Molecules of the title compound, C
12H
11N
3O
3, are linked into zigzag chains by O—H
N hydrogen bonds. The crystal structure is further stabilized by π–π stacking interactions.
Supporting information
CCDC reference: 298370
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.074
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 5.42 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
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 27.92
From the CIF: _reflns_number_total 1569
Count of symmetry unique reflns 1619
Completeness (_total/calc) 96.91%
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
2 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2000); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003).
2-[(
E)-(3,5-dimethylisoxazol-4-yl)diazenyl]benzoic acid
top
Crystal data top
C12H11N3O3 | F(000) = 512 |
Mr = 245.24 | Dx = 1.398 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 999 reflections |
a = 7.355 (1) Å | θ = 2.3–27.9° |
b = 11.6182 (15) Å | µ = 0.10 mm−1 |
c = 13.6335 (17) Å | T = 298 K |
V = 1165.0 (3) Å3 | Polyhedron, orange |
Z = 4 | 0.26 × 0.20 × 0.18 mm |
Data collection top
Bruker CCD area-detector diffractometer | Rint = 0.073 |
φ and ω scans | θmax = 27.9°, θmin = 2.3° |
8600 measured reflections | h = −9→9 |
1569 independent reflections | k = −14→15 |
945 reflections with I > 2σ(I) | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0217P)2] where P = (Fo2 + 2Fc2)/3 |
1569 reflections | (Δ/σ)max = 0.019 |
165 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
O1 | −0.0456 (3) | 0.43833 (14) | 0.58562 (13) | 0.0644 (8) | |
O2 | 0.0666 (4) | 0.60320 (17) | 0.53653 (15) | 0.0937 (10) | |
O3 | 0.1131 (3) | −0.07335 (15) | 0.66792 (15) | 0.0638 (8) | |
N1 | 0.1334 (3) | 0.2583 (2) | 0.51087 (15) | 0.0444 (8) | |
N2 | 0.0938 (3) | 0.15464 (18) | 0.49671 (15) | 0.0464 (8) | |
N3 | 0.1450 (3) | 0.0195 (2) | 0.73388 (16) | 0.0580 (9) | |
C1 | 0.1269 (4) | 0.3258 (2) | 0.42316 (19) | 0.0425 (9) | |
C2 | 0.1738 (4) | 0.2786 (2) | 0.3325 (2) | 0.0527 (11) | |
C3 | 0.1851 (4) | 0.3466 (3) | 0.2505 (2) | 0.0598 (11) | |
C4 | 0.1504 (4) | 0.4629 (3) | 0.2576 (2) | 0.0613 (11) | |
C5 | 0.1059 (4) | 0.5106 (2) | 0.34606 (19) | 0.0544 (11) | |
C6 | 0.0931 (4) | 0.4433 (2) | 0.42999 (19) | 0.0433 (10) | |
C7 | 0.0404 (4) | 0.5038 (2) | 0.5224 (2) | 0.0503 (11) | |
C8 | 0.1733 (4) | 0.2247 (2) | 0.73059 (19) | 0.0621 (11) | |
C9 | 0.1443 (4) | 0.1129 (2) | 0.6812 (2) | 0.0461 (10) | |
C10 | 0.1099 (4) | 0.0867 (2) | 0.5813 (2) | 0.0410 (9) | |
C11 | 0.0908 (4) | −0.0285 (2) | 0.5772 (2) | 0.0513 (11) | |
C12 | 0.0560 (5) | −0.1113 (2) | 0.4975 (2) | 0.0733 (13) | |
H1 | −0.07080 | 0.47610 | 0.63460 | 0.0970* | |
H2 | 0.19760 | 0.20020 | 0.32770 | 0.0630* | |
H3 | 0.21600 | 0.31430 | 0.19040 | 0.0720* | |
H4 | 0.15730 | 0.50900 | 0.20200 | 0.0740* | |
H5 | 0.08380 | 0.58930 | 0.35010 | 0.0650* | |
H8A | 0.16880 | 0.21400 | 0.80040 | 0.0930* | |
H8B | 0.07990 | 0.27770 | 0.71100 | 0.0930* | |
H8C | 0.29000 | 0.25500 | 0.71250 | 0.0930* | |
H12A | 0.14570 | −0.17130 | 0.49950 | 0.1100* | |
H12B | 0.06260 | −0.07240 | 0.43550 | 0.1100* | |
H12C | −0.06280 | −0.14420 | 0.50550 | 0.1100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0950 (16) | 0.0497 (12) | 0.0484 (12) | −0.0074 (11) | 0.0158 (12) | −0.0041 (10) |
O2 | 0.159 (2) | 0.0401 (13) | 0.0819 (16) | −0.0203 (16) | 0.0253 (16) | −0.0065 (12) |
O3 | 0.0885 (17) | 0.0466 (12) | 0.0562 (13) | 0.0004 (12) | 0.0064 (13) | 0.0130 (10) |
N1 | 0.0516 (15) | 0.0399 (12) | 0.0418 (13) | 0.0029 (13) | 0.0034 (12) | 0.0047 (11) |
N2 | 0.0500 (15) | 0.0418 (14) | 0.0475 (14) | 0.0027 (12) | 0.0049 (12) | 0.0049 (12) |
N3 | 0.0762 (18) | 0.0529 (15) | 0.0450 (14) | 0.0055 (15) | 0.0068 (14) | 0.0071 (14) |
C1 | 0.0430 (17) | 0.0449 (16) | 0.0396 (16) | −0.0027 (14) | −0.0013 (16) | 0.0056 (14) |
C2 | 0.061 (2) | 0.0529 (18) | 0.0441 (18) | 0.0084 (16) | 0.0078 (16) | 0.0057 (16) |
C3 | 0.071 (2) | 0.066 (2) | 0.0423 (19) | 0.0038 (18) | 0.0104 (17) | 0.0047 (17) |
C4 | 0.074 (2) | 0.064 (2) | 0.0459 (19) | −0.0035 (19) | 0.0012 (18) | 0.0194 (17) |
C5 | 0.065 (2) | 0.0479 (18) | 0.0504 (18) | −0.0058 (18) | 0.0021 (17) | 0.0118 (16) |
C6 | 0.0460 (18) | 0.0395 (16) | 0.0444 (17) | −0.0052 (15) | 0.0000 (15) | 0.0039 (14) |
C7 | 0.063 (2) | 0.0389 (18) | 0.0490 (17) | −0.0065 (16) | −0.0005 (16) | 0.0035 (15) |
C8 | 0.076 (2) | 0.058 (2) | 0.0524 (19) | 0.0028 (18) | −0.0030 (17) | −0.0035 (17) |
C9 | 0.0468 (18) | 0.0449 (17) | 0.0466 (18) | 0.0050 (16) | 0.0080 (16) | 0.0061 (15) |
C10 | 0.0455 (17) | 0.0367 (16) | 0.0409 (16) | 0.0032 (14) | 0.0035 (16) | 0.0068 (14) |
C11 | 0.059 (2) | 0.0505 (18) | 0.0444 (17) | 0.0019 (17) | 0.0039 (17) | 0.0072 (16) |
C12 | 0.103 (3) | 0.0500 (18) | 0.067 (2) | −0.007 (2) | −0.002 (2) | −0.0032 (18) |
Geometric parameters (Å, º) top
O3—N3 | 1.424 (3) | C5—C6 | 1.389 (4) |
O3—C11 | 1.352 (3) | C6—C7 | 1.494 (4) |
O1—H1 | 0.8200 | C1—C6 | 1.391 (3) |
N3—C9 | 1.301 (3) | O1—C7 | 1.312 (3) |
C8—C9 | 1.479 (3) | O2—C7 | 1.187 (3) |
C9—C10 | 1.418 (4) | C2—H2 | 0.9300 |
C10—C11 | 1.347 (3) | C3—H3 | 0.9300 |
C11—C12 | 1.474 (4) | C4—H4 | 0.9300 |
N2—C10 | 1.403 (3) | C5—H5 | 0.9300 |
N1—N2 | 1.254 (3) | C8—H8A | 0.9600 |
N1—C1 | 1.431 (3) | C8—H8B | 0.9600 |
C1—C2 | 1.396 (4) | C8—H8C | 0.9600 |
C2—C3 | 1.372 (4) | C12—H12A | 0.9600 |
C3—C4 | 1.379 (5) | C12—H12B | 0.9600 |
C4—C5 | 1.367 (4) | C12—H12C | 0.9600 |
| | | |
O1···N1 | 2.673 (3) | C8···N1 | 3.035 (3) |
O1···N2i | 3.076 (3) | C9···C3i | 3.535 (4) |
O1···C10i | 3.418 (4) | C10···C6v | 3.574 (4) |
O1···N3ii | 2.735 (3) | C10···O1v | 3.418 (4) |
O2···C12iii | 3.360 (3) | C11···C7v | 3.586 (4) |
O1···H8B | 2.6900 | C12···O2vii | 3.360 (3) |
O1···H2i | 2.7500 | C2···H8Ci | 2.9200 |
O2···H5 | 2.5500 | C4···H12Bviii | 3.0900 |
O2···H12Aiii | 2.7300 | C9···H1vi | 3.0200 |
O2···H3iv | 2.8100 | H1···O3ii | 2.7700 |
O2···H12Cv | 2.8300 | H1···N3ii | 1.9400 |
O3···H1vi | 2.7700 | H1···C9ii | 3.0200 |
O3···H8Bvi | 2.7800 | H2···N2 | 2.4800 |
N1···O1 | 2.673 (3) | H2···O1v | 2.7500 |
N1···C8 | 3.035 (3) | H3···O2ix | 2.8100 |
N2···O1v | 3.076 (3) | H5···O2 | 2.5500 |
N3···O1vi | 2.735 (3) | H8B···O1 | 2.6900 |
N1···H8B | 2.7700 | H8B···N1 | 2.7700 |
N2···H12B | 2.7800 | H8B···O3ii | 2.7800 |
N2···H2 | 2.4800 | H8C···C2v | 2.9200 |
N3···H1vi | 1.9400 | H12A···O2vii | 2.7300 |
C3···C9v | 3.535 (4) | H12B···N2 | 2.7800 |
C6···C10i | 3.574 (4) | H12B···C4x | 3.0900 |
C7···C11i | 3.586 (4) | H12C···O2i | 2.8300 |
| | | |
N3—O3—C11 | 107.80 (18) | O3—C11—C12 | 116.4 (2) |
C7—O1—H1 | 109.00 | C10—C11—C12 | 134.2 (3) |
N2—N1—C1 | 113.0 (2) | O3—C11—C10 | 109.4 (2) |
N1—N2—C10 | 113.2 (2) | C1—C2—H2 | 120.00 |
O3—N3—C9 | 106.4 (2) | C3—C2—H2 | 120.00 |
N1—C1—C6 | 119.2 (2) | C2—C3—H3 | 120.00 |
C2—C1—C6 | 119.3 (2) | C4—C3—H3 | 120.00 |
N1—C1—C2 | 121.1 (2) | C3—C4—H4 | 120.00 |
C1—C2—C3 | 120.7 (2) | C5—C4—H4 | 120.00 |
C2—C3—C4 | 119.8 (3) | C4—C5—H5 | 120.00 |
C3—C4—C5 | 120.2 (3) | C6—C5—H5 | 120.00 |
C4—C5—C6 | 121.0 (2) | C9—C8—H8A | 109.00 |
C1—C6—C7 | 124.4 (2) | C9—C8—H8B | 109.00 |
C5—C6—C7 | 116.6 (2) | C9—C8—H8C | 110.00 |
C1—C6—C5 | 119.0 (2) | H8A—C8—H8B | 110.00 |
O1—C7—O2 | 122.4 (3) | H8A—C8—H8C | 109.00 |
O1—C7—C6 | 114.0 (2) | H8B—C8—H8C | 109.00 |
O2—C7—C6 | 123.6 (3) | C11—C12—H12A | 109.00 |
N3—C9—C8 | 118.7 (2) | C11—C12—H12B | 109.00 |
N3—C9—C10 | 110.6 (2) | C11—C12—H12C | 110.00 |
C8—C9—C10 | 130.7 (2) | H12A—C12—H12B | 109.00 |
N2—C10—C11 | 121.1 (2) | H12A—C12—H12C | 109.00 |
C9—C10—C11 | 105.8 (2) | H12B—C12—H12C | 109.00 |
N2—C10—C9 | 133.2 (2) | | |
| | | |
N3—O3—C11—C10 | 1.1 (3) | C2—C3—C4—C5 | 0.4 (4) |
N3—O3—C11—C12 | 180.0 (2) | C3—C4—C5—C6 | −0.6 (5) |
C11—O3—N3—C9 | −1.3 (3) | C4—C5—C6—C1 | 0.2 (4) |
N2—N1—C1—C2 | −33.5 (4) | C4—C5—C6—C7 | −179.0 (3) |
N2—N1—C1—C6 | 153.8 (3) | C1—C6—C7—O2 | 155.4 (3) |
C1—N1—N2—C10 | 176.6 (2) | C1—C6—C7—O1 | −27.6 (4) |
N1—N2—C10—C11 | −173.1 (3) | C5—C6—C7—O1 | 151.5 (3) |
N1—N2—C10—C9 | 7.3 (4) | C5—C6—C7—O2 | −25.5 (4) |
O3—N3—C9—C8 | 179.6 (2) | N3—C9—C10—N2 | 179.3 (3) |
O3—N3—C9—C10 | 0.9 (3) | C8—C9—C10—C11 | −178.8 (3) |
N1—C1—C2—C3 | −173.3 (3) | N3—C9—C10—C11 | −0.3 (3) |
N1—C1—C6—C7 | −7.7 (4) | C8—C9—C10—N2 | 0.9 (6) |
C2—C1—C6—C5 | 0.4 (4) | N2—C10—C11—O3 | 179.8 (2) |
C2—C1—C6—C7 | 179.5 (3) | C9—C10—C11—C12 | −179.1 (3) |
N1—C1—C6—C5 | 173.3 (3) | N2—C10—C11—C12 | 1.2 (5) |
C6—C1—C2—C3 | −0.6 (4) | C9—C10—C11—O3 | −0.6 (3) |
C1—C2—C3—C4 | 0.2 (4) | | |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) x, y+1, z; (iv) −x+1/2, −y+1, z+1/2; (v) x+1/2, −y+1/2, −z+1; (vi) −x, y−1/2, −z+3/2; (vii) x, y−1, z; (viii) −x, y+1/2, −z+1/2; (ix) −x+1/2, −y+1, z−1/2; (x) −x, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N3ii | 0.82 | 1.94 | 2.735 (3) | 163 |
Symmetry code: (ii) −x, y+1/2, −z+3/2. |