The title compound, C
10H
28N
42+·2C
12H
27O
3SSi
−·2C
3H
8O, has been obtained by the reaction of (
tBuO)
3SiSH with spermine in the presence of 2-propanol. The sperminium cation sits on an inversion centre at the mid-point of the central C—C bond. The three species are linked together in infinite chains, mainly by N—H
S hydrogen bonds.
Supporting information
CCDC reference: 227919
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.131
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.88
Alert level B
REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?)
From the CIF: _diffrn_reflns_theta_max 24.99
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 4254
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4849
Completeness (_total/calc) 87.73%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.88
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C20
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT213_ALERT_2_C Atom C21A has ADP max/min Ratio ............. 3.10 prolat
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C30
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C2
PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
1 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 Software (Kuma Diffraction, 1996); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: RESVIEW (Schwenk, 1998); software used to prepare material for publication: SHELXL97.
Sperminium tri-
tert-butoxysilanethiolate–2-propanol (1/2)
top
Crystal data top
0.5C10H28N42+·C12H27O3SSi−·C3H8O | Z = 2 |
Mr = 441.76 | F(000) = 490 |
Triclinic, P1 | Dx = 1.064 Mg m−3 |
Hall symbol: -P 1 | Melting point = 357–358 K |
a = 9.419 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.970 (3) Å | Cell parameters from 65 reflections |
c = 13.525 (3) Å | θ = 5.9–31.9° |
α = 102.08 (3)° | µ = 0.19 mm−1 |
β = 108.64 (3)° | T = 200 K |
γ = 109.65 (3)° | Block, colourless |
V = 1378.4 (8) Å3 | 0.40 × 0.30 × 0.20 mm |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.020 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.7° |
Graphite monochromator | h = −10→10 |
ω/2θ scans | k = 0→14 |
4475 measured reflections | l = −15→15 |
4254 independent reflections | 3 standard reflections every 200 reflections |
2954 reflections with I > 2σ(I) | intensity decay: 0.8% |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0913P)2] where P = (Fo2 + 2Fc2)/3 |
4254 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 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 | Occ. (<1) |
S1 | 0.21329 (8) | −0.00162 (5) | 0.67539 (5) | 0.03494 (18) | |
Si1 | 0.26241 (7) | 0.16469 (5) | 0.76819 (5) | 0.02835 (18) | |
O1 | 0.18356 (19) | 0.17199 (14) | 0.85918 (13) | 0.0362 (4) | |
O2 | 0.1698 (2) | 0.21534 (13) | 0.67887 (13) | 0.0349 (4) | |
O3 | 0.45939 (19) | 0.25478 (14) | 0.83847 (14) | 0.0382 (4) | |
C10 | 0.2407 (3) | 0.1747 (2) | 0.9725 (2) | 0.0387 (6) | |
C11 | 0.0925 (4) | 0.1560 (3) | 1.0005 (3) | 0.0612 (8) | |
H11A | 0.0548 | 0.2163 | 0.9897 | 0.092* | |
H11B | 0.1249 | 0.1611 | 1.0785 | 0.092* | |
H11C | 0.0019 | 0.0784 | 0.9516 | 0.092* | |
C12 | 0.2959 (4) | 0.0791 (3) | 0.9815 (2) | 0.0602 (8) | |
H12A | 0.2039 | 0.0030 | 0.9301 | 0.090* | |
H12B | 0.3290 | 0.0796 | 1.0581 | 0.090* | |
H12C | 0.3907 | 0.0926 | 0.9621 | 0.090* | |
C13 | 0.3806 (4) | 0.2945 (3) | 1.0501 (2) | 0.0590 (8) | |
H13A | 0.4774 | 0.3072 | 1.0331 | 0.088* | |
H13B | 0.4111 | 0.2985 | 1.1277 | 0.088* | |
H13C | 0.3434 | 0.3551 | 1.0396 | 0.088* | |
C20 | 0.1548 (3) | 0.3243 (2) | 0.6926 (2) | 0.0370 (6) | |
C21 | 0.0173 (9) | 0.3149 (5) | 0.7231 (9) | 0.081 (3) | 0.628 (9) |
H21A | 0.0355 | 0.2942 | 0.7903 | 0.121* | 0.628 (9) |
H21B | −0.0871 | 0.2542 | 0.6618 | 0.121* | 0.628 (9) |
H21C | 0.0110 | 0.3902 | 0.7379 | 0.121* | 0.628 (9) |
C22 | 0.1195 (10) | 0.3393 (5) | 0.5786 (5) | 0.074 (3) | 0.628 (9) |
H22A | 0.1143 | 0.4143 | 0.5838 | 0.112* | 0.628 (9) |
H22B | 0.0131 | 0.2753 | 0.5225 | 0.112* | 0.628 (9) |
H22C | 0.2088 | 0.3378 | 0.5568 | 0.112* | 0.628 (9) |
C23 | 0.3189 (7) | 0.4288 (4) | 0.7784 (6) | 0.066 (2) | 0.628 (9) |
H23A | 0.3421 | 0.4237 | 0.8527 | 0.099* | 0.628 (9) |
H23B | 0.3097 | 0.5019 | 0.7787 | 0.099* | 0.628 (9) |
H23C | 0.4097 | 0.4275 | 0.7583 | 0.099* | 0.628 (9) |
C21A | 0.146 (2) | 0.3733 (12) | 0.8010 (10) | 0.091 (6) | 0.372 (9) |
H21D | 0.2484 | 0.3899 | 0.8639 | 0.137* | 0.372 (9) |
H21E | 0.0503 | 0.3159 | 0.8048 | 0.137* | 0.372 (9) |
H21F | 0.1330 | 0.4457 | 0.8046 | 0.137* | 0.372 (9) |
C22A | −0.0129 (15) | 0.2965 (8) | 0.5975 (9) | 0.072 (4) | 0.372 (9) |
H22D | −0.1050 | 0.2446 | 0.6085 | 0.109* | 0.372 (9) |
H22E | −0.0168 | 0.2580 | 0.5255 | 0.109* | 0.372 (9) |
H22F | −0.0228 | 0.3695 | 0.5984 | 0.109* | 0.372 (9) |
C23A | 0.2907 (14) | 0.4019 (9) | 0.6772 (16) | 0.089 (6) | 0.372 (9) |
H23D | 0.2735 | 0.3725 | 0.5994 | 0.134* | 0.372 (9) |
H23E | 0.3957 | 0.4053 | 0.7265 | 0.134* | 0.372 (9) |
H23F | 0.2952 | 0.4805 | 0.6952 | 0.134* | 0.372 (9) |
C30 | 0.6101 (3) | 0.2684 (2) | 0.8273 (2) | 0.0432 (6) | |
C31 | 0.7362 (3) | 0.3943 (3) | 0.9005 (3) | 0.0676 (9) | |
H31A | 0.6982 | 0.4482 | 0.8719 | 0.101* | |
H31B | 0.8443 | 0.4073 | 0.8995 | 0.101* | |
H31C | 0.7471 | 0.4082 | 0.9772 | 0.101* | |
C32 | 0.5841 (4) | 0.2455 (3) | 0.7077 (3) | 0.0663 (9) | |
H32A | 0.5076 | 0.1630 | 0.6631 | 0.100* | |
H32B | 0.6910 | 0.2630 | 0.7033 | 0.100* | |
H32C | 0.5367 | 0.2954 | 0.6788 | 0.100* | |
C33 | 0.6677 (4) | 0.1848 (3) | 0.8710 (3) | 0.0695 (10) | |
H33A | 0.6853 | 0.2019 | 0.9492 | 0.104* | |
H33B | 0.7723 | 0.1941 | 0.8656 | 0.104* | |
H33C | 0.5829 | 0.1042 | 0.8267 | 0.104* | |
N1 | 0.1851 (3) | 0.0889 (2) | 0.4654 (2) | 0.0400 (5) | |
H1A | 0.083 (4) | 0.078 (3) | 0.431 (3) | 0.060* | |
H1B | 0.256 (4) | 0.165 (3) | 0.478 (2) | 0.060* | |
H1C | 0.193 (4) | 0.071 (3) | 0.533 (3) | 0.060* | |
C40 | 0.2255 (3) | 0.0128 (2) | 0.3921 (2) | 0.0476 (7) | |
H40A | 0.1344 | −0.0675 | 0.3579 | 0.057* | |
H40B | 0.3285 | 0.0094 | 0.4376 | 0.057* | |
C41 | 0.2494 (4) | 0.0562 (2) | 0.3021 (2) | 0.0497 (7) | |
H41A | 0.1526 | 0.0703 | 0.2640 | 0.060* | |
H41B | 0.2511 | −0.0059 | 0.2463 | 0.060* | |
C42 | 0.4059 (4) | 0.1669 (3) | 0.3419 (3) | 0.0533 (7) | |
H42A | 0.5033 | 0.1549 | 0.3829 | 0.064* | |
H42B | 0.4183 | 0.1848 | 0.2766 | 0.064* | |
N2 | 0.4027 (3) | 0.26657 (19) | 0.41528 (19) | 0.0428 (5) | |
H2A | 0.323 (4) | 0.280 (3) | 0.375 (2) | 0.051* | |
C43 | 0.5589 (4) | 0.3725 (2) | 0.4566 (3) | 0.0551 (8) | |
H43A | 0.5766 | 0.3884 | 0.3920 | 0.066* | |
H43B | 0.6523 | 0.3578 | 0.4997 | 0.066* | |
C44 | 0.5621 (3) | 0.4795 (2) | 0.5295 (3) | 0.0521 (8) | |
H44A | 0.6752 | 0.5442 | 0.5612 | 0.062* | |
H44B | 0.5402 | 0.4622 | 0.5925 | 0.062* | |
C1 | 1.0323 (4) | 0.3760 (3) | 0.2083 (3) | 0.0666 (9) | |
H1D | 1.1168 | 0.3622 | 0.1876 | 0.100* | |
H1E | 1.0871 | 0.4399 | 0.2806 | 0.100* | |
H1F | 0.9655 | 0.3973 | 0.1514 | 0.100* | |
C2 | 0.9218 (4) | 0.2671 (3) | 0.2162 (3) | 0.0554 (8) | |
H2 | 0.8559 | 0.2062 | 0.1396 | 0.083* | |
C3 | 0.8038 (5) | 0.2854 (4) | 0.2603 (5) | 0.1141 (19) | |
H3A | 0.8660 | 0.3435 | 0.3362 | 0.171* | |
H3B | 0.7319 | 0.2112 | 0.2616 | 0.171* | |
H3C | 0.7353 | 0.3135 | 0.2123 | 0.171* | |
O4 | 1.0236 (2) | 0.22653 (18) | 0.28346 (18) | 0.0536 (5) | |
H4A | 0.958 (4) | 0.163 (3) | 0.283 (3) | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0404 (4) | 0.0269 (3) | 0.0361 (4) | 0.0148 (3) | 0.0148 (3) | 0.0106 (2) |
Si1 | 0.0287 (4) | 0.0253 (3) | 0.0295 (4) | 0.0105 (3) | 0.0122 (3) | 0.0093 (2) |
O1 | 0.0338 (9) | 0.0428 (9) | 0.0304 (9) | 0.0140 (7) | 0.0151 (7) | 0.0120 (7) |
O2 | 0.0445 (10) | 0.0283 (8) | 0.0337 (9) | 0.0198 (7) | 0.0142 (7) | 0.0112 (7) |
O3 | 0.0280 (9) | 0.0351 (9) | 0.0434 (10) | 0.0083 (7) | 0.0156 (7) | 0.0071 (7) |
C10 | 0.0390 (14) | 0.0440 (14) | 0.0284 (13) | 0.0139 (11) | 0.0142 (10) | 0.0113 (11) |
C11 | 0.0584 (19) | 0.084 (2) | 0.0437 (18) | 0.0251 (17) | 0.0306 (14) | 0.0222 (16) |
C12 | 0.087 (2) | 0.066 (2) | 0.0431 (17) | 0.0442 (18) | 0.0292 (16) | 0.0284 (15) |
C13 | 0.0581 (19) | 0.0536 (17) | 0.0386 (16) | 0.0086 (14) | 0.0129 (14) | 0.0047 (13) |
C20 | 0.0416 (14) | 0.0265 (12) | 0.0473 (16) | 0.0179 (10) | 0.0190 (12) | 0.0156 (10) |
C21 | 0.077 (5) | 0.043 (3) | 0.164 (10) | 0.039 (3) | 0.081 (6) | 0.045 (4) |
C22 | 0.114 (7) | 0.058 (3) | 0.070 (4) | 0.055 (4) | 0.034 (4) | 0.035 (3) |
C23 | 0.058 (3) | 0.032 (3) | 0.082 (5) | 0.013 (2) | 0.009 (3) | 0.012 (3) |
C21A | 0.194 (18) | 0.082 (9) | 0.075 (8) | 0.110 (12) | 0.085 (10) | 0.045 (7) |
C22A | 0.088 (8) | 0.052 (5) | 0.070 (7) | 0.047 (5) | 0.006 (6) | 0.024 (4) |
C23A | 0.075 (8) | 0.050 (6) | 0.189 (19) | 0.036 (6) | 0.081 (11) | 0.074 (9) |
C30 | 0.0264 (13) | 0.0514 (16) | 0.0463 (16) | 0.0150 (11) | 0.0130 (11) | 0.0142 (12) |
C31 | 0.0322 (16) | 0.060 (2) | 0.083 (2) | 0.0030 (14) | 0.0192 (15) | 0.0102 (17) |
C32 | 0.0410 (17) | 0.095 (3) | 0.057 (2) | 0.0191 (16) | 0.0279 (15) | 0.0227 (17) |
C33 | 0.0512 (19) | 0.073 (2) | 0.075 (2) | 0.0353 (17) | 0.0087 (16) | 0.0225 (18) |
N1 | 0.0340 (12) | 0.0419 (12) | 0.0361 (13) | 0.0077 (10) | 0.0151 (10) | 0.0136 (10) |
C40 | 0.0421 (15) | 0.0334 (14) | 0.0576 (18) | 0.0128 (11) | 0.0167 (13) | 0.0111 (12) |
C41 | 0.0521 (17) | 0.0476 (16) | 0.0419 (16) | 0.0208 (13) | 0.0205 (13) | 0.0027 (12) |
C42 | 0.0543 (18) | 0.0605 (18) | 0.0535 (18) | 0.0221 (14) | 0.0349 (14) | 0.0214 (14) |
N2 | 0.0396 (13) | 0.0402 (12) | 0.0486 (14) | 0.0134 (10) | 0.0207 (10) | 0.0190 (10) |
C43 | 0.0441 (16) | 0.0475 (16) | 0.071 (2) | 0.0097 (13) | 0.0269 (14) | 0.0284 (14) |
C44 | 0.0408 (16) | 0.0424 (16) | 0.0580 (19) | 0.0054 (12) | 0.0139 (13) | 0.0221 (13) |
C1 | 0.087 (2) | 0.0499 (18) | 0.070 (2) | 0.0329 (17) | 0.0313 (19) | 0.0320 (16) |
C2 | 0.0555 (18) | 0.0463 (16) | 0.0620 (19) | 0.0256 (14) | 0.0134 (14) | 0.0273 (14) |
C3 | 0.094 (3) | 0.129 (4) | 0.212 (6) | 0.087 (3) | 0.096 (4) | 0.119 (4) |
O4 | 0.0481 (12) | 0.0513 (12) | 0.0731 (14) | 0.0264 (10) | 0.0245 (10) | 0.0376 (11) |
Geometric parameters (Å, º) top
S1—Si1 | 2.0657 (12) | C30—C33 | 1.510 (4) |
Si1—O1 | 1.6302 (18) | C30—C31 | 1.524 (4) |
Si1—O3 | 1.6312 (19) | C31—H31A | 0.9800 |
Si1—O2 | 1.6418 (17) | C31—H31B | 0.9800 |
O1—C10 | 1.441 (3) | C31—H31C | 0.9800 |
O2—C20 | 1.446 (3) | C32—H32A | 0.9800 |
O3—C30 | 1.431 (3) | C32—H32B | 0.9800 |
C10—C12 | 1.510 (4) | C32—H32C | 0.9800 |
C10—C11 | 1.517 (4) | C33—H33A | 0.9800 |
C10—C13 | 1.520 (4) | C33—H33B | 0.9800 |
C11—H11A | 0.9800 | C33—H33C | 0.9800 |
C11—H11B | 0.9800 | N1—C40 | 1.479 (3) |
C11—H11C | 0.9800 | N1—H1A | 0.87 (3) |
C12—H12A | 0.9800 | N1—H1B | 0.93 (3) |
C12—H12B | 0.9800 | N1—H1C | 0.98 (3) |
C12—H12C | 0.9800 | C40—C41 | 1.492 (4) |
C13—H13A | 0.9800 | C40—H40A | 0.9900 |
C13—H13B | 0.9800 | C40—H40B | 0.9900 |
C13—H13C | 0.9800 | C41—C42 | 1.507 (4) |
C20—C23A | 1.445 (9) | C41—H41A | 0.9900 |
C20—C21 | 1.456 (6) | C41—H41B | 0.9900 |
C20—C21A | 1.512 (9) | C42—N2 | 1.472 (4) |
C20—C23 | 1.537 (5) | C42—H42A | 0.9900 |
C20—C22 | 1.539 (6) | C42—H42B | 0.9900 |
C20—C22A | 1.550 (9) | N2—C43 | 1.469 (3) |
C21—H21A | 0.9800 | N2—H2A | 0.87 (3) |
C21—H21B | 0.9800 | C43—C44 | 1.510 (4) |
C21—H21C | 0.9800 | C43—H43A | 0.9900 |
C22—H22A | 0.9800 | C43—H43B | 0.9900 |
C22—H22B | 0.9800 | C44—C44i | 1.512 (6) |
C22—H22C | 0.9800 | C44—H44A | 0.9900 |
C23—H23A | 0.9800 | C44—H44B | 0.9900 |
C23—H23B | 0.9800 | C1—C2 | 1.496 (4) |
C23—H23C | 0.9800 | C1—H1D | 0.9800 |
C21A—H21D | 0.9800 | C1—H1E | 0.9800 |
C21A—H21E | 0.9800 | C1—H1F | 0.9800 |
C21A—H21F | 0.9800 | C2—O4 | 1.416 (3) |
C22A—H22D | 0.9800 | C2—C3 | 1.479 (5) |
C22A—H22E | 0.9800 | C2—H2 | 1.0000 |
C22A—H22F | 0.9800 | C3—H3A | 0.9800 |
C23A—H23D | 0.9800 | C3—H3B | 0.9800 |
C23A—H23E | 0.9800 | C3—H3C | 0.9800 |
C23A—H23F | 0.9800 | O4—H4A | 0.84 (3) |
C30—C32 | 1.503 (4) | | |
| | | |
O1—Si1—O3 | 105.01 (9) | O3—C30—C31 | 105.9 (2) |
O1—Si1—O2 | 104.59 (9) | C32—C30—C31 | 111.0 (3) |
O3—Si1—O2 | 110.09 (9) | C33—C30—C31 | 109.7 (2) |
O1—Si1—S1 | 115.78 (7) | C30—C31—H31A | 109.5 |
O3—Si1—S1 | 114.98 (8) | C30—C31—H31B | 109.5 |
O2—Si1—S1 | 105.90 (7) | H31A—C31—H31B | 109.5 |
C10—O1—Si1 | 132.71 (15) | C30—C31—H31C | 109.5 |
C20—O2—Si1 | 132.42 (15) | H31A—C31—H31C | 109.5 |
C30—O3—Si1 | 136.31 (16) | H31B—C31—H31C | 109.5 |
O1—C10—C12 | 110.5 (2) | C30—C32—H32A | 109.5 |
O1—C10—C11 | 105.3 (2) | C30—C32—H32B | 109.5 |
C12—C10—C11 | 111.0 (3) | H32A—C32—H32B | 109.5 |
O1—C10—C13 | 109.8 (2) | C30—C32—H32C | 109.5 |
C12—C10—C13 | 111.2 (2) | H32A—C32—H32C | 109.5 |
C11—C10—C13 | 108.8 (2) | H32B—C32—H32C | 109.5 |
C10—C11—H11A | 109.5 | C30—C33—H33A | 109.5 |
C10—C11—H11B | 109.5 | C30—C33—H33B | 109.5 |
H11A—C11—H11B | 109.5 | H33A—C33—H33B | 109.5 |
C10—C11—H11C | 109.5 | C30—C33—H33C | 109.5 |
H11A—C11—H11C | 109.5 | H33A—C33—H33C | 109.5 |
H11B—C11—H11C | 109.5 | H33B—C33—H33C | 109.5 |
C10—C12—H12A | 109.5 | C40—N1—H1A | 110 (2) |
C10—C12—H12B | 109.5 | C40—N1—H1B | 105.1 (19) |
H12A—C12—H12B | 109.5 | H1A—N1—H1B | 109 (3) |
C10—C12—H12C | 109.5 | C40—N1—H1C | 112.2 (18) |
H12A—C12—H12C | 109.5 | H1A—N1—H1C | 106 (3) |
H12B—C12—H12C | 109.5 | H1B—N1—H1C | 115 (2) |
C10—C13—H13A | 109.5 | N1—C40—C41 | 112.0 (2) |
C10—C13—H13B | 109.5 | N1—C40—H40A | 109.2 |
H13A—C13—H13B | 109.5 | C41—C40—H40A | 109.2 |
C10—C13—H13C | 109.5 | N1—C40—H40B | 109.2 |
H13A—C13—H13C | 109.5 | C41—C40—H40B | 109.2 |
H13B—C13—H13C | 109.5 | H40A—C40—H40B | 107.9 |
C23A—C20—O2 | 106.1 (4) | C40—C41—C42 | 114.5 (2) |
C23A—C20—C21 | 145.0 (5) | C40—C41—H41A | 108.6 |
O2—C20—C21 | 108.7 (3) | C42—C41—H41A | 108.6 |
C23A—C20—C21A | 114.5 (9) | C40—C41—H41B | 108.6 |
O2—C20—C21A | 113.3 (4) | C42—C41—H41B | 108.6 |
O2—C20—C23 | 111.3 (3) | H41A—C41—H41B | 107.6 |
C21—C20—C23 | 112.2 (4) | N2—C42—C41 | 111.5 (2) |
C21A—C20—C23 | 67.8 (7) | N2—C42—H42A | 109.3 |
C23A—C20—C22 | 61.4 (7) | C41—C42—H42A | 109.3 |
O2—C20—C22 | 105.7 (3) | N2—C42—H42B | 109.3 |
C21—C20—C22 | 111.2 (5) | C41—C42—H42B | 109.3 |
C21A—C20—C22 | 139.7 (5) | H42A—C42—H42B | 108.0 |
C23—C20—C22 | 107.5 (4) | C43—N2—C42 | 110.6 (2) |
C23A—C20—C22A | 109.6 (8) | C43—N2—H2A | 108 (2) |
O2—C20—C22A | 106.6 (4) | C42—N2—H2A | 107 (2) |
C21A—C20—C22A | 106.6 (8) | N2—C43—C44 | 113.5 (2) |
C23—C20—C22A | 140.6 (4) | N2—C43—H43A | 108.9 |
C20—C21—H21A | 109.5 | C44—C43—H43A | 108.9 |
C20—C21—H21B | 109.5 | N2—C43—H43B | 108.9 |
C20—C21—H21C | 109.5 | C44—C43—H43B | 108.9 |
C20—C22—H22A | 109.5 | H43A—C43—H43B | 107.7 |
C20—C22—H22B | 109.5 | C43—C44—C44i | 114.7 (3) |
C20—C22—H22C | 109.5 | C43—C44—H44A | 108.6 |
C20—C23—H23A | 109.5 | C44i—C44—H44A | 108.6 |
C20—C23—H23B | 109.5 | C43—C44—H44B | 108.6 |
C20—C23—H23C | 109.5 | C44i—C44—H44B | 108.6 |
C20—C21A—H21D | 109.5 | H44A—C44—H44B | 107.6 |
C20—C21A—H21E | 109.5 | C2—C1—H1D | 109.5 |
H21D—C21A—H21E | 109.5 | C2—C1—H1E | 109.5 |
C20—C21A—H21F | 109.5 | H1D—C1—H1E | 109.5 |
H21D—C21A—H21F | 109.5 | C2—C1—H1F | 109.5 |
H21E—C21A—H21F | 109.5 | H1D—C1—H1F | 109.5 |
C20—C22A—H22D | 109.5 | H1E—C1—H1F | 109.5 |
C20—C22A—H22E | 109.5 | O4—C2—C3 | 111.3 (3) |
H22D—C22A—H22E | 109.5 | O4—C2—C1 | 108.3 (3) |
C20—C22A—H22F | 109.5 | C3—C2—C1 | 112.6 (3) |
H22D—C22A—H22F | 109.5 | O4—C2—H2 | 108.2 |
H22E—C22A—H22F | 109.5 | C3—C2—H2 | 108.2 |
C20—C23A—H23D | 109.5 | C1—C2—H2 | 108.2 |
C20—C23A—H23E | 109.5 | C2—C3—H3A | 109.5 |
H23D—C23A—H23E | 109.5 | C2—C3—H3B | 109.5 |
C20—C23A—H23F | 109.5 | H3A—C3—H3B | 109.5 |
H23D—C23A—H23F | 109.5 | C2—C3—H3C | 109.5 |
H23E—C23A—H23F | 109.5 | H3A—C3—H3C | 109.5 |
O3—C30—C32 | 111.1 (2) | H3B—C3—H3C | 109.5 |
O3—C30—C33 | 108.2 (2) | C2—O4—H4A | 106 (2) |
C32—C30—C33 | 110.8 (3) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1ii | 0.87 (3) | 2.41 (3) | 3.265 (3) | 167 (3) |
N1—H1B···N2 | 0.93 (3) | 2.09 (3) | 2.887 (3) | 144 (3) |
N1—H1C···S1 | 0.98 (3) | 2.30 (3) | 3.262 (3) | 169 (3) |
N2—H2A···O4iii | 0.87 (3) | 2.46 (3) | 3.239 (3) | 150 (3) |
O4—H4A···S1iv | 0.84 (3) | 2.48 (3) | 3.301 (2) | 167 (3) |
Symmetry codes: (ii) −x, −y, −z+1; (iii) x−1, y, z; (iv) −x+1, −y, −z+1. |