N′-(2-Chloro­benzyl­idene)pyrazine-2-carbohydrazide

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.

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

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Computing details

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

Crystal data

C12H9ClN4O	Dx = 1.492 Mg m^−3
Mr = 260.68	Melting point = 492–495 K
Monoclinic, Pn	Mo Kα radiation, λ = 0.71070 Å
a = 6.7912 (12) Å	Cell parameters from 1698 reflections
b = 3.8852 (8) Å	θ = 1.9–27.9°
c = 22.113 (4) Å	µ = 0.32 mm^−1
β = 95.999 (9)°	T = 294 K
V = 580.25 (19) Å^3	Block, colorless
Z = 2	0.22 × 0.18 × 0.16 mm
F(000) = 268

Data collection

Rigaku Saturn diffractometer	2589 independent reflections
Radiation source: rotating anode	1970 reflections with I > 2σ(I)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.032
φ and ω scans	θmax = 27.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.933, Tmax = 0.950	k = −3→5
4795 measured reflections	l = −29→29

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0979P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2589 reflections	Δρmax = 0.29 e Å^−3
167 parameters	Δρmin = −0.31 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1203 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.58385 (13)	0.6529 (3)	0.63141 (5)	0.0531 (3)
O1	0.7753 (4)	1.0620 (9)	0.94094 (13)	0.0553 (8)
N1	1.1845 (4)	0.5941 (8)	0.89704 (13)	0.0393 (7)
N2	1.3235 (5)	0.6986 (9)	1.01884 (15)	0.0511 (9)
N3	0.8248 (5)	0.8137 (9)	0.85123 (16)	0.0429 (8)
N4	0.6461 (4)	0.9191 (8)	0.82152 (14)	0.0395 (7)
C1	1.0757 (5)	0.7552 (10)	0.93508 (16)	0.0333 (7)
C2	1.1413 (5)	0.8065 (10)	0.99513 (17)	0.0440 (9)
H2	1.0594	0.9173	1.0202	0.053*
C3	1.4310 (5)	0.5445 (11)	0.98091 (18)	0.0451 (9)
H3	1.5572	0.4698	0.9954	0.054*
C4	1.3646 (5)	0.4881 (10)	0.92012 (16)	0.0411 (8)
H4	1.4461	0.3755	0.8952	0.049*
C5	0.8763 (5)	0.8935 (9)	0.91035 (16)	0.0355 (7)
C6	0.6086 (5)	0.8103 (9)	0.76765 (18)	0.0401 (8)
H6	0.6998	0.6694	0.7511	0.048*
C7	0.4228 (5)	0.9028 (9)	0.73060 (17)	0.0373 (8)
C8	0.3959 (6)	0.8386 (8)	0.66793 (18)	0.0397 (8)
C9	0.2228 (6)	0.9356 (11)	0.63304 (19)	0.0509 (10)
H9	0.2096	0.8986	0.5913	0.061*
C10	0.0721 (6)	1.0853 (11)	0.65986 (19)	0.0492 (10)
H10	−0.0445	1.1464	0.6365	0.059*
C11	0.0929 (6)	1.1467 (11)	0.7225 (2)	0.0483 (9)
H11	−0.0091	1.2495	0.7410	0.058*
C12	0.2668 (5)	1.0531 (10)	0.75692 (18)	0.0448 (8)
H12	0.2794	1.0918	0.7986	0.054*
H1	0.908 (8)	0.753 (13)	0.829 (3)	0.059 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0578 (6)	0.0577 (5)	0.0452 (5)	−0.0005 (5)	0.0112 (4)	−0.0033 (5)
O1	0.0395 (15)	0.078 (2)	0.0481 (16)	0.0195 (14)	0.0017 (12)	−0.0123 (15)
N1	0.0317 (15)	0.0531 (18)	0.0322 (15)	0.0065 (13)	−0.0007 (11)	0.0011 (13)
N2	0.0439 (19)	0.068 (2)	0.0388 (17)	0.0107 (16)	−0.0081 (14)	−0.0072 (16)
N3	0.0303 (16)	0.057 (2)	0.0391 (17)	0.0130 (14)	−0.0074 (13)	−0.0020 (14)
N4	0.0318 (15)	0.0451 (16)	0.0391 (15)	0.0061 (12)	−0.0084 (12)	0.0023 (13)
C1	0.0285 (15)	0.0366 (16)	0.0348 (17)	0.0022 (12)	0.0034 (13)	0.0014 (13)
C2	0.0358 (19)	0.057 (2)	0.0372 (19)	0.0096 (16)	−0.0037 (14)	−0.0049 (16)
C3	0.0306 (18)	0.056 (2)	0.047 (2)	0.0058 (16)	−0.0052 (15)	0.0053 (18)
C4	0.0321 (18)	0.047 (2)	0.044 (2)	0.0076 (15)	0.0036 (14)	0.0017 (16)
C5	0.0303 (17)	0.0365 (18)	0.0384 (17)	0.0037 (13)	−0.0028 (13)	0.0018 (14)
C6	0.0353 (18)	0.0371 (18)	0.046 (2)	0.0063 (15)	−0.0037 (15)	0.0040 (15)
C7	0.0310 (17)	0.0367 (17)	0.0415 (19)	−0.0028 (13)	−0.0092 (14)	0.0022 (15)
C8	0.044 (2)	0.0330 (17)	0.041 (2)	−0.0066 (15)	−0.0013 (15)	0.0017 (14)
C9	0.052 (2)	0.056 (2)	0.041 (2)	−0.0113 (19)	−0.0143 (18)	0.0040 (18)
C10	0.037 (2)	0.054 (2)	0.053 (2)	−0.0040 (17)	−0.0126 (17)	0.0103 (17)
C11	0.0333 (19)	0.052 (2)	0.058 (2)	0.0028 (15)	−0.0017 (17)	0.0006 (17)
C12	0.0367 (19)	0.050 (2)	0.045 (2)	0.0030 (16)	−0.0041 (15)	−0.0008 (17)

Geometric parameters (Å, º)

Cl1—C8	1.737 (4)	C3—H3	0.9300
O1—C5	1.206 (4)	C4—H4	0.9300
N1—C1	1.332 (5)	C6—C7	1.475 (5)
N1—C4	1.340 (4)	C6—H6	0.9300
N2—C3	1.312 (5)	C7—C12	1.390 (5)
N2—C2	1.359 (5)	C7—C8	1.401 (5)
N3—C5	1.354 (5)	C8—C9	1.389 (5)
N3—N4	1.380 (4)	C9—C10	1.366 (7)
N3—H1	0.82 (6)	C9—H9	0.9300
N4—C6	1.264 (5)	C10—C11	1.399 (6)
C1—C2	1.370 (5)	C10—H10	0.9300
C1—C5	1.506 (5)	C11—C12	1.384 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.390 (5)	C12—H12	0.9300
C1—N1—C4	116.6 (3)	N4—C6—C7	121.2 (3)
C3—N2—C2	116.0 (3)	N4—C6—H6	119.4
C5—N3—N4	121.1 (3)	C7—C6—H6	119.4
C5—N3—H1	121 (4)	C12—C7—C8	117.6 (3)
N4—N3—H1	115 (4)	C12—C7—C6	121.0 (3)
C6—N4—N3	115.5 (3)	C8—C7—C6	121.4 (3)
N1—C1—C2	122.3 (3)	C9—C8—C7	121.1 (4)
N1—C1—C5	118.4 (3)	C9—C8—Cl1	118.3 (3)
C2—C1—C5	119.3 (3)	C7—C8—Cl1	120.5 (3)
N2—C2—C1	121.3 (3)	C10—C9—C8	120.2 (4)
N2—C2—H2	119.3	C10—C9—H9	119.9
C1—C2—H2	119.3	C8—C9—H9	119.9
N2—C3—C4	123.0 (3)	C9—C10—C11	120.0 (4)
N2—C3—H3	118.5	C9—C10—H10	120.0
C4—C3—H3	118.5	C11—C10—H10	120.0
N1—C4—C3	120.7 (3)	C12—C11—C10	119.4 (4)
N1—C4—H4	119.7	C12—C11—H11	120.3
C3—C4—H4	119.7	C10—C11—H11	120.3
O1—C5—N3	124.2 (3)	C11—C12—C7	121.6 (4)
O1—C5—C1	122.2 (3)	C11—C12—H12	119.2
N3—C5—C1	113.6 (3)	C7—C12—H12	119.2
C5—N3—N4—C6	−175.5 (4)	N3—N4—C6—C7	180.0 (3)
C4—N1—C1—C2	−1.1 (6)	N4—C6—C7—C12	−13.0 (6)
C4—N1—C1—C5	177.2 (3)	N4—C6—C7—C8	167.9 (3)
C3—N2—C2—C1	0.1 (6)	C12—C7—C8—C9	2.8 (5)
N1—C1—C2—N2	0.9 (6)	C6—C7—C8—C9	−178.1 (3)
C5—C1—C2—N2	−177.3 (4)	C12—C7—C8—Cl1	179.8 (3)
C2—N2—C3—C4	−0.8 (7)	C6—C7—C8—Cl1	−1.1 (5)
C1—N1—C4—C3	0.3 (6)	C7—C8—C9—C10	−2.4 (6)
N2—C3—C4—N1	0.7 (7)	Cl1—C8—C9—C10	−179.4 (3)
N4—N3—C5—O1	−1.1 (6)	C8—C9—C10—C11	1.1 (6)
N4—N3—C5—C1	179.7 (3)	C9—C10—C11—C12	−0.3 (6)
N1—C1—C5—O1	−174.9 (4)	C10—C11—C12—C7	0.8 (6)
C2—C1—C5—O1	3.4 (6)	C8—C7—C12—C11	−2.0 (6)
N1—C1—C5—N3	4.4 (5)	C6—C7—C12—C11	178.9 (4)
C2—C1—C5—N3	−177.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N1	0.82 (6)	2.36 (6)	2.684 (3)	104 (5)
C3—H3···O1A	0.93	2.55 (1)	3.193 (3)	126 (1)