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organic compounds
Excluding H atoms, the title molecule, C12H15O3N3, is approximately planar. Glide-related molecules are linked by intermolecular O—HO hydrogen bonds into a chain structure running along [101]. The crystal packing is further stabilized by π–π interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032672/ci6504sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032672/ci6504Isup2.hkl |
CCDC reference: 262468
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.133
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H13 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3-(Hydroxyimino)butan-2-one (4-methoxybenzoyl)hydrazone top
Crystal data top
C12H15N3O3 | F(000) = 528 |
Mr = 249.27 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 10756 reflections |
a = 6.8829 (14) Å | θ = 3.1–27.5° |
b = 23.589 (5) Å | µ = 0.10 mm−1 |
c = 7.7372 (15) Å | T = 296 K |
β = 95.66 (3)° | Prism, yellow |
V = 1250.1 (4) Å3 | 0.39 × 0.26 × 0.22 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2847 independent reflections |
Radiation source: fine-focus sealed tube | 2092 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −30→30 |
Tmin = 0.969, Tmax = 0.978 | l = −10→9 |
12054 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.0771P] where P = (Fo2 + 2Fc2)/3 |
2847 reflections | (Δ/σ)max = 0.001 |
169 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.59233 (15) | 0.79936 (5) | 0.33748 (15) | 0.0406 (3) | |
N2 | 0.71661 (15) | 0.67305 (4) | 0.54605 (15) | 0.0391 (3) | |
N3 | 0.62210 (16) | 0.62664 (5) | 0.60587 (16) | 0.0432 (3) | |
O1 | 0.69009 (14) | 0.84679 (4) | 0.28100 (15) | 0.0489 (3) | |
O2 | 0.90419 (13) | 0.57946 (4) | 0.68091 (15) | 0.0525 (3) | |
O3 | 0.33317 (17) | 0.38699 (4) | 0.87553 (17) | 0.0639 (4) | |
C1 | 0.92557 (19) | 0.76493 (6) | 0.4257 (2) | 0.0502 (4) | |
C2 | 0.70796 (17) | 0.76102 (5) | 0.40479 (17) | 0.0357 (3) | |
C3 | 0.60694 (17) | 0.71029 (5) | 0.46378 (17) | 0.0372 (3) | |
C4 | 0.3902 (2) | 0.70507 (7) | 0.4215 (2) | 0.0572 (4) | |
C5 | 0.72511 (18) | 0.58123 (5) | 0.67079 (18) | 0.0387 (3) | |
C6 | 0.60856 (19) | 0.53238 (5) | 0.72376 (17) | 0.0379 (3) | |
C7 | 0.40887 (19) | 0.52634 (6) | 0.68215 (18) | 0.0417 (3) | |
C8 | 0.3104 (2) | 0.47842 (6) | 0.72998 (19) | 0.0451 (3) | |
C9 | 0.4133 (2) | 0.43586 (6) | 0.82185 (19) | 0.0458 (3) | |
C10 | 0.6127 (2) | 0.44143 (6) | 0.8657 (2) | 0.0519 (4) | |
C11 | 0.7080 (2) | 0.48898 (6) | 0.8164 (2) | 0.0473 (4) | |
C12 | 0.1271 (3) | 0.38041 (8) | 0.8473 (3) | 0.0721 (6) | |
H1A | 0.9757 | 0.7548 | 0.3185 | 0.075* | |
H1B | 0.9769 | 0.7395 | 0.5158 | 0.075* | |
H1C | 0.9640 | 0.8030 | 0.4563 | 0.075* | |
H4A | 0.3610 | 0.6703 | 0.3598 | 0.086* | |
H4B | 0.3431 | 0.7365 | 0.3507 | 0.086* | |
H4C | 0.3278 | 0.7050 | 0.5272 | 0.086* | |
H7 | 0.3396 | 0.5550 | 0.6209 | 0.050* | |
H8 | 0.1767 | 0.4749 | 0.7006 | 0.054* | |
H10 | 0.6816 | 0.4130 | 0.9284 | 0.062* | |
H11 | 0.8419 | 0.4922 | 0.8455 | 0.057* | |
H12A | 0.0647 | 0.4098 | 0.9076 | 0.108* | |
H12B | 0.0909 | 0.3441 | 0.8900 | 0.108* | |
H12C | 0.0865 | 0.3829 | 0.7252 | 0.108* | |
H13 | 0.4968 | 0.6265 | 0.6020 | 0.052* | |
H14 | 0.596 (2) | 0.8670 (7) | 0.237 (2) | 0.073* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0378 (6) | 0.0383 (6) | 0.0461 (7) | 0.0051 (5) | 0.0060 (5) | 0.0049 (5) |
N2 | 0.0361 (5) | 0.0350 (6) | 0.0459 (7) | −0.0012 (4) | 0.0024 (5) | 0.0021 (5) |
N3 | 0.0349 (5) | 0.0379 (6) | 0.0566 (8) | −0.0019 (4) | 0.0031 (5) | 0.0075 (5) |
O1 | 0.0445 (5) | 0.0372 (5) | 0.0657 (7) | 0.0071 (4) | 0.0082 (5) | 0.0126 (5) |
O2 | 0.0374 (5) | 0.0374 (5) | 0.0811 (8) | −0.0017 (4) | −0.0026 (5) | 0.0002 (5) |
O3 | 0.0650 (7) | 0.0403 (6) | 0.0886 (9) | −0.0035 (5) | 0.0191 (6) | 0.0139 (6) |
C1 | 0.0340 (7) | 0.0485 (8) | 0.0672 (10) | 0.0008 (6) | 0.0009 (6) | 0.0159 (7) |
C2 | 0.0323 (6) | 0.0372 (7) | 0.0375 (7) | 0.0042 (5) | 0.0027 (5) | 0.0002 (5) |
C3 | 0.0327 (6) | 0.0397 (7) | 0.0392 (7) | 0.0024 (5) | 0.0033 (5) | 0.0006 (5) |
C4 | 0.0339 (7) | 0.0656 (10) | 0.0712 (11) | −0.0018 (7) | 0.0012 (7) | 0.0215 (8) |
C5 | 0.0398 (7) | 0.0332 (6) | 0.0422 (7) | −0.0002 (5) | −0.0004 (5) | −0.0056 (5) |
C6 | 0.0434 (7) | 0.0318 (6) | 0.0382 (7) | 0.0008 (5) | 0.0029 (5) | −0.0035 (5) |
C7 | 0.0427 (7) | 0.0374 (7) | 0.0448 (8) | 0.0016 (5) | 0.0030 (6) | 0.0015 (6) |
C8 | 0.0423 (7) | 0.0432 (8) | 0.0505 (8) | −0.0018 (6) | 0.0076 (6) | −0.0016 (6) |
C9 | 0.0559 (8) | 0.0335 (7) | 0.0499 (8) | −0.0026 (6) | 0.0149 (6) | −0.0013 (6) |
C10 | 0.0564 (9) | 0.0375 (7) | 0.0609 (10) | 0.0076 (6) | 0.0017 (7) | 0.0075 (7) |
C11 | 0.0440 (7) | 0.0394 (7) | 0.0571 (9) | 0.0024 (6) | −0.0015 (6) | 0.0025 (6) |
C12 | 0.0639 (10) | 0.0538 (10) | 0.1031 (16) | −0.0128 (8) | 0.0312 (10) | 0.0093 (9) |
Geometric parameters (Å, º) top
N1—C2 | 1.2810 (16) | C4—H4B | 0.96 |
N2—C3 | 1.2852 (16) | C4—H4C | 0.96 |
N2—N3 | 1.3767 (15) | C5—C6 | 1.4846 (18) |
N3—C5 | 1.3537 (17) | C6—C7 | 1.3877 (19) |
O1—N1 | 1.3978 (15) | C6—C11 | 1.3905 (19) |
O2—C5 | 1.2280 (15) | C7—C8 | 1.3868 (19) |
O3—C9 | 1.3605 (17) | C7—H7 | 0.93 |
O3—C12 | 1.422 (2) | C8—C9 | 1.384 (2) |
N3—H13 | 0.86 | C8—H8 | 0.93 |
O1—H14 | 0.850 (9) | C9—C10 | 1.387 (2) |
C1—C2 | 1.4933 (18) | C10—C11 | 1.372 (2) |
C1—H1A | 0.96 | C10—H10 | 0.93 |
C1—H1B | 0.96 | C11—H11 | 0.93 |
C1—H1C | 0.96 | C12—H12A | 0.96 |
C2—C3 | 1.4786 (18) | C12—H12B | 0.96 |
C3—C4 | 1.5006 (18) | C12—H12C | 0.96 |
C4—H4A | 0.96 | ||
N1—C2—C1 | 125.22 (12) | C5—N3—H13 | 119.8 |
N1—C2—C3 | 113.87 (11) | C6—C7—H7 | 119.3 |
N2—C3—C2 | 115.77 (11) | C6—C11—H11 | 119.3 |
N2—C3—C4 | 125.07 (12) | C7—C6—C5 | 124.44 (11) |
N3—C5—C6 | 116.05 (11) | C7—C6—C11 | 118.03 (12) |
O2—C5—N3 | 122.42 (12) | C7—C8—H8 | 120.3 |
O2—C5—C6 | 121.49 (12) | C8—C7—C6 | 121.38 (12) |
O3—C9—C8 | 124.68 (13) | C8—C7—H7 | 119.3 |
O3—C9—C10 | 115.27 (13) | C8—C9—C10 | 120.04 (13) |
C2—N1—O1 | 113.16 (10) | C9—C8—C7 | 119.31 (12) |
C3—N2—N3 | 115.85 (10) | C9—C8—H8 | 120.3 |
C5—N3—N2 | 120.43 (11) | C9—C10—H10 | 120.1 |
C9—O3—C12 | 118.29 (13) | C10—C11—C6 | 121.36 (13) |
N1—O1—H14 | 101.6 (14) | C10—C11—H11 | 119.3 |
N2—N3—H13 | 119.8 | C11—C6—C5 | 117.50 (12) |
O3—C12—H12A | 109.5 | C11—C10—C9 | 119.88 (13) |
O3—C12—H12B | 109.5 | C11—C10—H10 | 120.1 |
O3—C12—H12C | 109.5 | H1A—C1—H1B | 109.5 |
C2—C1—H1C | 109.5 | H1A—C1—H1C | 109.5 |
C2—C1—H1A | 109.5 | H1B—C1—H1C | 109.5 |
C2—C1—H1B | 109.5 | H4A—C4—H4B | 109.5 |
C2—C3—C4 | 119.14 (11) | H4A—C4—H4C | 109.5 |
C3—C2—C1 | 120.91 (11) | H4B—C4—H4C | 109.5 |
C3—C4—H4A | 109.5 | H12A—C12—H12B | 109.5 |
C3—C4—H4B | 109.5 | H12A—C12—H12C | 109.5 |
C3—C4—H4C | 109.5 | H12B—C12—H12C | 109.5 |
N1—C2—C3—N2 | −174.00 (12) | C1—C2—C3—C4 | −172.84 (14) |
N1—C2—C3—C4 | 7.35 (19) | C3—N2—N3—C5 | 170.08 (13) |
N2—N3—C5—O2 | 0.7 (2) | C5—C6—C7—C8 | 177.33 (12) |
N2—N3—C5—C6 | −177.14 (11) | C5—C6—C11—C10 | −177.91 (13) |
N3—N2—C3—C2 | 178.01 (11) | C6—C7—C8—C9 | 0.3 (2) |
N3—N2—C3—C4 | −3.4 (2) | C7—C6—C11—C10 | 0.0 (2) |
N3—C5—C6—C7 | 12.42 (19) | C7—C8—C9—O3 | −179.88 (13) |
N3—C5—C6—C11 | −169.82 (13) | C7—C8—C9—C10 | 0.2 (2) |
O1—N1—C2—C1 | 0.7 (2) | C8—C9—C10—C11 | −0.6 (2) |
O1—N1—C2—C3 | −179.47 (11) | C9—C10—C11—C6 | 0.5 (2) |
O2—C5—C6—C7 | −165.48 (13) | C11—C6—C7—C8 | −0.4 (2) |
O2—C5—C6—C11 | 12.3 (2) | C12—O3—C9—C8 | −4.9 (2) |
O3—C9—C10—C11 | 179.46 (14) | C12—O3—C9—C10 | 175.07 (15) |
C1—C2—C3—N2 | 5.80 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H14···O2i | 0.85 (1) | 1.84 (1) | 2.683 (1) | 168 (2) |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
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