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The absolute configuration has been established of the enantiopure anti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C30H19O4-·CH2Cl2. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [R22(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoretical versus experimental circular dichroism spectra.
Supporting information
CCDC reference: 966795
Data collection: RAPID-AUTO (Rigaku, 2010); cell refinement: RAPID-AUTO (Rigaku, 2010); data reduction: RAPID-AUTO (Rigaku, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
(
S)-2-(Hydroxymethyl)pyrrolidin-1-ium
5-carboxyheptacyclo[8.6.6.6
2,9.0
3,8.0
11,16.0
17,22.0
23,28]octacosa-2,4,6,8,11 (16),12,14,17 (22),18,20,23 (28),24,26-tridecaene-13-carboxylate dichloromethane monosolvate
top
Crystal data top
C5H12NO+·C30H19O4−·CH2Cl2 | F(000) = 660.00 |
Mr = 630.57 | Dx = 1.353 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: P 2yb | Cell parameters from 11621 reflections |
a = 11.4579 (2) Å | θ = 3.2–68.2° |
b = 9.83146 (18) Å | µ = 2.25 mm−1 |
c = 13.8027 (3) Å | T = 123 K |
β = 95.6581 (10)° | Platelet, colourless |
V = 1547.26 (5) Å3 | 0.80 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4490 reflections with F2 > 2σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.067 |
ω scans | θmax = 68.2° |
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983) | h = −13→13 |
Tmin = 0.654, Tmax = 0.798 | k = −11→11 |
17245 measured reflections | l = −16→15 |
5117 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.8448P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5117 reflections | Δρmax = 0.27 e Å−3 |
413 parameters | Δρmin = −0.41 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 2125 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.00 (2) |
Secondary atom site location: difference Fourier map | |
Special details top
Refinement. Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.38528 (10) | 0.53288 (15) | 0.42094 (8) | 0.0555 (4) | |
Cl2 | 0.38727 (10) | 0.70849 (13) | 0.59280 (8) | 0.0498 (3) | |
O1 | 0.0495 (2) | 0.4902 (3) | 0.32584 (15) | 0.0272 (6) | |
O2 | −0.1128 (3) | 0.3644 (3) | 0.31536 (17) | 0.0306 (6) | |
O3 | 0.1828 (3) | −0.2102 (3) | 0.37657 (16) | 0.0321 (6) | |
O4 | 0.1568 (3) | −0.3293 (3) | 0.23795 (17) | 0.0275 (6) | |
O5 | 0.0631 (3) | 0.4727 (4) | 0.52146 (19) | 0.0403 (8) | |
N1 | −0.1817 (3) | 0.4939 (4) | 0.4732 (3) | 0.0271 (7) | |
C1 | −0.0166 (3) | 0.3973 (4) | 0.2857 (3) | 0.0236 (8) | |
C2 | 0.0226 (3) | 0.3242 (4) | 0.1990 (3) | 0.0235 (8) | |
C3 | 0.1306 (3) | 0.3533 (4) | 0.1641 (3) | 0.0227 (8) | |
C4 | 0.1642 (3) | 0.2875 (4) | 0.0815 (3) | 0.0227 (8) | |
C5 | 0.2781 (3) | 0.3211 (4) | 0.0384 (3) | 0.0221 (8) | |
C6 | 0.2482 (3) | 0.3403 (4) | −0.0701 (3) | 0.0241 (8) | |
C7 | 0.2921 (4) | 0.4484 (4) | −0.1206 (3) | 0.0276 (8) | |
C8 | 0.2607 (4) | 0.4605 (5) | −0.2208 (3) | 0.0326 (9) | |
C9 | 0.1867 (4) | 0.3664 (5) | −0.2687 (3) | 0.0331 (9) | |
C10 | 0.1436 (3) | 0.2571 (5) | −0.2189 (3) | 0.0286 (9) | |
C11 | 0.1736 (3) | 0.2445 (4) | −0.1188 (3) | 0.0223 (8) | |
C12 | 0.1288 (3) | 0.1298 (4) | −0.0587 (3) | 0.0232 (8) | |
C13 | 0.0887 (3) | 0.1915 (4) | 0.0328 (3) | 0.0212 (7) | |
C14 | −0.0175 (3) | 0.1608 (4) | 0.0687 (3) | 0.0258 (8) | |
C15 | −0.0498 (3) | 0.2259 (4) | 0.1514 (3) | 0.0239 (8) | |
C16 | 0.3764 (3) | 0.2049 (4) | 0.0596 (3) | 0.0230 (8) | |
C17 | 0.4136 (3) | 0.1407 (4) | −0.0327 (3) | 0.0242 (8) | |
C18 | 0.5172 (3) | 0.1742 (5) | −0.0717 (3) | 0.0290 (9) | |
C19 | 0.5465 (3) | 0.1077 (5) | −0.1549 (3) | 0.0311 (9) | |
C20 | 0.4735 (3) | 0.0080 (5) | −0.1985 (3) | 0.0306 (9) | |
C21 | 0.3689 (3) | −0.0247 (4) | −0.1610 (3) | 0.0285 (9) | |
C22 | 0.3386 (3) | 0.0427 (4) | −0.0779 (3) | 0.0234 (8) | |
C23 | 0.2247 (3) | 0.0140 (4) | −0.0331 (2) | 0.0218 (7) | |
C24 | 0.2563 (3) | −0.0025 (4) | 0.0761 (3) | 0.0216 (8) | |
C25 | 0.2111 (3) | −0.1057 (4) | 0.1292 (3) | 0.0229 (8) | |
C26 | 0.2430 (3) | −0.1141 (4) | 0.2300 (3) | 0.0228 (8) | |
C27 | 0.3226 (3) | −0.0213 (4) | 0.2752 (3) | 0.0264 (8) | |
C28 | 0.3681 (3) | 0.0807 (4) | 0.2213 (3) | 0.0261 (8) | |
C29 | 0.3342 (3) | 0.0923 (4) | 0.1218 (3) | 0.0226 (8) | |
C30 | 0.1919 (3) | −0.2218 (4) | 0.2890 (3) | 0.0250 (8) | |
C31 | 0.3220 (6) | 0.5753 (7) | 0.5259 (4) | 0.0719 (18) | |
C32 | −0.1955 (4) | 0.7025 (5) | 0.5548 (3) | 0.0379 (9) | |
C33 | −0.3099 (4) | 0.6868 (5) | 0.4895 (4) | 0.0428 (11) | |
C34 | −0.3038 (4) | 0.5455 (5) | 0.4447 (3) | 0.0369 (10) | |
C35 | −0.1099 (4) | 0.6161 (4) | 0.5055 (3) | 0.0286 (8) | |
C36 | −0.0007 (4) | 0.5733 (5) | 0.5676 (3) | 0.0359 (10) | |
H1NA | −0.182 (4) | 0.431 (5) | 0.529 (4) | 0.053 (14)* | |
H1NB | −0.149 (4) | 0.449 (5) | 0.414 (4) | 0.049 (13)* | |
H3 | 0.1815 | 0.4183 | 0.1968 | 0.0272* | |
H5 | 0.3095 | 0.4087 | 0.0671 | 0.0265* | |
H5O | 0.066 (5) | 0.501 (7) | 0.464 (4) | 0.076 (19)* | |
H7 | 0.3427 | 0.5134 | −0.0874 | 0.0331* | |
H8 | 0.2905 | 0.5337 | −0.2559 | 0.0391* | |
H9 | 0.1649 | 0.3763 | −0.3366 | 0.0398* | |
H10 | 0.0941 | 0.1915 | −0.2528 | 0.0343* | |
H12 | 0.0594 | 0.0876 | −0.0969 | 0.0278* | |
H14 | −0.0682 | 0.0950 | 0.0365 | 0.0310* | |
H15 | −0.1220 | 0.2032 | 0.1757 | 0.0287* | |
H16 | 0.4471 | 0.2474 | 0.0958 | 0.0275* | |
H18 | 0.5676 | 0.2420 | −0.0417 | 0.0348* | |
H19 | 0.6170 | 0.1306 | −0.1819 | 0.0373* | |
H20 | 0.4952 | −0.0383 | −0.2545 | 0.0368* | |
H21 | 0.3185 | −0.0922 | −0.1914 | 0.0342* | |
H23 | 0.1922 | −0.0743 | −0.0596 | 0.0261* | |
H25 | 0.1588 | −0.1706 | 0.0977 | 0.0275* | |
H27 | 0.3455 | −0.0281 | 0.3431 | 0.0317* | |
H28 | 0.4228 | 0.1434 | 0.2522 | 0.0314* | |
H31A | 0.2387 | 0.5988 | 0.5075 | 0.0863* | |
H31B | 0.3234 | 0.4939 | 0.5682 | 0.0863* | |
H32A | −0.1700 | 0.7988 | 0.5584 | 0.0455* | |
H32B | −0.2038 | 0.6691 | 0.6214 | 0.0455* | |
H33A | −0.3166 | 0.7575 | 0.4382 | 0.0514* | |
H33B | −0.3781 | 0.6941 | 0.5280 | 0.0514* | |
H34A | −0.3625 | 0.4844 | 0.4700 | 0.0442* | |
H34B | −0.3195 | 0.5504 | 0.3730 | 0.0442* | |
H35 | −0.0870 | 0.6653 | 0.4469 | 0.0344* | |
H36A | 0.0500 | 0.6538 | 0.5819 | 0.0430* | |
H36B | −0.0227 | 0.5372 | 0.6302 | 0.0430* | |
H4O | 0.129 (5) | −0.385 (5) | 0.274 (4) | 0.051 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0492 (6) | 0.0680 (9) | 0.0505 (7) | 0.0079 (6) | 0.0107 (5) | −0.0041 (6) |
Cl2 | 0.0527 (6) | 0.0477 (7) | 0.0473 (6) | −0.0038 (6) | −0.0028 (5) | 0.0032 (6) |
O1 | 0.0375 (14) | 0.0261 (15) | 0.0182 (11) | −0.0059 (12) | 0.0040 (10) | −0.0001 (11) |
O2 | 0.0326 (14) | 0.0301 (16) | 0.0309 (13) | −0.0047 (12) | 0.0116 (11) | −0.0060 (12) |
O3 | 0.0519 (16) | 0.0267 (15) | 0.0187 (12) | 0.0004 (13) | 0.0081 (11) | −0.0007 (11) |
O4 | 0.0390 (14) | 0.0216 (15) | 0.0231 (12) | −0.0039 (11) | 0.0084 (11) | 0.0013 (11) |
O5 | 0.0475 (17) | 0.053 (2) | 0.0192 (13) | 0.0162 (15) | −0.0013 (12) | −0.0010 (13) |
N1 | 0.0344 (16) | 0.0256 (18) | 0.0211 (14) | −0.0010 (14) | 0.0024 (12) | −0.0027 (13) |
C1 | 0.0290 (18) | 0.024 (2) | 0.0178 (15) | 0.0022 (15) | 0.0014 (13) | 0.0003 (15) |
C2 | 0.0302 (18) | 0.021 (2) | 0.0190 (16) | 0.0030 (15) | 0.0020 (13) | 0.0028 (14) |
C3 | 0.0297 (18) | 0.0197 (19) | 0.0185 (16) | 0.0004 (15) | 0.0015 (13) | −0.0010 (14) |
C4 | 0.0238 (17) | 0.0237 (19) | 0.0198 (16) | 0.0027 (15) | −0.0009 (13) | 0.0038 (15) |
C5 | 0.0268 (17) | 0.0190 (19) | 0.0204 (16) | −0.0013 (14) | 0.0017 (13) | −0.0002 (14) |
C6 | 0.0287 (18) | 0.025 (2) | 0.0182 (16) | 0.0040 (16) | 0.0006 (13) | 0.0025 (15) |
C7 | 0.0287 (18) | 0.028 (3) | 0.0272 (18) | −0.0010 (16) | 0.0064 (14) | 0.0021 (15) |
C8 | 0.044 (3) | 0.029 (3) | 0.0267 (19) | 0.0010 (18) | 0.0092 (16) | 0.0063 (16) |
C9 | 0.044 (3) | 0.035 (3) | 0.0202 (18) | 0.0070 (19) | 0.0011 (15) | 0.0076 (17) |
C10 | 0.0283 (18) | 0.038 (3) | 0.0192 (16) | 0.0041 (16) | −0.0002 (14) | −0.0022 (15) |
C11 | 0.0189 (16) | 0.027 (2) | 0.0204 (16) | 0.0030 (14) | 0.0008 (12) | 0.0017 (14) |
C12 | 0.0241 (17) | 0.027 (2) | 0.0179 (16) | −0.0023 (15) | −0.0010 (13) | −0.0002 (15) |
C13 | 0.0217 (16) | 0.0226 (19) | 0.0184 (15) | 0.0012 (15) | −0.0021 (12) | −0.0007 (15) |
C14 | 0.0292 (18) | 0.024 (2) | 0.0234 (16) | −0.0006 (16) | −0.0015 (14) | −0.0003 (15) |
C15 | 0.0220 (16) | 0.024 (2) | 0.0259 (16) | 0.0019 (15) | 0.0003 (13) | 0.0009 (15) |
C16 | 0.0208 (16) | 0.027 (2) | 0.0204 (15) | −0.0055 (16) | −0.0016 (12) | 0.0002 (16) |
C17 | 0.0248 (18) | 0.026 (2) | 0.0219 (17) | 0.0002 (15) | 0.0007 (13) | 0.0039 (15) |
C18 | 0.0275 (18) | 0.032 (3) | 0.0275 (17) | −0.0023 (17) | 0.0031 (14) | 0.0057 (17) |
C19 | 0.0215 (18) | 0.040 (3) | 0.0330 (19) | 0.0070 (17) | 0.0078 (15) | 0.0139 (18) |
C20 | 0.0352 (19) | 0.036 (3) | 0.0208 (17) | 0.0121 (19) | 0.0049 (14) | 0.0026 (17) |
C21 | 0.0330 (19) | 0.031 (3) | 0.0207 (17) | 0.0057 (17) | −0.0006 (14) | 0.0029 (16) |
C22 | 0.0258 (17) | 0.027 (2) | 0.0175 (15) | 0.0045 (16) | 0.0010 (13) | 0.0039 (15) |
C23 | 0.0284 (17) | 0.0187 (19) | 0.0176 (15) | −0.0025 (15) | −0.0008 (13) | 0.0007 (14) |
C24 | 0.0236 (16) | 0.023 (2) | 0.0174 (16) | −0.0007 (15) | −0.0002 (13) | 0.0013 (14) |
C25 | 0.0212 (17) | 0.027 (2) | 0.0202 (16) | −0.0002 (15) | −0.0008 (13) | −0.0027 (15) |
C26 | 0.0281 (18) | 0.023 (2) | 0.0173 (16) | 0.0058 (15) | 0.0030 (13) | 0.0015 (14) |
C27 | 0.0289 (18) | 0.032 (3) | 0.0174 (16) | −0.0002 (16) | −0.0041 (13) | −0.0007 (15) |
C28 | 0.0280 (18) | 0.027 (3) | 0.0224 (17) | −0.0025 (16) | −0.0038 (14) | −0.0011 (15) |
C29 | 0.0228 (17) | 0.024 (2) | 0.0205 (16) | −0.0022 (15) | 0.0021 (13) | 0.0003 (15) |
C30 | 0.0289 (18) | 0.0209 (19) | 0.0256 (17) | 0.0020 (16) | 0.0044 (14) | 0.0014 (15) |
C31 | 0.089 (4) | 0.073 (5) | 0.059 (4) | −0.044 (4) | 0.033 (3) | −0.013 (3) |
C32 | 0.042 (3) | 0.027 (3) | 0.046 (3) | −0.0081 (19) | 0.0125 (17) | −0.012 (2) |
C33 | 0.037 (3) | 0.038 (3) | 0.054 (3) | 0.009 (2) | 0.0086 (19) | −0.005 (3) |
C34 | 0.033 (2) | 0.043 (3) | 0.033 (2) | 0.0036 (19) | −0.0010 (16) | −0.0054 (19) |
C35 | 0.0309 (19) | 0.026 (2) | 0.0289 (18) | −0.0040 (16) | 0.0039 (14) | −0.0048 (15) |
C36 | 0.036 (2) | 0.044 (3) | 0.0271 (18) | 0.0005 (19) | 0.0009 (15) | −0.0089 (18) |
Geometric parameters (Å, º) top
Cl1—C31 | 1.733 (6) | C26—C27 | 1.393 (5) |
Cl2—C31 | 1.730 (6) | C26—C30 | 1.491 (5) |
O1—C1 | 1.278 (5) | C27—C28 | 1.381 (6) |
O2—C1 | 1.256 (5) | C28—C29 | 1.395 (5) |
O3—C30 | 1.228 (4) | C32—C33 | 1.524 (6) |
O4—C30 | 1.311 (5) | C32—C35 | 1.509 (6) |
O5—C36 | 1.418 (6) | C33—C34 | 1.525 (7) |
N1—C34 | 1.504 (5) | C35—C36 | 1.505 (6) |
N1—C35 | 1.499 (5) | O4—H4O | 0.83 (5) |
C1—C2 | 1.502 (5) | O5—H5O | 0.84 (6) |
C2—C3 | 1.401 (5) | N1—H1NA | 0.99 (5) |
C2—C15 | 1.396 (5) | N1—H1NB | 1.03 (5) |
C3—C4 | 1.397 (5) | C3—H3 | 0.950 |
C4—C5 | 1.522 (5) | C5—H5 | 1.000 |
C4—C13 | 1.406 (5) | C7—H7 | 0.950 |
C5—C6 | 1.515 (5) | C8—H8 | 0.950 |
C5—C16 | 1.611 (5) | C9—H9 | 0.950 |
C6—C7 | 1.392 (6) | C10—H10 | 0.950 |
C6—C11 | 1.399 (5) | C12—H12 | 1.000 |
C7—C8 | 1.399 (5) | C14—H14 | 0.950 |
C8—C9 | 1.379 (6) | C15—H15 | 0.950 |
C9—C10 | 1.393 (6) | C16—H16 | 1.000 |
C10—C11 | 1.396 (5) | C18—H18 | 0.950 |
C11—C12 | 1.518 (5) | C19—H19 | 0.950 |
C12—C13 | 1.513 (5) | C20—H20 | 0.950 |
C12—C23 | 1.598 (5) | C21—H21 | 0.950 |
C13—C14 | 1.392 (5) | C23—H23 | 1.000 |
C14—C15 | 1.390 (5) | C25—H25 | 0.950 |
C16—C17 | 1.520 (5) | C27—H27 | 0.950 |
C16—C29 | 1.509 (5) | C28—H28 | 0.950 |
C17—C18 | 1.390 (5) | C31—H31A | 0.990 |
C17—C22 | 1.396 (5) | C31—H31B | 0.990 |
C18—C19 | 1.391 (6) | C32—H32A | 0.990 |
C19—C20 | 1.387 (6) | C32—H32B | 0.990 |
C20—C21 | 1.390 (6) | C33—H33A | 0.990 |
C21—C22 | 1.397 (5) | C33—H33B | 0.990 |
C22—C23 | 1.525 (5) | C34—H34A | 0.990 |
C23—C24 | 1.523 (5) | C34—H34B | 0.990 |
C24—C25 | 1.382 (5) | C35—H35 | 1.000 |
C24—C29 | 1.397 (5) | C36—H36A | 0.990 |
C25—C26 | 1.406 (5) | C36—H36B | 0.990 |
| | | |
O1···C3 | 2.842 (5) | C6···H14ix | 3.3055 |
O2···C15 | 2.797 (5) | C7···H14ix | 3.2539 |
O3···C27 | 2.901 (5) | C7···H15ix | 3.2181 |
O4···C25 | 2.768 (5) | C8···H15ix | 2.9667 |
O4···C27 | 3.585 (5) | C8···H31Bviii | 3.0853 |
O5···N1 | 2.826 (4) | C9···H31Bviii | 3.1281 |
C2···C13 | 2.808 (5) | C9···H33Avi | 3.0857 |
C3···C14 | 2.785 (5) | C9···H35vi | 3.2719 |
C3···C16 | 3.597 (5) | C9···H36Bviii | 3.1407 |
C3···C29 | 3.554 (5) | C10···H35vi | 3.2761 |
C4···C11 | 2.809 (5) | C10···H4Oix | 3.43 (5) |
C4···C15 | 2.789 (5) | C13···H25ix | 3.4807 |
C4···C23 | 3.229 (5) | C14···H23ix | 3.2794 |
C4···C24 | 3.044 (6) | C14···H25ix | 3.1481 |
C4···C28 | 3.525 (5) | C15···H23ix | 2.7776 |
C4···C29 | 2.752 (5) | C15···H36Biv | 3.5678 |
C5···C12 | 2.794 (5) | C17···H7xiv | 3.3463 |
C5···C18 | 3.566 (5) | C18···H5xiv | 3.2767 |
C5···C22 | 3.282 (5) | C18···H7xiv | 3.0331 |
C5···C23 | 3.216 (5) | C19···H5xiv | 2.7606 |
C5···C24 | 3.237 (6) | C19···H7xiv | 3.5793 |
C5···C28 | 3.536 (5) | C20···H5xiv | 3.0879 |
C6···C9 | 2.774 (5) | C20···H16xiv | 3.0246 |
C6···C13 | 2.830 (5) | C20···H34Bvi | 2.8726 |
C6···C17 | 2.741 (5) | C21···H16xiv | 3.1468 |
C6···C18 | 3.490 (5) | C21···H34Bvi | 3.0177 |
C6···C22 | 3.109 (6) | C22···H18xiv | 3.5029 |
C6···C23 | 3.264 (6) | C24···H18xiv | 3.2851 |
C7···C10 | 2.796 (6) | C25···H18xiv | 3.2759 |
C7···C16 | 3.519 (5) | C25···H19xiv | 3.2929 |
C7···C17 | 3.497 (6) | C26···H1NAiv | 3.50 (5) |
C8···C11 | 2.786 (6) | C26···H19xiv | 3.0851 |
C10···C22 | 3.516 (5) | C26···H32Biv | 3.5133 |
C10···C23 | 3.562 (5) | C27···H1NAiv | 3.32 (5) |
C11···C16 | 3.239 (5) | C27···H32Biv | 2.7882 |
C11···C17 | 3.061 (5) | C27···H33Biv | 3.4533 |
C11···C21 | 3.551 (6) | C27···H34Aiv | 3.5014 |
C11···C22 | 2.760 (5) | C28···H32Biv | 3.1328 |
C12···C16 | 3.217 (5) | C30···H1NAiv | 2.94 (5) |
C12···C17 | 3.249 (5) | C30···H10vi | 3.3751 |
C12···C21 | 3.554 (6) | C30···H19xiv | 3.1181 |
C12···C25 | 3.535 (5) | C30···H31Av | 3.4888 |
C12···C29 | 3.275 (5) | C30···H36Biv | 3.4508 |
C13···C16 | 3.283 (5) | C31···H5O | 3.06 (6) |
C13···C24 | 2.732 (5) | C31···H8vii | 3.0960 |
C13···C25 | 3.451 (6) | C31···H9vii | 3.3682 |
C13···C29 | 3.114 (5) | C31···H32Aiv | 3.3729 |
C14···C23 | 3.539 (5) | C31···H33Aiv | 3.1646 |
C14···C24 | 3.517 (5) | C31···H36A | 3.3737 |
C16···C23 | 2.782 (5) | C32···H5Oiii | 3.31 (7) |
C17···C20 | 2.779 (5) | C32···H9ix | 3.5104 |
C17···C24 | 2.831 (5) | C32···H27iii | 3.2504 |
C18···C21 | 2.796 (6) | C32···H31Biii | 3.5708 |
C19···C22 | 2.777 (5) | C33···H9ix | 3.3732 |
C22···C29 | 2.805 (5) | C33···H27iii | 3.1872 |
C24···C27 | 2.784 (5) | C33···H31Biii | 3.1229 |
C25···C28 | 2.786 (5) | C34···H20ix | 3.3536 |
C26···C29 | 2.784 (5) | C34···H27iii | 3.0994 |
Cl1···O3i | 3.444 (3) | C35···H9ix | 3.4768 |
Cl1···C34ii | 3.547 (4) | C35···H10ix | 3.5884 |
Cl2···C34iii | 3.473 (5) | C36···H9vii | 2.9342 |
O1···O3i | 3.360 (4) | C36···H31A | 2.9538 |
O1···O4i | 2.534 (4) | H1NA···Cl2iv | 3.52 (5) |
O1···O5 | 2.695 (4) | H1NA···O2 | 3.19 (5) |
O1···N1 | 3.495 (4) | H1NA···O3iii | 1.90 (5) |
O1···C30i | 3.331 (5) | H1NA···C26iii | 3.50 (5) |
O1···C35 | 3.451 (5) | H1NA···C27iii | 3.32 (5) |
O1···C36 | 3.537 (5) | H1NA···C30iii | 2.94 (5) |
O2···O5 | 3.487 (4) | H1NA···H27iii | 2.7322 |
O2···N1 | 2.708 (4) | H1NA···H31Aiv | 3.3570 |
O2···C34 | 3.453 (5) | H1NA···H36Aiv | 3.5340 |
O2···C36iv | 3.475 (5) | H1NB···O1 | 2.72 (5) |
O3···Cl1v | 3.444 (3) | H1NB···O2 | 1.68 (5) |
O3···O1v | 3.360 (4) | H1NB···O3iii | 3.35 (5) |
O3···N1iv | 2.886 (4) | H1NB···C1 | 2.50 (5) |
O3···C31v | 3.254 (7) | H1NB···H10ix | 3.3600 |
O4···O1v | 2.534 (4) | H1NB···H21ix | 3.4882 |
O4···C1v | 3.444 (5) | H1NB···H36Aiv | 3.1199 |
O4···C3v | 3.288 (5) | H3···O4i | 2.5668 |
O4···C10vi | 3.529 (5) | H3···H12ix | 3.3969 |
O5···O1 | 2.695 (4) | H3···H19xi | 3.1337 |
O5···O2 | 3.487 (4) | H3···H32Aiv | 3.5922 |
O5···C1 | 3.375 (4) | H3···H32Biv | 3.4980 |
O5···C9vii | 3.267 (5) | H3···H4Oi | 2.3162 |
O5···C31 | 3.127 (7) | H5···C18xi | 3.2767 |
O5···C32iv | 3.283 (6) | H5···C19xi | 2.7606 |
O5···C35iv | 3.571 (6) | H5···C20xi | 3.0879 |
N1···O1 | 3.495 (4) | H5···H14ix | 3.5017 |
N1···O2 | 2.708 (4) | H5···H18xi | 3.5978 |
N1···O3iii | 2.886 (4) | H5···H19xi | 2.7784 |
N1···C1 | 3.485 (5) | H5···H20xi | 3.2907 |
C1···O4i | 3.444 (5) | H5O···O1 | 1.90 (6) |
C1···O5 | 3.375 (4) | H5O···O2 | 3.06 (6) |
C1···N1 | 3.485 (5) | H5O···O3i | 3.41 (7) |
C3···O4i | 3.288 (5) | H5O···C1 | 2.75 (6) |
C9···O5viii | 3.267 (5) | H5O···C31 | 3.06 (6) |
C9···C36viii | 3.592 (6) | H5O···C32iv | 3.31 (7) |
C10···O4ix | 3.529 (5) | H5O···H9vii | 3.1190 |
C30···O1v | 3.331 (5) | H5O···H31A | 2.2278 |
C31···O3i | 3.254 (7) | H5O···H31B | 3.1498 |
C31···O5 | 3.127 (7) | H5O···H32Aiv | 2.3505 |
C32···O5iii | 3.283 (6) | H5O···H35iv | 3.5182 |
C34···Cl1x | 3.547 (4) | H5O···H4Oi | 3.00 (8) |
C34···Cl2iv | 3.473 (5) | H7···C17xi | 3.3463 |
C34···O2 | 3.453 (5) | H7···C18xi | 3.0331 |
C35···O1 | 3.451 (5) | H7···C19xi | 3.5793 |
C35···O5iii | 3.571 (6) | H7···H14ix | 3.3861 |
C36···O1 | 3.537 (5) | H7···H15ix | 3.2799 |
C36···O2iii | 3.475 (5) | H7···H16xi | 3.3407 |
C36···C9vii | 3.592 (6) | H7···H18xi | 2.9868 |
O1···H3 | 2.5477 | H8···Cl2viii | 2.9999 |
O2···H15 | 2.4892 | H8···C31viii | 3.0960 |
O3···H27 | 2.6577 | H8···H15ix | 2.8546 |
O3···H4O | 2.27 (5) | H8···H28xi | 3.4533 |
O4···H25 | 2.4883 | H8···H31Aviii | 3.3229 |
O5···H1NA | 2.85 (5) | H8···H31Bviii | 2.5238 |
O5···H1NB | 2.74 (5) | H8···H36Aviii | 3.5754 |
O5···H35 | 2.6941 | H9···O5viii | 2.3764 |
N1···H5O | 2.86 (6) | H9···C31viii | 3.3682 |
N1···H32A | 3.2175 | H9···C32vi | 3.5104 |
N1···H32B | 2.7052 | H9···C33vi | 3.3732 |
N1···H33A | 3.0323 | H9···C35vi | 3.4768 |
N1···H33B | 3.1377 | H9···C36viii | 2.9342 |
N1···H36A | 3.3142 | H9···H5Oviii | 3.1190 |
N1···H36B | 2.7232 | H9···H31Aviii | 3.2388 |
C1···H3 | 2.6925 | H9···H31Bviii | 2.6142 |
C1···H15 | 2.6538 | H9···H32Avi | 3.1611 |
C2···H14 | 3.2766 | H9···H33Avi | 2.6145 |
C3···H5 | 2.6132 | H9···H35vi | 2.6738 |
C3···H15 | 3.2669 | H9···H36Aviii | 3.1860 |
C4···H12 | 3.2837 | H9···H36Bviii | 2.6721 |
C4···H14 | 3.2762 | H10···O1vi | 2.7044 |
C4···H16 | 3.2516 | H10···O2vi | 3.3431 |
C5···H3 | 2.7198 | H10···O3ix | 3.5853 |
C5···H7 | 2.7190 | H10···O4ix | 2.9092 |
C6···H8 | 3.2667 | H10···C1vi | 3.0464 |
C6···H10 | 3.2765 | H10···C30ix | 3.3751 |
C6···H12 | 3.2917 | H10···C35vi | 3.5884 |
C6···H16 | 3.2000 | H10···H1NBvi | 3.3600 |
C7···H5 | 2.6082 | H10···H34Bvi | 3.4914 |
C7···H9 | 3.2642 | H10···H35vi | 2.6845 |
C8···H10 | 3.2654 | H10···H4Oix | 2.6488 |
C9···H7 | 3.2659 | H12···O1vi | 3.4175 |
C10···H8 | 3.2652 | H12···O4ix | 3.1047 |
C10···H12 | 2.6198 | H12···C1vi | 3.2053 |
C11···H5 | 3.2905 | H12···C2vi | 3.0513 |
C11···H7 | 3.2813 | H12···C3vi | 3.2415 |
C11···H9 | 3.2655 | H12···H3vi | 3.3969 |
C11···H23 | 3.2411 | H12···H25ix | 3.4493 |
C12···H10 | 2.7365 | H12···H4Oix | 3.1065 |
C12···H14 | 2.7435 | H14···C4vi | 3.5563 |
C13···H3 | 3.2801 | H14···C6vi | 3.3055 |
C13···H5 | 3.3086 | H14···C7vi | 3.2539 |
C13···H15 | 3.2673 | H14···H5vi | 3.5017 |
C13···H23 | 3.1882 | H14···H7vi | 3.3861 |
C14···H12 | 2.6293 | H14···H23ix | 3.5750 |
C15···H3 | 3.2665 | H14···H25ix | 3.0731 |
C16···H18 | 2.7373 | H15···C7vi | 3.2181 |
C16···H28 | 2.7267 | H15···C8vi | 2.9667 |
C17···H5 | 3.2536 | H15···H7vi | 3.2799 |
C17···H19 | 3.2608 | H15···H8vi | 2.8546 |
C17···H21 | 3.2796 | H15···H21ix | 3.0430 |
C17···H23 | 3.2944 | H15···H23ix | 2.7828 |
C18···H16 | 2.6214 | H15···H36Aiv | 3.4003 |
C18···H20 | 3.2661 | H15···H36Biv | 3.4225 |
C19···H21 | 3.2681 | H16···C20xi | 3.0246 |
C20···H18 | 3.2684 | H16···C21xi | 3.1468 |
C21···H19 | 3.2652 | H16···H7xiv | 3.3407 |
C21···H23 | 2.6171 | H16···H20xi | 3.0645 |
C22···H12 | 3.2143 | H16···H21xi | 3.2779 |
C22···H16 | 3.2797 | H18···C22xi | 3.5029 |
C22···H18 | 3.2736 | H18···C24xi | 3.2851 |
C22···H20 | 3.2639 | H18···C25xi | 3.2759 |
C23···H21 | 2.7360 | H18···H5xiv | 3.5978 |
C23···H25 | 2.7182 | H18···H7xiv | 2.9868 |
C24···H12 | 3.2429 | H18···H23xi | 3.4684 |
C24···H16 | 3.2818 | H18···H25xi | 3.4120 |
C24···H28 | 3.2701 | H19···Cl1xiv | 3.4339 |
C25···H23 | 2.6119 | H19···O4xi | 2.8048 |
C25···H27 | 3.2825 | H19···C25xi | 3.2929 |
C25···H4O | 3.58 (5) | H19···C26xi | 3.0851 |
C26···H28 | 3.2597 | H19···C30xi | 3.1181 |
C26···H4O | 3.06 (5) | H19···H3xiv | 3.1337 |
C27···H25 | 3.2819 | H19···H5xiv | 2.7784 |
C28···H16 | 2.6104 | H19···H25xi | 3.3434 |
C29···H5 | 3.2069 | H19···H4Oxi | 3.2976 |
C29···H23 | 3.2858 | H20···Cl1xiv | 2.8749 |
C29···H25 | 3.2703 | H20···Cl2xv | 3.4142 |
C29···H27 | 3.2662 | H20···C34vi | 3.3536 |
C30···H25 | 2.6785 | H20···H5xiv | 3.2907 |
C30···H27 | 2.6504 | H20···H16xiv | 3.0645 |
C32···H1NA | 2.70 (5) | H20···H28xiv | 3.2666 |
C32···H1NB | 3.23 (5) | H20···H34Avi | 3.2127 |
C32···H34A | 3.0309 | H20···H34Bvi | 2.6154 |
C32···H34B | 3.1381 | H21···O2vi | 2.8052 |
C32···H36A | 2.8407 | H21···C1vi | 3.5748 |
C32···H36B | 2.6900 | H21···H1NBvi | 3.4882 |
C33···H1NA | 2.94 (5) | H21···H15vi | 3.0430 |
C33···H1NB | 3.21 (5) | H21···H16xiv | 3.2779 |
C33···H35 | 2.6848 | H21···H34Bvi | 2.8729 |
C34···H32A | 3.2461 | H23···C1vi | 3.5524 |
C34···H32B | 2.8608 | H23···C2vi | 3.1339 |
C34···H35 | 2.7470 | H23···C14vi | 3.2794 |
C35···H5O | 2.43 (6) | H23···C15vi | 2.7776 |
C35···H33A | 2.8235 | H23···H14vi | 3.5750 |
C35···H33B | 3.2115 | H23···H15vi | 2.7828 |
C35···H34A | 3.1644 | H23···H18xiv | 3.4684 |
C35···H34B | 2.9433 | H25···C13vi | 3.4807 |
C36···H1NA | 2.51 (5) | H25···C14vi | 3.1481 |
C36···H1NB | 2.86 (5) | H25···H12vi | 3.4493 |
C36···H32A | 2.9394 | H25···H14vi | 3.0731 |
C36···H32B | 2.6824 | H25···H18xiv | 3.4120 |
H1NA···H5O | 3.14 (8) | H25···H19xiv | 3.3434 |
H1NA···H32B | 2.6919 | H27···N1iv | 3.3075 |
H1NA···H33B | 3.4301 | H27···C32iv | 3.2504 |
H1NA···H34A | 2.2146 | H27···C33iv | 3.1872 |
H1NA···H34B | 2.8008 | H27···C34iv | 3.0994 |
H1NA···H35 | 2.8319 | H27···H1NAiv | 2.7322 |
H1NA···H36A | 3.4638 | H27···H32Biv | 2.6064 |
H1NA···H36B | 2.4201 | H27···H33Biv | 2.8194 |
H1NB···H5O | 2.55 (7) | H27···H34Aiv | 2.5708 |
H1NB···H34A | 2.6556 | H28···Cl2xvi | 2.9670 |
H1NB···H34B | 2.2095 | H28···H8xiv | 3.4533 |
H1NB···H35 | 2.2727 | H28···H20xi | 3.2666 |
H1NB···H36B | 3.3047 | H28···H32Biv | 3.2035 |
H3···H5 | 2.4255 | H28···H33Biv | 3.1650 |
H5···H7 | 2.4315 | H31A···O1 | 3.3253 |
H5···H16 | 2.2436 | H31A···O3i | 2.6412 |
H5O···H35 | 2.3823 | H31A···O5 | 2.3870 |
H5O···H36A | 2.2366 | H31A···C30i | 3.4888 |
H5O···H36B | 2.6231 | H31A···C36 | 2.9538 |
H7···H8 | 2.3525 | H31A···H1NAiii | 3.3570 |
H8···H9 | 2.3214 | H31A···H5O | 2.2278 |
H9···H10 | 2.3410 | H31A···H8vii | 3.3229 |
H10···H12 | 2.4497 | H31A···H9vii | 3.2388 |
H12···H14 | 2.4625 | H31A···H32Aiv | 3.1636 |
H12···H23 | 2.2275 | H31A···H33Aiv | 3.5332 |
H14···H15 | 2.3321 | H31A···H36A | 2.5417 |
H16···H18 | 2.4550 | H31A···H4Oi | 3.3463 |
H16···H28 | 2.4293 | H31B···O5 | 2.9961 |
H18···H19 | 2.3414 | H31B···C8vii | 3.0853 |
H19···H20 | 2.3312 | H31B···C9vii | 3.1281 |
H20···H21 | 2.3415 | H31B···C32iv | 3.5708 |
H21···H23 | 2.4397 | H31B···C33iv | 3.1229 |
H23···H25 | 2.4338 | H31B···H5O | 3.1498 |
H25···H4O | 3.2658 | H31B···H8vii | 2.5238 |
H27···H28 | 2.3280 | H31B···H9vii | 2.6142 |
H32A···H33A | 2.2778 | H31B···H32Aiv | 3.0366 |
H32A···H33B | 2.5925 | H31B···H33Aiv | 2.3268 |
H32A···H35 | 2.2982 | H31B···H33Biv | 3.3178 |
H32A···H36A | 2.8855 | H31B···H36A | 3.5271 |
H32A···H36B | 3.1802 | H32A···Cl1iii | 3.4065 |
H32B···H33A | 2.8591 | H32A···O1iii | 2.7513 |
H32B···H33B | 2.2802 | H32A···O2iii | 3.5831 |
H32B···H34A | 3.1963 | H32A···O5iii | 2.4294 |
H32B···H35 | 2.8695 | H32A···C1iii | 3.0394 |
H32B···H36A | 3.0149 | H32A···C31iii | 3.3729 |
H32B···H36B | 2.4400 | H32A···H3iii | 3.5922 |
H33A···H34A | 2.7790 | H32A···H5Oiii | 2.3505 |
H33A···H34B | 2.2253 | H32A···H9ix | 3.1611 |
H33A···H35 | 2.7742 | H32A···H31Aiii | 3.1636 |
H33B···H34A | 2.2250 | H32A···H31Biii | 3.0366 |
H33B···H34B | 2.7035 | H32B···C1iii | 3.5247 |
H34B···H35 | 2.9790 | H32B···C2iii | 3.4303 |
H35···H36A | 2.3183 | H32B···C3iii | 3.5015 |
H35···H36B | 2.8578 | H32B···C26iii | 3.5133 |
Cl1···H19xi | 3.4339 | H32B···C27iii | 2.7882 |
Cl1···H20xi | 2.8749 | H32B···C28iii | 3.1328 |
Cl1···H32Aiv | 3.4065 | H32B···H3iii | 3.4980 |
Cl1···H33Aiv | 3.4679 | H32B···H27iii | 2.6064 |
Cl1···H33Bii | 3.3557 | H32B···H28iii | 3.2035 |
Cl1···H33Biv | 3.4067 | H33A···Cl1iii | 3.4679 |
Cl1···H34Aii | 2.9414 | H33A···O5iii | 3.5918 |
Cl1···H34Bii | 3.5147 | H33A···C9ix | 3.0857 |
Cl1···H4Oi | 3.50 (5) | H33A···C31iii | 3.1646 |
Cl2···H1NAiii | 3.52 (5) | H33A···H9ix | 2.6145 |
Cl2···H8vii | 2.9999 | H33A···H31Aiii | 3.5332 |
Cl2···H20xii | 3.4142 | H33A···H31Biii | 2.3268 |
Cl2···H28xiii | 2.9670 | H33B···Cl1x | 3.3557 |
Cl2···H33Bii | 2.9194 | H33B···Cl1iii | 3.4067 |
Cl2···H34Aiii | 2.8540 | H33B···Cl2x | 2.9194 |
Cl2···H34Biii | 3.4928 | H33B···C27iii | 3.4533 |
O1···H1NB | 2.72 (5) | H33B···H27iii | 2.8194 |
O1···H5O | 1.90 (6) | H33B···H28iii | 3.1650 |
O1···H10ix | 2.7044 | H33B···H31Biii | 3.3178 |
O1···H12ix | 3.4175 | H34A···Cl1x | 2.9414 |
O1···H31A | 3.3253 | H34A···Cl2iv | 2.8540 |
O1···H32Aiv | 2.7513 | H34A···O3iii | 3.3944 |
O1···H35 | 2.9519 | H34A···C27iii | 3.5014 |
O1···H4Oi | 1.72 (5) | H34A···H20ix | 3.2127 |
O2···H1NA | 3.19 (5) | H34A···H27iii | 2.5708 |
O2···H1NB | 1.68 (5) | H34B···Cl1x | 3.5147 |
O2···H5O | 3.06 (6) | H34B···Cl2iv | 3.4928 |
O2···H10ix | 3.3431 | H34B···O2 | 3.1555 |
O2···H21ix | 2.8052 | H34B···C20ix | 2.8726 |
O2···H32Aiv | 3.5831 | H34B···C21ix | 3.0177 |
O2···H34B | 3.1555 | H34B···H10ix | 3.4914 |
O2···H35 | 3.4687 | H34B···H20ix | 2.6154 |
O2···H36Aiv | 2.5715 | H34B···H21ix | 2.8729 |
O3···H1NAiv | 1.90 (5) | H35···O1 | 2.9519 |
O3···H1NBiv | 3.35 (5) | H35···O2 | 3.4687 |
O3···H5Ov | 3.41 (7) | H35···O3i | 3.5482 |
O3···H10vi | 3.5853 | H35···O5iii | 3.0615 |
O3···H31Av | 2.6412 | H35···C1 | 3.5911 |
O3···H34Aiv | 3.3944 | H35···C9ix | 3.2719 |
O3···H35v | 3.5482 | H35···C10ix | 3.2761 |
O3···H36Biv | 3.0418 | H35···H5Oiii | 3.5182 |
O4···H3v | 2.5668 | H35···H9ix | 2.6738 |
O4···H10vi | 2.9092 | H35···H10ix | 2.6845 |
O4···H12vi | 3.1047 | H36A···O2iii | 2.5715 |
O4···H19xiv | 2.8048 | H36A···C1iii | 3.0591 |
O5···H9vii | 2.3764 | H36A···C31 | 3.3737 |
O5···H31A | 2.3870 | H36A···H1NAiii | 3.5340 |
O5···H31B | 2.9961 | H36A···H1NBiii | 3.1199 |
O5···H32Aiv | 2.4294 | H36A···H8vii | 3.5754 |
O5···H33Aiv | 3.5918 | H36A···H9vii | 3.1860 |
O5···H35iv | 3.0615 | H36A···H15iii | 3.4003 |
N1···H27iii | 3.3075 | H36A···H31A | 2.5417 |
C1···H1NB | 2.50 (5) | H36A···H31B | 3.5271 |
C1···H5O | 2.75 (6) | H36B···O3iii | 3.0418 |
C1···H10ix | 3.0464 | H36B···C9vii | 3.1407 |
C1···H12ix | 3.2053 | H36B···C15iii | 3.5678 |
C1···H21ix | 3.5748 | H36B···C30iii | 3.4508 |
C1···H23ix | 3.5524 | H36B···H9vii | 2.6721 |
C1···H32Aiv | 3.0394 | H36B···H15iii | 3.4225 |
C1···H32Biv | 3.5247 | H4O···Cl1v | 3.50 (5) |
C1···H35 | 3.5911 | H4O···O1v | 1.72 (5) |
C1···H36Aiv | 3.0591 | H4O···C1v | 2.72 (5) |
C1···H4Oi | 2.72 (5) | H4O···C2v | 3.23 (5) |
C2···H12ix | 3.0513 | H4O···C3v | 2.99 (5) |
C2···H23ix | 3.1339 | H4O···C10vi | 3.43 (5) |
C2···H32Biv | 3.4303 | H4O···H3v | 2.3162 |
C2···H4Oi | 3.23 (5) | H4O···H5Ov | 3.00 (8) |
C3···H12ix | 3.2415 | H4O···H10vi | 2.6488 |
C3···H32Biv | 3.5015 | H4O···H12vi | 3.1065 |
C3···H4Oi | 2.99 (5) | H4O···H19xiv | 3.2976 |
C4···H14ix | 3.5563 | H4O···H31Av | 3.3463 |
| | | |
C34—N1—C35 | 106.0 (3) | C34—N1—H1NA | 110 (3) |
O1—C1—O2 | 123.0 (4) | C34—N1—H1NB | 109 (3) |
O1—C1—C2 | 118.4 (3) | C35—N1—H1NA | 108 (3) |
O2—C1—C2 | 118.5 (3) | C35—N1—H1NB | 110 (3) |
C1—C2—C3 | 121.4 (3) | H1NA—N1—H1NB | 112 (4) |
C1—C2—C15 | 119.7 (3) | C2—C3—H3 | 119.648 |
C3—C2—C15 | 118.9 (3) | C4—C3—H3 | 119.658 |
C2—C3—C4 | 120.7 (4) | C4—C5—H5 | 108.730 |
C3—C4—C5 | 122.2 (3) | C6—C5—H5 | 108.732 |
C3—C4—C13 | 119.7 (3) | C16—C5—H5 | 108.739 |
C5—C4—C13 | 118.0 (3) | C6—C7—H7 | 120.356 |
C4—C5—C6 | 107.1 (3) | C8—C7—H7 | 120.348 |
C4—C5—C16 | 112.7 (3) | C7—C8—H8 | 119.891 |
C6—C5—C16 | 110.7 (3) | C9—C8—H8 | 119.879 |
C5—C6—C7 | 122.2 (3) | C8—C9—H9 | 119.603 |
C5—C6—C11 | 117.3 (3) | C10—C9—H9 | 119.608 |
C7—C6—C11 | 120.5 (3) | C9—C10—H10 | 120.248 |
C6—C7—C8 | 119.3 (4) | C11—C10—H10 | 120.254 |
C7—C8—C9 | 120.2 (4) | C11—C12—H12 | 108.348 |
C8—C9—C10 | 120.8 (4) | C13—C12—H12 | 108.351 |
C9—C10—C11 | 119.5 (4) | C23—C12—H12 | 108.344 |
C6—C11—C10 | 119.7 (4) | C13—C14—H14 | 119.829 |
C6—C11—C12 | 117.5 (3) | C15—C14—H14 | 119.829 |
C10—C11—C12 | 122.9 (3) | C2—C15—H15 | 119.616 |
C11—C12—C13 | 107.8 (3) | C14—C15—H15 | 119.603 |
C11—C12—C23 | 112.9 (3) | C5—C16—H16 | 108.166 |
C13—C12—C23 | 111.1 (3) | C17—C16—H16 | 108.165 |
C4—C13—C12 | 116.4 (3) | C29—C16—H16 | 108.175 |
C4—C13—C14 | 119.6 (3) | C17—C18—H18 | 120.229 |
C12—C13—C14 | 124.0 (3) | C19—C18—H18 | 120.226 |
C13—C14—C15 | 120.3 (4) | C18—C19—H19 | 119.789 |
C2—C15—C14 | 120.8 (4) | C20—C19—H19 | 119.798 |
C5—C16—C17 | 113.0 (3) | C19—C20—H20 | 119.791 |
C5—C16—C29 | 111.5 (3) | C21—C20—H20 | 119.780 |
C17—C16—C29 | 107.7 (3) | C20—C21—H21 | 120.330 |
C16—C17—C18 | 123.1 (4) | C22—C21—H21 | 120.334 |
C16—C17—C22 | 116.8 (3) | C12—C23—H23 | 108.323 |
C18—C17—C22 | 120.1 (4) | C22—C23—H23 | 108.315 |
C17—C18—C19 | 119.5 (4) | C24—C23—H23 | 108.316 |
C18—C19—C20 | 120.4 (4) | C24—C25—H25 | 120.211 |
C19—C20—C21 | 120.4 (4) | C26—C25—H25 | 120.222 |
C20—C21—C22 | 119.3 (4) | C26—C27—H27 | 120.007 |
C17—C22—C21 | 120.1 (4) | C28—C27—H27 | 120.005 |
C17—C22—C23 | 117.4 (3) | C27—C28—H28 | 119.791 |
C21—C22—C23 | 122.5 (3) | C29—C28—H28 | 119.789 |
C12—C23—C22 | 112.0 (3) | Cl1—C31—H31A | 108.352 |
C12—C23—C24 | 112.7 (3) | Cl1—C31—H31B | 108.353 |
C22—C23—C24 | 107.0 (3) | Cl2—C31—H31A | 108.356 |
C23—C24—C25 | 122.5 (3) | Cl2—C31—H31B | 108.356 |
C23—C24—C29 | 117.0 (3) | H31A—C31—H31B | 107.436 |
C25—C24—C29 | 120.4 (3) | C33—C32—H32A | 111.026 |
C24—C25—C26 | 119.6 (4) | C33—C32—H32B | 111.030 |
C25—C26—C27 | 119.9 (4) | C35—C32—H32A | 111.033 |
C25—C26—C30 | 120.3 (3) | C35—C32—H32B | 111.030 |
C27—C26—C30 | 119.7 (3) | H32A—C32—H32B | 109.020 |
C26—C27—C28 | 120.0 (3) | C32—C33—H33A | 110.712 |
C27—C28—C29 | 120.4 (4) | C32—C33—H33B | 110.717 |
C16—C29—C24 | 117.3 (3) | C34—C33—H33A | 110.715 |
C16—C29—C28 | 123.1 (3) | C34—C33—H33B | 110.718 |
C24—C29—C28 | 119.6 (4) | H33A—C33—H33B | 108.814 |
O3—C30—O4 | 123.6 (4) | N1—C34—H34A | 110.479 |
O3—C30—C26 | 123.2 (4) | N1—C34—H34B | 110.481 |
O4—C30—C26 | 113.2 (3) | C33—C34—H34A | 110.484 |
Cl1—C31—Cl2 | 115.7 (4) | C33—C34—H34B | 110.481 |
C33—C32—C35 | 103.6 (4) | H34A—C34—H34B | 108.668 |
C32—C33—C34 | 105.1 (4) | N1—C35—H35 | 109.079 |
N1—C34—C33 | 106.2 (3) | C32—C35—H35 | 109.070 |
N1—C35—C32 | 102.9 (3) | C36—C35—H35 | 109.073 |
N1—C35—C36 | 110.2 (4) | O5—C36—H36A | 109.187 |
C32—C35—C36 | 116.2 (4) | O5—C36—H36B | 109.185 |
O5—C36—C35 | 112.1 (3) | C35—C36—H36A | 109.183 |
C30—O4—H4O | 109 (4) | C35—C36—H36B | 109.189 |
C36—O5—H5O | 105 (5) | H36A—C36—H36B | 107.891 |
| | | |
C34—N1—C35—C32 | 35.5 (4) | C12—C13—C14—C15 | −177.6 (3) |
C34—N1—C35—C36 | 160.0 (3) | C13—C14—C15—C2 | 0.9 (5) |
C35—N1—C34—C33 | −16.9 (4) | C5—C16—C17—C18 | 101.7 (4) |
O1—C1—C2—C3 | 1.9 (5) | C5—C16—C17—C22 | −79.0 (4) |
O1—C1—C2—C15 | −177.6 (3) | C5—C16—C29—C24 | 77.4 (4) |
O2—C1—C2—C3 | −178.0 (3) | C5—C16—C29—C28 | −101.7 (4) |
O2—C1—C2—C15 | 2.5 (5) | C17—C16—C29—C24 | −47.1 (4) |
C1—C2—C3—C4 | −177.9 (3) | C17—C16—C29—C28 | 133.8 (3) |
C1—C2—C15—C14 | 177.4 (3) | C29—C16—C17—C18 | −134.7 (3) |
C3—C2—C15—C14 | −2.1 (5) | C29—C16—C17—C22 | 44.5 (4) |
C15—C2—C3—C4 | 1.6 (5) | C16—C17—C18—C19 | 178.0 (3) |
C2—C3—C4—C5 | 177.0 (3) | C16—C17—C22—C21 | −177.5 (3) |
C2—C3—C4—C13 | 0.2 (5) | C16—C17—C22—C23 | 2.5 (5) |
C3—C4—C5—C6 | −131.7 (3) | C18—C17—C22—C21 | 1.7 (5) |
C3—C4—C5—C16 | 106.2 (4) | C18—C17—C22—C23 | −178.2 (3) |
C3—C4—C13—C12 | 177.1 (3) | C22—C17—C18—C19 | −1.2 (5) |
C3—C4—C13—C14 | −1.5 (5) | C17—C18—C19—C20 | −0.4 (6) |
C5—C4—C13—C12 | 0.2 (5) | C18—C19—C20—C21 | 1.4 (6) |
C5—C4—C13—C14 | −178.4 (3) | C19—C20—C21—C22 | −0.8 (6) |
C13—C4—C5—C6 | 45.1 (4) | C20—C21—C22—C17 | −0.8 (5) |
C13—C4—C5—C16 | −76.9 (4) | C20—C21—C22—C23 | 179.2 (3) |
C4—C5—C6—C7 | 134.8 (3) | C17—C22—C23—C12 | 77.0 (4) |
C4—C5—C6—C11 | −45.0 (4) | C17—C22—C23—C24 | −47.0 (4) |
C4—C5—C16—C17 | 118.7 (3) | C21—C22—C23—C12 | −103.0 (4) |
C4—C5—C16—C29 | −2.7 (4) | C21—C22—C23—C24 | 133.0 (3) |
C6—C5—C16—C17 | −1.2 (4) | C12—C23—C24—C25 | 100.9 (4) |
C6—C5—C16—C29 | −122.7 (3) | C12—C23—C24—C29 | −79.0 (4) |
C16—C5—C6—C7 | −101.9 (4) | C22—C23—C24—C25 | −135.5 (3) |
C16—C5—C6—C11 | 78.3 (4) | C22—C23—C24—C29 | 44.6 (4) |
C5—C6—C7—C8 | −179.8 (3) | C23—C24—C25—C26 | −179.3 (3) |
C5—C6—C11—C10 | −179.7 (3) | C23—C24—C29—C16 | 2.1 (5) |
C5—C6—C11—C12 | 0.1 (5) | C23—C24—C29—C28 | −178.8 (3) |
C7—C6—C11—C10 | 0.5 (5) | C25—C24—C29—C16 | −177.9 (3) |
C7—C6—C11—C12 | −179.7 (3) | C25—C24—C29—C28 | 1.3 (5) |
C11—C6—C7—C8 | −0.0 (6) | C29—C24—C25—C26 | 0.7 (5) |
C6—C7—C8—C9 | 0.3 (6) | C24—C25—C26—C27 | −2.0 (5) |
C7—C8—C9—C10 | −1.0 (6) | C24—C25—C26—C30 | 177.9 (3) |
C8—C9—C10—C11 | 1.5 (6) | C25—C26—C27—C28 | 1.4 (5) |
C9—C10—C11—C6 | −1.2 (6) | C25—C26—C30—O3 | −154.7 (4) |
C9—C10—C11—C12 | 179.0 (3) | C25—C26—C30—O4 | 24.8 (5) |
C6—C11—C12—C13 | 45.7 (4) | C27—C26—C30—O3 | 25.2 (5) |
C6—C11—C12—C23 | −77.3 (4) | C27—C26—C30—O4 | −155.4 (3) |
C10—C11—C12—C13 | −134.4 (4) | C30—C26—C27—C28 | −178.4 (3) |
C10—C11—C12—C23 | 102.6 (4) | C26—C27—C28—C29 | 0.5 (6) |
C11—C12—C13—C4 | −45.5 (4) | C27—C28—C29—C16 | 177.2 (3) |
C11—C12—C13—C14 | 133.1 (3) | C27—C28—C29—C24 | −1.8 (6) |
C11—C12—C23—C22 | −2.0 (4) | C33—C32—C35—N1 | −40.1 (4) |
C11—C12—C23—C24 | 118.8 (3) | C33—C32—C35—C36 | −160.6 (3) |
C13—C12—C23—C22 | −123.1 (3) | C35—C32—C33—C34 | 29.7 (4) |
C13—C12—C23—C24 | −2.4 (4) | C32—C33—C34—N1 | −8.0 (4) |
C23—C12—C13—C4 | 78.6 (4) | N1—C35—C36—O5 | 52.4 (4) |
C23—C12—C13—C14 | −102.8 (4) | C32—C35—C36—O5 | 168.9 (4) |
C4—C13—C14—C15 | 1.0 (5) | | |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1; (iv) −x, y−1/2, −z+1; (v) x, y−1, z; (vi) −x, y−1/2, −z; (vii) x, y, z+1; (viii) x, y, z−1; (ix) −x, y+1/2, −z; (x) x−1, y, z; (xi) −x+1, y+1/2, −z; (xii) x, y+1, z+1; (xiii) −x+1, y+1/2, −z+1; (xiv) −x+1, y−1/2, −z; (xv) x, y−1, z−1; (xvi) −x+1, y−1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1v | 0.83 (5) | 1.72 (5) | 2.534 (4) | 167 (5) |
O5—H5O···O1 | 0.84 (6) | 1.90 (6) | 2.695 (4) | 156 (7) |
N1—H1NA···O3iii | 0.99 (5) | 1.90 (5) | 2.886 (4) | 172 (5) |
N1—H1NB···O2 | 1.03 (5) | 1.68 (5) | 2.708 (4) | 173 (4) |
Symmetry codes: (iii) −x, y+1/2, −z+1; (v) x, y−1, z. |
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