The title compound, C
10H
9N
5O
2·C
2H
6O, was synthesized by the reaction of 3-hydrazino-1
H-1,2,4-triazole with 2-hydroxybenzaldehyde in ethanol. The crystal structure involves intermolecular O—H
O, N—H
O and N—H
N hydrogen bonds; intramolecular O—H
N and N—H
N hydrogen bonds are also found.
Supporting information
CCDC reference: 270565
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.076
- wR factor = 0.229
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.00 Sigma
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.145
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.14
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C11 - C12 ... 1.35 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
3-[(2-Hydroxybenzylidene)hydrazinocarbonyl]-1
H-1,2,4-triazole ethanol
solvate
top
Crystal data top
C10H9N5O2·C2H6O | F(000) = 584 |
Mr = 277.29 | Dx = 1.344 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 950 reflections |
a = 15.554 (6) Å | θ = 4.9–42.9° |
b = 10.012 (4) Å | µ = 0.10 mm−1 |
c = 8.856 (4) Å | T = 293 K |
β = 96.217 (8)° | Block, colourless |
V = 1370.9 (10) Å3 | 0.50 × 0.35 × 0.11 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 2541 independent reflections |
Radiation source: fine-focus sealed tube | 1287 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.145 |
φ and ω scans | θmax = 25.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −18→18 |
Tmin = 0.959, Tmax = 0.989 | k = −9→12 |
6982 measured reflections | l = −10→10 |
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)] = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.229 | w = 1/[σ2(Fo2) + (0.0984P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.007 |
2541 reflections | Δρmax = 0.34 e Å−3 |
219 parameters | Δρmin = −0.39 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.002 (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 | |
O1 | 0.61846 (16) | 0.6390 (2) | 1.0638 (3) | 0.0609 (8) | |
O2 | 0.8122 (2) | 0.5507 (3) | 0.8000 (4) | 0.0767 (9) | |
O3 | 0.7508 (3) | 0.3950 (4) | 0.5182 (6) | 0.1539 (19) | |
H3A | 0.7707 | 0.4172 | 0.6041 | 0.231* | |
N1 | 0.67813 (19) | 0.8276 (3) | 0.9795 (4) | 0.0543 (8) | |
N2 | 0.73566 (18) | 0.7618 (3) | 0.8998 (3) | 0.0509 (8) | |
N3 | 0.50602 (18) | 0.7993 (3) | 1.2228 (4) | 0.0554 (9) | |
N4 | 0.57657 (18) | 0.9784 (3) | 1.1476 (4) | 0.0546 (8) | |
N5 | 0.51576 (19) | 1.0150 (3) | 1.2366 (4) | 0.0554 (9) | |
C1 | 0.6232 (2) | 0.7592 (4) | 1.0587 (4) | 0.0479 (9) | |
C2 | 0.5684 (2) | 0.8477 (3) | 1.1429 (4) | 0.0472 (9) | |
C3 | 0.4751 (3) | 0.9079 (4) | 1.2795 (5) | 0.0606 (11) | |
C4 | 0.7871 (2) | 0.8343 (4) | 0.8331 (4) | 0.0547 (10) | |
C5 | 0.8522 (2) | 0.7764 (4) | 0.7496 (4) | 0.0532 (10) | |
C6 | 0.9089 (3) | 0.8591 (5) | 0.6812 (5) | 0.0649 (11) | |
C7 | 0.9757 (3) | 0.8099 (6) | 0.6084 (5) | 0.0797 (13) | |
C8 | 0.9870 (3) | 0.6739 (6) | 0.6027 (6) | 0.0821 (15) | |
C9 | 0.9315 (3) | 0.5902 (6) | 0.6642 (5) | 0.0741 (13) | |
C10 | 0.8646 (2) | 0.6389 (4) | 0.7394 (4) | 0.0607 (10) | |
C11 | 0.7112 (6) | 0.2676 (8) | 0.5237 (10) | 0.159 (3) | |
H11A | 0.6640 | 0.2750 | 0.5865 | 0.191* | |
H11B | 0.6861 | 0.2452 | 0.4219 | 0.191* | |
C12 | 0.7619 (6) | 0.1649 (9) | 0.5767 (11) | 0.209 (5) | |
H12A | 0.7775 | 0.1758 | 0.6838 | 0.313* | |
H12B | 0.8132 | 0.1633 | 0.5255 | 0.313* | |
H12C | 0.7309 | 0.0825 | 0.5584 | 0.313* | |
H1 | 0.674 (3) | 0.911 (2) | 0.985 (5) | 0.076 (13)* | |
H2 | 0.776 (2) | 0.587 (4) | 0.852 (4) | 0.072 (14)* | |
H3 | 0.428 (2) | 0.909 (3) | 1.345 (4) | 0.060 (11)* | |
H4 | 0.783 (2) | 0.933 (4) | 0.838 (4) | 0.078 (12)* | |
H5 | 0.507 (2) | 1.097 (4) | 1.258 (4) | 0.063 (12)* | |
H6 | 0.897 (2) | 0.949 (4) | 0.693 (4) | 0.068 (12)* | |
H7 | 1.018 (2) | 0.864 (3) | 0.568 (4) | 0.074 (12)* | |
H8 | 1.035 (3) | 0.637 (4) | 0.555 (5) | 0.091 (14)* | |
H9 | 0.940 (3) | 0.494 (5) | 0.656 (5) | 0.089 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0664 (16) | 0.0349 (15) | 0.0816 (19) | 0.0006 (11) | 0.0093 (13) | −0.0036 (12) |
O2 | 0.094 (2) | 0.0462 (17) | 0.093 (2) | 0.0061 (16) | 0.0232 (19) | −0.0071 (15) |
O3 | 0.221 (5) | 0.072 (3) | 0.183 (4) | −0.003 (3) | 0.083 (4) | 0.017 (3) |
N1 | 0.0600 (19) | 0.0356 (18) | 0.069 (2) | 0.0014 (15) | 0.0135 (16) | −0.0027 (15) |
N2 | 0.0509 (18) | 0.0438 (18) | 0.0584 (19) | 0.0031 (13) | 0.0079 (15) | −0.0059 (14) |
N3 | 0.0568 (19) | 0.0348 (17) | 0.076 (2) | −0.0001 (13) | 0.0142 (16) | −0.0032 (15) |
N4 | 0.0545 (19) | 0.0365 (17) | 0.074 (2) | −0.0001 (13) | 0.0124 (16) | 0.0016 (14) |
N5 | 0.057 (2) | 0.0330 (19) | 0.077 (2) | 0.0036 (14) | 0.0141 (17) | 0.0008 (16) |
C1 | 0.046 (2) | 0.038 (2) | 0.058 (2) | −0.0003 (15) | 0.0004 (18) | −0.0020 (16) |
C2 | 0.0431 (19) | 0.038 (2) | 0.060 (2) | −0.0006 (15) | 0.0047 (17) | −0.0003 (16) |
C3 | 0.059 (2) | 0.039 (2) | 0.085 (3) | 0.0011 (17) | 0.018 (2) | 0.0003 (19) |
C4 | 0.056 (2) | 0.050 (2) | 0.058 (2) | 0.0060 (18) | 0.0049 (19) | −0.0051 (19) |
C5 | 0.053 (2) | 0.052 (2) | 0.054 (2) | 0.0063 (17) | 0.0026 (19) | −0.0030 (17) |
C6 | 0.065 (3) | 0.062 (3) | 0.068 (3) | 0.000 (2) | 0.008 (2) | −0.005 (2) |
C7 | 0.064 (3) | 0.103 (4) | 0.076 (3) | −0.003 (3) | 0.024 (2) | −0.005 (3) |
C8 | 0.068 (3) | 0.104 (4) | 0.076 (3) | 0.022 (3) | 0.014 (3) | −0.019 (3) |
C9 | 0.080 (3) | 0.071 (3) | 0.071 (3) | 0.024 (3) | 0.006 (3) | −0.015 (2) |
C10 | 0.062 (2) | 0.063 (3) | 0.056 (2) | 0.009 (2) | −0.002 (2) | −0.003 (2) |
C11 | 0.177 (7) | 0.112 (6) | 0.190 (8) | −0.010 (5) | 0.026 (6) | 0.024 (5) |
C12 | 0.260 (11) | 0.170 (8) | 0.206 (9) | 0.118 (8) | 0.067 (8) | 0.016 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.207 (4) | C4—H4 | 0.99 (4) |
O2—C10 | 1.351 (5) | C5—C10 | 1.394 (5) |
O2—H2 | 0.850 (19) | C5—C6 | 1.395 (5) |
O3—C11 | 1.419 (7) | C6—C7 | 1.372 (6) |
O3—H3A | 0.8200 | C6—H6 | 0.92 (4) |
N1—C1 | 1.348 (4) | C7—C8 | 1.375 (7) |
N1—N2 | 1.367 (4) | C7—H7 | 0.956 (19) |
N1—H1 | 0.837 (19) | C8—C9 | 1.358 (7) |
N2—C4 | 1.271 (5) | C8—H8 | 0.97 (5) |
N3—C3 | 1.311 (4) | C9—C10 | 1.384 (6) |
N3—C2 | 1.351 (4) | C9—H9 | 0.97 (5) |
N4—C2 | 1.315 (4) | C11—C12 | 1.348 (9) |
N4—N5 | 1.346 (4) | C11—H11A | 0.9700 |
N5—C3 | 1.321 (5) | C11—H11B | 0.9700 |
N5—H5 | 0.85 (4) | C12—H12A | 0.9600 |
C1—C2 | 1.485 (5) | C12—H12B | 0.9600 |
C3—H3 | 0.99 (4) | C12—H12C | 0.9600 |
C4—C5 | 1.439 (5) | | |
| | | |
C10—O2—H2 | 113 (3) | C7—C6—H6 | 125 (2) |
C11—O3—H3A | 109.5 | C5—C6—H6 | 113 (2) |
C1—N1—N2 | 120.7 (3) | C6—C7—C8 | 118.7 (5) |
C1—N1—H1 | 115 (3) | C6—C7—H7 | 124 (3) |
N2—N1—H1 | 124 (3) | C8—C7—H7 | 117 (3) |
C4—N2—N1 | 116.4 (3) | C9—C8—C7 | 120.4 (5) |
C3—N3—C2 | 102.5 (3) | C9—C8—H8 | 119 (3) |
C2—N4—N5 | 102.6 (3) | C7—C8—H8 | 120 (3) |
C3—N5—N4 | 109.6 (3) | C8—C9—C10 | 121.3 (5) |
C3—N5—H5 | 129 (3) | C8—C9—H9 | 118 (3) |
N4—N5—H5 | 122 (3) | C10—C9—H9 | 120 (3) |
O1—C1—N1 | 124.8 (3) | O2—C10—C9 | 118.6 (4) |
O1—C1—C2 | 122.3 (3) | O2—C10—C5 | 121.7 (4) |
N1—C1—C2 | 112.9 (3) | C9—C10—C5 | 119.7 (4) |
N4—C2—N3 | 114.4 (3) | C12—C11—O3 | 117.3 (8) |
N4—C2—C1 | 123.4 (3) | C12—C11—H11A | 108.0 |
N3—C2—C1 | 122.2 (3) | O3—C11—H11A | 108.0 |
N3—C3—N5 | 110.9 (4) | C12—C11—H11B | 108.0 |
N3—C3—H3 | 124 (2) | O3—C11—H11B | 108.0 |
N5—C3—H3 | 125 (2) | H11A—C11—H11B | 107.2 |
N2—C4—C5 | 121.5 (4) | C11—C12—H12A | 109.5 |
N2—C4—H4 | 120 (2) | C11—C12—H12B | 109.5 |
C5—C4—H4 | 119 (2) | H12A—C12—H12B | 109.5 |
C10—C5—C6 | 117.4 (4) | C11—C12—H12C | 109.5 |
C10—C5—C4 | 122.7 (4) | H12A—C12—H12C | 109.5 |
C6—C5—C4 | 119.8 (4) | H12B—C12—H12C | 109.5 |
C7—C6—C5 | 122.5 (5) | | |
| | | |
C1—N1—N2—C4 | −177.5 (3) | N1—N2—C4—C5 | 178.0 (3) |
C2—N4—N5—C3 | −0.1 (4) | N2—C4—C5—C10 | −1.5 (5) |
N2—N1—C1—O1 | −1.6 (5) | N2—C4—C5—C6 | −178.4 (3) |
N2—N1—C1—C2 | 177.6 (3) | C10—C5—C6—C7 | −1.2 (6) |
N5—N4—C2—N3 | 0.3 (4) | C4—C5—C6—C7 | 175.8 (4) |
N5—N4—C2—C1 | −179.2 (3) | C5—C6—C7—C8 | 0.1 (7) |
C3—N3—C2—N4 | −0.3 (4) | C6—C7—C8—C9 | 1.9 (7) |
C3—N3—C2—C1 | 179.2 (3) | C7—C8—C9—C10 | −2.7 (7) |
O1—C1—C2—N4 | 175.1 (3) | C8—C9—C10—O2 | −179.1 (4) |
N1—C1—C2—N4 | −4.1 (5) | C8—C9—C10—C5 | 1.5 (6) |
O1—C1—C2—N3 | −4.3 (5) | C6—C5—C10—O2 | −178.9 (3) |
N1—C1—C2—N3 | 176.4 (3) | C4—C5—C10—O2 | 4.2 (5) |
C2—N3—C3—N5 | 0.2 (4) | C6—C5—C10—C9 | 0.4 (5) |
N4—N5—C3—N3 | −0.1 (5) | C4—C5—C10—C9 | −176.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N3i | 0.85 (4) | 2.05 (4) | 2.893 (5) | 171 (4) |
N1—H1···O3ii | 0.84 (2) | 2.28 (3) | 3.005 (5) | 145 (4) |
O2—H2···N2 | 0.85 (2) | 1.92 (3) | 2.625 (4) | 140 (4) |
N1—H1···N4 | 0.84 (2) | 2.30 (4) | 2.739 (4) | 113 (3) |
O3—H3A···O2 | 0.82 | 2.23 | 3.009 (6) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+5/2; (ii) x, −y+3/2, z+1/2. |