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In the title compound, [Cu(C8H4O4)(C14H8N4)(H2O)]·C3H7NO·H2O, the CuII atom binds a water mol­ecule and is chelated by the pyrazinophenanthroline N-heterocycle. It is also linked covalently to a terephthalate dianion that lies on a special position of \overline{1} site symmetry. This dianion serves as a spacer to connect adjacent square-pyramidal metal atoms into a helical chain that propagates along the b axis of the monoclinic unit cell. The chain motif is consolidated into a layer structure by hydrogen bonds involving the coordinated and uncoordinated water mol­ecules. The Cu atom and the coordinated water mol­ecule lie on a mirror plane, while the N-heterocycle, the disordered uncoordinated water mol­ecule and disordered dimethyl­formamide solvent molecule lie about a mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044928/sj2147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044928/sj2147Isup2.hkl
Contains datablock I

CCDC reference: 630466

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.050
  • wR factor = 0.144
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity. PLAT780_ALERT_1_A Coordinates do not Form a Properly Connected Set ?
Alert level B PLAT415_ALERT_2_B Short Inter D-H..H-X H1W1 .. H13C .. 2.03 Ang. PLAT415_ALERT_2_B Short Inter D-H..H-X H1W1 .. H13C .. 2.03 Ang. PLAT416_ALERT_2_B Short Intra D-H..H-D H1W2 .. H2W2 .. 1.86 Ang. PLAT416_ALERT_2_B Short Intra D-H..H-D H1W2 .. H2W2 .. 1.86 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.701 0.909 Tmin(prime) and Tmax expected: 0.811 0.908 RR(prime) = 0.863 Please check that your absorption correction is appropriate. 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 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1197.00 Ang-3 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H2# 1.555 1.555
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
3 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 13 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 6 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-terephthalato-κ2O:O'] N,N-dimethylformamide monohydrate] top
Crystal data top
[Cu(C8H4O4)(C14H8N4)(H2O)]·C3H7NO·H2OF(000) = 586
Mr = 569.02Dx = 1.578 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 9444 reflections
a = 7.275 (4) Åθ = 3.2–27.5°
b = 13.970 (5) ŵ = 0.97 mm1
c = 11.794 (5) ÅT = 293 K
β = 92.78 (2)°Block, green
V = 1197 (1) Å30.21 × 0.19 × 0.10 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
2856 independent reflections
Radiation source: fine-focus sealed tube2229 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.701, Tmax = 0.909k = 1618
11896 measured reflectionsl = 1514
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.077P)2 + 0.8938P]
where P = (Fo2 + 2Fc2)/3
2856 reflections(Δ/σ)max = 0.001
214 parametersΔρmax = 0.85 e Å3
58 restraintsΔρmin = 0.56 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.35210 (8)0.25000.64318 (4)0.0386 (2)
O10.4201 (4)0.3484 (2)0.7528 (2)0.0575 (7)
O20.1446 (4)0.3936 (2)0.8086 (2)0.0617 (8)
O1W0.6390 (5)0.25000.5738 (3)0.0607 (11)
H1W10.662 (7)0.25000.5043 (13)0.073*
H1W20.738 (4)0.25000.614 (4)0.073*
O2W0.9645 (8)0.260 (4)0.6961 (5)0.070 (7)0.50
H2W11.036 (10)0.302 (6)0.726 (7)0.084*0.50
H2W20.889 (10)0.242 (9)0.745 (5)0.084*0.50
N10.2637 (4)0.34436 (18)0.5218 (2)0.0375 (6)
N20.0266 (5)0.3496 (3)0.1299 (3)0.0635 (10)
C10.3144 (5)0.3923 (2)0.8172 (3)0.0433 (8)
C20.4119 (5)0.4492 (2)0.9116 (2)0.0371 (7)
C30.6013 (5)0.4521 (2)0.9218 (3)0.0429 (8)
H30.67010.42000.86930.051*
C40.6901 (5)0.5024 (2)1.0098 (3)0.0419 (7)
H40.81800.50391.01610.050*
C50.1969 (4)0.30106 (19)0.4258 (2)0.0328 (6)
C60.1358 (4)0.3528 (2)0.3294 (3)0.0406 (7)
C70.1431 (6)0.4526 (3)0.3350 (3)0.0565 (10)
H70.10100.48940.27340.068*
C80.2127 (7)0.4954 (3)0.4321 (3)0.0641 (12)
H80.22060.56180.43650.077*
C90.2720 (6)0.4390 (2)0.5243 (3)0.0523 (9)
H90.31890.46900.58990.063*
C100.0781 (5)0.2997 (2)0.2291 (2)0.0434 (8)
C110.0069 (5)0.2992 (2)0.0540 (3)0.0437 (8)
H110.03740.32860.01510.052*
O50.6708 (10)0.1582 (4)0.3734 (5)0.0651 (17)0.50
N30.5780 (5)0.2533 (16)0.2253 (4)0.0453 (12)0.50
C120.6065 (15)0.1672 (18)0.2728 (10)0.050 (4)0.50
H120.57820.11260.23040.060*0.50
C130.622 (2)0.3392 (17)0.2888 (12)0.054 (4)0.50
H13A0.50980.37050.30790.080*0.50
H13B0.69250.38130.24380.080*0.50
H13C0.69170.32290.35720.080*0.50
C140.5053 (9)0.2628 (15)0.1094 (5)0.055 (3)0.50
H14A0.59760.29010.06370.082*0.50
H14B0.39920.30380.10750.082*0.50
H14C0.47090.20090.08020.082*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0572 (4)0.0337 (3)0.0237 (3)0.0000.0115 (2)0.000
O10.0702 (18)0.0646 (17)0.0363 (12)0.0002 (14)0.0127 (12)0.0222 (12)
O20.0586 (19)0.0634 (18)0.0611 (16)0.0045 (13)0.0199 (13)0.0174 (14)
O1W0.043 (2)0.096 (3)0.042 (2)0.0000.0104 (16)0.000
O2W0.071 (3)0.04 (2)0.094 (4)0.009 (7)0.046 (3)0.000 (5)
N10.0464 (16)0.0332 (13)0.0321 (13)0.0022 (11)0.0057 (11)0.0004 (10)
N20.059 (2)0.070 (2)0.062 (2)0.0172 (17)0.0069 (17)0.0347 (19)
C10.063 (2)0.0354 (16)0.0301 (15)0.0047 (15)0.0139 (15)0.0002 (12)
C20.0499 (19)0.0323 (15)0.0279 (14)0.0018 (13)0.0101 (13)0.0006 (11)
C30.055 (2)0.0411 (18)0.0320 (15)0.0001 (15)0.0023 (14)0.0053 (13)
C40.0433 (19)0.0434 (18)0.0384 (16)0.0021 (14)0.0059 (14)0.0036 (13)
C50.0315 (15)0.0406 (16)0.0258 (13)0.0017 (12)0.0026 (11)0.0037 (12)
C60.0361 (17)0.0518 (19)0.0338 (15)0.0054 (14)0.0001 (13)0.0084 (14)
C70.071 (3)0.048 (2)0.051 (2)0.0125 (18)0.0009 (19)0.0167 (17)
C80.100 (4)0.0336 (18)0.059 (2)0.006 (2)0.002 (2)0.0102 (17)
C90.077 (3)0.0325 (17)0.0471 (19)0.0009 (17)0.0033 (18)0.0013 (14)
C100.0347 (17)0.070 (2)0.0246 (14)0.0052 (15)0.0043 (12)0.0070 (14)
C110.0313 (17)0.0469 (19)0.053 (2)0.0046 (14)0.0034 (15)0.0080 (16)
O50.095 (5)0.050 (3)0.049 (3)0.014 (3)0.002 (3)0.003 (2)
N30.048 (2)0.043 (3)0.045 (2)0.003 (8)0.0017 (18)0.003 (8)
C120.056 (7)0.058 (8)0.038 (5)0.001 (5)0.009 (5)0.003 (5)
C130.062 (7)0.042 (6)0.056 (7)0.003 (5)0.004 (5)0.001 (6)
C140.054 (3)0.059 (10)0.051 (3)0.001 (5)0.002 (3)0.006 (4)
Geometric parameters (Å, º) top
Cu1—O11.934 (2)C5—C5i1.426 (5)
Cu1—O1i1.934 (2)C6—C71.396 (5)
Cu1—N12.028 (3)C6—C101.442 (4)
Cu1—N1i2.028 (3)C7—C81.368 (5)
Cu1—O1W2.279 (4)C7—H70.9300
O1—C11.265 (4)C8—C91.394 (5)
O2—C11.235 (5)C8—H80.9300
O1W—H1W10.84 (1)C9—H90.9300
O1W—H1W20.85 (1)C10—C10i1.388 (6)
O2W—H2W10.85 (1)C11—C11i1.374 (6)
O2W—H2W20.86 (1)C11—H110.9300
N1—C91.324 (4)O5—C121.261 (10)
N1—C51.353 (3)N3—C121.338 (9)
N2—C111.156 (5)N3—C131.442 (9)
N2—C101.397 (4)N3—C141.448 (6)
C1—C21.516 (4)C12—H120.9300
C2—C31.378 (5)C13—H13A0.9600
C2—C4ii1.391 (5)C13—H13B0.9600
C3—C41.387 (4)C13—H13C0.9600
C3—H30.9300C14—H14A0.9600
C4—C2ii1.391 (5)C14—H14B0.9600
C4—H40.9300C14—H14C0.9600
C5—C61.401 (4)
O1—Cu1—O1i90.5 (2)C8—C7—C6119.2 (3)
O1—Cu1—O1W91.8 (2)C8—C7—H7120.4
O1—Cu1—N194.1 (1)C6—C7—H7120.4
O1—Cu1—N1i174.7 (1)C7—C8—C9119.6 (3)
O1W—Cu1—N190.6 (1)C7—C8—H8120.2
O1W—Cu1—N1i90.6 (1)C9—C8—H8120.2
N1—Cu1—N1i81.1 (1)N1—C9—C8122.3 (3)
C1—O1—Cu1127.1 (3)N1—C9—H9118.8
Cu1—O1W—H1W1125 (4)C8—C9—H9118.8
Cu1—O1W—H1W2125 (3)C10i—C10—N2119.9 (2)
H1W1—O1W—H1W2110 (2)C10i—C10—C6120.97 (17)
H2W1—O2W—H2W2109 (2)N2—C10—C6119.1 (3)
C9—N1—C5118.7 (3)N2—C11—C11i127.5 (2)
C9—N1—Cu1128.4 (2)N2—C11—H11116.2
C5—N1—Cu1112.88 (19)C11i—C11—H11116.2
C11—N2—C10112.5 (4)C12—N3—C13120.3 (5)
O2—C1—O1126.3 (3)C12—N3—C14121.3 (11)
O2—C1—C2118.9 (3)C13—N3—C14118.4 (11)
O1—C1—C2114.8 (3)O5—C12—N3121.8 (15)
C3—C2—C4ii119.4 (3)O5—C12—H12119.1
C3—C2—C1120.6 (3)N3—C12—H12119.1
C4ii—C2—C1119.9 (3)N3—C13—H13A109.5
C2—C3—C4120.5 (3)N3—C13—H13B109.5
C2—C3—H3119.7H13A—C13—H13B109.5
C4—C3—H3119.7N3—C13—H13C109.5
C3—C4—C2ii120.1 (3)H13A—C13—H13C109.5
C3—C4—H4120.0H13B—C13—H13C109.5
C2ii—C4—H4120.0N3—C14—H14A109.5
N1—C5—C6122.4 (3)N3—C14—H14B109.5
N1—C5—C5i116.57 (15)H14A—C14—H14B109.5
C6—C5—C5i121.04 (18)N3—C14—H14C109.5
C7—C6—C5117.8 (3)H14A—C14—H14C109.5
C7—C6—C10124.1 (3)H14B—C14—H14C109.5
C5—C6—C10118.0 (3)
O1i—Cu1—O1—C195.8 (3)Cu1—N1—C5—C5i0.8 (2)
N1—Cu1—O1—C181.6 (3)N1—C5—C6—C70.9 (5)
O1W—Cu1—O1—C1172.4 (3)C5i—C5—C6—C7178.8 (3)
O1—Cu1—N1—C94.8 (3)N1—C5—C6—C10176.1 (3)
N1i—Cu1—N1—C9177.6 (3)C5i—C5—C6—C101.8 (4)
O1W—Cu1—N1—C987.1 (3)C5—C6—C7—C81.6 (6)
O1—Cu1—N1—C5178.6 (2)C10—C6—C7—C8175.2 (4)
N1i—Cu1—N1—C50.9 (3)C6—C7—C8—C91.2 (7)
O1W—Cu1—N1—C589.6 (2)C5—N1—C9—C80.6 (6)
Cu1—O1—C1—O214.0 (5)Cu1—N1—C9—C8177.1 (3)
Cu1—O1—C1—C2167.1 (2)C7—C8—C9—N10.1 (7)
O2—C1—C2—C3177.9 (3)C11—N2—C10—C10i2.2 (4)
O1—C1—C2—C31.1 (4)C11—N2—C10—C6176.0 (3)
O2—C1—C2—C4ii3.4 (5)C7—C6—C10—C10i178.6 (3)
O1—C1—C2—C4ii177.6 (3)C5—C6—C10—C10i1.8 (4)
C4ii—C2—C3—C40.2 (5)C7—C6—C10—N20.4 (5)
C1—C2—C3—C4178.5 (3)C5—C6—C10—N2176.4 (3)
C2—C3—C4—C2ii0.2 (5)C10—N2—C11—C11i2.4 (4)
C9—N1—C5—C60.2 (5)C13—N3—C12—O50.3 (3)
Cu1—N1—C5—C6177.2 (2)C14—N3—C12—O5179.6 (3)
C9—N1—C5—C5i177.8 (3)
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O50.84 (1)2.01 (1)2.708 (7)140 (1)
O1W—H1W2···O2W0.85 (1)1.87 (1)2.716 (7)175 (3)
O2W—H2W1···O2iii0.85 (1)1.77 (5)2.61 (4)167 (9)
Symmetry code: (iii) x+1, y, z.
 

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