Infinite hydrogen-bonded chains in tris­(1,10-phenanthroline)zinc(II) nitrate bis­(glutaric acid) dihydrate

The cation of the title complex, [Zn(C₁₂H₈N₂)₃](NO₃)₂·2C₅H₈O₄·2H₂O, contains a six-coordinate Zn atom with a distorted octa­hedral geometry, with three 1,10-phenanthroline mol­ecules as bidentate ligands, and lies on a twofold rotation axis. The asymmetric unit also contains an uncoordinated nitrate anion, a glutaric acid mol­ecule and a water mol­ecule. The anions and neutral mol­ecules of the crystal structure are connected together by O—H...O hydrogen bonds, forming infinite chains, and the complex cations are located between the chains.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.036
• wR factor = 0.065
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N4
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      12.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT733_ALERT_1_C Torsion Calc    -53.6(4), Rep  -53.58(12) ......       3.33 su-Rat
              N2  -ZN1 -N2  -C11    2.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.50 Deg.
              O6B  -N4   -O6A     1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C5 H8 O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              N O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

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

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

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Computing details

Data collection: P3/PC (Siemens, 1989); cell refinement: P3/PC; data reduction: P3/PC; 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.

tris(1,10-phenanthroline)zinc(II) nitrate bis(glutaric acid) dihydrate

Crystal data

[Zn(C12H8N2)3](NO3)2·2C5H8O4·2H2O	F(000) = 2136
Mr = 1030.28	Dx = 1.456 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 24 reflections
a = 21.923 (4) Å	θ = 8–14°
b = 14.532 (3) Å	µ = 0.60 mm^−1
c = 14.820 (3) Å	T = 193 K
β = 95.351 (14)°	Prism, orange
V = 4700.9 (15) Å^3	0.2 × 0.15 × 0.1 mm
Z = 4

Data collection

Rebuilt Syntex P21/Siemens P3 four-circle diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.7°
Graphite monochromator	h = −11→28
ω/2θ scans	k = −14→18
5202 measured reflections	l = −18→18
5067 independent reflections	2 standard reflections every 98 reflections
3736 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.036	Hydrogen site location: mixed
wR(F^2) = 0.066	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.004P)^2] where P = (Fo^2 + 2Fc^2)/3
5067 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.27 e Å^−3
1 restraint	Δρmin = −0.30 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	0.0000	0.73212 (2)	0.2500	0.02714 (8)
O1	−0.14680 (7)	0.75810 (13)	0.74715 (10)	0.0618 (5)
O2	−0.24530 (7)	0.72915 (13)	0.71339 (10)	0.0607 (5)
H2	−0.2465	0.7222	0.7681	0.091*
O3	−0.06821 (7)	1.02790 (10)	0.55183 (9)	0.0418 (4)
H3	−0.0391	1.0520	0.5301	0.063*
O4	−0.03246 (7)	0.89612 (10)	0.50080 (9)	0.0403 (4)
O5	−0.27218 (8)	1.02257 (13)	0.91832 (14)	0.0705 (6)
O6A	−0.30714 (11)	0.88776 (17)	0.9376 (2)	0.0556 (7)	0.75
O7A	−0.21506 (12)	0.92337 (18)	0.9851 (2)	0.0862 (10)	0.75
O6B	−0.2934 (5)	0.8860 (8)	0.9799 (7)	0.081 (4)*	0.25
O7B	−0.2313 (5)	0.8980 (5)	0.8935 (7)	0.104 (3)	0.25
N1	−0.05780 (7)	0.84707 (11)	0.27448 (9)	0.0265 (3)
N2	0.03378 (7)	0.71777 (10)	0.39154 (10)	0.0275 (4)
N3	0.06276 (8)	0.63367 (11)	0.20103 (10)	0.0307 (4)
N4	−0.26383 (9)	0.94350 (15)	0.94210 (14)	0.0468 (5)
C1	−0.11436 (9)	0.84711 (14)	0.30069 (12)	0.0305 (4)
H1A	−0.1343	0.7896	0.3065	0.037*
C2	−0.14563 (9)	0.92641 (14)	0.31989 (13)	0.0351 (5)
H2A	−0.1856	0.9229	0.3395	0.042*
C3	−0.11815 (9)	1.01004 (15)	0.31031 (13)	0.0342 (5)
H3A	−0.1389	1.0652	0.3233	0.041*
C4	−0.05893 (9)	1.01358 (13)	0.28110 (12)	0.0290 (4)
C5	−0.03045 (8)	0.92989 (12)	0.26476 (11)	0.0245 (4)
C6	−0.02768 (9)	1.09792 (13)	0.26570 (13)	0.0355 (5)
H6A	−0.0466	1.1548	0.2780	0.043*
C7	0.08121 (9)	0.75863 (13)	0.43619 (12)	0.0320 (4)
H7A	0.1063	0.7970	0.4033	0.038*
C8	0.09640 (9)	0.74829 (14)	0.52941 (13)	0.0367 (5)
H8A	0.1312	0.7785	0.5588	0.044*
C9	0.06029 (10)	0.69402 (14)	0.57721 (13)	0.0369 (5)
H9A	0.0698	0.6863	0.6406	0.044*
C10	0.00906 (9)	0.64952 (14)	0.53303 (12)	0.0324 (5)
C11	−0.00219 (9)	0.66354 (13)	0.43899 (12)	0.0281 (4)
C12	0.10933 (10)	0.59118 (14)	0.24712 (14)	0.0390 (5)
H12A	0.1161	0.6018	0.3105	0.047*
C13	0.14887 (11)	0.53157 (16)	0.20707 (15)	0.0472 (6)
H13A	0.1814	0.5020	0.2427	0.057*
C14	0.13995 (11)	0.51657 (16)	0.11611 (15)	0.0463 (6)
H14A	0.1664	0.4762	0.0877	0.056*
C15	0.09173 (10)	0.56064 (14)	0.06436 (13)	0.0353 (5)
C16	0.05378 (9)	0.61850 (13)	0.11001 (12)	0.0293 (4)
C17	0.07919 (10)	0.54842 (15)	−0.03155 (14)	0.0405 (5)
H17A	0.1051	0.5100	−0.0631	0.049*
C18	0.03116 (10)	0.59063 (15)	−0.07752 (14)	0.0401 (5)
H18A	0.0238	0.5811	−0.1410	0.048*
C19	−0.18981 (10)	0.74723 (15)	0.69192 (14)	0.0398 (5)
C20	−0.18764 (10)	0.75029 (15)	0.59150 (13)	0.0437 (6)
H20A	−0.2231	0.7864	0.5647	0.052*
H20B	−0.1921	0.6868	0.5675	0.052*
C21	−0.12914 (10)	0.79199 (14)	0.56012 (15)	0.0423 (5)
H21A	−0.0933	0.7678	0.5984	0.051*
H21B	−0.1251	0.7728	0.4969	0.051*
C22	−0.12890 (9)	0.89590 (13)	0.56513 (13)	0.0341 (5)
H22A	−0.1645	0.9197	0.5261	0.041*
H22B	−0.1340	0.9147	0.6282	0.041*
C23	−0.07189 (10)	0.93914 (14)	0.53654 (13)	0.0323 (5)
O1W	−0.26836 (8)	0.71542 (12)	0.88169 (11)	0.0662 (5)
H1W1	−0.2639	0.6785	0.9236	0.099*
H1W2	−0.2740	0.7646	0.9068	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02901 (17)	0.02630 (16)	0.02664 (16)	0.000	0.00545 (13)	0.000
O1	0.0401 (9)	0.0961 (15)	0.0466 (9)	−0.0272 (10)	−0.0106 (7)	0.0186 (10)
O2	0.0362 (9)	0.0974 (14)	0.0483 (9)	−0.0233 (10)	0.0021 (7)	−0.0006 (10)
O3	0.0475 (9)	0.0312 (8)	0.0486 (9)	−0.0022 (7)	0.0146 (7)	−0.0044 (7)
O4	0.0418 (9)	0.0343 (8)	0.0463 (9)	0.0007 (7)	0.0112 (7)	−0.0026 (7)
O5	0.0569 (12)	0.0467 (11)	0.1118 (16)	0.0071 (9)	0.0290 (11)	0.0203 (11)
O6A	0.0330 (14)	0.0411 (14)	0.091 (2)	−0.0072 (11)	−0.0009 (15)	−0.0061 (15)
O7A	0.0476 (16)	0.0602 (17)	0.142 (3)	−0.0138 (13)	−0.0396 (17)	0.0228 (18)
O7B	0.109 (8)	0.076 (6)	0.142 (9)	−0.007 (6)	0.081 (7)	−0.014 (6)
N1	0.0245 (8)	0.0303 (9)	0.0250 (8)	−0.0009 (7)	0.0036 (6)	−0.0009 (7)
N2	0.0278 (8)	0.0264 (9)	0.0288 (8)	0.0018 (7)	0.0061 (7)	−0.0015 (7)
N3	0.0335 (10)	0.0287 (9)	0.0301 (9)	0.0009 (7)	0.0037 (7)	−0.0008 (7)
N4	0.0378 (12)	0.0467 (13)	0.0584 (13)	−0.0004 (10)	0.0176 (10)	0.0119 (10)
C1	0.0249 (10)	0.0370 (12)	0.0303 (10)	−0.0031 (9)	0.0062 (8)	−0.0001 (8)
C2	0.0258 (11)	0.0456 (13)	0.0349 (11)	0.0023 (10)	0.0072 (9)	−0.0033 (9)
C3	0.0300 (11)	0.0374 (12)	0.0350 (11)	0.0081 (9)	0.0028 (9)	−0.0063 (9)
C4	0.0276 (10)	0.0310 (11)	0.0280 (10)	0.0024 (9)	0.0005 (8)	−0.0026 (8)
C5	0.0228 (10)	0.0291 (10)	0.0212 (9)	0.0005 (8)	0.0003 (7)	0.0004 (7)
C6	0.0357 (12)	0.0273 (10)	0.0426 (12)	0.0040 (9)	−0.0015 (10)	−0.0033 (9)
C7	0.0301 (10)	0.0301 (11)	0.0362 (10)	0.0012 (9)	0.0056 (8)	−0.0025 (9)
C8	0.0328 (11)	0.0385 (13)	0.0376 (11)	0.0045 (9)	−0.0036 (9)	−0.0069 (9)
C9	0.0421 (13)	0.0401 (12)	0.0277 (10)	0.0082 (10)	−0.0003 (9)	−0.0025 (9)
C10	0.0375 (12)	0.0310 (11)	0.0296 (10)	0.0072 (9)	0.0075 (9)	0.0009 (8)
C11	0.0309 (11)	0.0251 (10)	0.0289 (10)	0.0064 (8)	0.0060 (8)	−0.0004 (8)
C12	0.0419 (13)	0.0388 (12)	0.0359 (11)	0.0064 (10)	0.0016 (10)	0.0008 (10)
C13	0.0431 (14)	0.0496 (15)	0.0482 (14)	0.0159 (12)	0.0001 (11)	0.0026 (11)
C14	0.0449 (14)	0.0441 (14)	0.0507 (14)	0.0121 (11)	0.0094 (11)	−0.0046 (11)
C15	0.0360 (12)	0.0329 (11)	0.0385 (11)	0.0006 (9)	0.0113 (9)	−0.0033 (9)
C16	0.0336 (11)	0.0250 (10)	0.0300 (10)	−0.0042 (9)	0.0069 (8)	−0.0010 (8)
C17	0.0452 (14)	0.0401 (13)	0.0380 (12)	0.0003 (11)	0.0140 (10)	−0.0091 (10)
C18	0.0489 (14)	0.0429 (13)	0.0296 (11)	−0.0077 (11)	0.0087 (10)	−0.0074 (9)
C19	0.0349 (12)	0.0381 (14)	0.0459 (12)	−0.0118 (10)	0.0008 (10)	0.0060 (10)
C20	0.0477 (13)	0.0425 (15)	0.0396 (12)	−0.0123 (11)	−0.0020 (10)	−0.0029 (10)
C21	0.0477 (14)	0.0370 (13)	0.0434 (12)	−0.0045 (10)	0.0099 (10)	−0.0019 (10)
C22	0.0357 (12)	0.0329 (11)	0.0337 (10)	0.0022 (10)	0.0030 (9)	−0.0007 (9)
C23	0.0410 (12)	0.0284 (11)	0.0269 (10)	0.0014 (10)	0.0005 (9)	0.0011 (8)
O1W	0.0885 (14)	0.0585 (12)	0.0549 (10)	0.0020 (10)	0.0246 (10)	0.0019 (9)

Geometric parameters (Å, º)

Zn1—N1	2.1478 (16)	C7—C8	1.399 (3)
Zn1—N1^i	2.1478 (16)	C7—H7A	0.950
Zn1—N3^i	2.1572 (16)	C8—C9	1.362 (3)
Zn1—N3	2.1572 (16)	C8—H8A	0.950
Zn1—N2^i	2.1683 (15)	C9—C10	1.404 (3)
Zn1—N2	2.1683 (15)	C9—H9A	0.950
O1—C19	1.200 (2)	C10—C11	1.407 (2)
O2—C19	1.312 (2)	C10—C18^i	1.433 (3)
O2—H2	0.8201	C11—C16^i	1.443 (3)
O3—C23	1.311 (2)	C12—C13	1.396 (3)
O3—H3	0.8199	C12—H12A	0.950
O4—C23	1.226 (2)	C13—C14	1.361 (3)
O5—N4	1.211 (2)	C13—H13A	0.950
O6A—N4	1.245 (3)	C14—C15	1.402 (3)
O7A—N4	1.228 (3)	C14—H14A	0.950
O6B—N4	1.224 (12)	C15—C16	1.401 (3)
O7B—N4	1.249 (4)	C15—C17	1.433 (3)
N1—C1	1.334 (2)	C16—C11^i	1.443 (3)
N1—C5	1.358 (2)	C17—C18	1.347 (3)
N2—C7	1.320 (2)	C17—H17A	0.950
N2—C11	1.357 (2)	C18—C10^i	1.433 (3)
N3—C12	1.327 (3)	C18—H18A	0.950
N3—C16	1.363 (2)	C19—C20	1.494 (3)
C1—C2	1.384 (3)	C20—C21	1.530 (3)
C1—H1A	0.950	C20—H20A	0.990
C2—C3	1.370 (3)	C20—H20B	0.990
C2—H2A	0.950	C21—C22	1.512 (3)
C3—C4	1.407 (3)	C21—H21A	0.990
C3—H3A	0.950	C21—H21B	0.990
C4—C5	1.398 (3)	C22—C23	1.495 (3)
C4—C6	1.433 (3)	C22—H22A	0.990
C5—C5^i	1.443 (3)	C22—H22B	0.990
C6—C6^i	1.340 (4)	O1W—H1W1	0.8201
C6—H6A	0.950	O1W—H1W2	0.820
N1—Zn1—N1^i	77.90 (8)	C9—C8—H8A	120.7
N1—Zn1—N3^i	93.11 (6)	C7—C8—H8A	120.7
N1^i—Zn1—N3^i	167.83 (6)	C8—C9—C10	120.18 (18)
N1—Zn1—N3	167.83 (6)	C8—C9—H9A	119.9
N1^i—Zn1—N3	93.10 (6)	C10—C9—H9A	119.9
N3^i—Zn1—N3	96.90 (9)	C9—C10—C11	116.99 (18)
N1—Zn1—N2^i	94.85 (6)	C9—C10—C18^i	124.09 (18)
N1^i—Zn1—N2^i	93.73 (5)	C11—C10—C18^i	118.92 (19)
N3^i—Zn1—N2^i	95.20 (6)	N2—C11—C10	122.74 (18)
N3—Zn1—N2^i	77.40 (6)	N2—C11—C16^i	117.95 (16)
N1—Zn1—N2	93.73 (5)	C10—C11—C16^i	119.31 (18)
N1^i—Zn1—N2	94.85 (6)	N3—C12—C13	123.3 (2)
N3^i—Zn1—N2	77.40 (6)	N3—C12—H12A	118.4
N3—Zn1—N2	95.20 (6)	C13—C12—H12A	118.4
N2^i—Zn1—N2	168.96 (8)	C14—C13—C12	118.9 (2)
C19—O2—H2	112.4	C14—C13—H13A	120.6
C23—O3—H3	113.0	C12—C13—H13A	120.6
C1—N1—C5	117.52 (17)	C13—C14—C15	120.0 (2)
C1—N1—Zn1	128.96 (14)	C13—C14—H14A	120.0
C5—N1—Zn1	113.46 (12)	C15—C14—H14A	120.0
C7—N2—C11	118.03 (16)	C16—C15—C14	117.49 (19)
C7—N2—Zn1	128.57 (13)	C16—C15—C17	119.07 (19)
C11—N2—Zn1	113.25 (12)	C14—C15—C17	123.4 (2)
C12—N3—C16	117.87 (17)	N3—C16—C15	122.53 (18)
C12—N3—Zn1	128.31 (14)	N3—C16—C11^i	117.32 (17)
C16—N3—Zn1	113.73 (13)	C15—C16—C11^i	120.15 (17)
O5—N4—O6B	135.1 (6)	C18—C17—C15	120.9 (2)
O5—N4—O7A	118.6 (2)	C18—C17—H17A	119.6
O6B—N4—O7A	94.1 (5)	C15—C17—H17A	119.6
O5—N4—O6A	120.5 (2)	C17—C18—C10^i	121.66 (19)
O6B—N4—O6A	31.5 (4)	C17—C18—H18A	119.2
O7A—N4—O6A	119.7 (2)	C10^i—C18—H18A	119.2
O5—N4—O7B	114.4 (5)	O1—C19—O2	123.2 (2)
O6B—N4—O7B	104.9 (7)	O1—C19—C20	125.4 (2)
O7A—N4—O7B	69.9 (5)	O2—C19—C20	111.34 (18)
O6A—N4—O7B	95.6 (5)	C19—C20—C21	114.84 (18)
N1—C1—C2	123.51 (19)	C19—C20—H20A	108.6
N1—C1—H1A	118.2	C21—C20—H20A	108.6
C2—C1—H1A	118.2	C19—C20—H20B	108.6
C3—C2—C1	119.11 (19)	C21—C20—H20B	108.6
C3—C2—H2A	120.4	H20A—C20—H20B	107.5
C1—C2—H2A	120.4	C22—C21—C20	112.34 (19)
C2—C3—C4	119.45 (19)	C22—C21—H21A	109.1
C2—C3—H3A	120.3	C20—C21—H21A	109.1
C4—C3—H3A	120.3	C22—C21—H21B	109.1
C5—C4—C3	117.46 (18)	C20—C21—H21B	109.1
C5—C4—C6	119.24 (17)	H21A—C21—H21B	107.9
C3—C4—C6	123.29 (18)	C23—C22—C21	113.90 (18)
N1—C5—C4	122.93 (16)	C23—C22—H22A	108.8
N1—C5—C5^i	117.52 (10)	C21—C22—H22A	108.8
C4—C5—C5^i	119.54 (11)	C23—C22—H22B	108.8
C6^i—C6—C4	121.16 (11)	C21—C22—H22B	108.8
C6^i—C6—H6A	119.4	H22A—C22—H22B	107.7
C4—C6—H6A	119.4	O4—C23—O3	122.8 (2)
N2—C7—C8	123.41 (19)	O4—C23—C22	123.34 (18)
N2—C7—H7A	118.3	O3—C23—C22	113.85 (18)
C8—C7—H7A	118.3	H1W1—O1W—H1W2	103.8
C9—C8—C7	118.65 (19)
N1^i—Zn1—N1—C1	−178.27 (19)	C3—C4—C5—C5^i	−179.6 (2)
N3^i—Zn1—N1—C1	−6.54 (16)	C6—C4—C5—C5^i	1.8 (3)
N3—Zn1—N1—C1	138.8 (3)	C5—C4—C6—C6^i	1.3 (3)
N2^i—Zn1—N1—C1	88.95 (16)	C3—C4—C6—C6^i	−177.2 (2)
N2—Zn1—N1—C1	−84.10 (16)	C11—N2—C7—C8	0.5 (3)
N1^i—Zn1—N1—C5	−1.19 (9)	Zn1—N2—C7—C8	175.80 (14)
N3^i—Zn1—N1—C5	170.53 (12)	N2—C7—C8—C9	−0.6 (3)
N3—Zn1—N1—C5	−44.2 (3)	C7—C8—C9—C10	0.2 (3)
N2^i—Zn1—N1—C5	−93.97 (12)	C8—C9—C10—C11	0.3 (3)
N2—Zn1—N1—C5	92.98 (12)	C8—C9—C10—C18^i	179.45 (19)
N1—Zn1—N2—C7	−88.13 (16)	C7—N2—C11—C10	0.1 (3)
N1^i—Zn1—N2—C7	−9.98 (16)	Zn1—N2—C11—C10	−175.94 (14)
N3^i—Zn1—N2—C7	179.52 (17)	C7—N2—C11—C16^i	−179.63 (17)
N3—Zn1—N2—C7	83.59 (16)	Zn1—N2—C11—C16^i	4.3 (2)
N2^i—Zn1—N2—C7	130.91 (16)	C9—C10—C11—N2	−0.5 (3)
N1—Zn1—N2—C11	87.38 (13)	C18^i—C10—C11—N2	−179.65 (18)
N1^i—Zn1—N2—C11	165.53 (12)	C9—C10—C11—C16^i	179.22 (18)
N3^i—Zn1—N2—C11	−4.98 (12)	C18^i—C10—C11—C16^i	0.1 (3)
N3—Zn1—N2—C11	−100.90 (13)	C16—N3—C12—C13	−0.6 (3)
N2^i—Zn1—N2—C11	−53.58 (12)	Zn1—N3—C12—C13	−176.91 (16)
N1—Zn1—N3—C12	130.2 (3)	N3—C12—C13—C14	0.7 (4)
N1^i—Zn1—N3—C12	88.35 (18)	C12—C13—C14—C15	0.0 (4)
N3^i—Zn1—N3—C12	−84.70 (17)	C13—C14—C15—C16	−0.7 (3)
N2^i—Zn1—N3—C12	−178.52 (19)	C13—C14—C15—C17	−179.9 (2)
N2—Zn1—N3—C12	−6.81 (18)	C12—N3—C16—C15	−0.2 (3)
N1—Zn1—N3—C16	−46.2 (4)	Zn1—N3—C16—C15	176.64 (15)
N1^i—Zn1—N3—C16	−88.11 (13)	C12—N3—C16—C11^i	178.68 (18)
N3^i—Zn1—N3—C16	98.84 (14)	Zn1—N3—C16—C11^i	−4.5 (2)
N2^i—Zn1—N3—C16	5.02 (13)	C14—C15—C16—N3	0.8 (3)
N2—Zn1—N3—C16	176.73 (13)	C17—C15—C16—N3	−179.94 (18)
C5—N1—C1—C2	−1.3 (3)	C14—C15—C16—C11^i	−178.03 (19)
Zn1—N1—C1—C2	175.70 (14)	C17—C15—C16—C11^i	1.2 (3)
N1—C1—C2—C3	1.2 (3)	C16—C15—C17—C18	−1.0 (3)
C1—C2—C3—C4	0.1 (3)	C14—C15—C17—C18	178.2 (2)
C2—C3—C4—C5	−1.2 (3)	C15—C17—C18—C10^i	0.3 (3)
C2—C3—C4—C6	177.41 (19)	O1—C19—C20—C21	−14.5 (3)
C1—N1—C5—C4	0.1 (3)	O2—C19—C20—C21	166.71 (19)
Zn1—N1—C5—C4	−177.34 (14)	C19—C20—C21—C22	−77.7 (2)
C1—N1—C5—C5^i	−179.20 (19)	C20—C21—C22—C23	178.96 (17)
Zn1—N1—C5—C5^i	3.4 (2)	C21—C22—C23—O4	9.3 (3)
C3—C4—C5—N1	1.1 (3)	C21—C22—C23—O3	−171.69 (18)
C6—C4—C5—N1	−177.53 (17)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1W	0.82	1.80	2.598 (2)	166
O3—H3···O4^ii	0.82	1.84	2.649 (2)	171
O1W—H1W1···O6B^iii	0.82	2.04	2.774 (11)	149
O1W—H1W1···O7A^iii	0.82	2.09	2.869 (3)	160
O1W—H1W2···O6A	0.82	2.00	2.795 (3)	163
O1W—H1W2···O6B	0.82	2.13	2.952 (11)	175
O1W—H1W2···O7B	0.82	2.17	2.776 (9)	131

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