N-[4-(4-Nitro­benzyl­ideneamino)phen­yl]acetamide

The title compund, C₁₅H₁₃N₃O₃, was synthesized by the solid-state reaction of 4-nitro­benzaldehyde and 4-amino-N-methyl­benzamide. The mol­ecules are linked head-to-tail into zigzag chains along the c axis by N—H...O hydrogen bonds. The mol­ecules are further linked into sheets, parallel to (100), which are stacked in columns along [100].

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.063
• wR factor = 0.142
• Data-to-parameter ratio = 12.6

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 .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   N1      ..       5.10 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku, 2002); 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: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N-(4-(4-nitrobenzylideneamino)phenyl)acetamide

Crystal data

C15H13N3O3	Dx = 1.439 Mg m^−3
Mr = 283.28	Melting point: 497 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
a = 7.0477 (8) Å	Cell parameters from 7894 reflections
b = 15.1868 (17) Å	θ = 3.0–25.4°
c = 24.426 (3) Å	µ = 0.10 mm^−1
V = 2614.4 (5) Å^3	T = 153 K
Z = 8	Block, yellow
F(000) = 1184	0.38 × 0.28 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer	2392 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (Jacobson, 1998)	h = −8→8
Tmin = 0.962, Tmax = 0.980	k = −18→18
23604 measured reflections	l = −29→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 2.827P] where P = (Fo^2 + 2Fc^2)/3
2392 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

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
O1	0.3086 (3)	0.07263 (12)	0.67188 (7)	0.0363 (5)
O2	0.3856 (3)	−0.03098 (12)	0.61546 (8)	0.0385 (5)
O3	0.4621 (3)	0.71569 (11)	0.29691 (7)	0.0348 (5)
N1	0.3465 (3)	0.04611 (14)	0.62565 (8)	0.0285 (5)
N2	0.3429 (3)	0.37099 (13)	0.45248 (8)	0.0242 (5)
N3	0.3848 (3)	0.58092 (12)	0.26271 (8)	0.0237 (5)
H3B	0.3595	0.5529	0.2320	0.028*
C1	0.3482 (3)	0.22741 (15)	0.49499 (9)	0.0224 (5)
C2	0.3512 (3)	0.13726 (15)	0.48497 (10)	0.0253 (5)
H2A	0.3561	0.1165	0.4483	0.030*
C3	0.3471 (3)	0.07745 (15)	0.52765 (10)	0.0260 (5)
H3A	0.3459	0.0159	0.5208	0.031*
C4	0.3449 (3)	0.10956 (15)	0.58038 (9)	0.0227 (5)
C5	0.3440 (3)	0.19894 (16)	0.59231 (9)	0.0243 (5)
H5A	0.3436	0.2191	0.6291	0.029*
C6	0.3438 (3)	0.25790 (16)	0.54911 (9)	0.0245 (5)
H6A	0.3406	0.3194	0.5562	0.029*
C7	0.3521 (3)	0.28737 (16)	0.44817 (9)	0.0247 (5)
H7A	0.3619	0.2627	0.4125	0.030*
C8	0.3469 (3)	0.42199 (15)	0.40380 (9)	0.0220 (5)
C9	0.2770 (3)	0.39398 (15)	0.35312 (9)	0.0234 (5)
H9A	0.2205	0.3374	0.3500	0.028*
C10	0.2892 (3)	0.44732 (15)	0.30780 (9)	0.0235 (5)
H10A	0.2417	0.4270	0.2737	0.028*
C11	0.3703 (3)	0.53090 (15)	0.31132 (9)	0.0214 (5)
C12	0.4357 (3)	0.56071 (15)	0.36204 (9)	0.0247 (5)
H12A	0.4892	0.6179	0.3654	0.030*
C13	0.4221 (3)	0.50630 (15)	0.40751 (9)	0.0244 (5)
H13A	0.4653	0.5272	0.4420	0.029*
C14	0.4334 (3)	0.66774 (15)	0.25763 (10)	0.0243 (5)
C15	0.4494 (4)	0.70047 (17)	0.19978 (10)	0.0312 (6)
H15A	0.4858	0.7627	0.2000	0.047*
H15B	0.3268	0.6938	0.1813	0.047*
H15C	0.5459	0.6662	0.1803	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0448 (11)	0.0451 (11)	0.0189 (9)	−0.0038 (9)	0.0022 (8)	0.0053 (8)
O2	0.0442 (11)	0.0277 (10)	0.0435 (11)	0.0062 (9)	0.0038 (9)	0.0108 (8)
O3	0.0503 (12)	0.0246 (9)	0.0294 (10)	−0.0047 (8)	−0.0047 (8)	−0.0007 (8)
N1	0.0248 (11)	0.0327 (12)	0.0279 (12)	−0.0024 (9)	−0.0016 (9)	0.0078 (9)
N2	0.0265 (10)	0.0254 (11)	0.0207 (10)	0.0001 (8)	0.0007 (8)	0.0021 (8)
N3	0.0301 (11)	0.0224 (10)	0.0187 (10)	−0.0020 (8)	−0.0001 (8)	−0.0011 (8)
C1	0.0200 (11)	0.0252 (12)	0.0218 (12)	−0.0006 (9)	0.0001 (9)	0.0004 (10)
C2	0.0288 (12)	0.0272 (12)	0.0199 (11)	0.0004 (10)	0.0006 (10)	−0.0025 (10)
C3	0.0300 (13)	0.0211 (12)	0.0268 (13)	0.0002 (10)	0.0019 (10)	−0.0008 (10)
C4	0.0218 (11)	0.0250 (12)	0.0211 (12)	−0.0002 (10)	0.0002 (9)	0.0042 (10)
C5	0.0260 (12)	0.0295 (13)	0.0175 (11)	−0.0007 (10)	0.0001 (9)	−0.0021 (10)
C6	0.0254 (12)	0.0225 (12)	0.0254 (12)	0.0002 (10)	−0.0005 (10)	−0.0022 (10)
C7	0.0256 (12)	0.0287 (13)	0.0196 (11)	0.0013 (10)	0.0018 (10)	−0.0010 (10)
C8	0.0229 (12)	0.0222 (12)	0.0209 (12)	0.0037 (10)	0.0011 (9)	0.0003 (9)
C9	0.0254 (12)	0.0201 (11)	0.0247 (12)	0.0013 (10)	0.0017 (10)	−0.0002 (10)
C10	0.0268 (12)	0.0238 (12)	0.0199 (12)	−0.0019 (10)	−0.0007 (10)	−0.0032 (9)
C11	0.0228 (11)	0.0221 (11)	0.0193 (11)	0.0024 (9)	0.0011 (9)	0.0005 (9)
C12	0.0294 (13)	0.0210 (11)	0.0238 (12)	−0.0015 (10)	−0.0025 (10)	−0.0018 (9)
C13	0.0294 (12)	0.0241 (12)	0.0198 (11)	0.0018 (10)	−0.0013 (10)	−0.0026 (9)
C14	0.0245 (12)	0.0231 (11)	0.0251 (13)	0.0008 (10)	−0.0026 (10)	0.0021 (10)
C15	0.0367 (14)	0.0283 (13)	0.0285 (13)	−0.0014 (11)	−0.0019 (11)	0.0065 (11)

Geometric parameters (Å, º)

O1—N1	1.228 (3)	C5—H5A	0.9500
O2—N1	1.228 (3)	C6—H6A	0.9500
O3—C14	1.221 (3)	C7—H7A	0.9500
N1—C4	1.467 (3)	C8—C13	1.389 (3)
N2—C7	1.276 (3)	C8—C9	1.399 (3)
N2—C8	1.419 (3)	C9—C10	1.374 (3)
N3—C14	1.368 (3)	C9—H9A	0.9500
N3—C11	1.413 (3)	C10—C11	1.395 (3)
N3—H3B	0.8800	C10—H10A	0.9500
C1—C2	1.391 (3)	C11—C12	1.397 (3)
C1—C6	1.401 (3)	C12—C13	1.388 (3)
C1—C7	1.462 (3)	C12—H12A	0.9500
C2—C3	1.383 (3)	C13—H13A	0.9500
C2—H2A	0.9500	C14—C15	1.502 (3)
C3—C4	1.377 (3)	C15—H15A	0.9800
C3—H3A	0.9500	C15—H15B	0.9800
C4—C5	1.388 (3)	C15—H15C	0.9800
C5—C6	1.384 (3)
O2—N1—O1	123.2 (2)	C13—C8—C9	118.2 (2)
O2—N1—C4	118.4 (2)	C13—C8—N2	117.1 (2)
O1—N1—C4	118.4 (2)	C9—C8—N2	124.6 (2)
C7—N2—C8	118.2 (2)	C10—C9—C8	120.8 (2)
C14—N3—C11	127.77 (19)	C10—C9—H9A	119.6
C14—N3—H3B	116.1	C8—C9—H9A	119.6
C11—N3—H3B	116.1	C9—C10—C11	120.8 (2)
C2—C1—C6	119.4 (2)	C9—C10—H10A	119.6
C2—C1—C7	118.4 (2)	C11—C10—H10A	119.6
C6—C1—C7	122.2 (2)	C10—C11—C12	119.0 (2)
C3—C2—C1	120.9 (2)	C10—C11—N3	117.9 (2)
C3—C2—H2A	119.5	C12—C11—N3	123.2 (2)
C1—C2—H2A	119.5	C13—C12—C11	119.6 (2)
C4—C3—C2	118.2 (2)	C13—C12—H12A	120.2
C4—C3—H3A	120.9	C11—C12—H12A	120.2
C2—C3—H3A	120.9	C12—C13—C8	121.5 (2)
C3—C4—C5	122.9 (2)	C12—C13—H13A	119.2
C3—C4—N1	118.2 (2)	C8—C13—H13A	119.2
C5—C4—N1	119.0 (2)	O3—C14—N3	123.0 (2)
C6—C5—C4	118.2 (2)	O3—C14—C15	122.0 (2)
C6—C5—H5A	120.9	N3—C14—C15	115.0 (2)
C4—C5—H5A	120.9	C14—C15—H15A	109.5
C5—C6—C1	120.4 (2)	C14—C15—H15B	109.5
C5—C6—H6A	119.8	H15A—C15—H15B	109.5
C1—C6—H6A	119.8	C14—C15—H15C	109.5
N2—C7—C1	123.7 (2)	H15A—C15—H15C	109.5
N2—C7—H7A	118.2	H15B—C15—H15C	109.5
C1—C7—H7A	118.2
C6—C1—C2—C3	0.9 (4)	C7—N2—C8—C13	−151.3 (2)
C7—C1—C2—C3	−179.8 (2)	C7—N2—C8—C9	30.1 (3)
C1—C2—C3—C4	−1.6 (4)	C13—C8—C9—C10	2.4 (3)
C2—C3—C4—C5	0.9 (4)	N2—C8—C9—C10	−179.1 (2)
C2—C3—C4—N1	−178.2 (2)	C8—C9—C10—C11	−0.4 (4)
O2—N1—C4—C3	13.6 (3)	C9—C10—C11—C12	−1.4 (3)
O1—N1—C4—C3	−166.4 (2)	C9—C10—C11—N3	177.6 (2)
O2—N1—C4—C5	−165.5 (2)	C14—N3—C11—C10	169.9 (2)
O1—N1—C4—C5	14.5 (3)	C14—N3—C11—C12	−11.1 (4)
C3—C4—C5—C6	0.6 (4)	C10—C11—C12—C13	1.2 (3)
N1—C4—C5—C6	179.6 (2)	N3—C11—C12—C13	−177.8 (2)
C4—C5—C6—C1	−1.3 (3)	C11—C12—C13—C8	0.8 (4)
C2—C1—C6—C5	0.6 (3)	C9—C8—C13—C12	−2.6 (4)
C7—C1—C6—C5	−178.7 (2)	N2—C8—C13—C12	178.8 (2)
C8—N2—C7—C1	−179.7 (2)	C11—N3—C14—O3	−4.0 (4)
C2—C1—C7—N2	177.3 (2)	C11—N3—C14—C15	176.0 (2)
C6—C1—C7—N2	−3.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1^i	0.88	2.43	3.263 (3)	157

Symmetry code: (i) x, −y+1/2, z−1/2.