In the title compound, C
16H
12N
2O
2, the dihedral angle between the two benzene rings is 85.53 (5)°. The crystal structure is stabilized by intermolecular C—H
O hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 253023
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.117
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C4 .. 5.38 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.44 su
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C4 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.43 Ang.
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C16
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16C .. CG2 .. 2.99 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 33
C5 -C4 -C1 -N1 27.00 14.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 34
C3 -C4 -C1 -N1 -152.00 14.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 35
C8 -C3 -C2 -N2 179.00100.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 36
C4 -C3 -C2 -N2 -1.00 10.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
Crystal data top
C16H12N2O2 | F(000) = 1104 |
Mr = 264.28 | Dx = 1.277 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 18160 reflections |
a = 8.2319 (5) Å | θ = 1.4–27.2° |
b = 22.7570 (15) Å | µ = 0.09 mm−1 |
c = 14.6764 (8) Å | T = 293 K |
V = 2749.4 (3) Å3 | Plate, colorless |
Z = 8 | 0.80 × 0.48 × 0.12 mm |
Data collection top
Stoe IPDS-II diffractometer | 2697 independent reflections |
Radiation source: fine-focus sealed tube | 1818 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.110 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −28→28 |
Tmin = 0.943, Tmax = 0.990 | l = −16→18 |
18348 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0722P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.003 |
2697 reflections | Δρmax = 0.18 e Å−3 |
182 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0125 (12) |
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 | |
C11 | −0.1308 (2) | 0.24270 (7) | 0.17069 (13) | 0.0687 (5) | |
H11 | −0.1746 | 0.2179 | 0.1267 | 0.082* | |
C10 | −0.0423 (2) | 0.29134 (7) | 0.14412 (13) | 0.0681 (5) | |
H10 | −0.0240 | 0.2987 | 0.0826 | 0.082* | |
C16 | −0.2426 (2) | 0.17525 (7) | 0.28957 (16) | 0.0803 (6) | |
H16A | −0.2488 | 0.1736 | 0.3548 | 0.121* | |
H16B | −0.1844 | 0.1416 | 0.2674 | 0.121* | |
H16C | −0.3503 | 0.1754 | 0.2645 | 0.121* | |
C12 | −0.15481 (18) | 0.23066 (6) | 0.26119 (13) | 0.0603 (4) | |
C9 | 0.01844 (17) | 0.32862 (6) | 0.20885 (12) | 0.0554 (4) | |
O1 | 0.12490 (12) | 0.37367 (4) | 0.18365 (9) | 0.0644 (3) | |
C13 | −0.09449 (19) | 0.26892 (7) | 0.32545 (12) | 0.0622 (4) | |
H13 | −0.1115 | 0.2612 | 0.3869 | 0.075* | |
C6 | 0.18283 (17) | 0.46790 (6) | 0.13533 (11) | 0.0528 (4) | |
H6 | 0.2921 | 0.4576 | 0.1366 | 0.063* | |
C14 | −0.00864 (18) | 0.31886 (6) | 0.30008 (12) | 0.0567 (4) | |
C7 | 0.06508 (17) | 0.42713 (6) | 0.15951 (10) | 0.0493 (3) | |
C5 | 0.13720 (18) | 0.52356 (6) | 0.10950 (11) | 0.0537 (4) | |
H5 | 0.2160 | 0.5510 | 0.0936 | 0.064* | |
C8 | −0.09738 (17) | 0.44113 (6) | 0.15837 (10) | 0.0516 (4) | |
H8 | −0.1753 | 0.4136 | 0.1750 | 0.062* | |
O2 | 0.05324 (16) | 0.35989 (6) | 0.35821 (9) | 0.0788 (4) | |
C4 | −0.02505 (18) | 0.53895 (6) | 0.10709 (10) | 0.0497 (4) | |
C3 | −0.14265 (17) | 0.49746 (6) | 0.13171 (10) | 0.0501 (4) | |
C1 | −0.0726 (2) | 0.59665 (7) | 0.07771 (11) | 0.0573 (4) | |
C15 | 0.0322 (4) | 0.35043 (13) | 0.45241 (17) | 0.1157 (9) | |
H15A | 0.0810 | 0.3822 | 0.4857 | 0.174* | |
H15B | 0.0831 | 0.3141 | 0.4694 | 0.174* | |
H15C | −0.0816 | 0.3486 | 0.4662 | 0.174* | |
C2 | −0.3110 (2) | 0.51361 (7) | 0.12917 (13) | 0.0649 (5) | |
N1 | −0.1087 (2) | 0.64250 (6) | 0.05374 (11) | 0.0780 (5) | |
N2 | −0.44391 (19) | 0.52754 (8) | 0.12662 (16) | 0.0973 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0762 (11) | 0.0536 (9) | 0.0763 (12) | −0.0075 (8) | −0.0057 (9) | −0.0001 (8) |
C10 | 0.0746 (11) | 0.0633 (10) | 0.0666 (11) | −0.0055 (8) | −0.0023 (9) | 0.0084 (8) |
C16 | 0.0733 (11) | 0.0527 (10) | 0.1150 (16) | −0.0067 (8) | −0.0017 (11) | 0.0199 (10) |
C12 | 0.0524 (8) | 0.0447 (8) | 0.0839 (12) | 0.0022 (6) | −0.0025 (8) | 0.0100 (8) |
C9 | 0.0481 (8) | 0.0446 (8) | 0.0734 (11) | −0.0003 (6) | 0.0015 (7) | 0.0101 (7) |
O1 | 0.0520 (6) | 0.0504 (6) | 0.0909 (9) | −0.0018 (4) | 0.0025 (5) | 0.0164 (6) |
C13 | 0.0595 (9) | 0.0569 (9) | 0.0702 (11) | −0.0001 (7) | 0.0019 (8) | 0.0116 (8) |
C6 | 0.0455 (7) | 0.0526 (8) | 0.0602 (9) | −0.0048 (6) | 0.0026 (6) | −0.0015 (7) |
C14 | 0.0510 (8) | 0.0497 (8) | 0.0694 (10) | −0.0006 (6) | −0.0009 (7) | 0.0023 (7) |
C7 | 0.0502 (7) | 0.0453 (7) | 0.0524 (8) | −0.0036 (6) | −0.0001 (6) | 0.0026 (6) |
C5 | 0.0543 (8) | 0.0480 (8) | 0.0588 (9) | −0.0120 (6) | 0.0065 (7) | −0.0008 (6) |
C8 | 0.0506 (8) | 0.0462 (7) | 0.0580 (9) | −0.0088 (6) | 0.0026 (6) | 0.0041 (6) |
O2 | 0.0841 (8) | 0.0753 (8) | 0.0769 (9) | −0.0205 (6) | 0.0017 (7) | −0.0106 (6) |
C4 | 0.0578 (8) | 0.0425 (7) | 0.0489 (8) | −0.0056 (6) | 0.0030 (6) | −0.0012 (6) |
C3 | 0.0490 (8) | 0.0495 (8) | 0.0517 (8) | −0.0032 (6) | 0.0003 (6) | 0.0002 (6) |
C1 | 0.0663 (9) | 0.0492 (8) | 0.0564 (9) | −0.0037 (7) | 0.0050 (7) | −0.0015 (7) |
C15 | 0.142 (2) | 0.132 (2) | 0.0729 (14) | −0.0373 (17) | 0.0049 (14) | −0.0211 (14) |
C2 | 0.0554 (9) | 0.0573 (9) | 0.0820 (12) | −0.0045 (7) | 0.0021 (8) | 0.0127 (8) |
N1 | 0.0998 (12) | 0.0535 (8) | 0.0808 (11) | 0.0061 (8) | 0.0068 (9) | 0.0073 (7) |
N2 | 0.0537 (9) | 0.0884 (11) | 0.1499 (19) | 0.0018 (8) | 0.0008 (9) | 0.0303 (11) |
Geometric parameters (Å, º) top
C11—C12 | 1.370 (2) | C6—H6 | 0.9300 |
C11—C10 | 1.382 (2) | C14—O2 | 1.3636 (19) |
C11—H11 | 0.9300 | C7—C8 | 1.375 (2) |
C10—C9 | 1.368 (2) | C5—C4 | 1.381 (2) |
C10—H10 | 0.9300 | C5—H5 | 0.9300 |
C16—C12 | 1.512 (2) | C8—C3 | 1.3911 (19) |
C16—H16A | 0.9600 | C8—H8 | 0.9300 |
C16—H16B | 0.9600 | O2—C15 | 1.410 (3) |
C16—H16C | 0.9600 | C4—C3 | 1.3997 (19) |
C12—C13 | 1.376 (2) | C4—C1 | 1.437 (2) |
C9—C14 | 1.375 (2) | C3—C2 | 1.434 (2) |
C9—O1 | 1.3985 (17) | C1—N1 | 1.140 (2) |
O1—C7 | 1.3595 (17) | C15—H15A | 0.9600 |
C13—C14 | 1.389 (2) | C15—H15B | 0.9600 |
C13—H13 | 0.9300 | C15—H15C | 0.9600 |
C6—C5 | 1.374 (2) | C2—N2 | 1.140 (2) |
C6—C7 | 1.388 (2) | | |
| | | |
C12—C11—C10 | 120.64 (17) | O2—C14—C13 | 125.64 (16) |
C12—C11—H11 | 119.7 | C9—C14—C13 | 118.40 (15) |
C10—C11—H11 | 119.7 | O1—C7—C8 | 124.26 (12) |
C9—C10—C11 | 119.57 (17) | O1—C7—C6 | 114.32 (13) |
C9—C10—H10 | 120.2 | C8—C7—C6 | 121.42 (13) |
C11—C10—H10 | 120.2 | C6—C5—C4 | 120.33 (13) |
C12—C16—H16A | 109.5 | C6—C5—H5 | 119.8 |
C12—C16—H16B | 109.5 | C4—C5—H5 | 119.8 |
H16A—C16—H16B | 109.5 | C7—C8—C3 | 118.52 (13) |
C12—C16—H16C | 109.5 | C7—C8—H8 | 120.7 |
H16A—C16—H16C | 109.5 | C3—C8—H8 | 120.7 |
H16B—C16—H16C | 109.5 | C14—O2—C15 | 117.58 (15) |
C11—C12—C13 | 119.06 (15) | C5—C4—C3 | 119.42 (13) |
C11—C12—C16 | 120.17 (17) | C5—C4—C1 | 120.21 (13) |
C13—C12—C16 | 120.75 (17) | C3—C4—C1 | 120.36 (13) |
C10—C9—C14 | 121.11 (14) | C8—C3—C4 | 120.59 (13) |
C10—C9—O1 | 119.99 (15) | C8—C3—C2 | 120.15 (13) |
C14—C9—O1 | 118.51 (14) | C4—C3—C2 | 119.26 (13) |
C7—O1—C9 | 119.87 (11) | N1—C1—C4 | 179.13 (19) |
C12—C13—C14 | 121.16 (17) | O2—C15—H15A | 109.5 |
C12—C13—H13 | 119.4 | O2—C15—H15B | 109.5 |
C14—C13—H13 | 119.4 | H15A—C15—H15B | 109.5 |
C5—C6—C7 | 119.71 (14) | O2—C15—H15C | 109.5 |
C5—C6—H6 | 120.1 | H15A—C15—H15C | 109.5 |
C7—C6—H6 | 120.1 | H15B—C15—H15C | 109.5 |
O2—C14—C9 | 115.97 (14) | N2—C2—C3 | 178.62 (18) |
| | | |
C12—C11—C10—C9 | −1.7 (3) | C5—C6—C7—C8 | −0.1 (2) |
C10—C11—C12—C13 | 2.4 (3) | C7—C6—C5—C4 | −0.3 (2) |
C10—C11—C12—C16 | −176.04 (16) | O1—C7—C8—C3 | −179.60 (14) |
C11—C10—C9—C14 | −0.7 (2) | C6—C7—C8—C3 | 0.4 (2) |
C11—C10—C9—O1 | 172.00 (15) | C9—C14—O2—C15 | −178.08 (19) |
C10—C9—O1—C7 | 89.45 (18) | C13—C14—O2—C15 | 1.6 (3) |
C14—C9—O1—C7 | −97.67 (17) | C6—C5—C4—C3 | 0.4 (2) |
C11—C12—C13—C14 | −0.8 (2) | C6—C5—C4—C1 | −178.31 (15) |
C16—C12—C13—C14 | 177.68 (15) | C7—C8—C3—C4 | −0.3 (2) |
C10—C9—C14—O2 | −177.98 (14) | C7—C8—C3—C2 | 179.67 (15) |
O1—C9—C14—O2 | 9.2 (2) | C5—C4—C3—C8 | 0.0 (2) |
C10—C9—C14—C13 | 2.3 (2) | C1—C4—C3—C8 | 178.64 (14) |
O1—C9—C14—C13 | −170.52 (13) | C5—C4—C3—C2 | 179.96 (15) |
C12—C13—C14—O2 | 178.73 (15) | C1—C4—C3—C2 | −1.4 (2) |
C12—C13—C14—C9 | −1.6 (2) | C5—C4—C1—N1 | 27 (14) |
C9—O1—C7—C8 | 0.4 (2) | C3—C4—C1—N1 | −152 (14) |
C9—O1—C7—C6 | −179.54 (14) | C8—C3—C2—N2 | 179 (100) |
C5—C6—C7—O1 | 179.93 (14) | C4—C3—C2—N2 | −1 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.59 | 3.4276 (18) | 150 |
C16—H16C···Cg2i | 0.96 | 2.99 | 3.6114 (18) | 124 |
Symmetry code: (i) x−1/2, y, −z+1/2. |