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In the title molecule, C
15H
17N
5O
3, the nitro group lies in the plane of the imidazole group, which makes a dihedral angle of 59.9 (2)° with the benzene ring. Intermolecular N—H
O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing is further stabilized by weak C—H
O and C—H
N interactions.
Supporting information
CCDC reference: 601790
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.065
- wR factor = 0.256
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.256
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg 89.46 Deg.
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C24
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C16
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Farrugia, 1999); program(s) used to solve structure: SIR2004 (Burla et al., 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
4-Methylacetophenone [(2-methyl-4-nitro-1
H-imidazol-1-yl)acetyl]hydrazone
top
Crystal data top
C15H17N5O3 | F(000) = 664 |
Mr = 315.34 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/c | Melting point = 524–525 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54180 Å |
a = 8.423 (2) Å | Cell parameters from 25 reflections |
b = 10.577 (4) Å | θ = 15–25° |
c = 17.97 (3) Å | µ = 0.78 mm−1 |
β = 89.46 (8)° | T = 298 K |
V = 1601 (3) Å3 | Plate, colourless |
Z = 4 | 0.3 × 0.1 × 0.1 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2512 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 68.0°, θmin = 4.9° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
Tmin = 0.799, Tmax = 0.926 | l = −21→21 |
3111 measured reflections | 2 standard reflections every 60 min |
2902 independent reflections | intensity decay: none |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.256 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.1295P)2 + 1.2895P] where P = (Fo2 + 2Fc2)/3 |
2902 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O12 | 0.4591 (4) | 1.0360 (2) | 0.08760 (15) | 0.0761 (10) | |
O41 | −0.0500 (4) | 1.2251 (3) | 0.2636 (3) | 0.1033 (16) | |
O42 | 0.1268 (4) | 1.3437 (3) | 0.31357 (19) | 0.0825 (11) | |
N1 | 0.3216 (3) | 0.9911 (2) | 0.21945 (14) | 0.0478 (8) | |
N3 | 0.3600 (3) | 1.1705 (3) | 0.27901 (17) | 0.0575 (10) | |
N4 | 0.0868 (4) | 1.2472 (3) | 0.28163 (18) | 0.0611 (10) | |
N13 | 0.4002 (4) | 0.8454 (3) | 0.03981 (16) | 0.0593 (10) | |
N14 | 0.3374 (3) | 0.7258 (2) | 0.05162 (16) | 0.0536 (9) | |
C2 | 0.4307 (4) | 1.0689 (3) | 0.25197 (17) | 0.0498 (10) | |
C4 | 0.2055 (4) | 1.1548 (3) | 0.26327 (19) | 0.0525 (11) | |
C5 | 0.1775 (4) | 1.0444 (3) | 0.22681 (19) | 0.0502 (10) | |
C11 | 0.3546 (4) | 0.8815 (3) | 0.17312 (18) | 0.0520 (10) | |
C12 | 0.4085 (4) | 0.9265 (3) | 0.09706 (18) | 0.0539 (10) | |
C15 | 0.3305 (4) | 0.6525 (3) | −0.0052 (2) | 0.0592 (11) | |
C16 | 0.3859 (6) | 0.6823 (4) | −0.0796 (2) | 0.0804 (18) | |
C17 | 0.2593 (4) | 0.5240 (3) | 0.01097 (19) | 0.0585 (11) | |
C18 | 0.2877 (5) | 0.4236 (4) | −0.0378 (2) | 0.0720 (14) | |
C19 | 0.2214 (6) | 0.3092 (4) | −0.0232 (3) | 0.0865 (18) | |
C20 | 0.1185 (5) | 0.2868 (3) | 0.0385 (3) | 0.0725 (15) | |
C21 | 0.0926 (5) | 0.3889 (4) | 0.0839 (3) | 0.0716 (14) | |
C22 | 0.1591 (5) | 0.5055 (3) | 0.0710 (2) | 0.0636 (11) | |
C23 | 0.0406 (7) | 0.1624 (4) | 0.0473 (4) | 0.102 (2) | |
C24 | 0.6011 (5) | 1.0395 (4) | 0.2551 (3) | 0.0750 (16) | |
H5 | 0.08064 | 1.01301 | 0.21064 | 0.0602* | |
H11A | 0.43694 | 0.83032 | 0.19555 | 0.0623* | |
H11B | 0.25981 | 0.83010 | 0.16862 | 0.0623* | |
H13 | 0.43347 | 0.86733 | −0.00371 | 0.0713* | |
H16A | 0.49766 | 0.69985 | −0.07857 | 0.1201* | |
H16B | 0.36662 | 0.61165 | −0.11181 | 0.1201* | |
H16C | 0.33021 | 0.75506 | −0.09768 | 0.1201* | |
H18 | 0.35144 | 0.43504 | −0.07978 | 0.0864* | |
H19 | 0.24430 | 0.24228 | −0.05519 | 0.1041* | |
H21 | 0.02693 | 0.37881 | 0.12538 | 0.0861* | |
H22 | 0.13630 | 0.57231 | 0.10303 | 0.0765* | |
H23A | 0.07799 | 0.10611 | 0.00903 | 0.1524* | |
H23B | 0.06537 | 0.12792 | 0.09519 | 0.1524* | |
H23C | −0.07231 | 0.17239 | 0.04325 | 0.1524* | |
H24A | 0.62064 | 0.95939 | 0.23157 | 0.1120* | |
H24B | 0.66027 | 1.10418 | 0.22965 | 0.1120* | |
H24C | 0.63366 | 1.03557 | 0.30611 | 0.1120* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O12 | 0.124 (2) | 0.0447 (14) | 0.0592 (15) | −0.0217 (14) | 0.0161 (14) | −0.0018 (12) |
O41 | 0.0594 (18) | 0.088 (2) | 0.162 (4) | 0.0102 (15) | 0.0142 (19) | −0.026 (2) |
O42 | 0.098 (2) | 0.0545 (17) | 0.095 (2) | 0.0159 (14) | 0.0031 (16) | −0.0164 (15) |
N1 | 0.0620 (16) | 0.0339 (13) | 0.0473 (14) | −0.0063 (11) | 0.0037 (11) | −0.0038 (10) |
N3 | 0.0639 (17) | 0.0463 (16) | 0.0621 (18) | 0.0013 (12) | 0.0037 (13) | −0.0082 (13) |
N4 | 0.0696 (19) | 0.0400 (16) | 0.0734 (19) | 0.0039 (13) | 0.0100 (14) | −0.0011 (14) |
N13 | 0.090 (2) | 0.0371 (14) | 0.0507 (16) | −0.0131 (13) | 0.0103 (14) | −0.0089 (12) |
N14 | 0.0768 (18) | 0.0319 (13) | 0.0521 (15) | −0.0008 (12) | −0.0010 (13) | 0.0007 (11) |
C2 | 0.0651 (18) | 0.0395 (16) | 0.0449 (16) | −0.0009 (13) | −0.0052 (13) | 0.0038 (13) |
C4 | 0.0602 (19) | 0.0397 (17) | 0.0574 (19) | 0.0003 (13) | 0.0073 (14) | −0.0028 (14) |
C5 | 0.0524 (17) | 0.0400 (16) | 0.0579 (18) | −0.0064 (13) | 0.0062 (13) | 0.0024 (14) |
C11 | 0.070 (2) | 0.0378 (16) | 0.0482 (17) | −0.0047 (14) | 0.0043 (14) | 0.0008 (13) |
C12 | 0.078 (2) | 0.0329 (16) | 0.0507 (18) | −0.0032 (14) | 0.0087 (15) | −0.0033 (13) |
C15 | 0.076 (2) | 0.0469 (19) | 0.0546 (19) | 0.0000 (15) | −0.0034 (16) | −0.0097 (15) |
C16 | 0.123 (4) | 0.072 (3) | 0.046 (2) | −0.012 (2) | 0.001 (2) | −0.0156 (18) |
C17 | 0.077 (2) | 0.0494 (19) | 0.0493 (18) | 0.0018 (16) | −0.0131 (16) | −0.0085 (15) |
C18 | 0.097 (3) | 0.049 (2) | 0.070 (2) | 0.0100 (19) | −0.010 (2) | −0.0082 (18) |
C19 | 0.106 (3) | 0.051 (2) | 0.103 (4) | 0.004 (2) | −0.029 (3) | −0.020 (2) |
C20 | 0.099 (3) | 0.0332 (18) | 0.086 (3) | −0.0009 (17) | −0.036 (2) | −0.0040 (17) |
C21 | 0.092 (3) | 0.049 (2) | 0.074 (2) | −0.0074 (19) | −0.016 (2) | −0.0005 (19) |
C22 | 0.080 (2) | 0.0417 (18) | 0.069 (2) | 0.0021 (16) | −0.0048 (18) | −0.0064 (16) |
C23 | 0.141 (5) | 0.037 (2) | 0.128 (4) | −0.011 (2) | −0.040 (4) | 0.003 (2) |
C24 | 0.067 (2) | 0.068 (3) | 0.090 (3) | 0.0099 (18) | −0.006 (2) | −0.023 (2) |
Geometric parameters (Å, º) top
O12—C12 | 1.245 (4) | C19—C20 | 1.421 (8) |
O41—N4 | 1.222 (5) | C20—C23 | 1.478 (6) |
O42—N4 | 1.220 (5) | C20—C21 | 1.370 (7) |
N1—C2 | 1.369 (5) | C21—C22 | 1.373 (6) |
N1—C5 | 1.344 (5) | C5—H5 | 0.9300 |
N1—C11 | 1.453 (5) | C11—H11A | 0.9700 |
N3—C2 | 1.319 (5) | C11—H11B | 0.9700 |
N3—C4 | 1.345 (5) | C16—H16A | 0.9600 |
N4—C4 | 1.434 (5) | C16—H16B | 0.9600 |
N13—N14 | 1.387 (5) | C16—H16C | 0.9600 |
N13—C12 | 1.342 (5) | C18—H18 | 0.9300 |
N14—C15 | 1.284 (5) | C19—H19 | 0.9300 |
N13—H13 | 0.8600 | C21—H21 | 0.9300 |
C2—C24 | 1.470 (6) | C22—H22 | 0.9300 |
C4—C5 | 1.361 (5) | C23—H23A | 0.9600 |
C11—C12 | 1.513 (5) | C23—H23B | 0.9600 |
C15—C16 | 1.447 (6) | C23—H23C | 0.9600 |
C15—C17 | 1.513 (5) | C24—H24A | 0.9600 |
C17—C22 | 1.377 (6) | C24—H24B | 0.9600 |
C17—C18 | 1.396 (6) | C24—H24C | 0.9600 |
C18—C19 | 1.357 (7) | | |
| | | |
O12···N1 | 2.670 (6) | C18···H16B | 2.4800 |
O12···C2 | 2.982 (6) | C19···H16Aviii | 3.0100 |
O12···C24 | 3.250 (8) | C22···H24Cvii | 2.8500 |
O12···N13i | 2.858 (6) | C24···H11A | 2.8200 |
O12···C16i | 3.256 (7) | H5···O41 | 2.6700 |
O41···C11ii | 3.249 (7) | H5···H11B | 2.5600 |
O42···N3 | 2.753 (6) | H5···H23Bx | 2.4100 |
O42···C5ii | 3.411 (7) | H5···O42vi | 2.5400 |
O42···C24iii | 3.318 (8) | H11A···N14 | 2.9400 |
O12···H16Ci | 2.8400 | H11A···C24 | 2.8200 |
O12···H13i | 2.0300 | H11A···H24A | 2.1700 |
O12···H16Ai | 2.8200 | H11A···N3vii | 2.4500 |
O41···H5 | 2.6700 | H11B···N14 | 2.4600 |
O41···H24Biv | 2.8300 | H11B···H5 | 2.5600 |
O41···H11Bii | 2.4100 | H11B···O41vi | 2.4100 |
O42···H5ii | 2.5400 | H13···C16 | 2.4200 |
O42···H24Aiii | 2.5800 | H13···H16A | 2.2900 |
O42···H19v | 2.7200 | H13···H16C | 2.2500 |
N1···O12 | 2.670 (6) | H13···O12i | 2.0300 |
N3···O42 | 2.753 (6) | H13···C12i | 3.0500 |
N3···C11iii | 3.397 (7) | H16A···N13 | 2.7500 |
N13···O12i | 2.858 (6) | H16A···H13 | 2.2900 |
N3···H11Aiii | 2.4500 | H16A···O12i | 2.8200 |
N3···H18v | 2.7700 | H16A···C18viii | 3.0700 |
N13···H16A | 2.7500 | H16A···C19viii | 3.0100 |
N13···H16C | 2.7200 | H16B···C18 | 2.4800 |
N14···H11A | 2.9400 | H16B···H18 | 1.9600 |
N14···H11B | 2.4600 | H16C···N13 | 2.7200 |
N14···H22 | 2.5200 | H16C···H13 | 2.2500 |
C2···O12 | 2.982 (6) | H16C···O12i | 2.8400 |
C5···O42vi | 3.411 (7) | H16C···H23Cix | 2.4900 |
C11···O41vi | 3.249 (7) | H18···C16 | 2.6300 |
C11···N3vii | 3.397 (7) | H18···H16B | 1.9600 |
C12···C24 | 3.495 (8) | H18···N3xi | 2.7700 |
C15···C18viii | 3.411 (8) | H18···C2xi | 3.0900 |
C16···O12i | 3.256 (7) | H19···H23A | 2.3100 |
C17···C21ix | 3.555 (8) | H19···O42xi | 2.7200 |
C18···C15viii | 3.411 (8) | H22···N14 | 2.5200 |
C21···C17ix | 3.555 (8) | H22···H24Cvii | 2.5800 |
C24···O12 | 3.250 (8) | H23A···H19 | 2.3100 |
C24···C12 | 3.495 (8) | H23B···C5xii | 2.7000 |
C24···O42vii | 3.318 (8) | H23B···H5xii | 2.4100 |
C2···H18v | 3.0900 | H23C···C15ix | 2.9400 |
C5···H23Bx | 2.7000 | H23C···H16Cix | 2.4900 |
C11···H24A | 2.6200 | H24A···C11 | 2.6200 |
C12···H13i | 3.0500 | H24A···C12 | 3.0400 |
C12···H24A | 3.0400 | H24A···H11A | 2.1700 |
C15···H23Cix | 2.9400 | H24A···O42vii | 2.5800 |
C16···H13 | 2.4200 | H24B···O41xiii | 2.8300 |
C16···H18 | 2.6300 | H24C···C22iii | 2.8500 |
C18···H16Aviii | 3.0700 | H24C···H22iii | 2.5800 |
| | | |
C2—N1—C5 | 108.4 (3) | C17—C22—C21 | 120.4 (4) |
C2—N1—C11 | 126.8 (3) | N1—C5—H5 | 128.00 |
C5—N1—C11 | 124.0 (3) | C4—C5—H5 | 128.00 |
C2—N3—C4 | 104.9 (3) | N1—C11—H11A | 110.00 |
O41—N4—O42 | 123.4 (4) | N1—C11—H11B | 110.00 |
O41—N4—C4 | 117.7 (3) | C12—C11—H11A | 110.00 |
O42—N4—C4 | 118.9 (3) | C12—C11—H11B | 110.00 |
N14—N13—C12 | 119.2 (3) | H11A—C11—H11B | 108.00 |
N13—N14—C15 | 116.7 (3) | C15—C16—H16A | 109.00 |
C12—N13—H13 | 120.00 | C15—C16—H16B | 109.00 |
N14—N13—H13 | 120.00 | C15—C16—H16C | 109.00 |
N1—C2—C24 | 123.3 (3) | H16A—C16—H16B | 109.00 |
N1—C2—N3 | 110.2 (3) | H16A—C16—H16C | 110.00 |
N3—C2—C24 | 126.6 (3) | H16B—C16—H16C | 110.00 |
N3—C4—C5 | 112.3 (3) | C17—C18—H18 | 120.00 |
N4—C4—C5 | 124.9 (3) | C19—C18—H18 | 120.00 |
N3—C4—N4 | 122.8 (3) | C18—C19—H19 | 118.00 |
N1—C5—C4 | 104.3 (3) | C20—C19—H19 | 118.00 |
N1—C11—C12 | 108.7 (3) | C20—C21—H21 | 118.00 |
O12—C12—N13 | 120.7 (3) | C22—C21—H21 | 118.00 |
N13—C12—C11 | 118.3 (3) | C17—C22—H22 | 120.00 |
O12—C12—C11 | 121.0 (3) | C21—C22—H22 | 120.00 |
N14—C15—C17 | 114.3 (3) | C20—C23—H23A | 109.00 |
C16—C15—C17 | 119.8 (3) | C20—C23—H23B | 110.00 |
N14—C15—C16 | 125.9 (3) | C20—C23—H23C | 109.00 |
C18—C17—C22 | 118.9 (3) | H23A—C23—H23B | 110.00 |
C15—C17—C18 | 119.8 (3) | H23A—C23—H23C | 109.00 |
C15—C17—C22 | 121.1 (3) | H23B—C23—H23C | 109.00 |
C17—C18—C19 | 119.3 (4) | C2—C24—H24A | 109.00 |
C18—C19—C20 | 123.1 (4) | C2—C24—H24B | 109.00 |
C19—C20—C23 | 119.9 (4) | C2—C24—H24C | 109.00 |
C19—C20—C21 | 115.2 (4) | H24A—C24—H24B | 109.00 |
C21—C20—C23 | 124.8 (5) | H24A—C24—H24C | 109.00 |
C20—C21—C22 | 123.0 (4) | H24B—C24—H24C | 110.00 |
| | | |
C5—N1—C2—N3 | −0.7 (4) | N13—N14—C15—C17 | −179.4 (3) |
C5—N1—C2—C24 | 179.3 (4) | N3—C4—C5—N1 | −0.6 (4) |
C11—N1—C2—N3 | 169.1 (3) | N4—C4—C5—N1 | 177.8 (3) |
C11—N1—C2—C24 | −11.0 (5) | N1—C11—C12—O12 | 19.3 (4) |
C2—N1—C5—C4 | 0.7 (4) | N1—C11—C12—N13 | −160.6 (3) |
C11—N1—C5—C4 | −169.4 (3) | N14—C15—C17—C22 | 23.2 (5) |
C2—N1—C11—C12 | −75.3 (4) | C16—C15—C17—C18 | 18.5 (5) |
C5—N1—C11—C12 | 93.0 (4) | N14—C15—C17—C18 | −160.5 (3) |
C4—N3—C2—N1 | 0.3 (4) | C16—C15—C17—C22 | −157.8 (4) |
C4—N3—C2—C24 | −179.6 (4) | C15—C17—C18—C19 | −179.1 (4) |
C2—N3—C4—N4 | −178.2 (3) | C22—C17—C18—C19 | −2.7 (6) |
C2—N3—C4—C5 | 0.2 (4) | C18—C17—C22—C21 | 2.2 (6) |
O41—N4—C4—N3 | 178.6 (4) | C15—C17—C22—C21 | 178.5 (4) |
O41—N4—C4—C5 | 0.4 (6) | C17—C18—C19—C20 | 2.4 (7) |
O42—N4—C4—N3 | −0.8 (5) | C18—C19—C20—C23 | 175.0 (5) |
O42—N4—C4—C5 | −178.9 (4) | C18—C19—C20—C21 | −1.3 (7) |
C12—N13—N14—C15 | 179.2 (3) | C19—C20—C21—C22 | 0.7 (7) |
N14—N13—C12—O12 | −177.5 (3) | C23—C20—C21—C22 | −175.5 (5) |
N14—N13—C12—C11 | 2.4 (5) | C20—C21—C22—C17 | −1.2 (7) |
N13—N14—C15—C16 | 1.7 (5) | | |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2; (iv) x−1, y, z; (v) x, −y+3/2, z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z; (ix) −x, −y+1, −z; (x) x, y+1, z; (xi) x, −y+3/2, z−1/2; (xii) x, y−1, z; (xiii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N13—H13···O12i | 0.86 | 2.03 | 2.858 (6) | 162 |
C5—H5···O42vi | 0.93 | 2.54 | 3.411 (7) | 156 |
C11—H11A···N3vii | 0.97 | 2.45 | 3.397 (7) | 165 |
C11—H11B···O41vi | 0.97 | 2.41 | 3.249 (7) | 145 |
C24—H24A···O42vii | 0.96 | 2.58 | 3.318 (8) | 134 |
Symmetry codes: (i) −x+1, −y+2, −z; (vi) −x, y−1/2, −z+1/2; (vii) −x+1, y−1/2, −z+1/2. |
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