{[N,N′-Bis(4-methoxy­benz­yl)ethane-1,2-diyldiimino]diacetato-κ⁴O,N,N′,O′}­bis­(1H-imidazole-κN³)zinc(II)

In the title complex, [Zn(C₂₂H₂₆N₂O₆)(C₃H₄N₂)₂], the Zn^II atom is in a distorted octa­hedral coordination environment defined by the bond lengths and angles formed by an N₄O₂ donor set. In the crystal structure, inter­molecular N—H...O hydrogen bonds link mol­ecules into chains of rings. The atoms of one 4-methoxy­benzyl group are disordered over two sites in approximately a 0.7:0.3 ratio.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.054
• wR factor = 0.147
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C6'

Author Response: This is the minor component of a disordered atom with an occupancy of 0.294(8) therefore the high Ueq might be expected.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O1'

Author Response: This is the minor component of a disordered atom with an occupancy of 0.294(8) therefore the high Ueq might be expected.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C2'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C5'

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.81
PLAT128_ALERT_4_C Non-standard setting of Space group Pbca    ....    Pcab
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.85 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3

Author Response: This is the minor component of a disordered atom with an occupancy of 0.294(8) therefore the high Ueq might be expected.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4

Author Response: This is the minor component of a disordered atom with an occupancy of 0.294(8) therefore the high Ueq might be expected.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      98.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         53

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

This work is a part of a study of the synthesis and structural characterization of metal complexes with the [N,N'-bis(4-methoxybenzyl) ethane-1,2-diyldiimino]diacetate ligand. In this paper, we report the structure of a new Zn(II) complex, Zn(L_a)(L_b)₂(L_a=[N,N'-bis(4-methoxybenzyl) ethane-1,2-diyldiimino]diacetate, L_b=imidazole)(1). In (1) (Fig 1), the Zn^II atom is in a distorted octahedral coordination environment defined by a N₄O₂ donor set, from two amine N atoms (N1,N2), two carboxyl O atoms (O2,O5), and two imidazole N atoms (N3, N5). In the crystal structure (Fig 2), C—H···O and N—H···O hydrogen bonds (Table 2) consolidate the crystal packing into a chain of rings.

Related literature

We have recently determined the structure of the Ni^II analog of the title compound (Zhang et al., 2007).

For related literature, see: Suresh et al. (2006).

S2. Experimental

The title complex was prepared according to the literature method (Zhang et al., 2007). Crystals were obtained by slow evaporation (one month) of a methanol solution (15 ml) of the title complex (0.06 g,0.1 mmol).

S3. Refinement

H atoms bound to C atoms were placed in calculated positions and refined in the riding-model approximation, with C—H = 0.93–97Å and U_iso(H) = 1.2U_eq(C) or C—H = 0.96Å and U_iso (H) = 1.5U_eq(C) for the methyl groups. Similarly H atoms bonded to N atoms were refined with N—H = 0.86 Å, and U_iso(H) = 1.2U_eq(N). The atoms of the 4-methoxybenzyl group were refined as disordered over two sites with refined occupancies 0.706 (8) and 0.294 (4) for the major and minor components. The largest peak in the final difference Fourier of 1.278 e A°^-3 is located 1.87Å from atom H11B. During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecules (possibly methanol). Attempts made to model the solvent molecule were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 98 ų containing approximately 18 electrons. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). A similar treatment of disordered solvent molecules was carried out by (Suresh et al., 2006; and references cited threin)

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. Molecular structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of the title compound. Dashed lines denote hydrogen bonds.

{[N,N'-Bis(4-methoxybenzyl)ethane-1,2-diyldiimino]diacetato- κ⁴O,N,N',O'}bis(1H-imidazole-κN³)zinc(II)

Crystal data

[Zn(C22H26N2O6)(C3H4N2)2]	F(000) = 2576
Mr = 615.98	Dx = 1.309 Mg m^−3
Orthorhombic, Pcab	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2ac	Cell parameters from 9349 reflections
a = 15.3277 (6) Å	θ = 2.5–23.3°
b = 16.3989 (6) Å	µ = 0.83 mm^−1
c = 24.8735 (10) Å	T = 299 K
V = 6252.1 (4) Å^3	Block, colorless
Z = 8	0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	6826 independent reflections
Radiation source: fine-focus sealed tube	3459 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
φ and ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.851, Tmax = 0.921	k = −20→20
67264 measured reflections	l = −31→31

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0892P)^2] where P = (Fo^2 + 2Fc^2)/3
6826 reflections	(Δ/σ)max = 0.002
424 parameters	Δρmax = 1.28 e Å^−3
53 restraints	Δρmin = −0.45 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	Occ. (<1)
Zn1	0.872846 (19)	0.15880 (2)	0.249200 (12)	0.05098 (14)
O1	1.0598 (3)	−0.2030 (3)	0.4822 (2)	0.1087 (18)	0.706 (8)
C1	1.1068 (5)	−0.2738 (5)	0.4709 (3)	0.126 (3)	0.706 (8)
H1A	1.0758	−0.3055	0.4447	0.188*	0.706 (8)
H1B	1.1138	−0.3051	0.5032	0.188*	0.706 (8)
H1C	1.1631	−0.2594	0.4569	0.188*	0.706 (8)
C2	1.0426 (3)	−0.1459 (3)	0.4402 (2)	0.0715 (17)	0.706 (8)
C3	1.0004 (4)	−0.0748 (3)	0.45597 (16)	0.108 (3)	0.706 (8)
H3	0.9875	−0.0661	0.4921	0.130*	0.706 (8)
C4	0.9776 (5)	−0.0166 (3)	0.4178 (2)	0.102 (3)	0.706 (8)
H4	0.9494	0.0310	0.4284	0.122*	0.706 (8)
C5	0.9970 (4)	−0.0296 (3)	0.36391 (19)	0.061 (2)	0.706 (8)
C6	1.0391 (3)	−0.1007 (3)	0.34812 (17)	0.0608 (14)	0.706 (8)
H6	1.0521	−0.1094	0.3120	0.073*	0.706 (8)
C7	1.0619 (3)	−0.1589 (2)	0.3863 (2)	0.0652 (17)	0.706 (8)
H7	1.0901	−0.2065	0.3757	0.078*	0.706 (8)
O1'	1.0884 (9)	−0.2337 (7)	0.4386 (5)	0.152 (6)	0.294 (8)
C1'	1.1133 (19)	−0.220 (2)	0.4934 (7)	0.170 (12)	0.294 (8)
H1'1	1.1421	−0.1678	0.4962	0.254*	0.294 (8)
H1'2	1.1522	−0.2620	0.5050	0.254*	0.294 (8)
H1'3	1.0622	−0.2196	0.5158	0.254*	0.294 (8)
C2'	1.0549 (7)	−0.1642 (5)	0.4130 (5)	0.063 (5)	0.294 (8)
C3'	1.0248 (9)	−0.0965 (7)	0.4410 (4)	0.075 (4)	0.294 (8)
H3'	1.0174	−0.0991	0.4781	0.091*	0.294 (8)
C4'	1.0059 (10)	−0.0248 (6)	0.4136 (5)	0.076 (5)	0.294 (8)
H4'	0.9858	0.0206	0.4324	0.091*	0.294 (8)
C5'	1.0169 (11)	−0.0208 (7)	0.3582 (5)	0.050 (4)	0.294 (8)
C6'	1.0470 (11)	−0.0886 (9)	0.3302 (4)	0.124 (8)	0.294 (8)
H6'	1.0543	−0.0859	0.2932	0.148*	0.294 (8)
C7'	1.0659 (8)	−0.1603 (6)	0.3576 (5)	0.092 (6)	0.294 (8)
H7'	1.0860	−0.2056	0.3389	0.110*	0.294 (8)
C8	0.98219 (17)	0.04199 (18)	0.32373 (13)	0.0644 (8)
H8A	1.0013	0.0924	0.3404	0.077*
H8B	1.0181	0.0330	0.2921	0.077*
C9	0.83192 (19)	0.07064 (18)	0.35121 (12)	0.0628 (8)
H9A	0.8630	0.1046	0.3767	0.075*
H9B	0.8157	0.0206	0.3694	0.075*
C10	0.74994 (19)	0.11460 (19)	0.33311 (13)	0.0581 (7)
C11	0.8554 (2)	−0.01970 (18)	0.27802 (14)	0.0645 (8)
H11A	0.7923	−0.0197	0.2802	0.077*
H11B	0.8765	−0.0688	0.2955	0.077*
C12	0.88233 (19)	−0.02103 (18)	0.21974 (14)	0.0663 (9)
H12A	0.9454	−0.0252	0.2175	0.080*
H12B	0.8576	−0.0688	0.2025	0.080*
C13	0.76025 (17)	0.04746 (19)	0.17132 (12)	0.0609 (8)
H13A	0.7231	0.0375	0.2022	0.073*
H13B	0.7442	0.1003	0.1568	0.073*
C14	0.74011 (17)	−0.01576 (18)	0.12971 (12)	0.0576 (7)
C15	0.70541 (19)	−0.09060 (19)	0.14364 (12)	0.0625 (8)
H15	0.6956	−0.1022	0.1797	0.075*
C16	0.68473 (18)	−0.14911 (18)	0.10515 (13)	0.0650 (8)
H16	0.6611	−0.1991	0.1153	0.078*
C17	0.6999 (2)	−0.1316 (2)	0.05166 (13)	0.0669 (8)
C18	0.7343 (2)	−0.0585 (2)	0.03745 (13)	0.0862 (11)
H18	0.7452	−0.0471	0.0014	0.103*
C19	0.7529 (2)	−0.0013 (2)	0.07575 (13)	0.0797 (10)
H19	0.7749	0.0490	0.0650	0.096*
C20	0.6471 (3)	−0.2624 (3)	0.02183 (18)	0.1185 (16)
H20A	0.6910	−0.2961	0.0381	0.178*
H20B	0.6273	−0.2875	−0.0108	0.178*
H20C	0.5989	−0.2564	0.0461	0.178*
C21	0.91426 (18)	0.06929 (18)	0.14722 (12)	0.0636 (8)
H21A	0.8870	0.1059	0.1216	0.076*
H21B	0.9279	0.0188	0.1287	0.076*
C22	0.9984 (2)	0.1077 (2)	0.16797 (13)	0.0632 (8)
C23	1.00997 (18)	0.26933 (18)	0.29940 (11)	0.0565 (7)
H23	1.0477	0.2566	0.2713	0.068*
C24	0.89875 (19)	0.27488 (18)	0.35004 (12)	0.0595 (7)
H24	0.8432	0.2662	0.3639	0.071*
C25	0.9610 (2)	0.32244 (17)	0.37273 (12)	0.0644 (8)
H25	0.9563	0.3521	0.4044	0.077*
C26	0.73884 (17)	0.27658 (18)	0.20333 (11)	0.0549 (7)
H26	0.7033	0.2674	0.2330	0.066*
C27	0.84577 (19)	0.27410 (18)	0.14814 (11)	0.0585 (7)
H27	0.8995	0.2622	0.1326	0.070*
C28	0.7846 (2)	0.32259 (17)	0.12664 (12)	0.0625 (8)
H28	0.7879	0.3498	0.0939	0.075*
N1	0.88931 (14)	0.05132 (14)	0.30650 (9)	0.0537 (6)
N2	0.85342 (14)	0.05256 (14)	0.19088 (9)	0.0531 (6)
N3	0.93063 (14)	0.24140 (13)	0.30321 (9)	0.0503 (6)
N4	1.03098 (16)	0.31812 (15)	0.34020 (10)	0.0626 (7)
H4A	1.0801	0.3424	0.3449	0.075*
N5	0.81647 (14)	0.24446 (13)	0.19703 (8)	0.0494 (6)
N6	0.71714 (15)	0.32427 (14)	0.16178 (10)	0.0604 (6)
H6A	0.6693	0.3510	0.1581	0.072*
O2	0.75060 (12)	0.15092 (11)	0.28925 (7)	0.0597 (5)
O3	0.68863 (15)	0.11563 (16)	0.36534 (9)	0.0894 (8)
O4	0.68267 (16)	−0.18484 (16)	0.01018 (9)	0.0913 (7)
O5	0.99491 (11)	0.14794 (12)	0.21076 (8)	0.0614 (5)
O6	1.06393 (15)	0.09949 (16)	0.13974 (10)	0.0995 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0416 (2)	0.0579 (2)	0.0534 (2)	−0.00057 (15)	−0.00030 (14)	−0.00093 (15)
O1	0.109 (4)	0.127 (4)	0.090 (4)	0.042 (3)	0.007 (3)	0.034 (3)
C1	0.141 (6)	0.131 (7)	0.104 (6)	0.053 (6)	−0.015 (5)	0.045 (5)
C2	0.078 (4)	0.075 (4)	0.062 (4)	0.025 (3)	−0.005 (3)	−0.011 (4)
C3	0.149 (7)	0.109 (5)	0.066 (4)	0.074 (5)	−0.015 (4)	−0.007 (4)
C4	0.113 (7)	0.106 (5)	0.086 (5)	0.057 (4)	−0.051 (4)	−0.012 (4)
C5	0.030 (4)	0.054 (4)	0.100 (6)	−0.005 (3)	−0.011 (3)	0.002 (3)
C6	0.035 (2)	0.055 (3)	0.093 (4)	0.007 (2)	0.009 (2)	0.007 (3)
C7	0.044 (3)	0.068 (4)	0.084 (6)	0.020 (2)	0.005 (3)	0.006 (3)
O1'	0.176 (12)	0.123 (10)	0.157 (13)	0.057 (9)	0.035 (11)	0.066 (10)
C1'	0.166 (14)	0.178 (15)	0.164 (14)	0.014 (10)	0.001 (9)	0.017 (9)
C2'	0.067 (7)	0.054 (7)	0.067 (9)	0.009 (6)	0.000 (6)	−0.005 (6)
C3'	0.096 (8)	0.058 (7)	0.072 (7)	0.044 (6)	0.002 (6)	−0.029 (6)
C4'	0.078 (8)	0.074 (8)	0.075 (8)	0.047 (6)	−0.010 (6)	−0.018 (7)
C5'	0.027 (6)	0.055 (7)	0.069 (7)	−0.019 (5)	0.002 (5)	−0.003 (6)
C6'	0.121 (11)	0.108 (11)	0.142 (11)	0.014 (8)	0.015 (8)	0.018 (8)
C7'	0.090 (8)	0.095 (8)	0.091 (8)	0.008 (6)	−0.002 (6)	−0.002 (6)
C8	0.0454 (17)	0.067 (2)	0.081 (2)	0.0041 (15)	−0.0143 (15)	0.0021 (17)
C9	0.0549 (19)	0.073 (2)	0.0608 (19)	0.0061 (15)	0.0032 (16)	0.0126 (16)
C10	0.0509 (18)	0.0616 (19)	0.062 (2)	0.0048 (14)	0.0054 (15)	0.0128 (16)
C11	0.0653 (19)	0.0550 (19)	0.073 (2)	−0.0045 (15)	−0.0095 (16)	0.0015 (17)
C12	0.062 (2)	0.065 (2)	0.072 (2)	0.0006 (16)	−0.0128 (16)	−0.0070 (17)
C13	0.0399 (15)	0.074 (2)	0.0686 (19)	−0.0006 (14)	−0.0069 (14)	−0.0111 (16)
C14	0.0423 (16)	0.071 (2)	0.0596 (19)	−0.0053 (15)	−0.0056 (14)	−0.0067 (16)
C15	0.0515 (17)	0.084 (2)	0.0520 (18)	−0.0102 (16)	−0.0007 (14)	−0.0027 (16)
C16	0.0485 (17)	0.073 (2)	0.074 (2)	−0.0130 (15)	−0.0007 (16)	−0.0053 (17)
C17	0.0559 (19)	0.084 (2)	0.061 (2)	−0.0030 (17)	−0.0037 (15)	−0.0150 (18)
C18	0.102 (3)	0.106 (3)	0.0504 (19)	−0.037 (2)	−0.0023 (19)	−0.001 (2)
C19	0.091 (3)	0.081 (2)	0.066 (2)	−0.0291 (19)	−0.0129 (19)	0.0095 (19)
C20	0.155 (4)	0.097 (3)	0.104 (4)	−0.035 (3)	−0.018 (3)	−0.025 (3)
C21	0.0512 (18)	0.073 (2)	0.067 (2)	−0.0071 (15)	0.0017 (15)	−0.0204 (16)
C22	0.0516 (19)	0.071 (2)	0.067 (2)	−0.0018 (16)	0.0056 (16)	−0.0123 (17)
C23	0.0519 (18)	0.0651 (19)	0.0526 (18)	−0.0026 (15)	0.0053 (14)	−0.0067 (15)
C24	0.0548 (17)	0.0640 (19)	0.0597 (19)	0.0039 (16)	0.0062 (15)	−0.0003 (16)
C25	0.073 (2)	0.065 (2)	0.0554 (19)	0.0057 (17)	0.0048 (17)	−0.0060 (15)
C26	0.0473 (17)	0.0606 (18)	0.0568 (18)	−0.0018 (14)	0.0042 (14)	0.0077 (15)
C27	0.0533 (17)	0.0663 (19)	0.0558 (19)	−0.0067 (16)	0.0095 (15)	−0.0013 (15)
C28	0.067 (2)	0.070 (2)	0.0514 (18)	−0.0135 (16)	−0.0019 (16)	0.0087 (15)
N1	0.0449 (13)	0.0547 (14)	0.0616 (15)	−0.0004 (11)	−0.0081 (12)	0.0006 (12)
N2	0.0444 (13)	0.0610 (15)	0.0540 (14)	−0.0020 (11)	0.0007 (11)	−0.0074 (12)
N3	0.0420 (13)	0.0561 (14)	0.0530 (14)	0.0007 (11)	0.0013 (11)	−0.0030 (11)
N4	0.0559 (15)	0.0636 (16)	0.0684 (17)	−0.0061 (12)	−0.0052 (13)	−0.0045 (13)
N5	0.0448 (13)	0.0556 (14)	0.0478 (14)	−0.0018 (11)	−0.0008 (11)	0.0030 (10)
N6	0.0473 (14)	0.0643 (16)	0.0694 (17)	−0.0009 (12)	−0.0029 (12)	0.0085 (13)
O2	0.0492 (11)	0.0718 (13)	0.0581 (12)	0.0055 (9)	0.0036 (9)	0.0159 (10)
O3	0.0672 (15)	0.1196 (19)	0.0814 (17)	0.0266 (14)	0.0225 (13)	0.0384 (14)
O4	0.106 (2)	0.1000 (18)	0.0676 (15)	−0.0186 (16)	−0.0063 (13)	−0.0219 (14)
O5	0.0448 (11)	0.0736 (14)	0.0658 (13)	−0.0060 (9)	0.0019 (9)	−0.0164 (11)
O6	0.0589 (14)	0.135 (2)	0.105 (2)	−0.0228 (14)	0.0235 (14)	−0.0598 (16)

Geometric parameters (Å, º)

Zn1—N5	2.099 (2)	C11—H11A	0.9700
Zn1—N3	2.103 (2)	C11—H11B	0.9700
Zn1—O5	2.1086 (18)	C12—N2	1.472 (4)
Zn1—O2	2.1261 (18)	C12—H12A	0.9700
Zn1—N1	2.281 (2)	C12—H12B	0.9700
Zn1—N2	2.287 (2)	C13—C14	1.497 (4)
O1—C1	1.395 (7)	C13—N2	1.511 (3)
O1—C2	1.428 (5)	C13—H13A	0.9700
C1—H1A	0.9600	C13—H13B	0.9700
C1—H1B	0.9600	C14—C19	1.377 (4)
C1—H1C	0.9600	C14—C15	1.382 (4)
C2—C3	1.3900	C15—C16	1.392 (4)
C2—C7	1.3900	C15—H15	0.9300
C3—C4	1.3900	C16—C17	1.381 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.3900	C17—C18	1.357 (4)
C4—H4	0.9300	C17—O4	1.377 (4)
C5—C6	1.3900	C18—C19	1.366 (4)
C5—C8	1.558 (4)	C18—H18	0.9300
C6—C7	1.3900	C19—H19	0.9300
C6—H6	0.9300	C20—O4	1.414 (4)
C7—H7	0.9300	C20—H20A	0.9600
O1'—C2'	1.402 (8)	C20—H20B	0.9600
O1'—C1'	1.435 (10)	C20—H20C	0.9600
C1'—H1'1	0.9600	C21—N2	1.458 (3)
C1'—H1'2	0.9600	C21—C22	1.525 (4)
C1'—H1'3	0.9600	C21—H21A	0.9700
C2'—C3'	1.3900	C21—H21B	0.9700
C2'—C7'	1.3900	C22—O6	1.233 (3)
C3'—C4'	1.3900	C22—O5	1.253 (3)
C3'—H3'	0.9300	C23—N3	1.303 (3)
C4'—C5'	1.3900	C23—N4	1.332 (3)
C4'—H4'	0.9300	C23—H23	0.9300
C5'—C6'	1.3900	C24—C25	1.355 (4)
C5'—C8	1.443 (7)	C24—N3	1.377 (3)
C6'—C7'	1.3900	C24—H24	0.9300
C6'—H6'	0.9300	C25—N4	1.346 (4)
C7'—H7'	0.9300	C25—H25	0.9300
C8—N1	1.495 (3)	C26—N5	1.311 (3)
C8—H8A	0.9700	C26—N6	1.338 (3)
C8—H8B	0.9700	C26—H26	0.9300
C9—N1	1.453 (3)	C27—C28	1.341 (4)
C9—C10	1.517 (4)	C27—N5	1.384 (3)
C9—H9A	0.9700	C27—H27	0.9300
C9—H9B	0.9700	C28—N6	1.354 (3)
C10—O3	1.235 (3)	C28—H28	0.9300
C10—O2	1.243 (3)	N4—H4A	0.8600
C11—N1	1.459 (4)	N6—H6A	0.8600
C11—C12	1.507 (5)
N5—Zn1—N3	97.89 (9)	C11—C12—H12B	109.2
N5—Zn1—O5	98.14 (8)	H12A—C12—H12B	107.9
N3—Zn1—O5	88.30 (8)	C14—C13—N2	117.1 (2)
N5—Zn1—O2	88.14 (8)	C14—C13—H13A	108.0
N3—Zn1—O2	96.37 (8)	N2—C13—H13A	108.0
O5—Zn1—O2	171.62 (8)	C14—C13—H13B	108.0
N5—Zn1—N1	161.68 (8)	N2—C13—H13B	108.0
N3—Zn1—N1	92.98 (8)	H13A—C13—H13B	107.3
O5—Zn1—N1	96.89 (8)	C19—C14—C15	116.9 (3)
O2—Zn1—N1	75.98 (7)	C19—C14—C13	121.7 (3)
N5—Zn1—N2	93.68 (8)	C15—C14—C13	121.4 (3)
N3—Zn1—N2	161.94 (8)	C14—C15—C16	121.8 (3)
O5—Zn1—N2	76.32 (7)	C14—C15—H15	119.1
O2—Zn1—N2	97.83 (8)	C16—C15—H15	119.1
N1—Zn1—N2	79.75 (9)	C17—C16—C15	118.7 (3)
C1—O1—C2	119.5 (6)	C17—C16—H16	120.6
C3—C2—C7	120.0	C15—C16—H16	120.6
C3—C2—O1	115.4 (4)	C18—C17—O4	116.1 (3)
C7—C2—O1	124.5 (4)	C18—C17—C16	120.0 (3)
C4—C3—C2	120.0	O4—C17—C16	123.9 (3)
C4—C3—H3	120.0	C17—C18—C19	120.4 (3)
C2—C3—H3	120.0	C17—C18—H18	119.8
C3—C4—C5	120.0	C19—C18—H18	119.8
C3—C4—H4	120.0	C18—C19—C14	122.1 (3)
C5—C4—H4	120.0	C18—C19—H19	118.9
C4—C5—C6	120.0	C14—C19—H19	118.9
C4—C5—C8	118.2 (3)	O4—C20—H20A	109.5
C6—C5—C8	121.2 (3)	O4—C20—H20B	109.5
C7—C6—C5	120.0	H20A—C20—H20B	109.5
C7—C6—H6	120.0	O4—C20—H20C	109.5
C5—C6—H6	120.0	H20A—C20—H20C	109.5
C6—C7—C2	120.0	H20B—C20—H20C	109.5
C6—C7—H7	120.0	N2—C21—C22	111.5 (2)
C2—C7—H7	120.0	N2—C21—H21A	109.3
C2'—O1'—C1'	113.5 (19)	C22—C21—H21A	109.3
O1'—C1'—H1'1	109.5	N2—C21—H21B	109.3
O1'—C1'—H1'2	109.5	C22—C21—H21B	109.3
H1'1—C1'—H1'2	109.5	H21A—C21—H21B	108.0
O1'—C1'—H1'3	109.5	O6—C22—O5	125.1 (3)
H1'1—C1'—H1'3	109.5	O6—C22—C21	116.8 (3)
H1'2—C1'—H1'3	109.5	O5—C22—C21	118.0 (3)
C3'—C2'—C7'	120.0	N3—C23—N4	112.4 (2)
C3'—C2'—O1'	122.9 (10)	N3—C23—H23	123.8
C7'—C2'—O1'	116.3 (10)	N4—C23—H23	123.8
C2'—C3'—C4'	120.0	C25—C24—N3	109.4 (3)
C2'—C3'—H3'	120.0	C25—C24—H24	125.3
C4'—C3'—H3'	120.0	N3—C24—H24	125.3
C5'—C4'—C3'	120.0	N4—C25—C24	106.3 (3)
C5'—C4'—H4'	120.0	N4—C25—H25	126.9
C3'—C4'—H4'	120.0	C24—C25—H25	126.9
C4'—C5'—C6'	120.0	N5—C26—N6	111.6 (2)
C4'—C5'—C8	125.3 (10)	N5—C26—H26	124.2
C6'—C5'—C8	113.3 (10)	N6—C26—H26	124.2
C5'—C6'—C7'	120.0	C28—C27—N5	109.4 (3)
C5'—C6'—H6'	120.0	C28—C27—H27	125.3
C7'—C6'—H6'	120.0	N5—C27—H27	125.3
C6'—C7'—C2'	120.0	C27—C28—N6	106.8 (3)
C6'—C7'—H7'	120.0	C27—C28—H28	126.6
C2'—C7'—H7'	120.0	N6—C28—H28	126.6
C5'—C8—N1	126.5 (7)	C9—N1—C11	109.3 (2)
N1—C8—C5	113.6 (3)	C9—N1—C8	112.3 (2)
C5'—C8—H8A	104.0	C11—N1—C8	113.4 (2)
N1—C8—H8A	108.9	C9—N1—Zn1	104.05 (17)
C5—C8—H8A	108.9	C11—N1—Zn1	105.91 (17)
C5'—C8—H8B	99.5	C8—N1—Zn1	111.33 (17)
N1—C8—H8B	108.9	C21—N2—C12	109.0 (2)
C5—C8—H8B	108.9	C21—N2—C13	112.0 (2)
H8A—C8—H8B	107.7	C12—N2—C13	113.3 (2)
N1—C9—C10	112.2 (2)	C21—N2—Zn1	104.23 (16)
N1—C9—H9A	109.2	C12—N2—Zn1	106.03 (17)
C10—C9—H9A	109.2	C13—N2—Zn1	111.68 (16)
N1—C9—H9B	109.2	C23—N3—C24	104.6 (2)
C10—C9—H9B	109.2	C23—N3—Zn1	124.95 (19)
H9A—C9—H9B	107.9	C24—N3—Zn1	130.35 (19)
O3—C10—O2	124.7 (3)	C23—N4—C25	107.3 (2)
O3—C10—C9	116.4 (3)	C23—N4—H4A	126.4
O2—C10—C9	118.8 (3)	C25—N4—H4A	126.4
N1—C11—C12	112.4 (2)	C26—N5—C27	105.0 (2)
N1—C11—H11A	109.1	C26—N5—Zn1	124.67 (19)
C12—C11—H11A	109.1	C27—N5—Zn1	130.1 (2)
N1—C11—H11B	109.1	C26—N6—C28	107.3 (2)
C12—C11—H11B	109.1	C26—N6—H6A	126.4
H11A—C11—H11B	107.9	C28—N6—H6A	126.4
N2—C12—C11	112.0 (2)	C10—O2—Zn1	116.58 (18)
N2—C12—H12A	109.2	C17—O4—C20	119.4 (3)
C11—C12—H12A	109.2	C22—O5—Zn1	117.84 (18)
N2—C12—H12B	109.2
C1—O1—C2—C3	−175.9 (6)	N3—Zn1—N1—C8	−54.73 (19)
C1—O1—C2—C7	6.7 (8)	O5—Zn1—N1—C8	33.9 (2)
C7—C2—C3—C4	0.0	O2—Zn1—N1—C8	−150.6 (2)
O1—C2—C3—C4	−177.5 (5)	N2—Zn1—N1—C8	108.6 (2)
C2—C3—C4—C5	0.0	C22—C21—N2—C12	−76.9 (3)
C3—C4—C5—C6	0.0	C22—C21—N2—C13	156.9 (2)
C3—C4—C5—C8	−171.6 (5)	C22—C21—N2—Zn1	36.0 (3)
C4—C5—C6—C7	0.0	C11—C12—N2—C21	151.0 (2)
C8—C5—C6—C7	171.3 (5)	C11—C12—N2—C13	−83.5 (3)
C5—C6—C7—C2	0.0	C11—C12—N2—Zn1	39.4 (3)
C3—C2—C7—C6	0.0	C14—C13—N2—C21	59.1 (3)
O1—C2—C7—C6	177.3 (5)	C14—C13—N2—C12	−64.7 (3)
C1'—O1'—C2'—C3'	−18 (2)	C14—C13—N2—Zn1	175.6 (2)
C1'—O1'—C2'—C7'	152.0 (17)	N5—Zn1—N2—C21	69.48 (18)
C7'—C2'—C3'—C4'	0.0	N3—Zn1—N2—C21	−60.4 (4)
O1'—C2'—C3'—C4'	169.5 (13)	O5—Zn1—N2—C21	−28.01 (17)
C2'—C3'—C4'—C5'	0.0	O2—Zn1—N2—C21	158.10 (17)
C3'—C4'—C5'—C6'	0.0	N1—Zn1—N2—C21	−127.76 (18)
C3'—C4'—C5'—C8	165.5 (14)	N5—Zn1—N2—C12	−175.58 (17)
C4'—C5'—C6'—C7'	0.0	N3—Zn1—N2—C12	54.6 (3)
C8—C5'—C6'—C7'	−167.1 (13)	O5—Zn1—N2—C12	86.93 (17)
C5'—C6'—C7'—C2'	0.0	O2—Zn1—N2—C12	−86.96 (17)
C3'—C2'—C7'—C6'	0.0	N1—Zn1—N2—C12	−12.82 (17)
O1'—C2'—C7'—C6'	−170.1 (12)	N5—Zn1—N2—C13	−51.68 (19)
C4'—C5'—C8—N1	−74.9 (12)	N3—Zn1—N2—C13	178.5 (2)
C6'—C5'—C8—N1	91.5 (9)	O5—Zn1—N2—C13	−149.2 (2)
C4'—C5'—C8—C5	−61 (3)	O2—Zn1—N2—C13	36.94 (19)
C6'—C5'—C8—C5	105 (3)	N1—Zn1—N2—C13	111.07 (19)
C4—C5—C8—C5'	111 (3)	N4—C23—N3—C24	−0.1 (3)
C6—C5—C8—C5'	−60 (3)	N4—C23—N3—Zn1	−177.41 (18)
C4—C5—C8—N1	−80.7 (4)	C25—C24—N3—C23	0.2 (3)
C6—C5—C8—N1	107.9 (4)	C25—C24—N3—Zn1	177.30 (19)
N1—C9—C10—O3	162.8 (3)	N5—Zn1—N3—C23	−91.8 (2)
N1—C9—C10—O2	−21.7 (4)	O5—Zn1—N3—C23	6.2 (2)
N1—C11—C12—N2	−58.1 (3)	O2—Zn1—N3—C23	179.2 (2)
N2—C13—C14—C19	−84.7 (4)	N1—Zn1—N3—C23	103.0 (2)
N2—C13—C14—C15	97.2 (3)	N2—Zn1—N3—C23	37.5 (4)
C19—C14—C15—C16	0.4 (4)	N5—Zn1—N3—C24	91.6 (2)
C13—C14—C15—C16	178.6 (3)	O5—Zn1—N3—C24	−170.4 (2)
C14—C15—C16—C17	0.3 (4)	O2—Zn1—N3—C24	2.6 (2)
C15—C16—C17—C18	−0.1 (5)	N1—Zn1—N3—C24	−73.6 (2)
C15—C16—C17—O4	179.5 (3)	N2—Zn1—N3—C24	−139.1 (3)
O4—C17—C18—C19	179.4 (3)	N3—C23—N4—C25	0.0 (3)
C16—C17—C18—C19	−1.0 (5)	C24—C25—N4—C23	0.2 (3)
C17—C18—C19—C14	1.8 (6)	N6—C26—N5—C27	0.1 (3)
C15—C14—C19—C18	−1.4 (5)	N6—C26—N5—Zn1	−175.02 (17)
C13—C14—C19—C18	−179.7 (3)	C28—C27—N5—C26	−0.3 (3)
N2—C21—C22—O6	156.1 (3)	C28—C27—N5—Zn1	174.41 (19)
N2—C21—C22—O5	−26.9 (4)	N3—Zn1—N5—C26	−87.8 (2)
N3—C24—C25—N4	−0.2 (3)	O5—Zn1—N5—C26	−177.2 (2)
N5—C27—C28—N6	0.4 (3)	O2—Zn1—N5—C26	8.4 (2)
C10—C9—N1—C11	−77.8 (3)	N1—Zn1—N5—C26	38.0 (4)
C10—C9—N1—C8	155.5 (2)	N2—Zn1—N5—C26	106.1 (2)
C10—C9—N1—Zn1	35.0 (3)	N3—Zn1—N5—C27	98.3 (2)
C12—C11—N1—C9	153.2 (2)	O5—Zn1—N5—C27	8.9 (2)
C12—C11—N1—C8	−80.7 (3)	O2—Zn1—N5—C27	−165.5 (2)
C12—C11—N1—Zn1	41.7 (3)	N1—Zn1—N5—C27	−135.8 (3)
C5'—C8—N1—C9	66.0 (8)	N2—Zn1—N5—C27	−67.8 (2)
C5—C8—N1—C9	62.6 (4)	N5—C26—N6—C28	0.2 (3)
C5'—C8—N1—C11	−58.5 (8)	C27—C28—N6—C26	−0.4 (3)
C5—C8—N1—C11	−61.9 (4)	O3—C10—O2—Zn1	167.9 (3)
C5'—C8—N1—Zn1	−177.8 (8)	C9—C10—O2—Zn1	−7.2 (4)
C5—C8—N1—Zn1	178.8 (3)	N5—Zn1—O2—C10	−168.1 (2)
N5—Zn1—N1—C9	−60.0 (3)	N3—Zn1—O2—C10	−70.4 (2)
N3—Zn1—N1—C9	66.46 (18)	N1—Zn1—O2—C10	21.1 (2)
O5—Zn1—N1—C9	155.10 (17)	N2—Zn1—O2—C10	98.4 (2)
O2—Zn1—N1—C9	−29.37 (17)	C18—C17—O4—C20	179.7 (3)
N2—Zn1—N1—C9	−130.20 (18)	C16—C17—O4—C20	0.2 (5)
N5—Zn1—N1—C11	55.2 (3)	O6—C22—O5—Zn1	176.3 (3)
N3—Zn1—N1—C11	−178.36 (18)	C21—C22—O5—Zn1	−0.4 (4)
O5—Zn1—N1—C11	−89.71 (18)	N5—Zn1—O5—C22	−75.3 (2)
O2—Zn1—N1—C11	85.81 (18)	N3—Zn1—O5—C22	−173.1 (2)
N2—Zn1—N1—C11	−15.02 (18)	N1—Zn1—O5—C22	94.2 (2)
N5—Zn1—N1—C8	178.8 (2)	N2—Zn1—O5—C22	16.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O3^i	0.86	1.87	2.722 (3)	171
N6—H6A···O6^ii	0.86	1.86	2.716 (3)	171
C23—H23···O5	0.93	2.47	2.979 (4)	115
C26—H26···O2	0.93	2.48	2.974 (3)	114

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