The molecule of the title Schiff base compound, C
16H
20N
2O
2, 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
CCDC reference: 647307
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C16H20N2O2 | F(000) = 584 |
Mr = 272.34 | Dx = 1.279 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 9247 reflections |
a = 10.675 (2) Å | θ = 6.0–54.8° |
b = 8.8373 (18) Å | µ = 0.09 mm−1 |
c = 14.995 (3) Å | T = 295 K |
V = 1414.5 (5) Å3 | Block, colorless |
Z = 4 | 0.1 × 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 tube | Rint = 0.043 |
Graphite monochromator | θmax = 27.4°, θmin = 3.0° |
φ and ω scans | h = −13→13 |
12933 measured reflections | k = −11→11 |
1610 independent reflections | l = −17→19 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H 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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.53222 (9) | 0.34729 (11) | 0.41410 (6) | 0.0227 (2) | |
N1 | 0.56091 (10) | 0.19379 (11) | 0.56670 (7) | 0.0157 (2) | |
C1 | 0.67529 (12) | 0.30665 (15) | 0.29393 (8) | 0.0218 (3) | |
H5A | 0.6074 | 0.3331 | 0.2549 | 0.033* | |
H5B | 0.7172 | 0.2186 | 0.2712 | 0.033* | |
H5C | 0.7334 | 0.3893 | 0.2972 | 0.033* | |
C2 | 0.62440 (11) | 0.27335 (14) | 0.38626 (8) | 0.0167 (3) | |
C3 | 0.68631 (12) | 0.15931 (14) | 0.43742 (8) | 0.0174 (3) | |
H3 | 0.7516 | 0.1067 | 0.4105 | 0.021* | |
C4 | 0.65573 (11) | 0.12185 (13) | 0.52417 (8) | 0.0154 (3) | |
C5 | 0.73048 (12) | 0.00274 (15) | 0.57165 (8) | 0.0221 (3) | |
H1A | 0.7448 | 0.0337 | 0.6322 | 0.033* | |
H1B | 0.8094 | −0.0107 | 0.5420 | 0.033* | |
H1C | 0.6851 | −0.0910 | 0.5712 | 0.033* | |
C6 | 0.53065 (11) | 0.18780 (13) | 0.65904 (8) | 0.0144 (3) | |
C7 | 0.51441 (11) | 0.05151 (13) | 0.70470 (8) | 0.0153 (3) | |
H7 | 0.5229 | −0.0398 | 0.6745 | 0.018* | |
C8 | 0.51516 (11) | 0.32417 (13) | 0.70475 (8) | 0.0156 (3) | |
H8 | 0.5251 | 0.4155 | 0.6747 | 0.019* | |
H1 | 0.5266 (16) | 0.271 (2) | 0.5333 (11) | 0.032 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0223 (5) | 0.0264 (5) | 0.0195 (5) | 0.0070 (4) | 0.0044 (4) | 0.0050 (4) |
N1 | 0.0175 (5) | 0.0168 (5) | 0.0129 (5) | 0.0026 (4) | 0.0006 (4) | 0.0011 (4) |
C1 | 0.0214 (6) | 0.0269 (7) | 0.0172 (6) | −0.0013 (5) | 0.0025 (5) | 0.0018 (5) |
C2 | 0.0166 (6) | 0.0192 (6) | 0.0144 (5) | −0.0035 (5) | −0.0002 (4) | −0.0017 (4) |
C3 | 0.0178 (6) | 0.0193 (6) | 0.0151 (6) | 0.0013 (5) | 0.0009 (4) | −0.0037 (4) |
C4 | 0.0158 (6) | 0.0149 (6) | 0.0156 (6) | −0.0004 (4) | −0.0021 (4) | −0.0032 (4) |
C5 | 0.0237 (7) | 0.0254 (6) | 0.0173 (6) | 0.0091 (5) | 0.0004 (5) | 0.0006 (5) |
C6 | 0.0123 (6) | 0.0177 (6) | 0.0133 (6) | 0.0001 (4) | −0.0008 (4) | −0.0005 (4) |
C7 | 0.0158 (6) | 0.0135 (5) | 0.0165 (6) | −0.0003 (4) | −0.0010 (4) | −0.0017 (4) |
C8 | 0.0150 (6) | 0.0139 (6) | 0.0178 (6) | −0.0001 (4) | 0.0013 (4) | 0.0027 (4) |
Geometric parameters (Å, º) top
O1—C2 | 1.2528 (15) | C4—C5 | 1.5005 (16) |
N1—C4 | 1.3548 (15) | C5—H1A | 0.9600 |
N1—C6 | 1.4227 (15) | C5—H1B | 0.9600 |
N1—H1 | 0.920 (18) | C5—H1C | 0.9600 |
C1—C2 | 1.5161 (17) | C6—C7 | 1.3962 (16) |
C1—H5A | 0.9600 | C6—C8 | 1.3963 (16) |
C1—H5B | 0.9600 | C7—C7i | 1.393 (2) |
C1—H5C | 0.9600 | C7—H7 | 0.9300 |
C2—C3 | 1.4285 (17) | C8—C8i | 1.395 (2) |
C3—C4 | 1.3813 (17) | C8—H8 | 0.9300 |
C3—H3 | 0.9300 | | |
| | | |
C4—N1—C6 | 127.61 (10) | C3—C4—C5 | 119.30 (11) |
C4—N1—H1 | 112.8 (11) | C4—C5—H1A | 109.5 |
C6—N1—H1 | 117.8 (11) | C4—C5—H1B | 109.5 |
C2—C1—H5A | 109.5 | H1A—C5—H1B | 109.5 |
C2—C1—H5B | 109.5 | C4—C5—H1C | 109.5 |
H5A—C1—H5B | 109.5 | H1A—C5—H1C | 109.5 |
C2—C1—H5C | 109.5 | H1B—C5—H1C | 109.5 |
H5A—C1—H5C | 109.5 | C7—C6—C8 | 119.28 (11) |
H5B—C1—H5C | 109.5 | C7—C6—N1 | 122.52 (10) |
O1—C2—C3 | 123.53 (11) | C8—C6—N1 | 118.20 (10) |
O1—C2—C1 | 118.98 (11) | C7i—C7—C6 | 120.38 (7) |
C3—C2—C1 | 117.49 (11) | C7i—C7—H7 | 119.8 |
C4—C3—C2 | 124.43 (11) | C6—C7—H7 | 119.8 |
C4—C3—H3 | 117.8 | C8i—C8—C6 | 120.33 (7) |
C2—C3—H3 | 117.8 | C8i—C8—H8 | 119.8 |
N1—C4—C3 | 120.49 (11) | C6—C8—H8 | 119.8 |
N1—C4—C5 | 120.20 (11) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1ii | 0.93 | 3.08 | 3.9803 (16) | 163 |
N1—H1···O1 | 0.920 (18) | 1.913 (17) | 2.6776 (14) | 139.3 (15) |
Symmetry code: (ii) −x+1, −y, −z+1. |