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In the title compound, {[Cu(C8H4O4)(C14H8N4)(H2O)]·C3H7NO·H2O}n, the CuII atom binds a water mol­ecule and is chelated by the pyrazinophenanthroline N-heterocycle. It is also linked covalently to an isophthalate dianion that lies on a special position of site symmetry 2. The dianion serves as a spacer that connects adjacent square-pyramidal metal atoms into a zigzag chain propagating along the c axis of the ortho­rhom­bic unit cell. The chain motif is consolidated into a layer structure by hydrogen bonds involving both the coordinated and uncoordinated water mol­ecules. The copper atom and the coordinated water mol­ecule lie on a mirror plane, while the N-heterocycle, the disordered uncoordinated water mol­ecule and the disordered dimethyl­formamide solvent mol­ecule lie across a mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045107/sj2148sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045107/sj2148Isup2.hkl
Contains datablock I

CCDC reference: 630467

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.107
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.552 0.845 Tmin(prime) and Tmax expected: 0.819 0.840 RR(prime) = 0.670 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67 PLAT417_ALERT_2_B Short Inter D-H..H-D H1W2 .. H2W2 .. 1.95 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H1W2 .. H2W2 .. 1.95 Ang.
Alert level C 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 ............ 0.50 Ratio PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT415_ALERT_2_C Short Inter D-H..H-X H1W1 .. H14C .. 2.11 Ang. PLAT415_ALERT_2_C Short Inter D-H..H-X H1W1 .. H14C .. 2.11 Ang. PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... O1<I>W< CU1 O1<I>W< PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... O1<I>W< O1 CU1 O1<I>W< PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... O1<I>W< O1<I>W<CU1 N1 PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... O1<I>W< PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... O1<I>W< PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... O2<I>W< PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

catena-Poly[[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ2N,N')copper(II)]- µ-isophthalato-κ2O:O'] N,N-dimethylformamide solvate monohydrate] top
Crystal data top
[Cu(C8H4O4)(C14H8N4)(H2O)]·C3H7NO·H2OF(000) = 1172
Mr = 569.02Dx = 1.579 Mg m3
Orthorhombic, PbcmMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2bCell parameters from 14093 reflections
a = 7.237 (2) Åθ = 3.3–27.5°
b = 23.877 (6) ŵ = 0.97 mm1
c = 13.848 (8) ÅT = 293 K
V = 2393 (2) Å3Block, blue
Z = 40.20 × 0.19 × 0.18 mm
Data collection top
Rigaku RAXIS-RAPID IP
diffractometer
2810 independent reflections
Radiation source: fine-focus sealed tube2138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.552, Tmax = 0.845k = 3030
20300 measured reflectionsl = 1717
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0575P)2 + 0.5178P]
where P = (Fo2 + 2Fc2)/3
2810 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 0.32 e Å3
57 restraintsΔρmin = 0.46 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.15835 (5)0.076495 (14)0.75000.03864 (15)
O10.0938 (3)0.12947 (6)0.84985 (15)0.0547 (5)
O20.3681 (2)0.16345 (7)0.89469 (14)0.0515 (5)
O1w0.1417 (3)0.04030 (10)0.75000.0598 (8)
H1w10.170 (4)0.0059 (5)0.75000.072*
H1w20.239 (3)0.0599 (11)0.75000.072*
O2w0.5377 (5)0.10369 (14)0.758 (3)0.061 (4)0.50
H2w10.483 (7)0.121 (2)0.803 (4)0.074*0.50
H2w20.610 (7)0.1262 (17)0.729 (4)0.074*0.50
N10.2360 (3)0.01659 (7)0.65507 (13)0.0358 (4)
N20.4488 (3)0.17407 (7)0.64883 (16)0.0481 (5)
C10.1976 (4)0.16395 (8)0.89414 (17)0.0396 (5)
C20.0947 (3)0.20856 (8)0.94985 (16)0.0343 (5)
C30.1893 (4)0.25001.00000.0340 (6)
H30.31780.25001.00000.041*
C40.0977 (3)0.20896 (9)0.94993 (18)0.0428 (6)
H40.16270.18160.91630.051*
C50.1920 (5)0.25001.00000.0467 (8)
H50.32050.25001.00000.056*
C60.2971 (3)0.03074 (8)0.69834 (14)0.0315 (4)
C70.3516 (3)0.07805 (8)0.64667 (16)0.0355 (5)
C80.3434 (4)0.07574 (10)0.54579 (19)0.0518 (7)
H80.38100.10610.50860.062*
C90.2792 (5)0.02815 (11)0.5029 (2)0.0622 (8)
H90.27060.02610.43600.075*
C100.2269 (4)0.01721 (10)0.55919 (18)0.0511 (6)
H100.18380.04930.52860.061*
C110.4055 (3)0.12784 (8)0.69982 (17)0.0363 (5)
C120.4878 (3)0.21934 (9)0.70064 (18)0.0514 (6)
H120.51620.25240.66840.062*
O30.1821 (6)0.06183 (15)0.8352 (3)0.0617 (11)0.50
N30.0919 (4)0.13586 (14)0.7437 (12)0.0413 (13)0.50
C130.1257 (10)0.1112 (4)0.8290 (11)0.045 (2)0.50
H130.10650.13150.88540.054*0.50
C140.1198 (17)0.1065 (5)0.6538 (12)0.059 (4)0.50
H14A0.22810.12090.62230.089*0.50
H14B0.01430.11190.61280.089*0.50
H14C0.13570.06730.66640.089*0.50
C150.0273 (6)0.19346 (16)0.7409 (18)0.056 (2)0.50
H15A0.08560.19660.77680.084*0.50
H15B0.00580.20430.67510.084*0.50
H15C0.11910.21750.76890.084*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0574 (3)0.0203 (2)0.0382 (3)0.00113 (15)0.0000.000
O10.0665 (11)0.0318 (8)0.0658 (14)0.0000 (7)0.0039 (9)0.0186 (8)
O20.0560 (11)0.0423 (10)0.0561 (13)0.0046 (7)0.0052 (8)0.0119 (8)
O1w0.0490 (14)0.0374 (13)0.093 (2)0.0014 (10)0.0000.000
O2w0.066 (2)0.066 (2)0.052 (12)0.0236 (14)0.003 (5)0.016 (8)
N10.0490 (11)0.0277 (9)0.0307 (11)0.0018 (7)0.0010 (8)0.0029 (7)
N20.0607 (12)0.0331 (10)0.0504 (14)0.0043 (8)0.0087 (10)0.0056 (9)
C10.0644 (16)0.0223 (10)0.0320 (14)0.0001 (9)0.0013 (11)0.0014 (8)
C20.0509 (12)0.0239 (10)0.0281 (12)0.0010 (8)0.0008 (10)0.0016 (8)
C30.0434 (16)0.0262 (14)0.0324 (17)0.0000.0000.0021 (12)
C40.0515 (13)0.0328 (12)0.0442 (15)0.0085 (9)0.0048 (11)0.0016 (10)
C50.0442 (18)0.0465 (19)0.050 (2)0.0000.0000.0021 (16)
C60.0379 (10)0.0282 (10)0.0286 (11)0.0044 (8)0.0007 (9)0.0001 (8)
C70.0456 (12)0.0305 (11)0.0306 (13)0.0012 (8)0.0016 (9)0.0020 (8)
C80.083 (2)0.0385 (13)0.0337 (15)0.0029 (12)0.0070 (12)0.0059 (10)
C90.111 (2)0.0489 (15)0.0265 (14)0.0036 (15)0.0004 (15)0.0008 (11)
C100.0817 (18)0.0369 (13)0.0346 (15)0.0052 (11)0.0057 (13)0.0060 (10)
C110.0381 (11)0.0282 (10)0.0426 (13)0.0008 (8)0.0041 (10)0.0023 (9)
C120.0581 (14)0.0305 (11)0.0655 (17)0.0079 (10)0.0066 (12)0.0052 (10)
O30.092 (3)0.0386 (18)0.055 (2)0.0031 (18)0.017 (2)0.0047 (17)
N30.0508 (16)0.0376 (15)0.036 (4)0.0020 (12)0.007 (4)0.003 (5)
C130.056 (5)0.040 (4)0.040 (5)0.019 (3)0.000 (3)0.002 (3)
C140.071 (6)0.058 (5)0.050 (7)0.004 (4)0.001 (4)0.010 (4)
C150.056 (2)0.0413 (19)0.071 (7)0.0001 (16)0.007 (5)0.005 (4)
Geometric parameters (Å, º) top
Cu1—O11.931 (2)C6—C71.394 (3)
Cu1—O1i1.931 (2)C6—C6i1.431 (4)
Cu1—N1i2.022 (2)C7—C81.399 (3)
Cu1—N12.022 (2)C7—C111.452 (3)
Cu1—O1w2.337 (2)C8—C91.364 (3)
O1—C11.272 (3)C8—H80.9300
O2—C11.234 (3)C9—C101.387 (3)
O1w—H1w10.85 (1)C9—H90.9300
O1w—H1w20.85 (1)C10—H100.9300
O2w—H2w10.85 (1)C11—C11i1.390 (5)
O2w—H2w20.85 (1)C12—C12i1.367 (5)
N1—C101.329 (3)C12—H120.9300
N1—C61.353 (2)O3—C131.250 (8)
N2—C121.328 (3)N3—C131.342 (8)
N2—C111.347 (3)N3—C141.442 (8)
C1—C21.511 (3)N3—C151.453 (5)
C2—C31.389 (3)C13—H130.9300
C2—C41.392 (3)C14—H14A0.9600
C3—C2ii1.389 (2)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C4—C51.381 (3)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C4ii1.381 (3)C15—H15C0.9600
C5—H50.9300
O1—Cu1—O1i91.4 (1)C6—C7—C11118.6 (2)
O1—Cu1—N1174.8 (1)C8—C7—C11123.4 (2)
O1—Cu1—N1i93.7 (1)C9—C8—C7118.8 (2)
O1—Cu1—O1w91.0 (1)C9—C8—H8120.6
O1w—Cu1—N189.8 (1)C7—C8—H8120.6
O1w—Cu1—N1i89.8 (1)C8—C9—C10119.9 (3)
N1—Cu1—N1i81.1 (1)C8—C9—H9120.0
C1—O1—Cu1128.79 (17)C10—C9—H9120.0
Cu1—O1w—H1w1126 (2)N1—C10—C9122.6 (2)
Cu1—O1w—H1w2125 (2)N1—C10—H10118.7
H1w1—O1w—H1w2109 (2)C9—C10—H10118.7
H2w1—O2w—H2w2109 (2)N2—C11—C11i121.61 (14)
C10—N1—C6117.88 (19)N2—C11—C7117.9 (2)
C10—N1—Cu1128.87 (16)C11i—C11—C7120.47 (12)
C6—N1—Cu1113.18 (14)N2—C12—C12i122.71 (14)
C12—N2—C11115.7 (2)N2—C12—H12118.6
O2—C1—O1126.0 (2)C12i—C12—H12118.6
O2—C1—C2119.7 (2)C13—N3—C14121.4 (4)
O1—C1—C2114.3 (2)C13—N3—C15119.8 (11)
C3—C2—C4119.2 (2)C14—N3—C15118.8 (11)
C3—C2—C1121.0 (2)O3—C13—N3122.3 (9)
C4—C2—C1119.9 (2)O3—C13—H13118.8
C2—C3—C2ii121.0 (3)N3—C13—H13118.8
C2—C3—H3119.5N3—C14—H14A109.5
C2ii—C3—H3119.5N3—C14—H14B109.5
C5—C4—C2120.0 (2)H14A—C14—H14B109.5
C5—C4—H4120.0N3—C14—H14C109.5
C2—C4—H4120.0H14A—C14—H14C109.5
C4ii—C5—C4120.8 (3)H14B—C14—H14C109.5
C4ii—C5—H5119.6N3—C15—H15A109.5
C4—C5—H5119.6N3—C15—H15B109.5
N1—C6—C7122.81 (19)H15A—C15—H15B109.5
N1—C6—C6i116.28 (11)N3—C15—H15C109.5
C7—C6—C6i120.88 (12)H15A—C15—H15C109.5
C6—C7—C8117.9 (2)H15B—C15—H15C109.5
O1i—Cu1—O1—C193.6 (2)C10—N1—C6—C6i177.28 (17)
N1i—Cu1—O1—C185.5 (2)Cu1—N1—C6—C6i0.07 (15)
O1w—Cu1—O1—C1175.4 (2)N1—C6—C7—C80.5 (3)
O1i—Cu1—N1—C103.9 (2)C6i—C6—C7—C8178.24 (16)
N1i—Cu1—N1—C10176.91 (19)N1—C6—C7—C11176.67 (19)
O1w—Cu1—N1—C1087.1 (2)C6i—C6—C7—C111.1 (2)
O1i—Cu1—N1—C6179.25 (15)C6—C7—C8—C91.4 (4)
N1i—Cu1—N1—C60.08 (17)C11—C7—C8—C9175.6 (2)
O1w—Cu1—N1—C689.75 (14)C7—C8—C9—C101.2 (4)
Cu1—O1—C1—O214.3 (4)C6—N1—C10—C90.7 (4)
Cu1—O1—C1—C2165.69 (15)Cu1—N1—C10—C9177.5 (2)
O2—C1—C2—C31.6 (3)C8—C9—C10—N10.1 (5)
O1—C1—C2—C3178.45 (17)C12—N2—C11—C11i1.2 (3)
O2—C1—C2—C4179.5 (2)C12—N2—C11—C7176.6 (2)
O1—C1—C2—C40.5 (3)C6—C7—C11—N2176.71 (19)
C4—C2—C3—C2ii0.22 (15)C8—C7—C11—N20.3 (3)
C1—C2—C3—C2ii179.1 (2)C6—C7—C11—C11i1.1 (2)
C3—C2—C4—C50.4 (3)C8—C7—C11—C11i178.07 (17)
C1—C2—C4—C5179.37 (17)C11—N2—C12—C12i1.2 (3)
C2—C4—C5—C4ii0.22 (15)C14—N3—C13—O30.3 (3)
C10—N1—C6—C70.6 (3)C15—N3—C13—O3179.7 (3)
Cu1—N1—C6—C7177.78 (15)
Symmetry codes: (i) x, y, z+3/2; (ii) x, y+1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O30.85 (1)2.00 (1)2.725 (4)142 (1)
O1w—H1w2···O2wiii0.85 (1)1.93 (1)2.773 (5)177 (2)
O2w—H2w1···O20.85 (1)1.82 (4)2.67 (3)175 (6)
Symmetry code: (iii) x1, y, z.
 

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