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The title compound, C25H28ClNO4, was synthesized by the reaction of dimedone with 4-chloro­benzaldehyde and glycine in glycol under microwave irradition. X-ray analysis reveals that the dihydro­pyridine ring is in a boat conformation and both cyclo­hexenone rings adopt envelope conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032903/ci6665sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032903/ci6665Isup2.hkl
Contains datablock I

CCDC reference: 290004

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.077
  • wR factor = 0.175
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT410_ALERT_2_C Short Intra H...H Contact H13B .. H20B .. 1.94 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10- decahydroacridine-10-acetic acid top
Crystal data top
C25H28ClNO4F(000) = 936
Mr = 441.93Dx = 1.277 Mg m3
Monoclinic, P21/cMelting point = 563–564 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71070 Å
a = 12.655 (3) ÅCell parameters from 5995 reflections
b = 16.582 (3) Åθ = 3.1–25.3°
c = 11.500 (3) ŵ = 0.20 mm1
β = 107.708 (6)°T = 193 K
V = 2298.9 (9) Å3Block, light yellow
Z = 40.25 × 0.18 × 0.15 mm
Data collection top
Rigaku MERCURY CCD area-detector
diffractometer
4190 independent reflections
Radiation source: fine-focus sealed tube2642 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.1°
ω scansh = 1415
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1919
Tmin = 0.952, Tmax = 0.971l = 1213
11302 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.99P]
where P = (Fo2 + 2Fc2)/3
4190 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
Cl10.15015 (12)0.58195 (8)0.33536 (13)0.0791 (5)
O10.4848 (2)0.37008 (16)0.8556 (2)0.0425 (7)
O20.1038 (2)0.31521 (16)0.8107 (2)0.0436 (7)
O30.3528 (2)0.01195 (17)0.6922 (3)0.0548 (8)
O40.3655 (2)0.03496 (15)0.5146 (2)0.0429 (7)
H40.40360.07160.55820.064*
N10.2973 (2)0.16477 (17)0.5914 (3)0.0305 (7)
C10.3940 (3)0.2051 (2)0.6531 (3)0.0308 (8)
C20.3897 (3)0.2738 (2)0.7153 (3)0.0314 (8)
C30.2803 (3)0.3132 (2)0.7075 (3)0.0307 (8)
H30.28760.33850.78860.037*
C40.1938 (3)0.2481 (2)0.6872 (3)0.0293 (8)
C50.1996 (3)0.1810 (2)0.6225 (3)0.0283 (8)
C60.4898 (3)0.3119 (2)0.7890 (3)0.0366 (9)
C70.5989 (3)0.2819 (3)0.7825 (4)0.0484 (11)
H7A0.65690.29540.85970.058*
H7B0.61750.31010.71540.058*
C80.6002 (3)0.1920 (2)0.7615 (4)0.0430 (10)
C90.5031 (3)0.1704 (2)0.6488 (3)0.0382 (9)
H9A0.51910.19060.57490.046*
H9B0.49650.11090.64220.046*
C100.1068 (3)0.2561 (2)0.7469 (3)0.0330 (8)
C110.0256 (3)0.1884 (2)0.7326 (3)0.0374 (9)
H11A0.04380.20950.74390.045*
H11B0.05640.14770.79700.045*
C120.0012 (3)0.1477 (2)0.6072 (3)0.0374 (9)
C130.1086 (3)0.1196 (2)0.5869 (3)0.0327 (8)
H13A0.13400.06980.63480.039*
H13B0.09400.10610.49960.039*
C140.2487 (3)0.3798 (2)0.6112 (3)0.0340 (9)
C150.2899 (3)0.3836 (2)0.5132 (4)0.0462 (10)
H150.33940.34280.50360.055*
C160.2608 (4)0.4456 (3)0.4283 (4)0.0547 (11)
H160.29120.44770.36230.066*
C170.1880 (4)0.5035 (2)0.4404 (4)0.0496 (11)
C180.1454 (4)0.5011 (3)0.5373 (5)0.0573 (12)
H180.09560.54180.54630.069*
C190.1752 (3)0.4394 (2)0.6209 (4)0.0508 (11)
H190.14460.43760.68670.061*
C200.3027 (3)0.09579 (19)0.5146 (3)0.0290 (8)
H20A0.35360.10880.46670.035*
H20B0.22810.08630.45630.035*
C210.3414 (3)0.0205 (2)0.5854 (3)0.0347 (9)
C220.7087 (3)0.1665 (3)0.7386 (5)0.0626 (13)
H22A0.71650.19530.66720.094*
H22B0.70750.10830.72370.094*
H22C0.77150.17980.81030.094*
C230.5901 (4)0.1457 (3)0.8735 (4)0.0617 (13)
H23A0.65180.16050.94540.093*
H23B0.59220.08760.85900.093*
H23C0.51970.15960.88770.093*
C240.0612 (3)0.2068 (2)0.5075 (4)0.0459 (10)
H24A0.13190.22250.51930.069*
H24B0.07530.18100.42750.069*
H24C0.01500.25470.51140.069*
C250.0738 (3)0.0734 (3)0.6021 (4)0.0544 (12)
H25A0.14530.09000.61100.082*
H25B0.03670.03650.66860.082*
H25C0.08610.04610.52360.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0932 (10)0.0538 (7)0.0720 (9)0.0071 (7)0.0020 (8)0.0169 (7)
O10.0342 (15)0.0469 (16)0.0480 (17)0.0103 (12)0.0148 (13)0.0148 (13)
O20.0370 (15)0.0515 (17)0.0471 (17)0.0050 (13)0.0199 (13)0.0191 (14)
O30.073 (2)0.0565 (19)0.0411 (18)0.0167 (16)0.0271 (16)0.0105 (14)
O40.0437 (16)0.0389 (15)0.0433 (16)0.0147 (12)0.0089 (14)0.0003 (12)
N10.0220 (15)0.0354 (16)0.0366 (17)0.0010 (13)0.0127 (14)0.0062 (14)
C10.0227 (18)0.040 (2)0.030 (2)0.0017 (16)0.0083 (16)0.0031 (17)
C20.0235 (18)0.041 (2)0.029 (2)0.0012 (16)0.0074 (16)0.0008 (17)
C30.0247 (18)0.036 (2)0.031 (2)0.0017 (15)0.0096 (16)0.0075 (16)
C40.0236 (18)0.0352 (19)0.0279 (19)0.0038 (15)0.0058 (16)0.0049 (16)
C50.0221 (17)0.0344 (19)0.0276 (19)0.0017 (15)0.0061 (15)0.0024 (16)
C60.028 (2)0.045 (2)0.035 (2)0.0022 (17)0.0081 (18)0.0029 (19)
C70.0211 (19)0.067 (3)0.052 (3)0.0043 (19)0.0046 (19)0.017 (2)
C80.0217 (19)0.059 (3)0.045 (2)0.0091 (18)0.0060 (18)0.009 (2)
C90.0242 (19)0.049 (2)0.041 (2)0.0020 (17)0.0083 (18)0.0085 (18)
C100.0251 (18)0.038 (2)0.035 (2)0.0008 (16)0.0073 (17)0.0042 (18)
C110.0291 (19)0.045 (2)0.043 (2)0.0041 (17)0.0184 (18)0.0067 (18)
C120.0243 (19)0.046 (2)0.043 (2)0.0066 (17)0.0123 (19)0.0090 (19)
C130.0266 (19)0.0321 (19)0.042 (2)0.0016 (16)0.0141 (18)0.0022 (17)
C140.0257 (19)0.034 (2)0.041 (2)0.0070 (16)0.0091 (17)0.0071 (17)
C150.054 (3)0.039 (2)0.049 (3)0.008 (2)0.020 (2)0.000 (2)
C160.066 (3)0.048 (3)0.050 (3)0.003 (2)0.017 (2)0.007 (2)
C170.049 (3)0.037 (2)0.052 (3)0.000 (2)0.001 (2)0.003 (2)
C180.042 (2)0.041 (2)0.085 (4)0.012 (2)0.015 (3)0.002 (3)
C190.042 (2)0.044 (2)0.071 (3)0.003 (2)0.025 (2)0.004 (2)
C200.0236 (17)0.036 (2)0.0278 (19)0.0028 (15)0.0087 (16)0.0047 (16)
C210.0283 (19)0.040 (2)0.037 (2)0.0030 (16)0.0121 (18)0.0015 (18)
C220.023 (2)0.079 (3)0.078 (3)0.004 (2)0.004 (2)0.025 (3)
C230.049 (3)0.073 (3)0.054 (3)0.016 (2)0.001 (2)0.004 (3)
C240.030 (2)0.058 (3)0.047 (3)0.0065 (19)0.007 (2)0.012 (2)
C250.036 (2)0.056 (3)0.078 (3)0.011 (2)0.028 (2)0.019 (2)
Geometric parameters (Å, º) top
Cl1—C171.740 (4)C11—H11B0.99
O1—C61.245 (4)C12—C241.524 (5)
O2—C101.232 (4)C12—C251.527 (5)
O3—C211.201 (4)C12—C131.549 (4)
O4—C211.324 (4)C13—H13A0.99
O4—H40.84C13—H13B0.99
N1—C11.386 (4)C14—C151.380 (5)
N1—C51.413 (4)C14—C191.384 (5)
N1—C201.459 (4)C15—C161.388 (6)
C1—C21.355 (5)C15—H150.95
C1—C91.510 (4)C16—C171.366 (6)
C2—C61.439 (5)C16—H160.95
C2—C31.509 (4)C17—C181.379 (6)
C3—C41.503 (5)C18—C191.375 (6)
C3—C141.528 (5)C18—H180.95
C3—H31.00C19—H190.95
C4—C51.353 (5)C20—C211.489 (5)
C4—C101.471 (4)C20—H20A0.99
C5—C131.498 (5)C20—H20B0.99
C6—C71.490 (5)C22—H22A0.98
C7—C81.511 (6)C22—H22B0.98
C7—H7A0.99C22—H22C0.98
C7—H7B0.99C23—H23A0.98
C8—C91.533 (5)C23—H23B0.98
C8—C221.534 (5)C23—H23C0.98
C8—C231.538 (6)C24—H24A0.98
C9—H9A0.99C24—H24B0.98
C9—H9B0.99C24—H24C0.98
C10—C111.496 (5)C25—H25A0.98
C11—C121.534 (5)C25—H25B0.98
C11—H11A0.99C25—H25C0.98
C21—O4—H4109.5C5—C13—C12113.9 (3)
C1—N1—C5118.9 (3)C5—C13—H13A108.8
C1—N1—C20119.4 (3)C12—C13—H13A108.8
C5—N1—C20120.6 (3)C5—C13—H13B108.8
C2—C1—N1120.3 (3)C12—C13—H13B108.8
C2—C1—C9121.5 (3)H13A—C13—H13B107.7
N1—C1—C9118.3 (3)C15—C14—C19117.6 (4)
C1—C2—C6120.7 (3)C15—C14—C3123.0 (3)
C1—C2—C3121.1 (3)C19—C14—C3119.5 (3)
C6—C2—C3118.2 (3)C14—C15—C16121.5 (4)
C4—C3—C2108.0 (3)C14—C15—H15119.3
C4—C3—C14112.8 (3)C16—C15—H15119.3
C2—C3—C14112.9 (3)C17—C16—C15119.5 (4)
C4—C3—H3107.6C17—C16—H16120.3
C2—C3—H3107.6C15—C16—H16120.3
C14—C3—H3107.6C16—C17—C18120.2 (4)
C5—C4—C10120.2 (3)C16—C17—Cl1120.5 (3)
C5—C4—C3121.2 (3)C18—C17—Cl1119.3 (3)
C10—C4—C3118.4 (3)C19—C18—C17119.7 (4)
C4—C5—N1119.6 (3)C19—C18—H18120.2
C4—C5—C13122.9 (3)C17—C18—H18120.2
N1—C5—C13117.4 (3)C18—C19—C14121.5 (4)
O1—C6—C2120.1 (3)C18—C19—H19119.2
O1—C6—C7120.7 (3)C14—C19—H19119.2
C2—C6—C7119.1 (3)N1—C20—C21113.2 (3)
C6—C7—C8113.1 (3)N1—C20—H20A108.9
C6—C7—H7A109.0C21—C20—H20A108.9
C8—C7—H7A109.0N1—C20—H20B108.9
C6—C7—H7B109.0C21—C20—H20B108.9
C8—C7—H7B109.0H20A—C20—H20B107.7
H7A—C7—H7B107.8O3—C21—O4124.6 (4)
C7—C8—C9108.7 (3)O3—C21—C20125.1 (3)
C7—C8—C22110.7 (3)O4—C21—C20110.2 (3)
C9—C8—C22108.7 (3)C8—C22—H22A109.5
C7—C8—C23110.5 (3)C8—C22—H22B109.5
C9—C8—C23110.0 (3)H22A—C22—H22B109.5
C22—C8—C23108.3 (3)C8—C22—H22C109.5
C1—C9—C8112.9 (3)H22A—C22—H22C109.5
C1—C9—H9A109.0H22B—C22—H22C109.5
C8—C9—H9A109.0C8—C23—H23A109.5
C1—C9—H9B109.0C8—C23—H23B109.5
C8—C9—H9B109.0H23A—C23—H23B109.5
H9A—C9—H9B107.8C8—C23—H23C109.5
O2—C10—C4120.8 (3)H23A—C23—H23C109.5
O2—C10—C11121.2 (3)H23B—C23—H23C109.5
C4—C10—C11117.9 (3)C12—C24—H24A109.5
C10—C11—C12112.4 (3)C12—C24—H24B109.5
C10—C11—H11A109.1H24A—C24—H24B109.5
C12—C11—H11A109.1C12—C24—H24C109.5
C10—C11—H11B109.1H24A—C24—H24C109.5
C12—C11—H11B109.1H24B—C24—H24C109.5
H11A—C11—H11B107.8C12—C25—H25A109.5
C24—C12—C25109.5 (3)C12—C25—H25B109.5
C24—C12—C11110.0 (3)H25A—C25—H25B109.5
C25—C12—C11110.5 (3)C12—C25—H25C109.5
C24—C12—C13110.1 (3)H25A—C25—H25C109.5
C25—C12—C13108.0 (3)H25B—C25—H25C109.5
C11—C12—C13108.8 (3)
C5—N1—C1—C218.6 (5)C7—C8—C9—C150.0 (4)
C20—N1—C1—C2173.6 (3)C22—C8—C9—C1170.5 (3)
C5—N1—C1—C9161.3 (3)C23—C8—C9—C171.2 (4)
C20—N1—C1—C96.4 (5)C5—C4—C10—O2176.7 (3)
N1—C1—C2—C6174.1 (3)C3—C4—C10—O21.1 (5)
C9—C1—C2—C65.9 (5)C5—C4—C10—C110.6 (5)
N1—C1—C2—C37.0 (5)C3—C4—C10—C11176.1 (3)
C9—C1—C2—C3173.0 (3)O2—C10—C11—C12148.5 (3)
C1—C2—C3—C430.6 (4)C4—C10—C11—C1234.3 (5)
C6—C2—C3—C4150.5 (3)C10—C11—C12—C2465.4 (4)
C1—C2—C3—C1494.9 (4)C10—C11—C12—C25173.6 (3)
C6—C2—C3—C1484.0 (4)C10—C11—C12—C1355.3 (4)
C2—C3—C4—C532.5 (4)C4—C5—C13—C1211.7 (5)
C14—C3—C4—C593.0 (4)N1—C5—C13—C12171.5 (3)
C2—C3—C4—C10143.0 (3)C24—C12—C13—C576.2 (4)
C14—C3—C4—C1091.5 (4)C25—C12—C13—C5164.3 (3)
C10—C4—C5—N1164.4 (3)C11—C12—C13—C544.4 (4)
C3—C4—C5—N111.0 (5)C4—C3—C14—C1599.8 (4)
C10—C4—C5—C1312.3 (5)C2—C3—C14—C1523.0 (5)
C3—C4—C5—C13172.3 (3)C4—C3—C14—C1979.9 (4)
C1—N1—C5—C416.7 (5)C2—C3—C14—C19157.3 (3)
C20—N1—C5—C4175.7 (3)C19—C14—C15—C161.2 (6)
C1—N1—C5—C13160.2 (3)C3—C14—C15—C16179.0 (4)
C20—N1—C5—C137.4 (5)C14—C15—C16—C171.2 (7)
C1—C2—C6—O1172.5 (3)C15—C16—C17—C181.1 (7)
C3—C2—C6—O18.5 (5)C15—C16—C17—Cl1180.0 (3)
C1—C2—C6—C78.6 (5)C16—C17—C18—C190.9 (7)
C3—C2—C6—C7170.3 (3)Cl1—C17—C18—C19179.8 (3)
O1—C6—C7—C8147.5 (4)C17—C18—C19—C140.9 (7)
C2—C6—C7—C833.7 (5)C15—C14—C19—C181.0 (6)
C6—C7—C8—C953.1 (4)C3—C14—C19—C18179.2 (4)
C6—C7—C8—C22172.4 (4)C1—N1—C20—C2178.4 (4)
C6—C7—C8—C2367.7 (4)C5—N1—C20—C2189.2 (4)
C2—C1—C9—C827.7 (5)N1—C20—C21—O310.1 (5)
N1—C1—C9—C8152.2 (3)N1—C20—C21—O4167.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.841.752.565 (4)163
C13—H13B···O2ii0.992.573.339 (4)134
C16—H16···O3ii0.952.413.339 (5)166
C20—H20A···O1ii0.992.413.397 (4)175
C20—H20B···O2ii0.992.523.229 (4)128
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y+1/2, z1/2.
 

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