9-(2-Chloro­phen­yl)-1,2,3,4,5,6,7,8,9,10-deca­hydro-3,3,6,6-tetra­methyl­acridine-1,8-dione

The title compound, C₂₃H₂₆ClNO₂, was synthesized by the reaction of 5,5-dimethyl­cyclo­hexane-1,3-dione with 4-chloro-N-(2-chloro­benzyl­idene)benzenamine under solvent-free conditions using triethylbenzylammonium chloride as catalyst at 353 K. The dihydro­pyridine ring of the mol­ecule adopts a half-chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.078
• wR factor = 0.269
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.269
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.123
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C1      ..       6.95 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C13     ..       5.89 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C23 H26 Cl N O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 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
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

9-(2-Chlorophenyl)-1,2,3,4,5,6,7,8,9,10-decahydro-3,3,6,6-tetramethylacridine- 1,8-dione

Crystal data

C23H26ClNO2	F(000) = 1632
Mr = 383.90	Dx = 1.301 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.004 (6) Å	Cell parameters from 1635 reflections
b = 11.429 (4) Å	θ = 2.2–19.7°
c = 21.741 (10) Å	µ = 0.21 mm^−1
β = 111.858 (15)°	T = 298 K
V = 3921 (3) Å^3	Block, colourless
Z = 8	0.24 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3463 independent reflections
Radiation source: fine-focus sealed tube	1617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.123
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→20
Tmin = 0.951, Tmax = 0.973	k = −8→13
9874 measured reflections	l = −25→24

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.269	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 19.16P] where P = (Fo^2 + 2Fc^2)/3
3463 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.49 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
Cl1	0.26172 (12)	0.4759 (2)	1.35968 (11)	0.0907 (8)
O1	0.4513 (3)	0.4715 (4)	1.3342 (2)	0.0654 (13)
O2	0.3175 (3)	0.6233 (4)	1.5024 (2)	0.0629 (13)
N1	0.5817 (2)	0.7395 (4)	1.5044 (2)	0.0327 (11)
H1	0.6262	0.7810	1.5242	0.039*
C1	0.5773 (3)	0.6712 (5)	1.4524 (3)	0.0454 (15)
C2	0.6563 (3)	0.6726 (6)	1.4396 (3)	0.0521 (17)
H2A	0.6952	0.6157	1.4682	0.063*
H2B	0.6823	0.7492	1.4507	0.063*
C3	0.6424 (3)	0.6449 (5)	1.3678 (3)	0.0462 (15)
C4	0.5893 (4)	0.5335 (5)	1.3488 (3)	0.0500 (16)
H4A	0.5731	0.5207	1.3016	0.060*
H4B	0.6242	0.4679	1.3715	0.060*
C5	0.5106 (4)	0.5344 (5)	1.3646 (3)	0.0460 (15)
C6	0.5080 (3)	0.6091 (5)	1.4178 (3)	0.0396 (14)
C7	0.4285 (3)	0.6148 (5)	1.4327 (3)	0.0423 (15)
H7	0.4123	0.5349	1.4394	0.051*
C8	0.4446 (3)	0.6826 (5)	1.4950 (3)	0.0418 (14)
C9	0.3797 (4)	0.6855 (5)	1.5241 (3)	0.0449 (15)
C10	0.3929 (4)	0.7632 (6)	1.5827 (3)	0.0534 (17)
H10A	0.4147	0.7159	1.6226	0.064*
H10B	0.3383	0.7938	1.5796	0.064*
C11	0.4530 (4)	0.8656 (6)	1.5901 (3)	0.0497 (16)
C12	0.5332 (4)	0.8174 (6)	1.5843 (3)	0.0527 (17)
H12A	0.5690	0.8820	1.5821	0.063*
H12B	0.5640	0.7722	1.6237	0.063*
C13	0.5155 (4)	0.7423 (5)	1.5251 (3)	0.0467 (15)
C14	0.7275 (4)	0.6248 (7)	1.3623 (4)	0.069 (2)
H14A	0.7560	0.5611	1.3906	0.103*
H14B	0.7613	0.6944	1.3755	0.103*
H14C	0.7192	0.6062	1.3173	0.103*
C15	0.5977 (4)	0.7448 (6)	1.3233 (4)	0.071 (2)
H15A	0.5435	0.7572	1.3265	0.107*
H15B	0.5899	0.7262	1.2783	0.107*
H15C	0.6313	0.8144	1.3367	0.107*
C16	0.4121 (4)	0.9561 (6)	1.5376 (4)	0.070 (2)
H16A	0.3614	0.9845	1.5422	0.104*
H16B	0.3981	0.9217	1.4946	0.104*
H16C	0.4506	1.0200	1.5427	0.104*
C17	0.4754 (4)	0.9213 (7)	1.6582 (3)	0.067 (2)
H17A	0.5009	0.8636	1.6919	0.100*
H17B	0.4249	0.9508	1.6625	0.100*
H17C	0.5145	0.9844	1.6631	0.100*
C18	0.3564 (3)	0.6693 (6)	1.3765 (3)	0.0451 (15)
C19	0.2804 (4)	0.6170 (7)	1.3426 (3)	0.0597 (19)
C20	0.2156 (4)	0.6740 (10)	1.2927 (4)	0.081 (3)
H20	0.1646	0.6363	1.2699	0.097*
C21	0.2284 (6)	0.7876 (10)	1.2777 (4)	0.087 (3)
H21	0.1851	0.8274	1.2450	0.105*
C22	0.3031 (5)	0.8424 (8)	1.3099 (4)	0.074 (2)
H22	0.3109	0.9189	1.2989	0.089*
C23	0.3670 (4)	0.7856 (6)	1.3585 (3)	0.0598 (18)
H23	0.4182	0.8238	1.3802	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0845 (14)	0.0872 (16)	0.1029 (16)	−0.0444 (12)	0.0378 (12)	−0.0333 (13)
O1	0.061 (3)	0.064 (3)	0.073 (3)	−0.021 (3)	0.028 (2)	−0.029 (3)
O2	0.057 (3)	0.074 (3)	0.061 (3)	−0.020 (3)	0.025 (2)	−0.012 (3)
N1	0.023 (2)	0.038 (3)	0.035 (2)	−0.0111 (19)	0.0085 (18)	−0.018 (2)
C1	0.043 (3)	0.043 (4)	0.046 (4)	−0.002 (3)	0.011 (3)	0.004 (3)
C2	0.037 (3)	0.057 (4)	0.060 (4)	−0.001 (3)	0.015 (3)	−0.014 (3)
C3	0.038 (3)	0.047 (4)	0.052 (4)	0.000 (3)	0.016 (3)	0.001 (3)
C4	0.057 (4)	0.048 (4)	0.049 (4)	−0.003 (3)	0.024 (3)	−0.001 (3)
C5	0.048 (4)	0.041 (4)	0.046 (4)	−0.001 (3)	0.015 (3)	−0.002 (3)
C6	0.042 (3)	0.037 (3)	0.040 (3)	−0.003 (3)	0.016 (3)	−0.003 (3)
C7	0.042 (3)	0.036 (3)	0.047 (4)	−0.010 (3)	0.014 (3)	0.001 (3)
C8	0.047 (3)	0.041 (3)	0.037 (3)	−0.002 (3)	0.015 (3)	−0.001 (3)
C9	0.051 (4)	0.043 (4)	0.042 (3)	−0.001 (3)	0.019 (3)	0.005 (3)
C10	0.069 (4)	0.053 (4)	0.048 (4)	−0.006 (3)	0.032 (3)	−0.004 (3)
C11	0.055 (4)	0.049 (4)	0.048 (4)	−0.003 (3)	0.023 (3)	−0.005 (3)
C12	0.054 (4)	0.059 (4)	0.044 (4)	−0.009 (3)	0.017 (3)	−0.009 (3)
C13	0.051 (4)	0.045 (4)	0.040 (3)	0.001 (3)	0.013 (3)	−0.004 (3)
C14	0.061 (4)	0.076 (5)	0.078 (5)	−0.011 (4)	0.035 (4)	−0.019 (4)
C15	0.068 (4)	0.060 (5)	0.086 (5)	−0.005 (4)	0.029 (4)	0.018 (4)
C16	0.084 (5)	0.050 (4)	0.081 (5)	0.009 (4)	0.038 (4)	0.005 (4)
C17	0.078 (5)	0.067 (5)	0.059 (4)	−0.010 (4)	0.029 (4)	−0.018 (4)
C18	0.047 (3)	0.049 (4)	0.040 (3)	−0.003 (3)	0.018 (3)	−0.007 (3)
C19	0.052 (4)	0.077 (5)	0.054 (4)	−0.009 (4)	0.023 (3)	−0.014 (4)
C20	0.050 (4)	0.140 (9)	0.049 (4)	0.000 (5)	0.013 (3)	−0.016 (5)
C21	0.077 (6)	0.136 (9)	0.048 (5)	0.035 (6)	0.024 (4)	0.011 (6)
C22	0.085 (5)	0.079 (6)	0.058 (5)	0.029 (5)	0.026 (4)	0.011 (4)
C23	0.076 (4)	0.063 (5)	0.042 (4)	0.019 (4)	0.023 (3)	0.004 (4)

Geometric parameters (Å, º)

Cl1—C19	1.711 (8)	C11—C16	1.504 (9)
O1—C5	1.214 (7)	C11—C12	1.519 (8)
O2—C9	1.214 (7)	C11—C17	1.524 (8)
N1—C1	1.353 (7)	C12—C13	1.482 (8)
N1—C13	1.360 (7)	C12—H12A	0.9700
N1—H1	0.8600	C12—H12B	0.9700
C1—C6	1.340 (7)	C14—H14A	0.9600
C1—C2	1.470 (7)	C14—H14B	0.9600
C2—C3	1.522 (8)	C14—H14C	0.9600
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C3—C15	1.507 (8)	C15—H15C	0.9600
C3—C14	1.514 (8)	C16—H16A	0.9600
C3—C4	1.526 (8)	C16—H16B	0.9600
C4—C5	1.500 (8)	C16—H16C	0.9600
C4—H4A	0.9700	C17—H17A	0.9600
C4—H4B	0.9700	C17—H17B	0.9600
C5—C6	1.451 (8)	C17—H17C	0.9600
C6—C7	1.506 (7)	C18—C19	1.365 (8)
C7—C8	1.494 (7)	C18—C23	1.416 (9)
C7—C18	1.506 (7)	C19—C20	1.387 (10)
C7—H7	0.9800	C20—C21	1.375 (12)
C8—C13	1.326 (8)	C20—H20	0.9300
C8—C9	1.461 (8)	C21—C22	1.354 (11)
C9—C10	1.500 (8)	C21—H21	0.9300
C10—C11	1.523 (8)	C22—C23	1.365 (9)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—H23	0.9300
C1—N1—C13	119.6 (5)	C10—C11—C17	109.7 (5)
C1—N1—H1	120.2	C13—C12—C11	112.6 (5)
C13—N1—H1	120.2	C13—C12—H12A	109.1
C6—C1—N1	122.6 (5)	C11—C12—H12A	109.1
C6—C1—C2	125.0 (6)	C13—C12—H12B	109.1
N1—C1—C2	112.4 (5)	C11—C12—H12B	109.1
C1—C2—C3	112.8 (5)	H12A—C12—H12B	107.8
C1—C2—H2A	109.0	C8—C13—N1	122.5 (5)
C3—C2—H2A	109.0	C8—C13—C12	125.4 (6)
C1—C2—H2B	109.0	N1—C13—C12	112.0 (5)
C3—C2—H2B	109.0	C3—C14—H14A	109.5
H2A—C2—H2B	107.8	C3—C14—H14B	109.5
C15—C3—C14	109.4 (5)	H14A—C14—H14B	109.5
C15—C3—C2	110.5 (5)	C3—C14—H14C	109.5
C14—C3—C2	108.9 (5)	H14A—C14—H14C	109.5
C15—C3—C4	110.6 (5)	H14B—C14—H14C	109.5
C14—C3—C4	109.8 (5)	C3—C15—H15A	109.5
C2—C3—C4	107.6 (5)	C3—C15—H15B	109.5
C5—C4—C3	114.8 (5)	H15A—C15—H15B	109.5
C5—C4—H4A	108.6	C3—C15—H15C	109.5
C3—C4—H4A	108.6	H15A—C15—H15C	109.5
C5—C4—H4B	108.6	H15B—C15—H15C	109.5
C3—C4—H4B	108.6	C11—C16—H16A	109.5
H4A—C4—H4B	107.5	C11—C16—H16B	109.5
O1—C5—C6	121.1 (5)	H16A—C16—H16B	109.5
O1—C5—C4	120.2 (6)	C11—C16—H16C	109.5
C6—C5—C4	118.7 (5)	H16A—C16—H16C	109.5
C1—C6—C5	118.6 (5)	H16B—C16—H16C	109.5
C1—C6—C7	121.9 (5)	C11—C17—H17A	109.5
C5—C6—C7	119.6 (5)	C11—C17—H17B	109.5
C8—C7—C6	110.0 (4)	H17A—C17—H17B	109.5
C8—C7—C18	109.9 (5)	C11—C17—H17C	109.5
C6—C7—C18	111.6 (5)	H17A—C17—H17C	109.5
C8—C7—H7	108.4	H17B—C17—H17C	109.5
C6—C7—H7	108.4	C19—C18—C23	117.0 (6)
C18—C7—H7	108.4	C19—C18—C7	125.3 (6)
C13—C8—C9	118.0 (5)	C23—C18—C7	117.6 (5)
C13—C8—C7	122.6 (5)	C18—C19—C20	122.2 (7)
C9—C8—C7	119.4 (5)	C18—C19—Cl1	120.7 (5)
O2—C9—C8	120.5 (6)	C20—C19—Cl1	117.1 (6)
O2—C9—C10	120.6 (5)	C21—C20—C19	118.6 (8)
C8—C9—C10	118.9 (5)	C21—C20—H20	120.7
C9—C10—C11	115.2 (5)	C19—C20—H20	120.7
C9—C10—H10A	108.5	C22—C21—C20	121.0 (8)
C11—C10—H10A	108.5	C22—C21—H21	119.5
C9—C10—H10B	108.5	C20—C21—H21	119.5
C11—C10—H10B	108.5	C21—C22—C23	120.2 (8)
H10A—C10—H10B	107.5	C21—C22—H22	119.9
C16—C11—C12	111.3 (5)	C23—C22—H22	119.9
C16—C11—C10	110.3 (5)	C22—C23—C18	120.9 (7)
C12—C11—C10	107.5 (5)	C22—C23—H23	119.5
C16—C11—C17	109.1 (6)	C18—C23—H23	119.5
C12—C11—C17	108.9 (5)