Triaqua­(pyridine-2,5-dicarboxyl­ato-κ²N,O²)[4,4,5,5-tetra­methyl-2-(4-pyrid­yl)imidazoline-1-oxyl-κN²]zinc(II)

The title compound, [Zn(C₇H₃NO₄)(C₁₂H₁₆N₃O)(H₂O)₃], was prepared from the imino nitroxide radical ligand 2-(4-pyrid­yl)-4,4,5,5-tetra­methyl­imidazoline-1-oxyl, zinc(II) perchlorate and potassium pyridine-2,5-dicarboxyl­ate. The Zn^II ion exists in a distorted octa­hedral coordination geometry with one pyridyl N atom from a radical ligand, one N and one O atom from a bidentate pyridine-2,5-dicarboxyl­ate ligand and three O atoms from water mol­ecules. A two-dimensional network is formed through O—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.077
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.69 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.42 Ratio

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.651     0.810
            Tmin(prime) and Tmax expected:      0.734     0.812
            RR(prime) =      0.889
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and PLATON (Spek,2003); software used to prepare material for publication: SHELXTL.

Triaqua(pyridine-2,5-dicarboxylato-κ²N,O²)[4,4,5,5-tetramethyl- 2-(4-pyridyl)imidazoline-1-oxyl-κN²]zinc(II)

Crystal data

[Zn(C7H3NO4)(C12H16N3O)(H2O)3]	F(000) = 1044
Mr = 502.80	Dx = 1.502 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3163 reflections
a = 16.978 (6) Å	θ = 2.3–25.2°
b = 7.355 (3) Å	µ = 1.16 mm^−1
c = 18.812 (7) Å	T = 293 K
β = 108.867 (5)°	Block, red
V = 2222.9 (14) Å^3	0.26 × 0.24 × 0.18 mm
Z = 4

Data collection

Bruker APEX-II CCD area-detector diffractometer	3931 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
Tmin = 0.651, Tmax = 0.810	k = −8→7
11537 measured reflections	l = −22→22

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) = 0.077	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.57P] where P = (Fo^2 + 2Fc^2)/3
3931 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.43 e Å^−3
9 restraints	Δρmin = −0.37 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
Zn1	0.381364 (14)	0.01203 (3)	0.170175 (12)	0.02408 (9)
O1	−0.05234 (12)	0.2683 (3)	−0.00368 (11)	0.0701 (6)
O2	0.36209 (11)	−0.1087 (2)	−0.19566 (8)	0.0401 (4)
O3	0.35158 (12)	−0.3275 (2)	−0.11877 (9)	0.0440 (4)
O4	0.42201 (9)	0.27804 (19)	0.16930 (8)	0.0301 (3)
O5	0.42067 (12)	0.51511 (19)	0.09642 (9)	0.0423 (4)
O6	0.40201 (9)	0.04270 (19)	0.28816 (8)	0.0297 (3)
H6A	0.3750	−0.0256	0.3085	0.045*
H6B	0.4536	0.0527	0.3124	0.045*
O7	0.33877 (9)	−0.25174 (19)	0.16627 (8)	0.0315 (3)
H7A	0.3396	−0.2858	0.2097	0.047*
H7B	0.3643	−0.3209	0.1449	0.047*
O8	0.50193 (9)	−0.0878 (2)	0.19646 (8)	0.0353 (4)
H8A'	0.5193	−0.1280	0.2412	0.053*
H8B'	0.5352	−0.0138	0.1863	0.053*
N1	0.25793 (11)	0.1227 (2)	0.15202 (10)	0.0303 (4)
N2	0.00625 (12)	0.4530 (3)	0.17416 (12)	0.0451 (5)
N3	−0.04992 (12)	0.3363 (3)	0.05891 (11)	0.0428 (5)
N4	0.38121 (10)	0.0475 (2)	0.05452 (9)	0.0227 (4)
C1	0.17435 (14)	0.3651 (3)	0.17320 (13)	0.0366 (5)
H1	0.1717	0.4753	0.1966	0.044*
C2	0.24985 (14)	0.2818 (3)	0.18387 (13)	0.0347 (5)
H2	0.2977	0.3386	0.2147	0.042*
C3	0.18828 (14)	0.0447 (3)	0.10808 (13)	0.0384 (6)
H3	0.1926	−0.0662	0.0859	0.046*
C4	0.11013 (14)	0.1196 (3)	0.09378 (13)	0.0405 (6)
H4	0.0634	0.0611	0.0621	0.049*
C5	0.10241 (14)	0.2835 (3)	0.12739 (12)	0.0333 (5)
C6	0.02052 (14)	0.3628 (3)	0.12108 (13)	0.0364 (5)
C7	−0.12448 (14)	0.3807 (4)	0.08071 (14)	0.0436 (6)
C8	−0.19320 (18)	0.4602 (4)	0.01456 (17)	0.0649 (9)
H8A	−0.1727	0.5658	−0.0038	0.097*
H8B	−0.2396	0.4937	0.0304	0.097*
H8C	−0.2107	0.3712	−0.0248	0.097*
C9	−0.15334 (19)	0.1996 (4)	0.1031 (2)	0.0713 (9)
H9A	−0.1671	0.1179	0.0611	0.107*
H9B	−0.2015	0.2189	0.1183	0.107*
H9C	−0.1095	0.1479	0.1441	0.107*
C10	−0.08339 (16)	0.5082 (4)	0.14713 (16)	0.0500 (7)
C11	−0.1178 (2)	0.4894 (5)	0.2127 (2)	0.0911 (14)
H11A	−0.1142	0.3647	0.2286	0.137*
H11B	−0.1749	0.5276	0.1969	0.137*
H11C	−0.0859	0.5640	0.2538	0.137*
C12	−0.0841 (2)	0.7069 (4)	0.1246 (2)	0.0831 (11)
H12A	−0.0488	0.7757	0.1661	0.125*
H12B	−0.1399	0.7531	0.1110	0.125*
H12C	−0.0641	0.7174	0.0826	0.125*
C13	0.41275 (13)	0.3517 (3)	0.10620 (11)	0.0264 (5)
C14	0.39329 (13)	0.2226 (3)	0.04003 (11)	0.0246 (4)
C15	0.39113 (15)	0.2819 (3)	−0.02962 (12)	0.0354 (5)
H15	0.3982	0.4044	−0.0382	0.043*
C16	0.37819 (15)	0.1561 (3)	−0.08696 (12)	0.0356 (5)
H16	0.3751	0.1938	−0.1350	0.043*
C17	0.36993 (13)	−0.0255 (3)	−0.07248 (11)	0.0260 (5)
C18	0.36019 (13)	−0.1668 (3)	−0.13357 (11)	0.0276 (5)
C19	0.37122 (13)	−0.0738 (3)	−0.00070 (11)	0.0255 (5)
H19	0.3649	−0.1957	0.0094	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03057 (15)	0.02112 (15)	0.02131 (14)	0.00038 (10)	0.00942 (10)	0.00099 (10)
O1	0.0525 (12)	0.0974 (17)	0.0533 (12)	0.0145 (11)	0.0074 (10)	−0.0327 (12)
O2	0.0710 (12)	0.0294 (9)	0.0263 (8)	−0.0069 (8)	0.0245 (8)	−0.0040 (7)
O3	0.0827 (13)	0.0209 (9)	0.0373 (9)	−0.0032 (8)	0.0320 (9)	−0.0029 (7)
O4	0.0444 (9)	0.0237 (8)	0.0222 (7)	−0.0060 (7)	0.0106 (6)	−0.0014 (6)
O5	0.0783 (13)	0.0186 (9)	0.0348 (9)	−0.0024 (8)	0.0251 (9)	−0.0015 (7)
O6	0.0377 (9)	0.0290 (8)	0.0241 (7)	−0.0039 (7)	0.0124 (7)	0.0008 (6)
O7	0.0464 (9)	0.0228 (8)	0.0286 (8)	−0.0004 (7)	0.0166 (7)	0.0013 (6)
O8	0.0354 (9)	0.0433 (10)	0.0287 (8)	0.0056 (7)	0.0123 (7)	0.0109 (7)
N1	0.0307 (10)	0.0280 (10)	0.0311 (9)	0.0016 (8)	0.0086 (8)	−0.0024 (8)
N2	0.0380 (12)	0.0522 (13)	0.0433 (12)	0.0102 (10)	0.0104 (10)	−0.0131 (10)
N3	0.0353 (11)	0.0511 (13)	0.0401 (12)	0.0048 (10)	0.0094 (9)	−0.0146 (10)
N4	0.0311 (9)	0.0188 (9)	0.0194 (8)	0.0003 (7)	0.0097 (7)	0.0003 (7)
C1	0.0369 (13)	0.0319 (13)	0.0415 (13)	0.0026 (10)	0.0134 (11)	−0.0093 (10)
C2	0.0321 (12)	0.0325 (13)	0.0380 (13)	−0.0017 (10)	0.0094 (10)	−0.0082 (10)
C3	0.0386 (13)	0.0332 (13)	0.0426 (14)	0.0021 (10)	0.0121 (11)	−0.0126 (11)
C4	0.0310 (13)	0.0406 (14)	0.0450 (14)	−0.0011 (11)	0.0055 (11)	−0.0128 (11)
C5	0.0327 (12)	0.0335 (13)	0.0330 (12)	0.0026 (10)	0.0095 (10)	−0.0033 (10)
C6	0.0338 (13)	0.0363 (13)	0.0374 (13)	0.0019 (10)	0.0092 (10)	−0.0042 (11)
C7	0.0318 (13)	0.0468 (16)	0.0515 (15)	0.0063 (11)	0.0127 (11)	−0.0055 (13)
C8	0.0447 (17)	0.079 (2)	0.0599 (19)	0.0176 (15)	0.0013 (14)	−0.0133 (16)
C9	0.0529 (19)	0.067 (2)	0.097 (3)	−0.0077 (15)	0.0277 (18)	−0.0010 (19)
C10	0.0374 (14)	0.0571 (18)	0.0540 (16)	0.0117 (12)	0.0127 (13)	−0.0163 (13)
C11	0.065 (2)	0.152 (4)	0.064 (2)	0.017 (2)	0.0323 (18)	−0.030 (2)
C12	0.067 (2)	0.0462 (19)	0.118 (3)	0.0131 (16)	0.005 (2)	−0.0241 (19)
C13	0.0332 (12)	0.0224 (12)	0.0263 (11)	0.0011 (9)	0.0133 (9)	−0.0012 (9)
C14	0.0318 (11)	0.0191 (11)	0.0249 (10)	0.0032 (9)	0.0119 (9)	0.0005 (8)
C15	0.0631 (16)	0.0172 (11)	0.0300 (12)	−0.0004 (10)	0.0207 (11)	0.0027 (9)
C16	0.0615 (16)	0.0258 (13)	0.0251 (11)	0.0006 (11)	0.0217 (11)	0.0018 (9)
C17	0.0343 (12)	0.0215 (11)	0.0242 (10)	0.0009 (9)	0.0121 (9)	−0.0004 (9)
C18	0.0346 (12)	0.0258 (12)	0.0256 (11)	0.0000 (9)	0.0143 (9)	−0.0029 (9)
C19	0.0336 (12)	0.0177 (10)	0.0268 (11)	−0.0009 (9)	0.0120 (9)	0.0005 (9)

Geometric parameters (Å, º)

Zn1—O7	2.0634 (16)	C3—H3	0.9300
Zn1—O4	2.0765 (16)	C4—C5	1.387 (3)
Zn1—O8	2.0782 (16)	C4—H4	0.9300
Zn1—O6	2.1440 (16)	C5—C6	1.476 (3)
Zn1—N1	2.1699 (19)	C7—C8	1.520 (4)
Zn1—N4	2.1904 (18)	C7—C9	1.526 (4)
O1—N3	1.268 (2)	C7—C10	1.537 (4)
O2—C18	1.254 (2)	C8—H8A	0.9600
O3—C18	1.234 (3)	C8—H8B	0.9600
O4—C13	1.268 (2)	C8—H8C	0.9600
O5—C13	1.229 (2)	C9—H9A	0.9600
O6—H6A	0.8501	C9—H9B	0.9600
O6—H6B	0.8500	C9—H9C	0.9600
O7—H7A	0.8502	C10—C12	1.521 (4)
O7—H7B	0.8501	C10—C11	1.533 (4)
O8—H8A'	0.8502	C11—H11A	0.9600
O8—H8B'	0.8500	C11—H11B	0.9600
N1—C3	1.334 (3)	C11—H11C	0.9600
N1—C2	1.342 (3)	C12—H12A	0.9600
N2—C6	1.285 (3)	C12—H12B	0.9600
N2—C10	1.496 (3)	C12—H12C	0.9600
N3—C6	1.390 (3)	C13—C14	1.515 (3)
N3—C7	1.488 (3)	C14—C15	1.370 (3)
N4—C19	1.338 (3)	C15—C16	1.383 (3)
N4—C14	1.346 (3)	C15—H15	0.9300
C1—C2	1.376 (3)	C16—C17	1.379 (3)
C1—C5	1.383 (3)	C16—H16	0.9300
C1—H1	0.9300	C17—C19	1.390 (3)
C2—H2	0.9300	C17—C18	1.519 (3)
C3—C4	1.380 (3)	C19—H19	0.9300
O7—Zn1—O4	177.63 (5)	C8—C7—C9	109.4 (2)
O7—Zn1—O8	89.04 (6)	N3—C7—C10	98.92 (19)
O4—Zn1—O8	91.74 (7)	C8—C7—C10	117.2 (2)
O7—Zn1—O6	94.23 (5)	C9—C7—C10	114.2 (2)
O4—Zn1—O6	88.03 (5)	C7—C8—H8A	109.5
O8—Zn1—O6	88.40 (6)	C7—C8—H8B	109.5
O7—Zn1—N1	92.16 (7)	H8A—C8—H8B	109.5
O4—Zn1—N1	87.23 (7)	C7—C8—H8C	109.5
O8—Zn1—N1	175.44 (6)	H8A—C8—H8C	109.5
O6—Zn1—N1	87.12 (6)	H8B—C8—H8C	109.5
O7—Zn1—N4	100.89 (6)	C7—C9—H9A	109.5
O4—Zn1—N4	76.91 (6)	C7—C9—H9B	109.5
O8—Zn1—N4	87.89 (6)	H9A—C9—H9B	109.5
O6—Zn1—N4	164.36 (6)	C7—C9—H9C	109.5
N1—Zn1—N4	96.20 (6)	H9A—C9—H9C	109.5
C13—O4—Zn1	118.00 (13)	H9B—C9—H9C	109.5
Zn1—O6—H6A	118.1	N2—C10—C12	105.8 (2)
Zn1—O6—H6B	111.0	N2—C10—C11	108.2 (2)
H6A—O6—H6B	115.1	C12—C10—C11	109.9 (3)
Zn1—O7—H7A	110.2	N2—C10—C7	104.78 (19)
Zn1—O7—H7B	110.7	C12—C10—C7	113.5 (2)
H7A—O7—H7B	115.3	C11—C10—C7	114.1 (3)
Zn1—O8—H8A'	111.0	C10—C11—H11A	109.5
Zn1—O8—H8B'	113.3	C10—C11—H11B	109.5
H8A'—O8—H8B'	113.8	H11A—C11—H11B	109.5
C3—N1—C2	116.99 (19)	C10—C11—H11C	109.5
C3—N1—Zn1	123.62 (15)	H11A—C11—H11C	109.5
C2—N1—Zn1	119.34 (14)	H11B—C11—H11C	109.5
C6—N2—C10	107.6 (2)	C10—C12—H12A	109.5
O1—N3—C6	126.7 (2)	C10—C12—H12B	109.5
O1—N3—C7	124.60 (19)	H12A—C12—H12B	109.5
C6—N3—C7	108.34 (19)	C10—C12—H12C	109.5
C19—N4—C14	118.05 (17)	H12A—C12—H12C	109.5
C19—N4—Zn1	130.62 (14)	H12B—C12—H12C	109.5
C14—N4—Zn1	111.34 (12)	O5—C13—O4	124.86 (19)
C2—C1—C5	119.4 (2)	O5—C13—C14	119.67 (18)
C2—C1—H1	120.3	O4—C13—C14	115.43 (18)
C5—C1—H1	120.3	N4—C14—C15	122.64 (18)
N1—C2—C1	123.3 (2)	N4—C14—C13	116.14 (17)
N1—C2—H2	118.4	C15—C14—C13	121.19 (18)
C1—C2—H2	118.4	C14—C15—C16	118.8 (2)
N1—C3—C4	123.6 (2)	C14—C15—H15	120.6
N1—C3—H3	118.2	C16—C15—H15	120.6
C4—C3—H3	118.2	C17—C16—C15	119.60 (19)
C3—C4—C5	119.0 (2)	C17—C16—H16	120.2
C3—C4—H4	120.5	C15—C16—H16	120.2
C5—C4—H4	120.5	C16—C17—C19	117.97 (19)
C1—C5—C4	117.8 (2)	C16—C17—C18	120.43 (18)
C1—C5—C6	119.8 (2)	C19—C17—C18	121.60 (18)
C4—C5—C6	122.1 (2)	O3—C18—O2	125.3 (2)
N2—C6—N3	113.5 (2)	O3—C18—C17	118.48 (18)
N2—C6—C5	123.4 (2)	O2—C18—C17	116.24 (19)
N3—C6—C5	123.0 (2)	N4—C19—C17	122.84 (19)
N3—C7—C8	110.8 (2)	N4—C19—H19	118.6
N3—C7—C9	105.2 (2)	C17—C19—H19	118.6
O8—Zn1—O4—C13	101.38 (15)	O1—N3—C7—C8	−39.2 (4)
O6—Zn1—O4—C13	−170.28 (15)	C6—N3—C7—C8	147.3 (2)
N1—Zn1—O4—C13	−83.07 (15)	O1—N3—C7—C9	78.9 (3)
N4—Zn1—O4—C13	13.95 (15)	C6—N3—C7—C9	−94.6 (2)
O7—Zn1—N1—C3	−35.45 (19)	O1—N3—C7—C10	−162.9 (2)
O4—Zn1—N1—C3	142.25 (19)	C6—N3—C7—C10	23.6 (3)
O6—Zn1—N1—C3	−129.59 (19)	C6—N2—C10—C12	−101.6 (3)
N4—Zn1—N1—C3	65.74 (19)	C6—N2—C10—C11	140.7 (3)
O7—Zn1—N1—C2	147.18 (16)	C6—N2—C10—C7	18.6 (3)
O4—Zn1—N1—C2	−35.11 (16)	N3—C7—C10—N2	−24.7 (3)
O6—Zn1—N1—C2	53.05 (16)	C8—C7—C10—N2	−143.7 (2)
N4—Zn1—N1—C2	−111.62 (17)	C9—C7—C10—N2	86.5 (3)
O7—Zn1—N4—C19	−10.72 (18)	N3—C7—C10—C12	90.2 (3)
O4—Zn1—N4—C19	170.18 (19)	C8—C7—C10—C12	−28.8 (4)
O8—Zn1—N4—C19	77.90 (18)	C9—C7—C10—C12	−158.6 (3)
O6—Zn1—N4—C19	154.3 (2)	N3—C7—C10—C11	−142.8 (2)
N1—Zn1—N4—C19	−104.13 (18)	C8—C7—C10—C11	98.2 (3)
O7—Zn1—N4—C14	169.18 (14)	C9—C7—C10—C11	−31.6 (3)
O4—Zn1—N4—C14	−9.93 (13)	Zn1—O4—C13—O5	167.16 (18)
O8—Zn1—N4—C14	−102.21 (14)	Zn1—O4—C13—C14	−14.9 (2)
O6—Zn1—N4—C14	−25.8 (3)	C19—N4—C14—C15	3.7 (3)
N1—Zn1—N4—C14	75.77 (14)	Zn1—N4—C14—C15	−176.23 (17)
C3—N1—C2—C1	0.0 (3)	C19—N4—C14—C13	−174.17 (18)
Zn1—N1—C2—C1	177.58 (18)	Zn1—N4—C14—C13	5.9 (2)
C5—C1—C2—N1	−0.2 (4)	O5—C13—C14—N4	−176.6 (2)
C2—N1—C3—C4	0.6 (4)	O4—C13—C14—N4	5.3 (3)
Zn1—N1—C3—C4	−176.84 (18)	O5—C13—C14—C15	5.5 (3)
N1—C3—C4—C5	−1.0 (4)	O4—C13—C14—C15	−172.5 (2)
C2—C1—C5—C4	−0.2 (4)	N4—C14—C15—C16	−1.7 (3)
C2—C1—C5—C6	174.4 (2)	C13—C14—C15—C16	176.0 (2)
C3—C4—C5—C1	0.8 (4)	C14—C15—C16—C17	−1.6 (4)
C3—C4—C5—C6	−173.6 (2)	C15—C16—C17—C19	2.9 (3)
C10—N2—C6—N3	−3.3 (3)	C15—C16—C17—C18	−176.8 (2)
C10—N2—C6—C5	−179.2 (2)	C16—C17—C18—O3	−178.8 (2)
O1—N3—C6—N2	172.6 (3)	C19—C17—C18—O3	1.5 (3)
C7—N3—C6—N2	−14.1 (3)	C16—C17—C18—O2	1.6 (3)
O1—N3—C6—C5	−11.5 (4)	C19—C17—C18—O2	−178.1 (2)
C7—N3—C6—C5	161.8 (2)	C14—N4—C19—C17	−2.3 (3)
C1—C5—C6—N2	−29.3 (4)	Zn1—N4—C19—C17	177.58 (15)
C4—C5—C6—N2	145.0 (3)	C16—C17—C19—N4	−0.9 (3)
C1—C5—C6—N3	155.2 (2)	C18—C17—C19—N4	178.77 (18)
C4—C5—C6—N3	−30.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3^i	0.85	1.88	2.697 (3)	160
O6—H6B···O5^ii	0.85	2.28	3.097 (3)	161
O7—H7A···O2^i	0.85	1.87	2.700 (2)	167
O7—H7B···O5^iii	0.85	1.94	2.790 (3)	178
O8—H8A′···O4^ii	0.85	1.79	2.629 (2)	167
O8—H8B′···O2^iv	0.85	1.92	2.728 (3)	159

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