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In the compound μ2-1,4-benzene­dicarboxyl­ate-κ2O,O′-bis{aqua­chloro[4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)phenol-κ2N,N′]zinc(II)} dihydrate, [Zn2Cl2(1,4-BDC)(L)2(H2O)2]·2H2O, where 1,4-BDC is the 1,4-benzene­dicarboxyl­ate dianion, C8H4O42−, and L is 4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)phenol, C19H12N4O, the ZnII atom is five-coordinated by two N atoms from one L ligand, one Cl ion, an O atom from a 1,4-BDC anion and one water mol­ecule in an approximate trigonal–bipyramidal geometry. The complete 1,4-BDC ligand is generated by inversion symmetry; it bridges two ZnII atoms to form a dinuclear complex. Neighbouring complexes inter­act through π–π contacts and various kinds of hydrogen bonds, leading to a two-dimensional supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021246/hb2075sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021246/hb2075Isup2.hkl
Contains datablock I

CCDC reference: 613695

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.113
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O2W - HW22 ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported HW22 .. CL1 .. 2.85 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

µ2-1,4-benzenedicarboxylate-κ2O,O'[bis[aquachloro-4-(1H-1,3,7,8- tetraazacyclopenta[l]phenanthren-2-yl)phenol-κ2N,N']zinc(II)] dihydrate top
Crystal data top
[Zn2Cl2(C8H4O4)(C19H12N4O)2(H2O)2]·2H2OZ = 1
Mr = 1062.47F(000) = 542
Triclinic, P1Dx = 1.672 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1608 (18) ÅCell parameters from 7257 reflections
b = 9.4769 (19) Åθ = 3.3–27.5°
c = 13.334 (3) ŵ = 1.34 mm1
α = 109.24 (3)°T = 292 K
β = 90.66 (3)°Block, yellow
γ = 104.02 (3)°0.29 × 0.25 × 0.21 mm
V = 1055.1 (5) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4780 independent reflections
Radiation source: rotating anode3065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.3°
ω scansh = 1111
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1212
Tmin = 0.684, Tmax = 0.758l = 1717
10429 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0392P)2 + 0.7847P]
where P = (Fo2 + 2Fc2)/3
4780 reflections(Δ/σ)max = 0.001
321 parametersΔρmax = 0.74 e Å3
3 restraintsΔρmin = 0.43 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9669 (4)0.7960 (5)0.3295 (3)0.0395 (10)
H11.04570.76490.35310.047*
C21.0013 (5)0.9286 (5)0.3025 (3)0.0415 (11)
H21.10140.98480.30820.050*
C30.8875 (4)0.9768 (5)0.2673 (3)0.0362 (10)
H30.90901.06640.24980.043*
C40.7374 (4)0.8882 (4)0.2580 (3)0.0255 (8)
C50.7119 (4)0.7549 (4)0.2870 (3)0.0268 (8)
C60.5606 (4)0.6583 (4)0.2806 (3)0.0244 (8)
C70.4110 (4)0.4480 (5)0.3136 (3)0.0319 (9)
H70.40220.36580.33850.038*
C80.2801 (5)0.4724 (5)0.2760 (3)0.0344 (9)
H80.18610.40730.27600.041*
C90.2908 (4)0.5925 (5)0.2393 (3)0.0313 (9)
H90.20440.60900.21280.038*
C100.4336 (4)0.6909 (4)0.2418 (3)0.0254 (8)
C110.4622 (4)0.8246 (4)0.2106 (3)0.0257 (8)
C120.6065 (4)0.9177 (4)0.2205 (3)0.0280 (8)
C130.4428 (4)1.0063 (4)0.1535 (3)0.0303 (9)
C140.3841 (4)1.1032 (4)0.1065 (3)0.0289 (8)
C150.2298 (5)1.0816 (5)0.0882 (3)0.0366 (9)
H150.16351.00530.10700.044*
C160.1720 (5)1.1704 (5)0.0427 (3)0.0405 (10)
H160.06801.15470.03190.049*
C170.2694 (5)1.2830 (5)0.0132 (3)0.0356 (9)
C180.4241 (5)1.3061 (5)0.0307 (3)0.0356 (9)
H180.49021.38200.01140.043*
C190.4805 (5)1.2169 (5)0.0768 (3)0.0335 (9)
H190.58461.23320.08810.040*
C200.6948 (4)0.2648 (4)0.4631 (3)0.0298 (9)
C210.5926 (4)0.1264 (4)0.4807 (3)0.0265 (8)
C220.4369 (4)0.0984 (4)0.4681 (3)0.0307 (9)
H220.39400.16450.44650.037*
C230.3454 (4)0.0261 (5)0.4872 (3)0.0318 (9)
H230.24090.04350.47870.038*
N10.8264 (3)0.7114 (4)0.3231 (2)0.0296 (7)
N20.5478 (3)0.5374 (3)0.3154 (2)0.0271 (7)
N30.3606 (3)0.8805 (4)0.1686 (2)0.0299 (7)
N40.5907 (4)1.0336 (4)0.1846 (2)0.0298 (7)
H40.66221.11000.18240.036*
O10.6346 (3)0.3325 (3)0.4135 (2)0.0405 (7)
O20.8287 (3)0.3067 (3)0.5005 (2)0.0449 (8)
O1W0.8694 (4)0.6100 (4)0.5082 (2)0.0419 (8)
O30.2213 (4)1.3747 (3)0.0318 (2)0.0481 (8)
H3A0.12851.35140.03880.072*
O2W0.0842 (4)0.6786 (4)0.0430 (3)0.0604 (9)
Zn10.75014 (5)0.50066 (5)0.35762 (4)0.03021 (14)
Cl10.86655 (11)0.35345 (12)0.22822 (8)0.0415 (3)
HW110.961 (7)0.641 (7)0.503 (4)0.07 (2)*
HW120.860 (6)0.527 (6)0.524 (4)0.059 (16)*
HW210.169 (4)0.733 (6)0.084 (3)0.089*
HW220.121 (5)0.626 (6)0.020 (2)0.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.024 (2)0.040 (3)0.060 (3)0.0024 (19)0.0022 (18)0.029 (2)
C20.024 (2)0.041 (3)0.063 (3)0.0026 (19)0.0037 (18)0.031 (2)
C30.032 (2)0.033 (2)0.049 (2)0.0008 (19)0.0004 (17)0.0253 (19)
C40.027 (2)0.0231 (19)0.0273 (19)0.0043 (16)0.0021 (14)0.0114 (15)
C50.027 (2)0.023 (2)0.0280 (19)0.0037 (16)0.0006 (14)0.0076 (15)
C60.028 (2)0.0223 (19)0.0262 (18)0.0067 (16)0.0033 (14)0.0118 (14)
C70.034 (2)0.030 (2)0.037 (2)0.0073 (18)0.0054 (16)0.0191 (17)
C80.028 (2)0.032 (2)0.043 (2)0.0004 (18)0.0042 (16)0.0181 (18)
C90.026 (2)0.033 (2)0.036 (2)0.0060 (18)0.0039 (15)0.0144 (17)
C100.026 (2)0.026 (2)0.0255 (19)0.0069 (16)0.0051 (14)0.0108 (15)
C110.0229 (19)0.025 (2)0.0295 (19)0.0066 (16)0.0042 (14)0.0101 (15)
C120.031 (2)0.023 (2)0.031 (2)0.0065 (17)0.0009 (15)0.0117 (15)
C130.036 (2)0.024 (2)0.033 (2)0.0095 (18)0.0002 (16)0.0124 (16)
C140.033 (2)0.022 (2)0.032 (2)0.0070 (17)0.0029 (15)0.0110 (15)
C150.031 (2)0.033 (2)0.051 (2)0.0077 (19)0.0003 (17)0.0229 (19)
C160.040 (3)0.036 (2)0.050 (3)0.013 (2)0.0079 (19)0.019 (2)
C170.050 (3)0.028 (2)0.034 (2)0.0144 (19)0.0033 (17)0.0139 (17)
C180.041 (2)0.028 (2)0.042 (2)0.0085 (19)0.0038 (17)0.0179 (18)
C190.033 (2)0.033 (2)0.040 (2)0.0123 (18)0.0014 (16)0.0166 (18)
C200.029 (2)0.027 (2)0.034 (2)0.0001 (17)0.0022 (15)0.0164 (16)
C210.030 (2)0.0227 (19)0.0246 (18)0.0005 (16)0.0042 (14)0.0110 (15)
C220.029 (2)0.030 (2)0.041 (2)0.0070 (17)0.0016 (16)0.0216 (17)
C230.028 (2)0.033 (2)0.034 (2)0.0002 (18)0.0016 (15)0.0164 (17)
N10.0281 (18)0.0257 (18)0.0391 (18)0.0065 (14)0.0009 (13)0.0167 (14)
N20.0249 (17)0.0241 (17)0.0354 (17)0.0025 (14)0.0041 (12)0.0170 (14)
N30.0284 (18)0.0306 (18)0.0355 (17)0.0105 (15)0.0028 (13)0.0156 (14)
N40.0285 (18)0.0256 (18)0.0395 (18)0.0047 (14)0.0013 (13)0.0182 (14)
O10.0352 (17)0.0379 (17)0.0566 (18)0.0003 (13)0.0022 (13)0.0342 (15)
O20.0293 (17)0.0437 (19)0.0643 (19)0.0067 (14)0.0057 (13)0.0338 (15)
O1W0.036 (2)0.0391 (19)0.0515 (19)0.0017 (15)0.0010 (14)0.0250 (15)
O30.054 (2)0.0438 (19)0.0597 (19)0.0187 (16)0.0018 (15)0.0306 (15)
O2W0.047 (2)0.049 (2)0.075 (2)0.0107 (18)0.0118 (17)0.0103 (18)
Zn10.0266 (3)0.0266 (3)0.0424 (3)0.00442 (19)0.00095 (17)0.02003 (19)
Cl10.0323 (6)0.0324 (6)0.0596 (7)0.0079 (5)0.0084 (4)0.0159 (5)
Geometric parameters (Å, º) top
Zn1—O12.049 (3)C13—N31.325 (5)
Zn1—O1W2.080 (3)C13—N41.349 (5)
Zn1—N12.150 (3)C13—C141.462 (5)
Zn1—N22.072 (3)C14—C151.385 (5)
Zn1—Cl12.2885 (14)C14—C191.388 (5)
C1—N11.327 (5)C15—C161.379 (5)
C1—C21.385 (5)C15—H150.9300
C1—H10.9300C16—C171.382 (6)
C2—C31.370 (6)C16—H160.9300
C2—H20.9300C17—O31.354 (4)
C3—C41.407 (5)C17—C181.386 (6)
C3—H30.9300C18—C191.381 (5)
C4—C51.407 (5)C18—H180.9300
C4—C121.416 (5)C19—H190.9300
C5—N11.354 (5)C20—O21.237 (4)
C5—C61.448 (5)C20—O11.263 (4)
C6—N21.352 (4)C20—C211.505 (5)
C6—C101.407 (5)C21—C221.384 (5)
C7—N21.327 (5)C21—C23i1.390 (5)
C7—C81.392 (5)C22—C231.373 (5)
C7—H70.9300C22—H220.9300
C8—C91.363 (5)C23—C21i1.390 (5)
C8—H80.9300C23—H230.9300
C9—C101.403 (5)N4—H40.8600
C9—H90.9300O1W—HW110.83 (6)
C10—C111.427 (5)O1W—HW120.87 (5)
C11—N31.372 (4)O3—H3A0.8200
C11—C121.378 (5)O2W—HW210.88 (4)
C12—N41.370 (4)O2W—HW220.941 (19)
N1—C1—C2122.8 (4)O3—C17—C16123.1 (4)
N1—C1—H1118.6O3—C17—C18117.4 (4)
C2—C1—H1118.6C16—C17—C18119.5 (4)
C3—C2—C1119.8 (4)C19—C18—C17120.2 (4)
C3—C2—H2120.1C19—C18—H18119.9
C1—C2—H2120.1C17—C18—H18119.9
C2—C3—C4118.8 (4)C18—C19—C14120.9 (4)
C2—C3—H3120.6C18—C19—H19119.6
C4—C3—H3120.6C14—C19—H19119.6
C3—C4—C5117.9 (3)O2—C20—O1124.9 (3)
C3—C4—C12126.6 (3)O2—C20—C21118.4 (3)
C5—C4—C12115.5 (3)O1—C20—C21116.6 (3)
N1—C5—C4122.0 (3)C22—C21—C23i118.9 (3)
N1—C5—C6116.7 (3)C22—C21—C20121.2 (3)
C4—C5—C6121.3 (3)C23i—C21—C20119.8 (3)
N2—C6—C10122.0 (3)C23—C22—C21120.5 (4)
N2—C6—C5116.6 (3)C23—C22—H22119.8
C10—C6—C5121.4 (3)C21—C22—H22119.8
N2—C7—C8122.7 (4)C22—C23—C21i120.6 (4)
N2—C7—H7118.7C22—C23—H23119.7
C8—C7—H7118.7C21i—C23—H23119.7
C9—C8—C7119.5 (4)C1—N1—C5118.7 (3)
C9—C8—H8120.3C1—N1—Zn1128.5 (3)
C7—C8—H8120.3C5—N1—Zn1112.8 (2)
C8—C9—C10119.3 (4)C7—N2—C6118.7 (3)
C8—C9—H9120.4C7—N2—Zn1125.7 (3)
C10—C9—H9120.4C6—N2—Zn1115.5 (2)
C9—C10—C6117.8 (3)C13—N3—C11105.1 (3)
C9—C10—C11125.7 (3)C13—N4—C12107.8 (3)
C6—C10—C11116.4 (3)C13—N4—H4126.1
N3—C11—C12110.3 (3)C12—N4—H4126.1
N3—C11—C10128.4 (3)C20—O1—Zn1125.1 (2)
C12—C11—C10121.3 (3)Zn1—O1W—HW11110 (4)
N4—C12—C11105.1 (3)Zn1—O1W—HW1296 (3)
N4—C12—C4130.7 (3)HW11—O1W—HW12106 (5)
C11—C12—C4124.1 (3)C17—O3—H3A109.5
N3—C13—N4111.7 (3)HW21—O2W—HW22101 (3)
N3—C13—C14125.1 (3)O1—Zn1—N290.17 (11)
N4—C13—C14123.2 (3)O1—Zn1—O1W87.43 (13)
C15—C14—C19118.0 (3)N2—Zn1—O1W124.01 (13)
C15—C14—C13120.7 (3)O1—Zn1—N1163.57 (12)
C19—C14—C13121.2 (4)N2—Zn1—N178.13 (12)
C16—C15—C14121.6 (4)O1W—Zn1—N189.60 (13)
C16—C15—H15119.2O1—Zn1—Cl198.97 (10)
C14—C15—H15119.2N2—Zn1—Cl1118.99 (9)
C15—C16—C17119.7 (4)O1W—Zn1—Cl1116.62 (11)
C15—C16—H16120.1N1—Zn1—Cl196.81 (9)
C17—C16—H16120.1
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—HW12···O20.87 (5)1.95 (6)2.774 (5)158 (4)
O1W—HW11···O2ii0.83 (6)1.88 (6)2.700 (5)172 (6)
O3—H3A···O2Wiii0.821.902.713 (5)173
N4—H4···Cl1iv0.862.483.318 (4)165
O2W—HW21···N30.88 (4)2.01 (2)2.884 (5)172 (6)
O2W—HW22···Cl1v0.94 (2)2.85 (4)3.571 (4)134 (5)
Symmetry codes: (ii) x+2, y+1, z+1; (iii) x, y+2, z; (iv) x, y+1, z; (v) x+1, y+1, z.
 

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