D-Histidinium (2S,3S)-tartrate

The crystal structure of the title compound, C₆H₁₀N₃O₂⁺·C₄H₅O₆^-, has been determined as part of an ongoing study into the fundamental effects of chirality on salt formation and hydration. This structure has distinct layers of histidine, which are linked by stacks of tartrates, forming a complex three-dimensional hydrogen-bond network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.057
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.88
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C5      ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C3      ..       2.99 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.09
           From the CIF: _reflns_number_total               1334
           Count of symmetry unique reflns         1336
           Completeness (_total/calc)             99.85%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

---

Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1996) and Materials Studio (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C6H10N3O2^+·C4H5O6^−	F(000) = 640
Mr = 305.25	Dx = 1.604 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2110 reflections
a = 5.0207 (9) Å	θ = 2.6–22.4°
b = 12.109 (2) Å	µ = 0.14 mm^−1
c = 20.797 (4) Å	T = 295 K
V = 1264.4 (4) Å^3	Needle, colourless
Z = 4	0.40 × 0.10 × 0.05 mm

Data collection

Siemens SMART APEX CCD diffractometer	1334 independent reflections
Radiation source: fine-focus sealed tube	1117 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 67 pixels mm^-1	θmax = 25.1°, θmin = 2.0°
Thin–slice ω scans	h = −3→5
Absorption correction: multi-scan (Blessing, 1995)	k = −13→14
Tmin = 0.941, Tmax = 0.998	l = −23→24
6322 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.057	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.019P)^2] where P = (Fo^2 + 2Fc^2)/3
1334 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. The data was collected at room temperature using a Bruker AXS SMART– APEX CCD area-detector (Mo Kα radiation). Intensities were integrated from a series of exposures. Each exposure covered 0.3° in ω, with an exposure time of 60 s and the total data set was more than a hemisphere. The SAINT software containing SADABS was used to integrate and correct the data.

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.

MERG 3 inserted in instruction file to merg all friedel pairs prior to least squares refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5828 (5)	0.03063 (19)	0.32085 (11)	0.0274 (6)
C2	0.7235 (5)	−0.0158 (2)	0.27282 (12)	0.0349 (6)
H2	0.7054	−0.0011	0.2291	0.042*
C3	0.8663 (6)	−0.0862 (2)	0.36268 (13)	0.0392 (7)
H3	0.9616	−0.1279	0.3924	0.047*
C4	0.3684 (5)	0.11467 (18)	0.32007 (11)	0.0305 (6)
H4A	0.2245	0.0889	0.3473	0.037*
H4B	0.2993	0.1198	0.2766	0.037*
C5	0.4473 (5)	0.23026 (19)	0.34208 (11)	0.0300 (6)
H5	0.3076	0.2810	0.3276	0.036*
C6	0.7087 (5)	0.27209 (19)	0.31508 (12)	0.0277 (6)
C7	0.5204 (6)	0.19402 (19)	0.11514 (12)	0.0327 (6)
C8	0.3547 (5)	0.14123 (18)	0.06330 (10)	0.0283 (6)
H8	0.1704	0.1670	0.0671	0.034*
C9	0.3612 (5)	0.01531 (19)	0.07077 (10)	0.0291 (6)
H9	0.2422	−0.0032	0.1066	0.035*
C10	0.2460 (5)	−0.0390 (2)	0.01085 (12)	0.0322 (6)
N1	0.8983 (4)	−0.08880 (16)	0.30024 (10)	0.0391 (6)
H1	1.0103	−0.1295	0.2798	0.047*
N2	0.6779 (4)	−0.01512 (16)	0.37654 (9)	0.0340 (5)
H2A	0.6226	0.0003	0.4146	0.041*
N3	0.4589 (5)	0.23784 (18)	0.41277 (10)	0.0473 (6)
H3A	0.6164	0.2136	0.4265	0.071*
H3B	0.3302	0.1966	0.4298	0.071*
H3C	0.4371	0.3078	0.4247	0.071*
O1	0.8800 (4)	0.30273 (15)	0.35291 (8)	0.0439 (5)
O2	0.7275 (4)	0.27511 (14)	0.25462 (8)	0.0434 (5)
O3	0.4282 (4)	0.17651 (15)	0.17279 (8)	0.0435 (5)
H3D	0.5209	0.2092	0.1991	0.065*
O4	0.7156 (4)	0.24775 (16)	0.10423 (8)	0.0536 (6)
O5	0.4566 (4)	0.17257 (15)	0.00294 (8)	0.0384 (5)
H5A	0.3427	0.2071	−0.0169	0.058*
O6	0.6163 (3)	−0.02466 (14)	0.08717 (8)	0.0338 (4)
H6	0.7191	−0.0140	0.0572	0.051*
O7	0.0131 (3)	−0.01179 (16)	−0.00399 (8)	0.0452 (5)
O8	0.3848 (4)	−0.10665 (14)	−0.01880 (8)	0.0423 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0313 (14)	0.0219 (12)	0.0289 (13)	−0.0060 (12)	−0.0007 (12)	0.0008 (11)
C2	0.0423 (16)	0.0323 (14)	0.0300 (14)	−0.0013 (13)	0.0023 (12)	−0.0029 (12)
C3	0.0422 (17)	0.0275 (15)	0.0478 (18)	0.0047 (14)	0.0036 (14)	0.0050 (13)
C4	0.0281 (13)	0.0302 (14)	0.0331 (13)	−0.0056 (12)	0.0033 (12)	0.0029 (11)
C5	0.0260 (14)	0.0236 (13)	0.0406 (15)	0.0016 (11)	0.0052 (11)	0.0024 (11)
C6	0.0256 (14)	0.0219 (13)	0.0356 (15)	0.0028 (11)	0.0028 (12)	−0.0020 (11)
C7	0.0413 (17)	0.0256 (13)	0.0312 (14)	0.0049 (13)	0.0035 (12)	0.0033 (11)
C8	0.0278 (13)	0.0292 (13)	0.0278 (13)	0.0022 (12)	0.0011 (11)	0.0053 (10)
C9	0.0268 (13)	0.0315 (13)	0.0291 (14)	−0.0013 (12)	−0.0039 (11)	0.0084 (11)
C10	0.0322 (15)	0.0343 (15)	0.0302 (14)	−0.0095 (14)	−0.0024 (12)	0.0063 (11)
N1	0.0430 (14)	0.0272 (12)	0.0472 (14)	0.0037 (11)	0.0128 (12)	−0.0085 (10)
N2	0.0404 (13)	0.0296 (12)	0.0320 (12)	0.0031 (11)	0.0068 (10)	0.0014 (10)
N3	0.0606 (16)	0.0350 (12)	0.0464 (13)	−0.0170 (12)	0.0243 (12)	−0.0134 (11)
O1	0.0270 (10)	0.0598 (13)	0.0449 (11)	−0.0062 (10)	0.0019 (9)	−0.0118 (9)
O2	0.0496 (12)	0.0468 (11)	0.0338 (11)	−0.0166 (10)	0.0075 (9)	0.0027 (9)
O3	0.0484 (13)	0.0534 (12)	0.0286 (10)	−0.0140 (10)	0.0017 (9)	−0.0017 (9)
O4	0.0618 (14)	0.0597 (13)	0.0394 (12)	−0.0325 (13)	0.0091 (10)	−0.0031 (9)
O5	0.0476 (12)	0.0371 (11)	0.0306 (10)	0.0039 (9)	0.0015 (8)	0.0111 (8)
O6	0.0314 (10)	0.0316 (9)	0.0384 (10)	0.0020 (9)	−0.0088 (8)	0.0029 (9)
O7	0.0317 (10)	0.0667 (14)	0.0371 (11)	0.0016 (10)	−0.0108 (8)	−0.0007 (9)
O8	0.0436 (11)	0.0371 (10)	0.0460 (11)	0.0021 (10)	−0.0093 (9)	−0.0120 (9)

Geometric parameters (Å, º)

C1—C2	1.347 (3)	C7—O3	1.303 (3)
C1—N2	1.370 (3)	C7—C8	1.504 (3)
C1—C4	1.481 (3)	C8—O5	1.408 (3)
C2—N1	1.370 (3)	C8—C9	1.533 (3)
C2—H2	0.9300	C8—H8	0.9800
C3—N1	1.309 (3)	C9—O6	1.411 (3)
C3—N2	1.311 (3)	C9—C10	1.523 (3)
C3—H3	0.9300	C9—H9	0.9800
C4—C5	1.525 (3)	C10—O8	1.240 (3)
C4—H4A	0.9700	C10—O7	1.253 (3)
C4—H4B	0.9700	N1—H1	0.8600
C5—N3	1.474 (3)	N2—H2A	0.8600
C5—C6	1.515 (3)	N3—H3A	0.8900
C5—H5	0.9800	N3—H3B	0.8900
C6—O1	1.223 (3)	N3—H3C	0.8900
C6—O2	1.261 (3)	O3—H3D	0.8200
C6—O2	1.261 (3)	O5—H5A	0.8200
C7—O4	1.198 (3)	O6—H6	0.8200
C2—C1—N2	106.0 (2)	O5—C8—C9	110.54 (18)
C2—C1—C4	131.3 (2)	C7—C8—C9	109.78 (19)
N2—C1—C4	122.7 (2)	O5—C8—H8	109.2
C1—C2—N1	107.3 (2)	C7—C8—H8	109.2
C1—C2—H2	126.4	C9—C8—H8	109.2
N1—C2—H2	126.4	O6—C9—C10	113.2 (2)
N1—C3—N2	108.8 (2)	O6—C9—C8	112.63 (19)
N1—C3—H3	125.6	C10—C9—C8	109.76 (18)
N2—C3—H3	125.6	O6—C9—H9	106.9
C1—C4—C5	116.0 (2)	C10—C9—H9	106.9
C1—C4—H4A	108.3	C8—C9—H9	106.9
C5—C4—H4A	108.3	O8—C10—O7	125.1 (2)
C1—C4—H4B	108.3	O8—C10—C9	118.6 (2)
C5—C4—H4B	108.3	O7—C10—C9	116.3 (2)
H4A—C4—H4B	107.4	C3—N1—C2	108.6 (2)
N3—C5—C6	108.3 (2)	C3—N1—H1	125.7
N3—C5—C4	111.51 (19)	C2—N1—H1	125.7
C6—C5—C4	114.9 (2)	C3—N2—C1	109.3 (2)
N3—C5—H5	107.2	C3—N2—H2A	125.3
C6—C5—H5	107.2	C1—N2—H2A	125.3
C4—C5—H5	107.2	C5—N3—H3A	109.5
O1—C6—O2	125.4 (2)	C5—N3—H3B	109.5
O1—C6—O2	125.4 (2)	H3A—N3—H3B	109.5
O1—C6—C5	118.2 (2)	C5—N3—H3C	109.5
O2—C6—C5	116.4 (2)	H3A—N3—H3C	109.5
O2—C6—C5	116.4 (2)	H3B—N3—H3C	109.5
O4—C7—O3	123.6 (2)	C7—O3—H3D	109.5
O4—C7—C8	123.2 (2)	C8—O5—H5A	109.5
O3—C7—C8	113.2 (2)	C9—O6—H6	109.5
O5—C8—C7	108.9 (2)
N2—C1—C2—N1	0.4 (3)	O5—C8—C9—O6	79.5 (2)
C4—C1—C2—N1	179.9 (2)	C7—C8—C9—O6	−40.6 (3)
C2—C1—C4—C5	−105.5 (3)	O5—C8—C9—C10	−47.6 (3)
N2—C1—C4—C5	73.9 (3)	C7—C8—C9—C10	−167.7 (2)
C1—C4—C5—N3	−79.1 (3)	O6—C9—C10—O8	−3.2 (3)
C1—C4—C5—C6	44.6 (3)	C8—C9—C10—O8	123.6 (2)
N3—C5—C6—O1	0.7 (3)	O6—C9—C10—O7	175.8 (2)
C4—C5—C6—O1	−124.7 (2)	C8—C9—C10—O7	−57.3 (3)
N3—C5—C6—O2	−177.35 (19)	N2—C3—N1—C2	0.3 (3)
C4—C5—C6—O2	57.2 (3)	C1—C2—N1—C3	−0.4 (3)
N3—C5—C6—O2	−177.35 (19)	N1—C3—N2—C1	0.0 (3)
C4—C5—C6—O2	57.2 (3)	C2—C1—N2—C3	−0.3 (3)
O4—C7—C8—O5	−4.2 (3)	C4—C1—N2—C3	−179.8 (2)
O3—C7—C8—O5	175.00 (19)	O1—C6—O2—O2	0.0 (4)
O4—C7—C8—C9	116.9 (2)	C5—C6—O2—O2	0.0 (3)
O3—C7—C8—C9	−63.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	1.89	2.747 (3)	173
N2—H2A···O7^ii	0.86	1.83	2.683 (3)	171
N3—H3B···O8^ii	0.89	1.87	2.743 (3)	167
N3—H3C···O6^iii	0.89	2.06	2.901 (3)	157
N3—H3C···O8^iii	0.89	2.39	3.004 (3)	127
O5—H5A···O4^iv	0.82	2.00	2.713 (2)	145
O5—H5A···O5^iv	0.82	2.44	3.136 (2)	143
O6—H6···O7^v	0.82	1.95	2.754 (2)	167
O3—H3D···O2	0.82	1.75	2.565 (2)	178

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