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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 [Co43-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 [Cu43-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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961900826X/ky3169sup1.cif
Contains datablocks 1, 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961900826X/ky3169cobtc504sup2.hkl
Contains datablock cobtc504

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961900826X/ky3169cubtcmtrb529sup3.hkl
Contains datablock cubtcmtrb529

CCDC references: 1922074; 1922073

Computing details top

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[(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)] (1) top
Crystal data top
[Co2(C9H3O6)(OH)(C12H12N6)]F(000) = 1176
Mr = 582.26Dx = 1.745 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.0600 (6) ÅCell parameters from 3893 reflections
b = 17.1537 (9) Åθ = 3.6–30.5°
c = 11.7342 (5) ŵ = 1.56 mm1
β = 95.499 (4)°T = 223 K
V = 2215.97 (19) Å3Block, clear dark red
Z = 40.50 × 0.40 × 0.20 mm
Data collection top
Agilent Gemini Atlas
diffractometer
4583 reflections with I > 2σ(I)
Detector resolution: 10.4471 pixels mm-1Rint = 0.042
ω scansθmax = 31.1°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 1416
Tmin = 0.479, Tmax = 0.733k = 2423
14040 measured reflectionsl = 1610
6166 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H 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 reflectionsΔρmax = 0.90 e Å3
328 parametersΔρmin = 0.59 e Å3
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
xyzUiso*/Ueq
Co10.36873 (3)0.46234 (2)0.98933 (3)0.01474 (10)
Co20.50294 (3)0.56081 (2)0.76901 (3)0.01522 (10)
O10.68743 (19)0.64417 (12)0.96247 (15)0.0260 (5)
O20.61463 (19)0.65702 (12)0.77926 (15)0.0245 (5)
O30.84761 (17)0.98457 (11)0.65623 (14)0.0169 (4)
O40.7921 (2)0.87323 (13)0.56821 (15)0.0290 (5)
O51.00132 (18)0.93116 (12)1.08823 (14)0.0205 (4)
O60.86585 (18)0.86616 (13)1.17613 (15)0.0264 (5)
O70.45448 (17)0.55807 (11)0.92891 (14)0.0148 (4)
H70.423 (2)0.5920 (14)0.962 (2)0.018*
N10.3858 (2)0.40564 (15)0.82460 (18)0.0216 (5)
N20.4047 (2)0.45539 (14)0.73542 (18)0.0204 (5)
N30.3228 (2)0.34796 (15)0.66381 (18)0.0248 (6)
N40.1841 (2)0.51558 (17)0.0813 (2)0.0271 (6)
N50.1037 (3)0.5749 (2)0.1143 (3)0.0593 (10)
N60.0166 (3)0.4667 (2)0.1643 (2)0.0389 (8)
C10.3368 (3)0.34265 (19)0.7789 (2)0.0289 (7)
H10.3140530.2991530.8206740.035*
C20.3656 (3)0.41960 (19)0.6410 (2)0.0255 (7)
H20.3669680.4406920.5672430.031*
C30.2619 (3)0.2937 (2)0.5793 (3)0.0379 (9)
H3A0.2333390.2479030.6187490.046*
H3B0.3197740.2761480.5264930.046*
C40.1558 (3)0.3334 (2)0.5129 (3)0.0333 (8)
C50.0525 (4)0.3503 (3)0.5662 (3)0.0510 (11)
H50.0472190.3347920.6424080.061*
C60.0422 (4)0.3896 (3)0.5081 (3)0.0608 (13)
H60.1107780.4027610.5455290.073*
C70.0372 (3)0.4099 (3)0.3944 (3)0.0533 (11)
H7A0.1038240.4349770.3542110.064*
C80.0649 (3)0.3937 (2)0.3395 (3)0.0362 (8)
C90.1621 (3)0.3563 (2)0.4008 (3)0.0315 (8)
H90.2333090.3464910.3653750.038*
C100.0752 (3)0.4117 (3)0.2141 (3)0.0466 (10)
H10A0.1559730.4332850.2061440.056*
H10B0.0678430.3629300.1704350.056*
C110.1272 (3)0.4511 (2)0.1127 (3)0.0396 (9)
H110.1595590.4007420.1007940.048*
C120.0036 (3)0.5440 (2)0.1640 (3)0.0451 (10)
H120.0654810.5716220.1942800.054*
C130.6744 (2)0.68044 (16)0.8689 (2)0.0179 (6)
C140.7400 (2)0.75712 (16)0.8667 (2)0.0180 (6)
C150.7443 (2)0.80024 (16)0.7674 (2)0.0184 (6)
H150.7068470.7808660.6978980.022*
C160.8035 (2)0.87194 (17)0.7693 (2)0.0163 (5)
C170.8555 (2)0.90131 (17)0.8730 (2)0.0176 (6)
H170.8921430.9508200.8759180.021*
C180.8535 (2)0.85741 (17)0.9728 (2)0.0191 (6)
C190.7971 (3)0.78584 (17)0.9689 (2)0.0209 (6)
H190.7971890.7559861.0360620.025*
C200.8145 (2)0.91275 (17)0.6562 (2)0.0165 (6)
C210.9101 (3)0.88669 (17)1.0862 (2)0.0198 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0181 (2)0.0131 (2)0.01287 (16)0.00291 (15)0.00032 (13)0.00181 (14)
Co20.0198 (2)0.0144 (2)0.01122 (16)0.00216 (15)0.00023 (13)0.00083 (14)
O10.0406 (13)0.0181 (12)0.0180 (9)0.0124 (9)0.0044 (8)0.0064 (8)
O20.0362 (12)0.0196 (12)0.0165 (9)0.0136 (9)0.0041 (8)0.0026 (8)
O30.0208 (10)0.0135 (10)0.0161 (8)0.0038 (8)0.0004 (7)0.0033 (8)
O40.0485 (14)0.0232 (13)0.0149 (9)0.0146 (10)0.0013 (9)0.0001 (8)
O50.0261 (11)0.0199 (11)0.0151 (9)0.0089 (9)0.0005 (8)0.0013 (8)
O60.0321 (12)0.0325 (13)0.0149 (9)0.0118 (10)0.0028 (8)0.0008 (9)
O70.0189 (10)0.0124 (10)0.0134 (8)0.0010 (8)0.0034 (7)0.0002 (7)
N10.0293 (14)0.0211 (14)0.0145 (10)0.0064 (11)0.0029 (9)0.0008 (10)
N20.0253 (13)0.0208 (14)0.0153 (10)0.0041 (10)0.0033 (9)0.0010 (10)
N30.0333 (15)0.0228 (15)0.0177 (11)0.0048 (11)0.0004 (10)0.0040 (10)
N40.0225 (13)0.0299 (16)0.0279 (12)0.0017 (12)0.0032 (10)0.0023 (12)
N50.040 (2)0.057 (3)0.077 (2)0.0123 (18)0.0131 (17)0.0021 (19)
N60.0276 (16)0.054 (2)0.0332 (14)0.0128 (15)0.0060 (12)0.0020 (14)
C10.043 (2)0.0222 (18)0.0214 (13)0.0083 (14)0.0009 (13)0.0037 (13)
C20.0293 (17)0.0277 (18)0.0186 (13)0.0047 (14)0.0026 (11)0.0003 (12)
C30.053 (2)0.028 (2)0.0294 (16)0.0041 (17)0.0127 (15)0.0127 (15)
C40.0342 (19)0.031 (2)0.0328 (16)0.0087 (15)0.0059 (14)0.0063 (15)
C50.043 (2)0.071 (3)0.0389 (19)0.014 (2)0.0055 (17)0.002 (2)
C60.033 (2)0.096 (4)0.055 (2)0.006 (2)0.0132 (18)0.005 (3)
C70.028 (2)0.079 (4)0.052 (2)0.006 (2)0.0015 (16)0.004 (2)
C80.0253 (17)0.046 (2)0.0360 (17)0.0019 (16)0.0022 (13)0.0030 (17)
C90.0272 (17)0.035 (2)0.0310 (15)0.0025 (15)0.0032 (13)0.0079 (15)
C100.033 (2)0.065 (3)0.0405 (19)0.0214 (19)0.0033 (15)0.0014 (19)
C110.037 (2)0.036 (2)0.0428 (19)0.0040 (16)0.0138 (16)0.0023 (16)
C120.0230 (18)0.045 (3)0.063 (2)0.0047 (17)0.0151 (17)0.001 (2)
C130.0226 (14)0.0128 (14)0.0183 (12)0.0041 (11)0.0027 (10)0.0022 (11)
C140.0250 (15)0.0129 (14)0.0160 (11)0.0062 (11)0.0016 (10)0.0001 (11)
C150.0250 (15)0.0142 (15)0.0155 (12)0.0065 (12)0.0013 (10)0.0004 (11)
C160.0196 (14)0.0147 (14)0.0144 (11)0.0024 (11)0.0008 (10)0.0013 (10)
C170.0186 (14)0.0143 (14)0.0200 (12)0.0063 (11)0.0021 (10)0.0013 (11)
C180.0233 (15)0.0189 (16)0.0143 (11)0.0039 (12)0.0014 (10)0.0020 (11)
C190.0296 (16)0.0175 (15)0.0155 (12)0.0081 (12)0.0010 (11)0.0029 (11)
C200.0173 (13)0.0161 (14)0.0158 (12)0.0032 (11)0.0001 (10)0.0014 (11)
C210.0270 (15)0.0156 (15)0.0160 (12)0.0001 (12)0.0015 (10)0.0010 (11)
Geometric parameters (Å, º) top
Co1—O1i2.027 (2)C2—H20.9400
Co1—O3ii2.1926 (17)C3—H3A0.9800
Co1—O7i2.1230 (18)C3—H3B0.9800
Co1—O72.056 (2)C3—C41.508 (4)
Co1—N12.188 (2)C4—C51.384 (5)
Co1—N4iii2.163 (2)C4—C91.381 (4)
Co2—O22.058 (2)C5—H50.9400
Co2—O3iv2.2213 (18)C5—C61.370 (6)
Co2—O5v2.1241 (17)C6—H60.9400
Co2—O6v2.1770 (19)C6—C71.386 (5)
Co2—O72.0007 (18)C7—H7A0.9400
Co2—N22.127 (2)C7—C81.381 (5)
O1—C131.258 (3)C8—C91.391 (4)
O2—C131.254 (3)C8—C101.519 (5)
O3—C201.285 (3)C9—H90.9400
O4—C201.240 (3)C10—H10A0.9800
O5—C211.263 (3)C10—H10B0.9800
O6—C211.255 (3)C11—H110.9400
O7—H70.800 (17)C12—H120.9400
N1—N21.382 (3)C13—C141.504 (4)
N1—C11.301 (4)C14—C151.384 (3)
N2—C21.303 (3)C14—C191.390 (4)
N3—C11.348 (3)C15—H150.9400
N3—C21.353 (4)C15—C161.392 (4)
N3—C31.474 (4)C16—C171.390 (3)
N4—N51.382 (4)C16—C201.516 (4)
N4—C111.308 (4)C17—H170.9400
N5—C121.312 (5)C17—C181.394 (4)
N6—C101.465 (4)C18—C191.376 (4)
N6—C111.339 (4)C18—C211.502 (3)
N6—C121.333 (5)C19—H190.9400
C1—H10.9400
O1i—Co1—O3ii93.64 (8)N3—C2—H2124.6
O1i—Co1—O7i91.08 (8)N3—C3—H3A109.6
O1i—Co1—O7168.41 (9)N3—C3—H3B109.6
O1i—Co1—N184.29 (8)N3—C3—C4110.2 (3)
O1i—Co1—N4iii87.79 (10)H3A—C3—H3B108.1
O7i—Co1—O3ii80.63 (7)C4—C3—H3A109.6
O7—Co1—O3ii93.92 (7)C4—C3—H3B109.6
O7—Co1—O7i81.50 (8)C5—C4—C3119.8 (3)
O7i—Co1—N199.93 (8)C9—C4—C3120.8 (3)
O7—Co1—N188.21 (8)C9—C4—C5119.4 (3)
O7—Co1—N4iii100.25 (9)C4—C5—H5119.9
O7i—Co1—N4iii175.68 (8)C6—C5—C4120.1 (4)
N1—Co1—O3ii177.86 (8)C6—C5—H5119.9
N4iii—Co1—O3ii95.28 (8)C5—C6—H6119.9
N4iii—Co1—N184.12 (9)C5—C6—C7120.3 (4)
O2—Co2—O3iv91.68 (8)C7—C6—H6119.9
O2—Co2—O5v87.36 (8)C6—C7—H7A119.7
O2—Co2—O6v87.31 (8)C8—C7—C6120.5 (3)
O2—Co2—N2170.31 (9)C8—C7—H7A119.7
O5v—Co2—O3iv111.55 (7)C7—C8—C9118.6 (3)
O5v—Co2—O6v61.57 (7)C7—C8—C10123.4 (3)
O5v—Co2—N285.12 (8)C9—C8—C10118.0 (3)
O6v—Co2—O3iv173.08 (7)C4—C9—C8121.0 (3)
O7—Co2—O2100.21 (8)C4—C9—H9119.5
O7—Co2—O3iv82.64 (7)C8—C9—H9119.5
O7—Co2—O5v163.89 (8)N6—C10—C8113.8 (3)
O7—Co2—O6v104.28 (8)N6—C10—H10A108.8
O7—Co2—N288.60 (8)N6—C10—H10B108.8
N2—Co2—O3iv85.43 (8)C8—C10—H10A108.8
N2—Co2—O6v94.44 (9)C8—C10—H10B108.8
C13—O1—Co1i132.57 (18)H10A—C10—H10B107.7
C13—O2—Co2124.86 (17)N4—C11—N6110.6 (3)
Co1vi—O3—Co2vii88.24 (7)N4—C11—H11124.7
C20—O3—Co1vi116.93 (15)N6—C11—H11124.7
C20—O3—Co2vii139.95 (16)N5—C12—N6108.4 (3)
C21—O5—Co2viii89.32 (15)N5—C12—H12125.8
C21—O6—Co2viii87.17 (17)N6—C12—H12125.8
Co1—O7—Co1i98.50 (8)O1—C13—C14115.6 (2)
Co1i—O7—H7109 (2)O2—C13—O1125.5 (3)
Co1—O7—H7100 (2)O2—C13—C14118.9 (2)
Co2—O7—Co1i96.30 (8)C15—C14—C13122.5 (2)
Co2—O7—Co1121.07 (9)C15—C14—C19119.1 (3)
Co2—O7—H7128 (2)C19—C14—C13118.4 (2)
N2—N1—Co1115.26 (18)C14—C15—H15119.6
C1—N1—Co1131.7 (2)C14—C15—C16120.8 (2)
C1—N1—N2106.7 (2)C16—C15—H15119.6
N1—N2—Co2119.77 (16)C15—C16—C20118.1 (2)
C2—N2—Co2132.8 (2)C17—C16—C15119.2 (2)
C2—N2—N1106.9 (2)C17—C16—C20122.6 (2)
C1—N3—C2104.5 (2)C16—C17—H17120.0
C1—N3—C3129.2 (3)C16—C17—C18120.1 (3)
C2—N3—C3125.9 (2)C18—C17—H17120.0
N5—N4—Co1iii122.5 (2)C17—C18—C21121.6 (3)
C11—N4—Co1iii131.8 (2)C19—C18—C17119.8 (2)
C11—N4—N5105.3 (3)C19—C18—C21118.5 (2)
C12—N5—N4108.7 (3)C14—C19—H19119.6
C11—N6—C10128.3 (4)C18—C19—C14120.8 (2)
C12—N6—C10124.8 (3)C18—C19—H19119.6
C12—N6—C11106.9 (3)O3—C20—C16119.3 (2)
N1—C1—N3111.1 (3)O4—C20—O3123.9 (2)
N1—C1—H1124.5O4—C20—C16116.8 (3)
N3—C1—H1124.5O5—C21—C18118.9 (2)
N2—C2—N3110.7 (3)O6—C21—O5121.9 (2)
N2—C2—H2124.6O6—C21—C18119.2 (3)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x1/2, y+3/2, z+1/2; (iii) x, y+1, z+1; (iv) x+3/2, y1/2, z+3/2; (v) x1/2, y+3/2, z1/2; (vi) x+1/2, y+3/2, z1/2; (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···AD—HH···AD···AD—H···A
O7—H7···O4ii0.80 (2)2.08 (2)2.802 (3)149 (3)
C2—H2···O5iv0.942.453.194 (4)136
Symmetry codes: (ii) x1/2, y+3/2, z+1/2; (iv) x+3/2, y1/2, z+3/2.
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] (2) top
Crystal data top
[Cu4(C9H3O6)2(OH)2(C12H12N6)2(H2O)2]·H2OZ = 1
Mr = 1237.00F(000) = 626
Triclinic, P1Dx = 1.683 Mg m3
a = 10.9425 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.4580 (9) ÅCell parameters from 10482 reflections
c = 11.6193 (10) Åθ = 3.0–26.8°
α = 89.524 (7)°µ = 1.80 mm1
β = 69.945 (8)°T = 223 K
γ = 64.669 (8)°Block, blue
V = 1220.4 (2) Å30.50 × 0.20 × 0.10 mm
Data collection top
Agilent Gemini Atlas
diffractometer
4660 reflections with I > 2σ(I)
Detector resolution: 10.4471 pixels mm-1Rint = 0.041
MoKα scansθmax = 30.3°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 1515
Tmin = 0.472, Tmax = 0.827k = 1415
11737 measured reflectionsl = 1616
6238 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 1.30 e Å3
346 parametersΔρmin = 0.71 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cu10.60753 (5)0.05021 (4)0.00333 (4)0.01792 (13)
Cu20.29483 (5)0.28537 (4)0.16439 (4)0.02078 (14)
O10.6860 (3)0.0715 (3)0.1076 (2)0.0233 (6)
O20.6440 (4)0.0851 (3)0.2499 (3)0.0387 (8)
O30.6683 (4)0.0601 (3)0.6542 (2)0.0390 (8)
O40.7830 (3)0.2751 (3)0.6582 (2)0.0354 (8)
O51.1629 (3)0.5290 (3)0.2064 (3)0.0303 (7)
O61.0027 (4)0.5596 (3)0.1464 (3)0.0382 (8)
O70.4103 (3)0.0994 (3)0.1136 (2)0.0187 (5)
H70.400 (5)0.073 (4)0.187 (2)0.022*
O80.5001 (4)0.3075 (4)0.1694 (4)0.0556 (10)
H8A0.5473380.2569730.2077940.067*
H8B0.5540280.3284830.1160340.067*
N10.5135 (3)0.1945 (3)0.0847 (3)0.0204 (7)
N20.3755 (3)0.2917 (3)0.0186 (3)0.0205 (7)
N30.4306 (4)0.3096 (3)0.2141 (3)0.0222 (7)
N41.1890 (4)0.0015 (3)0.8890 (3)0.0233 (7)
N51.1257 (4)0.0674 (4)0.8157 (4)0.0437 (11)
N60.9609 (4)0.1350 (4)0.7871 (3)0.0281 (8)
C10.7546 (5)0.3061 (4)0.6113 (4)0.0277 (9)
C20.6266 (4)0.3024 (4)0.5362 (4)0.0237 (8)
H20.5850240.2615230.5697020.028*
C30.5601 (5)0.3591 (4)0.4117 (4)0.0262 (9)
C40.6209 (6)0.4198 (5)0.3640 (4)0.0402 (12)
H40.5743730.4605780.2805680.048*
C50.7499 (6)0.4217 (6)0.4375 (5)0.0481 (14)
H50.7917290.4619790.4036610.058*
C60.8171 (5)0.3636 (5)0.5616 (4)0.0373 (11)
H60.9052700.3634540.6116060.045*
C70.8186 (5)0.2542 (5)0.7485 (4)0.0318 (10)
H7A0.7496810.2340540.7696260.038*
H7B0.8316340.3224350.7951280.038*
C80.4206 (5)0.3545 (5)0.3322 (4)0.0287 (9)
H8C0.3380460.4416880.3143640.034*
H8D0.4037750.2944440.3772380.034*
C91.0874 (4)0.1225 (4)0.8691 (4)0.0260 (9)
H91.1018860.1906200.9073190.031*
C100.9877 (5)0.0154 (5)0.7547 (5)0.0444 (13)
H100.9183240.0055450.6973630.053*
C110.5431 (4)0.2069 (4)0.2022 (3)0.0228 (8)
H110.6300280.1518740.2680580.027*
C120.3276 (4)0.3605 (4)0.0985 (3)0.0228 (8)
H120.2361110.4335920.0783650.027*
C130.7562 (4)0.1363 (4)0.2755 (3)0.0191 (7)
C140.7230 (4)0.1096 (4)0.4022 (3)0.0224 (8)
H140.6567980.0246190.4459470.027*
C150.7866 (4)0.2071 (4)0.4649 (3)0.0220 (8)
C160.8902 (4)0.3312 (4)0.3995 (3)0.0228 (8)
H160.9362400.3963290.4411040.027*
C170.9260 (4)0.3592 (4)0.2718 (3)0.0207 (8)
C180.8574 (4)0.2623 (4)0.2110 (3)0.0191 (8)
H180.8793220.2817380.1257470.023*
C190.6892 (4)0.0309 (4)0.2074 (3)0.0215 (8)
C200.7431 (5)0.1763 (4)0.6041 (3)0.0266 (9)
C211.0368 (4)0.4936 (4)0.2022 (3)0.0216 (8)
O91.2981 (11)0.3602 (8)0.9392 (8)0.072 (3)0.5
H9A1.2490260.4139170.8908570.087*0.5
H9B1.2366260.2600170.8982560.087*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0169 (2)0.0165 (2)0.0141 (2)0.00314 (18)0.00457 (18)0.00179 (16)
Cu20.0211 (3)0.0157 (2)0.0132 (2)0.00198 (18)0.00560 (19)0.00255 (17)
O10.0231 (14)0.0207 (14)0.0181 (12)0.0018 (11)0.0089 (11)0.0029 (10)
O20.058 (2)0.0181 (16)0.0437 (18)0.0087 (15)0.0337 (17)0.0049 (13)
O30.058 (2)0.0227 (16)0.0162 (13)0.0050 (15)0.0084 (14)0.0019 (11)
O40.0411 (18)0.0254 (16)0.0128 (12)0.0054 (13)0.0061 (13)0.0014 (11)
O50.0260 (15)0.0198 (15)0.0301 (15)0.0042 (12)0.0122 (13)0.0070 (12)
O60.0367 (18)0.0263 (17)0.0409 (17)0.0077 (14)0.0105 (15)0.0084 (14)
O70.0222 (13)0.0165 (13)0.0103 (11)0.0040 (11)0.0043 (10)0.0003 (9)
O80.061 (2)0.036 (2)0.087 (3)0.0160 (19)0.056 (2)0.0111 (19)
N10.0209 (16)0.0146 (15)0.0205 (15)0.0055 (13)0.0054 (13)0.0021 (12)
N20.0186 (16)0.0144 (15)0.0182 (15)0.0011 (12)0.0033 (13)0.0010 (12)
N30.0209 (16)0.0207 (17)0.0160 (14)0.0047 (13)0.0028 (13)0.0051 (12)
N40.0203 (16)0.0204 (17)0.0263 (16)0.0092 (14)0.0054 (14)0.0037 (13)
N50.034 (2)0.033 (2)0.055 (3)0.0160 (19)0.006 (2)0.0118 (19)
N60.0195 (17)0.0279 (19)0.0292 (18)0.0078 (15)0.0044 (15)0.0034 (14)
C10.026 (2)0.023 (2)0.026 (2)0.0066 (17)0.0070 (17)0.0046 (16)
C20.023 (2)0.0192 (19)0.0245 (19)0.0048 (16)0.0100 (16)0.0041 (15)
C30.027 (2)0.022 (2)0.0223 (18)0.0064 (17)0.0075 (17)0.0073 (15)
C40.052 (3)0.045 (3)0.027 (2)0.028 (3)0.010 (2)0.000 (2)
C50.057 (3)0.062 (4)0.041 (3)0.043 (3)0.015 (3)0.005 (2)
C60.030 (2)0.050 (3)0.034 (2)0.023 (2)0.008 (2)0.010 (2)
C70.020 (2)0.036 (3)0.026 (2)0.0052 (18)0.0043 (17)0.0025 (18)
C80.026 (2)0.037 (2)0.0210 (19)0.0114 (19)0.0098 (17)0.0120 (17)
C90.0184 (19)0.026 (2)0.0232 (19)0.0057 (16)0.0020 (16)0.0032 (16)
C100.028 (2)0.034 (3)0.057 (3)0.013 (2)0.001 (2)0.017 (2)
C110.0227 (19)0.0168 (18)0.0184 (17)0.0035 (15)0.0027 (16)0.0036 (14)
C120.0216 (19)0.0203 (19)0.0198 (17)0.0033 (16)0.0082 (16)0.0043 (14)
C130.0195 (18)0.0173 (18)0.0182 (17)0.0066 (15)0.0064 (15)0.0022 (14)
C140.0206 (19)0.0196 (19)0.0172 (17)0.0031 (15)0.0034 (15)0.0021 (14)
C150.0206 (19)0.024 (2)0.0142 (16)0.0054 (16)0.0046 (15)0.0003 (14)
C160.025 (2)0.0200 (19)0.0164 (17)0.0036 (16)0.0078 (16)0.0020 (14)
C170.0169 (18)0.0202 (19)0.0154 (16)0.0019 (15)0.0036 (14)0.0005 (14)
C180.0188 (18)0.0197 (18)0.0123 (15)0.0044 (15)0.0039 (14)0.0000 (13)
C190.0193 (18)0.0209 (19)0.0209 (17)0.0063 (15)0.0073 (15)0.0051 (14)
C200.026 (2)0.028 (2)0.0155 (17)0.0031 (17)0.0067 (16)0.0003 (15)
C210.024 (2)0.0167 (18)0.0131 (16)0.0021 (15)0.0040 (15)0.0029 (13)
O90.112 (7)0.059 (5)0.063 (5)0.075 (6)0.005 (5)0.002 (4)
Geometric parameters (Å, º) top
Cu1—Cu1i3.0515 (10)C1—C61.377 (7)
Cu1—O11.952 (3)C1—C71.509 (6)
Cu1—O7i2.308 (3)C2—H20.9400
Cu1—O71.921 (3)C2—C31.390 (5)
Cu1—N12.019 (3)C3—C41.374 (7)
Cu1—N4ii1.982 (3)C3—C81.512 (6)
Cu2—O4iii1.966 (3)C4—H40.9400
Cu2—O5iv1.937 (3)C4—C51.387 (7)
Cu2—O71.921 (3)C5—H50.9400
Cu2—O82.385 (4)C5—C61.390 (7)
Cu2—N22.018 (3)C6—H60.9400
O1—C191.271 (5)C7—H7A0.9800
O2—C191.240 (5)C7—H7B0.9800
O3—C201.239 (5)C8—H8C0.9800
O4—C201.273 (5)C8—H8D0.9800
O5—C211.280 (5)C9—H90.9400
O6—C211.244 (5)C10—H100.9400
O7—H70.891 (10)C11—H110.9400
O8—H8A0.8369C12—H120.9400
O8—H8B0.8113C13—C141.392 (5)
N1—N21.375 (4)C13—C181.398 (5)
N1—C111.312 (5)C13—C191.498 (5)
N2—C121.313 (5)C14—H140.9400
N3—C81.484 (5)C14—C151.389 (6)
N3—C111.340 (5)C15—C161.390 (5)
N3—C121.352 (5)C15—C201.518 (5)
N4—N51.371 (5)C16—H160.9400
N4—C91.312 (5)C16—C171.400 (5)
N5—C101.317 (6)C17—C181.390 (5)
N6—C71.484 (5)C17—C211.499 (5)
N6—C91.331 (5)C18—H180.9400
N6—C101.353 (6)O9—H9A1.0263
C1—C21.393 (6)O9—H9B1.0606
O1—Cu1—Cu1i95.19 (9)C3—C4—H4119.6
O1—Cu1—O7i95.32 (11)C3—C4—C5120.8 (4)
O1—Cu1—N1172.47 (12)C5—C4—H4119.6
O1—Cu1—N4ii88.15 (13)C4—C5—H5120.3
O7—Cu1—Cu1i49.12 (8)C4—C5—C6119.5 (5)
O7i—Cu1—Cu1i39.00 (6)C6—C5—H5120.3
O7—Cu1—O191.85 (11)C1—C6—C5120.1 (4)
O7—Cu1—O7i88.11 (9)C1—C6—H6119.9
O7—Cu1—N184.31 (12)C5—C6—H6119.9
O7—Cu1—N4ii179.60 (13)N6—C7—C1113.0 (4)
N1—Cu1—Cu1i87.20 (9)N6—C7—H7A109.0
N1—Cu1—O7i91.03 (11)N6—C7—H7B109.0
N4ii—Cu1—Cu1i130.49 (10)C1—C7—H7A109.0
N4ii—Cu1—O7i91.49 (12)C1—C7—H7B109.0
N4ii—Cu1—N195.74 (13)H7A—C7—H7B107.8
O4iii—Cu2—O895.54 (15)N3—C8—C3110.1 (3)
O4iii—Cu2—N2178.71 (13)N3—C8—H8C109.6
O5iv—Cu2—O4iii87.65 (12)N3—C8—H8D109.6
O5iv—Cu2—O895.44 (13)C3—C8—H8C109.6
O5iv—Cu2—N293.46 (13)C3—C8—H8D109.6
O7—Cu2—O4iii94.57 (11)H8C—C8—H8D108.2
O7—Cu2—O5iv172.97 (12)N4—C9—N6110.4 (4)
O7—Cu2—O890.99 (12)N4—C9—H9124.8
O7—Cu2—N284.25 (11)N6—C9—H9124.8
N2—Cu2—O885.00 (14)N5—C10—N6109.7 (4)
C19—O1—Cu1121.2 (3)N5—C10—H10125.2
C20—O4—Cu2iii128.3 (2)N6—C10—H10125.2
C21—O5—Cu2v116.8 (3)N1—C11—N3109.7 (3)
Cu1—O7—Cu1i91.89 (9)N1—C11—H11125.1
Cu1i—O7—H7105 (3)N3—C11—H11125.1
Cu1—O7—H7116 (3)N2—C12—N3109.3 (3)
Cu2—O7—Cu1113.05 (13)N2—C12—H12125.4
Cu2—O7—Cu1i131.57 (14)N3—C12—H12125.4
Cu2—O7—H7101 (3)C14—C13—C18119.0 (4)
Cu2—O8—H8A116.6C14—C13—C19120.9 (3)
Cu2—O8—H8B127.6C18—C13—C19120.0 (3)
H8A—O8—H8B108.8C13—C14—H14119.6
N2—N1—Cu1118.2 (2)C15—C14—C13120.8 (3)
C11—N1—Cu1133.2 (3)C15—C14—H14119.6
C11—N1—N2107.2 (3)C14—C15—C16119.8 (3)
N1—N2—Cu2115.5 (2)C14—C15—C20119.5 (3)
C12—N2—Cu2136.9 (3)C16—C15—C20120.7 (4)
C12—N2—N1107.3 (3)C15—C16—H16120.0
C11—N3—C8126.2 (3)C15—C16—C17120.0 (4)
C11—N3—C12106.4 (3)C17—C16—H16120.0
C12—N3—C8127.3 (3)C16—C17—C21119.7 (3)
N5—N4—Cu1ii131.8 (3)C18—C17—C16119.6 (3)
C9—N4—Cu1ii120.9 (3)C18—C17—C21120.6 (3)
C9—N4—N5107.3 (3)C13—C18—H18119.7
C10—N5—N4106.9 (4)C17—C18—C13120.6 (3)
C9—N6—C7126.1 (4)C17—C18—H18119.7
C9—N6—C10105.9 (4)O1—C19—C13115.0 (3)
C10—N6—C7127.9 (4)O2—C19—O1125.7 (4)
C2—C1—C7119.4 (4)O2—C19—C13119.4 (4)
C6—C1—C2120.0 (4)O3—C20—O4126.6 (4)
C6—C1—C7120.6 (4)O3—C20—C15117.8 (4)
C1—C2—H2120.0O4—C20—C15115.5 (3)
C3—C2—C1120.0 (4)O5—C21—C17113.9 (4)
C3—C2—H2120.0O6—C21—O5125.9 (4)
C2—C3—C8119.0 (4)O6—C21—C17120.2 (4)
C4—C3—C2119.5 (4)H9A—O9—H9B110.4
C4—C3—C8121.4 (4)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z1; (iii) x+1, y, z+1; (iv) x1, y+1, z; (v) x+1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O3iii0.89 (1)1.77 (2)2.635 (4)164 (4)
O8—H8A···O20.841.952.718 (5)153
O8—H8B···O9ii0.812.283.075 (8)168
O9—H9A···O5vi1.032.053.078 (7)177
O9—H9B···N51.062.053.112 (9)177
Symmetry codes: (ii) x+2, y, z1; (iii) x+1, y, z+1; (vi) x, y, z1.
 

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