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In the title molecular structure, C12H18N4OS2+·2C6H2N3O7-, the thiazolium ring bearing the hydroxyethyl side chain is disordered over two sites about the methylene bridge. In the minor occupancy component, the dihedral angles are quite different from the range observed in related structures. In the crystal structure, the thiaminium cation and one of the picrate anions form a centrosymmetric hydrogen-bonded cluster. Both anions form `anionic holes' with the thiaminium cation.
Supporting information
CCDC reference: 610831
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.067
- wR factor = 0.240
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C141
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C142
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for S111
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C7
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C131
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C101
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N13
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT430_ALERT_2_B Short Inter D...A Contact O14 .. O161 .. 2.83 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O15 .. N82 .. 2.86 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT213_ALERT_2_C Atom O151 has ADP max/min Ratio ............. 3.20 prolat
PLAT213_ALERT_2_C Atom O152 has ADP max/min Ratio ............. 3.20 prolat
PLAT213_ALERT_2_C Atom C192 has ADP max/min Ratio ............. 3.80 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.50 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.28 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S112
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C132
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C91
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N82
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C92
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N11
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N12
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N21
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N22
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N23
| Author Response: As the end terminal oxygen, it has large high Ueq
value. As well it is in disordered state. So, the comparision of this Carbon
with that atom can be overlooked.
|
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.00
PLAT301_ALERT_3_C Main Residue Disorder ......................... 18.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT414_ALERT_2_C Short Intra D-H..H-X H4B .. H7B .. 1.91 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O21 .. C6 .. 2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact O24 .. C13 .. 2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O21 .. 2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A .. O12 .. 2.65 Ang.
2 ALERT level A = In general: serious problem
8 ALERT level B = Potentially serious problem
28 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
28 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.
Crystal data top
C12H18N4OS2+·2C6H2N3O7− | Z = 2 |
Mr = 722.58 | F(000) = 744 |
Triclinic, P1 | Dx = 1.594 Mg m−3 Dm = 1.59 Mg m−3 Dm measured by flotation using a liquid mixture of bromoform and xylene |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.269 (3) Å | Cell parameters from 25 reflections |
b = 12.252 (4) Å | θ = 10.4–14.8° |
c = 16.641 (3) Å | µ = 0.20 mm−1 |
α = 69.35 (4)° | T = 293 K |
β = 86.35 (5)° | Needle, yellow |
γ = 72.82 (3)° | 0.20 × 0.17 × 0.15 mm |
V = 1505.6 (9) Å3 | |
Data collection top
Nonius MACH3 sealed-tube diffractometer | 2399 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.02 |
Graphite monochromator | θmax = 25°, θmin = 2.6° |
ω–2θ scans | h = −1→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.946, Tmax = 0.960 | l = −19→19 |
6473 measured reflections | 3 standard reflections every 60 min |
5276 independent reflections | 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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1133P)2 + 0.9209P] where P = (Fo2 + 2Fc2)/3 |
5276 reflections | (Δ/σ)max = 0.003 |
518 parameters | Δρmax = 0.54 e Å−3 |
5 restraints | Δρmin = −0.29 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) |
C11 | 0.4718 (6) | 0.2789 (4) | 0.9949 (3) | 0.0506 (11) | |
C12 | 0.6050 (6) | 0.3123 (4) | 0.9421 (3) | 0.0535 (11) | |
C13 | 0.5930 (7) | 0.4295 (5) | 0.8901 (3) | 0.0617 (13) | |
H13 | 0.6835 | 0.4461 | 0.8569 | 0.074* | |
C14 | 0.4491 (7) | 0.5228 (4) | 0.8862 (3) | 0.0631 (14) | |
C15 | 0.3172 (7) | 0.4999 (4) | 0.9368 (3) | 0.0598 (13) | |
H15 | 0.2213 | 0.5634 | 0.9362 | 0.072* | |
C16 | 0.3282 (6) | 0.3839 (4) | 0.9878 (3) | 0.0541 (12) | |
N11 | 0.7614 (6) | 0.2191 (5) | 0.9417 (3) | 0.0717 (12) | |
N12 | 0.4363 (10) | 0.6446 (5) | 0.8272 (4) | 0.0975 (18) | |
N13 | 0.1842 (6) | 0.3632 (5) | 1.0386 (4) | 0.0782 (13) | |
O11 | 0.4731 (4) | 0.1726 (3) | 1.0432 (2) | 0.0651 (9) | |
O12 | 0.7596 (6) | 0.1137 (4) | 0.9661 (3) | 0.1257 (19) | |
O13 | 0.8841 (5) | 0.2498 (5) | 0.9138 (3) | 0.1103 (16) | |
O14 | 0.5477 (9) | 0.6596 (5) | 0.7765 (4) | 0.154 (3) | |
O15 | 0.3122 (8) | 0.7277 (4) | 0.8310 (3) | 0.129 (2) | |
O16 | 0.1173 (10) | 0.4278 (9) | 1.0811 (7) | 0.111 (3) | 0.65 |
O161 | 0.198 (2) | 0.351 (2) | 1.1126 (12) | 0.134 (7) | 0.35 |
O17 | 0.1080 (8) | 0.3034 (7) | 1.0261 (4) | 0.163 (3) | |
C21 | 0.7765 (6) | 0.4738 (5) | 0.5052 (3) | 0.0691 (15) | |
C22 | 0.6985 (6) | 0.4239 (5) | 0.4565 (3) | 0.0685 (14) | |
C23 | 0.5852 (6) | 0.4936 (5) | 0.3889 (3) | 0.0707 (15) | |
H23 | 0.5379 | 0.4568 | 0.3602 | 0.085* | |
C24 | 0.5403 (6) | 0.6200 (5) | 0.3630 (3) | 0.0675 (15) | |
C25 | 0.6079 (6) | 0.6758 (5) | 0.4047 (3) | 0.0708 (15) | |
H25 | 0.5782 | 0.7604 | 0.3867 | 0.085* | |
C26 | 0.7200 (6) | 0.6052 (5) | 0.4733 (3) | 0.0687 (14) | |
N21 | 0.7391 (9) | 0.2910 (5) | 0.4802 (4) | 0.106 (2) | |
N22 | 0.4132 (6) | 0.6924 (6) | 0.2930 (3) | 0.0880 (16) | |
N23 | 0.7792 (7) | 0.6717 (6) | 0.5163 (4) | 0.0991 (16) | |
O21 | 0.8819 (5) | 0.4105 (4) | 0.5659 (2) | 0.0973 (14) | |
O22 | 0.8059 (8) | 0.2272 (5) | 0.5500 (4) | 0.153 (2) | |
O23 | 0.6506 (17) | 0.2455 (10) | 0.4424 (8) | 0.124 (4) | 0.55 |
O231 | 0.775 (2) | 0.2640 (14) | 0.4225 (13) | 0.148 (6) | 0.45 |
O24 | 0.3423 (6) | 0.6395 (5) | 0.2637 (3) | 0.1163 (18) | |
O25 | 0.3846 (7) | 0.8034 (5) | 0.2682 (3) | 0.134 (2) | |
O26 | 0.7734 (8) | 0.7784 (5) | 0.4744 (4) | 0.1342 (19) | |
O27 | 0.8380 (8) | 0.6208 (5) | 0.5891 (3) | 0.145 (2) | |
N1 | −0.0408 (5) | 0.6618 (3) | 0.2815 (2) | 0.0536 (10) | |
H1 | 0.0289 | 0.6052 | 0.3212 | 0.064* | |
C2 | −0.1235 (6) | 0.6316 (4) | 0.2297 (3) | 0.0493 (11) | |
C3 | −0.0845 (7) | 0.4997 (4) | 0.2418 (3) | 0.0717 (15) | |
H3B | −0.1878 | 0.4811 | 0.2376 | 0.108* | |
H3A | −0.0299 | 0.4511 | 0.2975 | 0.108* | |
H3C | −0.0106 | 0.4822 | 0.1982 | 0.108* | |
N3 | −0.2338 (5) | 0.7143 (3) | 0.1700 (2) | 0.0523 (9) | |
C4 | −0.2608 (6) | 0.8335 (4) | 0.1583 (3) | 0.0521 (11) | |
N4 | −0.3703 (5) | 0.9128 (3) | 0.0954 (3) | 0.0785 (14) | |
H4A | −0.4199 | 0.8876 | 0.0646 | 0.094* | |
H4B | −0.3920 | 0.9897 | 0.0853 | 0.094* | |
C5 | −0.1737 (6) | 0.8693 (4) | 0.2101 (3) | 0.0610 (13) | |
C6 | −0.0648 (6) | 0.7790 (4) | 0.2724 (3) | 0.0642 (14) | |
H6 | −0.0063 | 0.7981 | 0.3091 | 0.077* | |
C7 | −0.2106 (9) | 1.0025 (5) | 0.1960 (5) | 0.112 (3) | |
H7A | −0.2921 | 1.0240 | 0.2365 | 0.134* | 0.54 |
H7B | −0.2589 | 1.0510 | 0.1383 | 0.134* | 0.54 |
H7C | −0.1827 | 1.0448 | 0.1381 | 0.134* | 0.46 |
H7D | −0.3311 | 1.0360 | 0.2012 | 0.134* | 0.46 |
N81 | −0.042 (3) | 1.0303 (10) | 0.2087 (10) | 0.084 (6) | 0.54 |
C91 | −0.0251 (16) | 1.0448 (8) | 0.2891 (8) | 0.054 (2) | 0.54 |
C191 | −0.150 (3) | 1.0251 (19) | 0.3582 (11) | 0.083 (7)* | 0.54 |
H19A | −0.2427 | 1.0086 | 0.3377 | 0.125* | 0.54 |
H19B | −0.1913 | 1.0970 | 0.3732 | 0.125* | 0.54 |
H19C | −0.0952 | 0.9571 | 0.4079 | 0.125* | 0.54 |
C101 | 0.110 (2) | 1.0726 (17) | 0.2985 (12) | 0.053 (6)* | 0.54 |
S111 | 0.2275 (5) | 1.0886 (3) | 0.2078 (2) | 0.0975 (10) | 0.54 |
C121 | 0.073 (3) | 1.0549 (18) | 0.155 (2) | 0.078 (5) | 0.54 |
H12A | 0.0764 | 1.0552 | 0.0988 | 0.093* | 0.54 |
C131 | 0.1618 (13) | 1.1037 (13) | 0.3725 (9) | 0.110 (3) | 0.54 |
H13A | 0.1341 | 1.1917 | 0.3553 | 0.132* | 0.54 |
H13B | 0.0956 | 1.0758 | 0.4216 | 0.132* | 0.54 |
C141 | 0.3411 (14) | 1.0506 (11) | 0.3989 (9) | 0.099 (4) | 0.54 |
H14A | 0.3776 | 1.0959 | 0.4280 | 0.118* | 0.54 |
H14B | 0.3651 | 0.9660 | 0.4365 | 0.118* | 0.54 |
O151 | 0.418 (3) | 1.061 (4) | 0.3216 (12) | 0.54 (3) | 0.54 |
N82 | −0.1140 (18) | 1.0269 (9) | 0.2576 (10) | 0.060 (3) | 0.46 |
C92 | 0.031 (2) | 1.0444 (13) | 0.2327 (13) | 0.062 (4) | 0.46 |
C192 | 0.130 (4) | 1.036 (3) | 0.157 (2) | 0.109 (12) | 0.46 |
H19D | 0.0766 | 1.0035 | 0.1250 | 0.164* | 0.46 |
H19E | 0.2428 | 0.9827 | 0.1758 | 0.164* | 0.46 |
H19F | 0.1358 | 1.1154 | 0.1213 | 0.164* | 0.46 |
C102 | 0.111 (4) | 1.080 (3) | 0.2845 (18) | 0.082 (11)* | 0.46 |
S112 | −0.0236 (5) | 1.0763 (4) | 0.3756 (2) | 0.0937 (11) | 0.46 |
C122 | −0.166 (2) | 1.0405 (19) | 0.3300 (13) | 0.072 (5) | 0.46 |
H12B | −0.2685 | 1.0315 | 0.3533 | 0.087* | 0.46 |
C132 | 0.2670 (17) | 1.1170 (15) | 0.2873 (8) | 0.110 (3) | 0.46 |
H13C | 0.2176 | 1.2040 | 0.2742 | 0.132* | 0.46 |
H13D | 0.3174 | 1.1101 | 0.2344 | 0.132* | 0.46 |
C142 | 0.4283 (18) | 1.0933 (14) | 0.3419 (10) | 0.099 (4) | 0.46 |
H14C | 0.5309 | 1.0601 | 0.3162 | 0.118* | 0.46 |
H14D | 0.4337 | 1.1671 | 0.3495 | 0.118* | 0.46 |
O152 | 0.401 (5) | 1.007 (4) | 0.4204 (16) | 0.54 (3) | 0.46 |
H151 | 0.4587 | 1.1411 | 0.3194 | 0.050* | 0.54 |
H152 | 0.5373 | 0.9543 | 0.4237 | 0.050* | 0.46 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.056 (3) | 0.042 (3) | 0.052 (3) | −0.006 (2) | −0.012 (2) | −0.018 (2) |
C12 | 0.059 (3) | 0.048 (3) | 0.051 (3) | −0.007 (2) | −0.007 (2) | −0.019 (2) |
C13 | 0.073 (3) | 0.063 (3) | 0.054 (3) | −0.031 (3) | −0.005 (2) | −0.017 (2) |
C14 | 0.079 (4) | 0.041 (3) | 0.064 (3) | −0.016 (3) | −0.024 (3) | −0.010 (2) |
C15 | 0.069 (3) | 0.041 (3) | 0.066 (3) | −0.003 (2) | −0.021 (3) | −0.021 (2) |
C16 | 0.057 (3) | 0.051 (3) | 0.055 (3) | −0.009 (2) | −0.005 (2) | −0.023 (2) |
N11 | 0.069 (3) | 0.075 (3) | 0.058 (3) | −0.002 (3) | 0.002 (2) | −0.022 (2) |
N12 | 0.135 (5) | 0.055 (3) | 0.088 (4) | −0.036 (4) | −0.035 (4) | 0.005 (3) |
N13 | 0.068 (3) | 0.072 (3) | 0.090 (4) | −0.012 (3) | −0.001 (3) | −0.029 (3) |
O11 | 0.074 (2) | 0.0423 (18) | 0.067 (2) | −0.0082 (16) | −0.0055 (17) | −0.0107 (16) |
O12 | 0.120 (4) | 0.065 (3) | 0.150 (4) | 0.011 (3) | 0.050 (3) | −0.026 (3) |
O13 | 0.060 (3) | 0.132 (4) | 0.140 (4) | −0.026 (3) | 0.006 (3) | −0.049 (3) |
O14 | 0.179 (6) | 0.093 (4) | 0.152 (5) | −0.067 (4) | 0.000 (4) | 0.026 (3) |
O15 | 0.166 (5) | 0.042 (2) | 0.148 (5) | −0.005 (3) | −0.051 (4) | −0.007 (3) |
O16 | 0.074 (6) | 0.146 (8) | 0.115 (7) | 0.003 (5) | 0.015 (5) | −0.079 (6) |
O161 | 0.097 (13) | 0.20 (2) | 0.086 (12) | −0.009 (12) | 0.025 (10) | −0.053 (13) |
O17 | 0.132 (5) | 0.243 (8) | 0.179 (6) | −0.120 (5) | 0.064 (4) | −0.107 (6) |
C21 | 0.053 (3) | 0.080 (4) | 0.044 (3) | 0.004 (3) | 0.003 (2) | −0.005 (3) |
C22 | 0.059 (3) | 0.076 (4) | 0.053 (3) | 0.005 (3) | 0.005 (3) | −0.022 (3) |
C23 | 0.056 (3) | 0.092 (4) | 0.052 (3) | −0.002 (3) | 0.002 (2) | −0.028 (3) |
C24 | 0.049 (3) | 0.086 (4) | 0.039 (2) | 0.003 (3) | −0.003 (2) | −0.005 (3) |
C25 | 0.062 (3) | 0.071 (3) | 0.053 (3) | −0.003 (3) | 0.002 (3) | −0.005 (3) |
C26 | 0.057 (3) | 0.087 (4) | 0.052 (3) | −0.013 (3) | −0.006 (3) | −0.017 (3) |
N21 | 0.106 (5) | 0.083 (4) | 0.092 (4) | 0.018 (4) | 0.003 (4) | −0.024 (4) |
N22 | 0.063 (3) | 0.117 (5) | 0.050 (3) | 0.006 (3) | −0.007 (2) | −0.012 (3) |
N23 | 0.097 (4) | 0.102 (4) | 0.088 (4) | −0.027 (4) | −0.013 (3) | −0.020 (3) |
O21 | 0.085 (3) | 0.110 (3) | 0.055 (2) | 0.009 (2) | −0.026 (2) | −0.005 (2) |
O22 | 0.155 (5) | 0.086 (3) | 0.160 (5) | −0.009 (3) | −0.047 (4) | 0.012 (4) |
O23 | 0.163 (11) | 0.100 (7) | 0.124 (8) | −0.031 (8) | −0.018 (8) | −0.058 (6) |
O231 | 0.163 (15) | 0.104 (10) | 0.193 (16) | −0.029 (10) | 0.053 (12) | −0.086 (10) |
O24 | 0.091 (3) | 0.174 (5) | 0.070 (3) | −0.008 (3) | −0.025 (2) | −0.047 (3) |
O25 | 0.123 (4) | 0.112 (4) | 0.097 (3) | 0.010 (3) | −0.041 (3) | 0.016 (3) |
O26 | 0.160 (5) | 0.109 (4) | 0.137 (4) | −0.045 (4) | −0.017 (4) | −0.038 (4) |
O27 | 0.200 (6) | 0.152 (5) | 0.084 (3) | −0.058 (4) | −0.054 (4) | −0.024 (3) |
N1 | 0.051 (2) | 0.046 (2) | 0.050 (2) | 0.0017 (17) | −0.0120 (18) | −0.0118 (17) |
C2 | 0.053 (3) | 0.045 (2) | 0.040 (2) | −0.006 (2) | −0.005 (2) | −0.0092 (19) |
C3 | 0.100 (4) | 0.044 (3) | 0.062 (3) | −0.012 (3) | −0.011 (3) | −0.013 (2) |
N3 | 0.060 (2) | 0.044 (2) | 0.044 (2) | −0.0075 (18) | −0.0117 (18) | −0.0091 (16) |
C4 | 0.057 (3) | 0.045 (3) | 0.046 (2) | −0.007 (2) | −0.012 (2) | −0.010 (2) |
N4 | 0.102 (3) | 0.044 (2) | 0.080 (3) | −0.013 (2) | −0.053 (3) | −0.007 (2) |
C5 | 0.072 (3) | 0.043 (3) | 0.061 (3) | −0.005 (2) | −0.024 (3) | −0.015 (2) |
C6 | 0.068 (3) | 0.053 (3) | 0.068 (3) | −0.001 (2) | −0.030 (3) | −0.024 (2) |
C7 | 0.123 (5) | 0.056 (3) | 0.150 (6) | 0.005 (3) | −0.096 (5) | −0.037 (4) |
N81 | 0.140 (15) | 0.039 (5) | 0.059 (10) | 0.006 (7) | −0.051 (12) | −0.018 (6) |
C91 | 0.055 (7) | 0.046 (5) | 0.063 (7) | −0.010 (4) | −0.012 (7) | −0.022 (5) |
S111 | 0.100 (2) | 0.094 (2) | 0.088 (2) | −0.0327 (19) | 0.0315 (19) | −0.0207 (17) |
C121 | 0.079 (16) | 0.059 (9) | 0.059 (10) | 0.013 (11) | −0.007 (12) | −0.004 (8) |
C131 | 0.095 (7) | 0.154 (9) | 0.105 (7) | −0.047 (7) | −0.007 (6) | −0.062 (7) |
C141 | 0.102 (9) | 0.069 (6) | 0.124 (10) | −0.036 (5) | −0.047 (7) | −0.014 (6) |
O151 | 0.44 (3) | 0.52 (5) | 0.51 (5) | −0.20 (3) | −0.36 (4) | 0.10 (4) |
N82 | 0.081 (10) | 0.046 (5) | 0.049 (8) | −0.012 (5) | −0.029 (7) | −0.012 (5) |
C92 | 0.074 (10) | 0.059 (8) | 0.034 (8) | 0.002 (7) | −0.007 (9) | −0.012 (6) |
C192 | 0.09 (2) | 0.112 (16) | 0.049 (10) | 0.071 (11) | −0.027 (12) | −0.016 (10) |
S112 | 0.090 (2) | 0.136 (3) | 0.074 (2) | −0.036 (2) | −0.0007 (18) | −0.054 (2) |
C122 | 0.053 (9) | 0.104 (12) | 0.058 (11) | −0.026 (7) | −0.012 (9) | −0.021 (9) |
C132 | 0.095 (7) | 0.154 (9) | 0.105 (7) | −0.047 (7) | −0.007 (6) | −0.062 (7) |
C142 | 0.102 (9) | 0.069 (6) | 0.124 (10) | −0.036 (5) | −0.047 (7) | −0.014 (6) |
O152 | 0.44 (3) | 0.52 (5) | 0.51 (5) | −0.20 (3) | −0.36 (4) | 0.10 (4) |
Geometric parameters (Å, º) top
C11—O11 | 1.263 (5) | C4—C5 | 1.410 (6) |
C11—C12 | 1.430 (6) | N4—H4A | 0.8600 |
C11—C16 | 1.445 (6) | N4—H4B | 0.8600 |
C12—C13 | 1.368 (6) | C5—C6 | 1.353 (6) |
C12—N11 | 1.451 (6) | C5—C7 | 1.502 (7) |
C13—C14 | 1.371 (7) | C6—H6 | 0.9300 |
C13—H13 | 0.9300 | C7—N82 | 1.496 (18) |
C14—C15 | 1.369 (7) | C7—N81 | 1.57 (2) |
C14—N12 | 1.445 (7) | C7—H7A | 0.9700 |
C15—C16 | 1.354 (6) | C7—H7B | 0.9700 |
C15—H15 | 0.9300 | C7—H7C | 0.9700 |
C16—N13 | 1.448 (7) | C7—H7D | 0.9700 |
N11—O13 | 1.196 (5) | N81—C121 | 1.30 (4) |
N11—O12 | 1.214 (6) | N81—C91 | 1.432 (16) |
N12—O14 | 1.219 (8) | C91—C101 | 1.29 (3) |
N12—O15 | 1.230 (7) | C91—C191 | 1.50 (2) |
N13—O17 | 1.173 (7) | C191—H19A | 0.9600 |
N13—O161 | 1.196 (18) | C191—H19B | 0.9600 |
N13—O16 | 1.233 (9) | C191—H19C | 0.9600 |
O16—O161 | 0.965 (18) | C101—C131 | 1.53 (2) |
C21—O21 | 1.242 (6) | C101—S111 | 1.73 (2) |
C21—C26 | 1.441 (7) | S111—C121 | 1.81 (3) |
C21—C22 | 1.447 (8) | C121—H12A | 0.9300 |
C22—C23 | 1.362 (7) | C131—C141 | 1.458 (9) |
C22—N21 | 1.469 (8) | C131—H13A | 0.9700 |
C23—C24 | 1.390 (7) | C131—H13B | 0.9700 |
C23—H23 | 0.9300 | C141—O151 | 1.380 (10) |
C24—C25 | 1.367 (8) | C141—H14A | 0.9700 |
C24—N22 | 1.459 (6) | C141—H14B | 0.9700 |
C25—C26 | 1.370 (7) | O151—H151 | 1.12 (4) |
C25—H25 | 0.9300 | N82—C92 | 1.30 (2) |
C26—N23 | 1.453 (8) | N82—C122 | 1.30 (3) |
N21—O231 | 1.119 (18) | C92—C102 | 1.37 (4) |
N21—O22 | 1.205 (7) | C92—C192 | 1.48 (4) |
N21—O23 | 1.338 (12) | C192—H19D | 0.9600 |
N22—O24 | 1.218 (7) | C192—H19E | 0.9600 |
N22—O25 | 1.226 (7) | C192—H19F | 0.9600 |
N23—O27 | 1.206 (6) | C102—C132 | 1.50 (3) |
N23—O26 | 1.234 (7) | C102—S112 | 1.82 (3) |
O23—O231 | 1.125 (16) | S112—C122 | 1.675 (17) |
N1—C2 | 1.340 (5) | C122—H12B | 0.9300 |
N1—C6 | 1.345 (5) | C132—C142 | 1.557 (9) |
N1—H1 | 0.8600 | C132—H13C | 0.9700 |
C2—N3 | 1.305 (5) | C132—H13D | 0.9700 |
C2—C3 | 1.492 (6) | C142—O152 | 1.417 (10) |
C3—H3B | 0.9600 | C142—H14C | 0.9700 |
C3—H3A | 0.9600 | C142—H14D | 0.9700 |
C3—H3C | 0.9600 | C142—H151 | 0.682 (14) |
N3—C4 | 1.354 (5) | O152—H152 | 1.11 (5) |
C4—N4 | 1.319 (5) | | |
| | | |
O11—C11—C12 | 126.5 (4) | N82—C7—C5 | 113.5 (5) |
O11—C11—C16 | 121.9 (4) | C5—C7—N81 | 109.6 (6) |
C12—C11—C16 | 111.6 (4) | C5—C7—H7A | 109.8 |
C13—C12—C11 | 123.2 (5) | N81—C7—H7A | 109.8 |
C13—C12—N11 | 117.2 (5) | N82—C7—H7B | 132.6 |
C11—C12—N11 | 119.6 (4) | C5—C7—H7B | 109.8 |
C12—C13—C14 | 120.8 (5) | N81—C7—H7B | 109.8 |
C12—C13—H13 | 119.6 | H7A—C7—H7B | 108.2 |
C14—C13—H13 | 119.6 | N82—C7—H7C | 108.3 |
C15—C14—C13 | 120.0 (4) | C5—C7—H7C | 109.3 |
C15—C14—N12 | 120.3 (5) | N81—C7—H7C | 76.0 |
C13—C14—N12 | 119.6 (6) | H7A—C7—H7C | 135.3 |
C16—C15—C14 | 119.2 (5) | N82—C7—H7D | 109.3 |
C16—C15—H15 | 120.4 | C5—C7—H7D | 108.6 |
C14—C15—H15 | 120.4 | N81—C7—H7D | 137.6 |
C15—C16—C11 | 125.1 (5) | H7B—C7—H7D | 73.1 |
C15—C16—N13 | 117.4 (5) | H7C—C7—H7D | 107.7 |
C11—C16—N13 | 117.5 (4) | C121—N81—C91 | 115 (2) |
O13—N11—O12 | 122.8 (5) | C121—N81—C7 | 130.2 (19) |
O13—N11—C12 | 118.7 (5) | C91—N81—C7 | 114.3 (19) |
O12—N11—C12 | 118.4 (5) | C101—C91—N81 | 114.6 (19) |
O14—N12—O15 | 123.6 (6) | C101—C91—C191 | 122.5 (14) |
O14—N12—C14 | 118.7 (7) | N81—C91—C191 | 122.9 (17) |
O15—N12—C14 | 117.7 (7) | C91—C191—H19A | 109.5 |
O17—N13—O161 | 114.2 (13) | C91—C191—H19B | 109.5 |
O17—N13—O16 | 117.6 (7) | H19A—C191—H19B | 109.5 |
O17—N13—C16 | 119.9 (5) | C91—C191—H19C | 109.5 |
O161—N13—C16 | 115.5 (10) | H19A—C191—H19C | 109.5 |
O16—N13—C16 | 120.6 (7) | H19B—C191—H19C | 109.5 |
O21—C21—C26 | 124.4 (6) | C91—C101—C131 | 128.7 (16) |
O21—C21—C22 | 123.8 (5) | C91—C101—S111 | 111.3 (14) |
C26—C21—C22 | 111.8 (4) | C131—C101—S111 | 119.7 (13) |
C23—C22—C21 | 123.6 (5) | C101—S111—C121 | 90.7 (13) |
C23—C22—N21 | 116.7 (6) | N81—C121—S111 | 108 (2) |
C21—C22—N21 | 119.7 (5) | N81—C121—H12A | 126.0 |
C22—C23—C24 | 119.8 (6) | S111—C121—H12A | 126.0 |
C22—C23—H23 | 120.1 | C141—C131—C101 | 114.4 (12) |
C24—C23—H23 | 120.1 | C141—C131—H13A | 108.7 |
C25—C24—C23 | 120.9 (5) | C101—C131—H13A | 108.7 |
C25—C24—N22 | 120.4 (6) | C141—C131—H13B | 108.7 |
C23—C24—N22 | 118.6 (6) | C101—C131—H13B | 108.7 |
C24—C25—C26 | 119.0 (5) | H13A—C131—H13B | 107.6 |
C24—C25—H25 | 120.5 | O151—C141—C131 | 102.5 (15) |
C26—C25—H25 | 120.5 | O151—C141—H14A | 111.3 |
C25—C26—C21 | 124.8 (5) | C131—C141—H14A | 111.3 |
C25—C26—N23 | 115.3 (5) | O151—C141—H14B | 111.3 |
C21—C26—N23 | 119.8 (5) | C131—C141—H14B | 111.3 |
O231—N21—O22 | 121.1 (12) | H14A—C141—H14B | 109.2 |
O22—N21—O23 | 117.8 (8) | C141—O151—H151 | 94 (2) |
O231—N21—C22 | 110.5 (10) | C92—N82—C122 | 117 (2) |
O22—N21—C22 | 118.3 (7) | C92—N82—C7 | 115.8 (19) |
O23—N21—C22 | 119.3 (7) | C122—N82—C7 | 126.7 (14) |
O24—N22—O25 | 124.6 (5) | N82—C92—C102 | 116 (3) |
O24—N22—C24 | 118.5 (6) | N82—C92—C192 | 133 (3) |
O25—N22—C24 | 116.9 (6) | C102—C92—C192 | 111 (2) |
O27—N23—O26 | 122.5 (7) | C92—C192—H19D | 109.5 |
O27—N23—C26 | 120.0 (6) | C92—C192—H19E | 109.5 |
O26—N23—C26 | 117.4 (5) | H19D—C192—H19E | 109.5 |
O231—O23—N21 | 53.2 (11) | C92—C192—H19F | 109.5 |
C2—N1—C6 | 121.2 (4) | H19D—C192—H19F | 109.5 |
C2—N1—H1 | 119.4 | H19E—C192—H19F | 109.5 |
C6—N1—H1 | 119.4 | C92—C102—C132 | 140 (2) |
N3—C2—N1 | 121.5 (4) | C92—C102—S112 | 104.5 (19) |
N3—C2—C3 | 120.7 (4) | C132—C102—S112 | 115.7 (19) |
N1—C2—C3 | 117.8 (4) | C122—S112—C102 | 91.0 (12) |
C2—C3—H3B | 109.5 | N82—C122—S112 | 111.1 (14) |
C2—C3—H3A | 109.5 | N82—C122—H12B | 124.5 |
H3B—C3—H3A | 109.5 | S112—C122—H12B | 124.5 |
C2—C3—H3C | 109.5 | C102—C132—C142 | 145.3 (15) |
H3B—C3—H3C | 109.5 | C102—C132—H13C | 100.5 |
H3A—C3—H3C | 109.5 | C142—C132—H13C | 100.5 |
C2—N3—C4 | 119.2 (4) | C102—C132—H13D | 100.5 |
N4—C4—N3 | 116.3 (4) | C142—C132—H13D | 100.5 |
N4—C4—C5 | 122.6 (4) | H13C—C132—H13D | 104.3 |
N3—C4—C5 | 121.1 (4) | O152—C142—C132 | 101.1 (7) |
C4—N4—H4A | 120.0 | O152—C142—H14C | 111.6 |
C4—N4—H4B | 120.0 | C132—C142—H14C | 111.6 |
H4A—N4—H4B | 120.0 | O152—C142—H14D | 111.6 |
C6—C5—C4 | 116.8 (4) | C132—C142—H14D | 111.6 |
C6—C5—C7 | 123.9 (4) | H14C—C142—H14D | 109.4 |
C4—C5—C7 | 119.2 (4) | O152—C142—H151 | 151 (2) |
N1—C6—C5 | 120.2 (4) | C132—C142—H151 | 103.3 (14) |
N1—C6—H6 | 119.9 | H14C—C142—H151 | 73.4 |
C5—C6—H6 | 119.9 | C142—O152—H152 | 89 (2) |
| | | |
O11—C11—C12—C13 | 178.8 (4) | C21—C26—N23—O26 | 157.9 (6) |
C16—C11—C12—C13 | −1.6 (6) | O22—N21—O23—O231 | −109.7 (15) |
O11—C11—C12—N11 | −0.6 (7) | C22—N21—O23—O231 | 94.9 (14) |
C16—C11—C12—N11 | 179.0 (4) | O22—N21—O231—O23 | 103.4 (15) |
C11—C12—C13—C14 | 0.1 (7) | C22—N21—O231—O23 | −111.9 (11) |
N11—C12—C13—C14 | 179.5 (4) | C6—N1—C2—N3 | −1.9 (7) |
C12—C13—C14—C15 | 2.1 (7) | C6—N1—C2—C3 | 177.6 (4) |
C12—C13—C14—N12 | −176.6 (4) | N1—C2—N3—C4 | 2.3 (7) |
C13—C14—C15—C16 | −2.7 (7) | C3—C2—N3—C4 | −177.1 (4) |
N12—C14—C15—C16 | 176.1 (4) | C2—N3—C4—N4 | 178.2 (4) |
C14—C15—C16—C11 | 1.1 (7) | C2—N3—C4—C5 | −0.9 (7) |
C14—C15—C16—N13 | −178.4 (4) | N4—C4—C5—C6 | 180.0 (5) |
O11—C11—C16—C15 | −179.3 (4) | N3—C4—C5—C6 | −1.0 (7) |
C12—C11—C16—C15 | 1.0 (6) | N4—C4—C5—C7 | 2.4 (8) |
O11—C11—C16—N13 | 0.2 (6) | N3—C4—C5—C7 | −178.6 (5) |
C12—C11—C16—N13 | −179.5 (4) | C2—N1—C6—C5 | −0.1 (7) |
C13—C12—N11—O13 | 17.4 (7) | C4—C5—C6—N1 | 1.5 (8) |
C11—C12—N11—O13 | −163.1 (5) | C7—C5—C6—N1 | 179.0 (6) |
C13—C12—N11—O12 | −159.1 (5) | C6—C5—C7—N82 | 0.4 (11) |
C11—C12—N11—O12 | 20.4 (7) | C4—C5—C7—N82 | 177.8 (8) |
C15—C14—N12—O14 | −172.2 (6) | C6—C5—C7—N81 | 39.9 (11) |
C13—C14—N12—O14 | 6.6 (8) | C4—C5—C7—N81 | −142.7 (8) |
C15—C14—N12—O15 | 7.7 (7) | N82—C7—N81—C121 | −171 (2) |
C13—C14—N12—O15 | −173.5 (5) | C5—C7—N81—C121 | 85.3 (2) |
C15—C16—N13—O17 | 116.2 (7) | N82—C7—N81—C91 | 0.3 (7) |
C11—C16—N13—O17 | −63.3 (7) | C5—C7—N81—C91 | −103.0 (9) |
C15—C16—N13—O161 | −100.9 (14) | C121—N81—C91—C101 | −4.3 (18) |
C11—C16—N13—O161 | 79.6 (14) | C7—N81—C91—C101 | −177.3 (11) |
C15—C16—N13—O16 | −47.7 (9) | C121—N81—C91—C191 | 177.7 (15) |
C11—C16—N13—O16 | 132.8 (8) | C7—N81—C91—C191 | 4.7 (15) |
O17—N13—O16—O161 | 98.3 (18) | N81—C91—C101—C131 | 175.1 (15) |
C16—N13—O16—O161 | −97.4 (17) | C191—C91—C101—C131 | −7 (3) |
O17—N13—O161—O16 | −105.9 (16) | N81—C91—C101—S111 | 1.8 (16) |
C16—N13—O161—O16 | 109.1 (13) | C191—C91—C101—S111 | 179.8 (12) |
O21—C21—C22—C23 | −178.8 (5) | C91—C101—S111—C121 | 0.5 (13) |
C26—C21—C22—C23 | −0.2 (7) | C131—C101—S111—C121 | −173.5 (14) |
O21—C21—C22—N21 | 2.2 (8) | C91—N81—C121—S111 | 4.4 (16) |
C26—C21—C22—N21 | −179.3 (5) | C7—N81—C121—S111 | 176.0 (9) |
C21—C22—C23—C24 | 0.7 (8) | C101—S111—C121—N81 | −2.9 (13) |
N21—C22—C23—C24 | 179.8 (5) | C91—C101—C131—C141 | 139.0 (16) |
C22—C23—C24—C25 | −0.3 (8) | S111—C101—C131—C141 | −48.1 (2) |
C22—C23—C24—N22 | −177.4 (4) | C101—C131—C141—O151 | 38 (2) |
C23—C24—C25—C26 | −0.6 (8) | C5—C7—N82—C92 | 91.2 (10) |
N22—C24—C25—C26 | 176.4 (4) | N81—C7—N82—C92 | −0.5 (11) |
C24—C25—C26—C21 | 1.2 (8) | C5—C7—N82—C122 | −93.8 (2) |
C24—C25—C26—N23 | −177.1 (5) | N81—C7—N82—C122 | 175 (2) |
O21—C21—C26—C25 | 177.8 (5) | C122—N82—C92—C102 | −2 (2) |
C22—C21—C26—C25 | −0.7 (7) | C7—N82—C92—C102 | 173.2 (15) |
O21—C21—C26—N23 | −4.0 (8) | C122—N82—C92—C192 | 179 (2) |
C22—C21—C26—N23 | 177.5 (5) | C7—N82—C92—C192 | −6 (2) |
C23—C22—N21—O231 | 51.2 (15) | N82—C92—C102—C132 | −176 (3) |
C21—C22—N21—O231 | −129.7 (14) | C192—C92—C102—C132 | 3 (4) |
C23—C22—N21—O22 | −163.0 (6) | N82—C92—C102—S112 | 4 (2) |
C21—C22—N21—O22 | 16.1 (9) | C192—C92—C102—S112 | −176.9 (15) |
C23—C22—N21—O23 | −7.7 (1) | C92—C102—S112—C122 | −3.7 (17) |
C21—C22—N21—O23 | 171.3 (1) | C132—C102—S112—C122 | 176.4 (19) |
C25—C24—N22—O24 | −172.0 (5) | C92—N82—C122—S112 | −1.1 (18) |
C23—C24—N22—O24 | 5.1 (7) | C7—N82—C122—S112 | −176.0 (8) |
C25—C24—N22—O25 | 7.4 (8) | C102—S112—C122—N82 | 2.8 (16) |
C23—C24—N22—O25 | −175.5 (5) | C92—C102—C132—C142 | −128 (3) |
C25—C26—N23—O27 | 159.4 (6) | S112—C102—C132—C142 | 52 (4) |
C21—C26—N23—O27 | −18.9 (9) | C102—C132—C142—O152 | −6 (4) |
C25—C26—N23—O26 | −23.7 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···O12i | 0.86 | 2.55 | 3.062 (7) | 119 |
N4—H4B···O11i | 0.86 | 2.07 | 2.885 (5) | 159 |
N4—H4A···O11ii | 0.86 | 2.28 | 3.102 (5) | 161 |
N1—H1···O27iii | 0.86 | 2.57 | 3.348 (7) | 151 |
N1—H1···O21iii | 0.86 | 1.99 | 2.667 (5) | 135 |
O151—H151···O14iv | 1.12 (4) | 2.387 (5) | 3.33 (4) | 140.1 (1) |
O152—H152···O26 | 1.11 (5) | 2.369 (6) | 3.40 (5) | 154.4 (1) |
C6—H6···O21iii | 0.93 | 2.62 | 2.993 (6) | 104 |
C3—H3A···O27iii | 0.96 | 2.29 | 3.205 (7) | 159 |
C3—H3C···O16v | 0.96 | 2.37 | 3.307 (10) | 167 |
C121—H12A···O12iii | 0.93 | 2.65 | 3.33 (3) | 131 |
C122—H12B···O151vi | 0.93 | 2.58 | 3.39 (3) | 146 |
Symmetry codes: (i) x−1, y+1, z−1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) x, y, z−1; (vi) x−1, y, z. |
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