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The title compound, C13H11N3O, is essentially planar in the solid state and displays a trans configuration with respect to the azo double bond. The dihedral angle between the planes of the two aromatic rings is 4.9 (4)°. Mol­ecules form infinite chains via N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018751/wn6356sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018751/wn6356Isup2.hkl
Contains datablock I

CCDC reference: 277804

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.094
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - N3 .. 5.88 su
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 26.42 From the CIF: _reflns_number_total 1445 Count of symmetry unique reflns 1453 Completeness (_total/calc) 99.45% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
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 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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

4-(N-Phenylazo)aminobenzaldehyde top
Crystal data top
C13H11N3OF(000) = 472
Mr = 225.25Dx = 1.287 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1750 reflections
a = 4.9916 (9) Åθ = 3.3–25.3°
b = 6.2388 (11) ŵ = 0.09 mm1
c = 37.342 (7) ÅT = 294 K
V = 1162.9 (4) Å3Block, brown
Z = 40.26 × 0.20 × 0.12 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1445 independent reflections
Radiation source: fine-focus sealed tube1016 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 64
Tmin = 0.970, Tmax = 0.990k = 77
6580 measured reflectionsl = 4246
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0383P)2 + 0.132P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.14 e Å3
1445 reflectionsΔρmin = 0.15 e Å3
158 parameters
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
N10.4331 (5)0.1219 (4)0.15157 (6)0.0504 (6)
H1A0.483 (6)0.243 (5)0.1634 (7)0.071 (10)*
N20.5754 (4)0.0614 (3)0.12285 (5)0.0477 (5)
N30.7448 (5)0.2042 (3)0.11450 (5)0.0522 (6)
O10.4419 (4)0.5608 (3)0.20709 (5)0.0631 (6)
C10.3657 (5)0.3827 (4)0.21543 (7)0.0498 (7)
H10.44990.31900.23490.060*
C20.1569 (5)0.2597 (4)0.19804 (6)0.0427 (6)
C30.0935 (5)0.0591 (4)0.21176 (6)0.0483 (6)
H30.18420.00820.23180.058*
C40.1018 (5)0.0653 (4)0.19612 (7)0.0488 (6)
H40.14190.19930.20560.059*
C50.2389 (5)0.0086 (4)0.16627 (6)0.0411 (6)
C60.1773 (5)0.2100 (4)0.15229 (6)0.0467 (6)
H60.26950.26170.13240.056*
C70.0203 (5)0.3323 (4)0.16797 (6)0.0480 (7)
H70.06290.46540.15830.058*
C80.9059 (5)0.1477 (4)0.08453 (6)0.0510 (7)
C90.9038 (7)0.0481 (5)0.06745 (8)0.0680 (8)
H90.78810.15600.07490.082*
C101.0775 (8)0.0821 (6)0.03877 (9)0.0848 (10)
H101.07680.21340.02700.102*
C111.2498 (7)0.0767 (7)0.02782 (8)0.0823 (11)
H111.36440.05310.00860.099*
C121.2527 (7)0.2687 (6)0.04513 (8)0.0770 (10)
H121.37090.37560.03790.092*
C131.0804 (6)0.3048 (5)0.07336 (7)0.0640 (8)
H131.08220.43660.08500.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0503 (13)0.0507 (14)0.0504 (13)0.0110 (13)0.0068 (11)0.0015 (11)
N20.0432 (12)0.0560 (13)0.0438 (12)0.0023 (13)0.0003 (10)0.0042 (10)
N30.0490 (12)0.0579 (13)0.0495 (12)0.0134 (13)0.0058 (11)0.0084 (11)
O10.0717 (13)0.0518 (11)0.0660 (12)0.0245 (12)0.0073 (11)0.0036 (9)
C10.0494 (16)0.0523 (16)0.0478 (15)0.0075 (14)0.0049 (12)0.0016 (12)
C20.0413 (14)0.0405 (14)0.0465 (14)0.0070 (12)0.0016 (11)0.0017 (11)
C30.0485 (15)0.0480 (15)0.0483 (14)0.0024 (14)0.0091 (13)0.0035 (12)
C40.0511 (15)0.0423 (13)0.0530 (15)0.0110 (14)0.0045 (14)0.0052 (12)
C50.0374 (12)0.0421 (14)0.0438 (14)0.0070 (12)0.0021 (11)0.0066 (11)
C60.0480 (16)0.0502 (15)0.0421 (13)0.0063 (14)0.0023 (12)0.0039 (12)
C70.0521 (16)0.0419 (14)0.0501 (15)0.0074 (13)0.0006 (13)0.0042 (11)
C80.0468 (15)0.0645 (17)0.0416 (14)0.0011 (16)0.0020 (13)0.0092 (12)
C90.0653 (19)0.075 (2)0.0632 (19)0.002 (2)0.0096 (17)0.0016 (17)
C100.091 (2)0.095 (2)0.069 (2)0.011 (3)0.011 (2)0.0087 (19)
C110.068 (2)0.121 (3)0.058 (2)0.015 (3)0.0158 (18)0.012 (2)
C120.0620 (19)0.105 (3)0.064 (2)0.003 (2)0.0127 (18)0.025 (2)
C130.0548 (17)0.0779 (19)0.0593 (17)0.0097 (19)0.0065 (15)0.0143 (15)
Geometric parameters (Å, º) top
N1—N21.341 (3)C6—C71.378 (3)
N1—C51.380 (3)C6—H60.9300
N1—H1A0.91 (3)C7—H70.9300
N2—N31.267 (3)C8—C131.376 (4)
N3—C81.422 (3)C8—C91.378 (4)
O1—C11.215 (3)C9—C101.394 (4)
C1—C21.448 (3)C9—H90.9300
C1—H10.9300C10—C111.375 (5)
C2—C31.389 (3)C10—H100.9300
C2—C71.390 (3)C11—C121.361 (5)
C3—C41.376 (3)C11—H110.9300
C3—H30.9300C12—C131.379 (4)
C4—C51.387 (3)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.395 (3)
N2—N1—C5121.6 (2)C5—C6—H6120.1
N2—N1—H1A118.4 (18)C6—C7—C2120.9 (2)
C5—N1—H1A119.4 (17)C6—C7—H7119.5
N3—N2—N1110.6 (2)C2—C7—H7119.5
N2—N3—C8113.4 (2)C13—C8—C9119.7 (3)
O1—C1—C2126.5 (2)C13—C8—N3114.8 (2)
O1—C1—H1116.7C9—C8—N3125.4 (3)
C2—C1—H1116.7C8—C9—C10119.1 (3)
C3—C2—C7118.7 (2)C8—C9—H9120.5
C3—C2—C1118.4 (2)C10—C9—H9120.5
C7—C2—C1122.9 (2)C11—C10—C9120.5 (3)
C4—C3—C2120.9 (2)C11—C10—H10119.7
C4—C3—H3119.6C9—C10—H10119.7
C2—C3—H3119.6C12—C11—C10120.0 (3)
C3—C4—C5120.2 (2)C12—C11—H11120.0
C3—C4—H4119.9C10—C11—H11120.0
C5—C4—H4119.9C11—C12—C13120.0 (3)
N1—C5—C4118.0 (2)C11—C12—H12120.0
N1—C5—C6122.5 (2)C13—C12—H12120.0
C4—C5—C6119.4 (2)C8—C13—C12120.7 (3)
C7—C6—C5119.8 (2)C8—C13—H13119.7
C7—C6—H6120.1C12—C13—H13119.7
C5—N1—N2—N3178.8 (2)C5—C6—C7—C21.2 (3)
N1—N2—N3—C8178.9 (2)C3—C2—C7—C61.0 (4)
O1—C1—C2—C3178.9 (3)C1—C2—C7—C6179.9 (2)
O1—C1—C2—C72.0 (4)N2—N3—C8—C13176.1 (2)
C7—C2—C3—C40.4 (4)N2—N3—C8—C95.9 (4)
C1—C2—C3—C4179.5 (2)C13—C8—C9—C100.7 (5)
C2—C3—C4—C50.1 (4)N3—C8—C9—C10178.6 (3)
N2—N1—C5—C4179.6 (2)C8—C9—C10—C110.4 (5)
N2—N1—C5—C60.3 (4)C9—C10—C11—C120.4 (5)
C3—C4—C5—N1179.9 (2)C10—C11—C12—C130.8 (5)
C3—C4—C5—C60.1 (4)C9—C8—C13—C120.3 (4)
N1—C5—C6—C7179.4 (2)N3—C8—C13—C12178.4 (2)
C4—C5—C6—C70.7 (3)C11—C12—C13—C80.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.91 (3)2.07 (3)2.934 (3)157 (3)
C4—H4···O1i0.932.563.286 (3)135
Symmetry code: (i) x+1, y1, z.
 

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