Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038645/hk2131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038645/hk2131Isup2.hkl |
CCDC reference: 624730
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H19NO4 | F(000) = 808 |
Mr = 385.4 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3059 reflections |
a = 10.0396 (5) Å | θ = 2.3–28.3° |
b = 9.8912 (5) Å | µ = 0.09 mm−1 |
c = 18.9631 (9) Å | T = 100 K |
β = 94.965 (3)° | Block, yellow |
V = 1876.04 (16) Å3 | 0.2 × 0.13 × 0.09 mm |
Z = 4 |
Bruker X8 APEXII 4K diffractometer | 4606 independent reflections |
Graphite monochromator | 3462 reflections with I > 2σ(I) |
Detector resolution: 512 pixels mm-1 | Rint = 0.046 |
φ and ω scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.982, Tmax = 0.992 | k = −12→13 |
13970 measured reflections | l = −25→25 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8797P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.144 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.34 e Å−3 |
4606 reflections | Δρmin = −0.27 e Å−3 |
267 parameters |
Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K diffractometer using an exposure time of 60 s/frame. A total of 901 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 97.9% completeness accomplished. 1H NMR (300 MHz, CDCl3): δ 3.86 (3H, s, CH3), 6.23 (1H, s, CH), 7.00 (2H, d, 3J = 9 Hz, C6H4), 7.49 (6H, m, C6H5), 7.86 (2H, d, 3J = 9 Hz, C6H4), 7.98 (4H, m, C6H5) |
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 | ||
C1 | 0.8626 (2) | −0.0769 (2) | 0.87218 (10) | 0.0320 (5) | |
H1A | 0.9523 | −0.0507 | 0.8606 | 0.048* | |
H1B | 0.8652 | −0.1689 | 0.8913 | 0.048* | |
H1C | 0.8322 | −0.0143 | 0.9075 | 0.048* | |
C2 | 0.7033 (2) | 0.0431 (2) | 0.79677 (9) | 0.0174 (4) | |
C3 | 0.6112 (2) | 0.03525 (19) | 0.73157 (9) | 0.0170 (4) | |
C4 | 0.6122 (2) | −0.0731 (2) | 0.68468 (9) | 0.0182 (4) | |
H4 | 0.6729 | −0.1458 | 0.6944 | 0.022* | |
C5 | 0.5251 (2) | −0.0754 (2) | 0.62396 (9) | 0.0185 (4) | |
H5 | 0.5262 | −0.1496 | 0.5922 | 0.022* | |
C6 | 0.43590 (19) | 0.03071 (19) | 0.60923 (9) | 0.0167 (4) | |
C7 | 0.4309 (2) | 0.1366 (2) | 0.65741 (9) | 0.0202 (4) | |
H7 | 0.3668 | 0.2066 | 0.6491 | 0.024* | |
C8 | 0.5196 (2) | 0.1393 (2) | 0.71743 (9) | 0.0201 (4) | |
H8 | 0.518 | 0.2132 | 0.7494 | 0.024* | |
C9 | 0.2842 (2) | 0.12645 (19) | 0.51204 (9) | 0.0175 (4) | |
C10 | 0.3341 (2) | 0.27011 (19) | 0.52410 (9) | 0.0173 (4) | |
C11 | 0.2415 (2) | 0.37359 (19) | 0.54751 (9) | 0.0174 (4) | |
C12 | 0.1182 (2) | 0.3377 (2) | 0.57072 (10) | 0.0220 (4) | |
H12 | 0.0916 | 0.2456 | 0.5706 | 0.026* | |
C13 | 0.0348 (2) | 0.4364 (2) | 0.59396 (10) | 0.0246 (4) | |
H13 | −0.049 | 0.4119 | 0.6099 | 0.029* | |
C14 | 0.0731 (2) | 0.5703 (2) | 0.59405 (10) | 0.0232 (4) | |
H14 | 0.0155 | 0.6379 | 0.61 | 0.028* | |
C15 | 0.1960 (2) | 0.6065 (2) | 0.57080 (10) | 0.0239 (5) | |
H15 | 0.2217 | 0.6989 | 0.5706 | 0.029* | |
C16 | 0.2802 (2) | 0.5091 (2) | 0.54814 (9) | 0.0192 (4) | |
H16 | 0.3645 | 0.534 | 0.533 | 0.023* | |
C17 | 0.1881 (2) | 0.1073 (2) | 0.45782 (9) | 0.0184 (4) | |
H17 | 0.1429 | 0.1845 | 0.4379 | 0.022* | |
C18 | 0.1510 (2) | −0.0242 (2) | 0.42880 (9) | 0.0190 (4) | |
C19 | 0.0453 (2) | −0.02757 (19) | 0.36781 (9) | 0.0180 (4) | |
C20 | −0.0602 (2) | 0.0635 (2) | 0.36431 (10) | 0.0229 (4) | |
H20 | −0.0665 | 0.1277 | 0.4012 | 0.028* | |
C21 | −0.1566 (2) | 0.0614 (2) | 0.30726 (11) | 0.0274 (5) | |
H21 | −0.2288 | 0.1237 | 0.3052 | 0.033* | |
C22 | −0.1475 (2) | −0.0312 (2) | 0.25364 (11) | 0.0306 (5) | |
H22 | −0.2125 | −0.0317 | 0.2142 | 0.037* | |
C23 | −0.0439 (2) | −0.1231 (2) | 0.25727 (11) | 0.0299 (5) | |
H23 | −0.0386 | −0.1875 | 0.2205 | 0.036* | |
C24 | 0.0531 (2) | −0.1223 (2) | 0.31447 (10) | 0.0236 (4) | |
H24 | 0.124 | −0.1862 | 0.3169 | 0.028* | |
N | 0.35095 (17) | 0.02378 (17) | 0.54652 (8) | 0.0185 (4) | |
O1 | 0.77149 (15) | −0.07201 (15) | 0.80900 (7) | 0.0256 (4) | |
O2 | 0.71416 (15) | 0.14014 (14) | 0.83548 (7) | 0.0235 (3) | |
O3 | 0.44788 (14) | 0.29599 (14) | 0.51058 (7) | 0.0209 (3) | |
O4 | 0.20445 (15) | −0.13062 (14) | 0.45119 (7) | 0.0253 (3) | |
H1 | 0.327 (2) | −0.056 (2) | 0.5293 (11) | 0.022 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0344 (14) | 0.0390 (13) | 0.0206 (9) | 0.0117 (11) | −0.0092 (9) | 0.0008 (9) |
C2 | 0.0166 (10) | 0.0200 (10) | 0.0156 (8) | −0.0012 (8) | 0.0014 (7) | 0.0044 (7) |
C3 | 0.0186 (10) | 0.0176 (10) | 0.0149 (8) | −0.0002 (8) | 0.0025 (7) | 0.0025 (6) |
C4 | 0.0193 (10) | 0.0172 (9) | 0.0183 (8) | 0.0036 (8) | 0.0019 (7) | 0.0034 (7) |
C5 | 0.0226 (11) | 0.0166 (9) | 0.0165 (8) | −0.0006 (8) | 0.0031 (7) | −0.0011 (7) |
C6 | 0.0163 (10) | 0.0186 (9) | 0.0149 (8) | −0.0010 (8) | 0.0004 (7) | 0.0025 (7) |
C7 | 0.0240 (11) | 0.0189 (10) | 0.0177 (8) | 0.0062 (8) | 0.0014 (8) | 0.0007 (7) |
C8 | 0.0259 (11) | 0.0193 (10) | 0.0151 (8) | 0.0017 (8) | 0.0023 (7) | −0.0006 (7) |
C9 | 0.0178 (10) | 0.0194 (10) | 0.0155 (8) | 0.0004 (8) | 0.0028 (7) | −0.0008 (7) |
C10 | 0.0196 (10) | 0.0199 (10) | 0.0117 (7) | −0.0006 (8) | −0.0036 (7) | 0.0010 (7) |
C11 | 0.0200 (10) | 0.0191 (10) | 0.0127 (7) | 0.0010 (8) | −0.0017 (7) | 0.0002 (6) |
C12 | 0.0230 (11) | 0.0215 (10) | 0.0217 (9) | −0.0011 (8) | 0.0029 (8) | −0.0008 (7) |
C13 | 0.0210 (11) | 0.0275 (11) | 0.0260 (9) | 0.0023 (9) | 0.0062 (8) | 0.0005 (8) |
C14 | 0.0247 (12) | 0.0223 (10) | 0.0226 (9) | 0.0078 (9) | 0.0027 (8) | 0.0009 (8) |
C15 | 0.0310 (12) | 0.0177 (10) | 0.0227 (9) | 0.0027 (9) | −0.0005 (8) | 0.0019 (7) |
C16 | 0.0201 (11) | 0.0203 (10) | 0.0169 (8) | −0.0004 (8) | 0.0005 (7) | 0.0021 (7) |
C17 | 0.0196 (11) | 0.0160 (9) | 0.0189 (8) | 0.0001 (8) | −0.0017 (7) | 0.0001 (7) |
C18 | 0.0193 (10) | 0.0201 (10) | 0.0174 (8) | −0.0021 (8) | 0.0009 (7) | −0.0009 (7) |
C19 | 0.0194 (10) | 0.0180 (9) | 0.0166 (8) | −0.0070 (8) | 0.0015 (7) | 0.0015 (7) |
C20 | 0.0221 (11) | 0.0217 (10) | 0.0247 (9) | −0.0040 (9) | 0.0007 (8) | −0.0033 (8) |
C21 | 0.0177 (11) | 0.0303 (12) | 0.0332 (10) | −0.0011 (9) | −0.0026 (9) | −0.0003 (9) |
C22 | 0.0243 (12) | 0.0440 (14) | 0.0224 (9) | −0.0079 (10) | −0.0039 (9) | −0.0023 (9) |
C23 | 0.0310 (13) | 0.0358 (13) | 0.0227 (9) | −0.0061 (10) | 0.0014 (9) | −0.0108 (9) |
C24 | 0.0255 (12) | 0.0223 (11) | 0.0233 (9) | −0.0015 (9) | 0.0041 (8) | −0.0032 (8) |
N | 0.0235 (10) | 0.0158 (8) | 0.0157 (7) | 0.0000 (7) | −0.0020 (7) | −0.0019 (6) |
O1 | 0.0293 (9) | 0.0290 (8) | 0.0171 (6) | 0.0100 (7) | −0.0065 (6) | −0.0011 (5) |
O2 | 0.0290 (9) | 0.0210 (8) | 0.0199 (6) | −0.0029 (6) | −0.0025 (6) | −0.0006 (5) |
O3 | 0.0180 (8) | 0.0235 (8) | 0.0209 (6) | −0.0018 (6) | 0.0005 (5) | −0.0027 (5) |
O4 | 0.0313 (9) | 0.0179 (7) | 0.0256 (7) | 0.0016 (6) | −0.0041 (6) | 0.0014 (5) |
C1—O1 | 1.444 (2) | C12—C13 | 1.383 (3) |
C1—H1A | 0.98 | C12—H12 | 0.95 |
C1—H1B | 0.98 | C13—C14 | 1.378 (3) |
C1—H1C | 0.98 | C13—H13 | 0.95 |
C2—O2 | 1.207 (2) | C14—C15 | 1.392 (3) |
C2—O1 | 1.338 (2) | C14—H14 | 0.95 |
C2—C3 | 1.481 (2) | C15—C16 | 1.375 (3) |
C3—C8 | 1.390 (3) | C15—H15 | 0.95 |
C3—C4 | 1.393 (3) | C16—H16 | 0.95 |
C4—C5 | 1.384 (2) | C17—C18 | 1.448 (3) |
C4—H4 | 0.95 | C17—H17 | 0.95 |
C5—C6 | 1.392 (3) | C18—O4 | 1.240 (2) |
C5—H5 | 0.95 | C18—C19 | 1.501 (3) |
C6—C7 | 1.393 (3) | C19—C24 | 1.386 (3) |
C6—N | 1.404 (2) | C19—C20 | 1.388 (3) |
C7—C8 | 1.384 (3) | C20—C21 | 1.388 (3) |
C7—H7 | 0.95 | C20—H20 | 0.95 |
C8—H8 | 0.95 | C21—C22 | 1.377 (3) |
C9—N | 1.353 (2) | C21—H21 | 0.95 |
C9—C17 | 1.361 (3) | C22—C23 | 1.378 (3) |
C9—C10 | 1.517 (3) | C22—H22 | 0.95 |
C10—O3 | 1.220 (2) | C23—C24 | 1.394 (3) |
C10—C11 | 1.476 (3) | C23—H23 | 0.95 |
C11—C12 | 1.395 (3) | C24—H24 | 0.95 |
C11—C16 | 1.396 (3) | N—H1 | 0.88 (2) |
O1—C1—H1A | 109.5 | C14—C13—H13 | 119.9 |
O1—C1—H1B | 109.5 | C12—C13—H13 | 119.9 |
H1A—C1—H1B | 109.5 | C13—C14—C15 | 120.08 (19) |
O1—C1—H1C | 109.5 | C13—C14—H14 | 120 |
H1A—C1—H1C | 109.5 | C15—C14—H14 | 120 |
H1B—C1—H1C | 109.5 | C16—C15—C14 | 120.3 (2) |
O2—C2—O1 | 123.59 (17) | C16—C15—H15 | 119.9 |
O2—C2—C3 | 124.49 (18) | C14—C15—H15 | 119.9 |
O1—C2—C3 | 111.90 (16) | C15—C16—C11 | 119.8 (2) |
C8—C3—C4 | 119.20 (17) | C15—C16—H16 | 120.1 |
C8—C3—C2 | 118.48 (17) | C11—C16—H16 | 120.1 |
C4—C3—C2 | 122.32 (17) | C9—C17—C18 | 123.66 (18) |
C5—C4—C3 | 120.29 (18) | C9—C17—H17 | 118.2 |
C5—C4—H4 | 119.9 | C18—C17—H17 | 118.2 |
C3—C4—H4 | 119.9 | O4—C18—C17 | 122.89 (17) |
C4—C5—C6 | 120.24 (17) | O4—C18—C19 | 120.07 (17) |
C4—C5—H5 | 119.9 | C17—C18—C19 | 117.03 (17) |
C6—C5—H5 | 119.9 | C24—C19—C20 | 119.69 (18) |
C5—C6—C7 | 119.59 (17) | C24—C19—C18 | 119.77 (18) |
C5—C6—N | 117.80 (17) | C20—C19—C18 | 120.54 (17) |
C7—C6—N | 122.58 (17) | C21—C20—C19 | 120.32 (19) |
C8—C7—C6 | 119.82 (18) | C21—C20—H20 | 119.8 |
C8—C7—H7 | 120.1 | C19—C20—H20 | 119.8 |
C6—C7—H7 | 120.1 | C22—C21—C20 | 120.0 (2) |
C7—C8—C3 | 120.77 (18) | C22—C21—H21 | 120 |
C7—C8—H8 | 119.6 | C20—C21—H21 | 120 |
C3—C8—H8 | 119.6 | C21—C22—C23 | 119.96 (19) |
N—C9—C17 | 123.33 (18) | C21—C22—H22 | 120 |
N—C9—C10 | 119.14 (16) | C23—C22—H22 | 120 |
C17—C9—C10 | 116.57 (16) | C22—C23—C24 | 120.58 (19) |
O3—C10—C11 | 122.91 (18) | C22—C23—H23 | 119.7 |
O3—C10—C9 | 117.87 (17) | C24—C23—H23 | 119.7 |
C11—C10—C9 | 119.12 (17) | C19—C24—C23 | 119.5 (2) |
C12—C11—C16 | 119.70 (18) | C19—C24—H24 | 120.3 |
C12—C11—C10 | 121.16 (18) | C23—C24—H24 | 120.3 |
C16—C11—C10 | 119.12 (18) | C9—N—C6 | 127.71 (17) |
C13—C12—C11 | 119.97 (19) | C9—N—H1 | 112.7 (14) |
C13—C12—H12 | 120 | C6—N—H1 | 119.1 (14) |
C11—C12—H12 | 120 | C2—O1—C1 | 116.72 (16) |
C14—C13—C12 | 120.1 (2) | ||
O2—C2—C3—C8 | −7.7 (3) | C13—C14—C15—C16 | −0.5 (3) |
O1—C2—C3—C8 | 170.72 (18) | C14—C15—C16—C11 | 0.9 (3) |
O2—C2—C3—C4 | 173.1 (2) | C12—C11—C16—C15 | −0.8 (3) |
O1—C2—C3—C4 | −8.5 (3) | C10—C11—C16—C15 | −179.03 (16) |
C8—C3—C4—C5 | 1.5 (3) | N—C9—C17—C18 | −3.0 (3) |
C2—C3—C4—C5 | −179.27 (18) | C10—C9—C17—C18 | 165.61 (18) |
C3—C4—C5—C6 | 0.1 (3) | C9—C17—C18—O4 | −0.1 (3) |
C4—C5—C6—C7 | −2.6 (3) | C9—C17—C18—C19 | −178.55 (18) |
C4—C5—C6—N | 179.32 (18) | O4—C18—C19—C24 | −33.9 (3) |
C5—C6—C7—C8 | 3.7 (3) | C17—C18—C19—C24 | 144.54 (19) |
N—C6—C7—C8 | −178.39 (18) | O4—C18—C19—C20 | 146.1 (2) |
C6—C7—C8—C3 | −2.1 (3) | C17—C18—C19—C20 | −35.4 (3) |
C4—C3—C8—C7 | −0.4 (3) | C24—C19—C20—C21 | −0.9 (3) |
C2—C3—C8—C7 | −179.72 (18) | C18—C19—C20—C21 | 178.98 (19) |
N—C9—C10—O3 | 58.6 (2) | C19—C20—C21—C22 | −0.2 (3) |
C17—C9—C10—O3 | −110.5 (2) | C20—C21—C22—C23 | 1.1 (3) |
N—C9—C10—C11 | −124.84 (18) | C21—C22—C23—C24 | −0.8 (4) |
C17—C9—C10—C11 | 66.0 (2) | C20—C19—C24—C23 | 1.2 (3) |
O3—C10—C11—C12 | −172.08 (17) | C18—C19—C24—C23 | −178.67 (19) |
C9—C10—C11—C12 | 11.6 (2) | C22—C23—C24—C19 | −0.4 (3) |
O3—C10—C11—C16 | 6.1 (3) | C17—C9—N—C6 | −169.39 (19) |
C9—C10—C11—C16 | −170.22 (16) | C10—C9—N—C6 | 22.2 (3) |
C16—C11—C12—C13 | 0.2 (3) | C5—C6—N—C9 | −160.62 (19) |
C10—C11—C12—C13 | 178.45 (17) | C7—C6—N—C9 | 21.4 (3) |
C11—C12—C13—C14 | 0.2 (3) | O2—C2—O1—C1 | −0.3 (3) |
C12—C13—C14—C15 | −0.1 (3) | C3—C2—O1—C1 | −178.74 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1···O4 | 0.88 (2) | 1.99 (2) | 2.703 (2) | 138 (2) |
C1—H1B···O3i | 0.98 | 2.55 | 3.068 (2) | 113 |
C1—H1C···O2 | 0.98 | 2.31 | 2.671 (3) | 101 |
C4—H4···O2i | 0.95 | 2.49 | 3.368 (2) | 154 |
C5—H5···O3ii | 0.95 | 2.46 | 3.386 (2) | 165 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1. |