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The title compound, [Zn(C7H3FO2)2(C5H6N2)2], is a mononuclear zinc(II) compound. The ZnII atom is coordinated by two N atoms from two 2-amino­pyridine ligands and two O atoms from two 2-fluoro­benzoate anions in a distorted tetrahedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018884/ci6416sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018884/ci6416Isup2.hkl
Contains datablock I

CCDC reference: 251577

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.126
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9 - C10 ... 1.38 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C9 - C14 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C10 - C11 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.37 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 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 12 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis(2-aminopyridine-κN1)bis(2-fluorobenzoato-κO)zinc(II) top
Crystal data top
[Zn(C7H3FO2)2(C5H6N2)2]F(000) = 1088
Mr = 531.81Dx = 1.492 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5568 reflections
a = 9.126 (2) Åθ = 2.5–26.7°
b = 11.102 (2) ŵ = 1.09 mm1
c = 23.411 (2) ÅT = 293 K
β = 93.707 (3)°Block, colourless
V = 2367.0 (7) Å30.32 × 0.22 × 0.21 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
4894 independent reflections
Radiation source: fine-focus sealed tube3969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.721, Tmax = 0.803k = 1213
13644 measured reflectionsl = 1929
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0735P)2 + 0.5892P]
where P = (Fo2 + 2Fc2)/3
4894 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.55 e Å3
5 restraintsΔρmin = 0.23 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*/UeqOcc. (<1)
Zn10.81247 (3)0.92808 (3)0.621440 (11)0.06543 (14)
F11.0661 (4)0.8290 (4)0.78092 (14)0.1189 (12)0.64
F20.7545 (5)1.3817 (4)0.64719 (19)0.1385 (15)0.64
F1'1.3431 (7)1.0883 (5)0.6658 (3)0.122 (2)0.36
F2'0.4915 (10)1.1349 (6)0.5270 (3)0.165 (3)0.36
O11.0907 (3)1.0317 (2)0.63424 (9)0.1038 (7)
O20.9617 (2)0.9128 (2)0.68517 (8)0.0837 (6)
O30.7146 (3)1.05999 (18)0.57707 (10)0.0882 (6)
O40.7461 (3)1.1321 (3)0.66251 (11)0.1160 (9)
N10.8969 (2)0.81817 (19)0.56022 (8)0.0628 (5)
N20.8348 (3)0.9384 (2)0.48184 (9)0.0713 (6)
H2A0.78470.98350.50320.086*
H2B0.83940.95500.44610.086*
N30.6345 (2)0.83271 (19)0.64657 (8)0.0634 (5)
N40.7488 (3)0.7588 (3)0.72973 (11)0.0985 (9)
H4A0.82830.79450.72140.118*
H4B0.74690.71740.76070.118*
C11.0780 (3)0.9714 (2)0.67709 (10)0.0653 (6)
C21.1992 (3)0.9647 (2)0.72305 (11)0.0660 (6)
C31.3290 (4)1.0266 (3)0.71668 (17)0.0941 (10)
H31.34091.07360.68440.113*0.64
C41.4446 (4)1.0169 (5)0.7608 (3)0.1264 (17)
H41.53231.05820.75760.152*
C51.4256 (6)0.9478 (6)0.8069 (3)0.134 (2)
H51.50190.94140.83500.161*
C61.3020 (5)0.8885 (5)0.81357 (17)0.1142 (14)
H61.29200.84230.84620.137*
C71.1879 (3)0.8954 (3)0.77206 (12)0.0810 (8)
H71.10180.85280.77690.097*0.36
C80.6990 (3)1.1422 (2)0.61315 (12)0.0768 (7)
C90.6101 (3)1.2508 (2)0.59234 (12)0.0701 (7)
C100.4934 (5)1.2440 (3)0.55218 (16)0.1016 (11)
H100.47131.17010.53500.122*0.64
C110.4082 (5)1.3416 (5)0.5364 (2)0.1287 (16)
H110.33001.33290.50920.154*
C120.4378 (5)1.4505 (5)0.5603 (2)0.1199 (15)
H120.37761.51600.55070.144*
C130.5550 (5)1.4644 (4)0.5981 (2)0.1104 (13)
H130.58031.53970.61300.132*
C140.6354 (4)1.3638 (3)0.61381 (15)0.0944 (10)
H140.71311.37340.64120.113*0.36
C150.9638 (3)0.7176 (3)0.58155 (13)0.0800 (7)
H150.95530.70030.62010.096*
C161.0418 (4)0.6408 (3)0.55093 (16)0.0911 (9)
H161.08550.57250.56760.109*
C171.0544 (4)0.6678 (3)0.49303 (16)0.0886 (9)
H171.10870.61780.47060.106*
C180.9879 (3)0.7663 (3)0.46983 (12)0.0765 (7)
H180.99590.78420.43130.092*
C190.9058 (3)0.8423 (2)0.50421 (10)0.0602 (6)
C200.5122 (3)0.8397 (3)0.61086 (13)0.0760 (7)
H200.51580.88620.57790.091*
C210.3844 (3)0.7825 (3)0.62045 (16)0.0866 (8)
H210.30330.78820.59440.104*
C220.3789 (4)0.7156 (3)0.67015 (17)0.0906 (9)
H220.29290.67600.67820.109*
C230.4985 (4)0.7082 (3)0.70681 (14)0.0830 (8)
H230.49480.66360.74030.100*
C240.6288 (3)0.7676 (2)0.69464 (11)0.0690 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0777 (2)0.0776 (2)0.04124 (18)0.01504 (14)0.00590 (13)0.00025 (11)
F10.107 (2)0.165 (3)0.0838 (19)0.015 (2)0.0008 (16)0.045 (2)
F20.147 (3)0.110 (2)0.148 (3)0.020 (2)0.071 (3)0.018 (2)
F1'0.110 (4)0.105 (4)0.155 (6)0.039 (3)0.047 (4)0.002 (4)
F2'0.201 (8)0.134 (6)0.149 (7)0.037 (6)0.076 (6)0.003 (5)
O10.144 (2)0.1077 (16)0.0626 (12)0.0066 (15)0.0285 (13)0.0204 (12)
O20.0821 (13)0.1090 (16)0.0585 (11)0.0227 (11)0.0070 (9)0.0061 (10)
O30.1266 (18)0.0702 (12)0.0710 (13)0.0092 (11)0.0311 (12)0.0094 (9)
O40.141 (2)0.125 (2)0.0801 (16)0.0363 (18)0.0079 (14)0.0235 (15)
N10.0693 (12)0.0696 (12)0.0496 (10)0.0118 (10)0.0047 (9)0.0006 (9)
N20.0906 (16)0.0778 (15)0.0465 (11)0.0001 (11)0.0120 (10)0.0003 (9)
N30.0732 (12)0.0673 (12)0.0510 (10)0.0073 (10)0.0139 (9)0.0014 (9)
N40.1018 (18)0.124 (2)0.0700 (15)0.0182 (17)0.0069 (14)0.0356 (16)
C10.0812 (17)0.0682 (14)0.0478 (12)0.0027 (13)0.0148 (11)0.0075 (11)
C20.0661 (14)0.0692 (15)0.0640 (15)0.0025 (12)0.0132 (11)0.0198 (12)
C30.0785 (19)0.089 (2)0.117 (3)0.0104 (17)0.0225 (19)0.031 (2)
C40.066 (2)0.140 (4)0.173 (5)0.012 (2)0.012 (3)0.071 (4)
C50.092 (3)0.177 (5)0.129 (4)0.034 (3)0.024 (3)0.062 (4)
C60.097 (3)0.166 (4)0.078 (2)0.032 (3)0.0138 (19)0.015 (2)
C70.0747 (17)0.108 (2)0.0604 (16)0.0087 (16)0.0024 (13)0.0085 (15)
C80.0861 (18)0.0776 (18)0.0696 (17)0.0130 (14)0.0277 (14)0.0204 (14)
C90.0738 (15)0.0686 (16)0.0704 (15)0.0112 (12)0.0245 (13)0.0142 (12)
C100.122 (3)0.090 (2)0.091 (2)0.032 (2)0.007 (2)0.0010 (19)
C110.105 (3)0.136 (4)0.141 (4)0.027 (3)0.023 (3)0.035 (3)
C120.097 (3)0.118 (3)0.146 (4)0.010 (2)0.020 (3)0.020 (3)
C130.127 (3)0.073 (2)0.134 (3)0.010 (2)0.033 (3)0.022 (2)
C140.090 (2)0.093 (2)0.101 (2)0.0063 (18)0.0097 (18)0.0305 (19)
C150.0920 (19)0.0808 (19)0.0669 (16)0.0048 (16)0.0014 (14)0.0034 (14)
C160.089 (2)0.081 (2)0.104 (2)0.0057 (16)0.0057 (18)0.0028 (18)
C170.085 (2)0.081 (2)0.102 (2)0.0041 (16)0.0274 (17)0.0144 (18)
C180.0842 (17)0.0798 (18)0.0684 (16)0.0131 (15)0.0265 (13)0.0094 (14)
C190.0613 (13)0.0684 (15)0.0518 (12)0.0183 (11)0.0098 (10)0.0068 (11)
C200.0833 (18)0.0725 (17)0.0721 (16)0.0089 (14)0.0034 (13)0.0011 (13)
C210.0727 (17)0.0793 (19)0.108 (2)0.0062 (15)0.0062 (15)0.0070 (17)
C220.083 (2)0.0727 (18)0.120 (3)0.0140 (15)0.036 (2)0.0071 (18)
C230.099 (2)0.0689 (17)0.0851 (19)0.0087 (15)0.0372 (17)0.0052 (14)
C240.0827 (17)0.0651 (15)0.0613 (14)0.0019 (13)0.0204 (13)0.0002 (12)
Geometric parameters (Å, º) top
Zn1—O21.962 (2)C9—C141.365 (4)
Zn1—O31.975 (2)C9—C101.377 (4)
Zn1—N32.056 (2)C11—C121.352 (7)
Zn1—N12.069 (2)C11—C101.370 (6)
O1—C11.217 (3)C11—H110.93
O2—C11.269 (3)C12—C131.352 (6)
O3—C81.258 (3)C12—H120.93
O4—C81.212 (4)C13—C141.374 (6)
N1—C191.346 (3)C13—H130.93
N1—C151.352 (4)C15—C161.347 (5)
N2—C191.337 (3)C15—H150.93
N2—H2A0.86C16—C171.400 (5)
N2—H2B0.86C16—H160.93
N3—C241.341 (3)C17—C181.348 (5)
N3—C201.353 (4)C17—H170.93
N4—C241.329 (4)C18—C191.414 (4)
N4—H4A0.86C18—H180.93
N4—H4B0.86C20—C211.359 (4)
C1—C21.495 (4)C20—H200.93
C2—C31.386 (4)C21—C221.384 (5)
C2—C71.391 (4)C21—H210.93
C4—C51.344 (8)C22—C231.347 (5)
C4—C31.432 (6)C22—H220.93
C4—H40.93C23—C241.405 (4)
C5—C61.324 (8)C23—H230.93
C5—H50.93F1—C71.361 (3)
C6—C71.379 (5)F2—C141.312 (3)
C6—H60.93C3—H30.93
C8—C91.516 (3)C10—H100.93
O2—Zn1—O3137.10 (10)C11—C12—H12120.0
O2—Zn1—N3105.08 (9)C13—C12—H12120.0
O3—Zn1—N3101.15 (10)C12—C13—C14118.0 (4)
O2—Zn1—N1101.78 (9)C12—C13—H13121.0
O3—Zn1—N1104.43 (8)C14—C13—H13121.0
N3—Zn1—N1103.36 (8)C16—C15—N1124.6 (3)
C1—O2—Zn1112.83 (17)C16—C15—H15117.7
C8—O3—Zn1104.6 (2)N1—C15—H15117.7
C19—N1—C15118.0 (2)C15—C16—C17117.3 (3)
C19—N1—Zn1127.31 (18)C15—C16—H16121.4
C15—N1—Zn1114.24 (17)C17—C16—H16121.4
C19—N2—H2A120.0C18—C17—C16120.1 (3)
C19—N2—H2B120.0C18—C17—H17120.0
H2A—N2—H2B120.0C16—C17—H17120.0
C24—N3—C20118.3 (2)C17—C18—C19119.7 (3)
C24—N3—Zn1126.28 (18)C17—C18—H18120.1
C20—N3—Zn1115.39 (17)C19—C18—H18120.1
C24—N4—H4A120.0N2—C19—N1118.8 (2)
C24—N4—H4B120.0N2—C19—C18120.9 (2)
H4A—N4—H4B120.0N1—C19—C18120.2 (3)
O1—C1—O2122.0 (3)N3—C20—C21123.6 (3)
O1—C1—C2121.0 (3)N3—C20—H20118.2
O2—C1—C2117.0 (2)C21—C20—H20118.2
C3—C2—C7118.2 (3)C20—C21—C22117.9 (3)
C3—C2—C1119.7 (3)C20—C21—H21121.1
C7—C2—C1122.0 (2)C22—C21—H21121.1
C5—C4—C3119.7 (4)C23—C22—C21119.8 (3)
C5—C4—H4120.2C23—C22—H22120.1
C3—C4—H4120.2C21—C22—H22120.1
C6—C5—C4122.3 (4)C22—C23—C24120.3 (3)
C6—C5—H5118.9C22—C23—H23119.9
C4—C5—H5118.9C24—C23—H23119.9
C5—C6—C7119.9 (5)N4—C24—N3118.9 (2)
C5—C6—H6120.0N4—C24—C23121.0 (3)
C7—C6—H6120.0N3—C24—C23120.2 (3)
O4—C8—O3121.6 (3)F1—C7—C6116.7 (4)
O4—C8—C9122.0 (3)F1—C7—C2122.0 (3)
O3—C8—C9116.3 (3)C6—C7—C2121.3 (3)
O4—C8—Zn174.24 (19)F2—C14—C9118.2 (3)
O3—C8—Zn147.44 (15)F2—C14—C13116.3 (4)
C9—C8—Zn1162.8 (2)C9—C14—C13125.0 (3)
C14—C9—C10114.0 (3)C2—C3—C4118.7 (4)
C14—C9—C8122.6 (3)C2—C3—H3120.7
C10—C9—C8123.4 (3)C4—C3—H3120.7
C12—C11—C10120.0 (4)C11—C10—C9122.8 (4)
C12—C11—H11120.0C11—C10—H10118.6
C10—C11—H11120.0C9—C10—H10118.6
C11—C12—C13120.1 (4)
O3—Zn1—O2—C151.6 (3)C15—C16—C17—C181.1 (5)
N3—Zn1—O2—C1177.40 (19)C16—C17—C18—C190.2 (5)
N1—Zn1—O2—C175.1 (2)C15—N1—C19—N2177.1 (2)
O2—Zn1—O3—C836.6 (3)Zn1—N1—C19—N210.8 (3)
N3—Zn1—O3—C890.4 (2)C15—N1—C19—C182.5 (3)
N1—Zn1—O3—C8162.48 (18)Zn1—N1—C19—C18169.68 (18)
O2—Zn1—N1—C19135.18 (19)C17—C18—C19—N2177.9 (3)
O3—Zn1—N1—C1910.5 (2)C17—C18—C19—N11.6 (4)
N3—Zn1—N1—C19116.0 (2)C24—N3—C20—C211.3 (4)
O2—Zn1—N1—C1537.2 (2)Zn1—N3—C20—C21179.9 (2)
O3—Zn1—N1—C15177.07 (19)N3—C20—C21—C221.4 (5)
N3—Zn1—N1—C1571.6 (2)C20—C21—C22—C230.6 (5)
O2—Zn1—N3—C244.3 (2)C21—C22—C23—C240.3 (5)
O3—Zn1—N3—C24150.1 (2)C20—N3—C24—N4179.2 (3)
N1—Zn1—N3—C24102.0 (2)Zn1—N3—C24—N42.1 (4)
O2—Zn1—N3—C20174.40 (19)C20—N3—C24—C230.4 (4)
O3—Zn1—N3—C2028.7 (2)Zn1—N3—C24—C23179.0 (2)
N1—Zn1—N3—C2079.3 (2)C22—C23—C24—N4178.4 (3)
Zn1—O2—C1—O11.2 (4)C22—C23—C24—N30.4 (4)
Zn1—O2—C1—C2179.48 (17)C5—C6—C7—F1177.9 (4)
O1—C1—C2—C30.8 (4)C5—C6—C7—C20.6 (6)
O2—C1—C2—C3179.9 (3)C3—C2—C7—F1178.0 (3)
O1—C1—C2—C7179.2 (3)C1—C2—C7—F10.4 (5)
O2—C1—C2—C71.5 (4)C3—C2—C7—C60.4 (5)
C3—C4—C5—C60.8 (7)C1—C2—C7—C6178.8 (3)
C4—C5—C6—C70.9 (7)C10—C9—C14—F2172.1 (4)
Zn1—O3—C8—O43.1 (4)C8—C9—C14—F210.5 (5)
Zn1—O3—C8—C9173.20 (19)C10—C9—C14—C130.1 (5)
O4—C8—C9—C1434.1 (5)C8—C9—C14—C13177.5 (3)
O3—C8—C9—C14149.6 (3)C12—C13—C14—F2175.0 (5)
O4—C8—C9—C10143.0 (4)C12—C13—C14—C92.9 (6)
O3—C8—C9—C1033.3 (4)C7—C2—C3—C40.4 (4)
C10—C11—C12—C132.6 (7)C1—C2—C3—C4178.8 (3)
C11—C12—C13—C144.1 (7)C5—C4—C3—C20.6 (6)
C19—N1—C15—C161.6 (4)C12—C11—C10—C90.3 (7)
Zn1—N1—C15—C16171.6 (3)C14—C9—C10—C111.6 (5)
N1—C15—C16—C170.2 (5)C8—C9—C10—C11175.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.062.883 (3)159
N2—H2B···O1i0.862.032.863 (3)163
N4—H4A···F10.862.533.159 (4)131
N4—H4A···O20.862.012.837 (3)160
N4—H4B···O4ii0.862.032.886 (3)175
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+3/2, y1/2, z+3/2.
 

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