Desipraminium picrate

Swamy, M.T.; Ashok, M.A.; Yathirajan, H.S.; Narayana, B.; Bolte, M.

doi:10.1107/S1600536807062393

Desipraminium picrate

M. T. Swamy, M. A. Ashok, H. S. Yathirajan, B. Narayana and M. Bolte

In the title compound, C₁₈H₂₃N₂⁺·C₆H₂N₃O₇⁻, the seven-membered ring of the cation adopts a boat conformation and the two aromatic rings form a dihedral angle of 52.79 (6)°. The anions and cations are connected via N—H

O hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062393/pv2047sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062393/pv2047Isup2.hkl Contains datablock I

CCDC reference: 674687

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.044
wR factor = 0.125
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N31
PLAT432_ALERT_2_C Short Inter X...Y Contact  O32    ..  C4      ..       3.00 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Desipramine, 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepine, is a tricyclic antidepressant (TCA) that inhibits the reuptake of norepinephrine. It is an active metabolite of imipramine. Along with other tricyclics, it has found use in treating neuropathic pain (Eriksoo & Rohte, 1970). It is one of the most potent and selective medications in this respect (Ware, 1987). The effect of desipramine hydrochloride on peripheral sympathetic nerve activity is reported (Cohen et al., 1990). Desipramine hydrochloride is proposed as a new reagent for detection of microamounts of blood in urine (Ahmed et al., 2002).

In continuation of our work on picrates of some pharmaceutical compounds (Yathirajan et al., 2007) and in view of the importance of desipramine, the paper reports the crystal structure of the title compound.

Geometric parameters of the title compound, are in the usual ranges. The seven-membered ring of the cation adopts a boat conformation with puckering parameters: q₂ = 0.7942 (14) Å, q₃ = 0.3246 (15) Å, ϕ₂ = 142.88 (11)°, ϕ₃ = 238.4 (3)° (Cremer & Pople, 1975) and the dihedral angle between the two aromatic rings is 52.79 (6)°. The anions and the cations are connected via N—H···O hydrogen bonds.

Related literature top

For related literature, see: Ahmed et al. (2002); Cohen et al. (1990); Cremer & Pople (1975); Eriksoo & Rohte (1970); Ware (1987); Yathirajan et al. (2007).

Experimental top

Desipramine hydrochloride (3.03 g, 0.01 mol) was dissolved in 20 ml of water. Picric acid (2.29 g, 0.01 mol) was dissolved in 30 ml of water. Both the solutions were mixed and stirred for few minutes. The formed complex was filtered, dried and crystals were obtained by slow evaporation of the ethanolic solution (m. p.: 431–435 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. The hydrogen bonds are shown as dashed lines.

Desipraminium picrate top

Crystal data top

C₁₈H₂₃N₂⁺·C₆H₂N₃O₇⁻	F(000) = 2080
M_r = 495.49	D_x = 1.387 Mg m⁻³
Monoclinic, C2/c	Melting point = 431–435 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 31.3356 (17) Å	Cell parameters from 20595 reflections
b = 6.7952 (3) Å	θ = 2.6–27.1°
c = 24.3100 (13) Å	µ = 0.10 mm⁻¹
β = 113.542 (4)°	T = 173 K
V = 4745.5 (4) Å³	Plate, yellow
Z = 8	0.38 × 0.27 × 0.01 mm

Data collection top

Stoe IPDSII two-circle diffractometer	4268 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 26.9°, θ_min = 2.7°
ω scans	h = −39→39
20306 measured reflections	k = −7→8
5107 independent reflections	l = −30→30

Refinement top

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0724P)² + 2.222P] where P = (F_o² + 2F_c²)/3
5107 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₈H₂₃N₂⁺·C₆H₂N₃O₇⁻	V = 4745.5 (4) Å³
M_r = 495.49	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 31.3356 (17) Å	µ = 0.10 mm⁻¹
b = 6.7952 (3) Å	T = 173 K
c = 24.3100 (13) Å	0.38 × 0.27 × 0.01 mm
β = 113.542 (4)°

Data collection top

Stoe IPDSII two-circle diffractometer	4268 reflections with I > 2σ(I)
20306 measured reflections	R_int = 0.041
5107 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.51 e Å⁻³
5107 reflections	Δρ_min = −0.40 e Å⁻³
334 parameters

Special details top

Experimental. Mol. Formula: [C₁₈H₂₃N₂]⁺[C₆H₂N₃O₇]^-. Composition: Found (Calculated): C: 58.11 (58.18); H: 5.02 (5.09); N: 14.18 (14.13).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.19958 (4)	0.69793 (17)	0.33576 (5)	0.0274 (2)
C1	0.16257 (4)	0.8250 (2)	0.29473 (6)	0.0307 (3)
H1A	0.1661	0.8353	0.2561	0.037*
H1B	0.1659	0.9587	0.3121	0.037*
C2	0.11411 (4)	0.7457 (2)	0.28317 (6)	0.0306 (3)
H2A	0.1100	0.7406	0.3215	0.037*
H2B	0.0903	0.8362	0.2558	0.037*
C3	0.10693 (4)	0.5419 (2)	0.25562 (6)	0.0282 (3)
H3A	0.1116	0.5462	0.2177	0.034*
H3B	0.1302	0.4504	0.2834	0.034*
N2	0.05907 (4)	0.46825 (18)	0.24327 (5)	0.0279 (2)
H2C	0.0533 (6)	0.476 (3)	0.2768 (8)	0.039 (4)*
H2D	0.0378 (6)	0.546 (3)	0.2147 (8)	0.038 (4)*
C4	0.05117 (5)	0.2612 (2)	0.22127 (7)	0.0358 (3)
H4A	0.0552	0.2517	0.1834	0.054*
H4B	0.0195	0.2210	0.2148	0.054*
H4C	0.0736	0.1746	0.2512	0.054*
C11	0.24440 (4)	0.7099 (2)	0.33351 (5)	0.0270 (3)
C12	0.27825 (4)	0.5601 (2)	0.35688 (6)	0.0284 (3)
C13	0.32069 (5)	0.5830 (2)	0.35128 (7)	0.0365 (3)
H13	0.3438	0.4844	0.3677	0.044*
C14	0.33045 (5)	0.7425 (3)	0.32298 (8)	0.0428 (4)
H14	0.3596	0.7526	0.3197	0.051*
C15	0.29706 (5)	0.8871 (3)	0.29952 (7)	0.0410 (4)
H15	0.3030	0.9970	0.2795	0.049*
C16	0.25482 (5)	0.8717 (2)	0.30518 (6)	0.0333 (3)
H16	0.2324	0.9734	0.2895	0.040*
C17	0.27325 (5)	0.3698 (2)	0.38639 (6)	0.0323 (3)
H17A	0.2937	0.3779	0.4296	0.039*
H17B	0.2851	0.2612	0.3692	0.039*
C21	0.19701 (4)	0.6516 (2)	0.39189 (6)	0.0276 (3)
C22	0.20698 (4)	0.4590 (2)	0.41360 (6)	0.0297 (3)
C23	0.20271 (5)	0.4103 (2)	0.46694 (6)	0.0371 (3)
H23	0.2092	0.2797	0.4819	0.045*
C24	0.18910 (5)	0.5491 (3)	0.49853 (7)	0.0415 (4)
H24	0.1867	0.5141	0.5350	0.050*
C25	0.17903 (5)	0.7386 (3)	0.47653 (7)	0.0395 (3)
H25	0.1696	0.8342	0.4979	0.047*
C26	0.18265 (5)	0.7901 (2)	0.42310 (6)	0.0332 (3)
H26	0.1753	0.9202	0.4079	0.040*
C27	0.22439 (5)	0.3143 (2)	0.38077 (6)	0.0321 (3)
H27A	0.2029	0.3117	0.3379	0.039*
H27B	0.2250	0.1809	0.3975	0.039*
O31	0.03288 (3)	0.55588 (17)	0.33651 (4)	0.0368 (2)
O32	0.09643 (6)	0.2663 (2)	0.35570 (5)	0.0636 (4)
O33	0.10213 (8)	0.0736 (3)	0.42713 (9)	0.0966 (7)
O34	0.10268 (6)	0.3341 (2)	0.60773 (6)	0.0680 (4)
O35	0.05950 (5)	0.5845 (2)	0.60442 (5)	0.0610 (4)
O36	0.00360 (6)	0.9942 (2)	0.42802 (6)	0.0713 (5)
O37	−0.02365 (5)	0.8368 (2)	0.34441 (5)	0.0601 (4)
N31	0.09068 (5)	0.2297 (2)	0.40142 (6)	0.0425 (3)
N32	0.07745 (5)	0.4708 (2)	0.58073 (6)	0.0478 (4)
N33	0.00219 (5)	0.8483 (2)	0.39776 (6)	0.0432 (3)
C31	0.04474 (4)	0.5401 (2)	0.39216 (6)	0.0292 (3)
C32	0.07263 (5)	0.3815 (2)	0.42855 (6)	0.0321 (3)
C33	0.08277 (5)	0.3588 (2)	0.48851 (6)	0.0367 (3)
H33	0.1000	0.2479	0.5097	0.044*
C34	0.06763 (5)	0.4987 (3)	0.51768 (6)	0.0375 (3)
C35	0.04210 (5)	0.6613 (2)	0.48778 (7)	0.0381 (3)
H35	0.0325	0.7583	0.5087	0.046*
C36	0.03096 (5)	0.6790 (2)	0.42741 (6)	0.0338 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0255 (5)	0.0265 (6)	0.0293 (5)	−0.0007 (4)	0.0099 (4)	0.0052 (4)
C1	0.0287 (6)	0.0257 (7)	0.0332 (6)	−0.0006 (5)	0.0077 (5)	0.0038 (5)
C2	0.0266 (6)	0.0268 (7)	0.0343 (6)	0.0021 (5)	0.0078 (5)	−0.0008 (5)
C3	0.0243 (6)	0.0300 (7)	0.0304 (6)	−0.0008 (5)	0.0110 (5)	−0.0024 (5)
N2	0.0258 (5)	0.0297 (6)	0.0278 (5)	−0.0015 (4)	0.0103 (4)	−0.0019 (4)
C4	0.0409 (7)	0.0314 (7)	0.0380 (7)	−0.0079 (6)	0.0186 (6)	−0.0073 (6)
C11	0.0270 (6)	0.0265 (6)	0.0259 (6)	−0.0045 (5)	0.0089 (5)	−0.0014 (5)
C12	0.0287 (6)	0.0281 (7)	0.0279 (6)	−0.0029 (5)	0.0106 (5)	−0.0011 (5)
C13	0.0299 (7)	0.0395 (8)	0.0404 (7)	0.0013 (6)	0.0144 (6)	0.0037 (6)
C14	0.0327 (7)	0.0506 (10)	0.0499 (9)	−0.0043 (7)	0.0213 (7)	0.0064 (7)
C15	0.0392 (8)	0.0420 (9)	0.0448 (8)	−0.0076 (7)	0.0200 (6)	0.0090 (7)
C16	0.0330 (7)	0.0309 (7)	0.0347 (7)	−0.0029 (6)	0.0122 (5)	0.0045 (6)
C17	0.0321 (6)	0.0266 (7)	0.0381 (7)	0.0024 (5)	0.0139 (5)	0.0039 (5)
C21	0.0227 (6)	0.0303 (7)	0.0280 (6)	−0.0043 (5)	0.0084 (5)	0.0010 (5)
C22	0.0226 (6)	0.0319 (7)	0.0325 (6)	−0.0031 (5)	0.0087 (5)	0.0049 (5)
C23	0.0283 (6)	0.0448 (9)	0.0372 (7)	0.0023 (6)	0.0119 (6)	0.0138 (6)
C24	0.0318 (7)	0.0612 (11)	0.0322 (7)	0.0024 (7)	0.0136 (6)	0.0102 (7)
C25	0.0335 (7)	0.0504 (9)	0.0357 (7)	−0.0005 (6)	0.0151 (6)	−0.0050 (6)
C26	0.0299 (6)	0.0322 (7)	0.0372 (7)	−0.0026 (5)	0.0130 (5)	−0.0012 (6)
C27	0.0320 (7)	0.0256 (7)	0.0365 (7)	−0.0031 (5)	0.0112 (5)	0.0039 (5)
O31	0.0328 (5)	0.0484 (6)	0.0290 (5)	0.0081 (4)	0.0121 (4)	0.0044 (4)
O32	0.0868 (10)	0.0726 (10)	0.0390 (6)	0.0363 (8)	0.0332 (7)	0.0103 (6)
O33	0.1541 (18)	0.0715 (11)	0.1071 (13)	0.0735 (12)	0.0972 (14)	0.0479 (10)
O34	0.0879 (10)	0.0748 (10)	0.0363 (6)	0.0239 (8)	0.0193 (6)	0.0147 (6)
O35	0.0617 (8)	0.0845 (10)	0.0341 (6)	0.0097 (7)	0.0164 (6)	−0.0104 (6)
O36	0.0940 (11)	0.0473 (8)	0.0601 (8)	0.0245 (8)	0.0176 (8)	−0.0128 (7)
O37	0.0706 (8)	0.0502 (8)	0.0416 (6)	0.0220 (6)	0.0035 (6)	0.0007 (5)
N31	0.0410 (7)	0.0471 (8)	0.0428 (7)	0.0167 (6)	0.0203 (6)	0.0095 (6)
N32	0.0470 (8)	0.0627 (10)	0.0300 (6)	0.0009 (7)	0.0114 (6)	−0.0016 (6)
N33	0.0478 (7)	0.0355 (7)	0.0412 (7)	0.0072 (6)	0.0126 (6)	−0.0023 (6)
C31	0.0231 (6)	0.0332 (7)	0.0300 (6)	−0.0017 (5)	0.0094 (5)	−0.0002 (5)
C32	0.0279 (6)	0.0374 (8)	0.0320 (6)	0.0029 (5)	0.0128 (5)	0.0008 (6)
C33	0.0305 (7)	0.0436 (8)	0.0339 (7)	0.0040 (6)	0.0105 (5)	0.0076 (6)
C34	0.0342 (7)	0.0481 (9)	0.0272 (6)	−0.0012 (6)	0.0091 (5)	−0.0009 (6)
C35	0.0360 (7)	0.0415 (8)	0.0334 (7)	−0.0014 (6)	0.0104 (6)	−0.0084 (6)
C36	0.0314 (7)	0.0319 (7)	0.0337 (7)	0.0012 (5)	0.0084 (5)	−0.0016 (6)

Geometric parameters (Å, º) top

N1—C11	1.4297 (16)	C21—C26	1.392 (2)
N1—C21	1.4335 (17)	C21—C22	1.399 (2)
N1—C1	1.4699 (16)	C22—C23	1.3955 (19)
C1—C2	1.5279 (18)	C22—C27	1.500 (2)
C1—H1A	0.9900	C23—C24	1.386 (2)
C1—H1B	0.9900	C23—H23	0.9500
C2—C3	1.5156 (19)	C24—C25	1.382 (2)
C2—H2A	0.9900	C24—H24	0.9500
C2—H2B	0.9900	C25—C26	1.393 (2)
C3—N2	1.4933 (16)	C25—H25	0.9500
C3—H3A	0.9900	C26—H26	0.9500
C3—H3B	0.9900	C27—H27A	0.9900
N2—C4	1.4906 (18)	C27—H27B	0.9900
N2—H2C	0.904 (19)	O31—C31	1.2564 (16)
N2—H2D	0.915 (19)	O32—N31	1.2203 (18)
C4—H4A	0.9800	O33—N31	1.211 (2)
C4—H4B	0.9800	O34—N32	1.227 (2)
C4—H4C	0.9800	O35—N32	1.226 (2)
C11—C16	1.4038 (19)	O36—N33	1.2245 (19)
C11—C12	1.4146 (19)	O37—N33	1.2267 (18)
C12—C13	1.3986 (19)	N31—C32	1.455 (2)
C12—C17	1.5171 (19)	N32—C34	1.4504 (19)
C13—C14	1.382 (2)	N33—C36	1.462 (2)
C13—H13	0.9500	C31—C32	1.446 (2)
C14—C15	1.381 (2)	C31—C36	1.452 (2)
C14—H14	0.9500	C32—C33	1.371 (2)
C15—C16	1.388 (2)	C33—C34	1.379 (2)
C15—H15	0.9500	C33—H33	0.9500
C16—H16	0.9500	C34—C35	1.387 (2)
C17—C27	1.5292 (19)	C35—C36	1.371 (2)
C17—H17A	0.9900	C35—H35	0.9500
C17—H17B	0.9900

C11—N1—C21	118.58 (10)	C12—C17—H17B	108.0
C11—N1—C1	117.48 (10)	C27—C17—H17B	108.0
C21—N1—C1	116.48 (11)	H17A—C17—H17B	107.2
N1—C1—C2	112.00 (11)	C26—C21—C22	119.94 (13)
N1—C1—H1A	109.2	C26—C21—N1	121.60 (12)
C2—C1—H1A	109.2	C22—C21—N1	118.38 (12)
N1—C1—H1B	109.2	C23—C22—C21	118.83 (14)
C2—C1—H1B	109.2	C23—C22—C27	121.97 (13)
H1A—C1—H1B	107.9	C21—C22—C27	119.12 (12)
C3—C2—C1	111.37 (11)	C24—C23—C22	121.23 (15)
C3—C2—H2A	109.4	C24—C23—H23	119.4
C1—C2—H2A	109.4	C22—C23—H23	119.4
C3—C2—H2B	109.4	C25—C24—C23	119.52 (14)
C1—C2—H2B	109.4	C25—C24—H24	120.2
H2A—C2—H2B	108.0	C23—C24—H24	120.2
N2—C3—C2	110.79 (11)	C24—C25—C26	120.26 (15)
N2—C3—H3A	109.5	C24—C25—H25	119.9
C2—C3—H3A	109.5	C26—C25—H25	119.9
N2—C3—H3B	109.5	C21—C26—C25	120.21 (14)
C2—C3—H3B	109.5	C21—C26—H26	119.9
H3A—C3—H3B	108.1	C25—C26—H26	119.9
C4—N2—C3	113.46 (11)	C22—C27—C17	110.76 (11)
C4—N2—H2C	108.3 (12)	C22—C27—H27A	109.5
C3—N2—H2C	110.3 (11)	C17—C27—H27A	109.5
C4—N2—H2D	107.9 (11)	C22—C27—H27B	109.5
C3—N2—H2D	109.0 (11)	C17—C27—H27B	109.5
H2C—N2—H2D	107.8 (16)	H27A—C27—H27B	108.1
N2—C4—H4A	109.5	O33—N31—O32	121.83 (15)
N2—C4—H4B	109.5	O33—N31—C32	118.42 (14)
H4A—C4—H4B	109.5	O32—N31—C32	119.62 (14)
N2—C4—H4C	109.5	O35—N32—O34	122.98 (14)
H4A—C4—H4C	109.5	O35—N32—C34	118.08 (15)
H4B—C4—H4C	109.5	O34—N32—C34	118.94 (15)
C16—C11—C12	118.47 (12)	O36—N33—O37	122.47 (14)
C16—C11—N1	119.19 (12)	O36—N33—C36	118.27 (13)
C12—C11—N1	122.30 (12)	O37—N33—C36	119.21 (13)
C13—C12—C11	118.08 (12)	O31—C31—C32	124.70 (13)
C13—C12—C17	114.98 (12)	O31—C31—C36	123.38 (13)
C11—C12—C17	126.91 (12)	C32—C31—C36	111.91 (12)
C14—C13—C12	122.93 (14)	C33—C32—C31	124.14 (13)
C14—C13—H13	118.5	C33—C32—N31	115.80 (13)
C12—C13—H13	118.5	C31—C32—N31	120.04 (12)
C15—C14—C13	118.78 (14)	C32—C33—C34	119.20 (14)
C15—C14—H14	120.6	C32—C33—H33	120.4
C13—C14—H14	120.6	C34—C33—H33	120.4
C14—C15—C16	120.06 (14)	C33—C34—C35	121.66 (13)
C14—C15—H15	120.0	C33—C34—N32	118.82 (14)
C16—C15—H15	120.0	C35—C34—N32	119.48 (14)
C15—C16—C11	121.67 (14)	C36—C35—C34	118.49 (14)
C15—C16—H16	119.2	C36—C35—H35	120.8
C11—C16—H16	119.2	C34—C35—H35	120.8
C12—C17—C27	117.19 (11)	C35—C36—C31	124.50 (13)
C12—C17—H17A	108.0	C35—C36—N33	116.07 (13)
C27—C17—H17A	108.0	C31—C36—N33	119.41 (12)

C11—N1—C1—C2	157.46 (12)	C22—C21—C26—C25	1.2 (2)
C21—N1—C1—C2	−53.05 (15)	N1—C21—C26—C25	177.85 (12)
N1—C1—C2—C3	−59.70 (15)	C24—C25—C26—C21	−0.8 (2)
C1—C2—C3—N2	−178.70 (11)	C23—C22—C27—C17	−108.52 (14)
C2—C3—N2—C4	−174.77 (11)	C21—C22—C27—C17	68.09 (15)
C21—N1—C11—C16	−132.52 (13)	C12—C17—C27—C22	−65.78 (16)
C1—N1—C11—C16	16.31 (17)	O31—C31—C32—C33	−175.47 (14)
C21—N1—C11—C12	49.96 (17)	C36—C31—C32—C33	3.4 (2)
C1—N1—C11—C12	−161.21 (12)	O31—C31—C32—N31	2.6 (2)
C16—C11—C12—C13	0.94 (19)	C36—C31—C32—N31	−178.59 (13)
N1—C11—C12—C13	178.48 (12)	O33—N31—C32—C33	18.8 (2)
C16—C11—C12—C17	−176.99 (13)	O32—N31—C32—C33	−156.98 (16)
N1—C11—C12—C17	0.6 (2)	O33—N31—C32—C31	−159.42 (18)
C11—C12—C13—C14	−1.4 (2)	O32—N31—C32—C31	24.8 (2)
C17—C12—C13—C14	176.81 (14)	C31—C32—C33—C34	−3.1 (2)
C12—C13—C14—C15	0.5 (3)	N31—C32—C33—C34	178.74 (14)
C13—C14—C15—C16	0.7 (3)	C32—C33—C34—C35	0.5 (2)
C14—C15—C16—C11	−1.1 (2)	C32—C33—C34—N32	178.38 (14)
C12—C11—C16—C15	0.3 (2)	O35—N32—C34—C33	−172.16 (15)
N1—C11—C16—C15	−177.35 (13)	O34—N32—C34—C33	6.9 (2)
C13—C12—C17—C27	−166.15 (13)	O35—N32—C34—C35	5.8 (2)
C11—C12—C17—C27	11.8 (2)	O34—N32—C34—C35	−175.10 (16)
C11—N1—C21—C26	111.04 (14)	C33—C34—C35—C36	1.5 (2)
C1—N1—C21—C26	−38.11 (17)	N32—C34—C35—C36	−176.34 (14)
C11—N1—C21—C22	−72.31 (15)	C34—C35—C36—C31	−1.1 (2)
C1—N1—C21—C22	138.55 (12)	C34—C35—C36—N33	177.23 (14)
C26—C21—C22—C23	−0.66 (19)	O31—C31—C36—C35	177.65 (14)
N1—C21—C22—C23	−177.37 (11)	C32—C31—C36—C35	−1.2 (2)
C26—C21—C22—C27	−177.38 (12)	O31—C31—C36—N33	−0.6 (2)
N1—C21—C22—C27	5.91 (17)	C32—C31—C36—N33	−179.48 (13)
C21—C22—C23—C24	−0.3 (2)	O36—N33—C36—C35	25.7 (2)
C27—C22—C23—C24	176.28 (13)	O37—N33—C36—C35	−151.61 (16)
C22—C23—C24—C25	0.8 (2)	O36—N33—C36—C31	−155.92 (16)
C23—C24—C25—C26	−0.2 (2)	O37—N33—C36—C31	26.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O31	0.90 (2)	1.89 (2)	2.7662 (16)	164 (2)
N2—H2C···O32	0.90 (2)	2.34 (2)	2.8580 (18)	117 (1)
N2—H2D···O31ⁱ	0.92 (2)	2.06 (2)	2.8202 (15)	139 (2)
N2—H2D···O37ⁱ	0.92 (2)	2.38 (2)	3.1873 (18)	148 (2)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃N₂⁺·C₆H₂N₃O₇⁻
M_r	495.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	31.3356 (17), 6.7952 (3), 24.3100 (13)
β (°)	113.542 (4)
V (Å³)	4745.5 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.38 × 0.27 × 0.01

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20306, 5107, 4268
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.636

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.04
No. of reflections	5107
No. of parameters	334
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.40

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O31	0.90 (2)	1.89 (2)	2.7662 (16)	164 (2)
N2—H2C···O32	0.90 (2)	2.34 (2)	2.8580 (18)	117 (1)
N2—H2D···O31ⁱ	0.92 (2)	2.06 (2)	2.8202 (15)	139 (2)
N2—H2D···O37ⁱ	0.92 (2)	2.38 (2)	3.1873 (18)	148 (2)

Symmetry code: (i) −x, y, −z+1/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page