3-(1H-1,2,4-Triazol-3-yl­sulfanyl­methyl)­benzoic acid

The title compound, C₁₀H₉N₃O₂S, crystallizes in the ortho­rhombic non-centrosymmetric space group P2₁2₁2₁. The mol­ecules are linked into a three-dimensional network through O—H...N and N—H...O hydrogen bonds and weak S...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.058
• wR factor = 0.133
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.00 Deg.
              N1   -O2   -H2B     4.646   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       6.70 Deg.
              O1   -N2   -H2A     3.456   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.20

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           25.08
           From the CIF: _reflns_number_total               1827
           Count of symmetry unique reflns         1101
           Completeness (_total/calc)            165.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       726
           Fraction of Friedel pairs measured     0.659
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-(1H-1,2,4-Triazole-3-ylsulfanylmethyl)benzoic acid

Crystal data

C10H9N3O2S	Dx = 1.507 Mg m^−3
Mr = 235.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3393 reflections
a = 5.5079 (1) Å	θ = 2.1–25.1°
b = 13.1233 (6) Å	µ = 0.30 mm^−1
c = 14.3414 (7) Å	T = 293 K
V = 1036.62 (7) Å^3	Needle, colorless
Z = 4	0.20 × 0.10 × 0.08 mm
F(000) = 488

Data collection

Bruker SMART CCD diffractometer	1827 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.192 pixels mm^-1	θmax = 25.1°, θmin = 2.1°
ω scans	h = −6→6
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −10→15
Tmin = 0.972, Tmax = 0.978	l = −17→8
3393 measured reflections

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + 1.1042P] where P = (Fo^2 + 2Fc^2)/3
S = 1.26	(Δ/σ)max = 0.001
1827 reflections	Δρmax = 0.22 e Å^−3
145 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (2)

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
S1	0.1935 (2)	0.39942 (10)	0.59974 (8)	0.0450 (4)
O1	0.3858 (7)	0.0518 (3)	0.8240 (2)	0.0494 (10)
O2	0.2440 (6)	0.1033 (3)	0.96117 (19)	0.0487 (10)
H2B	0.3493	0.0623	0.9807	0.073*
N1	0.3821 (9)	0.5052 (3)	0.4555 (3)	0.0472 (12)
N2	0.1353 (9)	0.4655 (3)	0.3428 (2)	0.0444 (12)
H2A	0.0692	0.4645	0.2869	0.053*
N3	0.0489 (8)	0.4124 (3)	0.4183 (3)	0.0438 (11)
C1	0.3300 (12)	0.5180 (4)	0.3651 (3)	0.0484 (14)
H1A	0.4206	0.5592	0.3232	0.058*
C2	0.2044 (10)	0.4408 (4)	0.4831 (3)	0.0365 (12)
C3	−0.0471 (10)	0.3048 (3)	0.5944 (3)	0.0415 (12)
H3A	−0.1990	0.3354	0.5704	0.050*
H3B	−0.0001	0.2475	0.5532	0.050*
C4	−0.0809 (10)	0.2681 (3)	0.6944 (3)	0.0363 (12)
C5	−0.2707 (10)	0.3059 (4)	0.7473 (3)	0.0410 (13)
H5A	−0.3846	0.3514	0.7201	0.049*
C6	−0.2952 (10)	0.2773 (4)	0.8406 (3)	0.0430 (12)
H6A	−0.4271	0.3026	0.8765	0.052*
C7	−0.1279 (9)	0.2124 (4)	0.8807 (3)	0.0388 (12)
H7A	−0.1432	0.1942	0.9446	0.047*
C8	0.0618 (9)	0.1737 (3)	0.8284 (3)	0.0328 (11)
C9	0.0854 (10)	0.2015 (3)	0.7344 (3)	0.0366 (12)
H9A	0.2149	0.1748	0.6981	0.044*
C10	0.2441 (9)	0.1032 (4)	0.8694 (3)	0.0361 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0556 (8)	0.0504 (7)	0.0290 (6)	−0.0132 (7)	−0.0100 (6)	0.0072 (6)
O1	0.065 (3)	0.050 (2)	0.0326 (17)	0.019 (2)	0.0068 (19)	0.0024 (16)
O2	0.066 (3)	0.057 (2)	0.0233 (14)	0.020 (2)	−0.0041 (16)	0.0007 (15)
N1	0.060 (3)	0.052 (3)	0.029 (2)	−0.017 (3)	−0.002 (2)	0.0045 (19)
N2	0.061 (3)	0.049 (3)	0.0229 (19)	−0.002 (2)	−0.012 (2)	0.0026 (18)
N3	0.050 (3)	0.047 (2)	0.034 (2)	−0.007 (2)	−0.0074 (19)	0.001 (2)
C1	0.057 (4)	0.059 (3)	0.029 (2)	−0.010 (3)	−0.009 (3)	0.003 (2)
C2	0.052 (3)	0.030 (2)	0.028 (2)	0.001 (3)	−0.002 (2)	−0.0002 (19)
C3	0.056 (3)	0.039 (3)	0.030 (2)	−0.012 (2)	−0.012 (3)	0.004 (2)
C4	0.046 (3)	0.030 (2)	0.033 (2)	−0.011 (2)	−0.008 (2)	0.001 (2)
C5	0.043 (3)	0.034 (3)	0.046 (3)	−0.001 (2)	−0.012 (3)	0.007 (2)
C6	0.040 (3)	0.051 (3)	0.038 (3)	0.006 (3)	−0.001 (2)	−0.003 (2)
C7	0.046 (3)	0.041 (3)	0.030 (2)	−0.002 (3)	−0.003 (2)	0.004 (2)
C8	0.040 (3)	0.031 (2)	0.028 (2)	−0.002 (2)	−0.005 (2)	0.000 (2)
C9	0.049 (3)	0.031 (2)	0.029 (2)	0.001 (3)	0.000 (2)	−0.003 (2)
C10	0.041 (3)	0.037 (2)	0.031 (2)	0.000 (3)	0.000 (2)	0.001 (2)

Geometric parameters (Å, º)

S1—C2	1.760 (4)	C3—C4	1.524 (6)
S1—C3	1.818 (5)	C3—H3A	0.9900
O1—C10	1.220 (5)	C3—H3B	0.9900
O2—C10	1.317 (5)	C4—C5	1.384 (7)
O2—N1^i	2.707 (6)	C4—C9	1.390 (7)
O2—H2B	0.8400	C5—C6	1.396 (7)
N1—C1	1.338 (6)	C5—H5A	0.9500
N1—C2	1.352 (6)	C6—C7	1.381 (7)
N2—C1	1.314 (7)	C6—H6A	0.9500
N2—N3	1.373 (5)	C7—C8	1.383 (7)
N2—O1^ii	2.767 (5)	C7—H7A	0.9500
N2—H2A	0.8800	C8—C9	1.403 (6)
N3—C2	1.318 (6)	C8—C10	1.486 (7)
C1—H1A	0.9500	C9—H9A	0.9500
C2—S1—C3	101.3 (2)	H3A—C3—H3B	108.8
C10—O2—N1^i	116.2 (3)	C5—C4—C9	119.8 (4)
C10—O2—H2B	109.5	C5—C4—C3	119.7 (4)
N1^i—O2—H2B	12.0	C9—C4—C3	120.4 (5)
C1—N1—C2	102.0 (4)	C4—C5—C6	120.2 (5)
C1—N2—N3	110.9 (4)	C4—C5—H5A	119.9
C1—N2—O1^ii	131.2 (3)	C6—C5—H5A	119.9
N3—N2—O1^ii	117.9 (3)	C7—C6—C5	120.0 (5)
C1—N2—H2A	124.5	C7—C6—H6A	120.0
N3—N2—H2A	124.5	C5—C6—H6A	120.0
O1^ii—N2—H2A	6.7	C6—C7—C8	120.3 (4)
C2—N3—N2	100.8 (4)	C6—C7—H7A	119.8
N2—C1—N1	110.2 (5)	C8—C7—H7A	119.8
N2—C1—H1A	124.9	C7—C8—C9	119.7 (4)
N1—C1—H1A	124.9	C7—C8—C10	121.6 (4)
N3—C2—N1	116.2 (4)	C9—C8—C10	118.6 (4)
N3—C2—S1	124.1 (4)	C4—C9—C8	119.9 (5)
N1—C2—S1	119.7 (4)	C4—C9—H9A	120.0
C4—C3—S1	105.4 (3)	C8—C9—H9A	120.0
C4—C3—H3A	110.7	O1—C10—O2	122.3 (5)
S1—C3—H3A	110.7	O1—C10—C8	124.4 (4)
C4—C3—H3B	110.7	O2—C10—C8	113.2 (4)
S1—C3—H3B	110.7

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N1^i	0.84	1.89	2.707 (6)	163
N2—H2A···O1^ii	0.88	1.90	2.767 (5)	170

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, −z+1.