Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619003287/um5024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619003287/um5024polymorph1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619003287/um5024polymorph2sup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619003287/um5024sup4.pdf |
CCDC references: 1872270; 1872790; 1872791
Data collection: APEX II v.2013.6-2, (Bruker, 2013) for polymorph1. Cell refinement: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Data reduction: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Program(s) used to solve structure: SHELXT-2014/4 (Sheldrick, 2014) for polymorph1; SHELXS97 (Sheldrick, 1990) for polymorph2. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for polymorph1; SHELXL97 (Sheldrick, 1997) for polymorph2. Molecular graphics: Bruker SHELXTL (Bruker AXS Inc., 2013) for polymorph1.
C26H12N4O2 | Dx = 1.604 Mg m−3 |
Mr = 412.40 | Melting point: 744 K |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.41328 Å |
a = 13.1190 (8) Å | Cell parameters from 5223 reflections |
b = 4.7770 (3) Å | θ = 2.4–17.4° |
c = 27.3921 (17) Å | µ = 0.03 mm−1 |
β = 95.8533 (12)° | T = 100 K |
V = 1707.70 (18) Å3 | Plate, red |
Z = 4 | 0.05 × 0.02 × 0.01 mm |
F(000) = 848 |
Bruker APEX II CCD diffractometer | 3679 reflections with I > 2σ(I) |
Radiation source: Advanced photon source | Rint = 0.075 |
Diamond (111) monochromator | θmax = 17.7°, θmin = 0.9° |
φ–scan | h = −19→19 |
26791 measured reflections | k = −6→4 |
5376 independent reflections | l = −39→40 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.1151P)2 + 0.2566P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5376 reflections | Δρmax = 0.66 e Å−3 |
289 parameters | Δρmin = −0.32 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.54706 (10) | −0.1783 (3) | 0.45993 (5) | 0.0297 (3) | |
O2 | 0.56344 (10) | 0.8576 (3) | 0.27759 (5) | 0.0286 (3) | |
N1 | 0.70844 (11) | −0.0567 (3) | 0.49048 (5) | 0.0212 (3) | |
N2 | 0.86812 (11) | 0.0372 (3) | 0.52634 (5) | 0.0229 (3) | |
N3 | 0.72829 (11) | 0.9507 (3) | 0.30653 (5) | 0.0191 (3) | |
N4 | 0.89346 (11) | 1.0686 (3) | 0.32888 (5) | 0.0215 (3) | |
C1 | 0.62860 (13) | 0.1885 (3) | 0.41937 (6) | 0.0209 (3) | |
C2 | 0.71995 (13) | 0.3459 (3) | 0.41729 (6) | 0.0186 (3) | |
C3 | 0.80751 (13) | 0.2996 (3) | 0.45135 (6) | 0.0199 (3) | |
C4 | 0.89671 (14) | 0.4462 (4) | 0.44682 (6) | 0.0218 (3) | |
H4B | 0.9559 | 0.4093 | 0.4689 | 0.026* | |
C5 | 0.90112 (13) | 0.6486 (4) | 0.41013 (6) | 0.0218 (3) | |
H5A | 0.9628 | 0.7499 | 0.4079 | 0.026* | |
C6 | 0.81646 (13) | 0.7023 (3) | 0.37711 (6) | 0.0191 (3) | |
C7 | 0.72450 (13) | 0.5485 (3) | 0.38001 (6) | 0.0184 (3) | |
C8 | 0.63626 (13) | 0.5911 (4) | 0.34588 (6) | 0.0208 (3) | |
C9 | 0.54899 (13) | 0.4329 (4) | 0.34854 (7) | 0.0244 (4) | |
H9A | 0.4911 | 0.4610 | 0.3252 | 0.029* | |
C10 | 0.54526 (14) | 0.2317 (4) | 0.38528 (7) | 0.0242 (4) | |
H10A | 0.4849 | 0.1237 | 0.3868 | 0.029* | |
C11 | 0.62146 (13) | −0.0307 (4) | 0.45749 (6) | 0.0229 (4) | |
C12 | 0.72339 (14) | −0.2321 (4) | 0.53177 (6) | 0.0228 (4) | |
C13 | 0.66126 (15) | −0.4327 (4) | 0.55088 (7) | 0.0266 (4) | |
H13A | 0.5945 | −0.4743 | 0.5359 | 0.032* | |
C14 | 0.70286 (16) | −0.5680 (4) | 0.59313 (7) | 0.0288 (4) | |
H14A | 0.6638 | −0.7079 | 0.6074 | 0.035* | |
C15 | 0.80114 (16) | −0.5032 (4) | 0.61524 (7) | 0.0298 (4) | |
H15A | 0.8266 | −0.5993 | 0.6443 | 0.036* | |
C16 | 0.86218 (16) | −0.3031 (4) | 0.59594 (7) | 0.0269 (4) | |
H16A | 0.9286 | −0.2599 | 0.6112 | 0.032* | |
C17 | 0.82195 (14) | −0.1685 (4) | 0.55339 (6) | 0.0239 (4) | |
C18 | 0.79938 (13) | 0.0971 (4) | 0.49012 (6) | 0.0202 (3) | |
C19 | 0.63632 (13) | 0.8050 (3) | 0.30698 (6) | 0.0218 (3) | |
C20 | 0.75207 (13) | 1.1609 (3) | 0.27367 (6) | 0.0199 (3) | |
C21 | 0.69356 (14) | 1.2934 (4) | 0.23530 (6) | 0.0243 (4) | |
H21A | 0.6235 | 1.2484 | 0.2267 | 0.029* | |
C22 | 0.74393 (14) | 1.4964 (4) | 0.21025 (7) | 0.0247 (4) | |
H22A | 0.7077 | 1.5918 | 0.1834 | 0.030* | |
C23 | 0.84649 (14) | 1.5623 (4) | 0.22376 (6) | 0.0247 (4) | |
H23A | 0.8787 | 1.6999 | 0.2055 | 0.030* | |
C24 | 0.90276 (14) | 1.4335 (4) | 0.26291 (7) | 0.0247 (4) | |
H24A | 0.9721 | 1.4834 | 0.2722 | 0.030* | |
C25 | 0.85440 (13) | 1.2285 (4) | 0.28826 (6) | 0.0207 (3) | |
C26 | 0.81756 (12) | 0.9084 (3) | 0.33848 (6) | 0.0191 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0280 (7) | 0.0265 (7) | 0.0351 (8) | −0.0075 (5) | 0.0059 (6) | 0.0011 (5) |
O2 | 0.0232 (6) | 0.0261 (7) | 0.0345 (7) | −0.0015 (5) | −0.0070 (5) | 0.0039 (5) |
N1 | 0.0240 (7) | 0.0181 (7) | 0.0219 (7) | −0.0033 (5) | 0.0043 (5) | −0.0012 (5) |
N2 | 0.0287 (8) | 0.0203 (7) | 0.0197 (7) | −0.0003 (6) | 0.0022 (6) | 0.0000 (5) |
N3 | 0.0205 (7) | 0.0157 (7) | 0.0207 (7) | 0.0005 (5) | 0.0003 (5) | −0.0004 (5) |
N4 | 0.0233 (7) | 0.0189 (7) | 0.0224 (7) | −0.0009 (5) | 0.0027 (5) | −0.0003 (5) |
C1 | 0.0245 (8) | 0.0147 (8) | 0.0241 (8) | −0.0009 (6) | 0.0046 (6) | −0.0035 (6) |
C2 | 0.0234 (8) | 0.0138 (7) | 0.0188 (7) | 0.0008 (6) | 0.0026 (6) | −0.0023 (6) |
C3 | 0.0242 (8) | 0.0163 (8) | 0.0194 (7) | 0.0006 (6) | 0.0037 (6) | −0.0016 (6) |
C4 | 0.0254 (8) | 0.0201 (8) | 0.0194 (8) | −0.0002 (6) | 0.0000 (6) | −0.0007 (6) |
C5 | 0.0238 (8) | 0.0191 (8) | 0.0223 (8) | −0.0023 (6) | 0.0015 (6) | −0.0014 (6) |
C6 | 0.0228 (8) | 0.0150 (8) | 0.0197 (7) | 0.0012 (6) | 0.0030 (6) | −0.0029 (6) |
C7 | 0.0219 (8) | 0.0130 (7) | 0.0204 (7) | 0.0018 (6) | 0.0028 (6) | −0.0019 (5) |
C8 | 0.0245 (8) | 0.0152 (8) | 0.0225 (8) | 0.0017 (6) | 0.0019 (6) | −0.0018 (6) |
C9 | 0.0213 (8) | 0.0205 (9) | 0.0307 (9) | 0.0001 (6) | −0.0015 (7) | −0.0012 (7) |
C10 | 0.0230 (8) | 0.0196 (8) | 0.0301 (9) | −0.0006 (6) | 0.0026 (7) | −0.0022 (7) |
C11 | 0.0245 (8) | 0.0202 (8) | 0.0245 (8) | −0.0012 (6) | 0.0050 (7) | −0.0046 (6) |
C12 | 0.0319 (9) | 0.0170 (8) | 0.0204 (8) | 0.0023 (6) | 0.0073 (7) | −0.0012 (6) |
C13 | 0.0340 (10) | 0.0216 (9) | 0.0257 (9) | −0.0007 (7) | 0.0092 (7) | −0.0010 (7) |
C14 | 0.0411 (11) | 0.0213 (9) | 0.0256 (9) | −0.0013 (7) | 0.0122 (8) | 0.0009 (7) |
C15 | 0.0422 (11) | 0.0232 (9) | 0.0250 (9) | 0.0013 (8) | 0.0080 (8) | 0.0032 (7) |
C16 | 0.0362 (10) | 0.0227 (9) | 0.0224 (8) | 0.0013 (7) | 0.0059 (7) | 0.0010 (6) |
C17 | 0.0309 (9) | 0.0208 (8) | 0.0208 (8) | 0.0004 (7) | 0.0059 (7) | −0.0017 (6) |
C18 | 0.0240 (8) | 0.0173 (8) | 0.0193 (7) | −0.0007 (6) | 0.0024 (6) | −0.0026 (6) |
C19 | 0.0213 (8) | 0.0167 (8) | 0.0271 (9) | −0.0008 (6) | 0.0009 (6) | −0.0035 (6) |
C20 | 0.0246 (8) | 0.0161 (8) | 0.0191 (7) | 0.0012 (6) | 0.0024 (6) | −0.0020 (6) |
C21 | 0.0259 (8) | 0.0223 (9) | 0.0239 (8) | 0.0009 (6) | −0.0010 (6) | −0.0041 (6) |
C22 | 0.0314 (9) | 0.0195 (8) | 0.0230 (8) | 0.0007 (7) | 0.0018 (7) | −0.0011 (6) |
C23 | 0.0310 (9) | 0.0200 (9) | 0.0238 (8) | −0.0007 (7) | 0.0057 (7) | 0.0008 (6) |
C24 | 0.0265 (9) | 0.0208 (9) | 0.0272 (9) | −0.0009 (6) | 0.0047 (7) | 0.0003 (6) |
C25 | 0.0221 (8) | 0.0174 (8) | 0.0224 (8) | 0.0006 (6) | 0.0016 (6) | −0.0019 (6) |
C26 | 0.0204 (8) | 0.0160 (8) | 0.0206 (7) | 0.0011 (6) | 0.0006 (6) | −0.0023 (6) |
O1—C11 | 1.211 (2) | C8—C9 | 1.380 (2) |
O2—C19 | 1.212 (2) | C8—C19 | 1.476 (2) |
N1—C11 | 1.387 (2) | C9—C10 | 1.396 (3) |
N1—C18 | 1.402 (2) | C9—H9A | 0.9500 |
N1—C12 | 1.405 (2) | C10—H10A | 0.9500 |
N2—C18 | 1.303 (2) | C12—C13 | 1.394 (2) |
N2—C17 | 1.404 (2) | C12—C17 | 1.400 (3) |
N3—C19 | 1.394 (2) | C13—C14 | 1.388 (3) |
N3—C26 | 1.403 (2) | C13—H13A | 0.9500 |
N3—C20 | 1.405 (2) | C14—C15 | 1.402 (3) |
N4—C26 | 1.304 (2) | C14—H14A | 0.9500 |
N4—C25 | 1.403 (2) | C15—C16 | 1.386 (3) |
C1—C10 | 1.379 (2) | C15—H15A | 0.9500 |
C1—C2 | 1.421 (2) | C16—C17 | 1.387 (3) |
C1—C11 | 1.489 (2) | C16—H16A | 0.9500 |
C2—C7 | 1.413 (2) | C20—C21 | 1.389 (2) |
C2—C3 | 1.422 (2) | C20—C25 | 1.399 (2) |
C3—C4 | 1.380 (2) | C21—C22 | 1.393 (3) |
C3—C18 | 1.448 (2) | C21—H21A | 0.9500 |
C4—C5 | 1.400 (2) | C22—C23 | 1.395 (3) |
C4—H4B | 0.9500 | C22—H22A | 0.9500 |
C5—C6 | 1.383 (2) | C23—C24 | 1.383 (3) |
C5—H5A | 0.9500 | C23—H23A | 0.9500 |
C6—C7 | 1.422 (2) | C24—C25 | 1.391 (2) |
C6—C26 | 1.446 (2) | C24—H24A | 0.9500 |
C7—C8 | 1.426 (2) | ||
C11—N1—C18 | 126.34 (15) | C17—C12—N1 | 104.97 (15) |
C11—N1—C12 | 128.01 (15) | C14—C13—C12 | 115.98 (18) |
C18—N1—C12 | 105.62 (14) | C14—C13—H13A | 122.0 |
C18—N2—C17 | 104.68 (14) | C12—C13—H13A | 122.0 |
C19—N3—C26 | 126.20 (14) | C13—C14—C15 | 121.55 (18) |
C19—N3—C20 | 127.70 (14) | C13—C14—H14A | 119.2 |
C26—N3—C20 | 106.07 (13) | C15—C14—H14A | 119.2 |
C26—N4—C25 | 104.76 (14) | C16—C15—C14 | 121.97 (18) |
C10—C1—C2 | 120.49 (16) | C16—C15—H15A | 119.0 |
C10—C1—C11 | 118.55 (15) | C14—C15—H15A | 119.0 |
C2—C1—C11 | 120.94 (16) | C15—C16—C17 | 117.05 (18) |
C7—C2—C1 | 119.31 (15) | C15—C16—H16A | 121.5 |
C7—C2—C3 | 119.36 (15) | C17—C16—H16A | 121.5 |
C1—C2—C3 | 121.31 (15) | C16—C17—C12 | 120.72 (17) |
C4—C3—C2 | 119.85 (15) | C16—C17—N2 | 128.30 (17) |
C4—C3—C18 | 122.10 (15) | C12—C17—N2 | 110.98 (15) |
C2—C3—C18 | 118.05 (15) | N2—C18—N1 | 113.75 (15) |
C3—C4—C5 | 120.83 (16) | N2—C18—C3 | 127.46 (16) |
C3—C4—H4B | 119.6 | N1—C18—C3 | 118.78 (15) |
C5—C4—H4B | 119.6 | O2—C19—N3 | 121.03 (16) |
C6—C5—C4 | 120.56 (16) | O2—C19—C8 | 124.37 (16) |
C6—C5—H5A | 119.7 | N3—C19—C8 | 114.59 (14) |
C4—C5—H5A | 119.7 | C21—C20—C25 | 123.44 (16) |
C5—C6—C7 | 119.81 (15) | C21—C20—N3 | 131.97 (16) |
C5—C6—C26 | 122.51 (15) | C25—C20—N3 | 104.56 (14) |
C7—C6—C26 | 117.68 (15) | C20—C21—C22 | 115.89 (17) |
C2—C7—C6 | 119.54 (15) | C20—C21—H21A | 122.1 |
C2—C7—C8 | 118.71 (15) | C22—C21—H21A | 122.1 |
C6—C7—C8 | 121.75 (15) | C21—C22—C23 | 121.32 (17) |
C9—C8—C7 | 120.62 (16) | C21—C22—H22A | 119.3 |
C9—C8—C19 | 118.60 (15) | C23—C22—H22A | 119.3 |
C7—C8—C19 | 120.78 (15) | C24—C23—C22 | 121.98 (17) |
C8—C9—C10 | 120.36 (16) | C24—C23—H23A | 119.0 |
C8—C9—H9A | 119.8 | C22—C23—H23A | 119.0 |
C10—C9—H9A | 119.8 | C23—C24—C25 | 117.77 (17) |
C1—C10—C9 | 120.49 (16) | C23—C24—H24A | 121.1 |
C1—C10—H10A | 119.8 | C25—C24—H24A | 121.1 |
C9—C10—H10A | 119.8 | C24—C25—C20 | 119.57 (16) |
O1—C11—N1 | 121.73 (17) | C24—C25—N4 | 129.14 (16) |
O1—C11—C1 | 123.84 (17) | C20—C25—N4 | 111.30 (15) |
N1—C11—C1 | 114.43 (15) | N4—C26—N3 | 113.31 (15) |
C13—C12—C17 | 122.72 (17) | N4—C26—C6 | 127.72 (15) |
C13—C12—N1 | 132.31 (17) | N3—C26—C6 | 118.96 (15) |
C10—C1—C2—C7 | 0.3 (2) | N1—C12—C17—C16 | 179.41 (16) |
C11—C1—C2—C7 | 178.79 (14) | C13—C12—C17—N2 | 179.05 (15) |
C10—C1—C2—C3 | −178.41 (16) | N1—C12—C17—N2 | −0.76 (19) |
C11—C1—C2—C3 | 0.1 (2) | C18—N2—C17—C16 | −179.52 (18) |
C7—C2—C3—C4 | −1.9 (2) | C18—N2—C17—C12 | 0.67 (19) |
C1—C2—C3—C4 | 176.75 (15) | C17—N2—C18—N1 | −0.31 (19) |
C7—C2—C3—C18 | 178.01 (14) | C17—N2—C18—C3 | 179.41 (16) |
C1—C2—C3—C18 | −3.3 (2) | C11—N1—C18—N2 | 177.90 (16) |
C2—C3—C4—C5 | 2.5 (3) | C12—N1—C18—N2 | −0.14 (19) |
C18—C3—C4—C5 | −177.47 (15) | C11—N1—C18—C3 | −1.9 (2) |
C3—C4—C5—C6 | −1.1 (3) | C12—N1—C18—C3 | −179.89 (14) |
C4—C5—C6—C7 | −0.8 (2) | C4—C3—C18—N2 | 4.4 (3) |
C4—C5—C6—C26 | −179.71 (15) | C2—C3—C18—N2 | −175.56 (16) |
C1—C2—C7—C6 | −178.63 (14) | C4—C3—C18—N1 | −175.92 (15) |
C3—C2—C7—C6 | 0.1 (2) | C2—C3—C18—N1 | 4.1 (2) |
C1—C2—C7—C8 | 0.8 (2) | C26—N3—C19—O2 | −179.87 (16) |
C3—C2—C7—C8 | 179.53 (14) | C20—N3—C19—O2 | −2.1 (3) |
C5—C6—C7—C2 | 1.3 (2) | C26—N3—C19—C8 | 0.9 (2) |
C26—C6—C7—C2 | −179.75 (14) | C20—N3—C19—C8 | 178.74 (15) |
C5—C6—C7—C8 | −178.17 (15) | C9—C8—C19—O2 | 2.0 (3) |
C26—C6—C7—C8 | 0.8 (2) | C7—C8—C19—O2 | −178.00 (16) |
C2—C7—C8—C9 | −1.5 (2) | C9—C8—C19—N3 | −178.80 (15) |
C6—C7—C8—C9 | 177.92 (15) | C7—C8—C19—N3 | 1.2 (2) |
C2—C7—C8—C19 | 178.52 (14) | C19—N3—C20—C21 | 4.0 (3) |
C6—C7—C8—C19 | −2.0 (2) | C26—N3—C20—C21 | −177.86 (17) |
C7—C8—C9—C10 | 1.1 (3) | C19—N3—C20—C25 | −177.90 (15) |
C19—C8—C9—C10 | −178.94 (16) | C26—N3—C20—C25 | 0.25 (17) |
C2—C1—C10—C9 | −0.7 (3) | C25—C20—C21—C22 | 2.1 (3) |
C11—C1—C10—C9 | −179.27 (15) | N3—C20—C21—C22 | 179.92 (16) |
C8—C9—C10—C1 | 0.0 (3) | C20—C21—C22—C23 | −0.8 (3) |
C18—N1—C11—O1 | 178.06 (16) | C21—C22—C23—C24 | −1.0 (3) |
C12—N1—C11—O1 | −4.3 (3) | C22—C23—C24—C25 | 1.4 (3) |
C18—N1—C11—C1 | −1.3 (2) | C23—C24—C25—C20 | −0.2 (3) |
C12—N1—C11—C1 | 176.29 (15) | C23—C24—C25—N4 | −179.75 (17) |
C10—C1—C11—O1 | 1.4 (3) | C21—C20—C25—C24 | −1.7 (3) |
C2—C1—C11—O1 | −177.17 (16) | N3—C20—C25—C24 | −179.97 (15) |
C10—C1—C11—N1 | −179.26 (15) | C21—C20—C25—N4 | 177.99 (15) |
C2—C1—C11—N1 | 2.2 (2) | N3—C20—C25—N4 | −0.34 (18) |
C11—N1—C12—C13 | 2.8 (3) | C26—N4—C25—C24 | 179.87 (17) |
C18—N1—C12—C13 | −179.25 (18) | C26—N4—C25—C20 | 0.28 (18) |
C11—N1—C12—C17 | −177.46 (16) | C25—N4—C26—N3 | −0.11 (18) |
C18—N1—C12—C17 | 0.53 (17) | C25—N4—C26—C6 | −179.84 (16) |
C17—C12—C13—C14 | 0.0 (3) | C19—N3—C26—N4 | 178.09 (15) |
N1—C12—C13—C14 | 179.79 (17) | C20—N3—C26—N4 | −0.10 (19) |
C12—C13—C14—C15 | 0.6 (3) | C19—N3—C26—C6 | −2.1 (2) |
C13—C14—C15—C16 | −0.6 (3) | C20—N3—C26—C6 | 179.66 (14) |
C14—C15—C16—C17 | −0.2 (3) | C5—C6—C26—N4 | −0.1 (3) |
C15—C16—C17—C12 | 0.8 (3) | C7—C6—C26—N4 | −179.10 (16) |
C15—C16—C17—N2 | −178.99 (17) | C5—C6—C26—N3 | −179.86 (15) |
C13—C12—C17—C16 | −0.8 (3) | C7—C6—C26—N3 | 1.2 (2) |
C26H12N4O2 | Dx = 1.559 Mg m−3 |
Mr = 412.40 | Melting point: 741 K |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 16.971 (2) Å | Cell parameters from 1796 reflections |
b = 7.3707 (9) Å | θ = 2.6–72.3° |
c = 14.0809 (17) Å | µ = 0.83 mm−1 |
β = 94.09 (1)° | T = 130 K |
V = 1756.8 (4) Å3 | Plate, dark red |
Z = 4 | 0.14 × 0.08 × 0.01 mm |
F(000) = 848 |
BRUKER AXS (Kappa APEX II Duo) diffractometer | 1498 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.0000 |
Graphite monochromator | θmax = 50.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38 | h = −16→16 |
Tmin = 0.890, Tmax = 0.989 | k = −7→7 |
1794 measured reflections | l = −13→13 |
1794 independent reflections |
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)] = 0.110 | H-atom parameters constrained |
wR(F2) = 0.321 | w = 1/[σ2(Fo2) + (0.1921P)2 + 7.3569P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.055 |
1794 reflections | Δρmax = 0.74 e Å−3 |
290 parameters | Δρmin = −0.53 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (12) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.9318 (4) | 0.1829 (9) | 0.9837 (6) | 0.025 (2) | |
N3 | 0.5571 (4) | −0.1941 (10) | 0.9621 (6) | 0.030 (2) | |
C2 | 0.7827 (5) | 0.0397 (11) | 0.9767 (8) | 0.027 (2) | |
C1 | 0.8203 (5) | 0.0628 (12) | 0.8906 (7) | 0.027 (2) | |
C7 | 0.7053 (5) | −0.0487 (12) | 0.9727 (7) | 0.026 (2) | |
C3 | 0.8185 (5) | 0.0904 (12) | 1.0668 (7) | 0.029 (3) | |
O1 | 0.9374 (4) | 0.1650 (9) | 0.8231 (6) | 0.043 (2) | |
C6 | 0.6687 (5) | −0.0713 (11) | 1.0593 (6) | 0.023 (2) | |
N4 | 0.5446 (4) | −0.1890 (10) | 1.1219 (7) | 0.030 (2) | |
O2 | 0.5527 (4) | −0.2316 (10) | 0.8032 (6) | 0.044 (2) | |
C19 | 0.5917 (6) | −0.1767 (12) | 0.8761 (8) | 0.029 (3) | |
C26 | 0.5925 (5) | −0.1514 (12) | 1.0495 (8) | 0.025 (2) | |
C8 | 0.6699 (5) | −0.0953 (11) | 0.8841 (7) | 0.026 (2) | |
N2 | 0.9422 (4) | 0.2268 (10) | 1.1407 (5) | 0.025 (2) | |
C5 | 0.7076 (5) | −0.0181 (12) | 1.1476 (7) | 0.031 (3) | |
H5 | 0.6828 | −0.0405 | 1.2048 | 0.037* | |
C11 | 0.8975 (6) | 0.1380 (12) | 0.8933 (9) | 0.035 (3) | |
C18 | 0.8944 (5) | 0.1663 (11) | 1.0670 (7) | 0.027 (3) | |
C9 | 0.7082 (6) | −0.0681 (14) | 0.8010 (7) | 0.035 (3) | |
H9 | 0.6826 | −0.1026 | 0.7415 | 0.043* | |
C10 | 0.7810 (6) | 0.0066 (13) | 0.8035 (8) | 0.038 (3) | |
H10 | 0.8062 | 0.0217 | 0.7459 | 0.046* | |
C4 | 0.7793 (5) | 0.0640 (12) | 1.1520 (7) | 0.029 (3) | |
H4 | 0.8033 | 0.1037 | 1.2115 | 0.034* | |
C20 | 0.4830 (5) | −0.2732 (12) | 0.9790 (8) | 0.027 (3) | |
C22 | 0.3572 (6) | −0.4096 (12) | 0.9563 (9) | 0.036 (3) | |
H22 | 0.3151 | −0.4580 | 0.9159 | 0.044* | |
C14 | 1.1353 (5) | 0.3798 (13) | 0.9991 (8) | 0.033 (3) | |
H14 | 1.1798 | 0.4100 | 0.9649 | 0.040* | |
C15 | 1.1406 (6) | 0.4083 (13) | 1.0947 (8) | 0.036 (3) | |
H15 | 1.1878 | 0.4583 | 1.1241 | 0.043* | |
C21 | 0.4237 (6) | −0.3440 (12) | 0.9149 (8) | 0.034 (3) | |
H21 | 0.4286 | −0.3470 | 0.8481 | 0.041* | |
C23 | 0.3498 (6) | −0.4076 (13) | 1.0502 (8) | 0.034 (3) | |
H23 | 0.3032 | −0.4555 | 1.0741 | 0.041* | |
C17 | 1.0135 (6) | 0.2878 (12) | 1.1027 (8) | 0.036 (3) | |
C12 | 1.0069 (5) | 0.2655 (11) | 1.0051 (7) | 0.018 (2) | |
C25 | 0.4751 (6) | −0.2689 (13) | 1.0758 (7) | 0.028 (3) | |
C13 | 1.0685 (6) | 0.3088 (13) | 0.9477 (8) | 0.038 (3) | |
H13 | 1.0652 | 0.2917 | 0.8807 | 0.045* | |
C16 | 1.0794 (6) | 0.3666 (13) | 1.1503 (8) | 0.039 (3) | |
H16 | 1.0821 | 0.3901 | 1.2167 | 0.047* | |
C24 | 0.4092 (5) | −0.3364 (12) | 1.1147 (8) | 0.034 (3) | |
H24 | 0.4040 | −0.3351 | 1.1814 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.022 (4) | 0.014 (4) | 0.041 (6) | 0.003 (3) | 0.006 (4) | 0.002 (4) |
N3 | 0.027 (5) | 0.033 (5) | 0.029 (6) | −0.005 (4) | −0.011 (5) | −0.006 (4) |
C2 | 0.023 (5) | 0.018 (5) | 0.041 (7) | −0.006 (4) | 0.005 (5) | −0.001 (5) |
C1 | 0.019 (5) | 0.023 (5) | 0.038 (7) | 0.003 (4) | 0.002 (5) | 0.015 (5) |
C7 | 0.024 (5) | 0.022 (5) | 0.034 (7) | 0.003 (4) | 0.000 (5) | −0.010 (5) |
C3 | 0.016 (5) | 0.032 (6) | 0.039 (7) | 0.009 (4) | 0.012 (5) | 0.005 (5) |
O1 | 0.029 (4) | 0.052 (5) | 0.048 (5) | −0.003 (3) | 0.012 (4) | 0.009 (4) |
C6 | 0.027 (6) | 0.020 (5) | 0.021 (6) | 0.004 (4) | 0.004 (5) | −0.004 (5) |
N4 | 0.017 (4) | 0.026 (5) | 0.048 (6) | 0.001 (3) | 0.012 (4) | −0.002 (4) |
O2 | 0.040 (4) | 0.049 (5) | 0.042 (5) | −0.013 (4) | −0.006 (4) | −0.015 (4) |
C19 | 0.040 (6) | 0.017 (5) | 0.030 (7) | 0.006 (4) | 0.012 (6) | 0.010 (5) |
C26 | 0.011 (5) | 0.021 (5) | 0.046 (7) | 0.008 (4) | 0.011 (5) | 0.010 (5) |
C8 | 0.021 (5) | 0.021 (5) | 0.036 (7) | −0.009 (4) | 0.002 (5) | −0.001 (5) |
N2 | 0.024 (4) | 0.024 (4) | 0.025 (5) | 0.001 (4) | −0.005 (4) | −0.004 (4) |
C5 | 0.031 (6) | 0.028 (6) | 0.034 (7) | 0.005 (5) | 0.007 (5) | 0.010 (5) |
C11 | 0.025 (6) | 0.028 (6) | 0.051 (8) | −0.002 (5) | 0.010 (6) | 0.002 (5) |
C18 | 0.030 (6) | 0.018 (5) | 0.031 (7) | 0.006 (4) | 0.002 (6) | 0.002 (5) |
C9 | 0.034 (6) | 0.047 (7) | 0.025 (7) | −0.001 (5) | −0.003 (5) | −0.004 (5) |
C10 | 0.039 (7) | 0.043 (7) | 0.035 (7) | 0.000 (5) | 0.011 (5) | −0.003 (6) |
C4 | 0.016 (5) | 0.034 (6) | 0.036 (7) | −0.003 (4) | 0.001 (5) | −0.011 (5) |
C20 | 0.011 (5) | 0.020 (5) | 0.051 (9) | −0.013 (4) | 0.001 (5) | 0.001 (5) |
C22 | 0.026 (6) | 0.018 (5) | 0.067 (9) | 0.000 (4) | 0.016 (6) | 0.007 (6) |
C14 | 0.014 (5) | 0.031 (6) | 0.054 (8) | −0.001 (4) | 0.008 (5) | −0.002 (5) |
C15 | 0.025 (6) | 0.041 (6) | 0.041 (8) | 0.000 (5) | −0.007 (5) | −0.006 (6) |
C21 | 0.034 (6) | 0.027 (6) | 0.043 (7) | 0.010 (5) | 0.005 (5) | 0.008 (5) |
C23 | 0.018 (5) | 0.033 (6) | 0.052 (8) | 0.003 (5) | 0.013 (5) | 0.008 (5) |
C17 | 0.031 (6) | 0.025 (6) | 0.051 (9) | 0.000 (5) | 0.000 (6) | 0.014 (5) |
C12 | 0.017 (5) | 0.021 (5) | 0.017 (6) | −0.015 (4) | 0.004 (4) | −0.002 (4) |
C25 | 0.033 (7) | 0.029 (6) | 0.021 (7) | 0.016 (5) | 0.007 (5) | 0.001 (5) |
C13 | 0.043 (7) | 0.027 (6) | 0.044 (7) | 0.006 (5) | 0.005 (6) | −0.001 (5) |
C16 | 0.031 (6) | 0.039 (6) | 0.048 (7) | −0.003 (5) | 0.010 (6) | −0.008 (5) |
C24 | 0.021 (6) | 0.035 (6) | 0.044 (7) | 0.000 (4) | 0.002 (6) | −0.002 (5) |
N1—C18 | 1.378 (13) | C5—H5 | 0.9500 |
N1—C11 | 1.401 (13) | C9—C10 | 1.351 (14) |
N1—C12 | 1.425 (11) | C9—H9 | 0.9500 |
N3—C26 | 1.368 (13) | C10—H10 | 0.9500 |
N3—C19 | 1.389 (14) | C4—H4 | 0.9500 |
N3—C20 | 1.421 (12) | C20—C25 | 1.379 (14) |
C2—C1 | 1.419 (14) | C20—C21 | 1.405 (14) |
C2—C3 | 1.417 (15) | C22—C23 | 1.336 (16) |
C2—C7 | 1.464 (13) | C22—C21 | 1.394 (14) |
C1—C10 | 1.417 (15) | C22—H22 | 0.9500 |
C1—C11 | 1.420 (13) | C14—C15 | 1.359 (15) |
C7—C8 | 1.389 (14) | C14—C13 | 1.403 (14) |
C7—C6 | 1.417 (14) | C14—H14 | 0.9500 |
C3—C18 | 1.405 (13) | C15—C16 | 1.379 (14) |
C3—C4 | 1.426 (14) | C15—H15 | 0.9500 |
O1—C11 | 1.254 (13) | C21—H21 | 0.9500 |
C6—C26 | 1.420 (13) | C23—C24 | 1.410 (15) |
C6—C5 | 1.420 (14) | C23—H23 | 0.9500 |
N4—C26 | 1.376 (13) | C17—C12 | 1.380 (15) |
N4—C25 | 1.432 (12) | C17—C16 | 1.389 (14) |
O2—C19 | 1.249 (13) | C12—C13 | 1.403 (13) |
C19—C8 | 1.453 (14) | C25—C24 | 1.372 (14) |
C8—C9 | 1.393 (15) | C13—H13 | 0.9500 |
N2—C18 | 1.347 (12) | C16—H16 | 0.9500 |
N2—C17 | 1.430 (13) | C24—H24 | 0.9500 |
C5—C4 | 1.357 (13) | ||
C18—N1—C11 | 124.4 (8) | C8—C9—H9 | 119.4 |
C18—N1—C12 | 108.5 (8) | C9—C10—C1 | 121.0 (10) |
C11—N1—C12 | 126.9 (8) | C9—C10—H10 | 119.5 |
C26—N3—C19 | 125.3 (8) | C1—C10—H10 | 119.5 |
C26—N3—C20 | 106.3 (8) | C5—C4—C3 | 119.5 (9) |
C19—N3—C20 | 128.2 (8) | C5—C4—H4 | 120.3 |
C1—C2—C3 | 122.9 (8) | C3—C4—H4 | 120.3 |
C1—C2—C7 | 118.6 (9) | C25—C20—C21 | 121.8 (9) |
C3—C2—C7 | 118.5 (9) | C25—C20—N3 | 107.9 (8) |
C2—C1—C10 | 119.4 (8) | C21—C20—N3 | 130.3 (10) |
C2—C1—C11 | 119.6 (10) | C23—C22—C21 | 123.1 (11) |
C10—C1—C11 | 120.9 (10) | C23—C22—H22 | 118.5 |
C8—C7—C6 | 123.7 (8) | C21—C22—H22 | 118.5 |
C8—C7—C2 | 118.3 (9) | C15—C14—C13 | 124.2 (10) |
C6—C7—C2 | 117.8 (9) | C15—C14—H14 | 117.9 |
C18—C3—C2 | 116.2 (9) | C13—C14—H14 | 117.9 |
C18—C3—C4 | 122.3 (9) | C14—C15—C16 | 121.9 (9) |
C2—C3—C4 | 121.5 (8) | C14—C15—H15 | 119.1 |
C7—C6—C26 | 114.7 (9) | C16—C15—H15 | 119.0 |
C7—C6—C5 | 121.1 (8) | C22—C21—C20 | 115.1 (10) |
C26—C6—C5 | 124.2 (9) | C22—C21—H21 | 122.4 |
C26—N4—C25 | 105.0 (8) | C20—C21—H21 | 122.4 |
O2—C19—N3 | 117.0 (8) | C22—C23—C24 | 121.9 (10) |
O2—C19—C8 | 128.7 (9) | C22—C23—H23 | 119.0 |
N3—C19—C8 | 114.3 (9) | C24—C23—H23 | 119.1 |
N3—C26—N4 | 112.0 (8) | C12—C17—C16 | 122.4 (9) |
N3—C26—C6 | 121.4 (9) | C12—C17—N2 | 108.9 (8) |
N4—C26—C6 | 126.5 (10) | C16—C17—N2 | 128.6 (10) |
C7—C8—C9 | 121.4 (8) | C17—C12—C13 | 122.4 (9) |
C7—C8—C19 | 120.5 (9) | C17—C12—N1 | 105.6 (8) |
C9—C8—C19 | 118.2 (9) | C13—C12—N1 | 131.8 (9) |
C18—N2—C17 | 107.1 (8) | C24—C25—C20 | 121.8 (10) |
C4—C5—C6 | 121.5 (9) | C24—C25—N4 | 129.4 (9) |
C4—C5—H5 | 119.2 | C20—C25—N4 | 108.8 (8) |
C6—C5—H5 | 119.3 | C14—C13—C12 | 113.3 (10) |
O1—C11—N1 | 117.8 (8) | C14—C13—H13 | 123.3 |
O1—C11—C1 | 126.2 (11) | C12—C13—H13 | 123.3 |
N1—C11—C1 | 116.0 (10) | C15—C16—C17 | 115.6 (10) |
N2—C18—N1 | 109.7 (8) | C15—C16—H16 | 122.2 |
N2—C18—C3 | 129.4 (9) | C17—C16—H16 | 122.2 |
N1—C18—C3 | 120.8 (9) | C25—C24—C23 | 116.3 (10) |
C10—C9—C8 | 121.2 (10) | C25—C24—H24 | 121.9 |
C10—C9—H9 | 119.4 | C23—C24—H24 | 121.8 |
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