Crystal structure of 2-[4-(4-chloro­phen­yl)-1-(4-meth­oxy­phen­yl)-2-oxoazetidin-3-yl]benzo[de]iso­quinoline-1,3-dione dimethyl sulfoxide monosolvate

Çelik, Í.; Akkurt, M.; Jarrahpour, A.; Rad, J.A.; Çelik, Ö.

doi:10.1107/S2056989015001425

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o129-o130

doi:10.1107/S2056989015001425

Open

access

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik,^a Mehmet Akkurt,^b ^* Aliasghar Jarrahpour,^c Javad Ameri Rad ^c and Ömer Çelik ^d,^e

^aDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 06532 Sivas, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, ^dDepartment of Physics, Faculty of Education, Dicle University, 21280, Diyarbakir, Turkey, and ^eScience and Technology Application and Research Center, Dicle University, 21280, Diyarbakir, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 January 2015; accepted 22 January 2015; online 28 January 2015)

In the title solvated compound, C₂₈H₁₉N₂O₄·C₂H₆OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C—H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C—H⋯O hydrogen bonds, C—H⋯π interactions and aromatic π–π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Keywords: crystal structure; β-lactam ring; 1H-benzo[de]isoquinoline-1,3(2H)-dione group; disorder; azetidin-2-ones.

CCDC reference: 1044874

1. Related literature

For general background to β-lactams, see: Alcaide & Almendros (2004 ); Alcala et al. (2011 ); Li et al. (2011 ); Long & Turos (2002 ); MacIntyre et al. (2010 ); Rogers & Kelly (1999 ); Sawa et al. (2006 ); Southgate (1994 ); Zhang & Zhou (2011 ); Zhang et al. (2011 ). For related structures, see: Atioğlu et al. (2014 ); Butcher et al. (2011 ); Jarrahpour et al. (2012 ); Zarei (2013 ).

2. Experimental

2.1. Crystal data

C₂₈H₁₉ClN₂O₄·C₂H₆OS
M_r = 561.03
Triclinic, $[P \overline 1]$
a = 7.9925 (3) Å
b = 12.1761 (5) Å
c = 14.2313 (6) Å
α = 93.549 (2)°
β = 95.520 (2)°
γ = 101.602 (2)°
V = 1345.67 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.45 × 0.30 × 0.20 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
29975 measured reflections
7737 independent reflections
5777 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.191
S = 1.05
7737 reflections
359 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11–C16 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.57	3.169 (3)	122
C21—H21⋯O1ⁱ	0.93	2.52	3.344 (2)	148
C25—H25⋯O4ⁱⁱ	0.93	2.46	3.221 (2)	139
C30A—H30A⋯Cg4ⁱⁱⁱ	0.96	2.88	3.818 (10)	167
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1044874

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015001425/hb7354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015001425/hb7354Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015001425/hb7354Isup3.cml

checkCIF report

Comment top

Even more than 70 years after the discovery of penicillin, β-lactam antibiotics remain as one of the most important contributions of science to humanity (Southgate, 1994) and the β-lactam antibiotics have served as a powerful line of defense against bacterial infections (Long, et al., 2002). They have also been used as synthons for the synthesis of various natural and unnatural products (Alcaide & Almendros, 2004). On the other hand, cyclic imides have received special attraction due to their widely potential pharmaceutical applications (Zhang & Zhou, 2011). Isoquinolindione (naphthalimide) derivatives are cyclic imides to be of interest due to their useful photophysical and biological properties that offer promise for medical applications as free radical scavengers (Zhang, et al., 2011), potential photoredox anticancer agents (MacIntyre, et al., 2010), fluorescent labels (Sawa, et al., 2006), photosensitizers (Rogers & Kelly, 1999) and imaging agents (Alcala et al., 2011). Many of these properties are related to 1,8- naphthalimides planar shape and optimal size that makes them efficient DNA intercalating agents with high antitumor activity (Li et al., 2011; Zarei, 2013).

In the title compound (Fig. 1), the β-lactam ring (N1/C1–C3) is nearly planar [r.m.s. deviation = 0.002 Å]. It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy and choloro phenyl rings (C4–C9 and C11–C16) and the ring plane (N2/C17–C28) of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group which is nearly planar [max. deviations = -0.089 (1) Å for N2 and 0.044 (2) Å for C24], respectively.

All bond lengths and bond angles are normal and comparable with those reported for related compounds (Butcher et al., 2011; Atioğlu et al., 2014; Jarrahpour et al., 2012).

Molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal, molecules are linked by intermolecular C—H···O hydrogen bonds, forming three dimensional network (Table 1, Figs. 2 & 3).

Furthermore, one weak C—H···π interaction (Table 1) and π-π stacking interactions [Cg2···Cg6 (2 - x,1 - y,-z) = 3.6166 (10) Å and Cg5···Cg6(2 - x,1 - y,-z) = 3.7159 (10) Å; where Cg2, Cg5 and Cg6 are centroids of the N2/C17/C18/C23/C24/C28 central pyridine ring and the C18–C23 and C22—C27 benzene rings of the 1H-benzo[de]isoquinoline-1,3(2H)-dione group, respectively] also partially take part in the stabilization of the structure.

Related literature top

For general background to β-lactams, see: Alcaide & Almendros (2004); Alcala et al. (2011); Li et al. (2011); Long & Turos (2002); MacIntyre et al. (2010); Rogers & Kelly (1999); Sawa et al. (2006); Southgate (1994); Zhang & Zhou (2011); Zhang et al. (2011). For related structures, see: Atioğlu et al. (2014); Butcher et al. (2011); Jarrahpour et al. (2012); Zarei (2013).

Experimental top

4-Chlorophenyl-N-(4-methoxyphenyl)methanimine (1 mmol), triethylamine (5 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetic acid (1.50 mmol) and tosyl chloride (1.50 mmol) were added to anhydrous CH₂Cl₂ (5 ml) and the mixture was stirred at room temperature for 24 h. The mixture was washed with HCl 1 N (2×20 ml), saturated aqueous NaHCO₃ solution (50 ml) and brine (20 ml). The organic layer was dried (Na₂SO₄) and the solvent was removed to give the product as a white solid·It was then purified by recrystallization from DMSO to afford colourless triclinic crystals (Yield 75%); Mp: 528–530 K; IR (KBr, cm^-1): 1774 (CO β-lactam),1704 (CO Naph), 1666 (CO Naph); ¹H-NMR (250 MHz, DMSO-d₆) δ 1.27 (CH₃ t, 3H, J = 6.75), 3.95 (CH₂ q, 2H, J = 6.75), 5.69 (CH β-lactam d, 1H, J = 2.75), 5.94 (CH β-lactam d, 1H, J = 2.75), 6.91 (aromat d, 2H, J = 9.00), 7.19 (aromat d, 2H, J = 9.00), 7.79–7.89 (ArH, m, 4H), 8.24 (aromat d, 2H, J = 9.00), 8.43–8.50 (ArH, m, 4H); ¹³C-NMR (62 MHz, DMSO-d₆) δ 163.22 (CO β-lactam), 162.13 (CO Naph), 155.04, 147.47, 144.82, 134.88, 131.22, 131.17, 130.50, 128.10, 127.43, 127.30, 123.95, 121.54, 118.29, 115.04, (aromatic carbons), 63.41 (C β-lactam), 63.19 (C β-lactam), 58.08 (CH₂—O), 14.56 (CH₃); GC—MS m/z = 507 [M+].

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the molecular structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 30% probability level. Only the major component of the disordered solvent molecule is displayed.
	Fig. 2. The hydrogen bonding and molecular packing of the title compound along a axis. Only the major component of the disordered solvent molecule is displayed.
	Fig. 3. The hydrogen bonding and molecular packing of the title compound along c axis. Only the major component of the disordered solvent molecule is displayed.

2-[2-(4-Chlorophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate top

Crystal data top

C₂₈H₁₉ClN₂O₄·C₂H₆OS	Z = 2
M_r = 561.03	F(000) = 584
Triclinic, P1	D_x = 1.385 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9925 (3) Å	Cell parameters from 9923 reflections
b = 12.1761 (5) Å	θ = 2.9–29.9°
c = 14.2313 (6) Å	µ = 0.26 mm⁻¹
α = 93.549 (2)°	T = 296 K
β = 95.520 (2)°	Prism, colourless
γ = 101.602 (2)°	0.45 × 0.30 × 0.20 mm
V = 1345.67 (9) Å³

Data collection top

Bruker APEXII CCD diffractometer	5777 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 30.0°, θ_min = 2.2°
ϕ and ω scans	h = −11→11
29975 measured reflections	k = −17→17
7737 independent reflections	l = −19→19

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.191	w = 1/[σ²(F_o²) + (0.0977P)² + 0.5061P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
7737 reflections	Δρ_max = 0.68 e Å⁻³
359 parameters	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₈H₁₉ClN₂O₄·C₂H₆OS	γ = 101.602 (2)°
M_r = 561.03	V = 1345.67 (9) Å³
Triclinic, P1	Z = 2
a = 7.9925 (3) Å	Mo Kα radiation
b = 12.1761 (5) Å	µ = 0.26 mm⁻¹
c = 14.2313 (6) Å	T = 296 K
α = 93.549 (2)°	0.45 × 0.30 × 0.20 mm
β = 95.520 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5777 reflections with I > 2σ(I)
29975 measured reflections	R_int = 0.022
7737 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	6 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.05	Δρ_max = 0.68 e Å⁻³
7737 reflections	Δρ_min = −0.52 e Å⁻³
359 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
Cl1	0.69679 (12)	0.13588 (7)	0.68363 (4)	0.0886 (3)
S1A	0.83996 (15)	0.62942 (10)	0.36822 (7)	0.0884 (4)	0.847 (2)
S1B	0.7471 (8)	0.6453 (5)	0.4182 (4)	0.0884 (4)	0.153 (2)
O1	0.5935 (2)	0.15324 (13)	0.07604 (10)	0.0572 (5)
O2	−0.20212 (18)	−0.02113 (14)	0.22243 (12)	0.0620 (5)
O3	1.06205 (19)	0.37028 (13)	0.29270 (12)	0.0603 (5)
O4	0.58077 (15)	0.40773 (12)	0.11511 (10)	0.0467 (4)
N1	0.48129 (19)	0.18953 (13)	0.21909 (10)	0.0411 (4)
N2	0.82660 (17)	0.38087 (12)	0.19376 (10)	0.0355 (4)
C1	0.5863 (2)	0.27720 (14)	0.28906 (12)	0.0368 (5)
C2	0.7342 (2)	0.27719 (14)	0.22466 (12)	0.0381 (5)
C3	0.5985 (2)	0.19748 (15)	0.15453 (13)	0.0423 (5)
C4	0.3093 (2)	0.13255 (14)	0.21725 (12)	0.0372 (5)
C5	0.2294 (3)	0.05633 (17)	0.14244 (13)	0.0469 (6)
O5A	0.6596 (5)	0.5604 (2)	0.3457 (2)	0.1081 (11)	0.847 (2)
C6	0.0575 (3)	0.00331 (17)	0.14164 (14)	0.0497 (6)
C7	−0.0327 (2)	0.02482 (16)	0.21594 (14)	0.0450 (5)
C8	0.0494 (2)	0.09910 (18)	0.29171 (15)	0.0488 (6)
C9	0.2184 (2)	0.15335 (16)	0.29214 (14)	0.0450 (6)
C10	−0.2998 (3)	−0.0868 (2)	0.1422 (2)	0.0750 (9)
C11	0.6159 (2)	0.24211 (14)	0.38776 (12)	0.0365 (4)
C12	0.6490 (2)	0.13637 (15)	0.40284 (13)	0.0413 (5)
C13	0.6763 (3)	0.10452 (17)	0.49434 (14)	0.0477 (6)
C14	0.6676 (3)	0.17782 (19)	0.56949 (14)	0.0524 (6)
C15	0.6345 (4)	0.2827 (2)	0.55697 (15)	0.0612 (8)
C16	0.6094 (3)	0.31440 (17)	0.46505 (14)	0.0500 (6)
C17	1.0008 (2)	0.41714 (14)	0.22957 (12)	0.0376 (5)
C18	1.1000 (2)	0.51167 (13)	0.18560 (11)	0.0337 (4)
C19	1.2760 (2)	0.54014 (16)	0.20663 (13)	0.0428 (5)
C20	1.3723 (2)	0.62737 (18)	0.16236 (15)	0.0495 (6)
C21	1.2935 (2)	0.68586 (17)	0.09901 (13)	0.0464 (5)
C22	1.1127 (2)	0.66006 (14)	0.07639 (12)	0.0372 (5)
C23	1.01511 (19)	0.56994 (13)	0.11954 (10)	0.0316 (4)
C24	0.83533 (19)	0.53926 (13)	0.09505 (11)	0.0325 (4)
C25	0.7550 (2)	0.59720 (15)	0.03094 (12)	0.0393 (5)
C26	0.8512 (3)	0.68702 (16)	−0.01091 (13)	0.0462 (6)
C27	1.0259 (3)	0.71740 (15)	0.01086 (13)	0.0438 (5)
C28	0.7350 (2)	0.44063 (14)	0.13389 (11)	0.0341 (4)
O5B	0.688 (3)	0.6029 (15)	0.3255 (13)	0.1081 (11)	0.153 (2)
C29A	0.8342 (10)	0.7606 (7)	0.3416 (6)	0.183 (3)	0.847 (2)
C30A	0.8821 (12)	0.6486 (7)	0.4874 (7)	0.183 (3)	0.847 (2)
C29B	0.821 (6)	0.786 (2)	0.413 (4)	0.183 (3)	0.153 (2)
C30B	0.904 (5)	0.593 (4)	0.479 (5)	0.183 (3)	0.153 (2)
H1	0.54490	0.34770	0.28880	0.0440*
H2	0.81630	0.23530	0.25290	0.0460*
H5	0.29030	0.04040	0.09260	0.0560*
H6	0.00350	−0.04690	0.09060	0.0600*
H8	−0.01000	0.11250	0.34290	0.0580*
H9	0.27160	0.20410	0.34290	0.0540*
H10A	−0.41530	−0.11360	0.15630	0.1130*
H10B	−0.30120	−0.04140	0.08940	0.1130*
H10C	−0.24890	−0.14960	0.12670	0.1130*
H12	0.65280	0.08650	0.35130	0.0500*
H13	0.70030	0.03420	0.50420	0.0570*
H15	0.62890	0.33170	0.60890	0.0730*
H16	0.58800	0.38550	0.45580	0.0600*
H19	1.33080	0.50150	0.25020	0.0510*
H20	1.49120	0.64560	0.17630	0.0590*
H21	1.35960	0.74340	0.07030	0.0560*
H25	0.63660	0.57680	0.01530	0.0470*
H26	0.79580	0.72620	−0.05380	0.0550*
H27	1.08800	0.77660	−0.01790	0.0530*
H29A	0.94730	0.80710	0.35510	0.2740*	0.847 (2)
H29B	0.79540	0.76000	0.27560	0.2740*	0.847 (2)
H29C	0.75680	0.78990	0.37900	0.2740*	0.847 (2)
H30A	0.99640	0.69240	0.50420	0.2740*	0.847 (2)
H30B	0.80100	0.68750	0.51270	0.2740*	0.847 (2)
H30C	0.87290	0.57690	0.51320	0.2740*	0.847 (2)
H29D	0.86430	0.82040	0.47590	0.2740*	0.153 (2)
H29E	0.91190	0.79800	0.37310	0.2740*	0.153 (2)
H29F	0.72910	0.81960	0.38830	0.2740*	0.153 (2)
H30D	0.93010	0.63100	0.54170	0.2740*	0.153 (2)
H30E	0.86390	0.51410	0.48360	0.2740*	0.153 (2)
H30F	1.00470	0.60530	0.44680	0.2740*	0.153 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1404 (7)	0.0971 (5)	0.0389 (3)	0.0438 (5)	0.0117 (3)	0.0232 (3)
S1A	0.0995 (7)	0.1062 (7)	0.0621 (5)	0.0320 (6)	0.0056 (4)	−0.0015 (5)
S1B	0.0995 (7)	0.1062 (7)	0.0621 (5)	0.0320 (6)	0.0056 (4)	−0.0015 (5)
O1	0.0713 (10)	0.0540 (8)	0.0402 (7)	−0.0060 (7)	0.0177 (7)	0.0018 (6)
O2	0.0407 (7)	0.0676 (10)	0.0676 (10)	−0.0074 (7)	0.0065 (7)	−0.0120 (8)
O3	0.0527 (8)	0.0609 (9)	0.0618 (9)	0.0030 (7)	−0.0159 (7)	0.0261 (7)
O4	0.0309 (6)	0.0547 (8)	0.0505 (7)	−0.0006 (5)	−0.0019 (5)	0.0152 (6)
N1	0.0403 (7)	0.0450 (8)	0.0327 (7)	−0.0041 (6)	0.0042 (5)	0.0040 (6)
N2	0.0317 (6)	0.0381 (7)	0.0354 (7)	0.0019 (5)	0.0032 (5)	0.0111 (5)
C1	0.0355 (8)	0.0394 (8)	0.0328 (8)	0.0009 (6)	0.0036 (6)	0.0058 (6)
C2	0.0381 (8)	0.0385 (8)	0.0369 (8)	0.0030 (6)	0.0065 (6)	0.0104 (6)
C3	0.0478 (9)	0.0399 (8)	0.0368 (9)	0.0002 (7)	0.0085 (7)	0.0083 (7)
C4	0.0378 (8)	0.0368 (8)	0.0353 (8)	0.0027 (6)	0.0020 (6)	0.0091 (6)
C5	0.0503 (10)	0.0490 (10)	0.0361 (9)	−0.0030 (8)	0.0077 (7)	0.0025 (7)
O5A	0.128 (2)	0.0609 (17)	0.112 (2)	−0.0059 (18)	−0.0486 (19)	0.0060 (15)
C6	0.0515 (10)	0.0459 (10)	0.0431 (10)	−0.0064 (8)	0.0025 (8)	−0.0035 (8)
C7	0.0393 (9)	0.0410 (9)	0.0508 (10)	0.0012 (7)	0.0023 (7)	0.0009 (7)
C8	0.0377 (9)	0.0554 (11)	0.0507 (11)	0.0063 (8)	0.0067 (7)	−0.0065 (8)
C9	0.0383 (9)	0.0486 (10)	0.0440 (10)	0.0051 (7)	−0.0001 (7)	−0.0077 (8)
C10	0.0529 (13)	0.0739 (16)	0.0820 (18)	−0.0143 (11)	0.0018 (12)	−0.0205 (13)
C11	0.0332 (7)	0.0404 (8)	0.0335 (8)	0.0008 (6)	0.0045 (6)	0.0061 (6)
C12	0.0458 (9)	0.0401 (8)	0.0376 (9)	0.0059 (7)	0.0084 (7)	0.0044 (7)
C13	0.0555 (11)	0.0449 (9)	0.0448 (10)	0.0109 (8)	0.0092 (8)	0.0122 (8)
C14	0.0626 (12)	0.0604 (12)	0.0352 (9)	0.0123 (9)	0.0059 (8)	0.0120 (8)
C15	0.0901 (17)	0.0599 (13)	0.0355 (10)	0.0227 (12)	0.0047 (10)	−0.0008 (9)
C16	0.0686 (13)	0.0423 (9)	0.0395 (10)	0.0142 (9)	0.0025 (8)	0.0031 (7)
C17	0.0347 (8)	0.0404 (8)	0.0358 (8)	0.0052 (6)	−0.0021 (6)	0.0056 (6)
C18	0.0310 (7)	0.0361 (7)	0.0313 (7)	0.0025 (6)	0.0011 (5)	−0.0008 (6)
C19	0.0334 (8)	0.0491 (9)	0.0418 (9)	0.0044 (7)	−0.0029 (6)	−0.0031 (7)
C20	0.0315 (8)	0.0594 (11)	0.0495 (10)	−0.0059 (7)	0.0027 (7)	−0.0061 (8)
C21	0.0417 (9)	0.0475 (9)	0.0417 (9)	−0.0108 (7)	0.0095 (7)	−0.0029 (7)
C22	0.0416 (8)	0.0344 (8)	0.0316 (8)	−0.0019 (6)	0.0076 (6)	−0.0016 (6)
C23	0.0324 (7)	0.0323 (7)	0.0276 (7)	0.0017 (5)	0.0037 (5)	−0.0009 (5)
C24	0.0326 (7)	0.0341 (7)	0.0296 (7)	0.0037 (6)	0.0029 (5)	0.0039 (6)
C25	0.0399 (8)	0.0411 (8)	0.0361 (8)	0.0083 (7)	−0.0003 (6)	0.0057 (7)
C26	0.0590 (11)	0.0409 (9)	0.0401 (9)	0.0130 (8)	0.0031 (8)	0.0106 (7)
C27	0.0561 (10)	0.0345 (8)	0.0382 (9)	−0.0002 (7)	0.0105 (7)	0.0060 (7)
C28	0.0310 (7)	0.0389 (8)	0.0312 (7)	0.0040 (6)	0.0020 (5)	0.0069 (6)
O5B	0.128 (2)	0.0609 (17)	0.112 (2)	−0.0059 (18)	−0.0486 (19)	0.0060 (15)
C29A	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C30A	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C29B	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)
C30B	0.140 (4)	0.184 (6)	0.187 (5)	−0.034 (4)	−0.060 (4)	0.058 (5)

Geometric parameters (Å, º) top

Cl1—C14	1.741 (2)	C22—C23	1.422 (2)
S1A—C30A	1.689 (10)	C22—C27	1.411 (3)
S1A—O5A	1.509 (4)	C23—C24	1.413 (2)
S1A—C29A	1.673 (8)	C24—C25	1.375 (2)
S1B—O5B	1.388 (19)	C24—C28	1.473 (2)
S1B—C30B	1.71 (5)	C25—C26	1.405 (3)
S1B—C29B	1.71 (3)	C26—C27	1.370 (3)
O1—C3	1.203 (2)	C1—H1	0.9800
O2—C10	1.420 (3)	C2—H2	0.9800
O2—C7	1.371 (2)	C5—H5	0.9300
O3—C17	1.210 (2)	C6—H6	0.9300
O4—C28	1.215 (2)	C8—H8	0.9300
N1—C3	1.368 (2)	C9—H9	0.9300
N1—C1	1.477 (2)	C10—H10C	0.9600
N1—C4	1.407 (2)	C10—H10B	0.9600
N2—C28	1.401 (2)	C10—H10A	0.9600
N2—C2	1.445 (2)	C12—H12	0.9300
N2—C17	1.408 (2)	C13—H13	0.9300
C1—C2	1.564 (2)	C15—H15	0.9300
C1—C11	1.504 (2)	C16—H16	0.9300
C2—C3	1.537 (2)	C19—H19	0.9300
C4—C5	1.382 (3)	C20—H20	0.9300
C4—C9	1.385 (2)	C21—H21	0.9300
C5—C6	1.394 (3)	C25—H25	0.9300
C6—C7	1.377 (3)	C26—H26	0.9300
C7—C8	1.384 (3)	C27—H27	0.9300
C8—C9	1.378 (2)	C29A—H29C	0.9600
C11—C12	1.391 (2)	C29A—H29A	0.9600
C11—C16	1.377 (3)	C29A—H29B	0.9600
C12—C13	1.391 (3)	C30A—H30A	0.9600
C13—C14	1.366 (3)	C30A—H30B	0.9600
C14—C15	1.374 (3)	C30A—H30C	0.9600
C15—C16	1.394 (3)	C29B—H29D	0.9700
C17—C18	1.471 (2)	C29B—H29E	0.9600
C18—C23	1.415 (2)	C29B—H29F	0.9600
C18—C19	1.378 (2)	C30B—H30D	0.9600
C19—C20	1.402 (3)	C30B—H30E	0.9600
C20—C21	1.367 (3)	C30B—H30F	0.9500
C21—C22	1.416 (2)

O5A—S1A—C30A	107.4 (3)	O4—C28—N2	119.23 (15)
C29A—S1A—C30A	100.9 (4)	N1—C1—H1	112.00
O5A—S1A—C29A	107.1 (3)	C11—C1—H1	112.00
C29B—S1B—C30B	108 (2)	C2—C1—H1	112.00
O5B—S1B—C29B	106 (2)	C3—C2—H2	110.00
O5B—S1B—C30B	119 (2)	N2—C2—H2	109.00
C7—O2—C10	118.08 (18)	C1—C2—H2	109.00
C3—N1—C4	133.80 (15)	C6—C5—H5	120.00
C1—N1—C4	129.79 (14)	C4—C5—H5	120.00
C1—N1—C3	95.78 (14)	C7—C6—H6	120.00
C2—N2—C17	117.44 (14)	C5—C6—H6	120.00
C17—N2—C28	124.63 (14)	C7—C8—H8	120.00
C2—N2—C28	117.87 (14)	C9—C8—H8	120.00
N1—C1—C11	115.59 (14)	C4—C9—H9	120.00
N1—C1—C2	86.20 (12)	C8—C9—H9	120.00
C2—C1—C11	117.03 (14)	O2—C10—H10C	109.00
C1—C2—C3	85.86 (12)	O2—C10—H10B	109.00
N2—C2—C1	120.95 (14)	H10A—C10—H10C	110.00
N2—C2—C3	119.42 (14)	O2—C10—H10A	109.00
O1—C3—N1	132.51 (17)	H10A—C10—H10B	109.00
N1—C3—C2	91.20 (14)	H10B—C10—H10C	109.00
O1—C3—C2	136.20 (17)	C11—C12—H12	120.00
N1—C4—C9	119.16 (15)	C13—C12—H12	120.00
C5—C4—C9	119.41 (17)	C14—C13—H13	120.00
N1—C4—C5	121.44 (16)	C12—C13—H13	120.00
C4—C5—C6	120.03 (19)	C14—C15—H15	121.00
C5—C6—C7	120.34 (18)	C16—C15—H15	121.00
O2—C7—C8	115.19 (17)	C11—C16—H16	120.00
C6—C7—C8	119.29 (17)	C15—C16—H16	119.00
O2—C7—C6	125.52 (18)	C20—C19—H19	120.00
C7—C8—C9	120.65 (18)	C18—C19—H19	120.00
C4—C9—C8	120.25 (18)	C21—C20—H20	120.00
C12—C11—C16	118.78 (17)	C19—C20—H20	120.00
C1—C11—C16	120.29 (16)	C22—C21—H21	120.00
C1—C11—C12	120.93 (15)	C20—C21—H21	120.00
C11—C12—C13	120.60 (17)	C26—C25—H25	120.00
C12—C13—C14	119.18 (19)	C24—C25—H25	120.00
C13—C14—C15	121.63 (19)	C27—C26—H26	120.00
Cl1—C14—C13	118.83 (17)	C25—C26—H26	120.00
Cl1—C14—C15	119.53 (16)	C22—C27—H27	120.00
C14—C15—C16	118.8 (2)	C26—C27—H27	120.00
C11—C16—C15	121.02 (19)	S1A—C29A—H29B	109.00
O3—C17—C18	123.36 (16)	H29A—C29A—H29C	109.00
O3—C17—N2	120.05 (16)	S1A—C29A—H29C	109.00
N2—C17—C18	116.58 (14)	H29A—C29A—H29B	110.00
C17—C18—C19	119.58 (15)	S1A—C29A—H29A	109.00
C17—C18—C23	119.88 (14)	H29B—C29A—H29C	110.00
C19—C18—C23	120.51 (15)	S1A—C30A—H30C	110.00
C18—C19—C20	119.98 (16)	H30A—C30A—H30C	109.00
C19—C20—C21	120.76 (16)	H30B—C30A—H30C	109.00
C20—C21—C22	120.96 (17)	H30A—C30A—H30B	109.00
C21—C22—C27	122.97 (17)	S1A—C30A—H30A	110.00
C23—C22—C27	118.61 (16)	S1A—C30A—H30B	109.00
C21—C22—C23	118.39 (15)	S1B—C29B—H29D	109.00
C22—C23—C24	119.53 (14)	S1B—C29B—H29E	110.00
C18—C23—C24	121.09 (14)	S1B—C29B—H29F	110.00
C18—C23—C22	119.37 (14)	H29D—C29B—H29E	109.00
C23—C24—C25	120.25 (15)	H29D—C29B—H29F	109.00
C25—C24—C28	119.77 (14)	H29E—C29B—H29F	110.00
C23—C24—C28	119.88 (14)	S1B—C30B—H30D	109.00
C24—C25—C26	120.21 (16)	S1B—C30B—H30E	109.00
C25—C26—C27	120.58 (18)	S1B—C30B—H30F	110.00
C22—C27—C26	120.81 (17)	H30D—C30B—H30E	109.00
N2—C28—C24	116.85 (14)	H30D—C30B—H30F	110.00
O4—C28—C24	123.89 (15)	H30E—C30B—H30F	110.00

C10—O2—C7—C6	−7.4 (3)	C6—C7—C8—C9	1.6 (3)
C10—O2—C7—C8	172.23 (19)	O2—C7—C8—C9	−178.04 (18)
C3—N1—C1—C2	−7.68 (13)	C7—C8—C9—C4	−1.2 (3)
C4—N1—C1—C11	62.4 (2)	C1—C11—C12—C13	180.00 (18)
C4—N1—C1—C2	−179.39 (17)	C16—C11—C12—C13	−0.5 (3)
C3—N1—C1—C11	−125.92 (15)	C12—C11—C16—C15	−0.3 (3)
C4—N1—C3—O1	−4.1 (4)	C1—C11—C16—C15	179.2 (2)
C1—N1—C3—C2	7.80 (14)	C11—C12—C13—C14	1.0 (3)
C4—N1—C3—C2	178.97 (19)	C12—C13—C14—C15	−0.8 (4)
C1—N1—C4—C5	176.58 (17)	C12—C13—C14—Cl1	178.46 (17)
C3—N1—C4—C5	8.0 (3)	Cl1—C14—C15—C16	−179.2 (2)
C1—N1—C4—C9	−3.5 (3)	C13—C14—C15—C16	0.0 (4)
C3—N1—C4—C9	−172.02 (19)	C14—C15—C16—C11	0.6 (4)
C1—N1—C3—O1	−175.3 (2)	O3—C17—C18—C19	9.3 (3)
C17—N2—C2—C3	−143.50 (15)	N2—C17—C18—C23	7.7 (2)
C28—N2—C2—C3	39.3 (2)	O3—C17—C18—C23	−173.05 (17)
C28—N2—C17—C18	−13.0 (2)	N2—C17—C18—C19	−169.99 (15)
C28—N2—C2—C1	−64.7 (2)	C17—C18—C23—C22	−179.03 (15)
C2—N2—C28—O4	4.7 (2)	C19—C18—C23—C24	177.96 (15)
C2—N2—C17—O3	−9.2 (2)	C17—C18—C23—C24	0.3 (2)
C17—N2—C28—O4	−172.28 (16)	C19—C18—C23—C22	−1.4 (2)
C28—N2—C17—O3	167.75 (17)	C23—C18—C19—C20	−0.1 (3)
C2—N2—C17—C18	170.06 (14)	C17—C18—C19—C20	177.60 (17)
C2—N2—C28—C24	−173.56 (14)	C18—C19—C20—C21	0.8 (3)
C17—N2—C2—C1	112.52 (17)	C19—C20—C21—C22	0.0 (3)
C17—N2—C28—C24	9.5 (2)	C20—C21—C22—C23	−1.5 (3)
N1—C1—C11—C16	−139.21 (18)	C20—C21—C22—C27	−179.41 (18)
N1—C1—C11—C12	40.3 (2)	C21—C22—C23—C24	−177.24 (15)
C2—C1—C11—C16	121.47 (19)	C27—C22—C23—C18	−179.85 (15)
C11—C1—C2—C3	123.69 (15)	C21—C22—C23—C18	2.1 (2)
N1—C1—C2—C3	6.81 (12)	C23—C22—C27—C26	0.0 (3)
C11—C1—C2—N2	−114.25 (17)	C27—C22—C23—C24	0.8 (2)
C2—C1—C11—C12	−59.0 (2)	C21—C22—C27—C26	177.94 (18)
N1—C1—C2—N2	128.87 (15)	C18—C23—C24—C28	−3.9 (2)
C1—C2—C3—O1	175.9 (2)	C22—C23—C24—C25	−0.9 (2)
N2—C2—C3—N1	−130.79 (15)	C22—C23—C24—C28	175.38 (14)
N2—C2—C3—O1	52.5 (3)	C18—C23—C24—C25	179.75 (15)
C1—C2—C3—N1	−7.35 (13)	C23—C24—C25—C26	0.2 (2)
C5—C4—C9—C8	−0.5 (3)	C25—C24—C28—N2	175.73 (15)
N1—C4—C9—C8	179.60 (17)	C23—C24—C28—O4	−178.75 (16)
C9—C4—C5—C6	1.6 (3)	C23—C24—C28—N2	−0.6 (2)
N1—C4—C5—C6	−178.42 (18)	C28—C24—C25—C26	−176.07 (16)
C4—C5—C6—C7	−1.2 (3)	C25—C24—C28—O4	−2.4 (3)
C5—C6—C7—O2	179.20 (19)	C24—C25—C26—C27	0.6 (3)
C5—C6—C7—C8	−0.4 (3)	C25—C26—C27—C22	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C11–C16 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.57	3.169 (3)	122
C21—H21···O1ⁱ	0.93	2.52	3.344 (2)	148
C25—H25···O4ⁱⁱ	0.93	2.46	3.221 (2)	139
C30A—H30A···Cg4ⁱⁱⁱ	0.96	2.88	3.818 (10)	167

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C11–C16 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.57	3.169 (3)	122
C21—H21···O1ⁱ	0.93	2.52	3.344 (2)	148
C25—H25···O4ⁱⁱ	0.93	2.46	3.221 (2)	139
C30A—H30A···Cg4ⁱⁱⁱ	0.96	2.88	3.818 (10)	167

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

Acknowledgements

The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and JAR thank the Shiraz University Research Council for financial support (grant No. 93-GR–SC-23).

References

Alcaide, B. & Almendros, P. (2004). Curr. Med. Chem. 11, 1921–1949. Web of Science CrossRef PubMed CAS Google Scholar
Alcala, M. A., Kwan, S. Y., Shade, C. M., Lang, M., Uh, H., Wang, M., Weber, S. G., Bartlett, D. L., Petoud, S. & Lee, Y. J. (2011). Nanomedicine: Nanotechnol. Biol. Med. 7, 249–258. Google Scholar
Atioğlu, Z., Akkurt, M., Jarrahpour, A., Heiran, R. & Özdemir, N. (2014). Acta Cryst. E70, o835–o836. CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Akkurt, M., Jarrahpour, A. & Badrabady, S. A. T. (2011). Acta Cryst. E67, o1101–o1102. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jarrahpour, A., Ebrahimi, E., Khalifeh, R., Sharghi, H., Sahraei, M., Sinou, V., Latour, C. & Brunel, J. M. (2012). Tetrahedron, 68, 4740–4744. Web of Science CrossRef CAS Google Scholar
Li, X. L., Lin, Y. J., Wang, Q. Q., Yuan, Y. K., Zhang, H. & Qian, X. H. (2011). Eur. J. Med. Chem. 46, 1274–1279. Google Scholar
Long, T. E. & Turos, E. (2002). Curr. Med. Chem. Anti-infective Agents, 1, 251–268. Google Scholar
MacIntyre, M. M., Martell, J. M. & Eriksson, L. A. (2010). J. Mol. Struct. Theochem, 941, 133–137. Google Scholar
Rogers, J. E. & Kelly, L. A. (1999). J. Am. Chem. Soc. 121, 3854–3861. Google Scholar
Sawa, M., Hsu, T. L., Itoh, T., Sugiyama, M., Hanson, S. R., Vogt, P. K. & Wong, C. H. (2006). Proc. Natl Acad. Sci. USA, 103, 12371–12376. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Southgate, R. (1994). Contemp. Org. Synth. 1, 417–431. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zarei, M. (2013). Tetrahedron, 69, 6620–6626. Google Scholar
Zhang, Y., Feng, S., Wu, Q., Wang, K., Yi, X., Wang, H. & Pan, Y. (2011). Med. Chem. Res. 20, 752–759. Google Scholar
Zhang, Y.-Y. & Zhou, Ch.-H. (2011). Bioorg. Med. Chem. Lett. 21, 4349–4352. 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 71| Part 2| February 2015| Pages o129-o130

doi:10.1107/S2056989015001425

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

Crystal structure of 2-[4-(4-chloro­phen­yl)-1-(4-meth­­oxy­phen­yl)-2-oxoazetidin-3-yl]benzo[de]iso­quinoline-1,3-dione di­methyl sulfoxide monosolvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvate