Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035677/ob2060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035677/ob2060Isup2.hkl |
CCDC reference: 624946
Data collection: MSC/AFC Diffractometer Control Software (Rigaku/MSC, 2000); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
C20H10N4O2·2C4H9NO | F(000) = 540.00 |
Mr = 512.56 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 16.129 (5) Å | θ = 10.5–13.2° |
b = 4.020 (5) Å | µ = 0.09 mm−1 |
c = 20.676 (6) Å | T = 296 K |
β = 105.18 (2)° | Platelet, orange |
V = 1293.8 (17) Å3 | 0.40 × 0.10 × 0.03 mm |
Z = 2 |
Rigaku AFC-7R diffractometer | Rint = 0.082 |
ω/2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→20 |
Tmin = 0.968, Tmax = 0.997 | k = −5→0 |
3078 measured reflections | l = −26→25 |
2975 independent reflections | 3 standard reflections every 0 reflections |
665 reflections with F2 > 2σ(F2) | intensity decay: 22.0% |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.109 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.347 | (Δ/σ)max < 0.001 |
S = 1.14 | Δρmax = 0.85 e Å−3 |
2975 reflections | Δρmin = −0.37 e Å−3 |
143 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Following bonds and angles of DMA were restrained: bond distances of C11—C12, C11—O2, C11—N3, N3—C13 and N3—C14, and bond angles of C11/N3/C13 and C13/N3/C14. The highest residual density peak of 0.85 e Å-3 was located 1.00 Å from atom N3. Refinement using reflections with F2 > 2 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5981 (3) | 0.3044 (16) | 0.6276 (2) | 0.0608 (18) | |
O2 | 0.7780 (3) | 0.6305 (17) | 0.5472 (3) | 0.0781 (19) | |
N1 | 0.6219 (3) | 0.2455 (16) | 0.5222 (2) | 0.0434 (18) | |
N2 | 0.8766 (4) | 0.525 (2) | 0.3587 (4) | 0.091 (3) | |
N3 | 0.8872 (6) | 0.884 (2) | 0.6079 (4) | 0.117 (3) | |
C1 | 0.6180 (4) | 0.127 (2) | 0.4033 (3) | 0.039 (2) | |
C2 | 0.6974 (4) | 0.259 (2) | 0.4072 (3) | 0.046 (2) | |
C3 | 0.7264 (4) | 0.274 (2) | 0.3508 (3) | 0.044 (2) | |
C4 | 0.6792 (5) | 0.159 (2) | 0.2897 (4) | 0.058 (2) | |
C5 | 0.6010 (5) | 0.020 (2) | 0.2856 (3) | 0.055 (2) | |
C6 | 0.5666 (4) | 0.003 (2) | 0.3410 (3) | 0.045 (2) | |
C7 | 0.5779 (4) | 0.109 (2) | 0.4604 (3) | 0.0365 (19) | |
C8 | 0.5028 (4) | −0.0263 (19) | 0.4668 (2) | 0.0328 (18) | |
C9 | 0.5737 (4) | 0.204 (2) | 0.5695 (3) | 0.041 (2) | |
C10 | 0.8114 (6) | 0.409 (2) | 0.3552 (4) | 0.064 (2) | |
C11 | 0.8172 (8) | 0.764 (3) | 0.6047 (6) | 0.123 (5) | |
C12 | 0.7842 (5) | 0.787 (2) | 0.6674 (4) | 0.081 (2) | |
C13 | 0.9418 (5) | 1.030 (2) | 0.6689 (4) | 0.079 (3) | |
C14 | 0.9180 (5) | 0.879 (2) | 0.5419 (4) | 0.090 (3) | |
H1N | 0.6712 | 0.3412 | 0.5302 | 0.052* | |
H2 | 0.7313 | 0.3378 | 0.4478 | 0.055* | |
H4 | 0.7002 | 0.1759 | 0.2520 | 0.070* | |
H5 | 0.5695 | −0.0669 | 0.2448 | 0.066* | |
H6 | 0.5123 | −0.0849 | 0.3373 | 0.054* | |
H12A | 0.8082 | 0.9790 | 0.6902 | 0.097* | |
H12B | 0.7250 | 0.7920 | 0.6536 | 0.097* | |
H12C | 0.8048 | 0.5937 | 0.6930 | 0.097* | |
H13A | 0.9301 | 1.2642 | 0.6698 | 0.098* | |
H13B | 1.0011 | 0.9980 | 0.6697 | 0.098* | |
H13C | 0.9302 | 0.9250 | 0.7073 | 0.098* | |
H14A | 0.9482 | 0.6755 | 0.5396 | 0.100* | |
H14B | 0.9555 | 1.0644 | 0.5419 | 0.100* | |
H14C | 0.8690 | 0.8944 | 0.5038 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.054 (3) | 0.089 (5) | 0.037 (3) | −0.022 (3) | 0.009 (2) | −0.014 (3) |
O2 | 0.07 (17) | 0.074 (6) | 0.074 (4) | 0.000 (4) | 0.000 (3) | 0.000 (4) |
N1 | 0.033 (3) | 0.065 (5) | 0.027 (3) | −0.006 (3) | −0.001 (2) | −0.010 (3) |
N2 | 0.053 (4) | 0.121 (8) | 0.104 (6) | −0.032 (5) | 0.030 (4) | 0.000 (6) |
N3 | 0.1 (3) | 0.112 (6) | 0.112 (13) | 0.000 (5) | 0.000 (7) | 0.000 (8) |
C1 | 0.037 (4) | 0.049 (5) | 0.031 (3) | 0.006 (4) | 0.010 (3) | 0.011 (3) |
C2 | 0.039 (4) | 0.058 (6) | 0.046 (4) | 0.006 (4) | 0.019 (3) | 0.007 (4) |
C3 | 0.032 (3) | 0.058 (6) | 0.043 (4) | −0.001 (4) | 0.014 (3) | 0.004 (4) |
C4 | 0.066 (5) | 0.071 (7) | 0.048 (5) | −0.006 (5) | 0.033 (4) | 0.005 (5) |
C5 | 0.057 (5) | 0.064 (6) | 0.045 (4) | −0.012 (5) | 0.016 (3) | 0.003 (5) |
C6 | 0.043 (4) | 0.052 (5) | 0.037 (4) | 0.000 (4) | 0.004 (3) | 0.000 (4) |
C7 | 0.031 (3) | 0.049 (5) | 0.030 (3) | −0.004 (4) | 0.010 (3) | 0.000 (3) |
C8 | 0.034 (3) | 0.041 (5) | 0.026 (3) | −0.012 (4) | 0.012 (3) | −0.006 (3) |
C9 | 0.040 (4) | 0.053 (6) | 0.028 (3) | −0.002 (4) | 0.008 (3) | 0.004 (4) |
C10 | 0.068 (5) | 0.075 (7) | 0.058 (5) | 0.000 (6) | 0.032 (4) | 0.009 (5) |
C11 | 0.1 (4) | 0.118 (8) | 0.118 (17) | 0.000 (7) | 0.000 (9) | 0.000 (9) |
C12 | 0.1 (2) | 0.077 (8) | 0.077 (7) | 0.000 (6) | 0.000 (6) | 0.000 (6) |
C13 | 0.1 (2) | 0.076 (7) | 0.076 (7) | 0.000 (5) | 0.000 (4) | 0.000 (6) |
C14 | 0.1 (2) | 0.086 (10) | 0.086 (7) | 0.000 (7) | 0.000 (6) | 0.000 (8) |
O1—C9 | 1.230 (8) | C4—C5 | 1.363 (12) |
O2—C11 | 1.307 (14) | C4—H4 | 0.930 |
N1—C7 | 1.400 (8) | C5—C6 | 1.398 (12) |
N1—C9 | 1.410 (10) | C5—H5 | 0.930 |
N1—H1N | 0.860 | C6—H6 | 0.930 |
N2—C10 | 1.136 (13) | C7—C8 | 1.365 (10) |
N3—C11 | 1.213 (17) | C8—C8i | 1.417 (9) |
N3—C13 | 1.460 (12) | C8—C9i | 1.452 (9) |
N3—C14 | 1.568 (15) | C11—C12 | 1.528 (18) |
C1—C2 | 1.370 (10) | C13—H13A | 0.960 |
C1—C6 | 1.426 (9) | C13—H13B | 0.960 |
C1—C7 | 1.490 (10) | C13—H13C | 0.960 |
C2—C3 | 1.365 (12) | C14—H14A | 0.960 |
C2—H2 | 0.930 | C14—H14B | 0.960 |
C3—C4 | 1.373 (10) | C14—H14C | 0.960 |
C3—C10 | 1.456 (13) | ||
O1···H4ii | 2.667 | H12A···H12C | 1.5514 |
O1···H5ii | 2.790 | H12A···H12Cviii | 2.4727 |
O1···H12B | 2.783 | H12A···H13A | 2.406 |
O2···H1N | 2.030 | H12A···H13C | 1.919 |
O2···H2 | 2.316 | H12B···O1 | 2.783 |
O2···H12B | 2.642 | H12B···O2 | 2.642 |
N3···H12A | 2.409 | H12B···C11 | 2.010 |
N3···H12C | 2.730 | H12B···C12 | 0.923 |
C11···H12A | 2.007 | H12B···H12A | 1.5514 |
C11···H12B | 2.010 | H12B···H12C | 1.5514 |
C11···H12C | 2.009 | H12C···N3 | 2.730 |
C12···H12A | 0.934 | H12C···C11 | 2.009 |
C12···H12B | 0.923 | H12C···C12 | 0.950 |
C12···H12C | 0.950 | H12C···H4ii | 2.567 |
C13···H12A | 2.319 | H12C···H12Aix | 2.4727 |
H1N···O2 | 2.030 | H12C···H12A | 1.5514 |
H2···O2 | 2.316 | H12C···H12B | 1.5514 |
H4···O1iii | 2.667 | H12C···H13Aix | 2.563 |
H4···H12Aiv | 2.785 | H12C···H13C | 2.375 |
H4···H12Ciii | 2.567 | H13A···H12A | 2.406 |
H5···O1iii | 2.790 | H13A···H12Cviii | 2.563 |
H5···H6v | 2.790 | H13A···H13Cviii | 2.767 |
H5···H6vi | 2.684 | H13C···H12A | 1.919 |
H6···H5v | 2.684 | H13C···H12C | 2.375 |
H6···H5vi | 2.790 | H13C···H13Aix | 2.767 |
H12A···N3 | 2.409 | H14A···H14Bix | 2.459 |
H12A···C11 | 2.007 | H14A···H14Bx | 2.779 |
H12A···C12 | 0.934 | H14B···H14Aviii | 2.459 |
H12A···C13 | 2.319 | H14B···H14Ax | 2.779 |
H12A···H4vii | 2.785 | H14B···H14Bx | 2.575 |
H12A···H12B | 1.5514 | ||
C7—N1—C9 | 110.3 (5) | C7—C8—C9i | 143.3 (6) |
C7—N1—H1N | 124.9 | C8i—C8—C9i | 108.2 (6) |
C9—N1—H1N | 124.9 | O1—C9—N1 | 123.0 (6) |
C11—N3—C13 | 123.3 (11) | O1—C9—C8i | 132.6 (7) |
C11—N3—C14 | 116.7 (9) | N1—C9—C8i | 104.4 (5) |
C13—N3—C14 | 120.0 (8) | N2—C10—C3 | 177.6 (11) |
C2—C1—C6 | 120.1 (7) | O2—C11—N3 | 115.8 (12) |
C2—C1—C7 | 124.4 (6) | O2—C11—C12 | 127.0 (11) |
C6—C1—C7 | 115.5 (6) | N3—C11—C12 | 117.1 (10) |
C1—C2—C3 | 119.4 (6) | C11—C12—H12A | 106.7 |
C1—C2—H2 | 120.3 | C11—C12—H12B | 107.6 |
C3—C2—H2 | 120.3 | C11—C12—H12C | 106.0 |
C2—C3—C4 | 122.7 (7) | H12A—C12—H12B | 113.3 |
C2—C3—C10 | 119.3 (6) | H12A—C12—H12C | 110.9 |
C4—C3—C10 | 118.0 (7) | H12B—C12—H12C | 111.9 |
C3—C4—C5 | 118.5 (8) | N3—C13—H13A | 109.5 |
C3—C4—H4 | 120.8 | N3—C13—H13B | 109.5 |
C5—C4—H4 | 120.8 | N3—C13—H13C | 109.5 |
C4—C5—C6 | 121.8 (7) | H13A—C13—H13B | 109.5 |
C4—C5—H5 | 119.1 | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 119.1 | H13B—C13—H13C | 109.5 |
C1—C6—C5 | 117.6 (6) | N3—C14—H14A | 109.5 |
C1—C6—H6 | 121.2 | N3—C14—H14B | 109.5 |
C5—C6—H6 | 121.2 | N3—C14—H14C | 109.5 |
N1—C7—C1 | 118.9 (5) | H14A—C14—H14B | 109.5 |
N1—C7—C8 | 108.6 (6) | H14A—C14—H14C | 109.5 |
C1—C7—C8 | 132.5 (6) | H14B—C14—H14C | 109.5 |
C7—C8—C8i | 108.5 (5) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x, −y+3/2, z−1/2; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) x, −y+3/2, z+1/2; (viii) x, y+1, z; (ix) x, y−1, z; (x) −x+2, −y+2, −z+1. |