Bis[2-(benzimidazol-2-yl)phenolato]zinc(II)–[2-(benzimidazol-2-­yl)phenolato][2-(benzimidazol-2-yl)-4-bromo­phenolato]zinc(II)–ethanol–water (0.67/0.33/2/0.5)

Tong, Y.-P.

doi:10.1107/S1600536805025328

Bis[2-(benzimidazol-2-yl)phenolato]zinc(II)-[2-(benzimidazol-2-yl)phenolato][2-(benzimidazol-2-yl)-4-bromophenolato]zinc(II)-ethanol-water (0.67/0.33/2/0.5)

In the structure of the title compound, [Zn(C₁₃H₉N₂O)(C₁₃H_8.67Br_0.33N₂O)]·2C₂H₆O·0.5H₂O, the central zinc(II) ion is surrounded by an N₂O₂ environment with a tetrahedral geometry. One of the two deprotonated 2-(benzimidazol-2-yl)phenolate ligands is statistically disordered with 2-(benzimidazol-2-yl)-4-bromophenolate, with an occupancy ratio of 0.67 (2):0.33 (2). Ethanol and water molecules co-crystallize in the orthorhombic system, with the water O atom on a twofold axis. The complex molecules are linked to one another by intermolecular hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025328/br6209sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025328/br6209Isup2.hkl Contains datablock I

CCDC reference: 269152

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.020 Å
Disorder in main residue
R factor = 0.064
wR factor = 0.209
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         20
PLAT432_ALERT_2_B Short Inter X...Y Contact  Br1    ..  C28     ..       3.11 Ang.

Alert level C
CHEMW01_ALERT_1_C  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.99 <> 1.01
            Calculated formula weight =   625.0214
            Formula weight given      =   611.2600
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C27
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C29
PLAT301_ALERT_3_C Main Residue  Disorder .........................       1.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C27    -   C28    ...       1.35 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C29    -   C30    ...       1.34 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.35(3), Rep   1.348(10) ......       3.00 su-Rat
              C27  -C28     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.34(3), Rep   1.335(10) ......       3.00 su-Rat
              C29  -C30     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C52 H35.34 Br0.66 N8 O4 Zn2

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 H30.67 Br0.33 N5 O4.5 Z
            Atom count from _chemical_formula_moiety:C30 H30.67 Br0.33 N4 O4.5 Z
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C30 H30.67 Br0.33 N5 O4.5 Zn1
            Atom count from the _atom_site data:  C30 H30.67 Br0.33 N4 O4.5 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C30 H30.67 Br0.33 N5 O4.5 Zn1
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        240.00    240.00    0.00
           H        245.36    245.36    0.00
           Br         2.64      2.64    0.00
           N         40.00     32.00    8.00
           O         36.00     36.00    0.00
           Zn         8.00      8.00    0.00
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           25.99
           From the CIF: _reflns_number_total               4727
           Count of symmetry unique reflns         2953
           Completeness (_total/calc)            160.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1774
           Fraction of Friedel pairs measured     0.601
           Are heavy atom types Z>Si present        yes

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

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

Computing details top

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: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.

[2-(Benzimidazol-2-yl)phenolato]zinc(II)–[2-(benzimidazol-2- yl)phenolato][2-(benzimidazol-2-yl)-4-bromophenolato]zinc(II)–ethanol–water (0.67/0.33/2/0.5) top

Crystal data top

[Zn(C₁₃H₉N₂O)(C₁₃H_8.67Br_0.33N₂O)]·2C₂H₆O·0.5H₂O	F(000) = 2531
M_r = 611.26	D_x = 1.396 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 1648 reflections
a = 32.459 (3) Å	θ = 2.3–26.1°
b = 9.408 (1) Å	µ = 1.35 mm⁻¹
c = 19.053 (2) Å	T = 293 K
V = 5818.5 (10) Å³	Plate, colorless
Z = 8	0.36 × 0.26 × 0.05 mm

Data collection top

Bruker APEX area-detector diffractometer	4727 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
φ and ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→31
T_min = 0.643, T_max = 0.936	k = −11→10
12802 measured reflections	l = −18→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.209	w = 1/[σ²(F_o²) + (0.1164P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
4727 reflections	Δρ_max = 0.61 e Å⁻³
303 parameters	Δρ_min = −0.54 e Å⁻³
33 restraints	Absolute structure: Flack (1983), 1772 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (3)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.48567 (15)	−0.3818 (4)	0.5435 (3)	0.155 (2)	0.33
Zn1	0.34497 (3)	0.23178 (9)	0.50481 (10)	0.0664 (3)
O1	0.34597 (15)	0.0265 (6)	0.4892 (3)	0.0675 (17)
O2	0.34726 (18)	0.3489 (8)	0.4225 (4)	0.084 (2)
N1	0.3903 (2)	0.2287 (7)	0.5722 (4)	0.065 (2)
N2	0.4408 (2)	0.1415 (9)	0.6351 (5)	0.079 (2)
H2A	0.4590	0.0826	0.6503	0.094*
N3	0.2906 (2)	0.2948 (8)	0.5336 (4)	0.067 (2)
N4	0.2277 (2)	0.3849 (7)	0.5199 (4)	0.0598 (19)
H4A	0.2077	0.4336	0.5025	0.072*
C1	0.37820 (16)	−0.0599 (5)	0.5044 (4)	0.070 (2)
C2	0.37687 (18)	−0.1931 (6)	0.4729 (3)	0.081 (3)
H2B	0.3551	−0.2166	0.4433	0.097*
C3	0.4080 (2)	−0.2911 (5)	0.4856 (4)	0.099 (4)
H3A	0.4071	−0.3802	0.4645	0.119*
C4	0.4405 (2)	−0.2560 (7)	0.5299 (5)	0.101 (4)
H4	0.4614	−0.3216	0.5384	0.122*	0.67
C5	0.44185 (17)	−0.1229 (7)	0.5614 (4)	0.086 (3)
H5A	0.4636	−0.0994	0.5910	0.103*
C6	0.41069 (17)	−0.0248 (5)	0.5487 (4)	0.068 (2)
C7	0.4138 (2)	0.1143 (9)	0.5840 (5)	0.059 (2)
C8	0.4032 (2)	0.3315 (7)	0.6199 (3)	0.073 (3)
C9	0.3888 (2)	0.4680 (7)	0.6332 (4)	0.098 (3)
H9A	0.3673	0.5050	0.6067	0.117*
C10	0.4066 (2)	0.5492 (7)	0.6861 (5)	0.103 (4)
H10A	0.3970	0.6406	0.6950	0.123*
C11	0.4388 (2)	0.4939 (9)	0.7256 (4)	0.112 (4)
H11A	0.4507	0.5482	0.7610	0.135*
C12	0.4532 (2)	0.3574 (9)	0.7124 (4)	0.120 (5)
H12A	0.4748	0.3204	0.7388	0.144*
C13	0.4354 (2)	0.2762 (6)	0.6595 (4)	0.084 (3)
C14	0.31875 (16)	0.4465 (6)	0.4021 (3)	0.064 (2)
C15	0.33007 (16)	0.5283 (7)	0.3445 (3)	0.070 (2)
H15A	0.3558	0.5160	0.3240	0.083*
C16	0.3029 (2)	0.6285 (7)	0.3175 (3)	0.087 (3)
H16A	0.3105	0.6832	0.2790	0.104*
C17	0.2644 (2)	0.6469 (6)	0.3481 (4)	0.084 (3)
H17A	0.2462	0.7140	0.3301	0.101*
C18	0.25307 (15)	0.5651 (7)	0.4057 (3)	0.072 (2)
H18A	0.2273	0.5774	0.4262	0.086*
C19	0.28025 (17)	0.4649 (6)	0.4327 (3)	0.062 (2)
C20	0.2666 (2)	0.3800 (8)	0.4958 (5)	0.059 (2)
C21	0.26540 (15)	0.2432 (6)	0.5853 (3)	0.059 (2)
C22	0.27404 (16)	0.1525 (7)	0.6410 (3)	0.085 (3)
H22A	0.3004	0.1157	0.6465	0.102*
C23	0.2432 (2)	0.1169 (7)	0.6885 (3)	0.085 (3)
H23A	0.2490	0.0562	0.7258	0.101*
C24	0.20378 (19)	0.1720 (8)	0.6803 (3)	0.092 (3)
H24A	0.1832	0.1481	0.7121	0.110*
C25	0.19514 (14)	0.2626 (7)	0.6247 (4)	0.082 (3)
H25A	0.1687	0.2995	0.6192	0.099*
C26	0.22595 (17)	0.2983 (6)	0.5772 (3)	0.059 (2)
O1W	0.5000	0.0000	0.7192 (5)	0.082 (3)
H1W	0.515 (2)	0.053 (8)	0.744 (2)	0.098*
O3	0.4645 (4)	0.8148 (12)	0.8117 (6)	0.156 (4)
H3O	0.4393	0.8147	0.8082	0.233*
O4	0.3802 (4)	0.8127 (13)	0.8128 (6)	0.171 (5)
H4O	0.3696	0.7591	0.8415	0.257*
C27	0.4754 (9)	0.822 (2)	0.8810 (9)	0.260 (7)
H27A	0.5049	0.8342	0.8856	0.312*
H27B	0.4617	0.9010	0.9036	0.312*
C28	0.4636 (8)	0.698 (2)	0.9106 (10)	0.260 (7)
H28A	0.4690	0.7012	0.9601	0.390*
H28B	0.4787	0.6211	0.8899	0.390*
H28C	0.4346	0.6840	0.9030	0.390*
C29	0.3574 (7)	0.935 (2)	0.8083 (15)	0.260 (7)
H29A	0.3295	0.9139	0.7933	0.312*
H29B	0.3562	0.9818	0.8537	0.312*
C30	0.3758 (7)	1.020 (2)	0.7616 (15)	0.260 (7)
H30A	0.3613	1.1084	0.7588	0.390*
H30B	0.3757	0.9746	0.7164	0.390*
H30C	0.4038	1.0370	0.7759	0.390*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.150 (4)	0.118 (3)	0.199 (5)	0.079 (3)	−0.073 (4)	−0.061 (3)
Zn1	0.0567 (5)	0.0719 (6)	0.0707 (6)	0.0027 (4)	−0.0004 (6)	0.0004 (8)
O1	0.054 (3)	0.077 (3)	0.071 (5)	−0.003 (3)	−0.008 (3)	0.007 (3)
O2	0.062 (4)	0.101 (5)	0.091 (5)	0.016 (3)	0.022 (4)	0.019 (4)
N1	0.064 (4)	0.053 (4)	0.079 (5)	−0.003 (4)	0.006 (4)	−0.011 (4)
N2	0.061 (5)	0.075 (5)	0.101 (7)	0.018 (4)	−0.021 (5)	−0.017 (5)
N3	0.070 (5)	0.073 (5)	0.056 (4)	−0.001 (4)	−0.006 (4)	0.002 (4)
N4	0.052 (4)	0.072 (4)	0.055 (5)	0.010 (3)	0.002 (3)	−0.004 (4)
C1	0.073 (5)	0.071 (5)	0.068 (5)	−0.003 (4)	0.002 (6)	−0.010 (7)
C2	0.083 (7)	0.068 (6)	0.091 (7)	−0.007 (5)	0.002 (5)	−0.022 (6)
C3	0.113 (9)	0.068 (6)	0.116 (13)	0.028 (6)	0.004 (7)	−0.016 (7)
C4	0.083 (7)	0.107 (9)	0.115 (11)	0.027 (6)	−0.021 (7)	−0.017 (8)
C5	0.072 (6)	0.082 (7)	0.104 (9)	0.014 (5)	−0.003 (5)	−0.017 (7)
C6	0.048 (5)	0.080 (6)	0.076 (6)	−0.001 (4)	0.002 (4)	−0.001 (5)
C7	0.050 (5)	0.055 (5)	0.072 (6)	0.001 (4)	−0.003 (4)	−0.017 (5)
C8	0.067 (6)	0.064 (6)	0.089 (7)	−0.005 (5)	0.003 (5)	−0.018 (6)
C9	0.085 (7)	0.075 (7)	0.134 (11)	0.001 (6)	−0.015 (7)	−0.001 (8)
C10	0.095 (8)	0.091 (8)	0.122 (10)	0.002 (6)	−0.032 (7)	−0.046 (8)
C11	0.096 (8)	0.115 (9)	0.125 (11)	0.000 (8)	−0.006 (7)	−0.068 (9)
C12	0.079 (8)	0.123 (10)	0.157 (13)	−0.014 (7)	−0.032 (7)	−0.062 (10)
C13	0.061 (6)	0.098 (8)	0.093 (8)	−0.012 (6)	−0.004 (5)	−0.018 (7)
C14	0.064 (6)	0.063 (5)	0.066 (6)	−0.003 (4)	0.000 (5)	−0.002 (5)
C15	0.078 (6)	0.076 (6)	0.055 (6)	−0.002 (5)	0.017 (5)	−0.002 (5)
C16	0.136 (10)	0.067 (7)	0.058 (6)	−0.019 (6)	0.013 (6)	−0.002 (5)
C17	0.103 (8)	0.081 (7)	0.068 (7)	0.015 (6)	0.005 (6)	0.020 (6)
C18	0.077 (6)	0.068 (6)	0.070 (6)	0.010 (5)	0.004 (5)	−0.002 (5)
C19	0.058 (5)	0.070 (6)	0.059 (5)	−0.010 (4)	0.006 (4)	−0.003 (5)
C20	0.063 (5)	0.057 (4)	0.058 (6)	0.003 (4)	0.007 (5)	0.000 (5)
C21	0.053 (5)	0.053 (5)	0.069 (6)	−0.002 (4)	−0.001 (4)	0.011 (4)
C22	0.076 (7)	0.092 (7)	0.087 (8)	−0.010 (6)	0.006 (6)	−0.012 (7)
C23	0.084 (7)	0.110 (9)	0.060 (7)	0.012 (6)	0.012 (6)	0.023 (6)
C24	0.095 (9)	0.108 (9)	0.072 (7)	−0.012 (7)	0.012 (6)	0.016 (7)
C25	0.078 (7)	0.088 (7)	0.080 (8)	0.005 (5)	0.014 (5)	0.009 (6)
C26	0.056 (5)	0.056 (5)	0.064 (6)	−0.001 (4)	0.011 (4)	0.001 (5)
O1W	0.063 (6)	0.098 (8)	0.085 (7)	−0.011 (5)	0.000	0.000
O3	0.167 (9)	0.152 (8)	0.147 (10)	−0.050 (8)	0.060 (7)	−0.013 (8)
O4	0.203 (12)	0.146 (9)	0.166 (11)	−0.042 (8)	0.082 (9)	0.020 (8)
C27	0.281 (15)	0.259 (15)	0.240 (16)	−0.050 (13)	0.010 (13)	0.076 (13)
C28	0.281 (15)	0.259 (15)	0.240 (16)	−0.050 (13)	0.010 (13)	0.076 (13)
C29	0.281 (15)	0.259 (15)	0.240 (16)	−0.050 (13)	0.010 (13)	0.076 (13)
C30	0.281 (15)	0.259 (15)	0.240 (16)	−0.050 (13)	0.010 (13)	0.076 (13)

Geometric parameters (Å, º) top

Br1—C4	1.901 (6)	C14—C15	1.3900
Zn1—O2	1.917 (7)	C14—C19	1.3900
Zn1—N3	1.942 (8)	C15—C16	1.3900
Zn1—N1	1.953 (8)	C15—H15A	0.9300
Zn1—O1	1.954 (6)	C16—C17	1.3900
O1—C1	1.357 (7)	C16—H16A	0.9300
O2—C14	1.360 (8)	C17—C18	1.3900
N1—C7	1.338 (10)	C17—H17A	0.9300
N1—C8	1.392 (9)	C18—C19	1.3900
N2—C7	1.335 (11)	C18—H18A	0.9300
N2—C13	1.361 (9)	C19—C20	1.509 (10)
N2—H2A	0.8600	C21—C22	1.3900
N3—C20	1.329 (11)	C21—C26	1.3900
N3—C21	1.370 (9)	C22—C23	1.3900
N4—C20	1.344 (10)	C22—H22A	0.9300
N4—C26	1.364 (7)	C23—C24	1.3900
N4—H4A	0.8600	C23—H23A	0.9300
C1—C2	1.3900	C24—C25	1.3900
C1—C6	1.3900	C24—H24A	0.9300
C2—C3	1.3900	C25—C26	1.3900
C2—H2B	0.9300	C25—H25A	0.9300
C3—C4	1.3900	O1W—H1W	0.84 (2)
C3—H3A	0.9300	O3—C27	1.368 (10)
C4—C5	1.3900	O3—H3O	0.8200
C4—H4	0.9300	O4—C29	1.372 (10)
C5—C6	1.3900	O4—H4O	0.8200
C5—H5A	0.9300	C27—C28	1.348 (10)
C6—C7	1.475 (9)	C27—H27A	0.9700
C8—C9	1.3900	C27—H27B	0.9700
C8—C13	1.3900	C28—H28A	0.9600
C9—C10	1.3900	C28—H28B	0.9600
C9—H9A	0.9300	C28—H28C	0.9600
C10—C11	1.3900	C29—C30	1.335 (10)
C10—H10A	0.9300	C29—H29A	0.9700
C11—C12	1.3900	C29—H29B	0.9700
C11—H11A	0.9300	C30—H30A	0.9600
C12—C13	1.3900	C30—H30B	0.9600
C12—H12A	0.9300	C30—H30C	0.9600

O2—Zn1—N3	95.2 (3)	C15—C14—C19	120.0
O2—Zn1—N1	121.1 (3)	C16—C15—C14	120.0
N3—Zn1—N1	120.3 (3)	C16—C15—H15A	120.0
O2—Zn1—O1	116.3 (3)	C14—C15—H15A	120.0
N3—Zn1—O1	111.1 (3)	C17—C16—C15	120.0
N1—Zn1—O1	94.2 (3)	C17—C16—H16A	120.0
C1—O1—Zn1	125.0 (4)	C15—C16—H16A	120.0
C14—O2—Zn1	126.5 (5)	C16—C17—C18	120.0
C7—N1—C8	106.1 (7)	C16—C17—H17A	120.0
C7—N1—Zn1	123.5 (6)	C18—C17—H17A	120.0
C8—N1—Zn1	130.2 (5)	C19—C18—C17	120.0
C7—N2—C13	110.0 (7)	C19—C18—H18A	120.0
C7—N2—H2A	125.0	C17—C18—H18A	120.0
C13—N2—H2A	125.0	C18—C19—C14	120.0
C20—N3—C21	104.7 (7)	C18—C19—C20	117.8 (5)
C20—N3—Zn1	124.3 (6)	C14—C19—C20	122.2 (5)
C21—N3—Zn1	129.6 (5)	N3—C20—N4	112.7 (8)
C20—N4—C26	107.0 (6)	N3—C20—C19	125.3 (7)
C20—N4—H4A	126.5	N4—C20—C19	122.0 (7)
C26—N4—H4A	126.5	N3—C21—C22	130.3 (5)
O1—C1—C2	115.1 (5)	N3—C21—C26	109.7 (5)
O1—C1—C6	124.9 (5)	C22—C21—C26	120.0
C2—C1—C6	120.0	C21—C22—C23	120.0
C1—C2—C3	120.0	C21—C22—H22A	120.0
C1—C2—H2B	120.0	C23—C22—H22A	120.0
C3—C2—H2B	120.0	C22—C23—C24	120.0
C4—C3—C2	120.0	C22—C23—H23A	120.0
C4—C3—H3A	120.0	C24—C23—H23A	120.0
C2—C3—H3A	120.0	C23—C24—C25	120.0
C3—C4—C5	120.0	C23—C24—H24A	120.0
C3—C4—Br1	121.3 (4)	C25—C24—H24A	120.0
C5—C4—Br1	118.6 (4)	C26—C25—C24	120.0
C3—C4—H4	120.0	C26—C25—H25A	120.0
C5—C4—H4	120.0	C24—C25—H25A	120.0
C4—C5—C6	120.0	N4—C26—C25	134.1 (5)
C4—C5—H5A	120.0	N4—C26—C21	105.9 (5)
C6—C5—H5A	120.0	C25—C26—C21	120.0
C5—C6—C1	120.0	C27—O3—H3O	109.5
C5—C6—C7	117.3 (5)	C29—O4—H4O	109.5
C1—C6—C7	122.7 (5)	C28—C27—O3	107.0 (10)
N2—C7—N1	110.1 (7)	C28—C27—H27A	110.3
N2—C7—C6	123.2 (7)	O3—C27—H27A	110.3
N1—C7—C6	126.7 (8)	C28—C27—H27B	110.3
C9—C8—C13	120.0	O3—C27—H27B	110.3
C9—C8—N1	131.3 (5)	H27A—C27—H27B	108.6
C13—C8—N1	108.7 (5)	C27—C28—H28A	109.5
C10—C9—C8	120.0	C27—C28—H28B	109.5
C10—C9—H9A	120.0	H28A—C28—H28B	109.5
C8—C9—H9A	120.0	C27—C28—H28C	109.5
C9—C10—C11	120.0	H28A—C28—H28C	109.5
C9—C10—H10A	120.0	H28B—C28—H28C	109.5
C11—C10—H10A	120.0	C30—C29—O4	107.5 (10)
C12—C11—C10	120.0	C30—C29—H29A	110.2
C12—C11—H11A	120.0	O4—C29—H29A	110.2
C10—C11—H11A	120.0	C30—C29—H29B	110.2
C11—C12—C13	120.0	O4—C29—H29B	110.2
C11—C12—H12A	120.0	H29A—C29—H29B	108.5
C13—C12—H12A	120.0	C29—C30—H30A	109.5
N2—C13—C12	134.8 (6)	C29—C30—H30B	109.5
N2—C13—C8	105.1 (6)	H30A—C30—H30B	109.5
C12—C13—C8	120.0	C29—C30—H30C	109.5
O2—C14—C15	114.8 (5)	H30A—C30—H30C	109.5
O2—C14—C19	125.1 (5)	H30B—C30—H30C	109.5

O2—Zn1—O1—C1	108.7 (6)	C9—C10—C11—C12	0.0
N3—Zn1—O1—C1	−143.9 (6)	C10—C11—C12—C13	0.0
N1—Zn1—O1—C1	−19.1 (6)	C7—N2—C13—C12	177.3 (7)
N3—Zn1—O2—C14	4.4 (7)	C7—N2—C13—C8	−0.3 (9)
N1—Zn1—O2—C14	−125.9 (6)	C11—C12—C13—N2	−177.3 (10)
O1—Zn1—O2—C14	121.0 (6)	C11—C12—C13—C8	0.0
O2—Zn1—N1—C7	−114.2 (7)	C9—C8—C13—N2	178.0 (7)
N3—Zn1—N1—C7	127.4 (7)	N1—C8—C13—N2	−0.5 (7)
O1—Zn1—N1—C7	10.0 (7)	C9—C8—C13—C12	0.0
O2—Zn1—N1—C8	71.3 (8)	N1—C8—C13—C12	−178.5 (6)
N3—Zn1—N1—C8	−47.1 (8)	Zn1—O2—C14—C15	173.1 (4)
O1—Zn1—N1—C8	−164.5 (7)	Zn1—O2—C14—C19	−9.0 (9)
O2—Zn1—N3—C20	6.2 (7)	O2—C14—C15—C16	178.0 (6)
N1—Zn1—N3—C20	137.0 (7)	C19—C14—C15—C16	0.0
O1—Zn1—N3—C20	−114.6 (7)	C14—C15—C16—C17	0.0
O2—Zn1—N3—C21	171.0 (7)	C15—C16—C17—C18	0.0
N1—Zn1—N3—C21	−58.2 (8)	C16—C17—C18—C19	0.0
O1—Zn1—N3—C21	50.2 (7)	C17—C18—C19—C14	0.0
Zn1—O1—C1—C2	−163.8 (4)	C17—C18—C19—C20	179.4 (6)
Zn1—O1—C1—C6	17.1 (8)	O2—C14—C19—C18	−177.8 (7)
O1—C1—C2—C3	−179.1 (7)	C15—C14—C19—C18	0.0
C6—C1—C2—C3	0.0	O2—C14—C19—C20	2.9 (7)
C1—C2—C3—C4	0.0	C15—C14—C19—C20	−179.4 (6)
C2—C3—C4—C5	0.0	C21—N3—C20—N4	−0.5 (9)
C2—C3—C4—Br1	−175.5 (7)	Zn1—N3—C20—N4	167.4 (6)
C3—C4—C5—C6	0.0	C21—N3—C20—C19	179.0 (7)
Br1—C4—C5—C6	175.6 (7)	Zn1—N3—C20—C19	−13.1 (12)
C4—C5—C6—C1	0.0	C26—N4—C20—N3	0.2 (9)
C4—C5—C6—C7	179.7 (7)	C26—N4—C20—C19	−179.3 (6)
O1—C1—C6—C5	179.0 (8)	C18—C19—C20—N3	−170.3 (7)
C2—C1—C6—C5	0.0	C14—C19—C20—N3	9.1 (11)
O1—C1—C6—C7	−0.7 (8)	C18—C19—C20—N4	9.1 (10)
C2—C1—C6—C7	−179.7 (7)	C14—C19—C20—N4	−171.5 (6)
C13—N2—C7—N1	1.0 (11)	C20—N3—C21—C22	−178.1 (6)
C13—N2—C7—C6	−177.5 (8)	Zn1—N3—C21—C22	14.8 (10)
C8—N1—C7—N2	−1.3 (10)	C20—N3—C21—C26	0.6 (7)
Zn1—N1—C7—N2	−176.9 (6)	Zn1—N3—C21—C26	−166.5 (5)
C8—N1—C7—C6	177.1 (8)	N3—C21—C22—C23	178.6 (8)
Zn1—N1—C7—C6	1.5 (13)	C26—C21—C22—C23	0.0
C5—C6—C7—N2	−11.0 (11)	C21—C22—C23—C24	0.0
C1—C6—C7—N2	168.7 (7)	C22—C23—C24—C25	0.0
C5—C6—C7—N1	170.8 (8)	C23—C24—C25—C26	0.0
C1—C6—C7—N1	−9.5 (12)	C20—N4—C26—C25	178.2 (6)
C7—N1—C8—C9	−177.2 (7)	C20—N4—C26—C21	0.1 (7)
Zn1—N1—C8—C9	−2.0 (11)	C24—C25—C26—N4	−177.8 (8)
C7—N1—C8—C13	1.1 (8)	C24—C25—C26—C21	0.0
Zn1—N1—C8—C13	176.3 (5)	N3—C21—C26—N4	−0.5 (6)
C13—C8—C9—C10	0.0	C22—C21—C26—N4	178.4 (6)
N1—C8—C9—C10	178.2 (8)	N3—C21—C26—C25	−178.8 (6)
C8—C9—C10—C11	0.0	C22—C21—C26—C25	0.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3ⁱ	0.84 (2)	1.91 (3)	2.733 (11)	165 (8)
O4—H4O···O2ⁱⁱ	0.82	1.98	2.797 (12)	171
O3—H3O···O4	0.82	1.92	2.738 (16)	173
N2—H2A···O1W	0.86	2.02	2.833 (9)	157
N4—H4A···O1ⁱⁱⁱ	0.86	1.97	2.799 (8)	163

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

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Bis[2-(benzimidazol-2-yl)phenolato]zinc(II)-[2-(benzimidazol-2-­yl)phenolato][2-(benzimidazol-2-yl)-4-bromo­phenolato]zinc(II)-ethanol-water (0.67/0.33/2/0.5)

Supporting information

Key indicators

checkCIF/PLATON results

Bis[2-(benzimidazol-2-yl)phenolato]zinc(II)-[2-(benzimidazol-2-yl)phenolato][2-(benzimidazol-2-yl)-4-bromophenolato]zinc(II)-ethanol-water (0.67/0.33/2/0.5)