Methyl 5-methyl­pyrazine-2-carboxyl­ate

In the structure of methyl 5-methyl-2-pyrazine­carboxyl­ate, C₇H₈N₂O₂, the non-H atoms of the mol­ecule are nearly planar, with a dihedral angle of 5.4 (1)° between the plane of the pyrazine ring and the plane defined by C—C(O)—O. In the crystal, molecules are linked via C—H...N and C—H...O hydrogen bonds, forming layers parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.083
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  N2      ..       2.72 Ang.

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.66 mm
PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and s.u.        0.20 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Methyl 5-methylpyrazine-2-carboxylate

Crystal data

C7H8N2O2	F(000) = 160
Mr = 152.15	Dx = 1.397 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 3.8872 (1) Å	Cell parameters from 7189 reflections
b = 6.8386 (3) Å	θ = 3.0–27.0°
c = 13.6279 (5) Å	µ = 0.11 mm^−1
β = 93.303 (2)°	T = 150 K
V = 361.67 (2) Å^3	Block, clear colourless
Z = 2	0.66 × 0.65 × 0.56 mm

Data collection

Bruker APEXII CCD diffractometer	1556 independent reflections
Radiation source: sealed X-ray tube	1495 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 5.6 pixels mm^-1	θmax = 27.1°, θmin = 3.3°
φ and ω scans	h = −4→4
Absorption correction: numerical (SADABS; Bruker, 2012)	k = −8→8
Tmin = 0.925, Tmax = 0.976	l = −17→17
9931 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.0328P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.20 e Å^−3
1556 reflections	Δρmin = −0.17 e Å^−3
102 parameters	Absolute structure: Flack x determined using 659 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al, 2013)
1 restraint	Absolute structure parameter: 0.0 (2)
Primary atom site location: structure-invariant direct methods

Special details

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

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

	x	y	z	Uiso*/Ueq
O2	0.2766 (3)	0.74768 (19)	0.59049 (8)	0.0235 (3)
O1	0.5934 (4)	0.8742 (2)	0.71764 (10)	0.0338 (4)
N2	0.3528 (4)	0.4025 (2)	0.89293 (10)	0.0223 (3)
N1	0.1414 (4)	0.4246 (2)	0.69310 (10)	0.0211 (3)
C6	0.4125 (4)	0.7469 (3)	0.68198 (12)	0.0204 (4)
C4	0.3192 (4)	0.5692 (2)	0.73882 (12)	0.0182 (4)
C3	0.0722 (4)	0.2702 (3)	0.74819 (12)	0.0216 (4)
H3	−0.0525	0.1642	0.7184	0.026*
C2	0.1754 (4)	0.2572 (2)	0.84819 (12)	0.0194 (4)
C1	0.0880 (5)	0.0836 (3)	0.90848 (13)	0.0267 (4)
H1A	0.2996	0.0283	0.9397	0.040*
H1B	−0.0271	−0.0151	0.8660	0.040*
H1C	−0.0660	0.1238	0.9593	0.040*
C5	0.4222 (5)	0.5576 (3)	0.83769 (12)	0.0222 (4)
H5	0.5466	0.6639	0.8673	0.027*
C7	0.3671 (5)	0.9159 (3)	0.53238 (13)	0.0288 (4)
H7A	0.2383	0.9115	0.4685	0.043*
H7B	0.6148	0.9136	0.5225	0.043*
H7C	0.3093	1.0361	0.5669	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0286 (6)	0.0210 (6)	0.0206 (6)	−0.0053 (5)	−0.0005 (5)	0.0025 (5)
O1	0.0461 (9)	0.0243 (7)	0.0299 (7)	−0.0160 (7)	−0.0087 (6)	0.0030 (6)
N2	0.0241 (7)	0.0227 (7)	0.0197 (6)	−0.0011 (7)	−0.0008 (5)	−0.0011 (6)
N1	0.0240 (7)	0.0191 (7)	0.0200 (7)	−0.0038 (6)	−0.0006 (6)	−0.0012 (6)
C6	0.0219 (8)	0.0176 (8)	0.0215 (8)	0.0000 (7)	0.0004 (6)	0.0005 (7)
C4	0.0178 (8)	0.0162 (8)	0.0207 (8)	−0.0001 (6)	0.0012 (6)	−0.0011 (6)
C3	0.0242 (9)	0.0184 (8)	0.0220 (8)	−0.0050 (7)	−0.0003 (6)	−0.0018 (7)
C2	0.0165 (8)	0.0194 (8)	0.0225 (8)	0.0002 (7)	0.0018 (6)	0.0009 (7)
C1	0.0286 (10)	0.0258 (10)	0.0253 (9)	−0.0047 (8)	−0.0017 (7)	0.0079 (7)
C5	0.0249 (9)	0.0187 (8)	0.0225 (8)	−0.0023 (7)	−0.0018 (7)	−0.0029 (7)
C7	0.0343 (10)	0.0257 (9)	0.0264 (9)	−0.0040 (9)	0.0016 (7)	0.0085 (8)

Geometric parameters (Å, º)

O2—C6	1.3259 (19)	C3—C2	1.401 (2)
O2—C7	1.451 (2)	C2—C1	1.494 (2)
O1—C6	1.203 (2)	C1—H1A	0.9800
N2—C2	1.337 (2)	C1—H1B	0.9800
N2—C5	1.337 (2)	C1—H1C	0.9800
N1—C4	1.339 (2)	C5—H5	0.9500
N1—C3	1.332 (2)	C7—H7A	0.9800
C6—C4	1.497 (2)	C7—H7B	0.9800
C4—C5	1.386 (2)	C7—H7C	0.9800
C3—H3	0.9500
C6—O2—C7	114.85 (14)	C2—C1—H1A	109.5
C2—N2—C5	116.65 (14)	C2—C1—H1B	109.5
C3—N1—C4	116.01 (13)	C2—C1—H1C	109.5
O2—C6—C4	113.23 (14)	H1A—C1—H1B	109.5
O1—C6—O2	124.67 (16)	H1A—C1—H1C	109.5
O1—C6—C4	122.10 (15)	H1B—C1—H1C	109.5
N1—C4—C6	119.51 (14)	N2—C5—C4	122.43 (16)
N1—C4—C5	121.52 (15)	N2—C5—H5	118.8
C5—C4—C6	118.97 (14)	C4—C5—H5	118.8
N1—C3—H3	118.6	O2—C7—H7A	109.5
N1—C3—C2	122.86 (15)	O2—C7—H7B	109.5
C2—C3—H3	118.6	O2—C7—H7C	109.5
N2—C2—C3	120.52 (15)	H7A—C7—H7B	109.5
N2—C2—C1	117.89 (14)	H7A—C7—H7C	109.5
C3—C2—C1	121.59 (15)	H7B—C7—H7C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1^i—H1A^i···N2^i	0.98	2.72	3.592	148
C1^i—H1B^i···O1^i	0.98	2.55	3.455	154
C3^i—H3^i···O1^i	0.95	2.41	3.299	155

Symmetry code: (i) −x, y+1/2, −z.