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organic compounds
The title compound, C28H38NO3+·Cl-·CH4O, is demethoxy-buprenorphine hydrochloride (buprenorphine degradation product). Crystal structure determination has confirmed that the elimination of methanol and rearrangement with the formation of a new ring proceeds with the retention of chirality of all chiral centres of the molecule.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019410/ob6533sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019410/ob6533Isup2.hkl |
CCDC reference: 277738
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.049
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT353_ALERT_3_C Long N-H Bond (0.87A) N17 - H171 ... 1.01 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O4 - H541 ... 1.02 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H81 .. H171 .. 1.94 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 76.86 From the CIF: _reflns_number_total 5505 Count of symmetry unique reflns 3191 Completeness (_total/calc) 172.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2314 Fraction of Friedel pairs measured 0.725 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: CrysAlis RED (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.
(5R,6R,7R,9R,13R,14S)-21-Cyclopropylmethyl-6,14-endo-ethano-
2',3',4',5',7,8-hexahydro-4',4',5',5'-tetramethylfurano-
[2',3'6,7]normorphide hydrochloride methanol solvate top
Crystal data top
C28H38NO3+·Cl−·CH4O | F(000) = 1088 |
Mr = 504.11 | Dx = 1.247 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 16127 reflections |
a = 11.5861 (5) Å | θ = 5–77° |
b = 13.7665 (7) Å | µ = 1.53 mm−1 |
c = 16.8391 (8) Å | T = 295 K |
V = 2685.8 (2) Å3 | Prism, colourless |
Z = 4 | 0.32 × 0.23 × 0.14 mm |
Data collection top
Oxford Diffraction XCALIBUR diffractometer | 4754 reflections with I > 1.96u(I) |
Graphite monochromator | Rint = 0.090 |
φ and ω scans | θmax = 76.9°, θmin = 4.6° |
Absorption correction: numerical (de Meulenaer & Tompa, 1965) | h = −14→14 |
Tmin = 0.58, Tmax = 0.81 | k = −17→16 |
29111 measured reflections | l = −20→20 |
5505 independent reflections |
Refinement top
Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | Weighting scheme using Chebychev polynomial (Watkin et al., 1994;
Prince, 1982): W = [weight] * [1-(ΔF/6*σF)2]2; [weight] =
1.0/[A0*T0(x) + A1*T1(x) ··· + An-1*Tn-1(x)], where Ai are the Chebychev coefficients (13.3 -3.19 10.8) and x = F /Fmax. |
R[F2 > 2σ(F2)] = 0.041 | (Δ/σ)max = 0.000329 |
wR(F2) = 0.049 | Δρmax = 0.40 e Å−3 |
S = 1.08 | Δρmin = −0.34 e Å−3 |
4754 reflections | Extinction correction: Larson (1970) |
474 parameters | Extinction coefficient: 219 (18) |
165 restraints | Absolute structure: Flack (1983), 1563 Friedel-pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.016 (14) |
Hydrogen site location: inferred from neighbouring sites |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.79271 (15) | 0.42322 (15) | 0.71054 (12) | 0.0758 | |
O2 | 0.54608 (11) | 0.41244 (10) | 0.69597 (8) | 0.0469 | |
O3 | 0.36531 (12) | 0.37119 (12) | 0.56523 (8) | 0.0513 | |
O4 | 1.0056 (2) | 0.45182 (19) | 0.77135 (16) | 0.0948 | |
C1 | 0.71086 (16) | 0.22008 (14) | 0.84344 (11) | 0.0445 | |
C2 | 0.77885 (16) | 0.28784 (16) | 0.80291 (12) | 0.0519 | |
C3 | 0.73007 (16) | 0.35888 (16) | 0.75393 (12) | 0.0499 | |
C4 | 0.61119 (15) | 0.35964 (13) | 0.74871 (10) | 0.0398 | |
C5 | 0.42655 (15) | 0.38128 (12) | 0.70563 (10) | 0.0384 | |
C6 | 0.37579 (14) | 0.32117 (14) | 0.63834 (9) | 0.0384 | |
C7 | 0.25154 (14) | 0.30072 (12) | 0.66588 (10) | 0.0366 | |
C8 | 0.24640 (14) | 0.22244 (13) | 0.73081 (10) | 0.0379 | |
C9 | 0.38249 (14) | 0.15844 (11) | 0.84396 (9) | 0.0321 | |
C10 | 0.50929 (15) | 0.14738 (12) | 0.87152 (10) | 0.0365 | |
C11 | 0.59130 (14) | 0.22496 (12) | 0.84052 (9) | 0.0356 | |
C12 | 0.54607 (13) | 0.29968 (12) | 0.79643 (9) | 0.0339 | |
C13 | 0.42182 (13) | 0.31569 (10) | 0.78026 (9) | 0.0312 | |
C14 | 0.36955 (13) | 0.21414 (11) | 0.76494 (9) | 0.0315 | |
C15 | 0.36160 (15) | 0.36757 (12) | 0.84933 (11) | 0.0388 | |
C16 | 0.36056 (15) | 0.30855 (13) | 0.92445 (10) | 0.0390 | |
N17 | 0.31191 (11) | 0.20995 (10) | 0.90705 (8) | 0.0342 | |
C18 | 0.44919 (16) | 0.22976 (14) | 0.62722 (10) | 0.0421 | |
C19 | 0.43931 (16) | 0.16211 (12) | 0.69940 (9) | 0.0386 | |
C20 | 0.18227 (15) | 0.29402 (14) | 0.58778 (11) | 0.0433 | |
C21 | 0.24574 (17) | 0.37524 (16) | 0.53928 (11) | 0.0487 | |
C22 | 0.1890 (2) | 0.19542 (17) | 0.54720 (14) | 0.0594 | |
C23 | 0.05540 (17) | 0.31603 (18) | 0.60223 (14) | 0.0547 | |
C24 | 0.2475 (3) | 0.3620 (3) | 0.45043 (14) | 0.0794 | |
C25 | 0.2036 (3) | 0.47770 (18) | 0.5579 (2) | 0.0718 | |
C26 | 0.29374 (16) | 0.15381 (15) | 0.98258 (10) | 0.0452 | |
C27 | 0.2358 (2) | 0.05876 (15) | 0.96940 (14) | 0.0553 | |
C28 | 0.1128 (3) | 0.0588 (2) | 0.94334 (18) | 0.0733 | |
C29 | 0.1428 (3) | 0.03255 (18) | 1.02698 (18) | 0.0719 | |
C30 | 1.0443 (4) | 0.5470 (3) | 0.7811 (3) | 0.1090 | |
Cl1 | 0.07115 (4) | 0.31639 (5) | 0.90754 (4) | 0.0658 | |
H11 | 0.7489 (15) | 0.1702 (10) | 0.8739 (7) | 0.0528 (19)* | |
H21 | 0.8620 (14) | 0.2876 (11) | 0.8097 (8) | 0.0623 (19)* | |
H51 | 0.3785 (15) | 0.4404 (12) | 0.7125 (11) | 0.0463 (19)* | |
H71 | 0.2242 (15) | 0.3602 (11) | 0.6916 (10) | 0.0433 (19)* | |
H81 | 0.1899 (14) | 0.2408 (12) | 0.7725 (10) | 0.0467 (19)* | |
H82 | 0.2213 (16) | 0.1587 (11) | 0.7090 (10) | 0.0452 (19)* | |
H91 | 0.3483 (15) | 0.0931 (11) | 0.8386 (10) | 0.0393 (18)* | |
H101 | 0.5112 (15) | 0.1473 (13) | 0.9291 (9) | 0.0429 (19)* | |
H102 | 0.5370 (15) | 0.0847 (11) | 0.8536 (10) | 0.0432 (19)* | |
H151 | 0.4037 (16) | 0.4283 (12) | 0.8587 (10) | 0.0483 (19)* | |
H152 | 0.2821 (14) | 0.3832 (13) | 0.8313 (10) | 0.0472 (19)* | |
H161 | 0.3101 (15) | 0.3366 (12) | 0.9650 (10) | 0.0471 (19)* | |
H162 | 0.4366 (14) | 0.3006 (13) | 0.9475 (11) | 0.0464 (19)* | |
H181 | 0.5291 (14) | 0.2501 (13) | 0.6211 (11) | 0.0525 (19)* | |
H182 | 0.4240 (16) | 0.1952 (12) | 0.5791 (10) | 0.0494 (19)* | |
H191 | 0.5185 (14) | 0.1412 (13) | 0.7198 (10) | 0.0452 (19)* | |
H192 | 0.3965 (15) | 0.1034 (12) | 0.6840 (10) | 0.0480 (19)* | |
H221 | 0.1391 (19) | 0.1897 (18) | 0.4998 (12) | 0.0720 (19)* | |
H222 | 0.166 (2) | 0.1438 (15) | 0.5838 (13) | 0.0698 (19)* | |
H223 | 0.2691 (16) | 0.1789 (18) | 0.5289 (14) | 0.0727 (19)* | |
H231 | 0.015 (2) | 0.3211 (16) | 0.5515 (11) | 0.0660 (19)* | |
H232 | 0.046 (2) | 0.3765 (13) | 0.6315 (12) | 0.0651 (19)* | |
H233 | 0.028 (2) | 0.2604 (14) | 0.6335 (12) | 0.0669 (19)* | |
H241 | 0.1701 (18) | 0.3666 (19) | 0.4249 (17) | 0.0951 (19)* | |
H242 | 0.297 (2) | 0.4123 (17) | 0.4266 (17) | 0.0949 (19)* | |
H243 | 0.282 (2) | 0.2974 (15) | 0.4383 (18) | 0.0937 (19)* | |
H251 | 0.1310 (18) | 0.486 (2) | 0.5281 (14) | 0.0865 (19)* | |
H252 | 0.191 (2) | 0.4879 (19) | 0.6170 (11) | 0.0859 (19)* | |
H253 | 0.261 (2) | 0.5229 (18) | 0.5370 (14) | 0.0862 (19)* | |
H261 | 0.3683 (15) | 0.1410 (13) | 1.0079 (11) | 0.0546 (19)* | |
H262 | 0.2458 (16) | 0.1950 (13) | 1.0162 (11) | 0.0544 (19)* | |
H271 | 0.2818 (16) | 0.0060 (13) | 0.9470 (13) | 0.0658 (19)* | |
H281 | 0.076 (2) | 0.1238 (14) | 0.9325 (13) | 0.0882 (19)* | |
H282 | 0.087 (2) | 0.0107 (14) | 0.9033 (13) | 0.0882 (19)* | |
H291 | 0.122 (2) | 0.0775 (14) | 1.0694 (11) | 0.0857 (19)* | |
H292 | 0.133 (2) | −0.0342 (13) | 1.0454 (12) | 0.0865 (19)* | |
H171 | 0.234 (2) | 0.2237 (15) | 0.8830 (13) | 0.041 (5)* | |
H511 | 0.861 (3) | 0.427 (2) | 0.735 (2) | 0.087 (10)* | |
H541 | 1.031 (4) | 0.412 (3) | 0.819 (3) | 0.129 (15)* | |
H301 | 1.0194 | 0.5865 | 0.7344 | 0.1295* | |
H302 | 1.1303 | 0.5471 | 0.7847 | 0.1295* | |
H303 | 1.0109 | 0.5753 | 0.8307 | 0.1295* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0395 (8) | 0.1066 (14) | 0.0814 (11) | −0.0249 (9) | −0.0057 (8) | 0.0449 (11) |
O2 | 0.0350 (7) | 0.0524 (7) | 0.0534 (7) | −0.0097 (5) | −0.0042 (5) | 0.0209 (6) |
O3 | 0.0413 (7) | 0.0699 (9) | 0.0427 (7) | −0.0022 (6) | −0.0052 (5) | 0.0226 (6) |
O4 | 0.0868 (15) | 0.0982 (15) | 0.0994 (16) | −0.0272 (12) | −0.0330 (13) | 0.0202 (13) |
C1 | 0.0348 (8) | 0.0552 (10) | 0.0434 (9) | 0.0051 (8) | −0.0044 (7) | 0.0046 (8) |
C2 | 0.0284 (8) | 0.0744 (13) | 0.0528 (10) | −0.0007 (8) | −0.0018 (7) | 0.0122 (10) |
C3 | 0.0329 (9) | 0.0657 (11) | 0.0512 (10) | −0.0097 (8) | 0.0012 (7) | 0.0141 (9) |
C4 | 0.0317 (8) | 0.0455 (9) | 0.0421 (8) | −0.0044 (6) | −0.0025 (6) | 0.0074 (7) |
C5 | 0.0311 (7) | 0.0382 (8) | 0.0458 (9) | −0.0022 (6) | 0.0001 (7) | 0.0102 (7) |
C6 | 0.0356 (8) | 0.0470 (9) | 0.0325 (8) | 0.0007 (7) | −0.0002 (6) | 0.0104 (7) |
C7 | 0.0321 (7) | 0.0415 (8) | 0.0361 (8) | 0.0008 (6) | −0.0031 (6) | 0.0035 (7) |
C8 | 0.0345 (8) | 0.0442 (8) | 0.0349 (8) | −0.0049 (7) | −0.0015 (6) | 0.0033 (6) |
C9 | 0.0345 (7) | 0.0308 (7) | 0.0312 (7) | −0.0020 (6) | 0.0018 (6) | −0.0001 (6) |
C10 | 0.0375 (8) | 0.0357 (8) | 0.0363 (8) | 0.0028 (6) | 0.0001 (6) | 0.0041 (6) |
C11 | 0.0335 (8) | 0.0396 (8) | 0.0337 (7) | 0.0021 (6) | −0.0013 (6) | 0.0011 (6) |
C12 | 0.0307 (7) | 0.0353 (7) | 0.0358 (8) | −0.0017 (6) | −0.0004 (6) | −0.0013 (6) |
C13 | 0.0291 (7) | 0.0304 (7) | 0.0340 (7) | 0.0006 (6) | −0.0003 (6) | 0.0020 (6) |
C14 | 0.0332 (7) | 0.0311 (7) | 0.0301 (7) | −0.0007 (6) | 0.0005 (6) | −0.0008 (6) |
C15 | 0.0382 (8) | 0.0335 (7) | 0.0446 (9) | −0.0001 (6) | 0.0029 (7) | −0.0065 (7) |
C16 | 0.0383 (8) | 0.0389 (8) | 0.0397 (8) | −0.0042 (6) | 0.0051 (6) | −0.0091 (7) |
N17 | 0.0329 (6) | 0.0383 (6) | 0.0313 (6) | −0.0022 (5) | 0.0021 (5) | −0.0015 (5) |
C18 | 0.0394 (9) | 0.0543 (10) | 0.0327 (7) | 0.0059 (8) | 0.0035 (6) | 0.0024 (8) |
C19 | 0.0432 (9) | 0.0404 (8) | 0.0323 (7) | 0.0027 (7) | 0.0021 (6) | −0.0025 (6) |
C20 | 0.0378 (9) | 0.0505 (9) | 0.0417 (9) | 0.0017 (7) | −0.0080 (7) | 0.0046 (8) |
C21 | 0.0392 (9) | 0.0613 (11) | 0.0456 (9) | 0.0013 (8) | −0.0073 (7) | 0.0162 (8) |
C22 | 0.0683 (14) | 0.0566 (11) | 0.0532 (12) | 0.0027 (10) | −0.0167 (10) | −0.0101 (10) |
C23 | 0.0388 (9) | 0.0681 (13) | 0.0572 (11) | 0.0024 (9) | −0.0093 (8) | 0.0063 (10) |
C24 | 0.0777 (18) | 0.113 (2) | 0.0472 (12) | −0.0155 (16) | −0.0130 (11) | 0.0219 (13) |
C25 | 0.0631 (15) | 0.0551 (12) | 0.097 (2) | 0.0055 (11) | −0.0008 (14) | 0.0245 (13) |
C26 | 0.0375 (9) | 0.0636 (11) | 0.0344 (8) | −0.0024 (8) | 0.0017 (7) | 0.0078 (8) |
C27 | 0.0616 (13) | 0.0454 (10) | 0.0588 (11) | 0.0041 (9) | 0.0238 (10) | 0.0097 (9) |
C28 | 0.0692 (16) | 0.0678 (15) | 0.0830 (17) | −0.0269 (12) | 0.0154 (13) | −0.0095 (13) |
C29 | 0.0825 (18) | 0.0506 (11) | 0.0825 (17) | −0.0040 (11) | 0.0409 (15) | 0.0123 (12) |
C30 | 0.110 (3) | 0.087 (2) | 0.130 (3) | 0.002 (2) | −0.040 (2) | −0.017 (2) |
Cl1 | 0.0439 (2) | 0.0884 (4) | 0.0650 (3) | 0.0195 (3) | 0.0088 (2) | 0.0094 (3) |
Geometric parameters (Å, º) top
O1—C3 | 1.358 (2) | C16—N17 | 1.499 (2) |
O1—H511 | 0.89 (4) | C16—H161 | 0.979 (15) |
O2—C4 | 1.373 (2) | C16—H162 | 0.969 (16) |
O2—C5 | 1.459 (2) | N17—C26 | 1.503 (2) |
O3—C6 | 1.416 (2) | N17—H171 | 1.00 (2) |
O3—C21 | 1.454 (2) | C18—C19 | 1.535 (2) |
O4—C30 | 1.394 (5) | C18—H181 | 0.972 (16) |
O4—H541 | 1.02 (5) | C18—H182 | 0.984 (15) |
C1—C2 | 1.399 (3) | C19—H191 | 1.021 (15) |
C1—C11 | 1.388 (2) | C19—H192 | 0.983 (15) |
C1—H11 | 0.963 (16) | C20—C21 | 1.568 (3) |
C2—C3 | 1.399 (3) | C20—C22 | 1.522 (3) |
C2—H21 | 0.971 (16) | C20—C23 | 1.520 (3) |
C3—C4 | 1.380 (2) | C21—C24 | 1.507 (3) |
C4—C12 | 1.377 (2) | C21—C25 | 1.525 (3) |
C5—C6 | 1.522 (2) | C22—H221 | 0.989 (17) |
C5—C13 | 1.548 (2) | C22—H222 | 0.976 (17) |
C5—H51 | 0.994 (15) | C22—H223 | 1.004 (17) |
C6—C7 | 1.538 (2) | C23—H231 | 0.978 (17) |
C6—C18 | 1.530 (2) | C23—H232 | 0.974 (16) |
C7—C8 | 1.536 (2) | C23—H233 | 0.982 (17) |
C7—C20 | 1.543 (2) | C24—H241 | 0.996 (18) |
C7—H71 | 0.979 (15) | C24—H242 | 0.984 (18) |
C8—C14 | 1.542 (2) | C24—H243 | 0.996 (18) |
C8—H81 | 0.993 (15) | C25—H251 | 0.985 (18) |
C8—H82 | 0.995 (15) | C25—H252 | 1.016 (17) |
C9—C10 | 1.548 (2) | C25—H253 | 0.975 (17) |
C9—C14 | 1.543 (2) | C26—C27 | 1.487 (3) |
C9—N17 | 1.517 (2) | C26—H261 | 0.980 (16) |
C9—H91 | 0.987 (15) | C26—H262 | 0.975 (16) |
C10—C11 | 1.522 (2) | C27—C28 | 1.491 (4) |
C10—H101 | 0.970 (15) | C27—C29 | 1.493 (3) |
C10—H102 | 0.969 (15) | C27—H271 | 0.978 (17) |
C11—C12 | 1.373 (2) | C28—C29 | 1.495 (4) |
C12—C13 | 1.482 (2) | C28—H281 | 1.008 (17) |
C13—C14 | 1.545 (2) | C28—H282 | 0.992 (17) |
C13—C15 | 1.533 (2) | C29—H291 | 0.977 (17) |
C14—C19 | 1.544 (2) | C29—H292 | 0.976 (17) |
C15—C16 | 1.503 (3) | C30—H301 | 0.999 |
C15—H151 | 0.980 (15) | C30—H302 | 0.999 |
C15—H152 | 0.993 (16) | C30—H303 | 1.001 |
C3—O1—H511 | 105 (2) | C9—N17—C26 | 115.34 (13) |
C4—O2—C5 | 107.08 (12) | C16—N17—C26 | 110.67 (13) |
C6—O3—C21 | 111.20 (13) | C9—N17—H171 | 106.8 (12) |
C30—O4—H541 | 109 (3) | C16—N17—H171 | 104.1 (12) |
C2—C1—C11 | 120.84 (17) | C26—N17—H171 | 108.3 (12) |
C2—C1—H11 | 118.5 (10) | C6—C18—C19 | 111.13 (13) |
C11—C1—H11 | 120.7 (10) | C6—C18—H181 | 107.7 (11) |
C1—C2—C3 | 121.77 (17) | C19—C18—H181 | 109.3 (11) |
C1—C2—H21 | 119.9 (10) | C6—C18—H182 | 109.5 (10) |
C3—C2—H21 | 118.3 (10) | C19—C18—H182 | 109.6 (10) |
C2—C3—O1 | 123.87 (18) | H181—C18—H182 | 109.5 (13) |
C2—C3—C4 | 116.50 (17) | C14—C19—C18 | 108.87 (13) |
O1—C3—C4 | 119.60 (18) | C14—C19—H191 | 111.1 (10) |
C3—C4—O2 | 126.40 (16) | C18—C19—H191 | 111.7 (10) |
C3—C4—C12 | 120.33 (16) | C14—C19—H192 | 107.8 (10) |
O2—C4—C12 | 113.18 (15) | C18—C19—H192 | 109.1 (10) |
O2—C5—C6 | 116.34 (15) | H191—C19—H192 | 108.0 (13) |
O2—C5—C13 | 107.19 (13) | C7—C20—C21 | 99.06 (14) |
C6—C5—C13 | 105.88 (13) | C7—C20—C22 | 114.16 (16) |
O2—C5—H51 | 107.7 (10) | C21—C20—C22 | 112.23 (18) |
C6—C5—H51 | 108.4 (10) | C7—C20—C23 | 110.76 (16) |
C13—C5—H51 | 111.3 (11) | C21—C20—C23 | 113.25 (16) |
C5—C6—O3 | 114.59 (15) | C22—C20—C23 | 107.40 (17) |
C5—C6—C7 | 103.69 (13) | C20—C21—O3 | 105.25 (14) |
O3—C6—C7 | 105.72 (13) | C20—C21—C24 | 115.9 (2) |
C5—C6—C18 | 108.88 (14) | O3—C21—C24 | 106.29 (19) |
O3—C6—C18 | 109.95 (14) | C20—C21—C25 | 113.73 (19) |
C7—C6—C18 | 113.98 (15) | O3—C21—C25 | 106.21 (19) |
C6—C7—C8 | 112.29 (13) | C24—C21—C25 | 108.6 (2) |
C6—C7—C20 | 103.92 (13) | C20—C22—H221 | 113.8 (15) |
C8—C7—C20 | 122.98 (14) | C20—C22—H222 | 110.6 (15) |
C6—C7—H71 | 106.4 (11) | H221—C22—H222 | 107.2 (15) |
C8—C7—H71 | 105.0 (10) | C20—C22—H223 | 112.8 (15) |
C20—C7—H71 | 105.0 (10) | H221—C22—H223 | 105.9 (15) |
C7—C8—C14 | 106.33 (13) | H222—C22—H223 | 106.0 (15) |
C7—C8—H81 | 110.5 (10) | C20—C23—H231 | 109.9 (14) |
C14—C8—H81 | 111.4 (10) | C20—C23—H232 | 111.4 (15) |
C7—C8—H82 | 111.5 (10) | H231—C23—H232 | 109.0 (15) |
C14—C8—H82 | 110.0 (10) | C20—C23—H233 | 103.9 (15) |
H81—C8—H82 | 107.1 (13) | H231—C23—H233 | 111.8 (15) |
C10—C9—C14 | 113.55 (12) | H232—C23—H233 | 110.9 (15) |
C10—C9—N17 | 110.34 (12) | C21—C24—H241 | 114.0 (18) |
C14—C9—N17 | 108.63 (12) | C21—C24—H242 | 109.2 (18) |
C10—C9—H91 | 108.5 (10) | H241—C24—H242 | 107.6 (16) |
C14—C9—H91 | 109.6 (10) | C21—C24—H243 | 108.4 (18) |
N17—C9—H91 | 105.9 (10) | H241—C24—H243 | 109.3 (16) |
C9—C10—C11 | 114.87 (13) | H242—C24—H243 | 108.2 (16) |
C9—C10—H101 | 108.8 (10) | C21—C25—H251 | 105.8 (16) |
C11—C10—H101 | 109.2 (10) | C21—C25—H252 | 112.0 (16) |
C9—C10—H102 | 108.0 (11) | H251—C25—H252 | 111.1 (16) |
C11—C10—H102 | 108.1 (10) | C21—C25—H253 | 107.4 (17) |
H101—C10—H102 | 107.7 (13) | H251—C25—H253 | 109.0 (16) |
C10—C11—C1 | 125.25 (15) | H252—C25—H253 | 111.3 (16) |
C10—C11—C12 | 118.24 (14) | N17—C26—C27 | 112.91 (16) |
C1—C11—C12 | 115.88 (15) | N17—C26—H261 | 109.7 (11) |
C4—C12—C11 | 123.76 (15) | C27—C26—H261 | 107.7 (11) |
C4—C12—C13 | 109.63 (14) | N17—C26—H262 | 105.8 (11) |
C11—C12—C13 | 125.58 (14) | C27—C26—H262 | 109.9 (11) |
C5—C13—C12 | 101.63 (12) | H261—C26—H262 | 110.8 (13) |
C5—C13—C14 | 113.95 (13) | C26—C27—C28 | 118.4 (2) |
C12—C13—C14 | 106.07 (12) | C26—C27—C29 | 116.19 (19) |
C5—C13—C15 | 111.12 (13) | C28—C27—C29 | 60.13 (19) |
C12—C13—C15 | 111.86 (13) | C26—C27—H271 | 117.7 (10) |
C14—C13—C15 | 111.70 (13) | C28—C27—H271 | 114.1 (12) |
C8—C14—C9 | 116.61 (13) | C29—C27—H271 | 117.7 (11) |
C8—C14—C13 | 110.96 (13) | C27—C28—C29 | 60.01 (18) |
C9—C14—C13 | 105.51 (12) | C27—C28—H281 | 117.3 (13) |
C8—C14—C19 | 104.61 (13) | C29—C28—H281 | 118.9 (13) |
C9—C14—C19 | 109.58 (12) | C27—C28—H282 | 119.4 (13) |
C13—C14—C19 | 109.51 (12) | C29—C28—H282 | 123.3 (12) |
C13—C15—C16 | 112.97 (14) | H281—C28—H282 | 109.9 (14) |
C13—C15—H151 | 107.0 (10) | C28—C29—C27 | 59.86 (18) |
C16—C15—H151 | 109.3 (10) | C28—C29—H291 | 118.5 (13) |
C13—C15—H152 | 106.9 (10) | C27—C29—H291 | 120.3 (13) |
C16—C15—H152 | 111.5 (10) | C28—C29—H292 | 120.1 (13) |
H151—C15—H152 | 109.0 (13) | C27—C29—H292 | 121.0 (13) |
C15—C16—N17 | 109.15 (13) | H291—C29—H292 | 109.5 (13) |
C15—C16—H161 | 112.2 (10) | O4—C30—H301 | 109.111 |
N17—C16—H161 | 105.6 (10) | O4—C30—H302 | 109.268 |
C15—C16—H162 | 113.0 (10) | H301—C30—H302 | 109.630 |
N17—C16—H162 | 108.6 (11) | O4—C30—H303 | 109.851 |
H161—C16—H162 | 108.0 (13) | H301—C30—H303 | 109.487 |
C9—N17—C16 | 110.95 (12) | H302—C30—H303 | 109.480 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N17—H171···Cl1 | 1.00 (2) | 2.32 (2) | 3.151 (1) | 140 (2) |
O1—H511···O4 | 0.89 (4) | 1.82 (3) | 2.700 (3) | 170 (3) |
O4—H541···Cl1i | 1.02 (5) | 2.04 (5) | 3.052 (3) | 172 (4) |
Symmetry code: (i) x+1, y, z. |
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