Patterns of hydrogen bonding in mono- and di-substituted N-arylpyrazinecarboxamides

The molecular and supramolecular structures of 18 N-arylpyrazinecarboxamides, Ar NHCO(C₄H₃N₂), have been determined, including the stoichiometric monohydrate of N-(3-methoxyphenyl)pyrazinecarboxamide, and two polymorphs of N-(4-fluorophenyl)pyrazinecarboxamide having Z′ values of 1 and 4, respectively. The aryl groups were selected to include the geometric isomers for a compact range of substituents, namely methyl, trifluoromethyl, fluoro, chloro, methoxy and nitro groups, which exhibit markedly varied electronic properties and markedly varied behaviour as hydrogen-bond donors and acceptors. However, not all isomers in each group could be structurally investigated. A small number of derivatives containing disubstituted aryl groups have also been included in this study. The crystal structures of the solvent-free carboxamides reported here exhibit a wide range of direction-specific intermolecular forces, including N—H...N, N—H...O, C—H...N and C—H...O hydrogen bonds, and π...π stacking interactions, while the structure of N-(3-methoxyphenyl)pyrazinecarboxamide monohydrate also contains O—H...N and O—H...O hydrogen bonds. The resulting supramolecular structures can be zero-, one- or two-dimensional, although no three-dimensional supramolecular aggregation has been observed. In the finite, zero-dimensional structures, pairs of molecules are linked by hydrogen bonds to form cyclic centrosymmetric dimers. The one-dimensional structures include chains formed by the π-stacking of otherwise isolated molecules, simple chains generated by either C—H...O or C—H...N hydrogen bonds, and hydrogen-bonded chains of rings. The two-dimensional structures include examples of both π-stacked hydrogen-bonded chains and hydrogen-bonded sheets.

S1. Comment

In full text version

S2. Experimental

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S3. Refinement

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Computing details

Data collection: COLLECT (Hooft, 1999) for (I), (II), (III), (IV), (V), (VII), (Xa), (Xb), (XII), (XIII), (XIV), (XV), (XVII), (XX), (XXI), (XXIII), (XXIV); Bruker APEX2 (Bruker, 2003) for (XXII). Cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT for (I), (II), (III), (IV), (V), (VII), (Xa), (Xb), (XII), (XIII), (XIV), (XV), (XVII), (XX), (XXI), (XXIII), (XXIV); Bruker APEX2 for (XXII). Data reduction: DENZO & COLLECT for (I), (II), (III), (IV), (V), (VII), (Xa), (Xb), (XII), (XIII), (XIV), (XV), (XVII), (XX), (XXI), (XXIII), (XXIV); Bruker SAINT (Bruker, 2001) for (XXII). For all compounds, program(s) used to solve structure: OSCAIL (McArdle, 2003) & SHELXS97 (Sheldrick, 1997). Program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997) for (I), (II), (III), (IV), (V), (VII), (Xa), (Xb), (XII), (XIII), (XIV), (XV), (XVII), (XX), (XXI), (XXIII), (XXIV); OSCAIL & SHELXL97 (Sheldrick, 1997) for (XXII). For all compounds, molecular graphics: PLATON (Spek, 2003). Software used to prepare material for publication: SHELXL97 & PRPKAPPA (Ferguson, 1999) for (I), (II), (III), (IV), (V), (VII), (Xa), (Xb), (XII), (XIII), (XIV), (XV), (XVII), (XX), (XXI), (XXIII), (XXIV); SHELXL97 and PRPKAPPA (Ferguson, 1999) for (XXII).

Figures

In full text version

(I) N-phenylpyrazinecarboxamide

Crystal data

C11H9N3O	Z = 2
Mr = 199.21	F(000) = 208
Triclinic, P1	Dx = 1.440 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9716 (3) Å	Cell parameters from 2101 reflections
b = 7.5270 (4) Å	θ = 2.9–27.6°
c = 11.0318 (6) Å	µ = 0.10 mm^−1
α = 83.295 (3)°	T = 120 K
β = 85.377 (4)°	Plate, colourless
γ = 69.009 (3)°	0.28 × 0.22 × 0.02 mm
V = 459.38 (4) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2101 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1823 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 2.9°
ϕ & ω scans	h = −7→7
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −9→9
Tmin = 0.978, Tmax = 0.998	l = −14→14
7558 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.265P] where P = (Fo^2 + 2Fc^2)/3
2101 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.5006 (2)	0.16240 (18)	0.29628 (11)	0.0230 (3)
C2	0.7005 (3)	0.1647 (2)	0.34092 (12)	0.0211 (3)
C3	0.9175 (3)	0.1167 (2)	0.27407 (13)	0.0238 (3)
N4	0.9394 (2)	0.06413 (19)	0.16051 (11)	0.0259 (3)
C5	0.7395 (3)	0.0611 (2)	0.11629 (13)	0.0240 (3)
C6	0.5219 (3)	0.1100 (2)	0.18288 (13)	0.0249 (3)
C7	0.6915 (3)	0.2221 (2)	0.46763 (13)	0.0219 (3)
O7	0.87125 (19)	0.22883 (16)	0.50993 (9)	0.0275 (3)
N17	0.4728 (2)	0.26343 (18)	0.52595 (10)	0.0228 (3)
C11	0.4057 (3)	0.3224 (2)	0.64507 (12)	0.0212 (3)
C12	0.5712 (3)	0.3144 (2)	0.72918 (13)	0.0235 (3)
C13	0.4907 (3)	0.3697 (2)	0.84524 (13)	0.0249 (3)
C14	0.2487 (3)	0.4347 (2)	0.87815 (13)	0.0272 (3)
C15	0.0846 (3)	0.4438 (2)	0.79329 (14)	0.0279 (3)
C16	0.1616 (3)	0.3876 (2)	0.67748 (13)	0.0248 (3)
H3	1.0546	0.1213	0.3099	0.029*
H5	0.7461	0.0241	0.0363	0.029*
H6	0.3846	0.1061	0.1470	0.030*
H17	0.3475	0.2684	0.4839	0.027*
H12	0.7379	0.2714	0.7074	0.028*
H13	0.6038	0.3629	0.9030	0.030*
H14	0.1954	0.4725	0.9578	0.033*
H15	−0.0822	0.4890	0.8149	0.033*
H16	0.0481	0.3934	0.6202	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0239 (6)	0.0252 (6)	0.0205 (6)	−0.0087 (5)	−0.0006 (5)	−0.0043 (5)
C2	0.0237 (7)	0.0202 (7)	0.0193 (7)	−0.0076 (6)	−0.0011 (5)	−0.0022 (5)
C3	0.0220 (7)	0.0277 (8)	0.0217 (7)	−0.0078 (6)	−0.0019 (5)	−0.0047 (6)
N4	0.0257 (6)	0.0293 (7)	0.0216 (6)	−0.0077 (5)	0.0009 (5)	−0.0054 (5)
C5	0.0290 (8)	0.0251 (7)	0.0181 (7)	−0.0086 (6)	−0.0013 (6)	−0.0050 (5)
C6	0.0258 (7)	0.0288 (8)	0.0218 (7)	−0.0106 (6)	−0.0019 (6)	−0.0048 (6)
C7	0.0247 (7)	0.0211 (7)	0.0200 (7)	−0.0080 (6)	−0.0011 (5)	−0.0032 (5)
O7	0.0252 (6)	0.0365 (6)	0.0239 (5)	−0.0127 (5)	−0.0010 (4)	−0.0085 (4)
N17	0.0230 (6)	0.0293 (7)	0.0185 (6)	−0.0106 (5)	−0.0007 (5)	−0.0066 (5)
C11	0.0262 (7)	0.0209 (7)	0.0177 (6)	−0.0100 (6)	0.0016 (5)	−0.0035 (5)
C12	0.0224 (7)	0.0262 (7)	0.0221 (7)	−0.0084 (6)	−0.0007 (5)	−0.0034 (5)
C13	0.0289 (8)	0.0291 (8)	0.0193 (7)	−0.0129 (6)	−0.0035 (6)	−0.0025 (6)
C14	0.0308 (8)	0.0346 (9)	0.0202 (7)	−0.0155 (7)	0.0047 (6)	−0.0094 (6)
C15	0.0236 (7)	0.0353 (8)	0.0272 (8)	−0.0125 (6)	0.0040 (6)	−0.0088 (6)
C16	0.0249 (7)	0.0305 (8)	0.0227 (7)	−0.0135 (6)	−0.0014 (6)	−0.0052 (6)

Geometric parameters (Å, º)

N1—C2	1.3342 (18)	N17—H17	0.90
N1—C6	1.3382 (18)	C11—C12	1.391 (2)
C2—C3	1.388 (2)	C11—C16	1.392 (2)
C2—C7	1.5020 (19)	C12—C13	1.388 (2)
C3—N4	1.3401 (18)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.382 (2)
N4—C5	1.3342 (19)	C13—H13	0.95
C5—C6	1.389 (2)	C14—C15	1.388 (2)
C5—H5	0.95	C14—H14	0.95
C6—H6	0.95	C15—C16	1.384 (2)
C7—O7	1.2238 (17)	C15—H15	0.95
C7—N17	1.3552 (18)	C16—H16	0.95
N17—C11	1.4174 (17)
C2—N1—C6	115.88 (12)	C11—N17—H17	113.1
N1—C2—C3	122.30 (13)	C12—C11—C16	119.84 (13)
N1—C2—C7	119.17 (12)	C12—C11—N17	123.08 (13)
C3—C2—C7	118.53 (12)	C16—C11—N17	117.07 (12)
N4—C3—C2	121.93 (13)	C13—C12—C11	119.43 (13)
N4—C3—H3	119.0	C13—C12—H12	120.3
C2—C3—H3	119.0	C11—C12—H12	120.3
C5—N4—C3	115.66 (12)	C14—C13—C12	121.10 (13)
N4—C5—C6	122.47 (13)	C14—C13—H13	119.5
N4—C5—H5	118.8	C12—C13—H13	119.5
C6—C5—H5	118.8	C13—C14—C15	119.10 (13)
N1—C6—C5	121.77 (13)	C13—C14—H14	120.5
N1—C6—H6	119.1	C15—C14—H14	120.5
C5—C6—H6	119.1	C16—C15—C14	120.61 (14)
O7—C7—N17	125.47 (13)	C16—C15—H15	119.7
O7—C7—C2	120.49 (13)	C14—C15—H15	119.7
N17—C7—C2	114.04 (12)	C15—C16—C11	119.92 (13)
C7—N17—C11	127.79 (12)	C15—C16—H16	120.0
C7—N17—H17	118.7	C11—C16—H16	120.0
C6—N1—C2—C3	0.3 (2)	O7—C7—N17—C11	0.2 (2)
C6—N1—C2—C7	179.97 (12)	C2—C7—N17—C11	−179.67 (12)
N1—C2—C3—N4	−0.3 (2)	C7—N17—C11—C12	−11.7 (2)
C7—C2—C3—N4	179.99 (13)	C7—N17—C11—C16	169.43 (14)
C2—C3—N4—C5	0.0 (2)	C16—C11—C12—C13	0.7 (2)
C3—N4—C5—C6	0.3 (2)	N17—C11—C12—C13	−178.12 (13)
C2—N1—C6—C5	0.0 (2)	C11—C12—C13—C14	−0.7 (2)
N4—C5—C6—N1	−0.3 (2)	C12—C13—C14—C15	0.2 (2)
N1—C2—C7—O7	−178.65 (13)	C13—C14—C15—C16	0.4 (2)
C3—C2—C7—O7	1.1 (2)	C14—C15—C16—C11	−0.4 (2)
N1—C2—C7—N17	1.23 (19)	C12—C11—C16—C15	−0.1 (2)
C3—C2—C7—N17	−179.06 (13)	N17—C11—C16—C15	178.76 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.90	2.31	2.7050 (17)	107
C16—H16···O7^i	0.95	2.37	3.220 (2)	148

Symmetry code: (i) x−1, y, z.

(II) N-(2-methylphenyl)pyrazinecarboxamide

Crystal data

C12H11N3O	F(000) = 896
Mr = 213.24	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4787 reflections
a = 15.5361 (9) Å	θ = 1.3–27.7°
b = 7.0360 (3) Å	µ = 0.09 mm^−1
c = 18.9863 (9) Å	T = 120 K
β = 91.307 (2)°	Needle, colourless
V = 2074.89 (18) Å^3	0.52 × 0.04 × 0.02 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	4787 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2575 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.112
Detector resolution: 9.091 pixels mm^-1	θmax = 27.7°, θmin = 1.3°
ϕ & ω scans	h = −20→20
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −9→9
Tmin = 0.965, Tmax = 0.998	l = −24→24
25597 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.110	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 1.5066P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4787 reflections	Δρmax = 0.26 e Å^−3
292 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.83793 (16)	0.0329 (3)	0.31019 (12)	0.0204 (6)
C12	0.9076 (2)	0.0821 (4)	0.34852 (14)	0.0191 (7)
C13	0.9032 (2)	0.1184 (4)	0.42009 (15)	0.0246 (8)
N14	0.82955 (17)	0.1107 (4)	0.45482 (12)	0.0277 (7)
C15	0.7601 (2)	0.0640 (4)	0.41596 (16)	0.0271 (8)
C16	0.7640 (2)	0.0235 (4)	0.34457 (15)	0.0251 (8)
C17	0.9913 (2)	0.1001 (4)	0.31161 (15)	0.0205 (7)
O17	1.05709 (13)	0.1562 (3)	0.34226 (10)	0.0281 (5)
N117	0.98525 (16)	0.0538 (3)	0.24246 (11)	0.0215 (6)
C111	1.0502 (2)	0.0652 (4)	0.19126 (15)	0.0192 (7)
C112	1.0244 (2)	0.1108 (4)	0.12246 (15)	0.0218 (7)
C121	0.9317 (2)	0.1491 (5)	0.10335 (15)	0.0300 (8)
C113	1.0890 (2)	0.1210 (4)	0.07206 (15)	0.0250 (8)
C114	1.1745 (2)	0.0882 (4)	0.08955 (16)	0.0281 (8)
C115	1.1980 (2)	0.0425 (4)	0.15828 (17)	0.0301 (8)
C116	1.1358 (2)	0.0297 (4)	0.20884 (15)	0.0240 (8)
N21	0.33630 (16)	0.2566 (3)	0.30554 (12)	0.0219 (6)
C22	0.40443 (19)	0.2092 (4)	0.34631 (15)	0.0179 (7)
C23	0.3972 (2)	0.1720 (4)	0.41758 (15)	0.0242 (8)
N24	0.32188 (17)	0.1771 (4)	0.44977 (12)	0.0275 (7)
C25	0.2539 (2)	0.2192 (4)	0.40869 (15)	0.0263 (8)
C26	0.2608 (2)	0.2615 (4)	0.33766 (15)	0.0232 (7)
C27	0.4905 (2)	0.1945 (4)	0.31178 (15)	0.0215 (7)
O27	0.55554 (14)	0.1472 (3)	0.34533 (10)	0.0314 (6)
N217	0.48648 (16)	0.2343 (3)	0.24213 (12)	0.0223 (6)
C211	0.5530 (2)	0.2251 (4)	0.19275 (15)	0.0205 (7)
C212	0.5301 (2)	0.1892 (4)	0.12216 (15)	0.0225 (7)
C221	0.4375 (2)	0.1567 (5)	0.10056 (15)	0.0314 (8)
C213	0.5949 (2)	0.1850 (4)	0.07342 (16)	0.0306 (8)
C214	0.6805 (2)	0.2121 (4)	0.09314 (17)	0.0321 (8)
C215	0.7018 (2)	0.2465 (4)	0.16324 (17)	0.0298 (8)
C216	0.6384 (2)	0.2545 (4)	0.21270 (16)	0.0235 (8)
H13	0.9546	0.1500	0.4454	0.030*
H15	0.7059	0.0583	0.4380	0.032*
H16	0.7128	−0.0117	0.3195	0.030*
H117	0.9339	0.0112	0.2300	0.026*
H12A	0.9262	0.1761	0.0528	0.045*
H12B	0.9115	0.2587	0.1301	0.045*
H12C	0.8970	0.0373	0.1146	0.045*
H113	1.0734	0.1514	0.0247	0.030*
H114	1.2171	0.0970	0.0546	0.034*
H115	1.2567	0.0201	0.1706	0.036*
H116	1.1517	−0.0036	0.2558	0.029*
H23	0.4477	0.1417	0.4445	0.029*
H25	0.1984	0.2203	0.4288	0.032*
H26	0.2105	0.2950	0.3112	0.028*
H217	0.4343	0.2575	0.2253	0.027*
H22A	0.4039	0.2715	0.1101	0.047*
H22B	0.4144	0.0500	0.1274	0.047*
H22C	0.4337	0.1274	0.0501	0.047*
H213	0.5804	0.1629	0.0252	0.037*
H214	0.7241	0.2072	0.0589	0.039*
H215	0.7603	0.2646	0.1772	0.036*
H216	0.6533	0.2802	0.2606	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0213 (16)	0.0205 (15)	0.0193 (13)	−0.0006 (12)	−0.0008 (12)	0.0019 (11)
C12	0.0206 (18)	0.0172 (17)	0.0193 (16)	0.0012 (13)	−0.0011 (14)	−0.0014 (12)
C13	0.024 (2)	0.0255 (19)	0.0238 (17)	−0.0017 (15)	0.0001 (15)	−0.0025 (14)
N14	0.0306 (18)	0.0287 (17)	0.0239 (14)	−0.0032 (13)	0.0038 (13)	−0.0030 (12)
C15	0.027 (2)	0.0248 (19)	0.0300 (18)	−0.0037 (15)	0.0058 (15)	0.0027 (15)
C16	0.0198 (19)	0.0279 (19)	0.0275 (18)	−0.0029 (14)	−0.0005 (15)	0.0012 (14)
C17	0.0218 (19)	0.0191 (17)	0.0205 (16)	0.0022 (14)	−0.0020 (14)	0.0001 (13)
O17	0.0217 (13)	0.0376 (14)	0.0249 (12)	−0.0005 (11)	−0.0008 (10)	−0.0051 (10)
N117	0.0189 (15)	0.0276 (15)	0.0182 (13)	−0.0062 (12)	0.0026 (12)	0.0012 (11)
C111	0.0232 (19)	0.0130 (16)	0.0216 (16)	−0.0013 (13)	0.0030 (14)	−0.0011 (13)
C112	0.0227 (19)	0.0205 (18)	0.0222 (16)	−0.0009 (14)	0.0011 (14)	0.0002 (13)
C121	0.032 (2)	0.036 (2)	0.0221 (17)	0.0019 (16)	−0.0021 (15)	0.0036 (15)
C113	0.030 (2)	0.0248 (19)	0.0205 (16)	0.0030 (15)	0.0052 (15)	0.0032 (14)
C114	0.029 (2)	0.0251 (19)	0.0308 (18)	−0.0025 (15)	0.0129 (15)	−0.0018 (15)
C115	0.025 (2)	0.026 (2)	0.039 (2)	−0.0008 (15)	0.0046 (17)	−0.0033 (15)
C116	0.025 (2)	0.0218 (19)	0.0250 (17)	0.0011 (14)	0.0020 (15)	0.0000 (14)
N21	0.0193 (15)	0.0224 (15)	0.0238 (13)	0.0014 (12)	−0.0016 (12)	−0.0019 (11)
C22	0.0171 (17)	0.0132 (16)	0.0234 (16)	−0.0014 (13)	−0.0012 (13)	−0.0035 (12)
C23	0.0231 (19)	0.0260 (19)	0.0234 (17)	−0.0021 (15)	−0.0005 (15)	0.0002 (14)
N24	0.0267 (17)	0.0299 (16)	0.0259 (15)	−0.0032 (13)	0.0031 (13)	−0.0007 (12)
C25	0.0227 (19)	0.0247 (19)	0.0317 (19)	−0.0027 (14)	0.0068 (15)	−0.0048 (14)
C26	0.0216 (18)	0.0222 (18)	0.0256 (17)	0.0003 (14)	0.0013 (14)	−0.0025 (14)
C27	0.0244 (19)	0.0180 (18)	0.0222 (16)	−0.0016 (14)	−0.0012 (15)	0.0014 (13)
O27	0.0213 (13)	0.0442 (15)	0.0284 (12)	0.0019 (11)	−0.0036 (10)	0.0064 (11)
N217	0.0191 (15)	0.0271 (15)	0.0208 (14)	0.0007 (11)	0.0007 (12)	0.0024 (11)
C211	0.0202 (18)	0.0185 (17)	0.0232 (16)	0.0021 (14)	0.0055 (14)	0.0005 (13)
C212	0.0252 (19)	0.0162 (17)	0.0262 (17)	0.0016 (14)	0.0027 (15)	0.0018 (13)
C221	0.035 (2)	0.036 (2)	0.0228 (17)	0.0001 (16)	−0.0003 (15)	−0.0007 (15)
C213	0.045 (2)	0.0238 (19)	0.0231 (17)	0.0025 (17)	0.0061 (17)	−0.0005 (14)
C214	0.029 (2)	0.028 (2)	0.040 (2)	0.0071 (16)	0.0159 (17)	0.0038 (16)
C215	0.022 (2)	0.029 (2)	0.039 (2)	0.0017 (15)	0.0107 (16)	0.0038 (16)
C216	0.0214 (19)	0.0203 (18)	0.0286 (18)	0.0016 (14)	−0.0009 (15)	0.0001 (14)

Geometric parameters (Å, º)

N11—C16	1.335 (4)	N21—C26	1.334 (4)
N11—C12	1.336 (3)	N21—C22	1.339 (3)
C12—C13	1.386 (4)	C22—C23	1.385 (4)
C12—C17	1.496 (4)	C22—C27	1.506 (4)
C13—N14	1.334 (4)	C23—N24	1.333 (4)
C13—H13	0.95	C23—H23	0.95
N14—C15	1.334 (4)	N24—C25	1.332 (4)
C15—C16	1.388 (4)	C25—C26	1.388 (4)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.230 (3)	C27—O27	1.228 (3)
C17—N117	1.354 (3)	C27—N217	1.352 (3)
N117—C111	1.419 (4)	N217—C211	1.413 (4)
N117—H117	0.88	N217—H217	0.88
C111—C116	1.387 (4)	C211—C216	1.388 (4)
C111—C112	1.394 (4)	C211—C212	1.401 (4)
C112—C113	1.404 (4)	C212—C213	1.383 (4)
C112—C121	1.501 (4)	C212—C221	1.506 (4)
C121—H12A	0.98	C221—H22A	0.98
C121—H12B	0.98	C221—H22B	0.98
C121—H12C	0.98	C221—H22C	0.98
C113—C114	1.382 (4)	C213—C214	1.386 (4)
C113—H113	0.95	C213—H213	0.95
C114—C115	1.385 (4)	C214—C215	1.385 (4)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.380 (4)	C215—C216	1.377 (4)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
C16—N11—C12	116.2 (3)	C26—N21—C22	115.7 (3)
N11—C12—C13	121.6 (3)	N21—C22—C23	122.1 (3)
N11—C12—C17	117.9 (3)	N21—C22—C27	117.6 (3)
C13—C12—C17	120.5 (3)	C23—C22—C27	120.3 (3)
N14—C13—C12	122.7 (3)	N24—C23—C22	122.3 (3)
N14—C13—H13	118.7	N24—C23—H23	118.9
C12—C13—H13	118.7	C22—C23—H23	118.9
C15—N14—C13	115.3 (3)	C25—N24—C23	115.5 (3)
N14—C15—C16	122.6 (3)	N24—C25—C26	122.6 (3)
N14—C15—H15	118.7	N24—C25—H25	118.7
C16—C15—H15	118.7	C26—C25—H25	118.7
N11—C16—C15	121.6 (3)	N21—C26—C25	121.8 (3)
N11—C16—H16	119.2	N21—C26—H26	119.1
C15—C16—H16	119.2	C25—C26—H26	119.1
O17—C17—N117	125.0 (3)	O27—C27—N217	125.6 (3)
O17—C17—C12	121.8 (3)	O27—C27—C22	121.4 (3)
N117—C17—C12	113.1 (3)	N217—C27—C22	113.0 (3)
C17—N117—C111	128.1 (3)	C27—N217—C211	128.4 (3)
C17—N117—H117	112.6	C27—N217—H217	114.5
C111—N117—H117	119.4	C211—N217—H217	116.7
C116—C111—C112	121.3 (3)	C216—C211—C212	120.5 (3)
C116—C111—N117	121.2 (3)	C216—C211—N217	121.5 (3)
C112—C111—N117	117.5 (3)	C212—C211—N217	118.0 (3)
C111—C112—C113	117.2 (3)	C213—C212—C211	118.1 (3)
C111—C112—C121	121.4 (3)	C213—C212—C221	121.4 (3)
C113—C112—C121	121.5 (3)	C211—C212—C221	120.5 (3)
C112—C121—H12A	109.5	C212—C221—H22A	109.5
C112—C121—H12B	109.5	C212—C221—H22B	109.5
H12A—C121—H12B	109.5	H22A—C221—H22B	109.5
C112—C121—H12C	109.5	C212—C221—H22C	109.5
H12A—C121—H12C	109.5	H22A—C221—H22C	109.5
H12B—C121—H12C	109.5	H22B—C221—H22C	109.5
C114—C113—C112	121.7 (3)	C212—C213—C214	121.6 (3)
C114—C113—H113	119.1	C212—C213—H213	119.2
C112—C113—H113	119.1	C214—C213—H213	119.2
C113—C114—C115	119.8 (3)	C215—C214—C213	119.3 (3)
C113—C114—H114	120.1	C215—C214—H214	120.3
C115—C114—H114	120.1	C213—C214—H214	120.3
C116—C115—C114	119.8 (3)	C216—C215—C214	120.2 (3)
C116—C115—H115	120.1	C216—C215—H215	119.9
C114—C115—H115	120.1	C214—C215—H215	119.9
C115—C116—C111	120.2 (3)	C215—C216—C211	120.1 (3)
C115—C116—H116	119.9	C215—C216—H216	119.9
C111—C116—H116	119.9	C211—C216—H216	119.9
C16—N11—C12—C13	0.9 (4)	C26—N21—C22—C23	−1.4 (4)
C16—N11—C12—C17	−178.2 (3)	C26—N21—C22—C27	177.8 (2)
N11—C12—C13—N14	−1.5 (5)	N21—C22—C23—N24	1.4 (5)
C17—C12—C13—N14	177.6 (3)	C27—C22—C23—N24	−177.7 (3)
C12—C13—N14—C15	0.5 (4)	C22—C23—N24—C25	0.4 (4)
C13—N14—C15—C16	0.9 (4)	C23—N24—C25—C26	−2.2 (4)
C12—N11—C16—C15	0.4 (4)	C22—N21—C26—C25	−0.3 (4)
N14—C15—C16—N11	−1.4 (5)	N24—C25—C26—N21	2.2 (5)
N11—C12—C17—O17	175.4 (3)	N21—C22—C27—O27	−178.2 (3)
C13—C12—C17—O17	−3.7 (4)	C23—C22—C27—O27	1.0 (4)
N11—C12—C17—N117	−2.9 (4)	N21—C22—C27—N217	0.5 (4)
C13—C12—C17—N117	178.0 (3)	C23—C22—C27—N217	179.7 (3)
O17—C17—N117—C111	−2.2 (5)	O27—C27—N217—C211	2.3 (5)
C12—C17—N117—C111	176.0 (3)	C22—C27—N217—C211	−176.4 (3)
C17—N117—C111—C116	34.7 (4)	C27—N217—C211—C216	−29.2 (4)
C17—N117—C111—C112	−146.2 (3)	C27—N217—C211—C212	152.1 (3)
C116—C111—C112—C113	−0.7 (4)	C216—C211—C212—C213	−0.3 (4)
N117—C111—C112—C113	−179.8 (3)	N217—C211—C212—C213	178.4 (3)
C116—C111—C112—C121	179.9 (3)	C216—C211—C212—C221	179.8 (3)
N117—C111—C112—C121	0.8 (4)	N217—C211—C212—C221	−1.6 (4)
C111—C112—C113—C114	−0.2 (4)	C211—C212—C213—C214	1.0 (5)
C121—C112—C113—C114	179.2 (3)	C221—C212—C213—C214	−179.1 (3)
C112—C113—C114—C115	0.5 (5)	C212—C213—C214—C215	−0.7 (5)
C113—C114—C115—C116	0.1 (5)	C213—C214—C215—C216	−0.3 (5)
C114—C115—C116—C111	−1.0 (5)	C214—C215—C216—C211	1.0 (5)
C112—C111—C116—C115	1.3 (4)	C212—C211—C216—C215	−0.7 (4)
N117—C111—C116—C115	−179.7 (3)	N217—C211—C216—C215	−179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N117—H117···N11	0.88	2.16	2.655 (3)	115
N217—H217···N21	0.88	2.18	2.654 (3)	113

(III) N-(3-methylphenyl)pyrazinecarboxamide

Crystal data

C12H11N3O	F(000) = 896
Mr = 213.24	Dx = 1.372 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4681 reflections
a = 10.2736 (4) Å	θ = 2.9–27.5°
b = 10.8639 (4) Å	µ = 0.09 mm^−1
c = 18.5040 (5) Å	T = 120 K
β = 90.1970 (19)°	Lath, colourless
V = 2065.24 (12) Å^3	0.28 × 0.10 × 0.06 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	4681 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ & ω scans	h = −13→13
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→13
Tmin = 0.979, Tmax = 0.995	l = −24→23
17301 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 1.1453P] where P = (Fo^2 + 2Fc^2)/3
4681 reflections	(Δ/σ)max = 0.004
291 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.68630 (14)	0.03517 (13)	0.44889 (8)	0.0237 (3)
C12	0.60803 (16)	0.13411 (15)	0.44756 (9)	0.0200 (4)
C13	0.63989 (17)	0.24174 (16)	0.48358 (9)	0.0231 (4)
N14	0.75039 (15)	0.25435 (14)	0.52130 (8)	0.0259 (3)
C15	0.82793 (18)	0.15576 (17)	0.52247 (10)	0.0260 (4)
C16	0.79558 (17)	0.04764 (17)	0.48726 (10)	0.0259 (4)
C17	0.48322 (17)	0.12929 (15)	0.40513 (9)	0.0217 (4)
O17	0.41583 (13)	0.22192 (11)	0.39933 (7)	0.0314 (3)
N117	0.45557 (14)	0.01806 (13)	0.37594 (7)	0.0209 (3)
C111	0.34420 (16)	−0.01176 (15)	0.33402 (9)	0.0201 (4)
C112	0.22540 (17)	0.04723 (16)	0.34415 (9)	0.0221 (4)
C113	0.11700 (17)	0.01228 (16)	0.30384 (10)	0.0245 (4)
C131	−0.01220 (18)	0.0739 (2)	0.31739 (11)	0.0353 (5)
C114	0.13012 (18)	−0.08102 (16)	0.25261 (10)	0.0254 (4)
C115	0.24800 (18)	−0.13969 (16)	0.24276 (10)	0.0254 (4)
C116	0.35547 (17)	−0.10611 (16)	0.28359 (9)	0.0227 (4)
N21	0.65064 (14)	0.53499 (13)	0.45772 (8)	0.0225 (3)
C22	0.72346 (16)	0.63636 (15)	0.46236 (9)	0.0210 (4)
C23	0.69669 (17)	0.74038 (16)	0.42131 (10)	0.0258 (4)
N24	0.59396 (15)	0.74692 (14)	0.37704 (8)	0.0282 (4)
C25	0.52033 (18)	0.64533 (17)	0.37308 (10)	0.0259 (4)
C26	0.54946 (17)	0.53986 (16)	0.41202 (9)	0.0240 (4)
C27	0.83558 (16)	0.64020 (16)	0.51486 (9)	0.0216 (4)
O27	0.89671 (12)	0.73659 (11)	0.52285 (7)	0.0279 (3)
N217	0.85835 (14)	0.53389 (13)	0.55062 (7)	0.0217 (3)
C211	0.95313 (17)	0.51124 (16)	0.60467 (9)	0.0215 (4)
C212	1.05332 (16)	0.59302 (16)	0.62107 (9)	0.0222 (4)
C213	1.14199 (16)	0.56709 (16)	0.67612 (9)	0.0231 (4)
C231	1.24590 (18)	0.65918 (18)	0.69581 (10)	0.0288 (4)
C214	1.13155 (17)	0.45661 (17)	0.71340 (10)	0.0259 (4)
C215	1.03274 (18)	0.37433 (17)	0.69662 (10)	0.0285 (4)
C216	0.94310 (17)	0.40089 (16)	0.64321 (10)	0.0253 (4)
H13	0.5811	0.3091	0.4814	0.028*
H15	0.9079	0.1600	0.5483	0.031*
H16	0.8535	−0.0203	0.4905	0.031*
H117	0.5162	−0.0386	0.3807	0.025*
H112	0.2183	0.1115	0.3787	0.027*
H13A	−0.0804	0.0112	0.3213	0.053*
H13B	−0.0326	0.1295	0.2772	0.053*
H13C	−0.0076	0.1211	0.3625	0.053*
H114	0.0571	−0.1045	0.2241	0.031*
H115	0.2554	−0.2034	0.2078	0.030*
H116	0.4363	−0.1472	0.2772	0.027*
H23	0.7534	0.8092	0.4248	0.031*
H25	0.4457	0.6456	0.3426	0.031*
H26	0.4962	0.4691	0.4061	0.029*
H217	0.8087	0.4712	0.5384	0.026*
H212	1.0613	0.6674	0.5944	0.027*
H43A	1.2431	0.6753	0.7479	0.043*
H43B	1.2307	0.7361	0.6694	0.043*
H43C	1.3315	0.6261	0.6830	0.043*
H214	1.1923	0.4373	0.7505	0.031*
H215	1.0267	0.2988	0.7222	0.034*
H216	0.8749	0.3446	0.6326	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0241 (7)	0.0211 (7)	0.0258 (8)	0.0011 (6)	−0.0035 (6)	−0.0006 (6)
C12	0.0227 (8)	0.0181 (8)	0.0192 (8)	−0.0017 (7)	−0.0001 (7)	0.0022 (7)
C13	0.0259 (9)	0.0183 (8)	0.0250 (9)	−0.0009 (7)	−0.0027 (7)	0.0006 (7)
N14	0.0280 (8)	0.0225 (8)	0.0271 (8)	−0.0032 (6)	−0.0053 (6)	−0.0006 (6)
C15	0.0233 (9)	0.0283 (10)	0.0264 (9)	−0.0031 (7)	−0.0041 (7)	0.0012 (8)
C16	0.0243 (9)	0.0256 (9)	0.0279 (9)	0.0030 (7)	−0.0026 (7)	0.0009 (8)
C17	0.0248 (9)	0.0182 (8)	0.0222 (9)	−0.0005 (7)	−0.0018 (7)	0.0017 (7)
O17	0.0322 (7)	0.0200 (6)	0.0419 (8)	0.0036 (5)	−0.0116 (6)	−0.0027 (6)
N117	0.0210 (7)	0.0185 (7)	0.0231 (7)	0.0003 (6)	−0.0054 (6)	−0.0015 (6)
C111	0.0219 (8)	0.0185 (8)	0.0198 (8)	−0.0024 (7)	−0.0018 (7)	0.0034 (7)
C112	0.0238 (9)	0.0204 (8)	0.0221 (8)	−0.0005 (7)	−0.0006 (7)	−0.0001 (7)
C113	0.0219 (9)	0.0254 (9)	0.0261 (9)	0.0005 (7)	−0.0014 (7)	0.0056 (7)
C131	0.0245 (10)	0.0413 (12)	0.0400 (11)	0.0039 (9)	−0.0027 (8)	−0.0042 (9)
C114	0.0245 (9)	0.0237 (9)	0.0280 (9)	−0.0050 (7)	−0.0068 (7)	0.0019 (8)
C115	0.0306 (9)	0.0193 (9)	0.0262 (9)	−0.0021 (7)	−0.0046 (7)	−0.0019 (7)
C116	0.0243 (9)	0.0194 (8)	0.0244 (9)	−0.0004 (7)	−0.0019 (7)	0.0022 (7)
N21	0.0235 (7)	0.0221 (8)	0.0218 (7)	−0.0006 (6)	−0.0021 (6)	−0.0019 (6)
C22	0.0217 (8)	0.0192 (8)	0.0222 (8)	0.0010 (7)	0.0002 (7)	−0.0043 (7)
C23	0.0263 (9)	0.0200 (9)	0.0311 (10)	−0.0008 (7)	−0.0050 (8)	−0.0016 (8)
N24	0.0290 (8)	0.0247 (8)	0.0308 (9)	0.0026 (6)	−0.0066 (7)	0.0022 (7)
C25	0.0254 (9)	0.0275 (10)	0.0246 (9)	0.0010 (7)	−0.0048 (7)	−0.0017 (8)
C26	0.0247 (9)	0.0227 (9)	0.0245 (9)	−0.0019 (7)	−0.0006 (7)	−0.0028 (7)
C27	0.0230 (9)	0.0196 (8)	0.0223 (9)	0.0017 (7)	−0.0006 (7)	−0.0017 (7)
O27	0.0290 (7)	0.0206 (6)	0.0342 (7)	−0.0022 (5)	−0.0067 (6)	0.0002 (5)
N217	0.0231 (7)	0.0184 (7)	0.0234 (7)	−0.0016 (6)	−0.0056 (6)	−0.0017 (6)
C211	0.0232 (8)	0.0212 (8)	0.0201 (8)	0.0017 (7)	−0.0017 (7)	−0.0036 (7)
C212	0.0229 (8)	0.0218 (9)	0.0220 (9)	0.0018 (7)	0.0006 (7)	−0.0010 (7)
C213	0.0199 (8)	0.0255 (9)	0.0239 (9)	0.0018 (7)	0.0001 (7)	−0.0055 (7)
C231	0.0236 (9)	0.0305 (10)	0.0322 (10)	−0.0014 (8)	−0.0035 (8)	−0.0029 (8)
C214	0.0244 (9)	0.0275 (9)	0.0258 (9)	0.0049 (7)	−0.0066 (7)	−0.0005 (8)
C215	0.0325 (10)	0.0235 (9)	0.0294 (10)	0.0018 (8)	−0.0063 (8)	0.0029 (8)
C216	0.0262 (9)	0.0214 (9)	0.0284 (9)	−0.0024 (7)	−0.0037 (7)	−0.0027 (7)

Geometric parameters (Å, º)

N11—C16	1.333 (2)	N21—C22	1.334 (2)
N11—C12	1.343 (2)	N21—C26	1.339 (2)
C12—C13	1.385 (2)	C22—C23	1.389 (2)
C12—C17	1.502 (2)	C22—C27	1.505 (2)
C13—N14	1.338 (2)	C23—N24	1.336 (2)
C13—H13	0.95	C23—H23	0.95
N14—C15	1.335 (2)	N24—C25	1.340 (2)
C15—C16	1.383 (3)	C25—C26	1.386 (2)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.226 (2)	C27—O27	1.230 (2)
C17—N117	1.353 (2)	C27—N217	1.351 (2)
N117—C111	1.418 (2)	N217—C211	1.415 (2)
N117—H117	0.8801	N217—H217	0.8801
C111—C116	1.391 (2)	C211—C212	1.392 (2)
C111—C112	1.392 (2)	C211—C216	1.399 (2)
C112—C113	1.391 (2)	C212—C213	1.393 (2)
C112—H112	0.95	C212—H212	0.95
C113—C114	1.395 (3)	C213—C214	1.389 (3)
C113—C131	1.509 (2)	C213—C231	1.507 (2)
C131—H13A	0.98	C231—H43A	0.98
C131—H13B	0.98	C231—H43B	0.98
C131—H13C	0.98	C231—H43C	0.98
C114—C115	1.381 (3)	C214—C215	1.387 (3)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.385 (2)	C215—C216	1.379 (3)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
C16—N11—C12	115.57 (15)	C22—N21—C26	116.24 (15)
N11—C12—C13	121.79 (16)	N21—C22—C23	121.78 (16)
N11—C12—C17	119.46 (15)	N21—C22—C27	119.49 (15)
C13—C12—C17	118.75 (15)	C23—C22—C27	118.70 (15)
N14—C13—C12	122.44 (16)	N24—C23—C22	122.24 (16)
N14—C13—H13	118.8	N24—C23—H23	118.9
C12—C13—H13	118.8	C22—C23—H23	118.9
C15—N14—C13	115.57 (15)	C23—N24—C25	115.75 (16)
N14—C15—C16	122.10 (17)	N24—C25—C26	122.13 (17)
N14—C15—H15	119.0	N24—C25—H25	118.9
C16—C15—H15	119.0	C26—C25—H25	118.9
N11—C16—C15	122.53 (17)	N21—C26—C25	121.80 (16)
N11—C16—H16	118.7	N21—C26—H26	119.1
C15—C16—H16	118.7	C25—C26—H26	119.1
O17—C17—N117	125.47 (16)	O27—C27—N217	125.56 (16)
O17—C17—C12	119.86 (15)	O27—C27—C22	119.39 (15)
N117—C17—C12	114.67 (14)	N217—C27—C22	115.05 (15)
C17—N117—C111	126.18 (15)	C27—N217—C211	127.76 (15)
C17—N117—H117	115.9	C27—N217—H217	115.9
C111—N117—H117	117.7	C211—N217—H217	116.3
C116—C111—C112	120.30 (16)	C212—C211—C216	119.44 (16)
C116—C111—N117	117.81 (15)	C212—C211—N217	123.33 (16)
C112—C111—N117	121.84 (15)	C216—C211—N217	117.24 (15)
C113—C112—C111	120.19 (16)	C211—C212—C213	120.75 (16)
C113—C112—H112	119.9	C211—C212—H212	119.6
C111—C112—H112	119.9	C213—C212—H212	119.6
C112—C113—C114	118.93 (16)	C214—C213—C212	119.12 (16)
C112—C113—C131	119.53 (16)	C214—C213—C231	120.64 (16)
C114—C113—C131	121.52 (17)	C212—C213—C231	120.23 (16)
C113—C131—H13A	109.5	C213—C231—H43A	109.5
C113—C131—H13B	109.5	C213—C231—H43B	109.5
H13A—C131—H13B	109.5	H43A—C231—H43B	109.5
C113—C131—H13C	109.5	C213—C231—H43C	109.5
H13A—C131—H13C	109.5	H43A—C231—H43C	109.5
H13B—C131—H13C	109.5	H43B—C231—H43C	109.5
C115—C114—C113	120.79 (17)	C215—C214—C213	120.23 (17)
C115—C114—H114	119.6	C215—C214—H214	119.9
C113—C114—H114	119.6	C213—C214—H214	119.9
C114—C115—C116	120.29 (17)	C216—C215—C214	120.80 (17)
C114—C115—H115	119.9	C216—C215—H215	119.6
C116—C115—H115	119.9	C214—C215—H215	119.6
C115—C116—C111	119.47 (16)	C215—C216—C211	119.64 (17)
C115—C116—H116	120.3	C215—C216—H216	120.2
C111—C116—H116	120.3	C211—C216—H216	120.2
C16—N11—C12—C13	0.3 (2)	C26—N21—C22—C23	−0.8 (2)
C16—N11—C12—C17	179.41 (15)	C26—N21—C22—C27	177.40 (14)
N11—C12—C13—N14	0.5 (3)	N21—C22—C23—N24	2.7 (3)
C17—C12—C13—N14	−178.61 (15)	C27—C22—C23—N24	−175.59 (16)
C12—C13—N14—C15	−0.5 (2)	C22—C23—N24—C25	−1.9 (3)
C13—N14—C15—C16	−0.3 (2)	C23—N24—C25—C26	−0.5 (3)
C12—N11—C16—C15	−1.1 (2)	C22—N21—C26—C25	−1.5 (2)
N14—C15—C16—N11	1.2 (3)	N24—C25—C26—N21	2.3 (3)
N11—C12—C17—O17	−174.75 (16)	N21—C22—C27—O27	−174.76 (15)
C13—C12—C17—O17	4.4 (2)	C23—C22—C27—O27	3.5 (2)
N11—C12—C17—N117	5.2 (2)	N21—C22—C27—N217	4.2 (2)
C13—C12—C17—N117	−175.58 (15)	C23—C22—C27—N217	−177.53 (15)
O17—C17—N117—C111	−0.4 (3)	O27—C27—N217—C211	1.3 (3)
C12—C17—N117—C111	179.60 (14)	C22—C27—N217—C211	−177.52 (15)
C17—N117—C111—C116	152.32 (16)	C27—N217—C211—C212	−10.9 (3)
C17—N117—C111—C112	−30.1 (2)	C27—N217—C211—C216	168.62 (16)
C116—C111—C112—C113	0.0 (2)	C216—C211—C212—C213	−1.1 (2)
N117—C111—C112—C113	−177.59 (15)	N217—C211—C212—C213	178.40 (15)
C111—C112—C113—C114	−1.0 (3)	C211—C212—C213—C214	1.8 (2)
C111—C112—C113—C131	177.77 (16)	C211—C212—C213—C231	−176.94 (16)
C112—C113—C114—C115	1.2 (3)	C212—C213—C214—C215	−1.0 (3)
C131—C113—C114—C115	−177.57 (17)	C231—C213—C214—C215	177.69 (16)
C113—C114—C115—C116	−0.3 (3)	C213—C214—C215—C216	−0.4 (3)
C114—C115—C116—C111	−0.8 (3)	C214—C215—C216—C211	1.0 (3)
C112—C111—C116—C115	1.0 (2)	C212—C211—C216—C215	−0.3 (3)
N117—C111—C116—C115	178.59 (15)	N217—C211—C216—C215	−179.83 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N117—H117···N11	0.88	2.30	2.730 (2)	110
N217—H217···N21	0.88	2.31	2.736 (2)	110
N117—H117···N24^i	0.88	2.46	3.271 (2)	153
N217—H217···N14	0.88	2.45	3.278 (2)	157
C23—H23···N11^ii	0.95	2.59	3.245 (2)	126
C216—H216···N14	0.95	2.61	3.393 (2)	140

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

(IV) N-(4-methylphenyl)pyrazinecarboxamide

Crystal data

C12H11N3O	F(000) = 448
Mr = 213.24	Dx = 1.359 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2386 reflections
a = 14.0039 (3) Å	θ = 3.9–27.5°
b = 5.6916 (2) Å	µ = 0.09 mm^−1
c = 13.3466 (3) Å	T = 120 K
β = 101.6381 (12)°	Block, colourless
V = 1041.92 (5) Å^3	0.45 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2386 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.9°
ϕ & ω scans	h = −18→17
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −7→7
Tmin = 0.963, Tmax = 0.982	l = −17→17
16571 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.072P)^2 + 0.2478P] where P = (Fo^2 + 2Fc^2)/3
2386 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.10417 (7)	0.70553 (17)	0.53519 (7)	0.0263 (2)
C2	0.14400 (7)	0.91597 (18)	0.52930 (8)	0.0196 (2)
C3	0.13099 (9)	1.0986 (2)	0.59390 (9)	0.0269 (3)
N4	0.07704 (8)	1.07444 (18)	0.66559 (8)	0.0298 (3)
C5	0.03669 (8)	0.8640 (2)	0.67077 (8)	0.0229 (3)
C6	0.05016 (9)	0.6816 (2)	0.60661 (9)	0.0277 (3)
C7	0.20361 (8)	0.95957 (19)	0.44903 (8)	0.0223 (2)
O7	0.23117 (7)	1.15898 (15)	0.43456 (7)	0.0337 (2)
N17	0.22250 (7)	0.76557 (17)	0.39810 (7)	0.0231 (2)
C11	0.27918 (8)	0.7565 (2)	0.32058 (8)	0.0210 (2)
C12	0.28028 (9)	0.9393 (2)	0.25186 (8)	0.0270 (3)
C13	0.33448 (9)	0.9161 (2)	0.17559 (9)	0.0281 (3)
C14	0.38804 (8)	0.7148 (2)	0.16622 (8)	0.0237 (3)
C141	0.44564 (9)	0.6869 (2)	0.08284 (9)	0.0321 (3)
C15	0.38622 (9)	0.5349 (2)	0.23624 (9)	0.0277 (3)
C16	0.33239 (9)	0.5541 (2)	0.31276 (9)	0.0270 (3)
H3	0.1613	1.2456	0.5872	0.032*
H5	−0.0026	0.8385	0.7201	0.028*
H6	0.0201	0.5345	0.6135	0.033*
H17	0.1997	0.6205	0.4219	0.028*
H12	0.2444	1.0790	0.2568	0.032*
H13	0.3348	1.0415	0.1287	0.034*
H14A	0.4108	0.5811	0.0299	0.048*
H14B	0.5099	0.6207	0.1119	0.048*
H14C	0.4537	0.8406	0.0525	0.048*
H15	0.4226	0.3957	0.2317	0.033*
H16	0.3321	0.4287	0.3597	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0356 (5)	0.0212 (5)	0.0270 (5)	−0.0051 (4)	0.0181 (4)	−0.0037 (4)
C2	0.0219 (5)	0.0196 (5)	0.0189 (5)	0.0004 (4)	0.0082 (4)	0.0008 (4)
C3	0.0368 (6)	0.0194 (5)	0.0302 (6)	−0.0032 (4)	0.0202 (5)	−0.0019 (4)
N4	0.0429 (6)	0.0216 (5)	0.0319 (5)	−0.0024 (4)	0.0244 (5)	−0.0038 (4)
C5	0.0271 (5)	0.0226 (6)	0.0226 (5)	0.0009 (4)	0.0137 (4)	0.0018 (4)
C6	0.0367 (6)	0.0217 (6)	0.0297 (6)	−0.0056 (5)	0.0191 (5)	−0.0014 (4)
C7	0.0261 (5)	0.0224 (5)	0.0209 (5)	−0.0013 (4)	0.0111 (4)	−0.0008 (4)
O7	0.0509 (5)	0.0224 (4)	0.0367 (5)	−0.0064 (4)	0.0296 (4)	−0.0025 (3)
N17	0.0289 (5)	0.0224 (5)	0.0224 (5)	−0.0022 (4)	0.0154 (4)	−0.0016 (3)
C11	0.0234 (5)	0.0230 (5)	0.0194 (5)	−0.0029 (4)	0.0108 (4)	−0.0033 (4)
C12	0.0366 (6)	0.0246 (6)	0.0228 (6)	0.0063 (5)	0.0134 (5)	0.0014 (4)
C13	0.0402 (7)	0.0268 (6)	0.0210 (5)	0.0006 (5)	0.0150 (5)	0.0025 (4)
C14	0.0234 (5)	0.0298 (6)	0.0202 (5)	−0.0030 (4)	0.0100 (4)	−0.0041 (4)
C141	0.0330 (6)	0.0424 (7)	0.0257 (6)	−0.0007 (5)	0.0169 (5)	−0.0043 (5)
C15	0.0314 (6)	0.0267 (6)	0.0286 (6)	0.0045 (5)	0.0150 (5)	−0.0010 (4)
C16	0.0354 (6)	0.0229 (6)	0.0270 (6)	0.0011 (4)	0.0161 (5)	0.0021 (4)

Geometric parameters (Å, º)

N1—C2	1.3303 (14)	C11—C16	1.3872 (16)
N1—C6	1.3379 (14)	C11—C12	1.3893 (15)
C2—C3	1.3859 (15)	C12—C13	1.3933 (15)
C2—C7	1.5056 (13)	C12—H12	0.95
C3—N4	1.3406 (13)	C13—C14	1.3886 (16)
C3—H3	0.95	C13—H13	0.95
N4—C5	1.3319 (15)	C14—C15	1.3900 (16)
C5—C6	1.3827 (15)	C14—C141	1.5088 (15)
C5—H5	0.95	C141—H14A	0.98
C6—H6	0.95	C141—H14B	0.98
C7—O7	1.2266 (14)	C141—H14C	0.98
C7—N17	1.3505 (14)	C15—C16	1.3907 (15)
N17—C11	1.4264 (13)	C15—H15	0.95
N17—H17	0.96	C16—H16	0.95
C2—N1—C6	115.96 (9)	C12—C11—N17	122.24 (10)
N1—C2—C3	121.96 (10)	C11—C12—C13	119.43 (10)
N1—C2—C7	119.32 (9)	C11—C12—H12	120.3
C3—C2—C7	118.71 (10)	C13—C12—H12	120.3
N4—C3—C2	122.06 (10)	C14—C13—C12	121.86 (10)
N4—C3—H3	119.0	C14—C13—H13	119.1
C2—C3—H3	119.0	C12—C13—H13	119.1
C5—N4—C3	115.81 (9)	C13—C14—C15	117.62 (10)
N4—C5—C6	122.05 (9)	C13—C14—C141	122.16 (10)
N4—C5—H5	119.0	C15—C14—C141	120.21 (10)
C6—C5—H5	119.0	C14—C141—H14A	109.5
N1—C6—C5	122.16 (10)	C14—C141—H14B	109.5
N1—C6—H6	118.9	H14A—C141—H14B	109.5
C5—C6—H6	118.9	C14—C141—H14C	109.5
O7—C7—N17	125.27 (10)	H14A—C141—H14C	109.5
O7—C7—C2	120.12 (9)	H14B—C141—H14C	109.5
N17—C7—C2	114.61 (9)	C14—C15—C16	121.48 (10)
C7—N17—C11	126.09 (9)	C14—C15—H15	119.3
C7—N17—H17	115.1	C16—C15—H15	119.3
C11—N17—H17	118.6	C11—C16—C15	119.96 (10)
C16—C11—C12	119.65 (10)	C11—C16—H16	120.0
C16—C11—N17	118.08 (10)	C15—C16—H16	120.0
C6—N1—C2—C3	0.56 (17)	C2—C7—N17—C11	−178.26 (9)
C6—N1—C2—C7	−178.33 (10)	C7—N17—C11—C16	147.64 (11)
N1—C2—C3—N4	−0.44 (18)	C7—N17—C11—C12	−34.23 (17)
C7—C2—C3—N4	178.45 (10)	C16—C11—C12—C13	0.38 (17)
C2—C3—N4—C5	−0.05 (17)	N17—C11—C12—C13	−177.72 (10)
C3—N4—C5—C6	0.39 (17)	C11—C12—C13—C14	−0.21 (18)
C2—N1—C6—C5	−0.22 (17)	C12—C13—C14—C15	−0.16 (18)
N4—C5—C6—N1	−0.27 (19)	C12—C13—C14—C141	179.04 (11)
N1—C2—C7—O7	171.42 (11)	C13—C14—C15—C16	0.37 (17)
C3—C2—C7—O7	−7.51 (16)	C141—C14—C15—C16	−178.85 (11)
N1—C2—C7—N17	−8.83 (15)	C12—C11—C16—C15	−0.18 (18)
C3—C2—C7—N17	172.24 (10)	N17—C11—C16—C15	178.00 (10)
O7—C7—N17—C11	1.47 (19)	C14—C15—C16—C11	−0.20 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.96	2.26	2.7265 (14)	108
C5—H5···N4^i	0.95	2.51	3.3803 (15)	152
C16—H16···O7^ii	0.95	2.43	3.2617 (15)	146

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

(V) N-(2-trifluoromethylphenyl)pyrazinecarboxamide

Crystal data

C12H8F3N3O	Z = 2
Mr = 267.21	F(000) = 272
Triclinic, P1	Dx = 1.585 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6748 (3) Å	Cell parameters from 2568 reflections
b = 7.8967 (3) Å	θ = 3.4–27.6°
c = 9.8421 (5) Å	µ = 0.14 mm^−1
α = 96.682 (2)°	T = 120 K
β = 103.357 (3)°	Plate, colourless
γ = 101.659 (2)°	0.24 × 0.20 × 0.06 mm
V = 559.99 (4) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2568 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1916 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.4°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −10→10
Tmin = 0.974, Tmax = 0.992	l = −12→12
11305 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 0.1239P] where P = (Fo^2 + 2Fc^2)/3
2568 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.34737 (18)	0.79967 (17)	0.59128 (15)	0.0243 (3)
C2	0.2689 (2)	0.6787 (2)	0.65814 (17)	0.0221 (4)
C3	0.2443 (2)	0.7214 (2)	0.79182 (18)	0.0264 (4)
N4	0.2970 (2)	0.88637 (19)	0.86311 (15)	0.0309 (4)
C5	0.3737 (2)	1.0065 (2)	0.79589 (19)	0.0305 (4)
C6	0.3993 (2)	0.9642 (2)	0.66203 (18)	0.0277 (4)
C7	0.2068 (2)	0.4908 (2)	0.58368 (17)	0.0235 (4)
O7	0.12952 (19)	0.37674 (16)	0.63717 (14)	0.0374 (3)
N17	0.24636 (19)	0.46685 (17)	0.45599 (14)	0.0243 (3)
C11	0.2126 (2)	0.3095 (2)	0.36122 (17)	0.0219 (3)
C12	0.2401 (2)	0.3143 (2)	0.22472 (17)	0.0217 (3)
C121	0.2910 (2)	0.4849 (2)	0.17449 (18)	0.0263 (4)
F121	0.44325 (15)	0.59610 (13)	0.26314 (12)	0.0395 (3)
F122	0.15813 (15)	0.57363 (14)	0.16439 (13)	0.0417 (3)
F123	0.32610 (17)	0.46648 (14)	0.04791 (12)	0.0434 (3)
C13	0.2135 (2)	0.1596 (2)	0.13159 (18)	0.0258 (4)
C14	0.1573 (2)	−0.0021 (2)	0.17053 (19)	0.0277 (4)
C15	0.1266 (2)	−0.0077 (2)	0.30308 (19)	0.0272 (4)
C16	0.1541 (2)	0.1454 (2)	0.39789 (18)	0.0257 (4)
H3	0.1882	0.6308	0.8344	0.032*
H5	0.4121	1.1257	0.8414	0.037*
H6	0.4555	1.0549	0.6196	0.033*
H17	0.3020	0.5730	0.4383	0.029*
H13	0.2339	0.1642	0.0404	0.031*
H14	0.1401	−0.1077	0.1067	0.033*
H15	0.0861	−0.1179	0.3295	0.033*
H16	0.1331	0.1389	0.4888	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0239 (7)	0.0245 (7)	0.0232 (7)	0.0040 (6)	0.0053 (6)	0.0037 (6)
C2	0.0183 (7)	0.0243 (8)	0.0231 (8)	0.0049 (6)	0.0041 (6)	0.0044 (6)
C3	0.0262 (8)	0.0280 (9)	0.0244 (9)	0.0031 (7)	0.0085 (7)	0.0046 (7)
N4	0.0315 (8)	0.0334 (8)	0.0259 (8)	0.0029 (6)	0.0099 (6)	0.0005 (6)
C5	0.0325 (9)	0.0262 (9)	0.0290 (10)	0.0013 (7)	0.0082 (8)	−0.0014 (7)
C6	0.0298 (9)	0.0256 (8)	0.0276 (9)	0.0041 (7)	0.0094 (7)	0.0046 (7)
C7	0.0209 (8)	0.0256 (8)	0.0235 (8)	0.0041 (7)	0.0061 (7)	0.0038 (7)
O7	0.0469 (8)	0.0290 (7)	0.0357 (8)	−0.0044 (6)	0.0231 (6)	0.0012 (5)
N17	0.0320 (8)	0.0187 (7)	0.0221 (7)	0.0030 (6)	0.0095 (6)	0.0037 (5)
C11	0.0217 (8)	0.0234 (8)	0.0214 (8)	0.0062 (6)	0.0061 (6)	0.0043 (6)
C12	0.0209 (8)	0.0214 (8)	0.0228 (8)	0.0046 (6)	0.0057 (6)	0.0050 (6)
C121	0.0318 (9)	0.0254 (8)	0.0238 (9)	0.0064 (7)	0.0108 (7)	0.0060 (7)
F121	0.0409 (6)	0.0314 (6)	0.0390 (6)	−0.0075 (5)	0.0083 (5)	0.0105 (5)
F122	0.0455 (7)	0.0339 (6)	0.0577 (8)	0.0189 (5)	0.0209 (6)	0.0238 (5)
F123	0.0724 (8)	0.0346 (6)	0.0324 (6)	0.0104 (6)	0.0301 (6)	0.0127 (5)
C13	0.0286 (9)	0.0270 (8)	0.0232 (8)	0.0085 (7)	0.0078 (7)	0.0044 (7)
C14	0.0310 (9)	0.0225 (8)	0.0287 (9)	0.0066 (7)	0.0075 (7)	0.0007 (7)
C15	0.0307 (9)	0.0196 (8)	0.0320 (10)	0.0044 (7)	0.0093 (7)	0.0074 (7)
C16	0.0291 (9)	0.0251 (8)	0.0262 (9)	0.0074 (7)	0.0106 (7)	0.0083 (7)

Geometric parameters (Å, º)

N1—C6	1.335 (2)	C11—C16	1.400 (2)
N1—C2	1.344 (2)	C11—C12	1.411 (2)
C2—C3	1.385 (2)	C12—C13	1.388 (2)
C2—C7	1.505 (2)	C12—C121	1.498 (2)
C3—N4	1.340 (2)	C121—F123	1.3319 (19)
C3—H3	0.95	C121—F122	1.342 (2)
N4—C5	1.336 (2)	C121—F121	1.3540 (19)
C5—C6	1.389 (2)	C13—C14	1.390 (2)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—C15	1.382 (2)
C7—O7	1.2161 (19)	C14—H14	0.95
C7—N17	1.361 (2)	C15—C16	1.386 (2)
N17—C11	1.403 (2)	C15—H15	0.95
N17—H17	0.9160	C16—H16	0.95
C6—N1—C2	115.55 (14)	N17—C11—C12	119.73 (14)
N1—C2—C3	122.27 (15)	C13—C12—C11	120.37 (14)
N1—C2—C7	118.10 (14)	C13—C12—C121	118.37 (15)
C3—C2—C7	119.63 (15)	C11—C12—C121	121.22 (14)
N4—C3—C2	122.22 (15)	F123—C121—F122	106.51 (14)
N4—C3—H3	118.9	F123—C121—F121	105.76 (13)
C2—C3—H3	118.9	F122—C121—F121	105.17 (13)
C5—N4—C3	115.35 (15)	F123—C121—C12	113.45 (14)
N4—C5—C6	122.64 (15)	F122—C121—C12	112.39 (13)
N4—C5—H5	118.7	F121—C121—C12	112.91 (14)
C6—C5—H5	118.7	C12—C13—C14	120.64 (16)
N1—C6—C5	121.97 (15)	C12—C13—H13	119.7
N1—C6—H6	119.0	C14—C13—H13	119.7
C5—C6—H6	119.0	C15—C14—C13	119.29 (15)
O7—C7—N17	125.81 (15)	C15—C14—H14	120.4
O7—C7—C2	120.90 (15)	C13—C14—H14	120.4
N17—C7—C2	113.29 (13)	C14—C15—C16	120.85 (15)
C7—N17—C11	128.28 (13)	C14—C15—H15	119.6
C7—N17—H17	109.2	C16—C15—H15	119.6
C11—N17—H17	122.5	C15—C16—C11	120.72 (15)
C16—C11—N17	122.16 (15)	C15—C16—H16	119.6
C16—C11—C12	118.11 (15)	C11—C16—H16	119.6
C6—N1—C2—C3	−0.3 (2)	N17—C11—C12—C13	177.75 (15)
C6—N1—C2—C7	179.83 (14)	C16—C11—C12—C121	176.11 (15)
N1—C2—C3—N4	0.1 (3)	N17—C11—C12—C121	−4.7 (2)
C7—C2—C3—N4	179.95 (15)	C13—C12—C121—F123	−7.5 (2)
C2—C3—N4—C5	0.4 (3)	C11—C12—C121—F123	174.96 (14)
C3—N4—C5—C6	−0.7 (3)	C13—C12—C121—F122	113.44 (17)
C2—N1—C6—C5	0.0 (2)	C11—C12—C121—F122	−64.1 (2)
N4—C5—C6—N1	0.5 (3)	C13—C12—C121—F121	−127.78 (16)
N1—C2—C7—O7	−177.54 (15)	C11—C12—C121—F121	54.6 (2)
C3—C2—C7—O7	2.6 (2)	C11—C12—C13—C14	0.8 (2)
N1—C2—C7—N17	2.4 (2)	C121—C12—C13—C14	−176.82 (15)
C3—C2—C7—N17	−177.45 (14)	C12—C13—C14—C15	0.5 (3)
O7—C7—N17—C11	−1.8 (3)	C13—C14—C15—C16	−1.1 (3)
C2—C7—N17—C11	178.20 (15)	C14—C15—C16—C11	0.4 (3)
C7—N17—C11—C16	−9.8 (3)	N17—C11—C16—C15	−178.32 (15)
C7—N17—C11—C12	171.11 (15)	C12—C11—C16—C15	0.8 (2)
C16—C11—C12—C13	−1.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.92	2.11	2.6770 (19)	119
C15—H15···O7^i	0.95	2.46	3.365 (2)	159

Symmetry code: (i) −x, −y, −z+1.

(VII) N-(4-trifluoromethylphenyl)pyrazinecarboxamide

Crystal data

C12H8F3N3O	Z = 2
Mr = 267.21	F(000) = 272
Triclinic, P1	Dx = 1.637 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8885 (6) Å	Cell parameters from 2499 reflections
b = 7.5257 (9) Å	θ = 1.6–27.6°
c = 13.2762 (16) Å	µ = 0.14 mm^−1
α = 78.349 (7)°	T = 120 K
β = 86.460 (8)°	Plate, colourless
γ = 70.146 (8)°	0.62 × 0.36 × 0.06 mm
V = 541.95 (11) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2499 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1693 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 1.6°
ϕ & ω scans	h = −7→7
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −9→9
Tmin = 0.923, Tmax = 0.991	l = −17→17
11286 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1116P)^2] where P = (Fo^2 + 2Fc^2)/3
2499 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4642 (3)	0.0776 (2)	0.67664 (12)	0.0278 (4)
C2	0.6716 (3)	0.0956 (3)	0.63740 (14)	0.0248 (5)
C3	0.8860 (3)	0.0147 (3)	0.69233 (15)	0.0271 (5)
N4	0.8998 (3)	−0.0863 (2)	0.78857 (12)	0.0298 (4)
C5	0.6928 (3)	−0.1037 (3)	0.82780 (15)	0.0281 (5)
C6	0.4765 (4)	−0.0230 (3)	0.77258 (15)	0.0276 (5)
C7	0.6718 (3)	0.2071 (3)	0.53023 (15)	0.0262 (5)
O7	0.8569 (2)	0.2324 (2)	0.49320 (10)	0.0325 (4)
N17	0.4543 (3)	0.2760 (2)	0.48069 (12)	0.0267 (4)
C11	0.3975 (3)	0.3849 (3)	0.38014 (14)	0.0255 (5)
C12	0.5729 (3)	0.4053 (3)	0.30741 (15)	0.0288 (5)
C13	0.5035 (3)	0.5075 (3)	0.20846 (15)	0.0293 (5)
C14	0.2613 (3)	0.5896 (3)	0.18149 (14)	0.0267 (5)
C141	0.1909 (3)	0.6885 (3)	0.07300 (15)	0.0299 (5)
F141	−0.0373 (2)	0.80723 (19)	0.06405 (9)	0.0435 (4)
F142	0.3306 (2)	0.79080 (18)	0.03048 (9)	0.0410 (4)
F143	0.2095 (2)	0.56168 (19)	0.01173 (9)	0.0421 (4)
C15	0.0874 (3)	0.5709 (3)	0.25408 (15)	0.0284 (5)
C16	0.1548 (4)	0.4684 (3)	0.35307 (15)	0.0292 (5)
H3	1.0286	0.0312	0.6608	0.033*
H5	0.6928	−0.1738	0.8959	0.034*
H6	0.3339	−0.0398	0.8040	0.033*
H17	0.3343	0.2492	0.5157	0.032*
H12	0.7393	0.3495	0.3255	0.035*
H13	0.6230	0.5211	0.1589	0.035*
H15	−0.0789	0.6286	0.2360	0.034*
H16	0.0347	0.4554	0.4024	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0248 (9)	0.0286 (9)	0.0296 (9)	−0.0101 (7)	0.0007 (7)	−0.0028 (7)
C2	0.0260 (10)	0.0217 (10)	0.0277 (11)	−0.0096 (8)	0.0015 (8)	−0.0048 (8)
C3	0.0252 (10)	0.0262 (10)	0.0294 (11)	−0.0097 (8)	0.0012 (8)	−0.0023 (8)
N4	0.0280 (9)	0.0322 (10)	0.0284 (9)	−0.0122 (8)	−0.0016 (7)	−0.0004 (7)
C5	0.0300 (11)	0.0276 (11)	0.0266 (10)	−0.0118 (9)	−0.0005 (8)	−0.0010 (8)
C6	0.0259 (10)	0.0293 (11)	0.0279 (11)	−0.0119 (8)	0.0029 (8)	−0.0022 (8)
C7	0.0272 (10)	0.0231 (10)	0.0289 (11)	−0.0091 (8)	−0.0008 (8)	−0.0047 (8)
O7	0.0277 (8)	0.0387 (9)	0.0313 (8)	−0.0152 (7)	0.0004 (6)	0.0003 (6)
N17	0.0238 (8)	0.0302 (9)	0.0252 (9)	−0.0114 (7)	0.0011 (7)	0.0006 (7)
C11	0.0298 (10)	0.0216 (10)	0.0259 (10)	−0.0100 (8)	−0.0006 (8)	−0.0039 (8)
C12	0.0250 (10)	0.0306 (11)	0.0298 (11)	−0.0091 (9)	0.0001 (8)	−0.0041 (8)
C13	0.0284 (10)	0.0328 (11)	0.0279 (11)	−0.0138 (9)	0.0029 (8)	−0.0034 (8)
C14	0.0296 (11)	0.0215 (10)	0.0286 (11)	−0.0089 (8)	−0.0013 (8)	−0.0030 (8)
C141	0.0276 (11)	0.0312 (11)	0.0294 (11)	−0.0098 (9)	−0.0006 (8)	−0.0027 (8)
F141	0.0307 (7)	0.0497 (8)	0.0347 (7)	0.0000 (6)	−0.0037 (5)	0.0043 (6)
F142	0.0450 (8)	0.0443 (8)	0.0334 (7)	−0.0239 (6)	−0.0019 (6)	0.0093 (6)
F143	0.0556 (9)	0.0420 (8)	0.0295 (7)	−0.0163 (6)	−0.0044 (6)	−0.0073 (6)
C15	0.0234 (10)	0.0291 (11)	0.0322 (11)	−0.0091 (8)	−0.0027 (8)	−0.0035 (8)
C16	0.0274 (10)	0.0319 (11)	0.0297 (11)	−0.0134 (9)	0.0025 (8)	−0.0034 (8)

Geometric parameters (Å, º)

N1—C6	1.336 (3)	C11—C16	1.389 (3)
N1—C2	1.337 (2)	C11—C12	1.395 (3)
C2—C3	1.381 (3)	C12—C13	1.389 (3)
C2—C7	1.499 (3)	C12—H12	0.95
C3—N4	1.340 (2)	C13—C14	1.386 (3)
C3—H3	0.95	C13—H13	0.95
N4—C5	1.333 (2)	C14—C15	1.385 (3)
C5—C6	1.392 (3)	C14—C141	1.494 (3)
C5—H5	0.95	C141—F141	1.334 (2)
C6—H6	0.95	C141—F142	1.336 (2)
C7—O7	1.226 (2)	C141—F143	1.347 (2)
C7—N17	1.363 (2)	C15—C16	1.388 (3)
N17—C11	1.412 (3)	C15—H15	0.95
N17—H17	0.88	C16—H16	0.95
C6—N1—C2	115.89 (17)	C12—C11—N17	123.02 (18)
N1—C2—C3	122.16 (17)	C13—C12—C11	119.79 (19)
N1—C2—C7	118.94 (17)	C13—C12—H12	120.1
C3—C2—C7	118.90 (17)	C11—C12—H12	120.1
N4—C3—C2	122.31 (17)	C14—C13—C12	120.45 (18)
N4—C3—H3	118.8	C14—C13—H13	119.8
C2—C3—H3	118.8	C12—C13—H13	119.8
C5—N4—C3	115.51 (17)	C15—C14—C13	119.68 (18)
N4—C5—C6	122.38 (18)	C15—C14—C141	120.66 (18)
N4—C5—H5	118.8	C13—C14—C141	119.58 (17)
C6—C5—H5	118.8	F141—C141—F142	107.34 (16)
N1—C6—C5	121.75 (18)	F141—C141—F143	105.88 (17)
N1—C6—H6	119.1	F142—C141—F143	105.67 (16)
C5—C6—H6	119.1	F141—C141—C14	112.81 (16)
O7—C7—N17	124.54 (17)	F142—C141—C14	112.92 (17)
O7—C7—C2	120.66 (17)	F143—C141—C14	111.71 (17)
N17—C7—C2	114.80 (16)	C14—C15—C16	120.32 (18)
C7—N17—C11	128.06 (16)	C14—C15—H15	119.8
C7—N17—H17	116.0	C16—C15—H15	119.8
C11—N17—H17	116.0	C15—C16—C11	120.13 (18)
C16—C11—C12	119.63 (18)	C15—C16—H16	119.9
C16—C11—N17	117.31 (17)	C11—C16—H16	119.9
C6—N1—C2—C3	0.3 (3)	C16—C11—C12—C13	−0.5 (3)
C6—N1—C2—C7	−179.80 (17)	N17—C11—C12—C13	177.02 (18)
N1—C2—C3—N4	−0.3 (3)	C11—C12—C13—C14	0.1 (3)
C7—C2—C3—N4	179.78 (18)	C12—C13—C14—C15	0.5 (3)
C2—C3—N4—C5	0.1 (3)	C12—C13—C14—C141	−176.27 (18)
C3—N4—C5—C6	0.2 (3)	C15—C14—C141—F141	21.9 (3)
C2—N1—C6—C5	−0.1 (3)	C13—C14—C141—F141	−161.33 (18)
N4—C5—C6—N1	−0.2 (3)	C15—C14—C141—F142	143.82 (18)
N1—C2—C7—O7	177.35 (18)	C13—C14—C141—F142	−39.4 (3)
C3—C2—C7—O7	−2.7 (3)	C15—C14—C141—F143	−97.2 (2)
N1—C2—C7—N17	−2.1 (3)	C13—C14—C141—F143	79.5 (2)
C3—C2—C7—N17	177.83 (17)	C13—C14—C15—C16	−0.8 (3)
O7—C7—N17—C11	0.6 (3)	C141—C14—C15—C16	175.95 (18)
C2—C7—N17—C11	−179.95 (17)	C14—C15—C16—C11	0.4 (3)
C7—N17—C11—C16	−168.54 (18)	C12—C11—C16—C15	0.2 (3)
C7—N17—C11—C12	13.9 (3)	N17—C11—C16—C15	−177.44 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.29	2.719 (2)	110
C16—H16···O7^i	0.95	2.36	3.174 (2)	143

Symmetry code: (i) x−1, y, z.

(Xa) N-(4-fluorophenyl)pyrazinecarboxamide, P2₁/c polymorph

Crystal data

C11H8FN3O	F(000) = 448
Mr = 217.20	Dx = 1.530 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2161 reflections
a = 11.718 (2) Å	θ = 3.0–27.6°
b = 5.9726 (10) Å	µ = 0.12 mm^−1
c = 13.474 (2) Å	T = 120 K
β = 91.446 (9)°	Needle, colourless
V = 942.7 (3) Å^3	0.46 × 0.09 × 0.04 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2161 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1031 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.0°
ϕ & ω scans	h = −15→15
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −7→7
Tmin = 0.958, Tmax = 0.995	l = −17→17
9806 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.225	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.103P)^2] where P = (Fo^2 + 2Fc^2)/3
2161 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2843 (3)	0.2970 (5)	0.3362 (2)	0.0320 (8)
C2	0.3239 (3)	0.5065 (6)	0.3350 (3)	0.0298 (9)
C3	0.2545 (3)	0.6889 (6)	0.3130 (3)	0.0333 (9)
N4	0.1433 (3)	0.6671 (5)	0.2912 (2)	0.0361 (8)
C5	0.1033 (3)	0.4571 (6)	0.2925 (3)	0.0364 (10)
C6	0.1726 (3)	0.2757 (6)	0.3148 (3)	0.0359 (10)
C7	0.4491 (3)	0.5443 (6)	0.3582 (3)	0.0316 (9)
O7	0.4890 (2)	0.7354 (4)	0.3572 (2)	0.0388 (7)
N17	0.5080 (2)	0.3561 (5)	0.3816 (2)	0.0310 (8)
C11	0.6249 (3)	0.3351 (6)	0.4059 (3)	0.0287 (9)
C12	0.7031 (3)	0.5095 (6)	0.3982 (3)	0.0328 (9)
C13	0.8172 (3)	0.4743 (6)	0.4218 (3)	0.0345 (9)
C14	0.8527 (3)	0.2655 (6)	0.4541 (3)	0.0348 (9)
F14	0.96520 (18)	0.2329 (3)	0.47752 (18)	0.0449 (7)
C15	0.7783 (3)	0.0905 (6)	0.4631 (3)	0.0342 (9)
C16	0.6638 (3)	0.1251 (6)	0.4384 (3)	0.0338 (9)
H3	0.2873	0.8345	0.3135	0.040*
H5	0.0247	0.4319	0.2777	0.044*
H6	0.1398	0.1303	0.3149	0.043*
H17	0.4560	0.2268	0.3762	0.037*
H12	0.6780	0.6532	0.3767	0.039*
H13	0.8707	0.5927	0.4158	0.041*
H15	0.8044	−0.0516	0.4858	0.041*
H16	0.6112	0.0048	0.4435	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0302 (18)	0.0240 (17)	0.0415 (19)	−0.0009 (13)	−0.0056 (14)	−0.0009 (14)
C2	0.030 (2)	0.028 (2)	0.032 (2)	0.0012 (16)	−0.0029 (16)	0.0000 (16)
C3	0.036 (2)	0.026 (2)	0.037 (2)	−0.0013 (16)	−0.0019 (18)	0.0013 (16)
N4	0.037 (2)	0.0278 (17)	0.043 (2)	−0.0006 (14)	−0.0049 (15)	0.0018 (15)
C5	0.031 (2)	0.034 (2)	0.044 (2)	0.0007 (17)	−0.0048 (17)	−0.0025 (18)
C6	0.033 (2)	0.025 (2)	0.049 (3)	−0.0009 (17)	−0.0033 (18)	0.0015 (18)
C7	0.037 (2)	0.023 (2)	0.034 (2)	−0.0002 (16)	−0.0007 (17)	−0.0022 (16)
O7	0.0354 (16)	0.0243 (14)	0.0562 (18)	−0.0021 (12)	−0.0055 (13)	0.0023 (12)
N17	0.0272 (17)	0.0242 (15)	0.0411 (18)	−0.0025 (13)	−0.0064 (13)	−0.0034 (13)
C11	0.030 (2)	0.0223 (18)	0.033 (2)	0.0020 (15)	−0.0034 (16)	−0.0029 (16)
C12	0.027 (2)	0.0251 (19)	0.046 (2)	−0.0024 (16)	−0.0017 (17)	−0.0011 (17)
C13	0.035 (2)	0.0209 (19)	0.047 (2)	−0.0010 (16)	0.0009 (17)	−0.0018 (17)
C14	0.026 (2)	0.032 (2)	0.046 (2)	0.0013 (17)	−0.0073 (17)	−0.0053 (18)
F14	0.0294 (13)	0.0337 (12)	0.0713 (17)	0.0024 (10)	−0.0065 (11)	0.0012 (11)
C15	0.033 (2)	0.0246 (19)	0.045 (2)	0.0035 (16)	−0.0066 (17)	0.0005 (18)
C16	0.036 (2)	0.0226 (19)	0.043 (2)	−0.0022 (17)	−0.0025 (17)	−0.0032 (17)

Geometric parameters (Å, º)

N1—C2	1.335 (4)	N17—H17	0.9861
N1—C6	1.339 (4)	C11—C12	1.393 (5)
C2—C3	1.387 (5)	C11—C16	1.401 (5)
C2—C7	1.508 (5)	C12—C13	1.382 (5)
C3—N4	1.336 (5)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.382 (5)
N4—C5	1.339 (5)	C13—H13	0.95
C5—C6	1.383 (5)	C14—F14	1.362 (4)
C5—H5	0.95	C14—C15	1.368 (5)
C6—H6	0.95	C15—C16	1.391 (5)
C7—O7	1.234 (4)	C15—H15	0.95
C7—N17	1.353 (5)	C16—H16	0.95
N17—C11	1.406 (4)
C2—N1—C6	115.2 (3)	C11—N17—H17	123.0
N1—C2—C3	122.4 (3)	C12—C11—C16	118.9 (3)
N1—C2—C7	118.3 (3)	C12—C11—N17	123.7 (3)
C3—C2—C7	119.2 (3)	C16—C11—N17	117.4 (3)
N4—C3—C2	122.3 (3)	C13—C12—C11	120.2 (3)
N4—C3—H3	118.9	C13—C12—H12	119.9
C2—C3—H3	118.9	C11—C12—H12	119.9
C3—N4—C5	115.4 (3)	C14—C13—C12	119.4 (3)
N4—C5—C6	122.2 (4)	C14—C13—H13	120.3
N4—C5—H5	118.9	C12—C13—H13	120.3
C6—C5—H5	118.9	F14—C14—C15	119.0 (3)
N1—C6—C5	122.5 (3)	F14—C14—C13	119.0 (3)
N1—C6—H6	118.7	C15—C14—C13	122.0 (3)
C5—C6—H6	118.7	C14—C15—C16	118.6 (3)
O7—C7—N17	125.4 (3)	C14—C15—H15	120.7
O7—C7—C2	120.2 (3)	C16—C15—H15	120.7
N17—C7—C2	114.4 (3)	C15—C16—C11	120.8 (3)
C7—N17—C11	128.1 (3)	C15—C16—H16	119.6
C7—N17—H17	108.8	C11—C16—H16	119.6
C6—N1—C2—C3	−0.1 (5)	C2—C7—N17—C11	179.4 (3)
C6—N1—C2—C7	−179.9 (3)	C7—N17—C11—C12	−7.9 (6)
N1—C2—C3—N4	−0.2 (6)	C7—N17—C11—C16	173.0 (3)
C7—C2—C3—N4	179.6 (3)	C16—C11—C12—C13	0.4 (5)
C2—C3—N4—C5	0.3 (5)	N17—C11—C12—C13	−178.8 (3)
C3—N4—C5—C6	−0.1 (6)	C11—C12—C13—C14	−0.7 (6)
C2—N1—C6—C5	0.3 (5)	C12—C13—C14—F14	−179.7 (3)
N4—C5—C6—N1	−0.2 (6)	C12—C13—C14—C15	0.4 (6)
N1—C2—C7—O7	179.5 (3)	F14—C14—C15—C16	−179.5 (3)
C3—C2—C7—O7	−0.3 (5)	C13—C14—C15—C16	0.3 (6)
N1—C2—C7—N17	−2.2 (5)	C14—C15—C16—C11	−0.7 (5)
C3—C2—C7—N17	178.0 (3)	C12—C11—C16—C15	0.4 (5)
O7—C7—N17—C11	−2.3 (6)	N17—C11—C16—C15	179.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.99	2.11	2.700 (4)	117
C16—H16···O7^i	0.95	2.43	3.271 (4)	147

Symmetry code: (i) x, y−1, z.

(Xb) N-(4-fluorophenyl)pyrazinecarboxamide, Pc polymorph

Crystal data

C11H8FN3O	F(000) = 896
Mr = 217.20	Dx = 1.533 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4277 reflections
a = 5.9666 (3) Å	θ = 3.4–27.5°
b = 24.2205 (15) Å	µ = 0.12 mm^−1
c = 13.0262 (7) Å	T = 120 K
β = 91.720 (3)°	Lath, colourless
V = 1881.62 (18) Å^3	0.18 × 0.11 × 0.05 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	4277 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ϕ & ω scans	h = −7→7
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −31→31
Tmin = 0.966, Tmax = 0.994	l = −16→16
16896 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 0.8298P] where P = (Fo^2 + 2Fc^2)/3
4277 reflections	(Δ/σ)max < 0.001
577 parameters	Δρmax = 0.24 e Å^−3
2 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.3515 (5)	0.07590 (13)	0.1753 (2)	0.0231 (7)
C12	0.1414 (6)	0.09398 (16)	0.1882 (3)	0.0176 (8)
C13	−0.0403 (7)	0.05824 (16)	0.1897 (3)	0.0221 (8)
N14	−0.0184 (6)	0.00369 (14)	0.1775 (3)	0.0248 (8)
C15	0.1907 (7)	−0.01413 (16)	0.1643 (3)	0.0250 (9)
C16	0.3731 (7)	0.02158 (16)	0.1636 (3)	0.0251 (9)
C17	0.1042 (6)	0.15475 (17)	0.2035 (3)	0.0196 (8)
O17	−0.0873 (4)	0.17274 (12)	0.2150 (2)	0.0250 (6)
N117	0.2914 (5)	0.18555 (13)	0.2010 (2)	0.0190 (7)
C111	0.3124 (6)	0.24344 (16)	0.2137 (3)	0.0192 (8)
C112	0.1402 (7)	0.27688 (17)	0.2483 (3)	0.0235 (9)
C113	0.1737 (7)	0.33316 (16)	0.2596 (3)	0.0225 (9)
C114	0.3791 (7)	0.35494 (16)	0.2366 (3)	0.0227 (9)
F14	0.4134 (4)	0.41070 (9)	0.24718 (19)	0.0315 (6)
C115	0.5530 (6)	0.32297 (17)	0.2037 (3)	0.0223 (9)
C116	0.5189 (6)	0.26675 (16)	0.1920 (3)	0.0205 (8)
N21	0.3936 (5)	0.37864 (13)	0.4920 (2)	0.0199 (7)
C22	0.6030 (7)	0.36050 (16)	0.4853 (3)	0.0183 (8)
C23	0.7856 (7)	0.39534 (16)	0.4870 (3)	0.0214 (8)
N24	0.7650 (5)	0.45039 (13)	0.4967 (3)	0.0220 (7)
C25	0.5539 (7)	0.46873 (17)	0.5036 (3)	0.0246 (9)
C26	0.3722 (7)	0.43333 (17)	0.5015 (3)	0.0244 (9)
C27	0.6422 (6)	0.29927 (15)	0.4737 (3)	0.0189 (8)
O27	0.8347 (5)	0.28133 (11)	0.4678 (2)	0.0271 (7)
N217	0.4545 (5)	0.26840 (13)	0.4713 (2)	0.0199 (7)
C211	0.4347 (6)	0.21056 (15)	0.4587 (3)	0.0182 (8)
C212	0.6088 (6)	0.17798 (16)	0.4249 (3)	0.0201 (8)
C213	0.5766 (6)	0.12160 (16)	0.4132 (3)	0.0213 (8)
C214	0.3739 (6)	0.09897 (15)	0.4350 (3)	0.0204 (9)
F24	0.3435 (4)	0.04361 (9)	0.42357 (18)	0.0301 (6)
C215	0.1962 (6)	0.13036 (17)	0.4682 (3)	0.0234 (9)
C216	0.2289 (6)	0.18641 (16)	0.4805 (3)	0.0200 (8)
N31	0.8610 (6)	0.21272 (13)	0.7068 (2)	0.0210 (7)
C32	0.6520 (7)	0.23102 (17)	0.7179 (3)	0.0182 (8)
C33	0.4687 (6)	0.19582 (16)	0.7176 (3)	0.0217 (9)
N34	0.4899 (6)	0.14094 (14)	0.7064 (3)	0.0232 (8)
C35	0.7000 (7)	0.12284 (17)	0.6947 (3)	0.0226 (9)
C36	0.8828 (7)	0.15823 (16)	0.6954 (3)	0.0214 (8)
C37	0.6149 (6)	0.29188 (17)	0.7302 (3)	0.0202 (8)
O37	0.4236 (4)	0.31069 (11)	0.7362 (2)	0.0273 (6)
N317	0.8056 (5)	0.32238 (13)	0.7331 (2)	0.0211 (7)
C311	0.8282 (7)	0.38047 (16)	0.7413 (3)	0.0211 (9)
C312	0.6505 (6)	0.41461 (16)	0.7691 (3)	0.0205 (8)
C313	0.6831 (6)	0.47105 (16)	0.7752 (3)	0.0225 (9)
C314	0.8899 (7)	0.49237 (15)	0.7526 (3)	0.0227 (9)
F34	0.9194 (4)	0.54847 (9)	0.7564 (2)	0.0341 (6)
C315	1.0677 (6)	0.46003 (17)	0.7257 (3)	0.0232 (9)
C316	1.0335 (7)	0.40310 (16)	0.7196 (3)	0.0230 (9)
N41	0.9132 (5)	0.33130 (14)	0.9916 (2)	0.0209 (7)
C42	1.1217 (6)	0.31359 (16)	0.9762 (3)	0.0185 (8)
C43	1.3028 (7)	0.34930 (16)	0.9735 (3)	0.0219 (9)
N44	1.2801 (6)	0.40379 (14)	0.9867 (3)	0.0245 (8)
C45	1.0719 (7)	0.42164 (17)	1.0019 (3)	0.0238 (9)
C46	0.8907 (6)	0.38583 (16)	1.0052 (3)	0.0229 (9)
C47	1.1603 (7)	0.25279 (16)	0.9618 (3)	0.0195 (8)
O47	1.3490 (4)	0.23480 (11)	0.9495 (2)	0.0251 (6)
N417	0.9707 (5)	0.22207 (13)	0.9639 (3)	0.0210 (7)
C411	0.9485 (6)	0.16455 (15)	0.9530 (3)	0.0181 (8)
C412	1.1228 (6)	0.13037 (16)	0.9208 (3)	0.0215 (8)
C413	1.0851 (6)	0.07398 (17)	0.9098 (3)	0.0224 (9)
C414	0.8782 (7)	0.05219 (16)	0.9296 (3)	0.0230 (9)
F44	0.8449 (4)	−0.00270 (9)	0.9197 (2)	0.0322 (6)
C415	0.7061 (6)	0.08510 (17)	0.9612 (3)	0.0240 (9)
C416	0.7387 (6)	0.14112 (16)	0.9731 (3)	0.0215 (9)
H13	−0.1854	0.0731	0.1998	0.027*
H15	0.2156	−0.0525	0.1550	0.030*
H16	0.5184	0.0067	0.1544	0.030*
H117	0.4173	0.1672	0.1942	0.023*
H112	−0.0003	0.2611	0.2641	0.028*
H113	0.0571	0.3563	0.2829	0.027*
H115	0.6938	0.3391	0.1892	0.027*
H116	0.6370	0.2440	0.1691	0.025*
H23	0.9311	0.3799	0.4812	0.026*
H25	0.5285	0.5073	0.5101	0.030*
H26	0.2262	0.4485	0.5071	0.029*
H217	0.3331	0.2884	0.4793	0.024*
H212	0.7491	0.1942	0.4098	0.024*
H213	0.6947	0.0989	0.3902	0.026*
H215	0.0560	0.1138	0.4821	0.028*
H216	0.1103	0.2088	0.5041	0.024*
H33	0.3234	0.2110	0.7256	0.026*
H35	0.7245	0.0844	0.6855	0.027*
H36	1.0283	0.1432	0.6876	0.026*
H317	0.9313	0.3047	0.7216	0.025*
H312	0.5087	0.3991	0.7837	0.025*
H313	0.5648	0.4947	0.7947	0.027*
H315	1.2092	0.4759	0.7117	0.028*
H316	1.1529	0.3797	0.7004	0.028*
H43	1.4476	0.3347	0.9620	0.026*
H45	1.0471	0.4601	1.0107	0.029*
H46	0.7462	0.4004	1.0176	0.027*
H417	0.8539	0.2424	0.9789	0.025*
H412	1.2653	0.1456	0.9067	0.026*
H413	1.2026	0.0505	0.8886	0.027*
H415	0.5644	0.0693	0.9749	0.029*
H416	0.6195	0.1639	0.9948	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0263 (18)	0.0146 (17)	0.0282 (18)	0.0000 (14)	0.0011 (14)	−0.0034 (14)
C12	0.0170 (19)	0.019 (2)	0.0169 (18)	0.0004 (15)	−0.0019 (15)	0.0019 (15)
C13	0.022 (2)	0.020 (2)	0.025 (2)	0.0010 (17)	0.0035 (15)	−0.0038 (16)
N14	0.0234 (18)	0.0202 (18)	0.0309 (19)	0.0003 (14)	0.0013 (14)	−0.0003 (14)
C15	0.031 (2)	0.014 (2)	0.030 (2)	0.0026 (17)	0.0034 (17)	−0.0002 (16)
C16	0.021 (2)	0.021 (2)	0.034 (2)	0.0018 (17)	0.0047 (16)	−0.0029 (17)
C17	0.019 (2)	0.020 (2)	0.0205 (19)	−0.0002 (16)	−0.0021 (15)	−0.0005 (15)
O17	0.0186 (15)	0.0218 (15)	0.0347 (17)	−0.0008 (12)	0.0029 (12)	−0.0019 (12)
N117	0.0196 (17)	0.0139 (16)	0.0236 (17)	0.0022 (13)	0.0032 (13)	−0.0020 (13)
C111	0.021 (2)	0.018 (2)	0.0185 (19)	0.0014 (16)	0.0002 (16)	−0.0014 (15)
C112	0.018 (2)	0.024 (2)	0.029 (2)	0.0005 (17)	−0.0002 (16)	−0.0018 (17)
C113	0.023 (2)	0.015 (2)	0.030 (2)	0.0012 (17)	−0.0003 (17)	−0.0015 (16)
C114	0.028 (2)	0.0128 (19)	0.027 (2)	−0.0035 (17)	−0.0029 (18)	0.0003 (16)
F14	0.0306 (13)	0.0155 (12)	0.0482 (15)	−0.0028 (10)	−0.0017 (11)	−0.0043 (11)
C115	0.017 (2)	0.021 (2)	0.029 (2)	−0.0050 (16)	0.0008 (16)	0.0056 (17)
C116	0.021 (2)	0.020 (2)	0.021 (2)	0.0005 (16)	−0.0007 (15)	−0.0022 (15)
N21	0.0178 (17)	0.0165 (17)	0.0255 (17)	0.0013 (14)	0.0040 (13)	−0.0009 (13)
C22	0.022 (2)	0.020 (2)	0.0130 (17)	0.0004 (16)	0.0008 (14)	0.0015 (15)
C23	0.022 (2)	0.019 (2)	0.023 (2)	−0.0021 (16)	0.0005 (16)	0.0020 (16)
N24	0.0216 (17)	0.0179 (17)	0.0267 (18)	−0.0046 (14)	0.0020 (13)	−0.0015 (13)
C25	0.025 (2)	0.019 (2)	0.030 (2)	0.0002 (17)	−0.0010 (17)	0.0006 (17)
C26	0.024 (2)	0.020 (2)	0.030 (2)	0.0034 (17)	0.0037 (16)	−0.0029 (16)
C27	0.021 (2)	0.020 (2)	0.0162 (18)	0.0016 (16)	0.0009 (15)	0.0000 (16)
O27	0.0203 (15)	0.0207 (15)	0.0402 (17)	0.0038 (12)	0.0016 (12)	−0.0027 (13)
N217	0.0175 (16)	0.0181 (18)	0.0240 (17)	0.0015 (13)	0.0018 (13)	−0.0012 (13)
C211	0.020 (2)	0.015 (2)	0.0190 (19)	0.0001 (16)	−0.0011 (15)	0.0011 (15)
C212	0.016 (2)	0.019 (2)	0.026 (2)	−0.0028 (16)	0.0044 (15)	0.0004 (16)
C213	0.022 (2)	0.0169 (19)	0.025 (2)	0.0041 (16)	0.0011 (16)	−0.0034 (16)
C214	0.022 (2)	0.0144 (19)	0.025 (2)	−0.0018 (16)	−0.0036 (16)	0.0003 (15)
F24	0.0306 (14)	0.0152 (12)	0.0443 (15)	−0.0045 (10)	0.0018 (11)	−0.0016 (11)
C215	0.021 (2)	0.025 (2)	0.024 (2)	−0.0018 (17)	0.0010 (16)	0.0012 (16)
C216	0.017 (2)	0.022 (2)	0.021 (2)	0.0017 (16)	−0.0003 (15)	0.0015 (15)
N31	0.0250 (18)	0.0156 (17)	0.0227 (17)	0.0007 (15)	0.0036 (13)	−0.0005 (14)
C32	0.021 (2)	0.017 (2)	0.0163 (18)	0.0049 (16)	−0.0010 (15)	0.0016 (14)
C33	0.0164 (19)	0.024 (2)	0.025 (2)	0.0033 (16)	0.0040 (16)	0.0011 (16)
N34	0.0239 (18)	0.0206 (19)	0.0251 (18)	−0.0021 (15)	−0.0007 (14)	0.0020 (14)
C35	0.028 (2)	0.016 (2)	0.025 (2)	0.0027 (17)	0.0022 (17)	−0.0016 (16)
C36	0.023 (2)	0.021 (2)	0.0201 (19)	0.0052 (16)	0.0002 (15)	−0.0004 (15)
C37	0.023 (2)	0.020 (2)	0.0172 (19)	0.0020 (16)	−0.0029 (15)	0.0014 (15)
O37	0.0207 (15)	0.0182 (14)	0.0432 (17)	0.0016 (12)	0.0029 (12)	0.0000 (12)
N317	0.0214 (18)	0.0164 (17)	0.0257 (18)	0.0012 (14)	0.0016 (14)	−0.0016 (14)
C311	0.024 (2)	0.016 (2)	0.023 (2)	−0.0013 (16)	−0.0020 (15)	−0.0002 (16)
C312	0.0180 (19)	0.022 (2)	0.0213 (19)	0.0042 (16)	0.0013 (15)	−0.0002 (15)
C313	0.020 (2)	0.020 (2)	0.028 (2)	0.0016 (16)	0.0002 (16)	0.0002 (16)
C314	0.025 (2)	0.0128 (19)	0.030 (2)	−0.0022 (17)	0.0006 (17)	−0.0008 (16)
F34	0.0312 (14)	0.0173 (12)	0.0539 (16)	−0.0039 (11)	0.0021 (12)	−0.0038 (12)
C315	0.015 (2)	0.023 (2)	0.031 (2)	−0.0032 (16)	−0.0005 (16)	0.0007 (17)
C316	0.022 (2)	0.019 (2)	0.029 (2)	0.0054 (16)	0.0025 (17)	−0.0017 (16)
N41	0.0205 (17)	0.0172 (17)	0.0249 (17)	−0.0011 (14)	0.0000 (14)	0.0011 (13)
C42	0.021 (2)	0.018 (2)	0.0160 (19)	0.0000 (16)	−0.0029 (15)	0.0005 (15)
C43	0.024 (2)	0.020 (2)	0.022 (2)	0.0008 (17)	0.0019 (16)	−0.0001 (16)
N44	0.0268 (19)	0.0186 (18)	0.0280 (19)	−0.0014 (15)	0.0018 (14)	−0.0009 (14)
C45	0.029 (2)	0.015 (2)	0.028 (2)	0.0005 (17)	0.0005 (17)	0.0010 (16)
C46	0.020 (2)	0.021 (2)	0.028 (2)	−0.0006 (16)	0.0041 (16)	−0.0007 (16)
C47	0.021 (2)	0.019 (2)	0.0182 (18)	0.0009 (17)	0.0005 (15)	0.0008 (15)
O47	0.0193 (14)	0.0211 (14)	0.0351 (16)	0.0018 (12)	0.0020 (12)	−0.0023 (12)
N417	0.0190 (17)	0.0180 (18)	0.0262 (17)	0.0035 (14)	0.0029 (13)	−0.0023 (14)
C411	0.021 (2)	0.0146 (19)	0.0189 (18)	0.0014 (16)	−0.0017 (15)	0.0014 (14)
C412	0.0194 (19)	0.018 (2)	0.027 (2)	−0.0045 (16)	−0.0005 (15)	−0.0025 (17)
C413	0.020 (2)	0.021 (2)	0.026 (2)	0.0042 (17)	−0.0017 (16)	−0.0016 (16)
C414	0.028 (2)	0.015 (2)	0.025 (2)	−0.0024 (17)	−0.0012 (17)	0.0002 (16)
F44	0.0320 (14)	0.0132 (11)	0.0513 (16)	−0.0040 (10)	0.0016 (11)	−0.0026 (11)
C415	0.020 (2)	0.022 (2)	0.030 (2)	−0.0020 (16)	−0.0016 (16)	0.0001 (17)
C416	0.021 (2)	0.023 (2)	0.020 (2)	0.0014 (17)	−0.0018 (16)	−0.0018 (16)

Geometric parameters (Å, º)

N11—C16	1.331 (5)	N31—C36	1.335 (5)
N11—C12	1.343 (5)	N31—C32	1.336 (5)
C12—C13	1.388 (5)	C32—C33	1.387 (6)
C12—C17	1.503 (5)	C32—C37	1.500 (5)
C13—N14	1.338 (5)	C33—N34	1.343 (5)
C13—H13	0.95	C33—H33	0.95
N14—C15	1.336 (5)	N34—C35	1.341 (5)
C15—C16	1.390 (6)	C35—C36	1.387 (6)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—O17	1.236 (5)	C37—O37	1.234 (5)
C17—N117	1.344 (5)	C37—N317	1.356 (5)
N117—C111	1.417 (5)	N317—C311	1.417 (5)
N117—H117	0.88	N317—H317	0.88
C111—C116	1.392 (5)	C311—C316	1.379 (6)
C111—C112	1.394 (5)	C311—C312	1.401 (5)
C112—C113	1.385 (6)	C312—C313	1.383 (5)
C112—H112	0.95	C312—H312	0.95
C113—C114	1.375 (5)	C313—C314	1.378 (5)
C113—H113	0.95	C313—H313	0.95
C114—F14	1.372 (4)	C314—F34	1.371 (4)
C114—C115	1.374 (6)	C314—C315	1.372 (6)
C115—C116	1.385 (5)	C315—C316	1.396 (5)
C115—H115	0.95	C315—H315	0.95
C116—H116	0.95	C316—H316	0.95
N21—C22	1.330 (5)	N41—C42	1.336 (5)
N21—C26	1.337 (5)	N41—C46	1.340 (5)
C22—C23	1.378 (5)	C42—C43	1.386 (6)
C22—C27	1.510 (5)	C42—C47	1.503 (5)
C23—N24	1.345 (5)	C43—N44	1.338 (5)
C23—H23	0.95	C43—H43	0.95
N24—C25	1.341 (5)	N44—C45	1.335 (5)
C25—C26	1.382 (6)	C45—C46	1.388 (6)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95
C27—O27	1.232 (5)	C47—O47	1.222 (5)
C27—N217	1.346 (5)	C47—N417	1.355 (5)
N217—C211	1.415 (5)	N417—C411	1.406 (5)
N217—H217	0.88	N417—H417	0.88
C211—C212	1.387 (5)	C411—C412	1.403 (5)
C211—C216	1.397 (5)	C411—C416	1.406 (6)
C212—C213	1.387 (5)	C412—C413	1.391 (6)
C212—H212	0.95	C412—H412	0.95
C213—C214	1.365 (5)	C413—C414	1.374 (6)
C213—H213	0.95	C413—H413	0.95
C214—F24	1.361 (4)	C414—F44	1.350 (4)
C214—C215	1.385 (5)	C414—C415	1.373 (5)
C215—C216	1.380 (5)	C415—C416	1.379 (5)
C215—H215	0.95	C415—H415	0.95
C216—H216	0.95	C416—H416	0.95
C16—N11—C12	115.5 (3)	C36—N31—C32	115.8 (3)
N11—C12—C13	122.1 (4)	N31—C32—C33	122.3 (4)
N11—C12—C17	118.5 (3)	N31—C32—C37	118.6 (4)
C13—C12—C17	119.4 (3)	C33—C32—C37	119.0 (3)
N14—C13—C12	122.3 (4)	N34—C33—C32	122.1 (4)
N14—C13—H13	118.8	N34—C33—H33	118.9
C12—C13—H13	118.8	C32—C33—H33	118.9
C15—N14—C13	115.4 (4)	C35—N34—C33	115.3 (4)
N14—C15—C16	122.3 (4)	N34—C35—C36	122.3 (4)
N14—C15—H15	118.9	N34—C35—H35	118.8
C16—C15—H15	118.9	C36—C35—H35	118.8
N11—C16—C15	122.4 (4)	N31—C36—C35	122.2 (4)
N11—C16—H16	118.8	N31—C36—H36	118.9
C15—C16—H16	118.8	C35—C36—H36	118.9
O17—C17—N117	125.4 (4)	O37—C37—N317	125.0 (4)
O17—C17—C12	120.1 (4)	O37—C37—C32	120.6 (4)
N117—C17—C12	114.5 (3)	N317—C37—C32	114.3 (3)
C17—N117—C111	128.1 (3)	C37—N317—C311	128.4 (3)
C17—N117—H117	115.7	C37—N317—H317	116.7
C111—N117—H117	116.0	C311—N317—H317	114.5
C116—C111—C112	119.7 (4)	C316—C311—C312	120.1 (4)
C116—C111—N117	117.0 (3)	C316—C311—N317	117.5 (4)
C112—C111—N117	123.3 (4)	C312—C311—N317	122.3 (4)
C113—C112—C111	120.1 (4)	C313—C312—C311	119.5 (4)
C113—C112—H112	120.0	C313—C312—H312	120.3
C111—C112—H112	120.0	C311—C312—H312	120.3
C114—C113—C112	118.8 (4)	C314—C313—C312	118.9 (4)
C114—C113—H113	120.6	C314—C313—H313	120.5
C112—C113—H113	120.6	C312—C313—H313	120.5
F14—C114—C115	118.3 (4)	F34—C314—C315	118.4 (4)
F14—C114—C113	119.1 (4)	F34—C314—C313	118.6 (3)
C115—C114—C113	122.6 (4)	C315—C314—C313	123.0 (4)
C114—C115—C116	118.6 (3)	C314—C315—C316	117.7 (4)
C114—C115—H115	120.7	C314—C315—H315	121.1
C116—C115—H115	120.7	C316—C315—H315	121.1
C115—C116—C111	120.3 (4)	C311—C316—C315	120.7 (4)
C115—C116—H116	119.8	C311—C316—H316	119.7
C111—C116—H116	119.8	C315—C316—H316	119.7
C22—N21—C26	115.2 (3)	C42—N41—C46	115.7 (3)
N21—C22—C23	122.7 (4)	N41—C42—C43	122.3 (4)
N21—C22—C27	118.7 (3)	N41—C42—C47	118.7 (3)
C23—C22—C27	118.6 (3)	C43—C42—C47	119.0 (3)
N24—C23—C22	122.3 (4)	N44—C43—C42	122.0 (4)
N24—C23—H23	118.9	N44—C43—H43	119.0
C22—C23—H23	118.9	C42—C43—H43	119.0
C25—N24—C23	115.0 (3)	C45—N44—C43	115.9 (4)
N24—C25—C26	122.1 (4)	N44—C45—C46	122.1 (4)
N24—C25—H25	119.0	N44—C45—H45	118.9
C26—C25—H25	119.0	C46—C45—H45	118.9
N21—C26—C25	122.7 (4)	N41—C46—C45	122.0 (4)
N21—C26—H26	118.7	N41—C46—H46	119.0
C25—C26—H26	118.7	C45—C46—H46	119.0
O27—C27—N217	125.4 (4)	O47—C47—N417	125.4 (4)
O27—C27—C22	120.0 (4)	O47—C47—C42	120.7 (4)
N217—C27—C22	114.6 (3)	N417—C47—C42	113.8 (3)
C27—N217—C211	128.2 (3)	C47—N417—C411	128.2 (4)
C27—N217—H217	112.3	C47—N417—H417	111.4
C211—N217—H217	119.5	C411—N417—H417	120.2
C212—C211—C216	119.9 (3)	C412—C411—C416	119.3 (3)
C212—C211—N217	122.7 (3)	C412—C411—N417	123.1 (4)
C216—C211—N217	117.5 (3)	C416—C411—N417	117.6 (3)
C211—C212—C213	119.5 (4)	C413—C412—C411	119.4 (4)
C211—C212—H212	120.2	C413—C412—H412	120.3
C213—C212—H212	120.2	C411—C412—H412	120.3
C214—C213—C212	119.6 (4)	C414—C413—C412	120.1 (4)
C214—C213—H213	120.2	C414—C413—H413	120.0
C212—C213—H213	120.2	C412—C413—H413	120.0
F24—C214—C213	119.3 (3)	F44—C414—C415	119.4 (4)
F24—C214—C215	118.3 (3)	F44—C414—C413	119.4 (3)
C213—C214—C215	122.4 (4)	C415—C414—C413	121.2 (4)
C216—C215—C214	118.0 (4)	C414—C415—C416	120.1 (4)
C216—C215—H215	121.0	C414—C415—H415	120.0
C214—C215—H215	121.0	C416—C415—H415	120.0
C215—C216—C211	120.7 (4)	C415—C416—C411	120.0 (4)
C215—C216—H216	119.7	C415—C416—H416	120.0
C211—C216—H216	119.7	C411—C416—H416	120.0
C16—N11—C12—C13	0.4 (5)	C36—N31—C32—C33	−0.1 (5)
C16—N11—C12—C17	179.1 (3)	C36—N31—C32—C37	−179.5 (3)
N11—C12—C13—N14	−0.7 (6)	N31—C32—C33—N34	0.2 (6)
C17—C12—C13—N14	−179.4 (4)	C37—C32—C33—N34	179.6 (3)
C12—C13—N14—C15	0.4 (6)	C32—C33—N34—C35	−0.6 (6)
C13—N14—C15—C16	0.2 (6)	C33—N34—C35—C36	0.9 (6)
C12—N11—C16—C15	0.2 (6)	C32—N31—C36—C35	0.3 (6)
N14—C15—C16—N11	−0.5 (6)	N34—C35—C36—N31	−0.8 (6)
N11—C12—C17—O17	179.6 (3)	N31—C32—C37—O37	176.9 (3)
C13—C12—C17—O17	−1.7 (5)	C33—C32—C37—O37	−2.5 (5)
N11—C12—C17—N117	1.0 (5)	N31—C32—C37—N317	−2.8 (5)
C13—C12—C17—N117	179.7 (3)	C33—C32—C37—N317	177.8 (3)
O17—C17—N117—C111	2.0 (6)	O37—C37—N317—C311	−1.4 (6)
C12—C17—N117—C111	−179.4 (3)	C32—C37—N317—C311	178.2 (3)
C17—N117—C111—C116	−170.2 (4)	C37—N317—C311—C316	−165.7 (4)
C17—N117—C111—C112	11.2 (6)	C37—N317—C311—C312	13.7 (6)
C116—C111—C112—C113	0.9 (6)	C316—C311—C312—C313	−0.3 (6)
N117—C111—C112—C113	179.4 (3)	N317—C311—C312—C313	−179.7 (4)
C111—C112—C113—C114	−0.3 (6)	C311—C312—C313—C314	0.6 (6)
C112—C113—C114—F14	179.7 (4)	C312—C313—C314—F34	178.4 (3)
C112—C113—C114—C115	−0.6 (6)	C312—C313—C314—C315	−1.1 (6)
F14—C114—C115—C116	−179.4 (3)	F34—C314—C315—C316	−178.4 (3)
C113—C114—C115—C116	0.9 (6)	C313—C314—C315—C316	1.1 (6)
C114—C115—C116—C111	−0.2 (6)	C312—C311—C316—C315	0.3 (6)
C112—C111—C116—C115	−0.6 (6)	N317—C311—C316—C315	179.8 (4)
N117—C111—C116—C115	−179.3 (3)	C314—C315—C316—C311	−0.7 (6)
C26—N21—C22—C23	−0.5 (5)	C46—N41—C42—C43	−0.6 (5)
C26—N21—C22—C27	−179.6 (3)	C46—N41—C42—C47	179.2 (3)
N21—C22—C23—N24	0.6 (6)	N41—C42—C43—N44	0.3 (6)
C27—C22—C23—N24	179.7 (3)	C47—C42—C43—N44	−179.4 (4)
C22—C23—N24—C25	−0.5 (5)	C42—C43—N44—C45	−0.5 (6)
C23—N24—C25—C26	0.4 (6)	C43—N44—C45—C46	0.9 (6)
C22—N21—C26—C25	0.4 (6)	C42—N41—C46—C45	1.0 (5)
N24—C25—C26—N21	−0.4 (6)	N44—C45—C46—N41	−1.2 (6)
N21—C22—C27—O27	−179.6 (4)	N41—C42—C47—O47	−178.6 (3)
C23—C22—C27—O27	1.3 (5)	C43—C42—C47—O47	1.1 (5)
N21—C22—C27—N217	0.0 (5)	N41—C42—C47—N417	1.5 (5)
C23—C22—C27—N217	−179.2 (3)	C43—C42—C47—N417	−178.8 (3)
O27—C27—N217—C211	−2.2 (6)	O47—C47—N417—C411	0.2 (7)
C22—C27—N217—C211	178.2 (3)	C42—C47—N417—C411	−179.9 (4)
C27—N217—C211—C212	−14.1 (6)	C47—N417—C411—C412	−10.9 (6)
C27—N217—C211—C216	166.7 (4)	C47—N417—C411—C416	170.7 (4)
C216—C211—C212—C213	−0.1 (6)	C416—C411—C412—C413	−0.3 (6)
N217—C211—C212—C213	−179.3 (3)	N417—C411—C412—C413	−178.6 (4)
C211—C212—C213—C214	0.1 (6)	C411—C412—C413—C414	0.5 (6)
C212—C213—C214—F24	−179.9 (3)	C412—C413—C414—F44	−179.2 (3)
C212—C213—C214—C215	0.4 (6)	C412—C413—C414—C415	−0.6 (6)
F24—C214—C215—C216	179.4 (3)	F44—C414—C415—C416	179.0 (3)
C213—C214—C215—C216	−0.8 (6)	C413—C414—C415—C416	0.4 (6)
C214—C215—C216—C211	0.8 (6)	C414—C415—C416—C411	−0.1 (6)
C212—C211—C216—C215	−0.4 (6)	C412—C411—C416—C415	0.1 (6)
N217—C211—C216—C215	178.9 (3)	N417—C411—C416—C415	178.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N117—H117···N11	0.88	2.26	2.702 (4)	111
N217—H217···N21	0.88	2.22	2.709 (4)	115
N317—H317···N31	0.88	2.27	2.700 (4)	110
N417—H417···N41	0.88	2.19	2.693 (5)	116
C116—H116···O17^i	0.95	2.45	3.279 (5)	146
C216—H216···O27^ii	0.95	2.44	3.290 (5)	148
C316—H316···O37^i	0.95	2.36	3.232 (5)	152
C416—H416···O47^ii	0.95	2.42	3.257 (5)	147

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

(XII) N-(3-chlorophenyl)pyrazinecarboxamide

Crystal data

C11H8ClN3O	F(000) = 960
Mr = 233.65	Dx = 1.532 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4631 reflections
a = 9.9121 (3) Å	θ = 3.0–28.5°
b = 10.9457 (3) Å	µ = 0.36 mm^−1
c = 18.6827 (4) Å	T = 120 K
β = 92.026 (2)°	Block, colourless
V = 2025.71 (9) Å^3	0.56 × 0.38 × 0.14 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	4631 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 9.091 pixels mm^-1	θmax = 28.5°, θmin = 3.0°
ϕ & ω scans	h = −12→12
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→14
Tmin = 0.826, Tmax = 0.952	l = −24→24
24690 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.3443P] where P = (Fo^2 + 2Fc^2)/3
4631 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.68520 (14)	0.03418 (12)	0.44994 (7)	0.0214 (3)
C12	0.60813 (16)	0.13419 (15)	0.44557 (8)	0.0168 (3)
C13	0.63979 (17)	0.24180 (15)	0.47961 (8)	0.0202 (4)
N14	0.75021 (14)	0.25353 (13)	0.51821 (7)	0.0226 (3)
C15	0.82725 (17)	0.15421 (15)	0.52195 (9)	0.0219 (4)
C16	0.79528 (17)	0.04560 (16)	0.48870 (9)	0.0234 (4)
C17	0.48353 (17)	0.12885 (15)	0.40215 (8)	0.0186 (4)
O17	0.41490 (12)	0.22066 (10)	0.39422 (6)	0.0264 (3)
N117	0.45644 (13)	0.01748 (12)	0.37446 (7)	0.0184 (3)
C111	0.34421 (16)	−0.01228 (14)	0.33304 (8)	0.0171 (3)
C112	0.22190 (16)	0.04940 (15)	0.34182 (8)	0.0187 (4)
C113	0.11576 (16)	0.01290 (15)	0.30065 (8)	0.0201 (4)
Cl11	−0.03790 (4)	0.08933 (4)	0.31289 (2)	0.03134 (13)
C114	0.12680 (17)	−0.08113 (15)	0.25119 (8)	0.0219 (4)
C115	0.24900 (18)	−0.14168 (15)	0.24370 (9)	0.0222 (4)
C116	0.35748 (17)	−0.10832 (15)	0.28444 (8)	0.0189 (4)
N21	0.64872 (13)	0.53564 (12)	0.45662 (7)	0.0187 (3)
C22	0.71960 (16)	0.63832 (15)	0.46389 (8)	0.0176 (3)
C23	0.69223 (17)	0.74304 (15)	0.42529 (9)	0.0228 (4)
N24	0.59012 (14)	0.74892 (13)	0.38048 (7)	0.0246 (3)
C25	0.51974 (17)	0.64604 (16)	0.37338 (8)	0.0221 (4)
C26	0.54907 (16)	0.53989 (15)	0.41006 (8)	0.0202 (4)
C27	0.83076 (16)	0.64210 (15)	0.51698 (8)	0.0181 (4)
O27	0.89224 (11)	0.73743 (10)	0.52635 (6)	0.0245 (3)
N217	0.85269 (13)	0.53503 (12)	0.55113 (7)	0.0191 (3)
C211	0.94885 (16)	0.51168 (15)	0.60367 (8)	0.0174 (3)
C212	1.04908 (16)	0.59501 (15)	0.62050 (8)	0.0175 (3)
C213	1.13894 (16)	0.56285 (15)	0.67256 (8)	0.0193 (4)
Cl21	1.26248 (4)	0.66851 (4)	0.69513 (2)	0.02533 (12)
C214	1.13449 (17)	0.45166 (16)	0.70729 (9)	0.0228 (4)
C215	1.03399 (18)	0.37054 (17)	0.68973 (9)	0.0263 (4)
C216	0.94081 (17)	0.39971 (15)	0.63882 (9)	0.0223 (4)
H13	0.5796	0.3091	0.4748	0.024*
H15	0.9097	0.1586	0.5494	0.026*
H16	0.8548	−0.0221	0.4942	0.028*
H117	0.5171	−0.0392	0.3792	0.022*
H112	0.2145	0.1141	0.3754	0.022*
H114	0.0503	−0.1043	0.2223	0.026*
H115	0.2558	−0.2062	0.2100	0.027*
H116	0.4414	−0.1492	0.2803	0.023*
H23	0.7494	0.8122	0.4317	0.027*
H25	0.4440	0.6458	0.3408	0.027*
H26	0.4957	0.4691	0.4011	0.024*
H217	0.8030	0.4723	0.5389	0.023*
H212	1.0544	0.6713	0.5965	0.021*
H214	1.2010	0.4317	0.7432	0.027*
H215	1.0301	0.2939	0.7135	0.032*
H216	0.8697	0.3444	0.6268	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0207 (8)	0.0198 (8)	0.0231 (7)	0.0008 (6)	−0.0064 (6)	−0.0018 (6)
C12	0.0167 (8)	0.0182 (8)	0.0151 (7)	−0.0008 (7)	−0.0031 (6)	0.0023 (7)
C13	0.0207 (9)	0.0175 (9)	0.0221 (8)	−0.0009 (7)	−0.0062 (7)	0.0006 (7)
N14	0.0226 (8)	0.0200 (8)	0.0246 (7)	−0.0032 (6)	−0.0082 (6)	−0.0005 (6)
C15	0.0186 (9)	0.0247 (10)	0.0221 (8)	−0.0026 (7)	−0.0054 (7)	0.0006 (7)
C16	0.0198 (9)	0.0235 (9)	0.0265 (9)	0.0041 (7)	−0.0063 (7)	−0.0008 (7)
C17	0.0199 (9)	0.0168 (8)	0.0187 (8)	−0.0014 (7)	−0.0042 (7)	0.0017 (7)
O17	0.0256 (7)	0.0172 (6)	0.0352 (7)	0.0028 (5)	−0.0143 (5)	−0.0006 (5)
N117	0.0177 (7)	0.0167 (7)	0.0202 (7)	0.0023 (6)	−0.0081 (6)	−0.0017 (6)
C111	0.0183 (8)	0.0164 (8)	0.0161 (8)	−0.0030 (7)	−0.0059 (6)	0.0039 (6)
C112	0.0212 (9)	0.0173 (9)	0.0172 (8)	−0.0015 (7)	−0.0045 (7)	−0.0002 (7)
C113	0.0174 (9)	0.0218 (9)	0.0209 (8)	0.0000 (7)	−0.0037 (7)	0.0039 (7)
Cl11	0.0190 (2)	0.0396 (3)	0.0347 (3)	0.0059 (2)	−0.00885 (18)	−0.0073 (2)
C114	0.0223 (9)	0.0204 (9)	0.0221 (8)	−0.0043 (7)	−0.0097 (7)	0.0023 (7)
C115	0.0291 (10)	0.0160 (9)	0.0208 (8)	−0.0030 (7)	−0.0069 (7)	−0.0010 (7)
C116	0.0203 (9)	0.0172 (9)	0.0188 (8)	0.0002 (7)	−0.0039 (7)	0.0030 (7)
N21	0.0181 (7)	0.0193 (7)	0.0182 (7)	0.0011 (6)	−0.0049 (6)	−0.0016 (6)
C22	0.0171 (8)	0.0170 (8)	0.0184 (8)	0.0009 (7)	−0.0038 (6)	−0.0034 (7)
C23	0.0219 (9)	0.0178 (9)	0.0280 (9)	0.0000 (7)	−0.0086 (7)	−0.0019 (7)
N24	0.0247 (8)	0.0212 (8)	0.0273 (8)	0.0017 (6)	−0.0095 (6)	0.0013 (6)
C25	0.0212 (9)	0.0253 (10)	0.0193 (8)	0.0030 (7)	−0.0077 (7)	−0.0028 (7)
C26	0.0191 (9)	0.0207 (9)	0.0204 (8)	−0.0015 (7)	−0.0048 (7)	−0.0030 (7)
C27	0.0163 (8)	0.0186 (9)	0.0193 (8)	0.0019 (7)	−0.0028 (7)	−0.0034 (7)
O27	0.0235 (6)	0.0188 (6)	0.0303 (6)	−0.0019 (5)	−0.0122 (5)	−0.0002 (5)
N217	0.0186 (7)	0.0166 (7)	0.0213 (7)	−0.0021 (6)	−0.0091 (6)	−0.0006 (6)
C211	0.0165 (8)	0.0192 (9)	0.0160 (7)	0.0025 (7)	−0.0045 (6)	−0.0028 (7)
C212	0.0179 (8)	0.0176 (9)	0.0170 (8)	0.0021 (7)	−0.0022 (6)	−0.0007 (7)
C213	0.0157 (8)	0.0212 (9)	0.0205 (8)	−0.0002 (7)	−0.0039 (6)	−0.0051 (7)
Cl21	0.0191 (2)	0.0253 (2)	0.0309 (2)	−0.00261 (17)	−0.01019 (17)	−0.00261 (18)
C214	0.0208 (9)	0.0261 (10)	0.0210 (8)	0.0025 (7)	−0.0077 (7)	−0.0001 (7)
C215	0.0290 (10)	0.0224 (9)	0.0267 (9)	0.0006 (8)	−0.0092 (8)	0.0029 (8)
C216	0.0235 (9)	0.0186 (9)	0.0240 (8)	−0.0025 (7)	−0.0085 (7)	−0.0023 (7)

Geometric parameters (Å, º)

N11—C16	1.294 (2)	N21—C26	1.2937 (19)
N11—C12	1.336 (2)	N21—C22	1.330 (2)
C12—C13	1.370 (2)	C22—C23	1.376 (2)
C12—C17	1.455 (2)	C22—C27	1.457 (2)
C13—N14	1.2957 (19)	C23—N24	1.2920 (19)
C13—H13	0.95	C23—H23	0.95
N14—C15	1.329 (2)	N24—C25	1.329 (2)
C15—C16	1.373 (2)	C25—C26	1.375 (2)
C15—H15	0.95	C25—H25	0.95
C16—H16	0.95	C26—H26	0.95
C17—O17	1.2197 (19)	C27—O27	1.2179 (19)
C17—N117	1.348 (2)	C27—N217	1.348 (2)
N117—C111	1.3717 (19)	N217—C211	1.3679 (19)
N117—H117	0.8661	N217—H217	0.8703
C111—C116	1.398 (2)	C211—C212	1.377 (2)
C111—C112	1.402 (2)	C211—C216	1.394 (2)
C112—C113	1.342 (2)	C212—C213	1.342 (2)
C112—H112	0.95	C212—H212	0.95
C113—C114	1.390 (2)	C213—C214	1.381 (2)
C113—Cl11	1.7597 (17)	C213—Cl21	1.7257 (16)
C114—C115	1.392 (2)	C214—C215	1.366 (2)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.346 (2)	C215—C216	1.341 (2)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
C16—N11—C12	115.09 (14)	C26—N21—C22	115.24 (14)
N11—C12—C13	123.73 (14)	N21—C22—C23	123.83 (14)
N11—C12—C17	118.27 (14)	N21—C22—C27	118.54 (14)
C13—C12—C17	118.01 (15)	C23—C22—C27	117.62 (15)
N14—C13—C12	121.25 (16)	N24—C23—C22	121.10 (16)
N14—C13—H13	119.4	N24—C23—H23	119.5
C12—C13—H13	119.4	C22—C23—H23	119.5
C13—N14—C15	114.88 (14)	C23—N24—C25	114.76 (14)
N14—C15—C16	124.15 (15)	N24—C25—C26	124.43 (15)
N14—C15—H15	117.9	N24—C25—H25	117.8
C16—C15—H15	117.9	C26—C25—H25	117.8
N11—C16—C15	120.88 (16)	N21—C26—C25	120.57 (15)
N11—C16—H16	119.6	N21—C26—H26	119.7
C15—C16—H16	119.6	C25—C26—H26	119.7
O17—C17—N117	126.59 (14)	O27—C27—N217	127.25 (14)
O17—C17—C12	119.57 (15)	O27—C27—C22	118.99 (14)
N117—C17—C12	113.84 (14)	N217—C27—C22	113.76 (14)
C17—N117—C111	125.31 (14)	C27—N217—C211	126.76 (14)
C17—N117—H117	118.7	C27—N217—H217	118.8
C111—N117—H117	115.7	C211—N217—H217	114.4
N117—C111—C116	116.86 (15)	N217—C211—C212	121.26 (15)
N117—C111—C112	120.46 (14)	N217—C211—C216	116.89 (14)
C116—C111—C112	122.64 (14)	C212—C211—C216	121.84 (14)
C113—C112—C111	116.95 (15)	C213—C212—C211	116.53 (15)
C113—C112—H112	121.5	C213—C212—H212	121.7
C111—C112—H112	121.5	C211—C212—H212	121.7
C112—C113—C114	121.53 (16)	C212—C213—C214	122.70 (15)
C112—C113—Cl11	116.66 (13)	C212—C213—Cl21	116.63 (13)
C114—C113—Cl11	121.81 (12)	C214—C213—Cl21	120.67 (12)
C113—C114—C115	120.57 (15)	C215—C214—C213	119.70 (15)
C113—C114—H114	119.7	C215—C214—H214	120.2
C115—C114—H114	119.7	C213—C214—H214	120.2
C116—C115—C114	119.65 (16)	C216—C215—C214	119.60 (17)
C116—C115—H115	120.2	C216—C215—H215	120.2
C114—C115—H115	120.2	C214—C215—H215	120.2
C115—C116—C111	118.66 (16)	C215—C216—C211	119.61 (16)
C115—C116—H116	120.7	C215—C216—H216	120.2
C111—C116—H116	120.7	C211—C216—H216	120.2
C16—N11—C12—C13	−0.7 (2)	C26—N21—C22—C23	−0.3 (2)
C16—N11—C12—C17	179.22 (15)	C26—N21—C22—C27	178.01 (15)
N11—C12—C13—N14	1.0 (3)	N21—C22—C23—N24	2.7 (3)
C17—C12—C13—N14	−178.90 (15)	C27—C22—C23—N24	−175.68 (15)
C12—C13—N14—C15	−0.4 (2)	C22—C23—N24—C25	−2.5 (2)
C13—N14—C15—C16	−0.5 (3)	C23—N24—C25—C26	0.4 (3)
C12—N11—C16—C15	−0.2 (2)	C22—N21—C26—C25	−1.8 (2)
N14—C15—C16—N11	0.8 (3)	N24—C25—C26—N21	1.9 (3)
N11—C12—C17—O17	−176.18 (16)	N21—C22—C27—O27	−176.63 (15)
C13—C12—C17—O17	3.7 (2)	C23—C22—C27—O27	1.8 (2)
N11—C12—C17—N117	4.1 (2)	N21—C22—C27—N217	3.0 (2)
C13—C12—C17—N117	−176.02 (15)	C23—C22—C27—N217	−178.51 (15)
O17—C17—N117—C111	−1.2 (3)	O27—C27—N217—C211	0.2 (3)
C12—C17—N117—C111	178.55 (15)	C22—C27—N217—C211	−179.46 (15)
C17—N117—C111—C116	152.58 (16)	C27—N217—C211—C212	−9.5 (3)
C17—N117—C111—C112	−29.5 (2)	C27—N217—C211—C216	170.85 (16)
N117—C111—C112—C113	−178.27 (15)	N217—C211—C212—C213	−179.58 (15)
C116—C111—C112—C113	−0.5 (2)	C216—C211—C212—C213	0.0 (2)
C111—C112—C113—C114	−0.5 (2)	C211—C212—C213—C214	1.1 (2)
C111—C112—C113—Cl11	179.14 (12)	C211—C212—C213—Cl21	−178.61 (12)
C112—C113—C114—C115	0.9 (3)	C212—C213—C214—C215	−1.2 (3)
Cl11—C113—C114—C115	−178.66 (13)	Cl21—C213—C214—C215	178.47 (14)
C113—C114—C115—C116	−0.4 (3)	C213—C214—C215—C216	0.1 (3)
C114—C115—C116—C111	−0.5 (2)	C214—C215—C216—C211	1.0 (3)
N117—C111—C116—C115	178.87 (15)	N217—C211—C216—C215	178.54 (16)
C112—C111—C116—C115	1.0 (2)	C212—C211—C216—C215	−1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N117—H117···N11	0.87	2.24	2.6339 (19)	108
N217—H217···N21	0.87	2.24	2.6368 (18)	108
N117—H117···N24^i	0.87	2.43	3.2248 (19)	153
N217—H217···N14	0.87	2.48	3.2954 (19)	156
C23—H23···N11^ii	0.95	2.54	3.221 (2)	129
C216—H216···N14	0.95	2.52	3.302 (2)	140

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

(XIII) N-(4-chlorophenyl)pyrazinecarboxamide

Crystal data

C11H8ClN3O	Z = 2
Mr = 233.65	F(000) = 240
Triclinic, P1	Dx = 1.552 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8636 (3) Å	Cell parameters from 2307 reflections
b = 7.2433 (5) Å	θ = 3.1–27.7°
c = 13.1459 (9) Å	µ = 0.36 mm^−1
α = 100.854 (3)°	T = 120 K
β = 97.750 (4)°	Lath, colourless
γ = 110.783 (4)°	0.26 × 0.05 × 0.02 mm
V = 500.14 (6) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	2307 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 9.091 pixels mm^-1	θmax = 27.7°, θmin = 3.1°
ϕ & ω scans	h = −7→7
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −9→9
Tmin = 0.944, Tmax = 0.993	l = −17→17
10153 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0384P)^2 + 0.2405P] where P = (Fo^2 + 2Fc^2)/3
2307 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2103 (3)	−0.0323 (2)	0.23472 (12)	0.0214 (4)
C2	0.4562 (3)	0.0284 (3)	0.26868 (14)	0.0178 (4)
C3	0.6058 (4)	−0.0164 (3)	0.20246 (15)	0.0210 (4)
N4	0.5139 (3)	−0.1211 (2)	0.10086 (12)	0.0228 (4)
C5	0.2681 (4)	−0.1807 (3)	0.06706 (15)	0.0234 (4)
C6	0.1172 (4)	−0.1373 (3)	0.13307 (15)	0.0234 (4)
C7	0.5768 (3)	0.1475 (3)	0.38171 (14)	0.0181 (4)
O7	0.8023 (3)	0.2029 (2)	0.41436 (10)	0.0242 (3)
N17	0.4168 (3)	0.1842 (2)	0.44006 (12)	0.0199 (4)
C11	0.4719 (4)	0.2914 (3)	0.54754 (14)	0.0185 (4)
C12	0.7132 (4)	0.4095 (3)	0.60639 (15)	0.0212 (4)
C13	0.7504 (4)	0.5134 (3)	0.71184 (15)	0.0222 (4)
C14	0.5475 (4)	0.4983 (3)	0.75752 (14)	0.0201 (4)
Cl14	0.59225 (10)	0.62828 (8)	0.88903 (4)	0.02569 (16)
C15	0.3069 (4)	0.3822 (3)	0.69922 (14)	0.0220 (4)
C16	0.2694 (4)	0.2794 (3)	0.59435 (14)	0.0207 (4)
H3	0.7801	0.0293	0.2306	0.025*
H5	0.1932	−0.2556	−0.0047	0.028*
H6	−0.0573	−0.1837	0.1051	0.028*
H17	0.2617	0.1334	0.4032	0.024*
H12	0.8523	0.4195	0.5749	0.025*
H13	0.9152	0.5946	0.7523	0.027*
H15	0.1681	0.3729	0.7308	0.026*
H16	0.1041	0.2000	0.5540	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0208 (9)	0.0244 (9)	0.0178 (8)	0.0087 (7)	0.0032 (6)	0.0037 (7)
C2	0.0209 (10)	0.0170 (9)	0.0151 (9)	0.0072 (8)	0.0021 (7)	0.0049 (7)
C3	0.0212 (10)	0.0224 (10)	0.0205 (10)	0.0102 (8)	0.0035 (8)	0.0057 (8)
N4	0.0255 (9)	0.0252 (9)	0.0172 (8)	0.0101 (7)	0.0041 (7)	0.0038 (7)
C5	0.0269 (11)	0.0255 (11)	0.0156 (9)	0.0100 (9)	0.0027 (8)	0.0017 (8)
C6	0.0202 (11)	0.0294 (11)	0.0176 (10)	0.0086 (9)	0.0023 (8)	0.0023 (8)
C7	0.0207 (11)	0.0179 (9)	0.0156 (9)	0.0078 (8)	0.0030 (7)	0.0046 (7)
O7	0.0213 (8)	0.0296 (8)	0.0187 (7)	0.0094 (6)	0.0022 (6)	0.0018 (6)
N17	0.0209 (9)	0.0227 (9)	0.0141 (8)	0.0085 (7)	0.0016 (6)	0.0016 (6)
C11	0.0237 (10)	0.0188 (10)	0.0146 (9)	0.0102 (8)	0.0027 (7)	0.0050 (7)
C12	0.0221 (11)	0.0220 (10)	0.0197 (10)	0.0087 (8)	0.0066 (8)	0.0043 (8)
C13	0.0230 (11)	0.0202 (10)	0.0192 (10)	0.0070 (8)	0.0014 (8)	0.0010 (8)
C14	0.0288 (11)	0.0189 (10)	0.0127 (9)	0.0104 (8)	0.0023 (8)	0.0034 (7)
Cl14	0.0332 (3)	0.0284 (3)	0.0140 (2)	0.0129 (2)	0.00397 (19)	0.00110 (18)
C15	0.0258 (11)	0.0267 (11)	0.0166 (9)	0.0130 (9)	0.0060 (8)	0.0064 (8)
C16	0.0197 (10)	0.0244 (10)	0.0173 (9)	0.0091 (8)	0.0014 (7)	0.0043 (8)

Geometric parameters (Å, º)

N1—C2	1.332 (2)	N17—H17	0.88
N1—C6	1.337 (2)	C11—C12	1.389 (3)
C2—C3	1.391 (3)	C11—C16	1.392 (3)
C2—C7	1.501 (2)	C12—C13	1.394 (3)
C3—N4	1.336 (2)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.383 (3)
N4—C5	1.332 (3)	C13—H13	0.95
C5—C6	1.392 (3)	C14—C15	1.382 (3)
C5—H5	0.95	C14—Cl14	1.7416 (18)
C6—H6	0.95	C15—C16	1.385 (3)
C7—O7	1.224 (2)	C15—H15	0.95
C7—N17	1.354 (2)	C16—H16	0.95
N17—C11	1.411 (2)
C2—N1—C6	115.85 (16)	C11—N17—H17	119.4
N1—C2—C3	121.89 (17)	C12—C11—C16	119.55 (17)
N1—C2—C7	119.44 (16)	C12—C11—N17	123.54 (17)
C3—C2—C7	118.67 (17)	C16—C11—N17	116.89 (17)
N4—C3—C2	122.53 (18)	C11—C12—C13	119.75 (18)
N4—C3—H3	118.7	C11—C12—H12	120.1
C2—C3—H3	118.7	C13—C12—H12	120.1
C5—N4—C3	115.41 (16)	C14—C13—C12	120.01 (18)
N4—C5—C6	122.34 (18)	C14—C13—H13	120.0
N4—C5—H5	118.8	C12—C13—H13	120.0
C6—C5—H5	118.8	C15—C14—C13	120.54 (17)
N1—C6—C5	121.97 (18)	C15—C14—Cl14	119.14 (15)
N1—C6—H6	119.0	C13—C14—Cl14	120.32 (15)
C5—C6—H6	119.0	C14—C15—C16	119.55 (18)
O7—C7—N17	125.28 (17)	C14—C15—H15	120.2
O7—C7—C2	120.22 (16)	C16—C15—H15	120.2
N17—C7—C2	114.50 (16)	C15—C16—C11	120.60 (18)
C7—N17—C11	128.08 (16)	C15—C16—H16	119.7
C7—N17—H17	112.6	C11—C16—H16	119.7
C6—N1—C2—C3	−0.5 (3)	C2—C7—N17—C11	−179.78 (16)
C6—N1—C2—C7	179.91 (16)	C7—N17—C11—C12	12.0 (3)
N1—C2—C3—N4	0.5 (3)	C7—N17—C11—C16	−169.58 (17)
C7—C2—C3—N4	−179.83 (16)	C16—C11—C12—C13	0.5 (3)
C2—C3—N4—C5	−0.2 (3)	N17—C11—C12—C13	178.89 (17)
C3—N4—C5—C6	−0.1 (3)	C11—C12—C13—C14	0.2 (3)
C2—N1—C6—C5	0.1 (3)	C12—C13—C14—C15	−0.6 (3)
N4—C5—C6—N1	0.2 (3)	C12—C13—C14—Cl14	−179.76 (14)
N1—C2—C7—O7	179.41 (17)	C13—C14—C15—C16	0.4 (3)
C3—C2—C7—O7	−0.2 (3)	Cl14—C14—C15—C16	179.55 (14)
N1—C2—C7—N17	−0.5 (2)	C14—C15—C16—C11	0.3 (3)
C3—C2—C7—N17	179.87 (16)	C12—C11—C16—C15	−0.7 (3)
O7—C7—N17—C11	0.3 (3)	N17—C11—C16—C15	−179.22 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.24	2.718 (2)	114
C16—H16···O7^i	0.95	2.38	3.176 (3)	141

Symmetry code: (i) x−1, y, z.

(XIV) N-(2-methoxyphenyl)pyrazinecarboxamide

Crystal data

C12H11N3O2	F(000) = 960
Mr = 229.24	Dx = 1.390 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2861 reflections
a = 14.1667 (4) Å	θ = 2.9–27.5°
b = 20.7513 (6) Å	µ = 0.10 mm^−1
c = 7.4516 (3) Å	T = 120 K
V = 2190.60 (12) Å^3	Lath, colourless
Z = 8	0.38 × 0.36 × 0.10 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	2509 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ϕ & ω scans	h = −16→18
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −23→26
Tmin = 0.984, Tmax = 0.990	l = −9→9
16739 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.185P] where P = (Fo^2 + 2Fc^2)/3
2509 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.69003 (7)	0.41030 (5)	0.65765 (14)	0.0228 (3)
C2	0.60024 (8)	0.42957 (6)	0.67454 (17)	0.0195 (3)
C3	0.56874 (9)	0.46232 (6)	0.82543 (17)	0.0234 (3)
N4	0.62604 (8)	0.47597 (5)	0.96319 (15)	0.0267 (3)
C5	0.71533 (9)	0.45650 (6)	0.94503 (18)	0.0263 (3)
C6	0.74751 (9)	0.42445 (6)	0.79433 (18)	0.0253 (3)
C7	0.53344 (8)	0.41405 (6)	0.52352 (17)	0.0206 (3)
O7	0.44927 (6)	0.42775 (4)	0.53183 (12)	0.0288 (2)
N17	0.57611 (7)	0.38381 (5)	0.38501 (14)	0.0221 (3)
C11	0.53633 (8)	0.35940 (6)	0.22667 (17)	0.0198 (3)
C12	0.59737 (8)	0.32344 (6)	0.11608 (17)	0.0205 (3)
O12	0.68797 (6)	0.31795 (4)	0.18028 (12)	0.0248 (2)
C121	0.75182 (9)	0.27901 (7)	0.08006 (19)	0.0320 (4)
C13	0.56525 (9)	0.29700 (6)	−0.04278 (18)	0.0244 (3)
C14	0.47168 (9)	0.30661 (6)	−0.09400 (19)	0.0272 (3)
C15	0.41162 (9)	0.34185 (6)	0.01372 (18)	0.0264 (3)
C16	0.44337 (8)	0.36814 (6)	0.17428 (18)	0.0228 (3)
H3	0.5046	0.4755	0.8312	0.028*
H5	0.7586	0.4650	1.0396	0.032*
H6	0.8120	0.4122	0.7877	0.030*
H17	0.6366	0.3768	0.4035	0.026*
H12A	0.7598	0.2973	−0.0402	0.048*
H12B	0.7265	0.2352	0.0703	0.048*
H12C	0.8130	0.2778	0.1412	0.048*
H13	0.6066	0.2725	−0.1164	0.029*
H14	0.4492	0.2888	−0.2034	0.033*
H15	0.3480	0.3482	−0.0222	0.032*
H16	0.4014	0.3921	0.2480	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0168 (6)	0.0272 (6)	0.0244 (6)	0.0004 (4)	0.0002 (4)	−0.0004 (5)
C2	0.0177 (6)	0.0188 (6)	0.0220 (7)	−0.0008 (5)	0.0020 (5)	0.0021 (5)
C3	0.0225 (7)	0.0221 (6)	0.0255 (7)	0.0015 (5)	0.0024 (5)	−0.0003 (6)
N4	0.0283 (7)	0.0257 (6)	0.0262 (7)	0.0015 (5)	0.0001 (5)	−0.0030 (5)
C5	0.0275 (7)	0.0253 (7)	0.0261 (7)	−0.0013 (6)	−0.0030 (6)	−0.0020 (6)
C6	0.0191 (7)	0.0292 (7)	0.0276 (8)	0.0004 (5)	−0.0016 (5)	0.0002 (6)
C7	0.0183 (6)	0.0198 (6)	0.0237 (7)	0.0000 (5)	0.0032 (5)	0.0021 (5)
O7	0.0159 (5)	0.0403 (6)	0.0300 (6)	0.0032 (4)	0.0015 (4)	−0.0032 (4)
N17	0.0150 (5)	0.0279 (6)	0.0233 (6)	0.0029 (4)	−0.0018 (4)	−0.0034 (5)
C11	0.0213 (6)	0.0184 (6)	0.0198 (7)	−0.0021 (5)	−0.0013 (5)	0.0021 (5)
C12	0.0180 (6)	0.0191 (6)	0.0245 (7)	−0.0004 (5)	−0.0018 (5)	0.0034 (5)
O12	0.0181 (5)	0.0309 (5)	0.0254 (5)	0.0065 (4)	−0.0013 (4)	−0.0052 (4)
C121	0.0254 (8)	0.0360 (8)	0.0345 (8)	0.0085 (6)	0.0012 (6)	−0.0079 (7)
C13	0.0270 (7)	0.0218 (6)	0.0245 (7)	−0.0016 (5)	0.0014 (6)	−0.0017 (6)
C14	0.0295 (8)	0.0276 (7)	0.0246 (7)	−0.0073 (6)	−0.0058 (6)	0.0002 (6)
C15	0.0207 (7)	0.0268 (7)	0.0316 (8)	−0.0040 (5)	−0.0069 (6)	0.0050 (6)
C16	0.0197 (7)	0.0215 (6)	0.0273 (7)	−0.0008 (5)	−0.0002 (5)	0.0018 (6)

Geometric parameters (Å, º)

N1—C6	1.3366 (16)	C11—C12	1.4083 (17)
N1—C2	1.3393 (15)	C12—O12	1.3745 (14)
C2—C3	1.3875 (18)	C12—C13	1.3818 (18)
C2—C7	1.5052 (17)	O12—C121	1.4244 (15)
C3—N4	1.3390 (16)	C121—H12A	0.98
C3—H3	0.95	C121—H12B	0.98
N4—C5	1.3348 (17)	C121—H12C	0.98
C5—C6	1.3824 (18)	C13—C14	1.3937 (18)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—C15	1.3794 (19)
C7—O7	1.2274 (14)	C14—H14	0.95
C7—N17	1.3507 (16)	C15—C16	1.3897 (19)
N17—C11	1.4023 (16)	C15—H15	0.95
N17—H17	0.8799	C16—H16	0.95
C11—C16	1.3856 (17)
C6—N1—C2	116.19 (11)	O12—C12—C13	124.94 (11)
N1—C2—C3	121.86 (12)	O12—C12—C11	114.43 (11)
N1—C2—C7	117.58 (11)	C13—C12—C11	120.62 (11)
C3—C2—C7	120.56 (11)	C12—O12—C121	117.23 (10)
N4—C3—C2	121.99 (12)	O12—C121—H12A	109.5
N4—C3—H3	119.0	O12—C121—H12B	109.5
C2—C3—H3	119.0	H12A—C121—H12B	109.5
C5—N4—C3	115.65 (11)	O12—C121—H12C	109.5
N4—C5—C6	122.71 (12)	H12A—C121—H12C	109.5
N4—C5—H5	118.6	H12B—C121—H12C	109.5
C6—C5—H5	118.6	C12—C13—C14	119.40 (12)
N1—C6—C5	121.59 (12)	C12—C13—H13	120.3
N1—C6—H6	119.2	C14—C13—H13	120.3
C5—C6—H6	119.2	C15—C14—C13	120.21 (12)
O7—C7—N17	125.52 (12)	C15—C14—H14	119.9
O7—C7—C2	121.57 (11)	C13—C14—H14	119.9
N17—C7—C2	112.91 (10)	C14—C15—C16	120.63 (12)
C7—N17—C11	129.12 (11)	C14—C15—H15	119.7
C7—N17—H17	113.1	C16—C15—H15	119.7
C11—N17—H17	117.6	C11—C16—C15	119.92 (12)
C16—C11—N17	124.87 (11)	C11—C16—H16	120.0
C16—C11—C12	119.22 (12)	C15—C16—H16	120.0
N17—C11—C12	115.91 (11)
C6—N1—C2—C3	−0.04 (17)	C7—N17—C11—C12	−172.77 (12)
C6—N1—C2—C7	−179.63 (10)	C16—C11—C12—O12	179.77 (10)
N1—C2—C3—N4	−0.62 (19)	N17—C11—C12—O12	−0.36 (15)
C7—C2—C3—N4	178.96 (11)	C16—C11—C12—C13	−0.11 (18)
C2—C3—N4—C5	0.53 (18)	N17—C11—C12—C13	179.76 (10)
C3—N4—C5—C6	0.18 (18)	C13—C12—O12—C121	−3.71 (17)
C2—N1—C6—C5	0.74 (18)	C11—C12—O12—C121	176.42 (11)
N4—C5—C6—N1	−0.8 (2)	O12—C12—C13—C14	−179.35 (11)
N1—C2—C7—O7	177.05 (11)	C11—C12—C13—C14	0.52 (18)
C3—C2—C7—O7	−2.55 (18)	C12—C13—C14—C15	−0.44 (19)
N1—C2—C7—N17	−2.27 (15)	C13—C14—C15—C16	−0.04 (19)
C3—C2—C7—N17	178.14 (11)	N17—C11—C16—C15	179.77 (11)
O7—C7—N17—C11	−2.7 (2)	C12—C11—C16—C15	−0.37 (18)
C2—C7—N17—C11	176.63 (11)	C14—C15—C16—C11	0.45 (19)
C7—N17—C11—C16	7.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.15	2.6522 (15)	115
C6—H6···O7^i	0.95	2.39	3.1389 (16)	136

Symmetry code: (i) x+1/2, y, −z+3/2.

(XV) N-(3-methoxyphenyl)pyrazinecarboxamide

Crystal data

C12H11N3O2·H2O	F(000) = 520
Mr = 247.25	Dx = 1.466 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2566 reflections
a = 6.9386 (2) Å	θ = 3.0–27.6°
b = 8.5820 (3) Å	µ = 0.11 mm^−1
c = 19.0670 (6) Å	T = 120 K
β = 99.394 (2)°	Needle, orange
V = 1120.16 (6) Å^3	0.48 × 0.08 × 0.06 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2566 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.0°
ϕ & ω scans	h = −8→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −11→11
Tmin = 0.961, Tmax = 0.994	l = −24→24
14126 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 0.5866P] where P = (Fo^2 + 2Fc^2)/3
2566 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.30896 (17)	0.39314 (14)	0.64460 (6)	0.0177 (3)
C2	0.31046 (19)	0.30844 (16)	0.58592 (7)	0.0162 (3)
C7	0.2614 (2)	0.38659 (16)	0.51460 (7)	0.0167 (3)
O7	0.22766 (15)	0.30662 (12)	0.46033 (5)	0.0221 (3)
N17	0.25891 (17)	0.54324 (13)	0.51678 (6)	0.0173 (3)
C11	0.2134 (2)	0.64761 (16)	0.45887 (7)	0.0164 (3)
C12	0.1988 (2)	0.60159 (16)	0.38847 (7)	0.0175 (3)
C13	0.1508 (2)	0.71141 (16)	0.33437 (7)	0.0175 (3)
O13	0.13674 (16)	0.65234 (12)	0.26700 (5)	0.0223 (3)
C131	0.0901 (2)	0.75928 (18)	0.20898 (7)	0.0241 (3)
C14	0.1202 (2)	0.86662 (17)	0.35002 (7)	0.0189 (3)
C15	0.1375 (2)	0.91068 (17)	0.42109 (7)	0.0199 (3)
C16	0.1825 (2)	0.80363 (16)	0.47530 (7)	0.0186 (3)
C3	0.3538 (2)	0.15038 (16)	0.58865 (7)	0.0186 (3)
N4	0.39377 (18)	0.07316 (14)	0.65020 (6)	0.0200 (3)
C5	0.3889 (2)	0.15723 (17)	0.70895 (7)	0.0199 (3)
C6	0.3484 (2)	0.31584 (17)	0.70586 (7)	0.0189 (3)
O1	0.49037 (16)	0.75125 (12)	0.62675 (5)	0.0251 (3)
H17	0.2890	0.5859	0.5591	0.021*
H12	0.2213	0.4961	0.3771	0.021*
H13A	0.1917	0.8394	0.2121	0.036*
H13B	−0.0361	0.8086	0.2113	0.036*
H13C	0.0828	0.7029	0.1639	0.036*
H14	0.0881	0.9411	0.3131	0.023*
H15	0.1178	1.0167	0.4325	0.024*
H16	0.1925	0.8356	0.5235	0.022*
H3	0.3550	0.0954	0.5455	0.022*
H5	0.4137	0.1072	0.7540	0.024*
H6	0.3488	0.3712	0.7490	0.023*
H1A	0.4705	0.8523	0.6361	0.038*
H1B	0.5864	0.7507	0.6001	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0192 (6)	0.0163 (6)	0.0176 (6)	−0.0006 (4)	0.0027 (5)	−0.0006 (4)
C2	0.0145 (6)	0.0168 (7)	0.0170 (7)	−0.0013 (5)	0.0014 (5)	−0.0003 (5)
C7	0.0170 (7)	0.0160 (7)	0.0171 (7)	−0.0004 (5)	0.0031 (5)	−0.0005 (5)
O7	0.0317 (6)	0.0179 (5)	0.0164 (5)	−0.0021 (4)	0.0025 (4)	−0.0019 (4)
N17	0.0229 (6)	0.0150 (6)	0.0133 (6)	−0.0006 (5)	0.0009 (4)	−0.0011 (4)
C11	0.0161 (7)	0.0163 (7)	0.0164 (7)	−0.0014 (5)	0.0013 (5)	0.0014 (5)
C12	0.0199 (7)	0.0149 (7)	0.0175 (7)	0.0002 (5)	0.0020 (5)	−0.0008 (5)
C13	0.0170 (7)	0.0200 (7)	0.0150 (7)	−0.0023 (5)	0.0017 (5)	−0.0008 (5)
O13	0.0339 (6)	0.0186 (5)	0.0138 (5)	−0.0007 (4)	0.0018 (4)	0.0004 (4)
C131	0.0323 (9)	0.0238 (8)	0.0154 (7)	−0.0025 (6)	0.0018 (6)	0.0043 (6)
C14	0.0187 (7)	0.0182 (7)	0.0195 (7)	−0.0006 (5)	0.0023 (5)	0.0034 (5)
C15	0.0212 (7)	0.0154 (7)	0.0228 (7)	0.0005 (5)	0.0028 (6)	−0.0008 (5)
C16	0.0204 (7)	0.0191 (7)	0.0162 (7)	−0.0001 (5)	0.0027 (5)	−0.0019 (5)
C3	0.0192 (7)	0.0172 (7)	0.0193 (7)	−0.0006 (5)	0.0024 (5)	−0.0011 (5)
N4	0.0215 (6)	0.0167 (6)	0.0213 (6)	0.0006 (5)	0.0023 (5)	0.0012 (5)
C5	0.0205 (7)	0.0211 (7)	0.0176 (7)	0.0005 (6)	0.0015 (5)	0.0031 (6)
C6	0.0207 (7)	0.0198 (7)	0.0161 (7)	−0.0015 (5)	0.0029 (5)	−0.0022 (5)
O1	0.0337 (6)	0.0194 (5)	0.0222 (5)	0.0016 (4)	0.0047 (4)	−0.0022 (4)

Geometric parameters (Å, º)

N1—C6	1.3323 (18)	C131—H13B	0.98
N1—C2	1.3357 (17)	C131—H13C	0.98
C2—C3	1.3885 (19)	C14—C15	1.393 (2)
C2—C7	1.5046 (18)	C14—H14	0.95
C7—O7	1.2319 (16)	C15—C16	1.380 (2)
C7—N17	1.3452 (18)	C15—H15	0.95
N17—C11	1.4167 (17)	C16—H16	0.95
N17—H17	0.88	C3—N4	1.3369 (18)
C11—C12	1.3870 (19)	C3—H3	0.95
C11—C16	1.3996 (19)	N4—C5	1.3375 (18)
C12—C13	1.3968 (19)	C5—C6	1.389 (2)
C12—H12	0.95	C5—H5	0.95
C13—O13	1.3694 (16)	C6—H6	0.95
C13—C14	1.389 (2)	O1—H1A	0.9005
O13—C131	1.4331 (16)	O1—H1B	0.9022
C131—H13A	0.98
C6—N1—C2	115.78 (12)	O13—C131—H13C	109.5
N1—C2—C3	122.11 (13)	H13A—C131—H13C	109.5
N1—C2—C7	118.88 (12)	H13B—C131—H13C	109.5
C3—C2—C7	119.01 (12)	C13—C14—C15	118.52 (13)
O7—C7—N17	125.52 (13)	C13—C14—H14	120.7
O7—C7—C2	119.65 (12)	C15—C14—H14	120.7
N17—C7—C2	114.82 (12)	C16—C15—C14	121.39 (13)
C7—N17—C11	127.60 (12)	C16—C15—H15	119.3
C7—N17—H17	116.2	C14—C15—H15	119.3
C11—N17—H17	116.2	C15—C16—C11	119.57 (13)
C12—C11—C16	119.95 (13)	C15—C16—H16	120.2
C12—C11—N17	123.10 (13)	C11—C16—H16	120.2
C16—C11—N17	116.95 (12)	N4—C3—C2	121.99 (13)
C11—C12—C13	119.57 (13)	N4—C3—H3	119.0
C11—C12—H12	120.2	C2—C3—H3	119.0
C13—C12—H12	120.2	C3—N4—C5	115.97 (12)
O13—C13—C14	124.51 (12)	N4—C5—C6	121.71 (13)
O13—C13—C12	114.51 (12)	N4—C5—H5	119.1
C14—C13—C12	120.99 (13)	C6—C5—H5	119.1
C13—O13—C131	117.36 (11)	N1—C6—C5	122.42 (13)
O13—C131—H13A	109.5	N1—C6—H6	118.8
O13—C131—H13B	109.5	C5—C6—H6	118.8
H13A—C131—H13B	109.5	H1A—O1—H1B	105.5
C6—N1—C2—C3	−1.11 (19)	C14—C13—O13—C131	1.0 (2)
C6—N1—C2—C7	178.20 (12)	C12—C13—O13—C131	−179.28 (12)
N1—C2—C7—O7	−166.99 (13)	O13—C13—C14—C15	179.39 (13)
C3—C2—C7—O7	12.3 (2)	C12—C13—C14—C15	−0.3 (2)
N1—C2—C7—N17	13.01 (18)	C13—C14—C15—C16	−0.5 (2)
C3—C2—C7—N17	−167.66 (13)	C14—C15—C16—C11	0.6 (2)
O7—C7—N17—C11	1.6 (2)	C12—C11—C16—C15	0.0 (2)
C2—C7—N17—C11	−178.37 (12)	N17—C11—C16—C15	−179.90 (12)
C7—N17—C11—C12	−12.4 (2)	N1—C2—C3—N4	1.0 (2)
C7—N17—C11—C16	167.58 (14)	C7—C2—C3—N4	−178.31 (12)
C16—C11—C12—C13	−0.8 (2)	C2—C3—N4—C5	0.2 (2)
N17—C11—C12—C13	179.14 (12)	C3—N4—C5—C6	−1.2 (2)
C11—C12—C13—O13	−178.79 (12)	C2—N1—C6—C5	0.1 (2)
C11—C12—C13—C14	0.9 (2)	N4—C5—C6—N1	1.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.31	2.7283 (16)	109
N17—H17···O1	0.88	2.25	3.0105 (15)	145
O1—H1A···N4^i	0.90	2.00	2.8947 (16)	173
O1—H1B···O7^ii	0.90	1.93	2.8092 (15)	165

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

(XVII) N-(2-nitrophenyl)pyrazinecarboxamide?

Crystal data

C11H8N4O3	F(000) = 504
Mr = 244.21	Dx = 1.557 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2341 reflections
a = 3.6598 (2) Å	θ = 3.1–27.3°
b = 21.7123 (17) Å	µ = 0.12 mm^−1
c = 13.1158 (10) Å	T = 120 K
β = 91.281 (5)°	Lath, yellow
V = 1041.96 (13) Å^3	0.26 × 0.04 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2341 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1418 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
Detector resolution: 9.091 pixels mm^-1	θmax = 27.3°, θmin = 3.1°
ϕ & ω scans	h = −4→4
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −27→27
Tmin = 0.980, Tmax = 0.997	l = −16→16
12339 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0568P)^2 + 0.1342P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2341 reflections	Δρmax = 0.29 e Å^−3
164 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.1850 (5)	0.53464 (9)	0.88022 (16)	0.0241 (5)
C2	−0.0416 (6)	0.56080 (11)	0.79746 (19)	0.0218 (6)
C3	−0.0117 (6)	0.62421 (11)	0.7878 (2)	0.0248 (6)
N4	−0.1205 (5)	0.66273 (9)	0.86046 (17)	0.0284 (5)
C5	−0.2559 (6)	0.63660 (11)	0.9435 (2)	0.0272 (6)
C6	−0.2905 (6)	0.57313 (11)	0.95331 (19)	0.0260 (6)
C7	0.0926 (6)	0.51945 (11)	0.71441 (19)	0.0231 (6)
O7	0.2630 (5)	0.54106 (7)	0.64350 (13)	0.0290 (5)
N17	0.0104 (5)	0.45926 (8)	0.72852 (15)	0.0228 (5)
C11	0.0908 (6)	0.40893 (10)	0.66584 (19)	0.0206 (6)
C12	0.0410 (6)	0.34788 (11)	0.69925 (18)	0.0218 (6)
N12	−0.0980 (5)	0.33331 (10)	0.79989 (16)	0.0283 (5)
O121	−0.2605 (5)	0.37332 (8)	0.84866 (13)	0.0306 (5)
O122	−0.0514 (6)	0.28109 (9)	0.83390 (15)	0.0468 (6)
C13	0.1230 (6)	0.29763 (11)	0.63835 (19)	0.0255 (6)
C14	0.2538 (6)	0.30676 (12)	0.54240 (19)	0.0271 (6)
C15	0.3049 (6)	0.36632 (11)	0.5075 (2)	0.0253 (6)
C16	0.2267 (6)	0.41660 (11)	0.56828 (18)	0.0231 (6)
H3	0.0894	0.6408	0.7276	0.030*
H5	−0.3314	0.6622	0.9978	0.033*
H6	−0.3919	0.5567	1.0136	0.031*
H17	−0.1097	0.4490	0.7834	0.027*
H13	0.0886	0.2570	0.6632	0.031*
H14	0.3088	0.2726	0.5002	0.033*
H15	0.3950	0.3728	0.4410	0.030*
H16	0.2663	0.4570	0.5430	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0233 (11)	0.0242 (11)	0.0250 (13)	0.0015 (9)	0.0008 (9)	−0.0020 (10)
C2	0.0197 (12)	0.0211 (13)	0.0244 (14)	−0.0006 (10)	−0.0003 (10)	0.0012 (11)
C3	0.0267 (14)	0.0235 (14)	0.0242 (15)	−0.0013 (10)	0.0039 (11)	−0.0006 (11)
N4	0.0300 (12)	0.0235 (12)	0.0320 (14)	0.0012 (9)	0.0038 (10)	−0.0017 (10)
C5	0.0253 (14)	0.0256 (15)	0.0305 (16)	0.0019 (11)	−0.0011 (12)	−0.0046 (12)
C6	0.0262 (14)	0.0265 (15)	0.0255 (15)	−0.0010 (11)	0.0020 (11)	−0.0007 (12)
C7	0.0215 (13)	0.0224 (14)	0.0255 (15)	0.0009 (10)	0.0000 (11)	0.0022 (11)
O7	0.0350 (10)	0.0241 (10)	0.0283 (11)	−0.0029 (8)	0.0068 (8)	0.0017 (8)
N17	0.0288 (11)	0.0197 (11)	0.0202 (12)	−0.0007 (9)	0.0056 (9)	−0.0007 (9)
C11	0.0187 (12)	0.0209 (13)	0.0223 (14)	0.0004 (10)	−0.0018 (10)	−0.0016 (11)
C12	0.0230 (13)	0.0237 (14)	0.0188 (14)	−0.0022 (10)	0.0033 (10)	0.0015 (10)
N12	0.0343 (12)	0.0242 (12)	0.0264 (13)	−0.0044 (10)	0.0039 (10)	−0.0008 (10)
O121	0.0386 (11)	0.0283 (10)	0.0254 (11)	0.0011 (8)	0.0109 (8)	−0.0021 (8)
O122	0.0848 (16)	0.0226 (11)	0.0337 (12)	0.0048 (10)	0.0149 (11)	0.0097 (9)
C13	0.0272 (14)	0.0206 (14)	0.0288 (16)	−0.0018 (10)	0.0017 (11)	0.0013 (11)
C14	0.0273 (14)	0.0303 (15)	0.0239 (15)	0.0007 (11)	0.0031 (11)	−0.0053 (12)
C15	0.0242 (13)	0.0311 (15)	0.0207 (15)	−0.0013 (11)	0.0010 (11)	0.0001 (12)
C16	0.0268 (14)	0.0227 (14)	0.0196 (14)	−0.0019 (10)	−0.0004 (11)	0.0033 (11)

Geometric parameters (Å, º)

N1—C6	1.335 (3)	C11—C16	1.393 (3)
N1—C2	1.342 (3)	C11—C12	1.409 (3)
C2—C3	1.387 (3)	C12—C13	1.389 (3)
C2—C7	1.502 (3)	C12—N12	1.460 (3)
C3—N4	1.335 (3)	N12—O122	1.229 (3)
C3—H3	0.95	N12—O121	1.239 (3)
N4—C5	1.333 (3)	C13—C14	1.371 (3)
C5—C6	1.390 (3)	C13—H13	0.95
C5—H5	0.95	C14—C15	1.386 (3)
C6—H6	0.95	C14—H14	0.95
C7—O7	1.225 (3)	C15—C16	1.385 (3)
C7—N17	1.355 (3)	C15—H15	0.95
N17—C11	1.403 (3)	C16—H16	0.95
N17—H17	0.88
C6—N1—C2	116.1 (2)	C16—C11—C12	116.7 (2)
N1—C2—C3	121.8 (2)	N17—C11—C12	121.3 (2)
N1—C2—C7	118.3 (2)	C13—C12—C11	121.9 (2)
C3—C2—C7	120.0 (2)	C13—C12—N12	115.7 (2)
N4—C3—C2	122.1 (2)	C11—C12—N12	122.3 (2)
N4—C3—H3	118.9	O122—N12—O121	121.6 (2)
C2—C3—H3	118.9	O122—N12—C12	118.7 (2)
C5—N4—C3	116.0 (2)	O121—N12—C12	119.7 (2)
N4—C5—C6	122.3 (2)	C14—C13—C12	119.9 (2)
N4—C5—H5	118.9	C14—C13—H13	120.0
C6—C5—H5	118.9	C12—C13—H13	120.0
N1—C6—C5	121.7 (2)	C13—C14—C15	119.4 (2)
N1—C6—H6	119.1	C13—C14—H14	120.3
C5—C6—H6	119.1	C15—C14—H14	120.3
O7—C7—N17	126.3 (2)	C16—C15—C14	121.0 (2)
O7—C7—C2	120.1 (2)	C16—C15—H15	119.5
N17—C7—C2	113.6 (2)	C14—C15—H15	119.5
C7—N17—C11	128.4 (2)	C15—C16—C11	121.1 (2)
C7—N17—H17	118.2	C15—C16—H16	119.4
C11—N17—H17	113.4	C11—C16—H16	119.4
C16—C11—N17	121.9 (2)
C6—N1—C2—C3	−1.2 (3)	C16—C11—C12—C13	0.0 (3)
C6—N1—C2—C7	178.1 (2)	N17—C11—C12—C13	−179.4 (2)
N1—C2—C3—N4	0.6 (4)	C16—C11—C12—N12	179.8 (2)
C7—C2—C3—N4	−178.7 (2)	N17—C11—C12—N12	0.4 (3)
C2—C3—N4—C5	0.8 (3)	C13—C12—N12—O122	17.4 (3)
C3—N4—C5—C6	−1.5 (3)	C11—C12—N12—O122	−162.3 (2)
C2—N1—C6—C5	0.5 (3)	C13—C12—N12—O121	−162.2 (2)
N4—C5—C6—N1	0.9 (4)	C11—C12—N12—O121	18.0 (3)
N1—C2—C7—O7	−171.5 (2)	C11—C12—C13—C14	−0.5 (3)
C3—C2—C7—O7	7.8 (3)	N12—C12—C13—C14	179.7 (2)
N1—C2—C7—N17	7.6 (3)	C12—C13—C14—C15	0.4 (3)
C3—C2—C7—N17	−173.2 (2)	C13—C14—C15—C16	0.1 (3)
O7—C7—N17—C11	−1.6 (4)	C14—C15—C16—C11	−0.6 (3)
C2—C7—N17—C11	179.4 (2)	N17—C11—C16—C15	179.9 (2)
C7—N17—C11—C16	−10.2 (3)	C12—C11—C16—C15	0.5 (3)
C7—N17—C11—C12	169.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.27	2.686 (3)	109
N17—H17···O121	0.88	1.94	2.649 (3)	137
C14—H14···O122^i	0.95	2.54	3.422 (3)	155
C15—H15···O7^ii	0.95	2.52	3.257 (3)	134

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

(XX) N-(2,6-dimethylphenyl)pyrazinecarboxamide

Crystal data

C13H13N3O	F(000) = 480
Mr = 227.26	Dx = 1.269 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2723 reflections
a = 7.3977 (4) Å	θ = 3.3–27.5°
b = 10.7671 (5) Å	µ = 0.08 mm^−1
c = 15.2457 (4) Å	T = 120 K
β = 101.665 (3)°	Plate, colourless
V = 1189.27 (9) Å^3	0.48 × 0.16 × 0.05 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2723 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1775 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
ϕ & ω scans	h = −9→9
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −13→13
Tmin = 0.975, Tmax = 0.996	l = −19→18
16731 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0584P)^2 + 0.0716P] where P = (Fo^2 + 2Fc^2)/3
2723 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.30541 (17)	0.19694 (11)	0.33164 (7)	0.0259 (3)
N4	0.54067 (18)	0.38744 (12)	0.29754 (8)	0.0324 (3)
C2	0.3642 (2)	0.28716 (13)	0.39124 (9)	0.0234 (3)
C3	0.4802 (2)	0.38114 (14)	0.37436 (9)	0.0290 (4)
C5	0.4801 (2)	0.29751 (15)	0.23817 (10)	0.0297 (4)
C6	0.3645 (2)	0.20311 (14)	0.25479 (9)	0.0276 (4)
C7	0.3024 (2)	0.27995 (13)	0.47911 (9)	0.0256 (4)
O7	0.35933 (16)	0.35280 (10)	0.54026 (6)	0.0359 (3)
N17	0.18305 (17)	0.18683 (11)	0.48341 (7)	0.0272 (3)
C11	0.1104 (2)	0.15501 (13)	0.56050 (9)	0.0236 (3)
C12	−0.0109 (2)	0.23585 (15)	0.59085 (10)	0.0316 (4)
C121	−0.0657 (3)	0.35849 (17)	0.54624 (13)	0.0495 (5)
C13	−0.0815 (3)	0.19891 (18)	0.66440 (12)	0.0451 (5)
C14	−0.0382 (3)	0.0866 (2)	0.70520 (11)	0.0505 (6)
C15	0.0819 (3)	0.00792 (17)	0.67408 (10)	0.0420 (5)
C16	0.1593 (2)	0.04040 (14)	0.60114 (9)	0.0293 (4)
C161	0.2951 (2)	−0.04315 (15)	0.56941 (11)	0.0396 (4)
H3	0.5181	0.4430	0.4187	0.035*
H5	0.5180	0.2986	0.1822	0.036*
H6	0.3265	0.1413	0.2104	0.033*
H17	0.1597	0.1369	0.4368	0.033*
H12A	−0.1765	0.3896	0.5649	0.059*
H12B	−0.0913	0.3476	0.4811	0.059*
H12C	0.0352	0.4182	0.5636	0.059*
H13	−0.1622	0.2532	0.6871	0.054*
H14	−0.0907	0.0629	0.7547	0.061*
H15	0.1125	−0.0697	0.7029	0.050*
H16A	0.2604	−0.0526	0.5042	0.047*
H16B	0.2950	−0.1247	0.5979	0.047*
H16C	0.4189	−0.0068	0.5854	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0291 (8)	0.0273 (7)	0.0213 (6)	0.0009 (6)	0.0048 (5)	0.0005 (5)
N4	0.0356 (8)	0.0353 (8)	0.0280 (7)	−0.0033 (6)	0.0106 (6)	0.0040 (6)
C2	0.0259 (8)	0.0234 (8)	0.0203 (7)	0.0003 (6)	0.0033 (6)	0.0017 (5)
C3	0.0335 (9)	0.0284 (9)	0.0249 (8)	−0.0041 (7)	0.0055 (6)	0.0012 (6)
C5	0.0296 (9)	0.0376 (10)	0.0235 (8)	0.0050 (7)	0.0091 (6)	0.0051 (6)
C6	0.0299 (9)	0.0308 (9)	0.0215 (8)	0.0038 (7)	0.0034 (6)	−0.0010 (6)
C7	0.0312 (9)	0.0239 (8)	0.0213 (7)	−0.0025 (7)	0.0050 (6)	0.0008 (6)
O7	0.0505 (8)	0.0348 (7)	0.0236 (6)	−0.0170 (5)	0.0103 (5)	−0.0062 (5)
N17	0.0342 (8)	0.0270 (7)	0.0213 (6)	−0.0085 (6)	0.0078 (5)	−0.0034 (5)
C11	0.0234 (8)	0.0275 (8)	0.0195 (7)	−0.0063 (6)	0.0036 (6)	−0.0015 (6)
C12	0.0278 (9)	0.0334 (9)	0.0343 (8)	−0.0060 (7)	0.0074 (7)	−0.0103 (7)
C121	0.0450 (12)	0.0379 (11)	0.0646 (13)	0.0079 (9)	0.0088 (9)	−0.0098 (9)
C13	0.0403 (11)	0.0556 (12)	0.0454 (10)	−0.0189 (9)	0.0226 (8)	−0.0237 (9)
C14	0.0592 (13)	0.0665 (14)	0.0311 (9)	−0.0349 (11)	0.0220 (9)	−0.0125 (9)
C15	0.0509 (12)	0.0433 (11)	0.0284 (8)	−0.0222 (9)	−0.0001 (8)	0.0074 (7)
C16	0.0276 (9)	0.0307 (9)	0.0271 (8)	−0.0092 (7)	0.0000 (6)	0.0001 (6)
C161	0.0339 (10)	0.0292 (9)	0.0514 (10)	−0.0009 (8)	−0.0015 (8)	0.0015 (7)

Geometric parameters (Å, º)

N1—C6	1.3325 (18)	C12—C13	1.387 (2)
N1—C2	1.3412 (18)	C12—C121	1.503 (2)
N4—C3	1.3371 (18)	C121—H12A	0.98
N4—C5	1.339 (2)	C121—H12B	0.98
C2—C3	1.384 (2)	C121—H12C	0.98
C2—C7	1.5027 (19)	C13—C14	1.368 (3)
C3—H3	0.95	C13—H13	0.95
C5—C6	1.384 (2)	C14—C15	1.379 (3)
C5—H5	0.95	C14—H14	0.95
C6—H6	0.95	C15—C16	1.394 (2)
C7—O7	1.2260 (17)	C15—H15	0.95
C7—N17	1.3461 (19)	C16—C161	1.500 (2)
N17—C11	1.4293 (17)	C161—H16A	0.98
N17—H17	0.88	C161—H16B	0.98
C11—C12	1.394 (2)	C161—H16C	0.98
C11—C16	1.395 (2)
C6—N1—C2	116.13 (13)	C11—C12—C121	122.07 (14)
C3—N4—C5	115.45 (13)	C12—C121—H12A	109.5
N1—C2—C3	122.14 (13)	C12—C121—H12B	109.5
N1—C2—C7	116.81 (12)	H12A—C121—H12B	109.5
C3—C2—C7	121.04 (13)	C12—C121—H12C	109.5
N4—C3—C2	121.98 (14)	H12A—C121—H12C	109.5
N4—C3—H3	119.0	H12B—C121—H12C	109.5
C2—C3—H3	119.0	C14—C13—C12	121.96 (17)
N4—C5—C6	122.82 (13)	C14—C13—H13	119.0
N4—C5—H5	118.6	C12—C13—H13	119.0
C6—C5—H5	118.6	C13—C14—C15	119.60 (16)
N1—C6—C5	121.48 (14)	C13—C14—H14	120.2
N1—C6—H6	119.3	C15—C14—H14	120.2
C5—C6—H6	119.3	C14—C15—C16	121.15 (17)
O7—C7—N17	124.58 (13)	C14—C15—H15	119.4
O7—C7—C2	121.67 (13)	C16—C15—H15	119.4
N17—C7—C2	113.75 (12)	C15—C16—C11	117.69 (15)
C7—N17—C11	125.30 (12)	C15—C16—C161	121.11 (15)
C7—N17—H17	116.1	C11—C16—C161	121.17 (13)
C11—N17—H17	118.2	C16—C161—H16A	109.5
C12—C11—C16	122.08 (13)	C16—C161—H16B	109.5
C12—C11—N17	119.83 (13)	H16A—C161—H16B	109.5
C16—C11—N17	118.05 (13)	C16—C161—H16C	109.5
C13—C12—C11	117.50 (16)	H16A—C161—H16C	109.5
C13—C12—C121	120.43 (16)	H16B—C161—H16C	109.5
C6—N1—C2—C3	−0.3 (2)	C7—N17—C11—C16	−114.18 (16)
C6—N1—C2—C7	−178.65 (13)	C16—C11—C12—C13	0.6 (2)
C5—N4—C3—C2	0.6 (2)	N17—C11—C12—C13	178.20 (13)
N1—C2—C3—N4	−0.1 (2)	C16—C11—C12—C121	−179.09 (15)
C7—C2—C3—N4	178.26 (14)	N17—C11—C12—C121	−1.5 (2)
C3—N4—C5—C6	−0.8 (2)	C11—C12—C13—C14	−1.4 (2)
C2—N1—C6—C5	0.1 (2)	C121—C12—C13—C14	178.30 (17)
N4—C5—C6—N1	0.5 (2)	C12—C13—C14—C15	1.4 (3)
N1—C2—C7—O7	174.68 (14)	C13—C14—C15—C16	−0.5 (3)
C3—C2—C7—O7	−3.7 (2)	C14—C15—C16—C11	−0.2 (2)
N1—C2—C7—N17	−4.62 (19)	C14—C15—C16—C161	177.78 (15)
C3—C2—C7—N17	176.98 (13)	C12—C11—C16—C15	0.2 (2)
O7—C7—N17—C11	−2.8 (2)	N17—C11—C16—C15	−177.47 (13)
C2—C7—N17—C11	176.51 (13)	C12—C11—C16—C161	−177.80 (14)
C7—N17—C11—C12	68.1 (2)	N17—C11—C16—C161	4.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.20	2.6518 (16)	111
C3—H3···O7^i	0.95	2.41	3.2688 (18)	150

Symmetry code: (i) −x+1, −y+1, −z+1.

(XXI) N-(2,6-difluorophenyl)pyrazinecarboxamide

Crystal data

C11H7F2N3O	F(000) = 960
Mr = 235.20	Dx = 1.538 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2312 reflections
a = 9.8054 (4) Å	θ = 3.2–27.4°
b = 10.9355 (5) Å	µ = 0.13 mm^−1
c = 19.4805 (9) Å	T = 120 K
β = 103.474 (2)°	Plate, colourless
V = 2031.34 (16) Å^3	0.20 × 0.14 × 0.03 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	2312 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 9.091 pixels mm^-1	θmax = 27.4°, θmin = 3.2°
ϕ & ω scans	h = −12→12
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −14→13
Tmin = 0.984, Tmax = 0.996	l = −25→25
12350 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 1.574P] where P = (Fo^2 + 2Fc^2)/3
2312 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.21935 (14)	0.42042 (12)	0.25078 (7)	0.0243 (3)
C2	0.29661 (16)	0.31950 (14)	0.26687 (8)	0.0208 (3)
C3	0.26352 (17)	0.21169 (15)	0.22931 (9)	0.0231 (4)
N4	0.15035 (15)	0.20133 (13)	0.17608 (7)	0.0267 (3)
C5	0.07397 (18)	0.30302 (16)	0.15963 (9)	0.0284 (4)
C6	0.10848 (18)	0.41131 (16)	0.19603 (9)	0.0286 (4)
C7	0.42342 (16)	0.32238 (14)	0.32732 (8)	0.0208 (3)
O7	0.49267 (12)	0.22987 (10)	0.34594 (6)	0.0265 (3)
N17	0.45515 (14)	0.43359 (12)	0.35739 (7)	0.0225 (3)
C11	0.57736 (16)	0.45357 (14)	0.41093 (8)	0.0205 (3)
C12	0.60765 (17)	0.39043 (15)	0.47440 (9)	0.0233 (4)
F12	0.51227 (10)	0.30902 (9)	0.48657 (5)	0.0301 (3)
C13	0.72927 (18)	0.40791 (17)	0.52542 (9)	0.0284 (4)
C14	0.82308 (18)	0.49569 (17)	0.51386 (10)	0.0312 (4)
C15	0.79667 (18)	0.56423 (16)	0.45263 (10)	0.0296 (4)
C16	0.67495 (17)	0.54075 (15)	0.40266 (9)	0.0241 (4)
F16	0.64818 (10)	0.60453 (9)	0.34139 (5)	0.0329 (3)
H3	0.3233	0.1429	0.2418	0.028*
H5	−0.0068	0.3007	0.1216	0.034*
H6	0.0518	0.4814	0.1817	0.034*
H17	0.4065	0.4981	0.3390	0.027*
H13	0.7484	0.3608	0.5676	0.034*
H14	0.9073	0.5091	0.5487	0.037*
H15	0.8604	0.6255	0.4452	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0264 (7)	0.0191 (7)	0.0260 (8)	−0.0004 (6)	0.0034 (6)	0.0002 (6)
C2	0.0235 (8)	0.0183 (8)	0.0216 (8)	−0.0007 (6)	0.0076 (6)	0.0022 (6)
C3	0.0257 (8)	0.0196 (9)	0.0243 (8)	−0.0007 (7)	0.0067 (7)	0.0013 (7)
N4	0.0323 (8)	0.0226 (8)	0.0240 (7)	−0.0026 (6)	0.0038 (6)	−0.0004 (6)
C5	0.0297 (9)	0.0261 (9)	0.0253 (9)	−0.0029 (7)	−0.0017 (7)	0.0025 (7)
C6	0.0292 (9)	0.0236 (9)	0.0292 (9)	0.0011 (7)	−0.0007 (7)	0.0029 (7)
C7	0.0229 (8)	0.0187 (8)	0.0217 (8)	−0.0014 (7)	0.0071 (6)	0.0004 (6)
O7	0.0279 (6)	0.0208 (6)	0.0291 (7)	0.0037 (5)	0.0029 (5)	0.0003 (5)
N17	0.0235 (7)	0.0177 (7)	0.0241 (7)	0.0005 (5)	0.0014 (6)	0.0008 (6)
C11	0.0209 (8)	0.0175 (8)	0.0229 (8)	0.0005 (6)	0.0047 (6)	−0.0023 (6)
C12	0.0255 (8)	0.0190 (8)	0.0266 (9)	−0.0038 (7)	0.0089 (7)	−0.0020 (7)
F12	0.0326 (5)	0.0279 (6)	0.0300 (6)	−0.0089 (4)	0.0079 (4)	0.0042 (4)
C13	0.0307 (9)	0.0303 (10)	0.0228 (9)	−0.0005 (7)	0.0032 (7)	−0.0014 (7)
C14	0.0246 (9)	0.0351 (11)	0.0307 (10)	−0.0041 (8)	0.0000 (7)	−0.0085 (8)
C15	0.0252 (9)	0.0261 (10)	0.0381 (10)	−0.0082 (7)	0.0084 (8)	−0.0057 (8)
C16	0.0271 (8)	0.0193 (8)	0.0273 (9)	0.0019 (7)	0.0094 (7)	0.0013 (7)
F16	0.0354 (6)	0.0289 (6)	0.0360 (6)	−0.0018 (4)	0.0117 (5)	0.0101 (5)

Geometric parameters (Å, º)

N1—C2	1.334 (2)	N17—H17	0.88
N1—C6	1.338 (2)	C11—C16	1.386 (2)
C2—C3	1.386 (2)	C11—C12	1.387 (2)
C2—C7	1.500 (2)	C12—F12	1.3516 (18)
C3—N4	1.335 (2)	C12—C13	1.376 (2)
C3—H3	0.95	C13—C14	1.384 (3)
N4—C5	1.337 (2)	C13—H13	0.95
C5—C6	1.381 (2)	C14—C15	1.381 (3)
C5—H5	0.95	C14—H14	0.95
C6—H6	0.95	C15—C16	1.377 (2)
C7—O7	1.2254 (18)	C15—H15	0.95
C7—N17	1.354 (2)	C16—F16	1.3543 (19)
N17—C11	1.410 (2)
C2—N1—C6	115.93 (14)	C11—N17—H17	117.6
N1—C2—C3	121.98 (15)	C16—C11—C12	115.83 (14)
N1—C2—C7	119.24 (14)	C16—C11—N17	120.74 (14)
C3—C2—C7	118.79 (14)	C12—C11—N17	123.42 (14)
N4—C3—C2	122.16 (15)	F12—C12—C13	118.91 (15)
N4—C3—H3	118.9	F12—C12—C11	118.11 (14)
C2—C3—H3	118.9	C13—C12—C11	122.98 (15)
C3—N4—C5	115.67 (14)	C12—C13—C14	118.41 (16)
N4—C5—C6	122.23 (15)	C12—C13—H13	120.8
N4—C5—H5	118.9	C14—C13—H13	120.8
C6—C5—H5	118.9	C15—C14—C13	121.27 (16)
N1—C6—C5	121.98 (16)	C15—C14—H14	119.4
N1—C6—H6	119.0	C13—C14—H14	119.4
C5—C6—H6	119.0	C16—C15—C14	117.80 (16)
O7—C7—N17	123.90 (15)	C16—C15—H15	121.1
O7—C7—C2	121.05 (14)	C14—C15—H15	121.1
N17—C7—C2	115.04 (13)	F16—C16—C15	119.01 (15)
C7—N17—C11	121.94 (13)	F16—C16—C11	117.33 (14)
C7—N17—H17	119.7	C15—C16—C11	123.65 (16)
C6—N1—C2—C3	−0.3 (2)	C7—N17—C11—C12	−58.2 (2)
C6—N1—C2—C7	179.59 (14)	C16—C11—C12—F12	176.59 (14)
N1—C2—C3—N4	−1.9 (3)	N17—C11—C12—F12	−2.7 (2)
C7—C2—C3—N4	178.24 (14)	C16—C11—C12—C13	−2.8 (2)
C2—C3—N4—C5	2.4 (2)	N17—C11—C12—C13	177.93 (15)
C3—N4—C5—C6	−1.0 (3)	F12—C12—C13—C14	−176.93 (15)
C2—N1—C6—C5	1.7 (2)	C11—C12—C13—C14	2.4 (3)
N4—C5—C6—N1	−1.1 (3)	C12—C13—C14—C15	−0.3 (3)
N1—C2—C7—O7	176.18 (15)	C13—C14—C15—C16	−1.2 (3)
C3—C2—C7—O7	−3.9 (2)	C14—C15—C16—F16	−178.38 (15)
N1—C2—C7—N17	−5.2 (2)	C14—C15—C16—C11	0.8 (3)
C3—C2—C7—N17	174.67 (14)	C12—C11—C16—F16	−179.67 (14)
O7—C7—N17—C11	3.8 (2)	N17—C11—C16—F16	−0.4 (2)
C2—C7—N17—C11	−174.78 (13)	C12—C11—C16—C15	1.1 (2)
C7—N17—C11—C16	122.51 (17)	N17—C11—C16—C15	−179.59 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.36	2.7280 (19)	105
N17—H17···N4^i	0.88	2.29	3.1230 (19)	157
C3—H3···N1^ii	0.95	2.48	3.208 (2)	134

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

(XXII) N-(2-chloro-4-fluorophenyl)pyrazinecarboxamide

Crystal data

C11H7ClFN3O	F(000) = 512
Mr = 251.65	Dx = 1.583 Mg m^−3
Monoclinic, Cc	Synchrotron radiation, λ = 0.6709 Å
Hall symbol: C -2yc	Cell parameters from 2980 reflections
a = 18.733 (4) Å	θ = 3.1–28.6°
b = 3.8502 (8) Å	µ = 0.36 mm^−1
c = 14.839 (3) Å	T = 120 K
β = 99.472 (3)°	Block, colourless
V = 1055.7 (4) Å^3	0.07 × 0.05 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEXII CCD diffractometer	2980 independent reflections
Radiation source: Daresbury SRS station 9.8, Cernik et al., 1997, Clegg, 2003	2888 reflections with I > 2σ(I)
Silicon 111 monochromator	Rint = 0.017
fine–slice ω scans	θmax = 28.6°, θmin = 3.1°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −26→25
Tmin = 0.975, Tmax = 0.989	k = −5→5
5237 measured reflections	l = −21→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2980 reflections	Δρmax = 0.51 e Å^−3
154 parameters	Δρmin = −0.30 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1364 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (4)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.58972 (8)	0.7356 (4)	0.13943 (10)	0.0244 (3)
C2	0.61812 (9)	0.8121 (4)	0.22615 (11)	0.0215 (3)
C3	0.68266 (8)	0.9941 (4)	0.24885 (11)	0.0242 (3)
N4	0.72057 (8)	1.1033 (4)	0.18514 (11)	0.0274 (3)
C5	0.69254 (9)	1.0259 (5)	0.09870 (12)	0.0279 (3)
C6	0.62763 (10)	0.8435 (4)	0.07578 (12)	0.0273 (3)
C7	0.57815 (8)	0.6966 (4)	0.30107 (10)	0.0214 (3)
O7	0.60173 (7)	0.7537 (4)	0.38139 (9)	0.0301 (3)
N17	0.51543 (7)	0.5244 (3)	0.26860 (8)	0.0207 (2)
C11	0.46288 (8)	0.3994 (4)	0.31769 (9)	0.0188 (3)
C12	0.40303 (8)	0.2219 (4)	0.26962 (10)	0.0195 (3)
Cl12	0.39651 (2)	0.15255 (9)	0.15311 (2)	0.02557 (10)
C13	0.34726 (9)	0.0970 (4)	0.31201 (11)	0.0221 (3)
C14	0.35301 (9)	0.1533 (4)	0.40452 (11)	0.0241 (3)
F14	0.29899 (6)	0.0320 (3)	0.44732 (8)	0.0336 (2)
C15	0.41079 (9)	0.3241 (4)	0.45536 (11)	0.0251 (3)
C16	0.46593 (9)	0.4476 (4)	0.41160 (10)	0.0220 (3)
H3	0.7004	1.0424	0.3113	0.029*
H5	0.7176	1.0975	0.0512	0.033*
H6	0.6099	0.7946	0.0133	0.033*
H17	0.5063	0.4974	0.2089	0.025*
H13	0.3070	−0.0219	0.2786	0.027*
H15	0.4129	0.3568	0.5192	0.030*
H16	0.5060	0.5657	0.4458	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0255 (6)	0.0302 (6)	0.0176 (6)	−0.0034 (5)	0.0037 (5)	0.0001 (5)
C2	0.0230 (6)	0.0233 (6)	0.0179 (7)	0.0000 (5)	0.0029 (5)	0.0005 (5)
C3	0.0227 (6)	0.0286 (7)	0.0206 (7)	−0.0013 (5)	0.0021 (5)	−0.0016 (5)
N4	0.0249 (6)	0.0312 (7)	0.0263 (7)	−0.0029 (5)	0.0051 (5)	0.0008 (5)
C5	0.0280 (8)	0.0318 (8)	0.0249 (8)	−0.0033 (6)	0.0076 (6)	0.0036 (6)
C6	0.0299 (7)	0.0341 (8)	0.0177 (7)	−0.0046 (6)	0.0040 (6)	0.0022 (5)
C7	0.0219 (6)	0.0245 (6)	0.0169 (7)	0.0002 (5)	0.0010 (5)	0.0000 (5)
O7	0.0303 (6)	0.0420 (6)	0.0169 (5)	−0.0068 (5)	0.0009 (4)	−0.0038 (5)
N17	0.0235 (6)	0.0260 (6)	0.0125 (5)	−0.0027 (4)	0.0031 (4)	−0.0004 (4)
C11	0.0221 (6)	0.0216 (6)	0.0129 (6)	0.0020 (5)	0.0029 (5)	0.0002 (5)
C12	0.0241 (6)	0.0228 (6)	0.0113 (6)	0.0013 (5)	0.0022 (5)	0.0007 (5)
Cl12	0.03339 (18)	0.03120 (17)	0.01166 (14)	−0.00544 (15)	0.00246 (11)	−0.00179 (13)
C13	0.0233 (6)	0.0244 (6)	0.0189 (7)	0.0004 (5)	0.0038 (5)	0.0018 (5)
C14	0.0270 (7)	0.0267 (7)	0.0205 (7)	0.0015 (5)	0.0096 (6)	0.0036 (5)
F14	0.0357 (5)	0.0425 (6)	0.0263 (5)	−0.0045 (4)	0.0160 (4)	0.0023 (4)
C15	0.0342 (8)	0.0268 (7)	0.0152 (6)	0.0025 (5)	0.0070 (6)	−0.0005 (5)
C16	0.0275 (7)	0.0242 (6)	0.0140 (6)	0.0016 (5)	0.0024 (5)	0.0005 (5)

Geometric parameters (Å, º)

N1—C6	1.338 (2)	N17—H17	0.88
N1—C2	1.342 (2)	C11—C16	1.398 (2)
C2—C3	1.390 (2)	C11—C12	1.4033 (19)
C2—C7	1.506 (2)	C12—C13	1.391 (2)
C3—N4	1.340 (2)	C12—Cl12	1.7337 (15)
C3—H3	0.95	C13—C14	1.376 (2)
N4—C5	1.337 (2)	C13—H13	0.95
C5—C6	1.397 (2)	C14—F14	1.3627 (18)
C5—H5	0.95	C14—C15	1.380 (2)
C6—H6	0.95	C15—C16	1.391 (2)
C7—O7	1.2209 (19)	C15—H15	0.95
C7—N17	1.3659 (19)	C16—H16	0.95
N17—C11	1.4028 (18)
C6—N1—C2	115.87 (14)	C11—N17—H17	116.4
N1—C2—C3	122.33 (15)	C16—C11—N17	123.72 (13)
N1—C2—C7	118.44 (13)	C16—C11—C12	118.01 (13)
C3—C2—C7	119.23 (14)	N17—C11—C12	118.25 (12)
N4—C3—C2	121.87 (15)	C13—C12—C11	122.36 (13)
N4—C3—H3	119.1	C13—C12—Cl12	117.56 (11)
C2—C3—H3	119.1	C11—C12—Cl12	120.08 (11)
C5—N4—C3	115.89 (14)	C14—C13—C12	117.09 (15)
N4—C5—C6	122.30 (15)	C14—C13—H13	121.5
N4—C5—H5	118.8	C12—C13—H13	121.5
C6—C5—H5	118.8	F14—C14—C13	117.95 (15)
N1—C6—C5	121.73 (16)	F14—C14—C15	118.97 (15)
N1—C6—H6	119.1	C13—C14—C15	123.10 (15)
C5—C6—H6	119.1	C14—C15—C16	118.91 (15)
O7—C7—N17	125.72 (14)	C14—C15—H15	120.6
O7—C7—C2	121.57 (14)	C16—C15—H15	120.6
N17—C7—C2	112.71 (13)	C15—C16—C11	120.55 (14)
C7—N17—C11	128.30 (12)	C15—C16—H16	119.7
C7—N17—H17	115.2	C11—C16—H16	119.7
C6—N1—C2—C3	0.4 (2)	C7—N17—C11—C12	−178.63 (14)
C6—N1—C2—C7	−179.77 (14)	C16—C11—C12—C13	0.5 (2)
N1—C2—C3—N4	−0.2 (2)	N17—C11—C12—C13	−178.21 (14)
C7—C2—C3—N4	179.98 (14)	C16—C11—C12—Cl12	−179.69 (11)
C2—C3—N4—C5	−0.1 (2)	N17—C11—C12—Cl12	1.58 (18)
C3—N4—C5—C6	0.2 (3)	C11—C12—C13—C14	−0.2 (2)
C2—N1—C6—C5	−0.3 (2)	Cl12—C12—C13—C14	179.95 (12)
N4—C5—C6—N1	0.0 (3)	C12—C13—C14—F14	−179.82 (13)
N1—C2—C7—O7	178.87 (16)	C12—C13—C14—C15	−0.2 (2)
C3—C2—C7—O7	−1.3 (2)	F14—C14—C15—C16	179.96 (14)
N1—C2—C7—N17	−0.47 (19)	C13—C14—C15—C16	0.3 (2)
C3—C2—C7—N17	179.36 (14)	C14—C15—C16—C11	0.0 (2)
O7—C7—N17—C11	4.8 (3)	N17—C11—C16—C15	178.28 (13)
C2—C7—N17—C11	−175.85 (13)	C12—C11—C16—C15	−0.4 (2)
C7—N17—C11—C16	2.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.21	2.674 (2)	113
C13—H13···N4^i	0.95	2.43	3.364 (2)	170

Symmetry code: (i) x−1/2, y−3/2, z.

(XXIII) N-(4-chloro-2-fluorophenyl)pyrazinecarboxamide

Crystal data

C11H7ClFN3O	F(000) = 512
Mr = 251.65	Dx = 1.590 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2414 reflections
a = 6.8885 (2) Å	θ = 3.4–27.6°
b = 10.5369 (5) Å	µ = 0.36 mm^−1
c = 14.6683 (7) Å	T = 120 K
β = 99.008 (3)°	Needle, colourless
V = 1051.54 (8) Å^3	0.48 × 0.08 × 0.06 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2414 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.4°
ϕ & ω scans	h = −8→8
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −13→13
Tmin = 0.845, Tmax = 0.979	l = −19→19
14068 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 0.780P] where P = (Fo^2 + 2Fc^2)/3
2414 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1577 (3)	0.33660 (18)	0.33583 (12)	0.0259 (4)
C2	0.1690 (3)	0.2941 (2)	0.42208 (15)	0.0234 (5)
C3	0.1414 (3)	0.1672 (2)	0.44199 (16)	0.0277 (5)
N4	0.1037 (3)	0.07971 (19)	0.37480 (14)	0.0320 (5)
C5	0.0927 (3)	0.1227 (2)	0.28893 (17)	0.0306 (5)
C6	0.1194 (3)	0.2500 (2)	0.26898 (16)	0.0305 (5)
C7	0.2147 (3)	0.3886 (2)	0.49933 (14)	0.0236 (5)
O7	0.2190 (3)	0.35856 (16)	0.57997 (11)	0.0356 (4)
N17	0.2490 (3)	0.50689 (16)	0.46880 (12)	0.0233 (4)
C11	0.2903 (3)	0.6177 (2)	0.52125 (15)	0.0219 (4)
C12	0.2996 (3)	0.7310 (2)	0.47305 (14)	0.0238 (5)
F12	0.2682 (2)	0.72518 (13)	0.37956 (8)	0.0322 (3)
C13	0.3350 (3)	0.8472 (2)	0.51551 (15)	0.0263 (5)
C14	0.3653 (3)	0.8498 (2)	0.61107 (16)	0.0254 (5)
Cl14	0.40321 (9)	0.99463 (5)	0.66766 (4)	0.0335 (2)
C15	0.3618 (3)	0.7396 (2)	0.66226 (15)	0.0248 (5)
C16	0.3249 (3)	0.6233 (2)	0.61750 (14)	0.0243 (5)
H3	0.1494	0.1415	0.5046	0.033*
H5	0.0654	0.0643	0.2393	0.037*
H6	0.1102	0.2758	0.2064	0.037*
H17	0.2354	0.5103	0.4074	0.028*
H13	0.3384	0.9228	0.4805	0.032*
H15	0.3845	0.7433	0.7278	0.030*
H16	0.3234	0.5477	0.6526	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0250 (10)	0.0298 (10)	0.0234 (9)	−0.0008 (8)	0.0051 (7)	−0.0041 (7)
C2	0.0197 (10)	0.0257 (11)	0.0251 (11)	0.0036 (8)	0.0046 (8)	−0.0023 (8)
C3	0.0294 (12)	0.0241 (11)	0.0287 (12)	0.0051 (9)	0.0019 (9)	−0.0012 (9)
N4	0.0337 (11)	0.0264 (10)	0.0350 (11)	0.0043 (8)	0.0028 (8)	−0.0058 (8)
C5	0.0257 (12)	0.0351 (13)	0.0302 (12)	0.0017 (10)	0.0019 (9)	−0.0103 (10)
C6	0.0305 (13)	0.0356 (13)	0.0255 (12)	−0.0017 (10)	0.0046 (9)	−0.0057 (9)
C7	0.0253 (11)	0.0227 (11)	0.0231 (11)	0.0037 (9)	0.0045 (8)	−0.0020 (8)
O7	0.0574 (12)	0.0282 (9)	0.0214 (8)	−0.0003 (8)	0.0071 (7)	−0.0001 (6)
N17	0.0280 (10)	0.0229 (9)	0.0189 (8)	0.0017 (7)	0.0036 (7)	−0.0010 (7)
C11	0.0194 (10)	0.0221 (10)	0.0244 (11)	0.0033 (8)	0.0043 (8)	−0.0008 (8)
C12	0.0242 (11)	0.0267 (11)	0.0207 (10)	0.0043 (9)	0.0039 (8)	0.0014 (8)
F12	0.0463 (8)	0.0301 (7)	0.0200 (7)	−0.0011 (6)	0.0044 (6)	0.0020 (5)
C13	0.0263 (12)	0.0223 (11)	0.0303 (12)	0.0018 (8)	0.0048 (9)	0.0020 (8)
C14	0.0217 (11)	0.0238 (11)	0.0308 (12)	0.0016 (8)	0.0047 (8)	−0.0052 (8)
Cl14	0.0376 (4)	0.0270 (3)	0.0351 (3)	0.0008 (2)	0.0034 (2)	−0.0084 (2)
C15	0.0242 (11)	0.0293 (11)	0.0210 (11)	0.0026 (9)	0.0041 (8)	−0.0024 (8)
C16	0.0234 (11)	0.0276 (11)	0.0222 (11)	0.0040 (9)	0.0049 (8)	0.0021 (8)

Geometric parameters (Å, º)

N1—C2	1.333 (3)	N17—H17	0.89
N1—C6	1.335 (3)	C11—C12	1.394 (3)
C2—C3	1.388 (3)	C11—C16	1.396 (3)
C2—C7	1.504 (3)	C12—F12	1.356 (2)
C3—N4	1.345 (3)	C12—C13	1.379 (3)
C3—H3	0.95	C13—C14	1.385 (3)
N4—C5	1.330 (3)	C13—H13	0.95
C5—C6	1.391 (3)	C14—C15	1.385 (3)
C5—H5	0.95	C14—Cl14	1.737 (2)
C6—H6	0.95	C15—C16	1.394 (3)
C7—O7	1.220 (3)	C15—H15	0.95
C7—N17	1.358 (3)	C16—H16	0.95
N17—C11	1.402 (3)
C2—N1—C6	116.3 (2)	C11—N17—H17	120.1
N1—C2—C3	122.3 (2)	C12—C11—C16	117.5 (2)
N1—C2—C7	117.83 (19)	C12—C11—N17	117.12 (18)
C3—C2—C7	119.9 (2)	C16—C11—N17	125.35 (19)
N4—C3—C2	121.6 (2)	F12—C12—C13	119.07 (19)
N4—C3—H3	119.2	F12—C12—C11	117.51 (19)
C2—C3—H3	119.2	C13—C12—C11	123.4 (2)
C5—N4—C3	115.9 (2)	C12—C13—C14	117.6 (2)
N4—C5—C6	122.6 (2)	C12—C13—H13	121.2
N4—C5—H5	118.7	C14—C13—H13	121.2
C6—C5—H5	118.7	C15—C14—C13	121.3 (2)
N1—C6—C5	121.5 (2)	C15—C14—Cl14	119.43 (17)
N1—C6—H6	119.3	C13—C14—Cl14	119.23 (17)
C5—C6—H6	119.3	C14—C15—C16	119.9 (2)
O7—C7—N17	125.4 (2)	C14—C15—H15	120.0
O7—C7—C2	121.9 (2)	C16—C15—H15	120.0
N17—C7—C2	112.70 (18)	C15—C16—C11	120.2 (2)
C7—N17—C11	127.87 (18)	C15—C16—H16	119.9
C7—N17—H17	111.9	C11—C16—H16	119.9
C6—N1—C2—C3	−0.5 (3)	C7—N17—C11—C16	7.4 (3)
C6—N1—C2—C7	179.18 (19)	C16—C11—C12—F12	179.25 (18)
N1—C2—C3—N4	0.8 (3)	N17—C11—C12—F12	−0.1 (3)
C7—C2—C3—N4	−178.9 (2)	C16—C11—C12—C13	−2.0 (3)
C2—C3—N4—C5	−0.7 (3)	N17—C11—C12—C13	178.7 (2)
C3—N4—C5—C6	0.4 (3)	F12—C12—C13—C14	179.65 (19)
C2—N1—C6—C5	0.1 (3)	C11—C12—C13—C14	1.0 (3)
N4—C5—C6—N1	−0.1 (4)	C12—C13—C14—C15	0.5 (3)
N1—C2—C7—O7	176.6 (2)	C12—C13—C14—Cl14	−178.12 (17)
C3—C2—C7—O7	−3.7 (3)	C13—C14—C15—C16	−0.7 (3)
N1—C2—C7—N17	−3.3 (3)	Cl14—C14—C15—C16	177.86 (16)
C3—C2—C7—N17	176.31 (19)	C14—C15—C16—C11	−0.4 (3)
O7—C7—N17—C11	−1.8 (4)	C12—C11—C16—C15	1.7 (3)
C2—C7—N17—C11	178.13 (18)	N17—C11—C16—C15	−179.0 (2)
C7—N17—C11—C12	−173.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.89	2.14	2.652 (3)	116

(XXIV) N-(2-methyl-5-nitrophenyl)pyrazinecarboxamide

Crystal data

C12H10N4O3	F(000) = 536
Mr = 258.24	Dx = 1.457 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2723 reflections
a = 10.4767 (5) Å	θ = 3.3–27.5°
b = 14.5930 (6) Å	µ = 0.11 mm^−1
c = 7.7136 (3) Å	T = 120 K
β = 93.433 (3)°	Plate, colourless
V = 1177.19 (9) Å^3	0.34 × 0.04 × 0.02 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2711 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1936 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ & ω scans	h = −13→13
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	k = −18→18
Tmin = 0.977, Tmax = 0.998	l = −10→9
26700 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.635P] where P = (Fo^2 + 2Fc^2)/3
2711 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.44260 (18)	0.25515 (13)	0.6088 (2)	0.0360 (5)
C2	0.3756 (2)	0.18393 (14)	0.5420 (3)	0.0308 (5)
C3	0.4112 (2)	0.09426 (17)	0.5781 (3)	0.0424 (6)
N4	0.5132 (2)	0.07421 (15)	0.6834 (3)	0.0516 (6)
C5	0.5794 (2)	0.14576 (19)	0.7478 (3)	0.0481 (7)
C6	0.5447 (2)	0.23544 (18)	0.7107 (3)	0.0412 (6)
C7	0.2592 (2)	0.20506 (14)	0.4266 (3)	0.0300 (5)
O7	0.19677 (15)	0.14521 (10)	0.3492 (2)	0.0370 (4)
N17	0.23298 (16)	0.29586 (11)	0.4201 (2)	0.0300 (4)
C11	0.1330 (2)	0.34329 (14)	0.3318 (3)	0.0294 (5)
C12	0.1307 (2)	0.43932 (14)	0.3521 (3)	0.0328 (5)
C121	0.2343 (2)	0.48820 (15)	0.4598 (3)	0.0401 (6)
C13	0.0320 (2)	0.48825 (15)	0.2678 (3)	0.0365 (5)
C14	−0.0629 (2)	0.44588 (15)	0.1633 (3)	0.0356 (5)
C15	−0.0564 (2)	0.35240 (15)	0.1465 (3)	0.0317 (5)
N15	−0.15470 (17)	0.30635 (14)	0.0344 (2)	0.0365 (5)
O151	−0.22843 (17)	0.35439 (12)	−0.0560 (2)	0.0506 (5)
O152	−0.15942 (16)	0.22235 (12)	0.0363 (2)	0.0466 (5)
C16	0.03822 (19)	0.29911 (15)	0.2284 (3)	0.0298 (5)
H3	0.3618	0.0457	0.5266	0.051*
H5	0.6534	0.1347	0.8222	0.058*
H6	0.5955	0.2839	0.7596	0.049*
H17	0.2891	0.3264	0.4870	0.036*
H12A	0.2171	0.5542	0.4584	0.060*
H12B	0.3172	0.4765	0.4115	0.060*
H12C	0.2360	0.4657	0.5796	0.060*
H13	0.0293	0.5529	0.2822	0.044*
H14	−0.1297	0.4802	0.1056	0.043*
H16	0.0386	0.2344	0.2147	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0314 (10)	0.0425 (11)	0.0336 (10)	−0.0023 (8)	−0.0019 (8)	−0.0017 (8)
C2	0.0318 (11)	0.0332 (12)	0.0275 (10)	0.0034 (9)	0.0022 (9)	−0.0024 (9)
C3	0.0434 (14)	0.0410 (14)	0.0418 (13)	0.0113 (11)	−0.0070 (11)	−0.0038 (10)
N4	0.0536 (14)	0.0528 (14)	0.0467 (12)	0.0189 (11)	−0.0098 (10)	−0.0007 (10)
C5	0.0383 (13)	0.0684 (18)	0.0363 (13)	0.0141 (13)	−0.0072 (10)	−0.0016 (12)
C6	0.0310 (12)	0.0588 (16)	0.0330 (12)	−0.0010 (11)	−0.0039 (10)	−0.0040 (11)
C7	0.0308 (11)	0.0271 (11)	0.0319 (11)	−0.0002 (9)	0.0007 (9)	−0.0020 (9)
O7	0.0403 (9)	0.0266 (8)	0.0430 (9)	−0.0012 (7)	−0.0070 (7)	−0.0053 (6)
N17	0.0296 (9)	0.0248 (9)	0.0345 (9)	−0.0015 (7)	−0.0054 (7)	−0.0017 (7)
C11	0.0290 (11)	0.0292 (11)	0.0298 (11)	−0.0012 (8)	−0.0005 (9)	−0.0009 (8)
C12	0.0389 (12)	0.0262 (11)	0.0326 (11)	−0.0007 (9)	−0.0031 (9)	−0.0005 (8)
C121	0.0494 (14)	0.0286 (12)	0.0408 (13)	−0.0024 (10)	−0.0104 (10)	−0.0018 (9)
C13	0.0444 (14)	0.0269 (11)	0.0375 (12)	0.0039 (9)	−0.0029 (10)	0.0006 (9)
C14	0.0354 (12)	0.0342 (12)	0.0367 (12)	0.0052 (9)	−0.0026 (9)	0.0031 (9)
C15	0.0282 (11)	0.0371 (12)	0.0295 (11)	−0.0021 (9)	−0.0004 (9)	−0.0012 (9)
N15	0.0289 (10)	0.0427 (12)	0.0376 (10)	−0.0023 (8)	−0.0008 (8)	−0.0024 (9)
O151	0.0409 (10)	0.0560 (11)	0.0525 (11)	−0.0004 (8)	−0.0169 (8)	0.0043 (8)
O152	0.0402 (10)	0.0391 (10)	0.0593 (11)	−0.0043 (7)	−0.0068 (8)	−0.0083 (8)
C16	0.0298 (11)	0.0265 (11)	0.0330 (11)	−0.0015 (8)	0.0007 (9)	−0.0019 (8)

Geometric parameters (Å, º)

N1—C6	1.321 (3)	C11—C12	1.410 (3)
N1—C2	1.340 (3)	C12—C13	1.386 (3)
C2—C3	1.384 (3)	C12—C121	1.507 (3)
C2—C7	1.498 (3)	C121—H12A	0.98
C3—N4	1.335 (3)	C121—H12B	0.98
C3—H3	0.95	C121—H12C	0.98
N4—C5	1.333 (3)	C13—C14	1.388 (3)
C5—C6	1.384 (4)	C13—H13	0.95
C5—H5	0.95	C14—C15	1.372 (3)
C6—H6	0.95	C14—H14	0.95
C7—O7	1.225 (2)	C15—C16	1.383 (3)
C7—N17	1.354 (3)	C15—N15	1.467 (3)
N17—C11	1.398 (3)	N15—O152	1.227 (2)
N17—H17	0.88	N15—O151	1.229 (2)
C11—C16	1.394 (3)	C16—H16	0.95
C6—N1—C2	116.5 (2)	C13—C12—C121	120.49 (19)
N1—C2—C3	121.9 (2)	C11—C12—C121	121.00 (19)
N1—C2—C7	117.24 (19)	C12—C121—H12A	109.5
C3—C2—C7	120.90 (19)	C12—C121—H12B	109.5
N4—C3—C2	121.7 (2)	H12A—C121—H12B	109.5
N4—C3—H3	119.2	C12—C121—H12C	109.5
C2—C3—H3	119.2	H12A—C121—H12C	109.5
C5—N4—C3	115.8 (2)	H12B—C121—H12C	109.5
N4—C5—C6	122.6 (2)	C12—C13—C14	122.1 (2)
N4—C5—H5	118.7	C12—C13—H13	118.9
C6—C5—H5	118.7	C14—C13—H13	118.9
N1—C6—C5	121.5 (2)	C15—C14—C13	117.4 (2)
N1—C6—H6	119.3	C15—C14—H14	121.3
C5—C6—H6	119.3	C13—C14—H14	121.3
O7—C7—N17	125.34 (19)	C14—C15—C16	123.7 (2)
O7—C7—C2	122.34 (19)	C14—C15—N15	118.27 (19)
N17—C7—C2	112.32 (17)	C16—C15—N15	118.07 (19)
C7—N17—C11	130.34 (17)	O152—N15—O151	123.52 (19)
C7—N17—H17	110.3	O152—N15—C15	118.55 (18)
C11—N17—H17	119.3	O151—N15—C15	117.93 (19)
C16—C11—N17	122.47 (18)	C15—C16—C11	117.9 (2)
C16—C11—C12	120.45 (19)	C15—C16—H16	121.0
N17—C11—C12	117.08 (18)	C11—C16—H16	121.0
C13—C12—C11	118.5 (2)
C6—N1—C2—C3	0.1 (3)	N17—C11—C12—C13	−179.29 (19)
C6—N1—C2—C7	179.79 (19)	C16—C11—C12—C121	−178.5 (2)
N1—C2—C3—N4	1.0 (4)	N17—C11—C12—C121	1.9 (3)
C7—C2—C3—N4	−178.6 (2)	C11—C12—C13—C14	−0.8 (3)
C2—C3—N4—C5	−1.4 (4)	C121—C12—C13—C14	178.0 (2)
C3—N4—C5—C6	0.8 (4)	C12—C13—C14—C15	0.4 (3)
C2—N1—C6—C5	−0.8 (3)	C13—C14—C15—C16	0.5 (3)
N4—C5—C6—N1	0.3 (4)	C13—C14—C15—N15	−179.11 (19)
N1—C2—C7—O7	174.6 (2)	C14—C15—N15—O152	−170.6 (2)
C3—C2—C7—O7	−5.8 (3)	C16—C15—N15—O152	9.7 (3)
N1—C2—C7—N17	−5.6 (3)	C14—C15—N15—O151	9.1 (3)
C3—C2—C7—N17	174.0 (2)	C16—C15—N15—O151	−170.54 (19)
O7—C7—N17—C11	1.2 (4)	C14—C15—C16—C11	−0.9 (3)
C2—C7—N17—C11	−178.6 (2)	N15—C15—C16—C11	178.67 (18)
C7—N17—C11—C16	−0.3 (3)	N17—C11—C16—C15	−179.89 (19)
C7—N17—C11—C12	179.4 (2)	C12—C11—C16—C15	0.5 (3)
C16—C11—C12—C13	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N1	0.88	2.09	2.630 (2)	119
C6—H6···O151^i	0.95	2.48	3.373 (3)	156
C14—H14···O7^ii	0.95	2.54	3.228 (3)	130

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