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The title compound, C11H11N5O3, was synthesized by the reaction of 3-(1H)-1,2,4-triazole hydrazine with 4-hydroxy-3-methoxy­benz­aldehyde in ethanol. In the crystal structure, intermolecular N—H...O, O—H...N and N—H...N hydrogen bonds are observed. An intramolecular O—H...O hydrogen bond is also found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034269/is6028sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034269/is6028Isup2.hkl
Contains datablock I

CCDC reference: 264101

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.140
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.45 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.07 PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C1 .. 2.97 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H11 N5 O3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SHELXTL (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-[(4-Hydroxy-3-methoxyphenyl)methylenehydrazinocarbonyl]-(1H)-1,2,4-Triazole top
Crystal data top
C11H11N5O3Z = 4
Mr = 261.25F(000) = 544
Triclinic, P1Dx = 1.466 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.473 (1) ÅCell parameters from 25 reflections
b = 14.772 (5) Åθ = 9.8–14.8°
c = 18.263 (2) ŵ = 0.11 mm1
α = 79.38 (2)°T = 293 K
β = 88.78 (1)°Spiculate, brown
γ = 86.33 (2)°0.40 × 0.20 × 0.10 mm
V = 1183.6 (5) Å3
Data collection top
Bruker APEX area-detector
diffractometer
4271 independent reflections
Radiation source: fine-focus sealed tube2357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.2°, θmin = 1.1°
Absorption correction: multi-scan
SADABS (Bruker, 2002)
h = 55
Tmin = 0.957, Tmax = 0.989k = 171
4819 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0831P)2 + 0.0981P]
where P = (Fo2 + 2Fc2)/3
4271 reflections(Δ/σ)max < 0.001
347 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
O11.1420 (4)1.25562 (13)0.05702 (9)0.0515 (5)
O20.0449 (4)0.87349 (13)0.09108 (10)0.0538 (5)
O30.2375 (4)0.80654 (13)0.21688 (11)0.0541 (5)
H30.25070.79240.17550.081*
O41.0455 (5)0.55491 (14)0.26267 (10)0.0627 (6)
O51.2849 (5)0.63936 (13)0.60994 (10)0.0599 (6)
O61.0800 (5)0.79185 (15)0.65774 (10)0.0662 (6)
H6A1.18450.74720.67840.099*
N11.5371 (5)1.38568 (14)0.11372 (11)0.0415 (5)
N21.6889 (5)1.42595 (15)0.16499 (12)0.0452 (6)
H21.82281.47070.15480.054*
N31.3951 (5)1.32054 (16)0.22994 (12)0.0491 (6)
N40.9696 (4)1.20748 (14)0.17482 (11)0.0390 (5)
H40.98431.21650.22000.047*
N50.7621 (4)1.14090 (14)0.15822 (11)0.0384 (5)
N60.8693 (5)0.56851 (15)0.11694 (11)0.0454 (6)
N70.5247 (5)0.66398 (16)0.06080 (12)0.0495 (6)
H70.40830.69220.02590.059*
N80.5261 (5)0.68206 (15)0.13039 (12)0.0466 (6)
N90.7068 (5)0.66888 (15)0.28114 (11)0.0471 (6)
H90.55430.70410.26370.057*
N100.8111 (5)0.67119 (15)0.35077 (11)0.0456 (6)
C11.6040 (6)1.38727 (19)0.23285 (15)0.0509 (8)
H11.68001.40440.27640.061*
C21.3611 (5)1.32289 (17)0.15598 (13)0.0366 (6)
C31.1496 (5)1.25877 (17)0.12317 (14)0.0367 (6)
C40.6135 (5)1.10045 (17)0.21522 (14)0.0387 (6)
H4A0.65091.11990.26030.046*
C50.3885 (5)1.02525 (16)0.21296 (14)0.0376 (6)
C60.2337 (6)0.98840 (18)0.27753 (14)0.0444 (7)
H60.27121.01270.32060.053*
C70.0234 (6)0.91548 (19)0.27804 (15)0.0461 (7)
H7A0.08070.89100.32150.055*
C80.0327 (6)0.87908 (17)0.21520 (14)0.0407 (6)
C90.1228 (5)0.91620 (17)0.14934 (14)0.0400 (6)
C100.3300 (5)0.98910 (17)0.14860 (14)0.0408 (6)
H100.43151.01440.10500.049*
C110.2320 (7)0.8953 (2)0.02675 (16)0.0549 (8)
H11A0.43520.88300.04110.082*
H11B0.16470.85800.00900.082*
H11C0.22130.95930.00500.082*
C120.7257 (6)0.5973 (2)0.05348 (15)0.0500 (7)
H120.76170.57370.01010.060*
C130.7403 (5)0.62222 (16)0.16241 (13)0.0380 (6)
C140.8436 (6)0.61144 (18)0.24034 (14)0.0430 (7)
C150.6881 (6)0.73314 (19)0.38260 (15)0.0492 (7)
H150.53130.77110.35910.059*
C160.7860 (6)0.74648 (19)0.45516 (14)0.0464 (7)
C170.6807 (7)0.8230 (2)0.48381 (16)0.0598 (9)
H170.54070.86510.45720.072*
C180.7805 (7)0.8378 (2)0.55104 (16)0.0619 (9)
H180.70950.89000.56930.074*
C190.9853 (7)0.7756 (2)0.59169 (14)0.0510 (7)
C201.0870 (6)0.69655 (19)0.56467 (14)0.0459 (7)
C210.9915 (6)0.68308 (18)0.49643 (14)0.0453 (7)
H211.06450.63140.47770.054*
C221.3787 (8)0.55363 (19)0.58878 (17)0.0612 (9)
H22A1.20780.51790.58720.092*
H22B1.51900.52020.62450.092*
H22C1.47250.56510.54050.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0551 (12)0.0617 (12)0.0355 (11)0.0325 (10)0.0105 (8)0.0141 (9)
O20.0540 (12)0.0607 (12)0.0464 (11)0.0349 (10)0.0128 (9)0.0205 (9)
O30.0511 (11)0.0511 (12)0.0549 (12)0.0344 (9)0.0128 (9)0.0075 (9)
O40.0745 (14)0.0651 (13)0.0453 (11)0.0459 (11)0.0243 (10)0.0160 (10)
O50.0819 (15)0.0530 (12)0.0442 (11)0.0336 (11)0.0247 (10)0.0176 (9)
O60.0928 (16)0.0656 (14)0.0402 (11)0.0406 (12)0.0230 (10)0.0229 (10)
N10.0427 (12)0.0399 (12)0.0405 (12)0.0202 (10)0.0108 (10)0.0101 (10)
N20.0448 (13)0.0453 (13)0.0448 (13)0.0264 (11)0.0128 (10)0.0153 (11)
N30.0553 (14)0.0541 (14)0.0366 (12)0.0317 (11)0.0143 (10)0.0149 (10)
N40.0391 (12)0.0444 (12)0.0328 (11)0.0242 (10)0.0096 (9)0.0134 (9)
N50.0365 (12)0.0377 (12)0.0395 (12)0.0207 (9)0.0078 (9)0.0103 (9)
N60.0511 (14)0.0476 (13)0.0370 (12)0.0189 (11)0.0141 (10)0.0126 (10)
N70.0515 (14)0.0559 (14)0.0375 (13)0.0180 (11)0.0214 (10)0.0039 (11)
N80.0468 (13)0.0473 (14)0.0428 (13)0.0182 (11)0.0147 (10)0.0063 (10)
N90.0506 (14)0.0526 (14)0.0383 (12)0.0260 (11)0.0187 (10)0.0168 (10)
N100.0528 (14)0.0473 (13)0.0370 (12)0.0160 (11)0.0146 (10)0.0132 (10)
C10.0589 (18)0.0555 (17)0.0377 (15)0.0302 (14)0.0124 (13)0.0166 (13)
C20.0358 (13)0.0389 (14)0.0347 (13)0.0159 (11)0.0127 (10)0.0101 (11)
C30.0344 (13)0.0391 (14)0.0359 (14)0.0161 (11)0.0093 (10)0.0101 (11)
C40.0372 (14)0.0411 (14)0.0377 (13)0.0142 (12)0.0060 (11)0.0120 (11)
C50.0324 (13)0.0341 (13)0.0436 (14)0.0138 (11)0.0084 (11)0.0044 (11)
C60.0452 (15)0.0493 (16)0.0372 (14)0.0189 (13)0.0101 (12)0.0103 (12)
C70.0427 (15)0.0473 (15)0.0436 (15)0.0195 (12)0.0153 (12)0.0020 (12)
C80.0362 (14)0.0352 (14)0.0468 (15)0.0164 (11)0.0073 (11)0.0023 (12)
C90.0343 (14)0.0410 (15)0.0435 (14)0.0141 (12)0.0052 (11)0.0098 (12)
C100.0374 (14)0.0437 (15)0.0391 (14)0.0177 (12)0.0105 (11)0.0072 (12)
C110.0596 (18)0.0584 (18)0.0479 (16)0.0210 (15)0.0124 (14)0.0199 (14)
C120.0581 (18)0.0536 (17)0.0370 (15)0.0178 (14)0.0129 (12)0.0114 (13)
C130.0389 (14)0.0349 (13)0.0391 (14)0.0127 (11)0.0098 (11)0.0075 (11)
C140.0462 (15)0.0410 (15)0.0399 (14)0.0175 (13)0.0120 (12)0.0085 (12)
C150.0552 (18)0.0514 (17)0.0401 (15)0.0205 (14)0.0151 (13)0.0123 (13)
C160.0512 (16)0.0504 (16)0.0369 (14)0.0164 (13)0.0077 (12)0.0118 (12)
C170.071 (2)0.0611 (19)0.0453 (16)0.0347 (16)0.0186 (14)0.0165 (14)
C180.079 (2)0.0571 (18)0.0502 (17)0.0366 (16)0.0153 (15)0.0239 (14)
C190.0641 (19)0.0543 (17)0.0343 (14)0.0209 (14)0.0089 (12)0.0148 (13)
C200.0545 (17)0.0463 (15)0.0350 (14)0.0163 (13)0.0090 (12)0.0084 (12)
C210.0530 (17)0.0431 (15)0.0388 (15)0.0153 (13)0.0050 (12)0.0107 (12)
C220.079 (2)0.0465 (17)0.0573 (18)0.0255 (16)0.0188 (16)0.0155 (14)
Geometric parameters (Å, º) top
O1—C31.217 (3)C2—C31.490 (3)
O2—C91.362 (3)C4—C51.456 (3)
O2—C111.432 (3)C4—H4A0.9300
O3—C81.361 (3)C5—C61.384 (3)
O3—H30.8200C5—C101.391 (4)
O4—C141.213 (3)C6—C71.383 (3)
O5—C201.363 (3)C6—H60.9300
O5—C221.427 (3)C7—C81.366 (4)
O6—C191.354 (3)C7—H7A0.9300
O6—H6A0.8200C8—C91.405 (3)
N1—C21.321 (3)C9—C101.373 (3)
N1—N21.348 (3)C10—H100.9300
N2—C11.318 (3)C11—H11A0.9599
N2—H20.8600C11—H11B0.9599
N3—C11.322 (3)C11—H11C0.9599
N3—C21.350 (3)C12—H120.9300
N4—C31.343 (3)C13—C141.483 (3)
N4—N51.379 (3)C15—C161.456 (4)
N4—H40.8600C15—H150.9300
N5—C41.277 (3)C16—C171.384 (4)
N6—C121.324 (3)C16—C211.396 (3)
N6—C131.348 (3)C17—C181.374 (4)
N7—C121.314 (3)C17—H170.9300
N7—N81.346 (3)C18—C191.380 (4)
N7—H70.8600C18—H180.9300
N8—C131.329 (3)C19—C201.396 (4)
N9—C141.341 (3)C20—C211.378 (4)
N9—N101.371 (3)C21—H210.9300
N9—H90.8600C22—H22A0.9599
N10—C151.263 (3)C22—H22B0.9599
C1—H10.9300C22—H22C0.9599
C9—O2—C11116.84 (18)O2—C9—C8113.8 (2)
C8—O3—H3109.5C10—C9—C8119.6 (2)
C20—O5—C22117.4 (2)C9—C10—C5120.2 (2)
C19—O6—H6A109.5C9—C10—H10119.9
C2—N1—N2101.80 (19)C5—C10—H10119.9
C1—N2—N1110.72 (19)O2—C11—H11A109.5
C1—N2—H2124.6O2—C11—H11B109.5
N1—N2—H2124.6H11A—C11—H11B109.5
C1—N3—C2102.6 (2)O2—C11—H11C109.5
C3—N4—N5122.5 (2)H11A—C11—H11C109.5
C3—N4—H4118.7H11B—C11—H11C109.5
N5—N4—H4118.7N7—C12—N6110.1 (2)
C4—N5—N4112.4 (2)N7—C12—H12125.0
C12—N6—C13103.1 (2)N6—C12—H12125.0
C12—N7—N8110.7 (2)N8—C13—N6114.0 (2)
C12—N7—H7124.6N8—C13—C14126.3 (2)
N8—N7—H7124.6N6—C13—C14119.8 (2)
C13—N8—N7102.17 (19)O4—C14—N9124.3 (2)
C14—N9—N10119.65 (19)O4—C14—C13119.9 (2)
C14—N9—H9120.2N9—C14—C13115.7 (2)
N10—N9—H9120.2N10—C15—C16121.6 (2)
C15—N10—N9115.6 (2)N10—C15—H15119.2
N2—C1—N3110.1 (2)C16—C15—H15119.2
N2—C1—H1125.0C17—C16—C21118.9 (2)
N3—C1—H1125.0C17—C16—C15120.5 (2)
N1—C2—N3114.7 (2)C21—C16—C15120.6 (2)
N1—C2—C3121.6 (2)C18—C17—C16120.8 (3)
N3—C2—C3123.7 (2)C18—C17—H17119.6
O1—C3—N4125.1 (2)C16—C17—H17119.6
O1—C3—C2122.9 (2)C17—C18—C19120.4 (3)
N4—C3—C2111.9 (2)C17—C18—H18119.8
N5—C4—C5123.1 (2)C19—C18—H18119.8
N5—C4—H4A118.4O6—C19—C18119.2 (2)
C5—C4—H4A118.4O6—C19—C20121.3 (2)
C6—C5—C10119.8 (2)C18—C19—C20119.5 (2)
C6—C5—C4118.3 (2)O5—C20—C21125.7 (2)
C10—C5—C4121.9 (2)O5—C20—C19114.5 (2)
C7—C6—C5120.0 (2)C21—C20—C19119.9 (2)
C7—C6—H6120.0C20—C21—C16120.4 (2)
C5—C6—H6120.0C20—C21—H21119.8
C8—C7—C6120.5 (2)C16—C21—H21119.8
C8—C7—H7A119.8O5—C22—H22A109.5
C6—C7—H7A119.8O5—C22—H22B109.5
O3—C8—C7119.8 (2)H22A—C22—H22B109.5
O3—C8—C9120.3 (2)O5—C22—H22C109.5
C7—C8—C9119.9 (2)H22A—C22—H22C109.5
O2—C9—C10126.6 (2)H22B—C22—H22C109.5
C2—N1—N2—C10.4 (3)C6—C5—C10—C91.0 (4)
C3—N4—N5—C4179.8 (2)C4—C5—C10—C9177.9 (2)
C12—N7—N8—C130.3 (3)N8—N7—C12—N60.3 (3)
C14—N9—N10—C15173.5 (3)C13—N6—C12—N70.1 (3)
N1—N2—C1—N30.0 (3)N7—N8—C13—N60.2 (3)
C2—N3—C1—N20.4 (3)N7—N8—C13—C14179.3 (3)
N2—N1—C2—N30.7 (3)C12—N6—C13—N80.0 (3)
N2—N1—C2—C3179.1 (2)C12—N6—C13—C14179.5 (3)
C1—N3—C2—N10.7 (3)N10—N9—C14—O45.6 (4)
C1—N3—C2—C3179.1 (3)N10—N9—C14—C13172.5 (2)
N5—N4—C3—O13.4 (4)N8—C13—C14—O4178.8 (3)
N5—N4—C3—C2177.7 (2)N6—C13—C14—O40.6 (4)
N1—C2—C3—O15.6 (4)N8—C13—C14—N90.7 (4)
N3—C2—C3—O1172.6 (3)N6—C13—C14—N9178.8 (2)
N1—C2—C3—N4173.3 (2)N9—N10—C15—C16177.1 (3)
N3—C2—C3—N48.5 (4)N10—C15—C16—C17170.1 (3)
N4—N5—C4—C5177.7 (2)N10—C15—C16—C218.9 (5)
N5—C4—C5—C6177.9 (3)C21—C16—C17—C181.3 (5)
N5—C4—C5—C103.2 (4)C15—C16—C17—C18177.6 (3)
C10—C5—C6—C70.5 (4)C16—C17—C18—C190.8 (5)
C4—C5—C6—C7178.5 (3)C17—C18—C19—O6180.0 (3)
C5—C6—C7—C80.2 (4)C17—C18—C19—C201.1 (5)
C6—C7—C8—O3179.1 (3)C22—O5—C20—C216.7 (4)
C6—C7—C8—C90.4 (4)C22—O5—C20—C19174.9 (3)
C11—O2—C9—C1011.8 (4)O6—C19—C20—O50.1 (4)
C11—O2—C9—C8168.4 (3)C18—C19—C20—O5179.0 (3)
O3—C8—C9—O20.5 (4)O6—C19—C20—C21178.5 (3)
C7—C8—C9—O2180.0 (2)C18—C19—C20—C212.6 (5)
O3—C8—C9—C10179.6 (3)O5—C20—C21—C16179.6 (3)
C7—C8—C9—C100.1 (4)C19—C20—C21—C162.1 (5)
O2—C9—C10—C5179.4 (3)C17—C16—C21—C200.2 (5)
C8—C9—C10—C50.8 (4)C15—C16—C21—C20179.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.822.182.642 (2)116
O3—H3···N80.822.252.868 (3)133
O6—H6A···N3i0.822.002.742 (3)149
O6—H6A···O50.822.222.665 (3)115
N2—H2···N6ii0.861.972.823 (3)172
N2—H2···O4ii0.862.563.016 (3)115
N4—H4···O6i0.862.253.089 (3)166
N7—H7···O1iii0.861.962.815 (3)174
N9—H9···O30.862.082.932 (3)170
Symmetry codes: (i) x, y+2, z+1; (ii) x3, y+1, z; (iii) x1, y+2, z.
 

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