Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617003035/yf3115sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617003035/yf3115Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617003035/yf3115Iasup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617003035/yf3115Isup4.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617003035/yf3115sup5.pdf | |
Text file https://doi.org/10.1107/S2053229617003035/yf3115sup6.txt |
CCDC references: 1534363; 1534362
For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C30H18N4S | Z = 1 |
Mr = 466.54 | F(000) = 242 |
Triclinic, P1 | Dx = 1.362 Mg m−3 |
a = 8.3617 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.7261 (8) Å | Cell parameters from 6909 reflections |
c = 8.8590 (8) Å | θ = 2.4–32.1° |
α = 104.451 (1)° | µ = 0.17 mm−1 |
β = 94.187 (1)° | T = 215 K |
γ = 112.344 (1)° | Prism, yellow |
V = 568.69 (9) Å3 | 0.4 × 0.3 × 0.2 mm |
Bruker APEXII CCD diffractometer | 6746 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.018 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 32.1°, θmin = 2.4° |
Tmin = 0.673, Tmax = 0.746 | h = −12→12 |
9318 measured reflections | k = −12→12 |
7051 independent reflections | l = −13→12 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0711P)2 + 0.0117P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.097 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.23 e Å−3 |
7051 reflections | Δρmin = −0.32 e Å−3 |
388 parameters | Absolute structure: Flack x determined using 3101 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
3 restraints | Absolute structure parameter: 0.038 (17) |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.49611 (6) | 0.80527 (6) | 0.74131 (5) | 0.04375 (13) | |
C1 | 0.4137 (2) | 0.5379 (2) | 0.53948 (18) | 0.0282 (3) | |
N1 | 0.3503 (2) | 0.6086 (2) | 0.66070 (19) | 0.0381 (3) | |
C2 | 0.5826 (2) | 0.6541 (2) | 0.52381 (19) | 0.0277 (3) | |
N2 | 0.6439 (2) | 0.8122 (2) | 0.6326 (2) | 0.0377 (3) | |
N3 | 0.3303 (2) | 0.15250 (17) | 0.20087 (16) | 0.0283 (3) | |
C3 | 0.6718 (2) | 0.5973 (2) | 0.4072 (2) | 0.0286 (3) | |
H3 | 0.785 (4) | 0.664 (4) | 0.401 (3) | 0.042 (7)* | |
N4 | 0.6788 (2) | 0.36446 (18) | 0.19717 (16) | 0.0282 (3) | |
C4 | 0.5900 (2) | 0.43122 (18) | 0.30775 (17) | 0.0247 (3) | |
C5 | 0.4134 (2) | 0.31763 (18) | 0.31611 (17) | 0.0250 (3) | |
C6 | 0.3278 (2) | 0.3680 (2) | 0.43058 (19) | 0.0291 (3) | |
H6 | 0.211 (4) | 0.290 (4) | 0.436 (3) | 0.041 (7)* | |
C7 | 0.2784 (2) | 0.1259 (2) | 0.03953 (18) | 0.0275 (3) | |
C8 | 0.2783 (2) | 0.2470 (2) | −0.0369 (2) | 0.0345 (3) | |
H8 | 0.321 (4) | 0.375 (4) | 0.027 (3) | 0.047 (7)* | |
C9 | 0.2071 (3) | 0.1843 (3) | −0.1981 (2) | 0.0418 (4) | |
H9 | 0.202 (4) | 0.269 (4) | −0.253 (4) | 0.049 (8)* | |
C10 | 0.1359 (3) | 0.0071 (3) | −0.2787 (2) | 0.0435 (4) | |
H10 | 0.069 (5) | −0.045 (5) | −0.399 (4) | 0.060 (9)* | |
C11 | 0.1353 (2) | −0.1134 (3) | −0.2020 (2) | 0.0368 (4) | |
H11 | 0.082 (4) | −0.240 (4) | −0.262 (3) | 0.042 (7)* | |
C12 | 0.2081 (2) | −0.0541 (2) | −0.03998 (18) | 0.0288 (3) | |
C13 | 0.2171 (2) | −0.1396 (2) | 0.0787 (2) | 0.0288 (3) | |
C14 | 0.1645 (3) | −0.3138 (2) | 0.0737 (3) | 0.0412 (4) | |
H14 | 0.118 (5) | −0.408 (5) | −0.025 (4) | 0.055 (8)* | |
C15 | 0.1799 (3) | −0.3528 (3) | 0.2143 (3) | 0.0488 (5) | |
H15 | 0.128 (5) | −0.475 (5) | 0.217 (4) | 0.055 (8)* | |
C16 | 0.2484 (3) | −0.2215 (3) | 0.3593 (3) | 0.0442 (4) | |
H16 | 0.254 (5) | −0.250 (5) | 0.458 (4) | 0.057 (8)* | |
C17 | 0.3061 (3) | −0.0466 (2) | 0.3683 (2) | 0.0350 (3) | |
H17 | 0.352 (4) | 0.048 (4) | 0.481 (3) | 0.038 (6)* | |
C18 | 0.2894 (2) | −0.00871 (19) | 0.22618 (19) | 0.0274 (3) | |
C19 | 0.7079 (2) | 0.3993 (2) | 0.05368 (18) | 0.0272 (3) | |
C20 | 0.6842 (2) | 0.5257 (2) | −0.0026 (2) | 0.0342 (3) | |
H20 | 0.648 (4) | 0.610 (4) | 0.064 (4) | 0.043 (7)* | |
C21 | 0.7262 (3) | 0.5344 (3) | −0.1496 (2) | 0.0422 (4) | |
H21 | 0.721 (5) | 0.626 (5) | −0.193 (4) | 0.059 (9)* | |
C22 | 0.7865 (3) | 0.4180 (3) | −0.2394 (2) | 0.0447 (5) | |
H22 | 0.813 (4) | 0.442 (5) | −0.341 (4) | 0.055 (8)* | |
C23 | 0.8104 (3) | 0.2922 (3) | −0.1825 (2) | 0.0384 (4) | |
H23 | 0.850 (4) | 0.216 (4) | −0.242 (4) | 0.056 (8)* | |
C24 | 0.7734 (2) | 0.2838 (2) | −0.03248 (19) | 0.0286 (3) | |
C25 | 0.7896 (2) | 0.17885 (19) | 0.06540 (19) | 0.0275 (3) | |
C26 | 0.8553 (2) | 0.0510 (2) | 0.0500 (2) | 0.0345 (3) | |
H26 | 0.897 (4) | 0.008 (4) | −0.050 (4) | 0.050 (8)* | |
C27 | 0.8594 (3) | −0.0192 (2) | 0.1735 (3) | 0.0402 (4) | |
H27 | 0.910 (4) | −0.105 (4) | 0.167 (4) | 0.052 (8)* | |
C28 | 0.7977 (3) | 0.0342 (3) | 0.3117 (3) | 0.0403 (4) | |
H28 | 0.797 (4) | −0.017 (4) | 0.397 (4) | 0.043 (7)* | |
C29 | 0.7311 (3) | 0.1601 (2) | 0.3295 (2) | 0.0341 (3) | |
H29 | 0.697 (5) | 0.206 (5) | 0.421 (4) | 0.058 (9)* | |
C30 | 0.7290 (2) | 0.23084 (19) | 0.20523 (19) | 0.0275 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0424 (2) | 0.0442 (2) | 0.0356 (2) | 0.02533 (19) | 0.00061 (17) | −0.01320 (17) |
C1 | 0.0324 (7) | 0.0303 (7) | 0.0242 (6) | 0.0185 (6) | 0.0053 (5) | 0.0031 (5) |
N1 | 0.0405 (8) | 0.0427 (8) | 0.0306 (7) | 0.0241 (7) | 0.0077 (6) | −0.0015 (6) |
C2 | 0.0323 (7) | 0.0235 (6) | 0.0276 (6) | 0.0160 (5) | 0.0023 (5) | 0.0018 (5) |
N2 | 0.0380 (7) | 0.0297 (7) | 0.0385 (7) | 0.0184 (6) | 0.0001 (6) | −0.0064 (6) |
N3 | 0.0369 (7) | 0.0205 (5) | 0.0241 (5) | 0.0106 (5) | 0.0050 (5) | 0.0027 (4) |
C3 | 0.0315 (7) | 0.0223 (6) | 0.0317 (7) | 0.0128 (5) | 0.0076 (6) | 0.0043 (5) |
N4 | 0.0385 (7) | 0.0251 (6) | 0.0283 (6) | 0.0193 (5) | 0.0142 (5) | 0.0085 (5) |
C4 | 0.0318 (7) | 0.0210 (6) | 0.0247 (6) | 0.0143 (5) | 0.0086 (5) | 0.0059 (5) |
C5 | 0.0307 (7) | 0.0204 (6) | 0.0239 (6) | 0.0121 (5) | 0.0054 (5) | 0.0037 (5) |
C6 | 0.0314 (7) | 0.0267 (7) | 0.0283 (7) | 0.0129 (6) | 0.0084 (6) | 0.0047 (5) |
C7 | 0.0269 (6) | 0.0290 (7) | 0.0245 (6) | 0.0112 (5) | 0.0068 (5) | 0.0046 (5) |
C8 | 0.0344 (8) | 0.0363 (8) | 0.0316 (7) | 0.0115 (7) | 0.0070 (6) | 0.0129 (6) |
C9 | 0.0366 (9) | 0.0571 (12) | 0.0326 (8) | 0.0156 (8) | 0.0090 (7) | 0.0203 (8) |
C10 | 0.0362 (9) | 0.0620 (13) | 0.0264 (7) | 0.0168 (8) | 0.0063 (6) | 0.0086 (8) |
C11 | 0.0309 (8) | 0.0429 (9) | 0.0273 (7) | 0.0140 (7) | 0.0045 (6) | −0.0028 (7) |
C12 | 0.0257 (6) | 0.0308 (7) | 0.0258 (6) | 0.0128 (6) | 0.0049 (5) | −0.0003 (5) |
C13 | 0.0269 (6) | 0.0237 (6) | 0.0326 (7) | 0.0129 (5) | 0.0027 (5) | −0.0002 (5) |
C14 | 0.0430 (9) | 0.0228 (7) | 0.0504 (10) | 0.0149 (7) | −0.0034 (8) | −0.0005 (7) |
C15 | 0.0553 (12) | 0.0258 (8) | 0.0621 (13) | 0.0170 (8) | −0.0019 (10) | 0.0110 (8) |
C16 | 0.0523 (11) | 0.0348 (9) | 0.0484 (11) | 0.0197 (8) | 0.0031 (9) | 0.0167 (8) |
C17 | 0.0414 (9) | 0.0303 (7) | 0.0333 (8) | 0.0156 (7) | 0.0044 (7) | 0.0092 (6) |
C18 | 0.0304 (7) | 0.0216 (6) | 0.0296 (7) | 0.0124 (5) | 0.0049 (5) | 0.0040 (5) |
C19 | 0.0296 (7) | 0.0252 (6) | 0.0255 (6) | 0.0106 (5) | 0.0075 (5) | 0.0060 (5) |
C20 | 0.0367 (8) | 0.0315 (7) | 0.0359 (8) | 0.0140 (6) | 0.0071 (6) | 0.0126 (6) |
C21 | 0.0441 (10) | 0.0448 (10) | 0.0351 (9) | 0.0123 (8) | 0.0039 (7) | 0.0183 (8) |
C22 | 0.0502 (11) | 0.0477 (11) | 0.0257 (8) | 0.0099 (9) | 0.0070 (7) | 0.0096 (7) |
C23 | 0.0402 (9) | 0.0379 (9) | 0.0262 (7) | 0.0096 (7) | 0.0098 (6) | 0.0005 (6) |
C24 | 0.0280 (7) | 0.0250 (6) | 0.0263 (6) | 0.0076 (5) | 0.0071 (5) | 0.0014 (5) |
C25 | 0.0254 (6) | 0.0217 (6) | 0.0310 (7) | 0.0090 (5) | 0.0079 (5) | 0.0009 (5) |
C26 | 0.0276 (7) | 0.0246 (7) | 0.0470 (9) | 0.0119 (6) | 0.0111 (6) | 0.0004 (6) |
C27 | 0.0331 (8) | 0.0281 (7) | 0.0629 (12) | 0.0175 (6) | 0.0109 (8) | 0.0110 (8) |
C28 | 0.0396 (9) | 0.0335 (8) | 0.0567 (11) | 0.0203 (7) | 0.0122 (8) | 0.0195 (8) |
C29 | 0.0407 (8) | 0.0314 (7) | 0.0379 (8) | 0.0202 (7) | 0.0133 (7) | 0.0132 (6) |
C30 | 0.0310 (7) | 0.0217 (6) | 0.0311 (7) | 0.0134 (5) | 0.0094 (6) | 0.0050 (5) |
S1—N2 | 1.6137 (19) | C11—C12 | 1.400 (2) |
S1—N1 | 1.6161 (19) | C12—C13 | 1.446 (2) |
C1—N1 | 1.347 (2) | C13—C14 | 1.400 (2) |
C1—C6 | 1.421 (2) | C13—C18 | 1.411 (2) |
C1—C2 | 1.433 (2) | C14—C15 | 1.381 (3) |
C2—N2 | 1.350 (2) | C15—C16 | 1.397 (3) |
C2—C3 | 1.417 (2) | C16—C17 | 1.394 (3) |
N3—C18 | 1.3960 (19) | C17—C18 | 1.390 (2) |
N3—C7 | 1.397 (2) | C19—C20 | 1.389 (2) |
N3—C5 | 1.4150 (19) | C19—C24 | 1.412 (2) |
C3—C4 | 1.366 (2) | C20—C21 | 1.386 (3) |
N4—C19 | 1.396 (2) | C21—C22 | 1.401 (3) |
N4—C30 | 1.3962 (19) | C22—C23 | 1.389 (3) |
N4—C4 | 1.4147 (18) | C23—C24 | 1.400 (2) |
C4—C5 | 1.452 (2) | C24—C25 | 1.443 (2) |
C5—C6 | 1.363 (2) | C25—C26 | 1.402 (2) |
C7—C8 | 1.389 (2) | C25—C30 | 1.408 (2) |
C7—C12 | 1.412 (2) | C26—C27 | 1.384 (3) |
C8—C9 | 1.390 (3) | C27—C28 | 1.404 (3) |
C9—C10 | 1.394 (3) | C28—C29 | 1.390 (2) |
C10—C11 | 1.386 (3) | C29—C30 | 1.392 (2) |
N2—S1—N1 | 101.31 (8) | C7—C12—C13 | 106.97 (13) |
N1—C1—C6 | 126.37 (16) | C14—C13—C18 | 119.34 (17) |
N1—C1—C2 | 113.35 (15) | C14—C13—C12 | 133.66 (16) |
C6—C1—C2 | 120.26 (14) | C18—C13—C12 | 106.94 (13) |
C1—N1—S1 | 106.05 (13) | C15—C14—C13 | 118.82 (18) |
N2—C2—C3 | 126.24 (16) | C14—C15—C16 | 120.92 (18) |
N2—C2—C1 | 113.16 (15) | C17—C16—C15 | 121.75 (19) |
C3—C2—C1 | 120.55 (14) | C18—C17—C16 | 116.88 (17) |
C2—N2—S1 | 106.11 (13) | C17—C18—N3 | 128.99 (15) |
C18—N3—C7 | 108.70 (13) | C17—C18—C13 | 122.27 (15) |
C18—N3—C5 | 126.86 (13) | N3—C18—C13 | 108.70 (14) |
C7—N3—C5 | 124.43 (13) | C20—C19—N4 | 128.98 (15) |
C4—C3—C2 | 118.17 (14) | C20—C19—C24 | 122.38 (15) |
C19—N4—C30 | 108.60 (12) | N4—C19—C24 | 108.62 (14) |
C19—N4—C4 | 127.14 (13) | C21—C20—C19 | 117.33 (18) |
C30—N4—C4 | 123.65 (13) | C20—C21—C22 | 121.35 (19) |
C3—C4—N4 | 120.24 (14) | C23—C22—C21 | 121.12 (17) |
C3—C4—C5 | 121.23 (13) | C22—C23—C24 | 118.58 (18) |
N4—C4—C5 | 118.50 (13) | C23—C24—C19 | 119.20 (17) |
C6—C5—N3 | 120.27 (14) | C23—C24—C25 | 133.84 (17) |
C6—C5—C4 | 121.36 (13) | C19—C24—C25 | 106.95 (14) |
N3—C5—C4 | 118.36 (13) | C26—C25—C30 | 119.01 (16) |
C5—C6—C1 | 118.19 (14) | C26—C25—C24 | 133.93 (16) |
C8—C7—N3 | 128.67 (15) | C30—C25—C24 | 107.02 (13) |
C8—C7—C12 | 122.52 (15) | C27—C26—C25 | 118.79 (16) |
N3—C7—C12 | 108.63 (14) | C26—C27—C28 | 121.24 (16) |
C7—C8—C9 | 117.21 (18) | C29—C28—C27 | 121.11 (18) |
C8—C9—C10 | 121.2 (2) | C28—C29—C30 | 117.19 (17) |
C11—C10—C9 | 121.41 (18) | C29—C30—N4 | 128.49 (14) |
C10—C11—C12 | 118.65 (18) | C29—C30—C25 | 122.66 (14) |
C11—C12—C7 | 118.95 (16) | N4—C30—C25 | 108.78 (14) |
C11—C12—C13 | 133.84 (16) | ||
C6—C1—N1—S1 | −177.72 (14) | C18—C13—C14—C15 | 2.0 (3) |
C2—C1—N1—S1 | 0.72 (18) | C12—C13—C14—C15 | −174.7 (2) |
N2—S1—N1—C1 | −0.48 (15) | C13—C14—C15—C16 | −0.7 (4) |
N1—C1—C2—N2 | −0.7 (2) | C14—C15—C16—C17 | −0.9 (4) |
C6—C1—C2—N2 | 177.83 (15) | C15—C16—C17—C18 | 1.1 (3) |
N1—C1—C2—C3 | 176.81 (15) | C16—C17—C18—N3 | 177.63 (18) |
C6—C1—C2—C3 | −4.6 (2) | C16—C17—C18—C13 | 0.2 (3) |
C3—C2—N2—S1 | −177.03 (14) | C7—N3—C18—C17 | −175.24 (17) |
C1—C2—N2—S1 | 0.33 (17) | C5—N3—C18—C17 | 5.8 (3) |
N1—S1—N2—C2 | 0.08 (14) | C7—N3—C18—C13 | 2.43 (18) |
N2—C2—C3—C4 | 179.17 (16) | C5—N3—C18—C13 | −176.51 (15) |
C1—C2—C3—C4 | 2.0 (2) | C14—C13—C18—C17 | −1.8 (3) |
C2—C3—C4—N4 | −175.38 (14) | C12—C13—C18—C17 | 175.70 (16) |
C2—C3—C4—C5 | 2.6 (2) | C14—C13—C18—N3 | −179.70 (16) |
C19—N4—C4—C3 | −77.0 (2) | C12—C13—C18—N3 | −2.16 (17) |
C30—N4—C4—C3 | 112.99 (18) | C30—N4—C19—C20 | −177.15 (17) |
C19—N4—C4—C5 | 104.96 (18) | C4—N4—C19—C20 | 11.6 (3) |
C30—N4—C4—C5 | −65.0 (2) | C30—N4—C19—C24 | 1.39 (18) |
C18—N3—C5—C6 | −68.9 (2) | C4—N4—C19—C24 | −169.82 (15) |
C7—N3—C5—C6 | 112.30 (18) | N4—C19—C20—C21 | 178.93 (18) |
C18—N3—C5—C4 | 111.72 (18) | C24—C19—C20—C21 | 0.6 (3) |
C7—N3—C5—C4 | −67.1 (2) | C19—C20—C21—C22 | 1.3 (3) |
C3—C4—C5—C6 | −4.7 (2) | C20—C21—C22—C23 | −1.6 (3) |
N4—C4—C5—C6 | 173.24 (14) | C21—C22—C23—C24 | −0.2 (3) |
C3—C4—C5—N3 | 174.60 (14) | C22—C23—C24—C19 | 2.0 (3) |
N4—C4—C5—N3 | −7.4 (2) | C22—C23—C24—C25 | −176.78 (18) |
N3—C5—C6—C1 | −177.31 (14) | C20—C19—C24—C23 | −2.2 (2) |
C4—C5—C6—C1 | 2.0 (2) | N4—C19—C24—C23 | 179.10 (15) |
N1—C1—C6—C5 | −179.13 (16) | C20—C19—C24—C25 | 176.82 (16) |
C2—C1—C6—C5 | 2.5 (2) | N4—C19—C24—C25 | −1.84 (17) |
C18—N3—C7—C8 | 173.43 (16) | C23—C24—C25—C26 | 3.2 (3) |
C5—N3—C7—C8 | −7.6 (3) | C19—C24—C25—C26 | −175.67 (17) |
C18—N3—C7—C12 | −1.72 (18) | C23—C24—C25—C30 | −179.54 (18) |
C5—N3—C7—C12 | 177.25 (14) | C19—C24—C25—C30 | 1.59 (17) |
N3—C7—C8—C9 | −175.27 (17) | C30—C25—C26—C27 | −0.4 (2) |
C12—C7—C8—C9 | −0.7 (2) | C24—C25—C26—C27 | 176.59 (17) |
C7—C8—C9—C10 | 1.2 (3) | C25—C26—C27—C28 | 0.6 (3) |
C8—C9—C10—C11 | −0.9 (3) | C26—C27—C28—C29 | −0.3 (3) |
C9—C10—C11—C12 | 0.1 (3) | C27—C28—C29—C30 | −0.3 (3) |
C10—C11—C12—C7 | 0.4 (2) | C28—C29—C30—N4 | −176.04 (18) |
C10—C11—C12—C13 | 173.87 (18) | C28—C29—C30—C25 | 0.5 (3) |
C8—C7—C12—C11 | 0.0 (2) | C19—N4—C30—C29 | 176.53 (17) |
N3—C7—C12—C11 | 175.46 (14) | C4—N4—C30—C29 | −11.9 (3) |
C8—C7—C12—C13 | −175.14 (15) | C19—N4—C30—C25 | −0.37 (18) |
N3—C7—C12—C13 | 0.37 (17) | C4—N4—C30—C25 | 171.21 (15) |
C11—C12—C13—C14 | 4.1 (3) | C26—C25—C30—C29 | −0.1 (2) |
C7—C12—C13—C14 | 178.1 (2) | C24—C25—C30—C29 | −177.88 (15) |
C11—C12—C13—C18 | −172.95 (17) | C26—C25—C30—N4 | 176.98 (14) |
C7—C12—C13—C18 | 1.09 (17) | C24—C25—C30—N4 | −0.76 (18) |
C30H18N4S·0.125H2O | F(000) = 3892 |
Mr = 468.79 | Dx = 1.380 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.338 (3) Å | Cell parameters from 5147 reflections |
b = 12.9466 (12) Å | θ = 2.6–31.7° |
c = 26.799 (3) Å | µ = 0.17 mm−1 |
β = 113.336 (1)° | T = 215 K |
V = 9027.7 (14) Å3 | Prism, yelllow |
Z = 16 | 0.4 × 0.3 × 0.3 mm |
Bruker APEXII CCD diffractometer | 10976 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 30.2°, θmin = 1.6° |
Tmin = 0.681, Tmax = 0.746 | h = −39→39 |
67947 measured reflections | k = −18→18 |
13333 independent reflections | l = −37→37 |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0697P)2 + 5.8924P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
13333 reflections | Δρmax = 0.48 e Å−3 |
780 parameters | Δρmin = −0.53 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.02474 (2) | 1.13995 (3) | 0.19311 (2) | 0.04780 (11) | |
N1 | 0.07218 (5) | 1.05989 (10) | 0.20898 (5) | 0.0421 (3) | |
C1 | 0.05468 (5) | 0.98031 (10) | 0.17401 (5) | 0.0311 (2) | |
C2 | 0.00249 (5) | 0.99161 (10) | 0.13663 (5) | 0.0304 (2) | |
N2 | −0.01920 (5) | 1.08059 (9) | 0.14316 (6) | 0.0414 (3) | |
N3 | 0.08419 (4) | 0.72000 (8) | 0.13943 (4) | 0.0311 (2) | |
C3 | −0.02123 (5) | 0.91522 (10) | 0.09670 (5) | 0.0297 (2) | |
H3 | −0.0563 (6) | 0.9268 (13) | 0.0692 (7) | 0.039 (4)* | |
N4 | −0.01579 (4) | 0.75220 (8) | 0.05592 (4) | 0.0287 (2) | |
C4 | 0.00651 (4) | 0.82911 (9) | 0.09562 (5) | 0.0261 (2) | |
C5 | 0.05845 (5) | 0.81539 (9) | 0.13586 (5) | 0.0266 (2) | |
C6 | 0.08224 (5) | 0.88987 (10) | 0.17338 (5) | 0.0315 (2) | |
H6 | 0.1154 (7) | 0.8784 (14) | 0.1998 (7) | 0.041 (4)* | |
C7 | 0.07087 (6) | 0.63017 (10) | 0.15940 (5) | 0.0362 (3) | |
C8 | 0.02895 (7) | 0.61231 (14) | 0.17233 (6) | 0.0471 (4) | |
H8 | 0.0036 (8) | 0.6608 (16) | 0.1698 (8) | 0.050 (5)* | |
C9 | 0.02562 (9) | 0.51479 (17) | 0.19285 (7) | 0.0657 (6) | |
H9 | −0.0024 (9) | 0.4987 (18) | 0.2021 (9) | 0.065 (6)* | |
C10 | 0.06337 (10) | 0.43952 (15) | 0.20010 (8) | 0.0714 (6) | |
H10 | 0.0604 (9) | 0.374 (2) | 0.2151 (10) | 0.081 (7)* | |
C11 | 0.10453 (9) | 0.45852 (12) | 0.18729 (7) | 0.0627 (5) | |
H11 | 0.1322 (8) | 0.4036 (18) | 0.1939 (9) | 0.067 (6)* | |
C12 | 0.10923 (6) | 0.55511 (10) | 0.16633 (6) | 0.0440 (4) | |
C13 | 0.14680 (6) | 0.60132 (11) | 0.14956 (5) | 0.0410 (3) | |
C14 | 0.19106 (7) | 0.56484 (15) | 0.14338 (7) | 0.0558 (4) | |
H14 | 0.2002 (8) | 0.4977 (18) | 0.1533 (9) | 0.063 (6)* | |
C15 | 0.21774 (7) | 0.63001 (18) | 0.12331 (7) | 0.0607 (4) | |
H15 | 0.2494 (8) | 0.6013 (17) | 0.1197 (8) | 0.060 (6)* | |
C16 | 0.20229 (6) | 0.73171 (17) | 0.11036 (7) | 0.0526 (4) | |
H16 | 0.2240 (9) | 0.7814 (19) | 0.0948 (10) | 0.074 (7)* | |
C17 | 0.15941 (5) | 0.77099 (13) | 0.11663 (6) | 0.0395 (3) | |
H17 | 0.1488 (7) | 0.8435 (15) | 0.1083 (8) | 0.049 (5)* | |
C18 | 0.13128 (5) | 0.70408 (10) | 0.13490 (5) | 0.0333 (3) | |
C19 | −0.06438 (5) | 0.70704 (10) | 0.04218 (5) | 0.0295 (2) | |
C20 | −0.10084 (6) | 0.72293 (12) | 0.06399 (6) | 0.0404 (3) | |
H20 | −0.0951 (7) | 0.7707 (15) | 0.0922 (8) | 0.048 (5)* | |
C21 | −0.14596 (6) | 0.66586 (14) | 0.04224 (7) | 0.0449 (3) | |
H21 | −0.1720 (8) | 0.6772 (15) | 0.0559 (8) | 0.053 (5)* | |
C22 | −0.15450 (6) | 0.59437 (13) | 0.00054 (6) | 0.0429 (3) | |
H22 | −0.1866 (7) | 0.5575 (15) | −0.0140 (8) | 0.052 (5)* | |
C23 | −0.11784 (6) | 0.57771 (11) | −0.02024 (6) | 0.0374 (3) | |
H23 | −0.1231 (7) | 0.5301 (15) | −0.0491 (8) | 0.048 (5)* | |
C24 | −0.07242 (5) | 0.63462 (9) | 0.00040 (5) | 0.0299 (2) | |
C25 | −0.02786 (5) | 0.63715 (9) | −0.01273 (5) | 0.0287 (2) | |
C26 | −0.01474 (6) | 0.58505 (11) | −0.05090 (5) | 0.0365 (3) | |
H26 | −0.0371 (7) | 0.5330 (14) | −0.0733 (7) | 0.042 (4)* | |
C27 | 0.03096 (6) | 0.60930 (12) | −0.05529 (6) | 0.0405 (3) | |
H27 | 0.0413 (7) | 0.5710 (14) | −0.0810 (8) | 0.045 (5)* | |
C28 | 0.06298 (6) | 0.68673 (12) | −0.02298 (6) | 0.0378 (3) | |
H28 | 0.0948 (7) | 0.7012 (13) | −0.0269 (7) | 0.041 (4)* | |
C29 | 0.05034 (5) | 0.74014 (10) | 0.01491 (5) | 0.0313 (2) | |
H29 | 0.0723 (6) | 0.7958 (13) | 0.0363 (7) | 0.037 (4)* | |
C30 | 0.00566 (5) | 0.71175 (9) | 0.02090 (5) | 0.0271 (2) | |
S1' | 0.12959 (2) | 0.94120 (3) | 0.34020 (2) | 0.05936 (13) | |
C1' | 0.19397 (6) | 0.81208 (10) | 0.36909 (6) | 0.0367 (3) | |
N1' | 0.18828 (6) | 0.91323 (10) | 0.37770 (7) | 0.0530 (4) | |
C2' | 0.14841 (5) | 0.76526 (10) | 0.33130 (5) | 0.0334 (3) | |
N2' | 0.10839 (6) | 0.83138 (10) | 0.31138 (6) | 0.0474 (3) | |
N3' | 0.28274 (4) | 0.59027 (8) | 0.40820 (5) | 0.0312 (2) | |
C3' | 0.14836 (5) | 0.65975 (10) | 0.31711 (5) | 0.0308 (2) | |
H3' | 0.1196 (6) | 0.6287 (13) | 0.2912 (7) | 0.037 (4)* | |
N4' | 0.19397 (4) | 0.49886 (8) | 0.32759 (4) | 0.0267 (2) | |
C4' | 0.19256 (4) | 0.60393 (9) | 0.34173 (5) | 0.0259 (2) | |
C5' | 0.23819 (5) | 0.65071 (9) | 0.38170 (5) | 0.0278 (2) | |
C6' | 0.23919 (5) | 0.75324 (10) | 0.39455 (6) | 0.0357 (3) | |
H6' | 0.2699 (7) | 0.7827 (14) | 0.4220 (8) | 0.047 (5)* | |
C7' | 0.28759 (5) | 0.51215 (10) | 0.44604 (5) | 0.0306 (2) | |
C8' | 0.24982 (6) | 0.46758 (11) | 0.45990 (6) | 0.0354 (3) | |
H8' | 0.2139 (7) | 0.4877 (13) | 0.4421 (7) | 0.038 (4)* | |
C9' | 0.26537 (7) | 0.39350 (13) | 0.50067 (6) | 0.0452 (3) | |
H9' | 0.2403 (7) | 0.3650 (15) | 0.5112 (8) | 0.048 (5)* | |
C10' | 0.31704 (7) | 0.36574 (14) | 0.52700 (7) | 0.0512 (4) | |
H10' | 0.3268 (8) | 0.3181 (17) | 0.5552 (9) | 0.060 (6)* | |
C11' | 0.35423 (6) | 0.41026 (13) | 0.51295 (6) | 0.0448 (3) | |
H11' | 0.3905 (7) | 0.3951 (15) | 0.5322 (8) | 0.049 (5)* | |
C12' | 0.33979 (5) | 0.48434 (11) | 0.47178 (5) | 0.0346 (3) | |
C13' | 0.36768 (5) | 0.54754 (11) | 0.44818 (5) | 0.0348 (3) | |
C14' | 0.41944 (5) | 0.55334 (13) | 0.45505 (6) | 0.0429 (3) | |
H14' | 0.4427 (7) | 0.5070 (14) | 0.4800 (7) | 0.043 (5)* | |
C15' | 0.43383 (6) | 0.62632 (14) | 0.42633 (7) | 0.0476 (4) | |
H15' | 0.4705 (8) | 0.6326 (15) | 0.4315 (8) | 0.055 (5)* | |
C16' | 0.39792 (6) | 0.69372 (13) | 0.39072 (7) | 0.0466 (4) | |
H16' | 0.4097 (7) | 0.7461 (15) | 0.3694 (8) | 0.051 (5)* | |
C17' | 0.34634 (6) | 0.68873 (12) | 0.38199 (7) | 0.0408 (3) | |
H17' | 0.3203 (8) | 0.7355 (16) | 0.3556 (9) | 0.058 (6)* | |
C18' | 0.33197 (5) | 0.61444 (10) | 0.41089 (5) | 0.0331 (3) | |
C19' | 0.16127 (4) | 0.42026 (9) | 0.33048 (5) | 0.0260 (2) | |
C20' | 0.12386 (5) | 0.42199 (11) | 0.35195 (6) | 0.0335 (3) | |
H20' | 0.1161 (6) | 0.4830 (14) | 0.3667 (7) | 0.041 (4)* | |
C21' | 0.09773 (6) | 0.33042 (12) | 0.35025 (6) | 0.0397 (3) | |
H21' | 0.0718 (7) | 0.3289 (15) | 0.3649 (8) | 0.050 (5)* | |
C22' | 0.10826 (6) | 0.24021 (11) | 0.32820 (7) | 0.0409 (3) | |
H22' | 0.0891 (7) | 0.1758 (15) | 0.3269 (8) | 0.052 (5)* | |
C23' | 0.14547 (5) | 0.23880 (10) | 0.30703 (6) | 0.0361 (3) | |
H23' | 0.1524 (7) | 0.1775 (15) | 0.2923 (8) | 0.047 (5)* | |
C24' | 0.17225 (5) | 0.32959 (9) | 0.30790 (5) | 0.0274 (2) | |
C25' | 0.21175 (5) | 0.35531 (9) | 0.28895 (5) | 0.0276 (2) | |
C26' | 0.23661 (6) | 0.29958 (12) | 0.26193 (6) | 0.0381 (3) | |
H26' | 0.2286 (7) | 0.2271 (15) | 0.2536 (7) | 0.046 (5)* | |
C27' | 0.27237 (6) | 0.34950 (14) | 0.24738 (6) | 0.0439 (3) | |
H27' | 0.2904 (7) | 0.3093 (15) | 0.2291 (8) | 0.053 (5)* | |
C28' | 0.28374 (6) | 0.45367 (14) | 0.25950 (6) | 0.0415 (3) | |
H28' | 0.3072 (7) | 0.4879 (15) | 0.2475 (8) | 0.047 (5)* | |
C29' | 0.26005 (5) | 0.51054 (11) | 0.28677 (5) | 0.0335 (3) | |
H29' | 0.2672 (7) | 0.5819 (15) | 0.2944 (7) | 0.045 (5)* | |
C30' | 0.22420 (4) | 0.45983 (9) | 0.30147 (5) | 0.0263 (2) | |
O1S | 0.0000 | 0.8921 (5) | 0.2500 | 0.1051 (18) | 0.5 |
H1SA | 0.0225 | 0.8533 | 0.2728 | 0.126* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0519 (2) | 0.03475 (18) | 0.0598 (2) | −0.00234 (15) | 0.02537 (19) | −0.02004 (16) |
N1 | 0.0442 (7) | 0.0349 (6) | 0.0454 (7) | −0.0065 (5) | 0.0158 (5) | −0.0155 (5) |
C1 | 0.0333 (6) | 0.0276 (6) | 0.0329 (6) | −0.0046 (5) | 0.0135 (5) | −0.0072 (5) |
C2 | 0.0318 (6) | 0.0276 (6) | 0.0353 (6) | −0.0006 (4) | 0.0169 (5) | −0.0043 (5) |
N2 | 0.0416 (6) | 0.0341 (6) | 0.0527 (7) | 0.0026 (5) | 0.0231 (6) | −0.0107 (5) |
N3 | 0.0347 (5) | 0.0243 (5) | 0.0316 (5) | 0.0018 (4) | 0.0103 (4) | 0.0008 (4) |
C3 | 0.0267 (5) | 0.0314 (6) | 0.0304 (6) | −0.0002 (4) | 0.0108 (5) | −0.0039 (5) |
N4 | 0.0278 (5) | 0.0300 (5) | 0.0278 (5) | −0.0050 (4) | 0.0104 (4) | −0.0075 (4) |
C4 | 0.0275 (5) | 0.0260 (5) | 0.0250 (5) | −0.0036 (4) | 0.0108 (4) | −0.0038 (4) |
C5 | 0.0281 (5) | 0.0244 (5) | 0.0267 (5) | −0.0002 (4) | 0.0102 (4) | −0.0010 (4) |
C6 | 0.0282 (6) | 0.0305 (6) | 0.0311 (6) | −0.0014 (5) | 0.0069 (5) | −0.0045 (5) |
C7 | 0.0468 (7) | 0.0265 (6) | 0.0246 (5) | −0.0054 (5) | 0.0026 (5) | 0.0005 (4) |
C8 | 0.0562 (9) | 0.0442 (8) | 0.0336 (7) | −0.0152 (7) | 0.0100 (6) | 0.0025 (6) |
C9 | 0.0814 (14) | 0.0631 (12) | 0.0373 (8) | −0.0371 (11) | 0.0071 (8) | 0.0083 (8) |
C10 | 0.1002 (14) | 0.0388 (9) | 0.0417 (9) | −0.0239 (10) | −0.0076 (9) | 0.0138 (7) |
C11 | 0.0843 (12) | 0.0277 (7) | 0.0410 (8) | −0.0040 (8) | −0.0127 (8) | 0.0052 (6) |
C12 | 0.0560 (9) | 0.0262 (6) | 0.0275 (6) | 0.0025 (6) | −0.0072 (6) | −0.0016 (5) |
C13 | 0.0441 (7) | 0.0338 (7) | 0.0285 (6) | 0.0099 (6) | −0.0032 (5) | −0.0065 (5) |
C14 | 0.0505 (9) | 0.0520 (9) | 0.0413 (8) | 0.0248 (7) | −0.0072 (6) | −0.0159 (7) |
C15 | 0.0377 (8) | 0.0845 (13) | 0.0471 (9) | 0.0201 (8) | 0.0032 (6) | −0.0218 (8) |
C16 | 0.0333 (7) | 0.0828 (13) | 0.0363 (7) | 0.0044 (8) | 0.0078 (6) | −0.0115 (8) |
C17 | 0.0318 (6) | 0.0492 (8) | 0.0328 (6) | 0.0028 (6) | 0.0080 (5) | −0.0026 (6) |
C18 | 0.0325 (6) | 0.0339 (6) | 0.0255 (5) | 0.0074 (5) | 0.0032 (5) | −0.0041 (5) |
C19 | 0.0295 (6) | 0.0294 (6) | 0.0273 (5) | −0.0052 (4) | 0.0089 (4) | −0.0013 (4) |
C20 | 0.0400 (7) | 0.0449 (8) | 0.0412 (7) | −0.0111 (6) | 0.0212 (6) | −0.0096 (6) |
C21 | 0.0385 (7) | 0.0537 (9) | 0.0468 (8) | −0.0122 (6) | 0.0216 (7) | −0.0035 (7) |
C22 | 0.0374 (7) | 0.0462 (8) | 0.0409 (7) | −0.0168 (6) | 0.0109 (6) | 0.0001 (6) |
C23 | 0.0401 (7) | 0.0352 (7) | 0.0306 (6) | −0.0108 (5) | 0.0074 (5) | −0.0036 (5) |
C24 | 0.0331 (6) | 0.0269 (5) | 0.0253 (5) | −0.0033 (4) | 0.0070 (5) | 0.0000 (4) |
C25 | 0.0334 (6) | 0.0246 (5) | 0.0244 (5) | −0.0008 (4) | 0.0074 (4) | −0.0004 (4) |
C26 | 0.0481 (8) | 0.0299 (6) | 0.0286 (6) | −0.0025 (5) | 0.0122 (5) | −0.0056 (5) |
C27 | 0.0538 (8) | 0.0380 (7) | 0.0349 (7) | 0.0021 (6) | 0.0230 (6) | −0.0055 (6) |
C28 | 0.0398 (7) | 0.0415 (7) | 0.0360 (7) | 0.0012 (6) | 0.0192 (6) | −0.0005 (5) |
C29 | 0.0314 (6) | 0.0326 (6) | 0.0286 (6) | −0.0004 (5) | 0.0104 (5) | −0.0020 (5) |
C30 | 0.0303 (5) | 0.0251 (5) | 0.0235 (5) | 0.0020 (4) | 0.0081 (4) | −0.0011 (4) |
S1' | 0.0766 (3) | 0.03097 (19) | 0.0802 (3) | 0.02280 (19) | 0.0414 (3) | 0.01087 (19) |
C1' | 0.0482 (8) | 0.0238 (6) | 0.0448 (7) | 0.0020 (5) | 0.0255 (6) | −0.0001 (5) |
N1' | 0.0704 (9) | 0.0251 (6) | 0.0722 (10) | 0.0047 (6) | 0.0376 (8) | −0.0031 (6) |
C2' | 0.0394 (7) | 0.0287 (6) | 0.0368 (6) | 0.0096 (5) | 0.0200 (5) | 0.0069 (5) |
N2' | 0.0522 (8) | 0.0397 (7) | 0.0536 (8) | 0.0206 (6) | 0.0245 (6) | 0.0123 (6) |
N3' | 0.0249 (5) | 0.0303 (5) | 0.0357 (5) | 0.0002 (4) | 0.0092 (4) | 0.0019 (4) |
C3' | 0.0294 (6) | 0.0308 (6) | 0.0310 (6) | 0.0041 (5) | 0.0108 (5) | 0.0005 (5) |
N4' | 0.0272 (5) | 0.0224 (4) | 0.0338 (5) | −0.0010 (4) | 0.0157 (4) | −0.0040 (4) |
C4' | 0.0282 (5) | 0.0222 (5) | 0.0290 (5) | 0.0009 (4) | 0.0131 (4) | −0.0010 (4) |
C5' | 0.0277 (5) | 0.0248 (5) | 0.0308 (6) | 0.0002 (4) | 0.0114 (5) | 0.0001 (4) |
C6' | 0.0379 (7) | 0.0271 (6) | 0.0415 (7) | −0.0041 (5) | 0.0150 (6) | −0.0061 (5) |
C7' | 0.0322 (6) | 0.0285 (6) | 0.0290 (6) | 0.0037 (5) | 0.0100 (5) | −0.0021 (4) |
C8' | 0.0369 (7) | 0.0348 (6) | 0.0358 (6) | 0.0036 (5) | 0.0159 (5) | 0.0014 (5) |
C9' | 0.0549 (9) | 0.0424 (8) | 0.0427 (8) | 0.0049 (7) | 0.0242 (7) | 0.0072 (6) |
C10' | 0.0633 (10) | 0.0469 (9) | 0.0405 (8) | 0.0145 (8) | 0.0173 (7) | 0.0128 (7) |
C11' | 0.0435 (8) | 0.0447 (8) | 0.0384 (7) | 0.0144 (6) | 0.0080 (6) | 0.0020 (6) |
C12' | 0.0334 (6) | 0.0344 (6) | 0.0321 (6) | 0.0058 (5) | 0.0087 (5) | −0.0049 (5) |
C13' | 0.0294 (6) | 0.0364 (6) | 0.0342 (6) | 0.0009 (5) | 0.0080 (5) | −0.0110 (5) |
C14' | 0.0293 (6) | 0.0512 (8) | 0.0422 (7) | 0.0030 (6) | 0.0079 (6) | −0.0179 (7) |
C15' | 0.0323 (7) | 0.0568 (9) | 0.0562 (9) | −0.0126 (6) | 0.0202 (7) | −0.0275 (8) |
C16' | 0.0426 (8) | 0.0466 (8) | 0.0564 (9) | −0.0157 (7) | 0.0258 (7) | −0.0173 (7) |
C17' | 0.0375 (7) | 0.0388 (7) | 0.0464 (8) | −0.0095 (6) | 0.0170 (6) | −0.0061 (6) |
C18' | 0.0271 (6) | 0.0342 (6) | 0.0357 (6) | −0.0038 (5) | 0.0102 (5) | −0.0079 (5) |
C19' | 0.0253 (5) | 0.0248 (5) | 0.0269 (5) | −0.0014 (4) | 0.0093 (4) | −0.0019 (4) |
C20' | 0.0315 (6) | 0.0353 (6) | 0.0374 (6) | −0.0022 (5) | 0.0175 (5) | −0.0041 (5) |
C21' | 0.0348 (7) | 0.0447 (8) | 0.0444 (7) | −0.0067 (6) | 0.0208 (6) | 0.0019 (6) |
C22' | 0.0366 (7) | 0.0342 (7) | 0.0496 (8) | −0.0099 (5) | 0.0146 (6) | 0.0020 (6) |
C23' | 0.0356 (6) | 0.0257 (6) | 0.0431 (7) | −0.0030 (5) | 0.0114 (6) | −0.0042 (5) |
C24' | 0.0263 (5) | 0.0255 (5) | 0.0277 (5) | 0.0006 (4) | 0.0079 (4) | −0.0029 (4) |
C25' | 0.0266 (5) | 0.0280 (5) | 0.0261 (5) | 0.0037 (4) | 0.0083 (4) | −0.0026 (4) |
C26' | 0.0399 (7) | 0.0401 (7) | 0.0333 (6) | 0.0104 (6) | 0.0135 (5) | −0.0071 (5) |
C27' | 0.0409 (7) | 0.0617 (10) | 0.0339 (7) | 0.0176 (7) | 0.0200 (6) | −0.0003 (6) |
C28' | 0.0334 (7) | 0.0604 (9) | 0.0366 (7) | 0.0097 (6) | 0.0201 (6) | 0.0124 (6) |
C29' | 0.0313 (6) | 0.0374 (7) | 0.0340 (6) | 0.0019 (5) | 0.0152 (5) | 0.0066 (5) |
C30' | 0.0244 (5) | 0.0284 (5) | 0.0260 (5) | 0.0035 (4) | 0.0098 (4) | 0.0002 (4) |
O1S | 0.056 (3) | 0.120 (5) | 0.124 (5) | 0.000 | 0.018 (3) | 0.000 |
S1—N1 | 1.6154 (14) | S1'—N1' | 1.6072 (17) |
S1—N2 | 1.6163 (13) | S1'—N2' | 1.6159 (16) |
N1—C1 | 1.3482 (16) | C1'—N1' | 1.3505 (17) |
C1—C6 | 1.4113 (18) | C1'—C6' | 1.413 (2) |
C1—C2 | 1.4278 (18) | C1'—C2' | 1.423 (2) |
C2—N2 | 1.3493 (16) | C2'—N2' | 1.3506 (17) |
C2—C3 | 1.4160 (17) | C2'—C3' | 1.4177 (18) |
N3—C7 | 1.3933 (17) | N3'—C7' | 1.3998 (17) |
N3—C18 | 1.4022 (17) | N3'—C18' | 1.4036 (16) |
N3—C5 | 1.4180 (15) | N3'—C5' | 1.4143 (15) |
C3—C4 | 1.3710 (17) | C3'—C4' | 1.3682 (17) |
N4—C19 | 1.4041 (15) | N4'—C30' | 1.3980 (15) |
N4—C30 | 1.4058 (16) | N4'—C19' | 1.3989 (15) |
N4—C4 | 1.4107 (14) | N4'—C4' | 1.4169 (15) |
C4—C5 | 1.4503 (16) | C4'—C5' | 1.4452 (16) |
C5—C6 | 1.3632 (16) | C5'—C6' | 1.3688 (17) |
C7—C8 | 1.382 (2) | C7'—C8' | 1.3898 (19) |
C7—C12 | 1.414 (2) | C7'—C12' | 1.4090 (18) |
C8—C9 | 1.395 (2) | C8'—C9' | 1.388 (2) |
C9—C10 | 1.402 (4) | C9'—C10' | 1.397 (2) |
C10—C11 | 1.362 (4) | C10'—C11' | 1.378 (3) |
C11—C12 | 1.399 (2) | C11'—C12' | 1.395 (2) |
C12—C13 | 1.440 (3) | C12'—C13' | 1.445 (2) |
C13—C18 | 1.4075 (19) | C13'—C18' | 1.4041 (19) |
C13—C14 | 1.410 (2) | C13'—C14' | 1.406 (2) |
C14—C15 | 1.377 (3) | C14'—C15' | 1.378 (3) |
C15—C16 | 1.388 (3) | C15'—C16' | 1.392 (3) |
C16—C17 | 1.388 (2) | C16'—C17' | 1.387 (2) |
C17—C18 | 1.391 (2) | C17'—C18' | 1.393 (2) |
C19—C20 | 1.3894 (19) | C19'—C20' | 1.3925 (17) |
C19—C24 | 1.4080 (17) | C19'—C24' | 1.4106 (16) |
C20—C21 | 1.389 (2) | C20'—C21' | 1.3890 (19) |
C21—C22 | 1.396 (2) | C21'—C22' | 1.394 (2) |
C22—C23 | 1.376 (2) | C22'—C23' | 1.381 (2) |
C23—C24 | 1.3933 (18) | C23'—C24' | 1.3944 (17) |
C24—C25 | 1.4394 (18) | C24'—C25' | 1.4395 (17) |
C25—C26 | 1.3931 (18) | C25'—C26' | 1.3947 (17) |
C25—C30 | 1.4033 (16) | C25'—C30' | 1.4051 (17) |
C26—C27 | 1.382 (2) | C26'—C27' | 1.382 (2) |
C27—C28 | 1.398 (2) | C27'—C28' | 1.395 (3) |
C28—C29 | 1.3877 (19) | C28'—C29' | 1.384 (2) |
C29—C30 | 1.3875 (18) | C29'—C30' | 1.3912 (17) |
N1—S1—N2 | 101.58 (6) | N1'—S1'—N2' | 101.38 (7) |
C1—N1—S1 | 105.58 (10) | N1'—C1'—C6' | 125.96 (15) |
N1—C1—C6 | 126.12 (12) | N1'—C1'—C2' | 113.50 (14) |
N1—C1—C2 | 113.77 (12) | C6'—C1'—C2' | 120.52 (12) |
C6—C1—C2 | 120.06 (11) | C1'—N1'—S1' | 106.00 (12) |
N2—C2—C3 | 126.17 (12) | N2'—C2'—C3' | 126.38 (14) |
N2—C2—C1 | 113.26 (11) | N2'—C2'—C1' | 113.23 (13) |
C3—C2—C1 | 120.55 (11) | C3'—C2'—C1' | 120.37 (12) |
C2—N2—S1 | 105.80 (10) | C2'—N2'—S1' | 105.89 (11) |
C7—N3—C18 | 108.81 (11) | C7'—N3'—C18' | 108.27 (10) |
C7—N3—C5 | 122.86 (11) | C7'—N3'—C5' | 125.13 (11) |
C18—N3—C5 | 127.14 (11) | C18'—N3'—C5' | 125.03 (11) |
C4—C3—C2 | 118.65 (11) | C4'—C3'—C2' | 118.43 (12) |
C19—N4—C30 | 107.94 (10) | C30'—N4'—C19' | 108.39 (9) |
C19—N4—C4 | 126.27 (10) | C30'—N4'—C4' | 124.67 (10) |
C30—N4—C4 | 125.68 (10) | C19'—N4'—C4' | 126.44 (10) |
C3—C4—N4 | 120.04 (11) | C3'—C4'—N4' | 119.71 (11) |
C3—C4—C5 | 120.36 (11) | C3'—C4'—C5' | 121.03 (11) |
N4—C4—C5 | 119.59 (10) | N4'—C4'—C5' | 119.26 (10) |
C6—C5—N3 | 118.40 (11) | C6'—C5'—N3' | 118.99 (12) |
C6—C5—C4 | 121.42 (11) | C6'—C5'—C4' | 121.08 (11) |
N3—C5—C4 | 120.01 (10) | N3'—C5'—C4' | 119.93 (10) |
C5—C6—C1 | 118.79 (11) | C5'—C6'—C1' | 118.49 (13) |
C8—C7—N3 | 128.78 (14) | C8'—C7'—N3' | 128.94 (12) |
C8—C7—C12 | 122.97 (14) | C8'—C7'—C12' | 122.23 (12) |
N3—C7—C12 | 108.23 (13) | N3'—C7'—C12' | 108.79 (12) |
C7—C8—C9 | 116.68 (19) | C9'—C8'—C7' | 117.35 (13) |
C8—C9—C10 | 121.1 (2) | C8'—C9'—C10' | 121.17 (16) |
C11—C10—C9 | 121.46 (16) | C11'—C10'—C9' | 121.09 (15) |
C10—C11—C12 | 119.32 (19) | C10'—C11'—C12' | 119.15 (14) |
C11—C12—C7 | 118.47 (18) | C11'—C12'—C7' | 119.00 (14) |
C11—C12—C13 | 134.15 (17) | C11'—C12'—C13' | 134.04 (13) |
C7—C12—C13 | 107.37 (12) | C7'—C12'—C13' | 106.91 (12) |
C18—C13—C14 | 118.56 (17) | C18'—C13'—C14' | 118.71 (14) |
C18—C13—C12 | 106.97 (13) | C18'—C13'—C12' | 107.22 (11) |
C14—C13—C12 | 134.41 (15) | C14'—C13'—C12' | 134.07 (14) |
C15—C14—C13 | 119.50 (16) | C15'—C14'—C13' | 119.17 (15) |
C14—C15—C16 | 120.77 (16) | C14'—C15'—C16' | 121.00 (14) |
C15—C16—C17 | 121.48 (19) | C17'—C16'—C15' | 121.44 (16) |
C16—C17—C18 | 117.77 (16) | C16'—C17'—C18' | 117.32 (15) |
C17—C18—N3 | 129.55 (12) | C17'—C18'—N3' | 128.97 (13) |
C17—C18—C13 | 121.85 (14) | C17'—C18'—C13' | 122.33 (13) |
N3—C18—C13 | 108.52 (13) | N3'—C18'—C13' | 108.68 (12) |
C20—C19—N4 | 130.04 (12) | C20'—C19'—N4' | 129.84 (11) |
C20—C19—C24 | 121.34 (12) | C20'—C19'—C24' | 121.60 (11) |
N4—C19—C24 | 108.60 (11) | N4'—C19'—C24' | 108.55 (10) |
C21—C20—C19 | 117.32 (14) | C21'—C20'—C19' | 117.13 (13) |
C20—C21—C22 | 121.82 (15) | C20'—C21'—C22' | 121.90 (13) |
C23—C22—C21 | 120.55 (13) | C23'—C22'—C21' | 120.78 (13) |
C22—C23—C24 | 118.90 (13) | C22'—C23'—C24' | 118.75 (13) |
C23—C24—C19 | 120.06 (12) | C23'—C24'—C19' | 119.85 (12) |
C23—C24—C25 | 132.61 (12) | C23'—C24'—C25' | 133.09 (12) |
C19—C24—C25 | 107.33 (10) | C19'—C24'—C25' | 107.06 (10) |
C26—C25—C30 | 119.70 (12) | C26'—C25'—C30' | 119.43 (12) |
C26—C25—C24 | 133.13 (12) | C26'—C25'—C24' | 133.38 (12) |
C30—C25—C24 | 107.14 (11) | C30'—C25'—C24' | 107.17 (10) |
C27—C26—C25 | 118.95 (12) | C27'—C26'—C25' | 118.83 (14) |
C26—C27—C28 | 120.68 (13) | C26'—C27'—C28' | 120.93 (13) |
C29—C28—C27 | 121.21 (13) | C29'—C28'—C27' | 121.46 (14) |
C30—C29—C28 | 117.68 (12) | C28'—C29'—C30' | 117.37 (13) |
C29—C30—C25 | 121.63 (11) | C29'—C30'—N4' | 129.21 (11) |
C29—C30—N4 | 129.37 (11) | C29'—C30'—C25' | 121.96 (11) |
C25—C30—N4 | 108.88 (11) | N4'—C30'—C25' | 108.78 (10) |
N2—S1—N1—C1 | 0.31 (12) | C6'—C1'—N1'—S1' | −178.50 (13) |
S1—N1—C1—C6 | −177.92 (12) | C2'—C1'—N1'—S1' | 0.19 (16) |
S1—N1—C1—C2 | −0.55 (15) | N2'—S1'—N1'—C1' | −0.34 (13) |
N1—C1—C2—N2 | 0.63 (17) | N1'—C1'—C2'—N2' | 0.08 (18) |
C6—C1—C2—N2 | 178.18 (13) | C6'—C1'—C2'—N2' | 178.85 (13) |
N1—C1—C2—C3 | 178.95 (12) | N1'—C1'—C2'—C3' | 178.81 (13) |
C6—C1—C2—C3 | −3.51 (19) | C6'—C1'—C2'—C3' | −2.4 (2) |
C3—C2—N2—S1 | −178.57 (11) | C3'—C2'—N2'—S1' | −178.95 (12) |
C1—C2—N2—S1 | −0.37 (15) | C1'—C2'—N2'—S1' | −0.31 (15) |
N1—S1—N2—C2 | 0.04 (12) | N1'—S1'—N2'—C2' | 0.38 (12) |
N2—C2—C3—C4 | 179.75 (13) | N2'—C2'—C3'—C4' | −179.63 (13) |
C1—C2—C3—C4 | 1.67 (19) | C1'—C2'—C3'—C4' | 1.82 (19) |
C2—C3—C4—N4 | −179.21 (11) | C2'—C3'—C4'—N4' | −178.77 (11) |
C2—C3—C4—C5 | 2.11 (18) | C2'—C3'—C4'—C5' | 0.62 (19) |
C19—N4—C4—C3 | −48.44 (18) | C30'—N4'—C4'—C3' | 114.22 (14) |
C30—N4—C4—C3 | 127.51 (13) | C19'—N4'—C4'—C3' | −56.71 (17) |
C19—N4—C4—C5 | 130.24 (13) | C30'—N4'—C4'—C5' | −65.19 (16) |
C30—N4—C4—C5 | −53.81 (17) | C19'—N4'—C4'—C5' | 123.89 (13) |
C7—N3—C5—C6 | 104.02 (14) | C7'—N3'—C5'—C6' | 110.74 (15) |
C18—N3—C5—C6 | −62.05 (17) | C18'—N3'—C5'—C6' | −53.26 (18) |
C7—N3—C5—C4 | −71.32 (16) | C7'—N3'—C5'—C4' | −69.28 (17) |
C18—N3—C5—C4 | 122.61 (13) | C18'—N3'—C5'—C4' | 126.72 (13) |
C3—C4—C5—C6 | −4.30 (19) | C3'—C4'—C5'—C6' | −2.62 (19) |
N4—C4—C5—C6 | 177.02 (12) | N4'—C4'—C5'—C6' | 176.77 (12) |
C3—C4—C5—N3 | 170.90 (11) | C3'—C4'—C5'—N3' | 177.40 (12) |
N4—C4—C5—N3 | −7.78 (17) | N4'—C4'—C5'—N3' | −3.21 (17) |
N3—C5—C6—C1 | −172.85 (12) | N3'—C5'—C6'—C1' | −178.01 (12) |
C4—C5—C6—C1 | 2.43 (19) | C4'—C5'—C6'—C1' | 2.0 (2) |
N1—C1—C6—C5 | 178.60 (13) | N1'—C1'—C6'—C5' | 179.06 (15) |
C2—C1—C6—C5 | 1.4 (2) | C2'—C1'—C6'—C5' | 0.5 (2) |
C18—N3—C7—C8 | 177.07 (13) | C18'—N3'—C7'—C8' | 176.16 (13) |
C5—N3—C7—C8 | 8.8 (2) | C5'—N3'—C7'—C8' | 9.9 (2) |
C18—N3—C7—C12 | −1.56 (14) | C18'—N3'—C7'—C12' | −1.68 (14) |
C5—N3—C7—C12 | −169.87 (11) | C5'—N3'—C7'—C12' | −167.94 (12) |
N3—C7—C8—C9 | −178.66 (14) | N3'—C7'—C8'—C9' | −177.53 (13) |
C12—C7—C8—C9 | −0.2 (2) | C12'—C7'—C8'—C9' | 0.1 (2) |
C7—C8—C9—C10 | 0.4 (2) | C7'—C8'—C9'—C10' | 0.6 (2) |
C8—C9—C10—C11 | −0.2 (3) | C8'—C9'—C10'—C11' | −0.7 (3) |
C9—C10—C11—C12 | −0.2 (3) | C9'—C10'—C11'—C12' | 0.1 (3) |
C10—C11—C12—C7 | 0.3 (2) | C10'—C11'—C12'—C7' | 0.5 (2) |
C10—C11—C12—C13 | 178.98 (16) | C10'—C11'—C12'—C13' | 177.82 (15) |
C8—C7—C12—C11 | −0.1 (2) | C8'—C7'—C12'—C11' | −0.6 (2) |
N3—C7—C12—C11 | 178.62 (12) | N3'—C7'—C12'—C11' | 177.39 (12) |
C8—C7—C12—C13 | −179.12 (13) | C8'—C7'—C12'—C13' | −178.59 (12) |
N3—C7—C12—C13 | −0.39 (14) | N3'—C7'—C12'—C13' | −0.57 (14) |
C11—C12—C13—C18 | −176.62 (15) | C11'—C12'—C13'—C18' | −174.93 (15) |
C7—C12—C13—C18 | 2.17 (14) | C7'—C12'—C13'—C18' | 2.59 (14) |
C11—C12—C13—C14 | 6.4 (3) | C11'—C12'—C13'—C14' | 5.4 (3) |
C7—C12—C13—C14 | −174.77 (15) | C7'—C12'—C13'—C14' | −177.12 (14) |
C18—C13—C14—C15 | −0.1 (2) | C18'—C13'—C14'—C15' | 2.0 (2) |
C12—C13—C14—C15 | 176.62 (15) | C12'—C13'—C14'—C15' | −178.35 (14) |
C13—C14—C15—C16 | 1.6 (2) | C13'—C14'—C15'—C16' | −0.2 (2) |
C14—C15—C16—C17 | −0.6 (3) | C14'—C15'—C16'—C17' | −1.3 (2) |
C15—C16—C17—C18 | −1.9 (2) | C15'—C16'—C17'—C18' | 0.9 (2) |
C16—C17—C18—N3 | −172.72 (13) | C16'—C17'—C18'—N3' | −177.21 (14) |
C16—C17—C18—C13 | 3.4 (2) | C16'—C17'—C18'—C13' | 1.0 (2) |
C7—N3—C18—C17 | 179.52 (13) | C7'—N3'—C18'—C17' | −178.27 (14) |
C5—N3—C18—C17 | −12.8 (2) | C5'—N3'—C18'—C17' | −12.0 (2) |
C7—N3—C18—C13 | 2.96 (14) | C7'—N3'—C18'—C13' | 3.34 (14) |
C5—N3—C18—C13 | 170.62 (11) | C5'—N3'—C18'—C13' | 169.62 (12) |
C14—C13—C18—C17 | −2.50 (19) | C14'—C13'—C18'—C17' | −2.4 (2) |
C12—C13—C18—C17 | 179.98 (12) | C12'—C13'—C18'—C17' | 177.83 (13) |
C14—C13—C18—N3 | 174.37 (12) | C14'—C13'—C18'—N3' | 176.11 (12) |
C12—C13—C18—N3 | −3.14 (14) | C12'—C13'—C18'—N3' | −3.65 (14) |
C30—N4—C19—C20 | −178.68 (14) | C30'—N4'—C19'—C20' | −178.97 (13) |
C4—N4—C19—C20 | −2.1 (2) | C4'—N4'—C19'—C20' | −6.8 (2) |
C30—N4—C19—C24 | 2.85 (14) | C30'—N4'—C19'—C24' | 2.27 (13) |
C4—N4—C19—C24 | 179.39 (11) | C4'—N4'—C19'—C24' | 174.42 (11) |
N4—C19—C20—C21 | −179.47 (14) | N4'—C19'—C20'—C21' | −178.58 (13) |
C24—C19—C20—C21 | −1.2 (2) | C24'—C19'—C20'—C21' | 0.03 (19) |
C19—C20—C21—C22 | 0.7 (2) | C19'—C20'—C21'—C22' | 0.1 (2) |
C20—C21—C22—C23 | 0.4 (3) | C20'—C21'—C22'—C23' | 0.0 (2) |
C21—C22—C23—C24 | −1.1 (2) | C21'—C22'—C23'—C24' | −0.3 (2) |
C22—C23—C24—C19 | 0.6 (2) | C22'—C23'—C24'—C19' | 0.4 (2) |
C22—C23—C24—C25 | −178.76 (14) | C22'—C23'—C24'—C25' | −178.75 (14) |
C20—C19—C24—C23 | 0.5 (2) | C20'—C19'—C24'—C23' | −0.31 (19) |
N4—C19—C24—C23 | 179.16 (12) | N4'—C19'—C24'—C23' | 178.57 (11) |
C20—C19—C24—C25 | −179.96 (13) | C20'—C19'—C24'—C25' | 179.05 (11) |
N4—C19—C24—C25 | −1.33 (14) | N4'—C19'—C24'—C25' | −2.07 (13) |
C23—C24—C25—C26 | 1.0 (2) | C23'—C24'—C25'—C26' | 1.7 (2) |
C19—C24—C25—C26 | −178.41 (14) | C19'—C24'—C25'—C26' | −177.59 (13) |
C23—C24—C25—C30 | 178.73 (14) | C23'—C24'—C25'—C30' | −179.66 (14) |
C19—C24—C25—C30 | −0.69 (14) | C19'—C24'—C25'—C30' | 1.10 (13) |
C30—C25—C26—C27 | −0.92 (19) | C30'—C25'—C26'—C27' | −1.04 (19) |
C24—C25—C26—C27 | 176.57 (14) | C24'—C25'—C26'—C27' | 177.52 (13) |
C25—C26—C27—C28 | −1.6 (2) | C25'—C26'—C27'—C28' | 0.2 (2) |
C26—C27—C28—C29 | 1.1 (2) | C26'—C27'—C28'—C29' | 0.5 (2) |
C27—C28—C29—C30 | 2.1 (2) | C27'—C28'—C29'—C30' | −0.3 (2) |
C28—C29—C30—C25 | −4.68 (19) | C28'—C29'—C30'—N4' | −178.05 (12) |
C28—C29—C30—N4 | 179.79 (12) | C28'—C29'—C30'—C25' | −0.61 (19) |
C26—C25—C30—C29 | 4.19 (18) | C19'—N4'—C30'—C29' | 176.13 (12) |
C24—C25—C30—C29 | −173.90 (11) | C4'—N4'—C30'—C29' | 3.8 (2) |
C26—C25—C30—N4 | −179.46 (11) | C19'—N4'—C30'—C25' | −1.57 (13) |
C24—C25—C30—N4 | 2.46 (13) | C4'—N4'—C30'—C25' | −173.89 (11) |
C19—N4—C30—C29 | 172.68 (12) | C26'—C25'—C30'—C29' | 1.28 (18) |
C4—N4—C30—C29 | −3.9 (2) | C24'—C25'—C30'—C29' | −177.63 (11) |
C19—N4—C30—C25 | −3.30 (13) | C26'—C25'—C30'—N4' | 179.18 (11) |
C4—N4—C30—C25 | −179.87 (11) | C24'—C25'—C30'—N4' | 0.28 (13) |
X-ray | Optimized experimental structure | Optimized structure 1 | Optimized structure 2 | |
Space group | P1 | P1 | C2 | C2 |
a (Å) | 8.36 | 8.01 | 13.94 | 13.52 |
b (Å) | 8.73 | 8.64 | 10.39 | 10.61 |
c (Å) | 8.86 | 8.75 | 9.32 | 8.61 |
α (°) | 104.4 | 104.1 | 90.0 | 90.0 |
β (°) | 94.2 | 94.7 | 125.8 | 106.2 |
γ (°) | 112.3 | 112.8 | 90.0 | 90.0 |
S1—N1, S1—N2 (Å) | 1.616, 1.614 | 1.620, 1.618 | 1.619 | 1.619 |
N1—C1, N2—C2 (Å) | 1.347, 1.350 | 1.351, 1.350 | 1.349 | 1.350 |
C1—C2 (Å) | 1.433 | 1.445 | 1.443 | 1.444 |
C1—C6, C2—C3 (Å) | 1.421, 1.417 | 1.413, 1.413 | 1.414 | 1.410 |
C3—C4, C5—C6 (Å) | 1.366, 1.363 | 1.375,1.376 | 1.374 | 1.376 |
C4—C5 (Å) | 1.452 | 1.442 | 1.445 | 1.443 |
C4—N4, C5—N3 (Å) | 1.415, 1.415 | 1.411, 1.408 | 1.411 | 1.410 |
DFBT–Carbazole dihedral angle (°) | 67.3, 69.9 | 64.4, 66.7 | 63.3 | 64.6 |