4-[(E)-(2,4-Difluoro-phen-yl)(hydroxy-imino)meth-yl]piperidinium picrate.

The title compound, C(12)H(15)F(2)N(2)O(+)·C(6)H(2)N(3)O(7) (-), a picrate salt of 4-[(E)-(2,4-difluoro-phen-yl)(hydroxy-imino)meth-yl]piper-idine, crystallizes with two independent mol-ecules in a cation-anion pair in the asymmetric unit. In the cation, a methyl group is tris-ubstituted by hydroxy-imino, piperidin-4-yl and 2,4-difluoro-phenyl groups, the latter of which contains an F atom disordered over two positions in the ring [occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydr-oxy group is in a synclinical conformation nearly orthogonal [N-C-C-C = 72.44 (19)°] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4-difluoro-phenyl and piperidin-4-yl groups is 60.2 (3)°. In the picrate anion, the mean planes of the two o-NO(2) and single p-NO(2) groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxy-imino, piperidin-4-yl and 2,4-difluoro-phenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)°, respectively. Extensive hydrogen-bond inter-actions occur between the cation-anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO(2) O atoms of the picrate anion at different positions in the unit cell, which form separate N-H⋯(O,O) bifurcated inter-molecular hydrogen-bond inter-actions. Also, the hydr-oxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011).

Related literature

(Z)-(2,4-Difluoro­phen­yl)(piperidin-4-yl)methanone oxime is an inter­mediate in the preparation of risperidone, an anti­psychotic used to treat schizophrenia, see: Umbricht & Kane, (1995 ▶). For related structures, see: Hu et al. (2008 ▶); Jottier et al. (1992 ▶); Naveen et al. (2007 ▶); Ravikumar & Sridhar (2006 ▶); Yathirajan et al. (2005 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶) and for Mogul, see: Bruno et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H15F2N2O+·C6H2N3O7 −

M = 469.37

Monoclinic,

a = 6.0926 (4) Å

b = 13.5364 (8) Å

c = 24.0417 (14) Å

β = 92.671 (6)°

V = 1980.63 (19) Å3

Z = 4

Cu Kα radiation

μ = 1.20 mm−1

T = 110 K

0.49 × 0.45 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.733, T max = 1.000

7628 measured reflections

3910 independent reflections

3475 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.05

3910 reflections

303 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035363/zq2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035363/zq2003Isup2.hkl

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

C12H15F2N2O+·C6H2N3O7−	F(000) = 968
Mr = 469.37	Dx = 1.574 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 4482 reflections
a = 6.0926 (4) Å	θ = 4.9–74.1°
b = 13.5364 (8) Å	µ = 1.20 mm−1
c = 24.0417 (14) Å	T = 110 K
β = 92.671 (6)°	Chunk, pale yellow
V = 1980.63 (19) Å3	0.49 × 0.45 × 0.38 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	3910 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3475 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 10.5081 pixels mm-1	θmax = 74.1°, θmin = 4.9°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→16
Tmin = 0.734, Tmax = 1.000	l = −29→29
7628 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0619P)2 + 1.0569P] where P = (Fo2 + 2Fc2)/3
3910 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) 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.

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	Occ. (<1)
F1A	0.4117 (3)	0.58470 (13)	0.70084 (6)	0.0326 (4)	0.631 (4)
F1B	−0.0826 (5)	0.4942 (2)	0.55863 (11)	0.0326 (4)	0.37
F2	−0.2362 (2)	0.41781 (9)	0.74432 (5)	0.0519 (4)
O1	0.3558 (2)	0.44002 (9)	0.54602 (6)	0.0389 (3)
H1A	0.4171	0.4159	0.5185	0.058*
N1	0.3999 (3)	0.54236 (11)	0.54919 (6)	0.0309 (3)
N2	0.5153 (2)	0.88427 (9)	0.55578 (5)	0.0199 (3)
H2A	0.5653	0.8665	0.5217	0.024*
H2B	0.5390	0.9509	0.5604	0.024*
C1	0.1660 (3)	0.53694 (11)	0.62919 (6)	0.0214 (3)
C2	0.2218 (3)	0.53902 (12)	0.68601 (7)	0.0249 (3)
H2	0.3559	0.5695	0.6982	0.030*	0.369 (4)
C3	0.0908 (3)	0.49879 (12)	0.72519 (7)	0.0299 (4)
H3A	0.1331	0.4999	0.7637	0.036*
C4	−0.1038 (3)	0.45693 (13)	0.70620 (8)	0.0332 (4)
C5	−0.1698 (3)	0.45176 (13)	0.65070 (8)	0.0321 (4)
H5A	−0.3052	0.4218	0.6390	0.039*
C6	−0.0313 (3)	0.49188 (12)	0.61243 (7)	0.0261 (3)
H6	−0.0723	0.4885	0.5739	0.031*	0.631 (4)
C7	0.3115 (3)	0.58538 (12)	0.58942 (6)	0.0221 (3)
C8	0.3575 (2)	0.69523 (11)	0.59583 (6)	0.0206 (3)
H8A	0.3034	0.7169	0.6325	0.025*
C9	0.2332 (3)	0.75380 (13)	0.55000 (7)	0.0273 (4)
H9A	0.2810	0.7318	0.5132	0.033*
H9B	0.0738	0.7405	0.5516	0.033*
C10	0.2742 (3)	0.86397 (13)	0.55644 (8)	0.0286 (4)
H10A	0.1964	0.9001	0.5256	0.034*
H10B	0.2167	0.8873	0.5920	0.034*
C11	0.6425 (3)	0.82942 (11)	0.60045 (7)	0.0237 (3)
H11A	0.5979	0.8524	0.6374	0.028*
H11B	0.8012	0.8432	0.5977	0.028*
C12	0.6024 (3)	0.71882 (11)	0.59519 (7)	0.0230 (3)
H12A	0.6812	0.6842	0.6264	0.028*
H12B	0.6612	0.6947	0.5600	0.028*
O1B	0.48994 (19)	0.91121 (8)	0.44016 (5)	0.0257 (3)
O21B	0.7803 (2)	0.77495 (10)	0.47615 (5)	0.0327 (3)
O22B	1.01401 (18)	0.74502 (9)	0.41357 (5)	0.0262 (3)
O41B	0.7531 (3)	0.69201 (10)	0.22667 (5)	0.0441 (4)
O42B	0.4368 (3)	0.74855 (11)	0.19724 (5)	0.0426 (4)
O61B	−0.0029 (2)	0.93104 (14)	0.31606 (7)	0.0563 (5)
O62B	0.1039 (2)	0.97294 (11)	0.39934 (8)	0.0495 (4)
N2B	0.8313 (2)	0.77022 (10)	0.42725 (5)	0.0207 (3)
N4B	0.5790 (3)	0.73383 (11)	0.23427 (6)	0.0322 (4)
N6B	0.1329 (2)	0.93020 (11)	0.35541 (7)	0.0327 (4)
C1B	0.4929 (2)	0.86302 (11)	0.39577 (6)	0.0197 (3)
C2B	0.6651 (2)	0.79351 (11)	0.38377 (6)	0.0191 (3)
C3B	0.6944 (3)	0.75188 (11)	0.33251 (6)	0.0219 (3)
H3BA	0.8174	0.7107	0.3266	0.026*
C4B	0.5401 (3)	0.77135 (12)	0.28969 (6)	0.0249 (3)
C5B	0.3567 (3)	0.82860 (12)	0.29821 (7)	0.0268 (4)
H5BA	0.2481	0.8377	0.2690	0.032*
C6B	0.3327 (3)	0.87222 (11)	0.34922 (7)	0.0241 (3)

	U11	U22	U33	U12	U13	U23
F1A	0.0361 (8)	0.0377 (8)	0.0237 (7)	−0.0054 (6)	−0.0035 (5)	−0.0009 (6)
F1B	0.0361 (8)	0.0377 (8)	0.0237 (7)	−0.0054 (6)	−0.0035 (5)	−0.0009 (6)
F2	0.0645 (8)	0.0379 (6)	0.0566 (8)	−0.0099 (6)	0.0386 (6)	0.0049 (5)
O1	0.0580 (8)	0.0199 (6)	0.0410 (7)	−0.0143 (6)	0.0276 (6)	−0.0133 (5)
N1	0.0441 (8)	0.0187 (7)	0.0313 (7)	−0.0118 (6)	0.0156 (6)	−0.0087 (6)
N2	0.0251 (6)	0.0157 (6)	0.0189 (6)	0.0022 (5)	0.0021 (5)	0.0010 (5)
C1	0.0263 (8)	0.0147 (7)	0.0235 (8)	0.0008 (6)	0.0064 (6)	−0.0009 (6)
C2	0.0305 (8)	0.0187 (7)	0.0259 (8)	0.0016 (6)	0.0055 (6)	−0.0020 (6)
C3	0.0466 (10)	0.0196 (8)	0.0243 (8)	0.0054 (7)	0.0104 (7)	0.0013 (6)
C4	0.0428 (10)	0.0196 (8)	0.0390 (10)	0.0010 (7)	0.0229 (8)	0.0028 (7)
C5	0.0254 (8)	0.0229 (8)	0.0488 (11)	−0.0027 (7)	0.0106 (7)	−0.0037 (7)
C6	0.0282 (8)	0.0209 (8)	0.0293 (8)	0.0014 (6)	0.0040 (7)	−0.0026 (6)
C7	0.0259 (7)	0.0205 (8)	0.0203 (7)	−0.0040 (6)	0.0032 (6)	−0.0024 (6)
C8	0.0265 (8)	0.0183 (7)	0.0175 (7)	−0.0021 (6)	0.0050 (6)	−0.0023 (6)
C9	0.0177 (7)	0.0291 (9)	0.0347 (9)	0.0012 (6)	−0.0053 (6)	−0.0001 (7)
C10	0.0221 (8)	0.0257 (8)	0.0378 (9)	0.0083 (6)	0.0004 (7)	0.0045 (7)
C11	0.0259 (8)	0.0185 (7)	0.0259 (8)	−0.0014 (6)	−0.0080 (6)	0.0022 (6)
C12	0.0238 (8)	0.0164 (7)	0.0277 (8)	−0.0002 (6)	−0.0077 (6)	0.0025 (6)
O1B	0.0371 (6)	0.0189 (5)	0.0212 (5)	0.0061 (5)	0.0042 (5)	0.0021 (4)
O21B	0.0333 (6)	0.0485 (8)	0.0163 (5)	0.0145 (6)	0.0005 (5)	−0.0001 (5)
O22B	0.0217 (5)	0.0304 (6)	0.0266 (6)	0.0043 (5)	0.0024 (4)	−0.0007 (5)
O41B	0.0744 (10)	0.0356 (7)	0.0227 (6)	0.0128 (7)	0.0063 (6)	−0.0007 (5)
O42B	0.0634 (9)	0.0424 (8)	0.0206 (6)	−0.0175 (7)	−0.0141 (6)	0.0038 (5)
O61B	0.0276 (7)	0.0832 (12)	0.0574 (9)	0.0107 (7)	−0.0072 (6)	0.0273 (9)
O62B	0.0328 (7)	0.0341 (8)	0.0810 (11)	0.0108 (6)	−0.0029 (7)	−0.0201 (8)
N2B	0.0226 (6)	0.0205 (6)	0.0189 (6)	0.0015 (5)	0.0000 (5)	−0.0005 (5)
N4B	0.0563 (10)	0.0218 (7)	0.0179 (7)	−0.0109 (7)	−0.0037 (6)	0.0033 (5)
N6B	0.0222 (7)	0.0233 (7)	0.0525 (10)	−0.0023 (6)	−0.0006 (6)	0.0156 (7)
C1B	0.0239 (7)	0.0154 (7)	0.0202 (7)	−0.0029 (6)	0.0028 (6)	0.0041 (5)
C2B	0.0213 (7)	0.0175 (7)	0.0183 (7)	−0.0028 (6)	−0.0002 (5)	0.0029 (6)
C3B	0.0289 (8)	0.0169 (7)	0.0199 (7)	−0.0026 (6)	0.0015 (6)	0.0008 (6)
C4B	0.0373 (9)	0.0192 (7)	0.0180 (7)	−0.0076 (7)	−0.0019 (6)	0.0020 (6)
C5B	0.0300 (8)	0.0243 (8)	0.0253 (8)	−0.0098 (6)	−0.0086 (6)	0.0092 (6)
C6B	0.0216 (7)	0.0188 (7)	0.0318 (8)	−0.0019 (6)	−0.0007 (6)	0.0081 (6)

F2—C4	1.3563 (19)	C10—H10A	0.9900
O1—N1	1.4126 (18)	C10—H10B	0.9900
O1—H1A	0.8400	C11—C12	1.521 (2)
N1—C7	1.270 (2)	C11—H11A	0.9900
N2—C11	1.4926 (19)	C11—H11B	0.9900
N2—C10	1.495 (2)	C12—H12A	0.9900
N2—H2A	0.9200	C12—H12B	0.9900
N2—H2B	0.9200	O1B—C1B	1.2517 (19)
C1—C6	1.391 (2)	O21B—N2B	1.2317 (17)
C1—C2	1.393 (2)	O22B—N2B	1.2240 (17)
C1—C7	1.486 (2)	O41B—N4B	1.224 (2)
C2—C3	1.375 (2)	O42B—N4B	1.229 (2)
C2—H2	0.9500	O61B—N6B	1.227 (2)
C3—C4	1.373 (3)	O62B—N6B	1.224 (2)
C3—H3A	0.9500	N2B—C2B	1.4556 (19)
C4—C5	1.377 (3)	N4B—C4B	1.456 (2)
C5—C6	1.388 (2)	N6B—C6B	1.462 (2)
C5—H5A	0.9500	C1B—C2B	1.448 (2)
C6—H6	0.9500	C1B—C6B	1.456 (2)
C7—C8	1.520 (2)	C2B—C3B	1.374 (2)
C8—C12	1.526 (2)	C3B—C4B	1.387 (2)
C8—C9	1.529 (2)	C3B—H3BA	0.9500
C8—H8A	1.0000	C4B—C5B	1.383 (3)
C9—C10	1.519 (2)	C5B—C6B	1.375 (2)
C9—H9A	0.9900	C5B—H5BA	0.9500
C9—H9B	0.9900
N1—O1—H1A	109.5	C9—C10—H10A	109.7
C7—N1—O1	113.86 (13)	N2—C10—H10B	109.7
C11—N2—C10	112.24 (12)	C9—C10—H10B	109.7
C11—N2—H2A	109.2	H10A—C10—H10B	108.2
C10—N2—H2A	109.2	N2—C11—C12	110.71 (12)
C11—N2—H2B	109.2	N2—C11—H11A	109.5
C10—N2—H2B	109.2	C12—C11—H11A	109.5
H2A—N2—H2B	107.9	N2—C11—H11B	109.5
C6—C1—C2	117.46 (14)	C12—C11—H11B	109.5
C6—C1—C7	122.72 (14)	H11A—C11—H11B	108.1
C2—C1—C7	119.78 (14)	C11—C12—C8	111.00 (13)
C3—C2—C1	122.77 (16)	C11—C12—H12A	109.4
C3—C2—H2	118.6	C8—C12—H12A	109.4
C1—C2—H2	118.6	C11—C12—H12B	109.4
C4—C3—C2	117.09 (16)	C8—C12—H12B	109.4
C4—C3—H3A	121.5	H12A—C12—H12B	108.0
C2—C3—H3A	121.5	O22B—N2B—O21B	122.94 (13)
F2—C4—C3	117.88 (17)	O22B—N2B—C2B	118.59 (12)
F2—C4—C5	118.62 (17)	O21B—N2B—C2B	118.45 (13)
C3—C4—C5	123.49 (16)	O41B—N4B—O42B	123.60 (15)
C4—C5—C6	117.61 (16)	O41B—N4B—C4B	118.50 (14)
C4—C5—H5A	121.2	O42B—N4B—C4B	117.86 (17)
C6—C5—H5A	121.2	O62B—N6B—O61B	122.80 (16)
C5—C6—C1	121.57 (16)	O62B—N6B—C6B	119.71 (15)
C5—C6—H6	119.2	O61B—N6B—C6B	117.45 (17)
C1—C6—H6	119.2	O1B—C1B—C2B	123.23 (14)
N1—C7—C1	125.05 (14)	O1B—C1B—C6B	125.10 (14)
N1—C7—C8	116.31 (14)	C2B—C1B—C6B	111.61 (13)
C1—C7—C8	118.63 (13)	C3B—C2B—C1B	124.81 (14)
C7—C8—C12	112.30 (13)	C3B—C2B—N2B	116.10 (14)
C7—C8—C9	110.57 (13)	C1B—C2B—N2B	118.93 (13)
C12—C8—C9	109.62 (12)	C2B—C3B—C4B	118.41 (15)
C7—C8—H8A	108.1	C2B—C3B—H3BA	120.8
C12—C8—H8A	108.1	C4B—C3B—H3BA	120.8
C9—C8—H8A	108.1	C5B—C4B—C3B	121.40 (15)
C10—C9—C8	111.22 (13)	C5B—C4B—N4B	119.87 (15)
C10—C9—H9A	109.4	C3B—C4B—N4B	118.67 (16)
C8—C9—H9A	109.4	C6B—C5B—C4B	119.53 (15)
C10—C9—H9B	109.4	C6B—C5B—H5BA	120.2
C8—C9—H9B	109.4	C4B—C5B—H5BA	120.2
H9A—C9—H9B	108.0	C5B—C6B—C1B	123.61 (15)
N2—C10—C9	109.65 (13)	C5B—C6B—N6B	116.43 (15)
N2—C10—H10A	109.7	C1B—C6B—N6B	119.96 (15)
C6—C1—C2—C3	0.0 (2)	O1B—C1B—C2B—C3B	−168.56 (15)
C7—C1—C2—C3	177.62 (15)	C6B—C1B—C2B—C3B	9.0 (2)
C1—C2—C3—C4	−1.2 (2)	O1B—C1B—C2B—N2B	6.6 (2)
C2—C3—C4—F2	−179.33 (15)	C6B—C1B—C2B—N2B	−175.87 (12)
C2—C3—C4—C5	1.4 (3)	O22B—N2B—C2B—C3B	23.4 (2)
F2—C4—C5—C6	−179.72 (15)	O21B—N2B—C2B—C3B	−155.21 (14)
C3—C4—C5—C6	−0.5 (3)	O22B—N2B—C2B—C1B	−152.14 (14)
C4—C5—C6—C1	−0.8 (2)	O21B—N2B—C2B—C1B	29.2 (2)
C2—C1—C6—C5	1.0 (2)	C1B—C2B—C3B—C4B	−5.0 (2)
C7—C1—C6—C5	−176.53 (15)	N2B—C2B—C3B—C4B	179.71 (13)
O1—N1—C7—C1	−2.5 (3)	C2B—C3B—C4B—C5B	−2.0 (2)
O1—N1—C7—C8	178.61 (14)	C2B—C3B—C4B—N4B	175.31 (14)
C6—C1—C7—N1	−60.4 (2)	O41B—N4B—C4B—C5B	172.66 (15)
C2—C1—C7—N1	122.18 (19)	O42B—N4B—C4B—C5B	−5.3 (2)
C6—C1—C7—C8	118.49 (17)	O41B—N4B—C4B—C3B	−4.7 (2)
C2—C1—C7—C8	−59.0 (2)	O42B—N4B—C4B—C3B	177.34 (15)
N1—C7—C8—C12	−50.3 (2)	C3B—C4B—C5B—C6B	4.0 (2)
C1—C7—C8—C12	130.70 (15)	N4B—C4B—C5B—C6B	−173.31 (14)
N1—C7—C8—C9	72.44 (19)	C4B—C5B—C6B—C1B	0.9 (2)
C1—C7—C8—C9	−106.51 (16)	C4B—C5B—C6B—N6B	−178.96 (14)
C7—C8—C9—C10	178.97 (13)	O1B—C1B—C6B—C5B	170.67 (15)
C12—C8—C9—C10	−56.69 (17)	C2B—C1B—C6B—C5B	−6.8 (2)
C11—N2—C10—C9	−57.77 (17)	O1B—C1B—C6B—N6B	−9.5 (2)
C8—C9—C10—N2	57.41 (18)	C2B—C1B—C6B—N6B	173.04 (13)
C10—N2—C11—C12	57.29 (17)	O62B—N6B—C6B—C5B	−178.23 (15)
N2—C11—C12—C8	−55.84 (17)	O61B—N6B—C6B—C5B	3.9 (2)
C7—C8—C12—C11	178.80 (13)	O62B—N6B—C6B—C1B	1.9 (2)
C9—C8—C12—C11	55.48 (17)	O61B—N6B—C6B—C1B	−175.92 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.84	2.09	2.7980 (18)	141
N2—H2A···O1B	0.92	2.08	2.8005 (16)	134
N2—H2A···O21B	0.92	2.14	2.9580 (17)	148
N2—H2B···O1Bii	0.92	1.87	2.7705 (17)	164
N2—H2B···O62Bii	0.92	2.56	3.170 (2)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.84	2.09	2.7980 (18)	141
N2—H2A⋯O1B	0.92	2.08	2.8005 (16)	134
N2—H2A⋯O21B	0.92	2.14	2.9580 (17)	148
N2—H2B⋯O1Bii	0.92	1.87	2.7705 (17)	164
N2—H2B⋯O62Bii	0.92	2.56	3.170 (2)	125

Symmetry codes: (i) ; (ii) .