Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026395/ob6570sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026395/ob6570Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600536805026395/ob6570sup3.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600536805026395/ob6570sup4.pdf |
CCDC reference: 283975
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.004 Å
- R factor = 0.117
- wR factor = 0.226
- Data-to-parameter ratio = 20.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.778 0.997 Tmin(prime) and Tmax expected: 0.989 0.997 RR(prime) = 0.787 Please check that your absorption correction is appropriate. RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.117 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79 PLAT082_ALERT_2_C High R1 Value .................................. 0.12 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.91 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H33 .. O2 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H34 .. O1 .. 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. C2 .. 2.87 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.
C36H58N2O3 | Z = 2 |
Mr = 566.84 | F(000) = 624.00 |
Triclinic, P1 | Dx = 1.129 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 7.514 (7) Å | Cell parameters from 2246 reflections |
b = 8.853 (8) Å | θ = 3.2–27.5° |
c = 25.21 (2) Å | µ = 0.07 mm−1 |
α = 85.15 (2)° | T = 123 K |
β = 89.36 (2)° | Platelet, yellow |
γ = 86.19 (2)° | 0.15 × 0.10 × 0.04 mm |
V = 1667 (3) Å3 |
Rigaku Saturn diffractometer | 4191 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.077 |
ω scans | θmax = 27.6° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −9→9 |
Tmin = 0.778, Tmax = 0.997 | k = −11→11 |
21767 measured reflections | l = −32→32 |
7497 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.117 | w = 1/[σ2(Fo2) + (0.0282P)2 + 2.294P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.226 | (Δ/σ)max = 0.001 |
S = 1.21 | Δρmax = 0.34 e Å−3 |
7466 reflections | Δρmin = −0.27 e Å−3 |
371 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Some low-angle reflections were excluded from the refinement, as they were probably obscured by the beam-stop. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4569 (3) | 0.3543 (3) | 0.59577 (9) | 0.0322 (6) | |
O2 | 0.9474 (3) | 0.0820 (2) | 0.41994 (8) | 0.0234 (5) | |
O3 | 0.3448 (3) | 0.9648 (2) | 0.71163 (8) | 0.0253 (5) | |
N1 | 0.5773 (3) | 0.4199 (3) | 0.56857 (10) | 0.0230 (6) | |
N2 | 0.6289 (3) | 0.5535 (3) | 0.57234 (10) | 0.0227 (5) | |
C1 | 0.6727 (4) | 0.3326 (3) | 0.52910 (11) | 0.0205 (6) | |
C2 | 0.6362 (4) | 0.1819 (4) | 0.52722 (12) | 0.0247 (7) | |
C3 | 0.7259 (4) | 0.0940 (3) | 0.49113 (12) | 0.0239 (7) | |
C4 | 0.8520 (4) | 0.1583 (3) | 0.45684 (11) | 0.0212 (6) | |
C5 | 0.8871 (4) | 0.3103 (3) | 0.45916 (12) | 0.0233 (6) | |
C6 | 0.7982 (4) | 0.3979 (3) | 0.49502 (12) | 0.0225 (6) | |
C7 | 0.9061 (4) | −0.0721 (3) | 0.41339 (12) | 0.0220 (6) | |
C8 | 1.0249 (4) | −0.1281 (3) | 0.36931 (12) | 0.0234 (6) | |
C9 | 0.9932 (4) | −0.2912 (3) | 0.35927 (12) | 0.0233 (6) | |
C10 | 1.1169 (4) | −0.3552 (3) | 0.31724 (11) | 0.0222 (6) | |
C11 | 1.0645 (4) | −0.5093 (3) | 0.30296 (12) | 0.0229 (6) | |
C12 | 1.1808 (4) | −0.5837 (3) | 0.26060 (12) | 0.0222 (6) | |
C13 | 1.1088 (4) | −0.7325 (3) | 0.24720 (12) | 0.0224 (6) | |
C14 | 1.2138 (4) | −0.8141 (3) | 0.20460 (12) | 0.0238 (6) | |
C15 | 1.1304 (4) | −0.9612 (3) | 0.19417 (12) | 0.0251 (7) | |
C16 | 1.2235 (4) | −1.0506 (3) | 0.15164 (12) | 0.0260 (7) | |
C17 | 1.1349 (5) | −1.1966 (4) | 0.14388 (13) | 0.0314 (7) | |
C18 | 1.2251 (6) | −1.2903 (4) | 0.1019 (2) | 0.0443 (9) | |
C19 | 0.5449 (4) | 0.6478 (3) | 0.60922 (11) | 0.0199 (6) | |
C20 | 0.3922 (4) | 0.6250 (3) | 0.64082 (12) | 0.0225 (6) | |
C21 | 0.3305 (4) | 0.7337 (3) | 0.67359 (12) | 0.0231 (6) | |
C22 | 0.4185 (4) | 0.8666 (3) | 0.67703 (11) | 0.0216 (6) | |
C23 | 0.5681 (4) | 0.8919 (3) | 0.64572 (12) | 0.0257 (7) | |
C24 | 0.6292 (4) | 0.7836 (3) | 0.61208 (12) | 0.0230 (6) | |
C25 | 0.4299 (4) | 1.1032 (3) | 0.71761 (12) | 0.0224 (6) | |
C26 | 0.3258 (4) | 1.1834 (3) | 0.75999 (12) | 0.0246 (7) | |
C27 | 0.4001 (4) | 1.3343 (3) | 0.77066 (12) | 0.0246 (7) | |
C28 | 0.2973 (4) | 1.4125 (3) | 0.81424 (12) | 0.0257 (7) | |
C29 | 0.3678 (4) | 1.5647 (3) | 0.82565 (13) | 0.0269 (7) | |
C30 | 0.2672 (4) | 1.6409 (3) | 0.87028 (12) | 0.0271 (7) | |
C31 | 0.3395 (4) | 1.7924 (3) | 0.88079 (13) | 0.0281 (7) | |
C32 | 0.2422 (4) | 1.8728 (4) | 0.92491 (12) | 0.0273 (7) | |
C33 | 0.3211 (5) | 2.0220 (4) | 0.93469 (13) | 0.0317 (7) | |
C34 | 0.2255 (5) | 2.1093 (4) | 0.97741 (13) | 0.0334 (8) | |
C35 | 0.3074 (6) | 2.2576 (4) | 0.9855 (2) | 0.0455 (10) | |
C36 | 0.2095 (7) | 2.3494 (5) | 1.0265 (2) | 0.0578 (12) | |
H1 | 0.5516 | 0.1397 | 0.5502 | 0.030* | |
H2 | 0.7019 | −0.0073 | 0.4898 | 0.029* | |
H3 | 0.9715 | 0.3530 | 0.4363 | 0.028* | |
H4 | 0.8218 | 0.4993 | 0.4964 | 0.027* | |
H5 | 0.7816 | −0.0753 | 0.4040 | 0.026* | |
H6 | 0.9281 | −0.1355 | 0.4462 | 0.026* | |
H7 | 1.1487 | −0.1218 | 0.3789 | 0.028* | |
H8 | 1.0021 | −0.0630 | 0.3368 | 0.028* | |
H9 | 0.8707 | −0.2959 | 0.3481 | 0.028* | |
H10 | 1.0091 | −0.3547 | 0.3924 | 0.028* | |
H11 | 1.1134 | −0.2850 | 0.2855 | 0.027* | |
H12 | 1.2382 | −0.3646 | 0.3304 | 0.027* | |
H13 | 0.9423 | −0.4984 | 0.2905 | 0.027* | |
H14 | 1.0673 | −0.5777 | 0.3351 | 0.027* | |
H15 | 1.1838 | −0.5148 | 0.2286 | 0.027* | |
H16 | 1.3018 | −0.6028 | 0.2737 | 0.027* | |
H17 | 0.9866 | −0.7121 | 0.2353 | 0.027* | |
H18 | 1.1070 | −0.8003 | 0.2795 | 0.027* | |
H19 | 1.2154 | −0.7482 | 0.1719 | 0.029* | |
H20 | 1.3360 | −0.8368 | 0.2162 | 0.029* | |
H21 | 1.1297 | −1.0258 | 0.2272 | 0.030* | |
H22 | 1.0073 | −0.9370 | 0.1837 | 0.030* | |
H23 | 1.2225 | −0.9877 | 0.1182 | 0.031* | |
H24 | 1.3470 | −1.0751 | 0.1617 | 0.031* | |
H25 | 1.0117 | −1.1713 | 0.1338 | 0.038* | |
H26 | 1.1348 | −1.2583 | 0.1776 | 0.038* | |
H27 | 1.2398 | −1.2267 | 0.0696 | 0.053* | |
H28 | 1.1526 | −1.3718 | 0.0952 | 0.053* | |
H29 | 1.3398 | −1.3314 | 0.1146 | 0.053* | |
H30 | 0.3329 | 0.5365 | 0.6396 | 0.027* | |
H31 | 0.2281 | 0.7185 | 0.6939 | 0.028* | |
H32 | 0.6268 | 0.9807 | 0.6473 | 0.031* | |
H33 | 0.7288 | 0.8014 | 0.5908 | 0.028* | |
H34 | 0.4280 | 1.1665 | 0.6842 | 0.027* | |
H35 | 0.5530 | 1.0809 | 0.7284 | 0.027* | |
H36 | 0.3278 | 1.1176 | 0.7928 | 0.030* | |
H37 | 0.2026 | 1.2018 | 0.7489 | 0.030* | |
H38 | 0.5242 | 1.3163 | 0.7810 | 0.030* | |
H39 | 0.3955 | 1.4011 | 0.7381 | 0.030* | |
H40 | 0.3025 | 1.3453 | 0.8467 | 0.031* | |
H41 | 0.1731 | 1.4292 | 0.8039 | 0.031* | |
H42 | 0.4928 | 1.5485 | 0.8351 | 0.032* | |
H43 | 0.3598 | 1.6328 | 0.7934 | 0.032* | |
H44 | 0.1422 | 1.6575 | 0.8609 | 0.033* | |
H45 | 0.2755 | 1.5734 | 0.9027 | 0.033* | |
H46 | 0.4646 | 1.7752 | 0.8901 | 0.034* | |
H47 | 0.3321 | 1.8590 | 0.8482 | 0.034* | |
H48 | 0.1176 | 1.8926 | 0.9154 | 0.033* | |
H49 | 0.2480 | 1.8063 | 0.9576 | 0.033* | |
H50 | 0.3188 | 2.0863 | 0.9016 | 0.038* | |
H51 | 0.4449 | 2.0009 | 0.9449 | 0.038* | |
H52 | 0.1014 | 2.1306 | 0.9675 | 0.040* | |
H53 | 0.2288 | 2.0461 | 1.0108 | 0.040* | |
H54 | 0.3083 | 2.3188 | 0.9517 | 0.055* | |
H55 | 0.4302 | 2.2357 | 0.9966 | 0.055* | |
H56 | 0.0832 | 2.3442 | 1.0226 | 0.069* | |
H57 | 0.2395 | 2.4533 | 1.0212 | 0.069* | |
H58 | 0.2443 | 2.3085 | 1.0616 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0349 (12) | 0.0269 (12) | 0.0373 (13) | −0.0135 (10) | 0.0146 (10) | −0.0098 (10) |
O2 | 0.0262 (11) | 0.0175 (11) | 0.0279 (11) | −0.0070 (8) | 0.0053 (9) | −0.0056 (9) |
O3 | 0.0242 (11) | 0.0216 (11) | 0.0325 (12) | −0.0090 (9) | 0.0061 (9) | −0.0111 (9) |
N1 | 0.0203 (12) | 0.0229 (13) | 0.0262 (13) | −0.0058 (10) | 0.0051 (10) | −0.0024 (10) |
N2 | 0.0211 (12) | 0.0210 (13) | 0.0271 (13) | −0.0052 (10) | 0.0025 (10) | −0.0053 (10) |
C1 | 0.0185 (13) | 0.020 (2) | 0.024 (2) | −0.0022 (11) | −0.0002 (11) | −0.0059 (12) |
C2 | 0.021 (1) | 0.028 (2) | 0.026 (2) | −0.0087 (12) | 0.0008 (12) | −0.0028 (13) |
C3 | 0.027 (2) | 0.019 (2) | 0.028 (2) | −0.0051 (12) | 0.0010 (12) | −0.0065 (12) |
C4 | 0.019 (1) | 0.025 (2) | 0.021 (1) | −0.0001 (12) | 0.0005 (11) | −0.0082 (12) |
C5 | 0.024 (2) | 0.021 (2) | 0.026 (2) | −0.0078 (12) | 0.0036 (12) | −0.0038 (12) |
C6 | 0.022 (1) | 0.019 (2) | 0.028 (2) | −0.0055 (12) | 0.0001 (12) | −0.0047 (12) |
C7 | 0.022 (1) | 0.017 (1) | 0.029 (2) | −0.0053 (11) | 0.0006 (12) | −0.0043 (12) |
C8 | 0.023 (1) | 0.018 (2) | 0.030 (2) | −0.0056 (12) | 0.0008 (12) | −0.0052 (12) |
C9 | 0.022 (1) | 0.022 (2) | 0.028 (2) | −0.0060 (12) | 0.0017 (12) | −0.0088 (12) |
C10 | 0.024 (1) | 0.022 (2) | 0.022 (2) | −0.0029 (12) | 0.0011 (12) | −0.0060 (12) |
C11 | 0.022 (1) | 0.023 (2) | 0.025 (2) | −0.0032 (12) | 0.0046 (12) | −0.0063 (12) |
C12 | 0.022 (1) | 0.021 (2) | 0.024 (2) | −0.0030 (12) | 0.0034 (12) | −0.0050 (12) |
C13 | 0.025 (2) | 0.021 (2) | 0.023 (2) | −0.0053 (12) | 0.0027 (12) | −0.0057 (12) |
C14 | 0.024 (2) | 0.022 (2) | 0.026 (2) | −0.0056 (12) | 0.0039 (12) | −0.0060 (12) |
C15 | 0.027 (2) | 0.024 (2) | 0.025 (2) | −0.0050 (13) | 0.0035 (12) | −0.0071 (12) |
C16 | 0.031 (2) | 0.020 (2) | 0.028 (2) | −0.0040 (13) | −0.0010 (13) | −0.0061 (12) |
C17 | 0.041 (2) | 0.024 (2) | 0.030 (2) | −0.003 (1) | −0.001 (1) | −0.0091 (13) |
C18 | 0.059 (3) | 0.033 (2) | 0.042 (2) | 0.003 (2) | −0.003 (2) | −0.016 (2) |
C19 | 0.024 (1) | 0.016 (1) | 0.020 (1) | −0.0002 (11) | −0.0014 (11) | −0.0046 (11) |
C20 | 0.021 (1) | 0.021 (2) | 0.027 (2) | −0.0072 (12) | 0.0025 (12) | −0.0068 (12) |
C21 | 0.019 (1) | 0.024 (2) | 0.027 (2) | −0.0090 (12) | 0.0010 (11) | −0.0027 (12) |
C22 | 0.022 (1) | 0.022 (2) | 0.022 (2) | −0.0014 (12) | −0.0016 (11) | −0.0042 (12) |
C23 | 0.025 (2) | 0.021 (2) | 0.032 (2) | −0.0069 (12) | 0.0048 (13) | −0.0064 (13) |
C24 | 0.019 (1) | 0.023 (2) | 0.027 (2) | −0.0063 (12) | 0.0022 (11) | 0.0000 (12) |
C25 | 0.023 (1) | 0.017 (2) | 0.029 (2) | −0.0046 (12) | 0.0026 (12) | −0.0069 (12) |
C26 | 0.026 (2) | 0.024 (2) | 0.025 (2) | −0.0023 (12) | −0.0016 (12) | −0.0054 (12) |
C27 | 0.025 (2) | 0.020 (2) | 0.030 (2) | −0.0046 (12) | 0.0008 (12) | −0.0043 (12) |
C28 | 0.031 (2) | 0.021 (2) | 0.027 (2) | −0.0064 (13) | 0.0022 (13) | −0.0079 (12) |
C29 | 0.032 (2) | 0.018 (2) | 0.032 (2) | −0.0047 (13) | 0.0011 (13) | −0.0034 (12) |
C30 | 0.033 (2) | 0.023 (2) | 0.026 (2) | −0.0043 (13) | 0.0015 (13) | −0.0058 (13) |
C31 | 0.032 (2) | 0.021 (2) | 0.032 (2) | −0.0044 (13) | 0.0013 (13) | −0.0076 (13) |
C32 | 0.031 (2) | 0.026 (2) | 0.026 (2) | 0.0001 (13) | 0.0023 (13) | −0.0080 (13) |
C33 | 0.040 (2) | 0.024 (2) | 0.032 (2) | −0.003 (1) | 0.001 (1) | −0.007 (1) |
C34 | 0.042 (2) | 0.030 (2) | 0.029 (2) | 0.003 (2) | −0.001 (1) | −0.009 (1) |
C35 | 0.079 (3) | 0.023 (2) | 0.036 (2) | −0.002 (2) | 0.001 (2) | −0.009 (2) |
C36 | 0.087 (3) | 0.037 (2) | 0.051 (3) | 0.008 (2) | −0.000 (2) | −0.019 (2) |
O1—N1 | 1.270 (3) | C8—H8 | 0.9700 |
O2—C4 | 1.364 (3) | C9—H9 | 0.9700 |
O2—C7 | 1.442 (3) | C9—H10 | 0.9701 |
O3—C22 | 1.370 (4) | C10—H11 | 0.9701 |
O3—C25 | 1.439 (4) | C10—H12 | 0.9699 |
N1—N2 | 1.280 (4) | C11—H13 | 0.9700 |
N1—C1 | 1.464 (4) | C11—H14 | 0.9699 |
N2—C19 | 1.417 (4) | C12—H15 | 0.9699 |
C1—C2 | 1.384 (4) | C12—H16 | 0.9701 |
C1—C6 | 1.390 (4) | C13—H17 | 0.9700 |
C2—C3 | 1.387 (4) | C13—H18 | 0.9700 |
C3—C2 | 1.387 (4) | C14—H19 | 0.9700 |
C3—C4 | 1.392 (4) | C14—H20 | 0.9700 |
C4—C3 | 1.392 (4) | C15—H21 | 0.9698 |
C4—C5 | 1.395 (4) | C15—H22 | 0.9701 |
C5—C6 | 1.379 (4) | C16—H23 | 0.9699 |
C7—C8 | 1.513 (4) | C16—H24 | 0.9701 |
C8—C9 | 1.521 (4) | C17—H25 | 0.9700 |
C9—C10 | 1.522 (4) | C17—H26 | 0.9700 |
C10—C11 | 1.518 (4) | C18—H27 | 0.9599 |
C11—C12 | 1.536 (4) | C18—H28 | 0.9599 |
C12—C13 | 1.522 (4) | C18—H29 | 0.9601 |
C13—C14 | 1.528 (4) | C20—H30 | 0.9300 |
C14—C15 | 1.525 (4) | C21—H31 | 0.9299 |
C15—C16 | 1.522 (4) | C23—H32 | 0.9300 |
C16—C17 | 1.521 (5) | C24—H33 | 0.9300 |
C17—C18 | 1.524 (5) | C25—H34 | 0.9700 |
C19—C20 | 1.405 (4) | C25—H35 | 0.9700 |
C19—C24 | 1.403 (4) | C26—H36 | 0.9700 |
C20—C21 | 1.375 (4) | C26—H37 | 0.9700 |
C21—C22 | 1.396 (4) | C27—H38 | 0.9700 |
C22—C23 | 1.386 (4) | C27—H39 | 0.9701 |
C23—C24 | 1.386 (4) | C28—H40 | 0.9698 |
C25—C26 | 1.514 (4) | C28—H41 | 0.9700 |
C26—C27 | 1.527 (4) | C29—H42 | 0.9700 |
C27—C28 | 1.523 (4) | C29—H43 | 0.9701 |
C28—C29 | 1.531 (4) | C30—H44 | 0.9699 |
C29—C30 | 1.528 (4) | C30—H45 | 0.9700 |
C30—C31 | 1.525 (4) | C31—H46 | 0.9700 |
C31—C32 | 1.524 (4) | C31—H47 | 0.9700 |
C32—C33 | 1.523 (5) | C32—H48 | 0.9699 |
C33—C34 | 1.524 (5) | C32—H49 | 0.9700 |
C34—C35 | 1.516 (5) | C33—H50 | 0.9699 |
C35—C36 | 1.522 (6) | C33—H51 | 0.9701 |
C2—H1 | 0.9300 | C34—H52 | 0.9700 |
C3—H2 | 0.9299 | C34—H53 | 0.9699 |
C5—H3 | 0.9300 | C35—H54 | 0.9699 |
C6—H4 | 0.9301 | C35—H55 | 0.9700 |
C7—H5 | 0.9700 | C36—H56 | 0.9600 |
C7—H6 | 0.9699 | C36—H57 | 0.9600 |
C8—H7 | 0.9701 | C36—H58 | 0.9600 |
O1···N2 | 2.289 (3) | C4···C20i | 3.456 (4) |
O1···C1 | 2.333 (4) | C5···C3 | 2.410 (4) |
O1···C2 | 2.693 (4) | C5···C20i | 3.286 (4) |
O1···C6i | 3.523 (3) | C6···O1i | 3.523 (3) |
O1···C19 | 2.772 (4) | C6···N1i | 3.491 (4) |
O1···C20 | 2.750 (4) | C6···C3 | 2.790 (4) |
O2···C3 | 2.438 (4) | C7···C3 | 2.828 (4) |
O2···C3ii | 3.536 (3) | C7···C9 | 2.513 (4) |
O2···C5 | 2.340 (4) | C8···C10 | 2.546 (4) |
O2···C8 | 2.381 (4) | C9···C11 | 2.517 (4) |
O2···C21i | 3.404 (3) | C10···C12 | 2.589 (4) |
O2···C24iii | 3.532 (4) | C11···C13 | 2.522 (4) |
O3···C21 | 2.341 (4) | C12···C14 | 2.574 (4) |
O3···C23 | 2.442 (4) | C13···C15 | 2.514 (4) |
O3···C26 | 2.369 (4) | C14···C16 | 2.573 (4) |
N1···C2 | 2.441 (4) | C15···C17 | 2.527 (5) |
N1···C6 | 2.486 (4) | C16···C18 | 2.554 (5) |
N1···C6i | 3.491 (4) | C19···C21 | 2.407 (4) |
N1···C19 | 2.336 (4) | C19···C22 | 2.803 (4) |
N1···C20 | 2.952 (4) | C19···C23 | 2.437 (4) |
N1···C24 | 3.535 (4) | C20···C4i | 3.456 (4) |
N2···C1 | 2.322 (4) | C20···C5i | 3.286 (4) |
N2···C1i | 3.476 (4) | C20···C22 | 2.416 (4) |
N2···C2 | 3.567 (4) | C20···C23 | 2.795 (4) |
N2···C6 | 2.735 (4) | C20···C24 | 2.408 (4) |
N2···C20 | 2.552 (4) | C21···O2i | 3.404 (3) |
N2···C24 | 2.345 (4) | C21···C23 | 2.404 (4) |
C1···N2i | 3.476 (4) | C21···C24 | 2.752 (4) |
C1···C3 | 2.400 (4) | C22···C24 | 2.391 (4) |
C1···C4 | 2.767 (4) | C22···C25 | 2.414 (4) |
C1···C5 | 2.387 (4) | C23···C25 | 2.852 (4) |
C2···C4 | 2.403 (4) | C24···O2iii | 3.532 (4) |
C2···C5 | 2.770 (4) | C25···C27 | 2.534 (4) |
C2···C6 | 2.413 (4) | C26···C28 | 2.536 (4) |
C3···O2 | 2.438 (4) | C27···C29 | 2.558 (4) |
C3···O2ii | 3.536 (3) | C28···C30 | 2.560 (4) |
C3···C1 | 2.400 (4) | C29···C31 | 2.540 (5) |
C3···C5 | 2.410 (4) | C30···C32 | 2.562 (4) |
C3···C6 | 2.790 (4) | C31···C33 | 2.534 (5) |
C3···C7 | 2.828 (4) | C32···C34 | 2.565 (5) |
C4···C6 | 2.411 (4) | C33···C35 | 2.533 (5) |
C4···C7 | 2.404 (4) | C34···C36 | 2.544 (5) |
O1—N1—N2 | 127.6 (3) | C13—C14—H20 | 109.4597 |
O1—N1—C1 | 117.0 (2) | H18—C13—H17 | 107.5102 |
O2—C4—C3 | 124.3 (3) | H19—C14—C15 | 109.4638 |
O2—C4—C5 | 116.0 (2) | H20—C14—C15 | 109.4650 |
C7—O2—C4 | 117.9 (2) | C14—C15—H21 | 108.4867 |
O2—C7—C8 | 107.3 (2) | C14—C15—H22 | 108.4806 |
O3—C22—C21 | 115.6 (2) | H20—C14—H19 | 108.0454 |
O3—C22—C23 | 124.8 (3) | H21—C15—C16 | 108.4770 |
C25—O3—C22 | 118.5 (2) | H22—C15—C16 | 108.4644 |
O3—C25—C26 | 106.6 (2) | C15—C16—H23 | 109.1431 |
C1—N1—N2 | 115.4 (2) | C15—C16—H24 | 109.1277 |
N1—N2—C19 | 119.9 (2) | H22—C15—H21 | 107.5119 |
N1—C1—C2 | 118.0 (2) | H23—C16—C17 | 109.1489 |
N1—C1—C6 | 121.1 (3) | H24—C16—C17 | 109.1457 |
N2—C19—C20 | 129.4 (3) | C16—C17—H25 | 108.7525 |
N2—C19—C24 | 112.5 (2) | C16—C17—H26 | 108.7508 |
C1—C2—C3 | 120.0 (3) | H24—C16—H23 | 107.8695 |
C6—C1—C2 | 120.9 (3) | H25—C17—C18 | 108.7585 |
C1—C6—C5 | 119.1 (3) | H26—C17—C18 | 108.7576 |
C2—C3—C4 | 119.6 (3) | C17—C18—H27 | 109.4721 |
C3—C4—C5 | 119.7 (3) | C17—C18—H28 | 109.4634 |
C4—C5—C6 | 120.7 (3) | C17—C18—H29 | 109.4594 |
C7—C8—C9 | 111.8 (2) | H26—C17—H25 | 107.6467 |
C8—C9—C10 | 113.6 (2) | H28—C18—H27 | 109.4816 |
C9—C10—C11 | 111.8 (2) | H29—C18—H27 | 109.4797 |
C10—C11—C12 | 116.0 (2) | H29—C18—H28 | 109.4712 |
C11—C12—C13 | 111.2 (2) | C19—C20—H30 | 120.0193 |
C12—C13—C14 | 115.2 (2) | C19—C24—H33 | 119.0983 |
C13—C14—C15 | 110.9 (2) | H30—C20—C21 | 120.0230 |
C14—C15—C16 | 115.2 (3) | C20—C21—H31 | 119.3307 |
C15—C16—C17 | 112.3 (3) | H31—C21—C22 | 119.3420 |
C16—C17—C18 | 114.0 (3) | C22—C23—H32 | 120.3781 |
C19—C20—C21 | 120.0 (3) | H32—C23—C24 | 120.3646 |
C24—C19—C20 | 118.0 (3) | C23—C24—H33 | 119.0917 |
C19—C24—C23 | 121.8 (3) | H34—C25—C26 | 110.3935 |
C20—C21—C22 | 121.3 (3) | H35—C25—C26 | 110.4027 |
C21—C22—C23 | 119.6 (3) | C25—C26—H36 | 109.0157 |
C22—C23—C24 | 119.3 (3) | C25—C26—H37 | 109.0242 |
C25—C26—C27 | 112.8 (2) | H35—C25—H34 | 108.6077 |
C26—C27—C28 | 112.5 (2) | H36—C26—C27 | 109.0152 |
C27—C28—C29 | 113.8 (3) | H37—C26—C27 | 109.0185 |
C28—C29—C30 | 113.6 (3) | C26—C27—H38 | 109.1000 |
C29—C30—C31 | 112.6 (3) | C26—C27—H39 | 109.0920 |
C30—C31—C32 | 114.3 (3) | H37—C26—H36 | 107.7953 |
C31—C32—C33 | 112.5 (3) | H38—C27—C28 | 109.0998 |
C32—C33—C34 | 114.7 (3) | H39—C27—C28 | 109.1089 |
C33—C34—C35 | 112.9 (3) | C27—C28—H40 | 108.7988 |
C34—C35—C36 | 113.7 (3) | C27—C28—H41 | 108.7985 |
O2—C7—H5 | 110.2477 | H39—C27—H38 | 107.8435 |
O2—C7—H6 | 110.2514 | H40—C28—C29 | 108.8119 |
O3—C25—H34 | 110.4056 | H41—C28—C29 | 108.8054 |
O3—C25—H35 | 110.3980 | C28—C29—H42 | 108.8378 |
C1—C2—H1 | 120.0074 | C28—C29—H43 | 108.8424 |
C1—C6—H4 | 120.4625 | H41—C28—H40 | 107.6817 |
H1—C2—C3 | 120.0118 | H42—C29—C30 | 108.8440 |
C2—C3—H2 | 120.1772 | H43—C29—C30 | 108.8344 |
H2—C3—C4 | 120.1857 | C29—C30—H44 | 109.0669 |
C4—C5—H3 | 119.6279 | C29—C30—H45 | 109.0630 |
H3—C5—C6 | 119.6298 | H43—C29—H42 | 107.6875 |
C5—C6—H4 | 120.4843 | H44—C30—C31 | 109.0661 |
H5—C7—C8 | 110.2449 | H45—C30—C31 | 109.0653 |
H6—C7—C8 | 110.2462 | C30—C31—H46 | 108.6732 |
C7—C8—H7 | 109.2552 | C30—C31—H47 | 108.6745 |
C7—C8—H8 | 109.2629 | H45—C30—H44 | 107.8278 |
H6—C7—H5 | 108.5223 | H46—C31—C32 | 108.6744 |
H7—C8—C9 | 109.2657 | H47—C31—C32 | 108.6737 |
H8—C8—C9 | 109.2588 | C31—C32—H48 | 109.1071 |
C8—C9—H9 | 108.8568 | C31—C32—H49 | 109.0990 |
C8—C9—H10 | 108.8559 | H47—C31—H46 | 107.6004 |
H8—C8—H7 | 107.9371 | H48—C32—C33 | 109.0950 |
H9—C9—C10 | 108.8564 | H49—C32—C33 | 109.0940 |
H10—C9—C10 | 108.8490 | C32—C33—H50 | 108.5927 |
C9—C10—H11 | 109.2480 | C32—C33—H51 | 108.5919 |
C9—C10—H12 | 109.2626 | H49—C32—H48 | 107.8307 |
H10—C9—H9 | 107.7048 | H50—C33—C34 | 108.5878 |
H11—C10—C11 | 109.2480 | H51—C33—C34 | 108.5769 |
H12—C10—C11 | 109.2475 | C33—C34—H52 | 109.0005 |
C10—C11—H13 | 108.2851 | C33—C34—H53 | 109.0120 |
C10—C11—H14 | 108.2874 | H51—C33—H50 | 107.5641 |
H12—C10—H11 | 107.9210 | H52—C34—C35 | 109.0041 |
H13—C11—C12 | 108.2784 | H53—C34—C35 | 109.0111 |
H14—C11—C12 | 108.2902 | C34—C35—H54 | 108.8239 |
C11—C12—H15 | 109.4027 | C34—C35—H55 | 108.8176 |
C11—C12—H16 | 109.3899 | H53—C34—H52 | 107.7944 |
H14—C11—H13 | 107.3979 | H54—C35—C36 | 108.8172 |
H15—C12—C13 | 109.4063 | H55—C35—C36 | 108.8238 |
H16—C12—C13 | 109.3979 | C35—C36—H56 | 109.4735 |
C12—C13—H17 | 108.4765 | C35—C36—H57 | 109.4680 |
C12—C13—H18 | 108.4854 | C35—C36—H58 | 109.4660 |
H16—C12—H15 | 108.0163 | H55—C35—H54 | 107.6848 |
H17—C13—C14 | 108.4658 | H57—C36—H56 | 109.4728 |
H18—C13—C14 | 108.4668 | H58—C36—H56 | 109.4743 |
C13—C14—H19 | 109.4580 | H58—C36—H57 | 109.4727 |
C7—O2—C4—C3 | 4.6 (4) | C9—C10—C11—C12 | 179.8 (2) |
C7—O2—C4—C5 | −175.5 (2) | C10—C11—C12—C13 | −176.5 (2) |
C4—O2—C7—C8 | 178.1 (2) | C11—C12—C13—C14 | 179.0 (2) |
C25—O3—C22—C21 | 179.3 (2) | C12—C13—C14—C15 | −179.9 (2) |
C25—O3—C22—C23 | −1.9 (4) | C13—C14—C15—C16 | 179.1 (2) |
C22—O3—C25—C26 | −177.0 (2) | C14—C15—C16—C17 | 179.2 (2) |
O1—N1—N2—C19 | −2.0 (4) | C15—C16—C17—C18 | −179.5 (3) |
C1—N1—N2—C19 | 179.8 (2) | N2—C19—C20—C21 | −178.7 (3) |
O1—N1—C1—C2 | −5.3 (4) | C24—C19—C20—C21 | −0.5 (4) |
O1—N1—C1—C6 | 175.7 (3) | N2—C19—C24—C23 | 179.9 (2) |
N2—N1—C1—C2 | 173.1 (2) | C20—C19—C24—C23 | 1.4 (4) |
N2—N1—C1—C6 | −5.9 (4) | C19—C20—C21—C22 | −1.1 (4) |
N1—N2—C19—C20 | −7.8 (4) | C20—C21—C22—O3 | −179.2 (3) |
N1—N2—C19—C24 | 173.9 (2) | C20—C21—C22—C23 | 1.9 (4) |
N1—C1—C2—C3 | −178.8 (3) | O3—C22—C23—C24 | −179.8 (3) |
C6—C1—C2—C3 | 0.2 (4) | C21—C22—C23—C24 | −1.0 (4) |
N1—C1—C6—C5 | 178.8 (3) | C22—C23—C24—C19 | −0.7 (4) |
C2—C1—C6—C5 | −0.2 (4) | O3—C25—C26—C27 | −179.6 (2) |
C1—C2—C3—C4 | −0.2 (4) | C25—C26—C27—C28 | −178.7 (2) |
C2—C3—C4—O2 | −180.0 (2) | C26—C27—C28—C29 | −179.6 (2) |
C2—C3—C4—C5 | 0.1 (3) | C27—C28—C29—C30 | −178.6 (2) |
O2—C4—C5—C6 | 180.0 (3) | C28—C29—C30—C31 | −179.9 (2) |
C3—C4—C5—C6 | −0.1 (3) | C29—C30—C31—C32 | 179.7 (2) |
C4—C5—C6—C1 | 0.2 (4) | C30—C31—C32—C33 | 179.0 (3) |
O2—C7—C8—C9 | 179.6 (2) | C31—C32—C33—C34 | 178.4 (3) |
C7—C8—C9—C10 | −176.9 (2) | C32—C33—C34—C35 | −179.5 (3) |
C8—C9—C10—C11 | −172.1 (2) | C33—C34—C35—C36 | 177.8 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H33···O2iii | 0.93 | 2.71 | 3.532 (4) | 148 (1) |
C25—H34···O1iv | 0.97 | 2.68 | 3.648 (4) | 173 (1) |
C8—H7···C2ii | 0.97 | 2.87 | 3.646 (4) | 137 (1) |
Symmetry codes: (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x, y+1, z. |
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