Bis[1,3-dihydr­oxy-2-hydroxy­methyl-2-(5-nitro-2-oxidobenzylideneamino)propane-κ³N,O,O′]zinc(II) pyridine solvate

The Zn^II atom in the title complex, [Zn(C₁₁H₁₃N₂O₆)₂]·C₅H₅N, is chelated by a terdentate Schiff base ligand in a slightly distorted octa­hedral geometry. One of the coordinated hydroxyl groups forms a hydrogen bond with the pyridine solvent mol­ecule. In the crystal structure, other hydroxyl groups are engaged in inter­molecular hydrogen bonding, forming a two-dimensional layer.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.089
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.85 Ratio

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.716     0.895
            Tmin(prime) and Tmax expected:      0.801     0.892
            RR(prime) =      0.892
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O10     ..       5.63 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT417_ALERT_2_C Short Inter D-H..H-D       H5O    ..  H6O     ..       2.12 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXL97.

Bis[1,3-dihydroxy-2-hydroxymethyl-2-(5-nitrosalicylidimino)propane- κ³N,O,O']zinc(II) pyridine solvate

Crystal data

[Zn(C11H13N2O6)2]·C5H5N	F(000) = 1416
Mr = 682.94	Dx = 1.612 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7842 reflections
a = 11.3298 (2) Å	θ = 2.6–34.4°
b = 11.4928 (2) Å	µ = 0.95 mm^−1
c = 22.0450 (3) Å	T = 173 K
β = 101.348 (1)°	Prism, pale yellow
V = 2814.39 (8) Å^3	0.23 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	6431 independent reflections
Radiation source: fine-focus sealed tube	5457 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.716, Tmax = 0.895	k = −14→14
41884 measured reflections	l = −28→28

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 1.1321P] where P = (Fo^2 + 2Fc^2)/3
6431 reflections	(Δ/σ)max = 0.001
430 parameters	Δρmax = 0.61 e Å^−3
6 restraints	Δρmin = −0.51 e Å^−3

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

	x	y	z	Uiso*/Ueq
Zn1	0.224938 (17)	0.563924 (17)	0.757171 (9)	0.00967 (7)
O1	0.17684 (11)	0.47608 (11)	0.67577 (6)	0.0129 (3)
O2	0.30081 (15)	0.50015 (17)	0.41272 (7)	0.0370 (4)
O3	0.44486 (13)	0.60633 (13)	0.46361 (6)	0.0218 (3)
O4	0.30528 (12)	0.67474 (13)	0.83382 (6)	0.0184 (3)
H4O	0.296 (3)	0.686 (3)	0.8705 (7)	0.063 (10)*
O5	0.61112 (12)	0.48835 (13)	0.79873 (7)	0.0216 (3)
H5O	0.5689 (19)	0.4289 (14)	0.7860 (11)	0.023 (6)*
O6	0.53710 (12)	0.81316 (12)	0.72227 (6)	0.0176 (3)
H6O	0.5987 (18)	0.847 (2)	0.7147 (14)	0.054 (9)*
O7	0.27461 (11)	0.41377 (11)	0.80716 (6)	0.0120 (2)
O8	0.26529 (13)	0.28051 (12)	1.07971 (6)	0.0219 (3)
O9	0.11117 (14)	0.39513 (15)	1.06069 (7)	0.0284 (3)
O10	0.12320 (11)	0.71433 (11)	0.71071 (6)	0.0139 (3)
H10O	0.130 (3)	0.7819 (13)	0.7257 (12)	0.042 (8)*
O11	−0.01979 (12)	0.79243 (11)	0.81296 (7)	0.0182 (3)
H11O	−0.060 (2)	0.8502 (15)	0.8206 (11)	0.030 (7)*
O12	−0.16925 (12)	0.44864 (11)	0.76774 (7)	0.0171 (3)
H12O	−0.2331 (17)	0.475 (3)	0.7770 (14)	0.049 (9)*
N1	0.35432 (16)	0.54583 (15)	0.46088 (7)	0.0204 (4)
N2	0.38935 (13)	0.60805 (13)	0.73579 (7)	0.0106 (3)
N3	0.19519 (14)	0.34349 (14)	1.04456 (7)	0.0165 (3)
N4	0.06420 (13)	0.55605 (12)	0.78806 (7)	0.0095 (3)
N5	0.25764 (16)	0.69224 (15)	0.94789 (8)	0.0208 (4)
C1	0.22023 (15)	0.49528 (15)	0.62653 (8)	0.0116 (3)
C2	0.15285 (17)	0.46069 (16)	0.56763 (9)	0.0158 (4)
H2	0.0761	0.4259	0.5655	0.019*
C3	0.19525 (17)	0.47596 (17)	0.51409 (8)	0.0176 (4)
H3	0.1486	0.4517	0.4755	0.021*
C4	0.30752 (17)	0.52748 (17)	0.51680 (8)	0.0159 (4)
C5	0.37634 (17)	0.56252 (16)	0.57241 (8)	0.0144 (4)
H5	0.4528	0.5970	0.5732	0.017*
C6	0.33536 (16)	0.54815 (15)	0.62763 (8)	0.0121 (3)
C7	0.41581 (15)	0.59311 (15)	0.68249 (8)	0.0119 (3)
H7	0.4952	0.6131	0.6783	0.014*
C8	0.47923 (15)	0.65980 (16)	0.78701 (8)	0.0123 (3)
C9	0.40766 (16)	0.73738 (16)	0.82365 (8)	0.0150 (4)
H9A	0.4588	0.7594	0.8638	0.018*
H9B	0.3819	0.8094	0.8001	0.018*
C10	0.53951 (16)	0.56101 (16)	0.82917 (8)	0.0159 (4)
H10A	0.5908	0.5950	0.8665	0.019*
H10B	0.4766	0.5134	0.8427	0.019*
C11	0.58072 (16)	0.72831 (17)	0.76789 (8)	0.0150 (4)
H11A	0.6286	0.7673	0.8047	0.018*
H11B	0.6346	0.6740	0.7515	0.018*
C12	0.25181 (15)	0.39631 (15)	0.86205 (8)	0.0105 (3)
C13	0.32892 (16)	0.32337 (16)	0.90465 (8)	0.0157 (4)
H13	0.3953	0.2868	0.8920	0.019*
C14	0.31042 (16)	0.30428 (16)	0.96341 (9)	0.0162 (4)
H14	0.3632	0.2555	0.9912	0.019*
C15	0.21225 (16)	0.35803 (16)	0.98162 (8)	0.0135 (3)
C16	0.13258 (15)	0.42636 (15)	0.94146 (8)	0.0117 (3)
H16	0.0653	0.4598	0.9547	0.014*
C17	0.15016 (15)	0.44668 (15)	0.88141 (8)	0.0101 (3)
C18	0.05786 (15)	0.51701 (15)	0.84175 (8)	0.0105 (3)
H18	−0.0126	0.5351	0.8572	0.013*
C19	−0.04186 (14)	0.61642 (15)	0.75141 (8)	0.0101 (3)
C20	−0.00018 (16)	0.67869 (17)	0.69677 (8)	0.0152 (4)
H20A	−0.0122	0.6256	0.6607	0.018*
H20B	−0.0514	0.7480	0.6849	0.018*
C21	−0.10182 (15)	0.70329 (15)	0.78799 (8)	0.0124 (3)
H21A	−0.1726	0.7382	0.7605	0.015*
H21B	−0.1302	0.6624	0.8220	0.015*
C22	−0.13429 (16)	0.52315 (17)	0.72273 (8)	0.0147 (4)
H22A	−0.2067	0.5623	0.6991	0.018*
H22B	−0.0992	0.4754	0.6933	0.018*
C23	0.15253 (19)	0.73148 (18)	0.95805 (9)	0.0221 (4)
H23	0.0958	0.7616	0.9241	0.027*
C24	0.1226 (2)	0.7302 (2)	1.01605 (11)	0.0288 (5)
H24	0.0470	0.7594	1.0216	0.035*
C25	0.2032 (2)	0.6865 (2)	1.06509 (10)	0.0339 (6)
H25	0.1847	0.6846	1.1053	0.041*
C26	0.3122 (2)	0.6450 (2)	1.05509 (11)	0.0331 (5)
H26	0.3700	0.6140	1.0883	0.040*
C27	0.3355 (2)	0.64936 (19)	0.99612 (10)	0.0265 (5)
H27	0.4105	0.6205	0.9895	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.00782 (11)	0.01178 (11)	0.01014 (11)	−0.00032 (7)	0.00352 (7)	0.00023 (7)
O1	0.0124 (6)	0.0141 (6)	0.0131 (6)	−0.0029 (5)	0.0045 (5)	−0.0012 (5)
O2	0.0430 (10)	0.0570 (12)	0.0115 (7)	−0.0081 (9)	0.0065 (7)	−0.0078 (7)
O3	0.0250 (7)	0.0247 (7)	0.0183 (7)	0.0058 (6)	0.0110 (6)	0.0061 (6)
O4	0.0171 (6)	0.0250 (7)	0.0160 (7)	−0.0090 (6)	0.0102 (5)	−0.0083 (6)
O5	0.0127 (6)	0.0187 (7)	0.0340 (8)	0.0012 (6)	0.0065 (6)	0.0008 (6)
O6	0.0131 (6)	0.0180 (7)	0.0229 (7)	−0.0033 (5)	0.0065 (5)	0.0058 (6)
O7	0.0114 (6)	0.0138 (6)	0.0121 (6)	0.0023 (5)	0.0055 (5)	0.0012 (5)
O8	0.0271 (7)	0.0233 (7)	0.0129 (6)	−0.0009 (6)	−0.0020 (5)	0.0060 (6)
O9	0.0282 (8)	0.0438 (9)	0.0162 (7)	0.0092 (7)	0.0120 (6)	0.0046 (7)
O10	0.0131 (6)	0.0130 (6)	0.0171 (6)	−0.0003 (5)	0.0067 (5)	0.0008 (5)
O11	0.0130 (6)	0.0122 (6)	0.0286 (7)	0.0006 (5)	0.0023 (5)	−0.0052 (6)
O12	0.0117 (6)	0.0135 (7)	0.0270 (7)	−0.0008 (5)	0.0060 (5)	0.0010 (5)
N1	0.0262 (9)	0.0239 (9)	0.0118 (8)	0.0071 (7)	0.0055 (6)	0.0016 (6)
N2	0.0093 (7)	0.0118 (7)	0.0106 (7)	0.0005 (6)	0.0018 (5)	−0.0001 (6)
N3	0.0189 (8)	0.0185 (8)	0.0115 (7)	−0.0048 (6)	0.0020 (6)	0.0014 (6)
N4	0.0086 (7)	0.0091 (7)	0.0110 (7)	0.0007 (5)	0.0023 (5)	0.0005 (5)
N5	0.0265 (9)	0.0199 (8)	0.0172 (8)	−0.0085 (7)	0.0073 (7)	−0.0045 (7)
C1	0.0137 (8)	0.0087 (8)	0.0126 (8)	0.0026 (7)	0.0030 (6)	0.0007 (6)
C2	0.0148 (9)	0.0154 (9)	0.0163 (9)	−0.0013 (7)	0.0007 (7)	−0.0013 (7)
C3	0.0212 (9)	0.0180 (9)	0.0117 (8)	0.0025 (8)	−0.0018 (7)	−0.0012 (7)
C4	0.0206 (9)	0.0171 (9)	0.0108 (8)	0.0051 (7)	0.0051 (7)	0.0007 (7)
C5	0.0143 (8)	0.0148 (9)	0.0148 (9)	0.0016 (7)	0.0046 (7)	0.0004 (7)
C6	0.0136 (8)	0.0123 (8)	0.0113 (8)	0.0010 (6)	0.0041 (6)	−0.0005 (6)
C7	0.0094 (8)	0.0130 (8)	0.0138 (8)	−0.0008 (6)	0.0033 (6)	0.0001 (7)
C8	0.0099 (8)	0.0148 (9)	0.0120 (8)	−0.0028 (7)	0.0019 (6)	−0.0012 (7)
C9	0.0140 (8)	0.0162 (9)	0.0163 (9)	−0.0041 (7)	0.0060 (7)	−0.0037 (7)
C10	0.0134 (8)	0.0191 (9)	0.0141 (8)	−0.0012 (7)	0.0000 (7)	0.0009 (7)
C11	0.0103 (8)	0.0184 (9)	0.0164 (9)	−0.0025 (7)	0.0030 (7)	0.0010 (7)
C12	0.0096 (8)	0.0097 (8)	0.0124 (8)	−0.0017 (6)	0.0027 (6)	−0.0010 (6)
C13	0.0132 (8)	0.0174 (9)	0.0171 (9)	0.0058 (7)	0.0043 (7)	0.0032 (7)
C14	0.0151 (9)	0.0162 (9)	0.0165 (9)	0.0025 (7)	0.0011 (7)	0.0041 (7)
C15	0.0142 (8)	0.0159 (9)	0.0106 (8)	−0.0027 (7)	0.0029 (6)	0.0014 (7)
C16	0.0111 (8)	0.0128 (8)	0.0116 (8)	−0.0010 (6)	0.0037 (6)	−0.0006 (6)
C17	0.0090 (7)	0.0108 (8)	0.0107 (8)	−0.0009 (6)	0.0021 (6)	−0.0008 (6)
C18	0.0087 (7)	0.0109 (8)	0.0124 (8)	−0.0004 (6)	0.0037 (6)	−0.0018 (6)
C19	0.0075 (7)	0.0115 (8)	0.0113 (8)	0.0011 (6)	0.0017 (6)	0.0025 (6)
C20	0.0109 (8)	0.0211 (9)	0.0141 (8)	0.0032 (7)	0.0036 (7)	0.0058 (7)
C21	0.0098 (8)	0.0120 (8)	0.0157 (8)	0.0014 (6)	0.0036 (6)	0.0011 (7)
C22	0.0117 (8)	0.0159 (9)	0.0156 (9)	0.0008 (7)	0.0004 (7)	−0.0006 (7)
C23	0.0248 (10)	0.0203 (10)	0.0207 (10)	−0.0064 (8)	0.0029 (8)	−0.0017 (8)
C24	0.0293 (11)	0.0257 (11)	0.0351 (12)	−0.0096 (9)	0.0153 (9)	−0.0101 (9)
C25	0.0555 (16)	0.0319 (12)	0.0177 (10)	−0.0190 (11)	0.0153 (10)	−0.0054 (9)
C26	0.0459 (14)	0.0264 (12)	0.0227 (11)	−0.0056 (10)	−0.0041 (10)	0.0070 (9)
C27	0.0261 (11)	0.0220 (10)	0.0307 (11)	−0.0022 (9)	0.0038 (9)	−0.0024 (9)

Geometric parameters (Å, º)

Zn1—O1	2.037 (1)	C6—C7	1.458 (2)
Zn1—O4	2.168 (1)	C7—H7	0.9500
Zn1—O7	2.065 (1)	C8—C11	1.520 (2)
Zn1—O10	2.214 (1)	C8—C9	1.537 (2)
Zn1—N2	2.072 (2)	C8—C10	1.539 (2)
Zn1—N4	2.068 (2)	C9—H9A	0.9900
O1—C1	1.296 (2)	C9—H9B	0.9900
O2—N1	1.232 (2)	C10—H10A	0.9900
O3—N1	1.231 (2)	C10—H10B	0.9900
O4—C9	1.420 (2)	C11—H11A	0.9900
O4—H4O	0.846 (10)	C11—H11B	0.9900
O5—C10	1.421 (2)	C12—C13	1.423 (2)
O5—H5O	0.850 (10)	C12—C17	1.427 (2)
O6—C11	1.418 (2)	C13—C14	1.370 (3)
O6—H6O	0.845 (10)	C13—H13	0.9500
O7—C12	1.302 (2)	C14—C15	1.398 (3)
O8—N3	1.230 (2)	C14—H14	0.9500
O9—N3	1.232 (2)	C15—C16	1.379 (2)
O10—C20	1.431 (2)	C16—C17	1.397 (2)
O10—H10O	0.842 (10)	C16—H16	0.9500
O11—C21	1.420 (2)	C17—C18	1.467 (2)
O11—H11O	0.838 (10)	C18—H18	0.9500
O12—C22	1.425 (2)	C19—C21	1.525 (2)
O12—H12O	0.847 (10)	C19—C22	1.544 (2)
N1—C4	1.450 (2)	C19—C20	1.552 (2)
N2—C7	1.280 (2)	C20—H20A	0.9900
N2—C8	1.488 (2)	C20—H20B	0.9900
N3—C15	1.448 (2)	C21—H21A	0.9900
N4—C18	1.281 (2)	C21—H21B	0.9900
N4—C19	1.482 (2)	C22—H22A	0.9900
N5—C23	1.333 (3)	C22—H22B	0.9900
N5—C27	1.335 (3)	C23—C24	1.386 (3)
C1—C2	1.427 (2)	C23—H23	0.9500
C1—C6	1.435 (2)	C24—C25	1.367 (3)
C2—C3	1.370 (3)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.381 (4)
C3—C4	1.394 (3)	C25—H25	0.9500
C3—H3	0.9500	C26—C27	1.377 (3)
C4—C5	1.377 (3)	C26—H26	0.9500
C5—C6	1.395 (2)	C27—H27	0.9500
C5—H5	0.9500
O1—Zn1—O7	93.06 (5)	O5—C10—C8	112.02 (15)
O1—Zn1—O4	167.42 (5)	O5—C10—H10A	109.2
O1—Zn1—O10	87.41 (5)	C8—C10—H10A	109.2
O1—Zn1—N2	91.01 (5)	O5—C10—H10B	109.2
O1—Zn1—N4	99.68 (5)	C8—C10—H10B	109.2
O4—Zn1—O7	92.66 (5)	H10A—C10—H10B	107.9
O4—Zn1—O10	90.14 (5)	O6—C11—C8	112.07 (14)
O4—Zn1—N2	77.00 (5)	O6—C11—H11A	109.2
O4—Zn1—N4	91.77 (5)	C8—C11—H11A	109.2
O7—Zn1—O10	164.10 (5)	O6—C11—H11B	109.2
O7—Zn1—N2	99.39 (5)	C8—C11—H11B	109.2
O7—Zn1—N4	87.30 (5)	H11A—C11—H11B	107.9
O10—Zn1—N2	96.50 (5)	O7—C12—C13	119.73 (16)
O10—Zn1—N4	76.97 (5)	O7—C12—C17	122.34 (15)
N2—Zn1—N4	167.11 (6)	C13—C12—C17	117.92 (16)
C1—O1—Zn1	125.01 (11)	C14—C13—C12	122.01 (17)
C9—O4—Zn1	113.92 (10)	C14—C13—H13	119.0
C9—O4—H4O	110 (2)	C12—C13—H13	119.0
Zn1—O4—H4O	136 (2)	C13—C14—C15	118.62 (17)
C10—O5—H5O	107.0 (17)	C13—C14—H14	120.7
C11—O6—H6O	106 (2)	C15—C14—H14	120.7
C12—O7—Zn1	122.80 (11)	C16—C15—C14	121.64 (16)
C20—O10—Zn1	105.87 (10)	C16—C15—N3	119.15 (16)
C20—O10—H10O	111 (2)	C14—C15—N3	119.20 (16)
Zn1—O10—H10O	123 (2)	C15—C16—C17	120.43 (16)
C21—O11—H11O	108.2 (18)	C15—C16—H16	119.8
C22—O12—H12O	109 (2)	C17—C16—H16	119.8
O3—N1—O2	123.17 (17)	C16—C17—C12	119.32 (16)
O3—N1—C4	118.76 (16)	C16—C17—C18	116.06 (15)
O2—N1—C4	118.07 (17)	C12—C17—C18	124.59 (15)
C7—N2—C8	120.09 (15)	N4—C18—C17	125.51 (16)
C7—N2—Zn1	124.00 (12)	N4—C18—H18	117.2
C8—N2—Zn1	115.91 (11)	C17—C18—H18	117.2
O8—N3—O9	122.77 (16)	N4—C19—C21	114.59 (14)
O8—N3—C15	118.70 (16)	N4—C19—C22	108.06 (14)
O9—N3—C15	118.52 (15)	C21—C19—C22	109.53 (14)
C18—N4—C19	118.74 (14)	N4—C19—C20	107.52 (13)
C18—N4—Zn1	122.19 (12)	C21—C19—C20	110.11 (14)
C19—N4—Zn1	118.17 (11)	C22—C19—C20	106.72 (14)
C23—N5—C27	117.59 (18)	O10—C20—C19	113.51 (14)
O1—C1—C2	119.45 (16)	O10—C20—H20A	108.9
O1—C1—C6	123.47 (16)	C19—C20—H20A	108.9
C2—C1—C6	117.07 (16)	O10—C20—H20B	108.9
C3—C2—C1	122.17 (17)	C19—C20—H20B	108.9
C3—C2—H2	118.9	H20A—C20—H20B	107.7
C1—C2—H2	118.9	O11—C21—C19	110.60 (14)
C2—C3—C4	119.29 (17)	O11—C21—H21A	109.5
C2—C3—H3	120.4	C19—C21—H21A	109.5
C4—C3—H3	120.4	O11—C21—H21B	109.5
C5—C4—C3	120.96 (17)	C19—C21—H21B	109.5
C5—C4—N1	118.46 (17)	H21A—C21—H21B	108.1
C3—C4—N1	120.58 (17)	O12—C22—C19	113.02 (14)
C4—C5—C6	120.98 (17)	O12—C22—H22A	109.0
C4—C5—H5	119.5	C19—C22—H22A	109.0
C6—C5—H5	119.5	O12—C22—H22B	109.0
C5—C6—C1	119.53 (16)	C19—C22—H22B	109.0
C5—C6—C7	114.88 (16)	H22A—C22—H22B	107.8
C1—C6—C7	125.57 (16)	N5—C23—C24	122.7 (2)
N2—C7—C6	126.00 (16)	N5—C23—H23	118.6
N2—C7—H7	117.0	C24—C23—H23	118.6
C6—C7—H7	117.0	C25—C24—C23	119.1 (2)
N2—C8—C11	116.03 (14)	C25—C24—H24	120.4
N2—C8—C9	106.12 (14)	C23—C24—H24	120.4
C11—C8—C9	110.57 (15)	C24—C25—C26	118.7 (2)
N2—C8—C10	108.63 (14)	C24—C25—H25	120.6
C11—C8—C10	106.23 (14)	C26—C25—H25	120.6
C9—C8—C10	109.14 (15)	C27—C26—C25	118.8 (2)
O4—C9—C8	108.71 (15)	C27—C26—H26	120.6
O4—C9—H9A	109.9	C25—C26—H26	120.6
C8—C9—H9A	109.9	N5—C27—C26	123.1 (2)
O4—C9—H9B	109.9	N5—C27—H27	118.5
C8—C9—H9B	109.9	C26—C27—H27	118.5
H9A—C9—H9B	108.3
O7—Zn1—O1—C1	−123.40 (14)	C1—C6—C7—N2	−11.0 (3)
N4—Zn1—O1—C1	148.82 (13)	C7—N2—C8—C11	19.8 (2)
N2—Zn1—O1—C1	−23.94 (14)	Zn1—N2—C8—C11	−160.30 (12)
O4—Zn1—O1—C1	−6.4 (3)	C7—N2—C8—C9	143.02 (17)
O10—Zn1—O1—C1	72.51 (13)	Zn1—N2—C8—C9	−37.06 (17)
O1—Zn1—O4—C9	−4.9 (3)	C7—N2—C8—C10	−99.75 (19)
O7—Zn1—O4—C9	112.12 (12)	Zn1—N2—C8—C10	80.17 (15)
N4—Zn1—O4—C9	−160.50 (13)	Zn1—O4—C9—C8	−36.46 (17)
N2—Zn1—O4—C9	13.09 (12)	N2—C8—C9—O4	46.16 (18)
O10—Zn1—O4—C9	−83.54 (12)	C11—C8—C9—O4	172.76 (14)
O1—Zn1—O7—C12	−140.30 (13)	C10—C8—C9—O4	−70.73 (18)
N4—Zn1—O7—C12	−40.75 (13)	N2—C8—C10—O5	66.95 (18)
N2—Zn1—O7—C12	128.17 (13)	C11—C8—C10—O5	−58.53 (19)
O4—Zn1—O7—C12	50.91 (13)	C9—C8—C10—O5	−177.76 (14)
O10—Zn1—O7—C12	−49.0 (2)	N2—C8—C11—O6	51.4 (2)
O1—Zn1—O10—C20	65.45 (11)	C9—C8—C11—O6	−69.45 (19)
O7—Zn1—O10—C20	−26.6 (2)	C10—C8—C11—O6	172.26 (14)
N4—Zn1—O10—C20	−35.11 (11)	Zn1—O7—C12—C13	−151.78 (13)
N2—Zn1—O10—C20	156.17 (11)	Zn1—O7—C12—C17	29.1 (2)
O4—Zn1—O10—C20	−126.89 (11)	O7—C12—C13—C14	178.52 (17)
O1—Zn1—N2—C7	10.74 (15)	C17—C12—C13—C14	−2.4 (3)
O7—Zn1—N2—C7	104.01 (15)	C12—C13—C14—C15	0.3 (3)
N4—Zn1—N2—C7	−135.4 (2)	C13—C14—C15—C16	1.9 (3)
O4—Zn1—N2—C7	−165.41 (16)	C13—C14—C15—N3	−176.83 (17)
O10—Zn1—N2—C7	−76.77 (15)	O8—N3—C15—C16	178.57 (16)
O1—Zn1—N2—C8	−169.18 (12)	O9—N3—C15—C16	−1.7 (3)
O7—Zn1—N2—C8	−75.90 (12)	O8—N3—C15—C14	−2.7 (3)
N4—Zn1—N2—C8	44.7 (3)	O9—N3—C15—C14	177.10 (18)
O4—Zn1—N2—C8	14.68 (12)	C14—C15—C16—C17	−1.9 (3)
O10—Zn1—N2—C8	103.32 (12)	N3—C15—C16—C17	176.81 (16)
O1—Zn1—N4—C18	126.54 (14)	C15—C16—C17—C12	−0.2 (3)
O7—Zn1—N4—C18	33.89 (14)	C15—C16—C17—C18	177.85 (16)
N2—Zn1—N4—C18	−87.8 (3)	O7—C12—C17—C16	−178.60 (16)
O4—Zn1—N4—C18	−58.70 (14)	C13—C12—C17—C16	2.3 (2)
O10—Zn1—N4—C18	−148.43 (14)	O7—C12—C17—C18	3.5 (3)
O1—Zn1—N4—C19	−64.42 (12)	C13—C12—C17—C18	−175.62 (16)
O7—Zn1—N4—C19	−157.07 (12)	C19—N4—C18—C17	174.29 (15)
N2—Zn1—N4—C19	81.2 (3)	Zn1—N4—C18—C17	−16.7 (2)
O4—Zn1—N4—C19	110.35 (12)	C16—C17—C18—N4	171.71 (17)
O10—Zn1—N4—C19	20.61 (11)	C12—C17—C18—N4	−10.3 (3)
Zn1—O1—C1—C2	−157.67 (13)	C18—N4—C19—C21	44.2 (2)
Zn1—O1—C1—C6	23.7 (2)	Zn1—N4—C19—C21	−125.20 (13)
O1—C1—C2—C3	−178.32 (17)	C18—N4—C19—C22	−78.18 (19)
C6—C1—C2—C3	0.4 (3)	Zn1—N4—C19—C22	112.40 (13)
C1—C2—C3—C4	−0.4 (3)	C18—N4—C19—C20	166.98 (15)
C2—C3—C4—C5	0.3 (3)	Zn1—N4—C19—C20	−2.45 (17)
C2—C3—C4—N1	−179.40 (17)	Zn1—O10—C20—C19	45.53 (16)
O3—N1—C4—C5	−10.2 (3)	N4—C19—C20—O10	−30.1 (2)
O2—N1—C4—C5	170.06 (18)	C21—C19—C20—O10	95.34 (17)
O3—N1—C4—C3	169.53 (17)	C22—C19—C20—O10	−145.87 (15)
O2—N1—C4—C3	−10.2 (3)	N4—C19—C21—O11	60.53 (19)
C3—C4—C5—C6	−0.4 (3)	C22—C19—C21—O11	−177.87 (14)
N1—C4—C5—C6	179.34 (16)	C20—C19—C21—O11	−60.82 (18)
C4—C5—C6—C1	0.5 (3)	N4—C19—C22—O12	57.07 (19)
C4—C5—C6—C7	−177.87 (17)	C21—C19—C22—O12	−68.39 (18)
O1—C1—C6—C5	178.22 (16)	C20—C19—C22—O12	172.45 (14)
C2—C1—C6—C5	−0.5 (2)	C27—N5—C23—C24	0.6 (3)
O1—C1—C6—C7	−3.6 (3)	N5—C23—C24—C25	−0.4 (3)
C2—C1—C6—C7	177.68 (17)	C23—C24—C25—C26	0.1 (3)
C8—N2—C7—C6	−177.28 (16)	C24—C25—C26—C27	0.0 (3)
Zn1—N2—C7—C6	2.8 (3)	C23—N5—C27—C26	−0.5 (3)
C5—C6—C7—N2	167.24 (18)	C25—C26—C27—N5	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···N5	0.85 (1)	1.84 (1)	2.681 (2)	171 (3)
O4—H4o···N5	0.85 (1)	1.84 (1)	2.681 (2)	171 (3)
O5—H5o···O6^i	0.85 (1)	1.78 (1)	2.604 (2)	164 (2)
O6—H6o···O7^ii	0.85 (1)	1.77 (1)	2.618 (2)	175 (3)
O10—H10o···O12^iii	0.84 (1)	1.97 (1)	2.766 (2)	158 (3)
O11—H11o···O1^iii	0.84 (1)	1.98 (1)	2.803 (2)	169 (2)
O12—H12o···O5^iv	0.85 (1)	1.92 (1)	2.745 (2)	163 (3)

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