The title compound, C
13H
10N
2O
2, is approximately planar in the solid state and displays a
trans configuration with respect to the azo double bond. Molecules form infinite chains linked by O—H
O hydrogen bonds along the
a axis.
Supporting information
CCDC reference: 274637
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.129
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C11 .. 5.28 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 5.84 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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
(
E)-4-[(4-Hydroxyphenyl)diazenyl]benzaldehyde
top
Crystal data top
C13H10N2O2 | F(000) = 472 |
Mr = 226.23 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/c | Melting point = 470–472 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.405 (2) Å | Cell parameters from 1178 reflections |
b = 25.820 (9) Å | θ = 3.2–23.6° |
c = 7.197 (2) Å | µ = 0.10 mm−1 |
β = 114.140 (6)° | T = 293 K |
V = 1086.2 (6) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.14 × 0.08 mm |
Data collection top
Bruker CCD area-detector diffractometer | 2206 independent reflections |
Radiation source: fine-focus sealed tube | 1083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→7 |
Tmin = 0.972, Tmax = 0.991 | k = −32→31 |
6049 measured reflections | l = −8→5 |
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)] = 0.046 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.0666P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.14 e Å−3 |
2206 reflections | Δρmin = −0.18 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 | |
O1 | 0.5417 (3) | 0.24752 (6) | 0.8534 (3) | 0.0704 (6) | |
H1A | 0.678 (5) | 0.2396 (10) | 0.848 (4) | 0.101 (10)* | |
O2 | 0.0528 (3) | 0.72024 (6) | 0.6533 (3) | 0.0746 (6) | |
N1 | 0.3600 (3) | 0.45822 (6) | 0.7602 (3) | 0.0460 (5) | |
N2 | 0.1828 (3) | 0.47258 (7) | 0.7783 (3) | 0.0475 (5) | |
C1 | 0.5030 (4) | 0.29931 (8) | 0.8303 (3) | 0.0499 (6) | |
C2 | 0.3145 (4) | 0.31786 (8) | 0.8571 (4) | 0.0544 (7) | |
H2 | 0.2225 | 0.2951 | 0.8903 | 0.065* | |
C3 | 0.2629 (4) | 0.36972 (9) | 0.8348 (3) | 0.0495 (6) | |
H3 | 0.1348 | 0.3820 | 0.8509 | 0.059* | |
C4 | 0.4028 (4) | 0.40405 (8) | 0.7879 (3) | 0.0411 (5) | |
C5 | 0.5906 (4) | 0.38527 (8) | 0.7629 (3) | 0.0484 (6) | |
H5 | 0.6845 | 0.4080 | 0.7320 | 0.058* | |
C6 | 0.6411 (4) | 0.33311 (8) | 0.7831 (3) | 0.0516 (6) | |
H6 | 0.7679 | 0.3207 | 0.7651 | 0.062* | |
C7 | 0.1358 (3) | 0.52650 (8) | 0.7486 (3) | 0.0402 (5) | |
C8 | −0.0583 (4) | 0.54279 (8) | 0.7695 (3) | 0.0491 (6) | |
H8 | −0.1483 | 0.5190 | 0.8004 | 0.059* | |
C9 | −0.1192 (4) | 0.59427 (8) | 0.7448 (3) | 0.0493 (6) | |
H9 | −0.2512 | 0.6051 | 0.7575 | 0.059* | |
C10 | 0.0151 (4) | 0.63010 (8) | 0.7009 (3) | 0.0433 (6) | |
C11 | −0.0527 (4) | 0.68452 (9) | 0.6803 (4) | 0.0578 (7) | |
H11 | −0.1903 | 0.6923 | 0.6888 | 0.069* | |
C12 | 0.2087 (4) | 0.61333 (8) | 0.6770 (3) | 0.0507 (6) | |
H12 | 0.2983 | 0.6371 | 0.6456 | 0.061* | |
C13 | 0.2686 (4) | 0.56217 (8) | 0.6992 (3) | 0.0485 (6) | |
H13 | 0.3975 | 0.5512 | 0.6815 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0725 (13) | 0.0370 (10) | 0.1168 (17) | −0.0004 (9) | 0.0542 (13) | 0.0006 (9) |
O2 | 0.0663 (12) | 0.0424 (11) | 0.1235 (17) | −0.0034 (9) | 0.0474 (12) | 0.0024 (10) |
N1 | 0.0479 (11) | 0.0421 (12) | 0.0494 (13) | 0.0005 (9) | 0.0212 (10) | −0.0014 (9) |
N2 | 0.0494 (12) | 0.0441 (12) | 0.0515 (12) | −0.0003 (9) | 0.0231 (10) | −0.0022 (9) |
C1 | 0.0544 (15) | 0.0351 (13) | 0.0630 (17) | −0.0048 (11) | 0.0267 (13) | −0.0057 (11) |
C2 | 0.0565 (15) | 0.0417 (15) | 0.0755 (19) | −0.0060 (11) | 0.0377 (14) | 0.0006 (12) |
C3 | 0.0480 (14) | 0.0484 (15) | 0.0574 (16) | −0.0018 (11) | 0.0268 (13) | −0.0049 (12) |
C4 | 0.0465 (14) | 0.0357 (13) | 0.0412 (14) | −0.0021 (10) | 0.0181 (11) | −0.0015 (10) |
C5 | 0.0482 (14) | 0.0431 (14) | 0.0584 (16) | −0.0049 (11) | 0.0264 (13) | −0.0013 (11) |
C6 | 0.0498 (14) | 0.0425 (15) | 0.0698 (17) | −0.0018 (11) | 0.0319 (13) | −0.0040 (12) |
C7 | 0.0428 (13) | 0.0371 (13) | 0.0407 (14) | −0.0002 (10) | 0.0171 (11) | −0.0012 (10) |
C8 | 0.0505 (14) | 0.0471 (15) | 0.0572 (16) | −0.0033 (11) | 0.0298 (13) | 0.0022 (11) |
C9 | 0.0429 (13) | 0.0503 (15) | 0.0608 (17) | 0.0008 (11) | 0.0272 (12) | −0.0028 (12) |
C10 | 0.0417 (13) | 0.0369 (13) | 0.0498 (15) | 0.0031 (10) | 0.0172 (12) | −0.0012 (10) |
C11 | 0.0489 (15) | 0.0517 (16) | 0.076 (2) | 0.0054 (13) | 0.0291 (14) | −0.0023 (13) |
C12 | 0.0465 (14) | 0.0437 (15) | 0.0676 (17) | −0.0016 (11) | 0.0289 (13) | 0.0039 (11) |
C13 | 0.0437 (14) | 0.0421 (14) | 0.0652 (17) | 0.0042 (11) | 0.0279 (13) | 0.0035 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.358 (3) | C5—H5 | 0.9300 |
O1—H1A | 0.91 (3) | C6—H6 | 0.9300 |
O2—C11 | 1.205 (2) | C7—C8 | 1.378 (3) |
N1—N2 | 1.250 (2) | C7—C13 | 1.395 (3) |
N1—C4 | 1.424 (3) | C8—C9 | 1.376 (3) |
N2—C7 | 1.422 (3) | C8—H8 | 0.9300 |
C1—C6 | 1.380 (3) | C9—C10 | 1.384 (3) |
C1—C2 | 1.383 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.373 (3) | C10—C12 | 1.389 (3) |
C2—H2 | 0.9300 | C10—C11 | 1.460 (3) |
C3—C4 | 1.396 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.367 (3) |
C4—C5 | 1.375 (3) | C12—H12 | 0.9300 |
C5—C6 | 1.379 (3) | C13—H13 | 0.9300 |
| | | |
C1—O1—H1A | 110.2 (17) | C8—C7—C13 | 119.9 (2) |
N2—N1—C4 | 114.05 (17) | C8—C7—N2 | 115.31 (18) |
N1—N2—C7 | 114.82 (17) | C13—C7—N2 | 124.84 (18) |
O1—C1—C6 | 123.3 (2) | C9—C8—C7 | 120.1 (2) |
O1—C1—C2 | 116.8 (2) | C9—C8—H8 | 120.0 |
C6—C1—C2 | 119.9 (2) | C7—C8—H8 | 120.0 |
C3—C2—C1 | 120.3 (2) | C8—C9—C10 | 120.4 (2) |
C3—C2—H2 | 119.9 | C8—C9—H9 | 119.8 |
C1—C2—H2 | 119.9 | C10—C9—H9 | 119.8 |
C2—C3—C4 | 120.0 (2) | C9—C10—C12 | 119.3 (2) |
C2—C3—H3 | 120.0 | C9—C10—C11 | 118.6 (2) |
C4—C3—H3 | 120.0 | C12—C10—C11 | 122.1 (2) |
C5—C4—C3 | 119.3 (2) | O2—C11—C10 | 126.1 (2) |
C5—C4—N1 | 117.18 (18) | O2—C11—H11 | 116.9 |
C3—C4—N1 | 123.48 (19) | C10—C11—H11 | 116.9 |
C4—C5—C6 | 120.7 (2) | C13—C12—C10 | 120.6 (2) |
C4—C5—H5 | 119.7 | C13—C12—H12 | 119.7 |
C6—C5—H5 | 119.7 | C10—C12—H12 | 119.7 |
C5—C6—C1 | 119.8 (2) | C12—C13—C7 | 119.8 (2) |
C5—C6—H6 | 120.1 | C12—C13—H13 | 120.1 |
C1—C6—H6 | 120.1 | C7—C13—H13 | 120.1 |
| | | |
C4—N1—N2—C7 | −179.26 (16) | N1—N2—C7—C13 | 1.1 (3) |
O1—C1—C2—C3 | −179.5 (2) | C13—C7—C8—C9 | −1.0 (3) |
C6—C1—C2—C3 | 0.7 (4) | N2—C7—C8—C9 | 179.72 (19) |
C1—C2—C3—C4 | −1.0 (3) | C7—C8—C9—C10 | −0.7 (3) |
C2—C3—C4—C5 | 0.5 (3) | C8—C9—C10—C12 | 1.7 (3) |
C2—C3—C4—N1 | 179.3 (2) | C8—C9—C10—C11 | −178.6 (2) |
N2—N1—C4—C5 | 177.7 (2) | C9—C10—C11—O2 | 175.8 (2) |
N2—N1—C4—C3 | −1.1 (3) | C12—C10—C11—O2 | −4.5 (4) |
C3—C4—C5—C6 | 0.2 (3) | C9—C10—C12—C13 | −0.9 (3) |
N1—C4—C5—C6 | −178.69 (19) | C11—C10—C12—C13 | 179.4 (2) |
C4—C5—C6—C1 | −0.4 (3) | C10—C12—C13—C7 | −0.7 (3) |
O1—C1—C6—C5 | −179.8 (2) | C8—C7—C13—C12 | 1.7 (3) |
C2—C1—C6—C5 | 0.0 (3) | N2—C7—C13—C12 | −179.1 (2) |
N1—N2—C7—C8 | −179.61 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.91 (3) | 1.80 (3) | 2.711 (3) | 176 (3) |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |