Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007742/cf6174sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007742/cf6174Isup2.hkl |
CCDC reference: 189314
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.005 Å
- R factor = 0.067
- wR factor = 0.181
- Data-to-parameter ratio = 19.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.20 From the CIF: _reflns_number_total 3745 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4655 Completeness (_total/calc) 80.45% Alert A: < 85% complete (theta max?)
Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.187 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.20 From the CIF: _reflns_number_total 3745 From the CIF: _diffrn_reflns_limit_ max hkl 15. 15. 15. From the CIF: _diffrn_reflns_limit_ min hkl -14. -16. -16. TEST1: Expected hkl limits for theta max Calculated maximum hkl 16. 18. 16. Calculated minimum hkl -16. -18. -16. ALERT: Expected hkl max differ from CIF values
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL972 (Sheldrick, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2001).
C4H7NO2 | F(000) = 648 |
Mr = 101.11 | Dx = 1.286 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5354 (7) Å | Cell parameters from 20830 reflections |
b = 12.7225 (12) Å | θ = 1.0–30.5° |
c = 11.8884 (10) Å | µ = 0.10 mm−1 |
β = 116.106 (3)° | T = 120 K |
V = 1566.7 (2) Å3 | Block, colourless |
Z = 12 | 0.1 × 0.1 × 0.05 mm |
Enraf-Nonius KappaCCD area-detector diffractometer | 3745 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 1343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.187 |
Detector resolution: 10.35 pixels mm-1 | θmax = 30.2°, θmin = 3.3° |
φ and ω scans | h = −14→15 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | k = −16→15 |
Tmin = 0.990, Tmax = 0.995 | l = −16→15 |
19544 measured reflections |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0693P)2] where P = (Fo2 + 2Fc2)/3 |
3745 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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 | ||
O1A | 0.4844 (2) | 0.1259 (2) | −0.1256 (2) | 0.0389 (6) | |
H1A | 0.5439 | 0.1290 | −0.1480 | 0.047* | |
O2A | 0.4289 (2) | 0.11559 (19) | 0.2320 (2) | 0.0375 (6) | |
N1A | 0.5374 (3) | 0.1276 (2) | 0.0047 (2) | 0.0309 (7) | |
C1A | 0.3082 (3) | 0.1188 (3) | −0.0316 (3) | 0.0419 (9) | |
H11A | 0.2882 | 0.1176 | −0.1207 | 0.050* | |
H12A | 0.2681 | 0.1806 | −0.0142 | 0.050* | |
H13A | 0.2745 | 0.0549 | −0.0104 | 0.050* | |
C2A | 0.4511 (3) | 0.1239 (3) | 0.0453 (3) | 0.0291 (8) | |
C3A | 0.5034 (3) | 0.1226 (3) | 0.1836 (3) | 0.0321 (8) | |
C4A | 0.6463 (3) | 0.1277 (3) | 0.2619 (3) | 0.0399 (9) | |
H41A | 0.6652 | 0.1305 | 0.3507 | 0.048* | |
H42A | 0.6806 | 0.1908 | 0.2399 | 0.048* | |
H43A | 0.6869 | 0.0652 | 0.2465 | 0.048* | |
O1B | 0.1740 (2) | 0.12470 (19) | 0.1799 (2) | 0.0429 (7) | |
H1B | 0.2481 | 0.1165 | 0.1842 | 0.052* | |
O2B | −0.0335 (2) | 0.11724 (19) | 0.4285 (2) | 0.0380 (6) | |
N1B | 0.1817 (3) | 0.1221 (2) | 0.3001 (2) | 0.0326 (7) | |
C1B | −0.0571 (3) | 0.1310 (4) | 0.1849 (3) | 0.0561 (11) | |
H11B | −0.0876 | 0.0599 | 0.1545 | 0.067* | |
H12B | −0.1202 | 0.1664 | 0.2063 | 0.067* | |
H13B | −0.0468 | 0.1708 | 0.1193 | 0.067* | |
C2B | 0.0691 (3) | 0.1245 (3) | 0.2981 (3) | 0.0330 (8) | |
C3B | 0.0711 (3) | 0.1212 (3) | 0.4227 (3) | 0.0321 (8) | |
C4B | 0.1965 (3) | 0.1228 (3) | 0.5375 (3) | 0.0459 (10) | |
H41B | 0.1812 | 0.1122 | 0.6114 | 0.055* | |
H42B | 0.2522 | 0.0666 | 0.5327 | 0.055* | |
H43B | 0.2388 | 0.1909 | 0.5438 | 0.055* | |
O1C | 0.4714 (2) | 0.36171 (19) | 0.1546 (2) | 0.0370 (6) | |
H1C | 0.4713 | 0.3673 | 0.0842 | 0.044* | |
O2C | 0.1988 (2) | 0.37064 (19) | 0.3370 (2) | 0.0424 (6) | |
N1C | 0.3454 (2) | 0.3717 (2) | 0.1411 (2) | 0.0298 (7) | |
C1C | 0.4509 (4) | 0.3447 (3) | 0.3707 (3) | 0.0475 (11) | |
H11C | 0.5277 | 0.3266 | 0.3595 | 0.057* | |
H12C | 0.4678 | 0.4085 | 0.4217 | 0.057* | |
H13C | 0.4301 | 0.2867 | 0.4131 | 0.057* | |
C2C | 0.3406 (3) | 0.3632 (3) | 0.2467 (3) | 0.0305 (8) | |
C3C | 0.2094 (3) | 0.3763 (3) | 0.2389 (3) | 0.0323 (8) | |
C4C | 0.0983 (3) | 0.3977 (3) | 0.1164 (3) | 0.0447 (10) | |
H41C | 0.1053 | 0.4693 | 0.0895 | 0.054* | |
H42C | 0.0986 | 0.3474 | 0.0541 | 0.054* | |
H43C | 0.0177 | 0.3908 | 0.1245 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0493 (15) | 0.0452 (15) | 0.0353 (14) | 0.0006 (13) | 0.0306 (12) | 0.0008 (13) |
O2A | 0.0433 (15) | 0.0400 (15) | 0.0427 (14) | 0.0002 (12) | 0.0315 (13) | 0.0025 (13) |
N1A | 0.0426 (17) | 0.0305 (16) | 0.0304 (17) | −0.0014 (14) | 0.0258 (15) | 0.0018 (14) |
C1A | 0.036 (2) | 0.052 (2) | 0.042 (2) | −0.002 (2) | 0.0221 (19) | −0.004 (2) |
C2A | 0.0342 (19) | 0.0297 (18) | 0.033 (2) | −0.0005 (17) | 0.0234 (17) | −0.0015 (16) |
C3A | 0.037 (2) | 0.0252 (19) | 0.043 (2) | 0.0034 (16) | 0.0257 (18) | 0.0008 (17) |
C4A | 0.035 (2) | 0.052 (2) | 0.037 (2) | 0.0006 (19) | 0.0195 (17) | −0.0018 (19) |
O1B | 0.0459 (15) | 0.0568 (16) | 0.0433 (16) | 0.0014 (14) | 0.0354 (13) | 0.0035 (14) |
O2B | 0.0450 (15) | 0.0409 (15) | 0.0465 (15) | −0.0004 (13) | 0.0368 (13) | 0.0010 (13) |
N1B | 0.0420 (19) | 0.0305 (16) | 0.0385 (18) | −0.0009 (15) | 0.0298 (15) | 0.0007 (14) |
C1B | 0.037 (2) | 0.097 (3) | 0.040 (2) | 0.001 (2) | 0.022 (2) | 0.004 (2) |
C2B | 0.042 (2) | 0.0307 (19) | 0.039 (2) | −0.0018 (17) | 0.0299 (18) | −0.0016 (18) |
C3B | 0.046 (2) | 0.0183 (18) | 0.042 (2) | −0.0006 (16) | 0.0275 (19) | −0.0009 (17) |
C4B | 0.044 (2) | 0.062 (3) | 0.039 (2) | 0.007 (2) | 0.026 (2) | 0.001 (2) |
O1C | 0.0380 (14) | 0.0470 (16) | 0.0403 (14) | 0.0005 (12) | 0.0303 (12) | −0.0013 (12) |
O2C | 0.0582 (16) | 0.0392 (15) | 0.0508 (16) | 0.0028 (13) | 0.0434 (14) | 0.0018 (14) |
N1C | 0.0361 (17) | 0.0324 (16) | 0.0323 (16) | 0.0028 (14) | 0.0253 (14) | −0.0002 (14) |
C1C | 0.045 (2) | 0.073 (3) | 0.030 (2) | 0.006 (2) | 0.021 (2) | −0.0024 (19) |
C2C | 0.038 (2) | 0.031 (2) | 0.030 (2) | 0.0003 (17) | 0.0216 (17) | −0.0007 (16) |
C3C | 0.038 (2) | 0.0237 (18) | 0.046 (2) | 0.0006 (18) | 0.029 (2) | 0.0007 (17) |
C4C | 0.034 (2) | 0.055 (3) | 0.051 (3) | 0.0011 (18) | 0.023 (2) | −0.0049 (19) |
O1A—N1A | 1.392 (3) | C1B—H13B | 0.980 |
O1A—H1A | 0.840 | C2B—C3B | 1.472 (4) |
O2A—C3A | 1.230 (3) | C3B—C4B | 1.490 (5) |
N1A—C2A | 1.284 (4) | C4B—H41B | 0.980 |
C1A—C2A | 1.494 (5) | C4B—H42B | 0.980 |
C1A—H11A | 0.980 | C4B—H43B | 0.980 |
C1A—H12A | 0.980 | O1C—N1C | 1.396 (3) |
C1A—H13A | 0.980 | O1C—H1C | 0.840 |
C2A—C3A | 1.481 (5) | O2C—C3C | 1.226 (4) |
C3A—C4A | 1.496 (5) | N1C—C2C | 1.285 (4) |
C4A—H41A | 0.980 | C1C—C2C | 1.482 (5) |
C4A—H42A | 0.980 | C1C—H11C | 0.980 |
C4A—H43A | 0.980 | C1C—H12C | 0.980 |
O1B—N1B | 1.393 (3) | C1C—H13C | 0.980 |
O1B—H1B | 0.840 | C2C—C3C | 1.485 (4) |
O2B—C3B | 1.239 (4) | C3C—C4C | 1.482 (5) |
N1B—C2B | 1.289 (4) | C4C—H41C | 0.980 |
C1B—C2B | 1.488 (5) | C4C—H42C | 0.980 |
C1B—H11B | 0.980 | C4C—H43C | 0.980 |
C1B—H12B | 0.980 | ||
N1A—O1A—H1A | 109.4 | C3B—C2B—C1B | 119.2 (3) |
C2A—N1A—O1A | 112.6 (3) | O2B—C3B—C2B | 118.2 (3) |
C2A—C1A—H11A | 109.5 | O2B—C3B—C4B | 121.8 (3) |
C2A—C1A—H12A | 109.4 | C2B—C3B—C4B | 120.0 (3) |
H11A—C1A—H12A | 109.5 | C3B—C4B—H41B | 109.5 |
C2A—C1A—H13A | 109.5 | C3B—C4B—H42B | 109.5 |
H11A—C1A—H13A | 109.5 | H41B—C4B—H42B | 109.5 |
H12A—C1A—H13A | 109.5 | C3B—C4B—H43B | 109.4 |
N1A—C2A—C3A | 114.4 (3) | H41B—C4B—H43B | 109.5 |
N1A—C2A—C1A | 126.9 (3) | H42B—C4B—H43B | 109.5 |
C3A—C2A—C1A | 118.7 (3) | N1C—O1C—H1C | 109.4 |
O2A—C3A—C2A | 119.5 (3) | C2C—N1C—O1C | 111.7 (2) |
O2A—C3A—C4A | 121.1 (3) | C2C—C1C—H11C | 109.4 |
C2A—C3A—C4A | 119.3 (3) | C2C—C1C—H12C | 109.5 |
C3A—C4A—H41A | 109.5 | H11C—C1C—H12C | 109.5 |
C3A—C4A—H42A | 109.4 | C2C—C1C—H13C | 109.5 |
H41A—C4A—H42A | 109.5 | H11C—C1C—H13C | 109.5 |
C3A—C4A—H43A | 109.5 | H12C—C1C—H13C | 109.5 |
H41A—C4A—H43A | 109.5 | N1C—C2C—C1C | 126.8 (3) |
H42A—C4A—H43A | 109.5 | N1C—C2C—C3C | 114.2 (3) |
N1B—O1B—H1B | 109.4 | C1C—C2C—C3C | 119.0 (3) |
C2B—N1B—O1B | 111.8 (3) | O2C—C3C—C4C | 122.7 (3) |
C2B—C1B—H11B | 109.4 | O2C—C3C—C2C | 117.3 (3) |
C2B—C1B—H12B | 109.5 | C4C—C3C—C2C | 119.9 (3) |
H11B—C1B—H12B | 109.5 | C3C—C4C—H41C | 109.4 |
C2B—C1B—H13B | 109.5 | C3C—C4C—H42C | 109.5 |
H11B—C1B—H13B | 109.5 | H41C—C4C—H42C | 109.5 |
H12B—C1B—H13B | 109.5 | C3C—C4C—H43C | 109.5 |
N1B—C2B—C3B | 114.3 (3) | H41C—C4C—H43C | 109.5 |
N1B—C2B—C1B | 126.5 (3) | H42C—C4C—H43C | 109.5 |
O1A—N1A—C2A—C3A | 178.4 (3) | C1B—C2B—C3B—O2B | 4.5 (5) |
O1A—N1A—C2A—C1A | −0.3 (5) | N1B—C2B—C3B—C4B | 4.1 (5) |
N1A—C2A—C3A—O2A | −177.6 (3) | C1B—C2B—C3B—C4B | −175.4 (4) |
C1A—C2A—C3A—O2A | 1.2 (5) | O1C—N1C—C2C—C1C | −0.2 (5) |
N1A—C2A—C3A—C4A | 1.3 (4) | O1C—N1C—C2C—C3C | 178.3 (3) |
C1A—C2A—C3A—C4A | −180.0 (3) | N1C—C2C—C3C—O2C | −178.9 (3) |
O1B—N1B—C2B—C3B | 179.6 (3) | C1C—C2C—C3C—O2C | −0.3 (5) |
O1B—N1B—C2B—C1B | −1.0 (5) | N1C—C2C—C3C—C4C | −0.3 (4) |
N1B—C2B—C3B—O2B | −176.0 (3) | C1C—C2C—C3C—C4C | 178.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O2A | 0.84 | 1.90 | 2.727 (4) | 166 |
O1A—H1A···O2Ci | 0.84 | 1.87 | 2.699 (4) | 168 |
O1C—H1C···O2Bi | 0.84 | 1.84 | 2.677 (5) | 178 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |