3-[(2-Hydro­xy­benzyl­idene)­hydrazino­carbonyl]-1H-1,2,4-triazole ethanol solvate

The title compound, C₁₀H₉N₅O₂·C₂H₆O, was synthesized by the reaction of 3-hydrazino-1H-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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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]-1H-1,2,4-triazole ethanol solvate

Crystal data

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) Å^3	0.50 × 0.35 × 0.11 mm
Z = 4

Data collection

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

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)] = 0.076	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.0984P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.002 (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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3^i	0.85 (4)	2.05 (4)	2.893 (5)	171 (4)
N1—H1···O3^ii	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.