Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013407/cv2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013407/cv2019Isup2.hkl |
CCDC reference: 608406
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C17H19NO4 | F(000) = 640 |
Mr = 301.33 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/n | Melting point: 353 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.036 (4) Å | Cell parameters from 25 reflections |
b = 8.5608 (15) Å | θ = 10–12° |
c = 22.180 (7) Å | µ = 0.09 mm−1 |
β = 91.05 (3)° | T = 293 K |
V = 1525.5 (9) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.30 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1866 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
ω–2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.973, Tmax = 0.982 | l = −26→26 |
2881 measured reflections | 2 standard reflections every 60 min |
2676 independent reflections | intensity decay: none |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.095P)2 + 0.4568P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2676 reflections | Δρmax = 0.36 e Å−3 |
200 parameters | Δρmin = −0.27 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: 0.008 (2) |
Experimental. Absorption correction details: number of psi-scan sets used was 3, theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 6.5699 (0.0076) x - 1.2641 (0.0136) y + 12.6750 (0.0270) z = 7.6687 (0.0270) * 0.0114 (0.0016) C61 * -0.0019 (0.0017) O62 * -0.0088 (0.0021) C63 * 0.0147 (0.0021) C64 * -0.0155 (0.0017) C65 - 0.0157 (0.0042) C6 Rms deviation of fitted atoms = 0.0115 - 6.9825 (0.0067) x + 2.3474 (0.0109) y + 9.4913 (0.0274) z = 8.8709 (0.0276) Angle to previous plane (with approximate e.s.d.) = 25.94 (0.14) * -0.0046 (0.0014) C21 * 0.0071 (0.0014) O22 * -0.0071 (0.0017) C23 * 0.0041 (0.0017) C24 * 0.0004 (0.0016) C25 - 0.0313 (0.0038) C2 Rms deviation of fitted atoms = 0.0053 1.3488 (0.0083) x - 7.2705 (0.0075) y + 11.0315 (0.0250) z = 6.6018 (0.0234) Angle to previous plane (with approximate e.s.d.) = 80.07 (0.10) * -0.0104 (0.0011) C2 * 0.0104 (0.0011) C3 * -0.0105 (0.0011) C5 * 0.0105 (0.0011) C6 - 0.5646 (0.0026) N1 0.6087 (0.0031) C4 Rms deviation of fitted atoms = 0.0105 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 | 0.5520 (2) | 0.3051 (2) | 0.14369 (8) | 0.0688 (7) | |
O4 | 0.9429 (2) | 0.89106 (18) | 0.19819 (8) | 0.0686 (7) | |
O22 | 0.7862 (2) | 0.5678 (2) | 0.01420 (7) | 0.0683 (6) | |
O62 | 0.5474 (3) | 0.8580 (2) | 0.14634 (10) | 0.0842 (8) | |
N1 | 0.7578 (2) | 0.48403 (19) | 0.14229 (8) | 0.0460 (6) | |
C1 | 0.6939 (3) | 0.3393 (2) | 0.12944 (10) | 0.0515 (7) | |
C2 | 0.9098 (3) | 0.5463 (2) | 0.11449 (9) | 0.0475 (7) | |
C3 | 1.0172 (3) | 0.6390 (3) | 0.16055 (10) | 0.0504 (7) | |
C4 | 0.9096 (3) | 0.7526 (3) | 0.19437 (10) | 0.0510 (7) | |
C5 | 0.7591 (3) | 0.6821 (3) | 0.22242 (10) | 0.0534 (7) | |
C6 | 0.6524 (3) | 0.5941 (2) | 0.17555 (9) | 0.0474 (7) | |
C11 | 0.8048 (4) | 0.2215 (3) | 0.10041 (13) | 0.0736 (10) | |
C21 | 0.8714 (3) | 0.6420 (3) | 0.05976 (10) | 0.0502 (7) | |
C23 | 0.7597 (4) | 0.6762 (4) | −0.03060 (13) | 0.0799 (13) | |
C24 | 0.8281 (4) | 0.8110 (4) | −0.01475 (14) | 0.0806 (11) | |
C25 | 0.9008 (3) | 0.7909 (3) | 0.04404 (12) | 0.0651 (9) | |
C31 | 1.1125 (3) | 0.5303 (3) | 0.20426 (11) | 0.0598 (8) | |
C32 | 1.2161 (3) | 0.6179 (4) | 0.25053 (13) | 0.0735 (10) | |
C61 | 0.5567 (3) | 0.7029 (2) | 0.13466 (10) | 0.0494 (7) | |
C63 | 0.4479 (4) | 0.9212 (4) | 0.10166 (17) | 0.0913 (14) | |
C64 | 0.4010 (4) | 0.8147 (5) | 0.06484 (14) | 0.0948 (13) | |
C65 | 0.4673 (3) | 0.6663 (3) | 0.08677 (13) | 0.0683 (9) | |
H2 | 0.97590 | 0.45657 | 0.10153 | 0.0570* | |
H3 | 1.09914 | 0.69939 | 0.13812 | 0.0605* | |
H5A | 0.79389 | 0.61057 | 0.25415 | 0.0641* | |
H5B | 0.69313 | 0.76398 | 0.24047 | 0.0641* | |
H6 | 0.57098 | 0.53203 | 0.19758 | 0.0569* | |
H11A | 0.83923 | 0.26013 | 0.06197 | 0.1105* | |
H11B | 0.90096 | 0.20369 | 0.12579 | 0.1105* | |
H11C | 0.74515 | 0.12523 | 0.09486 | 0.1105* | |
H23 | 0.70226 | 0.65771 | −0.06668 | 0.0957* | |
H24 | 0.82887 | 0.90198 | −0.03764 | 0.0966* | |
H25 | 0.95713 | 0.86586 | 0.06686 | 0.0781* | |
H31A | 1.18465 | 0.46276 | 0.18130 | 0.0718* | |
H31B | 1.03337 | 0.46463 | 0.22490 | 0.0718* | |
H32A | 1.27279 | 0.54469 | 0.27649 | 0.1102* | |
H32B | 1.29641 | 0.68150 | 0.23045 | 0.1102* | |
H32C | 1.14517 | 0.68315 | 0.27410 | 0.1102* | |
H63 | 0.41906 | 1.02618 | 0.09865 | 0.1094* | |
H64 | 0.33600 | 0.82915 | 0.03017 | 0.1138* | |
H65 | 0.44988 | 0.56749 | 0.07039 | 0.0820* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0690 (12) | 0.0531 (10) | 0.0846 (12) | −0.0196 (8) | 0.0085 (9) | −0.0077 (9) |
O4 | 0.0694 (11) | 0.0429 (10) | 0.0930 (13) | −0.0047 (8) | −0.0102 (9) | −0.0119 (9) |
O22 | 0.0740 (11) | 0.0725 (11) | 0.0582 (10) | −0.0048 (9) | −0.0007 (8) | −0.0028 (9) |
O62 | 0.0835 (14) | 0.0554 (11) | 0.1130 (16) | 0.0072 (9) | −0.0142 (12) | −0.0084 (10) |
N1 | 0.0483 (10) | 0.0340 (9) | 0.0558 (10) | −0.0019 (7) | 0.0060 (8) | −0.0022 (8) |
C1 | 0.0630 (14) | 0.0377 (11) | 0.0536 (12) | −0.0060 (10) | −0.0001 (10) | 0.0010 (9) |
C2 | 0.0453 (11) | 0.0403 (11) | 0.0572 (12) | 0.0017 (9) | 0.0082 (9) | −0.0026 (9) |
C3 | 0.0458 (11) | 0.0426 (11) | 0.0629 (13) | −0.0015 (9) | 0.0012 (10) | 0.0011 (10) |
C4 | 0.0503 (12) | 0.0439 (12) | 0.0582 (13) | 0.0021 (10) | −0.0113 (10) | −0.0043 (10) |
C5 | 0.0584 (13) | 0.0488 (12) | 0.0531 (12) | 0.0071 (10) | 0.0007 (10) | −0.0079 (10) |
C6 | 0.0472 (11) | 0.0410 (11) | 0.0542 (12) | −0.0011 (9) | 0.0073 (9) | −0.0030 (9) |
C11 | 0.091 (2) | 0.0410 (13) | 0.0891 (19) | −0.0030 (13) | 0.0131 (15) | −0.0126 (13) |
C21 | 0.0445 (11) | 0.0522 (12) | 0.0542 (12) | −0.0001 (10) | 0.0068 (9) | −0.0018 (10) |
C23 | 0.0703 (18) | 0.112 (3) | 0.0574 (15) | 0.0072 (17) | 0.0028 (13) | 0.0150 (16) |
C24 | 0.0719 (18) | 0.086 (2) | 0.0842 (19) | 0.0106 (16) | 0.0129 (15) | 0.0324 (17) |
C25 | 0.0597 (14) | 0.0575 (15) | 0.0783 (17) | −0.0018 (12) | 0.0079 (12) | 0.0137 (13) |
C31 | 0.0515 (13) | 0.0555 (14) | 0.0724 (15) | 0.0099 (11) | −0.0004 (11) | 0.0021 (12) |
C32 | 0.0538 (15) | 0.0861 (19) | 0.0800 (17) | 0.0134 (13) | −0.0114 (13) | −0.0036 (15) |
C61 | 0.0437 (11) | 0.0394 (11) | 0.0653 (14) | −0.0005 (9) | 0.0086 (10) | −0.0034 (10) |
C63 | 0.078 (2) | 0.071 (2) | 0.124 (3) | 0.0185 (16) | −0.0187 (19) | 0.0262 (19) |
C64 | 0.0636 (17) | 0.149 (3) | 0.0712 (18) | 0.021 (2) | −0.0157 (14) | 0.002 (2) |
C65 | 0.0541 (14) | 0.0679 (16) | 0.0822 (17) | 0.0053 (12) | −0.0187 (12) | −0.0299 (14) |
O1—C1 | 1.224 (3) | C63—C64 | 1.276 (5) |
O4—C4 | 1.218 (3) | C64—C65 | 1.458 (5) |
O22—C21 | 1.367 (3) | C2—H2 | 0.9800 |
O22—C23 | 1.373 (4) | C3—H3 | 0.9800 |
O62—C61 | 1.355 (3) | C5—H5A | 0.9700 |
O62—C63 | 1.373 (4) | C5—H5B | 0.9700 |
N1—C1 | 1.369 (3) | C6—H6 | 0.9800 |
N1—C2 | 1.478 (3) | C11—H11A | 0.9600 |
N1—C6 | 1.474 (3) | C11—H11B | 0.9600 |
C1—C11 | 1.499 (4) | C11—H11C | 0.9600 |
C2—C3 | 1.545 (3) | C23—H23 | 0.9300 |
C2—C21 | 1.492 (3) | C24—H24 | 0.9300 |
C3—C4 | 1.510 (4) | C25—H25 | 0.9300 |
C3—C31 | 1.538 (4) | C31—H31A | 0.9700 |
C4—C5 | 1.497 (3) | C31—H31B | 0.9700 |
C5—C6 | 1.533 (3) | C32—H32A | 0.9600 |
C6—C61 | 1.502 (3) | C32—H32B | 0.9600 |
C21—C25 | 1.344 (4) | C32—H32C | 0.9600 |
C23—C24 | 1.323 (5) | C63—H63 | 0.9300 |
C24—C25 | 1.429 (4) | C64—H64 | 0.9300 |
C31—C32 | 1.509 (4) | C65—H65 | 0.9300 |
C61—C65 | 1.309 (4) | ||
O1···C61 | 3.412 (3) | C24···H11Avi | 2.9500 |
O1···C65 | 3.404 (4) | C24···H63vii | 3.0400 |
O4···C6i | 3.395 (3) | C25···H3 | 2.7200 |
O4···C32 | 3.397 (4) | C31···H5A | 2.8900 |
O22···C1 | 3.314 (3) | C61···H32Bviii | 3.0100 |
O22···N1 | 2.943 (3) | C63···H24vii | 3.0200 |
O22···C65 | 3.166 (3) | C63···H11Cix | 2.9700 |
O62···C4 | 3.211 (4) | H2···C11 | 2.4400 |
O1···H63ii | 2.7900 | H2···H11A | 2.1800 |
O1···H65 | 2.8800 | H2···H11B | 2.3100 |
O1···H32Ciii | 2.6500 | H2···H31A | 2.4200 |
O1···H6 | 2.2800 | H2···C23vi | 2.9000 |
O1···H23iv | 2.6600 | H3···C25 | 2.7200 |
O4···H5Ai | 2.8900 | H3···H25 | 2.4000 |
O4···H32Av | 2.6900 | H3···H32B | 2.5700 |
O4···H6i | 2.6100 | H5A···C31 | 2.8900 |
O22···H11A | 2.8700 | H5A···H31B | 2.3900 |
O22···H65iv | 2.8900 | H5A···O4iii | 2.8900 |
O62···H5B | 2.5100 | H5B···O62 | 2.5100 |
N1···O22 | 2.943 (3) | H5B···C1i | 3.0800 |
N1···H31B | 2.8500 | H6···O1 | 2.2800 |
C1···O22 | 3.314 (3) | H6···O4iii | 2.6100 |
C1···C65 | 3.462 (4) | H11A···O22 | 2.8700 |
C1···C5iii | 3.564 (4) | H11A···C2 | 2.7700 |
C4···C25 | 3.350 (4) | H11A···H2 | 2.1800 |
C4···O62 | 3.211 (4) | H11A···C24vi | 2.9500 |
C5···C1i | 3.564 (4) | H11A···H64iv | 2.5800 |
C6···O4iii | 3.395 (3) | H11B···C2 | 2.9400 |
C11···C24vi | 3.549 (5) | H11B···H2 | 2.3100 |
C21···C65 | 3.320 (4) | H11C···C63ii | 2.9700 |
C21···C61 | 3.095 (4) | H23···O1iv | 2.6600 |
C23···C65 | 3.540 (4) | H23···H65iv | 2.2800 |
C24···C11vi | 3.549 (5) | H24···C63vii | 3.0200 |
C25···C61 | 3.530 (4) | H24···H63vii | 2.4700 |
C25···C4 | 3.350 (4) | H25···C3 | 2.8800 |
C32···O4 | 3.397 (4) | H25···C4 | 3.0200 |
C61···C25 | 3.530 (4) | H25···H3 | 2.4000 |
C61···O1 | 3.412 (3) | H31A···H2 | 2.4200 |
C61···C21 | 3.095 (4) | H31B···N1 | 2.8500 |
C65···O1 | 3.404 (4) | H31B···C5 | 2.8800 |
C65···O22 | 3.166 (3) | H31B···H5A | 2.3900 |
C65···C1 | 3.462 (4) | H32A···O4x | 2.6900 |
C65···C23 | 3.540 (4) | H32B···C61xi | 3.0100 |
C65···C21 | 3.320 (4) | H32B···H3 | 2.5700 |
C1···H5Biii | 3.0800 | H32C···C4 | 2.6300 |
C1···H65 | 3.0500 | H32C···O1i | 2.6500 |
C2···H11A | 2.7700 | H63···O1ix | 2.7900 |
C2···H11B | 2.9400 | H63···C24vii | 3.0400 |
C3···H25 | 2.8800 | H63···H24vii | 2.4700 |
C4···H32C | 2.6300 | H64···H11Aiv | 2.5800 |
C4···H25 | 3.0200 | H65···O1 | 2.8800 |
C5···H31B | 2.8800 | H65···C1 | 3.0500 |
C11···H2 | 2.4400 | H65···O22iv | 2.8900 |
C23···H2vi | 2.9000 | H65···C23iv | 2.8100 |
C23···H65iv | 2.8100 | H65···H23iv | 2.2800 |
C21—O22—C23 | 106.9 (2) | C31—C3—H3 | 108.00 |
C61—O62—C63 | 106.4 (2) | C4—C5—H5A | 109.00 |
C1—N1—C2 | 123.32 (17) | C4—C5—H5B | 109.00 |
C1—N1—C6 | 117.77 (17) | C6—C5—H5A | 109.00 |
C2—N1—C6 | 117.72 (15) | C6—C5—H5B | 109.00 |
O1—C1—N1 | 120.67 (19) | H5A—C5—H5B | 108.00 |
O1—C1—C11 | 120.92 (19) | N1—C6—H6 | 107.00 |
N1—C1—C11 | 118.3 (2) | C5—C6—H6 | 107.00 |
N1—C2—C3 | 111.44 (17) | C61—C6—H6 | 107.00 |
N1—C2—C21 | 112.17 (19) | C1—C11—H11A | 109.00 |
C3—C2—C21 | 111.14 (18) | C1—C11—H11B | 109.00 |
C2—C3—C4 | 109.96 (19) | C1—C11—H11C | 109.00 |
C2—C3—C31 | 111.8 (2) | H11A—C11—H11B | 109.00 |
C4—C3—C31 | 111.08 (19) | H11A—C11—H11C | 109.00 |
O4—C4—C3 | 122.3 (2) | H11B—C11—H11C | 109.00 |
O4—C4—C5 | 122.8 (2) | O22—C23—H23 | 125.00 |
C3—C4—C5 | 114.9 (2) | C24—C23—H23 | 125.00 |
C4—C5—C6 | 111.24 (19) | C23—C24—H24 | 126.00 |
N1—C6—C5 | 109.52 (19) | C25—C24—H24 | 126.00 |
N1—C6—C61 | 112.76 (17) | C21—C25—H25 | 127.00 |
C5—C6—C61 | 112.24 (16) | C24—C25—H25 | 127.00 |
O22—C21—C2 | 116.1 (2) | C3—C31—H31A | 109.00 |
O22—C21—C25 | 109.7 (2) | C3—C31—H31B | 109.00 |
C2—C21—C25 | 134.2 (2) | C32—C31—H31A | 109.00 |
O22—C23—C24 | 109.8 (3) | C32—C31—H31B | 109.00 |
C23—C24—C25 | 107.4 (3) | H31A—C31—H31B | 108.00 |
C21—C25—C24 | 106.3 (2) | C31—C32—H32A | 109.00 |
C3—C31—C32 | 113.0 (2) | C31—C32—H32B | 109.00 |
O62—C61—C6 | 121.4 (2) | C31—C32—H32C | 110.00 |
O62—C61—C65 | 111.0 (2) | H32A—C32—H32B | 109.00 |
C6—C61—C65 | 127.49 (19) | H32A—C32—H32C | 109.00 |
O62—C63—C64 | 110.0 (3) | H32B—C32—H32C | 109.00 |
C63—C64—C65 | 107.9 (3) | O62—C63—H63 | 125.00 |
C61—C65—C64 | 104.7 (2) | C64—C63—H63 | 125.00 |
N1—C2—H2 | 107.00 | C63—C64—H64 | 126.00 |
C3—C2—H2 | 107.00 | C65—C64—H64 | 126.00 |
C21—C2—H2 | 107.00 | C61—C65—H65 | 128.00 |
C2—C3—H3 | 108.00 | C64—C65—H65 | 128.00 |
C4—C3—H3 | 108.00 | ||
C21—O22—C23—C24 | 1.4 (3) | N1—C2—C21—C25 | 120.6 (3) |
C23—O22—C21—C25 | −1.2 (3) | N1—C2—C3—C4 | −48.1 (2) |
C23—O22—C21—C2 | 178.3 (2) | C4—C3—C31—C32 | −55.7 (3) |
C63—O62—C61—C65 | −1.3 (3) | C2—C3—C31—C32 | −178.9 (2) |
C61—O62—C63—C64 | −0.8 (4) | C31—C3—C4—C5 | −72.1 (3) |
C63—O62—C61—C6 | −178.3 (2) | C2—C3—C4—C5 | 52.3 (3) |
C6—N1—C1—O1 | 2.1 (3) | C31—C3—C4—O4 | 108.2 (3) |
C1—N1—C6—C61 | −94.9 (2) | C2—C3—C4—O4 | −127.5 (2) |
C2—N1—C1—C11 | 18.0 (3) | O4—C4—C5—C6 | 124.9 (2) |
C1—N1—C6—C5 | 139.38 (19) | C3—C4—C5—C6 | −54.8 (3) |
C1—N1—C2—C21 | 93.6 (2) | C4—C5—C6—N1 | 51.5 (2) |
C6—N1—C2—C3 | 51.7 (2) | C4—C5—C6—C61 | −74.6 (3) |
C2—N1—C1—O1 | −165.1 (2) | C5—C6—C61—O62 | −10.6 (3) |
C2—N1—C6—C5 | −52.7 (2) | N1—C6—C61—O62 | −134.8 (2) |
C6—N1—C2—C21 | −73.6 (2) | N1—C6—C61—C65 | 48.7 (3) |
C1—N1—C2—C3 | −141.0 (2) | C5—C6—C61—C65 | 173.0 (2) |
C2—N1—C6—C61 | 73.1 (2) | C2—C21—C25—C24 | −178.9 (3) |
C6—N1—C1—C11 | −174.8 (2) | O22—C21—C25—C24 | 0.5 (3) |
C21—C2—C3—C31 | −158.3 (2) | O22—C23—C24—C25 | −1.1 (4) |
N1—C2—C3—C31 | 75.8 (2) | C23—C24—C25—C21 | 0.3 (3) |
N1—C2—C21—O22 | −58.7 (2) | C6—C61—C65—C64 | 179.3 (2) |
C21—C2—C3—C4 | 77.9 (2) | O62—C61—C65—C64 | 2.6 (3) |
C3—C2—C21—O22 | 175.77 (19) | O62—C63—C64—C65 | 2.3 (4) |
C3—C2—C21—C25 | −4.9 (4) | C63—C64—C65—C61 | −3.0 (3) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z; (v) −x+5/2, y+1/2, −z+1/2; (vi) −x+2, −y+1, −z; (vii) −x+1, −y+2, −z; (viii) x−1, y, z; (ix) x, y+1, z; (x) −x+5/2, y−1/2, −z+1/2; (xi) x+1, y, z. |