Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042365/ci2452sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042365/ci2452Isup2.hkl |
CCDC reference: 664191
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.146
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 1 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-methoxybenzaldehyde (1 mmol) and 4-chlorobenzenamine (1 mmol) at 413 K under microwave irradiation (maximum power 150 W, initial power 100 W) for 12 min (yield 85%; m.p. 542–543 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.
H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. Owing to the large number of weak high-angle reflections, the ratio of observed to unique reflections is low (48%).
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 & Brychey, 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 report herein the structure of the title compound.
In the title molecule, the dihydropyridine ring is in a boat conformation, with atoms N1 and C7 deviating from the C1/C6/C8/C13 plane by 0.099 (5) and 0.255 (5) Å, respectively (Fig. 1). Both cyclohexene rings adopt envelope conformations: atom C3 deviaties from the C1/C2/C4/C5/C6 by 0.667 (5) Å and atom C11 deviates from the C8/C9/C10/C12/C13 plane by 0.660 (5) Å. The dihedral angle between the C1/C6/C8/C13 plane and the C14–C29 benzene ring attached at atom N1 is 81.31 (11)° and that between the C1/C6/C8/C13 plane and the C24–C29 benzene ring attached at atom C7 is 88.84 (12)°.
The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 1).
For related literature, see: Mandi et al. (1994); Nasim & Brychey (1979); Reil et al. (1994); Thull & Testa (1994); Tu et al. (2004); Wysocka-Skrzela & Ledochowski (1976).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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 (Bruker, 1997).
Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C30H32ClNO3 | F(000) = 1040 |
Mr = 490.02 | Dx = 1.234 Mg m−3 |
Monoclinic, P21/c | Melting point = 542–543 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.227 (2) Å | Cell parameters from 2397 reflections |
b = 10.883 (2) Å | θ = 2.4–25.4° |
c = 20.178 (3) Å | µ = 0.18 mm−1 |
β = 100.788 (2)° | T = 298 K |
V = 2637.8 (8) Å3 | Block, yellow |
Z = 4 | 0.40 × 0.38 × 0.22 mm |
Bruker SMART CCD area-detector diffractometer | 4516 independent reflections |
Radiation source: fine-focus sealed tube | 2146 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→14 |
Tmin = 0.933, Tmax = 0.962 | k = −12→12 |
10435 measured reflections | l = −24→18 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0416P)2 + 1.2116P] where P = (Fo2 + 2Fc2)/3 |
4516 reflections | (Δ/σ)max = 0.001 |
321 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C30H32ClNO3 | V = 2637.8 (8) Å3 |
Mr = 490.02 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.227 (2) Å | µ = 0.18 mm−1 |
b = 10.883 (2) Å | T = 298 K |
c = 20.178 (3) Å | 0.40 × 0.38 × 0.22 mm |
β = 100.788 (2)° |
Bruker SMART CCD area-detector diffractometer | 4516 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2146 reflections with I > 2σ(I) |
Tmin = 0.933, Tmax = 0.962 | Rint = 0.072 |
10435 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.19 e Å−3 |
4516 reflections | Δρmin = −0.37 e Å−3 |
321 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 | ||
Cl1 | 0.63124 (12) | −0.02238 (10) | 0.23800 (6) | 0.0953 (5) | |
N1 | 0.7981 (2) | 0.4467 (2) | 0.36849 (14) | 0.0383 (7) | |
O1 | 0.9443 (2) | 0.8361 (2) | 0.32608 (14) | 0.0679 (8) | |
O2 | 0.9300 (2) | 0.6883 (2) | 0.56080 (13) | 0.0635 (8) | |
O3 | 0.4979 (2) | 1.0176 (2) | 0.41504 (13) | 0.0618 (8) | |
C1 | 0.8330 (3) | 0.5342 (3) | 0.32568 (17) | 0.0358 (8) | |
C2 | 0.8322 (3) | 0.4956 (3) | 0.25370 (17) | 0.0445 (9) | |
H2A | 0.7686 | 0.4424 | 0.2388 | 0.053* | |
H2B | 0.8989 | 0.4484 | 0.2521 | 0.053* | |
C3 | 0.8266 (3) | 0.6043 (3) | 0.20498 (18) | 0.0458 (10) | |
C4 | 0.9179 (3) | 0.6935 (3) | 0.23476 (19) | 0.0538 (11) | |
H4A | 0.9896 | 0.6548 | 0.2352 | 0.065* | |
H4B | 0.9134 | 0.7653 | 0.2059 | 0.065* | |
C5 | 0.9121 (3) | 0.7340 (3) | 0.30488 (19) | 0.0456 (10) | |
C6 | 0.8679 (3) | 0.6463 (3) | 0.34922 (17) | 0.0372 (9) | |
C7 | 0.8619 (3) | 0.6884 (3) | 0.41955 (17) | 0.0397 (9) | |
H7 | 0.9316 | 0.7309 | 0.4381 | 0.048* | |
C8 | 0.8520 (3) | 0.5780 (3) | 0.46365 (17) | 0.0387 (9) | |
C9 | 0.8828 (3) | 0.5939 (3) | 0.53650 (19) | 0.0476 (10) | |
C10 | 0.8585 (3) | 0.4910 (3) | 0.58209 (18) | 0.0546 (11) | |
H10A | 0.8375 | 0.5269 | 0.6219 | 0.066* | |
H10B | 0.9264 | 0.4445 | 0.5968 | 0.066* | |
C11 | 0.7674 (3) | 0.4030 (3) | 0.55013 (17) | 0.0471 (10) | |
C12 | 0.7937 (3) | 0.3617 (3) | 0.48203 (17) | 0.0446 (10) | |
H12A | 0.8586 | 0.3087 | 0.4901 | 0.054* | |
H12B | 0.7316 | 0.3139 | 0.4582 | 0.054* | |
C13 | 0.8154 (3) | 0.4675 (3) | 0.43802 (17) | 0.0365 (8) | |
C14 | 0.7567 (3) | 0.3295 (3) | 0.34056 (17) | 0.0373 (9) | |
C15 | 0.8265 (3) | 0.2303 (3) | 0.34167 (17) | 0.0423 (9) | |
H15 | 0.9005 | 0.2368 | 0.3631 | 0.051* | |
C16 | 0.7876 (4) | 0.1206 (3) | 0.31119 (19) | 0.0518 (11) | |
H16 | 0.8347 | 0.0532 | 0.3127 | 0.062* | |
C17 | 0.6786 (4) | 0.1127 (3) | 0.27868 (19) | 0.0518 (11) | |
C18 | 0.6075 (4) | 0.2106 (4) | 0.27786 (19) | 0.0592 (11) | |
H18 | 0.5335 | 0.2039 | 0.2563 | 0.071* | |
C19 | 0.6465 (3) | 0.3196 (3) | 0.30932 (19) | 0.0508 (10) | |
H19 | 0.5985 | 0.3858 | 0.3094 | 0.061* | |
C20 | 0.7133 (3) | 0.6675 (3) | 0.1972 (2) | 0.0701 (13) | |
H20A | 0.7027 | 0.6976 | 0.2402 | 0.105* | |
H20B | 0.6556 | 0.6096 | 0.1801 | 0.105* | |
H20C | 0.7104 | 0.7349 | 0.1662 | 0.105* | |
C21 | 0.8439 (4) | 0.5572 (3) | 0.13605 (19) | 0.0729 (14) | |
H21A | 0.8441 | 0.6255 | 0.1059 | 0.109* | |
H21B | 0.7847 | 0.5019 | 0.1179 | 0.109* | |
H21C | 0.9139 | 0.5149 | 0.1412 | 0.109* | |
C22 | 0.6529 (3) | 0.4660 (4) | 0.5398 (2) | 0.0684 (13) | |
H22A | 0.6355 | 0.4869 | 0.5828 | 0.103* | |
H22B | 0.5972 | 0.4112 | 0.5164 | 0.103* | |
H22C | 0.6546 | 0.5394 | 0.5135 | 0.103* | |
C23 | 0.7667 (4) | 0.2905 (4) | 0.59582 (19) | 0.0670 (12) | |
H23A | 0.8377 | 0.2502 | 0.6017 | 0.100* | |
H23B | 0.7095 | 0.2346 | 0.5754 | 0.100* | |
H23C | 0.7526 | 0.3164 | 0.6389 | 0.100* | |
C24 | 0.7657 (3) | 0.7782 (3) | 0.41982 (17) | 0.0383 (9) | |
C25 | 0.7838 (3) | 0.8957 (3) | 0.44530 (17) | 0.0451 (10) | |
H25 | 0.8561 | 0.9202 | 0.4632 | 0.054* | |
C26 | 0.6972 (3) | 0.9784 (3) | 0.44502 (18) | 0.0492 (10) | |
H26 | 0.7114 | 1.0567 | 0.4629 | 0.059* | |
C27 | 0.5906 (3) | 0.9430 (3) | 0.41801 (18) | 0.0465 (10) | |
C28 | 0.5696 (3) | 0.8255 (3) | 0.39276 (19) | 0.0536 (11) | |
H28 | 0.4971 | 0.8009 | 0.3753 | 0.064* | |
C29 | 0.6569 (3) | 0.7451 (3) | 0.39361 (19) | 0.0508 (10) | |
H29 | 0.6424 | 0.6665 | 0.3761 | 0.061* | |
C30 | 0.5146 (4) | 1.1371 (3) | 0.4434 (2) | 0.0681 (13) | |
H30A | 0.5551 | 1.1311 | 0.4889 | 0.102* | |
H30B | 0.4438 | 1.1751 | 0.4434 | 0.102* | |
H30C | 0.5562 | 1.1857 | 0.4171 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1363 (12) | 0.0698 (8) | 0.0820 (9) | −0.0530 (8) | 0.0264 (8) | −0.0276 (6) |
N1 | 0.047 (2) | 0.0310 (15) | 0.0380 (18) | −0.0046 (14) | 0.0118 (15) | −0.0043 (13) |
O1 | 0.076 (2) | 0.0475 (16) | 0.083 (2) | −0.0252 (15) | 0.0219 (17) | −0.0111 (15) |
O2 | 0.070 (2) | 0.0567 (17) | 0.0580 (18) | −0.0008 (15) | −0.0039 (15) | −0.0193 (14) |
O3 | 0.0567 (19) | 0.0575 (17) | 0.070 (2) | 0.0176 (15) | 0.0086 (15) | −0.0048 (14) |
C1 | 0.036 (2) | 0.0319 (19) | 0.041 (2) | 0.0021 (16) | 0.0116 (17) | −0.0006 (16) |
C2 | 0.059 (3) | 0.0316 (19) | 0.046 (2) | −0.0010 (18) | 0.0175 (19) | −0.0008 (16) |
C3 | 0.060 (3) | 0.035 (2) | 0.044 (2) | −0.0015 (19) | 0.013 (2) | −0.0003 (17) |
C4 | 0.064 (3) | 0.045 (2) | 0.055 (3) | −0.008 (2) | 0.017 (2) | 0.0015 (19) |
C5 | 0.040 (2) | 0.039 (2) | 0.059 (3) | −0.0022 (19) | 0.011 (2) | −0.0027 (19) |
C6 | 0.037 (2) | 0.0328 (19) | 0.043 (2) | −0.0005 (17) | 0.0107 (18) | −0.0047 (16) |
C7 | 0.036 (2) | 0.037 (2) | 0.046 (2) | −0.0039 (17) | 0.0060 (18) | −0.0081 (17) |
C8 | 0.035 (2) | 0.041 (2) | 0.039 (2) | 0.0012 (18) | 0.0050 (18) | −0.0076 (17) |
C9 | 0.041 (3) | 0.049 (2) | 0.052 (3) | 0.010 (2) | 0.004 (2) | −0.016 (2) |
C10 | 0.056 (3) | 0.063 (3) | 0.043 (2) | 0.011 (2) | 0.004 (2) | −0.002 (2) |
C11 | 0.048 (3) | 0.057 (2) | 0.037 (2) | 0.004 (2) | 0.0087 (19) | −0.0037 (19) |
C12 | 0.045 (2) | 0.042 (2) | 0.047 (2) | 0.0017 (18) | 0.0105 (19) | −0.0033 (18) |
C13 | 0.036 (2) | 0.039 (2) | 0.035 (2) | 0.0034 (17) | 0.0069 (17) | −0.0060 (17) |
C14 | 0.040 (3) | 0.0314 (19) | 0.041 (2) | −0.0039 (18) | 0.0104 (19) | −0.0031 (16) |
C15 | 0.042 (2) | 0.038 (2) | 0.047 (2) | −0.0031 (19) | 0.0085 (19) | −0.0060 (17) |
C16 | 0.063 (3) | 0.037 (2) | 0.058 (3) | −0.001 (2) | 0.020 (2) | −0.0095 (19) |
C17 | 0.070 (3) | 0.045 (2) | 0.043 (2) | −0.020 (2) | 0.017 (2) | −0.0098 (19) |
C18 | 0.046 (3) | 0.078 (3) | 0.051 (3) | −0.023 (2) | 0.002 (2) | −0.006 (2) |
C19 | 0.050 (3) | 0.048 (2) | 0.054 (3) | 0.000 (2) | 0.008 (2) | 0.001 (2) |
C20 | 0.072 (3) | 0.059 (3) | 0.071 (3) | 0.007 (2) | −0.005 (3) | 0.001 (2) |
C21 | 0.127 (4) | 0.049 (2) | 0.046 (3) | −0.006 (3) | 0.026 (3) | 0.0022 (19) |
C22 | 0.047 (3) | 0.091 (3) | 0.072 (3) | 0.011 (2) | 0.023 (2) | 0.000 (2) |
C23 | 0.077 (3) | 0.073 (3) | 0.053 (3) | 0.000 (3) | 0.015 (2) | 0.012 (2) |
C24 | 0.041 (3) | 0.035 (2) | 0.041 (2) | 0.0040 (17) | 0.0114 (19) | −0.0045 (16) |
C25 | 0.045 (3) | 0.039 (2) | 0.051 (2) | −0.0023 (19) | 0.0093 (19) | −0.0066 (18) |
C26 | 0.063 (3) | 0.0286 (19) | 0.057 (3) | 0.001 (2) | 0.015 (2) | −0.0072 (17) |
C27 | 0.049 (3) | 0.044 (2) | 0.048 (2) | 0.011 (2) | 0.012 (2) | 0.0019 (18) |
C28 | 0.039 (3) | 0.061 (3) | 0.060 (3) | −0.001 (2) | 0.008 (2) | −0.016 (2) |
C29 | 0.043 (3) | 0.046 (2) | 0.064 (3) | 0.001 (2) | 0.011 (2) | −0.0189 (19) |
C30 | 0.080 (3) | 0.053 (3) | 0.072 (3) | 0.020 (2) | 0.015 (3) | −0.006 (2) |
Cl1—C17 | 1.730 (4) | C14—C15 | 1.374 (4) |
N1—C13 | 1.398 (4) | C14—C19 | 1.380 (5) |
N1—C1 | 1.405 (4) | C15—C16 | 1.385 (4) |
N1—C14 | 1.447 (4) | C15—H15 | 0.93 |
O1—C5 | 1.228 (4) | C16—C17 | 1.374 (5) |
O2—C9 | 1.234 (4) | C16—H16 | 0.93 |
O3—C27 | 1.387 (4) | C17—C18 | 1.373 (5) |
O3—C30 | 1.420 (4) | C18—C19 | 1.387 (5) |
C1—C6 | 1.349 (4) | C18—H18 | 0.93 |
C1—C2 | 1.510 (4) | C19—H19 | 0.93 |
C2—C3 | 1.532 (4) | C20—H20A | 0.96 |
C2—H2A | 0.97 | C20—H20B | 0.96 |
C2—H2B | 0.97 | C20—H20C | 0.96 |
C3—C4 | 1.517 (5) | C21—H21A | 0.96 |
C3—C20 | 1.528 (5) | C21—H21B | 0.96 |
C3—C21 | 1.534 (5) | C21—H21C | 0.96 |
C4—C5 | 1.496 (5) | C22—H22A | 0.96 |
C4—H4A | 0.97 | C22—H22B | 0.96 |
C4—H4B | 0.97 | C22—H22C | 0.96 |
C5—C6 | 1.478 (5) | C23—H23A | 0.96 |
C6—C7 | 1.506 (4) | C23—H23B | 0.96 |
C7—C8 | 1.513 (4) | C23—H23C | 0.96 |
C7—C24 | 1.530 (4) | C24—C25 | 1.381 (4) |
C7—H7 | 0.98 | C24—C29 | 1.384 (5) |
C8—C13 | 1.352 (4) | C25—C26 | 1.388 (4) |
C8—C9 | 1.458 (5) | C25—H25 | 0.93 |
C9—C10 | 1.513 (5) | C26—C27 | 1.370 (5) |
C10—C11 | 1.519 (5) | C26—H26 | 0.93 |
C10—H10A | 0.97 | C27—C28 | 1.383 (5) |
C10—H10B | 0.97 | C28—C29 | 1.377 (5) |
C11—C23 | 1.533 (5) | C28—H28 | 0.93 |
C11—C12 | 1.536 (5) | C29—H29 | 0.93 |
C11—C22 | 1.537 (5) | C30—H30A | 0.96 |
C12—C13 | 1.508 (4) | C30—H30B | 0.96 |
C12—H12A | 0.97 | C30—H30C | 0.96 |
C12—H12B | 0.97 | ||
C13—N1—C1 | 120.1 (3) | C15—C14—N1 | 121.0 (3) |
C13—N1—C14 | 120.6 (3) | C19—C14—N1 | 119.2 (3) |
C1—N1—C14 | 118.8 (3) | C14—C15—C16 | 120.6 (4) |
C27—O3—C30 | 117.6 (3) | C14—C15—H15 | 119.7 |
C6—C1—N1 | 120.6 (3) | C16—C15—H15 | 119.7 |
C6—C1—C2 | 122.4 (3) | C17—C16—C15 | 119.1 (4) |
N1—C1—C2 | 117.0 (3) | C17—C16—H16 | 120.4 |
C1—C2—C3 | 113.2 (3) | C15—C16—H16 | 120.4 |
C1—C2—H2A | 108.9 | C18—C17—C16 | 120.9 (3) |
C3—C2—H2A | 108.9 | C18—C17—Cl1 | 119.9 (3) |
C1—C2—H2B | 108.9 | C16—C17—Cl1 | 119.2 (3) |
C3—C2—H2B | 108.9 | C17—C18—C19 | 119.7 (4) |
H2A—C2—H2B | 107.8 | C17—C18—H18 | 120.2 |
C4—C3—C20 | 109.8 (3) | C19—C18—H18 | 120.2 |
C4—C3—C2 | 107.4 (3) | C14—C19—C18 | 119.9 (4) |
C20—C3—C2 | 110.2 (3) | C14—C19—H19 | 120.0 |
C4—C3—C21 | 110.9 (3) | C18—C19—H19 | 120.0 |
C20—C3—C21 | 109.5 (3) | C3—C20—H20A | 109.5 |
C2—C3—C21 | 109.1 (3) | C3—C20—H20B | 109.5 |
C5—C4—C3 | 113.7 (3) | H20A—C20—H20B | 109.5 |
C5—C4—H4A | 108.8 | C3—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 | C3—C21—H21A | 109.5 |
H4A—C4—H4B | 107.7 | C3—C21—H21B | 109.5 |
O1—C5—C6 | 120.2 (3) | H21A—C21—H21B | 109.5 |
O1—C5—C4 | 121.8 (3) | C3—C21—H21C | 109.5 |
C6—C5—C4 | 118.0 (3) | H21A—C21—H21C | 109.5 |
C1—C6—C5 | 119.9 (3) | H21B—C21—H21C | 109.5 |
C1—C6—C7 | 122.6 (3) | C11—C22—H22A | 109.5 |
C5—C6—C7 | 117.5 (3) | C11—C22—H22B | 109.5 |
C6—C7—C8 | 109.6 (3) | H22A—C22—H22B | 109.5 |
C6—C7—C24 | 111.8 (3) | C11—C22—H22C | 109.5 |
C8—C7—C24 | 111.0 (3) | H22A—C22—H22C | 109.5 |
C6—C7—H7 | 108.1 | H22B—C22—H22C | 109.5 |
C8—C7—H7 | 108.1 | C11—C23—H23A | 109.5 |
C24—C7—H7 | 108.1 | C11—C23—H23B | 109.5 |
C13—C8—C9 | 119.7 (3) | H23A—C23—H23B | 109.5 |
C13—C8—C7 | 122.6 (3) | C11—C23—H23C | 109.5 |
C9—C8—C7 | 117.7 (3) | H23A—C23—H23C | 109.5 |
O2—C9—C8 | 120.8 (4) | H23B—C23—H23C | 109.5 |
O2—C9—C10 | 120.3 (3) | C25—C24—C29 | 117.3 (3) |
C8—C9—C10 | 118.8 (3) | C25—C24—C7 | 121.6 (3) |
C9—C10—C11 | 114.9 (3) | C29—C24—C7 | 121.2 (3) |
C9—C10—H10A | 108.6 | C24—C25—C26 | 122.0 (4) |
C11—C10—H10A | 108.6 | C24—C25—H25 | 119.0 |
C9—C10—H10B | 108.6 | C26—C25—H25 | 119.0 |
C11—C10—H10B | 108.6 | C27—C26—C25 | 119.1 (3) |
H10A—C10—H10B | 107.5 | C27—C26—H26 | 120.4 |
C10—C11—C23 | 109.5 (3) | C25—C26—H26 | 120.4 |
C10—C11—C12 | 107.7 (3) | C26—C27—C28 | 120.3 (4) |
C23—C11—C12 | 109.3 (3) | C26—C27—O3 | 124.2 (3) |
C10—C11—C22 | 110.7 (3) | C28—C27—O3 | 115.6 (4) |
C23—C11—C22 | 109.4 (3) | C29—C28—C27 | 119.5 (4) |
C12—C11—C22 | 110.3 (3) | C29—C28—H28 | 120.3 |
C13—C12—C11 | 113.1 (3) | C27—C28—H28 | 120.3 |
C13—C12—H12A | 109.0 | C28—C29—C24 | 121.8 (3) |
C11—C12—H12A | 109.0 | C28—C29—H29 | 119.1 |
C13—C12—H12B | 109.0 | C24—C29—H29 | 119.1 |
C11—C12—H12B | 109.0 | O3—C30—H30A | 109.5 |
H12A—C12—H12B | 107.8 | O3—C30—H30B | 109.5 |
C8—C13—N1 | 120.3 (3) | H30A—C30—H30B | 109.5 |
C8—C13—C12 | 122.4 (3) | O3—C30—H30C | 109.5 |
N1—C13—C12 | 117.2 (3) | H30A—C30—H30C | 109.5 |
C15—C14—C19 | 119.7 (3) | H30B—C30—H30C | 109.5 |
C13—N1—C1—C6 | −10.0 (5) | C22—C11—C12—C13 | 69.6 (4) |
C14—N1—C1—C6 | 177.3 (3) | C9—C8—C13—N1 | −172.4 (3) |
C13—N1—C1—C2 | 168.5 (3) | C7—C8—C13—N1 | 8.0 (5) |
C14—N1—C1—C2 | −4.2 (4) | C9—C8—C13—C12 | 6.4 (5) |
C6—C1—C2—C3 | −23.9 (5) | C7—C8—C13—C12 | −173.2 (3) |
N1—C1—C2—C3 | 157.6 (3) | C1—N1—C13—C8 | 8.8 (5) |
C1—C2—C3—C4 | 51.3 (4) | C14—N1—C13—C8 | −178.7 (3) |
C1—C2—C3—C20 | −68.3 (4) | C1—N1—C13—C12 | −170.0 (3) |
C1—C2—C3—C21 | 171.5 (3) | C14—N1—C13—C12 | 2.5 (5) |
C20—C3—C4—C5 | 64.3 (4) | C11—C12—C13—C8 | 25.0 (5) |
C2—C3—C4—C5 | −55.5 (4) | C11—C12—C13—N1 | −156.2 (3) |
C21—C3—C4—C5 | −174.6 (3) | C13—N1—C14—C15 | −79.9 (4) |
C3—C4—C5—O1 | −149.3 (4) | C1—N1—C14—C15 | 92.7 (4) |
C3—C4—C5—C6 | 31.8 (5) | C13—N1—C14—C19 | 103.4 (4) |
N1—C1—C6—C5 | 175.5 (3) | C1—N1—C14—C19 | −84.0 (4) |
C2—C1—C6—C5 | −2.9 (5) | C19—C14—C15—C16 | 0.6 (5) |
N1—C1—C6—C7 | −5.7 (5) | N1—C14—C15—C16 | −176.0 (3) |
C2—C1—C6—C7 | 175.9 (3) | C14—C15—C16—C17 | 1.1 (5) |
O1—C5—C6—C1 | −179.8 (3) | C15—C16—C17—C18 | −2.0 (6) |
C4—C5—C6—C1 | −0.9 (5) | C15—C16—C17—Cl1 | 177.7 (3) |
O1—C5—C6—C7 | 1.4 (5) | C16—C17—C18—C19 | 1.0 (6) |
C4—C5—C6—C7 | −179.7 (3) | Cl1—C17—C18—C19 | −178.6 (3) |
C1—C6—C7—C8 | 19.8 (5) | C15—C14—C19—C18 | −1.5 (5) |
C5—C6—C7—C8 | −161.5 (3) | N1—C14—C19—C18 | 175.2 (3) |
C1—C6—C7—C24 | −103.8 (4) | C17—C18—C19—C14 | 0.7 (6) |
C5—C6—C7—C24 | 75.0 (4) | C6—C7—C24—C25 | −120.9 (4) |
C6—C7—C8—C13 | −21.0 (5) | C8—C7—C24—C25 | 116.4 (4) |
C24—C7—C8—C13 | 103.0 (4) | C6—C7—C24—C29 | 58.3 (4) |
C6—C7—C8—C9 | 159.5 (3) | C8—C7—C24—C29 | −64.5 (4) |
C24—C7—C8—C9 | −76.5 (4) | C29—C24—C25—C26 | 0.0 (5) |
C13—C8—C9—O2 | 170.4 (3) | C7—C24—C25—C26 | 179.2 (3) |
C7—C8—C9—O2 | −10.1 (5) | C24—C25—C26—C27 | −0.7 (5) |
C13—C8—C9—C10 | −8.1 (5) | C25—C26—C27—C28 | 1.4 (5) |
C7—C8—C9—C10 | 171.5 (3) | C25—C26—C27—O3 | 180.0 (3) |
O2—C9—C10—C11 | 159.4 (3) | C30—O3—C27—C26 | −1.7 (5) |
C8—C9—C10—C11 | −22.2 (5) | C30—O3—C27—C28 | 177.0 (3) |
C9—C10—C11—C23 | 168.9 (3) | C26—C27—C28—C29 | −1.4 (6) |
C9—C10—C11—C12 | 50.2 (4) | O3—C27—C28—C29 | 179.9 (3) |
C9—C10—C11—C22 | −70.4 (4) | C27—C28—C29—C24 | 0.7 (6) |
C10—C11—C12—C13 | −51.3 (4) | C25—C24—C29—C28 | 0.0 (5) |
C23—C11—C12—C13 | −170.2 (3) | C7—C24—C29—C28 | −179.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O2i | 0.93 | 2.48 | 3.366 (4) | 161 |
C21—H21A···O2ii | 0.96 | 2.53 | 3.418 (4) | 154 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C30H32ClNO3 |
Mr | 490.02 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.227 (2), 10.883 (2), 20.178 (3) |
β (°) | 100.788 (2) |
V (Å3) | 2637.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.40 × 0.38 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.933, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10435, 4516, 2146 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.146, 1.02 |
No. of reflections | 4516 |
No. of parameters | 321 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.37 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O2i | 0.93 | 2.48 | 3.366 (4) | 161 |
C21—H21A···O2ii | 0.96 | 2.53 | 3.418 (4) | 154 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |
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 & Brychey, 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 report herein the structure of the title compound.
In the title molecule, the dihydropyridine ring is in a boat conformation, with atoms N1 and C7 deviating from the C1/C6/C8/C13 plane by 0.099 (5) and 0.255 (5) Å, respectively (Fig. 1). Both cyclohexene rings adopt envelope conformations: atom C3 deviaties from the C1/C2/C4/C5/C6 by 0.667 (5) Å and atom C11 deviates from the C8/C9/C10/C12/C13 plane by 0.660 (5) Å. The dihedral angle between the C1/C6/C8/C13 plane and the C14–C29 benzene ring attached at atom N1 is 81.31 (11)° and that between the C1/C6/C8/C13 plane and the C24–C29 benzene ring attached at atom C7 is 88.84 (12)°.
The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 1).