3-[(4-Bromo-1-methyl-1H-pyrrol-2-yl­carbonyl)­amino]­propanoic acid

The title compound, C₉H₁₁BrN₂O₃, was synthesized by condensation of β-alanine methyl ester with 4-bromo-1-methyl-2-(tri­chloro­acetyl)­pyrrole at room temperature. 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: see _exptl_special_details

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.208     0.354
            Tmin and Tmax expected:      0.163     0.354
            RR =      1.278
            Please check that your absorption correction is appropriate.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               1763
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         1872
           Completeness (_total/calc)             94.18%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.75 Sigma
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.08 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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, 1997); software used to prepare material for publication: SHELXTL.

3-[(4-Bromo-1-methyl-1H-pyrrol-2-ylcarbonyl)amino]propanoic acid

Crystal data

C9H11BrN2O3	Z = 2
Mr = 275.11	F(000) = 276
Triclinic, P1	Dx = 1.717 Mg m^−3
Hall symbol: -P 1	Melting point: 443 K
a = 7.824 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.153 (4) Å	Cell parameters from 783 reflections
c = 9.227 (4) Å	θ = 2.3–27.0°
α = 102.202 (8)°	µ = 3.85 mm^−1
β = 97.123 (8)°	T = 293 K
γ = 108.950 (8)°	Block, colorless
V = 532.2 (4) Å^3	0.50 × 0.46 × 0.27 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	1763 independent reflections
Radiation source: fine-focus sealed tube	1644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.208, Tmax = 0.354	k = −9→9
2812 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 0.2132P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
1763 reflections	Δρmax = 0.84 e Å^−3
141 parameters	Δρmin = −0.62 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (4)

Special details

Experimental. Because collected data were relatively weak, especially at the end of measurement, a part of reflections was marked as unobserved by data reduction software. This affect fraction of unique reflections observed (out to θ=25.0°) which is equal to 94%.

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
O2	1.0762 (4)	0.9272 (5)	0.8435 (3)	0.0709 (10)
Br1	0.36934 (5)	0.62499 (5)	1.35506 (3)	0.0468 (2)
O1	0.3852 (3)	0.7527 (3)	0.6966 (2)	0.0405 (6)
C1	0.3551 (4)	0.6142 (4)	1.1487 (3)	0.0321 (7)
N1	0.2559 (3)	0.5322 (4)	0.9008 (3)	0.0326 (6)
N2	0.6617 (3)	0.8768 (4)	0.8562 (3)	0.0344 (6)
H2B	0.7287	0.8793	0.9385	0.041*
C5	0.4831 (4)	0.7723 (4)	0.8200 (3)	0.0279 (6)
C2	0.4746 (4)	0.7383 (4)	1.0893 (3)	0.0314 (6)
H2A	0.5776	0.8382	1.1437	0.038*
O3	1.0704 (4)	0.7906 (4)	0.6088 (3)	0.0542 (7)
C3	0.4107 (4)	0.6847 (4)	0.9344 (3)	0.0283 (6)
C8	1.0042 (4)	0.8738 (4)	0.7121 (3)	0.0349 (7)
C4	0.2215 (4)	0.4878 (4)	1.0312 (4)	0.0352 (7)
H4A	0.1249	0.3894	1.0391	0.042*
C7	0.8303 (4)	0.8943 (5)	0.6460 (4)	0.0368 (7)
H7A	0.7404	0.7759	0.5929	0.044*
H7B	0.8564	0.9626	0.5719	0.044*
C6	0.7458 (5)	0.9863 (4)	0.7605 (4)	0.0381 (7)
H6A	0.8411	1.0964	0.8243	0.046*
H6B	0.6527	1.0194	0.7071	0.046*
C9	0.1530 (5)	0.4157 (5)	0.7498 (4)	0.0482 (9)
H9A	0.0502	0.3183	0.7600	0.072*
H9B	0.2330	0.3681	0.6983	0.072*
H9C	0.1086	0.4844	0.6924	0.072*
H1	1.162 (6)	0.790 (6)	0.651 (5)	0.050 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0441 (16)	0.119 (3)	0.0357 (14)	0.0323 (17)	−0.0027 (12)	−0.0063 (15)
Br1	0.0443 (3)	0.0675 (3)	0.0336 (3)	0.0199 (2)	0.01186 (16)	0.02193 (18)
O1	0.0279 (11)	0.0626 (15)	0.0297 (11)	0.0144 (11)	0.0049 (9)	0.0133 (10)
C1	0.0301 (16)	0.0402 (17)	0.0307 (15)	0.0162 (13)	0.0101 (12)	0.0115 (13)
N1	0.0236 (13)	0.0372 (14)	0.0309 (14)	0.0057 (11)	0.0055 (10)	0.0048 (11)
N2	0.0225 (13)	0.0437 (15)	0.0339 (13)	0.0065 (11)	0.0065 (10)	0.0122 (11)
C5	0.0219 (14)	0.0337 (16)	0.0276 (14)	0.0108 (12)	0.0076 (11)	0.0049 (12)
C2	0.0249 (15)	0.0382 (17)	0.0289 (15)	0.0102 (12)	0.0065 (11)	0.0062 (12)
O3	0.0430 (15)	0.088 (2)	0.0356 (13)	0.0387 (15)	0.0028 (11)	0.0031 (13)
C3	0.0165 (13)	0.0348 (16)	0.0303 (15)	0.0069 (12)	0.0049 (11)	0.0057 (12)
C8	0.0246 (15)	0.0428 (18)	0.0301 (16)	0.0042 (13)	0.0054 (12)	0.0077 (13)
C4	0.0264 (15)	0.0393 (17)	0.0394 (17)	0.0080 (13)	0.0111 (12)	0.0131 (14)
C7	0.0308 (16)	0.0454 (19)	0.0351 (16)	0.0121 (14)	0.0106 (13)	0.0133 (14)
C6	0.0323 (17)	0.0363 (17)	0.0470 (19)	0.0085 (13)	0.0174 (14)	0.0148 (14)
C9	0.0372 (19)	0.047 (2)	0.0369 (18)	−0.0029 (16)	−0.0023 (14)	−0.0019 (15)

Geometric parameters (Å, º)

O2—C8	1.194 (4)	C2—H2A	0.9300
Br1—C1	1.875 (3)	O3—C8	1.309 (4)
O1—C5	1.239 (4)	O3—H1	0.77 (5)
C1—C4	1.370 (4)	C8—C7	1.496 (4)
C1—C2	1.395 (5)	C4—H4A	0.9300
N1—C4	1.361 (4)	C7—C6	1.509 (5)
N1—C3	1.369 (4)	C7—H7A	0.9700
N1—C9	1.469 (4)	C7—H7B	0.9700
N2—C5	1.334 (4)	C6—H6A	0.9700
N2—C6	1.451 (4)	C6—H6B	0.9700
N2—H2B	0.8600	C9—H9A	0.9600
C5—C3	1.466 (4)	C9—H9B	0.9600
C2—C3	1.378 (4)	C9—H9C	0.9600
C4—C1—C2	108.4 (3)	N1—C4—C1	107.6 (3)
C4—C1—Br1	125.9 (3)	N1—C4—H4A	126.2
C2—C1—Br1	125.6 (2)	C1—C4—H4A	126.2
C4—N1—C3	109.3 (3)	C8—C7—C6	114.5 (3)
C4—N1—C9	122.8 (3)	C8—C7—H7A	108.6
C3—N1—C9	127.4 (3)	C6—C7—H7A	108.6
C5—N2—C6	121.8 (3)	C8—C7—H7B	108.6
C5—N2—H2B	119.1	C6—C7—H7B	108.6
C6—N2—H2B	119.1	H7A—C7—H7B	107.6
O1—C5—N2	121.2 (3)	N2—C6—C7	113.8 (3)
O1—C5—C3	122.5 (3)	N2—C6—H6A	108.8
N2—C5—C3	116.3 (3)	C7—C6—H6A	108.8
C3—C2—C1	106.9 (3)	N2—C6—H6B	108.8
C3—C2—H2A	126.6	C7—C6—H6B	108.8
C1—C2—H2A	126.6	H6A—C6—H6B	107.7
C8—O3—H1	106 (3)	N1—C9—H9A	109.5
N1—C3—C2	107.9 (3)	N1—C9—H9B	109.5
N1—C3—C5	123.4 (3)	H9A—C9—H9B	109.5
C2—C3—C5	128.7 (3)	N1—C9—H9C	109.5
O2—C8—O3	123.3 (3)	H9A—C9—H9C	109.5
O2—C8—C7	124.5 (3)	H9B—C9—H9C	109.5
O3—C8—C7	112.2 (3)
C6—N2—C5—O1	6.2 (5)	N2—C5—C3—N1	−157.5 (3)
C6—N2—C5—C3	−173.2 (3)	O1—C5—C3—C2	−154.1 (3)
C4—C1—C2—C3	0.0 (4)	N2—C5—C3—C2	25.4 (5)
Br1—C1—C2—C3	−177.4 (2)	C3—N1—C4—C1	0.5 (4)
C4—N1—C3—C2	−0.5 (4)	C9—N1—C4—C1	172.9 (3)
C9—N1—C3—C2	−172.4 (3)	C2—C1—C4—N1	−0.3 (4)
C4—N1—C3—C5	−178.1 (3)	Br1—C1—C4—N1	177.1 (2)
C9—N1—C3—C5	9.9 (5)	O2—C8—C7—C6	−1.4 (5)
C1—C2—C3—N1	0.3 (3)	O3—C8—C7—C6	178.9 (3)
C1—C2—C3—C5	177.7 (3)	C5—N2—C6—C7	−92.2 (4)
O1—C5—C3—N1	23.0 (5)	C8—C7—C6—N2	−71.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1^i	0.77 (5)	1.88 (5)	2.632 (3)	163 (5)
N2—H2B···O2^ii	0.86	2.28	3.005 (3)	142

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