The title compound, C
14H
15N
5O, was synthesized by the reaction of pyrazine-2-carboxylic acid hydrazide with 4-dimethylaminobenzaldehyde in methanol. In the crystal structure, there are intermolecular C—H
O and C—H
N hydrogen bonds. Weak π–π interactions link the molecules into a three-dimensional network.
Supporting information
CCDC reference: 618780
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.133
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.80 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. N1 .. 2.67 Ang.
PLAT737_ALERT_1_C D...A Calc 3.300(3), Rep 3.300(11) ...... 3.67 su-Rat
C6 -O1 1.555 1.655
PLAT756_ALERT_4_C H...A Calc 2.44000, Rep 2.437(9) ...... Senseless su
H6 -O1 1.555 1.655
PLAT756_ALERT_4_C H...A Calc 2.67000, Rep 2.666(5) ...... Senseless su
H2 -N1 1.555 2.675
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 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
5 ALERT type 4 Improvement, methodology, query or suggestion
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.
Pyrazine-2-carboxylic acid (4-dimethylaminobenzylidene)hydrazide
top
Crystal data top
C14H15N5O | F(000) = 284 |
Mr = 269.31 | Dx = 1.356 Mg m−3 |
Triclinic, P1 | Melting point: 526–528K K |
a = 6.049 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.142 (4) Å | Cell parameters from 1050 reflections |
c = 11.047 (4) Å | θ = 2.7–25.5° |
α = 92.547 (6)° | µ = 0.09 mm−1 |
β = 96.063 (6)° | T = 293 K |
γ = 101.286 (6)° | Block, yellow |
V = 659.4 (4) Å3 | 0.22 × 0.20 × 0.16 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2318 independent reflections |
Radiation source: fine-focus sealed tube | 1457 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −6→7 |
Tmin = 0.980, Tmax = 0.986 | k = −12→9 |
3389 measured reflections | l = −13→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0693P)2 + 0.0644P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
2318 reflections | Δρmax = 0.21 e Å−3 |
184 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (5) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3143 (3) | 0.45592 (16) | 0.21830 (16) | 0.0657 (5) | |
N1 | 0.4304 (3) | 0.82022 (19) | 0.05343 (17) | 0.0547 (5) | |
N2 | 0.7656 (3) | 0.66619 (17) | 0.09378 (16) | 0.0462 (5) | |
N3 | 0.6739 (3) | 0.42945 (17) | 0.19563 (16) | 0.0466 (5) | |
H3A | 0.8008 | 0.4653 | 0.1710 | 0.056* | |
N4 | 0.6530 (3) | 0.30524 (17) | 0.24539 (16) | 0.0462 (5) | |
N5 | 0.8602 (3) | −0.26510 (17) | 0.40961 (16) | 0.0473 (5) | |
C1 | 0.8033 (4) | 0.7833 (2) | 0.0424 (2) | 0.0539 (6) | |
H1 | 0.9458 | 0.8149 | 0.0181 | 0.065* | |
C2 | 0.6391 (4) | 0.8596 (2) | 0.0237 (2) | 0.0548 (6) | |
H2 | 0.6759 | 0.9417 | −0.0111 | 0.066* | |
C3 | 0.3923 (4) | 0.7029 (2) | 0.1045 (2) | 0.0503 (6) | |
H3 | 0.2487 | 0.6708 | 0.1271 | 0.060* | |
C4 | 0.5565 (3) | 0.6262 (2) | 0.12551 (18) | 0.0407 (5) | |
C5 | 0.5015 (4) | 0.4955 (2) | 0.18476 (18) | 0.0440 (5) | |
C6 | 0.8269 (4) | 0.2510 (2) | 0.24177 (19) | 0.0442 (5) | |
H6 | 0.9527 | 0.2976 | 0.2092 | 0.053* | |
C7 | 0.8341 (3) | 0.1195 (2) | 0.28673 (18) | 0.0398 (5) | |
C8 | 0.6568 (3) | 0.0452 (2) | 0.34085 (19) | 0.0438 (5) | |
H8 | 0.5285 | 0.0810 | 0.3492 | 0.053* | |
C9 | 0.6661 (3) | −0.0795 (2) | 0.38223 (19) | 0.0439 (5) | |
H9 | 0.5446 | −0.1257 | 0.4186 | 0.053* | |
C10 | 0.8553 (3) | −0.1390 (2) | 0.37091 (17) | 0.0381 (5) | |
C11 | 1.0338 (3) | −0.0634 (2) | 0.31732 (19) | 0.0455 (6) | |
H11 | 1.1627 | −0.0985 | 0.3087 | 0.055* | |
C12 | 1.0230 (3) | 0.0623 (2) | 0.27699 (19) | 0.0454 (6) | |
H12 | 1.1454 | 0.1101 | 0.2424 | 0.054* | |
C13 | 0.6865 (4) | −0.3348 (2) | 0.4782 (2) | 0.0575 (7) | |
H13A | 0.6770 | −0.2793 | 0.5494 | 0.086* | |
H13B | 0.7247 | −0.4180 | 0.5025 | 0.086* | |
H13C | 0.5429 | −0.3532 | 0.4282 | 0.086* | |
C14 | 1.0611 (4) | −0.3219 (2) | 0.4071 (2) | 0.0554 (6) | |
H14A | 1.1110 | −0.3153 | 0.3276 | 0.083* | |
H14B | 1.0266 | −0.4148 | 0.4253 | 0.083* | |
H14C | 1.1790 | −0.2732 | 0.4668 | 0.083* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0561 (11) | 0.0558 (11) | 0.0902 (13) | 0.0114 (8) | 0.0232 (9) | 0.0236 (9) |
N1 | 0.0615 (13) | 0.0463 (12) | 0.0619 (13) | 0.0200 (10) | 0.0111 (10) | 0.0151 (10) |
N2 | 0.0494 (11) | 0.0390 (11) | 0.0525 (11) | 0.0121 (8) | 0.0080 (9) | 0.0098 (9) |
N3 | 0.0537 (11) | 0.0313 (10) | 0.0559 (11) | 0.0076 (8) | 0.0097 (9) | 0.0126 (8) |
N4 | 0.0526 (12) | 0.0341 (10) | 0.0524 (11) | 0.0086 (9) | 0.0064 (9) | 0.0083 (9) |
N5 | 0.0386 (10) | 0.0425 (11) | 0.0655 (12) | 0.0134 (8) | 0.0117 (9) | 0.0164 (9) |
C1 | 0.0532 (14) | 0.0457 (14) | 0.0653 (15) | 0.0103 (11) | 0.0126 (12) | 0.0167 (12) |
C2 | 0.0652 (16) | 0.0400 (13) | 0.0613 (15) | 0.0131 (12) | 0.0073 (12) | 0.0166 (11) |
C3 | 0.0494 (14) | 0.0501 (15) | 0.0549 (14) | 0.0132 (11) | 0.0135 (11) | 0.0097 (11) |
C4 | 0.0476 (13) | 0.0354 (12) | 0.0394 (12) | 0.0096 (10) | 0.0037 (10) | 0.0031 (10) |
C5 | 0.0500 (14) | 0.0370 (12) | 0.0450 (13) | 0.0092 (10) | 0.0056 (10) | 0.0019 (10) |
C6 | 0.0438 (13) | 0.0374 (13) | 0.0496 (13) | 0.0030 (10) | 0.0051 (10) | 0.0061 (10) |
C7 | 0.0370 (12) | 0.0366 (12) | 0.0440 (12) | 0.0051 (9) | 0.0007 (9) | 0.0035 (10) |
C8 | 0.0370 (12) | 0.0389 (13) | 0.0582 (13) | 0.0126 (10) | 0.0072 (10) | 0.0070 (10) |
C9 | 0.0360 (12) | 0.0411 (13) | 0.0569 (13) | 0.0077 (9) | 0.0120 (10) | 0.0126 (10) |
C10 | 0.0358 (11) | 0.0356 (12) | 0.0422 (12) | 0.0075 (9) | 0.0007 (9) | 0.0048 (10) |
C11 | 0.0350 (12) | 0.0483 (14) | 0.0570 (14) | 0.0138 (10) | 0.0097 (10) | 0.0108 (11) |
C12 | 0.0390 (12) | 0.0443 (13) | 0.0532 (13) | 0.0042 (10) | 0.0105 (10) | 0.0119 (11) |
C13 | 0.0510 (14) | 0.0468 (14) | 0.0793 (17) | 0.0125 (11) | 0.0160 (12) | 0.0240 (13) |
C14 | 0.0494 (14) | 0.0508 (15) | 0.0727 (16) | 0.0217 (11) | 0.0110 (12) | 0.0171 (12) |
Geometric parameters (Å, º) top
O1—C5 | 1.227 (2) | C6—C7 | 1.451 (3) |
N1—C2 | 1.328 (3) | C6—H6 | 0.9300 |
N1—C3 | 1.330 (3) | C7—C12 | 1.391 (3) |
N2—C1 | 1.329 (3) | C7—C8 | 1.391 (3) |
N2—C4 | 1.339 (3) | C8—C9 | 1.373 (3) |
N3—C5 | 1.343 (3) | C8—H8 | 0.9300 |
N3—N4 | 1.385 (2) | C9—C10 | 1.409 (3) |
N3—H3A | 0.8600 | C9—H9 | 0.9300 |
N4—C6 | 1.282 (3) | C10—C11 | 1.399 (3) |
N5—C10 | 1.371 (3) | C11—C12 | 1.380 (3) |
N5—C14 | 1.445 (2) | C11—H11 | 0.9300 |
N5—C13 | 1.450 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.378 (3) | C13—H13A | 0.9600 |
C1—H1 | 0.9300 | C13—H13B | 0.9600 |
C2—H2 | 0.9300 | C13—H13C | 0.9600 |
C3—C4 | 1.383 (3) | C14—H14A | 0.9600 |
C3—H3 | 0.9300 | C14—H14B | 0.9600 |
C4—C5 | 1.499 (3) | C14—H14C | 0.9600 |
| | | |
C2—N1—C3 | 115.1 (2) | C8—C7—C6 | 122.60 (19) |
C1—N2—C4 | 115.67 (18) | C9—C8—C7 | 121.79 (19) |
C5—N3—N4 | 121.86 (18) | C9—C8—H8 | 119.1 |
C5—N3—H3A | 119.1 | C7—C8—H8 | 119.1 |
N4—N3—H3A | 119.1 | C8—C9—C10 | 121.54 (18) |
C6—N4—N3 | 114.37 (18) | C8—C9—H9 | 119.2 |
C10—N5—C14 | 121.08 (17) | C10—C9—H9 | 119.2 |
C10—N5—C13 | 121.52 (17) | N5—C10—C11 | 122.55 (18) |
C14—N5—C13 | 116.11 (18) | N5—C10—C9 | 121.05 (18) |
N2—C1—C2 | 122.4 (2) | C11—C10—C9 | 116.40 (19) |
N2—C1—H1 | 118.8 | C12—C11—C10 | 121.45 (19) |
C2—C1—H1 | 118.8 | C12—C11—H11 | 119.3 |
N1—C2—C1 | 122.5 (2) | C10—C11—H11 | 119.3 |
N1—C2—H2 | 118.8 | C11—C12—C7 | 121.80 (19) |
C1—C2—H2 | 118.8 | C11—C12—H12 | 119.1 |
N1—C3—C4 | 123.0 (2) | C7—C12—H12 | 119.1 |
N1—C3—H3 | 118.5 | N5—C13—H13A | 109.5 |
C4—C3—H3 | 118.5 | N5—C13—H13B | 109.5 |
N2—C4—C3 | 121.3 (2) | H13A—C13—H13B | 109.5 |
N2—C4—C5 | 118.73 (19) | N5—C13—H13C | 109.5 |
C3—C4—C5 | 119.97 (19) | H13A—C13—H13C | 109.5 |
O1—C5—N3 | 125.1 (2) | H13B—C13—H13C | 109.5 |
O1—C5—C4 | 121.3 (2) | N5—C14—H14A | 109.5 |
N3—C5—C4 | 113.59 (18) | N5—C14—H14B | 109.5 |
N4—C6—C7 | 122.29 (19) | H14A—C14—H14B | 109.5 |
N4—C6—H6 | 118.9 | N5—C14—H14C | 109.5 |
C7—C6—H6 | 118.9 | H14A—C14—H14C | 109.5 |
C12—C7—C8 | 117.00 (19) | H14B—C14—H14C | 109.5 |
C12—C7—C6 | 120.39 (18) | | |
| | | |
C5—N3—N4—C6 | 175.42 (19) | N4—C6—C7—C12 | 177.65 (19) |
C4—N2—C1—C2 | 0.5 (3) | N4—C6—C7—C8 | −2.4 (3) |
C3—N1—C2—C1 | 1.1 (3) | C12—C7—C8—C9 | −0.4 (3) |
N2—C1—C2—N1 | −1.4 (4) | C6—C7—C8—C9 | 179.60 (19) |
C2—N1—C3—C4 | −0.1 (3) | C7—C8—C9—C10 | −0.6 (3) |
C1—N2—C4—C3 | 0.5 (3) | C14—N5—C10—C11 | 5.8 (3) |
C1—N2—C4—C5 | −179.62 (18) | C13—N5—C10—C11 | 172.3 (2) |
N1—C3—C4—N2 | −0.7 (3) | C14—N5—C10—C9 | −174.97 (19) |
N1—C3—C4—C5 | 179.4 (2) | C13—N5—C10—C9 | −8.4 (3) |
N4—N3—C5—O1 | 1.3 (3) | C8—C9—C10—N5 | −178.25 (19) |
N4—N3—C5—C4 | −178.38 (16) | C8—C9—C10—C11 | 1.1 (3) |
N2—C4—C5—O1 | 178.17 (19) | N5—C10—C11—C12 | 178.76 (19) |
C3—C4—C5—O1 | −1.9 (3) | C9—C10—C11—C12 | −0.5 (3) |
N2—C4—C5—N3 | −2.1 (3) | C10—C11—C12—C7 | −0.5 (3) |
C3—C4—C5—N3 | 177.78 (18) | C8—C7—C12—C11 | 1.0 (3) |
N3—N4—C6—C7 | −178.43 (17) | C6—C7—C12—C11 | −179.08 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.44 (1) | 3.300 (11) | 155 (1) |
C2—H2···N1ii | 0.93 | 2.67 (1) | 3.486 (6) | 148 (1) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z. |