9-[4-(1,2,3,4,5,6,7,8,9,10-Deca­hydro-3,3,6,6-tetra­methyl-1,8-dioxoacridin-9-yl)­phenyl]-1,2,3,4,5,6,7,8,9,10-deca­hydro-3,3,6,6-tetra­methyl­acridine-1,8-dione dihydrate

The title compound, C₄₀H₄₈N₂O₄·2H₂O, was synthesized by the reaction of dimedone with terephthal­aldehyde and NH₄OAc in glycol. X-ray analysis reveals that the di­hydro­pyridine and cyclo­hexenone rings adopt half-boat conformations. The screw-related mol­ecules form N—H...N and O—H...O hydrogen-bonded chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.160
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.65
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C17     ..       5.01 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         C6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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-(1,2,3,4,5,6,7,8,9,10-Decahydro-3,3,6,6-tetramethyl-1,8-dioxoacridin- 9-yl)phenyl]-1,2,3,4,5,6,7,8,9,10-decahydro-3,3,6,6-tetramethylacridine- 1,8-dione dihydrate

Crystal data

C40H48N2O4·2H2O	Dx = 1.170 Mg m^−3
Mr = 656.84	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 33 reflections
Hall symbol: -P 4bc	θ = 3.2–11.0°
a = 16.334 (2) Å	µ = 0.08 mm^−1
c = 13.975 (2) Å	T = 294 K
V = 3728.5 (8) Å^3	Prism, colourless
Z = 4	0.40 × 0.40 × 0.36 mm
F(000) = 1416

Data collection

Siemens P4 diffractometer	Rint = 0.041
Radiation source: normal-focus sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = 0→19
ω scans	k = 0→19
4104 measured reflections	l = −1→16
3296 independent reflections	3 standard reflections every 97 reflections
1412 reflections with I > 2σ(I)	intensity decay: 2.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2) + (0.0816P)^2] where P = (Fo^2 + 2Fc^2)/3
3296 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.41 e Å^−3
6 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.98071 (15)	0.19059 (15)	0.37361 (16)	0.0680 (7)
O2	0.82707 (16)	0.47223 (15)	0.37673 (17)	0.0720 (8)
N1	0.96109 (15)	0.36523 (15)	0.10665 (17)	0.0434 (7)
H1N	0.9690	0.3703	0.0461	0.052*
C1	0.78687 (18)	0.2697 (2)	0.2156 (2)	0.0510 (9)
H1	0.8116	0.2829	0.1576	0.061*
C2	0.82533 (18)	0.29042 (18)	0.3004 (2)	0.0395 (8)
C3	0.78729 (18)	0.26970 (19)	0.38558 (19)	0.0471 (8)
H3	0.8124	0.2825	0.4434	0.057*
C4	0.99006 (17)	0.29589 (19)	0.1521 (2)	0.0403 (8)
C5	1.0423 (2)	0.2418 (2)	0.0939 (2)	0.0520 (9)
H5A	1.0970	0.2646	0.0912	0.062*
H5B	1.0210	0.2402	0.0291	0.062*
C6	1.0473 (2)	0.1548 (2)	0.1321 (3)	0.0658 (11)
C7	1.0639 (2)	0.1587 (2)	0.2392 (3)	0.0723 (12)
H7A	1.0630	0.1036	0.2652	0.087*
H7B	1.1181	0.1811	0.2497	0.087*
C8	1.0022 (2)	0.2103 (2)	0.2921 (2)	0.0551 (9)
C9	0.97015 (17)	0.28252 (19)	0.2449 (2)	0.0419 (8)
C10	0.90774 (17)	0.33456 (18)	0.2969 (2)	0.0410 (8)
H10	0.9268	0.3440	0.3625	0.049*
C11	0.89870 (17)	0.41590 (18)	0.2474 (2)	0.0413 (8)
C12	0.8555 (2)	0.4815 (2)	0.2954 (2)	0.0528 (9)
C13	0.8433 (2)	0.5619 (2)	0.2436 (2)	0.0610 (10)
H13A	0.8910	0.5963	0.2535	0.073*
H13B	0.7963	0.5900	0.2705	0.073*
C14	0.8299 (2)	0.5500 (2)	0.1358 (2)	0.0523 (9)
C15	0.90164 (19)	0.50125 (19)	0.0971 (2)	0.0487 (9)
H15A	0.8898	0.4853	0.0317	0.058*
H15B	0.9498	0.5360	0.0960	0.058*
C16	0.92027 (18)	0.42620 (19)	0.1541 (2)	0.0400 (8)
C17	0.9667 (3)	0.1095 (2)	0.1141 (3)	0.0994 (16)
H17A	0.9710	0.0545	0.1378	0.119*
H17B	0.9556	0.1084	0.0467	0.119*
H17C	0.9230	0.1373	0.1466	0.119*
C18	1.1154 (3)	0.1098 (3)	0.0788 (3)	0.122 (2)
H18A	1.1668	0.1367	0.0904	0.147*
H18B	1.1040	0.1102	0.0114	0.147*
H18C	1.1184	0.0543	0.1010	0.147*
C19	0.7491 (2)	0.5051 (2)	0.1180 (3)	0.0720 (11)
H19A	0.7416	0.4974	0.0505	0.086*
H19B	0.7046	0.5370	0.1431	0.086*
H19C	0.7504	0.4528	0.1493	0.086*
C20	0.8274 (3)	0.6340 (2)	0.0864 (3)	0.0814 (13)
H20A	0.8767	0.6636	0.1007	0.098*
H20B	0.7810	0.6643	0.1091	0.098*
H20C	0.8230	0.6265	0.0184	0.098*
O3	0.93941 (16)	0.35332 (16)	0.89688 (17)	0.0823 (9)
H3A	0.8939	0.3773	0.8876	0.123*
H3B	0.9353	0.3018	0.8899	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0848 (18)	0.0794 (18)	0.0396 (14)	0.0071 (15)	−0.0011 (13)	0.0197 (13)
O2	0.098 (2)	0.0770 (18)	0.0413 (15)	0.0009 (15)	0.0157 (14)	−0.0102 (14)
N1	0.0477 (16)	0.0489 (16)	0.0336 (14)	0.0020 (13)	0.0067 (13)	0.0099 (14)
C1	0.048 (2)	0.076 (3)	0.0290 (16)	−0.0202 (18)	0.0011 (14)	0.0021 (17)
C2	0.0388 (18)	0.0462 (18)	0.0336 (16)	−0.0083 (15)	0.0007 (15)	0.0004 (15)
C3	0.0467 (19)	0.069 (2)	0.0251 (15)	−0.0136 (17)	−0.0057 (14)	−0.0009 (17)
C4	0.0340 (18)	0.046 (2)	0.0406 (18)	−0.0036 (16)	−0.0032 (15)	0.0039 (16)
C5	0.057 (2)	0.056 (2)	0.0424 (19)	0.0094 (18)	0.0024 (17)	0.0061 (17)
C6	0.085 (3)	0.063 (3)	0.049 (2)	0.031 (2)	0.007 (2)	0.0115 (19)
C7	0.082 (3)	0.077 (3)	0.058 (2)	0.028 (2)	0.000 (2)	0.019 (2)
C8	0.056 (2)	0.067 (2)	0.042 (2)	−0.0007 (19)	−0.0074 (18)	0.0095 (19)
C9	0.0387 (18)	0.048 (2)	0.039 (2)	−0.0070 (16)	−0.0027 (15)	0.0073 (16)
C10	0.0406 (18)	0.051 (2)	0.0310 (16)	−0.0099 (16)	−0.0054 (15)	0.0005 (15)
C11	0.0387 (19)	0.050 (2)	0.0349 (18)	−0.0101 (16)	0.0002 (15)	−0.0057 (17)
C12	0.060 (2)	0.057 (2)	0.041 (2)	−0.0097 (19)	−0.0004 (18)	−0.0092 (18)
C13	0.075 (3)	0.046 (2)	0.061 (2)	0.0021 (19)	0.006 (2)	−0.0106 (19)
C14	0.059 (2)	0.044 (2)	0.055 (2)	0.0036 (18)	0.0029 (18)	0.0016 (17)
C15	0.055 (2)	0.045 (2)	0.046 (2)	−0.0033 (18)	0.0008 (17)	0.0013 (16)
C16	0.0355 (18)	0.0426 (19)	0.0418 (18)	−0.0062 (16)	0.0012 (15)	−0.0032 (16)
C17	0.166 (5)	0.059 (3)	0.074 (3)	−0.008 (3)	−0.002 (3)	−0.002 (2)
C18	0.174 (5)	0.119 (4)	0.074 (3)	0.094 (4)	0.032 (3)	0.023 (3)
C19	0.057 (2)	0.088 (3)	0.071 (3)	0.011 (2)	−0.009 (2)	−0.003 (2)
C20	0.105 (3)	0.056 (2)	0.083 (3)	0.020 (2)	0.012 (3)	0.007 (2)
O3	0.0869 (19)	0.0827 (19)	0.077 (2)	−0.0024 (16)	−0.0127 (16)	−0.0029 (16)

Geometric parameters (Å, º)

O1—C8	1.235 (4)	C11—C16	1.361 (4)
O2—C12	1.237 (4)	C11—C12	1.448 (4)
N1—C16	1.370 (4)	C12—C13	1.513 (4)
N1—C4	1.382 (4)	C13—C14	1.534 (5)
N1—H1N	0.86	C13—H13A	0.97
C1—C1^i	1.366 (6)	C13—H13B	0.97
C1—C2	1.384 (4)	C14—C15	1.516 (4)
C1—H1	0.93	C14—C19	1.531 (5)
C2—C3	1.385 (4)	C14—C20	1.536 (5)
C2—C10	1.528 (4)	C15—C16	1.493 (4)
C3—C3^i	1.378 (6)	C15—H15A	0.97
C3—H3	0.93	C15—H15B	0.97
C4—C9	1.356 (4)	C17—H17A	0.96
C4—C5	1.473 (4)	C17—H17B	0.96
C5—C6	1.519 (5)	C17—H17C	0.96
C5—H5A	0.97	C18—H18A	0.96
C5—H5B	0.97	C18—H18B	0.96
C6—C7	1.523 (5)	C18—H18C	0.96
C6—C18	1.528 (5)	C19—H19A	0.96
C6—C17	1.531 (6)	C19—H19B	0.96
C7—C8	1.507 (5)	C19—H19C	0.96
C7—H7A	0.97	C20—H20A	0.96
C7—H7B	0.97	C20—H20B	0.96
C8—C9	1.449 (4)	C20—H20C	0.96
C9—C10	1.513 (4)	O3—H3A	0.85
C10—C11	1.505 (4)	O3—H3B	0.85
C10—H10	0.98
C16—N1—C4	122.7 (3)	O2—C12—C13	119.8 (3)
C16—N1—H1N	118.6	C11—C12—C13	119.0 (3)
C4—N1—H1N	118.6	C12—C13—C14	112.2 (3)
C1^i—C1—C2	121.04 (16)	C12—C13—H13A	109.2
C1^i—C1—H1	119.5	C14—C13—H13A	109.2
C2—C1—H1	119.5	C12—C13—H13B	109.2
C1—C2—C3	118.2 (3)	C14—C13—H13B	109.2
C1—C2—C10	119.2 (2)	H13A—C13—H13B	107.9
C3—C2—C10	122.6 (2)	C15—C14—C19	110.9 (3)
C3^i—C3—C2	120.73 (16)	C15—C14—C13	107.9 (3)
C3^i—C3—H3	119.6	C19—C14—C13	110.1 (3)
C2—C3—H3	119.6	C15—C14—C20	109.2 (3)
C9—C4—N1	119.3 (3)	C19—C14—C20	109.4 (3)
C9—C4—C5	124.8 (3)	C13—C14—C20	109.4 (3)
N1—C4—C5	115.9 (3)	C16—C15—C14	113.5 (3)
C4—C5—C6	113.4 (3)	C16—C15—H15A	108.9
C4—C5—H5A	108.9	C14—C15—H15A	108.9
C6—C5—H5A	108.9	C16—C15—H15B	108.9
C4—C5—H5B	108.9	C14—C15—H15B	108.9
C6—C5—H5B	108.9	H15A—C15—H15B	107.7
H5A—C5—H5B	107.7	C11—C16—N1	120.0 (3)
C5—C6—C7	108.5 (3)	C11—C16—C15	124.0 (3)
C5—C6—C18	108.5 (3)	N1—C16—C15	116.0 (3)
C7—C6—C18	111.7 (3)	C6—C17—H17A	109.5
C5—C6—C17	110.3 (3)	C6—C17—H17B	109.5
C7—C6—C17	109.5 (3)	H17A—C17—H17B	109.5
C18—C6—C17	108.3 (4)	C6—C17—H17C	109.5
C8—C7—C6	112.7 (3)	H17A—C17—H17C	109.5
C8—C7—H7A	109.0	H17B—C17—H17C	109.5
C6—C7—H7A	109.0	C6—C18—H18A	109.5
C8—C7—H7B	109.0	C6—C18—H18B	109.5
C6—C7—H7B	109.0	H18A—C18—H18B	109.5
H7A—C7—H7B	107.8	C6—C18—H18C	109.5
O1—C8—C9	122.0 (3)	H18A—C18—H18C	109.5
O1—C8—C7	119.7 (3)	H18B—C18—H18C	109.5
C9—C8—C7	118.3 (3)	C14—C19—H19A	109.5
C4—C9—C8	118.7 (3)	C14—C19—H19B	109.5
C4—C9—C10	122.0 (3)	H19A—C19—H19B	109.5
C8—C9—C10	118.9 (3)	C14—C19—H19C	109.5
C11—C10—C9	110.0 (2)	H19A—C19—H19C	109.5
C11—C10—C2	110.2 (2)	H19B—C19—H19C	109.5
C9—C10—C2	110.1 (2)	C14—C20—H20A	109.5
C11—C10—H10	108.8	C14—C20—H20B	109.5
C9—C10—H10	108.8	H20A—C20—H20B	109.5
C2—C10—H10	108.8	C14—C20—H20C	109.5
C16—C11—C12	118.6 (3)	H20A—C20—H20C	109.5
C16—C11—C10	121.6 (3)	H20B—C20—H20C	109.5
C12—C11—C10	119.2 (3)	H3A—O3—H3B	111.6
O2—C12—C11	121.2 (3)
C1^i—C1—C2—C3	0.3 (6)	C1—C2—C10—C11	61.5 (4)
C1^i—C1—C2—C10	−180.0 (4)	C3—C2—C10—C11	−118.8 (3)
C1—C2—C3—C3^i	−0.7 (6)	C1—C2—C10—C9	−60.0 (4)
C10—C2—C3—C3^i	179.6 (3)	C3—C2—C10—C9	119.7 (3)
C16—N1—C4—C9	7.4 (4)	C9—C10—C11—C16	21.7 (4)
C16—N1—C4—C5	−171.9 (3)	C2—C10—C11—C16	−99.9 (3)
C9—C4—C5—C6	21.4 (5)	C9—C10—C11—C12	−167.2 (3)
N1—C4—C5—C6	−159.3 (3)	C2—C10—C11—C12	71.3 (3)
C4—C5—C6—C7	−47.2 (4)	C16—C11—C12—O2	172.4 (3)
C4—C5—C6—C18	−168.8 (3)	C10—C11—C12—O2	1.1 (5)
C4—C5—C6—C17	72.7 (4)	C16—C11—C12—C13	−5.9 (4)
C5—C6—C7—C8	54.5 (4)	C10—C11—C12—C13	−177.3 (3)
C18—C6—C7—C8	174.0 (3)	O2—C12—C13—C14	−143.4 (3)
C17—C6—C7—C8	−66.0 (4)	C11—C12—C13—C14	35.0 (4)
C6—C7—C8—O1	144.8 (4)	C12—C13—C14—C15	−55.2 (4)
C6—C7—C8—C9	−35.6 (5)	C12—C13—C14—C19	65.9 (4)
N1—C4—C9—C8	−178.9 (3)	C12—C13—C14—C20	−173.9 (3)
C5—C4—C9—C8	0.3 (5)	C19—C14—C15—C16	−71.4 (4)
N1—C4—C9—C10	8.7 (4)	C13—C14—C15—C16	49.1 (4)
C5—C4—C9—C10	−172.0 (3)	C20—C14—C15—C16	168.0 (3)
O1—C8—C9—C4	−173.4 (3)	C12—C11—C16—N1	−179.9 (3)
C7—C8—C9—C4	7.0 (5)	C10—C11—C16—N1	−8.8 (4)
O1—C8—C9—C10	−0.8 (5)	C12—C11—C16—C15	−0.5 (4)
C7—C8—C9—C10	179.6 (3)	C10—C11—C16—C15	170.7 (3)
C4—C9—C10—C11	−21.8 (4)	C4—N1—C16—C11	−7.4 (4)
C8—C9—C10—C11	165.9 (3)	C4—N1—C16—C15	173.1 (3)
C4—C9—C10—C2	99.8 (3)	C14—C15—C16—C11	−22.9 (4)
C8—C9—C10—C2	−72.5 (3)	C14—C15—C16—N1	156.5 (3)

Symmetry code: (i) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^ii	0.86	2.16	2.959 (3)	155
O3—H3A···O1^iii	0.85	2.19	2.991 (4)	157
O3—H3B···O2^iv	0.85	2.20	3.008 (4)	159

Symmetry codes: (ii) x, y, z−1; (iii) −y+1, x−1/2, z+1/2; (iv) y+1/2, −x+1, z+1/2.