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The title compound, C
10H
9N
3O
2S, crystallizes in the orthorhombic non-centrosymmetric space group
P2
12
12
1. The molecules are linked into a three-dimensional network through O—H
N and N—H
O hydrogen bonds and weak S
O interactions.
Supporting information
CCDC reference: 239260
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-(1
H-1,2,4-Triazole-3-ylsulfanylmethyl)benzoic acid
top
Crystal data top
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) Å3 | Needle, colorless |
Z = 4 | 0.20 × 0.10 × 0.08 mm |
F(000) = 488 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0275P)2 + 1.1042P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—N1i | 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—O1ii | 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—N1i | 116.2 (3) | C5—C4—C9 | 119.8 (4) |
C10—O2—H2B | 109.5 | C5—C4—C3 | 119.7 (4) |
N1i—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—O1ii | 131.2 (3) | C6—C5—H5A | 119.9 |
N3—N2—O1ii | 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 |
O1ii—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2B···N1i | 0.84 | 1.89 | 2.707 (6) | 163 |
N2—H2A···O1ii | 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. |
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