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The title compound, C12H9ClN4O, was prepared by the reaction of pyrazine-2-carboxylic acid hydrazide and 2-chlorobenzaldehyde in methanol. In the crystal structure, there are intra­molecular N—H...N and inter­molecular C—H...O hydrogen bonds. Weak π–π stacking inter­actions are also observed between two parallel mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043212/bt2206sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043212/bt2206Isup2.hkl
Contains datablock I

CCDC reference: 627358

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.164
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... O1A H3 O1A PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... O1A C3 O1A PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... O1A C3 H3 O1A
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.93 From the CIF: _reflns_number_total 2589 Count of symmetry unique reflns 1386 Completeness (_total/calc) 186.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1203 Fraction of Friedel pairs measured 0.868 Are heavy atom types Z>Si present yes PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 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 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

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalClear; software used to prepare material for publication: SHELXL97.

N'-(2-Chlorobenzylidene)pyrazine-2-carbohydrazide top
Crystal data top
C12H9ClN4ODx = 1.492 Mg m3
Mr = 260.68Melting point = 492–495 K
Monoclinic, PnMo Kα radiation, λ = 0.71070 Å
a = 6.7912 (12) ÅCell parameters from 1698 reflections
b = 3.8852 (8) Åθ = 1.9–27.9°
c = 22.113 (4) ŵ = 0.32 mm1
β = 95.999 (9)°T = 294 K
V = 580.25 (19) Å3Block, colorless
Z = 20.22 × 0.18 × 0.16 mm
F(000) = 268
Data collection top
Rigaku Saturn
diffractometer
2589 independent reflections
Radiation source: rotating anode1970 reflections with I > 2σ(I)
Detector resolution: 7.31 pixels mm-1Rint = 0.032
φ and ω scansθmax = 27.9°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.933, Tmax = 0.950k = 35
4795 measured reflectionsl = 2929
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0979P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2589 reflectionsΔρmax = 0.29 e Å3
167 parametersΔρmin = 0.31 e Å3
2 restraintsAbsolute structure: Flack (1983), 1203 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (10)
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
Cl10.58385 (13)0.6529 (3)0.63141 (5)0.0531 (3)
O10.7753 (4)1.0620 (9)0.94094 (13)0.0553 (8)
N11.1845 (4)0.5941 (8)0.89704 (13)0.0393 (7)
N21.3235 (5)0.6986 (9)1.01884 (15)0.0511 (9)
N30.8248 (5)0.8137 (9)0.85123 (16)0.0429 (8)
N40.6461 (4)0.9191 (8)0.82152 (14)0.0395 (7)
C11.0757 (5)0.7552 (10)0.93508 (16)0.0333 (7)
C21.1413 (5)0.8065 (10)0.99513 (17)0.0440 (9)
H21.05940.91731.02020.053*
C31.4310 (5)0.5445 (11)0.98091 (18)0.0451 (9)
H31.55720.46980.99540.054*
C41.3646 (5)0.4881 (10)0.92012 (16)0.0411 (8)
H41.44610.37550.89520.049*
C50.8763 (5)0.8935 (9)0.91035 (16)0.0355 (7)
C60.6086 (5)0.8103 (9)0.76765 (18)0.0401 (8)
H60.69980.66940.75110.048*
C70.4228 (5)0.9028 (9)0.73060 (17)0.0373 (8)
C80.3959 (6)0.8386 (8)0.66793 (18)0.0397 (8)
C90.2228 (6)0.9356 (11)0.63304 (19)0.0509 (10)
H90.20960.89860.59130.061*
C100.0721 (6)1.0853 (11)0.65986 (19)0.0492 (10)
H100.04451.14640.63650.059*
C110.0929 (6)1.1467 (11)0.7225 (2)0.0483 (9)
H110.00911.24950.74100.058*
C120.2668 (5)1.0531 (10)0.75692 (18)0.0448 (8)
H120.27941.09180.79860.054*
H10.908 (8)0.753 (13)0.829 (3)0.059 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0578 (6)0.0577 (5)0.0452 (5)0.0005 (5)0.0112 (4)0.0033 (5)
O10.0395 (15)0.078 (2)0.0481 (16)0.0195 (14)0.0017 (12)0.0123 (15)
N10.0317 (15)0.0531 (18)0.0322 (15)0.0065 (13)0.0007 (11)0.0011 (13)
N20.0439 (19)0.068 (2)0.0388 (17)0.0107 (16)0.0081 (14)0.0072 (16)
N30.0303 (16)0.057 (2)0.0391 (17)0.0130 (14)0.0074 (13)0.0020 (14)
N40.0318 (15)0.0451 (16)0.0391 (15)0.0061 (12)0.0084 (12)0.0023 (13)
C10.0285 (15)0.0366 (16)0.0348 (17)0.0022 (12)0.0034 (13)0.0014 (13)
C20.0358 (19)0.057 (2)0.0372 (19)0.0096 (16)0.0037 (14)0.0049 (16)
C30.0306 (18)0.056 (2)0.047 (2)0.0058 (16)0.0052 (15)0.0053 (18)
C40.0321 (18)0.047 (2)0.044 (2)0.0076 (15)0.0036 (14)0.0017 (16)
C50.0303 (17)0.0365 (18)0.0384 (17)0.0037 (13)0.0028 (13)0.0018 (14)
C60.0353 (18)0.0371 (18)0.046 (2)0.0063 (15)0.0037 (15)0.0040 (15)
C70.0310 (17)0.0367 (17)0.0415 (19)0.0028 (13)0.0092 (14)0.0022 (15)
C80.044 (2)0.0330 (17)0.041 (2)0.0066 (15)0.0013 (15)0.0017 (14)
C90.052 (2)0.056 (2)0.041 (2)0.0113 (19)0.0143 (18)0.0040 (18)
C100.037 (2)0.054 (2)0.053 (2)0.0040 (17)0.0126 (17)0.0103 (17)
C110.0333 (19)0.052 (2)0.058 (2)0.0028 (15)0.0017 (17)0.0006 (17)
C120.0367 (19)0.050 (2)0.045 (2)0.0030 (16)0.0041 (15)0.0008 (17)
Geometric parameters (Å, º) top
Cl1—C81.737 (4)C3—H30.9300
O1—C51.206 (4)C4—H40.9300
N1—C11.332 (5)C6—C71.475 (5)
N1—C41.340 (4)C6—H60.9300
N2—C31.312 (5)C7—C121.390 (5)
N2—C21.359 (5)C7—C81.401 (5)
N3—C51.354 (5)C8—C91.389 (5)
N3—N41.380 (4)C9—C101.366 (7)
N3—H10.82 (6)C9—H90.9300
N4—C61.264 (5)C10—C111.399 (6)
C1—C21.370 (5)C10—H100.9300
C1—C51.506 (5)C11—C121.384 (5)
C2—H20.9300C11—H110.9300
C3—C41.390 (5)C12—H120.9300
C1—N1—C4116.6 (3)N4—C6—C7121.2 (3)
C3—N2—C2116.0 (3)N4—C6—H6119.4
C5—N3—N4121.1 (3)C7—C6—H6119.4
C5—N3—H1121 (4)C12—C7—C8117.6 (3)
N4—N3—H1115 (4)C12—C7—C6121.0 (3)
C6—N4—N3115.5 (3)C8—C7—C6121.4 (3)
N1—C1—C2122.3 (3)C9—C8—C7121.1 (4)
N1—C1—C5118.4 (3)C9—C8—Cl1118.3 (3)
C2—C1—C5119.3 (3)C7—C8—Cl1120.5 (3)
N2—C2—C1121.3 (3)C10—C9—C8120.2 (4)
N2—C2—H2119.3C10—C9—H9119.9
C1—C2—H2119.3C8—C9—H9119.9
N2—C3—C4123.0 (3)C9—C10—C11120.0 (4)
N2—C3—H3118.5C9—C10—H10120.0
C4—C3—H3118.5C11—C10—H10120.0
N1—C4—C3120.7 (3)C12—C11—C10119.4 (4)
N1—C4—H4119.7C12—C11—H11120.3
C3—C4—H4119.7C10—C11—H11120.3
O1—C5—N3124.2 (3)C11—C12—C7121.6 (4)
O1—C5—C1122.2 (3)C11—C12—H12119.2
N3—C5—C1113.6 (3)C7—C12—H12119.2
C5—N3—N4—C6175.5 (4)N3—N4—C6—C7180.0 (3)
C4—N1—C1—C21.1 (6)N4—C6—C7—C1213.0 (6)
C4—N1—C1—C5177.2 (3)N4—C6—C7—C8167.9 (3)
C3—N2—C2—C10.1 (6)C12—C7—C8—C92.8 (5)
N1—C1—C2—N20.9 (6)C6—C7—C8—C9178.1 (3)
C5—C1—C2—N2177.3 (4)C12—C7—C8—Cl1179.8 (3)
C2—N2—C3—C40.8 (7)C6—C7—C8—Cl11.1 (5)
C1—N1—C4—C30.3 (6)C7—C8—C9—C102.4 (6)
N2—C3—C4—N10.7 (7)Cl1—C8—C9—C10179.4 (3)
N4—N3—C5—O11.1 (6)C8—C9—C10—C111.1 (6)
N4—N3—C5—C1179.7 (3)C9—C10—C11—C120.3 (6)
N1—C1—C5—O1174.9 (4)C10—C11—C12—C70.8 (6)
C2—C1—C5—O13.4 (6)C8—C7—C12—C112.0 (6)
N1—C1—C5—N34.4 (5)C6—C7—C12—C11178.9 (4)
C2—C1—C5—N3177.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1···N10.82 (6)2.36 (6)2.684 (3)104 (5)
C3—H3···O1A0.932.55 (1)3.193 (3)126 (1)
 

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