A linear trinuclear CaZn2 complex with bridging benzoate ligands

Necefoglu, H.; Clegg, W.; Scott, A.J.

doi:10.1107/S160053680200209X

A linear trinuclear CaZn₂ complex with bridging benzoate ligands

The title complex, [CaZn₂(C₇H₅O₂)₆(C₁₀H₁₄N₂O)₂], has a centrosymmetric molecule containing a linear array of two zinc and one central calcium ions bridged by two sets of three unsymmetrical benzoate ligands. Zinc is additionally coordinated by a nitrogen-base ligand to give distorted tetrahedral geometry, while the coordination of calcium by six benzoate O atoms is close to regular octahedral.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200209X/na6136sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680200209X/na6136Isup2.hkl Contains datablock I

CCDC reference: 182589

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.005 Å
R factor = 0.040
wR factor = 0.097
Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.50
         From the CIF: _reflns_number_total               4938
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5522
         Completeness (_total/calc)             89.42%
          Alert B: < 90% complete (theta max?)

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.927
          Tmax scaled      0.857 Tmin scaled      0.797


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

The title compound, (I), was obtained as a minor product in the preparation of the bridged dimeric complex [Zn₂(benzoate)₄(DENA)₂], where DENA is N,N'-diethylnicotinamide. The calcium is derived from impurities in the reagents. Crystals of (I) were separated manually from those of the major product, which has also been crystallographically characterized (Necefoglu et al., 2002).

The molecule (Fig. 1) has crystallographic inversion symmetry. Six benzoate bridges link the central calcium ion with the two zinc ions, the three metal ions forming a symmetrical linear array. Each zinc ion is additionally coordinated by a monodentate DENA ligand to give somewhat distorted tetrahedral coordination by one N and three O atoms. Coordination of calcium is reasonably close to ideal octahedral (Table 1). There are no significant intermolecular interactions.

The benzoate ligands are not symmetrical. Each has one short C—O bond, which coordinates to Ca, and one longer C—O bond, coordinated to Zn; there is thus some localization of double and single bonds in the carboxylate groups. The Ca—O—C angles are considerably greater than Zn—O—C. These features are similar to those of a previously reported CaZn₂ complex with crotonate bridging ligands, which has been compared in detail with other MZn₂ analogous complexes having a range of transition and main-group metals M (Clegg et al., 1988).

Experimental top

The title complex was obtained as a minor product in the synthesis of a dimeric zinc complex with benzoate bridges (Necefolglu, 2002). The two products could be distinguished by their different crystal habits. The minor product has its origin in the presence of calcium ions in the unpurified tap water used in the synthesis.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: local programs; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top

Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.

(I) top

Crystal data top

[CaZn₂(C₇H₅O₂)₆(C₁₀H₁₄N₂O)₂]	F(000) = 1300
M_r = 1253.94	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.347 (2) Å	Cell parameters from 7387 reflections
b = 10.7691 (13) Å	θ = 2.0–25.4°
c = 17.647 (2) Å	µ = 0.96 mm⁻¹
β = 107.207 (3)°	T = 160 K
V = 2967.6 (6) Å³	Block, colourless
Z = 2	0.30 × 0.20 × 0.16 mm

Data collection top

Siemens SMART 1K CCD diffractometer	4938 independent reflections
Radiation source: sealed tube	4193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.5°, θ_min = 1.5°
ω rotation with narrow frames scans	h = −17→18
Absorption correction: multi-scan (SHELXTL; Sheldrick, 1997)	k = −12→12
T_min = 0.860, T_max = 0.925	l = −20→15
12317 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0348P)² + 2.7427P] where P = (F_o² + 2F_c²)/3
4938 reflections	(Δ/σ)_max < 0.001
376 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[CaZn₂(C₇H₅O₂)₆(C₁₀H₁₄N₂O)₂]	V = 2967.6 (6) Å³
M_r = 1253.94	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.347 (2) Å	µ = 0.96 mm⁻¹
b = 10.7691 (13) Å	T = 160 K
c = 17.647 (2) Å	0.30 × 0.20 × 0.16 mm
β = 107.207 (3)°

Data collection top

Siemens SMART 1K CCD diffractometer	4938 independent reflections
Absorption correction: multi-scan (SHELXTL; Sheldrick, 1997)	4193 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.925	R_int = 0.039
12317 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.12	Δρ_max = 0.41 e Å⁻³
4938 reflections	Δρ_min = −0.48 e Å⁻³
376 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn	0.20197 (2)	0.19710 (3)	0.04078 (2)	0.02835 (11)
Ca	0.0000	0.0000	0.0000	0.02526 (19)
N1	0.31448 (15)	0.2969 (2)	0.05654 (15)	0.0326 (6)
C1	0.3254 (2)	0.4128 (3)	0.0858 (2)	0.0402 (8)
H1	0.2846	0.4472	0.1087	0.048*
C2	0.4010 (2)	0.4774 (3)	0.0961 (2)	0.0494 (9)
H2	0.4008	0.5642	0.1054	0.059*
C3	0.4671 (2)	0.4218 (3)	0.0753 (2)	0.0457 (9)
H3	0.5205	0.4637	0.0862	0.055*
C4	0.45723 (18)	0.3021 (3)	0.04543 (18)	0.0331 (7)
C5	0.37961 (18)	0.2441 (3)	0.03646 (18)	0.0326 (7)
H5	0.3727	0.1613	0.0171	0.039*
C6	0.52377 (18)	0.2415 (3)	0.01435 (18)	0.0329 (7)
O1	0.52052 (14)	0.2591 (2)	−0.05501 (13)	0.0457 (6)
N2	0.58412 (15)	0.1708 (2)	0.06381 (15)	0.0336 (6)
C7	0.64967 (18)	0.1126 (3)	0.03345 (19)	0.0368 (7)
H7A	0.6241	0.0942	−0.0237	0.044*
H7B	0.6681	0.0330	0.0613	0.044*
C8	0.72458 (19)	0.1991 (3)	0.0403 (2)	0.0421 (8)
H8A	0.7680	0.1551	0.0224	0.063*
H8B	0.7484	0.2208	0.0965	0.063*
H8C	0.7075	0.2750	0.0090	0.063*
C9	0.5898 (2)	0.1471 (3)	0.14682 (18)	0.0415 (8)
H9A	0.5614	0.2180	0.1645	0.050*
H9B	0.6505	0.1459	0.1796	0.050*
C10	0.5496 (2)	0.0237 (4)	0.1576 (2)	0.0596 (11)
H10A	0.4962	0.0128	0.1146	0.089*
H10B	0.5370	0.0271	0.2085	0.089*
H10C	0.5880	−0.0464	0.1579	0.089*
O2	0.13990 (12)	0.32848 (19)	0.07535 (12)	0.0331 (5)
O3	0.02892 (14)	0.2024 (2)	0.03401 (14)	0.0445 (6)
C11	0.06069 (19)	0.3030 (3)	0.06260 (17)	0.0305 (7)
C12	0.00513 (17)	0.3999 (3)	0.08220 (16)	0.0285 (6)
C13	0.0394 (2)	0.5109 (3)	0.11757 (19)	0.0364 (7)
H13	0.0994	0.5250	0.1315	0.044*
C14	−0.0128 (2)	0.5995 (3)	0.1358 (2)	0.0462 (8)
H14	0.0083	0.6770	0.1593	0.055*
C15	−0.1001 (2)	0.5788 (3)	0.1178 (2)	0.0454 (9)
H15	−0.1370	0.6380	0.1307	0.054*
C16	−0.1344 (2)	0.4694 (3)	0.0823 (2)	0.0429 (8)
H16	−0.1947	0.4582	0.0672	0.051*
C17	−0.08257 (19)	0.3798 (3)	0.06443 (18)	0.0371 (7)
H17	−0.1057	0.3010	0.0450	0.044*
O4	0.18972 (12)	0.14893 (19)	−0.06907 (12)	0.0352 (5)
O5	0.07706 (14)	0.0230 (2)	−0.09016 (13)	0.0449 (6)
C18	0.13757 (18)	0.0683 (3)	−0.10940 (17)	0.0306 (7)
C19	0.15360 (17)	0.0265 (3)	−0.18477 (17)	0.0292 (6)
C20	0.11088 (19)	−0.0769 (3)	−0.22417 (19)	0.0399 (8)
H20	0.0714	−0.1190	−0.2031	0.048*
C21	0.1268 (2)	−0.1202 (3)	−0.2926 (2)	0.0473 (9)
H21	0.0957	−0.1897	−0.3197	0.057*
C22	0.1856 (2)	−0.0579 (4)	−0.3216 (2)	0.0487 (9)
H22	0.2004	−0.0875	−0.3665	0.058*
C23	0.2278 (2)	0.0450 (3)	−0.28328 (19)	0.0453 (8)
H23	0.2673	0.0891	−0.3034	0.054*
C24	0.21239 (19)	0.0873 (3)	−0.21453 (18)	0.0369 (7)
H24	0.2407	0.1601	−0.1895	0.044*
O6	0.25188 (13)	0.0520 (2)	0.10273 (12)	0.0367 (5)
O7	0.12999 (13)	−0.0504 (2)	0.09010 (13)	0.0442 (6)
C25	0.20928 (18)	−0.0414 (3)	0.11458 (17)	0.0319 (7)
C26	0.26071 (18)	−0.1454 (3)	0.16197 (16)	0.0309 (7)
C27	0.2201 (2)	−0.2521 (3)	0.17617 (19)	0.0435 (8)
H27	0.1595	−0.2584	0.1561	0.052*
C28	0.2677 (2)	−0.3484 (3)	0.2199 (2)	0.0521 (9)
H28	0.2403	−0.4241	0.2259	0.063*
C29	0.3555 (2)	−0.3397 (3)	0.24893 (19)	0.0463 (9)
H29	0.3871	−0.4007	0.2846	0.056*
C30	0.3963 (2)	−0.2341 (3)	0.23457 (19)	0.0419 (8)
H30	0.4571	−0.2315	0.2496	0.050*
C31	0.34922 (18)	−0.1373 (3)	0.19134 (17)	0.0340 (7)
H31	0.3776	−0.0633	0.1838	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.02146 (18)	0.02655 (19)	0.0385 (2)	−0.00234 (14)	0.01103 (14)	−0.00277 (15)
Ca	0.0171 (4)	0.0261 (4)	0.0337 (4)	−0.0032 (3)	0.0093 (3)	−0.0029 (3)
N1	0.0243 (12)	0.0295 (14)	0.0447 (15)	−0.0023 (11)	0.0111 (11)	−0.0059 (11)
C1	0.0341 (17)	0.0354 (18)	0.057 (2)	−0.0060 (14)	0.0237 (15)	−0.0112 (16)
C2	0.0422 (19)	0.036 (2)	0.077 (3)	−0.0135 (16)	0.0285 (18)	−0.0182 (18)
C3	0.0315 (17)	0.045 (2)	0.064 (2)	−0.0150 (15)	0.0195 (16)	−0.0185 (17)
C4	0.0253 (15)	0.0350 (17)	0.0377 (17)	−0.0031 (13)	0.0071 (13)	−0.0023 (14)
C5	0.0279 (15)	0.0276 (16)	0.0431 (18)	0.0001 (13)	0.0117 (13)	−0.0038 (14)
C6	0.0249 (15)	0.0328 (17)	0.0403 (18)	−0.0048 (13)	0.0088 (14)	−0.0050 (14)
O1	0.0388 (13)	0.0568 (16)	0.0432 (14)	0.0108 (11)	0.0147 (11)	0.0046 (11)
N2	0.0275 (13)	0.0364 (15)	0.0370 (14)	0.0006 (11)	0.0097 (11)	−0.0024 (12)
C7	0.0283 (16)	0.0382 (19)	0.0432 (18)	0.0051 (14)	0.0098 (14)	−0.0066 (15)
C8	0.0278 (16)	0.046 (2)	0.054 (2)	0.0000 (15)	0.0147 (15)	−0.0032 (16)
C9	0.0349 (17)	0.052 (2)	0.0353 (17)	0.0007 (16)	0.0062 (14)	−0.0033 (16)
C10	0.053 (2)	0.077 (3)	0.045 (2)	−0.020 (2)	0.0097 (18)	0.006 (2)
O2	0.0273 (11)	0.0330 (12)	0.0402 (12)	−0.0004 (9)	0.0122 (9)	−0.0036 (9)
O3	0.0447 (13)	0.0304 (13)	0.0613 (15)	−0.0049 (11)	0.0199 (11)	−0.0100 (11)
C11	0.0327 (16)	0.0280 (17)	0.0329 (16)	−0.0021 (13)	0.0129 (13)	0.0006 (13)
C12	0.0281 (15)	0.0284 (16)	0.0316 (15)	0.0018 (13)	0.0130 (12)	0.0039 (13)
C13	0.0316 (16)	0.0325 (17)	0.0487 (19)	−0.0025 (14)	0.0174 (14)	−0.0032 (15)
C14	0.052 (2)	0.0306 (18)	0.063 (2)	0.0003 (16)	0.0291 (18)	−0.0047 (17)
C15	0.050 (2)	0.038 (2)	0.059 (2)	0.0131 (16)	0.0325 (18)	0.0108 (17)
C16	0.0306 (17)	0.050 (2)	0.052 (2)	0.0053 (16)	0.0186 (15)	0.0083 (17)
C17	0.0304 (16)	0.0379 (19)	0.0449 (18)	−0.0047 (14)	0.0142 (14)	0.0001 (15)
O4	0.0333 (11)	0.0318 (12)	0.0418 (12)	−0.0026 (10)	0.0132 (10)	−0.0040 (10)
O5	0.0376 (12)	0.0562 (15)	0.0486 (14)	−0.0097 (11)	0.0245 (11)	−0.0083 (12)
C18	0.0253 (15)	0.0306 (17)	0.0371 (17)	0.0023 (13)	0.0110 (13)	0.0012 (13)
C19	0.0226 (14)	0.0313 (17)	0.0320 (16)	0.0019 (12)	0.0055 (12)	0.0000 (13)
C20	0.0286 (16)	0.047 (2)	0.0427 (18)	−0.0037 (15)	0.0091 (14)	−0.0061 (16)
C21	0.0410 (19)	0.051 (2)	0.0421 (19)	0.0030 (17)	0.0001 (16)	−0.0146 (17)
C22	0.046 (2)	0.066 (3)	0.0339 (18)	0.0181 (19)	0.0103 (15)	−0.0015 (17)
C23	0.0437 (19)	0.058 (2)	0.0395 (18)	0.0077 (17)	0.0212 (16)	0.0072 (17)
C24	0.0358 (17)	0.0373 (18)	0.0406 (18)	0.0014 (14)	0.0160 (14)	0.0032 (15)
O6	0.0315 (11)	0.0323 (12)	0.0452 (13)	0.0007 (10)	0.0097 (10)	0.0053 (10)
O7	0.0243 (11)	0.0497 (15)	0.0519 (14)	0.0000 (10)	0.0007 (10)	0.0043 (11)
C25	0.0294 (16)	0.0376 (18)	0.0283 (15)	0.0005 (14)	0.0077 (13)	−0.0051 (13)
C26	0.0312 (15)	0.0338 (17)	0.0259 (15)	−0.0014 (13)	0.0057 (12)	−0.0033 (13)
C27	0.0372 (18)	0.046 (2)	0.0435 (19)	−0.0085 (16)	0.0062 (15)	0.0065 (16)
C28	0.060 (2)	0.043 (2)	0.047 (2)	−0.0087 (18)	0.0058 (18)	0.0133 (17)
C29	0.058 (2)	0.043 (2)	0.0325 (18)	0.0128 (18)	0.0050 (16)	0.0059 (15)
C30	0.0329 (17)	0.049 (2)	0.0415 (18)	0.0106 (16)	0.0083 (15)	−0.0015 (16)
C31	0.0290 (16)	0.0360 (18)	0.0357 (17)	0.0020 (14)	0.0073 (13)	−0.0001 (14)

Geometric parameters (Å, º) top

Zn—N1	2.077 (2)	C23—C24	1.387 (4)
Zn—O2	1.942 (2)	O6—C25	1.275 (4)
Zn—O4	1.959 (2)	O7—C25	1.243 (3)
Zn—O6	1.943 (2)	C25—C26	1.498 (4)
Ca—O3	2.273 (2)	C26—C27	1.387 (4)
Ca—O3ⁱ	2.273 (2)	C26—C31	1.388 (4)
Ca—O5	2.316 (2)	C27—C28	1.386 (5)
Ca—O5ⁱ	2.316 (2)	C28—C29	1.378 (5)
Ca—O7	2.311 (2)	C29—C30	1.379 (5)
Ca—O7ⁱ	2.311 (2)	C30—C31	1.384 (4)
N1—C1	1.342 (4)	C1—H1	0.950
N1—C5	1.343 (4)	C2—H2	0.950
C1—C2	1.382 (4)	C3—H3	0.950
C2—C3	1.377 (5)	C5—H5	0.950
C3—C4	1.384 (4)	C7—H7A	0.990
C4—C5	1.380 (4)	C7—H7B	0.990
C4—C6	1.505 (4)	C8—H8A	0.980
C6—O1	1.224 (4)	C8—H8B	0.980
C6—N2	1.344 (4)	C8—H8C	0.980
N2—C7	1.472 (4)	C9—H9A	0.990
N2—C9	1.463 (4)	C9—H9B	0.990
C7—C8	1.515 (4)	C10—H10A	0.980
C9—C10	1.519 (5)	C10—H10B	0.980
O2—C11	1.277 (3)	C10—H10C	0.980
O3—C11	1.242 (3)	C13—H13	0.950
C11—C12	1.489 (4)	C14—H14	0.950
C12—C13	1.388 (4)	C15—H15	0.950
C12—C17	1.391 (4)	C16—H16	0.950
C13—C14	1.380 (4)	C17—H17	0.950
C14—C15	1.386 (5)	C20—H20	0.950
C15—C16	1.374 (5)	C21—H21	0.950
C16—C17	1.381 (4)	C22—H22	0.950
O4—C18	1.276 (3)	C23—H23	0.950
O5—C18	1.238 (3)	C24—H24	0.950
C18—C19	1.499 (4)	C27—H27	0.950
C19—C20	1.387 (4)	C28—H28	0.950
C19—C24	1.388 (4)	C29—H29	0.950
C20—C21	1.390 (4)	C30—H30	0.950
C21—C22	1.388 (5)	C31—H31	0.950
C22—C23	1.373 (5)

N1—Zn—O2	96.04 (9)	O7—C25—C26	119.4 (3)
N1—Zn—O4	95.55 (9)	C25—C26—C27	120.1 (3)
N1—Zn—O6	97.64 (9)	C25—C26—C31	120.8 (3)
O2—Zn—O4	126.44 (9)	C27—C26—C31	119.1 (3)
O2—Zn—O6	125.51 (9)	C26—C27—C28	120.1 (3)
O4—Zn—O6	104.28 (9)	C27—C28—C29	120.5 (3)
O3—Ca—O3ⁱ	180.00 (12)	C28—C29—C30	119.7 (3)
O3—Ca—O5	88.06 (8)	C29—C30—C31	120.2 (3)
O3ⁱ—Ca—O5ⁱ	88.06 (8)	C26—C31—C30	120.4 (3)
O3—Ca—O5ⁱ	91.94 (8)	N1—C1—H1	119.7
O3ⁱ—Ca—O5	91.94 (8)	C2—C1—H1	117.4
O3—Ca—O7	88.09 (8)	C3—C2—H2	121.1
O3ⁱ—Ca—O7ⁱ	88.09 (8)	C1—C2—H2	118.0
O3—Ca—O7ⁱ	91.91 (8)	C2—C3—H3	119.1
O3ⁱ—Ca—O7	91.91 (8)	C4—C3—H3	121.1
O5—Ca—O5ⁱ	180.00 (7)	N1—C5—H5	118.2
O5—Ca—O7	85.49 (8)	C4—C5—H5	118.2
O5ⁱ—Ca—O7ⁱ	85.49 (8)	N2—C7—H7A	108.8
O5ⁱ—Ca—O7	94.51 (8)	C8—C7—H7A	107.0
O5—Ca—O7ⁱ	94.51 (8)	N2—C7—H7B	109.5
O7—Ca—O7ⁱ	180.00 (18)	C8—C7—H7B	111.9
Zn—N1—C1	123.0 (2)	H7A—C7—H7B	107.9
Zn—N1—C5	119.0 (2)	C7—C8—H8A	108.8
C1—N1—C5	118.0 (3)	C7—C8—H8B	107.3
N1—C1—C2	122.0 (3)	H8A—C8—H8B	109.5
C1—C2—C3	119.2 (3)	C7—C8—H8C	112.3
C2—C3—C4	119.6 (3)	H8A—C8—H8C	109.5
C3—C4—C5	117.7 (3)	H8B—C8—H8C	109.5
C3—C4—C6	121.8 (3)	N2—C9—H9A	106.6
C5—C4—C6	120.1 (3)	C10—C9—H9A	112.0
N1—C5—C4	123.5 (3)	N2—C9—H9B	110.0
C4—C6—O1	118.3 (3)	C10—C9—H9B	108.1
C4—C6—N2	118.7 (3)	H9A—C9—H9B	107.9
O1—C6—N2	123.0 (3)	C9—C10—H10A	109.0
C6—N2—C7	118.6 (3)	C9—C10—H10B	107.3
C6—N2—C9	124.5 (3)	H10A—C10—H10B	109.5
C7—N2—C9	117.0 (2)	C9—C10—H10C	112.0
N2—C7—C8	111.6 (3)	H10A—C10—H10C	109.5
N2—C9—C10	112.1 (3)	H10B—C10—H10C	109.5
Zn—O2—C11	112.66 (18)	C14—C13—H13	119.4
Ca—O3—C11	166.6 (2)	C12—C13—H13	120.2
O2—C11—O3	122.6 (3)	C13—C14—H14	122.7
O2—C11—C12	117.7 (3)	C15—C14—H14	117.2
O3—C11—C12	119.6 (3)	C16—C15—H15	118.9
C11—C12—C13	121.0 (3)	C14—C15—H15	121.4
C11—C12—C17	119.8 (3)	C15—C16—H16	119.1
C13—C12—C17	119.2 (3)	C17—C16—H16	120.3
C12—C13—C14	120.3 (3)	C16—C17—H17	120.0
C13—C14—C15	120.1 (3)	C12—C17—H17	119.6
C14—C15—C16	119.7 (3)	C19—C20—H20	119.1
C15—C16—C17	120.6 (3)	C21—C20—H20	120.2
C12—C17—C16	120.0 (3)	C22—C21—H21	121.5
Zn—O4—C18	126.02 (19)	C20—C21—H21	119.4
Ca—O5—C18	150.7 (2)	C23—C22—H22	117.8
O4—C18—O5	124.9 (3)	C21—C22—H22	121.3
O4—C18—C19	115.9 (2)	C22—C23—H23	121.2
O5—C18—C19	119.2 (3)	C24—C23—H23	118.8
C18—C19—C20	119.5 (3)	C23—C24—H24	119.2
C18—C19—C24	121.1 (3)	C19—C24—H24	120.7
C20—C19—C24	119.4 (3)	C28—C27—H27	120.4
C19—C20—C21	120.6 (3)	C26—C27—H27	119.6
C20—C21—C22	119.1 (3)	C29—C28—H28	119.4
C21—C22—C23	120.7 (3)	C27—C28—H28	119.9
C22—C23—C24	120.0 (3)	C28—C29—H29	120.2
C19—C24—C23	120.1 (3)	C30—C29—H29	119.6
Zn—O6—C25	124.59 (19)	C29—C30—H30	119.7
Ca—O7—C25	150.8 (2)	C31—C30—H30	119.8
O6—C25—O7	124.7 (3)	C30—C31—H31	119.6
O6—C25—C26	115.9 (2)	C26—C31—H31	119.9

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[CaZn₂(C₇H₅O₂)₆(C₁₀H₁₄N₂O)₂]
M_r	1253.94
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	160
a, b, c (Å)	16.347 (2), 10.7691 (13), 17.647 (2)
β (°)	107.207 (3)
V (Å³)	2967.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Siemens SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SHELXTL; Sheldrick, 1997)
T_min, T_max	0.860, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	12317, 4938, 4193
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.12
No. of reflections	4938
No. of parameters	376
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.48

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXTL (Sheldrick, 1997), SHELXTL and local programs.

Selected geometric parameters (Å, º) top

Zn—N1	2.077 (2)	O2—C11	1.277 (3)
Zn—O2	1.942 (2)	O3—C11	1.242 (3)
Zn—O4	1.959 (2)	O4—C18	1.276 (3)
Zn—O6	1.943 (2)	O5—C18	1.238 (3)
Ca—O3	2.273 (2)	O6—C25	1.275 (4)
Ca—O5	2.316 (2)	O7—C25	1.243 (3)
Ca—O7	2.311 (2)

N1—Zn—O2	96.04 (9)	O5—Ca—O7	85.49 (8)
N1—Zn—O4	95.55 (9)	Zn—O2—C11	112.66 (18)
N1—Zn—O6	97.64 (9)	Ca—O3—C11	166.6 (2)
O2—Zn—O4	126.44 (9)	Zn—O4—C18	126.02 (19)
O2—Zn—O6	125.51 (9)	Ca—O5—C18	150.7 (2)
O4—Zn—O6	104.28 (9)	Zn—O6—C25	124.59 (19)
O3—Ca—O5	88.06 (8)	Ca—O7—C25	150.8 (2)
O3—Ca—O7	88.09 (8)

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