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In the title compound, [Zn2(C6H8O4)2(C12H8N2)2(H2O)2], each Zn atom is six-coordinated in the ZnO4N2 form in a distorted tetragonal–bipyramidal geometry. The water molecules act as donors in O—H...O hydrogen bonds, connecting the molecules into chains. The packing is further stabilized by intermolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680403288X/cv6431sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680403288X/cv6431Isup2.hkl
Contains datablock I

CCDC reference: 262271

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Some non-H atoms missing
  • R factor = 0.024
  • wR factor = 0.065
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O3 .. 30.48 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O4 .. 10.94 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N2 .. 6.17 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

di-µ-adipato-κ6O,O':O'';O:O',O''-bis[aqua(1,10-phenanthroline- κ2N,N')zinc(II)] top
Crystal data top
[Zn2(C6H8O4)2(C12H8N2)2(H2O)2]Z = 1
Mr = 407.71F(000) = 420
Triclinic, P1Dx = 1.609 Mg m3
a = 8.1984 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7549 (5) ÅCell parameters from 3889 reflections
c = 11.8636 (6) Åθ = 2.3–26.0°
α = 70.971 (1)°µ = 1.49 mm1
β = 75.508 (1)°T = 293 K
γ = 72.077 (1)°Plate, pink
V = 841.48 (7) Å30.54 × 0.15 × 0.08 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3228 independent reflections
Radiation source: fine-focus sealed tube3094 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1012
Tmin = 0.500, Tmax = 0.890l = 1413
4743 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0373P)2 + 0.2537P]
where P = (Fo2 + 2Fc2)/3
3228 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.06374 (2)0.14741 (2)0.291440 (15)0.03325 (8)
O1W0.07073 (18)0.01149 (15)0.38210 (11)0.0366 (3)
O40.26164 (16)0.08574 (15)0.39055 (11)0.0408 (3)
O10.1033 (2)0.31354 (17)0.35850 (14)0.0563 (4)
O30.3049 (2)0.26808 (15)0.22882 (12)0.0522 (3)
N20.02543 (19)0.25473 (16)0.12310 (13)0.0355 (3)
N10.22272 (18)0.00009 (16)0.17503 (12)0.0350 (3)
C110.0567 (2)0.18910 (19)0.03249 (14)0.0342 (3)
C160.3447 (2)0.18388 (18)0.32699 (15)0.0336 (3)
O20.1077 (2)0.28558 (16)0.55299 (13)0.0629 (4)
C120.1889 (2)0.05181 (19)0.06083 (14)0.0335 (3)
C70.0164 (3)0.2490 (2)0.08530 (15)0.0435 (4)
C170.4907 (2)0.1959 (2)0.37621 (17)0.0390 (4)
H17A0.55750.25910.31320.047*
H17B0.56760.09730.40020.047*
C130.1442 (2)0.35907 (19)0.45197 (16)0.0376 (4)
C40.2760 (2)0.0217 (2)0.02960 (16)0.0423 (4)
C140.2486 (3)0.5204 (2)0.43380 (17)0.0454 (4)
H14B0.17900.58310.37290.055*
H14A0.35080.53130.40140.055*
C180.4225 (2)0.2612 (2)0.48479 (17)0.0397 (4)
H18A0.35660.19690.54750.060*
H18B0.52070.26070.51670.060*
C150.3078 (2)0.58025 (19)0.54365 (16)0.0395 (4)
H15A0.20690.57940.57280.059*
H15B0.37190.51550.60740.059*
C10.3435 (2)0.1258 (2)0.20292 (17)0.0434 (4)
H10.36660.16250.28170.052*
C100.1483 (3)0.3810 (2)0.09853 (18)0.0469 (4)
H100.20620.42630.16030.056*
C60.1056 (3)0.1687 (3)0.17407 (17)0.0533 (5)
H60.07780.20620.25160.064*
C50.2281 (3)0.0410 (3)0.14757 (17)0.0541 (5)
H50.28360.00840.20720.065*
C30.4046 (3)0.1541 (2)0.00321 (19)0.0516 (5)
H30.46680.20620.05360.062*
C80.1118 (3)0.3834 (2)0.10763 (19)0.0545 (5)
H80.14070.42800.18460.065*
C90.1941 (3)0.4486 (2)0.0164 (2)0.0563 (5)
H90.28010.53750.03050.068*
C20.4379 (3)0.2060 (2)0.1190 (2)0.0531 (5)
H20.52250.29380.14170.064*
H1WB0.141 (3)0.002 (3)0.437 (2)0.055 (7)*
H1WA0.005 (3)0.099 (3)0.403 (2)0.061 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03840 (13)0.03370 (12)0.02642 (11)0.00101 (8)0.00770 (8)0.01219 (8)
O1W0.0400 (7)0.0387 (7)0.0274 (6)0.0051 (5)0.0041 (5)0.0095 (5)
O40.0419 (7)0.0511 (7)0.0321 (6)0.0148 (6)0.0034 (5)0.0137 (5)
O10.0592 (9)0.0546 (8)0.0557 (9)0.0121 (7)0.0151 (7)0.0361 (7)
O30.0701 (9)0.0433 (7)0.0408 (7)0.0065 (6)0.0218 (7)0.0061 (6)
N20.0411 (8)0.0337 (7)0.0306 (7)0.0081 (6)0.0073 (6)0.0076 (6)
N10.0370 (7)0.0375 (7)0.0300 (7)0.0074 (6)0.0019 (5)0.0129 (6)
C110.0418 (9)0.0391 (9)0.0259 (8)0.0191 (7)0.0054 (6)0.0061 (7)
C160.0330 (8)0.0337 (8)0.0323 (8)0.0024 (6)0.0036 (6)0.0179 (7)
O20.0902 (12)0.0378 (7)0.0420 (8)0.0069 (7)0.0063 (7)0.0110 (6)
C120.0396 (9)0.0392 (9)0.0266 (8)0.0183 (7)0.0015 (6)0.0123 (7)
C70.0572 (11)0.0524 (11)0.0289 (9)0.0303 (9)0.0099 (8)0.0035 (8)
C170.0323 (8)0.0394 (9)0.0456 (10)0.0001 (7)0.0061 (7)0.0204 (8)
C130.0368 (9)0.0340 (9)0.0413 (9)0.0059 (7)0.0001 (7)0.0170 (7)
C40.0501 (10)0.0498 (10)0.0351 (9)0.0258 (9)0.0081 (8)0.0207 (8)
C140.0616 (12)0.0329 (9)0.0374 (9)0.0016 (8)0.0067 (8)0.0143 (7)
C180.0427 (9)0.0368 (9)0.0423 (10)0.0007 (7)0.0151 (7)0.0167 (7)
C150.0425 (9)0.0350 (9)0.0401 (9)0.0002 (7)0.0094 (7)0.0158 (7)
C10.0431 (10)0.0426 (10)0.0403 (10)0.0036 (8)0.0047 (7)0.0137 (8)
C100.0512 (11)0.0386 (9)0.0455 (10)0.0053 (8)0.0124 (8)0.0067 (8)
C60.0785 (15)0.0691 (14)0.0253 (9)0.0424 (12)0.0057 (9)0.0096 (9)
C50.0761 (14)0.0713 (14)0.0303 (9)0.0399 (12)0.0087 (9)0.0267 (9)
C30.0546 (11)0.0538 (12)0.0509 (12)0.0178 (9)0.0121 (9)0.0318 (10)
C80.0681 (13)0.0558 (12)0.0396 (10)0.0242 (10)0.0252 (10)0.0075 (9)
C90.0603 (13)0.0457 (11)0.0548 (13)0.0082 (9)0.0239 (10)0.0033 (9)
C20.0456 (11)0.0456 (11)0.0644 (13)0.0033 (8)0.0020 (9)0.0260 (10)
Geometric parameters (Å, º) top
Zn1—O12.0161 (13)C13—C141.516 (2)
Zn1—O1W2.0361 (13)C4—C31.404 (3)
Zn1—O42.0663 (12)C4—C51.434 (3)
Zn1—N22.1249 (14)C14—C151.510 (2)
Zn1—N12.2162 (14)C14—H14B0.9700
Zn1—O32.4441 (15)C14—H14A0.9700
Zn1—C162.5879 (17)C18—C15i1.521 (2)
O1W—H1WB0.77 (3)C18—H18A0.9700
O1W—H1WA0.85 (3)C18—H18B0.9700
O4—C161.274 (2)C15—C18i1.521 (2)
O1—C131.258 (2)C15—H15A0.9700
O3—C161.240 (2)C15—H15B0.9700
N2—C101.329 (2)C1—C21.397 (3)
N2—C111.356 (2)C1—H10.9300
N1—C11.323 (2)C10—C91.397 (3)
N1—C121.350 (2)C10—H100.9300
C11—C71.408 (2)C6—C51.339 (3)
C11—C121.441 (2)C6—H60.9300
C16—C171.506 (2)C5—H50.9300
O2—C131.236 (2)C3—C21.366 (3)
C12—C41.406 (2)C3—H30.9300
C7—C81.400 (3)C8—C91.360 (3)
C7—C61.434 (3)C8—H80.9300
C17—C181.528 (2)C9—H90.9300
C17—H17A0.9700C2—H20.9300
C17—H17B0.9700
O1—Zn1—O1W96.49 (6)C16—C17—H17B109.3
O1—Zn1—O4101.27 (5)C18—C17—H17B109.3
O1W—Zn1—O4101.71 (5)H17A—C17—H17B108.0
O1—Zn1—N289.21 (6)O2—C13—O1126.37 (17)
O1W—Zn1—N2106.66 (5)O2—C13—C14119.28 (15)
O4—Zn1—N2148.38 (5)O1—C13—C14114.35 (16)
O1—Zn1—N1165.55 (6)C3—C4—C12116.87 (17)
O1W—Zn1—N188.77 (5)C3—C4—C5124.29 (18)
O4—Zn1—N190.76 (5)C12—C4—C5118.84 (19)
N2—Zn1—N176.37 (5)C15—C14—C13117.00 (16)
O1—Zn1—O393.97 (6)C15—C14—H14B108.0
O1W—Zn1—O3158.19 (5)C13—C14—H14B108.0
O4—Zn1—O357.35 (5)C15—C14—H14A108.0
N2—Zn1—O392.53 (5)C13—C14—H14A108.0
N1—Zn1—O385.75 (5)H14B—C14—H14A107.3
O1—Zn1—C1696.77 (6)C15i—C18—C17114.13 (15)
O1W—Zn1—C16130.77 (5)C15i—C18—H18A108.7
O4—Zn1—C1629.10 (5)C17—C18—H18A108.7
N2—Zn1—C16120.70 (5)C15i—C18—H18B108.7
N1—Zn1—C1689.84 (5)C17—C18—H18B108.7
O3—Zn1—C1628.36 (5)H18A—C18—H18B107.6
Zn1—O1W—H1WB118.1 (17)C14—C15—C18i111.63 (15)
Zn1—O1W—H1WA113.0 (16)C14—C15—H15A109.3
H1WB—O1W—H1WA108 (2)C18i—C15—H15A109.3
C16—O4—Zn198.80 (10)C14—C15—H15B109.3
C13—O1—Zn1140.64 (13)C18i—C15—H15B109.3
C16—O3—Zn182.27 (11)H15A—C15—H15B108.0
C10—N2—C11118.11 (16)N1—C1—C2122.70 (18)
C10—N2—Zn1126.04 (13)N1—C1—H1118.6
C11—N2—Zn1115.81 (11)C2—C1—H1118.6
C1—N1—C12118.27 (15)N2—C10—C9122.6 (2)
C1—N1—Zn1128.68 (12)N2—C10—H10118.7
C12—N1—Zn1113.04 (11)C9—C10—H10118.7
N2—C11—C7122.69 (17)C5—C6—C7121.28 (18)
N2—C11—C12117.39 (14)C5—C6—H6119.4
C7—C11—C12119.91 (16)C7—C6—H6119.4
O3—C16—O4121.11 (16)C6—C5—C4121.66 (18)
O3—C16—C17121.21 (16)C6—C5—H5119.2
O4—C16—C17117.67 (15)C4—C5—H5119.2
O3—C16—Zn169.37 (10)C2—C3—C4119.69 (17)
O4—C16—Zn152.10 (8)C2—C3—H3120.2
C17—C16—Zn1167.53 (12)C4—C3—H3120.2
N1—C12—C4123.15 (17)C9—C8—C7119.80 (18)
N1—C12—C11117.31 (14)C9—C8—H8120.1
C4—C12—C11119.54 (16)C7—C8—H8120.1
C8—C7—C11117.27 (18)C8—C9—C10119.5 (2)
C8—C7—C6123.99 (18)C8—C9—H9120.2
C11—C7—C6118.74 (19)C10—C9—H9120.2
C16—C17—C18111.58 (14)C3—C2—C1119.32 (19)
C16—C17—H17A109.3C3—C2—H2120.3
C18—C17—H17A109.3C1—C2—H2120.3
O1—Zn1—O4—C1683.64 (10)O1—Zn1—C16—O4101.03 (10)
O1W—Zn1—O4—C16177.21 (9)O1W—Zn1—C16—O43.61 (12)
N2—Zn1—O4—C1623.64 (15)N2—Zn1—C16—O4165.85 (9)
N1—Zn1—O4—C1688.30 (10)N1—Zn1—C16—O491.85 (10)
O3—Zn1—O4—C163.85 (9)O3—Zn1—C16—O4173.17 (15)
O1W—Zn1—O1—C1379.1 (2)O1—Zn1—C16—C1763.7 (5)
O4—Zn1—O1—C1324.3 (2)O1W—Zn1—C16—C1740.9 (5)
N2—Zn1—O1—C13174.2 (2)O4—Zn1—C16—C1737.3 (5)
N1—Zn1—O1—C13170.13 (19)N2—Zn1—C16—C17156.8 (5)
O3—Zn1—O1—C1381.8 (2)N1—Zn1—C16—C17129.2 (5)
C16—Zn1—O1—C1353.4 (2)O3—Zn1—C16—C17149.5 (6)
O1—Zn1—O3—C1696.91 (10)C1—N1—C12—C40.1 (2)
O1W—Zn1—O3—C1621.68 (19)Zn1—N1—C12—C4178.89 (12)
O4—Zn1—O3—C163.94 (9)C1—N1—C12—C11179.96 (15)
N2—Zn1—O3—C16173.70 (10)Zn1—N1—C12—C111.06 (18)
N1—Zn1—O3—C1697.58 (10)N2—C11—C12—N11.0 (2)
O1—Zn1—N2—C100.94 (15)C7—C11—C12—N1179.67 (14)
O1W—Zn1—N2—C1095.60 (15)N2—C11—C12—C4179.08 (14)
O4—Zn1—N2—C10111.46 (16)C7—C11—C12—C40.3 (2)
N1—Zn1—N2—C10179.89 (16)N2—C11—C7—C81.3 (3)
O3—Zn1—N2—C1094.88 (15)C12—C11—C7—C8179.33 (16)
C16—Zn1—N2—C1098.36 (15)N2—C11—C7—C6177.65 (15)
O1—Zn1—N2—C11176.60 (12)C12—C11—C7—C61.7 (2)
O1W—Zn1—N2—C1186.86 (12)O3—C16—C17—C18108.49 (18)
O4—Zn1—N2—C1166.08 (16)O4—C16—C17—C1870.48 (19)
N1—Zn1—N2—C112.34 (11)Zn1—C16—C17—C1837.8 (6)
O3—Zn1—N2—C1182.66 (12)Zn1—O1—C13—O217.5 (4)
C16—Zn1—N2—C1179.19 (12)Zn1—O1—C13—C14162.58 (17)
O1—Zn1—N1—C1176.4 (2)N1—C12—C4—C30.6 (2)
O1W—Zn1—N1—C171.88 (15)C11—C12—C4—C3179.38 (15)
O4—Zn1—N1—C129.82 (15)N1—C12—C4—C5178.80 (15)
N2—Zn1—N1—C1179.36 (16)C11—C12—C4—C51.2 (2)
O3—Zn1—N1—C187.00 (15)O2—C13—C14—C152.2 (3)
C16—Zn1—N1—C158.91 (15)O1—C13—C14—C15177.71 (17)
O1—Zn1—N1—C122.5 (3)C16—C17—C18—C15i62.2 (2)
O1W—Zn1—N1—C12109.27 (11)C13—C14—C15—C18i175.59 (16)
O4—Zn1—N1—C12149.03 (11)C12—N1—C1—C20.6 (3)
N2—Zn1—N1—C121.79 (11)Zn1—N1—C1—C2178.18 (14)
O3—Zn1—N1—C1291.85 (11)C11—N2—C10—C90.7 (3)
C16—Zn1—N1—C12119.94 (11)Zn1—N2—C10—C9176.83 (15)
C10—N2—C11—C70.3 (2)C8—C7—C6—C5179.52 (19)
Zn1—N2—C11—C7178.05 (12)C11—C7—C6—C51.6 (3)
C10—N2—C11—C12179.64 (15)C7—C6—C5—C40.0 (3)
Zn1—N2—C11—C122.61 (18)C3—C4—C5—C6179.27 (19)
Zn1—O3—C16—O46.29 (14)C12—C4—C5—C61.4 (3)
Zn1—O3—C16—C17172.64 (14)C12—C4—C3—C20.7 (3)
Zn1—O4—C16—O37.47 (17)C5—C4—C3—C2178.62 (19)
Zn1—O4—C16—C17171.50 (11)C11—C7—C8—C91.4 (3)
O1—Zn1—C16—O385.80 (10)C6—C7—C8—C9177.50 (19)
O1W—Zn1—C16—O3169.56 (9)C7—C8—C9—C100.6 (3)
O4—Zn1—C16—O3173.17 (15)N2—C10—C9—C80.5 (3)
N2—Zn1—C16—O37.32 (12)C4—C3—C2—C10.2 (3)
N1—Zn1—C16—O381.32 (10)N1—C1—C2—C30.5 (3)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O10.932.493.030 (3)117
O1W—H1WB···O4ii0.77 (2)2.06 (2)2.750 (2)148 (3)
O1W—H1WA···O2ii0.85 (3)1.74 (3)2.588 (2)173 (3)
C3—H3···O3iii0.932.523.402 (3)158
C9—H9···O3iv0.932.503.142 (3)126
Symmetry codes: (ii) x, y, z+1; (iii) x+1, y, z; (iv) x, y+1, z.
 

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