Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023050/ww6292sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023050/ww6292Isup2.hkl |
CCDC reference: 253021
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.085
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H17N3O3 | F(000) = 824 |
Mr = 395.41 | Dx = 1.379 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4211 reflections |
a = 8.9688 (5) Å | θ = 1.9–27.3° |
b = 10.9081 (4) Å | µ = 0.09 mm−1 |
c = 19.8159 (11) Å | T = 150 K |
β = 100.841 (4)° | Plate, yellow |
V = 1904.04 (17) Å3 | 0.58 × 0.40 × 0.16 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 4211 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3172 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.038 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 2.1° |
ω scans | h = −11→11 |
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.955, Tmax = 0.985 | l = −25→25 |
29930 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)] = 0.032 | All H-atom parameters refined |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.0168P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4211 reflections | Δρmax = 0.18 e Å−3 |
340 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0145 (13) |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.85676 (9) | 0.62582 (7) | 0.14423 (5) | 0.0418 (3) | |
O2 | 0.50863 (10) | 0.79559 (7) | 0.30215 (4) | 0.0409 (3) | |
O3 | 0.51146 (9) | 0.64217 (7) | 0.00892 (4) | 0.0340 (2) | |
N1 | 0.67126 (10) | 0.49045 (9) | 0.10232 (5) | 0.0314 (3) | |
N2 | 0.56556 (10) | 0.57348 (8) | 0.11919 (5) | 0.0293 (3) | |
N3 | 0.38932 (10) | 0.73350 (8) | 0.08702 (5) | 0.0301 (3) | |
C1 | 0.93002 (12) | 0.44978 (10) | 0.08708 (6) | 0.0313 (3) | |
C2 | 1.08293 (14) | 0.48082 (12) | 0.10497 (7) | 0.0413 (4) | |
C3 | 1.19166 (14) | 0.41050 (12) | 0.08226 (8) | 0.0453 (4) | |
C4 | 1.14950 (14) | 0.31089 (11) | 0.04040 (7) | 0.0412 (4) | |
C5 | 0.99821 (15) | 0.27883 (12) | 0.02245 (7) | 0.0436 (4) | |
C6 | 0.88851 (13) | 0.34726 (11) | 0.04636 (6) | 0.0383 (4) | |
C7 | 0.81985 (12) | 0.53149 (10) | 0.11268 (6) | 0.0315 (3) | |
C8 | 0.55249 (12) | 0.58260 (10) | 0.18591 (6) | 0.0303 (3) | |
C9 | 0.45887 (12) | 0.66850 (10) | 0.20525 (6) | 0.0295 (3) | |
C10 | 0.46216 (12) | 0.69555 (10) | 0.28015 (6) | 0.0306 (3) | |
C11 | 0.40679 (12) | 0.60336 (10) | 0.32422 (6) | 0.0309 (3) | |
C12 | 0.35090 (12) | 0.48935 (10) | 0.29950 (6) | 0.0337 (3) | |
C13 | 0.29858 (14) | 0.40736 (12) | 0.34322 (7) | 0.0427 (4) | |
C14 | 0.29861 (17) | 0.44028 (14) | 0.41039 (8) | 0.0532 (5) | |
C15 | 0.35242 (18) | 0.55333 (14) | 0.43505 (8) | 0.0530 (5) | |
C16 | 0.40732 (15) | 0.63468 (12) | 0.39257 (6) | 0.0406 (4) | |
C17 | 0.37499 (11) | 0.74296 (10) | 0.15193 (6) | 0.0290 (3) | |
C18 | 0.26569 (12) | 0.83595 (10) | 0.16714 (6) | 0.0306 (3) | |
C19 | 0.17098 (12) | 0.81260 (11) | 0.21388 (6) | 0.0355 (3) | |
C20 | 0.07216 (14) | 0.90172 (13) | 0.22835 (7) | 0.0423 (4) | |
C21 | 0.06821 (15) | 1.01514 (13) | 0.19706 (7) | 0.0463 (4) | |
C22 | 0.16080 (15) | 1.03925 (12) | 0.15042 (7) | 0.0439 (4) | |
C23 | 0.25845 (13) | 0.94976 (11) | 0.13456 (6) | 0.0358 (3) | |
C24 | 0.48910 (11) | 0.65173 (10) | 0.06797 (5) | 0.0292 (3) | |
H1 | 0.6324 (17) | 0.4439 (13) | 0.0661 (8) | 0.046 (4)* | |
H2 | 1.1109 (17) | 0.5564 (14) | 0.1362 (8) | 0.055 (4)* | |
H3 | 1.2977 (18) | 0.4316 (14) | 0.0962 (8) | 0.057 (4)* | |
H4 | 1.2265 (17) | 0.2618 (13) | 0.0215 (8) | 0.052 (4)* | |
H5 | 0.9661 (16) | 0.2080 (14) | −0.0076 (8) | 0.053 (4)* | |
H6 | 0.7820 (16) | 0.3241 (12) | 0.0330 (7) | 0.044 (4)* | |
H8 | 0.6153 (14) | 0.5256 (11) | 0.2173 (7) | 0.033 (3)* | |
H12 | 0.3487 (14) | 0.4633 (12) | 0.2511 (7) | 0.040 (3)* | |
H13 | 0.2583 (15) | 0.3283 (14) | 0.3261 (7) | 0.047 (4)* | |
H14 | 0.2595 (19) | 0.3819 (15) | 0.4406 (9) | 0.065 (5)* | |
H15 | 0.354 (2) | 0.5763 (16) | 0.4826 (9) | 0.072 (5)* | |
H16 | 0.4509 (17) | 0.7166 (15) | 0.4092 (8) | 0.059 (4)* | |
H19 | 0.1726 (14) | 0.7301 (12) | 0.2357 (7) | 0.039 (3)* | |
H20 | 0.0047 (17) | 0.8817 (13) | 0.2613 (8) | 0.052 (4)* | |
H21 | 0.0019 (17) | 1.0821 (15) | 0.2075 (8) | 0.058 (4)* | |
H22 | 0.1636 (17) | 1.1216 (15) | 0.1289 (8) | 0.057 (4)* | |
H23 | 0.3284 (15) | 0.9652 (12) | 0.1018 (7) | 0.039 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0381 (4) | 0.0358 (5) | 0.0523 (5) | −0.0030 (3) | 0.0107 (4) | −0.0107 (4) |
O2 | 0.0515 (5) | 0.0348 (4) | 0.0364 (5) | −0.0071 (4) | 0.0084 (4) | −0.0047 (4) |
O3 | 0.0376 (4) | 0.0379 (4) | 0.0272 (4) | −0.0007 (3) | 0.0082 (3) | −0.0016 (3) |
N1 | 0.0299 (4) | 0.0328 (5) | 0.0319 (5) | 0.0028 (4) | 0.0072 (4) | −0.0046 (4) |
N2 | 0.0293 (4) | 0.0306 (5) | 0.0285 (5) | 0.0026 (3) | 0.0066 (3) | −0.0009 (4) |
N3 | 0.0302 (4) | 0.0315 (5) | 0.0287 (5) | −0.0005 (4) | 0.0058 (4) | −0.0006 (4) |
C1 | 0.0330 (5) | 0.0319 (6) | 0.0293 (6) | 0.0022 (4) | 0.0066 (4) | 0.0037 (4) |
C2 | 0.0364 (6) | 0.0383 (6) | 0.0504 (8) | −0.0033 (5) | 0.0115 (5) | −0.0034 (6) |
C3 | 0.0334 (6) | 0.0439 (7) | 0.0606 (9) | −0.0015 (5) | 0.0142 (6) | 0.0011 (6) |
C4 | 0.0420 (6) | 0.0405 (7) | 0.0441 (7) | 0.0102 (5) | 0.0155 (5) | 0.0057 (5) |
C5 | 0.0443 (7) | 0.0425 (7) | 0.0433 (7) | 0.0080 (5) | 0.0065 (5) | −0.0074 (6) |
C6 | 0.0340 (6) | 0.0394 (6) | 0.0400 (7) | 0.0033 (5) | 0.0031 (5) | −0.0049 (5) |
C7 | 0.0334 (5) | 0.0309 (6) | 0.0302 (6) | 0.0002 (4) | 0.0062 (4) | 0.0011 (4) |
C8 | 0.0319 (5) | 0.0311 (5) | 0.0277 (6) | −0.0012 (4) | 0.0049 (4) | 0.0004 (4) |
C9 | 0.0310 (5) | 0.0297 (5) | 0.0284 (5) | −0.0029 (4) | 0.0068 (4) | −0.0004 (4) |
C10 | 0.0319 (5) | 0.0296 (5) | 0.0300 (6) | 0.0024 (4) | 0.0053 (4) | −0.0017 (4) |
C11 | 0.0321 (5) | 0.0317 (5) | 0.0295 (6) | 0.0050 (4) | 0.0077 (4) | 0.0019 (4) |
C12 | 0.0335 (5) | 0.0314 (6) | 0.0370 (7) | 0.0042 (4) | 0.0084 (5) | 0.0030 (5) |
C13 | 0.0397 (6) | 0.0347 (6) | 0.0556 (8) | 0.0043 (5) | 0.0137 (6) | 0.0112 (6) |
C14 | 0.0590 (8) | 0.0532 (8) | 0.0529 (9) | 0.0121 (7) | 0.0245 (7) | 0.0234 (7) |
C15 | 0.0709 (9) | 0.0575 (9) | 0.0348 (7) | 0.0142 (7) | 0.0210 (7) | 0.0105 (6) |
C16 | 0.0505 (7) | 0.0419 (7) | 0.0296 (6) | 0.0088 (5) | 0.0083 (5) | 0.0005 (5) |
C17 | 0.0283 (5) | 0.0287 (5) | 0.0299 (6) | −0.0047 (4) | 0.0056 (4) | −0.0009 (4) |
C18 | 0.0292 (5) | 0.0325 (6) | 0.0292 (6) | −0.0005 (4) | 0.0030 (4) | −0.0032 (4) |
C19 | 0.0320 (5) | 0.0392 (6) | 0.0360 (6) | 0.0007 (5) | 0.0082 (5) | −0.0006 (5) |
C20 | 0.0346 (6) | 0.0520 (8) | 0.0413 (7) | 0.0046 (5) | 0.0095 (5) | −0.0055 (6) |
C21 | 0.0402 (7) | 0.0472 (7) | 0.0500 (8) | 0.0123 (6) | 0.0047 (6) | −0.0080 (6) |
C22 | 0.0470 (7) | 0.0358 (7) | 0.0462 (8) | 0.0077 (5) | 0.0021 (6) | 0.0007 (6) |
C23 | 0.0377 (6) | 0.0357 (6) | 0.0330 (6) | 0.0018 (5) | 0.0042 (5) | 0.0004 (5) |
C24 | 0.0291 (5) | 0.0305 (5) | 0.0276 (6) | −0.0033 (4) | 0.0043 (4) | −0.0005 (4) |
O1—C7 | 1.2171 (14) | C14—C15 | 1.380 (2) |
O2—C10 | 1.2191 (13) | C15—C16 | 1.376 (2) |
O3—C24 | 1.2282 (13) | C17—C18 | 1.4805 (15) |
N1—N2 | 1.3964 (13) | C18—C23 | 1.3952 (16) |
N1—C7 | 1.3841 (14) | C18—C19 | 1.3929 (16) |
N2—C8 | 1.3528 (15) | C19—C20 | 1.3814 (18) |
N2—C24 | 1.4026 (14) | C20—C21 | 1.381 (2) |
N3—C17 | 1.3205 (15) | C21—C22 | 1.3790 (19) |
N3—C24 | 1.3660 (14) | C22—C23 | 1.3865 (18) |
N1—H1 | 0.895 (15) | C2—H2 | 1.033 (16) |
C1—C2 | 1.3922 (17) | C3—H3 | 0.967 (16) |
C1—C6 | 1.3883 (16) | C4—H4 | 1.001 (15) |
C1—C7 | 1.4888 (16) | C5—H5 | 0.985 (15) |
C2—C3 | 1.3809 (19) | C6—H6 | 0.975 (14) |
C3—C4 | 1.3761 (19) | C8—H8 | 0.979 (13) |
C4—C5 | 1.3815 (19) | C12—H12 | 0.997 (14) |
C5—C6 | 1.3875 (18) | C13—H13 | 0.971 (15) |
C8—C9 | 1.3605 (16) | C14—H14 | 0.983 (17) |
C9—C10 | 1.5081 (16) | C15—H15 | 0.973 (18) |
C9—C17 | 1.4293 (16) | C16—H16 | 1.006 (16) |
C10—C11 | 1.4777 (16) | C19—H19 | 0.997 (13) |
C11—C16 | 1.3960 (17) | C20—H20 | 0.994 (16) |
C11—C12 | 1.3948 (16) | C21—H21 | 0.988 (16) |
C12—C13 | 1.3869 (17) | C22—H22 | 0.997 (16) |
C13—C14 | 1.379 (2) | C23—H23 | 0.998 (14) |
O1···N2 | 2.6279 (12) | C23···C11i | 3.4009 (16) |
O1···C8 | 3.0330 (14) | C23···C12i | 3.5281 (16) |
O1···C24 | 3.3708 (13) | C24···O1 | 3.3708 (13) |
O1···C13i | 3.4007 (15) | C1···H20ii | 3.043 (16) |
O1···C21ii | 3.3174 (17) | C2···H20ii | 3.097 (15) |
O2···C8i | 3.1948 (13) | C4···H22xii | 2.697 (16) |
O2···C18 | 3.1474 (14) | C5···H22xii | 2.901 (16) |
O2···C19 | 3.2050 (14) | C6···H1 | 2.623 (15) |
O2···C12i | 3.3266 (14) | C7···H8 | 3.016 (13) |
O3···C4iii | 3.4032 (15) | C8···H12 | 2.755 (13) |
O3···C16iv | 3.3620 (15) | C8···H3vii | 3.093 (16) |
O3···O3v | 3.1241 (11) | C9···H19 | 2.827 (13) |
O3···N1v | 2.8772 (13) | C9···H12 | 2.674 (13) |
O3···C7 | 3.3461 (14) | C10···H19 | 2.608 (13) |
O3···N1 | 2.6871 (13) | C11···H23ii | 2.958 (14) |
O1···H13i | 2.553 (15) | C11···H19 | 2.831 (13) |
O1···H2 | 2.435 (16) | C16···H23ii | 2.992 (14) |
O2···H12i | 2.570 (13) | C17···H2vii | 3.094 (15) |
O2···H16 | 2.434 (16) | C20···H13xi | 3.064 (14) |
O2···H3vi | 2.821 (16) | C21···H8i | 3.023 (13) |
O2···H8i | 2.742 (12) | C22···H8i | 2.991 (14) |
O3···H1v | 2.009 (15) | C23···H8i | 3.055 (14) |
O3···H4iii | 2.742 (15) | C24···H3vii | 3.064 (16) |
O3···H6v | 2.633 (14) | C24···H1v | 2.871 (15) |
O3···H1 | 2.584 (15) | C24···H6v | 2.856 (14) |
O3···H16iv | 2.484 (16) | H1···O3 | 2.584 (15) |
N1···O3 | 2.6871 (13) | H1···C6 | 2.623 (15) |
N1···O3v | 2.8772 (13) | H1···H6 | 2.07 (2) |
N2···O1 | 2.6279 (12) | H1···O3v | 2.009 (15) |
N3···C6v | 3.3902 (15) | H1···C24v | 2.871 (15) |
N3···C13i | 3.4478 (16) | H2···O1 | 2.435 (16) |
N1···H6 | 2.584 (14) | H2···C17xiii | 3.094 (15) |
N2···H3vii | 2.822 (16) | H3···N2xiii | 2.822 (16) |
N3···H23 | 2.614 (13) | H3···C8xiii | 3.093 (16) |
N3···H6v | 2.653 (14) | H3···C24xiii | 3.064 (16) |
N3···H15iv | 2.905 (18) | H3···O2xiv | 2.821 (16) |
C2···C6iii | 3.5866 (18) | H4···O3iii | 2.742 (15) |
C4···O3iii | 3.4032 (15) | H4···H14xv | 2.30 (2) |
C4···C7iii | 3.5422 (18) | H6···N1 | 2.584 (14) |
C6···C2iii | 3.5866 (18) | H6···H1 | 2.07 (2) |
C6···N3v | 3.3902 (15) | H6···O3v | 2.633 (15) |
C7···O3 | 3.3461 (14) | H6···N3v | 2.653 (14) |
C7···C4iii | 3.5422 (18) | H6···C24v | 2.856 (14) |
C7···C20ii | 3.4231 (18) | H8···C7 | 3.016 (13) |
C8···O1 | 3.0330 (14) | H8···O2ii | 2.742 (12) |
C8···O2ii | 3.1948 (13) | H8···C21ii | 3.023 (13) |
C8···C12 | 3.3017 (16) | H8···C22ii | 2.991 (13) |
C10···C19 | 2.9807 (16) | H8···C23ii | 3.055 (14) |
C11···C23ii | 3.4009 (16) | H12···C8 | 2.755 (13) |
C11···C19 | 3.5670 (16) | H12···C9 | 2.674 (13) |
C12···C23ii | 3.5281 (16) | H12···O2ii | 2.570 (13) |
C12···O2ii | 3.3266 (14) | H13···O1ii | 2.553 (15) |
C12···C8 | 3.3017 (16) | H13···C20viii | 3.064 (14) |
C13···C17ii | 3.4192 (17) | H14···H4xvi | 2.30 (2) |
C13···C21viii | 3.4429 (19) | H15···N3x | 2.905 (17) |
C13···C20viii | 3.3612 (18) | H15···H23x | 2.46 (2) |
C13···O1ii | 3.4007 (15) | H16···O2 | 2.434 (16) |
C13···N3ii | 3.4478 (16) | H16···O3x | 2.484 (16) |
C15···C15ix | 3.525 (2) | H19···C9 | 2.827 (13) |
C16···O3x | 3.3620 (15) | H19···C10 | 2.608 (13) |
C17···C13i | 3.4192 (17) | H19···C11 | 2.831 (13) |
C18···O2 | 3.1474 (14) | H20···C1i | 3.043 (16) |
C19···C10 | 2.9807 (16) | H20···C2i | 3.097 (15) |
C19···O2 | 3.2050 (14) | H22···C4xvii | 2.697 (16) |
C19···C11 | 3.5670 (16) | H22···C5xvii | 2.901 (16) |
C20···C13xi | 3.3612 (18) | H23···N3 | 2.614 (13) |
C20···C7i | 3.4231 (18) | H23···C11i | 2.958 (14) |
C21···C13xi | 3.4429 (19) | H23···C16i | 2.992 (14) |
C21···O1i | 3.3174 (17) | H23···H15iv | 2.46 (2) |
N2—N1—C7 | 115.65 (9) | C19—C20—C21 | 120.03 (12) |
N1—N2—C8 | 117.98 (9) | C20—C21—C22 | 120.25 (13) |
N1—N2—C24 | 118.88 (9) | C21—C22—C23 | 120.22 (12) |
C8—N2—C24 | 122.82 (9) | C18—C23—C22 | 119.87 (11) |
C17—N3—C24 | 120.60 (9) | N2—C24—N3 | 117.00 (9) |
C7—N1—H1 | 121.4 (10) | O3—C24—N2 | 119.51 (10) |
N2—N1—H1 | 112.4 (10) | O3—C24—N3 | 123.47 (10) |
C2—C1—C7 | 116.92 (10) | C1—C2—H2 | 117.6 (9) |
C2—C1—C6 | 119.18 (11) | C3—C2—H2 | 122.1 (9) |
C6—C1—C7 | 123.90 (10) | C2—C3—H3 | 119.5 (9) |
C1—C2—C3 | 120.27 (12) | C4—C3—H3 | 120.3 (9) |
C2—C3—C4 | 120.28 (12) | C3—C4—H4 | 121.2 (9) |
C3—C4—C5 | 120.02 (12) | C5—C4—H4 | 118.8 (9) |
C4—C5—C6 | 120.08 (12) | C4—C5—H5 | 121.0 (9) |
C1—C6—C5 | 120.13 (11) | C6—C5—H5 | 118.9 (9) |
O1—C7—N1 | 120.72 (10) | C1—C6—H6 | 120.6 (8) |
N1—C7—C1 | 115.98 (10) | C5—C6—H6 | 119.3 (8) |
O1—C7—C1 | 123.18 (10) | N2—C8—H8 | 115.4 (8) |
N2—C8—C9 | 119.83 (10) | C9—C8—H8 | 124.8 (8) |
C8—C9—C17 | 116.75 (10) | C11—C12—H12 | 122.2 (8) |
C10—C9—C17 | 121.77 (10) | C13—C12—H12 | 118.0 (8) |
C8—C9—C10 | 120.87 (10) | C12—C13—H13 | 120.1 (8) |
C9—C10—C11 | 120.13 (10) | C14—C13—H13 | 120.1 (8) |
O2—C10—C9 | 117.98 (10) | C13—C14—H14 | 119.0 (10) |
O2—C10—C11 | 121.88 (10) | C15—C14—H14 | 120.3 (10) |
C12—C11—C16 | 119.63 (11) | C14—C15—H15 | 120.9 (10) |
C10—C11—C12 | 122.53 (10) | C16—C15—H15 | 119.0 (10) |
C10—C11—C16 | 117.82 (10) | C11—C16—H16 | 117.8 (9) |
C11—C12—C13 | 119.81 (11) | C15—C16—H16 | 122.3 (9) |
C12—C13—C14 | 119.77 (12) | C18—C19—H19 | 119.5 (8) |
C13—C14—C15 | 120.75 (14) | C20—C19—H19 | 120.2 (8) |
C14—C15—C16 | 120.08 (14) | C19—C20—H20 | 118.4 (8) |
C11—C16—C15 | 119.95 (12) | C21—C20—H20 | 121.6 (8) |
C9—C17—C18 | 121.03 (10) | C20—C21—H21 | 122.3 (9) |
N3—C17—C18 | 116.19 (10) | C22—C21—H21 | 117.5 (9) |
N3—C17—C9 | 122.79 (10) | C21—C22—H22 | 121.7 (9) |
C17—C18—C19 | 121.34 (10) | C23—C22—H22 | 118.0 (9) |
C17—C18—C23 | 119.37 (10) | C18—C23—H23 | 118.1 (8) |
C19—C18—C23 | 119.29 (10) | C22—C23—H23 | 122.0 (8) |
C18—C19—C20 | 120.31 (11) | ||
C7—N1—N2—C8 | −81.78 (12) | C10—C9—C17—C18 | −11.22 (16) |
C7—N1—N2—C24 | 92.00 (12) | C8—C9—C17—C18 | 177.70 (10) |
N2—N1—C7—C1 | −172.91 (9) | C8—C9—C10—O2 | 112.40 (13) |
N2—N1—C7—O1 | 10.85 (16) | C17—C9—C10—C11 | 120.27 (12) |
N1—N2—C24—N3 | −178.50 (9) | C10—C9—C17—N3 | 168.89 (10) |
C24—N2—C8—C9 | 1.77 (16) | C8—C9—C17—N3 | −2.20 (16) |
C8—N2—C24—O3 | 176.62 (10) | C9—C10—C11—C16 | −177.78 (11) |
C8—N2—C24—N3 | −5.04 (15) | O2—C10—C11—C16 | 0.76 (17) |
N1—N2—C24—O3 | 3.16 (15) | O2—C10—C11—C12 | 178.88 (11) |
N1—N2—C8—C9 | 175.29 (10) | C9—C10—C11—C12 | 0.35 (16) |
C17—N3—C24—O3 | −177.13 (10) | C10—C11—C12—C13 | −179.10 (11) |
C24—N3—C17—C18 | 178.95 (9) | C10—C11—C16—C15 | 177.98 (12) |
C17—N3—C24—N2 | 4.60 (15) | C12—C11—C16—C15 | −0.21 (19) |
C24—N3—C17—C9 | −1.15 (16) | C16—C11—C12—C13 | −1.01 (17) |
C2—C1—C7—N1 | −171.63 (11) | C11—C12—C13—C14 | 1.63 (19) |
C7—C1—C6—C5 | 177.43 (11) | C12—C13—C14—C15 | −1.0 (2) |
C2—C1—C7—O1 | 4.51 (18) | C13—C14—C15—C16 | −0.2 (2) |
C7—C1—C2—C3 | −179.01 (12) | C14—C15—C16—C11 | 0.8 (2) |
C6—C1—C7—O1 | −174.62 (12) | N3—C17—C18—C23 | −40.68 (15) |
C2—C1—C6—C5 | −1.69 (18) | C9—C17—C18—C19 | −39.91 (16) |
C6—C1—C2—C3 | 0.17 (19) | C9—C17—C18—C23 | 139.41 (11) |
C6—C1—C7—N1 | 9.24 (17) | N3—C17—C18—C19 | 140.00 (11) |
C1—C2—C3—C4 | 1.6 (2) | C19—C18—C23—C22 | 1.87 (18) |
C2—C3—C4—C5 | −1.8 (2) | C23—C18—C19—C20 | −0.71 (18) |
C3—C4—C5—C6 | 0.3 (2) | C17—C18—C19—C20 | 178.62 (11) |
C4—C5—C6—C1 | 1.49 (19) | C17—C18—C23—C22 | −177.47 (11) |
N2—C8—C9—C10 | −169.35 (10) | C18—C19—C20—C21 | −0.79 (19) |
N2—C8—C9—C17 | 1.82 (16) | C19—C20—C21—C22 | 1.1 (2) |
C8—C9—C10—C11 | −69.01 (14) | C20—C21—C22—C23 | 0.1 (2) |
C17—C9—C10—O2 | −58.32 (15) | C21—C22—C23—C18 | −1.55 (19) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z; (iv) x, −y+3/2, z−1/2; (v) −x+1, −y+1, −z; (vi) −x+2, y+1/2, −z+1/2; (vii) x−1, y, z; (viii) −x, y−1/2, −z+1/2; (ix) −x+1, −y+1, −z+1; (x) x, −y+3/2, z+1/2; (xi) −x, y+1/2, −z+1/2; (xii) x+1, y−1, z; (xiii) x+1, y, z; (xiv) −x+2, y−1/2, −z+1/2; (xv) x+1, −y+1/2, z−1/2; (xvi) x−1, −y+1/2, z+1/2; (xvii) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3v | 0.895 (15) | 2.009 (15) | 2.8772 (13) | 163.4 (14) |
C12—H12···O2ii | 0.997 (14) | 2.570 (13) | 3.3266 (14) | 132.6 (10) |
C13—H13···O1ii | 0.971 (15) | 2.553 (15) | 3.4007 (15) | 145.9 (11) |
C16—H16···O3x | 1.006 (16) | 2.484 (16) | 3.3620 (15) | 145.6 (12) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (v) −x+1, −y+1, −z; (x) x, −y+3/2, z+1/2. |