Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601720X/lh2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601720X/lh2041Isup2.hkl |
CCDC reference: 610831
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.
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 |
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 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 |
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. |
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 |
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) |
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) |
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. |