Isonicotinamide–formamide (1/1)

Oswald, I.D.H.; Motherwell, W.D.S.; Parsons, S.

doi:10.1107/S1600536805026632

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 10| October 2005| Pages o3161-o3163

doi:10.1107/S1600536805026632

Isonicotinamide–formamide (1/1)

Iain D. H. Oswald,^a ^* W. D. Sam Motherwell ^b and Simon Parsons ^c

^aEuropean Synchrotron Radiation Facility, 6 Rue Jules Horowitz, BP 220, 38043 Grenoble Cedex 9, France, ^bCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England, and ^cSchool of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland
^*Correspondence e-mail: iain.oswald@esrf.fr

(Received 11 July 2005; accepted 19 August 2005; online 7 September 2005)

The 1:1 co-crystal of isonicotinamide and formamide, C₆H₆N₂O·CH₃NO, consists of hydrogen-bonded dimers, each comprising two isonicotinamide or two formamide molecules. These dimers are connected further by hydrogen bonds into sheets, which are parallel to the ( $[\overline{2}]$ 11) plane.

Comment

Isonicotinamide has been shown to crystallize with carboxylic acids in a 1:1 stoichiometry to form a robust building block or `supermolecule', (I), consisting of two amide and two acid molecules (Aakeröy et al., 2002 ; Oswald et al., 2004 ). Amides contain C=O and C—NH₂ groups that could act in an analogous way to the C=O and C—OH groups of carboxylic acids. The aim of the present investigation was to assess the validity of this analogy in the case of the simplest amide, formamide.

The title co-crystal, (II), crystallizes in the monoclinic space group P2₁/c with one molecule of each component in the asymmetric unit (Fig. 1). The bond distances and angles are unremarkable.

Amides characteristically form R₂²(8) (Bernstein et al. 1995 ) centrosymmetric dimers through hydrogen bonding between the NH₂ and C=O groups. This behaviour is observed in (II), where homomeric dimers are formed (i.e. formamide forms a dimer with another formamide etc.), the two components in each case being related by crystallographic inversion centres. The N⋯O distances in the R₂²(8) dimers are 2.9239 (16) Å in the case of isonicotinamide and 2.9696 (16) Å for formamide.

In co-crystals of carboxylic acids with isonicotinamide, homomeric R₂²(8) dimers are often formed between the amide groups of the isonicotinamide molecules (Aakeröy et al., 2002). The two pyridyl functions at either end of the nicotinamide dimer so formed hydrogen bond to two carboxylic acid molecules in R₂²(7) motifs comprising C—OH⋯N and C—H⋯O hydrogen bonds. Of these interactions, only the R₂²(8) dimer formation is observed in (II).

The second donor function of the isonicotinamide forms a hydrogen bond to the carbonyl O atom of the formamide; these interactions build up chains. The chains are linked together through a hydrogen bond between a symmetry-equivalent formamide dimer and the pyridine N atom of the isonicotinamide forming an open grid-like layer parallel to the ( $[\overline{2}]$ 11) plane (Fig. 2). The second donor function of the formamide molecules serves to link this layer with a symmetry equivalent parallel to ( $[\overline{2}]$ $[\overline{1}]$ 1) filling in the structure.

Figure 1
The asymmetric unit of (II). Displacement ellipsoids are shown as 30% probability surfaces and H atoms are drawn as circles of arbitrary radii.

Figure 2
Formation of hydrogen-bonded layers in (II); hydrogen bonds are shown as broken lines. This view is approximately along the ( $[\overline{2}]$ 11) reciprocal lattice direction.

Experimental

Isonicotinamide (0.49 g, 4.02 mmol) was dissolved in an excess of formamide (1.48 g, 32.10 mmol) and warmed until all the solid dissolved. On cooling, long colourless needles were produced, which fractured into thinner shards, degrading the crystal quality, when attempts were made to cut them to a more suitable length.

Crystal data

C₆H₆N₂O·CH₃NO
M_r = 167.17
Monoclinic, P 2₁ /c
a = 10.5785 (18) Å
b = 3.7461 (6) Å
c = 20.002 (3) Å
β = 94.587 (3)°
V = 790.1 (2) Å³
Z = 4
D_x = 1.405 Mg m⁻³
Mo Kα radiation
Cell parameters from 1965 reflections
θ = 2.7–28°
μ = 0.11 mm⁻¹
T = 150 (2) K
Needle, colourless
1.5 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2004 )T_min = 0.663, T_max = 1.000
4454 measured reflections
1860 independent reflections
1554 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 28.7°
h = −13 → 10
k = −4 → 4
l = −23 → 25

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.122
S = 1.06
1860 reflections
125 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0688P)² + 0.1905P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3S—H3S2⋯N1ⁱ	0.92 (2)	2.09 (2)	2.9937 (17)	167 (2)
N3S—H3S1⋯O2Sⁱⁱ	0.95 (2)	2.03 (2)	2.9696 (16)	172 (2)
N9—H91⋯O8ⁱⁱⁱ	0.90 (2)	2.03 (2)	2.9239 (16)	172 (2)
N9—H92⋯O2S	0.89 (2)	2.08 (2)	2.9544 (17)	167 (2)
C5—H5⋯O2S	0.95	2.35	3.2384 (17)	156
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, +z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+3, -z; (iii) -x+1, -y+1, -z.

H atoms attached to C atoms were placed in idealized positions (C—H = 0.95 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.2U_eq(C). H atoms attached to N atoms were located in a difference map and refined freely.

Data collection: SMART (Bruker–Nonius, 2001 ); temperature control: Oxford Cryosystems low-temperature device (Cosier & Glazer, 1986 ); cell refinement: SAINT (Bruker–Nonius, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001 ) and MERCURY (Taylor & Macrae, 2001 ; Bruno et al., 2002 ); software used to prepare material for publication: PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, II. DOI: 10.1107/S1600536805026632/jh6015sup1.cif

Structure factors: contains datablock II. DOI: 10.1107/S1600536805026632/jh6015IIsup2.hkl

Comment top

Isonicotinamide has been shown to crystallize with carboxylic acids in a 1:1 stoichiometry to form a robust building block or `supermolecule', (I), consisting of two amide and two acid molecules (Aakeröy et al., 2002; Oswald et al., 2004). Amides contain C═O and C—NH₂ groups that could act in an analogous way to the C═O and C—OH groups of carboxylic acids. The aim of the present investigation was to assess the validity of this analogy in the case of the simplest amide, formamide.

The title co-crystal, (II), crystallizes in the monoclinic space group P2₁/c with one molecule of each component in the asymmetric unit (Fig. 1). The primary bond distances and angles are unremarkable.

Amides characteristically form R₂²(8) (Bernstein et al. 1995) centrosymmetric dimers through hydrogen bonding between the NH₂ and C═O moieties. This behaviour is observed in (II), where homomeric dimers are formed (i.e. formamide forms a dimer with another formamide etc.), the two components in each case being related by crystallographic inversion centres. The N···O distances in the R₂²(8) dimers are 2.9239 (16) Å in the case of isonicotinamide and 2.9696 (16) Å for formamide.

In co-crystals of carboxylic acids with isonicotinamide, homomeric R₂²(8) dimers are often formed between the amide groups of the isonicotinamide molecules (Aakeröy et al., 2002). The two pyridyl functions at either end of the nicotinamide dimer so formed hydrogen bond to two carboxylic acid molecules in R₂²(7) motifs comprising C—OH···N and C—H···O hydrogen bonds. Of these interactions, only the R₂²(8) dimer formation is observed in (II).

The second donor function of the isonicotinamide forms a hydrogen bond to the carbonyl O atom of the formamide; these interactions build-up chains. The chains are linked together through a hydrogen bond between a symmetry-equivalent formamide dimer and the pyridine N atom of the isonicotinamide forming an open grid-like layer parallel to the (−211) planes (Fig. 2). The second donor function of the formamide molecules serves to link this layer with a symmetry equivalent parallel to (−2–11) filling-in the structure.

Experimental top

Computing details top

Data collection: SMART (Bruker–Nonius, 2001); cell refinement: SAINT (Bruker–Nonius, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001) and Mercury (Taylor & Macrae, 2001; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of (II). Displacement ellipsoids are shown as 30% probability surfaces and H atoms are drawn as circles of arbitrary radii.
	Fig. 2. Formation of hydrogen-bonded layers in (II). This view is approximately along the (−211) reciprocal lattice direction.

isonicotinamide–formamide (1/1) top

Crystal data top

C₆H₆N₂O·CH₃NO	F(000) = 352
M_r = 167.17	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5785 (18) Å	Cell parameters from 1965 reflections
b = 3.7461 (6) Å	θ = 2.7–28°
c = 20.002 (3) Å	µ = 0.11 mm⁻¹
β = 94.587 (3)°	T = 150 K
V = 790.1 (2) Å³	Needle, colourless
Z = 4	1.5 × 0.14 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1860 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 28.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→10
T_min = 0.663, T_max = 1.000	k = −4→4
4454 measured reflections	l = −23→25

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)] = 0.044	Hydrogen site location: geom/difmap
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0688P)² + 0.1905P] where P = (F_o² + 2F_c²)/3
1860 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₆H₆N₂O·CH₃NO	V = 790.1 (2) Å³
M_r = 167.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5785 (18) Å	µ = 0.11 mm⁻¹
b = 3.7461 (6) Å	T = 150 K
c = 20.002 (3) Å	1.5 × 0.14 × 0.08 mm
β = 94.587 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1860 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1554 reflections with I > 2σ(I)
T_min = 0.663, T_max = 1.000	R_int = 0.022
4454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
1860 reflections	Δρ_min = −0.20 e Å⁻³
125 parameters

Special details top

Experimental. The temperature of the sample was controlled using an Oxford Cryosystems low-temperature device (Cosier & Glazer, 1986).

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
N1	0.82075 (11)	0.8957 (4)	0.27104 (6)	0.0264 (3)
C2	0.70122 (14)	0.7803 (4)	0.27066 (7)	0.0271 (3)
H2	0.6668	0.7416	0.3125	0.033*
C3	0.62479 (13)	0.7142 (4)	0.21249 (7)	0.0234 (3)
H3	0.5404	0.6312	0.2149	0.028*
C4	0.67245 (12)	0.7701 (4)	0.15093 (6)	0.0190 (3)
C5	0.79641 (13)	0.8906 (4)	0.15063 (7)	0.0227 (3)
H5	0.8330	0.9331	0.1095	0.027*
C6	0.86592 (13)	0.9480 (4)	0.21147 (7)	0.0253 (3)
H6	0.9508	1.0293	0.2106	0.030*
C7	0.58927 (13)	0.6842 (4)	0.08820 (7)	0.0206 (3)
O8	0.48915 (9)	0.5197 (3)	0.09317 (5)	0.0292 (3)
N9	0.63022 (12)	0.7882 (4)	0.03055 (6)	0.0242 (3)
H91	0.5893 (19)	0.713 (5)	−0.0082 (10)	0.039 (5)*
H92	0.7035 (18)	0.904 (5)	0.0296 (9)	0.036 (5)*
C1S	0.84255 (13)	1.2871 (4)	−0.05370 (7)	0.0242 (3)
H1S	0.7674	1.2035	−0.0779	0.029*
O2S	0.85676 (9)	1.2164 (3)	0.00663 (5)	0.0283 (3)
N3S	0.92304 (12)	1.4691 (4)	−0.08733 (6)	0.0266 (3)
H3S2	0.9045 (17)	1.512 (5)	−0.1325 (10)	0.038 (5)*
H3S1	0.9983 (19)	1.561 (6)	−0.0645 (10)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0260 (6)	0.0316 (7)	0.0207 (6)	0.0011 (5)	−0.0044 (5)	−0.0021 (5)
C2	0.0264 (7)	0.0362 (9)	0.0188 (7)	0.0022 (6)	0.0018 (5)	−0.0009 (6)
C3	0.0190 (6)	0.0296 (8)	0.0217 (7)	−0.0013 (6)	0.0022 (5)	−0.0009 (6)
C4	0.0184 (6)	0.0195 (7)	0.0188 (6)	0.0003 (5)	−0.0011 (5)	−0.0015 (5)
C5	0.0203 (6)	0.0274 (7)	0.0200 (6)	−0.0026 (6)	−0.0007 (5)	0.0020 (6)
C6	0.0198 (6)	0.0296 (8)	0.0256 (7)	−0.0031 (6)	−0.0042 (5)	−0.0002 (6)
C7	0.0182 (6)	0.0236 (7)	0.0197 (6)	−0.0007 (5)	−0.0010 (5)	−0.0040 (5)
O8	0.0228 (5)	0.0414 (7)	0.0231 (5)	−0.0120 (5)	0.0001 (4)	−0.0046 (4)
N9	0.0199 (6)	0.0338 (7)	0.0184 (6)	−0.0064 (5)	−0.0024 (5)	−0.0021 (5)
C1S	0.0209 (7)	0.0285 (8)	0.0226 (7)	−0.0002 (6)	−0.0008 (5)	−0.0004 (6)
O2S	0.0248 (5)	0.0389 (7)	0.0211 (5)	−0.0063 (4)	0.0007 (4)	0.0041 (4)
N3S	0.0259 (6)	0.0350 (7)	0.0184 (6)	−0.0033 (5)	−0.0023 (5)	0.0029 (5)

Geometric parameters (Å, º) top

N1—C6	1.3332 (19)	C6—H6	0.9500
N1—C2	1.3357 (19)	C7—O8	1.2363 (17)
C2—C3	1.3851 (19)	C7—N9	1.3224 (18)
C2—H2	0.9500	N9—H91	0.90 (2)
C3—C4	1.3833 (19)	N9—H92	0.890 (19)
C3—H3	0.9500	C1S—O2S	1.2328 (17)
C4—C5	1.3873 (18)	C1S—N3S	1.3167 (19)
C4—C7	1.5086 (17)	C1S—H1S	0.9500
C5—C6	1.3873 (18)	N3S—H3S2	0.923 (19)
C5—H5	0.9500	N3S—H3S1	0.95 (2)

C6—N1—C2	116.70 (11)	N1—C6—H6	118.0
N1—C2—C3	123.46 (13)	C5—C6—H6	118.0
N1—C2—H2	118.3	O8—C7—N9	124.03 (12)
C3—C2—H2	118.3	O8—C7—C4	119.06 (12)
C4—C3—C2	119.39 (13)	N9—C7—C4	116.90 (12)
C4—C3—H3	120.3	C7—N9—H91	119.3 (13)
C2—C3—H3	120.3	C7—N9—H92	120.6 (12)
C3—C4—C5	117.72 (12)	H91—N9—H92	119.6 (17)
C3—C4—C7	118.57 (12)	O2S—C1S—N3S	125.31 (14)
C5—C4—C7	123.67 (12)	O2S—C1S—H1S	117.3
C4—C5—C6	118.78 (13)	N3S—C1S—H1S	117.3
C4—C5—H5	120.6	C1S—N3S—H3S2	119.7 (12)
C6—C5—H5	120.6	C1S—N3S—H3S1	119.6 (12)
N1—C6—C5	123.95 (13)	H3S2—N3S—H3S1	120.7 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3S—H3S2···N1ⁱ	0.92 (2)	2.09 (2)	2.9937 (17)	167.2 (16)
N3S—H3S1···O2Sⁱⁱ	0.95 (2)	2.03 (2)	2.9696 (16)	172.2 (17)
N9—H91···O8ⁱⁱⁱ	0.90 (2)	2.03 (2)	2.9239 (16)	172.1 (17)
N9—H92···O2S	0.890 (19)	2.08 (2)	2.9544 (17)	167.0 (17)
C5—H5···O2S	0.95	2.35	3.2384 (17)	156

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) −x+2, −y+3, −z; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₆H₆N₂O·CH₃NO
M_r	167.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	10.5785 (18), 3.7461 (6), 20.002 (3)
β (°)	94.587 (3)
V (Å³)	790.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	1.5 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.663, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4454, 1860, 1554
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.06
No. of reflections	1860
No. of parameters	125
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20

Computer programs: SMART (Bruker–Nonius, 2001), SAINT (Bruker–Nonius, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001) and Mercury (Taylor & Macrae, 2001; Bruno et al., 2002), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3S—H3S2···N1ⁱ	0.92 (2)	2.09 (2)	2.9937 (17)	167.2 (16)
N3S—H3S1···O2Sⁱⁱ	0.95 (2)	2.03 (2)	2.9696 (16)	172.2 (17)
N9—H91···O8ⁱⁱⁱ	0.90 (2)	2.03 (2)	2.9239 (16)	172.1 (17)
N9—H92···O2S	0.890 (19)	2.08 (2)	2.9544 (17)	167.0 (17)
C5—H5···O2S	0.95	2.35	3.2384 (17)	156

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) −x+2, −y+3, −z; (iii) −x+1, −y+1, −z.

Acknowledgements

We thank the CCDC, the EPSRC and The University of Edinburgh for funding.

References

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Volume 61| Part 10| October 2005| Pages o3161-o3163

doi:10.1107/S1600536805026632

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Isonicotinamide–formamide (1/1)

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds