Metal–organic frameworks (MOFs) have attracted much interest in the fields of gas separation and storage, catalysis synthesis, nonlinear optics, sensors, luminescence, magnetism, photocatalysis gradation and crystal engineering because of their diverse properties and intriguing topologies. A Cu–MOF, namely poly[[(μ2-succinato-κ2O:O′){μ2-tris[4-(1,2,4-triazol-1-yl)phenyl]amine-κ2N:N′}copper(II)] dihydrate], {[Cu(C4H4O4)(C24H18N10)]·2H2O}n or {[Cu(suc)(ttpa)]·2H2O}n, (I), was synthesized by the hydrothermal method using tris[4-(1,2,4-triazol-1-yl)phenyl]amine (ttpa) and succinate (suc2−), and characterized by IR, powder X-ray diffraction (PXRD), luminescence, optical band gap and valence band X-ray photoelectron spectroscopy (VB XPS). Cu–MOF (I) shows a twofold interpenetrating 4-coordinated three-dimensional CdSO4 topology with point symbol {65·8}. It presents good photocatalytic degradation of methylene blue (MB) and rhodamine B (RhB) under visible-light irradiation. A photocatalytic mechanism was proposed and confirmed.
Supporting information
CCDC reference: 1937130
Data collection: APEX3 (Bruker, 2010); cell refinement: APEX3 (Bruker, 2010); data reduction: APEX3 (Bruker, 2010); program(s) used to solve structure: SHELXL2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009; Bourhis et al.,
2015).
Poly[[(µ
2-succinato-
κ2O:
O'){µ
2-tris[4-(1,2,4-triazol-1-yl)phenyl]amine-
κ2N:
N'}copper(II)] dihydrate]
top
Crystal data top
[Cu(C4H4O4)(C24H18N10)]·2H2O | F(000) = 1364 |
Mr = 662.13 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2402 (4) Å | Cell parameters from 9748 reflections |
b = 25.5312 (11) Å | θ = 2.3–27.5° |
c = 12.5727 (6) Å | µ = 0.82 mm−1 |
β = 103.173 (2)° | T = 150 K |
V = 2888.0 (2) Å3 | Block, blue |
Z = 4 | 0.50 × 0.40 × 0.10 mm |
Data collection top
Bruker D8 Quest diffractometer | 5455 reflections with I > 2σ(I) |
ω scans | Rint = 0.045 |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | θmax = 27.6°, θmin = 2.3° |
Tmin = 0.624, Tmax = 0.746 | h = −12→12 |
77240 measured reflections | k = −33→33 |
6658 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0427P)2 + 2.1642P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.46 e Å−3 |
6658 reflections | Δρmin = −0.56 e Å−3 |
422 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.0076 (6) |
Primary atom site location: iterative | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 1.000000 | 0.500000 | 1.000000 | 0.01882 (9) | |
Cu2 | 0.500000 | 0.500000 | 0.500000 | 0.02253 (10) | |
O1 | 0.94300 (16) | 0.55864 (6) | 0.82264 (12) | 0.0329 (3) | |
O2 | 1.05308 (14) | 0.48187 (5) | 0.86144 (10) | 0.0233 (3) | |
O3 | 0.77361 (17) | 0.47416 (6) | 0.61660 (13) | 0.0369 (4) | |
O4 | 0.68498 (16) | 0.53794 (6) | 0.50076 (11) | 0.0314 (3) | |
N1 | 0.80187 (16) | 0.46784 (6) | 0.95003 (13) | 0.0227 (3) | |
N2 | 0.55976 (18) | 0.44959 (7) | 0.92691 (13) | 0.0283 (4) | |
N3 | 0.61958 (16) | 0.42306 (6) | 0.85378 (12) | 0.0211 (3) | |
N4 | 0.02373 (18) | 0.04497 (6) | 0.87395 (13) | 0.0250 (3) | |
N5 | −0.0361 (2) | 0.07619 (7) | 0.70229 (13) | 0.0333 (4) | |
N6 | 0.08336 (16) | 0.10147 (6) | 0.76264 (12) | 0.0210 (3) | |
N7 | 0.1527 (2) | 0.32683 (8) | −0.05164 (14) | 0.0364 (4) | |
N8 | 0.2526 (2) | 0.25752 (7) | 0.04845 (14) | 0.0340 (4) | |
N9 | 0.22165 (18) | 0.29617 (6) | 0.11356 (13) | 0.0254 (3) | |
N10 | 0.32142 (18) | 0.26984 (6) | 0.56828 (12) | 0.0228 (3) | |
C1 | 0.7630 (2) | 0.43412 (7) | 0.86818 (15) | 0.0237 (4) | |
H1 | 0.827619 | 0.420120 | 0.826475 | 0.028* | |
C2 | 0.6738 (2) | 0.47598 (8) | 0.98344 (16) | 0.0285 (4) | |
H2 | 0.667274 | 0.498619 | 1.042136 | 0.034* | |
C3 | 0.5874 (2) | 0.37418 (7) | 0.68510 (15) | 0.0218 (4) | |
H3 | 0.671340 | 0.391581 | 0.670035 | 0.026* | |
C4 | 0.53506 (19) | 0.38740 (7) | 0.77629 (14) | 0.0199 (4) | |
C5 | 0.4062 (2) | 0.36572 (8) | 0.79523 (15) | 0.0256 (4) | |
H5 | 0.368831 | 0.376403 | 0.856238 | 0.031* | |
C6 | 0.3326 (2) | 0.32814 (8) | 0.72353 (15) | 0.0249 (4) | |
H6 | 0.241900 | 0.313841 | 0.733821 | 0.030* | |
C7 | 0.39018 (19) | 0.31115 (7) | 0.63683 (14) | 0.0197 (4) | |
C8 | 0.5160 (2) | 0.33544 (7) | 0.61643 (14) | 0.0218 (4) | |
H8 | 0.552798 | 0.325270 | 0.554859 | 0.026* | |
C9 | 0.1629 (2) | 0.33709 (8) | 0.05288 (16) | 0.0302 (4) | |
H9 | 0.132935 | 0.368894 | 0.080659 | 0.036* | |
C10 | 0.2087 (3) | 0.27795 (9) | −0.04914 (17) | 0.0374 (5) | |
H10 | 0.215781 | 0.259648 | −0.113551 | 0.045* | |
C11 | 0.2511 (2) | 0.28968 (8) | 0.22965 (14) | 0.0223 (4) | |
C12 | 0.2359 (2) | 0.33199 (7) | 0.29534 (15) | 0.0276 (4) | |
H12 | 0.210260 | 0.365512 | 0.263897 | 0.033* | |
C13 | 0.2585 (2) | 0.32502 (7) | 0.40717 (15) | 0.0270 (4) | |
H13 | 0.248089 | 0.353921 | 0.452431 | 0.032* | |
C14 | 0.29633 (19) | 0.27606 (7) | 0.45372 (14) | 0.0201 (4) | |
C15 | 0.3128 (2) | 0.23421 (7) | 0.38691 (15) | 0.0241 (4) | |
H15 | 0.339835 | 0.200743 | 0.418211 | 0.029* | |
C16 | 0.2901 (2) | 0.24087 (7) | 0.27517 (16) | 0.0253 (4) | |
H16 | 0.301210 | 0.212073 | 0.229845 | 0.030* | |
C17 | 0.1181 (2) | 0.08306 (7) | 0.86503 (15) | 0.0229 (4) | |
H17 | 0.197158 | 0.095229 | 0.921847 | 0.027* | |
C18 | −0.0689 (2) | 0.04272 (8) | 0.77293 (16) | 0.0329 (5) | |
H18 | −0.150161 | 0.019047 | 0.754972 | 0.039* | |
C19 | 0.1499 (2) | 0.14315 (7) | 0.71261 (14) | 0.0201 (4) | |
C20 | 0.0752 (2) | 0.16070 (8) | 0.61071 (15) | 0.0257 (4) | |
H20 | −0.014733 | 0.144343 | 0.574170 | 0.031* | |
C21 | 0.1322 (2) | 0.20221 (8) | 0.56217 (15) | 0.0260 (4) | |
H21 | 0.080528 | 0.214518 | 0.492550 | 0.031* | |
C22 | 0.2651 (2) | 0.22605 (7) | 0.61488 (14) | 0.0202 (4) | |
C23 | 0.3412 (2) | 0.20623 (7) | 0.71536 (15) | 0.0223 (4) | |
H23 | 0.434111 | 0.221106 | 0.750412 | 0.027* | |
C24 | 0.2837 (2) | 0.16509 (7) | 0.76517 (14) | 0.0228 (4) | |
H24 | 0.335547 | 0.152250 | 0.834293 | 0.027* | |
C25 | 1.0103 (2) | 0.52075 (8) | 0.79691 (15) | 0.0237 (4) | |
C26 | 1.0526 (2) | 0.51815 (9) | 0.68682 (17) | 0.0312 (4) | |
H26A | 1.149912 | 0.535577 | 0.693090 | 0.037* | |
H26B | 1.064073 | 0.480986 | 0.667846 | 0.037* | |
C27 | 0.9389 (2) | 0.54387 (8) | 0.59512 (16) | 0.0285 (4) | |
H27A | 0.923496 | 0.580522 | 0.615729 | 0.034* | |
H27B | 0.978720 | 0.544676 | 0.528404 | 0.034* | |
C28 | 0.7900 (2) | 0.51567 (8) | 0.56976 (16) | 0.0264 (4) | |
O5 | 1.00355 (18) | 0.38122 (6) | 0.75601 (13) | 0.0341 (3) | |
H5A | 1.030 (3) | 0.4118 (7) | 0.772 (2) | 0.041* | |
H5B | 1.048 (3) | 0.3629 (9) | 0.8094 (17) | 0.041* | |
O6 | 0.8782 (2) | 0.35081 (8) | 0.53560 (14) | 0.0523 (5) | |
H6A | 0.929 (3) | 0.3617 (12) | 0.5931 (18) | 0.063* | |
H6B | 0.866 (3) | 0.3192 (7) | 0.545 (3) | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01654 (15) | 0.01973 (16) | 0.01887 (16) | −0.00192 (11) | 0.00132 (11) | −0.00571 (12) |
Cu2 | 0.02773 (18) | 0.02095 (17) | 0.02073 (17) | 0.00054 (13) | 0.00932 (13) | −0.00630 (12) |
O1 | 0.0401 (8) | 0.0282 (7) | 0.0312 (8) | 0.0049 (6) | 0.0098 (6) | −0.0023 (6) |
O2 | 0.0229 (6) | 0.0260 (7) | 0.0199 (6) | −0.0020 (5) | 0.0029 (5) | −0.0044 (5) |
O3 | 0.0444 (9) | 0.0275 (8) | 0.0423 (9) | −0.0093 (7) | 0.0170 (7) | 0.0005 (6) |
O4 | 0.0331 (8) | 0.0337 (8) | 0.0288 (7) | −0.0041 (6) | 0.0098 (6) | −0.0033 (6) |
N1 | 0.0197 (7) | 0.0236 (8) | 0.0244 (8) | −0.0022 (6) | 0.0043 (6) | −0.0072 (6) |
N2 | 0.0244 (8) | 0.0318 (9) | 0.0298 (9) | −0.0056 (7) | 0.0085 (7) | −0.0141 (7) |
N3 | 0.0172 (7) | 0.0217 (7) | 0.0245 (8) | −0.0035 (6) | 0.0053 (6) | −0.0058 (6) |
N4 | 0.0312 (8) | 0.0226 (8) | 0.0231 (8) | −0.0025 (6) | 0.0104 (7) | 0.0048 (6) |
N5 | 0.0441 (10) | 0.0325 (9) | 0.0217 (8) | −0.0175 (8) | 0.0039 (7) | 0.0006 (7) |
N6 | 0.0247 (8) | 0.0203 (7) | 0.0191 (7) | −0.0032 (6) | 0.0073 (6) | 0.0024 (6) |
N7 | 0.0469 (11) | 0.0411 (11) | 0.0206 (8) | −0.0018 (9) | 0.0068 (7) | 0.0036 (7) |
N8 | 0.0512 (11) | 0.0327 (10) | 0.0207 (9) | −0.0024 (8) | 0.0134 (8) | −0.0020 (7) |
N9 | 0.0309 (8) | 0.0234 (8) | 0.0233 (8) | −0.0025 (7) | 0.0093 (6) | 0.0007 (6) |
N10 | 0.0333 (8) | 0.0198 (8) | 0.0144 (7) | −0.0113 (7) | 0.0038 (6) | 0.0009 (6) |
C1 | 0.0197 (9) | 0.0251 (9) | 0.0261 (9) | −0.0025 (7) | 0.0047 (7) | −0.0079 (7) |
C2 | 0.0232 (9) | 0.0341 (11) | 0.0293 (10) | −0.0032 (8) | 0.0084 (8) | −0.0142 (8) |
C3 | 0.0212 (9) | 0.0214 (9) | 0.0241 (9) | −0.0053 (7) | 0.0078 (7) | −0.0014 (7) |
C4 | 0.0192 (8) | 0.0172 (8) | 0.0219 (9) | −0.0033 (7) | 0.0022 (7) | −0.0033 (7) |
C5 | 0.0245 (9) | 0.0305 (10) | 0.0240 (9) | −0.0068 (8) | 0.0100 (7) | −0.0066 (8) |
C6 | 0.0221 (9) | 0.0284 (10) | 0.0261 (9) | −0.0105 (8) | 0.0092 (7) | −0.0027 (8) |
C7 | 0.0236 (9) | 0.0177 (8) | 0.0167 (8) | −0.0047 (7) | 0.0025 (7) | 0.0014 (7) |
C8 | 0.0257 (9) | 0.0221 (9) | 0.0194 (9) | −0.0040 (7) | 0.0089 (7) | −0.0012 (7) |
C9 | 0.0361 (11) | 0.0332 (11) | 0.0204 (9) | 0.0007 (9) | 0.0045 (8) | 0.0029 (8) |
C10 | 0.0538 (14) | 0.0404 (13) | 0.0205 (10) | −0.0058 (10) | 0.0137 (9) | −0.0026 (9) |
C11 | 0.0259 (9) | 0.0261 (10) | 0.0153 (8) | −0.0045 (7) | 0.0051 (7) | 0.0014 (7) |
C12 | 0.0435 (11) | 0.0182 (9) | 0.0204 (9) | 0.0017 (8) | 0.0058 (8) | 0.0034 (7) |
C13 | 0.0407 (11) | 0.0198 (9) | 0.0200 (9) | 0.0020 (8) | 0.0062 (8) | −0.0014 (7) |
C14 | 0.0221 (9) | 0.0220 (9) | 0.0161 (8) | −0.0064 (7) | 0.0036 (7) | 0.0006 (7) |
C15 | 0.0331 (10) | 0.0163 (8) | 0.0219 (9) | −0.0015 (7) | 0.0045 (8) | 0.0030 (7) |
C16 | 0.0346 (10) | 0.0206 (9) | 0.0211 (9) | −0.0030 (8) | 0.0075 (8) | −0.0033 (7) |
C17 | 0.0246 (9) | 0.0241 (9) | 0.0210 (9) | 0.0008 (7) | 0.0072 (7) | 0.0048 (7) |
C18 | 0.0443 (12) | 0.0305 (11) | 0.0247 (10) | −0.0170 (9) | 0.0093 (9) | 0.0009 (8) |
C19 | 0.0255 (9) | 0.0167 (8) | 0.0200 (8) | −0.0033 (7) | 0.0093 (7) | 0.0016 (7) |
C20 | 0.0235 (9) | 0.0281 (10) | 0.0235 (9) | −0.0109 (8) | 0.0010 (7) | 0.0032 (8) |
C21 | 0.0268 (9) | 0.0291 (10) | 0.0194 (9) | −0.0075 (8) | −0.0003 (7) | 0.0069 (7) |
C22 | 0.0251 (9) | 0.0176 (9) | 0.0183 (8) | −0.0053 (7) | 0.0056 (7) | 0.0006 (7) |
C23 | 0.0214 (9) | 0.0231 (9) | 0.0208 (9) | −0.0060 (7) | 0.0016 (7) | 0.0000 (7) |
C24 | 0.0254 (9) | 0.0230 (9) | 0.0186 (9) | −0.0004 (7) | 0.0023 (7) | 0.0040 (7) |
C25 | 0.0191 (8) | 0.0259 (9) | 0.0258 (9) | −0.0053 (7) | 0.0043 (7) | −0.0043 (8) |
C26 | 0.0285 (10) | 0.0379 (11) | 0.0308 (11) | −0.0018 (9) | 0.0142 (8) | 0.0036 (9) |
C27 | 0.0347 (11) | 0.0262 (10) | 0.0272 (10) | −0.0055 (8) | 0.0124 (8) | 0.0015 (8) |
C28 | 0.0342 (11) | 0.0246 (9) | 0.0240 (9) | −0.0040 (8) | 0.0140 (8) | −0.0073 (8) |
O5 | 0.0426 (9) | 0.0274 (8) | 0.0316 (8) | 0.0073 (7) | 0.0068 (7) | −0.0019 (6) |
O6 | 0.0750 (13) | 0.0496 (11) | 0.0270 (8) | −0.0147 (10) | 0.0005 (8) | 0.0027 (8) |
Geometric parameters (Å, º) top
Cu1—O2 | 1.9696 (12) | C5—C6 | 1.384 (3) |
Cu1—O2i | 1.9696 (12) | C6—H6 | 0.9500 |
Cu1—N1i | 1.9739 (15) | C6—C7 | 1.387 (3) |
Cu1—N1 | 1.9739 (15) | C7—C8 | 1.392 (2) |
Cu2—O4 | 1.9627 (14) | C8—H8 | 0.9500 |
Cu2—O4ii | 1.9627 (14) | C9—H9 | 0.9500 |
Cu2—N4iii | 2.0090 (15) | C10—H10 | 0.9500 |
Cu2—N4iv | 2.0090 (15) | C11—C12 | 1.386 (3) |
O1—C25 | 1.233 (2) | C11—C16 | 1.384 (3) |
O2—C25 | 1.286 (2) | C12—H12 | 0.9500 |
O3—C28 | 1.239 (2) | C12—C13 | 1.385 (3) |
O4—C28 | 1.278 (3) | C13—H13 | 0.9500 |
N1—C1 | 1.327 (2) | C13—C14 | 1.391 (3) |
N1—C2 | 1.359 (2) | C14—C15 | 1.389 (3) |
N2—N3 | 1.357 (2) | C15—H15 | 0.9500 |
N2—C2 | 1.315 (2) | C15—C16 | 1.383 (3) |
N3—C1 | 1.326 (2) | C16—H16 | 0.9500 |
N3—C4 | 1.429 (2) | C17—H17 | 0.9500 |
N4—C17 | 1.328 (2) | C18—H18 | 0.9500 |
N4—C18 | 1.361 (3) | C19—C20 | 1.384 (3) |
N5—N6 | 1.352 (2) | C19—C24 | 1.381 (3) |
N5—C18 | 1.317 (3) | C20—H20 | 0.9500 |
N6—C17 | 1.339 (2) | C20—C21 | 1.386 (3) |
N6—C19 | 1.443 (2) | C21—H21 | 0.9500 |
N7—C9 | 1.322 (3) | C21—C22 | 1.395 (2) |
N7—C10 | 1.349 (3) | C22—C23 | 1.394 (2) |
N8—N9 | 1.354 (2) | C23—H23 | 0.9500 |
N8—C10 | 1.310 (3) | C23—C24 | 1.389 (3) |
N9—C9 | 1.334 (3) | C24—H24 | 0.9500 |
N9—C11 | 1.432 (2) | C25—C26 | 1.523 (3) |
N10—C7 | 1.418 (2) | C26—H26A | 0.9900 |
N10—C14 | 1.415 (2) | C26—H26B | 0.9900 |
N10—C22 | 1.415 (2) | C26—C27 | 1.521 (3) |
C1—H1 | 0.9500 | C27—H27A | 0.9900 |
C2—H2 | 0.9500 | C27—H27B | 0.9900 |
C3—H3 | 0.9500 | C27—C28 | 1.520 (3) |
C3—C4 | 1.384 (3) | O5—H5A | 0.829 (17) |
C3—C8 | 1.378 (2) | O5—H5B | 0.846 (16) |
C4—C5 | 1.382 (3) | O6—H6A | 0.814 (17) |
C5—H5 | 0.9500 | O6—H6B | 0.827 (17) |
| | | |
O2—Cu1—O2i | 180.0 | N8—C10—N7 | 115.19 (19) |
O2i—Cu1—N1 | 88.82 (6) | N8—C10—H10 | 122.4 |
O2—Cu1—N1i | 88.82 (6) | C12—C11—N9 | 119.71 (17) |
O2—Cu1—N1 | 91.18 (6) | C16—C11—N9 | 119.78 (17) |
O2i—Cu1—N1i | 91.18 (6) | C16—C11—C12 | 120.49 (17) |
N1i—Cu1—N1 | 180.0 | C11—C12—H12 | 120.2 |
O4—Cu2—O4ii | 180.0 | C13—C12—C11 | 119.51 (17) |
O4ii—Cu2—N4iv | 91.97 (6) | C13—C12—H12 | 120.2 |
O4ii—Cu2—N4iii | 88.03 (6) | C12—C13—H13 | 119.7 |
O4—Cu2—N4iv | 88.03 (6) | C12—C13—C14 | 120.52 (17) |
O4—Cu2—N4iii | 91.97 (6) | C14—C13—H13 | 119.7 |
N4iii—Cu2—N4iv | 180.00 (5) | C13—C14—N10 | 119.77 (16) |
C25—O2—Cu1 | 105.90 (11) | C15—C14—N10 | 120.95 (17) |
C28—O4—Cu2 | 108.04 (12) | C15—C14—C13 | 119.26 (17) |
C1—N1—Cu1 | 125.76 (13) | C14—C15—H15 | 119.7 |
C1—N1—C2 | 103.76 (15) | C16—C15—C14 | 120.51 (17) |
C2—N1—Cu1 | 130.38 (13) | C16—C15—H15 | 119.7 |
C2—N2—N3 | 102.84 (15) | C11—C16—H16 | 120.1 |
N2—N3—C4 | 122.44 (14) | C15—C16—C11 | 119.71 (17) |
C1—N3—N2 | 110.47 (14) | C15—C16—H16 | 120.1 |
C1—N3—C4 | 127.06 (15) | N4—C17—N6 | 108.66 (16) |
C17—N4—Cu2v | 132.61 (13) | N4—C17—H17 | 125.7 |
C17—N4—C18 | 103.74 (15) | N6—C17—H17 | 125.7 |
C18—N4—Cu2v | 123.59 (13) | N4—C18—H18 | 122.9 |
C18—N5—N6 | 102.42 (16) | N5—C18—N4 | 114.16 (17) |
N5—N6—C19 | 118.79 (14) | N5—C18—H18 | 122.9 |
C17—N6—N5 | 110.99 (15) | C20—C19—N6 | 118.07 (16) |
C17—N6—C19 | 130.19 (16) | C24—C19—N6 | 120.95 (16) |
C9—N7—C10 | 102.70 (17) | C24—C19—C20 | 120.98 (16) |
C10—N8—N9 | 102.31 (17) | C19—C20—H20 | 120.1 |
N8—N9—C11 | 120.98 (16) | C19—C20—C21 | 119.75 (17) |
C9—N9—N8 | 109.85 (16) | C21—C20—H20 | 120.1 |
C9—N9—C11 | 129.17 (17) | C20—C21—H21 | 119.8 |
C14—N10—C7 | 118.83 (14) | C20—C21—C22 | 120.41 (17) |
C14—N10—C22 | 121.32 (15) | C22—C21—H21 | 119.8 |
C22—N10—C7 | 119.49 (14) | C21—C22—N10 | 120.98 (16) |
N1—C1—H1 | 125.4 | C23—C22—N10 | 120.33 (15) |
N3—C1—N1 | 109.25 (16) | C23—C22—C21 | 118.69 (16) |
N3—C1—H1 | 125.4 | C22—C23—H23 | 119.4 |
N1—C2—H2 | 123.2 | C24—C23—C22 | 121.14 (16) |
N2—C2—N1 | 113.68 (17) | C24—C23—H23 | 119.4 |
N2—C2—H2 | 123.2 | C19—C24—C23 | 118.94 (16) |
C4—C3—H3 | 120.4 | C19—C24—H24 | 120.5 |
C8—C3—H3 | 120.4 | C23—C24—H24 | 120.5 |
C8—C3—C4 | 119.11 (16) | O1—C25—O2 | 122.76 (18) |
C3—C4—N3 | 118.72 (15) | O1—C25—C26 | 121.47 (18) |
C5—C4—N3 | 119.75 (16) | O2—C25—C26 | 115.74 (17) |
C5—C4—C3 | 121.50 (16) | C25—C26—H26A | 108.9 |
C4—C5—H5 | 120.7 | C25—C26—H26B | 108.9 |
C4—C5—C6 | 118.67 (17) | H26A—C26—H26B | 107.7 |
C6—C5—H5 | 120.7 | C27—C26—C25 | 113.22 (17) |
C5—C6—H6 | 119.7 | C27—C26—H26A | 108.9 |
C5—C6—C7 | 120.63 (17) | C27—C26—H26B | 108.9 |
C7—C6—H6 | 119.7 | C26—C27—H27A | 109.0 |
C6—C7—N10 | 120.77 (16) | C26—C27—H27B | 109.0 |
C6—C7—C8 | 119.43 (16) | H27A—C27—H27B | 107.8 |
C8—C7—N10 | 119.80 (16) | C28—C27—C26 | 112.98 (16) |
C3—C8—C7 | 120.32 (16) | C28—C27—H27A | 109.0 |
C3—C8—H8 | 119.8 | C28—C27—H27B | 109.0 |
C7—C8—H8 | 119.8 | O3—C28—O4 | 123.15 (19) |
N7—C9—N9 | 109.95 (19) | O3—C28—C27 | 120.57 (18) |
N7—C9—H9 | 125.0 | O4—C28—C27 | 116.26 (17) |
N9—C9—H9 | 125.0 | H5A—O5—H5B | 105 (2) |
N7—C10—H10 | 122.4 | H6A—O6—H6B | 106 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1/2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2 | 0.83 (2) | 2.10 (2) | 2.880 (2) | 157 (2) |
O5—H5B···N7vi | 0.85 (2) | 2.02 (2) | 2.856 (2) | 173 (2) |
O6—H6A···O5 | 0.81 (2) | 2.07 (2) | 2.857 (2) | 163 (3) |
O6—H6B···N8vii | 0.83 (2) | 2.23 (2) | 3.018 (3) | 161 (3) |
Symmetry codes: (vi) x+1, y, z+1; (vii) x+1/2, −y+1/2, z+1/2. |