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

Penthala, N.R.; Reddy, T.R.Y.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536808041020

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o62-o63

doi:10.1107/S1600536808041020

Open

access

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

Narsimha Reddy Penthala,^a Thirupathi Reddy Yerram Reddy,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pcrooks@uky.edu

(Received 21 October 2008; accepted 4 December 2008; online 10 December 2008)

In the title compound, C₂₁H₁₇N₃O₄, pairs of molecules 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 interactions between the planar imidazole pairs, with an interplanar 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_r = 375.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.07
3997 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) x, y, z-1.

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.

Supporting information

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

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

checkCIF report

Comment top

In continuation of our work on the radiosensitization activity of (Z)-2-(N-benzylindol-3-ylmethylene)quinuclidin-3-one and (Z)-(±)-2-(N-benzylindol-3-ylmethylene) quinuclidin-3-ol derivatives (Sekhar et al., 2003; Sonar et al., 2007), we have undertaken the design, synthesis and structural analysis of a series of (N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione analogs with different substituents on both indole moiety and on the benzene ring of the N-benzyl group. The primary goal for X-ray analysis of the title compound is to confirm the double-bond geometry and to obtain detailed information on the structural conformation of the molecule. This information will be useful in structure-activity relationship (SAR) analysis. The title compound was prepared by the reaction of methyl 4-((3-formyl-1H-indol-1-yl)methyl)benzoate with imidazolidine-2,4-dione in the presence of ammonium acetate in acetic acid at 391 K. The compound was crystallized from a mixture of methanol and ethylacetate. The molecular structure and the atom-numbering scheme are shown in Fig.1. The indole ring is planar with bond distances and angles comparable with those previously reported for other indole derivatives (Mason et al., 2003; Zarza, et al., 1988). The X-ray studies revealed that the title compound is the Z isomer. The C8—C9 bond is in a transoid geometry with respect to the C10—C14 bond. The olefinic bond (C9=C10) has a planar atomic arrangement, since the r.m.s. deviation from the mean plane passing through atoms C1, C8, C9, N11 is 0.0349 (6) Å. Deviations from ideal geometry are observed in the bond angles around atoms C9, C10 and N11 (130.48 (12)°) due to repulsion between the indole ring C1 hydrogen and imidazolidine ring N11 hydrogen. The imidazolidine ring, which makes a dihedral angle of 10.03 (7)° with the adjacent aromatic ring, presents very small distortions around atoms N11, C12, N13 and C14.

Significant intermolecular hydrogen-bonding interactions are found between N(11)—H(11)···O(12) and N(13)—H(13)···O(22), and molecules are linked into chains by N—H···O hydrogen bonding.

Related literature top

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 top

A mixture of methyl 4-((3-formyl-1H-indol-1-yl)methyl)benzoate (0.5 g, 1.70 mmol), imidazolidine-2,4-dione (0.18 g, 1.80 mmol) and ammonium acetate (0.132 g, 1.71 mmol) was stirred in acetic acid (5 ml) at 391 K for 8 hrs. The reaction mixture was cooled to room temperature and the yellow solid that separated was collected by filtration, washed with cold water and dried to afford the crude product. Crystallization from methanol and ethyl acetate (1:1) afforded a yellow crystalline product of (Z)Methyl-4-((3-((2,5- dioxoimidazolidin-4-ylidene)methyl)-1H-indol-1-yl)methyl)benzoate that was suitable for X-ray analysis. ¹H NMR (DMSO d₆): δ 3.81 (s, 3H), 5.54 (s, 2H), 6.74 (s, 1H), 7.15–7.23 (m, 2H), 7.40–7.42 (d, 2H), 7.50–7.52 (d, 1H), 7.79–7.81 (d, 1H), 7.91–7.93 (d, 2H), 8.32 (s, 1H), 10.15 (bs, 1H), 11.06 (bs, 1H); ¹³C NMR (DMSO d₆): δ 49.52, 52.2, 101.44, 109.26, 111.26, 119.22, 121.35, 123.44, 124.01, 127.29, 128.95, 129.35, 131.23, 136.28, 142.64, 155.93, 165.85, 167.12.

Computing details top

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 (Sheldrick, 2008) and local procedures.

Figures top

Fig. 1. A view of the molecule with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(Z)-Methyl 4-({3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-1H- indol-1-yl}methyl)benzoate top

Crystal data top

C₂₁H₁₇N₃O₄	Z = 2
M_r = 375.38	F(000) = 392
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0697P)² + 0.3949P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3997 reflections	Δρ_max = 0.48 e Å⁻³
255 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₁₇N₃O₄	γ = 104.4242 (9)°
M_r = 375.38	V = 883.25 (2) Å³
Triclinic, P1	Z = 2
a = 7.6390 (1) Å	Mo Kα radiation
b = 8.0013 (1) Å	µ = 0.10 mm⁻¹
c = 15.0405 (3) Å	T = 90 K
α = 91.9853 (9)°	0.25 × 0.22 × 0.15 mm
β = 96.2291 (9)°

Data collection top

Nonius KappaCCD diffractometer	3997 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	3595 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.985	R_int = 0.015
19513 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.07	Δρ_max = 0.48 e Å⁻³
3997 reflections	Δρ_min = −0.34 e Å⁻³
255 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₃O₄
M_r	375.38
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	7.6390 (1), 8.0013 (1), 15.0405 (3)
α, β, γ (°)	91.9853 (9), 96.2291 (9), 104.4242 (9)
V (Å³)	883.25 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.22 × 0.15

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.976, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	19513, 3997, 3595
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.07
No. of reflections	3997
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.34

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and local procedures.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12ⁱ	0.88	2.11	2.9658 (15)	163.3
N13—H13···O22ⁱⁱ	0.88	2.29	2.9699 (15)	134.0

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

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA104457 (to PAC) and by NSF MRI grant CHE 0319176 (to SP).

References

Mason, M. R., Barnard, T. S., Segla, M. F., Xie, B. & Kirschbaum, K. (2003). J. Chem. Crystallogr. 33, 531–540. Web of Science CSD CrossRef CAS Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sekhar, K. R., Crooks, P. A., Sonar, V. N., Friedman, D. B., Chan, J. Y., Meredith, M. J., Stames, J. H., Kelton, K. R., Summar, S. R., Sasi, S. & Freeman, M. L. (2003). Cancer Res. 63, 5636–5645. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Reddy, Y. T., Sekhar, K. R., Sowmya, S., Freeman, M. L. & Crooks, P. A. (2007). Bioorg. Med. Chem. Lett. 17, 6821–6824. Web of Science CrossRef PubMed CAS Google Scholar
Zarza, P. M., Gill, P., Díaz González, M. C., Martin Reyes, M. G., Arrieta, J. M., Nastopoulos, V., Germain, G. & Debaerdemaeker, T. (1988). Acta Cryst. C44, 678–681. CSD CrossRef CAS Web of Science 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 65| Part 1| January 2009| Pages o62-o63

doi:10.1107/S1600536808041020

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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