The title compound, C17H29NO6, crystallizes with two molecules in the asymmetric unit. The independent molecules differ in the conformation of the side chain attached to nitrogen. The piperidine ring adopts a chair conformation, with the 1,3-dioxolane ring occupying an axial position.
Supporting information
CCDC reference: 189899
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.049
- wR factor = 0.119
- Data-to-parameter ratio = 7.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 3277
Count of symmetry unique reflns 3288
Completeness (_total/calc) 99.67%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
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.
Data collection: XSCANS (Siemens, 1993); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1989); software used to prepare material for publication: SHELXL97.
tert-Butyl
(7
R)-7-[(4
S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1,4-dioxa-8-
azaspiro[4.5]decane-8-carboxylate
top
Crystal data top
C17H29NO6 | Z = 2 |
Mr = 343.41 | F(000) = 372 |
Triclinic, P1 | Dx = 1.220 Mg m−3 |
a = 9.641 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.997 (1) Å | Cell parameters from 38 reflections |
c = 11.042 (1) Å | θ = 7.2–12.5° |
α = 84.77 (1)° | µ = 0.09 mm−1 |
β = 69.72 (1)° | T = 293 K |
γ = 69.59 (1)° | Block, colourless |
V = 935.1 (2) Å3 | 0.44 × 0.32 × 0.28 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = −1→11 |
ω–2θ scans | k = −11→11 |
3913 measured reflections | l = −12→13 |
3277 independent reflections | 3 standard reflections every 97 reflections |
2068 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1664P] where P = (Fo2 + 2Fc2)/3 |
3277 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.15 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O12 | 0.7843 (4) | 0.0217 (3) | 0.4476 (3) | 0.0510 (9) | |
O9 | 0.6570 (4) | 0.1932 (3) | 0.8085 (3) | 0.0578 (10) | |
O11 | 0.5675 (4) | 0.2178 (4) | 0.5191 (3) | 0.0552 (9) | |
O6 | 0.5119 (4) | 0.7777 (4) | 1.1066 (3) | 0.0557 (10) | |
O5 | 0.4772 (4) | 0.7878 (4) | 0.9121 (4) | 0.0607 (10) | |
O8 | 1.0340 (4) | 0.3510 (4) | 0.6366 (3) | 0.0591 (10) | |
O10 | 0.4529 (4) | 0.3990 (4) | 0.8835 (3) | 0.0586 (10) | |
O3 | 0.8208 (4) | 0.4724 (4) | 1.0300 (4) | 0.0650 (11) | |
O1 | 1.1256 (4) | 0.6881 (4) | 0.7640 (3) | 0.0608 (10) | |
N2 | 0.7967 (4) | 0.2017 (4) | 0.5434 (4) | 0.0446 (10) | |
N1 | 0.7187 (4) | 0.7437 (4) | 0.9261 (4) | 0.0415 (10) | |
O2 | 1.0625 (5) | 0.9282 (4) | 0.7885 (4) | 0.0722 (12) | |
O7 | 1.0679 (5) | 0.4641 (4) | 0.4481 (4) | 0.0764 (12) | |
O4 | 1.0285 (5) | 0.3622 (4) | 1.0990 (4) | 0.0826 (13) | |
C13 | 0.5622 (6) | 0.7698 (5) | 0.9752 (5) | 0.0449 (13) | |
C30 | 0.7037 (6) | 0.1536 (5) | 0.5055 (4) | 0.0426 (12) | |
C24 | 0.7273 (6) | 0.3347 (5) | 0.6198 (5) | 0.0439 (12) | |
H24 | 0.6201 | 0.3806 | 0.6182 | 0.053* | |
C7 | 0.8252 (5) | 0.7108 (5) | 1.0001 (4) | 0.0404 (12) | |
H7 | 0.7611 | 0.7317 | 1.0915 | 0.048* | |
C20 | 0.9941 (6) | 0.3691 (5) | 0.5228 (5) | 0.0512 (13) | |
C18 | 0.9646 (6) | 0.1287 (5) | 0.5193 (5) | 0.0491 (13) | |
H18A | 1.0009 | 0.0421 | 0.4674 | 0.059* | |
H18B | 0.9828 | 0.1023 | 0.6007 | 0.059* | |
C1 | 0.7936 (6) | 0.7380 (5) | 0.7851 (4) | 0.0473 (13) | |
H1A | 0.7140 | 0.7620 | 0.7443 | 0.057* | |
H1B | 0.8653 | 0.6420 | 0.7563 | 0.057* | |
C6 | 0.9238 (6) | 0.8088 (5) | 0.9606 (5) | 0.0481 (13) | |
H6A | 1.0070 | 0.7748 | 0.9978 | 0.058* | |
H6B | 0.8577 | 0.9040 | 0.9967 | 0.058* | |
C3 | 0.9975 (6) | 0.8177 (5) | 0.8144 (5) | 0.0484 (13) | |
C31 | 0.7032 (6) | −0.0572 (6) | 0.4082 (5) | 0.0506 (13) | |
C25 | 0.7166 (6) | 0.3069 (5) | 0.7604 (5) | 0.0467 (13) | |
H25 | 0.8195 | 0.2861 | 0.7697 | 0.056* | |
C23 | 0.8204 (6) | 0.4349 (5) | 0.5562 (5) | 0.0507 (14) | |
H23A | 0.7976 | 0.4697 | 0.4779 | 0.061* | |
H23B | 0.7835 | 0.5168 | 0.6142 | 0.061* | |
C19 | 1.0561 (6) | 0.2269 (5) | 0.4486 (5) | 0.0545 (14) | |
H19A | 1.1665 | 0.1804 | 0.4382 | 0.065* | |
H19B | 1.0472 | 0.2442 | 0.3633 | 0.065* | |
C2 | 0.8826 (6) | 0.8416 (5) | 0.7458 (5) | 0.0498 (14) | |
H2A | 0.9382 | 0.8313 | 0.6534 | 0.060* | |
H2B | 0.8086 | 0.9384 | 0.7648 | 0.060* | |
C8 | 0.9246 (6) | 0.5521 (5) | 0.9850 (5) | 0.0448 (12) | |
H8 | 0.9899 | 0.5262 | 0.8944 | 0.054* | |
C9 | 1.0245 (6) | 0.5048 (5) | 1.0713 (5) | 0.0557 (14) | |
H9A | 1.1294 | 0.5082 | 1.0269 | 0.067* | |
H9B | 0.9769 | 0.5642 | 1.1497 | 0.067* | |
C27 | 0.4982 (6) | 0.2480 (6) | 0.8954 (5) | 0.0538 (14) | |
C26 | 0.5925 (6) | 0.4325 (5) | 0.8513 (5) | 0.0564 (15) | |
H26A | 0.6186 | 0.4378 | 0.9277 | 0.068* | |
H26B | 0.5825 | 0.5225 | 0.8079 | 0.068* | |
C10 | 0.8896 (7) | 0.3483 (6) | 1.0901 (6) | 0.0622 (16) | |
C32 | 0.6442 (9) | 0.0172 (6) | 0.3020 (5) | 0.0764 (19) | |
H32A | 0.5643 | 0.1077 | 0.3345 | 0.115* | |
H32B | 0.6008 | −0.0407 | 0.2718 | 0.115* | |
H32C | 0.7296 | 0.0320 | 0.2320 | 0.115* | |
C14 | 0.3486 (6) | 0.7874 (6) | 1.1817 (5) | 0.0563 (15) | |
C33 | 0.5702 (7) | −0.0770 (7) | 0.5246 (5) | 0.0689 (17) | |
H33A | 0.4909 | 0.0143 | 0.5551 | 0.103* | |
H33B | 0.6109 | −0.1204 | 0.5921 | 0.103* | |
H33C | 0.5252 | −0.1374 | 0.5000 | 0.103* | |
C28 | 0.3971 (7) | 0.1943 (6) | 0.8502 (6) | 0.0695 (17) | |
H28A | 0.4266 | 0.0926 | 0.8582 | 0.104* | |
H28B | 0.4108 | 0.2174 | 0.7615 | 0.104* | |
H28C | 0.2889 | 0.2385 | 0.9021 | 0.104* | |
C34 | 0.8286 (8) | −0.1985 (6) | 0.3602 (7) | 0.085 (2) | |
H34A | 0.8649 | −0.2441 | 0.4292 | 0.128* | |
H34B | 0.9148 | −0.1842 | 0.2906 | 0.128* | |
H34C | 0.7866 | −0.2577 | 0.3301 | 0.128* | |
C22 | 1.1862 (7) | 0.3637 (7) | 0.6017 (6) | 0.0718 (18) | |
H22A | 1.2682 | 0.2708 | 0.5820 | 0.086* | |
H22B | 1.1947 | 0.4110 | 0.6705 | 0.086* | |
C15 | 0.2347 (7) | 0.9240 (6) | 1.1580 (7) | 0.086 (2) | |
H15A | 0.2375 | 0.9236 | 1.0703 | 0.128* | |
H15B | 0.2627 | 1.0027 | 1.1729 | 0.128* | |
H15C | 0.1307 | 0.9337 | 1.2156 | 0.128* | |
C29 | 0.4928 (8) | 0.2072 (7) | 1.0303 (6) | 0.082 (2) | |
H29A | 0.5235 | 0.1052 | 1.0359 | 0.123* | |
H29B | 0.3879 | 0.2503 | 1.0890 | 0.123* | |
H29C | 0.5637 | 0.2399 | 1.0526 | 0.123* | |
C16 | 0.3503 (8) | 0.7822 (8) | 1.3187 (6) | 0.084 (2) | |
H16A | 0.4253 | 0.6933 | 1.3300 | 0.126* | |
H16B | 0.2477 | 0.7900 | 1.3782 | 0.126* | |
H16C | 0.3792 | 0.8599 | 1.3348 | 0.126* | |
C11 | 0.9386 (9) | 0.2180 (7) | 1.0082 (8) | 0.099 (2) | |
H11A | 0.9848 | 0.1351 | 1.0507 | 0.149* | |
H11B | 1.0141 | 0.2250 | 0.9263 | 0.149* | |
H11C | 0.8483 | 0.2102 | 0.9951 | 0.149* | |
C17 | 0.3209 (8) | 0.6550 (6) | 1.1503 (6) | 0.0774 (19) | |
H17A | 0.3976 | 0.5707 | 1.1669 | 0.116* | |
H17B | 0.3301 | 0.6542 | 1.0610 | 0.116* | |
H17C | 0.2174 | 0.6570 | 1.2035 | 0.116* | |
C4 | 1.2642 (8) | 0.7155 (9) | 0.7451 (8) | 0.095 (2) | |
H4A | 1.3426 | 0.6738 | 0.6629 | 0.114* | |
H4B | 1.3064 | 0.6752 | 0.8134 | 0.114* | |
C5 | 1.2233 (9) | 0.8694 (9) | 0.7465 (9) | 0.107 (3) | |
H5A | 1.2646 | 0.8989 | 0.8041 | 0.129* | |
H5B | 1.2676 | 0.9008 | 0.6605 | 0.129* | |
C12 | 0.7706 (11) | 0.3471 (10) | 1.2206 (6) | 0.122 (3) | |
H12A | 0.8124 | 0.2639 | 1.2649 | 0.183* | |
H12B | 0.6764 | 0.3452 | 1.2103 | 0.183* | |
H12C | 0.7469 | 0.4313 | 1.2699 | 0.183* | |
C21 | 1.1963 (9) | 0.4528 (9) | 0.4837 (8) | 0.100 (2) | |
H21A | 1.1935 | 0.5467 | 0.5029 | 0.121* | |
H21B | 1.2936 | 0.4076 | 0.4142 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O12 | 0.045 (2) | 0.055 (2) | 0.057 (2) | −0.0210 (18) | −0.0134 (18) | −0.0167 (17) |
O9 | 0.048 (2) | 0.0395 (19) | 0.068 (3) | −0.0086 (18) | −0.005 (2) | 0.0018 (17) |
O11 | 0.040 (2) | 0.064 (2) | 0.065 (2) | −0.0135 (19) | −0.0227 (19) | −0.0115 (18) |
O6 | 0.041 (2) | 0.077 (2) | 0.051 (2) | −0.0262 (19) | −0.0089 (18) | −0.0065 (18) |
O5 | 0.045 (2) | 0.076 (3) | 0.066 (3) | −0.019 (2) | −0.025 (2) | −0.004 (2) |
O8 | 0.056 (2) | 0.071 (2) | 0.064 (2) | −0.032 (2) | −0.027 (2) | 0.006 (2) |
O10 | 0.045 (2) | 0.048 (2) | 0.069 (3) | −0.0058 (19) | −0.0097 (19) | −0.0113 (18) |
O3 | 0.072 (3) | 0.060 (2) | 0.093 (3) | −0.038 (2) | −0.056 (2) | 0.034 (2) |
O1 | 0.043 (2) | 0.060 (2) | 0.068 (2) | −0.014 (2) | −0.0074 (19) | −0.0001 (19) |
N2 | 0.035 (2) | 0.041 (2) | 0.056 (3) | −0.010 (2) | −0.014 (2) | −0.012 (2) |
N1 | 0.032 (2) | 0.051 (2) | 0.041 (2) | −0.014 (2) | −0.011 (2) | 0.0019 (19) |
O2 | 0.064 (3) | 0.060 (2) | 0.098 (3) | −0.039 (2) | −0.020 (2) | 0.016 (2) |
O7 | 0.084 (3) | 0.077 (3) | 0.084 (3) | −0.050 (3) | −0.034 (3) | 0.037 (2) |
O4 | 0.087 (3) | 0.080 (3) | 0.116 (4) | −0.042 (3) | −0.072 (3) | 0.039 (3) |
C13 | 0.046 (3) | 0.036 (3) | 0.052 (4) | −0.017 (3) | −0.012 (3) | −0.004 (2) |
C30 | 0.045 (3) | 0.046 (3) | 0.036 (3) | −0.021 (3) | −0.005 (2) | −0.004 (2) |
C24 | 0.035 (3) | 0.035 (3) | 0.059 (3) | −0.006 (2) | −0.017 (3) | −0.007 (2) |
C7 | 0.036 (3) | 0.053 (3) | 0.034 (3) | −0.020 (3) | −0.009 (2) | −0.001 (2) |
C20 | 0.056 (4) | 0.049 (3) | 0.060 (3) | −0.029 (3) | −0.025 (3) | 0.012 (3) |
C18 | 0.041 (3) | 0.041 (3) | 0.064 (3) | −0.012 (3) | −0.015 (3) | −0.008 (3) |
C1 | 0.052 (3) | 0.053 (3) | 0.038 (3) | −0.016 (3) | −0.019 (3) | 0.007 (2) |
C6 | 0.039 (3) | 0.044 (3) | 0.058 (3) | −0.015 (2) | −0.010 (3) | −0.005 (2) |
C3 | 0.050 (3) | 0.037 (3) | 0.059 (4) | −0.021 (3) | −0.013 (3) | 0.002 (2) |
C31 | 0.054 (3) | 0.056 (3) | 0.049 (3) | −0.030 (3) | −0.013 (3) | −0.006 (3) |
C25 | 0.040 (3) | 0.047 (3) | 0.053 (3) | −0.012 (3) | −0.016 (3) | −0.003 (2) |
C23 | 0.059 (4) | 0.039 (3) | 0.059 (3) | −0.015 (3) | −0.029 (3) | 0.005 (2) |
C19 | 0.044 (3) | 0.062 (3) | 0.059 (3) | −0.021 (3) | −0.018 (3) | 0.004 (3) |
C2 | 0.050 (3) | 0.046 (3) | 0.051 (3) | −0.016 (3) | −0.015 (3) | 0.007 (2) |
C8 | 0.049 (3) | 0.044 (3) | 0.050 (3) | −0.024 (3) | −0.019 (3) | 0.006 (2) |
C9 | 0.054 (3) | 0.053 (3) | 0.070 (4) | −0.022 (3) | −0.029 (3) | 0.005 (3) |
C27 | 0.043 (3) | 0.053 (3) | 0.057 (4) | −0.009 (3) | −0.012 (3) | −0.004 (3) |
C26 | 0.054 (4) | 0.048 (3) | 0.064 (4) | −0.013 (3) | −0.016 (3) | −0.015 (3) |
C10 | 0.074 (4) | 0.066 (4) | 0.070 (4) | −0.040 (3) | −0.042 (4) | 0.025 (3) |
C32 | 0.117 (6) | 0.083 (4) | 0.058 (4) | −0.060 (4) | −0.041 (4) | 0.015 (3) |
C14 | 0.039 (3) | 0.063 (4) | 0.062 (4) | −0.022 (3) | −0.001 (3) | −0.015 (3) |
C33 | 0.090 (5) | 0.078 (4) | 0.052 (4) | −0.048 (4) | −0.022 (3) | 0.009 (3) |
C28 | 0.060 (4) | 0.076 (4) | 0.073 (4) | −0.026 (3) | −0.018 (3) | −0.006 (3) |
C34 | 0.077 (5) | 0.065 (4) | 0.106 (5) | −0.022 (4) | −0.015 (4) | −0.036 (4) |
C22 | 0.050 (4) | 0.089 (5) | 0.087 (5) | −0.031 (4) | −0.027 (3) | −0.006 (4) |
C15 | 0.050 (4) | 0.071 (4) | 0.106 (5) | −0.002 (4) | −0.006 (4) | −0.012 (4) |
C29 | 0.084 (5) | 0.088 (5) | 0.064 (4) | −0.022 (4) | −0.021 (4) | 0.008 (3) |
C16 | 0.072 (4) | 0.126 (5) | 0.056 (4) | −0.050 (4) | −0.003 (3) | −0.017 (4) |
C11 | 0.104 (6) | 0.061 (4) | 0.146 (7) | −0.013 (4) | −0.073 (5) | 0.004 (4) |
C17 | 0.074 (4) | 0.082 (4) | 0.077 (4) | −0.042 (4) | −0.005 (4) | −0.018 (3) |
C4 | 0.052 (4) | 0.115 (6) | 0.117 (6) | −0.031 (4) | −0.028 (4) | 0.012 (5) |
C5 | 0.068 (5) | 0.118 (7) | 0.150 (7) | −0.051 (5) | −0.040 (5) | 0.031 (6) |
C12 | 0.148 (8) | 0.186 (9) | 0.067 (5) | −0.112 (7) | −0.030 (5) | 0.035 (5) |
C21 | 0.090 (6) | 0.122 (6) | 0.110 (6) | −0.070 (5) | −0.028 (5) | 0.025 (5) |
Geometric parameters (Å, º) top
O12—C30 | 1.358 (5) | C2—H2A | 0.9700 |
O12—C31 | 1.467 (6) | C2—H2B | 0.9700 |
O9—C25 | 1.427 (6) | C8—C9 | 1.515 (7) |
O9—C27 | 1.434 (6) | C8—H8 | 0.9800 |
O11—C30 | 1.205 (6) | C9—H9A | 0.9700 |
O6—C13 | 1.362 (6) | C9—H9B | 0.9700 |
O6—C14 | 1.476 (6) | C27—C29 | 1.496 (8) |
O5—C13 | 1.207 (6) | C27—C28 | 1.496 (8) |
O8—C20 | 1.416 (6) | C26—H26A | 0.9700 |
O8—C22 | 1.431 (6) | C26—H26B | 0.9700 |
O10—C26 | 1.418 (6) | C10—C11 | 1.492 (8) |
O10—C27 | 1.426 (6) | C10—C12 | 1.500 (9) |
O3—C10 | 1.415 (6) | C32—H32A | 0.9600 |
O3—C8 | 1.422 (6) | C32—H32B | 0.9600 |
O1—C4 | 1.399 (7) | C32—H32C | 0.9600 |
O1—C3 | 1.433 (6) | C14—C15 | 1.493 (8) |
N2—C30 | 1.345 (6) | C14—C16 | 1.515 (8) |
N2—C24 | 1.456 (5) | C14—C17 | 1.529 (7) |
N2—C18 | 1.462 (6) | C33—H33A | 0.9600 |
N1—C13 | 1.350 (6) | C33—H33B | 0.9600 |
N1—C7 | 1.458 (6) | C33—H33C | 0.9600 |
N1—C1 | 1.469 (6) | C28—H28A | 0.9600 |
O2—C5 | 1.371 (7) | C28—H28B | 0.9600 |
O2—C3 | 1.413 (6) | C28—H28C | 0.9600 |
O7—C21 | 1.390 (8) | C34—H34A | 0.9600 |
O7—C20 | 1.417 (6) | C34—H34B | 0.9600 |
O4—C9 | 1.421 (6) | C34—H34C | 0.9600 |
O4—C10 | 1.429 (7) | C22—C21 | 1.504 (9) |
C24—C25 | 1.526 (7) | C22—H22A | 0.9700 |
C24—C23 | 1.538 (7) | C22—H22B | 0.9700 |
C24—H24 | 0.9800 | C15—H15A | 0.9600 |
C7—C6 | 1.528 (6) | C15—H15B | 0.9600 |
C7—C8 | 1.530 (6) | C15—H15C | 0.9600 |
C7—H7 | 0.9800 | C29—H29A | 0.9600 |
C20—C23 | 1.490 (7) | C29—H29B | 0.9600 |
C20—C19 | 1.526 (7) | C29—H29C | 0.9600 |
C18—C19 | 1.529 (7) | C16—H16A | 0.9600 |
C18—H18A | 0.9700 | C16—H16B | 0.9600 |
C18—H18B | 0.9700 | C16—H16C | 0.9600 |
C1—C2 | 1.509 (6) | C11—H11A | 0.9600 |
C1—H1A | 0.9700 | C11—H11B | 0.9600 |
C1—H1B | 0.9700 | C11—H11C | 0.9600 |
C6—C3 | 1.531 (7) | C17—H17A | 0.9600 |
C6—H6A | 0.9700 | C17—H17B | 0.9600 |
C6—H6B | 0.9700 | C17—H17C | 0.9600 |
C3—C2 | 1.490 (7) | C4—C5 | 1.449 (10) |
C31—C34 | 1.496 (7) | C4—H4A | 0.9700 |
C31—C32 | 1.503 (7) | C4—H4B | 0.9700 |
C31—C33 | 1.525 (7) | C5—H5A | 0.9700 |
C25—C26 | 1.538 (7) | C5—H5B | 0.9700 |
C25—H25 | 0.9800 | C12—H12A | 0.9600 |
C23—H23A | 0.9700 | C12—H12B | 0.9600 |
C23—H23B | 0.9700 | C12—H12C | 0.9600 |
C19—H19A | 0.9700 | C21—H21A | 0.9700 |
C19—H19B | 0.9700 | C21—H21B | 0.9700 |
| | | |
C30—O12—C31 | 120.5 (4) | O10—C27—C29 | 111.1 (4) |
C25—O9—C27 | 110.6 (4) | O9—C27—C29 | 109.8 (5) |
C13—O6—C14 | 119.9 (4) | O10—C27—C28 | 108.9 (5) |
C20—O8—C22 | 106.9 (4) | O9—C27—C28 | 108.7 (4) |
C26—O10—C27 | 106.1 (4) | C29—C27—C28 | 113.0 (5) |
C10—O3—C8 | 109.8 (4) | O10—C26—C25 | 103.0 (4) |
C4—O1—C3 | 107.1 (5) | O10—C26—H26A | 111.2 |
C30—N2—C24 | 119.0 (4) | C25—C26—H26A | 111.2 |
C30—N2—C18 | 125.6 (4) | O10—C26—H26B | 111.2 |
C24—N2—C18 | 115.3 (4) | C25—C26—H26B | 111.2 |
C13—N1—C7 | 126.0 (4) | H26A—C26—H26B | 109.1 |
C13—N1—C1 | 118.3 (4) | O3—C10—O4 | 106.1 (4) |
C7—N1—C1 | 115.5 (4) | O3—C10—C11 | 110.7 (5) |
C5—O2—C3 | 109.2 (5) | O4—C10—C11 | 107.7 (6) |
C21—O7—C20 | 108.2 (5) | O3—C10—C12 | 106.6 (6) |
C9—O4—C10 | 108.6 (4) | O4—C10—C12 | 112.2 (5) |
O5—C13—N1 | 125.2 (5) | C11—C10—C12 | 113.3 (6) |
O5—C13—O6 | 124.3 (5) | C31—C32—H32A | 109.5 |
N1—C13—O6 | 110.4 (4) | C31—C32—H32B | 109.5 |
O11—C30—N2 | 125.4 (4) | H32A—C32—H32B | 109.5 |
O11—C30—O12 | 123.7 (5) | C31—C32—H32C | 109.5 |
N2—C30—O12 | 110.9 (4) | H32A—C32—H32C | 109.5 |
N2—C24—C25 | 111.2 (4) | H32B—C32—H32C | 109.5 |
N2—C24—C23 | 109.2 (4) | O6—C14—C15 | 110.9 (4) |
C25—C24—C23 | 113.0 (4) | O6—C14—C16 | 101.4 (4) |
N2—C24—H24 | 107.7 | C15—C14—C16 | 111.9 (5) |
C25—C24—H24 | 107.7 | O6—C14—C17 | 108.9 (4) |
C23—C24—H24 | 107.7 | C15—C14—C17 | 113.2 (5) |
N1—C7—C6 | 109.4 (4) | C16—C14—C17 | 109.8 (5) |
N1—C7—C8 | 110.7 (4) | C31—C33—H33A | 109.5 |
C6—C7—C8 | 113.2 (4) | C31—C33—H33B | 109.5 |
N1—C7—H7 | 107.8 | H33A—C33—H33B | 109.5 |
C6—C7—H7 | 107.8 | C31—C33—H33C | 109.5 |
C8—C7—H7 | 107.8 | H33A—C33—H33C | 109.5 |
O8—C20—O7 | 105.3 (4) | H33B—C33—H33C | 109.5 |
O8—C20—C23 | 109.9 (4) | C27—C28—H28A | 109.5 |
O7—C20—C23 | 109.6 (4) | C27—C28—H28B | 109.5 |
O8—C20—C19 | 110.9 (4) | H28A—C28—H28B | 109.5 |
O7—C20—C19 | 110.0 (4) | C27—C28—H28C | 109.5 |
C23—C20—C19 | 111.0 (4) | H28A—C28—H28C | 109.5 |
N2—C18—C19 | 109.8 (4) | H28B—C28—H28C | 109.5 |
N2—C18—H18A | 109.7 | C31—C34—H34A | 109.5 |
C19—C18—H18A | 109.7 | C31—C34—H34B | 109.5 |
N2—C18—H18B | 109.7 | H34A—C34—H34B | 109.5 |
C19—C18—H18B | 109.7 | C31—C34—H34C | 109.5 |
H18A—C18—H18B | 108.2 | H34A—C34—H34C | 109.5 |
N1—C1—C2 | 110.1 (4) | H34B—C34—H34C | 109.5 |
N1—C1—H1A | 109.6 | O8—C22—C21 | 103.4 (5) |
C2—C1—H1A | 109.6 | O8—C22—H22A | 111.1 |
N1—C1—H1B | 109.6 | C21—C22—H22A | 111.1 |
C2—C1—H1B | 109.6 | O8—C22—H22B | 111.1 |
H1A—C1—H1B | 108.1 | C21—C22—H22B | 111.1 |
C7—C6—C3 | 114.0 (4) | H22A—C22—H22B | 109.1 |
C7—C6—H6A | 108.7 | C14—C15—H15A | 109.5 |
C3—C6—H6A | 108.7 | C14—C15—H15B | 109.5 |
C7—C6—H6B | 108.7 | H15A—C15—H15B | 109.5 |
C3—C6—H6B | 108.7 | C14—C15—H15C | 109.5 |
H6A—C6—H6B | 107.6 | H15A—C15—H15C | 109.5 |
O2—C3—O1 | 106.4 (4) | H15B—C15—H15C | 109.5 |
O2—C3—C2 | 110.1 (4) | C27—C29—H29A | 109.5 |
O1—C3—C2 | 108.8 (4) | C27—C29—H29B | 109.5 |
O2—C3—C6 | 109.2 (4) | H29A—C29—H29B | 109.5 |
O1—C3—C6 | 109.6 (4) | C27—C29—H29C | 109.5 |
C2—C3—C6 | 112.5 (4) | H29A—C29—H29C | 109.5 |
O12—C31—C34 | 103.4 (4) | H29B—C29—H29C | 109.5 |
O12—C31—C32 | 110.8 (4) | C14—C16—H16A | 109.5 |
C34—C31—C32 | 110.7 (5) | C14—C16—H16B | 109.5 |
O12—C31—C33 | 110.0 (4) | H16A—C16—H16B | 109.5 |
C34—C31—C33 | 110.1 (5) | C14—C16—H16C | 109.5 |
C32—C31—C33 | 111.6 (5) | H16A—C16—H16C | 109.5 |
O9—C25—C24 | 111.4 (4) | H16B—C16—H16C | 109.5 |
O9—C25—C26 | 101.8 (4) | C10—C11—H11A | 109.5 |
C24—C25—C26 | 111.9 (4) | C10—C11—H11B | 109.5 |
O9—C25—H25 | 110.5 | H11A—C11—H11B | 109.5 |
C24—C25—H25 | 110.5 | C10—C11—H11C | 109.5 |
C26—C25—H25 | 110.5 | H11A—C11—H11C | 109.5 |
C20—C23—C24 | 115.0 (4) | H11B—C11—H11C | 109.5 |
C20—C23—H23A | 108.5 | C14—C17—H17A | 109.5 |
C24—C23—H23A | 108.5 | C14—C17—H17B | 109.5 |
C20—C23—H23B | 108.5 | H17A—C17—H17B | 109.5 |
C24—C23—H23B | 108.5 | C14—C17—H17C | 109.5 |
H23A—C23—H23B | 107.5 | H17A—C17—H17C | 109.5 |
C20—C19—C18 | 111.3 (4) | H17B—C17—H17C | 109.5 |
C20—C19—H19A | 109.4 | O1—C4—C5 | 106.5 (6) |
C18—C19—H19A | 109.4 | O1—C4—H4A | 110.4 |
C20—C19—H19B | 109.4 | C5—C4—H4A | 110.4 |
C18—C19—H19B | 109.4 | O1—C4—H4B | 110.4 |
H19A—C19—H19B | 108.0 | C5—C4—H4B | 110.4 |
C3—C2—C1 | 112.0 (4) | H4A—C4—H4B | 108.6 |
C3—C2—H2A | 109.2 | O2—C5—C4 | 107.7 (6) |
C1—C2—H2A | 109.2 | O2—C5—H5A | 110.2 |
C3—C2—H2B | 109.2 | C4—C5—H5A | 110.2 |
C1—C2—H2B | 109.2 | O2—C5—H5B | 110.2 |
H2A—C2—H2B | 107.9 | C4—C5—H5B | 110.2 |
O3—C8—C9 | 102.6 (4) | H5A—C5—H5B | 108.5 |
O3—C8—C7 | 108.0 (4) | C10—C12—H12A | 109.5 |
C9—C8—C7 | 114.3 (4) | C10—C12—H12B | 109.5 |
O3—C8—H8 | 110.5 | H12A—C12—H12B | 109.5 |
C9—C8—H8 | 110.5 | C10—C12—H12C | 109.5 |
C7—C8—H8 | 110.5 | H12A—C12—H12C | 109.5 |
O4—C9—C8 | 103.3 (4) | H12B—C12—H12C | 109.5 |
O4—C9—H9A | 111.1 | O7—C21—C22 | 107.0 (5) |
C8—C9—H9A | 111.1 | O7—C21—H21A | 110.3 |
O4—C9—H9B | 111.1 | C22—C21—H21A | 110.3 |
C8—C9—H9B | 111.1 | O7—C21—H21B | 110.3 |
H9A—C9—H9B | 109.1 | C22—C21—H21B | 110.3 |
O10—C27—O9 | 105.0 (4) | H21A—C21—H21B | 108.6 |
| | | |
C7—N1—C13—O5 | −174.9 (5) | N2—C24—C25—C26 | −158.5 (4) |
C1—N1—C13—O5 | 0.9 (7) | C23—C24—C25—C26 | 78.2 (5) |
C7—N1—C13—O6 | 7.0 (6) | O8—C20—C23—C24 | −73.4 (5) |
C1—N1—C13—O6 | −177.3 (4) | O7—C20—C23—C24 | 171.3 (4) |
C14—O6—C13—O5 | 9.6 (7) | C19—C20—C23—C24 | 49.6 (6) |
C14—O6—C13—N1 | −172.3 (4) | N2—C24—C23—C20 | −49.8 (6) |
C24—N2—C30—O11 | 7.3 (7) | C25—C24—C23—C20 | 74.5 (5) |
C18—N2—C30—O11 | −175.5 (5) | O8—C20—C19—C18 | 70.9 (6) |
C24—N2—C30—O12 | −173.4 (4) | O7—C20—C19—C18 | −173.0 (4) |
C18—N2—C30—O12 | 3.8 (7) | C23—C20—C19—C18 | −51.5 (6) |
C31—O12—C30—O11 | −5.8 (7) | N2—C18—C19—C20 | 55.2 (6) |
C31—O12—C30—N2 | 174.9 (4) | O2—C3—C2—C1 | −172.1 (4) |
C30—N2—C24—C25 | 106.8 (5) | O1—C3—C2—C1 | 71.7 (5) |
C18—N2—C24—C25 | −70.7 (5) | C6—C3—C2—C1 | −49.9 (6) |
C30—N2—C24—C23 | −127.8 (5) | N1—C1—C2—C3 | 54.4 (5) |
C18—N2—C24—C23 | 54.7 (5) | C10—O3—C8—C9 | −24.2 (6) |
C13—N1—C7—C6 | −129.2 (5) | C10—O3—C8—C7 | −145.2 (4) |
C1—N1—C7—C6 | 54.9 (5) | N1—C7—C8—O3 | −59.5 (5) |
C13—N1—C7—C8 | 105.4 (5) | C6—C7—C8—O3 | 177.3 (4) |
C1—N1—C7—C8 | −70.5 (5) | N1—C7—C8—C9 | −173.0 (4) |
C22—O8—C20—O7 | −31.4 (5) | C6—C7—C8—C9 | 63.8 (6) |
C22—O8—C20—C23 | −149.3 (4) | C10—O4—C9—C8 | −26.8 (6) |
C22—O8—C20—C19 | 87.6 (5) | O3—C8—C9—O4 | 30.6 (5) |
C21—O7—C20—O8 | 25.2 (6) | C7—C8—C9—O4 | 147.2 (4) |
C21—O7—C20—C23 | 143.3 (6) | C26—O10—C27—O9 | −29.8 (5) |
C21—O7—C20—C19 | −94.4 (6) | C26—O10—C27—C29 | 88.8 (5) |
C30—N2—C18—C19 | 123.8 (5) | C26—O10—C27—C28 | −146.1 (4) |
C24—N2—C18—C19 | −58.9 (6) | C25—O9—C27—O10 | 9.2 (5) |
C13—N1—C1—C2 | 124.9 (5) | C25—O9—C27—C29 | −110.3 (5) |
C7—N1—C1—C2 | −58.9 (5) | C25—O9—C27—C28 | 125.7 (5) |
N1—C7—C6—C3 | −48.0 (5) | C27—O10—C26—C25 | 37.5 (5) |
C8—C7—C6—C3 | 76.0 (5) | O9—C25—C26—O10 | −30.4 (5) |
C5—O2—C3—O1 | −10.4 (6) | C24—C25—C26—O10 | 88.6 (5) |
C5—O2—C3—C2 | −128.1 (6) | C8—O3—C10—O4 | 8.4 (6) |
C5—O2—C3—C6 | 107.8 (6) | C8—O3—C10—C11 | −108.3 (6) |
C4—O1—C3—O2 | 17.0 (6) | C8—O3—C10—C12 | 128.1 (5) |
C4—O1—C3—C2 | 135.6 (5) | C9—O4—C10—O3 | 12.5 (6) |
C4—O1—C3—C6 | −101.0 (5) | C9—O4—C10—C11 | 131.2 (5) |
C7—C6—C3—O2 | 170.0 (4) | C9—O4—C10—C12 | −103.5 (6) |
C7—C6—C3—O1 | −73.8 (5) | C13—O6—C14—C15 | −65.2 (6) |
C7—C6—C3—C2 | 47.4 (5) | C13—O6—C14—C16 | 175.9 (4) |
C30—O12—C31—C34 | −175.4 (4) | C13—O6—C14—C17 | 60.1 (6) |
C30—O12—C31—C32 | 66.0 (6) | C20—O8—C22—C21 | 24.9 (6) |
C30—O12—C31—C33 | −57.8 (6) | C3—O1—C4—C5 | −16.9 (8) |
C27—O9—C25—C24 | −106.4 (4) | C3—O2—C5—C4 | 0.0 (8) |
C27—O9—C25—C26 | 12.9 (5) | O1—C4—C5—O2 | 10.6 (9) |
N2—C24—C25—O9 | −45.4 (5) | C20—O7—C21—C22 | −9.5 (8) |
C23—C24—C25—O9 | −168.7 (4) | O8—C22—C21—O7 | −9.4 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O9i | 0.97 | 2.45 | 3.409 (6) | 171 |
C5—H5A···O5ii | 0.97 | 2.59 | 3.383 (10) | 139 |
C18—H18B···O2iii | 0.97 | 2.72 | 3.643 (7) | 158 |
C22—H22A···O11ii | 0.97 | 2.59 | 3.266 (7) | 127 |
C26—H26A···O3 | 0.97 | 2.70 | 3.558 (7) | 148 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z. |