N-(2-Hydroxy­ethyl)pyrazine-2-carboxamide

The title compound, C₇H₉N₃O₂, crystallizes with two independent mol­ecules in the asymmetric unit. The amide group lies almost in the pyrazine plane. Each mol­ecule is linked to three other mol­ecules by means of hydrogen bonds, giving rise to a ladder-like two-dimensional network. Adjacent two-dimensional networks are linked by hydrogen bonds to form a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.134
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.106
            Value of mu given      =     0.110

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N-(2-Hydroxyethyl)pyrazine-2-carboxamide

Crystal data

C7H9N3O2	Z = 4
Mr = 167.17	F(000) = 352
Triclinic, P1	Dx = 1.399 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3054 (12) Å	Cell parameters from 1336 reflections
b = 7.8287 (19) Å	θ = 2.7–25.6°
c = 19.880 (5) Å	µ = 0.11 mm^−1
α = 86.953 (4)°	T = 294 K
β = 87.262 (4)°	Block, colourless
γ = 74.451 (4)°	0.28 × 0.20 × 0.16 mm
V = 793.9 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3197 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.962, Tmax = 0.983	k = −9→8
4504 measured reflections	l = −24→15

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.0883P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3197 reflections	Δρmax = 0.24 e Å^−3
228 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (5)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.2083 (4)	0.3372 (2)	0.24175 (9)	0.0409 (5)
N2	−0.2735 (4)	0.5184 (3)	0.18822 (11)	0.0518 (6)
N3	0.3110 (4)	0.3859 (3)	0.36994 (10)	0.0396 (5)
H3	0.405 (5)	0.316 (3)	0.3424 (12)	0.048 (7)*
N4	0.2316 (4)	0.8528 (3)	0.26789 (9)	0.0425 (5)
N5	−0.2027 (4)	1.0893 (3)	0.32754 (10)	0.0524 (6)
N6	0.2069 (4)	0.7568 (3)	0.13834 (10)	0.0436 (5)
H6	0.326 (5)	0.714 (4)	0.1646 (14)	0.066 (9)*
O1	−0.0790 (3)	0.5936 (2)	0.38138 (8)	0.0526 (5)
O2	0.1559 (4)	0.2186 (3)	0.49932 (9)	0.0631 (6)
H2	0.1057	0.2740	0.5335	0.095*
O3	−0.1852 (3)	0.9577 (2)	0.12904 (9)	0.0642 (6)
O4	0.4084 (5)	0.7642 (3)	−0.04072 (9)	0.0779 (6)
H4	0.3353	0.8474	−0.0658	0.117*
C1	0.0246 (4)	0.4501 (3)	0.27757 (10)	0.0330 (5)
C2	−0.2126 (4)	0.5384 (3)	0.25103 (12)	0.0448 (6)
H2A	−0.3352	0.6151	0.2781	0.054*
C3	−0.0898 (5)	0.4069 (3)	0.15268 (12)	0.0517 (7)
H3A	−0.1220	0.3889	0.1084	0.062*
C4	0.1471 (5)	0.3168 (3)	0.17885 (12)	0.0484 (6)
H4A	0.2684	0.2391	0.1518	0.058*
C5	0.0818 (4)	0.4830 (3)	0.34838 (11)	0.0365 (5)
C6	0.4113 (5)	0.3926 (3)	0.43607 (11)	0.0450 (6)
H6A	0.3057	0.4971	0.4580	0.054*
H6B	0.5891	0.4036	0.4310	0.054*
C7	0.4095 (5)	0.2305 (3)	0.48004 (12)	0.0495 (6)
H7A	0.4999	0.1257	0.4560	0.059*
H7B	0.5054	0.2321	0.5202	0.059*
C8	0.0132 (4)	0.9250 (3)	0.23437 (11)	0.0359 (5)
C9	−0.1990 (4)	1.0409 (3)	0.26423 (12)	0.0471 (6)
H9	−0.3468	1.0877	0.2390	0.057*
C10	0.0139 (5)	1.0182 (3)	0.36063 (12)	0.0476 (6)
H10	0.0220	1.0479	0.4050	0.057*
C11	0.2273 (5)	0.9018 (3)	0.33143 (12)	0.0472 (6)
H11	0.3746	0.8552	0.3569	0.057*
C12	0.0042 (4)	0.8809 (3)	0.16215 (11)	0.0414 (6)
C13	0.2332 (5)	0.7071 (3)	0.06827 (11)	0.0468 (6)
H13A	0.0609	0.7226	0.0506	0.056*
H13B	0.3277	0.5829	0.0657	0.056*
C14	0.3759 (6)	0.8178 (4)	0.02653 (12)	0.0629 (8)
H14A	0.2781	0.9416	0.0276	0.075*
H14B	0.5459	0.8057	0.0450	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0415 (11)	0.0459 (12)	0.0333 (11)	−0.0083 (9)	0.0016 (8)	−0.0046 (9)
N2	0.0505 (12)	0.0576 (14)	0.0463 (13)	−0.0114 (11)	−0.0117 (10)	0.0016 (10)
N3	0.0421 (11)	0.0451 (12)	0.0287 (11)	−0.0053 (10)	−0.0018 (9)	−0.0077 (9)
N4	0.0410 (11)	0.0494 (12)	0.0331 (11)	−0.0042 (9)	−0.0032 (8)	−0.0031 (9)
N5	0.0483 (12)	0.0565 (14)	0.0482 (13)	−0.0059 (10)	0.0048 (10)	−0.0122 (10)
N6	0.0425 (12)	0.0554 (13)	0.0283 (11)	−0.0041 (10)	−0.0040 (9)	−0.0034 (9)
O1	0.0515 (10)	0.0553 (11)	0.0443 (10)	−0.0007 (9)	0.0033 (8)	−0.0158 (8)
O2	0.0794 (13)	0.0709 (14)	0.0463 (12)	−0.0335 (11)	0.0162 (9)	−0.0159 (9)
O3	0.0579 (11)	0.0721 (13)	0.0514 (12)	0.0064 (10)	−0.0265 (9)	−0.0027 (9)
O4	0.1160 (18)	0.0773 (14)	0.0344 (11)	−0.0154 (13)	0.0012 (11)	−0.0037 (9)
C1	0.0316 (11)	0.0332 (12)	0.0332 (12)	−0.0072 (9)	0.0020 (9)	−0.0017 (9)
C2	0.0400 (13)	0.0480 (15)	0.0424 (14)	−0.0048 (11)	−0.0016 (11)	−0.0019 (11)
C3	0.0636 (17)	0.0592 (17)	0.0367 (14)	−0.0228 (14)	−0.0106 (13)	−0.0007 (12)
C4	0.0520 (15)	0.0557 (16)	0.0355 (14)	−0.0105 (12)	0.0053 (11)	−0.0095 (11)
C5	0.0399 (13)	0.0363 (13)	0.0329 (13)	−0.0096 (11)	0.0031 (10)	−0.0039 (10)
C6	0.0489 (14)	0.0483 (15)	0.0389 (14)	−0.0132 (11)	−0.0077 (11)	−0.0054 (11)
C7	0.0578 (15)	0.0505 (16)	0.0365 (14)	−0.0078 (12)	−0.0004 (11)	−0.0034 (11)
C8	0.0339 (12)	0.0355 (12)	0.0361 (13)	−0.0057 (10)	−0.0029 (10)	0.0009 (10)
C9	0.0399 (13)	0.0486 (15)	0.0490 (16)	−0.0043 (12)	−0.0037 (11)	−0.0032 (12)
C10	0.0557 (15)	0.0483 (15)	0.0406 (14)	−0.0165 (13)	0.0044 (12)	−0.0083 (11)
C11	0.0478 (14)	0.0578 (16)	0.0340 (14)	−0.0099 (12)	−0.0077 (11)	−0.0012 (11)
C12	0.0429 (13)	0.0441 (14)	0.0371 (13)	−0.0112 (11)	−0.0075 (11)	0.0012 (11)
C13	0.0512 (14)	0.0522 (15)	0.0358 (14)	−0.0103 (12)	−0.0035 (11)	−0.0072 (11)
C14	0.086 (2)	0.075 (2)	0.0327 (15)	−0.0306 (16)	−0.0017 (13)	−0.0025 (13)

Geometric parameters (Å, º)

N1—C1	1.333 (3)	C1—C5	1.504 (3)
N1—C4	1.335 (3)	C2—H2A	0.9300
N2—C3	1.324 (3)	C3—C4	1.377 (3)
N2—C2	1.332 (3)	C3—H3A	0.9300
N3—C5	1.327 (3)	C4—H4A	0.9300
N3—C6	1.450 (3)	C6—C7	1.504 (3)
N3—H3	0.84 (2)	C6—H6A	0.9700
N4—C11	1.337 (3)	C6—H6B	0.9700
N4—C8	1.337 (3)	C7—H7A	0.9700
N5—C10	1.325 (3)	C7—H7B	0.9700
N5—C9	1.331 (3)	C8—C9	1.374 (3)
N6—C12	1.328 (3)	C8—C12	1.500 (3)
N6—C13	1.456 (3)	C9—H9	0.9300
N6—H6	0.83 (3)	C10—C11	1.375 (3)
O1—C5	1.232 (2)	C10—H10	0.9300
O2—C7	1.408 (3)	C11—H11	0.9300
O2—H2	0.8200	C13—C14	1.492 (4)
O3—C12	1.226 (3)	C13—H13A	0.9700
O4—C14	1.411 (3)	C13—H13B	0.9700
O4—H4	0.8200	C14—H14A	0.9700
C1—C2	1.377 (3)	C14—H14B	0.9700
C1—N1—C4	115.57 (19)	O2—C7—C6	113.3 (2)
C3—N2—C2	115.3 (2)	O2—C7—H7A	108.9
C5—N3—C6	125.4 (2)	C6—C7—H7A	108.9
C5—N3—H3	116.5 (16)	O2—C7—H7B	108.9
C6—N3—H3	118.1 (16)	C6—C7—H7B	108.9
C11—N4—C8	115.4 (2)	H7A—C7—H7B	107.7
C10—N5—C9	115.5 (2)	N4—C8—C9	121.4 (2)
C12—N6—C13	122.7 (2)	N4—C8—C12	118.8 (2)
C12—N6—H6	116.7 (19)	C9—C8—C12	119.8 (2)
C13—N6—H6	120.4 (19)	N5—C9—C8	123.1 (2)
C7—O2—H2	109.5	N5—C9—H9	118.5
C14—O4—H4	109.5	C8—C9—H9	118.5
N1—C1—C2	121.7 (2)	N5—C10—C11	122.0 (2)
N1—C1—C5	118.59 (18)	N5—C10—H10	119.0
C2—C1—C5	119.7 (2)	C11—C10—H10	119.0
N2—C2—C1	122.7 (2)	N4—C11—C10	122.6 (2)
N2—C2—H2A	118.6	N4—C11—H11	118.7
C1—C2—H2A	118.6	C10—C11—H11	118.7
N2—C3—C4	122.5 (2)	O3—C12—N6	124.0 (2)
N2—C3—H3A	118.8	O3—C12—C8	119.6 (2)
C4—C3—H3A	118.8	N6—C12—C8	116.42 (19)
N1—C4—C3	122.2 (2)	N6—C13—C14	110.9 (2)
N1—C4—H4A	118.9	N6—C13—H13A	109.5
C3—C4—H4A	118.9	C14—C13—H13A	109.5
O1—C5—N3	125.3 (2)	N6—C13—H13B	109.5
O1—C5—C1	119.93 (19)	C14—C13—H13B	109.5
N3—C5—C1	114.78 (19)	H13A—C13—H13B	108.0
N3—C6—C7	112.40 (19)	O4—C14—C13	110.4 (2)
N3—C6—H6A	109.1	O4—C14—H14A	109.6
C7—C6—H6A	109.1	C13—C14—H14A	109.6
N3—C6—H6B	109.1	O4—C14—H14B	109.6
C7—C6—H6B	109.1	C13—C14—H14B	109.6
H6A—C6—H6B	107.9	H14A—C14—H14B	108.1
C4—N1—C1—C2	0.3 (3)	C11—N4—C8—C9	−0.2 (3)
C4—N1—C1—C5	−178.69 (19)	C11—N4—C8—C12	178.4 (2)
C3—N2—C2—C1	0.1 (3)	C10—N5—C9—C8	0.1 (4)
N1—C1—C2—N2	−0.5 (3)	N4—C8—C9—N5	0.1 (4)
C5—C1—C2—N2	178.5 (2)	C12—C8—C9—N5	−178.4 (2)
C2—N2—C3—C4	0.5 (4)	C9—N5—C10—C11	−0.2 (4)
C1—N1—C4—C3	0.3 (3)	C8—N4—C11—C10	0.0 (3)
N2—C3—C4—N1	−0.7 (4)	N5—C10—C11—N4	0.2 (4)
C6—N3—C5—O1	0.3 (4)	C13—N6—C12—O3	4.3 (4)
C6—N3—C5—C1	−179.90 (19)	C13—N6—C12—C8	−176.3 (2)
N1—C1—C5—O1	176.2 (2)	N4—C8—C12—O3	−173.6 (2)
C2—C1—C5—O1	−2.8 (3)	C9—C8—C12—O3	4.9 (3)
N1—C1—C5—N3	−3.6 (3)	N4—C8—C12—N6	7.0 (3)
C2—C1—C5—N3	177.3 (2)	C9—C8—C12—N6	−174.5 (2)
C5—N3—C6—C7	107.9 (3)	C12—N6—C13—C14	89.9 (3)
N3—C6—C7—O2	−68.4 (3)	N6—C13—C14—O4	177.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.82	1.94	2.763 (3)	176
O2—H2···O1^ii	0.82	2.01	2.813 (2)	166
N6—H6···N2^iii	0.83 (3)	2.31 (3)	3.062 (3)	151 (3)
N3—H3···N5^iv	0.84 (2)	2.36 (2)	3.090 (3)	145 (2)
N3—H3···N1	0.84 (2)	2.28 (2)	2.699 (3)	111.0 (19)

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