Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503117X/lh6501sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680503117X/lh6501IIdsup2.hkl |
CCDC reference: 290311
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
C19H21N5O3S | Z = 2 |
Mr = 399.47 | F(000) = 420 |
Triclinic, P1 | Dx = 1.427 Mg m−3 |
Hall symbol: -P 1 | Melting point = 474–476 K |
a = 7.879 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.825 (2) Å | Cell parameters from 704 reflections |
c = 14.927 (3) Å | θ = 3.0–69.5° |
α = 99.94 (3)° | µ = 1.82 mm−1 |
β = 101.43 (3)° | T = 293 K |
γ = 109.04 (3)° | Prism, yellow |
V = 929.6 (5) Å3 | 0.35 × 0.25 × 0.15 mm |
Bruker SMART APEX CCD diffractometer | 3403 independent reflections |
Radiation source: fine-focus sealed tube | 3190 reflections with I > \2s(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 70.1°, θmin = 3.1° |
Absorption correction: multi-scan [SADABS (Sheldrick, 2002), based on the method of Blessing (1995)] | h = −8→9 |
Tmin = 0.633, Tmax = 0.764 | k = −10→10 |
10692 measured reflections | l = −18→18 |
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)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0961P)2 + 0.0935P] where P = (Fo2 + 2Fc2)/3 |
3403 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Experimental. Ratio of minimum to maximum apparent transmission: 0.827920 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.2084 (0.0044) x - 4.4754 (0.0047) y - 6.6599 (0.0097) z = 4.0244 (0.0028) * 0.0105 (0.0007) S1 * -0.0168 (0.0009) N2 * 0.0156 (0.0010) C3 * -0.0059 (0.0010) C9 * -0.0035 (0.0008) C8 0.0523 (0.0024) O3 0.2645 (0.0028) C12 Rms deviation of fitted atoms = 0.0117 7.0856 (0.0043) x - 4.6338 (0.0053) y - 6.8645 (0.0088) z = 4.0442 (0.0031) Angle to previous plane (with approximate e.s.d.) = 2.16 (0.08) * -0.0040 (0.0011) C4 * 0.0041 (0.0011) C5 * -0.0017 (0.0010) C6 * -0.0008 (0.0010) N7 * 0.0008 (0.0010) C8 * 0.0016 (0.0010) C9 - 0.0524 (0.0031) C10 - 0.0221 (0.0027) C11 Rms deviation of fitted atoms = 0.0026 7.1390 (0.0039) x - 4.5653 (0.0040) y - 6.7816 (0.0069) z = 4.0113 (0.0025) Angle to previous plane (with approximate e.s.d.) = 0.92 (0.07) * 0.0020 (0.0008) S1 * -0.0378 (0.0012) N2 * 0.0154 (0.0012) C3 * -0.0039 (0.0012) C4 * -0.0125 (0.0013) C5 * -0.0148 (0.0011) C6 * 0.0057 (0.0010) N7 * 0.0235 (0.0013) C8 * 0.0225 (0.0013) C9 - 0.0560 (0.0029) C10 - 0.0537 (0.0023) C11 0.2125 (0.0023) C12 0.0462 (0.0021) O3 Rms deviation of fitted atoms = 0.0187 7.3725 (0.0042) x - 2.7583 (0.0054) y + 2.2491 (0.0096) z = 5.0983 (0.0048) Angle to previous plane (with approximate e.s.d.) = 43.49 (0.04) * -0.0102 (0.0010) C31 * 0.0119 (0.0011) C32 * -0.0043 (0.0011) C33 * -0.0051 (0.0011) C34 * 0.0064 (0.0011) C35 * 0.0012 (0.0011) C36 - 0.0147 (0.0022) N37 - 0.1466 (0.0028) O38 0.1138 (0.0027) O39 Rms deviation of fitted atoms = 0.0075 7.6328 (0.0044) x - 3.2989 (0.0094) y + 0.7630 (0.0146) z = 4.8885 (0.0049) Angle to previous plane (with approximate e.s.d.) = 7.38 (0.08) * -0.0017 (0.0010) C22 * 0.0016 (0.0009) C23 * -0.0016 (0.0009) C25 * 0.0017 (0.0010) C26 0.7216 (0.0024) N21 - 0.4158 (0.0024) N24 Rms deviation of fitted atoms = 0.0016 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.48172 (6) | −0.18807 (5) | 0.04192 (3) | 0.07101 (19) | |
O3 | 0.4844 (2) | −0.45259 (17) | 0.21625 (9) | 0.0787 (4) | |
O38 | 0.8643 (3) | 1.01920 (16) | 0.61839 (10) | 0.0868 (4) | |
O39 | 0.8201 (2) | 0.89670 (17) | 0.72875 (9) | 0.0829 (4) | |
N2 | 0.5434 (2) | −0.23756 (18) | 0.14606 (11) | 0.0665 (4) | |
N7 | 0.20006 (19) | −0.42763 (16) | −0.09385 (9) | 0.0596 (3) | |
N21 | 0.7137 (2) | 0.01542 (17) | 0.27949 (10) | 0.0633 (3) | |
N24 | 0.67208 (17) | 0.28923 (15) | 0.38921 (9) | 0.0533 (3) | |
N37 | 0.8263 (2) | 0.89334 (18) | 0.64734 (10) | 0.0641 (3) | |
C3 | 0.4493 (2) | −0.3987 (2) | 0.14764 (11) | 0.0599 (4) | |
C4 | 0.1733 (3) | −0.64672 (19) | 0.02686 (11) | 0.0610 (4) | |
C5 | 0.0573 (3) | −0.6917 (2) | −0.06372 (12) | 0.0635 (4) | |
H51 | −0.046 (4) | −0.800 (3) | −0.0892 (17) | 0.095* | |
C6 | 0.0720 (2) | −0.5820 (2) | −0.12174 (11) | 0.0583 (4) | |
C8 | 0.3121 (2) | −0.38592 (19) | −0.00664 (11) | 0.0547 (3) | |
C9 | 0.3087 (2) | −0.48501 (18) | 0.05668 (11) | 0.0551 (4) | |
C10 | 0.1525 (4) | −0.7619 (2) | 0.09023 (15) | 0.0859 (6) | |
H101 | 0.2642 | −0.7849 | 0.1058 | 0.129* | |
H102 | 0.0484 | −0.8636 | 0.0584 | 0.129* | |
H103 | 0.1316 | −0.7112 | 0.1471 | 0.129* | |
C11 | −0.0579 (3) | −0.6328 (3) | −0.21856 (12) | 0.0729 (5) | |
H111 | −0.1101 | −0.5501 | −0.2264 | 0.109* | |
H112 | −0.1565 | −0.7370 | −0.2268 | 0.109* | |
H113 | 0.0093 | −0.6439 | −0.2648 | 0.109* | |
C12 | 0.7185 (3) | −0.1272 (2) | 0.21915 (15) | 0.0695 (4) | |
H121 | 0.752 (4) | −0.201 (3) | 0.2605 (19) | 0.104* | |
H122 | 0.803 (4) | −0.091 (3) | 0.1893 (19) | 0.104* | |
C22 | 0.5996 (3) | −0.0144 (2) | 0.34395 (14) | 0.0660 (4) | |
H221 | 0.461 (4) | −0.048 (3) | 0.3080 (18) | 0.099* | |
H222 | 0.615 (4) | −0.102 (3) | 0.3717 (19) | 0.099* | |
C23 | 0.6593 (3) | 0.1410 (2) | 0.42336 (12) | 0.0613 (4) | |
H231 | 0.787 (4) | 0.163 (3) | 0.4656 (18) | 0.092* | |
H232 | 0.572 (3) | 0.130 (3) | 0.4633 (17) | 0.092* | |
C25 | 0.7405 (3) | 0.3025 (2) | 0.30502 (12) | 0.0627 (4) | |
H251 | 0.692 (4) | 0.371 (3) | 0.2730 (18) | 0.094* | |
H252 | 0.878 (4) | 0.355 (3) | 0.3283 (18) | 0.094* | |
C26 | 0.6771 (3) | 0.1383 (2) | 0.23377 (13) | 0.0664 (4) | |
H261 | 0.540 (4) | 0.107 (3) | 0.2027 (18) | 0.100* | |
H262 | 0.751 (4) | 0.149 (3) | 0.1878 (19) | 0.100* | |
C31 | 0.71464 (19) | 0.43599 (18) | 0.45444 (10) | 0.0505 (3) | |
C32 | 0.6918 (2) | 0.4421 (2) | 0.54647 (11) | 0.0555 (3) | |
H321 | 0.648 (3) | 0.341 (3) | 0.5640 (16) | 0.083* | |
C33 | 0.7258 (2) | 0.5895 (2) | 0.60875 (11) | 0.0575 (4) | |
H331 | 0.695 (3) | 0.589 (3) | 0.6697 (17) | 0.086* | |
C34 | 0.7887 (2) | 0.73688 (19) | 0.58290 (10) | 0.0544 (3) | |
C35 | 0.8172 (2) | 0.7365 (2) | 0.49405 (11) | 0.0580 (4) | |
H351 | 0.868 (3) | 0.840 (3) | 0.4764 (17) | 0.087* | |
C36 | 0.7809 (2) | 0.59034 (19) | 0.43154 (11) | 0.0580 (4) | |
H361 | 0.803 (3) | 0.595 (3) | 0.3721 (17) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0749 (3) | 0.0545 (3) | 0.0736 (3) | 0.0146 (2) | 0.0094 (2) | 0.0229 (2) |
O3 | 0.0979 (10) | 0.0745 (8) | 0.0622 (7) | 0.0345 (7) | 0.0094 (6) | 0.0233 (6) |
O38 | 0.1266 (13) | 0.0600 (7) | 0.0732 (8) | 0.0360 (8) | 0.0223 (8) | 0.0188 (6) |
O39 | 0.1010 (10) | 0.0782 (8) | 0.0566 (7) | 0.0232 (7) | 0.0184 (6) | 0.0085 (6) |
N2 | 0.0693 (8) | 0.0560 (7) | 0.0657 (8) | 0.0212 (6) | 0.0055 (6) | 0.0135 (6) |
N7 | 0.0667 (8) | 0.0607 (7) | 0.0542 (7) | 0.0252 (6) | 0.0183 (6) | 0.0167 (6) |
N21 | 0.0628 (8) | 0.0572 (7) | 0.0685 (8) | 0.0249 (6) | 0.0129 (6) | 0.0133 (6) |
N24 | 0.0539 (7) | 0.0508 (6) | 0.0551 (7) | 0.0177 (5) | 0.0134 (5) | 0.0185 (5) |
N37 | 0.0641 (8) | 0.0650 (8) | 0.0560 (7) | 0.0218 (6) | 0.0076 (6) | 0.0116 (6) |
C3 | 0.0703 (9) | 0.0555 (8) | 0.0578 (8) | 0.0290 (7) | 0.0167 (7) | 0.0142 (6) |
C4 | 0.0791 (10) | 0.0499 (8) | 0.0574 (8) | 0.0246 (7) | 0.0251 (7) | 0.0139 (6) |
C5 | 0.0748 (10) | 0.0524 (8) | 0.0593 (8) | 0.0195 (7) | 0.0228 (7) | 0.0075 (7) |
C6 | 0.0646 (9) | 0.0592 (8) | 0.0535 (8) | 0.0255 (7) | 0.0219 (7) | 0.0093 (6) |
C8 | 0.0602 (8) | 0.0526 (8) | 0.0567 (8) | 0.0241 (6) | 0.0203 (6) | 0.0168 (6) |
C9 | 0.0669 (9) | 0.0513 (7) | 0.0532 (7) | 0.0268 (7) | 0.0211 (7) | 0.0139 (6) |
C10 | 0.1216 (18) | 0.0573 (10) | 0.0733 (11) | 0.0211 (10) | 0.0283 (11) | 0.0250 (8) |
C11 | 0.0767 (11) | 0.0777 (11) | 0.0568 (9) | 0.0262 (9) | 0.0144 (8) | 0.0084 (8) |
C12 | 0.0610 (9) | 0.0618 (10) | 0.0774 (11) | 0.0260 (8) | 0.0062 (8) | 0.0055 (8) |
C22 | 0.0689 (10) | 0.0527 (8) | 0.0747 (10) | 0.0200 (7) | 0.0165 (8) | 0.0209 (8) |
C23 | 0.0660 (9) | 0.0551 (8) | 0.0640 (9) | 0.0211 (7) | 0.0158 (7) | 0.0237 (7) |
C25 | 0.0742 (10) | 0.0567 (9) | 0.0587 (9) | 0.0225 (8) | 0.0216 (8) | 0.0183 (7) |
C26 | 0.0776 (11) | 0.0574 (9) | 0.0632 (9) | 0.0241 (8) | 0.0185 (8) | 0.0157 (7) |
C31 | 0.0426 (6) | 0.0546 (8) | 0.0525 (7) | 0.0166 (6) | 0.0083 (5) | 0.0178 (6) |
C32 | 0.0531 (8) | 0.0566 (8) | 0.0541 (8) | 0.0153 (6) | 0.0106 (6) | 0.0222 (6) |
C33 | 0.0529 (8) | 0.0667 (9) | 0.0488 (7) | 0.0186 (7) | 0.0083 (6) | 0.0185 (6) |
C34 | 0.0480 (7) | 0.0572 (8) | 0.0528 (8) | 0.0183 (6) | 0.0056 (6) | 0.0134 (6) |
C35 | 0.0584 (8) | 0.0551 (8) | 0.0586 (8) | 0.0175 (6) | 0.0136 (6) | 0.0201 (7) |
C36 | 0.0636 (9) | 0.0567 (8) | 0.0551 (8) | 0.0195 (7) | 0.0187 (7) | 0.0210 (7) |
S1—N2 | 1.7078 (16) | C10—H103 | 0.9600 |
S1—C8 | 1.7369 (18) | C11—H111 | 0.9600 |
O3—C3 | 1.222 (2) | C11—H112 | 0.9600 |
O38—N37 | 1.229 (2) | C11—H113 | 0.9600 |
O39—N37 | 1.2213 (19) | C12—H121 | 1.03 (3) |
N2—C3 | 1.380 (2) | C12—H122 | 0.88 (3) |
N2—C12 | 1.484 (2) | C22—C23 | 1.518 (3) |
N7—C8 | 1.333 (2) | C22—H221 | 1.04 (3) |
N7—C6 | 1.337 (2) | C22—H222 | 0.97 (3) |
N21—C12 | 1.432 (2) | C23—H231 | 1.02 (3) |
N21—C22 | 1.442 (2) | C23—H232 | 0.99 (2) |
N21—C26 | 1.451 (2) | C25—C26 | 1.505 (2) |
N24—C31 | 1.375 (2) | C25—H251 | 0.96 (3) |
N24—C23 | 1.465 (2) | C25—H252 | 0.99 (3) |
N24—C25 | 1.470 (2) | C26—H261 | 1.01 (3) |
N37—C34 | 1.443 (2) | C26—H262 | 0.98 (3) |
C3—C9 | 1.465 (2) | C31—C32 | 1.415 (2) |
C4—C5 | 1.382 (3) | C31—C36 | 1.419 (2) |
C4—C9 | 1.404 (2) | C32—C33 | 1.373 (2) |
C4—C10 | 1.497 (2) | C32—H321 | 0.95 (2) |
C5—C6 | 1.399 (2) | C33—C34 | 1.384 (2) |
C5—H51 | 0.98 (3) | C33—H331 | 0.99 (2) |
C6—C11 | 1.492 (3) | C34—C35 | 1.388 (2) |
C8—C9 | 1.392 (2) | C35—C36 | 1.361 (2) |
C10—H101 | 0.9600 | C35—H351 | 0.97 (3) |
C10—H102 | 0.9600 | C36—H361 | 0.94 (2) |
N2—S1—C8 | 90.62 (8) | N2—C12—H121 | 105.4 (15) |
C3—N2—C12 | 122.11 (16) | N21—C12—H122 | 107.0 (18) |
C3—N2—S1 | 115.84 (12) | N2—C12—H122 | 107.1 (18) |
C12—N2—S1 | 120.20 (13) | H121—C12—H122 | 112 (2) |
C8—N7—C6 | 115.06 (14) | N21—C22—C23 | 109.95 (14) |
C12—N21—C22 | 116.90 (15) | N21—C22—H221 | 109.7 (14) |
C12—N21—C26 | 116.25 (15) | C23—C22—H221 | 109.8 (14) |
C22—N21—C26 | 108.59 (14) | N21—C22—H222 | 110.0 (15) |
C31—N24—C23 | 118.29 (12) | C23—C22—H222 | 108.0 (16) |
C31—N24—C25 | 116.17 (12) | H221—C22—H222 | 109 (2) |
C23—N24—C25 | 117.30 (13) | N24—C23—C22 | 112.99 (14) |
O39—N37—O38 | 122.17 (15) | N24—C23—H231 | 107.1 (14) |
O39—N37—C34 | 119.13 (15) | C22—C23—H231 | 109.7 (14) |
O38—N37—C34 | 118.70 (13) | N24—C23—H232 | 107.2 (14) |
O3—C3—N2 | 122.74 (16) | C22—C23—H232 | 111.8 (14) |
O3—C3—C9 | 128.52 (16) | H231—C23—H232 | 107.7 (19) |
N2—C3—C9 | 108.74 (14) | N24—C25—C26 | 113.10 (14) |
C5—C4—C9 | 115.98 (15) | N24—C25—H251 | 109.6 (15) |
C5—C4—C10 | 121.97 (17) | C26—C25—H251 | 105.9 (15) |
C9—C4—C10 | 122.03 (17) | N24—C25—H252 | 106.2 (14) |
C4—C5—C6 | 122.03 (16) | C26—C25—H252 | 112.0 (14) |
C4—C5—H51 | 121.6 (14) | H251—C25—H252 | 110 (2) |
C6—C5—H51 | 116.2 (15) | N21—C26—C25 | 110.38 (15) |
N7—C6—C5 | 122.41 (16) | N21—C26—H261 | 112.7 (15) |
N7—C6—C11 | 116.70 (16) | C25—C26—H261 | 106.7 (15) |
C5—C6—C11 | 120.88 (16) | N21—C26—H262 | 105.5 (16) |
N7—C8—C9 | 127.05 (15) | C25—C26—H262 | 109.6 (15) |
N7—C8—S1 | 121.01 (12) | H261—C26—H262 | 112 (2) |
C9—C8—S1 | 111.91 (13) | N24—C31—C32 | 122.47 (13) |
C8—C9—C4 | 117.46 (15) | N24—C31—C36 | 121.06 (13) |
C8—C9—C3 | 112.81 (14) | C32—C31—C36 | 116.45 (14) |
C4—C9—C3 | 129.71 (15) | C33—C32—C31 | 121.46 (14) |
C4—C10—H101 | 109.5 | C33—C32—H321 | 120.0 (14) |
C4—C10—H102 | 109.5 | C31—C32—H321 | 118.5 (14) |
H101—C10—H102 | 109.5 | C32—C33—C34 | 119.98 (14) |
C4—C10—H103 | 109.5 | C32—C33—H331 | 119.6 (13) |
H101—C10—H103 | 109.5 | C34—C33—H331 | 120.2 (13) |
H102—C10—H103 | 109.5 | C35—C34—C33 | 120.29 (15) |
C6—C11—H111 | 109.5 | C35—C34—N37 | 118.76 (14) |
C6—C11—H112 | 109.5 | C33—C34—N37 | 120.96 (14) |
H111—C11—H112 | 109.5 | C36—C35—C34 | 119.92 (15) |
C6—C11—H113 | 109.5 | C36—C35—H351 | 119.0 (14) |
H111—C11—H113 | 109.5 | C34—C35—H351 | 121.0 (14) |
H112—C11—H113 | 109.5 | C35—C36—C31 | 121.87 (15) |
N21—C12—N2 | 117.34 (15) | C35—C36—H361 | 117.5 (14) |
N21—C12—H121 | 108.3 (15) | C31—C36—H361 | 120.6 (14) |
C8—S1—N2—C3 | 2.41 (13) | C3—N2—C12—N21 | −114.8 (2) |
C8—S1—N2—C12 | 167.25 (14) | S1—N2—C12—N21 | 81.3 (2) |
C12—N2—C3—O3 | 12.6 (3) | C12—N21—C22—C23 | 160.63 (15) |
S1—N2—C3—O3 | 177.15 (14) | C26—N21—C22—C23 | −65.43 (19) |
C12—N2—C3—C9 | −167.54 (15) | C31—N24—C23—C22 | 176.38 (13) |
S1—N2—C3—C9 | −3.01 (18) | C25—N24—C23—C22 | −36.3 (2) |
C9—C4—C5—C6 | −0.9 (2) | N21—C22—C23—N24 | 50.4 (2) |
C10—C4—C5—C6 | 177.53 (17) | C31—N24—C25—C26 | −175.91 (14) |
C8—N7—C6—C5 | −0.2 (2) | C23—N24—C25—C26 | 36.1 (2) |
C8—N7—C6—C11 | 179.20 (14) | C12—N21—C26—C25 | −160.35 (16) |
C4—C5—C6—N7 | 0.7 (2) | C22—N21—C26—C25 | 65.38 (19) |
C4—C5—C6—C11 | −178.68 (16) | N24—C25—C26—N21 | −49.7 (2) |
C6—N7—C8—C9 | 0.0 (2) | C23—N24—C31—C32 | −19.4 (2) |
C6—N7—C8—S1 | −178.10 (10) | C25—N24—C31—C32 | −167.05 (14) |
N2—S1—C8—N7 | 177.35 (13) | C23—N24—C31—C36 | 161.86 (15) |
N2—S1—C8—C9 | −1.00 (12) | C25—N24—C31—C36 | 14.2 (2) |
N7—C8—C9—C4 | −0.2 (2) | N24—C31—C32—C33 | −176.48 (13) |
S1—C8—C9—C4 | 178.03 (11) | C36—C31—C32—C33 | 2.3 (2) |
N7—C8—C9—C3 | −178.73 (14) | C31—C32—C33—C34 | −1.8 (2) |
S1—C8—C9—C3 | −0.49 (17) | C32—C33—C34—C35 | 0.2 (2) |
C5—C4—C9—C8 | 0.6 (2) | C32—C33—C34—N37 | −179.66 (13) |
C10—C4—C9—C8 | −177.80 (16) | O39—N37—C34—C35 | −172.54 (16) |
C5—C4—C9—C3 | 178.87 (15) | O38—N37—C34—C35 | 7.2 (2) |
C10—C4—C9—C3 | 0.4 (3) | O39—N37—C34—C33 | 7.3 (2) |
O3—C3—C9—C8 | −178.01 (17) | O38—N37—C34—C33 | −172.99 (16) |
N2—C3—C9—C8 | 2.17 (19) | C33—C34—C35—C36 | 0.8 (2) |
O3—C3—C9—C4 | 3.7 (3) | N37—C34—C35—C36 | −179.30 (14) |
N2—C3—C9—C4 | −176.13 (15) | C34—C35—C36—C31 | −0.3 (2) |
C22—N21—C12—N2 | 66.8 (2) | N24—C31—C36—C35 | 177.54 (14) |
C26—N21—C12—N2 | −63.6 (2) | C32—C31—C36—C35 | −1.3 (2) |