Indomethacin methyl ester

Trask, A.V.; Shan, N.; Jones, W.; Motherwell, W.D.S.

doi:10.1107/S1600536804004453

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 4| April 2004| Pages o508-o509

https://doi.org/10.1107/S1600536804004453

Indomethacin methyl ester

Andrew V. Trask,^a ^* Ning Shan,^b William Jones ^a and W. D. Sam Motherwell ^c

^aDepartment of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, England, and Pfizer Institute for Pharmaceutical Materials Science, ^bInstitute of Chemical and Engineering Sciences, Ayer Rajah Crescent, Block 28, Unit 02-08, Singapore 139959, and Pfizer Institute for Pharmaceutical Materials Science, and ^cCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England
^*Correspondence e-mail: avt21@cam.ac.uk

(Received 30 January 2004; accepted 26 February 2004; online 6 March 2004)

The cystal structure of the title compound [systematic name: methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate], C₂₀H₁₈ClNO₄, exhibits a short axis similar to another indomethacin analogue. Also observed in the structure is a packing of molecules influenced by weak C—H⋯O hydrogen bonds.

Comment

As part of an investigation into the crystallization of pharmaceutical compounds, the crystal structures of indomethacin derivatives are of interest. Numerous studies have been reported on various crystal structures of the drug indomethacin (γ-form: Kistenmacher & Marsh, 1972 ; α-form: Chen et al., 2002 ; t-butanol and methanol solvates: Joshi et al., 1998 ). In contrast, the structure of its methyl ester, (I), has not been reported to date. We report here its crystal structure and describe the intermolecular interactions involved.

The asymmetric unit of (I) comprises one molecule (Fig. 1). Although the crystal structure of the indomethacin methyl ester differs significantly from that of the parent carboxylic acid, it bears some similarity to the structure of another indomethacin derivative, iodoindomethacin (Loll et al., 1996 ). Both crystal structures exhibit a relatively short axis [4.8326 (1) Å for the methyl ester derivative versus 4.7250 (10) Å for the iodo derivative]. In addition, both crystal structures show a halogen contact to a carbonyl O atom [Cl1⋯O4 = 3.575 (2) Å versus I1⋯O4 = 3.162 (5) Å].

In the absence of the carboxylic acid group of indomethacin, no strong O—H⋯O hydrogen bonding can be expected in the crystal structure of the methyl ester. Instead, C—H⋯O hydrogen bonds form a three-dimensional supramolecular network, as shown in Fig. 2. Hydrogen-bond distances and angles are provided in Table 1.

Figure 1
Molecular unit showing displacement ellipsoids at the 50% probability level.

Figure 2
Projection on to (010), showing the packing involving C—H⋯O interactions. The intermolecular C9—H9A⋯O4(x, y − 1, z) hydrogen bond projects parallel to the b axis.

Experimental

Indomethacin and anhydrous benzenesulfonic acid were obtained from Sigma–Aldrich and were used as received. Indomethacin (130 mg, 0.364 mmol) and benzensulfonic acid (115 mg, 0.727 mmol) were dissolved in methanol with heating. Crystals precipitated as the solution cooled to room temperature and were immediately isolated and dried.

Crystal data

C₂₀H₁₈ClNO₄
M_r = 371.82
Monoclinic, P2₁/n
a = 19.0206 (5) Å
b = 4.8326 (1) Å
c = 19.3092 (8) Å
β = 97.739 (1)°
V = 1758.72 (9) Å³
Z = 4
D_x = 1.404 Mg m⁻³
Mo Kα radiation
Cell parameters from 6724 reflections
θ = 1.0–25.0°
μ = 0.24 mm⁻¹
T = 180 (2) K
Needle, yellow
0.46 × 0.07 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
ω and φ scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.946, T_max = 0.985
10 009 measured reflections
3086 independent reflections
2410 reflections with I > 2σ(I)
R_int = 0.035
θ_max = 25.0°
h = −22 → 22
k = −5 → 5
l = −22 → 23

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.117
S = 1.04
3086 reflections
238 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0481P)² + 1.0445P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.002
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1ⁱ	0.95	2.34	3.260 (3)	162
C3—H3⋯O1ⁱⁱ	0.95	2.59	3.480 (3)	156
C9—H9A⋯O4ⁱⁱⁱ	0.99	2.62	3.565 (3)	160
C15—H15⋯O2^iv	0.95	2.48	3.419 (2)	170
Symmetry codes: (i) 2-x,1-y,2-z; (ii) 2-x,-y,2-z; (iii) x,y-1,z; (iv) $[{\script{5\over 2}}-x,y-{\script{1\over 2}},{\script{3\over 2}}-z]$ .

All H atoms were placed geometrically and treated using a riding model. The U_iso values for methyl H atoms were fixed at 1.5U_eq of the carrier atom. For all other H atoms, U_iso(H) = 1.2U_eq(carrier atom). The C—H distances of methyl groups were fixed at 0.98 Å; all other C—H distances were fixed at 0.95 Å.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804004453/om6215sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804004453/om6215Isup2.hkl

Computing details top

Data collection: Collect (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: XP (Sheldrick, 1993) and Diamond (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

Methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]acetate top

Crystal data top

C₂₀H₁₈ClNO₄	D_x = 1.404 Mg m⁻³
M_r = 371.82	Melting point: not measured K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 19.0206 (5) Å	Cell parameters from 6724 reflections
b = 4.8326 (1) Å	θ = 1.0–25.0°
c = 19.3092 (8) Å	µ = 0.24 mm⁻¹
β = 97.739 (1)°	T = 180 K
V = 1758.72 (9) Å³	Needle, yellow
Z = 4	0.46 × 0.07 × 0.05 mm
F(000) = 776

Data collection top

Nonius KappaCCD diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 25.0°, θ_min = 3.6°
Absorption correction: multi-scan Sortav (Blessing, 1995)	h = −22→22
T_min = 0.946, T_max = 0.985	k = −5→5
10009 measured reflections	l = −22→23

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0481P)² + 1.0445P] where P = (F_o² + 2F_c²)/3
3086 reflections	(Δ/σ)_max = 0.002
238 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

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
Cl1	0.65787 (4)	−0.17803 (18)	0.86754 (4)	0.0706 (3)
O1	0.98228 (10)	0.2360 (4)	0.95373 (9)	0.0550 (5)
O2	1.24396 (8)	0.8532 (3)	0.84051 (8)	0.0436 (4)
O3	1.09430 (9)	0.0986 (3)	0.56653 (8)	0.0458 (4)
O4	1.02616 (11)	0.3946 (4)	0.61588 (9)	0.0613 (5)
N1	1.00383 (9)	0.2127 (3)	0.84188 (9)	0.0299 (4)
C1	0.96165 (12)	0.1665 (5)	0.89405 (11)	0.0355 (5)
C2	0.88813 (12)	0.0526 (5)	0.87820 (11)	0.0354 (5)
C3	0.86722 (13)	−0.1409 (5)	0.92464 (12)	0.0431 (6)
H3	0.9013	−0.2196	0.9596	0.052*
C4	0.79675 (14)	−0.2190 (5)	0.92002 (13)	0.0498 (7)
H4	0.7824	−0.3554	0.9507	0.060*
C5	0.74766 (13)	−0.0969 (5)	0.87051 (13)	0.0451 (6)
C6	0.76742 (13)	0.0955 (5)	0.82406 (13)	0.0451 (6)
H6	0.7329	0.1779	0.7901	0.054*
C7	0.83837 (12)	0.1670 (5)	0.82758 (12)	0.0404 (6)
H7	0.8529	0.2953	0.7950	0.049*
C8	0.95660 (12)	−0.1570 (5)	0.75198 (12)	0.0377 (5)
H8A	0.9761	−0.2628	0.7156	0.057*
H8B	0.9113	−0.0739	0.7323	0.057*
H8C	0.9491	−0.2806	0.7905	0.057*
C9	1.09125 (12)	0.0424 (4)	0.68596 (10)	0.0335 (5)
H9A	1.0756	−0.1523	0.6792	0.040*
H9B	1.1438	0.0434	0.6931	0.040*
C10	1.06587 (12)	0.2015 (4)	0.62062 (11)	0.0339 (5)
C11	1.00736 (11)	0.0656 (4)	0.77853 (10)	0.0307 (5)
C12	1.26800 (13)	1.0394 (5)	0.89591 (13)	0.0465 (6)
H12A	1.3122	1.1275	0.8866	0.070*
H12B	1.2765	0.9371	0.9401	0.070*
H12C	1.2318	1.1815	0.8991	0.070*
C13	1.06544 (11)	0.1519 (4)	0.75071 (10)	0.0302 (5)
C14	1.10167 (11)	0.3605 (4)	0.79639 (10)	0.0286 (5)
C15	1.16259 (11)	0.5171 (4)	0.79317 (11)	0.0321 (5)
H15	1.1895	0.4955	0.7555	0.039*
C16	1.18318 (11)	0.7055 (4)	0.84620 (11)	0.0325 (5)
C17	1.14376 (11)	0.7377 (4)	0.90166 (11)	0.0332 (5)
H17	1.1586	0.8689	0.9373	0.040*
C18	1.08335 (11)	0.5814 (4)	0.90559 (11)	0.0332 (5)
H18	1.0564	0.6038	0.9432	0.040*
C19	1.06351 (11)	0.3918 (4)	0.85293 (10)	0.0289 (5)
C20	1.07509 (17)	0.2359 (7)	0.50019 (13)	0.0614 (8)
H20A	1.0996	0.1470	0.4646	0.092*
H20B	1.0890	0.4311	0.5045	0.092*
H20C	1.0237	0.2227	0.4865	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0484 (4)	0.0997 (6)	0.0658 (5)	−0.0277 (4)	0.0158 (3)	−0.0150 (4)
O1	0.0611 (11)	0.0762 (13)	0.0302 (10)	−0.0255 (10)	0.0156 (8)	−0.0075 (9)
O2	0.0426 (10)	0.0463 (10)	0.0448 (10)	−0.0091 (7)	0.0166 (8)	−0.0041 (7)
O3	0.0578 (11)	0.0550 (10)	0.0263 (8)	0.0105 (8)	0.0117 (7)	−0.0011 (7)
O4	0.0880 (14)	0.0593 (12)	0.0367 (10)	0.0352 (11)	0.0081 (9)	0.0053 (8)
N1	0.0325 (10)	0.0326 (10)	0.0253 (9)	0.0025 (7)	0.0065 (7)	0.0004 (7)
C1	0.0416 (13)	0.0373 (12)	0.0291 (12)	−0.0008 (10)	0.0097 (10)	0.0004 (9)
C2	0.0394 (13)	0.0363 (12)	0.0324 (12)	−0.0015 (10)	0.0124 (10)	−0.0048 (10)
C3	0.0472 (14)	0.0451 (14)	0.0381 (13)	−0.0045 (11)	0.0096 (11)	0.0023 (11)
C4	0.0604 (17)	0.0491 (15)	0.0429 (15)	−0.0159 (12)	0.0181 (13)	−0.0009 (12)
C5	0.0420 (14)	0.0543 (15)	0.0408 (14)	−0.0127 (11)	0.0123 (11)	−0.0147 (12)
C6	0.0422 (14)	0.0513 (15)	0.0414 (14)	0.0002 (11)	0.0043 (11)	−0.0049 (11)
C7	0.0424 (14)	0.0411 (13)	0.0392 (14)	−0.0013 (10)	0.0109 (11)	0.0019 (10)
C8	0.0403 (13)	0.0369 (12)	0.0358 (13)	0.0031 (10)	0.0046 (10)	−0.0046 (10)
C9	0.0419 (13)	0.0329 (12)	0.0265 (11)	0.0082 (9)	0.0075 (9)	−0.0016 (9)
C10	0.0385 (12)	0.0353 (13)	0.0286 (12)	0.0004 (10)	0.0067 (10)	−0.0044 (9)
C11	0.0369 (12)	0.0286 (11)	0.0261 (11)	0.0074 (9)	0.0028 (9)	0.0009 (8)
C12	0.0437 (14)	0.0465 (14)	0.0492 (15)	−0.0077 (11)	0.0063 (12)	−0.0006 (12)
C13	0.0385 (12)	0.0286 (11)	0.0234 (11)	0.0089 (9)	0.0035 (9)	0.0019 (8)
C14	0.0335 (12)	0.0297 (11)	0.0231 (11)	0.0083 (9)	0.0054 (9)	0.0042 (8)
C15	0.0363 (12)	0.0338 (12)	0.0284 (12)	0.0093 (9)	0.0124 (9)	0.0041 (9)
C16	0.0340 (12)	0.0313 (12)	0.0332 (12)	0.0033 (9)	0.0078 (9)	0.0065 (9)
C17	0.0394 (12)	0.0317 (11)	0.0291 (12)	0.0008 (9)	0.0063 (10)	−0.0016 (9)
C18	0.0380 (12)	0.0361 (12)	0.0272 (11)	0.0026 (9)	0.0104 (9)	−0.0012 (9)
C19	0.0318 (11)	0.0293 (11)	0.0260 (11)	0.0039 (8)	0.0054 (9)	0.0028 (9)
C20	0.078 (2)	0.081 (2)	0.0256 (13)	0.0024 (16)	0.0099 (13)	0.0064 (13)

Geometric parameters (Å, º) top

Cl1—C5	1.746 (2)	C8—H8B	0.9800
O1—C1	1.214 (3)	C8—H8C	0.9800
O2—C16	1.376 (3)	C9—C13	1.500 (3)
O2—C12	1.425 (3)	C9—C10	1.501 (3)
O3—C10	1.335 (3)	C9—H9A	0.9900
O3—C20	1.445 (3)	C9—H9B	0.9900
O4—C10	1.196 (3)	C11—C13	1.357 (3)
N1—C1	1.388 (3)	C12—H12A	0.9800
N1—C19	1.420 (3)	C12—H12B	0.9800
N1—C11	1.424 (3)	C12—H12C	0.9800
C1—C2	1.496 (3)	C13—C14	1.451 (3)
C2—C7	1.381 (3)	C14—C15	1.393 (3)
C2—C3	1.390 (3)	C14—C19	1.398 (3)
C3—C4	1.384 (3)	C15—C16	1.386 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.376 (4)	C16—C17	1.396 (3)
C4—H4	0.9500	C17—C18	1.386 (3)
C5—C6	1.379 (4)	C17—H17	0.9500
C6—C7	1.386 (3)	C18—C19	1.383 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—H7	0.9500	C20—H20A	0.9800
C8—C11	1.490 (3)	C20—H20B	0.9800
C8—H8A	0.9800	C20—H20C	0.9800

C16—O2—C12	117.11 (17)	O4—C10—C9	126.3 (2)
C10—O3—C20	116.21 (19)	O3—C10—C9	110.39 (18)
C1—N1—C19	121.17 (17)	C13—C11—N1	108.76 (18)
C1—N1—C11	129.92 (18)	C13—C11—C8	127.59 (19)
C19—N1—C11	107.69 (16)	N1—C11—C8	123.55 (18)
O1—C1—N1	120.0 (2)	O2—C12—H12A	109.5
O1—C1—C2	118.03 (19)	O2—C12—H12B	109.5
N1—C1—C2	121.79 (19)	H12A—C12—H12B	109.5
C7—C2—C3	119.8 (2)	O2—C12—H12C	109.5
C7—C2—C1	122.0 (2)	H12A—C12—H12C	109.5
C3—C2—C1	117.2 (2)	H12B—C12—H12C	109.5
C4—C3—C2	120.0 (2)	C11—C13—C14	108.55 (18)
C4—C3—H3	120.0	C11—C13—C9	126.6 (2)
C2—C3—H3	120.0	C14—C13—C9	124.73 (19)
C5—C4—C3	119.2 (2)	C15—C14—C19	119.89 (19)
C5—C4—H4	120.4	C15—C14—C13	132.90 (19)
C3—C4—H4	120.4	C19—C14—C13	107.21 (18)
C4—C5—C6	121.5 (2)	C16—C15—C14	118.56 (18)
C4—C5—Cl1	119.7 (2)	C16—C15—H15	120.7
C6—C5—Cl1	118.8 (2)	C14—C15—H15	120.7
C5—C6—C7	119.0 (2)	O2—C16—C15	116.01 (18)
C5—C6—H6	120.5	O2—C16—C17	123.2 (2)
C7—C6—H6	120.5	C15—C16—C17	120.8 (2)
C2—C7—C6	120.3 (2)	C18—C17—C16	121.1 (2)
C2—C7—H7	119.8	C18—C17—H17	119.5
C6—C7—H7	119.8	C16—C17—H17	119.5
C11—C8—H8A	109.5	C19—C18—C17	117.84 (19)
C11—C8—H8B	109.5	C19—C18—H18	121.1
H8A—C8—H8B	109.5	C17—C18—H18	121.1
C11—C8—H8C	109.5	C18—C19—C14	121.80 (19)
H8A—C8—H8C	109.5	C18—C19—N1	130.35 (19)
H8B—C8—H8C	109.5	C14—C19—N1	107.77 (17)
C13—C9—C10	114.56 (17)	O3—C20—H20A	109.5
C13—C9—H9A	108.6	O3—C20—H20B	109.5
C10—C9—H9A	108.6	H20A—C20—H20B	109.5
C13—C9—H9B	108.6	O3—C20—H20C	109.5
C10—C9—H9B	108.6	H20A—C20—H20C	109.5
H9A—C9—H9B	107.6	H20B—C20—H20C	109.5
O4—C10—O3	123.3 (2)

C19—N1—C1—O1	−13.8 (3)	N1—C11—C13—C9	176.99 (18)
C11—N1—C1—O1	152.0 (2)	C8—C11—C13—C9	0.6 (3)
C19—N1—C1—C2	161.21 (19)	C10—C9—C13—C11	94.3 (3)
C11—N1—C1—C2	−33.0 (3)	C10—C9—C13—C14	−89.3 (2)
O1—C1—C2—C7	123.7 (2)	C11—C13—C14—C15	−179.5 (2)
N1—C1—C2—C7	−51.4 (3)	C9—C13—C14—C15	3.5 (3)
O1—C1—C2—C3	−44.9 (3)	C11—C13—C14—C19	0.9 (2)
N1—C1—C2—C3	140.0 (2)	C9—C13—C14—C19	−176.05 (18)
C7—C2—C3—C4	0.1 (3)	C19—C14—C15—C16	−1.1 (3)
C1—C2—C3—C4	169.0 (2)	C13—C14—C15—C16	179.3 (2)
C2—C3—C4—C5	−2.0 (4)	C12—O2—C16—C15	−177.32 (19)
C3—C4—C5—C6	1.9 (4)	C12—O2—C16—C17	2.3 (3)
C3—C4—C5—Cl1	−176.15 (19)	C14—C15—C16—O2	179.62 (18)
C4—C5—C6—C7	0.0 (4)	C14—C15—C16—C17	0.0 (3)
Cl1—C5—C6—C7	178.05 (18)	O2—C16—C17—C18	−179.13 (19)
C3—C2—C7—C6	1.8 (3)	C15—C16—C17—C18	0.5 (3)
C1—C2—C7—C6	−166.5 (2)	C16—C17—C18—C19	0.2 (3)
C5—C6—C7—C2	−1.8 (4)	C17—C18—C19—C14	−1.4 (3)
C20—O3—C10—O4	0.6 (3)	C17—C18—C19—N1	−177.6 (2)
C20—O3—C10—C9	−179.1 (2)	C15—C14—C19—C18	1.9 (3)
C13—C9—C10—O4	−2.9 (3)	C13—C14—C19—C18	−178.48 (19)
C13—C9—C10—O3	176.79 (19)	C15—C14—C19—N1	178.81 (17)
C1—N1—C11—C13	−168.3 (2)	C13—C14—C19—N1	−1.5 (2)
C19—N1—C11—C13	−1.1 (2)	C1—N1—C19—C18	−13.2 (3)
C1—N1—C11—C8	8.3 (3)	C11—N1—C19—C18	178.2 (2)
C19—N1—C11—C8	175.50 (19)	C1—N1—C19—C14	170.21 (18)
N1—C11—C13—C14	0.1 (2)	C11—N1—C19—C14	1.6 (2)
C8—C11—C13—C14	−176.28 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.95	2.34	3.260 (3)	162
C3—H3···O1ⁱⁱ	0.95	2.59	3.480 (3)	156
C9—H9A···O4ⁱⁱⁱ	0.99	2.62	3.565 (3)	160
C15—H15···O2^iv	0.95	2.48	3.419 (2)	170

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+2; (iii) x, y−1, z; (iv) −x+5/2, y−1/2, −z+3/2.

Acknowledgements

The authors are grateful for funding from the Pfizer Institute for Pharmaceutical Materials Science at the University of Cambridge. We thank Dr J. E. Davies for the data collection.

References

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Volume 60| Part 4| April 2004| Pages o508-o509

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

Indomethacin methyl ester

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds