Buy article online - an online subscription or single-article purchase is required to access this article.
There are two independent molecules in the asymmetric unit of the title compound, C
21H
18N
6S. The molecules are linked by C—H
S and C—H
N intermolecular and π–π stacking interactions.
Supporting information
CCDC reference: 642902
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.045
- wR factor = 0.055
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H16 .. S4 .. 3.45 Ang.
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S4
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S5
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S6
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S3
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. N10 .. 2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. S4 .. 3.23 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24 .. S1 .. 2.98 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16 .. S4 .. 4.26 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 6608
Count of symmetry unique reflns 3715
Completeness (_total/calc) 177.87%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2893
Fraction of Friedel pairs measured 0.779
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
2,4,6-tris(pyridin-2-ylsulfanyl)-1,3,5-triazine
top
Crystal data top
C18H12N6S3 | F(000) = 1680 |
Mr = 408.52 | Dx = 1.441 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6733 reflections |
a = 10.2018 (7) Å | θ = 2.2–31.3° |
b = 16.7019 (11) Å | µ = 0.41 mm−1 |
c = 22.1016 (14) Å | T = 298 K |
V = 3765.9 (4) Å3 | Prism, colourless |
Z = 8 | 0.39 × 0.08 × 0.02 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3651 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.082 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −12→12 |
30823 measured reflections | k = −19→19 |
6608 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.055 | w = 1/[σ2(Fo2) + (0.0112P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max = 0.001 |
6608 reflections | Δρmax = 0.37 e Å−3 |
579 parameters | Δρmin = −0.19 e Å−3 |
402 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (5) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.66448 (9) | 1.08458 (6) | 1.02430 (5) | 0.0622 (3) | |
S2 | 0.69358 (11) | 0.87064 (6) | 0.84847 (5) | 0.0756 (4) | |
S3 | 0.35688 (11) | 0.84304 (6) | 1.03282 (5) | 0.0764 (4) | |
N1 | 0.5185 (3) | 0.96146 (17) | 1.01683 (12) | 0.0521 (8) | |
N2 | 0.6679 (3) | 0.97323 (16) | 0.93498 (13) | 0.0490 (8) | |
N3 | 0.5252 (3) | 0.85927 (16) | 0.94098 (14) | 0.0511 (8) | |
N4 | 0.8490 (3) | 1.18454 (17) | 1.02521 (13) | 0.0600 (9) | |
N5 | 0.6671 (3) | 0.7139 (2) | 0.84360 (16) | 0.0847 (12) | |
N6 | 0.2405 (4) | 0.7470 (2) | 0.95585 (18) | 0.0816 (11) | |
C1 | 0.6145 (3) | 0.9973 (2) | 0.98621 (17) | 0.0456 (10) | |
C2 | 0.6186 (3) | 0.9026 (2) | 0.91523 (15) | 0.0496 (10) | |
C3 | 0.4795 (3) | 0.8922 (2) | 0.99140 (17) | 0.0512 (10) | |
C4 | 0.8112 (3) | 1.1221 (2) | 0.99236 (17) | 0.0500 (10) | |
C5 | 0.9624 (4) | 1.2202 (2) | 1.00947 (19) | 0.0672 (13) | |
H5 | 0.9900 | 1.2641 | 1.0321 | 0.081* | |
C6 | 1.0397 (4) | 1.1958 (2) | 0.9620 (2) | 0.0673 (12) | |
H6 | 1.1179 | 1.2217 | 0.9530 | 0.081* | |
C7 | 0.9977 (4) | 1.1321 (3) | 0.92842 (19) | 0.0822 (14) | |
H7 | 1.0468 | 1.1141 | 0.8957 | 0.099* | |
C8 | 0.8823 (4) | 1.0950 (2) | 0.94357 (17) | 0.0703 (12) | |
H8 | 0.8523 | 1.0518 | 0.9210 | 0.084* | |
C9 | 0.6037 (4) | 0.7817 (2) | 0.83222 (17) | 0.0555 (11) | |
C10 | 0.6019 (5) | 0.6463 (3) | 0.8296 (2) | 0.1054 (18) | |
H10 | 0.6426 | 0.5974 | 0.8371 | 0.126* | |
C11 | 0.4796 (6) | 0.6458 (3) | 0.8050 (2) | 0.0888 (17) | |
H11 | 0.4384 | 0.5977 | 0.7957 | 0.107* | |
C12 | 0.4190 (5) | 0.7163 (3) | 0.79453 (19) | 0.0919 (15) | |
H12 | 0.3352 | 0.7177 | 0.7780 | 0.110* | |
C13 | 0.4829 (4) | 0.7855 (2) | 0.80860 (18) | 0.0724 (13) | |
H13 | 0.4431 | 0.8348 | 0.8019 | 0.087* | |
C14 | 0.3430 (5) | 0.7519 (3) | 0.99206 (19) | 0.0652 (12) | |
C15 | 0.2254 (5) | 0.6773 (4) | 0.9259 (2) | 0.0963 (17) | |
H15 | 0.1533 | 0.6717 | 0.9005 | 0.116* | |
C16 | 0.3104 (6) | 0.6148 (3) | 0.9309 (2) | 0.0992 (19) | |
H16 | 0.2965 | 0.5681 | 0.9089 | 0.119* | |
C17 | 0.4140 (5) | 0.6208 (3) | 0.9678 (2) | 0.1011 (17) | |
H17 | 0.4727 | 0.5786 | 0.9720 | 0.121* | |
C18 | 0.4317 (4) | 0.6916 (3) | 0.9996 (2) | 0.0874 (15) | |
H18 | 0.5027 | 0.6978 | 1.0256 | 0.105* | |
S4 | 0.43380 (10) | 0.41028 (6) | 0.83088 (5) | 0.0754 (3) | |
S5 | 0.43065 (10) | 0.09853 (6) | 0.85965 (5) | 0.0733 (3) | |
S6 | 0.02308 (10) | 0.25983 (7) | 0.76507 (5) | 0.0850 (4) | |
N7 | 0.2383 (3) | 0.32149 (18) | 0.80228 (13) | 0.0561 (9) | |
N8 | 0.4200 (3) | 0.24996 (19) | 0.84198 (12) | 0.0517 (8) | |
N9 | 0.2262 (3) | 0.17960 (17) | 0.81236 (13) | 0.0509 (8) | |
N10 | 0.6030 (3) | 0.45151 (19) | 0.91112 (18) | 0.0793 (11) | |
C19 | 0.3584 (4) | 0.3164 (2) | 0.82505 (16) | 0.0537 (10) | |
C20 | 0.3471 (4) | 0.1838 (2) | 0.83490 (16) | 0.0482 (10) | |
C21 | 0.1795 (3) | 0.2514 (3) | 0.79641 (15) | 0.0517 (10) | |
C22 | 0.5828 (4) | 0.3956 (2) | 0.87041 (18) | 0.0565 (11) | |
C23 | 0.7145 (5) | 0.4458 (3) | 0.9417 (2) | 0.1017 (18) | |
H23 | 0.7324 | 0.4852 | 0.9702 | 0.122* | |
C24 | 0.8044 (5) | 0.3865 (3) | 0.9344 (3) | 0.1009 (18) | |
H24 | 0.8791 | 0.3850 | 0.9585 | 0.121* | |
C25 | 0.7845 (4) | 0.3304 (3) | 0.8921 (2) | 0.0878 (15) | |
H25 | 0.8451 | 0.2897 | 0.8855 | 0.105* | |
C26 | 0.6712 (4) | 0.3353 (2) | 0.85875 (19) | 0.0732 (12) | |
H26 | 0.6543 | 0.2981 | 0.8285 | 0.088* | |
C27 | 0.3125 (4) | 0.02178 (19) | 0.85014 (18) | 0.0628 (11) | |
N11 | 0.2841 (7) | −0.0156 (4) | 0.9021 (2) | 0.0732 (17) | 0.713 (12) |
C28 | 0.1976 (9) | −0.0758 (4) | 0.8970 (3) | 0.087 (2) | 0.713 (12) |
H28 | 0.1715 | −0.1012 | 0.9324 | 0.105* | 0.713 (12) |
C29 | 0.1449 (7) | −0.1027 (4) | 0.8443 (3) | 0.086 (2) | 0.713 (12) |
H29 | 0.0898 | −0.1470 | 0.8437 | 0.103* | 0.713 (12) |
C30 | 0.1764 (8) | −0.0615 (4) | 0.7912 (3) | 0.085 (2) | 0.713 (12) |
H30 | 0.1378 | −0.0753 | 0.7545 | 0.102* | 0.713 (12) |
C31 | 0.2661 (8) | −0.0001 (4) | 0.7946 (2) | 0.0760 (19) | 0.713 (12) |
H31 | 0.2944 | 0.0259 | 0.7598 | 0.091* | 0.713 (12) |
N11A | 0.2320 (14) | 0.0089 (8) | 0.8970 (5) | 0.076 (2) | 0.287 (12) |
C28A | 0.1375 (14) | −0.0463 (9) | 0.8874 (7) | 0.082 (2) | 0.287 (12) |
H28A | 0.0816 | −0.0581 | 0.9194 | 0.098* | 0.287 (12) |
C29A | 0.1181 (15) | −0.0859 (10) | 0.8343 (8) | 0.085 (3) | 0.287 (12) |
H29A | 0.0422 | −0.1152 | 0.8272 | 0.102* | 0.287 (12) |
C30A | 0.2177 (16) | −0.0804 (10) | 0.7910 (7) | 0.084 (3) | 0.287 (12) |
H30A | 0.2230 | −0.1168 | 0.7592 | 0.101* | 0.287 (12) |
C31A | 0.3080 (15) | −0.0193 (9) | 0.7969 (5) | 0.074 (3) | 0.287 (12) |
H31A | 0.3644 | −0.0065 | 0.7652 | 0.088* | 0.287 (12) |
C32 | −0.0228 (4) | 0.1608 (2) | 0.7477 (2) | 0.0698 (11) | |
N12 | −0.1250 (13) | 0.1448 (7) | 0.7840 (6) | 0.089 (2) | 0.513 (16) |
C33 | −0.1728 (11) | 0.0700 (7) | 0.7766 (6) | 0.091 (2) | 0.513 (16) |
H33 | −0.2386 | 0.0534 | 0.8029 | 0.109* | 0.513 (16) |
C34 | −0.1325 (13) | 0.0166 (5) | 0.7337 (7) | 0.084 (2) | 0.513 (16) |
H34 | −0.1675 | −0.0347 | 0.7320 | 0.100* | 0.513 (16) |
C35 | −0.0372 (13) | 0.0412 (5) | 0.6924 (5) | 0.084 (2) | 0.513 (16) |
H35 | −0.0124 | 0.0086 | 0.6603 | 0.101* | 0.513 (16) |
C36 | 0.0189 (16) | 0.1156 (7) | 0.7008 (7) | 0.078 (2) | 0.513 (16) |
H36 | 0.0839 | 0.1341 | 0.6749 | 0.093* | 0.513 (16) |
N12A | −0.1134 (14) | 0.1201 (7) | 0.7793 (6) | 0.092 (2) | 0.487 (16) |
C33A | −0.1484 (15) | 0.0492 (7) | 0.7552 (7) | 0.095 (2) | 0.487 (16) |
H33A | −0.2185 | 0.0226 | 0.7731 | 0.115* | 0.487 (16) |
C34A | −0.0906 (13) | 0.0130 (5) | 0.7072 (7) | 0.083 (3) | 0.487 (16) |
H34A | −0.1179 | −0.0370 | 0.6936 | 0.100* | 0.487 (16) |
C35A | 0.0114 (13) | 0.0540 (6) | 0.6789 (5) | 0.079 (2) | 0.487 (16) |
H35A | 0.0552 | 0.0316 | 0.6461 | 0.095* | 0.487 (16) |
C36A | 0.0462 (17) | 0.1284 (8) | 0.7006 (7) | 0.075 (2) | 0.487 (16) |
H36A | 0.1158 | 0.1563 | 0.6835 | 0.090* | 0.487 (16) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0570 (7) | 0.0494 (6) | 0.0803 (8) | −0.0088 (6) | 0.0111 (6) | −0.0195 (6) |
S2 | 0.0882 (9) | 0.0669 (8) | 0.0717 (8) | −0.0294 (7) | 0.0265 (7) | −0.0196 (6) |
S3 | 0.0755 (8) | 0.0610 (7) | 0.0929 (9) | −0.0218 (6) | 0.0314 (7) | −0.0159 (7) |
N1 | 0.051 (2) | 0.048 (2) | 0.057 (2) | −0.0010 (17) | 0.0082 (18) | −0.0116 (18) |
N2 | 0.057 (2) | 0.0364 (18) | 0.054 (2) | −0.0047 (16) | 0.0033 (18) | −0.0010 (16) |
N3 | 0.054 (2) | 0.0438 (19) | 0.056 (2) | −0.0076 (17) | 0.0059 (17) | −0.0053 (17) |
N4 | 0.063 (2) | 0.045 (2) | 0.072 (2) | −0.0124 (18) | 0.003 (2) | −0.0112 (19) |
N5 | 0.088 (3) | 0.062 (2) | 0.104 (3) | −0.002 (2) | 0.005 (2) | 0.007 (3) |
N6 | 0.076 (3) | 0.064 (3) | 0.105 (3) | −0.018 (2) | 0.012 (2) | −0.015 (3) |
C1 | 0.039 (2) | 0.042 (2) | 0.055 (3) | 0.0035 (19) | 0.007 (2) | −0.001 (2) |
C2 | 0.056 (3) | 0.041 (2) | 0.052 (3) | −0.006 (2) | −0.009 (2) | 0.002 (2) |
C3 | 0.055 (3) | 0.045 (3) | 0.053 (3) | −0.006 (2) | 0.000 (2) | −0.006 (2) |
C4 | 0.051 (3) | 0.040 (2) | 0.059 (3) | 0.003 (2) | −0.007 (2) | −0.001 (2) |
C5 | 0.077 (3) | 0.051 (3) | 0.073 (3) | −0.020 (3) | −0.008 (3) | 0.005 (2) |
C6 | 0.062 (3) | 0.067 (3) | 0.073 (3) | −0.007 (3) | 0.003 (3) | 0.001 (3) |
C7 | 0.070 (3) | 0.077 (3) | 0.099 (4) | −0.018 (3) | 0.021 (3) | −0.017 (3) |
C8 | 0.066 (3) | 0.065 (3) | 0.080 (3) | −0.025 (3) | 0.013 (3) | −0.027 (3) |
C9 | 0.064 (3) | 0.050 (3) | 0.052 (3) | −0.013 (2) | 0.016 (2) | −0.004 (2) |
C10 | 0.116 (5) | 0.062 (4) | 0.138 (5) | −0.001 (4) | 0.026 (4) | −0.004 (4) |
C11 | 0.130 (5) | 0.057 (4) | 0.079 (4) | −0.043 (4) | 0.012 (4) | −0.003 (3) |
C12 | 0.094 (4) | 0.101 (4) | 0.080 (3) | −0.040 (4) | −0.024 (3) | 0.016 (3) |
C13 | 0.075 (3) | 0.053 (3) | 0.089 (4) | −0.014 (3) | −0.008 (3) | 0.011 (3) |
C14 | 0.057 (3) | 0.059 (3) | 0.079 (3) | −0.020 (3) | 0.023 (3) | −0.001 (3) |
C15 | 0.079 (4) | 0.104 (4) | 0.105 (4) | −0.046 (4) | 0.020 (3) | −0.020 (4) |
C16 | 0.119 (5) | 0.064 (4) | 0.115 (5) | −0.038 (4) | 0.046 (4) | −0.020 (4) |
C17 | 0.115 (5) | 0.055 (4) | 0.134 (5) | −0.013 (3) | 0.023 (4) | −0.005 (3) |
C18 | 0.089 (4) | 0.052 (3) | 0.121 (4) | −0.010 (3) | 0.007 (3) | −0.005 (3) |
S4 | 0.0800 (8) | 0.0447 (6) | 0.1014 (9) | −0.0023 (6) | −0.0296 (7) | 0.0054 (7) |
S5 | 0.0735 (7) | 0.0528 (7) | 0.0935 (9) | 0.0073 (6) | −0.0247 (7) | 0.0156 (7) |
S6 | 0.0631 (7) | 0.0660 (8) | 0.1259 (11) | 0.0086 (7) | −0.0313 (7) | 0.0023 (7) |
N7 | 0.065 (2) | 0.043 (2) | 0.060 (2) | 0.0078 (19) | −0.0153 (19) | 0.0031 (18) |
N8 | 0.0596 (19) | 0.0445 (18) | 0.051 (2) | 0.0073 (19) | −0.0097 (17) | 0.0067 (18) |
N9 | 0.045 (2) | 0.046 (2) | 0.062 (2) | 0.0034 (17) | −0.0003 (17) | 0.0054 (17) |
N10 | 0.070 (3) | 0.052 (2) | 0.116 (3) | −0.008 (2) | −0.020 (3) | −0.008 (2) |
C19 | 0.064 (3) | 0.045 (3) | 0.051 (3) | −0.004 (2) | −0.012 (2) | 0.004 (2) |
C20 | 0.056 (3) | 0.045 (3) | 0.044 (2) | 0.007 (2) | 0.008 (2) | 0.003 (2) |
C21 | 0.056 (3) | 0.050 (2) | 0.049 (3) | 0.009 (3) | −0.003 (2) | −0.004 (2) |
C22 | 0.064 (3) | 0.040 (2) | 0.066 (3) | −0.013 (2) | −0.010 (2) | 0.004 (2) |
C23 | 0.086 (4) | 0.081 (4) | 0.138 (5) | −0.026 (3) | −0.040 (4) | −0.026 (3) |
C24 | 0.059 (3) | 0.083 (4) | 0.160 (6) | −0.011 (3) | −0.035 (4) | 0.009 (4) |
C25 | 0.055 (3) | 0.077 (4) | 0.131 (5) | −0.004 (3) | −0.015 (3) | −0.001 (3) |
C26 | 0.057 (3) | 0.072 (3) | 0.091 (3) | −0.007 (3) | 0.005 (3) | −0.016 (3) |
C27 | 0.082 (3) | 0.040 (2) | 0.067 (3) | 0.013 (2) | −0.018 (2) | 0.011 (2) |
N11 | 0.096 (4) | 0.049 (3) | 0.075 (3) | 0.003 (3) | −0.014 (3) | 0.014 (2) |
C28 | 0.113 (5) | 0.057 (4) | 0.091 (3) | −0.005 (3) | −0.015 (3) | 0.019 (3) |
C29 | 0.103 (4) | 0.049 (3) | 0.105 (4) | −0.006 (3) | −0.030 (3) | 0.013 (3) |
C30 | 0.107 (4) | 0.056 (4) | 0.090 (3) | 0.009 (3) | −0.040 (3) | 0.001 (3) |
C31 | 0.100 (4) | 0.055 (4) | 0.074 (3) | 0.005 (3) | −0.018 (3) | 0.014 (3) |
N11A | 0.099 (5) | 0.052 (5) | 0.076 (4) | 0.002 (4) | −0.009 (4) | 0.010 (4) |
C28A | 0.105 (5) | 0.054 (5) | 0.087 (4) | 0.000 (4) | −0.011 (4) | 0.016 (4) |
C29A | 0.106 (5) | 0.053 (5) | 0.097 (5) | −0.007 (4) | −0.022 (4) | 0.010 (4) |
C30A | 0.104 (5) | 0.055 (5) | 0.092 (4) | 0.006 (4) | −0.022 (4) | −0.006 (4) |
C31A | 0.098 (5) | 0.047 (5) | 0.077 (4) | 0.010 (5) | −0.013 (4) | 0.003 (4) |
C32 | 0.052 (3) | 0.067 (3) | 0.091 (3) | −0.009 (2) | −0.026 (2) | 0.016 (2) |
N12 | 0.073 (4) | 0.069 (5) | 0.125 (4) | −0.013 (4) | −0.009 (3) | 0.017 (4) |
C33 | 0.074 (5) | 0.072 (5) | 0.127 (5) | −0.014 (4) | −0.006 (4) | 0.010 (4) |
C34 | 0.072 (5) | 0.065 (4) | 0.114 (6) | −0.023 (4) | −0.011 (4) | 0.013 (4) |
C35 | 0.073 (6) | 0.069 (4) | 0.110 (5) | −0.039 (4) | −0.014 (4) | 0.005 (4) |
C36 | 0.068 (5) | 0.062 (4) | 0.103 (4) | −0.028 (4) | −0.020 (4) | 0.003 (4) |
N12A | 0.081 (4) | 0.073 (5) | 0.122 (4) | −0.016 (4) | −0.009 (3) | 0.023 (4) |
C33A | 0.083 (5) | 0.081 (5) | 0.122 (6) | −0.025 (4) | −0.007 (4) | 0.021 (4) |
C34A | 0.072 (6) | 0.066 (4) | 0.112 (6) | −0.040 (4) | −0.015 (4) | 0.020 (4) |
C35A | 0.070 (6) | 0.060 (4) | 0.107 (5) | −0.045 (4) | −0.016 (4) | 0.007 (4) |
C36A | 0.064 (5) | 0.060 (4) | 0.102 (4) | −0.032 (3) | −0.020 (4) | −0.001 (4) |
Geometric parameters (Å, º) top
S1—C1 | 1.759 (3) | N9—C20 | 1.332 (4) |
S1—C4 | 1.770 (4) | N9—C21 | 1.338 (4) |
S2—C2 | 1.746 (3) | N10—C22 | 1.313 (4) |
S2—C9 | 1.783 (4) | N10—C23 | 1.326 (5) |
S3—C3 | 1.754 (4) | C22—C26 | 1.377 (4) |
S3—C14 | 1.774 (4) | C23—C24 | 1.359 (5) |
N1—C1 | 1.333 (4) | C23—H23 | 0.9300 |
N1—C3 | 1.347 (4) | C24—C25 | 1.340 (5) |
N2—C1 | 1.319 (4) | C24—H24 | 0.9300 |
N2—C2 | 1.355 (4) | C25—C26 | 1.373 (5) |
N3—C2 | 1.325 (4) | C25—H25 | 0.9300 |
N3—C3 | 1.327 (4) | C26—H26 | 0.9300 |
N4—C4 | 1.327 (4) | C27—N11 | 1.340 (5) |
N4—C5 | 1.347 (4) | C27—N11A | 1.340 (7) |
N5—C9 | 1.328 (4) | C27—C31A | 1.364 (7) |
N5—C10 | 1.346 (5) | C27—C31 | 1.366 (5) |
N6—C14 | 1.319 (4) | N11—C28 | 1.344 (5) |
N6—C15 | 1.348 (5) | C28—C29 | 1.358 (5) |
C4—C8 | 1.376 (4) | C28—H28 | 0.9300 |
C5—C6 | 1.375 (5) | C29—C30 | 1.399 (6) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C6—C7 | 1.364 (4) | C30—C31 | 1.376 (5) |
C6—H6 | 0.9300 | C30—H30 | 0.9300 |
C7—C8 | 1.372 (5) | C31—H31 | 0.9300 |
C7—H7 | 0.9300 | N11A—C28A | 1.351 (7) |
C8—H8 | 0.9300 | C28A—C29A | 1.360 (8) |
C9—C13 | 1.340 (5) | C28A—H28A | 0.9300 |
C10—C11 | 1.360 (5) | C29A—C30A | 1.399 (8) |
C10—H10 | 0.9300 | C29A—H29A | 0.9300 |
C11—C12 | 1.351 (5) | C30A—C31A | 1.380 (7) |
C11—H11 | 0.9300 | C30A—H30A | 0.9300 |
C12—C13 | 1.363 (5) | C31A—H31A | 0.9300 |
C12—H12 | 0.9300 | C32—N12 | 1.342 (6) |
C13—H13 | 0.9300 | C32—N12A | 1.342 (6) |
C14—C18 | 1.365 (5) | C32—C36 | 1.350 (6) |
C15—C16 | 1.362 (6) | C32—C36A | 1.367 (6) |
C15—H15 | 0.9300 | N12—C33 | 1.352 (6) |
C16—C17 | 1.339 (6) | C33—C34 | 1.365 (7) |
C16—H16 | 0.9300 | C33—H33 | 0.9300 |
C17—C18 | 1.386 (5) | C34—C35 | 1.395 (7) |
C17—H17 | 0.9300 | C34—H34 | 0.9300 |
C18—H18 | 0.9300 | C35—C36 | 1.381 (6) |
S4—C19 | 1.751 (3) | C35—H35 | 0.9300 |
S4—C22 | 1.770 (4) | C36—H36 | 0.9300 |
S5—C20 | 1.747 (3) | N12A—C33A | 1.347 (7) |
S5—C27 | 1.772 (4) | C33A—C34A | 1.356 (7) |
S6—C21 | 1.746 (3) | C33A—H33A | 0.9300 |
S6—C32 | 1.762 (4) | C34A—C35A | 1.393 (7) |
N7—C21 | 1.321 (4) | C34A—H34A | 0.9300 |
N7—C19 | 1.327 (4) | C35A—C36A | 1.379 (6) |
N8—C19 | 1.330 (4) | C35A—H35A | 0.9300 |
N8—C20 | 1.342 (4) | C36A—H36A | 0.9300 |
| | | |
C1—S1—C4 | 110.37 (19) | N10—C22—C26 | 123.1 (4) |
C2—S2—C9 | 101.53 (18) | N10—C22—S4 | 112.0 (4) |
C3—S3—C14 | 101.14 (19) | C26—C22—S4 | 124.9 (4) |
C1—N1—C3 | 113.0 (3) | N10—C23—C24 | 124.8 (5) |
C1—N2—C2 | 112.9 (3) | N10—C23—H23 | 117.6 |
C2—N3—C3 | 112.8 (3) | C24—C23—H23 | 117.6 |
C4—N4—C5 | 117.1 (3) | C25—C24—C23 | 119.4 (5) |
C9—N5—C10 | 115.5 (4) | C25—C24—H24 | 120.3 |
C14—N6—C15 | 116.2 (4) | C23—C24—H24 | 120.3 |
N2—C1—N1 | 127.0 (3) | C24—C25—C26 | 117.4 (5) |
N2—C1—S1 | 122.9 (3) | C24—C25—H25 | 121.3 |
N1—C1—S1 | 110.0 (3) | C26—C25—H25 | 121.3 |
N3—C2—N2 | 127.2 (3) | C25—C26—C22 | 119.7 (4) |
N3—C2—S2 | 120.7 (3) | C25—C26—H26 | 120.1 |
N2—C2—S2 | 112.1 (3) | C22—C26—H26 | 120.1 |
N3—C3—N1 | 127.0 (3) | N11A—C27—C31A | 124.5 (6) |
N3—C3—S3 | 119.7 (3) | N11—C27—C31 | 124.8 (4) |
N1—C3—S3 | 113.3 (3) | N11—C27—S5 | 112.5 (3) |
N4—C4—C8 | 122.3 (3) | N11A—C27—S5 | 116.2 (5) |
N4—C4—S1 | 107.8 (3) | C31A—C27—S5 | 119.3 (5) |
C8—C4—S1 | 129.9 (3) | C31—C27—S5 | 122.4 (4) |
N4—C5—C6 | 123.9 (4) | C27—N11—C28 | 114.7 (4) |
N4—C5—H5 | 118.0 | N11—C28—C29 | 125.5 (5) |
C6—C5—H5 | 118.0 | N11—C28—H28 | 117.3 |
C7—C6—C5 | 117.8 (4) | C29—C28—H28 | 117.3 |
C7—C6—H6 | 121.1 | C28—C29—C30 | 117.8 (5) |
C5—C6—H6 | 121.1 | C28—C29—H29 | 121.1 |
C6—C7—C8 | 119.2 (4) | C30—C29—H29 | 121.1 |
C6—C7—H7 | 120.4 | C31—C30—C29 | 118.2 (5) |
C8—C7—H7 | 120.4 | C31—C30—H30 | 120.9 |
C7—C8—C4 | 119.7 (4) | C29—C30—H30 | 120.9 |
C7—C8—H8 | 120.2 | C27—C31—C30 | 118.7 (5) |
C4—C8—H8 | 120.2 | C27—C31—H31 | 120.7 |
N5—C9—C13 | 124.2 (4) | C30—C31—H31 | 120.7 |
N5—C9—S2 | 115.0 (4) | C27—N11A—C28A | 115.1 (6) |
C13—C9—S2 | 120.8 (4) | N11A—C28A—C29A | 124.9 (7) |
N5—C10—C11 | 123.3 (5) | N11A—C28A—H28A | 117.6 |
N5—C10—H10 | 118.3 | C29A—C28A—H28A | 117.6 |
C11—C10—H10 | 118.3 | C28A—C29A—C30A | 116.9 (7) |
C12—C11—C10 | 118.9 (5) | C28A—C29A—H29A | 121.5 |
C12—C11—H11 | 120.6 | C30A—C29A—H29A | 121.5 |
C10—C11—H11 | 120.6 | C31A—C30A—C29A | 117.9 (7) |
C11—C12—C13 | 118.8 (5) | C31A—C30A—H30A | 121.0 |
C11—C12—H12 | 120.6 | C29A—C30A—H30A | 121.0 |
C13—C12—H12 | 120.6 | C27—C31A—C30A | 118.4 (6) |
C9—C13—C12 | 119.2 (4) | C27—C31A—H31A | 120.8 |
C9—C13—H13 | 120.4 | C30A—C31A—H31A | 120.8 |
C12—C13—H13 | 120.4 | N12—C32—C36 | 126.3 (5) |
N6—C14—C18 | 123.6 (4) | N12A—C32—C36A | 123.4 (5) |
N6—C14—S3 | 115.1 (4) | N12—C32—S6 | 105.2 (5) |
C18—C14—S3 | 121.2 (4) | N12A—C32—S6 | 123.0 (6) |
N6—C15—C16 | 123.4 (5) | C36—C32—S6 | 127.5 (5) |
N6—C15—H15 | 118.3 | C36A—C32—S6 | 113.6 (5) |
C16—C15—H15 | 118.3 | C32—N12—C33 | 113.0 (5) |
C17—C16—C15 | 119.6 (6) | N12—C33—C34 | 125.4 (6) |
C17—C16—H16 | 120.2 | N12—C33—H33 | 117.3 |
C15—C16—H16 | 120.2 | C34—C33—H33 | 117.3 |
C16—C17—C18 | 118.4 (5) | C33—C34—C35 | 118.2 (6) |
C16—C17—H17 | 120.8 | C33—C34—H34 | 120.9 |
C18—C17—H17 | 120.8 | C35—C34—H34 | 120.9 |
C14—C18—C17 | 118.8 (5) | C36—C35—C34 | 117.7 (6) |
C14—C18—H18 | 120.6 | C36—C35—H35 | 121.1 |
C17—C18—H18 | 120.6 | C34—C35—H35 | 121.1 |
C19—S4—C22 | 106.85 (19) | C32—C36—C35 | 118.4 (6) |
C20—S5—C27 | 102.74 (18) | C32—C36—H36 | 120.8 |
C21—S6—C32 | 104.71 (19) | C35—C36—H36 | 120.8 |
C21—N7—C19 | 113.6 (3) | C32—N12A—C33A | 114.9 (6) |
C19—N8—C20 | 113.2 (3) | N12A—C33A—C34A | 125.9 (6) |
C20—N9—C21 | 112.4 (3) | N12A—C33A—H33A | 117.1 |
C22—N10—C23 | 115.6 (4) | C34A—C33A—H33A | 117.1 |
N7—C19—N8 | 126.6 (3) | C33A—C34A—C35A | 117.2 (6) |
N7—C19—S4 | 112.1 (3) | C33A—C34A—H34A | 121.4 |
N8—C19—S4 | 121.3 (3) | C35A—C34A—H34A | 121.4 |
N9—C20—N8 | 126.9 (3) | C36A—C35A—C34A | 118.6 (6) |
N9—C20—S5 | 121.8 (3) | C36A—C35A—H35A | 120.7 |
N8—C20—S5 | 111.4 (3) | C34A—C35A—H35A | 120.7 |
N7—C21—N9 | 127.4 (3) | C32—C36A—C35A | 119.2 (6) |
N7—C21—S6 | 112.5 (3) | C32—C36A—H36A | 120.4 |
N9—C21—S6 | 120.1 (3) | C35A—C36A—H36A | 120.4 |
| | | |
C2—N2—C1—N1 | −2.7 (5) | C23—N10—C22—C26 | −1.1 (6) |
C2—N2—C1—S1 | 177.0 (2) | C23—N10—C22—S4 | −178.4 (3) |
C3—N1—C1—N2 | 2.5 (5) | C19—S4—C22—N10 | −136.8 (3) |
C3—N1—C1—S1 | −177.3 (2) | C19—S4—C22—C26 | 45.9 (4) |
C4—S1—C1—N2 | −10.8 (3) | C22—N10—C23—C24 | −1.4 (7) |
C4—S1—C1—N1 | 168.9 (2) | N10—C23—C24—C25 | 2.6 (9) |
C3—N3—C2—N2 | 0.0 (5) | C23—C24—C25—C26 | −1.2 (7) |
C3—N3—C2—S2 | 179.8 (2) | C24—C25—C26—C22 | −1.1 (7) |
C1—N2—C2—N3 | 1.3 (5) | N10—C22—C26—C25 | 2.4 (6) |
C1—N2—C2—S2 | −178.5 (2) | S4—C22—C26—C25 | 179.3 (3) |
C9—S2—C2—N3 | 3.2 (3) | C20—S5—C27—N11 | −120.6 (5) |
C9—S2—C2—N2 | −176.9 (3) | C20—S5—C27—N11A | −88.5 (9) |
C2—N3—C3—N1 | −0.2 (5) | C20—S5—C27—C31A | 91.0 (10) |
C2—N3—C3—S3 | −179.0 (2) | C20—S5—C27—C31 | 64.8 (6) |
C1—N1—C3—N3 | −0.8 (5) | N11A—C27—N11—C28 | 77.9 (12) |
C1—N1—C3—S3 | 178.0 (2) | C31A—C27—N11—C28 | −30.1 (10) |
C14—S3—C3—N3 | 5.0 (4) | C31—C27—N11—C28 | −3.7 (8) |
C14—S3—C3—N1 | −174.0 (3) | S5—C27—N11—C28 | −178.2 (4) |
C5—N4—C4—C8 | −1.0 (5) | C27—N11—C28—C29 | 3.6 (9) |
C5—N4—C4—S1 | 177.7 (3) | N11—C28—C29—C30 | −4.2 (11) |
C1—S1—C4—N4 | −175.9 (2) | C28—C29—C30—C31 | 4.7 (10) |
C1—S1—C4—C8 | 2.7 (4) | N11—C27—C31—C30 | 4.7 (8) |
C4—N4—C5—C6 | −0.1 (6) | N11A—C27—C31—C30 | −28.1 (10) |
N4—C5—C6—C7 | 0.9 (6) | C31A—C27—C31—C30 | 89.5 (17) |
C5—C6—C7—C8 | −0.7 (6) | S5—C27—C31—C30 | 178.6 (4) |
C6—C7—C8—C4 | −0.4 (6) | C29—C30—C31—C27 | −4.9 (9) |
N4—C4—C8—C7 | 1.3 (6) | N11—C27—N11A—C28A | −94.3 (16) |
S1—C4—C8—C7 | −177.2 (3) | C31A—C27—N11A—C28A | −3.5 (18) |
C10—N5—C9—C13 | 0.2 (7) | C31—C27—N11A—C28A | 21.0 (15) |
C10—N5—C9—S2 | −177.8 (3) | S5—C27—N11A—C28A | 176.0 (9) |
C2—S2—C9—N5 | −105.0 (3) | C27—N11A—C28A—C29A | −2 (2) |
C2—S2—C9—C13 | 76.9 (4) | N11A—C28A—C29A—C30A | 13 (3) |
C9—N5—C10—C11 | 0.4 (7) | C28A—C29A—C30A—C31A | −18 (3) |
N5—C10—C11—C12 | −0.7 (8) | N11—C27—C31A—C30A | 32.1 (18) |
C10—C11—C12—C13 | 0.4 (7) | N11A—C27—C31A—C30A | −2 (2) |
N5—C9—C13—C12 | −0.5 (7) | C31—C27—C31A—C30A | −77.3 (18) |
S2—C9—C13—C12 | 177.4 (3) | S5—C27—C31A—C30A | 178.2 (11) |
C11—C12—C13—C9 | 0.2 (7) | C29A—C30A—C31A—C27 | 13 (3) |
C15—N6—C14—C18 | 0.6 (6) | C21—S6—C32—N12 | 114.8 (8) |
C15—N6—C14—S3 | −177.9 (3) | C21—S6—C32—N12A | 107.5 (11) |
C3—S3—C14—N6 | −102.7 (3) | C21—S6—C32—C36 | −76.2 (13) |
C3—S3—C14—C18 | 78.7 (4) | C21—S6—C32—C36A | −70.0 (11) |
C14—N6—C15—C16 | −1.0 (7) | N12A—C32—N12—C33 | −19 (4) |
N6—C15—C16—C17 | 0.9 (8) | C36—C32—N12—C33 | 11 (2) |
C15—C16—C17—C18 | −0.4 (8) | C36A—C32—N12—C33 | 7 (3) |
N6—C14—C18—C17 | −0.2 (7) | S6—C32—N12—C33 | −179.7 (11) |
S3—C14—C18—C17 | 178.2 (3) | C32—N12—C33—C34 | −6 (2) |
C16—C17—C18—C14 | 0.1 (7) | N12—C33—C34—C35 | −2.2 (18) |
C21—N7—C19—N8 | −0.6 (5) | C33—C34—C35—C36 | 5.7 (18) |
C21—N7—C19—S4 | 179.0 (3) | N12—C32—C36—C35 | −8 (2) |
C20—N8—C19—N7 | −1.0 (5) | N12A—C32—C36—C35 | 2 (2) |
C20—N8—C19—S4 | 179.4 (3) | C36A—C32—C36—C35 | 163 (9) |
C22—S4—C19—N7 | 172.7 (3) | S6—C32—C36—C35 | −174.8 (9) |
C22—S4—C19—N8 | −7.6 (4) | C34—C35—C36—C32 | −1 (2) |
C21—N9—C20—N8 | −0.2 (5) | N12—C32—N12A—C33A | 150 (6) |
C21—N9—C20—S5 | 179.6 (2) | C36—C32—N12A—C33A | −5 (2) |
C19—N8—C20—N9 | 1.5 (5) | C36A—C32—N12A—C33A | −11 (2) |
C19—N8—C20—S5 | −178.4 (3) | S6—C32—N12A—C33A | 171.9 (11) |
C27—S5—C20—N9 | −3.3 (3) | C32—N12A—C33A—C34A | 8 (3) |
C27—S5—C20—N8 | 176.6 (3) | N12A—C33A—C34A—C35A | −2 (2) |
C19—N7—C21—N9 | 2.2 (5) | C33A—C34A—C35A—C36A | −0.8 (17) |
C19—N7—C21—S6 | −178.9 (3) | N12—C32—C36A—C35A | −1 (3) |
C20—N9—C21—N7 | −1.8 (5) | N12A—C32—C36A—C35A | 8 (3) |
C20—N9—C21—S6 | 179.4 (2) | C36—C32—C36A—C35A | −13 (6) |
C32—S6—C21—N7 | 168.8 (3) | S6—C32—C36A—C35A | −174.0 (12) |
C32—S6—C21—N9 | −12.2 (3) | C34A—C35A—C36A—C32 | −2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···N6i | 0.93 | 2.63 | 3.457 (6) | 149 |
C17—H17···N10 | 0.93 | 2.84 | 3.644 (6) | 145 |
C11—H11···S4 | 0.93 | 3.23 | 4.002 (5) | 142 |
C16—H16···S4 | 0.93 | 3.45 | 4.259 (5) | 147 |
C24—H24···S1i | 0.93 | 2.98 | 3.816 (4) | 150 |
Symmetry code: (i) x+1/2, −y+3/2, −z+2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.