Ethyl 2-acetyl-3-anilinobutanoate

The title compound, C₁₄H₁₉NO₃, adopts an extended conformation and forms hydrogen-bonded dimers through inter­molecular N—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.135
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.12 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: ... # Comment Author's Contributions: # Comment Group-I: Planning of Experiment/Guidance: V.V. Synthesis/Crystallization/Diagram preparation etc.: S.P. & S.S.

 Group-II:
 Data-collection/Structure Solution/Refinement etc.: T.V. & T.N.
 Report writing//Analysis/guidance: R.S.R
 # Comment


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Ethyl 2-acetyl-3-anilinobutanoate

Crystal data

C14H19NO3	Z = 2
Mr = 249.30	F(000) = 268
Triclinic, P1	Dx = 1.185 Mg m^−3
Hall symbol: -P 1	Melting point: 367 K
a = 8.045 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.390 (2) Å	Cell parameters from 766 reflections
c = 10.419 (3) Å	θ = 5–25°
α = 72.77 (1)°	µ = 0.08 mm^−1
β = 77.68 (1)°	T = 295 K
γ = 69.49 (1)°	Plate, colourless
V = 698.8 (3) Å^3	0.23 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2734 independent reflections
Radiation source: fine-focus sealed tube	1672 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.931, Tmax = 0.998	k = −11→11
7266 measured reflections	l = −12→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.1336P] where P = (Fo^2 + 2Fc^2)/3
2734 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.13 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.

===========================================================================

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = 0.97493(0.00022) m2 = 0.11243(0.00081) m3 = -0.19200(0.00116) D = 2.74426(0.00405) Atom d s d/s (d/s)**2 C1 * 0.0267 0.0023 11.425 130.528 C2 * 0.0140 0.0029 4.840 23.428 C3 * -0.0054 0.0032 - 1.674 2.803 C4 * -0.0218 0.0030 - 7.235 52.345 C5 * -0.0087 0.0028 - 3.041 9.250 C6 * 0.0165 0.0026 6.401 40.978 N7 * -0.0236 0.0022 - 10.918 119.201 C8 0.4148 0.0023 176.625 31196.385 ============ Sum((d/s)**2) for starred atoms 378.532 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity

Plane 2 m1 = 0.23650(0.00113) m2 = -0.93511(0.00050) m3 = -0.26389(0.00132) D = -5.12636(0.00269) Atom d s d/s (d/s)**2 C10 * -0.0009 0.0020 - 0.424 0.180 C11 * 0.0031 0.0021 1.483 2.199 C13 * -0.0015 0.0026 - 0.562 0.316 O12 * -0.0008 0.0017 - 0.471 0.222 C8 1.1122 0.0021 523.038 273568.656 C14 - 1.3685 0.0022 - 620.629 385180.250 ============ Sum((d/s)**2) for starred atoms 2.916 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity

Plane 3 m1 = 0.98424(0.00024) m2 = -0.04785(0.00076) m3 = -0.17026(0.00130) D = 1.64917(0.00784) Atom d s d/s (d/s)**2 O15 * -0.0080 0.0023 - 3.436 11.808 O16 * 0.0249 0.0017 14.479 209.655 C10 * -0.0234 0.0022 - 10.384 107.824 C14 * 0.0130 0.0024 5.325 28.361 C17 * -0.0056 0.0031 - 1.790 3.204 C18 * -0.0472 0.0035 - 13.654 186.444 C8 0.8844 0.0024 375.986 141365.516 ============ Sum((d/s)**2) for starred atoms 547.296 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 79.86 (0.08) 100.14 (0.08) 1 3 9.29 (0.06) 170.71 (0.06) 2 3 71.19 (0.08) 108.81 (0.08)

=================================================================

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
C1	0.2549 (3)	0.1532 (2)	0.2340 (2)	0.0453 (5)
C2	0.2776 (3)	0.0901 (3)	0.3693 (2)	0.0650 (7)
H2	0.2394	0.1549	0.4291	0.078*
C3	0.3568 (4)	−0.0686 (3)	0.4157 (3)	0.0794 (8)
H3	0.3721	−0.1095	0.5068	0.095*
C4	0.4133 (4)	−0.1669 (3)	0.3306 (3)	0.0731 (7)
H4	0.4657	−0.2739	0.3632	0.088*
C5	0.3915 (3)	−0.1056 (3)	0.1968 (3)	0.0673 (7)
H5	0.4299	−0.1716	0.1380	0.081*
C6	0.3139 (3)	0.0518 (3)	0.1480 (2)	0.0558 (6)
H6	0.3005	0.0914	0.0564	0.067*
N7	0.1679 (2)	0.3108 (2)	0.1814 (2)	0.0512 (5)
H7	0.190 (3)	0.339 (3)	0.094 (2)	0.064 (7)*
C8	0.1536 (3)	0.4335 (2)	0.2461 (2)	0.0484 (5)
H8	0.1284	0.3952	0.3442	0.058*
C9	0.3231 (3)	0.4806 (3)	0.2169 (3)	0.0828 (8)
H9A	0.3473	0.5217	0.1212	0.124*
H9B	0.4215	0.3906	0.2473	0.124*
H9C	0.3073	0.5594	0.2636	0.124*
C10	−0.0076 (3)	0.5712 (2)	0.19617 (19)	0.0428 (5)
H10	0.0207	0.6135	0.0990	0.051*
C11	−0.1712 (3)	0.5166 (2)	0.2170 (2)	0.0484 (5)
O12	−0.2581 (2)	0.54941 (19)	0.12440 (16)	0.0673 (5)
C13	−0.2222 (3)	0.4233 (3)	0.3543 (2)	0.0650 (7)
H13A	−0.1404	0.3188	0.3689	0.097*
H13B	−0.3413	0.4195	0.3598	0.097*
H13C	−0.2177	0.4718	0.4221	0.097*
C14	−0.0527 (3)	0.7012 (2)	0.2677 (2)	0.0483 (5)
O15	−0.0542 (3)	0.68132 (18)	0.38684 (16)	0.0845 (6)
O16	−0.0967 (2)	0.84055 (16)	0.18327 (14)	0.0566 (4)
C17	−0.1516 (4)	0.9758 (2)	0.2422 (2)	0.0694 (7)
H17A	−0.0539	0.9761	0.2829	0.083*
H17B	−0.2523	0.9714	0.3120	0.083*
C18	−0.2021 (4)	1.1180 (3)	0.1331 (3)	0.0849 (9)
H18A	−0.3004	1.1176	0.0949	0.127*
H18B	−0.1020	1.1205	0.0641	0.127*
H18C	−0.2368	1.2087	0.1691	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0493 (12)	0.0419 (12)	0.0455 (12)	−0.0126 (9)	−0.0045 (9)	−0.0143 (10)
C2	0.0967 (18)	0.0458 (14)	0.0463 (14)	−0.0082 (12)	−0.0120 (12)	−0.0164 (11)
C3	0.123 (2)	0.0516 (16)	0.0504 (14)	−0.0099 (15)	−0.0177 (15)	−0.0078 (12)
C4	0.096 (2)	0.0399 (13)	0.0704 (18)	−0.0071 (13)	−0.0074 (15)	−0.0137 (13)
C5	0.0856 (18)	0.0489 (15)	0.0675 (17)	−0.0146 (13)	−0.0003 (14)	−0.0279 (13)
C6	0.0708 (15)	0.0508 (14)	0.0466 (13)	−0.0155 (11)	−0.0023 (11)	−0.0200 (11)
N7	0.0687 (12)	0.0428 (11)	0.0415 (11)	−0.0095 (9)	−0.0120 (9)	−0.0148 (9)
C8	0.0558 (13)	0.0426 (12)	0.0510 (13)	−0.0121 (10)	−0.0128 (10)	−0.0170 (10)
C9	0.0627 (16)	0.0782 (19)	0.121 (2)	−0.0217 (14)	−0.0190 (16)	−0.0374 (17)
C10	0.0570 (13)	0.0383 (11)	0.0344 (11)	−0.0150 (10)	−0.0069 (9)	−0.0093 (9)
C11	0.0567 (13)	0.0416 (12)	0.0449 (13)	−0.0067 (10)	−0.0100 (10)	−0.0150 (10)
O12	0.0725 (11)	0.0791 (12)	0.0543 (10)	−0.0241 (9)	−0.0219 (8)	−0.0113 (9)
C13	0.0657 (15)	0.0756 (17)	0.0543 (14)	−0.0325 (13)	−0.0050 (12)	−0.0054 (12)
C14	0.0610 (14)	0.0415 (13)	0.0429 (13)	−0.0150 (10)	−0.0082 (10)	−0.0109 (10)
O15	0.1535 (18)	0.0537 (11)	0.0433 (10)	−0.0160 (10)	−0.0273 (10)	−0.0159 (8)
O16	0.0862 (11)	0.0358 (8)	0.0457 (9)	−0.0158 (7)	−0.0040 (7)	−0.0132 (7)
C17	0.103 (2)	0.0437 (14)	0.0643 (16)	−0.0204 (13)	−0.0041 (14)	−0.0244 (12)
C18	0.119 (2)	0.0469 (15)	0.082 (2)	−0.0144 (15)	−0.0090 (17)	−0.0211 (14)

Geometric parameters (Å, º)

C1—C2	1.382 (3)	C9—H9C	0.9600
C1—N7	1.392 (3)	C10—C14	1.513 (3)
C1—C6	1.394 (3)	C10—C11	1.526 (3)
C2—C3	1.378 (3)	C10—H10	0.9800
C2—H2	0.9300	C11—O12	1.215 (2)
C3—C4	1.365 (3)	C11—C13	1.497 (3)
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.365 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.370 (3)	C14—O15	1.198 (2)
C5—H5	0.9300	C14—O16	1.318 (2)
C6—H6	0.9300	O16—C17	1.463 (2)
N7—C8	1.459 (3)	C17—C18	1.469 (3)
N7—H7	0.86 (2)	C17—H17A	0.9700
C8—C9	1.521 (3)	C17—H17B	0.9700
C8—C10	1.529 (3)	C18—H18A	0.9600
C8—H8	0.9800	C18—H18B	0.9600
C9—H9A	0.9600	C18—H18C	0.9600
C9—H9B	0.9600
C2—C1—N7	123.26 (19)	H9B—C9—H9C	109.5
C2—C1—C6	118.0 (2)	C14—C10—C11	108.81 (16)
N7—C1—C6	118.65 (19)	C14—C10—C8	112.20 (16)
C3—C2—C1	120.1 (2)	C11—C10—C8	110.47 (16)
C3—C2—H2	119.9	C14—C10—H10	108.4
C1—C2—H2	119.9	C11—C10—H10	108.4
C4—C3—C2	121.4 (2)	C8—C10—H10	108.4
C4—C3—H3	119.3	O12—C11—C13	121.2 (2)
C2—C3—H3	119.3	O12—C11—C10	120.50 (19)
C3—C4—C5	118.9 (2)	C13—C11—C10	118.33 (18)
C3—C4—H4	120.5	C11—C13—H13A	109.5
C5—C4—H4	120.5	C11—C13—H13B	109.5
C4—C5—C6	120.9 (2)	H13A—C13—H13B	109.5
C4—C5—H5	119.5	C11—C13—H13C	109.5
C6—C5—H5	119.5	H13A—C13—H13C	109.5
C5—C6—C1	120.7 (2)	H13B—C13—H13C	109.5
C5—C6—H6	119.7	O15—C14—O16	123.70 (19)
C1—C6—H6	119.7	O15—C14—C10	124.63 (19)
C1—N7—C8	122.62 (18)	O16—C14—C10	111.64 (17)
C1—N7—H7	112.9 (15)	C14—O16—C17	116.55 (16)
C8—N7—H7	112.1 (15)	O16—C17—C18	107.84 (19)
N7—C8—C9	113.05 (19)	O16—C17—H17A	110.1
N7—C8—C10	106.12 (16)	C18—C17—H17A	110.1
C9—C8—C10	112.05 (18)	O16—C17—H17B	110.1
N7—C8—H8	108.5	C18—C17—H17B	110.1
C9—C8—H8	108.5	H17A—C17—H17B	108.5
C10—C8—H8	108.5	C17—C18—H18A	109.5
C8—C9—H9A	109.5	C17—C18—H18B	109.5
C8—C9—H9B	109.5	H18A—C18—H18B	109.5
H9A—C9—H9B	109.5	C17—C18—H18C	109.5
C8—C9—H9C	109.5	H18A—C18—H18C	109.5
H9A—C9—H9C	109.5	H18B—C18—H18C	109.5
N7—C1—C2—C3	176.6 (2)	N7—C8—C10—C11	51.7 (2)
C6—C1—C2—C3	0.1 (4)	C9—C8—C10—C11	175.48 (18)
C1—C2—C3—C4	−0.5 (4)	C14—C10—C11—O12	107.2 (2)
C2—C3—C4—C5	0.5 (4)	C8—C10—C11—O12	−129.2 (2)
C3—C4—C5—C6	−0.2 (4)	C14—C10—C11—C13	−72.2 (2)
C4—C5—C6—C1	−0.1 (4)	C8—C10—C11—C13	51.4 (2)
C2—C1—C6—C5	0.2 (3)	C11—C10—C14—O15	79.7 (3)
N7—C1—C6—C5	−176.4 (2)	C8—C10—C14—O15	−42.8 (3)
C2—C1—N7—C8	24.3 (3)	C11—C10—C14—O16	−98.1 (2)
C6—C1—N7—C8	−159.3 (2)	C8—C10—C14—O16	139.35 (18)
C1—N7—C8—C9	79.4 (3)	O15—C14—O16—C17	−0.7 (3)
C1—N7—C8—C10	−157.36 (18)	C10—C14—O16—C17	177.13 (18)
N7—C8—C10—C14	173.25 (17)	C14—O16—C17—C18	−177.5 (2)
C9—C8—C10—C14	−62.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O12^i	0.87 (2)	2.24 (2)	3.099 (3)	169 (2)

Symmetry code: (i) −x, −y+1, −z.