Bis{2-[(2-amino­phen­yl)imino­meth­yl]-6-carboxy­phenolato-κ³O,N,N′}zinc(II)

The title compound, [Zn(C₁₄H₁₇N₂O₃)₂], is a complex of Zn^II and the Schiff base 2-[(2-amino­phen­yl)imino­meth­yl]-6-carboxy­phenol synthesized by the reaction of 3-carboxyl­salicylaldehyde and (1R,2R)-diamino­cyclo­hexane in equimolar ratio. In the crystal structure, the Zn^II ion is six-coordinated in an octa­hedral environment (N₄O₂) formed by two monovalent anions. Each anion acts as a tridentate NON-chelator and occupies a coordination plane. The two NON coordination planes formed are nearly perpendicular to each other.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.055
• wR factor = 0.130
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.88
           From the CIF: _reflns_number_total               6561
           Count of symmetry unique reflns         3760
           Completeness (_total/calc)            174.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2801
           Fraction of Friedel pairs measured     0.745
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          R
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       1.93

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

   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

Bis{2-[(2-aminophenyl)iminomethyl]-6-carboxyphenolato-κ³O,N,N'}zinc(II)

Crystal data

[Zn(C14H17N2O3)2]	F(000) = 1232
Mr = 587.96	Dx = 1.398 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2602 reflections
a = 8.858 (2) Å	θ = 2.4–21.2°
b = 12.610 (3) Å	µ = 0.93 mm^−1
c = 25.008 (6) Å	T = 273 K
V = 2793.5 (11) Å^3	Block, yellow
Z = 4	0.15 × 0.12 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	6561 independent reflections
Radiation source: fine-focus sealed tube	3447 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
ω scans	θmax = 27.9°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→11
Tmin = 0.873, Tmax = 0.905	k = −16→14
17440 measured reflections	l = −32→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0465P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
6561 reflections	Δρmax = 0.52 e Å^−3
354 parameters	Δρmin = −0.50 e Å^−3
0 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.018 (17)

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	0.62507 (7)	0.22595 (5)	0.80851 (2)	0.04202 (17)
N1	0.8183 (5)	0.1449 (3)	0.84129 (15)	0.0448 (11)
H1A	0.8481	0.0934	0.8187	0.054*
H1B	0.8951	0.1909	0.8453	0.054*
N2	0.5171 (5)	0.1326 (3)	0.86837 (15)	0.0363 (10)
N3	0.6222 (6)	0.1380 (3)	0.73562 (13)	0.0509 (11)
H3A	0.7020	0.0938	0.7347	0.061*
H3B	0.5376	0.0986	0.7340	0.061*
N4	0.7148 (4)	0.3406 (3)	0.75455 (15)	0.0396 (10)
O1	0.0832 (4)	0.4874 (3)	0.74804 (16)	0.0685 (12)
O2	0.2787 (5)	0.3884 (3)	0.72568 (14)	0.0670 (11)
H2	0.3351	0.3451	0.7397	0.100*
O3	0.3916 (4)	0.2618 (3)	0.78762 (11)	0.0484 (9)
O4	0.7145 (5)	0.4948 (4)	1.00615 (14)	0.0704 (13)
O5	0.6289 (7)	0.3534 (3)	0.96362 (13)	0.0783 (13)
H5	0.6177	0.3333	0.9327	0.117*
O6	0.6363 (5)	0.3467 (3)	0.86480 (12)	0.0552 (10)
C1	0.2850 (5)	0.2358 (4)	0.87470 (17)	0.0416 (12)
C2	0.2884 (5)	0.2875 (4)	0.82434 (17)	0.0395 (12)
C3	0.1769 (5)	0.3642 (4)	0.8127 (2)	0.0401 (11)
C4	0.0709 (6)	0.3929 (4)	0.8516 (2)	0.0478 (14)
H4	0.0013	0.4461	0.8442	0.057*
C5	0.0683 (6)	0.3426 (5)	0.9011 (2)	0.0595 (16)
H5A	−0.0038	0.3611	0.9265	0.071*
C6	0.1738 (5)	0.2650 (5)	0.91213 (19)	0.0508 (14)
H6	0.1713	0.2312	0.9452	0.061*
C7	0.1746 (6)	0.4172 (4)	0.7600 (2)	0.0480 (14)
C8	0.3933 (6)	0.1545 (4)	0.89157 (18)	0.0432 (12)
H8	0.3693	0.1155	0.9220	0.052*
C9	0.6187 (6)	0.0498 (4)	0.89023 (17)	0.0395 (11)
H9	0.6223	−0.0081	0.8642	0.047*
C10	0.5739 (6)	0.0016 (4)	0.9443 (2)	0.0528 (15)
H10A	0.5695	0.0572	0.9711	0.063*
H10B	0.4744	−0.0300	0.9415	0.063*
C11	0.6876 (7)	−0.0828 (5)	0.9617 (3)	0.0725 (19)
H11A	0.6889	−0.1402	0.9359	0.087*
H11B	0.6582	−0.1118	0.9961	0.087*
C12	0.8450 (7)	−0.0334 (5)	0.9659 (2)	0.077 (2)
H12A	0.8448	0.0209	0.9933	0.092*
H12B	0.9174	−0.0874	0.9761	0.092*
C13	0.8916 (7)	0.0150 (5)	0.9132 (2)	0.0610 (15)
H13A	0.9002	−0.0406	0.8865	0.073*
H13B	0.9901	0.0478	0.9171	0.073*
C14	0.7792 (6)	0.0979 (4)	0.89375 (19)	0.0451 (14)
H14	0.7767	0.1554	0.9202	0.054*
C15	0.7229 (5)	0.4950 (4)	0.8132 (2)	0.0410 (12)
C16	0.6859 (6)	0.4461 (4)	0.86243 (19)	0.0379 (13)
C17	0.7066 (6)	0.5021 (4)	0.91038 (19)	0.0438 (13)
C18	0.7526 (7)	0.6079 (5)	0.9086 (2)	0.0620 (16)
H18	0.7663	0.6449	0.9405	0.074*
C19	0.7781 (7)	0.6585 (5)	0.8608 (2)	0.0653 (17)
H19	0.8038	0.7300	0.8603	0.078*
C20	0.7653 (6)	0.6024 (4)	0.8136 (2)	0.0571 (14)
H20	0.7852	0.6365	0.7814	0.068*
C21	0.6840 (6)	0.4527 (5)	0.9637 (2)	0.0537 (15)
C22	0.7345 (6)	0.4405 (4)	0.76218 (18)	0.0431 (13)
H22	0.7583	0.4814	0.7324	0.052*
C23	0.7486 (6)	0.2945 (4)	0.70063 (17)	0.0437 (13)
H23	0.8452	0.2572	0.7038	0.052*
C24	0.7635 (7)	0.3698 (5)	0.65427 (19)	0.0636 (17)
H24A	0.8460	0.4185	0.6611	0.076*
H24B	0.6715	0.4111	0.6511	0.076*
C25	0.7926 (8)	0.3114 (5)	0.60163 (19)	0.0709 (19)
H25A	0.7960	0.3622	0.5726	0.085*
H25B	0.8899	0.2762	0.6034	0.085*
C26	0.6717 (7)	0.2305 (5)	0.5905 (2)	0.0729 (19)
H26A	0.6960	0.1922	0.5580	0.087*
H26B	0.5758	0.2662	0.5852	0.087*
C27	0.6581 (7)	0.1529 (5)	0.63670 (18)	0.0594 (17)
H27A	0.7508	0.1124	0.6396	0.071*
H27B	0.5764	0.1037	0.6295	0.071*
C28	0.6278 (6)	0.2098 (3)	0.68954 (17)	0.0444 (11)
H28	0.5299	0.2455	0.6868	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0465 (3)	0.0401 (3)	0.0395 (3)	−0.0007 (3)	0.0037 (3)	0.0022 (3)
N1	0.046 (3)	0.039 (3)	0.049 (2)	−0.003 (2)	0.002 (2)	−0.002 (2)
N2	0.033 (3)	0.037 (3)	0.039 (2)	0.004 (2)	−0.002 (2)	0.002 (2)
N3	0.051 (3)	0.051 (3)	0.051 (2)	−0.003 (3)	0.003 (3)	0.001 (2)
N4	0.039 (3)	0.046 (3)	0.033 (2)	−0.008 (2)	0.001 (2)	−0.004 (2)
O1	0.054 (3)	0.068 (3)	0.083 (3)	0.010 (2)	−0.001 (2)	0.030 (2)
O2	0.072 (3)	0.074 (3)	0.055 (2)	0.024 (2)	0.007 (2)	0.021 (2)
O3	0.046 (2)	0.059 (2)	0.0393 (16)	0.001 (2)	0.0019 (16)	0.0059 (15)
O4	0.073 (3)	0.097 (3)	0.042 (2)	0.004 (3)	−0.008 (2)	−0.015 (2)
O5	0.129 (4)	0.063 (3)	0.043 (2)	−0.010 (3)	0.004 (3)	−0.0006 (19)
O6	0.082 (3)	0.038 (2)	0.0452 (19)	−0.008 (2)	0.010 (2)	−0.0005 (16)
C1	0.038 (3)	0.044 (3)	0.042 (3)	0.006 (3)	0.001 (2)	0.005 (2)
C2	0.038 (3)	0.037 (3)	0.043 (3)	0.000 (3)	0.003 (2)	0.001 (2)
C3	0.035 (3)	0.038 (3)	0.047 (3)	−0.003 (2)	−0.003 (3)	0.009 (3)
C4	0.037 (3)	0.050 (4)	0.056 (3)	0.010 (3)	−0.002 (3)	0.012 (3)
C5	0.047 (4)	0.075 (4)	0.057 (4)	0.011 (3)	0.010 (3)	0.005 (3)
C6	0.044 (3)	0.062 (4)	0.047 (3)	0.006 (3)	0.003 (2)	0.008 (3)
C7	0.033 (3)	0.051 (4)	0.060 (4)	−0.005 (3)	0.001 (3)	0.000 (3)
C8	0.040 (3)	0.045 (3)	0.044 (3)	0.008 (3)	0.001 (3)	0.007 (2)
C9	0.039 (3)	0.033 (3)	0.046 (3)	0.008 (3)	−0.004 (3)	0.002 (2)
C10	0.049 (4)	0.050 (4)	0.060 (3)	0.007 (3)	0.004 (3)	0.018 (3)
C11	0.057 (4)	0.070 (5)	0.090 (5)	0.003 (3)	0.000 (4)	0.035 (4)
C12	0.066 (5)	0.084 (5)	0.081 (4)	0.016 (4)	−0.008 (4)	0.036 (4)
C13	0.047 (4)	0.068 (4)	0.068 (4)	0.011 (3)	−0.001 (3)	0.011 (3)
C14	0.044 (3)	0.054 (4)	0.037 (3)	0.004 (3)	−0.002 (3)	0.004 (2)
C15	0.036 (3)	0.045 (3)	0.043 (3)	0.007 (2)	0.000 (3)	0.006 (3)
C16	0.037 (3)	0.038 (3)	0.039 (3)	0.011 (2)	−0.001 (2)	−0.003 (2)
C17	0.035 (3)	0.047 (4)	0.049 (3)	0.008 (3)	−0.006 (3)	−0.005 (3)
C18	0.073 (4)	0.055 (4)	0.058 (4)	0.003 (3)	−0.009 (3)	−0.016 (3)
C19	0.067 (4)	0.043 (4)	0.086 (5)	−0.001 (3)	−0.003 (4)	−0.010 (4)
C20	0.065 (4)	0.046 (3)	0.060 (3)	0.003 (3)	−0.003 (3)	0.006 (3)
C21	0.049 (4)	0.070 (4)	0.042 (3)	0.017 (3)	0.001 (3)	−0.004 (3)
C22	0.044 (3)	0.049 (4)	0.036 (3)	0.000 (3)	0.001 (2)	0.007 (3)
C23	0.040 (3)	0.050 (3)	0.041 (3)	−0.005 (2)	0.001 (2)	−0.002 (2)
C24	0.075 (5)	0.073 (4)	0.042 (3)	−0.021 (4)	0.008 (3)	0.007 (3)
C25	0.086 (5)	0.085 (5)	0.042 (3)	−0.011 (4)	0.012 (3)	0.008 (3)
C26	0.084 (5)	0.090 (5)	0.044 (3)	0.007 (4)	0.007 (3)	0.001 (3)
C27	0.058 (4)	0.070 (4)	0.051 (3)	−0.001 (3)	−0.001 (3)	−0.017 (3)
C28	0.045 (3)	0.050 (3)	0.038 (2)	0.003 (3)	0.007 (3)	−0.005 (3)

Geometric parameters (Å, º)

Zn1—O6	2.076 (3)	C10—H10A	0.9700
Zn1—N4	2.131 (4)	C10—H10B	0.9700
Zn1—N2	2.131 (4)	C11—C12	1.531 (9)
Zn1—N3	2.134 (4)	C11—H11A	0.9700
Zn1—N1	2.155 (4)	C11—H11B	0.9700
Zn1—O3	2.180 (3)	C12—C13	1.510 (7)
N1—C14	1.480 (6)	C12—H12A	0.9700
N1—H1A	0.9000	C12—H12B	0.9700
N1—H1B	0.9000	C13—C14	1.523 (7)
N2—C8	1.271 (6)	C13—H13A	0.9700
N2—C9	1.482 (6)	C13—H13B	0.9700
N3—C28	1.466 (5)	C14—H14	0.9800
N3—H3A	0.9000	C15—C20	1.406 (7)
N3—H3B	0.9000	C15—C16	1.415 (6)
N4—C22	1.286 (6)	C15—C22	1.453 (7)
N4—C23	1.499 (5)	C16—C17	1.404 (6)
O1—C7	1.236 (6)	C17—C18	1.396 (7)
O2—C7	1.310 (6)	C17—C21	1.485 (7)
O2—H2	0.8200	C18—C19	1.373 (7)
O3—C2	1.336 (5)	C18—H18	0.9300
O4—C21	1.218 (6)	C19—C20	1.381 (7)
O5—C21	1.344 (7)	C19—H19	0.9300
O5—H5	0.8200	C20—H20	0.9300
O6—C16	1.330 (6)	C22—H22	0.9300
C1—C6	1.408 (6)	C23—C24	1.504 (6)
C1—C2	1.419 (6)	C23—C28	1.537 (6)
C1—C8	1.467 (7)	C23—H23	0.9800
C2—C3	1.412 (6)	C24—C25	1.531 (7)
C3—C4	1.398 (6)	C24—H24A	0.9700
C3—C7	1.479 (7)	C24—H24B	0.9700
C4—C5	1.392 (7)	C25—C26	1.505 (8)
C4—H4	0.9300	C25—H25A	0.9700
C5—C6	1.380 (7)	C25—H25B	0.9700
C5—H5A	0.9300	C26—C27	1.517 (7)
C6—H6	0.9300	C26—H26A	0.9700
C8—H8	0.9300	C26—H26B	0.9700
C9—C10	1.535 (6)	C27—C28	1.527 (6)
C9—C14	1.548 (7)	C27—H27A	0.9700
C9—H9	0.9800	C27—H27B	0.9700
C10—C11	1.529 (7)	C28—H28	0.9800
O6—Zn1—N4	85.07 (14)	C13—C12—C11	110.8 (5)
O6—Zn1—N2	87.16 (14)	C13—C12—H12A	109.5
N4—Zn1—N2	170.69 (16)	C11—C12—H12A	109.5
O6—Zn1—N3	163.95 (14)	C13—C12—H12B	109.5
N4—Zn1—N3	79.40 (15)	C11—C12—H12B	109.5
N2—Zn1—N3	107.90 (15)	H12A—C12—H12B	108.1
O6—Zn1—N1	92.97 (15)	C12—C13—C14	112.2 (5)
N4—Zn1—N1	105.46 (15)	C12—C13—H13A	109.2
N2—Zn1—N1	80.05 (15)	C14—C13—H13A	109.2
N3—Zn1—N1	95.03 (16)	C12—C13—H13B	109.2
O6—Zn1—O3	93.21 (15)	C14—C13—H13B	109.2
N4—Zn1—O3	93.51 (13)	H13A—C13—H13B	107.9
N2—Zn1—O3	81.79 (14)	N1—C14—C13	113.8 (4)
N3—Zn1—O3	83.79 (15)	N1—C14—C9	108.7 (4)
N1—Zn1—O3	160.48 (14)	C13—C14—C9	110.5 (4)
C14—N1—Zn1	109.9 (3)	N1—C14—H14	107.9
C14—N1—H1A	109.7	C13—C14—H14	107.9
Zn1—N1—H1A	109.7	C9—C14—H14	107.9
C14—N1—H1B	109.7	C20—C15—C16	118.3 (5)
Zn1—N1—H1B	109.7	C20—C15—C22	116.4 (5)
H1A—N1—H1B	108.2	C16—C15—C22	125.1 (4)
C8—N2—C9	120.6 (4)	O6—C16—C17	118.7 (4)
C8—N2—Zn1	126.0 (4)	O6—C16—C15	121.7 (4)
C9—N2—Zn1	112.0 (3)	C17—C16—C15	119.6 (5)
C28—N3—Zn1	110.5 (3)	C18—C17—C16	119.5 (5)
C28—N3—H3A	109.6	C18—C17—C21	117.9 (5)
Zn1—N3—H3A	109.6	C16—C17—C21	122.5 (5)
C28—N3—H3B	109.6	C19—C18—C17	121.3 (5)
Zn1—N3—H3B	109.6	C19—C18—H18	119.4
H3A—N3—H3B	108.1	C17—C18—H18	119.4
C22—N4—C23	119.1 (4)	C18—C19—C20	119.5 (5)
C22—N4—Zn1	128.4 (3)	C18—C19—H19	120.2
C23—N4—Zn1	112.4 (3)	C20—C19—H19	120.2
C7—O2—H2	109.5	C19—C20—C15	121.5 (5)
C2—O3—Zn1	122.3 (3)	C19—C20—H20	119.3
C21—O5—H5	109.5	C15—C20—H20	119.3
C16—O6—Zn1	132.6 (3)	O4—C21—O5	119.2 (5)
C6—C1—C2	119.0 (5)	O4—C21—C17	124.8 (6)
C6—C1—C8	116.7 (4)	O5—C21—C17	116.0 (5)
C2—C1—C8	124.3 (4)	N4—C22—C15	125.7 (5)
O3—C2—C3	120.2 (4)	N4—C22—H22	117.1
O3—C2—C1	120.9 (4)	C15—C22—H22	117.1
C3—C2—C1	118.8 (4)	N4—C23—C24	117.8 (4)
C4—C3—C2	120.3 (4)	N4—C23—C28	107.0 (4)
C4—C3—C7	119.5 (4)	C24—C23—C28	111.1 (4)
C2—C3—C7	120.2 (5)	N4—C23—H23	106.8
C5—C4—C3	120.8 (5)	C24—C23—H23	106.8
C5—C4—H4	119.6	C28—C23—H23	106.8
C3—C4—H4	119.6	C23—C24—C25	111.9 (5)
C6—C5—C4	119.3 (5)	C23—C24—H24A	109.2
C6—C5—H5A	120.4	C25—C24—H24A	109.2
C4—C5—H5A	120.4	C23—C24—H24B	109.2
C5—C6—C1	121.8 (5)	C25—C24—H24B	109.2
C5—C6—H6	119.1	H24A—C24—H24B	107.9
C1—C6—H6	119.1	C26—C25—C24	111.4 (5)
O1—C7—O2	120.1 (5)	C26—C25—H25A	109.4
O1—C7—C3	123.2 (5)	C24—C25—H25A	109.4
O2—C7—C3	116.6 (5)	C26—C25—H25B	109.4
N2—C8—C1	125.8 (4)	C24—C25—H25B	109.4
N2—C8—H8	117.1	H25A—C25—H25B	108.0
C1—C8—H8	117.1	C25—C26—C27	110.7 (4)
N2—C9—C10	116.5 (4)	C25—C26—H26A	109.5
N2—C9—C14	107.6 (4)	C27—C26—H26A	109.5
C10—C9—C14	110.0 (4)	C25—C26—H26B	109.5
N2—C9—H9	107.4	C27—C26—H26B	109.5
C10—C9—H9	107.4	H26A—C26—H26B	108.1
C14—C9—H9	107.4	C26—C27—C28	111.7 (5)
C11—C10—C9	110.9 (4)	C26—C27—H27A	109.3
C11—C10—H10A	109.5	C28—C27—H27A	109.3
C9—C10—H10A	109.5	C26—C27—H27B	109.3
C11—C10—H10B	109.5	C28—C27—H27B	109.3
C9—C10—H10B	109.5	H27A—C27—H27B	107.9
H10A—C10—H10B	108.1	N3—C28—C27	113.3 (4)
C10—C11—C12	109.6 (5)	N3—C28—C23	108.1 (4)
C10—C11—H11A	109.8	C27—C28—C23	111.1 (4)
C12—C11—H11A	109.8	N3—C28—H28	108.0
C10—C11—H11B	109.8	C27—C28—H28	108.0
C12—C11—H11B	109.8	C23—C28—H28	108.0
H11A—C11—H11B	108.2
O6—Zn1—N1—C14	70.4 (3)	C2—C1—C8—N2	12.9 (8)
N4—Zn1—N1—C14	156.1 (3)	C8—N2—C9—C10	−5.9 (7)
N2—Zn1—N1—C14	−16.2 (3)	Zn1—N2—C9—C10	161.4 (3)
N3—Zn1—N1—C14	−123.5 (3)	C8—N2—C9—C14	−129.9 (5)
O3—Zn1—N1—C14	−37.9 (6)	Zn1—N2—C9—C14	37.3 (4)
O6—Zn1—N2—C8	60.4 (4)	N2—C9—C10—C11	179.5 (4)
N3—Zn1—N2—C8	−113.9 (4)	C14—C9—C10—C11	−57.6 (6)
N1—Zn1—N2—C8	153.9 (4)	C9—C10—C11—C12	58.8 (6)
O3—Zn1—N2—C8	−33.2 (4)	C10—C11—C12—C13	−57.9 (7)
O6—Zn1—N2—C9	−106.0 (3)	C11—C12—C13—C14	57.1 (7)
N3—Zn1—N2—C9	79.6 (3)	Zn1—N1—C14—C13	164.3 (4)
N1—Zn1—N2—C9	−12.5 (3)	Zn1—N1—C14—C9	40.8 (5)
O3—Zn1—N2—C9	160.3 (3)	C12—C13—C14—N1	−178.1 (5)
O6—Zn1—N3—C28	−5.3 (9)	C12—C13—C14—C9	−55.5 (6)
N4—Zn1—N3—C28	−20.1 (3)	N2—C9—C14—N1	−51.4 (5)
N2—Zn1—N3—C28	153.9 (3)	C10—C9—C14—N1	−179.3 (4)
N1—Zn1—N3—C28	−124.9 (4)	N2—C9—C14—C13	−176.9 (4)
O3—Zn1—N3—C28	74.7 (3)	C10—C9—C14—C13	55.1 (5)
O6—Zn1—N4—C22	−8.5 (5)	Zn1—O6—C16—C17	−167.3 (4)
N3—Zn1—N4—C22	167.4 (5)	Zn1—O6—C16—C15	10.5 (7)
N1—Zn1—N4—C22	−100.3 (5)	C20—C15—C16—O6	176.0 (5)
O3—Zn1—N4—C22	84.4 (4)	C22—C15—C16—O6	−10.1 (8)
O6—Zn1—N4—C23	175.1 (3)	C20—C15—C16—C17	−6.2 (7)
N3—Zn1—N4—C23	−8.9 (3)	C22—C15—C16—C17	167.7 (5)
N1—Zn1—N4—C23	83.4 (3)	O6—C16—C17—C18	−177.4 (5)
O3—Zn1—N4—C23	−91.9 (3)	C15—C16—C17—C18	4.7 (7)
O6—Zn1—O3—C2	−40.5 (4)	O6—C16—C17—C21	3.8 (7)
N4—Zn1—O3—C2	−125.8 (4)	C15—C16—C17—C21	−174.1 (5)
N2—Zn1—O3—C2	46.1 (3)	C16—C17—C18—C19	0.1 (9)
N3—Zn1—O3—C2	155.3 (4)	C21—C17—C18—C19	179.0 (5)
N1—Zn1—O3—C2	67.7 (6)	C17—C18—C19—C20	−3.3 (9)
N4—Zn1—O6—C16	−2.2 (5)	C18—C19—C20—C15	1.7 (9)
N2—Zn1—O6—C16	−177.0 (5)	C16—C15—C20—C19	3.1 (8)
N3—Zn1—O6—C16	−16.8 (10)	C22—C15—C20—C19	−171.4 (5)
N1—Zn1—O6—C16	103.1 (5)	C18—C17—C21—O4	−6.3 (8)
O3—Zn1—O6—C16	−95.4 (5)	C16—C17—C21—O4	172.5 (5)
Zn1—O3—C2—C3	143.3 (4)	C18—C17—C21—O5	175.2 (5)
Zn1—O3—C2—C1	−39.2 (6)	C16—C17—C21—O5	−5.9 (8)
C6—C1—C2—O3	−179.7 (5)	C23—N4—C22—C15	−172.8 (4)
C8—C1—C2—O3	2.0 (8)	Zn1—N4—C22—C15	11.0 (8)
C6—C1—C2—C3	−2.1 (7)	C20—C15—C22—N4	173.1 (5)
C8—C1—C2—C3	179.6 (4)	C16—C15—C22—N4	−0.9 (8)
O3—C2—C3—C4	−178.6 (4)	C22—N4—C23—C24	−16.2 (7)
C1—C2—C3—C4	3.8 (7)	Zn1—N4—C23—C24	160.5 (4)
O3—C2—C3—C7	−0.5 (7)	C22—N4—C23—C28	−142.2 (4)
C1—C2—C3—C7	−178.1 (4)	Zn1—N4—C23—C28	34.5 (4)
C2—C3—C4—C5	−3.4 (8)	N4—C23—C24—C25	−178.1 (4)
C7—C3—C4—C5	178.5 (5)	C28—C23—C24—C25	−54.2 (6)
C3—C4—C5—C6	1.2 (8)	C23—C24—C25—C26	55.9 (7)
C4—C5—C6—C1	0.5 (8)	C24—C25—C26—C27	−56.1 (7)
C2—C1—C6—C5	0.0 (8)	C25—C26—C27—C28	56.3 (6)
C8—C1—C6—C5	178.4 (5)	Zn1—N3—C28—C27	168.4 (4)
C4—C3—C7—O1	0.5 (8)	Zn1—N3—C28—C23	44.8 (4)
C2—C3—C7—O1	−177.5 (5)	C26—C27—C28—N3	−176.8 (5)
C4—C3—C7—O2	178.7 (5)	C26—C27—C28—C23	−54.9 (6)
C2—C3—C7—O2	0.6 (7)	N4—C23—C28—N3	−51.5 (5)
C9—N2—C8—C1	178.6 (4)	C24—C23—C28—N3	178.6 (4)
Zn1—N2—C8—C1	13.2 (7)	N4—C23—C28—C27	−176.5 (4)
C6—C1—C8—N2	−165.4 (5)	C24—C23—C28—C27	53.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O6	0.82	1.71	2.473 (4)	153
O2—H2···O3	0.82	1.67	2.439 (5)	155
N3—H3A···O1^i	0.90	2.37	3.253 (6)	168
N1—H1A···O1^i	0.90	2.22	3.114 (5)	170

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