4-Carbamoylpiperidinium 2-carb-oxy-benzoate-benzene-1,2-dicarb-oxy-lic acid (1/1).

The asymmetric unit of the title salt adduct, C(6)H(13)N(2)O(+)·C(8)H(5)O(4) (-)·C(8)H(6)O(4), comprises one isonipecotamide cation, a hydrogen phthalate anion and a phthalic acid adduct mol-ecule. These form a two-dimensional hydrogen-bonded network through head-to-tail cation-anion-adduct mol-ecule inter-actions which include a cyclic heteromolecular amide-carboxyl-ate motif [graph set R(2) (2)(8)], conjoint cyclic R(2) (2)(6) and R(3) (3)(10) piperidinium N-H⋯O(carbox-yl) associations, as well as strong carboxyl O-H⋯O(carbox-yl) hydrogen bonds.

Related literature

For structural data on isonipecotamide salts, see: Smith et al. (2010 ▶); Smith & Wermuth (2010a ▶,b ▶,c ▶,d ▶, 2011 ▶). For the crystal structure of o-phthalic acid, see: Ermer (1981 ▶). For hydrogen-bonding graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H13N2O+·C8H5O4 −·C8H6O4

M = 460.43

Triclinic,

a = 8.7857 (4) Å

b = 11.7907 (6) Å

c = 12.3188 (6) Å

α = 62.496 (5)°

β = 85.916 (4)°

γ = 82.604 (4)°

V = 1122.36 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.40 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.923, T max = 0.980

13586 measured reflections

4401 independent reflections

3444 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.07

4401 reflections

326 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003825/wn2419sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003825/wn2419Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H13N2O+·C8H5O4−·C8H6O4	Z = 2
Mr = 460.43	F(000) = 484
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7857 (4) Å	Cell parameters from 6939 reflections
b = 11.7907 (6) Å	θ = 3.2–28.7°
c = 12.3188 (6) Å	µ = 0.11 mm−1
α = 62.496 (5)°	T = 200 K
β = 85.916 (4)°	Plate, colourless
γ = 82.604 (4)°	0.40 × 0.30 × 0.18 mm
V = 1122.36 (11) Å3

Oxford Diffraction Gemini-S CCD-detector diffractometer	4401 independent reflections
Radiation source: Enhance (Mo) X-ray source	3444 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.923, Tmax = 0.980	l = −15→15
13586 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0531P)2] where P = (Fo2 + 2Fc2)/3
4401 reflections	(Δ/σ)max = 0.001
326 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O41C	0.74423 (12)	0.61632 (11)	−0.02736 (9)	0.0416 (3)
N1C	1.00683 (14)	0.42772 (13)	0.35653 (11)	0.0325 (4)
N41C	0.52124 (15)	0.58014 (14)	0.08017 (12)	0.0383 (4)
C2C	0.85240 (17)	0.48482 (14)	0.37702 (12)	0.0316 (5)
C3C	0.77366 (16)	0.56671 (13)	0.25569 (12)	0.0279 (4)
C4C	0.75894 (15)	0.48525 (13)	0.19015 (12)	0.0255 (4)
C5C	0.91666 (17)	0.42485 (15)	0.17252 (13)	0.0352 (5)
C6C	0.99655 (17)	0.34593 (15)	0.29489 (13)	0.0355 (5)
C41C	0.67380 (16)	0.56532 (14)	0.07155 (12)	0.0287 (4)
O11A	0.80799 (12)	0.85845 (10)	0.30180 (10)	0.0382 (3)
O12A	1.01504 (12)	0.71996 (11)	0.38418 (9)	0.0457 (4)
O21A	1.15402 (13)	0.64611 (10)	0.19609 (10)	0.0428 (4)
O22A	1.34884 (12)	0.66738 (10)	0.28975 (10)	0.0350 (3)
C1A	1.04746 (16)	0.90657 (13)	0.19787 (11)	0.0257 (4)
C2A	1.18683 (15)	0.85461 (13)	0.16830 (12)	0.0273 (4)
C3A	1.28238 (18)	0.93696 (15)	0.07974 (14)	0.0388 (5)
C4A	1.2394 (2)	1.06857 (16)	0.02235 (15)	0.0456 (5)
C5A	1.10150 (19)	1.11900 (15)	0.05043 (14)	0.0402 (5)
C6A	1.00445 (17)	1.03847 (13)	0.13774 (12)	0.0321 (4)
C11A	0.95520 (16)	0.81938 (13)	0.30320 (12)	0.0270 (4)
C21A	1.22700 (16)	0.71181 (14)	0.22139 (12)	0.0285 (4)
O11B	0.55460 (12)	0.56551 (9)	0.65124 (9)	0.0375 (3)
O12B	0.70819 (11)	0.67951 (10)	0.49932 (9)	0.0365 (3)
O21B	0.62518 (11)	0.72888 (11)	0.75928 (9)	0.0380 (3)
O22B	0.39403 (12)	0.75761 (11)	0.83676 (9)	0.0443 (4)
C1B	0.47554 (15)	0.78671 (12)	0.53468 (12)	0.0234 (4)
C2B	0.41733 (15)	0.82601 (12)	0.62266 (12)	0.0250 (4)
C3B	0.30225 (17)	0.92762 (14)	0.59082 (14)	0.0332 (5)
C4B	0.24536 (18)	0.99166 (14)	0.47329 (15)	0.0400 (5)
C5B	0.30399 (18)	0.95471 (14)	0.38598 (14)	0.0380 (5)
C6B	0.41770 (17)	0.85304 (13)	0.41663 (13)	0.0309 (4)
C11B	0.58924 (15)	0.66926 (13)	0.56461 (12)	0.0251 (4)
C21B	0.47720 (16)	0.76662 (13)	0.75001 (12)	0.0282 (4)
H4C	0.69780	0.41540	0.24300	0.0310*
H11C	1.068 (2)	0.4933 (17)	0.3102 (16)	0.051 (5)*
H12C	1.0542 (19)	0.3761 (16)	0.4339 (16)	0.048 (5)*
H21C	0.86350	0.53720	0.41730	0.0380*
H22C	0.79060	0.41670	0.42960	0.0380*
H31C	0.83260	0.63760	0.20490	0.0330*
H32C	0.67250	0.60230	0.26930	0.0330*
H41C	0.461 (2)	0.6370 (17)	0.0071 (17)	0.058 (5)*
H42C	0.475 (2)	0.5356 (17)	0.1562 (17)	0.054 (5)*
H51C	0.90570	0.36990	0.13500	0.0420*
H52C	0.97860	0.49200	0.11810	0.0420*
H61C	0.93950	0.27400	0.34670	0.0430*
H62C	1.09880	0.31190	0.28190	0.0430*
H3A	1.37520	0.90370	0.05900	0.0470*
H4A	1.30450	1.12320	−0.03570	0.0550*
H5A	1.07320	1.20730	0.01080	0.0480*
H6A	0.91060	1.07260	0.15610	0.0380*
H11A	0.762 (2)	0.793 (2)	0.3786 (19)	0.078 (6)*
H22A	1.374 (2)	0.583 (2)	0.3154 (18)	0.072 (6)*
H3B	0.26280	0.95300	0.64920	0.0400*
H4B	0.16780	1.05940	0.45310	0.0480*
H5B	0.26690	0.99830	0.30660	0.0460*
H6B	0.45630	0.82850	0.35750	0.0370*
H21B	0.664 (2)	0.691 (2)	0.844 (2)	0.081 (7)*

	U11	U22	U33	U12	U13	U23
O41C	0.0306 (6)	0.0590 (7)	0.0233 (5)	−0.0098 (5)	0.0002 (4)	−0.0077 (5)
N1C	0.0310 (7)	0.0316 (7)	0.0255 (6)	−0.0079 (6)	−0.0069 (6)	−0.0032 (6)
N41C	0.0285 (7)	0.0545 (9)	0.0257 (7)	−0.0019 (6)	−0.0009 (6)	−0.0138 (7)
C2C	0.0382 (9)	0.0315 (8)	0.0255 (7)	−0.0033 (7)	−0.0024 (6)	−0.0133 (6)
C3C	0.0290 (8)	0.0272 (7)	0.0255 (7)	−0.0033 (6)	−0.0021 (6)	−0.0101 (6)
C4C	0.0256 (7)	0.0278 (7)	0.0216 (7)	−0.0058 (6)	0.0004 (5)	−0.0093 (6)
C5C	0.0340 (8)	0.0430 (9)	0.0282 (8)	0.0018 (7)	−0.0001 (6)	−0.0175 (7)
C6C	0.0301 (8)	0.0360 (9)	0.0356 (8)	0.0038 (7)	−0.0007 (6)	−0.0141 (7)
C41C	0.0280 (8)	0.0351 (8)	0.0256 (7)	−0.0061 (6)	−0.0006 (6)	−0.0155 (6)
O11A	0.0307 (6)	0.0306 (6)	0.0376 (6)	0.0049 (5)	0.0092 (5)	−0.0057 (5)
O12A	0.0312 (6)	0.0454 (7)	0.0307 (6)	0.0011 (5)	0.0005 (5)	0.0063 (5)
O21A	0.0453 (7)	0.0335 (6)	0.0459 (6)	−0.0133 (5)	−0.0085 (5)	−0.0116 (5)
O22A	0.0294 (6)	0.0271 (6)	0.0485 (6)	0.0029 (5)	−0.0075 (5)	−0.0178 (5)
C1A	0.0279 (7)	0.0259 (7)	0.0211 (7)	−0.0046 (6)	−0.0022 (6)	−0.0083 (6)
C2A	0.0253 (7)	0.0283 (8)	0.0249 (7)	−0.0062 (6)	−0.0011 (6)	−0.0083 (6)
C3A	0.0290 (8)	0.0378 (9)	0.0386 (8)	−0.0059 (7)	0.0051 (7)	−0.0083 (7)
C4A	0.0402 (10)	0.0367 (9)	0.0403 (9)	−0.0137 (8)	0.0060 (7)	0.0005 (8)
C5A	0.0446 (10)	0.0242 (8)	0.0376 (8)	−0.0041 (7)	−0.0045 (7)	−0.0016 (7)
C6A	0.0342 (8)	0.0277 (8)	0.0289 (7)	0.0005 (7)	−0.0034 (6)	−0.0089 (6)
C11A	0.0287 (8)	0.0271 (8)	0.0237 (7)	−0.0024 (6)	−0.0004 (6)	−0.0106 (6)
C21A	0.0242 (7)	0.0302 (8)	0.0282 (7)	−0.0058 (6)	0.0049 (6)	−0.0110 (6)
O11B	0.0377 (6)	0.0231 (5)	0.0381 (6)	0.0013 (5)	0.0143 (5)	−0.0056 (5)
O12B	0.0278 (6)	0.0373 (6)	0.0324 (5)	0.0012 (5)	0.0100 (4)	−0.0083 (5)
O21B	0.0281 (6)	0.0522 (7)	0.0244 (5)	−0.0004 (5)	−0.0019 (4)	−0.0104 (5)
O22B	0.0407 (7)	0.0563 (8)	0.0295 (6)	0.0060 (6)	0.0030 (5)	−0.0175 (5)
C1B	0.0209 (7)	0.0206 (7)	0.0265 (7)	−0.0045 (6)	0.0001 (5)	−0.0085 (6)
C2B	0.0244 (7)	0.0214 (7)	0.0281 (7)	−0.0050 (6)	0.0007 (6)	−0.0099 (6)
C3B	0.0347 (8)	0.0274 (8)	0.0377 (8)	0.0014 (7)	0.0010 (7)	−0.0165 (7)
C4B	0.0372 (9)	0.0265 (8)	0.0493 (10)	0.0096 (7)	−0.0118 (7)	−0.0132 (7)
C5B	0.0420 (9)	0.0306 (8)	0.0355 (8)	0.0016 (7)	−0.0176 (7)	−0.0092 (7)
C6B	0.0345 (8)	0.0299 (8)	0.0292 (7)	−0.0024 (7)	−0.0057 (6)	−0.0139 (6)
C11B	0.0238 (7)	0.0266 (7)	0.0232 (7)	−0.0022 (6)	0.0017 (6)	−0.0103 (6)
C21B	0.0308 (8)	0.0245 (7)	0.0273 (7)	−0.0033 (6)	0.0017 (6)	−0.0103 (6)

O41C—C41C	1.2413 (17)	C5C—H51C	0.9700
O11A—C11A	1.3144 (18)	C5C—H52C	0.9700
O12A—C11A	1.2172 (19)	C6C—H61C	0.9700
O21A—C21A	1.220 (2)	C6C—H62C	0.9700
O22A—C21A	1.3062 (18)	C1A—C11A	1.4934 (19)
O11A—H11A	1.00 (2)	C1A—C2A	1.399 (2)
O22A—H22A	0.90 (2)	C1A—C6A	1.391 (2)
O11B—C11B	1.2537 (18)	C2A—C21A	1.500 (2)
O12B—C11B	1.2557 (17)	C2A—C3A	1.392 (2)
O21B—C21B	1.3140 (18)	C3A—C4A	1.387 (3)
O22B—C21B	1.2211 (17)	C4A—C5A	1.373 (3)
O21B—H21B	0.99 (2)	C5A—C6A	1.386 (2)
N1C—C6C	1.491 (2)	C3A—H3A	0.9300
N1C—C2C	1.494 (2)	C4A—H4A	0.9300
N41C—C41C	1.332 (2)	C5A—H5A	0.9300
N1C—H12C	0.953 (18)	C6A—H6A	0.9300
N1C—H11C	0.932 (19)	C1B—C2B	1.405 (2)
N41C—H42C	0.930 (18)	C1B—C11B	1.509 (2)
N41C—H41C	0.979 (19)	C1B—C6B	1.3918 (19)
C2C—C3C	1.5123 (19)	C2B—C3B	1.386 (2)
C3C—C4C	1.534 (2)	C2B—C21B	1.4954 (19)
C4C—C5C	1.523 (2)	C3B—C4B	1.383 (2)
C4C—C41C	1.5117 (19)	C4B—C5B	1.381 (2)
C5C—C6C	1.523 (2)	C5B—C6B	1.380 (2)
C2C—H21C	0.9700	C3B—H3B	0.9300
C2C—H22C	0.9700	C4B—H4B	0.9300
C3C—H31C	0.9700	C5B—H5B	0.9300
C3C—H32C	0.9700	C6B—H6B	0.9300
C4C—H4C	0.9800
C11A—O11A—H11A	106.6 (12)	C2A—C1A—C11A	118.40 (13)
C21A—O22A—H22A	112.4 (12)	C3A—C2A—C21A	119.76 (14)
C21B—O21B—H21B	113.9 (11)	C1A—C2A—C3A	119.05 (15)
C2C—N1C—C6C	112.01 (12)	C1A—C2A—C21A	120.92 (12)
H11C—N1C—H12C	107.8 (15)	C2A—C3A—C4A	120.14 (16)
C6C—N1C—H11C	110.2 (12)	C3A—C4A—C5A	120.62 (16)
C2C—N1C—H11C	109.5 (12)	C4A—C5A—C6A	120.06 (17)
C2C—N1C—H12C	108.5 (11)	C1A—C6A—C5A	119.96 (15)
C6C—N1C—H12C	108.8 (13)	O12A—C11A—C1A	121.18 (13)
H41C—N41C—H42C	121.8 (16)	O11A—C11A—O12A	123.45 (13)
C41C—N41C—H42C	118.5 (11)	O11A—C11A—C1A	115.38 (13)
C41C—N41C—H41C	119.7 (11)	O22A—C21A—C2A	114.51 (14)
N1C—C2C—C3C	109.73 (11)	O21A—C21A—C2A	121.23 (13)
C2C—C3C—C4C	110.03 (13)	O21A—C21A—O22A	124.16 (16)
C5C—C4C—C41C	113.04 (12)	C2A—C3A—H3A	120.00
C3C—C4C—C5C	110.14 (12)	C4A—C3A—H3A	120.00
C3C—C4C—C41C	110.15 (13)	C5A—C4A—H4A	120.00
C4C—C5C—C6C	110.52 (12)	C3A—C4A—H4A	120.00
N1C—C6C—C5C	110.09 (14)	C4A—C5A—H5A	120.00
O41C—C41C—C4C	120.98 (13)	C6A—C5A—H5A	120.00
N41C—C41C—C4C	116.38 (12)	C5A—C6A—H6A	120.00
O41C—C41C—N41C	122.62 (13)	C1A—C6A—H6A	120.00
N1C—C2C—H21C	110.00	C2B—C1B—C6B	118.78 (14)
H21C—C2C—H22C	108.00	C6B—C1B—C11B	118.11 (13)
C3C—C2C—H21C	110.00	C2B—C1B—C11B	122.94 (12)
C3C—C2C—H22C	110.00	C1B—C2B—C21B	123.27 (13)
N1C—C2C—H22C	110.00	C3B—C2B—C21B	117.17 (13)
C4C—C3C—H31C	110.00	C1B—C2B—C3B	119.52 (13)
C2C—C3C—H32C	110.00	C2B—C3B—C4B	120.84 (15)
H31C—C3C—H32C	108.00	C3B—C4B—C5B	119.83 (16)
C4C—C3C—H32C	110.00	C4B—C5B—C6B	119.96 (14)
C2C—C3C—H31C	110.00	C1B—C6B—C5B	121.06 (14)
C41C—C4C—H4C	108.00	O11B—C11B—C1B	116.96 (12)
C5C—C4C—H4C	108.00	O12B—C11B—C1B	118.86 (13)
C3C—C4C—H4C	108.00	O11B—C11B—O12B	124.11 (15)
C4C—C5C—H51C	110.00	O21B—C21B—C2B	114.59 (12)
C4C—C5C—H52C	110.00	O22B—C21B—C2B	121.76 (13)
C6C—C5C—H51C	110.00	O21B—C21B—O22B	123.64 (13)
C6C—C5C—H52C	110.00	C2B—C3B—H3B	120.00
H51C—C5C—H52C	108.00	C4B—C3B—H3B	120.00
C5C—C6C—H61C	110.00	C3B—C4B—H4B	120.00
H61C—C6C—H62C	108.00	C5B—C4B—H4B	120.00
C5C—C6C—H62C	110.00	C4B—C5B—H5B	120.00
N1C—C6C—H61C	110.00	C6B—C5B—H5B	120.00
N1C—C6C—H62C	110.00	C1B—C6B—H6B	119.00
C2A—C1A—C6A	120.16 (13)	C5B—C6B—H6B	119.00
C6A—C1A—C11A	121.15 (13)
C6C—N1C—C2C—C3C	−59.45 (17)	C1A—C2A—C21A—O22A	−117.75 (15)
C2C—N1C—C6C—C5C	58.30 (15)	C3A—C2A—C21A—O21A	−108.28 (17)
N1C—C2C—C3C—C4C	58.11 (16)	C3A—C2A—C21A—O22A	68.28 (18)
C2C—C3C—C4C—C5C	−57.23 (15)	C2A—C3A—C4A—C5A	−1.1 (3)
C2C—C3C—C4C—C41C	177.41 (11)	C3A—C4A—C5A—C6A	0.7 (3)
C3C—C4C—C5C—C6C	56.17 (17)	C4A—C5A—C6A—C1A	0.7 (2)
C41C—C4C—C5C—C6C	179.86 (14)	C6B—C1B—C2B—C3B	1.3 (2)
C3C—C4C—C41C—O41C	97.27 (18)	C6B—C1B—C2B—C21B	−176.43 (14)
C3C—C4C—C41C—N41C	−81.09 (18)	C11B—C1B—C2B—C3B	−173.80 (14)
C5C—C4C—C41C—O41C	−26.4 (2)	C11B—C1B—C2B—C21B	8.5 (2)
C5C—C4C—C41C—N41C	155.23 (16)	C2B—C1B—C6B—C5B	−0.8 (2)
C4C—C5C—C6C—N1C	−56.27 (17)	C11B—C1B—C6B—C5B	174.56 (14)
C6A—C1A—C2A—C3A	1.1 (2)	C2B—C1B—C11B—O11B	52.9 (2)
C6A—C1A—C2A—C21A	−172.89 (13)	C2B—C1B—C11B—O12B	−130.04 (15)
C11A—C1A—C2A—C3A	−172.71 (14)	C6B—C1B—C11B—O11B	−122.25 (15)
C11A—C1A—C2A—C21A	13.3 (2)	C6B—C1B—C11B—O12B	54.86 (19)
C2A—C1A—C6A—C5A	−1.6 (2)	C1B—C2B—C3B—C4B	−0.8 (2)
C11A—C1A—C6A—C5A	172.11 (14)	C21B—C2B—C3B—C4B	177.07 (14)
C2A—C1A—C11A—O11A	−157.57 (14)	C1B—C2B—C21B—O21B	34.0 (2)
C2A—C1A—C11A—O12A	23.0 (2)	C1B—C2B—C21B—O22B	−147.67 (16)
C6A—C1A—C11A—O11A	28.7 (2)	C3B—C2B—C21B—O21B	−143.76 (15)
C6A—C1A—C11A—O12A	−150.80 (15)	C3B—C2B—C21B—O22B	34.6 (2)
C1A—C2A—C3A—C4A	0.2 (2)	C2B—C3B—C4B—C5B	−0.3 (2)
C21A—C2A—C3A—C4A	174.29 (15)	C3B—C4B—C5B—C6B	0.8 (3)
C1A—C2A—C21A—O21A	65.69 (19)	C4B—C5B—C6B—C1B	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1C—H11C···O21A	0.932 (19)	1.911 (19)	2.8287 (18)	167.7 (16)
N1C—H12C···O12Ai	0.953 (18)	2.077 (17)	2.8519 (16)	137.4 (14)
N1C—H12C···O12Bi	0.953 (18)	2.204 (17)	2.9606 (16)	135.6 (14)
N41C—H41C···O22Bii	0.979 (19)	1.994 (19)	2.9494 (17)	164.5 (16)
N41C—H42C···O11Biii	0.930 (18)	2.120 (19)	3.0122 (17)	160.3 (16)
O11A—H11A···O12B	1.00 (2)	1.57 (2)	2.5635 (15)	173 (2)
O21B—H21B···O41Civ	0.99 (2)	1.58 (2)	2.5644 (14)	171 (2)
O22A—H22A···O11Bi	0.90 (2)	1.65 (2)	2.5363 (17)	170.8 (18)
C3B—H3B···O11Av	0.93	2.55	3.365 (2)	146
C4C—H4C···O11Biii	0.98	2.53	3.2159 (17)	127
C2C—H21C···O12A	0.97	2.54	3.317 (2)	137
C2C—H21C···O12B	0.97	2.55	3.364 (2)	142
C6C—H62C···O21Bi	0.97	2.47	3.4265 (19)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1C—H11C⋯O21A	0.932 (19)	1.911 (19)	2.8287 (18)	167.7 (16)
N1C—H12C⋯O12Ai	0.953 (18)	2.077 (17)	2.8519 (16)	137.4 (14)
N1C—H12C⋯O12Bi	0.953 (18)	2.204 (17)	2.9606 (16)	135.6 (14)
N41C—H41C⋯O22Bii	0.979 (19)	1.994 (19)	2.9494 (17)	164.5 (16)
N41C—H42C⋯O11Biii	0.930 (18)	2.120 (19)	3.0122 (17)	160.3 (16)
O11A—H11A⋯O12B	1.00 (2)	1.57 (2)	2.5635 (15)	173 (2)
O21B—H21B⋯O41Civ	0.99 (2)	1.58 (2)	2.5644 (14)	171 (2)
O22A—H22A⋯O11Bi	0.90 (2)	1.65 (2)	2.5363 (17)	170.8 (18)

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