


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808027256/hk2514sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808027256/hk2514Isup2.hkl |
CCDC reference: 702575
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.052
- wR factor = 0.152
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.64 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 46.00 A 3 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by the reaction of dimedone (2 mmol) with 4-fluorobenzaldehyde (1 mmol) and p-toluidine in water (1 mmol) at 413 K under microwave irradiation (maximum power 140 W, initial power 120 W) for 12 min (yield; 89%). Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.
H atoms were positioned geometrically, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C30H32FNO2 | F(000) = 976 |
Mr = 457.58 | Dx = 1.163 Mg m−3 |
Monoclinic, P21/n | Melting point = 540–541 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1533 (15) Å | Cell parameters from 2294 reflections |
b = 10.9643 (12) Å | θ = 2.3–2.3° |
c = 16.1053 (15) Å | µ = 0.08 mm−1 |
β = 102.317 (2)° | T = 298 K |
V = 2614.2 (5) Å3 | Block, pale yellow |
Z = 4 | 0.37 × 0.25 × 0.21 mm |
Bruker SMART CCD area-detector diffractometer | 4605 independent reflections |
Radiation source: fine-focus sealed tube | 2277 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→18 |
Tmin = 0.972, Tmax = 0.984 | k = −13→12 |
13238 measured reflections | l = −13→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0429P)2 + 1.7217P] where P = (Fo2 + 2Fc2)/3 |
4605 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C30H32FNO2 | V = 2614.2 (5) Å3 |
Mr = 457.58 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.1533 (15) Å | µ = 0.08 mm−1 |
b = 10.9643 (12) Å | T = 298 K |
c = 16.1053 (15) Å | 0.37 × 0.25 × 0.21 mm |
β = 102.317 (2)° |
Bruker SMART CCD area-detector diffractometer | 4605 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2277 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.984 | Rint = 0.045 |
13238 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.18 e Å−3 |
4605 reflections | Δρmin = −0.21 e Å−3 |
307 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 | ||
F1 | 0.73692 (17) | −0.0186 (2) | 0.21288 (18) | 0.1213 (10) | |
N1 | 0.99513 (16) | 0.5507 (2) | 0.20652 (15) | 0.0415 (6) | |
O1 | 0.89407 (16) | 0.3144 (2) | −0.03980 (14) | 0.0634 (7) | |
O2 | 1.13495 (16) | 0.1657 (2) | 0.20291 (16) | 0.0695 (7) | |
C1 | 0.93912 (19) | 0.5309 (2) | 0.12692 (19) | 0.0389 (7) | |
C2 | 0.8806 (2) | 0.6360 (3) | 0.08813 (19) | 0.0485 (8) | |
H2A | 0.9169 | 0.6920 | 0.0628 | 0.058* | |
H2B | 0.8599 | 0.6794 | 0.1329 | 0.058* | |
C3 | 0.7985 (2) | 0.5977 (3) | 0.0204 (2) | 0.0507 (8) | |
C4 | 0.8317 (2) | 0.5133 (3) | −0.0417 (2) | 0.0545 (9) | |
H4A | 0.7797 | 0.4807 | −0.0814 | 0.065* | |
H4B | 0.8668 | 0.5606 | −0.0740 | 0.065* | |
C5 | 0.8883 (2) | 0.4090 (3) | 0.00008 (19) | 0.0442 (8) | |
C6 | 0.93853 (19) | 0.4227 (2) | 0.08715 (18) | 0.0372 (7) | |
C7 | 0.98875 (19) | 0.3129 (2) | 0.12966 (18) | 0.0393 (7) | |
H7 | 1.0187 | 0.2735 | 0.0885 | 0.047* | |
C8 | 1.06046 (19) | 0.3524 (2) | 0.20419 (19) | 0.0398 (7) | |
C9 | 1.1334 (2) | 0.2666 (3) | 0.2352 (2) | 0.0504 (8) | |
C10 | 1.2098 (2) | 0.3074 (3) | 0.3049 (2) | 0.0711 (11) | |
H10A | 1.2559 | 0.3447 | 0.2797 | 0.085* | |
H10B | 1.2364 | 0.2364 | 0.3366 | 0.085* | |
C11 | 1.1820 (3) | 0.3972 (3) | 0.3660 (2) | 0.0678 (11) | |
C12 | 1.1319 (2) | 0.5027 (3) | 0.3152 (2) | 0.0572 (9) | |
H12A | 1.1037 | 0.5516 | 0.3525 | 0.069* | |
H12B | 1.1753 | 0.5540 | 0.2954 | 0.069* | |
C13 | 1.06083 (19) | 0.4636 (2) | 0.24020 (18) | 0.0405 (7) | |
C14 | 0.9980 (2) | 0.6695 (2) | 0.24664 (19) | 0.0405 (7) | |
C15 | 1.0480 (2) | 0.7618 (3) | 0.2215 (2) | 0.0456 (8) | |
H15 | 1.0790 | 0.7485 | 0.1783 | 0.055* | |
C16 | 1.0518 (2) | 0.8741 (3) | 0.2606 (2) | 0.0485 (8) | |
H16 | 1.0857 | 0.9363 | 0.2435 | 0.058* | |
C17 | 1.0058 (2) | 0.8960 (3) | 0.3249 (2) | 0.0498 (8) | |
C18 | 0.9566 (2) | 0.8024 (3) | 0.3491 (2) | 0.0584 (9) | |
H18 | 0.9258 | 0.8153 | 0.3925 | 0.070* | |
C19 | 0.9519 (2) | 0.6893 (3) | 0.3101 (2) | 0.0530 (9) | |
H19 | 0.9177 | 0.6271 | 0.3268 | 0.064* | |
C20 | 1.0093 (3) | 1.0207 (3) | 0.3652 (2) | 0.0731 (11) | |
H20A | 0.9604 | 1.0696 | 0.3347 | 0.110* | |
H20B | 1.0657 | 1.0591 | 0.3633 | 0.110* | |
H20C | 1.0038 | 1.0126 | 0.4232 | 0.110* | |
C21 | 0.9223 (2) | 0.2213 (2) | 0.15367 (18) | 0.0410 (7) | |
C22 | 0.9213 (2) | 0.1009 (3) | 0.1283 (2) | 0.0535 (9) | |
H22 | 0.9627 | 0.0739 | 0.0973 | 0.064* | |
C23 | 0.8588 (3) | 0.0196 (3) | 0.1489 (2) | 0.0692 (11) | |
H23 | 0.8580 | −0.0616 | 0.1321 | 0.083* | |
C24 | 0.7990 (3) | 0.0615 (4) | 0.1941 (3) | 0.0720 (11) | |
C25 | 0.7985 (3) | 0.1776 (4) | 0.2209 (3) | 0.0757 (12) | |
H25 | 0.7572 | 0.2030 | 0.2525 | 0.091* | |
C26 | 0.8606 (2) | 0.2581 (3) | 0.2007 (2) | 0.0563 (9) | |
H26 | 0.8609 | 0.3386 | 0.2191 | 0.068* | |
C27 | 0.7548 (3) | 0.7116 (3) | −0.0263 (2) | 0.0761 (12) | |
H27A | 0.7360 | 0.7657 | 0.0135 | 0.114* | |
H27B | 0.7033 | 0.6881 | −0.0691 | 0.114* | |
H27C | 0.7978 | 0.7524 | −0.0526 | 0.114* | |
C28 | 0.7295 (2) | 0.5314 (3) | 0.0606 (2) | 0.0696 (11) | |
H28A | 0.7564 | 0.4592 | 0.0889 | 0.104* | |
H28B | 0.6781 | 0.5093 | 0.0172 | 0.104* | |
H28C | 0.7105 | 0.5842 | 0.1011 | 0.104* | |
C29 | 1.2664 (3) | 0.4479 (3) | 0.4266 (3) | 0.1137 (19) | |
H29A | 1.2483 | 0.4989 | 0.4684 | 0.171* | |
H29B | 1.3013 | 0.4948 | 0.3948 | 0.171* | |
H29C | 1.3022 | 0.3815 | 0.4544 | 0.171* | |
C30 | 1.1203 (4) | 0.3354 (4) | 0.4167 (3) | 0.1026 (16) | |
H30A | 1.0663 | 0.3081 | 0.3787 | 0.154* | |
H30B | 1.1048 | 0.3925 | 0.4565 | 0.154* | |
H30C | 1.1510 | 0.2668 | 0.4469 | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0961 (19) | 0.1090 (19) | 0.155 (2) | −0.0497 (16) | 0.0192 (17) | 0.0503 (18) |
N1 | 0.0426 (15) | 0.0312 (13) | 0.0459 (16) | 0.0000 (11) | −0.0012 (12) | −0.0048 (11) |
O1 | 0.0785 (18) | 0.0585 (15) | 0.0505 (15) | −0.0079 (13) | 0.0076 (12) | −0.0145 (12) |
O2 | 0.0646 (17) | 0.0463 (14) | 0.0919 (19) | 0.0124 (12) | 0.0039 (14) | −0.0141 (13) |
C1 | 0.0361 (17) | 0.0409 (17) | 0.0382 (19) | −0.0049 (14) | 0.0043 (14) | 0.0037 (14) |
C2 | 0.049 (2) | 0.0423 (17) | 0.051 (2) | 0.0021 (15) | 0.0023 (16) | −0.0008 (15) |
C3 | 0.046 (2) | 0.053 (2) | 0.050 (2) | −0.0016 (17) | 0.0020 (16) | 0.0043 (16) |
C4 | 0.057 (2) | 0.062 (2) | 0.041 (2) | −0.0095 (18) | 0.0010 (16) | 0.0063 (17) |
C5 | 0.046 (2) | 0.0477 (19) | 0.0393 (19) | −0.0125 (16) | 0.0105 (15) | −0.0029 (16) |
C6 | 0.0376 (17) | 0.0364 (16) | 0.0368 (18) | −0.0066 (14) | 0.0062 (14) | −0.0008 (13) |
C7 | 0.0415 (18) | 0.0359 (16) | 0.0404 (18) | −0.0031 (14) | 0.0087 (14) | −0.0067 (14) |
C8 | 0.0363 (18) | 0.0353 (16) | 0.047 (2) | −0.0025 (14) | 0.0062 (15) | −0.0010 (14) |
C9 | 0.046 (2) | 0.0369 (18) | 0.065 (2) | −0.0009 (15) | 0.0051 (17) | −0.0025 (16) |
C10 | 0.061 (2) | 0.050 (2) | 0.089 (3) | 0.0101 (19) | −0.015 (2) | −0.001 (2) |
C11 | 0.081 (3) | 0.046 (2) | 0.062 (2) | 0.004 (2) | −0.018 (2) | 0.0009 (19) |
C12 | 0.060 (2) | 0.0403 (18) | 0.061 (2) | −0.0004 (16) | −0.0105 (18) | −0.0054 (16) |
C13 | 0.0396 (18) | 0.0340 (16) | 0.044 (2) | −0.0022 (14) | 0.0012 (15) | −0.0003 (14) |
C14 | 0.0408 (19) | 0.0330 (16) | 0.044 (2) | 0.0009 (14) | 0.0016 (15) | −0.0054 (14) |
C15 | 0.0439 (19) | 0.0419 (18) | 0.050 (2) | −0.0034 (15) | 0.0084 (15) | −0.0062 (15) |
C16 | 0.049 (2) | 0.0406 (18) | 0.054 (2) | −0.0056 (15) | 0.0059 (17) | 0.0000 (15) |
C17 | 0.052 (2) | 0.0434 (19) | 0.048 (2) | 0.0073 (16) | −0.0028 (17) | −0.0074 (16) |
C18 | 0.064 (2) | 0.058 (2) | 0.056 (2) | 0.0031 (19) | 0.0190 (18) | −0.0095 (18) |
C19 | 0.057 (2) | 0.0455 (19) | 0.058 (2) | −0.0042 (17) | 0.0164 (18) | −0.0023 (16) |
C20 | 0.086 (3) | 0.053 (2) | 0.072 (3) | 0.011 (2) | −0.001 (2) | −0.0208 (19) |
C21 | 0.0423 (19) | 0.0354 (16) | 0.0423 (19) | −0.0061 (14) | 0.0023 (15) | −0.0013 (14) |
C22 | 0.061 (2) | 0.0388 (18) | 0.056 (2) | −0.0052 (17) | 0.0011 (17) | −0.0027 (16) |
C23 | 0.079 (3) | 0.040 (2) | 0.074 (3) | −0.018 (2) | −0.016 (2) | 0.0088 (18) |
C24 | 0.056 (3) | 0.068 (3) | 0.087 (3) | −0.020 (2) | 0.004 (2) | 0.030 (2) |
C25 | 0.065 (3) | 0.074 (3) | 0.094 (3) | −0.002 (2) | 0.030 (2) | 0.022 (2) |
C26 | 0.059 (2) | 0.050 (2) | 0.065 (2) | −0.0017 (17) | 0.0231 (19) | 0.0075 (17) |
C27 | 0.070 (3) | 0.070 (2) | 0.076 (3) | 0.012 (2) | −0.012 (2) | 0.011 (2) |
C28 | 0.047 (2) | 0.091 (3) | 0.069 (3) | −0.006 (2) | 0.0102 (19) | 0.002 (2) |
C29 | 0.120 (4) | 0.060 (3) | 0.116 (4) | 0.016 (3) | −0.074 (3) | −0.015 (3) |
C30 | 0.169 (5) | 0.073 (3) | 0.060 (3) | −0.002 (3) | 0.011 (3) | 0.004 (2) |
F1—C24 | 1.367 (4) | C14—C15 | 1.376 (4) |
N1—C1 | 1.395 (4) | C15—C16 | 1.379 (4) |
N1—C13 | 1.403 (3) | C15—H15 | 0.9300 |
N1—C14 | 1.450 (3) | C16—C17 | 1.386 (4) |
O1—C5 | 1.233 (3) | C16—H16 | 0.9300 |
O2—C9 | 1.225 (3) | C17—C18 | 1.373 (4) |
C1—C6 | 1.347 (4) | C17—C20 | 1.510 (4) |
C1—C2 | 1.506 (4) | C18—C19 | 1.386 (4) |
C2—C3 | 1.528 (4) | C18—H18 | 0.9300 |
C2—H2A | 0.9700 | C19—H19 | 0.9300 |
C2—H2B | 0.9700 | C20—H20A | 0.9600 |
C3—C4 | 1.524 (4) | C20—H20B | 0.9600 |
C3—C28 | 1.527 (4) | C20—H20C | 0.9600 |
C3—C27 | 1.534 (4) | C21—C22 | 1.381 (4) |
C4—C5 | 1.499 (4) | C21—C26 | 1.384 (4) |
C4—H4A | 0.9700 | C22—C23 | 1.391 (4) |
C4—H4B | 0.9700 | C22—H22 | 0.9300 |
C5—C6 | 1.454 (4) | C23—C24 | 1.358 (5) |
C6—C7 | 1.509 (4) | C23—H23 | 0.9300 |
C7—C8 | 1.501 (4) | C24—C25 | 1.344 (5) |
C7—C21 | 1.528 (4) | C25—C26 | 1.378 (4) |
C7—H7 | 0.9800 | C25—H25 | 0.9300 |
C8—C13 | 1.349 (4) | C26—H26 | 0.9300 |
C8—C9 | 1.457 (4) | C27—H27A | 0.9600 |
C9—C10 | 1.498 (4) | C27—H27B | 0.9600 |
C10—C11 | 1.514 (5) | C27—H27C | 0.9600 |
C10—H10A | 0.9700 | C28—H28A | 0.9600 |
C10—H10B | 0.9700 | C28—H28B | 0.9600 |
C11—C12 | 1.523 (4) | C28—H28C | 0.9600 |
C11—C30 | 1.525 (5) | C29—H29A | 0.9600 |
C11—C29 | 1.538 (5) | C29—H29B | 0.9600 |
C12—C13 | 1.499 (4) | C29—H29C | 0.9600 |
C12—H12A | 0.9700 | C30—H30A | 0.9600 |
C12—H12B | 0.9700 | C30—H30B | 0.9600 |
C14—C19 | 1.373 (4) | C30—H30C | 0.9600 |
C1—N1—C13 | 119.5 (2) | C15—C14—N1 | 119.7 (3) |
C1—N1—C14 | 120.3 (2) | C14—C15—C16 | 119.6 (3) |
C13—N1—C14 | 119.2 (2) | C14—C15—H15 | 120.2 |
C6—C1—N1 | 121.0 (3) | C16—C15—H15 | 120.2 |
C6—C1—C2 | 122.2 (3) | C15—C16—C17 | 121.1 (3) |
N1—C1—C2 | 116.8 (2) | C15—C16—H16 | 119.4 |
C1—C2—C3 | 113.8 (2) | C17—C16—H16 | 119.4 |
C1—C2—H2A | 108.8 | C18—C17—C16 | 118.2 (3) |
C3—C2—H2A | 108.8 | C18—C17—C20 | 121.7 (3) |
C1—C2—H2B | 108.8 | C16—C17—C20 | 120.1 (3) |
C3—C2—H2B | 108.8 | C17—C18—C19 | 121.2 (3) |
H2A—C2—H2B | 107.7 | C17—C18—H18 | 119.4 |
C4—C3—C28 | 109.9 (3) | C19—C18—H18 | 119.4 |
C4—C3—C2 | 107.7 (3) | C14—C19—C18 | 119.6 (3) |
C28—C3—C2 | 110.8 (3) | C14—C19—H19 | 120.2 |
C4—C3—C27 | 109.9 (3) | C18—C19—H19 | 120.2 |
C28—C3—C27 | 109.4 (3) | C17—C20—H20A | 109.5 |
C2—C3—C27 | 109.1 (3) | C17—C20—H20B | 109.5 |
C5—C4—C3 | 114.0 (3) | H20A—C20—H20B | 109.5 |
C5—C4—H4A | 108.8 | C17—C20—H20C | 109.5 |
C3—C4—H4A | 108.8 | H20A—C20—H20C | 109.5 |
C5—C4—H4B | 108.8 | H20B—C20—H20C | 109.5 |
C3—C4—H4B | 108.8 | C22—C21—C26 | 118.3 (3) |
H4A—C4—H4B | 107.7 | C22—C21—C7 | 121.3 (3) |
O1—C5—C6 | 120.6 (3) | C26—C21—C7 | 120.4 (3) |
O1—C5—C4 | 120.4 (3) | C21—C22—C23 | 120.5 (3) |
C6—C5—C4 | 119.0 (3) | C21—C22—H22 | 119.7 |
C1—C6—C5 | 119.9 (3) | C23—C22—H22 | 119.7 |
C1—C6—C7 | 122.4 (3) | C24—C23—C22 | 118.5 (3) |
C5—C6—C7 | 117.7 (2) | C24—C23—H23 | 120.8 |
C8—C7—C6 | 109.9 (2) | C22—C23—H23 | 120.8 |
C8—C7—C21 | 113.0 (2) | C25—C24—C23 | 122.8 (3) |
C6—C7—C21 | 110.1 (2) | C25—C24—F1 | 119.1 (4) |
C8—C7—H7 | 107.9 | C23—C24—F1 | 118.1 (4) |
C6—C7—H7 | 107.9 | C24—C25—C26 | 118.7 (4) |
C21—C7—H7 | 107.9 | C24—C25—H25 | 120.6 |
C13—C8—C9 | 120.2 (3) | C26—C25—H25 | 120.6 |
C13—C8—C7 | 122.7 (3) | C25—C26—C21 | 121.2 (3) |
C9—C8—C7 | 117.0 (2) | C25—C26—H26 | 119.4 |
O2—C9—C8 | 121.3 (3) | C21—C26—H26 | 119.4 |
O2—C9—C10 | 120.4 (3) | C3—C27—H27A | 109.5 |
C8—C9—C10 | 118.2 (3) | C3—C27—H27B | 109.5 |
C9—C10—C11 | 113.7 (3) | H27A—C27—H27B | 109.5 |
C9—C10—H10A | 108.8 | C3—C27—H27C | 109.5 |
C11—C10—H10A | 108.8 | H27A—C27—H27C | 109.5 |
C9—C10—H10B | 108.8 | H27B—C27—H27C | 109.5 |
C11—C10—H10B | 108.8 | C3—C28—H28A | 109.5 |
H10A—C10—H10B | 107.7 | C3—C28—H28B | 109.5 |
C10—C11—C12 | 108.8 (3) | H28A—C28—H28B | 109.5 |
C10—C11—C30 | 110.3 (3) | C3—C28—H28C | 109.5 |
C12—C11—C30 | 109.5 (3) | H28A—C28—H28C | 109.5 |
C10—C11—C29 | 109.7 (3) | H28B—C28—H28C | 109.5 |
C12—C11—C29 | 108.6 (3) | C11—C29—H29A | 109.5 |
C30—C11—C29 | 110.0 (4) | C11—C29—H29B | 109.5 |
C13—C12—C11 | 113.9 (3) | H29A—C29—H29B | 109.5 |
C13—C12—H12A | 108.8 | C11—C29—H29C | 109.5 |
C11—C12—H12A | 108.8 | H29A—C29—H29C | 109.5 |
C13—C12—H12B | 108.8 | H29B—C29—H29C | 109.5 |
C11—C12—H12B | 108.8 | C11—C30—H30A | 109.5 |
H12A—C12—H12B | 107.7 | C11—C30—H30B | 109.5 |
C8—C13—N1 | 120.7 (3) | H30A—C30—H30B | 109.5 |
C8—C13—C12 | 122.8 (3) | C11—C30—H30C | 109.5 |
N1—C13—C12 | 116.4 (2) | H30A—C30—H30C | 109.5 |
C19—C14—C15 | 120.2 (3) | H30B—C30—H30C | 109.5 |
C19—C14—N1 | 120.1 (3) | ||
C13—N1—C1—C6 | 9.2 (4) | C30—C11—C12—C13 | −73.3 (4) |
C14—N1—C1—C6 | 177.1 (3) | C29—C11—C12—C13 | 166.6 (3) |
C13—N1—C1—C2 | −170.4 (3) | C9—C8—C13—N1 | 174.7 (3) |
C14—N1—C1—C2 | −2.5 (4) | C7—C8—C13—N1 | −2.9 (4) |
C6—C1—C2—C3 | 21.9 (4) | C9—C8—C13—C12 | −3.1 (5) |
N1—C1—C2—C3 | −158.5 (3) | C7—C8—C13—C12 | 179.4 (3) |
C1—C2—C3—C4 | −49.8 (3) | C1—N1—C13—C8 | −11.6 (4) |
C1—C2—C3—C28 | 70.4 (4) | C14—N1—C13—C8 | −179.6 (3) |
C1—C2—C3—C27 | −169.1 (3) | C1—N1—C13—C12 | 166.3 (3) |
C28—C3—C4—C5 | −68.6 (3) | C14—N1—C13—C12 | −1.7 (4) |
C2—C3—C4—C5 | 52.1 (3) | C11—C12—C13—C8 | −20.7 (5) |
C27—C3—C4—C5 | 170.8 (3) | C11—C12—C13—N1 | 161.5 (3) |
C3—C4—C5—O1 | 155.5 (3) | C1—N1—C14—C19 | 101.5 (3) |
C3—C4—C5—C6 | −26.6 (4) | C13—N1—C14—C19 | −90.5 (3) |
N1—C1—C6—C5 | −172.3 (2) | C1—N1—C14—C15 | −79.2 (4) |
C2—C1—C6—C5 | 7.2 (4) | C13—N1—C14—C15 | 88.8 (3) |
N1—C1—C6—C7 | 7.6 (4) | C19—C14—C15—C16 | 0.3 (5) |
C2—C1—C6—C7 | −172.8 (3) | N1—C14—C15—C16 | −179.0 (3) |
O1—C5—C6—C1 | 173.0 (3) | C14—C15—C16—C17 | −0.2 (5) |
C4—C5—C6—C1 | −4.9 (4) | C15—C16—C17—C18 | 0.3 (5) |
O1—C5—C6—C7 | −6.9 (4) | C15—C16—C17—C20 | −178.5 (3) |
C4—C5—C6—C7 | 175.2 (3) | C16—C17—C18—C19 | −0.6 (5) |
C1—C6—C7—C8 | −19.6 (4) | C20—C17—C18—C19 | 178.3 (3) |
C5—C6—C7—C8 | 160.3 (2) | C15—C14—C19—C18 | −0.5 (5) |
C1—C6—C7—C21 | 105.5 (3) | N1—C14—C19—C18 | 178.8 (3) |
C5—C6—C7—C21 | −74.6 (3) | C17—C18—C19—C14 | 0.7 (5) |
C6—C7—C8—C13 | 17.3 (4) | C8—C7—C21—C22 | −110.1 (3) |
C21—C7—C8—C13 | −106.2 (3) | C6—C7—C21—C22 | 126.5 (3) |
C6—C7—C8—C9 | −160.4 (2) | C8—C7—C21—C26 | 70.8 (4) |
C21—C7—C8—C9 | 76.2 (3) | C6—C7—C21—C26 | −52.6 (4) |
C13—C8—C9—O2 | −179.3 (3) | C26—C21—C22—C23 | 0.8 (5) |
C7—C8—C9—O2 | −1.5 (4) | C7—C21—C22—C23 | −178.3 (3) |
C13—C8—C9—C10 | −2.6 (5) | C21—C22—C23—C24 | 0.2 (5) |
C7—C8—C9—C10 | 175.1 (3) | C22—C23—C24—C25 | −1.1 (6) |
O2—C9—C10—C11 | −151.3 (3) | C22—C23—C24—F1 | 179.0 (3) |
C8—C9—C10—C11 | 32.0 (4) | C23—C24—C25—C26 | 1.0 (6) |
C9—C10—C11—C12 | −53.0 (4) | F1—C24—C25—C26 | −179.2 (3) |
C9—C10—C11—C30 | 67.1 (4) | C24—C25—C26—C21 | 0.1 (6) |
C9—C10—C11—C29 | −171.6 (3) | C22—C21—C26—C25 | −1.0 (5) |
C10—C11—C12—C13 | 47.2 (4) | C7—C21—C26—C25 | 178.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.93 | 2.45 | 3.336 (3) | 159 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C30H32FNO2 |
Mr | 457.58 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 15.1533 (15), 10.9643 (12), 16.1053 (15) |
β (°) | 102.317 (2) |
V (Å3) | 2614.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.37 × 0.25 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.972, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13238, 4605, 2277 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.152, 1.02 |
No. of reflections | 4605 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.93 | 2.45 | 3.336 (3) | 159.00 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acridine derivatives containing 1,4-dihydropyridine unit belong to a special class of compounds not only because of their interesting chemical and physical properties but also due to their immense utility in pharmaceutical and dye industry, and they are well known atherapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychcy, 1979; Thull & Testa, 1994; Reil et al., 1994; Mandi et al., 1994). We have reported the synthesis of N-hydroxylacridine derivatives, previously, (Tu et al., 2004) and we report herein the structure of the title compound.
In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings D (C14-C19) and E (C21-C26) are, of course, planar and they are oriented at a dihedral angle of D/E = 15.33 (3)°. Rings A (C1-C6), B (N1/C1/C6-C8/C13) and C (C8-C13) are not planar, having total puckering amplitudes, QT, of 0.475 (3), 0.201 (2) and 0.448 (3) Å, respectively, and flattened boat conformations [ϕ = -56.70 (3)°, θ = 120.78 (3)°; ϕ = 172.92 (2)°, θ = 76.41 (3)° and ϕ = 170.16 (3)°, θ = 54.52 (3)°, respectively] (Cremer & Pople, 1975).
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.