(Z)-Methyl 4-({3-[(2,5-dioxoimidazolidin-4-yl-idene)meth-yl]-1H-indol-1-yl}meth-yl)benzoate.

In the title compound, C(21)H(17)N(3)O(4), pairs of mol-ecules form a planar[maximum deviation 0.0566 (9) Å] centrosymmetric imidazole dimer via two N-H⋯O hydrogen bonds. These dimeric units are linked by further N-H⋯O hydrogen bonds between the ester carbonyl group and the imidazolidine ring, formiing chains parallel to the c-axis direction. In addition, there are π-π stacking inter-actions between the planar imidazole pairs, with an inter-planar spacing of 3.301 (2) Å. There is a double bond with Z geometry connecting the imidazolidine and indole units.

Related literature

For general background to the radiosensitization activity of (Z)-2-(N-benzyl­indol-3-ylmethyl­ene)quinuclidin-3-one and (Z)-(±)-2-(N-benzyl­indol-3-ylmethyl­ene)quinuclidin-3-ol derivatives, see: Sekhar et al. (2003 ▶); Sonar et al., (2007 ▶). For related structures, see: Mason et al. (2003 ▶); Zarza et al. (1988 ▶).

Experimental

Crystal data

C21H17N3O4

M = 375.38

Triclinic,

a = 7.6390 (1) Å

b = 8.0013 (1) Å

c = 15.0405 (3) Å

α = 91.9853 (9)°

β = 96.2291 (9)°

γ = 104.4242 (9)°

V = 883.25 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 90.0 (2) K

0.25 × 0.22 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.976, T max = 0.985

19513 measured reflections

3997 independent reflections

3595 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.07

3997 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041020/fj2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041020/fj2166Isup2.hkl

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

C21H17N3O4	Z = 2
Mr = 375.38	F(000) = 392
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6390 (1) Å	Cell parameters from 3966 reflections
b = 8.0013 (1) Å	θ = 1.0–27.5°
c = 15.0405 (3) Å	µ = 0.10 mm−1
α = 91.9853 (9)°	T = 90 K
β = 96.2291 (9)°	Block, colourless
γ = 104.4242 (9)°	0.25 × 0.22 × 0.15 mm
V = 883.25 (2) Å3

Nonius KappaCCD diffractometer	3997 independent reflections
Radiation source: fine-focus sealed tube	3595 reflections with I > 2σ(I)
graphite	Rint = 0.015
Detector resolution: 18 pixels mm-1	θmax = 27.4°, θmin = 1.4°
ω scans at fixed χ = 55°	h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −10→10
Tmin = 0.976, Tmax = 0.985	l = −19→19
19513 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.3949P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3997 reflections	Δρmax = 0.48 e Å−3
255 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.090 (15)

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 > 2σ(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
N1	0.62738 (14)	0.06683 (14)	0.69424 (7)	0.0179 (2)
C1	0.64933 (17)	0.16626 (17)	0.62219 (8)	0.0189 (3)
H1	0.7632	0.2298	0.6066	0.023*
C2	0.44342 (17)	−0.00489 (16)	0.69679 (8)	0.0173 (3)
C3	0.35580 (18)	−0.11990 (17)	0.75529 (9)	0.0196 (3)
H3	0.4221	−0.1562	0.8048	0.024*
C4	0.16793 (19)	−0.17896 (17)	0.73816 (9)	0.0221 (3)
H4	0.1044	−0.2593	0.7760	0.027*
C5	0.06985 (18)	−0.12239 (18)	0.66605 (9)	0.0226 (3)
H5	−0.0589	−0.1643	0.6562	0.027*
C6	0.15795 (18)	−0.00650 (18)	0.60918 (9)	0.0209 (3)
H6	0.0904	0.0331	0.5613	0.025*
C7	0.34801 (17)	0.05157 (16)	0.62314 (8)	0.0177 (3)
C8	0.48188 (17)	0.16104 (17)	0.57534 (8)	0.0181 (3)
C9	0.44195 (17)	0.23455 (16)	0.49230 (8)	0.0187 (3)
H9	0.3177	0.2033	0.4673	0.022*
C10	0.55628 (18)	0.34163 (16)	0.44489 (8)	0.0186 (3)
N11	0.74423 (15)	0.41748 (15)	0.46348 (7)	0.0197 (3)
H11	0.8114	0.4057	0.5131	0.024*
O12	0.96568 (13)	0.59079 (14)	0.38998 (7)	0.0276 (3)
C12	0.80892 (18)	0.51160 (16)	0.39495 (9)	0.0198 (3)
N13	0.66123 (15)	0.50316 (14)	0.33104 (7)	0.0205 (3)
H13	0.6677	0.5574	0.2811	0.025*
O14	0.35435 (13)	0.36140 (13)	0.31095 (7)	0.0247 (2)
C14	0.50269 (18)	0.39906 (16)	0.35539 (8)	0.0191 (3)
C15	0.77114 (17)	0.06679 (17)	0.76616 (8)	0.0197 (3)
H15A	0.8908	0.1013	0.7432	0.024*
H15B	0.7557	−0.0516	0.7868	0.024*
C16	0.76755 (17)	0.19009 (17)	0.84440 (8)	0.0186 (3)
C17	0.77627 (19)	0.36332 (18)	0.83052 (9)	0.0230 (3)
H17	0.7891	0.4045	0.7725	0.028*
C18	0.76628 (19)	0.47605 (17)	0.90102 (9)	0.0226 (3)
H18	0.7718	0.5937	0.8910	0.027*
C19	0.74814 (17)	0.41658 (17)	0.98642 (8)	0.0190 (3)
C20	0.7411 (2)	0.24417 (18)	1.00064 (9)	0.0244 (3)
H20	0.7298	0.2033	1.0588	0.029*
C21	0.7508 (2)	0.13161 (18)	0.92977 (9)	0.0242 (3)
H21	0.7459	0.0140	0.9398	0.029*
O22	0.70603 (16)	0.48178 (14)	1.13762 (7)	0.0298 (3)
C22	0.73352 (17)	0.53113 (17)	1.06416 (9)	0.0196 (3)
O23	0.75282 (15)	0.69475 (13)	1.04391 (6)	0.0274 (3)
C23	0.7376 (2)	0.8120 (2)	1.11646 (10)	0.0316 (4)
H23A	0.6119	0.7839	1.1309	0.047*
H23B	0.7709	0.9311	1.0982	0.047*
H23C	0.8197	0.8005	1.1694	0.047*

	U11	U22	U33	U12	U13	U23
N1	0.0158 (5)	0.0211 (5)	0.0150 (5)	0.0023 (4)	0.0008 (4)	−0.0007 (4)
C1	0.0186 (6)	0.0219 (6)	0.0150 (6)	0.0023 (5)	0.0034 (4)	−0.0005 (5)
C2	0.0163 (6)	0.0184 (6)	0.0162 (6)	0.0033 (5)	0.0020 (4)	−0.0038 (5)
C3	0.0216 (6)	0.0186 (6)	0.0180 (6)	0.0039 (5)	0.0034 (5)	−0.0005 (5)
C4	0.0230 (7)	0.0205 (6)	0.0219 (6)	0.0018 (5)	0.0077 (5)	−0.0007 (5)
C5	0.0168 (6)	0.0256 (7)	0.0236 (7)	0.0016 (5)	0.0044 (5)	−0.0046 (5)
C6	0.0196 (6)	0.0248 (7)	0.0173 (6)	0.0052 (5)	0.0003 (5)	−0.0022 (5)
C7	0.0189 (6)	0.0196 (6)	0.0141 (6)	0.0040 (5)	0.0029 (4)	−0.0025 (4)
C8	0.0185 (6)	0.0198 (6)	0.0152 (6)	0.0031 (5)	0.0034 (4)	−0.0011 (4)
C9	0.0194 (6)	0.0184 (6)	0.0176 (6)	0.0040 (5)	0.0025 (5)	−0.0010 (5)
C10	0.0202 (6)	0.0176 (6)	0.0176 (6)	0.0047 (5)	0.0018 (5)	−0.0010 (5)
N11	0.0199 (5)	0.0237 (6)	0.0156 (5)	0.0054 (4)	0.0020 (4)	0.0028 (4)
O12	0.0211 (5)	0.0310 (6)	0.0260 (5)	−0.0024 (4)	0.0022 (4)	0.0074 (4)
C12	0.0234 (6)	0.0173 (6)	0.0177 (6)	0.0032 (5)	0.0021 (5)	0.0006 (5)
N13	0.0232 (6)	0.0196 (5)	0.0172 (5)	0.0025 (4)	0.0013 (4)	0.0039 (4)
O14	0.0234 (5)	0.0281 (5)	0.0219 (5)	0.0058 (4)	−0.0005 (4)	0.0062 (4)
C14	0.0222 (6)	0.0180 (6)	0.0181 (6)	0.0066 (5)	0.0036 (5)	0.0011 (5)
C15	0.0170 (6)	0.0242 (6)	0.0174 (6)	0.0056 (5)	−0.0011 (5)	−0.0013 (5)
C16	0.0151 (6)	0.0222 (6)	0.0174 (6)	0.0041 (5)	−0.0008 (4)	−0.0009 (5)
C17	0.0283 (7)	0.0230 (7)	0.0158 (6)	0.0032 (5)	0.0021 (5)	0.0024 (5)
C18	0.0300 (7)	0.0185 (6)	0.0180 (6)	0.0037 (5)	0.0018 (5)	0.0021 (5)
C19	0.0187 (6)	0.0206 (6)	0.0166 (6)	0.0038 (5)	0.0000 (5)	−0.0001 (5)
C20	0.0336 (8)	0.0239 (7)	0.0167 (6)	0.0089 (6)	0.0033 (5)	0.0037 (5)
C21	0.0330 (7)	0.0202 (6)	0.0205 (6)	0.0091 (5)	0.0023 (5)	0.0024 (5)
O22	0.0460 (7)	0.0272 (5)	0.0174 (5)	0.0101 (5)	0.0075 (4)	0.0024 (4)
C22	0.0182 (6)	0.0214 (6)	0.0180 (6)	0.0039 (5)	−0.0010 (5)	0.0012 (5)
O23	0.0444 (6)	0.0197 (5)	0.0185 (5)	0.0090 (4)	0.0046 (4)	−0.0005 (4)
C23	0.0490 (10)	0.0245 (7)	0.0224 (7)	0.0130 (7)	0.0023 (6)	−0.0047 (6)

N1—C1	1.3668 (17)	C12—N13	1.3869 (17)
N1—C2	1.3846 (16)	N13—C14	1.3819 (17)
N1—C15	1.4554 (16)	N13—H13	0.8800
C1—C8	1.3821 (18)	O14—C14	1.2137 (16)
C1—H1	0.9500	C15—C16	1.5162 (17)
C2—C3	1.3951 (18)	C15—H15A	0.9900
C2—C7	1.4093 (18)	C15—H15B	0.9900
C3—C4	1.3866 (19)	C16—C21	1.3898 (18)
C3—H3	0.9500	C16—C17	1.3951 (19)
C4—C5	1.403 (2)	C17—C18	1.3890 (19)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.3833 (19)	C18—C19	1.3940 (18)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.3996 (18)	C19—C20	1.3921 (19)
C6—H6	0.9500	C19—C22	1.4916 (18)
C7—C8	1.4445 (17)	C20—C21	1.3915 (19)
C8—C9	1.4340 (18)	C20—H20	0.9500
C9—C10	1.3454 (18)	C21—H21	0.9500
C9—H9	0.9500	O22—C22	1.2083 (16)
C10—N11	1.4053 (17)	C22—O23	1.3303 (16)
C10—C14	1.4858 (18)	O23—C23	1.4475 (16)
N11—C12	1.3612 (17)	C23—H23A	0.9800
N11—H11	0.8800	C23—H23B	0.9800
O12—C12	1.2189 (17)	C23—H23C	0.9800
C1—N1—C2	109.12 (11)	C14—N13—H13	124.2
C1—N1—C15	124.49 (11)	C12—N13—H13	124.2
C2—N1—C15	125.24 (11)	O14—C14—N13	126.35 (12)
N1—C1—C8	110.17 (11)	O14—C14—C10	128.62 (12)
N1—C1—H1	124.9	N13—C14—C10	105.00 (11)
C8—C1—H1	124.9	N1—C15—C16	111.22 (10)
N1—C2—C3	129.95 (12)	N1—C15—H15A	109.4
N1—C2—C7	107.54 (11)	C16—C15—H15A	109.4
C3—C2—C7	122.43 (12)	N1—C15—H15B	109.4
C4—C3—C2	117.24 (12)	C16—C15—H15B	109.4
C4—C3—H3	121.4	H15A—C15—H15B	108.0
C2—C3—H3	121.4	C21—C16—C17	119.35 (12)
C3—C4—C5	121.30 (12)	C21—C16—C15	120.72 (12)
C3—C4—H4	119.3	C17—C16—C15	119.91 (11)
C5—C4—H4	119.3	C18—C17—C16	120.43 (12)
C6—C5—C4	120.95 (12)	C18—C17—H17	119.8
C6—C5—H5	119.5	C16—C17—H17	119.8
C4—C5—H5	119.5	C17—C18—C19	120.04 (12)
C5—C6—C7	119.10 (12)	C17—C18—H18	120.0
C5—C6—H6	120.5	C19—C18—H18	120.0
C7—C6—H6	120.5	C20—C19—C18	119.66 (12)
C6—C7—C2	118.93 (12)	C20—C19—C22	118.03 (12)
C6—C7—C8	133.86 (12)	C18—C19—C22	122.31 (12)
C2—C7—C8	107.19 (11)	C21—C20—C19	120.11 (12)
C1—C8—C9	128.94 (12)	C21—C20—H20	119.9
C1—C8—C7	105.98 (11)	C19—C20—H20	119.9
C9—C8—C7	124.90 (12)	C16—C21—C20	120.42 (13)
C10—C9—C8	128.91 (12)	C16—C21—H21	119.8
C10—C9—H9	115.5	C20—C21—H21	119.8
C8—C9—H9	115.5	O22—C22—O23	123.20 (12)
C9—C10—N11	130.48 (12)	O22—C22—C19	124.14 (12)
C9—C10—C14	124.45 (12)	O23—C22—C19	112.66 (11)
N11—C10—C14	105.04 (11)	C22—O23—C23	115.26 (11)
C12—N11—C10	111.28 (11)	O23—C23—H23A	109.5
C12—N11—H11	124.4	O23—C23—H23B	109.5
C10—N11—H11	124.4	H23A—C23—H23B	109.5
O12—C12—N11	127.32 (12)	O23—C23—H23C	109.5
O12—C12—N13	125.72 (12)	H23A—C23—H23C	109.5
N11—C12—N13	106.95 (11)	H23B—C23—H23C	109.5
C14—N13—C12	111.67 (11)
C2—N1—C1—C8	−0.64 (14)	C10—N11—C12—N13	1.94 (14)
C15—N1—C1—C8	−168.87 (11)	O12—C12—N13—C14	178.35 (13)
C1—N1—C2—C3	177.11 (13)	N11—C12—N13—C14	−2.48 (15)
C15—N1—C2—C3	−14.8 (2)	C12—N13—C14—O14	−176.40 (13)
C1—N1—C2—C7	0.36 (14)	C12—N13—C14—C10	1.99 (14)
C15—N1—C2—C7	168.48 (11)	C9—C10—C14—O14	−0.3 (2)
N1—C2—C3—C4	−176.00 (12)	N11—C10—C14—O14	177.59 (13)
C7—C2—C3—C4	0.32 (18)	C9—C10—C14—N13	−178.67 (12)
C2—C3—C4—C5	−1.33 (19)	N11—C10—C14—N13	−0.75 (13)
C3—C4—C5—C6	0.5 (2)	C1—N1—C15—C16	94.54 (14)
C4—C5—C6—C7	1.38 (19)	C2—N1—C15—C16	−71.81 (15)
C5—C6—C7—C2	−2.33 (18)	N1—C15—C16—C21	122.96 (13)
C5—C6—C7—C8	175.72 (13)	N1—C15—C16—C17	−55.33 (16)
N1—C2—C7—C6	178.56 (11)	C21—C16—C17—C18	−0.7 (2)
C3—C2—C7—C6	1.52 (18)	C15—C16—C17—C18	177.60 (12)
N1—C2—C7—C8	0.03 (14)	C16—C17—C18—C19	0.3 (2)
C3—C2—C7—C8	−177.01 (11)	C17—C18—C19—C20	0.4 (2)
N1—C1—C8—C9	−174.63 (12)	C17—C18—C19—C22	−178.91 (12)
N1—C1—C8—C7	0.63 (14)	C18—C19—C20—C21	−0.5 (2)
C6—C7—C8—C1	−178.62 (14)	C22—C19—C20—C21	178.79 (12)
C2—C7—C8—C1	−0.40 (14)	C17—C16—C21—C20	0.6 (2)
C6—C7—C8—C9	−3.1 (2)	C15—C16—C21—C20	−177.73 (12)
C2—C7—C8—C9	175.11 (12)	C19—C20—C21—C16	0.0 (2)
C1—C8—C9—C10	−7.9 (2)	C20—C19—C22—O22	−4.2 (2)
C7—C8—C9—C10	177.63 (13)	C18—C19—C22—O22	175.06 (13)
C8—C9—C10—N11	−2.6 (2)	C20—C19—C22—O23	176.23 (12)
C8—C9—C10—C14	174.74 (12)	C18—C19—C22—O23	−4.50 (18)
C9—C10—N11—C12	177.01 (13)	O22—C22—O23—C23	−0.3 (2)
C14—C10—N11—C12	−0.74 (14)	C19—C22—O23—C23	179.24 (11)
C10—N11—C12—O12	−178.91 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12i	0.88	2.11	2.9658 (15)	163
N13—H13···O22ii	0.88	2.29	2.9699 (15)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O12i	0.88	2.11	2.9658 (15)	163
N13—H13⋯O22ii	0.88	2.29	2.9699 (15)	134

Symmetry codes: (i) ; (ii) .