2-Amino-5-chloro-pyridinium 2-carb-oxy-acetate.

The title salt, C(5)H(6)ClN(2) (+)·C(3)H(3)O(4) (-), contains two cations and two anions in the asymmetric unit. Both 2-amino-5-chloro-pyridinium ions are protonated at their pyridine N atoms and both hydrogen malonate ions feature an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring motif and results in a folded conformation. In the crystal structure, the cations and anions are linked via N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, forming chains propagating in [010], which are cross-linked by further C-H⋯O inter-actions.

Related literature

For background to the chemistry of substituted pyridines, see: Amr et al. (2006 ▶); Bart et al. (2001 ▶); Shinkai et al. (2000 ▶); Klimesôva et al. (1999 ▶). For related structures, see: Pourayoubi et al. (2007 ▶); Janczak & Perpétuo (2009 ▶); Akriche & Rzaigui (2005 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H6ClN2 +·C3H3O4 −

M = 232.62

Monoclinic,

a = 15.6971 (19) Å

b = 16.866 (2) Å

c = 7.4662 (10) Å

β = 94.518 (3)°

V = 1970.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.38 mm−1

T = 100 K

0.22 × 0.14 × 0.07 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.921, T max = 0.973

22474 measured reflections

5811 independent reflections

4314 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.01

5811 reflections

343 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.29 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: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019677/hb5466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019677/hb5466Isup2.hkl

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

C5H6ClN2+·C3H3O4−	F(000) = 960
Mr = 232.62	Dx = 1.568 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3966 reflections
a = 15.6971 (19) Å	θ = 2.6–29.5°
b = 16.866 (2) Å	µ = 0.38 mm−1
c = 7.4662 (10) Å	T = 100 K
β = 94.518 (3)°	Needle, colourless
V = 1970.5 (4) Å3	0.22 × 0.14 × 0.07 mm
Z = 8

Bruker APEXII DUO CCD diffractometer	5811 independent reflections
Radiation source: fine-focus sealed tube	4314 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 30.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
Tmin = 0.921, Tmax = 0.973	k = −23→23
22474 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.3626P] where P = (Fo2 + 2Fc2)/3
5811 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1A	1.10339 (2)	0.51132 (2)	0.62925 (6)	0.02059 (10)
N1A	0.96753 (8)	0.70248 (8)	0.71311 (18)	0.0154 (3)
N2A	0.98853 (9)	0.83754 (8)	0.6948 (2)	0.0201 (3)
C1A	0.99204 (10)	0.62574 (9)	0.7005 (2)	0.0158 (3)
C2A	1.07092 (10)	0.60860 (9)	0.6478 (2)	0.0161 (3)
C3A	1.12584 (10)	0.67048 (10)	0.6084 (2)	0.0185 (3)
C4A	1.10044 (10)	0.74747 (9)	0.6221 (2)	0.0183 (3)
C5A	1.01808 (10)	0.76410 (9)	0.6772 (2)	0.0153 (3)
O1A	0.80991 (7)	0.72010 (7)	0.78892 (17)	0.0217 (3)
O2A	0.82767 (7)	0.84610 (6)	0.87375 (16)	0.0188 (2)
O3A	0.59603 (7)	0.85002 (7)	1.08754 (16)	0.0210 (3)
O4A	0.71363 (7)	0.91411 (7)	1.02782 (17)	0.0202 (2)
C6A	0.78450 (10)	0.78253 (9)	0.8570 (2)	0.0152 (3)
C7A	0.69498 (10)	0.78000 (9)	0.9200 (2)	0.0150 (3)
C8A	0.66443 (10)	0.85090 (9)	1.0200 (2)	0.0156 (3)
Cl1B	0.63656 (3)	0.19876 (2)	0.73072 (6)	0.02333 (10)
N1B	0.49352 (8)	0.38598 (8)	0.80976 (18)	0.0157 (3)
N2B	0.50075 (9)	0.51989 (8)	0.7476 (2)	0.0208 (3)
C1B	0.52319 (10)	0.31042 (9)	0.8071 (2)	0.0164 (3)
C2B	0.59873 (10)	0.29500 (10)	0.7381 (2)	0.0175 (3)
C3B	0.64554 (10)	0.35768 (10)	0.6699 (2)	0.0200 (3)
C4B	0.61446 (10)	0.43307 (10)	0.6713 (2)	0.0192 (3)
C5B	0.53518 (10)	0.44787 (9)	0.7429 (2)	0.0162 (3)
O1B	0.34096 (7)	0.39509 (6)	0.92022 (17)	0.0215 (3)
O2B	0.33226 (7)	0.52644 (6)	0.89745 (17)	0.0209 (3)
O3B	0.10788 (7)	0.53283 (7)	1.13690 (18)	0.0270 (3)
O4B	0.21003 (7)	0.59797 (7)	1.01198 (17)	0.0213 (3)
C6B	0.30412 (10)	0.45958 (9)	0.9424 (2)	0.0157 (3)
C7B	0.22061 (10)	0.45532 (9)	1.0316 (2)	0.0163 (3)
C8B	0.17473 (10)	0.53207 (9)	1.0644 (2)	0.0172 (3)
H1A	0.9511 (11)	0.5865 (11)	0.730 (2)	0.016 (4)*
H1B	0.4871 (12)	0.2697 (12)	0.856 (3)	0.026 (5)*
H3A	1.1788 (13)	0.6612 (11)	0.572 (3)	0.025 (5)*
H3B	0.7003 (13)	0.3485 (11)	0.623 (3)	0.026 (5)*
H4A	1.1372 (13)	0.7899 (12)	0.597 (3)	0.028 (5)*
H4B	0.6435 (13)	0.4767 (12)	0.626 (3)	0.026 (5)*
H7AA	0.6570 (12)	0.7744 (11)	0.815 (3)	0.023 (5)*
H7AB	0.6906 (13)	0.7322 (12)	0.991 (3)	0.029 (5)*
H7BA	0.1847 (14)	0.4223 (13)	0.967 (3)	0.035 (6)*
H7BB	0.2294 (13)	0.4291 (12)	1.145 (3)	0.031 (6)*
H1NA	0.9120 (14)	0.7144 (13)	0.738 (3)	0.035 (6)*
H2NA	0.9348 (14)	0.8461 (12)	0.743 (3)	0.033 (6)*
H3NA	1.0235 (14)	0.8762 (14)	0.680 (3)	0.041 (6)*
H1NB	0.4410 (14)	0.3956 (12)	0.851 (3)	0.034 (6)*
H2NB	0.4509 (13)	0.5249 (12)	0.793 (3)	0.028 (5)*
H3NB	0.5290 (14)	0.5628 (14)	0.702 (3)	0.038 (6)*
H1OA	0.7643 (16)	0.8995 (15)	0.976 (3)	0.051 (7)*
H1OB	0.2602 (17)	0.5811 (16)	0.965 (4)	0.058 (8)*

	U11	U22	U33	U12	U13	U23
Cl1A	0.02137 (19)	0.01383 (18)	0.0268 (2)	0.00466 (14)	0.00314 (16)	−0.00142 (16)
N1A	0.0130 (6)	0.0137 (6)	0.0202 (7)	−0.0002 (5)	0.0045 (5)	−0.0004 (5)
N2A	0.0188 (7)	0.0131 (7)	0.0292 (8)	−0.0008 (5)	0.0074 (6)	0.0005 (6)
C1A	0.0172 (7)	0.0120 (7)	0.0182 (7)	−0.0011 (6)	0.0025 (6)	−0.0002 (6)
C2A	0.0172 (7)	0.0128 (7)	0.0182 (7)	0.0019 (5)	0.0016 (6)	−0.0007 (6)
C3A	0.0134 (7)	0.0198 (8)	0.0228 (8)	0.0008 (6)	0.0054 (6)	−0.0010 (7)
C4A	0.0161 (7)	0.0156 (7)	0.0238 (8)	−0.0030 (6)	0.0054 (6)	0.0015 (6)
C5A	0.0165 (7)	0.0147 (7)	0.0149 (7)	−0.0015 (5)	0.0018 (6)	0.0004 (6)
O1A	0.0173 (5)	0.0146 (5)	0.0346 (7)	−0.0007 (4)	0.0101 (5)	−0.0051 (5)
O2A	0.0185 (5)	0.0132 (5)	0.0255 (6)	−0.0037 (4)	0.0074 (5)	−0.0022 (5)
O3A	0.0193 (5)	0.0195 (6)	0.0250 (6)	0.0019 (4)	0.0080 (5)	−0.0011 (5)
O4A	0.0225 (6)	0.0123 (5)	0.0272 (6)	−0.0009 (4)	0.0096 (5)	−0.0026 (5)
C6A	0.0155 (7)	0.0137 (7)	0.0165 (7)	0.0004 (5)	0.0023 (6)	0.0013 (6)
C7A	0.0150 (7)	0.0122 (7)	0.0178 (7)	−0.0013 (5)	0.0023 (6)	−0.0001 (6)
C8A	0.0187 (7)	0.0128 (7)	0.0154 (7)	0.0016 (5)	0.0026 (6)	0.0025 (6)
Cl1B	0.0262 (2)	0.0190 (2)	0.0250 (2)	0.00833 (15)	0.00331 (16)	0.00035 (17)
N1B	0.0148 (6)	0.0144 (6)	0.0184 (6)	−0.0006 (5)	0.0038 (5)	0.0001 (5)
N2B	0.0198 (7)	0.0146 (7)	0.0288 (8)	−0.0001 (5)	0.0081 (6)	0.0015 (6)
C1B	0.0177 (7)	0.0140 (7)	0.0174 (7)	−0.0003 (6)	0.0011 (6)	0.0013 (6)
C2B	0.0191 (7)	0.0166 (7)	0.0164 (7)	0.0037 (6)	−0.0006 (6)	−0.0007 (6)
C3B	0.0161 (7)	0.0249 (8)	0.0195 (8)	0.0010 (6)	0.0053 (6)	−0.0024 (7)
C4B	0.0176 (7)	0.0194 (8)	0.0212 (8)	−0.0032 (6)	0.0061 (6)	−0.0009 (7)
C5B	0.0176 (7)	0.0148 (7)	0.0162 (7)	−0.0025 (6)	0.0015 (6)	−0.0010 (6)
O1B	0.0192 (5)	0.0124 (5)	0.0342 (7)	0.0012 (4)	0.0110 (5)	0.0018 (5)
O2B	0.0208 (6)	0.0119 (5)	0.0312 (7)	−0.0005 (4)	0.0094 (5)	0.0013 (5)
O3B	0.0246 (6)	0.0194 (6)	0.0392 (8)	0.0045 (5)	0.0157 (6)	0.0017 (6)
O4B	0.0199 (6)	0.0128 (5)	0.0321 (7)	0.0012 (4)	0.0082 (5)	−0.0002 (5)
C6B	0.0162 (7)	0.0137 (7)	0.0175 (7)	0.0013 (5)	0.0024 (6)	−0.0002 (6)
C7B	0.0170 (7)	0.0113 (7)	0.0212 (8)	0.0015 (5)	0.0054 (6)	0.0016 (6)
C8B	0.0178 (7)	0.0147 (7)	0.0193 (8)	0.0020 (6)	0.0016 (6)	0.0005 (6)

Cl1A—C2A	1.7268 (16)	Cl1B—C2B	1.7308 (16)
N1A—C5A	1.3472 (19)	N1B—C5B	1.3484 (19)
N1A—C1A	1.3557 (19)	N1B—C1B	1.358 (2)
N1A—H1NA	0.93 (2)	N1B—H1NB	0.92 (2)
N2A—C5A	1.333 (2)	N2B—C5B	1.331 (2)
N2A—H2NA	0.95 (2)	N2B—H2NB	0.88 (2)
N2A—H3NA	0.87 (2)	N2B—H3NB	0.93 (2)
C1A—C2A	1.360 (2)	C1B—C2B	1.355 (2)
C1A—H1A	0.959 (18)	C1B—H1B	0.98 (2)
C2A—C3A	1.400 (2)	C2B—C3B	1.406 (2)
C3A—C4A	1.365 (2)	C3B—C4B	1.362 (2)
C3A—H3A	0.91 (2)	C3B—H3B	0.96 (2)
C4A—C5A	1.415 (2)	C4B—C5B	1.415 (2)
C4A—H4A	0.95 (2)	C4B—H4B	0.94 (2)
O1A—C6A	1.2481 (18)	O1B—C6B	1.2491 (18)
O2A—C6A	1.2692 (18)	O2B—C6B	1.2660 (19)
O3A—C8A	1.2217 (19)	O3B—C8B	1.2181 (19)
O4A—C8A	1.3150 (18)	O4B—C8B	1.3153 (19)
O4A—H1OA	0.94 (3)	O4B—H1OB	0.93 (3)
C6A—C7A	1.517 (2)	C6B—C7B	1.518 (2)
C7A—C8A	1.508 (2)	C7B—C8B	1.511 (2)
C7A—H7AA	0.95 (2)	C7B—H7BA	0.90 (2)
C7A—H7AB	0.97 (2)	C7B—H7BB	0.95 (2)
C5A—N1A—C1A	123.22 (13)	C5B—N1B—C1B	122.97 (14)
C5A—N1A—H1NA	116.7 (13)	C5B—N1B—H1NB	117.6 (13)
C1A—N1A—H1NA	119.8 (13)	C1B—N1B—H1NB	119.3 (13)
C5A—N2A—H2NA	120.2 (13)	C5B—N2B—H2NB	118.2 (13)
C5A—N2A—H3NA	117.3 (15)	C5B—N2B—H3NB	119.7 (14)
H2NA—N2A—H3NA	121.5 (19)	H2NB—N2B—H3NB	122.1 (19)
N1A—C1A—C2A	119.54 (14)	C2B—C1B—N1B	119.84 (15)
N1A—C1A—H1A	116.4 (11)	C2B—C1B—H1B	123.8 (12)
C2A—C1A—H1A	124.1 (11)	N1B—C1B—H1B	116.4 (12)
C1A—C2A—C3A	119.49 (14)	C1B—C2B—C3B	119.44 (15)
C1A—C2A—Cl1A	120.43 (12)	C1B—C2B—Cl1B	120.34 (13)
C3A—C2A—Cl1A	120.07 (12)	C3B—C2B—Cl1B	120.22 (12)
C4A—C3A—C2A	120.35 (14)	C4B—C3B—C2B	120.10 (15)
C4A—C3A—H3A	117.8 (12)	C4B—C3B—H3B	118.8 (12)
C2A—C3A—H3A	121.9 (12)	C2B—C3B—H3B	121.1 (12)
C3A—C4A—C5A	119.31 (14)	C3B—C4B—C5B	119.59 (15)
C3A—C4A—H4A	121.2 (12)	C3B—C4B—H4B	122.9 (12)
C5A—C4A—H4A	119.5 (12)	C5B—C4B—H4B	117.5 (12)
N2A—C5A—N1A	118.84 (14)	N2B—C5B—N1B	119.12 (14)
N2A—C5A—C4A	123.08 (14)	N2B—C5B—C4B	122.84 (15)
N1A—C5A—C4A	118.08 (14)	N1B—C5B—C4B	118.04 (14)
C8A—O4A—H1OA	106.3 (15)	C8B—O4B—H1OB	104.0 (16)
O1A—C6A—O2A	124.57 (14)	O1B—C6B—O2B	124.45 (14)
O1A—C6A—C7A	115.85 (13)	O1B—C6B—C7B	116.22 (13)
O2A—C6A—C7A	119.57 (13)	O2B—C6B—C7B	119.33 (13)
C8A—C7A—C6A	118.02 (13)	C8B—C7B—C6B	118.02 (13)
C8A—C7A—H7AA	106.5 (12)	C8B—C7B—H7BA	109.3 (13)
C6A—C7A—H7AA	106.5 (12)	C6B—C7B—H7BA	108.6 (13)
C8A—C7A—H7AB	110.6 (12)	C8B—C7B—H7BB	106.9 (12)
C6A—C7A—H7AB	107.4 (12)	C6B—C7B—H7BB	109.9 (12)
H7AA—C7A—H7AB	107.4 (16)	H7BA—C7B—H7BB	103.1 (18)
O3A—C8A—O4A	121.58 (14)	O3B—C8B—O4B	121.41 (14)
O3A—C8A—C7A	121.26 (14)	O3B—C8B—C7B	121.29 (14)
O4A—C8A—C7A	117.15 (13)	O4B—C8B—C7B	117.29 (13)
C5A—N1A—C1A—C2A	−0.6 (2)	C5B—N1B—C1B—C2B	1.4 (2)
N1A—C1A—C2A—C3A	0.4 (2)	N1B—C1B—C2B—C3B	0.0 (2)
N1A—C1A—C2A—Cl1A	−179.58 (12)	N1B—C1B—C2B—Cl1B	−179.02 (12)
C1A—C2A—C3A—C4A	−0.2 (3)	C1B—C2B—C3B—C4B	−0.8 (3)
Cl1A—C2A—C3A—C4A	179.75 (14)	Cl1B—C2B—C3B—C4B	178.16 (13)
C2A—C3A—C4A—C5A	0.2 (3)	C2B—C3B—C4B—C5B	0.4 (3)
C1A—N1A—C5A—N2A	−179.49 (15)	C1B—N1B—C5B—N2B	178.66 (15)
C1A—N1A—C5A—C4A	0.6 (2)	C1B—N1B—C5B—C4B	−1.7 (2)
C3A—C4A—C5A—N2A	179.68 (17)	C3B—C4B—C5B—N2B	−179.60 (16)
C3A—C4A—C5A—N1A	−0.4 (2)	C3B—C4B—C5B—N1B	0.8 (2)
O1A—C6A—C7A—C8A	173.93 (14)	O1B—C6B—C7B—C8B	178.82 (15)
O2A—C6A—C7A—C8A	−6.9 (2)	O2B—C6B—C7B—C8B	−0.5 (2)
C6A—C7A—C8A—O3A	−173.71 (15)	C6B—C7B—C8B—O3B	−179.34 (16)
C6A—C7A—C8A—O4A	7.8 (2)	C6B—C7B—C8B—O4B	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1A	0.93 (2)	1.68 (2)	2.5982 (17)	171 (2)
N2A—H2NA···O2A	0.95 (2)	2.01 (2)	2.9518 (19)	169.1 (18)
N2A—H3NA···O3Bi	0.87 (2)	2.07 (2)	2.9333 (18)	178 (2)
N1B—H1NB···O1B	0.92 (2)	1.69 (2)	2.5980 (17)	169 (2)
N2B—H2NB···O2B	0.88 (2)	2.08 (2)	2.9538 (19)	175 (2)
N2B—H3NB···O3Aii	0.93 (2)	2.04 (2)	2.9598 (19)	175 (2)
O4A—H1OA···O2A	0.94 (2)	1.58 (2)	2.4835 (16)	158 (2)
O4B—H1OB···O2B	0.93 (3)	1.57 (3)	2.4752 (16)	162 (3)
C1A—H1A···O3Biii	0.960 (18)	2.458 (18)	3.374 (2)	159.6 (14)
C1B—H1B···O3Aiii	0.98 (2)	2.46 (2)	3.417 (2)	166.1 (18)
C7A—H7AB···O1Biii	0.97 (2)	2.31 (2)	3.2509 (19)	162.6 (18)
C7B—H7BB···O4Aiv	0.96 (2)	2.55 (2)	3.440 (2)	155.7 (16)
C4A—H4A···O4Bi	0.95 (2)	2.32 (2)	3.264 (2)	171.6 (18)
C4B—H4B···O4Aii	0.94 (2)	2.30 (2)	3.237 (2)	177.4 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1A	0.93 (2)	1.68 (2)	2.5982 (17)	171 (2)
N2A—H2NA⋯O2A	0.95 (2)	2.01 (2)	2.9518 (19)	169.1 (18)
N2A—H3NA⋯O3Bi	0.87 (2)	2.07 (2)	2.9333 (18)	178 (2)
N1B—H1NB⋯O1B	0.92 (2)	1.69 (2)	2.5980 (17)	169 (2)
N2B—H2NB⋯O2B	0.88 (2)	2.08 (2)	2.9538 (19)	175 (2)
N2B—H3NB⋯O3Aii	0.93 (2)	2.04 (2)	2.9598 (19)	175 (2)
O4A—H1OA⋯O2A	0.94 (2)	1.58 (2)	2.4835 (16)	158 (2)
O4B—H1OB⋯O2B	0.93 (3)	1.57 (3)	2.4752 (16)	162 (3)
C1A—H1A⋯O3Biii	0.960 (18)	2.458 (18)	3.374 (2)	159.6 (14)
C1B—H1B⋯O3Aiii	0.98 (2)	2.46 (2)	3.417 (2)	166.1 (18)
C7A—H7AB⋯O1Biii	0.97 (2)	2.31 (2)	3.2509 (19)	162.6 (18)
C7B—H7BB⋯O4Aiv	0.96 (2)	2.55 (2)	3.440 (2)	155.7 (16)
C4A—H4A⋯O4Bi	0.95 (2)	2.32 (2)	3.264 (2)	171.6 (18)
C4B—H4B⋯O4Aii	0.94 (2)	2.30 (2)	3.237 (2)	177.4 (17)

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