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In the title compound, C6H11NO4, the ψ1 and ψ2 torsion angles are −34.1 (3) and 149.1 (4)°, respectively. Atom Cγ is gauche to N and atom Cδ is trans to Cα. Translationally and screw-related mol­ecules are connected by N—H...O hydrogen bonds to form layers parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032952/ci6645sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032952/ci6645Isup2.hkl
Contains datablock I

CCDC reference: 289693

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.160
  • Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.16 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C5
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.83 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.05 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H6C .. H6C .. 2.12 Ang.
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 27.00 From the CIF: _reflns_number_total 953 Count of symmetry unique reflns 958 Completeness (_total/calc) 99.48% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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, 2001); cell refinement: SAINT-Plus (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.

5-Methyl L-glutamate top
Crystal data top
C6H11NO4F(000) = 344
Mr = 161.16Dx = 1.364 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1287 reflections
a = 10.286 (3) Åθ = 2.5–28.2°
b = 4.6163 (11) ŵ = 0.12 mm1
c = 17.111 (4) ÅT = 292 K
β = 104.995 (4)°Plate, colourless
V = 784.9 (3) Å30.30 × 0.30 × 0.06 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
953 independent reflections
Radiation source: fine-focus sealed tube903 reflections with I > 2σ(I)
Graphite monochromatorθmax = 27.0°, θmin = 1.2°
φ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 05
Tmin = 0.963, Tmax = 0.993l = 021
953 measured reflections
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.1191P)2 + 0.0947P]
where P = (Fo2 + 2Fc2)/3
953 reflections(Δ/σ)max = 0.001
103 parametersΔρmax = 0.42 e Å3
4 restraintsΔρmin = 0.28 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
C10.2127 (3)0.4738 (8)0.60637 (14)0.0273 (6)
C20.3459 (2)0.3193 (8)0.64331 (15)0.0261 (6)
H20.32860.11360.65060.031*
C30.4147 (3)0.4535 (9)0.72532 (15)0.0344 (7)
H3A0.42390.66040.71840.041*
H3B0.35770.42540.76190.041*
C40.5530 (4)0.3257 (11)0.7636 (2)0.0563 (11)
H4A0.54250.12350.77610.068*
H4B0.60660.33370.72460.068*
C50.6271 (3)0.4781 (12)0.83899 (18)0.0444 (8)
C60.8409 (4)0.547 (2)0.9280 (3)0.086 (2)
H6A0.79410.55160.96970.129*
H6B0.86380.74070.91620.129*
H6C0.92160.43430.94590.129*
N10.4338 (2)0.3484 (6)0.58715 (13)0.0324 (6)
H1A0.47370.52100.59400.049*
H1B0.38420.33190.53640.049*
H1C0.49600.20990.59750.049*
O10.2185 (2)0.6965 (7)0.56569 (12)0.0369 (5)
O20.1091 (2)0.3752 (8)0.62247 (15)0.0423 (6)
O30.5802 (3)0.6370 (16)0.8783 (2)0.1043 (18)
O40.7557 (3)0.4178 (12)0.85608 (17)0.0805 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0225 (12)0.0239 (12)0.0331 (11)0.0039 (10)0.0028 (9)0.0076 (10)
C20.0198 (10)0.0187 (12)0.0383 (12)0.0030 (10)0.0046 (9)0.0004 (10)
C30.0284 (13)0.0388 (16)0.0319 (11)0.0063 (12)0.0005 (10)0.0004 (11)
C40.0463 (18)0.055 (2)0.0515 (17)0.0237 (19)0.0163 (15)0.0178 (17)
C50.0353 (14)0.0556 (19)0.0359 (12)0.0069 (16)0.0026 (11)0.0030 (15)
C60.041 (2)0.144 (6)0.060 (2)0.002 (3)0.0115 (17)0.026 (3)
N10.0204 (10)0.0370 (13)0.0374 (10)0.0049 (11)0.0033 (8)0.0096 (11)
O10.0307 (10)0.0331 (12)0.0427 (10)0.0092 (9)0.0017 (8)0.0064 (9)
O20.0211 (9)0.0369 (12)0.0699 (13)0.0013 (9)0.0135 (8)0.0047 (11)
O30.0531 (18)0.158 (5)0.084 (2)0.028 (3)0.0141 (15)0.067 (3)
O40.0394 (13)0.128 (4)0.0597 (15)0.021 (2)0.0126 (11)0.034 (2)
Geometric parameters (Å, º) top
C1—O11.252 (6)C4—H4B0.97
C1—O21.253 (4)C5—O31.179 (7)
C1—C21.529 (3)C5—O41.309 (5)
C2—N11.486 (3)C6—O41.442 (6)
C2—C31.530 (4)C6—H6A0.96
C2—H20.98C6—H6B0.96
C3—C41.523 (4)C6—H6C0.96
C3—H3A0.97N1—H1A0.89
C3—H3B0.97N1—H1B0.89
C4—C51.494 (5)N1—H1C0.89
C4—H4A0.97
O1—C1—O2125.9 (3)C3—C4—H4B108.9
O1—C1—C2116.5 (2)H4A—C4—H4B107.7
O2—C1—C2117.5 (3)O3—C5—O4122.9 (4)
N1—C2—C1108.7 (2)O3—C5—C4126.4 (3)
N1—C2—C3110.0 (2)O4—C5—C4110.7 (4)
C1—C2—C3110.0 (2)O4—C6—H6A109.5
N1—C2—H2109.4O4—C6—H6B109.5
C1—C2—H2109.4H6A—C6—H6B109.5
C3—C2—H2109.4O4—C6—H6C109.5
C4—C3—C2113.4 (2)H6A—C6—H6C109.5
C4—C3—H3A108.9H6B—C6—H6C109.5
C2—C3—H3A108.9C2—N1—H1A109.5
C4—C3—H3B108.9C2—N1—H1B109.5
C2—C3—H3B108.9H1A—N1—H1B109.5
H3A—C3—H3B107.7C2—N1—H1C109.5
C5—C4—C3113.6 (3)H1A—N1—H1C109.5
C5—C4—H4A108.9H1B—N1—H1C109.5
C3—C4—H4A108.9C5—O4—C6117.3 (5)
C5—C4—H4B108.9
O1—C1—C2—N134.1 (3)C2—C3—C4—C5173.5 (3)
O2—C1—C2—N1149.1 (4)C3—C4—C5—O316.6 (8)
O1—C1—C2—C386.4 (3)C3—C4—C5—O4161.9 (5)
O2—C1—C2—C390.4 (3)O3—C5—O4—C62.1 (11)
N1—C2—C3—C456.2 (4)C4—C5—O4—C6179.4 (6)
C1—C2—C3—C4176.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.891.902.769 (3)166
N1—H1A···O2ii0.892.122.994 (4)167
N1—H1C···O2iii0.891.912.797 (4)171
N1—H1C···O1iii0.892.493.124 (3)129
Symmetry codes: (i) x+1/2, y1/2, z+1; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z.
 

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