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Employment of the organic 2-(pyridin-4-yl)quinoline-4-carb­oxy­lic acid ligand with extended coordination capabilities leads to the formation of the one-dimensional copper(II) coordination polymer catena-poly[[di­aqua­copper(II)]-bis­[μ-2-(pyridin-4-yl)quinoline-4-carboxyl­ato]-κ2N2:O2O:N], {[Cu(C15H9N2O2)2(H2O)2]·2H2O}n, under hydro­thermal conditions. The ligand, isolated as its hydro­chloride salt, namely, 4-(4-carb­oxy­quinolin-2-yl)pyridinium chloride monohydrate, C15H11N2O2+·Cl·H2O, reveals a pseudosymmetry element (translation a/2) in its crystal structure. The additional pyridyl N atom, in com­parison with the previously reported analogues with an arene ring instead of the pyridyl ring in the present ligand mol­ecule, promotes the formation of a one-dimensional coordination polymer, rather than discrete mol­ecules. This polymer shows photoluminescent properties with bathochromic/hypsochromic shifts of the ligand absorption bands, leading to a single band at 479 nm. The CuII ions are involved in weak anti­ferromagnetic inter­actions within dimeric units, as evidenced by SQUID magnetometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620004593/ef3006sup1.cif
Contains datablocks blue26ok, kk6dc, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004593/ef3006blue26oksup2.hkl
Contains datablock blue26ok

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004593/ef3006kk6dcsup3.hkl
Contains datablock kk6dc

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620004593/ef3006IIsup4.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620004593/ef3006sup5.pdf
Additional figures and tables

CCDC references: 1994495; 1994494

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[diaquacopper(II)]-bis[µ-2-(pyridin-4-yl)quinoline-4-carboxylato]-κ2N2,O;κ2O,N] (blue26ok) top
Crystal data top
[Cu(C15H9N2O2)2(H2O)2]·2H2OZ = 1
Mr = 634.09F(000) = 327
Triclinic, P1Dx = 1.503 Mg m3
a = 8.647 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.819 (3) ÅCell parameters from 3141 reflections
c = 10.125 (2) Åθ = 2.2–25.5°
α = 70.58 (2)°µ = 0.84 mm1
β = 79.61 (3)°T = 100 K
γ = 75.26 (3)°Block, blue/green
V = 700.3 (4) Å30.20 × 0.18 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
2397 reflections with I > 2σ(I)
CCD scansRint = 0.031
Absorption correction: analytical
(CrysAlis PRO; Rigaku OD, 2017)
θmax = 28.8°, θmin = 2.2°
Tmin = 0.867, Tmax = 0.940h = 1011
4791 measured reflectionsk = 1110
3141 independent reflectionsl = 1311
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0448P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3141 reflectionsΔρmax = 0.92 e Å3
196 parametersΔρmin = 0.36 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.5000001.0000000.0000000.01642 (17)
O10.3010 (2)0.9513 (2)0.1250 (2)0.0181 (5)
O20.2854 (3)0.7167 (3)0.0924 (2)0.0321 (6)
O1W0.2261 (3)0.4049 (2)0.1788 (2)0.0315 (6)
H1WA0.2371140.5019350.1663670.047*
H1WB0.1534310.3892670.2476770.047*
O2W0.5056 (2)0.8188 (2)0.1296 (2)0.0231 (5)
H2WA0.4442460.7667550.0646350.035*
H2WB0.5851360.7493250.1521450.035*
N10.0033 (3)0.6870 (3)0.5775 (2)0.0160 (5)
N20.3666 (3)0.1778 (3)0.8565 (2)0.0168 (5)
C10.1575 (3)0.7750 (3)0.3026 (3)0.0155 (6)
C20.0135 (3)0.8792 (3)0.3388 (3)0.0154 (6)
C30.0599 (3)1.0275 (3)0.2441 (3)0.0193 (7)
H30.0125691.0619980.1497080.023*
C40.1986 (4)1.1217 (4)0.2876 (3)0.0223 (7)
H40.2472121.2213360.2233720.027*
C50.2697 (4)1.0718 (4)0.4268 (3)0.0218 (7)
H50.3660161.1386490.4555460.026*
C60.2034 (3)0.9299 (3)0.5214 (3)0.0185 (6)
H60.2533620.8984400.6151210.022*
C70.0592 (3)0.8285 (3)0.4800 (3)0.0155 (6)
C80.1395 (3)0.5940 (3)0.5397 (3)0.0158 (6)
C90.2181 (3)0.6343 (3)0.4019 (3)0.0175 (6)
H90.3138430.5629800.3781520.021*
C100.2543 (3)0.8177 (4)0.1587 (3)0.0183 (7)
C110.2129 (3)0.4456 (3)0.6501 (3)0.0164 (6)
C120.3270 (3)0.3172 (3)0.6151 (3)0.0181 (6)
H120.3542920.3193080.5193980.022*
C130.3997 (3)0.1878 (3)0.7199 (3)0.0179 (6)
H130.4768180.1015580.6941210.022*
C140.2525 (3)0.2975 (3)0.8913 (3)0.0193 (7)
H140.2240360.2893040.9881250.023*
C150.1750 (3)0.4312 (3)0.7933 (3)0.0188 (6)
H150.0959660.5136380.8226710.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0165 (3)0.0143 (3)0.0107 (3)0.0012 (2)0.0006 (2)0.0037 (2)
O10.0182 (11)0.0133 (10)0.0171 (10)0.0033 (9)0.0018 (8)0.0009 (8)
O20.0469 (15)0.0266 (12)0.0241 (12)0.0176 (11)0.0144 (11)0.0112 (11)
O1W0.0348 (14)0.0218 (12)0.0305 (13)0.0074 (10)0.0149 (11)0.0069 (10)
O2W0.0216 (11)0.0222 (11)0.0195 (11)0.0042 (9)0.0032 (9)0.0015 (9)
N10.0161 (13)0.0146 (12)0.0135 (12)0.0017 (10)0.0018 (10)0.0006 (10)
N20.0165 (13)0.0162 (12)0.0123 (12)0.0013 (10)0.0012 (10)0.0005 (10)
C10.0174 (15)0.0165 (15)0.0116 (14)0.0049 (12)0.0016 (12)0.0020 (12)
C20.0155 (15)0.0146 (14)0.0145 (14)0.0047 (12)0.0016 (12)0.0011 (12)
C30.0210 (16)0.0187 (15)0.0146 (14)0.0031 (13)0.0034 (13)0.0004 (12)
C40.0230 (17)0.0168 (15)0.0242 (16)0.0011 (13)0.0091 (14)0.0012 (13)
C50.0172 (16)0.0198 (16)0.0267 (17)0.0006 (13)0.0028 (13)0.0080 (14)
C60.0174 (15)0.0184 (15)0.0171 (15)0.0030 (12)0.0010 (12)0.0042 (12)
C70.0165 (15)0.0139 (14)0.0145 (14)0.0020 (12)0.0014 (12)0.0032 (12)
C80.0189 (15)0.0145 (14)0.0119 (14)0.0064 (12)0.0000 (12)0.0002 (12)
C90.0179 (15)0.0153 (15)0.0152 (14)0.0001 (12)0.0004 (12)0.0025 (12)
C100.0164 (15)0.0184 (16)0.0142 (14)0.0002 (12)0.0025 (12)0.0003 (12)
C110.0181 (15)0.0163 (15)0.0130 (14)0.0049 (12)0.0038 (12)0.0001 (12)
C120.0213 (16)0.0185 (15)0.0107 (14)0.0026 (13)0.0009 (12)0.0022 (12)
C130.0198 (16)0.0161 (15)0.0138 (14)0.0012 (12)0.0006 (12)0.0025 (12)
C140.0222 (16)0.0197 (15)0.0118 (14)0.0028 (13)0.0009 (13)0.0020 (12)
C150.0195 (16)0.0176 (15)0.0145 (14)0.0004 (12)0.0005 (12)0.0027 (12)
Geometric parameters (Å, º) top
Cu1—O11.994 (2)C2—C71.426 (4)
Cu1—O1i1.994 (2)C3—C41.367 (4)
Cu1—N2ii2.017 (2)C3—H30.9500
Cu1—N2iii2.017 (2)C4—C51.403 (4)
Cu1—O2W2.368 (2)C4—H40.9500
Cu1—O2Wi2.368 (2)C5—C61.359 (4)
O1—C101.262 (3)C5—H50.9500
O2—C101.235 (3)C6—C71.422 (4)
O1W—H1WA0.8499C6—H60.9500
O1W—H1WB0.8500C8—C91.410 (4)
O2W—H2WA0.8500C8—C111.492 (4)
O2W—H2WB0.8500C9—H90.9500
N1—C81.327 (4)C11—C151.397 (4)
N1—C71.362 (3)C11—C121.398 (4)
N2—C131.339 (4)C12—C131.376 (4)
N2—C141.344 (4)C12—H120.9500
C1—C91.362 (4)C13—H130.9500
C1—C21.416 (4)C14—C151.372 (4)
C1—C101.524 (4)C14—H140.9500
C2—C31.413 (4)C15—H150.9500
O1—Cu1—O1i180.0C5—C4—H4119.8
O1—Cu1—N2ii89.53 (9)C6—C5—C4121.3 (3)
O1i—Cu1—N2ii90.47 (9)C6—C5—H5119.3
O1—Cu1—N2iii90.47 (9)C4—C5—H5119.3
O1i—Cu1—N2iii89.53 (9)C5—C6—C7120.0 (3)
N2ii—Cu1—N2iii180.0C5—C6—H6120.0
O1—Cu1—O2W95.24 (8)C7—C6—H6120.0
O1i—Cu1—O2W84.76 (8)N1—C7—C6118.3 (2)
N2ii—Cu1—O2W92.18 (9)N1—C7—C2122.9 (3)
N2iii—Cu1—O2W87.82 (9)C6—C7—C2118.8 (2)
O1—Cu1—O2Wi84.76 (8)N1—C8—C9122.3 (2)
O1i—Cu1—O2Wi95.24 (8)N1—C8—C11117.8 (2)
N2ii—Cu1—O2Wi87.82 (9)C9—C8—C11119.8 (3)
N2iii—Cu1—O2Wi92.18 (9)C1—C9—C8120.3 (3)
O2W—Cu1—O2Wi180.0C1—C9—H9119.8
C10—O1—Cu1125.15 (19)C8—C9—H9119.8
H1WA—O1W—H1WB104.1O2—C10—O1127.6 (3)
Cu1—O2W—H2WA91.1O2—C10—C1117.9 (2)
Cu1—O2W—H2WB128.4O1—C10—C1114.5 (3)
H2WA—O2W—H2WB108.3C15—C11—C12116.9 (3)
C8—N1—C7118.3 (2)C15—C11—C8121.5 (3)
C13—N2—C14117.5 (2)C12—C11—C8121.6 (3)
C13—N2—Cu1iv120.14 (19)C13—C12—C11119.7 (3)
C14—N2—Cu1iv122.07 (19)C13—C12—H12120.2
C9—C1—C2119.3 (3)C11—C12—H12120.2
C9—C1—C10117.8 (3)N2—C13—C12123.0 (3)
C2—C1—C10122.9 (2)N2—C13—H13118.5
C3—C2—C1123.9 (3)C12—C13—H13118.5
C3—C2—C7119.2 (3)N2—C14—C15123.0 (3)
C1—C2—C7116.8 (2)N2—C14—H14118.5
C4—C3—C2120.3 (3)C15—C14—H14118.5
C4—C3—H3119.8C14—C15—C11119.8 (3)
C2—C3—H3119.8C14—C15—H15120.1
C3—C4—C5120.3 (3)C11—C15—H15120.1
C3—C4—H4119.8
C9—C1—C2—C3179.9 (3)C11—C8—C9—C1175.9 (2)
C10—C1—C2—C33.8 (4)Cu1—O1—C10—O225.3 (4)
C9—C1—C2—C70.2 (4)Cu1—O1—C10—C1150.54 (18)
C10—C1—C2—C7176.2 (3)C9—C1—C10—O258.0 (4)
C1—C2—C3—C4179.7 (3)C2—C1—C10—O2125.6 (3)
C7—C2—C3—C40.3 (4)C9—C1—C10—O1118.3 (3)
C2—C3—C4—C50.1 (5)C2—C1—C10—O158.1 (4)
C3—C4—C5—C60.1 (5)N1—C8—C11—C1520.8 (4)
C4—C5—C6—C70.0 (4)C9—C8—C11—C15156.9 (3)
C8—N1—C7—C6178.7 (3)N1—C8—C11—C12161.5 (3)
C8—N1—C7—C21.3 (4)C9—C8—C11—C1220.7 (4)
C5—C6—C7—N1179.8 (3)C15—C11—C12—C132.1 (4)
C5—C6—C7—C20.3 (4)C8—C11—C12—C13175.6 (2)
C3—C2—C7—N1179.6 (3)C14—N2—C13—C122.7 (4)
C1—C2—C7—N10.4 (4)Cu1iv—N2—C13—C12171.7 (2)
C3—C2—C7—C60.4 (4)C11—C12—C13—N20.1 (4)
C1—C2—C7—C6179.6 (3)C13—N2—C14—C153.0 (4)
C7—N1—C8—C91.9 (4)Cu1iv—N2—C14—C15171.2 (2)
C7—N1—C8—C11175.7 (2)N2—C14—C15—C110.8 (5)
C2—C1—C9—C80.8 (4)C12—C11—C15—C141.8 (4)
C10—C1—C9—C8175.7 (3)C8—C11—C15—C14176.0 (3)
N1—C8—C9—C11.8 (4)
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1, z+1; (iii) x, y+1, z1; (iv) x, y1, z+1.
4-(4-Carboxyquinolin-2-yl)pyridinium chloride monohydrate (kk6dc) top
Crystal data top
C15H11N2O2+·Cl·H2OF(000) = 1264
Mr = 304.72Dx = 1.496 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.402 (3) ÅCell parameters from 5674 reflections
b = 13.243 (3) Åθ = 2.9–28.8°
c = 24.421 (3) ŵ = 0.29 mm1
β = 95.08 (3)°T = 100 K
V = 2706.6 (12) Å3Block, colorless
Z = 80.20 × 0.19 × 0.18 mm
Data collection top
Rigaku KM-4-CCD Sapphire
diffractometer
3590 reflections with I > 2σ(I)
/w scansRint = 0.087
Absorption correction: analyticalθmax = 28.9°, θmin = 2.9°
Tmin = 0.789, Tmax = 0.879h = 811
24472 measured reflectionsk = 1717
6671 independent reflectionsl = 3232
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0297P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6671 reflectionsΔρmax = 0.46 e Å3
379 parametersΔρmin = 0.48 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.91536 (8)0.24177 (5)0.71555 (3)0.02375 (18)
Cl20.42052 (8)1.21720 (5)0.73040 (3)0.02464 (18)
O10.5546 (3)0.50085 (14)0.60208 (8)0.0307 (5)
H1O0.5679100.4471390.6209820.046*
O20.5066 (2)0.56028 (14)0.68382 (8)0.0292 (5)
C10.4911 (3)0.6744 (2)0.60864 (11)0.0170 (6)
C20.4145 (3)0.74426 (19)0.63890 (11)0.0153 (6)
H20.3845620.7267500.6742910.018*
C30.3802 (3)0.84175 (19)0.61755 (11)0.0150 (6)
N10.4195 (3)0.87148 (16)0.56908 (9)0.0178 (5)
C40.4982 (3)0.8052 (2)0.53859 (11)0.0177 (6)
C50.5443 (3)0.8400 (2)0.48721 (11)0.0200 (6)
H50.5196820.9071870.4757510.024*
C60.6231 (3)0.7785 (2)0.45440 (11)0.0238 (7)
H60.6531470.8026190.4201630.029*
C70.6600 (3)0.6794 (2)0.47097 (12)0.0239 (7)
H70.7148850.6369220.4475610.029*
C80.6192 (3)0.6424 (2)0.51988 (11)0.0206 (7)
H80.6459690.5748670.5300080.025*
C90.5369 (3)0.7039 (2)0.55595 (11)0.0169 (6)
C100.5190 (3)0.5733 (2)0.63549 (12)0.0187 (6)
C110.2945 (3)0.91601 (19)0.64906 (11)0.0170 (6)
C120.2209 (3)1.00039 (19)0.62229 (11)0.0201 (6)
H120.2287191.0105920.5841160.024*
C130.1381 (3)1.0676 (2)0.65159 (12)0.0211 (7)
H130.0891911.1248070.6336680.025*
N20.1257 (3)1.05332 (16)0.70514 (9)0.0185 (5)
H2N0.0720841.0988240.7206530.028*
C140.1958 (3)0.9762 (2)0.73233 (12)0.0215 (7)
H140.1860510.9689810.7705930.026*
C150.2825 (3)0.9065 (2)0.70543 (11)0.0207 (7)
H150.3340640.8521840.7252320.025*
C200.9949 (3)0.66492 (19)0.60295 (11)0.0164 (6)
C210.9134 (3)0.73338 (19)0.63219 (11)0.0169 (6)
H210.8748360.7141790.6660930.020*
C220.8871 (3)0.83198 (19)0.61189 (11)0.0165 (6)
N210.9329 (3)0.86286 (16)0.56428 (9)0.0175 (5)
C231.0097 (3)0.7954 (2)0.53355 (11)0.0175 (6)
C241.0549 (3)0.8287 (2)0.48219 (11)0.0229 (7)
H241.0346600.8966730.4712140.028*
C251.1265 (3)0.7656 (2)0.44832 (11)0.0246 (7)
H251.1548350.7890000.4137220.030*
C261.1589 (3)0.6651 (2)0.46451 (12)0.0243 (7)
H261.2083200.6209200.4404720.029*
C271.1202 (3)0.6302 (2)0.51452 (12)0.0229 (7)
H271.1438460.5622580.5247980.028*
C281.0457 (3)0.69371 (19)0.55079 (11)0.0168 (6)
C291.0198 (3)0.5617 (2)0.62803 (11)0.0194 (6)
O201.1530 (2)0.51821 (14)0.61637 (8)0.0287 (5)
H2O1.1702140.4615590.6321580.043*
O210.9256 (3)0.52524 (15)0.65667 (9)0.0366 (6)
C300.8033 (3)0.90785 (19)0.64361 (11)0.0169 (6)
C310.7371 (3)0.9937 (2)0.61695 (12)0.0203 (6)
H310.7466231.0037440.5788560.024*
C320.6582 (3)1.0634 (2)0.64650 (12)0.0220 (7)
H320.6131091.1219010.6287530.026*
N220.6447 (3)1.04891 (16)0.70013 (10)0.0208 (5)
H22N0.5932291.0924520.7178280.031*
C330.7059 (3)0.9683 (2)0.72726 (12)0.0217 (7)
H330.6931800.9603000.7652800.026*
C340.7879 (3)0.8965 (2)0.69967 (11)0.0193 (6)
H340.8336650.8396580.7188690.023*
O1W1.1739 (2)0.33460 (14)0.65140 (8)0.0269 (5)
H1W1.0946780.3162300.6683370.040*
H2W1.2543640.3053810.6680070.040*
O2W0.6212 (2)0.32842 (14)0.64808 (8)0.0280 (5)
H3W0.7123730.3132410.6637830.042*
H4W0.5545540.3097840.6702980.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0252 (4)0.0192 (4)0.0268 (4)0.0030 (3)0.0015 (3)0.0030 (3)
Cl20.0241 (4)0.0191 (4)0.0302 (4)0.0020 (3)0.0010 (3)0.0034 (3)
O10.0588 (15)0.0135 (10)0.0201 (12)0.0112 (10)0.0060 (10)0.0039 (9)
O20.0474 (14)0.0207 (11)0.0205 (12)0.0046 (10)0.0095 (10)0.0040 (9)
C10.0209 (15)0.0166 (14)0.0132 (15)0.0020 (12)0.0009 (12)0.0009 (12)
C20.0181 (14)0.0152 (13)0.0128 (14)0.0015 (12)0.0026 (11)0.0013 (12)
C30.0156 (14)0.0153 (14)0.0138 (15)0.0024 (11)0.0002 (12)0.0001 (11)
N10.0233 (13)0.0164 (12)0.0137 (13)0.0002 (10)0.0019 (10)0.0001 (10)
C40.0196 (15)0.0184 (15)0.0145 (15)0.0039 (12)0.0024 (12)0.0020 (12)
C50.0237 (16)0.0150 (14)0.0210 (16)0.0006 (12)0.0003 (13)0.0025 (12)
C60.0304 (17)0.0256 (17)0.0158 (16)0.0039 (13)0.0035 (13)0.0009 (13)
C70.0288 (17)0.0228 (16)0.0208 (17)0.0020 (13)0.0068 (14)0.0022 (13)
C80.0259 (17)0.0149 (14)0.0213 (17)0.0020 (12)0.0026 (13)0.0008 (12)
C90.0176 (15)0.0179 (14)0.0147 (15)0.0022 (12)0.0006 (12)0.0018 (12)
C100.0215 (16)0.0164 (15)0.0181 (16)0.0034 (12)0.0007 (13)0.0006 (12)
C110.0180 (15)0.0145 (14)0.0181 (16)0.0030 (11)0.0007 (12)0.0009 (12)
C120.0289 (17)0.0152 (14)0.0156 (16)0.0035 (12)0.0010 (13)0.0002 (12)
C130.0278 (17)0.0130 (14)0.0221 (17)0.0025 (12)0.0001 (13)0.0004 (12)
N20.0216 (13)0.0136 (12)0.0204 (14)0.0007 (10)0.0033 (11)0.0030 (10)
C140.0317 (17)0.0151 (15)0.0182 (17)0.0006 (13)0.0060 (13)0.0006 (12)
C150.0274 (17)0.0187 (15)0.0158 (16)0.0001 (13)0.0011 (13)0.0019 (12)
C200.0209 (15)0.0152 (14)0.0128 (15)0.0033 (12)0.0008 (12)0.0015 (11)
C210.0170 (14)0.0193 (15)0.0144 (14)0.0013 (12)0.0011 (11)0.0040 (12)
C220.0189 (15)0.0154 (14)0.0149 (15)0.0019 (12)0.0005 (12)0.0011 (12)
N210.0226 (13)0.0175 (12)0.0123 (13)0.0019 (10)0.0011 (10)0.0011 (10)
C230.0183 (15)0.0208 (15)0.0130 (15)0.0033 (12)0.0021 (12)0.0005 (12)
C240.0272 (17)0.0193 (15)0.0220 (17)0.0005 (13)0.0009 (14)0.0034 (13)
C250.0315 (18)0.0308 (18)0.0120 (15)0.0003 (14)0.0043 (13)0.0013 (13)
C260.0292 (17)0.0231 (16)0.0215 (17)0.0074 (14)0.0074 (13)0.0011 (14)
C270.0262 (17)0.0210 (16)0.0221 (17)0.0050 (13)0.0052 (14)0.0020 (13)
C280.0189 (15)0.0179 (15)0.0135 (15)0.0022 (12)0.0008 (12)0.0018 (11)
C290.0212 (16)0.0189 (15)0.0181 (16)0.0012 (12)0.0016 (13)0.0005 (12)
O200.0341 (12)0.0215 (11)0.0312 (13)0.0100 (10)0.0074 (10)0.0105 (9)
O210.0449 (14)0.0259 (12)0.0427 (15)0.0095 (11)0.0248 (12)0.0130 (10)
C300.0190 (15)0.0132 (14)0.0182 (16)0.0049 (12)0.0001 (12)0.0007 (12)
C310.0256 (16)0.0186 (15)0.0161 (16)0.0018 (12)0.0003 (13)0.0012 (12)
C320.0270 (16)0.0166 (14)0.0220 (17)0.0010 (12)0.0001 (13)0.0056 (13)
N220.0248 (13)0.0132 (12)0.0246 (14)0.0016 (10)0.0042 (11)0.0047 (10)
C330.0274 (17)0.0221 (16)0.0157 (16)0.0023 (13)0.0031 (13)0.0007 (12)
C340.0241 (16)0.0162 (14)0.0177 (17)0.0006 (12)0.0032 (13)0.0011 (12)
O1W0.0324 (12)0.0234 (11)0.0250 (12)0.0071 (9)0.0038 (9)0.0071 (9)
O2W0.0333 (12)0.0223 (11)0.0285 (12)0.0087 (9)0.0027 (10)0.0064 (9)
Geometric parameters (Å, º) top
O1—C101.311 (3)C20—C291.505 (4)
O1—H1O0.8499C21—C221.407 (4)
O2—C101.206 (3)C21—H210.9500
C1—C21.379 (4)C22—N211.322 (3)
C1—C91.430 (4)C22—C301.484 (4)
C1—C101.499 (4)N21—C231.365 (3)
C2—C31.412 (3)C23—C241.413 (4)
C2—H20.9500C23—C281.435 (4)
C3—N11.317 (3)C24—C251.354 (4)
C3—C111.475 (4)C24—H240.9500
N1—C41.360 (3)C25—C261.407 (4)
C4—C51.422 (4)C25—H250.9500
C4—C91.436 (4)C26—C271.372 (4)
C5—C61.355 (4)C26—H260.9500
C5—H50.9500C27—C281.408 (4)
C6—C71.400 (4)C27—H270.9500
C6—H60.9500C29—O211.203 (3)
C7—C81.362 (4)C29—O201.312 (3)
C7—H70.9500O20—H2O0.8500
C8—C91.423 (4)C30—C341.394 (4)
C8—H80.9500C30—C311.400 (4)
C11—C151.395 (4)C31—C321.378 (4)
C11—C121.410 (4)C31—H310.9500
C12—C131.370 (4)C32—N221.338 (3)
C12—H120.9500C32—H320.9500
C13—N21.334 (3)N22—C331.335 (3)
C13—H130.9500N22—H22N0.8601
N2—C141.327 (3)C33—C341.384 (4)
N2—H2N0.8601C33—H330.9500
C14—C151.378 (4)C34—H340.9500
C14—H140.9500O1W—H1W0.8500
C15—H150.9500O1W—H2W0.8499
C20—C211.374 (4)O2W—H3W0.8498
C20—C281.431 (4)O2W—H4W0.8500
C10—O1—H1O107.5C21—C20—C29116.5 (2)
C2—C1—C9118.3 (2)C28—C20—C29124.2 (2)
C2—C1—C10115.3 (2)C20—C21—C22119.9 (2)
C9—C1—C10126.4 (2)C20—C21—H21120.0
C1—C2—C3120.4 (2)C22—C21—H21120.0
C1—C2—H2119.8N21—C22—C21123.2 (2)
C3—C2—H2119.8N21—C22—C30116.0 (2)
N1—C3—C2123.1 (2)C21—C22—C30120.7 (2)
N1—C3—C11116.3 (2)C22—N21—C23118.0 (2)
C2—C3—C11120.6 (2)N21—C23—C24117.4 (3)
C3—N1—C4118.2 (2)N21—C23—C28123.4 (2)
N1—C4—C5117.3 (2)C24—C23—C28119.2 (3)
N1—C4—C9123.4 (3)C25—C24—C23121.2 (3)
C5—C4—C9119.4 (3)C25—C24—H24119.4
C6—C5—C4120.8 (3)C23—C24—H24119.4
C6—C5—H5119.6C24—C25—C26119.8 (3)
C4—C5—H5119.6C24—C25—H25120.1
C5—C6—C7120.0 (3)C26—C25—H25120.1
C5—C6—H6120.0C27—C26—C25120.9 (3)
C7—C6—H6120.0C27—C26—H26119.5
C8—C7—C6121.6 (3)C25—C26—H26119.5
C8—C7—H7119.2C26—C27—C28120.8 (3)
C6—C7—H7119.2C26—C27—H27119.6
C7—C8—C9120.7 (3)C28—C27—H27119.6
C7—C8—H8119.6C27—C28—C20125.8 (2)
C9—C8—H8119.6C27—C28—C23118.0 (3)
C8—C9—C1125.8 (3)C20—C28—C23116.1 (2)
C8—C9—C4117.5 (3)O21—C29—O20124.6 (3)
C1—C9—C4116.7 (2)O21—C29—C20121.7 (3)
O2—C10—O1123.2 (3)O20—C29—C20113.6 (2)
O2—C10—C1122.1 (3)C29—O20—H2O113.8
O1—C10—C1114.6 (2)C34—C30—C31118.5 (3)
C15—C11—C12117.5 (3)C34—C30—C22121.9 (2)
C15—C11—C3122.4 (2)C31—C30—C22119.6 (2)
C12—C11—C3120.1 (2)C32—C31—C30119.3 (3)
C13—C12—C11119.7 (3)C32—C31—H31120.3
C13—C12—H12120.2C30—C31—H31120.3
C11—C12—H12120.2N22—C32—C31120.2 (3)
N2—C13—C12120.5 (3)N22—C32—H32119.9
N2—C13—H13119.8C31—C32—H32119.9
C12—C13—H13119.8C33—N22—C32122.6 (2)
C14—N2—C13122.0 (2)C33—N22—H22N118.4
C14—N2—H2N123.0C32—N22—H22N119.1
C13—N2—H2N114.9N22—C33—C34119.6 (3)
N2—C14—C15120.4 (3)N22—C33—H33120.2
N2—C14—H14119.8C34—C33—H33120.2
C15—C14—H14119.8C33—C34—C30119.8 (3)
C14—C15—C11119.9 (3)C33—C34—H34120.1
C14—C15—H15120.1C30—C34—H34120.1
C11—C15—H15120.1H1W—O1W—H2W105.2
C21—C20—C28119.3 (2)H3W—O2W—H4W105.2
C9—C1—C2—C31.1 (4)C28—C20—C21—C222.8 (4)
C10—C1—C2—C3179.3 (2)C29—C20—C21—C22179.1 (2)
C1—C2—C3—N10.7 (4)C20—C21—C22—N212.2 (4)
C1—C2—C3—C11178.4 (2)C20—C21—C22—C30178.3 (2)
C2—C3—N1—C40.7 (4)C21—C22—N21—C230.1 (4)
C11—C3—N1—C4179.8 (2)C30—C22—N21—C23179.6 (2)
C3—N1—C4—C5177.9 (2)C22—N21—C23—C24178.6 (2)
C3—N1—C4—C91.6 (4)C22—N21—C23—C281.3 (4)
N1—C4—C5—C6179.9 (2)N21—C23—C24—C25177.7 (2)
C9—C4—C5—C60.5 (4)C28—C23—C24—C252.2 (4)
C4—C5—C6—C70.1 (4)C23—C24—C25—C260.8 (4)
C5—C6—C7—C80.2 (4)C24—C25—C26—C270.6 (4)
C6—C7—C8—C90.0 (4)C25—C26—C27—C280.5 (4)
C7—C8—C9—C1178.5 (3)C26—C27—C28—C20177.7 (3)
C7—C8—C9—C40.4 (4)C26—C27—C28—C230.9 (4)
C2—C1—C9—C8178.7 (3)C21—C20—C28—C27175.4 (3)
C10—C1—C9—C80.8 (4)C29—C20—C28—C272.5 (4)
C2—C1—C9—C40.3 (4)C21—C20—C28—C231.5 (4)
C10—C1—C9—C4179.8 (2)C29—C20—C28—C23179.4 (2)
N1—C4—C9—C8179.8 (2)N21—C23—C28—C27177.7 (2)
C5—C4—C9—C80.7 (4)C24—C23—C28—C272.2 (4)
N1—C4—C9—C11.1 (4)N21—C23—C28—C200.5 (4)
C5—C4—C9—C1178.4 (2)C24—C23—C28—C20179.3 (2)
C2—C1—C10—O214.9 (4)C21—C20—C29—O2130.5 (4)
C9—C1—C10—O2164.6 (3)C28—C20—C29—O21147.4 (3)
C2—C1—C10—O1163.9 (2)C21—C20—C29—O20148.3 (2)
C9—C1—C10—O116.5 (4)C28—C20—C29—O2033.8 (4)
N1—C3—C11—C15162.7 (3)N21—C22—C30—C34161.8 (3)
C2—C3—C11—C1518.2 (4)C21—C22—C30—C3418.7 (4)
N1—C3—C11—C1217.3 (4)N21—C22—C30—C3118.2 (4)
C2—C3—C11—C12161.8 (2)C21—C22—C30—C31161.3 (2)
C15—C11—C12—C131.7 (4)C34—C30—C31—C320.6 (4)
C3—C11—C12—C13178.3 (2)C22—C30—C31—C32179.4 (2)
C11—C12—C13—N20.5 (4)C30—C31—C32—N220.1 (4)
C12—C13—N2—C142.0 (4)C31—C32—N22—C330.2 (4)
C13—N2—C14—C151.1 (4)C32—N22—C33—C340.5 (4)
N2—C14—C15—C111.1 (4)N22—C33—C34—C301.3 (4)
C12—C11—C15—C142.5 (4)C31—C30—C34—C331.3 (4)
C3—C11—C15—C14177.5 (3)C22—C30—C34—C33178.7 (2)
 

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