5482(3) -0.1320(10) 0.5068(5) 0.0416(19) Uani 1 1 d . . . . .
C28 C 0.5063(3) -0.0801(10) 0.5700(5) 0.054(2) Uani 1 1 d . . . . .
H28A H 0.5079 0.0358 0.5760 0.065 Uiso 1 1 calc R . . . .
H28B H 0.4687 -0.1080 0.5531 0.065 Uiso 1 1 calc R . . . .
C29 C 0.5178(4) -0.1584(10) 0.6490(5) 0.054(2) Uani 1 1 d . . . . .
H29A H 0.4889 -0.1266 0.6859 0.065 Uiso 1 1 calc R . . . .
H29B H 0.5534 -0.1201 0.6690 0.065 Uiso 1 1 calc R . . . .
C30 C 0.5193(4) -0.3417(10) 0.6437(6) 0.056(2) Uani 1 1 d . . . . .
H30A H 0.5313 -0.3865 0.6936 0.067 Uiso 1 1 calc R . . . .
H30B H 0.4822 -0.3826 0.6321 0.067 Uiso 1 1 calc R . . . .
C31 C 0.5586(3) -0.3902(10) 0.5813(4) 0.0427(18) Uani 1 1 d . . . . .
C32 C 0.5891(3) -0.5365(10) 0.5700(4) 0.0431(18) Uani 1 1 d . . . . .
C33 C 0.5927(4) -0.6856(10) 0.6082(5) 0.052(2) Uani 1 1 d . . . . .
H33 H 0.5714 -0.7041 0.6531 0.062 Uiso 1 1 calc R . . . .
C34 C 0.6273(4) -0.8041(11) 0.5804(6) 0.058(2) Uani 1 1 d . . . . .
H34 H 0.6300 -0.9015 0.6069 0.070 Uiso 1 1 calc R . . . .
C35 C 0.6584(4) -0.7779(11) 0.5117(6) 0.058(2) Uani 1 1 d . . . . .
H35 H 0.6810 -0.8606 0.4929 0.070 Uiso 1 1 calc R . . . .
C36 C 0.6570(4) -0.6352(11) 0.4710(5) 0.052(2) Uani 1 1 d . . . . .
H36 H 0.6779 -0.6197 0.4255 0.063 Uiso 1 1 calc R . . . .
C37 C 0.6221(3) -0.5134(9) 0.5018(4) 0.0409(18) Uani 1 1 d . . . . .
C38 C 0.5734(3) -0.2864(10) 0.5203(5) 0.0408(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.914(8) . ?
O1 C1 1.216(9) . ?
N1 H1 0.94(8) . ?
N1 N2 1.384(9) . ?
N1 C1 1.368(11) . ?
N2 C8 1.299(10) . ?
N3 H3 0.8600 . ?
N3 C18 1.364(9) . ?
N3 C19 1.390(10) . ?
C1 C2 1.497(10) . ?
C2 C3 1.379(11) . ?
C2 C7 1.382(11) . ?
C3 H3A 0.9300 . ?
C3 C4 1.386(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(12) . ?
C5 C6 1.358(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(11) . ?
C8 C19 1.442(11) . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 C10 1.55(3) . ?
C9 C10A 1.51(2) . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(13) . ?
C11 C10 1.45(3) . ?
C11 C10A 1.56(3) . ?
C12 C13 1.437(11) . ?
C12 C19 1.358(11) . ?
C13 C14 1.402(12) . ?
C13 C18 1.412(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.397(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
Br2 C24 1.885(9) . ?
O2 C20 1.223(9) . ?
N4 H4A 0.8600 . ?
N4 N5 1.387(8) . ?
N4 C20 1.334(9) . ?
N5 C27 1.282(9) . ?
N6 H6A 0.8600 . ?
N6 C37 1.376(9) . ?
N6 C38 1.376(10) . ?
C20 C21 1.501(10) . ?
C21 C22 1.390(10) . ?
C21 C26 1.388(11) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(12) . ?
C24 C25 1.364(13) . ?
C25 H25 0.9300 . ?
C25 C26 1.409(12) . ?
C26 H26 0.9300 . ?
C27 C28 1.531(11) . ?
C27 C38 1.437(11) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.517(12) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.528(11) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.472(11) . ?
C31 C32 1.431(11) . ?
C31 C38 1.395(12) . ?
C32 C33 1.403(11) . ?
C32 C37 1.415(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.369(12) . ?
C34 H34 0.9300 . ?
C34 C35 1.401(14) . ?
C35 H35 0.9300 . ?
C35 C36 1.375(13) . ?
C36 H36 0.9300 . ?
C36 C37 1.412(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 119(5) . . ?
C1 N1 H1 119(5) . . ?
C1 N1 N2 121.0(7) . . ?
C8 N2 N1 115.7(6) . . ?
C18 N3 H3 125.8 . . ?
C18 N3 C19 108.4(6) . . ?
C19 N3 H3 125.8 . . ?
O1 C1 N1 122.5(8) . . ?
O1 C1 C2 123.3(8) . . ?
N1 C1 C2 114.2(7) . . ?
C3 C2 C1 118.8(7) . . ?
C3 C2 C7 118.1(8) . . ?
C7 C2 C1 123.2(7) . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.5(8) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.8(8) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Br1 118.9(7) . . ?
C6 C5 Br1 120.4(7) . . ?
C6 C5 C4 120.7(8) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.5(8) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 121.4(8) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 C9 126.5(7) . . ?
N2 C8 C19 119.1(7) . . ?
C19 C8 C9 114.2(7) . . ?
C8 C9 H9BC 108.7 . . ?
C8 C9 H9BD 108.7 . . ?
C8 C9 H9AA 109.4 . . ?
C8 C9 H9AB 109.4 . . ?
C8 C9 C10 111.2(11) . . ?
C8 C9 C10A 114.4(10) . . ?
H9BC C9 H9BD 107.6 . . ?
H9AA C9 H9AB 108.0 . . ?
C10 C9 H9AA 109.4 . . ?
C10 C9 H9AB 109.4 . . ?
C10A C9 H9BC 108.7 . . ?
C10A C9 H9BD 108.7 . . ?
H11C C11 H11D 108.4 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11C 110.1 . . ?
C12 C11 H11D 110.1 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C12 C11 C10A 108.1(10) . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C10 C11 C12 108.8(11) . . ?
C10A C11 H11C 110.1 . . ?
C10A C11 H11D 110.1 . . ?
C13 C12 C11 131.4(8) . . ?
C19 C12 C11 120.8(8) . . ?
C19 C12 C13 107.8(7) . . ?
C14 C13 C12 135.1(8) . . ?
C14 C13 C18 119.2(8) . . ?
C18 C13 C12 105.6(7) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.1(9) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.5(9) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(10) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 121.4 . . ?
C16 C17 C18 117.3(9) . . ?
C18 C17 H17 121.4 . . ?
N3 C18 C13 108.8(7) . . ?
N3 C18 C17 129.8(7) . . ?
C17 C18 C13 121.4(8) . . ?
N3 C19 C8 124.4(7) . . ?
C12 C19 N3 109.3(7) . . ?
C12 C19 C8 126.3(7) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 C9 115(2) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C9 C10A C11 111.2(17) . . ?
C9 C10A H10C 109.4 . . ?
C9 C10A H10D 109.4 . . ?
C11 C10A H10C 109.4 . . ?
C11 C10A H10D 109.4 . . ?
H10C C10A H10D 108.0 . . ?
N5 N4 H4A 119.5 . . ?
C20 N4 H4A 119.5 . . ?
C20 N4 N5 121.0(6) . . ?
C27 N5 N4 116.7(6) . . ?
C37 N6 H6A 125.5 . . ?
C38 N6 H6A 125.5 . . ?
C38 N6 C37 109.0(7) . . ?
O2 C20 N4 122.1(7) . . ?
O2 C20 C21 122.1(7) . . ?
N4 C20 C21 115.7(7) . . ?
C22 C21 C20 119.6(7) . . ?
C26 C21 C20 121.5(7) . . ?
C26 C21 C22 118.9(7) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(7) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(8) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 Br2 119.4(7) . . ?
C25 C24 Br2 121.2(7) . . ?
C25 C24 C23 119.4(8) . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(8) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 119.8(8) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N5 C27 C28 127.6(7) . . ?
N5 C27 C38 117.9(7) . . ?
C38 C27 C28 114.5(7) . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 C27 112.5(6) . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C28 C29 C30 112.4(7) . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C29 C30 H30A 109.8 . . ?
C29 C30 H30B 109.8 . . ?
H30A C30 H30B 108.3 . . ?
C31 C30 C29 109.3(7) . . ?
C31 C30 H30A 109.8 . . ?
C31 C30 H30B 109.8 . . ?
C32 C31 C30 130.8(7) . . ?
C38 C31 C30 121.9(7) . . ?
C38 C31 C32 107.3(7) . . ?
C33 C32 C31 136.2(8) . . ?
C33 C32 C37 117.7(7) . . ?
C37 C32 C31 106.1(7) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.9(8) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(9) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 118.6 . . ?
C36 C35 C34 122.7(9) . . ?
C36 C35 H35 118.6 . . ?
C35 C36 H36 121.7 . . ?
C35 C36 C37 116.6(8) . . ?
C37 C36 H36 121.7 . . ?
N6 C37 C32 108.7(7) . . ?
N6 C37 C36 128.9(8) . . ?
C36 C37 C32 122.4(7) . . ?
N6 C38 C27 126.5(8) . . ?
N6 C38 C31 108.9(7) . . ?
C31 C38 C27 124.5(7) . . ?

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
N3 H3 O2 0.86 2.04 2.805(8) 147.3 4_465
C3 H3A O2 0.93 2.66 3.285(10) 125.3 4_455
C17 H17 O2 0.93 2.72 3.348(11) 125.2 4_465
N6 H6A O1 0.86 2.10 2.866(8) 148.8 4

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.892
_oxdiff_exptl_absorpt_empirical_full_min 0.745
####################################################################### 
# 
# 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_bc1omebh
_database_code_depnum_ccdc_archive 'CCDC 1916479'
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Cl N3 O2 Ru'
_chemical_formula_sum            'C26 H24 Cl N3 O2 Ru'
_chemical_formula_weight         547.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 Cl1 H25 N3 O2 Ru1'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.4635(3)
_cell_length_b                   12.8709(4)
_cell_length_c                   16.2088(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.314(3)
_cell_angle_gamma                90
_cell_volume                     2270.40(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.3930
_cell_measurement_theta_min      3.7340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21470
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.479
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  62.00   1.00    4.22    --  -11.78  70.00 -71.00  105
  2  ω    -85.00  19.00   1.00    4.22    --  -11.78 -70.00 156.00  104
  3  ω    -85.00  16.00   1.00    4.22    --  -11.78 -57.00   0.00  101
  4  ω    -94.00 -54.00   1.00    4.22    --  -11.78-179.00 -60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0023568000
_diffrn_orient_matrix_UB_12      0.0423523000
_diffrn_orient_matrix_UB_13      0.0274172000
_diffrn_orient_matrix_UB_21      -0.0267445000
_diffrn_orient_matrix_UB_22      -0.0327334000
_diffrn_orient_matrix_UB_23      0.0243303000
_diffrn_orient_matrix_UB_31      0.0594033000
_diffrn_orient_matrix_UB_32      -0.0130715000
_diffrn_orient_matrix_UB_33      0.0279521000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4457
_reflns_number_total             5480
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+1.4944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.14302(2) 0.13070(2) 0.19179(2) 0.03295(7) Uani 1 1 d . . . . .
Cl1 Cl 0.21026(6) -0.02507(5) 0.13653(4) 0.04471(16) Uani 1 1 d . . . . .
O1 O 0.15083(15) 0.04521(15) 0.30073(10) 0.0403(4) Uani 1 1 d . . . . .
O2 O 0.2566(2) -0.07559(16) 0.69616(12) 0.0563(5) Uani 1 1 d . . . . .
N1 N 0.32224(18) 0.15507(16) 0.27425(12) 0.0317(4) Uani 1 1 d . . . . .
N2 N 0.33673(19) 0.12791(16) 0.36067(12) 0.0343(4) Uani 1 1 d . . . . .
N3 N 0.38061(19) 0.15971(18) 0.10781(13) 0.0398(5) Uani 1 1 d . . . . .
H3 H 0.316465 0.121288 0.098958 0.048 Uiso 1 1 calc R . . . .
C1 C 0.2469(2) 0.06880(19) 0.36547(14) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.2544(2) 0.02645(19) 0.45238(14) 0.0325(5) Uani 1 1 d . . . . .
C3 C 0.3566(2) 0.0451(2) 0.52398(15) 0.0390(6) Uani 1 1 d . . . . .
H3A H 0.423471 0.080492 0.516807 0.047 Uiso 1 1 calc R . . . .
C4 C 0.3606(2) 0.0117(2) 0.60579(16) 0.0429(6) Uani 1 1 d . . . . .
H4 H 0.429675 0.024903 0.653245 0.052 Uiso 1 1 calc R . . . .
C5 C 0.2619(2) -0.04110(19) 0.61709(15) 0.0388(6) Uani 1 1 d . . . . .
C6 C 0.1612(3) -0.0639(2) 0.54560(16) 0.0437(6) Uani 1 1 d . . . . .
H6 H 0.096201 -0.102338 0.552443 0.052 Uiso 1 1 calc R . . . .
C7 C 0.1576(2) -0.0293(2) 0.46429(16) 0.0425(6) Uani 1 1 d . . . . .
H7 H 0.089084 -0.043711 0.416724 0.051 Uiso 1 1 calc R . . . .
C8 C 0.3420(3) -0.0348(3) 0.77165(19) 0.0635(9) Uani 1 1 d . . . . .
H8A H 0.335502 0.039585 0.771094 0.095 Uiso 1 1 calc GR . . . .
H8B H 0.423561 -0.054324 0.773405 0.095 Uiso 1 1 calc GR . . . .
H8C H 0.325216 -0.061791 0.821971 0.095 Uiso 1 1 calc GR . . . .
C9 C 0.4130(2) 0.20863(18) 0.26382(14) 0.0312(5) Uani 1 1 d . . . . .
C10 C 0.5096(2) 0.2573(2) 0.33958(15) 0.0383(6) Uani 1 1 d . . . . .
H10A H 0.575895 0.208133 0.362875 0.046 Uiso 1 1 calc R . . . .
H10B H 0.473990 0.273371 0.385033 0.046 Uiso 1 1 calc R . . . .
C11 C 0.5610(3) 0.3564(2) 0.31280(18) 0.0455(6) Uani 1 1 d . . . . .
H11A H 0.495860 0.407604 0.294703 0.055 Uiso 1 1 calc R . . . .
H11B H 0.624252 0.384148 0.362829 0.055 Uiso 1 1 calc R . . . .
C12 C 0.6150(3) 0.3398(2) 0.23968(19) 0.0488(7) Uani 1 1 d . . . . .
H12A H 0.626011 0.406365 0.215029 0.059 Uiso 1 1 calc R . . . .
H12B H 0.694917 0.306944 0.262262 0.059 Uiso 1 1 calc R . . . .
C13 C 0.5322(2) 0.27310(19) 0.17087(16) 0.0366(5) Uani 1 1 d . . . . .
C14 C 0.5431(2) 0.2440(2) 0.08871(16) 0.0376(5) Uani 1 1 d . . . . .
C15 C 0.6278(3) 0.2670(2) 0.04514(18) 0.0480(7) Uani 1 1 d . . . . .
H15 H 0.690330 0.315060 0.067839 0.058 Uiso 1 1 calc R . . . .
C16 C 0.6166(3) 0.2173(3) -0.0315(2) 0.0581(8) Uani 1 1 d . . . . .
H16 H 0.673281 0.231041 -0.060419 0.070 Uiso 1 1 calc R . . . .
C17 C 0.5230(3) 0.1472(3) -0.0669(2) 0.0608(9) Uani 1 1 d . . . . .
H17 H 0.518491 0.114875 -0.119142 0.073 Uiso 1 1 calc R . . . .
C18 C 0.4359(3) 0.1237(2) -0.02730(18) 0.0510(7) Uani 1 1 d . . . . .
H18 H 0.372206 0.077310 -0.051990 0.061 Uiso 1 1 calc R . . . .
C19 C 0.4481(2) 0.1728(2) 0.05154(15) 0.0382(5) Uani 1 1 d . . . . .
C20 C 0.4343(2) 0.21936(19) 0.18114(14) 0.0337(5) Uani 1 1 d . . . . .
C21 C 0.0950(4) 0.2295(4) 0.0772(2) 0.0769(12) Uani 1 1 d . . . . .
H21 H 0.132163 0.237142 0.034193 0.092 Uiso 1 1 calc R . . . .
C22 C 0.0026(4) 0.1570(3) 0.0671(2) 0.0826(14) Uani 1 1 d . . . . .
H22 H -0.021524 0.114801 0.018038 0.099 Uiso 1 1 calc R . . . .
C23 C -0.0548(3) 0.1479(3) 0.1325(4) 0.0875(15) Uani 1 1 d . . . . .
H23 H -0.118359 0.100937 0.127219 0.105 Uiso 1 1 calc R . . . .
C24 C -0.0111(4) 0.2136(4) 0.2067(3) 0.0795(12) Uani 1 1 d . . . . .
H24 H -0.045184 0.208501 0.251529 0.095 Uiso 1 1 calc R . . . .
C25 C 0.0789(4) 0.2830(3) 0.2125(2) 0.0747(11) Uani 1 1 d . . . . .
H25 H 0.104916 0.326808 0.260398 0.090 Uiso 1 1 calc R . . . .
C26 C 0.1315(3) 0.2892(3) 0.1491(3) 0.0741(11) Uani 1 1 d . . . . .
H26 H 0.195195 0.336215 0.155190 0.089 Uiso 1 1 calc R . . . .


_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 Cl1 2.4187(7) . ?
Ru1 O1 2.0586(17) . ?
Ru1 N1 2.0928(19) . ?
Ru1 C21 2.174(3) . ?
Ru1 C22 2.179(3) . ?
Ru1 C23 2.178(3) . ?
Ru1 C24 2.141(3) . ?
Ru1 C25 2.156(3) . ?
Ru1 C26 2.144(3) . ?
O1 C1 1.296(3) . ?
O2 C5 1.376(3) . ?
O2 C8 1.407(4) . ?
N1 N2 1.402(3) . ?
N1 C9 1.303(3) . ?
N2 C1 1.303(3) . ?
N3 C19 1.379(3) . ?
N3 C20 1.386(3) . ?
C1 C2 1.487(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.386(4) . ?
C6 C7 1.379(3) . ?
C9 C10 1.507(3) . ?
C9 C20 1.442(3) . ?
C10 C11 1.524(4) . ?
C11 C12 1.515(4) . ?
C12 C13 1.489(4) . ?
C13 C14 1.426(3) . ?
C13 C20 1.372(3) . ?
C14 C15 1.401(4) . ?
C14 C19 1.405(4) . ?
C15 C16 1.366(4) . ?
C16 C17 1.382(5) . ?
C17 C18 1.380(4) . ?
C18 C19 1.393(4) . ?
C21 C22 1.381(6) . ?
C21 C26 1.348(6) . ?
C22 C23 1.417(6) . ?
C23 C24 1.427(6) . ?
C24 C25 1.345(6) . ?
C25 C26 1.346(6) . ?

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 Cl1 86.65(5) . . ?
O1 Ru1 N1 76.28(7) . . ?
O1 Ru1 C21 167.55(11) . . ?
O1 Ru1 C22 134.37(16) . . ?
O1 Ru1 C23 101.05(14) . . ?
O1 Ru1 C24 89.14(12) . . ?
O1 Ru1 C25 106.12(13) . . ?
O1 Ru1 C26 140.06(14) . . ?
N1 Ru1 Cl1 89.86(6) . . ?
N1 Ru1 C21 113.10(14) . . ?
N1 Ru1 C22 149.32(17) . . ?
N1 Ru1 C23 160.66(16) . . ?
N1 Ru1 C24 122.16(14) . . ?
N1 Ru1 C25 94.51(12) . . ?
N1 Ru1 C26 90.69(11) . . ?
C21 Ru1 Cl1 101.14(12) . . ?
C21 Ru1 C22 37.01(16) . . ?
C21 Ru1 C23 67.31(16) . . ?
C22 Ru1 Cl1 90.78(10) . . ?
C23 Ru1 Cl1 109.23(14) . . ?
C23 Ru1 C22 37.97(17) . . ?
C24 Ru1 Cl1 145.60(15) . . ?
C24 Ru1 C21 78.94(14) . . ?
C24 Ru1 C22 68.41(16) . . ?
C24 Ru1 C23 38.56(17) . . ?
C24 Ru1 C25 36.47(16) . . ?
C24 Ru1 C26 65.96(17) . . ?
C25 Ru1 Cl1 167.15(12) . . ?
C25 Ru1 C21 66.04(16) . . ?
C25 Ru1 C22 79.32(14) . . ?
C25 Ru1 C23 67.54(16) . . ?
C26 Ru1 Cl1 131.57(14) . . ?
C26 Ru1 C21 36.37(16) . . ?
C26 Ru1 C22 66.44(16) . . ?
C26 Ru1 C23 79.10(14) . . ?
C26 Ru1 C25 36.49(16) . . ?
C1 O1 Ru1 111.49(15) . . ?
C5 O2 C8 117.9(2) . . ?
N2 N1 Ru1 112.65(14) . . ?
C9 N1 Ru1 131.32(15) . . ?
C9 N1 N2 114.39(18) . . ?
C1 N2 N1 110.96(18) . . ?
C19 N3 C20 108.0(2) . . ?
O1 C1 N2 125.1(2) . . ?
O1 C1 C2 117.6(2) . . ?
N2 C1 C2 117.3(2) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 120.7(2) . . ?
C7 C2 C3 118.4(2) . . ?
C4 C3 C2 121.0(2) . . ?
C5 C4 C3 120.0(2) . . ?
O2 C5 C4 124.1(2) . . ?
O2 C5 C6 116.2(2) . . ?
C4 C5 C6 119.7(2) . . ?
C7 C6 C5 119.9(2) . . ?
C6 C7 C2 121.0(2) . . ?
N1 C9 C10 121.8(2) . . ?
N1 C9 C20 123.1(2) . . ?
C20 C9 C10 114.9(2) . . ?
C9 C10 C11 111.5(2) . . ?
C12 C11 C10 113.2(2) . . ?
C13 C12 C11 110.2(2) . . ?
C14 C13 C12 128.9(2) . . ?
C20 C13 C12 123.6(2) . . ?
C20 C13 C14 107.2(2) . . ?
C15 C14 C13 133.9(3) . . ?
C15 C14 C19 119.2(2) . . ?
C19 C14 C13 106.8(2) . . ?
C16 C15 C14 118.5(3) . . ?
C15 C16 C17 121.5(3) . . ?
C18 C17 C16 122.1(3) . . ?
C17 C18 C19 116.6(3) . . ?
N3 C19 C14 108.4(2) . . ?
N3 C19 C18 129.4(3) . . ?
C18 C19 C14 122.0(2) . . ?
N3 C20 C9 125.8(2) . . ?
C13 C20 N3 109.6(2) . . ?
C13 C20 C9 123.0(2) . . ?
C22 C21 Ru1 71.7(2) . . ?
C26 C21 Ru1 70.62(19) . . ?
C26 C21 C22 120.4(4) . . ?
C21 C22 Ru1 71.30(18) . . ?
C21 C22 C23 119.0(3) . . ?
C23 C22 Ru1 70.99(19) . . ?
C22 C23 Ru1 71.04(19) . . ?
C22 C23 C24 117.3(4) . . ?
C24 C23 Ru1 69.33(19) . . ?
C23 C24 Ru1 72.1(2) . . ?
C25 C24 Ru1 72.4(2) . . ?
C25 C24 C23 120.7(4) . . ?
C24 C25 Ru1 71.2(2) . . ?
C24 C25 C26 120.2(4) . . ?
C26 C25 Ru1 71.3(2) . . ?
C21 C26 Ru1 73.0(2) . . ?
C25 C26 Ru1 72.2(2) . . ?
C25 C26 C21 122.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.804
