The title compound, C
22H
16N
2S
2, has one and a half molecules in the asymmetric unit. Each molecule has a twist conformation and distorted
C2v symmetry. The supramolecular structure of the title compound is defined by C—H
N, π–π stacking and C—H
π interactions.
Supporting information
CCDC reference: 232138
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.060
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C8 = 7.58 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 = 7.59 su
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.733
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 = 5.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for S3 - C27 = 6.73 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 = 6.16 su
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S1
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S2
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S3
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C12
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C27
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C30
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C8 = 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 = 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C24 = 1.44 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
16 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
16 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
4,5-Bis(4-methylphenylsulfanyl)phthalonitrile
top
Crystal data top
C22H16N2S2 | F(000) = 2328 |
Mr = 372.49 | Dx = 1.289 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7445 reflections |
a = 27.347 (3) Å | θ = 1.6–24.6° |
b = 15.4675 (10) Å | µ = 0.29 mm−1 |
c = 15.5745 (17) Å | T = 293 K |
β = 119.093 (7)° | Tablet, colorless |
V = 5756.7 (9) Å3 | 0.38 × 0.28 × 0.17 mm |
Z = 12 | |
Data collection top
Stoe IPDS-II diffractometer | 5661 independent reflections |
Radiation source: fine-focus sealed tube | 2308 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.089 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
rotation method scans | h = −33→33 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.917, Tmax = 0.952 | l = −19→19 |
20063 measured reflections | |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 0.73 | w = 1/[σ2(Fo2) + (0.0153P)2] where P = (Fo2 + 2Fc2)/3 |
5661 reflections | (Δ/σ)max = 0.001 |
355 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.18 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) |
N3 | 0.08145 (9) | 0.22183 (16) | 0.81204 (18) | 0.0670 (7) | |
C23 | 0.05875 (11) | 0.15712 (19) | 0.79518 (19) | 0.0493 (7) | |
S1 | 0.25002 (3) | 0.30062 (5) | 1.22057 (5) | 0.0673 (2) | |
S2 | 0.12872 (3) | 0.33637 (5) | 1.06434 (6) | 0.0691 (2) | |
S3 | 0.06256 (4) | −0.18077 (5) | 0.79523 (6) | 0.0852 (3) | |
C5 | 0.18203 (10) | 0.35457 (16) | 1.03346 (18) | 0.0434 (7) | |
C4 | 0.17093 (10) | 0.38353 (15) | 0.94176 (19) | 0.0477 (7) | |
H4 | 0.1341 | 0.3942 | 0.8941 | 0.057* | |
C8 | 0.26875 (10) | 0.37842 (15) | 0.99033 (19) | 0.0415 (6) | |
C3 | 0.21357 (11) | 0.39699 (15) | 0.91958 (18) | 0.0431 (6) | |
C9 | 0.32236 (10) | 0.3219 (2) | 1.29693 (17) | 0.0470 (7) | |
C6 | 0.23728 (10) | 0.33732 (15) | 1.10482 (16) | 0.0418 (6) | |
C25 | 0.05779 (11) | −0.00157 (17) | 0.79429 (18) | 0.0527 (7) | |
H25 | 0.0966 | −0.0013 | 0.8241 | 0.063* | |
C12 | 0.43509 (11) | 0.3532 (2) | 1.42672 (19) | 0.0573 (8) | |
C24 | 0.02914 (9) | 0.07593 (16) | 0.77252 (18) | 0.0445 (6) | |
C7 | 0.27981 (10) | 0.34792 (15) | 1.08125 (18) | 0.0472 (7) | |
H7 | 0.3164 | 0.3342 | 1.1276 | 0.057* | |
C1 | 0.31370 (11) | 0.39155 (17) | 0.96823 (19) | 0.0528 (8) | |
C28 | 0.16218 (13) | −0.14520 (18) | 0.9566 (2) | 0.0681 (9) | |
H28 | 0.1424 | −0.1480 | 0.9910 | 0.082* | |
C14 | 0.35866 (12) | 0.25430 (18) | 1.34184 (19) | 0.0538 (7) | |
H14 | 0.3457 | 0.1976 | 1.3289 | 0.065* | |
C27 | 0.13467 (11) | −0.15411 (17) | 0.8570 (2) | 0.0577 (7) | |
C19 | −0.01318 (12) | 0.5129 (2) | 0.8556 (2) | 0.0557 (8) | |
C20 | −0.01626 (11) | 0.4254 (2) | 0.8436 (2) | 0.0619 (8) | |
H20 | −0.0484 | 0.4015 | 0.7924 | 0.074* | |
C18 | 0.03449 (14) | 0.54625 (18) | 0.9335 (2) | 0.0594 (8) | |
H18 | 0.0379 | 0.6057 | 0.9436 | 0.071* | |
C13 | 0.41418 (12) | 0.2708 (2) | 1.4059 (2) | 0.0612 (8) | |
H13 | 0.4383 | 0.2246 | 1.4361 | 0.073* | |
N2 | 0.19269 (10) | 0.45843 (16) | 0.75162 (18) | 0.0766 (8) | |
C16 | 0.07413 (10) | 0.40498 (19) | 0.98176 (19) | 0.0457 (7) | |
C17 | 0.07760 (11) | 0.4923 (2) | 0.9971 (2) | 0.0585 (8) | |
H17 | 0.1090 | 0.5158 | 1.0504 | 0.070* | |
C11 | 0.39800 (13) | 0.42032 (19) | 1.3807 (2) | 0.0638 (8) | |
H11 | 0.4112 | 0.4769 | 1.3930 | 0.077* | |
C2 | 0.20175 (11) | 0.43074 (17) | 0.8256 (2) | 0.0510 (7) | |
C26 | 0.02962 (10) | −0.07960 (17) | 0.77242 (19) | 0.0545 (7) | |
N1 | 0.34896 (11) | 0.40161 (16) | 0.95095 (19) | 0.0826 (8) | |
C10 | 0.34211 (12) | 0.40571 (19) | 1.3172 (2) | 0.0581 (8) | |
H10 | 0.3178 | 0.4520 | 1.2881 | 0.070* | |
C21 | 0.02649 (12) | 0.37119 (18) | 0.9045 (2) | 0.0558 (8) | |
H21 | 0.0232 | 0.3118 | 0.8935 | 0.067* | |
C32 | 0.16432 (17) | −0.1489 (2) | 0.8067 (2) | 0.0865 (10) | |
H32 | 0.1462 | −0.1549 | 0.7387 | 0.104* | |
C31 | 0.22104 (19) | −0.1346 (2) | 0.8581 (3) | 0.0943 (12) | |
H31 | 0.2407 | −0.1297 | 0.8235 | 0.113* | |
C29 | 0.21921 (13) | −0.13203 (18) | 1.0065 (2) | 0.0706 (9) | |
H29 | 0.2374 | −0.1262 | 1.0745 | 0.085* | |
C30 | 0.24958 (14) | −0.12737 (17) | 0.9581 (3) | 0.0717 (9) | |
C22 | −0.05986 (12) | 0.5717 (2) | 0.7863 (2) | 0.0859 (10) | |
H22A | −0.0541 | 0.6286 | 0.8141 | 0.129* | 0.50 |
H22B | −0.0950 | 0.5495 | 0.7762 | 0.129* | 0.50 |
H22C | −0.0601 | 0.5743 | 0.7245 | 0.129* | 0.50 |
H22D | −0.0854 | 0.5396 | 0.7291 | 0.129* | 0.50 |
H22E | −0.0445 | 0.6188 | 0.7670 | 0.129* | 0.50 |
H22F | −0.0794 | 0.5939 | 0.8187 | 0.129* | 0.50 |
C15 | 0.49632 (12) | 0.3696 (2) | 1.4969 (2) | 0.0973 (11) | |
H15A | 0.5008 | 0.4262 | 1.5250 | 0.146* | 0.50 |
H15B | 0.5171 | 0.3660 | 1.4620 | 0.146* | 0.50 |
H15C | 0.5100 | 0.3271 | 1.5483 | 0.146* | 0.50 |
H15D | 0.5178 | 0.3200 | 1.4985 | 0.146* | 0.50 |
H15E | 0.5015 | 0.3802 | 1.5615 | 0.146* | 0.50 |
H15F | 0.5086 | 0.4191 | 1.4753 | 0.146* | 0.50 |
C33 | 0.31242 (13) | −0.1167 (2) | 1.0136 (3) | 0.1222 (15) | |
H33A | 0.3272 | −0.1244 | 0.9694 | 0.183* | 0.50 |
H33B | 0.3284 | −0.1591 | 1.0651 | 0.183* | 0.50 |
H33C | 0.3216 | −0.0598 | 1.0418 | 0.183* | 0.50 |
H33D | 0.3243 | −0.1045 | 1.0814 | 0.183* | 0.50 |
H33E | 0.3230 | −0.0698 | 0.9858 | 0.183* | 0.50 |
H33F | 0.3299 | −0.1691 | 1.0091 | 0.183* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N3 | 0.0521 (16) | 0.0615 (17) | 0.0859 (19) | −0.0059 (14) | 0.0323 (15) | −0.0099 (16) |
C23 | 0.0393 (16) | 0.0526 (19) | 0.0556 (19) | 0.0082 (16) | 0.0227 (15) | −0.0020 (18) |
S1 | 0.0519 (5) | 0.1001 (7) | 0.0479 (5) | −0.0069 (5) | 0.0227 (4) | 0.0175 (5) |
S2 | 0.0480 (5) | 0.0929 (6) | 0.0759 (5) | 0.0128 (5) | 0.0376 (4) | 0.0274 (5) |
S3 | 0.0803 (6) | 0.0506 (5) | 0.0908 (7) | 0.0126 (5) | 0.0149 (5) | −0.0055 (5) |
C5 | 0.0419 (17) | 0.0466 (17) | 0.0449 (17) | 0.0007 (14) | 0.0236 (15) | 0.0008 (14) |
C4 | 0.0376 (16) | 0.0532 (18) | 0.0442 (17) | 0.0039 (13) | 0.0135 (14) | 0.0026 (14) |
C8 | 0.0377 (16) | 0.0436 (17) | 0.0478 (17) | 0.0024 (13) | 0.0244 (15) | 0.0019 (14) |
C3 | 0.0461 (17) | 0.0451 (17) | 0.0389 (16) | 0.0040 (14) | 0.0213 (15) | 0.0027 (14) |
C9 | 0.0473 (17) | 0.0571 (19) | 0.0341 (16) | −0.0029 (17) | 0.0179 (14) | 0.0039 (16) |
C6 | 0.0392 (16) | 0.0489 (17) | 0.0346 (14) | 0.0000 (14) | 0.0158 (14) | 0.0036 (13) |
C25 | 0.0463 (16) | 0.0522 (19) | 0.0524 (18) | 0.0053 (17) | 0.0184 (15) | −0.0036 (16) |
C12 | 0.0491 (19) | 0.076 (2) | 0.0425 (18) | −0.001 (2) | 0.0192 (16) | −0.0053 (18) |
C24 | 0.0472 (15) | 0.0413 (16) | 0.0455 (18) | −0.0012 (13) | 0.0229 (16) | −0.0031 (15) |
C7 | 0.0366 (15) | 0.0571 (18) | 0.0442 (17) | 0.0053 (14) | 0.0167 (13) | 0.0094 (15) |
C1 | 0.0528 (19) | 0.056 (2) | 0.0499 (18) | 0.0073 (16) | 0.0251 (17) | 0.0084 (15) |
C28 | 0.069 (2) | 0.090 (2) | 0.056 (2) | 0.007 (2) | 0.0378 (19) | 0.0080 (19) |
C14 | 0.062 (2) | 0.0520 (19) | 0.0457 (18) | 0.0010 (17) | 0.0250 (17) | 0.0021 (16) |
C27 | 0.065 (2) | 0.0493 (18) | 0.055 (2) | 0.0148 (16) | 0.0259 (17) | 0.0006 (16) |
C19 | 0.056 (2) | 0.071 (2) | 0.055 (2) | 0.0114 (19) | 0.0383 (18) | 0.0034 (19) |
C20 | 0.0417 (19) | 0.080 (2) | 0.056 (2) | −0.0005 (19) | 0.0179 (17) | −0.0137 (19) |
C18 | 0.073 (2) | 0.0468 (18) | 0.067 (2) | −0.0048 (19) | 0.041 (2) | −0.0080 (18) |
C13 | 0.055 (2) | 0.070 (2) | 0.0505 (19) | 0.0155 (18) | 0.0189 (18) | 0.0120 (18) |
N2 | 0.091 (2) | 0.086 (2) | 0.0539 (17) | 0.0120 (15) | 0.0361 (16) | 0.0162 (15) |
C16 | 0.0381 (17) | 0.0518 (19) | 0.0558 (19) | 0.0007 (15) | 0.0296 (16) | −0.0028 (16) |
C17 | 0.0477 (19) | 0.075 (2) | 0.0528 (18) | −0.0146 (18) | 0.0247 (16) | −0.0135 (19) |
C11 | 0.070 (2) | 0.054 (2) | 0.066 (2) | −0.0078 (19) | 0.032 (2) | −0.0105 (18) |
C2 | 0.0510 (18) | 0.0495 (19) | 0.051 (2) | 0.0041 (15) | 0.0238 (17) | 0.0023 (16) |
C26 | 0.0671 (18) | 0.0438 (16) | 0.0445 (18) | 0.0073 (14) | 0.0208 (17) | −0.0035 (15) |
N1 | 0.0729 (18) | 0.096 (2) | 0.104 (2) | 0.0063 (16) | 0.0622 (18) | 0.0210 (17) |
C10 | 0.056 (2) | 0.056 (2) | 0.0568 (19) | 0.0113 (17) | 0.0235 (17) | 0.0077 (17) |
C21 | 0.0519 (19) | 0.0524 (19) | 0.068 (2) | −0.0064 (17) | 0.0334 (18) | −0.0156 (17) |
C32 | 0.121 (3) | 0.089 (3) | 0.062 (2) | 0.026 (3) | 0.055 (2) | −0.002 (2) |
C31 | 0.116 (3) | 0.087 (3) | 0.129 (4) | 0.009 (3) | 0.099 (3) | −0.005 (3) |
C29 | 0.068 (2) | 0.081 (2) | 0.061 (2) | −0.0042 (18) | 0.030 (2) | 0.0018 (17) |
C30 | 0.079 (2) | 0.0382 (18) | 0.113 (3) | 0.0066 (17) | 0.059 (3) | −0.002 (2) |
C22 | 0.077 (2) | 0.110 (3) | 0.075 (2) | 0.033 (2) | 0.040 (2) | 0.023 (2) |
C15 | 0.063 (2) | 0.126 (3) | 0.077 (2) | −0.007 (2) | 0.013 (2) | −0.017 (2) |
C33 | 0.078 (3) | 0.080 (3) | 0.222 (5) | −0.013 (2) | 0.083 (3) | −0.034 (3) |
Geometric parameters (Å, º) top
N3—C23 | 1.139 (3) | C20—H20 | 0.9300 |
C23—C24 | 1.442 (3) | C18—C17 | 1.389 (3) |
S1—C6 | 1.756 (2) | C18—H18 | 0.9300 |
S1—C9 | 1.774 (3) | C13—H13 | 0.9300 |
S2—C5 | 1.766 (2) | N2—C2 | 1.138 (3) |
S2—C16 | 1.773 (3) | C16—C17 | 1.367 (3) |
S3—C26 | 1.754 (2) | C16—C21 | 1.376 (3) |
S3—C27 | 1.772 (3) | C17—H17 | 0.9300 |
C5—C4 | 1.382 (3) | C11—C10 | 1.377 (3) |
C5—C6 | 1.399 (3) | C11—H11 | 0.9300 |
C4—C3 | 1.383 (3) | C26—C26i | 1.418 (5) |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
C8—C7 | 1.379 (3) | C21—H21 | 0.9300 |
C8—C3 | 1.399 (3) | C32—C31 | 1.374 (4) |
C8—C1 | 1.443 (3) | C32—H32 | 0.9300 |
C3—C2 | 1.435 (3) | C31—C30 | 1.366 (4) |
C9—C14 | 1.376 (3) | C31—H31 | 0.9300 |
C9—C10 | 1.380 (3) | C29—C30 | 1.369 (4) |
C6—C7 | 1.389 (3) | C29—H29 | 0.9300 |
C25—C24 | 1.381 (3) | C30—C33 | 1.511 (4) |
C25—C26 | 1.382 (3) | C22—H22A | 0.9600 |
C25—H25 | 0.9300 | C22—H22B | 0.9600 |
C12—C13 | 1.369 (3) | C22—H22C | 0.9600 |
C12—C11 | 1.384 (3) | C22—H22D | 0.9600 |
C12—C15 | 1.511 (4) | C22—H22E | 0.9600 |
C24—C24i | 1.394 (4) | C22—H22F | 0.9600 |
C7—H7 | 0.9300 | C15—H15A | 0.9600 |
C1—N1 | 1.131 (3) | C15—H15B | 0.9600 |
C28—C27 | 1.362 (3) | C15—H15C | 0.9600 |
C28—C29 | 1.378 (4) | C15—H15D | 0.9600 |
C28—H28 | 0.9300 | C15—H15E | 0.9600 |
C14—C13 | 1.376 (3) | C15—H15F | 0.9600 |
C14—H14 | 0.9300 | C33—H33A | 0.9600 |
C27—C32 | 1.377 (4) | C33—H33B | 0.9600 |
C19—C20 | 1.363 (3) | C33—H33C | 0.9600 |
C19—C18 | 1.378 (3) | C33—H33D | 0.9600 |
C19—C22 | 1.510 (3) | C33—H33E | 0.9600 |
C20—C21 | 1.375 (3) | C33—H33F | 0.9600 |
| | | |
N3—C23—C24 | 179.0 (3) | C31—C32—C27 | 119.2 (3) |
C6—S1—C9 | 103.18 (11) | C31—C32—H32 | 120.4 |
C5—S2—C16 | 102.86 (12) | C27—C32—H32 | 120.4 |
C26—S3—C27 | 103.23 (13) | C30—C31—C32 | 122.3 (3) |
C4—C5—C6 | 119.5 (2) | C30—C31—H31 | 118.8 |
C4—C5—S2 | 122.5 (2) | C32—C31—H31 | 118.8 |
C6—C5—S2 | 117.97 (18) | C30—C29—C28 | 121.4 (3) |
C5—C4—C3 | 121.2 (2) | C30—C29—H29 | 119.3 |
C5—C4—H4 | 119.4 | C28—C29—H29 | 119.3 |
C3—C4—H4 | 119.4 | C31—C30—C29 | 117.4 (3) |
C7—C8—C3 | 119.5 (2) | C31—C30—C33 | 121.5 (3) |
C7—C8—C1 | 120.4 (2) | C29—C30—C33 | 121.1 (4) |
C3—C8—C1 | 120.1 (2) | C19—C22—H22A | 109.5 |
C4—C3—C8 | 119.3 (2) | C19—C22—H22B | 109.5 |
C4—C3—C2 | 120.7 (2) | H22A—C22—H22B | 109.5 |
C8—C3—C2 | 120.0 (2) | C19—C22—H22C | 109.5 |
C14—C9—C10 | 119.5 (2) | H22A—C22—H22C | 109.5 |
C14—C9—S1 | 119.5 (2) | H22B—C22—H22C | 109.5 |
C10—C9—S1 | 120.8 (2) | C19—C22—H22D | 109.5 |
C7—C6—C5 | 119.1 (2) | H22A—C22—H22D | 141.1 |
C7—C6—S1 | 122.40 (19) | H22B—C22—H22D | 56.3 |
C5—C6—S1 | 118.43 (17) | H22C—C22—H22D | 56.3 |
C24—C25—C26 | 121.0 (2) | C19—C22—H22E | 109.5 |
C24—C25—H25 | 119.5 | H22A—C22—H22E | 56.3 |
C26—C25—H25 | 119.5 | H22B—C22—H22E | 141.1 |
C13—C12—C11 | 117.3 (3) | H22C—C22—H22E | 56.3 |
C13—C12—C15 | 121.1 (3) | H22D—C22—H22E | 109.5 |
C11—C12—C15 | 121.6 (3) | C19—C22—H22F | 109.5 |
C25—C24—C24i | 119.78 (14) | H22A—C22—H22F | 56.3 |
C25—C24—C23 | 120.8 (2) | H22B—C22—H22F | 56.3 |
C24i—C24—C23 | 119.44 (13) | H22C—C22—H22F | 141.1 |
C8—C7—C6 | 121.2 (2) | H22D—C22—H22F | 109.5 |
C8—C7—H7 | 119.4 | H22E—C22—H22F | 109.5 |
C6—C7—H7 | 119.4 | C12—C15—H15A | 109.5 |
N1—C1—C8 | 179.8 (3) | C12—C15—H15B | 109.5 |
C27—C28—C29 | 120.3 (3) | H15A—C15—H15B | 109.5 |
C27—C28—H28 | 119.9 | C12—C15—H15C | 109.5 |
C29—C28—H28 | 119.9 | H15A—C15—H15C | 109.5 |
C13—C14—C9 | 119.7 (3) | H15B—C15—H15C | 109.5 |
C13—C14—H14 | 120.1 | C12—C15—H15D | 109.5 |
C9—C14—H14 | 120.1 | H15A—C15—H15D | 141.1 |
C28—C27—C32 | 119.3 (3) | H15B—C15—H15D | 56.3 |
C28—C27—S3 | 119.7 (2) | H15C—C15—H15D | 56.3 |
C32—C27—S3 | 120.8 (3) | C12—C15—H15E | 109.5 |
C20—C19—C18 | 117.5 (3) | H15A—C15—H15E | 56.3 |
C20—C19—C22 | 121.7 (3) | H15B—C15—H15E | 141.1 |
C18—C19—C22 | 120.8 (3) | H15C—C15—H15E | 56.3 |
C19—C20—C21 | 122.4 (3) | H15D—C15—H15E | 109.5 |
C19—C20—H20 | 118.8 | C12—C15—H15F | 109.5 |
C21—C20—H20 | 118.8 | H15A—C15—H15F | 56.3 |
C19—C18—C17 | 121.0 (3) | H15B—C15—H15F | 56.3 |
C19—C18—H18 | 119.5 | H15C—C15—H15F | 141.1 |
C17—C18—H18 | 119.5 | H15D—C15—H15F | 109.5 |
C12—C13—C14 | 122.1 (3) | H15E—C15—H15F | 109.5 |
C12—C13—H13 | 119.0 | C30—C33—H33A | 109.5 |
C14—C13—H13 | 119.0 | C30—C33—H33B | 109.5 |
C17—C16—C21 | 118.9 (3) | H33A—C33—H33B | 109.5 |
C17—C16—S2 | 120.2 (2) | C30—C33—H33C | 109.5 |
C21—C16—S2 | 120.8 (2) | H33A—C33—H33C | 109.5 |
C16—C17—C18 | 120.4 (3) | H33B—C33—H33C | 109.5 |
C16—C17—H17 | 119.8 | C30—C33—H33D | 109.5 |
C18—C17—H17 | 119.8 | H33A—C33—H33D | 141.1 |
C10—C11—C12 | 121.8 (3) | H33B—C33—H33D | 56.3 |
C10—C11—H11 | 119.1 | H33C—C33—H33D | 56.3 |
C12—C11—H11 | 119.1 | C30—C33—H33E | 109.5 |
N2—C2—C3 | 179.2 (3) | H33A—C33—H33E | 56.3 |
C25—C26—C26i | 119.18 (14) | H33B—C33—H33E | 141.1 |
C25—C26—S3 | 124.00 (19) | H33C—C33—H33E | 56.3 |
C26i—C26—S3 | 116.81 (9) | H33D—C33—H33E | 109.5 |
C11—C10—C9 | 119.5 (3) | C30—C33—H33F | 109.5 |
C11—C10—H10 | 120.2 | H33A—C33—H33F | 56.3 |
C9—C10—H10 | 120.2 | H33B—C33—H33F | 56.3 |
C20—C21—C16 | 119.8 (3) | H33C—C33—H33F | 141.1 |
C20—C21—H21 | 120.1 | H33D—C33—H33F | 109.5 |
C16—C21—H21 | 120.1 | H33E—C33—H33F | 109.5 |
| | | |
C16—S2—C5—C4 | −24.6 (2) | C22—C19—C20—C21 | 178.3 (2) |
C16—S2—C5—C6 | 156.5 (2) | C20—C19—C18—C17 | 0.0 (4) |
C6—C5—C4—C3 | −0.9 (4) | C22—C19—C18—C17 | −179.7 (2) |
S2—C5—C4—C3 | −179.82 (19) | C11—C12—C13—C14 | 0.2 (4) |
C5—C4—C3—C8 | 2.0 (4) | C15—C12—C13—C14 | −179.6 (2) |
C5—C4—C3—C2 | −177.2 (2) | C9—C14—C13—C12 | −0.3 (4) |
C7—C8—C3—C4 | −0.7 (4) | C5—S2—C16—C17 | −75.0 (2) |
C1—C8—C3—C4 | 179.6 (2) | C5—S2—C16—C21 | 108.4 (2) |
C7—C8—C3—C2 | 178.5 (2) | C21—C16—C17—C18 | −2.3 (4) |
C1—C8—C3—C2 | −1.2 (4) | S2—C16—C17—C18 | −178.92 (19) |
C6—S1—C9—C14 | −117.35 (19) | C19—C18—C17—C16 | 1.9 (4) |
C6—S1—C9—C10 | 67.1 (2) | C13—C12—C11—C10 | 0.6 (4) |
C4—C5—C6—C7 | −1.4 (4) | C15—C12—C11—C10 | −179.6 (2) |
S2—C5—C6—C7 | 177.56 (19) | C24—C25—C26—C26i | −0.5 (4) |
C4—C5—C6—S1 | 180.00 (18) | C24—C25—C26—S3 | 178.7 (2) |
S2—C5—C6—S1 | −1.1 (3) | C27—S3—C26—C25 | 4.3 (3) |
C9—S1—C6—C7 | 20.3 (2) | C27—S3—C26—C26i | −176.6 (3) |
C9—S1—C6—C5 | −161.1 (2) | C12—C11—C10—C9 | −1.2 (4) |
C26—C25—C24—C24i | −0.2 (4) | C14—C9—C10—C11 | 1.1 (4) |
C26—C25—C24—C23 | −179.8 (2) | S1—C9—C10—C11 | 176.65 (19) |
C3—C8—C7—C6 | −1.6 (4) | C19—C20—C21—C16 | 1.1 (4) |
C1—C8—C7—C6 | 178.1 (2) | C17—C16—C21—C20 | 0.8 (4) |
C5—C6—C7—C8 | 2.7 (4) | S2—C16—C21—C20 | 177.48 (19) |
S1—C6—C7—C8 | −178.76 (19) | C28—C27—C32—C31 | −0.1 (5) |
C10—C9—C14—C13 | −0.3 (4) | S3—C27—C32—C31 | −175.0 (3) |
S1—C9—C14—C13 | −175.95 (19) | C27—C32—C31—C30 | 1.5 (5) |
C29—C28—C27—C32 | −0.7 (5) | C27—C28—C29—C30 | 0.1 (5) |
C29—C28—C27—S3 | 174.3 (2) | C32—C31—C30—C29 | −2.1 (5) |
C26—S3—C27—C28 | 88.1 (3) | C32—C31—C30—C33 | 176.5 (3) |
C26—S3—C27—C32 | −97.0 (3) | C28—C29—C30—C31 | 1.2 (5) |
C18—C19—C20—C21 | −1.5 (4) | C28—C29—C30—C33 | −177.4 (3) |
Symmetry code: (i) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···N3ii | 0.93 | 2.62 | 3.491 (3) | 156 |
C28—H28···Cg2iii | 0.93 | 2.63 | 3.519 (4) | 161 |
Symmetry codes: (ii) −x+1/2, −y+1/2, −z+2; (iii) −x+1/2, −y+1/2, −z+1. |