{2-[2-(Ethyl­amino)ethyl­imino­methyl]phenol}{2-[2-(ethyl­amino)ethyl­imino­methyl]phenolato}nickel(II) perchlorate

You, Z.-L.; Chi, J.-Y.

doi:10.1107/S1600536806017302

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{2-[2-(Ethylamino)ethyliminomethyl]phenol}{2-[2-(ethylamino)ethyliminomethyl]phenolato}nickel(II) perchlorate

Z.-L. You and J.-Y. Chi

In the title structure, [Ni(C₁₁H₁₅N₂O)(C₁₁H₁₆N₂O)]ClO₄, there are two independent ion pairs in the asymmetric unit. In each cation, the Ni^II 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017302/lh2064sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017302/lh2064Isup2.hkl Contains datablock I

CCDC reference: 613761

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (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)]ClO₄	Z = 4
M_r = 541.67	F(000) = 1136
Triclinic, P1	D_x = 1.455 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 13.813 (2) Å	Cell parameters from 3297 reflections
b = 13.850 (2) Å	θ = 2.4–24.3°
c = 13.979 (2) Å	µ = 0.94 mm⁻¹
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 tube	6741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.800, T_max = 0.912	k = −17→17
19417 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.076P)² + 0.0425P] where P = (F_o² + 2F_c²)/3
9586 reflections	(Δ/σ)_max < 0.001
663 parameters	Δρ_max = 0.81 e Å⁻³
74 restraints	Δρ_min = −0.62 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.60434 (4)	0.19091 (4)	0.31777 (4)	0.03301 (15)
Ni2	0.90966 (4)	0.29019 (4)	0.18112 (4)	0.03409 (15)
Cl1	0.27062 (14)	0.11242 (13)	0.39909 (15)	0.0895 (5)
Cl2	0.79467 (10)	0.63561 (10)	0.95224 (11)	0.0655 (4)
O1	0.71604 (19)	0.3228 (2)	0.3371 (2)	0.0379 (6)
O2	0.67468 (19)	0.12334 (18)	0.21491 (19)	0.0354 (6)
O3	0.7507 (2)	0.22541 (19)	0.1176 (2)	0.0359 (6)
O4	0.88671 (19)	0.30452 (19)	0.32474 (19)	0.0360 (6)
O5	0.3672 (3)	0.0878 (3)	0.4421 (4)	0.1052 (15)
O6	0.1938 (4)	0.0252 (4)	0.3666 (4)	0.1190 (17)
O7	0.2452 (4)	0.1795 (4)	0.4726 (5)	0.148 (2)
O8	0.2785 (5)	0.1588 (5)	0.3220 (5)	0.179 (3)
O9	0.7082 (8)	0.5732 (8)	0.8715 (9)	0.140 (4)	0.67 (2)
O10	0.8731 (7)	0.5826 (7)	0.9650 (11)	0.092 (3)	0.67 (2)
O12	0.7605 (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)
O11	0.8229 (3)	0.7215 (3)	0.9173 (4)	0.1100 (16)
N1	0.5092 (2)	0.2531 (3)	0.2181 (2)	0.0387 (8)
N2	0.4711 (3)	0.0709 (3)	0.2645 (3)	0.0434 (8)
N3	0.6919 (2)	0.1254 (2)	0.4194 (2)	0.0354 (7)
N4	0.5646 (3)	0.2525 (3)	0.4507 (3)	0.0435 (8)
N5	0.8682 (3)	0.4208 (2)	0.1598 (3)	0.0412 (8)
N6	1.0598 (3)	0.3861 (3)	0.2463 (3)	0.0426 (8)
N7	0.9552 (2)	0.1606 (2)	0.2026 (3)	0.0400 (8)
N8	0.9324 (3)	0.2431 (3)	0.0351 (3)	0.0461 (9)
C1	0.6055 (3)	0.4258 (3)	0.2622 (3)	0.0410 (10)
C2	0.7001 (3)	0.4146 (3)	0.3241 (3)	0.0364 (9)
C3	0.7785 (3)	0.4984 (3)	0.3703 (3)	0.0495 (11)
H3	0.8417	0.4909	0.4106	0.059*
C4	0.7652 (4)	0.5926 (3)	0.3581 (4)	0.0605 (13)
H4	0.8185	0.6481	0.3907	0.073*
C5	0.6720 (4)	0.6039 (4)	0.2970 (4)	0.0671 (15)
H5	0.6624	0.6669	0.2872	0.081*
C6	0.5950 (4)	0.5224 (4)	0.2515 (4)	0.0551 (12)
H6	0.5322	0.5310	0.2114	0.066*
C7	0.5187 (3)	0.3435 (3)	0.2097 (3)	0.0449 (11)
H7	0.4630	0.3587	0.1641	0.054*
C8	0.4112 (3)	0.1850 (4)	0.1596 (3)	0.0525 (12)
H8A	0.3901	0.1941	0.0901	0.063*
H8B	0.3585	0.1999	0.1903	0.063*
C9	0.4223 (3)	0.0790 (4)	0.1584 (3)	0.0541 (12)
H9A	0.3551	0.0343	0.1299	0.065*
H9B	0.4645	0.0598	0.1162	0.065*
C10	0.4816 (3)	−0.0326 (3)	0.2721 (4)	0.0584 (13)
H10A	0.5195	−0.0312	0.3422	0.070*
H10B	0.5223	−0.0553	0.2295	0.070*
C11	0.3812 (4)	−0.1081 (4)	0.2408 (4)	0.0739 (16)
H11A	0.3360	−0.0821	0.2752	0.111*
H11B	0.3943	−0.1696	0.2591	0.111*
H11C	0.3494	−0.1205	0.1681	0.111*
C12	0.7412 (3)	0.0032 (3)	0.3050 (3)	0.0362 (9)
C13	0.7125 (3)	0.0398 (3)	0.2158 (3)	0.0332 (9)
C14	0.7277 (3)	−0.0116 (3)	0.1278 (3)	0.0415 (10)
H14	0.7111	0.0127	0.0687	0.050*
C15	0.7669 (3)	−0.0979 (3)	0.1261 (3)	0.0489 (11)
H15	0.7757	−0.1311	0.0662	0.059*
C16	0.7929 (3)	−0.1350 (3)	0.2126 (4)	0.0550 (12)
H16	0.8192	−0.1931	0.2115	0.066*
C17	0.7794 (3)	−0.0854 (3)	0.3003 (3)	0.0472 (11)
H17	0.7961	−0.1112	0.3585	0.057*
C18	0.7349 (3)	0.0516 (3)	0.4028 (3)	0.0392 (9)
H18	0.7650	0.0265	0.4589	0.047*
C19	0.6878 (4)	0.1582 (3)	0.5232 (3)	0.0504 (11)
H19A	0.6386	0.1089	0.5364	0.060*
H19B	0.7549	0.1637	0.5720	0.060*
C20	0.6577 (4)	0.2546 (4)	0.5359 (3)	0.0647 (14)
H20A	0.7136	0.3066	0.5373	0.078*
H20B	0.6435	0.2700	0.6005	0.078*
C21	0.5319 (4)	0.3480 (4)	0.4615 (4)	0.0654 (14)
H21A	0.4746	0.3448	0.4014	0.078*
H21B	0.5881	0.4000	0.4631	0.078*
C22	0.4996 (4)	0.3783 (4)	0.5559 (4)	0.0725 (15)
H22A	0.4529	0.3228	0.5619	0.109*
H22B	0.4661	0.4340	0.5501	0.109*
H22C	0.5594	0.3974	0.6156	0.109*
C23	0.6872 (3)	0.3637 (3)	0.0586 (3)	0.0391 (9)
C24	0.6747 (3)	0.2616 (3)	0.0610 (3)	0.0343 (9)
C25	0.5815 (3)	0.1981 (3)	0.0045 (3)	0.0433 (10)
H25	0.5728	0.1303	0.0048	0.052*
C26	0.5012 (3)	0.2329 (4)	−0.0522 (3)	0.0544 (12)
H26	0.4394	0.1885	−0.0902	0.065*
C27	0.5121 (4)	0.3327 (4)	−0.0529 (4)	0.0616 (14)
H27	0.4575	0.3565	−0.0901	0.074*
C28	0.6033 (3)	0.3968 (4)	0.0014 (3)	0.0541 (12)
H28	0.6102	0.4643	0.0004	0.065*
C29	0.7811 (3)	0.4382 (3)	0.1130 (3)	0.0440 (10)
H29	0.7777	0.5049	0.1139	0.053*
C30	0.9556 (4)	0.5064 (3)	0.2028 (4)	0.0635 (14)
H30A	0.9328	0.5644	0.2321	0.076*
H30B	0.9819	0.5225	0.1487	0.076*
C31	1.0381 (4)	0.4832 (4)	0.2823 (4)	0.0721 (15)
H31A	1.1000	0.5347	0.3004	0.086*
H31B	1.0173	0.4827	0.3431	0.086*
C32	1.1361 (3)	0.3596 (4)	0.3290 (4)	0.0687 (15)
H32A	1.1420	0.2910	0.3057	0.082*
H32B	1.1104	0.3617	0.3870	0.082*
C33	1.2419 (4)	0.4255 (4)	0.3648 (4)	0.0821 (18)
H33A	1.2653	0.4304	0.3069	0.123*
H33B	1.2886	0.3971	0.4110	0.123*
H33C	1.2395	0.4911	0.3992	0.123*
C34	0.9668 (3)	0.1726 (3)	0.3815 (3)	0.0389 (9)
C35	0.9259 (3)	0.2594 (3)	0.3990 (3)	0.0356 (9)
C36	0.9243 (3)	0.2973 (3)	0.4978 (3)	0.0448 (10)
H36	0.9000	0.3558	0.5113	0.054*
C37	0.9575 (3)	0.2503 (4)	0.5755 (3)	0.0518 (12)
H37	0.9552	0.2771	0.6405	0.062*
C38	0.9943 (4)	0.1637 (4)	0.5584 (4)	0.0557 (12)
H38	1.0148	0.1306	0.6105	0.067*
C39	1.0000 (3)	0.1273 (3)	0.4620 (3)	0.0480 (11)
H39	1.0272	0.0703	0.4508	0.058*
C40	0.9753 (3)	0.1271 (3)	0.2836 (3)	0.0426 (10)
H40	0.9979	0.0669	0.2792	0.051*
C41	0.9763 (4)	0.1066 (3)	0.1129 (4)	0.0577 (13)
H41A	0.9580	0.0349	0.1066	0.069*
H41B	1.0492	0.1242	0.1210	0.069*
C42	0.9151 (4)	0.1334 (3)	0.0186 (3)	0.0566 (13)
H42A	0.9362	0.1056	−0.0393	0.068*
H42B	0.8424	0.1057	0.0037	0.068*
C43	0.8728 (4)	0.2776 (4)	−0.0532 (3)	0.0604 (13)
H43A	0.8859	0.3503	−0.0355	0.073*
H43B	0.8000	0.2533	−0.0646	0.073*
C44	0.8958 (4)	0.2445 (5)	−0.1526 (4)	0.0851 (19)
H44A	0.9683	0.2646	−0.1415	0.128*
H44B	0.8583	0.2750	−0.2035	0.128*
H44C	0.8754	0.1728	−0.1755	0.128*
H8	0.9993 (13)	0.265 (4)	0.042 (4)	0.080*
H2	0.426 (3)	0.080 (4)	0.298 (3)	0.080*
H6A	1.082 (4)	0.398 (4)	0.194 (3)	0.080*
H4A	0.518 (3)	0.203 (3)	0.455 (4)	0.080*
H3A	0.730 (4)	0.190 (3)	0.154 (3)	0.080*
H1	0.7755 (19)	0.316 (4)	0.333 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0329 (3)	0.0372 (3)	0.0311 (3)	0.0083 (2)	0.0110 (2)	0.0111 (2)
Ni2	0.0338 (3)	0.0336 (3)	0.0348 (3)	0.0044 (2)	0.0124 (2)	0.0070 (2)
Cl1	0.0968 (12)	0.0888 (11)	0.1418 (15)	0.0513 (10)	0.0861 (12)	0.0712 (11)
Cl2	0.0591 (8)	0.0723 (9)	0.0889 (10)	0.0243 (7)	0.0416 (8)	0.0402 (8)
O1	0.0324 (15)	0.0366 (15)	0.0491 (17)	0.0135 (12)	0.0135 (13)	0.0145 (13)
O2	0.0431 (16)	0.0347 (15)	0.0352 (15)	0.0141 (12)	0.0151 (12)	0.0155 (12)
O3	0.0350 (15)	0.0365 (15)	0.0397 (16)	0.0055 (12)	0.0117 (12)	0.0187 (12)
O4	0.0380 (15)	0.0412 (15)	0.0344 (15)	0.0168 (12)	0.0132 (12)	0.0130 (12)
O5	0.079 (3)	0.101 (3)	0.167 (5)	0.036 (3)	0.064 (3)	0.053 (3)
O6	0.093 (3)	0.101 (4)	0.149 (5)	0.030 (3)	0.005 (3)	0.038 (3)
O7	0.145 (5)	0.129 (4)	0.219 (6)	0.061 (4)	0.122 (5)	0.035 (4)
O8	0.212 (6)	0.230 (6)	0.219 (6)	0.120 (5)	0.149 (5)	0.175 (5)
O9	0.077 (5)	0.177 (8)	0.145 (8)	−0.011 (5)	0.020 (5)	0.039 (7)
O10	0.065 (4)	0.096 (5)	0.134 (9)	0.037 (4)	0.030 (5)	0.056 (5)
O12	0.252 (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)
O11	0.097 (3)	0.114 (3)	0.179 (5)	0.044 (3)	0.081 (3)	0.105 (3)
N1	0.0325 (18)	0.050 (2)	0.0349 (19)	0.0097 (16)	0.0099 (15)	0.0130 (16)
N2	0.041 (2)	0.048 (2)	0.041 (2)	0.0023 (17)	0.0157 (16)	0.0115 (17)
N3	0.0418 (19)	0.0352 (18)	0.0314 (18)	0.0098 (15)	0.0125 (15)	0.0098 (14)
N4	0.045 (2)	0.052 (2)	0.038 (2)	0.0175 (17)	0.0156 (17)	0.0111 (17)
N5	0.042 (2)	0.0350 (19)	0.043 (2)	0.0004 (16)	0.0102 (17)	0.0118 (16)
N6	0.0354 (19)	0.043 (2)	0.046 (2)	0.0034 (16)	0.0121 (17)	0.0057 (17)
N7	0.0389 (19)	0.0358 (19)	0.048 (2)	0.0079 (15)	0.0197 (17)	0.0059 (16)
N8	0.044 (2)	0.048 (2)	0.045 (2)	−0.0002 (17)	0.0214 (18)	0.0031 (17)
C1	0.046 (2)	0.047 (2)	0.043 (2)	0.021 (2)	0.021 (2)	0.020 (2)
C2	0.042 (2)	0.036 (2)	0.041 (2)	0.0151 (19)	0.0212 (19)	0.0141 (18)
C3	0.051 (3)	0.046 (3)	0.054 (3)	0.014 (2)	0.018 (2)	0.011 (2)
C4	0.070 (3)	0.039 (3)	0.077 (4)	0.010 (2)	0.030 (3)	0.014 (2)
C5	0.095 (4)	0.042 (3)	0.086 (4)	0.029 (3)	0.044 (3)	0.029 (3)
C6	0.066 (3)	0.060 (3)	0.055 (3)	0.033 (3)	0.023 (3)	0.030 (2)
C7	0.044 (3)	0.063 (3)	0.040 (2)	0.025 (2)	0.018 (2)	0.025 (2)
C8	0.035 (2)	0.077 (3)	0.042 (3)	0.007 (2)	0.004 (2)	0.021 (2)
C9	0.046 (3)	0.066 (3)	0.037 (3)	−0.006 (2)	0.005 (2)	0.005 (2)
C10	0.050 (3)	0.047 (3)	0.070 (3)	−0.005 (2)	0.016 (2)	0.010 (2)
C11	0.074 (4)	0.065 (3)	0.073 (4)	−0.016 (3)	0.029 (3)	0.010 (3)
C12	0.034 (2)	0.036 (2)	0.040 (2)	0.0090 (17)	0.0105 (18)	0.0132 (18)
C13	0.029 (2)	0.031 (2)	0.039 (2)	0.0029 (16)	0.0122 (17)	0.0074 (17)
C14	0.042 (2)	0.040 (2)	0.040 (2)	0.0034 (19)	0.0115 (19)	0.0059 (19)
C15	0.044 (3)	0.046 (3)	0.050 (3)	0.009 (2)	0.013 (2)	−0.003 (2)
C16	0.054 (3)	0.044 (3)	0.065 (3)	0.023 (2)	0.012 (2)	0.006 (2)
C17	0.048 (3)	0.042 (2)	0.054 (3)	0.018 (2)	0.010 (2)	0.020 (2)
C18	0.044 (2)	0.040 (2)	0.038 (2)	0.0111 (19)	0.0133 (19)	0.0180 (19)
C19	0.061 (3)	0.060 (3)	0.035 (2)	0.022 (2)	0.015 (2)	0.015 (2)
C20	0.082 (4)	0.072 (3)	0.042 (3)	0.024 (3)	0.021 (3)	0.010 (3)
C21	0.087 (4)	0.060 (3)	0.060 (3)	0.026 (3)	0.037 (3)	0.008 (3)
C22	0.090 (4)	0.075 (4)	0.072 (4)	0.038 (3)	0.047 (3)	0.016 (3)
C23	0.037 (2)	0.044 (2)	0.040 (2)	0.0083 (19)	0.0119 (19)	0.0203 (19)
C24	0.034 (2)	0.041 (2)	0.032 (2)	0.0085 (18)	0.0137 (17)	0.0133 (17)
C25	0.042 (2)	0.046 (2)	0.042 (2)	0.004 (2)	0.014 (2)	0.012 (2)
C26	0.041 (3)	0.071 (3)	0.048 (3)	0.002 (2)	0.008 (2)	0.021 (2)
C27	0.044 (3)	0.080 (4)	0.064 (3)	0.018 (3)	0.008 (2)	0.038 (3)
C28	0.052 (3)	0.058 (3)	0.056 (3)	0.014 (2)	0.012 (2)	0.030 (2)
C29	0.058 (3)	0.033 (2)	0.047 (3)	0.010 (2)	0.020 (2)	0.0180 (19)
C30	0.060 (3)	0.036 (3)	0.077 (4)	−0.002 (2)	−0.001 (3)	0.013 (2)
C31	0.063 (3)	0.051 (3)	0.084 (4)	0.003 (3)	0.006 (3)	0.005 (3)
C32	0.043 (3)	0.073 (4)	0.075 (4)	−0.007 (3)	0.000 (3)	0.023 (3)
C33	0.050 (3)	0.086 (4)	0.090 (4)	−0.004 (3)	−0.002 (3)	0.022 (3)
C34	0.032 (2)	0.039 (2)	0.048 (3)	0.0071 (18)	0.0121 (19)	0.0157 (19)
C35	0.026 (2)	0.040 (2)	0.040 (2)	0.0051 (17)	0.0071 (17)	0.0125 (18)
C36	0.044 (2)	0.051 (3)	0.040 (2)	0.017 (2)	0.010 (2)	0.011 (2)
C37	0.047 (3)	0.065 (3)	0.036 (2)	0.007 (2)	0.006 (2)	0.008 (2)
C38	0.056 (3)	0.059 (3)	0.052 (3)	0.014 (2)	0.006 (2)	0.029 (2)
C39	0.042 (2)	0.045 (3)	0.059 (3)	0.017 (2)	0.010 (2)	0.021 (2)
C40	0.035 (2)	0.035 (2)	0.063 (3)	0.0145 (18)	0.020 (2)	0.011 (2)
C41	0.068 (3)	0.051 (3)	0.064 (3)	0.018 (2)	0.037 (3)	0.005 (2)
C42	0.065 (3)	0.053 (3)	0.050 (3)	0.003 (2)	0.030 (3)	−0.004 (2)
C43	0.061 (3)	0.076 (4)	0.038 (3)	−0.003 (3)	0.017 (2)	0.010 (2)
C44	0.089 (4)	0.115 (5)	0.047 (3)	−0.004 (4)	0.032 (3)	0.012 (3)

Geometric parameters (Å, º) top

Ni1—N3	2.031 (3)	C11—H11C	0.9600
Ni1—N1	2.037 (3)	C12—C17	1.403 (5)
Ni1—O2	2.110 (3)	C12—C13	1.407 (5)
Ni1—O1	2.134 (3)	C12—C18	1.444 (5)
Ni1—N2	2.146 (4)	C13—C14	1.393 (5)
Ni1—N4	2.150 (3)	C14—C15	1.382 (6)
Ni2—N5	2.022 (3)	C14—H14	0.9300
Ni2—N7	2.031 (3)	C15—C16	1.374 (6)
Ni2—O4	2.098 (3)	C15—H15	0.9300
Ni2—O3	2.114 (3)	C16—C17	1.369 (6)
Ni2—N6	2.146 (3)	C16—H16	0.9300
Ni2—N8	2.153 (3)	C17—H17	0.9300
Cl1—O8	1.369 (5)	C18—H18	0.9300
Cl1—O6	1.397 (5)	C19—C20	1.451 (6)
Cl1—O7	1.414 (5)	C19—H19A	0.9700
Cl1—O5	1.420 (4)	C19—H19B	0.9700
Cl2—O9'	1.347 (8)	C20—H20A	0.9700
Cl2—O12	1.372 (5)	C20—H20B	0.9700
Cl2—O10	1.385 (6)	C21—C22	1.518 (6)
Cl2—O10'	1.394 (9)	C21—H21A	0.9700
Cl2—O11	1.408 (3)	C21—H21B	0.9700
Cl2—O9	1.430 (7)	C22—H22A	0.9600
Cl2—O12'	1.454 (9)	C22—H22B	0.9600
O1—C2	1.358 (4)	C22—H22C	0.9600
O1—H1	0.86 (3)	C23—C28	1.401 (5)
O2—C13	1.338 (4)	C23—C24	1.408 (5)
O3—C24	1.346 (4)	C23—C29	1.451 (6)
O3—H3A	0.84 (4)	C24—C25	1.382 (5)
O4—C35	1.334 (4)	C25—C26	1.376 (6)
N1—C7	1.270 (5)	C25—H25	0.9300
N1—C8	1.459 (5)	C26—C27	1.371 (6)
N2—C9	1.480 (5)	C26—H26	0.9300
N2—C10	1.481 (6)	C27—C28	1.361 (6)
N2—H2	0.89 (4)	C27—H27	0.9300
N3—C18	1.274 (5)	C28—H28	0.9300
N3—C19	1.461 (5)	C29—H29	0.9300
N4—C21	1.456 (6)	C30—C31	1.473 (7)
N4—C20	1.482 (6)	C30—H30A	0.9700
N4—H4A	0.89 (4)	C30—H30B	0.9700
N5—C29	1.280 (5)	C31—H31A	0.9700
N5—C30	1.464 (5)	C31—H31B	0.9700
N6—C31	1.454 (6)	C32—C33	1.503 (6)
N6—C32	1.473 (6)	C32—H32A	0.9700
N6—H6A	0.90 (5)	C32—H32B	0.9700
N7—C40	1.274 (5)	C33—H33A	0.9600
N7—C41	1.467 (5)	C33—H33B	0.9600
N8—C42	1.469 (6)	C33—H33C	0.9600
N8—C43	1.479 (6)	C34—C39	1.385 (6)
N8—H8	0.90 (3)	C34—C35	1.414 (5)
C1—C6	1.396 (6)	C34—C40	1.446 (6)
C1—C2	1.399 (5)	C35—C36	1.395 (5)
C1—C7	1.445 (6)	C36—C37	1.369 (6)
C2—C3	1.382 (6)	C36—H36	0.9300
C3—C4	1.377 (6)	C37—C38	1.378 (6)
C3—H3	0.9300	C37—H37	0.9300
C4—C5	1.380 (7)	C38—C39	1.379 (6)
C4—H4	0.9300	C38—H38	0.9300
C5—C6	1.351 (7)	C39—H39	0.9300
C5—H5	0.9300	C40—H40	0.9300
C6—H6	0.9300	C41—C42	1.496 (6)
C7—H7	0.9300	C41—H41A	0.9700
C8—C9	1.497 (6)	C41—H41B	0.9700
C8—H8A	0.9700	C42—H42A	0.9700
C8—H8B	0.9700	C42—H42B	0.9700
C9—H9A	0.9700	C43—C44	1.518 (6)
C9—H9B	0.9700	C43—H43A	0.9700
C10—C11	1.511 (6)	C43—H43B	0.9700
C10—H10A	0.9700	C44—H44A	0.9600
C10—H10B	0.9700	C44—H44B	0.9600
C11—H11A	0.9600	C44—H44C	0.9600
C11—H11B	0.9600

N3—Ni1—N1	176.64 (12)	H11A—C11—H11B	109.5
N3—Ni1—O2	84.89 (11)	C10—C11—H11C	109.5
N1—Ni1—O2	97.26 (11)	H11A—C11—H11C	109.5
N3—Ni1—O1	98.53 (12)	H11B—C11—H11C	109.5
N1—Ni1—O1	84.27 (12)	C17—C12—C13	118.8 (4)
O2—Ni1—O1	84.79 (10)	C17—C12—C18	117.0 (4)
N3—Ni1—N2	95.92 (14)	C13—C12—C18	124.1 (3)
N1—Ni1—N2	81.40 (14)	O2—C13—C14	120.2 (3)
O2—Ni1—N2	93.31 (12)	O2—C13—C12	121.8 (3)
O1—Ni1—N2	165.19 (12)	C14—C13—C12	118.1 (4)
N3—Ni1—N4	81.40 (13)	C15—C14—C13	121.6 (4)
N1—Ni1—N4	96.64 (13)	C15—C14—H14	119.2
O2—Ni1—N4	165.62 (12)	C13—C14—H14	119.2
O1—Ni1—N4	92.94 (13)	C16—C15—C14	120.4 (4)
N2—Ni1—N4	92.41 (14)	C16—C15—H15	119.8
N5—Ni2—N7	178.45 (12)	C14—C15—H15	119.8
N5—Ni2—O4	94.04 (12)	C17—C16—C15	119.2 (4)
N7—Ni2—O4	86.61 (12)	C17—C16—H16	120.4
N5—Ni2—O3	85.69 (12)	C15—C16—H16	120.4
N7—Ni2—O3	95.75 (12)	C16—C17—C12	121.9 (4)
O4—Ni2—O3	86.69 (10)	C16—C17—H17	119.1
N5—Ni2—N6	82.08 (14)	C12—C17—H17	119.1
N7—Ni2—N6	96.50 (14)	N3—C18—C12	125.9 (4)
O4—Ni2—N6	91.87 (12)	N3—C18—H18	117.0
O3—Ni2—N6	167.56 (12)	C12—C18—H18	117.0
N5—Ni2—N8	97.46 (14)	C20—C19—N3	110.4 (4)
N7—Ni2—N8	81.97 (14)	C20—C19—H19A	109.6
O4—Ni2—N8	167.99 (12)	N3—C19—H19A	109.6
O3—Ni2—N8	90.74 (12)	C20—C19—H19B	109.6
N6—Ni2—N8	93.11 (13)	N3—C19—H19B	109.6
O8—Cl1—O6	113.6 (4)	H19A—C19—H19B	108.1
O8—Cl1—O7	108.2 (4)	C19—C20—N4	110.2 (4)
O6—Cl1—O7	107.1 (3)	C19—C20—H20A	109.6
O8—Cl1—O5	107.8 (3)	N4—C20—H20A	109.6
O6—Cl1—O5	109.0 (3)	C19—C20—H20B	109.6
O7—Cl1—O5	111.2 (3)	N4—C20—H20B	109.6
O9'—Cl2—O12	67.8 (9)	H20A—C20—H20B	108.1
O9'—Cl2—O10	128.6 (11)	N4—C21—C22	115.0 (4)
O12—Cl2—O10	115.0 (6)	N4—C21—H21A	108.5
O9'—Cl2—O10'	113.4 (9)	C22—C21—H21A	108.5
O12—Cl2—O10'	130.0 (9)	N4—C21—H21B	108.5
O9'—Cl2—O11	115.6 (7)	C22—C21—H21B	108.5
O12—Cl2—O11	112.7 (4)	H21A—C21—H21B	107.5
O10—Cl2—O11	109.8 (5)	C21—C22—H22A	109.5
O10'—Cl2—O11	110.5 (9)	C21—C22—H22B	109.5
O12—Cl2—O9	105.8 (6)	H22A—C22—H22B	109.5
O10—Cl2—O9	106.8 (6)	C21—C22—H22C	109.5
O10'—Cl2—O9	84.8 (12)	H22A—C22—H22C	109.5
O11—Cl2—O9	106.1 (5)	H22B—C22—H22C	109.5
O9'—Cl2—O12'	107.5 (8)	C28—C23—C24	118.3 (4)
O10—Cl2—O12'	82.8 (9)	C28—C23—C29	117.3 (4)
O10'—Cl2—O12'	104.8 (8)	C24—C23—C29	124.4 (4)
O11—Cl2—O12'	103.9 (7)	O3—C24—C25	120.0 (4)
O9—Cl2—O12'	142.7 (7)	O3—C24—C23	121.5 (3)
C2—O1—Ni1	128.4 (2)	C25—C24—C23	118.5 (4)
C2—O1—H1	110 (3)	C26—C25—C24	121.6 (4)
Ni1—O1—H1	118 (3)	C26—C25—H25	119.2
C13—O2—Ni1	127.6 (2)	C24—C25—H25	119.2
C24—O3—Ni2	129.0 (2)	C27—C26—C25	120.1 (4)
C24—O3—H3A	112 (3)	C27—C26—H26	120.0
Ni2—O3—H3A	112 (3)	C25—C26—H26	120.0
C35—O4—Ni2	128.0 (2)	C28—C27—C26	119.6 (4)
C7—N1—C8	117.2 (4)	C28—C27—H27	120.2
C7—N1—Ni1	129.1 (3)	C26—C27—H27	120.2
C8—N1—Ni1	113.1 (3)	C27—C28—C23	121.9 (4)
C9—N2—C10	113.1 (4)	C27—C28—H28	119.1
C9—N2—Ni1	102.8 (2)	C23—C28—H28	119.1
C10—N2—Ni1	120.4 (3)	N5—C29—C23	126.1 (4)
C9—N2—H2	107 (3)	N5—C29—H29	116.9
C10—N2—H2	100 (3)	C23—C29—H29	116.9
Ni1—N2—H2	113 (3)	N5—C30—C31	110.6 (4)
C18—N3—C19	116.9 (3)	N5—C30—H30A	109.5
C18—N3—Ni1	129.4 (3)	C31—C30—H30A	109.5
C19—N3—Ni1	112.7 (2)	N5—C30—H30B	109.5
C21—N4—C20	111.6 (4)	C31—C30—H30B	109.5
C21—N4—Ni1	121.1 (3)	H30A—C30—H30B	108.1
C20—N4—Ni1	102.7 (3)	N6—C31—C30	110.8 (4)
C21—N4—H4A	112 (3)	N6—C31—H31A	109.5
C20—N4—H4A	103 (3)	C30—C31—H31A	109.5
Ni1—N4—H4A	104 (3)	N6—C31—H31B	109.5
C29—N5—C30	117.3 (4)	C30—C31—H31B	109.5
C29—N5—Ni2	130.5 (3)	H31A—C31—H31B	108.1
C30—N5—Ni2	112.2 (3)	N6—C32—C33	115.4 (4)
C31—N6—C32	110.4 (4)	N6—C32—H32A	108.4
C31—N6—Ni2	103.3 (3)	C33—C32—H32A	108.4
C32—N6—Ni2	118.6 (3)	N6—C32—H32B	108.4
C31—N6—H6A	100 (3)	C33—C32—H32B	108.4
C32—N6—H6A	115 (3)	H32A—C32—H32B	107.5
Ni2—N6—H6A	107 (3)	C32—C33—H33A	109.5
C40—N7—C41	118.4 (4)	C32—C33—H33B	109.5
C40—N7—Ni2	129.0 (3)	H33A—C33—H33B	109.5
C41—N7—Ni2	112.3 (3)	C32—C33—H33C	109.5
C42—N8—C43	113.3 (4)	H33A—C33—H33C	109.5
C42—N8—Ni2	103.5 (3)	H33B—C33—H33C	109.5
C43—N8—Ni2	118.5 (3)	C39—C34—C35	118.6 (4)
C42—N8—H8	107 (3)	C39—C34—C40	117.6 (4)
C43—N8—H8	106 (3)	C35—C34—C40	123.7 (4)
Ni2—N8—H8	108 (3)	O4—C35—C36	119.2 (4)
C6—C1—C2	117.7 (4)	O4—C35—C34	122.7 (4)
C6—C1—C7	118.5 (4)	C36—C35—C34	118.1 (4)
C2—C1—C7	123.8 (4)	C37—C36—C35	121.6 (4)
O1—C2—C3	120.1 (4)	C37—C36—H36	119.2
O1—C2—C1	120.8 (4)	C35—C36—H36	119.2
C3—C2—C1	119.1 (4)	C36—C37—C38	120.7 (4)
C4—C3—C2	121.6 (4)	C36—C37—H37	119.6
C4—C3—H3	119.2	C38—C37—H37	119.6
C2—C3—H3	119.2	C37—C38—C39	118.5 (4)
C3—C4—C5	119.5 (5)	C37—C38—H38	120.8
C3—C4—H4	120.3	C39—C38—H38	120.8
C5—C4—H4	120.3	C38—C39—C34	122.4 (4)
C6—C5—C4	119.3 (4)	C38—C39—H39	118.8
C6—C5—H5	120.3	C34—C39—H39	118.8
C4—C5—H5	120.3	N7—C40—C34	127.0 (4)
C5—C6—C1	122.8 (5)	N7—C40—H40	116.5
C5—C6—H6	118.6	C34—C40—H40	116.5
C1—C6—H6	118.6	N7—C41—C42	109.7 (4)
N1—C7—C1	128.0 (4)	N7—C41—H41A	109.7
N1—C7—H7	116.0	C42—C41—H41A	109.7
C1—C7—H7	116.0	N7—C41—H41B	109.7
N1—C8—C9	109.6 (3)	C42—C41—H41B	109.7
N1—C8—H8A	109.8	H41A—C41—H41B	108.2
C9—C8—H8A	109.8	N8—C42—C41	109.1 (4)
N1—C8—H8B	109.8	N8—C42—H42A	109.9
C9—C8—H8B	109.8	C41—C42—H42A	109.9
H8A—C8—H8B	108.2	N8—C42—H42B	109.9
N2—C9—C8	108.9 (4)	C41—C42—H42B	109.9
N2—C9—H9A	109.9	H42A—C42—H42B	108.3
C8—C9—H9A	109.9	N8—C43—C44	115.4 (4)
N2—C9—H9B	109.9	N8—C43—H43A	108.4
C8—C9—H9B	109.9	C44—C43—H43A	108.4
H9A—C9—H9B	108.3	N8—C43—H43B	108.4
N2—C10—C11	115.0 (4)	C44—C43—H43B	108.4
N2—C10—H10A	108.5	H43A—C43—H43B	107.5
C11—C10—H10A	108.5	C43—C44—H44A	109.5
N2—C10—H10B	108.5	C43—C44—H44B	109.5
C11—C10—H10B	108.5	H44A—C44—H44B	109.5
H10A—C10—H10B	107.5	C43—C44—H44C	109.5
C10—C11—H11A	109.5	H44A—C44—H44C	109.5
C10—C11—H11B	109.5	H44B—C44—H44C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.86 (3)	1.60 (3)	2.457 (4)	180 (6)
O3—H3A···O2	0.84 (4)	1.61 (5)	2.448 (3)	172 (5)
N4—H4A···O5	0.89 (4)	2.37 (4)	3.247 (6)	167 (4)
N6—H6A···O10ⁱ	0.90 (5)	2.52 (2)	3.411 (13)	174 (5)
N6—H6A···O10′ⁱ	0.90 (5)	2.27 (2)	3.16 (2)	174 (5)
N2—H2···Cl1	0.89 (4)	2.92 (4)	3.810 (4)	177 (4)
N2—H2···O8	0.89 (4)	2.52 (3)	3.316 (7)	149 (4)
N2—H2···O5	0.89 (4)	2.36 (2)	3.186 (6)	154 (5)
N8—H8···Cl2ⁱ	0.90 (3)	2.95 (3)	3.837 (4)	170 (4)
N8—H8···O10ⁱ	0.90 (3)	2.57 (3)	3.337 (10)	143 (4)
N8—H8···O11ⁱ	0.90 (3)	2.33 (2)	3.202 (5)	162 (5)
C8—H8B···O8	0.97	2.50	3.325 (7)	143
C18—H18···O6ⁱⁱ	0.93	2.60	3.500 (7)	163 (4)
C29—H29···O12ⁱⁱⁱ	0.93	2.54 (3)	3.410 (7)	155 (4)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y, z−1.

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