4-Dimethylaminopyridinium 2,4-dinitrophenolate: supramolecular aggregation through N-H...O, C-H...O, C-H...[pi] and [pi]-[pi] interactions

Within and between mol­ecules of the title compound, C₇H₁₁N₂⁺·C₆H₃N₂O₅^-, there are N-H...O and C-H...O interactions which generate rings of motifs S(5), D, D₁²(4), R₂¹(7), R₂¹(5), R₁²(6), R₂²(10) and R₂²(14). The supramolecular aggregation is completed by the presence of C-H...[pi] and [pi]-[pi] interactions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.067
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.798
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda               -0.1862
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.6763
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.68
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   N2       =       5.28 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C7       =       2.99 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The design of organic polar crystals for quadratic non-linear optical (NLO) applications is supported by the observation that organic molecules containing π-electron systems asymmetrized by electron-donor and -acceptor groups are highly polarizable entities in which problems of transparency and crystal growth may arise from their molecular crystal packing (Pecaut & Bagieu-Beucher, 1993). It is known that nitrophenols act not only as π-acceptors to form various π-stacking complexes with other aromatic molecules, but also as acidic ligands to form salts through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). The bonding of electron-donor acceptor complexes depends strongly on the nature of the partners. The linkage could involve not only electrostatic interactions, but also the formation of molecular complexes (Zadrenko et al., 1997). It has been reported that proton-transferred thermochromic complexes are formed between phenols and amines in apolar solvents at low temperature if an appropriate hydrogen-bonding network between phenols and amines is present to stabilize it (Mizutani et al., 1998). Pyridinium picrate has been reported in two crystalline phases and it appears in both phases as an internally linked hydrogen-bonded ion pair. These two phases are termed molecular crystals rather than salts, based on their structural arrangements (Botoshansky et al., 1994). A similar structural arrangement has also been reported for 4-dimethylaminopyridinium picrate (Vembu, Nallu, Garrison & Youngs, 2003). The reaction of 4-nitrophenol with 4-dimethylaminopyridine results in the formation of a new NLO material, the crystal structure of which has been reported at room temperature (Evans et al., 1998). Recently, we have reported the crystal structure of 4-dimethylaminopyridinium 4-nitrophenolate 4-nitrophenol (1/1/1) at 120 K (Vembu, Nallu, Spencer & Howard, 2003). The X-ray structure determination of the title compound, (I), has been undertaken to study the nature of the interaction between 4-dimethylaminopyridine and 2,4-dinitrophenol in the solid state. This study may serve as a forerunner for assessing the optical properties of (I).

The asymmetric unit of (I) contains one 4-dimethylaminopyridinium cation and one 2,4-dinitrophenolate anion (Fig. 1). The bond lengths and angles of the phenolate and dimethylaminopyridinium moieties (Table 1) are comparable with those found in related structures reported in the Cambridge Structural Database (Version 5.23; Allen, 2002; Bruno et al., 2002).

The crystal structure of (I) is stabilized by N—H···O and C—H···O interactions. The range of H···O distances (Table 2) found in (I) agrees with those found for N—H···O (Jeffrey, 1997) and C—H···O hydrogen bonds (Desiraju & Steiner, 1999). As shown in Fig. 2, each of the C3—H3···O3, C3—H3···O4 and C5—H5···O5 interactions generates an S(5) ring motif (Etter, 1990; Bernstein et al., 1995). The S(5) rings generated by the C3—H3···O4 and C5—H5···O5 interactions are planar, whereas that generated by the C3—H3···O3 interaction is distorted from planarity, as atom O3 deviates by −0.284 (5) Å from the mean plane. The C3—H3···O3 and C3—H3···O4 interactions together constitute a pair of bifurcated donor bonds. The C12–H12C···O5 interaction generates a D motif linking the 4-dimethylaminopyridinium and 2,4-dinitrophenolate moieties together. The C13—H13A···O4 and C13—H13A···O5 interactions constitute a pair of bifurcated donor bonds generating a symmetrical three-centred hydrogen-bonded chelate (Desiraju, 1989) motif of graph set D₁²(4).

As seen from Fig. 3, the C12—H12B···O4ⁱ and C10—H10···O4ⁱ interactions constitute a pair of bifurcated acceptor bonds generating an R₂¹(7) motif. The C11—H11···O1ⁱⁱ and N3—H3A···O1ⁱⁱ interactions constitute a pair of bifurcated acceptor bonds generating an R₂¹(5) motif. The C7—H7···O2ⁱⁱ and N3—H3A···O2ⁱⁱ interactions constitute another pair of bifurcated acceptor bonds generating an R₂¹(5) motif. The N3—H3A···O1ⁱⁱ and N3—H3A···O2ⁱⁱ interactions constitute a pair of bifurcated donor bonds generating an R₁(²6) motif. The C7—H7···O2ⁱⁱ and C11—H11···O1ⁱⁱ interactions together generate an R₂²(10) motif. The C8—H8···O3ⁱⁱⁱ and C13—H13B···O3ⁱⁱⁱ interactions together generate a pair of bifurcated acceptor bonds generating an R₂¹(7) motif. The C12—H12B···O4^iv and C11—H11···O3^iv interactions together generate an R₂²(14) motif. There are several other weak C—H···O interactions and a C—H···π interaction, which contribute to the supramolecular aggregation of (I) (Table 2).

In the crystal structure of (I) (Fig. 4), the molecules are stacked in layers held together by pairs of π–π interactions, with a distance of 3.697 (1) Å between the centroids of the pyridinium ring and the benzene ring of the inversion-related 2,4-dinitrophenolate at (1 − x, 1 − y, 1 − z), and a distance of 3.561 (1) Å between the centroids of the benzene rings at (x, y, z) and (1 − x, 2 − y, −z). The interplay of strong N—H···O and weak C—H···O, C—H···π and π–π interactions with different strengths, directional preferences and distance fall of properties presents a complex mosaic of interactions. The three-dimensional arrangement of 2,4-dinitrophenolate and 4-dimethylaminopyridinium moieties in the unit cell shows that (I) is an internally linked hydrogen-bonded ion pair, and hence can be regarded as a molecular crystal rather than a salt.

S2. Experimental

4-Dimethylaminopyridine (4.9 mmol) in ethanol (25 ml) was added to 2,4-dinitrophenol (4.9 mmol) dissolved in ethanol (25 ml). The precipitate, (I) (3.9 mmol, yield 79%), was filtered and recrystallized from a 1:1 mixture of petroleum ether and acetone.

S3. Refinement

All H atoms were located from difference Fourier maps and their positional parameters were refined, with U_iso(H) = 1.2U_eq(parent atom). The C—H bond lengths are in the range 0.95 (2)–1.03 (2) Å.

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. Hydrogen bonds 1–6 (the numbers correspond to the sequence of entries in Table 2).
	Fig. 3. Hydrogen bonds 7–12 and 14–20 (the numbers correspond to sequence of entries in Table 2). Symmetry codes are as in Table 2.
	Fig. 4. Packing of the molecules in the unit cell of (I), viewed along the a axis, showing the N—H···O, C—H···O, C—H···π and π–π interactions.

4-Dimethylaminopyridinium 2,4-dinitrophenolate

Crystal data

C7H11N2^+·C6H3N2O5^−	Z = 2
Mr = 306.28	F(000) = 320
Triclinic, P1	Dx = 1.528 Mg m^−3
Hall symbol: -P 1	Melting point = 432–434 K
a = 7.7246 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1665 (10) Å	Cell parameters from 763 reflections
c = 10.8838 (13) Å	θ = 2.6–27.0°
α = 96.916 (3)°	µ = 0.12 mm^−1
β = 92.630 (3)°	T = 120 K
γ = 101.618 (3)°	Block, yellow
V = 665.88 (14) Å^3	0.15 × 0.15 × 0.12 mm

Data collection

Bruker Proteum M diffractometer	1444 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
Detector resolution: 8 pixels mm^-1	h = −9→8
ω scans	k = −9→9
3781 measured reflections	l = −12→11
2332 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	Only H-atom coordinates refined
S = 0.80	w = 1/[σ^2(Fo^2) + (0.0204P)^2] where P = (Fo^2 + 2Fc^2)/3
2332 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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
C1	0.2278 (2)	0.8980 (2)	−0.05184 (18)	0.0163 (5)
C2	0.2907 (2)	1.0056 (2)	0.06227 (19)	0.0163 (5)
C3	0.3875 (2)	0.9562 (2)	0.1562 (2)	0.0169 (5)
H3	0.427 (2)	1.031 (2)	0.2309 (18)	0.020*
C4	0.4256 (2)	0.7976 (2)	0.14274 (19)	0.0168 (5)
C5	0.3647 (2)	0.6838 (2)	0.03448 (19)	0.0182 (5)
H5	0.390 (2)	0.571 (2)	0.0307 (17)	0.022*
C6	0.2715 (3)	0.7336 (2)	−0.0571 (2)	0.0195 (5)
H6	0.234 (2)	0.658 (2)	−0.1317 (18)	0.023*
N1	0.2543 (2)	1.17279 (19)	0.08717 (17)	0.0195 (4)
N2	0.5283 (2)	0.7486 (2)	0.24042 (17)	0.0223 (4)
O1	0.14054 (17)	0.93398 (15)	−0.14207 (13)	0.0216 (4)
O2	0.20170 (18)	1.23992 (16)	0.00035 (13)	0.0255 (4)
O3	0.27575 (18)	1.24511 (16)	0.19526 (13)	0.0281 (4)
O4	0.57560 (18)	0.84841 (17)	0.33730 (14)	0.0280 (4)
O5	0.56493 (18)	0.60752 (17)	0.22452 (13)	0.0294 (4)
C7	1.0031 (2)	0.3307 (2)	0.7855 (2)	0.0188 (5)
H7	1.062 (2)	0.389 (2)	0.8654 (18)	0.023*
C8	0.9177 (3)	0.4063 (2)	0.7045 (2)	0.0190 (5)
H8	0.911 (2)	0.523 (2)	0.7243 (17)	0.023*
C9	0.8367 (2)	0.3143 (2)	0.59059 (19)	0.0170 (5)
C10	0.8427 (3)	0.1406 (2)	0.5708 (2)	0.0195 (5)
H10	0.785 (2)	0.068 (2)	0.4972 (18)	0.023*
C11	0.9318 (2)	0.0739 (3)	0.65571 (19)	0.0195 (5)
H11	0.941 (2)	−0.046 (2)	0.6486 (17)	0.023*
C12	0.6621 (3)	0.2839 (3)	0.3938 (2)	0.0262 (5)
H12C	0.622 (2)	0.363 (2)	0.3424 (19)	0.031*
H12B	0.558 (3)	0.199 (2)	0.4179 (19)	0.031*
H12A	0.739 (2)	0.223 (2)	0.3481 (18)	0.031*
C13	0.7444 (3)	0.5630 (3)	0.5297 (2)	0.0252 (6)
H13A	0.689 (2)	0.597 (2)	0.451 (2)	0.030*
H13B	0.672 (2)	0.581 (2)	0.5953 (19)	0.030*
H13C	0.861 (3)	0.641 (2)	0.5534 (19)	0.030*
N3	1.0129 (2)	0.1677 (2)	0.76077 (16)	0.0200 (4)
H3A	1.071 (3)	0.117 (2)	0.8151 (19)	0.024*
N4	0.7571 (2)	0.38617 (19)	0.50494 (15)	0.0203 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0136 (11)	0.0202 (11)	0.0155 (12)	0.0024 (9)	0.0026 (10)	0.0054 (10)
C2	0.0167 (11)	0.0146 (10)	0.0183 (13)	0.0041 (8)	0.0035 (10)	0.0028 (9)
C3	0.0141 (11)	0.0195 (11)	0.0153 (12)	0.0001 (9)	0.0032 (10)	0.0004 (9)
C4	0.0147 (11)	0.0197 (11)	0.0174 (12)	0.0040 (9)	0.0008 (10)	0.0075 (9)
C5	0.0183 (11)	0.0169 (11)	0.0209 (13)	0.0050 (9)	0.0032 (10)	0.0052 (10)
C6	0.0217 (12)	0.0166 (11)	0.0186 (13)	0.0023 (9)	0.0004 (10)	−0.0004 (10)
N1	0.0183 (9)	0.0205 (9)	0.0203 (11)	0.0053 (7)	0.0016 (8)	0.0022 (9)
N2	0.0199 (10)	0.0223 (10)	0.0258 (12)	0.0037 (8)	0.0021 (9)	0.0084 (9)
O1	0.0244 (8)	0.0209 (7)	0.0197 (9)	0.0064 (6)	−0.0049 (7)	0.0034 (7)
O2	0.0344 (9)	0.0213 (8)	0.0230 (9)	0.0106 (6)	−0.0042 (7)	0.0058 (7)
O3	0.0386 (9)	0.0256 (8)	0.0193 (9)	0.0121 (7)	−0.0036 (8)	−0.0071 (7)
O4	0.0315 (9)	0.0317 (8)	0.0199 (9)	0.0077 (7)	−0.0057 (7)	0.0012 (7)
O5	0.0343 (9)	0.0242 (8)	0.0331 (10)	0.0123 (7)	−0.0030 (8)	0.0093 (7)
C7	0.0179 (12)	0.0194 (11)	0.0179 (12)	0.0020 (9)	0.0002 (10)	0.0016 (10)
C8	0.0197 (11)	0.0176 (11)	0.0197 (13)	0.0042 (9)	0.0024 (10)	0.0015 (10)
C9	0.0145 (11)	0.0205 (11)	0.0165 (12)	0.0034 (9)	0.0027 (10)	0.0046 (10)
C10	0.0204 (12)	0.0221 (12)	0.0159 (13)	0.0047 (9)	0.0012 (10)	0.0011 (10)
C11	0.0203 (12)	0.0217 (11)	0.0175 (13)	0.0064 (9)	0.0046 (10)	0.0019 (10)
C12	0.0326 (14)	0.0317 (14)	0.0158 (13)	0.0129 (11)	−0.0038 (11)	0.0003 (11)
C13	0.0300 (14)	0.0229 (12)	0.0251 (15)	0.0119 (10)	−0.0005 (12)	0.0030 (11)
N3	0.0175 (10)	0.0236 (10)	0.0207 (11)	0.0066 (7)	0.0000 (8)	0.0071 (8)
N4	0.0262 (10)	0.0205 (9)	0.0149 (10)	0.0076 (8)	−0.0004 (9)	0.0015 (8)

Geometric parameters (Å, º)

C1—O1	1.262 (2)	C7—H7	0.983 (18)
C1—C2	1.435 (3)	C8—C9	1.417 (3)
C1—C6	1.444 (2)	C8—H8	0.968 (17)
C2—C3	1.385 (3)	C9—N4	1.347 (2)
C2—N1	1.445 (2)	C9—C10	1.420 (3)
C3—C4	1.378 (2)	C10—C11	1.356 (3)
C3—H3	0.954 (17)	C10—H10	0.968 (17)
C4—C5	1.408 (3)	C11—N3	1.348 (2)
C4—N2	1.440 (2)	C11—H11	0.989 (17)
C5—C6	1.352 (3)	C12—N4	1.459 (3)
C5—H5	0.977 (17)	C12—H12C	0.990 (19)
C6—H6	0.954 (17)	C12—H12B	1.02 (2)
N1—O3	1.2393 (19)	C12—H12A	0.968 (19)
N1—O2	1.240 (2)	C13—N4	1.461 (3)
N2—O5	1.2354 (18)	C13—H13A	1.03 (2)
N2—O4	1.2438 (19)	C13—H13B	0.94 (2)
C7—N3	1.344 (2)	C13—H13C	0.993 (18)
C7—C8	1.355 (3)	N3—H3A	0.913 (19)
O1—C1—C2	126.52 (18)	C9—C8—H8	119.4 (11)
O1—C1—C6	119.97 (17)	N4—C9—C8	122.37 (17)
C2—C1—C6	113.51 (17)	N4—C9—C10	121.13 (18)
C3—C2—C1	122.66 (18)	C8—C9—C10	116.50 (18)
C3—C2—N1	115.55 (18)	C11—C10—C9	119.7 (2)
C1—C2—N1	121.79 (17)	C11—C10—H10	118.9 (10)
C4—C3—C2	120.04 (19)	C9—C10—H10	121.3 (10)
C4—C3—H3	119.5 (10)	N3—C11—C10	121.7 (2)
C2—C3—H3	120.4 (10)	N3—C11—H11	113.9 (10)
C3—C4—C5	120.46 (19)	C10—C11—H11	124.4 (10)
C3—C4—N2	119.48 (18)	N4—C12—H12C	106.5 (11)
C5—C4—N2	120.06 (18)	N4—C12—H12B	109.8 (11)
C6—C5—C4	119.05 (19)	H12C—C12—H12B	111.5 (15)
C6—C5—H5	123.3 (10)	N4—C12—H12A	110.8 (11)
C4—C5—H5	117.6 (10)	H12C—C12—H12A	109.9 (17)
C5—C6—C1	124.26 (19)	H12B—C12—H12A	108.3 (15)
C5—C6—H6	118.9 (11)	N4—C13—H13A	108.9 (11)
C1—C6—H6	116.8 (11)	N4—C13—H13B	111.4 (12)
O3—N1—O2	121.66 (16)	H13A—C13—H13B	107.9 (16)
O3—N1—C2	118.94 (17)	N4—C13—H13C	113.2 (11)
O2—N1—C2	119.40 (17)	H13A—C13—H13C	108.7 (17)
O5—N2—O4	122.57 (17)	H13B—C13—H13C	106.5 (17)
O5—N2—C4	118.19 (17)	C7—N3—C11	120.24 (19)
O4—N2—C4	119.24 (17)	C7—N3—H3A	121.3 (12)
N3—C7—C8	121.3 (2)	C11—N3—H3A	118.4 (12)
N3—C7—H7	115.0 (10)	C9—N4—C12	120.52 (17)
C8—C7—H7	123.6 (10)	C9—N4—C13	120.30 (17)
C7—C8—C9	120.33 (19)	C12—N4—C13	118.69 (17)
C7—C8—H8	120.2 (11)
O1—C1—C2—C3	−179.3 (2)	C3—C4—N2—O5	−177.97 (17)
C6—C1—C2—C3	1.5 (3)	C5—C4—N2—O5	2.1 (3)
O1—C1—C2—N1	1.6 (3)	C3—C4—N2—O4	2.5 (3)
C6—C1—C2—N1	−177.59 (17)	C5—C4—N2—O4	−177.40 (18)
C1—C2—C3—C4	−0.6 (3)	N3—C7—C8—C9	−0.2 (3)
N1—C2—C3—C4	178.51 (16)	C7—C8—C9—N4	−177.1 (2)
C2—C3—C4—C5	−0.9 (3)	C7—C8—C9—C10	3.2 (3)
C2—C3—C4—N2	179.21 (19)	N4—C9—C10—C11	176.5 (2)
C3—C4—C5—C6	1.4 (3)	C8—C9—C10—C11	−3.8 (3)
N2—C4—C5—C6	−178.7 (2)	C9—C10—C11—N3	1.4 (3)
C4—C5—C6—C1	−0.4 (3)	C8—C7—N3—C11	−2.4 (3)
O1—C1—C6—C5	179.8 (2)	C10—C11—N3—C7	1.8 (3)
C2—C1—C6—C5	−1.0 (3)	C8—C9—N4—C12	−174.7 (2)
C3—C2—N1—O3	−15.2 (3)	C10—C9—N4—C12	5.0 (3)
C1—C2—N1—O3	163.95 (17)	C8—C9—N4—C13	−2.9 (3)
C3—C2—N1—O2	165.18 (18)	C10—C9—N4—C13	176.84 (19)
C1—C2—N1—O2	−15.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.954 (17)	2.350 (16)	2.665 (2)	98.6 (12)
C3—H3···O4	0.954 (17)	2.421 (17)	2.728 (3)	98.3 (11)
C5—H5···O5	0.977 (17)	2.406 (17)	2.732 (2)	98.8 (11)
C12—H12C···O5	0.990 (19)	2.60 (2)	3.576 (3)	170.0 (14)
C13—H13A···O4	1.03 (2)	2.78 (2)	3.697 (3)	147.9 (14)
C13—H13A···O5	1.03 (2)	2.62 (2)	3.628 (3)	164.5 (14)
C12—H12C···O3^i	0.990 (19)	2.972 (18)	3.541 (3)	117.6 (13)
C12—H12B···O4^i	1.02 (2)	2.920 (18)	3.457 (3)	113.6 (13)
C10—H10···O4^i	0.968 (17)	2.585 (18)	3.533 (2)	166.3 (15)
C5—H5···O2^i	0.977 (17)	2.772 (17)	3.558 (2)	137.9 (13)
C11—H11···O1^ii	0.989 (17)	2.731 (17)	3.126 (2)	104.3 (11)
C7—H7···O2^ii	0.983 (18)	2.369 (17)	2.986 (3)	120.2 (12)
N3—H3A···O1^ii	0.913 (19)	1.791 (19)	2.624 (2)	150.4 (17)
N3—H3A···O2^ii	0.913 (19)	2.238 (19)	2.865 (2)	125.4 (15)
C8—H8···O3^iii	0.968 (17)	2.688 (18)	3.555 (2)	149.3 (14)
C13—H13B···O3^iii	0.94 (2)	2.51 (2)	3.233 (3)	133.8 (14)
C12—H12B···O4^iv	1.02 (2)	2.94 (2)	3.683 (3)	130.3 (13)
C11—H11···O3^iv	0.989 (17)	2.858 (18)	3.401 (3)	115.3 (13)
C12—H12A···O1^v	0.968 (19)	2.74 (2)	3.646 (3)	156.1 (15)
C13—H13C···Cg1^vi	0.993 (18)	3.22 (2)	3.745 (2)	114.4 (14)

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