In the title compound, C
6H
11NO
4, the ψ
1 and ψ
2 torsion angles are −34.1 (3) and 149.1 (4)°, respectively. Atom C
γ is
gauche to N and atom C
δ is
trans to C
α. Translationally and screw-related molecules are connected by N—H
O hydrogen bonds to form layers parallel to the
ab plane.
Supporting information
CCDC reference: 289693
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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.
Crystal data top
C6H11NO4 | F(000) = 344 |
Mr = 161.16 | Dx = 1.364 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 1287 reflections |
a = 10.286 (3) Å | θ = 2.5–28.2° |
b = 4.6163 (11) Å | µ = 0.12 mm−1 |
c = 17.111 (4) Å | T = 292 K |
β = 104.995 (4)° | Plate, colourless |
V = 784.9 (3) Å3 | 0.30 × 0.30 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 953 independent reflections |
Radiation source: fine-focus sealed tube | 903 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 27.0°, θmin = 1.2° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = 0→5 |
Tmin = 0.963, Tmax = 0.993 | l = 0→21 |
953 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-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 parameters | Δρmax = 0.42 e Å−3 |
4 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2127 (3) | 0.4738 (8) | 0.60637 (14) | 0.0273 (6) | |
C2 | 0.3459 (2) | 0.3193 (8) | 0.64331 (15) | 0.0261 (6) | |
H2 | 0.3286 | 0.1136 | 0.6506 | 0.031* | |
C3 | 0.4147 (3) | 0.4535 (9) | 0.72532 (15) | 0.0344 (7) | |
H3A | 0.4239 | 0.6604 | 0.7184 | 0.041* | |
H3B | 0.3577 | 0.4254 | 0.7619 | 0.041* | |
C4 | 0.5530 (4) | 0.3257 (11) | 0.7636 (2) | 0.0563 (11) | |
H4A | 0.5425 | 0.1235 | 0.7761 | 0.068* | |
H4B | 0.6066 | 0.3337 | 0.7246 | 0.068* | |
C5 | 0.6271 (3) | 0.4781 (12) | 0.83899 (18) | 0.0444 (8) | |
C6 | 0.8409 (4) | 0.547 (2) | 0.9280 (3) | 0.086 (2) | |
H6A | 0.7941 | 0.5516 | 0.9697 | 0.129* | |
H6B | 0.8638 | 0.7407 | 0.9162 | 0.129* | |
H6C | 0.9216 | 0.4343 | 0.9459 | 0.129* | |
N1 | 0.4338 (2) | 0.3484 (6) | 0.58715 (13) | 0.0324 (6) | |
H1A | 0.4737 | 0.5210 | 0.5940 | 0.049* | |
H1B | 0.3842 | 0.3319 | 0.5364 | 0.049* | |
H1C | 0.4960 | 0.2099 | 0.5975 | 0.049* | |
O1 | 0.2185 (2) | 0.6965 (7) | 0.56569 (12) | 0.0369 (5) | |
O2 | 0.1091 (2) | 0.3752 (8) | 0.62247 (15) | 0.0423 (6) | |
O3 | 0.5802 (3) | 0.6370 (16) | 0.8783 (2) | 0.1043 (18) | |
O4 | 0.7557 (3) | 0.4178 (12) | 0.85608 (17) | 0.0805 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0225 (12) | 0.0239 (12) | 0.0331 (11) | 0.0039 (10) | 0.0028 (9) | −0.0076 (10) |
C2 | 0.0198 (10) | 0.0187 (12) | 0.0383 (12) | 0.0030 (10) | 0.0046 (9) | −0.0004 (10) |
C3 | 0.0284 (13) | 0.0388 (16) | 0.0319 (11) | 0.0063 (12) | 0.0005 (10) | −0.0004 (11) |
C4 | 0.0463 (18) | 0.055 (2) | 0.0515 (17) | 0.0237 (19) | −0.0163 (15) | −0.0178 (17) |
C5 | 0.0353 (14) | 0.0556 (19) | 0.0359 (12) | 0.0069 (16) | −0.0026 (11) | −0.0030 (15) |
C6 | 0.041 (2) | 0.144 (6) | 0.060 (2) | −0.002 (3) | −0.0115 (17) | −0.026 (3) |
N1 | 0.0204 (10) | 0.0370 (13) | 0.0374 (10) | 0.0049 (11) | 0.0033 (8) | −0.0096 (11) |
O1 | 0.0307 (10) | 0.0331 (12) | 0.0427 (10) | 0.0092 (9) | 0.0017 (8) | 0.0064 (9) |
O2 | 0.0211 (9) | 0.0369 (12) | 0.0699 (13) | 0.0013 (9) | 0.0135 (8) | −0.0047 (11) |
O3 | 0.0531 (18) | 0.158 (5) | 0.084 (2) | 0.028 (3) | −0.0141 (15) | −0.067 (3) |
O4 | 0.0394 (13) | 0.128 (4) | 0.0597 (15) | 0.021 (2) | −0.0126 (11) | −0.034 (2) |
Geometric parameters (Å, º) top
C1—O1 | 1.252 (6) | C4—H4B | 0.97 |
C1—O2 | 1.253 (4) | C5—O3 | 1.179 (7) |
C1—C2 | 1.529 (3) | C5—O4 | 1.309 (5) |
C2—N1 | 1.486 (3) | C6—O4 | 1.442 (6) |
C2—C3 | 1.530 (4) | C6—H6A | 0.96 |
C2—H2 | 0.98 | C6—H6B | 0.96 |
C3—C4 | 1.523 (4) | C6—H6C | 0.96 |
C3—H3A | 0.97 | N1—H1A | 0.89 |
C3—H3B | 0.97 | N1—H1B | 0.89 |
C4—C5 | 1.494 (5) | N1—H1C | 0.89 |
C4—H4A | 0.97 | | |
| | | |
O1—C1—O2 | 125.9 (3) | C3—C4—H4B | 108.9 |
O1—C1—C2 | 116.5 (2) | H4A—C4—H4B | 107.7 |
O2—C1—C2 | 117.5 (3) | O3—C5—O4 | 122.9 (4) |
N1—C2—C1 | 108.7 (2) | O3—C5—C4 | 126.4 (3) |
N1—C2—C3 | 110.0 (2) | O4—C5—C4 | 110.7 (4) |
C1—C2—C3 | 110.0 (2) | O4—C6—H6A | 109.5 |
N1—C2—H2 | 109.4 | O4—C6—H6B | 109.5 |
C1—C2—H2 | 109.4 | H6A—C6—H6B | 109.5 |
C3—C2—H2 | 109.4 | O4—C6—H6C | 109.5 |
C4—C3—C2 | 113.4 (2) | H6A—C6—H6C | 109.5 |
C4—C3—H3A | 108.9 | H6B—C6—H6C | 109.5 |
C2—C3—H3A | 108.9 | C2—N1—H1A | 109.5 |
C4—C3—H3B | 108.9 | C2—N1—H1B | 109.5 |
C2—C3—H3B | 108.9 | H1A—N1—H1B | 109.5 |
H3A—C3—H3B | 107.7 | C2—N1—H1C | 109.5 |
C5—C4—C3 | 113.6 (3) | H1A—N1—H1C | 109.5 |
C5—C4—H4A | 108.9 | H1B—N1—H1C | 109.5 |
C3—C4—H4A | 108.9 | C5—O4—C6 | 117.3 (5) |
C5—C4—H4B | 108.9 | | |
| | | |
O1—C1—C2—N1 | −34.1 (3) | C2—C3—C4—C5 | 173.5 (3) |
O2—C1—C2—N1 | 149.1 (4) | C3—C4—C5—O3 | 16.6 (8) |
O1—C1—C2—C3 | 86.4 (3) | C3—C4—C5—O4 | −161.9 (5) |
O2—C1—C2—C3 | −90.4 (3) | O3—C5—O4—C6 | 2.1 (11) |
N1—C2—C3—C4 | −56.2 (4) | C4—C5—O4—C6 | −179.4 (6) |
C1—C2—C3—C4 | −176.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1i | 0.89 | 1.90 | 2.769 (3) | 166 |
N1—H1A···O2ii | 0.89 | 2.12 | 2.994 (4) | 167 |
N1—H1C···O2iii | 0.89 | 1.91 | 2.797 (4) | 171 |
N1—H1C···O1iii | 0.89 | 2.49 | 3.124 (3) | 129 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y−1/2, z. |