Form II of adipic acid–nicotinohydrazide (1/2)

Lemmerer, A.; Bernstein, J.; Kahlenberg, V.

doi:10.1107/S1600536811054043

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Volume 68| Part 1| January 2012| Page o190

doi:10.1107/S1600536811054043

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Form II of adipic acid–nicotinohydrazide (1/2)

Andreas Lemmerer,^a ^* Joel Bernstein ^b and Volker Kahlenberg ^c

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa, ^bFaculty of Science, NYU Abu Dhabi, PO Box 129188, Abu Dhabi, United Arab Emirates, and ^cInstitute of Mineralogy and Petrography, University of Innsbruck, Innsbruck 6020, Austria
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

(Received 12 December 2011; accepted 15 December 2011; online 21 December 2011)

The crystal structure of the title co-crystal, 2C₆H₇N₃O·C₆H₁₀O₄, is a second polymorph, designated form II, of the co-crystal formed between the two molecules [Lemmerer et al. (2011 ). CrystEngComm, 13, 55–59]. The asymmetric unit comprises one molecule of nicotinic acid hydrazide, and one half-molecule of adipic acid (the entire molecule is completed by the application of a centre of inversion). In the crystal, molecules 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_r = 420.43
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.02
1845 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811054043/tk5035sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054043/tk5035Isup3.mol

Supporting information file. DOI: 10.1107/S1600536811054043/tk5035Isup4.cml

checkCIF report

Comment top

Form I of the title compound was obtained by solution crystallization, where 1 equivalent of adipic acid was dissolved with two equivalents of niazid in methanol, and then the solution left to slowly evaporate over a few days (Lemmerer et al., 2011). The ratio of the two starting materials was determined by the two expected primary hydrogen bond interactions, namely the two carboxylic acids hydrogen bonding to the single pyridine of two niazid molecules. Form II was obtained by first grinding the two starting materials in the same stoichiometric ratio as form I for 20 minutes, followed by conventional solution crystallization by dissolving the ground powder in methanol. Crystals were obtained after a few days from the methanol solution. Obtaining polymorphs by either grinding or solution crystallization is a focus of recent research (Friščić et al., 2009; Skovsgaard & Bond, 2009; Karki et al., 2009).

The crystallographic asymmetric unit of the resulting crystal structure of form II reflects this stoichiometry, containing one niazid molecule in a general position and one half adipic acid molecule on a special position (Fig. 1). The two molecules lie approximately co-planar. The expected heterosynthon is formed between two niazid and one adipic acid molecule lying on a crystallographic center of symmetry (which requires the pyridine ring and carboxylic acid to be co-planar). The heterosynthon between the dicarboxylic acid molecule and the pyridine ring is formed by a O—H···N hydrogen bond, as well as a C—H···O hydrogen bond, to form a R²₂(7) ring (Bernstein et al., 1995). The niazid molecules are connected by a centrosymmetric R²₂(10) ring using N—H···O hydrogen bonds from one of the amine H atoms. Adjacent dimers are joined by a N—H···O bond using the second amine H atom, which together with the C—H···O hydrogen bond and the N—H···O hydrogen bond from the amide H forms a R²₄(13) ring (Fig. 2). Hence, all four H bond donors are used to form a 3-D network. In form I, the same R²₂(7) ring is observed but the amide H atom forms a C(4) chain to form a 2-D sheet, which is then connected into a 3-D network by the amine H atoms hydrogen bonding to adjacent sheets (Lemmerer et al., 2011).

Related literature top

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 top

A stoichiometric amount in the ratio of 2:1 of nicotinic acid hydrazide to adipic acid was ground together in a mortar with a pestle under the drop-wise addition of methanol over 20 minutes. The resulting powder was then dissolved in 10 ml of AR-grade methanol, and the solution slowly left to evaporate to afford colourless block-like crystals after one week.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); 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).

Figures top

	Fig. 1. The asymmetric unit of (I) extended to show the entire dicarboxylic acid and showing the atomic numbering scheme. Displacement ellipsoids are shown at the 50% probability level. Symmetry code: (i): -x, -y, -z.
	Fig. 2. Hydrogen bonding diagram of (I), Form II, showing the various ring shaped hydrogen bonding motifs. Intermolecular N—H···N, O—H···N and C—H···O hydrogen bonds are shown as dashed red lines.

adipic acid–nicotinohydrazide (1/2) top

Crystal data top

2C₆H₇N₃O·C₆H₁₀O₄	F(000) = 444
M_r = 420.43	D_x = 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

Data collection top

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

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.048P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.029	(Δ/σ)_max < 0.001
wR(F²) = 0.077	Δρ_max = 0.18 e Å⁻³
S = 1.02	Δρ_min = −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

Crystal data top

2C₆H₇N₃O·C₆H₁₀O₄	V = 994.87 (4) Å³
M_r = 420.43	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.9747 (4) Å	µ = 0.11 mm⁻¹
b = 7.3309 (2) Å	T = 173 K
c = 8.7451 (2) Å	0.32 × 0.28 × 0.04 mm
β = 103.729 (3)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini ultra Mo) detector	1845 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	1487 reflections with I > 2σ(I)
T_min = 0.92, T_max = 0.98	R_int = 0.020
6207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.18 e Å⁻³
1845 reflections	Δρ_min = −0.14 e Å⁻³
153 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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: (ii) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	2C₆H₇N₃O·C₆H₁₀O₄
M_r	420.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	15.9747 (4), 7.3309 (2), 8.7451 (2)
β (°)	103.729 (3)
V (Å³)	994.87 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.28 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini ultra Mo) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.92, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	6207, 1845, 1487
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.02
No. of reflections	1845
No. of parameters	153
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	126.2

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y+1, −z.

Acknowledgements

This work was supported in part by grant No. 2004118 from the United States–Israel Binational Science Foundation (Jerusalem). AL thanks the South African National Research Foundation for a postdoctoral scholarship (SFP2007070400002) and the Oppenheimer Memorial Trust for financial support, and the Molecular Sciences Institute for infrastucture.

References

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