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In the crystal structure of the title compound, C15H12N4O·C2H6O, mol­ecules are linked via weak inter­molecular N—H...N, O—H...O and N—H...O hydrogen bonds, forming a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008361/is2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008361/is2009Isup2.hkl
Contains datablock I

CCDC reference: 605097

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.101
  • Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.752 0.983 Tmin(prime) and Tmax expected: 0.967 0.983 RR(prime) = 0.778 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.54
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 25.03 From the CIF: _reflns_number_total 1651 Count of symmetry unique reflns 1651 Completeness (_total/calc) 100.00% 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 3 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2'-(1H-Indol-3-ylmethylene)isonicotinohydrazide ethanol solvate top
Crystal data top
C15H12N4O·C2H6OF(000) = 656
Mr = 310.35Dx = 1.277 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4354 reflections
a = 9.6080 (14) Åθ = 2.4–24.6°
b = 10.0047 (15) ŵ = 0.09 mm1
c = 16.791 (3) ÅT = 294 K
V = 1614.1 (4) Å3Block, red
Z = 40.38 × 0.22 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1651 independent reflections
Radiation source: fine-focus sealed tube1554 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.752, Tmax = 0.983k = 119
8779 measured reflectionsl = 1918
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0653P)2 + 0.3045P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
1651 reflectionsΔρmax = 0.33 e Å3
219 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (3)
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
O10.08941 (18)0.16799 (16)0.13853 (11)0.0471 (5)
N10.5299 (2)0.3729 (2)0.24414 (15)0.0522 (6)
N20.2019 (2)0.00717 (18)0.19598 (12)0.0352 (4)
H2B0.287 (3)0.032 (3)0.2147 (15)0.047 (7)*
N30.10661 (19)0.10122 (17)0.16851 (11)0.0335 (4)
N40.0072 (2)0.5518 (2)0.14744 (13)0.0417 (5)
H4A0.020 (4)0.629 (3)0.1495 (19)0.062 (10)*
C10.3663 (2)0.2001 (2)0.27700 (14)0.0398 (5)
H10.33340.13930.31450.048*
C20.4767 (3)0.2844 (3)0.29491 (17)0.0493 (6)
H20.51580.27880.34550.059*
C30.4699 (3)0.3799 (3)0.17243 (18)0.0511 (6)
H30.50590.44050.13580.061*
C40.3578 (2)0.3028 (2)0.14937 (15)0.0433 (6)
H40.31760.31390.09940.052*
C50.3062 (2)0.2083 (2)0.20215 (14)0.0355 (5)
C60.1882 (2)0.1210 (2)0.17643 (13)0.0338 (5)
C70.1367 (2)0.2209 (2)0.18889 (13)0.0347 (5)
H70.21200.23420.22280.042*
C80.0603 (2)0.3358 (2)0.16203 (13)0.0339 (5)
C90.0564 (2)0.3460 (2)0.10809 (13)0.0330 (5)
C100.1345 (3)0.2543 (3)0.06413 (14)0.0428 (6)
H100.11460.16340.06610.051*
C110.2420 (3)0.3021 (3)0.01776 (16)0.0534 (7)
H110.29510.24220.01170.064*
C120.2729 (3)0.4392 (3)0.01404 (16)0.0547 (7)
H120.34730.46810.01690.066*
C130.1958 (3)0.5306 (3)0.05500 (15)0.0488 (7)
H130.21550.62150.05200.059*
C140.0871 (2)0.4832 (2)0.10130 (13)0.0364 (5)
C150.0940 (3)0.4646 (2)0.18306 (14)0.0390 (5)
H150.16640.48820.21700.047*
O20.8519 (3)0.8943 (3)0.05187 (17)0.0911 (9)
H2A0.92280.87610.07680.137*
C160.7366 (4)0.9142 (4)0.1075 (2)0.0801 (11)
H16A0.75150.99370.13940.096*
H16B0.72750.83790.14280.096*
C170.6110 (4)0.9289 (5)0.0578 (3)0.0904 (12)
H17A0.62780.99450.01720.136*
H17B0.53440.95700.09040.136*
H17C0.58920.84470.03330.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0406 (9)0.0296 (8)0.0711 (11)0.0013 (7)0.0185 (9)0.0017 (8)
N10.0382 (12)0.0431 (12)0.0753 (14)0.0081 (10)0.0075 (12)0.0037 (11)
N20.0301 (10)0.0269 (10)0.0485 (11)0.0011 (8)0.0066 (8)0.0008 (8)
N30.0304 (9)0.0281 (9)0.0420 (9)0.0018 (8)0.0022 (8)0.0016 (8)
N40.0508 (12)0.0228 (10)0.0516 (11)0.0009 (9)0.0005 (10)0.0011 (9)
C10.0343 (11)0.0367 (12)0.0484 (13)0.0025 (10)0.0011 (10)0.0011 (10)
C20.0422 (13)0.0474 (14)0.0583 (14)0.0056 (13)0.0110 (12)0.0052 (13)
C30.0430 (13)0.0390 (13)0.0714 (17)0.0101 (12)0.0004 (14)0.0070 (13)
C40.0390 (12)0.0369 (12)0.0541 (13)0.0039 (11)0.0035 (11)0.0049 (11)
C50.0287 (10)0.0274 (11)0.0503 (12)0.0034 (10)0.0013 (10)0.0030 (10)
C60.0313 (10)0.0289 (11)0.0413 (11)0.0013 (9)0.0024 (10)0.0007 (9)
C70.0326 (11)0.0305 (11)0.0412 (11)0.0006 (9)0.0029 (9)0.0004 (10)
C80.0327 (11)0.0297 (11)0.0394 (11)0.0008 (9)0.0005 (9)0.0007 (9)
C90.0333 (11)0.0289 (11)0.0368 (10)0.0011 (9)0.0023 (9)0.0009 (9)
C100.0479 (13)0.0345 (12)0.0460 (12)0.0028 (11)0.0046 (12)0.0011 (10)
C110.0524 (15)0.0558 (16)0.0520 (14)0.0059 (14)0.0165 (13)0.0016 (13)
C120.0495 (15)0.0619 (17)0.0526 (14)0.0089 (14)0.0112 (13)0.0070 (14)
C130.0576 (16)0.0404 (14)0.0485 (13)0.0146 (13)0.0003 (12)0.0068 (11)
C140.0408 (12)0.0296 (11)0.0387 (11)0.0034 (10)0.0039 (10)0.0004 (9)
C150.0394 (12)0.0308 (11)0.0470 (12)0.0024 (10)0.0049 (11)0.0024 (10)
O20.0644 (15)0.105 (2)0.1043 (19)0.0154 (15)0.0228 (15)0.0125 (17)
C160.092 (2)0.073 (2)0.075 (2)0.021 (2)0.024 (2)0.0129 (19)
C170.068 (2)0.097 (3)0.106 (3)0.008 (2)0.013 (2)0.013 (2)
Geometric parameters (Å, º) top
O1—C61.236 (3)C8—C151.374 (3)
N1—C21.331 (4)C8—C91.445 (3)
N1—C31.337 (4)C9—C101.396 (3)
N2—C61.330 (3)C9—C141.409 (3)
N2—N31.392 (3)C10—C111.378 (4)
N2—H2B0.91 (3)C10—H100.9300
N3—C71.278 (3)C11—C121.405 (4)
N4—C151.347 (3)C11—H110.9300
N4—C141.375 (3)C12—C131.363 (4)
N4—H4A0.78 (3)C12—H120.9300
C1—C51.385 (3)C13—C141.386 (3)
C1—C21.388 (4)C13—H130.9300
C1—H10.9300C15—H150.9300
C2—H20.9300O2—C161.462 (5)
C3—C41.381 (4)O2—H2A0.8200
C3—H30.9300C16—C171.474 (5)
C4—C51.387 (3)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C61.495 (3)C17—H17A0.9600
C7—C81.437 (3)C17—H17B0.9600
C7—H70.9300C17—H17C0.9600
C2—N1—C3116.5 (2)C10—C9—C8134.6 (2)
C6—N2—N3120.33 (19)C14—C9—C8106.37 (19)
C6—N2—H2B116.1 (17)C11—C10—C9118.3 (2)
N3—N2—H2B121.2 (18)C11—C10—H10120.9
C7—N3—N2113.29 (18)C9—C10—H10120.9
C7—C8—C9130.5 (2)C10—C11—C12121.5 (3)
C15—N4—C14109.56 (19)C10—C11—H11119.3
C15—C8—C7123.3 (2)C12—C11—H11119.3
C15—N4—H4A122 (3)C13—C12—C11121.2 (3)
C14—N4—H4A128 (3)C13—C12—H12119.4
C5—C1—C2118.6 (2)C11—C12—H12119.4
C5—C1—H1120.7C12—C13—C14117.6 (2)
C2—C1—H1120.7C12—C13—H13121.2
N1—C2—C1124.0 (3)C14—C13—H13121.2
N1—C2—H2118.0N4—C14—C13129.9 (2)
C1—C2—H2118.0N4—C14—C9107.62 (19)
N1—C3—C4124.0 (2)C13—C14—C9122.5 (2)
N1—C3—H3118.0N4—C15—C8110.3 (2)
C4—C3—H3118.0N4—C15—H15124.8
C3—C4—C5118.7 (2)C8—C15—H15124.8
C3—C4—H4120.6C16—O2—H2A109.5
C5—C4—H4120.6O2—C16—C17105.8 (3)
C1—C5—C4118.1 (2)O2—C16—H16A110.6
C1—C5—C6122.9 (2)C17—C16—H16A110.6
C4—C5—C6119.0 (2)O2—C16—H16B110.6
O1—C6—N2124.7 (2)C17—C16—H16B110.6
O1—C6—C5120.6 (2)H16A—C16—H16B108.7
N2—C6—C5114.64 (19)C16—C17—H17A109.5
N3—C7—C8123.3 (2)C16—C17—H17B109.5
N3—C7—H7118.3H17A—C17—H17B109.5
C8—C7—H7118.3C16—C17—H17C109.5
C15—C8—C9106.1 (2)H17A—C17—H17C109.5
C10—C9—C14119.0 (2)H17B—C17—H17C109.5
C6—N2—N3—C7176.8 (2)C7—C8—C9—C100.1 (4)
C3—N1—C2—C11.0 (4)C15—C8—C9—C141.0 (3)
C5—C1—C2—N10.6 (4)C7—C8—C9—C14178.3 (2)
C2—N1—C3—C40.5 (4)C14—C9—C10—C112.1 (4)
N1—C3—C4—C52.5 (4)C8—C9—C10—C11179.9 (3)
C2—C1—C5—C41.4 (3)C9—C10—C11—C120.2 (4)
C2—C1—C5—C6179.2 (2)C10—C11—C12—C131.4 (5)
C3—C4—C5—C12.8 (3)C11—C12—C13—C140.9 (4)
C3—C4—C5—C6177.8 (2)C15—N4—C14—C13179.2 (2)
N3—N2—C6—O15.0 (4)C15—N4—C14—C90.5 (3)
N3—N2—C6—C5173.37 (18)C12—C13—C14—N4179.2 (2)
C1—C5—C6—O1137.5 (2)C12—C13—C14—C91.1 (4)
C4—C5—C6—O141.9 (3)C10—C9—C14—N4177.6 (2)
C1—C5—C6—N244.0 (3)C8—C9—C14—N40.9 (3)
C4—C5—C6—N2136.6 (2)C10—C9—C14—C132.7 (4)
N2—N3—C7—C8174.7 (2)C8—C9—C14—C13178.8 (2)
N3—C7—C8—C15179.0 (2)C14—N4—C15—C80.1 (3)
N3—C7—C8—C92.2 (4)C7—C8—C15—N4178.2 (2)
C15—C8—C9—C10177.2 (3)C9—C8—C15—N40.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N1i0.91 (3)2.12 (3)3.015 (3)169 (2)
N4—H4A···O1ii0.78 (3)2.15 (3)2.917 (3)168 (3)
O2—H2A···O1iii0.821.962.778 (3)179
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y+1, z.
 

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