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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_dicro
_database_code_depnum_ccdc_archive 'CCDC 1412848'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;
_audit_creation_date             2015-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C48 H32 Cr4 N8 Ni2 O14)'
_chemical_formula_sum            'C24 H16 Cr2 N4 Ni O7'
_chemical_formula_weight         635.12
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr -0.1635 2.4439 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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           23
_space_group_name_H-M_alt        'I 2 2 2'
_space_group_name_Hall           'I 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y, -z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   8.5465(9)
_cell_length_b                   15.9683(17)
_cell_length_c                   20.726(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2828.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.09
_cell_measurement_theta_min      3.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.403
_exptl_absorpt_correction_T_max  0.3175
_exptl_absorpt_correction_T_min  0.2135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1475
_diffrn_reflns_av_unetI/netI     0.2272
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4201
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        50.489
_diffrn_reflns_theta_max         50.489
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                719
_reflns_number_total             1489
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1489
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.0956
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          3.222
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1285P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2040
_refine_ls_wR_factor_ref         0.2406
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.48(5) 0.52(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N1-C4'
 2.4 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C5) = Uanis(C1) = Uanis(C2)
Uanis(C4') = Uanis(C5') = Uanis(C1') = Uanis(C2')
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C4')=Sof(H4')=Sof(C2')=Sof(H2')=Sof(C1')=Sof(H1')=Sof(C5')=Sof(H5')=1-
 FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C1)=Sof(H1)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C5(H5), C4(H4), C4'(H4'), C9(H9), C10(H10), C11(H11),
 C12(H12), C2'(H2'), C1'(H1'), C5'(H5')
7.b Fitted hexagon refined as free rotating group:
 C3(C2,C1,N1,C5,C4)
;
_atom_sites_solution_hydrogens   geom
_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
Ni1 Ni 0.5000 0.5000 0.2183(2) 0.0241(16) Uani 1 2 d S TU P . .
Cr1 Cr 0.1097(6) 0.4155(3) 0.2124(4) 0.088(2) Uani 1 1 d . U . . .
O1 O 0.2912(19) 0.4394(9) 0.2155(8) 0.048(4) Uani 1 1 d . U . . .
O2 O 0.070(3) 0.3355(15) 0.2494(13) 0.146(9) Uani 1 1 d . U . . .
N2 N 0.086(2) 0.9195(15) 0.6479(9) 0.043(6) Uani 1 1 d . U . . .
O3 O 0.067(3) 0.3949(16) 0.1359(14) 0.145(9) Uani 1 1 d . U . . .
C3 C 0.341(3) 0.6782(13) 0.3962(8) 0.038(5) Uani 1 1 d . U . . .
C2 C 0.259(4) 0.605(2) 0.3818(15) 0.037(11) Uani 0.37(4) 1 d G U . A 1
H2 H 0.1731 0.5890 0.4080 0.044 Uiso 0.37(4) 1 calc R . . A 1
C1 C 0.303(4) 0.5568(18) 0.3292(15) 0.037(11) Uani 0.37(4) 1 d G U . A 1
H1 H 0.2463 0.5071 0.3193 0.044 Uiso 0.37(4) 1 calc R . . A 1
N1 N 0.428(2) 0.5809(10) 0.2909(7) 0.033(4) Uani 1 1 d DG U . A .
C5 C 0.511(4) 0.6536(18) 0.3053(14) 0.037(11) Uani 0.37(4) 1 d G U . A 1
H5 H 0.5967 0.6701 0.2792 0.044 Uiso 0.37(4) 1 calc R . . A 1
C4 C 0.467(4) 0.7022(16) 0.3580(15) 0.037(11) Uani 0.37(4) 1 d G U . A 1
H4 H 0.5235 0.7519 0.3678 0.044 Uiso 0.37(4) 1 calc R . . A 1
O4 O 0.0000 0.5000 0.2412(14) 0.105(9) Uani 1 2 d S TU P . .
C4' C 0.473(6) 0.663(3) 0.387(2) 0.060(10) Uani 0.63(4) 1 d D U . A 23
H4' H 0.5503 0.6816 0.4169 0.072 Uiso 0.63(4) 1 calc R . . A 23
C6 C 0.297(3) 0.7266(17) 0.4575(12) 0.063(8) Uani 1 1 d . U . . .
C7 C 0.241(3) 0.7689(16) 0.4996(14) 0.058(7) Uani 1 1 d . U . . .
C8 C 0.196(3) 0.819(2) 0.5507(13) 0.058(8) Uani 1 1 d . U . . .
C9 C 0.105(4) 0.784(2) 0.6028(14) 0.093(11) Uani 1 1 d . U . . .
H9 H 0.0827 0.7254 0.6041 0.112 Uiso 1 1 calc R . . . .
C10 C 0.052(3) 0.8363(18) 0.6505(13) 0.061(9) Uani 1 1 d . U . . .
H10 H -0.0078 0.8146 0.6853 0.073 Uiso 1 1 calc R . . . .
C11 C 0.232(3) 0.8987(19) 0.5509(12) 0.064(9) Uani 1 1 d . U . . .
H11 H 0.2964 0.9215 0.5180 0.077 Uiso 1 1 calc R . . . .
C12 C 0.176(3) 0.9478(17) 0.5985(11) 0.055(8) Uani 1 1 d . U . . .
H12 H 0.2012 1.0057 0.5975 0.065 Uiso 1 1 calc R . . . .
C2' C 0.234(5) 0.658(3) 0.346(2) 0.060(10) Uani 0.63(4) 1 d . U . A 23
H2' H 0.1313 0.6808 0.3456 0.072 Uiso 0.63(4) 1 calc R . . A 23
C1' C 0.281(5) 0.607(3) 0.3008(19) 0.060(10) Uani 0.63(4) 1 d . U . A 23
H1' H 0.2039 0.5860 0.2721 0.072 Uiso 0.63(4) 1 calc R . . A 23
C5' C 0.521(6) 0.611(3) 0.3254(19) 0.060(10) Uani 0.63(4) 1 d . U . A 23
H5' H 0.6292 0.6031 0.3160 0.072 Uiso 0.63(4) 1 calc R . . A 23


_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
Ni1 O1 2.031(16) . ?
Ni1 O1 2.031(16) 2_665 ?
Ni1 N2 2.079(19) 5_544 ?
Ni1 N2 2.079(19) 6_564 ?
Ni1 N1 2.076(13) . ?
Ni1 N1 2.08(2) 2_665 ?
Cr1 O1 1.599(16) . ?
Cr1 O2 1.53(2) . ?
Cr1 O3 1.66(3) . ?
Cr1 O4 1.749(11) . ?
N2 Ni1 2.079(19) 5_455 ?
N2 C10 1.36(3) . ?
N2 C12 1.36(3) . ?
C3 C2 1.3900 . ?
C3 C4 1.3900 . ?
C3 C4' 1.16(5) . ?
C3 C6 1.54(3) . ?
C3 C2' 1.42(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.3900 . ?
C1 H1 0.9500 . ?
C1 N1 1.3900 . ?
N1 C5 1.3900 . ?
N1 C1' 1.34(4) . ?
N1 C5' 1.17(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
O4 Cr1 1.749(11) 2_565 ?
C4' H4' 0.9500 . ?
C4' C5' 1.59(5) . ?
C6 C7 1.20(3) . ?
C7 C8 1.38(3) . ?
C8 C9 1.45(4) . ?
C8 C11 1.31(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.37(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.35(3) . ?
C12 H12 0.9500 . ?
C2' H2' 0.9500 . ?
C2' C1' 1.31(4) . ?
C1' H1' 0.9500 . ?
C5' H5' 0.9500 . ?

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 Ni1 O1 176.7(9) . 2_665 ?
O1 Ni1 N2 88.0(8) . 6_564 ?
O1 Ni1 N2 89.7(7) 2_665 6_564 ?
O1 Ni1 N2 89.7(7) . 5_544 ?
O1 Ni1 N2 88.0(8) 2_665 5_544 ?
O1 Ni1 N1 93.3(6) . . ?
O1 Ni1 N1 89(3) . 2_665 ?
O1 Ni1 N1 93(3) 2_665 2_665 ?
O1 Ni1 N1 89.1(7) 2_665 . ?
N2 Ni1 N2 90.7(11) 5_544 6_564 ?
N1 Ni1 N2 176(2) 2_665 6_564 ?
N1 Ni1 N2 176.5(7) . 5_544 ?
N1 Ni1 N2 91.2(7) . 6_564 ?
N1 Ni1 N2 91.2(10) 2_665 5_544 ?
N1 Ni1 N1 87.1(13) . 2_665 ?
O1 Cr1 O3 107.4(12) . . ?
O1 Cr1 O4 108.8(6) . . ?
O2 Cr1 O1 113.3(12) . . ?
O2 Cr1 O3 105.4(14) . . ?
O2 Cr1 O4 110.8(11) . . ?
O3 Cr1 O4 111.1(13) . . ?
Cr1 O1 Ni1 165.4(9) . . ?
C10 N2 Ni1 120.1(18) . 5_455 ?
C12 N2 Ni1 121.5(19) . 5_455 ?
C12 N2 C10 118(2) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C6 118.2(18) . . ?
C4 C3 C6 121.6(18) . . ?
C4' C3 C6 118(3) . . ?
C4' C3 C2' 117(3) . . ?
C2' C3 C6 124(3) . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C1 H1 120.0 . . ?
N1 C1 C2 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 N1 Ni1 118.0(11) . . ?
C1 N1 C5 120.0 . . ?
C5 N1 Ni1 121.8(11) . . ?
C1' N1 Ni1 125(2) . . ?
C5' N1 Ni1 120(2) . . ?
C5' N1 C1' 115(3) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
Cr1 O4 Cr1 140.1(19) . 2_565 ?
C3 C4' H4' 120.3 . . ?
C3 C4' C5' 119(4) . . ?
C5' C4' H4' 120.3 . . ?
C7 C6 C3 169(3) . . ?
C6 C7 C8 173(3) . . ?
C7 C8 C9 120(3) . . ?
C11 C8 C7 120(3) . . ?
C11 C8 C9 120(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118(3) . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 120(3) . . ?
N2 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C11 H11 120.5 . . ?
C8 C11 C12 119(3) . . ?
C12 C11 H11 120.5 . . ?
N2 C12 H12 118.0 . . ?
C11 C12 N2 124(3) . . ?
C11 C12 H12 118.0 . . ?
C3 C2' H2' 121.1 . . ?
C1' C2' C3 118(4) . . ?
C1' C2' H2' 121.1 . . ?
N1 C1' H1' 116.8 . . ?
C2' C1' N1 126(4) . . ?
C2' C1' H1' 116.8 . . ?
N1 C5' C4' 122(4) . . ?
N1 C5' H5' 119.0 . . ?
C4' C5' H5' 119.0 . . ?

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 N2 C10 C9 178(2) 5_455 . . . ?
Ni1 N2 C12 C11 -179(2) 5_455 . . . ?
Ni1 N1 C5 C4 -174.2(11) . . . . ?
Ni1 N1 C1' C2' -180(3) . . . . ?
Ni1 N1 C5' C4' -172(2) . . . . ?
O1 Cr1 O4 Cr1 99.7(8) . . . 2_565 ?
O2 Cr1 O1 Ni1 -148(4) . . . . ?
O2 Cr1 O4 Cr1 -135.2(12) . . . 2_565 ?
O3 Cr1 O1 Ni1 96(4) . . . . ?
O3 Cr1 O4 Cr1 -18.3(10) . . . 2_565 ?
C3 C2 C1 N1 0.0 . . . . ?
C3 C4' C5' N1 -6(6) . . . . ?
C3 C2' C1' N1 -11(6) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C6 C7 -76(15) . . . . ?
C2 C1 N1 Ni1 174.4(11) . . . . ?
C2 C1 N1 C5 0.0 . . . . ?
C1 N1 C5 C4 0.0 . . . . ?
N1 C5 C4 C3 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C3 C6 C7 108(15) . . . . ?
O4 Cr1 O1 Ni1 -24(5) . . . . ?
C4' C3 C6 C7 153(14) . . . . ?
C4' C3 C2' C1' 16(6) . . . . ?
C6 C3 C2 C1 -176(2) . . . . ?
C6 C3 C4 C5 176(2) . . . . ?
C6 C3 C4' C5' 178(3) . . . . ?
C6 C3 C2' C1' -171(3) . . . . ?
C7 C8 C9 C10 -175(3) . . . . ?
C7 C8 C11 C12 174(2) . . . . ?
C8 C9 C10 N2 0(4) . . . . ?
C8 C11 C12 N2 1(4) . . . . ?
C9 C8 C11 C12 -3(4) . . . . ?
C10 N2 C12 C11 2(4) . . . . ?
C11 C8 C9 C10 3(4) . . . . ?
C12 N2 C10 C9 -2(4) . . . . ?
C2' C3 C4' C5' -8(5) . . . . ?
C2' C3 C6 C7 -20(16) . . . . ?
C1' N1 C5' C4' 12(5) . . . . ?
C5' N1 C1' C2' -3(6) . . . . ?


