Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961700273X/yf3117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700273X/yf3117Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700273X/yf3117IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700273X/yf3117IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700273X/yf3117Isup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700273X/yf3117IIsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700273X/yf3117IIIsup7.cml |
CCDC references: 1533418; 1533417; 1533416
For all compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009) for (I), (III); SHELXL2014 (Sheldrick, 2015 and PLATON (Spek, 2009) for (II).
C21H19F4N3O2S | Dx = 1.510 Mg m−3 |
Mr = 453.45 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 4704 reflections |
a = 19.7282 (6) Å | θ = 2.1–27.8° |
b = 9.7644 (3) Å | µ = 0.22 mm−1 |
c = 20.7157 (7) Å | T = 296 K |
V = 3990.5 (2) Å3 | Block, colourless |
Z = 8 | 0.31 × 0.29 × 0.28 mm |
F(000) = 1872 |
Bruker Kappa APEXII diffractometer | 2738 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.039 |
φ and ω scans | θmax = 26.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 20012) | h = −22→24 |
Tmin = 0.926, Tmax = 0.939 | k = −12→12 |
50117 measured reflections | l = −25→26 |
4148 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.1039P)2 + 2.7804P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.210 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.35 e Å−3 |
4148 reflections | Δρmin = −0.53 e Å−3 |
282 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0032 (8) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.38650 (11) | 0.7471 (3) | 0.45255 (12) | 0.0452 (6) | |
N2 | 0.37282 (12) | 0.6640 (3) | 0.50338 (13) | 0.0464 (6) | |
C3 | 0.43251 (13) | 0.6512 (3) | 0.53422 (14) | 0.0412 (7) | |
C3A | 0.48364 (14) | 0.7256 (3) | 0.50227 (14) | 0.0402 (6) | |
C4 | 0.55757 (14) | 0.7426 (3) | 0.51515 (15) | 0.0435 (7) | |
H4A | 0.5649 | 0.7621 | 0.5605 | 0.052* | |
H4B | 0.5815 | 0.6588 | 0.5044 | 0.052* | |
N5 | 0.58350 (12) | 0.8571 (3) | 0.47532 (12) | 0.0450 (6) | |
C6 | 0.56076 (15) | 0.8565 (4) | 0.40750 (15) | 0.0498 (7) | |
H6A | 0.5721 | 0.7694 | 0.3877 | 0.060* | |
H6B | 0.5839 | 0.9283 | 0.3838 | 0.060* | |
C7 | 0.48439 (16) | 0.8792 (3) | 0.40391 (16) | 0.0492 (7) | |
H7A | 0.4736 | 0.9736 | 0.4143 | 0.059* | |
H7B | 0.4681 | 0.8599 | 0.3607 | 0.059* | |
C7A | 0.45184 (14) | 0.7861 (3) | 0.45089 (14) | 0.0430 (7) | |
C17 | 0.33306 (15) | 0.7798 (3) | 0.40629 (16) | 0.0512 (8) | |
H17A | 0.3421 | 0.8691 | 0.3876 | 0.061* | |
H17B | 0.2901 | 0.7850 | 0.4289 | 0.061* | |
C11 | 0.32736 (14) | 0.6760 (4) | 0.35284 (15) | 0.0482 (8) | |
C12 | 0.31506 (16) | 0.5384 (4) | 0.36714 (18) | 0.0562 (8) | |
H12 | 0.3117 | 0.5110 | 0.4100 | 0.067* | |
C13 | 0.30780 (18) | 0.4429 (4) | 0.3189 (2) | 0.0704 (11) | |
H13 | 0.3004 | 0.3512 | 0.3288 | 0.084* | |
C14 | 0.31172 (19) | 0.4851 (6) | 0.2564 (2) | 0.0766 (12) | |
F14 | 0.30351 (16) | 0.3926 (4) | 0.20841 (14) | 0.1188 (11) | |
C15 | 0.3238 (2) | 0.6185 (6) | 0.2395 (2) | 0.0806 (13) | |
H15 | 0.3265 | 0.6444 | 0.1964 | 0.097* | |
C16 | 0.33188 (17) | 0.7143 (4) | 0.28874 (18) | 0.0650 (10) | |
H16 | 0.3404 | 0.8053 | 0.2783 | 0.078* | |
C31 | 0.43545 (14) | 0.5722 (3) | 0.59446 (14) | 0.0413 (7) | |
C32 | 0.49679 (14) | 0.5259 (3) | 0.61880 (14) | 0.0452 (7) | |
H32 | 0.5364 | 0.5422 | 0.5957 | 0.054* | |
C33 | 0.50019 (16) | 0.4561 (3) | 0.67656 (15) | 0.0484 (7) | |
H33 | 0.5419 | 0.4273 | 0.6926 | 0.058* | |
C34 | 0.44176 (16) | 0.4290 (3) | 0.71045 (15) | 0.0480 (7) | |
C35 | 0.37958 (16) | 0.4711 (3) | 0.68658 (16) | 0.0531 (8) | |
H35 | 0.3400 | 0.4507 | 0.7089 | 0.064* | |
C36 | 0.37683 (15) | 0.5435 (3) | 0.62941 (16) | 0.0506 (8) | |
H36 | 0.3351 | 0.5736 | 0.6140 | 0.061* | |
C37 | 0.4453 (2) | 0.3459 (4) | 0.76991 (18) | 0.0622 (9) | |
F31 | 0.44298 (18) | 0.2127 (2) | 0.75781 (13) | 0.1069 (10) | |
F32 | 0.39575 (15) | 0.3710 (3) | 0.81152 (12) | 0.1023 (9) | |
F33 | 0.50207 (14) | 0.3661 (3) | 0.80380 (11) | 0.0960 (8) | |
S51 | 0.66482 (4) | 0.88817 (9) | 0.48509 (4) | 0.0538 (3) | |
O51 | 0.67969 (14) | 1.0121 (3) | 0.45186 (16) | 0.0803 (8) | |
O52 | 0.67724 (13) | 0.8798 (3) | 0.55280 (13) | 0.0733 (8) | |
C51 | 0.70896 (16) | 0.7557 (4) | 0.44678 (18) | 0.0609 (9) | |
H51A | 0.7567 | 0.7676 | 0.4536 | 0.091* | |
H51B | 0.6994 | 0.7576 | 0.4013 | 0.091* | |
H51C | 0.6949 | 0.6694 | 0.4644 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0343 (12) | 0.0517 (14) | 0.0497 (14) | 0.0055 (10) | −0.0031 (10) | 0.0008 (12) |
N2 | 0.0351 (12) | 0.0520 (15) | 0.0521 (15) | 0.0015 (11) | −0.0016 (10) | 0.0044 (12) |
C3 | 0.0310 (13) | 0.0428 (15) | 0.0499 (17) | 0.0013 (11) | 0.0000 (11) | −0.0025 (13) |
C3A | 0.0331 (14) | 0.0419 (16) | 0.0458 (15) | 0.0040 (11) | 0.0001 (11) | −0.0036 (12) |
C4 | 0.0348 (14) | 0.0476 (16) | 0.0481 (17) | −0.0029 (12) | −0.0013 (11) | 0.0006 (13) |
N5 | 0.0363 (13) | 0.0474 (14) | 0.0513 (15) | −0.0052 (11) | −0.0002 (10) | −0.0043 (11) |
C6 | 0.0439 (16) | 0.0561 (18) | 0.0495 (18) | −0.0020 (14) | 0.0024 (13) | 0.0025 (14) |
C7 | 0.0453 (17) | 0.0516 (18) | 0.0508 (18) | 0.0004 (13) | 0.0006 (13) | 0.0051 (14) |
C7A | 0.0358 (14) | 0.0469 (16) | 0.0462 (16) | 0.0041 (12) | −0.0003 (12) | −0.0023 (13) |
C17 | 0.0357 (15) | 0.0591 (19) | 0.059 (2) | 0.0086 (13) | −0.0078 (13) | 0.0046 (15) |
C11 | 0.0294 (14) | 0.067 (2) | 0.0482 (18) | 0.0074 (13) | −0.0031 (12) | 0.0018 (15) |
C12 | 0.0427 (17) | 0.068 (2) | 0.058 (2) | −0.0061 (15) | 0.0052 (14) | −0.0056 (17) |
C13 | 0.052 (2) | 0.081 (3) | 0.078 (3) | −0.0109 (19) | 0.0098 (18) | −0.015 (2) |
C14 | 0.049 (2) | 0.112 (4) | 0.068 (3) | −0.003 (2) | 0.0007 (17) | −0.029 (3) |
F14 | 0.103 (2) | 0.166 (3) | 0.088 (2) | −0.0128 (19) | −0.0001 (15) | −0.062 (2) |
C15 | 0.065 (3) | 0.129 (4) | 0.047 (2) | 0.016 (3) | −0.0060 (17) | −0.005 (2) |
C16 | 0.053 (2) | 0.079 (3) | 0.062 (2) | 0.0121 (17) | −0.0017 (16) | 0.014 (2) |
C31 | 0.0370 (14) | 0.0416 (15) | 0.0455 (16) | −0.0011 (12) | −0.0004 (11) | −0.0043 (13) |
C32 | 0.0358 (14) | 0.0487 (16) | 0.0511 (17) | −0.0020 (12) | 0.0021 (12) | 0.0038 (14) |
C33 | 0.0461 (16) | 0.0489 (17) | 0.0503 (17) | 0.0006 (13) | −0.0069 (13) | −0.0001 (14) |
C34 | 0.0543 (18) | 0.0451 (16) | 0.0445 (17) | −0.0033 (13) | 0.0017 (13) | −0.0016 (13) |
C35 | 0.0470 (17) | 0.0554 (19) | 0.057 (2) | −0.0004 (14) | 0.0135 (14) | 0.0025 (16) |
C36 | 0.0364 (15) | 0.0564 (19) | 0.059 (2) | 0.0045 (13) | 0.0035 (13) | 0.0036 (16) |
C37 | 0.077 (2) | 0.059 (2) | 0.050 (2) | −0.0042 (18) | 0.0008 (17) | 0.0042 (17) |
F31 | 0.181 (3) | 0.0580 (14) | 0.0817 (17) | −0.0065 (16) | −0.0127 (17) | 0.0183 (13) |
F32 | 0.108 (2) | 0.137 (2) | 0.0623 (15) | 0.0034 (17) | 0.0266 (14) | 0.0241 (15) |
F33 | 0.0966 (19) | 0.130 (2) | 0.0617 (14) | −0.0050 (16) | −0.0185 (13) | 0.0194 (14) |
S51 | 0.0414 (5) | 0.0556 (5) | 0.0644 (6) | −0.0143 (3) | 0.0013 (3) | −0.0099 (4) |
O51 | 0.0717 (17) | 0.0566 (15) | 0.113 (2) | −0.0264 (13) | 0.0075 (15) | 0.0034 (15) |
O52 | 0.0542 (15) | 0.107 (2) | 0.0590 (15) | −0.0233 (13) | −0.0064 (11) | −0.0212 (14) |
C51 | 0.0395 (16) | 0.075 (2) | 0.068 (2) | −0.0023 (16) | 0.0020 (15) | −0.0066 (18) |
N1—C7A | 1.344 (4) | C13—H13 | 0.9300 |
N1—N2 | 1.356 (4) | C14—F14 | 1.353 (5) |
N1—C17 | 1.460 (4) | C14—C15 | 1.369 (7) |
N2—C3 | 1.345 (4) | C15—C16 | 1.392 (6) |
C3—C3A | 1.408 (4) | C15—H15 | 0.9300 |
C3—C31 | 1.468 (4) | C16—H16 | 0.9300 |
C3A—C7A | 1.369 (4) | C31—C32 | 1.387 (4) |
C3A—C4 | 1.492 (4) | C31—C36 | 1.393 (4) |
C4—N5 | 1.480 (4) | C32—C33 | 1.379 (4) |
C4—H4A | 0.9700 | C32—H32 | 0.9300 |
C4—H4B | 0.9700 | C33—C34 | 1.375 (4) |
N5—C6 | 1.475 (4) | C33—H33 | 0.9300 |
N5—S51 | 1.645 (2) | C34—C35 | 1.385 (4) |
C6—C7 | 1.525 (4) | C34—C37 | 1.477 (5) |
C6—H6A | 0.9700 | C35—C36 | 1.380 (5) |
C6—H6B | 0.9700 | C35—H35 | 0.9300 |
C7—C7A | 1.479 (4) | C36—H36 | 0.9300 |
C7—H7A | 0.9700 | C37—F31 | 1.325 (4) |
C7—H7B | 0.9700 | C37—F32 | 1.326 (5) |
C17—C11 | 1.505 (5) | C37—F33 | 1.337 (4) |
C17—H17A | 0.9700 | S51—O51 | 1.423 (3) |
C17—H17B | 0.9700 | S51—O52 | 1.426 (3) |
C11—C16 | 1.383 (5) | S51—C51 | 1.749 (4) |
C11—C12 | 1.397 (5) | C51—H51A | 0.9600 |
C12—C13 | 1.374 (5) | C51—H51B | 0.9600 |
C12—H12 | 0.9300 | C51—H51C | 0.9600 |
C13—C14 | 1.361 (6) | ||
C7A—N1—N2 | 112.3 (2) | C14—C13—H13 | 120.7 |
C7A—N1—C17 | 127.8 (3) | C12—C13—H13 | 120.7 |
N2—N1—C17 | 119.8 (2) | F14—C14—C13 | 119.4 (5) |
C3—N2—N1 | 104.5 (2) | F14—C14—C15 | 117.9 (4) |
N2—C3—C3A | 110.9 (3) | C13—C14—C15 | 122.7 (4) |
N2—C3—C31 | 119.1 (2) | C14—C15—C16 | 118.2 (4) |
C3A—C3—C31 | 130.0 (3) | C14—C15—H15 | 120.9 |
C7A—C3A—C3 | 105.0 (2) | C16—C15—H15 | 120.9 |
C7A—C3A—C4 | 122.6 (3) | C11—C16—C15 | 120.9 (4) |
C3—C3A—C4 | 132.4 (3) | C11—C16—H16 | 119.5 |
N5—C4—C3A | 108.8 (2) | C15—C16—H16 | 119.5 |
N5—C4—H4A | 109.9 | C32—C31—C36 | 118.0 (3) |
C3A—C4—H4A | 109.9 | C32—C31—C3 | 121.0 (3) |
N5—C4—H4B | 109.9 | C36—C31—C3 | 121.0 (3) |
C3A—C4—H4B | 109.9 | C33—C32—C31 | 121.3 (3) |
H4A—C4—H4B | 108.3 | C33—C32—H32 | 119.4 |
C6—N5—C4 | 115.0 (2) | C31—C32—H32 | 119.4 |
C6—N5—S51 | 114.5 (2) | C34—C33—C32 | 119.8 (3) |
C4—N5—S51 | 114.06 (19) | C34—C33—H33 | 120.1 |
N5—C6—C7 | 110.3 (3) | C32—C33—H33 | 120.1 |
N5—C6—H6A | 109.6 | C33—C34—C35 | 120.2 (3) |
C7—C6—H6A | 109.6 | C33—C34—C37 | 119.5 (3) |
N5—C6—H6B | 109.6 | C35—C34—C37 | 120.2 (3) |
C7—C6—H6B | 109.6 | C36—C35—C34 | 119.5 (3) |
H6A—C6—H6B | 108.1 | C36—C35—H35 | 120.2 |
C7A—C7—C6 | 107.9 (3) | C34—C35—H35 | 120.2 |
C7A—C7—H7A | 110.1 | C35—C36—C31 | 121.1 (3) |
C6—C7—H7A | 110.1 | C35—C36—H36 | 119.5 |
C7A—C7—H7B | 110.1 | C31—C36—H36 | 119.5 |
C6—C7—H7B | 110.1 | F31—C37—F32 | 106.2 (3) |
H7A—C7—H7B | 108.4 | F31—C37—F33 | 105.9 (3) |
N1—C7A—C3A | 107.3 (3) | F32—C37—F33 | 104.4 (3) |
N1—C7A—C7 | 127.4 (3) | F31—C37—C34 | 112.4 (3) |
C3A—C7A—C7 | 125.3 (3) | F32—C37—C34 | 113.9 (3) |
N1—C17—C11 | 112.9 (2) | F33—C37—C34 | 113.3 (3) |
N1—C17—H17A | 109.0 | O51—S51—O52 | 119.30 (18) |
C11—C17—H17A | 109.0 | O51—S51—N5 | 107.37 (16) |
N1—C17—H17B | 109.0 | O52—S51—N5 | 106.14 (14) |
C11—C17—H17B | 109.0 | O51—S51—C51 | 107.85 (19) |
H17A—C17—H17B | 107.8 | O52—S51—C51 | 108.55 (18) |
C16—C11—C12 | 118.4 (3) | N5—S51—C51 | 107.04 (15) |
C16—C11—C17 | 121.3 (3) | S51—C51—H51A | 109.5 |
C12—C11—C17 | 120.3 (3) | S51—C51—H51B | 109.5 |
C13—C12—C11 | 121.1 (4) | H51A—C51—H51B | 109.5 |
C13—C12—H12 | 119.4 | S51—C51—H51C | 109.5 |
C11—C12—H12 | 119.4 | H51A—C51—H51C | 109.5 |
C14—C13—C12 | 118.7 (4) | H51B—C51—H51C | 109.5 |
C7A—N1—N2—C3 | −0.1 (3) | C12—C13—C14—C15 | 1.2 (6) |
C17—N1—N2—C3 | 177.8 (3) | F14—C14—C15—C16 | 179.6 (3) |
N1—N2—C3—C3A | −0.5 (3) | C13—C14—C15—C16 | −0.4 (6) |
N1—N2—C3—C31 | 176.9 (3) | C12—C11—C16—C15 | 0.5 (5) |
N2—C3—C3A—C7A | 0.9 (3) | C17—C11—C16—C15 | −177.4 (3) |
C31—C3—C3A—C7A | −176.2 (3) | C14—C15—C16—C11 | −0.4 (6) |
N2—C3—C3A—C4 | −178.3 (3) | N2—C3—C31—C32 | 162.9 (3) |
C31—C3—C3A—C4 | 4.6 (5) | C3A—C3—C31—C32 | −20.2 (5) |
C7A—C3A—C4—N5 | 13.9 (4) | N2—C3—C31—C36 | −18.1 (4) |
C3—C3A—C4—N5 | −167.0 (3) | C3A—C3—C31—C36 | 158.7 (3) |
C3A—C4—N5—C6 | −45.2 (3) | C36—C31—C32—C33 | −1.4 (5) |
C3A—C4—N5—S51 | 179.6 (2) | C3—C31—C32—C33 | 177.5 (3) |
C4—N5—C6—C7 | 65.6 (3) | C31—C32—C33—C34 | 1.3 (5) |
S51—N5—C6—C7 | −159.4 (2) | C32—C33—C34—C35 | 0.3 (5) |
N5—C6—C7—C7A | −47.9 (3) | C32—C33—C34—C37 | 175.7 (3) |
N2—N1—C7A—C3A | 0.7 (3) | C33—C34—C35—C36 | −1.7 (5) |
C17—N1—C7A—C3A | −177.0 (3) | C37—C34—C35—C36 | −177.1 (3) |
N2—N1—C7A—C7 | −178.0 (3) | C34—C35—C36—C31 | 1.5 (5) |
C17—N1—C7A—C7 | 4.3 (5) | C32—C31—C36—C35 | 0.0 (5) |
C3—C3A—C7A—N1 | −0.9 (3) | C3—C31—C36—C35 | −178.9 (3) |
C4—C3A—C7A—N1 | 178.4 (3) | C33—C34—C37—F31 | −85.3 (4) |
C3—C3A—C7A—C7 | 177.8 (3) | C35—C34—C37—F31 | 90.1 (4) |
C4—C3A—C7A—C7 | −2.9 (5) | C33—C34—C37—F32 | 153.9 (3) |
C6—C7—C7A—N1 | −161.8 (3) | C35—C34—C37—F32 | −30.7 (5) |
C6—C7—C7A—C3A | 19.7 (4) | C33—C34—C37—F33 | 34.7 (5) |
C7A—N1—C17—C11 | 90.4 (4) | C35—C34—C37—F33 | −149.9 (3) |
N2—N1—C17—C11 | −87.2 (3) | C6—N5—S51—O51 | 53.3 (3) |
N1—C17—C11—C16 | −124.1 (3) | C4—N5—S51—O51 | −171.2 (2) |
N1—C17—C11—C12 | 58.1 (4) | C6—N5—S51—O52 | −178.0 (2) |
C16—C11—C12—C13 | 0.2 (5) | C4—N5—S51—O52 | −42.6 (3) |
C17—C11—C12—C13 | 178.1 (3) | C6—N5—S51—C51 | −62.2 (3) |
C11—C12—C13—C14 | −1.1 (5) | C4—N5—S51—C51 | 73.2 (2) |
C12—C13—C14—F14 | −178.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···Cg2i | 0.97 | 2.76 | 3.694 (4) | 161 |
C33—H33···Cg1i | 0.93 | 2.73 | 3.595 (3) | 154 |
C51—H51A···N2ii | 0.96 | 2.55 | 3.483 (4) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
C21H19ClF3N3O2S | Dx = 1.464 Mg m−3 |
Mr = 469.90 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 5856 reflections |
a = 5.4468 (2) Å | θ = 1.2–29.3° |
b = 11.4102 (4) Å | µ = 0.33 mm−1 |
c = 34.3009 (9) Å | T = 296 K |
V = 2131.77 (12) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
F(000) = 968 |
Bruker Kappa APEXII diffractometer | 3587 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.032 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −3→7 |
Tmin = 0.879, Tmax = 0.907 | k = −14→14 |
15002 measured reflections | l = −44→29 |
4920 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0426P)2 + 0.0545P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.16 e Å−3 |
4920 reflections | Δρmin = −0.22 e Å−3 |
309 parameters | Absolute structure: Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.03 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.6422 (4) | 0.5128 (2) | 0.64083 (7) | 0.0435 (6) | |
N2 | 0.7153 (4) | 0.5746 (2) | 0.60944 (7) | 0.0430 (6) | |
C3 | 0.5874 (5) | 0.6739 (3) | 0.61079 (7) | 0.0363 (6) | |
C3A | 0.4302 (5) | 0.6749 (3) | 0.64357 (7) | 0.0355 (6) | |
C4 | 0.2561 (5) | 0.7637 (3) | 0.65979 (8) | 0.0393 (7) | |
H4A | 0.3280 | 0.8414 | 0.6585 | 0.047* | |
H4B | 0.1045 | 0.7639 | 0.6450 | 0.047* | |
N5 | 0.2071 (4) | 0.7314 (2) | 0.70082 (7) | 0.0401 (6) | |
C6 | 0.1312 (6) | 0.6083 (3) | 0.70578 (9) | 0.0506 (8) | |
H6A | −0.0004 | 0.5900 | 0.6877 | 0.061* | |
H6B | 0.0712 | 0.5961 | 0.7321 | 0.061* | |
C7 | 0.3479 (6) | 0.5294 (3) | 0.69817 (9) | 0.0502 (8) | |
H7A | 0.4623 | 0.5333 | 0.7198 | 0.060* | |
H7B | 0.2934 | 0.4489 | 0.6953 | 0.060* | |
C7A | 0.4698 (5) | 0.5696 (3) | 0.66161 (8) | 0.0395 (7) | |
C17 | 0.7330 (6) | 0.3936 (3) | 0.64656 (10) | 0.0556 (9) | |
H17A | 0.7849 | 0.3841 | 0.6734 | 0.067* | |
H17B | 0.8748 | 0.3808 | 0.6300 | 0.067* | |
C11 | 0.5399 (6) | 0.3036 (3) | 0.63724 (9) | 0.0497 (8) | |
C12 | 0.4368 (8) | 0.2988 (3) | 0.60081 (10) | 0.0666 (10) | |
H12 | 0.4922 | 0.3496 | 0.5815 | 0.080* | |
C13 | 0.2532 (9) | 0.2204 (3) | 0.59234 (11) | 0.0733 (12) | |
H13 | 0.1822 | 0.2191 | 0.5677 | 0.088* | |
C14 | 0.1756 (7) | 0.1438 (3) | 0.62071 (11) | 0.0611 (10) | |
Cl14 | −0.0571 (2) | 0.04450 (10) | 0.61044 (4) | 0.0892 (4) | |
C15 | 0.2776 (8) | 0.1455 (3) | 0.65713 (11) | 0.0694 (11) | |
H15 | 0.2257 | 0.0930 | 0.6762 | 0.083* | |
C16 | 0.4585 (8) | 0.2263 (3) | 0.66515 (10) | 0.0646 (10) | |
H16 | 0.5270 | 0.2286 | 0.6900 | 0.078* | |
C31 | 0.6213 (5) | 0.7627 (3) | 0.58017 (8) | 0.0377 (7) | |
C32 | 0.4564 (6) | 0.8528 (3) | 0.57475 (9) | 0.0494 (8) | |
H32 | 0.3189 | 0.8575 | 0.5908 | 0.059* | |
C33 | 0.4902 (6) | 0.9359 (3) | 0.54621 (9) | 0.0549 (9) | |
H33 | 0.3775 | 0.9964 | 0.5432 | 0.066* | |
C34 | 0.6925 (7) | 0.9287 (3) | 0.52216 (9) | 0.0529 (9) | |
C35 | 0.8556 (6) | 0.8382 (3) | 0.52649 (9) | 0.0575 (9) | |
H35 | 0.9899 | 0.8323 | 0.5099 | 0.069* | |
C36 | 0.8215 (6) | 0.7563 (3) | 0.55522 (9) | 0.0485 (8) | |
H36 | 0.9341 | 0.6957 | 0.5580 | 0.058* | |
C37 | 0.7371 (10) | 1.0200 (5) | 0.49169 (13) | 0.0752 (12) | |
F31A | 0.875 (5) | 1.0995 (15) | 0.5014 (5) | 0.134 (7) | 0.51 (2) |
F32A | 0.812 (4) | 0.9771 (12) | 0.4588 (4) | 0.143 (9) | 0.51 (2) |
F33A | 0.537 (3) | 1.073 (2) | 0.4812 (5) | 0.129 (6) | 0.51 (2) |
F31B | 0.974 (3) | 1.050 (2) | 0.4901 (7) | 0.147 (9) | 0.49 (2) |
F32B | 0.680 (6) | 0.995 (2) | 0.4590 (4) | 0.183 (10) | 0.49 (2) |
F33B | 0.635 (7) | 1.1226 (14) | 0.5013 (9) | 0.188 (11) | 0.49 (2) |
S51 | 0.07584 (13) | 0.83056 (8) | 0.72794 (2) | 0.0464 (2) | |
O51 | 0.0454 (5) | 0.7815 (3) | 0.76567 (6) | 0.0724 (8) | |
O52 | 0.2154 (4) | 0.9352 (2) | 0.72410 (7) | 0.0565 (6) | |
C51 | −0.2150 (6) | 0.8583 (4) | 0.70770 (11) | 0.0795 (14) | |
H51A | −0.2939 | 0.9200 | 0.7220 | 0.119* | |
H51B | −0.3132 | 0.7885 | 0.7091 | 0.119* | |
H51C | −0.1967 | 0.8815 | 0.6810 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0500 (15) | 0.0338 (15) | 0.0467 (14) | 0.0050 (12) | 0.0004 (12) | 0.0033 (11) |
N2 | 0.0479 (14) | 0.0397 (15) | 0.0415 (13) | 0.0025 (12) | 0.0018 (11) | 0.0005 (11) |
C3 | 0.0369 (13) | 0.0354 (16) | 0.0367 (14) | 0.0011 (14) | −0.0013 (12) | −0.0024 (12) |
C3A | 0.0378 (13) | 0.0335 (16) | 0.0351 (13) | −0.0019 (14) | 0.0004 (12) | −0.0016 (12) |
C4 | 0.0377 (14) | 0.0417 (18) | 0.0386 (15) | 0.0010 (14) | 0.0025 (12) | 0.0002 (13) |
N5 | 0.0378 (12) | 0.0459 (16) | 0.0367 (12) | −0.0060 (12) | 0.0070 (10) | −0.0030 (11) |
C6 | 0.053 (2) | 0.049 (2) | 0.0502 (18) | −0.0140 (16) | 0.0085 (15) | 0.0020 (15) |
C7 | 0.059 (2) | 0.044 (2) | 0.0474 (18) | −0.0066 (16) | 0.0040 (15) | 0.0090 (15) |
C7A | 0.0430 (16) | 0.0348 (17) | 0.0406 (15) | −0.0022 (13) | −0.0013 (13) | 0.0005 (13) |
C17 | 0.061 (2) | 0.039 (2) | 0.066 (2) | 0.0127 (17) | −0.0060 (18) | 0.0059 (16) |
C11 | 0.069 (2) | 0.0321 (17) | 0.0482 (17) | 0.0109 (16) | −0.0067 (16) | −0.0002 (14) |
C12 | 0.103 (3) | 0.046 (2) | 0.0510 (19) | 0.001 (2) | −0.014 (2) | 0.0062 (16) |
C13 | 0.113 (3) | 0.048 (2) | 0.059 (2) | 0.005 (2) | −0.033 (2) | −0.0026 (18) |
C14 | 0.073 (2) | 0.037 (2) | 0.073 (2) | 0.0063 (18) | −0.0073 (19) | −0.0168 (18) |
Cl14 | 0.0822 (7) | 0.0607 (7) | 0.1248 (9) | −0.0037 (6) | −0.0140 (7) | −0.0279 (7) |
C15 | 0.099 (3) | 0.047 (2) | 0.062 (2) | −0.013 (2) | 0.004 (2) | 0.0018 (18) |
C16 | 0.098 (3) | 0.049 (2) | 0.0466 (18) | −0.006 (2) | −0.0124 (19) | 0.0037 (16) |
C31 | 0.0379 (15) | 0.0381 (17) | 0.0370 (14) | −0.0030 (13) | 0.0011 (12) | −0.0026 (13) |
C32 | 0.0515 (18) | 0.050 (2) | 0.0467 (17) | 0.0068 (17) | 0.0100 (14) | 0.0082 (15) |
C33 | 0.063 (2) | 0.046 (2) | 0.055 (2) | 0.0091 (17) | 0.0020 (16) | 0.0097 (16) |
C34 | 0.069 (2) | 0.051 (2) | 0.0389 (17) | −0.0099 (19) | 0.0052 (16) | 0.0052 (15) |
C35 | 0.061 (2) | 0.059 (2) | 0.0528 (19) | −0.0081 (19) | 0.0214 (15) | 0.0021 (17) |
C36 | 0.0509 (17) | 0.046 (2) | 0.0482 (17) | 0.0046 (16) | 0.0109 (14) | −0.0010 (15) |
C37 | 0.096 (3) | 0.066 (3) | 0.064 (3) | −0.016 (3) | 0.009 (3) | 0.017 (2) |
F31A | 0.19 (2) | 0.084 (9) | 0.130 (9) | −0.075 (11) | −0.025 (11) | 0.029 (7) |
F32A | 0.260 (19) | 0.093 (7) | 0.077 (8) | 0.022 (10) | 0.103 (12) | 0.025 (6) |
F33A | 0.144 (8) | 0.141 (13) | 0.101 (8) | 0.046 (8) | 0.029 (6) | 0.081 (8) |
F31B | 0.102 (8) | 0.172 (18) | 0.165 (16) | −0.057 (8) | −0.009 (6) | 0.120 (14) |
F32B | 0.290 (19) | 0.193 (19) | 0.065 (9) | −0.167 (16) | −0.075 (11) | 0.069 (9) |
F33B | 0.32 (3) | 0.081 (8) | 0.166 (15) | 0.041 (12) | 0.110 (19) | 0.069 (8) |
S51 | 0.0359 (4) | 0.0627 (5) | 0.0406 (4) | −0.0030 (4) | 0.0025 (3) | −0.0132 (4) |
O51 | 0.0878 (16) | 0.092 (2) | 0.0379 (12) | −0.0073 (16) | 0.0147 (12) | −0.0082 (12) |
O52 | 0.0480 (12) | 0.0539 (16) | 0.0676 (14) | −0.0022 (11) | 0.0040 (11) | −0.0185 (12) |
C51 | 0.0346 (17) | 0.123 (4) | 0.080 (3) | 0.011 (2) | −0.0040 (17) | −0.034 (3) |
N1—C7A | 1.346 (4) | C14—C15 | 1.367 (5) |
N1—N2 | 1.347 (3) | C14—Cl14 | 1.736 (4) |
N1—C17 | 1.461 (4) | C15—C16 | 1.377 (5) |
N2—C3 | 1.332 (4) | C15—H15 | 0.9300 |
C3—C3A | 1.413 (4) | C16—H16 | 0.9300 |
C3—C31 | 1.471 (4) | C31—C32 | 1.378 (4) |
C3A—C7A | 1.368 (4) | C31—C36 | 1.388 (4) |
C3A—C4 | 1.496 (4) | C32—C33 | 1.375 (4) |
C4—N5 | 1.479 (4) | C32—H32 | 0.9300 |
C4—H4A | 0.9700 | C33—C34 | 1.379 (5) |
C4—H4B | 0.9700 | C33—H33 | 0.9300 |
N5—C6 | 1.473 (4) | C34—C35 | 1.370 (5) |
N5—S51 | 1.630 (3) | C34—C37 | 1.495 (5) |
C6—C7 | 1.507 (4) | C35—C36 | 1.371 (5) |
C6—H6A | 0.9700 | C35—H35 | 0.9300 |
C6—H6B | 0.9700 | C36—H36 | 0.9300 |
C7—C7A | 1.491 (4) | C37—F32B | 1.199 (12) |
C7—H7A | 0.9700 | C37—F31A | 1.224 (15) |
C7—H7B | 0.9700 | C37—F32A | 1.297 (10) |
C17—C11 | 1.504 (5) | C37—F33A | 1.302 (13) |
C17—H17A | 0.9700 | C37—F31B | 1.336 (15) |
C17—H17B | 0.9700 | C37—F33B | 1.338 (16) |
C11—C12 | 1.371 (5) | S51—O51 | 1.420 (2) |
C11—C16 | 1.375 (5) | S51—O52 | 1.421 (2) |
C12—C13 | 1.373 (6) | S51—C51 | 1.758 (3) |
C12—H12 | 0.9300 | C51—H51A | 0.9600 |
C13—C14 | 1.374 (5) | C51—H51B | 0.9600 |
C13—H13 | 0.9300 | C51—H51C | 0.9600 |
C7A—N1—N2 | 112.2 (2) | C15—C14—Cl14 | 119.4 (3) |
C7A—N1—C17 | 127.9 (3) | C13—C14—Cl14 | 119.7 (3) |
N2—N1—C17 | 119.7 (3) | C14—C15—C16 | 118.8 (4) |
C3—N2—N1 | 105.3 (2) | C14—C15—H15 | 120.6 |
N2—C3—C3A | 110.5 (3) | C16—C15—H15 | 120.6 |
N2—C3—C31 | 119.7 (2) | C11—C16—C15 | 121.4 (3) |
C3A—C3—C31 | 129.7 (3) | C11—C16—H16 | 119.3 |
C7A—C3A—C3 | 104.9 (2) | C15—C16—H16 | 119.3 |
C7A—C3A—C4 | 121.8 (2) | C32—C31—C36 | 117.9 (3) |
C3—C3A—C4 | 133.3 (3) | C32—C31—C3 | 121.9 (2) |
N5—C4—C3A | 107.4 (2) | C36—C31—C3 | 120.2 (3) |
N5—C4—H4A | 110.2 | C33—C32—C31 | 121.5 (3) |
C3A—C4—H4A | 110.2 | C33—C32—H32 | 119.2 |
N5—C4—H4B | 110.2 | C31—C32—H32 | 119.2 |
C3A—C4—H4B | 110.2 | C32—C33—C34 | 119.5 (3) |
H4A—C4—H4B | 108.5 | C32—C33—H33 | 120.3 |
C6—N5—C4 | 113.5 (2) | C34—C33—H33 | 120.3 |
C6—N5—S51 | 118.21 (19) | C35—C34—C33 | 119.9 (3) |
C4—N5—S51 | 116.6 (2) | C35—C34—C37 | 119.7 (3) |
N5—C6—C7 | 109.2 (2) | C33—C34—C37 | 120.4 (4) |
N5—C6—H6A | 109.8 | C34—C35—C36 | 120.2 (3) |
C7—C6—H6A | 109.8 | C34—C35—H35 | 119.9 |
N5—C6—H6B | 109.8 | C36—C35—H35 | 119.9 |
C7—C6—H6B | 109.8 | C35—C36—C31 | 120.9 (3) |
H6A—C6—H6B | 108.3 | C35—C36—H36 | 119.5 |
C7A—C7—C6 | 108.1 (3) | C31—C36—H36 | 119.5 |
C7A—C7—H7A | 110.1 | F31A—C37—F32A | 108.8 (10) |
C6—C7—H7A | 110.1 | F31A—C37—F33A | 104.0 (10) |
C7A—C7—H7B | 110.1 | F32A—C37—F33A | 101.6 (9) |
C6—C7—H7B | 110.1 | F32B—C37—F31B | 105.9 (11) |
H7A—C7—H7B | 108.4 | F32B—C37—F33B | 109.3 (13) |
N1—C7A—C3A | 107.1 (2) | F31B—C37—F33B | 100.7 (12) |
N1—C7A—C7 | 127.4 (3) | F32B—C37—C34 | 116.4 (8) |
C3A—C7A—C7 | 125.5 (3) | F31A—C37—C34 | 115.2 (8) |
N1—C17—C11 | 111.7 (3) | F32A—C37—C34 | 113.4 (7) |
N1—C17—H17A | 109.3 | F33A—C37—C34 | 112.6 (7) |
C11—C17—H17A | 109.3 | F31B—C37—C34 | 111.5 (7) |
N1—C17—H17B | 109.3 | F33B—C37—C34 | 111.7 (8) |
C11—C17—H17B | 109.3 | O51—S51—O52 | 118.56 (16) |
H17A—C17—H17B | 107.9 | O51—S51—N5 | 107.30 (15) |
C12—C11—C16 | 118.5 (3) | O52—S51—N5 | 107.20 (13) |
C12—C11—C17 | 120.5 (3) | O51—S51—C51 | 109.00 (19) |
C16—C11—C17 | 121.0 (3) | O52—S51—C51 | 107.11 (19) |
C11—C12—C13 | 121.1 (4) | N5—S51—C51 | 107.16 (16) |
C11—C12—H12 | 119.4 | S51—C51—H51A | 109.5 |
C13—C12—H12 | 119.4 | S51—C51—H51B | 109.5 |
C12—C13—C14 | 119.2 (3) | H51A—C51—H51B | 109.5 |
C12—C13—H13 | 120.4 | S51—C51—H51C | 109.5 |
C14—C13—H13 | 120.4 | H51A—C51—H51C | 109.5 |
C15—C14—C13 | 120.9 (4) | H51B—C51—H51C | 109.5 |
C7A—N1—N2—C3 | 0.8 (3) | C12—C11—C16—C15 | −0.1 (6) |
C17—N1—N2—C3 | 175.0 (3) | C17—C11—C16—C15 | 178.4 (3) |
N1—N2—C3—C3A | −0.1 (3) | C14—C15—C16—C11 | −0.9 (6) |
N1—N2—C3—C31 | −179.5 (2) | N2—C3—C31—C32 | 164.3 (3) |
N2—C3—C3A—C7A | −0.5 (3) | C3A—C3—C31—C32 | −15.0 (5) |
C31—C3—C3A—C7A | 178.8 (3) | N2—C3—C31—C36 | −14.6 (4) |
N2—C3—C3A—C4 | 177.5 (3) | C3A—C3—C31—C36 | 166.1 (3) |
C31—C3—C3A—C4 | −3.1 (5) | C36—C31—C32—C33 | −1.5 (5) |
C7A—C3A—C4—N5 | 16.3 (4) | C3—C31—C32—C33 | 179.6 (3) |
C3—C3A—C4—N5 | −161.6 (3) | C31—C32—C33—C34 | 0.6 (5) |
C3A—C4—N5—C6 | −51.5 (3) | C32—C33—C34—C35 | 1.0 (5) |
C3A—C4—N5—S51 | 165.85 (18) | C32—C33—C34—C37 | −178.2 (4) |
C4—N5—C6—C7 | 70.6 (3) | C33—C34—C35—C36 | −1.6 (5) |
S51—N5—C6—C7 | −147.5 (2) | C37—C34—C35—C36 | 177.7 (4) |
N5—C6—C7—C7A | −46.5 (3) | C34—C35—C36—C31 | 0.6 (5) |
N2—N1—C7A—C3A | −1.2 (3) | C32—C31—C36—C35 | 1.0 (5) |
C17—N1—C7A—C3A | −174.8 (3) | C3—C31—C36—C35 | 179.9 (3) |
N2—N1—C7A—C7 | −179.3 (3) | C35—C34—C37—F32B | 80 (2) |
C17—N1—C7A—C7 | 7.0 (5) | C33—C34—C37—F32B | −100 (2) |
C3—C3A—C7A—N1 | 1.0 (3) | C35—C34—C37—F31A | −84.2 (17) |
C4—C3A—C7A—N1 | −177.4 (2) | C33—C34—C37—F31A | 95.0 (17) |
C3—C3A—C7A—C7 | 179.2 (3) | C35—C34—C37—F32A | 42.1 (13) |
C4—C3A—C7A—C7 | 0.8 (4) | C33—C34—C37—F32A | −138.7 (13) |
C6—C7—C7A—N1 | −167.7 (3) | C35—C34—C37—F33A | 156.8 (14) |
C6—C7—C7A—C3A | 14.5 (4) | C33—C34—C37—F33A | −24.0 (15) |
C7A—N1—C17—C11 | 68.1 (4) | C35—C34—C37—F31B | −41.3 (17) |
N2—N1—C17—C11 | −105.1 (3) | C33—C34—C37—F31B | 137.9 (17) |
N1—C17—C11—C12 | 59.0 (4) | C35—C34—C37—F33B | −153 (2) |
N1—C17—C11—C16 | −119.4 (4) | C33—C34—C37—F33B | 26 (2) |
C16—C11—C12—C13 | 1.2 (5) | C6—N5—S51—O51 | 38.9 (3) |
C17—C11—C12—C13 | −177.3 (3) | C4—N5—S51—O51 | 179.7 (2) |
C11—C12—C13—C14 | −1.4 (6) | C6—N5—S51—O52 | 167.3 (2) |
C12—C13—C14—C15 | 0.4 (6) | C4—N5—S51—O52 | −51.9 (2) |
C12—C13—C14—Cl14 | 179.8 (3) | C6—N5—S51—C51 | −78.0 (3) |
C13—C14—C15—C16 | 0.7 (6) | C4—N5—S51—C51 | 62.8 (3) |
Cl14—C14—C15—C16 | −178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O52i | 0.93 | 2.44 | 3.339 (4) | 163 |
C17—H17A···O51ii | 0.97 | 2.57 | 3.487 (4) | 158 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+3/2. |
C22H22F3N3O2S | F(000) = 936 |
Mr = 449.48 | Dx = 1.427 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8408 (10) Å | Cell parameters from 4392 reflections |
b = 8.7145 (6) Å | θ = 1.7–26.7° |
c = 18.0898 (13) Å | µ = 0.21 mm−1 |
β = 106.470 (2)° | T = 296 K |
V = 2092.4 (3) Å3 | Block, colourless |
Z = 4 | 0.34 × 0.24 × 0.22 mm |
Bruker Kappa APEXII diffractometer | 2953 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.045 |
φ and ω scans | θmax = 26.7°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −17→17 |
Tmin = 0.946, Tmax = 0.956 | k = −10→10 |
33310 measured reflections | l = −22→22 |
4391 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0394P)2 + 1.101P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4391 reflections | Δρmax = 0.33 e Å−3 |
310 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.73177 (12) | 0.6156 (2) | 0.51672 (9) | 0.0328 (4) | |
N2 | 0.69346 (12) | 0.6065 (2) | 0.57743 (9) | 0.0331 (4) | |
C3 | 0.59874 (14) | 0.6585 (2) | 0.55104 (11) | 0.0292 (4) | |
C3A | 0.57717 (14) | 0.7005 (2) | 0.47255 (11) | 0.0301 (4) | |
C4 | 0.48518 (15) | 0.7636 (3) | 0.41515 (11) | 0.0364 (5) | |
H4A | 0.4267 | 0.7024 | 0.4153 | 0.044* | |
H4B | 0.4733 | 0.8682 | 0.4286 | 0.044* | |
N5 | 0.50150 (13) | 0.7597 (2) | 0.33856 (10) | 0.0383 (4) | |
C6 | 0.60024 (16) | 0.8150 (3) | 0.33435 (13) | 0.0443 (6) | |
H6A | 0.6132 | 0.9164 | 0.3571 | 0.053* | |
H6B | 0.6006 | 0.8220 | 0.2809 | 0.053* | |
C7 | 0.68157 (16) | 0.7042 (3) | 0.37754 (12) | 0.0406 (5) | |
H7A | 0.6783 | 0.6100 | 0.3484 | 0.049* | |
H7B | 0.7477 | 0.7495 | 0.3850 | 0.049* | |
C7A | 0.66397 (15) | 0.6718 (2) | 0.45297 (11) | 0.0321 (5) | |
C17 | 0.83560 (14) | 0.5690 (3) | 0.52546 (13) | 0.0375 (5) | |
H17A | 0.8755 | 0.5907 | 0.5778 | 0.045* | |
H17B | 0.8624 | 0.6301 | 0.4910 | 0.045* | |
C11 | 0.84674 (14) | 0.4017 (3) | 0.50869 (12) | 0.0369 (5) | |
C12 | 0.81108 (16) | 0.2891 (3) | 0.54804 (13) | 0.0419 (5) | |
H12 | 0.7796 | 0.3181 | 0.5850 | 0.050* | |
C13 | 0.82091 (18) | 0.1344 (3) | 0.53402 (15) | 0.0527 (7) | |
C14 | 0.8700 (2) | 0.0946 (4) | 0.47966 (18) | 0.0693 (9) | |
H14 | 0.8783 | −0.0086 | 0.4697 | 0.083* | |
C15 | 0.9063 (2) | 0.2042 (4) | 0.44039 (19) | 0.0704 (9) | |
H15 | 0.9393 | 0.1749 | 0.4044 | 0.084* | |
C16 | 0.89437 (17) | 0.3587 (3) | 0.45389 (14) | 0.0529 (7) | |
H16 | 0.9181 | 0.4330 | 0.4265 | 0.063* | |
C18 | 0.7774 (2) | 0.0146 (3) | 0.57530 (18) | 0.0787 (9) | |
H18A | 0.7133 | −0.0185 | 0.5427 | 0.118* | |
H18B | 0.7687 | 0.0573 | 0.6219 | 0.118* | |
H18C | 0.8223 | −0.0716 | 0.5876 | 0.118* | |
C31 | 0.53696 (14) | 0.6687 (2) | 0.60515 (11) | 0.0294 (4) | |
C32 | 0.43873 (16) | 0.7240 (3) | 0.58234 (13) | 0.0447 (6) | |
H19 | 0.4102 | 0.7532 | 0.5314 | 0.054* | |
C33 | 0.38283 (17) | 0.7360 (3) | 0.63451 (13) | 0.0460 (6) | |
H33 | 0.3171 | 0.7729 | 0.6185 | 0.055* | |
C34 | 0.42433 (16) | 0.6936 (3) | 0.70989 (12) | 0.0375 (5) | |
C35 | 0.52071 (18) | 0.6367 (3) | 0.73315 (13) | 0.0446 (6) | |
H35 | 0.5484 | 0.6059 | 0.7840 | 0.054* | |
C36 | 0.57651 (16) | 0.6253 (3) | 0.68124 (12) | 0.0401 (5) | |
H36 | 0.6420 | 0.5876 | 0.6977 | 0.048* | |
C37 | 0.3650 (2) | 0.7116 (4) | 0.76638 (15) | 0.0552 (7) | |
F31A | 0.2712 (4) | 0.7447 (19) | 0.7364 (3) | 0.120 (5) | 0.579 (19) |
F32A | 0.3654 (11) | 0.5891 (10) | 0.8068 (8) | 0.143 (6) | 0.579 (19) |
F33A | 0.3997 (8) | 0.8211 (16) | 0.8150 (7) | 0.142 (6) | 0.579 (19) |
F31B | 0.2894 (10) | 0.6221 (17) | 0.7546 (8) | 0.109 (7) | 0.421 (19) |
F32B | 0.4157 (6) | 0.689 (2) | 0.8372 (3) | 0.102 (6) | 0.421 (19) |
F33B | 0.3293 (14) | 0.8486 (10) | 0.7660 (10) | 0.120 (7) | 0.421 (19) |
S51 | 0.40470 (4) | 0.79046 (7) | 0.26402 (3) | 0.04040 (17) | |
O51 | 0.43430 (14) | 0.7467 (2) | 0.19768 (9) | 0.0603 (5) | |
O52 | 0.32052 (12) | 0.71828 (19) | 0.27996 (10) | 0.0542 (5) | |
C51 | 0.38223 (19) | 0.9882 (3) | 0.25797 (15) | 0.0562 (7) | |
H51A | 0.3247 | 1.0095 | 0.2150 | 0.084* | |
H51B | 0.4401 | 1.0402 | 0.2509 | 0.084* | |
H51C | 0.3696 | 1.0234 | 0.3046 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0276 (9) | 0.0379 (10) | 0.0354 (9) | 0.0034 (8) | 0.0130 (7) | −0.0004 (8) |
N2 | 0.0299 (9) | 0.0393 (10) | 0.0330 (9) | 0.0046 (8) | 0.0137 (7) | 0.0014 (8) |
C3 | 0.0292 (10) | 0.0278 (10) | 0.0318 (11) | 0.0004 (8) | 0.0107 (8) | −0.0014 (8) |
C3A | 0.0290 (10) | 0.0321 (11) | 0.0303 (10) | 0.0007 (9) | 0.0103 (8) | −0.0014 (9) |
C4 | 0.0335 (11) | 0.0458 (13) | 0.0314 (11) | 0.0052 (10) | 0.0115 (9) | 0.0029 (9) |
N5 | 0.0335 (10) | 0.0495 (12) | 0.0315 (10) | 0.0003 (8) | 0.0085 (8) | 0.0067 (8) |
C6 | 0.0425 (13) | 0.0543 (15) | 0.0402 (13) | −0.0027 (11) | 0.0185 (10) | 0.0090 (11) |
C7 | 0.0361 (12) | 0.0517 (14) | 0.0382 (12) | −0.0014 (11) | 0.0177 (10) | −0.0002 (11) |
C7A | 0.0331 (11) | 0.0341 (11) | 0.0302 (11) | −0.0012 (9) | 0.0108 (9) | −0.0030 (9) |
C17 | 0.0253 (10) | 0.0477 (13) | 0.0420 (12) | 0.0030 (10) | 0.0135 (9) | −0.0011 (10) |
C11 | 0.0245 (10) | 0.0472 (14) | 0.0373 (12) | 0.0056 (10) | 0.0056 (9) | −0.0071 (10) |
C12 | 0.0359 (12) | 0.0476 (14) | 0.0382 (12) | 0.0058 (11) | 0.0041 (10) | −0.0038 (11) |
C13 | 0.0444 (14) | 0.0435 (15) | 0.0582 (16) | 0.0070 (12) | −0.0051 (12) | −0.0065 (12) |
C14 | 0.0532 (17) | 0.0545 (18) | 0.090 (2) | 0.0176 (14) | 0.0040 (16) | −0.0264 (16) |
C15 | 0.0517 (17) | 0.081 (2) | 0.083 (2) | 0.0128 (16) | 0.0265 (15) | −0.0307 (18) |
C16 | 0.0378 (13) | 0.0697 (18) | 0.0546 (15) | 0.0042 (12) | 0.0189 (11) | −0.0131 (13) |
C18 | 0.089 (2) | 0.0484 (17) | 0.085 (2) | −0.0031 (16) | 0.0013 (18) | 0.0071 (15) |
C31 | 0.0307 (11) | 0.0292 (10) | 0.0309 (10) | −0.0009 (8) | 0.0131 (8) | −0.0023 (8) |
C32 | 0.0328 (12) | 0.0695 (17) | 0.0319 (12) | 0.0070 (11) | 0.0095 (9) | 0.0032 (11) |
C33 | 0.0315 (12) | 0.0662 (17) | 0.0444 (14) | 0.0044 (11) | 0.0174 (10) | −0.0034 (12) |
C34 | 0.0405 (12) | 0.0385 (13) | 0.0400 (12) | −0.0033 (10) | 0.0216 (10) | −0.0022 (10) |
C35 | 0.0543 (15) | 0.0486 (14) | 0.0352 (12) | 0.0073 (12) | 0.0195 (11) | 0.0085 (10) |
C36 | 0.0394 (12) | 0.0445 (13) | 0.0381 (12) | 0.0104 (10) | 0.0137 (10) | 0.0072 (10) |
C37 | 0.0575 (17) | 0.0675 (19) | 0.0504 (16) | 0.0015 (16) | 0.0314 (13) | −0.0003 (15) |
F31A | 0.051 (3) | 0.249 (15) | 0.073 (3) | 0.037 (5) | 0.040 (2) | 0.029 (5) |
F32A | 0.206 (13) | 0.130 (6) | 0.153 (11) | 0.059 (7) | 0.150 (11) | 0.079 (6) |
F33A | 0.136 (8) | 0.186 (11) | 0.139 (9) | −0.060 (7) | 0.099 (7) | −0.115 (8) |
F31B | 0.099 (9) | 0.144 (11) | 0.120 (9) | −0.068 (8) | 0.087 (8) | −0.048 (7) |
F32B | 0.079 (4) | 0.201 (16) | 0.033 (3) | 0.028 (7) | 0.029 (3) | 0.006 (5) |
F33B | 0.177 (15) | 0.071 (5) | 0.174 (13) | 0.046 (7) | 0.152 (12) | 0.027 (6) |
S51 | 0.0433 (3) | 0.0389 (3) | 0.0345 (3) | −0.0008 (3) | 0.0037 (2) | 0.0037 (2) |
O51 | 0.0725 (12) | 0.0735 (13) | 0.0317 (9) | 0.0111 (10) | 0.0095 (8) | −0.0011 (8) |
O52 | 0.0430 (9) | 0.0535 (10) | 0.0580 (11) | −0.0130 (8) | 0.0009 (8) | 0.0122 (8) |
C51 | 0.0569 (16) | 0.0429 (14) | 0.0644 (16) | 0.0032 (12) | 0.0099 (13) | 0.0096 (12) |
N1—N2 | 1.351 (2) | C15—C16 | 1.387 (4) |
N1—C7A | 1.355 (2) | C15—H15 | 0.9300 |
N1—C17 | 1.458 (2) | C16—H16 | 0.9300 |
N2—C3 | 1.341 (2) | C18—H18A | 0.9600 |
C3—C3A | 1.414 (3) | C18—H18B | 0.9600 |
C3—C31 | 1.474 (3) | C18—H18C | 0.9600 |
C3A—C7A | 1.368 (3) | C31—C36 | 1.382 (3) |
C3A—C4 | 1.501 (3) | C31—C32 | 1.390 (3) |
C4—N5 | 1.466 (3) | C32—C33 | 1.384 (3) |
C4—H4A | 0.9700 | C32—H19 | 0.9300 |
C4—H4B | 0.9700 | C33—C34 | 1.372 (3) |
N5—C6 | 1.471 (3) | C33—H33 | 0.9300 |
N5—S51 | 1.6311 (17) | C34—C35 | 1.373 (3) |
C6—C7 | 1.520 (3) | C34—C37 | 1.489 (3) |
C6—H6A | 0.9700 | C35—C36 | 1.378 (3) |
C6—H6B | 0.9700 | C35—H35 | 0.9300 |
C7—C7A | 1.480 (3) | C36—H36 | 0.9300 |
C7—H7A | 0.9700 | C37—F31B | 1.275 (6) |
C7—H7B | 0.9700 | C37—F32B | 1.289 (7) |
C17—C11 | 1.506 (3) | C37—F31A | 1.290 (5) |
C17—H17A | 0.9700 | C37—F33B | 1.291 (7) |
C17—H17B | 0.9700 | C37—F32A | 1.293 (5) |
C11—C12 | 1.382 (3) | C37—F33A | 1.294 (6) |
C11—C16 | 1.388 (3) | S51—O52 | 1.4237 (17) |
C12—C13 | 1.386 (3) | S51—O51 | 1.4255 (18) |
C12—H12 | 0.9300 | S51—C51 | 1.749 (2) |
C13—C14 | 1.388 (4) | C51—H51A | 0.9600 |
C13—C18 | 1.506 (4) | C51—H51B | 0.9600 |
C14—C15 | 1.369 (4) | C51—H51C | 0.9600 |
C14—H14 | 0.9300 | ||
N2—N1—C7A | 112.11 (15) | C14—C15—H15 | 119.8 |
N2—N1—C17 | 119.84 (16) | C16—C15—H15 | 119.8 |
C7A—N1—C17 | 128.05 (17) | C15—C16—C11 | 119.5 (3) |
C3—N2—N1 | 105.09 (15) | C15—C16—H16 | 120.3 |
N2—C3—C3A | 110.61 (17) | C11—C16—H16 | 120.3 |
N2—C3—C31 | 118.47 (17) | C13—C18—H18A | 109.5 |
C3A—C3—C31 | 130.88 (18) | C13—C18—H18B | 109.5 |
C7A—C3A—C3 | 105.18 (17) | H18A—C18—H18B | 109.5 |
C7A—C3A—C4 | 121.52 (18) | C13—C18—H18C | 109.5 |
C3—C3A—C4 | 133.30 (18) | H18A—C18—H18C | 109.5 |
N5—C4—C3A | 108.52 (16) | H18B—C18—H18C | 109.5 |
N5—C4—H4A | 110.0 | C36—C31—C32 | 117.93 (19) |
C3A—C4—H4A | 110.0 | C36—C31—C3 | 120.29 (18) |
N5—C4—H4B | 110.0 | C32—C31—C3 | 121.77 (18) |
C3A—C4—H4B | 110.0 | C33—C32—C31 | 120.9 (2) |
H4A—C4—H4B | 108.4 | C33—C32—H19 | 119.6 |
C4—N5—C6 | 115.83 (17) | C31—C32—H19 | 119.6 |
C4—N5—S51 | 117.84 (14) | C34—C33—C32 | 120.0 (2) |
C6—N5—S51 | 117.44 (14) | C34—C33—H33 | 120.0 |
N5—C6—C7 | 109.18 (18) | C32—C33—H33 | 120.0 |
N5—C6—H6A | 109.8 | C33—C34—C35 | 119.9 (2) |
C7—C6—H6A | 109.8 | C33—C34—C37 | 119.8 (2) |
N5—C6—H6B | 109.8 | C35—C34—C37 | 120.3 (2) |
C7—C6—H6B | 109.8 | C34—C35—C36 | 120.1 (2) |
H6A—C6—H6B | 108.3 | C34—C35—H35 | 120.0 |
C7A—C7—C6 | 107.69 (17) | C36—C35—H35 | 120.0 |
C7A—C7—H7A | 110.2 | C35—C36—C31 | 121.2 (2) |
C6—C7—H7A | 110.2 | C35—C36—H36 | 119.4 |
C7A—C7—H7B | 110.2 | C31—C36—H36 | 119.4 |
C6—C7—H7B | 110.2 | F31B—C37—F32B | 105.2 (6) |
H7A—C7—H7B | 108.5 | F31B—C37—F33B | 105.7 (6) |
N1—C7A—C3A | 107.02 (17) | F32B—C37—F33B | 104.2 (6) |
N1—C7A—C7 | 126.75 (18) | F31A—C37—F32A | 105.3 (5) |
C3A—C7A—C7 | 126.15 (19) | F31A—C37—F33A | 104.8 (5) |
N1—C17—C11 | 113.69 (17) | F32A—C37—F33A | 106.4 (5) |
N1—C17—H17A | 108.8 | F31B—C37—C34 | 114.0 (3) |
C11—C17—H17A | 108.8 | F32B—C37—C34 | 114.6 (4) |
N1—C17—H17B | 108.8 | F31A—C37—C34 | 114.9 (3) |
C11—C17—H17B | 108.8 | F33B—C37—C34 | 112.2 (3) |
H17A—C17—H17B | 107.7 | F32A—C37—C34 | 112.7 (3) |
C12—C11—C16 | 119.2 (2) | F33A—C37—C34 | 112.0 (3) |
C12—C11—C17 | 120.74 (19) | O52—S51—O51 | 119.96 (11) |
C16—C11—C17 | 120.1 (2) | O52—S51—N5 | 106.72 (9) |
C11—C12—C13 | 121.9 (2) | O51—S51—N5 | 106.70 (10) |
C11—C12—H12 | 119.1 | O52—S51—C51 | 107.87 (12) |
C13—C12—H12 | 119.1 | O51—S51—C51 | 107.40 (12) |
C12—C13—C14 | 117.8 (3) | N5—S51—C51 | 107.65 (11) |
C12—C13—C18 | 120.7 (3) | S51—C51—H51A | 109.5 |
C14—C13—C18 | 121.5 (3) | S51—C51—H51B | 109.5 |
C15—C14—C13 | 121.2 (3) | H51A—C51—H51B | 109.5 |
C15—C14—H14 | 119.4 | S51—C51—H51C | 109.5 |
C13—C14—H14 | 119.4 | H51A—C51—H51C | 109.5 |
C14—C15—C16 | 120.4 (3) | H51B—C51—H51C | 109.5 |
C7A—N1—N2—C3 | 0.0 (2) | C14—C15—C16—C11 | 1.2 (4) |
C17—N1—N2—C3 | 179.28 (17) | C12—C11—C16—C15 | −0.8 (3) |
N1—N2—C3—C3A | 0.2 (2) | C17—C11—C16—C15 | 178.4 (2) |
N1—N2—C3—C31 | −177.72 (17) | N2—C3—C31—C36 | 0.0 (3) |
N2—C3—C3A—C7A | −0.3 (2) | C3A—C3—C31—C36 | −177.4 (2) |
C31—C3—C3A—C7A | 177.3 (2) | N2—C3—C31—C32 | 178.9 (2) |
N2—C3—C3A—C4 | 179.7 (2) | C3A—C3—C31—C32 | 1.5 (3) |
C31—C3—C3A—C4 | −2.7 (4) | C36—C31—C32—C33 | 0.5 (3) |
C7A—C3A—C4—N5 | 9.7 (3) | C3—C31—C32—C33 | −178.4 (2) |
C3—C3A—C4—N5 | −170.3 (2) | C31—C32—C33—C34 | 0.2 (4) |
C3A—C4—N5—C6 | −45.2 (2) | C32—C33—C34—C35 | −1.1 (4) |
C3A—C4—N5—S51 | 168.19 (14) | C32—C33—C34—C37 | 178.0 (2) |
C4—N5—C6—C7 | 67.6 (2) | C33—C34—C35—C36 | 1.4 (4) |
S51—N5—C6—C7 | −145.72 (16) | C37—C34—C35—C36 | −177.8 (2) |
N5—C6—C7—C7A | −47.5 (2) | C34—C35—C36—C31 | −0.7 (4) |
N2—N1—C7A—C3A | −0.2 (2) | C32—C31—C36—C35 | −0.3 (3) |
C17—N1—C7A—C3A | −179.38 (19) | C3—C31—C36—C35 | 178.7 (2) |
N2—N1—C7A—C7 | 176.8 (2) | C33—C34—C37—F31B | 68.1 (11) |
C17—N1—C7A—C7 | −2.4 (3) | C35—C34—C37—F31B | −112.8 (11) |
C3—C3A—C7A—N1 | 0.3 (2) | C33—C34—C37—F32B | −170.6 (10) |
C4—C3A—C7A—N1 | −179.72 (18) | C35—C34—C37—F32B | 8.5 (11) |
C3—C3A—C7A—C7 | −176.7 (2) | C33—C34—C37—F31A | 10.4 (9) |
C4—C3A—C7A—C7 | 3.3 (3) | C35—C34—C37—F31A | −170.4 (9) |
C6—C7—C7A—N1 | −160.2 (2) | C33—C34—C37—F33B | −52.1 (12) |
C6—C7—C7A—C3A | 16.2 (3) | C35—C34—C37—F33B | 127.1 (11) |
N2—N1—C17—C11 | 89.5 (2) | C33—C34—C37—F32A | 131.1 (10) |
C7A—N1—C17—C11 | −91.3 (3) | C35—C34—C37—F32A | −49.8 (10) |
N1—C17—C11—C12 | −56.3 (3) | C33—C34—C37—F33A | −108.9 (9) |
N1—C17—C11—C16 | 124.5 (2) | C35—C34—C37—F33A | 70.2 (10) |
C16—C11—C12—C13 | −0.4 (3) | C4—N5—S51—O52 | −37.73 (19) |
C17—C11—C12—C13 | −179.62 (19) | C6—N5—S51—O52 | 176.24 (17) |
C11—C12—C13—C14 | 1.2 (3) | C4—N5—S51—O51 | −167.12 (16) |
C11—C12—C13—C18 | −177.3 (2) | C6—N5—S51—O51 | 46.85 (19) |
C12—C13—C14—C15 | −0.8 (4) | C4—N5—S51—C51 | 77.85 (19) |
C18—C13—C14—C15 | 177.7 (3) | C6—N5—S51—C51 | −68.2 (2) |
C13—C14—C15—C16 | −0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···O51i | 0.97 | 2.52 | 3.426 (3) | 155 |
C33—H33···Cg1ii | 0.93 | 2.70 | 3.488 (3) | 144 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1. |
(a) | Ring-puckering parameters | ||
Parameter | (I) | (II) | (III) |
Q | 0.481 (3) | 0.517 (3) | 0.498 (2) |
θ | 48.0 (4) | 50.4 (3) | 52.6 (2) |
φ | 322.9 (5) | 331.6 (5) | 322.4 (3) |
(b) | Torsion angles | ||
N2—N1—C17—C11 | -87.2 (3) | -105.1 (3) | 89.5 (2) |
N1—C17—C11—C12 | 58.1 (4) | 59.0 (4) | -56.3 (3) |
N2—C3—C31—C32 | 162.9 (3) | 164.3 (3) | 178.9 (2) |
C4—C5—S51—O51 | -171.2 (2) | 179.7 (2) | -167.12 (16) |
C4—C5—S51—O52 | -42.6 (3) | -51.9 (2) | -37.73 (19) |
C4—C5—S51—C51 | 73.2 (2) | 62.8 (3) | 77.85 (19) |
Ring-puckering angles are calculated for the atom sequence N5–C4–C3A–C7A–C7–C6) |
Compound | D—H···A | D—H | H···A | D···A | D—H···A | |
(I) | C6—H6···Cg2i | 0.97 | 2.76 | 3.694 (4) | 161 | |
C33—H33···Cg1i | 0.03 | 2.73 | 3.595 (3) | 154 | ||
C51—H51A···N2ii | 0.96 | 2.55 | 3.483 (4) | 165 | ||
(II) | C15—H15···O52iii | 0.93 | 2.44 | 3.339 (4) | 163 | |
C17—H17A···O51iv | 0.97 | 2.57 | 3.487 (4) | 158 | ||
(III) | C17—H17A···O51v | 0.97 | 2.52 | 3.426 (3) | 155 | |
C33—H33···Cg2i | 0.93 | 2.70 | 3.488 (3) | 144 |
Symmetry codes:
(i) -x+1, -y+1, -z+1;
(ii) x+1/2, -y+3/2, -z+1;
(iii) x, y-1, z;
(iv) -x+1, y-1/2, -z+3/2;
(v) x+1/2, -y+3/2, z+1/2. Cg1 and Cg2 represent the centroids of the C11–C16 and C31–C36 rings, respectively. |
C—Cl···Cg | C—Cl | Cl···Cg | C···Cg | C—Cl···Cg | |
C14—Cl14···Cg1i | 1.736 (4) | 3.839 (2) | 4.559 (4) | 103.13 (13) | |
C14—Cl14···Cg2ii | 1.736 (4) | 3.4292 (18) | 5.031 (4) | 152.23 (14) |
Symmetry codes:
(i) x-1, y, z;
(ii) x-1, y-1, z. Cg1 and Cg2 represent the centroids of the C11–C16 and C31–C36 rings, respectively. |