Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604027X/ci2180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680604027X/ci2180Isup2.hkl |
CCDC reference: 627453
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
C23H20N2O3 | F(000) = 1568 |
Mr = 372.41 | Dx = 1.305 Mg m−3 Dm = 1.303 (5) Mg m−3 Dm measured by flotation in aqueous potassium iodide |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.752 (5) Å | θ = 2–25° |
b = 21.259 (5) Å | µ = 0.09 mm−1 |
c = 23.011 (5) Å | T = 293 K |
V = 3792 (3) Å3 | Needle, light yellow |
Z = 8 | 0.5 × 0.2 × 0.2 mm |
Bruker SMART CCD area-detector diffractometer | 3248 independent reflections |
Radiation source: fine-focus sealed tube | 2428 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω–φ scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.963, Tmax = 0.983 | k = −25→25 |
17200 measured reflections | l = −13→27 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.8341P] where P = (Fo2 + 2Fc2)/3 |
3248 reflections | (Δ/σ)max = 0.003 |
254 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 | ||
N1 | 0.4339 (4) | 0.34106 (11) | 0.26852 (11) | 0.0371 (7) | |
N2 | 0.6415 (4) | 0.16179 (12) | 0.15768 (12) | 0.0406 (7) | |
H2A | 0.6583 | 0.1551 | 0.1212 | 0.049* | |
H2B | 0.6668 | 0.1331 | 0.1826 | 0.049* | |
O1 | 0.4696 (3) | 0.31784 (9) | 0.17121 (9) | 0.0406 (6) | |
O2 | 0.5965 (3) | 0.22681 (11) | 0.04856 (10) | 0.0549 (7) | |
O3 | 0.4814 (3) | 0.32372 (11) | 0.05580 (9) | 0.0453 (6) | |
C1 | 0.4778 (4) | 0.30035 (14) | 0.22761 (14) | 0.0339 (8) | |
C2 | 0.5366 (4) | 0.23864 (13) | 0.23381 (14) | 0.0319 (7) | |
C3 | 0.5464 (4) | 0.21530 (13) | 0.29078 (13) | 0.0297 (7) | |
C4 | 0.5051 (4) | 0.25748 (14) | 0.33449 (14) | 0.0342 (8) | |
H4 | 0.5138 | 0.2444 | 0.3730 | 0.041* | |
C5 | 0.4504 (4) | 0.31923 (14) | 0.32290 (13) | 0.0321 (7) | |
C6 | 0.5926 (4) | 0.14910 (13) | 0.30497 (13) | 0.0294 (7) | |
C7 | 0.5202 (4) | 0.09894 (14) | 0.27464 (14) | 0.0369 (8) | |
H7 | 0.4442 | 0.1069 | 0.2443 | 0.044* | |
C8 | 0.5596 (4) | 0.03753 (15) | 0.28898 (15) | 0.0415 (9) | |
H8 | 0.5090 | 0.0049 | 0.2682 | 0.050* | |
C9 | 0.6727 (4) | 0.02357 (14) | 0.33360 (14) | 0.0374 (8) | |
C10 | 0.7442 (4) | 0.07355 (15) | 0.36379 (14) | 0.0386 (8) | |
H10 | 0.8205 | 0.0654 | 0.3941 | 0.046* | |
C11 | 0.7051 (4) | 0.13478 (14) | 0.35007 (13) | 0.0334 (8) | |
H11 | 0.7549 | 0.1672 | 0.3713 | 0.040* | |
C12 | 0.7166 (6) | −0.04341 (16) | 0.34857 (19) | 0.0651 (12) | |
H12A | 0.6131 | −0.0657 | 0.3586 | 0.098* | |
H12B | 0.7946 | −0.0440 | 0.3810 | 0.098* | |
H12C | 0.7702 | −0.0632 | 0.3157 | 0.098* | |
C13 | 0.4054 (4) | 0.36413 (14) | 0.37004 (14) | 0.0339 (8) | |
C14 | 0.4606 (5) | 0.35608 (15) | 0.42708 (14) | 0.0421 (9) | |
H14 | 0.5245 | 0.3206 | 0.4367 | 0.051* | |
C15 | 0.4227 (5) | 0.39950 (17) | 0.46955 (16) | 0.0499 (10) | |
H15 | 0.4599 | 0.3929 | 0.5075 | 0.060* | |
C16 | 0.3305 (5) | 0.45214 (18) | 0.45607 (17) | 0.0558 (11) | |
H16 | 0.3059 | 0.4817 | 0.4847 | 0.067* | |
C17 | 0.2737 (5) | 0.46146 (18) | 0.39988 (18) | 0.0589 (11) | |
H17 | 0.2111 | 0.4974 | 0.3906 | 0.071* | |
C18 | 0.3099 (5) | 0.41736 (15) | 0.35734 (16) | 0.0459 (9) | |
H18 | 0.2694 | 0.4236 | 0.3197 | 0.055* | |
C19 | 0.5747 (4) | 0.21780 (14) | 0.17585 (13) | 0.0306 (7) | |
C20 | 0.5298 (4) | 0.26665 (14) | 0.14008 (14) | 0.0361 (8) | |
C21 | 0.5402 (4) | 0.26973 (15) | 0.07779 (15) | 0.0397 (8) | |
C22 | 0.4896 (5) | 0.33011 (17) | −0.00671 (15) | 0.0495 (10) | |
H22A | 0.4254 | 0.2965 | −0.0253 | 0.059* | |
H22B | 0.6084 | 0.3281 | −0.0198 | 0.059* | |
C23 | 0.4127 (5) | 0.39236 (18) | −0.02169 (17) | 0.0597 (11) | |
H23A | 0.4169 | 0.3984 | −0.0630 | 0.089* | |
H23B | 0.4768 | 0.4252 | −0.0028 | 0.089* | |
H23C | 0.2949 | 0.3936 | −0.0089 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0493 (18) | 0.0251 (14) | 0.0370 (16) | 0.0039 (12) | 0.0042 (13) | 0.0006 (12) |
N2 | 0.0522 (18) | 0.0315 (15) | 0.0381 (16) | 0.0079 (13) | 0.0051 (13) | −0.0031 (12) |
O1 | 0.0607 (16) | 0.0285 (12) | 0.0327 (13) | 0.0072 (11) | 0.0030 (11) | 0.0024 (10) |
O2 | 0.0746 (19) | 0.0472 (15) | 0.0429 (15) | 0.0145 (14) | 0.0006 (13) | −0.0091 (12) |
O3 | 0.0631 (17) | 0.0405 (13) | 0.0323 (13) | 0.0069 (12) | 0.0000 (11) | 0.0026 (11) |
C1 | 0.041 (2) | 0.0256 (16) | 0.0350 (19) | 0.0017 (14) | 0.0015 (15) | 0.0034 (15) |
C2 | 0.0351 (18) | 0.0264 (16) | 0.0341 (19) | −0.0009 (14) | 0.0008 (15) | 0.0015 (14) |
C3 | 0.0297 (18) | 0.0247 (16) | 0.0348 (18) | −0.0020 (13) | 0.0004 (14) | −0.0013 (13) |
C4 | 0.040 (2) | 0.0326 (17) | 0.0298 (17) | −0.0012 (15) | 0.0017 (15) | 0.0045 (15) |
C5 | 0.0348 (19) | 0.0269 (16) | 0.0345 (19) | −0.0023 (14) | 0.0055 (14) | −0.0012 (14) |
C6 | 0.0345 (18) | 0.0229 (16) | 0.0308 (17) | 0.0011 (14) | 0.0054 (14) | 0.0042 (13) |
C7 | 0.0375 (19) | 0.0330 (18) | 0.0402 (19) | −0.0005 (15) | −0.0057 (15) | 0.0031 (15) |
C8 | 0.045 (2) | 0.0289 (17) | 0.050 (2) | −0.0037 (16) | −0.0042 (17) | −0.0012 (16) |
C9 | 0.039 (2) | 0.0279 (18) | 0.045 (2) | 0.0018 (15) | 0.0010 (16) | 0.0054 (15) |
C10 | 0.038 (2) | 0.042 (2) | 0.0354 (19) | 0.0035 (16) | −0.0023 (15) | 0.0078 (16) |
C11 | 0.0392 (19) | 0.0277 (17) | 0.0333 (18) | −0.0018 (15) | 0.0032 (14) | 0.0010 (14) |
C12 | 0.076 (3) | 0.037 (2) | 0.082 (3) | 0.007 (2) | −0.007 (2) | 0.011 (2) |
C13 | 0.0362 (19) | 0.0288 (17) | 0.0368 (19) | −0.0027 (15) | 0.0035 (14) | −0.0010 (14) |
C14 | 0.054 (2) | 0.0306 (18) | 0.042 (2) | 0.0033 (16) | 0.0029 (17) | −0.0003 (16) |
C15 | 0.062 (3) | 0.047 (2) | 0.041 (2) | 0.0003 (19) | 0.0016 (18) | −0.0089 (18) |
C16 | 0.064 (3) | 0.048 (2) | 0.056 (3) | 0.011 (2) | 0.005 (2) | −0.0240 (19) |
C17 | 0.067 (3) | 0.048 (2) | 0.062 (3) | 0.015 (2) | −0.001 (2) | −0.014 (2) |
C18 | 0.058 (3) | 0.0352 (19) | 0.044 (2) | 0.0088 (18) | −0.0028 (18) | −0.0072 (16) |
C19 | 0.0295 (18) | 0.0261 (17) | 0.0360 (19) | −0.0020 (13) | −0.0004 (14) | −0.0009 (14) |
C20 | 0.044 (2) | 0.0306 (18) | 0.0342 (19) | 0.0024 (15) | 0.0052 (15) | −0.0069 (15) |
C21 | 0.046 (2) | 0.0339 (19) | 0.039 (2) | 0.0006 (16) | 0.0007 (17) | −0.0043 (17) |
C22 | 0.057 (3) | 0.058 (2) | 0.033 (2) | 0.0004 (19) | 0.0004 (17) | 0.0049 (17) |
C23 | 0.062 (3) | 0.065 (3) | 0.052 (2) | 0.010 (2) | −0.002 (2) | 0.017 (2) |
N1—C1 | 1.323 (4) | C10—C11 | 1.373 (4) |
N1—C5 | 1.341 (4) | C10—H10 | 0.93 |
N2—C19 | 1.364 (4) | C11—H11 | 0.93 |
N2—H2A | 0.86 | C12—H12A | 0.96 |
N2—H2B | 0.86 | C12—H12B | 0.96 |
O1—C1 | 1.352 (4) | C12—H12C | 0.96 |
O1—C20 | 1.384 (4) | C13—C18 | 1.384 (4) |
O2—C21 | 1.214 (4) | C13—C14 | 1.391 (4) |
O3—C21 | 1.335 (4) | C14—C15 | 1.376 (5) |
O3—C22 | 1.446 (4) | C14—H14 | 0.93 |
C1—C2 | 1.396 (4) | C15—C16 | 1.364 (5) |
C2—C3 | 1.404 (4) | C15—H15 | 0.93 |
C2—C19 | 1.436 (4) | C16—C17 | 1.380 (5) |
C3—C4 | 1.385 (4) | C16—H16 | 0.93 |
C3—C6 | 1.488 (4) | C17—C18 | 1.384 (5) |
C4—C5 | 1.405 (4) | C17—H17 | 0.93 |
C4—H4 | 0.93 | C18—H18 | 0.93 |
C5—C13 | 1.486 (4) | C19—C20 | 1.370 (4) |
C6—C11 | 1.390 (4) | C20—C21 | 1.437 (5) |
C6—C7 | 1.393 (4) | C22—C23 | 1.492 (5) |
C7—C8 | 1.381 (4) | C22—H22A | 0.97 |
C7—H7 | 0.93 | C22—H22B | 0.97 |
C8—C9 | 1.383 (5) | C23—H23A | 0.96 |
C8—H8 | 0.93 | C23—H23B | 0.96 |
C9—C10 | 1.385 (4) | C23—H23C | 0.96 |
C9—C12 | 1.504 (4) | ||
C1—N1—C5 | 114.4 (3) | C9—C12—H12C | 109.5 |
C19—N2—H2A | 120.0 | H12A—C12—H12C | 109.5 |
C19—N2—H2B | 120.0 | H12B—C12—H12C | 109.5 |
H2A—N2—H2B | 120.0 | C18—C13—C14 | 117.7 (3) |
C1—O1—C20 | 105.4 (2) | C18—C13—C5 | 119.8 (3) |
C21—O3—C22 | 116.3 (3) | C14—C13—C5 | 122.5 (3) |
N1—C1—O1 | 119.4 (3) | C15—C14—C13 | 121.5 (3) |
N1—C1—C2 | 128.7 (3) | C15—C14—H14 | 119.3 |
O1—C1—C2 | 111.8 (3) | C13—C14—H14 | 119.3 |
C1—C2—C3 | 116.4 (3) | C16—C15—C14 | 120.1 (4) |
C1—C2—C19 | 105.2 (3) | C16—C15—H15 | 120.0 |
C3—C2—C19 | 138.3 (3) | C14—C15—H15 | 120.0 |
C4—C3—C2 | 115.9 (3) | C15—C16—C17 | 119.9 (3) |
C4—C3—C6 | 120.6 (3) | C15—C16—H16 | 120.1 |
C2—C3—C6 | 123.5 (3) | C17—C16—H16 | 120.1 |
C3—C4—C5 | 122.5 (3) | C16—C17—C18 | 120.1 (4) |
C3—C4—H4 | 118.8 | C16—C17—H17 | 120.0 |
C5—C4—H4 | 118.8 | C18—C17—H17 | 120.0 |
N1—C5—C4 | 122.0 (3) | C13—C18—C17 | 120.9 (3) |
N1—C5—C13 | 115.9 (3) | C13—C18—H18 | 119.6 |
C4—C5—C13 | 122.2 (3) | C17—C18—H18 | 119.6 |
C11—C6—C7 | 117.3 (3) | N2—C19—C20 | 125.0 (3) |
C11—C6—C3 | 121.5 (3) | N2—C19—C2 | 129.2 (3) |
C7—C6—C3 | 121.2 (3) | C20—C19—C2 | 105.8 (3) |
C8—C7—C6 | 121.0 (3) | C19—C20—O1 | 111.8 (3) |
C8—C7—H7 | 119.5 | C19—C20—C21 | 128.3 (3) |
C6—C7—H7 | 119.5 | O1—C20—C21 | 119.9 (3) |
C7—C8—C9 | 121.4 (3) | O2—C21—O3 | 124.0 (3) |
C7—C8—H8 | 119.3 | O2—C21—C20 | 122.6 (3) |
C9—C8—H8 | 119.3 | O3—C21—C20 | 113.5 (3) |
C8—C9—C10 | 117.5 (3) | O3—C22—C23 | 107.2 (3) |
C8—C9—C12 | 121.1 (3) | O3—C22—H22A | 110.3 |
C10—C9—C12 | 121.4 (3) | C23—C22—H22A | 110.3 |
C11—C10—C9 | 121.6 (3) | O3—C22—H22B | 110.3 |
C11—C10—H10 | 119.2 | C23—C22—H22B | 110.3 |
C9—C10—H10 | 119.2 | H22A—C22—H22B | 108.5 |
C10—C11—C6 | 121.2 (3) | C22—C23—H23A | 109.5 |
C10—C11—H11 | 119.4 | C22—C23—H23B | 109.5 |
C6—C11—H11 | 119.4 | H23A—C23—H23B | 109.5 |
C9—C12—H12A | 109.5 | C22—C23—H23C | 109.5 |
C9—C12—H12B | 109.5 | H23A—C23—H23C | 109.5 |
H12A—C12—H12B | 109.5 | H23B—C23—H23C | 109.5 |
C5—N1—C1—O1 | −178.6 (3) | C3—C6—C11—C10 | 178.5 (3) |
C5—N1—C1—C2 | 0.5 (5) | N1—C5—C13—C18 | 16.7 (4) |
C20—O1—C1—N1 | 177.5 (3) | C4—C5—C13—C18 | −162.7 (3) |
C20—O1—C1—C2 | −1.8 (4) | N1—C5—C13—C14 | −161.1 (3) |
N1—C1—C2—C3 | 2.1 (5) | C4—C5—C13—C14 | 19.5 (5) |
O1—C1—C2—C3 | −178.7 (3) | C18—C13—C14—C15 | −0.3 (5) |
N1—C1—C2—C19 | −176.5 (3) | C5—C13—C14—C15 | 177.6 (3) |
O1—C1—C2—C19 | 2.7 (4) | C13—C14—C15—C16 | −0.6 (6) |
C1—C2—C3—C4 | −3.3 (4) | C14—C15—C16—C17 | 0.7 (6) |
C19—C2—C3—C4 | 174.7 (4) | C15—C16—C17—C18 | 0.2 (6) |
C1—C2—C3—C6 | 174.9 (3) | C14—C13—C18—C17 | 1.2 (5) |
C19—C2—C3—C6 | −7.2 (6) | C5—C13—C18—C17 | −176.7 (3) |
C2—C3—C4—C5 | 2.3 (5) | C16—C17—C18—C13 | −1.1 (6) |
C6—C3—C4—C5 | −175.9 (3) | C1—C2—C19—N2 | 177.6 (3) |
C1—N1—C5—C4 | −1.8 (4) | C3—C2—C19—N2 | −0.5 (6) |
C1—N1—C5—C13 | 178.9 (3) | C1—C2—C19—C20 | −2.5 (3) |
C3—C4—C5—N1 | 0.4 (5) | C3—C2—C19—C20 | 179.5 (4) |
C3—C4—C5—C13 | 179.7 (3) | N2—C19—C20—O1 | −178.5 (3) |
C4—C3—C6—C11 | −44.9 (4) | C2—C19—C20—O1 | 1.5 (4) |
C2—C3—C6—C11 | 137.1 (3) | N2—C19—C20—C21 | 0.8 (5) |
C4—C3—C6—C7 | 133.1 (3) | C2—C19—C20—C21 | −179.1 (3) |
C2—C3—C6—C7 | −44.9 (4) | C1—O1—C20—C19 | 0.1 (4) |
C11—C6—C7—C8 | −0.1 (5) | C1—O1—C20—C21 | −179.3 (3) |
C3—C6—C7—C8 | −178.2 (3) | C22—O3—C21—O2 | −0.9 (5) |
C6—C7—C8—C9 | −0.4 (5) | C22—O3—C21—C20 | 179.5 (3) |
C7—C8—C9—C10 | 0.5 (5) | C19—C20—C21—O2 | −1.4 (6) |
C7—C8—C9—C12 | −179.3 (3) | O1—C20—C21—O2 | 178.0 (3) |
C8—C9—C10—C11 | −0.2 (5) | C19—C20—C21—O3 | 178.2 (3) |
C12—C9—C10—C11 | 179.7 (3) | O1—C20—C21—O3 | −2.4 (4) |
C9—C10—C11—C6 | −0.3 (5) | C21—O3—C22—C23 | 178.1 (3) |
C7—C6—C11—C10 | 0.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.31 | 2.887 (4) | 124 |
C7—H7···Cg1i | 0.93 | 2.86 | 3.713 (4) | 153 |
C12—H12B···Cg2ii | 0.96 | 2.91 | 3.699 (5) | 140 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+3/2, y−1/2, z. |