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The structure of
N-triphenylacetyl-
L-tyrosine (C
29H
25NO
4,
L-
TrCOTyr) is characterized by the presence of both donors and acceptors of classical hydrogen bonds. At the same time, the molecule contains a sterically demanding and hydrophobic trityl group capable of participating in π-electron interactions. Due to its large volume, the trityl group may favour the formation of structural voids in the crystals, which can be filled with guest molecules. In this article, we present the crystal structures of a series of
N-triphenylacetyl-
L-tyrosine solvates with chloroform, namely,
L-
TrCOTyr·CHCl
3 (
I) and
L-
TrCOTyr·1.5CHCl
3 (
III), and dichloromethane, namely,
L-
TrCOTyr·CH
2Cl
2 (
II) and
L-
TrCOTyr·0.1CH
2Cl
2 (
IV). To complement the topic, we also decided to use the racemic amide
N-triphenylacetyl-
DL-tyrosine (
rac-
TrCOTyr) and recrystallized it from a mixture of chloroform and dichloromethane. As a result,
rac-
TrCOTyr·1.5CHCl
3 (
V) was obtained. In the crystal structures, the amide molecules interact with each other
via O—H
O hydrogen bonds. Noticeably, the amide N—H group does not participate in the formation of intermolecular hydrogen bonds. Channels are formed between the
TrCOTyr molecules and these are filled with solvent molecules. Additionally, in the crystals of
III and
V, there are structural voids that are occupied by chloroform molecules. Structure analysis has shown that solvates
I and
II are isostructural. Upon loss of solvent, the solvates transform into the solvent-free form of
TrCOTyr, as confirmed by thermogravimetric analysis, differential scanning calorimetry and powder X-ray diffraction.
Supporting information
CCDC references: 2117317; 2117316; 2117315; 2117314; 2117313
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).
N-Triphenylacetyl-
L-tyrosine chloroform monosolvate (I)
top
Crystal data top
C29H25NO4·CHCl3 | F(000) = 592 |
Mr = 570.87 | Dx = 1.357 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 10.0732 (3) Å | Cell parameters from 17066 reflections |
b = 10.0051 (2) Å | θ = 3.1–75.4° |
c = 14.7474 (4) Å | µ = 3.27 mm−1 |
β = 109.945 (3)° | T = 130 K |
V = 1397.14 (6) Å3 | Needle, colourless |
Z = 2 | 0.22 × 0.05 × 0.03 mm |
Data collection top
Rigaku SuperNova Single Source diffractometer with an Atlas detector | 4905 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 4842 reflections with I > 2σ(I) |
Detector resolution: 10.5357 pixels mm-1 | Rint = 0.050 |
ω scans | θmax = 66.6°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | h = −11→11 |
Tmin = 0.408, Tmax = 1.000 | k = −11→11 |
18782 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0866P)2 + 0.5933P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max = 0.004 |
S = 1.03 | Δρmax = 0.59 e Å−3 |
4905 reflections | Δρmin = −0.41 e Å−3 |
399 parameters | Absolute structure: Flack x determined using 2221 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
35 restraints | Absolute structure parameter: 0.003 (12) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The diffraction data for all monocrystals were collected at 130 K
with an Oxford Diffraction SuperNova diffractometer using Cu Kα radiation
(λ = 1.54184 Å). The intensity data were collected and processed with
the use of CrysAlis PRO software (1.171.40.67a). The structures were
solved by
direct methods with the program SHELXT2018 (Sheldrick, 2015b) and
refined by full-matrix least-squares method on F2 with SHELXL2018
(Sheldrick, 2015a). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 1.1584 (10) | 0.1410 (12) | 0.5439 (8) | 0.061 (3) | 0.293 (4) |
Cl2 | 0.8582 (10) | 0.1311 (10) | 0.4498 (7) | 0.056 (2) | 0.293 (4) |
Cl3 | 0.9907 (9) | −0.0337 (8) | 0.6152 (6) | 0.082 (2) | 0.293 (4) |
C37 | 0.9963 (7) | 0.1180 (6) | 0.5591 (4) | 0.050 (2) | 0.293 (4) |
H37 | 0.984733 | 0.190820 | 0.602198 | 0.061* | 0.293 (4) |
Cl1A | 1.1562 (6) | 0.1829 (8) | 0.5449 (6) | 0.045 (2) | 0.336 (4) |
Cl2A | 0.8526 (8) | 0.1737 (8) | 0.4578 (7) | 0.0390 (19) | 0.336 (4) |
Cl3A | 1.0029 (7) | −0.0488 (7) | 0.5717 (6) | 0.0574 (18) | 0.336 (4) |
C37A | 0.9988 (5) | 0.1196 (6) | 0.5583 (4) | 0.050 (2) | 0.336 (4) |
H37A | 0.989404 | 0.160245 | 0.617738 | 0.061* | 0.336 (4) |
Cl1B | 1.1380 (10) | 0.2328 (13) | 0.5580 (11) | 0.195 (8) | 0.371 (4) |
Cl2B | 0.8346 (8) | 0.2175 (9) | 0.4617 (7) | 0.072 (2) | 0.371 (4) |
Cl3B | 0.9940 (9) | −0.0222 (11) | 0.5417 (7) | 0.114 (4) | 0.371 (4) |
C37B | 0.9812 (8) | 0.1519 (9) | 0.5541 (5) | 0.073 (6) | 0.371 (4) |
H37B | 0.966652 | 0.168984 | 0.616817 | 0.087* | 0.371 (4) |
O1 | 1.1595 (3) | 0.9555 (3) | 1.01420 (18) | 0.0291 (5) | |
H1 | 1.187217 | 1.034282 | 1.028915 | 0.044* | |
O2 | 0.9909 (3) | 1.0568 (3) | 0.8940 (2) | 0.0346 (6) | |
O3 | 0.7693 (3) | 0.7058 (3) | 0.93487 (16) | 0.0262 (5) | |
O4 | 0.9212 (3) | 0.2269 (3) | 0.7372 (2) | 0.0387 (7) | |
H4 | 0.948124 | 0.174996 | 0.784730 | 0.058* | |
N1 | 0.8553 (3) | 0.8198 (3) | 0.83552 (19) | 0.0215 (6) | |
H1A | 0.835896 | 0.859254 | 0.779163 | 0.026* | |
C1 | 1.0483 (3) | 0.9560 (4) | 0.9351 (2) | 0.0239 (7) | |
C2 | 1.0011 (3) | 0.8163 (3) | 0.8999 (2) | 0.0220 (6) | |
H2 | 1.007470 | 0.758649 | 0.956600 | 0.026* | |
C3 | 1.0985 (4) | 0.7583 (3) | 0.8486 (3) | 0.0242 (7) | |
H3A | 1.090953 | 0.813291 | 0.791238 | 0.029* | |
H3B | 1.197707 | 0.761498 | 0.892769 | 0.029* | |
C4 | 1.0585 (4) | 0.6156 (3) | 0.8179 (2) | 0.0235 (7) | |
C5 | 0.9743 (4) | 0.5844 (4) | 0.7239 (3) | 0.0285 (7) | |
H5 | 0.946926 | 0.653457 | 0.676868 | 0.034* | |
C6 | 0.9296 (4) | 0.4547 (4) | 0.6974 (3) | 0.0312 (8) | |
H6 | 0.871496 | 0.435277 | 0.633057 | 0.037* | |
C7 | 0.9703 (4) | 0.3531 (4) | 0.7658 (3) | 0.0274 (7) | |
C8 | 1.0579 (4) | 0.3818 (4) | 0.8593 (3) | 0.0267 (7) | |
H8 | 1.088428 | 0.312451 | 0.905786 | 0.032* | |
C9 | 1.0999 (4) | 0.5118 (3) | 0.8839 (2) | 0.0248 (7) | |
H9 | 1.159137 | 0.530965 | 0.948069 | 0.030* | |
C10 | 0.5962 (3) | 0.7787 (3) | 0.7841 (2) | 0.0201 (6) | |
C11 | 0.5981 (3) | 0.8353 (3) | 0.6867 (2) | 0.0218 (7) | |
C12 | 0.5682 (4) | 0.7591 (4) | 0.6044 (3) | 0.0298 (8) | |
H12 | 0.542578 | 0.667969 | 0.605741 | 0.036* | |
C13 | 0.5752 (4) | 0.8142 (5) | 0.5186 (3) | 0.0363 (8) | |
H13 | 0.552862 | 0.760384 | 0.462268 | 0.044* | |
C14 | 0.6142 (4) | 0.9455 (4) | 0.5153 (3) | 0.0357 (8) | |
H14 | 0.620113 | 0.982055 | 0.457364 | 0.043* | |
C15 | 0.6445 (4) | 1.0234 (4) | 0.5970 (3) | 0.0303 (8) | |
H15 | 0.672133 | 1.113912 | 0.595296 | 0.036* | |
C16 | 0.6351 (4) | 0.9710 (4) | 0.6820 (3) | 0.0261 (7) | |
H16 | 0.653604 | 1.026527 | 0.737132 | 0.031* | |
C17 | 0.7489 (3) | 0.7656 (3) | 0.8580 (2) | 0.0199 (6) | |
C21 | 0.5122 (4) | 0.8761 (3) | 0.8265 (3) | 0.0238 (7) | |
C22 | 0.3913 (4) | 0.9392 (4) | 0.7625 (3) | 0.0286 (7) | |
H22 | 0.362006 | 0.919600 | 0.695463 | 0.034* | |
C23 | 0.3149 (4) | 1.0292 (4) | 0.7962 (3) | 0.0339 (9) | |
H23 | 0.233269 | 1.070385 | 0.752321 | 0.041* | |
C24 | 0.3565 (4) | 1.0598 (4) | 0.8938 (3) | 0.0369 (9) | |
H24 | 0.306272 | 1.124522 | 0.916400 | 0.044* | |
C25 | 0.4713 (5) | 0.9955 (5) | 0.9571 (3) | 0.0414 (10) | |
H25 | 0.498995 | 1.014048 | 1.024210 | 0.050* | |
C26 | 0.5472 (4) | 0.9031 (4) | 0.9236 (3) | 0.0340 (8) | |
H26 | 0.624772 | 0.857796 | 0.968544 | 0.041* | |
C31 | 0.5366 (3) | 0.6351 (3) | 0.7727 (2) | 0.0211 (6) | |
C32 | 0.3990 (4) | 0.6072 (4) | 0.7654 (3) | 0.0266 (7) | |
H32 | 0.337897 | 0.677713 | 0.768987 | 0.032* | |
C33 | 0.3496 (4) | 0.4762 (4) | 0.7527 (3) | 0.0328 (8) | |
H33 | 0.254721 | 0.458237 | 0.747554 | 0.039* | |
C34 | 0.4370 (4) | 0.3715 (4) | 0.7476 (3) | 0.0345 (9) | |
H34 | 0.403029 | 0.282218 | 0.739670 | 0.041* | |
C35 | 0.5755 (4) | 0.3995 (4) | 0.7544 (3) | 0.0334 (8) | |
H35 | 0.636748 | 0.329060 | 0.750819 | 0.040* | |
C36 | 0.6236 (4) | 0.5298 (4) | 0.7662 (3) | 0.0289 (8) | |
H36 | 0.717930 | 0.548085 | 0.769994 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.077 (5) | 0.070 (6) | 0.039 (3) | 0.016 (4) | 0.024 (3) | 0.012 (3) |
Cl2 | 0.059 (3) | 0.068 (5) | 0.043 (3) | 0.003 (3) | 0.019 (2) | 0.002 (3) |
Cl3 | 0.100 (5) | 0.066 (4) | 0.060 (5) | −0.012 (3) | −0.001 (4) | 0.017 (3) |
C37 | 0.058 (6) | 0.062 (5) | 0.029 (4) | 0.003 (4) | 0.012 (4) | 0.003 (3) |
Cl1A | 0.025 (2) | 0.076 (6) | 0.029 (2) | −0.023 (3) | 0.0008 (19) | 0.010 (3) |
Cl2A | 0.032 (2) | 0.048 (3) | 0.038 (2) | −0.006 (2) | 0.0135 (17) | 0.000 (2) |
Cl3A | 0.049 (2) | 0.079 (3) | 0.036 (4) | −0.023 (2) | 0.004 (2) | −0.003 (3) |
C37A | 0.058 (6) | 0.062 (5) | 0.029 (4) | 0.003 (4) | 0.012 (4) | 0.003 (3) |
Cl1B | 0.086 (6) | 0.252 (16) | 0.205 (12) | −0.072 (8) | −0.007 (6) | 0.023 (10) |
Cl2B | 0.057 (3) | 0.096 (6) | 0.059 (3) | −0.014 (3) | 0.015 (2) | 0.004 (4) |
Cl3B | 0.107 (5) | 0.180 (8) | 0.062 (5) | 0.030 (5) | 0.038 (4) | −0.018 (4) |
C37B | 0.059 (9) | 0.093 (11) | 0.076 (11) | −0.004 (8) | 0.036 (8) | −0.019 (8) |
O1 | 0.0264 (12) | 0.0259 (12) | 0.0310 (12) | −0.0046 (10) | 0.0047 (10) | −0.0068 (10) |
O2 | 0.0388 (15) | 0.0198 (12) | 0.0391 (14) | −0.0014 (11) | 0.0054 (12) | 0.0026 (10) |
O3 | 0.0266 (12) | 0.0268 (12) | 0.0241 (11) | −0.0015 (10) | 0.0072 (9) | 0.0070 (10) |
O4 | 0.0581 (19) | 0.0238 (13) | 0.0332 (14) | −0.0115 (12) | 0.0144 (13) | −0.0055 (11) |
N1 | 0.0215 (13) | 0.0199 (12) | 0.0220 (12) | −0.0024 (11) | 0.0060 (11) | 0.0025 (11) |
C1 | 0.0210 (15) | 0.0258 (16) | 0.0255 (16) | −0.0019 (14) | 0.0085 (13) | −0.0020 (14) |
C2 | 0.0184 (15) | 0.0201 (15) | 0.0253 (15) | −0.0013 (12) | 0.0046 (12) | 0.0023 (13) |
C3 | 0.0231 (17) | 0.0201 (15) | 0.0306 (17) | −0.0034 (13) | 0.0109 (14) | −0.0006 (13) |
C4 | 0.0240 (16) | 0.0225 (16) | 0.0274 (17) | −0.0001 (13) | 0.0134 (13) | −0.0006 (13) |
C5 | 0.0321 (18) | 0.0273 (18) | 0.0266 (17) | −0.0024 (14) | 0.0108 (14) | 0.0012 (14) |
C6 | 0.0375 (19) | 0.0327 (19) | 0.0223 (16) | −0.0026 (16) | 0.0089 (14) | −0.0016 (15) |
C7 | 0.0355 (19) | 0.0188 (16) | 0.0322 (18) | −0.0042 (14) | 0.0172 (15) | −0.0045 (13) |
C8 | 0.0332 (18) | 0.0222 (16) | 0.0288 (17) | 0.0014 (13) | 0.0160 (14) | 0.0011 (13) |
C9 | 0.0258 (17) | 0.0253 (17) | 0.0238 (16) | 0.0000 (13) | 0.0090 (13) | −0.0019 (13) |
C10 | 0.0221 (16) | 0.0181 (15) | 0.0212 (15) | −0.0031 (12) | 0.0089 (12) | 0.0015 (12) |
C11 | 0.0173 (14) | 0.0260 (17) | 0.0229 (16) | 0.0013 (12) | 0.0078 (12) | 0.0045 (13) |
C12 | 0.0328 (19) | 0.0278 (18) | 0.0286 (18) | −0.0043 (15) | 0.0103 (15) | −0.0009 (15) |
C13 | 0.041 (2) | 0.044 (2) | 0.0253 (17) | −0.0078 (18) | 0.0125 (15) | −0.0059 (17) |
C14 | 0.0356 (19) | 0.043 (2) | 0.0297 (18) | 0.0006 (18) | 0.0125 (15) | 0.0103 (17) |
C15 | 0.0328 (19) | 0.0263 (18) | 0.0330 (18) | 0.0005 (14) | 0.0128 (15) | 0.0081 (14) |
C16 | 0.0252 (16) | 0.0243 (17) | 0.0267 (17) | 0.0022 (13) | 0.0060 (13) | 0.0028 (14) |
C17 | 0.0224 (16) | 0.0152 (13) | 0.0229 (15) | −0.0008 (12) | 0.0086 (13) | −0.0002 (12) |
C21 | 0.0261 (16) | 0.0170 (15) | 0.0313 (17) | −0.0015 (12) | 0.0138 (14) | 0.0024 (13) |
C22 | 0.0288 (17) | 0.0276 (18) | 0.0309 (17) | 0.0021 (14) | 0.0121 (14) | 0.0043 (14) |
C23 | 0.0309 (19) | 0.0248 (18) | 0.050 (2) | 0.0046 (15) | 0.0191 (17) | 0.0103 (17) |
C24 | 0.040 (2) | 0.0287 (19) | 0.051 (2) | 0.0006 (16) | 0.0279 (19) | −0.0010 (17) |
C25 | 0.039 (2) | 0.052 (3) | 0.037 (2) | 0.0016 (18) | 0.0179 (18) | −0.0107 (18) |
C26 | 0.036 (2) | 0.039 (2) | 0.0285 (17) | 0.0059 (16) | 0.0121 (15) | 0.0006 (16) |
C31 | 0.0243 (16) | 0.0182 (16) | 0.0210 (15) | −0.0047 (12) | 0.0081 (12) | 0.0005 (12) |
C32 | 0.0255 (17) | 0.0249 (17) | 0.0306 (18) | −0.0039 (14) | 0.0113 (14) | −0.0006 (14) |
C33 | 0.0315 (18) | 0.033 (2) | 0.037 (2) | −0.0127 (15) | 0.0159 (15) | −0.0041 (15) |
C34 | 0.046 (2) | 0.0219 (17) | 0.0351 (19) | −0.0119 (16) | 0.0127 (17) | −0.0018 (15) |
C35 | 0.037 (2) | 0.0206 (17) | 0.039 (2) | 0.0009 (15) | 0.0084 (16) | −0.0020 (15) |
C36 | 0.0244 (17) | 0.0232 (17) | 0.0378 (19) | −0.0033 (13) | 0.0090 (15) | −0.0019 (15) |
Geometric parameters (Å, º) top
Cl1—C37 | 1.737 (6) | C10—C31 | 1.544 (4) |
Cl2—C37 | 1.738 (6) | C10—C11 | 1.549 (4) |
Cl3—C37 | 1.738 (6) | C10—C21 | 1.556 (4) |
C37—H37 | 1.0000 | C10—C17 | 1.558 (4) |
Cl1A—C37A | 1.780 (5) | C11—C12 | 1.377 (5) |
Cl2A—C37A | 1.780 (5) | C11—C16 | 1.416 (5) |
Cl3A—C37A | 1.695 (4) | C12—C13 | 1.405 (5) |
C37A—H37A | 1.0002 | C12—H12 | 0.9500 |
Cl1B—C37B | 1.758 (6) | C13—C14 | 1.376 (6) |
Cl2B—C37B | 1.759 (6) | C13—H13 | 0.9500 |
Cl3B—C37B | 1.760 (6) | C14—C15 | 1.379 (6) |
C37B—H37B | 0.9999 | C14—H14 | 0.9500 |
O1—C1 | 1.313 (4) | C15—C16 | 1.391 (5) |
O1—H1 | 0.8400 | C15—H15 | 0.9500 |
O2—C1 | 1.216 (5) | C16—H16 | 0.9500 |
O3—C17 | 1.236 (4) | C21—C26 | 1.379 (5) |
O4—C7 | 1.369 (4) | C21—C22 | 1.410 (5) |
O4—H4 | 0.8400 | C22—C23 | 1.383 (5) |
N1—C17 | 1.339 (4) | C22—H22 | 0.9500 |
N1—C2 | 1.452 (4) | C23—C24 | 1.388 (6) |
N1—H1A | 0.8800 | C23—H23 | 0.9500 |
C1—C2 | 1.511 (5) | C24—C25 | 1.373 (7) |
C2—C3 | 1.542 (5) | C24—H24 | 0.9500 |
C2—H2 | 1.0000 | C25—C26 | 1.394 (6) |
C3—C4 | 1.510 (5) | C25—H25 | 0.9500 |
C3—H3A | 0.9900 | C26—H26 | 0.9500 |
C3—H3B | 0.9900 | C31—C32 | 1.381 (5) |
C4—C9 | 1.387 (5) | C31—C36 | 1.394 (5) |
C4—C5 | 1.392 (5) | C32—C33 | 1.392 (5) |
C5—C6 | 1.385 (6) | C32—H32 | 0.9500 |
C5—H5 | 0.9500 | C33—C34 | 1.387 (6) |
C6—C7 | 1.392 (5) | C33—H33 | 0.9500 |
C6—H6 | 0.9500 | C34—C35 | 1.392 (6) |
C7—C8 | 1.390 (5) | C34—H34 | 0.9500 |
C8—C9 | 1.378 (5) | C35—C36 | 1.381 (5) |
C8—H8 | 0.9500 | C35—H35 | 0.9500 |
C9—H9 | 0.9500 | C36—H36 | 0.9500 |
| | | |
Cl1—C37—Cl2 | 111.2 | C11—C10—C17 | 111.0 (2) |
Cl1—C37—Cl3 | 111.2 | C21—C10—C17 | 108.3 (3) |
Cl2—C37—Cl3 | 111.2 | C12—C11—C16 | 117.9 (3) |
Cl1—C37—H37 | 107.7 | C12—C11—C10 | 123.1 (3) |
Cl2—C37—H37 | 107.7 | C16—C11—C10 | 118.9 (3) |
Cl3—C37—H37 | 107.7 | C11—C12—C13 | 121.0 (3) |
Cl3A—C37A—Cl1A | 112.3 | C11—C12—H12 | 119.5 |
Cl3A—C37A—Cl2A | 112.3 | C13—C12—H12 | 119.5 |
Cl1A—C37A—Cl2A | 108.4 | C14—C13—C12 | 120.6 (4) |
Cl3A—C37A—H37A | 107.9 | C14—C13—H13 | 119.7 |
Cl1A—C37A—H37A | 107.9 | C12—C13—H13 | 119.7 |
Cl2A—C37A—H37A | 107.9 | C13—C14—C15 | 119.3 (3) |
Cl1B—C37B—Cl2B | 111.2 | C13—C14—H14 | 120.3 |
Cl1B—C37B—Cl3B | 111.2 | C15—C14—H14 | 120.3 |
Cl2B—C37B—Cl3B | 111.2 | C14—C15—C16 | 120.7 (3) |
Cl1B—C37B—H37B | 107.7 | C14—C15—H15 | 119.6 |
Cl2B—C37B—H37B | 107.7 | C16—C15—H15 | 119.6 |
Cl3B—C37B—H37B | 107.7 | C15—C16—C11 | 120.5 (3) |
C1—O1—H1 | 109.5 | C15—C16—H16 | 119.8 |
C7—O4—H4 | 109.5 | C11—C16—H16 | 119.8 |
C17—N1—C2 | 123.0 (3) | O3—C17—N1 | 121.8 (3) |
C17—N1—H1A | 118.5 | O3—C17—C10 | 119.8 (3) |
C2—N1—H1A | 118.5 | N1—C17—C10 | 118.4 (3) |
O2—C1—O1 | 124.3 (3) | C26—C21—C22 | 117.7 (3) |
O2—C1—C2 | 123.7 (3) | C26—C21—C10 | 124.0 (3) |
O1—C1—C2 | 112.0 (3) | C22—C21—C10 | 118.3 (3) |
N1—C2—C1 | 109.4 (3) | C23—C22—C21 | 120.6 (3) |
N1—C2—C3 | 111.1 (3) | C23—C22—H22 | 119.7 |
C1—C2—C3 | 109.8 (3) | C21—C22—H22 | 119.7 |
N1—C2—H2 | 108.8 | C22—C23—C24 | 120.6 (4) |
C1—C2—H2 | 108.8 | C22—C23—H23 | 119.7 |
C3—C2—H2 | 108.8 | C24—C23—H23 | 119.7 |
C4—C3—C2 | 110.7 (3) | C25—C24—C23 | 119.2 (4) |
C4—C3—H3A | 109.5 | C25—C24—H24 | 120.4 |
C2—C3—H3A | 109.5 | C23—C24—H24 | 120.4 |
C4—C3—H3B | 109.5 | C24—C25—C26 | 120.4 (4) |
C2—C3—H3B | 109.5 | C24—C25—H25 | 119.8 |
H3A—C3—H3B | 108.1 | C26—C25—H25 | 119.8 |
C9—C4—C5 | 117.8 (3) | C21—C26—C25 | 121.4 (4) |
C9—C4—C3 | 120.8 (3) | C21—C26—H26 | 119.3 |
C5—C4—C3 | 121.4 (3) | C25—C26—H26 | 119.3 |
C6—C5—C4 | 121.3 (3) | C32—C31—C36 | 118.6 (3) |
C6—C5—H5 | 119.4 | C32—C31—C10 | 122.6 (3) |
C4—C5—H5 | 119.4 | C36—C31—C10 | 118.7 (3) |
C5—C6—C7 | 119.6 (3) | C31—C32—C33 | 120.3 (3) |
C5—C6—H6 | 120.2 | C31—C32—H32 | 119.9 |
C7—C6—H6 | 120.2 | C33—C32—H32 | 119.9 |
O4—C7—C8 | 122.5 (3) | C34—C33—C32 | 120.9 (3) |
O4—C7—C6 | 117.6 (3) | C34—C33—H33 | 119.5 |
C8—C7—C6 | 119.9 (3) | C32—C33—H33 | 119.5 |
C9—C8—C7 | 119.4 (3) | C33—C34—C35 | 118.9 (3) |
C9—C8—H8 | 120.3 | C33—C34—H34 | 120.5 |
C7—C8—H8 | 120.3 | C35—C34—H34 | 120.5 |
C8—C9—C4 | 122.0 (3) | C36—C35—C34 | 119.9 (4) |
C8—C9—H9 | 119.0 | C36—C35—H35 | 120.0 |
C4—C9—H9 | 119.0 | C34—C35—H35 | 120.0 |
C31—C10—C11 | 111.5 (3) | C35—C36—C31 | 121.3 (3) |
C31—C10—C21 | 112.5 (2) | C35—C36—H36 | 119.3 |
C11—C10—C21 | 108.9 (3) | C31—C36—H36 | 119.3 |
C31—C10—C17 | 104.6 (2) | | |
| | | |
C17—N1—C2—C1 | −111.7 (3) | C2—N1—C17—C10 | 178.5 (3) |
C17—N1—C2—C3 | 126.9 (3) | C31—C10—C17—O3 | −50.0 (4) |
O2—C1—C2—N1 | −20.9 (4) | C11—C10—C17—O3 | −170.3 (3) |
O1—C1—C2—N1 | 160.2 (3) | C21—C10—C17—O3 | 70.2 (3) |
O2—C1—C2—C3 | 101.3 (4) | C31—C10—C17—N1 | 129.7 (3) |
O1—C1—C2—C3 | −77.7 (3) | C11—C10—C17—N1 | 9.3 (4) |
N1—C2—C3—C4 | −62.2 (4) | C21—C10—C17—N1 | −110.1 (3) |
C1—C2—C3—C4 | 176.7 (3) | C31—C10—C21—C26 | 92.5 (4) |
C2—C3—C4—C9 | −79.0 (4) | C11—C10—C21—C26 | −143.4 (3) |
C2—C3—C4—C5 | 98.3 (4) | C17—C10—C21—C26 | −22.6 (4) |
C9—C4—C5—C6 | 1.9 (5) | C31—C10—C21—C22 | −86.2 (4) |
C3—C4—C5—C6 | −175.5 (3) | C11—C10—C21—C22 | 37.9 (4) |
C4—C5—C6—C7 | −0.5 (6) | C17—C10—C21—C22 | 158.6 (3) |
C5—C6—C7—O4 | 178.6 (3) | C26—C21—C22—C23 | 2.8 (5) |
C5—C6—C7—C8 | −1.5 (5) | C10—C21—C22—C23 | −178.4 (3) |
O4—C7—C8—C9 | −178.1 (3) | C21—C22—C23—C24 | 0.5 (6) |
C6—C7—C8—C9 | 2.0 (5) | C22—C23—C24—C25 | −2.7 (6) |
C7—C8—C9—C4 | −0.5 (5) | C23—C24—C25—C26 | 1.7 (7) |
C5—C4—C9—C8 | −1.4 (5) | C22—C21—C26—C25 | −3.8 (6) |
C3—C4—C9—C8 | 176.0 (3) | C10—C21—C26—C25 | 177.4 (4) |
C31—C10—C11—C12 | −8.2 (4) | C24—C25—C26—C21 | 1.6 (7) |
C21—C10—C11—C12 | −132.9 (3) | C11—C10—C31—C32 | −99.8 (4) |
C17—C10—C11—C12 | 108.0 (3) | C21—C10—C31—C32 | 22.9 (4) |
C31—C10—C11—C16 | 173.2 (3) | C17—C10—C31—C32 | 140.2 (3) |
C21—C10—C11—C16 | 48.5 (4) | C11—C10—C31—C36 | 78.0 (4) |
C17—C10—C11—C16 | −70.6 (4) | C21—C10—C31—C36 | −159.3 (3) |
C16—C11—C12—C13 | 0.4 (5) | C17—C10—C31—C36 | −42.0 (4) |
C10—C11—C12—C13 | −178.2 (3) | C36—C31—C32—C33 | 0.6 (5) |
C11—C12—C13—C14 | 1.0 (6) | C10—C31—C32—C33 | 178.4 (3) |
C12—C13—C14—C15 | −0.9 (6) | C31—C32—C33—C34 | 0.3 (6) |
C13—C14—C15—C16 | −0.5 (6) | C32—C33—C34—C35 | −0.6 (6) |
C14—C15—C16—C11 | 1.8 (5) | C33—C34—C35—C36 | 0.2 (6) |
C12—C11—C16—C15 | −1.8 (5) | C34—C35—C36—C31 | 0.7 (6) |
C10—C11—C16—C15 | 176.9 (3) | C32—C31—C36—C35 | −1.1 (5) |
C2—N1—C17—O3 | −1.9 (5) | C10—C31—C36—C35 | −179.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O3i | 0.95 | 2.53 | 3.427 (4) | 157 |
C3—H3A···Cl3ii | 0.99 | 2.88 | 3.85 (5) | 165 |
C37—H37···O4 | 1.00 | 2.32 | 3.165 (7) | 142 |
C37A—H37A···O4 | 1.00 | 2.20 | 3.183 (6) | 167 |
C37B—H37B···O4 | 1.00 | 2.06 | 3.055 (8) | 172 |
O1—H1···O3iii | 0.84 | 1.81 | 2.642 (4) | 174 |
O4—H4···O2iv | 0.84 | 1.93 | 2.762 (4) | 174 |
C26—H26···O3 | 0.95 | 2.27 | 2.946 (5) | 127 |
Symmetry codes: (i) −x+2, y−1/2, −z+2; (ii) x, y+1, z; (iii) −x+2, y+1/2, −z+2; (iv) x, y−1, z. |
N-Triphenylacetyl-
L-tyrosine dichloromethane monosolvate (II)
top
Crystal data top
C29H25NO4·CH2Cl2 | F(000) = 560 |
Mr = 536.42 | Dx = 1.306 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 10.04475 (13) Å | Cell parameters from 12253 reflections |
b = 9.82563 (12) Å | θ = 3.2–75.4° |
c = 14.59465 (18) Å | µ = 2.43 mm−1 |
β = 108.7422 (13)° | T = 130 K |
V = 1364.05 (3) Å3 | Needle, colourless |
Z = 2 | 0.30 × 0.06 × 0.03 mm |
Data collection top
Rigaku SuperNova Single Source diffractometer with an Atlas detector | 5550 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5259 reflections with I > 2σ(I) |
Detector resolution: 10.5357 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 75.6°, θmin = 3.2° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2021) | h = −12→11 |
Tmin = 0.709, Tmax = 1.000 | k = −12→12 |
20920 measured reflections | l = −17→18 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2497P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.42 e Å−3 |
5550 reflections | Δρmin = −0.49 e Å−3 |
336 parameters | Absolute structure: Flack x determined using 2293 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.009 (9) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The diffraction data for all monocrystals were collected at 130 K
with an Oxford Diffraction SuperNova diffractometer using Cu Kα radiation
(λ = 1.54184 Å). The intensity data were collected and processed with
the use of CrysAlis PRO software (1.171.40.67a). The structures were
solved by
direct methods with the program SHELXT2018 (Sheldrick, 2015b) and
refined by full-matrix least-squares method on F2 with SHELXL2018
(Sheldrick, 2015a). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 1.13556 (10) | 0.08291 (17) | 0.54019 (7) | 0.0754 (4) | |
Cl2 | 0.84252 (11) | 0.15911 (11) | 0.45184 (6) | 0.0586 (3) | |
C41 | 0.9600 (4) | 0.0360 (4) | 0.5188 (3) | 0.0474 (8) | |
H41A | 0.943632 | 0.022081 | 0.581518 | 0.057* | |
H41B | 0.941735 | −0.051474 | 0.483243 | 0.057* | |
O1 | 1.15801 (19) | 0.8586 (2) | 1.01800 (13) | 0.0284 (4) | |
H1 | 1.186840 | 0.938099 | 1.033941 | 0.043* | |
O2 | 0.9936 (2) | 0.96528 (19) | 0.89904 (15) | 0.0332 (4) | |
O3 | 0.9396 (2) | 0.1219 (2) | 0.73314 (14) | 0.0364 (5) | |
H3 | 0.952053 | 0.072273 | 0.782044 | 0.055* | |
O4 | 0.76577 (18) | 0.61269 (18) | 0.93338 (12) | 0.0257 (4) | |
N1 | 0.8592 (2) | 0.7258 (2) | 0.83509 (14) | 0.0217 (4) | |
H1A | 0.843585 | 0.765140 | 0.778439 | 0.026* | |
C1 | 1.0496 (3) | 0.8623 (3) | 0.93869 (17) | 0.0236 (5) | |
C2 | 1.0026 (3) | 0.7203 (2) | 0.90046 (18) | 0.0227 (5) | |
H2 | 1.006458 | 0.659202 | 0.956024 | 0.027* | |
C3 | 1.1028 (3) | 0.6647 (3) | 0.84801 (18) | 0.0251 (5) | |
H3A | 1.095903 | 0.722169 | 0.790950 | 0.030* | |
H3B | 1.200955 | 0.668870 | 0.892152 | 0.030* | |
C4 | 1.0664 (3) | 0.5200 (3) | 0.81597 (18) | 0.0245 (5) | |
C5 | 1.1076 (3) | 0.4138 (3) | 0.88251 (19) | 0.0257 (5) | |
H5 | 1.163987 | 0.433217 | 0.947078 | 0.031* | |
C6 | 1.0678 (3) | 0.2802 (3) | 0.85641 (19) | 0.0270 (5) | |
H6 | 1.097140 | 0.209026 | 0.902608 | 0.032* | |
C7 | 0.9847 (3) | 0.2516 (3) | 0.76208 (19) | 0.0274 (5) | |
C8 | 0.9453 (3) | 0.3547 (3) | 0.69411 (18) | 0.0289 (5) | |
H8 | 0.890933 | 0.334624 | 0.629193 | 0.035* | |
C9 | 0.9859 (3) | 0.4883 (3) | 0.72144 (19) | 0.0270 (5) | |
H9 | 0.958162 | 0.558968 | 0.674713 | 0.032* | |
C10 | 0.6012 (2) | 0.6880 (2) | 0.78117 (17) | 0.0212 (5) | |
C11 | 0.6083 (2) | 0.7486 (3) | 0.68512 (17) | 0.0221 (5) | |
C12 | 0.6453 (3) | 0.8859 (3) | 0.68206 (18) | 0.0251 (5) | |
H12 | 0.663110 | 0.940556 | 0.738430 | 0.030* | |
C13 | 0.6564 (3) | 0.9432 (3) | 0.5973 (2) | 0.0288 (5) | |
H13 | 0.683813 | 1.035645 | 0.596864 | 0.035* | |
C14 | 0.6277 (3) | 0.8661 (3) | 0.51419 (19) | 0.0301 (5) | |
H14 | 0.634549 | 0.905283 | 0.456351 | 0.036* | |
C15 | 0.5886 (3) | 0.7304 (3) | 0.51593 (19) | 0.0305 (6) | |
H15 | 0.567754 | 0.676950 | 0.458790 | 0.037* | |
C16 | 0.5799 (3) | 0.6726 (3) | 0.60071 (18) | 0.0263 (5) | |
H16 | 0.554042 | 0.579625 | 0.600972 | 0.032* | |
C17 | 0.7502 (2) | 0.6744 (2) | 0.85630 (17) | 0.0206 (4) | |
C21 | 0.5117 (3) | 0.7848 (2) | 0.82243 (18) | 0.0227 (5) | |
C22 | 0.3945 (3) | 0.8478 (3) | 0.75796 (18) | 0.0256 (5) | |
H22 | 0.369741 | 0.828556 | 0.690768 | 0.031* | |
C23 | 0.3129 (3) | 0.9389 (3) | 0.7907 (2) | 0.0297 (6) | |
H23 | 0.233011 | 0.980409 | 0.745807 | 0.036* | |
C24 | 0.3479 (3) | 0.9688 (3) | 0.8881 (2) | 0.0328 (6) | |
H24 | 0.294631 | 1.033145 | 0.910305 | 0.039* | |
C25 | 0.4617 (3) | 0.9037 (3) | 0.9527 (2) | 0.0378 (7) | |
H25 | 0.485185 | 0.922081 | 1.019981 | 0.045* | |
C26 | 0.5421 (3) | 0.8118 (3) | 0.92074 (19) | 0.0309 (6) | |
H26 | 0.618712 | 0.766876 | 0.966426 | 0.037* | |
C31 | 0.5431 (3) | 0.5412 (2) | 0.76796 (17) | 0.0225 (5) | |
C32 | 0.4068 (3) | 0.5095 (3) | 0.76339 (18) | 0.0262 (5) | |
H32 | 0.344653 | 0.579787 | 0.768608 | 0.031* | |
C33 | 0.3602 (3) | 0.3744 (3) | 0.7511 (2) | 0.0313 (6) | |
H33 | 0.266319 | 0.353784 | 0.747567 | 0.038* | |
C34 | 0.4494 (3) | 0.2708 (3) | 0.7441 (2) | 0.0333 (6) | |
H34 | 0.417461 | 0.179169 | 0.736507 | 0.040* | |
C35 | 0.5863 (3) | 0.3017 (3) | 0.7482 (2) | 0.0308 (6) | |
H35 | 0.648332 | 0.231186 | 0.743270 | 0.037* | |
C36 | 0.6320 (3) | 0.4359 (3) | 0.7594 (2) | 0.0274 (5) | |
H36 | 0.725309 | 0.456495 | 0.761323 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0413 (5) | 0.1376 (11) | 0.0424 (5) | −0.0195 (6) | 0.0067 (4) | 0.0034 (6) |
Cl2 | 0.0611 (5) | 0.0630 (6) | 0.0427 (4) | 0.0072 (4) | 0.0042 (4) | −0.0048 (4) |
C41 | 0.0401 (17) | 0.062 (2) | 0.0408 (17) | −0.0040 (16) | 0.0137 (14) | −0.0014 (16) |
O1 | 0.0273 (9) | 0.0271 (9) | 0.0265 (8) | −0.0043 (8) | 0.0026 (7) | −0.0057 (8) |
O2 | 0.0349 (11) | 0.0216 (9) | 0.0371 (10) | −0.0009 (8) | 0.0033 (8) | 0.0012 (8) |
O3 | 0.0504 (12) | 0.0242 (9) | 0.0324 (10) | −0.0087 (9) | 0.0105 (9) | −0.0056 (8) |
O4 | 0.0242 (8) | 0.0276 (9) | 0.0238 (8) | 0.0006 (7) | 0.0056 (7) | 0.0065 (7) |
N1 | 0.0209 (10) | 0.0222 (9) | 0.0203 (9) | −0.0027 (8) | 0.0044 (8) | 0.0031 (8) |
C1 | 0.0218 (11) | 0.0243 (11) | 0.0251 (11) | −0.0007 (10) | 0.0083 (9) | −0.0003 (10) |
C2 | 0.0210 (11) | 0.0221 (11) | 0.0228 (11) | −0.0021 (9) | 0.0042 (9) | 0.0000 (9) |
C3 | 0.0226 (12) | 0.0242 (12) | 0.0289 (12) | −0.0046 (9) | 0.0087 (10) | −0.0016 (10) |
C4 | 0.0237 (11) | 0.0234 (11) | 0.0275 (12) | −0.0013 (10) | 0.0100 (10) | −0.0025 (10) |
C5 | 0.0243 (12) | 0.0266 (12) | 0.0248 (12) | −0.0006 (9) | 0.0060 (10) | −0.0022 (10) |
C6 | 0.0301 (13) | 0.0244 (12) | 0.0272 (12) | 0.0007 (10) | 0.0100 (10) | −0.0001 (10) |
C7 | 0.0295 (13) | 0.0245 (12) | 0.0292 (12) | −0.0026 (10) | 0.0108 (10) | −0.0049 (10) |
C8 | 0.0311 (13) | 0.0307 (13) | 0.0231 (11) | −0.0036 (11) | 0.0063 (10) | −0.0046 (10) |
C9 | 0.0299 (13) | 0.0251 (13) | 0.0258 (12) | −0.0006 (10) | 0.0087 (10) | 0.0018 (10) |
C10 | 0.0203 (11) | 0.0202 (11) | 0.0217 (11) | −0.0013 (9) | 0.0048 (9) | −0.0002 (9) |
C11 | 0.0185 (11) | 0.0243 (12) | 0.0217 (11) | 0.0010 (9) | 0.0039 (9) | 0.0021 (9) |
C12 | 0.0249 (12) | 0.0236 (12) | 0.0249 (12) | −0.0006 (9) | 0.0052 (9) | 0.0015 (10) |
C13 | 0.0293 (13) | 0.0248 (12) | 0.0310 (13) | 0.0007 (10) | 0.0079 (11) | 0.0072 (10) |
C14 | 0.0304 (13) | 0.0354 (14) | 0.0254 (12) | 0.0014 (11) | 0.0101 (10) | 0.0090 (11) |
C15 | 0.0330 (14) | 0.0361 (14) | 0.0222 (11) | −0.0029 (11) | 0.0086 (10) | −0.0018 (11) |
C16 | 0.0276 (12) | 0.0255 (12) | 0.0248 (12) | −0.0021 (10) | 0.0069 (10) | 0.0012 (10) |
C17 | 0.0226 (11) | 0.0173 (10) | 0.0220 (10) | 0.0007 (9) | 0.0072 (9) | −0.0013 (9) |
C21 | 0.0221 (11) | 0.0206 (11) | 0.0258 (11) | −0.0030 (9) | 0.0083 (9) | 0.0003 (9) |
C22 | 0.0231 (11) | 0.0267 (12) | 0.0259 (11) | −0.0018 (10) | 0.0063 (9) | 0.0000 (10) |
C23 | 0.0256 (13) | 0.0253 (13) | 0.0391 (14) | 0.0027 (10) | 0.0114 (11) | 0.0071 (11) |
C24 | 0.0305 (14) | 0.0309 (14) | 0.0435 (16) | 0.0002 (11) | 0.0211 (12) | −0.0040 (12) |
C25 | 0.0392 (16) | 0.0434 (16) | 0.0320 (14) | 0.0022 (13) | 0.0133 (12) | −0.0064 (12) |
C26 | 0.0278 (13) | 0.0377 (15) | 0.0264 (12) | 0.0039 (11) | 0.0075 (10) | −0.0010 (11) |
C31 | 0.0253 (12) | 0.0221 (12) | 0.0195 (10) | −0.0030 (9) | 0.0063 (9) | −0.0002 (9) |
C32 | 0.0254 (12) | 0.0275 (12) | 0.0271 (12) | −0.0030 (10) | 0.0102 (10) | −0.0009 (10) |
C33 | 0.0314 (13) | 0.0316 (14) | 0.0337 (13) | −0.0110 (12) | 0.0142 (11) | −0.0044 (11) |
C34 | 0.0433 (16) | 0.0252 (12) | 0.0316 (13) | −0.0112 (11) | 0.0121 (12) | −0.0044 (11) |
C35 | 0.0359 (14) | 0.0242 (13) | 0.0318 (13) | 0.0018 (11) | 0.0100 (11) | −0.0019 (10) |
C36 | 0.0257 (13) | 0.0245 (12) | 0.0310 (13) | −0.0020 (10) | 0.0077 (10) | −0.0011 (10) |
Geometric parameters (Å, º) top
Cl1—C41 | 1.751 (4) | C11—C16 | 1.390 (4) |
Cl2—C41 | 1.752 (4) | C11—C12 | 1.404 (3) |
C41—H41A | 0.9900 | C12—C13 | 1.395 (4) |
C41—H41B | 0.9900 | C12—H12 | 0.9500 |
O1—C1 | 1.310 (3) | C13—C14 | 1.380 (4) |
O1—H1 | 0.8400 | C13—H13 | 0.9500 |
O2—C1 | 1.211 (3) | C14—C15 | 1.393 (4) |
O3—C7 | 1.372 (3) | C14—H14 | 0.9500 |
O3—H3 | 0.8400 | C15—C16 | 1.389 (4) |
O4—C17 | 1.243 (3) | C15—H15 | 0.9500 |
N1—C17 | 1.329 (3) | C16—H16 | 0.9500 |
N1—C2 | 1.451 (3) | C21—C26 | 1.393 (4) |
N1—H1A | 0.8800 | C21—C22 | 1.394 (3) |
C1—C2 | 1.520 (3) | C22—C23 | 1.397 (4) |
C2—C3 | 1.547 (4) | C22—H22 | 0.9500 |
C2—H2 | 1.0000 | C23—C24 | 1.382 (4) |
C3—C4 | 1.505 (4) | C23—H23 | 0.9500 |
C3—H3A | 0.9900 | C24—C25 | 1.383 (4) |
C3—H3B | 0.9900 | C24—H24 | 0.9500 |
C4—C9 | 1.392 (4) | C25—C26 | 1.388 (4) |
C4—C5 | 1.395 (4) | C25—H25 | 0.9500 |
C5—C6 | 1.389 (4) | C26—H26 | 0.9500 |
C5—H5 | 0.9500 | C31—C32 | 1.385 (4) |
C6—C7 | 1.390 (4) | C31—C36 | 1.399 (4) |
C6—H6 | 0.9500 | C32—C33 | 1.400 (4) |
C7—C8 | 1.384 (4) | C32—H32 | 0.9500 |
C8—C9 | 1.394 (4) | C33—C34 | 1.382 (4) |
C8—H8 | 0.9500 | C33—H33 | 0.9500 |
C9—H9 | 0.9500 | C34—C35 | 1.390 (4) |
C10—C31 | 1.544 (3) | C34—H34 | 0.9500 |
C10—C11 | 1.546 (3) | C35—C36 | 1.389 (4) |
C10—C17 | 1.551 (3) | C35—H35 | 0.9500 |
C10—C21 | 1.557 (3) | C36—H36 | 0.9500 |
| | | |
Cl1—C41—Cl2 | 112.1 (2) | C13—C12—H12 | 119.6 |
Cl1—C41—H41A | 109.2 | C11—C12—H12 | 119.6 |
Cl2—C41—H41A | 109.2 | C14—C13—C12 | 120.3 (2) |
Cl1—C41—H41B | 109.2 | C14—C13—H13 | 119.8 |
Cl2—C41—H41B | 109.2 | C12—C13—H13 | 119.8 |
H41A—C41—H41B | 107.9 | C13—C14—C15 | 119.3 (2) |
C1—O1—H1 | 109.5 | C13—C14—H14 | 120.3 |
C7—O3—H3 | 109.5 | C15—C14—H14 | 120.3 |
C17—N1—C2 | 123.4 (2) | C16—C15—C14 | 120.4 (2) |
C17—N1—H1A | 118.3 | C16—C15—H15 | 119.8 |
C2—N1—H1A | 118.3 | C14—C15—H15 | 119.8 |
O2—C1—O1 | 124.9 (2) | C15—C16—C11 | 121.1 (2) |
O2—C1—C2 | 123.3 (2) | C15—C16—H16 | 119.5 |
O1—C1—C2 | 111.7 (2) | C11—C16—H16 | 119.5 |
N1—C2—C1 | 109.5 (2) | O4—C17—N1 | 121.5 (2) |
N1—C2—C3 | 110.7 (2) | O4—C17—C10 | 119.6 (2) |
C1—C2—C3 | 109.3 (2) | N1—C17—C10 | 118.9 (2) |
N1—C2—H2 | 109.1 | C26—C21—C22 | 117.9 (2) |
C1—C2—H2 | 109.1 | C26—C21—C10 | 123.5 (2) |
C3—C2—H2 | 109.1 | C22—C21—C10 | 118.5 (2) |
C4—C3—C2 | 110.8 (2) | C21—C22—C23 | 121.0 (2) |
C4—C3—H3A | 109.5 | C21—C22—H22 | 119.5 |
C2—C3—H3A | 109.5 | C23—C22—H22 | 119.5 |
C4—C3—H3B | 109.5 | C24—C23—C22 | 120.3 (3) |
C2—C3—H3B | 109.5 | C24—C23—H23 | 119.8 |
H3A—C3—H3B | 108.1 | C22—C23—H23 | 119.8 |
C9—C4—C5 | 118.1 (2) | C23—C24—C25 | 119.0 (3) |
C9—C4—C3 | 121.7 (2) | C23—C24—H24 | 120.5 |
C5—C4—C3 | 120.2 (2) | C25—C24—H24 | 120.5 |
C6—C5—C4 | 121.4 (2) | C24—C25—C26 | 120.9 (3) |
C6—C5—H5 | 119.3 | C24—C25—H25 | 119.5 |
C4—C5—H5 | 119.3 | C26—C25—H25 | 119.5 |
C5—C6—C7 | 119.4 (2) | C25—C26—C21 | 120.8 (3) |
C5—C6—H6 | 120.3 | C25—C26—H26 | 119.6 |
C7—C6—H6 | 120.3 | C21—C26—H26 | 119.6 |
O3—C7—C8 | 118.0 (2) | C32—C31—C36 | 118.6 (2) |
O3—C7—C6 | 121.8 (2) | C32—C31—C10 | 123.0 (2) |
C8—C7—C6 | 120.3 (2) | C36—C31—C10 | 118.4 (2) |
C7—C8—C9 | 119.6 (2) | C31—C32—C33 | 120.3 (2) |
C7—C8—H8 | 120.2 | C31—C32—H32 | 119.9 |
C9—C8—H8 | 120.2 | C33—C32—H32 | 119.9 |
C4—C9—C8 | 121.2 (2) | C34—C33—C32 | 120.7 (3) |
C4—C9—H9 | 119.4 | C34—C33—H33 | 119.6 |
C8—C9—H9 | 119.4 | C32—C33—H33 | 119.6 |
C31—C10—C11 | 111.86 (19) | C33—C34—C35 | 119.4 (3) |
C31—C10—C17 | 104.37 (19) | C33—C34—H34 | 120.3 |
C11—C10—C17 | 111.07 (19) | C35—C34—H34 | 120.3 |
C31—C10—C21 | 112.13 (19) | C36—C35—C34 | 119.9 (3) |
C11—C10—C21 | 108.40 (19) | C36—C35—H35 | 120.1 |
C17—C10—C21 | 108.97 (19) | C34—C35—H35 | 120.1 |
C16—C11—C12 | 118.0 (2) | C35—C36—C31 | 121.1 (3) |
C16—C11—C10 | 122.7 (2) | C35—C36—H36 | 119.5 |
C12—C11—C10 | 119.3 (2) | C31—C36—H36 | 119.5 |
C13—C12—C11 | 120.9 (2) | | |
| | | |
C17—N1—C2—C1 | −109.4 (3) | C2—N1—C17—C10 | 179.2 (2) |
C17—N1—C2—C3 | 130.0 (2) | C31—C10—C17—O4 | −50.8 (3) |
O2—C1—C2—N1 | −20.3 (3) | C11—C10—C17—O4 | −171.5 (2) |
O1—C1—C2—N1 | 160.6 (2) | C21—C10—C17—O4 | 69.2 (3) |
O2—C1—C2—C3 | 101.2 (3) | C31—C10—C17—N1 | 127.1 (2) |
O1—C1—C2—C3 | −77.9 (3) | C11—C10—C17—N1 | 6.4 (3) |
N1—C2—C3—C4 | −63.8 (3) | C21—C10—C17—N1 | −112.9 (2) |
C1—C2—C3—C4 | 175.5 (2) | C31—C10—C21—C26 | 93.5 (3) |
C2—C3—C4—C9 | 98.6 (3) | C11—C10—C21—C26 | −142.5 (2) |
C2—C3—C4—C5 | −78.3 (3) | C17—C10—C21—C26 | −21.5 (3) |
C9—C4—C5—C6 | −1.2 (4) | C31—C10—C21—C22 | −86.3 (3) |
C3—C4—C5—C6 | 175.9 (2) | C11—C10—C21—C22 | 37.7 (3) |
C4—C5—C6—C7 | −0.3 (4) | C17—C10—C21—C22 | 158.7 (2) |
C5—C6—C7—O3 | −178.4 (3) | C26—C21—C22—C23 | 2.2 (4) |
C5—C6—C7—C8 | 1.8 (4) | C10—C21—C22—C23 | −178.0 (2) |
O3—C7—C8—C9 | 178.3 (3) | C21—C22—C23—C24 | 0.4 (4) |
C6—C7—C8—C9 | −1.9 (4) | C22—C23—C24—C25 | −2.3 (4) |
C5—C4—C9—C8 | 1.1 (4) | C23—C24—C25—C26 | 1.5 (5) |
C3—C4—C9—C8 | −175.9 (3) | C24—C25—C26—C21 | 1.2 (5) |
C7—C8—C9—C4 | 0.4 (4) | C22—C21—C26—C25 | −3.0 (4) |
C31—C10—C11—C16 | −6.6 (3) | C10—C21—C26—C25 | 177.2 (3) |
C17—C10—C11—C16 | 109.6 (3) | C11—C10—C31—C32 | −102.8 (3) |
C21—C10—C11—C16 | −130.7 (2) | C17—C10—C31—C32 | 137.0 (2) |
C31—C10—C11—C12 | 173.7 (2) | C21—C10—C31—C32 | 19.2 (3) |
C17—C10—C11—C12 | −70.2 (3) | C11—C10—C31—C36 | 76.6 (3) |
C21—C10—C11—C12 | 49.5 (3) | C17—C10—C31—C36 | −43.6 (3) |
C16—C11—C12—C13 | −1.5 (4) | C21—C10—C31—C36 | −161.4 (2) |
C10—C11—C12—C13 | 178.3 (2) | C36—C31—C32—C33 | 0.4 (4) |
C11—C12—C13—C14 | 1.5 (4) | C10—C31—C32—C33 | 179.9 (2) |
C12—C13—C14—C15 | −0.5 (4) | C31—C32—C33—C34 | 0.5 (4) |
C13—C14—C15—C16 | −0.6 (4) | C32—C33—C34—C35 | −0.7 (4) |
C14—C15—C16—C11 | 0.7 (4) | C33—C34—C35—C36 | 0.1 (4) |
C12—C11—C16—C15 | 0.4 (4) | C34—C35—C36—C31 | 0.8 (4) |
C10—C11—C16—C15 | −179.4 (2) | C32—C31—C36—C35 | −1.1 (4) |
C2—N1—C17—O4 | −2.9 (4) | C10—C31—C36—C35 | 179.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.84 | 1.80 | 2.641 (3) | 175 |
O3—H3···O2ii | 0.84 | 1.93 | 2.772 (3) | 176 |
C26—H26···O4 | 0.95 | 2.27 | 2.940 (3) | 127 |
C6—H6···O2ii | 0.95 | 2.60 | 3.288 (3) | 129 |
C6—H6···O4iii | 0.95 | 2.53 | 3.409 (3) | 154 |
Symmetry codes: (i) −x+2, y+1/2, −z+2; (ii) x, y−1, z; (iii) −x+2, y−1/2, −z+2. |
N-Triphenylacetyl-
L-tyrosine chloroform monosolvate (III)
top
Crystal data top
C29H25NO4·CHCl3 | Dx = 1.268 Mg m−3 |
Mr = 570.87 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P21212 | Cell parameters from 16633 reflections |
a = 9.27898 (12) Å | θ = 2.7–75.8° |
b = 32.3574 (4) Å | µ = 3.05 mm−1 |
c = 9.96336 (12) Å | T = 130 K |
V = 2991.44 (6) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.02 × 0.01 mm |
F(000) = 1184 | |
Data collection top
Rigaku SuperNova Single Source diffractometer with an Atlas detector | 6241 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5987 reflections with I > 2σ(I) |
Detector resolution: 10.5384 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 76.4°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | h = −11→11 |
Tmin = 0.713, Tmax = 1.000 | k = −39→40 |
29945 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0408P)2 + 0.7639P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.21 e Å−3 |
6241 reflections | Δρmin = −0.27 e Å−3 |
344 parameters | Absolute structure: Flack x determined using 2454 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.034 (6) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The diffraction data for all monocrystals were collected at 130 K
with an Oxford Diffraction SuperNova diffractometer using Cu Kα radiation
(λ = 1.54184 Å). The intensity data were collected and processed with
the use of CrysAlis PRO software (1.171.40.67a). The structures were
solved by
direct methods with the program SHELXT2018 (Sheldrick, 2015b) and
refined by full-matrix least-squares method on F2 with SHELXL2018
(Sheldrick, 2015a). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.9127 (3) | 0.46789 (7) | −0.0720 (2) | 0.0530 (6) | |
H1 | 0.979664 | 0.484917 | −0.059360 | 0.079* | 0.5 |
O2 | 0.8941 (2) | 0.47305 (6) | 0.15019 (19) | 0.0377 (4) | |
H2 | 0.963379 | 0.489433 | 0.139264 | 0.057* | 0.5 |
O3 | 0.9123 (2) | 0.37124 (7) | 0.1455 (2) | 0.0460 (5) | |
O4 | 0.10401 (18) | 0.35096 (6) | −0.03917 (18) | 0.0386 (4) | |
H4 | 0.041660 | 0.358343 | 0.017050 | 0.058* | |
N1 | 0.7082 (2) | 0.40642 (6) | 0.15963 (19) | 0.0261 (4) | |
H1A | 0.630980 | 0.412678 | 0.206635 | 0.031* | |
C1 | 0.8589 (2) | 0.45775 (7) | 0.0390 (2) | 0.0285 (4) | |
C2 | 0.7342 (2) | 0.42723 (7) | 0.0320 (2) | 0.0271 (4) | |
H2A | 0.755494 | 0.406033 | −0.038355 | 0.033* | |
C3 | 0.6009 (3) | 0.45209 (8) | −0.0103 (3) | 0.0349 (5) | |
H3A | 0.584934 | 0.474593 | 0.055399 | 0.042* | |
H3B | 0.619383 | 0.464963 | −0.098751 | 0.042* | |
C4 | 0.4661 (2) | 0.42614 (7) | −0.0193 (2) | 0.0306 (5) | |
C5 | 0.3537 (3) | 0.43154 (7) | 0.0714 (3) | 0.0331 (5) | |
H5 | 0.361085 | 0.452285 | 0.138521 | 0.040* | |
C6 | 0.2312 (2) | 0.40720 (7) | 0.0654 (2) | 0.0314 (5) | |
H6 | 0.155002 | 0.411452 | 0.127634 | 0.038* | |
C7 | 0.2198 (2) | 0.37657 (7) | −0.0315 (2) | 0.0294 (4) | |
C8 | 0.3309 (3) | 0.37086 (9) | −0.1234 (3) | 0.0363 (5) | |
H8 | 0.323607 | 0.350007 | −0.190126 | 0.044* | |
C9 | 0.4523 (3) | 0.39572 (8) | −0.1171 (2) | 0.0342 (5) | |
H9 | 0.527480 | 0.391914 | −0.180609 | 0.041* | |
C10 | 0.7658 (2) | 0.35703 (6) | 0.3430 (2) | 0.0250 (4) | |
C11 | 0.6027 (2) | 0.36046 (7) | 0.3724 (2) | 0.0255 (4) | |
C12 | 0.5489 (3) | 0.38145 (8) | 0.4837 (3) | 0.0327 (5) | |
H12 | 0.613333 | 0.394634 | 0.544232 | 0.039* | |
C13 | 0.4001 (3) | 0.38318 (8) | 0.5068 (3) | 0.0372 (5) | |
H13 | 0.364338 | 0.397379 | 0.583268 | 0.045* | |
C14 | 0.3048 (3) | 0.36439 (8) | 0.4191 (3) | 0.0356 (5) | |
H14 | 0.203989 | 0.365700 | 0.435144 | 0.043* | |
C15 | 0.3575 (2) | 0.34366 (8) | 0.3077 (3) | 0.0316 (5) | |
H15 | 0.292724 | 0.330530 | 0.247400 | 0.038* | |
C16 | 0.5053 (2) | 0.34205 (7) | 0.2840 (2) | 0.0280 (4) | |
H16 | 0.540339 | 0.328194 | 0.206571 | 0.034* | |
C17 | 0.7998 (2) | 0.37806 (7) | 0.2062 (2) | 0.0257 (4) | |
C21 | 0.8580 (2) | 0.37934 (7) | 0.4503 (2) | 0.0294 (5) | |
C22 | 0.9215 (3) | 0.41771 (8) | 0.4283 (3) | 0.0413 (6) | |
H22 | 0.907919 | 0.431221 | 0.344617 | 0.050* | |
C23 | 1.0045 (3) | 0.43658 (9) | 0.5270 (4) | 0.0494 (7) | |
H23 | 1.047995 | 0.462634 | 0.509974 | 0.059* | |
C24 | 1.0239 (3) | 0.41755 (10) | 0.6499 (3) | 0.0455 (6) | |
H24 | 1.079810 | 0.430515 | 0.717847 | 0.055* | |
C25 | 0.9612 (4) | 0.37948 (11) | 0.6729 (3) | 0.0507 (7) | |
H25 | 0.974143 | 0.366164 | 0.757022 | 0.061* | |
C26 | 0.8794 (3) | 0.36060 (9) | 0.5737 (3) | 0.0425 (6) | |
H26 | 0.837388 | 0.334352 | 0.590724 | 0.051* | |
C31 | 0.8157 (2) | 0.31109 (7) | 0.3414 (2) | 0.0268 (4) | |
C32 | 0.7267 (3) | 0.27909 (7) | 0.3839 (2) | 0.0325 (5) | |
H32 | 0.629278 | 0.284828 | 0.406410 | 0.039* | |
C33 | 0.7780 (3) | 0.23889 (8) | 0.3941 (3) | 0.0390 (5) | |
H33 | 0.715377 | 0.217474 | 0.423345 | 0.047* | |
C34 | 0.9200 (3) | 0.22975 (8) | 0.3621 (3) | 0.0401 (5) | |
H34 | 0.954554 | 0.202170 | 0.367826 | 0.048* | |
C35 | 1.0104 (3) | 0.26135 (9) | 0.3216 (3) | 0.0401 (6) | |
H35 | 1.108089 | 0.255478 | 0.300460 | 0.048* | |
C36 | 0.9594 (3) | 0.30172 (8) | 0.3114 (3) | 0.0342 (5) | |
H36 | 1.022932 | 0.323134 | 0.283874 | 0.041* | |
Cl1 | 0.26471 (10) | 0.26888 (3) | −0.00483 (8) | 0.0606 (2) | |
Cl2 | 0.19862 (9) | 0.18556 (2) | 0.07558 (9) | 0.0586 (2) | |
Cl3 | 0.42228 (8) | 0.23128 (2) | 0.21146 (8) | 0.05236 (18) | |
C40 | 0.3369 (3) | 0.22237 (9) | 0.0572 (3) | 0.0458 (6) | |
H40 | 0.409547 | 0.211644 | −0.008309 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0596 (13) | 0.0607 (13) | 0.0387 (10) | −0.0353 (11) | 0.0151 (10) | −0.0071 (9) |
O2 | 0.0431 (10) | 0.0351 (9) | 0.0350 (9) | −0.0148 (7) | −0.0035 (7) | 0.0006 (7) |
O3 | 0.0317 (9) | 0.0547 (12) | 0.0516 (11) | 0.0148 (8) | 0.0169 (8) | 0.0188 (9) |
O4 | 0.0270 (8) | 0.0498 (10) | 0.0389 (9) | −0.0092 (7) | 0.0022 (7) | −0.0107 (8) |
N1 | 0.0225 (8) | 0.0265 (9) | 0.0292 (9) | 0.0001 (7) | 0.0036 (7) | 0.0023 (7) |
C1 | 0.0272 (10) | 0.0293 (11) | 0.0288 (11) | −0.0056 (8) | 0.0003 (8) | 0.0011 (9) |
C2 | 0.0252 (9) | 0.0263 (10) | 0.0299 (10) | −0.0048 (8) | −0.0002 (8) | 0.0025 (8) |
C3 | 0.0319 (12) | 0.0290 (11) | 0.0437 (13) | −0.0041 (9) | −0.0059 (10) | 0.0106 (10) |
C4 | 0.0259 (10) | 0.0291 (11) | 0.0367 (12) | −0.0004 (9) | −0.0069 (9) | 0.0081 (9) |
C5 | 0.0346 (11) | 0.0284 (11) | 0.0364 (12) | 0.0019 (9) | −0.0030 (10) | −0.0016 (9) |
C6 | 0.0281 (10) | 0.0340 (11) | 0.0321 (10) | 0.0041 (9) | 0.0011 (9) | 0.0009 (9) |
C7 | 0.0218 (9) | 0.0346 (11) | 0.0317 (11) | −0.0003 (9) | −0.0024 (8) | 0.0006 (9) |
C8 | 0.0299 (11) | 0.0455 (14) | 0.0335 (12) | −0.0026 (10) | 0.0006 (9) | −0.0087 (10) |
C9 | 0.0257 (10) | 0.0436 (13) | 0.0332 (11) | −0.0010 (10) | 0.0018 (9) | 0.0009 (10) |
C10 | 0.0202 (9) | 0.0242 (10) | 0.0306 (10) | 0.0004 (8) | 0.0009 (8) | 0.0011 (8) |
C11 | 0.0237 (10) | 0.0236 (10) | 0.0292 (10) | 0.0000 (8) | 0.0021 (8) | 0.0049 (8) |
C12 | 0.0296 (11) | 0.0310 (11) | 0.0375 (12) | −0.0002 (9) | 0.0029 (9) | −0.0031 (9) |
C13 | 0.0321 (12) | 0.0369 (12) | 0.0425 (13) | 0.0049 (10) | 0.0108 (10) | −0.0042 (10) |
C14 | 0.0245 (10) | 0.0342 (12) | 0.0482 (14) | 0.0034 (9) | 0.0081 (10) | 0.0058 (10) |
C15 | 0.0255 (10) | 0.0312 (11) | 0.0381 (12) | −0.0025 (9) | 0.0003 (9) | 0.0051 (9) |
C16 | 0.0255 (10) | 0.0269 (10) | 0.0316 (10) | −0.0015 (8) | 0.0007 (9) | 0.0014 (9) |
C17 | 0.0204 (9) | 0.0247 (10) | 0.0319 (10) | −0.0013 (8) | 0.0012 (8) | −0.0002 (8) |
C21 | 0.0232 (9) | 0.0303 (11) | 0.0347 (11) | 0.0016 (8) | −0.0029 (8) | −0.0039 (9) |
C22 | 0.0411 (13) | 0.0323 (12) | 0.0505 (14) | −0.0033 (10) | −0.0128 (12) | 0.0022 (11) |
C23 | 0.0475 (15) | 0.0333 (13) | 0.0673 (19) | −0.0049 (12) | −0.0184 (14) | −0.0048 (13) |
C24 | 0.0389 (13) | 0.0497 (16) | 0.0478 (15) | 0.0036 (12) | −0.0127 (12) | −0.0173 (13) |
C25 | 0.0550 (17) | 0.0630 (18) | 0.0340 (13) | −0.0098 (15) | −0.0076 (12) | 0.0000 (13) |
C26 | 0.0466 (14) | 0.0467 (15) | 0.0343 (12) | −0.0098 (12) | −0.0042 (11) | 0.0031 (11) |
C31 | 0.0265 (10) | 0.0257 (10) | 0.0282 (10) | 0.0026 (8) | −0.0007 (8) | 0.0006 (8) |
C32 | 0.0278 (11) | 0.0301 (11) | 0.0396 (12) | 0.0017 (9) | 0.0008 (9) | 0.0045 (9) |
C33 | 0.0429 (13) | 0.0282 (12) | 0.0460 (13) | −0.0012 (10) | −0.0054 (11) | 0.0049 (10) |
C34 | 0.0454 (14) | 0.0280 (11) | 0.0468 (13) | 0.0109 (11) | −0.0078 (11) | −0.0010 (11) |
C35 | 0.0334 (12) | 0.0405 (14) | 0.0465 (14) | 0.0132 (10) | −0.0022 (10) | 0.0010 (11) |
C36 | 0.0282 (11) | 0.0342 (12) | 0.0403 (12) | 0.0036 (9) | −0.0019 (9) | 0.0015 (10) |
Cl1 | 0.0768 (5) | 0.0522 (4) | 0.0529 (4) | 0.0030 (4) | −0.0042 (4) | 0.0110 (3) |
Cl2 | 0.0607 (4) | 0.0443 (4) | 0.0710 (5) | −0.0099 (3) | −0.0009 (4) | −0.0135 (3) |
Cl3 | 0.0508 (4) | 0.0434 (3) | 0.0629 (4) | 0.0023 (3) | −0.0125 (3) | −0.0037 (3) |
C40 | 0.0485 (15) | 0.0414 (14) | 0.0475 (14) | 0.0018 (12) | 0.0065 (12) | −0.0073 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.257 (3) | C13—C14 | 1.384 (4) |
O1—H1 | 0.8400 | C13—H13 | 0.9500 |
O2—C1 | 1.256 (3) | C14—C15 | 1.386 (4) |
O2—H2 | 0.8400 | C14—H14 | 0.9500 |
O3—C17 | 1.227 (3) | C15—C16 | 1.392 (3) |
O4—C7 | 1.359 (3) | C15—H15 | 0.9500 |
O4—H4 | 0.8400 | C16—H16 | 0.9500 |
N1—C17 | 1.334 (3) | C21—C26 | 1.385 (4) |
N1—C2 | 1.459 (3) | C21—C22 | 1.392 (4) |
N1—H1A | 0.8800 | C22—C23 | 1.390 (4) |
C1—C2 | 1.523 (3) | C22—H22 | 0.9500 |
C2—C3 | 1.535 (3) | C23—C24 | 1.382 (5) |
C2—H2A | 1.0000 | C23—H23 | 0.9500 |
C3—C4 | 1.509 (3) | C24—C25 | 1.381 (5) |
C3—H3A | 0.9900 | C24—H24 | 0.9500 |
C3—H3B | 0.9900 | C25—C26 | 1.388 (4) |
C4—C9 | 1.391 (4) | C25—H25 | 0.9500 |
C4—C5 | 1.391 (4) | C26—H26 | 0.9500 |
C5—C6 | 1.384 (3) | C31—C32 | 1.391 (3) |
C5—H5 | 0.9500 | C31—C36 | 1.400 (3) |
C6—C7 | 1.388 (3) | C32—C33 | 1.389 (4) |
C6—H6 | 0.9500 | C32—H32 | 0.9500 |
C7—C8 | 1.391 (3) | C33—C34 | 1.387 (4) |
C8—C9 | 1.386 (4) | C33—H33 | 0.9500 |
C8—H8 | 0.9500 | C34—C35 | 1.383 (4) |
C9—H9 | 0.9500 | C34—H34 | 0.9500 |
C10—C11 | 1.546 (3) | C35—C36 | 1.393 (4) |
C10—C21 | 1.548 (3) | C35—H35 | 0.9500 |
C10—C17 | 1.555 (3) | C36—H36 | 0.9500 |
C10—C31 | 1.557 (3) | Cl1—C40 | 1.759 (3) |
C11—C12 | 1.393 (3) | Cl2—C40 | 1.760 (3) |
C11—C16 | 1.395 (3) | Cl3—C40 | 1.753 (3) |
C12—C13 | 1.400 (3) | C40—H40 | 1.0000 |
C12—H12 | 0.9500 | | |
| | | |
C1—O1—H1 | 109.5 | C13—C14—C15 | 119.5 (2) |
C1—O2—H2 | 109.5 | C13—C14—H14 | 120.2 |
C7—O4—H4 | 109.5 | C15—C14—H14 | 120.2 |
C17—N1—C2 | 121.05 (19) | C14—C15—C16 | 120.1 (2) |
C17—N1—H1A | 119.5 | C14—C15—H15 | 120.0 |
C2—N1—H1A | 119.5 | C16—C15—H15 | 120.0 |
O2—C1—O1 | 124.7 (2) | C15—C16—C11 | 121.0 (2) |
O2—C1—C2 | 119.6 (2) | C15—C16—H16 | 119.5 |
O1—C1—C2 | 115.5 (2) | C11—C16—H16 | 119.5 |
N1—C2—C1 | 112.59 (18) | O3—C17—N1 | 119.6 (2) |
N1—C2—C3 | 110.36 (18) | O3—C17—C10 | 121.7 (2) |
C1—C2—C3 | 106.58 (18) | N1—C17—C10 | 118.47 (18) |
N1—C2—H2A | 109.1 | C26—C21—C22 | 118.0 (2) |
C1—C2—H2A | 109.1 | C26—C21—C10 | 119.3 (2) |
C3—C2—H2A | 109.1 | C22—C21—C10 | 122.8 (2) |
C4—C3—C2 | 113.13 (19) | C23—C22—C21 | 121.0 (3) |
C4—C3—H3A | 109.0 | C23—C22—H22 | 119.5 |
C2—C3—H3A | 109.0 | C21—C22—H22 | 119.5 |
C4—C3—H3B | 109.0 | C24—C23—C22 | 120.2 (3) |
C2—C3—H3B | 109.0 | C24—C23—H23 | 119.9 |
H3A—C3—H3B | 107.8 | C22—C23—H23 | 119.9 |
C9—C4—C5 | 118.4 (2) | C25—C24—C23 | 119.3 (3) |
C9—C4—C3 | 120.8 (2) | C25—C24—H24 | 120.4 |
C5—C4—C3 | 120.8 (2) | C23—C24—H24 | 120.4 |
C6—C5—C4 | 121.1 (2) | C24—C25—C26 | 120.3 (3) |
C6—C5—H5 | 119.5 | C24—C25—H25 | 119.8 |
C4—C5—H5 | 119.5 | C26—C25—H25 | 119.8 |
C5—C6—C7 | 119.9 (2) | C21—C26—C25 | 121.2 (3) |
C5—C6—H6 | 120.0 | C21—C26—H26 | 119.4 |
C7—C6—H6 | 120.0 | C25—C26—H26 | 119.4 |
O4—C7—C6 | 122.4 (2) | C32—C31—C36 | 118.0 (2) |
O4—C7—C8 | 117.9 (2) | C32—C31—C10 | 122.06 (19) |
C6—C7—C8 | 119.7 (2) | C36—C31—C10 | 119.5 (2) |
C9—C8—C7 | 119.7 (2) | C33—C32—C31 | 121.1 (2) |
C9—C8—H8 | 120.1 | C33—C32—H32 | 119.5 |
C7—C8—H8 | 120.1 | C31—C32—H32 | 119.5 |
C8—C9—C4 | 121.1 (2) | C34—C33—C32 | 120.5 (3) |
C8—C9—H9 | 119.4 | C34—C33—H33 | 119.7 |
C4—C9—H9 | 119.4 | C32—C33—H33 | 119.7 |
C11—C10—C21 | 112.13 (18) | C35—C34—C33 | 119.0 (2) |
C11—C10—C17 | 109.46 (17) | C35—C34—H34 | 120.5 |
C21—C10—C17 | 106.82 (17) | C33—C34—H34 | 120.5 |
C11—C10—C31 | 111.22 (17) | C34—C35—C36 | 120.6 (2) |
C21—C10—C31 | 106.73 (17) | C34—C35—H35 | 119.7 |
C17—C10—C31 | 110.37 (18) | C36—C35—H35 | 119.7 |
C12—C11—C16 | 118.6 (2) | C35—C36—C31 | 120.7 (2) |
C12—C11—C10 | 122.4 (2) | C35—C36—H36 | 119.6 |
C16—C11—C10 | 119.0 (2) | C31—C36—H36 | 119.6 |
C11—C12—C13 | 120.2 (2) | Cl3—C40—Cl1 | 109.83 (16) |
C11—C12—H12 | 119.9 | Cl3—C40—Cl2 | 110.43 (17) |
C13—C12—H12 | 119.9 | Cl1—C40—Cl2 | 109.74 (17) |
C14—C13—C12 | 120.6 (2) | Cl3—C40—H40 | 108.9 |
C14—C13—H13 | 119.7 | Cl1—C40—H40 | 108.9 |
C12—C13—H13 | 119.7 | Cl2—C40—H40 | 108.9 |
| | | |
C17—N1—C2—C1 | −71.4 (3) | C2—N1—C17—C10 | −179.99 (18) |
C17—N1—C2—C3 | 169.6 (2) | C11—C10—C17—O3 | −162.5 (2) |
O2—C1—C2—N1 | −24.0 (3) | C21—C10—C17—O3 | 75.9 (3) |
O1—C1—C2—N1 | 160.9 (2) | C31—C10—C17—O3 | −39.7 (3) |
O2—C1—C2—C3 | 97.1 (3) | C11—C10—C17—N1 | 22.5 (3) |
O1—C1—C2—C3 | −77.9 (3) | C21—C10—C17—N1 | −99.1 (2) |
N1—C2—C3—C4 | −56.3 (3) | C31—C10—C17—N1 | 145.21 (19) |
C1—C2—C3—C4 | −178.9 (2) | C11—C10—C21—C26 | 77.1 (3) |
C2—C3—C4—C9 | −67.2 (3) | C17—C10—C21—C26 | −163.0 (2) |
C2—C3—C4—C5 | 111.6 (3) | C31—C10—C21—C26 | −44.9 (3) |
C9—C4—C5—C6 | 0.3 (4) | C11—C10—C21—C22 | −103.1 (3) |
C3—C4—C5—C6 | −178.5 (2) | C17—C10—C21—C22 | 16.8 (3) |
C4—C5—C6—C7 | 0.6 (4) | C31—C10—C21—C22 | 134.9 (2) |
C5—C6—C7—O4 | 177.9 (2) | C26—C21—C22—C23 | 0.3 (4) |
C5—C6—C7—C8 | −0.8 (4) | C10—C21—C22—C23 | −179.5 (3) |
O4—C7—C8—C9 | −178.6 (2) | C21—C22—C23—C24 | −0.7 (5) |
C6—C7—C8—C9 | 0.2 (4) | C22—C23—C24—C25 | 0.6 (5) |
C7—C8—C9—C4 | 0.7 (4) | C23—C24—C25—C26 | −0.1 (5) |
C5—C4—C9—C8 | −1.0 (4) | C22—C21—C26—C25 | 0.3 (4) |
C3—C4—C9—C8 | 177.9 (2) | C10—C21—C26—C25 | −180.0 (3) |
C21—C10—C11—C12 | 0.0 (3) | C24—C25—C26—C21 | −0.4 (5) |
C17—C10—C11—C12 | −118.4 (2) | C11—C10—C31—C32 | −10.0 (3) |
C31—C10—C11—C12 | 119.4 (2) | C21—C10—C31—C32 | 112.6 (2) |
C21—C10—C11—C16 | 179.68 (19) | C17—C10—C31—C32 | −131.7 (2) |
C17—C10—C11—C16 | 61.3 (3) | C11—C10—C31—C36 | 177.7 (2) |
C31—C10—C11—C16 | −60.9 (3) | C21—C10—C31—C36 | −59.7 (3) |
C16—C11—C12—C13 | 1.1 (4) | C17—C10—C31—C36 | 56.0 (3) |
C10—C11—C12—C13 | −179.2 (2) | C36—C31—C32—C33 | −1.2 (4) |
C11—C12—C13—C14 | −0.5 (4) | C10—C31—C32—C33 | −173.6 (2) |
C12—C13—C14—C15 | 0.1 (4) | C31—C32—C33—C34 | 0.1 (4) |
C13—C14—C15—C16 | −0.4 (4) | C32—C33—C34—C35 | 0.9 (4) |
C14—C15—C16—C11 | 1.1 (4) | C33—C34—C35—C36 | −0.8 (4) |
C12—C11—C16—C15 | −1.5 (3) | C34—C35—C36—C31 | −0.3 (4) |
C10—C11—C16—C15 | 178.8 (2) | C32—C31—C36—C35 | 1.3 (4) |
C2—N1—C17—O3 | 4.9 (3) | C10—C31—C36—C35 | 173.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.84 | 1.83 | 2.635 (4) | 160 |
O2—H2···O2i | 0.84 | 1.80 | 2.627 (3) | 169 |
O4—H4···O3ii | 0.84 | 1.80 | 2.642 (3) | 176 |
C36—H36···O3 | 0.95 | 2.32 | 2.825 (3) | 113 |
C25—H25···O4iii | 0.95 | 2.41 | 3.292 (4) | 154 |
Symmetry codes: (i) −x+2, −y+1, z; (ii) x−1, y, z; (iii) x+1, y, z+1. |
N-Triphenylacetyl-
L-tyrosine dichloromethane 0.1-solvate (IV)
top
Crystal data top
C29H25NO4·0.1CH2Cl2 | Dx = 1.306 Mg m−3 |
Mr = 459.99 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 19362 reflections |
a = 9.28862 (9) Å | θ = 3.6–76.1° |
b = 10.34013 (9) Å | µ = 0.90 mm−1 |
c = 24.3525 (2) Å | T = 130 K |
V = 2338.95 (4) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.15 × 0.03 mm |
F(000) = 969 | |
Data collection top
Rigaku SuperNova Single Source diffractometer with an Atlas detector | 4276 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 4225 reflections with I > 2σ(I) |
Detector resolution: 10.5357 pixels mm-1 | Rint = 0.024 |
ω scans | θmax = 68.3°, θmin = 4.7° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | h = −11→11 |
Tmin = 0.882, Tmax = 1.000 | k = −12→12 |
30278 measured reflections | l = −29→29 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.354P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.086 | (Δ/σ)max = 0.042 |
S = 1.05 | Δρmax = 0.13 e Å−3 |
4276 reflections | Δρmin = −0.14 e Å−3 |
494 parameters | Absolute structure: Flack x determined using 1770 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
154 restraints | Absolute structure parameter: 0.03 (3) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The diffraction data for all monocrystals were collected at 130 K
with an Oxford Diffraction SuperNova diffractometer using Cu Kα radiation
(λ = 1.54184 Å). The intensity data were collected and processed with
the use of CrysAlis PRO software (1.171.40.67a). The structures were
solved by
direct methods with the program SHELXT2018 (Sheldrick, 2015b) and
refined by full-matrix least-squares method on F2 with SHELXL2018
(Sheldrick, 2015a). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.81412 (17) | 0.12891 (13) | 0.53011 (6) | 0.0432 (3) | |
H1 | 0.780708 | 0.056091 | 0.538587 | 0.065* | |
O2 | 0.6365 (2) | 0.12919 (15) | 0.46714 (7) | 0.0602 (5) | |
O3 | 0.90095 (15) | 0.45792 (14) | 0.40994 (6) | 0.0416 (3) | |
O4 | 0.65854 (17) | 0.92669 (13) | 0.56752 (7) | 0.0450 (4) | |
H4 | 0.573687 | 0.954072 | 0.570224 | 0.068* | |
N1 | 0.68897 (18) | 0.38401 (15) | 0.44215 (6) | 0.0359 (4) | |
H1A | 0.595532 | 0.379204 | 0.436546 | 0.043* | |
C1 | 0.7276 (2) | 0.1853 (2) | 0.49351 (9) | 0.0405 (5) | |
C2 | 0.7471 (2) | 0.33120 (18) | 0.49275 (8) | 0.0352 (4) | |
H2 | 0.851587 | 0.353161 | 0.495885 | 0.042* | |
C3 | 0.6654 (2) | 0.38112 (18) | 0.54362 (8) | 0.0363 (4) | |
H3A | 0.564886 | 0.349622 | 0.541929 | 0.044* | |
H3B | 0.710279 | 0.343741 | 0.576911 | 0.044* | |
C4 | 0.6635 (2) | 0.52648 (18) | 0.54917 (7) | 0.0325 (4) | |
C5 | 0.5338 (2) | 0.59212 (19) | 0.55357 (9) | 0.0361 (4) | |
H5 | 0.446154 | 0.544931 | 0.552097 | 0.043* | |
C6 | 0.5296 (2) | 0.7259 (2) | 0.56010 (9) | 0.0370 (4) | |
H6 | 0.439984 | 0.769486 | 0.563206 | 0.044* | |
C7 | 0.6570 (2) | 0.79456 (18) | 0.56202 (8) | 0.0347 (4) | |
C8 | 0.7878 (2) | 0.73115 (19) | 0.55772 (9) | 0.0384 (4) | |
H8 | 0.875349 | 0.778602 | 0.558997 | 0.046* | |
C9 | 0.7901 (2) | 0.59794 (19) | 0.55154 (8) | 0.0367 (4) | |
H9 | 0.880008 | 0.554587 | 0.548859 | 0.044* | |
C10 | 0.6910 (2) | 0.4888 (2) | 0.35103 (8) | 0.0372 (4) | |
C17 | 0.7711 (2) | 0.43977 (18) | 0.40353 (8) | 0.0349 (4) | |
C11 | 0.7926 (3) | 0.4808 (3) | 0.29815 (10) | 0.0414 (10) | 0.763 (4) |
C16 | 0.9179 (3) | 0.5541 (3) | 0.29683 (9) | 0.0437 (8) | 0.763 (4) |
H16 | 0.943800 | 0.605756 | 0.327561 | 0.052* | 0.763 (4) |
C15 | 1.0055 (2) | 0.5519 (3) | 0.25055 (10) | 0.0553 (9) | 0.763 (4) |
H15 | 1.091198 | 0.602022 | 0.249653 | 0.066* | 0.763 (4) |
C14 | 0.9677 (3) | 0.4764 (4) | 0.20560 (9) | 0.0625 (11) | 0.763 (4) |
H14 | 1.027510 | 0.474882 | 0.173966 | 0.075* | 0.763 (4) |
C13 | 0.8423 (4) | 0.4031 (3) | 0.20691 (10) | 0.0594 (11) | 0.763 (4) |
H13 | 0.816424 | 0.351474 | 0.176186 | 0.071* | 0.763 (4) |
C12 | 0.7547 (3) | 0.4053 (3) | 0.25319 (12) | 0.0460 (9) | 0.763 (4) |
H12 | 0.669024 | 0.355207 | 0.254094 | 0.055* | 0.763 (4) |
C21 | 0.5483 (5) | 0.4157 (6) | 0.3436 (3) | 0.0375 (9) | 0.829 (14) |
C22 | 0.4158 (6) | 0.4766 (6) | 0.3397 (3) | 0.0453 (10) | 0.829 (14) |
H22 | 0.410409 | 0.568079 | 0.342418 | 0.054* | 0.829 (14) |
C23 | 0.2906 (5) | 0.4050 (7) | 0.3317 (2) | 0.0541 (13) | 0.829 (14) |
H23 | 0.200490 | 0.447964 | 0.328811 | 0.065* | 0.829 (14) |
C24 | 0.2966 (6) | 0.2725 (6) | 0.32788 (17) | 0.0538 (13) | 0.829 (14) |
H24 | 0.211023 | 0.224072 | 0.321910 | 0.065* | 0.829 (14) |
C25 | 0.4270 (6) | 0.2099 (5) | 0.33276 (19) | 0.0521 (11) | 0.829 (14) |
H25 | 0.431224 | 0.118259 | 0.330882 | 0.063* | 0.829 (14) |
C26 | 0.5515 (6) | 0.2806 (6) | 0.3404 (3) | 0.0449 (9) | 0.829 (14) |
H26 | 0.640945 | 0.236642 | 0.343480 | 0.054* | 0.829 (14) |
C31 | 0.6672 (5) | 0.6367 (3) | 0.35907 (16) | 0.0343 (9) | 0.829 (14) |
C32 | 0.6415 (6) | 0.7160 (3) | 0.31376 (13) | 0.0484 (10) | 0.829 (14) |
H32 | 0.636198 | 0.678291 | 0.278247 | 0.058* | 0.829 (14) |
C33 | 0.6237 (7) | 0.8479 (3) | 0.31926 (14) | 0.0523 (11) | 0.829 (14) |
H33 | 0.605653 | 0.899437 | 0.287718 | 0.063* | 0.829 (14) |
C34 | 0.6319 (4) | 0.9054 (3) | 0.37046 (17) | 0.0433 (9) | 0.829 (14) |
H34 | 0.622816 | 0.996466 | 0.374169 | 0.052* | 0.829 (14) |
C35 | 0.6534 (5) | 0.8288 (4) | 0.41593 (13) | 0.0343 (8) | 0.829 (14) |
H35 | 0.657887 | 0.867158 | 0.451346 | 0.041* | 0.829 (14) |
C36 | 0.6687 (4) | 0.6956 (4) | 0.41036 (13) | 0.0312 (8) | 0.829 (14) |
H36 | 0.680341 | 0.643810 | 0.442277 | 0.037* | 0.829 (14) |
C11A | 0.7701 (15) | 0.4251 (16) | 0.3026 (5) | 0.056 (4) | 0.144 (3) |
C16A | 0.9088 (14) | 0.3750 (16) | 0.3045 (4) | 0.062 (3) | 0.144 (3) |
H16A | 0.958183 | 0.369117 | 0.338585 | 0.075* | 0.144 (3) |
C15A | 0.9754 (12) | 0.3335 (16) | 0.2565 (5) | 0.067 (3) | 0.144 (3) |
H15A | 1.070217 | 0.299234 | 0.257799 | 0.080* | 0.144 (3) |
C14A | 0.9032 (17) | 0.3421 (18) | 0.2067 (4) | 0.067 (3) | 0.144 (3) |
H14A | 0.948650 | 0.313743 | 0.173864 | 0.080* | 0.144 (3) |
C13A | 0.7644 (17) | 0.3922 (19) | 0.2048 (5) | 0.065 (4) | 0.144 (3) |
H13A | 0.715048 | 0.398135 | 0.170716 | 0.078* | 0.144 (3) |
C12A | 0.6978 (13) | 0.4338 (17) | 0.2528 (6) | 0.058 (4) | 0.144 (3) |
H12A | 0.603011 | 0.468018 | 0.251502 | 0.070* | 0.144 (3) |
C21A | 0.537 (2) | 0.426 (4) | 0.3452 (17) | 0.059 (6) | 0.171 (14) |
C22A | 0.418 (3) | 0.506 (3) | 0.3406 (15) | 0.057 (5) | 0.171 (14) |
H22A | 0.428916 | 0.597581 | 0.342072 | 0.069* | 0.171 (14) |
C23A | 0.282 (3) | 0.453 (3) | 0.3337 (11) | 0.059 (5) | 0.171 (14) |
H23A | 0.199892 | 0.507319 | 0.330530 | 0.071* | 0.171 (14) |
C24A | 0.265 (2) | 0.319 (3) | 0.3315 (9) | 0.061 (5) | 0.171 (14) |
H24A | 0.172414 | 0.282540 | 0.326794 | 0.073* | 0.171 (14) |
C25A | 0.385 (3) | 0.239 (3) | 0.3361 (11) | 0.061 (5) | 0.171 (14) |
H25A | 0.373959 | 0.148020 | 0.334601 | 0.073* | 0.171 (14) |
C26A | 0.521 (2) | 0.293 (3) | 0.3430 (15) | 0.061 (5) | 0.171 (14) |
H26A | 0.602985 | 0.238280 | 0.346143 | 0.073* | 0.171 (14) |
C31A | 0.680 (3) | 0.6295 (15) | 0.3580 (9) | 0.059 (5) | 0.171 (14) |
C32A | 0.705 (3) | 0.7055 (17) | 0.3119 (7) | 0.061 (4) | 0.171 (14) |
H32A | 0.727266 | 0.665957 | 0.277731 | 0.073* | 0.171 (14) |
C33A | 0.699 (3) | 0.8395 (16) | 0.3159 (6) | 0.062 (4) | 0.171 (14) |
H33A | 0.715935 | 0.891478 | 0.284434 | 0.074* | 0.171 (14) |
C34A | 0.667 (3) | 0.8974 (16) | 0.3660 (9) | 0.061 (4) | 0.171 (14) |
H34A | 0.661990 | 0.988945 | 0.368678 | 0.074* | 0.171 (14) |
C35A | 0.641 (3) | 0.821 (2) | 0.4120 (7) | 0.060 (5) | 0.171 (14) |
H35A | 0.619376 | 0.860892 | 0.446218 | 0.072* | 0.171 (14) |
C36A | 0.648 (3) | 0.687 (2) | 0.4080 (8) | 0.059 (5) | 0.171 (14) |
H36A | 0.630707 | 0.635371 | 0.439516 | 0.071* | 0.171 (14) |
C18 | 0.708 (2) | 0.389 (3) | 0.2571 (9) | 0.035 (4) | 0.093 (4) |
H18 | 0.612033 | 0.359189 | 0.261294 | 0.043* | 0.093 (4) |
C1D | 0.776 (2) | 0.452 (3) | 0.3004 (7) | 0.032 (4) | 0.093 (4) |
C1C | 0.917 (2) | 0.496 (2) | 0.2943 (6) | 0.035 (4) | 0.093 (4) |
H1C | 0.963353 | 0.538977 | 0.323864 | 0.042* | 0.093 (4) |
C1B | 0.9888 (18) | 0.478 (2) | 0.2449 (7) | 0.038 (4) | 0.093 (4) |
H1B | 1.084821 | 0.507939 | 0.240721 | 0.045* | 0.093 (4) |
C1A | 0.921 (2) | 0.415 (2) | 0.2016 (5) | 0.037 (4) | 0.093 (4) |
H1AA | 0.969896 | 0.402526 | 0.167864 | 0.044* | 0.093 (4) |
C19 | 0.780 (2) | 0.371 (2) | 0.2077 (7) | 0.038 (4) | 0.093 (4) |
H19 | 0.733503 | 0.328150 | 0.178149 | 0.046* | 0.093 (4) |
Cl5 | 0.9214 (7) | 0.1498 (9) | 0.3459 (3) | 0.0736 (19) | 0.1 |
Cl6 | 0.7883 (10) | 0.1174 (7) | 0.2394 (4) | 0.079 (2) | 0.1 |
C20 | 0.941 (2) | 0.161 (2) | 0.2748 (9) | 0.062 (7) | 0.1 |
H20A | 0.966618 | 0.251690 | 0.265168 | 0.074* | 0.1 |
H20B | 1.022095 | 0.105311 | 0.263115 | 0.074* | 0.1 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0504 (8) | 0.0294 (6) | 0.0498 (8) | 0.0032 (6) | −0.0004 (7) | 0.0033 (6) |
O2 | 0.0856 (13) | 0.0333 (7) | 0.0616 (10) | −0.0052 (8) | −0.0205 (10) | −0.0058 (7) |
O3 | 0.0399 (8) | 0.0427 (8) | 0.0421 (8) | −0.0027 (6) | −0.0075 (6) | 0.0033 (6) |
O4 | 0.0437 (8) | 0.0261 (6) | 0.0653 (9) | 0.0015 (6) | 0.0052 (7) | −0.0036 (6) |
N1 | 0.0383 (8) | 0.0368 (8) | 0.0326 (8) | 0.0011 (7) | −0.0038 (7) | −0.0025 (6) |
C1 | 0.0516 (12) | 0.0302 (10) | 0.0397 (10) | 0.0019 (9) | 0.0002 (9) | −0.0060 (8) |
C2 | 0.0434 (10) | 0.0285 (9) | 0.0337 (9) | 0.0031 (8) | −0.0036 (8) | −0.0015 (7) |
C3 | 0.0463 (11) | 0.0283 (9) | 0.0342 (9) | −0.0001 (8) | 0.0004 (8) | 0.0006 (7) |
C4 | 0.0425 (10) | 0.0290 (9) | 0.0261 (8) | 0.0018 (8) | −0.0004 (8) | −0.0005 (7) |
C5 | 0.0374 (10) | 0.0330 (10) | 0.0379 (10) | −0.0041 (8) | −0.0004 (8) | −0.0028 (8) |
C6 | 0.0362 (10) | 0.0344 (10) | 0.0404 (10) | 0.0042 (8) | 0.0008 (8) | −0.0027 (8) |
C7 | 0.0406 (10) | 0.0286 (9) | 0.0349 (9) | −0.0007 (8) | 0.0014 (8) | −0.0013 (7) |
C8 | 0.0359 (10) | 0.0335 (10) | 0.0459 (11) | −0.0024 (8) | 0.0001 (8) | −0.0029 (8) |
C9 | 0.0373 (10) | 0.0335 (10) | 0.0394 (10) | 0.0041 (8) | −0.0016 (8) | −0.0031 (8) |
C10 | 0.0388 (10) | 0.0437 (11) | 0.0290 (9) | 0.0043 (9) | −0.0021 (8) | −0.0043 (8) |
C17 | 0.0424 (11) | 0.0296 (9) | 0.0329 (9) | 0.0041 (8) | −0.0028 (8) | −0.0063 (8) |
C11 | 0.044 (2) | 0.048 (2) | 0.0321 (16) | 0.0104 (14) | −0.0009 (13) | 0.0011 (13) |
C16 | 0.0424 (15) | 0.0514 (19) | 0.0373 (15) | 0.0053 (16) | 0.0002 (12) | 0.0043 (14) |
C15 | 0.0467 (16) | 0.076 (3) | 0.0437 (16) | 0.0019 (17) | 0.0021 (13) | 0.0114 (18) |
C14 | 0.055 (2) | 0.096 (3) | 0.0365 (19) | 0.011 (2) | 0.0111 (15) | 0.0046 (19) |
C13 | 0.055 (3) | 0.087 (3) | 0.0361 (16) | 0.014 (2) | 0.0060 (18) | −0.0078 (17) |
C12 | 0.050 (2) | 0.054 (2) | 0.0350 (19) | 0.0054 (17) | 0.0036 (15) | −0.0035 (15) |
C21 | 0.0434 (16) | 0.0433 (19) | 0.0258 (15) | −0.0003 (13) | −0.0045 (13) | −0.0050 (12) |
C22 | 0.042 (2) | 0.054 (2) | 0.0400 (18) | 0.0022 (16) | −0.0021 (14) | −0.0071 (17) |
C23 | 0.0427 (17) | 0.077 (4) | 0.0431 (18) | 0.001 (2) | −0.0019 (13) | −0.009 (2) |
C24 | 0.052 (2) | 0.072 (3) | 0.0372 (15) | −0.020 (2) | −0.0024 (15) | −0.0076 (18) |
C25 | 0.071 (3) | 0.051 (2) | 0.0350 (16) | −0.012 (2) | −0.0099 (18) | −0.0046 (15) |
C26 | 0.056 (2) | 0.0442 (17) | 0.0348 (16) | −0.0034 (16) | −0.0097 (17) | −0.0046 (13) |
C31 | 0.0360 (18) | 0.0362 (14) | 0.0306 (15) | 0.0009 (13) | −0.0036 (12) | 0.0024 (12) |
C32 | 0.066 (3) | 0.0499 (17) | 0.0298 (13) | 0.0085 (16) | −0.0052 (15) | 0.0031 (12) |
C33 | 0.067 (3) | 0.0477 (16) | 0.0419 (15) | 0.0102 (16) | −0.0011 (16) | 0.0167 (13) |
C34 | 0.046 (2) | 0.0342 (15) | 0.0499 (18) | 0.0026 (12) | 0.0017 (13) | 0.0069 (12) |
C35 | 0.0308 (16) | 0.0333 (14) | 0.0389 (15) | 0.0014 (12) | −0.0005 (12) | 0.0019 (12) |
C36 | 0.0298 (16) | 0.0326 (15) | 0.0310 (14) | 0.0022 (11) | −0.0001 (11) | 0.0032 (10) |
C11A | 0.054 (6) | 0.076 (8) | 0.040 (6) | 0.023 (6) | 0.006 (5) | 0.008 (5) |
C16A | 0.059 (6) | 0.081 (7) | 0.047 (6) | 0.020 (6) | 0.006 (5) | −0.004 (5) |
C15A | 0.065 (6) | 0.086 (7) | 0.050 (6) | 0.020 (6) | 0.006 (5) | −0.003 (5) |
C14A | 0.067 (7) | 0.086 (7) | 0.049 (6) | 0.022 (6) | 0.009 (5) | 0.001 (5) |
C13A | 0.067 (7) | 0.082 (8) | 0.047 (6) | 0.025 (6) | 0.006 (6) | 0.006 (6) |
C12A | 0.061 (7) | 0.074 (7) | 0.040 (6) | 0.028 (6) | 0.007 (6) | 0.010 (5) |
C21A | 0.063 (9) | 0.071 (11) | 0.043 (7) | 0.005 (8) | −0.016 (6) | −0.009 (7) |
C22A | 0.058 (9) | 0.073 (11) | 0.042 (7) | 0.005 (8) | −0.019 (6) | −0.006 (8) |
C23A | 0.062 (8) | 0.072 (11) | 0.043 (7) | 0.007 (8) | −0.017 (5) | −0.005 (7) |
C24A | 0.065 (8) | 0.071 (11) | 0.046 (7) | 0.008 (8) | −0.013 (6) | −0.007 (7) |
C25A | 0.067 (9) | 0.070 (11) | 0.047 (7) | 0.007 (8) | −0.013 (6) | −0.007 (7) |
C26A | 0.066 (9) | 0.072 (11) | 0.045 (7) | 0.009 (8) | −0.013 (6) | −0.008 (7) |
C31A | 0.057 (9) | 0.071 (8) | 0.049 (7) | −0.009 (7) | 0.007 (6) | 0.005 (7) |
C32A | 0.062 (8) | 0.070 (7) | 0.050 (6) | −0.009 (7) | 0.006 (6) | 0.005 (6) |
C33A | 0.064 (8) | 0.070 (7) | 0.051 (6) | −0.010 (7) | 0.006 (6) | 0.006 (6) |
C34A | 0.060 (8) | 0.067 (8) | 0.057 (7) | −0.010 (6) | 0.005 (6) | 0.004 (6) |
C35A | 0.057 (8) | 0.069 (8) | 0.055 (7) | −0.008 (7) | 0.006 (6) | 0.003 (7) |
C36A | 0.055 (9) | 0.069 (8) | 0.053 (7) | −0.007 (7) | 0.007 (6) | 0.006 (7) |
C18 | 0.045 (9) | 0.048 (8) | 0.013 (7) | 0.012 (7) | 0.014 (6) | 0.002 (6) |
C1D | 0.040 (9) | 0.045 (8) | 0.011 (7) | 0.014 (7) | 0.013 (6) | 0.011 (6) |
C1C | 0.045 (9) | 0.047 (8) | 0.015 (6) | 0.015 (7) | 0.008 (6) | 0.005 (6) |
C1B | 0.049 (9) | 0.049 (8) | 0.015 (6) | 0.012 (7) | 0.009 (6) | 0.003 (6) |
C1A | 0.052 (9) | 0.046 (8) | 0.013 (6) | 0.011 (7) | 0.013 (6) | 0.002 (6) |
C19 | 0.051 (9) | 0.048 (8) | 0.016 (7) | 0.010 (7) | 0.012 (7) | −0.001 (6) |
Cl5 | 0.052 (3) | 0.090 (5) | 0.079 (4) | −0.011 (4) | −0.015 (3) | 0.016 (4) |
Cl6 | 0.089 (5) | 0.050 (3) | 0.097 (5) | −0.002 (3) | −0.030 (4) | −0.010 (3) |
C20 | 0.051 (13) | 0.037 (11) | 0.10 (2) | 0.004 (11) | −0.026 (14) | −0.001 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.334 (3) | C32—C33 | 1.380 (4) |
O1—H1 | 0.8402 | C32—H32 | 0.9500 |
O2—C1 | 1.210 (3) | C33—C34 | 1.383 (4) |
O3—C17 | 1.231 (2) | C33—H33 | 0.9500 |
O4—C7 | 1.373 (2) | C34—C35 | 1.376 (4) |
O4—H4 | 0.8400 | C34—H34 | 0.9500 |
N1—C17 | 1.341 (3) | C35—C36 | 1.392 (3) |
N1—C2 | 1.452 (2) | C35—H35 | 0.9500 |
N1—H1A | 0.8800 | C36—H36 | 0.9500 |
C1—C2 | 1.519 (3) | C11A—C16A | 1.3900 |
C2—C3 | 1.541 (3) | C11A—C12A | 1.3900 |
C2—H2 | 1.0000 | C16A—C15A | 1.3900 |
C3—C4 | 1.509 (2) | C16A—H16A | 0.9500 |
C3—H3A | 0.9900 | C15A—C14A | 1.3900 |
C3—H3B | 0.9900 | C15A—H15A | 0.9500 |
C4—C5 | 1.387 (3) | C14A—C13A | 1.3900 |
C4—C9 | 1.390 (3) | C14A—H14A | 0.9500 |
C5—C6 | 1.393 (3) | C13A—C12A | 1.3900 |
C5—H5 | 0.9500 | C13A—H13A | 0.9500 |
C6—C7 | 1.381 (3) | C12A—H12A | 0.9500 |
C6—H6 | 0.9500 | C21A—C22A | 1.3900 |
C7—C8 | 1.385 (3) | C21A—C26A | 1.3900 |
C8—C9 | 1.386 (3) | C22A—C23A | 1.3900 |
C8—H8 | 0.9500 | C22A—H22A | 0.9500 |
C9—H9 | 0.9500 | C23A—C24A | 1.3900 |
C10—C31A | 1.468 (17) | C23A—H23A | 0.9500 |
C10—C1D | 1.514 (12) | C24A—C25A | 1.3900 |
C10—C11A | 1.536 (9) | C24A—H24A | 0.9500 |
C10—C21 | 1.536 (5) | C25A—C26A | 1.3900 |
C10—C31 | 1.558 (4) | C25A—H25A | 0.9500 |
C10—C17 | 1.564 (3) | C26A—H26A | 0.9500 |
C10—C21A | 1.571 (19) | C31A—C32A | 1.3900 |
C10—C11 | 1.598 (3) | C31A—C36A | 1.3900 |
C11—C16 | 1.3900 | C32A—C33A | 1.3900 |
C11—C12 | 1.3900 | C32A—H32A | 0.9500 |
C16—C15 | 1.3900 | C33A—C34A | 1.3900 |
C16—H16 | 0.9500 | C33A—H33A | 0.9500 |
C15—C14 | 1.3900 | C34A—C35A | 1.3900 |
C15—H15 | 0.9500 | C34A—H34A | 0.9500 |
C14—C13 | 1.3900 | C35A—C36A | 1.3900 |
C14—H14 | 0.9500 | C35A—H35A | 0.9500 |
C13—C12 | 1.3900 | C36A—H36A | 0.9500 |
C13—H13 | 0.9500 | C18—C1D | 1.3900 |
C12—H12 | 0.9500 | C18—C19 | 1.3900 |
C21—C22 | 1.386 (4) | C18—H18 | 0.9500 |
C21—C26 | 1.400 (4) | C1D—C1C | 1.3900 |
C22—C23 | 1.393 (5) | C1C—C1B | 1.3900 |
C22—H22 | 0.9500 | C1C—H1C | 0.9500 |
C23—C24 | 1.374 (5) | C1B—C1A | 1.3900 |
C23—H23 | 0.9500 | C1B—H1B | 0.9500 |
C24—C25 | 1.379 (5) | C1A—C19 | 1.3900 |
C24—H24 | 0.9500 | C1A—H1AA | 0.9500 |
C25—C26 | 1.380 (5) | C19—H19 | 0.9500 |
C25—H25 | 0.9500 | Cl5—C20 | 1.74 (2) |
C26—H26 | 0.9500 | Cl6—C20 | 1.724 (19) |
C31—C36 | 1.389 (3) | C20—H20A | 0.9900 |
C31—C32 | 1.395 (4) | C20—H20B | 0.9900 |
| | | |
C1—O1—H1 | 109.5 | C33—C32—C31 | 121.6 (3) |
C7—O4—H4 | 109.5 | C33—C32—H32 | 119.2 |
C17—N1—C2 | 123.06 (17) | C31—C32—H32 | 119.2 |
C17—N1—H1A | 118.5 | C32—C33—C34 | 120.4 (2) |
C2—N1—H1A | 118.5 | C32—C33—H33 | 119.8 |
O2—C1—O1 | 124.5 (2) | C34—C33—H33 | 119.8 |
O2—C1—C2 | 123.6 (2) | C35—C34—C33 | 119.1 (3) |
O1—C1—C2 | 111.74 (18) | C35—C34—H34 | 120.5 |
N1—C2—C1 | 109.85 (16) | C33—C34—H34 | 120.5 |
N1—C2—C3 | 111.92 (16) | C34—C35—C36 | 120.4 (2) |
C1—C2—C3 | 105.32 (16) | C34—C35—H35 | 119.8 |
N1—C2—H2 | 109.9 | C36—C35—H35 | 119.8 |
C1—C2—H2 | 109.9 | C31—C36—C35 | 121.4 (2) |
C3—C2—H2 | 109.9 | C31—C36—H36 | 119.3 |
C4—C3—C2 | 114.29 (16) | C35—C36—H36 | 119.3 |
C4—C3—H3A | 108.7 | C16A—C11A—C12A | 120.0 |
C2—C3—H3A | 108.7 | C16A—C11A—C10 | 125.3 (9) |
C4—C3—H3B | 108.7 | C12A—C11A—C10 | 114.3 (9) |
C2—C3—H3B | 108.7 | C11A—C16A—C15A | 120.0 |
H3A—C3—H3B | 107.6 | C11A—C16A—H16A | 120.0 |
C5—C4—C9 | 118.13 (16) | C15A—C16A—H16A | 120.0 |
C5—C4—C3 | 120.29 (18) | C14A—C15A—C16A | 120.0 |
C9—C4—C3 | 121.56 (18) | C14A—C15A—H15A | 120.0 |
C4—C5—C6 | 121.26 (18) | C16A—C15A—H15A | 120.0 |
C4—C5—H5 | 119.4 | C15A—C14A—C13A | 120.0 |
C6—C5—H5 | 119.4 | C15A—C14A—H14A | 120.0 |
C7—C6—C5 | 119.39 (19) | C13A—C14A—H14A | 120.0 |
C7—C6—H6 | 120.3 | C14A—C13A—C12A | 120.0 |
C5—C6—H6 | 120.3 | C14A—C13A—H13A | 120.0 |
O4—C7—C6 | 121.59 (18) | C12A—C13A—H13A | 120.0 |
O4—C7—C8 | 118.01 (18) | C13A—C12A—C11A | 120.0 |
C6—C7—C8 | 120.39 (17) | C13A—C12A—H12A | 120.0 |
C7—C8—C9 | 119.49 (19) | C11A—C12A—H12A | 120.0 |
C7—C8—H8 | 120.3 | C22A—C21A—C26A | 120.0 |
C9—C8—H8 | 120.3 | C22A—C21A—C10 | 119 (2) |
C8—C9—C4 | 121.34 (18) | C26A—C21A—C10 | 121 (2) |
C8—C9—H9 | 119.3 | C21A—C22A—C23A | 120.0 |
C4—C9—H9 | 119.3 | C21A—C22A—H22A | 120.0 |
C31A—C10—C11A | 123.1 (11) | C23A—C22A—H22A | 120.0 |
C21—C10—C31 | 112.1 (3) | C24A—C23A—C22A | 120.0 |
C31A—C10—C17 | 105.0 (10) | C24A—C23A—H23A | 120.0 |
C1D—C10—C17 | 109.6 (10) | C22A—C23A—H23A | 120.0 |
C11A—C10—C17 | 105.1 (5) | C23A—C24A—C25A | 120.0 |
C21—C10—C17 | 110.3 (3) | C23A—C24A—H24A | 120.0 |
C31—C10—C17 | 106.4 (2) | C25A—C24A—H24A | 120.0 |
C31A—C10—C21A | 110.7 (18) | C24A—C25A—C26A | 120.0 |
C11A—C10—C21A | 100.9 (17) | C24A—C25A—H25A | 120.0 |
C17—C10—C21A | 111.9 (15) | C26A—C25A—H25A | 120.0 |
C21—C10—C11 | 112.9 (3) | C25A—C26A—C21A | 120.0 |
C31—C10—C11 | 103.6 (2) | C25A—C26A—H26A | 120.0 |
C17—C10—C11 | 111.19 (18) | C21A—C26A—H26A | 120.0 |
O3—C17—N1 | 122.29 (19) | C32A—C31A—C36A | 120.0 |
O3—C17—C10 | 121.36 (19) | C32A—C31A—C10 | 117.1 (14) |
N1—C17—C10 | 116.24 (17) | C36A—C31A—C10 | 122.9 (14) |
C16—C11—C12 | 120.0 | C31A—C32A—C33A | 120.0 |
C16—C11—C10 | 119.03 (18) | C31A—C32A—H32A | 120.0 |
C12—C11—C10 | 120.94 (18) | C33A—C32A—H32A | 120.0 |
C11—C16—C15 | 120.0 | C32A—C33A—C34A | 120.0 |
C11—C16—H16 | 120.0 | C32A—C33A—H33A | 120.0 |
C15—C16—H16 | 120.0 | C34A—C33A—H33A | 120.0 |
C14—C15—C16 | 120.0 | C35A—C34A—C33A | 120.0 |
C14—C15—H15 | 120.0 | C35A—C34A—H34A | 120.0 |
C16—C15—H15 | 120.0 | C33A—C34A—H34A | 120.0 |
C15—C14—C13 | 120.0 | C34A—C35A—C36A | 120.0 |
C15—C14—H14 | 120.0 | C34A—C35A—H35A | 120.0 |
C13—C14—H14 | 120.0 | C36A—C35A—H35A | 120.0 |
C14—C13—C12 | 120.0 | C35A—C36A—C31A | 120.0 |
C14—C13—H13 | 120.0 | C35A—C36A—H36A | 120.0 |
C12—C13—H13 | 120.0 | C31A—C36A—H36A | 120.0 |
C13—C12—C11 | 120.0 | C1D—C18—C19 | 120.0 |
C13—C12—H12 | 120.0 | C1D—C18—H18 | 120.0 |
C11—C12—H12 | 120.0 | C19—C18—H18 | 120.0 |
C22—C21—C26 | 117.9 (3) | C18—C1D—C1C | 120.0 |
C22—C21—C10 | 123.4 (4) | C18—C1D—C10 | 119.7 (14) |
C26—C21—C10 | 118.7 (4) | C1C—C1D—C10 | 119.7 (14) |
C21—C22—C23 | 120.7 (3) | C1B—C1C—C1D | 120.0 |
C21—C22—H22 | 119.7 | C1B—C1C—H1C | 120.0 |
C23—C22—H22 | 119.7 | C1D—C1C—H1C | 120.0 |
C24—C23—C22 | 120.4 (3) | C1C—C1B—C1A | 120.0 |
C24—C23—H23 | 119.8 | C1C—C1B—H1B | 120.0 |
C22—C23—H23 | 119.8 | C1A—C1B—H1B | 120.0 |
C23—C24—C25 | 119.8 (3) | C19—C1A—C1B | 120.0 |
C23—C24—H24 | 120.1 | C19—C1A—H1AA | 120.0 |
C25—C24—H24 | 120.1 | C1B—C1A—H1AA | 120.0 |
C24—C25—C26 | 120.0 (3) | C1A—C19—C18 | 120.0 |
C24—C25—H25 | 120.0 | C1A—C19—H19 | 120.0 |
C26—C25—H25 | 120.0 | C18—C19—H19 | 120.0 |
C25—C26—C21 | 121.2 (3) | Cl6—C20—Cl5 | 112.9 (14) |
C25—C26—H26 | 119.4 | Cl6—C20—H20A | 109.0 |
C21—C26—H26 | 119.4 | Cl5—C20—H20A | 109.0 |
C36—C31—C32 | 117.1 (2) | Cl6—C20—H20B | 109.0 |
C36—C31—C10 | 122.8 (3) | Cl5—C20—H20B | 109.0 |
C32—C31—C10 | 120.1 (3) | H20A—C20—H20B | 107.8 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.84 | 1.91 | 2.729 (2) | 166 |
C16Ab—H16Ab···O3 | 0.95 | 2.04 | 2.708 (10) | 126 |
O1—H1···O4ii | 0.84 | 1.89 | 2.700 (2) | 161 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x, y−1, z. |
N-Triphenylacetyl-
L-tyrosine chloroform sesquisolvate (V)
top
Crystal data top
C29H25NO4·1.5CHCl3 | F(000) = 1300 |
Mr = 630.55 | Dx = 1.407 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 10.00099 (16) Å | Cell parameters from 7060 reflections |
b = 9.33129 (13) Å | θ = 2.8–75.5° |
c = 31.8959 (5) Å | µ = 4.33 mm−1 |
β = 90.4958 (13)° | T = 130 K |
V = 2976.48 (8) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.02 × 0.02 mm |
Data collection top
Rigaku SuperNova Single Source diffractometer with an Atlas detector | 6149 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 4806 reflections with I > 2σ(I) |
Detector resolution: 10.5384 pixels mm-1 | Rint = 0.046 |
ω scans | θmax = 76.3°, θmin = 4.4° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | h = −12→12 |
Tmin = 0.773, Tmax = 1.000 | k = −11→11 |
20990 measured reflections | l = −39→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0672P)2 + 2.6801P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6149 reflections | Δρmax = 0.84 e Å−3 |
372 parameters | Δρmin = −0.84 e Å−3 |
0 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The diffraction data for all monocrystals were collected at 130 K
with an Oxford Diffraction SuperNova diffractometer using Cu Kα radiation
(λ = 1.54184 Å). The intensity data were collected and processed with
the use of CrysAlis PRO software (1.171.40.67a). The structures were
solved by
direct methods with the program SHELXT2018 (Sheldrick, 2015b) and
refined by full-matrix least-squares method on F2 with SHELXL2018
(Sheldrick, 2015a). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5998 (2) | 0.9027 (2) | 0.46371 (7) | 0.0463 (5) | |
H1 | 0.601302 | 0.962677 | 0.483333 | 0.070* | |
O2 | 0.3801 (2) | 0.9031 (2) | 0.47625 (6) | 0.0394 (5) | |
O3 | 0.3674 (2) | 0.9053 (2) | 0.36910 (7) | 0.0449 (5) | |
O4 | 0.5463 (2) | 0.1021 (2) | 0.35165 (7) | 0.0413 (5) | |
H4 | 0.484214 | 0.044147 | 0.356663 | 0.062* | |
N1 | 0.3431 (2) | 0.7112 (2) | 0.40825 (7) | 0.0301 (5) | |
H1A | 0.291906 | 0.639579 | 0.416128 | 0.036* | |
C1 | 0.4771 (3) | 0.8568 (3) | 0.45795 (9) | 0.0331 (6) | |
C2 | 0.4731 (3) | 0.7304 (3) | 0.42790 (8) | 0.0316 (5) | |
H2 | 0.541510 | 0.745176 | 0.405637 | 0.038* | |
C3 | 0.5103 (3) | 0.5967 (3) | 0.45362 (9) | 0.0370 (6) | |
H3A | 0.597385 | 0.613108 | 0.467836 | 0.044* | |
H3B | 0.442259 | 0.581654 | 0.475536 | 0.044* | |
C4 | 0.5197 (3) | 0.4633 (3) | 0.42706 (8) | 0.0339 (6) | |
C5 | 0.6186 (3) | 0.4493 (3) | 0.39726 (10) | 0.0397 (6) | |
H5 | 0.682056 | 0.524066 | 0.393959 | 0.048* | |
C6 | 0.6271 (3) | 0.3283 (3) | 0.37208 (10) | 0.0403 (6) | |
H6 | 0.694858 | 0.321024 | 0.351502 | 0.048* | |
C7 | 0.5353 (3) | 0.2179 (3) | 0.37729 (9) | 0.0324 (5) | |
C8 | 0.4369 (3) | 0.2292 (3) | 0.40749 (8) | 0.0333 (6) | |
H8 | 0.375020 | 0.153300 | 0.411435 | 0.040* | |
C9 | 0.4292 (3) | 0.3518 (3) | 0.43191 (9) | 0.0358 (6) | |
H9 | 0.360923 | 0.359684 | 0.452293 | 0.043* | |
C10 | 0.1607 (3) | 0.7723 (3) | 0.35860 (8) | 0.0268 (5) | |
C11 | 0.1290 (3) | 0.6107 (3) | 0.36165 (7) | 0.0268 (5) | |
C12 | 0.2152 (3) | 0.5126 (3) | 0.34268 (8) | 0.0305 (5) | |
H12 | 0.292339 | 0.546646 | 0.328622 | 0.037* | |
C13 | 0.1901 (3) | 0.3663 (3) | 0.34406 (8) | 0.0324 (6) | |
H13 | 0.248892 | 0.301274 | 0.330592 | 0.039* | |
C14 | 0.0790 (3) | 0.3150 (3) | 0.36510 (8) | 0.0341 (6) | |
H14 | 0.061542 | 0.215049 | 0.366187 | 0.041* | |
C15 | −0.0058 (3) | 0.4106 (3) | 0.38444 (9) | 0.0367 (6) | |
H15 | −0.081616 | 0.375530 | 0.398984 | 0.044* | |
C16 | 0.0178 (3) | 0.5579 (3) | 0.38298 (8) | 0.0322 (5) | |
H16 | −0.041531 | 0.622201 | 0.396466 | 0.039* | |
C17 | 0.3000 (3) | 0.8006 (3) | 0.37836 (8) | 0.0282 (5) | |
C21 | 0.1579 (3) | 0.8235 (3) | 0.31226 (8) | 0.0291 (5) | |
C26 | 0.1170 (3) | 0.7361 (3) | 0.27944 (8) | 0.0336 (6) | |
H26 | 0.095988 | 0.638519 | 0.284794 | 0.040* | |
C25 | 0.1060 (3) | 0.7894 (3) | 0.23847 (9) | 0.0405 (6) | |
H25 | 0.077869 | 0.727710 | 0.216400 | 0.049* | |
C24 | 0.1357 (3) | 0.9306 (3) | 0.22998 (9) | 0.0425 (7) | |
H24 | 0.128782 | 0.966498 | 0.202176 | 0.051* | |
C23 | 0.1759 (3) | 1.0197 (3) | 0.26266 (10) | 0.0421 (7) | |
H23 | 0.196655 | 1.117189 | 0.257109 | 0.050* | |
C22 | 0.1860 (3) | 0.9676 (3) | 0.30334 (9) | 0.0368 (6) | |
H22 | 0.212161 | 1.030244 | 0.325400 | 0.044* | |
C31 | 0.0595 (3) | 0.8657 (3) | 0.38274 (8) | 0.0300 (5) | |
C32 | −0.0672 (3) | 0.8882 (3) | 0.36508 (10) | 0.0399 (6) | |
H32 | −0.089783 | 0.843632 | 0.339185 | 0.048* | |
C33 | −0.1601 (3) | 0.9741 (4) | 0.38467 (11) | 0.0473 (7) | |
H33 | −0.245923 | 0.987401 | 0.372282 | 0.057* | |
C34 | −0.1290 (3) | 1.0410 (3) | 0.42226 (10) | 0.0444 (7) | |
H34 | −0.192696 | 1.100561 | 0.435671 | 0.053* | |
C35 | −0.0040 (4) | 1.0199 (3) | 0.44000 (10) | 0.0437 (7) | |
H35 | 0.018509 | 1.065962 | 0.465659 | 0.052* | |
C36 | 0.0896 (3) | 0.9314 (3) | 0.42055 (9) | 0.0360 (6) | |
H36 | 0.174545 | 0.916196 | 0.433375 | 0.043* | |
Cl1 | 0.71493 (10) | 0.92450 (10) | 0.26976 (3) | 0.0571 (2) | |
Cl2 | 0.58506 (12) | 0.69569 (12) | 0.31441 (3) | 0.0687 (3) | |
Cl3 | 0.49741 (10) | 0.77083 (14) | 0.23118 (3) | 0.0708 (3) | |
C40 | 0.5626 (4) | 0.8377 (4) | 0.27843 (11) | 0.0516 (8) | |
H40 | 0.497784 | 0.908009 | 0.290376 | 0.062* | |
Cl4 | 0.12260 (18) | 0.5933 (2) | 0.49947 (5) | 0.1123 (5) | |
C41 | 0.0573 (10) | 0.4262 (12) | 0.4899 (3) | 0.081 (3) | 0.5 |
H41 | 0.070867 | 0.404577 | 0.460795 | 0.097* | 0.5 |
Cl5 | 0.1347 (2) | 0.3002 (2) | 0.51810 (5) | 0.0620 (5) | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0349 (10) | 0.0471 (12) | 0.0570 (13) | −0.0091 (9) | −0.0027 (9) | −0.0248 (10) |
O2 | 0.0352 (10) | 0.0398 (11) | 0.0432 (11) | −0.0020 (9) | −0.0058 (8) | −0.0130 (9) |
O3 | 0.0416 (11) | 0.0326 (10) | 0.0602 (13) | −0.0119 (9) | −0.0124 (10) | 0.0107 (9) |
O4 | 0.0419 (11) | 0.0291 (10) | 0.0531 (12) | −0.0047 (8) | 0.0088 (9) | −0.0094 (9) |
N1 | 0.0346 (11) | 0.0241 (10) | 0.0315 (11) | −0.0045 (9) | −0.0084 (9) | −0.0009 (8) |
C1 | 0.0357 (14) | 0.0280 (12) | 0.0356 (13) | −0.0017 (11) | −0.0084 (11) | −0.0027 (11) |
C2 | 0.0366 (14) | 0.0268 (12) | 0.0311 (12) | −0.0001 (11) | −0.0082 (10) | −0.0032 (10) |
C3 | 0.0464 (16) | 0.0293 (13) | 0.0350 (14) | 0.0042 (12) | −0.0136 (12) | −0.0024 (11) |
C4 | 0.0399 (14) | 0.0273 (12) | 0.0343 (13) | 0.0030 (11) | −0.0144 (11) | 0.0010 (11) |
C5 | 0.0361 (14) | 0.0257 (13) | 0.0570 (18) | −0.0046 (11) | −0.0069 (13) | 0.0025 (12) |
C6 | 0.0339 (14) | 0.0330 (14) | 0.0540 (17) | −0.0017 (12) | 0.0053 (12) | −0.0021 (13) |
C7 | 0.0331 (13) | 0.0240 (12) | 0.0399 (14) | 0.0020 (10) | −0.0044 (11) | −0.0002 (10) |
C8 | 0.0368 (14) | 0.0272 (12) | 0.0360 (14) | −0.0001 (11) | −0.0024 (11) | 0.0023 (11) |
C9 | 0.0416 (15) | 0.0326 (13) | 0.0332 (13) | 0.0019 (12) | −0.0026 (11) | 0.0003 (11) |
C10 | 0.0303 (12) | 0.0230 (11) | 0.0271 (12) | −0.0020 (9) | −0.0038 (9) | −0.0012 (9) |
C11 | 0.0319 (12) | 0.0237 (11) | 0.0247 (11) | −0.0045 (10) | −0.0075 (9) | 0.0001 (9) |
C12 | 0.0331 (13) | 0.0286 (12) | 0.0298 (12) | −0.0033 (10) | −0.0025 (10) | −0.0007 (10) |
C13 | 0.0399 (14) | 0.0257 (12) | 0.0315 (13) | −0.0007 (11) | −0.0072 (11) | −0.0025 (10) |
C14 | 0.0446 (15) | 0.0231 (12) | 0.0344 (13) | −0.0075 (11) | −0.0072 (11) | 0.0033 (10) |
C15 | 0.0381 (14) | 0.0349 (14) | 0.0371 (14) | −0.0099 (12) | 0.0004 (11) | 0.0047 (12) |
C16 | 0.0365 (14) | 0.0292 (13) | 0.0308 (13) | −0.0038 (11) | −0.0012 (10) | 0.0009 (10) |
C17 | 0.0321 (13) | 0.0216 (11) | 0.0308 (12) | −0.0013 (10) | −0.0023 (10) | −0.0022 (9) |
C21 | 0.0302 (12) | 0.0270 (12) | 0.0299 (12) | 0.0003 (10) | −0.0030 (10) | 0.0034 (10) |
C26 | 0.0412 (14) | 0.0284 (13) | 0.0312 (13) | −0.0008 (11) | −0.0056 (11) | 0.0011 (10) |
C25 | 0.0484 (17) | 0.0420 (15) | 0.0310 (14) | 0.0041 (13) | −0.0072 (12) | 0.0006 (12) |
C24 | 0.0485 (17) | 0.0459 (16) | 0.0330 (14) | 0.0069 (14) | −0.0015 (12) | 0.0097 (13) |
C23 | 0.0498 (17) | 0.0326 (14) | 0.0438 (16) | 0.0026 (13) | 0.0011 (13) | 0.0108 (12) |
C22 | 0.0427 (15) | 0.0288 (13) | 0.0387 (15) | −0.0003 (11) | −0.0026 (12) | 0.0017 (11) |
C31 | 0.0330 (13) | 0.0241 (11) | 0.0328 (13) | −0.0016 (10) | −0.0001 (10) | 0.0020 (10) |
C32 | 0.0364 (15) | 0.0402 (15) | 0.0430 (15) | 0.0022 (12) | −0.0037 (12) | −0.0058 (13) |
C33 | 0.0344 (15) | 0.0461 (17) | 0.062 (2) | 0.0054 (13) | 0.0015 (14) | −0.0003 (15) |
C34 | 0.0485 (17) | 0.0319 (14) | 0.0531 (18) | 0.0039 (13) | 0.0132 (14) | 0.0002 (13) |
C35 | 0.0596 (19) | 0.0354 (15) | 0.0364 (15) | 0.0048 (14) | 0.0047 (13) | −0.0039 (12) |
C36 | 0.0428 (15) | 0.0311 (13) | 0.0340 (14) | 0.0026 (12) | −0.0024 (11) | −0.0010 (11) |
Cl1 | 0.0670 (5) | 0.0562 (5) | 0.0481 (4) | −0.0089 (4) | −0.0007 (4) | −0.0055 (4) |
Cl2 | 0.0845 (7) | 0.0692 (6) | 0.0526 (5) | 0.0086 (5) | 0.0197 (5) | 0.0112 (4) |
Cl3 | 0.0555 (5) | 0.0964 (8) | 0.0604 (5) | −0.0034 (5) | −0.0132 (4) | −0.0104 (5) |
C40 | 0.0529 (19) | 0.056 (2) | 0.0462 (18) | 0.0104 (16) | 0.0047 (14) | −0.0040 (15) |
Cl4 | 0.1073 (11) | 0.1421 (15) | 0.0876 (9) | 0.0205 (10) | 0.0117 (8) | 0.0003 (9) |
C41 | 0.091 (7) | 0.102 (7) | 0.050 (4) | 0.028 (6) | 0.030 (4) | 0.017 (5) |
Cl5 | 0.0652 (11) | 0.0747 (12) | 0.0461 (9) | −0.0163 (9) | 0.0030 (7) | −0.0053 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.311 (3) | C14—H14 | 0.9500 |
O1—H1 | 0.8400 | C15—C16 | 1.395 (4) |
O2—C1 | 1.216 (4) | C15—H15 | 0.9500 |
O3—C17 | 1.224 (3) | C16—H16 | 0.9500 |
O4—C7 | 1.359 (3) | C21—C26 | 1.386 (4) |
O4—H4 | 0.8400 | C21—C22 | 1.404 (4) |
N1—C17 | 1.335 (3) | C26—C25 | 1.401 (4) |
N1—C2 | 1.449 (3) | C26—H26 | 0.9500 |
N1—H1A | 0.8800 | C25—C24 | 1.378 (4) |
C1—C2 | 1.520 (4) | C25—H25 | 0.9500 |
C2—C3 | 1.538 (4) | C24—C23 | 1.390 (5) |
C2—H2 | 1.0000 | C24—H24 | 0.9500 |
C3—C4 | 1.509 (4) | C23—C22 | 1.388 (4) |
C3—H3A | 0.9900 | C23—H23 | 0.9500 |
C3—H3B | 0.9900 | C22—H22 | 0.9500 |
C4—C5 | 1.383 (4) | C31—C36 | 1.384 (4) |
C4—C9 | 1.388 (4) | C31—C32 | 1.398 (4) |
C5—C6 | 1.389 (4) | C32—C33 | 1.380 (4) |
C5—H5 | 0.9500 | C32—H32 | 0.9500 |
C6—C7 | 1.391 (4) | C33—C34 | 1.385 (5) |
C6—H6 | 0.9500 | C33—H33 | 0.9500 |
C7—C8 | 1.387 (4) | C34—C35 | 1.382 (5) |
C8—C9 | 1.386 (4) | C34—H34 | 0.9500 |
C8—H8 | 0.9500 | C35—C36 | 1.398 (4) |
C9—H9 | 0.9500 | C35—H35 | 0.9500 |
C10—C11 | 1.544 (3) | C36—H36 | 0.9500 |
C10—C31 | 1.546 (4) | Cl1—C40 | 1.750 (4) |
C10—C17 | 1.547 (3) | Cl2—C40 | 1.766 (4) |
C10—C21 | 1.553 (3) | Cl3—C40 | 1.751 (4) |
C11—C16 | 1.398 (4) | C40—H40 | 1.0000 |
C11—C12 | 1.399 (4) | Cl4—C41 | 1.717 (12) |
C12—C13 | 1.389 (4) | Cl4—C41i | 1.843 (10) |
C12—H12 | 0.9500 | C41—Cl5 | 1.667 (9) |
C13—C14 | 1.388 (4) | C41—C41i | 1.908 (18) |
C13—H13 | 0.9500 | C41—H41 | 0.9600 |
C14—C15 | 1.380 (4) | | |
| | | |
C1—O1—H1 | 109.5 | C15—C16—C11 | 120.0 (3) |
C7—O4—H4 | 109.5 | C15—C16—H16 | 120.0 |
C17—N1—C2 | 121.0 (2) | C11—C16—H16 | 120.0 |
C17—N1—H1A | 119.5 | O3—C17—N1 | 119.7 (2) |
C2—N1—H1A | 119.5 | O3—C17—C10 | 122.2 (2) |
O2—C1—O1 | 124.5 (2) | N1—C17—C10 | 117.9 (2) |
O2—C1—C2 | 124.2 (2) | C26—C21—C22 | 118.0 (2) |
O1—C1—C2 | 111.2 (2) | C26—C21—C10 | 122.7 (2) |
N1—C2—C1 | 112.8 (2) | C22—C21—C10 | 119.0 (2) |
N1—C2—C3 | 110.0 (2) | C21—C26—C25 | 121.0 (3) |
C1—C2—C3 | 106.8 (2) | C21—C26—H26 | 119.5 |
N1—C2—H2 | 109.1 | C25—C26—H26 | 119.5 |
C1—C2—H2 | 109.1 | C24—C25—C26 | 120.5 (3) |
C3—C2—H2 | 109.1 | C24—C25—H25 | 119.8 |
C4—C3—C2 | 112.7 (2) | C26—C25—H25 | 119.8 |
C4—C3—H3A | 109.1 | C25—C24—C23 | 119.1 (3) |
C2—C3—H3A | 109.1 | C25—C24—H24 | 120.5 |
C4—C3—H3B | 109.1 | C23—C24—H24 | 120.5 |
C2—C3—H3B | 109.1 | C22—C23—C24 | 120.6 (3) |
H3A—C3—H3B | 107.8 | C22—C23—H23 | 119.7 |
C5—C4—C9 | 118.4 (3) | C24—C23—H23 | 119.7 |
C5—C4—C3 | 120.8 (3) | C23—C22—C21 | 120.8 (3) |
C9—C4—C3 | 120.8 (3) | C23—C22—H22 | 119.6 |
C4—C5—C6 | 121.5 (3) | C21—C22—H22 | 119.6 |
C4—C5—H5 | 119.3 | C36—C31—C32 | 118.3 (3) |
C6—C5—H5 | 119.3 | C36—C31—C10 | 123.0 (2) |
C5—C6—C7 | 119.3 (3) | C32—C31—C10 | 118.6 (2) |
C5—C6—H6 | 120.4 | C33—C32—C31 | 121.0 (3) |
C7—C6—H6 | 120.4 | C33—C32—H32 | 119.5 |
O4—C7—C8 | 122.7 (2) | C31—C32—H32 | 119.5 |
O4—C7—C6 | 117.3 (3) | C32—C33—C34 | 120.5 (3) |
C8—C7—C6 | 119.9 (3) | C32—C33—H33 | 119.8 |
C9—C8—C7 | 119.8 (3) | C34—C33—H33 | 119.8 |
C9—C8—H8 | 120.1 | C35—C34—C33 | 119.1 (3) |
C7—C8—H8 | 120.1 | C35—C34—H34 | 120.5 |
C8—C9—C4 | 121.1 (3) | C33—C34—H34 | 120.5 |
C8—C9—H9 | 119.5 | C34—C35—C36 | 120.7 (3) |
C4—C9—H9 | 119.5 | C34—C35—H35 | 119.7 |
C11—C10—C31 | 112.5 (2) | C36—C35—H35 | 119.7 |
C11—C10—C17 | 109.0 (2) | C31—C36—C35 | 120.4 (3) |
C31—C10—C17 | 107.0 (2) | C31—C36—H36 | 119.8 |
C11—C10—C21 | 111.0 (2) | C35—C36—H36 | 119.8 |
C31—C10—C21 | 107.1 (2) | Cl1—C40—Cl3 | 110.30 (19) |
C17—C10—C21 | 110.1 (2) | Cl1—C40—Cl2 | 110.1 (2) |
C16—C11—C12 | 118.4 (2) | Cl3—C40—Cl2 | 109.7 (2) |
C16—C11—C10 | 122.7 (2) | Cl1—C40—H40 | 108.9 |
C12—C11—C10 | 118.9 (2) | Cl3—C40—H40 | 108.9 |
C13—C12—C11 | 121.1 (3) | Cl2—C40—H40 | 108.9 |
C13—C12—H12 | 119.4 | C41—Cl4—C41i | 64.7 (5) |
C11—C12—H12 | 119.4 | Cl5—C41—Cl4 | 111.7 (6) |
C14—C13—C12 | 120.0 (3) | Cl5—C41—Cl4i | 106.3 (5) |
C14—C13—H13 | 120.0 | Cl4—C41—Cl4i | 115.3 (5) |
C12—C13—H13 | 120.0 | Cl5—C41—C41i | 127.1 (7) |
C15—C14—C13 | 119.4 (2) | Cl4—C41—C41i | 60.8 (6) |
C15—C14—H14 | 120.3 | Cl4i—C41—C41i | 54.5 (5) |
C13—C14—H14 | 120.3 | Cl5—C41—H41 | 107.7 |
C14—C15—C16 | 121.1 (3) | Cl4—C41—H41 | 107.8 |
C14—C15—H15 | 119.5 | Cl4i—C41—H41 | 107.7 |
C16—C15—H15 | 119.5 | C41i—C41—H41 | 124.7 |
| | | |
C17—N1—C2—C1 | 73.3 (3) | C11—C10—C17—O3 | 156.7 (3) |
C17—N1—C2—C3 | −167.6 (2) | C31—C10—C17—O3 | −81.4 (3) |
O2—C1—C2—N1 | 26.5 (4) | C21—C10—C17—O3 | 34.7 (3) |
O1—C1—C2—N1 | −157.8 (2) | C11—C10—C17—N1 | −27.3 (3) |
O2—C1—C2—C3 | −94.4 (3) | C31—C10—C17—N1 | 94.6 (3) |
O1—C1—C2—C3 | 81.2 (3) | C21—C10—C17—N1 | −149.3 (2) |
N1—C2—C3—C4 | 61.2 (3) | C11—C10—C21—C26 | 6.7 (3) |
C1—C2—C3—C4 | −176.1 (2) | C31—C10—C21—C26 | −116.4 (3) |
C2—C3—C4—C5 | 66.5 (3) | C17—C10—C21—C26 | 127.5 (3) |
C2—C3—C4—C9 | −113.4 (3) | C11—C10—C21—C22 | −179.3 (2) |
C9—C4—C5—C6 | 1.1 (4) | C31—C10—C21—C22 | 57.5 (3) |
C3—C4—C5—C6 | −178.9 (3) | C17—C10—C21—C22 | −58.5 (3) |
C4—C5—C6—C7 | −0.9 (5) | C22—C21—C26—C25 | 1.0 (4) |
C5—C6—C7—O4 | 179.3 (3) | C10—C21—C26—C25 | 175.0 (3) |
C5—C6—C7—C8 | −0.2 (4) | C21—C26—C25—C24 | −0.1 (5) |
O4—C7—C8—C9 | −178.4 (3) | C26—C25—C24—C23 | −0.4 (5) |
C6—C7—C8—C9 | 1.1 (4) | C25—C24—C23—C22 | −0.1 (5) |
C7—C8—C9—C4 | −0.9 (4) | C24—C23—C22—C21 | 1.0 (5) |
C5—C4—C9—C8 | −0.2 (4) | C26—C21—C22—C23 | −1.5 (4) |
C3—C4—C9—C8 | 179.7 (2) | C10—C21—C22—C23 | −175.7 (3) |
C31—C10—C11—C16 | 1.9 (3) | C11—C10—C31—C36 | 105.9 (3) |
C17—C10—C11—C16 | 120.4 (3) | C17—C10—C31—C36 | −13.8 (3) |
C21—C10—C11—C16 | −118.1 (3) | C21—C10—C31—C36 | −131.9 (3) |
C31—C10—C11—C12 | −177.5 (2) | C11—C10—C31—C32 | −75.9 (3) |
C17—C10—C11—C12 | −59.0 (3) | C17—C10—C31—C32 | 164.4 (2) |
C21—C10—C11—C12 | 62.5 (3) | C21—C10—C31—C32 | 46.3 (3) |
C16—C11—C12—C13 | 1.4 (4) | C36—C31—C32—C33 | 0.2 (4) |
C10—C11—C12—C13 | −179.1 (2) | C10—C31—C32—C33 | −178.0 (3) |
C11—C12—C13—C14 | −1.1 (4) | C31—C32—C33—C34 | 0.5 (5) |
C12—C13—C14—C15 | 0.2 (4) | C32—C33—C34—C35 | −0.4 (5) |
C13—C14—C15—C16 | 0.4 (4) | C33—C34—C35—C36 | −0.5 (5) |
C14—C15—C16—C11 | 0.0 (4) | C32—C31—C36—C35 | −1.1 (4) |
C12—C11—C16—C15 | −0.9 (4) | C10—C31—C36—C35 | 177.1 (3) |
C10—C11—C16—C15 | 179.7 (2) | C34—C35—C36—C31 | 1.3 (5) |
C2—N1—C17—O3 | −4.4 (4) | C41i—Cl4—C41—Cl5 | −121.5 (7) |
C2—N1—C17—C10 | 179.5 (2) | C41i—Cl4—C41—Cl4i | 0.000 (1) |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2ii | 0.84 | 1.81 | 2.643 (3) | 175 |
O4—H4···O3iii | 0.84 | 1.79 | 2.628 (3) | 173 |
C22—H22···O3 | 0.95 | 2.38 | 2.822 (4) | 108 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z. |
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