(2RS,5'RS)-3',4'-Bis(4-chloro-phen-yl)-3,4-dihydro-spiro-[acridine-2,5'(4'H)-[1,2]oxazol]-1(2H)-one.

The title compound, C27H18Cl2N2O2, represents a racemic mixture of the corresponding R,R and S,S diastereomers. The isoxazoline ring adopts an envelope conformation with the spiro C atom deviating by 0.093 (2) Å from the rest of the ring. The six-membered keto-substituted carbocycle has a sofa conformation with the methyl-ene C atom adjacent to the spiro center deviating by 0.289 (2) Å from the mean plane of the remaining atoms. In the crystal, mol-ecules are linked via C-H⋯Cl inter-actions and C-Cl⋯O halogen bonds [2.958 (2) Å, 171.39 (7)°], which generate bifurcated R2(1)(6) ring motifs resulting in C2(1)[R2(1)(6)] chains running parallel to [010].

Related literature

For the uses and biological importance of acridines, see: Asthana et al. (1991 ▶); Di Giorgio et al. (2005 ▶); Talacki et al. (1974 ▶). For related structures, see: Sridharan et al. (2009 ▶); Trzybiński et al. (2010 ▶). For graph-set notation, see: Bernstein et al.(1995 ▶)

Experimental

Crystal data

C27H18Cl2N2O2

M = 473.33

Monoclinic,

a = 7.6493 (4) Å

b = 15.1553 (7) Å

c = 19.4802 (8) Å

β = 90.392 (1)°

V = 2258.24 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.895, T max = 0.924

26147 measured reflections

5960 independent reflections

4189 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.143

S = 1.02

5960 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045084/ld2076sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045084/ld2076Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H18Cl2N2O2	F(000) = 976
Mr = 473.33	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5960 reflections
a = 7.6493 (4) Å	θ = 2.5–29.1°
b = 15.1553 (7) Å	µ = 0.32 mm−1
c = 19.4802 (8) Å	T = 293 K
β = 90.392 (1)°	Block, colourless
V = 2258.24 (18) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5960 independent reflections
Radiation source: fine-focus sealed tube	4189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 29.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→8
Tmin = 0.895, Tmax = 0.924	k = −19→20
26147 measured reflections	l = −26→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.055P)2 + 1.1784P] where P = (Fo2 + 2Fc2)/3
5960 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0838 (3)	0.35507 (15)	0.51570 (10)	0.0529 (5)
C2	0.0846 (4)	0.30775 (17)	0.57843 (12)	0.0673 (7)
H2	0.1872	0.3031	0.6041	0.081*
C3	−0.0648 (4)	0.26917 (18)	0.60111 (13)	0.0744 (8)
H3	−0.0624	0.2371	0.6418	0.089*
C4	−0.2209 (4)	0.27669 (17)	0.56474 (14)	0.0713 (8)
H4	−0.3214	0.2498	0.5814	0.086*
C5	−0.2280 (4)	0.32318 (16)	0.50486 (13)	0.0645 (6)
H5	−0.3332	0.3283	0.4809	0.077*
C6	−0.0756 (3)	0.36356 (14)	0.47927 (11)	0.0514 (5)
C7	−0.0714 (3)	0.41213 (14)	0.41763 (11)	0.0487 (5)
H7	−0.1739	0.4215	0.3928	0.058*
C8	0.0829 (3)	0.44546 (13)	0.39442 (9)	0.0412 (4)
C9	0.2379 (3)	0.43039 (14)	0.43295 (9)	0.0447 (5)
C10	0.4114 (3)	0.45889 (15)	0.40672 (10)	0.0500 (5)
H10A	0.4716	0.4077	0.3886	0.060*
H10B	0.4804	0.4812	0.4449	0.060*
C11	0.4037 (3)	0.52926 (14)	0.35131 (10)	0.0467 (5)
H11A	0.3775	0.5857	0.3723	0.056*
H11B	0.5173	0.5339	0.3298	0.056*
C12	0.2668 (2)	0.50947 (12)	0.29669 (9)	0.0370 (4)
C13	0.0870 (3)	0.49484 (13)	0.32843 (9)	0.0403 (4)
C14	0.2591 (2)	0.57197 (12)	0.23452 (9)	0.0368 (4)
H14	0.1517	0.6072	0.2358	0.044*
C15	0.2486 (2)	0.50547 (12)	0.17730 (9)	0.0387 (4)
C16	0.2293 (3)	0.52867 (13)	0.10425 (10)	0.0438 (4)
C17	0.2685 (4)	0.46792 (16)	0.05371 (11)	0.0595 (6)
H17	0.3050	0.4116	0.0662	0.071*
C18	0.2543 (4)	0.48944 (18)	−0.01475 (11)	0.0668 (7)
H18	0.2803	0.4480	−0.0484	0.080*
C19	0.2013 (3)	0.57288 (18)	−0.03267 (11)	0.0604 (6)
C20	0.1643 (3)	0.63492 (18)	0.01599 (12)	0.0635 (6)
H20	0.1302	0.6914	0.0030	0.076*
C21	0.1782 (3)	0.61285 (16)	0.08492 (11)	0.0545 (5)
H21	0.1530	0.6547	0.1183	0.065*
C22	0.4159 (2)	0.63149 (12)	0.22639 (9)	0.0380 (4)
C23	0.4050 (3)	0.72015 (13)	0.24167 (10)	0.0449 (4)
H23	0.2985	0.7442	0.2548	0.054*
C24	0.5513 (3)	0.77360 (14)	0.23758 (11)	0.0528 (5)
H24	0.5440	0.8334	0.2479	0.063*
C25	0.7065 (3)	0.73722 (16)	0.21810 (11)	0.0532 (6)
C26	0.7203 (3)	0.64889 (16)	0.20123 (12)	0.0561 (6)
H26	0.8266	0.6253	0.1874	0.067*
C27	0.5743 (3)	0.59690 (14)	0.20536 (11)	0.0488 (5)
H27	0.5817	0.5375	0.1939	0.059*
N1	0.2385 (3)	0.38799 (13)	0.49232 (8)	0.0536 (5)
N2	0.2748 (2)	0.42569 (11)	0.19573 (8)	0.0430 (4)
O1	−0.0456 (2)	0.51723 (12)	0.29909 (8)	0.0617 (4)
O2	0.30472 (18)	0.42271 (8)	0.26726 (6)	0.0424 (3)
Cl1	0.18361 (12)	0.59980 (6)	−0.11902 (3)	0.0901 (3)
Cl2	0.89238 (10)	0.80315 (5)	0.21560 (4)	0.0828 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0719 (15)	0.0483 (12)	0.0386 (10)	0.0143 (10)	0.0080 (10)	0.0029 (8)
C2	0.091 (2)	0.0665 (16)	0.0440 (11)	0.0183 (14)	0.0048 (12)	0.0111 (11)
C3	0.109 (2)	0.0636 (16)	0.0510 (13)	0.0186 (15)	0.0246 (15)	0.0167 (11)
C4	0.090 (2)	0.0566 (15)	0.0682 (16)	0.0104 (14)	0.0296 (15)	0.0166 (12)
C5	0.0696 (16)	0.0603 (15)	0.0638 (14)	0.0094 (12)	0.0178 (12)	0.0145 (11)
C6	0.0639 (14)	0.0440 (11)	0.0464 (10)	0.0117 (10)	0.0131 (10)	0.0054 (9)
C7	0.0501 (12)	0.0489 (12)	0.0471 (10)	0.0093 (9)	0.0046 (9)	0.0078 (9)
C8	0.0470 (11)	0.0410 (10)	0.0355 (8)	0.0083 (8)	0.0027 (8)	0.0008 (7)
C9	0.0520 (12)	0.0475 (11)	0.0345 (9)	0.0096 (9)	−0.0014 (8)	−0.0033 (8)
C10	0.0476 (12)	0.0667 (14)	0.0355 (9)	0.0069 (10)	−0.0093 (8)	−0.0007 (9)
C11	0.0443 (11)	0.0532 (12)	0.0424 (10)	−0.0016 (9)	−0.0057 (8)	−0.0032 (9)
C12	0.0387 (10)	0.0352 (9)	0.0369 (8)	0.0038 (7)	−0.0024 (7)	−0.0002 (7)
C13	0.0415 (11)	0.0414 (10)	0.0381 (9)	0.0043 (8)	−0.0010 (8)	0.0022 (7)
C14	0.0356 (10)	0.0346 (9)	0.0400 (9)	0.0017 (7)	−0.0016 (7)	0.0009 (7)
C15	0.0395 (10)	0.0386 (10)	0.0379 (9)	−0.0043 (8)	−0.0016 (7)	0.0009 (7)
C16	0.0460 (11)	0.0468 (11)	0.0385 (9)	−0.0093 (9)	−0.0029 (8)	0.0045 (8)
C17	0.0833 (18)	0.0516 (13)	0.0435 (11)	−0.0079 (12)	−0.0013 (11)	0.0003 (9)
C18	0.0899 (19)	0.0700 (16)	0.0403 (11)	−0.0166 (14)	0.0019 (11)	−0.0052 (10)
C19	0.0641 (15)	0.0789 (17)	0.0382 (10)	−0.0215 (13)	−0.0078 (10)	0.0109 (10)
C20	0.0731 (16)	0.0661 (15)	0.0511 (12)	−0.0023 (13)	−0.0066 (11)	0.0175 (11)
C21	0.0635 (14)	0.0571 (13)	0.0430 (10)	0.0016 (11)	−0.0023 (10)	0.0060 (9)
C22	0.0409 (10)	0.0351 (9)	0.0380 (9)	−0.0011 (8)	−0.0025 (7)	0.0016 (7)
C23	0.0503 (12)	0.0382 (10)	0.0462 (10)	0.0016 (8)	−0.0012 (9)	0.0003 (8)
C24	0.0674 (15)	0.0393 (11)	0.0515 (11)	−0.0114 (10)	−0.0097 (10)	0.0036 (9)
C25	0.0511 (13)	0.0591 (14)	0.0491 (11)	−0.0207 (10)	−0.0135 (9)	0.0163 (10)
C26	0.0395 (12)	0.0659 (15)	0.0629 (13)	−0.0025 (10)	0.0002 (10)	0.0089 (11)
C27	0.0432 (11)	0.0414 (11)	0.0617 (12)	0.0006 (9)	0.0020 (9)	−0.0020 (9)
N1	0.0654 (12)	0.0597 (11)	0.0358 (8)	0.0118 (9)	−0.0019 (8)	0.0041 (8)
N2	0.0510 (10)	0.0412 (9)	0.0368 (8)	−0.0002 (7)	−0.0032 (7)	−0.0015 (6)
O1	0.0410 (9)	0.0822 (12)	0.0620 (9)	0.0053 (8)	−0.0031 (7)	0.0296 (8)
O2	0.0531 (8)	0.0377 (7)	0.0365 (6)	0.0092 (6)	−0.0028 (6)	0.0010 (5)
Cl1	0.1173 (7)	0.1131 (6)	0.0398 (3)	−0.0268 (5)	−0.0110 (3)	0.0189 (3)
Cl2	0.0693 (4)	0.0932 (5)	0.0855 (5)	−0.0443 (4)	−0.0209 (4)	0.0288 (4)

C1—N1	1.365 (3)	C14—C15	1.504 (2)
C1—C6	1.413 (3)	C14—C22	1.510 (3)
C1—C2	1.417 (3)	C14—H14	0.9800
C2—C3	1.360 (4)	C15—N2	1.277 (2)
C2—H2	0.9300	C15—C16	1.472 (3)
C3—C4	1.389 (4)	C16—C17	1.382 (3)
C3—H3	0.9300	C16—C21	1.386 (3)
C4—C5	1.363 (3)	C17—C18	1.376 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.411 (3)	C18—C19	1.372 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.409 (3)	C19—C20	1.366 (4)
C7—C8	1.364 (3)	C19—Cl1	1.735 (2)
C7—H7	0.9300	C20—C21	1.387 (3)
C8—C9	1.417 (3)	C20—H20	0.9300
C8—C13	1.488 (3)	C21—H21	0.9300
C9—N1	1.323 (2)	C22—C23	1.379 (3)
C9—C10	1.490 (3)	C22—C27	1.385 (3)
C10—C11	1.518 (3)	C23—C24	1.384 (3)
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700	C24—C25	1.365 (3)
C11—C12	1.518 (3)	C24—H24	0.9300
C11—H11A	0.9700	C25—C26	1.383 (3)
C11—H11B	0.9700	C25—Cl2	1.739 (2)
C12—O2	1.464 (2)	C26—C27	1.370 (3)
C12—C13	1.528 (3)	C26—H26	0.9300
C12—C14	1.538 (2)	C27—H27	0.9300
C13—O1	1.209 (2)	N2—O2	1.4111 (19)
N1—C1—C6	123.12 (18)	C15—C14—C22	111.14 (15)
N1—C1—C2	118.3 (2)	C15—C14—C12	99.93 (14)
C6—C1—C2	118.5 (2)	C22—C14—C12	115.11 (15)
C3—C2—C1	119.9 (3)	C15—C14—H14	110.1
C3—C2—H2	120.0	C22—C14—H14	110.1
C1—C2—H2	120.0	C12—C14—H14	110.1
C2—C3—C4	121.4 (2)	N2—C15—C16	120.84 (17)
C2—C3—H3	119.3	N2—C15—C14	114.74 (16)
C4—C3—H3	119.3	C16—C15—C14	124.10 (16)
C5—C4—C3	120.5 (3)	C17—C16—C21	118.80 (19)
C5—C4—H4	119.7	C17—C16—C15	120.57 (19)
C3—C4—H4	119.7	C21—C16—C15	120.58 (19)
C4—C5—C6	119.9 (3)	C18—C17—C16	121.1 (2)
C4—C5—H5	120.1	C18—C17—H17	119.5
C6—C5—H5	120.1	C16—C17—H17	119.5
C7—C6—C5	123.5 (2)	C19—C18—C17	119.1 (2)
C7—C6—C1	116.8 (2)	C19—C18—H18	120.5
C5—C6—C1	119.7 (2)	C17—C18—H18	120.5
C8—C7—C6	120.1 (2)	C20—C19—C18	121.3 (2)
C8—C7—H7	120.0	C20—C19—Cl1	119.7 (2)
C6—C7—H7	120.0	C18—C19—Cl1	118.9 (2)
C7—C8—C9	119.17 (18)	C19—C20—C21	119.4 (2)
C7—C8—C13	119.74 (18)	C19—C20—H20	120.3
C9—C8—C13	121.07 (18)	C21—C20—H20	120.3
N1—C9—C8	122.6 (2)	C16—C21—C20	120.3 (2)
N1—C9—C10	116.29 (18)	C16—C21—H21	119.9
C8—C9—C10	121.05 (17)	C20—C21—H21	119.9
C9—C10—C11	114.63 (17)	C23—C22—C27	119.15 (19)
C9—C10—H10A	108.6	C23—C22—C14	120.67 (18)
C11—C10—H10A	108.6	C27—C22—C14	120.15 (17)
C9—C10—H10B	108.6	C22—C23—C24	120.5 (2)
C11—C10—H10B	108.6	C22—C23—H23	119.8
H10A—C10—H10B	107.6	C24—C23—H23	119.8
C12—C11—C10	112.53 (17)	C25—C24—C23	119.0 (2)
C12—C11—H11A	109.1	C25—C24—H24	120.5
C10—C11—H11A	109.1	C23—C24—H24	120.5
C12—C11—H11B	109.1	C24—C25—C26	121.7 (2)
C10—C11—H11B	109.1	C24—C25—Cl2	119.25 (19)
H11A—C11—H11B	107.8	C26—C25—Cl2	119.06 (19)
O2—C12—C11	108.33 (15)	C27—C26—C25	118.6 (2)
O2—C12—C13	102.09 (14)	C27—C26—H26	120.7
C11—C12—C13	111.31 (15)	C25—C26—H26	120.7
O2—C12—C14	104.56 (13)	C26—C27—C22	121.0 (2)
C11—C12—C14	116.92 (16)	C26—C27—H27	119.5
C13—C12—C14	112.23 (15)	C22—C27—H27	119.5
O1—C13—C8	121.80 (18)	C9—N1—C1	118.12 (19)
O1—C13—C12	121.48 (17)	C15—N2—O2	109.40 (15)
C8—C13—C12	116.55 (16)	N2—O2—C12	109.06 (12)
N1—C1—C2—C3	−175.8 (2)	C12—C14—C15—N2	−9.7 (2)
C6—C1—C2—C3	2.2 (3)	C22—C14—C15—C16	−61.2 (2)
C1—C2—C3—C4	−1.5 (4)	C12—C14—C15—C16	176.79 (18)
C2—C3—C4—C5	0.1 (4)	N2—C15—C16—C17	−11.1 (3)
C3—C4—C5—C6	0.4 (4)	C14—C15—C16—C17	162.0 (2)
C4—C5—C6—C7	179.5 (2)	N2—C15—C16—C21	171.5 (2)
C4—C5—C6—C1	0.4 (4)	C14—C15—C16—C21	−15.4 (3)
N1—C1—C6—C7	−2.9 (3)	C21—C16—C17—C18	−1.2 (4)
C2—C1—C6—C7	179.1 (2)	C15—C16—C17—C18	−178.6 (2)
N1—C1—C6—C5	176.2 (2)	C16—C17—C18—C19	0.4 (4)
C2—C1—C6—C5	−1.7 (3)	C17—C18—C19—C20	0.7 (4)
C5—C6—C7—C8	−176.7 (2)	C17—C18—C19—Cl1	180.0 (2)
C1—C6—C7—C8	2.5 (3)	C18—C19—C20—C21	−0.9 (4)
C6—C7—C8—C9	0.1 (3)	Cl1—C19—C20—C21	179.79 (19)
C6—C7—C8—C13	178.54 (18)	C17—C16—C21—C20	0.9 (3)
C7—C8—C9—N1	−2.7 (3)	C15—C16—C21—C20	178.4 (2)
C13—C8—C9—N1	178.90 (18)	C19—C20—C21—C16	0.1 (4)
C7—C8—C9—C10	174.79 (19)	C15—C14—C22—C23	141.26 (18)
C13—C8—C9—C10	−3.6 (3)	C12—C14—C22—C23	−106.1 (2)
N1—C9—C10—C11	−162.66 (18)	C15—C14—C22—C27	−40.7 (2)
C8—C9—C10—C11	19.7 (3)	C12—C14—C22—C27	72.0 (2)
C9—C10—C11—C12	−45.5 (2)	C27—C22—C23—C24	−1.4 (3)
C10—C11—C12—O2	−56.8 (2)	C14—C22—C23—C24	176.62 (18)
C10—C11—C12—C13	54.6 (2)	C22—C23—C24—C25	0.1 (3)
C10—C11—C12—C14	−174.55 (16)	C23—C24—C25—C26	1.2 (3)
C7—C8—C13—O1	10.5 (3)	C23—C24—C25—Cl2	−177.88 (16)
C9—C8—C13—O1	−171.1 (2)	C24—C25—C26—C27	−1.0 (3)
C7—C8—C13—C12	−164.82 (18)	Cl2—C25—C26—C27	178.05 (17)
C9—C8—C13—C12	13.6 (3)	C25—C26—C27—C22	−0.4 (3)
O2—C12—C13—O1	−98.6 (2)	C23—C22—C27—C26	1.6 (3)
C11—C12—C13—O1	146.0 (2)	C14—C22—C27—C26	−176.45 (19)
C14—C12—C13—O1	12.8 (3)	C8—C9—N1—C1	2.3 (3)
O2—C12—C13—C8	76.68 (18)	C10—C9—N1—C1	−175.28 (19)
C11—C12—C13—C8	−38.7 (2)	C6—C1—N1—C9	0.6 (3)
C14—C12—C13—C8	−171.91 (16)	C2—C1—N1—C9	178.5 (2)
O2—C12—C14—C15	13.95 (17)	C16—C15—N2—O2	174.59 (16)
C11—C12—C14—C15	133.71 (17)	C14—C15—N2—O2	0.9 (2)
C13—C12—C14—C15	−95.92 (17)	C15—N2—O2—C12	9.2 (2)
O2—C12—C14—C22	−105.16 (17)	C11—C12—O2—N2	−140.22 (15)
C11—C12—C14—C22	14.6 (2)	C13—C12—O2—N2	102.23 (15)
C13—C12—C14—C22	144.98 (16)	C14—C12—O2—N2	−14.85 (18)
C22—C14—C15—N2	112.27 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cl2i	0.97	2.78	3.681 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cl2i	0.97	2.78	3.681 (2)	154

Symmetry code: (i) .