Bis(1-aceto­phenone-1H-benzotriazole-κN³)­di­chloro­zinc(II)

In the title compound, [ZnCl₂(C₆H₄N₃CH₂COPh)₂], the zinc ion is coordinated by two Cl⁻ anions and two N atoms of two triazole ligands, forming a distorted tetrahedral geometry. The molecular structure and packing are stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O2     ..  C7       =       2.91 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A   ..  CL2      =       2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A   ..  CL1      =       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A   ..  CL1      =       2.88 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C6     ..  O1       =      98.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C24    ..  O2       =      98.00 Deg.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   2 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: R-AXIS Software (Rigaku, 1997); cell refinement: R-AXIS Software; data reduction: R-AXIS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

[ZnCl2(C14H11N3O)2]	Z = 2
Mr = 610.79	F(000) = 624
Triclinic, P1	Dx = 1.507 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4490 (19) Å	Cell parameters from 20 reflections
b = 11.291 (2) Å	θ = 2–11°
c = 13.637 (3) Å	µ = 1.15 mm^−1
α = 111.70 (3)°	T = 293 K
β = 94.33 (3)°	Pillar, colorless
γ = 90.97 (3)°	0.35 × 0.25 × 0.15 mm
V = 1346.4 (6) Å^3

Data collection

Oxford Instruments point-detector diffractometer	2798 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.3°, θmin = 1.6°
θ/2θ scans	h = 0→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.714, Tmax = 0.842	l = −16→16
5045 measured reflections	3 standard reflections every 100 reflections
4729 independent reflections	intensity decay: none

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 0.4269P] where P = (Fo^2 + 2Fc^2)/3
4729 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.35 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
Zn1	0.25767 (6)	0.62197 (5)	0.81639 (4)	0.03612 (18)
Cl1	0.32563 (14)	0.82640 (12)	0.88646 (10)	0.0492 (4)
Cl2	0.38214 (14)	0.47816 (13)	0.85451 (10)	0.0503 (4)
O1	0.2345 (4)	0.8218 (3)	0.5129 (3)	0.0544 (10)
O2	−0.2765 (4)	0.3802 (3)	0.7196 (2)	0.0486 (9)
N1	0.1398 (4)	0.5968 (4)	0.5143 (3)	0.0403 (10)
N2	0.1401 (4)	0.6420 (4)	0.6196 (3)	0.0423 (10)
N3	0.2291 (4)	0.5764 (4)	0.6552 (3)	0.0398 (10)
N4	0.0548 (4)	0.6058 (3)	0.8587 (3)	0.0361 (9)
N5	0.0088 (4)	0.4966 (4)	0.8626 (3)	0.0400 (10)
N6	−0.1208 (4)	0.5132 (4)	0.8964 (3)	0.0359 (9)
C1	0.0550 (6)	0.8425 (5)	0.3883 (4)	0.0447 (13)
C2	−0.0672 (6)	0.7898 (5)	0.3224 (4)	0.0541 (15)
H2B	−0.1089	0.7141	0.3214	0.065*
C3	−0.1277 (7)	0.8490 (7)	0.2581 (5)	0.078 (2)
H3A	−0.2094	0.8128	0.2138	0.093*
C4	−0.0676 (8)	0.9604 (8)	0.2596 (6)	0.088 (2)
H4A	−0.1089	0.9997	0.2162	0.106*
C5	0.0534 (8)	1.0153 (6)	0.3245 (6)	0.081 (2)
H5B	0.0938	1.0913	0.3251	0.097*
C6	0.1145 (6)	0.9562 (5)	0.3891 (4)	0.0558 (15)
H6A	0.1961	0.9931	0.4333	0.067*
C7	0.1273 (5)	0.7808 (5)	0.4573 (4)	0.0401 (12)
C8	0.0547 (5)	0.6562 (5)	0.4537 (4)	0.0438 (13)
H8A	−0.0371	0.6742	0.4820	0.053*
H8B	0.0389	0.5974	0.3807	0.053*
C9	0.2294 (5)	0.4991 (4)	0.4792 (3)	0.0347 (11)
C10	0.2634 (6)	0.4192 (5)	0.3789 (4)	0.0512 (14)
H10A	0.2236	0.4267	0.3171	0.061*
C11	0.3587 (7)	0.3298 (5)	0.3777 (4)	0.0655 (18)
H11A	0.3835	0.2737	0.3126	0.079*
C12	0.4216 (7)	0.3185 (6)	0.4708 (4)	0.0677 (18)
H12A	0.4877	0.2567	0.4653	0.081*
C13	0.3876 (6)	0.3959 (5)	0.5688 (4)	0.0529 (15)
H13A	0.4289	0.3884	0.6302	0.063*
C14	0.2878 (5)	0.4872 (4)	0.5724 (3)	0.0379 (12)
C15	−0.0475 (5)	0.6938 (4)	0.8906 (3)	0.0339 (11)
C16	−0.0514 (6)	0.8201 (5)	0.8978 (4)	0.0493 (14)
H16A	0.0248	0.8610	0.8819	0.059*
C17	−0.1736 (6)	0.8803 (5)	0.9295 (5)	0.0635 (17)
H17A	−0.1806	0.9647	0.9355	0.076*
C18	−0.2884 (6)	0.8191 (6)	0.9533 (5)	0.0667 (18)
H18A	−0.3689	0.8646	0.9750	0.080*
C19	−0.2871 (5)	0.6954 (5)	0.9460 (4)	0.0535 (15)
H19A	−0.3640	0.6550	0.9615	0.064*
C20	−0.1628 (5)	0.6338 (4)	0.9137 (3)	0.0349 (11)
C21	−0.2042 (5)	0.4034 (4)	0.8955 (4)	0.0414 (12)
H21A	−0.2695	0.4310	0.9503	0.050*
H21B	−0.1415	0.3441	0.9108	0.050*
C22	−0.2876 (5)	0.3364 (4)	0.7882 (3)	0.0342 (11)
C23	−0.3740 (5)	0.2190 (4)	0.7702 (3)	0.0336 (11)
C24	−0.4478 (5)	0.1574 (5)	0.6714 (4)	0.0426 (13)
H24A	−0.4425	0.1908	0.6188	0.051*
C25	−0.5278 (5)	0.0483 (5)	0.6517 (4)	0.0517 (14)
H25A	−0.5770	0.0074	0.5855	0.062*
C26	−0.5363 (5)	−0.0020 (5)	0.7290 (4)	0.0520 (15)
H26A	−0.5921	−0.0759	0.7154	0.062*
C27	−0.4624 (6)	0.0570 (5)	0.8259 (4)	0.0558 (15)
H27A	−0.4665	0.0219	0.8776	0.067*
C28	−0.3824 (5)	0.1673 (5)	0.8475 (4)	0.0467 (13)
H28A	−0.3338	0.2077	0.9139	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0360 (4)	0.0399 (4)	0.0339 (3)	−0.0018 (3)	0.0035 (2)	0.0154 (3)
Cl1	0.0505 (8)	0.0420 (8)	0.0536 (8)	−0.0127 (7)	−0.0003 (6)	0.0174 (6)
Cl2	0.0497 (8)	0.0571 (9)	0.0529 (8)	0.0131 (7)	0.0080 (6)	0.0295 (7)
O1	0.054 (2)	0.052 (2)	0.054 (2)	−0.016 (2)	−0.0125 (19)	0.0198 (19)
O2	0.068 (3)	0.044 (2)	0.038 (2)	−0.0156 (19)	0.0003 (17)	0.0225 (17)
N1	0.043 (3)	0.045 (3)	0.037 (2)	−0.003 (2)	−0.005 (2)	0.021 (2)
N2	0.044 (3)	0.051 (3)	0.037 (2)	0.003 (2)	0.001 (2)	0.022 (2)
N3	0.041 (3)	0.048 (3)	0.032 (2)	0.003 (2)	0.0019 (19)	0.018 (2)
N4	0.035 (2)	0.031 (2)	0.041 (2)	−0.002 (2)	0.0042 (18)	0.0120 (19)
N5	0.041 (3)	0.035 (2)	0.040 (2)	−0.002 (2)	0.006 (2)	0.0095 (19)
N6	0.033 (2)	0.038 (2)	0.038 (2)	−0.005 (2)	0.0044 (18)	0.0150 (19)
C1	0.050 (3)	0.042 (3)	0.045 (3)	0.013 (3)	0.016 (3)	0.016 (3)
C2	0.057 (4)	0.056 (4)	0.057 (3)	0.013 (3)	0.001 (3)	0.030 (3)
C3	0.073 (5)	0.090 (5)	0.082 (5)	0.021 (4)	−0.010 (4)	0.048 (4)
C4	0.097 (6)	0.102 (6)	0.099 (6)	0.027 (5)	0.015 (5)	0.075 (5)
C5	0.098 (6)	0.068 (5)	0.104 (6)	0.018 (4)	0.035 (5)	0.059 (4)
C6	0.060 (4)	0.045 (3)	0.067 (4)	0.004 (3)	0.012 (3)	0.025 (3)
C7	0.042 (3)	0.038 (3)	0.037 (3)	0.000 (3)	0.005 (2)	0.010 (2)
C8	0.041 (3)	0.046 (3)	0.049 (3)	−0.005 (3)	−0.010 (2)	0.024 (3)
C9	0.040 (3)	0.031 (3)	0.033 (3)	−0.007 (2)	0.000 (2)	0.014 (2)
C10	0.075 (4)	0.046 (3)	0.037 (3)	−0.001 (3)	0.002 (3)	0.022 (3)
C11	0.107 (5)	0.054 (4)	0.032 (3)	0.019 (4)	0.014 (3)	0.010 (3)
C12	0.096 (5)	0.067 (4)	0.044 (3)	0.031 (4)	0.014 (3)	0.024 (3)
C13	0.069 (4)	0.055 (4)	0.040 (3)	0.016 (3)	0.005 (3)	0.023 (3)
C14	0.046 (3)	0.038 (3)	0.033 (3)	−0.002 (3)	0.004 (2)	0.017 (2)
C15	0.027 (3)	0.038 (3)	0.036 (3)	−0.001 (2)	0.000 (2)	0.013 (2)
C16	0.041 (3)	0.036 (3)	0.070 (4)	−0.004 (3)	0.001 (3)	0.020 (3)
C17	0.049 (4)	0.036 (3)	0.096 (5)	0.000 (3)	−0.006 (3)	0.015 (3)
C18	0.032 (3)	0.054 (4)	0.097 (5)	0.007 (3)	0.007 (3)	0.008 (3)
C19	0.035 (3)	0.056 (4)	0.061 (4)	−0.010 (3)	0.009 (3)	0.012 (3)
C20	0.032 (3)	0.036 (3)	0.029 (3)	−0.006 (2)	0.001 (2)	0.005 (2)
C21	0.049 (3)	0.040 (3)	0.039 (3)	−0.012 (3)	0.005 (2)	0.020 (2)
C22	0.038 (3)	0.034 (3)	0.032 (3)	0.004 (2)	0.005 (2)	0.012 (2)
C23	0.034 (3)	0.031 (3)	0.035 (3)	−0.002 (2)	0.002 (2)	0.012 (2)
C24	0.048 (3)	0.041 (3)	0.042 (3)	−0.005 (3)	0.000 (2)	0.020 (2)
C25	0.053 (4)	0.047 (3)	0.047 (3)	−0.015 (3)	−0.006 (3)	0.012 (3)
C26	0.053 (4)	0.037 (3)	0.060 (4)	−0.017 (3)	0.008 (3)	0.011 (3)
C27	0.064 (4)	0.054 (4)	0.055 (4)	−0.012 (3)	0.010 (3)	0.028 (3)
C28	0.054 (3)	0.050 (3)	0.039 (3)	−0.012 (3)	−0.004 (2)	0.022 (3)

Geometric parameters (Å, º)

Zn1—N3	2.059 (4)	C10—C11	1.360 (7)
Zn1—N4	2.068 (4)	C10—H10A	0.9300
Zn1—Cl1	2.2089 (15)	C11—C12	1.411 (7)
Zn1—Cl2	2.2106 (15)	C11—H11A	0.9300
O1—C7	1.193 (5)	C12—C13	1.365 (7)
O2—C22	1.219 (5)	C12—H12A	0.9300
N1—N2	1.334 (5)	C13—C14	1.399 (6)
N1—C9	1.366 (6)	C13—H13A	0.9300
N1—C8	1.451 (5)	C15—C20	1.389 (6)
N2—N3	1.310 (5)	C15—C16	1.394 (6)
N3—C14	1.366 (6)	C16—C17	1.367 (7)
N4—N5	1.321 (5)	C16—H16A	0.9300
N4—C15	1.373 (5)	C17—C18	1.397 (7)
N5—N6	1.332 (5)	C17—H17A	0.9300
N6—C20	1.365 (6)	C18—C19	1.363 (7)
N6—C21	1.454 (5)	C18—H18A	0.9300
C1—C2	1.386 (7)	C19—C20	1.391 (7)
C1—C6	1.389 (7)	C19—H19A	0.9300
C1—C7	1.497 (7)	C21—C22	1.523 (6)
C2—C3	1.383 (7)	C21—H21A	0.9700
C2—H2B	0.9300	C21—H21B	0.9700
C3—C4	1.364 (9)	C22—C23	1.475 (6)
C3—H3A	0.9300	C23—C28	1.386 (6)
C4—C5	1.376 (9)	C23—C24	1.391 (6)
C4—H4A	0.9300	C24—C25	1.362 (6)
C5—C6	1.387 (7)	C24—H24A	0.9300
C5—H5B	0.9300	C25—C26	1.376 (7)
C6—H6A	0.9300	C25—H25A	0.9300
C7—C8	1.537 (6)	C26—C27	1.368 (7)
C8—H8A	0.9700	C26—H26A	0.9300
C8—H8B	0.9700	C27—C28	1.368 (6)
C9—C10	1.397 (6)	C27—H27A	0.9300
C9—C14	1.400 (6)	C28—H28A	0.9300
N3—Zn1—N4	103.87 (15)	C12—C11—H11A	118.5
N3—Zn1—Cl1	106.12 (12)	C13—C12—C11	121.6 (5)
N4—Zn1—Cl1	107.07 (11)	C13—C12—H12A	119.2
N3—Zn1—Cl2	111.06 (12)	C11—C12—H12A	119.2
N4—Zn1—Cl2	106.56 (11)	C12—C13—C14	116.8 (5)
Cl1—Zn1—Cl2	120.85 (6)	C12—C13—H13A	121.6
N2—N1—C9	111.6 (4)	C14—C13—H13A	121.6
N2—N1—C8	119.5 (4)	N3—C14—C13	131.8 (4)
C9—N1—C8	128.9 (4)	N3—C14—C9	107.4 (4)
N3—N2—N1	107.4 (4)	C13—C14—C9	120.7 (4)
N2—N3—C14	109.9 (4)	N4—C15—C20	107.6 (4)
N2—N3—Zn1	118.0 (3)	N4—C15—C16	131.2 (4)
C14—N3—Zn1	132.1 (3)	C20—C15—C16	121.2 (5)
N5—N4—C15	109.2 (4)	C17—C16—C15	116.1 (5)
N5—N4—Zn1	119.4 (3)	C17—C16—H16A	121.9
C15—N4—Zn1	131.3 (3)	C15—C16—H16A	121.9
N4—N5—N6	107.4 (4)	C16—C17—C18	122.1 (5)
N5—N6—C20	111.5 (4)	C16—C17—H17A	118.9
N5—N6—C21	119.1 (4)	C18—C17—H17A	118.9
C20—N6—C21	128.7 (4)	C19—C18—C17	122.6 (5)
C2—C1—C6	118.7 (5)	C19—C18—H18A	118.7
C2—C1—C7	122.8 (5)	C17—C18—H18A	118.7
C6—C1—C7	118.5 (5)	C18—C19—C20	115.4 (5)
C3—C2—C1	120.5 (6)	C18—C19—H19A	122.3
C3—C2—H2B	119.8	C20—C19—H19A	122.3
C1—C2—H2B	119.8	N6—C20—C15	104.2 (4)
C4—C3—C2	120.1 (6)	N6—C20—C19	133.3 (5)
C4—C3—H3A	119.9	C15—C20—C19	122.5 (5)
C2—C3—H3A	119.9	N6—C21—C22	110.8 (4)
C3—C4—C5	120.8 (6)	N6—C21—H21A	109.5
C3—C4—H4A	119.6	C22—C21—H21A	109.5
C5—C4—H4A	119.6	N6—C21—H21B	109.5
C4—C5—C6	119.3 (6)	C22—C21—H21B	109.5
C4—C5—H5B	120.3	H21A—C21—H21B	108.1
C6—C5—H5B	120.3	O2—C22—C23	122.6 (4)
C5—C6—C1	120.7 (6)	O2—C22—C21	118.4 (4)
C5—C6—H6A	119.7	C23—C22—C21	118.9 (4)
C1—C6—H6A	119.7	C28—C23—C24	119.1 (4)
O1—C7—C1	124.5 (5)	C28—C23—C22	122.4 (4)
O1—C7—C8	119.7 (4)	C24—C23—C22	118.5 (4)
C1—C7—C8	115.8 (4)	C25—C24—C23	120.1 (5)
N1—C8—C7	111.8 (4)	C25—C24—H24A	120.0
N1—C8—H8A	109.3	C23—C24—H24A	120.0
C7—C8—H8A	109.3	C24—C25—C26	120.5 (5)
N1—C8—H8B	109.3	C24—C25—H25A	119.8
C7—C8—H8B	109.3	C26—C25—H25A	119.8
H8A—C8—H8B	107.9	C27—C26—C25	119.8 (5)
N1—C9—C10	133.9 (4)	C27—C26—H26A	120.1
N1—C9—C14	103.7 (4)	C25—C26—H26A	120.1
C10—C9—C14	122.4 (5)	C26—C27—C28	120.5 (5)
C11—C10—C9	115.5 (5)	C26—C27—H27A	119.7
C11—C10—H10A	122.2	C28—C27—H27A	119.7
C9—C10—H10A	122.2	C27—C28—C23	120.0 (5)
C10—C11—C12	122.9 (5)	C27—C28—H28A	120.0
C10—C11—H11A	118.5	C23—C28—H28A	120.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.56	2.846 (8)	98
C13—H13A···Cl2	0.93	2.92	3.661 (6)	138
C16—H16A···Cl1	0.93	2.88	3.578 (6)	133
C24—H24A···O2	0.93	2.51	2.803 (6)	98
C10—H10A···O2^i	0.93	2.46	3.036 (7)	120
C21—H21A···Cl2^ii	0.97	2.78	3.716 (5)	163
C28—H28A···Cl1^ii	0.92	2.88	3.601 (6)	135

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