Dichloro­(N,N′-dibenzyl­ethane-1,2-diamine-κ²N,N)zinc(II)

In the title compound, [ZnCl₂(C₁₆H₂₀N₂)], the Zn cation is coordinated by two Cl anions and two N atoms of N,N′-dibenzyl­ethane-1,2-diamine in a distorted tetra­hedral geometry. The mol­ecules are linked into dimers by N—H...Cl and C—H...Cl hydrogen bonds; neighboring dimers are linked into a sheet by C—H... Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.029
• wR factor = 0.071
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  CL1     ..       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  CL2     ..       2.90 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dichloro(N,N'-dibenzylethane-1,2-diamine-κ²N,N)zinc(II)

Crystal data

[ZnCl2(C8H10N)2]	F(000) = 776
Mr = 376.61	Dx = 1.417 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3123 reflections
a = 10.760 (3) Å	θ = 2.5–26.4°
b = 16.179 (4) Å	µ = 1.69 mm^−1
c = 10.261 (3) Å	T = 293 K
β = 98.783 (3)°	Block, colourless
V = 1765.4 (8) Å^3	0.36 × 0.28 × 0.15 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	3096 independent reflections
Radiation source: fine-focus sealed tube	2232 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.582, Tmax = 0.786	k = −18→19
9067 measured reflections	l = −12→9

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0279P)^2 + 0.5191P] where P = (Fo^2 + 2Fc^2)/3
3096 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.18 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
Zn	0.75254 (3)	0.497103 (19)	0.58378 (3)	0.04483 (11)
Cl1	0.93671 (6)	0.51525 (5)	0.71344 (7)	0.0599 (2)
Cl2	0.59879 (7)	0.42554 (5)	0.64814 (8)	0.0598 (2)
N1	0.6943 (2)	0.61104 (13)	0.5075 (2)	0.0466 (5)
H1	0.6093	0.6092	0.4843	0.056*
N2	0.7863 (2)	0.46578 (14)	0.3969 (2)	0.0459 (5)
H2A	0.8710	0.4668	0.3981	0.055*
C1	0.6818 (3)	0.76488 (17)	0.5421 (3)	0.0530 (7)
C2	0.5564 (4)	0.7855 (2)	0.5225 (4)	0.0822 (11)
H2	0.4978	0.7477	0.5441	0.099*
C3	0.5164 (4)	0.8607 (3)	0.4718 (4)	0.1051 (15)
H3	0.4314	0.8738	0.4610	0.126*
C4	0.5995 (6)	0.9160 (3)	0.4374 (4)	0.0998 (15)
H4	0.5716	0.9667	0.4015	0.120*
C5	0.7226 (5)	0.8977 (2)	0.4551 (4)	0.0934 (13)
H5	0.7798	0.9358	0.4312	0.112*
C6	0.7650 (3)	0.8219 (2)	0.5092 (3)	0.0729 (10)
H6	0.8506	0.8101	0.5229	0.087*
C7	0.7246 (3)	0.68199 (17)	0.5986 (3)	0.0627 (8)
H7A	0.8149	0.6838	0.6258	0.075*
H7B	0.6863	0.6724	0.6769	0.075*
C8	0.7504 (3)	0.61631 (18)	0.3850 (3)	0.0583 (8)
H8A	0.8395	0.6285	0.4063	0.070*
H8B	0.7108	0.6605	0.3298	0.070*
C9	0.7318 (3)	0.53483 (18)	0.3118 (3)	0.0564 (8)
H9A	0.6427	0.5252	0.2844	0.068*
H9B	0.7718	0.5373	0.2334	0.068*
C10	0.7401 (3)	0.38520 (17)	0.3424 (3)	0.0582 (8)
H10A	0.7543	0.3822	0.2514	0.070*
H10B	0.6500	0.3827	0.3422	0.070*
C11	0.7993 (3)	0.31074 (18)	0.4144 (3)	0.0499 (7)
C12	0.8832 (3)	0.3142 (2)	0.5289 (3)	0.0628 (8)
H12	0.9081	0.3653	0.5655	0.075*
C13	0.9315 (3)	0.2425 (2)	0.5911 (3)	0.0724 (10)
H13	0.9867	0.2457	0.6700	0.087*
C14	0.8983 (3)	0.1669 (2)	0.5369 (4)	0.0740 (10)
H14	0.9315	0.1188	0.5777	0.089*
C15	0.8157 (4)	0.1632 (2)	0.4220 (4)	0.0829 (11)
H15	0.7926	0.1121	0.3845	0.099*
C16	0.7665 (3)	0.2339 (2)	0.3611 (3)	0.0719 (9)
H16	0.7103	0.2302	0.2829	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.04210 (18)	0.04702 (19)	0.04517 (19)	−0.00231 (15)	0.00606 (13)	0.00190 (15)
Cl1	0.0424 (4)	0.0798 (6)	0.0561 (4)	−0.0076 (4)	0.0025 (3)	−0.0091 (4)
Cl2	0.0432 (4)	0.0678 (5)	0.0687 (5)	−0.0074 (3)	0.0097 (3)	0.0119 (4)
N1	0.0420 (13)	0.0481 (13)	0.0498 (14)	−0.0003 (10)	0.0077 (10)	0.0024 (11)
N2	0.0381 (12)	0.0549 (14)	0.0451 (13)	0.0010 (11)	0.0075 (10)	−0.0004 (11)
C1	0.062 (2)	0.0465 (17)	0.0513 (18)	0.0024 (15)	0.0101 (15)	−0.0038 (13)
C2	0.069 (2)	0.064 (2)	0.111 (3)	0.0006 (19)	0.007 (2)	0.005 (2)
C3	0.094 (3)	0.085 (3)	0.129 (4)	0.030 (3)	−0.007 (3)	0.004 (3)
C4	0.172 (5)	0.065 (3)	0.062 (2)	0.037 (3)	0.019 (3)	0.0025 (19)
C5	0.159 (4)	0.051 (2)	0.086 (3)	−0.012 (3)	0.070 (3)	−0.0019 (19)
C6	0.079 (2)	0.059 (2)	0.089 (3)	−0.0043 (18)	0.039 (2)	−0.0103 (19)
C7	0.075 (2)	0.0499 (18)	0.060 (2)	−0.0002 (16)	0.0004 (16)	−0.0021 (15)
C8	0.0585 (19)	0.0555 (19)	0.063 (2)	0.0030 (15)	0.0164 (16)	0.0147 (15)
C9	0.0582 (18)	0.0677 (19)	0.0445 (17)	0.0099 (16)	0.0115 (14)	0.0099 (15)
C10	0.0571 (18)	0.0629 (19)	0.0530 (19)	−0.0010 (16)	0.0037 (14)	−0.0131 (15)
C11	0.0480 (16)	0.0549 (18)	0.0488 (18)	0.0025 (14)	0.0137 (13)	−0.0070 (14)
C12	0.0571 (19)	0.059 (2)	0.070 (2)	0.0091 (16)	0.0037 (16)	−0.0110 (16)
C13	0.060 (2)	0.087 (3)	0.068 (2)	0.0191 (19)	0.0028 (17)	0.0010 (19)
C14	0.076 (2)	0.065 (2)	0.086 (3)	0.0110 (19)	0.027 (2)	0.013 (2)
C15	0.099 (3)	0.056 (2)	0.095 (3)	−0.004 (2)	0.017 (2)	−0.007 (2)
C16	0.086 (3)	0.064 (2)	0.064 (2)	−0.0047 (19)	0.0068 (18)	−0.0113 (18)

Geometric parameters (Å, º)

Zn—N1	2.063 (2)	C7—H7A	0.9700
Zn—N2	2.069 (2)	C7—H7B	0.9700
Zn—Cl2	2.2017 (9)	C8—C9	1.515 (4)
Zn—Cl1	2.2311 (8)	C8—H8A	0.9700
N1—C8	1.477 (3)	C8—H8B	0.9700
N1—C7	1.485 (3)	C9—H9A	0.9700
N1—H1	0.9100	C9—H9B	0.9700
N2—C10	1.474 (3)	C10—C11	1.503 (4)
N2—C9	1.482 (3)	C10—H10A	0.9700
N2—H2A	0.9100	C10—H10B	0.9700
C1—C6	1.364 (4)	C11—C12	1.370 (4)
C1—C2	1.374 (4)	C11—C16	1.381 (4)
C1—C7	1.505 (4)	C12—C13	1.387 (4)
C2—C3	1.366 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.367 (4)
C3—C4	1.350 (6)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.365 (5)
C4—C5	1.341 (6)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.370 (4)
C5—C6	1.394 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300
N1—Zn—N2	87.31 (9)	N1—C7—H7B	108.5
N1—Zn—Cl2	112.65 (7)	C1—C7—H7B	108.5
N2—Zn—Cl2	113.29 (7)	H7A—C7—H7B	107.5
N1—Zn—Cl1	107.43 (6)	N1—C8—C9	109.3 (2)
N2—Zn—Cl1	108.63 (7)	N1—C8—H8A	109.8
Cl2—Zn—Cl1	122.01 (3)	C9—C8—H8A	109.8
C8—N1—C7	114.3 (2)	N1—C8—H8B	109.8
C8—N1—Zn	103.56 (16)	C9—C8—H8B	109.8
C7—N1—Zn	115.27 (16)	H8A—C8—H8B	108.3
C8—N1—H1	107.8	N2—C9—C8	110.7 (2)
C7—N1—H1	107.8	N2—C9—H9A	109.5
Zn—N1—H1	107.8	C8—C9—H9A	109.5
C10—N2—C9	111.3 (2)	N2—C9—H9B	109.5
C10—N2—Zn	118.16 (18)	C8—C9—H9B	109.5
C9—N2—Zn	104.58 (16)	H9A—C9—H9B	108.1
C10—N2—H2A	107.4	N2—C10—C11	115.4 (2)
C9—N2—H2A	107.4	N2—C10—H10A	108.4
Zn—N2—H2A	107.4	C11—C10—H10A	108.4
C6—C1—C2	117.8 (3)	N2—C10—H10B	108.4
C6—C1—C7	121.6 (3)	C11—C10—H10B	108.4
C2—C1—C7	120.6 (3)	H10A—C10—H10B	107.5
C3—C2—C1	121.1 (4)	C12—C11—C16	118.1 (3)
C3—C2—H2	119.4	C12—C11—C10	124.3 (3)
C1—C2—H2	119.4	C16—C11—C10	117.6 (3)
C4—C3—C2	120.5 (4)	C11—C12—C13	120.8 (3)
C4—C3—H3	119.8	C11—C12—H12	119.6
C2—C3—H3	119.8	C13—C12—H12	119.6
C5—C4—C3	119.9 (4)	C14—C13—C12	120.3 (3)
C5—C4—H4	120.1	C14—C13—H13	119.8
C3—C4—H4	120.1	C12—C13—H13	119.8
C4—C5—C6	120.3 (4)	C15—C14—C13	119.1 (3)
C4—C5—H5	119.9	C15—C14—H14	120.5
C6—C5—H5	119.9	C13—C14—H14	120.5
C1—C6—C5	120.4 (4)	C14—C15—C16	120.8 (3)
C1—C6—H6	119.8	C14—C15—H15	119.6
C5—C6—H6	119.8	C16—C15—H15	119.6
N1—C7—C1	114.9 (2)	C15—C16—C11	120.9 (3)
N1—C7—H7A	108.5	C15—C16—H16	119.6
C1—C7—H7A	108.5	C11—C16—H16	119.6
N2—Zn—N1—C8	−19.43 (17)	Zn—N1—C7—C1	180.0 (2)
Cl2—Zn—N1—C8	−133.59 (15)	C6—C1—C7—N1	−107.8 (3)
Cl1—Zn—N1—C8	89.27 (16)	C2—C1—C7—N1	72.5 (4)
N2—Zn—N1—C7	−145.1 (2)	C7—N1—C8—C9	170.5 (2)
Cl2—Zn—N1—C7	100.76 (19)	Zn—N1—C8—C9	44.2 (2)
Cl1—Zn—N1—C7	−36.4 (2)	C10—N2—C9—C8	164.6 (2)
N1—Zn—N2—C10	−133.22 (19)	Zn—N2—C9—C8	35.9 (3)
Cl2—Zn—N2—C10	−19.7 (2)	N1—C8—C9—N2	−56.7 (3)
Cl1—Zn—N2—C10	119.28 (17)	C9—N2—C10—C11	174.3 (2)
N1—Zn—N2—C9	−8.84 (17)	Zn—N2—C10—C11	−64.7 (3)
Cl2—Zn—N2—C9	104.71 (16)	N2—C10—C11—C12	5.1 (4)
Cl1—Zn—N2—C9	−116.34 (16)	N2—C10—C11—C16	−175.0 (3)
C6—C1—C2—C3	0.0 (5)	C16—C11—C12—C13	−1.4 (5)
C7—C1—C2—C3	179.7 (3)	C10—C11—C12—C13	178.5 (3)
C1—C2—C3—C4	1.2 (6)	C11—C12—C13—C14	1.7 (5)
C2—C3—C4—C5	−1.1 (7)	C12—C13—C14—C15	−0.9 (5)
C3—C4—C5—C6	−0.1 (6)	C13—C14—C15—C16	0.1 (6)
C2—C1—C6—C5	−1.3 (5)	C14—C15—C16—C11	0.1 (6)
C7—C1—C6—C5	179.0 (3)	C12—C11—C16—C15	0.6 (5)
C4—C5—C6—C1	1.4 (6)	C10—C11—C16—C15	−179.3 (3)
C8—N1—C7—C1	60.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.91	2.53	3.361 (2)	152
C14—H14···Cl1^ii	0.93	2.91	3.788 (4)	158
C9—H9A···Cl2^iii	0.97	2.90	3.699 (3)	140
N1—H1···Cl2^iii	0.91	2.50	3.363 (2)	159

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1.