# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global

_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_publ_contact_author_name        'Hong Zhang'
_publ_contact_author_address     
;
Department of Chemistry
Northeast Normal University
Changchun 130024
P.R.China
;
_publ_contact_author_email       zhangh@nenu.edu.cn
_publ_contact_author_phone       +86-431-85099370
_publ_contact_author_fax         +86-431-85099372

_publ_section_title              
;
?
;
loop_
_publ_author_name
'Sheng-qi Guo'
'Dian Tian'
'Hong Zhang'

data_complex-1
#TrackingRef '- ccdc_792136_cif.cif'

_database_code_depnum_ccdc_archive 'CCDC 792136'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 N4 Ni2 O11'
_chemical_formula_sum            'C20 H22 N4 Ni2 O11'
_chemical_formula_weight         617.84

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   12.1992(3)
_cell_length_b                   15.7190(5)
_cell_length_c                   25.8536(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4957.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      24.99

_exptl_crystal_description       triangular
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2512
_exptl_absorpt_coefficient_mu    1.585
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.602
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4416
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2083
_reflns_number_gt                1954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(16)
_refine_ls_number_reflns         2083
_refine_ls_number_parameters     168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.58704(19) 0.08195(16) 0.21747(9) 0.0281(6) Uani 1 1 d . . .
Ni1 Ni 0.46530(3) 0.10953(2) 0.269700(12) 0.01731(12) Uani 1 1 d . . .
O1 O 0.3457(2) 0.14867(14) 0.32269(9) 0.0253(6) Uani 1 1 d . . .
O1W O 0.5000 0.0000 0.31315(12) 0.0202(7) Uani 1 2 d S . .
H1WA H 0.5546 0.0104 0.3326 0.024 Uiso 0.50 1 d PR . .
O3 O 0.34227(18) 0.04766(15) 0.23090(10) 0.0273(6) Uani 1 1 d . . .
C4 C 0.0161(3) 0.1168(2) 0.41195(16) 0.0258(9) Uani 1 1 d . . .
H4 H -0.0449 0.0815 0.4137 0.031 Uiso 1 1 calc R . .
C2 C 0.2023(3) 0.1404(2) 0.38392(14) 0.0182(8) Uani 1 1 d . . .
C1 C 0.3001(3) 0.1039(2) 0.35567(13) 0.0180(7) Uani 1 1 d . . .
C6 C 0.1050(2) 0.2483(2) 0.43102(12) 0.0176(7) Uani 1 1 d . . .
H6 H 0.1033 0.3019 0.4461 0.021 Uiso 1 1 calc R . .
C7 C 0.2003(2) 0.2221(2) 0.40582(12) 0.0153(6) Uani 1 1 d . . .
N1 N 0.5734(3) 0.1896(2) 0.31016(14) 0.0439(9) Uani 1 1 d . . .
H1A H 0.5473 0.2007 0.3420 0.053 Uiso 1 1 calc R . .
H1B H 0.6397 0.1650 0.3132 0.053 Uiso 1 1 calc R . .
N2 N 0.4229(3) 0.2221(2) 0.23177(13) 0.0391(8) Uani 1 1 d . . .
H2A H 0.4487 0.2213 0.1992 0.047 Uiso 1 1 calc R . .
H2B H 0.3495 0.2274 0.2305 0.047 Uiso 1 1 calc R . .
C3 C 0.1100(3) 0.0893(2) 0.38697(14) 0.0261(8) Uani 1 1 d . . .
H3 H 0.1111 0.0355 0.3720 0.031 Uiso 1 1 calc R . .
C10 C 0.4704(4) 0.2934(3) 0.2602(2) 0.0555(14) Uani 1 1 d . . .
H10A H 0.4234 0.3084 0.2890 0.067 Uiso 1 1 calc R . .
H10B H 0.4764 0.3425 0.2376 0.067 Uiso 1 1 calc R . .
C9 C 0.5813(4) 0.2689(3) 0.2796(2) 0.0610(15) Uani 1 1 d . . .
H9A H 0.6306 0.2604 0.2506 0.073 Uiso 1 1 calc R . .
H9B H 0.6107 0.3142 0.3010 0.073 Uiso 1 1 calc R . .
C5 C 0.0125(3) 0.1969(2) 0.43433(13) 0.0211(7) Uani 1 1 d . . .
C8 C 0.3397(2) -0.0257(2) 0.21364(12) 0.0199(7) Uani 1 1 d . . .
O2 O 0.3265(2) 0.02927(17) 0.36755(11) 0.0383(7) Uani 1 1 d . . .
O2W O 0.7613(6) 0.1325(4) 0.3640(3) 0.125(2) Uani 1 1 d . . .
H2WC H 0.7837 0.1445 0.3942 0.150 Uiso 1 1 d R . .
H2WD H 0.7335 0.0829 0.3646 0.150 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0198(12) 0.0301(13) 0.0343(14) 0.0080(12) 0.0124(10) 0.0104(12)
Ni1 0.01328(18) 0.01899(19) 0.01965(19) -0.00008(18) 0.00209(16) 0.00031(17)
O1 0.0268(13) 0.0189(13) 0.0301(14) 0.0000(10) 0.0143(11) 0.0032(10)
O1W 0.0172(15) 0.0225(17) 0.0207(16) 0.000 0.000 0.0052(14)
O3 0.0183(12) 0.0251(13) 0.0386(14) -0.0100(11) -0.0108(10) 0.0018(10)
C4 0.018(2) 0.0232(19) 0.036(2) -0.0022(16) 0.0087(17) -0.0098(16)
C2 0.0178(17) 0.0192(18) 0.0177(17) 0.0035(13) -0.0007(13) 0.0007(14)
C1 0.0154(16) 0.0176(17) 0.0211(17) -0.0005(15) 0.0026(13) 0.0010(14)
C6 0.0173(15) 0.0161(15) 0.0195(15) 0.0010(13) 0.0018(13) 0.0003(14)
C7 0.0124(14) 0.0183(16) 0.0153(15) 0.0041(12) -0.0005(12) 0.0001(13)
N1 0.0403(19) 0.050(2) 0.042(2) -0.0056(18) -0.0032(17) -0.0168(18)
N2 0.042(2) 0.038(2) 0.0371(19) 0.0132(16) 0.0081(16) 0.0103(17)
C3 0.0220(18) 0.0220(19) 0.034(2) -0.0065(15) 0.0099(15) -0.0052(15)
C10 0.093(4) 0.0213(18) 0.052(3) 0.000(2) 0.015(3) 0.003(2)
C9 0.077(3) 0.034(2) 0.072(4) -0.010(2) 0.011(3) -0.034(3)
C5 0.0144(15) 0.0267(19) 0.0221(16) 0.0026(14) 0.0043(13) 0.0014(15)
C8 0.0115(15) 0.0275(18) 0.0206(16) 0.0018(15) -0.0015(12) -0.0013(14)
O2 0.0384(15) 0.0269(15) 0.0496(17) 0.0118(13) 0.0250(13) 0.0109(13)
O2W 0.130(4) 0.123(5) 0.121(5) 0.015(4) -0.047(4) -0.030(4)

_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
O4 C8 1.261(4) 2_655 ?
O4 Ni1 2.053(2) . ?
Ni1 O3 2.051(2) . ?
Ni1 N2 2.088(3) . ?
Ni1 O1 2.094(2) . ?
Ni1 O1W 2.0990(17) . ?
Ni1 N1 2.102(3) . ?
O1 C1 1.237(4) . ?
O1W Ni1 2.0990(17) 2_655 ?
O1W H1WA 0.8501 . ?
O3 C8 1.236(4) . ?
C4 C3 1.385(5) . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.385(5) . ?
C2 C7 1.405(5) . ?
C2 C1 1.512(5) . ?
C1 O2 1.255(4) . ?
C6 C5 1.390(5) . ?
C6 C7 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C7 1.497(6) 14 ?
N1 C9 1.479(6) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C10 1.460(6) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
C3 H3 0.9300 . ?
C10 C9 1.494(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 C8 1.521(4) 4 ?
C8 O4 1.261(4) 2_655 ?
C8 C5 1.521(4) 8_544 ?
O2W H2WC 0.8499 . ?
O2W H2WD 0.8501 . ?

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
C8 O4 Ni1 135.4(2) 2_655 . ?
O3 Ni1 O4 96.17(11) . . ?
O3 Ni1 N2 89.46(12) . . ?
O4 Ni1 N2 92.83(12) . . ?
O3 Ni1 O1 87.09(9) . . ?
O4 Ni1 O1 175.03(10) . . ?
N2 Ni1 O1 83.43(11) . . ?
O3 Ni1 O1W 91.17(8) . . ?
O4 Ni1 O1W 91.88(9) . . ?
N2 Ni1 O1W 175.15(12) . . ?
O1 Ni1 O1W 91.80(8) . . ?
O3 Ni1 N1 170.64(13) . . ?
O4 Ni1 N1 90.01(13) . . ?
N2 Ni1 N1 83.20(15) . . ?
O1 Ni1 N1 86.30(12) . . ?
O1W Ni1 N1 95.66(12) . . ?
C1 O1 Ni1 126.7(2) . . ?
Ni1 O1W Ni1 115.28(14) 2_655 . ?
Ni1 O1W H1WA 108.5 2_655 . ?
Ni1 O1W H1WA 108.5 . . ?
C8 O3 Ni1 129.6(2) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 116.7(3) . . ?
C7 C2 C1 123.7(3) . . ?
O1 C1 O2 125.8(3) . . ?
O1 C1 C2 118.2(3) . . ?
O2 C1 C2 116.0(3) . . ?
C5 C6 C7 122.3(3) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C2 118.2(3) . . ?
C6 C7 C7 120.2(3) . 14 ?
C2 C7 C7 121.5(3) . 14 ?
C9 N1 Ni1 106.3(3) . . ?
C9 N1 H1A 110.5 . . ?
Ni1 N1 H1A 110.5 . . ?
C9 N1 H1B 110.5 . . ?
Ni1 N1 H1B 110.5 . . ?
H1A N1 H1B 108.7 . . ?
C10 N2 Ni1 108.4(3) . . ?
C10 N2 H2A 110.0 . . ?
Ni1 N2 H2A 110.0 . . ?
C10 N2 H2B 110.0 . . ?
Ni1 N2 H2B 110.0 . . ?
H2A N2 H2B 108.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
N2 C10 C9 109.3(3) . . ?
N2 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
N1 C9 C10 109.7(4) . . ?
N1 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 C8 119.4(3) . 4 ?
C6 C5 C8 122.1(3) . 4 ?
O3 C8 O4 127.4(3) . 2_655 ?
O3 C8 C5 117.7(3) . 8_544 ?
O4 C8 C5 114.9(3) 2_655 8_544 ?
H2WC O2W H2WD 108.3 . . ?

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
C8 O4 Ni1 O3 -95.8(3) 2_655 . . . ?
C8 O4 Ni1 N2 174.4(3) 2_655 . . . ?
C8 O4 Ni1 O1 133.3(11) 2_655 . . . ?
C8 O4 Ni1 O1W -4.4(3) 2_655 . . . ?
C8 O4 Ni1 N1 91.2(3) 2_655 . . . ?
O3 Ni1 O1 C1 73.2(3) . . . . ?
O4 Ni1 O1 C1 -155.6(11) . . . . ?
N2 Ni1 O1 C1 163.0(3) . . . . ?
O1W Ni1 O1 C1 -17.8(3) . . . . ?
N1 Ni1 O1 C1 -113.4(3) . . . . ?
O3 Ni1 O1W Ni1 55.50(7) . . . 2_655 ?
O4 Ni1 O1W Ni1 -40.71(7) . . . 2_655 ?
N2 Ni1 O1W Ni1 152.9(13) . . . 2_655 ?
O1 Ni1 O1W Ni1 142.63(7) . . . 2_655 ?
N1 Ni1 O1W Ni1 -130.91(10) . . . 2_655 ?
O4 Ni1 O3 C8 50.8(3) . . . . ?
N2 Ni1 O3 C8 143.6(3) . . . . ?
O1 Ni1 O3 C8 -133.0(3) . . . . ?
O1W Ni1 O3 C8 -41.2(3) . . . . ?
N1 Ni1 O3 C8 -178.2(7) . . . . ?
Ni1 O1 C1 O2 9.0(5) . . . . ?
Ni1 O1 C1 C2 -169.6(2) . . . . ?
C3 C2 C1 O1 131.5(4) . . . . ?
C7 C2 C1 O1 -47.4(5) . . . . ?
C3 C2 C1 O2 -47.3(5) . . . . ?
C7 C2 C1 O2 133.9(4) . . . . ?
C5 C6 C7 C2 -1.1(5) . . . . ?
C5 C6 C7 C7 -176.7(3) . . . 14 ?
C3 C2 C7 C6 1.3(5) . . . . ?
C1 C2 C7 C6 -179.9(3) . . . . ?
C3 C2 C7 C7 176.9(3) . . . 14 ?
C1 C2 C7 C7 -4.3(4) . . . 14 ?
O3 Ni1 N1 C9 -54.8(9) . . . . ?
O4 Ni1 N1 C9 76.7(3) . . . . ?
N2 Ni1 N1 C9 -16.2(3) . . . . ?
O1 Ni1 N1 C9 -100.0(3) . . . . ?
O1W Ni1 N1 C9 168.6(3) . . . . ?
O3 Ni1 N2 C10 162.3(3) . . . . ?
O4 Ni1 N2 C10 -101.6(3) . . . . ?
O1 Ni1 N2 C10 75.2(3) . . . . ?
O1W Ni1 N2 C10 64.8(14) . . . . ?
N1 Ni1 N2 C10 -11.9(3) . . . . ?
C5 C4 C3 C2 0.3(6) . . . . ?
C7 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
Ni1 N2 C10 C9 38.0(4) . . . . ?
Ni1 N1 C9 C10 41.6(4) . . . . ?
N2 C10 C9 N1 -54.5(5) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C5 C8 -177.3(4) . . . 4 ?
C7 C6 C5 C4 0.4(5) . . . . ?
C7 C6 C5 C8 177.6(3) . . . 4 ?
Ni1 O3 C8 O4 2.6(5) . . . 2_655 ?
Ni1 O3 C8 C5 -177.6(2) . . . 8_544 ?

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
O2W H2WC O4 0.85 2.04 2.886(7) 177.7 3
O2W H2WD O2 0.85 1.91 2.760(7) 178.4 2_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.079