Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019754/cf6128sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019754/cf6128Isup2.hkl |
CCDC reference: 177229
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.087
- Data-to-parameter ratio = 7.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.40 From the CIF: _reflns_number_total 1086 Count of symmetry unique reflns 1080 Completeness (_total/calc) 100.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 6 Fraction of Friedel pairs measured 0.006 Are heavy atom types Z>Si present no 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.
Data collection: CAD4 (Enraf-Nonius, 1992); cell refinement: SET4 and CELDIM (Enraf-Nonius, 1992); data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).
C11H11NO3 | Dx = 1.403 Mg m−3 |
Mr = 205.21 | Melting point: 485 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 5.1787 (5) Å | θ = 9.0–18.9° |
b = 9.9128 (18) Å | µ = 0.10 mm−1 |
c = 18.918 (5) Å | T = 294 K |
V = 971.2 (3) Å3 | Plate, colourless |
Z = 4 | 0.42 × 0.21 × 0.04 mm |
F(000) = 432 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.024 |
Radiation source: X-ray tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −6→6 |
ω–2θ scans | k = −11→11 |
1803 measured reflections | l = −22→22 |
1086 independent reflections | 3 standard reflections every 240 min |
866 reflections with I > 2σ(I) | intensity decay: 0.5% |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0513P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
1086 reflections | Δρmax = 0.15 e Å−3 |
139 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (3) |
Geometry. Mean plane data ex-SHELXL97 for molecule (I) ############################################ -3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240) * 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9 0.0349 (0.0046) N1 0.1198 (0.0052) O3 0.0496 (0.0044) C3 0.0324 (0.0042) C10 Rms deviation of fitted atoms = 0.0014 -3.5692(0.0050)x + 6.8088(0.0093)y + 4.3640(0.0243)z = 2.8396(0.0222) Angle to previous plane (with approximate e.s.d.) = 1.21 (18) * -0.0125 (0.0016) N1 * 0.0115 (0.0015) C3 * -0.0058 (0.0015) C4 * -0.0010 (0.0016) C9 * 0.0078 (0.0015) C10 0.0664 (0.0037) O3 1.6122 (0.0047) C1 0.2270 (0.0044) C2 Rms deviation of fitted atoms = 0.0088 2.4277(0.0068)x + 8.5399(0.0077)y + 3.6905(0.0250)z = 6.0406(0.0183) Angle to previous plane (with approximate e.s.d.) = 71.72 (9) * 0.0062 (0.0007) O1 * 0.0076 (0.0009) O2 * -0.0191 (0.0022) C1 * 0.0053 (0.0006) C2 - 0.5248 (0.0042) N1 - 2.6141 (0.0031) O3 - 1.7542 (0.0044) C3 Rms deviation of fitted atoms = 0.0111 -3.5683(0.0045)x + 6.8741(0.0085)y + 3.9846(0.0239)z = 2.4843(0.0240) Angle to previous plane (with approximate e.s.d.) = 71.61 (8) * 0.0011 (0.0018) C4 * 0.0010 (0.0020) C5 * -0.0020 (0.0022) C6 * 0.0009 (0.0022) C7 * 0.0011 (0.0021) C8 * -0.0021 (0.0019) C9 Rms deviation of fitted atoms = 0.0014 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2219 (4) | 0.3422 (2) | 0.70076 (9) | 0.0436 (5) | |
O2 | 0.1185 (4) | 0.3225 (2) | 0.81453 (9) | 0.0448 (6) | |
O3 | 0.1743 (4) | 0.00701 (19) | 0.79755 (9) | 0.0431 (5) | |
N1 | 0.5015 (4) | 0.1415 (2) | 0.83717 (10) | 0.0322 (5) | |
C1 | 0.2613 (6) | 0.2997 (3) | 0.76625 (14) | 0.0319 (6) | |
C2 | 0.5186 (5) | 0.2258 (3) | 0.77452 (12) | 0.0336 (6) | |
C3 | 0.3211 (5) | 0.0455 (2) | 0.84486 (13) | 0.0322 (6) | |
C4 | 0.3303 (5) | 0.0001 (2) | 0.91926 (13) | 0.0330 (6) | |
C5 | 0.1849 (6) | −0.0953 (3) | 0.95365 (15) | 0.0466 (8) | |
C6 | 0.2280 (7) | −0.1147 (3) | 1.02500 (16) | 0.0554 (9) | |
C7 | 0.4113 (7) | −0.0391 (3) | 1.05950 (15) | 0.0572 (9) | |
C8 | 0.5580 (6) | 0.0569 (3) | 1.02528 (15) | 0.0508 (9) | |
C9 | 0.5160 (5) | 0.0761 (3) | 0.95383 (13) | 0.0367 (6) | |
C10 | 0.6353 (5) | 0.1726 (3) | 0.90280 (13) | 0.0405 (7) | |
C11 | 0.6091 (6) | 0.1497 (3) | 0.70982 (14) | 0.0442 (8) | |
H1 | 0.0983 | 0.3938 | 0.7001 | 0.065* | |
H2 | 0.6494 | 0.2948 | 0.7844 | 0.040* | |
H5 | 0.0610 | −0.1454 | 0.9296 | 0.056* | |
H6 | 0.1330 | −0.1789 | 1.0497 | 0.067* | |
H7 | 0.4373 | −0.0532 | 1.1076 | 0.069* | |
H8 | 0.6812 | 0.1072 | 1.0495 | 0.061* | |
H10A | 0.6056 | 0.2653 | 0.9170 | 0.049* | |
H10B | 0.8195 | 0.1572 | 0.8984 | 0.049* | |
H11A | 0.7728 | 0.1082 | 0.7195 | 0.066* | |
H11B | 0.6269 | 0.2112 | 0.6709 | 0.066* | |
H11C | 0.4850 | 0.0814 | 0.6980 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0367 (11) | 0.0525 (12) | 0.0415 (11) | 0.0129 (11) | −0.0004 (9) | 0.0086 (9) |
O2 | 0.0356 (12) | 0.0555 (14) | 0.0432 (11) | 0.0109 (10) | 0.0066 (9) | 0.0017 (10) |
O3 | 0.0423 (12) | 0.0474 (11) | 0.0398 (10) | −0.0156 (12) | −0.0101 (10) | 0.0011 (9) |
N1 | 0.0268 (11) | 0.0351 (11) | 0.0346 (12) | −0.0030 (11) | −0.0047 (11) | 0.0020 (9) |
C1 | 0.0296 (14) | 0.0298 (14) | 0.0361 (14) | −0.0031 (12) | −0.0020 (13) | 0.0015 (11) |
C2 | 0.0254 (14) | 0.0331 (13) | 0.0421 (15) | −0.0032 (14) | −0.0012 (14) | 0.0010 (12) |
C3 | 0.0313 (15) | 0.0297 (14) | 0.0355 (13) | 0.0004 (12) | −0.0016 (13) | 0.0001 (11) |
C4 | 0.0310 (15) | 0.0323 (14) | 0.0358 (13) | 0.0052 (14) | 0.0016 (12) | 0.0000 (12) |
C5 | 0.0481 (19) | 0.0442 (16) | 0.0475 (17) | −0.0025 (15) | 0.0007 (16) | 0.0029 (14) |
C6 | 0.058 (2) | 0.062 (2) | 0.0467 (17) | 0.0016 (19) | 0.0083 (18) | 0.0145 (15) |
C7 | 0.060 (2) | 0.076 (2) | 0.0359 (16) | 0.014 (2) | 0.0000 (16) | 0.0101 (15) |
C8 | 0.0430 (19) | 0.069 (2) | 0.0406 (16) | −0.0017 (17) | −0.0064 (15) | −0.0016 (15) |
C9 | 0.0297 (14) | 0.0457 (15) | 0.0346 (13) | 0.0050 (14) | −0.0017 (13) | −0.0025 (12) |
C10 | 0.0297 (15) | 0.0476 (16) | 0.0440 (15) | −0.0024 (15) | −0.0065 (13) | −0.0056 (13) |
C11 | 0.0408 (18) | 0.0467 (16) | 0.0452 (16) | 0.0089 (16) | 0.0058 (14) | 0.0015 (14) |
O1—C1 | 1.324 (3) | C8—C9 | 1.382 (4) |
O2—C1 | 1.197 (3) | C9—C10 | 1.493 (4) |
O3—C3 | 1.235 (3) | O1—H1 | 0.82 |
N1—C2 | 1.453 (3) | C2—H2 | 0.98 |
N1—C3 | 1.342 (3) | C5—H5 | 0.93 |
N1—C10 | 1.455 (3) | C6—H6 | 0.93 |
C1—C2 | 1.528 (4) | C7—H7 | 0.93 |
C2—C11 | 1.512 (4) | C8—H8 | 0.93 |
C3—C4 | 1.479 (4) | C10—H10A | 0.97 |
C4—C5 | 1.373 (4) | C10—H10B | 0.97 |
C4—C9 | 1.385 (4) | C11—H11A | 0.96 |
C5—C6 | 1.382 (4) | C11—H11B | 0.96 |
C6—C7 | 1.374 (5) | C11—H11C | 0.96 |
C7—C8 | 1.380 (4) | ||
C2—N1—C3 | 122.6 (2) | C1—O1—H1 | 109.5 |
C2—N1—C10 | 123.1 (2) | N1—C2—H2 | 106.7 |
C3—N1—C10 | 112.9 (2) | C11—C2—H2 | 106.7 |
O1—C1—O2 | 123.9 (3) | C1—C2—H2 | 106.7 |
O1—C1—C2 | 112.5 (2) | C4—C5—H5 | 121.0 |
O2—C1—C2 | 123.5 (2) | C6—C5—H5 | 121.0 |
N1—C2—C1 | 107.8 (2) | C7—C6—H6 | 120.0 |
N1—C2—C11 | 113.1 (2) | C5—C6—H6 | 120.0 |
C1—C2—C11 | 115.2 (2) | C6—C7—H7 | 118.9 |
O3—C3—N1 | 124.7 (2) | C8—C7—H7 | 118.9 |
O3—C3—C4 | 128.0 (2) | C7—C8—H8 | 121.1 |
N1—C3—C4 | 107.3 (2) | C9—C8—H8 | 121.1 |
C3—C4—C5 | 130.0 (3) | N1—C10—H10A | 111.2 |
C3—C4—C9 | 107.9 (2) | C9—C10—H10A | 111.2 |
C5—C4—C9 | 122.1 (2) | N1—C10—H10B | 111.2 |
C4—C5—C6 | 118.1 (3) | C9—C10—H10B | 111.2 |
C5—C6—C7 | 120.0 (3) | H10A—C10—H10B | 109.1 |
C6—C7—C8 | 122.3 (3) | C2—C11—H11A | 109.5 |
C7—C8—C9 | 117.8 (3) | C2—C11—H11B | 109.5 |
C4—C9—C8 | 119.8 (3) | H11A—C11—H11B | 109.5 |
C4—C9—C10 | 109.3 (2) | C2—C11—H11C | 109.5 |
C8—C9—C10 | 130.9 (3) | H11A—C11—H11C | 109.5 |
N1—C10—C9 | 102.7 (2) | H11B—C11—H11C | 109.5 |
C3—N1—C2—C1 | 58.3 (3) | C9—C4—C5—C6 | 0.0 (4) |
C10—N1—C2—C1 | −107.1 (3) | C3—C4—C5—C6 | −177.7 (3) |
C3—N1—C2—C11 | −70.3 (3) | C4—C5—C6—C7 | 0.3 (4) |
C10—N1—C2—C11 | 124.3 (3) | C5—C6—C7—C8 | −0.3 (5) |
O2—C1—C2—N1 | 25.0 (4) | C6—C7—C8—C9 | 0.0 (5) |
O1—C1—C2—N1 | −158.7 (2) | C7—C8—C9—C4 | 0.3 (4) |
O2—C1—C2—C11 | 152.4 (3) | C7—C8—C9—C10 | 178.2 (3) |
O1—C1—C2—C11 | −31.3 (3) | C5—C4—C9—C8 | −0.3 (4) |
C2—N1—C3—O3 | 9.6 (4) | C3—C4—C9—C8 | 177.8 (3) |
C10—N1—C3—O3 | 176.3 (2) | C5—C4—C9—C10 | −178.6 (2) |
C2—N1—C3—C4 | −169.1 (2) | C3—C4—C9—C10 | −0.5 (3) |
C10—N1—C3—C4 | −2.3 (3) | C3—N1—C10—C9 | 2.0 (3) |
O3—C3—C4—C5 | 1.1 (5) | C2—N1—C10—C9 | 168.6 (2) |
N1—C3—C4—C5 | 179.7 (3) | C8—C9—C10—N1 | −178.9 (3) |
O3—C3—C4—C9 | −176.9 (3) | C4—C9—C10—N1 | −0.8 (3) |
N1—C3—C4—C9 | 1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.80 | 2.623 (3) | 178 |
C2—H2···O2ii | 0.98 | 2.51 | 3.338 (4) | 142 |
C11—H11C···O3 | 0.96 | 2.58 | 3.135 (4) | 117 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1, y, z. |