The title compound, C
30H
33NO
6·1.5CHCl
3, a derivative of
L-DOPA, forms chains in its crystal structure,
via weak N—H
O=C hydrogen bonds involving the carbamate N—H and carbonyl groups of adjacent molecules, supported by N—H
O=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
CCDC reference: 227890
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.005 Å
Some non-H atoms missing
- R factor = 0.053
- wR factor = 0.153
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level A
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.90 <> 1.10
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_weight 682.63
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 30.00 360.33
H 1.01 33.00 33.26
N 14.01 1.00 14.01
O 16.00 6.00 95.99
Cl 35.45 0.00 0.00
Calculated formula weight 503.59
| Author Response: The quoted formula includes disordered solvent modelled
by PLATON/SQUEEZE and not part of the atom list
|
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: The data coverage at the highest values of theta (>55 degrees)
is incomplete because of mechanical restrictions of the low-temperature
device
|
PLAT043_ALERT_1_A Check Reported Molecular Weight ................ 682.63
| Author Response: The quoted formula includes disordered solvent modelled
by PLATON/SQUEEZE and not part of the atom list
|
PLAT044_ALERT_1_A Calculated and Reported Dx Differ .............. ?
| Author Response: The quoted formula includes disordered solvent modelled
by PLATON/SQUEEZE and not part of the atom list
|
PLAT051_ALERT_1_A Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 85.68 Perc.
| Author Response: The quoted formula includes disordered solvent modelled
by PLATON/SQUEEZE and not part of the atom list
|
Alert level C
RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 1.54175-1.54180
Wavelength given = 1.54184
PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High .... 0.30
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.13
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure !
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C31.5 H34.5 Cl4.5 N1 O6
Atom count from the _atom_site data: C30 H33 N1 O6
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
symmetry error - see SYMMG tests
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C31.50 H34.50 Cl4.50 N O6
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 63.00 60.00 3.00
H 69.00 66.00 3.00
Cl 9.00 0.00 9.00
N 2.00 2.00 0.00
O 12.00 12.00 0.00
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 67.21
From the CIF: _reflns_number_total 5020
Count of symmetry unique reflns 3235
Completeness (_total/calc) 155.18%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1785
Fraction of Friedel pairs measured 0.552
Are heavy atom types Z>Si present no
5 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
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.
(2
S)-2-(9
H-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. |