The title compound, C
10H
11N
5O
5, contains of dinitrophenyl, monooxime and hydrazone groups. The molecules are linked through O—H
N and C—H
O hydrogen bonds. There are also π–π interactions and intramolecular hydrogen bonds. All these hydrogen bonds are highly effective in forming dimeric chains, thereby stabilizing the crystal structure. The monooxime and hydrazone groups both have an
E configuration.
Supporting information
CCDC reference: 248774
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.132
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.102
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime
top
Crystal data top
C10H11N5O5 | F(000) = 584 |
Mr = 281.24 | Dx = 1.503 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 10.1400 (16) Å | Cell parameters from 8500 reflections |
b = 12.3079 (19) Å | θ = 2.0–26.8° |
c = 10.6624 (18) Å | µ = 0.12 mm−1 |
β = 110.950 (12)° | T = 293 K |
V = 1242.7 (3) Å3 | Prism, orange |
Z = 4 | 0.35 × 0.23 × 0.12 mm |
Data collection top
Stoe IPDS-2 diffractometer | 1207 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.103 |
Plane graphite monochromator | θmax = 25.0°, θmin = 2.2° |
Detector resolution: 6.67 pixels mm-1 | h = −12→11 |
rotation method scans | k = −14→14 |
12323 measured reflections | l = −12→12 |
2180 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0738P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max < 0.001 |
2180 reflections | Δρmax = 0.20 e Å−3 |
188 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (4) |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.0765 (3) | 0.43607 (17) | 0.1334 (2) | 0.0612 (6) | |
N2 | 0.2179 (2) | 0.20795 (17) | 0.3256 (2) | 0.0524 (6) | |
N3 | 0.2115 (3) | 0.09776 (18) | 0.3044 (2) | 0.0546 (6) | |
N4 | 0.1859 (3) | −0.13339 (19) | 0.2505 (2) | 0.0607 (6) | |
N5 | 0.4683 (3) | −0.2005 (2) | 0.7159 (3) | 0.0667 (7) | |
O1 | 0.0878 (2) | 0.54816 (15) | 0.1548 (2) | 0.0796 (7) | |
H1 | 0.0399 | 0.5797 | 0.0858 | 0.119* | |
O2 | 0.1342 (3) | −0.07263 (17) | 0.1538 (2) | 0.0860 (7) | |
O3 | 0.1729 (2) | −0.23197 (16) | 0.2397 (2) | 0.0844 (7) | |
O4 | 0.4565 (3) | −0.2972 (2) | 0.6883 (2) | 0.0889 (7) | |
O5 | 0.5320 (3) | −0.1659 (2) | 0.8274 (2) | 0.0997 (8) | |
C1 | 0.1509 (3) | 0.3830 (2) | 0.2396 (3) | 0.0533 (7) | |
C2 | 0.1439 (3) | 0.2642 (2) | 0.2222 (3) | 0.0525 (7) | |
C3 | 0.2746 (3) | 0.0255 (2) | 0.4041 (2) | 0.0466 (6) | |
C4 | 0.2634 (3) | −0.0874 (2) | 0.3819 (2) | 0.0486 (6) | |
C5 | 0.3275 (3) | −0.1608 (2) | 0.4837 (3) | 0.0530 (7) | |
H5 | 0.3200 | −0.2351 | 0.4671 | 0.064* | |
C6 | 0.4014 (3) | −0.1221 (2) | 0.6082 (3) | 0.0505 (7) | |
C7 | 0.4155 (3) | −0.0113 (2) | 0.6347 (3) | 0.0520 (7) | |
H7 | 0.4677 | 0.0131 | 0.7208 | 0.062* | |
C8 | 0.3534 (3) | 0.0614 (2) | 0.5357 (2) | 0.0488 (6) | |
H8 | 0.3628 | 0.1354 | 0.5543 | 0.059* | |
C9 | 0.2386 (3) | 0.4336 (2) | 0.3680 (3) | 0.0708 (8) | |
H9A | 0.2936 | 0.4913 | 0.3508 | 0.106* | |
H9B | 0.3006 | 0.3800 | 0.4244 | 0.106* | |
H9C | 0.1787 | 0.4624 | 0.4122 | 0.106* | |
C10 | 0.0540 (4) | 0.2172 (3) | 0.0902 (3) | 0.0781 (9) | |
H10A | 0.1131 | 0.1909 | 0.0438 | 0.117* | |
H10B | −0.0081 | 0.2723 | 0.0372 | 0.117* | |
H10C | −0.0008 | 0.1583 | 0.1049 | 0.117* | |
H3 | 0.166 (3) | 0.071 (2) | 0.228 (3) | 0.076 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0708 (17) | 0.0440 (13) | 0.0734 (16) | 0.0067 (11) | 0.0316 (13) | 0.0123 (11) |
N2 | 0.0577 (14) | 0.0421 (12) | 0.0579 (13) | 0.0008 (10) | 0.0213 (11) | 0.0034 (10) |
N3 | 0.0645 (16) | 0.0453 (13) | 0.0485 (13) | 0.0032 (11) | 0.0136 (11) | 0.0023 (11) |
N4 | 0.0660 (16) | 0.0523 (14) | 0.0581 (14) | −0.0037 (12) | 0.0153 (12) | −0.0051 (12) |
N5 | 0.0694 (17) | 0.0660 (18) | 0.0627 (16) | 0.0060 (14) | 0.0210 (13) | 0.0178 (14) |
O1 | 0.0957 (17) | 0.0458 (12) | 0.1002 (16) | 0.0107 (11) | 0.0387 (14) | 0.0163 (11) |
O2 | 0.1177 (19) | 0.0608 (13) | 0.0543 (12) | 0.0020 (12) | −0.0002 (11) | −0.0018 (11) |
O3 | 0.1091 (18) | 0.0487 (13) | 0.0802 (14) | −0.0117 (12) | 0.0152 (12) | −0.0117 (11) |
O4 | 0.1108 (19) | 0.0557 (14) | 0.0930 (16) | 0.0105 (13) | 0.0275 (14) | 0.0213 (12) |
O5 | 0.128 (2) | 0.0914 (18) | 0.0556 (14) | 0.0020 (15) | 0.0040 (13) | 0.0168 (13) |
C1 | 0.0553 (17) | 0.0516 (15) | 0.0568 (16) | 0.0033 (13) | 0.0245 (13) | 0.0085 (13) |
C2 | 0.0597 (18) | 0.0474 (15) | 0.0514 (15) | 0.0015 (13) | 0.0210 (13) | 0.0041 (12) |
C3 | 0.0468 (16) | 0.0451 (15) | 0.0498 (14) | 0.0011 (11) | 0.0196 (12) | 0.0013 (12) |
C4 | 0.0515 (16) | 0.0432 (15) | 0.0494 (14) | −0.0031 (11) | 0.0161 (12) | −0.0016 (12) |
C5 | 0.0548 (16) | 0.0431 (14) | 0.0638 (16) | −0.0015 (13) | 0.0243 (13) | 0.0026 (13) |
C6 | 0.0525 (16) | 0.0484 (16) | 0.0515 (15) | 0.0019 (13) | 0.0195 (13) | 0.0080 (12) |
C7 | 0.0539 (17) | 0.0545 (17) | 0.0482 (15) | −0.0019 (13) | 0.0190 (13) | −0.0032 (13) |
C8 | 0.0524 (16) | 0.0434 (14) | 0.0528 (15) | 0.0025 (13) | 0.0213 (13) | 0.0006 (12) |
C9 | 0.088 (2) | 0.0558 (18) | 0.0667 (18) | −0.0013 (16) | 0.0247 (16) | 0.0000 (15) |
C10 | 0.100 (3) | 0.0606 (19) | 0.0606 (18) | 0.0115 (17) | 0.0124 (17) | 0.0031 (15) |
Geometric parameters (Å, º) top
N1—C1 | 1.292 (3) | C3—C4 | 1.408 (3) |
N1—O1 | 1.396 (3) | C3—C8 | 1.414 (3) |
N2—C2 | 1.290 (3) | C4—C5 | 1.382 (4) |
N2—N3 | 1.373 (3) | C5—C6 | 1.356 (4) |
N3—C3 | 1.358 (3) | C5—H5 | 0.9300 |
N3—H3 | 0.85 (3) | C6—C7 | 1.390 (4) |
N4—O3 | 1.221 (3) | C7—C8 | 1.355 (3) |
N4—O2 | 1.229 (3) | C7—H7 | 0.9300 |
N4—C4 | 1.454 (3) | C8—H8 | 0.9300 |
N5—O5 | 1.210 (3) | C9—H9A | 0.9600 |
N5—O4 | 1.222 (3) | C9—H9B | 0.9600 |
N5—C6 | 1.467 (3) | C9—H9C | 0.9600 |
O1—H1 | 0.8200 | C10—H10A | 0.9600 |
C1—C2 | 1.473 (4) | C10—H10B | 0.9600 |
C1—C9 | 1.477 (4) | C10—H10C | 0.9600 |
C2—C10 | 1.492 (4) | | |
| | | |
C1—N1—O1 | 111.6 (2) | C6—C5—C4 | 118.6 (2) |
C2—N2—N3 | 114.2 (2) | C6—C5—H5 | 120.7 |
C3—N3—N2 | 122.5 (2) | C4—C5—H5 | 120.7 |
C3—N3—H3 | 116 (2) | C5—C6—C7 | 121.6 (2) |
N2—N3—H3 | 121 (2) | C5—C6—N5 | 118.3 (2) |
O3—N4—O2 | 121.7 (2) | C7—C6—N5 | 120.1 (3) |
O3—N4—C4 | 118.7 (2) | C8—C7—C6 | 120.2 (2) |
O2—N4—C4 | 119.6 (2) | C8—C7—H7 | 119.9 |
O5—N5—O4 | 123.5 (3) | C6—C7—H7 | 119.9 |
O5—N5—C6 | 118.2 (3) | C7—C8—C3 | 120.5 (2) |
O4—N5—C6 | 118.3 (3) | C7—C8—H8 | 119.8 |
N1—O1—H1 | 109.5 | C3—C8—H8 | 119.8 |
N1—C1—C2 | 113.9 (3) | C1—C9—H9A | 109.5 |
N1—C1—C9 | 124.7 (2) | C1—C9—H9B | 109.5 |
C2—C1—C9 | 121.4 (2) | H9A—C9—H9B | 109.5 |
N2—C2—C1 | 115.9 (2) | C1—C9—H9C | 109.5 |
N2—C2—C10 | 124.8 (2) | H9A—C9—H9C | 109.5 |
C1—C2—C10 | 119.3 (3) | H9B—C9—H9C | 109.5 |
N3—C3—C4 | 121.9 (2) | C2—C10—H10A | 109.5 |
N3—C3—C8 | 120.9 (2) | C2—C10—H10B | 109.5 |
C4—C3—C8 | 117.3 (2) | H10A—C10—H10B | 109.5 |
C5—C4—C3 | 121.7 (2) | C2—C10—H10C | 109.5 |
C5—C4—N4 | 116.3 (2) | H10A—C10—H10C | 109.5 |
C3—C4—N4 | 122.0 (2) | H10B—C10—H10C | 109.5 |
| | | |
C2—N2—N3—C3 | −175.4 (2) | O2—N4—C4—C5 | −175.3 (2) |
O1—N1—C1—C2 | −179.47 (19) | O3—N4—C4—C3 | −175.5 (2) |
O1—N1—C1—C9 | −0.6 (4) | O2—N4—C4—C3 | 3.8 (4) |
N3—N2—C2—C1 | −178.4 (2) | C3—C4—C5—C6 | 0.7 (4) |
N3—N2—C2—C10 | 1.8 (4) | N4—C4—C5—C6 | 179.8 (2) |
N1—C1—C2—N2 | 179.3 (2) | C4—C5—C6—C7 | −0.9 (4) |
C9—C1—C2—N2 | 0.4 (4) | C4—C5—C6—N5 | 179.6 (2) |
N1—C1—C2—C10 | −0.9 (4) | O5—N5—C6—C5 | −178.7 (3) |
C9—C1—C2—C10 | −179.8 (3) | O4—N5—C6—C5 | 1.2 (4) |
N2—N3—C3—C4 | 178.0 (2) | O5—N5—C6—C7 | 1.8 (4) |
N2—N3—C3—C8 | −1.4 (4) | O4—N5—C6—C7 | −178.4 (3) |
N3—C3—C4—C5 | −179.9 (2) | C5—C6—C7—C8 | 0.7 (4) |
C8—C3—C4—C5 | −0.5 (4) | N5—C6—C7—C8 | −179.7 (2) |
N3—C3—C4—N4 | 1.1 (4) | C6—C7—C8—C3 | −0.4 (4) |
C8—C3—C4—N4 | −179.5 (2) | N3—C3—C8—C7 | 179.7 (2) |
O3—N4—C4—C5 | 5.4 (4) | C4—C3—C8—C7 | 0.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.22 | 2.932 (3) | 146 |
C7—H7···O4ii | 0.93 | 2.54 | 3.230 (4) | 131 |
N3—H3···O2 | 0.85 (3) | 1.92 (3) | 2.587 (3) | 135 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y+1/2, −z+3/2. |
Comparative geometrical parameters (Å, °) in the hydrazone moiety
of (I) with those in the related compounds (II),(III) and (IV) topBonds | (I) | (II) | (III) | (IV) |
N3—C3 | 1.358 (3) | 1.356 (2) | 1.343 (3) | 1.351 (3) |
N2—N3 | 1.373 (3) | 1.3714 (18) | 1.379 (3) | 1.367 (3) |
N2—C2 | 1.290 (3) | 1.276 (2) | 1.289 (3) | 1.286 (3) |
| | | | |
C3—N3—N2 | 122.5 (2) | 116.11 (13) | 119.1 (2) | 120.39 (19) |
C2—N2—N3 | 114.2 (2) | 116.83 (14) | 117.0 (2) | 116.7 (2) |