(5-Methyl­isoxazol-3-yl)[2-(5-methyl­isoxazol-3-yl)-2,3-dihydro-1H-isoindol-1-yl­idene]amine

The title compound, C₁₆H₁₄N₄O₂, was synthesized by the reaction of o-phthalaldehyde and 5-methyl-4,5-dihydro­isoxazol-3-ylamine in dichloro­methane. The conformation of the mol­ecular structure may be influenced by a weak intra­molecular C—H...N inter­action and weak C—H...π inter­actions, and π–π stacking inter­actions may influence the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.121
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A   ..  CG4     ..       2.96 Ang.

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

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

---

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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(5-Methylisoxazol-3-yl)[2-(5-methylisoxazol-3-yl)-2,3-dihydro-1H-isoindol- 1-ylidene]amine

Crystal data

C16H14N4O2	F(000) = 616
Mr = 294.31	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14155 reflections
a = 13.5698 (8) Å	θ = 1.5–28.0°
b = 7.8257 (6) Å	µ = 0.09 mm^−1
c = 13.6527 (8) Å	T = 296 K
β = 100.690 (4)°	Prism with corners rounded, colorless
V = 1424.66 (16) Å^3	0.44 × 0.36 × 0.29 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2807 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2318 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.095
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.960, Tmax = 0.973	l = −16→16
11079 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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.1431P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2807 reflections	Δρmax = 0.18 e Å^−3
202 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.60409 (8)	0.74654 (15)	0.36931 (9)	0.0594 (4)
O2	0.08452 (8)	0.19055 (14)	0.29499 (8)	0.0573 (4)
N1	0.38605 (9)	0.67101 (15)	0.46086 (9)	0.0463 (4)
N2	0.53635 (10)	0.78016 (18)	0.43446 (11)	0.0574 (5)
N3	0.29351 (9)	0.44381 (16)	0.38240 (9)	0.0486 (4)
N4	0.14513 (11)	0.33696 (18)	0.29085 (11)	0.0583 (5)
C1	0.24372 (11)	0.61626 (18)	0.52258 (10)	0.0434 (4)
C2	0.15476 (11)	0.5504 (2)	0.54415 (11)	0.0494 (5)
C3	0.11273 (12)	0.6309 (2)	0.61703 (12)	0.0559 (5)
C4	0.15759 (13)	0.7740 (2)	0.66624 (12)	0.0575 (5)
C5	0.24591 (13)	0.8397 (2)	0.64464 (12)	0.0558 (5)
C6	0.28883 (12)	0.75785 (19)	0.57272 (11)	0.0474 (4)
C7	0.38427 (12)	0.79993 (19)	0.53818 (12)	0.0506 (5)
C8	0.30461 (10)	0.56066 (17)	0.44862 (10)	0.0415 (4)
C9	0.46501 (11)	0.66698 (17)	0.40956 (11)	0.0437 (4)
C10	0.48239 (11)	0.55895 (19)	0.33155 (11)	0.0475 (4)
C11	0.56964 (11)	0.61459 (19)	0.30997 (11)	0.0481 (4)
C12	0.63160 (13)	0.5625 (2)	0.23648 (13)	0.0611 (6)
C13	0.21420 (10)	0.32813 (17)	0.37080 (10)	0.0423 (4)
C14	0.20269 (12)	0.18136 (19)	0.42790 (11)	0.0485 (4)
C15	0.12200 (11)	0.10147 (18)	0.37786 (10)	0.0439 (4)
C16	0.06870 (13)	−0.0596 (2)	0.39254 (12)	0.0572 (5)
H2	0.12440	0.45520	0.51060	0.0590*
H3	0.05380	0.58830	0.63310	0.0670*
H4	0.12790	0.82660	0.71450	0.0690*
H5	0.27560	0.93600	0.67750	0.0670*
H7A	0.38260	0.91460	0.51100	0.0610*
H7B	0.44180	0.78890	0.59180	0.0610*
H10	0.44250	0.46960	0.30190	0.0570*
H12A	0.70130	0.57050	0.26630	0.0920*
H12B	0.61780	0.63650	0.17950	0.0920*
H12C	0.61590	0.44680	0.21600	0.0920*
H14	0.24280	0.14770	0.48760	0.0580*
H16A	−0.00230	−0.04250	0.37310	0.0860*
H16B	0.08420	−0.09210	0.46150	0.0860*
H16C	0.08980	−0.14840	0.35250	0.0860*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0457 (6)	0.0618 (7)	0.0731 (7)	−0.0132 (5)	0.0173 (5)	−0.0066 (6)
O2	0.0515 (6)	0.0588 (7)	0.0564 (6)	−0.0135 (5)	−0.0032 (5)	0.0097 (5)
N1	0.0426 (6)	0.0447 (7)	0.0525 (7)	−0.0062 (5)	0.0112 (5)	−0.0058 (5)
N2	0.0470 (7)	0.0570 (8)	0.0707 (9)	−0.0108 (6)	0.0172 (6)	−0.0097 (7)
N3	0.0472 (7)	0.0482 (7)	0.0524 (7)	−0.0092 (5)	0.0147 (6)	−0.0075 (5)
N4	0.0529 (8)	0.0557 (8)	0.0628 (8)	−0.0129 (6)	0.0020 (6)	0.0124 (6)
C1	0.0441 (7)	0.0419 (7)	0.0440 (7)	0.0023 (6)	0.0078 (6)	0.0004 (6)
C2	0.0487 (8)	0.0483 (8)	0.0522 (8)	−0.0021 (6)	0.0122 (6)	−0.0027 (6)
C3	0.0534 (9)	0.0612 (9)	0.0568 (9)	0.0024 (7)	0.0198 (7)	0.0002 (7)
C4	0.0633 (10)	0.0603 (9)	0.0523 (8)	0.0064 (8)	0.0194 (8)	−0.0058 (7)
C5	0.0606 (10)	0.0531 (9)	0.0531 (8)	0.0019 (7)	0.0090 (7)	−0.0098 (7)
C6	0.0483 (8)	0.0463 (8)	0.0471 (7)	0.0006 (6)	0.0073 (6)	−0.0021 (6)
C7	0.0497 (8)	0.0458 (8)	0.0555 (8)	−0.0039 (6)	0.0077 (7)	−0.0083 (6)
C8	0.0401 (7)	0.0397 (7)	0.0443 (7)	−0.0005 (5)	0.0070 (6)	0.0024 (6)
C9	0.0389 (7)	0.0419 (7)	0.0492 (7)	−0.0017 (5)	0.0057 (6)	0.0038 (6)
C10	0.0435 (7)	0.0474 (8)	0.0522 (8)	−0.0064 (6)	0.0104 (6)	−0.0010 (6)
C11	0.0426 (7)	0.0494 (8)	0.0520 (8)	−0.0018 (6)	0.0083 (6)	0.0062 (6)
C12	0.0526 (9)	0.0711 (11)	0.0632 (10)	−0.0015 (8)	0.0201 (8)	0.0057 (8)
C13	0.0405 (7)	0.0428 (7)	0.0453 (7)	−0.0024 (5)	0.0122 (6)	−0.0072 (6)
C14	0.0464 (8)	0.0519 (8)	0.0454 (7)	−0.0050 (6)	0.0041 (6)	0.0019 (6)
C15	0.0442 (7)	0.0434 (7)	0.0449 (7)	−0.0007 (6)	0.0103 (6)	−0.0027 (6)
C16	0.0584 (9)	0.0515 (9)	0.0611 (9)	−0.0100 (7)	0.0099 (8)	0.0008 (7)

Geometric parameters (Å, º)

O1—N2	1.4173 (18)	C10—C11	1.345 (2)
O1—C11	1.3419 (19)	C11—C12	1.481 (2)
O2—N4	1.4176 (18)	C13—C14	1.413 (2)
O2—C15	1.3458 (17)	C14—C15	1.334 (2)
N1—C7	1.464 (2)	C15—C16	1.485 (2)
N1—C8	1.3880 (18)	C2—H2	0.9300
N1—C9	1.385 (2)	C3—H3	0.9300
N2—C9	1.310 (2)	C4—H4	0.9300
N3—C8	1.2750 (18)	C5—H5	0.9300
N3—C13	1.3927 (18)	C7—H7A	0.9700
N4—C13	1.302 (2)	C7—H7B	0.9700
C1—C2	1.393 (2)	C10—H10	0.9300
C1—C6	1.384 (2)	C12—H12A	0.9600
C1—C8	1.484 (2)	C12—H12B	0.9600
C2—C3	1.387 (2)	C12—H12C	0.9600
C3—C4	1.387 (2)	C14—H14	0.9300
C4—C5	1.385 (2)	C16—H16A	0.9600
C5—C6	1.388 (2)	C16—H16B	0.9600
C6—C7	1.495 (2)	C16—H16C	0.9600
C9—C10	1.414 (2)
O1···H10^i	2.8900	C13···H12B^v	2.9200
O1···H14^ii	2.7000	C14···H2	2.7300
O2···H3^iii	2.8600	C14···H12B^v	3.0900
O2···H4^iii	2.8600	H2···C13	2.6400
N3···C10	2.920 (2)	H2···C14	2.7300
N2···H7A	2.7100	H3···O2^iii	2.8600
N2···H12C^i	2.9300	H4···O2^iii	2.8600
N2···H7A^iv	2.6800	H4···H16A^iii	2.5400
N2···H7B	2.7000	H4···N4^x	2.8300
N3···H10	2.4800	H4···H16C^ix	2.4700
N3···H12B^v	2.8900	H5···N3^x	2.9200
N3···H5^vi	2.9200	H7A···N2	2.7100
N4···H16A^vii	2.8400	H7A···N2^iv	2.6800
N4···H4^vi	2.8300	H7B···N2	2.7000
C1···C11^ii	3.572 (2)	H7B···C10^ii	3.0300
C2···C13	3.160 (2)	H7B···H12B^x	2.5300
C2···C14	3.416 (2)	H10···N3	2.4800
C10···N3	2.920 (2)	H10···C8	3.0700
C11···C1^ii	3.572 (2)	H10···O1^v	2.8900
C12···C14^i	3.582 (2)	H12A···C2^ii	3.0900
C12···C13^i	3.462 (2)	H12B···N3^i	2.8900
C13···C12^v	3.462 (2)	H12B···C13^i	2.9200
C13···C2	3.160 (2)	H12B···C14^i	3.0900
C14···C2	3.416 (2)	H12B···H7B^vi	2.5300
C14···C12^v	3.582 (2)	H12C···N2^v	2.9300
C2···H12A^ii	3.0900	H12C···C9^v	2.8700
C3···H16B^viii	3.0100	H14···O1^ii	2.7000
C4···H16A^iii	2.9500	H16A···N4^xi	2.8400
C4···H16C^ix	3.0200	H16A···C4^iii	2.9500
C4···H16B^viii	2.9800	H16A···H4^iii	2.5400
C5···H16B^viii	3.0500	H16B···C3^xii	3.0100
C8···H10	3.0700	H16B···C4^xii	2.9800
C9···H12C^i	2.8700	H16B···C5^xii	3.0500
C10···H7B^ii	3.0300	H16C···C4^xiii	3.0200
C13···H2	2.6400	H16C···H4^xiii	2.4700
N2—O1—C11	109.14 (12)	O2—C15—C14	109.52 (13)
N4—O2—C15	108.70 (11)	O2—C15—C16	115.82 (13)
C7—N1—C8	113.35 (12)	C14—C15—C16	134.65 (14)
C7—N1—C9	119.89 (12)	C1—C2—H2	121.00
C8—N1—C9	126.75 (12)	C3—C2—H2	121.00
O1—N2—C9	104.23 (12)	C2—C3—H3	120.00
C8—N3—C13	122.27 (12)	C4—C3—H3	120.00
O2—N4—C13	104.86 (12)	C3—C4—H4	119.00
C2—C1—C6	120.84 (14)	C5—C4—H4	119.00
C2—C1—C8	130.47 (13)	C4—C5—H5	121.00
C6—C1—C8	108.68 (13)	C6—C5—H5	121.00
C1—C2—C3	118.13 (14)	N1—C7—H7A	111.00
C2—C3—C4	120.82 (15)	N1—C7—H7B	111.00
C3—C4—C5	121.05 (15)	C6—C7—H7A	111.00
C4—C5—C6	118.20 (15)	C6—C7—H7B	111.00
C1—C6—C5	120.95 (15)	H7A—C7—H7B	109.00
C1—C6—C7	110.48 (13)	C9—C10—H10	128.00
C5—C6—C7	128.56 (14)	C11—C10—H10	128.00
N1—C7—C6	101.94 (12)	C11—C12—H12A	109.00
N1—C8—N3	121.22 (13)	C11—C12—H12B	109.00
N1—C8—C1	105.49 (11)	C11—C12—H12C	110.00
N3—C8—C1	133.27 (13)	H12A—C12—H12B	109.00
N1—C9—N2	117.21 (13)	H12A—C12—H12C	109.00
N1—C9—C10	130.36 (13)	H12B—C12—H12C	109.00
N2—C9—C10	112.43 (14)	C13—C14—H14	127.00
C9—C10—C11	104.37 (13)	C15—C14—H14	127.00
O1—C11—C10	109.83 (13)	C15—C16—H16A	109.00
O1—C11—C12	116.29 (13)	C15—C16—H16B	109.00
C10—C11—C12	133.88 (14)	C15—C16—H16C	109.00
N3—C13—N4	118.80 (13)	H16A—C16—H16B	110.00
N3—C13—C14	128.89 (13)	H16A—C16—H16C	109.00
N4—C13—C14	111.69 (13)	H16B—C16—H16C	109.00
C13—C14—C15	105.23 (13)
C11—O1—N2—C9	−0.48 (16)	C6—C1—C2—C3	0.1 (2)
N2—O1—C11—C12	179.77 (13)	C2—C1—C6—C5	−1.1 (2)
N2—O1—C11—C10	0.34 (17)	C6—C1—C8—N3	−176.58 (15)
N4—O2—C15—C16	−178.41 (13)	C8—C1—C2—C3	−178.88 (14)
C15—O2—N4—C13	−0.43 (16)	C2—C1—C8—N1	−179.11 (15)
N4—O2—C15—C14	0.33 (16)	C8—C1—C6—C5	178.15 (14)
C9—N1—C7—C6	−179.91 (13)	C6—C1—C8—N1	1.79 (15)
C8—N1—C7—C6	−0.85 (16)	C8—C1—C6—C7	−2.40 (17)
C7—N1—C8—C1	−0.50 (15)	C2—C1—C8—N3	2.5 (3)
C7—N1—C9—N2	0.9 (2)	C1—C2—C3—C4	0.7 (2)
C8—N1—C9—N2	−178.03 (14)	C2—C3—C4—C5	−0.5 (2)
C7—N1—C9—C10	−178.52 (15)	C3—C4—C5—C6	−0.4 (2)
C8—N1—C9—C10	2.6 (2)	C4—C5—C6—C1	1.2 (2)
C9—N1—C8—C1	178.48 (13)	C4—C5—C6—C7	−178.17 (15)
C7—N1—C8—N3	178.11 (13)	C5—C6—C7—N1	−178.61 (15)
C9—N1—C8—N3	−2.9 (2)	C1—C6—C7—N1	2.00 (16)
O1—N2—C9—C10	0.44 (17)	N1—C9—C10—C11	179.18 (15)
O1—N2—C9—N1	−179.07 (12)	N2—C9—C10—C11	−0.25 (18)
C13—N3—C8—C1	−3.9 (2)	C9—C10—C11—C12	−179.36 (17)
C13—N3—C8—N1	177.90 (12)	C9—C10—C11—O1	−0.07 (17)
C8—N3—C13—N4	111.47 (16)	N3—C13—C14—C15	−170.94 (14)
C8—N3—C13—C14	−78.4 (2)	N4—C13—C14—C15	−0.19 (18)
O2—N4—C13—C14	0.38 (17)	C13—C14—C15—C16	178.30 (16)
O2—N4—C13—N3	172.17 (12)	C13—C14—C15—O2	−0.10 (17)
C2—C1—C6—C7	178.40 (13)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N3	0.93	2.48	2.920 (2)	109
C2—H2···Cg2	0.93	2.88	3.6348 (17)	139
C12—H12A···Cg4^ii	0.96	2.96	3.5516 (18)	121
C16—H16B···Cg4^xii	0.96	2.74	3.5597 (18)	144

Symmetry codes: (ii) −x+1, −y+1, −z+1; (xii) x, y−1, z.