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The title compound, C25H31NO4, was synthesized by the reaction of dimedone with 4-hydroxy-3-methoxy­benz­aldehyde and CH3NH2HCl(NaOAc) in glycol. X-ray analysis reveals that the dihydropyridine ring is in a distorted-boat conformation. O—H...O hydrogen bonds involving the hydroxy and carbonyl O atoms link glide-related mol­ecules into zigzag chains along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023621/ci6434sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023621/ci6434Isup2.hkl
Contains datablock I

CCDC reference: 253031

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.108
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C25 .. 6.83 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

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-Hydroxy-3-methyoxyphenyl)-3,3,6,6,10-pentamethyl-1,2,3,4,5,6,7,8,9,10- decahydroacridine-1,8-dione top
Crystal data top
C25H31NO4F(000) = 880
Mr = 409.51Dx = 1.263 Mg m3
Monoclinic, P21/cMelting point = 522–523 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.640 (2) ÅCell parameters from 41 reflections
b = 14.884 (2) Åθ = 3.7–15.2°
c = 13.604 (2) ŵ = 0.09 mm1
β = 91.15 (1)°T = 295 K
V = 2154.0 (6) Å3Block, yellow
Z = 40.58 × 0.30 × 0.22 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.015
Radiation source: normal-focus sealed tubeθmax = 25.3°, θmin = 1.9°
Graphite monochromatorh = 012
ω scansk = 017
4445 measured reflectionsl = 1616
3899 independent reflections3 standard reflections every 97 reflections
2409 reflections with I > 2σ(I) intensity decay: 3.4%
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0566P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
3899 reflectionsΔρmax = 0.18 e Å3
279 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0075 (9)
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
O10.36976 (13)0.43463 (10)0.02554 (10)0.0516 (4)
O20.73554 (12)0.38486 (10)0.23334 (11)0.0529 (4)
O30.22405 (13)0.15163 (10)0.39116 (11)0.0540 (4)
H3O0.27000.12350.42930.065*
O40.10489 (12)0.25260 (10)0.26167 (11)0.0556 (4)
N10.44284 (14)0.61237 (10)0.30682 (11)0.0329 (4)
C10.37393 (17)0.59243 (12)0.22204 (13)0.0312 (4)
C20.27655 (18)0.65910 (12)0.18813 (15)0.0419 (5)
H2A0.31890.71420.17010.050*
H2B0.22300.67280.24300.050*
C30.19330 (19)0.62924 (13)0.10138 (14)0.0426 (5)
C40.2742 (2)0.57990 (15)0.02757 (15)0.0535 (6)
H4A0.22030.55600.02450.064*
H4B0.33140.62240.00180.064*
C50.34902 (17)0.50441 (13)0.07256 (14)0.0375 (5)
C60.39888 (16)0.51602 (11)0.17121 (13)0.0311 (4)
C70.48269 (16)0.44461 (11)0.21507 (13)0.0310 (4)
H70.52470.41510.16030.037*
C80.58323 (16)0.49097 (12)0.27558 (13)0.0314 (4)
C90.71064 (18)0.45495 (13)0.27699 (14)0.0384 (5)
C100.81091 (19)0.50785 (15)0.33050 (16)0.0487 (6)
H10A0.84460.55230.28610.058*
H10B0.87890.46760.34950.058*
C110.76399 (18)0.55524 (14)0.42176 (15)0.0429 (5)
C120.65133 (18)0.61390 (13)0.39190 (15)0.0419 (5)
H12A0.60860.63240.45090.050*
H12B0.68210.66770.36010.050*
C130.55786 (17)0.56887 (12)0.32400 (13)0.0320 (4)
C140.41126 (16)0.37113 (11)0.27048 (13)0.0311 (4)
C150.46935 (18)0.31944 (12)0.34254 (14)0.0364 (5)
H150.55050.33380.36380.044*
C160.40834 (18)0.24606 (13)0.38403 (14)0.0392 (5)
H160.44990.21190.43180.047*
C170.28763 (17)0.22344 (12)0.35539 (14)0.0360 (5)
C180.22622 (17)0.27730 (13)0.28580 (14)0.0370 (5)
C190.28808 (17)0.34885 (12)0.24364 (14)0.0359 (5)
H190.24630.38310.19600.043*
C200.0326 (2)0.31353 (16)0.2042 (2)0.0705 (8)
H20A0.02960.37060.23700.085*
H20B0.05120.29060.19550.085*
H20C0.07030.32080.14120.085*
C210.0886 (2)0.56812 (15)0.1377 (2)0.0678 (7)
H21A0.04260.54390.08240.081*
H21B0.03290.60210.17800.081*
H21C0.12470.51990.17560.081*
C220.1343 (2)0.71285 (16)0.05335 (18)0.0707 (8)
H22A0.19960.75180.03070.085*
H22B0.08470.74410.10060.085*
H22C0.08160.69500.00130.085*
C230.8685 (2)0.61519 (17)0.46528 (18)0.0678 (7)
H23A0.93920.57860.48460.081*
H23B0.83780.64640.52170.081*
H23C0.89400.65800.41680.081*
C240.7253 (2)0.48726 (16)0.49951 (17)0.0588 (6)
H24A0.65460.45320.47530.071*
H24B0.70280.51840.55840.071*
H24C0.79430.44740.51370.071*
C250.4111 (2)0.69286 (13)0.36509 (16)0.0545 (6)
H25A0.46120.74270.34420.065*
H25B0.42790.68120.43350.065*
H25C0.32370.70690.35540.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0559 (9)0.0509 (9)0.0477 (9)0.0053 (8)0.0107 (7)0.0178 (7)
O20.0386 (8)0.0489 (9)0.0710 (10)0.0101 (7)0.0014 (7)0.0166 (8)
O30.0453 (9)0.0502 (9)0.0660 (11)0.0131 (8)0.0116 (7)0.0232 (8)
O40.0334 (8)0.0566 (9)0.0761 (11)0.0110 (7)0.0162 (7)0.0236 (8)
N10.0397 (9)0.0269 (8)0.0321 (8)0.0044 (7)0.0004 (7)0.0054 (7)
C10.0317 (10)0.0274 (10)0.0347 (10)0.0002 (8)0.0031 (8)0.0034 (8)
C20.0448 (12)0.0297 (11)0.0513 (13)0.0039 (9)0.0022 (10)0.0025 (10)
C30.0413 (12)0.0415 (12)0.0448 (12)0.0074 (10)0.0050 (10)0.0039 (10)
C40.0609 (15)0.0595 (14)0.0398 (12)0.0113 (12)0.0098 (11)0.0018 (11)
C50.0333 (11)0.0413 (12)0.0378 (11)0.0018 (9)0.0009 (9)0.0016 (10)
C60.0308 (10)0.0284 (10)0.0342 (11)0.0006 (8)0.0024 (8)0.0007 (9)
C70.0306 (10)0.0278 (10)0.0346 (10)0.0031 (8)0.0011 (8)0.0047 (8)
C80.0316 (10)0.0286 (10)0.0340 (11)0.0019 (8)0.0006 (8)0.0002 (8)
C90.0357 (11)0.0386 (12)0.0411 (12)0.0013 (10)0.0036 (9)0.0002 (10)
C100.0316 (11)0.0554 (14)0.0590 (14)0.0051 (10)0.0021 (10)0.0052 (11)
C110.0397 (12)0.0454 (12)0.0434 (12)0.0063 (10)0.0058 (10)0.0044 (10)
C120.0468 (12)0.0357 (11)0.0430 (12)0.0074 (10)0.0033 (10)0.0036 (10)
C130.0356 (11)0.0281 (10)0.0324 (10)0.0043 (8)0.0018 (9)0.0021 (8)
C140.0308 (10)0.0246 (10)0.0380 (11)0.0023 (8)0.0007 (8)0.0053 (8)
C150.0314 (10)0.0324 (10)0.0452 (12)0.0003 (9)0.0063 (9)0.0022 (9)
C160.0409 (11)0.0348 (11)0.0416 (12)0.0024 (10)0.0077 (9)0.0037 (9)
C170.0360 (11)0.0310 (10)0.0410 (11)0.0045 (9)0.0001 (9)0.0022 (9)
C180.0294 (10)0.0374 (11)0.0440 (12)0.0024 (9)0.0034 (9)0.0024 (9)
C190.0335 (11)0.0317 (11)0.0423 (12)0.0012 (9)0.0061 (9)0.0039 (9)
C200.0383 (13)0.0743 (17)0.098 (2)0.0064 (13)0.0209 (13)0.0292 (16)
C210.0409 (13)0.0595 (16)0.103 (2)0.0003 (12)0.0043 (13)0.0032 (15)
C220.0757 (18)0.0701 (17)0.0657 (16)0.0295 (15)0.0114 (14)0.0135 (14)
C230.0562 (15)0.0732 (17)0.0733 (18)0.0118 (13)0.0162 (13)0.0177 (14)
C240.0635 (16)0.0617 (15)0.0507 (14)0.0036 (13)0.0074 (12)0.0065 (12)
C250.0710 (15)0.0426 (13)0.0497 (13)0.0133 (12)0.0009 (12)0.0088 (11)
Geometric parameters (Å, º) top
O1—C51.242 (2)C11—C121.531 (3)
O2—C91.232 (2)C11—C231.535 (3)
O3—C171.360 (2)C12—C131.501 (2)
O3—H3O0.82C12—H12A0.97
O4—C181.376 (2)C12—H12B0.97
O4—C201.415 (2)C14—C151.382 (2)
N1—C11.386 (2)C14—C191.394 (2)
N1—C131.400 (2)C15—C161.395 (3)
N1—C251.479 (2)C15—H150.93
C1—C61.360 (2)C16—C171.376 (3)
C1—C21.501 (2)C16—H160.93
C2—C31.527 (3)C17—C181.393 (3)
C2—H2A0.97C18—C191.383 (3)
C2—H2B0.97C19—H190.93
C3—C41.524 (3)C20—H20A0.96
C3—C211.528 (3)C20—H20B0.96
C3—C221.534 (3)C20—H20C0.96
C4—C51.500 (3)C21—H21A0.96
C4—H4A0.97C21—H21B0.96
C4—H4B0.97C21—H21C0.96
C5—C61.444 (3)C22—H22A0.96
C6—C71.503 (2)C22—H22B0.96
C7—C81.504 (2)C22—H22C0.96
C7—C141.538 (2)C23—H23A0.96
C7—H70.98C23—H23B0.96
C8—C131.363 (2)C23—H23C0.96
C8—C91.458 (3)C24—H24A0.96
C9—C101.502 (3)C24—H24B0.96
C10—C111.521 (3)C24—H24C0.96
C10—H10A0.97C25—H25A0.96
C10—H10B0.97C25—H25B0.96
C11—C241.526 (3)C25—H25C0.96
C17—O3—H3O109.5C11—C12—H12B108.6
C18—O4—C20117.25 (16)H12A—C12—H12B107.6
C1—N1—C13119.07 (14)C8—C13—N1119.57 (16)
C1—N1—C25119.77 (16)C8—C13—C12122.81 (17)
C13—N1—C25119.55 (16)N1—C13—C12117.53 (15)
C6—C1—N1119.78 (16)C15—C14—C19117.27 (17)
C6—C1—C2122.50 (17)C15—C14—C7121.68 (16)
N1—C1—C2117.68 (15)C19—C14—C7120.81 (16)
C1—C2—C3115.55 (16)C14—C15—C16121.16 (17)
C1—C2—H2A108.4C14—C15—H15119.4
C3—C2—H2A108.4C16—C15—H15119.4
C1—C2—H2B108.4C17—C16—C15121.06 (18)
C3—C2—H2B108.4C17—C16—H16119.5
H2A—C2—H2B107.5C15—C16—H16119.5
C4—C3—C2108.84 (16)O3—C17—C16123.97 (18)
C4—C3—C21110.56 (18)O3—C17—C18117.74 (17)
C2—C3—C21109.77 (18)C16—C17—C18118.29 (17)
C4—C3—C22110.00 (18)O4—C18—C19124.00 (17)
C2—C3—C22108.61 (17)O4—C18—C17115.69 (17)
C21—C3—C22109.04 (18)C19—C18—C17120.29 (17)
C5—C4—C3113.21 (17)C18—C19—C14121.84 (17)
C5—C4—H4A108.9C18—C19—H19119.1
C3—C4—H4A108.9C14—C19—H19119.1
C5—C4—H4B108.9O4—C20—H20A109.5
C3—C4—H4B108.9O4—C20—H20B109.5
H4A—C4—H4B107.7H20A—C20—H20B109.5
O1—C5—C6120.87 (17)O4—C20—H20C109.5
O1—C5—C4120.97 (18)H20A—C20—H20C109.5
C6—C5—C4118.15 (17)H20B—C20—H20C109.5
C1—C6—C5120.06 (17)C3—C21—H21A109.5
C1—C6—C7120.65 (16)C3—C21—H21B109.5
C5—C6—C7119.24 (16)H21A—C21—H21B109.5
C6—C7—C8107.61 (14)C3—C21—H21C109.5
C6—C7—C14113.72 (14)H21A—C21—H21C109.5
C8—C7—C14114.27 (15)H21B—C21—H21C109.5
C6—C7—H7106.9C3—C22—H22A109.5
C8—C7—H7106.9C3—C22—H22B109.5
C14—C7—H7106.9H22A—C22—H22B109.5
C13—C8—C9119.97 (17)C3—C22—H22C109.5
C13—C8—C7120.61 (16)H22A—C22—H22C109.5
C9—C8—C7119.30 (16)H22B—C22—H22C109.5
O2—C9—C8120.94 (18)C11—C23—H23A109.5
O2—C9—C10121.33 (18)C11—C23—H23B109.5
C8—C9—C10117.70 (17)H23A—C23—H23B109.5
C9—C10—C11113.40 (17)C11—C23—H23C109.5
C9—C10—H10A108.9H23A—C23—H23C109.5
C11—C10—H10A108.9H23B—C23—H23C109.5
C9—C10—H10B108.9C11—C24—H24A109.5
C11—C10—H10B108.9C11—C24—H24B109.5
H10A—C10—H10B107.7H24A—C24—H24B109.5
C10—C11—C24110.83 (17)C11—C24—H24C109.5
C10—C11—C12108.42 (16)H24A—C24—H24C109.5
C24—C11—C12109.97 (17)H24B—C24—H24C109.5
C10—C11—C23109.71 (18)N1—C25—H25A109.5
C24—C11—C23108.73 (18)N1—C25—H25B109.5
C12—C11—C23109.16 (17)H25A—C25—H25B109.5
C13—C12—C11114.46 (16)N1—C25—H25C109.5
C13—C12—H12A108.6H25A—C25—H25C109.5
C11—C12—H12A108.6H25B—C25—H25C109.5
C13—C12—H12B108.6
C13—N1—C1—C617.9 (2)C9—C10—C11—C2465.8 (2)
C25—N1—C1—C6176.65 (17)C9—C10—C11—C1255.0 (2)
C13—N1—C1—C2159.99 (16)C9—C10—C11—C23174.10 (18)
C25—N1—C1—C25.5 (2)C10—C11—C12—C1344.5 (2)
C6—C1—C2—C38.9 (3)C24—C11—C12—C1376.8 (2)
N1—C1—C2—C3173.35 (16)C23—C11—C12—C13163.98 (17)
C1—C2—C3—C440.3 (2)C9—C8—C13—N1167.45 (16)
C1—C2—C3—C2180.8 (2)C7—C8—C13—N18.6 (3)
C1—C2—C3—C22160.09 (18)C9—C8—C13—C129.1 (3)
C2—C3—C4—C553.3 (2)C7—C8—C13—C12174.86 (16)
C21—C3—C4—C567.3 (2)C1—N1—C13—C819.3 (2)
C22—C3—C4—C5172.23 (18)C25—N1—C13—C8175.16 (17)
C3—C4—C5—O1145.32 (19)C1—N1—C13—C12157.39 (16)
C3—C4—C5—C636.2 (3)C25—N1—C13—C128.1 (2)
N1—C1—C6—C5165.92 (16)C11—C12—C13—C813.9 (3)
C2—C1—C6—C511.8 (3)C11—C12—C13—N1169.49 (16)
N1—C1—C6—C711.5 (3)C6—C7—C14—C15156.98 (16)
C2—C1—C6—C7170.75 (16)C8—C7—C14—C1532.9 (2)
O1—C5—C6—C1179.20 (18)C6—C7—C14—C1928.8 (2)
C4—C5—C6—C12.3 (3)C8—C7—C14—C19152.87 (16)
O1—C5—C6—C73.3 (3)C19—C14—C15—C162.2 (3)
C4—C5—C6—C7175.18 (17)C7—C14—C15—C16172.25 (16)
C1—C6—C7—C834.9 (2)C14—C15—C16—C170.8 (3)
C5—C6—C7—C8142.51 (16)C15—C16—C17—O3178.38 (18)
C1—C6—C7—C1492.7 (2)C15—C16—C17—C181.9 (3)
C5—C6—C7—C1489.9 (2)C20—O4—C18—C1912.0 (3)
C6—C7—C8—C1333.4 (2)C20—O4—C18—C17169.7 (2)
C14—C7—C8—C1394.0 (2)O3—C17—C18—O41.2 (3)
C6—C7—C8—C9142.73 (17)C16—C17—C18—O4178.60 (17)
C14—C7—C8—C990.0 (2)O3—C17—C18—C19177.14 (18)
C13—C8—C9—O2179.69 (18)C16—C17—C18—C193.1 (3)
C7—C8—C9—O23.6 (3)O4—C18—C19—C14179.89 (18)
C13—C8—C9—C101.7 (3)C17—C18—C19—C141.7 (3)
C7—C8—C9—C10174.38 (17)C15—C14—C19—C180.9 (3)
O2—C9—C10—C11147.0 (2)C7—C14—C19—C18173.55 (16)
C8—C9—C10—C1135.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O1i0.821.882.698 (2)175
Symmetry code: (i) x, y+1/2, z+1/2.
 

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