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The title compound, C11H13N3O2, includes a planar phenylhydrazone moiety and a five-membered carbon ring in an envelope conformation. A short C-C bond distance of 1.435 (6) Å is observed in the five-membered ring. This may be due to the larger displacement parameters of relevant atoms. Neighboring molecules are linked to each other via hydrogen bonding, forming a zigzag supramolecular chain along the b axis.
Supporting information
CCDC reference: 200758
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.197
- Data-to-parameter ratio = 15.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(9) - C(10) = 1.43 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994).
Crystal data top
C11H13N3O2 | F(000) = 928 |
Mr = 219.24 | Dx = 1.285 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 21.372 (3) Å | θ = 4.4–12.1° |
b = 14.705 (4) Å | µ = 0.09 mm−1 |
c = 7.211 (2) Å | T = 298 K |
V = 2266.2 (9) Å3 | Prism, orange |
Z = 8 | 0.58 × 0.46 × 0.28 mm |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.057 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.4° |
Graphite monochromator | h = −10→26 |
ω/2θ scans | k = −7→18 |
2360 measured reflections | l = −8→3 |
2224 independent reflections | 3 standard reflections every 150 reflections |
789 reflections with I > 2σ(I) | intensity decay: 0.2% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0862P)2 + 0.1882P] where P = (Fo2 + 2Fc2)/3 |
2224 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−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 | x | y | z | Uiso*/Ueq | |
O1 | 0.31816 (12) | 0.29629 (18) | 0.8614 (6) | 0.1294 (13) | |
O2 | 0.37818 (13) | 0.18363 (19) | 0.9198 (6) | 0.1315 (13) | |
N1 | 0.32661 (15) | 0.2152 (2) | 0.8849 (6) | 0.0930 (11) | |
N2 | 0.12358 (11) | −0.01858 (17) | 0.8275 (4) | 0.0709 (9) | |
H2A | 0.1289 | −0.0755 | 0.8500 | 0.085* | |
N3 | 0.06469 (12) | 0.01408 (17) | 0.7798 (4) | 0.0681 (8) | |
C1 | 0.17287 (14) | 0.0401 (2) | 0.8386 (4) | 0.0593 (8) | |
C2 | 0.23131 (14) | 0.0074 (2) | 0.8927 (6) | 0.0720 (10) | |
H2 | 0.2363 | −0.0540 | 0.9202 | 0.086* | |
C3 | 0.28102 (15) | 0.0645 (2) | 0.9057 (5) | 0.0737 (10) | |
H3 | 0.3199 | 0.0420 | 0.9416 | 0.088* | |
C4 | 0.27422 (14) | 0.1548 (2) | 0.8663 (5) | 0.0687 (10) | |
C5 | 0.21710 (16) | 0.1886 (2) | 0.8088 (6) | 0.0795 (11) | |
H5 | 0.2128 | 0.2499 | 0.7797 | 0.095* | |
C6 | 0.16698 (14) | 0.1313 (2) | 0.7950 (5) | 0.0733 (10) | |
H6 | 0.1285 | 0.1539 | 0.7559 | 0.088* | |
C7 | 0.02092 (16) | −0.0454 (2) | 0.7755 (5) | 0.0694 (9) | |
C8 | 0.02464 (16) | −0.1444 (2) | 0.8125 (6) | 0.0927 (12) | |
H8A | 0.0400 | −0.1560 | 0.9370 | 0.111* | |
H8B | 0.0521 | −0.1742 | 0.7242 | 0.111* | |
C9 | −0.0420 (2) | −0.1775 (3) | 0.7909 (9) | 0.143 (2) | |
H9A | −0.0429 | −0.2337 | 0.7205 | 0.172* | |
H9B | −0.0605 | −0.1886 | 0.9116 | 0.172* | |
C10 | −0.0762 (2) | −0.1079 (4) | 0.6950 (8) | 0.135 (2) | |
H10A | −0.1188 | −0.1053 | 0.7417 | 0.162* | |
H10B | −0.0779 | −0.1218 | 0.5636 | 0.162* | |
C11 | −0.04477 (15) | −0.0184 (3) | 0.7238 (5) | 0.0834 (11) | |
H11A | −0.0646 | 0.0157 | 0.8229 | 0.100* | |
H11B | −0.0453 | 0.0177 | 0.6113 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0873 (19) | 0.0593 (17) | 0.242 (4) | −0.0127 (14) | 0.008 (2) | 0.004 (2) |
O2 | 0.0691 (18) | 0.094 (2) | 0.232 (4) | −0.0164 (16) | −0.027 (2) | 0.020 (2) |
N1 | 0.064 (2) | 0.0660 (19) | 0.149 (3) | −0.0058 (16) | 0.007 (2) | 0.004 (2) |
N2 | 0.0501 (15) | 0.0577 (15) | 0.105 (2) | 0.0016 (12) | −0.0048 (15) | 0.0002 (16) |
N3 | 0.0511 (16) | 0.0747 (18) | 0.079 (2) | 0.0031 (14) | 0.0001 (13) | 0.0013 (15) |
C1 | 0.0522 (18) | 0.0565 (17) | 0.069 (2) | 0.0015 (15) | 0.0055 (16) | −0.0039 (16) |
C2 | 0.058 (2) | 0.0509 (16) | 0.107 (3) | 0.0037 (17) | −0.0096 (19) | 0.0077 (19) |
C3 | 0.0586 (19) | 0.060 (2) | 0.102 (3) | 0.0047 (15) | −0.0109 (19) | 0.005 (2) |
C4 | 0.0546 (18) | 0.0589 (19) | 0.093 (3) | −0.0048 (16) | 0.0050 (18) | −0.0001 (19) |
C5 | 0.065 (2) | 0.0499 (19) | 0.123 (3) | 0.0060 (16) | 0.007 (2) | 0.010 (2) |
C6 | 0.0520 (18) | 0.063 (2) | 0.105 (3) | 0.0063 (16) | 0.0002 (18) | 0.0078 (18) |
C7 | 0.057 (2) | 0.083 (2) | 0.068 (2) | −0.0023 (18) | 0.0031 (17) | −0.001 (2) |
C8 | 0.068 (2) | 0.081 (2) | 0.129 (4) | −0.0132 (19) | −0.004 (2) | −0.008 (2) |
C9 | 0.094 (3) | 0.111 (4) | 0.224 (6) | −0.031 (3) | −0.031 (4) | 0.010 (4) |
C10 | 0.088 (3) | 0.143 (4) | 0.175 (6) | −0.036 (3) | −0.039 (3) | 0.017 (4) |
C11 | 0.0522 (19) | 0.116 (3) | 0.082 (3) | 0.000 (2) | −0.0021 (18) | 0.002 (2) |
Geometric parameters (Å, º) top
O1—N1 | 1.218 (4) | C5—H5 | 0.9300 |
O2—N1 | 1.222 (4) | C6—H6 | 0.9300 |
N1—C4 | 1.436 (4) | C7—C8 | 1.483 (5) |
N2—C1 | 1.364 (4) | C7—C11 | 1.505 (5) |
N2—N3 | 1.390 (3) | C8—C9 | 1.513 (5) |
N2—H2A | 0.8600 | C8—H8A | 0.9700 |
N3—C7 | 1.280 (4) | C8—H8B | 0.9700 |
C1—C6 | 1.384 (4) | C9—C10 | 1.435 (6) |
C1—C2 | 1.394 (4) | C9—H9A | 0.9700 |
C2—C3 | 1.357 (4) | C9—H9B | 0.9700 |
C2—H2 | 0.9300 | C10—C11 | 1.492 (6) |
C3—C4 | 1.365 (4) | C10—H10A | 0.9700 |
C3—H3 | 0.9300 | C10—H10B | 0.9700 |
C4—C5 | 1.382 (4) | C11—H11A | 0.9700 |
C5—C6 | 1.366 (4) | C11—H11B | 0.9700 |
| | | |
O1—N1—O2 | 122.3 (3) | N3—C7—C11 | 120.5 (3) |
O1—N1—C4 | 118.5 (3) | C8—C7—C11 | 110.7 (3) |
O2—N1—C4 | 119.2 (3) | C7—C8—C9 | 104.3 (3) |
C1—N2—N3 | 119.7 (2) | C7—C8—H8A | 110.9 |
C1—N2—H2A | 120.2 | C9—C8—H8A | 110.9 |
N3—N2—H2A | 120.2 | C7—C8—H8B | 110.9 |
C7—N3—N2 | 115.6 (3) | C9—C8—H8B | 110.9 |
N2—C1—C6 | 122.0 (3) | H8A—C8—H8B | 108.9 |
N2—C1—C2 | 119.3 (3) | C10—C9—C8 | 107.5 (4) |
C6—C1—C2 | 118.7 (3) | C10—C9—H9A | 110.2 |
C3—C2—C1 | 120.5 (3) | C8—C9—H9A | 110.2 |
C3—C2—H2 | 119.8 | C10—C9—H9B | 110.2 |
C1—C2—H2 | 119.8 | C8—C9—H9B | 110.2 |
C2—C3—C4 | 120.2 (3) | H9A—C9—H9B | 108.5 |
C2—C3—H3 | 119.9 | C9—C10—C11 | 109.4 (4) |
C4—C3—H3 | 119.9 | C9—C10—H10A | 109.8 |
C3—C4—C5 | 120.4 (3) | C11—C10—H10A | 109.8 |
C3—C4—N1 | 119.9 (3) | C9—C10—H10B | 109.8 |
C5—C4—N1 | 119.6 (3) | C11—C10—H10B | 109.8 |
C6—C5—C4 | 119.5 (3) | H10A—C10—H10B | 108.3 |
C6—C5—H5 | 120.2 | C10—C11—C7 | 102.9 (3) |
C4—C5—H5 | 120.2 | C10—C11—H11A | 111.2 |
C5—C6—C1 | 120.6 (3) | C7—C11—H11A | 111.2 |
C5—C6—H6 | 119.7 | C10—C11—H11B | 111.2 |
C1—C6—H6 | 119.7 | C7—C11—H11B | 111.2 |
N3—C7—C8 | 128.8 (3) | H11A—C11—H11B | 109.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 2.20 | 3.004 (4) | 155 |
C2—H2···O1i | 0.93 | 2.53 | 3.287 (4) | 139 |
Symmetry code: (i) −x+1/2, y−1/2, z. |
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