The title molecule, C
16H
11N
3O, contains a benzene ring fused to an oxazine ring and one phenyl ring bound to the N atom. The two aromatic rings are not coplanar because of steric hindrance, the shortest H
H contact being 2.45 (4) Å. The dihedral angles between these two rings is 52.28 (1)°.
Supporting information
CCDC reference: 236109
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.098
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
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No errors found in this datablock
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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) and PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
2,3-Dihydro-4-phenyl-1,4-benzoxazine-6,7-dicarbonitrile
top
Crystal data top
C16H11N3O | F(000) = 544 |
Mr = 261.28 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8295 reflections |
a = 14.3699 (14) Å | θ = 1.7–28.3° |
b = 7.5806 (4) Å | µ = 0.09 mm−1 |
c = 13.1208 (14) Å | T = 293 K |
β = 114.879 (7)° | Prism, colourless |
V = 1296.6 (2) Å3 | 0.35 × 0.22 × 0.10 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 2264 independent reflections |
Radiation source: fine-focus sealed tube | 1449 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.050 |
ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: integration (X-RED32; Stoe&Cie, 2002) | h = −17→17 |
Tmin = 0.980, Tmax = 0.993 | k = −8→8 |
15978 measured reflections | l = −15→15 |
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)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.025 |
2264 reflections | Δρmax = 0.18 e Å−3 |
226 parameters | Δρmin = −0.16 e Å−3 |
4 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.031 (4) |
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 | 0.65103 (11) | 0.74580 (19) | 0.22598 (13) | 0.0630 (5) | |
N1 | 0.76367 (12) | 0.4286 (2) | 0.27311 (15) | 0.0594 (5) | |
N2 | 0.24652 (15) | 0.4441 (3) | 0.00431 (19) | 0.0806 (7) | |
N3 | 0.38976 (15) | −0.0061 (3) | 0.04340 (17) | 0.0699 (6) | |
C1 | 0.81813 (17) | 0.1991 (3) | 0.1792 (2) | 0.0547 (6) | |
C2 | 0.8885 (2) | 0.0717 (3) | 0.1836 (3) | 0.0680 (7) | |
C3 | 0.9719 (2) | 0.0353 (4) | 0.2825 (3) | 0.0799 (9) | |
C4 | 0.9839 (2) | 0.1242 (4) | 0.3783 (3) | 0.0816 (9) | |
C5 | 0.91337 (17) | 0.2478 (4) | 0.3764 (2) | 0.0698 (7) | |
C6 | 0.83006 (14) | 0.2888 (3) | 0.27597 (18) | 0.0513 (5) | |
C7 | 0.65881 (14) | 0.4266 (3) | 0.21190 (16) | 0.0468 (5) | |
C8 | 0.60216 (15) | 0.2721 (3) | 0.17223 (16) | 0.0480 (5) | |
C9 | 0.49560 (14) | 0.2738 (3) | 0.11632 (15) | 0.0454 (5) | |
C10 | 0.44256 (13) | 0.4362 (3) | 0.10011 (16) | 0.0462 (5) | |
C11 | 0.49896 (16) | 0.5903 (3) | 0.13802 (17) | 0.0495 (5) | |
C12 | 0.60412 (15) | 0.5870 (3) | 0.19153 (17) | 0.0475 (5) | |
C13 | 0.8074 (2) | 0.5919 (3) | 0.3344 (2) | 0.0703 (7) | |
C14 | 0.75993 (18) | 0.7459 (4) | 0.2608 (3) | 0.0692 (7) | |
C15 | 0.33504 (15) | 0.4412 (3) | 0.04695 (18) | 0.0549 (6) | |
C16 | 0.43970 (15) | 0.1197 (3) | 0.07702 (17) | 0.0518 (5) | |
H1 | 0.7623 (18) | 0.227 (3) | 0.111 (2) | 0.066 (7)* | |
H2 | 0.874 (2) | 0.008 (4) | 0.110 (3) | 0.104 (10)* | |
H3 | 1.023 (2) | −0.054 (4) | 0.286 (2) | 0.097 (9)* | |
H4 | 1.042 (2) | 0.094 (3) | 0.448 (2) | 0.088 (8)* | |
H5 | 0.9188 (19) | 0.312 (4) | 0.443 (2) | 0.090 (9)* | |
H8 | 0.6353 (16) | 0.159 (3) | 0.1848 (17) | 0.062 (6)* | |
H11 | 0.4671 (15) | 0.701 (3) | 0.1269 (17) | 0.055 (6)* | |
H13A | 0.794 (2) | 0.595 (4) | 0.407 (2) | 0.096 (9)* | |
H13B | 0.880 (2) | 0.589 (3) | 0.354 (2) | 0.080 (8)* | |
H14A | 0.7830 (18) | 0.862 (4) | 0.302 (2) | 0.078 (7)* | |
H14B | 0.7744 (19) | 0.746 (3) | 0.191 (2) | 0.086 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0565 (9) | 0.0470 (10) | 0.0822 (11) | −0.0062 (7) | 0.0260 (8) | −0.0080 (8) |
N1 | 0.0380 (10) | 0.0594 (12) | 0.0713 (12) | 0.0003 (8) | 0.0136 (9) | −0.0161 (9) |
N2 | 0.0488 (12) | 0.0948 (17) | 0.0884 (15) | 0.0059 (11) | 0.0193 (10) | 0.0200 (13) |
N3 | 0.0603 (12) | 0.0595 (12) | 0.0818 (14) | −0.0070 (9) | 0.0221 (10) | −0.0076 (11) |
C1 | 0.0478 (12) | 0.0518 (14) | 0.0644 (15) | −0.0007 (10) | 0.0236 (11) | 0.0022 (11) |
C2 | 0.0649 (15) | 0.0565 (15) | 0.097 (2) | 0.0020 (12) | 0.0476 (15) | 0.0001 (14) |
C3 | 0.0569 (15) | 0.0696 (18) | 0.124 (3) | 0.0190 (14) | 0.0486 (17) | 0.0229 (18) |
C4 | 0.0474 (14) | 0.099 (2) | 0.091 (2) | 0.0191 (14) | 0.0219 (14) | 0.0315 (18) |
C5 | 0.0464 (13) | 0.092 (2) | 0.0637 (15) | 0.0042 (13) | 0.0160 (11) | 0.0059 (15) |
C6 | 0.0368 (10) | 0.0540 (13) | 0.0619 (13) | −0.0002 (9) | 0.0195 (9) | 0.0007 (10) |
C7 | 0.0397 (11) | 0.0526 (13) | 0.0473 (11) | −0.0010 (9) | 0.0175 (9) | −0.0033 (9) |
C8 | 0.0421 (11) | 0.0470 (14) | 0.0529 (12) | 0.0038 (10) | 0.0181 (9) | 0.0019 (10) |
C9 | 0.0430 (11) | 0.0467 (11) | 0.0463 (11) | 0.0001 (8) | 0.0185 (9) | 0.0011 (9) |
C10 | 0.0425 (11) | 0.0510 (13) | 0.0446 (11) | 0.0018 (9) | 0.0178 (9) | 0.0043 (9) |
C11 | 0.0526 (13) | 0.0460 (14) | 0.0514 (12) | 0.0082 (10) | 0.0233 (10) | 0.0061 (10) |
C12 | 0.0485 (12) | 0.0446 (13) | 0.0513 (12) | −0.0019 (9) | 0.0229 (10) | −0.0023 (9) |
C13 | 0.0487 (14) | 0.0709 (18) | 0.0824 (18) | −0.0082 (12) | 0.0188 (13) | −0.0256 (14) |
C14 | 0.0593 (15) | 0.0638 (17) | 0.0889 (18) | −0.0157 (12) | 0.0356 (13) | −0.0175 (15) |
C15 | 0.0434 (12) | 0.0604 (14) | 0.0577 (13) | 0.0066 (10) | 0.0181 (10) | 0.0105 (11) |
C16 | 0.0452 (11) | 0.0514 (11) | 0.0558 (12) | −0.0005 (8) | 0.0184 (9) | −0.0023 (10) |
Geometric parameters (Å, º) top
C2—C3 | 1.375 (4) | C12—C7 | 1.411 (3) |
C2—C1 | 1.382 (3) | N1—C7 | 1.378 (2) |
C2—H2 | 1.02 (3) | N1—C13 | 1.465 (3) |
C1—C6 | 1.386 (3) | C13—H13B | 0.96 (3) |
C1—H1 | 0.94 (2) | C13—H13A | 1.05 (3) |
C3—C4 | 1.371 (4) | C11—C10 | 1.389 (3) |
C3—H3 | 0.98 (3) | C11—H11 | 0.94 (2) |
C14—O1 | 1.434 (3) | C7—C8 | 1.396 (3) |
C14—C13 | 1.486 (4) | C5—H5 | 0.98 (3) |
C14—H14B | 1.03 (3) | C10—C15 | 1.403 (3) |
C14—H14A | 1.02 (3) | C10—C9 | 1.416 (3) |
O1—C12 | 1.360 (2) | C8—C9 | 1.392 (3) |
C6—C5 | 1.392 (3) | C8—H8 | 0.96 (2) |
C6—N1 | 1.416 (3) | C15—N2 | 1.154 (3) |
C4—C5 | 1.374 (4) | C9—C16 | 1.388 (2) |
C4—H4 | 0.97 (3) | C16—N3 | 1.163 (3) |
C12—C11 | 1.373 (3) | | |
| | | |
C3—C2—C1 | 120.8 (3) | C6—N1—C13 | 119.27 (17) |
C3—C2—H2 | 123.4 (17) | N1—C13—C14 | 109.5 (2) |
C1—C2—H2 | 115.8 (17) | N1—C13—H13B | 107.3 (15) |
C2—C1—C6 | 119.9 (2) | C14—C13—H13B | 109.9 (15) |
C2—C1—H1 | 120.9 (14) | N1—C13—H13A | 108.6 (15) |
C6—C1—H1 | 119.2 (14) | C14—C13—H13A | 111.2 (15) |
C4—C3—C2 | 119.4 (3) | H13B—C13—H13A | 110 (2) |
C4—C3—H3 | 119.6 (16) | C12—C11—C10 | 121.3 (2) |
C2—C3—H3 | 121.0 (16) | C12—C11—H11 | 117.2 (13) |
O1—C14—C13 | 110.3 (2) | C10—C11—H11 | 121.5 (13) |
O1—C14—H14B | 108.7 (14) | N1—C7—C8 | 123.38 (19) |
C13—C14—H14B | 111.8 (15) | N1—C7—C12 | 119.08 (19) |
O1—C14—H14A | 103.8 (13) | C8—C7—C12 | 117.48 (18) |
C13—C14—H14A | 112.0 (14) | C4—C5—C6 | 120.3 (3) |
H14B—C14—H14A | 110 (2) | C4—C5—H5 | 122.9 (15) |
C12—O1—C14 | 115.36 (18) | C6—C5—H5 | 116.8 (15) |
C1—C6—C5 | 118.9 (2) | C11—C10—C15 | 120.7 (2) |
C1—C6—N1 | 121.38 (19) | C11—C10—C9 | 118.75 (17) |
C5—C6—N1 | 119.6 (2) | C15—C10—C9 | 120.55 (18) |
C3—C4—C5 | 120.8 (3) | C9—C8—C7 | 121.9 (2) |
C3—C4—H4 | 118.2 (16) | C9—C8—H8 | 117.1 (13) |
C5—C4—H4 | 121.0 (16) | C7—C8—H8 | 120.9 (13) |
O1—C12—C11 | 116.05 (19) | N2—C15—C10 | 179.2 (2) |
O1—C12—C7 | 122.75 (17) | C16—C9—C8 | 121.60 (19) |
C11—C12—C7 | 121.2 (2) | C16—C9—C10 | 119.02 (17) |
C7—N1—C6 | 124.51 (18) | C8—C9—C10 | 119.37 (18) |
C7—N1—C13 | 116.16 (18) | N3—C16—C9 | 177.6 (2) |
| | | |
C3—C2—C1—C6 | −1.5 (4) | C6—N1—C7—C12 | −163.4 (2) |
C1—C2—C3—C4 | 1.4 (4) | C13—N1—C7—C12 | 13.7 (3) |
C13—C14—O1—C12 | −44.9 (3) | O1—C12—C7—N1 | 2.7 (3) |
C2—C1—C6—C5 | −0.1 (3) | C11—C12—C7—N1 | −175.27 (19) |
C2—C1—C6—N1 | 175.5 (2) | O1—C12—C7—C8 | −179.88 (18) |
C2—C3—C4—C5 | 0.4 (4) | C11—C12—C7—C8 | 2.1 (3) |
C14—O1—C12—C11 | −167.9 (2) | C3—C4—C5—C6 | −2.1 (4) |
C14—O1—C12—C7 | 14.0 (3) | C1—C6—C5—C4 | 1.9 (4) |
C1—C6—N1—C7 | 42.6 (3) | N1—C6—C5—C4 | −173.8 (2) |
C5—C6—N1—C7 | −141.9 (2) | C12—C11—C10—C15 | 179.1 (2) |
C1—C6—N1—C13 | −134.5 (2) | C12—C11—C10—C9 | −0.8 (3) |
C5—C6—N1—C13 | 41.1 (3) | N1—C7—C8—C9 | 176.14 (19) |
C7—N1—C13—C14 | −44.1 (3) | C12—C7—C8—C9 | −1.1 (3) |
C6—N1—C13—C14 | 133.2 (2) | C7—C8—C9—C16 | 179.97 (19) |
O1—C14—C13—N1 | 59.4 (3) | C7—C8—C9—C10 | −0.8 (3) |
O1—C12—C11—C10 | −179.32 (18) | C11—C10—C9—C16 | −178.99 (19) |
C7—C12—C11—C10 | −1.2 (3) | C15—C10—C9—C16 | 1.1 (3) |
C6—N1—C7—C8 | 19.4 (3) | C11—C10—C9—C8 | 1.7 (3) |
C13—N1—C7—C8 | −163.5 (2) | C15—C10—C9—C8 | −178.14 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···N3i | 0.94 (2) | 2.52 (2) | 3.425 (3) | 163 (2) |
Symmetry code: (i) x, y+1, z. |