N′-[Bis(benzyl­sulfan­yl)methyl­ene]-2-furohydrazide

In the title compound, C₂₀H₁₈N₂O₂S₂, the dihedral angles between the 2-furoic acid group and the two benzyl groups are 72.4 (9) and 75.8 (8)°, while the angle between the mean planes of the two benzyl groups is 48.9 (2)°. The crystal packing is stabilized by inter­molecular C—H...O inter­actions between the extended O atom of a 2-furoic acid group and H atoms from nearby benzyl and 2-furoic acid groups in the unit cell, linking the mol­ecules into chains in a zigzag pattern, diagonally across the ac plane containing the 2-fuoric acid rings. Additional inter­molecular inter­actions occur between the π orbitals of one benzyl ring and H atoms from a nearby benzyl ring at the opposite end of the mol­ecule. Additional intra­molecular inter­actions between the hydrazide H atom and both an O atom from a nearby furoic acid group and an S atom from a close sulfanyl group provide added stability to the molecule.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.092
• Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found





Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.752     0.908
            Tmin(prime) and Tmax expected:      0.853     0.908
            RR(prime) =      0.882
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Dithiocarbazate derivatives have been widely studied in radiopharmaceutical applications (Boschi et al. 2003) and have potential biological activity as anticancer and antimicrobial drugs (Bharti et al. 2000). This functional group is of particular interest and can coordinate to metals to give structures with different geometries and properties. As a part of our ongoing research on the dithio derivatives of acid hydrazides, we report here the crystal structure of the title compound, C₂₀H₁₁₈N₂O₂S₂, a new bis benzyl sulfanyl methylene hydrazide.

The dihedral angle between the 2-furoic acid group and the two benzyl groups is 72.4 (9)° and 75.8 (8)°, respectively, while the angle between the mean planes of the two benzyl groups is 48.9 (2)° (Fig. 1). Bond angles around C1 clearly indicate planar sp² behavior. Crystal packing is stabilized by intermolecular C—H···O packing interactions between the extended oxygen atom (O1) of a 2-furoic acid group and hydrogen atoms, both from nearby benzyl (H4AA) and 2-furoic acid groups (H4A) in the unit cell, which link the molecules into chains in a zigzag-like pattern, diagonally across the ac plane containing the 2-furoic acid rings (Fig. 2). Additional intermolecular interactions occur between the Cg1-π orbitals of one benzyl ring and hydrogen atoms from a nearby benzyl ring at the opposite end of the molecule (Table 1). Additional intramolecular interactions between the hydrazide hydrogen atom (H2A) and both the oxygen from a nearby furoic acid group and a sulfur atom from a close sulfanyl group provide added stability.

Related literature

For a related structure, see: Boschi et al. (2003). For related background (biological, anticancer and antimicrobial activity), see: Bharti et al. (2000); Chan et al. (2003).

S2. Experimental

Potassium 2-furoic acid hydrazide carbodithioate was prepared by adding carbon disulfide (0.04 mol, 2.4 ml) to a solution of furan-2-carboxylic acid hydrazide (0.02 mol, 2.52 g) and potassium hydroxide (0.02 mol, 1.12 g) in methanol (30 ml) and stirring the reaction mixture for 2 h. The solid that separated was filtered off, washed with a 10% (v/v) mixture of ethanol-ether and dried in vacuo. yield 1.44 g, 60%, m.p. 438 K. The title ompound was prepared by drop wise addition of benzyl chloride (0.02 mol, 2.53 g) to a suspension of a potassium salt of 2-furoic acid hydrazide carbodithioate (0.01 mol, 2.28 g) in methanol (20 ml) and stirring the reaction mixture for a period of 5–6 h. The reaction mixture was filtered and the solution was evaporated almost to dryness. The solid was washed several times with carbon tetrachloride and then with chloroform and recrystalized from methanol. Transparent white shining crystals of the title compound (m.p. 388 K), suitable for X-ray analysis were obtained by slow evaporation of the methanol solution over a period of three weeks (yield 1.91 g, 50%): Analysis found: C 62.82, H 4.75, N 7.40, S 16.85; C₂₀H₁₈N₂O₂S₂ requires: C 62.74, H 4.70, N 7.32, S 16.73.

S3. Refinement

The amide hydrogen atom (H2A) was located in a difference Fourier map and along with all other H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.86 Å; C—H = 0.93 to 0.97 Å, and U_iso(H) = 1.18–1.22U_eq(C,N). The maximum residual electron density peaks of 0.486 and -0.297 e ų, were located at 0.68 Å from CA2 and 0.27 Å from H6A.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. Molecular structure of the title compound showing atom labeling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of C20H18N2O2S2, viewed down the b axis. Dashed lines indicate intermolecular hydrogen bonding.

N'-[Bis(benzylsulfanyl)methylene]-2-furohydrazide

Crystal data

C20H18N2O2S2	Z = 2
Mr = 382.48	F(000) = 400
Triclinic, P1	Dx = 1.397 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2058 (14) Å	Cell parameters from 8953 reflections
b = 9.2663 (14) Å	θ = 2.2–30.6°
c = 11.3877 (17) Å	µ = 0.31 mm^−1
α = 109.983 (2)°	T = 100 K
β = 94.781 (2)°	Prism, colorless
γ = 90.201 (3)°	0.50 × 0.48 × 0.31 mm
V = 909.2 (2) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	5473 independent reflections
Radiation source: fine-focus sealed tube	5150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ϕ and ω scans	θmax = 30.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −12→13
Tmin = 0.752, Tmax = 0.908	k = −13→13
10879 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.3812P] where P = (Fo^2 + 2Fc^2)/3
5473 reflections	(Δ/σ)max = 0.002
235 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR(KBr,ν cm^-1): 3310, (–NH); 1680, (C=O); 1583, (Thiomide I[β(NH + ν(CN)]; 1277, (Thioamide II [ν(CN) + β(NH)]; 754, (Thioamide IV, /n (C—S); 1074 /n (N—N). ¹H NMR (CDCl₃,δ, p.p.m.): 9.70, (s, 1H, NH); 4.25, (d, 2H, –CH₂); 7.76–7.89, (m, 3H, furan ring); 7.31–7.46, (m, 5H, phenyl); ¹³C NMR (CDCl₃, δ, p.p.m.): 178.61, (C—S); 160.30, (C=O); 145.40, (C3); 115.92, (C4); 112.52, (C5); 144.36, (C6); 153.12, (C2A); 112.34, (C3A,7 A); 129.76, (C4A,6 A); 127.78, (C5A); 36.86, (CH₂).

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
S1A	0.83197 (3)	0.46195 (3)	0.31516 (2)	0.01799 (7)
S1B	0.83350 (3)	0.69808 (3)	0.57280 (2)	0.01936 (7)
O1	1.31416 (9)	0.81929 (11)	0.44309 (8)	0.02540 (18)
O2	1.15179 (9)	1.05449 (10)	0.71366 (8)	0.02291 (17)
N1	1.03648 (10)	0.68224 (11)	0.41270 (8)	0.01901 (18)
N2	1.08610 (10)	0.81545 (11)	0.50926 (9)	0.01960 (18)
H2A	1.0290	0.8610	0.5657	0.024*
C1	0.91710 (12)	0.62306 (12)	0.43136 (9)	0.01711 (18)
C2	1.22268 (12)	0.87532 (12)	0.51658 (10)	0.01811 (19)
C3	1.25246 (12)	1.01706 (12)	0.62573 (10)	0.01824 (19)
C4	1.36458 (13)	1.12278 (13)	0.66080 (11)	0.0227 (2)
H4A	1.4459	1.1235	0.6177	0.027*
C5	1.33189 (15)	1.23308 (14)	0.77784 (12)	0.0270 (2)
H5A	1.3882	1.3201	0.8257	0.032*
C6	1.20373 (15)	1.18689 (14)	0.80570 (12)	0.0273 (2)
H6A	1.1575	1.2380	0.8773	0.033*
C1A	0.95464 (12)	0.43706 (14)	0.19310 (10)	0.0206 (2)
H1AA	0.9687	0.5337	0.1794	0.025*
H1AB	1.0488	0.4057	0.2190	0.025*
C2A	0.89122 (11)	0.31695 (12)	0.07338 (10)	0.01711 (19)
C3A	0.84726 (12)	0.35829 (13)	−0.03044 (10)	0.0194 (2)
H3AA	0.8530	0.4610	−0.0239	0.023*
C4A	0.79483 (13)	0.24774 (14)	−0.14391 (10)	0.0231 (2)
H4AA	0.7684	0.2762	−0.2133	0.028*
C5A	0.78214 (13)	0.09491 (14)	−0.15297 (11)	0.0247 (2)
H5AA	0.7470	0.0207	−0.2285	0.030*
C6A	0.82198 (13)	0.05301 (13)	−0.04922 (12)	0.0250 (2)
H6AA	0.8114	−0.0490	−0.0547	0.030*
C7A	0.87777 (13)	0.16316 (13)	0.06314 (11)	0.0217 (2)
H7AA	0.9063	0.1340	0.1318	0.026*
C1B	0.66064 (12)	0.59096 (14)	0.54544 (10)	0.0215 (2)
H1BA	0.5962	0.6137	0.4827	0.026*
H1BB	0.6758	0.4813	0.5174	0.026*
C2B	0.59769 (11)	0.64384 (12)	0.67084 (10)	0.01821 (19)
C3B	0.62147 (12)	0.56157 (13)	0.75201 (11)	0.0217 (2)
H3BA	0.6725	0.4712	0.7275	0.026*
C4B	0.56896 (13)	0.61435 (14)	0.87003 (11)	0.0234 (2)
H4BA	0.5854	0.5592	0.9242	0.028*
C5B	0.49201 (13)	0.74924 (14)	0.90733 (11)	0.0234 (2)
H5BA	0.4572	0.7843	0.9862	0.028*
C6B	0.46754 (13)	0.83113 (14)	0.82611 (11)	0.0235 (2)
H6BA	0.4158	0.9211	0.8505	0.028*
C7B	0.52029 (12)	0.77887 (13)	0.70825 (11)	0.0207 (2)
H7BA	0.5039	0.8342	0.6542	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.01715 (12)	0.02079 (13)	0.01268 (11)	−0.00613 (9)	0.00220 (9)	0.00130 (9)
S1B	0.01660 (12)	0.02282 (13)	0.01414 (12)	−0.00608 (9)	0.00312 (9)	0.00017 (9)
O1	0.0206 (4)	0.0314 (4)	0.0182 (4)	−0.0067 (3)	0.0048 (3)	0.0001 (3)
O2	0.0243 (4)	0.0205 (4)	0.0195 (4)	−0.0025 (3)	0.0052 (3)	0.0004 (3)
N1	0.0188 (4)	0.0197 (4)	0.0148 (4)	−0.0059 (3)	0.0013 (3)	0.0012 (3)
N2	0.0186 (4)	0.0192 (4)	0.0164 (4)	−0.0057 (3)	0.0042 (3)	−0.0003 (3)
C1	0.0178 (4)	0.0188 (4)	0.0126 (4)	−0.0030 (3)	0.0014 (3)	0.0027 (3)
C2	0.0182 (5)	0.0200 (5)	0.0150 (4)	−0.0044 (4)	0.0002 (4)	0.0048 (4)
C3	0.0184 (5)	0.0190 (5)	0.0163 (4)	−0.0025 (4)	0.0012 (4)	0.0048 (4)
C4	0.0226 (5)	0.0229 (5)	0.0209 (5)	−0.0069 (4)	−0.0016 (4)	0.0065 (4)
C5	0.0328 (6)	0.0196 (5)	0.0238 (5)	−0.0061 (4)	−0.0034 (5)	0.0028 (4)
C6	0.0348 (6)	0.0197 (5)	0.0212 (5)	−0.0008 (4)	0.0028 (5)	−0.0012 (4)
C1A	0.0184 (5)	0.0274 (5)	0.0131 (4)	−0.0067 (4)	0.0024 (4)	0.0032 (4)
C2A	0.0151 (4)	0.0206 (5)	0.0136 (4)	−0.0017 (3)	0.0033 (3)	0.0029 (4)
C3A	0.0215 (5)	0.0199 (5)	0.0158 (4)	−0.0022 (4)	0.0027 (4)	0.0049 (4)
C4A	0.0245 (5)	0.0277 (6)	0.0150 (5)	−0.0029 (4)	0.0006 (4)	0.0049 (4)
C5A	0.0228 (5)	0.0236 (5)	0.0198 (5)	−0.0034 (4)	0.0033 (4)	−0.0029 (4)
C6A	0.0244 (5)	0.0169 (5)	0.0303 (6)	0.0004 (4)	0.0055 (4)	0.0032 (4)
C7A	0.0212 (5)	0.0227 (5)	0.0222 (5)	0.0011 (4)	0.0026 (4)	0.0087 (4)
C1B	0.0172 (5)	0.0261 (5)	0.0162 (4)	−0.0073 (4)	0.0032 (4)	0.0003 (4)
C2B	0.0138 (4)	0.0210 (5)	0.0162 (4)	−0.0047 (3)	0.0022 (3)	0.0015 (4)
C3B	0.0190 (5)	0.0219 (5)	0.0228 (5)	0.0003 (4)	0.0043 (4)	0.0053 (4)
C4B	0.0216 (5)	0.0287 (6)	0.0204 (5)	−0.0018 (4)	0.0034 (4)	0.0089 (4)
C5B	0.0196 (5)	0.0282 (6)	0.0184 (5)	−0.0037 (4)	0.0055 (4)	0.0020 (4)
C6B	0.0190 (5)	0.0222 (5)	0.0256 (5)	0.0004 (4)	0.0066 (4)	0.0024 (4)
C7B	0.0175 (5)	0.0223 (5)	0.0218 (5)	−0.0018 (4)	0.0027 (4)	0.0065 (4)

Geometric parameters (Å, º)

S1A—C1	1.7500 (11)	C3A—C4A	1.3928 (15)
S1A—C1A	1.8179 (11)	C3A—H3AA	0.9300
S1B—C1	1.7648 (11)	C4A—C5A	1.3881 (17)
S1B—C1B	1.8192 (11)	C4A—H4AA	0.9300
O1—C2	1.2259 (14)	C5A—C6A	1.3868 (18)
O2—C6	1.3659 (14)	C5A—H5AA	0.9300
O2—C3	1.3789 (13)	C6A—C7A	1.3917 (17)
N1—C1	1.2915 (14)	C6A—H6AA	0.9300
N1—N2	1.3879 (12)	C7A—H7AA	0.9300
N2—C2	1.3571 (14)	C1B—C2B	1.5090 (15)
N2—H2A	0.8600	C1B—H1BA	0.9700
C2—C3	1.4731 (15)	C1B—H1BB	0.9700
C3—C4	1.3570 (15)	C2B—C3B	1.3902 (16)
C4—C5	1.4316 (17)	C2B—C7B	1.3954 (16)
C4—H4A	0.9300	C3B—C4B	1.3927 (16)
C5—C6	1.3518 (19)	C3B—H3BA	0.9300
C5—H5A	0.9300	C4B—C5B	1.3922 (17)
C6—H6A	0.9300	C4B—H4BA	0.9300
C1A—C2A	1.5046 (15)	C5B—C6B	1.3886 (18)
C1A—H1AA	0.9700	C5B—H5BA	0.9300
C1A—H1AB	0.9700	C6B—C7B	1.3920 (16)
C2A—C3A	1.3925 (15)	C6B—H6BA	0.9300
C2A—C7A	1.3937 (16)	C7B—H7BA	0.9300
C1—S1A—C1A	99.49 (5)	C5A—C4A—C3A	119.75 (11)
C1—S1B—C1B	105.31 (5)	C5A—C4A—H4AA	120.1
C6—O2—C3	106.42 (9)	C3A—C4A—H4AA	120.1
C1—N1—N2	114.05 (9)	C6A—C5A—C4A	119.89 (10)
C2—N2—N1	121.44 (9)	C6A—C5A—H5AA	120.1
C2—N2—H2A	119.3	C4A—C5A—H5AA	120.1
N1—N2—H2A	119.3	C5A—C6A—C7A	120.21 (11)
N1—C1—S1A	120.42 (8)	C5A—C6A—H6AA	119.9
N1—C1—S1B	122.38 (8)	C7A—C6A—H6AA	119.9
S1A—C1—S1B	117.20 (6)	C6A—C7A—C2A	120.43 (11)
O1—C2—N2	125.12 (10)	C6A—C7A—H7AA	119.8
O1—C2—C3	122.36 (10)	C2A—C7A—H7AA	119.8
N2—C2—C3	112.51 (9)	C2B—C1B—S1B	104.83 (7)
C4—C3—O2	110.42 (10)	C2B—C1B—H1BA	110.8
C4—C3—C2	132.44 (10)	S1B—C1B—H1BA	110.8
O2—C3—C2	117.14 (9)	C2B—C1B—H1BB	110.8
C3—C4—C5	105.83 (11)	S1B—C1B—H1BB	110.8
C3—C4—H4A	127.1	H1BA—C1B—H1BB	108.9
C5—C4—H4A	127.1	C3B—C2B—C7B	119.53 (10)
C6—C5—C4	107.05 (10)	C3B—C2B—C1B	120.15 (10)
C6—C5—H5A	126.5	C7B—C2B—C1B	120.27 (10)
C4—C5—H5A	126.5	C2B—C3B—C4B	120.07 (11)
C5—C6—O2	110.29 (11)	C2B—C3B—H3BA	120.0
C5—C6—H6A	124.9	C4B—C3B—H3BA	120.0
O2—C6—H6A	124.9	C5B—C4B—C3B	120.34 (11)
C2A—C1A—S1A	109.68 (7)	C5B—C4B—H4BA	119.8
C2A—C1A—H1AA	109.7	C3B—C4B—H4BA	119.8
S1A—C1A—H1AA	109.7	C6B—C5B—C4B	119.65 (11)
C2A—C1A—H1AB	109.7	C6B—C5B—H5BA	120.2
S1A—C1A—H1AB	109.7	C4B—C5B—H5BA	120.2
H1AA—C1A—H1AB	108.2	C5B—C6B—C7B	120.12 (11)
C3A—C2A—C7A	118.85 (10)	C5B—C6B—H6BA	119.9
C3A—C2A—C1A	119.96 (10)	C7B—C6B—H6BA	119.9
C7A—C2A—C1A	121.18 (10)	C6B—C7B—C2B	120.28 (11)
C2A—C3A—C4A	120.83 (10)	C6B—C7B—H7BA	119.9
C2A—C3A—H3AA	119.6	C2B—C7B—H7BA	119.9
C4A—C3A—H3AA	119.6
C1—N1—N2—C2	166.99 (10)	S1A—C1A—C2A—C3A	113.50 (10)
N2—N1—C1—S1A	175.81 (8)	S1A—C1A—C2A—C7A	−67.69 (12)
N2—N1—C1—S1B	−4.57 (14)	C7A—C2A—C3A—C4A	−1.93 (16)
C1A—S1A—C1—N1	−2.02 (11)	C1A—C2A—C3A—C4A	176.90 (10)
C1A—S1A—C1—S1B	178.35 (7)	C2A—C3A—C4A—C5A	1.86 (17)
C1B—S1B—C1—N1	173.39 (10)	C3A—C4A—C5A—C6A	−0.14 (18)
C1B—S1B—C1—S1A	−6.99 (8)	C4A—C5A—C6A—C7A	−1.47 (18)
N1—N2—C2—O1	−1.29 (18)	C5A—C6A—C7A—C2A	1.39 (18)
N1—N2—C2—C3	179.69 (10)	C3A—C2A—C7A—C6A	0.31 (16)
C6—O2—C3—C4	−0.17 (13)	C1A—C2A—C7A—C6A	−178.51 (10)
C6—O2—C3—C2	178.91 (10)	C1—S1B—C1B—C2B	174.10 (8)
O1—C2—C3—C4	10.0 (2)	S1B—C1B—C2B—C3B	−94.13 (11)
N2—C2—C3—C4	−170.94 (12)	S1B—C1B—C2B—C7B	83.28 (11)
O1—C2—C3—O2	−168.84 (11)	C7B—C2B—C3B—C4B	−0.35 (16)
N2—C2—C3—O2	10.22 (14)	C1B—C2B—C3B—C4B	177.07 (10)
O2—C3—C4—C5	−0.02 (13)	C2B—C3B—C4B—C5B	0.23 (17)
C2—C3—C4—C5	−178.92 (12)	C3B—C4B—C5B—C6B	0.09 (17)
C3—C4—C5—C6	0.21 (14)	C4B—C5B—C6B—C7B	−0.28 (17)
C4—C5—C6—O2	−0.33 (15)	C5B—C6B—C7B—C2B	0.15 (17)
C3—O2—C6—C5	0.32 (14)	C3B—C2B—C7B—C6B	0.17 (16)
C1—S1A—C1A—C2A	−171.49 (8)	C1B—C2B—C7B—C6B	−177.26 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.22	2.6310 (12)	109
N2—H2A···S1B	0.86	2.37	2.8132 (10)	113
C4—H4A···O1^i	0.93	2.48	3.3823 (15)	164
C4A—H4AA···O1^ii	0.93	2.51	3.3136 (15)	145
C5B—H5BA···Cg1^iii	0.95	2.81	3.4504 (14)	127

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