Octahedral arrangement of trans-bis­(di­phenyl­propane­dionato)­bis(o-phenyl­enedi­amino)­zinc(II)

The title compound, [Zn(C₁₅H₁₁O₂)₂(C₆H₈N₂)₂], consists of a square-planar Zn^IIO₄ array, with two mol­ecules of axially coordinated 1,2-phenyl­enedi­amine. The Zn atom is located on a centre of symmetry. The monodentate trans arrangement of the di­amine mol­ecules results in the overall octahedral geometry. The phenyl groups adopt a butterfly-like conform­ation in relation to the ketoenolate frame. There are intramolecular N—H...O and intermolecular N—H...N hydrogen bonds; the N...O and N...N distances are 3.130 (4) and 3.323 (5) Å, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.086
• Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1B)             ?

PLAT_420  Alert C D-H Without Acceptor       N(2)   -   H(2B)             ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

bis-(1,2-diaminobenzene-N)-bis-(1,3-diphenyl-1,3-propanedionato-O,O)zinc(II)

Crystal data

[Zn(C15H11O2)2(C6H8N2)2]	F(000) = 760
Mr = 728.13	Dx = 1.379 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yn	Cell parameters from 49 reflections
a = 7.553 (1) Å	θ = 2.0–12.1°
b = 12.328 (2) Å	µ = 0.75 mm^−1
c = 19.038 (2) Å	T = 293 K
β = 98.317 (8)°	Prism, yellow
V = 1754.0 (4) Å^3	0.40 × 0.16 × 0.10 mm
Z = 2

Data collection

Siemens P4/PC diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = 0→8
ω scans	k = 0→14
3334 measured reflections	l = −22→22
3085 independent reflections	3 standard reflections every 97 reflections
1902 reflections with I > 2σ(I)	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
3085 reflections	Δρmax = 0.26 e Å^−3
245 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0108 (6)

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
Zn	0.5000	0.5000	1.0000	0.04089 (18)
O1	0.3924 (3)	0.59470 (18)	1.07258 (12)	0.0422 (6)
O2	0.4356 (3)	0.61529 (17)	0.92366 (12)	0.0418 (6)
N1	0.7709 (4)	0.5749 (3)	1.04287 (17)	0.0467 (8)
H1A	0.845 (5)	0.526 (3)	1.0323 (19)	0.056*
H1B	0.762 (5)	0.581 (3)	1.083 (2)	0.056*
N2	0.8834 (5)	0.5897 (3)	0.91102 (18)	0.0541 (9)
H2A	0.788 (5)	0.541 (3)	0.910 (2)	0.065*
H2B	0.894 (5)	0.602 (3)	0.870 (2)	0.065*
C1	0.3397 (4)	0.6921 (3)	1.06226 (17)	0.0356 (7)
C2	0.3294 (4)	0.7484 (3)	0.99785 (16)	0.0387 (8)
H2	0.2915	0.8201	0.9978	0.046*
C3	0.3702 (4)	0.7078 (3)	0.93392 (17)	0.0353 (7)
C4	0.3186 (4)	0.7766 (3)	0.86886 (16)	0.0356 (7)
C5	0.3434 (5)	0.8876 (3)	0.86921 (19)	0.0504 (9)
H5	0.4030	0.9211	0.9096	0.060*
C6	0.2805 (6)	0.9498 (3)	0.8100 (2)	0.0699 (13)
H6	0.3001	1.0243	0.8106	0.084*
C7	0.1891 (6)	0.9009 (4)	0.7505 (2)	0.0693 (13)
H7	0.1430	0.9428	0.7115	0.083*
C8	0.1661 (5)	0.7910 (4)	0.74881 (19)	0.0596 (11)
H8	0.1068	0.7579	0.7082	0.072*
C9	0.2310 (5)	0.7289 (3)	0.80751 (17)	0.0468 (9)
H9	0.2156	0.6540	0.8058	0.056*
C10	0.2734 (4)	0.7475 (3)	1.12405 (16)	0.0361 (8)
C11	0.2822 (5)	0.8587 (3)	1.13312 (19)	0.0496 (9)
H11	0.3313	0.9015	1.1006	0.059*
C12	0.2182 (6)	0.9073 (3)	1.1907 (2)	0.0633 (11)
H12	0.2249	0.9822	1.1965	0.076*
C13	0.1448 (5)	0.8442 (4)	1.2390 (2)	0.0602 (11)
H13	0.1002	0.8766	1.2769	0.072*
C14	0.1379 (5)	0.7336 (4)	1.2310 (2)	0.0567 (11)
H14	0.0896	0.6909	1.2638	0.068*
C15	0.2026 (5)	0.6858 (3)	1.17439 (18)	0.0471 (9)
H15	0.1988	0.6107	1.1698	0.056*
C16	0.8107 (4)	0.6797 (3)	1.01656 (18)	0.0397 (8)
C17	0.8579 (4)	0.6870 (3)	0.94775 (18)	0.0407 (8)
C18	0.8841 (5)	0.7880 (3)	0.9207 (2)	0.0506 (9)
H18	0.9123	0.7939	0.8749	0.061*
C19	0.8696 (5)	0.8807 (3)	0.9596 (2)	0.0593 (11)
H19	0.8897	0.9483	0.9405	0.071*
C20	0.8252 (5)	0.8730 (3)	1.0267 (2)	0.0598 (11)
H20	0.8139	0.9354	1.0530	0.072*
C21	0.7972 (5)	0.7724 (3)	1.0551 (2)	0.0502 (9)
H21	0.7689	0.7675	1.1010	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0505 (3)	0.0317 (3)	0.0443 (3)	0.0079 (3)	0.0197 (2)	0.0061 (3)
O1	0.0552 (15)	0.0356 (13)	0.0389 (13)	0.0107 (11)	0.0176 (11)	0.0046 (11)
O2	0.0546 (15)	0.0316 (13)	0.0427 (14)	0.0069 (11)	0.0192 (11)	0.0053 (10)
N1	0.053 (2)	0.0456 (19)	0.0441 (18)	0.0066 (15)	0.0160 (16)	0.0071 (16)
N2	0.062 (2)	0.052 (2)	0.053 (2)	−0.0030 (17)	0.0245 (18)	−0.0079 (17)
C1	0.0369 (18)	0.0358 (18)	0.0350 (18)	0.0044 (15)	0.0085 (14)	−0.0013 (15)
C2	0.048 (2)	0.0316 (17)	0.0368 (18)	0.0093 (16)	0.0088 (15)	0.0012 (15)
C3	0.0356 (18)	0.0321 (18)	0.0390 (18)	0.0020 (15)	0.0086 (14)	0.0007 (15)
C4	0.0387 (18)	0.0371 (19)	0.0323 (17)	0.0062 (15)	0.0100 (14)	−0.0004 (15)
C5	0.069 (3)	0.042 (2)	0.040 (2)	0.0090 (19)	0.0073 (19)	−0.0001 (17)
C6	0.107 (4)	0.044 (2)	0.061 (3)	0.022 (2)	0.020 (3)	0.016 (2)
C7	0.082 (3)	0.088 (4)	0.038 (2)	0.035 (3)	0.010 (2)	0.020 (2)
C8	0.054 (2)	0.095 (3)	0.028 (2)	0.012 (2)	0.0005 (17)	−0.006 (2)
C9	0.046 (2)	0.055 (2)	0.041 (2)	0.0010 (18)	0.0121 (17)	−0.0057 (18)
C10	0.0327 (18)	0.0397 (19)	0.0350 (18)	0.0058 (15)	0.0022 (14)	−0.0039 (15)
C11	0.067 (3)	0.040 (2)	0.042 (2)	0.0071 (18)	0.0089 (19)	−0.0027 (17)
C12	0.086 (3)	0.048 (2)	0.054 (3)	0.014 (2)	0.008 (2)	−0.013 (2)
C13	0.067 (3)	0.078 (3)	0.037 (2)	0.015 (2)	0.0093 (19)	−0.018 (2)
C14	0.056 (2)	0.071 (3)	0.046 (2)	0.005 (2)	0.0188 (19)	−0.002 (2)
C15	0.047 (2)	0.050 (2)	0.046 (2)	0.0025 (17)	0.0129 (17)	−0.0032 (18)
C16	0.0322 (18)	0.0369 (19)	0.050 (2)	0.0028 (15)	0.0061 (15)	0.0007 (16)
C17	0.0357 (19)	0.041 (2)	0.046 (2)	−0.0020 (16)	0.0086 (16)	−0.0008 (16)
C18	0.044 (2)	0.054 (2)	0.053 (2)	−0.0022 (18)	0.0059 (18)	0.0095 (19)
C19	0.051 (2)	0.044 (2)	0.081 (3)	−0.0048 (19)	0.003 (2)	0.012 (2)
C20	0.056 (2)	0.042 (2)	0.081 (3)	0.0015 (19)	0.008 (2)	−0.013 (2)
C21	0.046 (2)	0.057 (2)	0.048 (2)	−0.0003 (19)	0.0095 (17)	−0.0098 (19)

Geometric parameters (Å, º)

Zn—O2^i	2.041 (2)	C7—H7	0.9300
Zn—O2	2.041 (2)	C8—C9	1.385 (5)
Zn—O1^i	2.063 (2)	C8—H8	0.9300
Zn—O1	2.063 (2)	C9—H9	0.9300
Zn—N1^i	2.285 (4)	C10—C11	1.383 (5)
Zn—N1	2.285 (4)	C10—C15	1.390 (5)
O1—C1	1.271 (4)	C11—C12	1.395 (5)
O2—C3	1.270 (4)	C11—H11	0.9300
N1—C16	1.434 (5)	C12—C13	1.381 (6)
N1—H1A	0.86 (4)	C12—H12	0.9300
N1—H1B	0.78 (4)	C13—C14	1.372 (6)
N2—C17	1.415 (5)	C13—H13	0.9300
N2—H2A	0.94 (4)	C14—C15	1.378 (5)
N2—H2B	0.81 (4)	C14—H14	0.9300
C1—C2	1.401 (4)	C15—H15	0.9300
C1—C10	1.507 (4)	C16—C21	1.370 (5)
C2—C3	1.391 (4)	C16—C17	1.409 (5)
C2—H2	0.9300	C17—C18	1.373 (5)
C3—C4	1.505 (4)	C18—C19	1.376 (5)
C4—C5	1.380 (5)	C18—H18	0.9300
C4—C9	1.388 (5)	C19—C20	1.368 (6)
C5—C6	1.389 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.382 (5)
C6—C7	1.377 (6)	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.366 (6)
O2^i—Zn—O2	180.000 (1)	C8—C7—H7	120.0
O2^i—Zn—O1^i	90.38 (9)	C6—C7—H7	120.0
O2—Zn—O1^i	89.62 (9)	C7—C8—C9	120.0 (4)
O2^i—Zn—O1	89.62 (9)	C7—C8—H8	120.0
O2—Zn—O1	90.38 (9)	C9—C8—H8	120.0
O1^i—Zn—O1	180.00 (8)	C8—C9—C4	121.0 (4)
O2^i—Zn—N1^i	94.70 (10)	C8—C9—H9	119.5
O2—Zn—N1^i	85.30 (10)	C4—C9—H9	119.5
O1^i—Zn—N1^i	87.21 (11)	C11—C10—C15	118.2 (3)
O1—Zn—N1^i	92.79 (11)	C11—C10—C1	122.1 (3)
O2^i—Zn—N1	85.30 (10)	C15—C10—C1	119.6 (3)
O2—Zn—N1	94.70 (10)	C10—C11—C12	120.5 (4)
O1^i—Zn—N1	92.79 (11)	C10—C11—H11	119.7
O1—Zn—N1	87.21 (11)	C12—C11—H11	119.7
N1^i—Zn—N1	180.0	C13—C12—C11	120.0 (4)
C1—O1—Zn	125.2 (2)	C13—C12—H12	120.0
C3—O2—Zn	125.0 (2)	C11—C12—H12	120.0
C16—N1—Zn	117.5 (2)	C14—C13—C12	119.9 (4)
C16—N1—H1A	112 (2)	C14—C13—H13	120.0
Zn—N1—H1A	102 (3)	C12—C13—H13	120.0
C16—N1—H1B	108 (3)	C13—C14—C15	120.0 (4)
Zn—N1—H1B	101 (3)	C13—C14—H14	120.0
H1A—N1—H1B	116 (4)	C15—C14—H14	120.0
C17—N2—H2A	114 (2)	C14—C15—C10	121.4 (4)
C17—N2—H2B	111 (3)	C14—C15—H15	119.3
H2A—N2—H2B	107 (4)	C10—C15—H15	119.3
O1—C1—C2	125.4 (3)	C21—C16—C17	119.6 (3)
O1—C1—C10	116.1 (3)	C21—C16—N1	121.9 (3)
C2—C1—C10	118.4 (3)	C17—C16—N1	118.4 (3)
C3—C2—C1	126.6 (3)	C18—C17—C16	118.4 (3)
C3—C2—H2	116.7	C18—C17—N2	123.1 (3)
C1—C2—H2	116.7	C16—C17—N2	118.4 (3)
O2—C3—C2	126.7 (3)	C17—C18—C19	121.7 (4)
O2—C3—C4	116.1 (3)	C17—C18—H18	119.2
C2—C3—C4	117.0 (3)	C19—C18—H18	119.2
C5—C4—C9	118.2 (3)	C20—C19—C18	119.6 (4)
C5—C4—C3	122.4 (3)	C20—C19—H19	120.2
C9—C4—C3	119.3 (3)	C18—C19—H19	120.2
C4—C5—C6	120.9 (4)	C19—C20—C21	120.0 (4)
C4—C5—H5	119.6	C19—C20—H20	120.0
C6—C5—H5	119.6	C21—C20—H20	120.0
C7—C6—C5	119.8 (4)	C16—C21—C20	120.7 (3)
C7—C6—H6	120.1	C16—C21—H21	119.7
C5—C6—H6	120.1	C20—C21—H21	119.7
C8—C7—C6	120.1 (4)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2^ii	0.86 (4)	2.61 (4)	3.323 (5)	142 (3)
N1—H1B···O1	0.78 (4)	2.77 (4)	3.003 (4)	99 (3)
N2—H2A···O1^i	0.94 (4)	2.21 (4)	3.130 (4)	166 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2.