organic compounds
The title compound, C30H33NO6·1.5CHCl3, a derivative of L-DOPA, forms chains in its crystal structure, via weak N—HO=C hydrogen bonds involving the carbamate N—H and carbonyl groups of adjacent molecules, supported by N—HO=C interactions of the same carbonyl. The staggered conformation about the C—C bond joining the dimethoxyphenyl group to the chiral centre is similar to that in L-DOPA, but different from that in the iodo derivative from which the title compound was prepared. Extensive disorder of the chloroform solvent molecules, which could not be modelled by discrete atomic sites, prevents the confirmation of the absolute configuration of the main molecule on the basis of anomalous scattering effects of chlorine atoms, demonstrating a limitation of this otherwise useful technique.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025819/bt6382sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025819/bt6382Isup2.hkl |
CCDC reference: 227890
Computing details top
Data collection: DIF4 (Stoe & Cie, 1988); cell refinement: DIF4; data reduction: local programs; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(3',4'-dimethoxyphenyl)propionic acid tert-butyl ester chloroform
sesquisolvate top
Crystal data top
C30H33NO6·1.5CHCl3 | F(000) = 710 |
Mr = 682.63 | Dx = 1.408 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 12.1419 (11) Å | Cell parameters from 56 reflections |
b = 5.3779 (6) Å | θ = 19.2–24.9° |
c = 24.926 (2) Å | µ = 4.09 mm−1 |
β = 98.435 (10)° | T = 160 K |
V = 1610.0 (3) Å3 | Plate, colourless |
Z = 2 | 0.33 × 0.15 × 0.08 mm |
Data collection top
Stoe-Siemens four-circle diffractometer | 4567 reflections with I > 2σ(I) |
Radiation source: Bede Microsource | Rint = 0.037 |
8 micron Ni filter monochromator | θmax = 67.2°, θmin = 3.6° |
ω/θ scans with on–line profile fitting (Clegg, 1981) | h = −14→14 |
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2001) | k = −6→6 |
Tmin = 0.571, Tmax = 0.721 | l = −27→28 |
8184 measured reflections | 5 standard reflections every 60 min |
5020 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0588P)2 + 1.03P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.153 | (Δ/σ)max < 0.001 |
S = 1.14 | Δρmax = 0.31 e Å−3 |
5020 reflections | Δρmin = −0.28 e Å−3 |
341 parameters | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0100 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2019 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.4309 (2) | 0.9455 (5) | 0.37704 (12) | 0.0298 (6) | |
H1 | 0.3981 | 1.0553 | 0.3494 | 0.036* | |
C2 | 0.5462 (2) | 0.9545 (5) | 0.39464 (12) | 0.0285 (6) | |
C3 | 0.5938 (2) | 0.7913 (6) | 0.43555 (12) | 0.0308 (6) | |
C4 | 0.5283 (2) | 0.6235 (6) | 0.45789 (12) | 0.0335 (7) | |
H4 | 0.5609 | 0.5112 | 0.4851 | 0.040* | |
C5 | 0.4134 (2) | 0.6185 (6) | 0.44043 (13) | 0.0343 (7) | |
H5 | 0.3682 | 0.5050 | 0.4566 | 0.041* | |
C6 | 0.3648 (2) | 0.7762 (6) | 0.39998 (12) | 0.0304 (6) | |
O1 | 0.61740 (16) | 1.1130 (4) | 0.37392 (9) | 0.0404 (6) | |
C7 | 0.5687 (3) | 1.2757 (7) | 0.33145 (14) | 0.0447 (8) | |
H7A | 0.5131 | 1.3820 | 0.3449 | 0.067* | |
H7B | 0.5327 | 1.1768 | 0.3008 | 0.067* | |
H7C | 0.6269 | 1.3797 | 0.3196 | 0.067* | |
O2 | 0.70702 (15) | 0.8155 (4) | 0.45125 (8) | 0.0372 (5) | |
C8 | 0.7568 (3) | 0.6385 (7) | 0.49009 (14) | 0.0451 (8) | |
H8A | 0.7439 | 0.4703 | 0.4754 | 0.068* | |
H8B | 0.7237 | 0.6541 | 0.5235 | 0.068* | |
H8C | 0.8371 | 0.6697 | 0.4981 | 0.068* | |
C9 | 0.2409 (2) | 0.7583 (5) | 0.37971 (13) | 0.0302 (6) | |
H9A | 0.2154 | 0.9137 | 0.3605 | 0.036* | |
H9B | 0.1999 | 0.7401 | 0.4110 | 0.036* | |
C10 | 0.2141 (2) | 0.5359 (6) | 0.34114 (12) | 0.0304 (7) | |
H10 | 0.2519 | 0.3858 | 0.3590 | 0.036* | |
C11 | 0.0898 (2) | 0.4842 (5) | 0.33061 (13) | 0.0323 (7) | |
O3 | 0.02860 (18) | 0.5547 (4) | 0.29049 (9) | 0.0436 (6) | |
O4 | 0.05982 (15) | 0.3575 (4) | 0.37208 (8) | 0.0347 (5) | |
C12 | −0.0575 (2) | 0.2753 (6) | 0.37180 (13) | 0.0326 (7) | |
C13 | −0.0935 (3) | 0.1097 (6) | 0.32394 (14) | 0.0417 (8) | |
H13A | −0.0369 | −0.0187 | 0.3220 | 0.062* | |
H13B | −0.1025 | 0.2090 | 0.2906 | 0.062* | |
H13C | −0.1645 | 0.0307 | 0.3280 | 0.062* | |
C14 | −0.1336 (3) | 0.5002 (6) | 0.37261 (15) | 0.0411 (8) | |
H14A | −0.2061 | 0.4462 | 0.3812 | 0.062* | |
H14B | −0.1436 | 0.5806 | 0.3369 | 0.062* | |
H14C | −0.1000 | 0.6184 | 0.4002 | 0.062* | |
C15 | −0.0489 (3) | 0.1367 (7) | 0.42536 (14) | 0.0421 (8) | |
H15A | 0.0057 | 0.0022 | 0.4259 | 0.063* | |
H15B | −0.1217 | 0.0666 | 0.4295 | 0.063* | |
H15C | −0.0251 | 0.2519 | 0.4553 | 0.063* | |
N1 | 0.25893 (19) | 0.5802 (5) | 0.29144 (10) | 0.0337 (6) | |
H1A | 0.2737 | 0.7326 | 0.2818 | 0.040* | |
C16 | 0.2778 (2) | 0.3850 (6) | 0.25989 (13) | 0.0323 (7) | |
O5 | 0.26403 (18) | 0.1684 (4) | 0.27130 (9) | 0.0374 (5) | |
O6 | 0.31859 (18) | 0.4624 (4) | 0.21537 (9) | 0.0395 (5) | |
C17 | 0.3536 (3) | 0.2657 (7) | 0.18178 (14) | 0.0412 (7) | |
H17A | 0.2881 | 0.1900 | 0.1594 | 0.049* | |
H17B | 0.3935 | 0.1344 | 0.2048 | 0.049* | |
C18 | 0.4304 (3) | 0.3820 (6) | 0.14562 (13) | 0.0379 (7) | |
H18 | 0.3898 | 0.5137 | 0.1222 | 0.045* | |
C19 | 0.5373 (3) | 0.4861 (6) | 0.17632 (12) | 0.0358 (7) | |
C20 | 0.5532 (3) | 0.6770 (6) | 0.21357 (13) | 0.0410 (7) | |
H20 | 0.4912 | 0.7614 | 0.2243 | 0.049* | |
C21 | 0.6625 (3) | 0.7450 (7) | 0.23542 (15) | 0.0487 (9) | |
H21 | 0.6745 | 0.8760 | 0.2612 | 0.058* | |
C22 | 0.7523 (3) | 0.6227 (8) | 0.21972 (15) | 0.0511 (9) | |
H22 | 0.8257 | 0.6722 | 0.2344 | 0.061* | |
C23 | 0.7371 (3) | 0.4289 (8) | 0.18282 (14) | 0.0495 (9) | |
H23 | 0.7994 | 0.3430 | 0.1728 | 0.059* | |
C24 | 0.6293 (3) | 0.3613 (6) | 0.16049 (13) | 0.0410 (8) | |
C25 | 0.5887 (3) | 0.1715 (7) | 0.12087 (13) | 0.0428 (8) | |
C26 | 0.6448 (4) | −0.0076 (8) | 0.09507 (15) | 0.0538 (10) | |
H26 | 0.7237 | −0.0170 | 0.1022 | 0.065* | |
C27 | 0.5863 (4) | −0.1702 (8) | 0.05946 (15) | 0.0587 (11) | |
H27 | 0.6251 | −0.2922 | 0.0420 | 0.070* | |
C28 | 0.4713 (4) | −0.1592 (8) | 0.04859 (15) | 0.0593 (11) | |
H28 | 0.4319 | −0.2723 | 0.0235 | 0.071* | |
C29 | 0.4121 (4) | 0.0193 (7) | 0.07465 (15) | 0.0519 (9) | |
H29 | 0.3332 | 0.0271 | 0.0676 | 0.062* | |
C30 | 0.4722 (3) | 0.1827 (7) | 0.11076 (13) | 0.0413 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0237 (13) | 0.0301 (14) | 0.0357 (16) | −0.0012 (11) | 0.0045 (11) | −0.0014 (13) |
C2 | 0.0251 (13) | 0.0270 (14) | 0.0347 (16) | −0.0025 (11) | 0.0081 (11) | 0.0012 (13) |
C3 | 0.0211 (12) | 0.0372 (15) | 0.0337 (16) | 0.0007 (12) | 0.0025 (11) | 0.0024 (14) |
C4 | 0.0284 (14) | 0.0371 (17) | 0.0345 (16) | −0.0009 (13) | 0.0031 (12) | 0.0035 (14) |
C5 | 0.0317 (14) | 0.0329 (16) | 0.0391 (17) | −0.0028 (13) | 0.0078 (12) | 0.0066 (14) |
C6 | 0.0251 (13) | 0.0300 (14) | 0.0369 (17) | −0.0036 (12) | 0.0074 (12) | −0.0028 (13) |
O1 | 0.0311 (10) | 0.0443 (13) | 0.0455 (13) | −0.0051 (10) | 0.0048 (9) | 0.0171 (11) |
C7 | 0.0409 (17) | 0.0470 (19) | 0.046 (2) | −0.0070 (15) | 0.0052 (15) | 0.0204 (17) |
O2 | 0.0234 (9) | 0.0480 (13) | 0.0391 (12) | 0.0018 (9) | 0.0008 (8) | 0.0089 (11) |
C8 | 0.0339 (16) | 0.056 (2) | 0.0432 (19) | 0.0107 (15) | −0.0025 (14) | 0.0077 (18) |
C9 | 0.0203 (12) | 0.0291 (14) | 0.0408 (17) | −0.0033 (11) | 0.0034 (11) | −0.0053 (13) |
C10 | 0.0255 (14) | 0.0298 (14) | 0.0368 (17) | −0.0024 (11) | 0.0077 (12) | −0.0015 (13) |
C11 | 0.0284 (14) | 0.0278 (14) | 0.0417 (18) | −0.0035 (12) | 0.0085 (13) | −0.0016 (14) |
O3 | 0.0328 (11) | 0.0487 (14) | 0.0476 (14) | −0.0015 (10) | 0.0005 (10) | 0.0081 (11) |
O4 | 0.0250 (9) | 0.0372 (11) | 0.0423 (12) | −0.0088 (9) | 0.0064 (8) | 0.0035 (10) |
C12 | 0.0231 (13) | 0.0283 (14) | 0.0466 (18) | −0.0059 (12) | 0.0053 (12) | −0.0004 (14) |
C13 | 0.0433 (17) | 0.0288 (16) | 0.051 (2) | −0.0038 (14) | 0.0023 (15) | −0.0049 (15) |
C14 | 0.0321 (15) | 0.0349 (17) | 0.058 (2) | 0.0006 (13) | 0.0125 (14) | −0.0056 (16) |
C15 | 0.0346 (15) | 0.0414 (17) | 0.051 (2) | −0.0076 (14) | 0.0087 (14) | 0.0076 (16) |
N1 | 0.0339 (13) | 0.0293 (13) | 0.0397 (15) | −0.0043 (11) | 0.0112 (11) | 0.0001 (11) |
C16 | 0.0293 (14) | 0.0346 (15) | 0.0339 (17) | −0.0008 (12) | 0.0072 (12) | −0.0015 (13) |
O5 | 0.0422 (11) | 0.0306 (11) | 0.0400 (13) | −0.0019 (9) | 0.0076 (9) | 0.0011 (10) |
O6 | 0.0467 (12) | 0.0351 (11) | 0.0397 (12) | 0.0041 (10) | 0.0161 (10) | −0.0006 (10) |
C17 | 0.0490 (18) | 0.0376 (16) | 0.0397 (18) | 0.0025 (15) | 0.0151 (15) | −0.0008 (15) |
C18 | 0.0403 (16) | 0.0413 (17) | 0.0327 (17) | 0.0036 (14) | 0.0074 (13) | 0.0020 (14) |
C19 | 0.0423 (17) | 0.0338 (15) | 0.0311 (16) | 0.0021 (13) | 0.0051 (13) | 0.0025 (14) |
C20 | 0.0461 (17) | 0.0360 (17) | 0.0404 (18) | 0.0070 (15) | 0.0041 (14) | 0.0046 (16) |
C21 | 0.0497 (19) | 0.049 (2) | 0.046 (2) | −0.0033 (17) | −0.0005 (16) | 0.0044 (17) |
C22 | 0.0458 (19) | 0.059 (2) | 0.047 (2) | 0.0029 (17) | 0.0020 (16) | 0.0046 (19) |
C23 | 0.0383 (17) | 0.066 (3) | 0.045 (2) | 0.0068 (17) | 0.0076 (15) | 0.0065 (19) |
C24 | 0.0477 (18) | 0.0423 (18) | 0.0348 (17) | 0.0052 (15) | 0.0122 (14) | 0.0026 (15) |
C25 | 0.0534 (19) | 0.0446 (18) | 0.0327 (17) | 0.0079 (16) | 0.0137 (15) | 0.0076 (16) |
C26 | 0.069 (2) | 0.054 (2) | 0.044 (2) | 0.0146 (19) | 0.0249 (18) | 0.0028 (19) |
C27 | 0.092 (3) | 0.048 (2) | 0.042 (2) | 0.008 (2) | 0.028 (2) | −0.0015 (18) |
C28 | 0.097 (3) | 0.050 (2) | 0.033 (2) | −0.005 (2) | 0.019 (2) | −0.0056 (18) |
C29 | 0.070 (2) | 0.049 (2) | 0.0386 (19) | −0.0066 (18) | 0.0129 (17) | 0.0024 (17) |
C30 | 0.0513 (18) | 0.0413 (17) | 0.0324 (17) | −0.0013 (16) | 0.0102 (14) | 0.0016 (15) |
Geometric parameters (Å, º) top
C1—H1 | 0.950 | C14—H14C | 0.980 |
C1—C2 | 1.405 (4) | C15—H15A | 0.980 |
C1—C6 | 1.391 (4) | C15—H15B | 0.980 |
C2—C3 | 1.404 (4) | C15—H15C | 0.980 |
C2—O1 | 1.368 (3) | N1—H1A | 0.880 |
C3—C4 | 1.373 (4) | N1—C16 | 1.352 (4) |
C3—O2 | 1.380 (3) | C16—O5 | 1.216 (4) |
C4—H4 | 0.950 | C16—O6 | 1.346 (4) |
C4—C5 | 1.399 (4) | O6—C17 | 1.451 (4) |
C5—H5 | 0.950 | C17—H17A | 0.990 |
C5—C6 | 1.382 (4) | C17—H17B | 0.990 |
C6—C9 | 1.518 (4) | C17—C18 | 1.523 (4) |
O1—C7 | 1.433 (4) | C18—H18 | 1.000 |
C7—H7A | 0.980 | C18—C19 | 1.514 (4) |
C7—H7B | 0.980 | C18—C30 | 1.514 (5) |
C7—H7C | 0.980 | C19—C20 | 1.378 (5) |
O2—C8 | 1.427 (4) | C19—C24 | 1.409 (4) |
C8—H8A | 0.980 | C20—H20 | 0.950 |
C8—H8B | 0.980 | C20—C21 | 1.408 (5) |
C8—H8C | 0.980 | C21—H21 | 0.950 |
C9—H9A | 0.990 | C21—C22 | 1.379 (5) |
C9—H9B | 0.990 | C22—H22 | 0.950 |
C9—C10 | 1.539 (4) | C22—C23 | 1.384 (6) |
C10—H10 | 1.000 | C23—H23 | 0.950 |
C10—C11 | 1.519 (4) | C23—C24 | 1.393 (5) |
C10—N1 | 1.444 (4) | C24—C25 | 1.455 (5) |
C11—O3 | 1.216 (4) | C25—C26 | 1.391 (5) |
C11—O4 | 1.333 (4) | C25—C30 | 1.401 (5) |
O4—C12 | 1.491 (3) | C26—H26 | 0.950 |
C12—C13 | 1.501 (4) | C26—C27 | 1.368 (6) |
C12—C14 | 1.523 (4) | C27—H27 | 0.950 |
C12—C15 | 1.519 (5) | C27—C28 | 1.384 (6) |
C13—H13A | 0.980 | C28—H28 | 0.950 |
C13—H13B | 0.980 | C28—C29 | 1.413 (6) |
C13—H13C | 0.980 | C29—H29 | 0.950 |
C14—H14A | 0.980 | C29—C30 | 1.386 (5) |
C14—H14B | 0.980 | ||
H1—C1—C2 | 119.9 | H14A—C14—H14C | 109.5 |
H1—C1—C6 | 119.9 | H14B—C14—H14C | 109.5 |
C2—C1—C6 | 120.2 (3) | C12—C15—H15A | 109.5 |
C1—C2—C3 | 119.3 (2) | C12—C15—H15B | 109.5 |
C1—C2—O1 | 124.0 (3) | C12—C15—H15C | 109.5 |
C3—C2—O1 | 116.6 (2) | H15A—C15—H15B | 109.5 |
C2—C3—C4 | 120.3 (2) | H15A—C15—H15C | 109.5 |
C2—C3—O2 | 115.7 (2) | H15B—C15—H15C | 109.5 |
C4—C3—O2 | 124.0 (3) | C10—N1—H1A | 120.4 |
C3—C4—H4 | 120.1 | C10—N1—C16 | 119.2 (2) |
C3—C4—C5 | 119.7 (3) | H1A—N1—C16 | 120.4 |
H4—C4—C5 | 120.1 | N1—C16—O5 | 124.5 (3) |
C4—C5—H5 | 119.5 | N1—C16—O6 | 110.7 (3) |
C4—C5—C6 | 121.0 (3) | O5—C16—O6 | 124.7 (3) |
H5—C5—C6 | 119.5 | C16—O6—C17 | 115.1 (2) |
C1—C6—C5 | 119.4 (3) | O6—C17—H17A | 110.2 |
C1—C6—C9 | 120.6 (3) | O6—C17—H17B | 110.2 |
C5—C6—C9 | 120.0 (3) | O6—C17—C18 | 107.4 (3) |
C2—O1—C7 | 116.4 (2) | H17A—C17—H17B | 108.5 |
O1—C7—H7A | 109.5 | H17A—C17—C18 | 110.2 |
O1—C7—H7B | 109.5 | H17B—C17—C18 | 110.2 |
O1—C7—H7C | 109.5 | C17—C18—H18 | 110.2 |
H7A—C7—H7B | 109.5 | C17—C18—C19 | 114.0 (3) |
H7A—C7—H7C | 109.5 | C17—C18—C30 | 109.6 (3) |
H7B—C7—H7C | 109.5 | H18—C18—C19 | 110.2 |
C3—O2—C8 | 115.8 (2) | H18—C18—C30 | 110.2 |
O2—C8—H8A | 109.5 | C19—C18—C30 | 102.5 (3) |
O2—C8—H8B | 109.5 | C18—C19—C20 | 129.9 (3) |
O2—C8—H8C | 109.5 | C18—C19—C24 | 109.8 (3) |
H8A—C8—H8B | 109.5 | C20—C19—C24 | 120.3 (3) |
H8A—C8—H8C | 109.5 | C19—C20—H20 | 120.5 |
H8B—C8—H8C | 109.5 | C19—C20—C21 | 119.0 (3) |
C6—C9—H9A | 109.3 | H20—C20—C21 | 120.5 |
C6—C9—H9B | 109.3 | C20—C21—H21 | 119.8 |
C6—C9—C10 | 111.4 (2) | C20—C21—C22 | 120.5 (4) |
H9A—C9—H9B | 108.0 | H21—C21—C22 | 119.8 |
H9A—C9—C10 | 109.3 | C21—C22—H22 | 119.6 |
H9B—C9—C10 | 109.3 | C21—C22—C23 | 120.9 (3) |
C9—C10—H10 | 108.0 | H22—C22—C23 | 119.6 |
C9—C10—C11 | 111.3 (2) | C22—C23—H23 | 120.4 |
C9—C10—N1 | 109.6 (2) | C22—C23—C24 | 119.2 (3) |
H10—C10—C11 | 108.0 | H23—C23—C24 | 120.4 |
H10—C10—N1 | 108.0 | C19—C24—C23 | 120.1 (3) |
C11—C10—N1 | 111.8 (2) | C19—C24—C25 | 108.7 (3) |
C10—C11—O3 | 123.9 (3) | C23—C24—C25 | 131.3 (3) |
C10—C11—O4 | 109.7 (2) | C24—C25—C26 | 131.2 (3) |
O3—C11—O4 | 126.4 (3) | C24—C25—C30 | 109.0 (3) |
C11—O4—C12 | 121.2 (2) | C26—C25—C30 | 119.8 (4) |
O4—C12—C13 | 110.2 (2) | C25—C26—H26 | 120.0 |
O4—C12—C14 | 110.2 (2) | C25—C26—C27 | 120.0 (4) |
O4—C12—C15 | 101.4 (2) | H26—C26—C27 | 120.0 |
C13—C12—C14 | 112.0 (3) | C26—C27—H27 | 119.6 |
C13—C12—C15 | 112.4 (3) | C26—C27—C28 | 120.8 (4) |
C14—C12—C15 | 110.0 (3) | H27—C27—C28 | 119.6 |
C12—C13—H13A | 109.5 | C27—C28—H28 | 119.8 |
C12—C13—H13B | 109.5 | C27—C28—C29 | 120.3 (4) |
C12—C13—H13C | 109.5 | H28—C28—C29 | 119.8 |
H13A—C13—H13B | 109.5 | C28—C29—H29 | 120.8 |
H13A—C13—H13C | 109.5 | C28—C29—C30 | 118.4 (4) |
H13B—C13—H13C | 109.5 | H29—C29—C30 | 120.8 |
C12—C14—H14A | 109.5 | C18—C30—C25 | 110.0 (3) |
C12—C14—H14B | 109.5 | C18—C30—C29 | 129.3 (3) |
C12—C14—H14C | 109.5 | C25—C30—C29 | 120.7 (3) |
H14A—C14—H14B | 109.5 | ||
C6—C1—C2—C3 | 0.0 (4) | O6—C17—C18—C19 | 64.1 (3) |
C6—C1—C2—O1 | 179.3 (3) | O6—C17—C18—C30 | 178.4 (3) |
C1—C2—C3—C4 | 0.4 (4) | C17—C18—C19—C20 | −63.2 (4) |
C1—C2—C3—O2 | −178.8 (3) | C17—C18—C19—C24 | 118.6 (3) |
O1—C2—C3—C4 | −178.9 (3) | C30—C18—C19—C20 | 178.4 (3) |
O1—C2—C3—O2 | 1.9 (4) | C30—C18—C19—C24 | 0.3 (3) |
C2—C3—C4—C5 | −1.2 (5) | C18—C19—C20—C21 | −177.9 (3) |
O2—C3—C4—C5 | 177.9 (3) | C24—C19—C20—C21 | 0.0 (5) |
C3—C4—C5—C6 | 1.6 (5) | C19—C20—C21—C22 | 0.1 (5) |
C4—C5—C6—C1 | −1.2 (5) | C20—C21—C22—C23 | −0.9 (6) |
C4—C5—C6—C9 | 176.9 (3) | C21—C22—C23—C24 | 1.5 (5) |
C2—C1—C6—C5 | 0.4 (4) | C22—C23—C24—C19 | −1.3 (5) |
C2—C1—C6—C9 | −177.6 (3) | C22—C23—C24—C25 | 178.9 (3) |
C1—C2—O1—C7 | −0.5 (4) | C18—C19—C24—C23 | 178.9 (3) |
C3—C2—O1—C7 | 178.8 (3) | C18—C19—C24—C25 | −1.3 (4) |
C2—C3—O2—C8 | −175.8 (3) | C20—C19—C24—C23 | 0.6 (5) |
C4—C3—O2—C8 | 5.1 (4) | C20—C19—C24—C25 | −179.6 (3) |
C1—C6—C9—C10 | 100.6 (3) | C19—C24—C25—C26 | −176.5 (3) |
C5—C6—C9—C10 | −77.4 (3) | C19—C24—C25—C30 | 1.8 (4) |
C6—C9—C10—C11 | 167.7 (3) | C23—C24—C25—C26 | 3.4 (6) |
C6—C9—C10—N1 | −68.1 (3) | C23—C24—C25—C30 | −178.4 (4) |
C9—C10—C11—O3 | 98.7 (3) | C24—C25—C26—C27 | 178.9 (4) |
C9—C10—C11—O4 | −80.0 (3) | C30—C25—C26—C27 | 0.8 (5) |
N1—C10—C11—O3 | −24.3 (4) | C25—C26—C27—C28 | 0.0 (6) |
N1—C10—C11—O4 | 157.1 (2) | C26—C27—C28—C29 | −0.7 (6) |
C10—C11—O4—C12 | −178.3 (2) | C27—C28—C29—C30 | 0.5 (5) |
O3—C11—O4—C12 | 3.1 (5) | C28—C29—C30—C18 | −177.1 (3) |
C11—O4—C12—C13 | 59.2 (3) | C28—C29—C30—C25 | 0.3 (5) |
C11—O4—C12—C14 | −65.0 (3) | C24—C25—C30—C18 | −1.6 (4) |
C11—O4—C12—C15 | 178.5 (3) | C24—C25—C30—C29 | −179.4 (3) |
C9—C10—N1—C16 | 158.5 (2) | C26—C25—C30—C18 | 176.9 (3) |
C11—C10—N1—C16 | −77.5 (3) | C26—C25—C30—C29 | −0.9 (5) |
C10—N1—C16—O5 | −3.2 (4) | C17—C18—C30—C25 | −120.6 (3) |
C10—N1—C16—O6 | 179.5 (2) | C17—C18—C30—C29 | 57.0 (4) |
N1—C16—O6—C17 | 173.3 (2) | C19—C18—C30—C25 | 0.8 (3) |
O5—C16—O6—C17 | −3.9 (4) | C19—C18—C30—C29 | 178.4 (3) |
C16—O6—C17—C18 | −161.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O5i | 0.88 | 2.36 | 3.204 (3) | 161 |
C1—H1···O5i | 0.95 | 2.42 | 3.305 (4) | 154 |
Symmetry code: (i) x, y+1, z. |