(2S)-2-(3-Benzoyl­thio­ureido)-3-(1H-imidazol-4-yl)­propionic acid

The title compound, (2S)-2-(3-benzoyl­thio­ureido)-3-(1H-imidazolium-4-yl)­propionate, C₁₄H₁₄N₄O₃S, is zwitterionic with protonated positively charged imidazoyl and deproton­ated negatively charged carboxyl­ate groups. The intermolec­ular hydrogen bonds, C—H...O and N—H...O, involve all the O atoms with the H atoms from the amine and imidazoyl­ium, forming a two-dimensional network parallel to the (100) plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.097
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.08
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               1678
           Count of symmetry unique reflns         1689
           Completeness (_total/calc)             99.35%
           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          yes

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

(9S)-2-(3-benzoylthioureido)-3-(1H-imidazolium-4-yl)propionate

Crystal data

C14H14N4O3S	F(000) = 332
Mr = 318.35	Dx = 1.488 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2717 reflections
a = 5.6995 (13) Å	θ = 2.2–27.5°
b = 17.916 (4) Å	µ = 0.25 mm^−1
c = 7.0525 (17) Å	T = 298 K
β = 99.424 (5)°	Block, colourless
V = 710.4 (3) Å^3	0.29 × 0.27 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1678 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→23
Tmin = 0.931, Tmax = 0.952	l = −9→8
4765 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.1656P] where P = (Fo^2 + 2Fc^2)/3
1678 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.32 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.44510 (16)	1.03238 (4)	0.96921 (12)	0.0483 (2)
O1	0.5463 (4)	0.79580 (11)	0.7691 (3)	0.0403 (5)
O2	−0.0259 (5)	0.85282 (13)	0.5253 (4)	0.0583 (7)
O3	−0.1620 (5)	0.94687 (13)	0.3377 (4)	0.0496 (6)
N1	0.6404 (4)	0.89898 (13)	0.9566 (4)	0.0348 (5)
H1A	0.7334	0.9148	1.0570	0.042*
N2	0.3391 (4)	0.92673 (14)	0.7074 (3)	0.0348 (5)
H2A	0.3645	0.8829	0.6652	0.042*
C14	0.1589 (6)	1.17047 (18)	0.4594 (5)	0.0416 (7)
H14A	0.3036	1.1909	0.5159	0.050*
C13	−0.2093 (6)	1.16234 (18)	0.3237 (5)	0.0437 (8)
H13A	−0.3642	1.1748	0.2697	0.052*
C1	0.8711 (6)	0.71091 (18)	1.0250 (5)	0.0369 (6)
H1B	0.7312	0.6864	0.9738	0.044*
C2	1.0637 (6)	0.6703 (2)	1.1133 (5)	0.0467 (8)
H2B	1.0539	0.6186	1.1232	0.056*
C3	1.2701 (6)	0.7070 (2)	1.1867 (5)	0.0504 (9)
H3A	1.4026	0.6796	1.2418	0.061*
C4	1.2837 (6)	0.7829 (2)	1.1797 (5)	0.0496 (9)
H4A	1.4227	0.8070	1.2350	0.060*
C5	1.0912 (5)	0.8245 (2)	1.0904 (5)	0.0405 (7)
H5A	1.1013	0.8762	1.0835	0.049*
C6	0.8841 (5)	0.78795 (17)	1.0119 (4)	0.0329 (6)
C7	0.6754 (5)	0.82725 (16)	0.9002 (4)	0.0311 (6)
C8	0.4711 (5)	0.94858 (16)	0.8687 (4)	0.0315 (6)
C9	0.1532 (5)	0.97163 (15)	0.5955 (4)	0.0315 (6)
H9A	0.0699	0.9987	0.6853	0.038*
C10	−0.0271 (6)	0.91853 (17)	0.4753 (4)	0.0361 (6)
C11	0.2616 (5)	1.0296 (2)	0.4732 (4)	0.0377 (6)
H11A	0.4165	1.0443	0.5413	0.045*
H11B	0.2850	1.0063	0.3535	0.045*
C12	0.1135 (5)	1.09724 (17)	0.4289 (4)	0.0327 (6)
N4	−0.0425 (5)	1.20926 (15)	0.3938 (4)	0.0415 (6)
H4B	−0.0577	1.2570	0.3979	0.050*
N3	−0.1210 (5)	1.09424 (15)	0.3423 (4)	0.0377 (6)
H3C	−0.1981	1.0541	0.3059	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0619 (5)	0.0265 (4)	0.0475 (4)	0.0097 (4)	−0.0175 (3)	−0.0095 (3)
O1	0.0449 (12)	0.0241 (10)	0.0461 (12)	0.0068 (9)	−0.0096 (9)	−0.0050 (9)
O2	0.0723 (17)	0.0250 (12)	0.0663 (16)	−0.0032 (12)	−0.0223 (13)	0.0095 (11)
O3	0.0621 (14)	0.0265 (11)	0.0486 (13)	0.0002 (11)	−0.0256 (11)	−0.0010 (10)
N1	0.0380 (12)	0.0258 (12)	0.0352 (13)	0.0012 (10)	−0.0102 (10)	−0.0017 (10)
N2	0.0450 (13)	0.0229 (12)	0.0314 (12)	0.0056 (10)	−0.0090 (10)	−0.0004 (9)
C14	0.0495 (18)	0.0312 (16)	0.0407 (16)	−0.0061 (14)	−0.0028 (13)	0.0013 (12)
C13	0.0483 (18)	0.0336 (17)	0.0466 (18)	0.0081 (14)	−0.0005 (14)	0.0035 (14)
C1	0.0388 (15)	0.0336 (15)	0.0368 (16)	0.0045 (13)	0.0014 (12)	0.0038 (12)
C2	0.0513 (18)	0.0403 (19)	0.0478 (18)	0.0142 (16)	0.0061 (15)	0.0114 (14)
C3	0.0406 (17)	0.062 (2)	0.0469 (19)	0.0192 (17)	0.0015 (14)	0.0098 (16)
C4	0.0308 (15)	0.069 (3)	0.047 (2)	0.0023 (15)	−0.0003 (14)	0.0021 (17)
C5	0.0350 (15)	0.0400 (17)	0.0451 (17)	0.0007 (13)	0.0022 (13)	0.0001 (14)
C6	0.0321 (14)	0.0359 (15)	0.0296 (15)	0.0057 (12)	0.0018 (11)	0.0023 (11)
C7	0.0329 (13)	0.0269 (13)	0.0311 (13)	0.0023 (11)	−0.0018 (11)	0.0030 (11)
C8	0.0367 (13)	0.0215 (12)	0.0334 (14)	0.0012 (11)	−0.0031 (11)	0.0015 (11)
C9	0.0373 (14)	0.0222 (12)	0.0312 (13)	0.0060 (11)	−0.0057 (11)	0.0000 (10)
C10	0.0457 (16)	0.0238 (13)	0.0354 (15)	0.0012 (12)	−0.0041 (13)	−0.0022 (11)
C11	0.0417 (14)	0.0300 (14)	0.0393 (14)	0.0038 (14)	0.0000 (11)	0.0068 (13)
C12	0.0396 (14)	0.0273 (14)	0.0290 (13)	0.0001 (12)	−0.0010 (10)	0.0052 (11)
N4	0.0646 (17)	0.0197 (11)	0.0380 (14)	0.0020 (12)	0.0013 (12)	−0.0001 (10)
N3	0.0404 (13)	0.0229 (11)	0.0453 (14)	−0.0006 (10)	−0.0061 (11)	−0.0005 (10)

Geometric parameters (Å, º)

S1—C8	1.677 (3)	C2—C3	1.373 (6)
O1—C7	1.221 (4)	C2—H2B	0.9300
O2—C10	1.229 (4)	C3—C4	1.364 (6)
O3—C10	1.244 (4)	C3—H3A	0.9300
N1—C7	1.369 (4)	C4—C5	1.390 (5)
N1—C8	1.382 (4)	C4—H4A	0.9300
N1—H1A	0.8600	C5—C6	1.384 (4)
N2—C8	1.316 (4)	C5—H5A	0.9300
N2—C9	1.456 (3)	C6—C7	1.492 (4)
N2—H2A	0.8600	C9—C11	1.542 (4)
C14—C12	1.348 (4)	C9—C10	1.547 (4)
C14—N4	1.357 (4)	C9—H9A	0.9800
C14—H14A	0.9300	C11—C12	1.481 (4)
C13—N4	1.304 (4)	C11—H11A	0.9700
C13—N3	1.318 (4)	C11—H11B	0.9700
C13—H13A	0.9300	C12—N3	1.377 (4)
C1—C2	1.378 (4)	N4—H4B	0.8600
C1—C6	1.386 (4)	N3—H3C	0.8600
C1—H1B	0.9300
C7—N1—C8	126.7 (2)	O1—C7—N1	123.7 (3)
C7—N1—H1A	116.7	O1—C7—C6	120.8 (3)
C8—N1—H1A	116.7	N1—C7—C6	115.5 (2)
C8—N2—C9	124.5 (2)	N2—C8—N1	117.0 (3)
C8—N2—H2A	117.7	N2—C8—S1	123.6 (2)
C9—N2—H2A	117.7	N1—C8—S1	119.3 (2)
C12—C14—N4	108.3 (3)	N2—C9—C11	110.6 (2)
C12—C14—H14A	125.8	N2—C9—C10	108.4 (2)
N4—C14—H14A	125.8	C11—C9—C10	113.5 (2)
N4—C13—N3	108.4 (3)	N2—C9—H9A	108.0
N4—C13—H13A	125.8	C11—C9—H9A	108.0
N3—C13—H13A	125.8	C10—C9—H9A	108.0
C2—C1—C6	120.6 (3)	O2—C10—O3	126.1 (3)
C2—C1—H1B	119.7	O2—C10—C9	117.4 (3)
C6—C1—H1B	119.7	O3—C10—C9	116.5 (3)
C3—C2—C1	119.2 (3)	C12—C11—C9	113.8 (2)
C3—C2—H2B	120.4	C12—C11—H11A	108.8
C1—C2—H2B	120.4	C9—C11—H11A	108.8
C4—C3—C2	120.9 (3)	C12—C11—H11B	108.8
C4—C3—H3A	119.5	C9—C11—H11B	108.8
C2—C3—H3A	119.5	H11A—C11—H11B	107.7
C3—C4—C5	120.4 (4)	C14—C12—N3	104.8 (3)
C3—C4—H4A	119.8	C14—C12—C11	132.5 (3)
C5—C4—H4A	119.8	N3—C12—C11	122.7 (3)
C6—C5—C4	119.1 (3)	C13—N4—C14	108.8 (3)
C6—C5—H5A	120.5	C13—N4—H4B	125.6
C4—C5—H5A	120.5	C14—N4—H4B	125.6
C5—C6—C1	119.7 (3)	C13—N3—C12	109.6 (3)
C5—C6—C7	122.8 (3)	C13—N3—H3C	125.2
C1—C6—C7	117.3 (3)	C12—N3—H3C	125.2
C6—C1—C2—C3	−0.7 (5)	C8—N2—C9—C11	79.5 (4)
C1—C2—C3—C4	2.5 (6)	C8—N2—C9—C10	−155.5 (3)
C2—C3—C4—C5	−2.8 (6)	N2—C9—C10—O2	18.2 (4)
C3—C4—C5—C6	1.2 (5)	C11—C9—C10—O2	141.6 (3)
C4—C5—C6—C1	0.6 (5)	N2—C9—C10—O3	−162.5 (3)
C4—C5—C6—C7	−175.1 (3)	C11—C9—C10—O3	−39.1 (4)
C2—C1—C6—C5	−0.8 (5)	N2—C9—C11—C12	−153.1 (2)
C2—C1—C6—C7	175.1 (3)	C10—C9—C11—C12	84.7 (3)
C8—N1—C7—O1	−5.5 (5)	N4—C14—C12—N3	0.3 (4)
C8—N1—C7—C6	175.2 (3)	N4—C14—C12—C11	−178.7 (3)
C5—C6—C7—O1	148.1 (3)	C9—C11—C12—C14	124.1 (4)
C1—C6—C7—O1	−27.7 (4)	C9—C11—C12—N3	−54.8 (4)
C5—C6—C7—N1	−32.6 (4)	N3—C13—N4—C14	0.0 (4)
C1—C6—C7—N1	151.6 (3)	C12—C14—N4—C13	−0.2 (4)
C9—N2—C8—N1	−179.8 (3)	N4—C13—N3—C12	0.2 (4)
C9—N2—C8—S1	−0.4 (4)	C14—C12—N3—C13	−0.3 (4)
C7—N1—C8—N2	−4.6 (4)	C11—C12—N3—C13	178.8 (3)
C7—N1—C8—S1	175.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···S1	0.98	2.75	3.076 (3)	100
N2—H2A···O1	0.86	1.95	2.630 (3)	135
N3—H3C···O3	0.86	1.94	2.650 (4)	139
N1—H1A···O3^i	0.86	2.05	2.870 (4)	158
N4—H4B···O2^ii	0.86	1.84	2.650 (4)	156
C13—H13A···O1^ii	0.93	2.40	3.070 (4)	129

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