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The mol­ecule of the title Schiff base compound, C16H20N2O2, lies on a crystallographic twofold rotation axis. The crystal structure is stabilized by weaker inter­molecular C—H...O and stronger intra­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013384/rk2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013384/rk2007Isup2.hkl
Contains datablock I

CCDC reference: 647307

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.101
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H7 .. O1 .. 3.08 Ang.
Alert level C PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. O1 .. 3.98 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4,4'-(p-Phenylenediimino)dipent-3-en-2-one top
Crystal data top
C16H20N2O2F(000) = 584
Mr = 272.34Dx = 1.279 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 9247 reflections
a = 10.675 (2) Åθ = 6.0–54.8°
b = 8.8373 (18) ŵ = 0.09 mm1
c = 14.995 (3) ÅT = 295 K
V = 1414.5 (5) Å3Block, colorless
Z = 40.1 × 0.1 × 0.1 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1343 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 27.4°, θmin = 3.0°
φ and ω scansh = 1313
12933 measured reflectionsk = 1111
1610 independent reflectionsl = 1719
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.6162P]
where P = (Fo2 + 2Fc2)/3
1610 reflections(Δ/σ)max < 0.001
97 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.53222 (9)0.34729 (11)0.41410 (6)0.0227 (2)
N10.56091 (10)0.19379 (11)0.56670 (7)0.0157 (2)
C10.67529 (12)0.30665 (15)0.29393 (8)0.0218 (3)
H5A0.60740.33310.25490.033*
H5B0.71720.21860.27120.033*
H5C0.73340.38930.29720.033*
C20.62440 (11)0.27335 (14)0.38626 (8)0.0167 (3)
C30.68631 (12)0.15931 (14)0.43742 (8)0.0174 (3)
H30.75160.10670.41050.021*
C40.65573 (11)0.12185 (13)0.52417 (8)0.0154 (3)
C50.73048 (12)0.00274 (15)0.57165 (8)0.0221 (3)
H1A0.74480.03370.63220.033*
H1B0.80940.01070.54200.033*
H1C0.68510.09100.57120.033*
C60.53065 (11)0.18780 (13)0.65904 (8)0.0144 (3)
C70.51441 (11)0.05151 (13)0.70470 (8)0.0153 (3)
H70.52290.03980.67450.018*
C80.51516 (11)0.32417 (13)0.70475 (8)0.0156 (3)
H80.52510.41550.67470.019*
H10.5266 (16)0.271 (2)0.5333 (11)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0223 (5)0.0264 (5)0.0195 (5)0.0070 (4)0.0044 (4)0.0050 (4)
N10.0175 (5)0.0168 (5)0.0129 (5)0.0026 (4)0.0006 (4)0.0011 (4)
C10.0214 (6)0.0269 (7)0.0172 (6)0.0013 (5)0.0025 (5)0.0018 (5)
C20.0166 (6)0.0192 (6)0.0144 (5)0.0035 (5)0.0002 (4)0.0017 (4)
C30.0178 (6)0.0193 (6)0.0151 (6)0.0013 (5)0.0009 (4)0.0037 (4)
C40.0158 (6)0.0149 (6)0.0156 (6)0.0004 (4)0.0021 (4)0.0032 (4)
C50.0237 (7)0.0254 (6)0.0173 (6)0.0091 (5)0.0004 (5)0.0006 (5)
C60.0123 (6)0.0177 (6)0.0133 (6)0.0001 (4)0.0008 (4)0.0005 (4)
C70.0158 (6)0.0135 (5)0.0165 (6)0.0003 (4)0.0010 (4)0.0017 (4)
C80.0150 (6)0.0139 (6)0.0178 (6)0.0001 (4)0.0013 (4)0.0027 (4)
Geometric parameters (Å, º) top
O1—C21.2528 (15)C4—C51.5005 (16)
N1—C41.3548 (15)C5—H1A0.9600
N1—C61.4227 (15)C5—H1B0.9600
N1—H10.920 (18)C5—H1C0.9600
C1—C21.5161 (17)C6—C71.3962 (16)
C1—H5A0.9600C6—C81.3963 (16)
C1—H5B0.9600C7—C7i1.393 (2)
C1—H5C0.9600C7—H70.9300
C2—C31.4285 (17)C8—C8i1.395 (2)
C3—C41.3813 (17)C8—H80.9300
C3—H30.9300
C4—N1—C6127.61 (10)C3—C4—C5119.30 (11)
C4—N1—H1112.8 (11)C4—C5—H1A109.5
C6—N1—H1117.8 (11)C4—C5—H1B109.5
C2—C1—H5A109.5H1A—C5—H1B109.5
C2—C1—H5B109.5C4—C5—H1C109.5
H5A—C1—H5B109.5H1A—C5—H1C109.5
C2—C1—H5C109.5H1B—C5—H1C109.5
H5A—C1—H5C109.5C7—C6—C8119.28 (11)
H5B—C1—H5C109.5C7—C6—N1122.52 (10)
O1—C2—C3123.53 (11)C8—C6—N1118.20 (10)
O1—C2—C1118.98 (11)C7i—C7—C6120.38 (7)
C3—C2—C1117.49 (11)C7i—C7—H7119.8
C4—C3—C2124.43 (11)C6—C7—H7119.8
C4—C3—H3117.8C8i—C8—C6120.33 (7)
C2—C3—H3117.8C8i—C8—H8119.8
N1—C4—C3120.49 (11)C6—C8—H8119.8
N1—C4—C5120.20 (11)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1ii0.933.083.9803 (16)163
N1—H1···O10.920 (18)1.913 (17)2.6776 (14)139.3 (15)
Symmetry code: (ii) x+1, y, z+1.
 

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