{2,6-Bis­[(4R)-(+)-4-iso­propyl-4,5-di­hydro-1,3-oxazol-2-yl]­pyridine-κ³N}di­chloro­zinc(II)

In the title compound, [Zn^II(Cl)₂(C₁₇H₂₃N₃O₂)] or [Zn^II(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 Zn^II 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.

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

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Computing details

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)

Crystal data

[Zn(C17H23N3O2)Cl2]	Z = 1
Mr = 437.65	F(000) = 226
Triclinic, P1	Dx = 1.509 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4392 (1) Å	Cell parameters from 10216 reflections
b = 8.4408 (1) Å	θ = 2.6–27.5°
c = 8.7411 (2) Å	µ = 1.57 mm^−1
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) Å^3

Data collection

Nonius KappaCCD diffractometer	3959 independent reflections
Radiation source: fine-focus sealed tube	3899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 27.6°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
Tmin = 0.710, Tmax = 0.800	l = −11→11
7172 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0387P)^2 + 0.1173P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.47 e Å^−3
3959 reflections	Δρmin = −0.54 e Å^−3
227 parameters	Extinction correction: SHELXTL (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.035 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983); 1455 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.006 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.337340 (11)	0.122450 (11)	0.348882 (11)	0.02054 (10)
Cl1	0.15455 (8)	0.11054 (9)	0.12005 (8)	0.02249 (14)
Cl2	0.55429 (9)	0.37385 (9)	0.53087 (9)	0.02754 (16)
O1	0.6337 (3)	−0.2783 (3)	0.1869 (3)	0.0237 (4)
O2	−0.0898 (3)	−0.0270 (3)	0.6062 (3)	0.0263 (4)
N1	0.5329 (3)	−0.0340 (3)	0.2195 (3)	0.0194 (4)
N2	0.2726 (3)	−0.1169 (3)	0.3814 (3)	0.0183 (4)
N3	0.0991 (3)	0.1369 (3)	0.5054 (3)	0.0187 (4)
C1	0.6969 (4)	−0.0142 (4)	0.1396 (4)	0.0215 (5)
H1A	0.8053	0.0829	0.2280	0.026*
C2	0.7427 (4)	−0.1959 (4)	0.0946 (4)	0.0256 (6)
H2A	0.7037	−0.2718	−0.0299	0.031*
H2B	0.8793	−0.1776	0.1327	0.031*
C3	0.5160 (3)	−0.1771 (3)	0.2397 (3)	0.0189 (5)
C4	0.3680 (4)	−0.2384 (3)	0.3182 (3)	0.0183 (5)
C5	0.3230 (4)	−0.4043 (4)	0.3220 (3)	0.0239 (6)
H5A	0.3945	−0.4868	0.2799	0.029*
C6	0.1706 (4)	−0.4461 (4)	0.3890 (4)	0.0271 (6)
H6A	0.1342	−0.5602	0.3902	0.033*
C7	0.0701 (4)	−0.3223 (4)	0.4547 (4)	0.0263 (6)
H7A	−0.0346	−0.3492	0.5015	0.032*
C8	0.1288 (4)	−0.1579 (4)	0.4491 (3)	0.0197 (5)
C9	0.0443 (3)	−0.0084 (3)	0.5199 (3)	0.0187 (5)
C10	−0.1371 (4)	0.1446 (4)	0.6660 (4)	0.0269 (6)
H10A	−0.1176	0.2003	0.7918	0.032*
H10B	−0.2700	0.1275	0.6150	0.032*
C11	−0.0018 (4)	0.2615 (4)	0.6067 (4)	0.0192 (5)
H11A	−0.0765	0.2994	0.5308	0.023*
C12	0.6590 (4)	0.0310 (4)	−0.0121 (3)	0.0228 (5)
H12A	0.7683	0.0194	−0.0677	0.027*
C13	0.6550 (4)	0.2270 (4)	0.0504 (4)	0.0298 (6)
H13A	0.6304	0.2547	−0.0478	0.045*
H13B	0.7769	0.3056	0.1255	0.045*
H13C	0.5552	0.2460	0.1134	0.045*
C14	0.4822 (5)	−0.0943 (5)	−0.1479 (4)	0.0324 (7)
H14A	0.4881	−0.2184	−0.1854	0.049*
H14B	0.4741	−0.0641	−0.2455	0.049*
H14C	0.3708	−0.0809	−0.1001	0.049*
C15	0.1397 (4)	0.4270 (4)	0.7513 (3)	0.0233 (5)
H15A	0.2199	0.4908	0.6977	0.028*
C16	0.0369 (5)	0.5558 (4)	0.8570 (4)	0.0335 (7)
H16A	0.1293	0.6607	0.9488	0.050*
H16B	−0.0485	0.4948	0.9063	0.050*
H16C	−0.0359	0.5942	0.7835	0.050*
C17	0.2697 (5)	0.3769 (5)	0.8622 (4)	0.0344 (7)
H17A	0.3330	0.2948	0.7905	0.052*
H17B	0.1957	0.3182	0.9203	0.052*
H17C	0.3642	0.4853	0.9472	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02111 (15)	0.01538 (14)	0.02575 (16)	0.00556 (10)	0.00407 (10)	0.00955 (11)
Cl1	0.0189 (3)	0.0264 (3)	0.0251 (3)	0.0074 (2)	0.0059 (2)	0.0132 (3)
Cl2	0.0210 (3)	0.0202 (3)	0.0343 (3)	0.0044 (2)	0.0026 (2)	0.0062 (3)
O1	0.0257 (9)	0.0217 (10)	0.0292 (10)	0.0134 (8)	0.0128 (8)	0.0113 (8)
O2	0.0324 (10)	0.0185 (9)	0.0354 (11)	0.0105 (8)	0.0227 (9)	0.0127 (8)
N1	0.0206 (10)	0.0185 (10)	0.0218 (10)	0.0076 (8)	0.0091 (8)	0.0092 (8)
N2	0.0228 (10)	0.0162 (10)	0.0180 (10)	0.0075 (8)	0.0071 (8)	0.0076 (8)
N3	0.0222 (9)	0.0158 (10)	0.0195 (10)	0.0077 (8)	0.0091 (8)	0.0063 (8)
C1	0.0185 (12)	0.0235 (14)	0.0236 (13)	0.0073 (10)	0.0083 (10)	0.0096 (11)
C2	0.0246 (12)	0.0288 (15)	0.0300 (14)	0.0130 (11)	0.0138 (11)	0.0143 (12)
C3	0.0193 (11)	0.0183 (12)	0.0192 (11)	0.0092 (10)	0.0050 (9)	0.0059 (10)
C4	0.0232 (11)	0.0148 (11)	0.0181 (11)	0.0067 (9)	0.0056 (9)	0.0072 (9)
C5	0.0339 (14)	0.0182 (14)	0.0230 (14)	0.0124 (12)	0.0100 (11)	0.0087 (11)
C6	0.0408 (16)	0.0172 (12)	0.0296 (14)	0.0114 (12)	0.0147 (12)	0.0128 (11)
C7	0.0328 (14)	0.0223 (14)	0.0280 (13)	0.0080 (11)	0.0141 (11)	0.0128 (11)
C8	0.0249 (12)	0.0171 (12)	0.0200 (11)	0.0065 (10)	0.0095 (10)	0.0093 (9)
C9	0.0200 (11)	0.0183 (12)	0.0184 (11)	0.0052 (10)	0.0082 (9)	0.0074 (10)
C10	0.0288 (14)	0.0196 (13)	0.0356 (14)	0.0096 (11)	0.0184 (12)	0.0106 (11)
C11	0.0220 (12)	0.0163 (13)	0.0216 (13)	0.0081 (10)	0.0105 (10)	0.0075 (10)
C12	0.0183 (12)	0.0270 (14)	0.0250 (12)	0.0066 (10)	0.0093 (10)	0.0118 (11)
C13	0.0271 (14)	0.0316 (16)	0.0385 (16)	0.0103 (12)	0.0133 (12)	0.0201 (14)
C14	0.0279 (14)	0.0373 (19)	0.0265 (15)	0.0046 (13)	0.0051 (12)	0.0107 (14)
C15	0.0265 (13)	0.0214 (13)	0.0210 (12)	0.0066 (11)	0.0078 (10)	0.0074 (11)
C16	0.0411 (16)	0.0223 (14)	0.0327 (15)	0.0096 (12)	0.0156 (13)	0.0048 (12)
C17	0.0403 (17)	0.0353 (18)	0.0230 (14)	0.0132 (15)	0.0014 (12)	0.0083 (13)

Geometric parameters (Å, º)

Zn1—N2	2.117 (2)	C7—C8	1.389 (4)
Zn1—Cl2	2.2283 (7)	C7—H7A	0.9500
Zn1—Cl1	2.2316 (6)	C8—C9	1.477 (4)
Zn1—N1	2.271 (2)	C10—C11	1.542 (4)
Zn1—N3	2.362 (2)	C10—H10A	0.9900
O1—C3	1.344 (3)	C10—H10B	0.9900
O1—C2	1.470 (3)	C11—C15	1.532 (4)
O2—C9	1.343 (3)	C11—H11A	1.0000
O2—C10	1.468 (3)	C12—C14	1.524 (4)
N1—C3	1.272 (4)	C12—C13	1.534 (4)
N1—C1	1.491 (3)	C12—H12A	1.0000
N2—C8	1.333 (3)	C13—H13A	0.9800
N2—C4	1.346 (3)	C13—H13B	0.9800
N3—C9	1.271 (4)	C13—H13C	0.9800
N3—C11	1.487 (3)	C14—H14A	0.9800
C1—C12	1.527 (4)	C14—H14B	0.9800
C1—C2	1.549 (4)	C14—H14C	0.9800
C1—H1A	1.0000	C15—C17	1.521 (4)
C2—H2A	0.9900	C15—C16	1.532 (4)
C2—H2B	0.9900	C15—H15A	1.0000
C3—C4	1.477 (4)	C16—H16A	0.9800
C4—C5	1.386 (4)	C16—H16B	0.9800
C5—C6	1.383 (4)	C16—H16C	0.9800
C5—H5A	0.9500	C17—H17A	0.9800
C6—C7	1.392 (4)	C17—H17B	0.9800
C6—H6A	0.9500	C17—H17C	0.9800
N2—Zn1—Cl2	124.58 (6)	N3—C9—O2	120.0 (2)
N2—Zn1—Cl1	114.03 (6)	N3—C9—C8	121.9 (2)
Cl2—Zn1—Cl1	121.28 (3)	O2—C9—C8	118.1 (2)
N2—Zn1—N1	74.90 (9)	O2—C10—C11	104.9 (2)
Cl2—Zn1—N1	98.50 (6)	O2—C10—H10A	110.8
Cl1—Zn1—N1	99.43 (6)	C11—C10—H10A	110.8
N2—Zn1—N3	72.71 (8)	O2—C10—H10B	110.8
Cl2—Zn1—N3	99.09 (6)	C11—C10—H10B	110.8
Cl1—Zn1—N3	94.34 (6)	H10A—C10—H10B	108.8
N1—Zn1—N3	147.60 (8)	N3—C11—C15	110.2 (2)
C3—O1—C2	104.5 (2)	N3—C11—C10	103.3 (2)
C9—O2—C10	104.8 (2)	C15—C11—C10	114.8 (2)
C3—N1—C1	106.9 (2)	N3—C11—H11A	109.5
C3—N1—Zn1	111.27 (17)	C15—C11—H11A	109.5
C1—N1—Zn1	141.00 (19)	C10—C11—H11A	109.5
C8—N2—C4	118.9 (2)	C14—C12—C1	114.3 (3)
C8—N2—Zn1	121.74 (18)	C14—C12—C13	111.1 (3)
C4—N2—Zn1	119.10 (18)	C1—C12—C13	110.1 (2)
C9—N3—C11	106.7 (2)	C14—C12—H12A	107.0
C9—N3—Zn1	110.62 (17)	C1—C12—H12A	107.0
C11—N3—Zn1	142.42 (18)	C13—C12—H12A	107.0
N1—C1—C12	114.0 (2)	C12—C13—H13A	109.5
N1—C1—C2	102.5 (2)	C12—C13—H13B	109.5
C12—C1—C2	114.2 (2)	H13A—C13—H13B	109.5
N1—C1—H1A	108.6	C12—C13—H13C	109.5
C12—C1—H1A	108.6	H13A—C13—H13C	109.5
C2—C1—H1A	108.6	H13B—C13—H13C	109.5
O1—C2—C1	104.5 (2)	C12—C14—H14A	109.5
O1—C2—H2A	110.9	C12—C14—H14B	109.5
C1—C2—H2A	110.9	H14A—C14—H14B	109.5
O1—C2—H2B	110.9	C12—C14—H14C	109.5
C1—C2—H2B	110.9	H14A—C14—H14C	109.5
H2A—C2—H2B	108.9	H14B—C14—H14C	109.5
N1—C3—O1	119.8 (2)	C17—C15—C11	111.9 (3)
N1—C3—C4	121.9 (2)	C17—C15—C16	111.7 (2)
O1—C3—C4	118.2 (2)	C11—C15—C16	110.5 (2)
N2—C4—C5	122.3 (2)	C17—C15—H15A	107.5
N2—C4—C3	112.4 (2)	C11—C15—H15A	107.5
C5—C4—C3	125.2 (2)	C16—C15—H15A	107.5
C6—C5—C4	117.9 (3)	C15—C16—H16A	109.5
C6—C5—H5A	121.0	C15—C16—H16B	109.5
C4—C5—H5A	121.0	H16A—C16—H16B	109.5
C5—C6—C7	120.5 (3)	C15—C16—H16C	109.5
C5—C6—H6A	119.7	H16A—C16—H16C	109.5
C7—C6—H6A	119.7	H16B—C16—H16C	109.5
C8—C7—C6	117.3 (3)	C15—C17—H17A	109.5
C8—C7—H7A	121.3	C15—C17—H17B	109.5
C6—C7—H7A	121.3	H17A—C17—H17B	109.5
N2—C8—C7	123.0 (3)	C15—C17—H17C	109.5
N2—C8—C9	112.5 (2)	H17A—C17—H17C	109.5
C7—C8—C9	124.6 (2)	H17B—C17—H17C	109.5