The title compound, C
13H
11N
3O, 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
CCDC reference: 277804
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
C13H11N3O | F(000) = 472 |
Mr = 225.25 | Dx = 1.287 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1750 reflections |
a = 4.9916 (9) Å | θ = 3.3–25.3° |
b = 6.2388 (11) Å | µ = 0.09 mm−1 |
c = 37.342 (7) Å | T = 294 K |
V = 1162.9 (4) Å3 | Block, brown |
Z = 4 | 0.26 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 1445 independent reflections |
Radiation source: fine-focus sealed tube | 1016 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 26.4°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→4 |
Tmin = 0.970, Tmax = 0.990 | k = −7→7 |
6580 measured reflections | l = −42→46 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.08 | Δρmax = 0.14 e Å−3 |
1445 reflections | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.4331 (5) | −0.1219 (4) | 0.15157 (6) | 0.0504 (6) | |
H1A | 0.483 (6) | −0.243 (5) | 0.1634 (7) | 0.071 (10)* | |
N2 | 0.5754 (4) | −0.0614 (3) | 0.12285 (5) | 0.0477 (5) | |
N3 | 0.7448 (5) | −0.2042 (3) | 0.11450 (5) | 0.0522 (6) | |
O1 | −0.4419 (4) | 0.5608 (3) | 0.20709 (5) | 0.0631 (6) | |
C1 | −0.3657 (5) | 0.3827 (4) | 0.21543 (7) | 0.0498 (7) | |
H1 | −0.4499 | 0.3190 | 0.2349 | 0.060* | |
C2 | −0.1569 (5) | 0.2597 (4) | 0.19804 (6) | 0.0427 (6) | |
C3 | −0.0935 (5) | 0.0591 (4) | 0.21176 (6) | 0.0483 (6) | |
H3 | −0.1842 | 0.0082 | 0.2318 | 0.058* | |
C4 | 0.1018 (5) | −0.0653 (4) | 0.19612 (7) | 0.0488 (6) | |
H4 | 0.1419 | −0.1993 | 0.2056 | 0.059* | |
C5 | 0.2389 (5) | 0.0086 (4) | 0.16627 (6) | 0.0411 (6) | |
C6 | 0.1773 (5) | 0.2100 (4) | 0.15229 (6) | 0.0467 (6) | |
H6 | 0.2695 | 0.2617 | 0.1324 | 0.056* | |
C7 | −0.0203 (5) | 0.3323 (4) | 0.16797 (6) | 0.0480 (7) | |
H7 | −0.0629 | 0.4654 | 0.1583 | 0.058* | |
C8 | 0.9059 (5) | −0.1477 (4) | 0.08453 (6) | 0.0510 (7) | |
C9 | 0.9038 (7) | 0.0481 (5) | 0.06745 (8) | 0.0680 (8) | |
H9 | 0.7881 | 0.1560 | 0.0749 | 0.082* | |
C10 | 1.0775 (8) | 0.0821 (6) | 0.03877 (9) | 0.0848 (10) | |
H10 | 1.0768 | 0.2134 | 0.0270 | 0.102* | |
C11 | 1.2498 (7) | −0.0767 (7) | 0.02782 (8) | 0.0823 (11) | |
H11 | 1.3644 | −0.0531 | 0.0086 | 0.099* | |
C12 | 1.2527 (7) | −0.2687 (6) | 0.04513 (8) | 0.0770 (10) | |
H12 | 1.3709 | −0.3756 | 0.0379 | 0.092* | |
C13 | 1.0804 (6) | −0.3048 (5) | 0.07336 (7) | 0.0640 (8) | |
H13 | 1.0822 | −0.4366 | 0.0850 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0503 (13) | 0.0507 (14) | 0.0504 (13) | 0.0110 (13) | 0.0068 (11) | 0.0015 (11) |
N2 | 0.0432 (12) | 0.0560 (13) | 0.0438 (12) | 0.0023 (13) | −0.0003 (10) | −0.0042 (10) |
N3 | 0.0490 (12) | 0.0579 (13) | 0.0495 (12) | 0.0134 (13) | 0.0058 (11) | −0.0084 (11) |
O1 | 0.0717 (13) | 0.0518 (11) | 0.0660 (12) | 0.0245 (12) | 0.0073 (11) | 0.0036 (9) |
C1 | 0.0494 (16) | 0.0523 (16) | 0.0478 (15) | 0.0075 (14) | 0.0049 (12) | −0.0016 (12) |
C2 | 0.0413 (14) | 0.0405 (14) | 0.0465 (14) | 0.0070 (12) | 0.0016 (11) | −0.0017 (11) |
C3 | 0.0485 (15) | 0.0480 (15) | 0.0483 (14) | 0.0024 (14) | 0.0091 (13) | 0.0035 (12) |
C4 | 0.0511 (15) | 0.0423 (13) | 0.0530 (15) | 0.0110 (14) | 0.0045 (14) | 0.0052 (12) |
C5 | 0.0374 (12) | 0.0421 (14) | 0.0438 (14) | 0.0070 (12) | −0.0021 (11) | −0.0066 (11) |
C6 | 0.0480 (16) | 0.0502 (15) | 0.0421 (13) | 0.0063 (14) | 0.0023 (12) | 0.0039 (12) |
C7 | 0.0521 (16) | 0.0419 (14) | 0.0501 (15) | 0.0074 (13) | −0.0006 (13) | 0.0042 (11) |
C8 | 0.0468 (15) | 0.0645 (17) | 0.0416 (14) | 0.0011 (16) | 0.0020 (13) | −0.0092 (12) |
C9 | 0.0653 (19) | 0.075 (2) | 0.0632 (19) | 0.002 (2) | 0.0096 (17) | 0.0016 (17) |
C10 | 0.091 (2) | 0.095 (2) | 0.069 (2) | −0.011 (3) | 0.011 (2) | 0.0087 (19) |
C11 | 0.068 (2) | 0.121 (3) | 0.058 (2) | −0.015 (3) | 0.0158 (18) | −0.012 (2) |
C12 | 0.0620 (19) | 0.105 (3) | 0.064 (2) | 0.003 (2) | 0.0127 (18) | −0.025 (2) |
C13 | 0.0548 (17) | 0.0779 (19) | 0.0593 (17) | 0.0097 (19) | 0.0065 (15) | −0.0143 (15) |
Geometric parameters (Å, º) top
N1—N2 | 1.341 (3) | C6—C7 | 1.378 (3) |
N1—C5 | 1.380 (3) | C6—H6 | 0.9300 |
N1—H1A | 0.91 (3) | C7—H7 | 0.9300 |
N2—N3 | 1.267 (3) | C8—C13 | 1.376 (4) |
N3—C8 | 1.422 (3) | C8—C9 | 1.378 (4) |
O1—C1 | 1.215 (3) | C9—C10 | 1.394 (4) |
C1—C2 | 1.448 (3) | C9—H9 | 0.9300 |
C1—H1 | 0.9300 | C10—C11 | 1.375 (5) |
C2—C3 | 1.389 (3) | C10—H10 | 0.9300 |
C2—C7 | 1.390 (3) | C11—C12 | 1.361 (5) |
C3—C4 | 1.376 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.379 (4) |
C4—C5 | 1.387 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.395 (3) | | |
| | | |
N2—N1—C5 | 121.6 (2) | C5—C6—H6 | 120.1 |
N2—N1—H1A | 118.4 (18) | C6—C7—C2 | 120.9 (2) |
C5—N1—H1A | 119.4 (17) | C6—C7—H7 | 119.5 |
N3—N2—N1 | 110.6 (2) | C2—C7—H7 | 119.5 |
N2—N3—C8 | 113.4 (2) | C13—C8—C9 | 119.7 (3) |
O1—C1—C2 | 126.5 (2) | C13—C8—N3 | 114.8 (2) |
O1—C1—H1 | 116.7 | C9—C8—N3 | 125.4 (3) |
C2—C1—H1 | 116.7 | C8—C9—C10 | 119.1 (3) |
C3—C2—C7 | 118.7 (2) | C8—C9—H9 | 120.5 |
C3—C2—C1 | 118.4 (2) | C10—C9—H9 | 120.5 |
C7—C2—C1 | 122.9 (2) | C11—C10—C9 | 120.5 (3) |
C4—C3—C2 | 120.9 (2) | C11—C10—H10 | 119.7 |
C4—C3—H3 | 119.6 | C9—C10—H10 | 119.7 |
C2—C3—H3 | 119.6 | C12—C11—C10 | 120.0 (3) |
C3—C4—C5 | 120.2 (2) | C12—C11—H11 | 120.0 |
C3—C4—H4 | 119.9 | C10—C11—H11 | 120.0 |
C5—C4—H4 | 119.9 | C11—C12—C13 | 120.0 (3) |
N1—C5—C4 | 118.0 (2) | C11—C12—H12 | 120.0 |
N1—C5—C6 | 122.5 (2) | C13—C12—H12 | 120.0 |
C4—C5—C6 | 119.4 (2) | C8—C13—C12 | 120.7 (3) |
C7—C6—C5 | 119.8 (2) | C8—C13—H13 | 119.7 |
C7—C6—H6 | 120.1 | C12—C13—H13 | 119.7 |
| | | |
C5—N1—N2—N3 | 178.8 (2) | C5—C6—C7—C2 | 1.2 (3) |
N1—N2—N3—C8 | −178.9 (2) | C3—C2—C7—C6 | −1.0 (4) |
O1—C1—C2—C3 | 178.9 (3) | C1—C2—C7—C6 | 179.9 (2) |
O1—C1—C2—C7 | −2.0 (4) | N2—N3—C8—C13 | −176.1 (2) |
C7—C2—C3—C4 | 0.4 (4) | N2—N3—C8—C9 | 5.9 (4) |
C1—C2—C3—C4 | 179.5 (2) | C13—C8—C9—C10 | 0.7 (5) |
C2—C3—C4—C5 | 0.1 (4) | N3—C8—C9—C10 | 178.6 (3) |
N2—N1—C5—C4 | −179.6 (2) | C8—C9—C10—C11 | −0.4 (5) |
N2—N1—C5—C6 | 0.3 (4) | C9—C10—C11—C12 | −0.4 (5) |
C3—C4—C5—N1 | 179.9 (2) | C10—C11—C12—C13 | 0.8 (5) |
C3—C4—C5—C6 | 0.1 (4) | C9—C8—C13—C12 | −0.3 (4) |
N1—C5—C6—C7 | 179.4 (2) | N3—C8—C13—C12 | −178.4 (2) |
C4—C5—C6—C7 | −0.7 (3) | C11—C12—C13—C8 | −0.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.91 (3) | 2.07 (3) | 2.934 (3) | 157 (3) |
C4—H4···O1i | 0.93 | 2.56 | 3.286 (3) | 135 |
Symmetry code: (i) x+1, y−1, z. |