2-Methoxy­phenyl 2-{2-[1-methyl-5-(4-methyl­benzo­yl)pyrrol-2-yl]acetamido}acetate

Lou, B.-Y.; Guo, X.; Lin, Q.

doi:10.1107/S1600536808020722

2-Methoxyphenyl 2-{2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetamido}acetate

The title compound, amtolmetin guacil, C₂₄H₂₄N₂O₅, is a new gastroprotective non-steroidal anti-inflammatory drug. In the crystal structure, the drug molecule is linked into a one-dimensional structure along the c axis by weak N—H

O interactions between the amide groups. C—H

O and C—H

π interactions influence the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808020722/bv2099sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808020722/bv2099Isup2.hkl Contains datablock I

CCDC reference: 700465

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.069
wR factor = 0.109
Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               2626
           Count of symmetry unique reflns         2636
           Completeness (_total/calc)             99.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

A current focus of research in solid state drug design is to understand polymorphism at the molecular level (Vippagunta et al., 2001). Amtolmetin guacil is a new gastroprotective nonsteroidal anti-inflammatory drug (Tubaro et al., 2000). In this contribution, we report its crystal structure which is unknown till now.

In the crystal structure, there exist weak hydrogen bonding interactions (N1—H1···O4) between the amide group of amtolmetin guacil which connect drug molecules into a one-dimensional structure along c axis. There also exist weak C—H···O interactions within the one-dimensional structure (C11—H11B···O4; C14—H14···O1; C19—H19··· O3; Table 1). The C—H···O interactions and C—H···π interactions (C24—H24A···O3; C13—H13···Cg1; Table 1) give rise to the packing structure (Fig.2)

Related literature top

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

Experimental top

Amtolmetin guacil (105 mg, 0.25 mmol) was dissolved in ethanol (20 ml) and the solution was kept in air and after several days colorless crystals were obtained.

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP of (I) with 50% thermal ellipsoids.
	Fig. 2. The packing structure viewed along c axis. The dashed lines indicate C—H···O or C—H···π interactions

2-Methoxyphenyl 2-{2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetamido}acetate top

Crystal data top

C₂₄H₂₄N₂O₅	F(000) = 888
M_r = 420.45	D_x = 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 = 3.5–27.5°
b = 19.768 (7) Å	µ = 0.09 mm⁻¹
c = 9.713 (3) Å	T = 293 K
V = 2170.9 (12) Å³	Block, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku Weissenberg IP diffractometer	1938 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.085
Graphite monochromator	θ_max = 27.5°, θ_min = 3.5°
scintillation counter scans	h = −14→14
19812 measured reflections	k = −25→25
2626 independent reflections	l = −12→12

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)] = 0.068	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0337P)² + 0.5426P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2626 reflections	Δρ_max = 0.13 e Å⁻³
284 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₄N₂O₅	V = 2170.9 (12) Å³
M_r = 420.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.307 (3) Å	µ = 0.09 mm⁻¹
b = 19.768 (7) Å	T = 293 K
c = 9.713 (3) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku Weissenberg IP diffractometer	1938 reflections with I > 2σ(I)
19812 measured reflections	R_int = 0.085
2626 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1 restraint
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	Δρ_max = 0.13 e Å⁻³
2626 reflections	Δρ_min = −0.17 e Å⁻³
284 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 > 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₂O₅
M_r	420.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	11.307 (3), 19.768 (7), 9.713 (3)
V (Å³)	2170.9 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Weissenberg IP diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19812, 2626, 1938
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.109, 1.12
No. of reflections	2626
No. of parameters	284
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.17

Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Hydrogen-bonding geometry (A%, °). Cg1 is the centroid of the C2/C3–C7 ring. top

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··· Cg1^iv	0.95	2.85	3.6961	150

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

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2-Methoxy­phenyl 2-{2-[1-methyl-5-(4-methyl­benzo­yl)pyrrol-2-yl]acetamido}acetate

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2-Methoxyphenyl 2-{2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetamido}acetate