(2-Chloro­pyridin-3-yl)(4-nitro­benzyl­idene)­amine

In the title compound, C₁₂H₈ClN₃O₂, the dihedral angle between the least-squares planes of the pyridine and benzene rings is 20.8 (1)°. In the crystal structure, mol­ecules pack nearly parallel along the a axis, with some π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.079
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.72 mm

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           26.00
           From the CIF: _reflns_number_total               2280
           Count of symmetry unique reflns         1337
           Completeness (_total/calc)            170.53%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       943
           Fraction of Friedel pairs measured     0.705
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2-Chloropyridin-3-yl)(4-nitrobenzylidene)amine

Crystal data

C12H8ClN3O2	F(000) = 536
Mr = 261.66	Dx = 1.494 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1966 reflections
a = 7.1404 (6) Å	θ = 2.3–29.0°
b = 11.9642 (11) Å	µ = 0.33 mm^−1
c = 13.6188 (16) Å	T = 296 K
V = 1163.4 (2) Å^3	Stick, yellow
Z = 4	0.72 × 0.32 × 0.11 mm

Data collection

Stoe IPDS-II diffractometer	2280 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1887 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.048
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −9→9
Absorption correction: integration X-RED (Stoe & Cie, 2002)	k = −16→16
Tmin = 0.800, Tmax = 0.965	l = −18→18
11387 measured reflections

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)] = 0.040	H-atom parameters not refined
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0274P)^2 + 0.1715P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2280 reflections	Δρmax = 0.10 e Å^−3
163 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Absolute structure: Flack (1983), 943 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.23 (8)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.58661 (12)	0.45386 (6)	0.60392 (5)	0.0690 (2)
O1	0.6915 (4)	0.8353 (2)	0.07377 (14)	0.0995 (10)
O2	0.6614 (3)	1.00800 (19)	0.11340 (15)	0.0844 (9)
N1	0.6282 (3)	0.51615 (18)	0.78487 (14)	0.0584 (8)
N2	0.6532 (3)	0.69074 (16)	0.56495 (13)	0.0431 (6)
N3	0.6678 (3)	0.9083 (2)	0.13390 (15)	0.0619 (9)
C1	0.6246 (3)	0.5538 (2)	0.69398 (16)	0.0465 (7)
C2	0.6460 (3)	0.66462 (19)	0.66643 (15)	0.0411 (7)
C3	0.6729 (4)	0.7407 (2)	0.74115 (18)	0.0550 (9)
C4	0.6782 (4)	0.7035 (3)	0.83719 (18)	0.0629 (10)
C5	0.6570 (4)	0.5917 (2)	0.85480 (18)	0.0615 (10)
C6	0.5993 (3)	0.78602 (18)	0.53504 (15)	0.0433 (7)
C7	0.6145 (3)	0.81630 (18)	0.43090 (15)	0.0413 (7)
C8	0.6552 (3)	0.7358 (2)	0.36038 (17)	0.0475 (8)
C9	0.6718 (4)	0.7654 (2)	0.26308 (18)	0.0525 (8)
C10	0.6475 (3)	0.8760 (2)	0.23766 (16)	0.0466 (8)
C11	0.6070 (4)	0.9571 (2)	0.30514 (16)	0.0506 (7)
C12	0.5909 (3)	0.92652 (17)	0.40257 (16)	0.0469 (7)
H3	0.68730	0.81630	0.72710	0.0660*
H4	0.69580	0.75350	0.88870	0.0750*
H5	0.66310	0.56710	0.91950	0.0740*
H6	0.54980	0.83710	0.57950	0.0520*
H8	0.67120	0.66160	0.37900	0.0570*
H9	0.69880	0.71200	0.21550	0.0630*
H11	0.59070	1.03110	0.28590	0.0610*
H12	0.56380	0.98050	0.44960	0.0560*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1000 (5)	0.0500 (3)	0.0569 (3)	−0.0085 (4)	−0.0079 (4)	0.0025 (3)
O1	0.151 (2)	0.1074 (18)	0.0401 (11)	0.0288 (16)	0.0018 (13)	−0.0024 (12)
O2	0.1146 (18)	0.0857 (15)	0.0529 (11)	−0.0151 (13)	−0.0014 (12)	0.0266 (11)
N1	0.0652 (15)	0.0670 (14)	0.0431 (11)	−0.0003 (11)	−0.0005 (11)	0.0153 (10)
N2	0.0452 (11)	0.0460 (10)	0.0381 (9)	−0.0015 (9)	−0.0011 (8)	0.0045 (8)
N3	0.0625 (15)	0.0830 (17)	0.0402 (12)	−0.0017 (13)	−0.0045 (10)	0.0057 (12)
C1	0.0460 (14)	0.0515 (13)	0.0419 (11)	0.0014 (12)	−0.0003 (10)	0.0060 (11)
C2	0.0369 (12)	0.0518 (13)	0.0345 (11)	0.0025 (10)	0.0032 (9)	0.0055 (9)
C3	0.0651 (17)	0.0550 (14)	0.0449 (13)	0.0034 (13)	−0.0008 (13)	−0.0010 (12)
C4	0.0700 (19)	0.0778 (19)	0.0408 (14)	0.0028 (16)	0.0012 (13)	−0.0078 (13)
C5	0.0636 (18)	0.084 (2)	0.0368 (12)	0.0029 (15)	0.0036 (12)	0.0157 (14)
C6	0.0434 (12)	0.0475 (12)	0.0390 (11)	0.0013 (11)	0.0015 (12)	0.0033 (9)
C7	0.0363 (11)	0.0485 (12)	0.0392 (11)	−0.0007 (10)	−0.0023 (10)	0.0058 (10)
C8	0.0548 (16)	0.0423 (12)	0.0454 (12)	0.0027 (11)	−0.0048 (11)	0.0038 (10)
C9	0.0564 (16)	0.0575 (15)	0.0435 (13)	0.0061 (12)	−0.0021 (12)	−0.0063 (12)
C10	0.0456 (14)	0.0575 (14)	0.0366 (11)	−0.0030 (11)	−0.0019 (10)	0.0076 (10)
C11	0.0547 (14)	0.0488 (12)	0.0483 (12)	−0.0035 (13)	−0.0029 (12)	0.0124 (12)
C12	0.0535 (14)	0.0444 (11)	0.0429 (11)	0.0019 (11)	0.0040 (12)	0.0007 (9)

Geometric parameters (Å, º)

Cl1—C1	1.734 (2)	C7—C12	1.384 (3)
O1—N3	1.209 (3)	C8—C9	1.377 (3)
O2—N3	1.226 (3)	C9—C10	1.379 (3)
N1—C1	1.318 (3)	C10—C11	1.367 (3)
N1—C5	1.329 (3)	C11—C12	1.381 (3)
N2—C2	1.418 (3)	C3—H3	0.9300
N2—C6	1.270 (3)	C4—H4	0.9300
N3—C10	1.472 (3)	C5—H5	0.9300
C1—C2	1.386 (3)	C6—H6	0.9300
C2—C3	1.379 (3)	C8—H8	0.9300
C3—C4	1.382 (4)	C9—H9	0.9300
C4—C5	1.367 (4)	C11—H11	0.9300
C6—C7	1.468 (3)	C12—H12	0.9300
C7—C8	1.391 (3)
Cl1···N2	2.922 (2)	C9···C3^viii	3.579 (4)
Cl1···C4^i	3.632 (3)	C9···C3^ix	3.564 (4)
Cl1···O1^ii	3.437 (2)	C11···C1^ix	3.447 (4)
Cl1···H9^iii	2.9300	C12···C2^ix	3.488 (3)
Cl1···H5^iv	3.0900	C12···C1^ix	3.588 (3)
Cl1···H4^i	3.1300	C3···H6	2.6400
O1···Cl1^v	3.437 (2)	C6···H3	2.7100
O2···C6^vi	3.183 (3)	C8···H6^viii	3.0600
O1···H4^vii	2.7000	H3···C6	2.7100
O1···H9	2.4300	H3···H6	2.2500
O2···H11	2.4200	H3···O2^xi	2.8300
O2···H3^vi	2.8300	H3···H11^xi	2.5500
O2···H6^vi	2.8100	H4···O1^xii	2.7000
N2···C7^viii	3.295 (3)	H4···Cl1^x	3.1300
N2···Cl1	2.922 (2)	H5···Cl1^iii	3.0900
N1···H8^iii	2.8700	H6···C3	2.6400
N2···H8	2.5600	H6···H3	2.2500
C1···C11^viii	3.447 (4)	H6···H12	2.4700
C1···C12^viii	3.588 (3)	H6···O2^xi	2.8100
C2···C12^viii	3.488 (3)	H6···C8^ix	3.0600
C3···C9^ix	3.579 (4)	H8···N2	2.5600
C3···C9^viii	3.564 (4)	H8···N1^iv	2.8700
C4···Cl1^x	3.632 (3)	H9···O1	2.4300
C6···C8^ix	3.486 (3)	H9···Cl1^iv	2.9300
C6···O2^xi	3.183 (3)	H11···O2	2.4200
C7···N2^ix	3.295 (3)	H11···H3^vi	2.5500
C8···C6^viii	3.486 (3)	H12···H6	2.4700
C1—N1—C5	116.3 (2)	N3—C10—C11	118.7 (2)
C2—N2—C6	119.96 (19)	C9—C10—C11	122.6 (2)
O1—N3—O2	123.6 (2)	C10—C11—C12	118.4 (2)
O1—N3—C10	118.3 (2)	C7—C12—C11	120.7 (2)
O2—N3—C10	118.1 (2)	C2—C3—H3	120.00
Cl1—C1—N1	115.58 (18)	C4—C3—H3	120.00
Cl1—C1—C2	119.03 (17)	C3—C4—H4	121.00
N1—C1—C2	125.4 (2)	C5—C4—H4	121.00
N2—C2—C1	118.59 (19)	N1—C5—H5	118.00
N2—C2—C3	124.7 (2)	C4—C5—H5	118.00
C1—C2—C3	116.6 (2)	N2—C6—H6	120.00
C2—C3—C4	119.3 (2)	C7—C6—H6	120.00
C3—C4—C5	118.6 (3)	C7—C8—H8	120.00
N1—C5—C4	123.8 (2)	C9—C8—H8	120.00
N2—C6—C7	120.59 (19)	C8—C9—H9	121.00
C6—C7—C8	120.8 (2)	C10—C9—H9	121.00
C6—C7—C12	119.70 (19)	C10—C11—H11	121.00
C8—C7—C12	119.5 (2)	C12—C11—H11	121.00
C7—C8—C9	120.3 (2)	C7—C12—H12	120.00
C8—C9—C10	118.5 (2)	C11—C12—H12	120.00
N3—C10—C9	118.7 (2)
C5—N1—C1—Cl1	−179.94 (19)	C1—C2—C3—C4	0.4 (4)
C5—N1—C1—C2	−0.8 (4)	C2—C3—C4—C5	0.2 (4)
C1—N1—C5—C4	1.5 (4)	C3—C4—C5—N1	−1.2 (4)
C6—N2—C2—C1	152.2 (2)	N2—C6—C7—C8	11.9 (3)
C6—N2—C2—C3	−33.0 (4)	N2—C6—C7—C12	−167.2 (2)
C2—N2—C6—C7	177.0 (2)	C6—C7—C8—C9	−179.1 (2)
O2—N3—C10—C9	−174.0 (2)	C8—C7—C12—C11	0.1 (3)
O1—N3—C10—C11	−175.3 (3)	C12—C7—C8—C9	−0.1 (3)
O1—N3—C10—C9	5.3 (3)	C6—C7—C12—C11	179.2 (2)
O2—N3—C10—C11	5.4 (3)	C7—C8—C9—C10	0.1 (4)
N1—C1—C2—N2	175.2 (2)	C8—C9—C10—N3	179.1 (2)
N1—C1—C2—C3	−0.1 (3)	C8—C9—C10—C11	−0.2 (4)
Cl1—C1—C2—C3	179.01 (19)	N3—C10—C11—C12	−179.1 (2)
Cl1—C1—C2—N2	−5.7 (3)	C9—C10—C11—C12	0.3 (4)
N2—C2—C3—C4	−174.6 (2)	C10—C11—C12—C7	−0.3 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+3/2, −y+1, z+1/2; (iv) −x+3/2, −y+1, z−1/2; (v) −x+1, y+1/2, −z+1/2; (vi) −x+3/2, −y+2, z−1/2; (vii) x, y, z−1; (viii) x+1/2, −y+3/2, −z+1; (ix) x−1/2, −y+3/2, −z+1; (x) −x+1, y+1/2, −z+3/2; (xi) −x+3/2, −y+2, z+1/2; (xii) x, y, z+1.