3-(4-Bromo-phen-yl)-1-butyl-5-[1-(2-chloro-6-methyl-phen-yl)-1H-tetra-zol-5-yl]imidazolidine-2,4-dione.

In the title mol-ecule, C21H20BrClN6O2, the chloro-substituted benzene ring forms a dihedral angle of 77.84 (7)° with the tetra-zole ring and the bromo-substituted ring forms a dihedral angle of 43.95 (6)° with the imidazole ring. The dihedral angle between the tetra-zole and imidazole rings is 67.42 (8)°. The terminal methyl group of the butyl substituent is disordered over two sets of sites, with refined occupancies 0.67 (3) and 0.33 (3). In the crystal, there is a short Br⋯N contact of 3.183 (2) Å.

Related literature

For the biological activity of imidazoline-2,4-diones, see: Thenmozhiyal et al. (2004 ▶); Brazil & Pedley (1998 ▶); Luer (1998 ▶); Matzukura et al. (1992 ▶); Knabe et al. (1997 ▶); Somsák et al. (2001 ▶); Moloney et al. (2001 ▶); Moloney et al. (1999 ▶); Sutherland & Hess (2000 ▶). For information on 1-5-disubstituted tetra­zoles. see: Al-Hourani et al. (2011 ▶); Brazil & Pedley (1998 ▶); Davulcu et al. (2009 ▶); Herr (2002 ▶); Quan et al. (2003 ▶); Van Poecke et al. (2011 ▶).

Experimental

Crystal data

C21H20BrClN6O2

M = 503.79

Monoclinic,

a = 27.9412 (9) Å

b = 8.8675 (3) Å

c = 19.6581 (6) Å

β = 112.500 (1)°

V = 4499.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.98 mm−1

T = 100 K

0.36 × 0.2 × 0.03 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.613, T max = 0.746

79112 measured reflections

5647 independent reflections

4475 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.03

5647 reflections

281 parameters

12 restraints

H-atom parameters not refined

Δρmax = 1.34 e Å−3

Δρmin = −1.07 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016000/lh5623sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016000/lh5623Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016000/lh5623Isup3.cml

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

C21H20BrClN6O2	F(000) = 2048
Mr = 503.79	Dx = 1.487 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.9412 (9) Å	Cell parameters from 9862 reflections
b = 8.8675 (3) Å	θ = 2.4–27.9°
c = 19.6581 (6) Å	µ = 1.98 mm−1
β = 112.500 (1)°	T = 100 K
V = 4499.9 (3) Å3	Rectangular, colourless
Z = 8	0.36 × 0.2 × 0.03 mm

Bruker APEXII DUO CCD diffractometer	5647 independent reflections
Radiation source: fine-focus sealed tube	4475 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 28.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→36
Tmin = 0.613, Tmax = 0.746	k = −11→11
79112 measured reflections	l = −26→24

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters not refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0424P)2 + 14.0493P] where P = (Fo2 + 2Fc2)/3
5647 reflections	(Δ/σ)max = 0.013
281 parameters	Δρmax = 1.34 e Å−3
12 restraints	Δρmin = −1.07 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	Occ. (<1)
Br1	1.011728 (9)	0.62404 (4)	0.390312 (15)	0.03786 (10)
Cl1	0.57351 (2)	0.43637 (7)	0.01505 (3)	0.02585 (13)
O1	0.77362 (6)	0.54096 (17)	0.10987 (8)	0.0178 (3)
N6	0.77924 (7)	0.65177 (19)	0.21947 (9)	0.0146 (3)
N1	0.65391 (7)	0.62551 (19)	−0.00380 (9)	0.0140 (3)
O2	0.75496 (6)	0.77690 (18)	0.30583 (8)	0.0201 (3)
N5	0.69524 (7)	0.6804 (2)	0.19766 (10)	0.0167 (4)
N4	0.65662 (7)	0.8290 (2)	0.05861 (10)	0.0178 (4)
C8	0.93903 (9)	0.6319 (3)	0.33660 (13)	0.0239 (5)
C7	0.90634 (9)	0.5992 (3)	0.37241 (12)	0.0222 (5)
H7	0.9201	0.5716	0.4229	0.027*
C6	0.85319 (9)	0.6071 (2)	0.33357 (12)	0.0188 (4)
H6	0.8301	0.5844	0.3572	0.023*
C5	0.83404 (8)	0.6485 (2)	0.25987 (11)	0.0151 (4)
C4	0.75450 (8)	0.5905 (2)	0.15058 (11)	0.0142 (4)
C2	0.69640 (8)	0.6013 (2)	0.13411 (11)	0.0146 (4)
H2	0.6813	0.4981	0.1311	0.018*
C1	0.66895 (8)	0.6853 (2)	0.06412 (11)	0.0137 (4)
C15	0.65419 (8)	0.4734 (2)	−0.02730 (11)	0.0143 (4)
C16	0.61720 (8)	0.3741 (2)	−0.02185 (11)	0.0160 (4)
C17	0.61567 (9)	0.2265 (2)	−0.04531 (12)	0.0207 (4)
H17	0.5907	0.1579	−0.0414	0.025*
C18	0.65116 (9)	0.1805 (3)	−0.07466 (12)	0.0213 (4)
H18	0.6503	0.0795	−0.0912	0.026*
C10	0.86722 (9)	0.6800 (3)	0.22433 (12)	0.0201 (4)
H10	0.8537	0.7077	0.1738	0.024*
C9	0.92031 (9)	0.6708 (3)	0.26306 (13)	0.0239 (5)
H9	0.9435	0.6911	0.2393	0.029*
C3	0.74322 (8)	0.7112 (2)	0.24774 (12)	0.0160 (4)
N2	0.63105 (7)	0.7362 (2)	−0.05322 (10)	0.0176 (4)
N3	0.63295 (7)	0.8568 (2)	−0.01536 (11)	0.0197 (4)
C19	0.68770 (8)	0.2792 (2)	−0.08031 (11)	0.0178 (4)
H19	0.7118	0.2447	−0.1003	0.021*
C20	0.68992 (7)	0.4282 (2)	−0.05726 (10)	0.0122 (3)
C11	0.64797 (8)	0.7115 (3)	0.21019 (12)	0.0190 (4)
H11A	0.6218	0.7550	0.1649	0.023*
H11B	0.6555	0.7871	0.2500	0.023*
C12	0.62577 (9)	0.5705 (3)	0.23131 (13)	0.0228 (5)
H12A	0.6514	0.5293	0.2778	0.027*
H12B	0.6196	0.4931	0.1925	0.027*
C13	0.57507 (10)	0.6024 (3)	0.24118 (14)	0.0316 (6)
H13A	0.5685	0.5205	0.2707	0.038*	0.67 (3)
H13B	0.5784	0.6979	0.2687	0.038*	0.67 (3)
H13C	0.5822	0.6736	0.2827	0.038*	0.33 (3)
H13D	0.5625	0.5072	0.2548	0.038*	0.33 (3)
C14A	0.5291 (4)	0.614 (2)	0.1675 (7)	0.046 (2)	0.67 (3)
H14A	0.5353	0.6959	0.1383	0.069*	0.67 (3)
H14B	0.4975	0.6356	0.1763	0.069*	0.67 (3)
H14C	0.5250	0.5188	0.1407	0.069*	0.67 (3)
C14B	0.5321 (10)	0.668 (3)	0.1735 (16)	0.046 (2)	0.33 (3)
H14D	0.5426	0.7676	0.1626	0.069*	0.33 (3)
H14E	0.5003	0.6774	0.1831	0.069*	0.33 (3)
H14F	0.5258	0.6009	0.1313	0.069*	0.33 (3)
C21	0.73027 (7)	0.5400 (2)	−0.06540 (10)	0.0122 (3)
H21A	0.7124	0.6299	−0.0922	0.018*
H21B	0.7489	0.4912	−0.0927	0.018*
H21C	0.7549	0.5695	−0.0165	0.018*

	U11	U22	U33	U12	U13	U23
Br1	0.01517 (12)	0.0592 (2)	0.03350 (15)	0.00097 (11)	0.00299 (10)	−0.00200 (13)
Cl1	0.0240 (3)	0.0277 (3)	0.0311 (3)	−0.0026 (2)	0.0164 (2)	−0.0040 (2)
O1	0.0192 (7)	0.0203 (7)	0.0158 (7)	0.0027 (6)	0.0089 (6)	−0.0023 (6)
N6	0.0153 (8)	0.0169 (8)	0.0131 (8)	0.0000 (7)	0.0071 (7)	−0.0021 (7)
N1	0.0143 (8)	0.0136 (8)	0.0140 (8)	0.0004 (6)	0.0052 (7)	0.0007 (7)
O2	0.0221 (8)	0.0236 (8)	0.0166 (7)	−0.0013 (6)	0.0096 (6)	−0.0064 (6)
N5	0.0166 (8)	0.0209 (9)	0.0144 (8)	0.0002 (7)	0.0080 (7)	−0.0034 (7)
N4	0.0196 (9)	0.0148 (8)	0.0204 (9)	−0.0006 (7)	0.0093 (7)	0.0001 (7)
C8	0.0136 (10)	0.0303 (12)	0.0247 (11)	−0.0003 (9)	0.0038 (9)	−0.0032 (10)
C7	0.0200 (10)	0.0287 (12)	0.0149 (10)	0.0007 (9)	0.0032 (8)	−0.0003 (9)
C6	0.0205 (10)	0.0210 (10)	0.0164 (10)	−0.0014 (8)	0.0089 (8)	−0.0004 (8)
C5	0.0142 (9)	0.0156 (9)	0.0154 (10)	−0.0002 (7)	0.0054 (8)	−0.0016 (8)
C4	0.0162 (9)	0.0119 (9)	0.0142 (9)	0.0017 (7)	0.0057 (8)	0.0016 (7)
C2	0.0156 (9)	0.0156 (9)	0.0139 (9)	0.0000 (7)	0.0071 (8)	−0.0012 (8)
C1	0.0128 (9)	0.0137 (9)	0.0166 (10)	−0.0007 (7)	0.0076 (8)	−0.0005 (8)
C15	0.0166 (9)	0.0131 (9)	0.0124 (9)	0.0015 (7)	0.0047 (8)	0.0003 (7)
C16	0.0158 (9)	0.0188 (10)	0.0150 (9)	0.0003 (8)	0.0076 (8)	0.0000 (8)
C17	0.0265 (11)	0.0166 (10)	0.0224 (11)	−0.0049 (9)	0.0133 (9)	−0.0014 (9)
C18	0.0305 (12)	0.0156 (10)	0.0202 (11)	0.0005 (9)	0.0123 (9)	−0.0004 (8)
C10	0.0202 (10)	0.0230 (11)	0.0178 (10)	0.0000 (9)	0.0082 (9)	0.0004 (9)
C9	0.0185 (11)	0.0313 (12)	0.0251 (12)	−0.0021 (9)	0.0121 (9)	−0.0012 (10)
C3	0.0178 (10)	0.0167 (10)	0.0165 (10)	0.0004 (8)	0.0098 (8)	0.0016 (8)
N2	0.0184 (8)	0.0164 (8)	0.0177 (9)	0.0026 (7)	0.0065 (7)	0.0042 (7)
N3	0.0209 (9)	0.0168 (9)	0.0225 (9)	0.0010 (7)	0.0096 (8)	0.0029 (7)
C19	0.0223 (10)	0.0190 (10)	0.0151 (10)	0.0031 (8)	0.0105 (8)	0.0007 (8)
C20	0.0127 (6)	0.0166 (7)	0.0085 (6)	0.0002 (5)	0.0054 (5)	0.0007 (5)
C11	0.0166 (10)	0.0238 (11)	0.0197 (10)	0.0024 (8)	0.0104 (8)	0.0002 (9)
C12	0.0230 (11)	0.0280 (12)	0.0209 (11)	−0.0025 (9)	0.0123 (9)	−0.0014 (9)
C13	0.0252 (12)	0.0470 (16)	0.0291 (13)	−0.0084 (11)	0.0176 (11)	−0.0046 (12)
C14A	0.0167 (19)	0.079 (8)	0.043 (3)	−0.011 (4)	0.0123 (19)	−0.004 (5)
C14B	0.0167 (19)	0.079 (8)	0.043 (3)	−0.011 (4)	0.0123 (19)	−0.004 (5)
C21	0.0127 (6)	0.0166 (7)	0.0085 (6)	0.0002 (5)	0.0054 (5)	0.0007 (5)

Br1—C8	1.899 (2)	C18—H18	0.9500
Cl1—C16	1.732 (2)	C18—C19	1.381 (3)
O1—C4	1.203 (2)	C10—H10	0.9500
N6—C5	1.430 (3)	C10—C9	1.387 (3)
N6—C4	1.375 (3)	C9—H9	0.9500
N6—C3	1.424 (3)	N2—N3	1.292 (3)
N1—C1	1.346 (3)	C19—H19	0.9500
N1—C15	1.427 (3)	C19—C20	1.390 (3)
N1—N2	1.356 (2)	C20—C21	1.555 (3)
O2—C3	1.210 (3)	C11—H11A	0.9900
N5—C2	1.444 (3)	C11—H11B	0.9900
N5—C3	1.353 (3)	C11—C12	1.522 (3)
N5—C11	1.459 (3)	C12—H12A	0.9900
N4—C1	1.314 (3)	C12—H12B	0.9900
N4—N3	1.370 (3)	C12—C13	1.528 (3)
C8—C7	1.380 (3)	C13—H13A	0.9900
C8—C9	1.380 (3)	C13—H13B	0.9900
C7—H7	0.9500	C13—H13C	0.9900
C7—C6	1.388 (3)	C13—H13D	0.9900
C6—H6	0.9500	C13—C14A	1.527 (12)
C6—C5	1.388 (3)	C13—C14B	1.53 (3)
C5—C10	1.386 (3)	C14A—H14A	0.9800
C4—C2	1.532 (3)	C14A—H14B	0.9800
C2—H2	1.0000	C14A—H14C	0.9800
C2—C1	1.493 (3)	C14B—H14D	0.9800
C15—C16	1.393 (3)	C14B—H14E	0.9800
C15—C20	1.398 (3)	C14B—H14F	0.9800
C16—C17	1.383 (3)	C21—H21A	0.9800
C17—H17	0.9500	C21—H21B	0.9800
C17—C18	1.386 (3)	C21—H21C	0.9800
C4—N6—C5	124.55 (17)	C10—C9—H9	120.4
C4—N6—C3	111.50 (17)	O2—C3—N6	124.71 (19)
C3—N6—C5	123.86 (17)	O2—C3—N5	128.24 (19)
C1—N1—C15	130.94 (17)	N5—C3—N6	107.04 (17)
C1—N1—N2	107.96 (16)	N3—N2—N1	106.38 (16)
N2—N1—C15	120.77 (16)	N2—N3—N4	111.07 (17)
C2—N5—C11	123.99 (17)	C18—C19—H19	119.4
C3—N5—C2	112.53 (17)	C18—C19—C20	121.21 (19)
C3—N5—C11	123.23 (17)	C20—C19—H19	119.4
C1—N4—N3	105.46 (17)	C15—C20—C21	121.55 (18)
C7—C8—Br1	118.98 (18)	C19—C20—C15	117.37 (18)
C9—C8—Br1	119.19 (17)	C19—C20—C21	121.08 (17)
C9—C8—C7	121.8 (2)	N5—C11—H11A	109.1
C8—C7—H7	120.4	N5—C11—H11B	109.1
C8—C7—C6	119.1 (2)	N5—C11—C12	112.39 (18)
C6—C7—H7	120.4	H11A—C11—H11B	107.9
C7—C6—H6	120.3	C12—C11—H11A	109.1
C5—C6—C7	119.4 (2)	C12—C11—H11B	109.1
C5—C6—H6	120.3	C11—C12—H12A	109.2
C6—C5—N6	119.21 (18)	C11—C12—H12B	109.2
C6—C5—C10	121.0 (2)	C11—C12—C13	112.1 (2)
C10—C5—N6	119.76 (19)	H12A—C12—H12B	107.9
O1—C4—N6	128.02 (19)	C13—C12—H12A	109.2
O1—C4—C2	125.92 (19)	C13—C12—H12B	109.2
N6—C4—C2	106.04 (16)	C12—C13—H13A	109.2
N5—C2—C4	102.73 (16)	C12—C13—H13B	109.2
N5—C2—H2	110.2	C12—C13—H13C	108.6
N5—C2—C1	112.39 (17)	C12—C13—H13D	108.6
C4—C2—H2	110.2	C12—C13—C14B	114.7 (10)
C1—C2—C4	110.81 (16)	H13A—C13—H13B	107.9
C1—C2—H2	110.2	H13C—C13—H13D	107.6
N1—C1—C2	124.98 (18)	C14A—C13—C12	112.1 (5)
N4—C1—N1	109.13 (18)	C14A—C13—H13A	109.2
N4—C1—C2	125.88 (19)	C14A—C13—H13B	109.2
C16—C15—N1	118.47 (18)	C14B—C13—H13C	108.6
C16—C15—C20	121.44 (19)	C14B—C13—H13D	108.6
C20—C15—N1	120.05 (18)	C13—C14A—H14A	109.5
C15—C16—Cl1	119.55 (16)	C13—C14A—H14B	109.5
C17—C16—Cl1	120.31 (16)	C13—C14A—H14C	109.5
C17—C16—C15	120.14 (19)	C13—C14B—H14D	109.5
C16—C17—H17	120.6	C13—C14B—H14E	109.5
C18—C17—C16	118.8 (2)	C13—C14B—H14F	109.5
C18—C17—H17	120.6	H14D—C14B—H14E	109.5
C17—C18—H18	119.5	H14D—C14B—H14F	109.5
C19—C18—C17	121.1 (2)	H14E—C14B—H14F	109.5
C19—C18—H18	119.5	C20—C21—H21A	109.5
C5—C10—H10	120.2	C20—C21—H21B	109.5
C5—C10—C9	119.5 (2)	C20—C21—H21C	109.5
C9—C10—H10	120.2	H21A—C21—H21B	109.5
C8—C9—C10	119.1 (2)	H21A—C21—H21C	109.5
C8—C9—H9	120.4	H21B—C21—H21C	109.5
Br1—C8—C7—C6	179.01 (17)	C1—N1—C15—C20	−107.9 (2)
Br1—C8—C9—C10	−178.49 (18)	C1—N1—N2—N3	0.3 (2)
Cl1—C16—C17—C18	179.91 (17)	C1—N4—N3—N2	−0.2 (2)
O1—C4—C2—N5	−175.0 (2)	C15—N1—C1—N4	−173.71 (19)
O1—C4—C2—C1	−54.7 (3)	C15—N1—C1—C2	7.6 (3)
N6—C5—C10—C9	−177.4 (2)	C15—N1—N2—N3	174.40 (18)
N6—C4—C2—N5	3.6 (2)	C15—C16—C17—C18	−0.5 (3)
N6—C4—C2—C1	123.80 (18)	C16—C15—C20—C19	−1.1 (3)
N1—C15—C16—Cl1	−1.6 (3)	C16—C15—C20—C21	178.28 (18)
N1—C15—C16—C17	178.84 (19)	C16—C17—C18—C19	0.3 (3)
N1—C15—C20—C19	−178.92 (18)	C17—C18—C19—C20	−0.4 (3)
N1—C15—C20—C21	0.4 (3)	C18—C19—C20—C15	0.8 (3)
N1—N2—N3—N4	−0.1 (2)	C18—C19—C20—C21	−178.54 (19)
N5—C2—C1—N1	−164.34 (18)	C9—C8—C7—C6	−0.7 (4)
N5—C2—C1—N4	17.2 (3)	C3—N6—C5—C6	42.6 (3)
N5—C11—C12—C13	−177.58 (19)	C3—N6—C5—C10	−140.3 (2)
C8—C7—C6—C5	−0.4 (3)	C3—N6—C4—O1	174.4 (2)
C7—C8—C9—C10	1.2 (4)	C3—N6—C4—C2	−4.1 (2)
C7—C6—C5—N6	177.97 (19)	C3—N5—C2—C4	−1.9 (2)
C7—C6—C5—C10	0.9 (3)	C3—N5—C2—C1	−121.07 (19)
C6—C5—C10—C9	−0.4 (3)	C3—N5—C11—C12	−101.3 (2)
C5—N6—C4—O1	−9.1 (3)	N2—N1—C1—N4	−0.5 (2)
C5—N6—C4—C2	172.39 (18)	N2—N1—C1—C2	−179.10 (18)
C5—N6—C3—O2	6.8 (3)	N2—N1—C15—C16	−98.3 (2)
C5—N6—C3—N5	−173.55 (18)	N2—N1—C15—C20	79.6 (2)
C5—C10—C9—C8	−0.7 (4)	N3—N4—C1—N1	0.4 (2)
C4—N6—C5—C6	−133.4 (2)	N3—N4—C1—C2	179.02 (18)
C4—N6—C5—C10	43.7 (3)	C20—C15—C16—Cl1	−179.49 (16)
C4—N6—C3—O2	−176.7 (2)	C20—C15—C16—C17	1.0 (3)
C4—N6—C3—N5	2.9 (2)	C11—N5—C2—C4	−176.40 (18)
C4—C2—C1—N1	81.4 (2)	C11—N5—C2—C1	64.5 (3)
C4—C2—C1—N4	−97.0 (2)	C11—N5—C3—N6	174.12 (18)
C2—N5—C3—N6	−0.4 (2)	C11—N5—C3—O2	−6.3 (4)
C2—N5—C3—O2	179.2 (2)	C11—C12—C13—C14A	78.3 (8)
C2—N5—C11—C12	72.6 (3)	C11—C12—C13—C14B	58.3 (12)
C1—N1—C15—C16	74.2 (3)