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In the mol­ecule of the title compound, [Zn(C7H5O2)2(C12H8N2)], the coordination about the ZnII center is best described as distorted octa­hedral. The crystal structure is stabilized by π–π stacking of neighboring phenyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600907X/hk2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600907X/hk2012Isup2.hkl
Contains datablock I

CCDC reference: 274554

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.054
  • wR factor = 0.146
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O2 .. 8.29 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Dibenzoato(1,10-phenanthroline)Zinc(II) top
Crystal data top
[Zn(C7H5O2)2(C12H8N2)]F(000) = 1000
Mr = 487.79Dx = 1.453 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2907 reflections
a = 7.5698 (9) Åθ = 2.3–23.5°
b = 16.7052 (19) ŵ = 1.14 mm1
c = 18.017 (2) ÅT = 292 K
β = 101.813 (2)°Needle, colorless
V = 2230.1 (4) Å30.60 × 0.14 × 0.06 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4855 independent reflections
Radiation source: fine-focus sealed tube3389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.549, Tmax = 0.935k = 2113
12837 measured reflectionsl = 2322
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0444P)2 + 2.2799P]
where P = (Fo2 + 2Fc2)/3
4855 reflections(Δ/σ)max = 0.002
298 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.26 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
Zn10.83823 (6)0.13558 (3)0.15680 (3)0.05149 (18)
N10.8212 (4)0.0961 (2)0.04438 (19)0.0474 (8)
N20.7534 (4)0.0154 (2)0.16384 (19)0.0505 (8)
O11.1106 (4)0.13770 (19)0.19795 (16)0.0599 (8)
O20.9508 (4)0.1546 (2)0.28426 (19)0.0756 (10)
O30.7966 (4)0.27455 (18)0.11699 (18)0.0640 (8)
O40.6082 (4)0.19376 (16)0.15732 (16)0.0526 (7)
C11.0987 (6)0.1487 (2)0.2662 (2)0.0516 (10)
C21.2699 (5)0.1530 (2)0.3263 (2)0.0432 (9)
C31.4369 (6)0.1471 (3)0.3065 (2)0.0556 (11)
H31.44420.14250.25580.067*
C41.5903 (6)0.1482 (3)0.3614 (3)0.0673 (13)
H41.70220.14620.34770.081*
C51.5818 (7)0.1521 (3)0.4370 (3)0.0657 (13)
H51.68700.15120.47420.079*
C61.4139 (7)0.1575 (3)0.4572 (2)0.0583 (11)
H61.40610.16010.50800.070*
C71.2595 (6)0.1588 (2)0.4013 (2)0.0497 (10)
H71.14740.16360.41440.060*
C80.6476 (5)0.2617 (2)0.1330 (2)0.0470 (9)
C90.5085 (5)0.3261 (2)0.1268 (2)0.0458 (9)
C100.5393 (6)0.4005 (3)0.0973 (3)0.0611 (11)
H100.64450.40950.07940.073*
C110.4148 (7)0.4608 (3)0.0944 (3)0.0769 (15)
H110.43750.51100.07610.092*
C120.2551 (7)0.4469 (3)0.1187 (3)0.0779 (15)
H120.17040.48770.11610.093*
C130.2220 (7)0.3743 (3)0.1462 (3)0.0736 (14)
H130.11430.36540.16210.088*
C140.3479 (6)0.3125 (3)0.1508 (3)0.0595 (11)
H140.32460.26270.16980.071*
C150.8545 (6)0.1377 (3)0.0142 (3)0.0575 (11)
H150.89060.19080.00660.069*
C160.8378 (6)0.1055 (4)0.0857 (3)0.0685 (14)
H160.86280.13660.12510.082*
C170.7848 (6)0.0282 (3)0.0983 (3)0.0634 (13)
H170.77310.00600.14640.076*
C180.7479 (5)0.0177 (3)0.0379 (2)0.0531 (10)
C190.6928 (6)0.1005 (3)0.0439 (3)0.0667 (13)
H190.68150.12650.09030.080*
C200.6583 (6)0.1402 (3)0.0143 (3)0.0679 (13)
H200.62090.19320.00760.082*
C210.6761 (5)0.1046 (2)0.0879 (3)0.0547 (11)
C220.6444 (6)0.1436 (3)0.1521 (3)0.0675 (13)
H220.60970.19710.14910.081*
C230.6637 (7)0.1042 (3)0.2182 (3)0.0733 (14)
H230.63930.12990.26080.088*
C240.7207 (6)0.0247 (3)0.2226 (3)0.0648 (12)
H240.73640.00120.26920.078*
C250.7312 (5)0.0242 (2)0.0964 (2)0.0460 (9)
C260.7679 (5)0.0197 (2)0.0331 (2)0.0428 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0519 (3)0.0479 (3)0.0538 (3)0.0042 (2)0.0086 (2)0.0074 (2)
N10.0477 (19)0.0435 (19)0.0513 (19)0.0062 (15)0.0108 (15)0.0021 (16)
N20.052 (2)0.048 (2)0.051 (2)0.0064 (16)0.0091 (16)0.0030 (16)
O10.0614 (18)0.070 (2)0.0467 (17)0.0009 (16)0.0076 (14)0.0012 (15)
O20.0468 (18)0.109 (3)0.073 (2)0.0041 (17)0.0158 (16)0.0123 (19)
O30.0600 (19)0.0580 (19)0.081 (2)0.0017 (15)0.0312 (17)0.0014 (16)
O40.0576 (17)0.0433 (16)0.0589 (18)0.0054 (13)0.0163 (14)0.0024 (13)
C10.057 (3)0.041 (2)0.058 (3)0.0016 (19)0.014 (2)0.0015 (19)
C20.050 (2)0.034 (2)0.049 (2)0.0022 (16)0.0160 (18)0.0017 (16)
C30.057 (3)0.064 (3)0.048 (2)0.003 (2)0.018 (2)0.004 (2)
C40.048 (3)0.085 (4)0.070 (3)0.004 (2)0.016 (2)0.000 (3)
C50.059 (3)0.071 (3)0.062 (3)0.009 (2)0.001 (2)0.005 (2)
C60.081 (3)0.051 (3)0.045 (2)0.002 (2)0.017 (2)0.0075 (19)
C70.057 (3)0.043 (2)0.053 (2)0.0027 (18)0.022 (2)0.0074 (18)
C80.055 (2)0.050 (2)0.037 (2)0.0012 (19)0.0109 (18)0.0049 (18)
C90.053 (2)0.041 (2)0.042 (2)0.0008 (18)0.0072 (18)0.0014 (17)
C100.062 (3)0.054 (3)0.067 (3)0.000 (2)0.014 (2)0.000 (2)
C110.085 (4)0.044 (3)0.102 (4)0.002 (3)0.022 (3)0.004 (3)
C120.078 (4)0.052 (3)0.102 (4)0.019 (3)0.017 (3)0.011 (3)
C130.060 (3)0.068 (3)0.099 (4)0.010 (2)0.029 (3)0.004 (3)
C140.062 (3)0.049 (3)0.070 (3)0.004 (2)0.018 (2)0.000 (2)
C150.056 (3)0.055 (3)0.065 (3)0.009 (2)0.018 (2)0.008 (2)
C160.057 (3)0.097 (4)0.054 (3)0.017 (3)0.019 (2)0.015 (3)
C170.050 (3)0.086 (4)0.054 (3)0.015 (2)0.011 (2)0.008 (3)
C180.039 (2)0.061 (3)0.056 (3)0.0085 (19)0.0024 (19)0.011 (2)
C190.058 (3)0.070 (3)0.071 (3)0.003 (2)0.010 (2)0.028 (3)
C200.052 (3)0.052 (3)0.100 (4)0.003 (2)0.015 (3)0.019 (3)
C210.040 (2)0.040 (2)0.082 (3)0.0014 (18)0.008 (2)0.002 (2)
C220.056 (3)0.048 (3)0.098 (4)0.001 (2)0.016 (3)0.010 (3)
C230.066 (3)0.073 (4)0.084 (4)0.009 (3)0.023 (3)0.033 (3)
C240.069 (3)0.068 (3)0.056 (3)0.008 (2)0.010 (2)0.006 (2)
C250.0339 (19)0.047 (2)0.055 (2)0.0080 (17)0.0050 (17)0.0004 (19)
C260.0344 (19)0.043 (2)0.050 (2)0.0069 (16)0.0063 (16)0.0006 (17)
Geometric parameters (Å, º) top
Zn1—O41.996 (3)C10—C111.372 (6)
Zn1—O12.044 (3)C10—H100.9300
Zn1—N12.109 (3)C11—C121.387 (7)
Zn1—N22.120 (3)C11—H110.9300
Zn1—O22.302 (3)C12—C131.353 (7)
Zn1—O32.431 (3)C12—H120.9300
N1—C151.330 (5)C13—C141.396 (6)
N1—C261.343 (5)C13—H130.9300
N2—C241.319 (5)C14—H140.9300
N2—C251.363 (5)C15—C161.376 (6)
O1—C11.265 (5)C15—H150.9300
O2—C11.232 (5)C16—C171.357 (7)
O3—C81.239 (5)C16—H160.9300
O4—C81.273 (5)C17—C181.406 (6)
C1—C21.511 (6)C17—H170.9300
C2—C71.372 (5)C18—C261.404 (5)
C2—C31.385 (5)C18—C191.442 (6)
C3—C41.363 (6)C19—C201.311 (7)
C3—H30.9300C19—H190.9300
C4—C51.379 (7)C20—C211.435 (7)
C4—H40.9300C20—H200.9300
C5—C61.394 (6)C21—C221.389 (7)
C5—H50.9300C21—C251.404 (6)
C6—C71.378 (6)C22—C231.342 (7)
C6—H60.9300C22—H220.9300
C7—H70.9300C23—C241.393 (7)
C8—C91.494 (6)C23—H230.9300
C9—C141.390 (6)C24—H240.9300
C9—C101.391 (6)C25—C261.431 (5)
O4—Zn1—O1143.73 (12)C11—C10—C9120.2 (4)
O4—Zn1—N1105.95 (12)C11—C10—H10119.9
O1—Zn1—N1102.28 (12)C9—C10—H10119.9
O4—Zn1—N2100.70 (12)C10—C11—C12120.1 (5)
O1—Zn1—N2106.87 (12)C10—C11—H11119.9
N1—Zn1—N278.57 (13)C12—C11—H11119.9
O4—Zn1—O294.20 (11)C13—C12—C11120.3 (5)
O1—Zn1—O259.72 (11)C13—C12—H12119.9
N1—Zn1—O2159.83 (12)C11—C12—H12119.9
N2—Zn1—O297.23 (13)C12—C13—C14120.6 (5)
O4—Zn1—O358.39 (11)C12—C13—H13119.7
O1—Zn1—O398.67 (11)C14—C13—H13119.7
N1—Zn1—O392.08 (12)C9—C14—C13119.4 (4)
N2—Zn1—O3154.10 (12)C9—C14—H14120.3
O2—Zn1—O399.31 (12)C13—C14—H14120.3
C15—N1—C26118.4 (4)N1—C15—C16122.9 (5)
C15—N1—Zn1128.0 (3)N1—C15—H15118.6
C26—N1—Zn1113.6 (3)C16—C15—H15118.6
C24—N2—C25117.4 (4)C17—C16—C15119.7 (5)
C24—N2—Zn1129.7 (3)C17—C16—H16120.2
C25—N2—Zn1113.0 (3)C15—C16—H16120.2
C1—O1—Zn195.0 (3)C16—C17—C18119.3 (4)
C1—O2—Zn184.0 (3)C16—C17—H17120.4
C8—O3—Zn180.5 (2)C18—C17—H17120.4
C8—O4—Zn199.6 (2)C26—C18—C17117.4 (4)
O2—C1—O1121.2 (4)C26—C18—C19118.1 (4)
O2—C1—C2120.0 (4)C17—C18—C19124.5 (4)
O1—C1—C2118.8 (4)C20—C19—C18121.8 (5)
C7—C2—C3119.8 (4)C20—C19—H19119.1
C7—C2—C1119.7 (4)C18—C19—H19119.1
C3—C2—C1120.4 (4)C19—C20—C21122.2 (5)
C4—C3—C2120.0 (4)C19—C20—H20118.9
C4—C3—H3120.0C21—C20—H20118.9
C2—C3—H3120.0C22—C21—C25117.1 (4)
C3—C4—C5120.8 (4)C22—C21—C20125.1 (4)
C3—C4—H4119.6C25—C21—C20117.8 (4)
C5—C4—H4119.6C23—C22—C21120.1 (5)
C4—C5—C6119.3 (4)C23—C22—H22119.9
C4—C5—H5120.3C21—C22—H22119.9
C6—C5—H5120.3C22—C23—C24119.6 (5)
C7—C6—C5119.5 (4)C22—C23—H23120.2
C7—C6—H6120.2C24—C23—H23120.2
C5—C6—H6120.2N2—C24—C23123.0 (5)
C2—C7—C6120.5 (4)N2—C24—H24118.5
C2—C7—H7119.8C23—C24—H24118.5
C6—C7—H7119.8N2—C25—C21122.7 (4)
O3—C8—O4121.6 (4)N2—C25—C26117.0 (4)
O3—C8—C9121.2 (4)C21—C25—C26120.3 (4)
O4—C8—C9117.2 (3)N1—C26—C18122.3 (4)
C14—C9—C10119.4 (4)N1—C26—C25117.9 (4)
C14—C9—C8120.5 (4)C18—C26—C25119.8 (4)
C10—C9—C8120.2 (4)
O4—Zn1—N1—C1581.5 (3)C5—C6—C7—C21.5 (6)
O1—Zn1—N1—C1575.5 (3)Zn1—O3—C8—O40.1 (3)
N2—Zn1—N1—C15179.5 (3)Zn1—O3—C8—C9178.1 (3)
O2—Zn1—N1—C15100.8 (5)Zn1—O4—C8—O30.1 (4)
O3—Zn1—N1—C1523.8 (3)Zn1—O4—C8—C9178.2 (3)
O4—Zn1—N1—C2697.7 (3)O3—C8—C9—C14174.7 (4)
O1—Zn1—N1—C26105.3 (3)O4—C8—C9—C143.4 (6)
N2—Zn1—N1—C260.3 (2)O3—C8—C9—C104.9 (6)
O2—Zn1—N1—C2680.0 (5)O4—C8—C9—C10177.0 (4)
O3—Zn1—N1—C26155.4 (3)C14—C9—C10—C112.3 (7)
O4—Zn1—N2—C2476.1 (4)C8—C9—C10—C11177.4 (4)
O1—Zn1—N2—C2480.1 (4)C9—C10—C11—C122.0 (8)
N1—Zn1—N2—C24179.6 (4)C10—C11—C12—C130.7 (8)
O2—Zn1—N2—C2419.6 (4)C11—C12—C13—C140.3 (9)
O3—Zn1—N2—C24109.8 (4)C10—C9—C14—C131.2 (7)
O4—Zn1—N2—C25104.1 (3)C8—C9—C14—C13178.5 (4)
O1—Zn1—N2—C2599.8 (3)C12—C13—C14—C90.1 (8)
N1—Zn1—N2—C250.3 (2)C26—N1—C15—C160.4 (6)
O2—Zn1—N2—C25160.3 (3)Zn1—N1—C15—C16179.6 (3)
O3—Zn1—N2—C2570.4 (4)N1—C15—C16—C170.2 (7)
O4—Zn1—O1—C149.6 (3)C15—C16—C17—C180.0 (7)
N1—Zn1—O1—C1169.9 (2)C16—C17—C18—C260.1 (6)
N2—Zn1—O1—C188.3 (3)C16—C17—C18—C19179.2 (4)
O2—Zn1—O1—C10.3 (2)C26—C18—C19—C201.4 (7)
O3—Zn1—O1—C196.1 (2)C17—C18—C19—C20179.3 (4)
O4—Zn1—O2—C1153.6 (3)C18—C19—C20—C211.2 (7)
O1—Zn1—O2—C10.3 (2)C19—C20—C21—C22179.0 (4)
N1—Zn1—O2—C128.6 (5)C19—C20—C21—C250.5 (7)
N2—Zn1—O2—C1105.0 (3)C25—C21—C22—C231.1 (6)
O3—Zn1—O2—C195.0 (3)C20—C21—C22—C23179.4 (4)
O4—Zn1—O3—C80.1 (2)C21—C22—C23—C241.8 (7)
O1—Zn1—O3—C8149.8 (2)C25—N2—C24—C230.7 (6)
N1—Zn1—O3—C8107.4 (2)Zn1—N2—C24—C23179.5 (3)
N2—Zn1—O3—C839.7 (4)C22—C23—C24—N21.6 (7)
O2—Zn1—O3—C889.3 (2)C24—N2—C25—C210.1 (6)
O1—Zn1—O4—C857.4 (3)Zn1—N2—C25—C21179.8 (3)
N1—Zn1—O4—C882.4 (2)C24—N2—C25—C26179.7 (3)
N2—Zn1—O4—C8163.4 (2)Zn1—N2—C25—C260.2 (4)
O2—Zn1—O4—C898.4 (2)C22—C21—C25—N20.1 (6)
O3—Zn1—O4—C80.0 (2)C20—C21—C25—N2179.7 (4)
Zn1—O2—C1—O10.5 (4)C22—C21—C25—C26179.5 (4)
Zn1—O2—C1—C2178.3 (3)C20—C21—C25—C260.1 (5)
Zn1—O1—C1—O20.6 (4)C15—N1—C26—C180.6 (5)
Zn1—O1—C1—C2178.3 (3)Zn1—N1—C26—C18179.9 (3)
O2—C1—C2—C73.8 (6)C15—N1—C26—C25179.5 (3)
O1—C1—C2—C7175.0 (4)Zn1—N1—C26—C250.2 (4)
O2—C1—C2—C3179.4 (4)C17—C18—C26—N10.4 (6)
O1—C1—C2—C31.7 (6)C19—C18—C26—N1179.0 (4)
C7—C2—C3—C40.9 (6)C17—C18—C26—C25179.7 (3)
C1—C2—C3—C4177.6 (4)C19—C18—C26—C250.9 (5)
C2—C3—C4—C52.4 (7)N2—C25—C26—N10.0 (5)
C3—C4—C5—C61.9 (7)C21—C25—C26—N1179.6 (3)
C4—C5—C6—C70.1 (7)N2—C25—C26—C18179.9 (3)
C3—C2—C7—C61.1 (6)C21—C25—C26—C180.3 (5)
C1—C2—C7—C6175.7 (4)
 

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