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The rational selection of ligands is vitally important in the construction of coordination complexes. Two novel ZnII complexes, namely bis­(acetato-κO)bis­[1-(1H-benzotriazol-1-ylmeth­yl)-2-propyl-1H-imidazole-κN3]zinc(II) monohydrate, [Zn(C13H15N5)2(C2H3O2)2]·H2O, (1), and bis­(azido-κN1)bis­[1-(1H-benzo­triazol-1-ylmeth­yl)-2-propyl-1H-imidazole-κN3]zinc(II), [Zn(C13H15N5)2(N3)2], (2), constructed from the asymmetric multidentate imidazole ligand, have been synthesized under mild con­ditions and characterized by elemental analyses, IR spectroscopy and single-crystal X-ray diffraction analysis. Both complexes exhibit a three-dimensional supra­molecular network directed by different inter­molecular inter­actions between discrete mononuclear units. The complexes were also investigated by fluorescence and thermal analyses. The experimental results show that (1) is a promising fluorescence sensor for detecting Fe3+ ions and (2) is effective as an accelerator of the thermal decomposition of ammonium perchlorate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701717X/yf3128sup1.cif
Contains datablocks 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701717X/yf31281sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701717X/yf31282sup3.hkl
Contains datablock 2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205322961701717X/yf3128sup4.pdf
Additional figures: diffraction patterns, and DSC and TGA curves

CCDC references: 1588302; 1588301

Computing details top

For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: CrysAlis PRO (Agilent, 2013). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) for (1); SHELXL2013 (Sheldrick, 2008) for (2). For both structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(acetato-κO)bis[1-(1H-benzotriazol-1-ylmethyl)-2-propyl-1H-imidazole-κN3]zinc(II) monohydrate (1) top
Crystal data top
[Zn(C13H15N5)2(C2H3O2)2]·H2OZ = 2
Mr = 684.07F(000) = 716
Triclinic, P1Dx = 1.405 Mg m3
a = 8.7481 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.9399 (4) ÅCell parameters from 7610 reflections
c = 16.4168 (7) Åθ = 5.0–70.5°
α = 84.921 (3)°µ = 1.52 mm1
β = 88.623 (3)°T = 293 K
γ = 71.161 (3)°0.27 × 0.20 × 0.14 mm
V = 1616.52 (10) Å3
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
5664 independent reflections
Mirror monochromator5308 reflections with I > 2σ(I)
Detector resolution: 15.9737 pixels mm-1Rint = 0.019
ω scansθmax = 67.1°, θmin = 5.0°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
h = 109
Tmin = 0.608, Tmax = 1.000k = 1314
11919 measured reflectionsl = 1917
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.4511P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
5664 reflectionsΔρmax = 0.29 e Å3
428 parametersΔρmin = 0.29 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn11.02757 (3)0.00682 (2)0.25322 (2)0.03908 (9)
O10.95723 (16)0.14326 (11)0.28933 (8)0.0500 (3)
O21.0568 (2)0.21872 (14)0.17489 (9)0.0740 (4)
O31.25782 (16)0.04755 (14)0.22652 (8)0.0583 (3)
O41.3228 (2)0.0966 (2)0.35545 (11)0.0970 (7)
N10.93810 (16)0.08175 (11)0.14324 (8)0.0384 (3)
N20.81844 (17)0.12726 (12)0.02321 (8)0.0417 (3)
N30.5575 (2)0.21495 (14)0.04498 (10)0.0517 (4)
N40.4274 (2)0.18206 (18)0.02071 (12)0.0676 (5)
N50.2985 (2)0.2753 (2)0.02800 (14)0.0766 (6)
N60.95185 (16)0.08900 (12)0.35073 (8)0.0393 (3)
N70.94527 (17)0.19330 (12)0.45456 (8)0.0428 (3)
N80.8640 (2)0.38876 (13)0.50373 (9)0.0491 (4)
N90.8794 (2)0.47218 (16)0.44502 (11)0.0613 (4)
N100.7687 (2)0.57207 (16)0.45548 (13)0.0686 (5)
C10.5775 (3)0.1504 (3)0.24849 (15)0.0760 (7)
H1A0.6641240.1835140.2430720.114*
H1B0.6083440.0811000.2865840.114*
H1C0.4828890.2081630.2680770.114*
C20.5420 (2)0.11704 (19)0.16708 (12)0.0547 (5)
H2A0.5071460.1880450.1295460.066*
H2B0.4535440.0846290.1729870.066*
C30.6874 (2)0.02579 (16)0.13014 (12)0.0486 (4)
H3A0.7337070.0393660.1712310.058*
H3B0.6503280.0061630.0850350.058*
C40.8147 (2)0.07605 (13)0.10024 (10)0.0381 (3)
C51.0226 (2)0.13863 (15)0.09145 (11)0.0428 (4)
H51.1150220.1548780.1057350.051*
C60.9511 (2)0.16673 (15)0.01766 (11)0.0461 (4)
H60.9839730.2049360.0279300.055*
C70.7167 (2)0.12707 (17)0.04604 (11)0.0537 (5)
H7A0.7703530.1415810.0963390.064*
H7B0.7050490.0489800.0460610.064*
C80.5097 (2)0.33359 (17)0.07007 (11)0.0511 (4)
C90.5916 (3)0.40954 (19)0.10200 (13)0.0614 (5)
H90.7026740.3835350.1102540.074*
C100.4980 (3)0.5257 (2)0.12063 (16)0.0752 (7)
H100.5477470.5797200.1422060.090*
C110.3329 (4)0.5653 (2)0.10856 (17)0.0812 (7)
H110.2754520.6449770.1218730.097*
C120.2524 (3)0.4914 (2)0.07792 (17)0.0807 (8)
H120.1412570.5187820.0701600.097*
C130.3439 (3)0.3710 (2)0.05816 (13)0.0617 (5)
C141.1475 (3)0.3641 (2)0.21491 (15)0.0709 (6)
H14A1.0883470.4286390.1770220.106*
H14B1.2142840.3004010.1852700.106*
H14C1.2140750.3907650.2490100.106*
C151.0301 (3)0.32062 (18)0.26768 (13)0.0569 (5)
H15A0.9666680.2900420.2333920.068*
H15B0.9567110.3867220.2939400.068*
C161.1186 (2)0.22276 (17)0.33334 (12)0.0511 (4)
H16A1.2015700.1614690.3074280.061*
H16B1.1713320.2562380.3714170.061*
C171.0083 (2)0.16814 (14)0.37936 (10)0.0405 (3)
C180.8495 (2)0.06328 (15)0.40943 (10)0.0417 (4)
H180.7927470.0102520.4052260.050*
C190.8449 (2)0.12661 (15)0.47331 (10)0.0447 (4)
H190.7854830.1257390.5209790.054*
C200.9816 (2)0.27071 (16)0.50929 (12)0.0536 (5)
H20A0.9850750.2355560.5650780.064*
H20B1.0875530.2767190.4963110.064*
C210.7390 (2)0.43804 (16)0.55381 (11)0.0475 (4)
C220.6787 (3)0.55602 (17)0.52184 (14)0.0575 (5)
C230.5467 (3)0.6358 (2)0.5584 (2)0.0803 (8)
H230.5058440.7149340.5378550.096*
C240.4807 (3)0.5938 (3)0.6245 (2)0.0887 (9)
H240.3924010.6448270.6496750.106*
C250.5424 (3)0.4749 (3)0.65591 (16)0.0820 (7)
H250.4935010.4496170.7016080.098*
C260.6724 (3)0.3939 (2)0.62204 (13)0.0643 (5)
H260.7128500.3151250.6432690.077*
C270.9908 (2)0.22528 (15)0.24068 (10)0.0427 (4)
C280.9446 (3)0.33296 (17)0.26824 (15)0.0616 (5)
H28A1.0396520.3973580.2854110.092*
H28B0.8939570.3549330.2238260.092*
H28C0.8707770.3156070.3131400.092*
C291.3552 (2)0.10071 (17)0.28346 (13)0.0540 (5)
C301.5235 (3)0.1721 (2)0.2597 (2)0.0843 (8)
H30A1.5376430.2552540.2700810.126*
H30B1.6007170.1523080.2911650.126*
H30C1.5394110.1543030.2025260.126*
O1WA0.6070 (7)0.1409 (6)0.4459 (4)0.131 (2)0.5
H1WA0.5168780.1070670.4216760.196*0.5
H1WB0.6820980.1269070.4172750.196*0.5
O1WB0.5611 (12)0.0619 (8)0.4788 (7)0.221 (5)0.5
H1WC0.4616030.0391640.4658470.331*0.5
H1WD0.5859330.0033440.4932370.331*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04335 (14)0.04085 (13)0.03331 (13)0.01424 (10)0.00541 (9)0.00347 (9)
O10.0648 (8)0.0437 (6)0.0449 (7)0.0220 (6)0.0107 (6)0.0074 (5)
O20.1017 (12)0.0711 (10)0.0494 (8)0.0289 (9)0.0241 (8)0.0095 (7)
O30.0442 (7)0.0783 (9)0.0516 (8)0.0188 (7)0.0055 (6)0.0060 (7)
O40.0811 (12)0.1187 (15)0.0575 (10)0.0068 (11)0.0093 (9)0.0185 (10)
N10.0419 (7)0.0363 (7)0.0363 (7)0.0125 (6)0.0042 (6)0.0016 (5)
N20.0453 (7)0.0376 (7)0.0364 (7)0.0053 (6)0.0015 (6)0.0036 (5)
N30.0516 (9)0.0518 (9)0.0469 (8)0.0093 (7)0.0069 (7)0.0050 (7)
N40.0637 (11)0.0724 (12)0.0702 (12)0.0260 (10)0.0155 (9)0.0037 (9)
N50.0521 (10)0.0899 (14)0.0863 (14)0.0200 (10)0.0137 (10)0.0073 (11)
N60.0416 (7)0.0407 (7)0.0355 (7)0.0128 (6)0.0045 (6)0.0054 (5)
N70.0473 (8)0.0405 (7)0.0373 (7)0.0087 (6)0.0008 (6)0.0064 (6)
N80.0604 (9)0.0416 (8)0.0448 (8)0.0148 (7)0.0016 (7)0.0071 (6)
N90.0698 (11)0.0609 (10)0.0560 (10)0.0271 (9)0.0017 (8)0.0030 (8)
N100.0758 (12)0.0499 (10)0.0810 (13)0.0241 (9)0.0135 (10)0.0083 (9)
C10.0545 (12)0.1051 (19)0.0653 (14)0.0181 (13)0.0020 (10)0.0203 (13)
C20.0431 (10)0.0634 (12)0.0559 (11)0.0168 (9)0.0015 (8)0.0016 (9)
C30.0472 (10)0.0429 (9)0.0567 (11)0.0171 (8)0.0030 (8)0.0018 (8)
C40.0418 (8)0.0308 (7)0.0386 (8)0.0072 (6)0.0028 (7)0.0043 (6)
C50.0425 (9)0.0396 (8)0.0460 (9)0.0136 (7)0.0073 (7)0.0022 (7)
C60.0500 (10)0.0417 (9)0.0413 (9)0.0095 (7)0.0113 (7)0.0009 (7)
C70.0603 (11)0.0495 (10)0.0418 (9)0.0025 (9)0.0060 (8)0.0097 (8)
C80.0533 (10)0.0505 (10)0.0418 (9)0.0040 (8)0.0082 (8)0.0094 (8)
C90.0643 (12)0.0578 (12)0.0552 (12)0.0103 (10)0.0005 (10)0.0045 (9)
C100.0919 (18)0.0548 (12)0.0696 (15)0.0114 (12)0.0050 (13)0.0021 (11)
C110.0889 (18)0.0569 (13)0.0788 (17)0.0043 (13)0.0147 (14)0.0070 (12)
C120.0566 (13)0.0810 (17)0.0838 (17)0.0101 (12)0.0160 (12)0.0174 (14)
C130.0504 (11)0.0677 (13)0.0602 (12)0.0071 (10)0.0115 (9)0.0116 (10)
C140.0763 (15)0.0601 (13)0.0749 (15)0.0232 (11)0.0179 (12)0.0016 (11)
C150.0576 (11)0.0547 (11)0.0579 (12)0.0180 (9)0.0107 (9)0.0043 (9)
C160.0498 (10)0.0492 (10)0.0579 (11)0.0207 (8)0.0065 (8)0.0070 (8)
C170.0412 (8)0.0387 (8)0.0399 (9)0.0104 (7)0.0005 (7)0.0033 (7)
C180.0417 (8)0.0424 (8)0.0398 (8)0.0128 (7)0.0031 (7)0.0008 (7)
C190.0453 (9)0.0474 (9)0.0357 (8)0.0081 (8)0.0054 (7)0.0001 (7)
C200.0591 (11)0.0487 (10)0.0485 (10)0.0079 (9)0.0093 (8)0.0134 (8)
C210.0556 (10)0.0435 (9)0.0462 (9)0.0171 (8)0.0044 (8)0.0127 (7)
C220.0588 (11)0.0429 (10)0.0717 (13)0.0148 (9)0.0137 (10)0.0119 (9)
C230.0652 (14)0.0539 (13)0.117 (2)0.0054 (11)0.0170 (15)0.0306 (14)
C240.0666 (15)0.093 (2)0.108 (2)0.0155 (14)0.0076 (15)0.0582 (18)
C250.0803 (16)0.111 (2)0.0647 (15)0.0379 (16)0.0163 (13)0.0341 (14)
C260.0787 (15)0.0690 (13)0.0507 (11)0.0302 (12)0.0036 (10)0.0105 (10)
C270.0441 (9)0.0410 (9)0.0393 (9)0.0093 (7)0.0013 (7)0.0004 (7)
C280.0667 (13)0.0431 (10)0.0770 (14)0.0201 (9)0.0000 (11)0.0061 (9)
C290.0490 (10)0.0528 (11)0.0603 (12)0.0189 (9)0.0091 (9)0.0016 (9)
C300.0527 (13)0.0753 (16)0.112 (2)0.0080 (11)0.0152 (13)0.0079 (15)
O1WA0.116 (4)0.165 (5)0.112 (4)0.056 (4)0.037 (3)0.035 (4)
O1WB0.227 (10)0.203 (9)0.298 (12)0.147 (8)0.103 (8)0.106 (8)
Geometric parameters (Å, º) top
Zn1—O11.9603 (12)C9—C101.375 (3)
Zn1—O31.9617 (13)C10—H100.9300
Zn1—N12.0460 (13)C10—C111.382 (4)
Zn1—N62.0234 (13)C11—H110.9300
O1—C271.275 (2)C11—C121.354 (4)
O2—C271.221 (2)C12—H120.9300
O3—C291.259 (2)C12—C131.414 (3)
O4—C291.210 (3)C14—H14A0.9600
N1—C41.327 (2)C14—H14B0.9600
N1—C51.386 (2)C14—H14C0.9600
N2—C41.359 (2)C14—C151.515 (3)
N2—C61.385 (2)C15—H15A0.9700
N2—C71.461 (2)C15—H15B0.9700
N3—N41.360 (2)C15—C161.536 (3)
N3—C71.448 (2)C16—H16A0.9700
N3—C81.369 (2)C16—H16B0.9700
N4—N51.303 (3)C16—C171.487 (2)
N5—C131.375 (3)C18—H180.9300
N6—C171.323 (2)C18—C191.339 (2)
N6—C181.381 (2)C19—H190.9300
N7—C171.358 (2)C20—H20A0.9700
N7—C191.377 (2)C20—H20B0.9700
N7—C201.453 (2)C21—C221.393 (3)
N8—N91.360 (2)C21—C261.391 (3)
N8—C201.448 (2)C22—C231.400 (3)
N8—C211.358 (2)C23—H230.9300
N9—N101.293 (3)C23—C241.350 (4)
N10—C221.365 (3)C24—H240.9300
C1—H1A0.9600C24—C251.401 (4)
C1—H1B0.9600C25—H250.9300
C1—H1C0.9600C25—C261.375 (3)
C1—C21.495 (3)C26—H260.9300
C2—H2A0.9700C27—C281.498 (3)
C2—H2B0.9700C28—H28A0.9600
C2—C31.536 (3)C28—H28B0.9600
C3—H3A0.9700C28—H28C0.9600
C3—H3B0.9700C29—C301.506 (3)
C3—C41.481 (2)C30—H30A0.9600
C5—H50.9300C30—H30B0.9600
C5—C61.342 (3)C30—H30C0.9600
C6—H60.9300O1WA—H1WA0.8503
C7—H7A0.9700O1WA—H1WB0.8498
C7—H7B0.9700O1WB—O1WBi1.714 (17)
C8—C91.388 (3)O1WB—H1WC0.8502
C8—C131.388 (3)O1WB—H1WD0.8497
C9—H90.9300
O1—Zn1—O3114.54 (6)C13—C12—H12121.3
O1—Zn1—N1116.32 (6)N5—C13—C8109.01 (19)
O1—Zn1—N698.55 (5)N5—C13—C12131.4 (2)
O3—Zn1—N197.61 (6)C8—C13—C12119.6 (2)
O3—Zn1—N6116.53 (6)H14A—C14—H14B109.5
N6—Zn1—N1114.42 (5)H14A—C14—H14C109.5
C27—O1—Zn1115.14 (11)H14B—C14—H14C109.5
C29—O3—Zn1116.15 (12)C15—C14—H14A109.5
C4—N1—Zn1128.79 (11)C15—C14—H14B109.5
C4—N1—C5106.58 (13)C15—C14—H14C109.5
C5—N1—Zn1123.15 (11)C14—C15—H15A109.3
C4—N2—C6108.02 (14)C14—C15—H15B109.3
C4—N2—C7127.03 (16)C14—C15—C16111.55 (18)
C6—N2—C7124.43 (15)H15A—C15—H15B108.0
N4—N3—C7120.28 (17)C16—C15—H15A109.3
N4—N3—C8110.13 (16)C16—C15—H15B109.3
C8—N3—C7129.48 (18)C15—C16—H16A109.1
N5—N4—N3108.71 (18)C15—C16—H16B109.1
N4—N5—C13108.27 (19)H16A—C16—H16B107.8
C17—N6—Zn1128.88 (11)C17—C16—C15112.67 (16)
C17—N6—C18106.94 (14)C17—C16—H16A109.1
C18—N6—Zn1123.04 (11)C17—C16—H16B109.1
C17—N7—C19107.84 (14)N6—C17—N7109.36 (14)
C17—N7—C20127.45 (16)N6—C17—C16124.08 (15)
C19—N7—C20124.62 (15)N7—C17—C16126.52 (16)
N9—N8—C20119.81 (17)N6—C18—H18125.3
C21—N8—N9109.92 (16)C19—C18—N6109.36 (15)
C21—N8—C20130.03 (16)C19—C18—H18125.3
N10—N9—N8108.86 (17)N7—C19—H19126.8
N9—N10—C22108.55 (17)C18—C19—N7106.49 (15)
H1A—C1—H1B109.5C18—C19—H19126.8
H1A—C1—H1C109.5N7—C20—H20A109.0
H1B—C1—H1C109.5N7—C20—H20B109.0
C2—C1—H1A109.5N8—C20—N7112.73 (15)
C2—C1—H1B109.5N8—C20—H20A109.0
C2—C1—H1C109.5N8—C20—H20B109.0
C1—C2—H2A108.9H20A—C20—H20B107.8
C1—C2—H2B108.9N8—C21—C22103.92 (17)
C1—C2—C3113.31 (17)N8—C21—C26133.60 (19)
H2A—C2—H2B107.7C26—C21—C22122.5 (2)
C3—C2—H2A108.9N10—C22—C21108.75 (18)
C3—C2—H2B108.9N10—C22—C23130.9 (2)
C2—C3—H3A108.9C21—C22—C23120.4 (2)
C2—C3—H3B108.9C22—C23—H23121.2
H3A—C3—H3B107.7C24—C23—C22117.6 (2)
C4—C3—C2113.28 (15)C24—C23—H23121.2
C4—C3—H3A108.9C23—C24—H24119.3
C4—C3—H3B108.9C23—C24—C25121.4 (2)
N1—C4—N2109.54 (14)C25—C24—H24119.3
N1—C4—C3126.56 (15)C24—C25—H25118.6
N2—C4—C3123.88 (16)C26—C25—C24122.8 (3)
N1—C5—H5125.1C26—C25—H25118.6
C6—C5—N1109.85 (15)C21—C26—H26122.3
C6—C5—H5125.1C25—C26—C21115.4 (2)
N2—C6—H6127.0C25—C26—H26122.3
C5—C6—N2106.01 (15)O1—C27—C28116.36 (16)
C5—C6—H6127.0O2—C27—O1123.09 (17)
N2—C7—H7A108.8O2—C27—C28120.55 (18)
N2—C7—H7B108.8C27—C28—H28A109.5
N3—C7—N2113.63 (15)C27—C28—H28B109.5
N3—C7—H7A108.8C27—C28—H28C109.5
N3—C7—H7B108.8H28A—C28—H28B109.5
H7A—C7—H7B107.7H28A—C28—H28C109.5
N3—C8—C9133.38 (19)H28B—C28—H28C109.5
N3—C8—C13103.87 (19)O3—C29—C30117.3 (2)
C13—C8—C9122.74 (19)O4—C29—O3124.3 (2)
C8—C9—H9122.1O4—C29—C30118.4 (2)
C10—C9—C8115.7 (2)C29—C30—H30A109.5
C10—C9—H9122.1C29—C30—H30B109.5
C9—C10—H10118.7C29—C30—H30C109.5
C9—C10—C11122.6 (3)H30A—C30—H30B109.5
C11—C10—H10118.7H30A—C30—H30C109.5
C10—C11—H11119.1H30B—C30—H30C109.5
C12—C11—C10121.9 (2)H1WA—O1WA—H1WB109.5
C12—C11—H11119.1O1WBi—O1WB—H1WC63.3
C11—C12—H12121.3O1WBi—O1WB—H1WD51.8
C11—C12—C13117.4 (2)H1WC—O1WB—H1WD109.5
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1WA—H1WA···O4ii0.852.002.802 (6)156
O1WB—H1WD···O1WAi0.852.272.774 (11)118
O1WB—H1WC···O4iii0.852.473.782 (11)130
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x+2, y, z+1.
Bis(azido-κN1)bis[1-(1H-benzotriazol-1-ylmethyl)-2-propyl-1H-imidazole-κN3]zinc(II) (2) top
Crystal data top
[Zn(C13H15N5)2(N3)2]Z = 2
Mr = 632.03F(000) = 656
Triclinic, P1Dx = 1.442 Mg m3
a = 7.0870 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 13.7109 (7) ÅCell parameters from 5404 reflections
c = 15.2483 (8) Åθ = 4.2–70.5°
α = 84.360 (4)°µ = 1.57 mm1
β = 83.990 (4)°T = 293 K
γ = 82.531 (4)°0.16 × 0.14 × 0.07 mm
V = 1455.62 (12) Å3
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
5469 independent reflections
Radiation source: SuperNova (Cu) X-ray Source4707 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.018
Detector resolution: 15.9737 pixels mm-1θmax = 70.8°, θmin = 3.3°
ω scansh = 86
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1614
Tmin = 0.756, Tmax = 1.000l = 1818
10761 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3428P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5469 reflectionsΔρmax = 0.33 e Å3
390 parametersΔρmin = 0.32 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.70419 (4)0.53789 (2)0.20223 (2)0.04551 (10)
N11.1637 (3)1.00454 (15)0.11518 (16)0.0651 (5)
N21.1872 (3)0.91273 (15)0.14636 (13)0.0578 (5)
N31.2613 (2)0.85709 (12)0.07890 (11)0.0453 (4)
N41.1438 (2)0.69873 (11)0.09370 (10)0.0407 (3)
N50.8941 (2)0.62122 (11)0.13413 (11)0.0433 (4)
N61.3659 (3)0.10093 (15)0.41227 (16)0.0688 (5)
N71.2803 (3)0.11395 (15)0.34044 (15)0.0649 (5)
N81.0882 (3)0.12699 (12)0.36241 (12)0.0529 (4)
N90.9502 (2)0.24770 (12)0.25558 (11)0.0457 (4)
N100.8578 (2)0.40489 (12)0.22523 (11)0.0430 (3)
N110.5142 (3)0.51494 (15)0.12130 (16)0.0669 (5)
N120.4989 (2)0.43475 (15)0.10514 (12)0.0526 (4)
N130.4763 (3)0.35666 (17)0.08858 (15)0.0691 (6)
N140.5834 (3)0.60288 (17)0.30590 (15)0.0722 (6)
N150.5493 (3)0.68601 (17)0.30555 (13)0.0584 (5)
N160.5106 (4)0.7709 (2)0.3086 (2)0.0967 (8)
C11.2235 (3)1.01033 (16)0.02659 (18)0.0566 (5)
C21.2330 (4)1.09229 (19)0.0373 (2)0.0761 (8)
H21.19101.15620.02260.091*
C31.3051 (4)1.0742 (2)0.1205 (2)0.0840 (9)
H31.31371.12700.16340.101*
C41.3670 (4)0.9790 (2)0.14407 (19)0.0753 (8)
H41.41530.97010.20220.090*
C51.3590 (3)0.89772 (19)0.08402 (16)0.0579 (5)
H51.39990.83410.10000.070*
C61.2863 (3)0.91582 (15)0.00186 (14)0.0457 (4)
C71.3088 (3)0.75198 (15)0.09614 (14)0.0459 (4)
H7A1.35690.73800.15390.055*
H7B1.40940.72870.05230.055*
C81.0838 (3)0.67134 (15)0.01798 (13)0.0479 (4)
H81.13880.68320.03960.057*
C90.9298 (3)0.62414 (15)0.04329 (13)0.0467 (4)
H90.85870.59770.00560.056*
C101.0262 (3)0.66784 (13)0.16360 (12)0.0407 (4)
C111.0386 (3)0.68435 (15)0.25759 (13)0.0490 (5)
H11A0.91660.71710.28090.059*
H11B1.13390.72860.25980.059*
C121.0890 (4)0.59146 (17)0.31714 (15)0.0575 (5)
H12A0.99460.54660.31540.069*
H12B1.21240.55890.29540.069*
C131.0959 (4)0.6144 (2)0.41158 (16)0.0714 (7)
H13A1.19250.65680.41380.107*
H13B1.12550.55410.44780.107*
H13C0.97400.64680.43320.107*
C141.2288 (3)0.10467 (15)0.48389 (17)0.0562 (5)
C151.2477 (4)0.09222 (17)0.57507 (18)0.0679 (7)
H151.36700.08130.59690.081*
C161.0838 (5)0.09684 (17)0.63000 (18)0.0701 (7)
H161.09150.08870.69080.084*
C170.9036 (4)0.11353 (16)0.59767 (17)0.0660 (7)
H170.79520.11610.63780.079*
C180.8816 (3)0.12623 (15)0.50887 (16)0.0565 (5)
H180.76150.13720.48780.068*
C191.0491 (3)0.12171 (13)0.45204 (15)0.0496 (5)
C200.9620 (4)0.14498 (15)0.29246 (15)0.0556 (5)
H20A0.83550.12960.31560.067*
H20B1.00890.10200.24600.067*
C211.1010 (3)0.28671 (16)0.20563 (14)0.0529 (5)
H211.21930.25300.18800.063*
C221.0427 (3)0.38280 (15)0.18773 (14)0.0484 (5)
H221.11550.42780.15500.058*
C230.8043 (3)0.32145 (14)0.26582 (13)0.0428 (4)
C240.6169 (3)0.31379 (17)0.31750 (15)0.0546 (5)
H24A0.59750.24480.32870.066*
H24B0.51610.34680.28300.066*
C250.6036 (4)0.3592 (2)0.40479 (17)0.0713 (7)
H25A0.63140.42700.39380.086*
H25B0.69910.32340.44090.086*
C260.4072 (6)0.3574 (3)0.4551 (2)0.1116 (13)
H26A0.31070.38180.41600.167*
H26B0.39610.39840.50340.167*
H26C0.39070.29090.47770.167*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04149 (15)0.03957 (15)0.05500 (17)0.00964 (10)0.00147 (11)0.00185 (11)
N10.0456 (10)0.0582 (12)0.0950 (16)0.0105 (9)0.0003 (10)0.0259 (11)
N20.0458 (9)0.0670 (12)0.0638 (11)0.0167 (9)0.0074 (8)0.0220 (9)
N30.0376 (8)0.0466 (9)0.0527 (9)0.0130 (7)0.0029 (7)0.0068 (7)
N40.0381 (8)0.0402 (8)0.0439 (8)0.0094 (6)0.0004 (6)0.0012 (6)
N50.0452 (8)0.0399 (8)0.0460 (9)0.0140 (7)0.0010 (7)0.0023 (7)
N60.0573 (12)0.0595 (12)0.0855 (15)0.0012 (9)0.0056 (11)0.0048 (11)
N70.0606 (12)0.0565 (11)0.0714 (13)0.0003 (9)0.0051 (10)0.0042 (10)
N80.0563 (10)0.0415 (9)0.0576 (10)0.0011 (8)0.0028 (8)0.0026 (8)
N90.0518 (9)0.0391 (8)0.0446 (9)0.0042 (7)0.0009 (7)0.0008 (7)
N100.0396 (8)0.0420 (8)0.0463 (9)0.0065 (7)0.0004 (7)0.0000 (7)
N110.0643 (12)0.0502 (11)0.0880 (15)0.0027 (9)0.0276 (11)0.0010 (10)
N120.0351 (8)0.0681 (13)0.0536 (10)0.0076 (8)0.0005 (7)0.0016 (9)
N130.0638 (12)0.0699 (13)0.0772 (14)0.0227 (10)0.0096 (11)0.0228 (11)
N140.0778 (14)0.0676 (14)0.0677 (13)0.0166 (11)0.0245 (11)0.0111 (11)
N150.0394 (9)0.0760 (15)0.0590 (11)0.0048 (9)0.0014 (8)0.0109 (10)
N160.0883 (18)0.0708 (16)0.129 (2)0.0073 (14)0.0045 (17)0.0256 (16)
C10.0354 (10)0.0493 (12)0.0877 (17)0.0095 (9)0.0123 (10)0.0061 (11)
C20.0519 (13)0.0498 (13)0.130 (3)0.0126 (11)0.0324 (16)0.0093 (15)
C30.0673 (17)0.083 (2)0.103 (2)0.0295 (15)0.0342 (17)0.0384 (18)
C40.0595 (14)0.100 (2)0.0676 (16)0.0277 (15)0.0149 (12)0.0203 (15)
C50.0465 (11)0.0703 (15)0.0576 (13)0.0146 (10)0.0053 (10)0.0020 (11)
C60.0319 (9)0.0474 (11)0.0593 (12)0.0130 (8)0.0055 (8)0.0008 (9)
C70.0346 (9)0.0507 (11)0.0526 (11)0.0116 (8)0.0010 (8)0.0006 (9)
C80.0496 (11)0.0539 (11)0.0402 (10)0.0121 (9)0.0033 (8)0.0048 (8)
C90.0498 (11)0.0467 (11)0.0458 (10)0.0126 (9)0.0026 (8)0.0072 (8)
C100.0424 (10)0.0359 (9)0.0437 (10)0.0083 (7)0.0000 (8)0.0021 (7)
C110.0527 (11)0.0486 (11)0.0476 (11)0.0168 (9)0.0012 (9)0.0064 (9)
C120.0680 (14)0.0547 (12)0.0515 (12)0.0119 (11)0.0096 (10)0.0029 (10)
C130.0936 (19)0.0752 (17)0.0465 (12)0.0199 (15)0.0033 (12)0.0007 (11)
C140.0588 (13)0.0391 (10)0.0698 (14)0.0032 (9)0.0077 (11)0.0018 (9)
C150.0837 (18)0.0469 (12)0.0769 (17)0.0056 (12)0.0274 (14)0.0059 (11)
C160.106 (2)0.0439 (12)0.0609 (14)0.0028 (13)0.0126 (15)0.0104 (10)
C170.0870 (18)0.0396 (11)0.0665 (15)0.0005 (11)0.0112 (13)0.0087 (10)
C180.0611 (13)0.0360 (10)0.0693 (14)0.0003 (9)0.0000 (11)0.0031 (9)
C190.0604 (12)0.0284 (9)0.0588 (12)0.0020 (8)0.0062 (10)0.0012 (8)
C200.0686 (14)0.0378 (10)0.0604 (13)0.0057 (9)0.0093 (11)0.0016 (9)
C210.0460 (11)0.0562 (12)0.0512 (12)0.0015 (9)0.0067 (9)0.0004 (9)
C220.0428 (10)0.0496 (11)0.0502 (11)0.0082 (8)0.0041 (8)0.0028 (9)
C230.0441 (10)0.0431 (10)0.0417 (10)0.0092 (8)0.0031 (8)0.0020 (8)
C240.0497 (11)0.0552 (12)0.0570 (13)0.0118 (9)0.0038 (10)0.0021 (10)
C250.0887 (19)0.0650 (15)0.0566 (14)0.0118 (13)0.0109 (13)0.0020 (11)
C260.130 (3)0.091 (2)0.099 (2)0.011 (2)0.061 (2)0.0093 (19)
Geometric parameters (Å, º) top
Zn1—N52.0171 (15)C7—H7B0.9700
Zn1—N102.0177 (16)C8—H80.9300
Zn1—N111.993 (2)C8—C91.343 (3)
Zn1—N141.955 (2)C9—H90.9300
N1—N21.297 (3)C10—C111.486 (3)
N1—C11.371 (3)C11—H11A0.9700
N2—N31.361 (2)C11—H11B0.9700
N3—C61.367 (3)C11—C121.515 (3)
N3—C71.441 (3)C12—H12A0.9700
N4—C71.462 (2)C12—H12B0.9700
N4—C81.373 (3)C12—C131.511 (3)
N4—C101.352 (2)C13—H13A0.9600
N5—C91.379 (3)C13—H13B0.9600
N5—C101.337 (2)C13—H13C0.9600
N6—N71.293 (3)C14—C151.402 (4)
N6—C141.384 (3)C14—C191.393 (3)
N7—N81.361 (3)C15—H150.9300
N8—C191.362 (3)C15—C161.357 (4)
N8—C201.445 (3)C16—H160.9300
N9—C201.459 (3)C16—C171.400 (4)
N9—C211.381 (3)C17—H170.9300
N9—C231.357 (3)C17—C181.371 (4)
N10—C221.382 (2)C18—H180.9300
N10—C231.327 (2)C18—C191.393 (3)
N11—N121.171 (3)C20—H20A0.9700
N12—N131.158 (3)C20—H20B0.9700
N14—N151.134 (3)C21—H210.9300
N15—N161.165 (3)C21—C221.339 (3)
C1—C21.417 (4)C22—H220.9300
C1—C61.389 (3)C23—C241.482 (3)
C2—H20.9300C24—H24A0.9700
C2—C31.351 (5)C24—H24B0.9700
C3—H30.9300C24—C251.513 (3)
C3—C41.391 (5)C25—H25A0.9700
C4—H40.9300C25—H25B0.9700
C4—C51.374 (3)C25—C261.519 (4)
C5—H50.9300C26—H26A0.9600
C5—C61.390 (3)C26—H26B0.9600
C7—H7A0.9700C26—H26C0.9600
N5—Zn1—N10103.99 (6)C10—C11—C12114.76 (17)
N11—Zn1—N5108.56 (8)H11A—C11—H11B107.6
N11—Zn1—N10104.84 (7)C12—C11—H11A108.6
N14—Zn1—N5109.95 (8)C12—C11—H11B108.6
N14—Zn1—N10116.78 (9)C11—C12—H12A109.3
N14—Zn1—N11112.14 (10)C11—C12—H12B109.3
N2—N1—C1108.72 (19)H12A—C12—H12B108.0
N1—N2—N3108.36 (19)C13—C12—C11111.5 (2)
N2—N3—C6110.37 (17)C13—C12—H12A109.3
N2—N3—C7119.91 (17)C13—C12—H12B109.3
C6—N3—C7129.65 (17)C12—C13—H13A109.5
C8—N4—C7124.59 (16)C12—C13—H13B109.5
C10—N4—C7126.86 (16)C12—C13—H13C109.5
C10—N4—C8108.56 (15)H13A—C13—H13B109.5
C9—N5—Zn1122.32 (13)H13A—C13—H13C109.5
C10—N5—Zn1129.66 (13)H13B—C13—H13C109.5
C10—N5—C9107.12 (16)N6—C14—C15130.7 (2)
N7—N6—C14108.5 (2)N6—C14—C19108.4 (2)
N6—N7—N8108.8 (2)C19—C14—C15121.0 (2)
N7—N8—C19110.36 (19)C14—C15—H15121.5
N7—N8—C20118.88 (19)C16—C15—C14117.0 (3)
C19—N8—C20130.76 (19)C16—C15—H15121.5
C21—N9—C20122.76 (18)C15—C16—H16119.1
C23—N9—C20129.07 (18)C15—C16—C17121.9 (3)
C23—N9—C21108.09 (16)C17—C16—H16119.1
C22—N10—Zn1122.53 (13)C16—C17—H17118.9
C23—N10—Zn1130.13 (13)C18—C17—C16122.2 (3)
C23—N10—C22106.81 (16)C18—C17—H17118.9
N12—N11—Zn1120.43 (16)C17—C18—H18121.9
N13—N12—N11177.3 (2)C17—C18—C19116.2 (2)
N15—N14—Zn1122.67 (18)C19—C18—H18121.9
N14—N15—N16177.3 (3)N8—C19—C14104.0 (2)
N1—C1—C2131.5 (2)N8—C19—C18134.2 (2)
N1—C1—C6108.9 (2)C18—C19—C14121.7 (2)
C6—C1—C2119.5 (3)N8—C20—N9111.03 (17)
C1—C2—H2121.2N8—C20—H20A109.4
C3—C2—C1117.6 (3)N8—C20—H20B109.4
C3—C2—H2121.2N9—C20—H20A109.4
C2—C3—H3119.0N9—C20—H20B109.4
C2—C3—C4122.0 (3)H20A—C20—H20B108.0
C4—C3—H3119.0N9—C21—H21126.9
C3—C4—H4119.0C22—C21—N9106.17 (18)
C5—C4—C3122.0 (3)C22—C21—H21126.9
C5—C4—H4119.0N10—C22—H22125.2
C4—C5—H5121.8C21—C22—N10109.65 (18)
C4—C5—C6116.3 (3)C21—C22—H22125.2
C6—C5—H5121.8N9—C23—C24126.60 (18)
N3—C6—C1103.61 (19)N10—C23—N9109.27 (17)
N3—C6—C5133.8 (2)N10—C23—C24124.07 (18)
C1—C6—C5122.5 (2)C23—C24—H24A109.2
N3—C7—N4111.99 (15)C23—C24—H24B109.2
N3—C7—H7A109.2C23—C24—C25112.1 (2)
N3—C7—H7B109.2H24A—C24—H24B107.9
N4—C7—H7A109.2C25—C24—H24A109.2
N4—C7—H7B109.2C25—C24—H24B109.2
H7A—C7—H7B107.9C24—C25—H25A109.2
N4—C8—H8126.7C24—C25—H25B109.2
C9—C8—N4106.53 (17)C24—C25—C26112.1 (3)
C9—C8—H8126.7H25A—C25—H25B107.9
N5—C9—H9125.5C26—C25—H25A109.2
C8—C9—N5109.09 (18)C26—C25—H25B109.2
C8—C9—H9125.5C25—C26—H26A109.5
N4—C10—C11125.92 (17)C25—C26—H26B109.5
N5—C10—N4108.70 (16)C25—C26—H26C109.5
N5—C10—C11125.37 (17)H26A—C26—H26B109.5
C10—C11—H11A108.6H26A—C26—H26C109.5
C10—C11—H11B108.6H26B—C26—H26C109.5
Zn1—N5—C9—C8169.50 (14)C6—N3—C7—N497.6 (2)
Zn1—N5—C10—N4168.56 (13)C6—C1—C2—C30.5 (3)
Zn1—N5—C10—C1112.5 (3)C7—N3—C6—C1176.91 (18)
Zn1—N10—C22—C21172.60 (15)C7—N3—C6—C51.4 (3)
Zn1—N10—C23—N9172.12 (13)C7—N4—C8—C9179.78 (18)
Zn1—N10—C23—C2410.7 (3)C7—N4—C10—N5179.39 (17)
N1—N2—N3—C60.2 (2)C7—N4—C10—C111.7 (3)
N1—N2—N3—C7177.55 (16)C8—N4—C7—N383.9 (2)
N1—C1—C2—C3178.1 (2)C8—N4—C10—N50.3 (2)
N1—C1—C6—N30.4 (2)C8—N4—C10—C11178.60 (19)
N1—C1—C6—C5178.90 (18)C9—N5—C10—N40.6 (2)
N2—N1—C1—C2178.2 (2)C9—N5—C10—C11178.36 (19)
N2—N1—C1—C60.5 (2)C10—N4—C7—N396.5 (2)
N2—N3—C6—C10.1 (2)C10—N4—C8—C90.1 (2)
N2—N3—C6—C5178.4 (2)C10—N5—C9—C80.6 (2)
N2—N3—C7—N485.6 (2)C10—C11—C12—C13179.2 (2)
N4—C8—C9—N50.4 (2)C14—N6—N7—N80.4 (3)
N4—C10—C11—C12114.0 (2)C14—C15—C16—C170.2 (4)
N5—C10—C11—C1267.2 (3)C15—C14—C19—N8178.4 (2)
N6—N7—N8—C190.3 (2)C15—C14—C19—C180.6 (3)
N6—N7—N8—C20178.77 (18)C15—C16—C17—C180.0 (4)
N6—C14—C15—C16177.8 (2)C16—C17—C18—C190.0 (3)
N6—C14—C19—N80.2 (2)C17—C18—C19—N8177.4 (2)
N6—C14—C19—C18178.00 (19)C17—C18—C19—C140.3 (3)
N7—N6—C14—C15178.0 (2)C19—N8—C20—N999.6 (2)
N7—N6—C14—C190.4 (3)C19—C14—C15—C160.5 (3)
N7—N8—C19—C140.0 (2)C20—N8—C19—C14178.8 (2)
N7—N8—C19—C18177.4 (2)C20—N8—C19—C183.8 (4)
N7—N8—C20—N979.2 (2)C20—N9—C21—C22176.54 (19)
N9—C21—C22—N100.2 (2)C20—N9—C23—N10176.19 (19)
N9—C23—C24—C25104.2 (2)C20—N9—C23—C240.9 (3)
N10—C23—C24—C2572.5 (3)C21—N9—C20—N869.5 (3)
C1—N1—N2—N30.4 (2)C21—N9—C23—N100.6 (2)
C1—C2—C3—C40.6 (4)C21—N9—C23—C24177.7 (2)
C2—C1—C6—N3178.50 (18)C22—N10—C23—N90.4 (2)
C2—C1—C6—C50.0 (3)C22—N10—C23—C24177.60 (19)
C2—C3—C4—C50.2 (4)C23—N9—C20—N8106.8 (2)
C3—C4—C5—C60.3 (3)C23—N9—C21—C220.5 (2)
C4—C5—C6—N3177.6 (2)C23—N10—C22—C210.1 (2)
C4—C5—C6—C10.4 (3)C23—C24—C25—C26176.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···N13i0.972.553.436 (3)151
C17—H17···N16ii0.932.603.395 (4)144
C20—H20B···N1iii0.972.583.544 (3)173
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y1, z.
 

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