Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028733/cf6304sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028733/cf6304IVsup2.hkl |
CCDC reference: 234890
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.079
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H23 .. CG1 = 2.79 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2136 Count of symmetry unique reflns 2159 Completeness (_total/calc) 98.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).
C20H25NO2 | F(000) = 336 |
Mr = 311.41 | Dx = 1.177 Mg m−3 |
Monoclinic, P21 | Melting point: 344 K |
Hall symbol: p_2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2962 (2) Å | Cell parameters from 14364 reflections |
b = 8.2755 (2) Å | θ = 2.6–27.5° |
c = 11.4267 (3) Å | µ = 0.08 mm−1 |
β = 91.0830 (11)° | T = 150 K |
V = 878.91 (4) Å3 | Block, colourless |
Z = 2 | 0.36 × 0.30 × 0.20 mm |
Nonius KappaCCD diffractometer | 1988 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.036 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
φ and ω scans with κ offsets | h = −12→12 |
8081 measured reflections | k = −9→10 |
2136 independent reflections | l = −13→14 |
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)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0392P)2 + 0.0616P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2136 reflections | Δρmax = 0.14 e Å−3 |
212 parameters | Δρmin = −0.11 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.068 (15) |
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. Cambridge Structural search on propoxyaromatic derivatives ———————————————————- Query Refcode ANG1 ANG2 TOR1 1 CIBCOF 114.243 124.847 20.268 1 DOVVEP 115.584 124.952 0.549 1 DOVVEP 116.417 124.358 - 0.309 1 FUNYOC 124.781 116.229 174.433 1 JILVUV 124.992 115.066 176.017 1 JILVUV 125.589 115.823 - 178.477 1 JULTUF 125.077 114.808 175.562 1 JULTUF 125.847 113.872 - 178.221 1 JULTUF 125.668 115.065 - 178.716 1 JULTUF 125.787 115.778 175.458 1 JULTUF01 125.330 115.567 179.724 1 JULTUF01 125.129 115.114 - 174.997 1 JULTUF01 124.846 115.194 - 176.362 1 JULTUF01 125.091 115.457 179.503 1 LONMEG 125.293 115.310 - 174.706 1 LONMIK 116.035 125.107 0.848 1 OCERAP 116.124 124.679 - 5.123 1 PEYGAB 116.025 124.493 - 2.659 1 PIGHUI 115.234 124.913 2.248 1 ZZZLAO10 123.895 115.843 - 179.157 1 XOSKUL 116.515 124.789 - 5.215 1 LUSFIO 115.101 125.458 - 4.903 1 LUSFIO 115.978 125.619 5.761 Specified hydrogen bonds (with e.s.d.'s except fixed and riding H) ————————————————————– D—H H···A D···A <(DHA) 0.95 2.99 3.750 (2) 138.1 C23—H23···C11_$2 0.95 2.95 3.663 (2) 133.0 C23—H23···C12_$2 0.95 3.10 3.884 (2) 141.4 C23—H23···C13_$2 0.95 3.25 4.152 (2) 159.1 C23—H23···C14_$2 0.95 3.26 4.205 (2) 174.3 C23—H23···C15_$2 0.95 3.14 4.017 (2) 155.1 C23—H23···C16_$2 0.95 2.60 3.374 (2) 139.0 C22—H22···O1_$2 Planes data ########### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019) * -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31 Rms deviation of fitted atoms = 0.0032 6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054) Angle to previous plane (with approximate e.s.d.) = 79.14 (5) * 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31 Rms deviation of fitted atoms = 0.0549 7.5676(0.0039)x + 4.7708(0.0049)y - 0.9804(0.0089)z = 7.0274(0.0041) Angle to previous plane (with approximate e.s.d.) = 79.23 (5) * 0.0038(0.0011) C11 * -0.0050(0.0012) C12 * 0.0019(0.0013) C13 * 0.0023(0.0013) C14 * -0.0034(0.0014) C15 * 0.0003(0.0012) C16 - 0.9213(0.0027) O1 1.0898(0.0035) N3 - 3.0060(0.0065) O31 Rms deviation of fitted atoms = 0.0031 5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019) Angle to previous plane (with approximate e.s.d.) = 33.58 (7) * -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31 Rms deviation of fitted atoms = 0.0032 6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054) Angle to previous plane (with approximate e.s.d.)= 79.14 (5) * 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31 Rms deviation of fitted atoms = 0.0549 6.2495(0.0113)x + 4.9688(0.0152)y + 4.8026(0.0106)z = 5.5802(0.0070) Angle to previous plane (with approximate e.s.d.) = 73.35 (10) * 0.0406 (0.0009) O31 * -0.0373 (0.0008) C32 * -0.0429 (0.0009) C33 * 0.0396 (0.0009) C34 0.0867 (0.0057) C21 0.0603 (0.0027) C24 0.0663 (0.0074) C2 - 1.0601 (0.0070) O1 Rms deviation of fitted atoms = 0.0401 5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019) Angle to previous plane (with approximate e.s.d.) = 6.7 (2) * -0.0039 (0.0010) C21 * 0.0037 (0.0011) C22 * 0.0004 (0.0011) C23 * -0.0042 (0.0011) C24 * 0.0040 (0.0012) C25 * 0.0001 (0.0012) C26 - 0.0242 (0.0022) O31 - 1.2464 (0.0025) O1 Rms deviation of fitted atoms = 0.0032 |
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 | 0.62951 (11) | 0.25267 (14) | −0.13941 (9) | 0.0336 (3) | |
C2 | 0.64463 (15) | 0.37668 (18) | −0.05284 (12) | 0.0284 (3) | |
N3 | 0.79419 (13) | 0.42830 (16) | −0.06489 (10) | 0.0298 (3) | |
C31 | 0.82173 (18) | 0.5817 (2) | −0.00494 (14) | 0.0400 (4) | |
C4 | 0.80871 (16) | 0.4413 (2) | −0.19220 (13) | 0.0319 (3) | |
C41 | 0.96437 (19) | 0.4422 (2) | −0.22974 (17) | 0.0447 (4) | |
C5 | 0.71528 (16) | 0.2981 (2) | −0.23745 (13) | 0.0316 (3) | |
C11 | 0.79682 (16) | 0.15241 (19) | −0.27952 (13) | 0.0335 (3) | |
C12 | 0.86946 (17) | 0.0513 (2) | −0.20172 (15) | 0.0384 (4) | |
C13 | 0.9480 (2) | −0.0799 (2) | −0.2413 (2) | 0.0504 (5) | |
C14 | 0.9534 (2) | −0.1127 (3) | −0.3595 (2) | 0.0595 (6) | |
C15 | 0.8799 (2) | −0.0135 (3) | −0.43796 (19) | 0.0602 (6) | |
C16 | 0.80236 (19) | 0.1184 (3) | −0.39881 (14) | 0.0456 (4) | |
C21 | 0.60989 (15) | 0.31007 (18) | 0.06553 (12) | 0.0282 (3) | |
C22 | 0.49376 (16) | 0.36969 (19) | 0.12624 (13) | 0.0296 (3) | |
C23 | 0.45726 (15) | 0.30686 (19) | 0.23513 (13) | 0.0298 (3) | |
C24 | 0.53876 (15) | 0.1832 (2) | 0.28387 (12) | 0.0287 (3) | |
C25 | 0.65725 (16) | 0.1231 (2) | 0.22425 (13) | 0.0345 (3) | |
C26 | 0.69145 (15) | 0.1862 (2) | 0.11617 (13) | 0.0337 (3) | |
O31 | 0.51184 (12) | 0.11104 (15) | 0.38943 (9) | 0.0361 (3) | |
C32 | 0.39621 (16) | 0.1753 (2) | 0.45720 (13) | 0.0327 (3) | |
C33 | 0.38810 (17) | 0.0773 (2) | 0.56802 (14) | 0.0377 (4) | |
C34 | 0.2810 (2) | 0.1468 (3) | 0.65260 (16) | 0.0527 (5) | |
H2 | 0.5785 | 0.4685 | −0.0724 | 0.034* | |
H31A | 0.7556 | 0.6642 | −0.0358 | 0.060* | |
H31B | 0.9212 | 0.6155 | −0.0180 | 0.060* | |
H31C | 0.8068 | 0.5682 | 0.0792 | 0.060* | |
H4 | 0.7625 | 0.5444 | −0.2187 | 0.038* | |
H41A | 1.0110 | 0.5420 | −0.2027 | 0.067* | |
H41B | 0.9681 | 0.4364 | −0.3153 | 0.067* | |
H41C | 1.0146 | 0.3489 | −0.1955 | 0.067* | |
H5 | 0.6503 | 0.3374 | −0.3021 | 0.038* | |
H12 | 0.8655 | 0.0722 | −0.1201 | 0.046* | |
H13 | 0.9980 | −0.1472 | −0.1869 | 0.060* | |
H14 | 1.0070 | −0.2025 | −0.3868 | 0.071* | |
H15 | 0.8828 | −0.0361 | −0.5194 | 0.072* | |
H16 | 0.7528 | 0.1857 | −0.4535 | 0.055* | |
H22 | 0.4379 | 0.4549 | 0.0932 | 0.036* | |
H23 | 0.3770 | 0.3487 | 0.2755 | 0.036* | |
H25 | 0.7142 | 0.0392 | 0.2579 | 0.041* | |
H26 | 0.7718 | 0.1444 | 0.0758 | 0.040* | |
H32A | 0.3043 | 0.1679 | 0.4124 | 0.039* | |
H32B | 0.4146 | 0.2903 | 0.4761 | 0.039* | |
H33A | 0.4844 | 0.0737 | 0.6064 | 0.045* | |
H33B | 0.3599 | −0.0349 | 0.5481 | 0.045* | |
H34A | 0.3124 | 0.2549 | 0.6771 | 0.079* | |
H34B | 0.2752 | 0.0766 | 0.7214 | 0.079* | |
H34C | 0.1861 | 0.1540 | 0.6141 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0342 (5) | 0.0392 (6) | 0.0276 (5) | −0.0073 (5) | 0.0087 (4) | −0.0026 (5) |
C2 | 0.0276 (6) | 0.0318 (7) | 0.0257 (7) | 0.0008 (6) | 0.0025 (5) | 0.0023 (6) |
N3 | 0.0290 (6) | 0.0338 (7) | 0.0268 (6) | −0.0023 (5) | 0.0028 (5) | 0.0027 (5) |
C31 | 0.0463 (9) | 0.0408 (9) | 0.0331 (8) | −0.0092 (7) | 0.0018 (7) | −0.0012 (7) |
C4 | 0.0358 (7) | 0.0310 (7) | 0.0292 (7) | −0.0008 (6) | 0.0073 (6) | 0.0037 (6) |
C41 | 0.0424 (9) | 0.0413 (9) | 0.0510 (10) | −0.0111 (8) | 0.0192 (8) | −0.0065 (8) |
C5 | 0.0314 (7) | 0.0395 (8) | 0.0241 (7) | −0.0035 (6) | 0.0043 (5) | 0.0033 (6) |
C11 | 0.0324 (7) | 0.0373 (9) | 0.0311 (7) | −0.0081 (6) | 0.0059 (6) | −0.0042 (6) |
C12 | 0.0386 (8) | 0.0368 (9) | 0.0401 (9) | −0.0036 (7) | 0.0038 (7) | −0.0027 (7) |
C13 | 0.0457 (10) | 0.0361 (9) | 0.0697 (13) | −0.0018 (8) | 0.0117 (9) | −0.0029 (9) |
C14 | 0.0542 (11) | 0.0425 (11) | 0.0827 (16) | −0.0081 (9) | 0.0286 (11) | −0.0218 (11) |
C15 | 0.0653 (13) | 0.0657 (14) | 0.0504 (12) | −0.0212 (11) | 0.0265 (10) | −0.0249 (10) |
C16 | 0.0475 (9) | 0.0580 (11) | 0.0317 (8) | −0.0128 (8) | 0.0098 (7) | −0.0074 (8) |
C21 | 0.0276 (6) | 0.0299 (7) | 0.0270 (7) | −0.0008 (6) | 0.0014 (5) | 0.0018 (6) |
C22 | 0.0307 (7) | 0.0297 (7) | 0.0284 (7) | 0.0027 (6) | 0.0027 (5) | 0.0031 (6) |
C23 | 0.0301 (7) | 0.0324 (7) | 0.0272 (7) | 0.0026 (6) | 0.0061 (6) | 0.0000 (6) |
C24 | 0.0298 (7) | 0.0327 (7) | 0.0237 (6) | 0.0003 (6) | 0.0034 (5) | 0.0024 (6) |
C25 | 0.0316 (7) | 0.0398 (9) | 0.0322 (8) | 0.0093 (6) | 0.0050 (6) | 0.0083 (7) |
C26 | 0.0294 (7) | 0.0402 (8) | 0.0319 (7) | 0.0067 (6) | 0.0079 (6) | 0.0061 (7) |
O31 | 0.0386 (6) | 0.0433 (7) | 0.0266 (5) | 0.0094 (5) | 0.0106 (4) | 0.0098 (5) |
C32 | 0.0336 (7) | 0.0370 (8) | 0.0279 (7) | 0.0021 (6) | 0.0083 (6) | 0.0005 (6) |
C33 | 0.0397 (8) | 0.0431 (9) | 0.0307 (8) | −0.0020 (7) | 0.0080 (6) | 0.0063 (7) |
C34 | 0.0626 (11) | 0.0601 (12) | 0.0362 (9) | −0.0003 (10) | 0.0211 (8) | 0.0056 (8) |
O1—C2 | 1.4305 (18) | C2—H2 | 1.000 |
O1—C5 | 1.4373 (17) | C31—H31A | 0.980 |
C2—N3 | 1.4635 (18) | C31—H31B | 0.980 |
C2—C21 | 1.5014 (19) | C31—H31C | 0.980 |
N3—C31 | 1.463 (2) | C4—H4 | 1.000 |
N3—C4 | 1.4676 (18) | C41—H41A | 0.980 |
C4—C41 | 1.517 (2) | C41—H41B | 0.980 |
C4—C5 | 1.552 (2) | C41—H41C | 0.980 |
C5—C11 | 1.508 (2) | C5—H5 | 1.000 |
C11—C12 | 1.387 (2) | C12—H12 | 0.950 |
C11—C16 | 1.394 (2) | C13—H13 | 0.950 |
C12—C13 | 1.389 (3) | C14—H14 | 0.950 |
C13—C14 | 1.379 (3) | C15—H15 | 0.950 |
C14—C15 | 1.386 (3) | C16—H16 | 0.950 |
C15—C16 | 1.387 (3) | C22—H22 | 0.950 |
C21—C22 | 1.385 (2) | C23—H23 | 0.950 |
C21—C26 | 1.394 (2) | C25—H25 | 0.950 |
C22—C23 | 1.396 (2) | C26—H26 | 0.950 |
C23—C24 | 1.384 (2) | C32—H32A | 0.990 |
C24—O31 | 1.3731 (17) | C32—H32B | 0.990 |
C24—C25 | 1.398 (2) | C33—H33A | 0.990 |
C25—C26 | 1.383 (2) | C33—H33B | 0.990 |
O31—C32 | 1.4386 (17) | C34—H34A | 0.980 |
C32—C33 | 1.507 (2) | C34—H34B | 0.980 |
C33—C34 | 1.514 (2) | C34—H34C | 0.980 |
C2—O1—C5 | 107.60 (11) | C5—C4—H4 | 108.4 |
O1—C2—N3 | 103.03 (11) | C4—C41—H41A | 109.5 |
O1—C2—C21 | 109.85 (12) | C4—C41—H41B | 109.5 |
N3—C2—C21 | 114.38 (12) | H41A—C41—H41B | 109.5 |
C31—N3—C2 | 111.56 (12) | C4—C41—H41C | 109.5 |
C31—N3—C4 | 112.46 (12) | H41A—C41—H41C | 109.5 |
C2—N3—C4 | 102.71 (11) | H41B—C41—H41C | 109.5 |
N3—C4—C41 | 112.76 (13) | O1—C5—H5 | 108.9 |
N3—C4—C5 | 102.30 (11) | C11—C5—H5 | 108.9 |
C41—C4—C5 | 116.15 (14) | C4—C5—H5 | 108.9 |
O1—C5—C11 | 109.19 (12) | C11—C12—H12 | 119.5 |
O1—C5—C4 | 104.80 (12) | C13—C12—H12 | 119.5 |
C11—C5—C4 | 115.79 (12) | C14—C13—H13 | 119.9 |
C12—C11—C16 | 118.58 (16) | C12—C13—H13 | 119.9 |
C12—C11—C5 | 121.31 (14) | C13—C14—H14 | 120.3 |
C16—C11—C5 | 120.10 (15) | C15—C14—H14 | 120.3 |
C11—C12—C13 | 121.01 (17) | C14—C15—H15 | 119.7 |
C14—C13—C12 | 120.1 (2) | C16—C15—H15 | 119.7 |
C13—C14—C15 | 119.34 (19) | C15—C16—H16 | 119.9 |
C14—C15—C16 | 120.68 (19) | C11—C16—H16 | 119.9 |
C15—C16—C11 | 120.2 (2) | C21—C22—H22 | 119.4 |
C22—C21—C26 | 118.49 (13) | C23—C22—H22 | 119.4 |
C22—C21—C2 | 120.22 (13) | C24—C23—H23 | 120.2 |
C26—C21—C2 | 121.28 (13) | C22—C23—H23 | 120.2 |
C21—C22—C23 | 121.23 (14) | C26—C25—H25 | 120.1 |
C24—C23—C22 | 119.58 (13) | C24—C25—H25 | 120.1 |
O31—C24—C23 | 124.58 (13) | C25—C26—H26 | 119.5 |
O31—C24—C25 | 115.60 (13) | C21—C26—H26 | 119.5 |
C23—C24—C25 | 119.82 (13) | O31—C32—H32A | 110.2 |
C26—C25—C24 | 119.85 (14) | C33—C32—H32A | 110.2 |
C25—C26—C21 | 121.03 (14) | O31—C32—H32B | 110.2 |
C24—O31—C32 | 117.55 (12) | C33—C32—H32B | 110.2 |
O31—C32—C33 | 107.64 (13) | H32A—C32—H32B | 108.5 |
C32—C33—C34 | 112.06 (15) | C32—C33—H33A | 109.2 |
O1—C2—H2 | 109.8 | C34—C33—H33A | 109.2 |
N3—C2—H2 | 109.8 | C32—C33—H33B | 109.2 |
C21—C2—H2 | 109.8 | C34—C33—H33B | 109.2 |
N3—C31—H31A | 109.5 | H33A—C33—H33B | 107.9 |
N3—C31—H31B | 109.5 | C33—C34—H34A | 109.5 |
H31A—C31—H31B | 109.5 | C33—C34—H34B | 109.5 |
N3—C31—H31C | 109.5 | H34A—C34—H34B | 109.5 |
H31A—C31—H31C | 109.5 | C33—C34—H34C | 109.5 |
H31B—C31—H31C | 109.5 | H34A—C34—H34C | 109.5 |
N3—C4—H4 | 108.4 | H34B—C34—H34C | 109.5 |
C41—C4—H4 | 108.4 | ||
C5—O1—C2—N3 | −35.09 (14) | C12—C13—C14—C15 | 0.0 (3) |
C5—O1—C2—C21 | −157.36 (12) | C13—C14—C15—C16 | 0.5 (3) |
O1—C2—N3—C31 | 165.60 (11) | C14—C15—C16—C11 | −0.3 (3) |
C21—C2—N3—C31 | −75.22 (16) | C12—C11—C16—C15 | −0.4 (2) |
O1—C2—N3—C4 | 44.92 (14) | C5—C11—C16—C15 | 178.55 (16) |
C21—C2—N3—C4 | 164.10 (13) | O1—C2—C21—C22 | −116.58 (15) |
C31—N3—C4—C41 | 77.85 (18) | N3—C2—C21—C22 | 128.16 (15) |
C2—N3—C4—C41 | −162.09 (14) | O1—C2—C21—C26 | 62.48 (17) |
C31—N3—C4—C5 | −156.66 (12) | N3—C2—C21—C26 | −52.78 (19) |
C2—N3—C4—C5 | −36.61 (14) | C26—C21—C22—C23 | −0.7 (2) |
C2—O1—C5—C11 | 136.36 (12) | C2—C21—C22—C23 | 178.39 (14) |
C2—O1—C5—C4 | 11.71 (15) | C21—C22—C23—C24 | 0.3 (2) |
N3—C4—C5—O1 | 15.80 (15) | C22—C23—C24—O31 | −179.17 (14) |
C41—C4—C5—O1 | 139.03 (14) | C22—C23—C24—C25 | 0.5 (2) |
N3—C4—C5—C11 | −104.55 (14) | O31—C24—C25—C26 | 178.86 (15) |
C41—C4—C5—C11 | 18.68 (19) | C23—C24—C25—C26 | −0.8 (2) |
O1—C5—C11—C12 | −46.28 (18) | C24—C25—C26—C21 | 0.4 (3) |
C4—C5—C11—C12 | 71.67 (18) | C22—C21—C26—C25 | 0.4 (2) |
O1—C5—C11—C16 | 134.80 (14) | C2—C21—C26—C25 | −178.72 (15) |
C4—C5—C11—C16 | −107.25 (16) | C23—C24—O31—C32 | −4.0 (2) |
C16—C11—C12—C13 | 0.9 (2) | C25—C24—O31—C32 | 176.37 (14) |
C5—C11—C12—C13 | −178.03 (15) | C24—O31—C32—C33 | −179.93 (13) |
C11—C12—C13—C14 | −0.7 (3) | O31—C32—C33—C34 | 173.36 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O1i | 0.95 | 2.60 | 3.3745 (19) | 139 |
C23—H23···Cg1i | 0.95 | 2.79 | 3.6987 (16) | 161 |
Symmetry code: (i) −x+1, y+1/2, −z. |