2-Methoxy-phenyl 2-{2-[1-methyl-5-(4-methyl-benzo-yl)pyrrol-2-yl]acetamido}acetate.

The title compound, amtolmetin guacil, C(24)H(24)N(2)O(5), is a new gastroprotective non-steroidal anti-inflammatory drug. In the crystal structure, the drug mol-ecule is linked into a one-dimensional structure along the c axis by weak N-H⋯O inter-actions between the amide groups. C-H⋯O and C-H⋯π inter-actions influence the packing.

Related literature

For background, see: Tubaro et al. (2000 ▶); Vippagunta et al. (2001 ▶).

Experimental

Crystal data

C24H24N2O5

M = 420.45

Orthorhombic,

a = 11.307 (3) Å

b = 19.768 (7) Å

c = 9.713 (3) Å

V = 2170.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Weissenberg IP diffractometer

Absorption correction: none

19812 measured reflections

2626 independent reflections

1938 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.109

S = 1.12

2626 reflections

284 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: TEXRAY (Molecular Structure Corporation, 1999 ▶); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020722/bv2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020722/bv2099Isup2.hkl

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

C24H24N2O5	F000 = 888
Mr = 420.45	Dx = 1.286 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2c-2n	Cell parameters from 19812 reflections
a = 11.307 (3) Å	θ = 3.5–27.5º
b = 19.768 (7) Å	µ = 0.09 mm−1
c = 9.713 (3) Å	T = 293 (2) K
V = 2170.9 (12) Å3	Block, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Rigaku Weissenberg IP diffractometer	1938 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.085
Monochromator: graphite	θmax = 27.5º
T = 293(2) K	θmin = 3.5º
scintillation counter scans	h = −14→14
Absorption correction: none	k = −25→25
19812 measured reflections	l = −12→12
2626 independent 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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.5426P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2626 reflections	Δρmax = 0.13 e Å−3
284 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0111 (12)

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
O1	−0.0274 (2)	0.40855 (14)	0.2773 (3)	0.0591 (8)
O2	0.1174 (2)	0.48242 (13)	0.4332 (4)	0.0637 (8)
O3	0.2659 (2)	0.40913 (14)	0.4028 (4)	0.0647 (9)
O4	0.4775 (2)	0.51742 (15)	0.4870 (3)	0.0595 (8)
O5	0.7830 (4)	0.75559 (16)	0.3571 (4)	0.0995 (13)
N1	0.4020 (2)	0.51066 (16)	0.2744 (3)	0.0481 (8)
H1	0.4147	0.5028	0.1864	0.058*
N2	0.6986 (2)	0.61548 (15)	0.3541 (3)	0.0438 (7)
C1	−0.1080 (4)	0.3716 (3)	0.1921 (5)	0.0747 (14)
H1A	−0.0888	0.3233	0.1960	0.112*
H1B	−0.1016	0.3876	0.0969	0.112*
H1C	−0.1890	0.3787	0.2252	0.112*
C2	−0.0308 (3)	0.39568 (19)	0.4136 (5)	0.0469 (9)
C3	−0.1055 (3)	0.35013 (19)	0.4785 (5)	0.0547 (11)
H3	−0.1590	0.3239	0.4251	0.066*
C4	−0.1032 (4)	0.3424 (2)	0.6190 (5)	0.0676 (13)
H4	−0.1552	0.3111	0.6620	0.081*
C5	−0.0266 (4)	0.3793 (3)	0.6973 (5)	0.0721 (13)
H5	−0.0254	0.3735	0.7944	0.086*
C6	0.0490 (4)	0.4250 (2)	0.6363 (5)	0.0678 (13)
H6	0.1021	0.4509	0.6907	0.081*
C7	0.0467 (3)	0.43263 (19)	0.4957 (5)	0.0505 (10)
C8	0.2255 (3)	0.4638 (2)	0.3893 (4)	0.0464 (9)
C9	0.2833 (3)	0.5239 (2)	0.3221 (4)	0.0538 (10)
H9A	0.2344	0.5385	0.2429	0.065*
H9B	0.2856	0.5618	0.3888	0.065*
C10	0.4926 (3)	0.51018 (18)	0.3624 (4)	0.0448 (9)
C11	0.6148 (3)	0.5008 (2)	0.3026 (4)	0.0478 (10)
H11A	0.6407	0.4533	0.3153	0.057*
H11B	0.6135	0.5106	0.2027	0.057*
C12	0.6995 (3)	0.54758 (17)	0.3735 (4)	0.0402 (8)
C13	0.7776 (3)	0.53269 (19)	0.4760 (4)	0.0456 (9)
H13	0.7976	0.4888	0.5084	0.055*
C14	0.8228 (3)	0.59397 (19)	0.5247 (4)	0.0486 (10)
H14	0.8779	0.5993	0.5978	0.058*
C15	0.7734 (3)	0.64510 (18)	0.4483 (4)	0.0458 (9)
C16	0.6281 (4)	0.6504 (2)	0.2510 (4)	0.0677 (13)
H16A	0.6737	0.6544	0.1656	0.102*
H16B	0.6074	0.6956	0.2847	0.102*
H16C	0.5556	0.6246	0.2332	0.102*
C17	0.7972 (4)	0.7178 (2)	0.4555 (4)	0.0581 (11)
C18	0.8422 (3)	0.74440 (19)	0.5879 (4)	0.0483 (9)
C19	0.8074 (3)	0.71810 (18)	0.7124 (4)	0.0482 (10)
H19	0.7539	0.6811	0.7145	0.058*
C20	0.8493 (3)	0.74480 (19)	0.8353 (4)	0.0512 (10)
H20	0.8244	0.7258	0.9204	0.061*
C21	0.9197 (4)	0.79965 (19)	0.5888 (5)	0.0576 (11)
H21	0.9435	0.8195	0.5042	0.069*
C22	0.9615 (3)	0.8255 (2)	0.7100 (5)	0.0580 (11)
H22	1.0152	0.8624	0.7080	0.070*
C23	0.9273 (3)	0.79901 (19)	0.8349 (5)	0.0529 (10)
C24	0.9719 (5)	0.8269 (2)	0.9692 (5)	0.0820 (16)
H24A	1.0546	0.8408	0.9588	0.123*
H24B	0.9662	0.7920	1.0406	0.123*
H24C	0.9240	0.8661	0.9958	0.123*

	U11	U22	U33	U12	U13	U23
O1	0.0588 (17)	0.0615 (18)	0.0569 (18)	−0.0087 (14)	0.0102 (15)	−0.0022 (15)
O2	0.0390 (13)	0.0507 (15)	0.101 (2)	−0.0013 (12)	0.0066 (16)	−0.0015 (17)
O3	0.0476 (15)	0.0512 (17)	0.096 (2)	0.0026 (13)	0.0111 (16)	−0.0020 (16)
O4	0.0488 (15)	0.091 (2)	0.0383 (16)	−0.0072 (15)	0.0047 (13)	−0.0114 (16)
O5	0.164 (3)	0.065 (2)	0.069 (2)	−0.033 (2)	−0.042 (3)	0.0247 (19)
N1	0.0393 (17)	0.064 (2)	0.0406 (17)	−0.0050 (15)	−0.0003 (15)	−0.0036 (16)
N2	0.0472 (16)	0.0503 (18)	0.0339 (16)	−0.0026 (14)	−0.0076 (15)	0.0020 (15)
C1	0.058 (3)	0.102 (4)	0.064 (3)	−0.004 (3)	−0.003 (3)	−0.008 (3)
C2	0.040 (2)	0.043 (2)	0.057 (3)	0.0051 (17)	0.011 (2)	−0.0051 (19)
C3	0.048 (2)	0.043 (2)	0.073 (3)	−0.0034 (18)	0.012 (2)	−0.007 (2)
C4	0.064 (3)	0.063 (3)	0.076 (4)	0.006 (2)	0.024 (3)	0.012 (3)
C5	0.071 (3)	0.087 (3)	0.059 (3)	0.013 (3)	0.001 (3)	0.012 (3)
C6	0.052 (3)	0.079 (3)	0.072 (3)	0.002 (2)	−0.008 (2)	−0.009 (3)
C7	0.039 (2)	0.045 (2)	0.067 (3)	0.0008 (18)	0.007 (2)	0.001 (2)
C8	0.0365 (18)	0.050 (2)	0.052 (2)	−0.0055 (18)	−0.0036 (18)	−0.0102 (19)
C9	0.042 (2)	0.061 (2)	0.059 (3)	0.0005 (19)	−0.006 (2)	0.002 (2)
C10	0.046 (2)	0.050 (2)	0.039 (2)	−0.0093 (17)	0.0015 (19)	−0.0059 (19)
C11	0.045 (2)	0.062 (2)	0.036 (2)	−0.0069 (18)	−0.0002 (17)	−0.0103 (18)
C12	0.0370 (17)	0.050 (2)	0.0338 (19)	−0.0018 (16)	0.0052 (16)	−0.0062 (17)
C13	0.043 (2)	0.046 (2)	0.048 (2)	0.0054 (17)	−0.0036 (19)	−0.0019 (18)
C14	0.042 (2)	0.055 (2)	0.048 (2)	−0.0012 (18)	−0.0135 (18)	−0.002 (2)
C15	0.050 (2)	0.048 (2)	0.040 (2)	−0.0054 (17)	−0.0137 (19)	−0.0016 (18)
C16	0.077 (3)	0.071 (3)	0.055 (3)	−0.003 (2)	−0.029 (2)	0.015 (2)
C17	0.071 (3)	0.052 (2)	0.052 (3)	−0.008 (2)	−0.013 (2)	0.008 (2)
C18	0.053 (2)	0.038 (2)	0.054 (2)	−0.0030 (18)	−0.007 (2)	−0.001 (2)
C19	0.048 (2)	0.0395 (19)	0.058 (3)	−0.0020 (16)	−0.012 (2)	0.000 (2)
C20	0.057 (2)	0.046 (2)	0.051 (2)	0.0035 (19)	−0.007 (2)	−0.004 (2)
C21	0.060 (2)	0.043 (2)	0.070 (3)	−0.007 (2)	−0.002 (2)	0.003 (2)
C22	0.057 (2)	0.043 (2)	0.075 (3)	−0.0097 (18)	−0.004 (3)	−0.011 (2)
C23	0.052 (2)	0.043 (2)	0.063 (3)	0.0061 (18)	−0.021 (2)	−0.012 (2)
C24	0.098 (4)	0.069 (3)	0.079 (3)	−0.003 (3)	−0.034 (3)	−0.024 (3)

O1—C2	1.349 (5)	C10—C11	1.511 (5)
O1—C1	1.431 (5)	C11—C12	1.499 (5)
O2—C8	1.346 (4)	C11—H11A	0.9900
O2—C7	1.406 (5)	C11—H11B	0.9900
O3—C8	1.181 (4)	C12—C13	1.363 (5)
O4—C10	1.230 (4)	C13—C14	1.397 (5)
O5—C17	1.223 (5)	C13—H13	0.9500
N1—C10	1.334 (5)	C14—C15	1.372 (5)
N1—C9	1.443 (4)	C14—H14	0.9500
N1—H1	0.8800	C15—C17	1.464 (5)
N2—C12	1.355 (4)	C16—H16A	0.9800
N2—C15	1.377 (4)	C16—H16B	0.9800
N2—C16	1.454 (5)	C16—H16C	0.9800
C1—H1A	0.9800	C17—C18	1.479 (6)
C1—H1B	0.9800	C18—C19	1.374 (5)
C1—H1C	0.9800	C18—C21	1.400 (5)
C2—C3	1.386 (6)	C19—C20	1.388 (6)
C2—C7	1.392 (6)	C19—H19	0.9500
C3—C4	1.374 (6)	C20—C23	1.388 (5)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.365 (7)	C21—C22	1.367 (6)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.377 (7)	C22—C23	1.376 (6)
C5—H5	0.9500	C22—H22	0.9500
C6—C7	1.374 (6)	C23—C24	1.504 (6)
C6—H6	0.9500	C24—H24A	0.9800
C8—C9	1.505 (5)	C24—H24B	0.9800
C9—H9A	0.9900	C24—H24C	0.9800
C9—H9B	0.9900
C2—O1—C1	116.9 (3)	C10—C11—H11B	109.8
C8—O2—C7	117.5 (3)	H11A—C11—H11B	108.2
C10—N1—C9	120.6 (3)	N2—C12—C13	108.7 (3)
C10—N1—H1	119.7	N2—C12—C11	122.9 (3)
C9—N1—H1	119.7	C13—C12—C11	128.0 (3)
C12—N2—C15	108.9 (3)	C12—C13—C14	107.3 (3)
C12—N2—C16	124.7 (3)	C12—C13—H13	126.4
C15—N2—C16	126.4 (3)	C14—C13—H13	126.4
O1—C1—H1A	109.5	C15—C14—C13	107.9 (3)
O1—C1—H1B	109.5	C15—C14—H14	126.1
H1A—C1—H1B	109.5	C13—C14—H14	126.1
O1—C1—H1C	109.5	C14—C15—N2	107.2 (3)
H1A—C1—H1C	109.5	C14—C15—C17	128.5 (3)
H1B—C1—H1C	109.5	N2—C15—C17	124.2 (3)
O1—C2—C3	125.9 (4)	N2—C16—H16A	109.5
O1—C2—C7	116.4 (4)	N2—C16—H16B	109.5
C3—C2—C7	117.7 (4)	H16A—C16—H16B	109.5
C4—C3—C2	120.8 (4)	N2—C16—H16C	109.5
C4—C3—H3	119.6	H16A—C16—H16C	109.5
C2—C3—H3	119.6	H16B—C16—H16C	109.5
C5—C4—C3	120.4 (5)	O5—C17—C15	122.5 (4)
C5—C4—H4	119.8	O5—C17—C18	120.5 (4)
C3—C4—H4	119.8	C15—C17—C18	117.0 (3)
C4—C5—C6	120.3 (5)	C19—C18—C21	117.9 (4)
C4—C5—H5	119.9	C19—C18—C17	122.2 (3)
C6—C5—H5	119.9	C21—C18—C17	119.9 (4)
C7—C6—C5	119.3 (5)	C18—C19—C20	121.0 (3)
C7—C6—H6	120.4	C18—C19—H19	119.5
C5—C6—H6	120.4	C20—C19—H19	119.5
C6—C7—C2	121.5 (4)	C23—C20—C19	120.5 (4)
C6—C7—O2	119.7 (4)	C23—C20—H20	119.8
C2—C7—O2	118.6 (4)	C19—C20—H20	119.8
O3—C8—O2	124.5 (4)	C22—C21—C18	120.9 (4)
O3—C8—C9	127.1 (3)	C22—C21—H21	119.5
O2—C8—C9	108.4 (3)	C18—C21—H21	119.5
N1—C9—C8	113.5 (3)	C21—C22—C23	121.3 (4)
N1—C9—H9A	108.9	C21—C22—H22	119.4
C8—C9—H9A	108.9	C23—C22—H22	119.4
N1—C9—H9B	108.9	C22—C23—C20	118.4 (4)
C8—C9—H9B	108.9	C22—C23—C24	122.1 (4)
H9A—C9—H9B	107.7	C20—C23—C24	119.6 (4)
O4—C10—N1	121.5 (4)	C23—C24—H24A	109.5
O4—C10—C11	121.3 (3)	C23—C24—H24B	109.5
N1—C10—C11	117.2 (3)	H24A—C24—H24B	109.5
C12—C11—C10	109.4 (3)	C23—C24—H24C	109.5
C12—C11—H11A	109.8	H24A—C24—H24C	109.5
C10—C11—H11A	109.8	H24B—C24—H24C	109.5
C12—C11—H11B	109.8

D—H···A	D—H (Å)	H···A (Å)	D···A (Å)	D—H···A (°)
N1—H1···O4i	0.88	2.32	3.1564	157
C11—H11B···O4i	0.99	2.40	3.2586	145
C24—H24A···O3ii	0.98	2.50	3.4418	162
C14—H14··· O1iii	0.95	2.43	3.3722	170
C19—H19··· O3iii	0.95	2.56	3.2300	127
C13—H13··· Cg1iv	0.95	2.85	3.6961	150

Table 1

Hydrogen-bonding geometry (Å, °)

Cg1 is the centroid of the C2/C3–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.88	2.32	3.1564	157
C11—H11B⋯O4i	0.99	2.40	3.2586	145
C24—H24A⋯O3ii	0.98	2.50	3.4418	162
C14—H14⋯ O1iii	0.95	2.43	3.3722	170
C19—H19⋯ O3iii	0.95	2.56	3.2300	127
C13—H13⋯ Cg1iv	0.95	2.85	3.6961	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .