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The title compound, C9H12N2O3, was synthesized by condensation of β-alanine methyl ester with 1-methyl-2-(trichloro­acet­yl)pyrrole at room temperature, followed by saponification and acidification. In the crystal structure, inter­molecular N—H...O and O—H...O hydrogen-bond inter­actions link the mol­ecules into extended ribbons parallel to the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006040/sj2003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006040/sj2003Isup2.hkl
Contains datablock I

CCDC reference: 601250

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.123
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 480.70 Ang-3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
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 4 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 1997); software used to prepare material for publication: SHELXTL.

3-(1-Methyl-1H-pyrrole-2-carboxamido)propanoic acid top
Crystal data top
C9H12N2O3Z = 2
Mr = 196.21F(000) = 208
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Melting point: 406 K
a = 7.651 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.270 (3) ÅCell parameters from 1580 reflections
c = 8.551 (3) Åθ = 2.6–21.9°
α = 88.297 (5)°µ = 0.10 mm1
β = 70.119 (5)°T = 293 K
γ = 71.488 (5)°Block, colorless
V = 480.7 (3) Å30.40 × 0.35 × 0.19 mm
Data collection top
Bruker SMART area-detector
diffractometer
2047 independent reflections
Radiation source: fine-focus sealed tube1428 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 27.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.960, Tmax = 0.981k = 1010
3942 measured reflectionsl = 1010
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0659P)2 + 0.0529P]
where P = (Fo2 + 2Fc2)/3
2047 reflections(Δ/σ)max = 0.001
129 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.31802 (16)0.82740 (14)0.22651 (14)0.0479 (3)
N20.62222 (18)0.64149 (17)0.11210 (16)0.0430 (4)
H20.70290.54090.10940.052*
O30.96256 (18)0.89971 (16)0.21843 (16)0.0596 (4)
H31.07540.86090.21850.089*
C50.4379 (2)0.68288 (19)0.21799 (18)0.0373 (4)
C80.9415 (2)0.8090 (2)0.1071 (2)0.0418 (4)
C40.3866 (2)0.5488 (2)0.32086 (19)0.0404 (4)
O21.0672 (2)0.68284 (17)0.0303 (2)0.0737 (5)
N10.2338 (2)0.58500 (18)0.47127 (16)0.0467 (4)
C60.6903 (3)0.7619 (2)0.0012 (2)0.0484 (4)
H6A0.58690.82670.03950.058*
H6B0.80280.69910.09420.058*
C70.7474 (2)0.8840 (2)0.0846 (2)0.0472 (4)
H7A0.75080.98130.01880.057*
H7B0.64670.92620.19330.057*
C30.4677 (3)0.3743 (2)0.2905 (2)0.0529 (5)
H3A0.57380.31420.19770.063*
C10.2211 (3)0.4349 (3)0.5328 (2)0.0603 (5)
H10.13000.42390.63360.072*
C90.1198 (3)0.7508 (3)0.5638 (2)0.0629 (5)
H9A0.19890.82450.53850.094*
H9B0.07900.73720.68120.094*
H9C0.00590.80060.53280.094*
C20.3612 (3)0.3033 (3)0.4251 (3)0.0651 (6)
H2A0.38280.18730.43810.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0337 (6)0.0449 (7)0.0591 (7)0.0087 (5)0.0130 (5)0.0086 (5)
N20.0329 (7)0.0434 (7)0.0464 (8)0.0096 (6)0.0088 (6)0.0041 (6)
O30.0389 (7)0.0603 (8)0.0731 (9)0.0067 (6)0.0190 (6)0.0115 (7)
C50.0325 (8)0.0414 (9)0.0387 (8)0.0116 (7)0.0132 (6)0.0005 (6)
C80.0338 (9)0.0372 (8)0.0461 (9)0.0117 (7)0.0041 (7)0.0067 (7)
C40.0349 (8)0.0465 (9)0.0424 (9)0.0160 (7)0.0143 (7)0.0029 (7)
O20.0445 (8)0.0629 (9)0.0956 (11)0.0053 (7)0.0207 (7)0.0261 (8)
N10.0420 (8)0.0558 (9)0.0437 (8)0.0213 (7)0.0118 (6)0.0079 (6)
C60.0408 (9)0.0633 (11)0.0399 (9)0.0197 (8)0.0105 (7)0.0112 (8)
C70.0366 (9)0.0440 (9)0.0566 (10)0.0121 (7)0.0127 (8)0.0118 (8)
C30.0523 (11)0.0453 (10)0.0621 (11)0.0172 (8)0.0200 (9)0.0041 (8)
C10.0642 (13)0.0735 (13)0.0574 (11)0.0387 (11)0.0252 (10)0.0258 (10)
C90.0565 (12)0.0699 (13)0.0477 (10)0.0188 (10)0.0013 (9)0.0033 (9)
C20.0744 (14)0.0533 (11)0.0834 (15)0.0331 (11)0.0370 (12)0.0235 (11)
Geometric parameters (Å, º) top
O1—C51.2404 (18)C6—C71.501 (2)
N2—C51.3303 (19)C6—H6A0.9700
N2—C61.449 (2)C6—H6B0.9700
N2—H20.8600C7—H7A0.9700
O3—C81.311 (2)C7—H7B0.9700
O3—H30.8200C3—C21.400 (3)
C5—C41.463 (2)C3—H3A0.9300
C8—O21.1912 (19)C1—C21.352 (3)
C8—C71.493 (2)C1—H10.9300
C4—C31.371 (2)C9—H9A0.9600
C4—N11.374 (2)C9—H9B0.9600
N1—C11.353 (2)C9—H9C0.9600
N1—C91.450 (2)C2—H2A0.9300
C5—N2—C6121.56 (14)C8—C7—C6114.56 (15)
C5—N2—H2119.2C8—C7—H7A108.6
C6—N2—H2119.2C6—C7—H7A108.6
C8—O3—H3109.5C8—C7—H7B108.6
O1—C5—N2120.98 (14)C6—C7—H7B108.6
O1—C5—C4122.78 (14)H7A—C7—H7B107.6
N2—C5—C4116.24 (14)C4—C3—C2107.32 (17)
O2—C8—O3122.79 (16)C4—C3—H3A126.3
O2—C8—C7124.42 (17)C2—C3—H3A126.3
O3—C8—C7112.77 (14)C2—C1—N1109.58 (17)
C3—C4—N1107.91 (14)C2—C1—H1125.2
C3—C4—C5129.69 (15)N1—C1—H1125.2
N1—C4—C5122.37 (14)N1—C9—H9A109.5
C1—N1—C4108.03 (15)N1—C9—H9B109.5
C1—N1—C9123.77 (16)H9A—C9—H9B109.5
C4—N1—C9127.71 (14)N1—C9—H9C109.5
N2—C6—C7112.74 (14)H9A—C9—H9C109.5
N2—C6—H6A109.0H9B—C9—H9C109.5
C7—C6—H6A109.0C1—C2—C3107.16 (17)
N2—C6—H6B109.0C1—C2—H2A126.4
C7—C6—H6B109.0C3—C2—H2A126.4
H6A—C6—H6B107.8
C6—N2—C5—O10.7 (2)C5—N2—C6—C782.65 (18)
C6—N2—C5—C4178.86 (13)O2—C8—C7—C619.6 (2)
O1—C5—C4—C3153.60 (17)O3—C8—C7—C6162.11 (14)
N2—C5—C4—C326.0 (2)N2—C6—C7—C876.33 (18)
O1—C5—C4—N124.3 (2)N1—C4—C3—C20.24 (19)
N2—C5—C4—N1156.13 (14)C5—C4—C3—C2177.88 (17)
C3—C4—N1—C10.06 (18)C4—N1—C1—C20.4 (2)
C5—C4—N1—C1178.35 (15)C9—N1—C1—C2172.85 (17)
C3—C4—N1—C9172.18 (17)N1—C1—C2—C30.5 (2)
C5—C4—N1—C99.5 (3)C4—C3—C2—C10.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.821.812.6176 (18)167
N2—H2···O2ii0.862.142.916 (2)150
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z.
 

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