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The structure of the title molecule, C
38H
36N
2O
2S
4, is stabilized by intramolecular C—H
N hydrogen bond and π–π interactions. The molecular packing in the crystal is stabilized by C—H
O, C—H
S, and C—H
π interactions.
Supporting information
CCDC reference: 225859
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.126
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low .............. 24.97 Deg.
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.31
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
6,22-dioxaparazylenyl 2,10,18,26-tetrathia-33,35 diaza pentacyclo
(27.3.1.1
4,8.1
12,16.1
20,24)hexatriconta-4,6,8(36),12,14,16 (35),20,22,
24 (34),28,30,32-dodecaene
top
Crystal data top
C38H36N2O2S4 | Z = 2 |
Mr = 680.93 | F(000) = 716 |
Triclinic, P1 | Dx = 1.340 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2571 (10) Å | Cell parameters from 25 reflections |
b = 12.3622 (7) Å | θ = 19.7–28.2° |
c = 14.2374 (10) Å | µ = 0.32 mm−1 |
α = 94.326 (5)° | T = 293 K |
β = 108.527 (6)° | Block, colourless |
γ = 96.725 (6)° | 0.30 × 0.25 × 0.20 mm |
V = 1687.8 (2) Å3 | |
Data collection top
Enraf Nonius CAD-4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.5° |
Graphite monochromator | h = 0→12 |
ω–2θ scans | k = −14→14 |
6283 measured reflections | l = −16→16 |
5919 independent reflections | 3 standard reflections every 100 reflections |
3917 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.2974P] where P = (Fo2 + 2Fc2)/3 |
5919 reflections | (Δ/σ)max < 0.001 |
415 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.89295 (8) | 0.61289 (6) | 0.57529 (6) | 0.0524 (2) | |
S2 | 0.81574 (9) | 1.08627 (7) | 0.42413 (7) | 0.0716 (3) | |
S3 | 0.23490 (10) | 1.05935 (7) | 0.30174 (6) | 0.0633 (3) | |
S4 | 0.22972 (8) | 0.52566 (6) | 0.19901 (6) | 0.0494 (2) | |
N1 | 0.5429 (2) | 0.59062 (17) | 0.37910 (16) | 0.0401 (5) | |
C2 | 0.6105 (3) | 0.6070 (2) | 0.4770 (2) | 0.0426 (7) | |
C3 | 0.5839 (3) | 0.6858 (3) | 0.5396 (2) | 0.0556 (8) | |
H3 | 0.6309 | 0.6935 | 0.6080 | 0.067* | |
C4 | 0.4878 (3) | 0.7523 (3) | 0.5002 (3) | 0.0612 (9) | |
H4 | 0.4677 | 0.8054 | 0.5413 | 0.073* | |
C5 | 0.4212 (3) | 0.7392 (2) | 0.3983 (2) | 0.0523 (8) | |
H5 | 0.3581 | 0.7852 | 0.3694 | 0.063* | |
C6 | 0.4495 (3) | 0.6572 (2) | 0.3400 (2) | 0.0396 (6) | |
C7 | 0.7200 (3) | 0.5366 (2) | 0.5175 (2) | 0.0545 (8) | |
H7A | 0.7210 | 0.4843 | 0.4635 | 0.065* | |
H7B | 0.6954 | 0.4955 | 0.5663 | 0.065* | |
C8 | 0.9420 (3) | 0.6409 (3) | 0.4681 (2) | 0.0551 (8) | |
H8A | 1.0364 | 0.6796 | 0.4913 | 0.066* | |
H8B | 0.9424 | 0.5714 | 0.4317 | 0.066* | |
C9 | 0.8510 (3) | 0.7074 (2) | 0.3962 (2) | 0.0441 (7) | |
C10 | 0.8155 (3) | 0.8039 (2) | 0.4303 (2) | 0.0430 (7) | |
H10 | 0.8494 | 0.8290 | 0.4981 | 0.052* | |
C11 | 0.7304 (3) | 0.8633 (2) | 0.3649 (2) | 0.0445 (7) | |
C12 | 0.6828 (3) | 0.8269 (3) | 0.2628 (2) | 0.0496 (7) | |
H12 | 0.6253 | 0.8662 | 0.2181 | 0.060* | |
C13 | 0.7213 (3) | 0.7329 (3) | 0.2287 (2) | 0.0521 (8) | |
C14 | 0.8023 (3) | 0.6718 (3) | 0.2954 (2) | 0.0510 (7) | |
H14 | 0.8241 | 0.6063 | 0.2720 | 0.061* | |
C15 | 0.6889 (3) | 0.9648 (2) | 0.4051 (2) | 0.0541 (8) | |
H15A | 0.6752 | 0.9529 | 0.4681 | 0.065* | |
H15B | 0.6008 | 0.9771 | 0.3590 | 0.065* | |
C16 | 0.7757 (3) | 1.1239 (3) | 0.2991 (3) | 0.0587 (9) | |
H16A | 0.8532 | 1.1745 | 0.2955 | 0.070* | |
H16B | 0.7643 | 1.0587 | 0.2531 | 0.070* | |
C17 | 0.6468 (3) | 1.1760 (2) | 0.2673 (2) | 0.0424 (7) | |
C18 | 0.6523 (3) | 1.2880 (2) | 0.2726 (2) | 0.0517 (8) | |
H18 | 0.7375 | 1.3337 | 0.2943 | 0.062* | |
C19 | 0.5303 (4) | 1.3315 (2) | 0.2453 (2) | 0.0574 (8) | |
H19 | 0.5314 | 1.4070 | 0.2473 | 0.069* | |
C20 | 0.4071 (3) | 1.2615 (2) | 0.2150 (2) | 0.0524 (8) | |
H20 | 0.3231 | 1.2889 | 0.1960 | 0.063* | |
C21 | 0.4084 (3) | 1.1498 (2) | 0.21287 (19) | 0.0417 (7) | |
N22 | 0.5267 (2) | 1.10677 (18) | 0.23692 (17) | 0.0435 (6) | |
C23 | 0.2768 (3) | 1.0703 (3) | 0.1888 (2) | 0.0505 (7) | |
H23A | 0.2893 | 0.9991 | 0.1624 | 0.061* | |
H23B | 0.2018 | 1.0961 | 0.1390 | 0.061* | |
C24 | 0.0554 (3) | 0.9941 (3) | 0.2527 (3) | 0.0598 (9) | |
H24A | 0.0200 | 0.9845 | 0.3075 | 0.072* | |
H24B | 0.0004 | 1.0417 | 0.2103 | 0.072* | |
C25 | 0.0390 (3) | 0.8849 (2) | 0.1937 (2) | 0.0462 (7) | |
C26 | 0.0019 (3) | 0.8773 (2) | 0.0914 (2) | 0.0502 (8) | |
H26 | −0.0235 | 0.9380 | 0.0590 | 0.060* | |
C27 | 0.0020 (3) | 0.7806 (2) | 0.0362 (2) | 0.0472 (7) | |
C28 | 0.0337 (3) | 0.6886 (2) | 0.0827 (2) | 0.0462 (7) | |
H28 | 0.0313 | 0.6229 | 0.0453 | 0.055* | |
C29 | 0.0691 (3) | 0.6946 (2) | 0.1856 (2) | 0.0413 (7) | |
C30 | 0.0726 (3) | 0.7926 (2) | 0.2410 (2) | 0.0435 (7) | |
H30 | 0.0975 | 0.7967 | 0.3101 | 0.052* | |
C31 | 0.1078 (3) | 0.5950 (2) | 0.2382 (2) | 0.0486 (7) | |
H31A | 0.0238 | 0.5435 | 0.2267 | 0.058* | |
H31B | 0.1472 | 0.6179 | 0.3095 | 0.058* | |
C32 | 0.3765 (3) | 0.6343 (2) | 0.2305 (2) | 0.0463 (7) | |
H32A | 0.4415 | 0.6137 | 0.1980 | 0.056* | |
H32B | 0.3443 | 0.7006 | 0.2054 | 0.056* | |
O33 | 0.6836 (2) | 0.6900 (2) | 0.13039 (17) | 0.0800 (8) | |
C34 | 0.6355 (3) | 0.7603 (4) | 0.0554 (3) | 0.0841 (13) | |
H34A | 0.6703 | 0.7432 | 0.0010 | 0.101* | |
H34B | 0.6731 | 0.8358 | 0.0834 | 0.101* | |
C35 | 0.4792 (3) | 0.7492 (3) | 0.0149 (2) | 0.0628 (9) | |
C36 | 0.4121 (4) | 0.8385 (3) | 0.0059 (2) | 0.0684 (10) | |
H36 | 0.4634 | 0.9081 | 0.0285 | 0.082* | |
C37 | 0.2690 (3) | 0.8276 (3) | −0.0363 (2) | 0.0633 (9) | |
H37 | 0.2255 | 0.8899 | −0.0426 | 0.076* | |
C38 | 0.1899 (3) | 0.7251 (3) | −0.0691 (2) | 0.0518 (8) | |
C39 | 0.2581 (4) | 0.6353 (3) | −0.0584 (2) | 0.0630 (9) | |
H39 | 0.2072 | 0.5653 | −0.0785 | 0.076* | |
C40 | 0.4003 (4) | 0.6473 (3) | −0.0187 (3) | 0.0690 (10) | |
H40 | 0.4443 | 0.5853 | −0.0142 | 0.083* | |
C41 | 0.0344 (3) | 0.7126 (3) | −0.1143 (2) | 0.0610 (9) | |
H41A | 0.0107 | 0.7260 | −0.1836 | 0.073* | |
H41B | −0.0046 | 0.6376 | −0.1130 | 0.073* | |
O42 | −0.0275 (2) | 0.78483 (18) | −0.06458 (15) | 0.0605 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0489 (5) | 0.0507 (4) | 0.0492 (5) | 0.0125 (3) | 0.0011 (3) | 0.0135 (3) |
S2 | 0.0557 (5) | 0.0474 (5) | 0.0844 (7) | 0.0073 (4) | −0.0148 (4) | 0.0083 (4) |
S3 | 0.0701 (6) | 0.0603 (5) | 0.0530 (5) | −0.0075 (4) | 0.0199 (4) | −0.0041 (4) |
S4 | 0.0437 (4) | 0.0380 (4) | 0.0578 (5) | 0.0046 (3) | 0.0054 (3) | 0.0033 (3) |
N1 | 0.0370 (13) | 0.0354 (12) | 0.0446 (14) | 0.0007 (10) | 0.0103 (11) | 0.0050 (10) |
C2 | 0.0394 (15) | 0.0405 (15) | 0.0438 (17) | −0.0033 (12) | 0.0106 (13) | 0.0087 (13) |
C3 | 0.0507 (19) | 0.067 (2) | 0.0442 (18) | 0.0026 (16) | 0.0131 (15) | −0.0015 (15) |
C4 | 0.0508 (19) | 0.062 (2) | 0.065 (2) | 0.0052 (16) | 0.0195 (17) | −0.0193 (17) |
C5 | 0.0353 (16) | 0.0462 (17) | 0.071 (2) | 0.0088 (13) | 0.0117 (15) | −0.0002 (15) |
C6 | 0.0356 (15) | 0.0352 (15) | 0.0457 (16) | −0.0002 (12) | 0.0116 (12) | 0.0067 (12) |
C7 | 0.0575 (19) | 0.0458 (17) | 0.0536 (18) | 0.0063 (15) | 0.0076 (15) | 0.0158 (14) |
C8 | 0.0475 (18) | 0.0558 (19) | 0.066 (2) | 0.0192 (15) | 0.0181 (15) | 0.0159 (16) |
C9 | 0.0346 (15) | 0.0464 (17) | 0.0546 (18) | 0.0073 (13) | 0.0176 (13) | 0.0127 (14) |
C10 | 0.0361 (15) | 0.0442 (16) | 0.0453 (16) | 0.0049 (12) | 0.0072 (13) | 0.0135 (13) |
C11 | 0.0355 (15) | 0.0428 (16) | 0.0516 (18) | 0.0046 (12) | 0.0082 (13) | 0.0141 (13) |
C12 | 0.0335 (15) | 0.064 (2) | 0.0476 (18) | 0.0034 (14) | 0.0066 (13) | 0.0191 (15) |
C13 | 0.0309 (15) | 0.077 (2) | 0.0447 (18) | 0.0008 (15) | 0.0108 (13) | 0.0061 (16) |
C14 | 0.0381 (16) | 0.0596 (19) | 0.059 (2) | 0.0090 (14) | 0.0211 (14) | 0.0021 (15) |
C15 | 0.0494 (18) | 0.0485 (17) | 0.060 (2) | 0.0138 (14) | 0.0072 (15) | 0.0164 (15) |
C16 | 0.0398 (17) | 0.0468 (18) | 0.089 (2) | 0.0055 (14) | 0.0204 (16) | 0.0110 (17) |
C17 | 0.0424 (16) | 0.0408 (16) | 0.0470 (16) | 0.0090 (13) | 0.0166 (13) | 0.0105 (13) |
C18 | 0.061 (2) | 0.0396 (16) | 0.0551 (19) | 0.0030 (14) | 0.0202 (15) | 0.0085 (14) |
C19 | 0.082 (2) | 0.0380 (16) | 0.059 (2) | 0.0205 (17) | 0.0278 (18) | 0.0145 (15) |
C20 | 0.059 (2) | 0.0545 (19) | 0.0488 (18) | 0.0255 (16) | 0.0167 (15) | 0.0152 (14) |
C21 | 0.0445 (16) | 0.0475 (16) | 0.0320 (14) | 0.0144 (13) | 0.0083 (12) | 0.0068 (12) |
N22 | 0.0409 (13) | 0.0420 (13) | 0.0476 (14) | 0.0110 (11) | 0.0120 (11) | 0.0081 (11) |
C23 | 0.0425 (17) | 0.0604 (19) | 0.0445 (17) | 0.0149 (14) | 0.0070 (13) | 0.0030 (14) |
C24 | 0.060 (2) | 0.0534 (19) | 0.077 (2) | 0.0161 (16) | 0.0352 (18) | 0.0056 (17) |
C25 | 0.0304 (15) | 0.0481 (17) | 0.060 (2) | 0.0080 (12) | 0.0142 (13) | 0.0063 (14) |
C26 | 0.0374 (16) | 0.0459 (17) | 0.067 (2) | 0.0122 (13) | 0.0120 (14) | 0.0166 (15) |
C27 | 0.0310 (14) | 0.0561 (18) | 0.0474 (17) | 0.0053 (13) | 0.0023 (12) | 0.0118 (14) |
C28 | 0.0381 (15) | 0.0470 (17) | 0.0483 (18) | 0.0070 (13) | 0.0067 (13) | 0.0050 (14) |
C29 | 0.0289 (14) | 0.0416 (15) | 0.0525 (18) | 0.0014 (11) | 0.0122 (12) | 0.0107 (13) |
C30 | 0.0337 (15) | 0.0494 (17) | 0.0483 (17) | 0.0050 (12) | 0.0140 (13) | 0.0104 (14) |
C31 | 0.0453 (17) | 0.0436 (16) | 0.0533 (18) | 0.0007 (13) | 0.0122 (14) | 0.0118 (14) |
C32 | 0.0394 (16) | 0.0487 (17) | 0.0481 (17) | 0.0045 (13) | 0.0101 (13) | 0.0120 (13) |
O33 | 0.0589 (15) | 0.126 (2) | 0.0482 (14) | 0.0219 (15) | 0.0081 (11) | −0.0015 (14) |
C34 | 0.049 (2) | 0.156 (4) | 0.044 (2) | 0.004 (2) | 0.0133 (16) | 0.020 (2) |
C35 | 0.0477 (19) | 0.101 (3) | 0.0369 (17) | 0.000 (2) | 0.0135 (14) | 0.0116 (18) |
C36 | 0.059 (2) | 0.076 (2) | 0.057 (2) | −0.0181 (19) | 0.0090 (17) | 0.0108 (18) |
C37 | 0.058 (2) | 0.064 (2) | 0.059 (2) | −0.0014 (17) | 0.0086 (17) | 0.0100 (17) |
C38 | 0.0479 (18) | 0.065 (2) | 0.0356 (16) | −0.0002 (15) | 0.0067 (13) | 0.0060 (14) |
C39 | 0.060 (2) | 0.065 (2) | 0.056 (2) | 0.0037 (17) | 0.0121 (17) | −0.0003 (17) |
C40 | 0.062 (2) | 0.084 (3) | 0.063 (2) | 0.021 (2) | 0.0202 (18) | 0.0075 (19) |
C41 | 0.0518 (19) | 0.074 (2) | 0.0437 (18) | −0.0005 (17) | 0.0014 (15) | 0.0033 (16) |
O42 | 0.0573 (14) | 0.0734 (15) | 0.0452 (13) | 0.0201 (11) | 0.0039 (10) | 0.0149 (11) |
Geometric parameters (Å, º) top
S1—C8 | 1.797 (3) | C19—C20 | 1.369 (4) |
S1—C7 | 1.810 (3) | C19—H19 | 0.93 |
S2—C16 | 1.806 (3) | C20—C21 | 1.380 (4) |
S2—C15 | 1.811 (3) | C20—H20 | 0.93 |
S3—C23 | 1.801 (3) | C21—N22 | 1.337 (3) |
S3—C24 | 1.811 (3) | C21—C23 | 1.499 (4) |
S4—C31 | 1.798 (3) | C23—H23A | 0.97 |
S4—C32 | 1.810 (3) | C23—H23B | 0.97 |
N1—C2 | 1.332 (3) | C24—C25 | 1.498 (4) |
N1—C6 | 1.349 (3) | C24—H24A | 0.97 |
C2—C3 | 1.380 (4) | C24—H24B | 0.97 |
C2—C7 | 1.497 (4) | C25—C26 | 1.376 (4) |
C3—C4 | 1.368 (4) | C25—C30 | 1.392 (4) |
C3—H3 | 0.93 | C26—C27 | 1.380 (4) |
C4—C5 | 1.381 (4) | C26—H26 | 0.93 |
C4—H4 | 0.93 | C27—O42 | 1.376 (3) |
C5—C6 | 1.377 (4) | C27—C28 | 1.379 (4) |
C5—H5 | 0.93 | C28—C29 | 1.387 (4) |
C6—C32 | 1.489 (4) | C28—H28 | 0.93 |
C7—H7A | 0.97 | C29—C30 | 1.385 (4) |
C7—H7B | 0.97 | C29—C31 | 1.517 (4) |
C8—C9 | 1.515 (4) | C30—H30 | 0.93 |
C8—H8A | 0.97 | C31—H31A | 0.97 |
C8—H8B | 0.97 | C31—H31B | 0.97 |
C9—C14 | 1.379 (4) | C32—H32A | 0.97 |
C9—C10 | 1.385 (4) | C32—H32B | 0.97 |
C10—C11 | 1.380 (4) | O33—C34 | 1.430 (4) |
C10—H10 | 0.93 | C34—C35 | 1.507 (5) |
C11—C12 | 1.397 (4) | C34—H34A | 0.97 |
C11—C15 | 1.502 (4) | C34—H34B | 0.97 |
C12—C13 | 1.373 (4) | C35—C36 | 1.361 (5) |
C12—H12 | 0.93 | C35—C40 | 1.376 (5) |
C13—O33 | 1.373 (4) | C36—C37 | 1.384 (5) |
C13—C14 | 1.385 (4) | C36—H36 | 0.93 |
C14—H14 | 0.93 | C37—C38 | 1.382 (4) |
C15—H15A | 0.97 | C37—H37 | 0.93 |
C15—H15B | 0.97 | C38—C39 | 1.373 (5) |
C16—C17 | 1.493 (4) | C38—C41 | 1.502 (4) |
C16—H16A | 0.97 | C39—C40 | 1.372 (5) |
C16—H16B | 0.97 | C39—H39 | 0.93 |
C17—N22 | 1.340 (3) | C40—H40 | 0.93 |
C17—C18 | 1.374 (4) | C41—O42 | 1.423 (4) |
C18—C19 | 1.374 (4) | C41—H41A | 0.97 |
C18—H18 | 0.93 | C41—H41B | 0.97 |
| | | |
C8—S1—C7 | 101.54 (15) | C20—C21—C23 | 121.5 (3) |
C16—S2—C15 | 101.39 (15) | C17—N22—C21 | 117.9 (2) |
C23—S3—C24 | 101.37 (15) | C21—C23—S3 | 108.36 (19) |
C31—S4—C32 | 100.82 (14) | C21—C23—H23A | 110.0 |
C2—N1—C6 | 118.2 (2) | S3—C23—H23A | 110.0 |
N1—C2—C3 | 122.5 (3) | C21—C23—H23B | 110.0 |
N1—C2—C7 | 117.1 (3) | S3—C23—H23B | 110.0 |
C3—C2—C7 | 120.4 (3) | H23A—C23—H23B | 108.4 |
C4—C3—C2 | 119.3 (3) | C25—C24—S3 | 112.2 (2) |
C4—C3—H3 | 120.3 | C25—C24—H24A | 109.2 |
C2—C3—H3 | 120.3 | S3—C24—H24A | 109.2 |
C3—C4—C5 | 118.7 (3) | C25—C24—H24B | 109.2 |
C3—C4—H4 | 120.6 | S3—C24—H24B | 109.2 |
C5—C4—H4 | 120.6 | H24A—C24—H24B | 107.9 |
C6—C5—C4 | 119.2 (3) | C26—C25—C30 | 119.1 (3) |
C6—C5—H5 | 120.4 | C26—C25—C24 | 119.6 (3) |
C4—C5—H5 | 120.4 | C30—C25—C24 | 121.0 (3) |
N1—C6—C5 | 122.0 (3) | C25—C26—C27 | 120.8 (3) |
N1—C6—C32 | 115.7 (2) | C25—C26—H26 | 119.6 |
C5—C6—C32 | 122.3 (3) | C27—C26—H26 | 119.6 |
C2—C7—S1 | 113.89 (19) | O42—C27—C26 | 115.6 (3) |
C2—C7—H7A | 108.8 | O42—C27—C28 | 124.1 (3) |
S1—C7—H7A | 108.8 | C26—C27—C28 | 120.2 (3) |
C2—C7—H7B | 108.8 | C27—C28—C29 | 119.6 (3) |
S1—C7—H7B | 108.8 | C27—C28—H28 | 120.2 |
H7A—C7—H7B | 107.7 | C29—C28—H28 | 120.2 |
C9—C8—S1 | 116.2 (2) | C30—C29—C28 | 120.0 (3) |
C9—C8—H8A | 108.2 | C30—C29—C31 | 119.7 (3) |
S1—C8—H8A | 108.2 | C28—C29—C31 | 120.2 (3) |
C9—C8—H8B | 108.2 | C29—C30—C25 | 120.2 (3) |
S1—C8—H8B | 108.2 | C29—C30—H30 | 119.9 |
H8A—C8—H8B | 107.4 | C25—C30—H30 | 119.9 |
C14—C9—C10 | 119.3 (3) | C29—C31—S4 | 114.3 (2) |
C14—C9—C8 | 119.9 (3) | C29—C31—H31A | 108.7 |
C10—C9—C8 | 120.9 (3) | S4—C31—H31A | 108.7 |
C11—C10—C9 | 120.7 (3) | C29—C31—H31B | 108.7 |
C11—C10—H10 | 119.6 | S4—C31—H31B | 108.7 |
C9—C10—H10 | 119.6 | H31A—C31—H31B | 107.6 |
C10—C11—C12 | 119.4 (3) | C6—C32—S4 | 112.19 (19) |
C10—C11—C15 | 119.3 (3) | C6—C32—H32A | 109.2 |
C12—C11—C15 | 121.3 (2) | S4—C32—H32A | 109.2 |
C13—C12—C11 | 119.8 (3) | C6—C32—H32B | 109.2 |
C13—C12—H12 | 120.1 | S4—C32—H32B | 109.2 |
C11—C12—H12 | 120.1 | H32A—C32—H32B | 107.9 |
O33—C13—C12 | 125.3 (3) | C13—O33—C34 | 118.3 (3) |
O33—C13—C14 | 114.5 (3) | O33—C34—C35 | 112.8 (3) |
C12—C13—C14 | 120.2 (3) | O33—C34—H34A | 109.0 |
C9—C14—C13 | 120.4 (3) | C35—C34—H34A | 109.0 |
C9—C14—H14 | 119.8 | O33—C34—H34B | 109.0 |
C13—C14—H14 | 119.8 | C35—C34—H34B | 109.0 |
C11—C15—S2 | 113.3 (2) | H34A—C34—H34B | 107.8 |
C11—C15—H15A | 108.9 | C36—C35—C40 | 118.0 (3) |
S2—C15—H15A | 108.9 | C36—C35—C34 | 121.6 (4) |
C11—C15—H15B | 108.9 | C40—C35—C34 | 120.3 (4) |
S2—C15—H15B | 108.9 | C35—C36—C37 | 121.1 (3) |
H15A—C15—H15B | 107.7 | C35—C36—H36 | 119.4 |
C17—C16—S2 | 112.8 (2) | C37—C36—H36 | 119.4 |
C17—C16—H16A | 109.0 | C38—C37—C36 | 120.7 (3) |
S2—C16—H16A | 109.0 | C38—C37—H37 | 119.6 |
C17—C16—H16B | 109.0 | C36—C37—H37 | 119.6 |
S2—C16—H16B | 109.0 | C39—C38—C37 | 117.8 (3) |
H16A—C16—H16B | 107.8 | C39—C38—C41 | 121.2 (3) |
N22—C17—C18 | 122.7 (3) | C37—C38—C41 | 121.0 (3) |
N22—C17—C16 | 115.7 (2) | C40—C39—C38 | 121.0 (3) |
C18—C17—C16 | 121.6 (3) | C40—C39—H39 | 119.5 |
C19—C18—C17 | 119.1 (3) | C38—C39—H39 | 119.5 |
C19—C18—H18 | 120.4 | C39—C40—C35 | 121.4 (4) |
C17—C18—H18 | 120.4 | C39—C40—H40 | 119.3 |
C18—C19—C20 | 118.6 (3) | C35—C40—H40 | 119.3 |
C18—C19—H19 | 120.7 | O42—C41—C38 | 113.6 (2) |
C20—C19—H19 | 120.7 | O42—C41—H41A | 108.8 |
C19—C20—C21 | 119.5 (3) | C38—C41—H41A | 108.8 |
C19—C20—H20 | 120.2 | O42—C41—H41B | 108.8 |
C21—C20—H20 | 120.2 | C38—C41—H41B | 108.8 |
N22—C21—C20 | 122.1 (3) | H41A—C41—H41B | 107.7 |
N22—C21—C23 | 116.3 (2) | C27—O42—C41 | 116.4 (2) |
| | | |
C6—N1—C2—C3 | 2.9 (4) | N22—C21—C23—S3 | 92.1 (3) |
C6—N1—C2—C7 | −176.3 (2) | C20—C21—C23—S3 | −84.6 (3) |
N1—C2—C3—C4 | −2.1 (4) | C24—S3—C23—C21 | 164.6 (2) |
C7—C2—C3—C4 | 177.1 (3) | C23—S3—C24—C25 | 59.5 (3) |
C2—C3—C4—C5 | −0.7 (5) | S3—C24—C25—C26 | −96.9 (3) |
C3—C4—C5—C6 | 2.4 (5) | S3—C24—C25—C30 | 77.3 (3) |
C2—N1—C6—C5 | −1.1 (4) | C30—C25—C26—C27 | −2.0 (4) |
C2—N1—C6—C32 | −179.5 (2) | C24—C25—C26—C27 | 172.3 (3) |
C4—C5—C6—N1 | −1.6 (4) | C25—C26—C27—O42 | −175.7 (2) |
C4—C5—C6—C32 | 176.8 (3) | C25—C26—C27—C28 | 2.8 (4) |
N1—C2—C7—S1 | 118.2 (2) | O42—C27—C28—C29 | 176.6 (2) |
C3—C2—C7—S1 | −61.0 (3) | C26—C27—C28—C29 | −1.7 (4) |
C8—S1—C7—C2 | −78.2 (2) | C27—C28—C29—C30 | −0.1 (4) |
C7—S1—C8—C9 | 60.4 (3) | C27—C28—C29—C31 | −178.4 (3) |
S1—C8—C9—C14 | −130.9 (3) | C28—C29—C30—C25 | 0.8 (4) |
S1—C8—C9—C10 | 49.0 (3) | C31—C29—C30—C25 | 179.2 (2) |
C14—C9—C10—C11 | 1.2 (4) | C26—C25—C30—C29 | 0.2 (4) |
C8—C9—C10—C11 | −178.7 (3) | C24—C25—C30—C29 | −174.1 (3) |
C9—C10—C11—C12 | −1.8 (4) | C30—C29—C31—S4 | −131.4 (2) |
C9—C10—C11—C15 | 177.2 (3) | C28—C29—C31—S4 | 47.0 (3) |
C10—C11—C12—C13 | −0.1 (4) | C32—S4—C31—C29 | 60.1 (2) |
C15—C11—C12—C13 | −179.1 (3) | N1—C6—C32—S4 | 83.0 (3) |
C11—C12—C13—O33 | −178.7 (3) | C5—C6—C32—S4 | −95.5 (3) |
C11—C12—C13—C14 | 2.6 (4) | C31—S4—C32—C6 | 73.1 (2) |
C10—C9—C14—C13 | 1.3 (4) | C12—C13—O33—C34 | 18.8 (4) |
C8—C9—C14—C13 | −178.8 (3) | C14—C13—O33—C34 | −162.4 (3) |
O33—C13—C14—C9 | 177.9 (3) | C13—O33—C34—C35 | −96.5 (4) |
C12—C13—C14—C9 | −3.2 (4) | O33—C34—C35—C36 | 131.8 (4) |
C10—C11—C15—S2 | 84.9 (3) | O33—C34—C35—C40 | −51.3 (4) |
C12—C11—C15—S2 | −96.2 (3) | C40—C35—C36—C37 | −0.5 (5) |
C16—S2—C15—C11 | 80.4 (2) | C34—C35—C36—C37 | 176.5 (3) |
C15—S2—C16—C17 | 75.6 (2) | C35—C36—C37—C38 | 1.0 (5) |
S2—C16—C17—N22 | −79.9 (3) | C36—C37—C38—C39 | 0.0 (5) |
S2—C16—C17—C18 | 98.0 (3) | C36—C37—C38—C41 | 179.6 (3) |
N22—C17—C18—C19 | −0.3 (5) | C37—C38—C39—C40 | −1.5 (5) |
C16—C17—C18—C19 | −178.0 (3) | C41—C38—C39—C40 | 178.9 (3) |
C17—C18—C19—C20 | 0.9 (5) | C38—C39—C40—C35 | 2.1 (5) |
C18—C19—C20—C21 | 0.2 (4) | C36—C35—C40—C39 | −1.1 (5) |
C19—C20—C21—N22 | −1.9 (4) | C34—C35—C40—C39 | −178.1 (3) |
C19—C20—C21—C23 | 174.6 (3) | C39—C38—C41—O42 | 139.0 (3) |
C18—C17—N22—C21 | −1.4 (4) | C37—C38—C41—O42 | −40.6 (4) |
C16—C17—N22—C21 | 176.5 (2) | C26—C27—O42—C41 | 150.3 (3) |
C20—C21—N22—C17 | 2.5 (4) | C28—C27—O42—C41 | −28.1 (4) |
C23—C21—N22—C17 | −174.2 (2) | C38—C41—O42—C27 | −55.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15B···N22 | 0.97 | 2.46 | 3.220 (4) | 135 |
C23—H23B···O42i | 0.97 | 2.48 | 3.399 (3) | 158 |
C41—H41B···S4ii | 0.97 | 2.77 | 3.604 (3) | 145 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x, −y+1, −z. |
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