4-Chloro­benzaldehyde (pyrazin-2-ylcarbon­yl)hydrazone

Yuan, C.-C.; Wu, L.; Xing, Z.-Y.; Shi, X.-F.

doi:10.1107/S1600536806026006

4-Chlorobenzaldehyde (pyrazin-2-ylcarbonyl)hydrazone

C.-C. Yuan, L. Wu, Z.-Y. Xing and X.-F. Shi

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026006/bt2126sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026006/bt2126Isup2.hkl Contains datablock I

CCDC reference: 618782

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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

C₁₂H₉ClN₄O	F(000) = 268
M_r = 260.68	D_x = 1.473 Mg m⁻³
Triclinic, P1	Melting point = 479–480 K
a = 5.8860 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.818 (2) Å	Cell parameters from 1017 reflections
c = 13.500 (4) Å	θ = 2.7–25.7°
α = 84.883 (5)°	µ = 0.32 mm⁻¹
β = 80.500 (5)°	T = 293 K
γ = 73.769 (4)°	Block, colourless
V = 587.7 (3) Å³	0.22 × 0.18 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2055 independent reflections
Radiation source: fine-focus sealed tube	1350 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.925, T_max = 0.969	k = −9→9
3000 measured reflections	l = −16→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.044P)² + 0.1868P] where P = (F_o² + 2F_c²)/3
2055 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

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	U_iso*/U_eq
Cl1	0.86529 (15)	−0.25496 (11)	0.97972 (6)	0.0746 (3)
O1	0.0420 (3)	0.3083 (2)	0.46929 (13)	0.0599 (5)
N1	0.0684 (4)	0.6053 (3)	0.19755 (17)	0.0571 (6)
N2	0.4740 (3)	0.4499 (3)	0.29061 (15)	0.0455 (5)
N3	0.4343 (4)	0.2867 (3)	0.47414 (16)	0.0508 (6)
H3A	0.554 (5)	0.311 (4)	0.441 (2)	0.061*
N4	0.4422 (4)	0.1945 (3)	0.56590 (15)	0.0479 (5)
C1	0.4860 (4)	0.5378 (3)	0.20140 (19)	0.0522 (7)
H1	0.6338	0.5489	0.1691	0.063*
C2	0.2867 (5)	0.6125 (3)	0.1555 (2)	0.0529 (7)
H2	0.3053	0.6704	0.0927	0.063*
C3	0.0565 (4)	0.5184 (3)	0.2872 (2)	0.0519 (7)
H3	−0.0923	0.5105	0.3200	0.062*
C4	0.2557 (4)	0.4399 (3)	0.33318 (18)	0.0400 (6)
C5	0.2314 (5)	0.3387 (3)	0.43219 (18)	0.0446 (6)
C6	0.6497 (5)	0.1414 (3)	0.59197 (19)	0.0475 (6)
H6	0.7781	0.1645	0.5481	0.057*
C7	0.6948 (4)	0.0457 (3)	0.68795 (18)	0.0427 (6)
C8	0.5124 (4)	0.0270 (3)	0.76430 (19)	0.0487 (6)
H8	0.3539	0.0776	0.7552	0.058*
C9	0.5636 (5)	−0.0660 (3)	0.85358 (19)	0.0511 (7)
H9	0.4403	−0.0793	0.9039	0.061*
C10	0.7990 (5)	−0.1388 (3)	0.86747 (19)	0.0485 (6)
C11	0.9826 (5)	−0.1205 (4)	0.7936 (2)	0.0547 (7)
H11	1.1409	−0.1706	0.8033	0.066*
C12	0.9299 (5)	−0.0273 (3)	0.7048 (2)	0.0522 (7)
H12	1.0542	−0.0129	0.6554	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0772 (6)	0.0819 (6)	0.0582 (5)	−0.0101 (4)	−0.0222 (4)	0.0172 (4)
O1	0.0577 (12)	0.0717 (13)	0.0549 (12)	−0.0335 (10)	0.0028 (9)	0.0036 (9)
N1	0.0459 (13)	0.0710 (16)	0.0555 (15)	−0.0166 (11)	−0.0157 (11)	0.0100 (12)
N2	0.0392 (12)	0.0512 (13)	0.0452 (12)	−0.0145 (9)	−0.0063 (10)	0.0094 (10)
N3	0.0516 (14)	0.0604 (15)	0.0402 (13)	−0.0224 (11)	0.0000 (11)	0.0110 (11)
N4	0.0556 (14)	0.0517 (13)	0.0365 (12)	−0.0197 (11)	−0.0027 (10)	0.0076 (10)
C1	0.0422 (15)	0.0647 (18)	0.0485 (16)	−0.0177 (13)	−0.0045 (13)	0.0106 (13)
C2	0.0542 (17)	0.0617 (18)	0.0446 (15)	−0.0201 (14)	−0.0133 (13)	0.0133 (13)
C3	0.0385 (14)	0.0639 (18)	0.0535 (16)	−0.0165 (13)	−0.0036 (13)	−0.0002 (14)
C4	0.0379 (13)	0.0403 (14)	0.0423 (14)	−0.0139 (11)	−0.0008 (11)	−0.0027 (11)
C5	0.0472 (15)	0.0457 (15)	0.0428 (15)	−0.0178 (12)	−0.0018 (13)	−0.0034 (12)
C6	0.0492 (16)	0.0526 (16)	0.0418 (14)	−0.0213 (12)	0.0018 (12)	0.0020 (12)
C7	0.0473 (15)	0.0440 (15)	0.0406 (14)	−0.0193 (12)	−0.0053 (12)	−0.0013 (11)
C8	0.0401 (14)	0.0561 (17)	0.0493 (16)	−0.0135 (12)	−0.0079 (12)	0.0045 (12)
C9	0.0478 (16)	0.0592 (17)	0.0452 (15)	−0.0173 (13)	−0.0029 (12)	0.0057 (13)
C10	0.0522 (16)	0.0462 (16)	0.0465 (15)	−0.0112 (12)	−0.0111 (13)	0.0011 (12)
C11	0.0407 (15)	0.0617 (18)	0.0607 (18)	−0.0084 (13)	−0.0142 (14)	−0.0017 (14)
C12	0.0421 (15)	0.0619 (18)	0.0527 (16)	−0.0174 (13)	0.0008 (13)	−0.0063 (13)

Geometric parameters (Å, º) top

Cl1—C10	1.739 (3)	C3—H3	0.9300
O1—C5	1.222 (3)	C4—C5	1.498 (3)
N1—C2	1.330 (3)	C6—C7	1.463 (3)
N1—C3	1.335 (3)	C6—H6	0.9300
N2—C1	1.334 (3)	C7—C12	1.390 (3)
N2—C4	1.339 (3)	C7—C8	1.390 (3)
N3—C5	1.350 (3)	C8—C9	1.383 (3)
N3—N4	1.378 (3)	C8—H8	0.9300
N3—H3A	0.83 (3)	C9—C10	1.380 (3)
N4—C6	1.272 (3)	C9—H9	0.9300
C1—C2	1.376 (3)	C10—C11	1.374 (4)
C1—H1	0.9300	C11—C12	1.380 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.381 (3)	C12—H12	0.9300

C2—N1—C3	115.2 (2)	N4—C6—C7	122.9 (2)
C1—N2—C4	115.9 (2)	N4—C6—H6	118.6
C5—N3—N4	121.5 (2)	C7—C6—H6	118.6
C5—N3—H3A	117 (2)	C12—C7—C8	118.2 (2)
N4—N3—H3A	122 (2)	C12—C7—C6	118.9 (2)
C6—N4—N3	114.4 (2)	C8—C7—C6	122.9 (2)
N2—C1—C2	122.1 (2)	C9—C8—C7	120.9 (2)
N2—C1—H1	118.9	C9—C8—H8	119.6
C2—C1—H1	118.9	C7—C8—H8	119.6
N1—C2—C1	122.6 (2)	C10—C9—C8	119.5 (2)
N1—C2—H2	118.7	C10—C9—H9	120.3
C1—C2—H2	118.7	C8—C9—H9	120.3
N1—C3—C4	122.8 (2)	C11—C10—C9	120.8 (2)
N1—C3—H3	118.6	C11—C10—Cl1	119.4 (2)
C4—C3—H3	118.6	C9—C10—Cl1	119.8 (2)
N2—C4—C3	121.4 (2)	C10—C11—C12	119.3 (2)
N2—C4—C5	118.4 (2)	C10—C11—H11	120.3
C3—C4—C5	120.2 (2)	C12—C11—H11	120.3
O1—C5—N3	124.7 (2)	C11—C12—C7	121.3 (2)
O1—C5—C4	121.3 (2)	C11—C12—H12	119.3
N3—C5—C4	113.9 (2)	C7—C12—H12	119.3

C5—N3—N4—C6	174.4 (2)	C3—C4—C5—N3	−172.7 (2)
C4—N2—C1—C2	−0.4 (4)	N3—N4—C6—C7	178.2 (2)
C3—N1—C2—C1	−0.7 (4)	N4—C6—C7—C12	171.8 (2)
N2—C1—C2—N1	1.3 (4)	N4—C6—C7—C8	−9.4 (4)
C2—N1—C3—C4	−0.5 (4)	C12—C7—C8—C9	−1.7 (4)
C1—N2—C4—C3	−0.8 (4)	C6—C7—C8—C9	179.5 (2)
C1—N2—C4—C5	178.4 (2)	C7—C8—C9—C10	0.9 (4)
N1—C3—C4—N2	1.4 (4)	C8—C9—C10—C11	−0.3 (4)
N1—C3—C4—C5	−177.8 (2)	C8—C9—C10—Cl1	179.70 (19)
N4—N3—C5—O1	−1.0 (4)	C9—C10—C11—C12	0.4 (4)
N4—N3—C5—C4	179.1 (2)	Cl1—C10—C11—C12	−179.5 (2)
N2—C4—C5—O1	−171.9 (2)	C10—C11—C12—C7	−1.3 (4)
C3—C4—C5—O1	7.3 (4)	C8—C7—C12—C11	1.9 (4)
N2—C4—C5—N3	8.1 (3)	C6—C7—C12—C11	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2	0.83 (3)	2.27 (3)	2.689 (3)	111 (2)
C6—H6···O1ⁱ	0.93	2.24 (3)	3.133 (3)	160 (2)

Symmetry code: (i) x+1, y, z.

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4-Chloro­benzaldehyde (pyrazin-2-ylcarbon­yl)hydrazone

Supporting information

Key indicators

checkCIF/PLATON results

4-Chlorobenzaldehyde (pyrazin-2-ylcarbonyl)hydrazone