3-(5-Bromo-2-hydroxy­benzyl­ammonio)propanoate

Yin, X.-J.; Cai, J.-H.; Ng, S.W.

doi:10.1107/S1600536806045636

3-(5-Bromo-2-hydroxybenzylammonio)propanoate

The title compound, C₁₀H₁₂BrNO₃, exists as a zwitterion in the solid state; the delocalized -CO₂ unit carries the negative charge and the secondary N atom carries the positive charge.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045636/bi2086sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045636/bi2086Isup2.hkl Contains datablock I

CCDC reference: 629437

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.035
wR factor = 0.082
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       5.97
            Cell volume su given      =       8.00
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT163_ALERT_4_C Missing or Zero su (esd) on z-coordinate for ...        BR1
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1   -H1O     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1   -H1O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N1   -H2N     1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.10
           From the CIF: _reflns_number_total               2177
           Count of symmetry unique reflns         1349
           Completeness (_total/calc)            161.38%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       828
           Fraction of Friedel pairs measured     0.614
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

3-(5-Bromo-2-hydroxybenzylammonio)propanoate top

Crystal data top

C₁₀H₁₂BrNO₃	F(000) = 552
M_r = 274.12	D_x = 1.643 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 747 reflections
a = 13.971 (4) Å	θ = 2.9–24.2°
b = 14.280 (4) Å	µ = 3.70 mm⁻¹
c = 5.553 (2) Å	T = 293 K
V = 1107.9 (8) Å³	Prism, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker APEX-II CCD diffractometer	2177 independent reflections
Radiation source: fine-focus sealed tube	1687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 27.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→17
T_min = 0.366, T_max = 0.477	k = −18→18
5103 measured reflections	l = −7→6

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max = 0.001
2177 reflections	Δρ_max = 0.54 e Å⁻³
147 parameters	Δρ_min = −0.40 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 825 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (1)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.31549 (3)	0.73643 (3)	0.5000	0.0595 (2)
O1	0.6678 (2)	0.6720 (2)	1.1067 (6)	0.059 (1)
O2	0.5820 (2)	0.9761 (2)	0.6379 (6)	0.048 (1)
O3	0.7069 (2)	1.0457 (2)	0.4733 (7)	0.054 (1)
N1	0.5958 (2)	0.9155 (2)	1.1230 (6)	0.037 (1)
C1	0.5886 (3)	0.6826 (2)	0.9718 (9)	0.042 (1)
C2	0.5659 (3)	0.6218 (3)	0.7810 (9)	0.050 (1)
C3	0.4844 (3)	0.6361 (3)	0.6440 (9)	0.052 (1)
C4	0.4259 (3)	0.7106 (3)	0.6941 (8)	0.045 (1)
C5	0.4460 (3)	0.7716 (3)	0.8837 (8)	0.042 (1)
C6	0.5282 (3)	0.7586 (2)	1.021 (1)	0.038 (1)
C7	0.5521 (3)	0.8272 (3)	1.2207 (7)	0.039 (1)
C8	0.6922 (2)	0.9026 (2)	1.018 (1)	0.041 (1)
C9	0.7237 (3)	0.9892 (3)	0.8747 (8)	0.043 (1)
C10	0.6671 (3)	1.0047 (2)	0.6459 (7)	0.037 (1)
H1o	0.698 (3)	0.622 (2)	1.07 (1)	0.09 (2)*
H1n	0.557 (2)	0.938 (2)	1.021 (5)	0.03 (1)*
H2n	0.601 (3)	0.957 (2)	1.233 (6)	0.06 (2)*
H2	0.6060	0.5715	0.7465	0.060*
H3	0.4694	0.5955	0.5187	0.063*
H5	0.4046	0.8208	0.9182	0.051*
H7a	0.4942	0.8426	1.3087	0.046*
H7b	0.5964	0.7981	1.3323	0.046*
H8a	0.6917	0.8485	0.9119	0.049*
H8b	0.7379	0.8907	1.1455	0.049*
H9a	0.7172	1.0441	0.9765	0.051*
H9b	0.7909	0.9828	0.8336	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0521 (2)	0.0723 (3)	0.0542 (3)	−0.0146 (2)	−0.0177 (3)	0.0003 (4)
O1	0.060 (2)	0.053 (2)	0.065 (2)	0.016 (2)	−0.018 (2)	−0.007 (2)
O2	0.046 (2)	0.052 (2)	0.045 (2)	−0.005 (1)	−0.010 (1)	−0.002 (1)
O3	0.060 (2)	0.062 (2)	0.040 (2)	−0.009 (1)	0.004 (2)	0.005 (2)
N1	0.044 (2)	0.034 (2)	0.032 (2)	0.004 (2)	−0.009 (2)	−0.001 (2)
C1	0.046 (2)	0.031 (2)	0.047 (3)	−0.002 (1)	−0.004 (2)	0.005 (2)
C2	0.063 (3)	0.028 (2)	0.060 (3)	0.005 (2)	−0.002 (2)	−0.010 (2)
C3	0.063 (3)	0.044 (2)	0.049 (3)	−0.012 (2)	−0.005 (2)	−0.007 (2)
C4	0.041 (2)	0.053 (2)	0.042 (2)	−0.010 (2)	−0.010 (2)	0.003 (2)
C5	0.039 (2)	0.046 (2)	0.041 (2)	−0.002 (1)	−0.003 (2)	0.003 (2)
C6	0.045 (2)	0.033 (2)	0.035 (2)	−0.006 (1)	0.000 (2)	0.003 (2)
C7	0.044 (2)	0.038 (2)	0.034 (2)	−0.003 (2)	−0.003 (2)	0.003 (2)
C8	0.041 (2)	0.039 (2)	0.042 (2)	0.003 (1)	−0.006 (2)	0.004 (2)
C9	0.038 (2)	0.047 (2)	0.043 (2)	−0.008 (2)	−0.005 (2)	0.001 (2)
C10	0.042 (2)	0.028 (2)	0.041 (2)	−0.003 (2)	−0.004 (2)	−0.005 (2)

Geometric parameters (Å, º) top

Br1—C4	1.917 (4)	C9—C10	1.513 (6)
O1—C1	1.345 (5)	O1—H1o	0.85 (1)
O2—C10	1.257 (4)	N1—H1n	0.85 (1)
O3—C10	1.254 (5)	N1—H2n	0.85 (1)
N1—C8	1.480 (5)	C2—H2	0.93
N1—C7	1.502 (5)	C3—H3	0.93
C1—C2	1.406 (6)	C5—H5	0.93
C1—C6	1.402 (5)	C7—H7a	0.97
C2—C3	1.385 (6)	C7—H7b	0.97
C3—C4	1.370 (6)	C8—H8a	0.97
C4—C5	1.395 (6)	C8—H8b	0.97
C5—C6	1.390 (6)	C9—H9a	0.97
C6—C7	1.517 (6)	C9—H9b	0.97
C8—C9	1.534 (6)

C8—N1—C7	114.1 (3)	C7—N1—H2n	111 (3)
O1—C1—C2	122.4 (3)	H1n—N1—H2n	106 (4)
O1—C1—C6	118.3 (4)	C3—C2—H2	119.7
C2—C1—C6	119.3 (4)	C1—C2—H2	119.7
C3—C2—C1	120.5 (4)	C4—C3—H3	120.2
C4—C3—C2	119.6 (4)	C2—C3—H3	120.2
C3—C4—C5	121.2 (4)	C6—C5—H5	120.1
C3—C4—Br1	121.0 (3)	C4—C5—H5	120.1
C5—C4—Br1	117.8 (3)	N1—C7—H7a	109.3
C6—C5—C4	119.8 (4)	C6—C7—H7a	109.3
C5—C6—C1	119.6 (4)	N1—C7—H7b	109.3
C5—C6—C7	119.8 (3)	C6—C7—H7b	109.3
C1—C6—C7	120.6 (4)	H7a—C7—H7b	108.0
N1—C7—C6	111.5 (3)	N1—C8—H8a	109.3
N1—C8—C9	111.4 (3)	C9—C8—H8a	109.3
C10—C9—C8	113.7 (3)	N1—C8—H8b	109.3
O3—C10—O2	123.0 (4)	C9—C8—H8b	109.3
O3—C10—C9	118.5 (3)	H8a—C8—H8b	108.0
O2—C10—C9	118.5 (4)	C10—C9—H9a	108.8
C1—O1—H1o	111 (4)	C8—C9—H9a	108.8
C8—N1—H1n	112 (3)	C10—C9—H9b	108.8
C7—N1—H1n	107 (2)	C8—C9—H9b	108.8
C8—N1—H2n	107 (3)	H9a—C9—H9b	107.7

O1—C1—C2—C3	−178.9 (4)	C2—C1—C6—C5	1.3 (6)
C6—C1—C2—C3	−0.6 (7)	O1—C1—C6—C7	0.2 (6)
C1—C2—C3—C4	0.5 (7)	C2—C1—C6—C7	−178.2 (4)
C2—C3—C4—C5	−1.1 (7)	C8—N1—C7—C6	−67.9 (4)
C2—C3—C4—Br1	177.1 (3)	C5—C6—C7—N1	−78.8 (5)
C3—C4—C5—C6	1.8 (7)	C1—C6—C7—N1	100.6 (4)
Br1—C4—C5—C6	−176.5 (3)	C7—N1—C8—C9	167.9 (4)
C4—C5—C6—C1	−1.9 (6)	N1—C8—C9—C10	−68.8 (5)
C4—C5—C6—C7	177.6 (4)	C8—C9—C10—O3	−151.6 (4)
O1—C1—C6—C5	179.7 (4)	C8—C9—C10—O2	28.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O3ⁱ	0.85 (1)	1.80 (2)	2.620 (4)	161 (5)
N1—H1n···O2	0.85 (1)	2.22 (3)	2.836 (4)	129 (3)
N1—H1n···O2ⁱⁱ	0.85 (1)	2.38 (3)	2.929 (4)	122 (3)
N1—H2n···O2ⁱⁱⁱ	0.85 (1)	2.28 (3)	2.993 (5)	141 (4)
N1—H2n···O3ⁱⁱⁱ	0.85 (1)	2.36 (3)	3.106 (5)	147 (4)

Symmetry codes: (i) −x+3/2, y−1/2, z+1/2; (ii) −x+1, −y+2, z+1/2; (iii) x, y, z+1.

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3-(5-Bromo-2-hydroxy­benzyl­ammonio)propanoate

Supporting information

Key indicators

checkCIF/PLATON results

3-(5-Bromo-2-hydroxybenzylammonio)propanoate