Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C30H32ClNO2, has been synthesized by the reaction of 4-chloro­benz­aldehyde, 5,5-di­methyl-1,3-cyclo­hexane­dione and p-toluidine in ethyl­ene glycol under microwave irradiation. X-ray analysis reveals that the 1,4-di­hydro­pyridine ring adopts a boat conformation, and the other two partially saturated six-membered rings adopt half-chair conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015125/ob6269sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015125/ob6269Isup2.hkl
Contains datablock I

CCDC reference: 221686

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.103
  • Data-to-parameter ratio = 15.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of . 43.00 A   3
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-10-(4-methylphenyl)- 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione top
Crystal data top
C30H32ClNO2F(000) = 1008
Mr = 474.02Dx = 1.182 Mg m3
Monoclinic, P21/nMelting point = 546–548 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 15.246 (2) ÅCell parameters from 29 reflections
b = 11.007 (2) Åθ = 2.8–12.9°
c = 16.244 (2) ŵ = 0.17 mm1
β = 102.31 (1)°T = 296 K
V = 2663.0 (7) Å3Block, colorless
Z = 40.44 × 0.36 × 0.36 mm
Data collection top
Siemens P4
diffractometer
2812 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω scansh = 018
Absorption correction: empirical (using intensity measurements)
(Sheldrick, 1990)
k = 013
Tmin = 0.948, Tmax = 0.965l = 1919
5509 measured reflections3 standard reflections every 97 reflections
4826 independent reflections intensity decay: 3.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.001
4826 reflectionsΔρmax = 0.16 e Å3
313 parametersΔρmin = 0.17 e Å3
2 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0113 (7)
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
xyzUiso*/Ueq
Cl0.23972 (4)0.07910 (6)0.68600 (5)0.0889 (3)
O10.39805 (9)0.31348 (13)0.45861 (8)0.0629 (4)
O20.64247 (10)0.16749 (13)0.69988 (10)0.0745 (5)
N0.49549 (10)0.54529 (13)0.70567 (9)0.0437 (4)
C10.31603 (14)0.03245 (18)0.67100 (13)0.0519 (5)
C20.38144 (13)0.00377 (18)0.62823 (13)0.0514 (5)
H20.38620.07480.60860.062*
C30.44025 (13)0.09334 (16)0.61457 (12)0.0459 (5)
H30.48500.07400.58580.055*
C40.43422 (12)0.21086 (16)0.64270 (11)0.0396 (4)
C50.36799 (13)0.23556 (18)0.68694 (13)0.0543 (5)
H50.36350.31360.70770.065*
C60.30846 (14)0.14732 (19)0.70107 (13)0.0603 (6)
H60.26410.16560.73050.072*
C70.44023 (11)0.52618 (16)0.62607 (11)0.0400 (4)
C80.38069 (13)0.63041 (17)0.58860 (12)0.0505 (5)
H8A0.41560.68690.56280.061*
H8B0.36070.67300.63350.061*
C90.29828 (12)0.59086 (18)0.52239 (12)0.0506 (5)
C100.33009 (13)0.50796 (18)0.45969 (12)0.0536 (5)
H10A0.27790.47330.42230.064*
H10B0.36190.55660.42570.064*
C110.39060 (12)0.40585 (17)0.49920 (12)0.0455 (5)
C120.44224 (12)0.41988 (16)0.58523 (11)0.0401 (4)
C130.49573 (11)0.31119 (16)0.62463 (11)0.0409 (5)
H130.52880.27970.58370.049*
C140.56404 (12)0.35044 (16)0.70189 (12)0.0432 (5)
C150.63746 (13)0.26624 (18)0.73359 (13)0.0544 (5)
C160.70995 (15)0.3067 (2)0.80658 (15)0.0775 (7)
H16A0.75700.34650.78470.093*
H16B0.73600.23550.83770.093*
C170.67782 (15)0.39221 (19)0.86650 (14)0.0700 (7)
C180.62946 (14)0.49787 (18)0.81610 (13)0.0597 (6)
H18A0.59950.54530.85230.072*
H18B0.67350.54990.79870.072*
C190.56108 (12)0.45936 (16)0.73897 (12)0.0431 (5)
C200.49738 (12)0.66324 (16)0.74550 (11)0.0417 (5)
C210.54892 (13)0.75520 (17)0.72305 (12)0.0459 (5)
H210.58150.74230.68150.055*
C220.55191 (13)0.86680 (17)0.76261 (13)0.0512 (5)
H220.58670.92870.74710.061*
C230.50440 (14)0.88828 (18)0.82464 (13)0.0530 (5)
C240.45328 (14)0.7950 (2)0.84581 (14)0.0623 (6)
H240.42070.80780.88730.075*
C250.44917 (14)0.68276 (18)0.80692 (13)0.0553 (5)
H250.41410.62100.82210.066*
C260.25253 (15)0.7033 (2)0.47719 (15)0.0758 (7)
H26A0.29390.74550.45030.091*
H26B0.23400.75610.51740.091*
H26C0.20090.67900.43550.091*
C270.23176 (13)0.5237 (2)0.56408 (14)0.0715 (7)
H27A0.17950.50240.52220.086*
H27B0.21460.57530.60560.086*
H27C0.25930.45130.59070.086*
C280.6150 (2)0.3269 (2)0.91255 (16)0.1047 (10)
H28A0.56400.29710.87240.126*
H28B0.59530.38230.95050.126*
H28C0.64600.26000.94380.126*
C290.75754 (19)0.4419 (2)0.93108 (18)0.1171 (12)
H29A0.73640.49790.96780.141*
H29B0.79780.48310.90240.141*
H29C0.78850.37610.96360.141*
C300.50754 (16)1.0124 (2)0.86466 (15)0.0814 (8)
H30A0.56631.04670.86930.098*
H30B0.49461.00520.91980.098*
H30C0.46371.06420.83040.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0909 (5)0.0653 (4)0.1169 (6)0.0289 (3)0.0367 (4)0.0107 (4)
O10.0758 (10)0.0610 (9)0.0496 (9)0.0083 (8)0.0082 (7)0.0149 (8)
O20.0648 (10)0.0538 (10)0.0973 (12)0.0149 (8)0.0002 (9)0.0215 (9)
N0.0435 (9)0.0360 (8)0.0458 (9)0.0010 (7)0.0035 (7)0.0059 (7)
C10.0535 (13)0.0459 (13)0.0544 (13)0.0098 (10)0.0075 (11)0.0074 (10)
C20.0577 (13)0.0359 (11)0.0549 (13)0.0023 (10)0.0009 (11)0.0034 (9)
C30.0457 (11)0.0406 (11)0.0500 (12)0.0007 (9)0.0066 (9)0.0061 (9)
C40.0401 (10)0.0375 (11)0.0388 (10)0.0016 (8)0.0031 (9)0.0036 (8)
C50.0631 (14)0.0416 (12)0.0634 (14)0.0039 (10)0.0255 (12)0.0090 (10)
C60.0624 (14)0.0540 (14)0.0713 (15)0.0064 (11)0.0291 (12)0.0014 (12)
C70.0363 (10)0.0392 (11)0.0424 (11)0.0053 (8)0.0035 (9)0.0003 (9)
C80.0481 (12)0.0482 (12)0.0501 (12)0.0002 (9)0.0010 (10)0.0015 (10)
C90.0425 (11)0.0553 (12)0.0486 (12)0.0042 (10)0.0026 (10)0.0012 (10)
C100.0530 (13)0.0599 (13)0.0428 (12)0.0122 (11)0.0007 (10)0.0009 (10)
C110.0473 (11)0.0452 (12)0.0447 (11)0.0157 (10)0.0109 (9)0.0036 (10)
C120.0390 (10)0.0386 (11)0.0419 (11)0.0090 (8)0.0067 (9)0.0033 (9)
C130.0396 (10)0.0393 (11)0.0450 (11)0.0024 (9)0.0116 (9)0.0062 (9)
C140.0390 (11)0.0391 (11)0.0499 (11)0.0042 (9)0.0059 (9)0.0039 (9)
C150.0493 (12)0.0429 (12)0.0677 (14)0.0014 (10)0.0047 (11)0.0037 (11)
C160.0657 (15)0.0578 (14)0.0929 (18)0.0137 (12)0.0193 (14)0.0069 (14)
C170.0808 (17)0.0462 (13)0.0658 (15)0.0036 (12)0.0230 (13)0.0016 (12)
C180.0587 (13)0.0436 (12)0.0646 (14)0.0002 (10)0.0143 (11)0.0054 (10)
C190.0391 (10)0.0388 (11)0.0479 (12)0.0027 (9)0.0011 (9)0.0005 (9)
C200.0413 (11)0.0377 (10)0.0411 (11)0.0020 (9)0.0023 (9)0.0040 (9)
C210.0453 (11)0.0457 (12)0.0445 (11)0.0012 (9)0.0048 (9)0.0036 (9)
C220.0513 (12)0.0405 (12)0.0567 (13)0.0013 (9)0.0003 (11)0.0025 (10)
C230.0511 (13)0.0473 (13)0.0533 (13)0.0084 (10)0.0051 (11)0.0113 (10)
C240.0631 (14)0.0678 (15)0.0580 (14)0.0065 (12)0.0177 (12)0.0171 (12)
C250.0561 (13)0.0515 (13)0.0589 (13)0.0039 (10)0.0137 (11)0.0038 (11)
C260.0678 (15)0.0751 (17)0.0711 (16)0.0143 (13)0.0149 (13)0.0023 (13)
C270.0471 (13)0.0966 (18)0.0684 (16)0.0043 (13)0.0068 (11)0.0002 (14)
C280.166 (3)0.0758 (19)0.0653 (17)0.002 (2)0.0096 (19)0.0042 (15)
C290.121 (2)0.0694 (17)0.117 (2)0.0190 (17)0.072 (2)0.0135 (16)
C300.0909 (18)0.0616 (15)0.0827 (18)0.0128 (14)0.0015 (15)0.0276 (13)
Geometric parameters (Å, º) top
Cl—C11.744 (2)C16—C171.509 (3)
O1—C111.230 (2)C16—H16A0.9700
O2—C151.227 (2)C16—H16B0.9700
N—C191.399 (2)C17—C281.516 (3)
N—C71.400 (2)C17—C181.520 (3)
N—C201.448 (2)C17—C291.528 (3)
C1—C21.368 (3)C18—C191.510 (2)
C1—C61.369 (3)C18—H18A0.9700
C2—C31.382 (3)C18—H18B0.9700
C2—H20.9300C20—C251.376 (3)
C3—C41.381 (2)C20—C211.377 (2)
C3—H30.9300C21—C221.382 (3)
C4—C51.385 (2)C21—H210.9300
C4—C131.517 (2)C22—C231.381 (3)
C5—C61.381 (3)C22—H220.9300
C5—H50.9300C23—C241.376 (3)
C6—H60.9300C23—C301.509 (3)
C7—C121.349 (2)C24—C251.383 (3)
C7—C81.508 (2)C24—H240.9300
C8—C91.533 (3)C25—H250.9300
C8—H8A0.9700C26—H26A0.9600
C8—H8B0.9700C26—H26B0.9600
C9—C101.522 (3)C26—H26C0.9600
C9—C271.525 (3)C27—H27A0.9600
C9—C261.530 (3)C27—H27B0.9600
C10—C111.508 (3)C27—H27C0.9600
C10—H10A0.9700C28—H28A0.9600
C10—H10B0.9700C28—H28B0.9600
C11—C121.459 (2)C28—H28C0.9600
C12—C131.511 (2)C29—H29A0.9600
C13—C141.513 (2)C29—H29B0.9600
C13—H130.9800C29—H29C0.9600
C14—C191.347 (2)C30—H30A0.9600
C14—C151.460 (3)C30—H30B0.9600
C15—C161.505 (3)C30—H30C0.9600
C19—N—C7119.69 (15)H16A—C16—H16B107.6
C19—N—C20119.27 (14)C16—C17—C28110.4 (2)
C7—N—C20119.86 (14)C16—C17—C18108.48 (19)
C2—C1—C6121.34 (19)C28—C17—C18110.1 (2)
C2—C1—Cl119.25 (16)C16—C17—C29110.3 (2)
C6—C1—Cl119.40 (17)C28—C17—C29109.0 (2)
C1—C2—C3119.01 (18)C18—C17—C29108.62 (18)
C1—C2—H2120.5C19—C18—C17113.71 (16)
C3—C2—H2120.5C19—C18—H18A108.8
C4—C3—C2121.58 (19)C17—C18—H18A108.8
C4—C3—H3119.2C19—C18—H18B108.8
C2—C3—H3119.2C17—C18—H18B108.8
C3—C4—C5117.55 (17)H18A—C18—H18B107.7
C3—C4—C13122.01 (17)C14—C19—N121.22 (16)
C5—C4—C13120.42 (16)C14—C19—C18122.55 (17)
C6—C5—C4121.70 (19)N—C19—C18116.19 (16)
C6—C5—H5119.1C25—C20—C21120.01 (18)
C4—C5—H5119.1C25—C20—N120.07 (17)
C1—C6—C5118.8 (2)C21—C20—N119.91 (17)
C1—C6—H6120.6C20—C21—C22119.60 (19)
C5—C6—H6120.6C20—C21—H21120.2
C12—C7—N120.81 (16)C22—C21—H21120.2
C12—C7—C8122.42 (16)C23—C22—C21121.4 (2)
N—C7—C8116.76 (15)C23—C22—H22119.3
C7—C8—C9113.58 (16)C21—C22—H22119.3
C7—C8—H8A108.9C24—C23—C22117.89 (19)
C9—C8—H8A108.9C24—C23—C30122.4 (2)
C7—C8—H8B108.9C22—C23—C30119.7 (2)
C9—C8—H8B108.9C23—C24—C25121.7 (2)
H8A—C8—H8B107.7C23—C24—H24119.2
C10—C9—C27110.11 (17)C25—C24—H24119.2
C10—C9—C26109.99 (17)C20—C25—C24119.4 (2)
C27—C9—C26109.08 (18)C20—C25—H25120.3
C10—C9—C8108.02 (16)C24—C25—H25120.3
C27—C9—C8110.44 (17)C9—C26—H26A109.5
C26—C9—C8109.19 (16)C9—C26—H26B109.5
C11—C10—C9114.55 (16)H26A—C26—H26B109.5
C11—C10—H10A108.6C9—C26—H26C109.5
C9—C10—H10A108.6H26A—C26—H26C109.5
C11—C10—H10B108.6H26B—C26—H26C109.5
C9—C10—H10B108.6C9—C27—H27A109.5
H10A—C10—H10B107.6C9—C27—H27B109.5
O1—C11—C12120.56 (18)H27A—C27—H27B109.5
O1—C11—C10120.39 (17)C9—C27—H27C109.5
C12—C11—C10119.02 (17)H27A—C27—H27C109.5
C7—C12—C11119.93 (17)H27B—C27—H27C109.5
C7—C12—C13123.05 (16)C17—C28—H28A109.5
C11—C12—C13117.02 (15)C17—C28—H28B109.5
C12—C13—C14109.83 (14)H28A—C28—H28B109.5
C12—C13—C4110.98 (14)C17—C28—H28C109.5
C14—C13—C4113.07 (15)H28A—C28—H28C109.5
C12—C13—H13107.6H28B—C28—H28C109.5
C14—C13—H13107.6C17—C29—H29A109.5
C4—C13—H13107.6C17—C29—H29B109.5
C19—C14—C15120.24 (17)H29A—C29—H29B109.5
C19—C14—C13122.85 (17)C17—C29—H29C109.5
C15—C14—C13116.86 (16)H29A—C29—H29C109.5
O2—C15—C14121.40 (19)H29B—C29—H29C109.5
O2—C15—C16120.56 (19)C23—C30—H30A109.5
C14—C15—C16117.97 (18)C23—C30—H30B109.5
C15—C16—C17114.06 (18)H30A—C30—H30B109.5
C15—C16—H16A108.7C23—C30—H30C109.5
C17—C16—H16A108.7H30A—C30—H30C109.5
C15—C16—H16B108.7H30B—C30—H30C109.5
C17—C16—H16B108.7
C6—C1—C2—C30.7 (3)C12—C13—C14—C1914.3 (2)
Cl—C1—C2—C3178.29 (14)C4—C13—C14—C19110.3 (2)
C1—C2—C3—C40.3 (3)C12—C13—C14—C15163.04 (16)
C2—C3—C4—C51.3 (3)C4—C13—C14—C1572.4 (2)
C2—C3—C4—C13177.18 (16)C19—C14—C15—O2178.6 (2)
C3—C4—C5—C61.5 (3)C13—C14—C15—O21.2 (3)
C13—C4—C5—C6177.07 (18)C19—C14—C15—C161.7 (3)
C2—C1—C6—C50.5 (3)C13—C14—C15—C16175.72 (18)
Cl—C1—C6—C5178.42 (16)O2—C15—C16—C17151.8 (2)
C4—C5—C6—C10.6 (3)C14—C15—C16—C1731.2 (3)
C19—N—C7—C127.7 (3)C15—C16—C17—C2867.4 (3)
C20—N—C7—C12175.19 (17)C15—C16—C17—C1853.3 (3)
C19—N—C7—C8171.17 (16)C15—C16—C17—C29172.1 (2)
C20—N—C7—C83.7 (2)C16—C17—C18—C1948.4 (3)
C12—C7—C8—C924.3 (3)C28—C17—C18—C1972.5 (2)
N—C7—C8—C9156.82 (16)C29—C17—C18—C19168.3 (2)
C7—C8—C9—C1050.0 (2)C15—C14—C19—N174.83 (17)
C7—C8—C9—C2770.4 (2)C13—C14—C19—N2.4 (3)
C7—C8—C9—C26169.62 (17)C15—C14—C19—C182.8 (3)
C27—C9—C10—C1170.3 (2)C13—C14—C19—C18179.96 (17)
C26—C9—C10—C11169.50 (16)C7—N—C19—C149.7 (3)
C8—C9—C10—C1150.4 (2)C20—N—C19—C14177.23 (18)
C9—C10—C11—O1157.17 (17)C7—N—C19—C18168.11 (17)
C9—C10—C11—C1224.8 (2)C20—N—C19—C180.5 (3)
N—C7—C12—C11174.18 (16)C17—C18—C19—C1422.0 (3)
C8—C7—C12—C114.6 (3)C17—C18—C19—N160.23 (19)
N—C7—C12—C136.3 (3)C19—N—C20—C2592.2 (2)
C8—C7—C12—C13174.89 (16)C7—N—C20—C25100.3 (2)
O1—C11—C12—C7173.47 (17)C19—N—C20—C2186.5 (2)
C10—C11—C12—C74.6 (3)C7—N—C20—C2181.0 (2)
O1—C11—C12—C137.0 (3)C25—C20—C21—C220.1 (3)
C10—C11—C12—C13174.94 (16)N—C20—C21—C22178.63 (16)
C7—C12—C13—C1416.3 (2)C20—C21—C22—C230.2 (3)
C11—C12—C13—C14164.21 (15)C21—C22—C23—C240.3 (3)
C7—C12—C13—C4109.50 (19)C21—C22—C23—C30178.40 (19)
C11—C12—C13—C470.0 (2)C22—C23—C24—C250.2 (3)
C3—C4—C13—C12127.26 (18)C30—C23—C24—C25178.2 (2)
C5—C4—C13—C1251.2 (2)C21—C20—C25—C240.2 (3)
C3—C4—C13—C14108.80 (19)N—C20—C25—C24178.49 (18)
C5—C4—C13—C1472.7 (2)C23—C24—C25—C200.1 (3)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds