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In the title com­pound, {[Co(C9H6O4)(H2O)]·0.5C16H20N4·0.5H2O}n, two-di­men­sional coordination polymer slabs are held together in the three-dimensional crystal structure by means of O—H...N hydrogen bonding between bound water mol­ecules and pyridyl N atoms of cocrystallized 1,4-bis­(pyridin-4-yl­meth­yl)piperazine mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462300648X/bt4140sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431462300648X/bt4140Isup2.hkl
Contains datablock I

CCDC reference: 1946425

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.041
  • wR factor = 0.113
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Bond Without Acceptor O1W --H1WB . Please Check
Alert level C PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ Please Check PLAT260_ALERT_2_C Large Average Ueq of Residue Including O1W 0.131 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 35 Report PLAT975_ALERT_2_C Check Calcd Resid. Dens. 0.93Ang From O4 . 0.40 eA-3 PLAT976_ALERT_2_C Check Calcd Resid. Dens. 0.56Ang From O1W . -0.64 eA-3 PLAT976_ALERT_2_C Check Calcd Resid. Dens. 0.59Ang From O1W . -0.49 eA-3
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 5 Note PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension 2 Info PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 5.85 Why ? PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 3 Report PLAT300_ALERT_4_G Atom Site Occupancy of O1W Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H1WA Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H1WB Constrained at 0.5 Check PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 3 ) 100% Note PLAT415_ALERT_2_G Short Inter D-H..H-X H1WA ..H17B . 2.03 Ang. x,y,z = 1_555 Check PLAT415_ALERT_2_G Short Inter D-H..H-X H1WA ..H16B . 2.13 Ang. 1-x,1-y,2-z = 5_667 Check PLAT415_ALERT_2_G Short Inter D-H..H-X H1WB ..H15B . 2.12 Ang. x,1+y,z = 1_565 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT794_ALERT_5_G Tentative Bond Valency for Co1 (II) . 2.03 Info PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 6 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 3 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 2.8 Low PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 20 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[(µ-aqua)[µ4-4-(carboxylatomethyl)benzoato]cobalt(II)] hemi[1,4-bis(pyridin-4-ylmethyl)piperazine] hemihydrate] top
Crystal data top
[Co(C9H6O4)(H2O)]·0.5C16H20N4·0.5H2OF(000) = 1648
Mr = 796.54Dx = 1.559 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.036 (6) ÅCell parameters from 3416 reflections
b = 6.3093 (13) Åθ = 2.1–25.4°
c = 20.653 (5) ŵ = 1.05 mm1
β = 105.536 (6)°T = 173 K
V = 3394.2 (13) Å3Block, pink
Z = 40.27 × 0.14 × 0.09 mm
Data collection top
Bruker APEXII CCD
diffractometer
3089 independent reflections
Radiation source: sealed tube2334 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.36 pixels mm-1θmax = 25.4°, θmin = 2.1°
ω scansh = 3132
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 77
Tmin = 0.669, Tmax = 0.745l = 2424
8691 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0475P)2 + 5.8489P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
3089 reflectionsΔρmax = 0.65 e Å3
243 parametersΔρmin = 0.66 e Å3
3 restraints
Special details top

Experimental. Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using omega scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structure was solved by the direct method using the SHELXT program and refined by least squares method on F2, SHELXL, incorporated in OLEX2.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structure was refined by Least Squares using version 2018/3 of XL (Sheldrick, 2015) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Co10.74834 (2)0.12245 (6)0.74217 (2)0.01613 (16)
O10.77518 (9)0.2010 (3)0.66350 (10)0.0218 (5)
O20.77731 (9)0.5545 (3)0.67641 (10)0.0214 (5)
O30.84413 (9)0.8638 (3)0.37647 (11)0.0251 (6)
O40.79387 (8)0.6398 (3)0.30472 (10)0.0177 (5)
O50.69426 (9)0.3776 (3)0.72357 (11)0.0176 (5)
N10.61639 (12)0.3261 (5)0.77903 (15)0.0320 (7)
N20.50168 (11)0.4195 (5)0.93570 (14)0.0300 (7)
C10.78312 (12)0.3868 (5)0.64604 (14)0.0174 (7)
C20.80076 (12)0.4150 (5)0.58368 (15)0.0200 (7)
C30.80611 (13)0.6162 (5)0.56001 (16)0.0222 (7)
H30.7990690.7362330.5838580.027*
C40.82169 (14)0.6449 (5)0.50162 (16)0.0272 (8)
H40.8246410.7842290.4856010.033*
C50.83291 (12)0.4727 (5)0.46672 (14)0.0185 (7)
C60.82768 (13)0.2713 (5)0.49056 (16)0.0255 (8)
H60.8351910.1516540.4669030.031*
C70.81175 (13)0.2408 (5)0.54812 (16)0.0251 (8)
H70.8082680.1011570.5635450.030*
C80.85144 (13)0.4970 (5)0.40366 (14)0.0202 (7)
H8A0.8892290.5138290.4172830.024*
H8B0.8435140.3649300.3770150.024*
C90.82837 (13)0.6809 (5)0.35940 (15)0.0195 (7)
C100.60190 (15)0.4890 (7)0.81086 (19)0.0395 (10)
H100.6173590.6233220.8090650.047*
C110.56540 (16)0.4711 (6)0.8464 (2)0.0419 (10)
H110.5560360.5916210.8679830.050*
C120.54265 (14)0.2779 (6)0.85029 (17)0.0304 (8)
C130.55802 (15)0.1093 (6)0.81812 (19)0.0355 (9)
H130.5435380.0271440.8197870.043*
C140.59459 (15)0.1393 (6)0.78341 (19)0.0354 (9)
H140.6046980.0208410.7615800.043*
C150.50169 (15)0.2492 (7)0.88805 (19)0.0373 (10)
H15A0.4675250.2425470.8551630.045*
H15B0.5075360.1126210.9125250.045*
C160.54563 (14)0.4017 (6)0.99510 (18)0.0345 (9)
H16A0.5779290.4030100.9811730.041*
H16B0.5437480.2659311.0183440.041*
C170.45449 (14)0.4153 (7)0.95746 (19)0.0371 (10)
H17A0.4521010.2795720.9804610.045*
H17B0.4243690.4263460.9178540.045*
O1W0.4535 (4)0.7370 (16)0.8420 (5)0.131 (4)0.5
H1WA0.4559060.6727930.8799810.196*0.5
H1WB0.4687360.8580730.8533310.196*0.5
H5A0.6813 (14)0.440 (6)0.6864 (13)0.044 (12)*
H5B0.6705 (14)0.359 (7)0.743 (2)0.072 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0225 (3)0.0114 (2)0.0161 (2)0.00011 (18)0.00797 (18)0.00042 (16)
O10.0344 (15)0.0149 (12)0.0194 (11)0.0002 (10)0.0130 (10)0.0009 (9)
O20.0313 (14)0.0169 (12)0.0196 (11)0.0004 (10)0.0132 (10)0.0000 (9)
O30.0346 (15)0.0200 (13)0.0178 (11)0.0065 (11)0.0019 (10)0.0005 (9)
O40.0228 (13)0.0150 (12)0.0127 (10)0.0003 (9)0.0003 (9)0.0008 (8)
O50.0221 (13)0.0143 (12)0.0168 (11)0.0021 (10)0.0061 (10)0.0019 (9)
N10.0281 (19)0.0404 (19)0.0293 (16)0.0012 (15)0.0109 (14)0.0035 (14)
N20.0225 (17)0.0423 (19)0.0271 (15)0.0019 (14)0.0101 (13)0.0023 (13)
C10.0181 (18)0.0184 (17)0.0152 (15)0.0010 (14)0.0037 (13)0.0017 (13)
C20.0214 (19)0.0233 (18)0.0160 (15)0.0024 (14)0.0059 (13)0.0013 (13)
C30.034 (2)0.0137 (16)0.0223 (16)0.0006 (15)0.0127 (15)0.0021 (13)
C40.045 (2)0.0169 (18)0.0232 (17)0.0018 (16)0.0160 (16)0.0033 (14)
C50.0194 (18)0.0206 (17)0.0148 (14)0.0006 (14)0.0034 (13)0.0001 (13)
C60.036 (2)0.0184 (18)0.0257 (17)0.0017 (16)0.0138 (16)0.0015 (14)
C70.037 (2)0.0154 (17)0.0270 (17)0.0014 (16)0.0160 (16)0.0031 (14)
C80.0246 (19)0.0197 (17)0.0171 (15)0.0014 (15)0.0069 (14)0.0028 (13)
C90.0214 (19)0.0230 (18)0.0172 (15)0.0015 (14)0.0104 (14)0.0021 (13)
C100.046 (3)0.035 (2)0.043 (2)0.004 (2)0.022 (2)0.0025 (19)
C110.053 (3)0.034 (2)0.050 (2)0.002 (2)0.032 (2)0.006 (2)
C120.028 (2)0.035 (2)0.0288 (18)0.0014 (18)0.0088 (16)0.0007 (16)
C130.038 (2)0.030 (2)0.042 (2)0.0035 (18)0.0172 (18)0.0008 (17)
C140.040 (2)0.034 (2)0.036 (2)0.0052 (19)0.0168 (18)0.0008 (17)
C150.036 (2)0.043 (2)0.037 (2)0.005 (2)0.0162 (18)0.0036 (18)
C160.022 (2)0.050 (3)0.033 (2)0.0060 (18)0.0099 (16)0.0004 (18)
C170.020 (2)0.061 (3)0.0313 (19)0.0041 (19)0.0076 (16)0.0082 (18)
O1W0.165 (10)0.120 (8)0.115 (8)0.008 (8)0.052 (7)0.013 (7)
Geometric parameters (Å, º) top
Co1—O12.011 (2)C5—C81.523 (4)
Co1—O2i2.029 (2)C6—H60.9500
Co1—O4ii2.094 (2)C6—C71.382 (4)
Co1—O4iii2.140 (2)C7—H70.9500
Co1—O52.139 (2)C8—H8A0.9900
Co1—O5i2.169 (2)C8—H8B0.9900
O1—C11.262 (4)C8—C91.505 (4)
O2—C11.261 (4)C10—H100.9500
O3—C91.248 (4)C10—C111.383 (5)
O4—C91.284 (4)C11—H110.9500
O5—H5A0.851 (19)C11—C121.377 (5)
O5—H5B0.855 (19)C12—C131.376 (5)
N1—C101.334 (5)C12—C151.526 (5)
N1—C141.332 (5)C13—H130.9500
N2—C151.457 (5)C13—C141.381 (5)
N2—C161.466 (5)C14—H140.9500
N2—C171.462 (4)C15—H15A0.9900
C1—C21.499 (4)C15—H15B0.9900
C2—C31.382 (4)C16—H16A0.9900
C2—C71.397 (4)C16—H16B0.9900
C3—H30.9500C16—C17iv1.515 (5)
C3—C41.392 (4)C17—H17A0.9900
C4—H40.9500C17—H17B0.9900
C4—C51.382 (4)O1W—H1WA0.8698
C5—C61.384 (5)O1W—H1WB0.8699
O1—Co1—O2i177.55 (9)C7—C6—H6119.4
O1—Co1—O4iii92.37 (9)C2—C7—H7119.9
O1—Co1—O4ii95.23 (9)C6—C7—C2120.1 (3)
O1—Co1—O5i93.31 (9)C6—C7—H7119.9
O1—Co1—O592.67 (9)C5—C8—H8A108.6
O2i—Co1—O4iii85.22 (9)C5—C8—H8B108.6
O2i—Co1—O4ii87.21 (9)H8A—C8—H8B107.5
O2i—Co1—O586.49 (9)C9—C8—C5114.8 (3)
O2i—Co1—O5i87.29 (9)C9—C8—H8A108.6
O4ii—Co1—O4iii170.65 (6)C9—C8—H8B108.6
O4iii—Co1—O5i93.25 (8)O3—C9—O4123.2 (3)
O4ii—Co1—O5i80.90 (9)O3—C9—C8119.1 (3)
O4ii—Co1—O5104.48 (9)O4—C9—C8117.7 (3)
O5—Co1—O4iii80.55 (9)N1—C10—H10118.5
O5—Co1—O5i171.56 (4)N1—C10—C11122.9 (4)
C1—O1—Co1125.86 (19)C11—C10—H10118.5
C1—O2—Co1v134.8 (2)C10—C11—H11120.1
Co1ii—O4—Co1vi96.93 (8)C12—C11—C10119.8 (4)
C9—O4—Co1ii138.0 (2)C12—C11—H11120.1
C9—O4—Co1vi123.7 (2)C11—C12—C15122.1 (3)
Co1—O5—Co1v94.73 (9)C13—C12—C11117.3 (3)
Co1—O5—H5A127 (3)C13—C12—C15120.6 (3)
Co1v—O5—H5A93 (3)C12—C13—H13120.2
Co1v—O5—H5B120 (3)C12—C13—C14119.7 (4)
Co1—O5—H5B112 (3)C14—C13—H13120.2
H5A—O5—H5B108 (4)N1—C14—C13123.2 (4)
C14—N1—C10117.0 (3)N1—C14—H14118.4
C15—N2—C16111.2 (3)C13—C14—H14118.4
C15—N2—C17110.6 (3)N2—C15—C12112.9 (3)
C17—N2—C16108.7 (3)N2—C15—H15A109.0
O1—C1—C2118.3 (3)N2—C15—H15B109.0
O2—C1—O1125.7 (3)C12—C15—H15A109.0
O2—C1—C2116.0 (3)C12—C15—H15B109.0
C3—C2—C1120.0 (3)H15A—C15—H15B107.8
C3—C2—C7118.7 (3)N2—C16—H16A109.7
C7—C2—C1121.3 (3)N2—C16—H16B109.7
C2—C3—H3119.6N2—C16—C17iv110.0 (3)
C2—C3—C4120.7 (3)H16A—C16—H16B108.2
C4—C3—H3119.6C17iv—C16—H16A109.7
C3—C4—H4119.7C17iv—C16—H16B109.7
C5—C4—C3120.6 (3)N2—C17—C16iv109.8 (3)
C5—C4—H4119.7N2—C17—H17A109.7
C4—C5—C6118.6 (3)N2—C17—H17B109.7
C4—C5—C8122.4 (3)C16iv—C17—H17A109.7
C6—C5—C8119.0 (3)C16iv—C17—H17B109.7
C5—C6—H6119.4H17A—C17—H17B108.2
C7—C6—C5121.3 (3)H1WA—O1W—H1WB104.5
Co1—O1—C1—O22.7 (5)C5—C6—C7—C20.3 (5)
Co1—O1—C1—C2176.9 (2)C5—C8—C9—O376.4 (4)
Co1v—O2—C1—O13.5 (5)C5—C8—C9—O4105.1 (3)
Co1v—O2—C1—C2176.2 (2)C6—C5—C8—C9145.6 (3)
Co1vi—O4—C9—O311.0 (4)C7—C2—C3—C40.6 (5)
Co1ii—O4—C9—O3174.2 (2)C8—C5—C6—C7179.0 (3)
Co1vi—O4—C9—C8170.56 (19)C10—N1—C14—C130.8 (6)
Co1ii—O4—C9—C87.3 (4)C10—C11—C12—C130.3 (6)
O1—C1—C2—C3175.1 (3)C10—C11—C12—C15179.3 (4)
O1—C1—C2—C74.5 (5)C11—C12—C13—C140.5 (6)
O2—C1—C2—C34.6 (5)C11—C12—C15—N218.8 (5)
O2—C1—C2—C7175.8 (3)C12—C13—C14—N10.1 (6)
N1—C10—C11—C120.5 (6)C13—C12—C15—N2161.7 (3)
C1—C2—C3—C4179.0 (3)C14—N1—C10—C111.0 (6)
C1—C2—C7—C6179.6 (3)C15—N2—C16—C17iv178.2 (3)
C2—C3—C4—C51.0 (5)C15—N2—C17—C16iv177.9 (3)
C3—C2—C7—C60.1 (5)C15—C12—C13—C14179.1 (4)
C3—C4—C5—C60.8 (5)C16—N2—C15—C1273.7 (4)
C3—C4—C5—C8178.3 (3)C16—N2—C17—C16iv59.7 (4)
C4—C5—C6—C70.2 (5)C17—N2—C15—C12165.4 (3)
C4—C5—C8—C935.2 (5)C17—N2—C16—C17iv59.8 (4)
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x+3/2, y+1/2, z+1; (iii) x, y+1, z+1/2; (iv) x+1, y+1, z+2; (v) x+3/2, y+1/2, z+3/2; (vi) x, y+1, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···N20.952.532.860 (5)101
O1W—H1WA···N20.872.162.847 (10)136
O5—H5A···O3vii0.85 (2)1.79 (2)2.619 (3)164 (4)
O5—H5B···N10.86 (2)1.82 (2)2.672 (4)175 (5)
Symmetry code: (vii) x+3/2, y+3/2, z+1.
 

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