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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.078
- wR factor = 0.166
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
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 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: 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. |
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