# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_mo_2017911-85-8_0m
_database_code_depnum_ccdc_archive 'CCDC 1586057'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 Cl N2 O'
_chemical_formula_sum            'C18 H17 Cl N2 O'
_chemical_formula_weight         312.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.075(4)
_cell_length_b                   8.096(4)
_cell_length_c                   13.744(6)
_cell_angle_alpha                94.419(12)
_cell_angle_beta                 104.016(11)
_cell_angle_gamma                113.589(11)
_cell_volume                     783.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    273
_cell_measurement_temperature    173
_cell_measurement_theta_max      17.363
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0869 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.7957. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.1645
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6052
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         1.557
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1293
_reflns_number_total             2837
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1652
_refine_ls_R_factor_gt           0.0813
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2399
_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. Restrained distances
 C19-C13 = C18-C15
 1.54 with sigma of 0.02
 C18-C15 \\sim C19-C13
 with sigma of 0.02
3. Rigid bond restraints
 C19, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C13 \\sim C19: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C18 \\sim C15: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C18) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: Cl1(0.6) C18(0.4) H18A(0.4) H18B(0.4) H18C(0.4) Cl2(0.4) C19(0.6)
 H19A(0.6) H19B(0.6) H19C(0.6)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C4(H4), C2(H2), C1(H1), C3(H3)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C10(H10A,H10B,
 H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.2669(10) 1.2987(6) 0.4546(5) 0.0643(13) Uani 0.6 1 d . . P A 1
C18 C 0.251(5) 1.268(3) 0.466(2) 0.039(6) Uani 0.4 1 d D U P A 2
H18A H 0.1228 1.2486 0.4660 0.058 Uiso 0.4 1 calc GR . P A 2
H18B H 0.2869 1.3406 0.4144 0.058 Uiso 0.4 1 calc GR . P A 2
H18C H 0.3402 1.3340 0.5336 0.058 Uiso 0.4 1 calc GR . P A 2
Cl2 Cl 0.240(2) 0.6834(16) 0.5953(6) 0.061(2) Uani 0.4 1 d . . P B 2
C19 C 0.269(5) 0.708(4) 0.5958(19) 0.081(10) Uani 0.6 1 d D U P B 1
H19A H 0.2846 0.5991 0.5726 0.122 Uiso 0.6 1 calc GR . P B 1
H19B H 0.1570 0.6713 0.6195 0.122 Uiso 0.6 1 calc GR . P B 1
H19C H 0.3817 0.7905 0.6521 0.122 Uiso 0.6 1 calc GR . P B 1
O1 O 0.6210(5) 0.8238(5) 0.0695(3) 0.0648(12) Uani 1 1 d . . . . .
N2 N 0.4491(6) 0.5906(6) 0.1351(3) 0.0420(11) Uani 1 1 d . . . . .
N1 N 0.3122(6) 0.8711(6) 0.1727(3) 0.0431(11) Uani 1 1 d . . . . .
C11 C 0.2417(6) 0.8281(6) 0.3290(4) 0.0344(12) Uani 1 1 d . . . . .
C5 C 0.1755(6) 0.5533(6) 0.1954(3) 0.0338(11) Uani 1 1 d . . . . .
C12 C 0.2427(6) 0.7359(6) 0.4086(4) 0.0364(12) Uani 1 1 d . . . . .
H12 H 0.2412 0.6178 0.3982 0.044 Uiso 1 1 calc R . . . .
C16 C 0.2471(7) 1.0009(6) 0.3462(4) 0.0384(12) Uani 1 1 d . . . . .
H16 H 0.2460 1.0672 0.2921 0.046 Uiso 1 1 calc R . . . .
C7 C 0.2471(6) 0.7543(6) 0.2281(4) 0.0368(12) Uani 1 1 d . . . . .
C15 C 0.2538(7) 1.0779(6) 0.4402(4) 0.0407(13) Uani 1 1 d D U . . .
C4 C 0.0066(7) 0.4329(7) 0.2092(4) 0.0380(12) Uani 1 1 d . . . . .
H4 H -0.0604 0.4820 0.2410 0.046 Uiso 1 1 calc R . . . .
C6 C 0.2719(7) 0.4771(7) 0.1486(3) 0.0362(12) Uani 1 1 d . . . . .
C13 C 0.2458(6) 0.8110(7) 0.5051(4) 0.0407(13) Uani 1 1 d D U . . .
C14 C 0.2539(6) 0.9872(7) 0.5227(4) 0.0391(12) Uani 1 1 d . . . . .
C9 C 0.4735(7) 0.7393(7) 0.0894(4) 0.0419(13) Uani 1 1 d . . . . .
C2 C 0.0301(7) 0.1728(7) 0.1326(4) 0.0455(14) Uani 1 1 d . . . . .
H2 H -0.0193 0.0436 0.1107 0.055 Uiso 1 1 calc R . . . .
C1 C 0.2003(7) 0.2892(7) 0.1187(4) 0.0454(13) Uani 1 1 d . . . . .
H1 H 0.2680 0.2388 0.0884 0.055 Uiso 1 1 calc R . . . .
C3 C -0.0669(7) 0.2460(7) 0.1785(4) 0.0453(14) Uani 1 1 d . . . . .
H3 H -0.1831 0.1677 0.1887 0.054 Uiso 1 1 calc R . . . .
C8 C 0.3155(8) 0.7968(7) 0.0745(4) 0.0478(14) Uani 1 1 d . . . . .
H8A H 0.3340 0.8908 0.0311 0.057 Uiso 1 1 calc R . . . .
H8B H 0.1931 0.6896 0.0396 0.057 Uiso 1 1 calc R . . . .
C17 C 0.2591(8) 1.0724(8) 0.6238(4) 0.0565(15) Uani 1 1 d . . . . .
H17A H 0.3400 1.2049 0.6375 0.085 Uiso 1 1 calc GR . . . .
H17B H 0.3102 1.0173 0.6772 0.085 Uiso 1 1 calc GR . . . .
H17C H 0.1306 1.0514 0.6232 0.085 Uiso 1 1 calc GR . . . .
C10 C 0.6037(7) 0.5344(8) 0.1589(5) 0.0599(17) Uani 1 1 d . . . . .
H10A H 0.5999 0.4749 0.2183 0.090 Uiso 1 1 calc GR . . . .
H10B H 0.7253 0.6428 0.1742 0.090 Uiso 1 1 calc GR . . . .
H10C H 0.5891 0.4479 0.1000 0.090 Uiso 1 1 calc GR . . . .


_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
Cl1 C15 1.741(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C15 1.565(15) . ?
Cl2 C13 1.671(9) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C13 1.566(14) . ?
O1 C9 1.223(6) . ?
N2 C6 1.424(6) . ?
N2 C9 1.368(6) . ?
N2 C10 1.467(6) . ?
N1 C7 1.287(5) . ?
N1 C8 1.445(6) . ?
C11 C12 1.371(6) . ?
C11 C16 1.383(6) . ?
C11 C7 1.485(7) . ?
C5 C7 1.481(7) . ?
C5 C4 1.391(6) . ?
C5 C6 1.402(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.407(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.370(7) . ?
C15 C14 1.397(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.371(6) . ?
C6 C1 1.379(7) . ?
C13 C14 1.401(6) . ?
C14 C17 1.487(7) . ?
C9 C8 1.500(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.390(7) . ?
C2 C3 1.385(7) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
C6 N2 C10 119.3(4) . . ?
C9 N2 C6 122.0(4) . . ?
C9 N2 C10 118.3(4) . . ?
C7 N1 C8 116.4(4) . . ?
C12 C11 C16 118.1(5) . . ?
C12 C11 C7 122.5(4) . . ?
C16 C11 C7 119.3(4) . . ?
C4 C5 C7 120.5(4) . . ?
C4 C5 C6 117.6(5) . . ?
C6 C5 C7 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 121.9(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
N1 C7 C11 117.2(4) . . ?
N1 C7 C5 123.5(5) . . ?
C5 C7 C11 119.3(4) . . ?
C16 C15 Cl1 117.1(4) . . ?
C16 C15 C18 124.7(12) . . ?
C16 C15 C14 122.5(4) . . ?
C14 C15 Cl1 120.5(5) . . ?
C14 C15 C18 112.8(12) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 C5 122.5(5) . . ?
C3 C4 H4 118.7 . . ?
C5 C6 N2 121.0(4) . . ?
C1 C6 N2 118.7(4) . . ?
C1 C6 C5 120.3(4) . . ?
C12 C13 Cl2 117.7(5) . . ?
C12 C13 C19 119.2(13) . . ?
C14 C13 Cl2 122.5(5) . . ?
C14 C13 C19 120.5(13) . . ?
C14 C13 C12 119.8(5) . . ?
C15 C14 C13 116.9(5) . . ?
C15 C14 C17 121.6(5) . . ?
C13 C14 C17 121.6(5) . . ?
O1 C9 N2 120.8(5) . . ?
O1 C9 C8 123.9(5) . . ?
N2 C9 C8 115.2(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.6(5) . . ?
C6 C1 C2 120.7(5) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N1 C8 C9 109.6(4) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
####################################################################### 
# 
# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 1587232'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Cl N4'
_chemical_formula_sum            'C15 H15 Cl N4'
_chemical_formula_weight         286.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 1 21/c 1'
_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                   13.886(12)
_cell_length_b                   14.758(12)
_cell_length_c                   6.953(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.04(2)
_cell_angle_gamma                90
_cell_volume                     1393(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    350
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.505
_cell_measurement_theta_min      2.760
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1012 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.7465. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6999
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.499
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1119
_reflns_number_total             2376
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0929
_refine_ls_restrained_S_all      0.925
_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)+(0.1200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C6(H6), C7(H7), C12(H12)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.05673(10) 0.88035(10) 0.0227(2) 0.0435(6) Uani 1 1 d . . . . .
N2 N 0.6072(3) 0.7927(3) 0.3314(7) 0.0327(12) Uani 1 1 d . . . . .
N1 N 0.4356(3) 0.8317(3) 0.2333(7) 0.0286(11) Uani 1 1 d . . . . .
N3 N 0.6320(3) 0.6302(3) 0.3427(8) 0.0361(13) Uani 1 1 d . . . . .
N4 N 0.4741(3) 0.5845(3) 0.2604(8) 0.0429(14) Uani 1 1 d . . . . .
C10 C 0.4790(4) 0.6773(3) 0.2611(8) 0.0270(13) Uani 1 1 d . . . . .
C5 C 0.2999(4) 0.7279(4) 0.1543(8) 0.0241(13) Uani 1 1 d . . . . .
C8 C 0.4069(4) 0.7447(3) 0.2164(8) 0.0239(13) Uani 1 1 d . . . . .
C11 C 0.5759(4) 0.7073(3) 0.3139(8) 0.0266(13) Uani 1 1 d . . . . .
C4 C 0.2336(4) 0.8014(4) 0.1177(8) 0.0286(14) Uani 1 1 d . . . . .
H4 H 0.2579 0.8617 0.1301 0.034 Uiso 1 1 calc R . . . .
C9 C 0.5324(4) 0.8499(4) 0.2878(8) 0.0312(14) Uani 1 1 d . . . . .
H9 H 0.5494 0.9123 0.2962 0.037 Uiso 1 1 calc R . . . .
C2 C 0.0950(4) 0.6998(4) 0.0397(8) 0.0351(15) Uani 1 1 d . . . . .
C3 C 0.1341(4) 0.7860(4) 0.0641(8) 0.0333(15) Uani 1 1 d . . . . .
C6 C 0.2602(4) 0.6410(4) 0.1257(8) 0.0305(14) Uani 1 1 d . . . . .
H6 H 0.3033 0.5903 0.1438 0.037 Uiso 1 1 calc R . . . .
C7 C 0.1603(4) 0.6268(4) 0.0719(8) 0.0366(15) Uani 1 1 d . . . . .
H7 H 0.1355 0.5666 0.0566 0.044 Uiso 1 1 calc R . . . .
C1 C -0.0161(4) 0.6817(4) -0.0173(9) 0.0389(16) Uani 1 1 d . . . . .
H1A H -0.0490 0.7109 0.0782 0.058 Uiso 1 1 calc GR . . . .
H1B H -0.0281 0.6163 -0.0177 0.058 Uiso 1 1 calc GR . . . .
H1C H -0.0423 0.7064 -0.1487 0.058 Uiso 1 1 calc GR . . . .
C12 C 0.5672(4) 0.5605(4) 0.3090(10) 0.0489(19) Uani 1 1 d . . . . .
H12 H 0.5875 0.4989 0.3197 0.059 Uiso 1 1 calc R . . . .
C13 C 0.7399(4) 0.6258(4) 0.3948(10) 0.0427(17) Uani 1 1 d . . . . .
H13 H 0.7653 0.6893 0.4131 0.051 Uiso 1 1 calc R . . . .
C14 C 0.7738(5) 0.5756(5) 0.5899(9) 0.0537(19) Uani 1 1 d . . . . .
H14A H 0.7463 0.6054 0.6925 0.081 Uiso 1 1 calc GR . . . .
H14B H 0.8458 0.5765 0.6268 0.081 Uiso 1 1 calc GR . . . .
H14C H 0.7508 0.5127 0.5752 0.081 Uiso 1 1 calc GR . . . .
C15 C 0.7783(5) 0.5844(5) 0.2268(10) 0.059(2) Uani 1 1 d . . . . .
H15A H 0.7603 0.5201 0.2147 0.089 Uiso 1 1 calc GR . . . .
H15B H 0.8501 0.5903 0.2525 0.089 Uiso 1 1 calc GR . . . .
H15C H 0.7494 0.6158 0.1042 0.089 Uiso 1 1 calc GR . . . .


_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
Cl1 C3 1.745(6) . ?
N2 C11 1.332(7) . ?
N2 C9 1.323(7) . ?
N1 C8 1.342(7) . ?
N1 C9 1.345(7) . ?
N3 C11 1.369(6) . ?
N3 C12 1.355(7) . ?
N3 C13 1.467(7) . ?
N4 C10 1.372(7) . ?
N4 C12 1.314(7) . ?
C10 C8 1.399(7) . ?
C10 C11 1.392(7) . ?
C5 C8 1.479(7) . ?
C5 C4 1.411(7) . ?
C5 C6 1.394(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.372(7) . ?
C9 H9 0.9500 . ?
C2 C3 1.380(8) . ?
C2 C7 1.396(8) . ?
C2 C1 1.535(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(8) . ?
C7 H7 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.531(9) . ?
C13 C15 1.511(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C9 N2 C11 110.9(5) . . ?
C8 N1 C9 118.5(5) . . ?
C11 N3 C13 126.4(5) . . ?
C12 N3 C11 105.6(4) . . ?
C12 N3 C13 128.0(5) . . ?
C12 N4 C10 102.9(4) . . ?
N4 C10 C8 132.6(5) . . ?
N4 C10 C11 111.2(5) . . ?
C11 C10 C8 116.2(5) . . ?
C4 C5 C8 120.1(5) . . ?
C6 C5 C8 122.6(5) . . ?
C6 C5 C4 117.2(5) . . ?
N1 C8 C10 118.3(5) . . ?
N1 C8 C5 116.6(4) . . ?
C10 C8 C5 125.0(5) . . ?
N2 C11 N3 127.5(5) . . ?
N2 C11 C10 127.2(5) . . ?
N3 C11 C10 105.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
N2 C9 N1 128.9(5) . . ?
N2 C9 H9 115.5 . . ?
N1 C9 H9 115.5 . . ?
C3 C2 C7 117.8(5) . . ?
C3 C2 C1 122.7(5) . . ?
C7 C2 C1 119.4(5) . . ?
C4 C3 Cl1 117.6(5) . . ?
C4 C3 C2 122.2(5) . . ?
C2 C3 Cl1 120.1(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.7(5) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.7(5) . . ?
C6 C7 H7 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C12 H12 122.5 . . ?
N4 C12 N3 114.9(5) . . ?
N4 C12 H12 122.5 . . ?
N3 C13 H13 107.8 . . ?
N3 C13 C14 110.5(5) . . ?
N3 C13 C15 109.5(6) . . ?
C14 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
C15 C13 C14 113.3(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3-hexane'
####################################################################### 
# 
# 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_mo_2017932_0m
_database_code_depnum_ccdc_archive 'CCDC 1586058'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;
_audit_creation_date             2017-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F6 N2 O8 Ru2'
_chemical_formula_sum            'C12 H6 F6 N2 O8 Ru2'
_chemical_formula_weight         622.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 1 21/c 1'
_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                   14.2908(11)
_cell_length_b                   8.8234(7)
_cell_length_c                   15.2802(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.799(2)
_cell_angle_gamma                90
_cell_volume                     1886.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.146
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0881 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.8219. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16475
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         1.456
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3519
_reflns_number_total             4342
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+1.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0821
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F0AA-C12 \\sim F4-C12 \\sim F6-C12 \\sim F1AA-C12 \\sim F5-C12 \\sim F2AA-C12
 with sigma of 0.02
 F6-C12 \\sim F1AA-C12 \\sim F5-C12 \\sim F2AA-C12 \\sim F4-C12 \\sim F0AA-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq, Uanis(F1AA) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F2AA)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F0AA) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: F6(0.5) F5(0.5) F4(0.5) F1AA(0.5) F0AA(0.5) F2AA(0.5)
5.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ru2 Ru 0.20332(2) 0.42951(3) 0.72109(2) 0.02120(9) Uani 1 1 d . . . . .
Ru1 Ru 0.26839(2) 0.24506(3) 0.85996(2) 0.02257(9) Uani 1 1 d . . . . .
O2 O 0.1510(2) 0.2237(3) 0.65333(18) 0.0324(7) Uani 1 1 d . . . . .
O4 O 0.33386(18) 0.3700(3) 0.68103(17) 0.0287(6) Uani 1 1 d . . . . .
O1 O 0.21459(19) 0.0715(3) 0.76753(18) 0.0315(6) Uani 1 1 d . . . . .
O3 O 0.39301(18) 0.2309(3) 0.80308(19) 0.0338(7) Uani 1 1 d . . . . .
F2 F 0.1224(2) -0.1575(3) 0.6740(2) 0.0597(8) Uani 1 1 d . . . . .
O6 O 0.2823(2) 0.7006(4) 0.8286(2) 0.0453(8) Uani 1 1 d . . . . .
F3 F 0.0810(3) -0.0193(3) 0.5617(2) 0.0822(12) Uani 1 1 d . . . . .
N1 N 0.1614(2) 0.5296(4) 0.5874(2) 0.0276(7) Uani 1 1 d . . . . .
O7 O 0.0244(2) 0.5262(4) 0.7761(2) 0.0561(10) Uani 1 1 d . . . . .
N2 N 0.3319(2) 0.0583(4) 0.9433(2) 0.0283(7) Uani 1 1 d . . . . .
F6 F 0.4796(10) 0.2819(13) 0.6101(6) 0.070(3) Uani 0.5 1 d D U P A 1
F5 F 0.5565(9) 0.3531(13) 0.7367(9) 0.083(4) Uani 0.5 1 d D U P A 1
O8 O 0.0859(2) 0.2536(4) 0.9266(3) 0.0569(10) Uani 1 1 d . . . . .
F4 F 0.5213(8) 0.1275(10) 0.7142(7) 0.058(3) Uani 0.5 1 d D U P A 1
C7 C 0.2540(3) 0.5981(5) 0.7858(3) 0.0285(9) Uani 1 1 d . . . . .
F1 F 0.2269(3) -0.0877(5) 0.6044(3) 0.1106(17) Uani 1 1 d . . . . .
C9 C 0.1733(3) 0.0998(4) 0.6895(3) 0.0262(8) Uani 1 1 d . . . . .
C3 C 0.3623(3) -0.0365(5) 0.9898(3) 0.0271(9) Uani 1 1 d . . . . .
C11 C 0.3950(3) 0.2906(4) 0.7301(3) 0.0251(8) Uani 1 1 d . . . . .
O5 O 0.3560(3) 0.4800(5) 0.9909(3) 0.0816(14) Uani 1 1 d . . . . .
C5 C 0.1564(3) 0.2530(5) 0.9023(3) 0.0340(10) Uani 1 1 d . . . . .
C1 C 0.1319(3) 0.5845(4) 0.5202(3) 0.0282(9) Uani 1 1 d . . . . .
C8 C 0.0918(3) 0.4826(5) 0.7549(3) 0.0321(9) Uani 1 1 d . . . . .
C12 C 0.4877(3) 0.2625(5) 0.6960(3) 0.0375(11) Uani 1 1 d D . . . .
C2 C 0.0960(3) 0.6557(6) 0.4340(3) 0.0461(12) Uani 1 1 d . . . . .
H2A H 0.1153 0.5956 0.3867 0.069 Uiso 1 1 calc GR . . . .
H2B H 0.1224 0.7582 0.4340 0.069 Uiso 1 1 calc GR . . . .
H2C H 0.0261 0.6612 0.4232 0.069 Uiso 1 1 calc GR . . . .
C4 C 0.4009(3) -0.1583(5) 1.0509(3) 0.0408(11) Uani 1 1 d . . . . .
H4A H 0.3999 -0.2533 1.0175 0.061 Uiso 1 1 calc GR . . . .
H4B H 0.3619 -0.1695 1.0963 0.061 Uiso 1 1 calc GR . . . .
H4C H 0.4668 -0.1342 1.0801 0.061 Uiso 1 1 calc GR . . . .
C10 C 0.1504(3) -0.0418(5) 0.6308(3) 0.0402(11) Uani 1 1 d . . . . .
C6 C 0.3213(4) 0.3910(5) 0.9399(3) 0.0431(11) Uani 1 1 d . . . . .
F1AA F 0.4946(9) 0.3438(11) 0.6272(6) 0.059(3) Uani 0.5 1 d D U P A 2
F0AA F 0.4981(10) 0.1188(12) 0.6805(8) 0.082(4) Uani 0.5 1 d D U P A 2
F2AA F 0.5616(7) 0.3057(14) 0.7583(7) 0.064(3) Uani 0.5 1 d D U 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
Ru2 Ru1 2.6849(4) . ?
Ru2 O2 2.148(3) . ?
Ru2 O4 2.144(2) . ?
Ru2 N1 2.193(3) . ?
Ru2 C7 1.850(4) . ?
Ru2 C8 1.833(4) . ?
Ru1 O1 2.118(3) . ?
Ru1 O3 2.139(3) . ?
Ru1 N2 2.165(3) . ?
Ru1 C5 1.846(4) . ?
Ru1 C6 1.828(5) . ?
O2 C9 1.236(5) . ?
O4 C11 1.244(4) . ?
O1 C9 1.243(5) . ?
O3 C11 1.238(5) . ?
F2 C10 1.321(5) . ?
O6 C7 1.142(5) . ?
F3 C10 1.308(5) . ?
N1 C1 1.136(5) . ?
O7 C8 1.145(5) . ?
N2 C3 1.126(5) . ?
F6 C12 1.306(9) . ?
F5 C12 1.320(10) . ?
O8 C5 1.142(5) . ?
F4 C12 1.294(9) . ?
F1 C10 1.304(5) . ?
C9 C10 1.534(6) . ?
C3 C4 1.456(6) . ?
C11 C12 1.539(5) . ?
O5 C6 1.146(5) . ?
C1 C2 1.455(6) . ?
C12 F1AA 1.294(9) . ?
C12 F0AA 1.304(10) . ?
C12 F2AA 1.325(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
O2 Ru2 Ru1 84.18(7) . . ?
O2 Ru2 N1 83.66(11) . . ?
O4 Ru2 Ru1 84.04(7) . . ?
O4 Ru2 O2 83.83(11) . . ?
O4 Ru2 N1 85.47(11) . . ?
N1 Ru2 Ru1 164.71(9) . . ?
C7 Ru2 Ru1 91.74(12) . . ?
C7 Ru2 O2 175.77(14) . . ?
C7 Ru2 O4 94.66(14) . . ?
C7 Ru2 N1 100.18(15) . . ?
C8 Ru2 Ru1 96.48(13) . . ?
C8 Ru2 O2 96.59(16) . . ?
C8 Ru2 O4 179.36(15) . . ?
C8 Ru2 N1 94.09(15) . . ?
C8 Ru2 C7 84.95(18) . . ?
O1 Ru1 Ru2 83.77(7) . . ?
O1 Ru1 O3 84.59(11) . . ?
O1 Ru1 N2 83.88(11) . . ?
O3 Ru1 Ru2 84.08(7) . . ?
O3 Ru1 N2 84.88(11) . . ?
N2 Ru1 Ru2 164.13(9) . . ?
C5 Ru1 Ru2 93.95(12) . . ?
C5 Ru1 O1 92.22(16) . . ?
C5 Ru1 O3 176.41(15) . . ?
C5 Ru1 N2 96.44(15) . . ?
C6 Ru1 Ru2 97.48(14) . . ?
C6 Ru1 O1 176.93(18) . . ?
C6 Ru1 O3 92.74(18) . . ?
C6 Ru1 N2 94.39(17) . . ?
C6 Ru1 C5 90.5(2) . . ?
C9 O2 Ru2 119.9(2) . . ?
C11 O4 Ru2 120.7(2) . . ?
C9 O1 Ru1 122.0(3) . . ?
C11 O3 Ru1 121.0(2) . . ?
C1 N1 Ru2 173.8(3) . . ?
C3 N2 Ru1 176.5(3) . . ?
O6 C7 Ru2 176.6(4) . . ?
O2 C9 O1 129.4(4) . . ?
O2 C9 C10 117.0(4) . . ?
O1 C9 C10 113.5(4) . . ?
N2 C3 C4 179.1(5) . . ?
O4 C11 C12 115.7(3) . . ?
O3 C11 O4 129.8(4) . . ?
O3 C11 C12 114.6(3) . . ?
O8 C5 Ru1 177.6(4) . . ?
N1 C1 C2 179.0(5) . . ?
O7 C8 Ru2 175.1(4) . . ?
F6 C12 F5 107.3(9) . . ?
F6 C12 C11 114.5(7) . . ?
F5 C12 C11 110.6(7) . . ?
F4 C12 F6 106.8(8) . . ?
F4 C12 F5 104.4(8) . . ?
F4 C12 C11 112.6(6) . . ?
F1AA C12 C11 113.6(6) . . ?
F1AA C12 F0AA 111.1(8) . . ?
F1AA C12 F2AA 104.0(8) . . ?
F0AA C12 C11 110.9(8) . . ?
F0AA C12 F2AA 107.9(8) . . ?
F2AA C12 C11 109.0(7) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
F2 C10 C9 112.8(4) . . ?
F3 C10 F2 105.3(4) . . ?
F3 C10 C9 112.6(4) . . ?
F1 C10 F2 105.9(4) . . ?
F1 C10 F3 110.0(4) . . ?
F1 C10 C9 110.0(4) . . ?
O5 C6 Ru1 178.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH-MeCN'
