Ethopabate

In the title compound (systematic name: methyl 4-acetamido-2-ethoxy­benzoate), C₁₂H₁₅O₄N, inter­molecular N—H...O and C—H...O hydrogen bonds stabilize the crystal packing. An intra­molecular C—H...O hydrogen bond generates an S(6) motif.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.086
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.728     0.971
            Tmin(prime) and Tmax expected:      0.970     0.970
            RR(prime) =      0.750
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.75
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C7      ..       5.07 su

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

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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Methyl 4-acetamido-2-ethoxybenzoate

Crystal data

C12H15NO4	Dx = 1.326 Mg m^−3
Mr = 237.25	Melting point: 418 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9021 reflections
a = 15.110 (3) Å	θ = 2.4–22.0°
b = 9.2097 (19) Å	µ = 0.10 mm^−1
c = 17.084 (4) Å	T = 203 K
V = 2377.3 (9) Å^3	Block, colorless
Z = 8	0.30 × 0.30 × 0.30 mm
F(000) = 1008

Data collection

Bruker SMART CCD area-detector diffractometer	2091 independent reflections
Radiation source: fine-focus sealed tube	1355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→17
Tmin = 0.728, Tmax = 0.971	k = −10→10
9021 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0439P)^2] where P = (Fo^2 + 2Fc^2)/3
2091 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O3	0.38132 (8)	0.08959 (12)	0.31542 (6)	0.0392 (3)
O4	0.30300 (8)	0.60557 (13)	0.05830 (7)	0.0444 (4)
O2	0.44322 (8)	0.24055 (13)	0.43435 (7)	0.0455 (4)
C4	0.33747 (11)	0.36462 (18)	0.16466 (9)	0.0316 (4)
N1	0.28778 (9)	0.37022 (14)	0.09476 (8)	0.0359 (4)
H1	0.2634	0.2888	0.0806	0.043*
O1	0.54022 (9)	0.40742 (15)	0.39479 (8)	0.0603 (4)
C2	0.37946 (11)	0.21667 (17)	0.27550 (9)	0.0327 (4)
C7	0.47688 (13)	0.3315 (2)	0.38186 (10)	0.0389 (5)
C5	0.38674 (12)	0.47995 (19)	0.19352 (10)	0.0374 (5)
H5A	0.3903	0.5681	0.1660	0.045*
C1	0.42697 (11)	0.33435 (18)	0.30659 (9)	0.0323 (4)
C3	0.33510 (11)	0.23394 (18)	0.20500 (9)	0.0337 (4)
H3A	0.3029	0.1557	0.1842	0.040*
C11	0.27269 (11)	0.48442 (19)	0.04672 (10)	0.0343 (4)
C9	0.33888 (12)	−0.03556 (17)	0.28175 (10)	0.0386 (5)
H9B	0.3593	−0.0506	0.2279	0.058*
H9A	0.2745	−0.0225	0.2811	0.058*
C6	0.43028 (11)	0.46143 (19)	0.26373 (10)	0.0372 (5)
H6A	0.4639	0.5392	0.2834	0.045*
C10	0.36351 (12)	−0.16280 (19)	0.33190 (11)	0.0454 (5)
H10C	0.3445	−0.1452	0.3853	0.068*
H10B	0.4272	−0.1760	0.3308	0.068*
H10A	0.3348	−0.2495	0.3121	0.068*
C12	0.21656 (12)	0.4509 (2)	−0.02319 (10)	0.0478 (5)
H12C	0.2022	0.5403	−0.0504	0.072*
H12B	0.1624	0.4038	−0.0063	0.072*
H12A	0.2487	0.3868	−0.0582	0.072*
C8	0.49098 (13)	0.2309 (2)	0.50754 (10)	0.0536 (6)
H8C	0.4881	0.3235	0.5345	0.080*
H8B	0.5523	0.2066	0.4972	0.080*
H8A	0.4646	0.1562	0.5401	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0535 (8)	0.0309 (7)	0.0332 (7)	−0.0047 (6)	−0.0086 (6)	0.0029 (5)
O4	0.0548 (8)	0.0294 (7)	0.0489 (8)	−0.0007 (6)	−0.0016 (7)	0.0042 (6)
O2	0.0439 (8)	0.0619 (8)	0.0308 (7)	−0.0103 (7)	−0.0039 (6)	0.0030 (7)
C4	0.0343 (10)	0.0308 (10)	0.0298 (10)	0.0030 (8)	0.0020 (8)	−0.0012 (8)
N1	0.0463 (9)	0.0276 (8)	0.0337 (9)	−0.0031 (7)	−0.0033 (7)	0.0013 (7)
O1	0.0609 (10)	0.0720 (10)	0.0481 (9)	−0.0295 (8)	−0.0152 (7)	0.0064 (7)
C2	0.0379 (11)	0.0293 (10)	0.0309 (10)	0.0026 (8)	0.0029 (9)	−0.0003 (8)
C7	0.0414 (12)	0.0395 (11)	0.0359 (11)	−0.0001 (10)	0.0015 (9)	−0.0044 (9)
C5	0.0412 (11)	0.0322 (10)	0.0388 (11)	−0.0008 (9)	0.0021 (9)	0.0019 (8)
C1	0.0325 (10)	0.0340 (10)	0.0303 (10)	0.0009 (9)	0.0002 (8)	−0.0041 (8)
C3	0.0396 (11)	0.0295 (10)	0.0321 (10)	−0.0023 (9)	−0.0019 (8)	−0.0047 (8)
C11	0.0378 (12)	0.0298 (10)	0.0353 (10)	0.0028 (9)	0.0059 (8)	0.0044 (8)
C9	0.0475 (12)	0.0319 (10)	0.0365 (10)	−0.0036 (9)	−0.0043 (9)	−0.0027 (9)
C6	0.0371 (11)	0.0338 (10)	0.0406 (11)	−0.0023 (9)	0.0011 (9)	−0.0064 (9)
C10	0.0560 (13)	0.0370 (11)	0.0431 (11)	−0.0005 (10)	−0.0036 (10)	0.0038 (9)
C12	0.0552 (13)	0.0463 (11)	0.0418 (11)	−0.0040 (10)	−0.0074 (10)	0.0104 (10)
C8	0.0565 (13)	0.0740 (15)	0.0302 (10)	−0.0093 (11)	−0.0088 (10)	0.0022 (10)

Geometric parameters (Å, º)

O3—C2	1.3549 (19)	C1—C6	1.381 (2)
O3—C9	1.4390 (19)	C3—H3A	0.940
O4—C11	1.2222 (19)	C11—C12	1.497 (2)
O2—C7	1.328 (2)	C9—C10	1.499 (2)
O2—C8	1.446 (2)	C9—H9B	0.980
C4—C3	1.387 (2)	C9—H9A	0.980
C4—C5	1.388 (2)	C6—H6A	0.940
C4—N1	1.412 (2)	C10—H10C	0.970
N1—C11	1.353 (2)	C10—H10B	0.970
N1—H1	0.870	C10—H10A	0.970
O1—C7	1.2059 (19)	C12—H12C	0.970
C2—C3	1.387 (2)	C12—H12B	0.970
C2—C1	1.404 (2)	C12—H12A	0.970
C7—C1	1.491 (2)	C8—H8C	0.970
C5—C6	1.379 (2)	C8—H8B	0.970
C5—H5A	0.940	C8—H8A	0.970
C2—O3—C9	118.78 (13)	O3—C9—H9B	110.4
C7—O2—C8	115.55 (14)	C10—C9—H9B	110.4
C3—C4—C5	120.09 (16)	O3—C9—H9A	110.4
C3—C4—N1	115.99 (15)	C10—C9—H9A	110.4
C5—C4—N1	123.92 (15)	H9B—C9—H9A	108.6
C11—N1—C4	129.12 (15)	C5—C6—C1	123.28 (17)
C11—N1—H1	115.4	C5—C6—H6A	118.4
C4—N1—H1	115.4	C1—C6—H6A	118.4
O3—C2—C3	123.09 (15)	C9—C10—H10C	109.5
O3—C2—C1	117.75 (15)	C9—C10—H10B	109.5
C3—C2—C1	119.13 (15)	H10C—C10—H10B	109.5
O1—C7—O2	123.09 (16)	C9—C10—H10A	109.5
O1—C7—C1	123.31 (17)	H10C—C10—H10A	109.5
O2—C7—C1	113.57 (16)	H10B—C10—H10A	109.5
C6—C5—C4	118.06 (17)	C11—C12—H12C	109.5
C6—C5—H5A	121.0	C11—C12—H12B	109.5
C4—C5—H5A	121.0	H12C—C12—H12B	109.5
C6—C1—C2	118.15 (15)	C11—C12—H12A	109.5
C6—C1—C7	117.00 (16)	H12C—C12—H12A	109.5
C2—C1—C7	124.82 (16)	H12B—C12—H12A	109.5
C4—C3—C2	121.21 (16)	O2—C8—H8C	109.5
C4—C3—H3A	119.4	O2—C8—H8B	109.5
C2—C3—H3A	119.4	H8C—C8—H8B	109.5
O4—C11—N1	123.24 (16)	O2—C8—H8A	109.5
O4—C11—C12	122.00 (16)	H8C—C8—H8A	109.5
N1—C11—C12	114.75 (16)	H8B—C8—H8A	109.5
O3—C9—C10	106.68 (14)
C3—C4—N1—C11	174.85 (16)	O2—C7—C1—C6	152.49 (15)
C5—C4—N1—C11	−5.2 (3)	O1—C7—C1—C2	152.61 (18)
C9—O3—C2—C3	2.9 (2)	O2—C7—C1—C2	−29.4 (2)
C9—O3—C2—C1	−175.26 (15)	C5—C4—C3—C2	1.8 (3)
C8—O2—C7—O1	−3.8 (2)	N1—C4—C3—C2	−178.29 (14)
C8—O2—C7—C1	178.28 (15)	O3—C2—C3—C4	−177.71 (15)
C3—C4—C5—C6	−1.9 (3)	C1—C2—C3—C4	0.5 (2)
N1—C4—C5—C6	178.17 (15)	C4—N1—C11—O4	0.7 (3)
O3—C2—C1—C6	175.81 (15)	C4—N1—C11—C12	179.82 (15)
C3—C2—C1—C6	−2.5 (2)	C2—O3—C9—C10	171.43 (14)
O3—C2—C1—C7	−2.3 (2)	C4—C5—C6—C1	−0.2 (3)
C3—C2—C1—C7	179.47 (16)	C2—C1—C6—C5	2.4 (3)
O1—C7—C1—C6	−25.5 (3)	C7—C1—C6—C5	−179.40 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O4	0.94	2.29	2.877 (2)	120
N1—H1···O4^i	0.87	2.00	2.8652 (18)	173
C8—H8B···O4^ii	0.97	2.56	3.505 (2)	166

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