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In the title structure, [Ni(C11H15N2O)(C11H16N2O)]ClO4, there are two independent ion pairs in the asymmetric unit. In each cation, the NiII atom is six-coordinated in a slightly distorted octa­hedral geometry by two phenolate O atoms, two imine N atoms and two amine N atoms from two Schiff base ligands, in one of which the phenolate O atom is protonated. In the crystal structure, anions and cations are linked through inter­molecular O—H...O, N—H...O and weak C—H...O hydrogen bonds, forming one-dimensional chains containing hydrogen-bonded cation dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017302/lh2064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017302/lh2064Isup2.hkl
Contains datablock I

CCDC reference: 613761

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.057
  • wR factor = 0.156
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CL1 .. 2.92 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. CL2 .. 2.95 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported N2 .. CL1 .. 3.81 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported N8 .. CL2 .. 3.84 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998)'; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Bis{2-[2-(ethylamino)ethyliminomethyl]phenolato}nickel(II) perchlorate top
Crystal data top
[Ni(C11H15N2O)(C11H16N2O)]ClO4Z = 4
Mr = 541.67F(000) = 1136
Triclinic, P1Dx = 1.455 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.813 (2) ÅCell parameters from 3297 reflections
b = 13.850 (2) Åθ = 2.4–24.3°
c = 13.979 (2) ŵ = 0.94 mm1
α = 100.24 (2)°T = 298 K
β = 106.14 (2)°Block, green
γ = 98.45 (2)°0.25 × 0.10 × 0.10 mm
V = 2472.9 (7) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
9586 independent reflections
Radiation source: fine-focus sealed tube6741 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1617
Tmin = 0.800, Tmax = 0.912k = 1717
19417 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.076P)2 + 0.0425P]
where P = (Fo2 + 2Fc2)/3
9586 reflections(Δ/σ)max < 0.001
663 parametersΔρmax = 0.81 e Å3
74 restraintsΔρmin = 0.62 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.60434 (4)0.19091 (4)0.31777 (4)0.03301 (15)
Ni20.90966 (4)0.29019 (4)0.18112 (4)0.03409 (15)
Cl10.27062 (14)0.11242 (13)0.39909 (15)0.0895 (5)
Cl20.79467 (10)0.63561 (10)0.95224 (11)0.0655 (4)
O10.71604 (19)0.3228 (2)0.3371 (2)0.0379 (6)
O20.67468 (19)0.12334 (18)0.21491 (19)0.0354 (6)
O30.7507 (2)0.22541 (19)0.1176 (2)0.0359 (6)
O40.88671 (19)0.30452 (19)0.32474 (19)0.0360 (6)
O50.3672 (3)0.0878 (3)0.4421 (4)0.1052 (15)
O60.1938 (4)0.0252 (4)0.3666 (4)0.1190 (17)
O70.2452 (4)0.1795 (4)0.4726 (5)0.148 (2)
O80.2785 (5)0.1588 (5)0.3220 (5)0.179 (3)
O90.7082 (8)0.5732 (8)0.8715 (9)0.140 (4)0.67 (2)
O100.8731 (7)0.5826 (7)0.9650 (11)0.092 (3)0.67 (2)
O120.7605 (16)0.6568 (6)1.0353 (11)0.138 (6)0.67 (2)
O9'0.6926 (7)0.6006 (19)0.929 (2)0.135 (11)0.33 (2)
O12'0.837 (2)0.6685 (12)1.0630 (7)0.102 (6)0.33 (2)
O10'0.848 (2)0.5622 (14)0.926 (2)0.111 (9)0.33 (2)
O110.8229 (3)0.7215 (3)0.9173 (4)0.1100 (16)
N10.5092 (2)0.2531 (3)0.2181 (2)0.0387 (8)
N20.4711 (3)0.0709 (3)0.2645 (3)0.0434 (8)
N30.6919 (2)0.1254 (2)0.4194 (2)0.0354 (7)
N40.5646 (3)0.2525 (3)0.4507 (3)0.0435 (8)
N50.8682 (3)0.4208 (2)0.1598 (3)0.0412 (8)
N61.0598 (3)0.3861 (3)0.2463 (3)0.0426 (8)
N70.9552 (2)0.1606 (2)0.2026 (3)0.0400 (8)
N80.9324 (3)0.2431 (3)0.0351 (3)0.0461 (9)
C10.6055 (3)0.4258 (3)0.2622 (3)0.0410 (10)
C20.7001 (3)0.4146 (3)0.3241 (3)0.0364 (9)
C30.7785 (3)0.4984 (3)0.3703 (3)0.0495 (11)
H30.84170.49090.41060.059*
C40.7652 (4)0.5926 (3)0.3581 (4)0.0605 (13)
H40.81850.64810.39070.073*
C50.6720 (4)0.6039 (4)0.2970 (4)0.0671 (15)
H50.66240.66690.28720.081*
C60.5950 (4)0.5224 (4)0.2515 (4)0.0551 (12)
H60.53220.53100.21140.066*
C70.5187 (3)0.3435 (3)0.2097 (3)0.0449 (11)
H70.46300.35870.16410.054*
C80.4112 (3)0.1850 (4)0.1596 (3)0.0525 (12)
H8A0.39010.19410.09010.063*
H8B0.35850.19990.19030.063*
C90.4223 (3)0.0790 (4)0.1584 (3)0.0541 (12)
H9A0.35510.03430.12990.065*
H9B0.46450.05980.11620.065*
C100.4816 (3)0.0326 (3)0.2721 (4)0.0584 (13)
H10A0.51950.03120.34220.070*
H10B0.52230.05530.22950.070*
C110.3812 (4)0.1081 (4)0.2408 (4)0.0739 (16)
H11A0.33600.08210.27520.111*
H11B0.39430.16960.25910.111*
H11C0.34940.12050.16810.111*
C120.7412 (3)0.0032 (3)0.3050 (3)0.0362 (9)
C130.7125 (3)0.0398 (3)0.2158 (3)0.0332 (9)
C140.7277 (3)0.0116 (3)0.1278 (3)0.0415 (10)
H140.71110.01270.06870.050*
C150.7669 (3)0.0979 (3)0.1261 (3)0.0489 (11)
H150.77570.13110.06620.059*
C160.7929 (3)0.1350 (3)0.2126 (4)0.0550 (12)
H160.81920.19310.21150.066*
C170.7794 (3)0.0854 (3)0.3003 (3)0.0472 (11)
H170.79610.11120.35850.057*
C180.7349 (3)0.0516 (3)0.4028 (3)0.0392 (9)
H180.76500.02650.45890.047*
C190.6878 (4)0.1582 (3)0.5232 (3)0.0504 (11)
H19A0.63860.10890.53640.060*
H19B0.75490.16370.57200.060*
C200.6577 (4)0.2546 (4)0.5359 (3)0.0647 (14)
H20A0.71360.30660.53730.078*
H20B0.64350.27000.60050.078*
C210.5319 (4)0.3480 (4)0.4615 (4)0.0654 (14)
H21A0.47460.34480.40140.078*
H21B0.58810.40000.46310.078*
C220.4996 (4)0.3783 (4)0.5559 (4)0.0725 (15)
H22A0.45290.32280.56190.109*
H22B0.46610.43400.55010.109*
H22C0.55940.39740.61560.109*
C230.6872 (3)0.3637 (3)0.0586 (3)0.0391 (9)
C240.6747 (3)0.2616 (3)0.0610 (3)0.0343 (9)
C250.5815 (3)0.1981 (3)0.0045 (3)0.0433 (10)
H250.57280.13030.00480.052*
C260.5012 (3)0.2329 (4)0.0522 (3)0.0544 (12)
H260.43940.18850.09020.065*
C270.5121 (4)0.3327 (4)0.0529 (4)0.0616 (14)
H270.45750.35650.09010.074*
C280.6033 (3)0.3968 (4)0.0014 (3)0.0541 (12)
H280.61020.46430.00040.065*
C290.7811 (3)0.4382 (3)0.1130 (3)0.0440 (10)
H290.77770.50490.11390.053*
C300.9556 (4)0.5064 (3)0.2028 (4)0.0635 (14)
H30A0.93280.56440.23210.076*
H30B0.98190.52250.14870.076*
C311.0381 (4)0.4832 (4)0.2823 (4)0.0721 (15)
H31A1.10000.53470.30040.086*
H31B1.01730.48270.34310.086*
C321.1361 (3)0.3596 (4)0.3290 (4)0.0687 (15)
H32A1.14200.29100.30570.082*
H32B1.11040.36170.38700.082*
C331.2419 (4)0.4255 (4)0.3648 (4)0.0821 (18)
H33A1.26530.43040.30690.123*
H33B1.28860.39710.41100.123*
H33C1.23950.49110.39920.123*
C340.9668 (3)0.1726 (3)0.3815 (3)0.0389 (9)
C350.9259 (3)0.2594 (3)0.3990 (3)0.0356 (9)
C360.9243 (3)0.2973 (3)0.4978 (3)0.0448 (10)
H360.90000.35580.51130.054*
C370.9575 (3)0.2503 (4)0.5755 (3)0.0518 (12)
H370.95520.27710.64050.062*
C380.9943 (4)0.1637 (4)0.5584 (4)0.0557 (12)
H381.01480.13060.61050.067*
C391.0000 (3)0.1273 (3)0.4620 (3)0.0480 (11)
H391.02720.07030.45080.058*
C400.9753 (3)0.1271 (3)0.2836 (3)0.0426 (10)
H400.99790.06690.27920.051*
C410.9763 (4)0.1066 (3)0.1129 (4)0.0577 (13)
H41A0.95800.03490.10660.069*
H41B1.04920.12420.12100.069*
C420.9151 (4)0.1334 (3)0.0186 (3)0.0566 (13)
H42A0.93620.10560.03930.068*
H42B0.84240.10570.00370.068*
C430.8728 (4)0.2776 (4)0.0532 (3)0.0604 (13)
H43A0.88590.35030.03550.073*
H43B0.80000.25330.06460.073*
C440.8958 (4)0.2445 (5)0.1526 (4)0.0851 (19)
H44A0.96830.26460.14150.128*
H44B0.85830.27500.20350.128*
H44C0.87540.17280.17550.128*
H80.9993 (13)0.265 (4)0.042 (4)0.080*
H20.426 (3)0.080 (4)0.298 (3)0.080*
H6A1.082 (4)0.398 (4)0.194 (3)0.080*
H4A0.518 (3)0.203 (3)0.455 (4)0.080*
H3A0.730 (4)0.190 (3)0.154 (3)0.080*
H10.7755 (19)0.316 (4)0.333 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0329 (3)0.0372 (3)0.0311 (3)0.0083 (2)0.0110 (2)0.0111 (2)
Ni20.0338 (3)0.0336 (3)0.0348 (3)0.0044 (2)0.0124 (2)0.0070 (2)
Cl10.0968 (12)0.0888 (11)0.1418 (15)0.0513 (10)0.0861 (12)0.0712 (11)
Cl20.0591 (8)0.0723 (9)0.0889 (10)0.0243 (7)0.0416 (8)0.0402 (8)
O10.0324 (15)0.0366 (15)0.0491 (17)0.0135 (12)0.0135 (13)0.0145 (13)
O20.0431 (16)0.0347 (15)0.0352 (15)0.0141 (12)0.0151 (12)0.0155 (12)
O30.0350 (15)0.0365 (15)0.0397 (16)0.0055 (12)0.0117 (12)0.0187 (12)
O40.0380 (15)0.0412 (15)0.0344 (15)0.0168 (12)0.0132 (12)0.0130 (12)
O50.079 (3)0.101 (3)0.167 (5)0.036 (3)0.064 (3)0.053 (3)
O60.093 (3)0.101 (4)0.149 (5)0.030 (3)0.005 (3)0.038 (3)
O70.145 (5)0.129 (4)0.219 (6)0.061 (4)0.122 (5)0.035 (4)
O80.212 (6)0.230 (6)0.219 (6)0.120 (5)0.149 (5)0.175 (5)
O90.077 (5)0.177 (8)0.145 (8)0.011 (5)0.020 (5)0.039 (7)
O100.065 (4)0.096 (5)0.134 (9)0.037 (4)0.030 (5)0.056 (5)
O120.252 (18)0.075 (6)0.180 (9)0.063 (8)0.183 (11)0.051 (6)
O9'0.040 (6)0.18 (2)0.23 (2)0.026 (8)0.042 (9)0.152 (19)
O12'0.132 (11)0.092 (9)0.090 (6)0.033 (8)0.044 (7)0.022 (6)
O10'0.17 (2)0.117 (13)0.100 (15)0.092 (16)0.079 (16)0.041 (11)
O110.097 (3)0.114 (3)0.179 (5)0.044 (3)0.081 (3)0.105 (3)
N10.0325 (18)0.050 (2)0.0349 (19)0.0097 (16)0.0099 (15)0.0130 (16)
N20.041 (2)0.048 (2)0.041 (2)0.0023 (17)0.0157 (16)0.0115 (17)
N30.0418 (19)0.0352 (18)0.0314 (18)0.0098 (15)0.0125 (15)0.0098 (14)
N40.045 (2)0.052 (2)0.038 (2)0.0175 (17)0.0156 (17)0.0111 (17)
N50.042 (2)0.0350 (19)0.043 (2)0.0004 (16)0.0102 (17)0.0118 (16)
N60.0354 (19)0.043 (2)0.046 (2)0.0034 (16)0.0121 (17)0.0057 (17)
N70.0389 (19)0.0358 (19)0.048 (2)0.0079 (15)0.0197 (17)0.0059 (16)
N80.044 (2)0.048 (2)0.045 (2)0.0002 (17)0.0214 (18)0.0031 (17)
C10.046 (2)0.047 (2)0.043 (2)0.021 (2)0.021 (2)0.020 (2)
C20.042 (2)0.036 (2)0.041 (2)0.0151 (19)0.0212 (19)0.0141 (18)
C30.051 (3)0.046 (3)0.054 (3)0.014 (2)0.018 (2)0.011 (2)
C40.070 (3)0.039 (3)0.077 (4)0.010 (2)0.030 (3)0.014 (2)
C50.095 (4)0.042 (3)0.086 (4)0.029 (3)0.044 (3)0.029 (3)
C60.066 (3)0.060 (3)0.055 (3)0.033 (3)0.023 (3)0.030 (2)
C70.044 (3)0.063 (3)0.040 (2)0.025 (2)0.018 (2)0.025 (2)
C80.035 (2)0.077 (3)0.042 (3)0.007 (2)0.004 (2)0.021 (2)
C90.046 (3)0.066 (3)0.037 (3)0.006 (2)0.005 (2)0.005 (2)
C100.050 (3)0.047 (3)0.070 (3)0.005 (2)0.016 (2)0.010 (2)
C110.074 (4)0.065 (3)0.073 (4)0.016 (3)0.029 (3)0.010 (3)
C120.034 (2)0.036 (2)0.040 (2)0.0090 (17)0.0105 (18)0.0132 (18)
C130.029 (2)0.031 (2)0.039 (2)0.0029 (16)0.0122 (17)0.0074 (17)
C140.042 (2)0.040 (2)0.040 (2)0.0034 (19)0.0115 (19)0.0059 (19)
C150.044 (3)0.046 (3)0.050 (3)0.009 (2)0.013 (2)0.003 (2)
C160.054 (3)0.044 (3)0.065 (3)0.023 (2)0.012 (2)0.006 (2)
C170.048 (3)0.042 (2)0.054 (3)0.018 (2)0.010 (2)0.020 (2)
C180.044 (2)0.040 (2)0.038 (2)0.0111 (19)0.0133 (19)0.0180 (19)
C190.061 (3)0.060 (3)0.035 (2)0.022 (2)0.015 (2)0.015 (2)
C200.082 (4)0.072 (3)0.042 (3)0.024 (3)0.021 (3)0.010 (3)
C210.087 (4)0.060 (3)0.060 (3)0.026 (3)0.037 (3)0.008 (3)
C220.090 (4)0.075 (4)0.072 (4)0.038 (3)0.047 (3)0.016 (3)
C230.037 (2)0.044 (2)0.040 (2)0.0083 (19)0.0119 (19)0.0203 (19)
C240.034 (2)0.041 (2)0.032 (2)0.0085 (18)0.0137 (17)0.0133 (17)
C250.042 (2)0.046 (2)0.042 (2)0.004 (2)0.014 (2)0.012 (2)
C260.041 (3)0.071 (3)0.048 (3)0.002 (2)0.008 (2)0.021 (2)
C270.044 (3)0.080 (4)0.064 (3)0.018 (3)0.008 (2)0.038 (3)
C280.052 (3)0.058 (3)0.056 (3)0.014 (2)0.012 (2)0.030 (2)
C290.058 (3)0.033 (2)0.047 (3)0.010 (2)0.020 (2)0.0180 (19)
C300.060 (3)0.036 (3)0.077 (4)0.002 (2)0.001 (3)0.013 (2)
C310.063 (3)0.051 (3)0.084 (4)0.003 (3)0.006 (3)0.005 (3)
C320.043 (3)0.073 (4)0.075 (4)0.007 (3)0.000 (3)0.023 (3)
C330.050 (3)0.086 (4)0.090 (4)0.004 (3)0.002 (3)0.022 (3)
C340.032 (2)0.039 (2)0.048 (3)0.0071 (18)0.0121 (19)0.0157 (19)
C350.026 (2)0.040 (2)0.040 (2)0.0051 (17)0.0071 (17)0.0125 (18)
C360.044 (2)0.051 (3)0.040 (2)0.017 (2)0.010 (2)0.011 (2)
C370.047 (3)0.065 (3)0.036 (2)0.007 (2)0.006 (2)0.008 (2)
C380.056 (3)0.059 (3)0.052 (3)0.014 (2)0.006 (2)0.029 (2)
C390.042 (2)0.045 (3)0.059 (3)0.017 (2)0.010 (2)0.021 (2)
C400.035 (2)0.035 (2)0.063 (3)0.0145 (18)0.020 (2)0.011 (2)
C410.068 (3)0.051 (3)0.064 (3)0.018 (2)0.037 (3)0.005 (2)
C420.065 (3)0.053 (3)0.050 (3)0.003 (2)0.030 (3)0.004 (2)
C430.061 (3)0.076 (4)0.038 (3)0.003 (3)0.017 (2)0.010 (2)
C440.089 (4)0.115 (5)0.047 (3)0.004 (4)0.032 (3)0.012 (3)
Geometric parameters (Å, º) top
Ni1—N32.031 (3)C11—H11C0.9600
Ni1—N12.037 (3)C12—C171.403 (5)
Ni1—O22.110 (3)C12—C131.407 (5)
Ni1—O12.134 (3)C12—C181.444 (5)
Ni1—N22.146 (4)C13—C141.393 (5)
Ni1—N42.150 (3)C14—C151.382 (6)
Ni2—N52.022 (3)C14—H140.9300
Ni2—N72.031 (3)C15—C161.374 (6)
Ni2—O42.098 (3)C15—H150.9300
Ni2—O32.114 (3)C16—C171.369 (6)
Ni2—N62.146 (3)C16—H160.9300
Ni2—N82.153 (3)C17—H170.9300
Cl1—O81.369 (5)C18—H180.9300
Cl1—O61.397 (5)C19—C201.451 (6)
Cl1—O71.414 (5)C19—H19A0.9700
Cl1—O51.420 (4)C19—H19B0.9700
Cl2—O9'1.347 (8)C20—H20A0.9700
Cl2—O121.372 (5)C20—H20B0.9700
Cl2—O101.385 (6)C21—C221.518 (6)
Cl2—O10'1.394 (9)C21—H21A0.9700
Cl2—O111.408 (3)C21—H21B0.9700
Cl2—O91.430 (7)C22—H22A0.9600
Cl2—O12'1.454 (9)C22—H22B0.9600
O1—C21.358 (4)C22—H22C0.9600
O1—H10.86 (3)C23—C281.401 (5)
O2—C131.338 (4)C23—C241.408 (5)
O3—C241.346 (4)C23—C291.451 (6)
O3—H3A0.84 (4)C24—C251.382 (5)
O4—C351.334 (4)C25—C261.376 (6)
N1—C71.270 (5)C25—H250.9300
N1—C81.459 (5)C26—C271.371 (6)
N2—C91.480 (5)C26—H260.9300
N2—C101.481 (6)C27—C281.361 (6)
N2—H20.89 (4)C27—H270.9300
N3—C181.274 (5)C28—H280.9300
N3—C191.461 (5)C29—H290.9300
N4—C211.456 (6)C30—C311.473 (7)
N4—C201.482 (6)C30—H30A0.9700
N4—H4A0.89 (4)C30—H30B0.9700
N5—C291.280 (5)C31—H31A0.9700
N5—C301.464 (5)C31—H31B0.9700
N6—C311.454 (6)C32—C331.503 (6)
N6—C321.473 (6)C32—H32A0.9700
N6—H6A0.90 (5)C32—H32B0.9700
N7—C401.274 (5)C33—H33A0.9600
N7—C411.467 (5)C33—H33B0.9600
N8—C421.469 (6)C33—H33C0.9600
N8—C431.479 (6)C34—C391.385 (6)
N8—H80.90 (3)C34—C351.414 (5)
C1—C61.396 (6)C34—C401.446 (6)
C1—C21.399 (5)C35—C361.395 (5)
C1—C71.445 (6)C36—C371.369 (6)
C2—C31.382 (6)C36—H360.9300
C3—C41.377 (6)C37—C381.378 (6)
C3—H30.9300C37—H370.9300
C4—C51.380 (7)C38—C391.379 (6)
C4—H40.9300C38—H380.9300
C5—C61.351 (7)C39—H390.9300
C5—H50.9300C40—H400.9300
C6—H60.9300C41—C421.496 (6)
C7—H70.9300C41—H41A0.9700
C8—C91.497 (6)C41—H41B0.9700
C8—H8A0.9700C42—H42A0.9700
C8—H8B0.9700C42—H42B0.9700
C9—H9A0.9700C43—C441.518 (6)
C9—H9B0.9700C43—H43A0.9700
C10—C111.511 (6)C43—H43B0.9700
C10—H10A0.9700C44—H44A0.9600
C10—H10B0.9700C44—H44B0.9600
C11—H11A0.9600C44—H44C0.9600
C11—H11B0.9600
N3—Ni1—N1176.64 (12)H11A—C11—H11B109.5
N3—Ni1—O284.89 (11)C10—C11—H11C109.5
N1—Ni1—O297.26 (11)H11A—C11—H11C109.5
N3—Ni1—O198.53 (12)H11B—C11—H11C109.5
N1—Ni1—O184.27 (12)C17—C12—C13118.8 (4)
O2—Ni1—O184.79 (10)C17—C12—C18117.0 (4)
N3—Ni1—N295.92 (14)C13—C12—C18124.1 (3)
N1—Ni1—N281.40 (14)O2—C13—C14120.2 (3)
O2—Ni1—N293.31 (12)O2—C13—C12121.8 (3)
O1—Ni1—N2165.19 (12)C14—C13—C12118.1 (4)
N3—Ni1—N481.40 (13)C15—C14—C13121.6 (4)
N1—Ni1—N496.64 (13)C15—C14—H14119.2
O2—Ni1—N4165.62 (12)C13—C14—H14119.2
O1—Ni1—N492.94 (13)C16—C15—C14120.4 (4)
N2—Ni1—N492.41 (14)C16—C15—H15119.8
N5—Ni2—N7178.45 (12)C14—C15—H15119.8
N5—Ni2—O494.04 (12)C17—C16—C15119.2 (4)
N7—Ni2—O486.61 (12)C17—C16—H16120.4
N5—Ni2—O385.69 (12)C15—C16—H16120.4
N7—Ni2—O395.75 (12)C16—C17—C12121.9 (4)
O4—Ni2—O386.69 (10)C16—C17—H17119.1
N5—Ni2—N682.08 (14)C12—C17—H17119.1
N7—Ni2—N696.50 (14)N3—C18—C12125.9 (4)
O4—Ni2—N691.87 (12)N3—C18—H18117.0
O3—Ni2—N6167.56 (12)C12—C18—H18117.0
N5—Ni2—N897.46 (14)C20—C19—N3110.4 (4)
N7—Ni2—N881.97 (14)C20—C19—H19A109.6
O4—Ni2—N8167.99 (12)N3—C19—H19A109.6
O3—Ni2—N890.74 (12)C20—C19—H19B109.6
N6—Ni2—N893.11 (13)N3—C19—H19B109.6
O8—Cl1—O6113.6 (4)H19A—C19—H19B108.1
O8—Cl1—O7108.2 (4)C19—C20—N4110.2 (4)
O6—Cl1—O7107.1 (3)C19—C20—H20A109.6
O8—Cl1—O5107.8 (3)N4—C20—H20A109.6
O6—Cl1—O5109.0 (3)C19—C20—H20B109.6
O7—Cl1—O5111.2 (3)N4—C20—H20B109.6
O9'—Cl2—O1267.8 (9)H20A—C20—H20B108.1
O9'—Cl2—O10128.6 (11)N4—C21—C22115.0 (4)
O12—Cl2—O10115.0 (6)N4—C21—H21A108.5
O9'—Cl2—O10'113.4 (9)C22—C21—H21A108.5
O12—Cl2—O10'130.0 (9)N4—C21—H21B108.5
O9'—Cl2—O11115.6 (7)C22—C21—H21B108.5
O12—Cl2—O11112.7 (4)H21A—C21—H21B107.5
O10—Cl2—O11109.8 (5)C21—C22—H22A109.5
O10'—Cl2—O11110.5 (9)C21—C22—H22B109.5
O12—Cl2—O9105.8 (6)H22A—C22—H22B109.5
O10—Cl2—O9106.8 (6)C21—C22—H22C109.5
O10'—Cl2—O984.8 (12)H22A—C22—H22C109.5
O11—Cl2—O9106.1 (5)H22B—C22—H22C109.5
O9'—Cl2—O12'107.5 (8)C28—C23—C24118.3 (4)
O10—Cl2—O12'82.8 (9)C28—C23—C29117.3 (4)
O10'—Cl2—O12'104.8 (8)C24—C23—C29124.4 (4)
O11—Cl2—O12'103.9 (7)O3—C24—C25120.0 (4)
O9—Cl2—O12'142.7 (7)O3—C24—C23121.5 (3)
C2—O1—Ni1128.4 (2)C25—C24—C23118.5 (4)
C2—O1—H1110 (3)C26—C25—C24121.6 (4)
Ni1—O1—H1118 (3)C26—C25—H25119.2
C13—O2—Ni1127.6 (2)C24—C25—H25119.2
C24—O3—Ni2129.0 (2)C27—C26—C25120.1 (4)
C24—O3—H3A112 (3)C27—C26—H26120.0
Ni2—O3—H3A112 (3)C25—C26—H26120.0
C35—O4—Ni2128.0 (2)C28—C27—C26119.6 (4)
C7—N1—C8117.2 (4)C28—C27—H27120.2
C7—N1—Ni1129.1 (3)C26—C27—H27120.2
C8—N1—Ni1113.1 (3)C27—C28—C23121.9 (4)
C9—N2—C10113.1 (4)C27—C28—H28119.1
C9—N2—Ni1102.8 (2)C23—C28—H28119.1
C10—N2—Ni1120.4 (3)N5—C29—C23126.1 (4)
C9—N2—H2107 (3)N5—C29—H29116.9
C10—N2—H2100 (3)C23—C29—H29116.9
Ni1—N2—H2113 (3)N5—C30—C31110.6 (4)
C18—N3—C19116.9 (3)N5—C30—H30A109.5
C18—N3—Ni1129.4 (3)C31—C30—H30A109.5
C19—N3—Ni1112.7 (2)N5—C30—H30B109.5
C21—N4—C20111.6 (4)C31—C30—H30B109.5
C21—N4—Ni1121.1 (3)H30A—C30—H30B108.1
C20—N4—Ni1102.7 (3)N6—C31—C30110.8 (4)
C21—N4—H4A112 (3)N6—C31—H31A109.5
C20—N4—H4A103 (3)C30—C31—H31A109.5
Ni1—N4—H4A104 (3)N6—C31—H31B109.5
C29—N5—C30117.3 (4)C30—C31—H31B109.5
C29—N5—Ni2130.5 (3)H31A—C31—H31B108.1
C30—N5—Ni2112.2 (3)N6—C32—C33115.4 (4)
C31—N6—C32110.4 (4)N6—C32—H32A108.4
C31—N6—Ni2103.3 (3)C33—C32—H32A108.4
C32—N6—Ni2118.6 (3)N6—C32—H32B108.4
C31—N6—H6A100 (3)C33—C32—H32B108.4
C32—N6—H6A115 (3)H32A—C32—H32B107.5
Ni2—N6—H6A107 (3)C32—C33—H33A109.5
C40—N7—C41118.4 (4)C32—C33—H33B109.5
C40—N7—Ni2129.0 (3)H33A—C33—H33B109.5
C41—N7—Ni2112.3 (3)C32—C33—H33C109.5
C42—N8—C43113.3 (4)H33A—C33—H33C109.5
C42—N8—Ni2103.5 (3)H33B—C33—H33C109.5
C43—N8—Ni2118.5 (3)C39—C34—C35118.6 (4)
C42—N8—H8107 (3)C39—C34—C40117.6 (4)
C43—N8—H8106 (3)C35—C34—C40123.7 (4)
Ni2—N8—H8108 (3)O4—C35—C36119.2 (4)
C6—C1—C2117.7 (4)O4—C35—C34122.7 (4)
C6—C1—C7118.5 (4)C36—C35—C34118.1 (4)
C2—C1—C7123.8 (4)C37—C36—C35121.6 (4)
O1—C2—C3120.1 (4)C37—C36—H36119.2
O1—C2—C1120.8 (4)C35—C36—H36119.2
C3—C2—C1119.1 (4)C36—C37—C38120.7 (4)
C4—C3—C2121.6 (4)C36—C37—H37119.6
C4—C3—H3119.2C38—C37—H37119.6
C2—C3—H3119.2C37—C38—C39118.5 (4)
C3—C4—C5119.5 (5)C37—C38—H38120.8
C3—C4—H4120.3C39—C38—H38120.8
C5—C4—H4120.3C38—C39—C34122.4 (4)
C6—C5—C4119.3 (4)C38—C39—H39118.8
C6—C5—H5120.3C34—C39—H39118.8
C4—C5—H5120.3N7—C40—C34127.0 (4)
C5—C6—C1122.8 (5)N7—C40—H40116.5
C5—C6—H6118.6C34—C40—H40116.5
C1—C6—H6118.6N7—C41—C42109.7 (4)
N1—C7—C1128.0 (4)N7—C41—H41A109.7
N1—C7—H7116.0C42—C41—H41A109.7
C1—C7—H7116.0N7—C41—H41B109.7
N1—C8—C9109.6 (3)C42—C41—H41B109.7
N1—C8—H8A109.8H41A—C41—H41B108.2
C9—C8—H8A109.8N8—C42—C41109.1 (4)
N1—C8—H8B109.8N8—C42—H42A109.9
C9—C8—H8B109.8C41—C42—H42A109.9
H8A—C8—H8B108.2N8—C42—H42B109.9
N2—C9—C8108.9 (4)C41—C42—H42B109.9
N2—C9—H9A109.9H42A—C42—H42B108.3
C8—C9—H9A109.9N8—C43—C44115.4 (4)
N2—C9—H9B109.9N8—C43—H43A108.4
C8—C9—H9B109.9C44—C43—H43A108.4
H9A—C9—H9B108.3N8—C43—H43B108.4
N2—C10—C11115.0 (4)C44—C43—H43B108.4
N2—C10—H10A108.5H43A—C43—H43B107.5
C11—C10—H10A108.5C43—C44—H44A109.5
N2—C10—H10B108.5C43—C44—H44B109.5
C11—C10—H10B108.5H44A—C44—H44B109.5
H10A—C10—H10B107.5C43—C44—H44C109.5
C10—C11—H11A109.5H44A—C44—H44C109.5
C10—C11—H11B109.5H44B—C44—H44C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.86 (3)1.60 (3)2.457 (4)180 (6)
O3—H3A···O20.84 (4)1.61 (5)2.448 (3)172 (5)
N4—H4A···O50.89 (4)2.37 (4)3.247 (6)167 (4)
N6—H6A···O10i0.90 (5)2.52 (2)3.411 (13)174 (5)
N6—H6A···O10i0.90 (5)2.27 (2)3.16 (2)174 (5)
N2—H2···Cl10.89 (4)2.92 (4)3.810 (4)177 (4)
N2—H2···O80.89 (4)2.52 (3)3.316 (7)149 (4)
N2—H2···O50.89 (4)2.36 (2)3.186 (6)154 (5)
N8—H8···Cl2i0.90 (3)2.95 (3)3.837 (4)170 (4)
N8—H8···O10i0.90 (3)2.57 (3)3.337 (10)143 (4)
N8—H8···O11i0.90 (3)2.33 (2)3.202 (5)162 (5)
C8—H8B···O80.972.503.325 (7)143
C18—H18···O6ii0.932.603.500 (7)163 (4)
C29—H29···O12iii0.932.54 (3)3.410 (7)155 (4)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z+1; (iii) x, y, z1.
 

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