9-(2,6-Dihydroxy­phen­yl)-3,3,6,6-tetra­meth­yl-N-(4-methyl­phen­yl)-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine

The title compound, C₃₀H₃₃NO₄, was synthesized by the reaction of 2,6-dihydroxy­benzaldehyde with p-toluidine and 5,5-dimethyl­cyclo­hexa­ne-1,3-dione in glycol under microwave irradition. X-ray analysis reveals that the dihydro­pyridine ring is in a distorted boat conformation and that the cyclo­hexenone rings adopt enevelope conformations. In the crystal structure, mol­ecules are linked by O—H...O hydrogen bonds around a centre of symmetry to form a dimer.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.073
• wR factor = 0.219
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C26     ..       9.43 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C26    -   C27     ..       8.32 su

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   7 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: SHELXTL.

9-(2,6-Dihydroxyphenyl)-3,3,6,6-tetramethyl-N-(4-methylphenyl)- 1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydroacridine

Crystal data

C30H33NO4	F(000) = 1008
Mr = 471.57	Dx = 1.213 Mg m^−3
Monoclinic, P21/c	Melting point = 531–532 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.995 (4) Å	Cell parameters from 1094 reflections
b = 11.002 (4) Å	θ = 2.4–19.3°
c = 19.965 (7) Å	µ = 0.08 mm^−1
β = 101.419 (6)°	T = 298 K
V = 2582.5 (15) Å^3	Block, light-yellow
Z = 4	0.38 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4544 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.118
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.970, Tmax = 0.988	k = −13→9
13000 measured reflections	l = −23→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.219	w = 1/[σ^2(Fo^2) + (0.072P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4544 reflections	Δρmax = 0.31 e Å^−3
324 parameters	Δρmin = −0.27 e Å^−3
20 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (10)

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
N1	0.7046 (4)	0.5555 (4)	0.1319 (2)	0.0475 (12)
O1	0.5722 (4)	0.1677 (3)	0.1774 (2)	0.0723 (13)
O2	0.5834 (4)	0.3107 (4)	−0.06103 (18)	0.0705 (13)
O3	0.9108 (3)	0.3687 (3)	0.12673 (17)	0.0440 (10)
H3	0.8638	0.4239	0.1217	0.066*
O4	0.5942 (4)	0.0468 (4)	0.03250 (18)	0.0760 (14)
H4	0.5576	0.0826	−0.0008	0.114*
C1	0.6748 (4)	0.4674 (5)	0.1751 (3)	0.0450 (14)
C2	0.6754 (5)	0.5075 (5)	0.2478 (3)	0.0637 (18)
H2A	0.6063	0.5529	0.2485	0.076*
H2B	0.7392	0.5619	0.2624	0.076*
C3	0.6836 (6)	0.4030 (5)	0.2982 (3)	0.0601 (17)
C4	0.5961 (5)	0.3096 (5)	0.2677 (3)	0.0607 (17)
H4A	0.6048	0.2389	0.2973	0.073*
H4B	0.5210	0.3430	0.2669	0.073*
C5	0.6025 (5)	0.2696 (5)	0.1974 (3)	0.0498 (15)
C6	0.6452 (4)	0.3554 (5)	0.1528 (2)	0.0428 (14)
C7	0.6464 (5)	0.3135 (5)	0.0811 (2)	0.0458 (15)
H7	0.5734	0.2738	0.0635	0.055*
C8	0.6544 (4)	0.4223 (5)	0.0372 (2)	0.0421 (14)
C9	0.6241 (5)	0.4071 (6)	−0.0364 (3)	0.0491 (15)
C10	0.6385 (5)	0.5104 (5)	−0.0826 (3)	0.0589 (17)
H10A	0.5665	0.5526	−0.0955	0.071*
H10B	0.6578	0.4778	−0.1240	0.071*
C11	0.7293 (5)	0.6014 (5)	−0.0515 (3)	0.0579 (16)
C12	0.7052 (5)	0.6397 (4)	0.0179 (2)	0.0496 (15)
H12A	0.7685	0.6879	0.0417	0.059*
H12B	0.6379	0.6907	0.0107	0.059*
C13	0.6870 (4)	0.5331 (5)	0.0627 (3)	0.0461 (14)
C14	0.6576 (6)	0.4514 (5)	0.3652 (3)	0.089 (2)
H14A	0.7190	0.5024	0.3872	0.134*
H14B	0.6491	0.3845	0.3947	0.134*
H14C	0.5885	0.4978	0.3559	0.134*
C15	0.8022 (6)	0.3457 (6)	0.3111 (3)	0.089 (2)
H15A	0.8585	0.4079	0.3239	0.134*
H15B	0.8141	0.3062	0.2702	0.134*
H15C	0.8083	0.2871	0.3473	0.134*
C16	0.7227 (6)	0.7142 (5)	−0.0971 (3)	0.081 (2)
H16A	0.7801	0.7713	−0.0769	0.121*
H16B	0.6490	0.7509	−0.1015	0.121*
H16C	0.7350	0.6909	−0.1414	0.121*
C17	0.8463 (5)	0.5426 (6)	−0.0428 (3)	0.080 (2)
H17A	0.9036	0.6006	−0.0237	0.120*
H17B	0.8590	0.5162	−0.0866	0.120*
H17C	0.8501	0.4739	−0.0128	0.120*
C18	0.7406 (5)	0.6744 (5)	0.1583 (3)	0.0514 (15)
C19	0.8538 (6)	0.6939 (6)	0.1858 (3)	0.0739 (19)
H19	0.9068	0.6324	0.1853	0.089*
C20	0.8882 (6)	0.8073 (7)	0.2144 (3)	0.073 (2)
H20	0.9646	0.8205	0.2332	0.087*
C21	0.8120 (6)	0.8985 (6)	0.2153 (3)	0.0615 (17)
C22	0.7014 (6)	0.8778 (5)	0.1870 (3)	0.0642 (18)
H22	0.6490	0.9401	0.1867	0.077*
C23	0.6638 (5)	0.7668 (5)	0.1585 (3)	0.0521 (16)
H23	0.5872	0.7550	0.1396	0.063*
C24	0.8521 (6)	1.0211 (5)	0.2456 (3)	0.086 (2)
H24A	0.9098	1.0094	0.2859	0.129*
H24B	0.7890	1.0642	0.2574	0.129*
H24C	0.8828	1.0674	0.2128	0.129*
C25	0.7410 (6)	0.2208 (5)	0.0776 (3)	0.0527 (16)
C26	0.8553 (6)	0.2551 (6)	0.0984 (3)	0.074 (2)
C27	0.9376 (8)	0.1672 (9)	0.0926 (4)	0.111 (3)
H27	1.0145	0.1862	0.1050	0.133*
C28	0.9051 (9)	0.0541 (10)	0.0687 (4)	0.116 (3)
H28	0.9617	−0.0026	0.0663	0.139*
C29	0.7962 (9)	0.0194 (7)	0.0485 (4)	0.101 (3)
H29	0.7786	−0.0586	0.0318	0.122*
C30	0.7075 (6)	0.1046 (6)	0.0532 (3)	0.073 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.076 (4)	0.029 (3)	0.038 (3)	−0.004 (2)	0.013 (2)	−0.006 (2)
O1	0.094 (4)	0.050 (3)	0.077 (3)	−0.025 (2)	0.029 (2)	−0.009 (2)
O2	0.094 (3)	0.059 (3)	0.051 (2)	−0.005 (2)	−0.003 (2)	−0.013 (2)
O3	0.025 (2)	0.051 (2)	0.054 (2)	0.0052 (18)	0.0023 (18)	0.003 (2)
O4	0.129 (4)	0.053 (3)	0.043 (2)	−0.039 (3)	0.010 (2)	−0.013 (2)
C1	0.052 (4)	0.043 (4)	0.042 (3)	−0.002 (3)	0.014 (3)	0.001 (3)
C2	0.095 (5)	0.053 (4)	0.047 (4)	−0.004 (3)	0.021 (4)	0.000 (3)
C3	0.099 (6)	0.048 (4)	0.035 (3)	0.001 (4)	0.018 (3)	−0.002 (3)
C4	0.088 (5)	0.050 (4)	0.049 (4)	−0.005 (4)	0.025 (3)	0.004 (3)
C5	0.052 (4)	0.044 (4)	0.054 (4)	−0.009 (3)	0.014 (3)	−0.003 (3)
C6	0.045 (4)	0.041 (4)	0.044 (3)	−0.002 (3)	0.013 (3)	0.002 (3)
C7	0.052 (4)	0.048 (4)	0.036 (3)	−0.010 (3)	0.005 (3)	−0.006 (3)
C8	0.047 (4)	0.044 (4)	0.037 (3)	−0.002 (3)	0.012 (3)	−0.007 (3)
C9	0.047 (4)	0.056 (4)	0.043 (4)	0.010 (3)	0.004 (3)	−0.003 (3)
C10	0.070 (5)	0.063 (4)	0.046 (4)	0.010 (4)	0.014 (3)	−0.001 (3)
C11	0.070 (5)	0.056 (4)	0.049 (4)	0.007 (4)	0.016 (3)	0.003 (3)
C12	0.064 (4)	0.042 (4)	0.043 (3)	−0.004 (3)	0.011 (3)	−0.001 (3)
C13	0.050 (4)	0.047 (4)	0.044 (4)	0.000 (3)	0.013 (3)	0.000 (3)
C14	0.159 (7)	0.064 (4)	0.047 (4)	0.000 (5)	0.027 (4)	0.000 (3)
C15	0.104 (6)	0.086 (5)	0.071 (5)	0.011 (5)	−0.002 (4)	−0.001 (4)
C16	0.120 (6)	0.064 (4)	0.061 (4)	0.002 (4)	0.026 (4)	0.009 (4)
C17	0.068 (5)	0.088 (5)	0.087 (5)	0.016 (4)	0.025 (4)	0.014 (4)
C18	0.058 (4)	0.044 (4)	0.051 (4)	−0.004 (3)	0.010 (3)	−0.004 (3)
C19	0.063 (5)	0.077 (5)	0.077 (5)	0.004 (4)	0.003 (4)	−0.002 (4)
C20	0.061 (5)	0.076 (5)	0.072 (5)	−0.023 (4)	−0.006 (4)	−0.004 (4)
C21	0.070 (5)	0.055 (4)	0.058 (4)	−0.018 (4)	0.008 (4)	0.004 (3)
C22	0.077 (5)	0.046 (4)	0.072 (4)	−0.005 (4)	0.021 (4)	−0.004 (3)
C23	0.053 (4)	0.047 (4)	0.056 (4)	−0.004 (3)	0.010 (3)	−0.001 (3)
C24	0.108 (6)	0.064 (5)	0.081 (5)	−0.033 (4)	0.003 (4)	−0.016 (4)
C25	0.069 (5)	0.046 (4)	0.045 (4)	0.002 (3)	0.015 (3)	0.000 (3)
C26	0.070 (6)	0.089 (6)	0.067 (5)	0.022 (5)	0.022 (4)	0.015 (4)
C27	0.102 (6)	0.142 (7)	0.094 (5)	0.000 (6)	0.032 (5)	0.035 (5)
C28	0.141 (7)	0.132 (7)	0.084 (6)	0.051 (6)	0.048 (5)	0.040 (5)
C29	0.168 (7)	0.076 (5)	0.070 (5)	0.029 (6)	0.047 (5)	0.009 (4)
C30	0.117 (6)	0.056 (5)	0.052 (4)	0.002 (5)	0.036 (4)	−0.003 (4)

Geometric parameters (Å, º)

N1—C13	1.377 (6)	C12—H12B	0.97
N1—C1	1.391 (6)	C14—H14A	0.96
N1—C18	1.445 (6)	C14—H14B	0.96
O1—C5	1.220 (5)	C14—H14C	0.96
O2—C9	1.229 (6)	C15—H15A	0.96
O3—C26	1.475 (6)	C15—H15B	0.96
O3—H3	0.82	C15—H15C	0.96
O4—C30	1.484 (6)	C16—H16A	0.96
O4—H4	0.82	C16—H16B	0.96
C1—C6	1.335 (6)	C16—H16C	0.96
C1—C2	1.515 (7)	C17—H17A	0.96
C2—C3	1.519 (7)	C17—H17B	0.96
C2—H2A	0.97	C17—H17C	0.96
C2—H2B	0.97	C18—C23	1.373 (7)
C3—C4	1.509 (7)	C18—C19	1.376 (7)
C3—C14	1.529 (7)	C19—C20	1.401 (8)
C3—C15	1.530 (8)	C19—H19	0.93
C4—C5	1.486 (7)	C20—C21	1.360 (8)
C4—H4A	0.97	C20—H20	0.93
C4—H4B	0.97	C21—C22	1.355 (8)
C5—C6	1.459 (7)	C21—C24	1.518 (7)
C6—C7	1.505 (7)	C22—C23	1.384 (7)
C7—C8	1.497 (6)	C22—H22	0.93
C7—C25	1.537 (7)	C23—H23	0.93
C7—H7	0.98	C24—H24A	0.96
C8—C13	1.350 (6)	C24—H24B	0.96
C8—C9	1.452 (7)	C24—H24C	0.96
C9—C10	1.496 (7)	C25—C30	1.399 (8)
C10—C11	1.518 (7)	C25—C26	1.404 (8)
C10—H10A	0.97	C26—C27	1.403 (10)
C10—H10B	0.97	C27—C28	1.362 (10)
C11—C17	1.525 (7)	C27—H27	0.93
C11—C12	1.530 (7)	C28—C29	1.344 (10)
C11—C16	1.531 (7)	C28—H28	0.93
C12—C13	1.516 (6)	C29—C30	1.434 (9)
C12—H12A	0.97	C29—H29	0.93
C13—N1—C1	119.4 (4)	C3—C14—H14B	109.5
C13—N1—C18	120.2 (4)	H14A—C14—H14B	109.5
C1—N1—C18	120.0 (4)	C3—C14—H14C	109.5
C26—O3—H3	109.5	H14A—C14—H14C	109.5
C30—O4—H4	109.5	H14B—C14—H14C	109.5
C6—C1—N1	121.3 (5)	C3—C15—H15A	109.5
C6—C1—C2	122.7 (5)	C3—C15—H15B	109.5
N1—C1—C2	116.0 (5)	H15A—C15—H15B	109.5
C1—C2—C3	113.7 (4)	C3—C15—H15C	109.5
C1—C2—H2A	108.8	H15A—C15—H15C	109.5
C3—C2—H2A	108.8	H15B—C15—H15C	109.5
C1—C2—H2B	108.8	C11—C16—H16A	109.5
C3—C2—H2B	108.8	C11—C16—H16B	109.5
H2A—C2—H2B	107.7	H16A—C16—H16B	109.5
C4—C3—C2	107.4 (5)	C11—C16—H16C	109.5
C4—C3—C14	110.2 (5)	H16A—C16—H16C	109.5
C2—C3—C14	108.6 (5)	H16B—C16—H16C	109.5
C4—C3—C15	109.6 (5)	C11—C17—H17A	109.5
C2—C3—C15	111.1 (5)	C11—C17—H17B	109.5
C14—C3—C15	109.9 (5)	H17A—C17—H17B	109.5
C5—C4—C3	115.0 (5)	C11—C17—H17C	109.5
C5—C4—H4A	108.5	H17A—C17—H17C	109.5
C3—C4—H4A	108.5	H17B—C17—H17C	109.5
C5—C4—H4B	108.5	C23—C18—C19	119.6 (6)
C3—C4—H4B	108.5	C23—C18—N1	121.2 (5)
H4A—C4—H4B	107.5	C19—C18—N1	119.1 (6)
O1—C5—C6	120.7 (5)	C18—C19—C20	119.3 (6)
O1—C5—C4	120.9 (5)	C18—C19—H19	120.3
C6—C5—C4	118.3 (5)	C20—C19—H19	120.3
C1—C6—C5	119.7 (5)	C21—C20—C19	121.2 (6)
C1—C6—C7	123.3 (5)	C21—C20—H20	119.4
C5—C6—C7	117.0 (5)	C19—C20—H20	119.4
C8—C7—C6	109.0 (4)	C22—C21—C20	118.4 (6)
C8—C7—C25	111.7 (4)	C22—C21—C24	121.5 (7)
C6—C7—C25	113.1 (4)	C20—C21—C24	120.0 (6)
C8—C7—H7	107.6	C21—C22—C23	122.2 (6)
C6—C7—H7	107.6	C21—C22—H22	118.9
C25—C7—H7	107.6	C23—C22—H22	118.9
C13—C8—C9	118.8 (5)	C18—C23—C22	119.3 (6)
C13—C8—C7	123.3 (5)	C18—C23—H23	120.3
C9—C8—C7	118.0 (5)	C22—C23—H23	120.3
O2—C9—C8	120.3 (5)	C21—C24—H24A	109.5
O2—C9—C10	119.6 (5)	C21—C24—H24B	109.5
C8—C9—C10	120.1 (5)	H24A—C24—H24B	109.5
C9—C10—C11	114.2 (5)	C21—C24—H24C	109.5
C9—C10—H10A	108.7	H24A—C24—H24C	109.5
C11—C10—H10A	108.7	H24B—C24—H24C	109.5
C9—C10—H10B	108.7	C30—C25—C26	123.0 (6)
C11—C10—H10B	108.7	C30—C25—C7	117.4 (6)
H10A—C10—H10B	107.6	C26—C25—C7	119.6 (5)
C10—C11—C17	109.6 (5)	C27—C26—C25	116.9 (7)
C10—C11—C12	107.7 (5)	C27—C26—O3	110.2 (7)
C17—C11—C12	110.4 (5)	C25—C26—O3	132.9 (6)
C10—C11—C16	110.0 (5)	C28—C27—C26	120.1 (9)
C17—C11—C16	110.4 (5)	C28—C27—H27	119.9
C12—C11—C16	108.6 (5)	C26—C27—H27	119.9
C13—C12—C11	113.4 (4)	C29—C28—C27	123.9 (10)
C13—C12—H12A	108.9	C29—C28—H28	118.0
C11—C12—H12A	108.9	C27—C28—H28	118.0
C13—C12—H12B	108.9	C28—C29—C30	119.0 (8)
C11—C12—H12B	108.9	C28—C29—H29	120.5
H12A—C12—H12B	107.7	C30—C29—H29	120.5
C8—C13—N1	121.0 (5)	C25—C30—C29	117.1 (7)
C8—C13—C12	122.8 (5)	C25—C30—O4	132.3 (6)
N1—C13—C12	116.2 (5)	C29—C30—O4	110.6 (6)
C3—C14—H14A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	2.44	3.233 (6)	164
O4—H4···O4^i	0.82	2.30	2.587 (6)	101

Symmetry code: (i) −x+1, −y, −z.