Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011134/hg6046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011134/hg6046Isup2.hkl |
CCDC reference: 242329
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.133
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.88
Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1875 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2141 Completeness (_total/calc) 87.58% PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.04 Ratio
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _reflns_number_total 1875 From the CIF: _diffrn_reflns_limit_ max hkl 30. 10. 10. From the CIF: _diffrn_reflns_limit_ min hkl -30. -9. -5. TEST1: Expected hkl limits for theta max Calculated maximum hkl 32. 10. 13. Calculated minimum hkl -32. -10. -13.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
2C5H11NO2·C4H6O4 | F(000) = 760 |
Mr = 352.38 | Dx = 1.316 Mg m−3 Dm = 1.32 Mg m−3 Dm measured by floatation in a mixture of xylene and bromoform |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1024 reflections |
a = 24.373 (2) Å | θ = 2.0–23.0° |
b = 7.5744 (6) Å | µ = 0.11 mm−1 |
c = 10.0284 (9) Å | T = 293 K |
β = 106.134 (2)° | Block, colorless |
V = 1778.4 (3) Å3 | 0.28 × 0.22 × 0.16 mm |
Z = 4 |
CCD area-detector diffractometer | 1875 independent reflections |
Radiation source: fine-focus sealed tube | 1620 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −30→30 |
Tmin = 0.96, Tmax = 0.99 | k = −9→10 |
5087 measured reflections | l = −5→10 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0722P)2 + 1.2632P] where P = (Fo2 + 2Fc2)/3 |
1875 reflections | (Δ/σ)max < 0.001 |
113 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.25764 (5) | −0.04824 (16) | 0.83991 (12) | 0.0347 (3) | |
O2 | 0.22223 (4) | 0.04981 (16) | 0.62358 (12) | 0.0349 (3) | |
O3 | 0.12444 (5) | 0.96157 (17) | 0.63389 (14) | 0.0402 (3) | |
H3 | 0.1544 | 1.0012 | 0.6242 | 0.060* | |
O4 | 0.08577 (5) | 1.13868 (19) | 0.45590 (14) | 0.0482 (4) | |
N1 | 0.31801 (5) | 0.19735 (16) | 0.60855 (13) | 0.0252 (3) | |
H1A | 0.3021 | 0.1357 | 0.5320 | 0.038* | |
H1B | 0.3529 | 0.2314 | 0.6080 | 0.038* | |
H1C | 0.2967 | 0.2920 | 0.6114 | 0.038* | |
C1 | 0.26185 (6) | 0.02329 (18) | 0.73212 (16) | 0.0239 (3) | |
C2 | 0.32178 (6) | 0.08532 (19) | 0.73262 (15) | 0.0232 (3) | |
H2 | 0.3364 | 0.1594 | 0.8150 | 0.028* | |
C3 | 0.36263 (7) | −0.0716 (2) | 0.74446 (18) | 0.0323 (4) | |
H3A | 0.3601 | −0.1401 | 0.8254 | 0.039* | |
C4 | 0.34551 (11) | −0.1940 (3) | 0.6215 (2) | 0.0604 (6) | |
H4A | 0.3503 | −0.1350 | 0.5407 | 0.091* | |
H4B | 0.3062 | −0.2275 | 0.6058 | 0.091* | |
H4C | 0.3691 | −0.2976 | 0.6396 | 0.091* | |
C5 | 0.42433 (9) | −0.0104 (4) | 0.7741 (4) | 0.0751 (9) | |
H5A | 0.4490 | −0.1114 | 0.7851 | 0.113* | |
H5B | 0.4343 | 0.0584 | 0.8578 | 0.113* | |
H5C | 0.4286 | 0.0603 | 0.6982 | 0.113* | |
C6 | 0.08163 (6) | 1.0302 (2) | 0.54106 (18) | 0.0314 (4) | |
C7 | 0.02524 (7) | 0.9582 (3) | 0.5489 (2) | 0.0518 (6) | |
H7A | 0.0243 | 0.8324 | 0.5303 | 0.062* | |
H7B | 0.0224 | 0.9738 | 0.6428 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0302 (6) | 0.0438 (7) | 0.0313 (7) | −0.0069 (5) | 0.0108 (5) | 0.0097 (5) |
O2 | 0.0198 (5) | 0.0498 (7) | 0.0339 (7) | −0.0044 (5) | 0.0055 (4) | 0.0091 (5) |
O3 | 0.0213 (5) | 0.0481 (7) | 0.0503 (8) | −0.0028 (5) | 0.0085 (5) | 0.0135 (6) |
O4 | 0.0249 (6) | 0.0611 (9) | 0.0579 (8) | −0.0054 (5) | 0.0103 (5) | 0.0244 (7) |
N1 | 0.0191 (5) | 0.0276 (6) | 0.0303 (7) | −0.0007 (4) | 0.0091 (5) | 0.0041 (5) |
C1 | 0.0223 (7) | 0.0234 (7) | 0.0277 (8) | −0.0016 (5) | 0.0099 (6) | 0.0001 (6) |
C2 | 0.0204 (6) | 0.0274 (7) | 0.0218 (7) | −0.0014 (5) | 0.0058 (5) | 0.0008 (5) |
C3 | 0.0278 (7) | 0.0347 (8) | 0.0359 (9) | 0.0079 (6) | 0.0116 (6) | 0.0102 (7) |
C4 | 0.0863 (16) | 0.0470 (11) | 0.0491 (13) | 0.0283 (11) | 0.0211 (11) | −0.0015 (9) |
C5 | 0.0275 (10) | 0.0699 (16) | 0.128 (3) | 0.0117 (10) | 0.0217 (12) | 0.0267 (15) |
C6 | 0.0215 (7) | 0.0338 (8) | 0.0398 (10) | −0.0029 (6) | 0.0102 (6) | 0.0020 (7) |
C7 | 0.0215 (8) | 0.0637 (13) | 0.0688 (14) | −0.0050 (8) | 0.0104 (8) | 0.0285 (11) |
O1—C1 | 1.2386 (19) | C3—C5 | 1.522 (3) |
O2—C1 | 1.2543 (18) | C3—H3A | 0.9800 |
O3—C6 | 1.299 (2) | C4—H4A | 0.9600 |
O3—H3 | 0.8200 | C4—H4B | 0.9600 |
O4—C6 | 1.209 (2) | C4—H4C | 0.9600 |
N1—C2 | 1.4876 (18) | C5—H5A | 0.9600 |
N1—H1A | 0.8900 | C5—H5B | 0.9600 |
N1—H1B | 0.8900 | C5—H5C | 0.9600 |
N1—H1C | 0.8900 | C6—C7 | 1.501 (2) |
C1—C2 | 1.5331 (19) | C7—C7i | 1.486 (4) |
C2—C3 | 1.534 (2) | C7—H7A | 0.9700 |
C2—H2 | 0.9800 | C7—H7B | 0.9700 |
C3—C4 | 1.506 (3) | ||
C6—O3—H3 | 109.5 | C3—C4—H4A | 109.5 |
C2—N1—H1A | 109.5 | C3—C4—H4B | 109.5 |
C2—N1—H1B | 109.5 | H4A—C4—H4B | 109.5 |
H1A—N1—H1B | 109.5 | C3—C4—H4C | 109.5 |
C2—N1—H1C | 109.5 | H4A—C4—H4C | 109.5 |
H1A—N1—H1C | 109.5 | H4B—C4—H4C | 109.5 |
H1B—N1—H1C | 109.5 | C3—C5—H5A | 109.5 |
O1—C1—O2 | 126.64 (13) | C3—C5—H5B | 109.5 |
O1—C1—C2 | 116.18 (13) | H5A—C5—H5B | 109.5 |
O2—C1—C2 | 117.18 (13) | C3—C5—H5C | 109.5 |
N1—C2—C1 | 109.55 (11) | H5A—C5—H5C | 109.5 |
N1—C2—C3 | 113.25 (12) | H5B—C5—H5C | 109.5 |
C1—C2—C3 | 111.11 (12) | O4—C6—O3 | 124.78 (14) |
N1—C2—H2 | 107.6 | O4—C6—C7 | 122.78 (15) |
C1—C2—H2 | 107.6 | O3—C6—C7 | 112.43 (14) |
C3—C2—H2 | 107.6 | C7i—C7—C6 | 114.36 (19) |
C4—C3—C5 | 112.42 (19) | C7i—C7—H7A | 108.7 |
C4—C3—C2 | 112.80 (14) | C6—C7—H7A | 108.7 |
C5—C3—C2 | 111.35 (15) | C7i—C7—H7B | 108.7 |
C4—C3—H3A | 106.6 | C6—C7—H7B | 108.7 |
C5—C3—H3A | 106.6 | H7A—C7—H7B | 107.6 |
C2—C3—H3A | 106.6 | ||
O1—C1—C2—N1 | −169.28 (13) | C1—C2—C3—C4 | 63.94 (19) |
O2—C1—C2—N1 | 10.68 (18) | N1—C2—C3—C5 | 67.6 (2) |
O1—C1—C2—C3 | 64.83 (17) | C1—C2—C3—C5 | −168.58 (17) |
O2—C1—C2—C3 | −115.20 (15) | O4—C6—C7—C7i | −4.7 (4) |
N1—C2—C3—C4 | −59.87 (19) | O3—C6—C7—C7i | 176.0 (3) |
Symmetry code: (i) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2ii | 0.82 | 1.70 | 2.5050 (15) | 169 |
N1—H1B···O4iii | 0.89 | 2.04 | 2.8814 (16) | 158 |
N1—H1C···O1iv | 0.89 | 1.95 | 2.8124 (16) | 162 |
N1—H1A···O1v | 0.89 | 2.04 | 2.9147 (17) | 167 |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1/2, −y+3/2, −z+1; (iv) −x+1/2, y+1/2, −z+3/2; (v) x, −y, z−1/2. |