Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026371/ob6573sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026371/ob6573Isup2.hkl |
CCDC reference: 283976
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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.
C24H12N4O4·2C3H7NO | F(000) = 592.00 |
Mr = 566.57 | Dx = 1.432 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 8845 reflections |
a = 5.3890 (8) Å | θ = 3.6–68.1° |
b = 12.2012 (17) Å | µ = 0.85 mm−1 |
c = 19.998 (3) Å | T = 93 K |
β = 91.764 (10)° | Needle, gold |
V = 1314.3 (3) Å3 | 0.50 × 0.10 × 0.05 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 1357 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.048 |
48 frames, δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −5→5 |
Tmin = 0.625, Tmax = 0.958 | k = −14→14 |
12221 measured reflections | l = −23→23 |
2241 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.097 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.309 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 1.05 e Å−3 |
2241 reflections | Δρmin = −0.73 e Å−3 |
187 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 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 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8901 (5) | 0.4101 (2) | 0.32327 (14) | 0.0348 (8) | |
O2 | 0.2194 (5) | 0.2211 (2) | 0.40543 (13) | 0.0372 (8) | |
O3 | 0.3096 (12) | 0.8096 (6) | 0.5022 (4) | 0.145 (2) | |
N1 | 0.5484 (6) | 0.3191 (2) | 0.36374 (16) | 0.0290 (9) | |
N2 | 0.5910 (7) | 0.1097 (3) | 0.1952 (2) | 0.0419 (11) | |
N3 | 0.2190 (16) | 0.9075 (4) | 0.4086 (3) | 0.106 (2) | |
C1 | 0.5104 (8) | 0.4627 (3) | 0.47284 (19) | 0.0269 (10) | |
C2 | 0.7067 (7) | 0.4776 (3) | 0.42396 (19) | 0.0261 (10) | |
C3 | 0.7295 (8) | 0.4028 (3) | 0.3666 (2) | 0.0277 (10) | |
C4 | 0.3577 (8) | 0.3006 (3) | 0.4109 (2) | 0.0298 (10) | |
C5 | 0.3383 (8) | 0.3776 (3) | 0.4673 (2) | 0.0276 (10) | |
C6 | 0.1485 (8) | 0.3652 (3) | 0.5156 (2) | 0.0289 (10) | |
C7 | 0.8745 (7) | 0.5610 (3) | 0.4311 (2) | 0.0274 (10) | |
C8 | 0.5640 (8) | 0.2468 (3) | 0.3062 (2) | 0.0301 (11) | |
C9 | 0.7571 (9) | 0.1726 (4) | 0.2988 (2) | 0.0380 (12) | |
C10 | 0.7602 (9) | 0.1067 (4) | 0.2427 (2) | 0.0429 (13) | |
C11 | 0.4106 (9) | 0.1811 (4) | 0.2036 (2) | 0.0397 (12) | |
C12 | 0.3832 (8) | 0.2526 (3) | 0.2583 (2) | 0.0348 (11) | |
C13 | 0.335 (2) | 0.8703 (13) | 0.4547 (5) | 0.191 (4) | |
C14 | 0.2989 (16) | 0.9523 (6) | 0.3489 (3) | 0.091 (2) | |
C15 | −0.040 (2) | 0.8639 (13) | 0.3950 (5) | 0.191 (4) | |
H6 | 0.0357 | 0.3056 | 0.5113 | 0.035* | |
H7 | 1.0047 | 0.5689 | 0.4004 | 0.033* | |
H9 | 0.8860 | 0.1673 | 0.3322 | 0.046* | |
H11 | 0.2857 | 0.1847 | 0.1691 | 0.048* | |
H10 | 0.8935 | 0.0564 | 0.2387 | 0.052* | |
H12 | 0.2467 | 0.3015 | 0.2612 | 0.042* | |
H13 | 0.5013 | 0.8962 | 0.4542 | 0.230* | |
H14A | 0.4800 | 0.9601 | 0.3510 | 0.137* | |
H14B | 0.2224 | 1.0244 | 0.3419 | 0.137* | |
H14C | 0.2506 | 0.9039 | 0.3116 | 0.137* | |
H15A | −0.0330 | 0.7844 | 0.3883 | 0.287* | |
H15B | −0.1117 | 0.8988 | 0.3547 | 0.287* | |
H15C | −0.1436 | 0.8803 | 0.4332 | 0.287* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.030 (2) | 0.0408 (19) | 0.0335 (17) | −0.0023 (14) | 0.0031 (13) | −0.0024 (14) |
O2 | 0.040 (2) | 0.0406 (19) | 0.0309 (17) | −0.0119 (15) | −0.0049 (14) | −0.0049 (14) |
O3 | 0.107 (5) | 0.135 (5) | 0.190 (7) | −0.002 (4) | −0.039 (5) | 0.000 (5) |
N1 | 0.029 (2) | 0.033 (2) | 0.0250 (19) | −0.0042 (16) | −0.0043 (15) | −0.0021 (15) |
N2 | 0.036 (2) | 0.051 (2) | 0.038 (2) | −0.0011 (19) | −0.0018 (18) | −0.0133 (19) |
N3 | 0.161 (8) | 0.053 (3) | 0.104 (5) | −0.008 (4) | 0.003 (5) | 0.033 (3) |
C1 | 0.025 (2) | 0.034 (2) | 0.022 (2) | 0.0057 (18) | −0.0077 (17) | 0.0031 (17) |
C2 | 0.023 (2) | 0.033 (2) | 0.022 (2) | 0.0005 (17) | −0.0062 (16) | 0.0053 (17) |
C3 | 0.021 (2) | 0.036 (2) | 0.026 (2) | 0.0027 (19) | −0.0060 (17) | 0.0007 (18) |
C4 | 0.024 (2) | 0.042 (2) | 0.024 (2) | −0.0016 (19) | −0.0077 (17) | −0.0002 (18) |
C5 | 0.023 (2) | 0.032 (2) | 0.027 (2) | −0.0020 (18) | −0.0102 (18) | 0.0027 (18) |
C6 | 0.028 (2) | 0.032 (2) | 0.026 (2) | −0.0011 (18) | −0.0099 (18) | 0.0061 (17) |
C7 | 0.024 (2) | 0.036 (2) | 0.022 (2) | −0.0016 (19) | −0.0059 (17) | 0.0037 (18) |
C8 | 0.029 (2) | 0.036 (2) | 0.025 (2) | −0.0043 (19) | 0.0022 (17) | −0.0075 (18) |
C9 | 0.033 (2) | 0.046 (2) | 0.034 (2) | 0.002 (2) | −0.009 (2) | −0.007 (2) |
C10 | 0.037 (3) | 0.053 (3) | 0.039 (2) | 0.009 (2) | −0.003 (2) | −0.013 (2) |
C11 | 0.037 (3) | 0.050 (3) | 0.031 (2) | −0.002 (2) | −0.010 (2) | −0.009 (2) |
C12 | 0.029 (2) | 0.044 (2) | 0.031 (2) | −0.000 (2) | −0.0073 (19) | −0.0042 (19) |
C13 | 0.141 (7) | 0.273 (11) | 0.157 (7) | −0.066 (6) | −0.046 (5) | 0.155 (7) |
C14 | 0.122 (6) | 0.066 (4) | 0.087 (5) | 0.016 (4) | 0.006 (5) | −0.007 (4) |
C15 | 0.141 (7) | 0.273 (11) | 0.157 (7) | −0.066 (6) | −0.046 (5) | 0.155 (7) |
O1—C3 | 1.246 (5) | C8—C12 | 1.346 (6) |
O2—C4 | 1.226 (5) | C9—C10 | 1.381 (6) |
N1—C3 | 1.412 (5) | C9—H9 | 0.950 |
N1—C4 | 1.434 (5) | C10—H10 | 0.950 |
N1—C8 | 1.455 (5) | C11—C12 | 1.411 (6) |
N2—C10 | 1.297 (6) | C11—H11 | 0.950 |
N2—C11 | 1.320 (6) | C12—H12 | 0.950 |
C1—C1i | 1.424 (5) | C13—H13 | 0.950 |
C2—C1 | 1.474 (5) | C13—O3 | 1.216 (15) |
C2—C3 | 1.475 (5) | C13—N3 | 1.188 (14) |
C2—C7 | 1.365 (5) | C14—H14A | 0.980 |
C5—C1 | 1.395 (6) | C14—H14B | 0.980 |
C5—C4 | 1.474 (6) | C14—H14C | 0.980 |
C5—C6 | 1.436 (6) | C14—N3 | 1.394 (10) |
C6—H6 | 0.950 | C15—H15A | 0.980 |
C7—C6i | 1.405 (5) | C15—H15B | 0.980 |
C7—H7 | 0.950 | C15—H15C | 0.980 |
C8—C9 | 1.391 (6) | C15—N3 | 1.511 (14) |
C4···O3i | 2.802 (8) | H13···H15Cii | 1.981 |
C8—N1—C3 | 114.4 (3) | N1—C8—C12 | 118.2 (3) |
C8—N1—C4 | 119.0 (3) | C9—C8—C12 | 119.1 (4) |
C3—N1—C4 | 126.6 (3) | C8—C9—C10 | 119.5 (4) |
C10—N2—C11 | 115.4 (4) | C8—C9—H9 | 120.2 |
C13—N3—C14 | 130.2 (10) | C10—C9—H9 | 120.2 |
C13—N3—C15 | 117.8 (9) | N2—C10—C9 | 123.6 (4) |
C14—N3—C15 | 107.0 (7) | N2—C10—H10 | 118.2 |
C2—C1—C5 | 121.9 (3) | C9—C10—H10 | 118.2 |
C2—C1—C1i | 120.1 (3) | N2—C11—C12 | 127.0 (4) |
C5—C1—C1i | 117.9 (3) | N2—C11—H11 | 116.5 |
C7—C2—C1 | 120.6 (3) | C12—C11—H11 | 116.5 |
C7—C2—C3 | 118.1 (3) | C8—C12—C11 | 115.3 (4) |
C1—C2—C3 | 121.2 (3) | C8—C12—H12 | 122.3 |
O1—C3—N1 | 121.2 (3) | C11—C12—H12 | 122.3 |
O1—C3—C2 | 125.0 (3) | O3—C13—N3 | 140.3 (12) |
N1—C3—C2 | 113.9 (3) | H13—C13—O3 | 109.8 |
O2—C4—N1 | 120.7 (3) | H13—C13—N3 | 109.9 |
O2—C4—C5 | 121.0 (3) | H14A—C14—H14B | 109.5 |
N1—C4—C5 | 118.2 (3) | H14A—C14—H14C | 109.5 |
C1—C5—C4 | 118.2 (3) | H14A—C14—N3 | 109.5 |
C1—C5—C6 | 120.7 (3) | H14B—C14—H14C | 109.5 |
C4—C5—C6 | 121.1 (3) | H14B—C14—N3 | 109.5 |
C5—C6—C7i | 121.6 (3) | H14C—C14—N3 | 109.5 |
C5—C6—H6 | 119.2 | H15A—C15—H15B | 109.5 |
C7i—C6—H6 | 119.2 | H15A—C15—H15C | 109.5 |
C2—C7—H7 | 120.6 | H15A—C15—N3 | 109.5 |
C2—C7—C6i | 118.9 (3) | H15B—C15—H15C | 109.5 |
H7—C7—C6i | 120.6 | H15B—C15—N3 | 109.5 |
N1—C8—C9 | 122.7 (3) | H15C—C15—N3 | 109.5 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z. |