2-[(4-Hydroxy-phen-yl)diazen-yl]benzoic acid-N,N'-bis-(4-pyridylmeth-yl)oxamide (2/1).

The asymmetric unit of the title co-crystal, 2C(13)H(10)N(2)O(3)·C(14)H(14)N(4)O(2), comprises one mol-ecule of 2-(4-hydroxy-phenyl-diazen-yl)benzoic acid and half of an N,N'-bis-(4-pyridylmeth-yl)oxamide mol-ecule as the latter is disposed about an inversion centre. The most notable feature of the crystal structure is the formation of supra-molecular chains arising from hydr-oxy-pyridine O-H⋯N contacts and amide-hydr-oxy C-H⋯O contacts. These give rise to 40-membered {⋯OH⋯NNC(4)OH⋯NC(4)NC(2)NH}(2) synthons, generating supra-molecular chains along [01]. The chains are connected into a two-dimensional array via C-H⋯π inter-actions. Layers, with a step-ladder topology, are consolidated into the crystal structure via further C-H⋯π inter-actions.

Related literature

For background to the co-crystallization of active pharmaceutical agents and a discussion on the definition of a co-crystal, see: Shan & Zaworotko (2008 ▶); Zukerman-Schpector & Tiekink (2008 ▶). For hydrogen-bonding considerations, see: Etter (1990 ▶). For related studies on co-crystal formation, see: Broker & Tiekink (2007 ▶); Broker et al. (2008 ▶); Ellis et al. (2009 ▶). For a related salt with 2-(4-hydroxy­phenyl­diazen­yl)n class="Chemical">benzoic acid, see: Corlette & Tiekink (2009 ▶). For related structures, see: Lee & Wang (2007 ▶); Qian & Huang (2005 ▶). For co-crystals of N,N′-bis­(4-pyridylmeth­yl)oxamide, see: Wilhelm et al. (2008 ▶).

Experimental

Crystal data

2C13H10N2O3·C14H14N4O2

M = 754.75

Triclinic,

a = 5.523 (3) Å

b = 11.132 (4) Å

c = 15.066 (7) Å

α = 72.748 (16)°

β = 88.92 (2)°

γ = 79.43 (2)°

V = 869.0 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 98 K

0.55 × 0.31 × 0.20 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.821, T max = 1

6882 measured reflections

3945 independent reflections

3477 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 1.08

3945 reflections

262 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049228/hg2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049228/hg2597Isup2.hkl

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

2C13H10N2O3·C14H14N4O2	Z = 1
Mr = 754.75	F(000) = 394
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.523 (3) Å	Cell parameters from 3695 reflections
b = 11.132 (4) Å	θ = 2.0–40.6°
c = 15.066 (7) Å	µ = 0.10 mm−1
α = 72.748 (16)°	T = 98 K
β = 88.92 (2)°	Block, red
γ = 79.43 (2)°	0.55 × 0.31 × 0.20 mm
V = 869.0 (7) Å3

Rigaku AFC12K/SATURN724 diffractometer	3945 independent reflections
Radiation source: fine-focus sealed tube	3477 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→7
Tmin = 0.821, Tmax = 1	k = −14→14
6882 measured reflections	l = −19→19

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3418P] where P = (Fo2 + 2Fc2)/3
3945 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.32 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	1.0476 (2)	−0.00128 (11)	0.38418 (8)	0.0287 (3)
O2	0.7677 (2)	0.68650 (12)	0.51985 (8)	0.0293 (3)
O3	0.5687 (2)	0.83724 (11)	0.40195 (8)	0.0264 (3)
H1O	0.5873	0.8673	0.3446	0.040*
O4	0.0094 (2)	1.33786 (11)	−0.01572 (8)	0.0298 (3)
H2O	0.0524	1.3892	−0.0638	0.045*
N1	0.8421 (3)	0.48340 (13)	0.16157 (9)	0.0268 (3)
N2	0.7290 (2)	0.10782 (13)	0.44396 (9)	0.0238 (3)
H1N	0.6700	0.1179	0.4965	0.029*
N3	0.7538 (2)	0.87835 (12)	0.24039 (9)	0.0222 (3)
N4	0.7707 (2)	0.94258 (12)	0.15667 (9)	0.0230 (3)
C1	0.6793 (3)	0.27688 (14)	0.28993 (10)	0.0216 (3)
C2	0.5771 (3)	0.32819 (15)	0.19998 (11)	0.0267 (3)
H2	0.4492	0.2940	0.1805	0.032*
C3	0.6641 (3)	0.42965 (16)	0.13916 (11)	0.0299 (4)
H3	0.5930	0.4631	0.0778	0.036*
C4	0.9377 (3)	0.43484 (15)	0.24874 (11)	0.0264 (3)
H4	1.0628	0.4723	0.2666	0.032*
C5	0.8634 (3)	0.33260 (15)	0.31435 (11)	0.0252 (3)
H5	0.9376	0.3011	0.3752	0.030*
C6	0.5892 (3)	0.16366 (15)	0.35621 (11)	0.0244 (3)
H6A	0.4150	0.1914	0.3693	0.029*
H6B	0.5944	0.0966	0.3250	0.029*
C7	0.9439 (3)	0.02757 (14)	0.44999 (10)	0.0221 (3)
C8	0.9611 (3)	0.71595 (14)	0.37441 (10)	0.0208 (3)
C9	0.9623 (3)	0.78081 (14)	0.27915 (10)	0.0212 (3)
C10	1.1625 (3)	0.74920 (15)	0.22689 (11)	0.0258 (3)
H10	1.1636	0.7929	0.1624	0.031*
C11	1.3589 (3)	0.65398 (16)	0.26952 (12)	0.0279 (4)
H11	1.4954	0.6330	0.2341	0.034*
C12	1.3583 (3)	0.58874 (15)	0.36356 (12)	0.0265 (3)
H12	1.4932	0.5229	0.3922	0.032*
C13	1.1604 (3)	0.61987 (15)	0.41561 (11)	0.0237 (3)
H13	1.1606	0.5753	0.4800	0.028*
C14	0.7599 (3)	0.74462 (14)	0.43795 (10)	0.0222 (3)
C15	0.5672 (3)	1.03918 (14)	0.11805 (10)	0.0224 (3)
C16	0.3394 (3)	1.05976 (15)	0.15929 (11)	0.0233 (3)
H16	0.3115	1.0047	0.2186	0.028*
C17	0.1561 (3)	1.16005 (15)	0.11346 (11)	0.0251 (3)
H17	0.0018	1.1737	0.1414	0.030*
C18	0.1956 (3)	1.24225 (15)	0.02580 (11)	0.0238 (3)
C19	0.4230 (3)	1.22184 (16)	−0.01495 (11)	0.0263 (3)
H19	0.4520	1.2777	−0.0738	0.032*
C20	0.6053 (3)	1.12046 (15)	0.03040 (11)	0.0252 (3)
H20	0.7582	1.1057	0.0018	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0295 (6)	0.0338 (6)	0.0211 (6)	0.0007 (5)	0.0015 (5)	−0.0098 (5)
O2	0.0308 (6)	0.0344 (6)	0.0189 (6)	−0.0012 (5)	0.0003 (5)	−0.0055 (5)
O3	0.0263 (6)	0.0291 (6)	0.0201 (5)	0.0010 (5)	0.0023 (4)	−0.0057 (5)
O4	0.0258 (6)	0.0295 (6)	0.0262 (6)	−0.0009 (5)	−0.0010 (5)	0.0011 (5)
N1	0.0282 (7)	0.0257 (6)	0.0233 (7)	−0.0017 (5)	0.0007 (5)	−0.0045 (5)
N2	0.0236 (7)	0.0273 (6)	0.0176 (6)	−0.0007 (5)	0.0000 (5)	−0.0048 (5)
N3	0.0253 (7)	0.0217 (6)	0.0183 (6)	−0.0034 (5)	−0.0022 (5)	−0.0044 (5)
N4	0.0268 (7)	0.0230 (6)	0.0194 (6)	−0.0057 (5)	−0.0020 (5)	−0.0059 (5)
C1	0.0209 (7)	0.0220 (7)	0.0210 (7)	0.0009 (5)	0.0006 (6)	−0.0080 (6)
C2	0.0292 (8)	0.0264 (7)	0.0245 (8)	−0.0034 (6)	−0.0056 (6)	−0.0085 (6)
C3	0.0388 (9)	0.0290 (8)	0.0190 (7)	−0.0020 (7)	−0.0059 (6)	−0.0049 (6)
C4	0.0223 (7)	0.0269 (7)	0.0280 (8)	−0.0019 (6)	−0.0033 (6)	−0.0066 (6)
C5	0.0237 (8)	0.0273 (7)	0.0212 (7)	−0.0008 (6)	−0.0038 (6)	−0.0045 (6)
C6	0.0237 (7)	0.0269 (7)	0.0207 (7)	−0.0029 (6)	−0.0025 (6)	−0.0053 (6)
C7	0.0233 (7)	0.0217 (7)	0.0212 (8)	−0.0055 (6)	0.0013 (6)	−0.0054 (6)
C8	0.0211 (7)	0.0209 (7)	0.0211 (7)	−0.0044 (5)	−0.0010 (6)	−0.0071 (6)
C9	0.0226 (7)	0.0206 (7)	0.0204 (7)	−0.0044 (6)	−0.0025 (6)	−0.0059 (6)
C10	0.0289 (8)	0.0261 (7)	0.0205 (7)	−0.0036 (6)	0.0026 (6)	−0.0054 (6)
C11	0.0249 (8)	0.0308 (8)	0.0290 (8)	−0.0035 (6)	0.0046 (6)	−0.0114 (7)
C12	0.0231 (8)	0.0269 (7)	0.0277 (8)	0.0003 (6)	−0.0043 (6)	−0.0079 (6)
C13	0.0249 (8)	0.0254 (7)	0.0204 (7)	−0.0045 (6)	−0.0031 (6)	−0.0064 (6)
C14	0.0252 (8)	0.0222 (7)	0.0198 (7)	−0.0052 (6)	−0.0013 (6)	−0.0067 (6)
C15	0.0267 (8)	0.0228 (7)	0.0186 (7)	−0.0059 (6)	−0.0023 (6)	−0.0063 (6)
C16	0.0253 (8)	0.0247 (7)	0.0197 (7)	−0.0073 (6)	−0.0008 (6)	−0.0045 (6)
C17	0.0222 (7)	0.0274 (7)	0.0248 (8)	−0.0061 (6)	0.0004 (6)	−0.0055 (6)
C18	0.0246 (8)	0.0238 (7)	0.0226 (7)	−0.0045 (6)	−0.0042 (6)	−0.0059 (6)
C19	0.0290 (8)	0.0281 (8)	0.0186 (7)	−0.0058 (6)	0.0002 (6)	−0.0016 (6)
C20	0.0256 (8)	0.0290 (8)	0.0201 (7)	−0.0046 (6)	0.0003 (6)	−0.0063 (6)

O1—C7	1.2304 (19)	C6—H6B	0.9900
O2—C14	1.2088 (19)	C7—C7i	1.542 (3)
O3—C14	1.3276 (19)	C8—C13	1.393 (2)
O3—H1O	0.8402	C8—C9	1.403 (2)
O4—C18	1.3450 (19)	C8—C14	1.505 (2)
O4—H2O	0.8401	C9—C10	1.398 (2)
N1—C3	1.337 (2)	C10—C11	1.383 (2)
N1—C4	1.340 (2)	C10—H10	0.9500
N2—C7	1.335 (2)	C11—C12	1.387 (2)
N2—C6	1.451 (2)	C11—H11	0.9500
N2—H1N	0.8801	C12—C13	1.386 (2)
N3—N4	1.2632 (19)	C12—H12	0.9500
N3—C9	1.427 (2)	C13—H13	0.9500
N4—C15	1.403 (2)	C15—C20	1.399 (2)
C1—C2	1.390 (2)	C15—C16	1.404 (2)
C1—C5	1.391 (2)	C16—C17	1.379 (2)
C1—C6	1.516 (2)	C16—H16	0.9500
C2—C3	1.384 (2)	C17—C18	1.405 (2)
C2—H2	0.9500	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.398 (2)
C4—C5	1.389 (2)	C19—C20	1.381 (2)
C4—H4	0.9500	C19—H19	0.9500
C5—H5	0.9500	C20—H20	0.9500
C6—H6A	0.9900
C14—O3—H1O	108.7	C10—C9—N3	123.07 (14)
C18—O4—H2O	112.5	C8—C9—N3	116.96 (13)
C3—N1—C4	116.75 (14)	C11—C10—C9	119.74 (15)
C7—N2—C6	120.86 (13)	C11—C10—H10	120.1
C7—N2—H1N	116.6	C9—C10—H10	120.1
C6—N2—H1N	122.1	C10—C11—C12	120.63 (15)
N4—N3—C9	115.26 (13)	C10—C11—H11	119.7
N3—N4—C15	115.72 (13)	C12—C11—H11	119.7
C2—C1—C5	117.49 (14)	C13—C12—C11	119.81 (15)
C2—C1—C6	119.45 (14)	C13—C12—H12	120.1
C5—C1—C6	123.05 (14)	C11—C12—H12	120.1
C3—C2—C1	119.17 (16)	C12—C13—C8	120.65 (15)
C3—C2—H2	120.4	C12—C13—H13	119.7
C1—C2—H2	120.4	C8—C13—H13	119.7
N1—C3—C2	123.90 (15)	O2—C14—O3	119.58 (14)
N1—C3—H3	118.0	O2—C14—C8	122.19 (14)
C2—C3—H3	118.0	O3—C14—C8	118.23 (13)
N1—C4—C5	123.41 (16)	C20—C15—N4	114.33 (14)
N1—C4—H4	118.3	C20—C15—C16	119.49 (14)
C5—C4—H4	118.3	N4—C15—C16	126.18 (14)
C4—C5—C1	119.28 (15)	C17—C16—C15	119.85 (15)
C4—C5—H5	120.4	C17—C16—H16	120.1
C1—C5—H5	120.4	C15—C16—H16	120.1
N2—C6—C1	114.78 (14)	C16—C17—C18	120.54 (15)
N2—C6—H6A	108.6	C16—C17—H17	119.7
C1—C6—H6A	108.6	C18—C17—H17	119.7
N2—C6—H6B	108.6	O4—C18—C19	122.69 (14)
C1—C6—H6B	108.6	O4—C18—C17	117.82 (14)
H6A—C6—H6B	107.5	C19—C18—C17	119.49 (14)
O1—C7—N2	125.14 (15)	C20—C19—C18	119.95 (15)
O1—C7—C7i	121.86 (17)	C20—C19—H19	120.0
N2—C7—C7i	112.99 (16)	C18—C19—H19	120.0
C13—C8—C9	119.19 (14)	C19—C20—C15	120.66 (15)
C13—C8—C14	116.22 (14)	C19—C20—H20	119.7
C9—C8—C14	124.57 (14)	C15—C20—H20	119.7
C10—C9—C8	119.98 (14)
C9—N3—N4—C15	−179.67 (12)	C9—C10—C11—C12	0.5 (3)
C5—C1—C2—C3	0.9 (2)	C10—C11—C12—C13	−0.6 (3)
C6—C1—C2—C3	−178.53 (14)	C11—C12—C13—C8	0.2 (2)
C4—N1—C3—C2	−0.5 (2)	C9—C8—C13—C12	0.3 (2)
C1—C2—C3—N1	−0.5 (3)	C14—C8—C13—C12	−178.21 (14)
C3—N1—C4—C5	0.9 (2)	C13—C8—C14—O2	−1.2 (2)
N1—C4—C5—C1	−0.5 (2)	C9—C8—C14—O2	−179.56 (15)
C2—C1—C5—C4	−0.5 (2)	C13—C8—C14—O3	178.70 (14)
C6—C1—C5—C4	178.93 (14)	C9—C8—C14—O3	0.3 (2)
C7—N2—C6—C1	−79.82 (19)	N3—N4—C15—C20	171.10 (13)
C2—C1—C6—N2	172.60 (14)	N3—N4—C15—C16	−8.5 (2)
C5—C1—C6—N2	−6.8 (2)	C20—C15—C16—C17	−0.4 (2)
C6—N2—C7—O1	3.7 (2)	N4—C15—C16—C17	179.19 (15)
C6—N2—C7—C7i	−176.57 (15)	C15—C16—C17—C18	−0.2 (2)
C13—C8—C9—C10	−0.4 (2)	C16—C17—C18—O4	179.60 (14)
C14—C8—C9—C10	178.01 (14)	C16—C17—C18—C19	0.0 (2)
C13—C8—C9—N3	180.00 (13)	O4—C18—C19—C20	−178.74 (15)
C14—C8—C9—N3	−1.6 (2)	C17—C18—C19—C20	0.9 (2)
N4—N3—C9—C10	−5.8 (2)	C18—C19—C20—C15	−1.5 (2)
N4—N3—C9—C8	173.84 (13)	N4—C15—C20—C19	−178.39 (14)
C8—C9—C10—C11	0.0 (2)	C16—C15—C20—C19	1.2 (2)
N3—C9—C10—C11	179.58 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1o···N3	0.84	1.79	2.568 (2)	154
N2—H1n···O3ii	0.88	2.11	2.966 (2)	163
O4—H2o···N1iii	0.84	1.88	2.720 (2)	173
C5—H5···O2iv	0.95	2.34	3.187 (3)	148
C6—H6a···O2ii	0.99	2.54	3.265 (3)	130
C2—H2···Cg(3)v	0.95	2.76	3.542 (3)	140
C4—H4···Cg(2)	0.95	2.87	3.684 (3)	145
C11—H11···Cg(1)vi	0.95	2.96	3.642 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1o⋯N3	0.84	1.79	2.568 (2)	154
N2—H1n⋯O3i	0.88	2.11	2.966 (2)	163
O4—H2o⋯N1ii	0.84	1.88	2.720 (2)	173
C5—H5⋯O2iii	0.95	2.34	3.187 (3)	148
C6—H6a⋯O2i	0.99	2.54	3.265 (3)	130
C2—H2⋯Cg(3)iv	0.95	2.76	3.542 (3)	140
C4—H4⋯Cg(2)	0.95	2.87	3.684 (3)	145
C11—H11⋯Cg(1)v	0.95	2.96	3.642 (3)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg(1), Cg(2) and Cg(3) are the centroids of the N1,C2–C5, C8–C13 and C15–C20 rings, respectively.