Bis[(1H-benzimidazol-2-yl)methanol-κ²N,O](nitrato-κ²O,O′)zinc(II) nitrate monohydrate

The title compound, [Zn(NO₃)(C₈H₈N₂O)₂]NO₃·H₂O, consists of a tris-chelated zinc cation and a nitrate anion, along with an uncoordinated water mol­ecule. These inter­act through O—H...O and N—H...O hydrogen bonds, giving rise to a three-dimensional network structure. The Zn^II ion has an octa­hedral coordination.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.114
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O1   -H1O     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.850(10) ......       5.00 su-Ra
              O1   -H1O     1.555   1.555
PLAT736_ALERT_1_B H...A   Calc     1.80(5), Rep   1.800(10) ......       5.00 su-Ra
              H1O  -O1W     1.555   1.555

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    -   O4      ..       7.75 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N2   -H2N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N4   -H4N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Ra
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N2   -H2N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              N4   -H4N     1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

  14 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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[(1H-benzimidazol-2-yl)methanol-κ²N,O](nitrato-κ²O,O')zinc(II) nitrate monohydrate

Crystal data

[Zn(NO3)(C8H8N2O)2]NO3·H2O	Z = 2
Mr = 503.73	F(000) = 516
Triclinic, P1	Dx = 1.683 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2287 (8) Å	Cell parameters from 1775 reflections
b = 9.6745 (9) Å	θ = 2.6–25.3°
c = 13.542 (1) Å	µ = 1.30 mm^−1
α = 81.506 (2)°	T = 293 K
β = 80.678 (2)°	Plate, pale yellow
γ = 69.867 (2)°	0.20 × 0.15 × 0.08 mm
V = 993.89 (15) Å^3

Data collection

Bruker APEX2 area-detector diffractometer	3444 independent reflections
Radiation source: fine-focus sealed tube	2947 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.781, Tmax = 0.903	k = −7→11
5025 measured reflections	l = −14→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.1377P] where P = (Fo^2 + 2Fc^2)/3
3444 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.42 e Å^−3
6 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq
Zn1	0.63068 (5)	0.28762 (4)	0.71867 (3)	0.03887 (16)
O1	0.7129 (4)	0.4602 (3)	0.61315 (18)	0.0498 (6)
O2	0.8274 (4)	0.1249 (3)	0.80316 (19)	0.0552 (7)
O3	0.3507 (3)	0.3877 (3)	0.70619 (18)	0.0528 (6)
O4	0.4400 (4)	0.1801 (3)	0.7952 (2)	0.0597 (7)
O5	0.1635 (4)	0.2852 (4)	0.7842 (2)	0.0794 (9)
O6	1.0456 (4)	0.1810 (3)	0.23550 (19)	0.0685 (8)
O7	0.9411 (4)	0.3797 (3)	0.1372 (2)	0.0639 (8)
O8	1.0147 (4)	0.1678 (3)	0.0834 (2)	0.0733 (9)
O1w	0.9389 (4)	0.5498 (4)	0.6807 (2)	0.0660 (8)
N1	0.7096 (3)	0.1969 (3)	0.58860 (18)	0.0362 (6)
N2	0.8324 (4)	0.1899 (3)	0.4307 (2)	0.0428 (7)
N3	0.6455 (3)	0.3992 (3)	0.82755 (18)	0.0364 (6)
N4	0.7730 (4)	0.4208 (3)	0.9528 (2)	0.0436 (7)
N5	0.3140 (4)	0.2837 (4)	0.7627 (2)	0.0518 (8)
N6	0.9990 (4)	0.2446 (4)	0.1516 (2)	0.0480 (7)
C1	0.7183 (4)	0.0643 (4)	0.5560 (2)	0.0366 (7)
C2	0.6608 (4)	−0.0497 (4)	0.6050 (3)	0.0428 (8)
H2	0.6090	−0.0474	0.6714	0.051*
C3	0.6835 (5)	−0.1657 (4)	0.5515 (3)	0.0504 (9)
H3	0.6439	−0.2427	0.5821	0.060*
C4	0.7641 (5)	−0.1721 (4)	0.4527 (3)	0.0531 (9)
H4	0.7782	−0.2538	0.4195	0.064*
C5	0.8235 (5)	−0.0603 (4)	0.4030 (3)	0.0482 (9)
H5	0.8783	−0.0647	0.3373	0.058*
C6	0.7972 (4)	0.0583 (4)	0.4562 (2)	0.0395 (8)
C7	0.7782 (4)	0.2673 (4)	0.5116 (2)	0.0378 (7)
C8	0.7888 (5)	0.4168 (4)	0.5156 (3)	0.0496 (9)
H8A	0.9094	0.4138	0.5039	0.059*
H8B	0.7258	0.4867	0.4645	0.059*
C9	0.5821 (4)	0.5475 (4)	0.8472 (2)	0.0377 (7)
C10	0.4643 (5)	0.6696 (4)	0.8017 (3)	0.0469 (9)
H10	0.4082	0.6612	0.7496	0.056*
C11	0.4330 (5)	0.8044 (4)	0.8362 (3)	0.0564 (10)
H11	0.3544	0.8886	0.8068	0.068*
C12	0.5167 (6)	0.8169 (4)	0.9142 (3)	0.0610 (11)
H12	0.4936	0.9100	0.9349	0.073*
C13	0.6315 (5)	0.6975 (4)	0.9613 (3)	0.0539 (10)
H13	0.6855	0.7069	1.0140	0.065*
C14	0.6637 (4)	0.5609 (4)	0.9267 (2)	0.0417 (8)
C15	0.7580 (4)	0.3290 (4)	0.8921 (2)	0.0389 (7)
C16	0.8541 (5)	0.1691 (4)	0.8933 (2)	0.0460 (8)
H16A	0.9773	0.1497	0.8955	0.055*
H16B	0.8101	0.1154	0.9517	0.055*
H1O	0.782 (5)	0.485 (6)	0.641 (4)	0.11 (2)*
H2O	0.855 (5)	0.0325 (12)	0.808 (3)	0.056 (12)*
H1W1	0.996 (6)	0.478 (4)	0.719 (3)	0.084 (17)*
H1W2	0.900 (6)	0.628 (3)	0.711 (3)	0.090 (19)*
H2N	0.881 (6)	0.218 (5)	0.3748 (19)	0.088 (16)*
H4N	0.837 (4)	0.393 (4)	1.0003 (19)	0.048 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0469 (3)	0.0401 (3)	0.0314 (2)	−0.01608 (18)	−0.00224 (16)	−0.00750 (16)
O1	0.0711 (18)	0.0497 (15)	0.0372 (13)	−0.0326 (13)	0.0014 (12)	−0.0081 (11)
O2	0.0726 (18)	0.0408 (16)	0.0455 (14)	−0.0046 (13)	−0.0153 (12)	−0.0089 (12)
O3	0.0508 (15)	0.0615 (17)	0.0481 (15)	−0.0217 (13)	−0.0064 (11)	−0.0033 (13)
O4	0.0673 (18)	0.0543 (17)	0.0574 (16)	−0.0234 (14)	−0.0033 (13)	−0.0012 (13)
O5	0.0532 (18)	0.113 (3)	0.083 (2)	−0.0460 (17)	0.0105 (15)	−0.0174 (19)
O6	0.0733 (19)	0.079 (2)	0.0406 (15)	−0.0107 (16)	−0.0144 (13)	0.0078 (14)
O7	0.078 (2)	0.0454 (17)	0.0676 (18)	−0.0107 (14)	−0.0248 (15)	−0.0090 (14)
O8	0.104 (2)	0.0565 (18)	0.0601 (18)	−0.0157 (16)	−0.0254 (17)	−0.0171 (15)
O1w	0.0637 (19)	0.085 (3)	0.0547 (18)	−0.0283 (18)	−0.0079 (15)	−0.0131 (18)
N1	0.0441 (15)	0.0366 (15)	0.0299 (13)	−0.0161 (12)	−0.0013 (11)	−0.0057 (11)
N2	0.0512 (18)	0.0500 (18)	0.0290 (15)	−0.0216 (14)	0.0009 (13)	−0.0033 (13)
N3	0.0436 (15)	0.0380 (15)	0.0290 (13)	−0.0160 (12)	−0.0034 (11)	−0.0030 (11)
N4	0.0504 (17)	0.0532 (19)	0.0312 (15)	−0.0209 (14)	−0.0100 (13)	−0.0013 (13)
N5	0.054 (2)	0.062 (2)	0.0448 (17)	−0.0233 (17)	0.0010 (15)	−0.0197 (16)
N6	0.0477 (17)	0.053 (2)	0.0403 (17)	−0.0136 (15)	−0.0065 (13)	−0.0022 (15)
C1	0.0376 (17)	0.0366 (18)	0.0356 (17)	−0.0096 (14)	−0.0075 (13)	−0.0066 (14)
C2	0.0439 (19)	0.042 (2)	0.0408 (18)	−0.0151 (15)	−0.0015 (15)	−0.0013 (15)
C3	0.057 (2)	0.039 (2)	0.058 (2)	−0.0174 (17)	−0.0152 (18)	−0.0019 (17)
C4	0.058 (2)	0.043 (2)	0.061 (2)	−0.0108 (18)	−0.0139 (19)	−0.0199 (18)
C5	0.049 (2)	0.056 (2)	0.0390 (18)	−0.0114 (17)	−0.0059 (15)	−0.0164 (17)
C6	0.0374 (18)	0.047 (2)	0.0337 (17)	−0.0108 (15)	−0.0065 (14)	−0.0079 (15)
C7	0.0428 (18)	0.0443 (19)	0.0296 (16)	−0.0183 (15)	−0.0035 (13)	−0.0045 (14)
C8	0.071 (2)	0.046 (2)	0.0370 (18)	−0.0307 (18)	−0.0024 (17)	0.0018 (15)
C9	0.0439 (18)	0.0379 (18)	0.0303 (16)	−0.0157 (15)	0.0028 (13)	−0.0030 (13)
C10	0.054 (2)	0.045 (2)	0.0394 (19)	−0.0154 (17)	−0.0022 (16)	−0.0023 (16)
C11	0.065 (3)	0.039 (2)	0.055 (2)	−0.0111 (18)	0.0071 (19)	−0.0027 (17)
C12	0.078 (3)	0.044 (2)	0.061 (2)	−0.025 (2)	0.014 (2)	−0.0158 (19)
C13	0.071 (3)	0.062 (3)	0.0393 (19)	−0.036 (2)	0.0031 (18)	−0.0140 (18)
C14	0.049 (2)	0.046 (2)	0.0330 (17)	−0.0224 (16)	0.0010 (14)	−0.0049 (15)
C15	0.0434 (19)	0.044 (2)	0.0297 (16)	−0.0176 (15)	−0.0012 (14)	−0.0016 (14)
C16	0.052 (2)	0.047 (2)	0.0350 (18)	−0.0115 (16)	−0.0077 (15)	0.0005 (15)

Geometric parameters (Å, º)

Zn1—O1	2.246 (3)	N4—H4N	0.85 (1)
Zn1—O2	2.173 (3)	C1—C2	1.386 (5)
Zn1—O3	2.195 (2)	C1—C6	1.403 (4)
Zn1—O4	2.213 (3)	C2—C3	1.368 (5)
Zn1—N1	1.997 (2)	C2—H2	0.93
Zn1—N3	1.993 (3)	C3—C4	1.394 (5)
O1—C8	1.424 (4)	C3—H3	0.93
O1—H1O	0.85 (1)	C4—C5	1.380 (5)
O2—C16	1.424 (4)	C4—H4	0.93
O2—H2O	0.84 (1)	C5—C6	1.380 (5)
O3—N5	1.263 (4)	C5—H5	0.93
O4—N5	1.255 (4)	C7—C8	1.489 (5)
O5—N5	1.221 (4)	C8—H8A	0.97
O6—N6	1.261 (4)	C8—H8B	0.97
O7—N6	1.224 (4)	C9—C10	1.380 (5)
O8—N6	1.233 (4)	C9—C14	1.401 (5)
O1w—H1W1	0.85 (1)	C10—C11	1.376 (5)
O1w—H1W2	0.85 (1)	C10—H10	0.93
N1—C7	1.316 (4)	C11—C12	1.392 (6)
N1—C1	1.393 (4)	C11—H11	0.93
N2—C7	1.346 (4)	C12—C13	1.363 (6)
N2—C6	1.385 (5)	C12—H12	0.93
N2—H2N	0.85 (1)	C13—C14	1.392 (5)
N3—C15	1.318 (4)	C13—H13	0.93
N3—C9	1.398 (4)	C15—C16	1.474 (5)
N4—C15	1.343 (4)	C16—H16A	0.97
N4—C14	1.376 (4)	C16—H16B	0.97
O1—Zn1—O2	117.3 (1)	C2—C3—C4	122.1 (4)
O1—Zn1—O3	96.2 (1)	C2—C3—H3	119.0
O1—Zn1—O4	154.1 (1)	C4—C3—H3	119.0
O1—Zn1—N1	76.2 (1)	C5—C4—C3	121.6 (3)
O1—Zn1—N3	85.3 (1)	C5—C4—H4	119.2
O2—Zn1—O3	145.4 (1)	C3—C4—H4	119.2
O2—Zn1—O4	88.6 (1)	C4—C5—C6	116.4 (3)
O2—Zn1—N1	96.7 (1)	C4—C5—H5	121.8
O2—Zn1—N3	77.1 (1)	C6—C5—H5	121.8
O3—Zn1—O4	58.1 (1)	C5—C6—N2	132.6 (3)
O3—Zn1—N1	99.5 (1)	C5—C6—C1	122.2 (3)
O3—Zn1—N3	98.8 (1)	N2—C6—C1	105.2 (3)
O4—Zn1—N1	103.1 (1)	N1—C7—N2	112.3 (3)
O4—Zn1—N3	100.8 (1)	N1—C7—C8	122.5 (3)
N1—Zn1—N3	155.2 (1)	N2—C7—C8	125.2 (3)
C8—O1—Zn1	114.9 (2)	O1—C8—C7	107.1 (3)
C8—O1—H1O	110 (4)	O1—C8—H8A	110.3
Zn1—O1—H1O	108 (4)	C7—C8—H8A	110.3
C16—O2—Zn1	115.8 (2)	O1—C8—H8B	110.3
C16—O2—H2O	110 (3)	C7—C8—H8B	110.3
Zn1—O2—H2O	128 (3)	H8A—C8—H8B	108.5
N5—O3—Zn1	93.0 (2)	C10—C9—N3	131.3 (3)
N5—O4—Zn1	92.4 (2)	C10—C9—C14	120.8 (3)
H1W1—O1w—H1W2	110 (5)	N3—C9—C14	107.9 (3)
C7—N1—C1	106.0 (3)	C11—C10—C9	117.5 (3)
C7—N1—Zn1	119.0 (2)	C11—C10—H10	121.2
C1—N1—Zn1	134.9 (2)	C9—C10—H10	121.2
C7—N2—C6	107.8 (3)	C10—C11—C12	121.2 (4)
C7—N2—H2N	125 (3)	C10—C11—H11	119.4
C6—N2—H2N	127 (3)	C12—C11—H11	119.4
C15—N3—C9	106.4 (3)	C13—C12—C11	122.3 (4)
C15—N3—Zn1	117.5 (2)	C13—C12—H12	118.8
C9—N3—Zn1	135.2 (2)	C11—C12—H12	118.8
C15—N4—C14	108.2 (3)	C12—C13—C14	116.7 (4)
C15—N4—H4N	124 (2)	C12—C13—H13	121.6
C14—N4—H4N	128 (2)	C14—C13—H13	121.6
O5—N5—O4	122.3 (4)	N4—C14—C13	132.9 (3)
O5—N5—O3	121.3 (4)	N4—C14—C9	105.7 (3)
O4—N5—O3	116.5 (3)	C13—C14—C9	121.4 (3)
O7—N6—O8	120.4 (3)	N3—C15—N4	111.8 (3)
O7—N6—O6	121.1 (3)	N3—C15—C16	122.1 (3)
O8—N6—O6	118.5 (3)	N4—C15—C16	126.1 (3)
C2—C1—N1	130.7 (3)	O2—C16—C15	106.3 (3)
C2—C1—C6	120.6 (3)	O2—C16—H16A	110.5
N1—C1—C6	108.7 (3)	C15—C16—H16A	110.5
C3—C2—C1	117.1 (3)	O2—C16—H16B	110.5
C3—C2—H2	121.4	C15—C16—H16B	110.5
C1—C2—H2	121.4	H16A—C16—H16B	108.7
N3—Zn1—O1—C8	158.5 (3)	N1—C1—C2—C3	178.0 (3)
N1—Zn1—O1—C8	−4.8 (2)	C6—C1—C2—C3	−0.4 (5)
O2—Zn1—O1—C8	85.7 (3)	C1—C2—C3—C4	1.4 (5)
O3—Zn1—O1—C8	−103.1 (2)	C2—C3—C4—C5	−0.9 (6)
O4—Zn1—O1—C8	−96.4 (3)	C3—C4—C5—C6	−0.6 (5)
N3—Zn1—O2—C16	6.1 (2)	C4—C5—C6—N2	−177.4 (3)
N1—Zn1—O2—C16	161.7 (2)	C4—C5—C6—C1	1.5 (5)
O3—Zn1—O2—C16	−80.7 (3)	C7—N2—C6—C5	179.5 (3)
O4—Zn1—O2—C16	−95.3 (2)	C7—N2—C6—C1	0.4 (4)
O1—Zn1—O2—C16	83.8 (3)	C2—C1—C6—C5	−1.0 (5)
N3—Zn1—O3—N5	−96.53 (19)	N1—C1—C6—C5	−179.8 (3)
N1—Zn1—O3—N5	100.28 (19)	C2—C1—C6—N2	178.1 (3)
O2—Zn1—O3—N5	−16.6 (3)	N1—C1—C6—N2	−0.6 (4)
O4—Zn1—O3—N5	0.76 (18)	C1—N1—C7—N2	−0.3 (4)
O1—Zn1—O3—N5	177.30 (18)	Zn1—N1—C7—N2	177.2 (2)
N3—Zn1—O4—N5	93.0 (2)	C1—N1—C7—C8	178.4 (3)
N1—Zn1—O4—N5	−94.0 (2)	Zn1—N1—C7—C8	−4.1 (4)
O2—Zn1—O4—N5	169.5 (2)	C6—N2—C7—N1	−0.1 (4)
O3—Zn1—O4—N5	−0.76 (18)	C6—N2—C7—C8	−178.7 (3)
O1—Zn1—O4—N5	−8.7 (3)	Zn1—O1—C8—C7	4.0 (4)
N3—Zn1—N1—C7	−38.4 (4)	N1—C7—C8—O1	−0.3 (5)
O2—Zn1—N1—C7	−111.9 (2)	N2—C7—C8—O1	178.2 (3)
O3—Zn1—N1—C7	98.7 (2)	C15—N3—C9—C10	178.9 (3)
O4—Zn1—N1—C7	158.0 (2)	Zn1—N3—C9—C10	9.7 (5)
O1—Zn1—N1—C7	4.6 (2)	C15—N3—C9—C14	0.1 (3)
N3—Zn1—N1—C1	138.2 (3)	Zn1—N3—C9—C14	−169.1 (2)
O2—Zn1—N1—C1	64.7 (3)	N3—C9—C10—C11	−177.5 (3)
O3—Zn1—N1—C1	−84.7 (3)	C14—C9—C10—C11	1.1 (5)
O4—Zn1—N1—C1	−25.4 (3)	C9—C10—C11—C12	−0.1 (5)
O1—Zn1—N1—C1	−178.8 (3)	C10—C11—C12—C13	−0.9 (6)
N1—Zn1—N3—C15	−77.0 (3)	C11—C12—C13—C14	0.9 (6)
O2—Zn1—N3—C15	0.8 (2)	C15—N4—C14—C13	−177.4 (4)
O3—Zn1—N3—C15	145.8 (2)	C15—N4—C14—C9	0.2 (4)
O4—Zn1—N3—C15	86.8 (2)	C12—C13—C14—N4	177.4 (4)
O1—Zn1—N3—C15	−118.6 (2)	C12—C13—C14—C9	0.1 (5)
N1—Zn1—N3—C9	91.3 (4)	C10—C9—C14—N4	−179.1 (3)
O2—Zn1—N3—C9	169.1 (3)	N3—C9—C14—N4	−0.2 (4)
O3—Zn1—N3—C9	−45.9 (3)	C10—C9—C14—C13	−1.1 (5)
O4—Zn1—N3—C9	−104.9 (3)	N3—C9—C14—C13	177.8 (3)
O1—Zn1—N3—C9	49.6 (3)	C9—N3—C15—N4	0.0 (4)
Zn1—O4—N5—O5	−178.5 (3)	Zn1—N3—C15—N4	171.4 (2)
Zn1—O4—N5—O3	1.3 (3)	C9—N3—C15—C16	−179.2 (3)
Zn1—O3—N5—O5	178.5 (3)	Zn1—N3—C15—C16	−7.8 (4)
Zn1—O3—N5—O4	−1.3 (3)	C14—N4—C15—N3	−0.1 (4)
C7—N1—C1—C2	−178.0 (3)	C14—N4—C15—C16	179.1 (3)
Zn1—N1—C1—C2	5.1 (5)	Zn1—O2—C16—C15	−10.5 (3)
C7—N1—C1—C6	0.6 (3)	N3—C15—C16—O2	12.1 (4)
Zn1—N1—C1—C6	−176.3 (2)	N4—C15—C16—O2	−167.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1w	0.85 (1)	1.80 (1)	2.635 (4)	172 (5)
O2—H2O···O6^i	0.84 (1)	2.08 (2)	2.877 (4)	159 (4)
O1w—H1w1···O5^ii	0.85 (1)	2.07 (2)	2.908 (5)	168 (5)
O1w—H1w2···O6^iii	0.85 (1)	2.29 (3)	3.038 (5)	148 (5)
N2—H2n···O6	0.85 (1)	2.14 (2)	2.922 (4)	154 (4)
N4—H4n···O7^iv	0.85 (1)	2.14 (2)	2.959 (4)	163 (3)

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