Bis{N-[(1Z,3Z)-1,3-bis­(4-fluoro­phen­yl)-3-(phenyl­imino)prop-1-en­yl]aniline(1–)}­zinc(II)

Peng, Y.-L.; Hsueh, M.-L.; Lin, C.-C.

doi:10.1107/S1600536807040123

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Bis{N-[(1Z,3Z)-1,3-bis(4-fluorophenyl)-3-(phenylimino)prop-1-enyl]aniline(1-)}zinc(II)

Y.-L. Peng, M.-L. Hsueh and C.-C. Lin

In the title complex, [Zn(C₂₇H₁₉F₂N₂)₂], a twofold rotation axis passes through the Zn atom, which is tetrahedrally coordinated by four N atoms from two diketiminate ligands. There are no intermolecular interactions of note in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040123/gg2033sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040123/gg2033Isup2.hkl Contains datablock I

CCDC reference: 660143

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.105
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.524     1.000
            Tmin(prime) and Tmax expected:      0.727     0.916
            RR(prime) =      0.660
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.66

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C54 H38 F4 N4 Zn

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.916
            Tmax scaled      0.916 Tmin scaled      0.480
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.92

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Biodegradable polymers have been attracting considerable attention recently due to their potential applications in the environmental protection as well as in the medical field. Among biodegradable polymers, the aliphatic polyesters, such as poly(ε-caprolactone) (PCL), (Endo et al., 1987) poly(lactide) (PLA) (Chamberlain et al., 1999), and their copolymers are especially interested for their applications in the medical field as biodegradable surgical sutures or as a delivery medium for controlled release of drugs (Ni & Yu, 1997). Therefore, there has been increasing interest in the development of efficient catalytic systems for the preparation of PLA and PCL (Wu et al., 2006). The major polymerization method used to synthesize these polymers has been the ring-opening polymerization (ROP) of lactones/lactides and functionally related compounds. For examples, aluminium alkoxides (Duda et al., 1990), stannous (Sawhney et al., 1993), yttrium (Stevels et al., 1996) as well as trivalent lanthanide derivatives (Simic et al., 1997), lithium (Ko & Lin, 2001), magnesium (Shueh et al., 2004; Chamberlain et al., 2001), calcium (Chisholm et al., 2003) and zinc (Chamberlain et al., 2001; Rieth et al., 2002) have been reported to be effective initiators that initiate ROP of lactones/lactides, yielding polymers with both high molecular weights and high yields. Among them, zinc diketiminato-based catalytic systems are especially attracted and well suited as initiators for the ROP of lactones and lactides due to their high Lewis acidity. Recently, we have reported that Zn complexes of diketiminato-based ligands are very active catalysts for ROP of lactide (Chen et al., 2005). Herein, we report the crystal structure of a potentially useful Zn complex with bulky diketiminato ligands.

In the title mononuclear Zn^II compound, the Zn atom is tetracoordinated with four N atoms from two diketiminato ligands (Fig. 1). The Zn atom lies on a C₂ rotation symmetry. By comparison with the Zn complexes reported in the literature, we notice that the Zn—N coordinated bond distances (1.989 (2) and 1.994 (2) Å)(Table 1) of the title compound are consistent with that reported for [(BDI-2)Zn(µ–OiPr)]₂ (1.990 (8) and 2.021 (7) Å) (Chamberlain et al., 2001).

Related literature top

For related literature, see: Chamberlain et al. (1999, 2001); Chen et al. (2005); Chisholm et al. (2003); Duda et al. (1990); Endo et al. (1987); Ko & Lin (2001); Rieth et al. (2002); Sawhney et al. (1993); Shueh et al. (2004); Simic et al. (1997); Stevels et al. (1996); Wu et al. (2006).

For related literature, see: Ni & Yu (1997 or??? 1998).

Experimental top

The title compound was prepared by the reaction of N-((1Z,3Z)-1,3-bis(4-fluorophenyl)-3-(phenylimino)prop-1- enyl)benzenamine (0.82 g, 2.0 mmol) with ZnEt₂ (1.1 ml, 1.0 M in hexane, 1.1 mmol) in hexane (20 ml). The mixture was stirred at 25°C for 6 h and was then evaporated to dryness under vacuum. The residue was extracted with hot hexane (30 ml), and the resulting hexane solution was then concentrated to ca 15 ml. Yellow crystals were obtained at room temperature after 16 h. Yield: 0.61 g (69%).

Structure description top

For related literature, see: Ni & Yu (1997 or??? 1998).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

Fig. 1. A view of the molecular structure of (I) with displacement ellipsoids shown at the 20% probability level. All the H atoms are omitted for clarity.

Bis{N-[(1Z,3Z)-1,3-bis(4-fluorophenyl)-3- (phenylimino)prop-1-enyl]aniline(1-)}zinc(II) top

Crystal data top

[Zn(C₂₇H₁₉F₂N₂)₂]	F(000) = 1824
M_r = 884.26	D_x = 1.358 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3748 reflections
a = 21.967 (2) Å	θ = 2.5–25.5°
b = 10.6232 (10) Å	µ = 0.63 mm⁻¹
c = 19.2852 (19) Å	T = 298 K
β = 106.102 (2)°	Parallelpiped, yellow
V = 4323.8 (7) Å³	0.50 × 0.25 × 0.14 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	4272 independent reflections
Radiation source: fine-focus sealed tube	3043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
φ and ω scans	θ_max = 26.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −27→24
T_min = 0.524, T_max = 1.000	k = −13→11
12028 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
4272 reflections	(Δ/σ)_max = 0.001
285 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Zn(C₂₇H₁₉F₂N₂)₂]	V = 4323.8 (7) Å³
M_r = 884.26	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.967 (2) Å	µ = 0.63 mm⁻¹
b = 10.6232 (10) Å	T = 298 K
c = 19.2852 (19) Å	0.50 × 0.25 × 0.14 mm
β = 106.102 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4272 independent reflections
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	3043 reflections with I > 2σ(I)
T_min = 0.524, T_max = 1.000	R_int = 0.048
12028 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 0.95	Δρ_max = 0.36 e Å⁻³
4272 reflections	Δρ_min = −0.30 e Å⁻³
285 parameters

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

	x	y	z	U_iso*/U_eq
Zn	0.5000	0.15528 (4)	1.2500	0.03975 (14)
F1	0.72953 (9)	0.0113 (2)	0.97921 (11)	0.0977 (7)
F2	0.33272 (10)	0.65322 (18)	0.92235 (10)	0.0936 (6)
N1	0.54684 (9)	0.06780 (18)	1.18950 (9)	0.0403 (5)
N2	0.44306 (9)	0.25386 (19)	1.16987 (9)	0.0424 (5)
C1	0.55117 (11)	0.1220 (2)	1.12847 (11)	0.0391 (5)
C2	0.51558 (11)	0.2276 (2)	1.09706 (11)	0.0428 (6)
H2A	0.5292	0.2669	1.0609	0.051*
C3	0.46282 (11)	0.2823 (2)	1.11195 (11)	0.0412 (5)
C4	0.57425 (12)	−0.0522 (2)	1.21246 (12)	0.0429 (6)
C5	0.62314 (13)	−0.0624 (3)	1.27565 (13)	0.0550 (7)
H5A	0.6406	0.0097	1.3008	0.066*
C6	0.64604 (16)	−0.1804 (3)	1.30144 (15)	0.0682 (9)
H6A	0.6791	−0.1869	1.3436	0.082*
C7	0.62031 (17)	−0.2870 (3)	1.26521 (18)	0.0714 (9)
H7A	0.6355	−0.3658	1.2828	0.086*
C8	0.57228 (17)	−0.2772 (3)	1.20321 (18)	0.0709 (9)
H8A	0.5551	−0.3497	1.1784	0.085*
C9	0.54883 (15)	−0.1610 (3)	1.17676 (15)	0.0587 (7)
H9A	0.5157	−0.1559	1.1346	0.070*
C10	0.59870 (11)	0.0783 (2)	1.09063 (12)	0.0401 (5)
C11	0.66212 (12)	0.0696 (2)	1.12655 (13)	0.0495 (6)
H11A	0.6753	0.0790	1.1764	0.059*
C12	0.70666 (13)	0.0471 (3)	1.08923 (16)	0.0581 (7)
H12A	0.7495	0.0419	1.1135	0.070*
C13	0.68610 (14)	0.0326 (3)	1.01600 (16)	0.0596 (7)
C14	0.62417 (15)	0.0373 (3)	0.97884 (14)	0.0583 (7)
H14A	0.6115	0.0241	0.9292	0.070*
C15	0.57990 (12)	0.0620 (3)	1.01597 (12)	0.0486 (6)
H15A	0.5372	0.0678	0.9909	0.058*
C16	0.42858 (11)	0.3809 (2)	1.06036 (12)	0.0411 (6)
C17	0.41609 (13)	0.4975 (2)	1.08620 (14)	0.0534 (7)
H17A	0.4291	0.5132	1.1356	0.064*
C18	0.38494 (15)	0.5900 (3)	1.04009 (16)	0.0625 (8)
H18A	0.3771	0.6682	1.0576	0.075*
C19	0.36572 (14)	0.5641 (3)	0.96792 (16)	0.0629 (8)
C20	0.37753 (14)	0.4522 (3)	0.93986 (14)	0.0633 (8)
H20A	0.3641	0.4377	0.8904	0.076*
C21	0.40987 (13)	0.3606 (3)	0.98648 (13)	0.0540 (7)
H21A	0.4192	0.2844	0.9681	0.065*
C22	0.37975 (12)	0.2775 (2)	1.17125 (12)	0.0434 (6)
C23	0.36800 (14)	0.3224 (3)	1.23379 (14)	0.0563 (7)
H23A	0.4014	0.3478	1.2725	0.068*
C24	0.30590 (17)	0.3294 (3)	1.23820 (17)	0.0731 (10)
H24A	0.2982	0.3601	1.2801	0.088*
C25	0.25627 (16)	0.2920 (3)	1.1824 (2)	0.0775 (10)
H25A	0.2151	0.2958	1.1866	0.093*
C26	0.26751 (14)	0.2485 (3)	1.11993 (17)	0.0688 (8)
H26A	0.2338	0.2239	1.0813	0.083*
C27	0.32846 (12)	0.2416 (2)	1.11452 (14)	0.0513 (6)
H27A	0.3355	0.2123	1.0720	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0429 (2)	0.0499 (3)	0.0307 (2)	0.000	0.01727 (16)	0.000
F1	0.0807 (14)	0.1299 (18)	0.1090 (14)	0.0018 (12)	0.0703 (12)	−0.0228 (13)
F2	0.1059 (16)	0.0791 (13)	0.0928 (13)	0.0291 (11)	0.0227 (12)	0.0447 (11)
N1	0.0457 (12)	0.0467 (11)	0.0319 (9)	0.0068 (9)	0.0167 (8)	0.0036 (9)
N2	0.0427 (12)	0.0517 (12)	0.0372 (10)	0.0062 (9)	0.0182 (9)	0.0043 (9)
C1	0.0383 (13)	0.0491 (14)	0.0323 (11)	0.0012 (10)	0.0138 (10)	0.0006 (10)
C2	0.0458 (15)	0.0536 (15)	0.0345 (11)	0.0054 (11)	0.0202 (10)	0.0083 (11)
C3	0.0437 (14)	0.0472 (14)	0.0349 (11)	0.0016 (11)	0.0144 (10)	0.0003 (11)
C4	0.0498 (15)	0.0502 (15)	0.0354 (11)	0.0061 (12)	0.0231 (11)	0.0050 (11)
C5	0.0649 (19)	0.0583 (17)	0.0425 (13)	0.0105 (14)	0.0163 (13)	0.0038 (12)
C6	0.082 (2)	0.074 (2)	0.0500 (16)	0.0247 (17)	0.0200 (15)	0.0170 (15)
C7	0.097 (3)	0.0561 (19)	0.074 (2)	0.0246 (18)	0.0461 (19)	0.0225 (17)
C8	0.094 (3)	0.0479 (18)	0.081 (2)	−0.0023 (16)	0.041 (2)	−0.0005 (16)
C9	0.0685 (19)	0.0552 (17)	0.0527 (15)	−0.0006 (15)	0.0174 (13)	−0.0014 (14)
C10	0.0419 (14)	0.0427 (13)	0.0406 (12)	0.0028 (10)	0.0196 (11)	0.0040 (10)
C11	0.0504 (17)	0.0556 (16)	0.0461 (13)	0.0068 (12)	0.0195 (12)	0.0024 (12)
C12	0.0415 (16)	0.0621 (18)	0.0756 (18)	0.0077 (13)	0.0247 (14)	0.0039 (15)
C13	0.0573 (19)	0.0666 (19)	0.0701 (18)	0.0022 (14)	0.0431 (15)	−0.0042 (15)
C14	0.071 (2)	0.0680 (18)	0.0461 (14)	−0.0005 (15)	0.0338 (14)	−0.0049 (13)
C15	0.0453 (15)	0.0631 (17)	0.0417 (12)	−0.0008 (12)	0.0190 (11)	−0.0033 (12)
C16	0.0411 (14)	0.0450 (14)	0.0416 (12)	0.0035 (10)	0.0186 (11)	0.0039 (10)
C17	0.0628 (18)	0.0510 (17)	0.0505 (14)	0.0008 (13)	0.0226 (13)	0.0026 (12)
C18	0.077 (2)	0.0423 (16)	0.0741 (19)	0.0078 (14)	0.0312 (16)	0.0065 (15)
C19	0.0630 (19)	0.0569 (18)	0.0716 (19)	0.0122 (14)	0.0232 (15)	0.0256 (15)
C20	0.070 (2)	0.075 (2)	0.0444 (14)	0.0102 (16)	0.0153 (13)	0.0124 (14)
C21	0.0635 (18)	0.0565 (16)	0.0446 (13)	0.0094 (13)	0.0191 (12)	0.0041 (12)
C22	0.0463 (15)	0.0452 (14)	0.0443 (13)	0.0088 (11)	0.0219 (11)	0.0082 (11)
C23	0.0637 (18)	0.0658 (19)	0.0468 (14)	0.0173 (14)	0.0274 (13)	0.0049 (13)
C24	0.084 (2)	0.087 (2)	0.0666 (19)	0.0328 (19)	0.0501 (18)	0.0177 (17)
C25	0.059 (2)	0.092 (2)	0.096 (2)	0.0266 (18)	0.047 (2)	0.029 (2)
C26	0.0512 (19)	0.075 (2)	0.081 (2)	0.0045 (15)	0.0209 (16)	0.0123 (17)
C27	0.0484 (16)	0.0565 (16)	0.0531 (15)	0.0051 (13)	0.0207 (13)	0.0034 (13)

Geometric parameters (Å, º) top

Zn—N1ⁱ	1.9875 (18)	C11—H11A	0.9300
Zn—N1	1.9875 (18)	C12—C13	1.367 (4)
Zn—N2ⁱ	1.9942 (19)	C12—H12A	0.9300
Zn—N2	1.9942 (19)	C13—C14	1.351 (4)
F1—C13	1.356 (3)	C14—C15	1.383 (3)
F2—C19	1.356 (3)	C14—H14A	0.9300
N1—C1	1.337 (3)	C15—H15A	0.9300
N1—C4	1.427 (3)	C16—C21	1.386 (3)
N2—C3	1.340 (3)	C16—C17	1.391 (3)
N2—C22	1.421 (3)	C17—C18	1.374 (4)
C1—C2	1.405 (3)	C17—H17A	0.9300
C1—C10	1.503 (3)	C18—C19	1.366 (4)
C2—C3	1.396 (3)	C18—H18A	0.9300
C2—H2A	0.9300	C19—C20	1.361 (4)
C3—C16	1.496 (3)	C20—C21	1.380 (4)
C4—C9	1.382 (4)	C20—H20A	0.9300
C4—C5	1.387 (3)	C21—H21A	0.9300
C5—C6	1.390 (4)	C22—C27	1.389 (4)
C5—H5A	0.9300	C22—C23	1.386 (3)
C6—C7	1.368 (4)	C23—C24	1.392 (4)
C6—H6A	0.9300	C23—H23A	0.9300
C7—C8	1.362 (4)	C24—C25	1.361 (5)
C7—H7A	0.9300	C24—H24A	0.9300
C8—C9	1.379 (4)	C25—C26	1.376 (4)
C8—H8A	0.9300	C25—H25A	0.9300
C9—H9A	0.9300	C26—C27	1.374 (4)
C10—C11	1.376 (3)	C26—H26A	0.9300
C10—C15	1.394 (3)	C27—H27A	0.9300
C11—C12	1.387 (3)

N1ⁱ—Zn—N1	124.24 (11)	C11—C12—H12A	120.7
N1ⁱ—Zn—N2ⁱ	96.10 (7)	C14—C13—F1	118.6 (3)
N1—Zn—N2ⁱ	112.64 (8)	C14—C13—C12	122.6 (2)
N1ⁱ—Zn—N2	112.64 (8)	F1—C13—C12	118.7 (3)
N1—Zn—N2	96.10 (7)	C13—C14—C15	118.8 (2)
N2ⁱ—Zn—N2	116.65 (12)	C13—C14—H14A	120.6
C1—N1—C4	122.07 (19)	C15—C14—H14A	120.6
C1—N1—Zn	119.36 (16)	C14—C15—C10	120.6 (2)
C4—N1—Zn	118.57 (13)	C14—C15—H15A	119.7
C3—N2—C22	121.39 (19)	C10—C15—H15A	119.7
C3—N2—Zn	119.06 (16)	C21—C16—C17	118.4 (2)
C22—N2—Zn	119.01 (14)	C21—C16—C3	121.7 (2)
N1—C1—C2	123.8 (2)	C17—C16—C3	119.9 (2)
N1—C1—C10	121.5 (2)	C18—C17—C16	121.2 (2)
C2—C1—C10	114.56 (19)	C18—C17—H17A	119.4
C3—C2—C1	129.7 (2)	C16—C17—H17A	119.4
C3—C2—H2A	115.2	C19—C18—C17	118.3 (3)
C1—C2—H2A	115.2	C19—C18—H18A	120.9
N2—C3—C2	123.8 (2)	C17—C18—H18A	120.9
N2—C3—C16	119.5 (2)	F2—C19—C20	118.6 (3)
C2—C3—C16	116.61 (19)	F2—C19—C18	118.6 (3)
C9—C4—C5	118.7 (2)	C20—C19—C18	122.8 (3)
C9—C4—N1	121.0 (2)	C19—C20—C21	118.5 (3)
C5—C4—N1	120.0 (2)	C19—C20—H20A	120.7
C4—C5—C6	120.0 (3)	C21—C20—H20A	120.7
C4—C5—H5A	120.0	C20—C21—C16	120.8 (3)
C6—C5—H5A	120.0	C20—C21—H21A	119.6
C7—C6—C5	120.4 (3)	C16—C21—H21A	119.6
C7—C6—H6A	119.8	C27—C22—C23	118.3 (2)
C5—C6—H6A	119.8	C27—C22—N2	121.4 (2)
C8—C7—C6	119.6 (3)	C23—C22—N2	119.8 (2)
C8—C7—H7A	120.2	C22—C23—C24	119.6 (3)
C6—C7—H7A	120.2	C22—C23—H23A	120.2
C7—C8—C9	120.8 (3)	C24—C23—H23A	120.2
C7—C8—H8A	119.6	C25—C24—C23	121.4 (3)
C9—C8—H8A	119.6	C25—C24—H24A	119.3
C8—C9—C4	120.4 (3)	C23—C24—H24A	119.3
C8—C9—H9A	119.8	C24—C25—C26	119.4 (3)
C4—C9—H9A	119.8	C24—C25—H25A	120.3
C11—C10—C15	118.7 (2)	C26—C25—H25A	120.3
C11—C10—C1	121.2 (2)	C27—C26—C25	120.0 (3)
C15—C10—C1	119.5 (2)	C27—C26—H26A	120.0
C10—C11—C12	120.8 (2)	C25—C26—H26A	120.0
C10—C11—H11A	119.6	C26—C27—C22	121.4 (3)
C12—C11—H11A	119.6	C26—C27—H27A	119.3
C13—C12—C11	118.5 (3)	C22—C27—H27A	119.3
C13—C12—H12A	120.7

Symmetry code: (i) −x+1, y, −z+5/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₂₇H₁₉F₂N₂)₂]
M_r	884.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	21.967 (2), 10.6232 (10), 19.2852 (19)
β (°)	106.102 (2)
V (Å³)	4323.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.50 × 0.25 × 0.14

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS, Sheldrick, 1996)
T_min, T_max	0.524, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12028, 4272, 3043
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 0.95
No. of reflections	4272
No. of parameters	285
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

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