Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040335/fb2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040335/fb2026Isup2.hkl |
CCDC reference: 627649
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.190
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.825 0.989 Tmin(prime) and Tmax expected: 0.966 0.989 RR(prime) = 0.854 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C12H11NO3 | F(000) = 456 |
Mr = 217.22 | Dx = 1.340 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2085 reflections |
a = 7.6525 (2) Å | θ = 3.0–20.1° |
b = 19.2946 (6) Å | µ = 0.10 mm−1 |
c = 8.0851 (2) Å | T = 293 K |
β = 115.547 (1)° | Block, colourless |
V = 1077.07 (5) Å3 | 0.35 × 0.20 × 0.11 mm |
Z = 4 |
Bruker SMART APEX2 CCD area-detector diffractometer | 3127 independent reflections |
Radiation source: fine-focus sealed tube | 1382 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −26→24 |
Tmin = 0.825, Tmax = 0.989 | l = −11→11 |
15320 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.085P)2 + 0.0079P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3127 reflections | Δρmax = 0.26 e Å−3 |
147 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
32 constraints | Extinction coefficient: 0.015 (4) |
Primary atom site location: structure-invariant direct methods |
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 | 0.2450 (3) | 0.47693 (8) | 0.2538 (2) | 0.0897 (6) | |
O2 | 0.1983 (2) | 0.37585 (7) | 0.10656 (18) | 0.0658 (5) | |
O3 | 0.3619 (3) | 0.66176 (9) | 0.3035 (2) | 0.1126 (7) | |
N1 | 0.2327 (2) | 0.47077 (8) | −0.0330 (2) | 0.0591 (5) | |
C1 | 0.1961 (3) | 0.43126 (12) | −0.1902 (3) | 0.0716 (6) | |
H1 | 0.1696 | 0.3840 | −0.2016 | 0.086* | |
C2 | 0.2049 (3) | 0.47122 (12) | −0.3205 (3) | 0.0729 (7) | |
H2 | 0.1853 | 0.4568 | −0.4370 | 0.087* | |
C3 | 0.2494 (3) | 0.53974 (11) | −0.2506 (2) | 0.0593 (6) | |
C4 | 0.2766 (3) | 0.60073 (13) | −0.3289 (3) | 0.0730 (7) | |
H4 | 0.2676 | 0.6006 | −0.4474 | 0.088* | |
C5 | 0.3164 (3) | 0.66041 (13) | −0.2298 (3) | 0.0773 (7) | |
H5 | 0.3310 | 0.7016 | −0.2822 | 0.093* | |
C6 | 0.3354 (3) | 0.66021 (12) | −0.0525 (3) | 0.0707 (6) | |
H6 | 0.3652 | 0.7017 | 0.0125 | 0.085* | |
C7 | 0.3122 (3) | 0.60097 (10) | 0.0340 (3) | 0.0583 (5) | |
C8 | 0.2682 (3) | 0.53959 (10) | −0.0690 (2) | 0.0538 (5) | |
C9 | 0.2262 (3) | 0.44345 (11) | 0.1230 (3) | 0.0553 (5) | |
C10 | 0.1960 (4) | 0.34024 (11) | 0.2639 (3) | 0.0756 (7) | |
H10A | 0.0925 | 0.3581 | 0.2908 | 0.091* | |
H10B | 0.3181 | 0.3469 | 0.3709 | 0.091* | |
C11 | 0.1645 (5) | 0.26536 (12) | 0.2158 (4) | 0.1008 (9) | |
H11A | 0.1613 | 0.2400 | 0.3166 | 0.151* | |
H11B | 0.2682 | 0.2483 | 0.1903 | 0.151* | |
H11C | 0.0436 | 0.2595 | 0.1094 | 0.151* | |
C12 | 0.3466 (5) | 0.61013 (14) | 0.2252 (3) | 0.1060 (10) | |
H12 | 0.3576 | 0.5698 | 0.2919 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1491 (16) | 0.0700 (10) | 0.0777 (10) | −0.0145 (9) | 0.0750 (11) | −0.0121 (8) |
O2 | 0.0863 (10) | 0.0531 (9) | 0.0610 (9) | 0.0003 (7) | 0.0346 (8) | 0.0045 (7) |
O3 | 0.191 (2) | 0.0737 (12) | 0.0784 (11) | −0.0082 (12) | 0.0629 (13) | −0.0191 (10) |
N1 | 0.0831 (12) | 0.0497 (10) | 0.0441 (8) | 0.0035 (8) | 0.0270 (8) | −0.0013 (7) |
C1 | 0.0984 (17) | 0.0564 (13) | 0.0537 (12) | 0.0067 (11) | 0.0270 (11) | −0.0089 (10) |
C2 | 0.0962 (16) | 0.0749 (16) | 0.0464 (11) | 0.0173 (12) | 0.0295 (11) | −0.0038 (11) |
C3 | 0.0656 (12) | 0.0686 (14) | 0.0456 (10) | 0.0101 (10) | 0.0259 (9) | 0.0042 (10) |
C4 | 0.0839 (15) | 0.0879 (18) | 0.0548 (12) | 0.0029 (12) | 0.0370 (11) | 0.0123 (12) |
C5 | 0.0932 (17) | 0.0739 (16) | 0.0731 (15) | −0.0060 (12) | 0.0436 (13) | 0.0146 (13) |
C6 | 0.0813 (15) | 0.0627 (14) | 0.0680 (13) | −0.0073 (11) | 0.0322 (11) | 0.0017 (11) |
C7 | 0.0697 (13) | 0.0556 (12) | 0.0537 (11) | −0.0032 (9) | 0.0303 (10) | −0.0012 (9) |
C8 | 0.0609 (11) | 0.0545 (12) | 0.0481 (10) | 0.0045 (9) | 0.0255 (9) | 0.0025 (9) |
C9 | 0.0606 (12) | 0.0543 (13) | 0.0538 (11) | 0.0010 (9) | 0.0271 (9) | −0.0007 (9) |
C10 | 0.0987 (17) | 0.0681 (15) | 0.0685 (14) | 0.0007 (12) | 0.0440 (13) | 0.0098 (11) |
C11 | 0.155 (3) | 0.0605 (15) | 0.110 (2) | 0.0024 (16) | 0.079 (2) | 0.0120 (15) |
C12 | 0.197 (3) | 0.0633 (16) | 0.0731 (16) | −0.0381 (17) | 0.0723 (19) | −0.0195 (13) |
O1—C9 | 1.193 (2) | C4—H4 | 0.93 |
O2—C9 | 1.319 (2) | C5—C6 | 1.377 (3) |
O2—C10 | 1.453 (2) | C5—H5 | 0.93 |
O3—C12 | 1.159 (3) | C6—C7 | 1.391 (3) |
N1—C9 | 1.388 (2) | C6—H6 | 0.93 |
N1—C1 | 1.403 (2) | C7—C8 | 1.403 (3) |
N1—C8 | 1.411 (2) | C7—C12 | 1.463 (3) |
C1—C2 | 1.331 (3) | C10—C11 | 1.489 (3) |
C1—H1 | 0.93 | C10—H10A | 0.97 |
C2—C3 | 1.420 (3) | C10—H10B | 0.97 |
C2—H2 | 0.93 | C11—H11A | 0.96 |
C3—C4 | 1.394 (3) | C11—H11B | 0.96 |
C3—C8 | 1.412 (3) | C11—H11C | 0.96 |
C4—C5 | 1.360 (3) | C12—H12 | 0.93 |
C9—O2—C10 | 116.22 (15) | C6—C7—C12 | 115.36 (19) |
C9—N1—C1 | 123.07 (17) | C8—C7—C12 | 128.13 (19) |
C9—N1—C8 | 129.12 (16) | C7—C8—N1 | 133.64 (17) |
C1—N1—C8 | 107.78 (16) | C7—C8—C3 | 120.43 (18) |
C2—C1—N1 | 110.13 (19) | N1—C8—C3 | 105.92 (16) |
C2—C1—H1 | 124.9 | O1—C9—O2 | 125.23 (18) |
N1—C1—H1 | 124.9 | O1—C9—N1 | 124.18 (19) |
C1—C2—C3 | 108.04 (18) | O2—C9—N1 | 110.59 (16) |
C1—C2—H2 | 126.0 | O2—C10—C11 | 106.95 (18) |
C3—C2—H2 | 126.0 | O2—C10—H10A | 110.3 |
C4—C3—C8 | 120.39 (19) | C11—C10—H10A | 110.3 |
C4—C3—C2 | 131.5 (2) | O2—C10—H10B | 110.3 |
C8—C3—C2 | 108.12 (18) | C11—C10—H10B | 110.3 |
C5—C4—C3 | 119.1 (2) | H10A—C10—H10B | 108.6 |
C5—C4—H4 | 120.4 | C10—C11—H11A | 109.5 |
C3—C4—H4 | 120.4 | C10—C11—H11B | 109.5 |
C4—C5—C6 | 120.5 (2) | H11A—C11—H11B | 109.5 |
C4—C5—H5 | 119.8 | C10—C11—H11C | 109.5 |
C6—C5—H5 | 119.8 | H11A—C11—H11C | 109.5 |
C5—C6—C7 | 123.1 (2) | H11B—C11—H11C | 109.5 |
C5—C6—H6 | 118.4 | O3—C12—C7 | 127.7 (2) |
C7—C6—H6 | 118.4 | O3—C12—H12 | 116.2 |
C6—C7—C8 | 116.43 (19) | C7—C12—H12 | 116.2 |
C9—N1—C1—C2 | 177.58 (18) | C1—N1—C8—C7 | −180.0 (2) |
C8—N1—C1—C2 | −0.6 (2) | C9—N1—C8—C3 | −177.36 (17) |
N1—C1—C2—C3 | 0.3 (3) | C1—N1—C8—C3 | 0.7 (2) |
C1—C2—C3—C4 | 179.4 (2) | C4—C3—C8—C7 | 0.7 (3) |
C1—C2—C3—C8 | 0.2 (3) | C2—C3—C8—C7 | −179.97 (18) |
C8—C3—C4—C5 | −1.7 (3) | C4—C3—C8—N1 | −179.84 (17) |
C2—C3—C4—C5 | 179.2 (2) | C2—C3—C8—N1 | −0.5 (2) |
C3—C4—C5—C6 | 1.9 (3) | C10—O2—C9—O1 | −1.7 (3) |
C4—C5—C6—C7 | −1.3 (4) | C10—O2—C9—N1 | 177.72 (16) |
C5—C6—C7—C8 | 0.3 (3) | C1—N1—C9—O1 | −175.20 (19) |
C5—C6—C7—C12 | 177.3 (2) | C8—N1—C9—O1 | 2.6 (3) |
C6—C7—C8—N1 | −179.3 (2) | C1—N1—C9—O2 | 5.4 (3) |
C12—C7—C8—N1 | 4.1 (4) | C8—N1—C9—O2 | −176.85 (17) |
C6—C7—C8—C3 | 0.0 (3) | C9—O2—C10—C11 | −179.5 (2) |
C12—C7—C8—C3 | −176.6 (2) | C6—C7—C12—O3 | 12.6 (5) |
C9—N1—C8—C7 | 2.0 (4) | C8—C7—C12—O3 | −170.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3 | 0.93 | 2.49 | 2.797 (3) | 100 |
C12—H12···O1 | 0.93 | 1.95 | 2.724 (3) | 139 |
C10—H10A···Cg1i | 0.97 | 2.78 | 3.632 (3) | 146 |
Symmetry code: (i) −x, −y+1, −z. |
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