3-[(2,4-Di­nitro­phenyl)­hydrazono]­butan-2-one oxime

Saraçoğlu, H.; Davran, C.; Soylu, S.; Andaç, Ö.; Batı, H.; Çalışkan, N.

doi:10.1107/S1600536804015235

3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime

H. Saraçoğlu, C. Davran, S. Soylu, Ö. Andaç, H. Batı and N. Çalışkan

The title compound, C₁₀H₁₁N₅O₅, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015235/rn6016sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015235/rn6016Isup2.hkl Contains datablock I

CCDC reference: 248774

checkCIF report

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

Computing details top

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
M_r = 281.24	D_x = 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	R_int = 0.103
Plane graphite monochromator	θ_max = 25.0°, θ_min = 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(F_o²) + (0.0738P)²] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max < 0.001
2180 reflections	Δρ_max = 0.20 e Å⁻³
188 parameters	Δρ_min = −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	U_iso*/U_eq
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) top

Bonds	(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)

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3-[(2,4-Di­nitro­phenyl)­hydrazono]­butan-2-one oxime

Supporting information

Key indicators

checkCIF/PLATON results

3-[(2,4-Dinitrophenyl)hydrazono]butan-2-one oxime