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Three photoluminescent complexes containing either ZnII or CdII have been synthesized and their structures determined. Bis[4-amino-3,5-bis­(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis­(dicyanamido-κN1)zinc(II), [Zn(C12H10N6)2(C2N3)2], (I), bis­[4-amino-3,5-bis­(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis­(dicyanamido-κN1)cadmium(II), [Cd(C12H10N6)2(C2N3)2], (II), and bis­[4-amino-3,5-bis­(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis­(tri­cyano­methanido-κN1)cadmium(II), [Cd(C12H10N6)2(C4N3)2], (III), all crystallize in the space group P\overline{1}, with the metal centres lying on centres of inversion, but neither analogues (I) and (II) nor CdII complexes (II) and (III) are isomorphous. A combination of N—H...N and C—H...N hydrogen bonds and π–π stacking inter­actions generates three-dimensional framework structures in (I) and (II), and a sheet structure in (III). The photoluminescence spectra of (I)–(III) indicate that the energies of the π–π* transitions in the coordinated triazole ligand are modified by minor changes of the ligand geometry associated with coordination to the metal centres.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011391/sk3666sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011391/sk3666Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011391/sk3666IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011391/sk3666IIIsup4.hkl
Contains datablock III

CCDC references: 1039282; 1039280; 1039281

Computing details top

For all structures, data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(dicyanamido-κN1)zinc(II) (I) top
Crystal data top
[Zn(C12H10N6)2(C2N3)2]Z = 1
Mr = 674.01F(000) = 344
Triclinic, P1Dx = 1.575 Mg m3
a = 8.4211 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5379 (12) ÅCell parameters from 3720 reflections
c = 9.7491 (12) Åθ = 2.2–29.0°
α = 83.531 (6)°µ = 0.92 mm1
β = 66.048 (4)°T = 296 K
γ = 85.922 (6)°Block, colourless
V = 710.78 (16) Å30.25 × 0.20 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
3716 independent reflections
Radiation source: fine-focus sealed tube2731 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 9.091 pixels mm-1θmax = 29.0°, θmin = 3.0°
φ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 128
Tmin = 0.791, Tmax = 0.895l = 1213
13438 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1896P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3716 reflectionsΔρmax = 0.72 e Å3
214 parametersΔρmin = 0.33 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50000.50000.50000.04045 (15)
N10.4959 (2)0.7099 (2)0.4169 (2)0.0399 (4)
N20.4040 (2)0.7887 (2)0.3461 (2)0.0404 (4)
C30.4821 (3)0.9105 (2)0.2965 (2)0.0371 (5)
N40.6213 (2)0.91108 (19)0.3346 (2)0.0365 (4)
C50.6253 (3)0.7839 (2)0.4110 (2)0.0361 (5)
N310.5021 (3)1.1478 (2)0.1787 (2)0.0462 (5)
C320.4236 (3)1.0238 (2)0.2106 (3)0.0390 (5)
C330.2939 (3)0.9958 (3)0.1648 (3)0.0433 (5)
H330.24190.90840.19100.052*
C340.2442 (3)1.1006 (3)0.0798 (3)0.0505 (6)
H340.15821.08530.04670.061*
C350.3246 (4)1.2285 (3)0.0446 (3)0.0554 (7)
H350.29391.30100.01290.067*
C360.4508 (4)1.2475 (3)0.0958 (3)0.0550 (7)
H360.50361.33460.07160.066*
N410.7445 (3)1.0182 (2)0.3006 (2)0.0481 (5)
H41A0.69881.09720.26050.058*
H41B0.84030.98620.21870.058*
N510.6971 (2)0.5930 (2)0.5503 (2)0.0381 (4)
C520.7390 (3)0.7255 (2)0.4858 (2)0.0372 (5)
C530.8705 (3)0.7967 (3)0.4976 (3)0.0460 (6)
H530.89950.88710.45020.055*
C540.9575 (3)0.7296 (3)0.5815 (3)0.0511 (6)
H541.04690.77440.59050.061*
C550.9111 (3)0.5969 (3)0.6514 (3)0.0510 (6)
H550.96580.55180.71080.061*
C560.7813 (3)0.5313 (3)0.6319 (3)0.0459 (6)
H560.75160.44040.67750.055*
N110.1643 (4)0.5921 (3)0.9902 (3)0.0752 (8)
C120.2311 (3)0.5779 (3)0.8451 (3)0.0460 (6)
N130.3017 (3)0.5464 (2)0.7253 (2)0.0506 (5)
C140.0802 (3)0.7104 (3)1.0423 (3)0.0478 (6)
N150.0100 (3)0.8017 (3)1.1071 (3)0.0663 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0410 (2)0.0411 (2)0.0436 (2)0.00772 (15)0.02016 (18)0.00485 (16)
N10.0385 (10)0.0442 (11)0.0415 (11)0.0072 (8)0.0192 (9)0.0055 (8)
N20.0374 (10)0.0429 (10)0.0435 (11)0.0057 (8)0.0181 (9)0.0038 (8)
C30.0333 (11)0.0412 (12)0.0351 (11)0.0029 (9)0.0097 (9)0.0112 (9)
N40.0297 (9)0.0394 (10)0.0393 (10)0.0047 (7)0.0102 (8)0.0114 (8)
C50.0320 (11)0.0409 (12)0.0342 (11)0.0047 (9)0.0097 (9)0.0110 (9)
N310.0428 (11)0.0402 (11)0.0521 (12)0.0003 (8)0.0136 (10)0.0121 (9)
C320.0353 (12)0.0411 (12)0.0357 (12)0.0015 (9)0.0074 (10)0.0123 (9)
C330.0410 (13)0.0436 (13)0.0442 (13)0.0001 (10)0.0148 (11)0.0092 (10)
C340.0510 (15)0.0540 (15)0.0480 (14)0.0081 (12)0.0208 (12)0.0129 (12)
C350.0576 (16)0.0480 (15)0.0553 (16)0.0134 (12)0.0193 (14)0.0060 (12)
C360.0538 (16)0.0365 (12)0.0654 (17)0.0011 (11)0.0143 (14)0.0065 (12)
N410.0411 (11)0.0428 (11)0.0605 (13)0.0130 (9)0.0185 (10)0.0052 (10)
N510.0349 (10)0.0461 (10)0.0359 (10)0.0006 (8)0.0148 (8)0.0139 (8)
C520.0318 (11)0.0467 (12)0.0328 (11)0.0020 (9)0.0096 (9)0.0152 (9)
C530.0382 (13)0.0567 (15)0.0439 (13)0.0097 (11)0.0130 (11)0.0161 (11)
C540.0362 (13)0.0755 (18)0.0482 (15)0.0050 (12)0.0197 (11)0.0199 (13)
C550.0429 (14)0.0699 (18)0.0470 (14)0.0055 (12)0.0233 (12)0.0162 (13)
C560.0424 (13)0.0555 (15)0.0425 (13)0.0031 (11)0.0184 (11)0.0130 (11)
N110.102 (2)0.0582 (15)0.0492 (14)0.0068 (14)0.0162 (14)0.0025 (12)
C120.0380 (13)0.0445 (13)0.0511 (16)0.0067 (10)0.0112 (12)0.0100 (11)
N130.0452 (12)0.0592 (13)0.0454 (13)0.0056 (10)0.0132 (10)0.0132 (10)
C140.0424 (13)0.0546 (15)0.0434 (14)0.0074 (11)0.0121 (11)0.0085 (12)
N150.0599 (15)0.0770 (17)0.0645 (16)0.0124 (13)0.0240 (13)0.0296 (14)
Geometric parameters (Å, º) top
Zn1—N1i2.0771 (19)C34—H340.9300
Zn1—N12.0772 (19)C35—C361.375 (4)
Zn1—N512.1800 (19)C35—H350.9300
Zn1—N51i2.1800 (19)C36—H360.9300
Zn1—N13i2.223 (2)N41—H41A0.9395
Zn1—N132.223 (2)N41—H41B0.9371
N1—C51.318 (3)N51—C561.332 (3)
N1—N21.369 (3)N51—C521.349 (3)
N2—C31.319 (3)C52—C531.389 (3)
C3—N41.366 (3)C53—C541.385 (4)
C3—C321.472 (3)C53—H530.9300
N4—C51.356 (3)C54—C551.371 (4)
N4—N411.423 (3)C54—H540.9300
C5—C521.469 (3)C55—C561.384 (4)
N31—C321.340 (3)C55—H550.9300
N31—C361.340 (3)C56—H560.9300
C32—C331.388 (3)N11—C121.313 (4)
C33—C341.377 (4)N11—C141.325 (4)
C33—H330.9300C12—N131.139 (3)
C34—C351.378 (4)C14—N151.120 (3)
N1i—Zn1—N1180.00 (12)C33—C34—C35118.6 (3)
N1i—Zn1—N51103.20 (7)C33—C34—H34120.7
N1—Zn1—N5176.80 (7)C35—C34—H34120.7
N1i—Zn1—N51i76.80 (7)C36—C35—C34119.1 (3)
N1—Zn1—N51i103.20 (7)C36—C35—H35120.5
N51—Zn1—N51i180.0C34—C35—H35120.5
N1i—Zn1—N13i91.26 (8)N31—C36—C35123.7 (2)
N1—Zn1—N13i88.74 (8)N31—C36—H36118.1
N51—Zn1—N13i90.42 (7)C35—C36—H36118.1
N51i—Zn1—N13i89.58 (7)N4—N41—H41A104.8
N1i—Zn1—N1388.74 (8)N4—N41—H41B103.0
N1—Zn1—N1391.26 (8)H41A—N41—H41B105.5
N51—Zn1—N1389.58 (7)C56—N51—C52118.5 (2)
N51i—Zn1—N1390.42 (7)C56—N51—Zn1126.87 (17)
N13i—Zn1—N13180.0C52—N51—Zn1114.59 (15)
C5—N1—N2109.48 (19)N51—C52—C53122.1 (2)
C5—N1—Zn1114.61 (16)N51—C52—C5112.19 (19)
N2—N1—Zn1135.19 (15)C53—C52—C5125.7 (2)
C3—N2—N1106.26 (18)C54—C53—C52118.3 (2)
N2—C3—N4109.8 (2)C54—C53—H53120.9
N2—C3—C32122.8 (2)C52—C53—H53120.9
N4—C3—C32127.4 (2)C55—C54—C53119.7 (2)
C5—N4—C3106.25 (18)C55—C54—H54120.2
C5—N4—N41124.68 (19)C53—C54—H54120.2
C3—N4—N41129.1 (2)C54—C55—C56118.8 (2)
N1—C5—N4108.2 (2)C54—C55—H55120.6
N1—C5—C52120.3 (2)C56—C55—H55120.6
N4—C5—C52131.5 (2)N51—C56—C55122.6 (2)
C32—N31—C36116.3 (2)N51—C56—H56118.7
N31—C32—C33123.8 (2)C55—C56—H56118.7
N31—C32—C3117.5 (2)C12—N11—C14120.5 (3)
C33—C32—C3118.7 (2)N13—C12—N11168.9 (3)
C34—C33—C32118.4 (2)C12—N13—Zn1165.0 (2)
C34—C33—H33120.8N15—C14—N11169.1 (3)
C32—C33—H33120.8
C5—N1—N2—C30.6 (2)C3—C32—C33—C34177.6 (2)
Zn1—N1—N2—C3168.76 (16)C32—C33—C34—C350.3 (4)
N1—N2—C3—N40.2 (2)C33—C34—C35—C360.2 (4)
N1—N2—C3—C32178.66 (19)C32—N31—C36—C350.3 (4)
N2—C3—N4—C50.3 (2)C34—C35—C36—N310.3 (4)
C32—C3—N4—C5179.1 (2)C56—N51—C52—C532.4 (3)
N2—C3—N4—N41178.0 (2)Zn1—N51—C52—C53175.45 (16)
C32—C3—N4—N410.7 (4)C56—N51—C52—C5174.99 (19)
N2—N1—C5—N40.8 (2)Zn1—N51—C52—C57.2 (2)
Zn1—N1—C5—N4170.96 (13)N1—C5—C52—N512.5 (3)
N2—N1—C5—C52176.91 (18)N4—C5—C52—N51179.6 (2)
Zn1—N1—C5—C5211.3 (3)N1—C5—C52—C53174.8 (2)
C3—N4—C5—N10.7 (2)N4—C5—C52—C532.4 (4)
N41—N4—C5—N1177.74 (19)N51—C52—C53—C541.6 (3)
C3—N4—C5—C52176.7 (2)C5—C52—C53—C54175.4 (2)
N41—N4—C5—C524.9 (4)C52—C53—C54—C550.6 (4)
C36—N31—C32—C330.9 (3)C53—C54—C55—C562.1 (4)
C36—N31—C32—C3177.7 (2)C52—N51—C56—C550.8 (3)
N2—C3—C32—N31173.7 (2)Zn1—N51—C56—C55176.68 (17)
N4—C3—C32—N317.7 (3)C54—C55—C56—N511.4 (4)
N2—C3—C32—C337.7 (3)C14—N11—C12—N13169.7 (13)
N4—C3—C32—C33171.0 (2)N11—C12—N13—Zn169.3 (18)
N31—C32—C33—C340.9 (3)C12—N11—C14—N15169.9 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41—H41A···N310.942.122.896 (2)139
N41—H41B···N15ii0.942.273.101 (3)148
C34—H34···N15iii0.932.563.357 (4)144
Symmetry codes: (ii) x+1, y, z1; (iii) x, y+2, z+1.
Bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(dicyanamido-κN1)cadmium(II) (II) top
Crystal data top
[Cd(C12H10N6)2(C2N3)2]Z = 1
Mr = 721.03F(000) = 362
Triclinic, P1Dx = 1.645 Mg m3
a = 8.7209 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.7949 (4) ÅCell parameters from 7093 reflections
c = 10.3490 (4) Åθ = 2.0–30.5°
α = 91.966 (2)°µ = 0.81 mm1
β = 94.945 (2)°T = 296 K
γ = 112.682 (2)°Block, colourless
V = 727.67 (6) Å30.18 × 0.16 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
4392 independent reflections
Radiation source: fine-focus sealed tube4028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 9.091 pixels mm-1θmax = 30.5°, θmin = 2.5°
φ & ω scansh = 128
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1212
Tmin = 0.835, Tmax = 0.908l = 1414
16382 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0298P)2 + 0.1878P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4392 reflectionsΔρmax = 0.74 e Å3
214 parametersΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.50000.50000.50000.03552 (7)
N10.42177 (18)0.49212 (16)0.28558 (13)0.0329 (3)
N20.35782 (18)0.58440 (16)0.21291 (13)0.0335 (3)
C30.30610 (19)0.50560 (18)0.09715 (15)0.0288 (3)
N40.33633 (16)0.36337 (15)0.09455 (12)0.0272 (2)
C50.41039 (19)0.36019 (18)0.21448 (15)0.0281 (3)
N310.19861 (18)0.48614 (18)0.12728 (14)0.0363 (3)
C320.22708 (19)0.56498 (19)0.00901 (15)0.0297 (3)
C330.1834 (2)0.6981 (2)0.01743 (17)0.0357 (3)
H330.20690.75080.10050.043*
C340.1048 (2)0.7505 (2)0.08193 (19)0.0404 (4)
H340.07530.84010.06730.049*
C350.0705 (2)0.6683 (2)0.20334 (19)0.0417 (4)
H350.01520.69960.27160.050*
C360.1201 (2)0.5384 (2)0.22148 (18)0.0424 (4)
H360.09770.48420.30390.051*
N410.29499 (19)0.23950 (18)0.00863 (14)0.0369 (3)
H41A0.26250.28340.07530.044*
H41B0.21240.14950.01420.044*
N510.54952 (18)0.28263 (17)0.38956 (14)0.0340 (3)
C520.48039 (19)0.24287 (19)0.26500 (16)0.0299 (3)
C530.4835 (2)0.1090 (2)0.19269 (18)0.0374 (4)
H530.43350.08260.10740.045*
C540.5630 (2)0.0149 (2)0.2505 (2)0.0451 (4)
H540.56590.07650.20450.054*
C550.6371 (2)0.0579 (2)0.3759 (2)0.0463 (4)
H550.69330.00210.41540.056*
C560.6270 (2)0.1914 (2)0.44211 (18)0.0422 (4)
H560.67640.21940.52750.051*
N111.0291 (2)0.8653 (3)0.38882 (19)0.0593 (5)
C120.8859 (2)0.7785 (2)0.42838 (18)0.0415 (4)
N130.7688 (2)0.6972 (2)0.47342 (19)0.0563 (5)
C141.0396 (2)0.9320 (2)0.27615 (18)0.0364 (4)
N151.0655 (2)0.9913 (2)0.17991 (19)0.0539 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04493 (11)0.03405 (10)0.02380 (9)0.01100 (7)0.00564 (7)0.00052 (6)
N10.0429 (8)0.0274 (6)0.0278 (6)0.0134 (6)0.0024 (6)0.0007 (5)
N20.0434 (8)0.0273 (6)0.0296 (6)0.0138 (6)0.0031 (6)0.0011 (5)
C30.0303 (7)0.0236 (7)0.0305 (7)0.0077 (6)0.0061 (6)0.0022 (6)
N40.0293 (6)0.0238 (6)0.0266 (6)0.0083 (5)0.0034 (5)0.0010 (5)
C50.0295 (7)0.0250 (7)0.0270 (7)0.0073 (6)0.0051 (6)0.0005 (5)
N310.0423 (8)0.0358 (7)0.0301 (7)0.0141 (6)0.0061 (6)0.0036 (6)
C320.0276 (7)0.0268 (7)0.0310 (7)0.0061 (6)0.0059 (6)0.0041 (6)
C330.0369 (8)0.0307 (8)0.0383 (9)0.0117 (7)0.0058 (7)0.0021 (7)
C340.0371 (9)0.0350 (9)0.0515 (10)0.0154 (7)0.0080 (8)0.0109 (8)
C350.0366 (9)0.0455 (10)0.0411 (9)0.0132 (8)0.0029 (7)0.0162 (8)
C360.0478 (10)0.0455 (10)0.0299 (8)0.0138 (8)0.0033 (7)0.0056 (7)
N410.0470 (8)0.0316 (7)0.0309 (7)0.0158 (6)0.0011 (6)0.0073 (5)
N510.0385 (7)0.0319 (7)0.0306 (7)0.0119 (6)0.0057 (6)0.0073 (5)
C520.0282 (7)0.0262 (7)0.0330 (8)0.0071 (6)0.0065 (6)0.0044 (6)
C530.0372 (8)0.0295 (8)0.0435 (9)0.0113 (7)0.0030 (7)0.0014 (7)
C540.0455 (10)0.0300 (8)0.0624 (12)0.0166 (8)0.0107 (9)0.0045 (8)
C550.0464 (10)0.0406 (10)0.0582 (12)0.0216 (8)0.0102 (9)0.0196 (9)
C560.0460 (10)0.0438 (10)0.0378 (9)0.0176 (8)0.0055 (8)0.0151 (8)
N110.0406 (9)0.0737 (13)0.0500 (10)0.0072 (9)0.0008 (8)0.0183 (9)
C120.0435 (10)0.0379 (9)0.0371 (9)0.0101 (8)0.0019 (7)0.0003 (7)
N130.0519 (10)0.0500 (10)0.0525 (10)0.0025 (8)0.0141 (8)0.0015 (8)
C140.0302 (8)0.0344 (8)0.0421 (9)0.0101 (7)0.0028 (7)0.0009 (7)
N150.0544 (10)0.0531 (10)0.0552 (10)0.0203 (8)0.0093 (8)0.0160 (8)
Geometric parameters (Å, º) top
Cd1—N12.2553 (13)C34—H340.9300
Cd1—N1i2.2553 (13)C35—C361.382 (3)
Cd1—N13i2.3638 (17)C35—H350.9300
Cd1—N132.3638 (17)C36—H360.9300
Cd1—N51i2.3915 (14)N41—H41A0.8802
Cd1—N512.3916 (14)N41—H41B0.8962
N1—C51.3182 (19)N51—C561.334 (2)
N1—N21.362 (2)N51—C521.349 (2)
N2—C31.314 (2)C52—C531.384 (2)
C3—N41.3741 (19)C53—C541.388 (3)
C3—C321.463 (2)C53—H530.9300
N4—C51.355 (2)C54—C551.370 (3)
N4—N411.4170 (17)C54—H540.9300
C5—C521.476 (2)C55—C561.375 (3)
N31—C361.337 (2)C55—H550.9300
N31—C321.341 (2)C56—H560.9300
C32—C331.390 (2)N11—C121.298 (3)
C33—C341.376 (3)N11—C141.318 (3)
C33—H330.9300C12—N131.145 (2)
C34—C351.377 (3)C14—N151.140 (2)
N1—Cd1—N1i180.00 (8)C33—C34—C35119.02 (17)
N1—Cd1—N13i89.71 (6)C33—C34—H34120.5
N1i—Cd1—N13i90.28 (6)C35—C34—H34120.5
N1—Cd1—N1390.29 (6)C34—C35—C36118.55 (17)
N1i—Cd1—N1389.72 (6)C34—C35—H35120.7
N13i—Cd1—N13180.0C36—C35—H35120.7
N1—Cd1—N51i108.93 (5)N31—C36—C35123.75 (17)
N1i—Cd1—N51i71.07 (5)N31—C36—H36118.1
N13i—Cd1—N51i92.62 (6)C35—C36—H36118.1
N13—Cd1—N51i87.38 (6)N4—N41—H41A103.6
N1—Cd1—N5171.07 (5)N4—N41—H41B107.3
N1i—Cd1—N51108.93 (5)H41A—N41—H41B112.6
N13i—Cd1—N5187.38 (6)C56—N51—C52118.14 (15)
N13—Cd1—N5192.62 (6)C56—N51—Cd1126.23 (12)
N51i—Cd1—N51180.00 (6)C52—N51—Cd1115.43 (11)
C5—N1—N2109.62 (13)N51—C52—C53122.14 (15)
C5—N1—Cd1116.37 (10)N51—C52—C5113.16 (14)
N2—N1—Cd1133.17 (10)C53—C52—C5124.64 (15)
C3—N2—N1106.59 (13)C52—C53—C54118.43 (17)
N2—C3—N4109.64 (14)C52—C53—H53120.8
N2—C3—C32123.20 (14)C54—C53—H53120.8
N4—C3—C32127.15 (14)C55—C54—C53119.45 (18)
C5—N4—C3105.99 (12)C55—C54—H54120.3
C5—N4—N41125.56 (13)C53—C54—H54120.3
C3—N4—N41128.42 (13)C54—C55—C56118.76 (17)
N1—C5—N4108.16 (13)C54—C55—H55120.6
N1—C5—C52121.74 (14)C56—C55—H55120.6
N4—C5—C52130.00 (14)N51—C56—C55123.05 (18)
C36—N31—C32116.81 (15)N51—C56—H56118.5
N31—C32—C33123.22 (15)C55—C56—H56118.5
N31—C32—C3117.94 (14)C12—N11—C14121.65 (18)
C33—C32—C3118.83 (14)N13—C12—N11172.8 (2)
C34—C33—C32118.61 (16)C12—N13—Cd1162.67 (17)
C34—C33—H33120.7N15—C14—N11172.9 (2)
C32—C33—H33120.7
C5—N1—N2—C30.58 (18)N31—C32—C33—C341.0 (2)
Cd1—N1—N2—C3168.22 (11)C3—C32—C33—C34178.17 (15)
N1—N2—C3—N40.06 (17)C32—C33—C34—C350.7 (2)
N1—N2—C3—C32179.23 (14)C33—C34—C35—C361.5 (3)
N2—C3—N4—C50.47 (17)C32—N31—C36—C351.0 (3)
C32—C3—N4—C5179.72 (14)C34—C35—C36—N310.7 (3)
N2—C3—N4—N41177.40 (14)C56—N51—C52—C531.9 (2)
C32—C3—N4—N411.9 (2)Cd1—N51—C52—C53173.28 (12)
N2—N1—C5—N40.88 (17)C56—N51—C52—C5175.39 (14)
Cd1—N1—C5—N4170.02 (9)Cd1—N51—C52—C59.43 (16)
N2—N1—C5—C52175.78 (13)N1—C5—C52—N512.1 (2)
Cd1—N1—C5—C5213.31 (19)N4—C5—C52—N51177.98 (15)
C3—N4—C5—N10.82 (16)N1—C5—C52—C53175.09 (15)
N41—N4—C5—N1177.13 (14)N4—C5—C52—C530.8 (3)
C3—N4—C5—C52175.47 (15)N51—C52—C53—C541.1 (2)
N41—N4—C5—C526.6 (2)C5—C52—C53—C54175.92 (15)
C36—N31—C32—C331.8 (2)C52—C53—C54—C550.7 (3)
C36—N31—C32—C3177.36 (14)C53—C54—C55—C561.6 (3)
N2—C3—C32—N31171.72 (15)C52—N51—C56—C551.0 (3)
N4—C3—C32—N319.1 (2)Cd1—N51—C56—C55173.60 (13)
N2—C3—C32—C339.1 (2)C54—C55—C56—N510.7 (3)
N4—C3—C32—C33170.10 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41—H41A···N310.882.142.886 (2)143
N41—H41B···N15ii0.902.383.190 (2)150
C34—H34···N15iii0.932.523.300 (3)142
Symmetry codes: (ii) x1, y1, z; (iii) x+1, y+2, z.
Bis[4-amino-3,5-bis(pyridin-2-yl)-1,2,4-triazole-κ2N1,N5]bis(tricyanomethanido-κN1)cadmium(II) (III) top
Crystal data top
[Cd(C12H10N6)2(C4N3)2]Z = 1
Mr = 769.07F(000) = 386
Triclinic, P1Dx = 1.525 Mg m3
a = 9.271 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.571 (5) ÅCell parameters from 5042 reflections
c = 10.156 (5) Åθ = 2.1–30.7°
α = 87.833 (5)°µ = 0.71 mm1
β = 68.383 (5)°T = 296 K
γ = 88.803 (5)°Plate, colourless
V = 837.2 (8) Å30.42 × 0.34 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
5040 independent reflections
Radiation source: fine-focus sealed tube4682 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 9.091 pixels mm-1θmax = 30.7°, θmin = 2.6°
φ & ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1313
Tmin = 0.789, Tmax = 0.893l = 1414
17569 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0292P)2 + 0.1701P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
5040 reflectionsΔρmax = 0.35 e Å3
232 parametersΔρmin = 0.27 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.50000.50000.50000.03593 (5)
N10.40227 (14)0.28256 (12)0.58927 (13)0.0370 (3)
N20.25756 (15)0.22441 (13)0.64461 (14)0.0397 (3)
C30.27462 (16)0.10046 (14)0.69908 (14)0.0329 (3)
N40.42789 (13)0.07716 (11)0.67750 (12)0.0311 (2)
C50.50407 (16)0.19435 (13)0.60928 (13)0.0309 (3)
N310.18341 (16)0.13123 (13)0.78425 (14)0.0394 (3)
C320.14578 (17)0.00371 (14)0.77116 (14)0.0341 (3)
C330.00545 (19)0.05402 (17)0.81991 (16)0.0418 (3)
H330.02660.14830.80920.050*
C340.1244 (2)0.0401 (2)0.88523 (18)0.0494 (4)
H340.22730.01020.91890.059*
C350.0876 (2)0.17915 (19)0.89937 (19)0.0512 (4)
H350.16520.24440.94230.061*
C360.0661 (2)0.21934 (17)0.84879 (18)0.0462 (4)
H360.08980.31280.86000.055*
N410.49708 (15)0.03943 (12)0.72259 (15)0.0418 (3)
H41A0.43380.10680.72920.050*
H41B0.49430.01710.80890.050*
N510.70511 (14)0.35659 (12)0.50000 (12)0.0345 (2)
C520.67068 (16)0.22782 (13)0.56142 (13)0.0315 (3)
C530.78406 (18)0.13841 (16)0.57522 (17)0.0421 (3)
H530.75840.05060.61920.051*
C540.93701 (19)0.18322 (19)0.52168 (18)0.0477 (4)
H541.01520.12570.53060.057*
C550.97249 (19)0.31293 (19)0.45552 (18)0.0468 (4)
H551.07470.34330.41720.056*
C560.85348 (19)0.39696 (17)0.44715 (17)0.0430 (3)
H560.87710.48500.40320.052*
C110.63172 (19)0.36077 (16)0.01038 (15)0.0408 (3)
C120.5809 (2)0.40430 (16)0.14978 (16)0.0426 (3)
N130.5399 (2)0.43872 (18)0.26415 (16)0.0622 (4)
C140.5511 (2)0.25687 (18)0.02763 (17)0.0472 (4)
N150.4882 (2)0.1709 (2)0.0598 (2)0.0783 (6)
C160.7657 (3)0.4184 (2)0.0923 (2)0.0644 (5)
N170.8755 (3)0.4637 (3)0.1762 (3)0.1235 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04851 (10)0.02405 (7)0.03407 (8)0.00161 (5)0.01430 (6)0.00277 (5)
N10.0365 (6)0.0297 (6)0.0452 (7)0.0007 (4)0.0160 (5)0.0068 (5)
N20.0369 (6)0.0337 (6)0.0489 (7)0.0009 (5)0.0169 (5)0.0071 (5)
C30.0363 (7)0.0304 (6)0.0335 (6)0.0011 (5)0.0146 (5)0.0005 (5)
N40.0367 (6)0.0244 (5)0.0340 (5)0.0002 (4)0.0156 (5)0.0024 (4)
C50.0379 (7)0.0243 (5)0.0314 (6)0.0005 (5)0.0141 (5)0.0017 (4)
N310.0465 (7)0.0311 (6)0.0426 (6)0.0060 (5)0.0186 (6)0.0000 (5)
C320.0406 (7)0.0333 (6)0.0309 (6)0.0051 (5)0.0161 (5)0.0002 (5)
C330.0435 (8)0.0412 (8)0.0407 (7)0.0009 (6)0.0155 (6)0.0006 (6)
C340.0393 (8)0.0595 (10)0.0469 (9)0.0059 (7)0.0128 (7)0.0021 (7)
C350.0509 (10)0.0517 (9)0.0491 (9)0.0197 (8)0.0158 (8)0.0032 (7)
C360.0563 (10)0.0350 (7)0.0494 (9)0.0117 (7)0.0216 (8)0.0022 (6)
N410.0471 (7)0.0269 (6)0.0553 (8)0.0006 (5)0.0244 (6)0.0106 (5)
N510.0390 (6)0.0283 (5)0.0346 (6)0.0027 (4)0.0115 (5)0.0000 (4)
C520.0363 (7)0.0288 (6)0.0289 (6)0.0005 (5)0.0115 (5)0.0010 (4)
C530.0423 (8)0.0374 (7)0.0469 (8)0.0028 (6)0.0175 (7)0.0057 (6)
C540.0386 (8)0.0539 (9)0.0523 (9)0.0059 (7)0.0193 (7)0.0001 (7)
C550.0359 (8)0.0561 (10)0.0470 (8)0.0075 (7)0.0129 (7)0.0038 (7)
C560.0446 (8)0.0378 (7)0.0431 (8)0.0084 (6)0.0116 (7)0.0002 (6)
C110.0489 (8)0.0375 (7)0.0334 (7)0.0022 (6)0.0118 (6)0.0010 (5)
C120.0537 (9)0.0364 (7)0.0391 (8)0.0011 (6)0.0188 (7)0.0003 (6)
N130.0859 (12)0.0604 (10)0.0409 (8)0.0005 (9)0.0234 (8)0.0084 (7)
C140.0524 (9)0.0510 (9)0.0350 (7)0.0049 (7)0.0122 (7)0.0018 (6)
N150.0819 (13)0.0873 (14)0.0624 (11)0.0315 (11)0.0198 (10)0.0154 (10)
C160.0743 (13)0.0511 (10)0.0521 (10)0.0179 (9)0.0037 (9)0.0044 (8)
N170.118 (2)0.1047 (19)0.0944 (17)0.0563 (16)0.0275 (15)0.0083 (14)
Geometric parameters (Å, º) top
Cd1—N1i2.3032 (15)C35—C361.376 (3)
Cd1—N12.3032 (15)C35—H350.9300
Cd1—N512.3219 (15)C36—H360.9300
Cd1—N51i2.3219 (15)N41—H41A0.8649
Cd1—N13i2.3797 (19)N41—H41B0.9012
Cd1—N132.3797 (19)N51—C561.339 (2)
N1—C51.3191 (18)N51—C521.3496 (18)
N1—N21.3702 (19)C52—C531.385 (2)
N2—C31.3211 (18)C53—C541.389 (2)
C3—N41.3703 (19)C53—H530.9300
C3—C321.473 (2)C54—C551.376 (3)
N4—C51.3604 (17)C54—H540.9300
N4—N411.4193 (16)C55—C561.378 (2)
C5—C521.477 (2)C55—H550.9300
N31—C361.340 (2)C56—H560.9300
N31—C321.3453 (19)C11—C121.395 (2)
C32—C331.386 (2)C11—C161.402 (2)
C33—C341.388 (2)C11—C141.403 (2)
C33—H330.9300C12—N131.140 (2)
C34—C351.382 (3)C14—N151.142 (2)
C34—H340.9300C16—N171.141 (3)
N1i—Cd1—N1180.00 (6)C35—C34—H34120.5
N1i—Cd1—N51108.14 (5)C33—C34—H34120.5
N1—Cd1—N5171.86 (5)C36—C35—C34118.82 (15)
N1i—Cd1—N51i71.86 (5)C36—C35—H35120.6
N1—Cd1—N51i108.14 (5)C34—C35—H35120.6
N51—Cd1—N51i180.0N31—C36—C35123.65 (16)
N1i—Cd1—N13i92.09 (6)N31—C36—H36118.2
N1—Cd1—N13i87.91 (6)C35—C36—H36118.2
N51—Cd1—N13i89.17 (5)N4—N41—H41A103.3
N51i—Cd1—N13i90.83 (5)N4—N41—H41B104.4
N1i—Cd1—N1387.91 (6)H41A—N41—H41B110.8
N1—Cd1—N1392.09 (6)C56—N51—C52118.96 (13)
N51—Cd1—N1390.83 (5)C56—N51—Cd1123.45 (10)
N51i—Cd1—N1389.17 (5)C52—N51—Cd1117.55 (10)
N13i—Cd1—N13180.0N51—C52—C53121.74 (13)
C5—N1—N2109.27 (12)N51—C52—C5113.38 (11)
C5—N1—Cd1114.58 (10)C53—C52—C5124.88 (13)
N2—N1—Cd1135.56 (9)C52—C53—C54118.35 (15)
C3—N2—N1106.46 (12)C52—C53—H53120.8
N2—C3—N4109.83 (12)C54—C53—H53120.8
N2—C3—C32123.99 (13)C55—C54—C53119.83 (15)
N4—C3—C32126.18 (12)C55—C54—H54120.1
C5—N4—C3105.95 (11)C53—C54—H54120.1
C5—N4—N41125.21 (12)C54—C55—C56118.62 (15)
C3—N4—N41128.75 (12)C54—C55—H55120.7
N1—C5—N4108.48 (12)C56—C55—H55120.7
N1—C5—C52122.00 (12)N51—C56—C55122.45 (15)
N4—C5—C52129.52 (12)N51—C56—H56118.8
C36—N31—C32116.86 (14)C55—C56—H56118.8
N31—C32—C33123.55 (14)C12—C11—C16120.23 (16)
N31—C32—C3116.92 (13)C12—C11—C14120.31 (15)
C33—C32—C3119.52 (13)C16—C11—C14119.45 (15)
C32—C33—C34118.16 (15)N13—C12—C11179.34 (19)
C32—C33—H33120.9C12—N13—Cd1169.75 (17)
C34—C33—H33120.9N15—C14—C11178.6 (2)
C35—C34—C33118.94 (17)N17—C16—C11179.2 (3)
C5—N1—N2—C30.54 (16)N31—C32—C33—C340.3 (2)
Cd1—N1—N2—C3169.83 (11)C3—C32—C33—C34178.93 (14)
N1—N2—C3—N41.04 (16)C32—C33—C34—C350.2 (2)
N1—N2—C3—C32179.22 (13)C33—C34—C35—C360.3 (3)
N2—C3—N4—C51.15 (15)C32—N31—C36—C350.9 (2)
C32—C3—N4—C5179.12 (13)C34—C35—C36—N310.9 (3)
N2—C3—N4—N41177.58 (13)C56—N51—C52—C532.1 (2)
C32—C3—N4—N412.7 (2)Cd1—N51—C52—C53175.53 (11)
N2—N1—C5—N40.17 (16)C56—N51—C52—C5177.38 (13)
Cd1—N1—C5—N4172.77 (8)Cd1—N51—C52—C54.96 (15)
N2—N1—C5—C52179.76 (12)N1—C5—C52—N511.57 (19)
Cd1—N1—C5—C527.16 (17)N4—C5—C52—N51178.35 (13)
C3—N4—C5—N10.79 (15)N1—C5—C52—C53177.92 (14)
N41—N4—C5—N1177.38 (12)N4—C5—C52—C532.2 (2)
C3—N4—C5—C52179.14 (13)N51—C52—C53—C541.1 (2)
N41—N4—C5—C522.5 (2)C5—C52—C53—C54178.35 (14)
C36—N31—C32—C330.2 (2)C52—C53—C54—C550.8 (3)
C36—N31—C32—C3179.47 (13)C53—C54—C55—C561.5 (3)
N2—C3—C32—N31161.22 (14)C52—N51—C56—C551.3 (2)
N4—C3—C32—N3118.5 (2)Cd1—N51—C56—C55176.20 (12)
N2—C3—C32—C3318.0 (2)C54—C55—C56—N510.5 (3)
N4—C3—C32—C33162.26 (14)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N41—H41A···N310.862.192.889 (3)137
N41—H41B···N15ii0.902.273.023 (3)141
C56—H56···N17iii0.932.623.230 (4)123
Symmetry codes: (ii) x, y, z+1; (iii) x+2, y+1, z.
Selected geometric parameters (Å, °) top
Parameter(I) (M = Zn; X = N)(II) (M = Cd; X = C)(III) (M = Cd; X = C)
M—N12.0772 (19)2.2553 (13)2.3032 (15)
M—N132.223 (2)2.3638 (17)2.3797 (19)
M—N512.1800 (19)2.3915 (14)2.3219 (15)
X11—C121.313 (4)1.298 (3)1.395 (2)
X11—C141.325 (4)1.318 (3)1.403 (2)
X11—C161.402 (2)
C12—N131.139 (3)1.145 (2)1.140 (2)
C14—N151.120 (3)1.140 (2)1.142 (2)
C16—N171.141 (3)
N1—M—N1391.26 (8)90.29 (6)92.09 (6)
N1—M—N5176.80 (7)71.07 (5)71.86 (5)
N13—M—N5189.58 (7)92.62 (6)90.83 (5)
C12—X11—C14120.5 (3)121.65 (18)120.31 (15)
C12—X11—C16120.13 (16)
C14—X11—C16119.45 (15)
X11—C12—N13168.9 (3)172.8 (2)179.34 (19)
X11—C14—N15169.1 (3)172.9 (2)178.6 (2)
X11—C16—N17179.2 (3)
N2—C3—C32—N31173.7 (2)171.72 (15)161.22 (14)
N1—C5—C52—N512.5 (3)2.1 (2)1.57 (19)
N2—N1—M—N13-96.37 (16)-90.8 (2)-93.03 (14)
Pyrazole/N31–C368.01 (12)9.01 (9)18.16 (8)
Pyrazole/N51–C566.93 (12)7.26 (9)7.03 (8)
N31–C36/N51–C565.38 (16)3.34 (12)16.17 (8)
Hydrogen bonds and short intermolecular contacts (Å, °) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N41—H41A···N310.942.122.896 (3)139
N41—H41B···N15i0.942.273.101 (3)140
C34—H34···N15ii0.932.563.357 (4)144
(II)N41—H41A···N310.882.142.886 (2)143
N41—H41B···N15iii0.902.383.190 (2)150
C34—H34···N15iv0.932.523.300 (3)142
(III)N41—H41A···N310.862.192.889 (3)137
N41—H41B···N15v0.902.273.023 (2)141
C56—H56···N17vi0.932.623.230 (4)123
Symmetry codes: (i) x+1, y, z-1; (ii) -x, -y+2, -z+1; (iii) x-1, y-1, z; (iv) -x+1, -y+2, -z; (v) x, y, z+1; (vi) -x+2, -y+1, -z.
 

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