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The reaction of Cu(NO3)2·3H2O with 2,4′-oxybis(benzoic acid) and 4,4′-bi­­pyridine under hydro­thermal conditions produced a new mixed-ligand two-dimensional copper(II) coordination polymer, namely poly[[(μ-4,4′-bi­pyridine-κ2N,N′)[μ-2,4′-oxybis(benzoato)-κ4O2,O2′:O4,O4′]copper(II)] monohydrate], {[Cu(C14H8O5)(C10H8N2)]·H2O}n, which was characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis and single-crystal X-ray diffraction. The X-ray diffraction crystal structure analysis reveals that the CuII ions are connected to form a two-dimensional wave-like network through 4,4′-bi­pyridine and 2,4′-oxybis(benzoate) ligands. The two-dimensional layers are expanded into a three-dimensional supra­molecular structure through inter­molecular O—H...O and C—H...O hydrogen bonds. Furthermore, magnetic susceptibility measurements indicate that the complex shows weak anti­ferromagnetic inter­actions between adjacent CuII ions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617007537/ov3089sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617007537/ov3089Isup2.hkl
Contains datablock I

CCDC reference: 1534325

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

Poly[[(µ-4,4'-bipyridine-κ2N,N')(µ-2,4'-oxydibenzoato-κ4O2,O2':O4,O4')copper(II)] monohydrate]{[Cu(C14H8O5)(C10H8N2)]·H2O top
Crystal data top
[Cu(C14H8O5)(C10H8N2)]·H2OF(000) = 1012
Mr = 493.94Dx = 1.510 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.731 (4) ÅCell parameters from 2152 reflections
b = 14.274 (5) Åθ = 2.3–23.7°
c = 13.211 (5) ŵ = 1.05 mm1
β = 100.862 (7)°T = 296 K
V = 2172.6 (14) Å3Block, blue
Z = 40.34 × 0.25 × 0.21 mm
Data collection top
Bruker SMART
diffractometer
2612 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 139
Tmin = 0.737, Tmax = 0.802k = 1614
10779 measured reflectionsl = 1415
3821 independent reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0572P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3821 reflectionsΔρmax = 0.50 e Å3
302 parametersΔρmin = 0.33 e Å3
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)
Cu10.16833 (3)0.25361 (3)0.81160 (3)0.03615 (15)
O10.2541 (2)0.36943 (15)0.85492 (19)0.0445 (6)
O20.3035 (3)0.3459 (2)0.7048 (2)0.0777 (9)
O30.52529 (19)0.41323 (16)0.89850 (19)0.0487 (6)
O41.01783 (19)0.32147 (16)0.78438 (19)0.0464 (6)
O51.0173 (2)0.22406 (17)0.91366 (19)0.0492 (6)
N10.2914 (2)0.16870 (18)0.8878 (2)0.0389 (7)
N20.1073 (2)0.15638 (17)0.7053 (2)0.0347 (6)
C10.3033 (3)0.3943 (2)0.7809 (3)0.0402 (8)
C20.3640 (3)0.4872 (2)0.7944 (3)0.0368 (8)
C30.3108 (3)0.5690 (2)0.7508 (3)0.0526 (10)
H30.23690.56610.71030.063*
C40.3677 (4)0.6545 (3)0.7675 (3)0.0630 (12)
H40.33150.70870.73830.076*
C50.4771 (4)0.6597 (3)0.8270 (4)0.0626 (12)
H50.51440.71730.83780.075*
C60.5317 (3)0.5800 (3)0.8707 (3)0.0528 (10)
H6A0.60530.58350.91160.063*
C70.4754 (3)0.4951 (2)0.8528 (3)0.0381 (8)
C80.6353 (3)0.3882 (2)0.8843 (3)0.0381 (8)
C90.6796 (3)0.4123 (2)0.7986 (3)0.0416 (9)
H90.63690.44990.74770.050*
C100.7885 (3)0.3800 (2)0.7890 (3)0.0405 (8)
H100.81950.39750.73200.049*
C110.8520 (3)0.3221 (2)0.8632 (3)0.0371 (8)
C120.8054 (3)0.2985 (3)0.9479 (3)0.0456 (9)
H120.84710.25950.99800.055*
C130.6971 (3)0.3318 (3)0.9603 (3)0.0469 (9)
H130.66710.31631.01840.056*
C140.9689 (3)0.2868 (2)0.8542 (3)0.0406 (9)
C150.2607 (3)0.0891 (3)0.9274 (3)0.0595 (11)
H150.18210.07810.92520.071*
C160.3387 (3)0.0220 (3)0.9715 (3)0.0574 (11)
H160.31210.03280.99720.069*
C170.4563 (3)0.0358 (2)0.9778 (2)0.0366 (8)
C180.4870 (3)0.1191 (3)0.9397 (4)0.0705 (13)
H180.56520.13290.94360.085*
C190.4047 (3)0.1832 (3)0.8958 (4)0.0669 (13)
H190.42930.23900.87060.080*
C200.1584 (3)0.1482 (2)0.6235 (3)0.0406 (8)
H200.22280.18530.62080.049*
C210.1203 (3)0.0871 (2)0.5423 (2)0.0385 (8)
H210.15980.08290.48770.046*
C220.0233 (3)0.0324 (2)0.5434 (2)0.0314 (7)
C230.0299 (3)0.0406 (2)0.6283 (3)0.0442 (9)
H230.09540.00520.63250.053*
C240.0153 (3)0.1019 (2)0.7067 (3)0.0467 (9)
H240.02060.10540.76360.056*
O60.9603 (5)0.4138 (4)0.5754 (4)0.1208 (19)0.703 (5)
H6B0.97700.38820.63450.181*0.703 (5)
H6C0.97650.37610.53040.181*0.703 (5)
O6B0.9064 (12)0.4388 (9)0.4695 (10)0.1208 (19)0.297 (5)
H6D0.94280.40370.42230.181*0.297 (5)
H6E0.92110.50440.46220.181*0.297 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0265 (2)0.0303 (2)0.0510 (3)0.00179 (19)0.00559 (17)0.00342 (19)
O10.0376 (14)0.0380 (13)0.0618 (16)0.0068 (12)0.0191 (12)0.0064 (11)
O20.118 (3)0.0579 (18)0.0629 (19)0.0229 (18)0.0322 (18)0.0125 (15)
O30.0262 (13)0.0493 (14)0.0734 (17)0.0087 (12)0.0162 (12)0.0208 (13)
O40.0310 (14)0.0374 (13)0.0730 (17)0.0042 (12)0.0153 (13)0.0008 (12)
O50.0353 (14)0.0513 (15)0.0606 (16)0.0115 (13)0.0076 (12)0.0034 (12)
N10.0316 (16)0.0347 (15)0.0502 (17)0.0009 (14)0.0072 (13)0.0031 (13)
N20.0268 (15)0.0325 (15)0.0453 (16)0.0022 (13)0.0077 (13)0.0022 (12)
C10.033 (2)0.0349 (19)0.052 (2)0.0017 (16)0.0061 (18)0.0000 (17)
C20.0317 (19)0.0321 (18)0.050 (2)0.0047 (16)0.0156 (16)0.0053 (15)
C30.036 (2)0.047 (2)0.075 (3)0.0111 (19)0.011 (2)0.014 (2)
C40.058 (3)0.035 (2)0.100 (3)0.008 (2)0.027 (3)0.019 (2)
C50.057 (3)0.033 (2)0.104 (3)0.012 (2)0.034 (3)0.005 (2)
C60.036 (2)0.052 (2)0.073 (3)0.007 (2)0.0175 (19)0.001 (2)
C70.030 (2)0.0299 (18)0.057 (2)0.0032 (16)0.0159 (17)0.0076 (16)
C80.0212 (18)0.0358 (19)0.057 (2)0.0013 (15)0.0057 (16)0.0000 (16)
C90.032 (2)0.0395 (19)0.053 (2)0.0026 (17)0.0068 (17)0.0071 (17)
C100.034 (2)0.0352 (19)0.055 (2)0.0027 (17)0.0145 (17)0.0002 (16)
C110.0235 (18)0.0328 (18)0.054 (2)0.0038 (15)0.0056 (16)0.0121 (16)
C120.031 (2)0.050 (2)0.051 (2)0.0082 (18)0.0027 (17)0.0031 (17)
C130.034 (2)0.055 (2)0.052 (2)0.0038 (19)0.0084 (17)0.0086 (18)
C140.029 (2)0.0338 (18)0.056 (2)0.0012 (17)0.0000 (18)0.0129 (17)
C150.026 (2)0.064 (3)0.088 (3)0.005 (2)0.011 (2)0.030 (2)
C160.036 (2)0.049 (2)0.088 (3)0.0004 (19)0.013 (2)0.032 (2)
C170.032 (2)0.0370 (19)0.0395 (19)0.0031 (16)0.0048 (15)0.0029 (14)
C180.027 (2)0.060 (3)0.123 (4)0.004 (2)0.012 (2)0.034 (3)
C190.028 (2)0.049 (2)0.123 (4)0.001 (2)0.013 (2)0.030 (2)
C200.0291 (19)0.0398 (19)0.051 (2)0.0059 (16)0.0038 (17)0.0004 (16)
C210.0325 (19)0.044 (2)0.0398 (19)0.0042 (17)0.0093 (15)0.0010 (16)
C220.0296 (18)0.0255 (16)0.0378 (19)0.0064 (14)0.0034 (15)0.0051 (13)
C230.041 (2)0.037 (2)0.057 (2)0.0132 (17)0.0156 (18)0.0093 (16)
C240.050 (2)0.041 (2)0.054 (2)0.0069 (19)0.0228 (19)0.0104 (17)
O60.141 (5)0.111 (4)0.116 (4)0.022 (4)0.040 (4)0.011 (3)
O6B0.141 (5)0.111 (4)0.116 (4)0.022 (4)0.040 (4)0.011 (3)
Geometric parameters (Å, º) top
Cu1—O11.964 (2)C9—H90.9300
Cu1—O4i1.986 (2)C10—C111.387 (4)
Cu1—N12.004 (3)C10—H100.9300
Cu1—N22.008 (3)C11—C121.376 (5)
Cu1—O22.661 (3)C11—C141.487 (5)
Cu1—O5i2.457 (3)C12—C131.395 (5)
O1—C11.275 (4)C12—H120.9300
O2—C11.221 (4)C13—H130.9300
O3—C81.386 (4)C15—C161.375 (5)
O3—C71.393 (4)C15—H150.9300
O4—C141.275 (4)C16—C171.381 (5)
O4—Cu1ii1.986 (2)C16—H160.9300
O5—C141.254 (4)C17—C181.365 (5)
N1—C151.329 (4)C17—C17iii1.488 (6)
N1—C191.330 (4)C18—C191.377 (5)
N2—C241.333 (4)C18—H180.9300
N2—C201.335 (4)C19—H190.9300
C1—C21.500 (4)C20—C211.390 (4)
C2—C71.391 (5)C20—H200.9300
C2—C31.396 (4)C21—C221.382 (4)
C3—C41.390 (5)C21—H210.9300
C3—H30.9300C22—C231.388 (5)
C4—C51.374 (5)C22—C22iv1.494 (6)
C4—H40.9300C23—C241.383 (4)
C5—C61.377 (5)C23—H230.9300
C5—H50.9300C24—H240.9300
C6—C71.379 (5)O6—H6B0.8503
C6—H6A0.9300O6—H6C0.8498
C8—C91.375 (5)O6B—H6D0.9600
C8—C131.381 (4)O6B—H6E0.9600
C9—C101.387 (5)
O1—Cu1—O4i91.80 (10)C8—C9—H9120.4
O1—Cu1—N194.69 (11)C10—C9—H9120.4
O4i—Cu1—N1156.51 (11)C9—C10—C11121.0 (3)
O1—Cu1—N2151.80 (11)C9—C10—H10119.5
O4i—Cu1—N291.30 (10)C11—C10—H10119.5
N1—Cu1—N293.52 (11)C12—C11—C10118.6 (3)
O2—Cu1—N196.94 (10)C12—C11—C14119.7 (3)
O2—Cu1—N298.10 (10)C10—C11—C14121.7 (3)
O2—Cu1—O154.13 (10)C11—C12—C13121.5 (3)
O2—Cu1—O4i105.11 (10)C11—C12—H12119.3
O2—Cu1—O5i159.93 (9)C13—C12—H12119.3
O1—Cu1—O5i111.56 (9)C8—C13—C12118.5 (3)
N1—Cu1—O5i98.41 (9)C8—C13—H13120.7
N2—Cu1—O5i93.80 (9)C12—C13—H13120.7
O4i—Cu1—O5i58.31 (9)O5—C14—O4121.2 (3)
C1—O1—Cu1107.0 (2)O5—C14—C11120.5 (4)
C8—O3—C7118.9 (3)O4—C14—C11118.3 (3)
C14—O4—Cu1ii100.7 (2)N1—C15—C16123.7 (3)
C15—N1—C19116.3 (3)N1—C15—H15118.2
C15—N1—Cu1119.5 (2)C16—C15—H15118.2
C19—N1—Cu1124.1 (2)C15—C16—C17120.2 (3)
C24—N2—C20116.6 (3)C15—C16—H16119.9
C24—N2—Cu1125.2 (2)C17—C16—H16119.9
C20—N2—Cu1118.1 (2)C18—C17—C16115.6 (3)
O2—C1—O1123.1 (3)C18—C17—C17iii122.3 (4)
O2—C1—C2121.5 (3)C16—C17—C17iii122.1 (4)
O1—C1—C2115.4 (3)C17—C18—C19121.4 (4)
C7—C2—C3117.4 (3)C17—C18—H18119.3
C7—C2—C1120.9 (3)C19—C18—H18119.3
C3—C2—C1121.7 (3)N1—C19—C18122.8 (4)
C4—C3—C2120.4 (4)N1—C19—H19118.6
C4—C3—H3119.8C18—C19—H19118.6
C2—C3—H3119.8N2—C20—C21123.5 (3)
C5—C4—C3120.4 (4)N2—C20—H20118.3
C5—C4—H4119.8C21—C20—H20118.3
C3—C4—H4119.8C22—C21—C20119.5 (3)
C4—C5—C6120.4 (4)C22—C21—H21120.3
C4—C5—H5119.8C20—C21—H21120.3
C6—C5—H5119.8C21—C22—C23117.2 (3)
C5—C6—C7118.9 (4)C21—C22—C22iv121.6 (4)
C5—C6—H6A120.5C23—C22—C22iv121.2 (4)
C7—C6—H6A120.5C24—C23—C22119.4 (3)
C6—C7—C2122.4 (3)C24—C23—H23120.3
C6—C7—O3121.0 (3)C22—C23—H23120.3
C2—C7—O3116.5 (3)N2—C24—C23123.8 (3)
C9—C8—C13121.1 (3)N2—C24—H24118.1
C9—C8—O3123.5 (3)C23—C24—H24118.1
C13—C8—O3115.2 (3)H6B—O6—H6C109.1
C8—C9—C10119.3 (3)H6D—O6B—H6E109.5
Cu1—O1—C1—O27.2 (4)O3—C8—C13—C12175.8 (3)
Cu1—O1—C1—C2174.1 (2)C11—C12—C13—C81.2 (5)
O2—C1—C2—C796.8 (4)Cu1ii—O4—C14—O52.4 (4)
O1—C1—C2—C781.9 (4)Cu1ii—O4—C14—C11178.0 (2)
O2—C1—C2—C384.4 (5)C12—C11—C14—O511.5 (5)
O1—C1—C2—C396.9 (4)C10—C11—C14—O5169.5 (3)
C7—C2—C3—C41.1 (5)C12—C11—C14—O4168.8 (3)
C1—C2—C3—C4177.8 (4)C10—C11—C14—O410.1 (5)
C2—C3—C4—C50.1 (6)C19—N1—C15—C162.3 (6)
C3—C4—C5—C60.1 (7)Cu1—N1—C15—C16173.1 (3)
C4—C5—C6—C70.7 (6)N1—C15—C16—C170.8 (7)
C5—C6—C7—C21.8 (6)C15—C16—C17—C181.2 (6)
C5—C6—C7—O3177.5 (3)C15—C16—C17—C17iii178.3 (4)
C3—C2—C7—C61.9 (5)C16—C17—C18—C191.7 (6)
C1—C2—C7—C6176.9 (3)C17iii—C17—C18—C19177.8 (4)
C3—C2—C7—O3177.9 (3)C15—N1—C19—C181.7 (6)
C1—C2—C7—O31.0 (5)Cu1—N1—C19—C18173.4 (4)
C8—O3—C7—C655.3 (5)C17—C18—C19—N10.2 (8)
C8—O3—C7—C2128.7 (3)C24—N2—C20—C210.1 (5)
C7—O3—C8—C928.5 (5)Cu1—N2—C20—C21176.5 (2)
C7—O3—C8—C13155.1 (3)N2—C20—C21—C221.3 (5)
C13—C8—C9—C100.6 (5)C20—C21—C22—C231.3 (5)
O3—C8—C9—C10176.8 (3)C20—C21—C22—C22iv178.2 (3)
C8—C9—C10—C111.5 (5)C21—C22—C23—C240.1 (5)
C9—C10—C11—C121.1 (5)C22iv—C22—C23—C24179.5 (3)
C9—C10—C11—C14179.9 (3)C20—N2—C24—C231.5 (5)
C10—C11—C12—C130.2 (5)Cu1—N2—C24—C23174.9 (3)
C14—C11—C12—C13178.7 (3)C22—C23—C24—N21.4 (6)
C9—C8—C13—C120.7 (5)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z+2; (iv) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6B—H6E···O6Bv0.962.212.80 (3)119
O6B—H6D···O5vi0.962.042.829 (13)139
O6—H6B···O40.852.173.019 (6)179
O6—H6C···O5vi0.852.223.070 (6)179
C24—H24···O5i0.932.583.239 (4)128
C21—H21···O1vi0.932.343.232 (4)160
C20—H20···O20.932.643.365 (4)135
O6B—H6E···O6Bv0.962.212.80 (3)119
O6B—H6D···O5vi0.962.042.829 (13)139
O6—H6C···O5vi0.852.223.070 (6)179
O6—H6B···O40.852.173.019 (6)179
C24—H24···O5i0.932.583.239 (4)128
C21—H21···O1vi0.932.343.232 (4)160
C20—H20···O20.932.643.365 (4)135
O6B—H6E···O6Bv0.962.212.80 (3)119
O6B—H6D···O5vi0.962.042.829 (13)139
O6—H6C···O5vi0.852.223.070 (6)179
O6—H6B···O40.852.173.019 (6)179
C24—H24···O5i0.932.583.239 (4)128
C21—H21···O1vi0.932.343.232 (4)160
C20—H20···O20.932.643.365 (4)135
C20—H20···O20.932.643.365 (4)135
C21—H21···O1vi0.932.343.232 (4)160
C24—H24···O5i0.932.583.239 (4)128
O6—H6B···O40.852.173.019 (6)179
O6—H6C···O5vi0.852.223.070 (6)179
O6B—H6D···O5vi0.962.042.829 (13)139
O6B—H6E···O6Bv0.962.212.80 (3)119
C20—H20···O20.932.643.365 (4)135
C21—H21···O1vi0.932.343.232 (4)160
C24—H24···O5i0.932.583.239 (4)128
O6—H6B···O40.852.173.019 (6)179
O6—H6C···O5vi0.852.223.070 (6)179
O6B—H6D···O5vi0.962.042.829 (13)139
O6B—H6E···O6Bv0.962.212.80 (3)119
C20—H20···O20.932.643.365 (4)135
C21—H21···O1vi0.932.343.232 (4)160
C24—H24···O5i0.932.583.239 (4)128
O6—H6B···O40.852.173.019 (6)179
O6—H6C···O5vi0.852.223.070 (6)179
O6B—H6D···O5vi0.962.042.829 (13)139
O6B—H6E···O6Bv0.962.212.80 (3)119
Symmetry codes: (i) x1, y, z; (v) x+2, y+1, z+1; (vi) x, y+1/2, z1/2.
 

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