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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201841X/cv6152sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201841X/cv6152Isup2.hkl
Contains datablock I

CCDC reference: 200758

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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).

(I) top
Crystal data top
C11H13N3O2F(000) = 928
Mr = 219.24Dx = 1.285 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 21.372 (3) Åθ = 4.4–12.1°
b = 14.705 (4) ŵ = 0.09 mm1
c = 7.211 (2) ÅT = 298 K
V = 2266.2 (9) Å3Prism, orange
Z = 80.58 × 0.46 × 0.28 mm
Data collection top
Rigaku AFC-7S
diffractometer
Rint = 0.057
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.4°
Graphite monochromatorh = 1026
ω/2θ scansk = 718
2360 measured reflectionsl = 83
2224 independent reflections3 standard reflections every 150 reflections
789 reflections with I > 2σ(I) intensity decay: 0.2%
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-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 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.14 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
O10.31816 (12)0.29629 (18)0.8614 (6)0.1294 (13)
O20.37818 (13)0.18363 (19)0.9198 (6)0.1315 (13)
N10.32661 (15)0.2152 (2)0.8849 (6)0.0930 (11)
N20.12358 (11)0.01858 (17)0.8275 (4)0.0709 (9)
H2A0.12890.07550.85000.085*
N30.06469 (12)0.01408 (17)0.7798 (4)0.0681 (8)
C10.17287 (14)0.0401 (2)0.8386 (4)0.0593 (8)
C20.23131 (14)0.0074 (2)0.8927 (6)0.0720 (10)
H20.23630.05400.92020.086*
C30.28102 (15)0.0645 (2)0.9057 (5)0.0737 (10)
H30.31990.04200.94160.088*
C40.27422 (14)0.1548 (2)0.8663 (5)0.0687 (10)
C50.21710 (16)0.1886 (2)0.8088 (6)0.0795 (11)
H50.21280.24990.77970.095*
C60.16698 (14)0.1313 (2)0.7950 (5)0.0733 (10)
H60.12850.15390.75590.088*
C70.02092 (16)0.0454 (2)0.7755 (5)0.0694 (9)
C80.02464 (16)0.1444 (2)0.8125 (6)0.0927 (12)
H8A0.04000.15600.93700.111*
H8B0.05210.17420.72420.111*
C90.0420 (2)0.1775 (3)0.7909 (9)0.143 (2)
H9A0.04290.23370.72050.172*
H9B0.06050.18860.91160.172*
C100.0762 (2)0.1079 (4)0.6950 (8)0.135 (2)
H10A0.11880.10530.74170.162*
H10B0.07790.12180.56360.162*
C110.04477 (15)0.0184 (3)0.7238 (5)0.0834 (11)
H11A0.06460.01570.82290.100*
H11B0.04530.01770.61130.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0873 (19)0.0593 (17)0.242 (4)0.0127 (14)0.008 (2)0.004 (2)
O20.0691 (18)0.094 (2)0.232 (4)0.0164 (16)0.027 (2)0.020 (2)
N10.064 (2)0.0660 (19)0.149 (3)0.0058 (16)0.007 (2)0.004 (2)
N20.0501 (15)0.0577 (15)0.105 (2)0.0016 (12)0.0048 (15)0.0002 (16)
N30.0511 (16)0.0747 (18)0.079 (2)0.0031 (14)0.0001 (13)0.0013 (15)
C10.0522 (18)0.0565 (17)0.069 (2)0.0015 (15)0.0055 (16)0.0039 (16)
C20.058 (2)0.0509 (16)0.107 (3)0.0037 (17)0.0096 (19)0.0077 (19)
C30.0586 (19)0.060 (2)0.102 (3)0.0047 (15)0.0109 (19)0.005 (2)
C40.0546 (18)0.0589 (19)0.093 (3)0.0048 (16)0.0050 (18)0.0001 (19)
C50.065 (2)0.0499 (19)0.123 (3)0.0060 (16)0.007 (2)0.010 (2)
C60.0520 (18)0.063 (2)0.105 (3)0.0063 (16)0.0002 (18)0.0078 (18)
C70.057 (2)0.083 (2)0.068 (2)0.0023 (18)0.0031 (17)0.001 (2)
C80.068 (2)0.081 (2)0.129 (4)0.0132 (19)0.004 (2)0.008 (2)
C90.094 (3)0.111 (4)0.224 (6)0.031 (3)0.031 (4)0.010 (4)
C100.088 (3)0.143 (4)0.175 (6)0.036 (3)0.039 (3)0.017 (4)
C110.0522 (19)0.116 (3)0.082 (3)0.000 (2)0.0021 (18)0.002 (2)
Geometric parameters (Å, º) top
O1—N11.218 (4)C5—H50.9300
O2—N11.222 (4)C6—H60.9300
N1—C41.436 (4)C7—C81.483 (5)
N2—C11.364 (4)C7—C111.505 (5)
N2—N31.390 (3)C8—C91.513 (5)
N2—H2A0.8600C8—H8A0.9700
N3—C71.280 (4)C8—H8B0.9700
C1—C61.384 (4)C9—C101.435 (6)
C1—C21.394 (4)C9—H9A0.9700
C2—C31.357 (4)C9—H9B0.9700
C2—H20.9300C10—C111.492 (6)
C3—C41.365 (4)C10—H10A0.9700
C3—H30.9300C10—H10B0.9700
C4—C51.382 (4)C11—H11A0.9700
C5—C61.366 (4)C11—H11B0.9700
O1—N1—O2122.3 (3)N3—C7—C11120.5 (3)
O1—N1—C4118.5 (3)C8—C7—C11110.7 (3)
O2—N1—C4119.2 (3)C7—C8—C9104.3 (3)
C1—N2—N3119.7 (2)C7—C8—H8A110.9
C1—N2—H2A120.2C9—C8—H8A110.9
N3—N2—H2A120.2C7—C8—H8B110.9
C7—N3—N2115.6 (3)C9—C8—H8B110.9
N2—C1—C6122.0 (3)H8A—C8—H8B108.9
N2—C1—C2119.3 (3)C10—C9—C8107.5 (4)
C6—C1—C2118.7 (3)C10—C9—H9A110.2
C3—C2—C1120.5 (3)C8—C9—H9A110.2
C3—C2—H2119.8C10—C9—H9B110.2
C1—C2—H2119.8C8—C9—H9B110.2
C2—C3—C4120.2 (3)H9A—C9—H9B108.5
C2—C3—H3119.9C9—C10—C11109.4 (4)
C4—C3—H3119.9C9—C10—H10A109.8
C3—C4—C5120.4 (3)C11—C10—H10A109.8
C3—C4—N1119.9 (3)C9—C10—H10B109.8
C5—C4—N1119.6 (3)C11—C10—H10B109.8
C6—C5—C4119.5 (3)H10A—C10—H10B108.3
C6—C5—H5120.2C10—C11—C7102.9 (3)
C4—C5—H5120.2C10—C11—H11A111.2
C5—C6—C1120.6 (3)C7—C11—H11A111.2
C5—C6—H6119.7C10—C11—H11B111.2
C1—C6—H6119.7C7—C11—H11B111.2
N3—C7—C8128.8 (3)H11A—C11—H11B109.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.203.004 (4)155
C2—H2···O1i0.932.533.287 (4)139
Symmetry code: (i) x+1/2, y1/2, z.
 

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