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The title compound, C12H9ClN4O, was prepared by the reaction of pyrazine-2-carboxylic acid hydrazide and 4-chloro­benzaldehyde in methanol. In the crystal structure, there is an intra­molecular N—H...N hydrogen bond, forming a five-membered ring, and an inter­molecular C—H...O hydrogen bond, resulting in a one-dimensional infinite chain along the a axis. Weak face-to-face π–π stacking inter­actions are also observed between two anti­parallel mol­ecules. These π–π stacking inter­actions further join the mol­ecules into a three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026006/bt2126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026006/bt2126Isup2.hkl
Contains datablock I

CCDC reference: 618782

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.107
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C 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 PLAT756_ALERT_4_C H...A Calc 2.24000, Rep 2.24(3) ...... Senseless su H6 -O1 1.555 1.655
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

4-Chlorobenzaldehyde (pyrazine-2-carbonyl)hydrazone top
Crystal data top
C12H9ClN4OF(000) = 268
Mr = 260.68Dx = 1.473 Mg m3
Triclinic, P1Melting point = 479–480 K
a = 5.8860 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.818 (2) ÅCell parameters from 1017 reflections
c = 13.500 (4) Åθ = 2.7–25.7°
α = 84.883 (5)°µ = 0.32 mm1
β = 80.500 (5)°T = 293 K
γ = 73.769 (4)°Block, colourless
V = 587.7 (3) Å30.22 × 0.18 × 0.10 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2055 independent reflections
Radiation source: fine-focus sealed tube1350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.925, Tmax = 0.969k = 99
3000 measured reflectionsl = 1612
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.044P)2 + 0.1868P]
where P = (Fo2 + 2Fc2)/3
2055 reflections(Δ/σ)max < 0.001
166 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
Cl10.86529 (15)0.25496 (11)0.97972 (6)0.0746 (3)
O10.0420 (3)0.3083 (2)0.46929 (13)0.0599 (5)
N10.0684 (4)0.6053 (3)0.19755 (17)0.0571 (6)
N20.4740 (3)0.4499 (3)0.29061 (15)0.0455 (5)
N30.4343 (4)0.2867 (3)0.47414 (16)0.0508 (6)
H3A0.554 (5)0.311 (4)0.441 (2)0.061*
N40.4422 (4)0.1945 (3)0.56590 (15)0.0479 (5)
C10.4860 (4)0.5378 (3)0.20140 (19)0.0522 (7)
H10.63380.54890.16910.063*
C20.2867 (5)0.6125 (3)0.1555 (2)0.0529 (7)
H20.30530.67040.09270.063*
C30.0565 (4)0.5184 (3)0.2872 (2)0.0519 (7)
H30.09230.51050.32000.062*
C40.2557 (4)0.4399 (3)0.33318 (18)0.0400 (6)
C50.2314 (5)0.3387 (3)0.43219 (18)0.0446 (6)
C60.6497 (5)0.1414 (3)0.59197 (19)0.0475 (6)
H60.77810.16450.54810.057*
C70.6948 (4)0.0457 (3)0.68795 (18)0.0427 (6)
C80.5124 (4)0.0270 (3)0.76430 (19)0.0487 (6)
H80.35390.07760.75520.058*
C90.5636 (5)0.0660 (3)0.85358 (19)0.0511 (7)
H90.44030.07930.90390.061*
C100.7990 (5)0.1388 (3)0.86747 (19)0.0485 (6)
C110.9826 (5)0.1205 (4)0.7936 (2)0.0547 (7)
H111.14090.17060.80330.066*
C120.9299 (5)0.0273 (3)0.7048 (2)0.0522 (7)
H121.05420.01290.65540.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0772 (6)0.0819 (6)0.0582 (5)0.0101 (4)0.0222 (4)0.0172 (4)
O10.0577 (12)0.0717 (13)0.0549 (12)0.0335 (10)0.0028 (9)0.0036 (9)
N10.0459 (13)0.0710 (16)0.0555 (15)0.0166 (11)0.0157 (11)0.0100 (12)
N20.0392 (12)0.0512 (13)0.0452 (12)0.0145 (9)0.0063 (10)0.0094 (10)
N30.0516 (14)0.0604 (15)0.0402 (13)0.0224 (11)0.0000 (11)0.0110 (11)
N40.0556 (14)0.0517 (13)0.0365 (12)0.0197 (11)0.0027 (10)0.0076 (10)
C10.0422 (15)0.0647 (18)0.0485 (16)0.0177 (13)0.0045 (13)0.0106 (13)
C20.0542 (17)0.0617 (18)0.0446 (15)0.0201 (14)0.0133 (13)0.0133 (13)
C30.0385 (14)0.0639 (18)0.0535 (16)0.0165 (13)0.0036 (13)0.0002 (14)
C40.0379 (13)0.0403 (14)0.0423 (14)0.0139 (11)0.0008 (11)0.0027 (11)
C50.0472 (15)0.0457 (15)0.0428 (15)0.0178 (12)0.0018 (13)0.0034 (12)
C60.0492 (16)0.0526 (16)0.0418 (14)0.0213 (12)0.0018 (12)0.0020 (12)
C70.0473 (15)0.0440 (15)0.0406 (14)0.0193 (12)0.0053 (12)0.0013 (11)
C80.0401 (14)0.0561 (17)0.0493 (16)0.0135 (12)0.0079 (12)0.0045 (12)
C90.0478 (16)0.0592 (17)0.0452 (15)0.0173 (13)0.0029 (12)0.0057 (13)
C100.0522 (16)0.0462 (16)0.0465 (15)0.0112 (12)0.0111 (13)0.0011 (12)
C110.0407 (15)0.0617 (18)0.0607 (18)0.0084 (13)0.0142 (14)0.0017 (14)
C120.0421 (15)0.0619 (18)0.0527 (16)0.0174 (13)0.0008 (13)0.0063 (13)
Geometric parameters (Å, º) top
Cl1—C101.739 (3)C3—H30.9300
O1—C51.222 (3)C4—C51.498 (3)
N1—C21.330 (3)C6—C71.463 (3)
N1—C31.335 (3)C6—H60.9300
N2—C11.334 (3)C7—C121.390 (3)
N2—C41.339 (3)C7—C81.390 (3)
N3—C51.350 (3)C8—C91.383 (3)
N3—N41.378 (3)C8—H80.9300
N3—H3A0.83 (3)C9—C101.380 (3)
N4—C61.272 (3)C9—H90.9300
C1—C21.376 (3)C10—C111.374 (4)
C1—H10.9300C11—C121.380 (4)
C2—H20.9300C11—H110.9300
C3—C41.381 (3)C12—H120.9300
C2—N1—C3115.2 (2)N4—C6—C7122.9 (2)
C1—N2—C4115.9 (2)N4—C6—H6118.6
C5—N3—N4121.5 (2)C7—C6—H6118.6
C5—N3—H3A117 (2)C12—C7—C8118.2 (2)
N4—N3—H3A122 (2)C12—C7—C6118.9 (2)
C6—N4—N3114.4 (2)C8—C7—C6122.9 (2)
N2—C1—C2122.1 (2)C9—C8—C7120.9 (2)
N2—C1—H1118.9C9—C8—H8119.6
C2—C1—H1118.9C7—C8—H8119.6
N1—C2—C1122.6 (2)C10—C9—C8119.5 (2)
N1—C2—H2118.7C10—C9—H9120.3
C1—C2—H2118.7C8—C9—H9120.3
N1—C3—C4122.8 (2)C11—C10—C9120.8 (2)
N1—C3—H3118.6C11—C10—Cl1119.4 (2)
C4—C3—H3118.6C9—C10—Cl1119.8 (2)
N2—C4—C3121.4 (2)C10—C11—C12119.3 (2)
N2—C4—C5118.4 (2)C10—C11—H11120.3
C3—C4—C5120.2 (2)C12—C11—H11120.3
O1—C5—N3124.7 (2)C11—C12—C7121.3 (2)
O1—C5—C4121.3 (2)C11—C12—H12119.3
N3—C5—C4113.9 (2)C7—C12—H12119.3
C5—N3—N4—C6174.4 (2)C3—C4—C5—N3172.7 (2)
C4—N2—C1—C20.4 (4)N3—N4—C6—C7178.2 (2)
C3—N1—C2—C10.7 (4)N4—C6—C7—C12171.8 (2)
N2—C1—C2—N11.3 (4)N4—C6—C7—C89.4 (4)
C2—N1—C3—C40.5 (4)C12—C7—C8—C91.7 (4)
C1—N2—C4—C30.8 (4)C6—C7—C8—C9179.5 (2)
C1—N2—C4—C5178.4 (2)C7—C8—C9—C100.9 (4)
N1—C3—C4—N21.4 (4)C8—C9—C10—C110.3 (4)
N1—C3—C4—C5177.8 (2)C8—C9—C10—Cl1179.70 (19)
N4—N3—C5—O11.0 (4)C9—C10—C11—C120.4 (4)
N4—N3—C5—C4179.1 (2)Cl1—C10—C11—C12179.5 (2)
N2—C4—C5—O1171.9 (2)C10—C11—C12—C71.3 (4)
C3—C4—C5—O17.3 (4)C8—C7—C12—C111.9 (4)
N2—C4—C5—N38.1 (3)C6—C7—C12—C11179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N20.83 (3)2.27 (3)2.689 (3)111 (2)
C6—H6···O1i0.932.24 (3)3.133 (3)160 (2)
Symmetry code: (i) x+1, y, z.
 

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