Gabapentinium picrate.

The title compound {systematic name: [1-(carboxy-meth-yl)cyclo-hexyl]methanaminium 2,4,6-trinitro-phenolate}, C(9)H(18)NO(2) (+)·C(6)H(2)N(3)O(7) (-), was synthesized from picric acid and gabapentin. The crystal packing is stabilized by intra-molecular N-H⋯O=N and N-H⋯O-Ph hydrogen bonds. An O-H⋯O inter-action is also present.

Related literature

For background, see: Bryans & Wustrow (1999 ▶). For related structures, see: Ibers (2001 ▶); Swamy et al. (2007 ▶) and references cited therein.

Experimental

Crystal data

C9H18NO2 +·C6H2N3O7 −

M = 400.35

Monoclinic,

a = 11.576 (2) Å

b = 7.7312 (16) Å

c = 19.973 (4) Å

β = 91.425 (2)°

V = 1787.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.25 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.970, T max = 0.976

8899 measured reflections

3150 independent reflections

2408 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.182

S = 1.07

3150 reflections

256 parameters

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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/S1600536809008952/cs2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008952/cs2105Isup2.hkl

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

C9H18NO2+·C6H2N3O7−	F(000) = 840
Mr = 400.35	Dx = 1.488 Mg m−3
Monoclinic, P21/n	Melting point = 431–434 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.576 (2) Å	Cell parameters from 2666 reflections
b = 7.7312 (16) Å	θ = 2.8–25.1°
c = 19.973 (4) Å	µ = 0.12 mm−1
β = 91.425 (2)°	T = 296 K
V = 1787.0 (6) Å3	Block, yellow
Z = 4	0.25 × 0.25 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3150 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→13
Tmin = 0.970, Tmax = 0.976	k = −7→9
8899 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.083P)2 + 1.5949P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3150 reflections	Δρmax = 1.06 e Å−3
256 parameters	Δρmin = −0.55 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.075 (5)

	x	y	z	Uiso*/Ueq
C1	0.2919 (2)	0.3970 (4)	0.05392 (13)	0.0375 (6)
C2	0.3067 (2)	0.5162 (3)	0.10930 (13)	0.0362 (6)
C3	0.3639 (2)	0.6728 (3)	0.08832 (16)	0.0432 (7)
C4	0.3949 (2)	0.7066 (4)	0.02348 (17)	0.0499 (8)
H4	0.4323	0.8093	0.0131	0.060*
C5	0.3701 (2)	0.5869 (4)	−0.02563 (15)	0.0466 (8)
C6	0.3199 (2)	0.4315 (4)	−0.01060 (14)	0.0433 (7)
H6	0.3052	0.3503	−0.0441	0.052*
C7	0.4810 (2)	0.6530 (3)	0.67642 (12)	0.0328 (6)
C8	0.5192 (2)	0.4847 (3)	0.71209 (13)	0.0372 (6)
H8A	0.6030	0.4811	0.7144	0.045*
H8B	0.4920	0.4871	0.7576	0.045*
C9	0.4752 (3)	0.3205 (4)	0.67810 (17)	0.0521 (8)
H9A	0.5112	0.3084	0.6350	0.063*
H9B	0.4972	0.2213	0.7053	0.063*
C10	0.3458 (3)	0.3223 (5)	0.6679 (2)	0.0727 (11)
H10A	0.3093	0.3214	0.7111	0.087*
H10B	0.3216	0.2192	0.6437	0.087*
C11	0.3074 (3)	0.4818 (5)	0.6289 (2)	0.0664 (10)
H11A	0.2237	0.4833	0.6247	0.080*
H11B	0.3381	0.4771	0.5842	0.080*
C12	0.3490 (3)	0.6467 (4)	0.66370 (16)	0.0502 (8)
H12A	0.3109	0.6569	0.7062	0.060*
H12B	0.3261	0.7453	0.6364	0.060*
C13	0.5043 (3)	0.8069 (4)	0.72276 (14)	0.0429 (7)
H13A	0.4866	0.9122	0.6982	0.051*
H13B	0.4517	0.8003	0.7597	0.051*
C14	0.5472 (2)	0.6665 (3)	0.61064 (12)	0.0354 (6)
H14A	0.6290	0.6669	0.6222	0.042*
H14B	0.5319	0.5615	0.5853	0.042*
C15	0.5244 (2)	0.8160 (3)	0.56474 (13)	0.0365 (6)
N1	0.2450 (3)	0.2259 (3)	0.06681 (13)	0.0530 (7)
N2	0.3944 (3)	0.8022 (3)	0.13862 (17)	0.0582 (8)
N3	0.4040 (2)	0.6182 (5)	−0.09448 (17)	0.0633 (9)
N4	0.6251 (2)	0.8199 (3)	0.75081 (12)	0.0490 (7)
H4A	0.6443	0.7210	0.7710	0.074*
H4B	0.6292	0.9060	0.7803	0.074*
H4C	0.6734	0.8404	0.7178	0.074*
O1	0.1815 (4)	0.1631 (5)	0.02309 (16)	0.1380 (18)
O2	0.2579 (2)	0.1585 (3)	0.11974 (12)	0.0681 (8)
O3	0.2754 (2)	0.4861 (3)	0.16754 (10)	0.0492 (6)
O4	0.3311 (2)	0.8242 (3)	0.18624 (13)	0.0638 (7)
O5	0.4804 (3)	0.8876 (4)	0.1315 (2)	0.1066 (12)
O6	0.4584 (2)	0.7510 (5)	−0.10551 (16)	0.0911 (10)
O7	0.3773 (3)	0.5105 (5)	−0.13704 (14)	0.0893 (10)
O8	0.4688 (2)	0.9447 (3)	0.57786 (10)	0.0609 (7)
O9	0.5759 (2)	0.7959 (3)	0.50733 (11)	0.0616 (7)
H9	0.5576	0.8754	0.4820	0.092*

	U11	U22	U33	U12	U13	U23
C1	0.0436 (15)	0.0344 (14)	0.0344 (14)	−0.0022 (12)	−0.0046 (11)	0.0041 (11)
C2	0.0400 (14)	0.0318 (14)	0.0364 (15)	0.0020 (11)	−0.0054 (11)	0.0019 (11)
C3	0.0420 (15)	0.0297 (14)	0.0575 (18)	−0.0008 (12)	−0.0075 (13)	0.0030 (13)
C4	0.0384 (16)	0.0382 (16)	0.073 (2)	0.0036 (13)	0.0079 (14)	0.0239 (16)
C5	0.0394 (15)	0.0549 (19)	0.0457 (16)	0.0112 (14)	0.0059 (12)	0.0156 (15)
C6	0.0428 (16)	0.0514 (18)	0.0356 (15)	0.0031 (13)	−0.0026 (12)	0.0021 (13)
C7	0.0415 (14)	0.0297 (13)	0.0271 (13)	0.0035 (11)	0.0006 (10)	0.0015 (10)
C8	0.0490 (16)	0.0323 (14)	0.0301 (14)	−0.0001 (12)	−0.0014 (11)	0.0044 (11)
C9	0.073 (2)	0.0313 (16)	0.0520 (18)	−0.0097 (15)	−0.0040 (15)	0.0041 (13)
C10	0.076 (3)	0.058 (2)	0.084 (3)	−0.031 (2)	0.002 (2)	0.004 (2)
C11	0.0460 (19)	0.078 (3)	0.074 (2)	−0.0127 (18)	−0.0084 (16)	−0.001 (2)
C12	0.0416 (16)	0.059 (2)	0.0505 (18)	0.0065 (14)	0.0054 (13)	0.0072 (15)
C13	0.0624 (19)	0.0337 (15)	0.0325 (14)	0.0073 (13)	0.0012 (13)	−0.0009 (11)
C14	0.0466 (15)	0.0311 (14)	0.0285 (13)	0.0016 (11)	0.0016 (11)	0.0015 (10)
C15	0.0480 (16)	0.0346 (15)	0.0268 (13)	−0.0010 (12)	−0.0009 (11)	0.0005 (11)
N1	0.0781 (19)	0.0435 (15)	0.0369 (14)	−0.0202 (13)	−0.0054 (12)	−0.0054 (12)
N2	0.0603 (17)	0.0320 (14)	0.082 (2)	−0.0054 (13)	−0.0139 (16)	−0.0025 (14)
N3	0.0510 (16)	0.078 (2)	0.0612 (19)	0.0195 (16)	0.0141 (14)	0.0320 (18)
N4	0.0808 (19)	0.0321 (13)	0.0337 (13)	−0.0104 (12)	−0.0085 (12)	−0.0038 (10)
O1	0.240 (5)	0.111 (3)	0.0613 (19)	−0.105 (3)	−0.031 (2)	0.0042 (18)
O2	0.0992 (19)	0.0492 (14)	0.0547 (15)	−0.0240 (13)	−0.0203 (13)	0.0170 (11)
O3	0.0769 (15)	0.0367 (11)	0.0340 (11)	−0.0009 (10)	0.0009 (10)	0.0000 (8)
O4	0.0849 (18)	0.0401 (13)	0.0655 (16)	0.0009 (12)	−0.0174 (14)	−0.0124 (11)
O5	0.089 (2)	0.072 (2)	0.159 (3)	−0.0438 (18)	0.005 (2)	−0.029 (2)
O6	0.0774 (19)	0.101 (2)	0.096 (2)	0.0071 (17)	0.0278 (16)	0.0562 (19)
O7	0.106 (2)	0.116 (3)	0.0471 (15)	0.016 (2)	0.0227 (15)	0.0115 (17)
O8	0.1037 (19)	0.0422 (13)	0.0375 (12)	0.0242 (13)	0.0137 (11)	0.0090 (10)
O9	0.0925 (18)	0.0544 (14)	0.0389 (12)	0.0224 (13)	0.0198 (11)	0.0148 (10)

C1—C6	1.363 (4)	C10—H10B	0.9700
C1—C2	1.447 (4)	C11—C12	1.524 (5)
C1—N1	1.455 (4)	C11—H11A	0.9700
C2—O3	1.249 (3)	C11—H11B	0.9700
C2—C3	1.447 (4)	C12—H12A	0.9700
C3—C4	1.377 (4)	C12—H12B	0.9700
C3—N2	1.455 (4)	C13—N4	1.497 (4)
C4—C5	1.374 (5)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.371 (4)	C14—C15	1.495 (4)
C5—N3	1.460 (4)	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—C13	1.527 (4)	C15—O8	1.217 (3)
C7—C14	1.541 (3)	C15—O9	1.314 (3)
C7—C8	1.543 (3)	N1—O2	1.185 (3)
C7—C12	1.544 (4)	N1—O1	1.228 (4)
C8—C9	1.522 (4)	N2—O5	1.205 (4)
C8—H8A	0.9700	N2—O4	1.227 (4)
C8—H8B	0.9700	N3—O7	1.225 (4)
C9—C10	1.506 (5)	N3—O6	1.227 (4)
C9—H9A	0.9700	N4—H4A	0.8900
C9—H9B	0.9700	N4—H4B	0.8900
C10—C11	1.520 (5)	N4—H4C	0.8900
C10—H10A	0.9700	O9—H9	0.8200
C6—C1—C2	124.9 (3)	C10—C11—H11A	109.4
C6—C1—N1	116.3 (3)	C12—C11—H11A	109.4
C2—C1—N1	118.8 (2)	C10—C11—H11B	109.4
O3—C2—C1	124.2 (2)	C12—C11—H11B	109.4
O3—C2—C3	124.8 (3)	H11A—C11—H11B	108.0
C1—C2—C3	111.0 (2)	C11—C12—C7	113.7 (3)
C4—C3—C2	124.2 (3)	C11—C12—H12A	108.8
C4—C3—N2	117.0 (3)	C7—C12—H12A	108.8
C2—C3—N2	118.7 (3)	C11—C12—H12B	108.8
C5—C4—C3	119.3 (3)	C7—C12—H12B	108.8
C5—C4—H4	120.4	H12A—C12—H12B	107.7
C3—C4—H4	120.4	N4—C13—C7	115.4 (2)
C6—C5—C4	121.1 (3)	N4—C13—H13A	108.4
C6—C5—N3	118.5 (3)	C7—C13—H13A	108.4
C4—C5—N3	120.3 (3)	N4—C13—H13B	108.4
C1—C6—C5	119.4 (3)	C7—C13—H13B	108.4
C1—C6—H6	120.3	H13A—C13—H13B	107.5
C5—C6—H6	120.3	C15—C14—C7	119.4 (2)
C13—C7—C14	112.4 (2)	C15—C14—H14A	107.5
C13—C7—C8	109.4 (2)	C7—C14—H14A	107.5
C14—C7—C8	107.9 (2)	C15—C14—H14B	107.5
C13—C7—C12	106.5 (2)	C7—C14—H14B	107.5
C14—C7—C12	111.9 (2)	H14A—C14—H14B	107.0
C8—C7—C12	108.7 (2)	O8—C15—O9	122.6 (2)
C9—C8—C7	114.1 (2)	O8—C15—C14	125.9 (2)
C9—C8—H8A	108.7	O9—C15—C14	111.5 (2)
C7—C8—H8A	108.7	O2—N1—O1	121.3 (3)
C9—C8—H8B	108.7	O2—N1—C1	121.2 (2)
C7—C8—H8B	108.7	O1—N1—C1	117.0 (3)
H8A—C8—H8B	107.6	O5—N2—O4	121.8 (3)
C10—C9—C8	111.9 (3)	O5—N2—C3	118.9 (3)
C10—C9—H9A	109.2	O4—N2—C3	119.4 (3)
C8—C9—H9A	109.2	O7—N3—O6	124.5 (3)
C10—C9—H9B	109.2	O7—N3—C5	118.1 (3)
C8—C9—H9B	109.2	O6—N3—C5	117.3 (4)
H9A—C9—H9B	107.9	C13—N4—H4A	109.5
C9—C10—C11	110.7 (3)	C13—N4—H4B	109.5
C9—C10—H10A	109.5	H4A—N4—H4B	109.5
C11—C10—H10A	109.5	C13—N4—H4C	109.5
C9—C10—H10B	109.5	H4A—N4—H4C	109.5
C11—C10—H10B	109.5	H4B—N4—H4C	109.5
H10A—C10—H10B	108.1	C15—O9—H9	109.5
C10—C11—C12	111.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O8i	0.82	1.86	2.672 (3)	174
N4—H4C···O4ii	0.89	2.32	2.957 (4)	128
N4—H4C···O3ii	0.89	2.06	2.862 (3)	149
N4—H4B···O2iii	0.89	2.41	2.894 (3)	114
N4—H4B···O4i	0.89	2.23	3.063 (3)	155
N4—H4A···O3iii	0.89	2.21	3.081 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O8i	0.82	1.86	2.672 (3)	174
N4—H4C⋯O4ii	0.89	2.32	2.957 (4)	128
N4—H4C⋯O3ii	0.89	2.06	2.862 (3)	149
N4—H4B⋯O2iii	0.89	2.41	2.894 (3)	114
N4—H4B⋯O4i	0.89	2.23	3.063 (3)	155
N4—H4A⋯O3iii	0.89	2.21	3.081 (3)	166

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