Bis(benzimidazole-κN)bis­(4-formyl­benzoato-κO)zinc(II) monohydrate

The zinc center in the title compound, [Zn(C₈H₅O₃)₂(C₇H₆N₂)₂]·H₂O, shows tetra­hedral coordination. The mol­ecules are linked by N—H...O and O—H...O hydrogen bonds. One of the two formylbenzoate ligands is disordered, approximately equally, over two positions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.194
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        O2'

Author Response: The carboxylate group is disordered; the --CO~2~ part binds through one oxygen, and the other is free. Both double-bond oxygen atoms have high temperature factors.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O2

Author Response: The carboxylate group is disordered; the --CO~2~ part binds through one oxygen, and the other is free. Both double-bond oxygen atoms have high temperature factors.

PLAT432_ALERT_2_B Short Inter X...Y Contact  O2'    ..  C7'     ..       2.82 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.558     0.843
            Tmin(prime) and Tmax expected:      0.717     0.838
            RR(prime) =      0.774
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

Author Response: The carboxylate group is disordered; the --CO~2~ part binds through one oxygen, and the other is free. Both double-bond oxygen atoms have high temperature factors.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O1'

Author Response: The carboxylate group is disordered; the --CO~2~ part binds through one oxygen, and the other is free. Both double-bond oxygen atoms have high temperature factors.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C7'

Author Response: The carboxylate group is disordered; the --CO~2~ part binds through one oxygen, and the other is free. Both double-bond oxygen atoms have high temperature factors.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C1'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      21.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C30 H24 N4 O7 Zn1
            Atom count from _chemical_formula_moiety:
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        178

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

Bis(4-formylbenzoato)zinc, which exists as a tetrahedral diaqua compound (Deng et al., 2006a), form a five-coordinate aqua complex with phenathroline (Deng et al., 2006b). The title compound is a 1:2 adduct of Bis(4-formylbenzoato)zinc with benzimidazole, crystallizing with a molecule of water (I). The metal center shows tetrahedral coordination (Fig. 1). Adjacent molecules are linked by hydrogen bonds.

Related literature

For the diaqua complex, see Deng et al., 2006a, and for the aqua phenanthroline adduct, see Deng et al., 2006b.

S2. Experimental

Zinc diacetate dihydrate (0.11 g, 0.5 mmol) was added to a 1:1 aqueous-ethanol solution (20 ml) of 4-formylbenzoic acid (0.15 g, 1 mmol) and benzimidazole (0.07 g, 1 mmol). Sodium hydroxide was added to a pH value of about 5. The filtered solution was set aside for the formation of colorless prismatic crystals. CH&N analysis. Calculated for C₃₀H₂₄N₄O₇Zn: C 58.31, H 3.91, N 9.07%. Found: C 58.28, H 3.93, N 9.04%.

S3. Refinement

One of the two formylbenzoate anions is disordered over two positions; the occupancy factors refined to 0.535 (5):0.465 (5). For both components, the phenylene ring was refined as a rigid hexagon of 1.39Å sides. The C–C single-bond length was restrained to 1.50±0.01Å and the C=O double-bond distance to 1.25±0.01 Å. The C_aliphatic···C_ortho distances were restrained to 2.50±0.01 Å and the entire anion was restrained to be planar. As the C8 atom is less than 0.2 Å from C8', the temperature factors were restrained to be identical; those of the O3 and O3' were similarly treated for the same reason. Additionally, the disordered atoms were restrained to be nearly isotropic. A consideration of the hydrogen bonding distances led to pairing the O1w' water molecule with the primed anion.

The carbon- and nitrogen bound H atoms were generated geometrically (C–H 0.93, N–H 0.86 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C). The water H atoms could were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined.

Computing details

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

Figures

Fig. 1. Thermal ellipsoid plot of the molecular structure of (I). Only one of the disorder components is shown. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are drawn as spheres of arbitrary radii.

Bis(benzimidazole-κN)bis(4-formylbenzoato-κO)\ zinc(II) monohydrate

Crystal data

[Zn(C8H5O3)2(C7H6N2)2].H2O	F(000) = 2544
Mr = 617.90	Dx = 1.465 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 13980 reflections
a = 13.7968 (8) Å	θ = 3.1–27.5°
b = 17.0524 (8) Å	µ = 0.93 mm^−1
c = 23.848 (1) Å	T = 295 K
β = 92.954 (1)°	Prism, colourless
V = 5603.1 (5) Å^3	0.35 × 0.26 × 0.19 mm
Z = 8

Data collection

Rigaku RAXIS-RAPID IP diffractometer	6393 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
ω scan	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.558, Tmax = 0.843	k = −21→22
27096 measured reflections	l = −30→30

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.194	w = 1/[σ^2(Fo^2) + (0.0884P)^2 + 4.8786P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
6393 reflections	Δρmax = 0.70 e Å^−3
453 parameters	Δρmin = −0.67 e Å^−3
178 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0008 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.28971 (4)	0.59229 (3)	0.38356 (2)	0.0525 (2)
N1	0.2248 (3)	0.4871 (2)	0.36616 (14)	0.0554 (9)
N2	0.1303 (3)	0.4014 (2)	0.32177 (19)	0.0726 (12)
H2n	0.0868	0.3830	0.2982	0.087*
N3	0.2451 (3)	0.6254 (2)	0.45870 (14)	0.0522 (9)
N4	0.2390 (3)	0.6728 (2)	0.54477 (15)	0.0606 (10)
H4n	0.2587	0.6909	0.5770	0.073*
O4	0.2136 (3)	0.64849 (19)	0.32459 (13)	0.0658 (9)
O5	0.2842 (3)	0.7626 (2)	0.34589 (14)	0.0768 (10)
O6	−0.0635 (3)	0.8200 (3)	0.10574 (17)	0.1046 (15)
O1	0.4180 (6)	0.5925 (4)	0.3560 (4)	0.079 (2)	0.535 (5)
O2	0.4492 (6)	0.5579 (4)	0.4422 (4)	0.103 (3)	0.535 (5)
O3	0.9173 (18)	0.5162 (7)	0.3088 (8)	0.098 (2)	0.535 (5)
O1w	0.4534 (8)	0.7360 (6)	0.2980 (5)	0.141 (4)	0.535 (5)
H1w1	0.4569	0.6904	0.3115	0.169*	0.535 (5)
H1w2	0.4005	0.7568	0.3089	0.169*	0.535 (5)
C1	0.4754 (5)	0.5692 (3)	0.3940 (4)	0.072 (4)	0.535 (5)
C2	0.5795 (4)	0.5542 (3)	0.3815 (3)	0.061 (3)	0.535 (5)
C7	0.6133 (5)	0.5658 (3)	0.3283 (2)	0.054 (3)	0.535 (5)
H7	0.5712	0.5833	0.2992	0.064*	0.535 (5)
C6	0.7101 (5)	0.5513 (4)	0.3184 (3)	0.051 (2)	0.535 (5)
H6	0.7327	0.5590	0.2827	0.061*	0.535 (5)
C5	0.7731 (4)	0.5251 (5)	0.3618 (4)	0.059 (4)	0.535 (5)
C4	0.7393 (5)	0.5135 (5)	0.4150 (3)	0.065 (3)	0.535 (5)
H4	0.7814	0.4959	0.4441	0.078*	0.535 (5)
C3	0.6425 (6)	0.5280 (4)	0.4249 (2)	0.069 (3)	0.535 (5)
H3	0.6199	0.5202	0.4606	0.083*	0.535 (5)
C8	0.8764 (6)	0.5092 (6)	0.3522 (6)	0.078 (2)	0.535 (5)
H8	0.9143	0.4918	0.3831	0.094*	0.535 (5)
O1'	0.4345 (9)	0.5846 (5)	0.3997 (5)	0.090 (3)	0.465 (5)
O2'	0.4298 (7)	0.6000 (5)	0.3094 (5)	0.116 (4)	0.465 (5)
O3'	0.915 (2)	0.4944 (9)	0.3035 (9)	0.098 (2)	0.465 (3)
O1w'	0.4547 (5)	0.8194 (4)	0.2757 (3)	0.061 (2)	0.465 (5)
H1w3	0.4127	0.8226	0.3009	0.073*	0.465 (5)
H1w4	0.4651	0.7706	0.2692	0.073*	0.465 (5)
C1'	0.4733 (6)	0.5834 (4)	0.3539 (4)	0.077 (4)	0.465 (5)
C2'	0.5783 (5)	0.5604 (3)	0.3534 (4)	0.074 (4)	0.465 (5)
C7'	0.6228 (6)	0.5587 (5)	0.3025 (3)	0.094 (5)	0.465 (5)
H7'	0.5876	0.5717	0.2694	0.113*	0.465 (5)
C6'	0.7200 (6)	0.5377 (5)	0.3009 (4)	0.067 (4)	0.465 (5)
H6'	0.7498	0.5365	0.2668	0.081*	0.465 (5)
C5'	0.7725 (5)	0.5183 (6)	0.3502 (5)	0.058 (4)	0.465 (5)
C4'	0.7280 (7)	0.5200 (6)	0.4011 (4)	0.072 (4)	0.465 (5)
H4'	0.7632	0.5071	0.4342	0.086*	0.465 (5)
C3'	0.6308 (6)	0.5411 (5)	0.4028 (3)	0.072 (4)	0.465 (5)
H3'	0.6010	0.5422	0.4368	0.087*	0.465 (5)
C8'	0.8763 (7)	0.4958 (8)	0.3482 (7)	0.078 (2)	0.465
H8'	0.9117	0.4828	0.3812	0.094*	0.465 (5)
C9	0.2289 (4)	0.7213 (3)	0.31636 (18)	0.0580 (12)
C10	0.1726 (3)	0.7564 (3)	0.26685 (17)	0.0531 (11)
C11	0.1190 (4)	0.7085 (3)	0.22931 (19)	0.0687 (14)
H11	0.1211	0.6544	0.2338	0.082*
C12	0.0636 (4)	0.7405 (3)	0.1862 (2)	0.0707 (14)
H12	0.0291	0.7081	0.1610	0.085*
C13	0.0587 (4)	0.8214 (3)	0.17986 (18)	0.0588 (12)
C14	0.1134 (4)	0.8688 (3)	0.2157 (2)	0.0605 (12)
H14	0.1117	0.9229	0.2107	0.073*
C15	0.1708 (3)	0.8370 (3)	0.25929 (18)	0.0578 (12)
H15	0.2079	0.8695	0.2833	0.069*
C16	−0.0066 (4)	0.8548 (4)	0.1356 (2)	0.0796 (16)
H16	−0.0032	0.9087	0.1303	0.096*
C17	0.2429 (3)	0.4136 (3)	0.38937 (17)	0.0514 (11)
C18	0.3076 (4)	0.3910 (3)	0.4323 (2)	0.0693 (14)
H18	0.3472	0.4272	0.4516	0.083*
C19	0.3107 (5)	0.3118 (4)	0.4455 (3)	0.094 (2)
H19	0.3533	0.2945	0.4743	0.113*
C20	0.2518 (5)	0.2577 (4)	0.4165 (3)	0.096 (2)
H20	0.2562	0.2050	0.4264	0.115*
C21	0.1878 (4)	0.2798 (3)	0.3739 (3)	0.0748 (15)
H21	0.1486	0.2435	0.3546	0.090*
C22	0.1838 (4)	0.3586 (3)	0.36096 (19)	0.0569 (11)
C23	0.1566 (4)	0.4757 (3)	0.3263 (2)	0.0722 (15)
H23	0.1299	0.5156	0.3038	0.087*
C24	0.1479 (3)	0.6321 (3)	0.47185 (17)	0.0517 (11)
C25	0.0638 (4)	0.6154 (3)	0.4404 (2)	0.0715 (14)
H25	0.0656	0.5964	0.4039	0.086*
C26	−0.0223 (4)	0.6278 (4)	0.4648 (2)	0.0824 (16)
H26	−0.0801	0.6174	0.4443	0.099*
C27	−0.0258 (4)	0.6556 (4)	0.5192 (2)	0.0814 (16)
H27	−0.0858	0.6615	0.5347	0.098*
C28	0.0567 (4)	0.6746 (3)	0.5511 (2)	0.0720 (15)
H28	0.0541	0.6948	0.5872	0.086*
C29	0.1443 (4)	0.6621 (3)	0.52625 (17)	0.0541 (11)
C30	0.2954 (4)	0.6502 (2)	0.50375 (18)	0.0559 (11)
H30	0.3628	0.6517	0.5067	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0559 (4)	0.0557 (3)	0.0447 (3)	0.0063 (2)	−0.0098 (2)	−0.0017 (2)
N1	0.054 (2)	0.061 (2)	0.050 (2)	0.0063 (18)	−0.0054 (17)	−0.0018 (18)
N2	0.072 (3)	0.069 (3)	0.073 (3)	−0.005 (2)	−0.024 (2)	−0.014 (2)
N3	0.053 (2)	0.054 (2)	0.048 (2)	0.0027 (17)	−0.0162 (16)	0.0006 (17)
N4	0.080 (3)	0.059 (2)	0.0417 (19)	−0.002 (2)	−0.0088 (19)	−0.0067 (18)
O4	0.077 (2)	0.061 (2)	0.0581 (19)	0.0088 (17)	−0.0127 (16)	0.0081 (16)
O5	0.095 (3)	0.079 (2)	0.0533 (19)	0.006 (2)	−0.0263 (18)	−0.0135 (18)
O6	0.092 (3)	0.144 (4)	0.075 (3)	0.020 (3)	−0.029 (2)	0.024 (3)
O1	0.071 (5)	0.081 (5)	0.085 (5)	0.008 (4)	0.012 (4)	0.010 (4)
O2	0.102 (6)	0.109 (5)	0.102 (6)	0.021 (4)	0.035 (5)	0.014 (5)
O3	0.077 (3)	0.112 (6)	0.103 (4)	0.014 (5)	0.003 (3)	−0.003 (4)
O1w	0.129 (7)	0.136 (7)	0.161 (7)	−0.003 (6)	0.038 (6)	0.018 (6)
C1	0.090 (8)	0.053 (5)	0.073 (7)	0.003 (5)	0.015 (6)	−0.004 (5)
C2	0.060 (6)	0.062 (5)	0.058 (6)	−0.003 (5)	−0.014 (5)	−0.020 (5)
C7	0.045 (5)	0.044 (4)	0.068 (6)	−0.006 (4)	−0.029 (5)	−0.009 (4)
C6	0.058 (6)	0.047 (5)	0.045 (5)	−0.002 (4)	−0.007 (4)	−0.014 (4)
C5	0.048 (7)	0.054 (6)	0.073 (6)	−0.006 (5)	−0.017 (5)	−0.005 (5)
C4	0.065 (6)	0.067 (6)	0.061 (5)	−0.010 (5)	−0.016 (5)	0.003 (5)
C3	0.073 (7)	0.071 (6)	0.063 (6)	0.002 (5)	−0.002 (5)	−0.002 (5)
C8	0.070 (4)	0.075 (4)	0.089 (4)	0.004 (3)	−0.009 (3)	0.007 (3)
O1'	0.093 (7)	0.091 (6)	0.089 (7)	−0.002 (5)	0.015 (6)	−0.007 (5)
O2'	0.078 (6)	0.163 (8)	0.104 (7)	0.030 (5)	−0.014 (5)	−0.027 (6)
O3'	0.077 (3)	0.112 (6)	0.103 (4)	0.014 (5)	0.003 (3)	−0.003 (4)
O1w'	0.055 (4)	0.058 (4)	0.069 (4)	−0.008 (3)	0.000 (3)	0.000 (3)
C1'	0.075 (8)	0.079 (7)	0.075 (7)	0.028 (6)	−0.003 (6)	−0.014 (6)
C2'	0.065 (7)	0.069 (7)	0.088 (9)	0.011 (6)	0.000 (7)	−0.006 (6)
C7'	0.087 (8)	0.108 (8)	0.086 (8)	0.014 (7)	−0.002 (7)	−0.007 (7)
C6'	0.064 (7)	0.072 (7)	0.065 (7)	0.007 (5)	−0.002 (5)	−0.014 (6)
C5'	0.052 (8)	0.058 (7)	0.063 (6)	−0.003 (6)	−0.011 (5)	−0.001 (6)
C4'	0.068 (8)	0.069 (7)	0.075 (7)	−0.006 (6)	−0.023 (6)	0.009 (6)
C3'	0.069 (8)	0.077 (7)	0.071 (7)	−0.026 (6)	0.012 (6)	−0.003 (6)
C8'	0.070 (4)	0.075 (4)	0.089 (4)	0.004 (3)	−0.009 (3)	0.007 (3)
C9	0.064 (3)	0.065 (3)	0.044 (2)	0.015 (2)	−0.006 (2)	−0.006 (2)
C10	0.060 (3)	0.056 (3)	0.043 (2)	0.013 (2)	−0.003 (2)	0.000 (2)
C11	0.091 (4)	0.056 (3)	0.056 (3)	0.013 (3)	−0.023 (3)	−0.005 (2)
C12	0.082 (4)	0.077 (3)	0.051 (3)	0.010 (3)	−0.023 (2)	−0.005 (3)
C13	0.056 (3)	0.076 (3)	0.045 (2)	0.017 (2)	0.003 (2)	0.012 (2)
C14	0.058 (3)	0.063 (3)	0.061 (3)	0.009 (2)	0.004 (2)	0.014 (2)
C15	0.057 (3)	0.065 (3)	0.050 (2)	0.000 (2)	0.000 (2)	0.004 (2)
C16	0.070 (4)	0.105 (5)	0.063 (3)	0.023 (3)	−0.005 (3)	0.022 (3)
C17	0.055 (3)	0.058 (3)	0.042 (2)	0.012 (2)	0.0107 (19)	0.000 (2)
C18	0.075 (4)	0.076 (3)	0.057 (3)	0.003 (3)	−0.001 (3)	0.008 (3)
C19	0.098 (5)	0.096 (5)	0.089 (4)	0.014 (4)	−0.005 (4)	0.036 (4)
C20	0.099 (5)	0.072 (4)	0.118 (5)	0.004 (4)	0.024 (4)	0.029 (4)
C21	0.075 (4)	0.064 (3)	0.087 (4)	−0.007 (3)	0.023 (3)	−0.005 (3)
C22	0.058 (3)	0.060 (3)	0.053 (3)	−0.002 (2)	0.010 (2)	−0.009 (2)
C23	0.085 (4)	0.062 (3)	0.066 (3)	0.004 (3)	−0.030 (3)	−0.005 (3)
C24	0.053 (3)	0.054 (3)	0.047 (2)	0.003 (2)	−0.009 (2)	0.001 (2)
C25	0.059 (3)	0.092 (4)	0.062 (3)	0.001 (3)	−0.006 (3)	−0.018 (3)
C26	0.058 (4)	0.108 (4)	0.081 (4)	0.000 (3)	−0.006 (3)	−0.012 (3)
C27	0.072 (4)	0.105 (5)	0.068 (3)	0.003 (3)	0.015 (3)	−0.003 (3)
C28	0.086 (4)	0.081 (4)	0.048 (3)	0.011 (3)	0.006 (3)	0.001 (3)
C29	0.064 (3)	0.056 (3)	0.041 (2)	0.000 (2)	−0.004 (2)	−0.001 (2)
C30	0.067 (3)	0.050 (2)	0.050 (2)	−0.002 (2)	−0.014 (2)	0.002 (2)

Geometric parameters (Å, º)

Zn1—O1	1.919 (9)	C7'—H7'	0.9300
Zn1—O4	1.961 (3)	C6'—C5'	1.3900
Zn1—N3	2.006 (4)	C6'—H6'	0.9300
Zn1—O1'	2.020 (13)	C5'—C4'	1.3900
Zn1—N1	2.038 (4)	C5'—C8'	1.485 (6)
N1—C23	1.316 (6)	C4'—C3'	1.3900
N1—C17	1.387 (5)	C4'—H4'	0.9300
N2—C23	1.321 (6)	C3'—H3'	0.9300
N2—C22	1.372 (6)	C8'—H8'	0.9300
N2—H2n	0.8600	C9—C10	1.504 (6)
N3—C30	1.318 (5)	C10—C15	1.386 (6)
N3—C24	1.397 (6)	C10—C11	1.395 (6)
N4—C30	1.338 (6)	C11—C12	1.362 (6)
N4—C29	1.370 (6)	C11—H11	0.9300
N4—H4n	0.8600	C12—C13	1.389 (7)
O4—C9	1.276 (6)	C12—H12	0.9300
O5—C9	1.232 (6)	C13—C14	1.374 (7)
O6—C16	1.190 (7)	C13—C16	1.468 (7)
O1—C1	1.237 (8)	C14—C15	1.385 (6)
O2—C1	1.239 (8)	C14—H14	0.9300
O3—C8	1.209 (8)	C15—H15	0.9300
O1w—H1w1	0.842	C16—H16	0.9300
O1w—H1w2	0.864	C17—C18	1.379 (7)
C1—C2	1.504 (6)	C17—C22	1.396 (6)
C2—C7	1.3900	C18—C19	1.387 (7)
C2—C3	1.3900	C18—H18	0.9300
C7—C6	1.3900	C19—C20	1.389 (9)
C7—H7	0.9300	C19—H19	0.9300
C6—C5	1.3900	C20—C21	1.364 (8)
C6—H6	0.9300	C20—H20	0.9300
C5—C4	1.3900	C21—C22	1.378 (7)
C5—C8	1.481 (6)	C21—H21	0.9300
C4—C3	1.3900	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.379 (6)
C3—H3	0.9300	C24—C29	1.398 (6)
C8—H8	0.9300	C25—C26	1.366 (8)
O1'—C1'	1.241 (9)	C25—H25	0.9300
O2'—C1'	1.226 (9)	C26—C27	1.384 (7)
O3'—C8'	1.218 (9)	C26—H26	0.9300
O1w'—H1w3	0.86	C27—C28	1.375 (8)
O1w'—H1w4	0.86	C27—H27	0.9300
C1'—C2'	1.500 (6)	C28—C29	1.389 (7)
C2'—C7'	1.3900	C28—H28	0.9300
C2'—C3'	1.3900	C30—H30	0.9300
C7'—C6'	1.3900
O1—Zn1—O4	102.9 (3)	C4'—C3'—C2'	120.0
O1—Zn1—N3	129.5 (3)	C4'—C3'—H3'	120.0
O4—Zn1—N3	108.97 (14)	C2'—C3'—H3'	120.0
O4—Zn1—O1'	131.0 (3)	O3'—C8'—C5'	119.9 (18)
N3—Zn1—O1'	101.2 (3)	O3'—C8'—H8'	120.0
O1—Zn1—N1	109.6 (2)	C5'—C8'—H8'	120.0
O4—Zn1—N1	94.03 (14)	O5—C9—O4	124.7 (4)
N3—Zn1—N1	106.12 (15)	O5—C9—C10	120.1 (4)
O1'—Zn1—N1	113.7 (3)	O4—C9—C10	115.2 (4)
O1—Zn1—C1	26.9 (2)	C15—C10—C11	119.4 (4)
O4—Zn1—C1	129.3 (2)	C15—C10—C9	120.1 (4)
N3—Zn1—C1	107.7 (2)	C11—C10—C9	120.4 (4)
N1—Zn1—C1	107.95 (15)	C12—C11—C10	120.5 (5)
C23—N1—C17	105.1 (4)	C12—C11—H11	119.7
C23—N1—Zn1	124.6 (3)	C10—C11—H11	119.7
C17—N1—Zn1	130.2 (3)	C11—C12—C13	120.1 (5)
C23—N2—C22	108.6 (4)	C11—C12—H12	119.9
C23—N2—H2n	125.7	C13—C12—H12	119.9
C22—N2—H2n	125.7	C14—C13—C12	119.7 (4)
C30—N3—C24	105.2 (4)	C14—C13—C16	121.1 (5)
C30—N3—Zn1	130.2 (3)	C12—C13—C16	119.2 (5)
C24—N3—Zn1	124.5 (3)	C13—C14—C15	120.7 (4)
C30—N4—C29	107.9 (4)	C13—C14—H14	119.6
C30—N4—H4n	126.1	C15—C14—H14	119.6
C29—N4—H4n	126.1	C14—C15—C10	119.5 (4)
C9—O4—Zn1	119.9 (3)	C14—C15—H15	120.3
C1—O1—Zn1	108.4 (7)	C10—C15—H15	120.3
H1w1—O1w—H1w2	107.3	O6—C16—C13	126.8 (6)
O1—C1—O2	121.5 (9)	O6—C16—H16	116.6
O1—C1—C2	119.5 (7)	C13—C16—H16	116.6
O2—C1—C2	118.9 (7)	C18—C17—N1	130.2 (5)
C7—C2—C3	120.0	C18—C17—C22	120.8 (4)
C7—C2—C1	121.6 (4)	N1—C17—C22	109.0 (4)
C3—C2—C1	118.4 (4)	C17—C18—C19	116.9 (5)
C2—C7—C6	120.0	C17—C18—H18	121.6
C2—C7—H7	120.0	C19—C18—H18	121.6
C6—C7—H7	120.0	C18—C19—C20	121.6 (6)
C7—C6—C5	120.0	C18—C19—H19	119.2
C7—C6—H6	120.0	C20—C19—H19	119.2
C5—C6—H6	120.0	C21—C20—C19	121.7 (6)
C6—C5—C4	120.0	C21—C20—H20	119.1
C6—C5—C8	120.9 (5)	C19—C20—H20	119.1
C4—C5—C8	119.1 (5)	C20—C21—C22	117.0 (6)
C3—C4—C5	120.0	C20—C21—H21	121.5
C3—C4—H4	120.0	C22—C21—H21	121.5
C5—C4—H4	120.0	N2—C22—C21	133.3 (5)
C4—C3—C2	120.0	N2—C22—C17	104.6 (4)
C4—C3—H3	120.0	C21—C22—C17	122.1 (5)
C2—C3—H3	120.0	N1—C23—N2	112.6 (4)
O3—C8—C5	127.5 (16)	N1—C23—H23	123.7
O3—C8—H8	116.2	N2—C23—H23	123.7
C5—C8—H8	116.2	C25—C24—N3	130.7 (4)
C1'—O1'—Zn1	107.5 (9)	C25—C24—C29	120.7 (5)
H1w3—O1w'—H1w4	108.2	N3—C24—C29	108.6 (4)
O2'—C1'—O1'	123.0 (11)	C26—C25—C24	117.6 (5)
O2'—C1'—C2'	118.9 (8)	C26—C25—H25	121.2
O1'—C1'—C2'	118.2 (9)	C24—C25—H25	121.2
C7'—C2'—C3'	120.0	C25—C26—C27	121.7 (6)
C7'—C2'—C1'	118.9 (5)	C25—C26—H26	119.2
C3'—C2'—C1'	121.1 (5)	C27—C26—H26	119.2
C6'—C7'—C2'	120.0	C28—C27—C26	122.1 (5)
C6'—C7'—H7'	120.0	C28—C27—H27	118.9
C2'—C7'—H7'	120.0	C26—C27—H27	118.9
C7'—C6'—C5'	120.0	C27—C28—C29	116.2 (5)
C7'—C6'—H6'	120.0	C27—C28—H28	121.9
C5'—C6'—H6'	120.0	C29—C28—H28	121.9
C6'—C5'—C4'	120.0	N4—C29—C28	132.7 (4)
C6'—C5'—C8'	119.8 (5)	N4—C29—C24	105.6 (4)
C4'—C5'—C8'	120.2 (5)	C28—C29—C24	121.7 (5)
C3'—C4'—C5'	120.0	N3—C30—N4	112.7 (4)
C3'—C4'—H4'	120.0	N3—C30—H30	123.6
C5'—C4'—H4'	120.0	N4—C30—H30	123.6
O1—Zn1—N1—C23	−104.9 (5)	O4—C9—C10—C15	169.3 (4)
O4—Zn1—N1—C23	0.3 (4)	O5—C9—C10—C11	172.2 (5)
N3—Zn1—N1—C23	111.4 (4)	O4—C9—C10—C11	−8.4 (7)
O1'—Zn1—N1—C23	−138.3 (5)	C15—C10—C11—C12	−1.4 (8)
C1—Zn1—N1—C23	−133.3 (4)	C9—C10—C11—C12	176.3 (5)
O1—Zn1—N1—C17	71.5 (5)	C10—C11—C12—C13	−1.1 (8)
O4—Zn1—N1—C17	176.7 (4)	C11—C12—C13—C14	2.9 (8)
N3—Zn1—N1—C17	−72.2 (4)	C11—C12—C13—C16	−175.7 (5)
O1'—Zn1—N1—C17	38.1 (5)	C12—C13—C14—C15	−2.2 (7)
C1—Zn1—N1—C17	43.1 (4)	C16—C13—C14—C15	176.5 (4)
O1—Zn1—N3—C30	−3.3 (5)	C13—C14—C15—C10	−0.4 (7)
O4—Zn1—N3—C30	−129.4 (4)	C11—C10—C15—C14	2.1 (7)
O1'—Zn1—N3—C30	11.5 (5)	C9—C10—C15—C14	−175.6 (4)
N1—Zn1—N3—C30	130.5 (4)	C14—C13—C16—O6	−172.6 (6)
C1—Zn1—N3—C30	15.0 (4)	C12—C13—C16—O6	6.1 (9)
O1—Zn1—N3—C24	171.5 (4)	C23—N1—C17—C18	179.7 (5)
O4—Zn1—N3—C24	45.4 (4)	Zn1—N1—C17—C18	2.7 (7)
O1'—Zn1—N3—C24	−173.7 (4)	C23—N1—C17—C22	1.0 (5)
N1—Zn1—N3—C24	−54.8 (3)	Zn1—N1—C17—C22	−176.0 (3)
C1—Zn1—N3—C24	−170.2 (3)	N1—C17—C18—C19	−178.5 (5)
O1—Zn1—O4—C9	−67.1 (4)	C22—C17—C18—C19	0.1 (7)
N3—Zn1—O4—C9	73.1 (4)	C17—C18—C19—C20	0.3 (9)
O1'—Zn1—O4—C9	−51.7 (5)	C18—C19—C20—C21	−0.2 (10)
N1—Zn1—O4—C9	−178.3 (3)	C19—C20—C21—C22	−0.2 (9)
C1—Zn1—O4—C9	−61.1 (4)	C23—N2—C22—C21	−178.5 (5)
O4—Zn1—O1—C1	169.7 (3)	C23—N2—C22—C17	0.7 (5)
N3—Zn1—O1—C1	41.4 (4)	C20—C21—C22—N2	179.7 (5)
O1'—Zn1—O1—C1	12.5 (6)	C20—C21—C22—C17	0.6 (8)
N1—Zn1—O1—C1	−91.2 (3)	C18—C17—C22—N2	−179.9 (4)
Zn1—O1—C1—O2	−7.5 (3)	N1—C17—C22—N2	−1.0 (5)
Zn1—O1—C1—C2	172.5 (3)	C18—C17—C22—C21	−0.6 (7)
O1—C1—C2—C7	−0.03 (7)	N1—C17—C22—C21	178.3 (4)
O2—C1—C2—C7	−179.99 (4)	C17—N1—C23—N2	−0.5 (6)
Zn1—C1—C2—C7	18.3 (8)	Zn1—N1—C23—N2	176.6 (3)
O1—C1—C2—C3	180.00 (4)	C22—N2—C23—N1	−0.1 (6)
O2—C1—C2—C3	0.04 (7)	C30—N3—C24—C25	179.3 (5)
Zn1—C1—C2—C3	−161.7 (8)	Zn1—N3—C24—C25	3.4 (7)
C6—C5—C8—O3	0.04 (9)	C30—N3—C24—C29	0.3 (5)
C4—C5—C8—O3	−179.97 (5)	Zn1—N3—C24—C29	−175.6 (3)
O1—Zn1—O1'—C1'	−6.3 (5)	N3—C24—C25—C26	179.9 (5)
O4—Zn1—O1'—C1'	−36.2 (5)	C29—C24—C25—C26	−1.2 (8)
N3—Zn1—O1'—C1'	−163.9 (3)	C24—C25—C26—C27	−0.5 (9)
N1—Zn1—O1'—C1'	82.7 (4)	C25—C26—C27—C28	2.2 (10)
C1—Zn1—O1'—C1'	43 (3)	C26—C27—C28—C29	−2.0 (9)
Zn1—O1'—C1'—O2'	13.1 (3)	C30—N4—C29—C28	179.2 (5)
Zn1—O1'—C1'—C2'	−166.9 (3)	C30—N4—C29—C24	−0.2 (5)
O2'—C1'—C2'—C7'	−0.03 (7)	C27—C28—C29—N4	−179.1 (5)
O1'—C1'—C2'—C7'	−179.99 (4)	C27—C28—C29—C24	0.3 (7)
O2'—C1'—C2'—C3'	180.00 (4)	C25—C24—C29—N4	−179.1 (4)
O1'—C1'—C2'—C3'	0.04 (7)	N3—C24—C29—N4	0.0 (5)
C1'—C2'—C3'—C4'	179.97 (5)	C25—C24—C29—C28	1.4 (7)
C6'—C5'—C8'—O3'	0.03 (8)	N3—C24—C29—C28	−179.5 (4)
C4'—C5'—C8'—O3'	−179.98 (4)	C24—N3—C30—N4	−0.5 (5)
Zn1—O4—C9—O5	−5.9 (7)	Zn1—N3—C30—N4	175.1 (3)
Zn1—O4—C9—C10	174.8 (3)	C29—N4—C30—N3	0.5 (5)
O5—C9—C10—C15	−10.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1w′^i	0.86	2.12	2.907 (8)	152
N2—H2n···O1w′^ii	0.86	2.17	2.960 (8)	154
N4—H4n···O5^iii	0.86	2.11	2.864 (5)	145
O1w—H1w1···O1	0.84	2.064 (7)	2.87 (1)	159
O1w—H1w2···O5	0.86	1.873 (4)	2.69 (1)	157
O1w′—H1w3···O5	0.86	2.353 (4)	3.112 (8)	148

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