Crystal structure of poly[bis­(μ-nicotinamide-κ²N¹:O)bis­(μ-4-nitro­benzoato-κ²O¹:O^1′)zinc]

The asymmetric unit of the title zinc(II) coordination polymer contains two 4-nitro­benzoate (NB) anions and two nicotinamide (NA) ligands. Only one of the two NB anions and one of the two NA ligands bridge adjacent Zn^II ions through eight- and 12-membered rings, respectively, forming polymeric chains running along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.073
• wR factor = 0.238
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16 Report
PLAT213_ALERT_2_C Atom O3              has ADP max/min Ratio .....        3.3 prolat
PLAT220_ALERT_2_C Large Non-Solvent  O     Ueq(max)/Ueq(min) Range        4.0 Ratio
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         N1 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.1 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .         13 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      13.68

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.15 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  O2      ..        9.9 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  O6      ..        8.6 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  N3      ..        9.0 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  N5      ..        7.7 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  O10_a   ..        9.6 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Zn1    --  O5_b    ..       11.8 su
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Poly[bis(µ-nicotinamide-κ²N¹:O)bis(µ-4-nitrobenzoato-κ²O¹:O^1')zinc]

Crystal data

[Zn(C6H6N2O)2(C7H4NO4)2]	Z = 2
Mr = 641.87	F(000) = 656
Triclinic, P1	Dx = 1.628 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5118 (3) Å	Cell parameters from 9922 reflections
b = 10.5591 (3) Å	θ = 2.5–28.4°
c = 14.5326 (5) Å	µ = 1.01 mm^−1
α = 109.846 (4)°	T = 296 K
β = 93.618 (3)°	Block, yellow
γ = 104.815 (4)°	0.50 × 0.37 × 0.33 mm
V = 1309.11 (9) Å^3

Data collection

Bruker SMART BREEZE CCD diffractometer	6520 independent reflections
Radiation source: fine-focus sealed tube	5816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −12→12
Tmin = 0.635, Tmax = 0.705	k = −13→14
34333 measured reflections	l = −19→19

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.238	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.149P)^2 + 3.1586P] where P = (Fo^2 + 2Fc^2)/3
6520 reflections	(Δ/σ)max < 0.001
388 parameters	Δρmax = 1.29 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

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. 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 > 2sigma(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	0.88909 (4)	0.14132 (4)	0.11465 (3)	0.02880 (19)
O1	0.8671 (3)	0.4391 (3)	0.3500 (2)	0.0410 (8)
O2	0.9117 (3)	0.3588 (3)	0.19518 (19)	0.0266 (5)
O3	1.5920 (5)	0.8555 (6)	0.3452 (4)	0.0923 (19)
O4	1.5777 (4)	0.8861 (4)	0.4965 (3)	0.0560 (10)
O5	1.1523 (3)	0.0826 (2)	−0.05180 (18)	0.0230 (5)
O6	1.1170 (3)	0.2086 (3)	0.09758 (19)	0.0266 (5)
O7	1.8536 (4)	0.5337 (5)	0.0411 (4)	0.0741 (14)
O8	1.8302 (4)	0.6372 (4)	0.1922 (4)	0.0651 (12)
O9	1.4003 (3)	0.3463 (3)	0.3975 (2)	0.0315 (6)
O10	0.3467 (2)	−0.0828 (3)	−0.14454 (17)	0.0235 (5)
N1	1.5271 (4)	0.8314 (4)	0.4092 (3)	0.0437 (9)
N2	1.7850 (4)	0.5475 (4)	0.1102 (4)	0.0464 (10)
N3	0.9685 (3)	0.1292 (3)	0.2625 (2)	0.0209 (5)
N4	1.3297 (3)	0.4235 (4)	0.5466 (2)	0.0301 (7)
H4A	1.4152	0.4830	0.5733	0.036*
H4B	1.2605	0.4171	0.5816	0.036*
N5	0.7923 (3)	0.1216 (3)	−0.0391 (2)	0.0192 (5)
N6	0.3979 (3)	−0.2171 (3)	−0.2888 (2)	0.0257 (6)
H6A	0.3090	−0.2722	−0.3076	0.031*
H6B	0.4633	−0.2315	−0.3263	0.031*
C1	0.9464 (4)	0.4401 (3)	0.2850 (3)	0.0231 (6)
C2	1.0981 (4)	0.5454 (3)	0.3168 (2)	0.0212 (6)
C3	1.1568 (4)	0.6153 (4)	0.4178 (3)	0.0337 (8)
H3	1.1008	0.5981	0.4648	0.040*
C4	1.2969 (5)	0.7097 (5)	0.4486 (3)	0.0377 (9)
H4	1.3356	0.7566	0.5157	0.045*
C5	1.3777 (4)	0.7324 (4)	0.3772 (3)	0.0295 (8)
C6	1.3225 (4)	0.6662 (5)	0.2774 (3)	0.0351 (8)
H6	1.3786	0.6851	0.2309	0.042*
C7	1.1821 (4)	0.5709 (4)	0.2470 (3)	0.0298 (8)
H7	1.1444	0.5241	0.1798	0.036*
C8	1.1944 (3)	0.1804 (3)	0.0309 (2)	0.0161 (5)
C9	1.3506 (3)	0.2755 (3)	0.0529 (2)	0.0170 (6)
C10	1.4151 (4)	0.3680 (4)	0.1489 (3)	0.0291 (7)
H10	1.3613	0.3707	0.2004	0.035*
C11	1.5580 (4)	0.4561 (5)	0.1691 (3)	0.0359 (9)
H11	1.6008	0.5176	0.2333	0.043*
C12	1.6357 (4)	0.4502 (4)	0.0910 (3)	0.0300 (8)
C13	1.5764 (4)	0.3579 (4)	−0.0052 (3)	0.0334 (8)
H13	1.6314	0.3547	−0.0562	0.040*
C14	1.4334 (4)	0.2706 (4)	−0.0237 (3)	0.0269 (7)
H14	1.3919	0.2079	−0.0879	0.032*
C15	1.1025 (3)	0.2154 (3)	0.3102 (2)	0.0198 (6)
H15	1.1637	0.2597	0.2758	0.024*
C16	1.1542 (3)	0.2416 (3)	0.4080 (2)	0.0188 (6)
C17	1.0644 (4)	0.1754 (4)	0.4601 (3)	0.0308 (8)
H17	1.0946	0.1935	0.5266	0.037*
C18	0.9282 (4)	0.0815 (5)	0.4100 (3)	0.0363 (9)
H18	0.8671	0.0319	0.4417	0.044*
C19	0.8841 (4)	0.0623 (4)	0.3123 (3)	0.0275 (7)
H19	0.7920	0.0002	0.2799	0.033*
C20	1.3046 (3)	0.3414 (3)	0.4512 (2)	0.0203 (6)
C21	0.6540 (3)	0.0355 (3)	−0.0750 (2)	0.0176 (6)
H21	0.5976	0.0097	−0.0307	0.021*
C22	0.5908 (3)	−0.0170 (3)	−0.1739 (2)	0.0154 (5)
C23	0.6756 (4)	0.0196 (4)	−0.2406 (3)	0.0247 (7)
H23	0.6386	−0.0170	−0.3081	0.030*
C24	0.8167 (4)	0.1120 (4)	−0.2041 (3)	0.0299 (8)
H24	0.8746	0.1411	−0.2466	0.036*
C25	0.8706 (3)	0.1609 (4)	−0.1032 (3)	0.0241 (7)
H25	0.9651	0.2234	−0.0794	0.029*
C26	0.4345 (3)	−0.1097 (3)	−0.2019 (2)	0.0156 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0193 (3)	0.0303 (3)	0.0256 (3)	0.00170 (18)	0.00168 (17)	0.00104 (19)
O1	0.0224 (13)	0.0400 (16)	0.0361 (16)	−0.0070 (11)	0.0135 (11)	−0.0058 (12)
O2	0.0249 (12)	0.0188 (11)	0.0245 (12)	0.0026 (9)	−0.0005 (9)	−0.0028 (9)
O3	0.045 (2)	0.110 (4)	0.081 (3)	−0.040 (3)	0.011 (2)	0.031 (3)
O4	0.0332 (17)	0.050 (2)	0.062 (2)	−0.0093 (15)	−0.0172 (16)	0.0128 (18)
O5	0.0187 (11)	0.0177 (11)	0.0223 (11)	0.0009 (9)	−0.0003 (9)	−0.0014 (9)
O6	0.0118 (11)	0.0315 (13)	0.0234 (12)	−0.0019 (9)	0.0054 (9)	−0.0002 (10)
O7	0.0295 (18)	0.081 (3)	0.101 (4)	−0.0137 (18)	0.022 (2)	0.040 (3)
O8	0.0286 (17)	0.046 (2)	0.096 (3)	−0.0137 (15)	−0.0084 (19)	0.018 (2)
O9	0.0135 (11)	0.0370 (14)	0.0249 (12)	−0.0004 (10)	0.0065 (9)	−0.0068 (10)
O10	0.0099 (10)	0.0289 (12)	0.0188 (11)	0.0011 (9)	0.0031 (8)	−0.0038 (9)
N1	0.0233 (16)	0.0369 (19)	0.059 (2)	−0.0085 (14)	−0.0031 (16)	0.0177 (18)
N2	0.0146 (15)	0.040 (2)	0.085 (3)	−0.0043 (14)	0.0024 (17)	0.033 (2)
N3	0.0121 (12)	0.0215 (13)	0.0204 (13)	−0.0026 (10)	−0.0018 (9)	0.0036 (10)
N4	0.0171 (13)	0.0356 (17)	0.0186 (14)	−0.0027 (12)	0.0024 (10)	−0.0055 (12)
N5	0.0084 (11)	0.0199 (12)	0.0218 (13)	−0.0016 (9)	−0.0011 (9)	0.0034 (10)
N6	0.0143 (12)	0.0277 (15)	0.0193 (13)	−0.0015 (10)	0.0047 (10)	−0.0054 (11)
C1	0.0163 (14)	0.0167 (14)	0.0266 (16)	0.0015 (11)	0.0037 (12)	−0.0015 (12)
C2	0.0168 (14)	0.0168 (14)	0.0223 (15)	0.0006 (11)	0.0027 (11)	0.0012 (11)
C3	0.0270 (18)	0.038 (2)	0.0215 (16)	−0.0058 (15)	0.0042 (13)	0.0036 (15)
C4	0.030 (2)	0.041 (2)	0.0248 (18)	−0.0070 (17)	−0.0043 (15)	0.0061 (16)
C5	0.0173 (15)	0.0241 (17)	0.039 (2)	−0.0046 (13)	−0.0007 (14)	0.0107 (15)
C6	0.0282 (19)	0.037 (2)	0.034 (2)	−0.0034 (15)	0.0099 (15)	0.0140 (16)
C7	0.0275 (18)	0.0305 (18)	0.0213 (16)	−0.0030 (14)	0.0043 (13)	0.0055 (14)
C8	0.0091 (12)	0.0141 (13)	0.0211 (14)	0.0007 (10)	0.0018 (10)	0.0037 (11)
C9	0.0098 (12)	0.0141 (13)	0.0237 (15)	0.0011 (10)	0.0036 (11)	0.0044 (11)
C10	0.0178 (15)	0.0339 (19)	0.0231 (16)	−0.0056 (13)	0.0014 (12)	0.0052 (14)
C11	0.0220 (17)	0.037 (2)	0.0325 (19)	−0.0087 (15)	−0.0044 (14)	0.0066 (16)
C12	0.0115 (14)	0.0246 (17)	0.053 (2)	−0.0024 (12)	0.0013 (14)	0.0205 (16)
C13	0.0211 (17)	0.036 (2)	0.047 (2)	0.0062 (15)	0.0187 (16)	0.0191 (18)
C14	0.0214 (16)	0.0251 (16)	0.0289 (17)	0.0023 (13)	0.0110 (13)	0.0056 (13)
C15	0.0125 (13)	0.0224 (15)	0.0176 (14)	−0.0010 (11)	0.0008 (10)	0.0035 (11)
C16	0.0115 (13)	0.0202 (14)	0.0176 (14)	0.0003 (11)	−0.0003 (10)	0.0020 (11)
C17	0.0218 (16)	0.041 (2)	0.0258 (17)	−0.0033 (15)	−0.0018 (13)	0.0171 (16)
C18	0.0227 (17)	0.045 (2)	0.037 (2)	−0.0087 (16)	−0.0014 (15)	0.0245 (18)
C19	0.0145 (14)	0.0291 (17)	0.0321 (18)	−0.0062 (12)	−0.0023 (12)	0.0133 (14)
C20	0.0119 (13)	0.0220 (15)	0.0178 (14)	0.0015 (11)	−0.0009 (10)	−0.0009 (12)
C21	0.0087 (12)	0.0214 (14)	0.0163 (13)	−0.0003 (10)	0.0006 (10)	0.0028 (11)
C22	0.0083 (12)	0.0182 (13)	0.0172 (13)	0.0027 (10)	0.0024 (10)	0.0041 (11)
C23	0.0169 (15)	0.0356 (18)	0.0205 (15)	0.0023 (13)	0.0042 (12)	0.0129 (14)
C24	0.0168 (15)	0.041 (2)	0.0340 (19)	−0.0005 (14)	0.0056 (13)	0.0225 (16)
C25	0.0106 (13)	0.0252 (16)	0.0347 (18)	−0.0020 (11)	0.0005 (12)	0.0150 (14)
C26	0.0085 (12)	0.0188 (13)	0.0142 (12)	0.0013 (10)	0.0008 (9)	0.0019 (11)

Geometric parameters (Å, º)

Zn1—O2	2.140 (2)	C5—C6	1.377 (6)
Zn1—O5^i	2.142 (2)	C6—H6	0.9300
Zn1—O6	2.160 (2)	C7—C6	1.389 (5)
Zn1—O10^ii	2.280 (2)	C7—H7	0.9300
Zn1—N3	2.288 (3)	C8—C9	1.509 (4)
Zn1—N5	2.282 (3)	C9—C10	1.392 (5)
O1—C1	1.247 (4)	C9—C14	1.399 (4)
O2—C1	1.261 (4)	C10—C11	1.385 (5)
O4—N1	1.208 (6)	C10—H10	0.9300
O5—Zn1^i	2.142 (2)	C11—H11	0.9300
O5—C8	1.248 (4)	C12—C11	1.384 (6)
O6—C8	1.255 (4)	C13—C12	1.384 (6)
O9—C20	1.239 (4)	C13—C14	1.384 (5)
O10—Zn1^ii	2.280 (2)	C13—H13	0.9300
N1—O3	1.210 (6)	C14—H14	0.9300
N2—O7	1.220 (7)	C15—C16	1.383 (4)
N2—O8	1.210 (7)	C15—H15	0.9300
N2—C12	1.469 (4)	C16—C17	1.388 (5)
N3—C15	1.342 (4)	C16—C20	1.489 (4)
N3—C19	1.341 (4)	C17—H17	0.9300
N4—H4A	0.8600	C18—C17	1.388 (5)
N4—H4B	0.8600	C18—H18	0.9300
N5—C21	1.345 (4)	C19—C18	1.384 (5)
N5—C25	1.337 (4)	C19—H19	0.9300
N6—C26	1.332 (4)	C20—N4	1.329 (4)
N6—H6A	0.8600	C21—H21	0.9300
N6—H6B	0.8600	C22—C21	1.384 (4)
C1—C2	1.510 (4)	C22—C23	1.391 (4)
C2—C3	1.401 (5)	C23—C24	1.387 (5)
C2—C7	1.384 (5)	C23—H23	0.9300
C3—C4	1.383 (5)	C24—H24	0.9300
C3—H3	0.9300	C25—C24	1.391 (5)
C4—H4	0.9300	C25—H25	0.9300
C5—N1	1.468 (5)	C26—O10	1.233 (4)
C5—C4	1.379 (6)	C26—C22	1.497 (4)
O2—Zn1—O5^i	170.95 (10)	O5—C8—O6	125.6 (3)
O2—Zn1—O6	86.90 (10)	O5—C8—C9	117.8 (3)
O2—Zn1—O10^ii	89.70 (10)	O6—C8—C9	116.6 (3)
O2—Zn1—N3	87.21 (10)	C10—C9—C8	121.1 (3)
O2—Zn1—N5	99.61 (10)	C10—C9—C14	119.0 (3)
O5^i—Zn1—O6	99.77 (10)	C14—C9—C8	119.9 (3)
O5^i—Zn1—O10^ii	83.34 (9)	C9—C10—H10	119.4
O5^i—Zn1—N3	86.87 (10)	C11—C10—C9	121.1 (3)
O5^i—Zn1—N5	85.89 (10)	C11—C10—H10	119.4
O6—Zn1—O10^ii	175.66 (8)	C10—C11—H11	120.9
O6—Zn1—N3	88.43 (10)	C12—C11—C10	118.3 (4)
O6—Zn1—N5	95.75 (10)	C12—C11—H11	120.9
O10^ii—Zn1—N3	88.71 (9)	C11—C12—N2	119.1 (4)
O10^ii—Zn1—N5	87.48 (9)	C13—C12—N2	118.6 (4)
N5—Zn1—N3	172.16 (10)	C13—C12—C11	122.3 (3)
C1—O2—Zn1	135.7 (2)	C12—C13—H13	120.7
C8—O5—Zn1^i	138.9 (2)	C14—C13—C12	118.5 (3)
C8—O6—Zn1	137.8 (2)	C14—C13—H13	120.7
C26—O10—Zn1^ii	147.3 (2)	C9—C14—H14	119.6
O3—N1—C5	117.1 (4)	C13—C14—C9	120.8 (3)
O4—N1—O3	123.5 (4)	C13—C14—H14	119.6
O4—N1—C5	119.3 (4)	N3—C15—C16	123.3 (3)
O7—N2—C12	117.3 (4)	N3—C15—H15	118.3
O8—N2—O7	124.5 (4)	C16—C15—H15	118.3
O8—N2—C12	118.2 (4)	C15—C16—C17	119.0 (3)
C15—N3—Zn1	116.4 (2)	C15—C16—C20	117.1 (3)
C19—N3—Zn1	125.3 (2)	C17—C16—C20	123.9 (3)
C19—N3—C15	117.4 (3)	C16—C17—H17	121.0
C20—N4—H4A	120.0	C18—C17—C16	118.0 (3)
C20—N4—H4B	120.0	C18—C17—H17	121.0
H4A—N4—H4B	120.0	C17—C18—H18	120.3
C21—N5—Zn1	115.9 (2)	C19—C18—C17	119.3 (3)
C25—N5—Zn1	124.9 (2)	C19—C18—H18	120.3
C25—N5—C21	117.3 (3)	N3—C19—C18	122.9 (3)
C26—N6—H6A	120.0	N3—C19—H19	118.5
C26—N6—H6B	120.0	C18—C19—H19	118.5
H6A—N6—H6B	120.0	O9—C20—N4	122.6 (3)
O1—C1—O2	125.5 (3)	O9—C20—C16	119.4 (3)
O1—C1—C2	117.3 (3)	N4—C20—C16	118.0 (3)
O2—C1—C2	117.1 (3)	N5—C21—C22	123.9 (3)
C3—C2—C1	119.9 (3)	N5—C21—H21	118.0
C7—C2—C1	120.6 (3)	C22—C21—H21	118.0
C7—C2—C3	119.4 (3)	C21—C22—C23	118.2 (3)
C2—C3—H3	119.5	C21—C22—C26	117.5 (3)
C4—C3—C2	120.9 (3)	C23—C22—C26	124.3 (3)
C4—C3—H3	119.5	C22—C23—H23	120.8
C3—C4—H4	120.9	C24—C23—C22	118.4 (3)
C5—C4—C3	118.2 (4)	C24—C23—H23	120.8
C5—C4—H4	120.9	C23—C24—C25	119.4 (3)
C6—C5—C4	122.2 (3)	C23—C24—H24	120.3
C6—C5—N1	119.2 (4)	C25—C24—H24	120.3
C4—C5—N1	118.7 (4)	N5—C25—C24	122.7 (3)
C5—C6—C7	119.3 (3)	N5—C25—H25	118.7
C5—C6—H6	120.4	C24—C25—H25	118.7
C7—C6—H6	120.4	O10—C26—N6	123.5 (3)
C2—C7—C6	120.0 (3)	O10—C26—C22	119.1 (3)
C2—C7—H7	120.0	N6—C26—C22	117.4 (3)
C6—C7—H7	120.0
O6—Zn1—O2—C1	−91.7 (3)	C1—C2—C7—C6	−178.9 (4)
O10^ii—Zn1—O2—C1	85.6 (3)	C3—C2—C7—C6	−0.7 (6)
N3—Zn1—O2—C1	−3.1 (3)	C2—C3—C4—C5	−0.4 (7)
N5—Zn1—O2—C1	173.0 (3)	C4—C5—N1—O3	−175.7 (5)
O2—Zn1—O6—C8	−138.6 (4)	C4—C5—N1—O4	2.9 (6)
O5^i—Zn1—O6—C8	47.6 (4)	C6—C5—N1—O3	3.8 (7)
N3—Zn1—O6—C8	134.1 (4)	C6—C5—N1—O4	−177.6 (4)
N5—Zn1—O6—C8	−39.2 (4)	N1—C5—C4—C3	−179.4 (4)
O2—Zn1—N3—C15	−59.4 (2)	C6—C5—C4—C3	1.0 (7)
O2—Zn1—N3—C19	108.8 (3)	N1—C5—C6—C7	179.0 (4)
O5^i—Zn1—N3—C15	127.5 (2)	C4—C5—C6—C7	−1.5 (7)
O5^i—Zn1—N3—C19	−64.4 (3)	C2—C7—C6—C5	1.3 (6)
O6—Zn1—N3—C15	27.6 (2)	O5—C8—C9—C10	−167.0 (3)
O6—Zn1—N3—C19	−164.2 (3)	O5—C8—C9—C14	12.4 (4)
O10^ii—Zn1—N3—C15	−149.2 (2)	O6—C8—C9—C10	14.2 (5)
O10^ii—Zn1—N3—C19	19.0 (3)	O6—C8—C9—C14	−166.4 (3)
O2—Zn1—N5—C21	−115.0 (2)	C8—C9—C10—C11	−179.5 (4)
O2—Zn1—N5—C25	81.2 (3)	C14—C9—C10—C11	1.1 (6)
O5^i—Zn1—N5—C21	57.8 (2)	C8—C9—C14—C13	179.4 (3)
O5^i—Zn1—N5—C25	−106.0 (3)	C10—C9—C14—C13	−1.2 (5)
O6—Zn1—N5—C21	157.2 (2)	C9—C10—C11—C12	0.1 (6)
O6—Zn1—N5—C25	−6.6 (3)	N2—C12—C11—C10	177.2 (4)
O10^ii—Zn1—N5—C21	−25.7 (2)	C13—C12—C11—C10	−1.3 (6)
O10^ii—Zn1—N5—C25	170.5 (3)	C14—C13—C12—N2	−177.2 (4)
Zn1—O2—C1—O1	−73.4 (5)	C14—C13—C12—C11	1.2 (6)
Zn1—O2—C1—C2	105.2 (4)	C12—C13—C14—C9	0.1 (6)
Zn1^i—O5—C8—O6	−77.3 (4)	N3—C15—C16—C17	0.4 (5)
Zn1^i—O5—C8—C9	104.0 (3)	N3—C15—C16—C20	−179.1 (3)
Zn1—O6—C8—O5	−7.5 (6)	C15—C16—C17—C18	2.4 (6)
Zn1—O6—C8—C9	171.2 (2)	C20—C16—C17—C18	−178.1 (4)
O7—N2—C12—C11	175.7 (5)	C15—C16—C20—O9	−33.3 (5)
O7—N2—C12—C13	−5.9 (6)	C15—C16—C20—N4	145.8 (3)
O8—N2—C12—C11	−5.8 (6)	C17—C16—C20—O9	147.2 (4)
O8—N2—C12—C13	172.6 (4)	C17—C16—C20—N4	−33.7 (5)
Zn1—N3—C15—C16	166.7 (3)	C19—C18—C17—C16	−3.0 (7)
C19—N3—C15—C16	−2.4 (5)	N3—C19—C18—C17	1.0 (7)
C15—N3—C19—C18	1.7 (6)	C23—C22—C21—N5	0.9 (5)
Zn1—N3—C19—C18	−166.4 (3)	C26—C22—C21—N5	−178.9 (3)
Zn1—N5—C21—C22	−163.3 (2)	C21—C22—C23—C24	−3.0 (5)
C25—N5—C21—C22	1.8 (5)	C26—C22—C23—C24	176.8 (3)
Zn1—N5—C25—C24	161.1 (3)	C22—C23—C24—C25	2.3 (6)
C21—N5—C25—C24	−2.6 (5)	N5—C25—C24—C23	0.5 (6)
O1—C1—C2—C3	13.6 (5)	N6—C26—O10—Zn1^ii	−1.0 (7)
O1—C1—C2—C7	−168.2 (4)	C22—C26—O10—Zn1^ii	178.5 (3)
O2—C1—C2—C3	−165.0 (4)	O10—C26—C22—C21	36.8 (4)
O2—C1—C2—C7	13.1 (5)	O10—C26—C22—C23	−142.9 (3)
C1—C2—C3—C4	178.5 (4)	N6—C26—C22—C21	−143.6 (3)
C7—C2—C3—C4	0.3 (6)	N6—C26—C22—C23	36.6 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1^iii	0.86	2.20	2.851 (4)	132
N6—H6A···O1^ii	0.86	1.98	2.814 (4)	164
N6—H6B···O9^i	0.86	2.09	2.880 (4)	153
C15—H15···O6	0.93	2.45	3.079 (4)	125
C19—H19···O3^iv	0.93	2.57	3.238 (7)	130
C21—H21···O10^ii	0.93	2.38	3.058 (4)	130

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