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organic compounds
The reaction of cinnamoyl isothiocyanate and aniline gave a the title cyclized thiourea, C13H16N2S. There are two molecules in the asymmetric unit. The pyrimidine-2-thione moiety in each molecule is almost perpendicular to the phenyl group. The molecules are linked by two intermolecular N—HS hydrogen bonds to form a dimer.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031320/is6010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031320/is6010Isup2.hkl |
CCDC reference: 262443
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.164
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.70 Deg. C18B -C15 -C18A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
4,4,6-Trimethyl-1-phenyl-3,4-dihydropyrimidine-2(1H)-thione top
Crystal data top
C13H16N2S | Dx = 1.197 Mg m−3 |
Mr = 232.34 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 5295 reflections |
a = 10.0407 (16) Å | θ = 1.3–27.5° |
b = 17.007 (3) Å | µ = 0.23 mm−1 |
c = 30.197 (5) Å | T = 273 K |
V = 5156.6 (14) Å3 | Block, colourless |
Z = 16 | 0.47 × 0.46 × 0.33 mm |
F(000) = 1984 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5628 independent reflections |
Radiation source: fine-focus sealed tube | 4954 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.3° |
ω scans | h = −7→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −21→21 |
Tmin = 0.900, Tmax = 0.928 | l = −38→37 |
28481 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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0557P)2 + 4.7245P] where P = (Fo2 + 2Fc2)/3 |
5628 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.16028 (7) | 0.15425 (4) | 0.32540 (2) | 0.04685 (18) | |
S2 | 0.23318 (8) | −0.01002 (4) | 0.43608 (2) | 0.0529 (2) | |
N1 | 0.2502 (2) | 0.07233 (11) | 0.25578 (6) | 0.0395 (4) | |
N2 | 0.2718 (2) | 0.01450 (12) | 0.32435 (7) | 0.0482 (5) | |
H2A | 0.2739 | 0.0212 | 0.3526 | 0.058* | |
N3 | 0.2505 (2) | 0.08474 (12) | 0.50624 (6) | 0.0483 (5) | |
N4 | 0.2280 (3) | 0.14398 (12) | 0.43824 (7) | 0.0564 (6) | |
H4A | 0.2135 | 0.1382 | 0.4104 | 0.068* | |
C1 | 0.2305 (2) | 0.07550 (13) | 0.30067 (7) | 0.0374 (5) | |
C2 | 0.3148 (3) | 0.00640 (14) | 0.23591 (8) | 0.0433 (5) | |
C3 | 0.3464 (3) | −0.05509 (15) | 0.26025 (9) | 0.0504 (6) | |
H3A | 0.3914 | −0.0963 | 0.2466 | 0.060* | |
C4 | 0.3143 (3) | −0.06284 (14) | 0.30831 (8) | 0.0457 (6) | |
C5 | 0.3441 (3) | 0.01268 (18) | 0.18741 (9) | 0.0596 (8) | |
H5A | 0.3871 | −0.0346 | 0.1775 | 0.089* | |
H5B | 0.4015 | 0.0568 | 0.1822 | 0.089* | |
H5C | 0.2623 | 0.0198 | 0.1714 | 0.089* | |
C6 | 0.2020 (4) | −0.12108 (18) | 0.31554 (12) | 0.0726 (9) | |
H6A | 0.1255 | −0.1050 | 0.2987 | 0.109* | |
H6B | 0.1796 | −0.1227 | 0.3464 | 0.109* | |
H6C | 0.2299 | −0.1724 | 0.3060 | 0.109* | |
C7 | 0.4367 (4) | −0.0879 (2) | 0.33465 (11) | 0.0739 (9) | |
H7A | 0.5072 | −0.0506 | 0.3300 | 0.111* | |
H7B | 0.4651 | −0.1390 | 0.3250 | 0.111* | |
H7C | 0.4149 | −0.0898 | 0.3656 | 0.111* | |
C8 | 0.2046 (2) | 0.13685 (13) | 0.22849 (7) | 0.0383 (5) | |
C9 | 0.2890 (3) | 0.19901 (16) | 0.21940 (9) | 0.0515 (6) | |
H9A | 0.3754 | 0.1995 | 0.2304 | 0.062* | |
C10 | 0.2426 (3) | 0.26041 (16) | 0.19360 (10) | 0.0575 (7) | |
H10A | 0.2984 | 0.3024 | 0.1870 | 0.069* | |
C11 | 0.1140 (3) | 0.25947 (17) | 0.17767 (9) | 0.0549 (7) | |
H11A | 0.0825 | 0.3016 | 0.1611 | 0.066* | |
C12 | 0.0332 (3) | 0.19731 (18) | 0.18607 (9) | 0.0569 (7) | |
H12A | −0.0529 | 0.1965 | 0.1747 | 0.068* | |
C13 | 0.0783 (3) | 0.13516 (16) | 0.21151 (8) | 0.0472 (6) | |
H13A | 0.0231 | 0.0924 | 0.2171 | 0.057* | |
C14 | 0.2375 (3) | 0.07820 (14) | 0.46147 (8) | 0.0437 (5) | |
C15 | 0.2480 (4) | 0.15996 (17) | 0.52705 (9) | 0.0623 (8) | |
C16 | 0.2410 (4) | 0.22419 (17) | 0.50309 (10) | 0.0728 (10) | |
H16A | 0.2370 | 0.2720 | 0.5179 | 0.087* | |
C17 | 0.2390 (3) | 0.22582 (15) | 0.45389 (9) | 0.0539 (7) | |
C18A | 0.2790 (11) | 0.1606 (3) | 0.57667 (19) | 0.054 (2)* | 0.54 (2) |
H18A | 0.3737 | 0.1626 | 0.5809 | 0.081* | 0.54 (2) |
H18B | 0.2441 | 0.1138 | 0.5901 | 0.081* | 0.54 (2) |
H18C | 0.2387 | 0.2060 | 0.5901 | 0.081* | 0.54 (2) |
C18B | 0.2167 (14) | 0.1589 (4) | 0.5761 (2) | 0.057 (3)* | 0.46 (2) |
H18D | 0.1220 | 0.1570 | 0.5802 | 0.086* | 0.46 (2) |
H18E | 0.2515 | 0.2056 | 0.5897 | 0.086* | 0.46 (2) |
H18F | 0.2569 | 0.1135 | 0.5894 | 0.086* | 0.46 (2) |
C19 | 0.3644 (4) | 0.2625 (2) | 0.43479 (13) | 0.0826 (11) | |
H19A | 0.4410 | 0.2343 | 0.4453 | 0.124* | |
H19B | 0.3702 | 0.3165 | 0.4440 | 0.124* | |
H19C | 0.3613 | 0.2600 | 0.4031 | 0.124* | |
C20 | 0.1169 (4) | 0.2702 (2) | 0.43750 (14) | 0.0843 (11) | |
H20A | 0.0381 | 0.2467 | 0.4496 | 0.126* | |
H20B | 0.1135 | 0.2679 | 0.4058 | 0.126* | |
H20C | 0.1223 | 0.3241 | 0.4468 | 0.126* | |
C21 | 0.2586 (3) | 0.01563 (14) | 0.53352 (8) | 0.0455 (6) | |
C22 | 0.3805 (3) | −0.00947 (19) | 0.54794 (9) | 0.0620 (8) | |
H22A | 0.4576 | 0.0157 | 0.5384 | 0.074* | |
C23 | 0.3886 (5) | −0.0724 (2) | 0.57676 (11) | 0.0792 (11) | |
H23A | 0.4712 | −0.0898 | 0.5867 | 0.095* | |
C24 | 0.2755 (6) | −0.10867 (19) | 0.59061 (11) | 0.0857 (13) | |
H24A | 0.2810 | −0.1512 | 0.6099 | 0.103* | |
C25 | 0.1540 (5) | −0.0833 (2) | 0.57650 (10) | 0.0809 (12) | |
H25A | 0.0773 | −0.1084 | 0.5864 | 0.097* | |
C26 | 0.1438 (3) | −0.02033 (19) | 0.54756 (9) | 0.0616 (8) | |
H26A | 0.0610 | −0.0029 | 0.5379 | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0612 (4) | 0.0397 (3) | 0.0397 (3) | 0.0066 (3) | 0.0032 (3) | −0.0007 (2) |
S2 | 0.0858 (5) | 0.0359 (3) | 0.0370 (3) | 0.0037 (3) | 0.0017 (3) | −0.0013 (2) |
N1 | 0.0479 (11) | 0.0370 (9) | 0.0335 (9) | 0.0030 (8) | 0.0012 (8) | 0.0032 (8) |
N2 | 0.0712 (15) | 0.0397 (11) | 0.0339 (10) | 0.0024 (10) | 0.0019 (10) | 0.0046 (8) |
N3 | 0.0737 (15) | 0.0384 (10) | 0.0328 (10) | 0.0033 (10) | 0.0032 (10) | 0.0006 (8) |
N4 | 0.0991 (19) | 0.0363 (11) | 0.0339 (10) | 0.0073 (11) | −0.0015 (11) | 0.0008 (8) |
C1 | 0.0416 (12) | 0.0352 (11) | 0.0354 (11) | −0.0037 (9) | 0.0000 (9) | 0.0026 (9) |
C2 | 0.0494 (13) | 0.0400 (12) | 0.0404 (12) | 0.0006 (10) | 0.0029 (10) | −0.0025 (9) |
C3 | 0.0632 (17) | 0.0408 (12) | 0.0471 (14) | 0.0077 (12) | 0.0045 (12) | −0.0028 (10) |
C4 | 0.0565 (15) | 0.0352 (11) | 0.0453 (13) | 0.0042 (11) | 0.0015 (11) | 0.0066 (10) |
C5 | 0.081 (2) | 0.0575 (16) | 0.0408 (14) | 0.0145 (15) | 0.0096 (13) | −0.0015 (12) |
C6 | 0.087 (2) | 0.0501 (16) | 0.081 (2) | −0.0131 (16) | 0.0174 (18) | 0.0047 (15) |
C7 | 0.077 (2) | 0.081 (2) | 0.0644 (19) | 0.0267 (18) | −0.0065 (17) | 0.0089 (16) |
C8 | 0.0460 (12) | 0.0372 (11) | 0.0317 (10) | 0.0029 (10) | 0.0024 (9) | 0.0034 (9) |
C9 | 0.0521 (15) | 0.0509 (14) | 0.0515 (15) | −0.0073 (12) | −0.0062 (12) | 0.0080 (12) |
C10 | 0.0708 (18) | 0.0446 (14) | 0.0569 (16) | −0.0077 (13) | 0.0010 (14) | 0.0119 (12) |
C11 | 0.0683 (18) | 0.0524 (15) | 0.0442 (14) | 0.0166 (14) | 0.0066 (13) | 0.0119 (11) |
C12 | 0.0446 (14) | 0.0765 (19) | 0.0495 (15) | 0.0131 (14) | −0.0008 (12) | 0.0120 (14) |
C13 | 0.0436 (13) | 0.0543 (14) | 0.0438 (13) | −0.0028 (11) | 0.0028 (10) | 0.0055 (11) |
C14 | 0.0562 (14) | 0.0396 (12) | 0.0353 (11) | 0.0036 (11) | 0.0041 (10) | 0.0011 (9) |
C15 | 0.100 (2) | 0.0469 (15) | 0.0403 (13) | 0.0029 (15) | 0.0050 (15) | −0.0073 (11) |
C16 | 0.127 (3) | 0.0407 (14) | 0.0504 (16) | 0.0034 (17) | 0.0014 (18) | −0.0087 (13) |
C17 | 0.083 (2) | 0.0336 (12) | 0.0454 (14) | 0.0048 (12) | 0.0048 (13) | 0.0000 (10) |
C19 | 0.100 (3) | 0.065 (2) | 0.082 (2) | −0.008 (2) | 0.015 (2) | −0.0043 (18) |
C20 | 0.106 (3) | 0.0545 (18) | 0.092 (3) | 0.0233 (19) | −0.011 (2) | −0.0093 (17) |
C21 | 0.0628 (16) | 0.0430 (13) | 0.0307 (11) | 0.0032 (12) | 0.0009 (11) | 0.0006 (9) |
C22 | 0.0679 (19) | 0.0721 (19) | 0.0462 (15) | 0.0178 (16) | 0.0036 (14) | 0.0025 (13) |
C23 | 0.111 (3) | 0.076 (2) | 0.0504 (17) | 0.041 (2) | −0.0071 (19) | 0.0045 (16) |
C24 | 0.171 (4) | 0.0449 (16) | 0.0415 (16) | 0.008 (2) | −0.017 (2) | 0.0034 (13) |
C25 | 0.121 (3) | 0.078 (2) | 0.0436 (16) | −0.045 (2) | −0.0035 (18) | 0.0073 (15) |
C26 | 0.072 (2) | 0.0719 (19) | 0.0407 (14) | −0.0141 (16) | −0.0062 (13) | 0.0041 (13) |
Geometric parameters (Å, º) top
S1—C1 | 1.688 (2) | C11—C12 | 1.357 (4) |
S2—C14 | 1.685 (2) | C11—H11A | 0.9300 |
N1—C1 | 1.371 (3) | C12—C13 | 1.383 (4) |
N1—C2 | 1.427 (3) | C12—H12A | 0.9300 |
N1—C8 | 1.447 (3) | C13—H13A | 0.9300 |
N2—C1 | 1.327 (3) | C15—C16 | 1.312 (4) |
N2—C4 | 1.465 (3) | C15—C18B | 1.513 (8) |
N2—H2A | 0.8600 | C15—C18A | 1.530 (7) |
N3—C14 | 1.363 (3) | C16—C17 | 1.486 (4) |
N3—C15 | 1.426 (3) | C16—H16A | 0.9300 |
N3—C21 | 1.438 (3) | C17—C19 | 1.519 (5) |
N4—C14 | 1.324 (3) | C17—C20 | 1.522 (5) |
N4—C17 | 1.474 (3) | C18A—H18A | 0.9600 |
N4—H4A | 0.8600 | C18A—H18B | 0.9600 |
C2—C3 | 1.317 (3) | C18A—H18C | 0.9600 |
C2—C5 | 1.498 (3) | C18B—H18D | 0.9600 |
C3—C4 | 1.492 (4) | C18B—H18E | 0.9600 |
C3—H3A | 0.9300 | C18B—H18F | 0.9600 |
C4—C6 | 1.517 (4) | C19—H19A | 0.9600 |
C4—C7 | 1.524 (4) | C19—H19B | 0.9600 |
C5—H5A | 0.9600 | C19—H19C | 0.9600 |
C5—H5B | 0.9600 | C20—H20A | 0.9600 |
C5—H5C | 0.9600 | C20—H20B | 0.9600 |
C6—H6A | 0.9600 | C20—H20C | 0.9600 |
C6—H6B | 0.9600 | C21—C22 | 1.368 (4) |
C6—H6C | 0.9600 | C21—C26 | 1.372 (4) |
C7—H7A | 0.9600 | C22—C23 | 1.382 (4) |
C7—H7B | 0.9600 | C22—H22A | 0.9300 |
C7—H7C | 0.9600 | C23—C24 | 1.358 (6) |
C8—C13 | 1.368 (4) | C23—H23A | 0.9300 |
C8—C9 | 1.382 (3) | C24—C25 | 1.362 (6) |
C9—C10 | 1.383 (4) | C24—H24A | 0.9300 |
C9—H9A | 0.9300 | C25—C26 | 1.386 (5) |
C10—C11 | 1.378 (4) | C25—H25A | 0.9300 |
C10—H10A | 0.9300 | C26—H26A | 0.9300 |
C1—N1—C2 | 120.80 (19) | C12—C13—H13A | 120.1 |
C1—N1—C8 | 119.18 (19) | N4—C14—N3 | 117.6 (2) |
C2—N1—C8 | 120.02 (18) | N4—C14—S2 | 120.62 (18) |
C1—N2—C4 | 128.0 (2) | N3—C14—S2 | 121.76 (18) |
C1—N2—H2A | 116.0 | C16—C15—N3 | 120.3 (2) |
C4—N2—H2A | 116.0 | C16—C15—C18B | 122.6 (4) |
C14—N3—C15 | 120.6 (2) | N3—C15—C18B | 115.1 (3) |
C14—N3—C21 | 120.5 (2) | C16—C15—C18A | 123.0 (3) |
C15—N3—C21 | 118.8 (2) | N3—C15—C18A | 115.8 (3) |
C14—N4—C17 | 128.5 (2) | C18B—C15—C18A | 23.7 (3) |
C14—N4—H4A | 115.7 | C15—C16—C17 | 124.6 (3) |
C17—N4—H4A | 115.7 | C15—C16—H16A | 117.7 |
N2—C1—N1 | 117.2 (2) | C17—C16—H16A | 117.7 |
N2—C1—S1 | 120.86 (18) | N4—C17—C16 | 107.7 (2) |
N1—C1—S1 | 121.94 (17) | N4—C17—C19 | 109.2 (3) |
C3—C2—N1 | 119.9 (2) | C16—C17—C19 | 112.1 (3) |
C3—C2—C5 | 123.7 (2) | N4—C17—C20 | 107.7 (3) |
N1—C2—C5 | 116.4 (2) | C16—C17—C20 | 110.2 (3) |
C2—C3—C4 | 124.1 (2) | C19—C17—C20 | 109.9 (3) |
C2—C3—H3A | 117.9 | C15—C18A—H18A | 109.5 |
C4—C3—H3A | 117.9 | C15—C18A—H18B | 109.5 |
N2—C4—C3 | 107.75 (19) | H18A—C18A—H18B | 109.5 |
N2—C4—C6 | 108.8 (2) | C15—C18A—H18C | 109.5 |
C3—C4—C6 | 111.0 (2) | H18A—C18A—H18C | 109.5 |
N2—C4—C7 | 108.3 (2) | H18B—C18A—H18C | 109.5 |
C3—C4—C7 | 111.0 (2) | C15—C18B—H18D | 109.5 |
C6—C4—C7 | 110.0 (3) | C15—C18B—H18E | 109.5 |
C2—C5—H5A | 109.5 | H18D—C18B—H18E | 109.5 |
C2—C5—H5B | 109.5 | C15—C18B—H18F | 109.5 |
H5A—C5—H5B | 109.5 | H18D—C18B—H18F | 109.5 |
C2—C5—H5C | 109.5 | H18E—C18B—H18F | 109.5 |
H5A—C5—H5C | 109.5 | C17—C19—H19A | 109.5 |
H5B—C5—H5C | 109.5 | C17—C19—H19B | 109.5 |
C4—C6—H6A | 109.5 | H19A—C19—H19B | 109.5 |
C4—C6—H6B | 109.5 | C17—C19—H19C | 109.5 |
H6A—C6—H6B | 109.5 | H19A—C19—H19C | 109.5 |
C4—C6—H6C | 109.5 | H19B—C19—H19C | 109.5 |
H6A—C6—H6C | 109.5 | C17—C20—H20A | 109.5 |
H6B—C6—H6C | 109.5 | C17—C20—H20B | 109.5 |
C4—C7—H7A | 109.5 | H20A—C20—H20B | 109.5 |
C4—C7—H7B | 109.5 | C17—C20—H20C | 109.5 |
H7A—C7—H7B | 109.5 | H20A—C20—H20C | 109.5 |
C4—C7—H7C | 109.5 | H20B—C20—H20C | 109.5 |
H7A—C7—H7C | 109.5 | C22—C21—C26 | 121.0 (3) |
H7B—C7—H7C | 109.5 | C22—C21—N3 | 119.2 (3) |
C13—C8—C9 | 120.7 (2) | C26—C21—N3 | 119.6 (3) |
C13—C8—N1 | 119.4 (2) | C21—C22—C23 | 119.7 (3) |
C9—C8—N1 | 119.9 (2) | C21—C22—H22A | 120.2 |
C8—C9—C10 | 118.9 (3) | C23—C22—H22A | 120.2 |
C8—C9—H9A | 120.6 | C24—C23—C22 | 119.8 (4) |
C10—C9—H9A | 120.6 | C24—C23—H23A | 120.1 |
C11—C10—C9 | 120.2 (3) | C22—C23—H23A | 120.1 |
C11—C10—H10A | 119.9 | C23—C24—C25 | 120.6 (3) |
C9—C10—H10A | 119.9 | C23—C24—H24A | 119.7 |
C12—C11—C10 | 120.3 (2) | C25—C24—H24A | 119.7 |
C12—C11—H11A | 119.8 | C24—C25—C26 | 120.5 (3) |
C10—C11—H11A | 119.8 | C24—C25—H25A | 119.7 |
C11—C12—C13 | 120.2 (3) | C26—C25—H25A | 119.7 |
C11—C12—H12A | 119.9 | C21—C26—C25 | 118.5 (3) |
C13—C12—H12A | 119.9 | C21—C26—H26A | 120.7 |
C8—C13—C12 | 119.7 (2) | C25—C26—H26A | 120.7 |
C8—C13—H13A | 120.1 | ||
C4—N2—C1—N1 | −12.3 (4) | C15—N3—C14—N4 | 2.6 (4) |
C4—N2—C1—S1 | 169.2 (2) | C21—N3—C14—N4 | 178.7 (3) |
C2—N1—C1—N2 | −1.1 (3) | C15—N3—C14—S2 | −177.2 (2) |
C8—N1—C1—N2 | 178.9 (2) | C21—N3—C14—S2 | −1.1 (4) |
C2—N1—C1—S1 | 177.42 (18) | C14—N3—C15—C16 | −4.0 (5) |
C8—N1—C1—S1 | −2.6 (3) | C21—N3—C15—C16 | 179.8 (3) |
C1—N1—C2—C3 | 5.5 (4) | C14—N3—C15—C18B | 160.3 (6) |
C8—N1—C2—C3 | −174.4 (2) | C21—N3—C15—C18B | −15.9 (7) |
C1—N1—C2—C5 | −173.8 (2) | C14—N3—C15—C18A | −173.4 (5) |
C8—N1—C2—C5 | 6.3 (3) | C21—N3—C15—C18A | 10.4 (6) |
N1—C2—C3—C4 | 2.5 (4) | N3—C15—C16—C17 | −1.8 (6) |
C5—C2—C3—C4 | −178.3 (3) | C18B—C15—C16—C17 | −164.9 (7) |
C1—N2—C4—C3 | 18.2 (4) | C18A—C15—C16—C17 | 166.8 (6) |
C1—N2—C4—C6 | −102.2 (3) | C14—N4—C17—C16 | −9.3 (4) |
C1—N2—C4—C7 | 138.3 (3) | C14—N4—C17—C19 | 112.6 (4) |
C2—C3—C4—N2 | −12.5 (4) | C14—N4—C17—C20 | −128.1 (3) |
C2—C3—C4—C6 | 106.5 (3) | C15—C16—C17—N4 | 7.4 (5) |
C2—C3—C4—C7 | −130.9 (3) | C15—C16—C17—C19 | −112.6 (4) |
C1—N1—C8—C13 | −89.9 (3) | C15—C16—C17—C20 | 124.7 (4) |
C2—N1—C8—C13 | 90.1 (3) | C14—N3—C21—C22 | 99.8 (3) |
C1—N1—C8—C9 | 90.9 (3) | C15—N3—C21—C22 | −84.0 (3) |
C2—N1—C8—C9 | −89.2 (3) | C14—N3—C21—C26 | −85.3 (3) |
C13—C8—C9—C10 | 1.4 (4) | C15—N3—C21—C26 | 90.8 (3) |
N1—C8—C9—C10 | −179.3 (2) | C26—C21—C22—C23 | 0.6 (4) |
C8—C9—C10—C11 | 0.5 (4) | N3—C21—C22—C23 | 175.3 (3) |
C9—C10—C11—C12 | −1.9 (4) | C21—C22—C23—C24 | −0.1 (5) |
C10—C11—C12—C13 | 1.4 (4) | C22—C23—C24—C25 | −0.4 (5) |
C9—C8—C13—C12 | −1.9 (4) | C23—C24—C25—C26 | 0.4 (5) |
N1—C8—C13—C12 | 178.8 (2) | C22—C21—C26—C25 | −0.5 (4) |
C11—C12—C13—C8 | 0.5 (4) | N3—C21—C26—C25 | −175.3 (3) |
C17—N4—C14—N3 | 4.8 (5) | C24—C25—C26—C21 | 0.0 (5) |
C17—N4—C14—S2 | −175.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···S2 | 0.86 | 2.61 | 3.422 (2) | 158 |
N4—H4A···S1 | 0.86 | 2.64 | 3.479 (2) | 167 |
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