β-Alanine β-alaninium picrate

In the title compound, C₃H₇NO₂·C₃H₈NO₂⁺·C₆H₂N₃O₇⁻, each β-alanine residue forms an asymmetric O—H...O hydrogen bond with its inversion-related partner [O...O = 2.477 (4) and 2.472 (4) Å], involving disorder of carboxylic acid and carboxylate groups. The crystal structure is further stabilized by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.193
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N3
PLAT420_ALERT_2_C D-H Without Acceptor       N21    -   H21C   ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21C   ..  O1      ..       2.63 Ang.

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

   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

hydrogen picrate bis(β-alanine)

Crystal data

H^+·C6H2N3O7^−·2C3H7NO2	Z = 2
Mr = 407.31	F(000) = 424
Triclinic, P1	Dx = 1.615 Mg m^−3 Dm = 1.611 Mg m^−3 Dm measured by flotation in a mixture of carbon tetrachloride and xylene
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9515 (4) Å	Cell parameters from 25 reflections
b = 11.725 (2) Å	θ = 9.9–14.1°
c = 14.931 (2) Å	µ = 0.14 mm^−1
α = 78.00 (1)°	T = 293 K
β = 83.75 (1)°	Needle, yellow
γ = 82.45 (1)°	0.4 × 0.2 × 0.15 mm
V = 837.5 (2) Å^3

Data collection

Nonius MACH3 sealed-tube diffractometer	2537 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.0°, θmin = 2.0°
ω–2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −1→14
Tmin = 0.966, Tmax = 0.979	l = −18→19
4194 measured reflections	3 standard reflections every 60 min
3646 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.193	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1203P)^2 + 0.2829P] where P = (Fo^2 + 2Fc^2)/3
3646 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	1.2193 (5)	0.4188 (2)	0.63130 (15)	0.0449 (5)
N2	1.2124 (6)	0.2545 (2)	0.36075 (16)	0.0541 (7)
N3	0.6314 (5)	0.10285 (19)	0.63024 (16)	0.0455 (5)
O1	0.8754 (4)	0.24869 (17)	0.72821 (12)	0.0462 (5)
O2	1.0835 (6)	0.4583 (3)	0.69170 (19)	0.0814 (9)
O3	1.4521 (5)	0.4442 (3)	0.60584 (18)	0.0748 (7)
O4	1.4187 (6)	0.3007 (3)	0.32960 (15)	0.0779 (8)
O5	1.0867 (6)	0.2053 (3)	0.31615 (15)	0.0738 (7)
O6	0.4913 (5)	0.1186 (2)	0.69968 (15)	0.0594 (6)
O7	0.6051 (7)	0.0224 (2)	0.5923 (2)	0.0881 (9)
C1	1.1157 (5)	0.3335 (2)	0.58907 (16)	0.0374 (5)
C2	1.2117 (5)	0.3318 (2)	0.49988 (17)	0.0404 (6)
H2	1.3413	0.3806	0.4700	0.049*
C3	1.1116 (6)	0.2559 (2)	0.45495 (17)	0.0432 (6)
C4	0.9213 (6)	0.1827 (2)	0.49851 (17)	0.0422 (6)
H4	0.8530	0.1337	0.4669	0.051*
C5	0.8329 (5)	0.1826 (2)	0.58902 (17)	0.0382 (6)
C6	0.9298 (5)	0.2552 (2)	0.64415 (16)	0.0358 (5)
O1A	1.0966 (4)	0.14079 (17)	0.01236 (13)	0.0472 (5)
O1B	1.3585 (4)	−0.01841 (17)	0.07414 (14)	0.0510 (5)
H1B	1.4210	−0.0162	0.0207	0.076*	0.50
C11	1.1512 (5)	0.0602 (2)	0.07667 (17)	0.0344 (5)
C12	0.9827 (6)	0.0482 (2)	0.16680 (19)	0.0432 (6)
H12A	1.0956	0.0567	0.2136	0.052*
H12B	0.9266	−0.0302	0.1830	0.052*
C13	0.7304 (5)	0.1364 (2)	0.1676 (2)	0.0454 (6)
H13A	0.6167	0.1284	0.1208	0.054*
H13B	0.6260	0.1194	0.2267	0.054*
N11	0.7987 (4)	0.25867 (18)	0.15046 (15)	0.0392 (5)
H11A	0.6454	0.3076	0.1514	0.059*
H11B	0.8917	0.2751	0.0958	0.059*
H11C	0.9002	0.2669	0.1939	0.059*
O2A	0.6994 (4)	0.61013 (16)	0.88632 (14)	0.0466 (5)
O2B	0.8837 (5)	0.43951 (17)	0.96091 (17)	0.0566 (6)
H2B	0.9703	0.4823	0.9810	0.085*	0.50
C21	0.7212 (5)	0.5029 (2)	0.90291 (17)	0.0356 (5)
C22	0.5643 (5)	0.4370 (2)	0.85284 (17)	0.0384 (6)
H22A	0.3867	0.4808	0.8420	0.046*
H22B	0.6616	0.4321	0.7935	0.046*
C23	0.5246 (6)	0.3152 (2)	0.90484 (16)	0.0396 (6)
H23A	0.7004	0.2730	0.9206	0.048*
H23B	0.4111	0.3197	0.9615	0.048*
N21	0.3918 (5)	0.25010 (19)	0.84817 (15)	0.0444 (5)
H21A	0.3701	0.1783	0.8799	0.067*
H21B	0.4971	0.2452	0.7966	0.067*
H21C	0.2294	0.2883	0.8345	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0513 (13)	0.0479 (13)	0.0356 (11)	−0.0106 (10)	−0.0002 (10)	−0.0071 (10)
N2	0.0681 (17)	0.0623 (16)	0.0298 (11)	−0.0001 (13)	0.0020 (11)	−0.0116 (11)
N3	0.0501 (13)	0.0376 (12)	0.0468 (12)	−0.0042 (10)	−0.0019 (10)	−0.0055 (10)
O1	0.0570 (12)	0.0500 (11)	0.0301 (9)	−0.0068 (9)	0.0073 (8)	−0.0094 (8)
O2	0.0804 (17)	0.097 (2)	0.0836 (18)	−0.0341 (15)	0.0270 (14)	−0.0594 (16)
O3	0.0676 (16)	0.0905 (19)	0.0737 (16)	−0.0352 (14)	0.0123 (12)	−0.0258 (14)
O4	0.0881 (19)	0.103 (2)	0.0432 (12)	−0.0280 (16)	0.0260 (12)	−0.0210 (13)
O5	0.0954 (19)	0.0946 (19)	0.0384 (11)	−0.0145 (15)	−0.0074 (11)	−0.0259 (12)
O6	0.0629 (13)	0.0625 (13)	0.0530 (12)	−0.0222 (11)	0.0160 (10)	−0.0130 (10)
O7	0.120 (2)	0.0714 (17)	0.0859 (18)	−0.0471 (17)	0.0248 (16)	−0.0389 (15)
C1	0.0393 (13)	0.0406 (13)	0.0315 (12)	−0.0013 (10)	−0.0013 (10)	−0.0079 (10)
C2	0.0412 (13)	0.0463 (14)	0.0304 (12)	−0.0029 (11)	0.0019 (10)	−0.0036 (10)
C3	0.0486 (15)	0.0509 (15)	0.0278 (12)	0.0022 (12)	0.0015 (10)	−0.0094 (11)
C4	0.0470 (14)	0.0436 (14)	0.0367 (13)	0.0017 (11)	−0.0044 (11)	−0.0127 (11)
C5	0.0393 (13)	0.0367 (13)	0.0359 (12)	0.0000 (10)	0.0002 (10)	−0.0057 (10)
C6	0.0390 (12)	0.0351 (12)	0.0301 (11)	0.0012 (10)	0.0022 (9)	−0.0052 (9)
O1A	0.0448 (10)	0.0437 (10)	0.0449 (10)	0.0041 (8)	0.0042 (8)	0.0003 (8)
O1B	0.0547 (12)	0.0426 (11)	0.0525 (11)	0.0136 (9)	−0.0032 (9)	−0.0147 (9)
C11	0.0356 (12)	0.0281 (11)	0.0422 (13)	−0.0060 (9)	−0.0051 (10)	−0.0108 (10)
C12	0.0483 (15)	0.0296 (12)	0.0475 (14)	−0.0049 (11)	0.0080 (11)	−0.0037 (10)
C13	0.0366 (13)	0.0382 (14)	0.0609 (17)	−0.0107 (11)	0.0092 (12)	−0.0119 (12)
N11	0.0375 (11)	0.0330 (11)	0.0464 (12)	−0.0012 (8)	−0.0041 (9)	−0.0074 (9)
O2A	0.0496 (11)	0.0342 (10)	0.0569 (12)	0.0012 (8)	−0.0132 (9)	−0.0103 (8)
O2B	0.0585 (13)	0.0347 (10)	0.0796 (15)	−0.0077 (9)	−0.0322 (11)	−0.0027 (10)
C21	0.0287 (11)	0.0383 (13)	0.0405 (13)	−0.0048 (9)	0.0037 (9)	−0.0119 (10)
C22	0.0428 (13)	0.0352 (13)	0.0373 (12)	−0.0044 (10)	−0.0013 (10)	−0.0080 (10)
C23	0.0472 (14)	0.0399 (13)	0.0318 (12)	−0.0064 (11)	0.0020 (10)	−0.0090 (10)
N21	0.0583 (14)	0.0379 (11)	0.0377 (11)	−0.0158 (10)	−0.0013 (10)	−0.0042 (9)

Geometric parameters (Å, º)

N1—O2	1.200 (3)	C12—C13	1.514 (4)
N1—O3	1.229 (3)	C12—H12A	0.97
N1—C1	1.459 (3)	C12—H12B	0.97
N2—O4	1.221 (4)	C13—N11	1.480 (3)
N2—O5	1.228 (3)	C13—H13A	0.97
N2—C3	1.443 (3)	C13—H13B	0.97
N3—O6	1.216 (3)	N11—H11A	0.89
N3—O7	1.224 (3)	N11—H11B	0.89
N3—C5	1.456 (3)	N11—H11C	0.89
O1—C6	1.243 (3)	O2A—C21	1.222 (3)
C1—C2	1.367 (3)	O2B—C21	1.295 (3)
C1—C6	1.452 (4)	O2B—H2B	0.82
C2—C3	1.388 (4)	C21—C22	1.511 (3)
C2—H2	0.93	C22—C23	1.504 (4)
C3—C4	1.376 (4)	C22—H22A	0.97
C4—C5	1.374 (3)	C22—H22B	0.97
C4—H4	0.93	C23—N21	1.501 (3)
C5—C6	1.456 (4)	C23—H23A	0.97
O1A—C11	1.225 (3)	C23—H23B	0.97
O1B—C11	1.289 (3)	N21—H21A	0.89
O1B—H1B	0.82	N21—H21B	0.89
C11—C12	1.495 (4)	N21—H21C	0.89
O2—N1—O3	121.8 (3)	H12A—C12—H12B	107.6
O2—N1—C1	120.3 (2)	N11—C13—C12	112.3 (2)
O3—N1—C1	117.9 (2)	N11—C13—H13A	109.1
O4—N2—O5	123.2 (3)	C12—C13—H13A	109.1
O4—N2—C3	118.8 (3)	N11—C13—H13B	109.1
O5—N2—C3	117.9 (3)	C12—C13—H13B	109.1
O6—N3—O7	121.8 (3)	H13A—C13—H13B	107.9
O6—N3—C5	119.9 (2)	C13—N11—H11A	109.5
O7—N3—C5	118.3 (2)	C13—N11—H11B	109.5
C2—C1—C6	125.2 (2)	H11A—N11—H11B	109.5
C2—C1—N1	116.0 (2)	C13—N11—H11C	109.5
C6—C1—N1	118.8 (2)	H11A—N11—H11C	109.5
C1—C2—C3	118.5 (2)	H11B—N11—H11C	109.5
C1—C2—H2	120.7	C21—O2B—H2B	109.5
C3—C2—H2	120.7	O2A—C21—O2B	122.9 (2)
C4—C3—C2	121.4 (2)	O2A—C21—C22	120.8 (2)
C4—C3—N2	120.1 (2)	O2B—C21—C22	116.3 (2)
C2—C3—N2	118.5 (2)	C23—C22—C21	113.0 (2)
C5—C4—C3	119.5 (2)	C23—C22—H22A	109.0
C5—C4—H4	120.2	C21—C22—H22A	109.0
C3—C4—H4	120.2	C23—C22—H22B	109.0
C4—C5—N3	116.3 (2)	C21—C22—H22B	109.0
C4—C5—C6	124.1 (2)	H22A—C22—H22B	107.8
N3—C5—C6	119.6 (2)	N21—C23—C22	110.7 (2)
O1—C6—C1	123.2 (2)	N21—C23—H23A	109.5
O1—C6—C5	125.6 (2)	C22—C23—H23A	109.5
C1—C6—C5	111.0 (2)	N21—C23—H23B	109.5
C11—O1B—H1B	109.5	C22—C23—H23B	109.5
O1A—C11—O1B	123.9 (2)	H23A—C23—H23B	108.1
O1A—C11—C12	121.6 (2)	C23—N21—H21A	109.5
O1B—C11—C12	114.5 (2)	C23—N21—H21B	109.5
C11—C12—C13	114.2 (2)	H21A—N21—H21B	109.5
C11—C12—H12A	108.7	C23—N21—H21C	109.5
C13—C12—H12A	108.7	H21A—N21—H21C	109.5
C11—C12—H12B	108.7	H21B—N21—H21C	109.5
C13—C12—H12B	108.7
O2—N1—C1—C2	151.9 (3)	O7—N3—C5—C4	18.1 (4)
O3—N1—C1—C2	−31.2 (4)	O6—N3—C5—C6	20.0 (4)
O2—N1—C1—C6	−30.2 (4)	O7—N3—C5—C6	−161.3 (3)
O3—N1—C1—C6	146.7 (3)	C2—C1—C6—O1	170.1 (3)
C6—C1—C2—C3	4.9 (4)	N1—C1—C6—O1	−7.6 (4)
N1—C1—C2—C3	−177.3 (2)	C2—C1—C6—C5	−6.5 (4)
C1—C2—C3—C4	−0.5 (4)	N1—C1—C6—C5	175.8 (2)
C1—C2—C3—N2	179.8 (2)	C4—C5—C6—O1	−172.3 (2)
O4—N2—C3—C4	−164.9 (3)	N3—C5—C6—O1	7.2 (4)
O5—N2—C3—C4	14.3 (4)	C4—C5—C6—C1	4.2 (3)
O4—N2—C3—C2	14.9 (4)	N3—C5—C6—C1	−176.4 (2)
O5—N2—C3—C2	−166.0 (3)	O1A—C11—C12—C13	5.3 (4)
C2—C3—C4—C5	−1.6 (4)	O1B—C11—C12—C13	−176.6 (2)
N2—C3—C4—C5	178.2 (2)	C11—C12—C13—N11	−62.8 (3)
C3—C4—C5—N3	180.0 (2)	O2A—C21—C22—C23	−157.1 (2)
C3—C4—C5—C6	−0.6 (4)	O2B—C21—C22—C23	25.2 (3)
O6—N3—C5—C4	−160.6 (3)	C21—C22—C23—N21	−174.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O1B^i	0.82	1.70	2.477 (4)	157
N11—H11A···O2A^ii	0.89	1.93	2.775 (3)	159
N11—H11B···O1A	0.89	2.28	2.885 (3)	126
N11—H11B···O2B^iii	0.89	2.48	3.188 (3)	137
N11—H11C···O5	0.89	2.09	2.904 (3)	153
O2B—H2B···O2B^iv	0.82	1.66	2.472 (4)	170
N21—H21A···O1B^v	0.89	2.19	2.894 (3)	136
N21—H21A···O1A^vi	0.89	2.27	2.862 (3)	124
N21—H21B···O1	0.89	2.03	2.830 (3)	148
N21—H21B···O6	0.89	2.28	2.919 (3)	128
N21—H21C···O1^vii	0.89	2.63	3.281 (3)	131

Symmetry codes: (i) −x+3, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+2, −y+1, −z+2; (v) −x+2, −y, −z+1; (vi) x−1, y, z+1; (vii) x−1, y, z.