A monoclinic polymorph with Z = 4 of (E)-2,4-dihy­droxy­acetophenone 2,4-dinitro­phenyl­hydrazone N,N-dimethyl­formamide monosolvate

Han, H.; Liu, Y.

doi:10.1107/S1600536811050161

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3434

https://doi.org/10.1107/S1600536811050161

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A monoclinic polymorph with Z = 4 of (E)-2,4-dihydroxyacetophenone 2,4-dinitrophenylhydrazone N,N-dimethylformamide monosolvate

Hongfei Han ^a ^* and Yaohua Liu ^a

^aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: hhf_2222@yahoo.com.cn

(Received 26 October 2011; accepted 22 November 2011; online 25 November 2011)

The title compound, C₁₄H₁₂N₄O₆·C₃H₇NO, is a monoclinic polymorph of an already published structure [Baughman et al. (2004 ). Acta Cryst. C60, 103–106]. In the previously reported structure, the compound crystallized in the triclinic space group P $[\overline{1}]$ (Z = 2), whereas the structure reported here is monoclinic (P2₁/n, Z = 4). In both forms, two intramolecular hydrogen bonds result in the formation of a fairly planar hydrazone skeleton (r.m.s. deviations for all non-H atoms = 0.127 Å for the monoclinic from and 0.131 Å for the triclinic form) and each molecule is hydrogen bonded to one solvent molecule. The principal difference between the two forms lies in the different orientation of the two molecules. In the monoclinic form, the two molecules are almost coplanar [dihedral angle = 3.27 (2)°], whereas in the triclinic form the two molecules are almost mutulally perpendicular (dihedral angle = 85.3°).

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ); Gerdemann et al. (2002 ); Mallikarjun & Sangamesh (1997 ); Solomon & Lowery (1993 ). For the crystal structure of the triclinic polymorph, see: Baughman et al. (2004).

Experimental

Crystal data

C₁₄H₁₂N₄O₆·C₃H₇NO
M_r = 405.37
Monoclinic, P 2₁ /n
a = 6.7546 (6) Å
b = 20.9647 (18) Å
c = 13.3508 (13) Å
β = 99.772 (1)°
V = 1863.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.43 × 0.28 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.973
9407 measured reflections
3280 independent reflections
1642 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.142
S = 0.88
3280 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.547 (2)	146
O2—H2A⋯O7	0.82	1.81	2.611 (3)	164
N2—H2⋯O3	0.86	1.94	2.584 (3)	130

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050161/bt5693sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050161/bt5693Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050161/bt5693Isup3.cml

checkCIF report

Comment top

The Schiff bases containing the C═N bond have been receiving considerable attention for many years, primarily due to a wide range of biological properties including antifungal, antibacterial, herbicidal, antiproliferative, cytotoxic, anticonvulsant and anticancer activities (Khan et al., 2009; Gerdemann et al., 2002; Mallikarjun & Sangamesh, 1997; Solomon & Lowery, 1993). The title compound, (I), is a monoclinic polymorph of the previously reported crystal structure which crystallizes in the triclinic space group P1 (Baughman et al., 2004). The relative arrangement of the molecules observed in the current structure is different from that previously reported.

The molecular structure of (I) is shown in Fig. 1. It crystallizes in the space group P2₁/n, with four molecules in each unit cell. The azomethine double bond adopts an E configuration. The solvent molecule and Schiff base molecule are linked by O—H···N hydrogen bond. The planes of the solvent molecule and adjacent benzene ring linked by hydrogen bond are almost parallel. The dihedral angle is 0.209 (127). One N—H···O, one O—H···N and one O—H···O hydrogen bonds link the molecules, forming a two-dimensional network. Whereas in (II) the dihedral angle between the planes of the solvent molecule and adjacent benzene ring linked by O—H···N hydrogen bond is 86.619 (143). Besides above three kind of hydrogen bonds, intermolecular O5···O5ⁱ interaction (symmetry code i: 1 - x, 1 - y, 1 - z) link the molecules into a three-dimensional network.

Related literature top

For the biological activity of Schiff bases, see: Khan et al. (2009); Gerdemann et al. (2002); Mallikarjun & Sangamesh (1997); Solomon & Lowery (1993). For the crystal structure of the triclinic polymorph, see: Baughman et al. (2004).

Experimental top

The synthesis of title compound I was carried out by refluxing a mixture of 2,4-dihydroxyacetophenone (0.76 g, 5 mmol) and 2,4-dinitrophenylhydrazine (0.99 g, 5 mmol) with concentrated sulfuric acid (5 mL) in ethanol (20 mL) for 2 h. After cooling and filtration the crystalline product was collected, washed with hexane and dried to afford the title compound in 85% yield.

Structure description top

For the biological activity of Schiff bases, see: Khan et al. (2009); Gerdemann et al. (2002); Mallikarjun & Sangamesh (1997); Solomon & Lowery (1993). For the crystal structure of the triclinic polymorph, see: Baughman et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

4-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]ethyl}benzene-1,3-diol N,N-dimethylformamide monosolvate top

Crystal data top

C₁₄H₁₂N₄O₆·C₃H₇NO	F(000) = 848
M_r = 405.37	D_x = 1.445 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1386 reflections
a = 6.7546 (6) Å	θ = 3.0–21.9°
b = 20.9647 (18) Å	µ = 0.11 mm⁻¹
c = 13.3508 (13) Å	T = 298 K
β = 99.772 (1)°	Block, brown
V = 1863.2 (3) Å³	0.43 × 0.28 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	1642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
T_min = 0.953, T_max = 0.973	k = −17→24
9407 measured reflections	l = −15→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0687P)²] where P = (F_o² + 2F_c²)/3
3280 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₂N₄O₆·C₃H₇NO	V = 1863.2 (3) Å³
M_r = 405.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7546 (6) Å	µ = 0.11 mm⁻¹
b = 20.9647 (18) Å	T = 298 K
c = 13.3508 (13) Å	0.43 × 0.28 × 0.24 mm
β = 99.772 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3280 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1642 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.973	R_int = 0.058
9407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 0.88	Δρ_max = 0.25 e Å⁻³
3280 reflections	Δρ_min = −0.23 e Å⁻³
262 parameters

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	0.7588 (3)	0.58432 (9)	0.54589 (14)	0.0446 (5)
N2	0.7718 (3)	0.63470 (9)	0.61267 (15)	0.0479 (6)
H2	0.7949	0.6272	0.6769	0.058*
N3	0.7472 (4)	0.73692 (13)	0.75436 (18)	0.0709 (7)
N4	0.6738 (4)	0.88617 (12)	0.4785 (2)	0.0705 (7)
N5	0.8095 (4)	0.11311 (11)	0.45642 (17)	0.0620 (7)
O1	0.6979 (3)	0.54234 (8)	0.36429 (12)	0.0644 (6)
H1	0.7114	0.5692	0.4096	0.097*
O2	0.7018 (3)	0.32319 (8)	0.30681 (14)	0.0683 (6)
H2A	0.7141	0.2888	0.3365	0.102*
O3	0.7879 (4)	0.68408 (10)	0.79108 (14)	0.0790 (7)
O4	0.7151 (5)	0.78168 (11)	0.80637 (17)	0.1192 (11)
O5	0.6748 (4)	0.92791 (10)	0.5426 (2)	0.0961 (8)
O6	0.6526 (4)	0.89703 (10)	0.3875 (2)	0.0934 (8)
O7	0.7736 (4)	0.20700 (9)	0.37332 (18)	0.0801 (7)
C1	0.8138 (4)	0.51378 (13)	0.69559 (18)	0.0575 (7)
H1A	0.9127	0.5430	0.7293	0.086*
H1B	0.8615	0.4708	0.7074	0.086*
H1C	0.6909	0.5190	0.7217	0.086*
C2	0.7768 (4)	0.52710 (12)	0.58373 (18)	0.0422 (6)
C3	0.7571 (4)	0.47439 (11)	0.51209 (18)	0.0409 (6)
C4	0.7195 (4)	0.48320 (11)	0.40614 (19)	0.0454 (7)
C5	0.7022 (4)	0.43264 (12)	0.34011 (19)	0.0507 (7)
H5	0.6773	0.4401	0.2704	0.061*
C6	0.7211 (4)	0.37116 (12)	0.37582 (19)	0.0491 (7)
C7	0.7566 (4)	0.36059 (11)	0.47885 (19)	0.0507 (7)
H7	0.7688	0.3191	0.5039	0.061*
C8	0.7739 (4)	0.41082 (12)	0.54402 (19)	0.0488 (7)
H8	0.7982	0.4025	0.6134	0.059*
C9	0.7493 (4)	0.69475 (11)	0.58042 (19)	0.0448 (7)
C10	0.7384 (4)	0.74617 (12)	0.64741 (19)	0.0500 (7)
C11	0.7124 (4)	0.80809 (12)	0.6129 (2)	0.0557 (8)
H11	0.7038	0.8411	0.6585	0.067*
C12	0.6994 (4)	0.82073 (12)	0.5123 (2)	0.0540 (7)
C13	0.7114 (4)	0.77217 (13)	0.4441 (2)	0.0576 (8)
H13	0.7031	0.7814	0.3753	0.069*
C14	0.7354 (4)	0.71070 (12)	0.4767 (2)	0.0531 (7)
H14	0.7429	0.6785	0.4297	0.064*
C15	0.8017 (4)	0.17571 (14)	0.4520 (3)	0.0641 (8)
H15	0.8188	0.1979	0.5132	0.077*
C16	0.7826 (6)	0.07595 (15)	0.3644 (2)	0.0991 (12)
H16A	0.7287	0.1026	0.3078	0.149*
H16B	0.6913	0.0415	0.3697	0.149*
H16C	0.9097	0.0590	0.3543	0.149*
C17	0.8457 (5)	0.07943 (14)	0.5520 (2)	0.0817 (10)
H17A	0.8718	0.1096	0.6067	0.123*
H17B	0.9598	0.0519	0.5539	0.123*
H17C	0.7297	0.0544	0.5588	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0514 (14)	0.0378 (12)	0.0452 (12)	0.0018 (10)	0.0102 (11)	0.0009 (10)
N2	0.0622 (16)	0.0410 (13)	0.0408 (12)	0.0006 (11)	0.0091 (11)	−0.0022 (10)
N3	0.105 (2)	0.0534 (16)	0.0547 (16)	−0.0029 (15)	0.0131 (15)	−0.0086 (14)
N4	0.0691 (19)	0.0478 (16)	0.096 (2)	0.0019 (13)	0.0174 (17)	0.0128 (16)
N5	0.0782 (19)	0.0438 (14)	0.0644 (16)	0.0041 (13)	0.0128 (14)	−0.0072 (12)
O1	0.1061 (17)	0.0411 (11)	0.0449 (11)	0.0005 (10)	0.0097 (11)	0.0061 (9)
O2	0.1046 (17)	0.0450 (11)	0.0560 (12)	−0.0050 (11)	0.0153 (11)	−0.0062 (9)
O3	0.124 (2)	0.0610 (14)	0.0511 (13)	0.0039 (13)	0.0134 (12)	0.0014 (10)
O4	0.229 (3)	0.0657 (15)	0.0651 (16)	0.0233 (17)	0.0323 (18)	−0.0183 (12)
O5	0.126 (2)	0.0439 (12)	0.121 (2)	0.0026 (13)	0.0292 (17)	−0.0012 (13)
O6	0.124 (2)	0.0651 (15)	0.0915 (17)	0.0042 (13)	0.0190 (16)	0.0273 (14)
O7	0.0996 (19)	0.0539 (13)	0.0869 (17)	0.0088 (12)	0.0155 (14)	0.0077 (12)
C1	0.073 (2)	0.0522 (16)	0.0456 (16)	0.0012 (15)	0.0062 (14)	0.0007 (13)
C2	0.0428 (17)	0.0412 (15)	0.0430 (15)	0.0024 (12)	0.0088 (12)	0.0017 (12)
C3	0.0412 (16)	0.0381 (14)	0.0440 (15)	0.0007 (12)	0.0091 (12)	0.0033 (12)
C4	0.0507 (18)	0.0378 (15)	0.0485 (16)	−0.0007 (13)	0.0105 (13)	0.0052 (13)
C5	0.064 (2)	0.0439 (16)	0.0432 (16)	−0.0016 (14)	0.0078 (14)	0.0007 (13)
C6	0.0557 (19)	0.0429 (16)	0.0496 (17)	−0.0043 (13)	0.0115 (14)	−0.0054 (13)
C7	0.0612 (19)	0.0375 (15)	0.0540 (17)	0.0019 (13)	0.0119 (14)	0.0046 (13)
C8	0.0597 (19)	0.0451 (16)	0.0424 (15)	0.0030 (13)	0.0112 (13)	0.0067 (13)
C9	0.0456 (17)	0.0384 (15)	0.0509 (16)	−0.0031 (12)	0.0092 (13)	0.0007 (13)
C10	0.0584 (19)	0.0451 (16)	0.0466 (16)	−0.0010 (13)	0.0088 (13)	−0.0037 (13)
C11	0.059 (2)	0.0449 (17)	0.0644 (19)	−0.0024 (14)	0.0144 (15)	−0.0097 (14)
C12	0.0520 (19)	0.0393 (16)	0.071 (2)	0.0034 (13)	0.0125 (15)	0.0059 (14)
C13	0.064 (2)	0.0564 (19)	0.0527 (17)	−0.0011 (15)	0.0102 (15)	0.0083 (14)
C14	0.065 (2)	0.0456 (16)	0.0485 (17)	−0.0003 (14)	0.0101 (14)	−0.0017 (13)
C15	0.064 (2)	0.050 (2)	0.080 (2)	0.0019 (16)	0.0179 (18)	−0.0065 (17)
C16	0.143 (4)	0.067 (2)	0.080 (2)	0.010 (2)	0.001 (2)	−0.0239 (19)
C17	0.097 (3)	0.065 (2)	0.086 (2)	0.0105 (19)	0.020 (2)	0.0072 (18)

Geometric parameters (Å, º) top

N1—C2	1.299 (3)	C3—C4	1.406 (3)
N1—N2	1.375 (2)	C4—C5	1.371 (3)
N2—C9	1.331 (3)	C5—C6	1.373 (3)
N2—H2	0.8600	C5—H5	0.9300
N3—O4	1.209 (3)	C6—C7	1.374 (3)
N3—O3	1.224 (3)	C7—C8	1.358 (3)
N3—C10	1.432 (3)	C7—H7	0.9300
N4—O6	1.220 (3)	C8—H8	0.9300
N4—O5	1.223 (3)	C9—C10	1.411 (3)
N4—C12	1.445 (3)	C9—C14	1.412 (3)
N5—C15	1.314 (3)	C10—C11	1.379 (3)
N5—C17	1.442 (3)	C11—C12	1.357 (4)
N5—C16	1.440 (3)	C11—H11	0.9300
O1—C4	1.358 (3)	C12—C13	1.378 (4)
O1—H1	0.8200	C13—C14	1.361 (3)
O2—C6	1.355 (3)	C13—H13	0.9300
O2—H2A	0.8200	C14—H14	0.9300
O7—C15	1.226 (3)	C15—H15	0.9300
C1—C2	1.498 (3)	C16—H16A	0.9600
C1—H1A	0.9600	C16—H16B	0.9600
C1—H1B	0.9600	C16—H16C	0.9600
C1—H1C	0.9600	C17—H17A	0.9600
C2—C3	1.453 (3)	C17—H17B	0.9600
C3—C8	1.398 (3)	C17—H17C	0.9600

C2—N1—N2	117.74 (19)	C6—C7—H7	120.1
C9—N2—N1	121.7 (2)	C7—C8—C3	123.4 (2)
C9—N2—H2	119.1	C7—C8—H8	118.3
N1—N2—H2	119.1	C3—C8—H8	118.3
O4—N3—O3	121.5 (2)	N2—C9—C10	122.2 (2)
O4—N3—C10	119.1 (3)	N2—C9—C14	121.8 (2)
O3—N3—C10	119.4 (2)	C10—C9—C14	116.0 (2)
O6—N4—O5	123.3 (3)	C11—C10—C9	121.7 (2)
O6—N4—C12	118.4 (3)	C11—C10—N3	116.2 (2)
O5—N4—C12	118.4 (3)	C9—C10—N3	122.1 (2)
C15—N5—C17	121.9 (3)	C12—C11—C10	119.8 (3)
C15—N5—C16	120.3 (3)	C12—C11—H11	120.1
C17—N5—C16	117.9 (2)	C10—C11—H11	120.1
C4—O1—H1	109.5	C11—C12—C13	120.6 (2)
C6—O2—H2A	109.5	C11—C12—N4	118.6 (3)
C2—C1—H1A	109.5	C13—C12—N4	120.8 (3)
C2—C1—H1B	109.5	C14—C13—C12	120.3 (3)
H1A—C1—H1B	109.5	C14—C13—H13	119.8
C2—C1—H1C	109.5	C12—C13—H13	119.8
H1A—C1—H1C	109.5	C13—C14—C9	121.5 (2)
H1B—C1—H1C	109.5	C13—C14—H14	119.2
N1—C2—C3	117.0 (2)	C9—C14—H14	119.2
N1—C2—C1	123.3 (2)	O7—C15—N5	124.9 (3)
C3—C2—C1	119.7 (2)	O7—C15—H15	117.6
C8—C3—C4	115.0 (2)	N5—C15—H15	117.6
C8—C3—C2	122.1 (2)	N5—C16—H16A	109.5
C4—C3—C2	122.9 (2)	N5—C16—H16B	109.5
O1—C4—C5	116.7 (2)	H16A—C16—H16B	109.5
O1—C4—C3	121.5 (2)	N5—C16—H16C	109.5
C5—C4—C3	121.8 (2)	H16A—C16—H16C	109.5
C4—C5—C6	120.7 (2)	H16B—C16—H16C	109.5
C4—C5—H5	119.7	N5—C17—H17A	109.5
C6—C5—H5	119.7	N5—C17—H17B	109.5
O2—C6—C5	117.9 (2)	H17A—C17—H17B	109.5
O2—C6—C7	122.8 (2)	N5—C17—H17C	109.5
C5—C6—C7	119.3 (2)	H17A—C17—H17C	109.5
C8—C7—C6	119.9 (2)	H17B—C17—H17C	109.5
C8—C7—H7	120.1

C2—N1—N2—C9	−178.1 (2)	C14—C9—C10—C11	1.0 (4)
N2—N1—C2—C3	178.3 (2)	N2—C9—C10—N3	−1.1 (4)
N2—N1—C2—C1	−1.0 (4)	C14—C9—C10—N3	179.0 (3)
N1—C2—C3—C8	179.9 (2)	O4—N3—C10—C11	6.1 (4)
C1—C2—C3—C8	−0.8 (4)	O3—N3—C10—C11	−173.5 (3)
N1—C2—C3—C4	−0.2 (4)	O4—N3—C10—C9	−172.0 (3)
C1—C2—C3—C4	179.1 (2)	O3—N3—C10—C9	8.4 (4)
C8—C3—C4—O1	179.4 (2)	C9—C10—C11—C12	−0.9 (4)
C2—C3—C4—O1	−0.5 (4)	N3—C10—C11—C12	−179.0 (3)
C8—C3—C4—C5	−0.3 (4)	C10—C11—C12—C13	0.2 (4)
C2—C3—C4—C5	179.8 (2)	C10—C11—C12—N4	−179.5 (3)
O1—C4—C5—C6	−179.8 (2)	O6—N4—C12—C11	−176.6 (3)
C3—C4—C5—C6	0.0 (4)	O5—N4—C12—C11	3.5 (4)
C4—C5—C6—O2	179.8 (2)	O6—N4—C12—C13	3.8 (4)
C4—C5—C6—C7	0.4 (4)	O5—N4—C12—C13	−176.1 (3)
O2—C6—C7—C8	−179.8 (2)	C11—C12—C13—C14	0.4 (4)
C5—C6—C7—C8	−0.5 (4)	N4—C12—C13—C14	−180.0 (3)
C6—C7—C8—C3	0.1 (4)	C12—C13—C14—C9	−0.2 (4)
C4—C3—C8—C7	0.3 (4)	N2—C9—C14—C13	179.6 (2)
C2—C3—C8—C7	−179.8 (2)	C10—C9—C14—C13	−0.5 (4)
N1—N2—C9—C10	172.3 (2)	C17—N5—C15—O7	179.2 (3)
N1—N2—C9—C14	−7.8 (4)	C16—N5—C15—O7	−0.5 (5)
N2—C9—C10—C11	−179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.547 (2)	146
O2—H2A···O7	0.82	1.81	2.611 (3)	164
N2—H2···O3	0.86	1.94	2.584 (3)	130

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₄O₆·C₃H₇NO
M_r	405.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.7546 (6), 20.9647 (18), 13.3508 (13)
β (°)	99.772 (1)
V (Å³)	1863.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.43 × 0.28 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	9407, 3280, 1642
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.142, 0.88
No. of reflections	3280
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.820	1.823	2.547 (2)	146
O2—H2A···O7	0.820	1.812	2.611 (3)	164
N2—H2···O3	0.860	1.944	2.584 (3)	130

Acknowledgements

This work was carried out under the sponsorship of the project of ShanXi Scientific Technology (20110321044).

References

Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103–o106. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183–191. Web of Science CrossRef PubMed CAS Google Scholar
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801. Web of Science CrossRef PubMed CAS Google Scholar
Mallikarjun, S. Y. & Sangamesh, A. P. (1997). Transition Met. Chem. 22, 220–224. Google Scholar
Sheldrick, G. M. (1996). SADABS . University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solomon, E. I. & Lowery, M. D. (1993). Science, 259, 1575–1581. CrossRef CAS PubMed Web of Science Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

A monoclinic polymorph with Z = 4 of (E)-2,4-dihy­dr­oxy­aceto­phenone 2,4-di­nitro­phenyl­hydrazone N,N-di­methyl­formamide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

A monoclinic polymorph with Z = 4 of (E)-2,4-dihydroxyacetophenone 2,4-dinitrophenylhydrazone N,N-dimethylformamide monosolvate