[2-(Imidazol-4-yl)ethylamine]{[2-(imidazol-4-yl)ethyl][(1-methylimidazol-2-yl)methyl]amine}copper(II) diperchlorate

In the title mononuclear complex, [Cu(C₅H₉N₃)(C₁₀H₁₅N₅)](ClO₄)₂, the Cu^II centre is surrounded by two N-donor ligands, which impose a square-pyramidal environment on the metal. The new tridentate ligand [2-(imidazol-4-yl)­ethyl]­[(1-methyl­imidazol-2-yl)­methyl]­amine (HISMIMA) lies in the basal plane, while the hist­amine ligand occupies the apical and one of the basal positions around the Cu^II ion.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai et al., 1996); software used to prepare material for publication: SHELXL97.

[(2-(Imidazol-4-yl)ethylamine]{[2-(imidazol-4-yl) ethyl][(1-methylimidazol-2-yl)methyl]amine}copper(II) diperchlorate

Crystal data

[Cu(C5H9N3)(C10H15N5)](ClO4)2	F(000) = 1188
Mr = 578.86	Dx = 1.635 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.785 (3) Å	Cell parameters from 25 reflections
b = 10.211 (2) Å	θ = 8.5–15.4°
c = 14.054 (3) Å	µ = 1.22 mm^−1
β = 102.54 (3)°	T = 293 K
V = 2351.3 (8) Å^3	Irregular, blue
Z = 4	0.43 × 0.26 × 0.23 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
ω/2θ scans	h = −19→19
Absorption correction: ψ-scan (PLATON; Spek, 1990)	k = 0→12
Tmin = 0.690, Tmax = 0.793	l = −16→0
4335 measured reflections	3 standard reflections every 200 reflections
4146 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.02	Calculated w = 1/[σ^2(Fo^2) + (0.0608P)^2] where P = (Fo^2 + 2Fc^2)/3
4146 reflections	(Δ/σ)max = 0.006
389 parameters	Δρmax = 0.35 e Å^−3
258 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. Notes - Abbreviations of the cited ligands:

B-MIMA: Bis[2-(1-methylimidazolyl)methyl]amine (Oberhausen et al., 1989);

2-MeIm₂PrO: 1,3-bis(N-methylimidazolimine)propan-2-ol (Doman et al., 1989);

bipa: Bis[2-(1-methylimidazolyl)methyl][2-(pyridyl)-methyl]amine and tmima: Tris[2-(1-methylimidazolyl)methyl]amine (Oberhausen et al., 1990);

L¹: Bis[(1-methylimidazol-2-yl)methyl][(1-methylimidazol-4-yl)methyl]amine and L²: Bis[(1-methylimidazol-4-yl)methyl][(1-methylimidazol-2-yl)methyl]amine (Chen et al., 1994);

hfac: hexafluoroacetylacetonato and L: [2-(imidazol-2-yl)ethyl][2-(methylimidazolyl)methyl]imine (Colacio, et al., 1998)

BIK: Bis(imidazol-2-yl)ketone (Place et al., 1998).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.24002 (3)	0.19364 (5)	0.10398 (3)	0.0465 (2)
N1	0.3154 (2)	0.2652 (4)	−0.0023 (2)	0.0576 (9)
H1A	0.2921	0.2351	−0.0621	0.069*
H1B	0.3127	0.3532	−0.0046	0.069*
N6	0.4157 (2)	0.0162 (4)	0.3115 (3)	0.0668 (11)
H6	0.4318	−0.0182	0.3683	0.080*
N8	0.33474 (18)	0.0950 (3)	0.1831 (2)	0.0481 (8)
N11	0.19253 (19)	0.0387 (3)	0.0275 (2)	0.0504 (9)
N13	0.1788 (2)	−0.1609 (4)	−0.0283 (3)	0.0652 (10)
H13	0.1891	−0.2420	−0.0370	0.078*
N18	0.13799 (19)	0.3065 (3)	0.0449 (3)	0.0605 (10)
H18	0.1491	0.3420	−0.0102	0.073*
N21	0.2633 (2)	0.3438 (3)	0.1948 (2)	0.0534 (9)
N24	0.2332 (3)	0.5438 (4)	0.2311 (3)	0.0627 (10)
C2	0.3993 (3)	0.2280 (7)	0.0189 (4)	0.105 (2)
H2A	0.4147	0.2172	−0.0450	0.126*	0.531 (12)
H2B	0.4301	0.2944	0.0526	0.126*	0.531 (12)
H2A'	0.4040	0.1471	−0.0157	0.126*	0.469 (12)
H2B'	0.4280	0.2946	−0.0097	0.126*	0.469 (12)
C3	0.4275 (3)	0.1117 (7)	0.0679 (4)	0.064 (3)	0.531 (12)
H3A	0.4857	0.1050	0.0713	0.077*	0.531 (12)
H3B	0.4016	0.0372	0.0309	0.077*	0.531 (12)
C3'	0.4422 (5)	0.2111 (12)	0.1134 (7)	0.070 (4)	0.469 (12)
H3'1	0.4399	0.2922	0.1487	0.084*	0.469 (12)
H3'2	0.4989	0.1954	0.1122	0.084*	0.469 (12)
C4	0.4135 (3)	0.1015 (6)	0.1709 (3)	0.0814 (16)
C5	0.4628 (3)	0.0528 (5)	0.2523 (4)	0.0775 (15)
H5	0.5194	0.0462	0.2643	0.093*
C7	0.3387 (3)	0.0418 (4)	0.2678 (3)	0.0563 (12)
H7	0.2938	0.0240	0.2945	0.068*
C12	0.2257 (3)	−0.0786 (4)	0.0338 (3)	0.0597 (12)
H12	0.2747	−0.1011	0.0755	0.072*
C14	0.1116 (3)	−0.0928 (5)	−0.0754 (3)	0.0635 (12)
H14	0.0683	−0.1256	−0.1222	0.076*
C15	0.1199 (3)	0.0298 (4)	−0.0415 (3)	0.0564 (12)
C16	0.0649 (3)	0.1441 (5)	−0.0698 (4)	0.0876 (17)
H16A	0.0103	0.1120	−0.0972	0.105*
H16B	0.0831	0.1924	−0.1205	0.105*
C17	0.0608 (3)	0.2357 (5)	0.0117 (4)	0.0801 (16)
H17A	0.0171	0.2982	−0.0099	0.096*
H17B	0.0484	0.1866	0.0657	0.096*
C19	0.1300 (3)	0.4182 (5)	0.1065 (4)	0.0786 (15)
H19A	0.0868	0.4021	0.1410	0.094*
H19B	0.1160	0.4959	0.0666	0.094*
C20	0.2086 (3)	0.4387 (5)	0.1773 (3)	0.0558 (11)
C22	0.3268 (3)	0.3919 (5)	0.2640 (3)	0.0644 (13)
H22	0.3746	0.3471	0.2909	0.077*
C23	0.3086 (3)	0.5149 (5)	0.2864 (4)	0.0745 (14)
H23	0.3414	0.5700	0.3313	0.089*
C25	0.1923 (4)	0.6710 (5)	0.2237 (4)	0.0918 (18)
H25A	0.2162	0.7236	0.2791	0.138*
H25B	0.1354	0.6584	0.2219	0.138*
H25C	0.1986	0.7143	0.1651	0.138*
Cl1	0.10205 (7)	1.00686 (13)	0.30554 (10)	0.0673 (4)
O1	0.1132 (12)	0.9288 (19)	0.2316 (14)	0.220 (17)	0.40 (2)
O1'	0.1203 (7)	0.9659 (13)	0.2187 (6)	0.137 (5)	0.60 (2)
O2	0.0251 (7)	1.0511 (19)	0.2978 (16)	0.122 (8)	0.40 (2)
O2'	0.0323 (6)	1.0851 (12)	0.2823 (9)	0.135 (6)	0.60 (2)
O3	0.1590 (11)	1.1047 (14)	0.325 (2)	0.190 (13)	0.40 (2)
O3'	0.1671 (4)	1.0848 (11)	0.3556 (7)	0.097 (5)	0.60 (2)
O4	0.1162 (16)	0.923 (2)	0.3876 (14)	0.240 (18)	0.40 (2)
O4'	0.0913 (8)	0.9065 (12)	0.3641 (11)	0.167 (7)	0.60 (2)
Cl2	0.36708 (7)	−0.15885 (11)	0.52239 (9)	0.0608 (3)
O5	0.2913 (6)	−0.1158 (12)	0.5396 (13)	0.126 (4)	0.67 (3)
O5'	0.2913 (7)	−0.0964 (17)	0.496 (2)	0.110 (7)	0.33 (3)
O6	0.3539 (9)	−0.2112 (17)	0.4312 (7)	0.124 (4)	0.67 (3)
O6'	0.3663 (11)	−0.262 (2)	0.4547 (17)	0.115 (8)	0.33 (3)
O7	0.3999 (10)	−0.2480 (13)	0.5925 (12)	0.180 (6)	0.67 (3)
O7'	0.3748 (16)	−0.216 (3)	0.6139 (9)	0.127 (9)	0.33 (3)
O8	0.4169 (7)	−0.0422 (11)	0.5250 (10)	0.068 (3)	0.67 (3)
O8'	0.4351 (10)	−0.082 (2)	0.5159 (17)	0.051 (5)	0.33 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0385 (3)	0.0515 (3)	0.0470 (3)	0.0041 (2)	0.0036 (2)	0.0011 (3)
N1	0.057 (2)	0.063 (2)	0.051 (2)	−0.0037 (19)	0.0105 (17)	0.0072 (19)
N6	0.070 (3)	0.088 (3)	0.039 (2)	0.024 (2)	0.005 (2)	0.015 (2)
N8	0.0404 (19)	0.058 (2)	0.044 (2)	0.0043 (16)	0.0036 (15)	0.0069 (18)
N11	0.044 (2)	0.049 (2)	0.054 (2)	−0.0012 (17)	0.0015 (17)	0.0020 (17)
N13	0.073 (3)	0.052 (2)	0.072 (3)	−0.005 (2)	0.021 (2)	−0.007 (2)
N18	0.046 (2)	0.064 (2)	0.066 (2)	0.0134 (18)	0.0003 (18)	−0.007 (2)
N21	0.058 (2)	0.053 (2)	0.047 (2)	0.0009 (19)	0.0066 (18)	−0.0004 (17)
N24	0.090 (3)	0.054 (2)	0.051 (2)	0.003 (2)	0.029 (2)	−0.003 (2)
C2	0.064 (4)	0.170 (6)	0.091 (4)	0.018 (4)	0.035 (3)	0.056 (4)
C3	0.058 (6)	0.069 (7)	0.072 (7)	0.005 (5)	0.029 (5)	−0.001 (6)
C3'	0.039 (5)	0.105 (11)	0.063 (8)	−0.009 (6)	0.007 (5)	0.013 (7)
C4	0.048 (3)	0.128 (5)	0.070 (3)	0.013 (3)	0.017 (3)	0.044 (3)
C5	0.045 (3)	0.106 (4)	0.076 (4)	0.013 (3)	0.002 (3)	0.022 (3)
C7	0.054 (3)	0.061 (3)	0.055 (3)	0.011 (2)	0.014 (2)	0.013 (2)
C12	0.057 (3)	0.056 (3)	0.064 (3)	0.001 (3)	0.008 (2)	−0.001 (3)
C14	0.051 (3)	0.068 (3)	0.068 (3)	−0.010 (3)	0.005 (2)	−0.004 (3)
C15	0.049 (3)	0.054 (3)	0.061 (3)	−0.006 (2)	0.001 (2)	−0.001 (2)
C16	0.061 (3)	0.078 (4)	0.101 (4)	0.000 (3)	−0.031 (3)	−0.003 (3)
C17	0.039 (3)	0.080 (4)	0.113 (4)	0.009 (3)	−0.002 (3)	−0.005 (3)
C19	0.074 (3)	0.084 (4)	0.075 (3)	0.025 (3)	0.010 (3)	−0.014 (3)
C20	0.066 (3)	0.060 (3)	0.044 (3)	0.003 (3)	0.017 (2)	−0.002 (2)
C22	0.074 (3)	0.065 (3)	0.048 (3)	−0.001 (3)	0.001 (2)	−0.009 (2)
C23	0.086 (4)	0.077 (4)	0.059 (3)	−0.018 (3)	0.012 (3)	−0.014 (3)
C25	0.145 (5)	0.063 (4)	0.078 (4)	0.019 (3)	0.046 (4)	−0.006 (3)
Cl1	0.0565 (8)	0.0676 (9)	0.0719 (9)	0.0094 (7)	0.0008 (6)	−0.0098 (7)
O1	0.18 (2)	0.152 (16)	0.31 (3)	0.082 (14)	0.003 (18)	−0.16 (2)
O1'	0.119 (9)	0.245 (14)	0.054 (6)	−0.044 (9)	0.032 (5)	−0.055 (6)
O2	0.034 (7)	0.090 (11)	0.26 (2)	0.005 (6)	0.068 (10)	0.002 (11)
O2'	0.103 (9)	0.087 (7)	0.174 (10)	0.033 (6)	−0.060 (8)	−0.019 (6)
O3	0.18 (2)	0.072 (10)	0.36 (3)	−0.060 (11)	0.14 (2)	−0.025 (14)
O3'	0.033 (4)	0.163 (12)	0.086 (6)	0.001 (5)	−0.007 (4)	−0.073 (6)
O4	0.33 (3)	0.20 (3)	0.159 (18)	0.14 (3)	−0.026 (19)	0.082 (17)
O4'	0.137 (8)	0.162 (13)	0.215 (16)	−0.009 (9)	0.065 (8)	0.100 (12)
Cl2	0.0596 (8)	0.0633 (8)	0.0572 (8)	−0.0139 (6)	0.0076 (6)	0.0006 (6)
O5	0.141 (9)	0.101 (7)	0.174 (10)	−0.025 (6)	0.117 (8)	−0.042 (7)
O5'	0.029 (7)	0.124 (12)	0.175 (17)	0.008 (7)	0.019 (8)	0.064 (13)
O6	0.204 (10)	0.085 (7)	0.094 (6)	−0.058 (6)	0.057 (6)	−0.047 (5)
O6'	0.126 (12)	0.074 (12)	0.18 (2)	−0.040 (9)	0.110 (14)	−0.080 (11)
O7	0.155 (9)	0.134 (8)	0.208 (14)	−0.055 (7)	−0.056 (9)	0.109 (10)
O7'	0.169 (19)	0.166 (18)	0.038 (9)	−0.102 (14)	0.005 (10)	0.006 (10)
O8	0.065 (5)	0.051 (5)	0.081 (5)	−0.011 (4)	0.003 (4)	−0.003 (4)
O8'	0.041 (7)	0.046 (9)	0.063 (8)	−0.003 (6)	0.006 (5)	0.013 (7)

Geometric parameters (Å, º)

Cu1—N21	1.980 (3)	C4—C5	1.353 (6)
Cu1—N11	1.980 (3)	C14—C15	1.337 (6)
Cu1—N8	2.003 (3)	C15—C16	1.487 (6)
Cu1—N18	2.082 (3)	C16—C17	1.492 (7)
Cu1—N1	2.277 (3)	C19—C20	1.485 (6)
N1—C2	1.427 (5)	C22—C23	1.346 (7)
N6—C5	1.321 (6)	Cl1—O2	1.350 (10)
N6—C7	1.330 (5)	Cl1—O4'	1.351 (8)
N8—C7	1.297 (5)	Cl1—O1	1.354 (11)
N8—C4	1.371 (5)	Cl1—O3	1.368 (11)
N11—C12	1.316 (5)	Cl1—O1'	1.385 (7)
N11—C15	1.386 (5)	Cl1—O2'	1.396 (9)
N13—C12	1.337 (5)	Cl1—O3'	1.409 (6)
N13—C14	1.368 (5)	Cl1—O4	1.412 (12)
N18—C19	1.455 (5)	Cl2—O6	1.361 (7)
N18—C17	1.468 (5)	Cl2—O7	1.366 (8)
N21—C20	1.321 (5)	Cl2—O7'	1.392 (12)
N21—C22	1.368 (5)	Cl2—O5'	1.399 (10)
N24—C20	1.326 (5)	Cl2—O8'	1.404 (12)
N24—C23	1.366 (6)	Cl2—O5	1.415 (8)
N24—C25	1.461 (6)	Cl2—O6'	1.418 (12)
C2—C3'	1.377 (8)	Cl2—O8	1.451 (8)
C2—C3	1.4021	O5—O5'	0.64 (2)
C3—C3'	1.196 (13)	O6—O6'	0.63 (2)
C3—C4	1.520 (6)	O7—O7'	0.66 (2)
C3'—C4	1.518 (9)	O8—O8'	0.541 (18)
N21—Cu1—N11	165.65 (14)	O2—Cl1—O3	112.7 (9)
N21—Cu1—N8	90.59 (14)	O4'—Cl1—O3	127.6 (12)
N11—Cu1—N8	94.41 (14)	O1—Cl1—O3	112.2 (9)
N21—Cu1—N18	81.85 (14)	O2—Cl1—O1'	114.9 (12)
N11—Cu1—N18	91.51 (14)	O4'—Cl1—O1'	113.1 (7)
N8—Cu1—N18	170.11 (14)	O1—Cl1—O1'	18.7 (10)
N21—Cu1—N1	96.60 (14)	O3—Cl1—O1'	96.9 (11)
N11—Cu1—N1	96.64 (14)	O2—Cl1—O2'	18.4 (10)
N8—Cu1—N1	92.21 (13)	O4'—Cl1—O2'	111.1 (7)
N18—Cu1—N1	94.97 (14)	O1—Cl1—O2'	114.0 (11)
C2—N1—Cu1	116.2 (3)	O3—Cl1—O2'	98.2 (11)
C5—N6—C7	108.0 (4)	O1'—Cl1—O2'	107.5 (6)
C7—N8—C4	106.0 (3)	O2—Cl1—O3'	118.3 (9)
C7—N8—Cu1	126.6 (3)	O4'—Cl1—O3'	108.4 (6)
C4—N8—Cu1	125.2 (3)	O1—Cl1—O3'	119.6 (10)
C12—N11—C15	106.4 (4)	O3—Cl1—O3'	19.2 (11)
C12—N11—Cu1	125.2 (3)	O1'—Cl1—O3'	108.4 (5)
C15—N11—Cu1	128.4 (3)	O2'—Cl1—O3'	108.2 (6)
C12—N13—C14	107.7 (4)	O2—Cl1—O4	104.8 (9)
C19—N18—C17	112.7 (4)	O4'—Cl1—O4	20.8 (11)
C19—N18—Cu1	111.8 (3)	O1—Cl1—O4	104.2 (9)
C17—N18—Cu1	116.5 (3)	O3—Cl1—O4	106.8 (7)
C20—N21—C22	105.8 (4)	O1'—Cl1—O4	120.5 (11)
C20—N21—Cu1	114.6 (3)	O2'—Cl1—O4	121.3 (11)
C22—N21—Cu1	138.6 (3)	O3'—Cl1—O4	87.6 (11)
C20—N24—C23	106.6 (4)	O6—Cl2—O7	112.0 (6)
C20—N24—C25	126.5 (4)	O6—Cl2—O7'	132.0 (10)
C23—N24—C25	126.5 (5)	O7—Cl2—O7'	27.5 (9)
C3'—C2—C3	51.0 (5)	O6—Cl2—O5'	88.8 (11)
C3'—C2—N1	121.3 (5)	O7—Cl2—O5'	133.9 (9)
C3—C2—N1	122.7 (3)	O7'—Cl2—O5'	109.3 (7)
C3'—C3—C2	63.4 (4)	O6—Cl2—O8'	97.3 (12)
C3'—C3—C4	66.8 (4)	O7—Cl2—O8'	102.3 (11)
C2—C3—C4	114.9 (3)	O7'—Cl2—O8'	112.3 (10)
C3—C3'—C2	65.6 (5)	O5'—Cl2—O8'	115.8 (9)
C3—C3'—C4	66.9 (6)	O6—Cl2—O5	108.3 (6)
C2—C3'—C4	116.5 (7)	O7—Cl2—O5	108.7 (6)
C5—C4—N8	107.8 (4)	O7'—Cl2—O5	83.1 (9)
C5—C4—C3'	121.0 (5)	O5'—Cl2—O5	26.3 (8)
N8—C4—C3'	121.8 (5)	O8'—Cl2—O5	127.7 (8)
C5—C4—C3	129.6 (5)	O6—Cl2—O6'	25.9 (9)
N8—C4—C3	118.4 (4)	O7—Cl2—O6'	86.1 (10)
C3'—C4—C3	46.4 (5)	O7'—Cl2—O6'	107.1 (8)
N6—C5—C4	107.2 (4)	O5'—Cl2—O6'	106.7 (9)
N8—C7—N6	110.9 (4)	O8'—Cl2—O6'	105.1 (8)
N11—C12—N13	110.4 (4)	O5—Cl2—O6'	117.9 (9)
C15—C14—N13	107.0 (4)	O6—Cl2—O8	108.7 (6)
C14—C15—N11	108.6 (4)	O7—Cl2—O8	112.9 (6)
C14—C15—C16	129.0 (4)	O7'—Cl2—O8	112.5 (12)
N11—C15—C16	122.4 (4)	O5'—Cl2—O8	96.8 (9)
C15—C16—C17	114.6 (4)	O8'—Cl2—O8	21.8 (7)
N18—C17—C16	111.6 (4)	O5—Cl2—O8	106.0 (5)
N18—C19—C20	109.1 (4)	O6'—Cl2—O8	123.3 (9)
N21—C20—N24	111.7 (4)	O5'—O5—Cl2	75.5 (14)
N21—C20—C19	120.1 (4)	O5—O5'—Cl2	78.2 (14)
N24—C20—C19	128.2 (4)	O6'—O6—Cl2	82.1 (16)
C23—C22—N21	108.7 (4)	O6—O6'—Cl2	71.9 (15)
C22—C23—N24	107.3 (4)	O7'—O7—Cl2	78.5 (16)
O2—Cl1—O4'	92.9 (10)	O7—O7'—Cl2	74.0 (14)
O2—Cl1—O1	115.2 (10)	O8'—O8—Cl2	74.2 (19)
O4'—Cl1—O1	94.6 (12)	O8—O8'—Cl2	84.0 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5^i	0.90	2.79	3.665 (15)	164
N1—H1B···O5′^i	0.90	2.51	3.405 (19)	174
N6—H6···O8	0.86	2.28	3.055 (14)	149
N6—H6···O8′	0.86	2.16	2.99 (2)	162
N13—H13···O5^ii	0.86	2.33	2.982 (11)	133
N13—H13···O5′^ii	0.86	2.35	3.089 (18)	144
N13—H13···O4^i	0.86	2.34	3.025 (16)	136
N13—H13···O4′^i	0.86	2.54	3.126 (12)	126
N18—H18···O3^iii	0.91	2.42	3.31 (3)	167
N18—H18···O3′^iii	0.91	2.11	3.018 (9)	175

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y−1/2, z−1/2; (iii) x, −y+3/2, z−1/2.