Tetra-ethyl-ammonium 7,12-di-cyano-1-carba-closo-dodeca-borate.

In the title compound, C8H20N(+)·C3H10B11N2 (-), the carborane anion cage displays nearly-perfect Cs symmetry, with the two CN groups lying on a noncrystallographic mirror plane that bis-ects the cage. In the crystal, the anions form extended chains along the a-axis direction, with C-H⋯N hydrogen bonds linking consecutive anions. The C N bond lengths (and B-C N angles) in the nitrile moities are 1.1201 (19) Å, 178.60 (15)° and 1.1433 (17) Å, 179.45 (15)°, similar to those observed in organic nitriles. A hydrogen bond between a methylene H atom of the cation and the N atom in one of the nitrile groups of the anion is the closest contact between the anion and cation, at 2.52 Å.

Related literature

For the synthesis, and spectroscopic studies of the title compound and the related monosubstituted cyano compound, see: Rosenbaum et al. (2013 ▶). For gas phase acidity calculations of cyanated 1-carba-closo-dodeca­borate(1−) derivatives, see: Lipping et al. (2009 ▶). For studies of 1-carba-closo-dodeca­borate(1−) as a weakly coordinating anion, see: Reed (1998 ▶). For the title compound acting as a conjugate base for the strongest Brønsted acids, see: Juhasz et al. (2004 ▶). For a general review of the chemistry of the 1-carba-closo-dodeca­borate(1−) anion, see: Douvris & Michl (2013 ▶). For bond lengths of cyano groups in organic nitriles, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H20N+·C3H10B11N2 −

M = 323.45

Monoclinic,

a = 8.9280 (2) Å

b = 10.5695 (3) Å

c = 21.0620 (5) Å

β = 92.165 (2)°

V = 1986.09 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.40 mm−1

T = 100 K

0.72 × 0.11 × 0.09 mm

Data collection

Agilent Xcalibur (Onyx, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.874, T max = 1.000

13665 measured reflections

3549 independent reflections

3110 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.04

3549 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: OLEX2 (Dolomanov et al., 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814004759/lr2122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004759/lr2122Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004759/lr2122Isup3.cdx

CCDC reference: 989485

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

C8H20N+·C3H10B11N2−	F(000) = 688
Mr = 323.45	Dx = 1.081 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 8.9280 (2) Å	Cell parameters from 9624 reflections
b = 10.5695 (3) Å	θ = 4.2–67.0°
c = 21.0620 (5) Å	µ = 0.40 mm−1
β = 92.165 (2)°	T = 100 K
V = 1986.09 (8) Å3	Needle, clear light colourless
Z = 4	0.72 × 0.11 × 0.09 mm

Agilent Xcalibur (Onyx, Nova) diffractometer	3549 independent reflections
Radiation source: Nova (Cu) X-ray Source	3110 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
Detector resolution: 8.3552 pixels mm-1	θmax = 67.1°, θmin = 4.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
Tmin = 0.874, Tmax = 1.000	l = −25→18
13665 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Primary atom site location: iterative
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0746P)2 + 0.5426P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3549 reflections	Δρmax = 0.20 e Å−3
234 parameters	Δρmin = −0.21 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
N17	1.01231 (11)	0.69866 (9)	0.37094 (5)	0.0192 (2)
N14	0.76135 (13)	0.55607 (11)	0.51262 (5)	0.0293 (3)
C13	0.69013 (14)	0.61804 (12)	0.54418 (6)	0.0232 (3)
C1	0.32003 (14)	0.76849 (12)	0.62912 (6)	0.0226 (3)
H1	0.213 (2)	0.7535 (17)	0.6265 (9)	0.044 (5)*
C20	0.88278 (13)	0.77399 (12)	0.34123 (6)	0.0234 (3)
H20A	0.9091	0.8630	0.3426	0.028*
H20B	0.8704	0.7500	0.2969	0.028*
C18	1.03464 (14)	0.72809 (12)	0.44147 (6)	0.0231 (3)
H18A	0.9447	0.7038	0.4628	0.028*
H18B	1.1163	0.6764	0.4587	0.028*
C22	0.98194 (14)	0.55670 (11)	0.36737 (6)	0.0218 (3)
H22A	1.0667	0.5128	0.3873	0.026*
H22B	0.8950	0.5383	0.3920	0.026*
C25	1.29534 (14)	0.67411 (13)	0.35946 (6)	0.0255 (3)
H25A	1.3179	0.7028	0.4020	0.038*
H25B	1.3752	0.6977	0.3326	0.038*
H25C	1.2847	0.5837	0.3594	0.038*
C24	1.15065 (13)	0.73406 (12)	0.33489 (6)	0.0227 (3)
H24A	1.1340	0.7102	0.2907	0.027*
H24B	1.1623	0.8253	0.3363	0.027*
C23	0.95487 (15)	0.50319 (13)	0.30122 (7)	0.0303 (3)
H23A	0.8654	0.5397	0.2823	0.045*
H23B	0.9434	0.4130	0.3037	0.045*
H23C	1.0386	0.5229	0.2757	0.045*
C21	0.73378 (14)	0.75717 (13)	0.37238 (7)	0.0270 (3)
H21A	0.7071	0.6692	0.3722	0.041*
H21B	0.6579	0.8046	0.3493	0.041*
H21C	0.7420	0.7870	0.4154	0.041*
C15	0.84647 (15)	0.84551 (13)	0.64203 (6)	0.0276 (3)
N16	0.97050 (14)	0.86121 (14)	0.64645 (7)	0.0423 (3)
B11	0.59691 (15)	0.68338 (13)	0.67214 (6)	0.0214 (3)
H11	0.6671	0.6123	0.6971	0.026*
C19	1.06859 (17)	0.86511 (14)	0.45676 (7)	0.0336 (3)
H19A	1.1611	0.8889	0.4383	0.050*
H19B	1.0772	0.8759	0.5020	0.050*
H19C	0.9890	0.9175	0.4397	0.050*
B3	0.41460 (15)	0.75312 (14)	0.56090 (6)	0.0222 (3)
H3	0.3644	0.7261	0.5144	0.027*
B5	0.38243 (15)	0.88617 (14)	0.67872 (7)	0.0226 (3)
H5	0.3109	0.9451	0.7081	0.027*
B2	0.43587 (16)	0.64087 (14)	0.62446 (7)	0.0223 (3)
H2	0.3995	0.5419	0.6187	0.027*
B4	0.38189 (15)	0.90407 (14)	0.59491 (7)	0.0225 (3)
H4	0.3100	0.9745	0.5703	0.027*
B8	0.56256 (15)	0.86592 (13)	0.56845 (7)	0.0216 (3)
H8	0.6105	0.9117	0.5269	0.026*
B10	0.56283 (15)	0.83638 (14)	0.70569 (6)	0.0218 (3)
H10	0.6108	0.8638	0.7526	0.026*
B9	0.54205 (15)	0.94840 (13)	0.64211 (7)	0.0217 (3)
H9	0.5768	1.0477	0.6479	0.026*
B6	0.41595 (16)	0.72351 (14)	0.69686 (7)	0.0233 (3)
H6	0.3661	0.6776	0.7379	0.028*
B7	0.59456 (15)	0.70269 (13)	0.58752 (6)	0.0204 (3)
B12	0.67289 (15)	0.82232 (13)	0.63756 (6)	0.0205 (3)

	U11	U22	U33	U12	U13	U23
N17	0.0172 (5)	0.0209 (5)	0.0194 (5)	−0.0007 (4)	−0.0004 (4)	0.0010 (4)
N14	0.0295 (6)	0.0313 (6)	0.0273 (6)	0.0027 (5)	0.0039 (5)	0.0012 (5)
C13	0.0208 (6)	0.0265 (6)	0.0222 (6)	0.0004 (5)	0.0000 (5)	0.0045 (5)
C1	0.0163 (6)	0.0268 (6)	0.0246 (6)	−0.0010 (5)	0.0004 (5)	−0.0015 (5)
C20	0.0203 (6)	0.0233 (6)	0.0262 (6)	0.0016 (5)	−0.0039 (5)	0.0021 (5)
C18	0.0215 (6)	0.0292 (7)	0.0184 (6)	0.0014 (5)	−0.0010 (5)	−0.0019 (5)
C22	0.0201 (6)	0.0190 (6)	0.0262 (6)	−0.0008 (5)	0.0000 (5)	0.0011 (5)
C25	0.0209 (6)	0.0310 (7)	0.0248 (6)	0.0014 (5)	0.0039 (5)	0.0025 (5)
C24	0.0211 (6)	0.0248 (6)	0.0224 (6)	−0.0030 (5)	0.0028 (5)	0.0038 (5)
C23	0.0316 (7)	0.0279 (7)	0.0309 (7)	−0.0007 (6)	−0.0042 (5)	−0.0054 (5)
C21	0.0198 (6)	0.0277 (7)	0.0333 (7)	0.0025 (5)	−0.0025 (5)	−0.0011 (5)
C15	0.0244 (7)	0.0306 (7)	0.0279 (7)	0.0012 (5)	0.0005 (5)	−0.0014 (5)
N16	0.0238 (7)	0.0541 (9)	0.0492 (8)	0.0000 (6)	0.0020 (5)	−0.0046 (6)
B11	0.0219 (7)	0.0233 (7)	0.0189 (6)	0.0017 (5)	0.0010 (5)	0.0013 (5)
C19	0.0356 (7)	0.0302 (7)	0.0346 (8)	0.0052 (6)	−0.0069 (6)	−0.0099 (6)
B3	0.0195 (7)	0.0269 (7)	0.0200 (7)	0.0006 (5)	−0.0009 (5)	−0.0004 (5)
B5	0.0183 (6)	0.0263 (7)	0.0233 (7)	0.0003 (5)	0.0014 (5)	−0.0016 (6)
B2	0.0215 (7)	0.0235 (7)	0.0219 (7)	−0.0017 (5)	0.0020 (5)	−0.0002 (5)
B4	0.0188 (6)	0.0242 (7)	0.0244 (7)	0.0010 (5)	−0.0010 (5)	0.0008 (6)
B8	0.0192 (6)	0.0241 (7)	0.0216 (7)	0.0005 (5)	0.0004 (5)	0.0028 (5)
B10	0.0189 (6)	0.0264 (7)	0.0199 (6)	0.0014 (5)	−0.0006 (5)	−0.0014 (5)
B9	0.0177 (6)	0.0226 (7)	0.0246 (7)	0.0000 (5)	0.0000 (5)	−0.0004 (5)
B6	0.0226 (7)	0.0266 (7)	0.0209 (7)	−0.0011 (6)	0.0034 (5)	0.0008 (5)
B7	0.0195 (6)	0.0228 (7)	0.0189 (6)	0.0008 (5)	0.0013 (5)	0.0008 (5)
B12	0.0158 (6)	0.0231 (7)	0.0226 (7)	−0.0001 (5)	0.0004 (5)	−0.0003 (5)

N17—C20	1.5192 (15)	B11—B2	1.780 (2)
N17—C24	1.5208 (15)	B11—B12	1.785 (2)
N17—C18	1.5234 (15)	B11—B7	1.7932 (19)
N17—C22	1.5261 (15)	B11—B10	1.795 (2)
N14—C13	1.1433 (17)	B11—H11	1.1000
C13—B7	1.5558 (18)	C19—H19A	0.9600
C1—B3	1.7016 (18)	C19—H19B	0.9600
C1—B6	1.7037 (19)	C19—H19C	0.9600
C1—B5	1.7043 (18)	B3—B7	1.7640 (19)
C1—B2	1.7048 (19)	B3—B4	1.778 (2)
C1—B4	1.7052 (19)	B3—B8	1.7821 (19)
C1—H1	0.965 (19)	B3—B2	1.793 (2)
C20—C21	1.5158 (18)	B3—H3	1.1000
C20—H20A	0.9700	B5—B10	1.7676 (19)
C20—H20B	0.9700	B5—B9	1.7723 (19)
C18—C19	1.5117 (19)	B5—B4	1.7751 (19)
C18—H18A	0.9700	B5—B6	1.784 (2)
C18—H18B	0.9700	B5—H5	1.1000
C22—C23	1.5146 (18)	B2—B7	1.7672 (19)
C22—H22A	0.9700	B2—B6	1.7721 (19)
C22—H22B	0.9700	B2—H2	1.1000
C25—C24	1.5125 (17)	B4—B8	1.7728 (19)
C25—H25A	0.9600	B4—B9	1.7734 (19)
C25—H25B	0.9600	B4—H4	1.1000
C25—H25C	0.9600	B8—B12	1.7869 (19)
C24—H24A	0.9700	B8—B7	1.7919 (19)
C24—H24B	0.9700	B8—B9	1.7950 (19)
C23—H23A	0.9600	B8—H8	1.1000
C23—H23B	0.9600	B10—B12	1.7757 (18)
C23—H23C	0.9600	B10—B6	1.777 (2)
C21—H21A	0.9600	B10—B9	1.7918 (19)
C21—H21B	0.9600	B10—H10	1.1000
C21—H21C	0.9600	B9—B12	1.7771 (19)
C15—N16	1.1201 (19)	B9—H9	1.1000
C15—B12	1.5683 (18)	B6—H6	1.1000
B11—B6	1.7677 (19)	B7—B12	1.7727 (19)
C20—N17—C24	106.58 (9)	B7—B2—B6	107.74 (10)
C20—N17—C18	111.36 (9)	C1—B2—B11	104.28 (10)
C24—N17—C18	110.96 (9)	B7—B2—B11	60.73 (8)
C20—N17—C22	111.34 (9)	B6—B2—B11	59.69 (8)
C24—N17—C22	111.31 (9)	C1—B2—B3	58.14 (8)
C18—N17—C22	105.38 (9)	B7—B2—B3	59.39 (8)
N14—C13—B7	179.45 (15)	B6—B2—B3	107.75 (10)
B3—C1—B6	115.51 (10)	B11—B2—B3	108.34 (10)
B3—C1—B5	115.22 (10)	C1—B2—H2	125.5
B6—C1—B5	63.13 (8)	B7—B2—H2	122.8
B3—C1—B2	63.54 (8)	B6—B2—H2	121.6
B6—C1—B2	62.65 (8)	B11—B2—H2	122.0
B5—C1—B2	115.33 (10)	B3—B2—H2	121.6
B3—C1—B4	62.90 (8)	C1—B4—B8	104.76 (10)
B6—C1—B4	115.32 (10)	C1—B4—B9	104.62 (10)
B5—C1—B4	62.75 (8)	B8—B4—B9	60.82 (8)
B2—C1—B4	115.70 (10)	C1—B4—B5	58.60 (8)
B3—C1—H1	117.1 (11)	B8—B4—B5	108.67 (10)
B6—C1—H1	117.8 (11)	B9—B4—B5	59.93 (8)
B5—C1—H1	117.0 (11)	C1—B4—B3	58.45 (8)
B2—C1—H1	117.8 (11)	B8—B4—B3	60.26 (8)
B4—C1—H1	116.7 (11)	B9—B4—B3	108.77 (10)
C21—C20—N17	115.28 (10)	B5—B4—B3	108.10 (10)
C21—C20—H20A	108.5	C1—B4—H4	125.1
N17—C20—H20A	108.5	B8—B4—H4	121.8
C21—C20—H20B	108.5	B9—B4—H4	122.0
N17—C20—H20B	108.5	B5—B4—H4	121.4
H20A—C20—H20B	107.5	B3—B4—H4	121.3
C19—C18—N17	114.90 (11)	B4—B8—B3	60.00 (8)
C19—C18—H18A	108.5	B4—B8—B12	106.42 (9)
N17—C18—H18A	108.5	B3—B8—B12	106.50 (10)
C19—C18—H18B	108.5	B4—B8—B7	106.72 (10)
N17—C18—H18B	108.5	B3—B8—B7	59.15 (8)
H18A—C18—H18B	107.5	B12—B8—B7	59.38 (8)
C23—C22—N17	115.74 (10)	B4—B8—B9	59.61 (8)
C23—C22—H22A	108.3	B3—B8—B9	107.61 (9)
N17—C22—H22A	108.3	B12—B8—B9	59.49 (8)
C23—C22—H22B	108.3	B7—B8—B9	107.12 (9)
N17—C22—H22B	108.3	B4—B8—H8	122.4
H22A—C22—H22B	107.4	B3—B8—H8	122.2
C24—C25—H25A	109.5	B12—B8—H8	122.8
C24—C25—H25B	109.5	B7—B8—H8	122.5
H25A—C25—H25B	109.5	B9—B8—H8	121.9
C24—C25—H25C	109.5	B5—B10—B12	106.89 (9)
H25A—C25—H25C	109.5	B5—B10—B6	60.43 (8)
H25B—C25—H25C	109.5	B12—B10—B6	106.73 (10)
C25—C24—N17	115.18 (10)	B5—B10—B9	59.72 (8)
C25—C24—H24A	108.5	B12—B10—B9	59.75 (8)
N17—C24—H24A	108.5	B6—B10—B9	108.07 (9)
C25—C24—H24B	108.5	B5—B10—B11	107.92 (10)
N17—C24—H24B	108.5	B12—B10—B11	59.96 (8)
H24A—C24—H24B	107.5	B6—B10—B11	59.31 (8)
C22—C23—H23A	109.5	B9—B10—B11	108.38 (9)
C22—C23—H23B	109.5	B5—B10—H10	121.9
H23A—C23—H23B	109.5	B12—B10—H10	122.6
C22—C23—H23C	109.5	B6—B10—H10	122.1
H23A—C23—H23C	109.5	B9—B10—H10	121.5
H23B—C23—H23C	109.5	B11—B10—H10	121.6
C20—C21—H21A	109.5	B5—B9—B4	60.08 (8)
C20—C21—H21B	109.5	B5—B9—B12	106.63 (10)
H21A—C21—H21B	109.5	B4—B9—B12	106.82 (10)
C20—C21—H21C	109.5	B5—B9—B10	59.46 (8)
H21A—C21—H21C	109.5	B4—B9—B10	107.63 (10)
H21B—C21—H21C	109.5	B12—B9—B10	59.68 (7)
N16—C15—B12	178.60 (15)	B5—B9—B8	107.81 (10)
B6—B11—B2	59.93 (8)	B4—B9—B8	59.58 (8)
B6—B11—B12	106.76 (10)	B12—B9—B8	60.03 (8)
B2—B11—B12	106.79 (9)	B10—B9—B8	108.30 (10)
B6—B11—B7	106.79 (10)	B5—B9—H9	122.2
B2—B11—B7	59.28 (7)	B4—B9—H9	122.2
B12—B11—B7	59.40 (8)	B12—B9—H9	122.6
B6—B11—B10	59.84 (8)	B10—B9—H9	121.7
B2—B11—B10	107.70 (10)	B8—B9—H9	121.5
B12—B11—B10	59.47 (8)	C1—B6—B11	104.86 (9)
B7—B11—B10	107.02 (10)	C1—B6—B2	58.71 (8)
B6—B11—H11	122.3	B11—B6—B2	60.38 (8)
B2—B11—H11	122.1	C1—B6—B10	104.23 (10)
B12—B11—H11	122.6	B11—B6—B10	60.85 (8)
B7—B11—H11	122.6	B2—B6—B10	108.86 (10)
B10—B11—H11	121.9	C1—B6—B5	58.45 (8)
C18—C19—H19A	109.5	B11—B6—B5	108.42 (10)
C18—C19—H19B	109.5	B2—B6—B5	108.20 (10)
H19A—C19—H19B	109.5	B10—B6—B5	59.52 (8)
C18—C19—H19C	109.5	C1—B6—H6	125.2
H19A—C19—H19C	109.5	B11—B6—H6	121.8
H19B—C19—H19C	109.5	B2—B6—H6	121.0
C1—B3—B7	103.62 (9)	B10—B6—H6	122.2
C1—B3—B4	58.65 (8)	B5—B6—H6	121.6
B7—B3—B4	107.74 (10)	C13—B7—B3	120.02 (10)
C1—B3—B8	104.51 (10)	C13—B7—B2	120.81 (11)
B7—B3—B8	60.70 (8)	B3—B7—B2	61.05 (8)
B4—B3—B8	59.74 (8)	C13—B7—B12	123.11 (11)
C1—B3—B2	58.32 (8)	B3—B7—B12	107.91 (10)
B7—B3—B2	59.56 (8)	B2—B7—B12	107.87 (10)
B4—B3—B2	107.90 (10)	C13—B7—B8	120.56 (10)
B8—B3—B2	108.59 (9)	B3—B7—B8	60.15 (8)
C1—B3—H3	125.4	B2—B7—B8	109.33 (10)
B7—B3—H3	122.7	B12—B7—B8	60.17 (8)
B4—B3—H3	121.6	C13—B7—B11	122.11 (11)
B8—B3—H3	121.9	B3—B7—B11	109.06 (9)
B2—B3—H3	121.5	B2—B7—B11	59.99 (8)
C1—B5—B10	104.62 (10)	B12—B7—B11	60.05 (8)
C1—B5—B9	104.70 (9)	B8—B7—B11	109.16 (10)
B10—B5—B9	60.82 (8)	C15—B12—B7	120.93 (11)
C1—B5—B4	58.65 (8)	C15—B12—B10	120.93 (11)
B10—B5—B4	108.63 (10)	B7—B12—B10	108.80 (10)
B9—B5—B4	59.99 (8)	C15—B12—B9	121.98 (11)
C1—B5—B6	58.42 (8)	B7—B12—B9	108.76 (9)
B10—B5—B6	60.06 (8)	B10—B12—B9	60.57 (8)
B9—B5—B6	108.64 (10)	C15—B12—B11	119.61 (11)
B4—B5—B6	108.05 (10)	B7—B12—B11	60.54 (8)
C1—B5—H5	125.1	B10—B12—B11	60.57 (8)
B10—B5—H5	121.9	B9—B12—B11	109.53 (9)
B9—B5—H5	121.9	C15—B12—B8	121.44 (11)
B4—B5—H5	121.3	B7—B12—B8	60.45 (8)
B6—B5—H5	121.4	B10—B12—B8	109.38 (9)
C1—B2—B7	103.35 (10)	B9—B12—B8	60.48 (8)
C1—B2—B6	58.64 (8)	B11—B12—B8	109.78 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N16i	0.968 (18)	2.496 (18)	3.3042 (18)	140.9 (14)
C18—H18a···N14	0.97	2.52	3.4323 (17)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N16i	0.968 (18)	2.496 (18)	3.3042 (18)	140.9 (14)
C18—H18a⋯N14	0.97	2.52	3.4323 (17)	157

Symmetry code: (i) .