Poly[[aqua­[μ₂-1,3-bis­(pyridin-4-yl)urea-κ²N⁴:N^4′]bis­(μ₃-5-tert-butyl­isophthalato-κ³O¹:O^1′:O³)dizinc(II)] trihydrate], a double-strand coordination polymer

In the title compound, {[Zn₂(C₁₂H₁₂O₄)₂(C₁₁H₁₀N₄O)(H₂O)]·3H₂O}_n, monoperiodic coordination polymer double strands are held into the triperiodic crystal structure by means of N—H...O hydrogen-bonding patterns between the amide groups of the 1,3-di(pyridin-4-yl)urea ligands and unligated O atoms belonging to 5-tert-butyl­isophthalate ligands. One of the Zn atoms displays a tetra­hedral coordination environment, while the other Zn atom adopts a five-coordinate geometry inter­mediate between square pyramidal and trigonal bipyramidal. Additionally, O—H...O hydrogen-bonding patterns involving the water mol­ecules of crystallization serve as a structure-stabilizing element by aggregating the double-strand motifs.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.155
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20      --C21      .       15.5 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20      --C22      .       11.5 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C20      --C23      .        9.0 s.u.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WA     ..H1WA     .       1.99 Ang.
                                                 1-x,-y,1-z  =      2_656 Check
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WA     ..H3WB     .       1.99 Ang.
                                                      x,y,z  =      1_555 Check
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WB     ..H3WB     .       2.00 Ang.
                                                      x,y,z  =      1_555 Check
PLAT420_ALERT_2_B D-H Bond Without Acceptor  O1W      --H1WB     .     Please Check

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.04 Report
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O2W      0.131 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O3W      0.104 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00755 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1WA     ..H1WB     .       2.13 Ang.
                                                 1-x,-y,1-z  =      2_656 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT921_ALERT_1_C R1  in the CIF and FCF Differ by ...............     0.0016 Check
PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ...............     0.0036 Check
PLAT923_ALERT_1_C S    Values in the CIF and FCF Differ by .......      0.026 Check
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  1.06Ang From O9      .       0.41 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.77Ang From O3W     .      -0.42 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.60Ang From O3W     .      -0.41 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............         10 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          3 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          5 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O7         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O7A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O8         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O8A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C31        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C31A       Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         6% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          6 Note
PLAT794_ALERT_5_G Tentative Bond Valency for Zn2       (II)      .       1.96 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          5 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        39% Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.0 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   7 ALERT level B = A potentially serious problem, consider carefully
  13 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  22 ALERT level G = General information/check it is not something unexpected

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT v8.34A (Bruker, 2014); data reduction: SAINT v8.34A (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: CrystalMaker X (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[aqua[µ₂-1,3-bis(pyridin-4-yl)urea-κ²N⁴:N^4']bis(µ₃-5-tert-butylisophthalato-κ³O¹:O^1':O³)dizinc(II)] trihydrate]

Crystal data

[Zn2(C12H12O4)2(C11H10N4O)(H2O)]·3H2O	Z = 2
Mr = 857.46	F(000) = 888
Triclinic, P1	Dx = 1.573 Mg m^−3
a = 10.0232 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9921 (11) Å	Cell parameters from 5602 reflections
c = 17.4698 (17) Å	θ = 2.4–25.3°
α = 100.182 (1)°	µ = 1.40 mm^−1
β = 100.460 (1)°	T = 173 K
γ = 101.335 (1)°	Chunk, colourless
V = 1810.2 (3) Å^3	0.13 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	6575 independent reflections
Radiation source: sealed tube	4380 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
Detector resolution: 8.36 pixels mm^-1	θmax = 25.3°, θmin = 1.2°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
Tmin = 0.696, Tmax = 0.745	l = −20→21
25998 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 1.4791P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6575 reflections	Δρmax = 1.33 e Å^−3
493 parameters	Δρmin = −0.65 e Å^−3
5 restraints

Special details

Experimental. Data were collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using omega scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structure was solved by the direct method using the SHELXT program and refined by least squares method on F2, SHELXL, incorporated in OLEX2.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structure was refined by Least Squares using version 2018/3 of XL (Sheldrick, 2015) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. All H atoms were placed in calculated positions with C—H = 0.98 Å for CH₃ groups and 0.95 Å for phenyl and pyridyl groups, N—H = 0.88 Å, 0.88 Å for the coordinated water ligand and 0.87 Å for solvent water molecules. Hydrogen atoms were constrained to ride on their parent atoms, with U_iso(H) = 1.2 U_eq(C,N) for aromatic hydrogen atoms and N—H groups and with U_iso(H) = 1.2 U_eq(C,O) for methyl groups and all oxygen atoms.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.38132 (6)	0.30660 (6)	0.39727 (3)	0.02965 (19)
Zn2	0.61061 (6)	0.11823 (6)	0.28134 (3)	0.03045 (19)
O1	0.3106 (4)	0.1265 (3)	0.3413 (2)	0.0403 (9)
O2	0.4073 (3)	0.0235 (3)	0.2530 (2)	0.0359 (9)
O3	−0.1993 (3)	0.1023 (3)	0.26575 (19)	0.0326 (8)
O4	−0.3317 (3)	−0.0717 (3)	0.1824 (2)	0.0341 (8)
O5	0.5679 (3)	0.3284 (3)	0.46735 (18)	0.0330 (8)
O6	0.6496 (4)	0.2880 (3)	0.35802 (19)	0.0355 (9)
O7	1.2637 (7)	0.2507 (7)	0.5132 (4)	0.0328 (10)	0.5
O7A	1.2822 (8)	0.3242 (7)	0.4917 (4)	0.0328 (10)	0.5
O8	1.2077 (9)	0.3474 (8)	0.4165 (5)	0.039 (2)	0.5
O8A	1.1426 (8)	0.3094 (8)	0.3755 (5)	0.0328 (10)	0.5
O9	0.3808 (4)	0.5378 (4)	0.0421 (2)	0.0488 (11)
O10	0.6375 (4)	0.0199 (4)	0.3730 (3)	0.0614 (12)
H10A	0.695720	−0.030452	0.364270	0.092*
H10B	0.558890	−0.036272	0.372250	0.092*
N1	0.4125 (4)	0.4238 (4)	0.3209 (2)	0.0308 (10)
N2	0.5062 (4)	0.6579 (4)	0.1645 (2)	0.0343 (10)
H2	0.564503	0.731560	0.187950	0.041*
N3	0.5180 (4)	0.7370 (4)	0.0532 (2)	0.0351 (11)
H3	0.581303	0.798638	0.087919	0.042*
N4	0.4375 (4)	0.8144 (4)	−0.1743 (2)	0.0309 (10)
C1	0.3507 (5)	0.3873 (5)	0.2435 (3)	0.0341 (12)
H1	0.285912	0.306966	0.225244	0.041*
C2	0.3760 (5)	0.4602 (5)	0.1885 (3)	0.0341 (12)
H2A	0.329037	0.430044	0.133989	0.041*
C3	0.4702 (5)	0.5774 (5)	0.2135 (3)	0.0328 (12)
C4	0.5331 (5)	0.6168 (5)	0.2951 (3)	0.0349 (13)
H4	0.596677	0.697517	0.315202	0.042*
C5	0.5028 (5)	0.5386 (5)	0.3456 (3)	0.0338 (12)
H5	0.547361	0.566630	0.400565	0.041*
C6	0.4606 (5)	0.6357 (5)	0.0825 (3)	0.0332 (12)
C7	0.3781 (5)	0.7017 (5)	−0.1630 (3)	0.0359 (13)
H7	0.316776	0.641538	−0.207380	0.043*
C8	0.4006 (6)	0.6666 (5)	−0.0894 (3)	0.0377 (13)
H8	0.356602	0.584512	−0.084316	0.045*
C9	0.4883 (5)	0.7540 (5)	−0.0244 (3)	0.0319 (12)
C10	0.5527 (5)	0.8704 (5)	−0.0363 (3)	0.0338 (12)
H10	0.616375	0.931550	0.006766	0.041*
C11	0.5243 (5)	0.8970 (5)	−0.1101 (3)	0.0352 (13)
H11	0.568231	0.978228	−0.116561	0.042*
C12	0.3050 (5)	0.0536 (5)	0.2759 (3)	0.0270 (11)
C13	0.1629 (5)	−0.0044 (4)	0.2218 (3)	0.0248 (11)
C14	0.1506 (5)	−0.0888 (5)	0.1498 (3)	0.0280 (11)
H14	0.232221	−0.110072	0.136486	0.034*
C15	0.0222 (5)	−0.1428 (4)	0.0969 (3)	0.0257 (11)
C16	−0.0950 (5)	−0.1130 (4)	0.1203 (3)	0.0265 (11)
H16	−0.184452	−0.152363	0.086602	0.032*
C17	−0.0862 (5)	−0.0276 (4)	0.1912 (3)	0.0255 (11)
C18	0.0447 (5)	0.0293 (4)	0.2418 (3)	0.0255 (11)
H18	0.052938	0.090366	0.289325	0.031*
C19	−0.2145 (5)	0.0018 (5)	0.2143 (3)	0.0256 (11)
C20	0.0077 (5)	−0.2321 (5)	0.0162 (3)	0.0375 (13)
C21	0.1438 (8)	−0.2552 (7)	0.0016 (4)	0.0754 (13)
H21A	0.200943	−0.177036	−0.006137	0.113*
H21B	0.126774	−0.322976	−0.046180	0.113*
H21C	0.193123	−0.280747	0.047701	0.113*
C22	−0.0783 (8)	−0.3659 (7)	0.0180 (4)	0.0754 (13)
H22A	−0.025505	−0.400700	0.058277	0.113*
H22B	−0.095853	−0.422886	−0.034495	0.113*
H22C	−0.167438	−0.358048	0.031455	0.113*
C23	−0.0777 (8)	−0.1923 (7)	−0.0508 (4)	0.0754 (13)
H23A	−0.170808	−0.192197	−0.040841	0.113*
H23B	−0.086323	−0.252084	−0.101222	0.113*
H23C	−0.031702	−0.106620	−0.054091	0.113*
C24	0.6671 (5)	0.3144 (4)	0.4332 (3)	0.0273 (11)
C25	0.8089 (5)	0.3317 (4)	0.4840 (3)	0.0272 (11)
C26	0.9219 (5)	0.3176 (4)	0.4499 (3)	0.0298 (12)
H26	0.910061	0.299218	0.393564	0.036*
C27	1.0512 (5)	0.3304 (5)	0.4988 (3)	0.0358 (13)
C28	1.0671 (5)	0.3553 (5)	0.5811 (3)	0.0343 (12)
H28	1.155945	0.361394	0.613817	0.041*
C29	0.9571 (5)	0.3715 (5)	0.6173 (3)	0.0279 (11)
C30	0.8288 (5)	0.3610 (4)	0.5669 (3)	0.0261 (11)
H30	0.752307	0.374166	0.589668	0.031*
C31	1.1850 (15)	0.3084 (12)	0.4767 (7)	0.0328 (10)	0.5
C31A	1.1618 (14)	0.3207 (14)	0.4492 (8)	0.0328 (10)	0.5
C32	0.9775 (6)	0.4005 (5)	0.7085 (3)	0.0369 (13)
C33	0.8481 (6)	0.3313 (6)	0.7321 (3)	0.0513 (16)
H33A	0.767100	0.362334	0.710670	0.077*
H33B	0.863868	0.347516	0.790444	0.077*
H33C	0.830626	0.239633	0.710421	0.077*
C34	0.9951 (7)	0.5441 (6)	0.7375 (4)	0.0598 (18)
H34A	1.079881	0.590080	0.725212	0.090*
H34B	1.002733	0.564110	0.795337	0.090*
H34C	0.913940	0.569712	0.710635	0.090*
C35	1.1038 (7)	0.3611 (7)	0.7494 (4)	0.0589 (18)
H35A	1.091752	0.269102	0.731535	0.088*
H35B	1.113470	0.382567	0.807333	0.088*
H35C	1.187780	0.405971	0.735757	0.088*
O2W	0.8558 (8)	−0.0788 (8)	0.4110 (5)	0.131 (3)
H2WA	0.849857	−0.131613	0.442563	0.196*
H2WB	0.928881	−0.018318	0.435648	0.196*
O3W	0.8410 (7)	0.0382 (6)	0.5714 (4)	0.104 (2)
H3WA	0.790799	−0.021227	0.588147	0.156*
H3WB	0.820815	0.012124	0.519791	0.156*
O1W	0.4387 (6)	−0.1147 (5)	0.4373 (3)	0.0763 (15)
H1WA	0.410888	−0.061226	0.470248	0.114*
H1WB	0.509999	−0.131385	0.466540	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0193 (3)	0.0393 (4)	0.0255 (3)	0.0067 (3)	0.0028 (2)	−0.0030 (3)
Zn2	0.0175 (3)	0.0445 (4)	0.0246 (3)	0.0073 (3)	0.0027 (2)	−0.0023 (3)
O1	0.031 (2)	0.044 (2)	0.033 (2)	0.0044 (17)	0.0022 (17)	−0.0139 (17)
O2	0.0170 (19)	0.053 (2)	0.031 (2)	0.0054 (17)	0.0032 (15)	−0.0033 (17)
O3	0.0206 (19)	0.041 (2)	0.0295 (19)	0.0087 (16)	0.0035 (15)	−0.0086 (16)
O4	0.0195 (19)	0.041 (2)	0.032 (2)	0.0019 (16)	0.0032 (16)	−0.0066 (16)
O5	0.0188 (18)	0.057 (2)	0.0183 (17)	0.0039 (17)	0.0055 (14)	0.0003 (16)
O6	0.044 (2)	0.038 (2)	0.0202 (18)	0.0099 (18)	0.0049 (16)	−0.0021 (15)
O7	0.020 (2)	0.045 (3)	0.031 (2)	0.009 (2)	0.0063 (19)	−0.001 (2)
O7A	0.020 (2)	0.045 (3)	0.031 (2)	0.009 (2)	0.0063 (19)	−0.001 (2)
O8	0.041 (6)	0.040 (5)	0.049 (5)	0.015 (4)	0.031 (4)	0.010 (4)
O8A	0.020 (2)	0.045 (3)	0.031 (2)	0.009 (2)	0.0063 (19)	−0.001 (2)
O9	0.054 (3)	0.047 (2)	0.028 (2)	−0.009 (2)	−0.0043 (19)	0.0015 (18)
O10	0.035 (2)	0.086 (3)	0.072 (3)	0.018 (2)	0.010 (2)	0.037 (3)
N1	0.021 (2)	0.039 (3)	0.031 (2)	0.006 (2)	0.0085 (19)	0.002 (2)
N2	0.032 (3)	0.035 (2)	0.026 (2)	−0.003 (2)	−0.0008 (19)	0.0005 (19)
N3	0.032 (3)	0.037 (3)	0.028 (2)	0.000 (2)	0.001 (2)	−0.001 (2)
N4	0.024 (2)	0.039 (3)	0.026 (2)	0.007 (2)	0.0038 (19)	−0.0009 (19)
C1	0.019 (3)	0.039 (3)	0.037 (3)	0.005 (2)	−0.001 (2)	−0.002 (2)
C2	0.027 (3)	0.041 (3)	0.026 (3)	0.006 (2)	−0.002 (2)	−0.003 (2)
C3	0.021 (3)	0.041 (3)	0.036 (3)	0.007 (2)	0.007 (2)	0.006 (2)
C4	0.023 (3)	0.042 (3)	0.033 (3)	0.002 (2)	0.003 (2)	−0.001 (2)
C5	0.024 (3)	0.043 (3)	0.028 (3)	0.004 (2)	0.002 (2)	−0.001 (2)
C6	0.029 (3)	0.036 (3)	0.031 (3)	0.006 (3)	0.003 (2)	0.004 (2)
C7	0.026 (3)	0.040 (3)	0.030 (3)	0.002 (2)	0.001 (2)	−0.009 (2)
C8	0.029 (3)	0.045 (3)	0.032 (3)	0.004 (3)	0.001 (2)	0.002 (3)
C9	0.025 (3)	0.043 (3)	0.027 (3)	0.012 (2)	0.005 (2)	0.001 (2)
C10	0.028 (3)	0.043 (3)	0.021 (3)	0.005 (2)	−0.002 (2)	−0.007 (2)
C11	0.030 (3)	0.040 (3)	0.027 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
C12	0.019 (3)	0.033 (3)	0.024 (3)	0.004 (2)	0.003 (2)	0.001 (2)
C13	0.025 (3)	0.027 (3)	0.019 (2)	0.003 (2)	0.003 (2)	0.001 (2)
C14	0.021 (3)	0.033 (3)	0.029 (3)	0.008 (2)	0.005 (2)	0.002 (2)
C15	0.023 (3)	0.028 (3)	0.022 (2)	0.003 (2)	0.004 (2)	−0.001 (2)
C16	0.013 (2)	0.034 (3)	0.027 (3)	0.000 (2)	0.001 (2)	0.002 (2)
C17	0.026 (3)	0.026 (3)	0.023 (3)	0.007 (2)	0.006 (2)	0.002 (2)
C18	0.021 (3)	0.027 (3)	0.026 (3)	0.004 (2)	0.002 (2)	0.002 (2)
C19	0.022 (3)	0.029 (3)	0.022 (3)	0.004 (2)	0.002 (2)	0.000 (2)
C20	0.019 (3)	0.045 (3)	0.038 (3)	0.009 (2)	0.002 (2)	−0.013 (3)
C21	0.089 (3)	0.075 (3)	0.048 (2)	0.023 (3)	0.009 (2)	−0.020 (2)
C22	0.089 (3)	0.075 (3)	0.048 (2)	0.023 (3)	0.009 (2)	−0.020 (2)
C23	0.089 (3)	0.075 (3)	0.048 (2)	0.023 (3)	0.009 (2)	−0.020 (2)
C24	0.029 (3)	0.024 (3)	0.026 (3)	0.002 (2)	0.007 (2)	0.003 (2)
C25	0.030 (3)	0.024 (3)	0.027 (3)	0.005 (2)	0.009 (2)	0.004 (2)
C26	0.032 (3)	0.026 (3)	0.031 (3)	0.003 (2)	0.016 (2)	0.001 (2)
C27	0.027 (3)	0.022 (3)	0.055 (4)	−0.002 (2)	0.019 (3)	−0.002 (2)
C28	0.022 (3)	0.035 (3)	0.040 (3)	0.004 (2)	0.002 (2)	0.001 (2)
C29	0.019 (3)	0.031 (3)	0.033 (3)	0.007 (2)	0.005 (2)	0.006 (2)
C30	0.022 (3)	0.031 (3)	0.027 (3)	0.006 (2)	0.010 (2)	0.005 (2)
C31	0.020 (2)	0.045 (3)	0.031 (2)	0.009 (2)	0.0063 (19)	−0.001 (2)
C31A	0.020 (2)	0.045 (3)	0.031 (2)	0.009 (2)	0.0063 (19)	−0.001 (2)
C32	0.031 (3)	0.048 (3)	0.031 (3)	0.013 (3)	0.001 (2)	0.007 (2)
C33	0.043 (4)	0.074 (5)	0.032 (3)	0.007 (3)	0.004 (3)	0.013 (3)
C34	0.063 (5)	0.060 (4)	0.044 (4)	0.015 (4)	−0.002 (3)	−0.007 (3)
C35	0.043 (4)	0.094 (5)	0.045 (4)	0.029 (4)	0.000 (3)	0.022 (4)
O2W	0.111 (6)	0.140 (6)	0.190 (7)	0.071 (5)	0.044 (5)	0.104 (6)
O3W	0.113 (5)	0.104 (5)	0.094 (4)	0.004 (4)	0.025 (4)	0.038 (4)
O1W	0.095 (4)	0.068 (3)	0.065 (3)	0.004 (3)	0.023 (3)	0.021 (3)

Geometric parameters (Å, º)

Zn1—O1	1.972 (4)	C14—H14	0.9500
Zn1—O5	1.986 (3)	C14—C15	1.392 (6)
Zn1—O7A^i	2.074 (7)	C15—C16	1.390 (6)
Zn1—O8^i	1.951 (8)	C15—C20	1.533 (7)
Zn1—O8A^i	2.361 (8)	C16—H16	0.9500
Zn1—N1	2.034 (4)	C16—C17	1.394 (6)
Zn2—O2	2.025 (3)	C17—C18	1.398 (7)
Zn2—O3^ii	2.009 (3)	C17—C19	1.491 (7)
Zn2—O6	2.017 (3)	C18—H18	0.9500
Zn2—O10	2.092 (4)	C20—C21	1.494 (9)
Zn2—N4^iii	2.140 (4)	C20—C22	1.561 (9)
O1—C12	1.259 (6)	C20—C23	1.503 (9)
O2—C12	1.247 (6)	C21—H21A	0.9800
O3—C19	1.259 (5)	C21—H21B	0.9800
O4—C19	1.254 (6)	C21—H21C	0.9800
O5—C24	1.270 (6)	C22—H22A	0.9800
O6—C24	1.265 (5)	C22—H22B	0.9800
O7—C31	1.259 (14)	C22—H22C	0.9800
O7A—C31A	1.287 (14)	C23—H23A	0.9800
O8—C31	1.246 (14)	C23—H23B	0.9800
O8A—C31A	1.246 (15)	C23—H23C	0.9800
O9—C6	1.218 (6)	C24—C25	1.490 (7)
O10—H10A	0.8944	C25—C26	1.394 (7)
O10—H10B	0.8969	C25—C30	1.393 (6)
N1—C1	1.334 (6)	C26—H26	0.9500
N1—C5	1.347 (6)	C26—C27	1.383 (7)
N2—H2	0.8800	C27—C28	1.389 (7)
N2—C3	1.379 (7)	C27—C31	1.512 (15)
N2—C6	1.384 (6)	C27—C31A	1.534 (16)
N3—H3	0.8800	C28—H28	0.9500
N3—C6	1.374 (7)	C28—C29	1.391 (7)
N3—C9	1.388 (6)	C29—C30	1.392 (6)
N4—C7	1.330 (7)	C29—C32	1.537 (7)
N4—C11	1.347 (6)	C30—H30	0.9500
C1—H1	0.9500	C32—C33	1.533 (8)
C1—C2	1.382 (7)	C32—C34	1.534 (8)
C2—H2A	0.9500	C32—C35	1.516 (7)
C2—C3	1.384 (7)	C33—H33A	0.9800
C3—C4	1.402 (7)	C33—H33B	0.9800
C4—H4	0.9500	C33—H33C	0.9800
C4—C5	1.369 (7)	C34—H34A	0.9800
C5—H5	0.9500	C34—H34B	0.9800
C7—H7	0.9500	C34—H34C	0.9800
C7—C8	1.398 (7)	C35—H35A	0.9800
C8—H8	0.9500	C35—H35B	0.9800
C8—C9	1.381 (7)	C35—H35C	0.9800
C9—C10	1.384 (7)	O2W—H2WA	0.8697
C10—H10	0.9500	O2W—H2WB	0.8701
C10—C11	1.365 (7)	O3W—H3WA	0.8700
C11—H11	0.9500	O3W—H3WB	0.8699
C12—C13	1.507 (6)	O1W—H1WA	0.8698
C13—C14	1.395 (6)	O1W—H1WB	0.8702
C13—C18	1.392 (6)
O1—Zn1—O5	109.03 (15)	C16—C15—C20	120.5 (4)
O1—Zn1—O7A^i	104.2 (2)	C15—C16—H16	118.8
O1—Zn1—O8A^i	84.1 (2)	C15—C16—C17	122.5 (4)
O1—Zn1—N1	112.35 (16)	C17—C16—H16	118.8
O1—Zn1—C31A^i	94.5 (3)	C16—C17—C18	119.2 (4)
O5—Zn1—O7A^i	93.7 (2)	C16—C17—C19	120.8 (4)
O5—Zn1—O8A^i	152.6 (2)	C18—C17—C19	119.9 (4)
O5—Zn1—N1	105.32 (15)	C13—C18—C17	119.3 (4)
O5—Zn1—C31A^i	123.8 (3)	C13—C18—H18	120.3
O7A^i—Zn1—C31A^i	30.1 (3)	C17—C18—H18	120.3
O8^i—Zn1—O1	100.0 (3)	O3—C19—C17	117.3 (4)
O8^i—Zn1—O5	133.3 (3)	O4—C19—O3	122.5 (4)
O8^i—Zn1—O7A^i	43.0 (3)	O4—C19—C17	120.2 (4)
O8^i—Zn1—O8A^i	20.1 (3)	C15—C20—C22	107.9 (5)
O8^i—Zn1—N1	95.9 (3)	C21—C20—C15	113.2 (4)
O8^i—Zn1—C31A^i	15.7 (4)	C21—C20—C22	104.2 (5)
O8A^i—Zn1—C31A^i	29.1 (3)	C21—C20—C23	114.3 (6)
N1—Zn1—O7A^i	129.6 (2)	C23—C20—C15	111.6 (4)
N1—Zn1—O8A^i	90.7 (2)	C23—C20—C22	104.9 (5)
N1—Zn1—C31A^i	111.5 (3)	C20—C21—H21A	109.5
O2—Zn2—O10	87.00 (16)	C20—C21—H21B	109.5
O2—Zn2—N4^iii	85.75 (15)	C20—C21—H21C	109.5
O3^ii—Zn2—O2	142.77 (14)	H21A—C21—H21B	109.5
O3^ii—Zn2—O6	103.49 (14)	H21A—C21—H21C	109.5
O3^ii—Zn2—O10	88.12 (15)	H21B—C21—H21C	109.5
O3^ii—Zn2—N4^iii	93.10 (15)	C20—C22—H22A	109.5
O6—Zn2—O2	113.62 (14)	C20—C22—H22B	109.5
O6—Zn2—O10	93.17 (16)	C20—C22—H22C	109.5
O6—Zn2—N4^iii	96.64 (15)	H22A—C22—H22B	109.5
O10—Zn2—N4^iii	169.53 (17)	H22A—C22—H22C	109.5
C12—O1—Zn1	140.4 (4)	H22B—C22—H22C	109.5
C12—O2—Zn2	130.1 (3)	C20—C23—H23A	109.5
C19—O3—Zn2^i	108.0 (3)	C20—C23—H23B	109.5
C24—O5—Zn1	116.9 (3)	C20—C23—H23C	109.5
C24—O6—Zn2	130.1 (3)	H23A—C23—H23B	109.5
C31—O8—Zn1^ii	107.2 (8)	H23A—C23—H23C	109.5
Zn2—O10—H10A	109.6	H23B—C23—H23C	109.5
Zn2—O10—H10B	111.9	O5—C24—C25	118.3 (4)
H10A—O10—H10B	102.2	O6—C24—O5	122.3 (5)
C1—N1—Zn1	121.4 (4)	O6—C24—C25	119.5 (4)
C1—N1—C5	117.2 (4)	C26—C25—C24	120.9 (4)
C5—N1—Zn1	121.2 (3)	C30—C25—C24	119.7 (4)
C3—N2—H2	116.4	C30—C25—C26	119.4 (5)
C3—N2—C6	127.1 (4)	C25—C26—H26	120.2
C6—N2—H2	116.4	C27—C26—C25	119.5 (5)
C6—N3—H3	116.1	C27—C26—H26	120.2
C6—N3—C9	127.9 (4)	C26—C27—C28	119.9 (5)
C9—N3—H3	116.1	C26—C27—C31	129.5 (6)
C7—N4—Zn2^iii	125.5 (3)	C26—C27—C31A	110.7 (6)
C7—N4—C11	116.5 (4)	C28—C27—C31	110.3 (6)
C11—N4—Zn2^iii	117.7 (4)	C28—C27—C31A	129.3 (6)
N1—C1—H1	118.3	C27—C28—H28	118.9
N1—C1—C2	123.4 (5)	C27—C28—C29	122.2 (5)
C2—C1—H1	118.3	C29—C28—H28	118.9
C1—C2—H2A	120.3	C28—C29—C30	116.8 (5)
C1—C2—C3	119.5 (5)	C28—C29—C32	121.3 (4)
C3—C2—H2A	120.3	C30—C29—C32	121.9 (4)
N2—C3—C2	125.1 (5)	C25—C30—H30	118.9
N2—C3—C4	117.8 (5)	C29—C30—C25	122.2 (4)
C2—C3—C4	117.1 (5)	C29—C30—H30	118.9
C3—C4—H4	120.1	O7—C31—C27	123.7 (10)
C5—C4—C3	119.8 (5)	O8—C31—O7	122.4 (12)
C5—C4—H4	120.1	O8—C31—C27	113.8 (10)
N1—C5—C4	123.0 (5)	O7A—C31A—C27	112.9 (10)
N1—C5—H5	118.5	O8A—C31A—O7A	121.1 (13)
C4—C5—H5	118.5	O8A—C31A—C27	126.0 (10)
O9—C6—N2	123.6 (5)	C27—C31A—Zn1^ii	166.9 (7)
O9—C6—N3	125.0 (5)	C33—C32—C29	110.2 (4)
N3—C6—N2	111.3 (4)	C33—C32—C34	108.2 (5)
N4—C7—H7	118.1	C34—C32—C29	108.1 (4)
N4—C7—C8	123.8 (5)	C35—C32—C29	112.3 (4)
C8—C7—H7	118.1	C35—C32—C33	108.5 (5)
C7—C8—H8	120.8	C35—C32—C34	109.5 (5)
C9—C8—C7	118.4 (5)	C32—C33—H33A	109.5
C9—C8—H8	120.8	C32—C33—H33B	109.5
C8—C9—N3	126.1 (5)	C32—C33—H33C	109.5
C8—C9—C10	118.0 (5)	H33A—C33—H33B	109.5
C10—C9—N3	115.9 (4)	H33A—C33—H33C	109.5
C9—C10—H10	120.2	H33B—C33—H33C	109.5
C11—C10—C9	119.7 (5)	C32—C34—H34A	109.5
C11—C10—H10	120.2	C32—C34—H34B	109.5
N4—C11—C10	123.6 (5)	C32—C34—H34C	109.5
N4—C11—H11	118.2	H34A—C34—H34B	109.5
C10—C11—H11	118.2	H34A—C34—H34C	109.5
O1—C12—C13	117.3 (4)	H34B—C34—H34C	109.5
O2—C12—O1	125.3 (4)	C32—C35—H35A	109.5
O2—C12—C13	117.4 (4)	C32—C35—H35B	109.5
C14—C13—C12	119.5 (4)	C32—C35—H35C	109.5
C18—C13—C12	120.5 (4)	H35A—C35—H35B	109.5
C18—C13—C14	119.9 (4)	H35A—C35—H35C	109.5
C13—C14—H14	119.1	H35B—C35—H35C	109.5
C15—C14—C13	121.8 (4)	H2WA—O2W—H2WB	104.5
C15—C14—H14	119.1	H3WA—O3W—H3WB	104.5
C14—C15—C20	122.4 (4)	H1WA—O1W—H1WB	104.5
C16—C15—C14	117.1 (4)
Zn1—O1—C12—O2	67.4 (8)	C12—C13—C14—C15	−178.5 (4)
Zn1—O1—C12—C13	−114.1 (5)	C12—C13—C18—C17	−178.9 (4)
Zn1—O5—C24—O6	0.1 (6)	C13—C14—C15—C16	−2.5 (7)
Zn1—O5—C24—C25	179.2 (3)	C13—C14—C15—C20	177.8 (5)
Zn1^ii—O7A—C31A—O8A	0.1 (14)	C14—C13—C18—C17	3.5 (7)
Zn1^ii—O7A—C31A—C27	179.5 (8)	C14—C15—C16—C17	3.5 (7)
Zn1^ii—O8—C31—O7	−1.9 (15)	C14—C15—C20—C21	0.7 (8)
Zn1^ii—O8—C31—C27	−178.7 (7)	C14—C15—C20—C22	115.4 (6)
Zn1^ii—O8A—C31A—O7A	−0.1 (12)	C14—C15—C20—C23	−129.9 (6)
Zn1^ii—O8A—C31A—C27	−179.4 (13)	C15—C16—C17—C18	−1.0 (7)
Zn1—N1—C1—C2	−175.5 (4)	C15—C16—C17—C19	−179.9 (4)
Zn1—N1—C5—C4	175.8 (4)	C16—C15—C20—C21	−179.0 (5)
Zn2—O2—C12—O1	−26.6 (8)	C16—C15—C20—C22	−64.3 (6)
Zn2—O2—C12—C13	155.0 (3)	C16—C15—C20—C23	50.4 (7)
Zn2^i—O3—C19—O4	−1.4 (6)	C16—C17—C18—C13	−2.6 (7)
Zn2^i—O3—C19—C17	178.2 (3)	C16—C17—C19—O3	−161.0 (4)
Zn2—O6—C24—O5	−94.7 (5)	C16—C17—C19—O4	18.6 (7)
Zn2—O6—C24—C25	86.2 (5)	C18—C13—C14—C15	−0.9 (7)
Zn2^iii—N4—C7—C8	−172.4 (4)	C18—C17—C19—O3	20.1 (7)
Zn2^iii—N4—C11—C10	173.3 (4)	C18—C17—C19—O4	−160.3 (4)
O1—C12—C13—C14	−178.1 (5)	C19—C17—C18—C13	176.4 (4)
O1—C12—C13—C18	4.4 (7)	C20—C15—C16—C17	−176.8 (5)
O2—C12—C13—C14	0.5 (7)	C24—C25—C26—C27	−178.0 (4)
O2—C12—C13—C18	−177.1 (4)	C24—C25—C30—C29	176.5 (4)
O5—C24—C25—C26	180.0 (4)	C25—C26—C27—C28	1.0 (7)
O5—C24—C25—C30	0.8 (7)	C25—C26—C27—C31	174.0 (8)
O6—C24—C25—C26	−0.9 (7)	C25—C26—C27—C31A	−175.9 (7)
O6—C24—C25—C30	179.9 (4)	C26—C25—C30—C29	−2.7 (7)
N1—C1—C2—C3	0.2 (8)	C26—C27—C28—C29	−1.8 (8)
N2—C3—C4—C5	−178.6 (5)	C26—C27—C31—O7	−136.4 (10)
N3—C9—C10—C11	−177.1 (5)	C26—C27—C31—O8	40.4 (14)
N4—C7—C8—C9	0.7 (8)	C26—C27—C31A—Zn1^ii	−174 (4)
C1—N1—C5—C4	−0.4 (7)	C26—C27—C31A—O7A	−175.9 (9)
C1—C2—C3—N2	178.9 (5)	C26—C27—C31A—O8A	3.5 (16)
C1—C2—C3—C4	−1.4 (7)	C27—C28—C29—C30	0.3 (7)
C2—C3—C4—C5	1.6 (7)	C27—C28—C29—C32	−179.2 (5)
C3—N2—C6—O9	−0.7 (9)	C28—C27—C31—O7	37.2 (14)
C3—N2—C6—N3	−179.9 (5)	C28—C27—C31—O8	−146.0 (9)
C3—C4—C5—N1	−0.7 (8)	C28—C27—C31A—Zn1^ii	9 (4)
C5—N1—C1—C2	0.7 (7)	C28—C27—C31A—O7A	7.5 (15)
C6—N2—C3—C2	−2.7 (8)	C28—C27—C31A—O8A	−173.1 (10)
C6—N2—C3—C4	177.5 (5)	C28—C29—C30—C25	2.0 (7)
C6—N3—C9—C8	−4.8 (8)	C28—C29—C32—C33	−142.4 (5)
C6—N3—C9—C10	174.5 (5)	C28—C29—C32—C34	99.6 (6)
C7—N4—C11—C10	0.0 (8)	C28—C29—C32—C35	−21.4 (7)
C7—C8—C9—N3	177.3 (5)	C30—C25—C26—C27	1.2 (7)
C7—C8—C9—C10	−2.0 (7)	C30—C29—C32—C33	38.0 (7)
C8—C9—C10—C11	2.3 (7)	C30—C29—C32—C34	−80.0 (6)
C9—N3—C6—O9	6.6 (9)	C30—C29—C32—C35	159.1 (5)
C9—N3—C6—N2	−174.2 (5)	C31—C27—C28—C29	−176.1 (7)
C9—C10—C11—N4	−1.3 (8)	C31A—C27—C28—C29	174.5 (8)
C11—N4—C7—C8	0.3 (8)	C32—C29—C30—C25	−178.5 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O2W	0.89	1.88	2.658 (7)	144
O10—H10B···O1W	0.90	1.98	2.768 (7)	146
N3—H3···O4^iv	0.88	1.92	2.761 (5)	160
C2—H2A···O9	0.95	2.23	2.840 (6)	121
C8—H8···O9	0.95	2.34	2.921 (7)	119
C11—H11···O2^iii	0.95	2.44	2.936 (6)	113
C26—H26···O8A	0.95	2.39	2.770 (9)	103
O1W—H1WA···O1W^v	0.87	2.34	2.918 (10)	124
O2W—H2WA···O7^vi	0.87	1.92	2.708 (11)	149
O2W—H2WB···O3W^vi	0.87	2.38	2.934 (10)	122
O3W—H3WA···O1^v	0.87	2.10	2.941 (7)	164
O3W—H3WB···O2W	0.87	2.11	2.912 (11)	154

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