Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502982X/ac6199sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680502982X/ac6199Isup2.hkl |
CCDC reference: 287431
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.202
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 6.31 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 N1 -C9 -C10 -C11 18.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N1 -C9 -C10 -C8 2.00 5.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was prepared by the reaction of 1-naphthol (5 mmol) with malononitrile (5 mmol) and 4-methoxybenzaldehyde (5 mmol) in ethanol (4 ml) using piperidine as catalyst under microwave irradiation. Pure compound (I) was obtained by recrystallization from ethanol (m.p. 464–466 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 8.23 (d, 1H), 7.88 (d, 1H), 7.55–7.65 (m, 3H), 7.16 (d, 2H), 7.08–7.10 (m, 3H), 6.87 (d, 2H), 4.84 (s, 1H), 3.71(s, 3H).
The N-bound H atoms were located in a difference Fourier map and refined freely. The C-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C). Cg1 is the centroid of atoms O2/C11/C10/C8/C21/C12 ring.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
| Fig. 1. The molecular structure of (I). Fig. 2. The C—H···π interactions in (I), shown as dashed lines. |
C21H16N2O2 | Z = 2 |
Mr = 328.36 | F(000) = 344 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4140 (13) Å | Cell parameters from 25 reflections |
b = 10.643 (2) Å | θ = 10–12° |
c = 13.308 (3) Å | µ = 0.08 mm−1 |
α = 108.59 (3)° | T = 293 K |
β = 96.11 (3)° | Block, colourless |
γ = 96.95 (3)° | 0.4 × 0.4 × 0.2 mm |
V = 844.5 (3) Å3 |
Nonius CAD4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 1.6° |
Graphite monochromator | h = 0→7 |
ω/2θ scans | k = −12→12 |
3594 measured reflections | l = −15→15 |
3287 independent reflections | 3 standard reflections every 200 reflections |
2023 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.202 | w = 1/[σ2(Fo2) + (0.130P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3287 reflections | Δρmax = 0.22 e Å−3 |
235 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.051 (10) |
C21H16N2O2 | γ = 96.95 (3)° |
Mr = 328.36 | V = 844.5 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4140 (13) Å | Mo Kα radiation |
b = 10.643 (2) Å | µ = 0.08 mm−1 |
c = 13.308 (3) Å | T = 293 K |
α = 108.59 (3)° | 0.4 × 0.4 × 0.2 mm |
β = 96.11 (3)° |
Nonius CAD4 diffractometer | Rint = 0.018 |
3594 measured reflections | 3 standard reflections every 200 reflections |
3287 independent reflections | intensity decay: none |
2023 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.202 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.22 e Å−3 |
3287 reflections | Δρmin = −0.20 e Å−3 |
235 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3695 (3) | 0.29973 (17) | 0.88148 (15) | 0.0798 (6) | |
O2 | 0.3768 (2) | 0.96617 (15) | 0.76767 (12) | 0.0596 (5) | |
N1 | 1.0298 (3) | 0.8649 (2) | 0.90388 (17) | 0.0732 (6) | |
N2 | 0.6335 (4) | 1.0832 (2) | 0.90233 (19) | 0.0730 (7) | |
C1 | 0.1913 (6) | 0.2915 (3) | 0.9340 (3) | 0.0948 (10) | |
H1A | 0.1838 | 0.2138 | 0.9562 | 0.142* | |
H1B | 0.0644 | 0.2843 | 0.8858 | 0.142* | |
H1C | 0.2044 | 0.3708 | 0.9958 | 0.142* | |
C2 | 0.4087 (4) | 0.4050 (2) | 0.84362 (18) | 0.0575 (6) | |
C3 | 0.5833 (4) | 0.4082 (2) | 0.7921 (2) | 0.0662 (7) | |
H3A | 0.6680 | 0.3418 | 0.7854 | 0.079* | |
C4 | 0.6333 (4) | 0.5090 (2) | 0.75041 (18) | 0.0596 (6) | |
H4A | 0.7515 | 0.5095 | 0.7156 | 0.072* | |
C5 | 0.5112 (3) | 0.6098 (2) | 0.75921 (16) | 0.0489 (5) | |
C6 | 0.3385 (4) | 0.6054 (2) | 0.8116 (2) | 0.0641 (7) | |
H6A | 0.2543 | 0.6721 | 0.8188 | 0.077* | |
C7 | 0.2859 (4) | 0.5047 (2) | 0.8542 (2) | 0.0663 (7) | |
H7A | 0.1686 | 0.5045 | 0.8896 | 0.080* | |
C8 | 0.5679 (3) | 0.7229 (2) | 0.71396 (17) | 0.0522 (5) | |
H8A | 0.6749 | 0.6973 | 0.6672 | 0.063* | |
C9 | 0.8644 (3) | 0.8632 (2) | 0.85951 (17) | 0.0552 (6) | |
C10 | 0.6619 (3) | 0.8549 (2) | 0.80195 (17) | 0.0511 (5) | |
C11 | 0.5645 (3) | 0.9638 (2) | 0.82482 (18) | 0.0518 (6) | |
C12 | 0.2888 (3) | 0.8560 (2) | 0.67716 (17) | 0.0500 (5) | |
C13 | 0.0966 (3) | 0.8720 (2) | 0.62116 (17) | 0.0515 (6) | |
C14 | 0.0004 (4) | 0.9869 (3) | 0.6559 (2) | 0.0654 (7) | |
H14A | 0.0648 | 1.0587 | 0.7165 | 0.079* | |
C15 | −0.1895 (4) | 0.9931 (3) | 0.6002 (2) | 0.0802 (8) | |
H15A | −0.2534 | 1.0689 | 0.6241 | 0.096* | |
C16 | −0.2875 (4) | 0.8869 (4) | 0.5082 (2) | 0.0853 (9) | |
H16A | −0.4164 | 0.8923 | 0.4719 | 0.102* | |
C17 | −0.1960 (4) | 0.7764 (3) | 0.4717 (2) | 0.0747 (8) | |
H17A | −0.2616 | 0.7068 | 0.4098 | 0.090* | |
C18 | −0.0010 (4) | 0.7655 (3) | 0.52681 (18) | 0.0601 (6) | |
C19 | 0.0974 (4) | 0.6512 (3) | 0.49201 (19) | 0.0688 (7) | |
H19A | 0.0391 | 0.5827 | 0.4281 | 0.083* | |
C20 | 0.2775 (4) | 0.6397 (3) | 0.55075 (19) | 0.0671 (7) | |
H20A | 0.3371 | 0.5621 | 0.5268 | 0.081* | |
C21 | 0.3760 (3) | 0.7425 (2) | 0.64717 (17) | 0.0520 (5) | |
H2 | 0.545 (5) | 1.150 (3) | 0.907 (2) | 0.085 (8)* | |
H1 | 0.736 (4) | 1.093 (3) | 0.957 (2) | 0.075 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0924 (14) | 0.0657 (11) | 0.0920 (13) | 0.0153 (9) | 0.0074 (11) | 0.0424 (10) |
O2 | 0.0426 (8) | 0.0589 (9) | 0.0726 (10) | 0.0102 (7) | −0.0128 (7) | 0.0216 (8) |
N1 | 0.0501 (12) | 0.0875 (15) | 0.0769 (14) | 0.0247 (10) | −0.0083 (10) | 0.0216 (11) |
N2 | 0.0623 (13) | 0.0573 (13) | 0.0858 (15) | 0.0123 (10) | −0.0251 (12) | 0.0164 (11) |
C1 | 0.109 (2) | 0.086 (2) | 0.101 (2) | 0.0000 (17) | 0.0209 (19) | 0.0514 (18) |
C2 | 0.0616 (14) | 0.0521 (13) | 0.0582 (13) | 0.0104 (10) | −0.0039 (11) | 0.0214 (10) |
C3 | 0.0668 (15) | 0.0629 (14) | 0.0730 (15) | 0.0296 (12) | 0.0022 (12) | 0.0245 (12) |
C4 | 0.0497 (13) | 0.0691 (15) | 0.0632 (13) | 0.0242 (11) | 0.0089 (10) | 0.0211 (11) |
C5 | 0.0405 (11) | 0.0539 (12) | 0.0522 (12) | 0.0138 (9) | 0.0019 (9) | 0.0170 (9) |
C6 | 0.0600 (14) | 0.0611 (14) | 0.0860 (16) | 0.0296 (11) | 0.0237 (13) | 0.0340 (12) |
C7 | 0.0616 (15) | 0.0667 (15) | 0.0806 (16) | 0.0169 (12) | 0.0223 (12) | 0.0325 (13) |
C8 | 0.0390 (11) | 0.0617 (13) | 0.0571 (12) | 0.0113 (9) | 0.0057 (9) | 0.0211 (10) |
C9 | 0.0466 (12) | 0.0604 (13) | 0.0609 (13) | 0.0148 (10) | 0.0042 (10) | 0.0227 (11) |
C10 | 0.0355 (10) | 0.0590 (13) | 0.0612 (13) | 0.0075 (9) | −0.0015 (9) | 0.0265 (10) |
C11 | 0.0369 (11) | 0.0558 (13) | 0.0629 (13) | 0.0024 (9) | −0.0050 (9) | 0.0263 (11) |
C12 | 0.0390 (11) | 0.0576 (13) | 0.0551 (12) | 0.0010 (9) | −0.0013 (9) | 0.0264 (10) |
C13 | 0.0374 (11) | 0.0680 (14) | 0.0565 (12) | 0.0018 (10) | 0.0007 (9) | 0.0356 (11) |
C14 | 0.0478 (13) | 0.0762 (16) | 0.0789 (16) | 0.0125 (11) | −0.0031 (12) | 0.0383 (13) |
C15 | 0.0526 (14) | 0.105 (2) | 0.098 (2) | 0.0235 (14) | −0.0020 (14) | 0.0545 (18) |
C16 | 0.0439 (14) | 0.125 (3) | 0.100 (2) | 0.0134 (15) | −0.0094 (14) | 0.061 (2) |
C17 | 0.0486 (14) | 0.107 (2) | 0.0709 (16) | −0.0033 (14) | −0.0101 (12) | 0.0456 (15) |
C18 | 0.0449 (12) | 0.0793 (16) | 0.0620 (14) | −0.0005 (11) | −0.0013 (10) | 0.0387 (12) |
C19 | 0.0595 (15) | 0.0812 (17) | 0.0556 (14) | −0.0027 (13) | −0.0064 (12) | 0.0191 (12) |
C20 | 0.0644 (15) | 0.0715 (16) | 0.0592 (14) | 0.0120 (12) | 0.0015 (12) | 0.0157 (12) |
C21 | 0.0420 (11) | 0.0615 (13) | 0.0555 (12) | 0.0058 (9) | 0.0036 (10) | 0.0261 (10) |
O1—C2 | 1.375 (3) | C8—C21 | 1.515 (3) |
O1—C1 | 1.410 (4) | C8—C10 | 1.518 (3) |
O2—C11 | 1.361 (2) | C8—H8A | 0.9800 |
O2—C12 | 1.393 (3) | C9—C10 | 1.414 (3) |
N1—C9 | 1.153 (3) | C10—C11 | 1.348 (3) |
N2—C11 | 1.344 (3) | C12—C21 | 1.354 (3) |
N2—H2 | 0.96 (3) | C12—C13 | 1.429 (3) |
N2—H1 | 0.90 (3) | C13—C14 | 1.405 (3) |
C1—H1A | 0.9600 | C13—C18 | 1.417 (3) |
C1—H1B | 0.9600 | C14—C15 | 1.377 (3) |
C1—H1C | 0.9600 | C14—H14A | 0.9300 |
C2—C3 | 1.376 (3) | C15—C16 | 1.398 (4) |
C2—C7 | 1.377 (3) | C15—H15A | 0.9300 |
C3—C4 | 1.378 (3) | C16—C17 | 1.352 (4) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.385 (3) | C17—C18 | 1.417 (3) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.374 (3) | C18—C19 | 1.407 (4) |
C5—C8 | 1.532 (3) | C19—C20 | 1.365 (3) |
C6—C7 | 1.387 (3) | C19—H19A | 0.9300 |
C6—H6A | 0.9300 | C20—C21 | 1.417 (3) |
C7—H7A | 0.9300 | C20—H20A | 0.9300 |
C2—O1—C1 | 118.5 (2) | C11—C10—C9 | 119.4 (2) |
C11—O2—C12 | 119.09 (16) | C11—C10—C8 | 123.13 (18) |
C11—N2—H2 | 116.3 (17) | C9—C10—C8 | 117.47 (18) |
C11—N2—H1 | 121.3 (16) | N2—C11—C10 | 127.1 (2) |
H2—N2—H1 | 120 (2) | N2—C11—O2 | 110.26 (18) |
O1—C1—H1A | 109.5 | C10—C11—O2 | 122.6 (2) |
O1—C1—H1B | 109.5 | C21—C12—O2 | 122.50 (18) |
H1A—C1—H1B | 109.5 | C21—C12—C13 | 123.3 (2) |
O1—C1—H1C | 109.5 | O2—C12—C13 | 114.15 (18) |
H1A—C1—H1C | 109.5 | C14—C13—C18 | 119.1 (2) |
H1B—C1—H1C | 109.5 | C14—C13—C12 | 123.1 (2) |
O1—C2—C3 | 116.3 (2) | C18—C13—C12 | 117.8 (2) |
O1—C2—C7 | 124.4 (2) | C15—C14—C13 | 119.9 (2) |
C3—C2—C7 | 119.3 (2) | C15—C14—H14A | 120.0 |
C2—C3—C4 | 120.4 (2) | C13—C14—H14A | 120.0 |
C2—C3—H3A | 119.8 | C14—C15—C16 | 120.9 (3) |
C4—C3—H3A | 119.8 | C14—C15—H15A | 119.5 |
C3—C4—C5 | 121.4 (2) | C16—C15—H15A | 119.5 |
C3—C4—H4A | 119.3 | C17—C16—C15 | 120.4 (2) |
C5—C4—H4A | 119.3 | C17—C16—H16A | 119.8 |
C6—C5—C4 | 117.3 (2) | C15—C16—H16A | 119.8 |
C6—C5—C8 | 121.15 (18) | C16—C17—C18 | 120.6 (3) |
C4—C5—C8 | 121.51 (19) | C16—C17—H17A | 119.7 |
C5—C6—C7 | 122.0 (2) | C18—C17—H17A | 119.7 |
C5—C6—H6A | 119.0 | C19—C18—C13 | 118.7 (2) |
C7—C6—H6A | 119.0 | C19—C18—C17 | 122.2 (2) |
C2—C7—C6 | 119.6 (2) | C13—C18—C17 | 119.0 (2) |
C2—C7—H7A | 120.2 | C20—C19—C18 | 120.9 (2) |
C6—C7—H7A | 120.2 | C20—C19—H19A | 119.6 |
C21—C8—C10 | 109.44 (17) | C18—C19—H19A | 119.6 |
C21—C8—C5 | 111.38 (16) | C19—C20—C21 | 121.9 (2) |
C10—C8—C5 | 111.96 (17) | C19—C20—H20A | 119.1 |
C21—C8—H8A | 108.0 | C21—C20—H20A | 119.1 |
C10—C8—H8A | 108.0 | C12—C21—C20 | 117.2 (2) |
C5—C8—H8A | 108.0 | C12—C21—C8 | 122.2 (2) |
N1—C9—C10 | 177.3 (2) | C20—C21—C8 | 120.52 (19) |
C1—O1—C2—C3 | −179.5 (2) | C11—O2—C12—C13 | −177.54 (17) |
C1—O1—C2—C7 | 0.5 (4) | C21—C12—C13—C14 | 176.3 (2) |
O1—C2—C3—C4 | 179.2 (2) | O2—C12—C13—C14 | −2.0 (3) |
C7—C2—C3—C4 | −0.8 (4) | C21—C12—C13—C18 | −3.0 (3) |
C2—C3—C4—C5 | 0.3 (4) | O2—C12—C13—C18 | 178.74 (17) |
C3—C4—C5—C6 | 0.2 (3) | C18—C13—C14—C15 | 1.9 (3) |
C3—C4—C5—C8 | 179.3 (2) | C12—C13—C14—C15 | −177.4 (2) |
C4—C5—C6—C7 | −0.2 (3) | C13—C14—C15—C16 | −0.8 (4) |
C8—C5—C6—C7 | −179.3 (2) | C14—C15—C16—C17 | −0.6 (4) |
O1—C2—C7—C6 | −179.2 (2) | C15—C16—C17—C18 | 0.9 (4) |
C3—C2—C7—C6 | 0.8 (4) | C14—C13—C18—C19 | 179.4 (2) |
C5—C6—C7—C2 | −0.3 (4) | C12—C13—C18—C19 | −1.2 (3) |
C6—C5—C8—C21 | −49.6 (3) | C14—C13—C18—C17 | −1.6 (3) |
C4—C5—C8—C21 | 131.3 (2) | C12—C13—C18—C17 | 177.71 (19) |
C6—C5—C8—C10 | 73.3 (2) | C16—C17—C18—C19 | 179.2 (2) |
C4—C5—C8—C10 | −105.8 (2) | C16—C17—C18—C13 | 0.2 (4) |
N1—C9—C10—C11 | −176 (100) | C13—C18—C19—C20 | 3.4 (4) |
N1—C9—C10—C8 | 2 (5) | C17—C18—C19—C20 | −175.5 (2) |
C21—C8—C10—C11 | 9.8 (3) | C18—C19—C20—C21 | −1.7 (4) |
C5—C8—C10—C11 | −114.2 (2) | O2—C12—C21—C20 | −177.11 (19) |
C21—C8—C10—C9 | −168.21 (18) | C13—C12—C21—C20 | 4.7 (3) |
C5—C8—C10—C9 | 67.8 (2) | O2—C12—C21—C8 | 4.3 (3) |
C9—C10—C11—N2 | −3.5 (4) | C13—C12—C21—C8 | −173.90 (18) |
C8—C10—C11—N2 | 178.5 (2) | C19—C20—C21—C12 | −2.4 (3) |
C9—C10—C11—O2 | 175.18 (19) | C19—C20—C21—C8 | 176.3 (2) |
C8—C10—C11—O2 | −2.8 (3) | C10—C8—C21—C12 | −10.4 (3) |
C12—O2—C11—N2 | 174.00 (18) | C5—C8—C21—C12 | 113.9 (2) |
C12—O2—C11—C10 | −4.9 (3) | C10—C8—C21—C20 | 170.99 (19) |
C11—O2—C12—C21 | 4.2 (3) | C5—C8—C21—C20 | −64.7 (3) |
Experimental details
Crystal data | |
Chemical formula | C21H16N2O2 |
Mr | 328.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.4140 (13), 10.643 (2), 13.308 (3) |
α, β, γ (°) | 108.59 (3), 96.11 (3), 96.95 (3) |
V (Å3) | 844.5 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.4 × 0.4 × 0.2 |
Data collection | |
Diffractometer | Nonius CAD4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3594, 3287, 2023 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.202, 1.02 |
No. of reflections | 3287 |
No. of parameters | 235 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
O1—C2 | 1.375 (3) | N1—C9 | 1.153 (3) |
O1—C1 | 1.410 (4) | N2—C11 | 1.344 (3) |
O2—C11 | 1.361 (2) | C5—C8 | 1.532 (3) |
O2—C12 | 1.393 (3) | C9—C10 | 1.414 (3) |
C2—O1—C1 | 118.5 (2) | C9—C10—C8 | 117.47 (18) |
C11—O2—C12 | 119.09 (16) | N2—C11—C10 | 127.1 (2) |
O1—C2—C3 | 116.3 (2) | N2—C11—O2 | 110.26 (18) |
O1—C2—C7 | 124.4 (2) | C10—C11—O2 | 122.6 (2) |
C6—C5—C8 | 121.15 (18) | C21—C12—O2 | 122.50 (18) |
C4—C5—C8 | 121.51 (19) | O2—C12—C13 | 114.15 (18) |
C21—C8—C5 | 111.38 (16) | C14—C13—C12 | 123.1 (2) |
C10—C8—C5 | 111.96 (17) | C19—C18—C17 | 122.2 (2) |
N1—C9—C10 | 177.3 (2) | C20—C21—C8 | 120.52 (19) |
C11—C10—C9 | 119.4 (2) |
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Benzopyrans and their derivatives are important in natural and synthetic organic chemistry owing to their biological and pharmacological properties (Morianka & Takahashi, 1977), such as antisterility (Brooks, 1998) and anticancer activities (Hyana & Saimoto, 1987). In addition, polyfunctionalized benzopyrans constitute the structural unit of a number of natural products and, because of the inherent reactivity of the inbuilt pyran ring, these are versatile synthons (Hatakeyama et al., 1988). We report here the crystal structure of the title compound, (I).
The molecular structure of (I), shown in Fig. 1, exhibits weak intramolecular C—H···π interactions (Fig.2, Table 2), which generate a three-dimensional network.