2-(1,3-Dioxoisoindolin-2-yl)acetic acid-N'-[(E)-2-meth-oxy-benzyl-idene]pyridine-4-carbohydrazide (1/1).

In the title 1:1 cocrystal, C(10)H(7)NO(4)·C(14)H(13)N(3)O(2), mol-ecules are linked by inter-molecular C-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds, forming a three-dimensional network. In addition, π-π stacking inter-actions [with centroid-centroid distances of 3.5723 (19) and 3.6158 (18) Å] are observed.

Related literature

For the use of co-crystals in drug design and delivery, see: Vishweshwar et al. (2009 ▶); Peterson et al. (2006 ▶); McNamara et al. (2006 ▶). For anti-tuberculosis drugs containing the isoniazid core structure, see: Bijev (2006 ▶); Imramovský et al. (2007 ▶); Maccari et al. (2005 ▶); Schultheiss & Newman (2009 ▶); Shindikar & Viswanathan (2005 ▶); Sinha et al. (2005 ▶); Sriram et al. (2006 ▶).

Experimental

Crystal data

C10H7NO4·C14H13N3O2

M = 460.44

Monoclinic,

a = 7.0747 (10) Å

b = 43.511 (6) Å

c = 7.5477 (9) Å

β = 110.015 (5)°

V = 2183.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.980

19892 measured reflections

4304 independent reflections

2345 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.02

4304 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031388/qm2075sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031388/qm2075Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031388/qm2075Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H7NO4·C14H13N3O2	F(000) = 960
Mr = 460.44	Dx = 1.401 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 410 reflections
a = 7.0747 (10) Å	θ = 2.8–18.3°
b = 43.511 (6) Å	µ = 0.10 mm−1
c = 7.5477 (9) Å	T = 296 K
β = 110.015 (5)°	Prism, white
V = 2183.1 (5) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4304 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.970, Tmax = 0.980	k = −53→53
19892 measured reflections	l = −9→6

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.2903P] where P = (Fo2 + 2Fc2)/3
4304 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O5	0.9659 (3)	0.13677 (4)	0.9365 (3)	0.0713 (9)
O6	0.7705 (3)	0.28342 (4)	0.8630 (2)	0.0491 (7)
N2	0.9227 (3)	0.22710 (5)	0.8728 (3)	0.0448 (8)
N3	0.9636 (3)	0.24511 (5)	1.0332 (3)	0.0431 (8)
N4	0.9687 (3)	0.32666 (5)	1.5100 (3)	0.0475 (9)
C11	0.9448 (4)	0.17874 (6)	0.7399 (4)	0.0426 (10)
C12	0.9519 (4)	0.14724 (6)	0.7626 (4)	0.0527 (11)
C13	0.9412 (5)	0.12788 (7)	0.6119 (5)	0.0733 (14)
C14	0.9201 (5)	0.14100 (10)	0.4399 (5)	0.0838 (16)
C15	0.9080 (5)	0.17224 (9)	0.4141 (5)	0.0780 (16)
C16	0.9193 (4)	0.19068 (7)	0.5638 (4)	0.0574 (11)
C17	0.9700 (4)	0.19899 (6)	0.9011 (4)	0.0425 (9)
C18	0.8817 (4)	0.27317 (6)	1.0142 (4)	0.0383 (9)
C19	0.9250 (3)	0.29134 (5)	1.1918 (3)	0.0345 (8)
C20	0.9321 (4)	0.32285 (6)	1.1838 (4)	0.0425 (9)
C21	0.9562 (4)	0.33942 (6)	1.3457 (4)	0.0478 (10)
C22	0.9617 (4)	0.29627 (6)	1.5154 (4)	0.0474 (10)
C23	0.9432 (4)	0.27773 (6)	1.3624 (3)	0.0432 (9)
C24	0.9578 (6)	0.10465 (7)	0.9630 (5)	0.0989 (18)
O1	0.1383 (4)	0.04421 (5)	0.1887 (3)	0.0801 (9)
O2	0.8106 (4)	0.05255 (5)	0.4959 (3)	0.0820 (9)
O3	0.4269 (3)	0.13691 (4)	0.2806 (3)	0.0563 (7)
O4	0.5019 (4)	0.09977 (4)	0.1147 (3)	0.0768 (9)
N1	0.4681 (4)	0.05545 (5)	0.3577 (3)	0.0530 (9)
C1	0.3116 (5)	0.03656 (7)	0.2495 (4)	0.0554 (11)
C2	0.4075 (5)	0.00722 (6)	0.2291 (4)	0.0524 (10)
C3	0.3233 (5)	−0.01899 (7)	0.1349 (4)	0.0665 (14)
C4	0.4514 (7)	−0.04291 (7)	0.1340 (4)	0.0748 (14)
C5	0.6539 (7)	−0.04044 (7)	0.2267 (5)	0.0771 (14)
C6	0.7384 (6)	−0.01406 (7)	0.3214 (4)	0.0711 (14)
C7	0.6119 (5)	0.00973 (6)	0.3213 (4)	0.0528 (10)
C8	0.6528 (5)	0.04091 (7)	0.4045 (4)	0.0562 (11)
C9	0.4417 (5)	0.08717 (6)	0.3977 (4)	0.0571 (10)
C10	0.4610 (4)	0.10833 (6)	0.2468 (4)	0.0495 (10)
H3B	1.03930	0.23840	1.14160	0.0520*
H13	0.94820	0.10670	0.62710	0.0880*
H14	0.91390	0.12830	0.33880	0.1000*
H15	0.89240	0.18070	0.29680	0.0940*
H16	0.90950	0.21190	0.54670	0.0690*
H17	1.02040	0.19130	1.02330	0.0510*
H20	0.92090	0.33280	1.07150	0.0510*
H21	0.96430	0.36070	1.34000	0.0570*
H22	0.96960	0.28690	1.62860	0.0570*
H23	0.94310	0.25640	1.37370	0.0520*
H24A	0.83290	0.09670	0.87840	0.1490*
H24B	0.96730	0.10060	1.09080	0.1490*
H24C	1.06770	0.09490	0.93790	0.1490*
H3	0.18520	−0.02070	0.07370	0.0800*
H3A	0.44340	0.14810	0.19960	0.0840*
H4	0.39910	−0.06090	0.06940	0.0900*
H5	0.73670	−0.05700	0.22570	0.0920*
H6	0.87640	−0.01250	0.38320	0.0850*
H9A	0.54170	0.09270	0.51780	0.0680*
H9B	0.30990	0.08980	0.40850	0.0680*

	U11	U22	U33	U12	U13	U23
O5	0.0945 (17)	0.0458 (13)	0.0698 (15)	0.0059 (11)	0.0233 (12)	0.0036 (11)
O6	0.0610 (13)	0.0456 (11)	0.0326 (10)	0.0085 (9)	0.0054 (9)	0.0006 (8)
N2	0.0474 (14)	0.0426 (14)	0.0398 (13)	0.0021 (11)	0.0089 (10)	−0.0081 (10)
N3	0.0519 (14)	0.0403 (13)	0.0301 (12)	0.0075 (11)	0.0050 (10)	−0.0024 (10)
N4	0.0560 (16)	0.0456 (15)	0.0419 (14)	−0.0016 (11)	0.0179 (11)	−0.0047 (11)
C11	0.0352 (16)	0.0470 (17)	0.0452 (17)	−0.0030 (12)	0.0132 (12)	−0.0063 (13)
C12	0.0480 (19)	0.0502 (19)	0.0577 (19)	−0.0030 (14)	0.0154 (15)	−0.0086 (15)
C13	0.064 (2)	0.061 (2)	0.092 (3)	−0.0124 (17)	0.0228 (19)	−0.034 (2)
C14	0.079 (3)	0.108 (3)	0.068 (2)	−0.026 (2)	0.030 (2)	−0.044 (2)
C15	0.079 (3)	0.107 (3)	0.053 (2)	−0.030 (2)	0.0289 (18)	−0.019 (2)
C16	0.059 (2)	0.071 (2)	0.0436 (18)	−0.0141 (15)	0.0193 (15)	−0.0080 (15)
C17	0.0410 (16)	0.0442 (17)	0.0432 (15)	0.0010 (13)	0.0157 (12)	−0.0013 (13)
C18	0.0391 (16)	0.0390 (16)	0.0369 (15)	−0.0013 (12)	0.0131 (12)	0.0007 (12)
C19	0.0288 (14)	0.0390 (15)	0.0340 (14)	0.0002 (11)	0.0084 (11)	0.0010 (11)
C20	0.0460 (17)	0.0449 (17)	0.0360 (15)	−0.0030 (13)	0.0131 (12)	0.0019 (12)
C21	0.0545 (19)	0.0391 (16)	0.0489 (18)	−0.0064 (13)	0.0166 (14)	−0.0018 (14)
C22	0.0557 (19)	0.0493 (18)	0.0380 (15)	0.0031 (14)	0.0170 (13)	0.0041 (13)
C23	0.0527 (18)	0.0374 (15)	0.0407 (16)	0.0046 (13)	0.0177 (13)	0.0039 (12)
C24	0.125 (4)	0.047 (2)	0.114 (3)	0.001 (2)	0.027 (3)	0.014 (2)
O1	0.0718 (17)	0.0643 (15)	0.0895 (16)	0.0049 (13)	0.0088 (13)	0.0052 (12)
O2	0.0728 (17)	0.0660 (15)	0.0948 (17)	−0.0089 (13)	0.0128 (14)	−0.0199 (13)
O3	0.0881 (15)	0.0373 (11)	0.0495 (12)	0.0022 (10)	0.0312 (11)	0.0029 (9)
O4	0.136 (2)	0.0485 (13)	0.0652 (14)	0.0040 (12)	0.0592 (15)	−0.0054 (11)
N1	0.0680 (18)	0.0366 (13)	0.0507 (14)	−0.0013 (12)	0.0155 (13)	0.0014 (11)
C1	0.069 (2)	0.0473 (18)	0.0458 (17)	−0.0029 (17)	0.0143 (16)	0.0084 (14)
C2	0.080 (2)	0.0372 (17)	0.0402 (16)	−0.0030 (15)	0.0207 (16)	0.0047 (13)
C3	0.094 (3)	0.050 (2)	0.0545 (19)	−0.0154 (19)	0.0243 (18)	−0.0047 (15)
C4	0.127 (3)	0.043 (2)	0.062 (2)	−0.014 (2)	0.042 (2)	−0.0098 (16)
C5	0.119 (3)	0.048 (2)	0.075 (2)	0.013 (2)	0.047 (2)	0.0021 (18)
C6	0.087 (3)	0.055 (2)	0.071 (2)	0.0114 (19)	0.0266 (19)	−0.0008 (17)
C7	0.072 (2)	0.0431 (18)	0.0423 (16)	−0.0014 (15)	0.0181 (16)	0.0025 (13)
C8	0.071 (2)	0.0447 (18)	0.0505 (18)	−0.0034 (17)	0.0178 (17)	−0.0006 (14)
C9	0.083 (2)	0.0366 (16)	0.0546 (18)	−0.0009 (15)	0.0275 (16)	0.0006 (13)
C10	0.063 (2)	0.0380 (17)	0.0460 (17)	−0.0006 (13)	0.0168 (15)	−0.0031 (14)

O5—C12	1.361 (4)	C22—C23	1.378 (4)
O5—C24	1.416 (4)	C13—H13	0.9300
O6—C18	1.227 (3)	C14—H14	0.9300
O1—C1	1.200 (5)	C15—H15	0.9300
O2—C8	1.205 (4)	C16—H16	0.9300
O3—C10	1.308 (3)	C17—H17	0.9300
O4—C10	1.189 (4)	C20—H20	0.9300
O3—H3A	0.8200	C21—H21	0.9300
N2—N3	1.387 (3)	C22—H22	0.9300
N2—C17	1.267 (3)	C23—H23	0.9300
N3—C18	1.338 (3)	C24—H24A	0.9600
N4—C21	1.334 (4)	C24—H24B	0.9600
N4—C22	1.324 (3)	C24—H24C	0.9600
N3—H3B	0.8600	C1—C2	1.478 (4)
N1—C9	1.439 (3)	C2—C3	1.368 (4)
N1—C8	1.384 (4)	C2—C7	1.378 (5)
N1—C1	1.396 (4)	C3—C4	1.382 (5)
C11—C17	1.463 (4)	C4—C5	1.367 (7)
C11—C12	1.380 (4)	C5—C6	1.376 (5)
C11—C16	1.380 (4)	C6—C7	1.368 (5)
C12—C13	1.397 (4)	C7—C8	1.481 (4)
C13—C14	1.379 (5)	C9—C10	1.507 (4)
C14—C15	1.372 (6)	C3—H3	0.9300
C15—C16	1.366 (5)	C4—H4	0.9300
C18—C19	1.495 (4)	C5—H5	0.9300
C19—C23	1.383 (3)	C6—H6	0.9300
C19—C20	1.374 (3)	C9—H9A	0.9700
C20—C21	1.378 (4)	C9—H9B	0.9700
C12—O5—C24	118.3 (2)	N4—C21—H21	118.00
C10—O3—H3A	110.00	N4—C22—H22	118.00
N3—N2—C17	115.7 (2)	C23—C22—H22	118.00
N2—N3—C18	118.0 (2)	C22—C23—H23	121.00
C21—N4—C22	116.9 (2)	C19—C23—H23	121.00
C18—N3—H3B	121.00	O5—C24—H24C	109.00
N2—N3—H3B	121.00	H24B—C24—H24C	110.00
C1—N1—C9	123.6 (3)	H24A—C24—H24B	110.00
C1—N1—C8	111.8 (2)	H24A—C24—H24C	109.00
C8—N1—C9	124.3 (3)	O5—C24—H24B	109.00
C12—C11—C16	118.7 (3)	O5—C24—H24A	110.00
C16—C11—C17	120.9 (2)	O1—C1—N1	124.2 (3)
C12—C11—C17	120.4 (3)	O1—C1—C2	130.2 (3)
C11—C12—C13	120.6 (3)	N1—C1—C2	105.6 (3)
O5—C12—C13	123.3 (2)	C1—C2—C3	129.8 (3)
O5—C12—C11	116.1 (2)	C1—C2—C7	108.6 (3)
C12—C13—C14	118.4 (3)	C3—C2—C7	121.6 (3)
C13—C14—C15	121.7 (3)	C2—C3—C4	117.5 (3)
C14—C15—C16	118.8 (3)	C3—C4—C5	120.9 (3)
C11—C16—C15	121.8 (3)	C4—C5—C6	121.6 (4)
N2—C17—C11	119.4 (3)	C5—C6—C7	117.6 (4)
N3—C18—C19	116.0 (2)	C2—C7—C8	107.8 (3)
O6—C18—C19	120.7 (2)	C6—C7—C8	131.3 (3)
O6—C18—N3	123.2 (2)	C2—C7—C6	120.9 (3)
C18—C19—C23	122.3 (2)	O2—C8—C7	129.5 (3)
C20—C19—C23	118.4 (2)	N1—C8—C7	106.3 (3)
C18—C19—C20	119.2 (2)	O2—C8—N1	124.2 (3)
C19—C20—C21	118.6 (2)	N1—C9—C10	112.1 (2)
N4—C21—C20	123.7 (2)	O3—C10—C9	111.3 (2)
N4—C22—C23	123.6 (3)	O4—C10—C9	123.6 (2)
C19—C23—C22	118.8 (2)	O3—C10—O4	125.1 (3)
C12—C13—H13	121.00	C2—C3—H3	121.00
C14—C13—H13	121.00	C4—C3—H3	121.00
C15—C14—H14	119.00	C3—C4—H4	120.00
C13—C14—H14	119.00	C5—C4—H4	120.00
C16—C15—H15	121.00	C4—C5—H5	119.00
C14—C15—H15	121.00	C6—C5—H5	119.00
C11—C16—H16	119.00	C5—C6—H6	121.00
C15—C16—H16	119.00	C7—C6—H6	121.00
N2—C17—H17	120.00	N1—C9—H9A	109.00
C11—C17—H17	120.00	N1—C9—H9B	109.00
C21—C20—H20	121.00	C10—C9—H9A	109.00
C19—C20—H20	121.00	C10—C9—H9B	109.00
C20—C21—H21	118.00	H9A—C9—H9B	108.00
C24—O5—C12—C11	175.1 (3)	O6—C18—C19—C23	142.3 (3)
C24—O5—C12—C13	−3.7 (5)	O6—C18—C19—C20	−32.7 (4)
C17—N2—N3—C18	−167.0 (3)	N3—C18—C19—C23	−34.9 (4)
N3—N2—C17—C11	−175.9 (2)	N3—C18—C19—C20	150.1 (3)
N2—N3—C18—O6	1.1 (4)	C18—C19—C23—C22	−173.1 (3)
N2—N3—C18—C19	178.2 (2)	C23—C19—C20—C21	−0.3 (4)
C22—N4—C21—C20	1.6 (4)	C18—C19—C20—C21	174.9 (3)
C21—N4—C22—C23	0.2 (4)	C20—C19—C23—C22	1.9 (4)
C1—N1—C9—C10	−87.7 (4)	C19—C20—C21—N4	−1.6 (5)
C8—N1—C9—C10	85.4 (3)	N4—C22—C23—C19	−1.9 (4)
C8—N1—C1—C2	0.9 (3)	O1—C1—C2—C3	0.1 (6)
C9—N1—C1—O1	−4.7 (5)	O1—C1—C2—C7	178.7 (3)
C9—N1—C1—C2	174.7 (3)	N1—C1—C2—C3	−179.2 (3)
C1—N1—C8—O2	179.4 (3)	N1—C1—C2—C7	−0.7 (3)
C1—N1—C8—C7	−0.8 (3)	C1—C2—C3—C4	177.8 (3)
C9—N1—C8—O2	5.7 (5)	C7—C2—C3—C4	−0.6 (5)
C8—N1—C1—O1	−178.5 (3)	C1—C2—C7—C6	−178.6 (3)
C9—N1—C8—C7	−174.5 (2)	C1—C2—C7—C8	0.2 (3)
C17—C11—C12—C13	−175.8 (3)	C3—C2—C7—C6	0.1 (5)
C12—C11—C16—C15	−2.3 (5)	C3—C2—C7—C8	178.9 (3)
C17—C11—C12—O5	5.4 (4)	C2—C3—C4—C5	1.1 (5)
C12—C11—C17—N2	−165.6 (3)	C3—C4—C5—C6	−1.1 (6)
C16—C11—C17—N2	16.3 (4)	C4—C5—C6—C7	0.6 (5)
C17—C11—C16—C15	175.9 (3)	C5—C6—C7—C2	−0.1 (5)
C16—C11—C12—O5	−176.4 (3)	C5—C6—C7—C8	−178.6 (3)
C16—C11—C12—C13	2.4 (5)	C2—C7—C8—O2	−179.9 (3)
C11—C12—C13—C14	−1.1 (5)	C2—C7—C8—N1	0.3 (3)
O5—C12—C13—C14	177.7 (3)	C6—C7—C8—O2	−1.3 (6)
C12—C13—C14—C15	−0.5 (6)	C6—C7—C8—N1	179.0 (3)
C13—C14—C15—C16	0.7 (6)	N1—C9—C10—O3	176.9 (3)
C14—C15—C16—C11	0.8 (5)	N1—C9—C10—O4	−3.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N4i	0.82	1.86	2.681 (3)	177
N3—H3B···O6ii	0.86	2.12	2.958 (3)	164
C4—H4···O4iii	0.93	2.44	3.190 (4)	138
C20—H20···O3ii	0.93	2.57	3.500 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N4i	0.82	1.86	2.681 (3)	177
N3—H3B⋯O6ii	0.86	2.12	2.958 (3)	164
C4—H4⋯O4iii	0.93	2.44	3.190 (4)	138
C20—H20⋯O3ii	0.93	2.57	3.500 (4)	174

Symmetry codes: (i) ; (ii) ; (iii) .