Bis{2-[2,5-bis­(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium} tetra­cyanidoplatinate(II) tetra­hydrate

The asymmetric unit of the title hydrated complex salt, (C₁₈H₁₄N₅)₂[Pt(CN)₄]·4H₂O, consists of one 2-[2,5-bis­(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium cation, half a tetra­cyanidoplatinate(II) dianion, which is located about a crystallographic inversion center, and two water mol­ecules of crystallization. The Pt^II atom has a square-planar coordination environment, with Pt—C_CN distances of 1.992 (4) and 2.000 (4) Å. In the cation, there is an N—H...N hydrogen bond linking adjacent pyridinium and pyridine rings in positions 4 and 5. Despite this, the organic component is non-planar, as shown by the dihedral angles of 10.3 (2), 6.60 (19) and 15.66 (18)° between the planes of the central imidazole ring and the pyridine/pyridinium substituents in the 2-, 4- and 5-positions. In the crystal, cations and anions are linked via O—H...O, O—H...N and N—H...O hydrogen bonds, forming a three-dimensional network. Additional π–π, C—H...O and C—H...N contacts provide stabilization to the crystal lattice.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.032
• wR factor = 0.078
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1'    ..  H31A    ..       2.03 Ang.

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O32     ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17    ..  O32     ..       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  O32     ..       2.70 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          2

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          8
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          64 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Hydrogen bond based inorganic–organic hybrid materials are receiving continuous interest because of their structural, magnetic, optical and electrical properties (Sanchez et al., 2005; Yao et al., 2010; Wang et al., 2010; Lebeau et al., 2011; Pardo et al., 2011; Du et al., 2013). An interesting approach for the preparation of such materials consists in the utilization of supramolecular synthons capable of forming O—H···O, O—H···N and N—H···O hydrogen bonds, through which organic cations and anionic metal complexes are linked to form crystalline inorganic–organic hybrid solids (Crawford et al., 2004; Dechambenoit et al., 2006; Maynard & Sykora, 2008). As a further contribution to this filed of research we report herein on the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound consists of one organic cation of the composition [(C₁₈H₁₄N₅)]⁺, which is located in a general position, half of an independent [Pt(CN)₄]^2- anion, which is located on a crystallographic inversion center, and two water molecules of crystallization (Fig. 1). The Pt atom has a square-planar coordination environment with Pt—C(cyanido) distances ranging from 1.992 (4) to 2.000 (4) Å. Although two of the three pyridine substituents are linked by an intramolecular N5⁺—H5'···N4 hydrogen bond (Table 1), the organic component is essentially nonplanar, as shown by the dihedral angles of 10.3 (2), 6.60 (19) and 15.66 (18)°, respectively, formed between the central imidazole ring plane and the pyridine substituents in the 2-, 4- and 5-positions.

In the crystal, the cations and anions are linked by O—H···O, O—H···N and N—H···O hydrogen bonds forming a three-dimensional network (Table 1 and Fig. 2). Within the network, the organic cations are stacked through a series of π—π interactions involving the imidazole and pyridinium rings [Cg1···Cg1ⁱ distance = 3.359 (2) Å; Cg1···Cg2ⁱⁱ distance = 3.559 (2) Å; Cg3···Cg3ⁱⁱⁱ distance = 4.023 (3) Å; Cg2···Cg3ⁱ distance = 3.929 (2) Å; Cg1= N1/C1/N2/C3/C2; Cg2 = N4/C9-C13 and Cg3 = N3/C4—C8; symmetry codes: (i) –x+1, -y+1, -z; (ii) –x+1, y, 1- z+1/2; (iii)-x+1/2, - y+3/2, -z]. Additionally, there are a number of C—H···O and C—H···N contacts present, thus providing additional stabilization to the crystal lattice (Table 1 and Fig. 2).

Related literature

For the structural, magnetic, optical and electrical properties of hydrogen-bonded inorganic–organic hybrid materials, see: Anastassiadou et al. (2000); Crawford et al. (2004); Dechambenoit et al. (2006); Du et al. (2013); Lebeau & Innocenzi (2011); Maynard & Sykora (2008); Pardo et al. (2011); Sanchez et al. (2005); Wang et al. (2010); Yao et al. (2010).

S2. Experimental

The organic component in the title compound, 2-(2,5-di(pyridin-2-yl)-1H-imidazol-4-yl)pyridine, was synthesized according to a previously reported procedure (Anastassiadou et al., 2000). Single crystals of the platinum complex were prepared at room temperature by slow diffusion of a CH₃CN/H₂O (2 ml, 1:1 v/v) solution containing both Eu(NO₃)₃ ^. 6H₂O (0.034 g, 0.08 mmol) and K₂Pt(CN)₄ (0.030 g, 0.08 mmol) into a CH₂Cl₂ (2 ml) solution of 2-(2,5-di(pyridin-2-yl)-1H-imidazol-4-yl)pyridine (0.024 g, 0.08 mmol). After two weeks, pale yellow crystals were obtained [Yield: 40%]. IR and TGA details are given in the archived CIF.

S3. Refinement

The C-bound H atoms were positioned geometrically and refined as riding atoms [aryl C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C)]. The pyridinium N—H⁺ and water H atoms were located in difference Fourier maps. They were refined with distance restraints of 0.840 (1)Å, with U_iso(H) = 1.5U_eq(O, N). For the refinement of the water molecules a constraint has also been employed for the H—O—H bond angles (DANG = 1.35 (1) Å). In the final difference Fourier map a large residual density peak, 3.10 eÅ^-3, and hole, -2.26 eÅ^-3, were found near the Pt atom.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker 2001); data reduction: SAINT-Plus (Bruker 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (i) -x + 1/2, -y + 3/2, -z + 1].
	Fig. 2. A view along the b axis of the crystal packing of the title compound, showing the O—H···O, O—H···N, N—H···O, C—H···O and C—H···N hydrogen bonded three-dimensional supramolecular network (hydrogen bonds are shown as dashed lines; see Table 1 for details).

Bis{2-[2,5-bis(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium} tetracyanidoplatinate(II) tetrahydrate

Crystal data

(C18H14N5)2[Pt(CN)4]·4H2O	F(000) = 1936
Mr = 971.92	Dx = 1.667 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9440 reflections
a = 20.958 (5) Å	θ = 2.3–27.7°
b = 12.048 (3) Å	µ = 3.69 mm^−1
c = 15.403 (3) Å	T = 100 K
β = 95.483 (3)°	Rectangular prism, yellow
V = 3871.6 (14) Å^3	0.50 × 0.34 × 0.28 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	3418 independent reflections
Radiation source: fine-focus sealed tube	2726 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.26, Tmax = 0.43	k = −14→14
17095 measured reflections	l = −18→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0497P)^2] where P = (Fo^2 + 2Fc^2)/3
3418 reflections	(Δ/σ)max < 0.001
286 parameters	Δρmax = 3.10 e Å^−3
8 restraints	Δρmin = −2.27 e Å^−3

Special details

Experimental. IR and TGA details for the title compound: IR(KBr, cm^-1): 3406, 3385, 3268, 3100, 2129, 1661, 1596, 1501, 1447, 1235, 1139, 1096, 777, 703. TGA: Calcd. for 4H₂O: 7.42. Found: 7.69% (298 - 385 K).

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 (Ų)

	x	y	z	Uiso*/Ueq
Pt1	0.2500	0.7500	0.5000	0.01672 (10)
N1	0.96962 (15)	1.0885 (2)	0.10252 (19)	0.0173 (7)
H1'	0.973 (2)	1.1564 (9)	0.114 (3)	0.026*
N2	0.92075 (14)	0.9356 (2)	0.05054 (18)	0.0179 (7)
N3	0.87601 (18)	1.2211 (3)	−0.0001 (2)	0.0226 (8)
N4	1.09913 (14)	0.9336 (2)	0.22311 (18)	0.0171 (7)
N5	1.03998 (19)	0.7543 (2)	0.1645 (2)	0.0189 (8)
H5'	1.0631 (17)	0.798 (3)	0.196 (2)	0.028*
N6	0.31880 (15)	0.8613 (3)	0.6676 (2)	0.0256 (8)
N7	0.32877 (17)	0.9085 (3)	0.3882 (2)	0.0320 (8)
C1	0.91839 (17)	1.0457 (3)	0.0535 (2)	0.0181 (8)
C2	1.00799 (17)	1.0022 (3)	0.1331 (2)	0.0168 (8)
C3	0.97619 (18)	0.9069 (3)	0.1007 (2)	0.0170 (9)
C4	0.86797 (17)	1.1094 (3)	0.0042 (2)	0.0188 (8)
C5	0.81594 (17)	1.0555 (3)	−0.0383 (2)	0.0238 (9)
H5	0.8109	0.9777	−0.0321	0.029*
C6	0.77141 (19)	1.1165 (3)	−0.0900 (2)	0.0286 (10)
H6	0.7355	1.0812	−0.1206	0.034*
C7	0.7798 (3)	1.2285 (4)	−0.0962 (3)	0.0325 (11)
H7	0.7502	1.2718	−0.1325	0.039*
C8	0.8316 (2)	1.2785 (4)	−0.0496 (3)	0.0290 (10)
H8	0.8358	1.3568	−0.0528	0.035*
C9	1.07022 (17)	1.0222 (3)	0.1828 (2)	0.0172 (8)
C10	1.09906 (18)	1.1263 (3)	0.1866 (2)	0.0201 (8)
H10	1.0780	1.1884	0.1588	0.024*
C11	1.15875 (19)	1.1376 (3)	0.2316 (2)	0.0218 (9)
H11	1.1794	1.2079	0.2344	0.026*
C12	1.18881 (19)	1.0470 (3)	0.2727 (2)	0.0225 (9)
H12	1.2301	1.0535	0.3037	0.027*
C13	1.15672 (18)	0.9468 (3)	0.2671 (2)	0.0218 (9)
H13	1.1765	0.8842	0.2959	0.026*
C14	0.99006 (18)	0.7888 (3)	0.1090 (2)	0.0155 (8)
C15	0.95298 (19)	0.7094 (3)	0.0622 (2)	0.0196 (9)
H15	0.9177	0.7314	0.0226	0.023*
C16	0.9678 (2)	0.5986 (3)	0.0734 (3)	0.0241 (9)
H16	0.9424	0.5439	0.0420	0.029*
C17	1.01988 (19)	0.5669 (3)	0.1306 (2)	0.0230 (9)
H17	1.0306	0.4907	0.1386	0.028*
C18	1.05545 (19)	0.6473 (3)	0.1752 (2)	0.0215 (9)
H18	1.0914	0.6269	0.2141	0.026*
C19	0.29365 (18)	0.8199 (3)	0.6075 (2)	0.0204 (9)
C20	0.29937 (19)	0.8513 (3)	0.4291 (2)	0.0220 (9)
O31	0.96490 (15)	0.3159 (2)	0.1280 (2)	0.0341 (7)
H31A	0.9379 (13)	0.310 (4)	0.0842 (14)	0.051*
H32A	0.1394 (19)	0.481 (2)	0.304 (2)	0.051*
O32	0.12373 (15)	0.4241 (2)	0.27892 (18)	0.0324 (7)
H31B	0.9448 (15)	0.334 (4)	0.1704 (15)	0.049*
H32B	0.135 (2)	0.426 (3)	0.2280 (11)	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01960 (15)	0.01288 (15)	0.01807 (14)	0.00058 (8)	0.00385 (8)	−0.00070 (7)
N1	0.0203 (18)	0.0123 (16)	0.0202 (16)	0.0003 (15)	0.0066 (13)	−0.0003 (14)
N2	0.0202 (18)	0.0155 (17)	0.0191 (16)	−0.0003 (14)	0.0083 (13)	0.0013 (13)
N3	0.027 (2)	0.0138 (16)	0.029 (2)	0.0015 (16)	0.0114 (15)	0.0038 (15)
N4	0.0224 (18)	0.0111 (16)	0.0184 (16)	0.0006 (14)	0.0048 (13)	0.0000 (13)
N5	0.021 (2)	0.016 (2)	0.0201 (19)	−0.0058 (14)	0.0047 (14)	−0.0014 (13)
N6	0.026 (2)	0.0281 (19)	0.0228 (18)	−0.0027 (16)	0.0053 (15)	−0.0046 (15)
N7	0.035 (2)	0.031 (2)	0.031 (2)	−0.0065 (17)	0.0077 (16)	0.0025 (16)
C1	0.019 (2)	0.018 (2)	0.0183 (19)	0.0004 (17)	0.0099 (16)	0.0001 (16)
C2	0.022 (2)	0.013 (2)	0.0169 (19)	0.0014 (17)	0.0098 (15)	0.0005 (16)
C3	0.020 (2)	0.018 (2)	0.0152 (19)	−0.0019 (17)	0.0090 (16)	0.0016 (16)
C4	0.020 (2)	0.018 (2)	0.0200 (19)	0.0058 (17)	0.0117 (16)	0.0013 (16)
C5	0.023 (2)	0.024 (2)	0.025 (2)	−0.0002 (19)	0.0073 (17)	−0.0027 (17)
C6	0.026 (2)	0.030 (2)	0.030 (2)	0.006 (2)	0.0015 (17)	−0.0021 (19)
C7	0.033 (3)	0.034 (3)	0.030 (3)	0.011 (2)	0.002 (2)	0.006 (2)
C8	0.035 (3)	0.021 (2)	0.033 (3)	0.005 (2)	0.014 (2)	0.008 (2)
C9	0.022 (2)	0.016 (2)	0.0156 (19)	0.0004 (17)	0.0100 (15)	−0.0019 (15)
C10	0.028 (2)	0.0115 (19)	0.022 (2)	0.0001 (18)	0.0067 (16)	0.0003 (16)
C11	0.025 (2)	0.015 (2)	0.026 (2)	−0.0034 (18)	0.0045 (17)	−0.0038 (17)
C12	0.026 (2)	0.019 (2)	0.022 (2)	−0.0032 (18)	0.0025 (17)	−0.0033 (17)
C13	0.028 (2)	0.017 (2)	0.021 (2)	0.0022 (18)	0.0054 (17)	0.0052 (16)
C14	0.018 (2)	0.0142 (17)	0.016 (2)	−0.0009 (18)	0.0092 (16)	0.0017 (16)
C15	0.021 (2)	0.0181 (19)	0.020 (2)	0.0000 (19)	0.0057 (16)	0.0009 (17)
C16	0.029 (2)	0.019 (2)	0.025 (2)	−0.0070 (19)	0.0061 (18)	−0.0042 (17)
C17	0.028 (2)	0.012 (2)	0.030 (2)	−0.0029 (19)	0.0095 (18)	0.0008 (17)
C18	0.025 (2)	0.018 (2)	0.023 (2)	−0.0006 (18)	0.0058 (16)	0.0064 (17)
C19	0.024 (2)	0.019 (2)	0.020 (2)	0.0026 (18)	0.0069 (17)	0.0014 (17)
C20	0.025 (2)	0.019 (2)	0.022 (2)	−0.0011 (18)	0.0024 (17)	−0.0068 (17)
O31	0.0371 (19)	0.0219 (17)	0.0444 (19)	−0.0019 (15)	0.0096 (14)	−0.0049 (15)
O32	0.046 (2)	0.0254 (16)	0.0277 (16)	−0.0057 (15)	0.0115 (14)	−0.0006 (13)

Geometric parameters (Å, º)

Pt1—C20	1.992 (4)	C6—C7	1.365 (5)
Pt1—C20^i	1.992 (4)	C6—H6	0.9500
Pt1—C19	2.000 (4)	C7—C8	1.381 (7)
Pt1—C19^i	2.000 (4)	C7—H7	0.9500
N1—C1	1.354 (5)	C8—H8	0.9500
N1—C2	1.370 (5)	C9—C10	1.391 (5)
N1—H1'	0.8400 (11)	C10—C11	1.378 (5)
N2—C1	1.328 (4)	C10—H10	0.9500
N2—C3	1.377 (5)	C11—C12	1.383 (5)
N3—C8	1.338 (6)	C11—H11	0.9500
N3—C4	1.358 (5)	C12—C13	1.381 (5)
N4—C13	1.336 (5)	C12—H12	0.9500
N4—C9	1.349 (4)	C13—H13	0.9500
N5—C18	1.336 (4)	C14—C15	1.391 (6)
N5—C14	1.351 (6)	C15—C16	1.377 (6)
N5—H5'	0.8400 (11)	C15—H15	0.9500
N6—C19	1.135 (5)	C16—C17	1.390 (6)
N7—C20	1.151 (4)	C16—H16	0.9500
C1—C4	1.459 (5)	C17—C18	1.367 (5)
C2—C3	1.396 (5)	C17—H17	0.9500
C2—C9	1.467 (5)	C18—H18	0.9500
C3—C14	1.455 (5)	O31—H31A	0.8401 (11)
C4—C5	1.380 (5)	O31—H31B	0.8400 (11)
C5—C6	1.379 (5)	O32—H32A	0.8401 (11)
C5—H5	0.9500	O32—H32B	0.8400 (11)
C20—Pt1—C20^i	180.00 (17)	N3—C8—H8	118.6
C20—Pt1—C19	88.59 (15)	C7—C8—H8	118.6
C20^i—Pt1—C19	91.41 (14)	N4—C9—C10	121.3 (3)
C20—Pt1—C19^i	91.41 (14)	N4—C9—C2	116.6 (3)
C20^i—Pt1—C19^i	88.59 (15)	C10—C9—C2	122.1 (3)
C19—Pt1—C19^i	180.000 (1)	C11—C10—C9	118.7 (3)
C1—N1—C2	108.2 (3)	C11—C10—H10	120.6
C1—N1—H1'	123 (3)	C9—C10—H10	120.6
C2—N1—H1'	129 (3)	C10—C11—C12	120.3 (4)
C1—N2—C3	105.3 (3)	C10—C11—H11	119.8
C8—N3—C4	117.2 (4)	C12—C11—H11	119.8
C13—N4—C9	118.9 (3)	C13—C12—C11	117.6 (4)
C18—N5—C14	122.6 (4)	C13—C12—H12	121.2
C18—N5—H5'	115 (3)	C11—C12—H12	121.2
C14—N5—H5'	123 (3)	N4—C13—C12	123.1 (3)
N2—C1—N1	111.6 (3)	N4—C13—H13	118.4
N2—C1—C4	122.3 (3)	C12—C13—H13	118.4
N1—C1—C4	125.9 (3)	N5—C14—C15	118.5 (4)
N1—C2—C3	104.9 (3)	N5—C14—C3	119.5 (4)
N1—C2—C9	121.2 (3)	C15—C14—C3	122.0 (4)
C3—C2—C9	133.8 (3)	C16—C15—C14	119.6 (4)
N2—C3—C2	110.0 (3)	C16—C15—H15	120.2
N2—C3—C14	116.5 (3)	C14—C15—H15	120.2
C2—C3—C14	133.5 (4)	C15—C16—C17	120.0 (4)
N3—C4—C5	122.6 (4)	C15—C16—H16	120.0
N3—C4—C1	117.4 (3)	C17—C16—H16	120.0
C5—C4—C1	120.0 (3)	C18—C17—C16	118.8 (4)
C6—C5—C4	118.9 (4)	C18—C17—H17	120.6
C6—C5—H5	120.5	C16—C17—H17	120.6
C4—C5—H5	120.5	N5—C18—C17	120.5 (4)
C7—C6—C5	118.8 (4)	N5—C18—H18	119.7
C7—C6—H6	120.6	C17—C18—H18	119.7
C5—C6—H6	120.6	N6—C19—Pt1	178.6 (3)
C6—C7—C8	119.6 (5)	N7—C20—Pt1	178.8 (3)
C6—C7—H7	120.2	H31A—O31—H31B	107.2 (12)
C8—C7—H7	120.2	H32A—O32—H32B	106.3 (12)
N3—C8—C7	122.7 (4)
C3—N2—C1—N1	0.4 (4)	C13—N4—C9—C10	−0.4 (5)
C3—N2—C1—C4	176.7 (3)	C13—N4—C9—C2	178.1 (3)
C2—N1—C1—N2	0.4 (4)	N1—C2—C9—N4	168.6 (3)
C2—N1—C1—C4	−175.8 (3)	C3—C2—C9—N4	−17.0 (5)
C1—N1—C2—C3	−0.9 (4)	N1—C2—C9—C10	−12.9 (5)
C1—N1—C2—C9	175.0 (3)	C3—C2—C9—C10	161.5 (4)
C1—N2—C3—C2	−1.0 (4)	N4—C9—C10—C11	1.1 (5)
C1—N2—C3—C14	179.5 (3)	C2—C9—C10—C11	−177.4 (3)
N1—C2—C3—N2	1.2 (4)	C9—C10—C11—C12	−0.7 (5)
C9—C2—C3—N2	−173.9 (3)	C10—C11—C12—C13	−0.3 (5)
N1—C2—C3—C14	−179.4 (4)	C9—N4—C13—C12	−0.7 (5)
C9—C2—C3—C14	5.5 (7)	C11—C12—C13—N4	1.0 (5)
C8—N3—C4—C5	−1.4 (5)	C18—N5—C14—C15	0.8 (6)
C8—N3—C4—C1	176.1 (3)	C18—N5—C14—C3	−179.9 (3)
N2—C1—C4—N3	−168.9 (3)	N2—C3—C14—N5	−173.1 (3)
N1—C1—C4—N3	6.9 (5)	C2—C3—C14—N5	7.4 (6)
N2—C1—C4—C5	8.7 (5)	N2—C3—C14—C15	6.1 (5)
N1—C1—C4—C5	−175.5 (3)	C2—C3—C14—C15	−173.3 (4)
N3—C4—C5—C6	2.5 (5)	N5—C14—C15—C16	0.1 (5)
C1—C4—C5—C6	−175.0 (3)	C3—C14—C15—C16	−179.1 (4)
C4—C5—C6—C7	−1.0 (6)	C14—C15—C16—C17	−0.7 (5)
C5—C6—C7—C8	−1.4 (7)	C15—C16—C17—C18	0.3 (6)
C4—N3—C8—C7	−1.1 (6)	C14—N5—C18—C17	−1.2 (6)
C6—C7—C8—N3	2.6 (7)	C16—C17—C18—N5	0.6 (6)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5′···N4	0.84	1.83	2.609 (4)	154
N1—H1′···O31^ii	0.84	1.94	2.771 (4)	169
O31—H31B···O32^iii	0.84	2.02	2.778 (4)	151
O32—H32A···N6^i	0.84	2.12	2.937 (4)	164
O31—H31A···N3^iv	0.84	2.05	2.822 (5)	152
O32—H32B···N7^v	0.84	2.02	2.854 (5)	170
C6—H6···O32^vi	0.95	2.68	3.564 (5)	155
C17—H17···O32^vii	0.95	2.88	3.459 (5)	120
C18—H18···O32^vii	0.95	2.70	3.375 (5)	129
C18—H18···N6^viii	0.95	2.50	3.406 (5)	161

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