Coordination polymers (CPs) have been widely studied because of their diverse and adjustable topologies and wide-ranging applications in luminescence, chemical sensors, magnetism, photocatalysis, gas adsorption and separation. In the present work, two coordination polymers, namely poly[(μ5-benzene-1,3,5-tricarboxylato-κ6O1:O1′:O3:O3:O5,O5′){μ3-1,3-bis[(1,2,4-triazol-4-yl)methyl]benzene-κ3N:N′:N′′}di-μ3-hydroxido-dicobalt(II)], [Co2(C9H3O6)(OH)(C12H12N6)]n or [Co2(btc)(OH)(mtrb)]n, (1), and poly[[diaquabis(μ3-benzene-1,3,5-tricarboxylato-κ3O1:O3:O5)bis{μ3-1,3-bis[(1,2,4-triazol-4-yl)methyl]benzene-κ3N:N′:N′′}tetra-μ3-hydroxido-tetracopper(II)] monohydrate], {[Cu4(C9H3O6)2(OH)2(C12H12N6)2(H2O)2]·H2O}n or {[Cu4(btc)2(OH)2(mtrb)2(H2O)2]·H2O}n, (2), were synthesized by the hydrothermal method using 1,3-bis[(1,2,4-triazol-4-yl)methyl]benzene (mtrb) and benzene-1,3,5-tricarboxylate (btc3−). CP (1) exhibits a (3,8)-coordinated three-dimensional (3D) network of the 3,8T38 topological type, with a point symbol of {4,5,6}2{42·56·616·72·82}, based on the tetranuclear hydroxide cobalt(II) cluster [Co4(μ3-OH)2]. CP (2) shows a (3,8)-coordinated tfz-d topology, with a point symbol of {43}2{46·618·84}, based on the tetranuclear hydroxide copper(II) cluster [Cu4(μ3-OH)2]. The different (3,8)-coordinated 3D networks based on tetranuclear hydroxide–metal clusters of (1) and (2) are controlled by the different central metal ions [CoII for (1) and CuII for (2)]. The thermal stabilities and solid-state optical diffuse-reflection spectra were measured. The energy band gaps (Eg) obtained for (1) and (2) were 2.72 and 2.29 eV, respectively. CPs (1) and (2) exhibit good photocatalytic degradation of the organic dyes methylene blue (MB) and rhodamine B (RhB) under visible-light irradiation.
Supporting information
CCDC references: 1922074; 1922073
For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXL2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Poly[(µ
5-benzene-1,3,5-tricarboxylato-
κ6O
1:O
1':O
3:O
3:O
5,O
5'){µ
3-1,3-bis[(1,2,4-triazol-4-yl)methyl]benzene-
κ3N:
N':
N''}di-µ
3-hydroxido-dicobalt(II)] (1)
top
Crystal data top
[Co2(C9H3O6)(OH)(C12H12N6)] | F(000) = 1176 |
Mr = 582.26 | Dx = 1.745 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0600 (6) Å | Cell parameters from 3893 reflections |
b = 17.1537 (9) Å | θ = 3.6–30.5° |
c = 11.7342 (5) Å | µ = 1.56 mm−1 |
β = 95.499 (4)° | T = 223 K |
V = 2215.97 (19) Å3 | Block, clear dark red |
Z = 4 | 0.50 × 0.40 × 0.20 mm |
Data collection top
Agilent Gemini Atlas diffractometer | 4583 reflections with I > 2σ(I) |
Detector resolution: 10.4471 pixels mm-1 | Rint = 0.042 |
ω scans | θmax = 31.1°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −14→16 |
Tmin = 0.479, Tmax = 0.733 | k = −24→23 |
14040 measured reflections | l = −16→10 |
6166 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0382P)2 + 0.4665P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
6166 reflections | Δρmax = 0.90 e Å−3 |
328 parameters | Δρmin = −0.59 e Å−3 |
1 restraint | |
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 | |
Co1 | 0.36873 (3) | 0.46234 (2) | 0.98933 (3) | 0.01474 (10) | |
Co2 | 0.50294 (3) | 0.56081 (2) | 0.76901 (3) | 0.01522 (10) | |
O1 | 0.68743 (19) | 0.64417 (12) | 0.96247 (15) | 0.0260 (5) | |
O2 | 0.61463 (19) | 0.65702 (12) | 0.77926 (15) | 0.0245 (5) | |
O3 | 0.84761 (17) | 0.98457 (11) | 0.65623 (14) | 0.0169 (4) | |
O4 | 0.7921 (2) | 0.87323 (13) | 0.56821 (15) | 0.0290 (5) | |
O5 | 1.00132 (18) | 0.93116 (12) | 1.08823 (14) | 0.0205 (4) | |
O6 | 0.86585 (18) | 0.86616 (13) | 1.17613 (15) | 0.0264 (5) | |
O7 | 0.45448 (17) | 0.55807 (11) | 0.92891 (14) | 0.0148 (4) | |
H7 | 0.423 (2) | 0.5920 (14) | 0.962 (2) | 0.018* | |
N1 | 0.3858 (2) | 0.40564 (15) | 0.82460 (18) | 0.0216 (5) | |
N2 | 0.4047 (2) | 0.45539 (14) | 0.73542 (18) | 0.0204 (5) | |
N3 | 0.3228 (2) | 0.34796 (15) | 0.66381 (18) | 0.0248 (6) | |
N4 | −0.1841 (2) | 0.51558 (17) | 0.0813 (2) | 0.0271 (6) | |
N5 | −0.1037 (3) | 0.5749 (2) | 0.1143 (3) | 0.0593 (10) | |
N6 | −0.0166 (3) | 0.4667 (2) | 0.1643 (2) | 0.0389 (8) | |
C1 | 0.3368 (3) | 0.34265 (19) | 0.7789 (2) | 0.0289 (7) | |
H1 | 0.314053 | 0.299153 | 0.820674 | 0.035* | |
C2 | 0.3656 (3) | 0.41960 (19) | 0.6410 (2) | 0.0255 (7) | |
H2 | 0.366968 | 0.440692 | 0.567243 | 0.031* | |
C3 | 0.2619 (3) | 0.2937 (2) | 0.5793 (3) | 0.0379 (9) | |
H3A | 0.233339 | 0.247903 | 0.618749 | 0.046* | |
H3B | 0.319774 | 0.276148 | 0.526493 | 0.046* | |
C4 | 0.1558 (3) | 0.3334 (2) | 0.5129 (3) | 0.0333 (8) | |
C5 | 0.0525 (4) | 0.3503 (3) | 0.5662 (3) | 0.0510 (11) | |
H5 | 0.047219 | 0.334792 | 0.642408 | 0.061* | |
C6 | −0.0422 (4) | 0.3896 (3) | 0.5081 (3) | 0.0608 (13) | |
H6 | −0.110778 | 0.402761 | 0.545529 | 0.073* | |
C7 | −0.0372 (3) | 0.4099 (3) | 0.3944 (3) | 0.0533 (11) | |
H7A | −0.103824 | 0.434977 | 0.354211 | 0.064* | |
C8 | 0.0649 (3) | 0.3937 (2) | 0.3395 (3) | 0.0362 (8) | |
C9 | 0.1621 (3) | 0.3563 (2) | 0.4008 (3) | 0.0315 (8) | |
H9 | 0.233309 | 0.346491 | 0.365375 | 0.038* | |
C10 | 0.0752 (3) | 0.4117 (3) | 0.2141 (3) | 0.0466 (10) | |
H10A | 0.155973 | 0.433285 | 0.206144 | 0.056* | |
H10B | 0.067843 | 0.362930 | 0.170435 | 0.056* | |
C11 | −0.1272 (3) | 0.4511 (2) | 0.1127 (3) | 0.0396 (9) | |
H11 | −0.159559 | 0.400742 | 0.100794 | 0.048* | |
C12 | −0.0036 (3) | 0.5440 (2) | 0.1640 (3) | 0.0451 (10) | |
H12 | 0.065481 | 0.571622 | 0.194280 | 0.054* | |
C13 | 0.6744 (2) | 0.68044 (16) | 0.8689 (2) | 0.0179 (6) | |
C14 | 0.7400 (2) | 0.75712 (16) | 0.8667 (2) | 0.0180 (6) | |
C15 | 0.7443 (2) | 0.80024 (16) | 0.7674 (2) | 0.0184 (6) | |
H15 | 0.706847 | 0.780866 | 0.697898 | 0.022* | |
C16 | 0.8035 (2) | 0.87194 (17) | 0.7693 (2) | 0.0163 (5) | |
C17 | 0.8555 (2) | 0.90131 (17) | 0.8730 (2) | 0.0176 (6) | |
H17 | 0.892143 | 0.950820 | 0.875918 | 0.021* | |
C18 | 0.8535 (2) | 0.85741 (17) | 0.9728 (2) | 0.0191 (6) | |
C19 | 0.7971 (3) | 0.78584 (17) | 0.9689 (2) | 0.0209 (6) | |
H19 | 0.797189 | 0.755986 | 1.036062 | 0.025* | |
C20 | 0.8145 (2) | 0.91275 (17) | 0.6562 (2) | 0.0165 (6) | |
C21 | 0.9101 (3) | 0.88669 (17) | 1.0862 (2) | 0.0198 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0181 (2) | 0.0131 (2) | 0.01287 (16) | −0.00291 (15) | 0.00032 (13) | 0.00181 (14) |
Co2 | 0.0198 (2) | 0.0144 (2) | 0.01122 (16) | −0.00216 (15) | 0.00023 (13) | 0.00083 (14) |
O1 | 0.0406 (13) | 0.0181 (12) | 0.0180 (9) | −0.0124 (9) | −0.0044 (8) | 0.0064 (8) |
O2 | 0.0362 (12) | 0.0196 (12) | 0.0165 (9) | −0.0136 (9) | −0.0041 (8) | 0.0026 (8) |
O3 | 0.0208 (10) | 0.0135 (10) | 0.0161 (8) | −0.0038 (8) | 0.0004 (7) | 0.0033 (8) |
O4 | 0.0485 (14) | 0.0232 (13) | 0.0149 (9) | −0.0146 (10) | 0.0013 (9) | −0.0001 (8) |
O5 | 0.0261 (11) | 0.0199 (11) | 0.0151 (9) | −0.0089 (9) | −0.0005 (8) | −0.0013 (8) |
O6 | 0.0321 (12) | 0.0325 (13) | 0.0149 (9) | −0.0118 (10) | 0.0028 (8) | −0.0008 (9) |
O7 | 0.0189 (10) | 0.0124 (10) | 0.0134 (8) | 0.0010 (8) | 0.0034 (7) | 0.0002 (7) |
N1 | 0.0293 (14) | 0.0211 (14) | 0.0145 (10) | −0.0064 (11) | 0.0029 (9) | 0.0008 (10) |
N2 | 0.0253 (13) | 0.0208 (14) | 0.0153 (10) | −0.0041 (10) | 0.0033 (9) | 0.0010 (10) |
N3 | 0.0333 (15) | 0.0228 (15) | 0.0177 (11) | −0.0048 (11) | −0.0004 (10) | −0.0040 (10) |
N4 | 0.0225 (13) | 0.0299 (16) | 0.0279 (12) | −0.0017 (12) | −0.0032 (10) | −0.0023 (12) |
N5 | 0.040 (2) | 0.057 (3) | 0.077 (2) | −0.0123 (18) | −0.0131 (17) | 0.0021 (19) |
N6 | 0.0276 (16) | 0.054 (2) | 0.0332 (14) | 0.0128 (15) | −0.0060 (12) | −0.0020 (14) |
C1 | 0.043 (2) | 0.0222 (18) | 0.0214 (13) | −0.0083 (14) | 0.0009 (13) | 0.0037 (13) |
C2 | 0.0293 (17) | 0.0277 (18) | 0.0186 (13) | −0.0047 (14) | −0.0026 (11) | 0.0003 (12) |
C3 | 0.053 (2) | 0.028 (2) | 0.0294 (16) | −0.0041 (17) | −0.0127 (15) | −0.0127 (15) |
C4 | 0.0342 (19) | 0.031 (2) | 0.0328 (16) | −0.0087 (15) | −0.0059 (14) | −0.0063 (15) |
C5 | 0.043 (2) | 0.071 (3) | 0.0389 (19) | −0.014 (2) | 0.0055 (17) | 0.002 (2) |
C6 | 0.033 (2) | 0.096 (4) | 0.055 (2) | −0.006 (2) | 0.0132 (18) | 0.005 (3) |
C7 | 0.028 (2) | 0.079 (4) | 0.052 (2) | 0.006 (2) | −0.0015 (16) | 0.004 (2) |
C8 | 0.0253 (17) | 0.046 (2) | 0.0360 (17) | 0.0019 (16) | −0.0022 (13) | −0.0030 (17) |
C9 | 0.0272 (17) | 0.035 (2) | 0.0310 (15) | 0.0025 (15) | −0.0032 (13) | −0.0079 (15) |
C10 | 0.033 (2) | 0.065 (3) | 0.0405 (19) | 0.0214 (19) | −0.0033 (15) | 0.0014 (19) |
C11 | 0.037 (2) | 0.036 (2) | 0.0428 (19) | 0.0040 (16) | −0.0138 (16) | −0.0023 (16) |
C12 | 0.0230 (18) | 0.045 (3) | 0.063 (2) | −0.0047 (17) | −0.0151 (17) | −0.001 (2) |
C13 | 0.0226 (14) | 0.0128 (14) | 0.0183 (12) | −0.0041 (11) | 0.0027 (10) | 0.0022 (11) |
C14 | 0.0250 (15) | 0.0129 (14) | 0.0160 (11) | −0.0062 (11) | 0.0016 (10) | 0.0001 (11) |
C15 | 0.0250 (15) | 0.0142 (15) | 0.0155 (12) | −0.0065 (12) | −0.0013 (10) | −0.0004 (11) |
C16 | 0.0196 (14) | 0.0147 (14) | 0.0144 (11) | −0.0024 (11) | 0.0008 (10) | 0.0013 (10) |
C17 | 0.0186 (14) | 0.0143 (14) | 0.0200 (12) | −0.0063 (11) | 0.0021 (10) | 0.0013 (11) |
C18 | 0.0233 (15) | 0.0189 (16) | 0.0143 (11) | −0.0039 (12) | −0.0014 (10) | 0.0020 (11) |
C19 | 0.0296 (16) | 0.0175 (15) | 0.0155 (12) | −0.0081 (12) | 0.0010 (11) | 0.0029 (11) |
C20 | 0.0173 (13) | 0.0161 (14) | 0.0158 (12) | −0.0032 (11) | 0.0001 (10) | 0.0014 (11) |
C21 | 0.0270 (15) | 0.0156 (15) | 0.0160 (12) | −0.0001 (12) | −0.0015 (10) | 0.0010 (11) |
Geometric parameters (Å, º) top
Co1—O1i | 2.027 (2) | C2—H2 | 0.9400 |
Co1—O3ii | 2.1926 (17) | C3—H3A | 0.9800 |
Co1—O7i | 2.1230 (18) | C3—H3B | 0.9800 |
Co1—O7 | 2.056 (2) | C3—C4 | 1.508 (4) |
Co1—N1 | 2.188 (2) | C4—C5 | 1.384 (5) |
Co1—N4iii | 2.163 (2) | C4—C9 | 1.381 (4) |
Co2—O2 | 2.058 (2) | C5—H5 | 0.9400 |
Co2—O3iv | 2.2213 (18) | C5—C6 | 1.370 (6) |
Co2—O5v | 2.1241 (17) | C6—H6 | 0.9400 |
Co2—O6v | 2.1770 (19) | C6—C7 | 1.386 (5) |
Co2—O7 | 2.0007 (18) | C7—H7A | 0.9400 |
Co2—N2 | 2.127 (2) | C7—C8 | 1.381 (5) |
O1—C13 | 1.258 (3) | C8—C9 | 1.391 (4) |
O2—C13 | 1.254 (3) | C8—C10 | 1.519 (5) |
O3—C20 | 1.285 (3) | C9—H9 | 0.9400 |
O4—C20 | 1.240 (3) | C10—H10A | 0.9800 |
O5—C21 | 1.263 (3) | C10—H10B | 0.9800 |
O6—C21 | 1.255 (3) | C11—H11 | 0.9400 |
O7—H7 | 0.800 (17) | C12—H12 | 0.9400 |
N1—N2 | 1.382 (3) | C13—C14 | 1.504 (4) |
N1—C1 | 1.301 (4) | C14—C15 | 1.384 (3) |
N2—C2 | 1.303 (3) | C14—C19 | 1.390 (4) |
N3—C1 | 1.348 (3) | C15—H15 | 0.9400 |
N3—C2 | 1.353 (4) | C15—C16 | 1.392 (4) |
N3—C3 | 1.474 (4) | C16—C17 | 1.390 (3) |
N4—N5 | 1.382 (4) | C16—C20 | 1.516 (4) |
N4—C11 | 1.308 (4) | C17—H17 | 0.9400 |
N5—C12 | 1.312 (5) | C17—C18 | 1.394 (4) |
N6—C10 | 1.465 (4) | C18—C19 | 1.376 (4) |
N6—C11 | 1.339 (4) | C18—C21 | 1.502 (3) |
N6—C12 | 1.333 (5) | C19—H19 | 0.9400 |
C1—H1 | 0.9400 | | |
| | | |
O1i—Co1—O3ii | 93.64 (8) | N3—C2—H2 | 124.6 |
O1i—Co1—O7i | 91.08 (8) | N3—C3—H3A | 109.6 |
O1i—Co1—O7 | 168.41 (9) | N3—C3—H3B | 109.6 |
O1i—Co1—N1 | 84.29 (8) | N3—C3—C4 | 110.2 (3) |
O1i—Co1—N4iii | 87.79 (10) | H3A—C3—H3B | 108.1 |
O7i—Co1—O3ii | 80.63 (7) | C4—C3—H3A | 109.6 |
O7—Co1—O3ii | 93.92 (7) | C4—C3—H3B | 109.6 |
O7—Co1—O7i | 81.50 (8) | C5—C4—C3 | 119.8 (3) |
O7i—Co1—N1 | 99.93 (8) | C9—C4—C3 | 120.8 (3) |
O7—Co1—N1 | 88.21 (8) | C9—C4—C5 | 119.4 (3) |
O7—Co1—N4iii | 100.25 (9) | C4—C5—H5 | 119.9 |
O7i—Co1—N4iii | 175.68 (8) | C6—C5—C4 | 120.1 (4) |
N1—Co1—O3ii | 177.86 (8) | C6—C5—H5 | 119.9 |
N4iii—Co1—O3ii | 95.28 (8) | C5—C6—H6 | 119.9 |
N4iii—Co1—N1 | 84.12 (9) | C5—C6—C7 | 120.3 (4) |
O2—Co2—O3iv | 91.68 (8) | C7—C6—H6 | 119.9 |
O2—Co2—O5v | 87.36 (8) | C6—C7—H7A | 119.7 |
O2—Co2—O6v | 87.31 (8) | C8—C7—C6 | 120.5 (3) |
O2—Co2—N2 | 170.31 (9) | C8—C7—H7A | 119.7 |
O5v—Co2—O3iv | 111.55 (7) | C7—C8—C9 | 118.6 (3) |
O5v—Co2—O6v | 61.57 (7) | C7—C8—C10 | 123.4 (3) |
O5v—Co2—N2 | 85.12 (8) | C9—C8—C10 | 118.0 (3) |
O6v—Co2—O3iv | 173.08 (7) | C4—C9—C8 | 121.0 (3) |
O7—Co2—O2 | 100.21 (8) | C4—C9—H9 | 119.5 |
O7—Co2—O3iv | 82.64 (7) | C8—C9—H9 | 119.5 |
O7—Co2—O5v | 163.89 (8) | N6—C10—C8 | 113.8 (3) |
O7—Co2—O6v | 104.28 (8) | N6—C10—H10A | 108.8 |
O7—Co2—N2 | 88.60 (8) | N6—C10—H10B | 108.8 |
N2—Co2—O3iv | 85.43 (8) | C8—C10—H10A | 108.8 |
N2—Co2—O6v | 94.44 (9) | C8—C10—H10B | 108.8 |
C13—O1—Co1i | 132.57 (18) | H10A—C10—H10B | 107.7 |
C13—O2—Co2 | 124.86 (17) | N4—C11—N6 | 110.6 (3) |
Co1vi—O3—Co2vii | 88.24 (7) | N4—C11—H11 | 124.7 |
C20—O3—Co1vi | 116.93 (15) | N6—C11—H11 | 124.7 |
C20—O3—Co2vii | 139.95 (16) | N5—C12—N6 | 108.4 (3) |
C21—O5—Co2viii | 89.32 (15) | N5—C12—H12 | 125.8 |
C21—O6—Co2viii | 87.17 (17) | N6—C12—H12 | 125.8 |
Co1—O7—Co1i | 98.50 (8) | O1—C13—C14 | 115.6 (2) |
Co1i—O7—H7 | 109 (2) | O2—C13—O1 | 125.5 (3) |
Co1—O7—H7 | 100 (2) | O2—C13—C14 | 118.9 (2) |
Co2—O7—Co1i | 96.30 (8) | C15—C14—C13 | 122.5 (2) |
Co2—O7—Co1 | 121.07 (9) | C15—C14—C19 | 119.1 (3) |
Co2—O7—H7 | 128 (2) | C19—C14—C13 | 118.4 (2) |
N2—N1—Co1 | 115.26 (18) | C14—C15—H15 | 119.6 |
C1—N1—Co1 | 131.7 (2) | C14—C15—C16 | 120.8 (2) |
C1—N1—N2 | 106.7 (2) | C16—C15—H15 | 119.6 |
N1—N2—Co2 | 119.77 (16) | C15—C16—C20 | 118.1 (2) |
C2—N2—Co2 | 132.8 (2) | C17—C16—C15 | 119.2 (2) |
C2—N2—N1 | 106.9 (2) | C17—C16—C20 | 122.6 (2) |
C1—N3—C2 | 104.5 (2) | C16—C17—H17 | 120.0 |
C1—N3—C3 | 129.2 (3) | C16—C17—C18 | 120.1 (3) |
C2—N3—C3 | 125.9 (2) | C18—C17—H17 | 120.0 |
N5—N4—Co1iii | 122.5 (2) | C17—C18—C21 | 121.6 (3) |
C11—N4—Co1iii | 131.8 (2) | C19—C18—C17 | 119.8 (2) |
C11—N4—N5 | 105.3 (3) | C19—C18—C21 | 118.5 (2) |
C12—N5—N4 | 108.7 (3) | C14—C19—H19 | 119.6 |
C11—N6—C10 | 128.3 (4) | C18—C19—C14 | 120.8 (2) |
C12—N6—C10 | 124.8 (3) | C18—C19—H19 | 119.6 |
C12—N6—C11 | 106.9 (3) | O3—C20—C16 | 119.3 (2) |
N1—C1—N3 | 111.1 (3) | O4—C20—O3 | 123.9 (2) |
N1—C1—H1 | 124.5 | O4—C20—C16 | 116.8 (3) |
N3—C1—H1 | 124.5 | O5—C21—C18 | 118.9 (2) |
N2—C2—N3 | 110.7 (3) | O6—C21—O5 | 121.9 (2) |
N2—C2—H2 | 124.6 | O6—C21—C18 | 119.2 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x, −y+1, −z+1; (iv) −x+3/2, y−1/2, −z+3/2; (v) x−1/2, −y+3/2, z−1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) −x+3/2, y+1/2, −z+3/2; (viii) x+1/2, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7···O4ii | 0.80 (2) | 2.08 (2) | 2.802 (3) | 149 (3) |
C2—H2···O5iv | 0.94 | 2.45 | 3.194 (4) | 136 |
Symmetry codes: (ii) x−1/2, −y+3/2, z+1/2; (iv) −x+3/2, y−1/2, −z+3/2. |
Poly[[diaquabis(µ
3-benzene-1,3,5-tricarboxylato-
κ3O1:
O3:
O5)bis{µ
3-1,3-bis[(1,2,4-triazol-4-yl)methyl]benzene-
κ3N:
N':
N''}tetra-µ
3-hydroxido-tetracopper(II)]
monohydrate] (2)
top
Crystal data top
[Cu4(C9H3O6)2(OH)2(C12H12N6)2(H2O)2]·H2O | Z = 1 |
Mr = 1237.00 | F(000) = 626 |
Triclinic, P1 | Dx = 1.683 Mg m−3 |
a = 10.9425 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4580 (9) Å | Cell parameters from 10482 reflections |
c = 11.6193 (10) Å | θ = 3.0–26.8° |
α = 89.524 (7)° | µ = 1.80 mm−1 |
β = 69.945 (8)° | T = 223 K |
γ = 64.669 (8)° | Block, blue |
V = 1220.4 (2) Å3 | 0.50 × 0.20 × 0.10 mm |
Data collection top
Agilent Gemini Atlas diffractometer | 4660 reflections with I > 2σ(I) |
Detector resolution: 10.4471 pixels mm-1 | Rint = 0.041 |
MoKα scans | θmax = 30.3°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −15→15 |
Tmin = 0.472, Tmax = 0.827 | k = −14→15 |
11737 measured reflections | l = −16→16 |
6238 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0648P)2 + 1.6446P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6238 reflections | Δρmax = 1.30 e Å−3 |
346 parameters | Δρmin = −0.71 e Å−3 |
1 restraint | |
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 | Occ. (<1) |
Cu1 | 0.60753 (5) | 0.05021 (4) | 0.00333 (4) | 0.01792 (13) | |
Cu2 | 0.29483 (5) | 0.28537 (4) | 0.16439 (4) | 0.02078 (14) | |
O1 | 0.6860 (3) | −0.0715 (3) | 0.1076 (2) | 0.0233 (6) | |
O2 | 0.6440 (4) | 0.0851 (3) | 0.2499 (3) | 0.0387 (8) | |
O3 | 0.6683 (4) | −0.0601 (3) | 0.6542 (2) | 0.0390 (8) | |
O4 | 0.7830 (3) | −0.2751 (3) | 0.6582 (2) | 0.0354 (8) | |
O5 | 1.1629 (3) | −0.5290 (3) | 0.2064 (3) | 0.0303 (7) | |
O6 | 1.0027 (4) | −0.5596 (3) | 0.1464 (3) | 0.0382 (8) | |
O7 | 0.4103 (3) | 0.0994 (3) | 0.1136 (2) | 0.0187 (5) | |
H7 | 0.400 (5) | 0.073 (4) | 0.187 (2) | 0.022* | |
O8 | 0.5001 (4) | 0.3075 (4) | 0.1694 (4) | 0.0556 (10) | |
H8A | 0.547338 | 0.256973 | 0.207794 | 0.067* | |
H8B | 0.554028 | 0.328483 | 0.116034 | 0.067* | |
N1 | 0.5135 (3) | 0.1945 (3) | −0.0847 (3) | 0.0204 (7) | |
N2 | 0.3755 (3) | 0.2917 (3) | −0.0186 (3) | 0.0205 (7) | |
N3 | 0.4306 (4) | 0.3096 (3) | −0.2141 (3) | 0.0222 (7) | |
N4 | 1.1890 (4) | 0.0015 (3) | −0.8890 (3) | 0.0233 (7) | |
N5 | 1.1257 (4) | −0.0674 (4) | −0.8157 (4) | 0.0437 (11) | |
N6 | 0.9609 (4) | 0.1350 (4) | −0.7871 (3) | 0.0281 (8) | |
C1 | 0.7546 (5) | 0.3061 (4) | −0.6113 (4) | 0.0277 (9) | |
C2 | 0.6266 (4) | 0.3024 (4) | −0.5362 (4) | 0.0237 (8) | |
H2 | 0.585024 | 0.261523 | −0.569702 | 0.028* | |
C3 | 0.5601 (5) | 0.3591 (4) | −0.4117 (4) | 0.0262 (9) | |
C4 | 0.6209 (6) | 0.4198 (5) | −0.3640 (4) | 0.0402 (12) | |
H4 | 0.574373 | 0.460578 | −0.280568 | 0.048* | |
C5 | 0.7499 (6) | 0.4217 (6) | −0.4375 (5) | 0.0481 (14) | |
H5 | 0.791729 | 0.461979 | −0.403661 | 0.058* | |
C6 | 0.8171 (5) | 0.3636 (5) | −0.5616 (4) | 0.0373 (11) | |
H6 | 0.905270 | 0.363454 | −0.611606 | 0.045* | |
C7 | 0.8186 (5) | 0.2542 (5) | −0.7485 (4) | 0.0318 (10) | |
H7A | 0.749681 | 0.234054 | −0.769626 | 0.038* | |
H7B | 0.831634 | 0.322435 | −0.795128 | 0.038* | |
C8 | 0.4206 (5) | 0.3545 (5) | −0.3322 (4) | 0.0287 (9) | |
H8C | 0.338046 | 0.441688 | −0.314364 | 0.034* | |
H8D | 0.403775 | 0.294444 | −0.377238 | 0.034* | |
C9 | 1.0874 (4) | 0.1225 (4) | −0.8691 (4) | 0.0260 (9) | |
H9 | 1.101886 | 0.190620 | −0.907319 | 0.031* | |
C10 | 0.9877 (5) | 0.0154 (5) | −0.7547 (5) | 0.0444 (13) | |
H10 | 0.918324 | −0.005545 | −0.697363 | 0.053* | |
C11 | 0.5431 (4) | 0.2069 (4) | −0.2022 (3) | 0.0228 (8) | |
H11 | 0.630028 | 0.151874 | −0.268058 | 0.027* | |
C12 | 0.3276 (4) | 0.3605 (4) | −0.0985 (3) | 0.0228 (8) | |
H12 | 0.236111 | 0.433592 | −0.078365 | 0.027* | |
C13 | 0.7562 (4) | −0.1363 (4) | 0.2755 (3) | 0.0191 (7) | |
C14 | 0.7230 (4) | −0.1096 (4) | 0.4022 (3) | 0.0224 (8) | |
H14 | 0.656798 | −0.024619 | 0.445947 | 0.027* | |
C15 | 0.7866 (4) | −0.2071 (4) | 0.4649 (3) | 0.0220 (8) | |
C16 | 0.8902 (4) | −0.3312 (4) | 0.3995 (3) | 0.0228 (8) | |
H16 | 0.936240 | −0.396329 | 0.441104 | 0.027* | |
C17 | 0.9260 (4) | −0.3592 (4) | 0.2718 (3) | 0.0207 (8) | |
C18 | 0.8574 (4) | −0.2623 (4) | 0.2110 (3) | 0.0191 (8) | |
H18 | 0.879322 | −0.281738 | 0.125747 | 0.023* | |
C19 | 0.6892 (4) | −0.0309 (4) | 0.2074 (3) | 0.0215 (8) | |
C20 | 0.7431 (5) | −0.1763 (4) | 0.6041 (3) | 0.0266 (9) | |
C21 | 1.0368 (4) | −0.4936 (4) | 0.2022 (3) | 0.0216 (8) | |
O9 | 1.2981 (11) | −0.3602 (8) | −0.9392 (8) | 0.072 (3) | 0.5 |
H9A | 1.249026 | −0.413917 | −0.890857 | 0.087* | 0.5 |
H9B | 1.236626 | −0.260017 | −0.898256 | 0.087* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0169 (2) | 0.0165 (2) | 0.0141 (2) | −0.00314 (18) | −0.00457 (18) | 0.00179 (16) |
Cu2 | 0.0211 (3) | 0.0157 (2) | 0.0132 (2) | 0.00198 (18) | −0.00560 (19) | −0.00255 (17) |
O1 | 0.0231 (14) | 0.0207 (14) | 0.0181 (12) | −0.0018 (11) | −0.0089 (11) | 0.0029 (10) |
O2 | 0.058 (2) | 0.0181 (16) | 0.0437 (18) | −0.0087 (15) | −0.0337 (17) | 0.0049 (13) |
O3 | 0.058 (2) | 0.0227 (16) | 0.0162 (13) | −0.0050 (15) | −0.0084 (14) | −0.0019 (11) |
O4 | 0.0411 (18) | 0.0254 (16) | 0.0128 (12) | 0.0054 (13) | −0.0061 (13) | −0.0014 (11) |
O5 | 0.0260 (15) | 0.0198 (15) | 0.0301 (15) | 0.0042 (12) | −0.0122 (13) | −0.0070 (12) |
O6 | 0.0367 (18) | 0.0263 (17) | 0.0409 (17) | −0.0077 (14) | −0.0105 (15) | −0.0084 (14) |
O7 | 0.0222 (13) | 0.0165 (13) | 0.0103 (11) | −0.0040 (11) | −0.0043 (10) | −0.0003 (9) |
O8 | 0.061 (2) | 0.036 (2) | 0.087 (3) | −0.0160 (19) | −0.056 (2) | 0.0111 (19) |
N1 | 0.0209 (16) | 0.0146 (15) | 0.0205 (15) | −0.0055 (13) | −0.0054 (13) | 0.0021 (12) |
N2 | 0.0186 (16) | 0.0144 (15) | 0.0182 (15) | −0.0011 (12) | −0.0033 (13) | −0.0010 (12) |
N3 | 0.0209 (16) | 0.0207 (17) | 0.0160 (14) | −0.0047 (13) | −0.0028 (13) | 0.0051 (12) |
N4 | 0.0203 (16) | 0.0204 (17) | 0.0263 (16) | −0.0092 (14) | −0.0054 (14) | 0.0037 (13) |
N5 | 0.034 (2) | 0.033 (2) | 0.055 (3) | −0.0160 (19) | −0.006 (2) | 0.0118 (19) |
N6 | 0.0195 (17) | 0.0279 (19) | 0.0292 (18) | −0.0078 (15) | −0.0044 (15) | 0.0034 (14) |
C1 | 0.026 (2) | 0.023 (2) | 0.026 (2) | −0.0066 (17) | −0.0070 (17) | 0.0046 (16) |
C2 | 0.023 (2) | 0.0192 (19) | 0.0245 (19) | −0.0048 (16) | −0.0100 (16) | 0.0041 (15) |
C3 | 0.027 (2) | 0.022 (2) | 0.0223 (18) | −0.0064 (17) | −0.0075 (17) | 0.0073 (15) |
C4 | 0.052 (3) | 0.045 (3) | 0.027 (2) | −0.028 (3) | −0.010 (2) | 0.000 (2) |
C5 | 0.057 (3) | 0.062 (4) | 0.041 (3) | −0.043 (3) | −0.015 (3) | 0.005 (2) |
C6 | 0.030 (2) | 0.050 (3) | 0.034 (2) | −0.023 (2) | −0.008 (2) | 0.010 (2) |
C7 | 0.020 (2) | 0.036 (3) | 0.026 (2) | −0.0052 (18) | −0.0043 (17) | 0.0025 (18) |
C8 | 0.026 (2) | 0.037 (2) | 0.0210 (19) | −0.0114 (19) | −0.0098 (17) | 0.0120 (17) |
C9 | 0.0184 (19) | 0.026 (2) | 0.0232 (19) | −0.0057 (16) | −0.0020 (16) | 0.0032 (16) |
C10 | 0.028 (2) | 0.034 (3) | 0.057 (3) | −0.013 (2) | −0.001 (2) | 0.017 (2) |
C11 | 0.0227 (19) | 0.0168 (18) | 0.0184 (17) | −0.0035 (15) | −0.0027 (16) | 0.0036 (14) |
C12 | 0.0216 (19) | 0.0203 (19) | 0.0198 (17) | −0.0033 (16) | −0.0082 (16) | 0.0043 (14) |
C13 | 0.0195 (18) | 0.0173 (18) | 0.0182 (17) | −0.0066 (15) | −0.0064 (15) | 0.0022 (14) |
C14 | 0.0206 (19) | 0.0196 (19) | 0.0172 (17) | −0.0031 (15) | −0.0034 (15) | −0.0021 (14) |
C15 | 0.0206 (19) | 0.024 (2) | 0.0142 (16) | −0.0054 (16) | −0.0046 (15) | 0.0003 (14) |
C16 | 0.025 (2) | 0.0200 (19) | 0.0164 (17) | −0.0036 (16) | −0.0078 (16) | 0.0020 (14) |
C17 | 0.0169 (18) | 0.0202 (19) | 0.0154 (16) | −0.0019 (15) | −0.0036 (14) | −0.0005 (14) |
C18 | 0.0188 (18) | 0.0197 (18) | 0.0123 (15) | −0.0044 (15) | −0.0039 (14) | 0.0000 (13) |
C19 | 0.0193 (18) | 0.0209 (19) | 0.0209 (17) | −0.0063 (15) | −0.0073 (15) | 0.0051 (14) |
C20 | 0.026 (2) | 0.028 (2) | 0.0155 (17) | −0.0031 (17) | −0.0067 (16) | 0.0003 (15) |
C21 | 0.024 (2) | 0.0167 (18) | 0.0131 (16) | −0.0021 (15) | −0.0040 (15) | 0.0029 (13) |
O9 | 0.112 (7) | 0.059 (5) | 0.063 (5) | −0.075 (6) | −0.005 (5) | 0.002 (4) |
Geometric parameters (Å, º) top
Cu1—Cu1i | 3.0515 (10) | C1—C6 | 1.377 (7) |
Cu1—O1 | 1.952 (3) | C1—C7 | 1.509 (6) |
Cu1—O7i | 2.308 (3) | C2—H2 | 0.9400 |
Cu1—O7 | 1.921 (3) | C2—C3 | 1.390 (5) |
Cu1—N1 | 2.019 (3) | C3—C4 | 1.374 (7) |
Cu1—N4ii | 1.982 (3) | C3—C8 | 1.512 (6) |
Cu2—O4iii | 1.966 (3) | C4—H4 | 0.9400 |
Cu2—O5iv | 1.937 (3) | C4—C5 | 1.387 (7) |
Cu2—O7 | 1.921 (3) | C5—H5 | 0.9400 |
Cu2—O8 | 2.385 (4) | C5—C6 | 1.390 (7) |
Cu2—N2 | 2.018 (3) | C6—H6 | 0.9400 |
O1—C19 | 1.271 (5) | C7—H7A | 0.9800 |
O2—C19 | 1.240 (5) | C7—H7B | 0.9800 |
O3—C20 | 1.239 (5) | C8—H8C | 0.9800 |
O4—C20 | 1.273 (5) | C8—H8D | 0.9800 |
O5—C21 | 1.280 (5) | C9—H9 | 0.9400 |
O6—C21 | 1.244 (5) | C10—H10 | 0.9400 |
O7—H7 | 0.891 (10) | C11—H11 | 0.9400 |
O8—H8A | 0.8369 | C12—H12 | 0.9400 |
O8—H8B | 0.8113 | C13—C14 | 1.392 (5) |
N1—N2 | 1.375 (4) | C13—C18 | 1.398 (5) |
N1—C11 | 1.312 (5) | C13—C19 | 1.498 (5) |
N2—C12 | 1.313 (5) | C14—H14 | 0.9400 |
N3—C8 | 1.484 (5) | C14—C15 | 1.389 (6) |
N3—C11 | 1.340 (5) | C15—C16 | 1.390 (5) |
N3—C12 | 1.352 (5) | C15—C20 | 1.518 (5) |
N4—N5 | 1.371 (5) | C16—H16 | 0.9400 |
N4—C9 | 1.312 (5) | C16—C17 | 1.400 (5) |
N5—C10 | 1.317 (6) | C17—C18 | 1.390 (5) |
N6—C7 | 1.484 (5) | C17—C21 | 1.499 (5) |
N6—C9 | 1.331 (5) | C18—H18 | 0.9400 |
N6—C10 | 1.353 (6) | O9—H9A | 1.0263 |
C1—C2 | 1.393 (6) | O9—H9B | 1.0606 |
| | | |
O1—Cu1—Cu1i | 95.19 (9) | C3—C4—H4 | 119.6 |
O1—Cu1—O7i | 95.32 (11) | C3—C4—C5 | 120.8 (4) |
O1—Cu1—N1 | 172.47 (12) | C5—C4—H4 | 119.6 |
O1—Cu1—N4ii | 88.15 (13) | C4—C5—H5 | 120.3 |
O7—Cu1—Cu1i | 49.12 (8) | C4—C5—C6 | 119.5 (5) |
O7i—Cu1—Cu1i | 39.00 (6) | C6—C5—H5 | 120.3 |
O7—Cu1—O1 | 91.85 (11) | C1—C6—C5 | 120.1 (4) |
O7—Cu1—O7i | 88.11 (9) | C1—C6—H6 | 119.9 |
O7—Cu1—N1 | 84.31 (12) | C5—C6—H6 | 119.9 |
O7—Cu1—N4ii | 179.60 (13) | N6—C7—C1 | 113.0 (4) |
N1—Cu1—Cu1i | 87.20 (9) | N6—C7—H7A | 109.0 |
N1—Cu1—O7i | 91.03 (11) | N6—C7—H7B | 109.0 |
N4ii—Cu1—Cu1i | 130.49 (10) | C1—C7—H7A | 109.0 |
N4ii—Cu1—O7i | 91.49 (12) | C1—C7—H7B | 109.0 |
N4ii—Cu1—N1 | 95.74 (13) | H7A—C7—H7B | 107.8 |
O4iii—Cu2—O8 | 95.54 (15) | N3—C8—C3 | 110.1 (3) |
O4iii—Cu2—N2 | 178.71 (13) | N3—C8—H8C | 109.6 |
O5iv—Cu2—O4iii | 87.65 (12) | N3—C8—H8D | 109.6 |
O5iv—Cu2—O8 | 95.44 (13) | C3—C8—H8C | 109.6 |
O5iv—Cu2—N2 | 93.46 (13) | C3—C8—H8D | 109.6 |
O7—Cu2—O4iii | 94.57 (11) | H8C—C8—H8D | 108.2 |
O7—Cu2—O5iv | 172.97 (12) | N4—C9—N6 | 110.4 (4) |
O7—Cu2—O8 | 90.99 (12) | N4—C9—H9 | 124.8 |
O7—Cu2—N2 | 84.25 (11) | N6—C9—H9 | 124.8 |
N2—Cu2—O8 | 85.00 (14) | N5—C10—N6 | 109.7 (4) |
C19—O1—Cu1 | 121.2 (3) | N5—C10—H10 | 125.2 |
C20—O4—Cu2iii | 128.3 (2) | N6—C10—H10 | 125.2 |
C21—O5—Cu2v | 116.8 (3) | N1—C11—N3 | 109.7 (3) |
Cu1—O7—Cu1i | 91.89 (9) | N1—C11—H11 | 125.1 |
Cu1i—O7—H7 | 105 (3) | N3—C11—H11 | 125.1 |
Cu1—O7—H7 | 116 (3) | N2—C12—N3 | 109.3 (3) |
Cu2—O7—Cu1 | 113.05 (13) | N2—C12—H12 | 125.4 |
Cu2—O7—Cu1i | 131.57 (14) | N3—C12—H12 | 125.4 |
Cu2—O7—H7 | 101 (3) | C14—C13—C18 | 119.0 (4) |
Cu2—O8—H8A | 116.6 | C14—C13—C19 | 120.9 (3) |
Cu2—O8—H8B | 127.6 | C18—C13—C19 | 120.0 (3) |
H8A—O8—H8B | 108.8 | C13—C14—H14 | 119.6 |
N2—N1—Cu1 | 118.2 (2) | C15—C14—C13 | 120.8 (3) |
C11—N1—Cu1 | 133.2 (3) | C15—C14—H14 | 119.6 |
C11—N1—N2 | 107.2 (3) | C14—C15—C16 | 119.8 (3) |
N1—N2—Cu2 | 115.5 (2) | C14—C15—C20 | 119.5 (3) |
C12—N2—Cu2 | 136.9 (3) | C16—C15—C20 | 120.7 (4) |
C12—N2—N1 | 107.3 (3) | C15—C16—H16 | 120.0 |
C11—N3—C8 | 126.2 (3) | C15—C16—C17 | 120.0 (4) |
C11—N3—C12 | 106.4 (3) | C17—C16—H16 | 120.0 |
C12—N3—C8 | 127.3 (3) | C16—C17—C21 | 119.7 (3) |
N5—N4—Cu1ii | 131.8 (3) | C18—C17—C16 | 119.6 (3) |
C9—N4—Cu1ii | 120.9 (3) | C18—C17—C21 | 120.6 (3) |
C9—N4—N5 | 107.3 (3) | C13—C18—H18 | 119.7 |
C10—N5—N4 | 106.9 (4) | C17—C18—C13 | 120.6 (3) |
C9—N6—C7 | 126.1 (4) | C17—C18—H18 | 119.7 |
C9—N6—C10 | 105.9 (4) | O1—C19—C13 | 115.0 (3) |
C10—N6—C7 | 127.9 (4) | O2—C19—O1 | 125.7 (4) |
C2—C1—C7 | 119.4 (4) | O2—C19—C13 | 119.4 (4) |
C6—C1—C2 | 120.0 (4) | O3—C20—O4 | 126.6 (4) |
C6—C1—C7 | 120.6 (4) | O3—C20—C15 | 117.8 (4) |
C1—C2—H2 | 120.0 | O4—C20—C15 | 115.5 (3) |
C3—C2—C1 | 120.0 (4) | O5—C21—C17 | 113.9 (4) |
C3—C2—H2 | 120.0 | O6—C21—O5 | 125.9 (4) |
C2—C3—C8 | 119.0 (4) | O6—C21—C17 | 120.2 (4) |
C4—C3—C2 | 119.5 (4) | H9A—O9—H9B | 110.4 |
C4—C3—C8 | 121.4 (4) | | |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z−1; (iii) −x+1, −y, −z+1; (iv) x−1, y+1, z; (v) x+1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7···O3iii | 0.89 (1) | 1.77 (2) | 2.635 (4) | 164 (4) |
O8—H8A···O2 | 0.84 | 1.95 | 2.718 (5) | 153 |
O8—H8B···O9ii | 0.81 | 2.28 | 3.075 (8) | 168 |
O9—H9A···O5vi | 1.03 | 2.05 | 3.078 (7) | 177 |
O9—H9B···N5 | 1.06 | 2.05 | 3.112 (9) | 177 |
Symmetry codes: (ii) −x+2, −y, −z−1; (iii) −x+1, −y, −z+1; (vi) x, y, z−1. |