2-[(4-Hydroxy­phen­yl)diazen­yl]benzoic acid–N,N′-bis­(4-pyridylmeth­yl)oxamide (2/1)

Arman, H.D.; Miller, T.; Poplaukhin, P.; Tiekink, E.R.T.

doi:10.1107/S1600536809049228

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3178-o3179

doi:10.1107/S1600536809049228

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2-[(4-Hydroxyphenyl)diazenyl]benzoic acid–N,N′-bis(4-pyridylmethyl)oxamide (2/1)

Hadi D. Arman,^a Tyler Miller,^a Pavel Poplaukhin ^b and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, ^bChemical Abstracts Service, 2540 Olentangy River Rd, Columbus, Ohio 43202, USA, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 November 2009; accepted 18 November 2009; online 21 November 2009)

The asymmetric unit of the title co-crystal, 2C₁₃H₁₀N₂O₃·C₁₄H₁₄N₄O₂, comprises one molecule of 2-(4-hydroxyphenyldiazenyl)benzoic acid and half of an N,N′-bis(4-pyridylmethyl)oxamide molecule as the latter is disposed about an inversion centre. The most notable feature of the crystal structure is the formation of supramolecular chains arising from hydroxy–pyridine O—H⋯N contacts and amide–hydroxy C—H⋯O contacts. These give rise to 40-membered {⋯OH⋯NNC₄OH⋯NC₄NC₂NH}₂ synthons, generating supramolecular chains along [01 $[\overline{1}]$ ]. The chains are connected into a two-dimensional array via C—H⋯π interactions. Layers, with a step-ladder topology, are consolidated into the crystal structure via further C—H⋯π interactions.

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)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_r = 754.75
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.143
S = 1.08
3945 reflections
262 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z; (iii) -x+2, -y+1, -z+1; (iv) x, y-1, z; (v) x+1, y, z. Cg(1), Cg(2) and Cg(3) are the centroids of the N1,C2–C5, C8–C13 and C15–C20 rings, respectively.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Co-crystallization of active pharmaceutical ingredients (Shan & Zaworotko, 2008) remains an active area of crystal engineering; see Zukerman-Schpector & Tiekink (2008) for terminology. As a continuation of studies into co-crystallization (Broker & Tiekink, 2007; Broker et al., 2008; Ellis et al., 2009), aimed at establishing a hierarchy of hydrogen bonding (Etter, 1990), the co-crystallization of 2-(4-hydroxyphenyldiazenyl)benzoic acid with N,N'-bis(4-pyridylmethyl)oxamide was investigated.

The title 2:1 co-crystal, (I), comprises a molecule of 2-(4-hydroxyphenyldiazenyl)benzoic acid (Fig. 1) and half a molecule of N,N'-bis(4-pyridylmethyl)oxamide as the latter is disposed about a centre of inversion (Fig. 2). The geometric parameters associated with the benzoic acid derivative in (I), including the intramolecular O—H_hydroxyl···N_diazenyl hydrogen bond, Table 1, is consistent with that observed in the crystal structure of its hydrate (Qian & Huang, 2005). Similarly, the conformation of the N,N'-bis(4-pyridylmethyl)oxamide molecule is akin to those exhibited by the two independent molecules in its pure form (Lee & Wang, 2007). Unlike 2-(4-hydroxyphenyldiazenyl)benzoic (Corlette & Tiekink, 2009), the oxamide derivative has been investigated in several co-crystallization studies (e.g. Wilhelm et al., 2008).

The primary contacts between molecules occur between the hydroxyl-O4—H···pyridine-N1 and N2-amide···O3-hydroxyl atoms. These combine to form 40-membered {···OH···NNC₄OH···NC₄NC₂NH}₂ synthons to generate supramolecular chains with base vector [0 1 1], Fig. 3. Chains are connected into a 2-D array via pyridine-C5—H···O2-carbonyl and pyridine-C2—H···π interactions, where the π-system is the (C15—C20 ring); Table 1 and Fig. 4. Layers, with a step-ladder topology, are consolidated into the crystal structure via further C—H···π interactions, Table 1 and Fig. 5.

Related literature top

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)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). Cg(1), Cg(2) and Cg(3) are the centroids of the N1,C2–C5, C8–C13 and C15–C20 rings, respectively.

Experimental top

Red crystals of (I) were isolated from the co-crystallization of 1:1 molar equivalents of 2-(4-hydroxyphenyldiazenyl)benzoic and N,N'-bis(4-pyridylmethyl)oxamide in an ethanol/chloroform mixture (1/1 v/v).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

	Fig. 1. Molecular structure of 2-(4-hydroxyphenyldiazenyl)benzoic acid, one of the components of co-crystal (I), showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Molecular structure of N,N'-bis(4-pyridylmethyl)oxamide, one of the components of co-crystal (I), showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. The molecule is located about a crystallographic centre of inversion. Symmetry operation i: 2 - x, -y, 1 - z.
	Fig. 3. A view of a supramolecular chain mediated by O—H···N and N—H···O (orange dashed lines) hydrogen bonding showing the 40-membered {···OH···NNC₄OH···NC₄NC₂NH}₂ synthons. Colour code: S, yellow; O,red; N, blue; C, grey; and H, green.
	Fig. 4. A side-on view of a layer whereby the chains shown in Figure 3 are connected to off-set chains via C—H···O (green dashed lines) and C—H···π (purple dashed lines with the ring centroid represented as a purple sphere) interactions. Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.
	Fig. 5. View of the stacking of layers in (I). Layers are connected by C—H···π interactions, the shortest of these is represented as purple dashed lines with each ring centroid indicated by a purple sphere. Colour code: S, yellow; O, red; N, blue; C, grey; and H, green.

2-[(4-Hydroxyphenyl)diazenyl]benzoic acid–N,N'-bis(4-pyridylmethyl)oxamide (2/1) top

Crystal data top

2C₁₃H₁₀N₂O₃·C₁₄H₁₄N₄O₂	Z = 1
M_r = 754.75	F(000) = 394
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0675P)² + 0.3418P] where P = (F_o² + 2F_c²)/3
3945 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.32 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

2C₁₃H₁₀N₂O₃·C₁₄H₁₄N₄O₂	γ = 79.43 (2)°
M_r = 754.75	V = 869.0 (7) Å³
Triclinic, P1	Z = 1
a = 5.523 (3) Å	Mo Kα radiation
b = 11.132 (4) Å	µ = 0.10 mm⁻¹
c = 15.066 (7) Å	T = 98 K
α = 72.748 (16)°	0.55 × 0.31 × 0.20 mm
β = 88.92 (2)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3945 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3477 reflections with I > 2σ(I)
T_min = 0.821, T_max = 1	R_int = 0.033
6882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	3 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.08	Δρ_max = 0.32 e Å⁻³
3945 reflections	Δρ_min = −0.28 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z+1; (v) x, y−1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	2C₁₃H₁₀N₂O₃·C₁₄H₁₄N₄O₂
M_r	754.75
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	5.523 (3), 11.132 (4), 15.066 (7)
α, β, γ (°)	72.748 (16), 88.92 (2), 79.43 (2)
V (Å³)	869.0 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.31 × 0.20

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.821, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	6882, 3945, 3477
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.08
No. of reflections	3945
No. of parameters	262
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z; (iii) −x+2, −y+1, −z+1; (iv) x, y−1, z; (v) x+1, y, z.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887. Web of Science CSD CrossRef CAS Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096–1109. Web of Science CSD CrossRef CAS Google Scholar
Corlette, E. M. & Tiekink, E. R. T. (2009). J. Chem. Crystallogr. 39, 603–606. Web of Science CSD CrossRef CAS Google Scholar
Ellis, C. A., Miller, M. A., Spencer, J., Zukerman-Schpector, J. & Tiekink, E. R. T. (2009). CrystEngComm, 11, 1352–1361. Web of Science CSD CrossRef CAS Google Scholar
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Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
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Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Shan, N. & Zaworotko, M. J. (2008). Drug Discovery Today, 13, 440–446. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Wilhelm, C., Boyd, S. A., Chawda, S., Fowler, F. W., Goroff, N. S., Halada, G. P., Grey, C. P., Lauher, J. W., Luo, L., Martin, C. D., Parise, J. B., Tarabrella, C. & Webb, J. A. (2008). J. Am. Chem. Soc. 130, 4415–4420. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 65| Part 12| December 2009| Pages o3178-o3179

doi:10.1107/S1600536809049228

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

2-[(4-Hy­droxy­phen­yl)diazen­yl]benzoic acid–N,N′-bis­­(4-pyridylmeth­yl)oxamide (2/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

2-[(4-Hydroxyphenyl)diazenyl]benzoic acid–N,N′-bis(4-pyridylmethyl)oxamide (2/1)