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In the structure of the title complex, {[Cu2Cl2(C8H4O4)(C12H7N3O2)2]·2C3H7NO}n, each copper cation is surrounded by one O atom from a terephthalate (ta) ligand, two bridging Cl atoms, and two N atoms from a 5-nitro-1,10-phenanthroline ligand. Dimeric blocks of [Cu2(C12H7N3O2)2(ta)] are held together by two μ-chloro bridges, which create a one-dimensional architecture. There is a center of symmetry halfway between the two Cu atoms and the two Cl atoms and at the center of the phenyl ring of the ta group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021445/lh6116sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021445/lh6116Isup2.hkl
Contains datablock I

CCDC reference: 226637

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Some non-H atoms missing
  • R factor = 0.049
  • wR factor = 0.124
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
Alert level C CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.99 <> 1.01 Calculated formula weight = 934.6944 Formula weight given = 958.7000 CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 9 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.96 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O2 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N3 PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C17 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N4
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C36 H32 Cl2 Cu2 N8 O10 Atom count from _chemical_formula_moiety:C38 H32 Cl2 Cu2 N8 O10 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C36 H32 Cl2 Cu2 N8 O10 Atom count from the _atom_site data: C38 H32 Cl2 Cu2 N8 O10 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 1 From the CIF: _chemical_formula_sum C36 H32 Cl2 Cu2 N8 O10 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 36.00 38.00 -2.00 H 32.00 32.00 0.00 Cl 2.00 2.00 0.00 Cu 2.00 2.00 0.00 N 8.00 8.00 0.00 O 10.00 10.00 0.00
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

catena-Poly[[[di-µ-chloro-bis[(5-nitro-1,10-phenanthroline)copper(II)]]- µ-terephthalato] bis(N,N'-dimethylformamide)] top
Crystal data top
[Cu2Cl2(C8H4O4)(C12H7N3O2)2]·2C3H7NOZ = 1
Mr = 958.7F(000) = 488
Triclinic, P1Dx = 1.603 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4185 (11) ÅCell parameters from 2222 reflections
b = 10.2030 (12) Åθ = 4.8–53.3°
c = 12.3617 (15) ŵ = 1.27 mm1
α = 106.223 (2)°T = 293 K
β = 93.856 (2)°Needle, green
γ = 116.698 (2)°0.53 × 0.39 × 0.19 mm
V = 993.0 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4022 independent reflections
Radiation source: fine-focus sealed tube3093 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
φ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.504, Tmax = 0.786k = 1112
5614 measured reflectionsl = 1515
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0588P)2]
where P = (Fo2 + 2Fc2)/3
4022 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.72 e Å3
5 restraintsΔρmin = 0.39 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
Cu0.35716 (5)0.02614 (5)0.42589 (4)0.03572 (16)
Cl0.36022 (11)0.20081 (10)0.40832 (8)0.0441 (2)
O10.4602 (3)0.0541 (3)0.2983 (2)0.0460 (6)
O20.2117 (3)0.0962 (4)0.1874 (3)0.0657 (8)
O30.0841 (6)0.5735 (5)0.6293 (4)0.1127 (15)
O40.0465 (5)0.5253 (4)0.7813 (4)0.0969 (13)
O50.4639 (8)0.5256 (11)0.8090 (6)0.211 (4)
N10.3133 (3)0.2082 (3)0.4399 (3)0.0395 (7)
N20.2317 (3)0.0137 (3)0.5534 (2)0.0349 (6)
N30.0814 (4)0.5005 (4)0.6900 (4)0.0616 (10)
N40.6739 (9)0.5367 (9)0.9093 (5)0.1156 (18)
C10.3545 (5)0.3004 (5)0.3779 (4)0.0521 (10)
C20.3218 (5)0.4247 (5)0.3989 (4)0.0572 (11)
C30.2487 (5)0.4553 (5)0.4856 (4)0.0547 (10)
C40.2020 (4)0.3605 (4)0.5533 (3)0.0426 (8)
C50.1207 (4)0.3707 (4)0.6464 (3)0.0444 (9)
C60.0732 (4)0.2683 (4)0.7043 (3)0.0453 (9)
C70.1086 (4)0.1428 (4)0.6755 (3)0.0391 (8)
C80.0666 (5)0.0332 (5)0.7311 (4)0.0472 (9)
C90.1090 (5)0.0809 (5)0.6984 (4)0.0483 (9)
C100.1926 (4)0.0869 (4)0.6102 (3)0.0442 (9)
C110.1926 (4)0.1281 (4)0.5869 (3)0.0355 (7)
C120.2376 (4)0.2356 (4)0.5247 (3)0.0373 (8)
C130.3604 (5)0.0196 (5)0.2010 (4)0.0464 (9)
C140.4328 (4)0.0087 (4)0.0970 (3)0.0420 (8)
C150.5967 (5)0.0940 (5)0.1082 (4)0.0543 (10)
C160.3388 (5)0.1021 (5)0.0128 (4)0.0547 (10)
C170.5454 (15)0.470 (3)0.8513 (10)0.403 (18)
H170.49280.36150.83180.484*
C180.7610 (18)0.7020 (14)0.9382 (10)0.278 (8)
H18A0.86610.74370.98700.417*
H18B0.70100.74720.97830.417*
H18C0.77470.72650.86880.417*
C190.7571 (17)0.4681 (17)0.9510 (10)0.253 (7)
H19A0.67920.37140.95770.379*
H19B0.82740.53821.02540.379*
H19C0.82110.44820.89800.379*
H10.409 (4)0.275 (3)0.316 (3)0.025 (8)*
H20.365 (6)0.478 (6)0.351 (4)0.099 (18)*
H30.238 (5)0.542 (4)0.520 (4)0.078 (15)*
H40.026 (5)0.299 (5)0.776 (4)0.061 (12)*
H50.006 (4)0.041 (5)0.784 (3)0.064 (13)*
H60.067 (5)0.168 (4)0.719 (4)0.076 (14)*
H70.220 (4)0.175 (4)0.580 (3)0.051 (10)*
H80.669 (5)0.176 (5)0.185 (4)0.076 (14)*
H90.230 (3)0.165 (5)0.025 (4)0.098 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0431 (3)0.0419 (3)0.0379 (3)0.0264 (2)0.02044 (19)0.0237 (2)
Cl0.0537 (5)0.0390 (5)0.0498 (5)0.0278 (4)0.0185 (4)0.0193 (4)
O10.0541 (15)0.0625 (17)0.0374 (14)0.0320 (14)0.0257 (13)0.0302 (13)
O20.0502 (17)0.097 (2)0.0620 (19)0.0338 (17)0.0346 (15)0.0438 (17)
O30.184 (4)0.107 (3)0.129 (4)0.116 (3)0.079 (3)0.068 (3)
O40.130 (3)0.079 (2)0.107 (3)0.072 (2)0.065 (3)0.024 (2)
O50.106 (5)0.361 (11)0.132 (6)0.067 (6)0.028 (4)0.116 (6)
N10.0417 (16)0.0391 (16)0.0450 (17)0.0194 (14)0.0116 (14)0.0248 (14)
N20.0348 (15)0.0403 (16)0.0384 (16)0.0220 (13)0.0146 (13)0.0180 (13)
N30.062 (2)0.043 (2)0.079 (3)0.0291 (18)0.016 (2)0.015 (2)
N40.127 (5)0.157 (6)0.073 (4)0.075 (5)0.028 (3)0.043 (4)
C10.056 (2)0.053 (2)0.058 (3)0.028 (2)0.019 (2)0.030 (2)
C20.067 (3)0.054 (3)0.069 (3)0.031 (2)0.025 (2)0.042 (2)
C30.057 (3)0.043 (2)0.073 (3)0.027 (2)0.019 (2)0.027 (2)
C40.0384 (19)0.0330 (19)0.054 (2)0.0155 (16)0.0059 (17)0.0160 (17)
C50.039 (2)0.0331 (19)0.057 (2)0.0202 (17)0.0109 (18)0.0057 (17)
C60.041 (2)0.039 (2)0.050 (2)0.0170 (17)0.0141 (18)0.0092 (18)
C70.0325 (18)0.041 (2)0.042 (2)0.0179 (16)0.0092 (15)0.0123 (16)
C80.043 (2)0.057 (2)0.048 (2)0.0245 (19)0.0209 (18)0.0243 (19)
C90.051 (2)0.054 (2)0.053 (2)0.026 (2)0.0245 (19)0.035 (2)
C100.046 (2)0.052 (2)0.053 (2)0.0287 (19)0.0246 (18)0.0302 (19)
C110.0311 (17)0.0360 (18)0.0403 (19)0.0160 (15)0.0086 (15)0.0149 (16)
C120.0340 (18)0.0354 (18)0.041 (2)0.0169 (15)0.0072 (15)0.0120 (16)
C130.047 (2)0.057 (2)0.051 (2)0.030 (2)0.0255 (19)0.031 (2)
C140.041 (2)0.055 (2)0.039 (2)0.0240 (18)0.0187 (16)0.0268 (18)
C150.045 (2)0.063 (3)0.047 (2)0.015 (2)0.015 (2)0.026 (2)
C160.036 (2)0.070 (3)0.051 (3)0.014 (2)0.0177 (19)0.029 (2)
C170.121 (10)0.88 (5)0.088 (8)0.168 (17)0.030 (7)0.122 (16)
C180.36 (2)0.155 (11)0.173 (13)0.037 (12)0.018 (12)0.008 (9)
C190.386 (19)0.404 (19)0.206 (12)0.314 (17)0.160 (13)0.208 (14)
Geometric parameters (Å, º) top
Cu—O11.928 (2)C4—C51.430 (5)
Cu—N22.031 (3)C5—C61.358 (5)
Cu—N12.042 (3)C6—C71.423 (5)
Cu—Cl2.2781 (9)C6—H41.05 (4)
Cu—Cli2.7248 (11)C7—C81.395 (5)
Cl—Cui2.7248 (11)C7—C111.407 (5)
O1—C131.267 (5)C8—C91.362 (5)
O2—C131.230 (4)C8—H50.91 (4)
O3—N31.190 (5)C9—C101.391 (5)
O4—N31.188 (5)C9—H60.91 (4)
O5—C171.30 (2)C10—H71.02 (4)
N1—C11.318 (5)C11—C121.440 (5)
N1—C121.343 (4)C13—C141.502 (5)
N2—C101.334 (4)C14—C161.375 (5)
N2—C111.343 (4)C14—C151.392 (5)
N3—C51.500 (5)C15—C16ii1.368 (6)
N4—C171.145 (12)C15—H81.01 (4)
N4—C191.418 (10)C16—C15ii1.368 (6)
N4—C181.423 (12)C16—H90.91 (4)
C1—C21.395 (6)C17—H170.9300
C1—H10.99 (3)C18—H18A0.9600
C2—C31.352 (6)C18—H18B0.9600
C2—H20.91 (5)C18—H18C0.9600
C3—C41.396 (5)C19—H19A0.9600
C3—H30.92 (5)C19—H19B0.9600
C4—C121.418 (5)C19—H19C0.9600
O1—Cu—N2171.33 (10)C11—C7—C6118.7 (3)
O1—Cu—N192.19 (11)C9—C8—C7119.2 (3)
N2—Cu—N179.82 (11)C9—C8—H5125 (3)
O1—Cu—Cl93.53 (8)C7—C8—H5115 (3)
N2—Cu—Cl93.95 (8)C8—C9—C10119.7 (3)
N1—Cu—Cl170.34 (8)C8—C9—H6124 (3)
O1—Cu—Cli95.33 (8)C10—C9—H6115 (3)
N2—Cu—Cli88.71 (8)N2—C10—C9122.7 (3)
N1—Cu—Cli94.63 (8)N2—C10—H7116 (2)
Cl—Cu—Cli92.59 (3)C9—C10—H7122 (2)
Cu—Cl—Cui87.41 (3)N2—C11—C7123.2 (3)
C13—O1—Cu113.3 (2)N2—C11—C12116.4 (3)
C1—N1—C12118.5 (3)C7—C11—C12120.5 (3)
C1—N1—Cu127.3 (3)N1—C12—C4123.8 (3)
C12—N1—Cu114.2 (2)N1—C12—C11115.4 (3)
C10—N2—C11117.7 (3)C4—C12—C11120.8 (3)
C10—N2—Cu128.2 (2)O2—C13—O1124.4 (4)
C11—N2—Cu114.0 (2)O2—C13—C14119.3 (4)
O4—N3—O3122.6 (4)O1—C13—C14116.3 (3)
O4—N3—C5119.8 (4)C16—C14—C15117.7 (4)
O3—N3—C5117.6 (4)C16—C14—C13120.8 (3)
C17—N4—C19125.4 (16)C15—C14—C13121.5 (4)
C17—N4—C18117.8 (15)C16ii—C15—C14120.9 (4)
C19—N4—C18116.8 (10)C16ii—C15—H8117 (3)
N1—C1—C2121.6 (4)C14—C15—H8122 (3)
N1—C1—H1115.7 (18)C15ii—C16—C14121.4 (4)
C2—C1—H1122.6 (18)C15ii—C16—H9117 (3)
C3—C2—C1120.4 (4)C14—C16—H9121 (3)
C3—C2—H2131 (3)N4—C17—O5128 (2)
C1—C2—H2109 (3)N4—C17—H17115.9
C2—C3—C4120.1 (4)O5—C17—H17115.9
C2—C3—H3131 (3)N4—C18—H18A109.5
C4—C3—H3108 (3)N4—C18—H18B109.5
C3—C4—C12115.6 (4)H18A—C18—H18B109.5
C3—C4—C5128.8 (3)N4—C18—H18C109.5
C12—C4—C5115.6 (3)H18A—C18—H18C109.5
C6—C5—C4124.7 (3)H18B—C18—H18C109.5
C6—C5—N3113.5 (3)N4—C19—H19A109.5
C4—C5—N3121.8 (3)N4—C19—H19B109.5
C5—C6—C7119.8 (3)H19A—C19—H19B109.5
C5—C6—H4115 (2)N4—C19—H19C109.5
C7—C6—H4125 (2)H19A—C19—H19C109.5
C8—C7—C11117.5 (3)H19B—C19—H19C109.5
C8—C7—C6123.9 (3)
O1—Cu—Cl—Cui95.51 (8)C6—C7—C8—C9178.7 (4)
N2—Cu—Cl—Cui88.88 (8)C7—C8—C9—C100.2 (6)
Cli—Cu—Cl—Cui0.0C11—N2—C10—C92.4 (6)
N1—Cu—O1—C1387.5 (3)Cu—N2—C10—C9178.4 (3)
Cl—Cu—O1—C1384.7 (2)C8—C9—C10—N21.2 (6)
Cli—Cu—O1—C13177.7 (2)C10—N2—C11—C72.2 (5)
O1—Cu—N1—C11.6 (3)Cu—N2—C11—C7178.7 (3)
N2—Cu—N1—C1178.2 (3)C10—N2—C11—C12179.5 (3)
Cli—Cu—N1—C193.9 (3)Cu—N2—C11—C122.9 (4)
O1—Cu—N1—C12179.8 (2)C8—C7—C11—N20.8 (5)
N2—Cu—N1—C123.6 (2)C6—C7—C11—N2180.0 (3)
Cli—Cu—N1—C1284.2 (2)C8—C7—C11—C12179.1 (3)
N1—Cu—N2—C10179.6 (3)C6—C7—C11—C121.7 (5)
Cl—Cu—N2—C107.8 (3)C1—N1—C12—C41.4 (5)
Cli—Cu—N2—C1084.7 (3)Cu—N1—C12—C4177.0 (3)
N1—Cu—N2—C113.5 (2)C1—N1—C12—C11178.5 (3)
Cl—Cu—N2—C11176.1 (2)Cu—N1—C12—C113.1 (4)
Cli—Cu—N2—C1191.4 (2)C3—C4—C12—N11.0 (5)
C12—N1—C1—C20.3 (6)C5—C4—C12—N1180.0 (3)
Cu—N1—C1—C2177.8 (3)C3—C4—C12—C11178.9 (3)
N1—C1—C2—C31.1 (7)C5—C4—C12—C110.2 (5)
C1—C2—C3—C41.4 (7)N2—C11—C12—N10.1 (5)
C2—C3—C4—C120.4 (6)C7—C11—C12—N1178.2 (3)
C2—C3—C4—C5178.4 (4)N2—C11—C12—C4180.0 (3)
C3—C4—C5—C6176.9 (4)C7—C11—C12—C41.6 (5)
C12—C4—C5—C62.0 (6)Cu—O1—C13—O23.1 (5)
C3—C4—C5—N33.8 (6)Cu—O1—C13—C14177.5 (2)
C12—C4—C5—N3177.3 (3)O2—C13—C14—C1610.2 (6)
O4—N3—C5—C615.5 (6)O1—C13—C14—C16170.4 (4)
O3—N3—C5—C6163.3 (4)O2—C13—C14—C15170.6 (4)
O4—N3—C5—C4163.9 (4)O1—C13—C14—C158.8 (5)
O3—N3—C5—C417.3 (6)C16—C14—C15—C16ii0.4 (7)
C4—C5—C6—C72.0 (6)C13—C14—C15—C16ii179.6 (4)
N3—C5—C6—C7177.4 (3)C15—C14—C16—C15ii0.4 (7)
C5—C6—C7—C8179.1 (4)C13—C14—C16—C15ii179.6 (4)
C5—C6—C7—C110.0 (5)C19—N4—C17—O5178.9 (10)
C11—C7—C8—C90.5 (6)C18—N4—C17—O52.0 (17)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
 

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