catena-Poly[[(2,2′-diquinolyl-κ²N,N′)zinc(II)]-μ-isophthalato-κ²O:O′]

In the title complex, [Zn(C₈H₄O₄)(C₁₈H₁₂N₂)]_n, isophthalate (ipa) acts as a bis-monodentate ligand, forming a one-dimensional helical chain. A significant π–π stacking inter­action helps to pack adjacent chains into a mol­ecular zipper. The Zn atom is coordinated by two N and two O atoms in a distorted tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.03
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: TEXSAN (Molecular Structure Corporation, 1999); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXL97.

Poly[µ-isophthalato-O,O-[(2,2'-diquinolyl-N,N')zinc(II)]]

Crystal data

[Zn(C18H12N2)(C8H4O4)]	F(000) = 992
Mr = 485.78	Dx = 1.528 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P2ybc	Cell parameters from 15151 reflections
a = 8.664 (4) Å	θ = 12–18°
b = 11.779 (3) Å	µ = 1.20 mm^−1
c = 20.803 (7) Å	T = 173 K
β = 95.812 (16)°	Cuboid, colourless
V = 2112.1 (13) Å^3	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection

Rigaku Weissenberg IP diffractometer	4835 independent reflections
Radiation source: rotor target	3719 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
scintillation counter scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: ψ scans (teXsan; Molecular Structure Corporation, 1999)	h = −11→11
Tmin = 0.831, Tmax = 0.864	k = −15→15
20895 measured reflections	l = −27→25

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 0.6028P] where P = (Fo^2 + 2Fc^2)/3
4835 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. IR (KBr, cm^-1): 3433 s, 2927w, 1617 s, 1560w, 1510w, 1435w, 1384 s, 1145w, 1105w, 826m, 783m, 749m.

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	0.06384 (3)	0.66064 (2)	0.390722 (11)	0.04143 (10)
O1	−0.0663 (2)	0.56322 (14)	0.33283 (8)	0.0570 (4)
O2	−0.2251 (3)	0.70940 (17)	0.32667 (10)	0.0757 (6)
O3	−0.1436 (3)	0.27381 (17)	0.16342 (9)	0.0730 (6)
O4	−0.3681 (3)	0.2509 (2)	0.10830 (13)	0.0975 (8)
N1	0.0266 (2)	0.72153 (15)	0.48144 (9)	0.0427 (4)
N2	0.1909 (2)	0.54167 (15)	0.44756 (8)	0.0413 (4)
C1	−0.0626 (3)	0.81243 (19)	0.49582 (12)	0.0483 (5)
C2	−0.1511 (3)	0.8711 (2)	0.44665 (14)	0.0627 (7)
H2	−0.1495	0.8480	0.4030	0.075*
C3	−0.2399 (4)	0.9617 (2)	0.46131 (17)	0.0768 (9)
H3	−0.2992	1.0011	0.4274	0.092*
C4	−0.2450 (4)	0.9973 (3)	0.52477 (17)	0.0794 (9)
H4	−0.3085	1.0598	0.5340	0.095*
C5	−0.1599 (4)	0.9432 (3)	0.57310 (17)	0.0773 (9)
H5	−0.1623	0.9689	0.6163	0.093*
C6	−0.0668 (4)	0.8486 (2)	0.56059 (13)	0.0594 (7)
C7	0.0225 (5)	0.7882 (3)	0.60869 (13)	0.0749 (9)
H7	0.0219	0.8104	0.6526	0.090*
C8	0.1098 (4)	0.6985 (2)	0.59393 (12)	0.0657 (8)
H8	0.1702	0.6579	0.6270	0.079*
C9	0.1098 (3)	0.66624 (18)	0.52895 (10)	0.0445 (5)
C10	0.2005 (3)	0.56659 (18)	0.51020 (10)	0.0421 (5)
C11	0.2911 (3)	0.5020 (2)	0.55634 (11)	0.0520 (6)
H11	0.2991	0.5234	0.6006	0.062*
C12	0.3673 (3)	0.4087 (2)	0.53782 (12)	0.0553 (6)
H12	0.4266	0.3637	0.5692	0.066*
C13	0.3583 (3)	0.3791 (2)	0.47231 (12)	0.0491 (5)
C14	0.4359 (3)	0.2845 (2)	0.44920 (15)	0.0634 (7)
H14	0.4962	0.2369	0.4788	0.076*
C15	0.4253 (4)	0.2612 (2)	0.38559 (17)	0.0741 (8)
H15	0.4783	0.1972	0.3708	0.089*
C16	0.3370 (4)	0.3302 (2)	0.34095 (15)	0.0730 (9)
H16	0.3311	0.3126	0.2962	0.088*
C17	0.2593 (4)	0.4227 (2)	0.36108 (13)	0.0613 (7)
H17	0.1992	0.4686	0.3305	0.074*
C18	0.2688 (3)	0.44943 (18)	0.42762 (11)	0.0453 (5)
C19	−0.2854 (3)	0.29597 (19)	0.15189 (11)	0.0473 (5)
C21	−0.1915 (3)	0.6132 (2)	0.31126 (10)	0.0483 (5)
C22	−0.3006 (3)	0.54437 (18)	0.26651 (10)	0.0422 (5)
C23	−0.2464 (3)	0.45165 (17)	0.23413 (10)	0.0406 (5)
H23	−0.1400	0.4310	0.2412	0.049*
C24	−0.3464 (3)	0.38908 (18)	0.19150 (10)	0.0413 (5)
C25	−0.5025 (3)	0.4159 (2)	0.18412 (12)	0.0535 (6)
H25	−0.5725	0.3718	0.1562	0.064*
C26	−0.5571 (3)	0.5069 (2)	0.21727 (13)	0.0592 (6)
H26	−0.6646	0.5247	0.2123	0.071*
C27	−0.4563 (3)	0.5719 (2)	0.25744 (12)	0.0524 (6)
H27	−0.4940	0.6358	0.2789	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.04700 (17)	0.03960 (14)	0.03648 (14)	−0.00018 (11)	−0.00163 (10)	0.00182 (10)
O1	0.0615 (12)	0.0538 (9)	0.0518 (9)	−0.0054 (8)	−0.0131 (8)	−0.0018 (8)
O2	0.0800 (15)	0.0603 (11)	0.0852 (14)	0.0009 (10)	0.0004 (11)	−0.0313 (11)
O3	0.0668 (14)	0.0801 (13)	0.0685 (12)	0.0215 (11)	−0.0111 (10)	−0.0337 (10)
O4	0.0708 (15)	0.1025 (17)	0.1171 (19)	−0.0126 (13)	−0.0011 (14)	−0.0679 (15)
N1	0.0428 (11)	0.0413 (9)	0.0436 (9)	−0.0049 (8)	0.0016 (8)	−0.0036 (8)
N2	0.0417 (11)	0.0423 (9)	0.0395 (9)	0.0007 (8)	0.0014 (8)	0.0048 (8)
C1	0.0480 (14)	0.0413 (11)	0.0553 (13)	−0.0065 (10)	0.0040 (11)	−0.0110 (10)
C2	0.0683 (19)	0.0528 (13)	0.0639 (16)	0.0104 (13)	−0.0081 (14)	−0.0162 (12)
C3	0.079 (2)	0.0585 (16)	0.089 (2)	0.0145 (15)	−0.0125 (17)	−0.0163 (16)
C4	0.081 (2)	0.0581 (16)	0.098 (2)	0.0077 (15)	0.0063 (19)	−0.0292 (17)
C5	0.093 (3)	0.0636 (17)	0.077 (2)	0.0028 (16)	0.0181 (18)	−0.0264 (16)
C6	0.0701 (19)	0.0531 (14)	0.0560 (14)	−0.0060 (13)	0.0114 (13)	−0.0145 (12)
C7	0.109 (3)	0.0700 (18)	0.0462 (14)	0.0022 (18)	0.0090 (15)	−0.0141 (14)
C8	0.092 (2)	0.0631 (15)	0.0417 (12)	0.0020 (15)	0.0030 (13)	−0.0021 (12)
C9	0.0484 (14)	0.0447 (11)	0.0405 (11)	−0.0087 (10)	0.0044 (9)	−0.0004 (9)
C10	0.0396 (12)	0.0460 (11)	0.0402 (11)	−0.0094 (9)	0.0016 (9)	0.0075 (9)
C11	0.0522 (15)	0.0608 (14)	0.0418 (11)	−0.0057 (11)	−0.0008 (10)	0.0111 (11)
C12	0.0466 (14)	0.0585 (14)	0.0587 (14)	−0.0008 (11)	−0.0042 (11)	0.0206 (12)
C13	0.0421 (13)	0.0458 (12)	0.0592 (14)	−0.0015 (10)	0.0049 (11)	0.0156 (11)
C14	0.0546 (17)	0.0528 (14)	0.0829 (19)	0.0115 (12)	0.0077 (14)	0.0147 (14)
C15	0.078 (2)	0.0554 (15)	0.092 (2)	0.0192 (15)	0.0250 (17)	0.0045 (15)
C16	0.092 (2)	0.0647 (17)	0.0651 (17)	0.0194 (16)	0.0223 (16)	0.0003 (14)
C17	0.0743 (19)	0.0585 (15)	0.0519 (14)	0.0170 (13)	0.0104 (13)	0.0048 (12)
C18	0.0446 (13)	0.0429 (11)	0.0488 (12)	0.0015 (9)	0.0072 (10)	0.0083 (10)
C19	0.0560 (16)	0.0415 (11)	0.0446 (12)	−0.0062 (10)	0.0062 (11)	0.0002 (10)
C21	0.0585 (16)	0.0494 (12)	0.0370 (11)	−0.0070 (11)	0.0046 (10)	−0.0032 (10)
C22	0.0486 (14)	0.0425 (11)	0.0351 (10)	−0.0010 (9)	0.0033 (9)	0.0024 (9)
C23	0.0429 (13)	0.0421 (11)	0.0359 (10)	0.0010 (9)	0.0001 (9)	0.0022 (9)
C24	0.0457 (13)	0.0392 (10)	0.0389 (10)	−0.0042 (9)	0.0031 (9)	0.0017 (9)
C25	0.0464 (14)	0.0565 (14)	0.0557 (13)	−0.0079 (11)	−0.0033 (11)	−0.0007 (12)
C26	0.0410 (14)	0.0690 (16)	0.0671 (16)	0.0061 (12)	0.0028 (12)	−0.0004 (13)
C27	0.0525 (15)	0.0510 (13)	0.0544 (13)	0.0078 (11)	0.0082 (11)	−0.0025 (11)

Geometric parameters (Å, º)

Zn1—O3^i	1.9183 (18)	C9—C10	1.486 (3)
Zn1—O1	1.9401 (17)	C10—C11	1.402 (3)
Zn1—N1	2.0746 (19)	C11—C12	1.358 (4)
Zn1—N2	2.0763 (18)	C11—H11	0.9500
O1—C21	1.275 (3)	C12—C13	1.401 (4)
O2—C21	1.221 (3)	C12—H12	0.9500
O3—C19	1.255 (3)	C13—C14	1.410 (4)
O3—Zn1^ii	1.9183 (18)	C13—C18	1.416 (3)
O4—C19	1.219 (3)	C14—C15	1.346 (4)
N1—C9	1.333 (3)	C14—H14	0.9500
N1—C1	1.371 (3)	C15—C16	1.402 (4)
N2—C10	1.330 (3)	C15—H15	0.9500
N2—C18	1.365 (3)	C16—C17	1.368 (4)
C1—C2	1.397 (4)	C16—H16	0.9500
C1—C6	1.417 (3)	C17—C18	1.414 (3)
C2—C3	1.368 (4)	C17—H17	0.9500
C2—H2	0.9500	C19—C24	1.500 (3)
C3—C4	1.390 (4)	C21—C22	1.496 (3)
C3—H3	0.9500	C22—C27	1.382 (3)
C4—C5	1.346 (4)	C22—C23	1.390 (3)
C4—H4	0.9500	C23—C24	1.387 (3)
C5—C6	1.415 (4)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.383 (3)
C6—C7	1.396 (4)	C25—C26	1.384 (4)
C7—C8	1.353 (4)	C25—H25	0.9500
C7—H7	0.9500	C26—C27	1.378 (4)
C8—C9	1.404 (3)	C26—H26	0.9500
C8—H8	0.9500	C27—H27	0.9500
O3^i—Zn1—O1	105.53 (8)	C10—C11—H11	120.0
O3^i—Zn1—N1	113.10 (9)	C11—C12—C13	119.8 (2)
O1—Zn1—N1	129.42 (8)	C11—C12—H12	120.1
O3^i—Zn1—N2	126.98 (9)	C13—C12—H12	120.1
O1—Zn1—N2	101.29 (8)	C12—C13—C14	123.1 (2)
N1—Zn1—N2	80.66 (8)	C12—C13—C18	117.8 (2)
C21—O1—Zn1	111.45 (15)	C14—C13—C18	119.1 (2)
C19—O3—Zn1^ii	115.85 (16)	C15—C14—C13	120.6 (3)
C9—N1—C1	119.63 (19)	C15—C14—H14	119.7
C9—N1—Zn1	112.53 (15)	C13—C14—H14	119.7
C1—N1—Zn1	127.70 (16)	C14—C15—C16	120.7 (3)
C10—N2—C18	119.32 (19)	C14—C15—H15	119.6
C10—N2—Zn1	112.69 (15)	C16—C15—H15	119.6
C18—N2—Zn1	127.87 (15)	C17—C16—C15	120.8 (3)
N1—C1—C2	120.4 (2)	C17—C16—H16	119.6
N1—C1—C6	120.8 (2)	C15—C16—H16	119.6
C2—C1—C6	118.9 (2)	C16—C17—C18	119.7 (3)
C3—C2—C1	120.1 (3)	C16—C17—H17	120.2
C3—C2—H2	119.9	C18—C17—H17	120.2
C1—C2—H2	119.9	N2—C18—C17	119.6 (2)
C2—C3—C4	121.3 (3)	N2—C18—C13	121.4 (2)
C2—C3—H3	119.3	C17—C18—C13	119.1 (2)
C4—C3—H3	119.3	O4—C19—O3	122.8 (2)
C5—C4—C3	119.9 (3)	O4—C19—C24	120.9 (2)
C5—C4—H4	120.0	O3—C19—C24	116.1 (2)
C3—C4—H4	120.0	O2—C21—O1	123.6 (2)
C4—C5—C6	121.0 (3)	O2—C21—C22	120.9 (2)
C4—C5—H5	119.5	O1—C21—C22	115.5 (2)
C6—C5—H5	119.5	C27—C22—C23	119.4 (2)
C7—C6—C5	123.7 (3)	C27—C22—C21	120.3 (2)
C7—C6—C1	117.6 (2)	C23—C22—C21	120.3 (2)
C5—C6—C1	118.8 (3)	C24—C23—C22	120.5 (2)
C8—C7—C6	121.2 (2)	C24—C23—H23	119.7
C8—C7—H7	119.4	C22—C23—H23	119.7
C6—C7—H7	119.4	C25—C24—C23	119.4 (2)
C7—C8—C9	119.0 (3)	C25—C24—C19	120.1 (2)
C7—C8—H8	120.5	C23—C24—C19	120.5 (2)
C9—C8—H8	120.5	C24—C25—C26	120.1 (2)
N1—C9—C8	121.9 (2)	C24—C25—H25	119.9
N1—C9—C10	116.87 (19)	C26—C25—H25	119.9
C8—C9—C10	121.2 (2)	C27—C26—C25	120.4 (2)
N2—C10—C11	121.7 (2)	C27—C26—H26	119.8
N2—C10—C9	116.70 (19)	C25—C26—H26	119.8
C11—C10—C9	121.6 (2)	C26—C27—C22	120.1 (2)
C12—C11—C10	120.0 (2)	C26—C27—H27	119.9
C12—C11—H11	120.0	C22—C27—H27	119.9

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