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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048173/wn2091sup1.cif
Contains datablocks zba2, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048173/wn2091Isup2.hkl
Contains datablock I

CCDC reference: 630506

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

Computing details top

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 top
Crystal data top
C15H13N3O3Dx = 1.439 Mg m3
Mr = 283.28Melting point: 497 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71070 Å
a = 7.0477 (8) ÅCell parameters from 7894 reflections
b = 15.1868 (17) Åθ = 3.0–25.4°
c = 24.426 (3) ŵ = 0.10 mm1
V = 2614.4 (5) Å3T = 153 K
Z = 8Block, yellow
F(000) = 11840.38 × 0.28 × 0.20 mm
Data collection top
Rigaku Mercury CCD
diffractometer
2392 independent reflections
Radiation source: fine-focus sealed tube2200 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 88
Tmin = 0.962, Tmax = 0.980k = 1818
23604 measured reflectionsl = 2925
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0512P)2 + 2.827P]
where P = (Fo2 + 2Fc2)/3
2392 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
O10.3086 (3)0.07263 (12)0.67188 (7)0.0363 (5)
O20.3856 (3)0.03098 (12)0.61546 (8)0.0385 (5)
O30.4621 (3)0.71569 (11)0.29691 (7)0.0348 (5)
N10.3465 (3)0.04611 (14)0.62565 (8)0.0285 (5)
N20.3429 (3)0.37099 (13)0.45248 (8)0.0242 (5)
N30.3848 (3)0.58092 (12)0.26271 (8)0.0237 (5)
H3B0.35950.55290.23200.028*
C10.3482 (3)0.22741 (15)0.49499 (9)0.0224 (5)
C20.3512 (3)0.13726 (15)0.48497 (10)0.0253 (5)
H2A0.35610.11650.44830.030*
C30.3471 (3)0.07745 (15)0.52765 (10)0.0260 (5)
H3A0.34590.01590.52080.031*
C40.3449 (3)0.10956 (15)0.58038 (9)0.0227 (5)
C50.3440 (3)0.19894 (16)0.59231 (9)0.0243 (5)
H5A0.34360.21910.62910.029*
C60.3438 (3)0.25790 (16)0.54911 (9)0.0245 (5)
H6A0.34060.31940.55620.029*
C70.3521 (3)0.28737 (16)0.44817 (9)0.0247 (5)
H7A0.36190.26270.41250.030*
C80.3469 (3)0.42199 (15)0.40380 (9)0.0220 (5)
C90.2770 (3)0.39398 (15)0.35312 (9)0.0234 (5)
H9A0.22050.33740.35000.028*
C100.2892 (3)0.44732 (15)0.30780 (9)0.0235 (5)
H10A0.24170.42700.27370.028*
C110.3703 (3)0.53090 (15)0.31132 (9)0.0214 (5)
C120.4357 (3)0.56071 (15)0.36204 (9)0.0247 (5)
H12A0.48920.61790.36540.030*
C130.4221 (3)0.50630 (15)0.40751 (9)0.0244 (5)
H13A0.46530.52720.44200.029*
C140.4334 (3)0.66774 (15)0.25763 (10)0.0243 (5)
C150.4494 (4)0.70047 (17)0.19978 (10)0.0312 (6)
H15A0.48580.76270.20000.047*
H15B0.32680.69380.18130.047*
H15C0.54590.66620.18030.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0448 (11)0.0451 (11)0.0189 (9)0.0038 (9)0.0022 (8)0.0053 (8)
O20.0442 (11)0.0277 (10)0.0435 (11)0.0062 (9)0.0038 (9)0.0108 (8)
O30.0503 (12)0.0246 (9)0.0294 (10)0.0047 (8)0.0047 (8)0.0007 (8)
N10.0248 (11)0.0327 (12)0.0279 (12)0.0024 (9)0.0016 (9)0.0078 (9)
N20.0265 (10)0.0254 (11)0.0207 (10)0.0001 (8)0.0007 (8)0.0021 (8)
N30.0301 (11)0.0224 (10)0.0187 (10)0.0020 (8)0.0001 (8)0.0011 (8)
C10.0200 (11)0.0252 (12)0.0218 (12)0.0006 (9)0.0001 (9)0.0004 (10)
C20.0288 (12)0.0272 (12)0.0199 (11)0.0004 (10)0.0006 (10)0.0025 (10)
C30.0300 (13)0.0211 (12)0.0268 (13)0.0002 (10)0.0019 (10)0.0008 (10)
C40.0218 (11)0.0250 (12)0.0211 (12)0.0002 (10)0.0002 (9)0.0042 (10)
C50.0260 (12)0.0295 (13)0.0175 (11)0.0007 (10)0.0001 (9)0.0021 (10)
C60.0254 (12)0.0225 (12)0.0254 (12)0.0002 (10)0.0005 (10)0.0022 (10)
C70.0256 (12)0.0287 (13)0.0196 (11)0.0013 (10)0.0018 (10)0.0010 (10)
C80.0229 (12)0.0222 (12)0.0209 (12)0.0037 (10)0.0011 (9)0.0003 (9)
C90.0254 (12)0.0201 (11)0.0247 (12)0.0013 (10)0.0017 (10)0.0002 (10)
C100.0268 (12)0.0238 (12)0.0199 (12)0.0019 (10)0.0007 (10)0.0032 (9)
C110.0228 (11)0.0221 (11)0.0193 (11)0.0024 (9)0.0011 (9)0.0005 (9)
C120.0294 (13)0.0210 (11)0.0238 (12)0.0015 (10)0.0025 (10)0.0018 (9)
C130.0294 (12)0.0241 (12)0.0198 (11)0.0018 (10)0.0013 (10)0.0026 (9)
C140.0245 (12)0.0231 (11)0.0251 (13)0.0008 (10)0.0026 (10)0.0021 (10)
C150.0367 (14)0.0283 (13)0.0285 (13)0.0014 (11)0.0019 (11)0.0065 (11)
Geometric parameters (Å, º) top
O1—N11.228 (3)C5—H5A0.9500
O2—N11.228 (3)C6—H6A0.9500
O3—C141.221 (3)C7—H7A0.9500
N1—C41.467 (3)C8—C131.389 (3)
N2—C71.276 (3)C8—C91.399 (3)
N2—C81.419 (3)C9—C101.374 (3)
N3—C141.368 (3)C9—H9A0.9500
N3—C111.413 (3)C10—C111.395 (3)
N3—H3B0.8800C10—H10A0.9500
C1—C21.391 (3)C11—C121.397 (3)
C1—C61.401 (3)C12—C131.388 (3)
C1—C71.462 (3)C12—H12A0.9500
C2—C31.383 (3)C13—H13A0.9500
C2—H2A0.9500C14—C151.502 (3)
C3—C41.377 (3)C15—H15A0.9800
C3—H3A0.9500C15—H15B0.9800
C4—C51.388 (3)C15—H15C0.9800
C5—C61.384 (3)
O2—N1—O1123.2 (2)C13—C8—C9118.2 (2)
O2—N1—C4118.4 (2)C13—C8—N2117.1 (2)
O1—N1—C4118.4 (2)C9—C8—N2124.6 (2)
C7—N2—C8118.2 (2)C10—C9—C8120.8 (2)
C14—N3—C11127.77 (19)C10—C9—H9A119.6
C14—N3—H3B116.1C8—C9—H9A119.6
C11—N3—H3B116.1C9—C10—C11120.8 (2)
C2—C1—C6119.4 (2)C9—C10—H10A119.6
C2—C1—C7118.4 (2)C11—C10—H10A119.6
C6—C1—C7122.2 (2)C10—C11—C12119.0 (2)
C3—C2—C1120.9 (2)C10—C11—N3117.9 (2)
C3—C2—H2A119.5C12—C11—N3123.2 (2)
C1—C2—H2A119.5C13—C12—C11119.6 (2)
C4—C3—C2118.2 (2)C13—C12—H12A120.2
C4—C3—H3A120.9C11—C12—H12A120.2
C2—C3—H3A120.9C12—C13—C8121.5 (2)
C3—C4—C5122.9 (2)C12—C13—H13A119.2
C3—C4—N1118.2 (2)C8—C13—H13A119.2
C5—C4—N1119.0 (2)O3—C14—N3123.0 (2)
C6—C5—C4118.2 (2)O3—C14—C15122.0 (2)
C6—C5—H5A120.9N3—C14—C15115.0 (2)
C4—C5—H5A120.9C14—C15—H15A109.5
C5—C6—C1120.4 (2)C14—C15—H15B109.5
C5—C6—H6A119.8H15A—C15—H15B109.5
C1—C6—H6A119.8C14—C15—H15C109.5
N2—C7—C1123.7 (2)H15A—C15—H15C109.5
N2—C7—H7A118.2H15B—C15—H15C109.5
C1—C7—H7A118.2
C6—C1—C2—C30.9 (4)C7—N2—C8—C13151.3 (2)
C7—C1—C2—C3179.8 (2)C7—N2—C8—C930.1 (3)
C1—C2—C3—C41.6 (4)C13—C8—C9—C102.4 (3)
C2—C3—C4—C50.9 (4)N2—C8—C9—C10179.1 (2)
C2—C3—C4—N1178.2 (2)C8—C9—C10—C110.4 (4)
O2—N1—C4—C313.6 (3)C9—C10—C11—C121.4 (3)
O1—N1—C4—C3166.4 (2)C9—C10—C11—N3177.6 (2)
O2—N1—C4—C5165.5 (2)C14—N3—C11—C10169.9 (2)
O1—N1—C4—C514.5 (3)C14—N3—C11—C1211.1 (4)
C3—C4—C5—C60.6 (4)C10—C11—C12—C131.2 (3)
N1—C4—C5—C6179.6 (2)N3—C11—C12—C13177.8 (2)
C4—C5—C6—C11.3 (3)C11—C12—C13—C80.8 (4)
C2—C1—C6—C50.6 (3)C9—C8—C13—C122.6 (4)
C7—C1—C6—C5178.7 (2)N2—C8—C13—C12178.8 (2)
C8—N2—C7—C1179.7 (2)C11—N3—C14—O34.0 (4)
C2—C1—C7—N2177.3 (2)C11—N3—C14—C15176.0 (2)
C6—C1—C7—N23.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O1i0.882.433.263 (3)157
Symmetry code: (i) x, y+1/2, z1/2.
 

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