# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_dk150821
_database_code_depnum_ccdc_archive 'CCDC 1473442'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H46 Mo2 N2 Ni2 O16'
_chemical_formula_sum            'C16 H46 Mo2 N2 Ni2 O16'
_chemical_formula_weight         831.85

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0683(6)
_cell_length_b                   10.1464(5)
_cell_length_c                   12.6315(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.8930(10)
_cell_angle_gamma                90
_cell_volume                     1545.88(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8780
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.54

_exptl_crystal_description       prism
_exptl_crystal_colour_primary    green
_exptl_crystal_colour_modifier   light
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    2.059
_shelx_estimated_absorpt_T_min   0.493
_shelx_estimated_absorpt_T_max   0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20049
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4500
_reflns_number_gt                4001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Sheldrick, 2010)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4500
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0502
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.57610(2) 0.30427(2) 0.84903(2) 0.01398(4) Uani 1 1 d . . . . .
Ni1 Ni 0.54670(2) 0.60992(2) 0.93060(2) 0.01242(5) Uani 1 1 d . . . . .
O1 O 0.53373(12) 0.34144(13) 0.72157(10) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.69288(11) 0.21238(13) 0.83474(11) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.65892(9) 0.47503(12) 0.87897(9) 0.0153(2) Uani 1 1 d . . . . .
O4 O 0.45117(9) 0.44458(11) 0.91045(9) 0.0135(2) Uani 1 1 d . . . . .
O5 O 0.45782(11) 0.16925(12) 0.86150(10) 0.0202(3) Uani 1 1 d . . . . .
O6 O 0.57755(10) 0.28050(12) 1.01346(9) 0.0157(2) Uani 1 1 d . . . . .
O7 O 0.65703(11) 0.76041(13) 0.97083(11) 0.0202(3) Uani 1 1 d . . . . .
H7 H 0.630(2) 0.796(2) 1.019(2) 0.033(7) Uiso 1 1 d . . . . .
O8 O 0.51583(11) 0.67936(13) 0.78063(10) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.52723(13) 0.68638(16) 0.60325(12) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.77550(15) 0.4871(2) 0.89277(17) 0.0259(4) Uani 1 1 d . . . . .
H3A H 0.7978 0.5776 0.8766 0.039 Uiso 1 1 calc R U . . .
H3B H 0.8119 0.4260 0.8450 0.039 Uiso 1 1 calc R U . . .
H3C H 0.7974 0.4661 0.9662 0.039 Uiso 1 1 calc R U . . .
C4 C 0.34816(14) 0.46266(18) 0.85281(14) 0.0188(3) Uani 1 1 d . . . . .
H4A H 0.3009 0.3853 0.8624 0.028 Uiso 1 1 calc R U . . .
H4B H 0.3623 0.4739 0.7774 0.028 Uiso 1 1 calc R U . . .
H4C H 0.3107 0.5412 0.8792 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3976(2) 0.1158(2) 0.77352(17) 0.0341(5) Uani 1 1 d . . . . .
H5A H 0.3290 0.0756 0.7975 0.051 Uiso 1 1 calc R U . . .
H5B H 0.4426 0.0487 0.7394 0.051 Uiso 1 1 calc R U . . .
H5C H 0.3795 0.1862 0.7227 0.051 Uiso 1 1 calc R U . . .
C6 C 0.61302(17) 0.16364(18) 1.06543(15) 0.0233(4) Uani 1 1 d . . . . .
H6A H 0.6732 0.1235 1.0264 0.035 Uiso 1 1 calc R U . . .
H6B H 0.5508 0.1018 1.0682 0.035 Uiso 1 1 calc R U . . .
H6C H 0.6396 0.1847 1.1376 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6925(2) 0.8574(2) 0.89662(17) 0.0311(5) Uani 1 1 d . . . . .
H7A H 0.7435 0.9193 0.9326 0.047 Uiso 1 1 calc R U . . .
H7B H 0.6279 0.9053 0.8677 0.047 Uiso 1 1 calc R U . . .
H7C H 0.7305 0.8137 0.8389 0.047 Uiso 1 1 calc R U . . .
C8 C 0.55966(15) 0.64384(17) 0.69833(13) 0.0172(3) Uani 1 1 d . . . . .
H8A H 0.6195 0.5831 0.7036 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5857(2) 0.6499(2) 0.50896(15) 0.0333(5) Uani 1 1 d . . . . .
H9A H 0.5325 0.6171 0.4549 0.050 Uiso 1 1 calc R U . . .
H9B H 0.6398 0.5807 0.5267 0.050 Uiso 1 1 calc R U . . .
H9C H 0.6242 0.7271 0.4817 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4379(2) 0.7816(3) 0.59030(19) 0.0421(6) Uani 1 1 d . . . . .
H10A H 0.3845 0.7506 0.5357 0.063 Uiso 1 1 calc R U . . .
H10B H 0.4684 0.8668 0.5690 0.063 Uiso 1 1 calc R U . . .
H10C H 0.4005 0.7918 0.6575 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 O2 1.7044(13) . ?
Mo1 O1 1.7151(13) . ?
Mo1 O5 1.9885(13) . ?
Mo1 O3 2.0295(12) . ?
Mo1 O6 2.0905(12) . ?
Mo1 O4 2.2314(12) . ?
Ni1 O6 2.0134(12) 3_667 ?
Ni1 O8 2.0438(12) . ?
Ni1 O4 2.0467(12) . ?
Ni1 O3 2.0472(12) . ?
Ni1 O7 2.0779(13) . ?
Ni1 O4 2.0818(11) 3_667 ?
O3 C3 1.417(2) . ?
O4 C4 1.432(2) . ?
O4 Ni1 2.0818(11) 3_667 ?
O5 C5 1.415(2) . ?
O6 C6 1.415(2) . ?
O6 Ni1 2.0135(12) 3_667 ?
O7 C7 1.434(2) . ?
O7 H7 0.79(3) . ?
O8 C8 1.236(2) . ?
N1 C8 1.323(2) . ?
N1 C9 1.452(3) . ?
N1 C10 1.453(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O2 Mo1 O1 104.05(7) . . ?
O2 Mo1 O5 103.29(6) . . ?
O1 Mo1 O5 91.91(6) . . ?
O2 Mo1 O3 94.75(6) . . ?
O1 Mo1 O3 96.71(6) . . ?
O5 Mo1 O3 157.49(5) . . ?
O2 Mo1 O6 93.57(6) . . ?
O1 Mo1 O6 161.90(6) . . ?
O5 Mo1 O6 79.88(5) . . ?
O3 Mo1 O6 85.73(5) . . ?
O2 Mo1 O4 163.02(6) . . ?
O1 Mo1 O4 90.12(6) . . ?
O5 Mo1 O4 85.24(5) . . ?
O3 Mo1 O4 74.02(4) . . ?
O6 Mo1 O4 73.24(4) . . ?
O6 Ni1 O8 91.13(5) 3_667 . ?
O6 Ni1 O4 94.20(5) 3_667 . ?
O8 Ni1 O4 94.74(5) . . ?
O6 Ni1 O3 171.55(5) 3_667 . ?
O8 Ni1 O3 92.15(5) . . ?
O4 Ni1 O3 77.77(5) . . ?
O6 Ni1 O7 89.26(5) 3_667 . ?
O8 Ni1 O7 93.96(5) . . ?
O4 Ni1 O7 170.57(5) . . ?
O3 Ni1 O7 98.28(5) . . ?
O6 Ni1 O4 78.10(5) 3_667 3_667 ?
O8 Ni1 O4 168.96(5) . 3_667 ?
O4 Ni1 O4 83.75(5) . 3_667 ?
O3 Ni1 O4 98.19(5) . 3_667 ?
O7 Ni1 O4 88.39(5) . 3_667 ?
C3 O3 Mo1 125.27(11) . . ?
C3 O3 Ni1 124.57(11) . . ?
Mo1 O3 Ni1 107.65(5) . . ?
C4 O4 Ni1 115.74(10) . . ?
C4 O4 Ni1 120.48(10) . 3_667 ?
Ni1 O4 Ni1 96.25(5) . 3_667 ?
C4 O4 Mo1 119.36(10) . . ?
Ni1 O4 Mo1 100.48(5) . . ?
Ni1 O4 Mo1 100.31(5) 3_667 . ?
C5 O5 Mo1 123.57(12) . . ?
C6 O6 Ni1 121.16(11) . 3_667 ?
C6 O6 Mo1 123.38(11) . . ?
Ni1 O6 Mo1 107.64(5) 3_667 . ?
C7 O7 Ni1 123.17(12) . . ?
C7 O7 H7 109.6(18) . . ?
Ni1 O7 H7 104.0(19) . . ?
C8 O8 Ni1 127.54(12) . . ?
C8 N1 C9 121.60(17) . . ?
C8 N1 C10 121.01(17) . . ?
C9 N1 C10 117.14(17) . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O6 C6 H6A 109.5 . . ?
O6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O6 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O7 C7 H7A 109.5 . . ?
O7 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O7 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 N1 123.13(17) . . ?
O8 C8 H8A 118.4 . . ?
N1 C8 H8A 118.4 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O8 C8 N1 173.78(13) . . . . ?
C9 N1 C8 O8 175.55(18) . . . . ?
C10 N1 C8 O8 1.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O5 0.79(3) 1.90(3) 2.6665(19) 163(3) 3_667

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.080



