Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis­(pyridine2,6-dicarboxyl­ato)zincate(II) deca­hydrate

Aghajani, Z.; Sharif, M.A.; Aghabozorg, H.; Naderpour, A.

doi:10.1107/S1600536806009688

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Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis(pyridine2,6-dicarboxylato)zincate(II) decahydrate

Z. Aghajani, M. A. Sharif, H. Aghabozorg and A. Naderpour

The reaction of zinc(II) nitrate tetrahydrate with the proton-transfer compound LH₂ [LH₂ is (tataH)₂(pydc), where tata is 2,4,6-triamino-1,3,5-triazine (melamine) and pydcH₂ is pyridine-2,6-dicarboxylic acid] in aqueous solution leads to the formation of the title compound, (tataH)₂[Zn(pydc)₂].10H₂O or (C₃H₇N₆)₂[Zn(C₇H₃O₄)₂].10H₂O. The Zn^II atom has a distorted octahedral coordination environment. Extensive intermolecular N—H

O and O—H

O hydrogen bonding involving the tataH and pydc ligands and the water molecules forms an extended three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009688/lh6589sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009688/lh6589Isup2.hkl Contains datablock I

CCDC reference: 263823

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
H-atom completeness 91%
Disorder in solvent or counterion
R factor = 0.046
wR factor = 0.114
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3BA   ..  H4WA    ..       2.06 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4WA   ..  H9WB    ..       1.85 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.35
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.39
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       6.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      >O1SA
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O1SB
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O1SC
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O8W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O8W'
PLAT430_ALERT_2_C Short Inter D...A Contact  O1SA   ..  N2A     ..       2.88 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O6     ..  O1SB    ..       2.86 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         34
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          7
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #         11
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #         12
              H2 O

Alert level G
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:C20 H40 N14 O18 Zn1
            Atom count from the _atom_site data:  C20 H36 N14 O18 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C20 H40 N14 O18 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         40.00     40.00    0.00
           H         80.00     72.00    8.00
           N         28.00     28.00    0.00
           O         36.00     36.00    0.00
           Zn         2.00      2.00    0.00

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis(pyridine2,6-dicarboxylato)zincate(II) decahydrate top

Crystal data top

(C₃H₇N₆)₂[Zn(C₇H₃NO₄)₂]·10H₂O	Z = 2
M_r = 830.03	F(000) = 864
Triclinic, P1	D_x = 1.624 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.100 (2) Å	Cell parameters from 1024 reflections
b = 12.877 (2) Å	θ = 2.3–26.6°
c = 13.209 (2) Å	µ = 0.82 mm⁻¹
α = 87.739 (4)°	T = 120 K
β = 65.731 (4)°	Cube, colourless
γ = 80.709 (3)°	0.30 × 0.30 × 0.30 mm
V = 1697.8 (5) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6529 independent reflections
Radiation source: fine-focus sealed tube	5637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→11
T_min = 0.791, T_max = 0.791	k = −15→15
10100 measured reflections	l = −13→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0428P)² + 4.8947P] where P = (F_o² + 2F_c²)/3
6529 reflections	(Δ/σ)_max < 0.001
507 parameters	Δρ_max = 1.22 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻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)
Zn1	0.14171 (3)	0.76070 (2)	0.36235 (3)	0.02286 (11)
O1	0.3038 (2)	0.77045 (15)	0.40567 (18)	0.0255 (4)
O2	0.4486 (2)	0.67223 (16)	0.46372 (19)	0.0294 (5)
O3	0.0141 (2)	0.66919 (15)	0.31813 (17)	0.0239 (4)
O4	−0.0257 (2)	0.50563 (15)	0.31099 (18)	0.0247 (4)
O5	0.2445 (2)	0.81424 (15)	0.19697 (18)	0.0259 (4)
O6	0.2388 (2)	0.95213 (17)	0.08838 (19)	0.0337 (5)
O7	−0.2061 (2)	0.89440 (17)	0.63813 (18)	0.0310 (5)
O8	−0.0170 (2)	0.78715 (15)	0.53593 (17)	0.0251 (4)
N1	0.2026 (2)	0.60773 (17)	0.38607 (19)	0.0188 (5)
N2	0.0270 (2)	0.90068 (17)	0.3609 (2)	0.0211 (5)
C1	0.3563 (3)	0.6841 (2)	0.4324 (2)	0.0219 (6)
C2	0.2983 (3)	0.5870 (2)	0.4238 (2)	0.0193 (5)
C3	0.3377 (3)	0.4853 (2)	0.4506 (2)	0.0209 (6)
H3A	0.4066	0.4708	0.4766	0.025*
C4	0.2740 (3)	0.4057 (2)	0.4381 (2)	0.0234 (6)
H4A	0.2988	0.3357	0.4561	0.028*
C5	0.1736 (3)	0.4281 (2)	0.3994 (2)	0.0220 (6)
H5A	0.1293	0.3741	0.3905	0.026*
C6	0.1401 (3)	0.5315 (2)	0.3740 (2)	0.0186 (5)
C7	0.0343 (3)	0.5714 (2)	0.3311 (2)	0.0194 (5)
C8	0.1925 (3)	0.9035 (2)	0.1758 (3)	0.0237 (6)
C9	0.0619 (3)	0.9529 (2)	0.2664 (3)	0.0232 (6)
C10	−0.0192 (3)	1.0439 (2)	0.2562 (3)	0.0249 (6)
H10A	0.0070	1.0819	0.1895	0.030*
C11	−0.1383 (3)	1.0769 (2)	0.3456 (3)	0.0271 (6)
H11A	−0.1961	1.1380	0.3404	0.032*
C12	−0.1746 (3)	1.0215 (2)	0.4435 (3)	0.0247 (6)
H12A	−0.2570	1.0435	0.5052	0.030*
C13	−0.0866 (3)	0.9326 (2)	0.4486 (2)	0.0219 (6)
C14	−0.1065 (3)	0.8665 (2)	0.5499 (3)	0.0240 (6)
N1A	0.5949 (2)	0.52564 (19)	0.1950 (2)	0.0228 (5)
N2A	0.6418 (3)	0.70279 (19)	0.1937 (2)	0.0282 (6)
N3A	0.7647 (2)	0.56125 (18)	0.2461 (2)	0.0222 (5)
H3AA	0.8300	0.5382	0.2667	0.027*
N4A	0.7178 (3)	0.3922 (2)	0.2500 (2)	0.0292 (6)
H4AA	0.6722	0.3467	0.2400	0.035*
H4AB	0.7813	0.3708	0.2732	0.035*
N5A	0.4829 (3)	0.6650 (2)	0.1400 (2)	0.0300 (6)
H5AA	0.4370	0.6210	0.1278	0.036*
H5AB	0.4673	0.7324	0.1274	0.036*
N6A	0.8033 (3)	0.7314 (2)	0.2508 (3)	0.0357 (7)
H6AA	0.7865	0.7994	0.2410	0.043*
H6AB	0.8653	0.7069	0.2747	0.043*
C1A	0.6910 (3)	0.4925 (2)	0.2302 (2)	0.0223 (6)
C2A	0.5754 (3)	0.6298 (2)	0.1772 (2)	0.0234 (6)
C3A	0.7351 (3)	0.6662 (2)	0.2296 (3)	0.0250 (6)
N1B	0.1354 (2)	0.5261 (2)	0.0365 (2)	0.0272 (5)
N2B	0.3155 (3)	0.5357 (2)	0.0914 (2)	0.0280 (6)
N3B	0.2362 (3)	0.3762 (2)	0.0981 (2)	0.0301 (6)
H3BA	0.2403	0.3089	0.1135	0.036*
N4B	0.0594 (3)	0.3682 (2)	0.0508 (2)	0.0360 (7)
H4BA	−0.0010	0.3978	0.0269	0.043*
H4BB	0.0640	0.3012	0.0673	0.043*
N5B	0.2170 (3)	0.6792 (2)	0.0310 (2)	0.0355 (7)
H5BA	0.1583	0.7102	0.0060	0.043*
H5BB	0.2721	0.7156	0.0410	0.043*
N6B	0.4146 (3)	0.3857 (2)	0.1434 (2)	0.0316 (6)
H6BA	0.4703	0.4215	0.1531	0.038*
H6BB	0.4196	0.3178	0.1559	0.038*
C1B	0.1434 (3)	0.4246 (3)	0.0618 (2)	0.0287 (7)
C2B	0.2223 (3)	0.5784 (3)	0.0534 (2)	0.0269 (6)
C3B	0.3231 (3)	0.4338 (2)	0.1101 (2)	0.0259 (6)
O1W	−0.0611 (2)	0.30500 (16)	0.3026 (2)	0.0352 (5)
H1WA	−0.0411	0.3652	0.3068	0.048 (12)*
H1WB	−0.0374	0.2665	0.3470	0.052 (12)*
O2W	0.5805 (2)	1.05755 (17)	0.7168 (2)	0.0348 (5)
H2WA	0.6493	1.0103	0.6910	0.052*
H2WB	0.6189	1.1078	0.6812	0.052*
O3W	1.5088 (3)	0.84707 (18)	0.5300 (2)	0.0417 (6)
H3WA	1.5737	0.8655	0.4742	0.063*
H3WB	1.4941	0.7953	0.5011	0.063*
O4W	0.2581 (3)	0.1725 (2)	0.1521 (2)	0.0473 (6)
H4WB	0.2363	0.1503	0.2178	0.071*
H4WA	0.3427	0.1653	0.1295	0.071*
O5W	0.6294 (2)	0.96777 (19)	0.3303 (2)	0.0431 (6)
H5WB	0.6035	1.0252	0.3683	0.065*
H5WA	0.5682	0.9617	0.3091	0.065*
O6W	0.0367 (3)	0.8326 (2)	−0.0271 (2)	0.0490 (7)
H6WA	−0.0410	0.8598	0.0188	0.074*
H6WB	0.0823	0.8796	−0.0627	0.074*
O7W	1.4348 (3)	0.7684 (2)	−0.2522 (2)	0.0628 (9)
H7WA	1.4705	0.8028	−0.3103	0.094*
H7WB	1.4440	0.7984	−0.2002	0.094*
O8W	0.1819 (3)	1.0121 (2)	0.8896 (3)	0.0453 (8)	0.80
O8W'	0.2508 (13)	0.9056 (10)	0.8694 (10)	0.043 (3)	0.20
O9W	1.5422 (4)	1.1483 (3)	0.0769 (3)	0.0731 (10)
H9WB	1.5113	1.0916	0.1001	0.110*
H9WA	1.6129	1.1250	0.0205	0.110*
O1SA	0.3858 (4)	1.1079 (3)	0.9235 (3)	0.0331 (8)	0.60
O1SB	0.4845 (12)	1.1134 (10)	0.9596 (10)	0.038 (3)	0.20
O1SC	0.2267 (15)	1.1276 (10)	0.9404 (11)	0.049 (3)	0.20

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02697 (19)	0.01378 (16)	0.0360 (2)	−0.00261 (12)	−0.02138 (16)	0.00179 (13)
O1	0.0307 (11)	0.0154 (9)	0.0405 (12)	−0.0051 (8)	−0.0243 (10)	0.0020 (8)
O2	0.0344 (12)	0.0211 (10)	0.0487 (14)	−0.0067 (9)	−0.0324 (11)	0.0037 (9)
O3	0.0283 (11)	0.0170 (9)	0.0361 (12)	−0.0048 (8)	−0.0225 (10)	0.0016 (8)
O4	0.0300 (11)	0.0188 (9)	0.0366 (12)	−0.0081 (8)	−0.0235 (10)	0.0022 (8)
O5	0.0278 (11)	0.0199 (10)	0.0341 (12)	−0.0031 (8)	−0.0172 (9)	0.0031 (8)
O6	0.0339 (12)	0.0295 (11)	0.0387 (13)	−0.0063 (9)	−0.0162 (11)	0.0098 (10)
O7	0.0340 (12)	0.0269 (11)	0.0335 (12)	−0.0005 (9)	−0.0170 (11)	0.0046 (9)
O8	0.0318 (11)	0.0166 (9)	0.0346 (12)	−0.0016 (8)	−0.0222 (10)	0.0030 (8)
N1	0.0220 (11)	0.0160 (11)	0.0214 (12)	−0.0020 (9)	−0.0121 (10)	−0.0016 (9)
N2	0.0261 (12)	0.0152 (11)	0.0312 (13)	−0.0060 (9)	−0.0199 (11)	0.0016 (9)
C1	0.0245 (14)	0.0179 (13)	0.0289 (15)	−0.0038 (11)	−0.0162 (13)	−0.0004 (11)
C2	0.0208 (13)	0.0172 (13)	0.0222 (14)	−0.0030 (10)	−0.0112 (12)	−0.0014 (10)
C3	0.0222 (14)	0.0197 (13)	0.0241 (14)	−0.0015 (11)	−0.0134 (12)	0.0008 (11)
C4	0.0279 (15)	0.0149 (13)	0.0295 (15)	−0.0026 (11)	−0.0145 (13)	0.0029 (11)
C5	0.0263 (14)	0.0169 (13)	0.0266 (15)	−0.0071 (11)	−0.0133 (12)	0.0022 (11)
C6	0.0199 (13)	0.0183 (13)	0.0196 (13)	−0.0043 (10)	−0.0096 (11)	−0.0003 (10)
C7	0.0216 (13)	0.0183 (13)	0.0212 (14)	−0.0042 (10)	−0.0115 (12)	0.0013 (10)
C8	0.0264 (15)	0.0200 (13)	0.0332 (16)	−0.0087 (11)	−0.0191 (13)	0.0029 (12)
C9	0.0287 (15)	0.0180 (13)	0.0331 (16)	−0.0082 (11)	−0.0213 (13)	0.0014 (11)
C10	0.0329 (16)	0.0183 (13)	0.0342 (16)	−0.0065 (12)	−0.0239 (14)	0.0034 (11)
C11	0.0337 (16)	0.0148 (13)	0.0436 (18)	−0.0029 (11)	−0.0271 (15)	0.0013 (12)
C12	0.0281 (15)	0.0199 (13)	0.0333 (16)	−0.0028 (11)	−0.0199 (14)	−0.0018 (12)
C13	0.0263 (15)	0.0173 (13)	0.0310 (16)	−0.0064 (11)	−0.0194 (13)	−0.0001 (11)
C14	0.0278 (15)	0.0192 (13)	0.0340 (17)	−0.0062 (11)	−0.0207 (14)	0.0016 (12)
N1A	0.0226 (12)	0.0257 (12)	0.0243 (12)	−0.0047 (10)	−0.0133 (10)	−0.0010 (10)
N2A	0.0315 (14)	0.0230 (12)	0.0413 (15)	−0.0041 (10)	−0.0265 (13)	0.0025 (11)
N3A	0.0243 (12)	0.0218 (12)	0.0270 (13)	−0.0033 (9)	−0.0170 (11)	0.0004 (9)
N4A	0.0338 (14)	0.0249 (13)	0.0401 (15)	−0.0098 (11)	−0.0250 (13)	0.0056 (11)
N5A	0.0312 (14)	0.0254 (13)	0.0463 (16)	−0.0043 (11)	−0.0288 (13)	0.0009 (11)
N6A	0.0425 (16)	0.0205 (13)	0.066 (2)	−0.0063 (11)	−0.0433 (16)	0.0045 (12)
C1A	0.0222 (14)	0.0256 (14)	0.0219 (14)	−0.0052 (11)	−0.0113 (12)	0.0012 (11)
C2A	0.0225 (14)	0.0262 (14)	0.0241 (15)	−0.0031 (11)	−0.0122 (12)	−0.0015 (11)
C3A	0.0270 (15)	0.0238 (14)	0.0306 (16)	−0.0036 (12)	−0.0182 (13)	−0.0011 (12)
N1B	0.0224 (12)	0.0410 (15)	0.0234 (13)	−0.0082 (11)	−0.0135 (11)	0.0009 (11)
N2B	0.0243 (13)	0.0360 (14)	0.0302 (14)	−0.0022 (11)	−0.0180 (11)	−0.0057 (11)
N3B	0.0280 (13)	0.0388 (15)	0.0327 (14)	−0.0140 (11)	−0.0192 (12)	0.0098 (11)
N4B	0.0331 (15)	0.0479 (17)	0.0410 (16)	−0.0196 (13)	−0.0255 (13)	0.0137 (13)
N5B	0.0376 (15)	0.0319 (14)	0.0521 (18)	−0.0010 (12)	−0.0343 (15)	−0.0071 (13)
N6B	0.0291 (14)	0.0383 (15)	0.0375 (15)	−0.0093 (11)	−0.0229 (12)	0.0072 (12)
C1B	0.0242 (15)	0.0460 (19)	0.0202 (14)	−0.0122 (13)	−0.0114 (12)	0.0052 (13)
C2B	0.0245 (15)	0.0369 (17)	0.0227 (15)	−0.0024 (12)	−0.0132 (13)	−0.0074 (12)
C3B	0.0214 (14)	0.0371 (17)	0.0211 (14)	−0.0063 (12)	−0.0100 (12)	−0.0001 (12)
O1W	0.0558 (15)	0.0185 (10)	0.0528 (15)	−0.0117 (10)	−0.0423 (13)	0.0087 (10)
O2W	0.0321 (12)	0.0230 (11)	0.0551 (15)	−0.0063 (9)	−0.0231 (11)	0.0019 (10)
O3W	0.0571 (16)	0.0308 (12)	0.0485 (15)	−0.0160 (11)	−0.0292 (13)	−0.0038 (11)
O4W	0.0502 (16)	0.0526 (16)	0.0330 (13)	0.0016 (13)	−0.0146 (12)	0.0022 (11)
O5W	0.0390 (14)	0.0326 (13)	0.0702 (18)	−0.0076 (10)	−0.0337 (13)	−0.0027 (12)
O6W	0.0426 (15)	0.0608 (17)	0.0462 (15)	0.0009 (13)	−0.0247 (13)	0.0082 (13)
O7W	0.099 (2)	0.0523 (17)	0.0429 (16)	−0.0465 (17)	−0.0224 (16)	0.0034 (13)
O8W	0.0445 (18)	0.0399 (17)	0.063 (2)	0.0037 (14)	−0.0364 (17)	−0.0144 (15)
O8W'	0.043 (7)	0.046 (7)	0.039 (7)	−0.015 (6)	−0.015 (6)	0.000 (6)
O9W	0.068 (2)	0.078 (2)	0.072 (2)	0.0022 (18)	−0.0317 (19)	−0.0182 (18)
O1SA	0.044 (2)	0.0251 (18)	0.0274 (19)	−0.0055 (16)	−0.0112 (17)	0.0001 (14)
O1SB	0.034 (6)	0.040 (7)	0.036 (7)	−0.004 (5)	−0.010 (5)	0.002 (5)
O1SC	0.071 (10)	0.040 (7)	0.047 (8)	−0.016 (7)	−0.032 (7)	0.011 (6)

Geometric parameters (Å, º) top

Zn1—N1	2.032 (2)	N4A—H4AA	0.8800
Zn1—N2	2.036 (2)	N4A—H4AB	0.8800
Zn1—O1	2.123 (2)	N5A—C2A	1.322 (4)
Zn1—O5	2.153 (2)	N5A—H5AA	0.8800
Zn1—O3	2.2381 (19)	N5A—H5AB	0.8800
Zn1—O8	2.241 (2)	N6A—C3A	1.325 (4)
O1—C1	1.276 (3)	N6A—H6AA	0.8800
O2—C1	1.239 (3)	N6A—H6AB	0.8800
O3—C7	1.260 (3)	N1B—C1B	1.334 (4)
O4—C7	1.256 (3)	N1B—C2B	1.354 (4)
O5—C8	1.276 (3)	N2B—C3B	1.320 (4)
O6—C8	1.244 (4)	N2B—C2B	1.359 (4)
O7—C14	1.247 (4)	N3B—C1B	1.362 (4)
O8—C14	1.265 (3)	N3B—C3B	1.368 (4)
N1—C2	1.335 (4)	N3B—H3BA	0.8800
N1—C6	1.339 (3)	N4B—C1B	1.326 (4)
N2—C13	1.330 (4)	N4B—H4BA	0.8800
N2—C9	1.335 (4)	N4B—H4BB	0.8800
C1—C2	1.524 (4)	N5B—C2B	1.317 (4)
C2—C3	1.391 (4)	N5B—H5BA	0.8800
C3—C4	1.386 (4)	N5B—H5BB	0.8800
C3—H3A	0.9500	N6B—C3B	1.324 (4)
C4—C5	1.393 (4)	N6B—H6BA	0.8800
C4—H4A	0.9500	N6B—H6BB	0.8800
C5—C6	1.390 (4)	O1W—H1WA	0.8499
C5—H5A	0.9500	O1W—H1WB	0.8498
C6—C7	1.514 (4)	O2W—H2WA	0.8499
C8—C9	1.508 (4)	O2W—H2WB	0.8502
C9—C10	1.395 (4)	O3W—H3WA	0.8500
C10—C11	1.378 (5)	O3W—H3WB	0.8500
C10—H10A	0.9500	O4W—H4WB	0.8500
C11—C12	1.391 (4)	O4W—H4WA	0.8500
C11—H11A	0.9500	O5W—H5WB	0.8501
C12—C13	1.399 (4)	O5W—H5WA	0.8499
C12—H12A	0.9500	O6W—H6WA	0.8500
C13—C14	1.514 (4)	O6W—H6WB	0.8500
N1A—C1A	1.335 (4)	O7W—H7WA	0.8501
N1A—C2A	1.350 (4)	O7W—H7WB	0.8501
N2A—C3A	1.322 (4)	O8W—O8W'	1.434 (14)
N2A—C2A	1.359 (4)	O9W—H9WB	0.8500
N3A—C3A	1.368 (4)	O9W—H9WA	0.8500
N3A—C1A	1.373 (4)	O1SA—O1SB	1.375 (13)
N3A—H3AA	0.8800	O1SA—O1SC	1.663 (15)
N4A—C1A	1.319 (4)

N1—Zn1—N2	163.14 (9)	N2—C13—C12	120.6 (3)
N1—Zn1—O1	77.47 (8)	N2—C13—C14	114.1 (2)
N2—Zn1—O1	115.34 (8)	C12—C13—C14	125.3 (3)
N1—Zn1—O5	114.87 (9)	O7—C14—O8	126.2 (3)
N2—Zn1—O5	76.83 (9)	O7—C14—C13	118.5 (2)
O1—Zn1—O5	92.87 (8)	O8—C14—C13	115.3 (3)
N1—Zn1—O3	74.84 (8)	C1A—N1A—C2A	115.7 (2)
N2—Zn1—O3	92.57 (8)	C3A—N2A—C2A	115.5 (2)
O1—Zn1—O3	152.04 (7)	C3A—N3A—C1A	119.1 (2)
O5—Zn1—O3	95.28 (8)	C3A—N3A—H3AA	120.4
N1—Zn1—O8	93.89 (8)	C1A—N3A—H3AA	120.4
N2—Zn1—O8	74.65 (9)	C1A—N4A—H4AA	120.0
O1—Zn1—O8	95.45 (8)	C1A—N4A—H4AB	120.0
O5—Zn1—O8	151.16 (7)	H4AA—N4A—H4AB	120.0
O3—Zn1—O8	90.17 (8)	C2A—N5A—H5AA	120.0
C1—O1—Zn1	115.68 (17)	C2A—N5A—H5AB	120.0
C7—O3—Zn1	114.69 (17)	H5AA—N5A—H5AB	120.0
C8—O5—Zn1	115.28 (19)	C3A—N6A—H6AA	120.0
C14—O8—Zn1	115.06 (19)	C3A—N6A—H6AB	120.0
C2—N1—C6	121.0 (2)	H6AA—N6A—H6AB	120.0
C2—N1—Zn1	117.82 (18)	N4A—C1A—N1A	120.4 (3)
C6—N1—Zn1	120.85 (18)	N4A—C1A—N3A	118.4 (3)
C13—N2—C9	121.5 (2)	N1A—C1A—N3A	121.2 (3)
C13—N2—Zn1	120.10 (19)	N5A—C2A—N1A	117.4 (3)
C9—N2—Zn1	118.0 (2)	N5A—C2A—N2A	116.2 (3)
O2—C1—O1	126.5 (3)	N1A—C2A—N2A	126.4 (3)
O2—C1—C2	117.9 (2)	N2A—C3A—N6A	120.2 (3)
O1—C1—C2	115.6 (2)	N2A—C3A—N3A	121.9 (3)
N1—C2—C3	121.2 (2)	N6A—C3A—N3A	117.9 (3)
N1—C2—C1	113.1 (2)	C1B—N1B—C2B	115.5 (3)
C3—C2—C1	125.7 (2)	C3B—N2B—C2B	116.4 (3)
C4—C3—C2	118.3 (3)	C1B—N3B—C3B	118.8 (3)
C4—C3—H3A	120.9	C1B—N3B—H3BA	120.6
C2—C3—H3A	120.9	C3B—N3B—H3BA	120.6
C3—C4—C5	120.2 (2)	C1B—N4B—H4BA	120.0
C3—C4—H4A	119.9	C1B—N4B—H4BB	120.0
C5—C4—H4A	119.9	H4BA—N4B—H4BB	120.0
C6—C5—C4	118.2 (2)	C2B—N5B—H5BA	120.0
C6—C5—H5A	120.9	C2B—N5B—H5BB	120.0
C4—C5—H5A	120.9	H5BA—N5B—H5BB	120.0
N1—C6—C5	121.1 (2)	C3B—N6B—H6BA	120.0
N1—C6—C7	112.8 (2)	C3B—N6B—H6BB	120.0
C5—C6—C7	126.1 (2)	H6BA—N6B—H6BB	120.0
O4—C7—O3	125.2 (2)	N4B—C1B—N1B	119.4 (3)
O4—C7—C6	118.2 (2)	N4B—C1B—N3B	118.4 (3)
O3—C7—C6	116.6 (2)	N1B—C1B—N3B	122.1 (3)
O6—C8—O5	126.2 (3)	N5B—C2B—N1B	117.7 (3)
O6—C8—C9	118.0 (3)	N5B—C2B—N2B	116.9 (3)
O5—C8—C9	115.7 (3)	N1B—C2B—N2B	125.5 (3)
N2—C9—C10	121.1 (3)	N2B—C3B—N6B	120.0 (3)
N2—C9—C8	113.8 (2)	N2B—C3B—N3B	121.5 (3)
C10—C9—C8	125.1 (3)	N6B—C3B—N3B	118.4 (3)
C11—C10—C9	118.1 (3)	H1WA—O1W—H1WB	106.2
C11—C10—H10A	120.9	H2WA—O2W—H2WB	96.0
C9—C10—H10A	120.9	H3WA—O3W—H3WB	100.1
C10—C11—C12	120.4 (3)	H4WB—O4W—H4WA	100.8
C10—C11—H11A	119.8	H5WB—O5W—H5WA	105.8
C12—C11—H11A	119.8	H6WA—O6W—H6WB	111.5
C11—C12—C13	118.2 (3)	H7WA—O7W—H7WB	106.4
C11—C12—H12A	120.9	H9WB—O9W—H9WA	100.6
C13—C12—H12A	120.9	O1SB—O1SA—O1SC	152.3 (7)

N1—Zn1—O1—C1	−4.3 (2)	C4—C5—C6—N1	0.2 (4)
N2—Zn1—O1—C1	164.1 (2)	C4—C5—C6—C7	−180.0 (3)
O5—Zn1—O1—C1	−119.2 (2)	Zn1—O3—C7—O4	−179.7 (2)
O3—Zn1—O1—C1	−12.2 (3)	Zn1—O3—C7—C6	0.0 (3)
O8—Zn1—O1—C1	88.5 (2)	N1—C6—C7—O4	176.3 (2)
N1—Zn1—O3—C7	2.16 (19)	C5—C6—C7—O4	−3.6 (4)
N2—Zn1—O3—C7	−166.5 (2)	N1—C6—C7—O3	−3.5 (4)
O1—Zn1—O3—C7	10.2 (3)	C5—C6—C7—O3	176.6 (3)
O5—Zn1—O3—C7	116.5 (2)	Zn1—O5—C8—O6	175.7 (2)
O8—Zn1—O3—C7	−91.8 (2)	Zn1—O5—C8—C9	−4.8 (3)
N1—Zn1—O5—C8	168.53 (18)	C13—N2—C9—C10	0.7 (4)
N2—Zn1—O5—C8	1.41 (19)	Zn1—N2—C9—C10	173.7 (2)
O1—Zn1—O5—C8	−113.95 (19)	C13—N2—C9—C8	−178.8 (2)
O3—Zn1—O5—C8	92.82 (19)	Zn1—N2—C9—C8	−5.8 (3)
O8—Zn1—O5—C8	−7.2 (3)	O6—C8—C9—N2	−173.4 (2)
N1—Zn1—O8—C14	−161.39 (19)	O5—C8—C9—N2	7.0 (3)
N2—Zn1—O8—C14	6.04 (19)	O6—C8—C9—C10	7.1 (4)
O1—Zn1—O8—C14	120.85 (19)	O5—C8—C9—C10	−172.5 (3)
O5—Zn1—O8—C14	14.7 (3)	N2—C9—C10—C11	−1.8 (4)
O3—Zn1—O8—C14	−86.58 (19)	C8—C9—C10—C11	177.7 (3)
N2—Zn1—N1—C2	−135.7 (3)	C9—C10—C11—C12	1.1 (4)
O1—Zn1—N1—C2	5.4 (2)	C10—C11—C12—C13	0.6 (4)
O5—Zn1—N1—C2	92.8 (2)	C9—N2—C13—C12	1.1 (4)
O3—Zn1—N1—C2	−178.4 (2)	Zn1—N2—C13—C12	−171.8 (2)
O8—Zn1—N1—C2	−89.3 (2)	C9—N2—C13—C14	−177.5 (2)
N2—Zn1—N1—C6	38.3 (4)	Zn1—N2—C13—C14	9.7 (3)
O1—Zn1—N1—C6	179.4 (2)	C11—C12—C13—N2	−1.7 (4)
O5—Zn1—N1—C6	−93.2 (2)	C11—C12—C13—C14	176.7 (3)
O3—Zn1—N1—C6	−4.4 (2)	Zn1—O8—C14—O7	177.7 (2)
O8—Zn1—N1—C6	84.7 (2)	Zn1—O8—C14—C13	−3.1 (3)
N1—Zn1—N2—C13	40.0 (4)	N2—C13—C14—O7	175.6 (2)
O1—Zn1—N2—C13	−97.3 (2)	C12—C13—C14—O7	−2.9 (4)
O5—Zn1—N2—C13	175.8 (2)	N2—C13—C14—O8	−3.7 (3)
O3—Zn1—N2—C13	81.0 (2)	C12—C13—C14—O8	177.8 (3)
O8—Zn1—N2—C13	−8.50 (19)	C2A—N1A—C1A—N4A	180.0 (3)
N1—Zn1—N2—C9	−133.1 (3)	C2A—N1A—C1A—N3A	−0.4 (4)
O1—Zn1—N2—C9	89.6 (2)	C3A—N3A—C1A—N4A	−177.8 (3)
O5—Zn1—N2—C9	2.71 (19)	C3A—N3A—C1A—N1A	2.5 (4)
O3—Zn1—N2—C9	−92.1 (2)	C1A—N1A—C2A—N5A	178.6 (3)
O8—Zn1—N2—C9	178.4 (2)	C1A—N1A—C2A—N2A	−1.3 (4)
Zn1—O1—C1—O2	−177.6 (3)	C3A—N2A—C2A—N5A	−179.2 (3)
Zn1—O1—C1—C2	2.7 (3)	C3A—N2A—C2A—N1A	0.7 (5)
C6—N1—C2—C3	0.8 (4)	C2A—N2A—C3A—N6A	−178.3 (3)
Zn1—N1—C2—C3	174.8 (2)	C2A—N2A—C3A—N3A	1.6 (4)
C6—N1—C2—C1	−179.6 (2)	C1A—N3A—C3A—N2A	−3.2 (4)
Zn1—N1—C2—C1	−5.6 (3)	C1A—N3A—C3A—N6A	176.7 (3)
O2—C1—C2—N1	−178.0 (3)	C2B—N1B—C1B—N4B	178.1 (3)
O1—C1—C2—N1	1.8 (4)	C2B—N1B—C1B—N3B	−2.4 (4)
O2—C1—C2—C3	1.6 (4)	C3B—N3B—C1B—N4B	−179.8 (3)
O1—C1—C2—C3	−178.7 (3)	C3B—N3B—C1B—N1B	0.7 (4)
N1—C2—C3—C4	−0.7 (4)	C1B—N1B—C2B—N5B	−179.1 (3)
C1—C2—C3—C4	179.8 (3)	C1B—N1B—C2B—N2B	1.1 (4)
C2—C3—C4—C5	0.3 (4)	C3B—N2B—C2B—N5B	−177.8 (3)
C3—C4—C5—C6	0.0 (4)	C3B—N2B—C2B—N1B	2.0 (4)
C2—N1—C6—C5	−0.6 (4)	C2B—N2B—C3B—N6B	177.6 (3)
Zn1—N1—C6—C5	−174.4 (2)	C2B—N2B—C3B—N3B	−3.8 (4)
C2—N1—C6—C7	179.5 (2)	C1B—N3B—C3B—N2B	2.6 (4)
Zn1—N1—C6—C7	5.7 (3)	C1B—N3B—C3B—N6B	−178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3AA···O4ⁱ	0.88	1.90	2.777 (3)	173
N4A—H4AA···O7Wⁱⁱ	0.88	2.01	2.870 (4)	167
N4A—H4AB···O1Wⁱ	0.88	2.00	2.866 (3)	170
N5A—H5AA···N2B	0.88	2.08	2.950 (3)	172
N5A—H5AB···O5	0.88	2.33	2.846 (3)	117
N6A—H6AB···O3ⁱ	0.88	1.95	2.821 (3)	172
N3B—H3BA···O4W	0.88	1.81	2.690 (3)	175
N4B—H4BA···N1Bⁱⁱⁱ	0.88	2.09	2.972 (3)	176
N4B—H4BB···O6Wⁱⁱⁱ	0.88	2.38	3.026 (4)	130
N5B—H5BA···O6W	0.88	2.06	2.891 (4)	157
N5B—H5BB···O5	0.88	2.35	2.991 (3)	130
N6B—H6BA···N1A	0.88	2.30	3.179 (3)	173
N6B—H6BB···O9W^iv	0.88	2.40	3.148 (4)	143
N6B—H6BB···O7Wⁱⁱ	0.88	2.54	3.078 (3)	120
O1W—H1WA···O4	0.85	1.85	2.688 (3)	169
O1W—H1WB···O8^v	0.85	1.94	2.775 (3)	165
O2W—H2WA···O7ⁱ	0.85	1.92	2.765 (3)	175
O2W—H2WB···O1^vi	0.85	2.00	2.846 (3)	175
O3W—H3WA···O5Wⁱ	0.85	2.20	2.934 (3)	145
O3W—H3WB···O2ⁱ	0.85	1.88	2.721 (3)	170
O4W—H4WB···O7^v	0.85	1.88	2.722 (3)	174
O4W—H4WA···O9W^iv	0.85	2.01	2.857 (4)	180
O4W—H4WA···O1SB^vii	0.85	2.20	2.764 (4)	124
O5W—H5WB···O3W^viii	0.85	2.05	2.878 (3)	165
O5W—H5WA···O2W^vi	0.85	1.87	2.716 (3)	172
O6W—H6WA···O1SC^ix	0.85	1.89	2.634 (5)	146
O6W—H6WA···O8W^ix	0.85	2.10	2.878 (4)	152
O6W—H6WB···O8W′^x	0.85	1.79	2.519 (4)	142
O6W—H6WB···O8W^x	0.85	2.12	2.947 (4)	165
O7W—H7WA···O3W^x	0.85	2.05	2.842 (3)	155
O7W—H7WB···O9W^xi	0.85	1.86	2.710 (4)	174
O9W—H9WA···O6^xii	0.85	1.84	2.682 (4)	168

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z; (iii) −x, −y+1, −z; (iv) x−1, y−1, z; (v) −x, −y+1, −z+1; (vi) −x+1, −y+2, −z+1; (vii) x, y−1, z−1; (viii) −x+2, −y+2, −z+1; (ix) −x, −y+2, −z+1; (x) x, y, z−1; (xi) −x+3, −y+2, −z; (xii) −x+2, −y+2, −z.

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