In the title inclusion structure, C20H18N4O4S2·0.5C3H6O, the phenyl groups form hydrophobic channels along [001], hosting acetone molecules. The phenylsulfonyl substituent group and the methyl group on the cyclopropane ring are syn with respect to each other, and the two phenylsulfonyl groups are positioned on the same side of the triazolopyridazine ring.
Supporting information
CCDC reference: 277711
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.058
- wR factor = 0.121
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.92 Ratio
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.158
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.32 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C32
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01
PLAT751_ALERT_4_C Bond Calc 0.96000, Rep 0.959(8) ...... Senseless su
C31 -H31A 1.555 1.555
PLAT751_ALERT_4_C Bond Calc 0.96000, Rep 0.958(9) ...... Senseless su
C31 -H31B 1.555 1.555
PLAT751_ALERT_4_C Bond Calc 0.96000, Rep 0.963(9) ...... Senseless su
C31 -H31C 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 110.00, Rep 109.5(7) ...... Senseless su
C32 -C31 -H31A 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 110.00, Rep 109.5(8) ...... Senseless su
C32 -C31 -H31B 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 110.00, Rep 109.8(8) ...... Senseless su
H31A -C31 -H31B 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 109.00, Rep 109.2(8) ...... Senseless su
C32 -C31 -H31C 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 109.00, Rep 109.4(9) ...... Senseless su
H31A -C31 -H31C 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 109.00, Rep 109.4(8) ...... Senseless su
H31B -C31 -H31C 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C3 H6 O
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C21.5 H21 N4 O4.5 S2
Atom count from _chemical_formula_moiety:C20 H18 N4 O4 S2
1 ALERT level A = In general: serious problem
5 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
11 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989) and Mercury (Version 1.3;
Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
6a-Methyl-7-phenylsulfonyl-6-phenylsulfonylmethyl-7,7a-dihydro-6aH–
cyclopropa[
d][1,2,3]triazolo[4,3-
b]pyridazine:acetone solvate
2:1
top
Crystal data top
C20H18N4O4S2·0.5C3H6O | F(000) = 1968 |
Mr = 471.54 | Dx = 1.385 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1368 reflections |
a = 28.242 (6) Å | θ = 2.4–28.1° |
b = 9.5962 (19) Å | µ = 0.27 mm−1 |
c = 21.108 (4) Å | T = 293 K |
β = 127.74 (3)° | Plate, colourless |
V = 4524 (2) Å3 | 0.22 × 0.13 × 0.05 mm |
Z = 8 | |
Data collection top
Kuma KM-4 CCD diffractometer | 1569 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.158 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −33→32 |
16780 measured reflections | k = −8→11 |
3985 independent reflections | l = −24→25 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2)] |
3985 reflections | (Δ/σ)max < 0.001 |
300 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 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 | |
N1 | 0.3223 (2) | 0.6313 (5) | 0.0841 (3) | 0.0464 (14) | |
N2 | 0.2701 (3) | 0.5526 (5) | 0.0283 (3) | 0.0513 (14) | |
C3 | 0.2337 (3) | 0.5754 (7) | 0.0456 (4) | 0.0457 (19) | |
H3 | 0.199 (2) | 0.535 (4) | 0.018 (3) | 0.024 (16)* | |
N4 | 0.2575 (2) | 0.6628 (4) | 0.1073 (3) | 0.0324 (12) | |
N5 | 0.23116 (19) | 0.7049 (4) | 0.1419 (3) | 0.0316 (12) | |
C6 | 0.2610 (3) | 0.7943 (5) | 0.1995 (3) | 0.0279 (14) | |
C7 | 0.3221 (2) | 0.8477 (5) | 0.2338 (3) | 0.0268 (14) | |
C8 | 0.3489 (2) | 0.7937 (6) | 0.1937 (3) | 0.0339 (15) | |
H8A | 0.3924 | 0.7801 | 0.2280 | 0.041* | |
C9 | 0.3126 (3) | 0.6944 (6) | 0.1299 (3) | 0.0320 (15) | |
C10 | 0.3632 (2) | 0.8757 (5) | 0.3246 (3) | 0.0395 (16) | |
H101 | 0.4024 | 0.8847 | 0.3387 | 0.051* | |
H102 | 0.3622 | 0.7963 | 0.3514 | 0.051* | |
H103 | 0.3538 | 0.9583 | 0.3407 | 0.051* | |
C11 | 0.2297 (2) | 0.8435 (5) | 0.2329 (3) | 0.0338 (15) | |
H111 | 0.2590 | 0.8798 | 0.2865 | 0.041* | |
H112 | 0.2096 | 0.7653 | 0.2364 | 0.041* | |
S12 | 0.17616 (7) | 0.97576 (15) | 0.17108 (9) | 0.0407 (5) | |
O13 | 0.15302 (16) | 1.0249 (3) | 0.2117 (2) | 0.0530 (12) | |
O14 | 0.20384 (16) | 1.0737 (3) | 0.1514 (2) | 0.0512 (11) | |
C15 | 0.1180 (3) | 0.8916 (6) | 0.0819 (3) | 0.0430 (17) | |
C16 | 0.1196 (3) | 0.8810 (6) | 0.0190 (4) | 0.0488 (17) | |
H16A | 0.1508 | 0.9222 | 0.0222 | 0.059* | |
C17 | 0.0758 (3) | 0.8105 (7) | −0.0491 (4) | 0.065 (2) | |
H17A | 0.0773 | 0.8035 | −0.0918 | 0.078* | |
C18 | 0.0299 (3) | 0.7505 (9) | −0.0533 (5) | 0.109 (3) | |
H18A | −0.0004 | 0.7035 | −0.0995 | 0.131* | |
C19 | 0.0284 (3) | 0.7595 (9) | 0.0093 (5) | 0.118 (3) | |
H19A | −0.0030 | 0.7177 | 0.0054 | 0.142* | |
C20 | 0.0720 (3) | 0.8287 (8) | 0.0789 (4) | 0.081 (2) | |
H20A | 0.0709 | 0.8332 | 0.1220 | 0.097* | |
C21 | 0.3267 (2) | 0.9409 (5) | 0.1795 (3) | 0.0285 (14) | |
H21A | 0.2887 | 0.9584 | 0.1266 | 0.034* | |
S22 | 0.37809 (8) | 1.08033 (16) | 0.21937 (9) | 0.0393 (5) | |
O23 | 0.35305 (18) | 1.1943 (4) | 0.2346 (2) | 0.0605 (13) | |
O24 | 0.43637 (17) | 1.0294 (4) | 0.2835 (2) | 0.0535 (12) | |
C25 | 0.3794 (3) | 1.1288 (6) | 0.1399 (3) | 0.0343 (15) | |
C26 | 0.4209 (3) | 1.0718 (6) | 0.1334 (3) | 0.0504 (17) | |
H26A | 0.4475 | 1.0042 | 0.1694 | 0.060* | |
C27 | 0.4223 (3) | 1.1168 (8) | 0.0722 (4) | 0.069 (2) | |
H27A | 0.4503 | 1.0799 | 0.0671 | 0.083* | |
C28 | 0.3827 (3) | 1.2154 (7) | 0.0195 (4) | 0.065 (2) | |
H28A | 0.3842 | 1.2459 | −0.0210 | 0.078* | |
C29 | 0.3405 (3) | 1.2705 (6) | 0.0251 (4) | 0.058 (2) | |
H29A | 0.3133 | 1.3367 | −0.0116 | 0.070* | |
C30 | 0.3390 (3) | 1.2267 (6) | 0.0854 (4) | 0.0490 (18) | |
H30A | 0.3106 | 1.2631 | 0.0897 | 0.059* | |
O32 | 0.0000 | 0.8250 (8) | −0.2500 | 0.089 (3) | |
C32 | 0.0000 | 0.9497 (13) | −0.2500 | 0.070 (3) | |
C31 | 0.0323 (4) | 1.0308 (9) | −0.2723 (5) | 0.122 (3) | |
H31A | 0.0464 | 0.9693 | −0.2932 | 0.183* | |
H31B | 0.0654 | 1.0782 | −0.2261 | 0.183* | |
H31C | 0.0054 | 1.0981 | −0.3127 | 0.183* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.054 (4) | 0.053 (4) | 0.039 (3) | 0.001 (3) | 0.033 (3) | −0.006 (3) |
N2 | 0.066 (4) | 0.052 (4) | 0.049 (4) | 0.007 (3) | 0.042 (4) | −0.009 (3) |
C3 | 0.044 (5) | 0.037 (5) | 0.041 (5) | −0.012 (4) | 0.018 (4) | −0.012 (4) |
N4 | 0.033 (3) | 0.033 (3) | 0.029 (3) | −0.003 (3) | 0.018 (3) | −0.006 (2) |
N5 | 0.035 (3) | 0.035 (3) | 0.032 (3) | −0.003 (3) | 0.024 (3) | −0.005 (2) |
C6 | 0.034 (4) | 0.029 (4) | 0.029 (4) | 0.009 (3) | 0.023 (3) | 0.012 (3) |
C7 | 0.027 (4) | 0.028 (3) | 0.025 (3) | −0.004 (3) | 0.015 (3) | 0.003 (3) |
C8 | 0.030 (4) | 0.047 (4) | 0.040 (4) | 0.001 (3) | 0.029 (4) | 0.001 (3) |
C9 | 0.036 (4) | 0.037 (4) | 0.024 (4) | 0.002 (3) | 0.019 (4) | 0.001 (3) |
C10 | 0.036 (4) | 0.053 (4) | 0.023 (4) | −0.006 (3) | 0.015 (3) | 0.003 (3) |
C11 | 0.030 (4) | 0.046 (4) | 0.031 (4) | −0.008 (3) | 0.022 (3) | −0.003 (3) |
S12 | 0.0483 (12) | 0.0394 (10) | 0.0492 (11) | −0.0012 (9) | 0.0374 (10) | −0.0035 (9) |
O13 | 0.066 (3) | 0.048 (3) | 0.070 (3) | −0.002 (2) | 0.055 (3) | −0.015 (2) |
O14 | 0.068 (3) | 0.036 (2) | 0.065 (3) | −0.015 (2) | 0.049 (3) | −0.002 (2) |
C15 | 0.043 (5) | 0.050 (4) | 0.029 (4) | −0.003 (3) | 0.019 (4) | 0.003 (3) |
C16 | 0.048 (5) | 0.057 (4) | 0.055 (5) | −0.005 (4) | 0.038 (4) | 0.005 (4) |
C17 | 0.047 (5) | 0.108 (6) | 0.028 (5) | −0.011 (5) | 0.018 (4) | −0.012 (4) |
C18 | 0.067 (6) | 0.203 (10) | 0.046 (6) | −0.066 (6) | 0.028 (5) | −0.037 (6) |
C19 | 0.065 (7) | 0.223 (10) | 0.075 (7) | −0.072 (6) | 0.047 (6) | −0.036 (7) |
C20 | 0.064 (6) | 0.140 (7) | 0.052 (5) | −0.036 (5) | 0.042 (5) | −0.010 (5) |
C21 | 0.022 (3) | 0.047 (4) | 0.020 (3) | −0.008 (3) | 0.014 (3) | −0.005 (3) |
S22 | 0.0418 (12) | 0.0493 (11) | 0.0387 (11) | −0.0137 (10) | 0.0307 (10) | −0.0094 (9) |
O23 | 0.088 (4) | 0.050 (3) | 0.090 (4) | −0.017 (2) | 0.078 (3) | −0.029 (2) |
O24 | 0.037 (3) | 0.086 (3) | 0.026 (2) | −0.020 (2) | 0.013 (2) | 0.001 (2) |
C25 | 0.038 (4) | 0.038 (4) | 0.034 (4) | −0.003 (3) | 0.025 (4) | −0.002 (3) |
C26 | 0.040 (4) | 0.076 (5) | 0.049 (4) | 0.015 (4) | 0.034 (4) | 0.008 (4) |
C27 | 0.060 (5) | 0.114 (7) | 0.060 (5) | 0.015 (5) | 0.051 (5) | 0.012 (5) |
C28 | 0.083 (6) | 0.085 (6) | 0.053 (5) | −0.001 (5) | 0.055 (5) | 0.016 (4) |
C29 | 0.067 (6) | 0.048 (5) | 0.066 (6) | 0.009 (4) | 0.044 (5) | 0.013 (4) |
C30 | 0.061 (5) | 0.050 (5) | 0.060 (5) | −0.001 (4) | 0.049 (5) | 0.002 (4) |
O32 | 0.117 (7) | 0.064 (5) | 0.053 (5) | 0.000 | 0.035 (5) | 0.000 |
C32 | 0.060 (8) | 0.086 (10) | 0.049 (7) | 0.000 | 0.025 (6) | 0.000 |
C31 | 0.116 (8) | 0.119 (7) | 0.151 (9) | −0.019 (6) | 0.092 (7) | −0.002 (6) |
Geometric parameters (Å, º) top
N1—C9 | 1.305 (6) | C17—C18 | 1.372 (8) |
N1—N2 | 1.416 (6) | C17—H17A | 0.9300 |
N2—C3 | 1.303 (7) | C18—C19 | 1.351 (9) |
C3—N4 | 1.334 (7) | C18—H18A | 0.9300 |
C3—H3 | 0.88 (4) | C19—C20 | 1.379 (9) |
N4—C9 | 1.354 (6) | C19—H19A | 0.9300 |
N4—N5 | 1.383 (5) | C20—H20A | 0.9300 |
N5—C6 | 1.294 (6) | C21—S22 | 1.764 (5) |
C6—C7 | 1.495 (6) | C21—H21A | 0.9800 |
C6—C11 | 1.505 (6) | S22—O24 | 1.433 (4) |
C7—C21 | 1.518 (6) | S22—O23 | 1.441 (3) |
C7—C8 | 1.529 (6) | S22—C25 | 1.764 (5) |
C7—C10 | 1.540 (6) | C25—C26 | 1.373 (6) |
C8—C9 | 1.443 (7) | C25—C30 | 1.379 (7) |
C8—C21 | 1.500 (6) | C26—C27 | 1.386 (7) |
C8—H8A | 0.9800 | C26—H26A | 0.9300 |
C10—H101 | 0.9600 | C27—C28 | 1.365 (8) |
C10—H102 | 0.9600 | C27—H27A | 0.9300 |
C10—H103 | 0.9600 | C28—C29 | 1.373 (7) |
C11—S12 | 1.784 (5) | C28—H28A | 0.9300 |
C11—H111 | 0.9700 | C29—C30 | 1.364 (7) |
C11—H112 | 0.9700 | C29—H29A | 0.9300 |
S12—O14 | 1.438 (3) | C30—H30A | 0.9300 |
S12—O13 | 1.439 (3) | O32—C32 | 1.197 (10) |
S12—C15 | 1.763 (6) | C32—C31i | 1.478 (8) |
C15—C16 | 1.360 (7) | C32—C31 | 1.478 (8) |
C15—C20 | 1.397 (7) | C31—H31A | 0.959 (8) |
C16—C17 | 1.369 (7) | C31—H31B | 0.958 (9) |
C16—H16A | 0.9300 | C31—H31C | 0.963 (9) |
| | | |
C9—N1—N2 | 106.2 (5) | C16—C17—C18 | 119.1 (7) |
C3—N2—N1 | 106.0 (5) | C16—C17—H17A | 120.4 |
N2—C3—N4 | 111.5 (6) | C18—C17—H17A | 120.4 |
N2—C3—H3 | 121 (3) | C19—C18—C17 | 120.3 (7) |
N4—C3—H3 | 128 (3) | C19—C18—H18A | 119.9 |
C3—N4—C9 | 105.6 (5) | C17—C18—H18A | 119.9 |
C3—N4—N5 | 125.9 (5) | C18—C19—C20 | 122.0 (7) |
C9—N4—N5 | 128.4 (5) | C18—C19—H19A | 119.0 |
C6—N5—N4 | 116.0 (4) | C20—C19—H19A | 119.0 |
N5—C6—C7 | 125.2 (5) | C19—C20—C15 | 117.2 (7) |
N5—C6—C11 | 114.6 (5) | C19—C20—H20A | 121.4 |
C7—C6—C11 | 120.2 (5) | C15—C20—H20A | 121.4 |
C6—C7—C21 | 116.3 (4) | C8—C21—C7 | 60.9 (3) |
C6—C7—C8 | 115.6 (4) | C8—C21—S22 | 119.8 (4) |
C21—C7—C8 | 59.0 (3) | C7—C21—S22 | 120.8 (4) |
C6—C7—C10 | 115.3 (4) | C8—C21—H21A | 114.9 |
C21—C7—C10 | 119.3 (4) | C7—C21—H21A | 114.9 |
C8—C7—C10 | 119.9 (5) | S22—C21—H21A | 114.9 |
C9—C8—C21 | 117.7 (5) | O24—S22—O23 | 119.0 (3) |
C9—C8—C7 | 115.5 (5) | O24—S22—C25 | 107.9 (3) |
C21—C8—C7 | 60.1 (3) | O23—S22—C25 | 108.1 (3) |
C9—C8—H8A | 117.1 | O24—S22—C21 | 109.0 (2) |
C21—C8—H8A | 117.1 | O23—S22—C21 | 108.0 (2) |
C7—C8—H8A | 117.1 | C25—S22—C21 | 103.7 (2) |
N1—C9—N4 | 110.7 (5) | C26—C25—C30 | 120.6 (5) |
N1—C9—C8 | 130.2 (6) | C26—C25—S22 | 120.4 (5) |
N4—C9—C8 | 119.0 (5) | C30—C25—S22 | 119.0 (5) |
C7—C10—H101 | 104.3 | C25—C26—C27 | 118.9 (6) |
C7—C10—H102 | 108.9 | C25—C26—H26A | 120.6 |
H101—C10—H102 | 109.5 | C27—C26—H26A | 120.6 |
C7—C10—H103 | 115.1 | C28—C27—C26 | 119.9 (6) |
H101—C10—H103 | 109.5 | C28—C27—H27A | 120.1 |
H102—C10—H103 | 109.5 | C26—C27—H27A | 120.1 |
C6—C11—S12 | 111.0 (4) | C27—C28—C29 | 121.3 (6) |
C6—C11—H111 | 109.4 | C27—C28—H28A | 119.4 |
S12—C11—H111 | 109.4 | C29—C28—H28A | 119.4 |
C6—C11—H112 | 109.4 | C30—C29—C28 | 119.0 (6) |
S12—C11—H112 | 109.4 | C30—C29—H29A | 120.5 |
H111—C11—H112 | 108.0 | C28—C29—H29A | 120.5 |
O14—S12—O13 | 118.9 (2) | C29—C30—C25 | 120.4 (6) |
O14—S12—C15 | 107.9 (3) | C29—C30—H30A | 119.8 |
O13—S12—C15 | 108.7 (3) | C25—C30—H30A | 119.8 |
O14—S12—C11 | 108.0 (2) | O32—C32—C31i | 121.8 (5) |
O13—S12—C11 | 106.8 (2) | O32—C32—C31 | 121.8 (5) |
C15—S12—C11 | 105.9 (3) | C31i—C32—C31 | 116.4 (11) |
C16—C15—C20 | 120.5 (6) | C32—C31—H31A | 109.5 (7) |
C16—C15—S12 | 120.7 (5) | C32—C31—H31B | 109.5 (8) |
C20—C15—S12 | 118.7 (5) | H31A—C31—H31B | 109.8 (8) |
C15—C16—C17 | 120.9 (6) | C32—C31—H31C | 109.2 (8) |
C15—C16—H16A | 119.6 | H31A—C31—H31C | 109.4 (9) |
C17—C16—H16A | 119.6 | H31B—C31—H31C | 109.4 (8) |
| | | |
C9—N1—N2—C3 | −0.1 (6) | O13—S12—C15—C20 | −28.3 (6) |
N1—N2—C3—N4 | 0.5 (7) | C11—S12—C15—C20 | 86.1 (6) |
N2—C3—N4—C9 | −0.7 (7) | C20—C15—C16—C17 | 1.1 (9) |
N2—C3—N4—N5 | −178.0 (5) | S12—C15—C16—C17 | 177.2 (5) |
C3—N4—N5—C6 | −177.6 (5) | C15—C16—C17—C18 | 0.2 (10) |
C9—N4—N5—C6 | 5.7 (7) | C16—C17—C18—C19 | −0.9 (13) |
N4—N5—C6—C7 | −3.7 (7) | C17—C18—C19—C20 | 0.3 (15) |
N4—N5—C6—C11 | 177.0 (4) | C18—C19—C20—C15 | 0.9 (13) |
N5—C6—C7—C21 | 68.7 (7) | C16—C15—C20—C19 | −1.6 (11) |
C11—C6—C7—C21 | −112.0 (5) | S12—C15—C20—C19 | −177.7 (6) |
N5—C6—C7—C8 | 2.3 (7) | C9—C8—C21—C7 | 105.0 (5) |
C11—C6—C7—C8 | −178.4 (4) | C9—C8—C21—S22 | −144.1 (4) |
N5—C6—C7—C10 | −144.5 (5) | C7—C8—C21—S22 | 110.9 (4) |
C11—C6—C7—C10 | 34.8 (6) | C6—C7—C21—C8 | −105.4 (5) |
C6—C7—C8—C9 | −2.1 (7) | C10—C7—C21—C8 | 109.2 (5) |
C21—C7—C8—C9 | −108.6 (5) | C6—C7—C21—S22 | 145.3 (4) |
C10—C7—C8—C9 | 143.1 (5) | C8—C7—C21—S22 | −109.3 (5) |
C6—C7—C8—C21 | 106.5 (5) | C10—C7—C21—S22 | −0.1 (7) |
C10—C7—C8—C21 | −108.2 (5) | C8—C21—S22—O24 | −20.0 (4) |
N2—N1—C9—N4 | −0.4 (6) | C7—C21—S22—O24 | 51.8 (5) |
N2—N1—C9—C8 | −176.1 (5) | C8—C21—S22—O23 | −150.7 (4) |
C3—N4—C9—N1 | 0.7 (6) | C7—C21—S22—O23 | −78.8 (5) |
N5—N4—C9—N1 | 177.8 (4) | C8—C21—S22—C25 | 94.7 (4) |
C3—N4—C9—C8 | 177.0 (5) | C7—C21—S22—C25 | 166.6 (4) |
N5—N4—C9—C8 | −5.9 (8) | O24—S22—C25—C26 | 23.3 (5) |
C21—C8—C9—N1 | 111.0 (6) | O23—S22—C25—C26 | 153.2 (4) |
C7—C8—C9—N1 | 179.1 (5) | C21—S22—C25—C26 | −92.3 (5) |
C21—C8—C9—N4 | −64.4 (6) | O24—S22—C25—C30 | −155.5 (4) |
C7—C8—C9—N4 | 3.7 (7) | O23—S22—C25—C30 | −25.5 (5) |
N5—C6—C11—S12 | −80.7 (5) | C21—S22—C25—C30 | 89.0 (5) |
C7—C6—C11—S12 | 100.0 (5) | C30—C25—C26—C27 | 1.5 (9) |
C6—C11—S12—O14 | −45.5 (4) | S22—C25—C26—C27 | −177.2 (5) |
C6—C11—S12—O13 | −174.5 (4) | C25—C26—C27—C28 | −0.5 (10) |
C6—C11—S12—C15 | 69.8 (5) | C26—C27—C28—C29 | −0.8 (11) |
O14—S12—C15—C16 | 25.4 (6) | C27—C28—C29—C30 | 0.9 (10) |
O13—S12—C15—C16 | 155.6 (5) | C28—C29—C30—C25 | 0.2 (9) |
C11—S12—C15—C16 | −90.1 (5) | C26—C25—C30—C29 | −1.4 (9) |
O14—S12—C15—C20 | −158.5 (5) | S22—C25—C30—C29 | 177.3 (5) |
Symmetry code: (i) −x, y, −z−1/2. |