2-Amino-5-methyl-pyridinium picolinate 0.63-hydrate.

The asymmetric unit of the title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(2) (-)·0.63H(2)O, contains two crystallographically independent 2-amino-5-methyl-pyridinium cations, a pair of picolinate anions and two water mol-ecules, one with an occupancy of 0.25. Both the 2-amino-5-methyl-pyridine mol-ecules are protonated at the pyridine N atoms. In the crystal structure, the cations, anions and water mol-ecules are linked via N-H⋯O, N-H⋯N and O-H⋯O hydrogen bonds, as well as by C-H⋯O contacts, forming a chain along the b axis. In addition, weak π-π inter-actions are observed between pyridinium rings, with centroid-centroid distances of 3.5306 (13) Å.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶); Navarro Ranninger et al. (1985 ▶); Luque et al. (1997 ▶); Qin et al. (1999 ▶); Yip et al. (1999 ▶); Ren et al. (2002 ▶); Rivas et al. (2003 ▶); Jin et al. (2001 ▶); Albrecht et al. (2003 ▶); Nahringbauer & Kvick (1977 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For details of picolinic acid, see: Mahler & Cordes (1971 ▶); Ogata et al. (2000 ▶). 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

C6H9N2 +·C6H4NO2 −·0.63H2O

M = 242.51

Orthorhombic,

a = 12.126 (3) Å

b = 13.842 (3) Å

c = 14.318 (3) Å

V = 2403.4 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.28 × 0.20 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.973, T max = 0.991

50363 measured reflections

3955 independent reflections

3119 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.141

S = 1.09

3955 reflections

353 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.35 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/S1600536810018180/sj5005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018180/sj5005Isup2.hkl

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

C6H9N2+·C6H4NO2−·0.63H2O	F(000) = 1026
Mr = 242.51	Dx = 1.340 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7433 reflections
a = 12.126 (3) Å	θ = 2.2–29.8°
b = 13.842 (3) Å	µ = 0.10 mm−1
c = 14.318 (3) Å	T = 100 K
V = 2403.4 (10) Å3	Block, colourless
Z = 8	0.28 × 0.20 × 0.09 mm

Bruker APEXII DUO CCD area-detector diffractometer	3955 independent reflections
Radiation source: fine-focus sealed tube	3119 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 30.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.973, Tmax = 0.991	k = −19→19
50363 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0779P)2 + 0.4137P] where P = (Fo2 + 2Fc2)/3
3955 reflections	(Δ/σ)max = 0.001
353 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.35 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	Occ. (<1)
N1A	0.97657 (16)	0.86544 (15)	0.09594 (13)	0.0235 (4)
N2A	0.98590 (18)	0.69933 (17)	0.08274 (15)	0.0291 (5)
C1A	0.93479 (19)	0.78196 (18)	0.06311 (15)	0.0231 (4)
C2A	0.83756 (19)	0.78782 (18)	0.00781 (17)	0.0253 (5)
H2AA	0.8060	0.7319	−0.0162	0.030*
C3A	0.79046 (19)	0.87571 (18)	−0.01001 (17)	0.0257 (5)
H3AA	0.7273	0.8789	−0.0467	0.031*
C4A	0.83615 (19)	0.96169 (17)	0.02636 (17)	0.0247 (5)
C5A	0.92944 (19)	0.95332 (17)	0.07947 (16)	0.0238 (5)
H5AA	0.9613	1.0085	0.1048	0.029*
C6A	0.7824 (2)	1.05808 (19)	0.01044 (19)	0.0306 (5)
H6AA	0.8170	1.1058	0.0493	0.046*
H6AB	0.7055	1.0539	0.0258	0.046*
H6AC	0.7904	1.0761	−0.0539	0.046*
O1A	1.0576 (2)	0.51193 (14)	0.1466 (2)	0.0585 (8)
O2A	1.06051 (16)	0.35162 (13)	0.15326 (14)	0.0349 (4)
N3A	0.8965 (2)	0.50822 (17)	0.01507 (19)	0.0407 (6)
C7A	0.8132 (2)	0.5040 (2)	−0.0465 (2)	0.0425 (7)
H7AA	0.7946	0.5602	−0.0785	0.051*
C8A	0.7533 (2)	0.4213 (2)	−0.0653 (2)	0.0373 (6)
H8AA	0.6959	0.4219	−0.1084	0.045*
C9A	0.7809 (2)	0.3379 (2)	−0.0184 (2)	0.0332 (6)
H9AA	0.7420	0.2811	−0.0288	0.040*
C10A	0.8683 (2)	0.34009 (19)	0.04496 (18)	0.0280 (5)
H10A	0.8890	0.2846	0.0771	0.034*
C11A	0.9239 (2)	0.42690 (18)	0.05917 (18)	0.0282 (5)
C12A	1.0218 (2)	0.43223 (19)	0.1257 (2)	0.0319 (5)
N1B	0.24603 (16)	0.35896 (15)	0.24965 (14)	0.0233 (4)
N2B	0.25938 (19)	0.52545 (16)	0.24544 (15)	0.0271 (4)
C1B	0.29982 (19)	0.44099 (17)	0.27328 (16)	0.0230 (4)
C2B	0.39853 (18)	0.43069 (17)	0.32614 (17)	0.0251 (5)
H2BA	0.4384	0.4851	0.3438	0.030*
C3B	0.4344 (2)	0.34168 (19)	0.35063 (18)	0.0280 (5)
H3BA	0.4989	0.3362	0.3853	0.034*
C4B	0.3767 (2)	0.25626 (18)	0.32509 (17)	0.0276 (5)
C5B	0.2821 (2)	0.26944 (17)	0.27415 (17)	0.0251 (5)
H5BA	0.2415	0.2157	0.2559	0.030*
C6B	0.4152 (3)	0.15790 (19)	0.3523 (2)	0.0392 (7)
H6BA	0.3732	0.1102	0.3191	0.059*
H6BB	0.4052	0.1491	0.4182	0.059*
H6BC	0.4919	0.1511	0.3371	0.059*
O1B	0.16897 (15)	0.71003 (12)	0.20473 (13)	0.0300 (4)
O2B	0.16686 (15)	0.87068 (13)	0.18961 (13)	0.0310 (4)
N3B	0.35568 (17)	0.71727 (15)	0.30874 (15)	0.0279 (4)
C7B	0.4429 (2)	0.72461 (19)	0.3658 (2)	0.0358 (6)
H7BA	0.4767	0.6679	0.3857	0.043*
C8B	0.4858 (2)	0.8121 (2)	0.3969 (2)	0.0373 (6)
H8BA	0.5458	0.8134	0.4373	0.045*
C9B	0.4378 (2)	0.89624 (19)	0.36688 (19)	0.0332 (6)
H9BA	0.4650	0.9558	0.3860	0.040*
C10B	0.3477 (2)	0.89054 (18)	0.30724 (17)	0.0271 (5)
H10B	0.3142	0.9465	0.2851	0.033*
C11B	0.30822 (18)	0.80070 (17)	0.28102 (16)	0.0227 (4)
C12B	0.20592 (18)	0.79216 (17)	0.21971 (16)	0.0222 (4)
O1W	0.1654 (5)	0.0578 (4)	0.2767 (5)	0.0227 (12)	0.25
H1W1	0.1196	0.0966	0.2937	0.034*	0.25
H2W1	0.1398	0.0069	0.2582	0.034*	0.25
O2W	0.0279 (3)	0.15220 (18)	0.17835 (19)	0.0758 (10)
H1W2	−0.0219	0.1402	0.2150	0.114*
H2W2	0.0312	0.2103	0.1667	0.114*
H1NA	1.044 (3)	0.858 (3)	0.131 (3)	0.050 (10)*
H2NA	1.049 (3)	0.702 (3)	0.124 (3)	0.060 (11)*
H3NA	0.959 (3)	0.638 (2)	0.064 (2)	0.034 (8)*
H1NB	0.177 (3)	0.359 (3)	0.219 (3)	0.061 (11)*
H2NB	0.292 (3)	0.574 (2)	0.263 (2)	0.037 (9)*
H3NB	0.193 (3)	0.525 (3)	0.212 (2)	0.045 (9)*

	U11	U22	U33	U12	U13	U23
N1A	0.0208 (9)	0.0264 (10)	0.0232 (9)	0.0005 (8)	−0.0022 (8)	0.0015 (8)
N2A	0.0295 (10)	0.0258 (11)	0.0318 (11)	0.0013 (9)	−0.0059 (9)	0.0014 (9)
C1A	0.0233 (10)	0.0254 (11)	0.0206 (10)	0.0000 (9)	0.0007 (9)	0.0010 (9)
C2A	0.0242 (10)	0.0245 (11)	0.0274 (11)	−0.0028 (9)	−0.0029 (9)	−0.0013 (9)
C3A	0.0205 (10)	0.0314 (12)	0.0253 (11)	−0.0022 (9)	−0.0019 (9)	0.0026 (9)
C4A	0.0231 (10)	0.0248 (11)	0.0263 (11)	0.0013 (9)	0.0032 (9)	0.0031 (9)
C5A	0.0240 (10)	0.0217 (11)	0.0257 (11)	−0.0007 (9)	0.0002 (9)	−0.0008 (9)
C6A	0.0275 (11)	0.0281 (12)	0.0361 (13)	0.0001 (10)	−0.0007 (10)	0.0047 (11)
O1A	0.0586 (14)	0.0248 (10)	0.0922 (19)	−0.0069 (10)	−0.0532 (14)	0.0083 (11)
O2A	0.0308 (9)	0.0263 (9)	0.0475 (11)	−0.0005 (7)	−0.0147 (8)	0.0024 (8)
N3A	0.0420 (13)	0.0305 (12)	0.0495 (14)	−0.0023 (10)	−0.0252 (12)	0.0033 (11)
C7A	0.0435 (16)	0.0355 (15)	0.0483 (16)	0.0052 (13)	−0.0225 (14)	0.0034 (13)
C8A	0.0311 (13)	0.0435 (16)	0.0373 (14)	0.0067 (12)	−0.0122 (11)	−0.0120 (12)
C9A	0.0267 (12)	0.0338 (14)	0.0392 (14)	−0.0009 (10)	−0.0045 (11)	−0.0136 (11)
C10A	0.0242 (11)	0.0293 (12)	0.0305 (12)	0.0010 (10)	0.0006 (9)	−0.0032 (10)
C11A	0.0265 (11)	0.0263 (12)	0.0318 (12)	−0.0001 (10)	−0.0057 (10)	−0.0009 (10)
C12A	0.0298 (12)	0.0253 (12)	0.0407 (14)	−0.0018 (10)	−0.0125 (11)	0.0017 (11)
N1B	0.0228 (9)	0.0216 (10)	0.0255 (9)	0.0017 (8)	−0.0028 (8)	−0.0009 (8)
N2B	0.0292 (10)	0.0215 (10)	0.0305 (11)	0.0005 (9)	−0.0057 (9)	0.0004 (8)
C1B	0.0225 (10)	0.0235 (11)	0.0230 (10)	0.0006 (9)	0.0019 (8)	0.0003 (9)
C2B	0.0209 (10)	0.0249 (11)	0.0294 (12)	−0.0010 (9)	−0.0036 (9)	−0.0018 (9)
C3B	0.0246 (11)	0.0298 (13)	0.0295 (12)	0.0024 (9)	−0.0051 (9)	0.0019 (10)
C4B	0.0300 (12)	0.0246 (11)	0.0281 (11)	0.0028 (10)	−0.0030 (10)	0.0016 (9)
C5B	0.0277 (11)	0.0208 (11)	0.0268 (11)	−0.0004 (9)	−0.0017 (9)	−0.0001 (9)
C6B	0.0436 (15)	0.0250 (12)	0.0490 (16)	0.0054 (12)	−0.0147 (13)	0.0054 (12)
O1B	0.0288 (8)	0.0233 (8)	0.0378 (10)	0.0010 (7)	−0.0088 (8)	−0.0037 (7)
O2B	0.0280 (8)	0.0267 (9)	0.0382 (10)	−0.0038 (7)	−0.0098 (8)	0.0084 (8)
N3B	0.0256 (10)	0.0254 (10)	0.0327 (10)	−0.0018 (8)	−0.0074 (8)	0.0038 (8)
C7B	0.0348 (13)	0.0256 (13)	0.0470 (15)	−0.0031 (11)	−0.0183 (12)	0.0069 (11)
C8B	0.0367 (13)	0.0322 (14)	0.0432 (15)	−0.0102 (12)	−0.0176 (12)	0.0065 (12)
C9B	0.0376 (14)	0.0236 (12)	0.0385 (14)	−0.0115 (10)	−0.0126 (12)	0.0055 (11)
C10B	0.0294 (12)	0.0200 (11)	0.0320 (12)	−0.0043 (9)	−0.0048 (10)	0.0048 (9)
C11B	0.0207 (10)	0.0246 (11)	0.0227 (10)	−0.0032 (9)	0.0004 (8)	0.0026 (9)
C12B	0.0206 (9)	0.0237 (11)	0.0222 (10)	−0.0007 (9)	0.0007 (8)	0.0016 (9)
O1W	0.018 (3)	0.017 (3)	0.032 (3)	0.000 (2)	0.005 (3)	−0.001 (3)
O2W	0.122 (3)	0.0424 (13)	0.0626 (15)	−0.0350 (16)	0.0451 (17)	−0.0191 (12)

N1A—C1A	1.347 (3)	N1B—H1NB	0.95 (4)
N1A—C5A	1.365 (3)	N2B—C1B	1.329 (3)
N1A—H1NA	0.97 (4)	N2B—H2NB	0.82 (3)
N2A—C1A	1.331 (3)	N2B—H3NB	0.93 (3)
N2A—H2NA	0.96 (4)	C1B—C2B	1.423 (3)
N2A—H3NA	0.94 (3)	C2B—C3B	1.353 (3)
C1A—C2A	1.423 (3)	C2B—H2BA	0.9300
C2A—C3A	1.368 (3)	C3B—C4B	1.421 (4)
C2A—H2AA	0.9300	C3B—H3BA	0.9300
C3A—C4A	1.412 (3)	C4B—C5B	1.371 (3)
C3A—H3AA	0.9300	C4B—C6B	1.491 (3)
C4A—C5A	1.368 (3)	C5B—H5BA	0.9300
C4A—C6A	1.502 (3)	C6B—H6BA	0.9600
C5A—H5AA	0.9300	C6B—H6BB	0.9600
C6A—H6AA	0.9600	C6B—H6BC	0.9600
C6A—H6AB	0.9600	O1B—C12B	1.241 (3)
C6A—H6AC	0.9600	O2B—C12B	1.262 (3)
O1A—C12A	1.223 (3)	N3B—C7B	1.340 (3)
O2A—C12A	1.273 (3)	N3B—C11B	1.350 (3)
N3A—C11A	1.333 (3)	C7B—C8B	1.391 (4)
N3A—C7A	1.343 (3)	C7B—H7BA	0.9300
C7A—C8A	1.382 (4)	C8B—C9B	1.372 (4)
C7A—H7AA	0.9300	C8B—H8BA	0.9300
C8A—C9A	1.376 (4)	C9B—C10B	1.389 (3)
C8A—H8AA	0.9300	C9B—H9BA	0.9300
C9A—C10A	1.395 (3)	C10B—C11B	1.384 (3)
C9A—H9AA	0.9300	C10B—H10B	0.9300
C10A—C11A	1.393 (3)	C11B—C12B	1.524 (3)
C10A—H10A	0.9300	O1W—H1W1	0.8098
C11A—C12A	1.523 (3)	O1W—H2W1	0.8148
N1B—C1B	1.353 (3)	O2W—H1W2	0.8172
N1B—C5B	1.360 (3)	O2W—H2W2	0.8226
C1A—N1A—C5A	123.2 (2)	C1B—N1B—H1NB	123 (2)
C1A—N1A—H1NA	114 (2)	C5B—N1B—H1NB	114 (2)
C5A—N1A—H1NA	122 (2)	C1B—N2B—H2NB	117 (2)
C1A—N2A—H2NA	118 (2)	C1B—N2B—H3NB	117 (2)
C1A—N2A—H3NA	123.3 (19)	H2NB—N2B—H3NB	126 (3)
H2NA—N2A—H3NA	119 (3)	N2B—C1B—N1B	119.1 (2)
N2A—C1A—N1A	119.2 (2)	N2B—C1B—C2B	123.9 (2)
N2A—C1A—C2A	123.5 (2)	N1B—C1B—C2B	117.0 (2)
N1A—C1A—C2A	117.2 (2)	C3B—C2B—C1B	119.9 (2)
C3A—C2A—C1A	120.0 (2)	C3B—C2B—H2BA	120.0
C3A—C2A—H2AA	120.0	C1B—C2B—H2BA	120.0
C1A—C2A—H2AA	120.0	C2B—C3B—C4B	122.2 (2)
C2A—C3A—C4A	121.1 (2)	C2B—C3B—H3BA	118.9
C2A—C3A—H3AA	119.4	C4B—C3B—H3BA	118.9
C4A—C3A—H3AA	119.4	C5B—C4B—C3B	116.0 (2)
C5A—C4A—C3A	117.3 (2)	C5B—C4B—C6B	121.5 (2)
C5A—C4A—C6A	121.2 (2)	C3B—C4B—C6B	122.6 (2)
C3A—C4A—C6A	121.5 (2)	N1B—C5B—C4B	121.8 (2)
N1A—C5A—C4A	121.2 (2)	N1B—C5B—H5BA	119.1
N1A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.1
C4A—C5A—H5AA	119.4	C4B—C6B—H6BA	109.5
C4A—C6A—H6AA	109.5	C4B—C6B—H6BB	109.5
C4A—C6A—H6AB	109.5	H6BA—C6B—H6BB	109.5
H6AA—C6A—H6AB	109.5	C4B—C6B—H6BC	109.5
C4A—C6A—H6AC	109.5	H6BA—C6B—H6BC	109.5
H6AA—C6A—H6AC	109.5	H6BB—C6B—H6BC	109.5
H6AB—C6A—H6AC	109.5	C7B—N3B—C11B	116.8 (2)
C11A—N3A—C7A	117.5 (2)	N3B—C7B—C8B	123.8 (2)
N3A—C7A—C8A	124.0 (3)	N3B—C7B—H7BA	118.1
N3A—C7A—H7AA	118.0	C8B—C7B—H7BA	118.1
C8A—C7A—H7AA	118.0	C9B—C8B—C7B	118.7 (2)
C9A—C8A—C7A	118.1 (2)	C9B—C8B—H8BA	120.7
C9A—C8A—H8AA	120.9	C7B—C8B—H8BA	120.7
C7A—C8A—H8AA	120.9	C8B—C9B—C10B	118.6 (2)
C8A—C9A—C10A	119.0 (2)	C8B—C9B—H9BA	120.7
C8A—C9A—H9AA	120.5	C10B—C9B—H9BA	120.7
C10A—C9A—H9AA	120.5	C11B—C10B—C9B	119.3 (2)
C11A—C10A—C9A	118.8 (2)	C11B—C10B—H10B	120.3
C11A—C10A—H10A	120.6	C9B—C10B—H10B	120.3
C9A—C10A—H10A	120.6	N3B—C11B—C10B	122.8 (2)
N3A—C11A—C10A	122.6 (2)	N3B—C11B—C12B	116.7 (2)
N3A—C11A—C12A	116.7 (2)	C10B—C11B—C12B	120.5 (2)
C10A—C11A—C12A	120.7 (2)	O1B—C12B—O2B	126.5 (2)
O1A—C12A—O2A	125.7 (2)	O1B—C12B—C11B	117.7 (2)
O1A—C12A—C11A	118.3 (2)	O2B—C12B—C11B	115.8 (2)
O2A—C12A—C11A	116.0 (2)	H1W1—O1W—H2W1	114.2
C1B—N1B—C5B	123.0 (2)	H1W2—O2W—H2W2	111.4
C5A—N1A—C1A—N2A	−179.8 (2)	C5B—N1B—C1B—N2B	179.2 (2)
C5A—N1A—C1A—C2A	0.8 (3)	C5B—N1B—C1B—C2B	0.1 (3)
N2A—C1A—C2A—C3A	−179.4 (2)	N2B—C1B—C2B—C3B	−179.2 (2)
N1A—C1A—C2A—C3A	0.0 (3)	N1B—C1B—C2B—C3B	−0.2 (3)
C1A—C2A—C3A—C4A	−0.6 (4)	C1B—C2B—C3B—C4B	0.2 (4)
C2A—C3A—C4A—C5A	0.4 (3)	C2B—C3B—C4B—C5B	−0.1 (4)
C2A—C3A—C4A—C6A	−177.5 (2)	C2B—C3B—C4B—C6B	−179.6 (3)
C1A—N1A—C5A—C4A	−1.0 (3)	C1B—N1B—C5B—C4B	0.0 (4)
C3A—C4A—C5A—N1A	0.4 (3)	C3B—C4B—C5B—N1B	0.0 (4)
C6A—C4A—C5A—N1A	178.3 (2)	C6B—C4B—C5B—N1B	179.5 (2)
C11A—N3A—C7A—C8A	1.3 (5)	C11B—N3B—C7B—C8B	0.0 (4)
N3A—C7A—C8A—C9A	−0.3 (5)	N3B—C7B—C8B—C9B	−1.1 (5)
C7A—C8A—C9A—C10A	−0.6 (4)	C7B—C8B—C9B—C10B	0.6 (4)
C8A—C9A—C10A—C11A	0.6 (4)	C8B—C9B—C10B—C11B	0.9 (4)
C7A—N3A—C11A—C10A	−1.4 (4)	C7B—N3B—C11B—C10B	1.6 (4)
C7A—N3A—C11A—C12A	177.5 (3)	C7B—N3B—C11B—C12B	−177.3 (2)
C9A—C10A—C11A—N3A	0.5 (4)	C9B—C10B—C11B—N3B	−2.1 (4)
C9A—C10A—C11A—C12A	−178.3 (2)	C9B—C10B—C11B—C12B	176.8 (2)
N3A—C11A—C12A—O1A	11.8 (4)	N3B—C11B—C12B—O1B	4.8 (3)
C10A—C11A—C12A—O1A	−169.3 (3)	C10B—C11B—C12B—O1B	−174.2 (2)
N3A—C11A—C12A—O2A	−166.9 (3)	N3B—C11B—C12B—O2B	−175.6 (2)
C10A—C11A—C12A—O2A	12.0 (4)	C10B—C11B—C12B—O2B	5.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2W2···O2Ai	0.82	2.00	2.812 (2)	170
N1A—H1NA···O2Bii	0.99 (2)	1.69 (2)	2.669 (2)	170 (2)
N2A—H2NA···O1Bii	0.94 (3)	1.89 (3)	2.829 (2)	178 (3)
N2A—H3NA···N3A	0.94 (3)	2.08 (3)	3.019 (3)	177 (2)
N1B—H1NB···O2Ai	0.96 (3)	1.68 (3)	2.642 (2)	173 (3)
N2B—H2NB···N3B	0.83 (3)	2.22 (3)	3.040 (2)	173 (2)
N2B—H3NB···O1Ai	0.93 (2)	1.90 (2)	2.831 (3)	175 (2)
C5A—H5AA···O2Wiii	0.93	2.39	3.319 (3)	175
C7A—H7AA···O2Biv	0.93	2.42	3.217 (3)	144
C8A—H8AA···O2Wv	0.93	2.50	3.339 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2W2⋯O2Ai	0.82	2.00	2.812 (2)	170
N1A—H1NA⋯O2Bii	0.99 (2)	1.69 (2)	2.669 (2)	170 (2)
N2A—H2NA⋯O1Bii	0.94 (3)	1.89 (3)	2.829 (2)	178 (3)
N2A—H3NA⋯N3A	0.94 (3)	2.08 (3)	3.019 (3)	177 (2)
N1B—H1NB⋯O2Ai	0.96 (3)	1.68 (3)	2.642 (2)	173 (3)
N2B—H2NB⋯N3B	0.83 (3)	2.22 (3)	3.040 (2)	173 (2)
N2B—H3NB⋯O1Ai	0.93 (2)	1.90 (2)	2.831 (3)	175 (2)
C5A—H5AA⋯O2Wiii	0.93	2.39	3.319 (3)	175
C7A—H7AA⋯O2Biv	0.93	2.42	3.217 (3)	144
C8A—H8AA⋯O2Wv	0.93	2.50	3.339 (3)	151

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