Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010517/wn6243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010517/wn6243Isup2.hkl |
CCDC reference: 242305
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.058
- wR factor = 0.133
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H3 .. H14 .. 2.09 Ang.
Alert level C DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.672 Test value = -0.600 DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.107 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.67 e/A 3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. CG3 .. 2.83 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. CG4 .. 3.06 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H19N3O2 | F(000) = 800 |
Mr = 381.42 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6124 reflections |
a = 8.6587 (10) Å | θ = 2.0–26.3° |
b = 20.5881 (19) Å | µ = 0.09 mm−1 |
c = 11.0082 (13) Å | T = 293 K |
β = 100.187 (9)° | Prism, colourless |
V = 1931.5 (4) Å3 | 0.29 × 0.17 × 0.09 mm |
Z = 4 |
Stoe IPDS-2 diffractometer | 3400 independent reflections |
Radiation source: sealed X-ray tube | 1440 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.107 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
w rotation scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −24→24 |
Tmin = 0.983, Tmax = 0.992 | l = −13→13 |
20198 measured reflections |
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)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0427P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3400 reflections | Δρmax = 0.49 e Å−3 |
251 parameters | Δρmin = −0.67 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0091 (11) |
Experimental. Solvents were dried by refluxing with the appropriate drying agents and distilled before use. All other reagents were purchased from Merck, Fluka, Aldrich and Acros Chemical Co., and used without further purification. Experiments were followed by TLC using DC Alufolien Kieselgel 60 F254 Merck and a Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with a rotary evaporator (Buchi RE model 111). The melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108. |
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. |
Refinement. 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 | 0.3468 (3) | 0.20355 (13) | 0.6187 (3) | 0.0674 (9) | |
O2 | 0.1797 (3) | 0.06184 (13) | 0.7844 (3) | 0.0650 (8) | |
N1 | 0.0017 (3) | 0.26731 (14) | 0.6910 (3) | 0.0489 (8) | |
N2 | −0.0980 (3) | 0.23662 (14) | 0.7561 (3) | 0.0469 (8) | |
N3 | 0.2076 (3) | 0.28783 (15) | 0.5345 (3) | 0.0542 (6) | |
H3 | 0.1203 | 0.3087 | 0.5246 | 0.065* | |
C1 | −0.0670 (4) | 0.17140 (17) | 0.7696 (3) | 0.0434 (9) | |
C2 | 0.0577 (4) | 0.15942 (17) | 0.7102 (3) | 0.0452 (10) | |
C3 | 0.0941 (4) | 0.21977 (18) | 0.6635 (3) | 0.0456 (10) | |
C4 | 0.2293 (4) | 0.2360 (2) | 0.6035 (4) | 0.0542 (6) | |
C5 | 0.3339 (4) | 0.30893 (19) | 0.4755 (4) | 0.0542 (6) | |
H5A | 0.3032 | 0.3476 | 0.4287 | 0.081* | |
H5B | 0.3584 | 0.2754 | 0.4213 | 0.081* | |
H5C | 0.4246 | 0.3179 | 0.5370 | 0.081* | |
C6 | 0.1321 (4) | 0.09558 (19) | 0.6940 (4) | 0.0508 (10) | |
C7 | 0.1501 (4) | 0.07440 (18) | 0.5681 (4) | 0.0502 (10) | |
C8 | 0.0698 (5) | 0.1029 (2) | 0.4638 (4) | 0.0635 (12) | |
H8 | 0.0004 | 0.1366 | 0.4706 | 0.076* | |
C9 | 0.0905 (5) | 0.0822 (2) | 0.3471 (4) | 0.0716 (13) | |
H9 | 0.0367 | 0.1025 | 0.2767 | 0.086* | |
C10 | 0.1893 (5) | 0.0324 (2) | 0.3370 (5) | 0.0714 (13) | |
H10 | 0.2031 | 0.0181 | 0.2595 | 0.086* | |
C11 | 0.2691 (5) | 0.0031 (2) | 0.4413 (5) | 0.0781 (14) | |
H11 | 0.3374 | −0.0309 | 0.4337 | 0.094* | |
C12 | 0.2500 (5) | 0.0232 (2) | 0.5567 (4) | 0.0664 (13) | |
H12 | 0.3037 | 0.0024 | 0.6267 | 0.080* | |
C13 | −0.1578 (4) | 0.12776 (17) | 0.8364 (3) | 0.0439 (10) | |
C14 | −0.0810 (4) | 0.09463 (18) | 0.9396 (4) | 0.0543 (11) | |
H14 | 0.0262 | 0.1006 | 0.9657 | 0.065* | |
C15 | −0.1623 (5) | 0.05295 (19) | 1.0038 (4) | 0.0612 (11) | |
H15 | −0.1098 | 0.0311 | 1.0729 | 0.073* | |
C16 | −0.3193 (5) | 0.0439 (2) | 0.9659 (4) | 0.0667 (13) | |
H16 | −0.3735 | 0.0156 | 1.0092 | 0.080* | |
C17 | −0.3988 (5) | 0.0763 (2) | 0.8637 (4) | 0.0645 (12) | |
H17 | −0.5060 | 0.0700 | 0.8385 | 0.077* | |
C18 | −0.3182 (4) | 0.11816 (18) | 0.7995 (4) | 0.0529 (11) | |
H18 | −0.3717 | 0.1401 | 0.7309 | 0.063* | |
C19 | −0.2127 (4) | 0.27546 (18) | 0.8027 (4) | 0.0456 (9) | |
C20 | −0.2435 (4) | 0.26439 (19) | 0.9188 (4) | 0.0551 (11) | |
H20 | −0.1899 | 0.2321 | 0.9684 | 0.066* | |
C21 | −0.3560 (5) | 0.3021 (2) | 0.9614 (4) | 0.0630 (12) | |
H21 | −0.3789 | 0.2947 | 1.0397 | 0.076* | |
C22 | −0.4336 (5) | 0.3502 (2) | 0.8885 (5) | 0.0738 (14) | |
H22 | −0.5100 | 0.3748 | 0.9168 | 0.089* | |
C23 | −0.3980 (5) | 0.3620 (2) | 0.7735 (5) | 0.0757 (14) | |
H23 | −0.4484 | 0.3954 | 0.7253 | 0.091* | |
C24 | −0.2877 (5) | 0.3243 (2) | 0.7288 (4) | 0.0612 (11) | |
H24 | −0.2646 | 0.3318 | 0.6507 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0522 (16) | 0.070 (2) | 0.086 (2) | 0.0114 (14) | 0.0271 (15) | 0.0208 (16) |
O2 | 0.0739 (19) | 0.063 (2) | 0.060 (2) | 0.0165 (15) | 0.0151 (16) | 0.0100 (16) |
N1 | 0.0545 (18) | 0.045 (2) | 0.051 (2) | −0.0045 (16) | 0.0203 (17) | 0.0016 (16) |
N2 | 0.0472 (18) | 0.045 (2) | 0.052 (2) | 0.0000 (16) | 0.0183 (16) | 0.0001 (16) |
N3 | 0.0412 (11) | 0.0658 (16) | 0.0593 (15) | 0.0054 (10) | 0.0193 (10) | 0.0219 (11) |
C1 | 0.044 (2) | 0.040 (2) | 0.048 (3) | −0.0020 (17) | 0.0133 (19) | −0.0010 (19) |
C2 | 0.047 (2) | 0.043 (2) | 0.047 (3) | 0.0006 (18) | 0.0119 (19) | 0.0015 (18) |
C3 | 0.044 (2) | 0.045 (2) | 0.049 (3) | 0.0030 (18) | 0.0137 (19) | 0.0007 (19) |
C4 | 0.0412 (11) | 0.0658 (16) | 0.0593 (15) | 0.0054 (10) | 0.0193 (10) | 0.0219 (11) |
C5 | 0.0412 (11) | 0.0658 (16) | 0.0593 (15) | 0.0054 (10) | 0.0193 (10) | 0.0219 (11) |
C6 | 0.046 (2) | 0.048 (3) | 0.060 (3) | 0.0019 (18) | 0.014 (2) | 0.003 (2) |
C7 | 0.053 (2) | 0.048 (3) | 0.052 (3) | 0.0031 (19) | 0.017 (2) | 0.001 (2) |
C8 | 0.074 (3) | 0.057 (3) | 0.058 (3) | 0.019 (2) | 0.006 (2) | −0.002 (2) |
C9 | 0.089 (3) | 0.065 (3) | 0.056 (3) | 0.018 (3) | 0.002 (3) | −0.002 (2) |
C10 | 0.085 (3) | 0.067 (3) | 0.064 (3) | 0.009 (3) | 0.019 (3) | −0.011 (3) |
C11 | 0.094 (4) | 0.069 (3) | 0.074 (4) | 0.030 (3) | 0.020 (3) | −0.008 (3) |
C12 | 0.077 (3) | 0.060 (3) | 0.063 (3) | 0.023 (2) | 0.015 (3) | 0.002 (2) |
C13 | 0.043 (2) | 0.041 (2) | 0.049 (3) | 0.0000 (17) | 0.0109 (19) | −0.0016 (19) |
C14 | 0.050 (2) | 0.057 (3) | 0.058 (3) | −0.001 (2) | 0.015 (2) | 0.001 (2) |
C15 | 0.068 (3) | 0.059 (3) | 0.059 (3) | −0.001 (2) | 0.018 (2) | 0.010 (2) |
C16 | 0.065 (3) | 0.064 (3) | 0.078 (4) | −0.012 (2) | 0.031 (3) | 0.007 (3) |
C17 | 0.047 (2) | 0.066 (3) | 0.083 (4) | −0.013 (2) | 0.019 (3) | 0.000 (3) |
C18 | 0.048 (2) | 0.055 (3) | 0.056 (3) | 0.0020 (19) | 0.011 (2) | −0.004 (2) |
C19 | 0.045 (2) | 0.045 (2) | 0.048 (3) | 0.0004 (18) | 0.010 (2) | −0.006 (2) |
C20 | 0.054 (2) | 0.061 (3) | 0.054 (3) | −0.001 (2) | 0.019 (2) | −0.006 (2) |
C21 | 0.067 (3) | 0.065 (3) | 0.062 (3) | −0.003 (2) | 0.025 (2) | −0.013 (2) |
C22 | 0.065 (3) | 0.074 (4) | 0.087 (4) | 0.006 (2) | 0.026 (3) | −0.023 (3) |
C23 | 0.079 (3) | 0.063 (3) | 0.087 (4) | 0.023 (3) | 0.021 (3) | −0.002 (3) |
C24 | 0.064 (3) | 0.060 (3) | 0.060 (3) | 0.008 (2) | 0.014 (2) | 0.001 (2) |
O1—C4 | 1.204 (4) | C11—C12 | 1.374 (5) |
O2—C6 | 1.224 (4) | C11—H11 | 0.9300 |
N1—C3 | 1.332 (4) | C12—H12 | 0.9300 |
N1—N2 | 1.370 (4) | C13—C14 | 1.390 (5) |
N2—C1 | 1.372 (4) | C13—C18 | 1.391 (5) |
N2—C19 | 1.439 (4) | C14—C15 | 1.381 (5) |
N3—C4 | 1.304 (4) | C14—H14 | 0.9300 |
N3—C5 | 1.434 (4) | C15—C16 | 1.363 (5) |
N3—H3 | 0.8600 | C15—H15 | 0.9300 |
C1—C2 | 1.380 (4) | C16—C17 | 1.383 (6) |
C1—C13 | 1.473 (5) | C16—H16 | 0.9300 |
C2—C3 | 1.402 (5) | C17—C18 | 1.379 (5) |
C2—C6 | 1.488 (5) | C17—H17 | 0.9300 |
C3—C4 | 1.480 (5) | C18—H18 | 0.9300 |
C5—H5A | 0.9600 | C19—C20 | 1.370 (5) |
C5—H5B | 0.9600 | C19—C24 | 1.381 (5) |
C5—H5C | 0.9600 | C20—C21 | 1.391 (5) |
C6—C7 | 1.487 (5) | C20—H20 | 0.9300 |
C7—C8 | 1.365 (5) | C21—C22 | 1.374 (6) |
C7—C12 | 1.384 (5) | C21—H21 | 0.9300 |
C8—C9 | 1.394 (5) | C22—C23 | 1.376 (6) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.353 (5) | C23—C24 | 1.386 (5) |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.371 (6) | C24—H24 | 0.9300 |
C10—H10 | 0.9300 | ||
C3—N1—N2 | 103.9 (3) | C10—C11—H11 | 119.4 |
N1—N2—C1 | 112.3 (3) | C12—C11—H11 | 119.4 |
N1—N2—C19 | 118.0 (3) | C11—C12—C7 | 119.5 (4) |
C1—N2—C19 | 129.7 (3) | C11—C12—H12 | 120.2 |
C4—N3—C5 | 118.0 (3) | C7—C12—H12 | 120.2 |
C4—N3—H3 | 121.0 | C14—C13—C18 | 118.5 (3) |
C5—N3—H3 | 121.0 | C14—C13—C1 | 119.2 (3) |
N2—C1—C2 | 106.1 (3) | C18—C13—C1 | 122.3 (3) |
N2—C1—C13 | 122.7 (3) | C15—C14—C13 | 120.7 (4) |
C2—C1—C13 | 131.2 (3) | C15—C14—H14 | 119.7 |
C1—C2—C3 | 105.1 (3) | C13—C14—H14 | 119.7 |
C1—C2—C6 | 127.3 (3) | C16—C15—C14 | 120.0 (4) |
C3—C2—C6 | 127.5 (3) | C16—C15—H15 | 120.0 |
N1—C3—C2 | 112.6 (3) | C14—C15—H15 | 120.0 |
N1—C3—C4 | 119.3 (3) | C15—C16—C17 | 120.6 (4) |
C2—C3—C4 | 127.6 (3) | C15—C16—H16 | 119.7 |
O1—C4—N3 | 124.4 (3) | C17—C16—H16 | 119.7 |
O1—C4—C3 | 121.9 (4) | C18—C17—C16 | 119.7 (4) |
N3—C4—C3 | 113.6 (3) | C18—C17—H17 | 120.2 |
N3—C5—H5A | 109.5 | C16—C17—H17 | 120.2 |
N3—C5—H5B | 109.5 | C17—C18—C13 | 120.6 (4) |
H5A—C5—H5B | 109.5 | C17—C18—H18 | 119.7 |
N3—C5—H5C | 109.5 | C13—C18—H18 | 119.7 |
H5A—C5—H5C | 109.5 | C20—C19—C24 | 121.5 (4) |
H5B—C5—H5C | 109.5 | C20—C19—N2 | 120.0 (3) |
O2—C6—C7 | 121.0 (4) | C24—C19—N2 | 118.5 (3) |
O2—C6—C2 | 119.7 (4) | C19—C20—C21 | 119.0 (4) |
C7—C6—C2 | 119.3 (4) | C19—C20—H20 | 120.5 |
C8—C7—C12 | 119.0 (4) | C21—C20—H20 | 120.5 |
C8—C7—C6 | 122.5 (4) | C22—C21—C20 | 120.3 (4) |
C12—C7—C6 | 118.6 (4) | C22—C21—H21 | 119.8 |
C7—C8—C9 | 121.0 (4) | C20—C21—H21 | 119.8 |
C7—C8—H8 | 119.5 | C21—C22—C23 | 119.9 (4) |
C9—C8—H8 | 119.5 | C21—C22—H22 | 120.1 |
C10—C9—C8 | 119.6 (4) | C23—C22—H22 | 120.1 |
C10—C9—H9 | 120.2 | C22—C23—C24 | 120.6 (4) |
C8—C9—H9 | 120.2 | C22—C23—H23 | 119.7 |
C9—C10—C11 | 119.8 (4) | C24—C23—H23 | 119.7 |
C9—C10—H10 | 120.1 | C19—C24—C23 | 118.7 (4) |
C11—C10—H10 | 120.1 | C19—C24—H24 | 120.7 |
C10—C11—C12 | 121.1 (4) | C23—C24—H24 | 120.7 |
C3—N1—N2—C1 | 0.6 (4) | C6—C7—C8—C9 | 179.4 (4) |
C3—N1—N2—C19 | 178.6 (3) | C7—C8—C9—C10 | 1.2 (7) |
N1—N2—C1—C2 | −0.3 (4) | C8—C9—C10—C11 | −0.5 (7) |
C19—N2—C1—C2 | −178.1 (3) | C9—C10—C11—C12 | 0.4 (7) |
N1—N2—C1—C13 | 179.8 (3) | C10—C11—C12—C7 | −0.9 (7) |
C19—N2—C1—C13 | 2.1 (6) | C8—C7—C12—C11 | 1.5 (6) |
N2—C1—C2—C3 | −0.1 (4) | C6—C7—C12—C11 | −179.6 (4) |
C13—C1—C2—C3 | 179.7 (4) | N2—C1—C13—C14 | −119.5 (4) |
N2—C1—C2—C6 | −177.4 (3) | C2—C1—C13—C14 | 60.7 (6) |
C13—C1—C2—C6 | 2.4 (7) | N2—C1—C13—C18 | 60.8 (5) |
N2—N1—C3—C2 | −0.6 (4) | C2—C1—C13—C18 | −119.0 (4) |
N2—N1—C3—C4 | −173.6 (3) | C18—C13—C14—C15 | 0.2 (6) |
C1—C2—C3—N1 | 0.5 (4) | C1—C13—C14—C15 | −179.5 (4) |
C6—C2—C3—N1 | 177.8 (4) | C13—C14—C15—C16 | 0.1 (6) |
C1—C2—C3—C4 | 172.8 (4) | C14—C15—C16—C17 | −0.3 (6) |
C6—C2—C3—C4 | −9.9 (6) | C15—C16—C17—C18 | 0.1 (7) |
C5—N3—C4—O1 | −2.0 (7) | C16—C17—C18—C13 | 0.2 (6) |
C5—N3—C4—C3 | 178.0 (3) | C14—C13—C18—C17 | −0.4 (6) |
N1—C3—C4—O1 | 150.4 (4) | C1—C13—C18—C17 | 179.3 (3) |
C2—C3—C4—O1 | −21.4 (7) | N1—N2—C19—C20 | −138.7 (4) |
N1—C3—C4—N3 | −29.5 (5) | C1—N2—C19—C20 | 39.0 (6) |
C2—C3—C4—N3 | 158.6 (4) | N1—N2—C19—C24 | 40.1 (5) |
C1—C2—C6—O2 | −54.2 (6) | C1—N2—C19—C24 | −142.2 (4) |
C3—C2—C6—O2 | 129.1 (4) | C24—C19—C20—C21 | 1.9 (6) |
C1—C2—C6—C7 | 127.0 (4) | N2—C19—C20—C21 | −179.3 (3) |
C3—C2—C6—C7 | −49.7 (5) | C19—C20—C21—C22 | −0.8 (6) |
O2—C6—C7—C8 | 165.3 (4) | C20—C21—C22—C23 | −1.1 (7) |
C2—C6—C7—C8 | −15.9 (5) | C21—C22—C23—C24 | 1.9 (7) |
O2—C6—C7—C12 | −13.5 (6) | C20—C19—C24—C23 | −1.0 (6) |
C2—C6—C7—C12 | 165.3 (3) | N2—C19—C24—C23 | −179.8 (4) |
C12—C7—C8—C9 | −1.7 (6) | C22—C23—C24—C19 | −0.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N1 | 0.86 | 2.41 | 2.723 (4) | 102 |
C5—H5A···O2i | 0.96 | 2.56 | 3.506 (5) | 170 |
C10—H10···Cg3ii | 0.93 | 2.83 | 3.659 (4) | 149 |
C8—H8···Cg4iii | 0.93 | 3.06 | 3.816 (4) | 139 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z; (iii) x, −y−1/2, z−3/2. |