Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053943/xu2185sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053943/xu2185Isup2.hkl |
CCDC reference: 634084
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C13H12N4S | Z = 4 |
Mr = 256.33 | F(000) = 536 |
Triclinic, P1 | Dx = 1.335 Mg m−3 |
Hall symbol: -P 1 | Melting point = 441–443 K |
a = 8.7257 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3070 (2) Å | Cell parameters from 6212 reflections |
c = 14.4948 (6) Å | θ = 2.3–30.5° |
α = 83.828 (6)° | µ = 0.24 mm−1 |
β = 88.489 (6)° | T = 294 K |
γ = 79.757 (5)° | Block, purple |
V = 1275.35 (7) Å3 | 0.35 × 0.20 × 0.15 mm |
Rigaku R-AXIS RAPID-S diffractometer | 7756 independent reflections |
Radiation source: fine-focus sealed tube | 4027 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
ω scans | θmax = 30.6°, θmin = 2.3° |
Absorption correction: multi-scan (Blessing, 1995) | h = −12→12 |
Tmin = 0.920, Tmax = 0.965 | k = −14→14 |
38418 measured reflections | l = −20→20 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0774P)2 + 0.1466P] where P = (Fo2 + 2Fc2)/3 |
7756 reflections | (Δ/σ)max < 0.001 |
340 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.96406 (8) | 0.57516 (7) | 0.24474 (5) | 0.0699 (2) | |
N1 | 1.1582 (3) | 0.1463 (2) | −0.02977 (14) | 0.0668 (5) | |
N2 | 0.9849 (2) | 0.40115 (19) | 0.10280 (14) | 0.0612 (5) | |
N3 | 0.8438 (2) | 0.46420 (19) | 0.10351 (14) | 0.0613 (5) | |
N4 | 0.6863 (2) | 0.6288 (2) | 0.17971 (15) | 0.0685 (6) | |
C1 | 0.8212 (3) | 0.5538 (2) | 0.16932 (16) | 0.0581 (6) | |
C2 | 0.8306 (3) | 0.6918 (3) | 0.29243 (19) | 0.0694 (7) | |
H2 | 0.8505 | 0.7382 | 0.3411 | 0.083* | |
C3 | 0.6935 (3) | 0.7070 (3) | 0.25006 (18) | 0.0687 (7) | |
H3 | 0.6076 | 0.7671 | 0.2672 | 0.082* | |
C4 | 1.0133 (3) | 0.3086 (2) | 0.04167 (16) | 0.0586 (6) | |
C5 | 1.1618 (3) | 0.2332 (2) | 0.03396 (17) | 0.0654 (6) | |
C6 | 1.0089 (3) | 0.1634 (2) | −0.06575 (16) | 0.0639 (6) | |
C7 | 0.9529 (4) | 0.0962 (3) | −0.13190 (18) | 0.0815 (8) | |
H7 | 1.0159 | 0.0267 | −0.1579 | 0.098* | |
C8 | 0.8014 (4) | 0.1369 (4) | −0.1569 (2) | 0.0932 (10) | |
H8 | 0.7602 | 0.0937 | −0.2009 | 0.112* | |
C9 | 0.7062 (4) | 0.2410 (3) | −0.1187 (2) | 0.0901 (9) | |
H9 | 0.6042 | 0.2675 | −0.1390 | 0.108* | |
C10 | 0.7601 (3) | 0.3052 (3) | −0.05147 (19) | 0.0736 (7) | |
H10 | 0.6951 | 0.3734 | −0.0253 | 0.088* | |
C11 | 0.9144 (3) | 0.2659 (2) | −0.02323 (16) | 0.0616 (6) | |
C12 | 1.2892 (4) | 0.0504 (3) | −0.0590 (2) | 0.0891 (9) | |
H12A | 1.3848 | 0.0725 | −0.0396 | 0.134* | |
H12B | 1.2894 | 0.0522 | −0.1254 | 0.134* | |
H12C | 1.2797 | −0.0368 | −0.0313 | 0.134* | |
C13 | 1.3058 (3) | 0.2446 (3) | 0.0817 (2) | 0.0915 (9) | |
H13A | 1.3438 | 0.1626 | 0.1186 | 0.137* | |
H13B | 1.2838 | 0.3148 | 0.1211 | 0.137* | |
H13C | 1.3832 | 0.2636 | 0.0365 | 0.137* | |
S1' | 0.84660 (8) | 1.07021 (7) | 0.36197 (5) | 0.0727 (2) | |
N1' | 0.5552 (3) | 0.6425 (2) | 0.60720 (15) | 0.0683 (6) | |
N2' | 0.6524 (2) | 0.89819 (19) | 0.44770 (14) | 0.0594 (5) | |
N3' | 0.5796 (2) | 0.96062 (19) | 0.37586 (14) | 0.0608 (5) | |
N4' | 0.6070 (3) | 1.1267 (2) | 0.25554 (15) | 0.0719 (6) | |
C1' | 0.6638 (3) | 1.0512 (2) | 0.32932 (17) | 0.0606 (6) | |
C2' | 0.8455 (4) | 1.1884 (3) | 0.27023 (19) | 0.0763 (8) | |
H2' | 0.9262 | 1.2351 | 0.2553 | 0.092* | |
C3' | 0.7139 (4) | 1.2048 (3) | 0.2229 (2) | 0.0792 (8) | |
H3' | 0.6949 | 1.2657 | 0.1705 | 0.095* | |
C4' | 0.5798 (3) | 0.8046 (2) | 0.49534 (17) | 0.0577 (6) | |
C5' | 0.6465 (3) | 0.7310 (2) | 0.57498 (18) | 0.0651 (6) | |
C6' | 0.4258 (3) | 0.6585 (2) | 0.55006 (18) | 0.0654 (6) | |
C7' | 0.3023 (4) | 0.5905 (3) | 0.5569 (2) | 0.0844 (9) | |
H7' | 0.2978 | 0.5210 | 0.6029 | 0.101* | |
C8' | 0.1861 (4) | 0.6307 (4) | 0.4921 (3) | 0.1000 (11) | |
H8' | 0.1011 | 0.5873 | 0.4947 | 0.120* | |
C9' | 0.1921 (4) | 0.7342 (4) | 0.4229 (2) | 0.0965 (10) | |
H9' | 0.1103 | 0.7599 | 0.3812 | 0.116* | |
C10' | 0.3168 (3) | 0.7990 (3) | 0.4152 (2) | 0.0766 (7) | |
H10' | 0.3215 | 0.8672 | 0.3682 | 0.092* | |
C11' | 0.4360 (3) | 0.7603 (2) | 0.47935 (17) | 0.0612 (6) | |
C12' | 0.5824 (5) | 0.5473 (4) | 0.6895 (3) | 0.0933 (11) | |
H12F | 0.504 (4) | 0.553 (3) | 0.730 (3) | 0.115 (13)* | |
H12E | 0.597 (6) | 0.463 (6) | 0.669 (3) | 0.20 (2)* | |
H12D | 0.669 (6) | 0.562 (5) | 0.726 (3) | 0.18 (2)* | |
C13' | 0.7894 (4) | 0.7458 (3) | 0.6223 (2) | 0.0913 (9) | |
H13D | 0.7633 | 0.7712 | 0.6834 | 0.137* | |
H13E | 0.8369 | 0.8128 | 0.5873 | 0.137* | |
H13F | 0.8609 | 0.6631 | 0.6269 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0620 (4) | 0.0703 (4) | 0.0764 (5) | −0.0075 (3) | −0.0028 (3) | −0.0097 (3) |
N1 | 0.0744 (14) | 0.0599 (12) | 0.0604 (12) | −0.0007 (10) | 0.0071 (10) | −0.0015 (10) |
N2 | 0.0688 (13) | 0.0514 (11) | 0.0613 (12) | −0.0094 (9) | 0.0053 (9) | 0.0005 (9) |
N3 | 0.0697 (13) | 0.0527 (11) | 0.0599 (12) | −0.0091 (9) | 0.0024 (9) | −0.0028 (9) |
N4 | 0.0624 (13) | 0.0662 (13) | 0.0761 (14) | −0.0063 (10) | −0.0007 (10) | −0.0121 (11) |
C1 | 0.0612 (14) | 0.0511 (12) | 0.0605 (14) | −0.0115 (10) | 0.0028 (11) | 0.0023 (11) |
C2 | 0.0705 (17) | 0.0644 (15) | 0.0748 (17) | −0.0122 (12) | 0.0032 (13) | −0.0146 (13) |
C3 | 0.0649 (16) | 0.0665 (15) | 0.0743 (17) | −0.0075 (12) | 0.0057 (13) | −0.0133 (13) |
C4 | 0.0648 (14) | 0.0543 (13) | 0.0539 (13) | −0.0075 (11) | 0.0015 (11) | 0.0018 (10) |
C5 | 0.0706 (16) | 0.0627 (15) | 0.0594 (14) | −0.0068 (12) | 0.0007 (12) | 0.0006 (12) |
C6 | 0.0800 (17) | 0.0568 (14) | 0.0522 (13) | −0.0116 (12) | 0.0016 (12) | 0.0044 (11) |
C7 | 0.113 (2) | 0.0747 (18) | 0.0574 (16) | −0.0163 (17) | 0.0017 (16) | −0.0105 (13) |
C8 | 0.118 (3) | 0.102 (2) | 0.0666 (18) | −0.035 (2) | −0.0178 (18) | −0.0074 (17) |
C9 | 0.094 (2) | 0.099 (2) | 0.076 (2) | −0.0186 (19) | −0.0199 (17) | 0.0024 (18) |
C10 | 0.0750 (17) | 0.0755 (17) | 0.0672 (16) | −0.0096 (14) | −0.0052 (13) | 0.0018 (13) |
C11 | 0.0729 (16) | 0.0515 (12) | 0.0570 (14) | −0.0086 (11) | 0.0002 (11) | 0.0057 (11) |
C12 | 0.090 (2) | 0.0783 (19) | 0.087 (2) | 0.0145 (16) | 0.0141 (16) | −0.0106 (16) |
C13 | 0.0701 (18) | 0.107 (2) | 0.096 (2) | −0.0071 (17) | −0.0093 (16) | −0.0126 (19) |
S1' | 0.0759 (5) | 0.0714 (4) | 0.0718 (4) | −0.0204 (3) | 0.0029 (3) | −0.0004 (3) |
N1' | 0.0703 (14) | 0.0601 (12) | 0.0702 (14) | −0.0089 (10) | 0.0091 (11) | 0.0056 (10) |
N2' | 0.0658 (12) | 0.0533 (11) | 0.0587 (12) | −0.0111 (9) | 0.0054 (9) | −0.0048 (9) |
N3' | 0.0697 (13) | 0.0564 (11) | 0.0562 (11) | −0.0122 (9) | 0.0072 (10) | −0.0054 (9) |
N4' | 0.0858 (15) | 0.0668 (13) | 0.0617 (13) | −0.0152 (11) | 0.0014 (11) | 0.0011 (11) |
C1' | 0.0729 (16) | 0.0541 (13) | 0.0549 (13) | −0.0120 (11) | 0.0062 (11) | −0.0068 (11) |
C2' | 0.092 (2) | 0.0706 (17) | 0.0691 (17) | −0.0272 (15) | 0.0143 (15) | −0.0039 (13) |
C3' | 0.106 (2) | 0.0663 (16) | 0.0645 (17) | −0.0200 (16) | 0.0098 (16) | 0.0048 (13) |
C4' | 0.0604 (14) | 0.0529 (12) | 0.0592 (14) | −0.0106 (10) | 0.0045 (11) | −0.0037 (11) |
C5' | 0.0609 (15) | 0.0578 (14) | 0.0731 (16) | −0.0049 (11) | 0.0077 (12) | −0.0027 (12) |
C6' | 0.0704 (16) | 0.0550 (13) | 0.0728 (16) | −0.0148 (12) | 0.0141 (13) | −0.0125 (12) |
C7' | 0.090 (2) | 0.0730 (18) | 0.097 (2) | −0.0318 (16) | 0.0233 (18) | −0.0161 (16) |
C8' | 0.081 (2) | 0.111 (3) | 0.125 (3) | −0.049 (2) | 0.012 (2) | −0.036 (2) |
C9' | 0.082 (2) | 0.120 (3) | 0.096 (2) | −0.039 (2) | −0.0092 (17) | −0.014 (2) |
C10' | 0.0760 (18) | 0.087 (2) | 0.0714 (17) | −0.0244 (15) | −0.0032 (14) | −0.0123 (15) |
C11' | 0.0663 (15) | 0.0582 (13) | 0.0606 (14) | −0.0132 (11) | 0.0085 (11) | −0.0115 (11) |
C12' | 0.102 (3) | 0.083 (2) | 0.083 (2) | −0.006 (2) | 0.015 (2) | 0.0276 (19) |
C13' | 0.0770 (19) | 0.103 (2) | 0.090 (2) | −0.0188 (17) | −0.0164 (16) | 0.0159 (18) |
S1—C2 | 1.708 (3) | S1'—C2' | 1.703 (3) |
S1—C1 | 1.737 (2) | S1'—C1' | 1.725 (3) |
N1—C5 | 1.359 (3) | N1'—C5' | 1.353 (3) |
N1—C6 | 1.391 (3) | N1'—C6' | 1.393 (3) |
N1—C12 | 1.459 (3) | N1'—C12' | 1.457 (4) |
N2—N3 | 1.286 (3) | N2'—C4' | 1.364 (3) |
N2—C4 | 1.358 (3) | N3'—N2' | 1.284 (3) |
N3—C1 | 1.384 (3) | N3'—C1' | 1.396 (3) |
N4—C1 | 1.303 (3) | N4'—C3' | 1.380 (3) |
N4—C3 | 1.375 (3) | C1'—N4' | 1.307 (3) |
C2—H2 | 0.9300 | C2'—H2' | 0.9300 |
C3—C2 | 1.336 (3) | C3'—C2' | 1.329 (4) |
C3—H3 | 0.9300 | C3'—H3' | 0.9300 |
C4—C5 | 1.396 (3) | C4'—C5' | 1.392 (3) |
C4—C11 | 1.446 (3) | C4'—C11' | 1.441 (3) |
C6—C7 | 1.388 (4) | C5'—C13' | 1.478 (4) |
C7—C8 | 1.360 (4) | C6'—C7' | 1.383 (4) |
C7—H7 | 0.9300 | C7'—C8' | 1.378 (4) |
C8—H8 | 0.9300 | C7'—H7' | 0.9300 |
C9—C8 | 1.391 (5) | C8'—C9' | 1.391 (5) |
C9—H9 | 0.9300 | C8'—H8' | 0.9300 |
C10—C9 | 1.371 (4) | C9'—H9' | 0.9300 |
C10—H10 | 0.9300 | C10'—C9' | 1.371 (4) |
C11—C10 | 1.394 (4) | C10'—H10' | 0.9300 |
C11—C6 | 1.407 (3) | C11'—C10' | 1.389 (4) |
C12—H12A | 0.9600 | C11'—C6' | 1.399 (3) |
C12—H12B | 0.9600 | C12'—H12F | 0.89 (4) |
C12—H12C | 0.9600 | C12'—H12E | 0.94 (5) |
C13—C5 | 1.478 (4) | C12'—H12D | 0.98 (5) |
C13—H13A | 0.9600 | C13'—H13D | 0.9600 |
C13—H13B | 0.9600 | C13'—H13E | 0.9600 |
C13—H13C | 0.9600 | C13'—H13F | 0.9600 |
C2—S1—C1 | 88.76 (12) | C2'—S1'—C1' | 88.38 (14) |
C5—N1—C6 | 109.7 (2) | C5'—N1'—C6' | 109.0 (2) |
C5—N1—C12 | 126.4 (2) | C5'—N1'—C12' | 126.6 (3) |
C6—N1—C12 | 123.9 (2) | C6'—N1'—C12' | 124.4 (3) |
N3—N2—C4 | 114.8 (2) | N3'—N2'—C4' | 115.0 (2) |
N2—N3—C1 | 111.9 (2) | N2'—N3'—C1' | 111.4 (2) |
C1—N4—C3 | 109.9 (2) | C1'—N4'—C3' | 108.6 (2) |
N4—C1—N3 | 121.2 (2) | N4'—C1'—N3' | 120.5 (2) |
N4—C1—S1 | 114.59 (19) | N4'—C1'—S1' | 115.64 (19) |
N3—C1—S1 | 124.25 (18) | N3'—C1'—S1' | 123.81 (18) |
C3—C2—S1 | 110.5 (2) | C3'—C2'—S1' | 110.9 (2) |
C3—C2—H2 | 124.8 | C3'—C2'—H2' | 124.5 |
S1—C2—H2 | 124.8 | S1'—C2'—H2' | 124.5 |
C2—C3—N4 | 116.3 (2) | C2'—C3'—N4' | 116.4 (3) |
C2—C3—H3 | 121.9 | C2'—C3'—H3' | 121.8 |
N4—C3—H3 | 121.9 | N4'—C3'—H3' | 121.8 |
N2—C4—C5 | 120.5 (2) | N2'—C4'—C5' | 120.4 (2) |
N2—C4—C11 | 132.2 (2) | N2'—C4'—C11' | 131.9 (2) |
C5—C4—C11 | 107.3 (2) | C5'—C4'—C11' | 107.7 (2) |
N1—C5—C4 | 108.8 (2) | N1'—C5'—C4' | 109.0 (2) |
N1—C5—C13 | 123.0 (2) | N1'—C5'—C13' | 123.2 (2) |
C4—C5—C13 | 128.1 (3) | C4'—C5'—C13' | 127.8 (2) |
C7—C6—N1 | 129.2 (3) | C7'—C6'—N1' | 129.0 (3) |
C7—C6—C11 | 122.6 (3) | C7'—C6'—C11' | 122.1 (3) |
N1—C6—C11 | 108.2 (2) | N1'—C6'—C11' | 108.9 (2) |
C8—C7—C6 | 116.8 (3) | C8'—C7'—C6' | 116.6 (3) |
C8—C7—H7 | 121.6 | C8'—C7'—H7' | 121.7 |
C6—C7—H7 | 121.6 | C6'—C7'—H7' | 121.7 |
C7—C8—C9 | 122.1 (3) | C7'—C8'—C9' | 122.0 (3) |
C7—C8—H8 | 119.0 | C7'—C8'—H8' | 119.0 |
C9—C8—H8 | 119.0 | C9'—C8'—H8' | 119.0 |
C10—C9—C8 | 121.2 (3) | C10'—C9'—C8' | 120.9 (3) |
C10—C9—H9 | 119.4 | C10'—C9'—H9' | 119.5 |
C8—C9—H9 | 119.4 | C8'—C9'—H9' | 119.5 |
C9—C10—C11 | 118.6 (3) | C9'—C10'—C11' | 118.3 (3) |
C9—C10—H10 | 120.7 | C9'—C10'—H10' | 120.8 |
C11—C10—H10 | 120.7 | C11'—C10'—H10' | 120.8 |
C10—C11—C6 | 118.7 (2) | C10'—C11'—C6' | 119.9 (2) |
C10—C11—C4 | 135.4 (2) | C10'—C11'—C4' | 134.6 (2) |
C6—C11—C4 | 106.0 (2) | C6'—C11'—C4' | 105.4 (2) |
N1—C12—H12A | 109.5 | N1'—C12'—H12F | 114 (2) |
N1—C12—H12B | 109.5 | N1'—C12'—H12E | 106 (3) |
H12A—C12—H12B | 109.5 | H12F—C12'—H12E | 109 (4) |
N1—C12—H12C | 109.5 | N1'—C12'—H12D | 112 (3) |
H12A—C12—H12C | 109.5 | H12F—C12'—H12D | 102 (3) |
H12B—C12—H12C | 109.5 | H12E—C12'—H12D | 114 (4) |
C5—C13—H13A | 109.5 | C5'—C13'—H13D | 109.5 |
C5—C13—H13B | 109.5 | C5'—C13'—H13E | 109.5 |
H13A—C13—H13B | 109.5 | H13D—C13'—H13E | 109.5 |
C5—C13—H13C | 109.5 | C5'—C13'—H13F | 109.5 |
H13A—C13—H13C | 109.5 | H13D—C13'—H13F | 109.5 |
H13B—C13—H13C | 109.5 | H13E—C13'—H13F | 109.5 |
C1—S1—C2—C3 | −0.3 (2) | C1'—S1'—C2'—C3' | −0.2 (2) |
C2—S1—C1—N4 | 0.3 (2) | C2'—S1'—C1'—N4' | 0.3 (2) |
C2—S1—C1—N3 | −178.9 (2) | C2'—S1'—C1'—N3' | 179.2 (2) |
C6—N1—C5—C4 | 0.6 (3) | C6'—N1'—C5'—C4' | −1.1 (3) |
C12—N1—C5—C4 | 179.5 (2) | C12'—N1'—C5'—C4' | −179.4 (3) |
C6—N1—C5—C13 | −177.0 (2) | C6'—N1'—C5'—C13' | 176.6 (2) |
C12—N1—C5—C13 | 1.8 (4) | C12'—N1'—C5'—C13' | −1.7 (5) |
C5—N1—C6—C7 | −179.8 (3) | C5'—N1'—C6'—C7' | −179.6 (3) |
C12—N1—C6—C7 | 1.3 (4) | C12'—N1'—C6'—C7' | −1.2 (5) |
C5—N1—C6—C11 | 0.3 (3) | C5'—N1'—C6'—C11' | 0.1 (3) |
C12—N1—C6—C11 | −178.6 (2) | C12'—N1'—C6'—C11' | 178.5 (3) |
C4—N2—N3—C1 | 177.99 (18) | N3'—N2'—C4'—C5' | −179.5 (2) |
N3—N2—C4—C5 | 179.9 (2) | N3'—N2'—C4'—C11' | 1.1 (4) |
N3—N2—C4—C11 | −0.5 (4) | C1'—N3'—N2'—C4' | −177.96 (19) |
N2—N3—C1—N4 | 178.9 (2) | N2'—N3'—C1'—N4' | −178.3 (2) |
N2—N3—C1—S1 | −2.0 (3) | N2'—N3'—C1'—S1' | 2.8 (3) |
C3—N4—C1—N3 | 179.0 (2) | C1'—N4'—C3'—C2' | 0.0 (3) |
C3—N4—C1—S1 | −0.1 (3) | N3'—C1'—N4'—C3' | −179.2 (2) |
C1—N4—C3—C2 | −0.1 (3) | S1'—C1'—N4'—C3' | −0.2 (3) |
N4—C3—C2—S1 | 0.3 (3) | N4'—C3'—C2'—S1' | 0.2 (3) |
N2—C4—C5—N1 | 178.4 (2) | N2'—C4'—C11'—C10' | −4.1 (5) |
C11—C4—C5—N1 | −1.2 (3) | C5'—C4'—C11'—C10' | 176.4 (3) |
N2—C4—C5—C13 | −4.1 (4) | N2'—C4'—C11'—C6' | 178.0 (2) |
C11—C4—C5—C13 | 176.2 (3) | C5'—C4'—C11'—C6' | −1.5 (3) |
N2—C4—C11—C10 | 4.0 (5) | N2'—C4'—C5'—N1' | −177.9 (2) |
C5—C4—C11—C10 | −176.4 (3) | C11'—C4'—C5'—N1' | 1.6 (3) |
N2—C4—C11—C6 | −178.3 (2) | N2'—C4'—C5'—C13' | 4.5 (4) |
C5—C4—C11—C6 | 1.4 (3) | C11'—C4'—C5'—C13' | −176.0 (3) |
N1—C6—C7—C8 | −177.7 (3) | N1'—C6'—C7'—C8' | 177.6 (3) |
C11—C6—C7—C8 | 2.2 (4) | C11'—C6'—C7'—C8' | −2.0 (4) |
C6—C7—C8—C9 | 0.2 (5) | C6'—C7'—C8'—C9' | 0.1 (5) |
C10—C9—C8—C7 | −2.0 (5) | C7'—C8'—C9'—C10' | 1.5 (5) |
C11—C10—C9—C8 | 1.4 (4) | C11'—C10'—C9'—C8' | −1.2 (5) |
C10—C11—C6—C7 | −2.7 (4) | C10'—C11'—C6'—C7' | 2.3 (4) |
C4—C11—C6—C7 | 179.1 (2) | C4'—C11'—C6'—C7' | −179.4 (2) |
C10—C11—C6—N1 | 177.2 (2) | C10'—C11'—C6'—N1' | −177.4 (2) |
C4—C11—C6—N1 | −1.0 (3) | C4'—C11'—C6'—N1' | 0.9 (3) |
C6—C11—C10—C9 | 0.9 (4) | C6'—C11'—C10'—C9' | −0.7 (4) |
C4—C11—C10—C9 | 178.4 (3) | C4'—C11'—C10'—C9' | −178.3 (3) |