catena-Poly[dipropyl­ammonium [[bis­(benzotriazolato-κN1)zinc(II)]-μ-benzotriazolato-κ2N1:N3]]

Xu, L.

doi:10.1107/S160053680902563X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m884

doi:10.1107/S160053680902563X

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catena-Poly[dipropylammonium [[bis(benzotriazolato-κN¹)zinc(II)]-μ-benzotriazolato-κ²N¹:N³]]

Liping Xu ^a ^*

^aCollege of Science and Information, Qingdao Agricultural University, No. 700 Changcheng Road, Chengyang, Qingdao 266109, People's Republic of China
^*Correspondence e-mail: xu_li_ping@yeah.net

(Received 8 June 2009; accepted 2 July 2009; online 8 July 2009)

In the title compound, {(C₆H₁₆N)[Zn(C₆H₄N₃)₃]}_n, the Zn^II atom has a distorted tetrahedral geometry defined by four N atoms from four benzotriazolate (BTA) ligands. The compound is composed of extended polymeric chains in which two BTA N atoms bridge [Zn(BTA)₂] fragments along [001]. Cations and anions are linked by N—H⋯N hydrogen-bond interactions along [010].

Related literature

For background information on the design and synthesis of supramolecular complexes: see Yaghi et al. (1998 ); Shao et al. (2008 ).

Experimental

Crystal data

(C₆H₁₆N)[Zn(C₆H₄N₃)₃]
M_r = 521.93
Monoclinic, P 2₁ /c
a = 11.9439 (15) Å
b = 9.8058 (13) Å
c = 21.585 (3) Å
β = 104.212 (2)°
V = 2450.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.286, T_max = 0.322 (expected range = 0.835–0.940)
11639 measured reflections
4107 independent reflections
2645 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.095
S = 0.96
4107 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Zn1ⁱ	2.000 (3)
N3—Zn1	1.990 (3)
N6—Zn1	1.982 (3)
Zn1—N1ⁱⁱ	2.000 (3)

N6—Zn1—N1ⁱⁱ	106.15 (12)
N9—Zn1—N1ⁱⁱ	111.79 (12)
N3—Zn1—N1ⁱⁱ	113.61 (12)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H27⋯N7	0.90	1.96	2.824 (4)	160
N10—H27⋯N8	0.90	2.42	3.052 (4)	127
N10—H26⋯N4ⁱⁱⁱ	0.90	1.93	2.821 (4)	171
Symmetry code: (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902563X/bx2217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902563X/bx2217Isup2.hkl

checkCIF report

Comment top

In the research of supramolecular chemistry, a great interest has recently been focused on the crystal engineering of coordination frameworks due to their intriguing architectures, new topologies, intertwining phenomena and potential applications in microelectronics, nonlinear optics, ion exchange, molecular selection, molecular separation and recognition (Yaghi et al., 1998). Shao et al. report the first example of chiral [Zn(BTA)₂] with a bikitaite (BIK) zeolitic topology, was successfully isolated under hydrothermal conditions (Shao et al., 2008). Here, we report the crystal and molecular structure of {[DPAH][Zn(BTA)₃]}_n , (I), Fig. 1 (DPAH=dipropylammonium, BTA = benzotriazolate).The Zn atom has a distorted tetrahedral geometry, defined by four N atoms from four BTA ligands. The BTA behaves as a monodentate ligand.The material is composed of one-dimensional extended polymeric chains in which two N atoms from benzotriazolate anion bridges fragment of Zn(BTA)₂in [0 0 1] direction. The cations and anions are linked by N-H···N hydrogen bond interaction in the [0 1 0 ] direction.

Related literature top

For background information on the design and synthesis of supramolecular complexes: see Yaghi et al. (1998); Shao et al. (2008).

Experimental top

A mixture of Zn(NO₃)₂. 6H₂O (0.149 g, 0.5 mmol), BTAH (0.119 g, 1.0 mmol) in 3.0 ml DPA solution was stirred for 30 min in a 17.0 ml Teflon-lined stainless steel. The vessel was sealed and heated at 190 °C for one week. The orange block crystals were isolated by washing with ethanol and water.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of I. Displacement ellipsoids are drawn at the 30% probability level and all H atoms have been omitted for clarity.

catena-Poly[dipropylammonium [[bis(benzotriazolato-κN¹)zinc(II)]-µ- benzotriazolato-κ²N¹:N³]] top

Crystal data top

(C₆H₁₆N)[Zn(C₆H₄N₃)₃]	F(000) = 1088
M_r = 521.93	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12055 reflections
a = 11.9439 (15) Å	θ = 2.0–24.6°
b = 9.8058 (13) Å	µ = 1.04 mm⁻¹
c = 21.585 (3) Å	T = 293 K
β = 104.212 (2)°	Plate, white
V = 2450.7 (5) Å³	0.35 × 0.2 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4107 independent reflections
Radiation source: fine-focus sealed tube	2645 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 24.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.286, T_max = 0.322	k = −11→11
11639 measured reflections	l = −14→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0376P)²] where P = (F_o² + 2F_c²)/3
4107 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

(C₆H₁₆N)[Zn(C₆H₄N₃)₃]	V = 2450.7 (5) Å³
M_r = 521.93	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9439 (15) Å	µ = 1.04 mm⁻¹
b = 9.8058 (13) Å	T = 293 K
c = 21.585 (3) Å	0.35 × 0.2 × 0.06 mm
β = 104.212 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4107 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2645 reflections with I > 2σ(I)
T_min = 0.286, T_max = 0.322	R_int = 0.075
11639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 0.96	Δρ_max = 0.53 e Å⁻³
4107 reflections	Δρ_min = −0.54 e Å⁻³
316 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6479 (3)	0.3188 (4)	0.83315 (16)	0.0186 (9)
C2	0.7447 (3)	0.3069 (4)	0.88465 (17)	0.0261 (10)
H2	0.7856	0.2256	0.8936	0.031*
C3	0.7760 (4)	0.4204 (4)	0.92092 (18)	0.0299 (10)
H3	0.8402	0.4166	0.9554	0.036*
C4	0.7145 (3)	0.5429 (4)	0.90794 (17)	0.0315 (10)
H4	0.7387	0.6179	0.9342	0.038*
C5	0.6201 (3)	0.5554 (4)	0.85786 (17)	0.0279 (10)
H5	0.5793	0.6368	0.8493	0.033*
C6	0.5877 (3)	0.4396 (4)	0.81994 (17)	0.0199 (9)
C7	0.1821 (3)	0.4217 (3)	0.60887 (17)	0.0204 (9)
C8	0.0800 (4)	0.4131 (4)	0.6293 (2)	0.0325 (10)
H8	0.0773	0.4388	0.6704	0.039*
C9	−0.0156 (4)	0.3656 (4)	0.5864 (2)	0.0380 (11)
H9	−0.0846	0.3580	0.5988	0.046*
C10	−0.0127 (4)	0.3280 (4)	0.5245 (2)	0.0388 (11)
H10	−0.0800	0.2968	0.4966	0.047*
C11	0.0852 (4)	0.3356 (4)	0.50407 (19)	0.0333 (11)
H11	0.0866	0.3100	0.4628	0.040*
C12	0.1840 (3)	0.3832 (4)	0.54704 (17)	0.0242 (9)
C13	0.1248 (3)	0.4877 (4)	0.83554 (17)	0.0255 (10)
C14	0.1554 (3)	0.5604 (4)	0.78660 (17)	0.0244 (10)
C15	0.0800 (4)	0.6553 (4)	0.75005 (18)	0.0314 (10)
H15	0.1003	0.7054	0.7179	0.038*
C16	−0.0249 (4)	0.6710 (4)	0.7637 (2)	0.0400 (12)
H16	−0.0774	0.7330	0.7402	0.048*
C17	−0.0556 (4)	0.5959 (5)	0.8124 (2)	0.0418 (12)
H17	−0.1284	0.6087	0.8198	0.050*
C18	0.0170 (3)	0.5059 (4)	0.84886 (19)	0.0346 (11)
H18	−0.0037	0.4579	0.8815	0.042*
C19	0.2867 (4)	−0.0562 (4)	0.8168 (2)	0.0502 (13)
H20	0.2170	−0.1089	0.8047	0.075*
H21	0.3514	−0.1161	0.8313	0.075*
H19	0.2968	−0.0051	0.7806	0.075*
C20	0.2788 (3)	0.0409 (4)	0.86994 (18)	0.0338 (10)
H23	0.2128	0.1006	0.8552	0.041*
H22	0.2664	−0.0109	0.9060	0.041*
C21	0.3860 (3)	0.1259 (4)	0.89145 (18)	0.0282 (10)
H24	0.4518	0.0673	0.9085	0.034*
H25	0.4006	0.1756	0.8554	0.034*
C22	0.4728 (3)	0.3076 (4)	0.97182 (18)	0.0310 (10)
H28	0.4487	0.3792	0.9967	0.037*
H29	0.5027	0.3506	0.9388	0.037*
C23	0.5670 (4)	0.2259 (4)	1.0144 (2)	0.0379 (11)
H31	0.6029	0.1676	0.9885	0.045*
H30	0.5343	0.1681	1.0419	0.045*
C24	0.6569 (4)	0.3179 (4)	1.0548 (2)	0.0414 (12)
H33	0.7161	0.2636	1.0818	0.062*
H32	0.6215	0.3751	1.0807	0.062*
H34	0.6905	0.3738	1.0275	0.062*
N1	0.5952 (3)	0.2264 (3)	0.78762 (14)	0.0210 (7)
N2	0.5060 (3)	0.2896 (3)	0.74886 (15)	0.0219 (7)
N3	0.5003 (3)	0.4185 (3)	0.76708 (14)	0.0211 (8)
N4	0.2938 (3)	0.4007 (3)	0.54137 (14)	0.0290 (8)
N5	0.3569 (3)	0.4464 (3)	0.59662 (15)	0.0283 (8)
N6	0.2912 (2)	0.4601 (3)	0.63867 (13)	0.0214 (7)
N7	0.2144 (3)	0.4034 (3)	0.86208 (15)	0.0284 (8)
N8	0.2947 (3)	0.4209 (3)	0.82976 (14)	0.0279 (8)
N9	0.2615 (3)	0.5154 (3)	0.78374 (14)	0.0229 (7)
N10	0.3708 (3)	0.2231 (3)	0.94134 (14)	0.0259 (8)
H26	0.3495	0.1755	0.9722	0.031*
H27	0.3122	0.2795	0.9238	0.031*
Zn1	0.36481 (4)	0.53198 (4)	0.72486 (2)	0.02055 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (2)	0.019 (2)	0.014 (2)	−0.0020 (18)	0.0035 (17)	0.0010 (17)
C2	0.032 (2)	0.023 (2)	0.020 (2)	0.005 (2)	−0.0017 (19)	−0.0009 (18)
C3	0.035 (3)	0.028 (2)	0.021 (2)	0.004 (2)	−0.004 (2)	0.0037 (19)
C4	0.041 (3)	0.028 (2)	0.020 (2)	−0.006 (2)	−0.002 (2)	−0.005 (2)
C5	0.032 (2)	0.025 (3)	0.025 (2)	0.001 (2)	0.0039 (19)	0.0051 (19)
C6	0.024 (2)	0.019 (2)	0.014 (2)	−0.0004 (18)	0.0005 (17)	0.0008 (16)
C7	0.026 (2)	0.017 (2)	0.015 (2)	−0.0019 (18)	−0.0014 (18)	0.0017 (16)
C8	0.036 (3)	0.032 (3)	0.028 (2)	−0.004 (2)	0.005 (2)	−0.0056 (19)
C9	0.023 (3)	0.045 (3)	0.044 (3)	−0.006 (2)	0.003 (2)	−0.004 (2)
C10	0.035 (3)	0.034 (3)	0.035 (3)	−0.006 (2)	−0.015 (2)	−0.009 (2)
C11	0.043 (3)	0.030 (3)	0.020 (2)	−0.001 (2)	−0.006 (2)	−0.0049 (19)
C12	0.030 (3)	0.019 (2)	0.020 (2)	−0.0021 (19)	−0.0008 (19)	0.0009 (18)
C13	0.031 (2)	0.021 (2)	0.024 (2)	−0.0039 (19)	0.0065 (19)	−0.0049 (18)
C14	0.029 (2)	0.024 (2)	0.018 (2)	−0.0020 (19)	0.0011 (19)	−0.0032 (17)
C15	0.039 (3)	0.035 (3)	0.019 (2)	0.002 (2)	0.006 (2)	−0.0032 (19)
C16	0.038 (3)	0.042 (3)	0.035 (3)	0.008 (2)	0.001 (2)	−0.003 (2)
C17	0.032 (3)	0.047 (3)	0.047 (3)	0.004 (2)	0.011 (2)	−0.010 (2)
C18	0.036 (3)	0.040 (3)	0.033 (3)	0.000 (2)	0.016 (2)	−0.002 (2)
C19	0.054 (3)	0.056 (3)	0.042 (3)	0.000 (3)	0.015 (3)	−0.010 (3)
C20	0.036 (3)	0.041 (3)	0.024 (2)	−0.002 (2)	0.007 (2)	−0.007 (2)
C21	0.034 (3)	0.031 (2)	0.022 (2)	0.006 (2)	0.010 (2)	0.0035 (19)
C22	0.037 (3)	0.028 (2)	0.028 (2)	−0.005 (2)	0.007 (2)	−0.001 (2)
C23	0.036 (3)	0.035 (3)	0.039 (3)	−0.004 (2)	0.002 (2)	−0.002 (2)
C24	0.040 (3)	0.044 (3)	0.037 (3)	−0.005 (2)	0.002 (2)	−0.001 (2)
N1	0.0237 (19)	0.0212 (18)	0.0172 (18)	0.0012 (15)	0.0033 (15)	0.0035 (14)
N2	0.0254 (18)	0.0170 (17)	0.0217 (17)	0.0012 (14)	0.0028 (14)	0.0005 (14)
N3	0.028 (2)	0.0172 (18)	0.0177 (18)	−0.0031 (15)	0.0058 (15)	−0.0024 (14)
N4	0.038 (2)	0.032 (2)	0.0156 (18)	−0.0014 (17)	0.0039 (17)	−0.0031 (15)
N5	0.030 (2)	0.033 (2)	0.0221 (18)	−0.0009 (17)	0.0077 (16)	−0.0014 (16)
N6	0.0252 (18)	0.0213 (17)	0.0174 (17)	−0.0031 (16)	0.0047 (14)	−0.0004 (15)
N7	0.035 (2)	0.029 (2)	0.0232 (19)	0.0002 (17)	0.0106 (17)	0.0042 (16)
N8	0.034 (2)	0.030 (2)	0.0195 (18)	0.0002 (16)	0.0051 (16)	0.0053 (15)
N9	0.0264 (19)	0.0230 (18)	0.0184 (17)	0.0024 (16)	0.0038 (14)	−0.0006 (15)
N10	0.031 (2)	0.0256 (19)	0.0213 (19)	0.0012 (16)	0.0062 (16)	0.0054 (15)
Zn1	0.0255 (3)	0.0186 (2)	0.0158 (2)	−0.0003 (2)	0.00162 (18)	−0.0001 (2)

Geometric parameters (Å, º) top

C1—N1	1.370 (4)	C19—H20	0.9600
C1—C6	1.379 (5)	C19—H21	0.9600
C1—C2	1.398 (5)	C19—H19	0.9600
C2—C3	1.359 (5)	C20—C21	1.503 (5)
C2—H2	0.9300	C20—H23	0.9700
C3—C4	1.400 (5)	C20—H22	0.9700
C3—H3	0.9300	C21—N10	1.482 (4)
C4—C5	1.362 (5)	C21—H24	0.9700
C4—H4	0.9300	C21—H25	0.9700
C5—C6	1.398 (5)	C22—N10	1.486 (4)
C5—H5	0.9300	C22—C23	1.498 (5)
C6—N3	1.360 (4)	C22—H28	0.9700
C7—N6	1.357 (4)	C22—H29	0.9700
C7—C12	1.392 (5)	C23—C24	1.505 (5)
C7—C8	1.398 (5)	C23—H31	0.9700
C8—C9	1.362 (5)	C23—H30	0.9700
C8—H8	0.9300	C24—H33	0.9600
C9—C10	1.396 (5)	C24—H32	0.9600
C9—H9	0.9300	C24—H34	0.9600
C10—C11	1.350 (6)	N1—N2	1.334 (4)
C10—H10	0.9300	N1—Zn1ⁱ	2.000 (3)
C11—C12	1.390 (5)	N2—N3	1.331 (4)
C11—H11	0.9300	N3—Zn1	1.990 (3)
C12—N4	1.357 (5)	N4—N5	1.323 (4)
C13—N7	1.362 (5)	N5—N6	1.345 (4)
C13—N7	1.362 (5)	N6—Zn1	1.982 (3)
C13—C14	1.396 (5)	N7—N7	0.000 (7)
C13—C18	1.398 (5)	N7—N8	1.327 (4)
C14—N9	1.358 (4)	N7—N8	1.327 (4)
C14—C15	1.397 (5)	N8—N8	0.000 (9)
C15—C16	1.364 (5)	N8—N7	1.327 (4)
C15—H15	0.9300	N8—N9	1.345 (4)
C16—C17	1.404 (6)	N9—N8	1.345 (4)
C16—H16	0.9300	N9—Zn1	1.983 (3)
C17—C18	1.347 (5)	N10—H26	0.9000
C17—H17	0.9300	N10—H27	0.9000
C18—H18	0.9300	Zn1—N1ⁱⁱ	2.000 (3)
C19—C20	1.512 (5)

N1—C1—C6	107.2 (3)	H23—C20—H22	107.9
N1—C1—C2	131.3 (3)	N10—C21—C20	109.5 (3)
C6—C1—C2	121.6 (4)	N10—C21—H24	109.8
C3—C2—C1	116.5 (4)	C20—C21—H24	109.8
C3—C2—H2	121.7	N10—C21—H25	109.8
C1—C2—H2	121.7	C20—C21—H25	109.8
C2—C3—C4	122.1 (4)	H24—C21—H25	108.2
C2—C3—H3	119.0	N10—C22—C23	112.6 (3)
C4—C3—H3	119.0	N10—C22—H28	109.1
C5—C4—C3	121.8 (4)	C23—C22—H28	109.1
C5—C4—H4	119.1	N10—C22—H29	109.1
C3—C4—H4	119.1	C23—C22—H29	109.1
C4—C5—C6	116.6 (4)	H28—C22—H29	107.8
C4—C5—H5	121.7	C22—C23—C24	110.9 (4)
C6—C5—H5	121.7	C22—C23—H31	109.5
N3—C6—C1	107.3 (3)	C24—C23—H31	109.5
N3—C6—C5	131.3 (3)	C22—C23—H30	109.5
C1—C6—C5	121.4 (4)	C24—C23—H30	109.5
N6—C7—C12	106.9 (3)	H31—C23—H30	108.1
N6—C7—C8	132.7 (3)	C23—C24—H33	109.5
C12—C7—C8	120.4 (4)	C23—C24—H32	109.5
C9—C8—C7	117.2 (4)	H33—C24—H32	109.5
C9—C8—H8	121.4	C23—C24—H34	109.5
C7—C8—H8	121.4	H33—C24—H34	109.5
C8—C9—C10	121.8 (4)	H32—C24—H34	109.5
C8—C9—H9	119.1	N2—N1—C1	107.3 (3)
C10—C9—H9	119.1	N2—N1—Zn1ⁱ	122.6 (2)
C11—C10—C9	121.7 (4)	C1—N1—Zn1ⁱ	130.1 (2)
C11—C10—H10	119.2	N3—N2—N1	110.3 (3)
C9—C10—H10	119.2	N2—N3—C6	107.9 (3)
C10—C11—C12	117.6 (4)	N2—N3—Zn1	119.4 (2)
C10—C11—H11	121.2	C6—N3—Zn1	132.0 (2)
C12—C11—H11	121.2	N5—N4—C12	108.1 (3)
N4—C12—C11	131.5 (4)	N4—N5—N6	110.2 (3)
N4—C12—C7	107.2 (3)	N5—N6—C7	107.7 (3)
C11—C12—C7	121.3 (4)	N5—N6—Zn1	118.1 (2)
N7—C13—N7	0.0 (3)	C7—N6—Zn1	134.2 (2)
N7—C13—C14	107.7 (3)	N7—N7—N8	0 (10)
N7—C13—C14	107.7 (3)	N7—N7—N8	0 (10)
N7—C13—C18	131.2 (4)	N8—N7—N8	0.00 (19)
N7—C13—C18	131.2 (4)	N7—N7—C13	0 (10)
C14—C13—C18	121.1 (4)	N8—N7—C13	107.1 (3)
N9—C14—C13	106.8 (3)	N8—N7—C13	107.1 (3)
N9—C14—C15	132.2 (4)	N8—N8—N7	0 (10)
C13—C14—C15	121.0 (4)	N8—N8—N7	0 (10)
C16—C15—C14	116.9 (4)	N7—N8—N7	0.0 (3)
C16—C15—H15	121.5	N8—N8—N9	0 (10)
C14—C15—H15	121.5	N7—N8—N9	110.9 (3)
C15—C16—C17	121.7 (4)	N7—N8—N9	110.9 (3)
C15—C16—H16	119.2	N8—N9—N8	0.0 (3)
C17—C16—H16	119.2	N8—N9—C14	107.4 (3)
C18—C17—C16	122.1 (4)	N8—N9—C14	107.4 (3)
C18—C17—H17	118.9	N8—N9—Zn1	114.4 (2)
C16—C17—H17	118.9	N8—N9—Zn1	114.4 (2)
C17—C18—C13	117.2 (4)	C14—N9—Zn1	137.5 (3)
C17—C18—H18	121.4	C21—N10—C22	116.5 (3)
C13—C18—H18	121.4	C21—N10—H26	108.2
C20—C19—H20	109.5	C22—N10—H26	108.2
C20—C19—H21	109.5	C21—N10—H27	108.2
H20—C19—H21	109.5	C22—N10—H27	108.2
C20—C19—H19	109.5	H26—N10—H27	107.3
H20—C19—H19	109.5	N6—Zn1—N9	111.71 (12)
H21—C19—H19	109.5	N6—Zn1—N3	110.77 (12)
C21—C20—C19	112.1 (3)	N9—Zn1—N3	102.96 (12)
C21—C20—H23	109.2	N6—Zn1—N1ⁱⁱ	106.15 (12)
C19—C20—H23	109.2	N9—Zn1—N1ⁱⁱ	111.79 (12)
C21—C20—H22	109.2	N3—Zn1—N1ⁱⁱ	113.61 (12)
C19—C20—H22	109.2

N1—C1—C2—C3	179.1 (4)	C8—C7—N6—N5	178.8 (4)
C6—C1—C2—C3	0.2 (5)	C12—C7—N6—Zn1	178.4 (3)
C1—C2—C3—C4	0.4 (6)	C8—C7—N6—Zn1	−3.1 (6)
C2—C3—C4—C5	−0.4 (6)	C14—C13—N7—N7	0.0 (5)
C3—C4—C5—C6	−0.1 (6)	C18—C13—N7—N7	0.0 (5)
N1—C1—C6—N3	0.0 (4)	N7—C13—N7—N8	0 (100)
C2—C1—C6—N3	179.2 (3)	C14—C13—N7—N8	−1.7 (4)
N1—C1—C6—C5	−179.8 (3)	C18—C13—N7—N8	176.8 (4)
C2—C1—C6—C5	−0.6 (6)	N7—C13—N7—N8	0 (100)
C4—C5—C6—N3	−179.2 (4)	C14—C13—N7—N8	−1.7 (4)
C4—C5—C6—C1	0.6 (5)	C18—C13—N7—N8	176.8 (4)
N6—C7—C8—C9	−178.1 (4)	N7—N7—N8—N8	0.0
C12—C7—C8—C9	0.3 (6)	C13—N7—N8—N8	0.0 (9)
C7—C8—C9—C10	−0.6 (6)	N8—N7—N8—N7	0 (100)
C8—C9—C10—C11	0.6 (7)	C13—N7—N8—N7	0 (100)
C9—C10—C11—C12	−0.3 (6)	N7—N7—N8—N9	0.0 (10)
C10—C11—C12—N4	179.0 (4)	N8—N7—N8—N9	0 (100)
C10—C11—C12—C7	0.0 (6)	C13—N7—N8—N9	1.1 (4)
N6—C7—C12—N4	−0.5 (4)	N7—N8—N9—N8	0 (100)
C8—C7—C12—N4	−179.2 (3)	N7—N8—N9—N8	0 (100)
N6—C7—C12—C11	178.8 (3)	N8—N8—N9—C14	0.0 (9)
C8—C7—C12—C11	0.0 (6)	N7—N8—N9—C14	−0.1 (4)
N7—C13—C14—N9	1.7 (4)	N7—N8—N9—C14	−0.1 (4)
N7—C13—C14—N9	1.7 (4)	N8—N8—N9—Zn1	0.0 (9)
C18—C13—C14—N9	−177.0 (3)	N7—N8—N9—Zn1	−172.1 (2)
N7—C13—C14—C15	179.7 (3)	N7—N8—N9—Zn1	−172.1 (2)
N7—C13—C14—C15	179.7 (3)	C13—C14—N9—N8	−1.0 (4)
C18—C13—C14—C15	1.0 (6)	C15—C14—N9—N8	−178.7 (4)
N9—C14—C15—C16	176.2 (4)	C13—C14—N9—N8	−1.0 (4)
C13—C14—C15—C16	−1.2 (6)	C15—C14—N9—N8	−178.7 (4)
C14—C15—C16—C17	0.3 (6)	C13—C14—N9—Zn1	168.3 (3)
C15—C16—C17—C18	0.9 (7)	C15—C14—N9—Zn1	−9.5 (7)
C16—C17—C18—C13	−1.2 (6)	C20—C21—N10—C22	175.1 (3)
N7—C13—C18—C17	−178.1 (4)	C23—C22—N10—C21	−70.4 (4)
N7—C13—C18—C17	−178.1 (4)	N5—N6—Zn1—N9	−170.4 (2)
C14—C13—C18—C17	0.2 (6)	C7—N6—Zn1—N9	11.7 (4)
C19—C20—C21—N10	177.4 (3)	N5—N6—Zn1—N3	−56.3 (3)
N10—C22—C23—C24	−168.0 (3)	C7—N6—Zn1—N3	125.8 (3)
C6—C1—N1—N2	−0.5 (4)	N5—N6—Zn1—N1ⁱⁱ	67.5 (3)
C2—C1—N1—N2	−179.5 (4)	C7—N6—Zn1—N1ⁱⁱ	−110.4 (3)
C6—C1—N1—Zn1ⁱ	179.0 (2)	N8—N9—Zn1—N6	109.2 (2)
C2—C1—N1—Zn1ⁱ	−0.1 (6)	N8—N9—Zn1—N6	109.2 (2)
C1—N1—N2—N3	0.8 (4)	C14—N9—Zn1—N6	−59.6 (4)
Zn1ⁱ—N1—N2—N3	−178.7 (2)	N8—N9—Zn1—N3	−9.7 (3)
N1—N2—N3—C6	−0.8 (4)	N8—N9—Zn1—N3	−9.7 (3)
N1—N2—N3—Zn1	−172.5 (2)	C14—N9—Zn1—N3	−178.5 (4)
C1—C6—N3—N2	0.5 (4)	N8—N9—Zn1—N1ⁱⁱ	−132.0 (2)
C5—C6—N3—N2	−179.7 (4)	N8—N9—Zn1—N1ⁱⁱ	−132.0 (2)
C1—C6—N3—Zn1	170.8 (2)	C14—N9—Zn1—N1ⁱⁱ	59.2 (4)
C5—C6—N3—Zn1	−9.4 (6)	N2—N3—Zn1—N6	−23.7 (3)
C11—C12—N4—N5	−178.7 (4)	C6—N3—Zn1—N6	166.9 (3)
C7—C12—N4—N5	0.5 (4)	N2—N3—Zn1—N9	95.9 (3)
C12—N4—N5—N6	−0.3 (4)	C6—N3—Zn1—N9	−73.5 (3)
N4—N5—N6—C7	0.0 (4)	N2—N3—Zn1—N1ⁱⁱ	−143.0 (2)
N4—N5—N6—Zn1	−178.4 (2)	C6—N3—Zn1—N1ⁱⁱ	47.6 (3)
C12—C7—N6—N5	0.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H27···N7	0.90	1.96	2.824 (4)	160
N10—H27···N8	0.90	2.42	3.052 (4)	127
N10—H26···N4ⁱⁱⁱ	0.90	1.93	2.821 (4)	171

Symmetry code: (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	(C₆H₁₆N)[Zn(C₆H₄N₃)₃]
M_r	521.93
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.9439 (15), 9.8058 (13), 21.585 (3)
β (°)	104.212 (2)
V (Å³)	2450.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.35 × 0.2 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.286, 0.322
No. of measured, independent and observed [I > 2σ(I)] reflections	11639, 4107, 2645
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.095, 0.96
No. of reflections	4107
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.54

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—Zn1ⁱ	2.000 (3)	N6—Zn1	1.982 (3)
N3—Zn1	1.990 (3)	Zn1—N1ⁱⁱ	2.000 (3)

N6—Zn1—N1ⁱⁱ	106.15 (12)	N3—Zn1—N1ⁱⁱ	113.61 (12)
N9—Zn1—N1ⁱⁱ	111.79 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H27···N7	0.90	1.96	2.824 (4)	159.7
N10—H27···N8	0.90	2.42	3.052 (4)	127.0
N10—H26···N4ⁱⁱⁱ	0.90	1.93	2.821 (4)	171.2

Symmetry code: (iii) x, −y+1/2, z+1/2.

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shao, K. Z., Zhao, Y. H., Xing, Y., Lan, Y. Q., Wang, X. L., Su, Z. M. & Wang, R. S. (2008). Cryst. Growth Des. 8, 2986–2989. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yaghi, O. M., Li, H., David, C., Richardson, D. & Groy, T. L. (1998). Acc. Chem. Res. 31, 474–484. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page m884

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