In the structure of methyl 5-methyl-2-pyrazinecarboxylate, C
7H
8N
2O
2, 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).
Supporting information
CCDC reference: 1560429
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, clear colourless |
Z = 2 | 0.66 × 0.65 × 0.56 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.0328P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1i—H1Ai···N2i | 0.98 | 2.72 | 3.592 | 148 |
C1i—H1Bi···O1i | 0.98 | 2.55 | 3.455 | 154 |
C3i—H3i···O1i | 0.95 | 2.41 | 3.299 | 155 |
Symmetry code: (i) −x, y+1/2, −z. |