Bis{2-[1-(benzyl­imino)eth­yl]-5-methoxy­phenol}dichloro­zinc(II)

The title complex, [ZnCl₂(C₁₆H₁₇NO₂)₂], displays a distorted tetra­hedral coordination geometry around the Zn^II ion. The Schiff base inner salt, (benzyl­imino)ethyl-5-methoxy­phenol, coordinates in a monodentate manner to the Zn^II ion via the deprotonated hydr­oxy groups. The protonated imino groups form intra­molecular hydrogen bonds with the deprotonated hydroxyl groups of the same Schiff base ligand.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.042
• wR factor = 0.119
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.80 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C11    -C16           1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C27    -C32           1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

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

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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'.

Bis{2-[1-(benzylimino)ethyl]-5-methoxyphenol}dichlorozinc(II)

Crystal data

[ZnCl2(C16H17NO2)2]	F(000) = 1344
Mr = 646.88	Dx = 1.375 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3722 reflections
a = 11.1785 (18) Å	θ = 2.2–24.7°
b = 16.082 (3) Å	µ = 1.00 mm^−1
c = 17.555 (3) Å	T = 298 K
β = 97.928 (3)°	Prism, colorless
V = 3125.7 (9) Å^3	0.49 × 0.45 × 0.40 mm
Z = 4

Data collection

Bruker APEX area-dectector diffractometer	5827 independent reflections
Radiation source: fine-focus sealed tube	3546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→9
Tmin = 0.618, Tmax = 0.670	k = −19→18
16847 measured reflections	l = −18→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0436P)^2 + 1.2861P] where P = (Fo^2 + 2Fc^2)/3
5827 reflections	(Δ/σ)max = 0.001
374 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.30 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.29374 (4)	0.09695 (2)	0.23116 (2)	0.04291 (15)
Cl1	0.47070 (9)	0.10392 (6)	0.18634 (6)	0.0641 (3)
Cl2	0.12456 (10)	0.11924 (6)	0.15182 (6)	0.0697 (3)
N1	0.4291 (3)	0.30481 (18)	0.36804 (18)	0.0508 (8)
H1	0.3970	0.2574	0.3378	0.076*
N2	0.1462 (3)	−0.14823 (19)	0.2369 (2)	0.0589 (9)
H2	0.1585	−0.0890	0.2300	0.088*
O1	0.3161 (2)	0.17401 (14)	0.31878 (13)	0.0501 (6)
O2	−0.0102 (3)	0.0823 (2)	0.44542 (18)	0.0821 (9)
O3	0.2675 (2)	−0.01628 (13)	0.27106 (14)	0.0507 (7)
O4	0.6306 (3)	−0.0392 (2)	0.44718 (18)	0.0862 (10)
C1	0.3787 (4)	0.3823 (2)	0.4771 (2)	0.0674 (12)
H1A	0.4350	0.4208	0.4600	0.101*
H1B	0.4101	0.3619	0.5273	0.101*
H1C	0.3031	0.4099	0.4793	0.101*
C2	0.3596 (3)	0.3109 (2)	0.4219 (2)	0.0466 (9)
C3	0.2677 (3)	0.2492 (2)	0.4269 (2)	0.0437 (9)
C4	0.2475 (3)	0.1829 (2)	0.3732 (2)	0.0441 (9)
C5	0.1533 (3)	0.1272 (2)	0.3791 (2)	0.0527 (10)
H5	0.1379	0.0847	0.3431	0.063*
C6	0.0835 (4)	0.1337 (3)	0.4365 (2)	0.0584 (11)
C7	0.1044 (4)	0.1975 (3)	0.4915 (2)	0.0615 (11)
H7	0.0574	0.2015	0.5312	0.074*
C8	0.1932 (4)	0.2526 (3)	0.4860 (2)	0.0552 (10)
H8	0.2063	0.2947	0.5224	0.066*
C9	−0.0315 (5)	0.0133 (3)	0.3932 (3)	0.1003 (18)
H9A	−0.0497	0.0337	0.3415	0.150*
H9B	−0.0984	−0.0189	0.4060	0.150*
H9C	0.0394	−0.0211	0.3974	0.150*
C10	0.5236 (4)	0.3619 (2)	0.3527 (2)	0.0612 (11)
H10A	0.4939	0.4184	0.3550	0.073*
H10B	0.5414	0.3523	0.3009	0.073*
C11	0.6385 (3)	0.3537 (2)	0.4079 (2)	0.0541 (10)
C12	0.7082 (4)	0.4230 (3)	0.4273 (3)	0.0667 (12)
H12	0.6829	0.4746	0.4072	0.080*
C13	0.8150 (4)	0.4163 (3)	0.4762 (3)	0.0816 (14)
H13	0.8616	0.4636	0.4883	0.098*
C14	0.8534 (4)	0.3423 (4)	0.5069 (3)	0.0909 (16)
H14	0.9254	0.3386	0.5403	0.109*
C15	0.7849 (5)	0.2733 (4)	0.4882 (4)	0.113 (2)
H15	0.8103	0.2221	0.5090	0.135*
C16	0.6782 (4)	0.2790 (3)	0.4387 (3)	0.0879 (16)
H16	0.6328	0.2313	0.4260	0.105*
C17	0.2157 (5)	−0.2843 (3)	0.2825 (3)	0.1030 (19)
H17A	0.1588	−0.2986	0.3166	0.155*
H17B	0.2928	−0.3085	0.3009	0.155*
H17C	0.1876	−0.3053	0.2320	0.155*
C18	0.2281 (4)	−0.1907 (2)	0.2792 (2)	0.0557 (10)
C19	0.3291 (3)	−0.1488 (2)	0.3218 (2)	0.0501 (10)
C20	0.3453 (3)	−0.0610 (2)	0.3166 (2)	0.0428 (9)
C21	0.4466 (3)	−0.0241 (2)	0.3592 (2)	0.0488 (9)
H21	0.4572	0.0331	0.3565	0.059*
C22	0.5298 (4)	−0.0706 (3)	0.4045 (2)	0.0601 (11)
C23	0.5165 (4)	−0.1559 (3)	0.4092 (3)	0.0762 (14)
H23	0.5747	−0.1874	0.4393	0.091*
C24	0.4189 (4)	−0.1931 (3)	0.3699 (3)	0.0715 (13)
H24	0.4103	−0.2503	0.3747	0.086*
C25	0.6517 (4)	0.0472 (3)	0.4445 (3)	0.0897 (16)
H25A	0.6615	0.0630	0.3930	0.135*
H25B	0.7236	0.0608	0.4787	0.135*
H25C	0.5842	0.0765	0.4601	0.135*
C26	0.0353 (4)	−0.1775 (3)	0.1897 (3)	0.0787 (14)
H26A	0.0240	−0.2362	0.1991	0.094*
H26B	0.0427	−0.1705	0.1357	0.094*
C27	−0.0723 (4)	−0.1297 (2)	0.2084 (2)	0.0524 (10)
C28	−0.1043 (5)	−0.0562 (3)	0.1728 (3)	0.0766 (14)
H28	−0.0586	−0.0351	0.1368	0.092*
C29	−0.2036 (7)	−0.0129 (4)	0.1895 (4)	0.108 (2)
H29	−0.2262	0.0366	0.1640	0.129*
C30	−0.2680 (6)	−0.0427 (5)	0.2434 (5)	0.120 (3)
H30	−0.3344	−0.0133	0.2555	0.144*
C31	−0.2362 (5)	−0.1154 (5)	0.2796 (3)	0.0990 (19)
H31	−0.2811	−0.1358	0.3163	0.119*
C32	−0.1388 (5)	−0.1587 (3)	0.2624 (3)	0.0704 (13)
H32	−0.1174	−0.2084	0.2877	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0530 (3)	0.0355 (2)	0.0389 (2)	0.0015 (2)	0.00188 (18)	−0.00023 (19)
Cl1	0.0606 (7)	0.0678 (7)	0.0661 (7)	−0.0070 (5)	0.0169 (5)	−0.0011 (5)
Cl2	0.0670 (7)	0.0671 (7)	0.0673 (7)	−0.0001 (5)	−0.0178 (6)	0.0145 (5)
N1	0.054 (2)	0.0464 (18)	0.048 (2)	−0.0033 (15)	−0.0038 (16)	−0.0040 (15)
N2	0.058 (2)	0.0448 (18)	0.074 (2)	−0.0037 (17)	0.0121 (18)	−0.0070 (17)
O1	0.0597 (17)	0.0463 (14)	0.0455 (15)	−0.0017 (12)	0.0113 (13)	−0.0136 (12)
O2	0.069 (2)	0.106 (2)	0.074 (2)	−0.0251 (19)	0.0192 (17)	0.0006 (19)
O3	0.0559 (16)	0.0354 (13)	0.0576 (17)	0.0030 (12)	−0.0036 (13)	0.0079 (12)
O4	0.070 (2)	0.098 (3)	0.083 (2)	0.0092 (19)	−0.0151 (18)	0.009 (2)
C1	0.077 (3)	0.060 (3)	0.062 (3)	0.001 (2)	−0.003 (2)	−0.019 (2)
C2	0.052 (2)	0.048 (2)	0.037 (2)	0.0136 (19)	−0.0047 (18)	−0.0005 (17)
C3	0.048 (2)	0.043 (2)	0.038 (2)	0.0102 (18)	−0.0007 (17)	−0.0014 (16)
C4	0.050 (2)	0.044 (2)	0.037 (2)	0.0113 (18)	0.0003 (17)	0.0011 (17)
C5	0.055 (3)	0.059 (2)	0.044 (2)	0.000 (2)	0.0042 (19)	−0.0055 (18)
C6	0.051 (3)	0.067 (3)	0.056 (3)	−0.003 (2)	0.001 (2)	0.003 (2)
C7	0.054 (3)	0.082 (3)	0.051 (3)	0.007 (2)	0.015 (2)	−0.004 (2)
C8	0.057 (3)	0.064 (3)	0.043 (2)	0.014 (2)	0.0021 (19)	−0.0120 (19)
C9	0.106 (4)	0.110 (4)	0.084 (4)	−0.049 (3)	0.010 (3)	−0.009 (3)
C10	0.070 (3)	0.059 (2)	0.053 (3)	−0.009 (2)	0.002 (2)	0.004 (2)
C11	0.055 (3)	0.052 (2)	0.056 (3)	−0.005 (2)	0.009 (2)	0.0026 (19)
C12	0.075 (3)	0.054 (3)	0.069 (3)	−0.002 (2)	0.002 (2)	−0.008 (2)
C13	0.072 (3)	0.084 (4)	0.086 (4)	−0.009 (3)	0.001 (3)	−0.020 (3)
C14	0.054 (3)	0.124 (5)	0.090 (4)	0.002 (3)	−0.005 (3)	0.007 (4)
C15	0.065 (4)	0.101 (4)	0.164 (6)	0.001 (3)	−0.015 (4)	0.047 (4)
C16	0.061 (3)	0.064 (3)	0.132 (5)	−0.009 (2)	−0.011 (3)	0.023 (3)
C17	0.109 (4)	0.039 (2)	0.159 (5)	−0.004 (3)	0.012 (4)	0.008 (3)
C18	0.062 (3)	0.037 (2)	0.073 (3)	0.0033 (19)	0.028 (2)	0.003 (2)
C19	0.053 (3)	0.041 (2)	0.059 (3)	0.0070 (19)	0.0181 (19)	0.0060 (18)
C20	0.046 (2)	0.0422 (19)	0.043 (2)	0.0095 (17)	0.0155 (17)	0.0056 (17)
C21	0.052 (2)	0.048 (2)	0.047 (2)	0.0061 (19)	0.0104 (19)	0.0079 (18)
C22	0.055 (3)	0.071 (3)	0.054 (3)	0.009 (2)	0.007 (2)	0.008 (2)
C23	0.064 (3)	0.074 (3)	0.087 (4)	0.024 (3)	0.000 (3)	0.029 (3)
C24	0.075 (3)	0.047 (2)	0.095 (4)	0.015 (2)	0.020 (3)	0.023 (2)
C25	0.070 (4)	0.112 (4)	0.084 (4)	−0.018 (3)	−0.001 (3)	−0.009 (3)
C26	0.067 (3)	0.077 (3)	0.091 (4)	−0.005 (3)	0.007 (3)	−0.029 (3)
C27	0.054 (3)	0.045 (2)	0.055 (3)	−0.0123 (19)	−0.002 (2)	−0.0082 (19)
C28	0.098 (4)	0.057 (3)	0.070 (3)	−0.017 (3)	−0.005 (3)	0.003 (2)
C29	0.126 (6)	0.063 (3)	0.115 (6)	0.023 (4)	−0.050 (4)	−0.021 (4)
C30	0.070 (4)	0.140 (7)	0.138 (7)	0.022 (4)	−0.027 (4)	−0.082 (6)
C31	0.060 (4)	0.147 (6)	0.093 (4)	−0.035 (4)	0.024 (3)	−0.042 (4)
C32	0.078 (4)	0.064 (3)	0.066 (3)	−0.023 (3)	0.000 (3)	0.003 (2)

Geometric parameters (Å, º)

Zn1—O1	1.964 (2)	C12—H12	0.9300
Zn1—O3	1.987 (2)	C13—C14	1.352 (7)
Zn1—Cl1	2.2303 (12)	C13—H13	0.9300
Zn1—Cl2	2.2178 (11)	C14—C15	1.362 (7)
N1—C2	1.308 (5)	C14—H14	0.9300
N1—C10	1.453 (5)	C15—C16	1.379 (6)
N1—H1	0.9693	C15—H15	0.9300
N2—C18	1.292 (5)	C16—H16	0.9300
N2—C26	1.470 (5)	C17—C18	1.514 (5)
N2—H2	0.9717	C17—H17A	0.9600
O1—C4	1.312 (4)	C17—H17B	0.9600
O2—C6	1.361 (5)	C17—H17C	0.9600
O2—C9	1.438 (5)	C18—C19	1.433 (5)
O3—C20	1.312 (4)	C19—C24	1.412 (5)
O4—C22	1.361 (5)	C19—C20	1.428 (5)
O4—C25	1.411 (5)	C20—C21	1.400 (5)
C1—C2	1.498 (5)	C21—C22	1.361 (5)
C1—H1A	0.9600	C21—H21	0.9300
C1—H1B	0.9600	C22—C23	1.383 (6)
C1—H1C	0.9600	C23—C24	1.348 (6)
C2—C3	1.440 (5)	C23—H23	0.9300
C3—C8	1.418 (5)	C24—H24	0.9300
C3—C4	1.421 (5)	C25—H25A	0.9600
C4—C5	1.398 (5)	C25—H25B	0.9600
C5—C6	1.360 (5)	C25—H25C	0.9600
C5—H5	0.9300	C26—C27	1.501 (6)
C6—C7	1.406 (5)	C26—H26A	0.9700
C7—C8	1.344 (5)	C26—H26B	0.9700
C7—H7	0.9300	C27—C28	1.361 (6)
C8—H8	0.9300	C27—C32	1.365 (6)
C9—H9A	0.9600	C28—C29	1.376 (8)
C9—H9B	0.9600	C28—H28	0.9300
C9—H9C	0.9600	C29—C30	1.353 (9)
C10—C11	1.506 (5)	C29—H29	0.9300
C10—H10A	0.9700	C30—C31	1.354 (9)
C10—H10B	0.9700	C30—H30	0.9300
C11—C16	1.366 (5)	C31—C32	1.361 (7)
C11—C12	1.376 (5)	C31—H31	0.9300
C12—C13	1.375 (6)	C32—H32	0.9300
O1—Zn1—O3	108.13 (10)	C13—C14—H14	120.5
O1—Zn1—Cl2	113.27 (8)	C15—C14—H14	120.5
O3—Zn1—Cl2	102.41 (7)	C14—C15—C16	120.5 (5)
O1—Zn1—Cl1	102.80 (8)	C14—C15—H15	119.8
O3—Zn1—Cl1	110.58 (8)	C16—C15—H15	119.8
Cl1—Zn1—Cl2	119.42 (5)	C11—C16—C15	120.8 (4)
C2—N1—C10	127.3 (3)	C11—C16—H16	119.6
C2—N1—H1	104.2	C15—C16—H16	119.6
C10—N1—H1	128.2	C18—C17—H17A	109.5
C18—N2—C26	129.1 (4)	C18—C17—H17B	109.5
C18—N2—H2	119.2	H17A—C17—H17B	109.5
C26—N2—H2	111.5	C18—C17—H17C	109.5
C4—O1—Zn1	127.9 (2)	H17A—C17—H17C	109.5
C6—O2—C9	117.3 (4)	H17B—C17—H17C	109.5
C20—O3—Zn1	126.8 (2)	N2—C18—C19	119.7 (3)
C22—O4—C25	118.5 (3)	N2—C18—C17	119.1 (4)
C2—C1—H1A	109.5	C19—C18—C17	121.2 (4)
C2—C1—H1B	109.5	C24—C19—C20	116.8 (4)
H1A—C1—H1B	109.5	C24—C19—C18	121.2 (4)
C2—C1—H1C	109.5	C20—C19—C18	122.0 (3)
H1A—C1—H1C	109.5	O3—C20—C21	120.9 (3)
H1B—C1—H1C	109.5	O3—C20—C19	120.1 (3)
N1—C2—C3	119.4 (3)	C21—C20—C19	119.0 (3)
N1—C2—C1	118.7 (4)	C22—C21—C20	121.1 (4)
C3—C2—C1	121.9 (4)	C22—C21—H21	119.4
C8—C3—C4	117.3 (4)	C20—C21—H21	119.4
C8—C3—C2	120.9 (3)	C21—C22—O4	124.4 (4)
C4—C3—C2	121.8 (3)	C21—C22—C23	120.6 (4)
O1—C4—C5	120.4 (3)	O4—C22—C23	115.0 (4)
O1—C4—C3	120.6 (3)	C24—C23—C22	119.7 (4)
C5—C4—C3	118.9 (4)	C24—C23—H23	120.2
C6—C5—C4	121.4 (4)	C22—C23—H23	120.2
C6—C5—H5	119.3	C23—C24—C19	122.8 (4)
C4—C5—H5	119.3	C23—C24—H24	118.6
C5—C6—O2	124.5 (4)	C19—C24—H24	118.6
C5—C6—C7	120.5 (4)	O4—C25—H25A	109.5
O2—C6—C7	114.9 (4)	O4—C25—H25B	109.5
C8—C7—C6	119.0 (4)	H25A—C25—H25B	109.5
C8—C7—H7	120.5	O4—C25—H25C	109.5
C6—C7—H7	120.5	H25A—C25—H25C	109.5
C7—C8—C3	122.8 (4)	H25B—C25—H25C	109.5
C7—C8—H8	118.6	N2—C26—C27	110.6 (3)
C3—C8—H8	118.6	N2—C26—H26A	109.5
O2—C9—H9A	109.5	C27—C26—H26A	109.5
O2—C9—H9B	109.5	N2—C26—H26B	109.5
H9A—C9—H9B	109.5	C27—C26—H26B	109.5
O2—C9—H9C	109.5	H26A—C26—H26B	108.1
H9A—C9—H9C	109.5	C28—C27—C32	118.8 (4)
H9B—C9—H9C	109.5	C28—C27—C26	120.8 (4)
N1—C10—C11	113.7 (3)	C32—C27—C26	120.5 (4)
N1—C10—H10A	108.8	C27—C28—C29	120.7 (5)
C11—C10—H10A	108.8	C27—C28—H28	119.6
N1—C10—H10B	108.8	C29—C28—H28	119.6
C11—C10—H10B	108.8	C30—C29—C28	119.4 (6)
H10A—C10—H10B	107.7	C30—C29—H29	120.3
C16—C11—C12	118.3 (4)	C28—C29—H29	120.3
C16—C11—C10	122.3 (4)	C29—C30—C31	120.3 (7)
C12—C11—C10	119.4 (4)	C29—C30—H30	119.9
C13—C12—C11	120.2 (4)	C31—C30—H30	119.9
C13—C12—H12	119.9	C30—C31—C32	120.2 (6)
C11—C12—H12	119.9	C30—C31—H31	119.9
C14—C13—C12	121.3 (5)	C32—C31—H31	119.9
C14—C13—H13	119.4	C31—C32—C27	120.6 (5)
C12—C13—H13	119.4	C31—C32—H32	119.7
C13—C14—C15	118.9 (5)	C27—C32—H32	119.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.97	1.63	2.543 (4)	156
N2—H2···O3	0.97	1.77	2.545 (4)	134