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The title compound, C11H13NO4, was obtained by reaction of methyl 2-amino­benzoate and 2-methoxy­acetyl chloride. The two side chains lie in the same plane as the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026468/sg2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026468/sg2046Isup2.hkl
Contains datablock I

CCDC reference: 618329

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.170
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

Methyl 2-(methoxyacetylamino)benzoate top
Crystal data top
C11H13NO4F(000) = 236
Mr = 223.22Dx = 1.334 Mg m3
Triclinic, P1Melting point: 72 K
a = 7.149 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.649 (5) ÅCell parameters from 799 reflections
c = 9.973 (5) Åθ = 2.6–25.0°
α = 67.462 (5)°µ = 0.10 mm1
β = 89.982 (7)°T = 293 K
γ = 78.350 (7)°Prism, colorless
V = 555.8 (5) Å30.24 × 0.16 × 0.12 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1941 independent reflections
Radiation source: fine-focus sealed tube1166 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.975, Tmax = 0.988k = 810
3000 measured reflectionsl = 911
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0937P)2]
where P = (Fo2 + 2Fc2)/3
1941 reflections(Δ/σ)max = 0.001
147 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. 1H NMR (300 MHz, CDCl3): δ 3.58 (s, 3H, CH3), 3.95 (s, 3H, CH3),4.07 (s, 2H, CH2), 7.13 (dd, 1H, PhH), 7.56 (dd, 1H, PhH), 8.07 (d, 1H, PhH), 8.79 (d, 1H, PhH).

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
xyzUiso*/Ueq
O10.1811 (3)0.7451 (2)0.39950 (17)0.0614 (6)
O20.1902 (3)0.7370 (2)0.62479 (19)0.0783 (7)
O30.3300 (3)0.1892 (2)1.0586 (2)0.0845 (7)
O40.2159 (4)0.6334 (3)0.9812 (2)0.0961 (8)
N10.2723 (3)0.4291 (2)0.8447 (2)0.0540 (6)
H10.24580.53930.81250.065*
C10.1338 (4)0.9299 (3)0.3440 (3)0.0703 (8)
H1A0.00570.96810.36490.106*
H1B0.14230.97580.24050.106*
H1C0.22200.96890.38960.106*
C20.2070 (4)0.6613 (3)0.5435 (3)0.0519 (6)
C30.2573 (3)0.4739 (3)0.5884 (2)0.0465 (6)
C40.2764 (4)0.4030 (3)0.4831 (3)0.0597 (7)
H40.25580.47610.38520.072*
C50.3242 (4)0.2306 (4)0.5192 (3)0.0704 (8)
H50.33550.18730.44670.085*
C60.3559 (4)0.1206 (3)0.6639 (3)0.0707 (9)
H60.38740.00270.68890.085*
C70.3411 (4)0.1838 (3)0.7714 (3)0.0629 (8)
H70.36530.10810.86850.075*
C80.2906 (3)0.3594 (3)0.7374 (3)0.0482 (6)
C90.2910 (4)0.3449 (3)0.9933 (3)0.0572 (7)
C100.2589 (4)0.4614 (3)1.0754 (3)0.0658 (8)
H10A0.15430.43691.13660.079*
H10B0.37330.43881.13820.079*
C110.1849 (5)0.7484 (4)1.0504 (3)0.0811 (9)
H11A0.07420.73441.10460.122*
H11B0.16440.86370.97870.122*
H11C0.29490.72621.11560.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0943 (14)0.0502 (11)0.0356 (10)0.0117 (9)0.0089 (8)0.0143 (8)
O20.1383 (19)0.0508 (11)0.0413 (11)0.0020 (11)0.0043 (11)0.0223 (9)
O30.1240 (18)0.0607 (13)0.0493 (11)0.0082 (12)0.0118 (11)0.0064 (10)
O40.180 (2)0.0679 (13)0.0389 (11)0.0123 (13)0.0090 (12)0.0269 (10)
N10.0743 (15)0.0470 (12)0.0356 (11)0.0090 (10)0.0051 (10)0.0127 (9)
C10.100 (2)0.0503 (17)0.0497 (16)0.0127 (15)0.0058 (15)0.0093 (13)
C20.0614 (16)0.0534 (15)0.0392 (14)0.0091 (12)0.0059 (11)0.0181 (12)
C30.0529 (15)0.0467 (14)0.0427 (13)0.0105 (11)0.0076 (11)0.0206 (11)
C40.0759 (19)0.0593 (17)0.0500 (16)0.0106 (14)0.0067 (13)0.0299 (13)
C50.091 (2)0.0651 (18)0.069 (2)0.0139 (15)0.0123 (16)0.0433 (16)
C60.084 (2)0.0478 (16)0.082 (2)0.0073 (14)0.0078 (17)0.0305 (15)
C70.079 (2)0.0457 (16)0.0561 (17)0.0072 (13)0.0042 (14)0.0148 (13)
C80.0530 (15)0.0487 (14)0.0433 (14)0.0092 (11)0.0072 (11)0.0194 (11)
C90.0629 (16)0.0606 (17)0.0368 (14)0.0107 (13)0.0051 (12)0.0082 (12)
C100.084 (2)0.073 (2)0.0350 (14)0.0144 (15)0.0086 (13)0.0160 (13)
C110.111 (3)0.078 (2)0.0635 (19)0.0181 (18)0.0120 (17)0.0393 (16)
Geometric parameters (Å, º) top
O1—C21.331 (3)C4—C51.361 (3)
O1—C11.442 (3)C4—H40.9300
O2—C21.214 (3)C5—C61.378 (4)
O3—C91.221 (3)C5—H50.9300
O4—C101.391 (3)C6—C71.374 (4)
O4—C111.398 (4)C6—H60.9300
N1—C91.371 (3)C7—C81.391 (3)
N1—C81.410 (3)C7—H70.9300
N1—H10.8600C9—C101.509 (4)
C1—H1A0.9600C10—H10A0.9700
C1—H1B0.9600C10—H10B0.9700
C1—H1C0.9600C11—H11A0.9600
C2—C31.472 (3)C11—H11B0.9600
C3—C41.399 (3)C11—H11C0.9600
C3—C81.422 (3)
C2—O1—C1117.1 (2)C7—C6—H6119.8
C10—O4—C11114.5 (2)C5—C6—H6119.8
C9—N1—C8128.7 (2)C6—C7—C8121.0 (2)
C9—N1—H1115.7C6—C7—H7119.5
C8—N1—H1115.7C8—C7—H7119.5
O1—C1—H1A109.5C7—C8—N1122.7 (2)
O1—C1—H1B109.5C7—C8—C3118.9 (2)
H1A—C1—H1B109.5N1—C8—C3118.4 (2)
O1—C1—H1C109.5O3—C9—N1124.9 (3)
H1A—C1—H1C109.5O3—C9—C10120.7 (2)
H1B—C1—H1C109.5N1—C9—C10114.4 (2)
O2—C2—O1121.5 (2)O4—C10—C9111.6 (2)
O2—C2—C3125.8 (2)O4—C10—H10A109.3
O1—C2—C3112.7 (2)C9—C10—H10A109.3
C4—C3—C8117.8 (2)O4—C10—H10B109.3
C4—C3—C2120.1 (2)C9—C10—H10B109.3
C8—C3—C2122.1 (2)H10A—C10—H10B108.0
C5—C4—C3122.2 (3)O4—C11—H11A109.5
C5—C4—H4118.9O4—C11—H11B109.5
C3—C4—H4118.9H11A—C11—H11B109.5
C4—C5—C6119.6 (3)O4—C11—H11C109.5
C4—C5—H5120.2H11A—C11—H11C109.5
C6—C5—H5120.2H11B—C11—H11C109.5
C7—C6—C5120.5 (3)
C1—O1—C2—O20.6 (4)C6—C7—C8—C31.1 (4)
C1—O1—C2—C3179.2 (2)C9—N1—C8—C72.8 (4)
O2—C2—C3—C4178.5 (3)C9—N1—C8—C3177.6 (2)
O1—C2—C3—C41.2 (3)C4—C3—C8—C70.3 (4)
O2—C2—C3—C80.6 (4)C2—C3—C8—C7178.8 (2)
O1—C2—C3—C8179.7 (2)C4—C3—C8—N1179.9 (2)
C8—C3—C4—C50.3 (4)C2—C3—C8—N10.7 (3)
C2—C3—C4—C5179.5 (2)C8—N1—C9—O30.7 (4)
C3—C4—C5—C60.2 (4)C8—N1—C9—C10179.2 (2)
C4—C5—C6—C70.6 (4)C11—O4—C10—C9179.8 (3)
C5—C6—C7—C81.2 (5)O3—C9—C10—O4179.9 (3)
C6—C7—C8—N1179.4 (3)N1—C9—C10—O40.1 (3)
 

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