Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Naphthalenedi­imides, a class of organic dyes with an expanded π-electron-deficient plane, have attracted considerable inter­est because of their photo­induced electron transfer from neutral organic moieties to stable anionic radicals. This makes them excellent candidates for organic linkers in the construction of photochromic coordination polymers. Such a photochromic two-dimensional coordination polymer has been prepared using N,N′-bis­(pyridin-4-ylmeth­yl)naphthalene-1,8:4,5-bis(dicarboximide) (DPMNI). In crystallization tubes, upon slow diffusion of an MeOH solution of cadmium perchlorate into a CHCl3 solution of DPMNI, the complex poly[[bis­[μ2-2,7-bis­(pyridin-4-ylmeth­yl)benzo[imn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone-κ2N:N′]bis­(perchlorato-κO)cadmium(II)] chloro­form tetra­solvate], {[Cd(C26H16N4O4)2(ClO4)2]·4CHCl3}n, (I), was obtained. The asymmetric unit contains one Cd2+ cation, two DPMNI ligands, two coordinated ClO4 anions and four CHCl3 solvent mol­ecules. Each Cd2+ cation is inter­connected by four DPMNI linkers to generate a neutral two-dimensional naphthalenedi­imide coordination network with all the ClO4 anions above or below this plane. Strong inter­laminar anion–π inter­actions between the coordinated ClO4 anions and the imide rings of an adjacent layer lead to a three-dimensional supra­molecular structure. Compound (I) exhibits reversible photochromic behaviour and photocontrolled tunable luminescence properties, which may originate from the photoinduced electron-transfer generation of radicals in the DPMNI ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017958/eg3231sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017958/eg3231Isup2.hkl
Contains datablock I

CCDC reference: 1811683

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[bis[µ2-2,7-bis(pyridine-4-ylmethyl)benzo[imn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone]bis(perchlorato)cadmium(II)] chloroform tetrasolvate] top
Crystal data top
[Cd(C26H16N4O4)2(ClO4)2]·4CHCl3F(000) = 1684
Mr = 1685.63Dx = 1.707 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 13.8485 (7) ÅCell parameters from 9390 reflections
b = 15.0536 (6) Åθ = 2.6–29.4°
c = 16.6819 (9) ŵ = 0.98 mm1
β = 109.395 (6)°T = 153 K
V = 3280.3 (3) Å3Block, yellow
Z = 20.28 × 0.16 × 0.06 mm
Data collection top
Rigaku Saturn 724 CCD area-detector
diffractometer
9441 reflections with I > 2σ(I)
ω scansRint = 0.041
Absorption correction: multi-scan
(RAPID-AUTO; Rigaku, 1998)
θmax = 26.4°, θmin = 2.7°
Tmin = 0.983, Tmax = 1.000h = 1617
26057 measured reflectionsk = 1813
11605 independent reflectionsl = 2020
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0495P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.78 e Å3
11605 reflectionsΔρmin = 0.43 e Å3
867 parametersAbsolute structure: Refined as an inversion twin
1 restraintAbsolute structure parameter: 0.48 (3)
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.

Refinement. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cd10.50334 (3)0.33181 (5)0.25408 (3)0.02399 (12)
Cl10.73523 (11)0.31696 (12)0.43672 (10)0.0290 (4)
Cl20.25955 (13)0.37010 (11)0.08334 (11)0.0302 (4)
Cl31.03183 (19)0.89307 (15)0.00229 (17)0.0704 (7)
Cl40.9881 (2)0.97417 (17)0.16328 (18)0.0739 (8)
Cl51.14047 (19)0.8347 (2)0.10730 (18)0.0873 (8)
Cl6A0.3679 (16)0.293 (2)0.6445 (10)0.067 (4)0.62 (8)
Cl6B0.3826 (13)0.323 (3)0.622 (4)0.068 (9)0.38 (8)
Cl70.4754 (2)0.27303 (19)0.51361 (16)0.0831 (9)
Cl80.57474 (17)0.23161 (18)0.68969 (15)0.0649 (7)
Cl90.6200 (2)0.3596 (2)0.9033 (2)0.1015 (12)
Cl100.4874 (2)0.41857 (16)0.99309 (15)0.0634 (6)
Cl110.43782 (18)0.45736 (17)0.81532 (14)0.0599 (6)
Cl120.01239 (17)0.71582 (15)0.69113 (16)0.0641 (6)
Cl130.15871 (19)0.8099 (2)0.55370 (19)0.0899 (9)
Cl140.0308 (2)0.89337 (17)0.64720 (18)0.0756 (7)
O10.8728 (4)0.7580 (4)0.2271 (3)0.0391 (13)
O20.6610 (3)0.6230 (3)0.0091 (3)0.0338 (12)
O31.2941 (3)0.6663 (3)0.0900 (3)0.0363 (12)
O41.0755 (4)0.5556 (3)0.1577 (3)0.0421 (13)
O50.3167 (3)0.5172 (4)0.6021 (3)0.0386 (13)
O60.1129 (4)0.6493 (4)0.3616 (3)0.0418 (13)
O70.1171 (4)0.4196 (4)0.7184 (3)0.0386 (12)
O80.3172 (3)0.5755 (3)0.4907 (3)0.0337 (12)
O90.6329 (3)0.2856 (3)0.3860 (3)0.0348 (12)
O100.7486 (4)0.4036 (3)0.4066 (3)0.0473 (14)
O110.8096 (4)0.2567 (3)0.4274 (3)0.0461 (14)
O120.7401 (4)0.3202 (4)0.5238 (3)0.0459 (12)
O130.3669 (4)0.3483 (4)0.1218 (3)0.0554 (17)
O140.2028 (4)0.3146 (3)0.1222 (3)0.0456 (13)
O150.2457 (4)0.4611 (3)0.1012 (4)0.0475 (14)
O160.2304 (4)0.3536 (3)0.0051 (3)0.0456 (15)
N10.5705 (4)0.4626 (4)0.2200 (4)0.0279 (13)
N20.7675 (4)0.6898 (4)0.1092 (3)0.0250 (13)
N31.1844 (4)0.6049 (4)0.0317 (4)0.0279 (13)
N41.4075 (4)0.7478 (4)0.1858 (3)0.0267 (13)
N50.4237 (4)0.4215 (4)0.3272 (4)0.0255 (13)
N60.2143 (4)0.5847 (4)0.4829 (4)0.0273 (14)
N70.2166 (4)0.4968 (3)0.6034 (4)0.0262 (13)
N80.4272 (4)0.7030 (4)0.7195 (4)0.0259 (13)
C10.5112 (5)0.5348 (5)0.1956 (4)0.0300 (17)
H10.44290.53270.19620.036*
C20.5454 (5)0.6118 (5)0.1697 (4)0.0275 (16)
H20.50090.66150.15350.033*
C30.6433 (5)0.6177 (4)0.1670 (4)0.0235 (15)
C40.7050 (5)0.5436 (5)0.1926 (5)0.0309 (17)
H40.77370.54500.19290.037*
C50.6667 (5)0.4673 (5)0.2177 (5)0.0288 (18)
H50.70970.41660.23380.035*
C60.6805 (5)0.7025 (5)0.1382 (5)0.0334 (18)
H6A0.62350.72890.09150.040*
H6B0.69980.74530.18600.040*
C70.7474 (5)0.6491 (5)0.0300 (4)0.0277 (16)
C80.8345 (5)0.6377 (4)0.0021 (4)0.0253 (15)
C90.9324 (5)0.6671 (4)0.0489 (4)0.0233 (15)
C100.9506 (5)0.7083 (4)0.1283 (4)0.0250 (15)
C110.8636 (5)0.7225 (5)0.1604 (4)0.0286 (16)
C121.0484 (5)0.7322 (5)0.1778 (5)0.0348 (18)
H121.05980.76170.23040.042*
C131.1309 (5)0.7127 (5)0.1498 (5)0.0346 (18)
H131.19820.72820.18470.041*
C141.1170 (5)0.6712 (5)0.0723 (4)0.0278 (16)
C151.0170 (5)0.6497 (4)0.0201 (4)0.0247 (15)
C160.9992 (5)0.6096 (4)0.0594 (4)0.0261 (15)
C170.9001 (5)0.5854 (4)0.1093 (4)0.0302 (16)
H170.88820.55990.16380.036*
C180.8194 (5)0.5987 (5)0.0794 (4)0.0304 (16)
H180.75250.58060.11300.036*
C191.2064 (5)0.6496 (5)0.0465 (5)0.0308 (17)
C201.0874 (5)0.5877 (4)0.0886 (5)0.0313 (17)
C211.2726 (5)0.5690 (5)0.0514 (5)0.0328 (17)
H21A1.25110.51470.08620.039*
H21B1.32630.55180.00240.039*
C221.3177 (5)0.6342 (5)0.0986 (5)0.0306 (17)
C231.4180 (5)0.6610 (5)0.0633 (4)0.0323 (17)
H231.45800.64140.00820.039*
C241.4606 (6)0.7174 (5)0.1095 (5)0.0352 (18)
H241.53030.73450.08510.042*
C251.3101 (6)0.7199 (5)0.2205 (5)0.039 (2)
H251.27220.73860.27650.047*
C261.2629 (5)0.6653 (6)0.1785 (5)0.042 (2)
H261.19310.64930.20440.051*
C270.4844 (5)0.4685 (4)0.3919 (4)0.0238 (15)
H270.55630.46040.40680.029*
C280.4497 (5)0.5279 (4)0.4384 (4)0.0266 (15)
H280.49680.55900.48450.032*
C290.3454 (5)0.5421 (4)0.4176 (4)0.0246 (15)
C300.2815 (5)0.4939 (5)0.3507 (5)0.0344 (18)
H300.20940.50150.33430.041*
C310.3226 (5)0.4342 (5)0.3075 (5)0.0302 (18)
H310.27730.40100.26200.036*
C320.3070 (5)0.6123 (5)0.4637 (5)0.0296 (16)
H32A0.36180.62700.51760.035*
H32B0.29120.66680.42850.035*
C330.2305 (5)0.5381 (4)0.5581 (4)0.0277 (16)
C340.1187 (5)0.6149 (5)0.4277 (5)0.0330 (17)
C350.0299 (5)0.5984 (4)0.4569 (4)0.0233 (15)
C360.0412 (5)0.5492 (4)0.5294 (4)0.0234 (15)
C370.1386 (5)0.5160 (5)0.5810 (4)0.0263 (16)
C380.1481 (5)0.4675 (5)0.6522 (5)0.0326 (17)
H380.21350.44640.68630.039*
C390.0605 (5)0.4483 (5)0.6757 (5)0.0318 (17)
H390.06710.41350.72480.038*
C400.0332 (5)0.4800 (4)0.6275 (4)0.0232 (15)
C410.0453 (5)0.5303 (4)0.5540 (4)0.0201 (14)
C420.1405 (5)0.5640 (4)0.5043 (4)0.0247 (15)
C430.1506 (5)0.6135 (5)0.4332 (4)0.0291 (16)
H430.21570.63650.40050.035*
C440.0645 (5)0.6303 (5)0.4083 (4)0.0316 (16)
H440.07160.66340.35820.038*
C450.1220 (5)0.4610 (4)0.6551 (5)0.0256 (16)
C460.2314 (5)0.5473 (4)0.5296 (5)0.0265 (17)
C470.3080 (5)0.4757 (5)0.6265 (5)0.0301 (16)
H47A0.29120.42770.66950.036*
H47B0.36300.45380.57550.036*
C480.2889 (5)0.6327 (5)0.6871 (5)0.0306 (17)
H480.22170.63690.68430.037*
C490.3322 (5)0.7024 (5)0.7165 (5)0.0332 (19)
H490.29140.75380.73600.040*
C500.4810 (5)0.6287 (5)0.6956 (4)0.0284 (16)
H500.54840.62690.69830.034*
C510.4447 (5)0.5541 (5)0.6671 (5)0.0316 (17)
H510.48580.50230.65140.038*
C520.3466 (5)0.5563 (4)0.6618 (4)0.0253 (15)
C531.0223 (7)0.8768 (6)0.1039 (6)0.057 (2)
H530.96810.83120.12900.068*
C540.4576 (5)0.2365 (6)0.6078 (5)0.0422 (19)
H540.43290.17380.59700.051*
C550.5375 (6)0.4452 (6)0.9124 (5)0.047 (2)
H550.57670.50210.92690.056*
C560.0290 (6)0.7952 (6)0.6085 (6)0.054 (2)
H560.00320.77070.56770.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0236 (2)0.0257 (2)0.0290 (2)0.00186 (19)0.01731 (17)0.0044 (2)
Cl10.0289 (8)0.0238 (10)0.0336 (9)0.0005 (7)0.0098 (7)0.0019 (8)
Cl20.0312 (9)0.0246 (9)0.0322 (10)0.0007 (7)0.0073 (7)0.0016 (7)
Cl30.0817 (18)0.0569 (15)0.0694 (16)0.0053 (12)0.0210 (13)0.0109 (12)
Cl40.0826 (18)0.0541 (15)0.0798 (18)0.0179 (13)0.0199 (14)0.0005 (13)
Cl50.0682 (16)0.099 (2)0.0953 (19)0.0359 (17)0.0283 (14)0.005 (2)
Cl6A0.065 (4)0.063 (7)0.073 (5)0.015 (5)0.022 (3)0.015 (4)
Cl6B0.046 (5)0.058 (12)0.097 (15)0.013 (6)0.021 (5)0.031 (12)
Cl70.113 (2)0.0781 (18)0.0525 (15)0.0222 (16)0.0203 (14)0.0166 (13)
Cl80.0493 (13)0.0854 (18)0.0520 (14)0.0036 (12)0.0062 (11)0.0085 (13)
Cl90.0739 (17)0.129 (3)0.099 (2)0.0483 (18)0.0253 (16)0.0238 (19)
Cl100.0974 (18)0.0519 (13)0.0501 (13)0.0142 (12)0.0368 (13)0.0099 (10)
Cl110.0703 (15)0.0655 (15)0.0407 (13)0.0020 (12)0.0140 (11)0.0017 (11)
Cl120.0591 (14)0.0521 (14)0.0696 (16)0.0045 (11)0.0061 (12)0.0040 (12)
Cl130.0652 (15)0.084 (2)0.094 (2)0.0235 (14)0.0089 (14)0.0117 (16)
Cl140.0806 (18)0.0626 (17)0.0848 (19)0.0098 (13)0.0290 (15)0.0086 (14)
O10.046 (3)0.043 (3)0.033 (3)0.001 (2)0.019 (2)0.009 (2)
O20.021 (3)0.043 (3)0.036 (3)0.009 (2)0.008 (2)0.003 (2)
O30.021 (3)0.043 (3)0.047 (3)0.003 (2)0.013 (2)0.006 (2)
O40.039 (3)0.052 (3)0.042 (3)0.008 (2)0.023 (3)0.013 (3)
O50.021 (3)0.044 (3)0.052 (3)0.004 (2)0.014 (2)0.003 (3)
O60.036 (3)0.056 (4)0.040 (3)0.004 (2)0.022 (2)0.011 (3)
O70.038 (3)0.046 (3)0.037 (3)0.004 (2)0.019 (2)0.013 (3)
O80.022 (3)0.039 (3)0.041 (3)0.000 (2)0.011 (2)0.006 (2)
O90.029 (3)0.045 (3)0.028 (3)0.003 (2)0.005 (2)0.003 (2)
O100.056 (4)0.031 (3)0.056 (4)0.008 (3)0.019 (3)0.011 (3)
O110.040 (3)0.044 (3)0.056 (4)0.016 (2)0.018 (3)0.003 (3)
O120.059 (3)0.050 (3)0.026 (2)0.010 (3)0.011 (2)0.002 (3)
O130.034 (3)0.089 (5)0.039 (3)0.019 (3)0.006 (2)0.001 (3)
O140.059 (3)0.031 (3)0.050 (3)0.016 (2)0.022 (3)0.008 (2)
O150.072 (4)0.022 (3)0.063 (4)0.011 (3)0.043 (3)0.008 (2)
O160.055 (3)0.047 (4)0.030 (3)0.010 (2)0.008 (2)0.002 (2)
N10.024 (3)0.037 (4)0.027 (3)0.003 (3)0.014 (3)0.000 (3)
N20.028 (3)0.025 (3)0.027 (3)0.002 (2)0.016 (3)0.002 (2)
N30.023 (3)0.033 (3)0.033 (3)0.001 (3)0.015 (3)0.007 (3)
N40.023 (3)0.032 (3)0.029 (3)0.002 (3)0.014 (3)0.008 (3)
N50.025 (3)0.028 (3)0.030 (3)0.004 (2)0.018 (3)0.005 (3)
N60.019 (3)0.032 (3)0.035 (3)0.002 (2)0.014 (3)0.010 (3)
N70.026 (3)0.021 (3)0.038 (3)0.001 (2)0.018 (3)0.001 (3)
N80.018 (3)0.036 (4)0.026 (3)0.001 (3)0.010 (2)0.003 (3)
C10.022 (4)0.034 (4)0.041 (4)0.001 (3)0.019 (3)0.002 (4)
C20.029 (4)0.030 (4)0.027 (4)0.001 (3)0.013 (3)0.005 (3)
C30.024 (4)0.027 (4)0.020 (3)0.003 (3)0.008 (3)0.002 (3)
C40.016 (4)0.043 (5)0.037 (4)0.004 (3)0.013 (3)0.005 (4)
C50.025 (4)0.031 (4)0.032 (4)0.007 (3)0.012 (3)0.010 (3)
C60.025 (4)0.035 (4)0.047 (5)0.004 (3)0.020 (3)0.002 (3)
C70.023 (4)0.030 (4)0.032 (4)0.003 (3)0.011 (3)0.008 (3)
C80.020 (3)0.029 (4)0.026 (4)0.002 (3)0.006 (3)0.007 (3)
C90.025 (4)0.022 (4)0.025 (4)0.000 (3)0.011 (3)0.009 (3)
C100.027 (4)0.023 (4)0.028 (4)0.004 (3)0.013 (3)0.001 (3)
C110.030 (4)0.027 (4)0.032 (4)0.002 (3)0.015 (3)0.002 (3)
C120.032 (4)0.042 (5)0.030 (4)0.016 (3)0.011 (3)0.009 (3)
C130.029 (4)0.043 (5)0.031 (4)0.009 (3)0.008 (3)0.001 (3)
C140.022 (4)0.029 (4)0.034 (4)0.004 (3)0.011 (3)0.004 (3)
C150.023 (4)0.020 (4)0.031 (4)0.002 (3)0.008 (3)0.004 (3)
C160.032 (4)0.024 (4)0.028 (4)0.003 (3)0.019 (3)0.008 (3)
C170.030 (4)0.035 (4)0.025 (4)0.008 (3)0.010 (3)0.005 (3)
C180.021 (4)0.035 (4)0.036 (4)0.007 (3)0.011 (3)0.000 (3)
C190.024 (4)0.028 (4)0.044 (4)0.001 (3)0.017 (3)0.010 (3)
C200.039 (4)0.026 (4)0.037 (4)0.002 (3)0.024 (4)0.007 (3)
C210.032 (4)0.031 (4)0.043 (5)0.007 (3)0.021 (4)0.012 (3)
C220.029 (4)0.032 (4)0.040 (4)0.006 (3)0.024 (3)0.001 (3)
C230.037 (4)0.035 (4)0.025 (4)0.002 (3)0.010 (3)0.007 (3)
C240.036 (4)0.035 (4)0.039 (4)0.004 (3)0.018 (3)0.000 (3)
C250.026 (4)0.054 (5)0.039 (5)0.000 (4)0.014 (3)0.018 (4)
C260.017 (4)0.057 (5)0.049 (5)0.003 (3)0.007 (3)0.025 (4)
C270.018 (3)0.028 (4)0.027 (4)0.001 (3)0.011 (3)0.003 (3)
C280.024 (4)0.025 (4)0.034 (4)0.000 (3)0.014 (3)0.002 (3)
C290.026 (4)0.024 (4)0.028 (4)0.005 (3)0.014 (3)0.007 (3)
C300.021 (4)0.045 (5)0.037 (4)0.000 (3)0.010 (3)0.008 (3)
C310.028 (4)0.031 (4)0.031 (4)0.004 (3)0.009 (3)0.009 (3)
C320.024 (4)0.031 (4)0.039 (4)0.003 (3)0.018 (3)0.007 (3)
C330.026 (4)0.024 (4)0.034 (4)0.005 (3)0.011 (3)0.004 (3)
C340.036 (4)0.029 (4)0.038 (4)0.001 (3)0.019 (4)0.003 (3)
C350.019 (4)0.024 (4)0.029 (4)0.001 (3)0.012 (3)0.005 (3)
C360.022 (4)0.026 (4)0.024 (4)0.001 (3)0.009 (3)0.006 (3)
C370.025 (4)0.029 (4)0.024 (4)0.009 (3)0.006 (3)0.001 (3)
C380.023 (4)0.037 (4)0.035 (4)0.006 (3)0.006 (3)0.005 (3)
C390.033 (4)0.034 (4)0.033 (4)0.001 (3)0.018 (3)0.005 (3)
C400.022 (4)0.017 (3)0.034 (4)0.000 (3)0.015 (3)0.007 (3)
C410.015 (3)0.025 (4)0.022 (3)0.002 (3)0.008 (3)0.004 (3)
C420.022 (4)0.026 (4)0.029 (4)0.002 (3)0.012 (3)0.006 (3)
C430.025 (4)0.035 (4)0.028 (4)0.005 (3)0.009 (3)0.003 (3)
C440.033 (4)0.038 (4)0.027 (4)0.009 (3)0.015 (3)0.002 (3)
C450.030 (4)0.014 (3)0.036 (4)0.001 (3)0.015 (3)0.006 (3)
C460.022 (4)0.027 (4)0.032 (4)0.000 (3)0.011 (3)0.008 (3)
C470.027 (4)0.029 (4)0.042 (4)0.002 (3)0.021 (3)0.000 (3)
C480.017 (4)0.036 (4)0.040 (4)0.001 (3)0.011 (3)0.006 (4)
C490.028 (4)0.034 (5)0.039 (5)0.002 (3)0.013 (4)0.009 (4)
C500.021 (4)0.036 (4)0.030 (4)0.001 (3)0.012 (3)0.004 (3)
C510.028 (4)0.029 (4)0.042 (5)0.000 (3)0.018 (3)0.004 (3)
C520.021 (4)0.031 (4)0.028 (4)0.001 (3)0.013 (3)0.003 (3)
C530.059 (6)0.042 (5)0.068 (6)0.001 (4)0.020 (5)0.021 (5)
C540.036 (4)0.043 (5)0.046 (5)0.001 (4)0.013 (4)0.005 (4)
C550.046 (5)0.045 (5)0.052 (5)0.002 (4)0.020 (4)0.013 (4)
C560.053 (5)0.052 (6)0.053 (5)0.020 (4)0.011 (4)0.002 (4)
Geometric parameters (Å, º) top
Cd1—N4i2.314 (5)C9—C151.430 (9)
Cd1—N8ii2.318 (6)C10—C121.380 (9)
Cd1—N12.326 (6)C10—C111.487 (9)
Cd1—N52.328 (5)C12—C131.401 (10)
Cd1—O132.395 (5)C12—H120.9500
Cd1—O92.434 (4)C13—C141.390 (10)
Cl1—O111.420 (5)C13—H130.9500
Cl1—O121.432 (5)C14—C151.406 (9)
Cl1—O101.432 (5)C14—C191.475 (9)
Cl1—O91.467 (5)C15—C161.404 (9)
Cl2—O161.415 (5)C16—C171.396 (9)
Cl2—O151.428 (5)C16—C201.494 (9)
Cl2—O141.440 (5)C17—C181.382 (9)
Cl2—O131.447 (5)C17—H170.9500
Cl3—C531.750 (9)C18—H180.9500
Cl4—C531.744 (10)C21—C221.517 (9)
Cl5—C531.773 (9)C21—H21A0.9900
Cl6A—C541.772 (15)C21—H21B0.9900
Cl6B—C541.734 (19)C22—C231.376 (9)
Cl7—C541.757 (8)C22—C261.379 (10)
Cl8—C541.741 (7)C23—C241.402 (10)
Cl9—C551.762 (8)C23—H230.9500
Cl10—C551.754 (9)C24—H240.9500
Cl11—C551.754 (8)C25—C261.378 (10)
Cl12—C561.781 (9)C25—H250.9500
Cl13—C561.738 (8)C26—H260.9500
Cl14—C561.712 (9)C27—C281.371 (9)
O1—C111.202 (8)C27—H270.9500
O2—C71.222 (7)C28—C291.386 (8)
O3—C191.216 (8)C28—H280.9500
O4—C201.209 (8)C29—C301.378 (9)
O5—C331.218 (7)C29—C321.504 (9)
O6—C341.196 (8)C30—C311.387 (10)
O7—C451.208 (8)C30—H300.9500
O8—C461.226 (8)C31—H310.9500
N1—C11.342 (9)C32—H32A0.9900
N1—C51.348 (8)C32—H32B0.9900
N2—C71.398 (8)C33—C371.483 (9)
N2—C111.410 (8)C34—C351.487 (9)
N2—C61.453 (8)C35—C441.376 (9)
N3—C201.388 (9)C35—C361.383 (9)
N3—C191.409 (9)C36—C411.418 (8)
N3—C211.469 (8)C36—C371.428 (9)
N4—C241.321 (8)C37—C381.362 (10)
N4—C251.347 (9)C38—C391.424 (9)
N4—Cd1iii2.314 (5)C38—H380.9500
N5—C271.330 (8)C39—C401.365 (9)
N5—C311.341 (8)C39—H390.9500
N6—C331.389 (9)C40—C411.404 (9)
N6—C341.413 (9)C40—C451.477 (9)
N6—C321.481 (8)C41—C421.398 (9)
N7—C461.402 (9)C42—C431.369 (9)
N7—C451.414 (8)C42—C461.475 (9)
N7—C471.476 (8)C43—C441.410 (9)
N8—C501.330 (9)C43—H430.9500
N8—C491.333 (8)C44—H440.9500
N8—Cd1iv2.318 (6)C47—C521.521 (9)
C1—C21.374 (10)C47—H47A0.9900
C1—H10.9500C47—H47B0.9900
C2—C31.374 (9)C48—C491.377 (10)
C2—H20.9500C48—C521.385 (9)
C3—C41.383 (9)C48—H480.9500
C3—C61.513 (9)C49—H490.9500
C4—C51.387 (10)C50—C511.377 (10)
C4—H40.9500C50—H500.9500
C5—H50.9500C51—C521.390 (9)
C6—H6A0.9900C51—H510.9500
C6—H6B0.9900C53—H531.0000
C7—C81.483 (9)C54—H541.0000
C8—C181.368 (9)C55—H551.0000
C8—C91.412 (9)C56—H561.0000
C9—C101.407 (9)
N4i—Cd1—N8ii89.26 (19)C26—C22—C21122.2 (7)
N4i—Cd1—N191.2 (2)C22—C23—C24119.4 (7)
N8ii—Cd1—N1176.3 (2)C22—C23—H23120.3
N4i—Cd1—N5176.2 (2)C24—C23—H23120.3
N8ii—Cd1—N593.5 (2)N4—C24—C23122.6 (7)
N1—Cd1—N586.24 (19)N4—C24—H24118.7
N4i—Cd1—O1389.40 (19)C23—C24—H24118.7
N8ii—Cd1—O1389.5 (2)N4—C25—C26123.0 (7)
N1—Cd1—O1386.8 (2)N4—C25—H25118.5
N5—Cd1—O1393.26 (19)C26—C25—H25118.5
N4i—Cd1—O986.30 (18)C25—C26—C22119.5 (7)
N8ii—Cd1—O980.46 (18)C25—C26—H26120.2
N1—Cd1—O9103.20 (18)C22—C26—H26120.2
N5—Cd1—O991.55 (18)N5—C27—C28124.1 (6)
O13—Cd1—O9169.16 (18)N5—C27—H27118.0
O11—Cl1—O12109.9 (3)C28—C27—H27118.0
O11—Cl1—O10111.1 (3)C27—C28—C29119.4 (6)
O12—Cl1—O10111.0 (3)C27—C28—H28120.3
O11—Cl1—O9109.2 (3)C29—C28—H28120.3
O12—Cl1—O9107.9 (3)C30—C29—C28117.2 (6)
O10—Cl1—O9107.7 (3)C30—C29—C32122.9 (6)
O16—Cl2—O15112.0 (3)C28—C29—C32119.8 (6)
O16—Cl2—O14111.0 (3)C29—C30—C31119.9 (6)
O15—Cl2—O14109.4 (3)C29—C30—H30120.1
O16—Cl2—O13108.5 (3)C31—C30—H30120.1
O15—Cl2—O13108.3 (4)N5—C31—C30122.7 (7)
O14—Cl2—O13107.6 (3)N5—C31—H31118.7
Cl1—O9—Cd1135.2 (3)C30—C31—H31118.7
Cl2—O13—Cd1144.3 (3)N6—C32—C29113.0 (5)
C1—N1—C5117.3 (6)N6—C32—H32A109.0
C1—N1—Cd1120.4 (4)C29—C32—H32A109.0
C5—N1—Cd1122.1 (5)N6—C32—H32B109.0
C7—N2—C11125.3 (5)C29—C32—H32B109.0
C7—N2—C6116.5 (5)H32A—C32—H32B107.8
C11—N2—C6118.2 (6)O5—C33—N6120.5 (6)
C20—N3—C19125.8 (6)O5—C33—C37122.7 (6)
C20—N3—C21117.8 (6)N6—C33—C37116.8 (6)
C19—N3—C21116.3 (5)O6—C34—N6120.1 (6)
C24—N4—C25117.6 (6)O6—C34—C35124.4 (7)
C24—N4—Cd1iii116.5 (4)N6—C34—C35115.5 (6)
C25—N4—Cd1iii125.5 (5)C44—C35—C36120.8 (6)
C27—N5—C31116.8 (6)C44—C35—C34118.4 (6)
C27—N5—Cd1116.9 (4)C36—C35—C34120.7 (6)
C31—N5—Cd1126.3 (5)C35—C36—C41119.9 (6)
C33—N6—C34125.9 (6)C35—C36—C37121.6 (6)
C33—N6—C32116.4 (5)C41—C36—C37118.4 (6)
C34—N6—C32117.4 (6)C38—C37—C36120.8 (6)
C46—N7—C45125.3 (6)C38—C37—C33120.1 (6)
C46—N7—C47117.3 (5)C36—C37—C33119.1 (6)
C45—N7—C47117.4 (6)C37—C38—C39120.3 (7)
C50—N8—C49116.3 (6)C37—C38—H38119.9
C50—N8—Cd1iv121.1 (4)C39—C38—H38119.9
C49—N8—Cd1iv122.0 (5)C40—C39—C38119.8 (7)
N1—C1—C2122.6 (6)C40—C39—H39120.1
N1—C1—H1118.7C38—C39—H39120.1
C2—C1—H1118.7C39—C40—C41121.2 (6)
C1—C2—C3120.8 (6)C39—C40—C45118.4 (6)
C1—C2—H2119.6C41—C40—C45120.4 (6)
C3—C2—H2119.6C42—C41—C40121.9 (5)
C2—C3—C4116.9 (6)C42—C41—C36118.5 (6)
C2—C3—C6120.6 (6)C40—C41—C36119.6 (6)
C4—C3—C6122.5 (6)C43—C42—C41121.0 (6)
C3—C4—C5120.1 (6)C43—C42—C46119.3 (6)
C3—C4—H4119.9C41—C42—C46119.6 (6)
C5—C4—H4119.9C42—C43—C44120.0 (6)
N1—C5—C4122.3 (7)C42—C43—H43120.0
N1—C5—H5118.9C44—C43—H43120.0
C4—C5—H5118.9C35—C44—C43119.6 (6)
N2—C6—C3113.7 (6)C35—C44—H44120.2
N2—C6—H6A108.8C43—C44—H44120.2
C3—C6—H6A108.8O7—C45—N7120.1 (6)
N2—C6—H6B108.8O7—C45—C40124.1 (6)
C3—C6—H6B108.8N7—C45—C40115.8 (6)
H6A—C6—H6B107.7O8—C46—N7119.0 (6)
O2—C7—N2119.8 (6)O8—C46—C42124.0 (7)
O2—C7—C8122.7 (6)N7—C46—C42117.0 (6)
N2—C7—C8117.5 (5)N7—C47—C52111.8 (5)
C18—C8—C9121.2 (6)N7—C47—H47A109.3
C18—C8—C7120.1 (6)C52—C47—H47A109.3
C9—C8—C7118.6 (6)N7—C47—H47B109.3
C10—C9—C8122.8 (6)C52—C47—H47B109.3
C10—C9—C15119.1 (6)H47A—C47—H47B107.9
C8—C9—C15118.0 (6)C49—C48—C52117.8 (6)
C12—C10—C9120.7 (6)C49—C48—H48121.1
C12—C10—C11120.0 (6)C52—C48—H48121.1
C9—C10—C11119.3 (6)N8—C49—C48124.8 (7)
O1—C11—N2120.3 (6)N8—C49—H49117.6
O1—C11—C10123.2 (6)C48—C49—H49117.6
N2—C11—C10116.5 (6)N8—C50—C51123.9 (6)
C10—C12—C13119.5 (7)N8—C50—H50118.1
C10—C12—H12120.2C51—C50—H50118.1
C13—C12—H12120.2C50—C51—C52118.6 (6)
C14—C13—C12121.9 (6)C50—C51—H51120.7
C14—C13—H13119.1C52—C51—H51120.7
C12—C13—H13119.1C48—C52—C51118.5 (6)
C13—C14—C15118.8 (6)C48—C52—C47122.6 (6)
C13—C14—C19119.9 (6)C51—C52—C47118.8 (6)
C15—C14—C19121.2 (6)Cl4—C53—Cl3111.8 (5)
C16—C15—C14120.8 (6)Cl4—C53—Cl5111.2 (5)
C16—C15—C9119.3 (6)Cl3—C53—Cl5108.8 (5)
C14—C15—C9119.9 (6)Cl4—C53—H53108.3
C17—C16—C15120.4 (6)Cl3—C53—H53108.3
C17—C16—C20119.8 (6)Cl5—C53—H53108.3
C15—C16—C20119.8 (6)Cl6B—C54—Cl8111.6 (9)
C18—C17—C16120.0 (6)Cl6B—C54—Cl799 (3)
C18—C17—H17120.0Cl8—C54—Cl7110.1 (4)
C16—C17—H17120.0Cl8—C54—Cl6A109.0 (6)
C8—C18—C17120.9 (6)Cl7—C54—Cl6A118.9 (11)
C8—C18—H18119.5Cl8—C54—H54106.0
C17—C18—H18119.5Cl7—C54—H54106.0
O3—C19—N3121.1 (6)Cl6A—C54—H54106.0
O3—C19—C14123.3 (7)Cl10—C55—Cl11110.0 (4)
N3—C19—C14115.5 (6)Cl10—C55—Cl9109.4 (5)
O4—C20—N3121.4 (6)Cl11—C55—Cl9109.3 (4)
O4—C20—C16122.0 (6)Cl10—C55—H55109.4
N3—C20—C16116.6 (6)Cl11—C55—H55109.4
N3—C21—C22113.2 (5)Cl9—C55—H55109.4
N3—C21—H21A108.9Cl14—C56—Cl13112.0 (5)
C22—C21—H21A108.9Cl14—C56—Cl12111.4 (5)
N3—C21—H21B108.9Cl13—C56—Cl12109.8 (5)
C22—C21—H21B108.9Cl14—C56—H56107.8
H21A—C21—H21B107.8Cl13—C56—H56107.8
C23—C22—C26117.8 (6)Cl12—C56—H56107.8
C23—C22—C21119.9 (7)
Symmetry codes: (i) x+2, y1/2, z; (ii) x, y1/2, z+1; (iii) x+2, y+1/2, z; (iv) x, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21B···O15v0.992.653.144 (8)111
C24—H24···O2v0.952.483.073 (9)120
C24—H24···O13iii0.952.433.155 (9)133
C25—H25···O11iii0.952.413.341 (9)168
C26—H26···O40.952.473.191 (9)133
C27—H27···O8v0.952.533.139 (8)122
C28—H28···O8v0.952.563.134 (8)120
C31—H31···O140.952.573.484 (9)162
C32—H32B···O12vi0.992.533.217 (9)127
C49—H49···O14iv0.952.453.179 (9)133
C50—H50···O5vii0.952.613.193 (9)120
C51—H51···O5vii0.952.593.165 (8)119
C53—H53···O14viii1.002.423.171 (10)131
C54—H54···O8ii1.002.313.199 (9)147
C55—H55···O2ix1.002.233.211 (10)166
C56—H56···O11vi1.002.573.336 (10)133
Symmetry codes: (ii) x, y1/2, z+1; (iii) x+2, y+1/2, z; (iv) x, y+1/2, z+1; (v) x+1, y, z; (vi) x+1, y+1/2, z+1; (vii) x1, y, z; (viii) x+1, y+1/2, z; (ix) x, y, z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds