Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026651/at2055sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026651/at2055Isup2.hkl |
CCDC reference: 618111
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C15H14O4 | F(000) = 544 |
Mr = 258.26 | Dx = 1.286 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1992 reflections |
a = 5.3798 (12) Å | θ = 1.8–26.0° |
b = 13.659 (3) Å | µ = 0.09 mm−1 |
c = 18.153 (4) Å | T = 298 K |
V = 1333.9 (5) Å3 | Block, colourless |
Z = 4 | 0.49 × 0.33 × 0.18 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1551 independent reflections |
Radiation source: fine-focus sealed tube | 1234 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −5→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −16→16 |
Tmin = 0.955, Tmax = 0.983 | l = −17→22 |
7462 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.207P] where P = (Fo2 + 2Fc2)/3 |
1551 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.12 e Å−3 |
2 restraints | Δρmin = −0.12 e Å−3 |
Experimental. IR (νmax, cm-1): 1740, 1654, 1578, 1493, 1227 and 953; 1H NMR (CDCl3, δ, p.m.m.): 7.26 (m, 5H, aromatic), 6.90 (dd, J=10 and 5,H-4), 6.80 (dd, J=15 and 1,H-8), 6.20 (dd, J=10, and 2, H-3), 6.16 (dd, J=15 and 6, H-7), 5.26 (dd, J=6 and 3, H-6), 5.15 (dd, J=5 and 3, H-5) and 2.02 (s, 3H,-OMe). 13C NMR (CDCl3, δ, p.m.m.): 170.2 (s, ester carbonyl), 162.6 (s, C-2), 140.8 (d, C-4), 135.7 (d, C-9), 135.0 (d, C-7), 128.8 (d, C-11 dan C-13), 128.7 (d, C-12), 126.9 (d, C-10 and C-14), 125.0 (d, C-8), 121.2 (d, C-3), 79.2 (d, C-6), 64.0 (d, C-5) and 20.7 (q, Ac). |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.1988 (5) | 0.06094 (15) | 0.80970 (11) | 0.0840 (7) | |
O2 | 0.1372 (8) | −0.09214 (18) | 0.77891 (15) | 0.1312 (13) | |
O3 | 0.2487 (4) | 0.18972 (13) | 0.68682 (11) | 0.0684 (6) | |
O4A | 0.469 (2) | 0.3000 (15) | 0.6310 (14) | 0.193 (9) | 0.49 (2) |
O4B | 0.4908 (12) | 0.2341 (10) | 0.5991 (3) | 0.097 (4) | 0.51 (2) |
C2 | 0.2664 (10) | −0.0208 (3) | 0.77337 (19) | 0.0940 (12) | |
C3 | 0.4868 (9) | −0.0148 (3) | 0.72586 (19) | 0.0926 (12) | |
H3A | 0.5674 | −0.0721 | 0.7118 | 0.111* | |
C4 | 0.5721 (8) | 0.0695 (3) | 0.70293 (18) | 0.0838 (10) | |
H4A | 0.7017 | 0.0717 | 0.6690 | 0.101* | |
C5 | 0.4615 (6) | 0.1620 (2) | 0.73118 (15) | 0.0650 (8) | |
H5A | 0.5858 | 0.2144 | 0.7311 | 0.078* | |
C6 | 0.3681 (7) | 0.14439 (19) | 0.80823 (16) | 0.0680 (8) | |
H6A | 0.5114 | 0.1287 | 0.8394 | 0.082* | |
C7 | 0.2879 (6) | 0.2407 (3) | 0.62717 (18) | 0.0792 (10) | |
C8 | 0.0637 (7) | 0.2650 (2) | 0.58597 (16) | 0.0774 (9) | |
H8A | −0.0374 | 0.2075 | 0.5807 | 0.116* | |
H8B | 0.1088 | 0.2891 | 0.5381 | 0.116* | |
H8C | −0.0280 | 0.3145 | 0.6120 | 0.116* | |
C9 | 0.2354 (7) | 0.2285 (2) | 0.84183 (15) | 0.0689 (8) | |
H9A | 0.0928 | 0.2520 | 0.8189 | 0.083* | |
C10 | 0.3111 (7) | 0.2710 (2) | 0.90264 (15) | 0.0667 (8) | |
H10A | 0.4515 | 0.2439 | 0.9244 | 0.080* | |
C11 | 0.2038 (6) | 0.3555 (2) | 0.94070 (14) | 0.0617 (7) | |
C12 | 0.3175 (7) | 0.3910 (2) | 1.00413 (16) | 0.0728 (9) | |
H12A | 0.4606 | 0.3605 | 1.0215 | 0.087* | |
C13 | 0.2237 (8) | 0.4699 (2) | 1.04180 (17) | 0.0823 (10) | |
H13A | 0.3031 | 0.4924 | 1.0840 | 0.099* | |
C14 | 0.0135 (8) | 0.5154 (3) | 1.01708 (19) | 0.0850 (10) | |
H14A | −0.0514 | 0.5687 | 1.0426 | 0.102* | |
C15 | −0.1010 (7) | 0.4823 (2) | 0.95475 (19) | 0.0837 (10) | |
H15A | −0.2430 | 0.5138 | 0.9377 | 0.100* | |
C16 | −0.0087 (7) | 0.4027 (2) | 0.91673 (17) | 0.0728 (9) | |
H16A | −0.0901 | 0.3806 | 0.8747 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1160 (19) | 0.0688 (12) | 0.0671 (12) | −0.0137 (14) | 0.0099 (14) | 0.0117 (10) |
O2 | 0.209 (4) | 0.0731 (15) | 0.1115 (19) | −0.035 (2) | 0.007 (2) | 0.0166 (14) |
O3 | 0.0670 (13) | 0.0739 (12) | 0.0642 (11) | −0.0083 (11) | −0.0064 (11) | 0.0192 (10) |
O4A | 0.101 (6) | 0.226 (14) | 0.253 (17) | −0.064 (8) | −0.074 (8) | 0.174 (13) |
O4B | 0.053 (3) | 0.179 (8) | 0.059 (4) | −0.011 (4) | 0.018 (2) | 0.033 (4) |
C2 | 0.152 (4) | 0.0581 (19) | 0.072 (2) | −0.005 (3) | −0.012 (3) | 0.0162 (17) |
C3 | 0.128 (3) | 0.070 (2) | 0.079 (2) | 0.022 (2) | −0.001 (3) | 0.0025 (18) |
C4 | 0.088 (2) | 0.091 (2) | 0.072 (2) | 0.020 (2) | −0.0027 (19) | 0.0021 (18) |
C5 | 0.068 (2) | 0.0650 (17) | 0.0623 (17) | 0.0010 (16) | −0.0056 (17) | 0.0084 (14) |
C6 | 0.081 (2) | 0.0629 (17) | 0.0598 (17) | 0.0015 (18) | −0.0074 (17) | 0.0068 (14) |
C7 | 0.064 (2) | 0.107 (3) | 0.0669 (19) | −0.007 (2) | 0.0008 (19) | 0.0273 (18) |
C8 | 0.076 (2) | 0.088 (2) | 0.068 (2) | 0.007 (2) | −0.0060 (18) | 0.0095 (17) |
C9 | 0.076 (2) | 0.0732 (17) | 0.0574 (16) | −0.0006 (18) | −0.0056 (17) | 0.0071 (14) |
C10 | 0.076 (2) | 0.0643 (16) | 0.0602 (17) | −0.0003 (17) | −0.0015 (17) | 0.0153 (14) |
C11 | 0.0674 (19) | 0.0642 (16) | 0.0535 (16) | −0.0119 (16) | 0.0021 (15) | 0.0124 (13) |
C12 | 0.079 (2) | 0.0772 (19) | 0.0618 (17) | −0.0095 (18) | −0.0037 (18) | 0.0102 (15) |
C13 | 0.107 (3) | 0.077 (2) | 0.0635 (18) | −0.020 (2) | −0.003 (2) | 0.0005 (16) |
C14 | 0.105 (3) | 0.075 (2) | 0.076 (2) | −0.006 (2) | 0.015 (2) | −0.0010 (18) |
C15 | 0.082 (2) | 0.083 (2) | 0.086 (2) | 0.003 (2) | 0.000 (2) | 0.0089 (19) |
C16 | 0.078 (2) | 0.0740 (19) | 0.0669 (18) | −0.0040 (19) | −0.0051 (18) | 0.0008 (16) |
O1—C2 | 1.347 (4) | C8—H8B | 0.9600 |
O1—C6 | 1.459 (4) | C8—H8C | 0.9600 |
O2—C2 | 1.201 (5) | C9—C10 | 1.312 (4) |
O3—C7 | 1.305 (3) | C9—H9A | 0.9300 |
O3—C5 | 1.450 (3) | C10—C11 | 1.463 (4) |
O4A—C7 | 1.270 (9) | C10—H10A | 0.9300 |
O4B—C7 | 1.209 (6) | C11—C16 | 1.383 (4) |
C2—C3 | 1.469 (6) | C11—C12 | 1.391 (4) |
C3—C4 | 1.308 (5) | C12—C13 | 1.373 (4) |
C3—H3A | 0.9300 | C12—H12A | 0.9300 |
C4—C5 | 1.487 (4) | C13—C14 | 1.366 (5) |
C4—H4A | 0.9300 | C13—H13A | 0.9300 |
C5—C6 | 1.505 (4) | C14—C15 | 1.365 (5) |
C5—H5A | 0.9800 | C14—H14A | 0.9300 |
C6—C9 | 1.484 (4) | C15—C16 | 1.380 (4) |
C6—H6A | 0.9800 | C15—H15A | 0.9300 |
C7—C8 | 1.457 (5) | C16—H16A | 0.9300 |
C8—H8A | 0.9600 | ||
C2—O1—C6 | 118.0 (3) | C7—C8—H8B | 109.5 |
C7—O3—C5 | 118.2 (2) | H8A—C8—H8B | 109.5 |
O2—C2—O1 | 118.4 (4) | C7—C8—H8C | 109.5 |
O2—C2—C3 | 124.2 (4) | H8A—C8—H8C | 109.5 |
O1—C2—C3 | 117.4 (3) | H8B—C8—H8C | 109.5 |
C4—C3—C2 | 121.3 (3) | C10—C9—C6 | 122.6 (3) |
C4—C3—H3A | 119.4 | C10—C9—H9A | 118.7 |
C2—C3—H3A | 119.4 | C6—C9—H9A | 118.7 |
C3—C4—C5 | 119.8 (4) | C9—C10—C11 | 128.6 (3) |
C3—C4—H4A | 120.1 | C9—C10—H10A | 115.7 |
C5—C4—H4A | 120.1 | C11—C10—H10A | 115.7 |
O3—C5—C4 | 110.3 (3) | C16—C11—C12 | 117.5 (3) |
O3—C5—C6 | 107.1 (3) | C16—C11—C10 | 123.0 (3) |
C4—C5—C6 | 108.6 (3) | C12—C11—C10 | 119.5 (3) |
O3—C5—H5A | 110.3 | C13—C12—C11 | 121.6 (3) |
C4—C5—H5A | 110.3 | C13—C12—H12A | 119.2 |
C6—C5—H5A | 110.3 | C11—C12—H12A | 119.2 |
O1—C6—C9 | 107.3 (3) | C14—C13—C12 | 119.9 (3) |
O1—C6—C5 | 110.5 (2) | C14—C13—H13A | 120.1 |
C9—C6—C5 | 114.8 (2) | C12—C13—H13A | 120.1 |
O1—C6—H6A | 108.0 | C15—C14—C13 | 119.7 (4) |
C9—C6—H6A | 108.0 | C15—C14—H14A | 120.2 |
C5—C6—H6A | 108.0 | C13—C14—H14A | 120.2 |
O4B—C7—O4A | 51.5 (10) | C14—C15—C16 | 120.9 (4) |
O4B—C7—O3 | 117.1 (5) | C14—C15—H15A | 119.6 |
O4A—C7—O3 | 114.8 (8) | C16—C15—H15A | 119.6 |
O4B—C7—C8 | 123.2 (4) | C15—C16—C11 | 120.5 (3) |
O4A—C7—C8 | 121.2 (5) | C15—C16—H16A | 119.8 |
O3—C7—C8 | 114.5 (3) | C11—C16—H16A | 119.8 |
C7—C8—H8A | 109.5 | ||
C6—O1—C2—O2 | 174.5 (3) | C5—O3—C7—O4A | −33.3 (15) |
C6—O1—C2—C3 | −9.1 (4) | C5—O3—C7—C8 | 179.9 (3) |
O2—C2—C3—C4 | 157.3 (4) | O1—C6—C9—C10 | 116.9 (3) |
O1—C2—C3—C4 | −18.9 (6) | C5—C6—C9—C10 | −119.9 (3) |
C2—C3—C4—C5 | 6.3 (6) | C6—C9—C10—C11 | 178.2 (3) |
C7—O3—C5—C4 | −85.8 (4) | C9—C10—C11—C16 | 1.8 (5) |
C7—O3—C5—C6 | 156.3 (3) | C9—C10—C11—C12 | −178.4 (3) |
C3—C4—C5—O3 | −87.0 (4) | C16—C11—C12—C13 | −0.1 (4) |
C3—C4—C5—C6 | 30.1 (5) | C10—C11—C12—C13 | −179.9 (3) |
C2—O1—C6—C9 | 171.5 (3) | C11—C12—C13—C14 | 0.1 (5) |
C2—O1—C6—C5 | 45.7 (4) | C12—C13—C14—C15 | −0.4 (5) |
O3—C5—C6—O1 | 64.8 (3) | C13—C14—C15—C16 | 0.7 (5) |
C4—C5—C6—O1 | −54.3 (4) | C14—C15—C16—C11 | −0.7 (5) |
O3—C5—C6—C9 | −56.6 (3) | C12—C11—C16—C15 | 0.4 (4) |
C4—C5—C6—C9 | −175.7 (3) | C10—C11—C16—C15 | −179.8 (3) |
C5—O3—C7—O4B | 24.4 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O4Bi | 0.96 | 2.59 | 3.120 (8) | 115 |
C8—H8B···O4Bii | 0.96 | 2.59 | 3.382 (6) | 140 |
C8—H8C···O2iii | 0.96 | 2.43 | 3.315 (4) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) −x, y+1/2, −z+3/2. |