Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010775/vj1110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010775/vj11104sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010775/vj11105sup3.hkl |
CCDC references: 132382; 132383
For both compounds, data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990). Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993) for (4); SHELXL97 (Sheldrick, 1997) for (5). For both compounds, molecular graphics: NRCVAX (Gabe et al., 1989). Software used to prepare material for publication: SHELXL93 for (4); SHELXL97 for (5).
C17H20N8S4 | Dx = 1.465 Mg m−3 |
Mr = 464.65 | Melting point: 180 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.620 (2) Å | Cell parameters from 42 reflections |
b = 10.411 (2) Å | θ = 4.7–13.1° |
c = 26.813 (5) Å | µ = 0.47 mm−1 |
β = 97.92 (2)° | T = 293 K |
V = 2106.8 (8) Å3 | Rhombehedral, colourless |
Z = 4 | 0.5 × 0.5 × 0.5 mm |
F(000) = 968 |
Siemens P4 diffractometer | 2893 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω–scan | h = 0→9 |
Absorption correction: ψ scan (local program; Karcher, 1981) | k = 0→12 |
Tmin = 0.749, Tmax = 0.778 | l = −31→31 |
3697 measured reflections | 3 standard reflections every 97 reflections |
3697 independent reflections | intensity decay: nil |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.142 | Calculated w = 1/[σ2(Fo2) + (0.1195P)2 + 1.4563P] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max < 0.001 |
3684 reflections | Δρmax = 0.50 e Å−3 |
267 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL93 (Sheldrick, 1993), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0066 (12) |
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 on F2 for ALL reflections except for 13 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor(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. All the H atoms were placed in geometrical idealized positions and allowed to ride on their parent atoms, to which each was bonded for the final cycles of refinement. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6765 (3) | 0.7323 (2) | 0.27058 (10) | 0.0567 (6) | |
N2 | 0.6687 (3) | 0.6147 (2) | 0.24806 (9) | 0.0546 (6) | |
C3 | 0.6296 (4) | 0.5188 (3) | 0.27724 (11) | 0.0552 (7) | |
H3 | 0.6191 (4) | 0.4323 (3) | 0.26873 (11) | 0.066* | |
C3A | 0.6076 (4) | 0.5743 (3) | 0.32313 (11) | 0.0519 (6) | |
C4 | 0.5678 (4) | 0.5361 (3) | 0.37090 (11) | 0.0546 (7) | |
S4 | 0.52861 (13) | 0.37328 (8) | 0.38199 (3) | 0.0668 (3) | |
CS4 | 0.5173 (7) | 0.3728 (4) | 0.44831 (14) | 0.0915 (13) | |
HS4A | 0.476 (4) | 0.2907 (12) | 0.4580 (3) | 0.137* | |
HS4B | 0.437 (4) | 0.439 (2) | 0.4561 (2) | 0.137* | |
HS4C | 0.6330 (11) | 0.389 (3) | 0.46636 (14) | 0.137* | |
N5 | 0.5591 (4) | 0.6212 (3) | 0.40670 (9) | 0.0586 (6) | |
C6 | 0.5897 (4) | 0.7470 (3) | 0.39526 (12) | 0.0571 (7) | |
S6 | 0.57146 (15) | 0.84538 (9) | 0.44724 (3) | 0.0769 (3) | |
CS6 | 0.5919 (6) | 1.0034 (4) | 0.4224 (2) | 0.0850 (11) | |
HS6A | 0.7103 (13) | 1.0157 (11) | 0.4148 (11) | 0.128* | |
HS6B | 0.567 (4) | 1.0659 (4) | 0.4467 (5) | 0.128* | |
HS6C | 0.509 (3) | 1.0134 (11) | 0.3921 (7) | 0.128* | |
N7 | 0.6293 (3) | 0.7968 (2) | 0.35316 (9) | 0.0562 (6) | |
C7A | 0.6375 (4) | 0.7067 (3) | 0.31652 (11) | 0.0517 (6) | |
N1' | 0.3980 (3) | 0.5145 (2) | 0.11726 (9) | 0.0553 (6) | |
N2' | 0.4251 (4) | 0.5241 (3) | 0.06768 (9) | 0.0641 (7) | |
C3' | 0.4362 (5) | 0.4053 (3) | 0.05171 (11) | 0.0626 (8) | |
H3' | 0.4538 (5) | 0.3832 (3) | 0.01917 (11) | 0.075* | |
C3'A | 0.4178 (4) | 0.3152 (3) | 0.09027 (10) | 0.0522 (6) | |
C4' | 0.4195 (4) | 0.1828 (3) | 0.09828 (10) | 0.0505 (6) | |
S4' | 0.44824 (14) | 0.08063 (8) | 0.04922 (3) | 0.0700 (3) | |
CS4' | 0.4605 (6) | −0.0718 (3) | 0.07966 (14) | 0.0786 (10) | |
HS4D | 0.5710 (18) | −0.0788 (12) | 0.1015 (9) | 0.118* | |
HS4E | 0.453 (4) | −0.1387 (3) | 0.0548 (2) | 0.118* | |
HS4F | 0.364 (2) | −0.0802 (12) | 0.0991 (9) | 0.118* | |
N5' | 0.3991 (3) | 0.1360 (2) | 0.14339 (8) | 0.0519 (6) | |
C6' | 0.3743 (4) | 0.2208 (3) | 0.18009 (10) | 0.0506 (6) | |
S6' | 0.34088 (11) | 0.15980 (7) | 0.23887 (3) | 0.0592 (3) | |
CS6' | 0.3691 (5) | −0.0101 (3) | 0.23178 (13) | 0.0671 (8) | |
HS6D | 0.348 (4) | −0.0531 (4) | 0.2620 (4) | 0.101* | |
HS6E | 0.4878 (11) | −0.0275 (4) | 0.2255 (10) | 0.101* | |
HS6F | 0.287 (2) | −0.0407 (5) | 0.2040 (6) | 0.101* | |
N7' | 0.3715 (3) | 0.3477 (2) | 0.17775 (9) | 0.0521 (6) | |
C7'A | 0.3946 (4) | 0.3903 (3) | 0.13179 (10) | 0.0505 (6) | |
C8 | 0.7079 (4) | 0.6063 (3) | 0.19635 (11) | 0.0606 (7) | |
H8A | 0.7015 (4) | 0.5172 (3) | 0.18565 (11) | 0.073* | |
H8B | 0.8277 (4) | 0.6364 (3) | 0.19510 (11) | 0.073* | |
C9 | 0.5800 (4) | 0.6852 (3) | 0.16051 (11) | 0.0591 (7) | |
H9A | 0.5692 (4) | 0.7696 (3) | 0.17511 (11) | 0.071* | |
H9B | 0.6297 (4) | 0.6966 (3) | 0.12940 (11) | 0.071* | |
C10 | 0.3986 (4) | 0.6287 (3) | 0.14827 (12) | 0.0600 (8) | |
H10A | 0.3537 (4) | 0.6070 (3) | 0.17934 (12) | 0.072* | |
H10B | 0.3200 (4) | 0.6923 (3) | 0.13074 (12) | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.078 (2) | 0.0427 (12) | 0.0505 (13) | −0.0017 (11) | 0.0118 (11) | −0.0015 (10) |
N2 | 0.0745 (15) | 0.0433 (12) | 0.0470 (13) | 0.0038 (11) | 0.0115 (11) | −0.0036 (10) |
C3 | 0.073 (2) | 0.0432 (14) | 0.0488 (15) | 0.0018 (13) | 0.0060 (13) | −0.0006 (12) |
C3A | 0.063 (2) | 0.0458 (15) | 0.0463 (14) | 0.0005 (12) | 0.0051 (12) | 0.0002 (11) |
C4 | 0.063 (2) | 0.050 (2) | 0.050 (2) | −0.0019 (13) | 0.0050 (12) | 0.0020 (12) |
S4 | 0.0962 (6) | 0.0473 (5) | 0.0581 (5) | −0.0031 (4) | 0.0150 (4) | 0.0050 (3) |
CS4 | 0.142 (4) | 0.079 (3) | 0.055 (2) | −0.008 (2) | 0.016 (2) | 0.016 (2) |
N5 | 0.074 (2) | 0.0537 (14) | 0.0487 (13) | −0.0033 (12) | 0.0112 (11) | −0.0025 (11) |
C6 | 0.068 (2) | 0.052 (2) | 0.052 (2) | −0.0037 (13) | 0.0099 (13) | −0.0053 (13) |
S6 | 0.1145 (8) | 0.0630 (6) | 0.0581 (5) | −0.0143 (5) | 0.0293 (5) | −0.0147 (4) |
CS6 | 0.121 (3) | 0.056 (2) | 0.082 (2) | −0.009 (2) | 0.029 (2) | −0.014 (2) |
N7 | 0.0728 (15) | 0.0464 (13) | 0.0503 (13) | −0.0019 (11) | 0.0118 (11) | −0.0058 (11) |
C7A | 0.060 (2) | 0.0452 (15) | 0.0499 (15) | −0.0013 (12) | 0.0082 (12) | −0.0018 (12) |
N1' | 0.075 (2) | 0.0464 (13) | 0.0457 (12) | −0.0013 (11) | 0.0110 (11) | 0.0057 (10) |
N2' | 0.098 (2) | 0.0514 (14) | 0.0431 (13) | −0.0026 (13) | 0.0110 (13) | 0.0074 (11) |
C3' | 0.095 (2) | 0.054 (2) | 0.0391 (14) | −0.006 (2) | 0.0089 (14) | 0.0025 (12) |
C3'A | 0.070 (2) | 0.0463 (15) | 0.0404 (13) | −0.0007 (12) | 0.0081 (12) | 0.0034 (11) |
C4' | 0.066 (2) | 0.0481 (15) | 0.0384 (13) | −0.0036 (12) | 0.0094 (11) | 0.0003 (11) |
S4' | 0.1196 (8) | 0.0501 (5) | 0.0433 (4) | 0.0001 (4) | 0.0217 (4) | −0.0020 (3) |
CS4' | 0.123 (3) | 0.053 (2) | 0.066 (2) | 0.002 (2) | 0.034 (2) | 0.002 (2) |
N5' | 0.0686 (14) | 0.0491 (13) | 0.0392 (12) | −0.0038 (11) | 0.0117 (10) | 0.0003 (10) |
C6' | 0.0591 (15) | 0.051 (2) | 0.0419 (14) | −0.0044 (12) | 0.0099 (11) | 0.0046 (11) |
S6' | 0.0832 (5) | 0.0554 (5) | 0.0419 (4) | 0.0003 (4) | 0.0195 (3) | 0.0077 (3) |
CS6' | 0.093 (2) | 0.053 (2) | 0.059 (2) | −0.001 (2) | 0.022 (2) | 0.0131 (14) |
N7' | 0.0699 (15) | 0.0465 (13) | 0.0418 (12) | 0.0016 (11) | 0.0145 (10) | 0.0033 (9) |
C7'A | 0.064 (2) | 0.0465 (14) | 0.0411 (13) | 0.0025 (12) | 0.0066 (11) | 0.0034 (11) |
C8 | 0.079 (2) | 0.057 (2) | 0.047 (2) | 0.0041 (15) | 0.0140 (14) | −0.0043 (13) |
C9 | 0.092 (2) | 0.0400 (14) | 0.048 (2) | −0.0001 (14) | 0.0184 (14) | 0.0036 (12) |
C10 | 0.081 (2) | 0.046 (2) | 0.055 (2) | 0.0105 (14) | 0.0164 (14) | 0.0041 (13) |
N1—C7A | 1.333 (4) | C3'—C3'A | 1.417 (4) |
N1—N2 | 1.363 (3) | C3'—H3' | 0.93 |
N2—C3 | 1.327 (4) | C3'A—C4' | 1.395 (4) |
N2—C8 | 1.461 (4) | C3'A—C7'A | 1.391 (4) |
C3—C3A | 1.390 (4) | C4'—N5' | 1.333 (3) |
C3—H3 | 0.93 | C4'—S4' | 1.729 (3) |
C3A—C7A | 1.412 (4) | S4'—CS4' | 1.782 (4) |
C3A—C4 | 1.413 (4) | CS4'—HS4D | 0.96 |
C4—N5 | 1.315 (4) | CS4'—HS4E | 0.96 |
C4—S4 | 1.754 (3) | CS4'—HS4F | 0.96 |
S4—CS4 | 1.792 (4) | N5'—C6' | 1.355 (4) |
CS4—HS4A | 0.96 | C6'—N7' | 1.323 (4) |
CS4—HS4B | 0.96 | C6'—S6' | 1.750 (3) |
CS4—HS4C | 0.96 | S6'—CS6' | 1.795 (3) |
N5—C6 | 1.372 (4) | CS6'—HS6D | 0.96 |
C6—N7 | 1.314 (4) | CS6'—HS6E | 0.96 |
C6—S6 | 1.750 (3) | CS6'—HS6F | 0.96 |
S6—CS6 | 1.790 (4) | N7'—C7'A | 1.344 (3) |
CS6—HS6A | 0.96 | C8—C9 | 1.513 (4) |
CS6—HS6B | 0.96 | C8—H8A | 0.97 |
CS6—HS6C | 0.96 | C8—H8B | 0.97 |
N7—C7A | 1.366 (4) | C9—C10 | 1.496 (5) |
N1'—C7'A | 1.352 (4) | C9—H9A | 0.97 |
N1'—N2' | 1.377 (3) | C9—H9B | 0.97 |
N1'—C10 | 1.450 (4) | C10—H10A | 0.97 |
N2'—C3' | 1.315 (4) | C10—H10B | 0.97 |
C7A—N1—N2 | 103.2 (2) | C7'A—C3'A—C3' | 104.4 (3) |
C3—N2—N1 | 114.5 (2) | N5'—C4'—C3'A | 120.1 (3) |
C3—N2—C8 | 127.3 (2) | N5'—C4'—S4' | 120.5 (2) |
N1—N2—C8 | 118.2 (2) | C3'A—C4'—S4' | 119.4 (2) |
N2—C3—C3A | 105.9 (3) | C4'—S4'—CS4' | 101.8 (2) |
N2—C3—H3 | 127.1 (2) | S4'—CS4'—HS4D | 109.5 (2) |
C3A—C3—H3 | 127.1 (2) | S4'—CS4'—HS4E | 109.47 (12) |
C3—C3A—C7A | 104.7 (3) | HS4D—CS4'—HS4E | 109.5 |
C3—C3A—C4 | 138.8 (3) | S4'—CS4'—HS4F | 109.47 (13) |
C7A—C3A—C4 | 116.5 (3) | HS4D—CS4'—HS4F | 109.5 |
N5—C4—C3A | 120.7 (3) | HS4E—CS4'—HS4F | 109.5 |
N5—C4—S4 | 120.0 (2) | C4'—N5'—C6' | 117.8 (2) |
C3A—C4—S4 | 119.2 (2) | N7'—C6'—N5' | 128.3 (3) |
C4—S4—CS4 | 101.7 (2) | N7'—C6'—S6' | 113.7 (2) |
S4—CS4—HS4A | 109.47 (14) | N5'—C6'—S6' | 118.0 (2) |
S4—CS4—HS4B | 109.5 (2) | C6'—S6'—CS6' | 103.2 (2) |
HS4A—CS4—HS4B | 109.5 | S6'—CS6'—HS6D | 109.47 (11) |
S4—CS4—HS4C | 109.5 (2) | S6'—CS6'—HS6E | 109.47 (12) |
HS4A—CS4—HS4C | 109.5 | HS6D—CS6'—HS6E | 109.5 |
HS4B—CS4—HS4C | 109.5 | S6'—CS6'—HS6F | 109.47 (12) |
C4—N5—C6 | 116.9 (3) | HS6D—CS6'—HS6F | 109.5 |
N7—C6—N5 | 129.4 (3) | HS6E—CS6'—HS6F | 109.5 |
N7—C6—S6 | 120.4 (2) | C6'—N7'—C7'A | 111.7 (2) |
N5—C6—S6 | 110.2 (2) | N7'—C7'A—N1' | 126.2 (3) |
C6—S6—CS6 | 102.7 (2) | N7'—C7'A—C3'A | 126.5 (3) |
S6—CS6—HS6A | 109.5 (2) | N1'—C7'A—C3'A | 107.3 (2) |
S6—CS6—HS6B | 109.47 (13) | N2—C8—C9 | 111.8 (2) |
HS6A—CS6—HS6B | 109.5 | N2—C8—H8A | 109.2 (2) |
S6—CS6—HS6C | 109.47 (14) | C9—C8—H8A | 109.2 (2) |
HS6A—CS6—HS6C | 109.5 | N2—C8—H8B | 109.2 (2) |
HS6B—CS6—HS6C | 109.5 | C9—C8—H8B | 109.2 (2) |
C6—N7—C7A | 112.7 (3) | H8A—C8—H8B | 107.9 |
N1—C7A—N7 | 124.4 (3) | C10—C9—C8 | 114.9 (3) |
N1—C7A—C3A | 111.8 (2) | C10—C9—H9A | 108.6 (2) |
N7—C7A—C3A | 123.8 (3) | C8—C9—H9A | 108.6 (2) |
C7'A—N1'—N2' | 111.0 (2) | C10—C9—H9B | 108.6 (2) |
C7'A—N1'—C10 | 128.1 (2) | C8—C9—H9B | 108.6 (2) |
N2'—N1'—C10 | 120.4 (2) | H9A—C9—H9B | 107.5 |
C3'—N2'—N1' | 105.7 (2) | N1'—C10—C9 | 112.2 (3) |
N2'—C3'—C3'A | 111.6 (3) | N1'—C10—H10A | 109.2 (2) |
N2'—C3'—H3' | 124.2 (2) | C9—C10—H10A | 109.2 (2) |
C3'A—C3'—H3' | 124.2 (2) | N1'—C10—H10B | 109.2 (2) |
C4'—C3'A—C7'A | 115.6 (3) | C9—C10—H10B | 109.2 (2) |
C4'—C3'A—C3' | 140.1 (3) | H10A—C10—H10B | 107.9 |
C7A—N1—N2—C3 | −0.7 (3) | N2'—C3'—C3'A—C7'A | −0.1 (4) |
C7A—N1—N2—C8 | −179.1 (2) | C7'A—C3'A—C4'—N5' | 0.2 (4) |
N1—N2—C3—C3A | 0.4 (3) | C3'—C3'A—C4'—N5' | 178.6 (4) |
C8—N2—C3—C3A | 178.6 (3) | C7'A—C3'A—C4'—S4' | −179.8 (2) |
N2—C3—C3A—C7A | 0.1 (3) | C3'—C3'A—C4'—S4' | −1.3 (6) |
N2—C3—C3A—C4 | −179.3 (3) | N5'—C4'—S4'—CS4' | −5.0 (3) |
C3—C3A—C4—N5 | 179.6 (3) | C3'A—C4'—S4'—CS4' | 174.9 (3) |
C7A—C3A—C4—N5 | 0.3 (4) | C3'A—C4'—N5'—C6' | 1.0 (4) |
C3—C3A—C4—S4 | −0.8 (5) | S4'—C4'—N5'—C6' | −179.0 (2) |
C7A—C3A—C4—S4 | 179.9 (2) | C4'—N5'—C6'—N7' | −1.8 (4) |
N5—C4—S4—CS4 | −8.3 (3) | C4'—N5'—C6'—S6' | 178.1 (2) |
C3A—C4—S4—CS4 | 172.1 (3) | N7'—C6'—S6'—CS6' | −175.6 (2) |
C3A—C4—N5—C6 | 0.1 (4) | N5'—C6'—S6'—CS6' | 4.4 (3) |
S4—C4—N5—C6 | −179.4 (2) | N5'—C6'—N7'—C7'A | 1.0 (4) |
C4—N5—C6—N7 | −0.8 (5) | S6'—C6'—N7'—C7'A | −178.9 (2) |
C4—N5—C6—S6 | 179.8 (2) | C6'—N7'—C7'A—N1' | 179.8 (3) |
N7—C6—S6—CS6 | 6.5 (3) | C6'—N7'—C7'A—C3'A | 0.5 (4) |
N5—C6—S6—CS6 | −174.0 (2) | N2'—N1'—C7'A—N7' | 179.7 (3) |
N5—C6—N7—C7A | 0.9 (5) | C10—N1'—C7'A—N7' | 7.9 (5) |
S6—C6—N7—C7A | −179.8 (2) | N2'—N1'—C7'A—C3'A | −0.8 (3) |
N2—N1—C7A—N7 | 179.9 (3) | C10—N1'—C7'A—C3'A | −172.7 (3) |
N2—N1—C7A—C3A | 0.7 (3) | C4'—C3'A—C7'A—N7' | −1.0 (5) |
C6—N7—C7A—N1 | −179.5 (3) | C3'—C3'A—C7'A—N7' | −180.0 (3) |
C6—N7—C7A—C3A | −0.3 (4) | C4'—C3'A—C7'A—N1' | 179.5 (3) |
C3—C3A—C7A—N1 | −0.5 (3) | C3'—C3'A—C7'A—N1' | 0.5 (3) |
C4—C3A—C7A—N1 | 179.0 (3) | C3—N2—C8—C9 | 120.9 (3) |
C3—C3A—C7A—N7 | −179.7 (3) | N1—N2—C8—C9 | −60.9 (4) |
C4—C3A—C7A—N7 | −0.2 (4) | N2—C8—C9—C10 | −74.3 (3) |
C7'A—N1'—N2'—C3' | 0.7 (4) | C7'A—N1'—C10—C9 | 100.5 (4) |
C10—N1'—N2'—C3' | 173.3 (3) | N2'—N1'—C10—C9 | −70.6 (4) |
N1'—N2'—C3'—C3'A | −0.4 (4) | C8—C9—C10—N1' | −69.9 (3) |
N2'—C3'—C3'A—C4' | −178.7 (4) |
C18H22N8O2S2 | Dx = 1.423 Mg m−3 |
Mr = 446.56 | Melting point: 150 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 31.736 (7) Å | Cell parameters from 39 reflections |
b = 8.308 (2) Å | θ = 4.9–12.8° |
c = 17.467 (4) Å | µ = 0.29 mm−1 |
β = 115.12 (2)° | T = 293 K |
V = 4169.8 (17) Å3 | Trapezoidal, colourless |
Z = 8 | 0.8 × 0.6 × 0.5 mm |
F(000) = 1872 |
Siemens P4 diffractometer | 3189 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω–scan | h = 0→37 |
Absorption correction: ψ scan (local program; Karcher, 1981) | k = 0→9 |
Tmin = 0.772, Tmax = 0.835 | l = −20→18 |
3616 measured reflections | 3 standard reflections every 97 reflections |
3616 independent reflections | intensity decay: nil |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0685P)2 + 1.3387P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3616 reflections | Δρmax = 0.28 e Å−3 |
276 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0068 (5) |
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 | ||
N1 | 0.08564 (6) | 0.62969 (18) | −0.28542 (10) | 0.0591 (4) | |
N2 | 0.09756 (6) | 0.7441 (2) | −0.32902 (11) | 0.0705 (4) | |
C3 | 0.09214 (8) | 0.8831 (3) | −0.29923 (14) | 0.0688 (5) | |
H3 | 0.0979 | 0.9821 | −0.3177 | 0.083* | |
C3A | 0.07636 (6) | 0.8636 (2) | −0.23533 (12) | 0.0568 (4) | |
C4 | 0.06206 (6) | 0.9544 (2) | −0.18356 (12) | 0.0549 (4) | |
O4 | 0.06165 (5) | 1.11449 (15) | −0.19000 (10) | 0.0693 (4) | |
CO4 | 0.04383 (8) | 1.2044 (3) | −0.13974 (15) | 0.0752 (6) | |
HO4A | 0.0432 | 1.3168 | −0.1528 | 0.113* | |
HO4B | 0.0635 | 1.1877 | −0.0809 | 0.113* | |
HO4C | 0.0129 | 1.1686 | −0.1520 | 0.113* | |
N5 | 0.04876 (5) | 0.88416 (17) | −0.12953 (10) | 0.0551 (4) | |
C6 | 0.04910 (6) | 0.7220 (2) | −0.12731 (11) | 0.0542 (4) | |
S6 | 0.03384 (2) | 0.62550 (6) | −0.05308 (4) | 0.0699 (2) | |
CS6 | 0.01876 (9) | 0.7890 (3) | −0.00360 (16) | 0.0864 (7) | |
HS6A | 0.0093 | 0.7481 | 0.0381 | 0.130* | |
HS6B | −0.0064 | 0.8488 | −0.0454 | 0.130* | |
HS6C | 0.0452 | 0.8582 | 0.0232 | 0.130* | |
N7 | 0.05989 (5) | 0.62061 (18) | −0.17441 (10) | 0.0574 (4) | |
C7A | 0.07327 (6) | 0.6979 (2) | −0.22805 (11) | 0.0540 (4) | |
N1' | 0.21661 (5) | 0.19233 (19) | −0.16005 (9) | 0.0570 (4) | |
N2' | 0.22763 (6) | 0.0909 (2) | −0.21125 (10) | 0.0673 (4) | |
C3' | 0.22196 (7) | −0.0549 (3) | −0.18828 (12) | 0.0678 (5) | |
H3' | 0.2271 | −0.1484 | −0.2124 | 0.081* | |
C3'A | 0.20724 (6) | −0.0533 (2) | −0.12306 (11) | 0.0581 (4) | |
C4' | 0.19595 (7) | −0.1701 (2) | −0.07508 (12) | 0.0619 (5) | |
O4' | 0.19753 (6) | −0.31573 (18) | −0.07920 (11) | 0.0862 (5) | |
N5' | 0.18098 (5) | −0.09753 (18) | −0.01662 (9) | 0.0574 (4) | |
C5' | 0.17019 (9) | −0.2054 (3) | 0.03898 (15) | 0.0774 (6) | |
H5'1 | 0.1785 | −0.3136 | 0.0318 | 0.116* | |
H5'2 | 0.1375 | −0.2002 | 0.0248 | 0.116* | |
H5'3 | 0.1875 | −0.1729 | 0.0967 | 0.116* | |
C6' | 0.17761 (6) | 0.0666 (2) | −0.01024 (10) | 0.0511 (4) | |
S6' | 0.154665 (17) | 0.13194 (6) | 0.06014 (3) | 0.06088 (19) | |
CS6' | 0.15532 (8) | 0.3456 (3) | 0.04607 (14) | 0.0684 (5) | |
HS6D | 0.1412 | 0.3981 | 0.0784 | 0.103* | |
HS6E | 0.1382 | 0.3714 | −0.0127 | 0.103* | |
HS6F | 0.1869 | 0.3818 | 0.0650 | 0.103* | |
N7' | 0.18896 (5) | 0.17353 (18) | −0.05219 (9) | 0.0532 (3) | |
C7'A | 0.20397 (6) | 0.1076 (2) | −0.10772 (10) | 0.0519 (4) | |
C8 | 0.08687 (7) | 0.4594 (2) | −0.30225 (13) | 0.0657 (5) | |
H8A | 0.0862 | 0.4455 | −0.3579 | 0.079* | |
H8B | 0.0594 | 0.4080 | −0.3023 | 0.079* | |
C9 | 0.12961 (7) | 0.3788 (2) | −0.23766 (12) | 0.0611 (5) | |
H9A | 0.1258 | 0.2631 | −0.2446 | 0.073* | |
H9B | 0.1323 | 0.4052 | −0.1817 | 0.073* | |
C10 | 0.17456 (6) | 0.4267 (2) | −0.24342 (11) | 0.0597 (4) | |
H10A | 0.1744 | 0.3835 | −0.2951 | 0.072* | |
H10B | 0.1761 | 0.5431 | −0.2459 | 0.072* | |
C11 | 0.21670 (6) | 0.3659 (2) | −0.16919 (12) | 0.0587 (4) | |
H11A | 0.2444 | 0.3975 | −0.1758 | 0.070* | |
H11B | 0.2181 | 0.4160 | −0.1180 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0683 (9) | 0.0549 (9) | 0.0614 (9) | 0.0026 (7) | 0.0346 (7) | −0.0009 (7) |
N2 | 0.0866 (11) | 0.0689 (11) | 0.0694 (10) | 0.0038 (8) | 0.0460 (9) | 0.0066 (8) |
C3 | 0.0837 (13) | 0.0626 (12) | 0.0735 (12) | 0.0059 (9) | 0.0464 (11) | 0.0100 (9) |
C3A | 0.0581 (9) | 0.0518 (10) | 0.0639 (10) | 0.0047 (7) | 0.0292 (8) | 0.0068 (8) |
C4 | 0.0541 (9) | 0.0475 (10) | 0.0645 (10) | 0.0018 (7) | 0.0264 (8) | 0.0032 (7) |
O4 | 0.0872 (9) | 0.0456 (7) | 0.0887 (10) | 0.0050 (6) | 0.0504 (8) | 0.0072 (6) |
CO4 | 0.0965 (15) | 0.0497 (11) | 0.0857 (14) | 0.0093 (10) | 0.0446 (12) | −0.0030 (10) |
N5 | 0.0574 (8) | 0.0496 (8) | 0.0620 (9) | 0.0017 (6) | 0.0289 (7) | 0.0017 (6) |
C6 | 0.0540 (9) | 0.0504 (10) | 0.0604 (10) | −0.0001 (7) | 0.0265 (8) | 0.0011 (7) |
S6 | 0.0917 (4) | 0.0570 (3) | 0.0802 (4) | 0.0014 (2) | 0.0549 (3) | 0.0063 (2) |
CS6 | 0.1172 (18) | 0.0799 (15) | 0.0858 (14) | 0.0203 (13) | 0.0658 (14) | 0.0088 (12) |
N7 | 0.0645 (9) | 0.0490 (8) | 0.0650 (9) | −0.0012 (6) | 0.0335 (7) | −0.0003 (6) |
C7A | 0.0532 (9) | 0.0521 (10) | 0.0590 (9) | 0.0022 (7) | 0.0260 (7) | 0.0010 (7) |
N1' | 0.0695 (9) | 0.0587 (9) | 0.0528 (8) | 0.0089 (7) | 0.0356 (7) | −0.0018 (7) |
N2' | 0.0825 (10) | 0.0721 (11) | 0.0604 (9) | 0.0118 (8) | 0.0429 (8) | −0.0074 (8) |
C3' | 0.0805 (12) | 0.0679 (13) | 0.0613 (10) | 0.0129 (10) | 0.0362 (9) | −0.0135 (9) |
C3'A | 0.0671 (10) | 0.0550 (10) | 0.0530 (9) | 0.0097 (8) | 0.0262 (8) | −0.0061 (8) |
C4' | 0.0729 (11) | 0.0510 (11) | 0.0586 (10) | 0.0082 (8) | 0.0247 (9) | −0.0055 (8) |
O4' | 0.1227 (12) | 0.0478 (8) | 0.0925 (11) | 0.0073 (8) | 0.0500 (10) | −0.0075 (7) |
N5' | 0.0693 (9) | 0.0488 (8) | 0.0548 (8) | 0.0050 (6) | 0.0271 (7) | 0.0030 (6) |
C5' | 0.1006 (15) | 0.0556 (12) | 0.0846 (14) | 0.0015 (10) | 0.0477 (12) | 0.0127 (10) |
C6' | 0.0571 (9) | 0.0493 (9) | 0.0467 (8) | 0.0044 (7) | 0.0217 (7) | −0.0008 (7) |
S6' | 0.0752 (3) | 0.0635 (3) | 0.0556 (3) | 0.0044 (2) | 0.0389 (2) | 0.00198 (19) |
CS6' | 0.0860 (13) | 0.0624 (11) | 0.0710 (12) | 0.0039 (9) | 0.0471 (10) | −0.0100 (9) |
N7' | 0.0690 (8) | 0.0486 (8) | 0.0491 (7) | 0.0064 (6) | 0.0318 (6) | −0.0008 (6) |
C7'A | 0.0585 (9) | 0.0534 (10) | 0.0465 (8) | 0.0089 (7) | 0.0249 (7) | −0.0019 (7) |
C8 | 0.0713 (11) | 0.0605 (11) | 0.0701 (11) | −0.0038 (9) | 0.0347 (9) | −0.0120 (9) |
C9 | 0.0747 (11) | 0.0497 (10) | 0.0686 (11) | 0.0003 (8) | 0.0399 (9) | 0.0018 (8) |
C10 | 0.0731 (11) | 0.0551 (10) | 0.0593 (10) | 0.0006 (8) | 0.0360 (9) | 0.0023 (8) |
C11 | 0.0676 (10) | 0.0594 (11) | 0.0589 (10) | −0.0026 (8) | 0.0364 (9) | −0.0026 (8) |
N1—C7A | 1.347 (2) | N1'—C11 | 1.451 (2) |
N1—N2 | 1.368 (2) | N2'—C3' | 1.313 (3) |
N1—C8 | 1.449 (2) | C3'—C3'A | 1.403 (3) |
N2—C3 | 1.307 (3) | C3'A—C7'A | 1.375 (3) |
C3—C3A | 1.413 (3) | C3'A—C4' | 1.424 (3) |
C3A—C7A | 1.390 (3) | C4'—O4' | 1.214 (3) |
C3A—C4 | 1.393 (3) | C4'—N5' | 1.430 (2) |
C4—N5 | 1.322 (2) | N5'—C6' | 1.376 (2) |
C4—O4 | 1.334 (2) | N5'—C5' | 1.465 (3) |
O4—CO4 | 1.439 (2) | C6'—N7' | 1.296 (2) |
N5—C6 | 1.348 (2) | C6'—S6' | 1.7597 (17) |
C6—N7 | 1.320 (2) | S6'—CS6' | 1.794 (2) |
C6—S6 | 1.7582 (18) | N7'—C7'A | 1.364 (2) |
S6—CS6 | 1.781 (2) | C8—C9 | 1.504 (3) |
N7—C7A | 1.345 (2) | C9—C10 | 1.525 (2) |
N1'—C7'A | 1.343 (2) | C10—C11 | 1.501 (3) |
N1'—N2' | 1.378 (2) | ||
C7A—N1—N2 | 111.02 (14) | C3'—N2'—N1' | 105.11 (15) |
C7A—N1—C8 | 127.11 (16) | N2'—C3'—C3'A | 112.04 (17) |
N2—N1—C8 | 121.87 (16) | C7'A—C3'A—C3' | 104.26 (18) |
C3—N2—N1 | 106.13 (16) | C7'A—C3'A—C4' | 119.27 (16) |
N2—C3—C3A | 111.33 (18) | C3'—C3'A—C4' | 136.47 (18) |
C7A—C3A—C4 | 114.96 (16) | O4'—C4'—C3'A | 128.11 (19) |
C7A—C3A—C3 | 104.37 (17) | O4'—C4'—N5' | 119.82 (19) |
C4—C3A—C3 | 140.60 (18) | C3'A—C4'—N5' | 112.07 (16) |
N5—C4—O4 | 120.37 (16) | C6'—N5'—C4' | 122.45 (16) |
N5—C4—C3A | 120.99 (16) | C6'—N5'—C5' | 120.29 (16) |
O4—C4—C3A | 118.63 (16) | C4'—N5'—C5' | 117.24 (16) |
C4—O4—CO4 | 117.27 (15) | N7'—C6'—N5' | 125.72 (15) |
C4—N5—C6 | 117.44 (16) | N7'—C6'—S6' | 118.69 (13) |
N7—C6—N5 | 128.38 (16) | N5'—C6'—S6' | 115.58 (13) |
N7—C6—S6 | 113.22 (13) | C6'—S6'—CS6' | 100.22 (9) |
N5—C6—S6 | 118.40 (13) | C6'—N7'—C7'A | 113.03 (15) |
C6—S6—CS6 | 103.00 (10) | N1'—C7'A—N7' | 124.65 (16) |
C6—N7—C7A | 111.83 (15) | N1'—C7'A—C3'A | 107.94 (15) |
N7—C7A—N1 | 126.56 (16) | N7'—C7'A—C3'A | 127.37 (17) |
N7—C7A—C3A | 126.31 (17) | N1—C8—C9 | 112.09 (16) |
N1—C7A—C3A | 107.13 (15) | C8—C9—C10 | 113.92 (16) |
C7'A—N1'—N2' | 110.64 (15) | C11—C10—C9 | 111.76 (15) |
C7'A—N1'—C11 | 127.69 (14) | N1'—C11—C10 | 112.76 (15) |
N2'—N1'—C11 | 121.56 (15) | ||
C7A—N1—N2—C3 | −0.6 (2) | C7'A—C3'A—C4'—O4' | −178.8 (2) |
C8—N1—N2—C3 | 179.28 (18) | C3'—C3'A—C4'—O4' | 1.7 (4) |
N1—N2—C3—C3A | −0.2 (2) | C7'A—C3'A—C4'—N5' | 1.6 (2) |
N2—C3—C3A—C7A | 0.8 (2) | C3'—C3'A—C4'—N5' | −177.9 (2) |
N2—C3—C3A—C4 | −175.7 (2) | O4'—C4'—N5'—C6' | −178.70 (18) |
C7A—C3A—C4—N5 | 2.9 (2) | C3'A—C4'—N5'—C6' | 1.0 (2) |
C3—C3A—C4—N5 | 179.2 (2) | O4'—C4'—N5'—C5' | 2.8 (3) |
C7A—C3A—C4—O4 | −176.53 (16) | C3'A—C4'—N5'—C5' | −177.55 (16) |
C3—C3A—C4—O4 | −0.3 (4) | C4'—N5'—C6'—N7' | −3.0 (3) |
N5—C4—O4—CO4 | −3.4 (3) | C5'—N5'—C6'—N7' | 175.49 (17) |
C3A—C4—O4—CO4 | 176.02 (17) | C4'—N5'—C6'—S6' | 175.72 (13) |
O4—C4—N5—C6 | 178.70 (15) | C5'—N5'—C6'—S6' | −5.8 (2) |
C3A—C4—N5—C6 | −0.7 (2) | N7'—C6'—S6'—CS6' | 0.22 (16) |
C4—N5—C6—N7 | −2.1 (3) | N5'—C6'—S6'—CS6' | −178.56 (14) |
C4—N5—C6—S6 | 177.46 (12) | N5'—C6'—N7'—C7'A | 1.9 (2) |
N7—C6—S6—CS6 | −177.38 (14) | S6'—C6'—N7'—C7'A | −176.75 (11) |
N5—C6—S6—CS6 | 2.95 (17) | N2'—N1'—C7'A—N7' | −176.75 (15) |
N5—C6—N7—C7A | 2.2 (3) | C11—N1'—C7'A—N7' | −0.5 (3) |
S6—C6—N7—C7A | −177.39 (12) | N2'—N1'—C7'A—C3'A | 0.9 (2) |
C6—N7—C7A—N1 | −178.67 (16) | C11—N1'—C7'A—C3'A | 177.14 (16) |
C6—N7—C7A—C3A | 0.5 (3) | C6'—N7'—C7'A—N1' | 178.24 (15) |
N2—N1—C7A—N7 | −179.61 (16) | C6'—N7'—C7'A—C3'A | 1.0 (3) |
C8—N1—C7A—N7 | 0.5 (3) | C3'—C3'A—C7'A—N1' | −0.7 (2) |
N2—N1—C7A—C3A | 1.1 (2) | C4'—C3'A—C7'A—N1' | 179.58 (15) |
C8—N1—C7A—C3A | −178.75 (17) | C3'—C3'A—C7'A—N7' | 176.84 (17) |
C4—C3A—C7A—N7 | −2.9 (3) | C4'—C3'A—C7'A—N7' | −2.8 (3) |
C3—C3A—C7A—N7 | 179.58 (17) | C7A—N1—C8—C9 | −78.9 (2) |
C4—C3A—C7A—N1 | 176.40 (14) | N2—N1—C8—C9 | 101.3 (2) |
C3—C3A—C7A—N1 | −1.2 (2) | N1—C8—C9—C10 | −70.2 (2) |
C7'A—N1'—N2'—C3' | −0.7 (2) | C8—C9—C10—C11 | 170.26 (16) |
C11—N1'—N2'—C3' | −177.18 (16) | C7'A—N1'—C11—C10 | −99.0 (2) |
N1'—N2'—C3'—C3'A | 0.2 (2) | N2'—N1'—C11—C10 | 76.9 (2) |
N2'—C3'—C3'A—C7'A | 0.3 (2) | C9—C10—C11—N1' | 57.8 (2) |
N2'—C3'—C3'A—C4' | 179.9 (2) |
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