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In the crystal structure of the title compound, [CuCl(C12H8N2)2]NO3·C7H5NO4.H2O, the CuII ion assumes a trigonal–bipyramidal CuN4Cl coordination geometry arising from two bidentate 1,10-phenanthroline (phen) ligands and one chloride ion, with the chloride ion in an equatorial position. A partially overlapped arrangement between parallel phen rings of neighboring complexes, with face-to-face distances of 3.529 (9) and 3.452 (8) Å, suggests the existence of π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009529/hb6173sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009529/hb6173Isup2.hkl
Contains datablock I

CCDC reference: 270426

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.045
  • wR factor = 0.110
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N6 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 37.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Chlorobis(1,10-phenanthroline-κ2N,N')copper(II) nitrate 4-nitrobenzoic acid monohydrate top
Crystal data top
[CuCl(C12H8N2)2]NO3·C7H5NO4·H2OZ = 2
Mr = 706.54F(000) = 722
Triclinic, P1Dx = 1.556 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9326 (3) ÅCell parameters from 6517 reflections
b = 11.8986 (4) Åθ = 2.5–27.4°
c = 13.1517 (4) ŵ = 0.88 mm1
α = 82.7790 (11)°T = 295 K
β = 84.4600 (15)°Chunk, blue
γ = 78.7095 (12)°0.34 × 0.21 × 0.13 mm
V = 1508.01 (8) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6855 independent reflections
Radiation source: fine-focus sealed tube5084 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 1.6°
ω scansh = 1212
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1514
Tmin = 0.730, Tmax = 0.888l = 1717
14700 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)] = 0.045Hydrogen site location: difmap (O-H) and geom (C-H, N-H)
wR(F2) = 0.110H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.7183P]
where P = (Fo2 + 2Fc2)/3
6855 reflections(Δ/σ)max = 0.001
453 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.46 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*/UeqOcc. (<1)
Cu0.66401 (3)0.11830 (2)0.67736 (3)0.04476 (11)
Cl0.52248 (7)0.15673 (6)0.54047 (6)0.05734 (19)
O11.0418 (4)0.8728 (3)0.1363 (3)0.1285 (13)
O21.1093 (4)0.7622 (3)0.0190 (3)0.1379 (14)
O30.5919 (2)0.52222 (18)0.34100 (17)0.0689 (6)
H3A0.54270.47650.36940.050*
O40.7013 (3)0.3828 (2)0.2496 (2)0.0951 (9)
O5A0.2255 (9)0.3385 (7)0.3115 (6)0.087 (2)0.68
O6A0.2954 (6)0.4588 (5)0.1952 (4)0.1156 (18)0.68
O7A0.1730 (10)0.3481 (6)0.1562 (7)0.0755 (18)0.68
O5B0.263 (2)0.3207 (16)0.2807 (18)0.143 (9)0.32
O6B0.2017 (17)0.4919 (8)0.2578 (12)0.140 (5)0.32
O7B0.184 (3)0.382 (2)0.141 (2)0.174 (11)0.32
O1W0.4155 (2)0.39902 (18)0.42082 (18)0.0730 (6)
H1A0.35990.37950.37990.050*
H1B0.44840.33490.45110.050*
N10.7851 (2)0.22320 (17)0.60732 (17)0.0445 (5)
N20.8522 (2)0.00514 (17)0.68522 (16)0.0420 (5)
N30.5848 (2)0.21103 (17)0.80313 (17)0.0448 (5)
N40.5475 (2)0.01112 (17)0.75108 (17)0.0456 (5)
N51.0408 (3)0.7870 (3)0.0973 (3)0.0877 (9)
N60.2276 (3)0.3870 (3)0.2214 (3)0.0679 (7)
C10.7481 (3)0.3322 (2)0.5676 (2)0.0540 (7)
H10.65640.36800.57700.065*
C20.8408 (3)0.3944 (2)0.5127 (2)0.0563 (7)
H20.81120.47080.48690.068*
C30.9753 (3)0.3438 (2)0.4966 (2)0.0545 (7)
H31.03760.38470.45880.065*
C41.0188 (2)0.2287 (2)0.5376 (2)0.0453 (6)
C51.1578 (3)0.1671 (3)0.5264 (2)0.0564 (7)
H51.22520.20410.49070.068*
C61.1925 (3)0.0565 (3)0.5668 (2)0.0581 (7)
H61.28340.01850.55830.070*
C71.0924 (2)0.0034 (2)0.6225 (2)0.0469 (6)
C81.1205 (3)0.1193 (2)0.6657 (2)0.0583 (7)
H81.20910.16220.65850.070*
C91.0181 (3)0.1678 (2)0.7176 (2)0.0603 (8)
H91.03660.24380.74740.072*
C100.8841 (3)0.1032 (2)0.7265 (2)0.0509 (6)
H100.81500.13780.76270.061*
C110.9553 (2)0.0547 (2)0.63532 (18)0.0390 (5)
C120.9197 (2)0.1724 (2)0.59265 (18)0.0394 (5)
C130.6072 (3)0.3098 (2)0.8291 (2)0.0566 (7)
H130.67360.34550.79040.068*
C140.5347 (4)0.3619 (3)0.9124 (3)0.0686 (9)
H140.55340.43090.92870.082*
C150.4363 (4)0.3114 (3)0.9700 (2)0.0659 (8)
H150.38670.34631.02500.079*
C160.4106 (3)0.2067 (2)0.9459 (2)0.0522 (7)
C170.3112 (3)0.1458 (3)1.0014 (2)0.0644 (8)
H170.25850.17701.05700.077*
C180.2918 (3)0.0447 (3)0.9755 (2)0.0622 (8)
H180.22610.00731.01320.075*
C190.3712 (3)0.0063 (2)0.8904 (2)0.0524 (7)
C200.3582 (3)0.1123 (3)0.8589 (3)0.0615 (8)
H200.29460.15390.89380.074*
C210.4396 (3)0.1535 (3)0.7771 (3)0.0637 (8)
H210.43350.22440.75700.076*
C220.5317 (3)0.0890 (2)0.7239 (2)0.0569 (7)
H220.58440.11700.66700.068*
C230.4683 (2)0.0522 (2)0.8336 (2)0.0434 (6)
C240.4885 (2)0.1599 (2)0.8620 (2)0.0437 (6)
C250.6879 (3)0.4789 (2)0.2743 (2)0.0606 (8)
C260.7806 (3)0.5602 (2)0.2317 (2)0.0555 (7)
C270.7723 (3)0.6655 (2)0.2682 (2)0.0556 (7)
H270.70830.68650.32220.067*
C280.8580 (3)0.7395 (3)0.2253 (2)0.0604 (7)
H280.85290.81020.24990.072*
C290.9512 (3)0.7066 (3)0.1454 (3)0.0652 (8)
C300.9625 (4)0.6021 (3)0.1091 (3)0.0904 (12)
H301.02680.58120.05530.108*
C310.8780 (4)0.5292 (3)0.1531 (3)0.0857 (11)
H310.88610.45740.12980.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.03598 (16)0.03672 (16)0.0610 (2)0.01108 (12)0.00470 (13)0.00247 (13)
Cl0.0499 (4)0.0525 (4)0.0710 (5)0.0136 (3)0.0149 (3)0.0028 (3)
O10.164 (3)0.148 (3)0.106 (2)0.111 (3)0.006 (2)0.022 (2)
O20.144 (3)0.152 (3)0.123 (3)0.075 (3)0.056 (2)0.016 (2)
O30.0745 (14)0.0540 (12)0.0763 (15)0.0166 (10)0.0102 (12)0.0040 (10)
O40.0972 (18)0.0516 (13)0.136 (2)0.0184 (13)0.0248 (17)0.0264 (14)
O5A0.106 (4)0.099 (6)0.063 (3)0.053 (4)0.009 (3)0.001 (3)
O6A0.163 (5)0.102 (4)0.103 (4)0.094 (4)0.014 (3)0.003 (3)
O7A0.096 (4)0.071 (2)0.067 (4)0.031 (3)0.002 (3)0.014 (2)
O5B0.20 (2)0.048 (6)0.18 (2)0.011 (9)0.106 (16)0.013 (11)
O6B0.196 (14)0.062 (6)0.172 (13)0.018 (7)0.071 (10)0.021 (7)
O7B0.117 (14)0.29 (3)0.081 (12)0.068 (16)0.009 (10)0.049 (17)
O1W0.0798 (15)0.0560 (12)0.0826 (16)0.0174 (11)0.0133 (12)0.0077 (11)
N10.0346 (10)0.0380 (10)0.0605 (14)0.0089 (8)0.0010 (9)0.0018 (9)
N20.0405 (10)0.0378 (10)0.0476 (12)0.0073 (9)0.0031 (9)0.0051 (9)
N30.0443 (11)0.0378 (10)0.0521 (13)0.0091 (9)0.0012 (9)0.0037 (9)
N40.0416 (11)0.0378 (11)0.0580 (14)0.0127 (9)0.0006 (10)0.0008 (9)
N50.083 (2)0.109 (3)0.076 (2)0.040 (2)0.0062 (17)0.007 (2)
N60.0681 (18)0.0607 (18)0.073 (2)0.0199 (16)0.0073 (16)0.0011 (17)
C10.0430 (14)0.0415 (13)0.076 (2)0.0093 (11)0.0039 (13)0.0027 (13)
C20.0603 (17)0.0403 (13)0.0695 (19)0.0177 (12)0.0065 (14)0.0043 (13)
C30.0542 (16)0.0588 (16)0.0544 (17)0.0267 (14)0.0018 (13)0.0008 (13)
C40.0408 (13)0.0537 (14)0.0449 (15)0.0166 (11)0.0014 (11)0.0106 (12)
C50.0393 (13)0.0722 (19)0.0608 (18)0.0193 (13)0.0092 (12)0.0155 (15)
C60.0335 (13)0.073 (2)0.0684 (19)0.0060 (13)0.0045 (12)0.0218 (16)
C70.0391 (13)0.0488 (14)0.0537 (16)0.0020 (11)0.0071 (11)0.0162 (12)
C80.0452 (14)0.0542 (16)0.075 (2)0.0043 (13)0.0136 (14)0.0175 (14)
C90.0627 (18)0.0418 (14)0.074 (2)0.0013 (13)0.0189 (15)0.0041 (14)
C100.0554 (15)0.0422 (13)0.0541 (17)0.0082 (12)0.0060 (12)0.0019 (12)
C110.0354 (11)0.0430 (12)0.0408 (13)0.0079 (10)0.0041 (10)0.0106 (10)
C120.0350 (11)0.0437 (12)0.0416 (14)0.0109 (10)0.0017 (10)0.0081 (10)
C130.0637 (17)0.0472 (15)0.0606 (19)0.0158 (13)0.0025 (14)0.0060 (13)
C140.094 (2)0.0483 (16)0.067 (2)0.0170 (16)0.0012 (18)0.0178 (15)
C150.082 (2)0.0589 (18)0.0515 (18)0.0035 (16)0.0043 (16)0.0091 (14)
C160.0555 (15)0.0532 (15)0.0427 (15)0.0020 (13)0.0032 (12)0.0019 (12)
C170.0586 (17)0.079 (2)0.0465 (17)0.0049 (16)0.0068 (13)0.0079 (15)
C180.0497 (15)0.073 (2)0.0575 (19)0.0146 (14)0.0042 (13)0.0172 (15)
C190.0413 (13)0.0536 (15)0.0589 (17)0.0120 (12)0.0063 (12)0.0147 (13)
C200.0513 (16)0.0588 (17)0.076 (2)0.0263 (14)0.0124 (15)0.0191 (15)
C210.0654 (18)0.0454 (15)0.085 (2)0.0246 (14)0.0164 (17)0.0043 (15)
C220.0559 (16)0.0458 (15)0.071 (2)0.0159 (13)0.0025 (14)0.0054 (13)
C230.0358 (12)0.0420 (13)0.0505 (15)0.0088 (10)0.0058 (11)0.0068 (11)
C240.0389 (12)0.0429 (13)0.0456 (15)0.0032 (10)0.0054 (10)0.0038 (11)
C250.0653 (18)0.0440 (15)0.068 (2)0.0028 (13)0.0069 (15)0.0011 (14)
C260.0582 (16)0.0470 (15)0.0581 (18)0.0030 (13)0.0064 (13)0.0026 (13)
C270.0596 (16)0.0585 (17)0.0495 (17)0.0119 (14)0.0046 (13)0.0068 (13)
C280.0716 (19)0.0601 (17)0.0538 (18)0.0198 (15)0.0146 (15)0.0035 (14)
C290.0592 (18)0.077 (2)0.061 (2)0.0230 (16)0.0057 (15)0.0036 (16)
C300.091 (3)0.083 (3)0.092 (3)0.017 (2)0.031 (2)0.019 (2)
C310.095 (3)0.062 (2)0.096 (3)0.0128 (19)0.026 (2)0.0222 (19)
Geometric parameters (Å, º) top
Cu—Cl2.3359 (8)C7—C111.405 (3)
Cu—N11.985 (2)C7—C81.409 (4)
Cu—N22.0823 (19)C8—C91.353 (4)
Cu—N32.107 (2)C8—H80.9300
Cu—N41.989 (2)C9—C101.403 (4)
O1—N51.201 (4)C9—H90.9300
O2—N51.213 (4)C10—H100.9300
O3—C251.305 (4)C11—C121.431 (3)
O3—H3A0.8324C13—C141.395 (4)
O4—C251.207 (4)C13—H130.9300
O5A—N61.250 (9)C14—C151.365 (5)
O6A—N61.187 (5)C14—H140.9300
O7A—N61.237 (10)C15—C161.399 (4)
O5B—N61.07 (2)C15—H150.9300
O6B—N61.361 (11)C16—C241.395 (4)
O7B—N61.19 (3)C16—C171.429 (4)
O1W—H1A0.8868C17—C181.345 (5)
O1W—H1B0.8363C17—H170.9300
N1—C11.330 (3)C18—C191.434 (4)
N1—C121.361 (3)C18—H180.9300
N2—C101.325 (3)C19—C231.402 (3)
N2—C111.355 (3)C19—C201.408 (4)
N3—C131.328 (3)C20—C211.364 (5)
N3—C241.360 (3)C20—H200.9300
N4—C221.327 (3)C21—C221.390 (4)
N4—C231.362 (3)C21—H210.9300
N5—C291.476 (4)C22—H220.9300
C1—C21.387 (4)C23—C241.434 (4)
C1—H10.9300C25—C261.487 (4)
C2—C31.362 (4)C26—C311.380 (4)
C2—H20.9300C26—C271.382 (4)
C3—C41.407 (4)C27—C281.376 (4)
C3—H30.9300C27—H270.9300
C4—C121.393 (3)C28—C291.374 (4)
C4—C51.435 (4)C28—H280.9300
C5—C61.347 (4)C29—C301.367 (5)
C5—H50.9300C30—C311.363 (5)
C6—C71.428 (4)C30—H300.9300
C6—H60.9300C31—H310.9300
Cl—Cu—N191.45 (7)N2—C11—C7123.7 (2)
Cl—Cu—N2126.90 (6)N2—C11—C12117.0 (2)
Cl—Cu—N3113.78 (6)C7—C11—C12119.3 (2)
Cl—Cu—N490.50 (7)N1—C12—C4123.1 (2)
N1—Cu—N281.21 (8)N1—C12—C11116.2 (2)
N1—Cu—N398.67 (8)C4—C12—C11120.6 (2)
N1—Cu—N4178.01 (9)N3—C13—C14122.4 (3)
N2—Cu—N3119.32 (8)N3—C13—H13118.8
N2—Cu—N497.30 (8)C14—C13—H13118.8
N3—Cu—N480.88 (8)C15—C14—C13119.8 (3)
C25—O3—H3A114.7C15—C14—H14120.1
H1A—O1W—H1B101.5C13—C14—H14120.1
C1—N1—C12117.8 (2)C14—C15—C16119.6 (3)
C1—N1—Cu127.63 (17)C14—C15—H15120.2
C12—N1—Cu114.34 (15)C16—C15—H15120.2
C10—N2—C11117.7 (2)C24—C16—C15116.9 (3)
C10—N2—Cu131.30 (18)C24—C16—C17118.8 (3)
C11—N2—Cu110.96 (15)C15—C16—C17124.3 (3)
C13—N3—C24117.5 (2)C18—C17—C16121.8 (3)
C13—N3—Cu131.54 (19)C18—C17—H17119.1
C24—N3—Cu110.79 (16)C16—C17—H17119.1
C22—N4—C23118.2 (2)C17—C18—C19120.8 (3)
C22—N4—Cu127.3 (2)C17—C18—H18119.6
C23—N4—Cu114.32 (16)C19—C18—H18119.6
O1—N5—O2123.6 (4)C23—C19—C20117.0 (3)
O1—N5—C29119.1 (4)C23—C19—C18118.7 (3)
O2—N5—C29117.3 (4)C20—C19—C18124.3 (3)
O5B—N6—O7B131.3 (18)C21—C20—C19119.6 (3)
O6A—N6—O7A119.6 (5)C21—C20—H20120.2
O6A—N6—O5A121.1 (6)C19—C20—H20120.2
O7A—N6—O5A118.6 (6)C20—C21—C22119.7 (3)
O5B—N6—O6B110.3 (13)C20—C21—H21120.2
O7B—N6—O6B116.7 (14)C22—C21—H21120.2
N1—C1—C2122.5 (2)N4—C22—C21122.6 (3)
N1—C1—H1118.7N4—C22—H22118.7
C2—C1—H1118.7C21—C22—H22118.7
C3—C2—C1120.0 (3)N4—C23—C19122.9 (2)
C3—C2—H2120.0N4—C23—C24117.0 (2)
C1—C2—H2120.0C19—C23—C24120.2 (2)
C2—C3—C4119.2 (2)N3—C24—C16123.7 (2)
C2—C3—H3120.4N3—C24—C23116.5 (2)
C4—C3—H3120.4C16—C24—C23119.8 (2)
C12—C4—C3117.3 (2)O4—C25—O3124.0 (3)
C12—C4—C5118.7 (2)O4—C25—C26123.0 (3)
C3—C4—C5124.0 (2)O3—C25—C26113.0 (3)
C6—C5—C4121.1 (3)C31—C26—C27119.1 (3)
C6—C5—H5119.4C31—C26—C25118.7 (3)
C4—C5—H5119.4C27—C26—C25122.2 (3)
C5—C6—C7121.2 (2)C28—C27—C26120.5 (3)
C5—C6—H6119.4C28—C27—H27119.8
C7—C6—H6119.4C26—C27—H27119.8
C11—C7—C8116.4 (2)C29—C28—C27118.6 (3)
C11—C7—C6119.1 (2)C29—C28—H28120.7
C8—C7—C6124.5 (2)C27—C28—H28120.7
C9—C8—C7119.8 (2)C30—C29—C28121.8 (3)
C9—C8—H8120.1C30—C29—N5119.3 (3)
C7—C8—H8120.1C28—C29—N5118.8 (3)
C8—C9—C10119.9 (3)C31—C30—C29118.9 (3)
C8—C9—H9120.1C31—C30—H30120.6
C10—C9—H9120.1C29—C30—H30120.6
N2—C10—C9122.5 (3)C30—C31—C26121.1 (3)
N2—C10—H10118.8C30—C31—H31119.5
C9—C10—H10118.8C26—C31—H31119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1W0.831.742.566 (3)170
O1W—H1A···O5A0.891.852.73 (1)172
O1W—H1A···O5B0.891.962.84 (3)171
O1W—H1B···Cl0.842.313.146 (2)176
 

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