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The title compound, [NiCl(C12H8N2)2(H2O)]Cl·C7H6O3·2H2O, is composed of NiII complex cations, uncoord­inated chloride anions, 4-hydroxy­benzoic acid (HBA) and uncoordinated water mol­ecules. The NiII atom is surrounded by two phenanthroline (phen) mol­ecules, a chloride anion and a water mol­ecule in a distorted octa­hedral geometry. π–π stacking occurs between parallel phen ligands and between the nearly parallel carbox­yl groups of HBA and the phen ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024098/ng6173sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024098/ng6173Isup2.hkl
Contains datablock I

CCDC reference: 283964

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C)= 0.005 Å
  • R factor = 0.041
  • wR factor = 0.145
  • Data-to-parameter ratio = 17.0

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: 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 for Windows (Farrugia, 1997) and XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

cis-Aquachlorobis(1,10-phenanthroline)nickel(II) chloride 4-hydroxybenzoic acid dihydrate top
Crystal data top
[NiCl(C12H8N2)2(H2O)]Cl·C7H6O3·2H2OZ = 2
Mr = 682.18F(000) = 704
Triclinic, P1Dx = 1.529 Mg m3
Dm = 1.528 Mg m3
Dm measured by flotation in a cyclohexane/CCl4 mixture
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.670 (5) ÅCell parameters from 12708 reflections
b = 12.553 (5) Åθ = 3.0–26.6°
c = 13.505 (5) ŵ = 0.89 mm1
α = 115.242 (12)°T = 295 K
β = 93.281 (17)°Block, green
γ = 110.841 (17)°0.35 × 0.30 × 0.19 mm
V = 1481.7 (11) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6737 independent reflections
Radiation source: fine-focus sealed tube5197 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1313
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1615
Tmin = 0.736, Tmax = 0.849l = 1617
14658 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) = 0.145H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0988P)2]
6737 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.52 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
Ni0.83467 (3)0.47665 (3)0.80539 (2)0.02725 (12)
Cl11.02406 (7)0.41297 (7)0.80652 (6)0.03780 (17)
Cl20.75529 (9)0.96968 (8)0.96860 (8)0.0561 (2)
O1W0.9531 (3)0.8686 (2)1.0565 (2)0.0559 (6)
H1B1.03530.91501.05920.080*
H1A0.89870.89721.02640.080*
O2W0.4034 (4)0.8632 (3)0.8775 (3)0.0965 (11)
H2A0.46990.89140.93820.080*
H2B0.32810.87790.91220.080*
O10.9329 (2)0.62137 (19)0.97217 (16)0.0417 (5)
H1C0.93550.69701.00360.080*
H1D0.95440.61421.03180.080*
O310.4620 (2)0.4128 (2)0.57469 (18)0.0503 (6)
H310.51820.47520.57300.080*
O320.3835 (3)0.3516 (2)0.39432 (18)0.0540 (6)
O330.0620 (3)0.1639 (2)0.4232 (2)0.0598 (7)
H330.02880.22660.35510.080*
N10.6665 (2)0.5264 (2)0.82498 (17)0.0292 (4)
N20.7083 (2)0.3379 (2)0.84595 (19)0.0327 (5)
N30.7450 (2)0.3492 (2)0.63166 (18)0.0320 (5)
N40.9249 (2)0.5985 (2)0.73898 (18)0.0307 (5)
C10.6504 (3)0.6253 (3)0.8221 (2)0.0376 (6)
H10.72350.68570.81330.045*
C20.5285 (3)0.6425 (3)0.8317 (3)0.0440 (7)
H20.52110.71280.82890.053*
C30.4203 (3)0.5550 (3)0.8454 (2)0.0450 (7)
H30.33840.56510.85150.054*
C40.4337 (3)0.4499 (3)0.8502 (2)0.0380 (6)
C50.3260 (3)0.3528 (3)0.8627 (3)0.0478 (7)
H50.24140.35760.86800.057*
C60.3449 (3)0.2541 (3)0.8671 (3)0.0470 (7)
H60.27280.19150.87450.056*
C70.4734 (3)0.2441 (3)0.8608 (2)0.0394 (6)
C80.5004 (4)0.1456 (3)0.8673 (3)0.0503 (8)
H80.43130.08010.87370.060*
C90.6264 (4)0.1457 (3)0.8642 (3)0.0526 (8)
H90.64440.08010.86800.063*
C100.7291 (3)0.2446 (3)0.8553 (3)0.0442 (7)
H100.81650.24520.85600.053*
C110.5814 (3)0.3391 (2)0.8498 (2)0.0315 (5)
C120.5601 (3)0.4414 (2)0.8408 (2)0.0308 (5)
C130.6594 (3)0.2239 (3)0.5792 (2)0.0429 (7)
H130.63640.18110.62170.051*
C140.6025 (4)0.1540 (3)0.4626 (3)0.0517 (8)
H140.54190.06660.42880.062*
C150.6362 (3)0.2141 (3)0.3988 (3)0.0489 (8)
H150.59910.16810.32110.059*
C160.7271 (3)0.3456 (3)0.4506 (2)0.0379 (6)
C170.7683 (4)0.4173 (3)0.3907 (2)0.0475 (8)
H170.73350.37550.31280.057*
C180.8560 (4)0.5437 (3)0.4441 (3)0.0479 (7)
H180.88050.58820.40310.057*
C190.9123 (3)0.6107 (3)0.5646 (2)0.0377 (6)
C201.0067 (4)0.7427 (3)0.6250 (3)0.0469 (7)
H201.03330.79190.58820.056*
C211.0579 (4)0.7964 (3)0.7377 (3)0.0493 (8)
H211.12040.88320.77860.059*
C221.0169 (3)0.7214 (3)0.7928 (2)0.0423 (7)
H221.05560.75930.86970.051*
C230.8743 (3)0.5435 (2)0.6259 (2)0.0303 (5)
C240.7789 (3)0.4094 (3)0.5683 (2)0.0303 (5)
C310.3850 (3)0.3284 (3)0.4757 (2)0.0368 (6)
C320.2967 (3)0.1990 (3)0.4608 (2)0.0374 (6)
C330.2180 (3)0.0976 (3)0.3534 (2)0.0433 (7)
H320.22030.11180.29120.052*
C340.1372 (4)0.0236 (3)0.3398 (3)0.0473 (7)
H340.08270.09050.26880.057*
C350.1370 (4)0.0457 (3)0.4316 (3)0.0453 (7)
C360.2131 (4)0.0542 (3)0.5379 (3)0.0559 (9)
H360.21150.03950.59980.067*
C370.2915 (4)0.1757 (3)0.5517 (3)0.0480 (8)
H370.34180.24320.62370.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.02489 (19)0.03104 (19)0.02790 (18)0.00966 (13)0.00698 (12)0.01750 (14)
Cl10.0316 (3)0.0485 (4)0.0418 (3)0.0199 (3)0.0105 (3)0.0262 (3)
Cl20.0501 (5)0.0432 (4)0.0678 (5)0.0147 (3)0.0066 (4)0.0254 (4)
O1W0.0625 (16)0.0477 (12)0.0679 (15)0.0242 (11)0.0242 (12)0.0346 (12)
O2W0.112 (3)0.108 (3)0.0706 (19)0.062 (2)0.0114 (19)0.0328 (19)
O10.0515 (13)0.0407 (10)0.0289 (9)0.0174 (9)0.0049 (8)0.0155 (8)
O310.0574 (14)0.0389 (11)0.0396 (10)0.0078 (10)0.0012 (10)0.0175 (9)
O320.0616 (15)0.0457 (12)0.0451 (12)0.0084 (11)0.0032 (11)0.0262 (10)
O330.0806 (19)0.0401 (12)0.0520 (13)0.0117 (11)0.0179 (12)0.0273 (11)
N10.0293 (11)0.0327 (10)0.0269 (10)0.0121 (9)0.0054 (8)0.0164 (9)
N20.0298 (12)0.0356 (11)0.0377 (11)0.0132 (9)0.0099 (9)0.0220 (10)
N30.0294 (11)0.0346 (11)0.0308 (10)0.0112 (9)0.0058 (8)0.0167 (9)
N40.0306 (11)0.0331 (11)0.0320 (10)0.0113 (9)0.0112 (9)0.0200 (9)
C10.0364 (15)0.0382 (14)0.0378 (13)0.0139 (11)0.0043 (11)0.0199 (12)
C20.0489 (18)0.0396 (15)0.0445 (15)0.0269 (14)0.0063 (13)0.0150 (13)
C30.0418 (17)0.0538 (17)0.0408 (15)0.0288 (14)0.0105 (13)0.0168 (14)
C40.0301 (14)0.0522 (16)0.0297 (12)0.0194 (12)0.0070 (10)0.0164 (12)
C50.0306 (15)0.064 (2)0.0489 (16)0.0185 (14)0.0171 (13)0.0278 (16)
C60.0336 (16)0.0580 (18)0.0512 (17)0.0120 (14)0.0194 (13)0.0324 (16)
C70.0362 (15)0.0439 (15)0.0382 (14)0.0104 (12)0.0115 (12)0.0247 (12)
C80.0477 (19)0.0470 (17)0.0639 (19)0.0114 (14)0.0190 (15)0.0394 (16)
C90.057 (2)0.0543 (18)0.072 (2)0.0269 (16)0.0244 (17)0.0473 (18)
C100.0398 (17)0.0485 (16)0.0617 (19)0.0232 (13)0.0183 (14)0.0368 (15)
C110.0300 (13)0.0361 (13)0.0266 (11)0.0101 (11)0.0091 (10)0.0163 (11)
C120.0308 (13)0.0346 (13)0.0258 (11)0.0142 (10)0.0085 (10)0.0130 (10)
C130.0434 (17)0.0378 (14)0.0412 (15)0.0109 (13)0.0068 (13)0.0191 (13)
C140.0460 (19)0.0389 (15)0.0440 (16)0.0062 (13)0.0022 (14)0.0082 (14)
C150.0445 (18)0.0513 (18)0.0326 (13)0.0167 (14)0.0027 (12)0.0083 (13)
C160.0354 (15)0.0514 (16)0.0301 (12)0.0228 (13)0.0075 (11)0.0185 (12)
C170.0503 (19)0.071 (2)0.0300 (13)0.0310 (17)0.0103 (12)0.0266 (15)
C180.056 (2)0.070 (2)0.0442 (15)0.0349 (17)0.0223 (14)0.0427 (16)
C190.0381 (16)0.0497 (16)0.0404 (14)0.0231 (13)0.0160 (12)0.0298 (13)
C200.054 (2)0.0500 (17)0.0576 (18)0.0227 (15)0.0251 (15)0.0415 (15)
C210.053 (2)0.0377 (15)0.0534 (18)0.0095 (13)0.0205 (15)0.0255 (14)
C220.0408 (16)0.0364 (14)0.0387 (14)0.0068 (12)0.0110 (12)0.0161 (12)
C230.0297 (13)0.0369 (13)0.0328 (12)0.0188 (11)0.0132 (10)0.0192 (11)
C240.0271 (13)0.0386 (13)0.0304 (12)0.0161 (10)0.0089 (10)0.0188 (11)
C310.0351 (15)0.0384 (14)0.0385 (14)0.0174 (12)0.0089 (11)0.0181 (12)
C320.0372 (15)0.0371 (14)0.0366 (13)0.0156 (12)0.0083 (11)0.0167 (12)
C330.0534 (19)0.0400 (15)0.0334 (13)0.0170 (13)0.0059 (13)0.0176 (12)
C340.054 (2)0.0374 (15)0.0384 (14)0.0141 (14)0.0045 (13)0.0131 (13)
C350.0534 (19)0.0374 (14)0.0441 (15)0.0157 (13)0.0163 (14)0.0207 (13)
C360.077 (3)0.0488 (17)0.0387 (15)0.0175 (17)0.0160 (16)0.0256 (14)
C370.060 (2)0.0399 (15)0.0356 (14)0.0163 (14)0.0094 (14)0.0146 (13)
Geometric parameters (Å, º) top
Ni—O12.087 (2)C7—C111.402 (4)
Ni—N12.095 (2)C8—C91.347 (5)
Ni—N22.092 (2)C8—H80.9300
Ni—N32.105 (2)C9—C101.390 (4)
Ni—N42.072 (2)C9—H90.9300
Ni—Cl12.4246 (12)C10—H100.9300
O1W—H1B0.8520C11—C121.433 (4)
O1W—H1A0.9374C13—C141.398 (4)
O2W—H2A0.8988C13—H130.9300
O2W—H2B0.9867C14—C151.354 (5)
O1—H1C0.8476C14—H140.9300
O1—H1D0.8739C15—C161.398 (4)
O31—C311.278 (4)C15—H150.9300
O31—H310.8101C16—C241.405 (4)
O32—C311.252 (4)C16—C171.427 (5)
O33—C351.362 (4)C17—C181.343 (5)
O33—H330.8592C17—H170.9300
N1—C11.328 (3)C18—C191.442 (4)
N1—C121.353 (3)C18—H180.9300
N2—C101.321 (4)C19—C231.398 (4)
N2—C111.363 (4)C19—C201.410 (4)
N3—C131.327 (4)C20—C211.355 (5)
N3—C241.352 (3)C20—H200.9300
N4—C221.325 (3)C21—C221.405 (4)
N4—C231.357 (3)C21—H210.9300
C1—C21.396 (4)C22—H220.9300
C1—H10.9300C23—C241.431 (4)
C2—C31.367 (5)C31—C321.476 (4)
C2—H20.9300C32—C371.378 (4)
C3—C41.404 (4)C32—C331.399 (4)
C3—H30.9300C33—C341.380 (4)
C4—C121.399 (4)C33—H320.9300
C4—C51.428 (4)C34—C351.381 (5)
C5—C61.348 (5)C34—H340.9300
C5—H50.9300C35—C361.377 (5)
C6—C71.425 (5)C36—C371.375 (5)
C6—H60.9300C36—H360.9300
C7—C81.401 (4)C37—H370.9300
O1—Ni—N187.56 (9)N2—C11—C7122.4 (3)
O1—Ni—N295.69 (9)N2—C11—C12117.5 (2)
O1—Ni—N3172.87 (8)C7—C11—C12120.1 (2)
O1—Ni—N493.57 (9)N1—C12—C4123.6 (3)
O1—Ni—Cl187.88 (7)N1—C12—C11117.1 (2)
N1—Ni—N279.59 (9)C4—C12—C11119.3 (3)
N1—Ni—N391.72 (9)N3—C13—C14122.5 (3)
N1—Ni—N493.79 (9)N3—C13—H13118.8
N1—Ni—Cl1171.40 (6)C14—C13—H13118.8
N2—Ni—N391.15 (9)C15—C14—C13119.7 (3)
N2—Ni—N4168.35 (9)C15—C14—H14120.1
N2—Ni—Cl193.62 (7)C13—C14—H14120.1
N3—Ni—N479.39 (9)C14—C15—C16119.6 (3)
N3—Ni—Cl193.71 (7)C14—C15—H15120.2
N4—Ni—Cl193.77 (7)C16—C15—H15120.2
H1B—O1W—H1A103.6C15—C16—C24117.3 (3)
H2A—O2W—H2B101.9C15—C16—C17123.7 (3)
Ni—O1—H1C127.1C24—C16—C17119.0 (3)
Ni—O1—H1D129.5C18—C17—C16121.6 (3)
H1C—O1—H1D100.2C18—C17—H17119.2
C31—O31—H31110.1C16—C17—H17119.2
C35—O33—H33114.2C17—C18—C19120.4 (3)
C1—N1—C12117.6 (2)C17—C18—H18119.8
C1—N1—Ni129.58 (19)C19—C18—H18119.8
C12—N1—Ni112.85 (17)C23—C19—C20117.5 (3)
C10—N2—C11117.9 (2)C23—C19—C18119.5 (3)
C10—N2—Ni129.4 (2)C20—C19—C18123.0 (3)
C11—N2—Ni112.22 (18)C21—C20—C19118.9 (3)
C13—N3—C24117.9 (2)C21—C20—H20120.6
C13—N3—Ni129.5 (2)C19—C20—H20120.6
C24—N3—Ni112.51 (17)C20—C21—C22120.2 (3)
C22—N4—C23117.9 (2)C20—C21—H21119.9
C22—N4—Ni128.70 (19)C22—C21—H21119.9
C23—N4—Ni113.28 (17)N4—C22—C21122.2 (3)
N1—C1—C2122.9 (3)N4—C22—H22118.9
N1—C1—H1118.5C21—C22—H22118.9
C2—C1—H1118.5N4—C23—C19123.2 (2)
C3—C2—C1119.3 (3)N4—C23—C24117.3 (2)
C3—C2—H2120.3C19—C23—C24119.5 (2)
C1—C2—H2120.3N3—C24—C16123.0 (3)
C2—C3—C4119.5 (3)N3—C24—C23117.1 (2)
C2—C3—H3120.2C16—C24—C23119.9 (3)
C4—C3—H3120.2O32—C31—O31123.0 (3)
C12—C4—C3117.0 (3)O32—C31—C32120.8 (3)
C12—C4—C5119.4 (3)O31—C31—C32116.2 (3)
C3—C4—C5123.6 (3)C37—C32—C33119.0 (3)
C6—C5—C4121.0 (3)C37—C32—C31120.8 (3)
C6—C5—H5119.5C33—C32—C31120.1 (3)
C4—C5—H5119.5C34—C33—C32119.8 (3)
C5—C6—C7121.2 (3)C34—C33—H32120.1
C5—C6—H6119.4C32—C33—H32120.1
C7—C6—H6119.4C33—C34—C35120.1 (3)
C8—C7—C11117.2 (3)C33—C34—H34120.0
C8—C7—C6123.9 (3)C35—C34—H34120.0
C11—C7—C6118.9 (3)O33—C35—C36116.9 (3)
C9—C8—C7120.1 (3)O33—C35—C34122.8 (3)
C9—C8—H8119.9C36—C35—C34120.3 (3)
C7—C8—H8119.9C37—C36—C35119.6 (3)
C8—C9—C10119.4 (3)C37—C36—H36120.2
C8—C9—H9120.3C35—C36—H36120.2
C10—C9—H9120.3C36—C37—C32121.1 (3)
N2—C10—C9123.1 (3)C36—C37—H37119.4
N2—C10—H10118.5C32—C37—H37119.4
C9—C10—H10118.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···Cl20.942.293.221 (4)174
O1W—H1B···Cl2i0.852.343.183 (4)169
O2W—H2A···Cl20.902.793.449 (5)131
O2W—H2B···Cl2ii0.992.413.286 (5)148
O1—H1C···O1W0.851.892.731 (4)171
O1—H1D···Cl1iii0.872.363.227 (3)171
O31—H31···O32iv0.811.882.652 (4)160
O33—H33···Cl1v0.862.263.099 (3)164
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+2, z+2; (iii) x+2, y+1, z+2; (iv) x+1, y+1, z+1; (v) x+1, y, z+1.
 

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