(2RS,5′RS)-3′,4′-Bis(4-chloro­phen­yl)-3,4-dihydro­spiro­[acridine-2,5′(4′H)-[1,2]oxazol]-1(2H)-one

Narayanan, P.; Maheswari, S.U.; Sethusankar, K.

doi:10.1107/S1600536812045084

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3289

doi:10.1107/S1600536812045084

Open

access

(2RS,5′RS)-3′,4′-Bis(4-chlorophenyl)-3,4-dihydrospiro[acridine-2,5′(4′H)-[1,2]oxazol]-1(2H)-one

Ponmudisettu Narayanan,^a Shanmugavel Uma Maheswari ^b and Krishnan Sethusankar ^a ^*

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Chemistry, School of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 25 September 2012; accepted 31 October 2012; online 7 November 2012)

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 methylene C atom adjacent to the spiro center deviating by 0.289 (2) Å from the mean plane of the remaining atoms. In the crystal, molecules are linked via C—H⋯Cl interactions and C—Cl⋯O halogen bonds [2.958 (2) Å, 171.39 (7)°], which generate bifurcated R₂¹(6) ring motifs resulting in C₂¹[R₂¹(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_r = 473.33
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.143
S = 1.02
5960 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.66 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812045084/ld2076sup1.cif

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

checkCIF report

Comment top

Acridine derivatives are biologically important compounds, which are found to possess mutagenic, antitumour (Talacki et al., 1974), antibacterial, antiamoebic, hypersensitive, antiinflammatory and antiimplantation (Asthana et al., 1991) activities. Also, they have been shown to exert toxicity towards plasmodium, trypanosoma and leishmania parasites (Di Giorgio et al., 2005). Against this backround, X-ray study of the title compound has been carried out to study its structural aspects.

The title compound C₂₇ H₁₈ Cl₂ N₂ O₂, consists of an isoxazole ring spiro attached to acridine ring system and the phenyl rings (C22–C27) and (C16–C21). X-ray analysis confirms the molecular stereochemistry as illustrated in Fig. 1. The quinoline ring system is essentially planar with a maximum deviation of -0.049 (2) Å for C9 atom. The quinoline ring system forms a dihedral angle of 86.12 (10) ° with the chlorophenyl ring (C16–C21), which shows that they are almost orthogonal to each other. The chlorophenyl ring (C22–C27) forms a dihedral angle of 74.99 (9) ° with the quinoline ring system.

The six membered carbocyclic ring (C8–C13) adopts a sofa conformation with the deviation of C11 by -0.289 (2) Å from the mean plane formed by the remaining ring atoms. The mean plane of the six membered ring (C8–C13) forms a dihedral angle of 85.34 (11) ° with the chlorophenyl ring (C16–C21), which shows that they are almost perpendicular to each other. The oxygen atom (O1) significantly deviates from the mean plane of the ring (C8–C13) by -0.3368 (18) Å. The mean plane of the six membered carbocyclic ring (C8–C13) forms a dihedral angle of 2.53 (8) ° with the quinoline ring system, which shows that they are almost coplanar.

The isoxazole ring (N2/O2/C12/C14/C15) adopts an envelope conformation with a maximum deviation of C12 by 0.0935 (18) Å from the mean plane formed by the remaining ring atoms. The isoxazole ring forms the dihedral angles of 82.77 (8) °, 83.52 (9) ° and 83.45 (10) ° with the quinoline bicyclic ring system, the six membered ring (C8–C13) and the phenyl ring (C22–C27), respectively. The chlorine atoms (Cl1 & Cl2) are significantly deviate from the phenyl ring (C16–C21) and (C22–C27) by -0.0113 (19) Å and 0.0666 (8) Å, respectively. The title compound exhibits structural similarities with already reported related structures (Sridharan et al., 2009; Trzybiński et al., 2010).

In the crystal, the molecules are linked via C10—H10A···Cl2ⁱ intermolecular interaction and C25ⁱ—Cl2ⁱ···O2 halogen bonding (XB), between the chlorine atom(Cl2) and keto group oxygen atom(O2) of the acridine ring system [Cl2ⁱ···O2 = 2.958 (2) Å and a nearly linear C25ⁱ—Cl2ⁱ···O2 angle of 171.39 (7) °], which generate bifurcated R₂¹(6) ring motifs resulting in chains with the full graph-set designation of C₂¹[R₂¹(6)] running parallel to [0 1 0] axis. (Bernstein et al., 1995) (Fig. 2). The symmetry code: (i). 3/2 - x,-1/2 + y,1/2 - z

Related literature top

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 top

A mixture of 3,4-dihydroacridin-1(2H)-one(200 mg, 1 mmol), 4-chloro benzaldehyde (168 mg, 1.2 mmol) and KOH (84 mg, 1.5 mmol) in DME (3 ml) was stirred at ambient temperature for 30 min. Then, 4-chloro-N-hydroxybenzimi doyl chloride (285 mg, 1.5 mmol) was added subsequently to the reaction mixture and stirred at room temperature for 10–12 h. The progress of the reaction was monitored by thin-layer chromatography with petroleum ether-ethylacetate (4:1 v/v) mixture as eluent. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (2x20 ml), washed with water (2x10 ml), dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The residue thus obtained recrystallized from diethyl-ether to afford (2S,3'S)-3',4'-bis(4-chlorophenyl)-3,4-dihydro-1H,3'H-spiro[acridine-2,2'-[1,5]oxazole]-1-one as off white solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.

Yield = 89%,

m.p. = 214–216 °C.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at 30% probability level.

Fig. 2. The crystal packing of the title compound, viewed along c-axis, showing bifurcated bonding including Cl2: C10—H10A···Cl2ⁱ hydrogen bonds and C25ⁱ—Cl2ⁱ···O2 halogen bonds, resulting into supramolecular chains C¹₂[R¹₂(6)] running parallel to [0 1 0] direction. The hydrogen atoms not involved in the hydrogen bonding have been excluded for clarity. The symmetry code: (i). 3/2 - x,-1/2 + y,1/2 - z.

(2RS,5'RS)-3',4'-Bis(4-chlorophenyl)-3,4- dihydrospiro[acridine-2,5'(4'H)-[1,2]oxazol]-1(2H)-one top

Crystal data top

C₂₇H₁₈Cl₂N₂O₂	F(000) = 976
M_r = 473.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.055P)² + 1.1784P] where P = (F_o² + 2F_c²)/3
5960 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₂₇H₁₈Cl₂N₂O₂	V = 2258.24 (18) Å³
M_r = 473.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6493 (4) Å	µ = 0.32 mm⁻¹
b = 15.1553 (7) Å	T = 293 K
c = 19.4802 (8) Å	0.35 × 0.30 × 0.25 mm
β = 90.392 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5960 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4189 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.924	R_int = 0.026
26147 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
5960 reflections	Δρ_min = −0.66 e Å⁻³
298 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₇H₁₈Cl₂N₂O₂
M_r	473.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.6493 (4), 15.1553 (7), 19.4802 (8)
β (°)	90.392 (1)
V (Å³)	2258.24 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.895, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	26147, 5960, 4189
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.143, 1.02
No. of reflections	5960
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.66

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cl2ⁱ	0.97	2.78	3.681 (2)	154.0

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

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

Asthana, P., Rastogi, S., Ghose, S. & Das, S. R. (1991). Indian J. Chem. Sect. B, 30, 893–900. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Di Giorgio, C., De Meo, M., Chiron, J., Delmas, F., Nikoyan, A., Severine, J., Dumenil, G., Timon-David, P. & Galy, J.-P. (2005). Bioorg. Med. Chem. 13, 5560–5568. Web of Science PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridharan, M., Rajendra Prasad, K. J. & Zeller, M. (2009). Acta Cryst. E65, o1064. Web of Science CSD CrossRef IUCr Journals Google Scholar
Talacki, R., Carrell, H. L. & Glusker, J. P. (1974). Acta Cryst. B30, 1044–1047. CSD CrossRef IUCr Journals Web of Science Google Scholar
Trzybiński, D., Zadykowicz, B., Krzymiński, K., Sikorski, A. & Błażejowski, J. (2010). Acta Cryst. E66, o828–o829. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3289

doi:10.1107/S1600536812045084

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2RS,5′RS)-3′,4′-Bis(4-chloro­phen­yl)-3,4-di­hydro­spiro­[acridine-2,5′(4′H)-[1,2]oxazol]-1(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2RS,5′RS)-3′,4′-Bis(4-chlorophenyl)-3,4-dihydrospiro[acridine-2,5′(4′H)-[1,2]oxazol]-1(2H)-one