Crystal structure of difenoconazole.

In the title compound difenoconazole [systematic name: 1-({2-[2-chloro-4-(4-chloro-phen-oxy)phen-yl]-4-methyl-1,3-dioxolan-2-yl}meth-yl)-1H-1,2,4-triazole], C19H17Cl2N3O3, the dihedral angle between the planes of the 4-chloro-phenyl and 2-chloro-phenyl rings is 79.34 (9)°, while the dihedral angle between the planes of the triazole ring and the dioxolanyl group is 59.45 (19)°. In the crystal, pairs of C-H⋯N hydrogen bonds link adjacent mol-ecules, forming dimers with R 2 (2)(6) loops. In addition, the dimers are linked by C-H⋯O hydrogen bonds, resulting in a three-dimensional architecture. Disorder was modeled for one C atom of the dioxolanyl group over two sets of sites with an occupancy ratio of 0.566 (17):0.434 (17).

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Dong et al. (2013 ▶); Mu et al. (2013 ▶). For a related crystal structure, see: Jeon et al. (2013 ▶).

Experimental

Crystal data

C19H17Cl2N3O3

M = 406.26

Monoclinic,

a = 25.6913 (13) Å

b = 10.0220 (4) Å

c = 14.6417 (6) Å

β = 93.439 (4)°

V = 3763.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 173 K

0.50 × 0.42 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.837, T max = 0.885

28161 measured reflections

3694 independent reflections

3251 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.160

S = 1.06

3694 reflections

254 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814022429/hg5412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022429/hg5412Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814022429/hg5412Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814022429/hg5412fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. Only atoms of the major disorder components are shown.

Click here for additional data file.

. DOI: 10.1107/S1600536814022429/hg5412fig2.tif

Crystal packing of the title compound with C—H⋯N and C—H⋯O hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of hydrogen bonds. Only atoms of the major disorder components are shown.

CCDC reference: 1028719

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H17Cl2N3O3	F(000) = 1680
Mr = 406.26	Dx = 1.434 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9891 reflections
a = 25.6913 (13) Å	θ = 2.2–27.5°
b = 10.0220 (4) Å	µ = 0.37 mm−1
c = 14.6417 (6) Å	T = 173 K
β = 93.439 (4)°	Block, colourless
V = 3763.1 (3) Å3	0.50 × 0.42 × 0.34 mm
Z = 8

Bruker APEXII CCD diffractometer	3694 independent reflections
Radiation source: fine-focus sealed tube	3251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −31→31
Tmin = 0.837, Tmax = 0.885	k = −12→11
28161 measured reflections	l = −16→18

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0826P)2 + 11.4923P] where P = (Fo2 + 2Fc2)/3
3694 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.82 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.42744 (2)	0.49115 (6)	0.12241 (5)	0.0266 (2)
Cl2	0.82170 (3)	0.20023 (10)	0.20260 (9)	0.0669 (4)
O1	0.62242 (7)	0.48045 (19)	0.13830 (15)	0.0310 (5)
O2	0.39803 (7)	0.19880 (19)	0.13311 (13)	0.0278 (4)
O3	0.44578 (7)	0.04892 (18)	0.05807 (14)	0.0310 (5)
N1	0.35985 (8)	0.1646 (2)	−0.04986 (15)	0.0238 (5)
N2	0.35747 (10)	0.0522 (3)	−0.10262 (18)	0.0351 (6)
N3	0.27774 (9)	0.1059 (2)	−0.05524 (16)	0.0311 (5)
C1	0.48411 (10)	0.2656 (3)	0.08715 (18)	0.0234 (5)
C2	0.48477 (10)	0.4006 (2)	0.11281 (17)	0.0217 (5)
C3	0.53104 (10)	0.4691 (3)	0.13124 (17)	0.0232 (5)
H3	0.5305	0.5600	0.1496	0.028*
C4	0.57807 (10)	0.4041 (3)	0.12269 (18)	0.0241 (5)
C5	0.57897 (10)	0.2708 (3)	0.09724 (19)	0.0280 (6)
H5	0.6112	0.2260	0.0917	0.034*
C6	0.53236 (10)	0.2042 (3)	0.08011 (19)	0.0274 (6)
H6	0.5332	0.1129	0.0628	0.033*
C7	0.66965 (10)	0.4125 (3)	0.15259 (19)	0.0246 (5)
C8	0.70587 (12)	0.4212 (3)	0.0878 (2)	0.0368 (7)
H8	0.6985	0.4704	0.0331	0.044*
C9	0.75346 (12)	0.3571 (3)	0.1033 (3)	0.0446 (8)
H9	0.7792	0.3625	0.0596	0.054*
C10	0.76287 (11)	0.2854 (3)	0.1831 (2)	0.0372 (7)
C11	0.72675 (12)	0.2774 (3)	0.2478 (2)	0.0337 (7)
H11	0.7339	0.2273	0.3022	0.040*
C12	0.67983 (11)	0.3430 (3)	0.23296 (19)	0.0308 (6)
H12	0.6547	0.3404	0.2779	0.037*
C13	0.43413 (10)	0.1863 (2)	0.06428 (18)	0.0235 (5)
C14	0.39958 (15)	0.0777 (3)	0.1848 (2)	0.0465 (8)
H14A	0.3646	0.0559	0.2053	0.056*	0.566 (17)
H14B	0.4241	0.0860	0.2393	0.056*	0.566 (17)
H14C	0.4047	0.0970	0.2510	0.056*	0.434 (17)
H14D	0.3666	0.0274	0.1738	0.056*	0.434 (17)
C15	0.4172 (4)	−0.0259 (7)	0.1230 (6)	0.042 (3)	0.566 (17)
H15	0.3851	−0.0594	0.0883	0.064*	0.566 (17)
C15'	0.4417 (4)	0.0044 (8)	0.1547 (6)	0.040 (3)	0.434 (17)
H15'	0.4736	0.0383	0.1899	0.059*	0.434 (17)
C16	0.4442 (2)	−0.1428 (4)	0.1591 (3)	0.0714 (13)
H16A	0.4771	−0.1534	0.1293	0.107*	0.566 (17)
H16B	0.4223	−0.2218	0.1472	0.107*	0.566 (17)
H16C	0.4514	−0.1325	0.2252	0.107*	0.566 (17)
H16D	0.4503	−0.1784	0.0983	0.107*	0.434 (17)
H16E	0.4111	−0.1777	0.1792	0.107*	0.434 (17)
H16F	0.4727	−0.1699	0.2025	0.107*	0.434 (17)
C17	0.40879 (10)	0.2322 (3)	−0.02759 (18)	0.0245 (5)
H17A	0.4026	0.3296	−0.0254	0.029*
H17B	0.4330	0.2148	−0.0764	0.029*
C18	0.31254 (10)	0.1939 (3)	−0.02307 (18)	0.0248 (5)
H18	0.3048	0.2680	0.0142	0.030*
C19	0.30749 (12)	0.0227 (3)	−0.1031 (2)	0.0357 (7)
H19	0.2932	−0.0524	−0.1351	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0242 (3)	0.0184 (3)	0.0374 (4)	0.0054 (2)	0.0048 (3)	−0.0025 (2)
Cl2	0.0336 (5)	0.0520 (6)	0.1140 (9)	0.0139 (4)	−0.0048 (5)	0.0196 (5)
O1	0.0219 (9)	0.0197 (10)	0.0513 (13)	−0.0017 (7)	0.0017 (8)	0.0011 (8)
O2	0.0288 (10)	0.0241 (10)	0.0310 (10)	0.0005 (8)	0.0061 (8)	0.0041 (7)
O3	0.0271 (10)	0.0141 (9)	0.0518 (13)	0.0024 (7)	0.0020 (8)	−0.0014 (8)
N1	0.0232 (11)	0.0182 (11)	0.0298 (12)	0.0005 (8)	0.0003 (8)	−0.0026 (8)
N2	0.0320 (13)	0.0267 (13)	0.0462 (15)	0.0009 (10)	0.0000 (11)	−0.0134 (11)
N3	0.0256 (12)	0.0322 (13)	0.0350 (13)	−0.0012 (10)	−0.0010 (9)	0.0043 (10)
C1	0.0239 (13)	0.0178 (12)	0.0283 (13)	0.0020 (10)	0.0007 (10)	0.0001 (10)
C2	0.0234 (12)	0.0173 (12)	0.0247 (13)	0.0045 (10)	0.0039 (10)	0.0013 (9)
C3	0.0271 (13)	0.0150 (12)	0.0278 (13)	0.0011 (10)	0.0036 (10)	0.0015 (10)
C4	0.0231 (13)	0.0210 (13)	0.0280 (13)	−0.0014 (10)	0.0013 (10)	0.0025 (10)
C5	0.0240 (13)	0.0230 (14)	0.0370 (15)	0.0055 (10)	0.0004 (11)	−0.0014 (11)
C6	0.0261 (13)	0.0181 (13)	0.0377 (15)	0.0032 (10)	0.0000 (11)	−0.0027 (10)
C7	0.0193 (12)	0.0183 (12)	0.0359 (14)	−0.0016 (10)	0.0004 (10)	−0.0001 (10)
C8	0.0359 (16)	0.0347 (16)	0.0406 (17)	0.0062 (13)	0.0089 (13)	0.0149 (13)
C9	0.0311 (16)	0.0447 (19)	0.060 (2)	0.0059 (14)	0.0187 (14)	0.0165 (16)
C10	0.0263 (14)	0.0254 (15)	0.059 (2)	0.0010 (11)	−0.0044 (13)	0.0050 (13)
C11	0.0417 (16)	0.0247 (14)	0.0331 (15)	−0.0042 (12)	−0.0099 (12)	0.0021 (11)
C12	0.0369 (15)	0.0255 (14)	0.0303 (14)	−0.0037 (12)	0.0047 (11)	−0.0011 (11)
C13	0.0236 (12)	0.0135 (12)	0.0336 (14)	0.0032 (10)	0.0036 (10)	−0.0013 (10)
C14	0.070 (2)	0.0269 (16)	0.0443 (19)	−0.0014 (16)	0.0185 (16)	0.0100 (13)
C15	0.044 (5)	0.025 (3)	0.059 (5)	−0.004 (3)	0.011 (4)	0.009 (3)
C15'	0.040 (5)	0.023 (4)	0.052 (5)	−0.012 (3)	−0.023 (4)	0.007 (3)
C16	0.106 (4)	0.035 (2)	0.074 (3)	0.006 (2)	0.008 (3)	0.0103 (19)
C17	0.0224 (12)	0.0213 (13)	0.0300 (14)	−0.0023 (10)	0.0038 (10)	−0.0015 (10)
C18	0.0233 (12)	0.0229 (13)	0.0281 (13)	0.0023 (10)	0.0012 (10)	0.0018 (10)
C19	0.0316 (15)	0.0247 (15)	0.0497 (18)	−0.0032 (12)	−0.0065 (13)	−0.0059 (12)

Cl1—C2	1.743 (2)	C8—H8	0.9500
Cl2—C10	1.744 (3)	C9—C10	1.380 (5)
O1—C4	1.380 (3)	C9—H9	0.9500
O1—C7	1.396 (3)	C10—C11	1.367 (5)
O2—C13	1.416 (3)	C11—C12	1.379 (4)
O2—C14	1.429 (4)	C11—H11	0.9500
O3—C13	1.413 (3)	C12—H12	0.9500
O3—C15	1.445 (6)	C13—C17	1.530 (4)
O3—C15'	1.493 (9)	C14—C15'	1.401 (10)
N1—C18	1.332 (3)	C14—C15	1.467 (8)
N1—N2	1.365 (3)	C14—H14A	0.9900
N1—C17	1.448 (3)	C14—H14B	0.9900
N2—C19	1.317 (4)	C14—H14C	0.9900
N3—C18	1.322 (4)	C14—H14D	0.9900
N3—C19	1.354 (4)	C15—C16	1.445 (8)
C1—C6	1.394 (4)	C15—H15	1.0000
C1—C2	1.404 (4)	C15'—C16	1.478 (9)
C1—C13	1.530 (3)	C15'—H15'	1.0000
C2—C3	1.385 (4)	C16—H16A	0.9800
C3—C4	1.385 (4)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C4—C5	1.387 (4)	C16—H16D	0.9800
C5—C6	1.381 (4)	C16—H16E	0.9800
C5—H5	0.9500	C16—H16F	0.9800
C6—H6	0.9500	C17—H17A	0.9900
C7—C8	1.371 (4)	C17—H17B	0.9900
C7—C12	1.379 (4)	C18—H18	0.9500
C8—C9	1.388 (4)	C19—H19	0.9500
C4—O1—C7	117.1 (2)	O2—C14—H14C	110.5
C13—O2—C14	107.6 (2)	C15—C14—H14C	135.6
C13—O3—C15	110.2 (3)	H14A—C14—H14C	79.4
C13—O3—C15'	101.7 (4)	H14B—C14—H14C	32.2
C15—O3—C15'	32.3 (3)	C15'—C14—H14D	110.5
C18—N1—N2	109.7 (2)	O2—C14—H14D	110.5
C18—N1—C17	128.8 (2)	C15—C14—H14D	80.3
N2—N1—C17	121.5 (2)	H14A—C14—H14D	32.1
C19—N2—N1	101.5 (2)	H14B—C14—H14D	132.1
C18—N3—C19	101.8 (2)	H14C—C14—H14D	108.7
C6—C1—C2	116.7 (2)	O3—C15—C16	114.2 (5)
C6—C1—C13	119.5 (2)	O3—C15—C14	103.1 (5)
C2—C1—C13	123.8 (2)	C16—C15—C14	120.5 (7)
C3—C2—C1	121.8 (2)	O3—C15—H15	106.0
C3—C2—Cl1	116.47 (19)	C16—C15—H15	106.0
C1—C2—Cl1	121.8 (2)	C14—C15—H15	106.0
C2—C3—C4	119.5 (2)	C14—C15'—C16	122.8 (8)
C2—C3—H3	120.3	C14—C15'—O3	103.9 (5)
C4—C3—H3	120.3	C16—C15'—O3	109.5 (6)
O1—C4—C3	116.1 (2)	C14—C15'—H15'	106.5
O1—C4—C5	123.5 (2)	C16—C15'—H15'	106.5
C3—C4—C5	120.4 (2)	O3—C15'—H15'	106.5
C6—C5—C4	119.1 (2)	C15—C16—C15'	32.5 (3)
C6—C5—H5	120.5	C15—C16—H16A	109.5
C4—C5—H5	120.5	C15'—C16—H16A	97.2
C5—C6—C1	122.6 (2)	C15—C16—H16B	109.5
C5—C6—H6	118.7	C15'—C16—H16B	140.9
C1—C6—H6	118.7	H16A—C16—H16B	109.5
C8—C7—C12	121.4 (3)	C15—C16—H16C	109.5
C8—C7—O1	119.0 (2)	C15'—C16—H16C	86.7
C12—C7—O1	119.5 (2)	H16A—C16—H16C	109.5
C7—C8—C9	119.0 (3)	H16B—C16—H16C	109.5
C7—C8—H8	120.5	C15—C16—H16D	93.6
C9—C8—H8	120.5	C15'—C16—H16D	109.5
C10—C9—C8	119.2 (3)	H16A—C16—H16D	50.7
C10—C9—H9	120.4	H16B—C16—H16D	70.5
C8—C9—H9	120.4	H16C—C16—H16D	154.7
C11—C10—C9	121.7 (3)	C15—C16—H16E	89.7
C11—C10—Cl2	118.4 (2)	C15'—C16—H16E	109.5
C9—C10—Cl2	120.0 (3)	H16A—C16—H16E	151.8
C10—C11—C12	119.1 (3)	H16B—C16—H16E	42.9
C10—C11—H11	120.5	H16C—C16—H16E	81.7
C12—C11—H11	120.5	H16D—C16—H16E	109.5
C7—C12—C11	119.6 (3)	C15—C16—H16F	141.8
C7—C12—H12	120.2	C15'—C16—H16F	109.5
C11—C12—H12	120.2	H16A—C16—H16F	68.1
O3—C13—O2	106.4 (2)	H16B—C16—H16F	106.8
O3—C13—C17	108.5 (2)	H16C—C16—H16F	45.4
O2—C13—C17	109.7 (2)	H16D—C16—H16F	109.5
O3—C13—C1	110.0 (2)	H16E—C16—H16F	109.5
O2—C13—C1	112.0 (2)	N1—C17—C13	112.0 (2)
C17—C13—C1	110.1 (2)	N1—C17—H17A	109.2
C15'—C14—O2	106.0 (4)	C13—C17—H17A	109.2
C15'—C14—C15	33.0 (3)	N1—C17—H17B	109.2
O2—C14—C15	105.9 (3)	C13—C17—H17B	109.2
C15'—C14—H14A	135.5	H17A—C17—H17B	107.9
O2—C14—H14A	110.6	N3—C18—N1	111.0 (2)
C15—C14—H14A	110.6	N3—C18—H18	124.5
C15'—C14—H14B	80.2	N1—C18—H18	124.5
O2—C14—H14B	110.6	N2—C19—N3	116.1 (3)
C15—C14—H14B	110.6	N2—C19—H19	122.0
H14A—C14—H14B	108.7	N3—C19—H19	122.0
C15'—C14—H14C	110.5
C18—N1—N2—C19	0.1 (3)	C6—C1—C13—O3	13.0 (3)
C17—N1—N2—C19	178.1 (2)	C2—C1—C13—O3	−169.0 (2)
C6—C1—C2—C3	−0.7 (4)	C6—C1—C13—O2	131.2 (2)
C13—C1—C2—C3	−178.8 (2)	C2—C1—C13—O2	−50.8 (3)
C6—C1—C2—Cl1	178.9 (2)	C6—C1—C13—C17	−106.5 (3)
C13—C1—C2—Cl1	0.8 (4)	C2—C1—C13—C17	71.5 (3)
C1—C2—C3—C4	1.2 (4)	C13—O2—C14—C15'	8.6 (6)
Cl1—C2—C3—C4	−178.40 (19)	C13—O2—C14—C15	−25.8 (6)
C7—O1—C4—C3	164.5 (2)	C13—O3—C15—C16	−147.7 (6)
C7—O1—C4—C5	−17.3 (4)	C15'—O3—C15—C16	−68.0 (10)
C2—C3—C4—O1	177.3 (2)	C13—O3—C15—C14	−15.2 (8)
C2—C3—C4—C5	−1.0 (4)	C15'—O3—C15—C14	64.5 (9)
O1—C4—C5—C6	−177.8 (2)	C15'—C14—C15—O3	−70.5 (8)
C3—C4—C5—C6	0.3 (4)	O2—C14—C15—O3	24.6 (8)
C4—C5—C6—C1	0.1 (4)	C15'—C14—C15—C16	58.2 (11)
C2—C1—C6—C5	0.0 (4)	O2—C14—C15—C16	153.3 (6)
C13—C1—C6—C5	178.2 (3)	O2—C14—C15'—C16	−153.1 (7)
C4—O1—C7—C8	111.7 (3)	C15—C14—C15'—C16	−58.4 (10)
C4—O1—C7—C12	−71.1 (3)	O2—C14—C15'—O3	−28.4 (8)
C12—C7—C8—C9	0.8 (5)	C15—C14—C15'—O3	66.2 (7)
O1—C7—C8—C9	178.0 (3)	C13—O3—C15'—C14	37.8 (7)
C7—C8—C9—C10	0.6 (5)	C15—O3—C15'—C14	−71.6 (9)
C8—C9—C10—C11	−0.9 (5)	C13—O3—C15'—C16	170.7 (6)
C8—C9—C10—Cl2	178.2 (3)	C15—O3—C15'—C16	61.3 (8)
C9—C10—C11—C12	−0.2 (5)	O3—C15—C16—C15'	68.7 (9)
Cl2—C10—C11—C12	−179.3 (2)	C14—C15—C16—C15'	−54.9 (11)
C8—C7—C12—C11	−2.0 (4)	C14—C15'—C16—C15	61.5 (10)
O1—C7—C12—C11	−179.1 (2)	O3—C15'—C16—C15	−60.7 (8)
C10—C11—C12—C7	1.6 (4)	C18—N1—C17—C13	83.7 (3)
C15—O3—C13—O2	−0.1 (6)	N2—N1—C17—C13	−94.0 (3)
C15'—O3—C13—O2	−32.6 (5)	O3—C13—C17—N1	62.6 (3)
C15—O3—C13—C17	−118.1 (6)	O2—C13—C17—N1	−53.3 (3)
C15'—O3—C13—C17	−150.5 (5)	C1—C13—C17—N1	−177.0 (2)
C15—O3—C13—C1	121.5 (5)	C19—N3—C18—N1	−0.2 (3)
C15'—O3—C13—C1	89.0 (5)	N2—N1—C18—N3	0.1 (3)
C14—O2—C13—O3	16.2 (3)	C17—N1—C18—N3	−177.8 (2)
C14—O2—C13—C17	133.3 (2)	N1—N2—C19—N3	−0.2 (4)
C14—O2—C13—C1	−104.1 (3)	C18—N3—C19—N2	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.48	3.314 (3)	146
C12—H12···O2ii	0.95	2.40	3.226 (3)	145
C17—H17A···O1iii	0.99	2.58	3.378 (3)	138
C18—H18···N3iv	0.95	2.57	3.323 (4)	136

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O3i	0.95	2.48	3.314(3)	146
C12H12O2ii	0.95	2.40	3.226(3)	145
C17H17AO1iii	0.99	2.58	3.378(3)	138
C18H18N3iv	0.95	2.57	3.323(4)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .