(R)-Histidinium (2R,3R)-tartrate

The crystal structure of (R)-histidinium (2R,3R)-tartrate, C₆H₁₀N₃O₂⁺·C₄H₅O₆^-, has been determined as part of an ongoing study into the fundamental effects of chirality on salt formation and hydration. Repeating layers of (R)-histidinium and (2R,3R)-tartrate interlink to form a three-dimensional network through simple translational symmetry of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.076
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.802     0.990
            Tmin' and Tmax expected:      0.931     0.986
            RR' =      0.858
            Please check that your absorption correction is appropriate.
STRVA01_ALERT_2_C           Chirality of atom sites is inverted?
           From the CIF: _refine_ls_abs_structure_Flack    1.100
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High ....       1.00
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       1.10
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.25
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5     ..  C3      ..       2.92 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           28.35
           From the CIF: _reflns_number_total               1407
           Count of symmetry unique reflns         1592
           Completeness (_total/calc)             88.38%
           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
   9 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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^−	Z = 1
Mr = 305.25	F(000) = 160
Triclinic, P1	Dx = 1.602 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3712 (18) Å	Cell parameters from 1902 reflections
b = 7.637 (3) Å	θ = 2.6–28.1°
c = 8.460 (3) Å	µ = 0.14 mm^−1
α = 72.025 (5)°	T = 291 K
β = 73.872 (5)°	Tabular, colourless
γ = 81.144 (5)°	0.5 × 0.3 × 0.1 mm
V = 316.2 (2) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	1407 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Thin–slice ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −6→7
Tmin = 0.802, Tmax = 0.990	k = −10→10
2658 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 0.0492P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
1407 reflections	Δρmax = 0.20 e Å^−3
194 parameters	Δρmin = −0.23 e Å^−3
3 restraints	Absolute structure: Flack (1983), 999 friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.1 (10)

Special details

Experimental. The data was collected at room temperature using a Bruker SMART– APEX CCD area-detector (Mo Kα radiation). Intensities were intergrated 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 sphere. The SAINT software containing SADABS was used to intergrate 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.

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

	x	y	z	Uiso*/Ueq
C1	0.3586 (4)	0.6068 (3)	0.9726 (3)	0.0266 (4)
C2	0.1309 (4)	0.5446 (3)	1.0807 (3)	0.0304 (4)
H2	0.0894	0.4222	1.1247	0.037*
C3	0.0985 (5)	0.8457 (3)	1.0290 (3)	0.0345 (5)
H3	0.0345	0.9657	1.0301	0.041*
C4	0.6071 (4)	0.5113 (3)	0.8966 (3)	0.0281 (4)
H4A	0.6592	0.4110	0.9869	0.034*
H4B	0.7413	0.5980	0.8512	0.034*
C5	0.5907 (4)	0.4331 (3)	0.7526 (3)	0.0231 (4)
H5	0.4902	0.5219	0.6783	0.028*
C6	0.4623 (4)	0.2491 (3)	0.8279 (2)	0.0250 (4)
C10	0.3127 (4)	−0.2293 (3)	0.3859 (3)	0.0251 (4)
C9	0.3823 (4)	−0.0281 (3)	0.3345 (3)	0.0242 (4)
H9	0.2383	0.0549	0.2972	0.029*
C8	0.4234 (4)	0.0087 (3)	0.4940 (2)	0.0234 (4)
H8	0.2544	0.0091	0.5766	0.028*
C7	0.5222 (4)	0.2003 (3)	0.4405 (2)	0.0242 (4)
N1	−0.0266 (4)	0.6956 (3)	1.1129 (2)	0.0315 (4)
H1	−0.1819	0.6928	1.1774	0.038*
N2	0.3316 (4)	0.7957 (3)	0.9426 (2)	0.0312 (4)
H2A	0.4480	0.8700	0.8779	0.037*
N3	0.8606 (3)	0.4022 (2)	0.6513 (2)	0.0266 (4)
H3A	0.9285	0.5104	0.5969	0.040*
H3B	0.8575	0.3448	0.5750	0.040*
H3C	0.9570	0.3331	0.7214	0.040*
O1	0.6104 (3)	0.1067 (2)	0.8647 (2)	0.0357 (4)
O2	0.2227 (3)	0.2554 (3)	0.8537 (3)	0.0435 (4)
O7	0.0984 (3)	−0.2658 (2)	0.4859 (2)	0.0378 (4)
O8	0.4788 (3)	−0.3434 (2)	0.3240 (2)	0.0334 (3)
O5	0.6135 (3)	0.0092 (2)	0.20434 (19)	0.0325 (4)
H500	0.5824	0.0285	0.1106	0.049*
O6	0.5920 (3)	−0.1283 (2)	0.57310 (19)	0.0312 (3)
H600	0.7422	−0.1128	0.5170	0.047*
O3	0.3409 (3)	0.3313 (2)	0.4069 (2)	0.0346 (4)
H300	0.3991	0.4321	0.3822	0.052*
O4	0.7451 (3)	0.2238 (2)	0.4303 (2)	0.0368 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0303 (10)	0.0253 (9)	0.0254 (9)	−0.0044 (8)	−0.0058 (8)	−0.0086 (7)
C2	0.0305 (11)	0.0274 (11)	0.0330 (10)	−0.0071 (8)	−0.0041 (9)	−0.0088 (8)
C3	0.0353 (11)	0.0256 (10)	0.0388 (11)	−0.0048 (9)	−0.0002 (9)	−0.0101 (9)
C4	0.0256 (9)	0.0298 (10)	0.0319 (10)	−0.0049 (8)	−0.0057 (8)	−0.0128 (8)
C5	0.0215 (9)	0.0208 (9)	0.0257 (9)	−0.0019 (7)	−0.0047 (7)	−0.0055 (7)
C6	0.0264 (10)	0.0258 (10)	0.0230 (8)	−0.0095 (7)	−0.0046 (7)	−0.0046 (7)
C10	0.0286 (10)	0.0177 (9)	0.0300 (10)	−0.0047 (7)	−0.0064 (8)	−0.0071 (7)
C9	0.0275 (9)	0.0159 (8)	0.0280 (9)	−0.0043 (7)	−0.0036 (8)	−0.0058 (7)
C8	0.0220 (9)	0.0194 (9)	0.0261 (9)	−0.0037 (7)	0.0005 (7)	−0.0070 (7)
C7	0.0283 (9)	0.0213 (9)	0.0234 (9)	−0.0051 (7)	−0.0011 (7)	−0.0098 (7)
N1	0.0284 (9)	0.0318 (9)	0.0311 (9)	−0.0069 (7)	0.0020 (7)	−0.0102 (7)
N2	0.0315 (9)	0.0265 (9)	0.0307 (8)	−0.0084 (7)	0.0018 (7)	−0.0068 (7)
N3	0.0248 (8)	0.0240 (8)	0.0291 (9)	−0.0078 (6)	−0.0001 (7)	−0.0078 (7)
O1	0.0322 (8)	0.0230 (7)	0.0456 (9)	−0.0066 (6)	−0.0066 (7)	−0.0012 (6)
O2	0.0268 (9)	0.0372 (9)	0.0622 (12)	−0.0109 (7)	−0.0113 (8)	−0.0035 (8)
O7	0.0277 (8)	0.0237 (8)	0.0544 (10)	−0.0079 (6)	0.0058 (7)	−0.0114 (7)
O8	0.0335 (8)	0.0197 (7)	0.0435 (9)	−0.0076 (6)	0.0041 (7)	−0.0133 (6)
O5	0.0410 (9)	0.0289 (8)	0.0242 (7)	−0.0127 (7)	0.0021 (6)	−0.0068 (6)
O6	0.0315 (8)	0.0260 (7)	0.0302 (7)	−0.0017 (6)	−0.0049 (6)	−0.0018 (6)
O3	0.0304 (8)	0.0177 (7)	0.0535 (10)	−0.0056 (5)	−0.0057 (7)	−0.0091 (6)
O4	0.0297 (8)	0.0351 (8)	0.0491 (9)	−0.0086 (6)	−0.0085 (7)	−0.0150 (7)

Geometric parameters (Å, º)

C1—C2	1.359 (3)	C10—C9	1.538 (3)
C1—N2	1.377 (3)	C9—O5	1.411 (3)
C1—C4	1.497 (3)	C9—C8	1.539 (3)
C2—N1	1.373 (3)	C9—H9	0.9800
C2—H2	0.9300	C8—O6	1.406 (2)
C3—N1	1.319 (3)	C8—C7	1.525 (3)
C3—N2	1.328 (3)	C8—H8	0.9800
C3—H3	0.9300	C7—O4	1.213 (3)
C4—C5	1.540 (3)	C7—O3	1.307 (3)
C4—H4A	0.9700	N1—H1	0.8600
C4—H4B	0.9700	N2—H2A	0.8600
C5—N3	1.490 (3)	N3—H3A	0.8900
C5—C6	1.536 (3)	N3—H3B	0.8900
C5—H5	0.9800	N3—H3C	0.8900
C6—O2	1.240 (3)	O5—H500	0.8200
C6—O1	1.255 (3)	O6—H600	0.8200
C10—O7	1.237 (3)	O3—H300	0.8200
C10—O8	1.269 (3)
C2—C1—N2	105.75 (18)	C10—C9—C8	107.52 (16)
C2—C1—C4	133.0 (2)	O5—C9—H9	109.5
N2—C1—C4	121.18 (19)	C10—C9—H9	109.5
C1—C2—N1	107.40 (19)	C8—C9—H9	109.5
C1—C2—H2	126.3	O6—C8—C7	111.96 (16)
N1—C2—H2	126.3	O6—C8—C9	112.15 (15)
N1—C3—N2	108.2 (2)	C7—C8—C9	108.21 (15)
N1—C3—H3	125.9	O6—C8—H8	108.1
N2—C3—H3	125.9	C7—C8—H8	108.1
C1—C4—C5	114.23 (17)	C9—C8—H8	108.1
C1—C4—H4A	108.7	O4—C7—O3	125.39 (19)
C5—C4—H4A	108.7	O4—C7—C8	122.49 (19)
C1—C4—H4B	108.7	O3—C7—C8	112.12 (17)
C5—C4—H4B	108.7	C3—N1—C2	109.1 (2)
H4A—C4—H4B	107.6	C3—N1—H1	125.5
N3—C5—C6	109.32 (16)	C2—N1—H1	125.5
N3—C5—C4	107.87 (16)	C3—N2—C1	109.61 (18)
C6—C5—C4	110.70 (17)	C3—N2—H2A	125.2
N3—C5—H5	109.6	C1—N2—H2A	125.2
C6—C5—H5	109.6	C5—N3—H3A	109.5
C4—C5—H5	109.6	C5—N3—H3B	109.5
O2—C6—O1	126.2 (2)	H3A—N3—H3B	109.5
O2—C6—C5	117.46 (19)	C5—N3—H3C	109.5
O1—C6—C5	116.27 (17)	H3A—N3—H3C	109.5
O7—C10—O8	125.67 (19)	H3B—N3—H3C	109.5
O7—C10—C9	116.51 (18)	C9—O5—H500	109.5
O8—C10—C9	117.82 (18)	C8—O6—H600	109.5
O5—C9—C10	113.51 (16)	C7—O3—H300	109.5
O5—C9—C8	107.33 (16)
N2—C1—C2—N1	0.1 (2)	O5—C9—C8—O6	−72.73 (19)
C4—C1—C2—N1	177.5 (2)	C10—C9—C8—O6	49.7 (2)
C2—C1—C4—C5	74.0 (3)	O5—C9—C8—C7	51.25 (19)
N2—C1—C4—C5	−108.9 (2)	C10—C9—C8—C7	173.71 (16)
C1—C4—C5—N3	160.87 (17)	O6—C8—C7—O4	16.5 (3)
C1—C4—C5—C6	−79.6 (2)	C9—C8—C7—O4	−107.6 (2)
N3—C5—C6—O2	−151.42 (19)	O6—C8—C7—O3	−164.12 (16)
C4—C5—C6—O2	89.9 (2)	C9—C8—C7—O3	71.8 (2)
N3—C5—C6—O1	31.7 (2)	N2—C3—N1—C2	0.4 (3)
C4—C5—C6—O1	−87.0 (2)	C1—C2—N1—C3	−0.3 (3)
O7—C10—C9—O5	−172.49 (18)	N1—C3—N2—C1	−0.4 (3)
O8—C10—C9—O5	8.1 (3)	C2—C1—N2—C3	0.2 (2)
O7—C10—C9—C8	69.0 (2)	C4—C1—N2—C3	−177.6 (2)
O8—C10—C9—C8	−110.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O8^i	0.86	1.90	2.760 (2)	173
N1—H1···O5^i	0.86	2.55	2.993 (3)	113
N2—H2A···O1^ii	0.86	2.09	2.810 (3)	142
N2—H2A···O6^ii	0.86	2.47	2.961 (3)	117
N3—H3A···O7^iii	0.89	1.91	2.799 (2)	176
N3—H3C···O2^iv	0.89	1.96	2.822 (3)	162
O5—H500···O1^v	0.82	1.95	2.741 (3)	163
O6—H600···O7^iv	0.82	2.08	2.744 (2)	138
O3—H300···O8^ii	0.82	1.72	2.533 (2)	172

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