Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051816/bh2062sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051816/bh2062Isup2.hkl |
CCDC reference: 633601
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.106
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C2 .. 3.00 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C12 .. 3.00 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 27.84 From the CIF: _reflns_number_total 2246 Count of symmetry unique reflns 2268 Completeness (_total/calc) 99.03% 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 PLAT792_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C13 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
C10H11NO3 | Dx = 1.371 Mg m−3 |
Mr = 193.20 | Melting point: 421 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3044 reflections |
a = 7.8287 (8) Å | θ = 2.0–27.8° |
b = 7.8026 (8) Å | µ = 0.10 mm−1 |
c = 30.6427 (18) Å | T = 113 K |
V = 1871.8 (3) Å3 | Plate, colourless |
Z = 8 | 0.22 × 0.20 × 0.10 mm |
F(000) = 816 |
Rigaku Saturn diffractometer | 2246 independent reflections |
Radiation source: rotating anode | 2179 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.043 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.8°, θmin = 2.7° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −10→9 |
Tmin = 0.968, Tmax = 0.990 | l = −40→40 |
13397 measured reflections |
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0563P)2 + 0.3587P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2246 reflections | Δρmax = 0.30 e Å−3 |
266 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
Experimental. IR (KBr pellet, cm-1): 3310m, 3029m, 2759w, 1690 s, 1653w, 1495w, 1460w, 1417w, 1372w, 1320m, 1296w, 1230w, 1142m, 1119w, 1092w, 1033m, 938m, 775m, 730w, 705m, 621w, 585w, 545m. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2845 (3) | 0.4441 (3) | 0.11620 (7) | 0.0204 (4) | |
H1 | 0.379 (4) | 0.392 (4) | 0.1169 (12) | 0.031* | |
N2 | 0.1184 (3) | 0.4421 (3) | 0.22242 (7) | 0.0208 (4) | |
H2 | 0.004 (4) | 0.389 (4) | 0.2181 (10) | 0.031* | |
O1 | 0.1027 (2) | 0.2155 (2) | 0.11770 (6) | 0.0218 (4) | |
O2 | 0.2848 (2) | 0.6215 (2) | 0.10854 (6) | 0.0232 (4) | |
O3 | −0.1284 (3) | 0.5087 (2) | 0.13906 (6) | 0.0204 (4) | |
H3 | −0.211 (5) | 0.445 (4) | 0.1319 (12) | 0.031* | |
O4 | 0.2991 (2) | 0.2147 (2) | 0.22006 (6) | 0.0227 (4) | |
O5 | 0.1185 (2) | 0.6211 (2) | 0.23074 (6) | 0.0227 (4) | |
O6 | 0.5307 (2) | 0.5085 (2) | 0.19898 (6) | 0.0211 (4) | |
H6 | 0.605 (4) | 0.423 (4) | 0.2049 (11) | 0.032* | |
C1 | 0.1325 (3) | 0.3724 (3) | 0.11398 (8) | 0.0177 (5) | |
C2 | 0.1083 (3) | 0.6741 (3) | 0.11480 (9) | 0.0194 (5) | |
H2A | 0.0775 | 0.7658 | 0.0939 | 0.023* | |
H2B | 0.0908 | 0.7174 | 0.1448 | 0.023* | |
C3 | −0.0006 (3) | 0.5142 (3) | 0.10679 (8) | 0.0180 (5) | |
C4 | −0.0781 (4) | 0.5002 (3) | 0.06049 (9) | 0.0214 (5) | |
H4A | −0.1418 | 0.3909 | 0.0583 | 0.026* | |
H4B | −0.1610 | 0.5947 | 0.0564 | 0.026* | |
C5 | 0.0523 (3) | 0.5074 (3) | 0.02397 (8) | 0.0225 (5) | |
C6 | 0.0916 (4) | 0.6620 (4) | 0.00384 (9) | 0.0287 (6) | |
H6A | 0.0361 | 0.7642 | 0.0130 | 0.034* | |
C7 | 0.2115 (4) | 0.6681 (4) | −0.02956 (9) | 0.0379 (7) | |
H7 | 0.2369 | 0.7742 | −0.0433 | 0.045* | |
C8 | 0.2943 (4) | 0.5202 (5) | −0.04293 (10) | 0.0408 (8) | |
H8 | 0.3769 | 0.5249 | −0.0656 | 0.049* | |
C9 | 0.2554 (4) | 0.3642 (4) | −0.02288 (9) | 0.0362 (7) | |
H9 | 0.3115 | 0.2622 | −0.0319 | 0.043* | |
C10 | 0.1343 (3) | 0.3591 (4) | 0.01027 (9) | 0.0285 (6) | |
H10 | 0.1073 | 0.2528 | 0.0237 | 0.034* | |
C11 | 0.2705 (3) | 0.3717 (3) | 0.22407 (8) | 0.0188 (5) | |
C12 | 0.2951 (3) | 0.6740 (3) | 0.22447 (9) | 0.0204 (5) | |
H12A | 0.3267 | 0.7640 | 0.2458 | 0.024* | |
H12B | 0.3122 | 0.7194 | 0.1946 | 0.024* | |
C13 | 0.4024 (3) | 0.5129 (3) | 0.23158 (8) | 0.0182 (5) | |
C14 | 0.4818 (3) | 0.4960 (3) | 0.27747 (8) | 0.0216 (5) | |
H14A | 0.5443 | 0.3858 | 0.2791 | 0.026* | |
H14B | 0.5662 | 0.5891 | 0.2815 | 0.026* | |
C15 | 0.3560 (3) | 0.5029 (3) | 0.31448 (9) | 0.0241 (6) | |
C16 | 0.3167 (4) | 0.6579 (4) | 0.33511 (10) | 0.0349 (7) | |
H16 | 0.3706 | 0.7604 | 0.3256 | 0.042* | |
C17 | 0.2004 (5) | 0.6641 (5) | 0.36911 (11) | 0.0494 (9) | |
H17 | 0.1766 | 0.7703 | 0.3830 | 0.059* | |
C18 | 0.1194 (5) | 0.5180 (6) | 0.38285 (11) | 0.0534 (11) | |
H18 | 0.0387 | 0.5235 | 0.4060 | 0.064* | |
C19 | 0.1543 (4) | 0.3639 (5) | 0.36335 (10) | 0.0480 (9) | |
H19 | 0.0980 | 0.2630 | 0.3731 | 0.058* | |
C20 | 0.2724 (4) | 0.3547 (4) | 0.32920 (9) | 0.0320 (7) | |
H20 | 0.2963 | 0.2473 | 0.3159 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0163 (10) | 0.0155 (10) | 0.0294 (11) | 0.0016 (8) | 0.0017 (9) | 0.0017 (8) |
N2 | 0.0153 (10) | 0.0163 (10) | 0.0309 (11) | 0.0000 (8) | −0.0011 (9) | −0.0006 (9) |
O1 | 0.0170 (8) | 0.0177 (8) | 0.0306 (9) | −0.0003 (6) | 0.0010 (7) | 0.0025 (7) |
O2 | 0.0151 (9) | 0.0163 (8) | 0.0383 (11) | 0.0012 (7) | 0.0008 (7) | 0.0035 (7) |
O3 | 0.0142 (9) | 0.0215 (8) | 0.0254 (8) | −0.0019 (6) | 0.0037 (7) | −0.0010 (7) |
O4 | 0.0185 (9) | 0.0180 (8) | 0.0316 (9) | 0.0009 (6) | 0.0015 (7) | −0.0020 (7) |
O5 | 0.0130 (9) | 0.0146 (8) | 0.0406 (11) | 0.0007 (6) | 0.0026 (7) | −0.0018 (7) |
O6 | 0.0145 (9) | 0.0222 (8) | 0.0266 (9) | 0.0022 (7) | 0.0034 (7) | 0.0020 (7) |
C1 | 0.0163 (11) | 0.0194 (11) | 0.0175 (10) | 0.0011 (9) | 0.0012 (9) | 0.0004 (9) |
C2 | 0.0128 (11) | 0.0185 (12) | 0.0268 (11) | 0.0002 (9) | −0.0004 (9) | −0.0011 (10) |
C3 | 0.0120 (11) | 0.0176 (11) | 0.0245 (11) | 0.0024 (8) | 0.0003 (9) | 0.0005 (8) |
C4 | 0.0160 (13) | 0.0225 (11) | 0.0258 (12) | 0.0015 (9) | −0.0018 (9) | −0.0005 (9) |
C5 | 0.0164 (13) | 0.0300 (13) | 0.0211 (12) | −0.0014 (10) | −0.0051 (9) | 0.0007 (9) |
C6 | 0.0253 (14) | 0.0330 (14) | 0.0279 (13) | −0.0020 (11) | −0.0040 (11) | 0.0018 (11) |
C7 | 0.0398 (19) | 0.0477 (18) | 0.0261 (14) | −0.0124 (14) | −0.0008 (12) | 0.0052 (12) |
C8 | 0.0313 (17) | 0.066 (2) | 0.0247 (14) | −0.0061 (15) | 0.0022 (12) | −0.0020 (13) |
C9 | 0.0298 (16) | 0.0521 (19) | 0.0268 (14) | 0.0093 (14) | −0.0012 (12) | −0.0046 (13) |
C10 | 0.0272 (14) | 0.0335 (15) | 0.0249 (12) | 0.0044 (11) | −0.0021 (10) | 0.0010 (11) |
C11 | 0.0161 (11) | 0.0196 (11) | 0.0206 (10) | 0.0026 (9) | 0.0012 (9) | −0.0004 (9) |
C12 | 0.0131 (12) | 0.0208 (12) | 0.0272 (12) | −0.0017 (9) | 0.0026 (10) | −0.0013 (10) |
C13 | 0.0144 (12) | 0.0186 (11) | 0.0214 (11) | 0.0002 (9) | 0.0019 (9) | −0.0017 (9) |
C14 | 0.0145 (12) | 0.0254 (12) | 0.0248 (12) | −0.0002 (9) | −0.0032 (10) | −0.0020 (9) |
C15 | 0.0190 (14) | 0.0319 (13) | 0.0214 (12) | −0.0009 (10) | −0.0023 (10) | 0.0000 (9) |
C16 | 0.0389 (17) | 0.0381 (16) | 0.0278 (14) | 0.0050 (13) | −0.0017 (12) | −0.0076 (12) |
C17 | 0.048 (2) | 0.070 (2) | 0.0306 (16) | 0.0204 (19) | 0.0006 (15) | −0.0140 (15) |
C18 | 0.035 (2) | 0.100 (3) | 0.0252 (15) | 0.0057 (19) | 0.0082 (14) | 0.0016 (17) |
C19 | 0.0339 (17) | 0.082 (3) | 0.0283 (15) | −0.0180 (17) | −0.0036 (13) | 0.0164 (16) |
C20 | 0.0260 (15) | 0.0431 (17) | 0.0268 (14) | −0.0094 (12) | −0.0053 (11) | 0.0068 (12) |
N1—C1 | 1.317 (3) | C7—C8 | 1.385 (5) |
N1—O2 | 1.404 (3) | C7—H7 | 0.9500 |
N1—H1 | 0.84 (3) | C8—C9 | 1.397 (5) |
N2—C11 | 1.313 (3) | C8—H8 | 0.9500 |
N2—O5 | 1.420 (3) | C9—C10 | 1.390 (4) |
N2—H2 | 0.99 (3) | C9—H9 | 0.9500 |
O1—C1 | 1.252 (3) | C10—H10 | 0.9500 |
O2—C2 | 1.454 (3) | C11—C13 | 1.527 (3) |
O3—C3 | 1.407 (3) | C12—C13 | 1.527 (3) |
O3—H3 | 0.84 (4) | C12—H12A | 0.9900 |
O4—C11 | 1.251 (3) | C12—H12B | 0.9900 |
O5—C12 | 1.456 (3) | C13—C14 | 1.543 (3) |
O6—C13 | 1.417 (3) | C14—C15 | 1.503 (4) |
O6—H6 | 0.90 (4) | C14—H14A | 0.9900 |
C1—C3 | 1.536 (3) | C14—H14B | 0.9900 |
C2—C3 | 1.531 (3) | C15—C16 | 1.399 (4) |
C2—H2A | 0.9900 | C15—C20 | 1.403 (4) |
C2—H2B | 0.9900 | C16—C17 | 1.384 (5) |
C3—C4 | 1.547 (3) | C16—H16 | 0.9500 |
C4—C5 | 1.516 (4) | C17—C18 | 1.371 (6) |
C4—H4A | 0.9900 | C17—H17 | 0.9500 |
C4—H4B | 0.9900 | C18—C19 | 1.369 (6) |
C5—C10 | 1.388 (4) | C18—H18 | 0.9500 |
C5—C6 | 1.389 (4) | C19—C20 | 1.399 (4) |
C6—C7 | 1.390 (4) | C19—H19 | 0.9500 |
C6—H6A | 0.9500 | C20—H20 | 0.9500 |
C1—N1—O2 | 114.3 (2) | C10—C9—H9 | 120.2 |
C1—N1—H1 | 126 (2) | C8—C9—H9 | 120.2 |
O2—N1—H1 | 119 (2) | C5—C10—C9 | 120.8 (3) |
C11—N2—O5 | 113.8 (2) | C5—C10—H10 | 119.6 |
C11—N2—H2 | 130.3 (17) | C9—C10—H10 | 119.6 |
O5—N2—H2 | 115.8 (17) | O4—C11—N2 | 124.6 (2) |
N1—O2—C2 | 104.74 (16) | O4—C11—C13 | 126.9 (2) |
C3—O3—H3 | 112 (2) | N2—C11—C13 | 108.5 (2) |
N2—O5—C12 | 104.81 (16) | O5—C12—C13 | 105.69 (19) |
C13—O6—H6 | 109 (2) | O5—C12—H12A | 110.6 |
O1—C1—N1 | 125.4 (2) | C13—C12—H12A | 110.6 |
O1—C1—C3 | 126.3 (2) | O5—C12—H12B | 110.6 |
N1—C1—C3 | 108.3 (2) | C13—C12—H12B | 110.6 |
O2—C2—C3 | 106.16 (19) | H12A—C12—H12B | 108.7 |
O2—C2—H2A | 110.5 | O6—C13—C12 | 108.02 (19) |
C3—C2—H2A | 110.5 | O6—C13—C11 | 110.79 (18) |
O2—C2—H2B | 110.5 | C12—C13—C11 | 101.6 (2) |
C3—C2—H2B | 110.5 | O6—C13—C14 | 110.8 (2) |
H2A—C2—H2B | 108.7 | C12—C13—C14 | 115.0 (2) |
O3—C3—C2 | 107.97 (19) | C11—C13—C14 | 110.4 (2) |
O3—C3—C1 | 111.08 (18) | C15—C14—C13 | 114.8 (2) |
C2—C3—C1 | 100.72 (19) | C15—C14—H14A | 108.6 |
O3—C3—C4 | 111.3 (2) | C13—C14—H14A | 108.6 |
C2—C3—C4 | 115.0 (2) | C15—C14—H14B | 108.6 |
C1—C3—C4 | 110.30 (19) | C13—C14—H14B | 108.6 |
C5—C4—C3 | 114.2 (2) | H14A—C14—H14B | 107.5 |
C5—C4—H4A | 108.7 | C16—C15—C20 | 117.7 (3) |
C3—C4—H4A | 108.7 | C16—C15—C14 | 121.1 (2) |
C5—C4—H4B | 108.7 | C20—C15—C14 | 121.2 (2) |
C3—C4—H4B | 108.7 | C17—C16—C15 | 121.0 (3) |
H4A—C4—H4B | 107.6 | C17—C16—H16 | 119.5 |
C10—C5—C6 | 119.2 (3) | C15—C16—H16 | 119.5 |
C10—C5—C4 | 120.3 (2) | C18—C17—C16 | 120.4 (3) |
C6—C5—C4 | 120.6 (2) | C18—C17—H17 | 119.8 |
C5—C6—C7 | 120.4 (3) | C16—C17—H17 | 119.8 |
C5—C6—H6A | 119.8 | C19—C18—C17 | 120.2 (3) |
C7—C6—H6A | 119.8 | C19—C18—H18 | 119.9 |
C8—C7—C6 | 120.4 (3) | C17—C18—H18 | 119.9 |
C8—C7—H7 | 119.8 | C18—C19—C20 | 120.3 (3) |
C6—C7—H7 | 119.8 | C18—C19—H19 | 119.9 |
C7—C8—C9 | 119.6 (3) | C20—C19—H19 | 119.9 |
C7—C8—H8 | 120.2 | C19—C20—C15 | 120.4 (3) |
C9—C8—H8 | 120.2 | C19—C20—H20 | 119.8 |
C10—C9—C8 | 119.7 (3) | C15—C20—H20 | 119.8 |
C1—N1—O2—C2 | 18.2 (3) | C8—C9—C10—C5 | −0.5 (4) |
C11—N2—O5—C12 | 17.9 (3) | O5—N2—C11—O4 | 176.1 (2) |
O2—N1—C1—O1 | 176.6 (2) | O5—N2—C11—C13 | −3.9 (3) |
O2—N1—C1—C3 | −4.2 (3) | N2—O5—C12—C13 | −23.6 (2) |
N1—O2—C2—C3 | −24.0 (2) | O5—C12—C13—O6 | 137.6 (2) |
O2—C2—C3—O3 | 137.52 (19) | O5—C12—C13—C11 | 21.0 (2) |
O2—C2—C3—C1 | 21.0 (2) | O5—C12—C13—C14 | −98.2 (2) |
O2—C2—C3—C4 | −97.5 (2) | O4—C11—C13—O6 | 54.6 (3) |
O1—C1—C3—O3 | 54.3 (3) | N2—C11—C13—O6 | −125.4 (2) |
N1—C1—C3—O3 | −124.9 (2) | O4—C11—C13—C12 | 169.2 (2) |
O1—C1—C3—C2 | 168.5 (2) | N2—C11—C13—C12 | −10.9 (3) |
N1—C1—C3—C2 | −10.7 (3) | O4—C11—C13—C14 | −68.4 (3) |
O1—C1—C3—C4 | −69.6 (3) | N2—C11—C13—C14 | 111.5 (2) |
N1—C1—C3—C4 | 111.2 (2) | O6—C13—C14—C15 | 178.80 (19) |
O3—C3—C4—C5 | 179.33 (18) | C12—C13—C14—C15 | 56.0 (3) |
C2—C3—C4—C5 | 56.1 (3) | C11—C13—C14—C15 | −58.1 (3) |
C1—C3—C4—C5 | −56.9 (3) | C13—C14—C15—C16 | −92.4 (3) |
C3—C4—C5—C10 | 86.2 (3) | C13—C14—C15—C20 | 86.9 (3) |
C3—C4—C5—C6 | −93.7 (3) | C20—C15—C16—C17 | 0.5 (4) |
C10—C5—C6—C7 | −0.1 (4) | C14—C15—C16—C17 | 179.8 (3) |
C4—C5—C6—C7 | 179.9 (2) | C15—C16—C17—C18 | −0.9 (5) |
C5—C6—C7—C8 | −0.5 (4) | C16—C17—C18—C19 | 0.8 (5) |
C6—C7—C8—C9 | 0.5 (5) | C17—C18—C19—C20 | −0.2 (5) |
C7—C8—C9—C10 | 0.0 (5) | C18—C19—C20—C15 | −0.2 (5) |
C6—C5—C10—C9 | 0.6 (4) | C16—C15—C20—C19 | 0.0 (4) |
C4—C5—C10—C9 | −179.4 (2) | C14—C15—C20—C19 | −179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.84 (3) | 1.94 (3) | 2.786 (3) | 176 (3) |
O3—H3···O1ii | 0.84 (4) | 1.97 (4) | 2.813 (3) | 177 (3) |
N2—H2···O4ii | 0.99 (3) | 1.80 (3) | 2.784 (3) | 170 (3) |
O6—H6···O4i | 0.90 (4) | 1.92 (4) | 2.805 (3) | 166 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z. |