(Z)-3-[2-(2,4-Di-nitro-phen-yl)hydrazin-1-yl-idene]isobenzo-furan-1(3H)-one di-chloro-methane hemisolvate.

In the title compound, 2C14H8N4O6·CH2Cl2, the di-chloro-methane solvent mol-ecule resides on a crystallographic twofold axis. The mean plane of the phthaliso-imide ring is oriented at a dihedral angle of 32.93 (12)° with respect to the nitro-substituted benzene ring. An intra-molecular N-H⋯O hydrogen bond occurs. The crystal packing features a short Cl⋯O halogen-bond inter-action [3.093 (3) Å].

Related literature

For a general background, see: Kaufmann (1927 ▶); Maekawa & Nanya (1959 ▶). For the preparation of hydrazone derivatives of phthalic anhydride, see: Chen et al. (1990 ▶). For halogen bond inter­actions, see: Gonnade et al. (2008 ▶); Metrangalo & Resnati (2007 ▶); Pedireddi et al. (1992 ▶). For a related structure, see: Guirado et al. (1997 ▶).

Experimental

Crystal data

2C14H8N4O6·CH2Cl2

M = 741.41

Monoclinic,

a = 14.0834 (11) Å

b = 8.2605 (6) Å

c = 26.561 (2) Å

β = 93.816 (7)°

V = 3083.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 297 K

0.40 × 0.40 × 0.15 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.824, T max = 1.000

20814 measured reflections

3832 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.141

S = 1.03

3832 reflections

234 parameters

Only H-atom displacement parameters refined

Δρmax = 0.44 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814004929/fj2664sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004929/fj2664Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004929/fj2664Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814004929/fj2664Isup4.cml

CCDC reference: 989735

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C14H8N4O6·CH2Cl2	F(000) = 1512
Mr = 741.41	Dx = 1.597 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.0834 (11) Å	Cell parameters from 3399 reflections
b = 8.2605 (6) Å	θ = 3.0–29.2°
c = 26.561 (2) Å	µ = 0.29 mm−1
β = 93.816 (7)°	T = 297 K
V = 3083.2 (3) Å3	Rect. prism, clear yellow–red
Z = 4	0.4 × 0.4 × 0.15 mm

Agilent Xcalibur Sapphire3 diffractometer	3832 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 15.9853 pixels mm-1	θmax = 29.3°, θmin = 3.0°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→10
Tmin = 0.824, Tmax = 1.000	l = −35→36
20814 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057	Only H-atom displacement parameters refined
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.053P)2 + 3.247P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3832 reflections	Δρmax = 0.44 e Å−3
234 parameters	Δρmin = −0.35 e Å−3
0 restraints

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.39898 (6)	0.54376 (10)	0.73756 (3)	0.0797 (3)
O2	0.41801 (11)	0.47047 (18)	0.54833 (5)	0.0411 (4)
O3	0.30079 (13)	0.1587 (2)	0.45274 (6)	0.0566 (5)
O4	0.48996 (13)	0.4056 (2)	0.62423 (6)	0.0562 (5)
O5	0.24791 (13)	0.0449 (2)	0.38349 (7)	0.0554 (5)
N6	0.33004 (14)	0.4709 (2)	0.45706 (7)	0.0407 (4)
H6	0.3319 (18)	0.386 (3)	0.4723 (9)	0.049*
N7	0.26939 (13)	0.1660 (2)	0.40803 (7)	0.0408 (4)
N8	0.16035 (16)	0.4760 (3)	0.26002 (7)	0.0529 (5)
N9	0.35397 (13)	0.6171 (2)	0.47867 (6)	0.0403 (4)
C10	0.21556 (15)	0.3263 (3)	0.33550 (8)	0.0381 (5)
H10	0.1961	0.2307	0.3195	0.046*
C11	0.42937 (14)	0.7496 (3)	0.55314 (8)	0.0357 (5)
C12	0.39564 (15)	0.6131 (3)	0.52246 (8)	0.0371 (5)
C13	0.47111 (15)	0.6872 (3)	0.59783 (8)	0.0377 (5)
C14	0.46430 (15)	0.5103 (3)	0.59583 (8)	0.0400 (5)
O15	0.1569 (2)	0.6044 (3)	0.23776 (8)	0.0904 (8)
O16	0.13589 (19)	0.3503 (3)	0.23967 (7)	0.0891 (8)
C17	0.28732 (14)	0.4683 (3)	0.40931 (7)	0.0355 (5)
C18	0.25776 (14)	0.3240 (3)	0.38441 (8)	0.0351 (5)
C19	0.20337 (15)	0.4720 (3)	0.31152 (8)	0.0396 (5)
C20	0.42629 (17)	0.9146 (3)	0.54405 (9)	0.0443 (5)
H20	0.3976	0.9565	0.5143	0.053*
C21	0.46757 (18)	1.0142 (3)	0.58095 (10)	0.0508 (6)
H21	0.4676	1.1255	0.5757	0.061*
C22	0.23198 (16)	0.6165 (3)	0.33451 (8)	0.0440 (5)
H22	0.2230	0.7141	0.3174	0.053*
C23	0.50939 (17)	0.9519 (3)	0.62607 (9)	0.0495 (6)
H23	0.5361	1.0227	0.6503	0.059*
C24	0.27340 (16)	0.6143 (3)	0.38250 (8)	0.0410 (5)
H24	0.2928	0.7112	0.3978	0.049*
C25	0.51179 (16)	0.7874 (3)	0.63543 (9)	0.0449 (6)
H25	0.5393	0.7456	0.6655	0.054*
C26	0.5000	0.4238 (5)	0.7500	0.0587 (10)
H26	0.4913	0.3631	0.7795	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.0687 (5)	0.0757 (5)	0.0948 (6)	0.0155 (4)	0.0049 (4)	0.0027 (4)
O2	0.0502 (9)	0.0379 (8)	0.0340 (8)	0.0005 (7)	−0.0059 (7)	−0.0030 (7)
O3	0.0822 (13)	0.0478 (10)	0.0378 (9)	0.0001 (9)	−0.0120 (8)	0.0103 (8)
O4	0.0750 (12)	0.0465 (10)	0.0451 (10)	0.0060 (9)	−0.0122 (8)	0.0055 (8)
O5	0.0755 (12)	0.0371 (9)	0.0523 (10)	−0.0031 (8)	−0.0053 (9)	−0.0018 (8)
N6	0.0515 (11)	0.0388 (11)	0.0306 (10)	−0.0002 (9)	−0.0056 (8)	−0.0004 (8)
N7	0.0447 (10)	0.0401 (11)	0.0371 (10)	0.0008 (8)	−0.0003 (8)	0.0028 (8)
N8	0.0681 (14)	0.0512 (13)	0.0371 (11)	0.0025 (11)	−0.0126 (10)	0.0015 (10)
N9	0.0465 (10)	0.0418 (11)	0.0321 (9)	0.0003 (8)	−0.0013 (8)	−0.0045 (8)
C10	0.0406 (11)	0.0419 (12)	0.0311 (11)	0.0021 (10)	−0.0026 (9)	−0.0042 (9)
C11	0.0364 (10)	0.0406 (12)	0.0300 (10)	0.0003 (9)	0.0015 (8)	−0.0046 (9)
C12	0.0407 (11)	0.0391 (12)	0.0312 (11)	0.0045 (9)	−0.0001 (9)	−0.0010 (9)
C13	0.0372 (11)	0.0420 (12)	0.0339 (11)	0.0013 (9)	0.0011 (9)	−0.0034 (9)
C14	0.0418 (12)	0.0427 (13)	0.0348 (11)	0.0023 (10)	−0.0019 (9)	−0.0021 (10)
O15	0.151 (2)	0.0621 (13)	0.0527 (12)	0.0099 (14)	−0.0355 (13)	0.0106 (10)
O16	0.142 (2)	0.0669 (14)	0.0526 (12)	−0.0249 (14)	−0.0391 (13)	0.0023 (11)
C17	0.0340 (10)	0.0435 (12)	0.0287 (10)	0.0018 (9)	−0.0002 (8)	−0.0007 (9)
C18	0.0366 (10)	0.0362 (11)	0.0325 (11)	0.0033 (9)	0.0021 (8)	0.0006 (9)
C19	0.0421 (12)	0.0476 (13)	0.0282 (11)	0.0032 (10)	−0.0045 (9)	−0.0002 (10)
C20	0.0512 (13)	0.0395 (13)	0.0422 (12)	0.0028 (10)	0.0029 (10)	0.0016 (10)
C21	0.0580 (15)	0.0380 (13)	0.0570 (15)	−0.0044 (11)	0.0085 (12)	−0.0060 (11)
C22	0.0537 (14)	0.0413 (13)	0.0360 (12)	0.0056 (11)	−0.0032 (10)	0.0068 (10)
C23	0.0505 (14)	0.0505 (15)	0.0475 (14)	−0.0073 (11)	0.0028 (11)	−0.0169 (12)
C24	0.0489 (13)	0.0360 (12)	0.0374 (12)	0.0006 (10)	−0.0028 (10)	−0.0018 (9)
C25	0.0441 (12)	0.0541 (15)	0.0356 (12)	−0.0018 (11)	−0.0033 (9)	−0.0085 (10)
C26	0.070 (2)	0.052 (2)	0.053 (2)	0.000	−0.0091 (18)	0.000

Cl1—C26	1.747 (2)	C11—C20	1.385 (3)
O2—C12	1.389 (3)	C13—C14	1.466 (3)
O2—C14	1.419 (3)	C13—C25	1.391 (3)
O3—N7	1.241 (2)	C17—C18	1.413 (3)
O4—C14	1.188 (3)	C17—C24	1.407 (3)
O5—N7	1.221 (2)	C19—C22	1.389 (3)
N6—H6	0.81 (3)	C20—H20	0.9300
N6—N9	1.370 (3)	C20—C21	1.378 (3)
N6—C17	1.367 (3)	C21—H21	0.9300
N7—C18	1.453 (3)	C21—C23	1.398 (4)
N8—O15	1.214 (3)	C22—H22	0.9300
N8—O16	1.210 (3)	C22—C24	1.366 (3)
N8—C19	1.459 (3)	C23—H23	0.9300
N9—C12	1.268 (3)	C23—C25	1.382 (3)
C10—H10	0.9300	C24—H24	0.9300
C10—C18	1.392 (3)	C25—H25	0.9300
C10—C19	1.367 (3)	C26—Cl1i	1.747 (2)
C11—C12	1.453 (3)	C26—H26	0.9440
C11—C13	1.388 (3)
C12—O2—C14	108.59 (16)	C24—C17—C18	117.35 (18)
N9—N6—H6	123.9 (18)	C10—C18—N7	116.37 (19)
C17—N6—H6	116.5 (18)	C10—C18—C17	121.29 (19)
C17—N6—N9	118.88 (18)	C17—C18—N7	122.34 (18)
O3—N7—C18	118.66 (18)	C10—C19—N8	119.2 (2)
O5—N7—O3	122.09 (19)	C10—C19—C22	121.89 (19)
O5—N7—C18	119.25 (17)	C22—C19—N8	118.9 (2)
O15—N8—C19	118.5 (2)	C11—C20—H20	121.4
O16—N8—O15	122.1 (2)	C21—C20—C11	117.2 (2)
O16—N8—C19	119.2 (2)	C21—C20—H20	121.4
C12—N9—N6	116.54 (18)	C20—C21—H21	119.2
C18—C10—H10	120.7	C20—C21—C23	121.6 (2)
C19—C10—H10	120.7	C23—C21—H21	119.2
C19—C10—C18	118.7 (2)	C19—C22—H22	120.3
C13—C11—C12	107.21 (19)	C24—C22—C19	119.5 (2)
C20—C11—C12	131.4 (2)	C24—C22—H22	120.3
C20—C11—C13	121.4 (2)	C21—C23—H23	119.3
O2—C12—C11	109.01 (17)	C25—C23—C21	121.4 (2)
N9—C12—O2	123.53 (19)	C25—C23—H23	119.3
N9—C12—C11	127.5 (2)	C17—C24—H24	119.3
C11—C13—C14	108.41 (19)	C22—C24—C17	121.3 (2)
C11—C13—C25	121.6 (2)	C22—C24—H24	119.3
C25—C13—C14	130.0 (2)	C13—C25—H25	121.6
O2—C14—C13	106.77 (18)	C23—C25—C13	116.9 (2)
O4—C14—O2	119.9 (2)	C23—C25—H25	121.6
O4—C14—C13	133.3 (2)	Cl1—C26—Cl1i	110.9 (2)
N6—C17—C18	123.03 (19)	Cl1—C26—H26	108.0
N6—C17—C24	119.6 (2)	Cl1i—C26—H26	107.0
O3—N7—C18—C10	−175.26 (19)	C14—O2—C12—N9	179.8 (2)
O3—N7—C18—C17	4.7 (3)	C14—O2—C12—C11	1.0 (2)
O5—N7—C18—C10	4.6 (3)	C14—C13—C25—C23	178.5 (2)
O5—N7—C18—C17	−175.45 (19)	O15—N8—C19—C10	−174.2 (2)
N6—N9—C12—O2	0.6 (3)	O15—N8—C19—C22	5.0 (4)
N6—N9—C12—C11	179.12 (19)	O16—N8—C19—C10	0.4 (4)
N6—C17—C18—N7	0.8 (3)	O16—N8—C19—C22	179.5 (2)
N6—C17—C18—C10	−179.2 (2)	C17—N6—N9—C12	−178.2 (2)
N6—C17—C24—C22	179.2 (2)	C18—C10—C19—N8	179.22 (19)
N8—C19—C22—C24	−179.2 (2)	C18—C10—C19—C22	0.1 (3)
N9—N6—C17—C18	−178.27 (18)	C18—C17—C24—C22	0.7 (3)
N9—N6—C17—C24	3.3 (3)	C19—C10—C18—N7	−179.73 (18)
C10—C19—C22—C24	−0.1 (3)	C19—C10—C18—C17	0.3 (3)
C11—C13—C14—O2	0.5 (2)	C19—C22—C24—C17	−0.3 (3)
C11—C13—C14—O4	179.2 (3)	C20—C11—C12—O2	178.5 (2)
C11—C13—C25—C23	−0.5 (3)	C20—C11—C12—N9	−0.1 (4)
C11—C20—C21—C23	−1.1 (3)	C20—C11—C13—C14	−179.2 (2)
C12—O2—C14—O4	−179.9 (2)	C20—C11—C13—C25	−0.1 (3)
C12—O2—C14—C13	−1.0 (2)	C20—C21—C23—C25	0.5 (4)
C12—C11—C13—C14	0.1 (2)	C21—C23—C25—C13	0.3 (3)
C12—C11—C13—C25	179.23 (19)	C24—C17—C18—N7	179.32 (19)
C12—C11—C20—C21	−178.3 (2)	C24—C17—C18—C10	−0.7 (3)
C13—C11—C12—O2	−0.7 (2)	C25—C13—C14—O2	−178.5 (2)
C13—C11—C12—N9	−179.4 (2)	C25—C13—C14—O4	0.2 (4)
C13—C11—C20—C21	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O3	0.81 (3)	1.99 (3)	2.613 (3)	134 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O3	0.81 (3)	1.99 (3)	2.613 (3)	134 (2)