Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199014032/na0100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014032/na01001sup2.fcf | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014032/na01002sup3.fcf |
CCDC references: 144372; 144373
For both compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1999); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C24H40N6·2(C12H9O4S) | F(000) = 1936 |
Mr = 911.12 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 18.0527 (5) Å | Cell parameters from 9421 reflections |
b = 13.1074 (2) Å | θ = 4.1–26.3° |
c = 20.5723 (5) Å | µ = 0.18 mm−1 |
β = 108.2524 (11)° | T = 100 K |
V = 4622.97 (18) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.34 × 0.31 mm |
Kappa-CCD diffractometer | 9421 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 6549 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
φ scans and ω scans with κ offsets | θmax = 26.3°, θmin = 4.1° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→22 |
Tmin = 0.957, Tmax = 0.966 | k = 0→16 |
40273 measured reflections | l = −25→24 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0642P)2 + 1.8417P] where P = (Fo2 + 2Fc2)/3 |
9421 reflections | (Δ/σ)max = 0.016 |
626 parameters | Δρmax = 0.40 e Å−3 |
40 restraints | Δρmin = −0.56 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes(x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151) * 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21 Rms deviation of fitted atoms = 0.0000 16.0347(0.0073) x - 4.2793(0.0107) y - 12.0383(0.0147) z = 7.5514(0.0081) Angle to previous plane(with approximate e.s.d.) = 77.6 (1) * -0.0110(0.0015) C11 * 0.0056(0.0015) C12 * 0.0073(0.0015) C13 * -0.0149(0.0015) C14 * 0.0097(0.0015) C15 * 0.0033(0.0015) C16 - 0.0447(0.0029) S1 - 0.0422(0.0030) O14 Rms deviation of fitted atoms = 0.0094 4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151) Angle to previous plane(with approximate e.s.d.) = 77.6 (1) * 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21 Rms deviation of fitted atoms = 0.0000 5.3838(0.0152) x + 5.7878(0.0113) y + 14.6111(0.0131) z = 10.1268(0.0120) Angle to previous plane(with approximate e.s.d.) = 70.5 (1) * -0.0027(0.0015) C21 * -0.0024(0.0015) C22 * 0.0071(0.0016) C23 * -0.0067(0.0016) C24 * 0.0018(0.0017) C25 * 0.0028(0.0016) C26 - 0.0890(0.0029) S1 - 0.0713(0.0031) O24 Rms deviation of fitted atoms = 0.0045 4.1891(0.0200) x - 9.1458(0.0125) y + 11.7454(0.0250) z = 1.2187(0.0151) Angle to previous plane(with approximate e.s.d.) = 70.5 (1) * 0.0000(0.0000) S1 * 0.0000(0.0000) C11 * 0.0000(0.0000) C21 Rms deviation of fitted atoms = 0.0000 15.7188(0.0137) x + 5.9495(0.0144) y - 1.9126(0.0299) z = 14.4307(0.0023) Angle to previous plane(with approximate e.s.d.) = 89.2 (1) * 0.0000(0.0000) S1 * 0.0000(0.0000) O11 * 0.0000(0.0000) O12 Rms deviation of fitted atoms = 0.0000 4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038) Angle to previous plane(with approximate e.s.d.) = 50.7 (1) * 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41 Rms deviation of fitted atoms = 0.0000 15.6735(0.0081) x + 5.3770(0.0107) y - 11.0482(0.0159) z = 2.0879(0.0031) Angle to previous plane(with approximate e.s.d.) = 75.4 (1) * -0.0124(0.0016) C31 * 0.0054(0.0016) C32 * 0.0079(0.0016) C33 * -0.0141(0.0016) C34 * 0.0070(0.0015) C35 * 0.0062(0.0015) C36 - 0.0951(0.0030) S2 - 0.0651(0.0032) O34 Rms deviation of fitted atoms = 0.0094 4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038) Angle to previous plane(with approximate e.s.d.) = 75.4 (1) * 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41 Rms deviation of fitted atoms = 0.0000 4.4832(0.0159) x - 7.2906(0.0101) y + 13.8941(0.0140) z = 3.5506(0.0054) Angle to previous plane(with approximate e.s.d.) = 71.2 (1) * 0.0052(0.0016) C41 * 0.0018(0.0016) C42 * -0.0069(0.0016) C43 * 0.0049(0.0015) C44 * 0.0021(0.0016) C45 * -0.0072(0.0016) C46 0.0350(0.0031) S2 - 0.0166(0.0030) O44 Rms deviation of fitted atoms = 0.0051 4.4528(0.0219) x + 7.9551(0.0151) y + 13.1715(0.0255) z = 3.6478(0.0038) Angle to previous plane(with approximate e.s.d.) = 71.2 (1) * 0.0000(0.0000) S2 * 0.0000(0.0000) C31 * 0.0000(0.0000) C41 Rms deviation of fitted atoms = 0.0000 15.7817(0.0144) x - 6.2114(0.0170) y - 3.5645(0.0290) z = 3.2409(0.0037) Angle to previous plane(with approximate e.s.d.) = 89.5 (1) * 0.0000(0.0000) S2 * 0.0000(0.0000) O21 * 0.0000(0.0000) O22 Rms deviation of fitted atoms = 0.0000 6.0417(0.0198) x + 7.0687(0.0115) y + 12.9412(0.0179) z = 1.0607(0.0037) Angle to previous plane(with approximate e.s.d.) = 83.2 (1) * 0.0020(0.0017) C51 * -0.0066(0.0018) C52 * 0.0027(0.0018) C53 * 0.0057(0.0017) C54 * -0.0104(0.0018) C55 * 0.0065(0.0018) C56 0.1026(0.0040) C57 0.0055(0.0042) C512_$1 [$1 is at -x, -y, -z] Rms deviation of fitted atoms = 0.0063 3.7650(0.2664) x + 8.8609(0.0647) y + 12.4642(0.2241) z = 1.4867(0.0516) Angle to previous plane(with approximate e.s.d.) = 11 (1) * 0.0000(0.0002) C71 [Atoms C71—C77, C712_$1 were constrained to be 'flat'] * 0.0000(0.0001) C72 * 0.0000(0.0003) C73 * 0.0000(0.0004) C74 * 0.0000(0.0004) C75 * 0.0000(0.0004) C76 0.0000(0.0009) C77 0.0000(0.0008) C712_$1 [$1 is at -x, -y, -z] Rms deviation of fitted atoms = 0.0000 - 4.1804(0.0171) x + 9.0707(0.0088) y - 11.8660(0.0166) z = 3.8371(0.0127) Angle to previous plane(with approximate e.s.d.) = 86.4 (5) * -0.0148(0.0017) C61 * -0.0008(0.0018) C62 * 0.0147(0.0018) C63 * -0.0128(0.0016) C64 * -0.0029(0.0016) C65 * 0.0167(0.0016) C66 - 0.0108(0.0036) C67 - 0.1343(0.0040) C612_$2 [$2 is at 1 - x, 1 - y, -z] Rms deviation of fitted atoms = 0.0122 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.75903 (3) | 0.48883 (4) | 0.21368 (3) | 0.02350 (14) | |
O11 | 0.78096 (9) | 0.45337 (11) | 0.28355 (8) | 0.0277 (4) | |
O12 | 0.72018 (9) | 0.58632 (11) | 0.19760 (8) | 0.0296 (4) | |
O14 | 0.54836 (9) | 0.18282 (11) | 0.04164 (8) | 0.0273 (4) | |
O24 | 1.02947 (9) | 0.49234 (11) | 0.11385 (9) | 0.0330 (4) | |
C11 | 0.69785 (12) | 0.39527 (15) | 0.16265 (11) | 0.0229 (5) | |
C12 | 0.69281 (13) | 0.29866 (16) | 0.18889 (11) | 0.0244 (5) | |
C13 | 0.64358 (13) | 0.22581 (16) | 0.14907 (11) | 0.0252 (5) | |
C14 | 0.59840 (12) | 0.25016 (16) | 0.08208 (11) | 0.0231 (5) | |
C15 | 0.60543 (13) | 0.34645 (16) | 0.05519 (11) | 0.0253 (5) | |
C16 | 0.65429 (13) | 0.41866 (16) | 0.09512 (11) | 0.0244 (5) | |
C21 | 0.84200 (12) | 0.49302 (15) | 0.18736 (11) | 0.0225 (5) | |
C22 | 0.89350 (13) | 0.41076 (15) | 0.20098 (11) | 0.0241 (5) | |
C23 | 0.95697 (13) | 0.41220 (16) | 0.17768 (11) | 0.0262 (5) | |
C24 | 0.97091 (13) | 0.49436 (16) | 0.13905 (12) | 0.0269 (5) | |
C25 | 0.91813 (14) | 0.57735 (17) | 0.12621 (13) | 0.0310 (5) | |
C26 | 0.85486 (14) | 0.57631 (16) | 0.15000 (12) | 0.0298 (5) | |
S2 | 0.25208 (3) | 0.01329 (4) | 0.18370 (3) | 0.03033 (16) | |
O21 | 0.20992 (10) | −0.07990 (12) | 0.15944 (10) | 0.0423 (5) | |
O22 | 0.27674 (10) | 0.03464 (12) | 0.25570 (9) | 0.0361 (4) | |
O34 | 0.04209 (9) | 0.34211 (12) | 0.04311 (8) | 0.0329 (4) | |
O44 | 0.52878 (9) | 0.01555 (11) | 0.09189 (8) | 0.0286 (4) | |
C31 | 0.19312 (12) | 0.11512 (16) | 0.14213 (12) | 0.0263 (5) | |
C32 | 0.14907 (14) | 0.10532 (17) | 0.07326 (13) | 0.0315 (5) | |
C33 | 0.09977 (14) | 0.18277 (18) | 0.04079 (12) | 0.0314 (5) | |
C34 | 0.09371 (13) | 0.27026 (17) | 0.07676 (12) | 0.0262 (5) | |
C35 | 0.13909 (13) | 0.28190 (16) | 0.14490 (11) | 0.0265 (5) | |
C36 | 0.18863 (13) | 0.20409 (16) | 0.17738 (12) | 0.0260 (5) | |
C41 | 0.33383 (13) | 0.01407 (16) | 0.15559 (12) | 0.0271 (5) | |
C42 | 0.34412 (13) | −0.06182 (16) | 0.11220 (12) | 0.0282 (5) | |
C43 | 0.40931 (13) | −0.06129 (16) | 0.09082 (12) | 0.0277 (5) | |
C44 | 0.46686 (13) | 0.01470 (15) | 0.11297 (11) | 0.0243 (5) | |
C45 | 0.45501 (13) | 0.09150 (17) | 0.15689 (12) | 0.0278 (5) | |
C46 | 0.38945 (13) | 0.09123 (17) | 0.17724 (12) | 0.0298 (5) | |
N51 | 0.05031 (12) | −0.18651 (17) | 0.13235 (10) | 0.0278 (5) | 0.920 (3) |
N52 | 0.10277 (14) | −0.36563 (19) | 0.06923 (12) | 0.0245 (6) | 0.920 (3) |
N53 | 0.14937 (13) | −0.27976 (16) | −0.03495 (12) | 0.0295 (6) | 0.920 (3) |
C51 | −0.14282 (15) | 0.11121 (18) | 0.08805 (13) | 0.0258 (6) | 0.920 (3) |
C52 | −0.07745 (16) | 0.08864 (19) | 0.06919 (13) | 0.0302 (6) | 0.920 (3) |
C53 | −0.03198 (15) | 0.00389 (18) | 0.09498 (13) | 0.0292 (6) | 0.920 (3) |
C54 | −0.05066 (15) | −0.06228 (17) | 0.14007 (13) | 0.0265 (6) | 0.920 (3) |
C55 | −0.11731 (15) | −0.04066 (19) | 0.15813 (14) | 0.0299 (6) | 0.920 (3) |
C56 | −0.16200 (16) | 0.0453 (2) | 0.13334 (15) | 0.0294 (6) | 0.920 (3) |
C57 | 0.00087 (15) | −0.15156 (18) | 0.17227 (13) | 0.0294 (6) | 0.920 (3) |
C58 | 0.10597 (15) | −0.26329 (17) | 0.16995 (12) | 0.0273 (6) | 0.920 (3) |
C59 | 0.15338 (16) | −0.30464 (18) | 0.12682 (13) | 0.0277 (6) | 0.920 (3) |
C510 | 0.14472 (16) | −0.4291 (2) | 0.03200 (14) | 0.0306 (7) | 0.920 (3) |
C511 | 0.19490 (16) | −0.3649 (2) | 0.00105 (15) | 0.0337 (7) | 0.920 (3) |
C512 | 0.19244 (16) | −0.20398 (19) | −0.06081 (14) | 0.0299 (6) | 0.920 (3) |
N61 | 0.43281 (11) | 0.31397 (13) | −0.20955 (9) | 0.0262 (4) | |
N62 | 0.40386 (10) | 0.15458 (13) | −0.06891 (9) | 0.0231 (4) | |
N63 | 0.34363 (11) | 0.25746 (14) | 0.02518 (10) | 0.0299 (4) | |
C61 | 0.64295 (14) | 0.58929 (17) | −0.09817 (12) | 0.0294 (5) | |
C62 | 0.57006 (14) | 0.56489 (18) | −0.09232 (13) | 0.0351 (6) | |
C63 | 0.52341 (14) | 0.49053 (17) | −0.13403 (13) | 0.0337 (6) | |
C64 | 0.54806 (13) | 0.43687 (16) | −0.18142 (11) | 0.0259 (5) | |
C65 | 0.61988 (14) | 0.46260 (17) | −0.18789 (12) | 0.0288 (5) | |
C66 | 0.66614 (14) | 0.53851 (17) | −0.14781 (12) | 0.0287 (5) | |
C67 | 0.49920 (13) | 0.35449 (16) | −0.22735 (12) | 0.0266 (5) | |
C68 | 0.45527 (13) | 0.25561 (17) | −0.14638 (12) | 0.0286 (5) | |
C69 | 0.38395 (14) | 0.22882 (16) | −0.12611 (11) | 0.0281 (5) | |
C610 | 0.33612 (13) | 0.11221 (16) | −0.05163 (12) | 0.0275 (5) | |
C611 | 0.29077 (14) | 0.19370 (17) | −0.02772 (12) | 0.0302 (5) | |
C612 | 0.30250 (15) | 0.33621 (18) | 0.05036 (13) | 0.0352 (6) | |
N71 | 0.0735 (8) | −0.1903 (13) | 0.2048 (8) | 0.031 (3)* | 0.080 (3) |
N72 | 0.0948 (13) | −0.353 (2) | 0.0625 (13) | 0.031 (3)* | 0.080 (3) |
N73 | 0.1472 (11) | −0.2484 (18) | −0.0272 (16) | 0.031 (3)* | 0.080 (3) |
C71 | −0.1343 (8) | 0.0863 (10) | 0.0985 (10) | 0.031 (3)* | 0.080 (3) |
C72 | −0.0614 (9) | 0.0638 (13) | 0.0925 (10) | 0.031 (3)* | 0.080 (3) |
C73 | −0.0156 (8) | −0.0122 (13) | 0.1327 (9) | 0.031 (3)* | 0.080 (3) |
C74 | −0.0417 (8) | −0.0666 (9) | 0.1792 (7) | 0.031 (3)* | 0.080 (3) |
C75 | −0.1147 (10) | −0.0440 (14) | 0.1852 (11) | 0.031 (3)* | 0.080 (3) |
C76 | −0.1606 (10) | 0.0319 (15) | 0.1451 (12) | 0.031 (3)* | 0.080 (3) |
C77 | 0.0077 (10) | −0.1498 (11) | 0.2234 (8) | 0.031 (3)* | 0.080 (3) |
C78 | 0.0486 (10) | −0.247 (2) | 0.1407 (12) | 0.031 (3)* | 0.080 (3) |
C79 | 0.1191 (11) | −0.282 (2) | 0.1217 (14) | 0.031 (3)* | 0.080 (3) |
C710 | 0.1595 (16) | −0.4008 (12) | 0.0438 (13) | 0.031 (3)* | 0.080 (3) |
C711 | 0.2013 (12) | −0.3259 (18) | 0.0112 (16) | 0.031 (3)* | 0.080 (3) |
C712 | 0.1850 (9) | −0.1689 (14) | −0.0551 (13) | 0.031 (3)* | 0.080 (3) |
H14 | 0.5501 | 0.1277 | 0.0629 | 0.041* | |
H12 | 0.7233 | 0.2825 | 0.2344 | 0.029* | |
H13 | 0.6405 | 0.1598 | 0.1671 | 0.030* | |
H15 | 0.5764 | 0.3620 | 0.0092 | 0.030* | |
H16 | 0.6584 | 0.4842 | 0.0769 | 0.029* | |
H22 | 0.8847 | 0.3539 | 0.2263 | 0.029* | |
H23 | 0.9923 | 0.3564 | 0.1879 | 0.031* | |
H25 | 0.9265 | 0.6344 | 0.1009 | 0.037* | |
H26 | 0.8198 | 0.6325 | 0.1410 | 0.036* | |
H34 | 0.0426 | 0.3910 | 0.0696 | 0.049* | |
H32 | 0.1531 | 0.0452 | 0.0488 | 0.038* | |
H33 | 0.0700 | 0.1763 | −0.0061 | 0.038* | |
H35 | 0.1360 | 0.3429 | 0.1689 | 0.032* | |
H36 | 0.2196 | 0.2115 | 0.2239 | 0.031* | |
H42 | 0.3062 | −0.1142 | 0.0972 | 0.034* | |
H43 | 0.4155 | −0.1131 | 0.0606 | 0.033* | |
H45 | 0.4928 | 0.1439 | 0.1725 | 0.033* | |
H46 | 0.3819 | 0.1439 | 0.2062 | 0.036* | |
H51A | 0.0769 | −0.1319 | 0.1225 | 0.033* | 0.920 (3) |
H52A | 0.0699 | −0.3219 | 0.0385 | 0.029* | 0.920 (3) |
H52B | 0.0723 | −0.4079 | 0.0860 | 0.029* | 0.920 (3) |
H53A | 0.1095 | −0.3047 | −0.0713 | 0.035* | 0.920 (3) |
H52 | −0.0635 | 0.1322 | 0.0380 | 0.036* | 0.920 (3) |
H53 | 0.0129 | −0.0092 | 0.0815 | 0.035* | 0.920 (3) |
H55 | −0.1324 | −0.0856 | 0.1880 | 0.036* | 0.920 (3) |
H56 | −0.2063 | 0.0594 | 0.1475 | 0.035* | 0.920 (3) |
H57A | 0.0345 | −0.1316 | 0.2185 | 0.035* | 0.920 (3) |
H57B | −0.0325 | −0.2089 | 0.1776 | 0.035* | 0.920 (3) |
H58A | 0.0775 | −0.3199 | 0.1833 | 0.033* | 0.920 (3) |
H58B | 0.1414 | −0.2325 | 0.2122 | 0.033* | 0.920 (3) |
H59A | 0.1768 | −0.2474 | 0.1087 | 0.033* | 0.920 (3) |
H59B | 0.1962 | −0.3479 | 0.1554 | 0.033* | 0.920 (3) |
H51C | 0.1062 | −0.4674 | −0.0048 | 0.037* | 0.920 (3) |
H51D | 0.1781 | −0.4792 | 0.0641 | 0.037* | 0.920 (3) |
H51E | 0.2412 | −0.3397 | 0.0376 | 0.040* | 0.920 (3) |
H51F | 0.2131 | −0.4067 | −0.0310 | 0.040* | 0.920 (3) |
H51G | 0.2094 | −0.2346 | −0.0978 | 0.036* | 0.920 (3) |
H51H | 0.2396 | −0.1831 | −0.0235 | 0.036* | 0.920 (3) |
H61A | 0.4015 | 0.3673 | −0.2054 | 0.031* | |
H62A | 0.4365 | 0.1859 | −0.0306 | 0.028* | |
H62B | 0.4310 | 0.1014 | −0.0799 | 0.028* | |
H63A | 0.3709 | 0.2168 | 0.0612 | 0.036* | |
H62 | 0.5520 | 0.5994 | −0.0595 | 0.042* | |
H63 | 0.4735 | 0.4763 | −0.1298 | 0.040* | |
H65 | 0.6380 | 0.4276 | −0.2204 | 0.035* | |
H66 | 0.7143 | 0.5559 | −0.1545 | 0.034* | |
H67A | 0.4795 | 0.3823 | −0.2744 | 0.032* | |
H67B | 0.5341 | 0.2968 | −0.2285 | 0.032* | |
H68A | 0.4919 | 0.2961 | −0.1095 | 0.034* | |
H68B | 0.4822 | 0.1923 | −0.1527 | 0.034* | |
H69A | 0.3624 | 0.2915 | −0.1121 | 0.034* | |
H69B | 0.3435 | 0.1993 | −0.1659 | 0.034* | |
H61B | 0.3548 | 0.0604 | −0.0151 | 0.033* | |
H61C | 0.3008 | 0.0777 | −0.0924 | 0.033* | |
H61D | 0.2620 | 0.2368 | −0.0670 | 0.036* | |
H61E | 0.2522 | 0.1609 | −0.0092 | 0.036* | |
H61F | 0.2694 | 0.3033 | 0.0747 | 0.042* | |
H61G | 0.2678 | 0.3741 | 0.0109 | 0.042* | |
H71A | 0.1051 | −0.1373 | 0.2008 | 0.037* | 0.080 (3) |
H72B | 0.0646 | −0.4034 | 0.0723 | 0.037* | 0.080 (3) |
H72A | 0.0639 | −0.3174 | 0.0252 | 0.037* | 0.080 (3) |
H73A | 0.1096 | −0.2794 | −0.0626 | 0.037* | 0.080 (3) |
H72 | −0.0429 | 0.1004 | 0.0608 | 0.037* | 0.080 (3) |
H73 | 0.0341 | −0.0271 | 0.1283 | 0.037* | 0.080 (3) |
H75 | −0.1332 | −0.0806 | 0.2168 | 0.037* | 0.080 (3) |
H76 | −0.2103 | 0.0469 | 0.1495 | 0.037* | 0.080 (3) |
H77A | 0.0281 | −0.1231 | 0.2707 | 0.037* | 0.080 (3) |
H77B | −0.0272 | −0.2075 | 0.2244 | 0.037* | 0.080 (3) |
H78A | 0.0152 | −0.2031 | 0.1039 | 0.037* | 0.080 (3) |
H78B | 0.0175 | −0.3071 | 0.1456 | 0.037* | 0.080 (3) |
H79A | 0.1457 | −0.2219 | 0.1098 | 0.037* | 0.080 (3) |
H79B | 0.1564 | −0.3166 | 0.1612 | 0.037* | 0.080 (3) |
H71C | 0.1386 | −0.4575 | 0.0115 | 0.037* | 0.080 (3) |
H71D | 0.1974 | −0.4299 | 0.0854 | 0.037* | 0.080 (3) |
H71E | 0.2443 | −0.2928 | 0.0473 | 0.037* | 0.080 (3) |
H71F | 0.2242 | −0.3629 | −0.0199 | 0.037* | 0.080 (3) |
H71G | 0.2136 | −0.2025 | −0.0831 | 0.037* | 0.080 (3) |
H71H | 0.2244 | −0.1354 | −0.0162 | 0.037* | 0.080 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0226 (3) | 0.0227 (3) | 0.0263 (3) | 0.0020 (2) | 0.0092 (2) | −0.0022 (2) |
O11 | 0.0291 (9) | 0.0318 (8) | 0.0231 (8) | 0.0004 (7) | 0.0094 (7) | −0.0037 (6) |
O12 | 0.0275 (9) | 0.0236 (8) | 0.0388 (10) | 0.0052 (6) | 0.0118 (7) | −0.0021 (7) |
O14 | 0.0264 (9) | 0.0291 (8) | 0.0245 (8) | −0.0029 (7) | 0.0055 (7) | −0.0015 (6) |
O24 | 0.0290 (9) | 0.0293 (8) | 0.0474 (11) | −0.0010 (7) | 0.0216 (8) | 0.0048 (7) |
C11 | 0.0198 (11) | 0.0243 (10) | 0.0260 (12) | 0.0008 (9) | 0.0094 (9) | −0.0015 (8) |
C12 | 0.0217 (11) | 0.0297 (11) | 0.0215 (11) | 0.0024 (9) | 0.0063 (9) | 0.0027 (9) |
C13 | 0.0240 (12) | 0.0263 (11) | 0.0267 (12) | 0.0005 (9) | 0.0099 (10) | 0.0027 (9) |
C14 | 0.0186 (11) | 0.0293 (11) | 0.0239 (12) | 0.0024 (9) | 0.0100 (9) | −0.0032 (9) |
C15 | 0.0231 (12) | 0.0300 (11) | 0.0223 (11) | 0.0043 (9) | 0.0064 (9) | 0.0031 (9) |
C16 | 0.0243 (12) | 0.0245 (11) | 0.0260 (12) | 0.0028 (9) | 0.0103 (10) | 0.0023 (9) |
C21 | 0.0204 (11) | 0.0230 (10) | 0.0243 (11) | 0.0000 (8) | 0.0071 (9) | −0.0023 (8) |
C22 | 0.0244 (12) | 0.0216 (10) | 0.0264 (12) | −0.0002 (9) | 0.0080 (10) | 0.0022 (9) |
C23 | 0.0239 (12) | 0.0247 (11) | 0.0296 (13) | 0.0044 (9) | 0.0077 (10) | 0.0026 (9) |
C24 | 0.0234 (12) | 0.0244 (11) | 0.0334 (13) | −0.0033 (9) | 0.0095 (10) | 0.0000 (9) |
C25 | 0.0316 (13) | 0.0229 (11) | 0.0422 (14) | 0.0006 (9) | 0.0168 (11) | 0.0059 (10) |
C26 | 0.0295 (13) | 0.0211 (10) | 0.0382 (14) | 0.0036 (9) | 0.0096 (11) | 0.0029 (9) |
S2 | 0.0269 (3) | 0.0256 (3) | 0.0439 (4) | −0.0009 (2) | 0.0189 (3) | 0.0000 (2) |
O21 | 0.0355 (10) | 0.0259 (8) | 0.0725 (14) | −0.0058 (7) | 0.0271 (10) | −0.0043 (8) |
O22 | 0.0330 (10) | 0.0359 (9) | 0.0460 (11) | 0.0073 (7) | 0.0219 (8) | 0.0104 (8) |
O34 | 0.0284 (9) | 0.0381 (9) | 0.0310 (9) | 0.0040 (7) | 0.0076 (7) | 0.0005 (7) |
O44 | 0.0254 (9) | 0.0272 (8) | 0.0364 (9) | 0.0022 (6) | 0.0143 (7) | −0.0023 (7) |
C31 | 0.0174 (11) | 0.0281 (11) | 0.0358 (13) | −0.0024 (9) | 0.0118 (10) | −0.0027 (9) |
C32 | 0.0290 (13) | 0.0313 (12) | 0.0380 (14) | −0.0051 (10) | 0.0159 (11) | −0.0117 (10) |
C33 | 0.0245 (12) | 0.0425 (14) | 0.0289 (13) | −0.0053 (10) | 0.0107 (10) | −0.0076 (10) |
C34 | 0.0187 (11) | 0.0328 (12) | 0.0301 (13) | −0.0017 (9) | 0.0119 (10) | 0.0003 (9) |
C35 | 0.0252 (12) | 0.0273 (11) | 0.0300 (13) | −0.0010 (9) | 0.0131 (10) | −0.0052 (9) |
C36 | 0.0207 (12) | 0.0321 (12) | 0.0277 (12) | −0.0019 (9) | 0.0111 (10) | −0.0035 (9) |
C41 | 0.0238 (12) | 0.0248 (11) | 0.0364 (13) | 0.0020 (9) | 0.0147 (10) | 0.0006 (9) |
C42 | 0.0254 (12) | 0.0230 (11) | 0.0355 (14) | −0.0022 (9) | 0.0087 (10) | −0.0015 (9) |
C43 | 0.0308 (13) | 0.0217 (11) | 0.0310 (13) | 0.0044 (9) | 0.0102 (10) | −0.0037 (9) |
C44 | 0.0231 (12) | 0.0249 (11) | 0.0256 (12) | 0.0032 (9) | 0.0087 (9) | 0.0028 (9) |
C45 | 0.0239 (12) | 0.0270 (11) | 0.0330 (13) | −0.0035 (9) | 0.0095 (10) | −0.0042 (9) |
C46 | 0.0298 (13) | 0.0278 (11) | 0.0339 (13) | −0.0025 (10) | 0.0132 (11) | −0.0075 (9) |
N51 | 0.0263 (12) | 0.0309 (12) | 0.0285 (12) | −0.0023 (9) | 0.0119 (9) | 0.0019 (9) |
N52 | 0.0222 (11) | 0.0264 (12) | 0.0255 (12) | −0.0015 (9) | 0.0081 (9) | 0.0048 (9) |
N53 | 0.0313 (12) | 0.0313 (12) | 0.0272 (13) | −0.0051 (10) | 0.0110 (10) | −0.0002 (10) |
C51 | 0.0289 (14) | 0.0247 (12) | 0.0257 (14) | −0.0057 (10) | 0.0110 (11) | −0.0052 (10) |
C52 | 0.0376 (16) | 0.0296 (13) | 0.0294 (15) | −0.0034 (11) | 0.0193 (13) | −0.0002 (11) |
C53 | 0.0293 (14) | 0.0328 (13) | 0.0315 (15) | −0.0029 (11) | 0.0181 (12) | −0.0018 (11) |
C54 | 0.0325 (14) | 0.0244 (12) | 0.0246 (14) | −0.0068 (10) | 0.0121 (11) | −0.0069 (10) |
C55 | 0.0332 (15) | 0.0310 (13) | 0.0304 (15) | −0.0089 (11) | 0.0170 (13) | −0.0012 (11) |
C56 | 0.0280 (14) | 0.0330 (14) | 0.0324 (16) | −0.0072 (11) | 0.0169 (12) | −0.0027 (11) |
C57 | 0.0356 (15) | 0.0269 (12) | 0.0292 (14) | −0.0051 (11) | 0.0153 (12) | −0.0018 (10) |
C58 | 0.0292 (14) | 0.0279 (12) | 0.0238 (13) | −0.0035 (10) | 0.0067 (11) | 0.0027 (10) |
C59 | 0.0258 (14) | 0.0276 (13) | 0.0270 (14) | −0.0037 (10) | 0.0045 (11) | 0.0005 (10) |
C510 | 0.0325 (16) | 0.0275 (13) | 0.0361 (16) | −0.0023 (11) | 0.0167 (13) | −0.0015 (11) |
C511 | 0.0354 (16) | 0.0295 (13) | 0.0422 (17) | 0.0017 (12) | 0.0211 (13) | −0.0009 (12) |
C512 | 0.0354 (15) | 0.0311 (13) | 0.0296 (14) | −0.0032 (12) | 0.0194 (12) | −0.0023 (11) |
N61 | 0.0282 (11) | 0.0239 (9) | 0.0279 (10) | 0.0007 (8) | 0.0106 (8) | 0.0008 (7) |
N62 | 0.0242 (10) | 0.0231 (9) | 0.0221 (10) | 0.0023 (7) | 0.0075 (8) | −0.0010 (7) |
N63 | 0.0315 (11) | 0.0321 (10) | 0.0262 (10) | 0.0027 (8) | 0.0092 (9) | −0.0060 (8) |
C61 | 0.0276 (13) | 0.0302 (12) | 0.0333 (13) | 0.0016 (10) | 0.0140 (11) | −0.0020 (10) |
C62 | 0.0334 (14) | 0.0360 (13) | 0.0427 (15) | −0.0001 (11) | 0.0216 (12) | −0.0118 (11) |
C63 | 0.0299 (13) | 0.0336 (13) | 0.0442 (15) | −0.0052 (10) | 0.0211 (12) | −0.0074 (11) |
C64 | 0.0292 (12) | 0.0224 (10) | 0.0276 (12) | 0.0033 (9) | 0.0109 (10) | 0.0029 (9) |
C65 | 0.0296 (13) | 0.0300 (12) | 0.0306 (13) | 0.0033 (10) | 0.0150 (11) | −0.0026 (9) |
C66 | 0.0245 (12) | 0.0341 (12) | 0.0306 (13) | −0.0003 (10) | 0.0133 (10) | −0.0009 (10) |
C67 | 0.0295 (12) | 0.0252 (11) | 0.0274 (12) | 0.0024 (9) | 0.0120 (10) | −0.0009 (9) |
C68 | 0.0281 (13) | 0.0275 (11) | 0.0312 (13) | −0.0022 (9) | 0.0105 (10) | 0.0007 (9) |
C69 | 0.0313 (13) | 0.0270 (11) | 0.0258 (12) | 0.0025 (10) | 0.0084 (10) | 0.0026 (9) |
C610 | 0.0302 (13) | 0.0286 (11) | 0.0263 (12) | −0.0049 (10) | 0.0127 (10) | 0.0000 (9) |
C611 | 0.0298 (13) | 0.0352 (12) | 0.0281 (13) | −0.0045 (10) | 0.0129 (11) | −0.0057 (10) |
C612 | 0.0303 (13) | 0.0393 (13) | 0.0403 (15) | −0.0016 (11) | 0.0174 (11) | −0.0099 (11) |
S1—O11 | 1.443 (2) | C51—C52 | 1.385 (4) |
S1—O12 | 1.445 (2) | C51—C56 | 1.391 (3) |
S1—C21 | 1.746 (2) | C52—C53 | 1.384 (3) |
S1—C11 | 1.761 (2) | C53—C54 | 1.386 (3) |
O14—C14 | 1.348 (3) | C54—C55 | 1.395 (4) |
O24—C24 | 1.315 (3) | C54—C57 | 1.512 (3) |
C11—C12 | 1.391 (3) | C55—C56 | 1.387 (4) |
C11—C16 | 1.399 (3) | C58—C59 | 1.513 (4) |
C12—C13 | 1.384 (3) | C510—C511 | 1.515 (4) |
C13—C14 | 1.401 (3) | N61—C68 | 1.452 (3) |
C14—C15 | 1.400 (3) | N61—C67 | 1.459 (3) |
C15—C16 | 1.376 (3) | N62—C69 | 1.482 (3) |
C21—C22 | 1.394 (3) | N62—C610 | 1.484 (3) |
C21—C26 | 1.396 (3) | N63—C612 | 1.458 (3) |
C22—C23 | 1.374 (3) | N63—C611 | 1.464 (3) |
C23—C24 | 1.407 (3) | C61—C66 | 1.389 (3) |
C24—C25 | 1.415 (3) | C61—C62 | 1.395 (3) |
C25—C26 | 1.377 (3) | C61—C612ii | 1.511 (3) |
S2—O22 | 1.434 (2) | C62—C63 | 1.394 (3) |
S2—O21 | 1.443 (2) | C63—C64 | 1.384 (3) |
S2—C41 | 1.746 (2) | C64—C65 | 1.386 (3) |
S2—C31 | 1.754 (2) | C64—C67 | 1.521 (3) |
O34—C34 | 1.353 (3) | C65—C66 | 1.391 (3) |
O44—C44 | 1.320 (3) | C68—C69 | 1.514 (3) |
C31—C36 | 1.389 (3) | C610—C611 | 1.518 (3) |
C31—C32 | 1.397 (3) | C612—C61ii | 1.511 (3) |
C32—C33 | 1.377 (3) | N71—C77 | 1.457 (4) |
C33—C34 | 1.387 (3) | N71—C78 | 1.458 (4) |
C34—C35 | 1.393 (3) | N72—C710 | 1.482 (4) |
C35—C36 | 1.383 (3) | N72—C79 | 1.484 (4) |
C41—C42 | 1.387 (3) | N73—C712 | 1.457 (4) |
C41—C46 | 1.396 (3) | N73—C711 | 1.458 (4) |
C42—C43 | 1.379 (3) | C71—C712i | 1.517 (12) |
C43—C44 | 1.408 (3) | C71—C76 | 1.391 (4) |
C44—C45 | 1.413 (3) | C71—C72 | 1.392 (4) |
C45—C46 | 1.373 (3) | C72—C73 | 1.390 (4) |
N51—C58 | 1.461 (3) | C73—C74 | 1.390 (4) |
N51—C57 | 1.463 (3) | C74—C75 | 1.392 (4) |
N52—C59 | 1.483 (3) | C74—C77 | 1.517 (4) |
N52—C510 | 1.488 (3) | C75—C76 | 1.389 (4) |
N53—C511 | 1.445 (3) | C78—C79 | 1.514 (4) |
N53—C512 | 1.461 (3) | C710—C711 | 1.516 (4) |
C51—C512i | 1.510 (3) | ||
O11—S1—O12 | 118.4 (1) | C59—N52—C510 | 115.3 (2) |
O11—S1—C21 | 108.96 (10) | C511—N53—C512 | 115.5 (2) |
O12—S1—C21 | 107.65 (10) | C52—C51—C56 | 117.9 (2) |
O11—S1—C11 | 107.14 (10) | C53—C52—C51 | 121.3 (2) |
O12—S1—C11 | 108.09 (10) | C52—C53—C54 | 121.3 (2) |
C21—S1—C11 | 106.0 (1) | C53—C54—C55 | 117.5 (2) |
C12—C11—C16 | 120.0 (2) | C53—C54—C57 | 122.1 (2) |
C12—C11—S1 | 120.53 (17) | C55—C54—C57 | 120.3 (2) |
C16—C11—S1 | 119.47 (16) | C56—C55—C54 | 121.2 (2) |
C13—C12—C11 | 120.4 (2) | C55—C56—C51 | 120.8 (2) |
C12—C13—C14 | 119.5 (2) | N51—C57—C54 | 113.3 (2) |
O14—C14—C15 | 118.2 (2) | N51—C58—C59 | 111.0 (2) |
O14—C14—C13 | 122.0 (2) | N52—C59—C58 | 110.0 (2) |
C15—C14—C13 | 119.8 (2) | N52—C510—C511 | 112.0 (2) |
C16—C15—C14 | 120.3 (2) | N53—C511—C510 | 109.0 (2) |
C15—C16—C11 | 119.8 (2) | N53—C512—C51i | 111.19 (19) |
C22—C21—C26 | 120.0 (2) | C68—N61—C67 | 113.29 (18) |
C22—C21—S1 | 119.76 (16) | C69—N62—C610 | 115.02 (17) |
C26—C21—S1 | 120.15 (16) | C612—N63—C611 | 112.47 (18) |
C23—C22—C21 | 119.7 (2) | C66—C61—C62 | 117.6 (2) |
C22—C23—C24 | 121.6 (2) | C66—C61—C612ii | 120.2 (2) |
O24—C24—C23 | 121.0 (2) | C62—C61—C612ii | 122.1 (2) |
O24—C24—C25 | 121.3 (2) | C63—C62—C61 | 120.8 (2) |
C23—C24—C25 | 117.7 (2) | C64—C63—C62 | 121.6 (2) |
C26—C25—C24 | 120.7 (2) | C63—C64—C65 | 117.5 (2) |
C25—C26—C21 | 120.2 (2) | C63—C64—C67 | 123.1 (2) |
O22—S2—O21 | 118.8 (1) | C65—C64—C67 | 119.4 (2) |
O22—S2—C41 | 108.65 (11) | C64—C65—C66 | 121.5 (2) |
O21—S2—C41 | 107.42 (10) | C61—C66—C65 | 121.0 (2) |
O22—S2—C31 | 107.44 (10) | N61—C67—C64 | 117.69 (18) |
O21—S2—C31 | 107.56 (11) | N61—C68—C69 | 110.22 (18) |
C41—S2—C31 | 106.3 (1) | N62—C69—C68 | 110.82 (18) |
C36—C31—C32 | 119.9 (2) | N62—C610—C611 | 112.51 (17) |
C36—C31—S2 | 120.68 (18) | N63—C611—C610 | 110.51 (19) |
C32—C31—S2 | 119.37 (17) | N63—C612—C61ii | 112.8 (2) |
C33—C32—C31 | 120.0 (2) | C77—N71—C78 | 112.2 (7) |
C32—C33—C34 | 119.8 (2) | C710—N72—C79 | 115.1 (8) |
O34—C34—C33 | 117.3 (2) | C712—N73—C711 | 113.2 (7) |
O34—C34—C35 | 122.2 (2) | C76—C71—C72 | 119.3 (5) |
C33—C34—C35 | 120.5 (2) | C73—C72—C71 | 120.1 (6) |
C36—C35—C34 | 119.5 (2) | C72—C73—C74 | 120.7 (6) |
C35—C36—C31 | 120.1 (2) | C73—C74—C75 | 119.0 (5) |
C42—C41—C46 | 119.8 (2) | C73—C74—C77 | 121.3 (6) |
C42—C41—S2 | 120.42 (17) | C75—C74—C77 | 119.7 (6) |
C46—C41—S2 | 119.79 (17) | C76—C75—C74 | 120.4 (6) |
C43—C42—C41 | 120.1 (2) | C75—C76—C71 | 120.4 (6) |
C42—C43—C44 | 121.1 (2) | N71—C77—C74 | 118.6 (7) |
O44—C44—C43 | 121.0 (2) | N71—C78—C79 | 110.0 (7) |
O44—C44—C45 | 121.2 (2) | N72—C79—C78 | 110.1 (7) |
C43—C44—C45 | 117.8 (2) | N72—C710—C711 | 112.4 (8) |
C46—C45—C44 | 120.7 (2) | N73—C711—C710 | 110.5 (7) |
C45—C46—C41 | 120.5 (2) | N73—C712—C71i | 118.1 (9) |
C58—N51—C57 | 110.98 (19) | ||
O11—S1—C11—C12 | −14.0 (2) | C43—C44—C45—C46 | 0.2 (3) |
O12—S1—C11—C12 | −142.55 (18) | C44—C45—C46—C41 | 0.9 (3) |
C21—S1—C11—C12 | 102.26 (19) | C42—C41—C46—C45 | −1.2 (4) |
O11—S1—C11—C16 | 166.21 (17) | S2—C41—C46—C45 | 178.42 (18) |
O12—S1—C11—C16 | 37.6 (2) | C56—C51—C52—C53 | −0.6 (4) |
C21—S1—C11—C16 | −77.54 (19) | C51—C52—C53—C54 | 0.7 (4) |
C16—C11—C12—C13 | −1.4 (3) | C52—C53—C54—C55 | 0.4 (4) |
S1—C11—C12—C13 | 178.80 (17) | C52—C53—C54—C57 | −176.1 (2) |
C11—C12—C13—C14 | −0.3 (3) | C53—C54—C55—C56 | −1.7 (4) |
C12—C13—C14—O14 | −178.6 (2) | C57—C54—C55—C56 | 174.9 (2) |
C12—C13—C14—C15 | 2.3 (3) | C54—C55—C56—C51 | 1.8 (4) |
O14—C14—C15—C16 | 178.33 (19) | C52—C51—C56—C55 | −0.6 (4) |
C13—C14—C15—C16 | −2.5 (3) | C58—N51—C57—C54 | 172.4 (2) |
C14—C15—C16—C11 | 0.8 (3) | C53—C54—C57—N51 | −24.2 (3) |
C12—C11—C16—C15 | 1.2 (3) | C55—C54—C57—N51 | 159.4 (2) |
S1—C11—C16—C15 | −179.04 (17) | C57—N51—C58—C59 | 176.14 (19) |
O11—S1—C21—C22 | 46.2 (2) | C510—N52—C59—C58 | −167.1 (2) |
O12—S1—C21—C22 | 175.70 (17) | N51—C58—C59—N52 | −68.4 (3) |
C11—S1—C21—C22 | −68.82 (19) | C59—N52—C510—C511 | −59.7 (3) |
O11—S1—C21—C26 | −136.80 (18) | C512—N53—C511—C510 | 173.0 (2) |
O12—S1—C21—C26 | −7.3 (2) | N52—C510—C511—N53 | −47.8 (3) |
C11—S1—C21—C26 | 108.19 (19) | C511—N53—C512—C51i | −171.56 (19) |
C26—C21—C22—C23 | 0.2 (3) | C66—C61—C62—C63 | 1.4 (4) |
S1—C21—C22—C23 | 177.19 (17) | C612ii—C61—C62—C63 | −175.4 (2) |
C21—C22—C23—C24 | −1.1 (3) | C61—C62—C63—C64 | 1.4 (4) |
C22—C23—C24—O24 | −176.2 (2) | C62—C63—C64—C65 | −2.5 (4) |
C22—C23—C24—C25 | 1.5 (3) | C62—C63—C64—C67 | 179.4 (2) |
O24—C24—C25—C26 | 176.8 (2) | C63—C64—C65—C66 | 0.8 (3) |
C23—C24—C25—C26 | −1.0 (3) | C67—C64—C65—C66 | 179.0 (2) |
C24—C25—C26—C21 | 0.1 (4) | C62—C61—C66—C65 | −3.1 (3) |
C22—C21—C26—C25 | 0.3 (3) | C612ii—C61—C66—C65 | 173.8 (2) |
S1—C21—C26—C25 | −176.67 (18) | C64—C65—C66—C61 | 2.0 (4) |
O22—S2—C31—C36 | 10.8 (2) | C68—N61—C67—C64 | −67.5 (2) |
O21—S2—C31—C36 | 139.84 (18) | C63—C64—C67—N61 | −14.9 (3) |
C41—S2—C31—C36 | −105.34 (19) | C65—C64—C67—N61 | 166.99 (19) |
O22—S2—C31—C32 | −167.76 (18) | C67—N61—C68—C69 | 172.08 (17) |
O21—S2—C31—C32 | −38.8 (2) | C610—N62—C69—C68 | −171.77 (17) |
C41—S2—C31—C32 | 76.1 (2) | N61—C68—C69—N62 | 170.13 (17) |
C36—C31—C32—C33 | −1.6 (3) | C69—N62—C610—C611 | −62.4 (2) |
S2—C31—C32—C33 | 177.01 (18) | C612—N63—C611—C610 | −179.30 (19) |
C31—C32—C33—C34 | −0.3 (4) | N62—C610—C611—N63 | −49.3 (2) |
C32—C33—C34—O34 | −177.4 (2) | C611—N63—C612—C61ii | −172.6 (2) |
C32—C33—C34—C35 | 2.2 (3) | C76—C71—C72—C73 | 0.00 (3) |
O34—C34—C35—C36 | 177.5 (2) | C71—C72—C73—C74 | 0.00 (3) |
C33—C34—C35—C36 | −2.1 (3) | C72—C73—C74—C75 | 0.00 (7) |
C34—C35—C36—C31 | 0.1 (3) | C72—C73—C74—C77 | 180.00 (4) |
C32—C31—C36—C35 | 1.7 (3) | C73—C74—C75—C76 | 0.00 (9) |
S2—C31—C36—C35 | −176.90 (17) | C77—C74—C75—C76 | 180.00 (6) |
O22—S2—C41—C42 | 135.38 (19) | C74—C75—C76—C71 | 0.00 (9) |
O21—S2—C41—C42 | 5.7 (2) | C72—C71—C76—C75 | 0.00 (7) |
C31—S2—C41—C42 | −109.2 (2) | C78—N71—C77—C74 | −67 (2) |
O22—S2—C41—C46 | −44.2 (2) | C73—C74—C77—N71 | −16 (2) |
O21—S2—C41—C46 | −173.94 (19) | C75—C74—C77—N71 | 164.4 (13) |
C31—S2—C41—C46 | 71.1 (2) | C77—N71—C78—C79 | 177 (2) |
C46—C41—C42—C43 | 0.3 (3) | C710—N72—C79—C78 | −174 (3) |
S2—C41—C42—C43 | −179.29 (18) | N71—C78—C79—N72 | 171 (3) |
C41—C42—C43—C44 | 0.8 (3) | C79—N72—C710—C711 | −72 (4) |
C42—C43—C44—O44 | −179.3 (2) | C712—N73—C711—C710 | 175 (3) |
C42—C43—C44—C45 | −1.1 (3) | N72—C710—C711—N73 | −32 (4) |
O44—C44—C45—C46 | 178.5 (2) | C711—N73—C712—C71i | 178 (2) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···O44 | 0.84 | 1.68 | 2.496 (2) | 165 |
O34—H34···O24iii | 0.84 | 1.67 | 2.501 (2) | 171 |
N51—H51A···O21 | 0.92 | 2.38 | 3.092 (3) | 134 |
N52—H52A···O34i | 0.92 | 2.20 | 2.914 (3) | 134 |
N52—H52B···O24iv | 0.92 | 1.71 | 2.612 (3) | 167 |
N61—H61A···O12ii | 0.92 | 2.33 | 3.134 (3) | 145 |
N62—H62A···O14 | 0.92 | 2.10 | 2.898 (2) | 144 |
N62—H62B···O44v | 0.92 | 1.75 | 2.652 (2) | 168 |
C12—H12···O11 | 0.95 | 2.54 | 2.915 (3) | 104 |
C22—H22···N61vi | 0.95 | 2.57 | 3.428 (3) | 150 |
C26—H26···O12 | 0.95 | 2.50 | 2.895 (3) | 105 |
C36—H36···O22 | 0.95 | 2.54 | 2.908 (3) | 103 |
C42—H42···O21 | 0.95 | 2.50 | 2.889 (3) | 104 |
C43—H43···O14v | 0.95 | 2.56 | 3.443 (3) | 155 |
C59—H59B···O22vii | 0.99 | 2.32 | 3.156 (3) | 141 |
C610—H61C···O11viii | 0.99 | 2.50 | 3.334 (3) | 142 |
C69—H69B···O11viii | 0.99 | 2.37 | 3.232 (3) | 145 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x−1, y−1, z; (v) −x+1, −y, −z; (vi) x+1/2, −y+1/2, z+1/2; (vii) −x+1/2, y−1/2, −z+1/2; (viii) x−1/2, −y+1/2, z−1/2. |
C24H40N6·C12H10O2·2(C12H9O2)·2(H2O) | F(000) = 1076 |
Mr = 1005.23 | Dx = 1.295 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3442 (4) Å | Cell parameters from 4832 reflections |
b = 7.6496 (3) Å | θ = 4.2–25.6° |
c = 29.1745 (9) Å | µ = 0.09 mm−1 |
β = 110.686 (2)° | T = 100 K |
V = 2577.29 (15) Å3 | Plate, colourless |
Z = 2 | 0.25 × 0.20 × 0.04 mm |
Kappa-CCD diffractometer | 4832 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2686 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
φ scans and ω scans with κ offsets | θmax = 25.6°, θmin = 4.2° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = 0→15 |
Tmin = 0.979, Tmax = 0.997 | k = −9→0 |
19716 measured reflections | l = −35→32 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0568P)2] where P = (Fo2 + 2Fc2)/3 |
4832 reflections | (Δ/σ)max = 0.001 |
362 parameters | Δρmax = 0.16 e Å−3 |
14 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
Geometry. Mean-plane data from the final SHELXL97 refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.1270(0.0088) x + 6.7225(0.0031) y - 10.6934(0.0235) z = 3.9351(0.0129) * 0.0007(0.0014) C11 * -0.0050(0.0015) C12 * 0.0032(0.0015) C13 * 0.0028(0.0014) C14 * -0.0070(0.0014) C15 * 0.0053(0.0014) C16 0.0074(0.0026) O14 Rms deviation of fitted atoms = 0.0045 0.8345(0.0087) x + 7.1053(0.0023) y - 10.6384(0.0219) z = 3.2175(0.0105) Angle to previous plane (with approximate e.s.d.) = 21.6 (1) * 0.0181(0.0013) C21 * -0.0097(0.0013) C22 * -0.0118(0.0013) C23 * 0.0248(0.0013) C24 * -0.0163(0.0013) C25 * -0.0052(0.0013) C26 0.0851(0.0024) O24 0.3285(0.0051) O34 0.1078(0.0027) C31 - 0.2371(0.0033) C32 - 0.1467(0.0041) C33 0.2891(0.0044) C34 0.6581(0.0040) C35 0.5710(0.0033) C36 Rms deviation of fitted atoms = 0.0156 - 2.7414(0.0085) x - 5.7392(0.0037) y + 19.2852(0.0160) z = 1.5525(0.0110) Angle to previous plane (with approximate e.s.d.) = 20.2 (1) * 0.0068(0.0012) C31 * -0.0012(0.0013) C32 * -0.0065(0.0013) C33 * 0.0086(0.0012) C34 * -0.0029(0.0012) C35 * -0.0048(0.0012) C36 - 0.3132(0.0052) O24 0.0396(0.0024) O34 0.0035(0.0027) C21 0.3856(0.0033) C22 0.3068(0.0042) C23 - 0.1759(0.0044) C24 - 0.4971(0.0041) C25 - 0.4222(0.0033) C26 Rms deviation of fitted atoms = 0.0057 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O14 | 0.09460 (11) | 1.20777 (17) | 0.43595 (5) | 0.0351 (4) | |
C11 | 0.43918 (16) | 1.0304 (2) | 0.49026 (7) | 0.0299 (5) | |
C12 | 0.36874 (18) | 1.0057 (3) | 0.44150 (7) | 0.0462 (6) | |
C13 | 0.25550 (17) | 1.0636 (3) | 0.42285 (7) | 0.0422 (6) | |
C14 | 0.20649 (17) | 1.1483 (2) | 0.45265 (7) | 0.0295 (5) | |
C15 | 0.27387 (18) | 1.1728 (3) | 0.50129 (7) | 0.0371 (5) | |
C16 | 0.38776 (18) | 1.1166 (2) | 0.51939 (7) | 0.0364 (5) | |
O24 | −0.01767 (10) | 1.00887 (16) | 0.36198 (4) | 0.0281 (3) | |
O34 | −0.87232 (10) | 0.97300 (17) | 0.24811 (4) | 0.0300 (3) | |
C21 | −0.38049 (15) | 0.9738 (2) | 0.31639 (6) | 0.0227 (4) | |
C22 | −0.31278 (16) | 1.0319 (2) | 0.36311 (7) | 0.0299 (5) | |
C23 | −0.19401 (16) | 1.0407 (2) | 0.37855 (7) | 0.0304 (5) | |
C24 | −0.13431 (16) | 0.9927 (2) | 0.34771 (7) | 0.0239 (4) | |
C25 | −0.19980 (16) | 0.9260 (2) | 0.30190 (7) | 0.0284 (5) | |
C26 | −0.31943 (16) | 0.9188 (2) | 0.28662 (7) | 0.0271 (5) | |
C31 | −0.50877 (15) | 0.9749 (2) | 0.29867 (6) | 0.0219 (4) | |
C32 | −0.57601 (16) | 0.8747 (2) | 0.25886 (7) | 0.0274 (5) | |
C33 | −0.69556 (16) | 0.8763 (2) | 0.24208 (7) | 0.0263 (5) | |
C34 | −0.75307 (15) | 0.9792 (2) | 0.26530 (6) | 0.0230 (4) | |
C35 | −0.68938 (16) | 1.0822 (2) | 0.30442 (6) | 0.0252 (5) | |
C36 | −0.56949 (16) | 1.0804 (2) | 0.32083 (6) | 0.0250 (5) | |
N51 | 0.17838 (13) | 0.74399 (19) | 0.50313 (5) | 0.0262 (4) | |
N52 | 0.06850 (13) | 0.70099 (19) | 0.40025 (5) | 0.0277 (4) | |
N53 | 0.24003 (17) | 0.5531 (3) | 0.36793 (7) | 0.0284 (7) | 0.789 (4) |
C51 | 0.5503 (2) | 0.4668 (3) | 0.62177 (9) | 0.0249 (6) | 0.789 (4) |
C52 | 0.5220 (3) | 0.5401 (3) | 0.57540 (10) | 0.0286 (7) | 0.789 (4) |
C53 | 0.4085 (3) | 0.5892 (4) | 0.54881 (11) | 0.0283 (8) | 0.789 (4) |
C54 | 0.3209 (2) | 0.5672 (5) | 0.56779 (15) | 0.0241 (8) | 0.789 (4) |
C55 | 0.3504 (3) | 0.4962 (5) | 0.61469 (16) | 0.0315 (7) | 0.789 (4) |
C56 | 0.4622 (2) | 0.4466 (4) | 0.64074 (10) | 0.0296 (7) | 0.789 (4) |
C57 | 0.1954 (3) | 0.6093 (4) | 0.54035 (13) | 0.0249 (9) | 0.789 (4) |
C58 | 0.05573 (16) | 0.7831 (2) | 0.47860 (7) | 0.0286 (5) | |
C59 | 0.00593 (16) | 0.6660 (2) | 0.43432 (7) | 0.0292 (5) | |
C510 | 0.0369 (4) | 0.5743 (6) | 0.35862 (15) | 0.0286 (8) | 0.789 (4) |
C511 | 0.1253 (2) | 0.5974 (4) | 0.33378 (10) | 0.0290 (7) | 0.789 (4) |
C512 | 0.3295 (2) | 0.5920 (4) | 0.34708 (9) | 0.0296 (7) | 0.789 (4) |
O6 | 0.03642 (12) | 1.19090 (17) | 0.29510 (5) | 0.0328 (4)* | |
C61 | 0.5693 (6) | 0.5261 (8) | 0.6167 (3) | 0.0258 (14)* | 0.211 (4) |
C62 | 0.5313 (10) | 0.5915 (12) | 0.5692 (3) | 0.0258 (14)* | 0.211 (4) |
C63 | 0.4135 (11) | 0.6110 (14) | 0.5433 (4) | 0.0258 (14)* | 0.211 (4) |
C64 | 0.3336 (7) | 0.5651 (16) | 0.5650 (6) | 0.0258 (14)* | 0.211 (4) |
C65 | 0.3716 (8) | 0.4997 (18) | 0.6125 (6) | 0.0258 (14)* | 0.211 (4) |
C66 | 0.4894 (9) | 0.4802 (14) | 0.6384 (4) | 0.0258 (14)* | 0.211 (4) |
C67 | 0.2077 (11) | 0.5890 (17) | 0.5353 (6) | 0.0258 (14)* | 0.211 (4) |
C610 | 0.0590 (18) | 0.599 (2) | 0.3557 (6) | 0.0258 (14)* | 0.211 (4) |
C611 | 0.1323 (8) | 0.6726 (15) | 0.3286 (4) | 0.0258 (14)* | 0.211 (4) |
N63 | 0.2545 (6) | 0.6636 (10) | 0.3590 (3) | 0.0258 (14)* | 0.211 (4) |
C612 | 0.3036 (7) | 0.4950 (11) | 0.3553 (3) | 0.0258 (14)* | 0.211 (4) |
H14 | 0.0558 | 1.1518 | 0.4107 | 0.053* | |
H12 | 0.3998 | 0.9467 | 0.4202 | 0.055* | |
H13 | 0.2109 | 1.0451 | 0.3893 | 0.051* | |
H15 | 0.2417 | 1.2290 | 0.5226 | 0.044* | |
H16 | 0.4324 | 1.1376 | 0.5529 | 0.044* | |
H34 | −0.8975 | 1.0433 | 0.2641 | 0.045* | |
H22 | −0.3502 | 1.0666 | 0.3851 | 0.036* | |
H23 | −0.1517 | 1.0803 | 0.4108 | 0.036* | |
H25 | −0.1618 | 0.8849 | 0.2808 | 0.034* | |
H26 | −0.3616 | 0.8749 | 0.2548 | 0.033* | |
H32 | −0.5381 | 0.8025 | 0.2427 | 0.033* | |
H33 | −0.7384 | 0.8070 | 0.2146 | 0.032* | |
H35 | −0.7281 | 1.1548 | 0.3202 | 0.030* | |
H36 | −0.5273 | 1.1524 | 0.3478 | 0.030* | |
H51A | 0.2168 | 0.8440 | 0.5176 | 0.031* | |
H52A | 0.1469 | 0.6949 | 0.4172 | 0.033* | |
H52B | 0.0516 | 0.8125 | 0.3880 | 0.033* | |
H53A | 0.2424 | 0.4361 | 0.3755 | 0.034* | 0.789 (4) |
H52 | 0.5806 | 0.5567 | 0.5617 | 0.034* | 0.789 (4) |
H53 | 0.3906 | 0.6386 | 0.5171 | 0.034* | 0.789 (4) |
H55 | 0.2923 | 0.4820 | 0.6288 | 0.038* | 0.789 (4) |
H56 | 0.4798 | 0.3974 | 0.6724 | 0.035* | 0.789 (4) |
H57A | 0.1550 | 0.5015 | 0.5244 | 0.030* | 0.789 (4) |
H57B | 0.1595 | 0.6485 | 0.5640 | 0.030* | 0.789 (4) |
H58A | 0.0461 | 0.9071 | 0.4682 | 0.034* | |
H58B | 0.0138 | 0.7641 | 0.5015 | 0.034* | |
H59A | 0.0152 | 0.5418 | 0.4445 | 0.035* | |
H59B | −0.0777 | 0.6901 | 0.4179 | 0.035* | |
H51C | −0.0421 | 0.5986 | 0.3353 | 0.034* | 0.789 (4) |
H51D | 0.0391 | 0.4531 | 0.3708 | 0.034* | 0.789 (4) |
H51E | 0.1053 | 0.5208 | 0.3046 | 0.035* | 0.789 (4) |
H51F | 0.1245 | 0.7200 | 0.3228 | 0.035* | 0.789 (4) |
H51G | 0.3309 | 0.7197 | 0.3419 | 0.035* | 0.789 (4) |
H51H | 0.3079 | 0.5349 | 0.3146 | 0.035* | 0.789 (4) |
H61 | 0.017 (2) | 1.133 (3) | 0.3162 (7) | 0.086 (6)* | |
H62 | −0.0156 (18) | 1.267 (3) | 0.2811 (8) | 0.086 (6)* | |
H62A | 0.5859 | 0.6228 | 0.5544 | 0.031* | 0.211 (4) |
H63 | 0.3875 | 0.6557 | 0.5109 | 0.031* | 0.211 (4) |
H65 | 0.3170 | 0.4684 | 0.6272 | 0.031* | 0.211 (4) |
H66 | 0.5154 | 0.4355 | 0.6708 | 0.031* | 0.211 (4) |
H67A | 0.1802 | 0.4836 | 0.5148 | 0.031* | 0.211 (4) |
H67B | 0.1645 | 0.5960 | 0.5581 | 0.031* | 0.211 (4) |
H61A | −0.0230 | 0.5973 | 0.3335 | 0.031* | 0.211 (4) |
H61B | 0.0829 | 0.4769 | 0.3653 | 0.031* | 0.211 (4) |
H61C | 0.1185 | 0.6053 | 0.2981 | 0.031* | 0.211 (4) |
H61D | 0.1102 | 0.7957 | 0.3195 | 0.031* | 0.211 (4) |
H63A | 0.2943 | 0.7494 | 0.3495 | 0.031* | 0.1054 (18) |
H63B | 0.2627 | 0.6841 | 0.3912 | 0.031* | 0.1054 (18) |
H61E | 0.2893 | 0.4715 | 0.3203 | 0.031* | 0.211 (4) |
H61F | 0.2616 | 0.4047 | 0.3668 | 0.031* | 0.211 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O14 | 0.0293 (9) | 0.0320 (8) | 0.0356 (9) | 0.0003 (7) | 0.0009 (7) | 0.0001 (6) |
C11 | 0.0231 (11) | 0.0361 (12) | 0.0269 (11) | −0.0074 (10) | 0.0046 (10) | 0.0047 (10) |
C12 | 0.0220 (13) | 0.0916 (19) | 0.0254 (12) | −0.0050 (12) | 0.0090 (10) | 0.0005 (12) |
C13 | 0.0220 (13) | 0.0781 (17) | 0.0241 (12) | −0.0095 (11) | 0.0053 (10) | 0.0021 (11) |
C14 | 0.0229 (12) | 0.0266 (11) | 0.0337 (13) | −0.0057 (9) | 0.0034 (10) | 0.0055 (9) |
C15 | 0.0361 (14) | 0.0293 (12) | 0.0359 (13) | 0.0047 (10) | 0.0006 (11) | −0.0103 (10) |
C16 | 0.0369 (14) | 0.0288 (12) | 0.0311 (12) | −0.0009 (10) | −0.0032 (11) | −0.0063 (10) |
O24 | 0.0178 (8) | 0.0344 (8) | 0.0289 (8) | 0.0010 (6) | 0.0045 (6) | 0.0018 (6) |
O34 | 0.0198 (8) | 0.0370 (8) | 0.0314 (8) | 0.0007 (6) | 0.0069 (6) | −0.0035 (6) |
C21 | 0.0203 (11) | 0.0197 (10) | 0.0257 (11) | 0.0001 (8) | 0.0049 (9) | 0.0013 (9) |
C22 | 0.0234 (12) | 0.0383 (12) | 0.0271 (12) | 0.0041 (9) | 0.0080 (10) | −0.0052 (9) |
C23 | 0.0238 (12) | 0.0376 (12) | 0.0249 (11) | 0.0021 (9) | 0.0024 (9) | −0.0072 (10) |
C24 | 0.0188 (11) | 0.0229 (11) | 0.0269 (11) | 0.0011 (8) | 0.0041 (9) | 0.0025 (9) |
C25 | 0.0239 (12) | 0.0336 (12) | 0.0280 (11) | 0.0042 (9) | 0.0095 (10) | −0.0033 (9) |
C26 | 0.0244 (12) | 0.0289 (11) | 0.0240 (11) | 0.0001 (9) | 0.0036 (9) | −0.0037 (9) |
C31 | 0.0205 (11) | 0.0200 (10) | 0.0238 (11) | −0.0003 (8) | 0.0061 (9) | 0.0019 (9) |
C32 | 0.0240 (12) | 0.0268 (11) | 0.0301 (12) | 0.0021 (9) | 0.0079 (9) | −0.0039 (9) |
C33 | 0.0244 (12) | 0.0261 (11) | 0.0241 (11) | −0.0031 (9) | 0.0033 (9) | −0.0040 (9) |
C34 | 0.0179 (11) | 0.0258 (11) | 0.0237 (11) | 0.0000 (8) | 0.0054 (9) | 0.0058 (9) |
C35 | 0.0235 (12) | 0.0302 (11) | 0.0234 (11) | 0.0000 (9) | 0.0100 (9) | −0.0005 (9) |
C36 | 0.0231 (12) | 0.0281 (11) | 0.0209 (10) | −0.0040 (9) | 0.0041 (9) | −0.0028 (9) |
N51 | 0.0239 (10) | 0.0229 (9) | 0.0293 (10) | −0.0016 (7) | 0.0065 (8) | 0.0010 (7) |
N52 | 0.0229 (9) | 0.0294 (9) | 0.0274 (9) | 0.0043 (7) | 0.0048 (8) | 0.0013 (8) |
N53 | 0.0277 (13) | 0.0262 (14) | 0.0300 (12) | 0.0030 (10) | 0.0084 (10) | 0.0046 (10) |
C51 | 0.0299 (16) | 0.0191 (14) | 0.0244 (14) | 0.0014 (12) | 0.0080 (13) | −0.0018 (12) |
C52 | 0.0311 (17) | 0.0253 (17) | 0.0327 (18) | 0.0000 (14) | 0.0156 (14) | −0.0001 (13) |
C53 | 0.0328 (18) | 0.0289 (17) | 0.0222 (15) | 0.0039 (13) | 0.0086 (14) | 0.0030 (12) |
C54 | 0.0241 (16) | 0.0189 (13) | 0.0295 (16) | −0.0018 (11) | 0.0098 (13) | −0.0031 (11) |
C55 | 0.0302 (19) | 0.0310 (15) | 0.0347 (17) | −0.0032 (14) | 0.0134 (15) | 0.0009 (13) |
C56 | 0.034 (2) | 0.0279 (18) | 0.0257 (15) | −0.0006 (13) | 0.0085 (14) | 0.0046 (12) |
C57 | 0.0286 (17) | 0.0213 (16) | 0.0299 (17) | 0.0007 (12) | 0.0166 (13) | −0.0015 (13) |
C58 | 0.0306 (12) | 0.0269 (11) | 0.0302 (12) | 0.0040 (9) | 0.0132 (10) | 0.0022 (9) |
C59 | 0.0260 (12) | 0.0288 (11) | 0.0346 (12) | −0.0002 (9) | 0.0128 (10) | 0.0035 (9) |
C510 | 0.025 (3) | 0.033 (2) | 0.0255 (16) | −0.0017 (13) | 0.0059 (14) | −0.0041 (15) |
C511 | 0.0258 (16) | 0.0294 (17) | 0.0285 (16) | 0.0006 (13) | 0.0055 (13) | −0.0010 (14) |
C512 | 0.0320 (17) | 0.0332 (17) | 0.0250 (15) | −0.0020 (13) | 0.0120 (13) | 0.0014 (12) |
O14—C14 | 1.370 (2) | N52—C510 | 1.494 (3) |
C11—C12 | 1.393 (3) | N53—C511 | 1.455 (3) |
C11—C16 | 1.393 (3) | N53—C512 | 1.467 (3) |
C11—C11i | 1.480 (4) | C51—C52 | 1.390 (3) |
C12—C13 | 1.382 (3) | C51—C56 | 1.392 (3) |
C13—C14 | 1.383 (3) | C52—C53 | 1.393 (3) |
C14—C15 | 1.381 (3) | C53—C54 | 1.388 (3) |
C15—C16 | 1.384 (3) | C54—C55 | 1.395 (3) |
O24—C24 | 1.356 (2) | C54—C57 | 1.506 (4) |
O34—C34 | 1.378 (2) | C55—C56 | 1.373 (4) |
C21—C22 | 1.396 (2) | C58—C59 | 1.513 (2) |
C21—C26 | 1.401 (2) | C510—C511 | 1.518 (4) |
C21—C31 | 1.482 (2) | C512—C51ii | 1.510 (2) |
C22—C23 | 1.375 (3) | C61—C62 | 1.3900 |
C23—C24 | 1.399 (2) | C61—C66 | 1.3900 |
C24—C25 | 1.392 (2) | C62—C63 | 1.3900 |
C25—C26 | 1.385 (2) | C63—C64 | 1.3900 |
C31—C32 | 1.395 (2) | C64—C65 | 1.3900 |
C31—C36 | 1.405 (2) | C64—C67 | 1.499 (10) |
C32—C33 | 1.381 (2) | C65—C66 | 1.3900 |
C33—C34 | 1.386 (2) | C610—C611 | 1.506 (9) |
C34—C35 | 1.381 (2) | C611—N63 | 1.457 (8) |
C35—C36 | 1.385 (2) | N63—C612 | 1.446 (8) |
N51—C57 | 1.457 (3) | C612—C61ii | 1.499 (8) |
N51—C58 | 1.459 (2) | O6—H61 | 0.86 (2) |
N52—C59 | 1.483 (2) | O6—H62 | 0.86 (2) |
C12—C11—C16 | 115.62 (18) | C57—N51—C58 | 111.21 (18) |
C12—C11—C11i | 122.1 (2) | C59—N52—C510 | 112.30 (16) |
C16—C11—C11i | 122.2 (2) | C511—N53—C512 | 111.22 (19) |
C13—C12—C11 | 122.6 (2) | C52—C51—C56 | 118.0 (2) |
C14—C13—C12 | 120.60 (19) | C51—C52—C53 | 120.5 (2) |
O14—C14—C15 | 119.1 (2) | C54—C53—C52 | 121.2 (2) |
O14—C14—C13 | 122.8 (2) | C53—C54—C55 | 117.9 (2) |
C15—C14—C13 | 118.10 (19) | C53—C54—C57 | 124.2 (3) |
C14—C15—C16 | 120.79 (19) | C55—C54—C57 | 117.9 (3) |
C15—C16—C11 | 122.31 (19) | C56—C55—C54 | 120.9 (2) |
C22—C21—C26 | 115.68 (17) | C55—C56—C51 | 121.5 (2) |
C22—C21—C31 | 122.41 (16) | N51—C57—C54 | 113.4 (3) |
C26—C21—C31 | 121.89 (16) | N51—C58—C59 | 109.62 (15) |
C23—C22—C21 | 122.47 (17) | N52—C59—C58 | 108.34 (15) |
C22—C23—C24 | 121.30 (18) | N52—C510—C511 | 106.7 (2) |
O24—C24—C25 | 121.5 (2) | N53—C511—C510 | 109.6 (3) |
O24—C24—C23 | 121.5 (2) | N53—C512—C51ii | 114.47 (19) |
C25—C24—C23 | 117.04 (17) | C62—C61—C66 | 120.0 |
C26—C25—C24 | 121.05 (17) | C63—C62—C61 | 120.0 |
C25—C26—C21 | 122.31 (17) | C64—C63—C62 | 120.0 |
C32—C31—C36 | 116.22 (16) | C63—C64—C65 | 120.0 |
C32—C31—C21 | 122.37 (16) | C63—C64—C67 | 117.7 (12) |
C36—C31—C21 | 121.40 (16) | C65—C64—C67 | 122.3 (12) |
C33—C32—C31 | 122.50 (17) | C66—C65—C64 | 120.0 |
C32—C33—C34 | 119.97 (17) | C65—C66—C61 | 120.0 |
O34—C34—C35 | 122.9 (2) | N63—C611—C610 | 110.3 (12) |
O34—C34—C33 | 117.9 (2) | C612—N63—C611 | 111.6 (8) |
C35—C34—C33 | 119.16 (17) | N63—C612—C61ii | 116.2 (6) |
C34—C35—C36 | 120.46 (17) | H61—O6—H62 | 110 (2) |
C35—C36—C31 | 121.67 (17) | ||
C16—C11—C12—C13 | 0.5 (3) | C34—C35—C36—C31 | −0.1 (3) |
C11i—C11—C12—C13 | −179.3 (2) | C32—C31—C36—C35 | 1.0 (3) |
C11—C12—C13—C14 | −0.7 (3) | C21—C31—C36—C35 | 179.95 (16) |
C12—C13—C14—O14 | −179.84 (18) | C56—C51—C52—C53 | −0.8 (3) |
C12—C13—C14—C15 | −0.1 (3) | C51—C52—C53—C54 | 0.3 (4) |
O14—C14—C15—C16 | −179.17 (17) | C52—C53—C54—C55 | 0.8 (3) |
C13—C14—C15—C16 | 1.0 (3) | C52—C53—C54—C57 | −177.0 (2) |
C14—C15—C16—C11 | −1.3 (3) | C53—C54—C55—C56 | −1.3 (4) |
C12—C11—C16—C15 | 0.6 (3) | C57—C54—C55—C56 | 176.7 (2) |
C11i—C11—C16—C15 | −179.7 (2) | C54—C55—C56—C51 | 0.7 (4) |
C26—C21—C22—C23 | 2.2 (3) | C52—C51—C56—C55 | 0.3 (4) |
C31—C21—C22—C23 | −175.99 (17) | C58—N51—C57—C54 | −178.46 (18) |
C21—C22—C23—C24 | 0.5 (3) | C53—C54—C57—N51 | −26.6 (3) |
C22—C23—C24—O24 | 176.91 (16) | C55—C54—C57—N51 | 155.6 (3) |
C22—C23—C24—C25 | −3.7 (3) | C57—N51—C58—C59 | −90.3 (2) |
O24—C24—C25—C26 | −176.49 (16) | C510—N52—C59—C58 | 172.0 (3) |
C23—C24—C25—C26 | 4.1 (3) | N51—C58—C59—N52 | −60.84 (19) |
C24—C25—C26—C21 | −1.4 (3) | C59—N52—C510—C511 | −167.2 (2) |
C22—C21—C26—C25 | −1.8 (3) | C512—N53—C511—C510 | −173.8 (3) |
C31—C21—C26—C25 | 176.45 (16) | N52—C510—C511—N53 | 62.7 (4) |
C22—C21—C31—C32 | −161.47 (17) | C511—N53—C512—C51ii | −174.25 (19) |
C26—C21—C31—C32 | 20.4 (3) | C66—C61—C62—C63 | 0.0 |
C22—C21—C31—C36 | 19.6 (3) | C61—C62—C63—C64 | 0.0 |
C26—C21—C31—C36 | −158.48 (17) | C62—C63—C64—C65 | 0.0 |
C36—C31—C32—C33 | −0.6 (3) | C62—C63—C64—C67 | 180.0 |
C21—C31—C32—C33 | −179.59 (17) | C63—C64—C65—C66 | 0.0 |
C31—C32—C33—C34 | −0.6 (3) | C67—C64—C65—C66 | 180.0 |
C32—C33—C34—O34 | −178.26 (16) | C64—C65—C66—C61 | 0.0 |
C32—C33—C34—C35 | 1.5 (3) | C62—C61—C66—C65 | 0.0 |
O34—C34—C35—C36 | 178.59 (16) | C610—C611—N63—C612 | 85.1 (12) |
C33—C34—C35—C36 | −1.2 (3) | C611—N63—C612—C61ii | 177.1 (7) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···O24 | 0.84 | 1.77 | 2.604 (2) | 172 |
O34—H34···O6iii | 0.84 | 1.81 | 2.649 (2) | 175 |
N52—H52B···O24 | 0.92 | 1.76 | 2.662 (2) | 165 |
O6—H61···O24 | 0.86 (2) | 1.81 (2) | 2.667 (2) | 178 (2) |
O6—H62···O34iv | 0.86 (2) | 2.07 (2) | 2.923 (2) | 173 (2) |
Symmetry codes: (iii) x−1, y, z; (iv) −x−1, y+1/2, −z+1/2. |