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In the title compound, [ZnII(Cl)2(C17H23N3O2)] or [ZnII(Cl)2(pybox)], where pybox is 2,6-bis­[(4R)-(+)-4-iso­propyl-4,5-di­hydro-1,3-oxazol-2-yl]­pyridine, the coordination geometry is a distorted trigonal bipyramid. The pybox exhibits tridentate coordination to ZnII in a [1:1] ratio, with the apical positions of the bipyramid occupied by the oxazoline N atoms of the ligand. The two Cl atoms and the pyridine N atom form the trigonal base of the bipyramid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301924X/bt6337sup1.cif
Contains datablocks k0248, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301924X/bt6337Isup2.hkl
Contains datablock I

CCDC reference: 225657

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.031
  • wR factor = 0.080
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N1 = 5.49 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - N3 = 8.63 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.60 From the CIF: _reflns_number_total 3959 Count of symmetry unique reflns 2230 Completeness (_total/calc) 177.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1729 Fraction of Friedel pairs measured 0.775 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Zn(C17H23N3O2)Cl2]Z = 1
Mr = 437.65F(000) = 226
Triclinic, P1Dx = 1.509 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4392 (1) ÅCell parameters from 10216 reflections
b = 8.4408 (1) Åθ = 2.6–27.5°
c = 8.7411 (2) ŵ = 1.57 mm1
α = 113.027 (1)°T = 150 K
β = 97.040 (1)°Needle, colourless
γ = 101.818 (1)°0.46 × 0.16 × 0.14 mm
V = 481.76 (2) Å3
Data collection top
Nonius KappaCCD
diffractometer
3959 independent reflections
Radiation source: fine-focus sealed tube3899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 9 pixels mm-1θmax = 27.6°, θmin = 2.6°
φ scans and ω scans with κ offsetsh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1010
Tmin = 0.710, Tmax = 0.800l = 1111
7172 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031 w = 1/[σ2(Fo2) + (0.0387P)2 + 0.1173P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.47 e Å3
3959 reflectionsΔρmin = 0.54 e Å3
227 parametersExtinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.035 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983); 1455 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.006 (7)
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
Zn10.337340 (11)0.122450 (11)0.348882 (11)0.02054 (10)
Cl10.15455 (8)0.11054 (9)0.12005 (8)0.02249 (14)
Cl20.55429 (9)0.37385 (9)0.53087 (9)0.02754 (16)
O10.6337 (3)0.2783 (3)0.1869 (3)0.0237 (4)
O20.0898 (3)0.0270 (3)0.6062 (3)0.0263 (4)
N10.5329 (3)0.0340 (3)0.2195 (3)0.0194 (4)
N20.2726 (3)0.1169 (3)0.3814 (3)0.0183 (4)
N30.0991 (3)0.1369 (3)0.5054 (3)0.0187 (4)
C10.6969 (4)0.0142 (4)0.1396 (4)0.0215 (5)
H1A0.80530.08290.22800.026*
C20.7427 (4)0.1959 (4)0.0946 (4)0.0256 (6)
H2A0.70370.27180.02990.031*
H2B0.87930.17760.13270.031*
C30.5160 (3)0.1771 (3)0.2397 (3)0.0189 (5)
C40.3680 (4)0.2384 (3)0.3182 (3)0.0183 (5)
C50.3230 (4)0.4043 (4)0.3220 (3)0.0239 (6)
H5A0.39450.48680.27990.029*
C60.1706 (4)0.4461 (4)0.3890 (4)0.0271 (6)
H6A0.13420.56020.39020.033*
C70.0701 (4)0.3223 (4)0.4547 (4)0.0263 (6)
H7A0.03460.34920.50150.032*
C80.1288 (4)0.1579 (4)0.4491 (3)0.0197 (5)
C90.0443 (3)0.0084 (3)0.5199 (3)0.0187 (5)
C100.1371 (4)0.1446 (4)0.6660 (4)0.0269 (6)
H10A0.11760.20030.79180.032*
H10B0.27000.12750.61500.032*
C110.0018 (4)0.2615 (4)0.6067 (4)0.0192 (5)
H11A0.07650.29940.53080.023*
C120.6590 (4)0.0310 (4)0.0121 (3)0.0228 (5)
H12A0.76830.01940.06770.027*
C130.6550 (4)0.2270 (4)0.0504 (4)0.0298 (6)
H13A0.63040.25470.04780.045*
H13B0.77690.30560.12550.045*
H13C0.55520.24600.11340.045*
C140.4822 (5)0.0943 (5)0.1479 (4)0.0324 (7)
H14A0.48810.21840.18540.049*
H14B0.47410.06410.24550.049*
H14C0.37080.08090.10010.049*
C150.1397 (4)0.4270 (4)0.7513 (3)0.0233 (5)
H15A0.21990.49080.69770.028*
C160.0369 (5)0.5558 (4)0.8570 (4)0.0335 (7)
H16A0.12930.66070.94880.050*
H16B0.04850.49480.90630.050*
H16C0.03590.59420.78350.050*
C170.2697 (5)0.3769 (5)0.8622 (4)0.0344 (7)
H17A0.33300.29480.79050.052*
H17B0.19570.31820.92030.052*
H17C0.36420.48530.94720.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02111 (15)0.01538 (14)0.02575 (16)0.00556 (10)0.00407 (10)0.00955 (11)
Cl10.0189 (3)0.0264 (3)0.0251 (3)0.0074 (2)0.0059 (2)0.0132 (3)
Cl20.0210 (3)0.0202 (3)0.0343 (3)0.0044 (2)0.0026 (2)0.0062 (3)
O10.0257 (9)0.0217 (10)0.0292 (10)0.0134 (8)0.0128 (8)0.0113 (8)
O20.0324 (10)0.0185 (9)0.0354 (11)0.0105 (8)0.0227 (9)0.0127 (8)
N10.0206 (10)0.0185 (10)0.0218 (10)0.0076 (8)0.0091 (8)0.0092 (8)
N20.0228 (10)0.0162 (10)0.0180 (10)0.0075 (8)0.0071 (8)0.0076 (8)
N30.0222 (9)0.0158 (10)0.0195 (10)0.0077 (8)0.0091 (8)0.0063 (8)
C10.0185 (12)0.0235 (14)0.0236 (13)0.0073 (10)0.0083 (10)0.0096 (11)
C20.0246 (12)0.0288 (15)0.0300 (14)0.0130 (11)0.0138 (11)0.0143 (12)
C30.0193 (11)0.0183 (12)0.0192 (11)0.0092 (10)0.0050 (9)0.0059 (10)
C40.0232 (11)0.0148 (11)0.0181 (11)0.0067 (9)0.0056 (9)0.0072 (9)
C50.0339 (14)0.0182 (14)0.0230 (14)0.0124 (12)0.0100 (11)0.0087 (11)
C60.0408 (16)0.0172 (12)0.0296 (14)0.0114 (12)0.0147 (12)0.0128 (11)
C70.0328 (14)0.0223 (14)0.0280 (13)0.0080 (11)0.0141 (11)0.0128 (11)
C80.0249 (12)0.0171 (12)0.0200 (11)0.0065 (10)0.0095 (10)0.0093 (9)
C90.0200 (11)0.0183 (12)0.0184 (11)0.0052 (10)0.0082 (9)0.0074 (10)
C100.0288 (14)0.0196 (13)0.0356 (14)0.0096 (11)0.0184 (12)0.0106 (11)
C110.0220 (12)0.0163 (13)0.0216 (13)0.0081 (10)0.0105 (10)0.0075 (10)
C120.0183 (12)0.0270 (14)0.0250 (12)0.0066 (10)0.0093 (10)0.0118 (11)
C130.0271 (14)0.0316 (16)0.0385 (16)0.0103 (12)0.0133 (12)0.0201 (14)
C140.0279 (14)0.0373 (19)0.0265 (15)0.0046 (13)0.0051 (12)0.0107 (14)
C150.0265 (13)0.0214 (13)0.0210 (12)0.0066 (11)0.0078 (10)0.0074 (11)
C160.0411 (16)0.0223 (14)0.0327 (15)0.0096 (12)0.0156 (13)0.0048 (12)
C170.0403 (17)0.0353 (18)0.0230 (14)0.0132 (15)0.0014 (12)0.0083 (13)
Geometric parameters (Å, º) top
Zn1—N22.117 (2)C7—C81.389 (4)
Zn1—Cl22.2283 (7)C7—H7A0.9500
Zn1—Cl12.2316 (6)C8—C91.477 (4)
Zn1—N12.271 (2)C10—C111.542 (4)
Zn1—N32.362 (2)C10—H10A0.9900
O1—C31.344 (3)C10—H10B0.9900
O1—C21.470 (3)C11—C151.532 (4)
O2—C91.343 (3)C11—H11A1.0000
O2—C101.468 (3)C12—C141.524 (4)
N1—C31.272 (4)C12—C131.534 (4)
N1—C11.491 (3)C12—H12A1.0000
N2—C81.333 (3)C13—H13A0.9800
N2—C41.346 (3)C13—H13B0.9800
N3—C91.271 (4)C13—H13C0.9800
N3—C111.487 (3)C14—H14A0.9800
C1—C121.527 (4)C14—H14B0.9800
C1—C21.549 (4)C14—H14C0.9800
C1—H1A1.0000C15—C171.521 (4)
C2—H2A0.9900C15—C161.532 (4)
C2—H2B0.9900C15—H15A1.0000
C3—C41.477 (4)C16—H16A0.9800
C4—C51.386 (4)C16—H16B0.9800
C5—C61.383 (4)C16—H16C0.9800
C5—H5A0.9500C17—H17A0.9800
C6—C71.392 (4)C17—H17B0.9800
C6—H6A0.9500C17—H17C0.9800
N2—Zn1—Cl2124.58 (6)N3—C9—O2120.0 (2)
N2—Zn1—Cl1114.03 (6)N3—C9—C8121.9 (2)
Cl2—Zn1—Cl1121.28 (3)O2—C9—C8118.1 (2)
N2—Zn1—N174.90 (9)O2—C10—C11104.9 (2)
Cl2—Zn1—N198.50 (6)O2—C10—H10A110.8
Cl1—Zn1—N199.43 (6)C11—C10—H10A110.8
N2—Zn1—N372.71 (8)O2—C10—H10B110.8
Cl2—Zn1—N399.09 (6)C11—C10—H10B110.8
Cl1—Zn1—N394.34 (6)H10A—C10—H10B108.8
N1—Zn1—N3147.60 (8)N3—C11—C15110.2 (2)
C3—O1—C2104.5 (2)N3—C11—C10103.3 (2)
C9—O2—C10104.8 (2)C15—C11—C10114.8 (2)
C3—N1—C1106.9 (2)N3—C11—H11A109.5
C3—N1—Zn1111.27 (17)C15—C11—H11A109.5
C1—N1—Zn1141.00 (19)C10—C11—H11A109.5
C8—N2—C4118.9 (2)C14—C12—C1114.3 (3)
C8—N2—Zn1121.74 (18)C14—C12—C13111.1 (3)
C4—N2—Zn1119.10 (18)C1—C12—C13110.1 (2)
C9—N3—C11106.7 (2)C14—C12—H12A107.0
C9—N3—Zn1110.62 (17)C1—C12—H12A107.0
C11—N3—Zn1142.42 (18)C13—C12—H12A107.0
N1—C1—C12114.0 (2)C12—C13—H13A109.5
N1—C1—C2102.5 (2)C12—C13—H13B109.5
C12—C1—C2114.2 (2)H13A—C13—H13B109.5
N1—C1—H1A108.6C12—C13—H13C109.5
C12—C1—H1A108.6H13A—C13—H13C109.5
C2—C1—H1A108.6H13B—C13—H13C109.5
O1—C2—C1104.5 (2)C12—C14—H14A109.5
O1—C2—H2A110.9C12—C14—H14B109.5
C1—C2—H2A110.9H14A—C14—H14B109.5
O1—C2—H2B110.9C12—C14—H14C109.5
C1—C2—H2B110.9H14A—C14—H14C109.5
H2A—C2—H2B108.9H14B—C14—H14C109.5
N1—C3—O1119.8 (2)C17—C15—C11111.9 (3)
N1—C3—C4121.9 (2)C17—C15—C16111.7 (2)
O1—C3—C4118.2 (2)C11—C15—C16110.5 (2)
N2—C4—C5122.3 (2)C17—C15—H15A107.5
N2—C4—C3112.4 (2)C11—C15—H15A107.5
C5—C4—C3125.2 (2)C16—C15—H15A107.5
C6—C5—C4117.9 (3)C15—C16—H16A109.5
C6—C5—H5A121.0C15—C16—H16B109.5
C4—C5—H5A121.0H16A—C16—H16B109.5
C5—C6—C7120.5 (3)C15—C16—H16C109.5
C5—C6—H6A119.7H16A—C16—H16C109.5
C7—C6—H6A119.7H16B—C16—H16C109.5
C8—C7—C6117.3 (3)C15—C17—H17A109.5
C8—C7—H7A121.3C15—C17—H17B109.5
C6—C7—H7A121.3H17A—C17—H17B109.5
N2—C8—C7123.0 (3)C15—C17—H17C109.5
N2—C8—C9112.5 (2)H17A—C17—H17C109.5
C7—C8—C9124.6 (2)H17B—C17—H17C109.5
 

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