metal-organic compounds
Bis(1,10-phenanthrolin-1-ium) tetrachloridozincate monohydrate
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bDepartment of Chemistry, Pondicherry University, Pondicherry 605 014, India
*Correspondence e-mail: a_sp59@yahoo.in
In the 12H9N2)2[ZnCl4]·H2O, the two independent 1,10-phenanthrolinium cations are bridged by the water molecule and the tetrahedral tetrachloridozincate anion via N—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming chains along [100]. The chains are linked via C—H⋯Cl hydrogen bonds and a number of π–π interactions [centroid–centroid distances vary from 3.5594 (14) to 3.7057 (13) Å], forming a three-dimensional network. In each 1,10-phenanthrolinium cation, there is a short N—H⋯N interaction.
of the title compound, (CCCDC reference: 979772
Related literature
For an example of the ). For details of the Cambridge Structural Database, see: Allen (2002).
of a hybrid compound combining an organic cation and the tetrachloridozincate anion, see: Dong & Liu (2012Experimental
Crystal data
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 979772
10.1107/S1600536814000208/su2681sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000208/su2681Isup2.hkl
Zinc chloride (136 mg, 1 mmol) was dissolved in 10 mL of water. To this 1,10-phenanthroline (396 mg, 2 mmol) in 20 ml of an EtOH/HCl mixture (1:9 v/v) was added drop wise. The mixture was heated to 323 K for 2–3 hrs and then allowed to stand. On slow evaporation colourless crystals separated out. They were filtered off and recrystallized using acidified water.
The NH and water H atoms were located in a difference Fourier map and freely refined. The C bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C–H = 0.93 Å with Uiso(H) = 1.2Ueq(C).
As part of an ongoing investigation of the structures of and non-covalent interactions present in self-assembling organic and inorganic hybrid materials prepared by the combination of an organic cation and the tetrachloridozincate anion we synthesized the title compound. There are only a small number of structures of materials containing bis(1,10-phenanthrolinium) cations and perhalometallate anions in the Cambridge Structural Database (CSD; V5.35, last update Nov. 2013; Allen, 2002), and none of them involve the tetrachloridozincate anion.
The molecule structure of the title compound is shown in Fig. 1. The
contains one inorganic tetrachloridozincate anion and two 1,10-phenanthrolinium organic cations. The compound crystallized as a monohydrate. The tetrachlorozincate anion has a perfect tetrahedral coordination environment. The bond lengths Zn—Cl [2.556 (7) - 2.3085 (7) Å] and C—N [1.320 (3) - 1.362 (3) Å] are comparable with the values reported for Bis(10-methoxybenzo[h]quinolinium) tetrachloridozinc [Dong & Liu, 2012]. The sum of the bond angles around atoms N1 and N15 (360°) in the 1,10-phenanthrolinium cations indicates sp2 states. The two 1,10-phenanthrolinium ring systems (N1/N12/C2-C11/C13/C14) and (N15/N26/C16-C25/C27/C28) are planar with r.m.s values of 0.029 (3) and 0.022 (2) Å, respectively. In each 1,10-phenanthrolinium cation there is a short N-H···N interaction (Table 1).In the crystal, the two independent 1,10-phenanthrolinium cations are bridged by the water molecule and the tetrachloridozinc anion via N-H···O, O-H···Cl and N-H···Cl hydrogen bonds (Table 1 and Fig. 2) forming chains along [100]. The chains are linked via C-H···Cl hydrogen bonds (Table 1) and a number of π-π interactions forming a three-dimensional network.
The centroid-centroid distances are 3.5594 (14) Å for Cg1···Cg2i [Cg1 and Cg2 and the centroids of rings N1/C2-C5/C14 and N12/C8-C11/C13, respectively; symmetry code: (i) = -x, -y+2, -z+1 ], 3.6501 (15) Å for Cg1···Cg3i [Cg3 is the centroid of ring C5-C8/C13/C14] and 3.7057 (13) Å for Cg8···Cg9ii [Cg8 and Cg9 are the centroids of rings N26/C22-C25/C27 and C19-C22/C27/C28, respectively; symmetry code: (ii) -x, -y, -z+2].
For an example of the
of an inorganic hybrid compound combining an organic cation and the tetrachloridozincate anion, see: Dong & Liu (2012). For details of the Cambridge Structural Database, see: Allen (2002).Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at 30% probability level. | |
Fig. 2. A view along the b-axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). |
(C12H9N2)2[ZnCl4]·H2O | F(000) = 1192 |
Mr = 587.61 | Dx = 1.589 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 3414 reflections |
a = 14.6046 (5) Å | θ = 3.8–25.0° |
b = 10.8008 (3) Å | µ = 1.46 mm−1 |
c = 16.3151 (6) Å | T = 293 K |
β = 107.390 (4)° | Block, colourless |
V = 2455.93 (14) Å3 | 0.21 × 0.18 × 0.15 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with Eos detector | 4293 independent reflections |
Radiation source: fine-focus sealed tube | 3414 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scans | θmax = 25.0°, θmin = 3.8° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | h = −17→17 |
Tmin = 0.743, Tmax = 0.803 | k = −11→12 |
10373 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0278P)2 + 0.2557P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4293 reflections | Δρmax = 0.38 e Å−3 |
324 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0165 (5) |
(C12H9N2)2[ZnCl4]·H2O | V = 2455.93 (14) Å3 |
Mr = 587.61 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 14.6046 (5) Å | µ = 1.46 mm−1 |
b = 10.8008 (3) Å | T = 293 K |
c = 16.3151 (6) Å | 0.21 × 0.18 × 0.15 mm |
β = 107.390 (4)° |
Oxford Diffraction Xcalibur diffractometer with Eos detector | 4293 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 3414 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.803 | Rint = 0.028 |
10373 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.38 e Å−3 |
4293 reflections | Δρmin = −0.29 e Å−3 |
324 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.05391 (18) | 1.17583 (19) | 0.56437 (14) | 0.0382 (8) | |
N12 | 0.13002 (14) | 0.97933 (17) | 0.66837 (13) | 0.0364 (7) | |
C2 | 0.0227 (2) | 1.2729 (2) | 0.51338 (17) | 0.0498 (10) | |
C3 | −0.0746 (2) | 1.2890 (3) | 0.47489 (18) | 0.0574 (10) | |
C4 | −0.1379 (2) | 1.2056 (3) | 0.49016 (18) | 0.0533 (11) | |
C5 | −0.10528 (18) | 1.1038 (2) | 0.54406 (16) | 0.0401 (9) | |
C6 | −0.16693 (19) | 1.0148 (3) | 0.56456 (18) | 0.0497 (10) | |
C7 | −0.13202 (18) | 0.9219 (3) | 0.61895 (18) | 0.0475 (10) | |
C8 | −0.03095 (17) | 0.9048 (2) | 0.65657 (15) | 0.0354 (8) | |
C9 | 0.0097 (2) | 0.8067 (2) | 0.71173 (17) | 0.0437 (9) | |
C10 | 0.1068 (2) | 0.7959 (2) | 0.74208 (18) | 0.0469 (10) | |
C11 | 0.16361 (19) | 0.8837 (2) | 0.71874 (16) | 0.0427 (9) | |
C13 | 0.03328 (16) | 0.9889 (2) | 0.63748 (14) | 0.0293 (7) | |
C14 | −0.00593 (17) | 1.0909 (2) | 0.58142 (14) | 0.0306 (8) | |
N15 | −0.07856 (15) | 0.34171 (18) | 0.92218 (13) | 0.0339 (7) | |
N26 | 0.08664 (14) | 0.25794 (18) | 1.03725 (13) | 0.0378 (7) | |
C16 | −0.15449 (18) | 0.3854 (2) | 0.86201 (17) | 0.0424 (9) | |
C17 | −0.24346 (18) | 0.3314 (3) | 0.84870 (17) | 0.0460 (9) | |
C18 | −0.25201 (17) | 0.2333 (2) | 0.89907 (17) | 0.0428 (9) | |
C19 | −0.17174 (16) | 0.1862 (2) | 0.96188 (15) | 0.0339 (8) | |
C20 | −0.17495 (18) | 0.0817 (2) | 1.01531 (17) | 0.0411 (9) | |
C21 | −0.09527 (18) | 0.0398 (2) | 1.07310 (16) | 0.0407 (9) | |
C22 | −0.00318 (17) | 0.0967 (2) | 1.08369 (15) | 0.0327 (8) | |
C23 | 0.08261 (19) | 0.0549 (2) | 1.14257 (16) | 0.0417 (9) | |
C24 | 0.16602 (19) | 0.1130 (2) | 1.14723 (17) | 0.0473 (9) | |
C25 | 0.16456 (18) | 0.2136 (3) | 1.09347 (18) | 0.0470 (9) | |
C27 | 0.00304 (16) | 0.1986 (2) | 1.03291 (15) | 0.0291 (7) | |
C28 | −0.08273 (16) | 0.2437 (2) | 0.97183 (15) | 0.0287 (7) | |
Zn1 | 0.02573 (2) | 0.43561 (2) | 0.73719 (2) | 0.0324 (1) | |
Cl1 | −0.11018 (5) | 0.52315 (6) | 0.64898 (5) | 0.0584 (3) | |
Cl2 | 0.15128 (4) | 0.45542 (6) | 0.68453 (4) | 0.0445 (2) | |
Cl3 | 0.06504 (5) | 0.53130 (5) | 0.86969 (4) | 0.0429 (2) | |
Cl4 | −0.00552 (5) | 0.23479 (5) | 0.76075 (4) | 0.0433 (2) | |
O1 | −0.25358 (17) | 0.2883 (3) | 0.61679 (19) | 0.0609 (9) | |
H1 | 0.1064 (18) | 1.169 (2) | 0.5852 (17) | 0.033 (8)* | |
H2 | 0.06620 | 1.32970 | 0.50370 | 0.0600* | |
H3 | −0.09690 | 1.35620 | 0.43880 | 0.0690* | |
H4 | −0.20340 | 1.21660 | 0.46450 | 0.0640* | |
H6 | −0.23290 | 1.02140 | 0.53950 | 0.0600* | |
H7 | −0.17430 | 0.86710 | 0.63270 | 0.0570* | |
H9 | −0.02950 | 0.74930 | 0.72740 | 0.0530* | |
H10 | 0.13470 | 0.73060 | 0.77800 | 0.0560* | |
H11 | 0.22980 | 0.87460 | 0.74000 | 0.0510* | |
H15 | −0.0270 (18) | 0.379 (2) | 0.9296 (16) | 0.040 (8)* | |
H16 | −0.14770 | 0.45270 | 0.82870 | 0.0510* | |
H17 | −0.29670 | 0.36120 | 0.80630 | 0.0550* | |
H18 | −0.31190 | 0.19750 | 0.89150 | 0.0510* | |
H20 | −0.23320 | 0.04250 | 1.00970 | 0.0490* | |
H21 | −0.09940 | −0.02770 | 1.10720 | 0.0490* | |
H23 | 0.08200 | −0.01220 | 1.17810 | 0.0500* | |
H24 | 0.22340 | 0.08620 | 1.18570 | 0.0570* | |
H25 | 0.22260 | 0.25230 | 1.09750 | 0.0560* | |
H1A | −0.217 (3) | 0.344 (3) | 0.620 (2) | 0.083 (15)* | |
H1B | −0.239 (3) | 0.241 (3) | 0.650 (2) | 0.079 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0427 (15) | 0.0374 (13) | 0.0337 (13) | 0.0058 (11) | 0.0103 (11) | 0.0005 (10) |
N12 | 0.0342 (11) | 0.0336 (11) | 0.0368 (12) | 0.0014 (9) | 0.0034 (9) | −0.0013 (9) |
C2 | 0.081 (2) | 0.0349 (15) | 0.0369 (17) | 0.0056 (14) | 0.0228 (15) | 0.0018 (12) |
C3 | 0.087 (2) | 0.0461 (17) | 0.0368 (17) | 0.0339 (17) | 0.0149 (16) | 0.0047 (13) |
C4 | 0.0546 (18) | 0.066 (2) | 0.0358 (17) | 0.0293 (16) | 0.0081 (14) | −0.0022 (14) |
C5 | 0.0395 (15) | 0.0489 (15) | 0.0312 (15) | 0.0145 (12) | 0.0096 (12) | −0.0083 (12) |
C6 | 0.0301 (14) | 0.0680 (19) | 0.0472 (18) | 0.0052 (14) | 0.0058 (13) | −0.0136 (15) |
C7 | 0.0374 (15) | 0.0549 (17) | 0.0524 (18) | −0.0112 (13) | 0.0168 (13) | −0.0128 (14) |
C8 | 0.0396 (14) | 0.0367 (13) | 0.0299 (14) | −0.0049 (11) | 0.0105 (11) | −0.0108 (11) |
C9 | 0.0582 (18) | 0.0342 (14) | 0.0405 (16) | −0.0133 (13) | 0.0173 (14) | −0.0057 (12) |
C10 | 0.0600 (19) | 0.0330 (14) | 0.0402 (16) | 0.0000 (13) | 0.0036 (14) | 0.0023 (12) |
C11 | 0.0407 (15) | 0.0394 (14) | 0.0388 (16) | 0.0024 (12) | −0.0019 (12) | −0.0012 (12) |
C13 | 0.0325 (13) | 0.0291 (12) | 0.0248 (13) | 0.0011 (10) | 0.0062 (10) | −0.0079 (10) |
C14 | 0.0365 (13) | 0.0317 (13) | 0.0241 (13) | 0.0034 (11) | 0.0099 (11) | −0.0065 (10) |
N15 | 0.0305 (12) | 0.0374 (12) | 0.0362 (13) | 0.0010 (10) | 0.0138 (10) | 0.0036 (10) |
N26 | 0.0319 (11) | 0.0453 (12) | 0.0355 (13) | −0.0040 (9) | 0.0090 (9) | 0.0053 (10) |
C16 | 0.0423 (15) | 0.0481 (15) | 0.0396 (16) | 0.0136 (13) | 0.0164 (12) | 0.0134 (12) |
C17 | 0.0326 (15) | 0.0642 (18) | 0.0382 (16) | 0.0129 (13) | 0.0059 (12) | 0.0039 (14) |
C18 | 0.0282 (13) | 0.0558 (17) | 0.0437 (17) | −0.0009 (12) | 0.0098 (12) | −0.0058 (13) |
C19 | 0.0320 (13) | 0.0379 (13) | 0.0340 (15) | −0.0021 (11) | 0.0131 (11) | −0.0053 (11) |
C20 | 0.0382 (15) | 0.0454 (15) | 0.0435 (16) | −0.0125 (12) | 0.0180 (13) | −0.0040 (13) |
C21 | 0.0482 (16) | 0.0377 (14) | 0.0404 (16) | −0.0082 (12) | 0.0195 (13) | 0.0033 (12) |
C22 | 0.0389 (14) | 0.0338 (13) | 0.0277 (13) | 0.0002 (11) | 0.0137 (11) | −0.0008 (11) |
C23 | 0.0520 (17) | 0.0420 (15) | 0.0316 (15) | 0.0045 (13) | 0.0133 (12) | 0.0067 (12) |
C24 | 0.0388 (15) | 0.0594 (17) | 0.0373 (16) | 0.0056 (13) | 0.0015 (12) | 0.0101 (14) |
C25 | 0.0305 (14) | 0.0625 (18) | 0.0444 (17) | −0.0057 (13) | 0.0057 (12) | 0.0052 (14) |
C27 | 0.0302 (12) | 0.0321 (13) | 0.0264 (13) | −0.0010 (10) | 0.0106 (10) | −0.0030 (10) |
C28 | 0.0336 (13) | 0.0285 (12) | 0.0267 (13) | −0.0002 (10) | 0.0132 (10) | −0.0025 (10) |
Zn1 | 0.0315 (2) | 0.0318 (2) | 0.0336 (2) | −0.0033 (1) | 0.0091 (1) | −0.0023 (1) |
Cl1 | 0.0373 (4) | 0.0486 (4) | 0.0735 (5) | −0.0010 (3) | −0.0074 (3) | 0.0052 (4) |
Cl2 | 0.0409 (4) | 0.0505 (4) | 0.0470 (4) | −0.0073 (3) | 0.0208 (3) | −0.0059 (3) |
Cl3 | 0.0575 (4) | 0.0369 (3) | 0.0369 (4) | −0.0085 (3) | 0.0182 (3) | −0.0086 (3) |
Cl4 | 0.0575 (4) | 0.0299 (3) | 0.0460 (4) | −0.0072 (3) | 0.0210 (3) | −0.0050 (3) |
O1 | 0.0530 (14) | 0.0493 (14) | 0.083 (2) | 0.0033 (13) | 0.0242 (13) | 0.0021 (14) |
Zn1—Cl4 | 2.2728 (6) | C2—H2 | 0.9300 |
Zn1—Cl1 | 2.2798 (8) | C3—H3 | 0.9300 |
Zn1—Cl2 | 2.2556 (7) | C4—H4 | 0.9300 |
Zn1—Cl3 | 2.3085 (7) | C6—H6 | 0.9300 |
O1—H1A | 0.80 (4) | C7—H7 | 0.9300 |
O1—H1B | 0.73 (3) | C9—H9 | 0.9300 |
N1—C2 | 1.331 (3) | C10—H10 | 0.9300 |
N1—C14 | 1.352 (3) | C11—H11 | 0.9300 |
N12—C13 | 1.355 (3) | C16—C17 | 1.381 (4) |
N12—C11 | 1.320 (3) | C17—C18 | 1.369 (4) |
N1—H1 | 0.74 (3) | C18—C19 | 1.402 (3) |
N15—C28 | 1.345 (3) | C19—C20 | 1.435 (3) |
N15—C16 | 1.329 (3) | C19—C28 | 1.406 (3) |
N26—C25 | 1.320 (4) | C20—C21 | 1.339 (4) |
N26—C27 | 1.362 (3) | C21—C22 | 1.441 (4) |
N15—H15 | 0.83 (3) | C22—C27 | 1.397 (3) |
C2—C3 | 1.382 (4) | C22—C23 | 1.406 (4) |
C3—C4 | 1.366 (4) | C23—C24 | 1.352 (4) |
C4—C5 | 1.400 (4) | C24—C25 | 1.393 (4) |
C5—C6 | 1.424 (4) | C27—C28 | 1.433 (3) |
C5—C14 | 1.403 (4) | C16—H16 | 0.9300 |
C6—C7 | 1.336 (4) | C17—H17 | 0.9300 |
C7—C8 | 1.431 (4) | C18—H18 | 0.9300 |
C8—C13 | 1.406 (3) | C20—H20 | 0.9300 |
C8—C9 | 1.402 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.360 (4) | C23—H23 | 0.9300 |
C10—C11 | 1.386 (4) | C24—H24 | 0.9300 |
C13—C14 | 1.437 (3) | C25—H25 | 0.9300 |
Cl3—Zn1—Cl4 | 105.98 (2) | C8—C7—H7 | 119.00 |
Cl1—Zn1—Cl4 | 108.76 (3) | C8—C9—H9 | 120.00 |
Cl1—Zn1—Cl2 | 111.95 (3) | C10—C9—H9 | 120.00 |
Cl1—Zn1—Cl3 | 109.35 (3) | C9—C10—H10 | 120.00 |
Cl2—Zn1—Cl3 | 108.14 (3) | C11—C10—H10 | 120.00 |
Cl2—Zn1—Cl4 | 112.47 (3) | N12—C11—H11 | 118.00 |
H1A—O1—H1B | 116 (4) | C10—C11—H11 | 118.00 |
C2—N1—C14 | 122.8 (3) | N15—C16—C17 | 120.3 (2) |
C11—N12—C13 | 116.3 (2) | C16—C17—C18 | 118.9 (2) |
C14—N1—H1 | 118.7 (18) | C17—C18—C19 | 120.9 (2) |
C2—N1—H1 | 118.5 (18) | C18—C19—C28 | 117.8 (2) |
C16—N15—C28 | 123.1 (2) | C18—C19—C20 | 123.9 (2) |
C25—N26—C27 | 116.0 (2) | C20—C19—C28 | 118.3 (2) |
C28—N15—H15 | 119.8 (16) | C19—C20—C21 | 121.0 (2) |
C16—N15—H15 | 117.1 (16) | C20—C21—C22 | 121.6 (2) |
N1—C2—C3 | 119.8 (3) | C21—C22—C27 | 119.3 (2) |
C2—C3—C4 | 119.6 (3) | C23—C22—C27 | 117.1 (2) |
C3—C4—C5 | 120.7 (3) | C21—C22—C23 | 123.6 (2) |
C4—C5—C14 | 117.7 (2) | C22—C23—C24 | 119.6 (2) |
C4—C5—C6 | 123.9 (3) | C23—C24—C25 | 118.9 (2) |
C6—C5—C14 | 118.4 (2) | N26—C25—C24 | 124.7 (3) |
C5—C6—C7 | 121.4 (3) | C22—C27—C28 | 118.8 (2) |
C6—C7—C8 | 121.5 (3) | N26—C27—C28 | 117.4 (2) |
C9—C8—C13 | 116.6 (2) | N26—C27—C22 | 123.8 (2) |
C7—C8—C13 | 119.5 (2) | C19—C28—C27 | 121.1 (2) |
C7—C8—C9 | 123.9 (2) | N15—C28—C19 | 119.0 (2) |
C8—C9—C10 | 119.6 (2) | N15—C28—C27 | 119.9 (2) |
C9—C10—C11 | 119.1 (2) | N15—C16—H16 | 120.00 |
N12—C11—C10 | 124.4 (3) | C17—C16—H16 | 120.00 |
C8—C13—C14 | 118.1 (2) | C18—C17—H17 | 121.00 |
N12—C13—C14 | 117.9 (2) | C16—C17—H17 | 121.00 |
N12—C13—C8 | 124.0 (2) | C17—C18—H18 | 120.00 |
N1—C14—C5 | 119.4 (2) | C19—C18—H18 | 120.00 |
N1—C14—C13 | 119.5 (2) | C21—C20—H20 | 120.00 |
C5—C14—C13 | 121.1 (2) | C19—C20—H20 | 120.00 |
N1—C2—H2 | 120.00 | C20—C21—H21 | 119.00 |
C3—C2—H2 | 120.00 | C22—C21—H21 | 119.00 |
C4—C3—H3 | 120.00 | C22—C23—H23 | 120.00 |
C2—C3—H3 | 120.00 | C24—C23—H23 | 120.00 |
C3—C4—H4 | 120.00 | C23—C24—H24 | 121.00 |
C5—C4—H4 | 120.00 | C25—C24—H24 | 121.00 |
C5—C6—H6 | 119.00 | N26—C25—H25 | 118.00 |
C7—C6—H6 | 119.00 | C24—C25—H25 | 118.00 |
C6—C7—H7 | 119.00 | ||
C14—N1—C2—C3 | −0.6 (4) | C8—C9—C10—C11 | 1.0 (4) |
C2—N1—C14—C13 | −179.7 (2) | C9—C10—C11—N12 | 0.2 (4) |
C2—N1—C14—C5 | 0.3 (4) | C8—C13—C14—C5 | −2.4 (3) |
C11—N12—C13—C14 | −179.1 (2) | N12—C13—C14—C5 | 177.2 (2) |
C11—N12—C13—C8 | 0.5 (3) | C8—C13—C14—N1 | 177.6 (2) |
C13—N12—C11—C10 | −0.9 (4) | N12—C13—C14—N1 | −2.7 (3) |
C16—N15—C28—C27 | 177.3 (2) | N15—C16—C17—C18 | 0.7 (4) |
C28—N15—C16—C17 | 1.0 (4) | C16—C17—C18—C19 | −1.4 (4) |
C16—N15—C28—C19 | −1.9 (3) | C17—C18—C19—C28 | 0.6 (4) |
C25—N26—C27—C28 | −179.4 (2) | C17—C18—C19—C20 | −178.3 (2) |
C25—N26—C27—C22 | 0.0 (3) | C20—C19—C28—C27 | 0.8 (3) |
C27—N26—C25—C24 | −0.3 (4) | C18—C19—C20—C21 | 178.7 (2) |
N1—C2—C3—C4 | 0.6 (4) | C28—C19—C20—C21 | −0.1 (4) |
C2—C3—C4—C5 | −0.3 (4) | C18—C19—C28—C27 | −178.2 (2) |
C3—C4—C5—C14 | 0.0 (4) | C20—C19—C28—N15 | 180.0 (2) |
C3—C4—C5—C6 | 178.5 (3) | C18—C19—C28—N15 | 1.1 (3) |
C4—C5—C14—N1 | 0.0 (4) | C19—C20—C21—C22 | −0.5 (4) |
C4—C5—C6—C7 | −177.5 (3) | C20—C21—C22—C23 | −179.0 (2) |
C14—C5—C6—C7 | 1.0 (4) | C20—C21—C22—C27 | 0.5 (4) |
C4—C5—C14—C13 | −180.0 (2) | C23—C22—C27—N26 | 0.3 (3) |
C6—C5—C14—C13 | 1.5 (3) | C21—C22—C27—N26 | −179.2 (2) |
C6—C5—C14—N1 | −178.6 (2) | C21—C22—C27—C28 | 0.2 (3) |
C5—C6—C7—C8 | −2.4 (4) | C23—C22—C27—C28 | 179.7 (2) |
C6—C7—C8—C9 | −177.8 (3) | C21—C22—C23—C24 | 179.1 (2) |
C6—C7—C8—C13 | 1.4 (4) | C27—C22—C23—C24 | −0.5 (3) |
C7—C8—C9—C10 | 177.8 (3) | C22—C23—C24—C25 | 0.3 (4) |
C9—C8—C13—N12 | 0.6 (3) | C23—C24—C25—N26 | 0.2 (4) |
C7—C8—C13—N12 | −178.6 (2) | N26—C27—C28—N15 | −0.6 (3) |
C9—C8—C13—C14 | −179.7 (2) | C22—C27—C28—C19 | −0.8 (3) |
C7—C8—C13—C14 | 1.0 (3) | N26—C27—C28—C19 | 178.6 (2) |
C13—C8—C9—C10 | −1.4 (4) | C22—C27—C28—N15 | −180.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.74 (3) | 2.01 (3) | 2.711 (4) | 158 (2) |
O1—H1A···Cl1 | 0.80 (4) | 2.44 (4) | 3.231 (3) | 172 (3) |
O1—H1B···Cl2ii | 0.73 (3) | 2.82 (4) | 3.317 (3) | 128 (4) |
N15—H15···Cl3 | 0.83 (3) | 2.50 (2) | 3.225 (2) | 146 (2) |
C3—H3···Cl2iii | 0.93 | 2.80 | 3.728 (3) | 172 |
C24—H24···Cl2iv | 0.93 | 2.74 | 3.629 (3) | 160 |
N1—H1···N12 | 0.74 (3) | 2.42 (2) | 2.737 (3) | 107 (2) |
N15—H15···N26 | 0.83 (3) | 2.41 (2) | 2.731 (3) | 104 (2) |
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+1/2, z; (iii) −x, −y+2, −z+1; (iv) −x+1/2, y−1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.74 (3) | 2.01 (3) | 2.711 (4) | 158 (2) |
O1—H1A···Cl1 | 0.80 (4) | 2.44 (4) | 3.231 (3) | 172 (3) |
O1—H1B···Cl2ii | 0.73 (3) | 2.82 (4) | 3.317 (3) | 128 (4) |
N15—H15···Cl3 | 0.83 (3) | 2.50 (2) | 3.225 (2) | 146 (2) |
C3—H3···Cl2iii | 0.93 | 2.80 | 3.728 (3) | 172 |
C24—H24···Cl2iv | 0.93 | 2.74 | 3.629 (3) | 160 |
N1—H1···N12 | 0.74 (3) | 2.42 (2) | 2.737 (3) | 107 (2) |
N15—H15···N26 | 0.83 (3) | 2.41 (2) | 2.731 (3) | 104 (2) |
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+1/2, z; (iii) −x, −y+2, −z+1; (iv) −x+1/2, y−1/2, −z+2. |
Acknowledgements
EG and KA thank the CSIR, New Delhi (Lr: No. 01 (2570)/12/EMR-II/3.4.2012) for financial support through a major research project. The authors also thank the Department of Chemistry, Pondicherry University, for the single-crystal XRD instrumentation facility.
References
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As part of an ongoing investigation of the structures of and non-covalent interactions present in self-assembling organic and inorganic hybrid materials prepared by the combination of an organic cation and the tetrachloridozincate anion we synthesized the title compound. There are only a small number of structures of materials containing bis(1,10-phenanthrolinium) cations and perhalometallate anions in the Cambridge Structural Database (CSD; V5.35, last update Nov. 2013; Allen, 2002), and none of them involve the tetrachloridozincate anion.
The molecule structure of the title compound is shown in Fig. 1. The asymmetric unit contains one inorganic tetrachloridozincate anion and two 1,10-phenanthrolinium organic cations. The compound crystallized as a monohydrate. The tetrachlorozincate anion has a perfect tetrahedral coordination environment. The bond lengths Zn—Cl [2.556 (7) - 2.3085 (7) Å] and C—N [1.320 (3) - 1.362 (3) Å] are comparable with the values reported for Bis(10-methoxybenzo[h]quinolinium) tetrachloridozinc [Dong & Liu, 2012]. The sum of the bond angles around atoms N1 and N15 (360°) in the 1,10-phenanthrolinium cations indicates sp2 hybridization states. The two 1,10-phenanthrolinium ring systems (N1/N12/C2-C11/C13/C14) and (N15/N26/C16-C25/C27/C28) are planar with r.m.s values of 0.029 (3) and 0.022 (2) Å, respectively. In each 1,10-phenanthrolinium cation there is a short N-H···N interaction (Table 1).
In the crystal, the two independent 1,10-phenanthrolinium cations are bridged by the water molecule and the tetrachloridozinc anion via N-H···O, O-H···Cl and N-H···Cl hydrogen bonds (Table 1 and Fig. 2) forming chains along [100]. The chains are linked via C-H···Cl hydrogen bonds (Table 1) and a number of π-π interactions forming a three-dimensional network.
The centroid-centroid distances are 3.5594 (14) Å for Cg1···Cg2i [Cg1 and Cg2 and the centroids of rings N1/C2-C5/C14 and N12/C8-C11/C13, respectively; symmetry code: (i) = -x, -y+2, -z+1 ], 3.6501 (15) Å for Cg1···Cg3i [Cg3 is the centroid of ring C5-C8/C13/C14] and 3.7057 (13) Å for Cg8···Cg9ii [Cg8 and Cg9 are the centroids of rings N26/C22-C25/C27 and C19-C22/C27/C28, respectively; symmetry code: (ii) -x, -y, -z+2].