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Nucleophilic substitution of F atoms in 5,6-di­fluorobenzo[c][1,2,5]thiadiazole (DFBT) for carbazole could be potentially inter­esting as a novel way of synthesizing building blocks for new conjugated materials for applications in organic chemistry. The crystal structures of 5,6-bis­(9H-carbazol-9-yl)ben­zo[c][1,2,5]thia­diazole (DCBT), C30H18N4S, and its hydrate, C30H18N4S·0.125H2O, were investigated using single-crystal X-ray analysis. The hydrate contains two symmetry-independent DCBT mol­ecules. The dihedral angles between the plane of the central benzo­thia­diazole fragment and that of the carbazole units vary between 50.8 and 69.9°, indicating conformational flexibility of the DCBT mol­ecule in the crystals, which is consistent with quantum chemical calculations. The analysis of the crystal packing of DCBT revealed that the experimental triclinic structure could be described as a distortion from a hypothetical higher-symmetry monoclinic structure. The quantum chemical calculations of two possible monoclinic structures, which are related to the experimental structure by a shifting of mol­ecular layers, showed that the proposed structures are higher in energy by 5.4 and 10.1 kcal mol−1. This energy increase is caused by less dense crystal packings of the symmetric structures, which results in a decrease of the number of inter­molecular inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617003035/yf3115sup1.cif
Contains datablocks I, Ia, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617003035/yf3115Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617003035/yf3115Iasup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617003035/yf3115Isup4.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617003035/yf3115sup5.pdf
Additional figures, and comparison tables of geometrical parameters for benzothiadiazole and carbazole fragments

txt

Text file https://doi.org/10.1107/S2053229617003035/yf3115sup6.txt
Refinement instructions for structures 1 and 2

CCDC references: 1534363; 1534362

Computing details top

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).

(I) 5,6-Bis(9H-carbazol-9-yl)benzo[c][1,2,5]thiadiazole top
Crystal data top
C30H18N4SZ = 1
Mr = 466.54F(000) = 242
Triclinic, P1Dx = 1.362 Mg m3
a = 8.3617 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.7261 (8) ÅCell parameters from 6909 reflections
c = 8.8590 (8) Åθ = 2.4–32.1°
α = 104.451 (1)°µ = 0.17 mm1
β = 94.187 (1)°T = 215 K
γ = 112.344 (1)°Prism, yellow
V = 568.69 (9) Å30.4 × 0.3 × 0.2 mm
Data collection top
Bruker APEXII CCD
diffractometer
6746 reflections with I > 2σ(I)
φ and ω scansRint = 0.018
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 32.1°, θmin = 2.4°
Tmin = 0.673, Tmax = 0.746h = 1212
9318 measured reflectionsk = 1212
7051 independent reflectionsl = 1312
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll 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 = 1.04Δρmax = 0.23 e Å3
7051 reflectionsΔρmin = 0.32 e Å3
388 parametersAbsolute structure: Flack x determined using 3101 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraintsAbsolute structure parameter: 0.038 (17)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.49611 (6)0.80527 (6)0.74131 (5)0.04375 (13)
C10.4137 (2)0.5379 (2)0.53948 (18)0.0282 (3)
N10.3503 (2)0.6086 (2)0.66070 (19)0.0381 (3)
C20.5826 (2)0.6541 (2)0.52381 (19)0.0277 (3)
N20.6439 (2)0.8122 (2)0.6326 (2)0.0377 (3)
N30.3303 (2)0.15250 (17)0.20087 (16)0.0283 (3)
C30.6718 (2)0.5973 (2)0.4072 (2)0.0286 (3)
H30.785 (4)0.664 (4)0.401 (3)0.042 (7)*
N40.6788 (2)0.36446 (18)0.19717 (16)0.0282 (3)
C40.5900 (2)0.43122 (18)0.30775 (17)0.0247 (3)
C50.4134 (2)0.31763 (18)0.31611 (17)0.0250 (3)
C60.3278 (2)0.3680 (2)0.43058 (19)0.0291 (3)
H60.211 (4)0.290 (4)0.436 (3)0.041 (7)*
C70.2784 (2)0.1259 (2)0.03953 (18)0.0275 (3)
C80.2783 (2)0.2470 (2)0.0369 (2)0.0345 (3)
H80.321 (4)0.375 (4)0.027 (3)0.047 (7)*
C90.2071 (3)0.1843 (3)0.1981 (2)0.0418 (4)
H90.202 (4)0.269 (4)0.253 (4)0.049 (8)*
C100.1359 (3)0.0071 (3)0.2787 (2)0.0435 (4)
H100.069 (5)0.045 (5)0.399 (4)0.060 (9)*
C110.1353 (2)0.1134 (3)0.2020 (2)0.0368 (4)
H110.082 (4)0.240 (4)0.262 (3)0.042 (7)*
C120.2081 (2)0.0541 (2)0.03998 (18)0.0288 (3)
C130.2171 (2)0.1396 (2)0.0787 (2)0.0288 (3)
C140.1645 (3)0.3138 (2)0.0737 (3)0.0412 (4)
H140.118 (5)0.408 (5)0.025 (4)0.055 (8)*
C150.1799 (3)0.3528 (3)0.2143 (3)0.0488 (5)
H150.128 (5)0.475 (5)0.217 (4)0.055 (8)*
C160.2484 (3)0.2215 (3)0.3593 (3)0.0442 (4)
H160.254 (5)0.250 (5)0.458 (4)0.057 (8)*
C170.3061 (3)0.0466 (2)0.3683 (2)0.0350 (3)
H170.352 (4)0.048 (4)0.481 (3)0.038 (6)*
C180.2894 (2)0.00871 (19)0.22618 (19)0.0274 (3)
C190.7079 (2)0.3993 (2)0.05368 (18)0.0272 (3)
C200.6842 (2)0.5257 (2)0.0026 (2)0.0342 (3)
H200.648 (4)0.610 (4)0.064 (4)0.043 (7)*
C210.7262 (3)0.5344 (3)0.1496 (2)0.0422 (4)
H210.721 (5)0.626 (5)0.193 (4)0.059 (9)*
C220.7865 (3)0.4180 (3)0.2394 (2)0.0447 (5)
H220.813 (4)0.442 (5)0.341 (4)0.055 (8)*
C230.8104 (3)0.2922 (3)0.1825 (2)0.0384 (4)
H230.850 (4)0.216 (4)0.242 (4)0.056 (8)*
C240.7734 (2)0.2838 (2)0.03248 (19)0.0286 (3)
C250.7896 (2)0.17885 (19)0.06540 (19)0.0275 (3)
C260.8553 (2)0.0510 (2)0.0500 (2)0.0345 (3)
H260.897 (4)0.008 (4)0.050 (4)0.050 (8)*
C270.8594 (3)0.0192 (2)0.1735 (3)0.0402 (4)
H270.910 (4)0.105 (4)0.167 (4)0.052 (8)*
C280.7977 (3)0.0342 (3)0.3117 (3)0.0403 (4)
H280.797 (4)0.017 (4)0.397 (4)0.043 (7)*
C290.7311 (3)0.1601 (2)0.3295 (2)0.0341 (3)
H290.697 (5)0.206 (5)0.421 (4)0.058 (9)*
C300.7290 (2)0.23084 (19)0.20523 (19)0.0275 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0424 (2)0.0442 (2)0.0356 (2)0.02533 (19)0.00061 (17)0.01320 (17)
C10.0324 (7)0.0303 (7)0.0242 (6)0.0185 (6)0.0053 (5)0.0031 (5)
N10.0405 (8)0.0427 (8)0.0306 (7)0.0241 (7)0.0077 (6)0.0015 (6)
C20.0323 (7)0.0235 (6)0.0276 (6)0.0160 (5)0.0023 (5)0.0018 (5)
N20.0380 (7)0.0297 (7)0.0385 (7)0.0184 (6)0.0001 (6)0.0064 (6)
N30.0369 (7)0.0205 (5)0.0241 (5)0.0106 (5)0.0050 (5)0.0027 (4)
C30.0315 (7)0.0223 (6)0.0317 (7)0.0128 (5)0.0076 (6)0.0043 (5)
N40.0385 (7)0.0251 (6)0.0283 (6)0.0193 (5)0.0142 (5)0.0085 (5)
C40.0318 (7)0.0210 (6)0.0247 (6)0.0143 (5)0.0086 (5)0.0059 (5)
C50.0307 (7)0.0204 (6)0.0239 (6)0.0121 (5)0.0054 (5)0.0037 (5)
C60.0314 (7)0.0267 (7)0.0283 (7)0.0129 (6)0.0084 (6)0.0047 (5)
C70.0269 (6)0.0290 (7)0.0245 (6)0.0112 (5)0.0068 (5)0.0046 (5)
C80.0344 (8)0.0363 (8)0.0316 (7)0.0115 (7)0.0070 (6)0.0129 (6)
C90.0366 (9)0.0571 (12)0.0326 (8)0.0156 (8)0.0090 (7)0.0203 (8)
C100.0362 (9)0.0620 (13)0.0264 (7)0.0168 (8)0.0063 (6)0.0086 (8)
C110.0309 (8)0.0429 (9)0.0273 (7)0.0140 (7)0.0045 (6)0.0028 (7)
C120.0257 (6)0.0308 (7)0.0258 (6)0.0128 (6)0.0049 (5)0.0003 (5)
C130.0269 (6)0.0237 (6)0.0326 (7)0.0129 (5)0.0027 (5)0.0002 (5)
C140.0430 (9)0.0228 (7)0.0504 (10)0.0149 (7)0.0034 (8)0.0005 (7)
C150.0553 (12)0.0258 (8)0.0621 (13)0.0170 (8)0.0019 (10)0.0110 (8)
C160.0523 (11)0.0348 (9)0.0484 (11)0.0197 (8)0.0031 (9)0.0167 (8)
C170.0414 (9)0.0303 (7)0.0333 (8)0.0156 (7)0.0044 (7)0.0092 (6)
C180.0304 (7)0.0216 (6)0.0296 (7)0.0124 (5)0.0049 (5)0.0040 (5)
C190.0296 (7)0.0252 (6)0.0255 (6)0.0106 (5)0.0075 (5)0.0060 (5)
C200.0367 (8)0.0315 (7)0.0359 (8)0.0140 (6)0.0071 (6)0.0126 (6)
C210.0441 (10)0.0448 (10)0.0351 (9)0.0123 (8)0.0039 (7)0.0183 (8)
C220.0502 (11)0.0477 (11)0.0257 (8)0.0099 (9)0.0070 (7)0.0096 (7)
C230.0402 (9)0.0379 (9)0.0262 (7)0.0096 (7)0.0098 (6)0.0005 (6)
C240.0280 (7)0.0250 (6)0.0263 (6)0.0076 (5)0.0071 (5)0.0014 (5)
C250.0254 (6)0.0217 (6)0.0310 (7)0.0090 (5)0.0079 (5)0.0009 (5)
C260.0276 (7)0.0246 (7)0.0470 (9)0.0119 (6)0.0111 (6)0.0004 (6)
C270.0331 (8)0.0281 (7)0.0629 (12)0.0175 (6)0.0109 (8)0.0110 (8)
C280.0396 (9)0.0335 (8)0.0567 (11)0.0203 (7)0.0122 (8)0.0195 (8)
C290.0407 (8)0.0314 (7)0.0379 (8)0.0202 (7)0.0133 (7)0.0132 (6)
C300.0310 (7)0.0217 (6)0.0311 (7)0.0134 (5)0.0094 (6)0.0050 (5)
Geometric parameters (Å, º) top
S1—N21.6137 (19)C11—C121.400 (2)
S1—N11.6161 (19)C12—C131.446 (2)
C1—N11.347 (2)C13—C141.400 (2)
C1—C61.421 (2)C13—C181.411 (2)
C1—C21.433 (2)C14—C151.381 (3)
C2—N21.350 (2)C15—C161.397 (3)
C2—C31.417 (2)C16—C171.394 (3)
N3—C181.3960 (19)C17—C181.390 (2)
N3—C71.397 (2)C19—C201.389 (2)
N3—C51.4150 (19)C19—C241.412 (2)
C3—C41.366 (2)C20—C211.386 (3)
N4—C191.396 (2)C21—C221.401 (3)
N4—C301.3962 (19)C22—C231.389 (3)
N4—C41.4147 (18)C23—C241.400 (2)
C4—C51.452 (2)C24—C251.443 (2)
C5—C61.363 (2)C25—C261.402 (2)
C7—C81.389 (2)C25—C301.408 (2)
C7—C121.412 (2)C26—C271.384 (3)
C8—C91.390 (3)C27—C281.404 (3)
C9—C101.394 (3)C28—C291.390 (2)
C10—C111.386 (3)C29—C301.392 (2)
N2—S1—N1101.31 (8)C7—C12—C13106.97 (13)
N1—C1—C6126.37 (16)C14—C13—C18119.34 (17)
N1—C1—C2113.35 (15)C14—C13—C12133.66 (16)
C6—C1—C2120.26 (14)C18—C13—C12106.94 (13)
C1—N1—S1106.05 (13)C15—C14—C13118.82 (18)
N2—C2—C3126.24 (16)C14—C15—C16120.92 (18)
N2—C2—C1113.16 (15)C17—C16—C15121.75 (19)
C3—C2—C1120.55 (14)C18—C17—C16116.88 (17)
C2—N2—S1106.11 (13)C17—C18—N3128.99 (15)
C18—N3—C7108.70 (13)C17—C18—C13122.27 (15)
C18—N3—C5126.86 (13)N3—C18—C13108.70 (14)
C7—N3—C5124.43 (13)C20—C19—N4128.98 (15)
C4—C3—C2118.17 (14)C20—C19—C24122.38 (15)
C19—N4—C30108.60 (12)N4—C19—C24108.62 (14)
C19—N4—C4127.14 (13)C21—C20—C19117.33 (18)
C30—N4—C4123.65 (13)C20—C21—C22121.35 (19)
C3—C4—N4120.24 (14)C23—C22—C21121.12 (17)
C3—C4—C5121.23 (13)C22—C23—C24118.58 (18)
N4—C4—C5118.50 (13)C23—C24—C19119.20 (17)
C6—C5—N3120.27 (14)C23—C24—C25133.84 (17)
C6—C5—C4121.36 (13)C19—C24—C25106.95 (14)
N3—C5—C4118.36 (13)C26—C25—C30119.01 (16)
C5—C6—C1118.19 (14)C26—C25—C24133.93 (16)
C8—C7—N3128.67 (15)C30—C25—C24107.02 (13)
C8—C7—C12122.52 (15)C27—C26—C25118.79 (16)
N3—C7—C12108.63 (14)C26—C27—C28121.24 (16)
C7—C8—C9117.21 (18)C29—C28—C27121.11 (18)
C8—C9—C10121.2 (2)C28—C29—C30117.19 (17)
C11—C10—C9121.41 (18)C29—C30—N4128.49 (14)
C10—C11—C12118.65 (18)C29—C30—C25122.66 (14)
C11—C12—C7118.95 (16)N4—C30—C25108.78 (14)
C11—C12—C13133.84 (16)
C6—C1—N1—S1177.72 (14)C18—C13—C14—C152.0 (3)
C2—C1—N1—S10.72 (18)C12—C13—C14—C15174.7 (2)
N2—S1—N1—C10.48 (15)C13—C14—C15—C160.7 (4)
N1—C1—C2—N20.7 (2)C14—C15—C16—C170.9 (4)
C6—C1—C2—N2177.83 (15)C15—C16—C17—C181.1 (3)
N1—C1—C2—C3176.81 (15)C16—C17—C18—N3177.63 (18)
C6—C1—C2—C34.6 (2)C16—C17—C18—C130.2 (3)
C3—C2—N2—S1177.03 (14)C7—N3—C18—C17175.24 (17)
C1—C2—N2—S10.33 (17)C5—N3—C18—C175.8 (3)
N1—S1—N2—C20.08 (14)C7—N3—C18—C132.43 (18)
N2—C2—C3—C4179.17 (16)C5—N3—C18—C13176.51 (15)
C1—C2—C3—C42.0 (2)C14—C13—C18—C171.8 (3)
C2—C3—C4—N4175.38 (14)C12—C13—C18—C17175.70 (16)
C2—C3—C4—C52.6 (2)C14—C13—C18—N3179.70 (16)
C19—N4—C4—C377.0 (2)C12—C13—C18—N32.16 (17)
C30—N4—C4—C3112.99 (18)C30—N4—C19—C20177.15 (17)
C19—N4—C4—C5104.96 (18)C4—N4—C19—C2011.6 (3)
C30—N4—C4—C565.0 (2)C30—N4—C19—C241.39 (18)
C18—N3—C5—C668.9 (2)C4—N4—C19—C24169.82 (15)
C7—N3—C5—C6112.30 (18)N4—C19—C20—C21178.93 (18)
C18—N3—C5—C4111.72 (18)C24—C19—C20—C210.6 (3)
C7—N3—C5—C467.1 (2)C19—C20—C21—C221.3 (3)
C3—C4—C5—C64.7 (2)C20—C21—C22—C231.6 (3)
N4—C4—C5—C6173.24 (14)C21—C22—C23—C240.2 (3)
C3—C4—C5—N3174.60 (14)C22—C23—C24—C192.0 (3)
N4—C4—C5—N37.4 (2)C22—C23—C24—C25176.78 (18)
N3—C5—C6—C1177.31 (14)C20—C19—C24—C232.2 (2)
C4—C5—C6—C12.0 (2)N4—C19—C24—C23179.10 (15)
N1—C1—C6—C5179.13 (16)C20—C19—C24—C25176.82 (16)
C2—C1—C6—C52.5 (2)N4—C19—C24—C251.84 (17)
C18—N3—C7—C8173.43 (16)C23—C24—C25—C263.2 (3)
C5—N3—C7—C87.6 (3)C19—C24—C25—C26175.67 (17)
C18—N3—C7—C121.72 (18)C23—C24—C25—C30179.54 (18)
C5—N3—C7—C12177.25 (14)C19—C24—C25—C301.59 (17)
N3—C7—C8—C9175.27 (17)C30—C25—C26—C270.4 (2)
C12—C7—C8—C90.7 (2)C24—C25—C26—C27176.59 (17)
C7—C8—C9—C101.2 (3)C25—C26—C27—C280.6 (3)
C8—C9—C10—C110.9 (3)C26—C27—C28—C290.3 (3)
C9—C10—C11—C120.1 (3)C27—C28—C29—C300.3 (3)
C10—C11—C12—C70.4 (2)C28—C29—C30—N4176.04 (18)
C10—C11—C12—C13173.87 (18)C28—C29—C30—C250.5 (3)
C8—C7—C12—C110.0 (2)C19—N4—C30—C29176.53 (17)
N3—C7—C12—C11175.46 (14)C4—N4—C30—C2911.9 (3)
C8—C7—C12—C13175.14 (15)C19—N4—C30—C250.37 (18)
N3—C7—C12—C130.37 (17)C4—N4—C30—C25171.21 (15)
C11—C12—C13—C144.1 (3)C26—C25—C30—C290.1 (2)
C7—C12—C13—C14178.1 (2)C24—C25—C30—C29177.88 (15)
C11—C12—C13—C18172.95 (17)C26—C25—C30—N4176.98 (14)
C7—C12—C13—C181.09 (17)C24—C25—C30—N40.76 (18)
(Ia) 5,6-Bis(9H-carbazol-9-yl)benzo[c][1,2,5]thiadiazole 0.125-hydrate top
Crystal data top
C30H18N4S·0.125H2OF(000) = 3892
Mr = 468.79Dx = 1.380 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 28.338 (3) ÅCell parameters from 5147 reflections
b = 12.9466 (12) Åθ = 2.6–31.7°
c = 26.799 (3) ŵ = 0.17 mm1
β = 113.336 (1)°T = 215 K
V = 9027.7 (14) Å3Prism, yelllow
Z = 160.4 × 0.3 × 0.3 mm
Data collection top
Bruker APEXII CCD
diffractometer
10976 reflections with I > 2σ(I)
φ and ω scansRint = 0.031
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 30.2°, θmin = 1.6°
Tmin = 0.681, Tmax = 0.746h = 3939
67947 measured reflectionsk = 1818
13333 independent reflectionsl = 3737
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048H 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 reflectionsΔρmax = 0.48 e Å3
780 parametersΔρmin = 0.53 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.02474 (2)1.13995 (3)0.19311 (2)0.04780 (11)
N10.07218 (5)1.05989 (10)0.20898 (5)0.0421 (3)
C10.05468 (5)0.98031 (10)0.17401 (5)0.0311 (2)
C20.00249 (5)0.99161 (10)0.13663 (5)0.0304 (2)
N20.01920 (5)1.08059 (9)0.14316 (6)0.0414 (3)
N30.08419 (4)0.72000 (8)0.13943 (4)0.0311 (2)
C30.02123 (5)0.91522 (10)0.09670 (5)0.0297 (2)
H30.0563 (6)0.9268 (13)0.0692 (7)0.039 (4)*
N40.01579 (4)0.75220 (8)0.05592 (4)0.0287 (2)
C40.00651 (4)0.82911 (9)0.09562 (5)0.0261 (2)
C50.05845 (5)0.81539 (9)0.13586 (5)0.0266 (2)
C60.08224 (5)0.88987 (10)0.17338 (5)0.0315 (2)
H60.1154 (7)0.8784 (14)0.1998 (7)0.041 (4)*
C70.07087 (6)0.63017 (10)0.15940 (5)0.0362 (3)
C80.02895 (7)0.61231 (14)0.17233 (6)0.0471 (4)
H80.0036 (8)0.6608 (16)0.1698 (8)0.050 (5)*
C90.02562 (9)0.51479 (17)0.19285 (7)0.0657 (6)
H90.0024 (9)0.4987 (18)0.2021 (9)0.065 (6)*
C100.06337 (10)0.43952 (15)0.20010 (8)0.0714 (6)
H100.0604 (9)0.374 (2)0.2151 (10)0.081 (7)*
C110.10453 (9)0.45852 (12)0.18729 (7)0.0627 (5)
H110.1322 (8)0.4036 (18)0.1939 (9)0.067 (6)*
C120.10923 (6)0.55511 (10)0.16633 (6)0.0440 (4)
C130.14680 (6)0.60132 (11)0.14956 (5)0.0410 (3)
C140.19106 (7)0.56484 (15)0.14338 (7)0.0558 (4)
H140.2002 (8)0.4977 (18)0.1533 (9)0.063 (6)*
C150.21774 (7)0.63001 (18)0.12331 (7)0.0607 (4)
H150.2494 (8)0.6013 (17)0.1197 (8)0.060 (6)*
C160.20229 (6)0.73171 (17)0.11036 (7)0.0526 (4)
H160.2240 (9)0.7814 (19)0.0948 (10)0.074 (7)*
C170.15941 (5)0.77099 (13)0.11663 (6)0.0395 (3)
H170.1488 (7)0.8435 (15)0.1083 (8)0.049 (5)*
C180.13128 (5)0.70408 (10)0.13490 (5)0.0333 (3)
C190.06438 (5)0.70704 (10)0.04218 (5)0.0295 (2)
C200.10084 (6)0.72293 (12)0.06399 (6)0.0404 (3)
H200.0951 (7)0.7707 (15)0.0922 (8)0.048 (5)*
C210.14596 (6)0.66586 (14)0.04224 (7)0.0449 (3)
H210.1720 (8)0.6772 (15)0.0559 (8)0.053 (5)*
C220.15450 (6)0.59437 (13)0.00054 (6)0.0429 (3)
H220.1866 (7)0.5575 (15)0.0140 (8)0.052 (5)*
C230.11784 (6)0.57771 (11)0.02024 (6)0.0374 (3)
H230.1231 (7)0.5301 (15)0.0491 (8)0.048 (5)*
C240.07242 (5)0.63462 (9)0.00040 (5)0.0299 (2)
C250.02786 (5)0.63715 (9)0.01273 (5)0.0287 (2)
C260.01474 (6)0.58505 (11)0.05090 (5)0.0365 (3)
H260.0371 (7)0.5330 (14)0.0733 (7)0.042 (4)*
C270.03096 (6)0.60930 (12)0.05529 (6)0.0405 (3)
H270.0413 (7)0.5710 (14)0.0810 (8)0.045 (5)*
C280.06298 (6)0.68673 (12)0.02298 (6)0.0378 (3)
H280.0948 (7)0.7012 (13)0.0269 (7)0.041 (4)*
C290.05034 (5)0.74014 (10)0.01491 (5)0.0313 (2)
H290.0723 (6)0.7958 (13)0.0363 (7)0.037 (4)*
C300.00566 (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)
O1S0.00000.8921 (5)0.25000.1051 (18)0.5
H1SA0.02250.85330.27280.126*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0519 (2)0.03475 (18)0.0598 (2)0.00234 (15)0.02537 (19)0.02004 (16)
N10.0442 (7)0.0349 (6)0.0454 (7)0.0065 (5)0.0158 (5)0.0155 (5)
C10.0333 (6)0.0276 (6)0.0329 (6)0.0046 (5)0.0135 (5)0.0072 (5)
C20.0318 (6)0.0276 (6)0.0353 (6)0.0006 (4)0.0169 (5)0.0043 (5)
N20.0416 (6)0.0341 (6)0.0527 (7)0.0026 (5)0.0231 (6)0.0107 (5)
N30.0347 (5)0.0243 (5)0.0316 (5)0.0018 (4)0.0103 (4)0.0008 (4)
C30.0267 (5)0.0314 (6)0.0304 (6)0.0002 (4)0.0108 (5)0.0039 (5)
N40.0278 (5)0.0300 (5)0.0278 (5)0.0050 (4)0.0104 (4)0.0075 (4)
C40.0275 (5)0.0260 (5)0.0250 (5)0.0036 (4)0.0108 (4)0.0038 (4)
C50.0281 (5)0.0244 (5)0.0267 (5)0.0002 (4)0.0102 (4)0.0010 (4)
C60.0282 (6)0.0305 (6)0.0311 (6)0.0014 (5)0.0069 (5)0.0045 (5)
C70.0468 (7)0.0265 (6)0.0246 (5)0.0054 (5)0.0026 (5)0.0005 (4)
C80.0562 (9)0.0442 (8)0.0336 (7)0.0152 (7)0.0100 (6)0.0025 (6)
C90.0814 (14)0.0631 (12)0.0373 (8)0.0371 (11)0.0071 (8)0.0083 (8)
C100.1002 (14)0.0388 (9)0.0417 (9)0.0239 (10)0.0076 (9)0.0138 (7)
C110.0843 (12)0.0277 (7)0.0410 (8)0.0040 (8)0.0127 (8)0.0052 (6)
C120.0560 (9)0.0262 (6)0.0275 (6)0.0025 (6)0.0072 (6)0.0016 (5)
C130.0441 (7)0.0338 (7)0.0285 (6)0.0099 (6)0.0032 (5)0.0065 (5)
C140.0505 (9)0.0520 (9)0.0413 (8)0.0248 (7)0.0072 (6)0.0159 (7)
C150.0377 (8)0.0845 (13)0.0471 (9)0.0201 (8)0.0032 (6)0.0218 (8)
C160.0333 (7)0.0828 (13)0.0363 (7)0.0044 (8)0.0078 (6)0.0115 (8)
C170.0318 (6)0.0492 (8)0.0328 (6)0.0028 (6)0.0080 (5)0.0026 (6)
C180.0325 (6)0.0339 (6)0.0255 (5)0.0074 (5)0.0032 (5)0.0041 (5)
C190.0295 (6)0.0294 (6)0.0273 (5)0.0052 (4)0.0089 (4)0.0013 (4)
C200.0400 (7)0.0449 (8)0.0412 (7)0.0111 (6)0.0212 (6)0.0096 (6)
C210.0385 (7)0.0537 (9)0.0468 (8)0.0122 (6)0.0216 (7)0.0035 (7)
C220.0374 (7)0.0462 (8)0.0409 (7)0.0168 (6)0.0109 (6)0.0001 (6)
C230.0401 (7)0.0352 (7)0.0306 (6)0.0108 (5)0.0074 (5)0.0036 (5)
C240.0331 (6)0.0269 (5)0.0253 (5)0.0033 (4)0.0070 (5)0.0000 (4)
C250.0334 (6)0.0246 (5)0.0244 (5)0.0008 (4)0.0074 (4)0.0004 (4)
C260.0481 (8)0.0299 (6)0.0286 (6)0.0025 (5)0.0122 (5)0.0056 (5)
C270.0538 (8)0.0380 (7)0.0349 (7)0.0021 (6)0.0230 (6)0.0055 (6)
C280.0398 (7)0.0415 (7)0.0360 (7)0.0012 (6)0.0192 (6)0.0005 (5)
C290.0314 (6)0.0326 (6)0.0286 (6)0.0004 (5)0.0104 (5)0.0020 (5)
C300.0303 (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)
O1S0.056 (3)0.120 (5)0.124 (5)0.0000.018 (3)0.000
Geometric parameters (Å, º) top
S1—N11.6154 (14)S1'—N1'1.6072 (17)
S1—N21.6163 (13)S1'—N2'1.6159 (16)
N1—C11.3482 (16)C1'—N1'1.3505 (17)
C1—C61.4113 (18)C1'—C6'1.413 (2)
C1—C21.4278 (18)C1'—C2'1.423 (2)
C2—N21.3493 (16)C2'—N2'1.3506 (17)
C2—C31.4160 (17)C2'—C3'1.4177 (18)
N3—C71.3933 (17)N3'—C7'1.3998 (17)
N3—C181.4022 (17)N3'—C18'1.4036 (16)
N3—C51.4180 (15)N3'—C5'1.4143 (15)
C3—C41.3710 (17)C3'—C4'1.3682 (17)
N4—C191.4041 (15)N4'—C30'1.3980 (15)
N4—C301.4058 (16)N4'—C19'1.3989 (15)
N4—C41.4107 (14)N4'—C4'1.4169 (15)
C4—C51.4503 (16)C4'—C5'1.4452 (16)
C5—C61.3632 (16)C5'—C6'1.3688 (17)
C7—C81.382 (2)C7'—C8'1.3898 (19)
C7—C121.414 (2)C7'—C12'1.4090 (18)
C8—C91.395 (2)C8'—C9'1.388 (2)
C9—C101.402 (4)C9'—C10'1.397 (2)
C10—C111.362 (4)C10'—C11'1.378 (3)
C11—C121.399 (2)C11'—C12'1.395 (2)
C12—C131.440 (3)C12'—C13'1.445 (2)
C13—C181.4075 (19)C13'—C18'1.4041 (19)
C13—C141.410 (2)C13'—C14'1.406 (2)
C14—C151.377 (3)C14'—C15'1.378 (3)
C15—C161.388 (3)C15'—C16'1.392 (3)
C16—C171.388 (2)C16'—C17'1.387 (2)
C17—C181.391 (2)C17'—C18'1.393 (2)
C19—C201.3894 (19)C19'—C20'1.3925 (17)
C19—C241.4080 (17)C19'—C24'1.4106 (16)
C20—C211.389 (2)C20'—C21'1.3890 (19)
C21—C221.396 (2)C21'—C22'1.394 (2)
C22—C231.376 (2)C22'—C23'1.381 (2)
C23—C241.3933 (18)C23'—C24'1.3944 (17)
C24—C251.4394 (18)C24'—C25'1.4395 (17)
C25—C261.3931 (18)C25'—C26'1.3947 (17)
C25—C301.4033 (16)C25'—C30'1.4051 (17)
C26—C271.382 (2)C26'—C27'1.382 (2)
C27—C281.398 (2)C27'—C28'1.395 (3)
C28—C291.3877 (19)C28'—C29'1.384 (2)
C29—C301.3875 (18)C29'—C30'1.3912 (17)
N1—S1—N2101.58 (6)N1'—S1'—N2'101.38 (7)
C1—N1—S1105.58 (10)N1'—C1'—C6'125.96 (15)
N1—C1—C6126.12 (12)N1'—C1'—C2'113.50 (14)
N1—C1—C2113.77 (12)C6'—C1'—C2'120.52 (12)
C6—C1—C2120.06 (11)C1'—N1'—S1'106.00 (12)
N2—C2—C3126.17 (12)N2'—C2'—C3'126.38 (14)
N2—C2—C1113.26 (11)N2'—C2'—C1'113.23 (13)
C3—C2—C1120.55 (11)C3'—C2'—C1'120.37 (12)
C2—N2—S1105.80 (10)C2'—N2'—S1'105.89 (11)
C7—N3—C18108.81 (11)C7'—N3'—C18'108.27 (10)
C7—N3—C5122.86 (11)C7'—N3'—C5'125.13 (11)
C18—N3—C5127.14 (11)C18'—N3'—C5'125.03 (11)
C4—C3—C2118.65 (11)C4'—C3'—C2'118.43 (12)
C19—N4—C30107.94 (10)C30'—N4'—C19'108.39 (9)
C19—N4—C4126.27 (10)C30'—N4'—C4'124.67 (10)
C30—N4—C4125.68 (10)C19'—N4'—C4'126.44 (10)
C3—C4—N4120.04 (11)C3'—C4'—N4'119.71 (11)
C3—C4—C5120.36 (11)C3'—C4'—C5'121.03 (11)
N4—C4—C5119.59 (10)N4'—C4'—C5'119.26 (10)
C6—C5—N3118.40 (11)C6'—C5'—N3'118.99 (12)
C6—C5—C4121.42 (11)C6'—C5'—C4'121.08 (11)
N3—C5—C4120.01 (10)N3'—C5'—C4'119.93 (10)
C5—C6—C1118.79 (11)C5'—C6'—C1'118.49 (13)
C8—C7—N3128.78 (14)C8'—C7'—N3'128.94 (12)
C8—C7—C12122.97 (14)C8'—C7'—C12'122.23 (12)
N3—C7—C12108.23 (13)N3'—C7'—C12'108.79 (12)
C7—C8—C9116.68 (19)C9'—C8'—C7'117.35 (13)
C8—C9—C10121.1 (2)C8'—C9'—C10'121.17 (16)
C11—C10—C9121.46 (16)C11'—C10'—C9'121.09 (15)
C10—C11—C12119.32 (19)C10'—C11'—C12'119.15 (14)
C11—C12—C7118.47 (18)C11'—C12'—C7'119.00 (14)
C11—C12—C13134.15 (17)C11'—C12'—C13'134.04 (13)
C7—C12—C13107.37 (12)C7'—C12'—C13'106.91 (12)
C18—C13—C14118.56 (17)C18'—C13'—C14'118.71 (14)
C18—C13—C12106.97 (13)C18'—C13'—C12'107.22 (11)
C14—C13—C12134.41 (15)C14'—C13'—C12'134.07 (14)
C15—C14—C13119.50 (16)C15'—C14'—C13'119.17 (15)
C14—C15—C16120.77 (16)C14'—C15'—C16'121.00 (14)
C15—C16—C17121.48 (19)C17'—C16'—C15'121.44 (16)
C16—C17—C18117.77 (16)C16'—C17'—C18'117.32 (15)
C17—C18—N3129.55 (12)C17'—C18'—N3'128.97 (13)
C17—C18—C13121.85 (14)C17'—C18'—C13'122.33 (13)
N3—C18—C13108.52 (13)N3'—C18'—C13'108.68 (12)
C20—C19—N4130.04 (12)C20'—C19'—N4'129.84 (11)
C20—C19—C24121.34 (12)C20'—C19'—C24'121.60 (11)
N4—C19—C24108.60 (11)N4'—C19'—C24'108.55 (10)
C21—C20—C19117.32 (14)C21'—C20'—C19'117.13 (13)
C20—C21—C22121.82 (15)C20'—C21'—C22'121.90 (13)
C23—C22—C21120.55 (13)C23'—C22'—C21'120.78 (13)
C22—C23—C24118.90 (13)C22'—C23'—C24'118.75 (13)
C23—C24—C19120.06 (12)C23'—C24'—C19'119.85 (12)
C23—C24—C25132.61 (12)C23'—C24'—C25'133.09 (12)
C19—C24—C25107.33 (10)C19'—C24'—C25'107.06 (10)
C26—C25—C30119.70 (12)C26'—C25'—C30'119.43 (12)
C26—C25—C24133.13 (12)C26'—C25'—C24'133.38 (12)
C30—C25—C24107.14 (11)C30'—C25'—C24'107.17 (10)
C27—C26—C25118.95 (12)C27'—C26'—C25'118.83 (14)
C26—C27—C28120.68 (13)C26'—C27'—C28'120.93 (13)
C29—C28—C27121.21 (13)C29'—C28'—C27'121.46 (14)
C30—C29—C28117.68 (12)C28'—C29'—C30'117.37 (13)
C29—C30—C25121.63 (11)C29'—C30'—N4'129.21 (11)
C29—C30—N4129.37 (11)C29'—C30'—C25'121.96 (11)
C25—C30—N4108.88 (11)N4'—C30'—C25'108.78 (10)
N2—S1—N1—C10.31 (12)C6'—C1'—N1'—S1'178.50 (13)
S1—N1—C1—C6177.92 (12)C2'—C1'—N1'—S1'0.19 (16)
S1—N1—C1—C20.55 (15)N2'—S1'—N1'—C1'0.34 (13)
N1—C1—C2—N20.63 (17)N1'—C1'—C2'—N2'0.08 (18)
C6—C1—C2—N2178.18 (13)C6'—C1'—C2'—N2'178.85 (13)
N1—C1—C2—C3178.95 (12)N1'—C1'—C2'—C3'178.81 (13)
C6—C1—C2—C33.51 (19)C6'—C1'—C2'—C3'2.4 (2)
C3—C2—N2—S1178.57 (11)C3'—C2'—N2'—S1'178.95 (12)
C1—C2—N2—S10.37 (15)C1'—C2'—N2'—S1'0.31 (15)
N1—S1—N2—C20.04 (12)N1'—S1'—N2'—C2'0.38 (12)
N2—C2—C3—C4179.75 (13)N2'—C2'—C3'—C4'179.63 (13)
C1—C2—C3—C41.67 (19)C1'—C2'—C3'—C4'1.82 (19)
C2—C3—C4—N4179.21 (11)C2'—C3'—C4'—N4'178.77 (11)
C2—C3—C4—C52.11 (18)C2'—C3'—C4'—C5'0.62 (19)
C19—N4—C4—C348.44 (18)C30'—N4'—C4'—C3'114.22 (14)
C30—N4—C4—C3127.51 (13)C19'—N4'—C4'—C3'56.71 (17)
C19—N4—C4—C5130.24 (13)C30'—N4'—C4'—C5'65.19 (16)
C30—N4—C4—C553.81 (17)C19'—N4'—C4'—C5'123.89 (13)
C7—N3—C5—C6104.02 (14)C7'—N3'—C5'—C6'110.74 (15)
C18—N3—C5—C662.05 (17)C18'—N3'—C5'—C6'53.26 (18)
C7—N3—C5—C471.32 (16)C7'—N3'—C5'—C4'69.28 (17)
C18—N3—C5—C4122.61 (13)C18'—N3'—C5'—C4'126.72 (13)
C3—C4—C5—C64.30 (19)C3'—C4'—C5'—C6'2.62 (19)
N4—C4—C5—C6177.02 (12)N4'—C4'—C5'—C6'176.77 (12)
C3—C4—C5—N3170.90 (11)C3'—C4'—C5'—N3'177.40 (12)
N4—C4—C5—N37.78 (17)N4'—C4'—C5'—N3'3.21 (17)
N3—C5—C6—C1172.85 (12)N3'—C5'—C6'—C1'178.01 (12)
C4—C5—C6—C12.43 (19)C4'—C5'—C6'—C1'2.0 (2)
N1—C1—C6—C5178.60 (13)N1'—C1'—C6'—C5'179.06 (15)
C2—C1—C6—C51.4 (2)C2'—C1'—C6'—C5'0.5 (2)
C18—N3—C7—C8177.07 (13)C18'—N3'—C7'—C8'176.16 (13)
C5—N3—C7—C88.8 (2)C5'—N3'—C7'—C8'9.9 (2)
C18—N3—C7—C121.56 (14)C18'—N3'—C7'—C12'1.68 (14)
C5—N3—C7—C12169.87 (11)C5'—N3'—C7'—C12'167.94 (12)
N3—C7—C8—C9178.66 (14)N3'—C7'—C8'—C9'177.53 (13)
C12—C7—C8—C90.2 (2)C12'—C7'—C8'—C9'0.1 (2)
C7—C8—C9—C100.4 (2)C7'—C8'—C9'—C10'0.6 (2)
C8—C9—C10—C110.2 (3)C8'—C9'—C10'—C11'0.7 (3)
C9—C10—C11—C120.2 (3)C9'—C10'—C11'—C12'0.1 (3)
C10—C11—C12—C70.3 (2)C10'—C11'—C12'—C7'0.5 (2)
C10—C11—C12—C13178.98 (16)C10'—C11'—C12'—C13'177.82 (15)
C8—C7—C12—C110.1 (2)C8'—C7'—C12'—C11'0.6 (2)
N3—C7—C12—C11178.62 (12)N3'—C7'—C12'—C11'177.39 (12)
C8—C7—C12—C13179.12 (13)C8'—C7'—C12'—C13'178.59 (12)
N3—C7—C12—C130.39 (14)N3'—C7'—C12'—C13'0.57 (14)
C11—C12—C13—C18176.62 (15)C11'—C12'—C13'—C18'174.93 (15)
C7—C12—C13—C182.17 (14)C7'—C12'—C13'—C18'2.59 (14)
C11—C12—C13—C146.4 (3)C11'—C12'—C13'—C14'5.4 (3)
C7—C12—C13—C14174.77 (15)C7'—C12'—C13'—C14'177.12 (14)
C18—C13—C14—C150.1 (2)C18'—C13'—C14'—C15'2.0 (2)
C12—C13—C14—C15176.62 (15)C12'—C13'—C14'—C15'178.35 (14)
C13—C14—C15—C161.6 (2)C13'—C14'—C15'—C16'0.2 (2)
C14—C15—C16—C170.6 (3)C14'—C15'—C16'—C17'1.3 (2)
C15—C16—C17—C181.9 (2)C15'—C16'—C17'—C18'0.9 (2)
C16—C17—C18—N3172.72 (13)C16'—C17'—C18'—N3'177.21 (14)
C16—C17—C18—C133.4 (2)C16'—C17'—C18'—C13'1.0 (2)
C7—N3—C18—C17179.52 (13)C7'—N3'—C18'—C17'178.27 (14)
C5—N3—C18—C1712.8 (2)C5'—N3'—C18'—C17'12.0 (2)
C7—N3—C18—C132.96 (14)C7'—N3'—C18'—C13'3.34 (14)
C5—N3—C18—C13170.62 (11)C5'—N3'—C18'—C13'169.62 (12)
C14—C13—C18—C172.50 (19)C14'—C13'—C18'—C17'2.4 (2)
C12—C13—C18—C17179.98 (12)C12'—C13'—C18'—C17'177.83 (13)
C14—C13—C18—N3174.37 (12)C14'—C13'—C18'—N3'176.11 (12)
C12—C13—C18—N33.14 (14)C12'—C13'—C18'—N3'3.65 (14)
C30—N4—C19—C20178.68 (14)C30'—N4'—C19'—C20'178.97 (13)
C4—N4—C19—C202.1 (2)C4'—N4'—C19'—C20'6.8 (2)
C30—N4—C19—C242.85 (14)C30'—N4'—C19'—C24'2.27 (13)
C4—N4—C19—C24179.39 (11)C4'—N4'—C19'—C24'174.42 (11)
N4—C19—C20—C21179.47 (14)N4'—C19'—C20'—C21'178.58 (13)
C24—C19—C20—C211.2 (2)C24'—C19'—C20'—C21'0.03 (19)
C19—C20—C21—C220.7 (2)C19'—C20'—C21'—C22'0.1 (2)
C20—C21—C22—C230.4 (3)C20'—C21'—C22'—C23'0.0 (2)
C21—C22—C23—C241.1 (2)C21'—C22'—C23'—C24'0.3 (2)
C22—C23—C24—C190.6 (2)C22'—C23'—C24'—C19'0.4 (2)
C22—C23—C24—C25178.76 (14)C22'—C23'—C24'—C25'178.75 (14)
C20—C19—C24—C230.5 (2)C20'—C19'—C24'—C23'0.31 (19)
N4—C19—C24—C23179.16 (12)N4'—C19'—C24'—C23'178.57 (11)
C20—C19—C24—C25179.96 (13)C20'—C19'—C24'—C25'179.05 (11)
N4—C19—C24—C251.33 (14)N4'—C19'—C24'—C25'2.07 (13)
C23—C24—C25—C261.0 (2)C23'—C24'—C25'—C26'1.7 (2)
C19—C24—C25—C26178.41 (14)C19'—C24'—C25'—C26'177.59 (13)
C23—C24—C25—C30178.73 (14)C23'—C24'—C25'—C30'179.66 (14)
C19—C24—C25—C300.69 (14)C19'—C24'—C25'—C30'1.10 (13)
C30—C25—C26—C270.92 (19)C30'—C25'—C26'—C27'1.04 (19)
C24—C25—C26—C27176.57 (14)C24'—C25'—C26'—C27'177.52 (13)
C25—C26—C27—C281.6 (2)C25'—C26'—C27'—C28'0.2 (2)
C26—C27—C28—C291.1 (2)C26'—C27'—C28'—C29'0.5 (2)
C27—C28—C29—C302.1 (2)C27'—C28'—C29'—C30'0.3 (2)
C28—C29—C30—C254.68 (19)C28'—C29'—C30'—N4'178.05 (12)
C28—C29—C30—N4179.79 (12)C28'—C29'—C30'—C25'0.61 (19)
C26—C25—C30—C294.19 (18)C19'—N4'—C30'—C29'176.13 (12)
C24—C25—C30—C29173.90 (11)C4'—N4'—C30'—C29'3.8 (2)
C26—C25—C30—N4179.46 (11)C19'—N4'—C30'—C25'1.57 (13)
C24—C25—C30—N42.46 (13)C4'—N4'—C30'—C25'173.89 (11)
C19—N4—C30—C29172.68 (12)C26'—C25'—C30'—C29'1.28 (18)
C4—N4—C30—C293.9 (2)C24'—C25'—C30'—C29'177.63 (11)
C19—N4—C30—C253.30 (13)C26'—C25'—C30'—N4'179.18 (11)
C4—N4—C30—C25179.87 (11)C24'—C25'—C30'—N4'0.28 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1SA···N20.852.252.959 (2)140
Selected geometric parameters for experimental and calculated structures of DCBT top
X-rayOptimized experimental structureOptimized structure 1Optimized structure 2
Space groupP1P1C2C2
a (Å)8.368.0113.9413.52
b (Å)8.738.6410.3910.61
c (Å)8.868.759.328.61
α (°)104.4104.190.090.0
β (°)94.294.7125.8106.2
γ (°)112.3112.890.090.0
S1—N1, S1—N2 (Å)1.616, 1.6141.620, 1.6181.6191.619
N1—C1, N2—C2 (Å)1.347, 1.3501.351, 1.3501.3491.350
C1—C2 (Å)1.4331.4451.4431.444
C1—C6, C2—C3 (Å)1.421, 1.4171.413, 1.4131.4141.410
C3—C4, C5—C6 (Å)1.366, 1.3631.375,1.3761.3741.376
C4—C5 (Å)1.4521.4421.4451.443
C4—N4, C5—N3 (Å)1.415, 1.4151.411, 1.4081.4111.410
DFBT–Carbazole dihedral angle (°)67.3, 69.964.4, 66.763.364.6
 

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