3,3,6,6-Tetra­methyl-9-(2-oxo-1,2-dihydro­quinolin-3-yl)-1,2,3,4,5,6,7,8-octa­hydro-9H-xanthene-1,8-dione

In the title compound, C₂₆H₂₇NO₄, the central ring of the xanthene moiety is planar and the two outer rings are in half-boat conformations. The mol­ecular packing in the crystal structure is stabilized by N—H...O and C—H...O hydrogen bonds in addition to van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

3,3,6,6-Tetramethyl-9-(2-oxo-1,2-dihydroquinolin-3-yl)- 1,2,3,4,5,6,7,8-octahydro-9H-xanthene-1,8-dione

Crystal data

C26H27NO4	F(000) = 1776
Mr = 417.49	Dx = 1.210 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 6390 reflections
a = 22.2713 (12) Å	θ = 2.3–27.5°
b = 11.9162 (6) Å	µ = 0.08 mm^−1
c = 17.2698 (9) Å	T = 293 K
V = 4583.2 (4) Å^3	Block, colourless
Z = 8	0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3862 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −28→26
26484 measured reflections	k = −15→15
5325 independent reflections	l = −21→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0719P)^2 + 0.8427P] where P = (Fo^2 + 2Fc^2)/3
5325 reflections	(Δ/σ)max = 0.001
284 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.17 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
C1	0.53660 (7)	0.37706 (13)	0.21155 (9)	0.0502 (4)
C2	0.54765 (8)	0.44718 (15)	0.28275 (9)	0.0593 (4)
H2A	0.5471	0.3984	0.3277	0.071*
H2B	0.5149	0.5002	0.2883	0.071*
C3	0.60660 (8)	0.51179 (15)	0.28202 (9)	0.0581 (4)
C4	0.60939 (9)	0.57954 (13)	0.20681 (9)	0.0547 (4)
H4A	0.5804	0.6402	0.2092	0.066*
H4B	0.6490	0.6124	0.2015	0.066*
C5	0.59646 (6)	0.50832 (11)	0.13802 (8)	0.0409 (3)
C6	0.60615 (6)	0.50235 (11)	0.00233 (8)	0.0405 (3)
C7	0.63064 (8)	0.56585 (14)	−0.06504 (9)	0.0558 (4)
H7A	0.6692	0.5979	−0.0511	0.067*
H7B	0.6036	0.6271	−0.0776	0.067*
C8	0.63842 (8)	0.49089 (15)	−0.13627 (9)	0.0585 (4)
C9	0.57980 (8)	0.42765 (16)	−0.14896 (10)	0.0632 (5)
H9A	0.5493	0.4807	−0.1654	0.076*
H9B	0.5855	0.3742	−0.1907	0.076*
C10	0.55693 (7)	0.36566 (13)	−0.07901 (9)	0.0504 (4)
C11	0.57397 (6)	0.40840 (10)	−0.00256 (8)	0.0383 (3)
C12	0.55694 (6)	0.34164 (10)	0.06795 (8)	0.0378 (3)
H12	0.5144	0.3213	0.0636	0.045*
C13	0.56447 (6)	0.41349 (10)	0.13870 (8)	0.0392 (3)
C14	0.65931 (10)	0.42979 (19)	0.28597 (13)	0.0841 (6)
H14A	0.6580	0.3897	0.3342	0.126*
H14B	0.6964	0.4706	0.2824	0.126*
H14C	0.6567	0.3775	0.2438	0.126*
C15	0.60929 (12)	0.5928 (2)	0.35107 (11)	0.0865 (7)
H15A	0.5767	0.6454	0.3477	0.130*
H15B	0.6467	0.6327	0.3502	0.130*
H15C	0.6061	0.5511	0.3984	0.130*
C16	0.68962 (9)	0.40783 (19)	−0.12314 (13)	0.0800 (6)
H16A	0.6802	0.3605	−0.0798	0.120*
H16B	0.7260	0.4482	−0.1127	0.120*
H16C	0.6948	0.3625	−0.1686	0.120*
C17	0.65207 (13)	0.5648 (2)	−0.20702 (12)	0.0919 (7)
H17A	0.6565	0.5183	−0.2520	0.138*
H17B	0.6886	0.6057	−0.1983	0.138*
H17C	0.6197	0.6167	−0.2149	0.138*
C18	0.59344 (6)	0.23413 (10)	0.07274 (8)	0.0366 (3)
C19	0.56765 (6)	0.13177 (11)	0.07021 (8)	0.0389 (3)
H19	0.5260	0.1272	0.0676	0.047*
C20	0.60159 (6)	0.03023 (10)	0.07141 (8)	0.0387 (3)
C21	0.57547 (7)	−0.07704 (12)	0.06921 (9)	0.0463 (4)
H21	0.5339	−0.0841	0.0677	0.056*
C22	0.61048 (8)	−0.17098 (12)	0.06934 (10)	0.0567 (4)
H22	0.5928	−0.2416	0.0676	0.068*
C23	0.67222 (9)	−0.16101 (13)	0.07199 (11)	0.0624 (5)
H23	0.6957	−0.2256	0.0720	0.075*
C24	0.69986 (8)	−0.05758 (12)	0.07468 (10)	0.0544 (4)
H24	0.7415	−0.0520	0.0764	0.065*
C25	0.66409 (7)	0.03868 (10)	0.07473 (8)	0.0397 (3)
C26	0.65860 (6)	0.24267 (10)	0.07820 (8)	0.0396 (3)
N1	0.68953 (5)	0.14412 (9)	0.07830 (7)	0.0436 (3)
H1	0.7280	0.1479	0.0808	0.052*
O1	0.62153 (5)	0.55121 (8)	0.07150 (5)	0.0458 (3)
O2	0.50464 (6)	0.29427 (11)	0.21297 (7)	0.0748 (4)
O3	0.52450 (7)	0.28391 (12)	−0.08490 (8)	0.0778 (4)
O4	0.68593 (4)	0.33347 (8)	0.08224 (7)	0.0502 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0466 (9)	0.0513 (8)	0.0527 (9)	0.0033 (7)	0.0068 (7)	0.0093 (7)
C2	0.0632 (11)	0.0696 (10)	0.0450 (8)	0.0082 (9)	0.0059 (7)	0.0067 (7)
C3	0.0646 (11)	0.0622 (10)	0.0475 (9)	0.0064 (8)	−0.0073 (8)	−0.0015 (7)
C4	0.0671 (11)	0.0455 (8)	0.0515 (9)	−0.0026 (7)	−0.0004 (8)	−0.0060 (7)
C5	0.0432 (8)	0.0338 (6)	0.0457 (8)	0.0058 (6)	0.0035 (6)	0.0010 (5)
C6	0.0425 (8)	0.0339 (6)	0.0451 (7)	0.0057 (6)	0.0050 (6)	0.0004 (5)
C7	0.0646 (11)	0.0481 (8)	0.0546 (9)	−0.0049 (7)	0.0086 (8)	0.0076 (7)
C8	0.0626 (11)	0.0651 (10)	0.0479 (9)	0.0021 (8)	0.0109 (7)	0.0042 (7)
C9	0.0654 (12)	0.0753 (11)	0.0487 (9)	0.0045 (9)	−0.0038 (8)	−0.0009 (8)
C10	0.0429 (9)	0.0542 (9)	0.0542 (9)	0.0022 (7)	−0.0037 (7)	−0.0047 (7)
C11	0.0316 (7)	0.0357 (6)	0.0475 (7)	0.0063 (5)	0.0013 (6)	−0.0004 (5)
C12	0.0271 (7)	0.0337 (6)	0.0526 (8)	0.0013 (5)	0.0016 (6)	0.0001 (5)
C13	0.0350 (7)	0.0352 (6)	0.0472 (7)	0.0071 (5)	0.0028 (6)	0.0026 (5)
C14	0.0697 (14)	0.0961 (15)	0.0864 (15)	0.0172 (12)	−0.0239 (11)	0.0027 (12)
C15	0.1105 (18)	0.0962 (15)	0.0529 (11)	0.0015 (14)	−0.0081 (11)	−0.0123 (10)
C16	0.0614 (12)	0.0972 (15)	0.0815 (14)	0.0133 (11)	0.0225 (10)	−0.0011 (11)
C17	0.1145 (19)	0.1049 (16)	0.0564 (12)	−0.0113 (15)	0.0215 (11)	0.0152 (11)
C18	0.0301 (7)	0.0307 (6)	0.0489 (7)	0.0003 (5)	0.0014 (6)	0.0000 (5)
C19	0.0294 (7)	0.0362 (7)	0.0512 (8)	−0.0034 (5)	0.0015 (6)	−0.0006 (6)
C20	0.0393 (8)	0.0312 (6)	0.0456 (7)	−0.0043 (5)	0.0044 (6)	−0.0001 (5)
C21	0.0445 (9)	0.0364 (7)	0.0581 (9)	−0.0090 (6)	0.0052 (7)	−0.0017 (6)
C22	0.0622 (11)	0.0289 (6)	0.0788 (11)	−0.0062 (7)	0.0061 (9)	−0.0009 (7)
C23	0.0619 (11)	0.0306 (7)	0.0947 (14)	0.0089 (7)	0.0069 (9)	0.0003 (7)
C24	0.0435 (9)	0.0369 (7)	0.0828 (12)	0.0051 (6)	0.0056 (8)	0.0010 (7)
C25	0.0376 (8)	0.0304 (6)	0.0510 (8)	−0.0014 (5)	0.0038 (6)	0.0009 (5)
C26	0.0328 (7)	0.0290 (6)	0.0569 (8)	−0.0013 (5)	0.0015 (6)	0.0007 (5)
N1	0.0279 (6)	0.0313 (6)	0.0717 (8)	0.0003 (4)	0.0010 (5)	0.0003 (5)
O1	0.0569 (7)	0.0324 (5)	0.0481 (6)	−0.0065 (4)	0.0062 (5)	−0.0016 (4)
O2	0.0806 (9)	0.0737 (8)	0.0702 (8)	−0.0252 (7)	0.0195 (7)	0.0095 (6)
O3	0.0815 (10)	0.0823 (9)	0.0695 (8)	−0.0332 (8)	−0.0104 (7)	−0.0120 (7)
O4	0.0309 (5)	0.0301 (5)	0.0896 (8)	−0.0026 (4)	−0.0009 (5)	−0.0010 (5)

Geometric parameters (Å, º)

C1—O2	1.2168 (19)	C12—H12	0.9800
C1—C13	1.468 (2)	C14—H14A	0.9600
C1—C2	1.507 (2)	C14—H14B	0.9600
C2—C3	1.522 (3)	C14—H14C	0.9600
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C3—C14	1.529 (3)	C15—H15C	0.9600
C3—C4	1.530 (2)	C16—H16A	0.9600
C3—C15	1.536 (2)	C16—H16B	0.9600
C4—C5	1.488 (2)	C16—H16C	0.9600
C4—H4A	0.9700	C17—H17A	0.9600
C4—H4B	0.9700	C17—H17B	0.9600
C5—C13	1.3359 (19)	C17—H17C	0.9600
C5—O1	1.3758 (16)	C18—C19	1.3489 (17)
C6—C11	1.3319 (19)	C18—C26	1.458 (2)
C6—O1	1.3723 (17)	C19—C20	1.4268 (18)
C6—C7	1.491 (2)	C19—H19	0.9300
C7—C8	1.530 (2)	C20—C25	1.397 (2)
C7—H7A	0.9700	C20—C21	1.4049 (18)
C7—H7B	0.9700	C21—C22	1.364 (2)
C8—C9	1.523 (2)	C21—H21	0.9300
C8—C16	1.527 (3)	C22—C23	1.381 (3)
C8—C17	1.537 (2)	C22—H22	0.9300
C9—C10	1.505 (2)	C23—C24	1.378 (2)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—C25	1.3966 (19)
C10—O3	1.2170 (19)	C24—H24	0.9300
C10—C11	1.465 (2)	C25—N1	1.3797 (16)
C11—C12	1.5032 (18)	C26—O4	1.2435 (15)
C12—C13	1.5014 (18)	C26—N1	1.3614 (16)
C12—C18	1.5195 (17)	N1—H1	0.8600
O2—C1—C13	120.28 (14)	C5—C13—C12	122.33 (12)
O2—C1—C2	121.91 (14)	C1—C13—C12	118.78 (12)
C13—C1—C2	117.79 (14)	C3—C14—H14A	109.5
C1—C2—C3	114.49 (13)	C3—C14—H14B	109.5
C1—C2—H2A	108.6	H14A—C14—H14B	109.5
C3—C2—H2A	108.6	C3—C14—H14C	109.5
C1—C2—H2B	108.6	H14A—C14—H14C	109.5
C3—C2—H2B	108.6	H14B—C14—H14C	109.5
H2A—C2—H2B	107.6	C3—C15—H15A	109.5
C2—C3—C14	109.80 (16)	C3—C15—H15B	109.5
C2—C3—C4	107.99 (13)	H15A—C15—H15B	109.5
C14—C3—C4	110.11 (16)	C3—C15—H15C	109.5
C2—C3—C15	110.20 (16)	H15A—C15—H15C	109.5
C14—C3—C15	109.71 (16)	H15B—C15—H15C	109.5
C4—C3—C15	109.01 (15)	C8—C16—H16A	109.5
C5—C4—C3	111.64 (13)	C8—C16—H16B	109.5
C5—C4—H4A	109.3	H16A—C16—H16B	109.5
C3—C4—H4A	109.3	C8—C16—H16C	109.5
C5—C4—H4B	109.3	H16A—C16—H16C	109.5
C3—C4—H4B	109.3	H16B—C16—H16C	109.5
H4A—C4—H4B	108.0	C8—C17—H17A	109.5
C13—C5—O1	122.54 (12)	C8—C17—H17B	109.5
C13—C5—C4	125.35 (13)	H17A—C17—H17B	109.5
O1—C5—C4	112.10 (12)	C8—C17—H17C	109.5
C11—C6—O1	123.10 (12)	H17A—C17—H17C	109.5
C11—C6—C7	125.02 (13)	H17B—C17—H17C	109.5
O1—C6—C7	111.87 (12)	C19—C18—C26	119.28 (12)
C6—C7—C8	111.87 (13)	C19—C18—C12	122.19 (12)
C6—C7—H7A	109.2	C26—C18—C12	118.51 (11)
C8—C7—H7A	109.2	C18—C19—C20	122.73 (13)
C6—C7—H7B	109.2	C18—C19—H19	118.6
C8—C7—H7B	109.2	C20—C19—H19	118.6
H7A—C7—H7B	107.9	C25—C20—C21	118.64 (13)
C9—C8—C16	109.92 (16)	C25—C20—C19	117.87 (11)
C9—C8—C7	107.91 (14)	C21—C20—C19	123.49 (13)
C16—C8—C7	110.10 (15)	C22—C21—C20	120.65 (14)
C9—C8—C17	109.80 (16)	C22—C21—H21	119.7
C16—C8—C17	109.99 (16)	C20—C21—H21	119.7
C7—C8—C17	109.08 (15)	C21—C22—C23	119.91 (14)
C10—C9—C8	114.67 (14)	C21—C22—H22	120.0
C10—C9—H9A	108.6	C23—C22—H22	120.0
C8—C9—H9A	108.6	C24—C23—C22	121.51 (14)
C10—C9—H9B	108.6	C24—C23—H23	119.2
C8—C9—H9B	108.6	C22—C23—H23	119.2
H9A—C9—H9B	107.6	C23—C24—C25	118.67 (15)
O3—C10—C11	120.48 (15)	C23—C24—H24	120.7
O3—C10—C9	121.79 (15)	C25—C24—H24	120.7
C11—C10—C9	117.72 (14)	N1—C25—C24	120.91 (13)
C6—C11—C10	119.25 (13)	N1—C25—C20	118.47 (12)
C6—C11—C12	121.96 (12)	C24—C25—C20	120.61 (12)
C10—C11—C12	118.73 (12)	O4—C26—N1	120.18 (12)
C13—C12—C11	109.22 (11)	O4—C26—C18	123.49 (12)
C13—C12—C18	112.13 (11)	N1—C26—C18	116.33 (11)
C11—C12—C18	110.82 (11)	C26—N1—C25	125.29 (12)
C13—C12—H12	108.2	C26—N1—H1	117.4
C11—C12—H12	108.2	C25—N1—H1	117.4
C18—C12—H12	108.2	C6—O1—C5	117.90 (11)
C5—C13—C1	118.88 (13)
O2—C1—C2—C3	154.25 (16)	O2—C1—C13—C12	−5.0 (2)
C13—C1—C2—C3	−27.4 (2)	C2—C1—C13—C12	176.67 (13)
C1—C2—C3—C14	−67.12 (18)	C11—C12—C13—C5	−16.39 (18)
C1—C2—C3—C4	52.96 (18)	C18—C12—C13—C5	106.85 (14)
C1—C2—C3—C15	171.93 (15)	C11—C12—C13—C1	164.79 (12)
C2—C3—C4—C5	−50.47 (19)	C18—C12—C13—C1	−71.97 (16)
C14—C3—C4—C5	69.4 (2)	C13—C12—C18—C19	119.75 (14)
C15—C3—C4—C5	−170.19 (16)	C11—C12—C18—C19	−117.92 (14)
C3—C4—C5—C13	24.7 (2)	C13—C12—C18—C26	−61.91 (16)
C3—C4—C5—O1	−155.28 (14)	C11—C12—C18—C26	60.42 (16)
C11—C6—C7—C8	−24.0 (2)	C26—C18—C19—C20	−1.0 (2)
O1—C6—C7—C8	154.99 (14)	C12—C18—C19—C20	177.32 (12)
C6—C7—C8—C9	50.08 (19)	C18—C19—C20—C25	−0.5 (2)
C6—C7—C8—C16	−69.9 (2)	C18—C19—C20—C21	179.66 (14)
C6—C7—C8—C17	169.32 (17)	C25—C20—C21—C22	−0.8 (2)
C16—C8—C9—C10	67.51 (19)	C19—C20—C21—C22	179.00 (14)
C7—C8—C9—C10	−52.6 (2)	C20—C21—C22—C23	0.3 (2)
C17—C8—C9—C10	−171.36 (16)	C21—C22—C23—C24	0.1 (3)
C8—C9—C10—O3	−154.44 (17)	C22—C23—C24—C25	0.0 (3)
C8—C9—C10—C11	26.8 (2)	C23—C24—C25—N1	179.22 (15)
O1—C6—C11—C10	176.71 (13)	C23—C24—C25—C20	−0.6 (2)
C7—C6—C11—C10	−4.4 (2)	C21—C20—C25—N1	−178.84 (12)
O1—C6—C11—C12	−6.2 (2)	C19—C20—C25—N1	1.33 (19)
C7—C6—C11—C12	172.67 (14)	C21—C20—C25—C24	1.0 (2)
O3—C10—C11—C6	−175.50 (15)	C19—C20—C25—C24	−178.87 (13)
C9—C10—C11—C6	3.2 (2)	C19—C18—C26—O4	−178.65 (14)
O3—C10—C11—C12	7.3 (2)	C12—C18—C26—O4	3.0 (2)
C9—C10—C11—C12	−173.96 (13)	C19—C18—C26—N1	1.7 (2)
C6—C11—C12—C13	17.21 (17)	C12—C18—C26—N1	−176.69 (12)
C10—C11—C12—C13	−165.68 (12)	O4—C26—N1—C25	179.42 (13)
C6—C11—C12—C18	−106.80 (14)	C18—C26—N1—C25	−0.9 (2)
C10—C11—C12—C18	70.31 (16)	C24—C25—N1—C26	179.59 (15)
O1—C5—C13—C1	−176.73 (13)	C20—C25—N1—C26	−0.6 (2)
C4—C5—C13—C1	3.3 (2)	C11—C6—O1—C5	−8.0 (2)
O1—C5—C13—C12	4.5 (2)	C7—C6—O1—C5	173.06 (12)
C4—C5—C13—C12	−175.55 (13)	C13—C5—O1—C6	8.8 (2)
O2—C1—C13—C5	176.14 (15)	C4—C5—O1—C6	−171.17 (12)
C2—C1—C13—C5	−2.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	1.93	2.787 (2)	176
C22—H22···O1^ii	0.93	2.55	3.320 (2)	140

Symmetry codes: (i) −x+3/2, −y+1/2, z; (ii) x, y−1, z.