Bis[(1Z,3Z)-1,3-bis­(4-fluoro­phen­yl)-N,N'-diphenyl­propane­diiminato]magnesium(II)

In the title complex, [Mg(C₂₇H₁₉F₂N₂)₂], the Mg^II atom, lying on a crystallographic twofold rotation axis, is tetrahedrally coordinated by four N atoms from two diiminate ligands.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.041
• wR factor = 0.113
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.

Bis[(1Z,3Z)-1,3-bis(4-fluorophenyl)-N,N'-diphenylpropanediiminato]magnesium(II)

Crystal data

[Mg(C27H19F2N2)2]	F(000) = 1752
Mr = 843.19	Dx = 1.287 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2674 reflections
a = 22.0564 (15) Å	θ = 2.3–22.9°
b = 10.5743 (7) Å	µ = 0.10 mm^−1
c = 19.4356 (13) Å	T = 298 K
β = 106.201 (1)°	Parallelepiped, yellow
V = 4353.0 (5) Å^3	0.37 × 0.34 × 0.26 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer	2339 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −27→27
12188 measured reflections	k = −13→10
4270 independent reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0567P)^2] where P = (Fo^2 + 2Fc^2)/3
4270 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

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
Mg	0.5000	0.15309 (9)	0.2500	0.0432 (3)
F1	0.33159 (8)	0.65235 (14)	−0.07840 (8)	0.1010 (5)
F2	0.72941 (7)	0.01347 (15)	−0.02150 (9)	0.1013 (6)
N1	0.44314 (7)	0.25070 (15)	0.16709 (8)	0.0464 (4)
N2	0.54626 (8)	0.06484 (15)	0.18583 (8)	0.0451 (4)
C1	0.46219 (9)	0.28050 (18)	0.10935 (10)	0.0445 (5)
C2	0.51500 (9)	0.22538 (19)	0.09460 (10)	0.0466 (5)
H2A	0.5284	0.2648	0.0586	0.056*
C3	0.55084 (9)	0.11980 (18)	0.12578 (10)	0.0422 (5)
C4	0.38015 (10)	0.27652 (19)	0.16888 (11)	0.0473 (5)
C5	0.32870 (10)	0.24184 (19)	0.11343 (12)	0.0552 (6)
H5A	0.3349	0.2125	0.0708	0.066*
C6	0.26824 (11)	0.2500 (2)	0.12012 (15)	0.0744 (7)
H6A	0.2341	0.2264	0.0821	0.089*
C7	0.25832 (14)	0.2927 (3)	0.18265 (18)	0.0858 (9)
H7A	0.2176	0.2971	0.1873	0.103*
C8	0.30860 (15)	0.3290 (2)	0.23819 (15)	0.0794 (8)
H8A	0.3018	0.3592	0.2804	0.095*
C9	0.36968 (12)	0.3210 (2)	0.23186 (12)	0.0628 (6)
H9A	0.4036	0.3454	0.2699	0.075*
C10	0.42826 (9)	0.37966 (19)	0.05840 (10)	0.0451 (5)
C11	0.40926 (10)	0.3594 (2)	−0.01487 (11)	0.0582 (6)
H11A	0.4186	0.2829	−0.0332	0.070*
C12	0.37675 (11)	0.4508 (2)	−0.06106 (13)	0.0677 (7)
H12A	0.3632	0.4363	−0.1102	0.081*
C13	0.36485 (11)	0.5632 (2)	−0.03289 (14)	0.0662 (7)
C14	0.38430 (12)	0.5893 (2)	0.03818 (14)	0.0674 (7)
H14A	0.3765	0.6678	0.0556	0.081*
C15	0.41584 (10)	0.4965 (2)	0.08377 (13)	0.0577 (6)
H15A	0.4291	0.5125	0.1327	0.069*
C16	0.59807 (9)	0.07764 (17)	0.08816 (10)	0.0424 (5)
C17	0.58006 (10)	0.06118 (19)	0.01429 (10)	0.0513 (5)
H17A	0.5375	0.0663	−0.0108	0.062*
C18	0.62418 (12)	0.0373 (2)	−0.02267 (12)	0.0614 (6)
H18A	0.6118	0.0246	−0.0720	0.074*
C19	0.68597 (12)	0.0331 (2)	0.01501 (14)	0.0624 (6)
C20	0.70626 (11)	0.0478 (2)	0.08743 (13)	0.0616 (6)
H20A	0.7490	0.0436	0.1115	0.074*
C21	0.66193 (10)	0.06915 (19)	0.12451 (11)	0.0520 (5)
H21A	0.6750	0.0779	0.1741	0.062*
C22	0.57449 (10)	−0.05449 (19)	0.20918 (11)	0.0472 (5)
C23	0.54983 (11)	−0.1652 (2)	0.17496 (12)	0.0631 (6)
H23A	0.5171	−0.1615	0.1328	0.076*
C24	0.57331 (14)	−0.2816 (2)	0.20272 (15)	0.0774 (8)
H24A	0.5565	−0.3554	0.1789	0.093*
C25	0.62108 (14)	−0.2885 (3)	0.26491 (15)	0.0773 (8)
H25A	0.6364	−0.3669	0.2837	0.093*
C26	0.64644 (13)	−0.1795 (3)	0.29959 (13)	0.0720 (7)
H26A	0.6795	−0.1841	0.3415	0.086*
C27	0.62290 (11)	−0.0626 (2)	0.27230 (12)	0.0610 (6)
H27A	0.6397	0.0108	0.2965	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg	0.0445 (6)	0.0547 (6)	0.0338 (5)	0.000	0.0164 (4)	0.000
F1	0.1136 (13)	0.0817 (11)	0.1039 (12)	0.0315 (9)	0.0241 (10)	0.0455 (9)
F2	0.0802 (11)	0.1323 (13)	0.1172 (13)	0.0020 (9)	0.0703 (11)	−0.0205 (10)
N1	0.0458 (10)	0.0580 (11)	0.0397 (9)	0.0055 (8)	0.0189 (8)	0.0016 (8)
N2	0.0510 (11)	0.0492 (10)	0.0390 (9)	0.0062 (8)	0.0188 (8)	0.0052 (8)
C1	0.0472 (13)	0.0486 (12)	0.0395 (11)	0.0008 (9)	0.0152 (10)	−0.0003 (9)
C2	0.0484 (13)	0.0557 (13)	0.0410 (11)	0.0078 (10)	0.0212 (10)	0.0091 (10)
C3	0.0397 (12)	0.0512 (12)	0.0389 (11)	0.0013 (9)	0.0161 (9)	−0.0010 (9)
C4	0.0495 (13)	0.0491 (12)	0.0493 (12)	0.0100 (10)	0.0233 (11)	0.0083 (10)
C5	0.0504 (14)	0.0579 (14)	0.0608 (14)	0.0053 (11)	0.0214 (12)	0.0028 (11)
C6	0.0540 (16)	0.0829 (19)	0.0902 (19)	0.0092 (13)	0.0263 (15)	0.0137 (15)
C7	0.071 (2)	0.097 (2)	0.107 (2)	0.0275 (16)	0.055 (2)	0.0299 (18)
C8	0.099 (2)	0.0854 (19)	0.0729 (18)	0.0385 (16)	0.0557 (18)	0.0165 (15)
C9	0.0744 (17)	0.0699 (16)	0.0524 (14)	0.0201 (12)	0.0314 (13)	0.0060 (11)
C10	0.0462 (13)	0.0466 (12)	0.0469 (12)	0.0053 (9)	0.0202 (10)	0.0050 (10)
C11	0.0666 (16)	0.0605 (15)	0.0488 (13)	0.0130 (11)	0.0183 (12)	0.0042 (11)
C12	0.0760 (18)	0.0735 (18)	0.0534 (14)	0.0112 (13)	0.0178 (13)	0.0155 (13)
C13	0.0641 (16)	0.0589 (16)	0.0776 (18)	0.0140 (12)	0.0231 (14)	0.0288 (14)
C14	0.0826 (19)	0.0440 (14)	0.0821 (19)	0.0086 (12)	0.0338 (15)	0.0080 (13)
C15	0.0689 (16)	0.0491 (14)	0.0594 (14)	0.0011 (11)	0.0252 (13)	0.0023 (11)
C16	0.0441 (13)	0.0448 (12)	0.0419 (11)	0.0042 (9)	0.0182 (10)	0.0043 (9)
C17	0.0479 (13)	0.0646 (14)	0.0443 (12)	−0.0005 (10)	0.0179 (10)	−0.0020 (10)
C18	0.0717 (18)	0.0718 (16)	0.0505 (13)	−0.0015 (12)	0.0333 (13)	−0.0079 (11)
C19	0.0574 (16)	0.0686 (16)	0.0766 (17)	0.0044 (12)	0.0443 (14)	−0.0072 (13)
C20	0.0426 (14)	0.0687 (16)	0.0772 (17)	0.0086 (11)	0.0229 (13)	0.0037 (13)
C21	0.0499 (14)	0.0579 (14)	0.0483 (12)	0.0049 (10)	0.0137 (11)	0.0024 (10)
C22	0.0556 (14)	0.0509 (13)	0.0428 (12)	0.0054 (11)	0.0265 (11)	0.0034 (10)
C23	0.0693 (16)	0.0610 (16)	0.0578 (14)	0.0009 (12)	0.0159 (12)	−0.0009 (12)
C24	0.099 (2)	0.0525 (16)	0.090 (2)	−0.0013 (14)	0.0403 (18)	−0.0033 (14)
C25	0.100 (2)	0.0663 (18)	0.0774 (19)	0.0235 (16)	0.0448 (18)	0.0224 (15)
C26	0.0833 (19)	0.0796 (19)	0.0526 (14)	0.0231 (15)	0.0185 (13)	0.0147 (14)
C27	0.0739 (17)	0.0601 (15)	0.0481 (13)	0.0113 (12)	0.0155 (12)	0.0034 (11)

Geometric parameters (Å, º)

Mg—N1^i	2.0266 (17)	C11—H11A	0.9300
Mg—N1	2.0266 (17)	C12—C13	1.364 (3)
Mg—N2	2.0439 (15)	C12—H12A	0.9300
Mg—N2^i	2.0439 (15)	C13—C14	1.356 (3)
F1—C13	1.359 (2)	C14—C15	1.374 (3)
F2—C19	1.358 (2)	C14—H14A	0.9300
N1—C1	1.341 (2)	C15—H15A	0.9300
N1—C4	1.426 (2)	C16—C17	1.390 (3)
N2—C3	1.333 (2)	C16—C21	1.391 (3)
N2—C22	1.424 (2)	C17—C18	1.385 (3)
C1—C2	1.402 (3)	C17—H17A	0.9300
C1—C10	1.492 (3)	C18—C19	1.356 (3)
C2—C3	1.404 (3)	C18—H18A	0.9300
C2—H2A	0.9300	C19—C20	1.362 (3)
C3—C16	1.498 (2)	C20—C21	1.385 (3)
C4—C5	1.379 (3)	C20—H20A	0.9300
C4—C9	1.389 (3)	C21—H21A	0.9300
C5—C6	1.378 (3)	C22—C23	1.381 (3)
C5—H5A	0.9300	C22—C27	1.386 (3)
C6—C7	1.370 (3)	C23—C24	1.386 (3)
C6—H6A	0.9300	C23—H23A	0.9300
C7—C8	1.369 (4)	C24—C25	1.366 (4)
C7—H7A	0.9300	C24—H24A	0.9300
C8—C9	1.389 (3)	C25—C26	1.373 (3)
C8—H8A	0.9300	C25—H25A	0.9300
C9—H9A	0.9300	C26—C27	1.388 (3)
C10—C11	1.384 (3)	C26—H26A	0.9300
C10—C15	1.386 (3)	C27—H27A	0.9300
C11—C12	1.376 (3)
N1—Mg—N1^i	118.76 (10)	C11—C12—H12A	120.9
N1^i—Mg—N2	114.47 (6)	C14—C13—F1	118.8 (2)
N1—Mg—N2	92.91 (6)	C14—C13—C12	123.0 (2)
N1^i—Mg—N2^i	92.91 (6)	F1—C13—C12	118.2 (2)
N1—Mg—N2^i	114.47 (6)	C13—C14—C15	118.1 (2)
N2—Mg—N2^i	125.67 (10)	C13—C14—H14A	121.0
C1—N1—C4	120.68 (16)	C15—C14—H14A	121.0
C1—N1—Mg	121.08 (13)	C14—C15—C10	121.5 (2)
C4—N1—Mg	117.98 (11)	C14—C15—H15A	119.3
C3—N2—C22	122.16 (15)	C10—C15—H15A	119.3
C3—N2—Mg	120.53 (13)	C17—C16—C21	118.28 (17)
C22—N2—Mg	117.28 (11)	C17—C16—C3	120.28 (18)
N1—C1—C2	123.07 (18)	C21—C16—C3	120.98 (17)
N1—C1—C10	120.29 (17)	C18—C17—C16	121.3 (2)
C2—C1—C10	116.61 (16)	C18—C17—H17A	119.4
C1—C2—C3	129.96 (17)	C16—C17—H17A	119.4
C1—C2—H2A	115.0	C19—C18—C17	118.1 (2)
C3—C2—H2A	115.0	C19—C18—H18A	120.9
N2—C3—C2	123.61 (16)	C17—C18—H18A	120.9
N2—C3—C16	122.05 (17)	F2—C19—C18	118.2 (2)
C2—C3—C16	114.24 (16)	F2—C19—C20	118.8 (2)
C5—C4—C9	118.4 (2)	C18—C19—C20	123.1 (2)
C5—C4—N1	121.67 (18)	C19—C20—C21	118.7 (2)
C9—C4—N1	119.3 (2)	C19—C20—H20A	120.7
C6—C5—C4	121.1 (2)	C21—C20—H20A	120.7
C6—C5—H5A	119.4	C20—C21—C16	120.5 (2)
C4—C5—H5A	119.4	C20—C21—H21A	119.7
C7—C6—C5	120.2 (3)	C16—C21—H21A	119.7
C7—C6—H6A	119.9	C23—C22—C27	118.5 (2)
C5—C6—H6A	119.9	C23—C22—N2	121.3 (2)
C6—C7—C8	119.8 (2)	C27—C22—N2	119.81 (19)
C6—C7—H7A	120.1	C22—C23—C24	120.8 (2)
C8—C7—H7A	120.1	C22—C23—H23A	119.6
C7—C8—C9	120.3 (2)	C24—C23—H23A	119.6
C7—C8—H8A	119.8	C25—C24—C23	120.3 (2)
C9—C8—H8A	119.8	C25—C24—H24A	119.9
C8—C9—C4	120.2 (2)	C23—C24—H24A	119.9
C8—C9—H9A	119.9	C24—C25—C26	119.8 (2)
C4—C9—H9A	119.9	C24—C25—H25A	120.1
C11—C10—C15	118.08 (19)	C26—C25—H25A	120.1
C11—C10—C1	121.73 (18)	C25—C26—C27	120.2 (2)
C15—C10—C1	120.18 (18)	C25—C26—H26A	119.9
C12—C11—C10	121.0 (2)	C27—C26—H26A	119.9
C12—C11—H11A	119.5	C26—C27—C22	120.5 (2)
C10—C11—H11A	119.5	C26—C27—H27A	119.8
C13—C12—C11	118.2 (2)	C22—C27—H27A	119.8
C13—C12—H12A	120.9

Symmetry code: (i) −x+1, y, −z+1/2.