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In the title compound, [Zn(1,3-BDC)(L)]n, where 1,3-BDC is the 1,3-benzene­dicarboxyl­ate dianion (C8H4O42−) and L is 2-phenyl-1H-1,3,7,8,-tetra­azacyclo­penta­[l]phenanthrene (C19H12N4), each ZnII atom is five-coordinated by two N atoms from one L ligand, and three O atoms from three 1,3-BDC anions, in a distorted square-based pyramidal geometry. The ZnII atoms are bridged by the 1,3-BDC ligands to form a double-chain structure. N—H...O hydrogen bonds complete the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038098/hb2152sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038098/hb2152Isup2.hkl
Contains datablock I

CCDC reference: 624710

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.041
  • wR factor = 0.090
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

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.

Poly[[(2-phenyl-1H-1,3,7,8,-tetraazacyclopenta[l]phenanthrene)zinc(II)]- µ3-1,3-benzenedicarboxylato] top
Crystal data top
[Zn(C8H4O4)(C19H12N4)]F(000) = 2144
Mr = 525.81Dx = 1.576 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 13666 reflections
a = 16.846 (3) Åθ = 0.3–27.5°
b = 15.932 (3) ŵ = 1.15 mm1
c = 17.398 (4) ÅT = 292 K
β = 108.38 (3)°Block, yellow
V = 4431.3 (17) Å30.33 × 0.31 × 0.29 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5026 independent reflections
Radiation source: rotating anode3482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.4°
ω scansh = 2121
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2020
Tmin = 0.691, Tmax = 0.719l = 2222
20760 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0327P)2 + 4.2485P]
where P = (Fo2 + 2Fc2)/3
5026 reflections(Δ/σ)max = 0.001
325 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.40 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
C10.18393 (17)0.10347 (16)0.60230 (16)0.0293 (6)
C20.20464 (15)0.07493 (16)0.52837 (15)0.0265 (6)
C30.27882 (17)0.10059 (18)0.51666 (17)0.0375 (7)
H3A0.31660.13360.55540.045*
C40.29625 (18)0.0768 (2)0.44734 (19)0.0433 (7)
H40.34580.09440.43940.052*
C50.24092 (17)0.02733 (17)0.38957 (17)0.0348 (6)
H50.25310.01180.34300.042*
C60.16713 (16)0.00081 (15)0.40131 (15)0.0264 (6)
C70.14941 (16)0.02538 (15)0.47046 (14)0.0261 (6)
H70.09960.00830.47810.031*
C80.10589 (17)0.05247 (16)0.33863 (15)0.0297 (6)
C90.20489 (19)0.24880 (18)0.80253 (18)0.0424 (7)
H90.22860.19700.82150.051*
C100.2463 (2)0.32118 (19)0.83757 (19)0.0484 (8)
H100.29680.31750.87930.058*
C110.21294 (19)0.39779 (18)0.81091 (18)0.0417 (7)
H110.24000.44660.83470.050*
C120.13729 (17)0.40218 (17)0.74718 (16)0.0312 (6)
C130.09911 (16)0.32561 (16)0.71443 (16)0.0276 (6)
C140.02148 (17)0.32513 (17)0.64740 (16)0.0301 (6)
C150.08199 (19)0.2452 (2)0.56149 (19)0.0460 (8)
H150.10490.19280.54370.055*
C160.1241 (2)0.3164 (2)0.5231 (2)0.0531 (9)
H160.17410.31140.48080.064*
C170.0914 (2)0.3936 (2)0.5481 (2)0.0512 (9)
H170.11840.44170.52260.061*
C180.01664 (17)0.39986 (17)0.61251 (17)0.0337 (6)
C190.02313 (17)0.47690 (17)0.64560 (18)0.0349 (7)
C200.09587 (17)0.47701 (16)0.71043 (17)0.0319 (6)
C210.05446 (18)0.60551 (17)0.67241 (18)0.0366 (7)
C220.05414 (18)0.69748 (17)0.67039 (18)0.0376 (7)
C230.0983 (2)0.74469 (19)0.7372 (2)0.0459 (8)
H230.12990.71800.78450.055*
C240.0952 (2)0.8313 (2)0.7334 (2)0.0567 (10)
H240.12370.86280.77880.068*
C250.0503 (2)0.8712 (2)0.6629 (2)0.0592 (10)
H250.04960.92950.66020.071*
C260.0066 (2)0.8250 (2)0.5968 (2)0.0566 (9)
H260.02390.85190.54920.068*
C270.0079 (2)0.73833 (19)0.60048 (19)0.0468 (8)
H270.02270.70730.55560.056*
N10.01129 (14)0.24840 (14)0.62177 (14)0.0329 (5)
N20.13244 (14)0.25063 (13)0.74276 (13)0.0319 (5)
N30.11511 (15)0.55999 (13)0.72731 (14)0.0350 (5)
H30.15720.57960.76510.042*
N40.00190 (15)0.55771 (14)0.62161 (15)0.0402 (6)
O10.10636 (12)0.10485 (12)0.59466 (11)0.0363 (5)
O20.24013 (12)0.12282 (13)0.66459 (11)0.0436 (5)
O30.04130 (13)0.07486 (12)0.35351 (12)0.0422 (5)
O40.12472 (13)0.06948 (12)0.27606 (12)0.0404 (5)
Zn10.06563 (2)0.143258 (18)0.681927 (18)0.02816 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0312 (15)0.0257 (14)0.0272 (14)0.0035 (11)0.0036 (13)0.0007 (11)
C20.0255 (14)0.0259 (13)0.0244 (13)0.0028 (11)0.0026 (11)0.0001 (10)
C30.0282 (15)0.0422 (17)0.0364 (17)0.0090 (13)0.0022 (13)0.0072 (13)
C40.0302 (16)0.056 (2)0.0472 (19)0.0081 (14)0.0174 (15)0.0058 (15)
C50.0336 (15)0.0415 (17)0.0322 (16)0.0005 (13)0.0145 (13)0.0026 (12)
C60.0279 (14)0.0209 (12)0.0281 (14)0.0016 (11)0.0054 (11)0.0007 (10)
C70.0250 (13)0.0283 (14)0.0242 (13)0.0001 (11)0.0067 (11)0.0009 (10)
C80.0368 (16)0.0218 (13)0.0264 (14)0.0022 (12)0.0038 (12)0.0028 (11)
C90.0449 (18)0.0302 (16)0.0429 (18)0.0001 (14)0.0007 (15)0.0059 (13)
C100.0494 (19)0.0363 (17)0.0433 (19)0.0009 (15)0.0085 (16)0.0048 (14)
C110.0461 (18)0.0297 (16)0.0394 (18)0.0060 (13)0.0005 (15)0.0001 (12)
C120.0337 (15)0.0297 (15)0.0292 (15)0.0007 (12)0.0085 (13)0.0001 (11)
C130.0296 (14)0.0262 (14)0.0297 (14)0.0014 (11)0.0131 (12)0.0005 (11)
C140.0283 (14)0.0301 (14)0.0325 (15)0.0033 (12)0.0103 (13)0.0021 (11)
C150.0422 (18)0.0367 (18)0.051 (2)0.0076 (14)0.0026 (16)0.0022 (14)
C160.0396 (18)0.0451 (19)0.057 (2)0.0039 (15)0.0109 (17)0.0057 (16)
C170.0410 (19)0.0409 (18)0.059 (2)0.0040 (15)0.0032 (17)0.0025 (16)
C180.0280 (15)0.0323 (16)0.0382 (17)0.0006 (12)0.0066 (13)0.0021 (12)
C190.0333 (16)0.0286 (15)0.0409 (17)0.0004 (12)0.0089 (14)0.0011 (12)
C200.0338 (16)0.0255 (15)0.0352 (16)0.0006 (12)0.0091 (13)0.0007 (11)
C210.0354 (16)0.0307 (15)0.0403 (17)0.0038 (13)0.0069 (14)0.0001 (13)
C220.0376 (17)0.0278 (14)0.0428 (18)0.0043 (13)0.0060 (14)0.0049 (12)
C230.0450 (19)0.0360 (17)0.0483 (19)0.0065 (14)0.0028 (15)0.0029 (14)
C240.056 (2)0.0348 (18)0.068 (2)0.0012 (16)0.0039 (19)0.0137 (16)
C250.064 (2)0.0265 (17)0.080 (3)0.0091 (16)0.013 (2)0.0006 (16)
C260.062 (2)0.0368 (18)0.061 (2)0.0147 (17)0.0051 (19)0.0067 (16)
C270.0464 (19)0.0372 (17)0.0461 (19)0.0075 (14)0.0007 (16)0.0026 (14)
N10.0316 (13)0.0299 (13)0.0343 (13)0.0044 (10)0.0061 (11)0.0007 (10)
N20.0378 (13)0.0260 (12)0.0296 (13)0.0007 (10)0.0072 (11)0.0021 (9)
N30.0374 (13)0.0259 (12)0.0352 (13)0.0015 (10)0.0023 (11)0.0030 (10)
N40.0337 (14)0.0329 (14)0.0451 (15)0.0018 (11)0.0002 (12)0.0010 (11)
O10.0307 (11)0.0522 (12)0.0252 (10)0.0011 (9)0.0079 (9)0.0047 (8)
O20.0368 (11)0.0550 (13)0.0306 (11)0.0017 (10)0.0013 (10)0.0134 (9)
O30.0428 (12)0.0434 (12)0.0374 (12)0.0180 (10)0.0083 (10)0.0019 (9)
O40.0448 (12)0.0426 (12)0.0326 (11)0.0033 (10)0.0105 (10)0.0132 (9)
Zn10.03444 (18)0.02656 (16)0.02283 (16)0.00407 (15)0.00810 (13)0.00010 (13)
Geometric parameters (Å, º) top
C1—O21.232 (3)C15—C161.393 (4)
C1—O11.271 (3)C15—H150.9300
C1—C21.505 (4)C16—C171.361 (4)
C2—C71.383 (3)C16—H160.9300
C2—C31.389 (4)C17—C181.400 (4)
C3—C41.381 (4)C17—H170.9300
C3—H3A0.9300C18—C191.430 (4)
C4—C51.382 (4)C19—N41.378 (3)
C4—H40.9300C19—C201.379 (4)
C5—C61.388 (4)C20—N31.371 (3)
C5—H50.9300C21—N41.317 (4)
C6—C71.384 (3)C21—N31.366 (3)
C6—C81.505 (4)C21—C221.466 (4)
C7—H70.9300C22—C271.383 (4)
C8—O31.247 (3)C22—C231.387 (4)
C8—O41.256 (3)C23—C241.381 (4)
C9—N21.331 (4)C23—H230.9300
C9—C101.386 (4)C24—C251.378 (5)
C9—H90.9300C24—H240.9300
C10—C111.362 (4)C25—C261.368 (5)
C10—H100.9300C25—H250.9300
C11—C121.403 (4)C26—C271.382 (4)
C11—H110.9300C26—H260.9300
C12—C131.413 (4)C27—H270.9300
C12—C201.427 (4)Zn1—N12.174 (2)
C13—N21.346 (3)Zn1—N22.136 (2)
C13—C141.452 (4)Zn1—O11.9513 (18)
C14—N11.358 (3)Zn1—O3i2.0277 (19)
C14—C181.397 (4)Zn1—O4ii2.0067 (19)
C15—N11.316 (4)N3—H30.8600
O2—C1—O1124.5 (3)C14—C18—C19117.6 (2)
O2—C1—C2120.4 (2)C17—C18—C19124.9 (3)
O1—C1—C2115.1 (2)N4—C19—C20110.8 (2)
C7—C2—C3119.4 (2)N4—C19—C18128.3 (3)
C7—C2—C1120.7 (2)C20—C19—C18120.9 (3)
C3—C2—C1119.9 (2)N3—C20—C19105.4 (2)
C4—C3—C2119.7 (3)N3—C20—C12131.3 (3)
C4—C3—H3A120.1C19—C20—C12123.2 (3)
C2—C3—H3A120.1N4—C21—N3112.6 (2)
C3—C4—C5120.7 (3)N4—C21—C22124.5 (3)
C3—C4—H4119.6N3—C21—C22122.9 (3)
C5—C4—H4119.6C27—C22—C23119.1 (3)
C4—C5—C6119.8 (3)C27—C22—C21119.2 (3)
C4—C5—H5120.1C23—C22—C21121.7 (3)
C6—C5—H5120.1C24—C23—C22120.0 (3)
C7—C6—C5119.4 (2)C24—C23—H23120.0
C7—C6—C8120.2 (2)C22—C23—H23120.0
C5—C6—C8120.4 (2)C25—C24—C23120.3 (3)
C2—C7—C6121.0 (2)C25—C24—H24119.8
C2—C7—H7119.5C23—C24—H24119.8
C6—C7—H7119.5C26—C25—C24119.9 (3)
O3—C8—O4126.4 (3)C26—C25—H25120.0
O3—C8—C6117.0 (2)C24—C25—H25120.0
O4—C8—C6116.6 (2)C25—C26—C27120.2 (3)
N2—C9—C10122.4 (3)C25—C26—H26119.9
N2—C9—H9118.8C27—C26—H26119.9
C10—C9—H9118.8C26—C27—C22120.5 (3)
C11—C10—C9120.0 (3)C26—C27—H27119.8
C11—C10—H10120.0C22—C27—H27119.8
C9—C10—H10120.0C15—N1—C14118.0 (2)
C10—C11—C12119.2 (3)C15—N1—Zn1127.3 (2)
C10—C11—H11120.4C14—N1—Zn1114.63 (18)
C12—C11—H11120.4C9—N2—C13118.7 (2)
C11—C12—C13117.4 (2)C9—N2—Zn1125.44 (19)
C11—C12—C20126.2 (3)C13—N2—Zn1115.83 (17)
C13—C12—C20116.4 (2)C21—N3—C20106.7 (2)
N2—C13—C12122.3 (2)C21—N3—H3126.6
N2—C13—C14117.1 (2)C20—N3—H3126.6
C12—C13—C14120.6 (2)C21—N4—C19104.5 (2)
N1—C14—C18122.7 (2)C1—O1—Zn1121.75 (17)
N1—C14—C13116.0 (2)C8—O3—Zn1i147.14 (19)
C18—C14—C13121.2 (2)C8—O4—Zn1iii129.65 (19)
N1—C15—C16123.1 (3)O1—Zn1—O4ii104.22 (8)
N1—C15—H15118.4O1—Zn1—O3i95.25 (8)
C16—C15—H15118.4O4ii—Zn1—O3i95.62 (9)
C17—C16—C15119.3 (3)O1—Zn1—N2112.15 (9)
C17—C16—H16120.4O4ii—Zn1—N290.94 (9)
C15—C16—H16120.4O3i—Zn1—N2149.30 (9)
C16—C17—C18119.5 (3)O1—Zn1—N199.76 (9)
C16—C17—H17120.3O4ii—Zn1—N1155.69 (9)
C18—C17—H17120.3O3i—Zn1—N186.00 (9)
C14—C18—C17117.4 (3)N2—Zn1—N176.25 (8)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z+1/2; (iii) x, y, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O2iv0.861.902.756 (3)170
Symmetry code: (iv) x+1/2, y+1/2, z+3/2.
 

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