Form II of adipic acid-nicotinohydrazide (1/2).

The crystal structure of the title co-crystal, 2C(6)H(7)N(3)O·C(6)H(10)O(4), is a second polymorph, designated form II, of the co-crystal formed between the two mol-ecules [Lemmerer et al. (2011 ▶). CrystEngComm, 13, 55-59]. The asymmetric unit comprises one mol-ecule of nicotinic acid hydrazide, and one half-mol-ecule of adipic acid (the entire mol-ecule is completed by the application of a centre of inversion). In the crystal, mol-ecules assemble into a three-dimensional network of hydrogen bonds, formed by three N-H⋯O hydrogen bonds and one O-H⋯N hydrogen bond. The O-H⋯N hydrogen bond formed between the carboxyl group and the pyridine ring is supported by a C-H⋯O hydrogen bond.

Related literature

For the first polymorph, see: Lemmerer et al. (2011 ▶). For experimental techniques, see: Friščić et al. (2009 ▶); Skovsgaard & Bond (2009 ▶); Karki et al. (2009 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C6H7N3O·C6H10O4

M = 420.43

Monoclinic,

a = 15.9747 (4) Å

b = 7.3309 (2) Å

c = 8.7451 (2) Å

β = 103.729 (3)°

V = 994.87 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.32 × 0.28 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini ultra Mo) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.92, T max = 0.98

6207 measured reflections

1845 independent reflections

1487 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.02

1845 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054043/tk5035sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054043/tk5035Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054043/tk5035Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811054043/tk5035Isup4.cml

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

2C6H7N3O·C6H10O4	F(000) = 444
Mr = 420.43	Dx = 1.403 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3572 reflections
a = 15.9747 (4) Å	θ = 3.1–28.5°
b = 7.3309 (2) Å	µ = 0.11 mm−1
c = 8.7451 (2) Å	T = 173 K
β = 103.729 (3)°	Block, colourless
V = 994.87 (4) Å3	0.32 × 0.28 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini ultra Mo) detector	1487 reflections with I > 2σ(I)
ω scans	Rint = 0.020
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	θmax = 25.5°, θmin = 3.1°
Tmin = 0.92, Tmax = 0.98	h = −13→19
6207 measured reflections	k = −8→8
1845 independent reflections	l = −10→9

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.029	(Δ/σ)max < 0.001
wR(F2) = 0.077	Δρmax = 0.18 e Å−3
S = 1.02	Δρmin = −0.14 e Å−3
1845 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
153 parameters	Extinction coefficient: 0.0095 (18)
0 restraints

Experimental. Absorption corrections were made using the program Crysalis Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm in CrysAlisPro.

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.

	x	y	z	Uiso*/Ueq
C1	0.16016 (7)	0.37907 (15)	0.35826 (13)	0.0237 (3)
C2	0.22411 (7)	0.44813 (15)	0.47997 (13)	0.0248 (3)
H2A	0.2294	0.5767	0.4922	0.03*
C3	0.27134 (8)	0.16066 (15)	0.56223 (15)	0.0296 (3)
H3	0.3105	0.0841	0.6326	0.036*
C4	0.20920 (8)	0.08110 (15)	0.44526 (15)	0.0317 (3)
H4	0.2056	−0.0479	0.4355	0.038*
C5	0.15231 (8)	0.19064 (16)	0.34265 (14)	0.0291 (3)
H5	0.1082	0.1384	0.2622	0.035*
C6	0.09817 (8)	0.49832 (15)	0.24735 (13)	0.0243 (3)
N1	0.13026 (7)	0.65323 (12)	0.20370 (11)	0.0259 (2)
H1	0.1859 (9)	0.6738 (17)	0.2300 (15)	0.030 (3)*
N2	0.27881 (6)	0.34156 (13)	0.58100 (11)	0.0276 (3)
N3	0.07997 (7)	0.77311 (15)	0.09121 (13)	0.0303 (3)
H3A	0.0389 (9)	0.8250 (17)	0.1382 (16)	0.036 (4)*
H3B	0.0508 (9)	0.7022 (19)	0.0145 (18)	0.042 (4)*
O1	0.02225 (5)	0.45309 (11)	0.19861 (10)	0.0327 (2)
C7	0.38377 (7)	0.67377 (15)	0.82289 (13)	0.0259 (3)
C8	0.45756 (8)	0.75709 (16)	0.94010 (16)	0.0352 (3)
H8A	0.5119	0.7085	0.9206	0.042*
H8B	0.4543	0.7172	1.0467	0.042*
C9	0.46178 (7)	0.96301 (15)	0.93861 (14)	0.0281 (3)
H9A	0.4079	1.0133	0.9588	0.034*
H9B	0.466	1.0045	0.833	0.034*
O2	0.39428 (6)	0.49783 (11)	0.80455 (11)	0.0341 (2)
O3	0.32068 (5)	0.75783 (10)	0.75195 (11)	0.0353 (2)
H2	0.3478 (12)	0.449 (2)	0.727 (2)	0.069 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0214 (6)	0.0264 (6)	0.0251 (6)	−0.0031 (5)	0.0090 (5)	−0.0026 (5)
C2	0.0240 (6)	0.0226 (6)	0.0279 (7)	−0.0018 (5)	0.0062 (5)	−0.0018 (5)
C3	0.0293 (7)	0.0270 (7)	0.0342 (7)	0.0028 (5)	0.0105 (6)	0.0043 (5)
C4	0.0374 (8)	0.0216 (6)	0.0387 (7)	−0.0023 (5)	0.0144 (6)	−0.0018 (5)
C5	0.0280 (7)	0.0281 (6)	0.0317 (7)	−0.0065 (5)	0.0083 (5)	−0.0057 (5)
C6	0.0221 (7)	0.0279 (6)	0.0231 (6)	−0.0031 (5)	0.0055 (5)	−0.0062 (4)
N1	0.0207 (6)	0.0276 (6)	0.0280 (6)	−0.0013 (4)	0.0030 (5)	0.0001 (4)
N2	0.0245 (6)	0.0274 (6)	0.0301 (6)	−0.0012 (4)	0.0048 (4)	0.0009 (4)
N3	0.0284 (6)	0.0319 (6)	0.0290 (6)	0.0001 (5)	0.0038 (5)	0.0023 (5)
O1	0.0232 (5)	0.0372 (5)	0.0346 (5)	−0.0062 (4)	0.0010 (4)	0.0019 (4)
C7	0.0228 (7)	0.0276 (7)	0.0266 (6)	0.0012 (5)	0.0042 (5)	0.0027 (5)
C8	0.0291 (7)	0.0348 (8)	0.0350 (7)	0.0021 (5)	−0.0058 (6)	−0.0030 (5)
C9	0.0206 (7)	0.0321 (7)	0.0292 (7)	0.0011 (5)	0.0014 (5)	−0.0023 (5)
O2	0.0296 (5)	0.0276 (5)	0.0382 (6)	0.0027 (4)	−0.0059 (4)	−0.0015 (4)
O3	0.0244 (5)	0.0306 (5)	0.0444 (5)	0.0030 (4)	−0.0047 (4)	0.0000 (4)

C1—C2	1.3845 (16)	N1—H1	0.877 (14)
C1—C5	1.3908 (15)	N3—H3A	0.934 (14)
C1—C6	1.4932 (16)	N3—H3B	0.888 (15)
C2—N2	1.3371 (15)	C7—O3	1.2180 (13)
C2—H2A	0.95	C7—O2	1.3154 (13)
C3—N2	1.3382 (15)	C7—C8	1.4965 (17)
C3—C4	1.3747 (18)	C8—C9	1.5113 (16)
C3—H3	0.95	C8—H8A	0.99
C4—C5	1.3744 (17)	C8—H8B	0.99
C4—H4	0.95	C9—C9i	1.522 (2)
C5—H5	0.95	C9—H9A	0.99
C6—O1	1.2317 (14)	C9—H9B	0.99
C6—N1	1.3383 (15)	O2—H2	0.950 (19)
N1—N3	1.4178 (14)
C2—C1—C5	118.13 (10)	C2—N2—C3	118.21 (10)
C2—C1—C6	122.68 (10)	N1—N3—H3A	106.8 (8)
C5—C1—C6	119.16 (10)	N1—N3—H3B	105.7 (9)
N2—C2—C1	122.79 (10)	H3A—N3—H3B	105.8 (12)
N2—C2—H2A	118.6	O3—C7—O2	123.24 (11)
C1—C2—H2A	118.6	O3—C7—C8	124.36 (10)
N2—C3—C4	122.64 (11)	O2—C7—C8	112.40 (10)
N2—C3—H3	118.7	C7—C8—C9	115.55 (10)
C4—C3—H3	118.7	C7—C8—H8A	108.4
C5—C4—C3	119.13 (11)	C9—C8—H8A	108.4
C5—C4—H4	120.4	C7—C8—H8B	108.4
C3—C4—H4	120.4	C9—C8—H8B	108.4
C4—C5—C1	119.08 (11)	H8A—C8—H8B	107.5
C4—C5—H5	120.5	C8—C9—C9i	112.33 (12)
C1—C5—H5	120.5	C8—C9—H9A	109.1
O1—C6—N1	122.82 (11)	C9i—C9—H9A	109.1
O1—C6—C1	120.92 (10)	C8—C9—H9B	109.1
N1—C6—C1	116.25 (10)	C9i—C9—H9B	109.1
C6—N1—N3	122.12 (10)	H9A—C9—H9B	107.9
C6—N1—H1	120.3 (8)	C7—O2—H2	110.9 (10)
N3—N1—H1	116.6 (8)
C5—C1—C2—N2	0.84 (16)	C5—C1—C6—N1	−143.68 (10)
C6—C1—C2—N2	178.88 (10)	O1—C6—N1—N3	−3.28 (17)
N2—C3—C4—C5	0.17 (17)	C1—C6—N1—N3	175.83 (10)
C3—C4—C5—C1	1.15 (17)	C1—C2—N2—C3	0.45 (15)
C2—C1—C5—C4	−1.61 (15)	C4—C3—N2—C2	−0.97 (15)
C6—C1—C5—C4	−179.73 (10)	O3—C7—C8—C9	−14.84 (18)
C2—C1—C6—O1	−142.57 (11)	O2—C7—C8—C9	165.28 (10)
C5—C1—C6—O1	35.46 (15)	C7—C8—C9—C9i	179.74 (12)
C2—C1—C6—N1	38.30 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ii	0.877 (14)	2.174 (15)	3.0409 (14)	169.7 (11)
N3—H3A···O1iii	0.934 (14)	2.129 (14)	3.0349 (14)	163.0 (12)
N3—H3B···O1iv	0.888 (15)	2.258 (16)	3.1426 (14)	173.7 (13)
O2—H2···N2	0.950 (19)	1.671 (19)	2.6126 (13)	170.3 (16)
C2—H2A···O3	0.95	2.73	3.3838 (14)	126.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.877 (14)	2.174 (15)	3.0409 (14)	169.7 (11)
N3—H3A⋯O1ii	0.934 (14)	2.129 (14)	3.0349 (14)	163.0 (12)
N3—H3B⋯O1iii	0.888 (15)	2.258 (16)	3.1426 (14)	173.7 (13)
O2—H2⋯N2	0.950 (19)	1.671 (19)	2.6126 (13)	170.3 (16)
C2—H2A⋯O3	0.95	2.73	3.3838 (14)	126

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