Buy article online - an online subscription or single-article purchase is required to access this article.
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:O;κ2O: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
CCDC references: 1994495; 1994494
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]·2H2O | Z = 1 |
Mr = 634.09 | F(000) = 327 |
Triclinic, P1 | Dx = 1.503 Mg m−3 |
a = 8.647 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.819 (3) Å | Cell parameters from 3141 reflections |
c = 10.125 (2) Å | θ = 2.2–25.5° |
α = 70.58 (2)° | µ = 0.84 mm−1 |
β = 79.61 (3)° | T = 100 K |
γ = 75.26 (3)° | Block, blue/green |
V = 700.3 (4) Å3 | 0.20 × 0.18 × 0.15 mm |
Data collection top
Oxford Diffraction Xcalibur Ruby diffractometer | 2397 reflections with I > 2σ(I) |
CCD scans | Rint = 0.031 |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2017) | θmax = 28.8°, θmin = 2.2° |
Tmin = 0.867, Tmax = 0.940 | h = −10→11 |
4791 measured reflections | k = −11→10 |
3141 independent reflections | l = −13→11 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H-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 reflections | Δρmax = 0.92 e Å−3 |
196 parameters | Δρmin = −0.36 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.500000 | 1.000000 | 0.000000 | 0.01642 (17) | |
O1 | 0.3010 (2) | 0.9513 (2) | 0.1250 (2) | 0.0181 (5) | |
O2 | 0.2854 (3) | 0.7167 (3) | 0.0924 (2) | 0.0321 (6) | |
O1W | 0.2261 (3) | 0.4049 (2) | 0.1788 (2) | 0.0315 (6) | |
H1WA | 0.237114 | 0.501935 | 0.166367 | 0.047* | |
H1WB | 0.153431 | 0.389267 | 0.247677 | 0.047* | |
O2W | 0.5056 (2) | 0.8188 (2) | −0.1296 (2) | 0.0231 (5) | |
H2WA | 0.444246 | 0.766755 | −0.064635 | 0.035* | |
H2WB | 0.585136 | 0.749325 | −0.152145 | 0.035* | |
N1 | 0.0033 (3) | 0.6870 (3) | 0.5775 (2) | 0.0160 (5) | |
N2 | 0.3666 (3) | 0.1778 (3) | 0.8565 (2) | 0.0168 (5) | |
C1 | 0.1575 (3) | 0.7750 (3) | 0.3026 (3) | 0.0155 (6) | |
C2 | 0.0135 (3) | 0.8792 (3) | 0.3388 (3) | 0.0154 (6) | |
C3 | −0.0599 (3) | 1.0275 (3) | 0.2441 (3) | 0.0193 (7) | |
H3 | −0.012569 | 1.061998 | 0.149708 | 0.023* | |
C4 | −0.1986 (4) | 1.1217 (4) | 0.2876 (3) | 0.0223 (7) | |
H4 | −0.247212 | 1.221336 | 0.223372 | 0.027* | |
C5 | −0.2697 (4) | 1.0718 (4) | 0.4268 (3) | 0.0218 (7) | |
H5 | −0.366016 | 1.138649 | 0.455546 | 0.026* | |
C6 | −0.2034 (3) | 0.9299 (3) | 0.5214 (3) | 0.0185 (6) | |
H6 | −0.253362 | 0.898440 | 0.615121 | 0.022* | |
C7 | −0.0592 (3) | 0.8285 (3) | 0.4800 (3) | 0.0155 (6) | |
C8 | 0.1395 (3) | 0.5940 (3) | 0.5397 (3) | 0.0158 (6) | |
C9 | 0.2181 (3) | 0.6343 (3) | 0.4019 (3) | 0.0175 (6) | |
H9 | 0.313843 | 0.562980 | 0.378152 | 0.021* | |
C10 | 0.2543 (3) | 0.8177 (4) | 0.1587 (3) | 0.0183 (7) | |
C11 | 0.2129 (3) | 0.4456 (3) | 0.6501 (3) | 0.0164 (6) | |
C12 | 0.3270 (3) | 0.3172 (3) | 0.6151 (3) | 0.0181 (6) | |
H12 | 0.354292 | 0.319308 | 0.519398 | 0.022* | |
C13 | 0.3997 (3) | 0.1878 (3) | 0.7199 (3) | 0.0179 (6) | |
H13 | 0.476818 | 0.101558 | 0.694121 | 0.022* | |
C14 | 0.2525 (3) | 0.2975 (3) | 0.8913 (3) | 0.0193 (7) | |
H14 | 0.224036 | 0.289304 | 0.988125 | 0.023* | |
C15 | 0.1750 (3) | 0.4312 (3) | 0.7933 (3) | 0.0188 (6) | |
H15 | 0.095966 | 0.513638 | 0.822671 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0165 (3) | 0.0143 (3) | 0.0107 (3) | −0.0012 (2) | 0.0006 (2) | 0.0037 (2) |
O1 | 0.0182 (11) | 0.0133 (10) | 0.0171 (10) | −0.0033 (9) | 0.0018 (8) | 0.0009 (8) |
O2 | 0.0469 (15) | 0.0266 (12) | 0.0241 (12) | −0.0176 (11) | 0.0144 (11) | −0.0112 (11) |
O1W | 0.0348 (14) | 0.0218 (12) | 0.0305 (13) | −0.0074 (10) | 0.0149 (11) | −0.0069 (10) |
O2W | 0.0216 (11) | 0.0222 (11) | 0.0195 (11) | −0.0042 (9) | 0.0032 (9) | −0.0015 (9) |
N1 | 0.0161 (13) | 0.0146 (12) | 0.0135 (12) | −0.0017 (10) | −0.0018 (10) | −0.0006 (10) |
N2 | 0.0165 (13) | 0.0162 (12) | 0.0123 (12) | −0.0013 (10) | 0.0012 (10) | −0.0005 (10) |
C1 | 0.0174 (15) | 0.0165 (15) | 0.0116 (14) | −0.0049 (12) | −0.0016 (12) | −0.0020 (12) |
C2 | 0.0155 (15) | 0.0146 (14) | 0.0145 (14) | −0.0047 (12) | −0.0016 (12) | −0.0011 (12) |
C3 | 0.0210 (16) | 0.0187 (15) | 0.0146 (14) | −0.0031 (13) | −0.0034 (13) | −0.0004 (12) |
C4 | 0.0230 (17) | 0.0168 (15) | 0.0242 (16) | −0.0011 (13) | −0.0091 (14) | −0.0012 (13) |
C5 | 0.0172 (16) | 0.0198 (16) | 0.0267 (17) | 0.0006 (13) | −0.0028 (13) | −0.0080 (14) |
C6 | 0.0174 (15) | 0.0184 (15) | 0.0171 (15) | −0.0030 (12) | 0.0010 (12) | −0.0042 (12) |
C7 | 0.0165 (15) | 0.0139 (14) | 0.0145 (14) | −0.0020 (12) | −0.0014 (12) | −0.0032 (12) |
C8 | 0.0189 (15) | 0.0145 (14) | 0.0119 (14) | −0.0064 (12) | 0.0000 (12) | 0.0002 (12) |
C9 | 0.0179 (15) | 0.0153 (15) | 0.0152 (14) | −0.0001 (12) | −0.0004 (12) | −0.0025 (12) |
C10 | 0.0164 (15) | 0.0184 (16) | 0.0142 (14) | 0.0002 (12) | −0.0025 (12) | 0.0003 (12) |
C11 | 0.0181 (15) | 0.0163 (15) | 0.0130 (14) | −0.0049 (12) | −0.0038 (12) | −0.0001 (12) |
C12 | 0.0213 (16) | 0.0185 (15) | 0.0107 (14) | −0.0026 (13) | 0.0009 (12) | −0.0022 (12) |
C13 | 0.0198 (16) | 0.0161 (15) | 0.0138 (14) | −0.0012 (12) | 0.0006 (12) | −0.0025 (12) |
C14 | 0.0222 (16) | 0.0197 (15) | 0.0118 (14) | −0.0028 (13) | 0.0009 (13) | −0.0020 (12) |
C15 | 0.0195 (16) | 0.0176 (15) | 0.0145 (14) | 0.0004 (12) | 0.0005 (12) | −0.0027 (12) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.994 (2) | C2—C7 | 1.426 (4) |
Cu1—O1i | 1.994 (2) | C3—C4 | 1.367 (4) |
Cu1—N2ii | 2.017 (2) | C3—H3 | 0.9500 |
Cu1—N2iii | 2.017 (2) | C4—C5 | 1.403 (4) |
Cu1—O2W | 2.368 (2) | C4—H4 | 0.9500 |
Cu1—O2Wi | 2.368 (2) | C5—C6 | 1.359 (4) |
O1—C10 | 1.262 (3) | C5—H5 | 0.9500 |
O2—C10 | 1.235 (3) | C6—C7 | 1.422 (4) |
O1W—H1WA | 0.8499 | C6—H6 | 0.9500 |
O1W—H1WB | 0.8500 | C8—C9 | 1.410 (4) |
O2W—H2WA | 0.8500 | C8—C11 | 1.492 (4) |
O2W—H2WB | 0.8500 | C9—H9 | 0.9500 |
N1—C8 | 1.327 (4) | C11—C15 | 1.397 (4) |
N1—C7 | 1.362 (3) | C11—C12 | 1.398 (4) |
N2—C13 | 1.339 (4) | C12—C13 | 1.376 (4) |
N2—C14 | 1.344 (4) | C12—H12 | 0.9500 |
C1—C9 | 1.362 (4) | C13—H13 | 0.9500 |
C1—C2 | 1.416 (4) | C14—C15 | 1.372 (4) |
C1—C10 | 1.524 (4) | C14—H14 | 0.9500 |
C2—C3 | 1.413 (4) | C15—H15 | 0.9500 |
| | | |
O1—Cu1—O1i | 180.0 | C5—C4—H4 | 119.8 |
O1—Cu1—N2ii | 89.53 (9) | C6—C5—C4 | 121.3 (3) |
O1i—Cu1—N2ii | 90.47 (9) | C6—C5—H5 | 119.3 |
O1—Cu1—N2iii | 90.47 (9) | C4—C5—H5 | 119.3 |
O1i—Cu1—N2iii | 89.53 (9) | C5—C6—C7 | 120.0 (3) |
N2ii—Cu1—N2iii | 180.0 | C5—C6—H6 | 120.0 |
O1—Cu1—O2W | 95.24 (8) | C7—C6—H6 | 120.0 |
O1i—Cu1—O2W | 84.76 (8) | N1—C7—C6 | 118.3 (2) |
N2ii—Cu1—O2W | 92.18 (9) | N1—C7—C2 | 122.9 (3) |
N2iii—Cu1—O2W | 87.82 (9) | C6—C7—C2 | 118.8 (2) |
O1—Cu1—O2Wi | 84.76 (8) | N1—C8—C9 | 122.3 (2) |
O1i—Cu1—O2Wi | 95.24 (8) | N1—C8—C11 | 117.8 (2) |
N2ii—Cu1—O2Wi | 87.82 (9) | C9—C8—C11 | 119.8 (3) |
N2iii—Cu1—O2Wi | 92.18 (9) | C1—C9—C8 | 120.3 (3) |
O2W—Cu1—O2Wi | 180.0 | C1—C9—H9 | 119.8 |
C10—O1—Cu1 | 125.15 (19) | C8—C9—H9 | 119.8 |
H1WA—O1W—H1WB | 104.1 | O2—C10—O1 | 127.6 (3) |
Cu1—O2W—H2WA | 91.1 | O2—C10—C1 | 117.9 (2) |
Cu1—O2W—H2WB | 128.4 | O1—C10—C1 | 114.5 (3) |
H2WA—O2W—H2WB | 108.3 | C15—C11—C12 | 116.9 (3) |
C8—N1—C7 | 118.3 (2) | C15—C11—C8 | 121.5 (3) |
C13—N2—C14 | 117.5 (2) | C12—C11—C8 | 121.6 (3) |
C13—N2—Cu1iv | 120.14 (19) | C13—C12—C11 | 119.7 (3) |
C14—N2—Cu1iv | 122.07 (19) | C13—C12—H12 | 120.2 |
C9—C1—C2 | 119.3 (3) | C11—C12—H12 | 120.2 |
C9—C1—C10 | 117.8 (3) | N2—C13—C12 | 123.0 (3) |
C2—C1—C10 | 122.9 (2) | N2—C13—H13 | 118.5 |
C3—C2—C1 | 123.9 (3) | C12—C13—H13 | 118.5 |
C3—C2—C7 | 119.2 (3) | N2—C14—C15 | 123.0 (3) |
C1—C2—C7 | 116.8 (2) | N2—C14—H14 | 118.5 |
C4—C3—C2 | 120.3 (3) | C15—C14—H14 | 118.5 |
C4—C3—H3 | 119.8 | C14—C15—C11 | 119.8 (3) |
C2—C3—H3 | 119.8 | C14—C15—H15 | 120.1 |
C3—C4—C5 | 120.3 (3) | C11—C15—H15 | 120.1 |
C3—C4—H4 | 119.8 | | |
| | | |
C9—C1—C2—C3 | −179.9 (3) | C11—C8—C9—C1 | −175.9 (2) |
C10—C1—C2—C3 | 3.8 (4) | Cu1—O1—C10—O2 | −25.3 (4) |
C9—C1—C2—C7 | 0.2 (4) | Cu1—O1—C10—C1 | 150.54 (18) |
C10—C1—C2—C7 | −176.2 (3) | C9—C1—C10—O2 | 58.0 (4) |
C1—C2—C3—C4 | −179.7 (3) | C2—C1—C10—O2 | −125.6 (3) |
C7—C2—C3—C4 | 0.3 (4) | C9—C1—C10—O1 | −118.3 (3) |
C2—C3—C4—C5 | −0.1 (5) | C2—C1—C10—O1 | 58.1 (4) |
C3—C4—C5—C6 | −0.1 (5) | N1—C8—C11—C15 | −20.8 (4) |
C4—C5—C6—C7 | 0.0 (4) | C9—C8—C11—C15 | 156.9 (3) |
C8—N1—C7—C6 | −178.7 (3) | N1—C8—C11—C12 | 161.5 (3) |
C8—N1—C7—C2 | 1.3 (4) | C9—C8—C11—C12 | −20.7 (4) |
C5—C6—C7—N1 | −179.8 (3) | C15—C11—C12—C13 | −2.1 (4) |
C5—C6—C7—C2 | 0.3 (4) | C8—C11—C12—C13 | 175.6 (2) |
C3—C2—C7—N1 | 179.6 (3) | C14—N2—C13—C12 | 2.7 (4) |
C1—C2—C7—N1 | −0.4 (4) | Cu1iv—N2—C13—C12 | −171.7 (2) |
C3—C2—C7—C6 | −0.4 (4) | C11—C12—C13—N2 | −0.1 (4) |
C1—C2—C7—C6 | 179.6 (3) | C13—N2—C14—C15 | −3.0 (4) |
C7—N1—C8—C9 | −1.9 (4) | Cu1iv—N2—C14—C15 | 171.2 (2) |
C7—N1—C8—C11 | 175.7 (2) | N2—C14—C15—C11 | 0.8 (5) |
C2—C1—C9—C8 | −0.8 (4) | C12—C11—C15—C14 | 1.8 (4) |
C10—C1—C9—C8 | 175.7 (3) | C8—C11—C15—C14 | −176.0 (3) |
N1—C8—C9—C1 | 1.8 (4) | | |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z−1; (iv) x, y−1, z+1. |
4-(4-Carboxyquinolin-2-yl)pyridinium chloride monohydrate (kk6dc)
top
Crystal data top
C15H11N2O2+·Cl−·H2O | F(000) = 1264 |
Mr = 304.72 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.402 (3) Å | Cell parameters from 5674 reflections |
b = 13.243 (3) Å | θ = 2.9–28.8° |
c = 24.421 (3) Å | µ = 0.29 mm−1 |
β = 95.08 (3)° | T = 100 K |
V = 2706.6 (12) Å3 | Block, colorless |
Z = 8 | 0.20 × 0.19 × 0.18 mm |
Data collection top
Rigaku KM-4-CCD Sapphire diffractometer | 3590 reflections with I > 2σ(I) |
/w scans | Rint = 0.087 |
Absorption correction: analytical | θmax = 28.9°, θmin = 2.9° |
Tmin = 0.789, Tmax = 0.879 | h = −8→11 |
24472 measured reflections | k = −17→17 |
6671 independent reflections | l = −32→32 |
Refinement top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H-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 reflections | Δρmax = 0.46 e Å−3 |
379 parameters | Δρmin = −0.48 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.91536 (8) | 0.24177 (5) | 0.71555 (3) | 0.02375 (18) | |
Cl2 | 0.42052 (8) | 1.21720 (5) | 0.73040 (3) | 0.02464 (18) | |
O1 | 0.5546 (3) | 0.50085 (14) | 0.60208 (8) | 0.0307 (5) | |
H1O | 0.567910 | 0.447139 | 0.620982 | 0.046* | |
O2 | 0.5066 (2) | 0.56028 (14) | 0.68382 (8) | 0.0292 (5) | |
C1 | 0.4911 (3) | 0.6744 (2) | 0.60864 (11) | 0.0170 (6) | |
C2 | 0.4145 (3) | 0.74426 (19) | 0.63890 (11) | 0.0153 (6) | |
H2 | 0.384562 | 0.726750 | 0.674291 | 0.018* | |
C3 | 0.3802 (3) | 0.84175 (19) | 0.61755 (11) | 0.0150 (6) | |
N1 | 0.4195 (3) | 0.87148 (16) | 0.56908 (9) | 0.0178 (5) | |
C4 | 0.4982 (3) | 0.8052 (2) | 0.53859 (11) | 0.0177 (6) | |
C5 | 0.5443 (3) | 0.8400 (2) | 0.48721 (11) | 0.0200 (6) | |
H5 | 0.519682 | 0.907187 | 0.475751 | 0.024* | |
C6 | 0.6231 (3) | 0.7785 (2) | 0.45440 (11) | 0.0238 (7) | |
H6 | 0.653147 | 0.802619 | 0.420163 | 0.029* | |
C7 | 0.6600 (3) | 0.6794 (2) | 0.47097 (12) | 0.0239 (7) | |
H7 | 0.714885 | 0.636922 | 0.447561 | 0.029* | |
C8 | 0.6192 (3) | 0.6424 (2) | 0.51988 (11) | 0.0206 (7) | |
H8 | 0.645969 | 0.574867 | 0.530008 | 0.025* | |
C9 | 0.5369 (3) | 0.7039 (2) | 0.55595 (11) | 0.0169 (6) | |
C10 | 0.5190 (3) | 0.5733 (2) | 0.63549 (12) | 0.0187 (6) | |
C11 | 0.2945 (3) | 0.91601 (19) | 0.64906 (11) | 0.0170 (6) | |
C12 | 0.2209 (3) | 1.00039 (19) | 0.62229 (11) | 0.0201 (6) | |
H12 | 0.228719 | 1.010592 | 0.584116 | 0.024* | |
C13 | 0.1381 (3) | 1.0676 (2) | 0.65159 (12) | 0.0211 (7) | |
H13 | 0.089191 | 1.124807 | 0.633668 | 0.025* | |
N2 | 0.1257 (3) | 1.05332 (16) | 0.70514 (9) | 0.0185 (5) | |
H2N | 0.072084 | 1.098824 | 0.720653 | 0.028* | |
C14 | 0.1958 (3) | 0.9762 (2) | 0.73233 (12) | 0.0215 (7) | |
H14 | 0.186051 | 0.968981 | 0.770593 | 0.026* | |
C15 | 0.2825 (3) | 0.9065 (2) | 0.70543 (11) | 0.0207 (7) | |
H15 | 0.334064 | 0.852184 | 0.725232 | 0.025* | |
C20 | 0.9949 (3) | 0.66492 (19) | 0.60295 (11) | 0.0164 (6) | |
C21 | 0.9134 (3) | 0.73338 (19) | 0.63219 (11) | 0.0169 (6) | |
H21 | 0.874836 | 0.714179 | 0.666093 | 0.020* | |
C22 | 0.8871 (3) | 0.83198 (19) | 0.61189 (11) | 0.0165 (6) | |
N21 | 0.9329 (3) | 0.86286 (16) | 0.56428 (9) | 0.0175 (5) | |
C23 | 1.0097 (3) | 0.7954 (2) | 0.53355 (11) | 0.0175 (6) | |
C24 | 1.0549 (3) | 0.8287 (2) | 0.48219 (11) | 0.0229 (7) | |
H24 | 1.034660 | 0.896673 | 0.471214 | 0.028* | |
C25 | 1.1265 (3) | 0.7656 (2) | 0.44832 (11) | 0.0246 (7) | |
H25 | 1.154835 | 0.789000 | 0.413722 | 0.030* | |
C26 | 1.1589 (3) | 0.6651 (2) | 0.46451 (12) | 0.0243 (7) | |
H26 | 1.208320 | 0.620920 | 0.440472 | 0.029* | |
C27 | 1.1202 (3) | 0.6302 (2) | 0.51452 (12) | 0.0229 (7) | |
H27 | 1.143846 | 0.562258 | 0.524798 | 0.028* | |
C28 | 1.0457 (3) | 0.69371 (19) | 0.55079 (11) | 0.0168 (6) | |
C29 | 1.0198 (3) | 0.5617 (2) | 0.62803 (11) | 0.0194 (6) | |
O20 | 1.1530 (2) | 0.51821 (14) | 0.61637 (8) | 0.0287 (5) | |
H2O | 1.170214 | 0.461559 | 0.632158 | 0.043* | |
O21 | 0.9256 (3) | 0.52524 (15) | 0.65667 (9) | 0.0366 (6) | |
C30 | 0.8033 (3) | 0.90785 (19) | 0.64361 (11) | 0.0169 (6) | |
C31 | 0.7371 (3) | 0.9937 (2) | 0.61695 (12) | 0.0203 (6) | |
H31 | 0.746623 | 1.003744 | 0.578856 | 0.024* | |
C32 | 0.6582 (3) | 1.0634 (2) | 0.64650 (12) | 0.0220 (7) | |
H32 | 0.613109 | 1.121901 | 0.628753 | 0.026* | |
N22 | 0.6447 (3) | 1.04891 (16) | 0.70013 (10) | 0.0208 (5) | |
H22N | 0.593229 | 1.092452 | 0.717828 | 0.031* | |
C33 | 0.7059 (3) | 0.9683 (2) | 0.72726 (12) | 0.0217 (7) | |
H33 | 0.693180 | 0.960300 | 0.765280 | 0.026* | |
C34 | 0.7879 (3) | 0.8965 (2) | 0.69967 (11) | 0.0193 (6) | |
H34 | 0.833665 | 0.839658 | 0.718869 | 0.023* | |
O1W | 1.1739 (2) | 0.33460 (14) | 0.65140 (8) | 0.0269 (5) | |
H1W | 1.094678 | 0.316230 | 0.668337 | 0.040* | |
H2W | 1.254364 | 0.305381 | 0.668007 | 0.040* | |
O2W | 0.6212 (2) | 0.32842 (14) | 0.64808 (8) | 0.0280 (5) | |
H3W | 0.712373 | 0.313241 | 0.663783 | 0.042* | |
H4W | 0.554554 | 0.309784 | 0.670298 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0252 (4) | 0.0192 (4) | 0.0268 (4) | 0.0030 (3) | 0.0015 (3) | −0.0030 (3) |
Cl2 | 0.0241 (4) | 0.0191 (4) | 0.0302 (4) | 0.0020 (3) | −0.0010 (3) | −0.0034 (3) |
O1 | 0.0588 (15) | 0.0135 (10) | 0.0201 (12) | 0.0112 (10) | 0.0060 (10) | 0.0039 (9) |
O2 | 0.0474 (14) | 0.0207 (11) | 0.0205 (12) | 0.0046 (10) | 0.0095 (10) | 0.0040 (9) |
C1 | 0.0209 (15) | 0.0166 (14) | 0.0132 (15) | −0.0020 (12) | −0.0009 (12) | 0.0009 (12) |
C2 | 0.0181 (14) | 0.0152 (13) | 0.0128 (14) | −0.0015 (12) | 0.0026 (11) | 0.0013 (12) |
C3 | 0.0156 (14) | 0.0153 (14) | 0.0138 (15) | −0.0024 (11) | −0.0002 (12) | 0.0001 (11) |
N1 | 0.0233 (13) | 0.0164 (12) | 0.0137 (13) | −0.0002 (10) | 0.0019 (10) | −0.0001 (10) |
C4 | 0.0196 (15) | 0.0184 (15) | 0.0145 (15) | −0.0039 (12) | −0.0024 (12) | 0.0020 (12) |
C5 | 0.0237 (16) | 0.0150 (14) | 0.0210 (16) | −0.0006 (12) | −0.0003 (13) | 0.0025 (12) |
C6 | 0.0304 (17) | 0.0256 (17) | 0.0158 (16) | −0.0039 (13) | 0.0035 (13) | 0.0009 (13) |
C7 | 0.0288 (17) | 0.0228 (16) | 0.0208 (17) | 0.0020 (13) | 0.0068 (14) | −0.0022 (13) |
C8 | 0.0259 (17) | 0.0149 (14) | 0.0213 (17) | 0.0020 (12) | 0.0026 (13) | −0.0008 (12) |
C9 | 0.0176 (15) | 0.0179 (14) | 0.0147 (15) | −0.0022 (12) | −0.0006 (12) | −0.0018 (12) |
C10 | 0.0215 (16) | 0.0164 (15) | 0.0181 (16) | 0.0034 (12) | 0.0007 (13) | −0.0006 (12) |
C11 | 0.0180 (15) | 0.0145 (14) | 0.0181 (16) | −0.0030 (11) | 0.0007 (12) | −0.0009 (12) |
C12 | 0.0289 (17) | 0.0152 (14) | 0.0156 (16) | −0.0035 (12) | −0.0010 (13) | 0.0002 (12) |
C13 | 0.0278 (17) | 0.0130 (14) | 0.0221 (17) | 0.0025 (12) | 0.0001 (13) | 0.0004 (12) |
N2 | 0.0216 (13) | 0.0136 (12) | 0.0204 (14) | 0.0007 (10) | 0.0033 (11) | −0.0030 (10) |
C14 | 0.0317 (17) | 0.0151 (15) | 0.0182 (17) | −0.0006 (13) | 0.0060 (13) | 0.0006 (12) |
C15 | 0.0274 (17) | 0.0187 (15) | 0.0158 (16) | 0.0001 (13) | 0.0011 (13) | 0.0019 (12) |
C20 | 0.0209 (15) | 0.0152 (14) | 0.0128 (15) | −0.0033 (12) | −0.0008 (12) | −0.0015 (11) |
C21 | 0.0170 (14) | 0.0193 (15) | 0.0144 (14) | −0.0013 (12) | 0.0011 (11) | 0.0040 (12) |
C22 | 0.0189 (15) | 0.0154 (14) | 0.0149 (15) | −0.0019 (12) | −0.0005 (12) | −0.0011 (12) |
N21 | 0.0226 (13) | 0.0175 (12) | 0.0123 (13) | −0.0019 (10) | 0.0011 (10) | 0.0011 (10) |
C23 | 0.0183 (15) | 0.0208 (15) | 0.0130 (15) | −0.0033 (12) | −0.0021 (12) | −0.0005 (12) |
C24 | 0.0272 (17) | 0.0193 (15) | 0.0220 (17) | −0.0005 (13) | 0.0009 (14) | 0.0034 (13) |
C25 | 0.0315 (18) | 0.0308 (18) | 0.0120 (15) | −0.0003 (14) | 0.0043 (13) | 0.0013 (13) |
C26 | 0.0292 (17) | 0.0231 (16) | 0.0215 (17) | 0.0074 (14) | 0.0074 (13) | −0.0011 (14) |
C27 | 0.0262 (17) | 0.0210 (16) | 0.0221 (17) | 0.0050 (13) | 0.0052 (14) | 0.0020 (13) |
C28 | 0.0189 (15) | 0.0179 (15) | 0.0135 (15) | −0.0022 (12) | 0.0008 (12) | −0.0018 (11) |
C29 | 0.0212 (16) | 0.0189 (15) | 0.0181 (16) | 0.0012 (12) | 0.0016 (13) | 0.0005 (12) |
O20 | 0.0341 (12) | 0.0215 (11) | 0.0312 (13) | 0.0100 (10) | 0.0074 (10) | 0.0105 (9) |
O21 | 0.0449 (14) | 0.0259 (12) | 0.0427 (15) | 0.0095 (11) | 0.0248 (12) | 0.0130 (10) |
C30 | 0.0190 (15) | 0.0132 (14) | 0.0182 (16) | −0.0049 (12) | −0.0001 (12) | −0.0007 (12) |
C31 | 0.0256 (16) | 0.0186 (15) | 0.0161 (16) | −0.0018 (12) | −0.0003 (13) | 0.0012 (12) |
C32 | 0.0270 (16) | 0.0166 (14) | 0.0220 (17) | 0.0010 (12) | 0.0001 (13) | 0.0056 (13) |
N22 | 0.0248 (13) | 0.0132 (12) | 0.0246 (14) | 0.0016 (10) | 0.0042 (11) | −0.0047 (10) |
C33 | 0.0274 (17) | 0.0221 (16) | 0.0157 (16) | −0.0023 (13) | 0.0031 (13) | 0.0007 (12) |
C34 | 0.0241 (16) | 0.0162 (14) | 0.0177 (17) | 0.0006 (12) | 0.0032 (13) | 0.0011 (12) |
O1W | 0.0324 (12) | 0.0234 (11) | 0.0250 (12) | 0.0071 (9) | 0.0038 (9) | 0.0071 (9) |
O2W | 0.0333 (12) | 0.0223 (11) | 0.0285 (12) | 0.0087 (9) | 0.0027 (10) | 0.0064 (9) |
Geometric parameters (Å, º) top
O1—C10 | 1.311 (3) | C20—C29 | 1.505 (4) |
O1—H1O | 0.8499 | C21—C22 | 1.407 (4) |
O2—C10 | 1.206 (3) | C21—H21 | 0.9500 |
C1—C2 | 1.379 (4) | C22—N21 | 1.322 (3) |
C1—C9 | 1.430 (4) | C22—C30 | 1.484 (4) |
C1—C10 | 1.499 (4) | N21—C23 | 1.365 (3) |
C2—C3 | 1.412 (3) | C23—C24 | 1.413 (4) |
C2—H2 | 0.9500 | C23—C28 | 1.435 (4) |
C3—N1 | 1.317 (3) | C24—C25 | 1.354 (4) |
C3—C11 | 1.475 (4) | C24—H24 | 0.9500 |
N1—C4 | 1.360 (3) | C25—C26 | 1.407 (4) |
C4—C5 | 1.422 (4) | C25—H25 | 0.9500 |
C4—C9 | 1.436 (4) | C26—C27 | 1.372 (4) |
C5—C6 | 1.355 (4) | C26—H26 | 0.9500 |
C5—H5 | 0.9500 | C27—C28 | 1.408 (4) |
C6—C7 | 1.400 (4) | C27—H27 | 0.9500 |
C6—H6 | 0.9500 | C29—O21 | 1.203 (3) |
C7—C8 | 1.362 (4) | C29—O20 | 1.312 (3) |
C7—H7 | 0.9500 | O20—H2O | 0.8500 |
C8—C9 | 1.423 (4) | C30—C34 | 1.394 (4) |
C8—H8 | 0.9500 | C30—C31 | 1.400 (4) |
C11—C15 | 1.395 (4) | C31—C32 | 1.378 (4) |
C11—C12 | 1.410 (4) | C31—H31 | 0.9500 |
C12—C13 | 1.370 (4) | C32—N22 | 1.338 (3) |
C12—H12 | 0.9500 | C32—H32 | 0.9500 |
C13—N2 | 1.334 (3) | N22—C33 | 1.335 (3) |
C13—H13 | 0.9500 | N22—H22N | 0.8601 |
N2—C14 | 1.327 (3) | C33—C34 | 1.384 (4) |
N2—H2N | 0.8601 | C33—H33 | 0.9500 |
C14—C15 | 1.378 (4) | C34—H34 | 0.9500 |
C14—H14 | 0.9500 | O1W—H1W | 0.8500 |
C15—H15 | 0.9500 | O1W—H2W | 0.8499 |
C20—C21 | 1.374 (4) | O2W—H3W | 0.8498 |
C20—C28 | 1.431 (4) | O2W—H4W | 0.8500 |
| | | |
C10—O1—H1O | 107.5 | C21—C20—C29 | 116.5 (2) |
C2—C1—C9 | 118.3 (2) | C28—C20—C29 | 124.2 (2) |
C2—C1—C10 | 115.3 (2) | C20—C21—C22 | 119.9 (2) |
C9—C1—C10 | 126.4 (2) | C20—C21—H21 | 120.0 |
C1—C2—C3 | 120.4 (2) | C22—C21—H21 | 120.0 |
C1—C2—H2 | 119.8 | N21—C22—C21 | 123.2 (2) |
C3—C2—H2 | 119.8 | N21—C22—C30 | 116.0 (2) |
N1—C3—C2 | 123.1 (2) | C21—C22—C30 | 120.7 (2) |
N1—C3—C11 | 116.3 (2) | C22—N21—C23 | 118.0 (2) |
C2—C3—C11 | 120.6 (2) | N21—C23—C24 | 117.4 (3) |
C3—N1—C4 | 118.2 (2) | N21—C23—C28 | 123.4 (2) |
N1—C4—C5 | 117.3 (2) | C24—C23—C28 | 119.2 (3) |
N1—C4—C9 | 123.4 (3) | C25—C24—C23 | 121.2 (3) |
C5—C4—C9 | 119.4 (3) | C25—C24—H24 | 119.4 |
C6—C5—C4 | 120.8 (3) | C23—C24—H24 | 119.4 |
C6—C5—H5 | 119.6 | C24—C25—C26 | 119.8 (3) |
C4—C5—H5 | 119.6 | C24—C25—H25 | 120.1 |
C5—C6—C7 | 120.0 (3) | C26—C25—H25 | 120.1 |
C5—C6—H6 | 120.0 | C27—C26—C25 | 120.9 (3) |
C7—C6—H6 | 120.0 | C27—C26—H26 | 119.5 |
C8—C7—C6 | 121.6 (3) | C25—C26—H26 | 119.5 |
C8—C7—H7 | 119.2 | C26—C27—C28 | 120.8 (3) |
C6—C7—H7 | 119.2 | C26—C27—H27 | 119.6 |
C7—C8—C9 | 120.7 (3) | C28—C27—H27 | 119.6 |
C7—C8—H8 | 119.6 | C27—C28—C20 | 125.8 (2) |
C9—C8—H8 | 119.6 | C27—C28—C23 | 118.0 (3) |
C8—C9—C1 | 125.8 (3) | C20—C28—C23 | 116.1 (2) |
C8—C9—C4 | 117.5 (3) | O21—C29—O20 | 124.6 (3) |
C1—C9—C4 | 116.7 (2) | O21—C29—C20 | 121.7 (3) |
O2—C10—O1 | 123.2 (3) | O20—C29—C20 | 113.6 (2) |
O2—C10—C1 | 122.1 (3) | C29—O20—H2O | 113.8 |
O1—C10—C1 | 114.6 (2) | C34—C30—C31 | 118.5 (3) |
C15—C11—C12 | 117.5 (3) | C34—C30—C22 | 121.9 (2) |
C15—C11—C3 | 122.4 (2) | C31—C30—C22 | 119.6 (2) |
C12—C11—C3 | 120.1 (2) | C32—C31—C30 | 119.3 (3) |
C13—C12—C11 | 119.7 (3) | C32—C31—H31 | 120.3 |
C13—C12—H12 | 120.2 | C30—C31—H31 | 120.3 |
C11—C12—H12 | 120.2 | N22—C32—C31 | 120.2 (3) |
N2—C13—C12 | 120.5 (3) | N22—C32—H32 | 119.9 |
N2—C13—H13 | 119.8 | C31—C32—H32 | 119.9 |
C12—C13—H13 | 119.8 | C33—N22—C32 | 122.6 (2) |
C14—N2—C13 | 122.0 (2) | C33—N22—H22N | 118.4 |
C14—N2—H2N | 123.0 | C32—N22—H22N | 119.1 |
C13—N2—H2N | 114.9 | N22—C33—C34 | 119.6 (3) |
N2—C14—C15 | 120.4 (3) | N22—C33—H33 | 120.2 |
N2—C14—H14 | 119.8 | C34—C33—H33 | 120.2 |
C15—C14—H14 | 119.8 | C33—C34—C30 | 119.8 (3) |
C14—C15—C11 | 119.9 (3) | C33—C34—H34 | 120.1 |
C14—C15—H15 | 120.1 | C30—C34—H34 | 120.1 |
C11—C15—H15 | 120.1 | H1W—O1W—H2W | 105.2 |
C21—C20—C28 | 119.3 (2) | H3W—O2W—H4W | 105.2 |
| | | |
C9—C1—C2—C3 | 1.1 (4) | C28—C20—C21—C22 | −2.8 (4) |
C10—C1—C2—C3 | −179.3 (2) | C29—C20—C21—C22 | 179.1 (2) |
C1—C2—C3—N1 | −0.7 (4) | C20—C21—C22—N21 | 2.2 (4) |
C1—C2—C3—C11 | 178.4 (2) | C20—C21—C22—C30 | −178.3 (2) |
C2—C3—N1—C4 | −0.7 (4) | C21—C22—N21—C23 | −0.1 (4) |
C11—C3—N1—C4 | −179.8 (2) | C30—C22—N21—C23 | −179.6 (2) |
C3—N1—C4—C5 | −177.9 (2) | C22—N21—C23—C24 | 178.6 (2) |
C3—N1—C4—C9 | 1.6 (4) | C22—N21—C23—C28 | −1.3 (4) |
N1—C4—C5—C6 | −179.9 (2) | N21—C23—C24—C25 | −177.7 (2) |
C9—C4—C5—C6 | 0.5 (4) | C28—C23—C24—C25 | 2.2 (4) |
C4—C5—C6—C7 | −0.1 (4) | C23—C24—C25—C26 | −0.8 (4) |
C5—C6—C7—C8 | −0.2 (4) | C24—C25—C26—C27 | −0.6 (4) |
C6—C7—C8—C9 | 0.0 (4) | C25—C26—C27—C28 | 0.5 (4) |
C7—C8—C9—C1 | −178.5 (3) | C26—C27—C28—C20 | 177.7 (3) |
C7—C8—C9—C4 | 0.4 (4) | C26—C27—C28—C23 | 0.9 (4) |
C2—C1—C9—C8 | 178.7 (3) | C21—C20—C28—C27 | −175.4 (3) |
C10—C1—C9—C8 | −0.8 (4) | C29—C20—C28—C27 | 2.5 (4) |
C2—C1—C9—C4 | −0.3 (4) | C21—C20—C28—C23 | 1.5 (4) |
C10—C1—C9—C4 | −179.8 (2) | C29—C20—C28—C23 | 179.4 (2) |
N1—C4—C9—C8 | 179.8 (2) | N21—C23—C28—C27 | 177.7 (2) |
C5—C4—C9—C8 | −0.7 (4) | C24—C23—C28—C27 | −2.2 (4) |
N1—C4—C9—C1 | −1.1 (4) | N21—C23—C28—C20 | 0.5 (4) |
C5—C4—C9—C1 | 178.4 (2) | C24—C23—C28—C20 | −179.3 (2) |
C2—C1—C10—O2 | −14.9 (4) | C21—C20—C29—O21 | 30.5 (4) |
C9—C1—C10—O2 | 164.6 (3) | C28—C20—C29—O21 | −147.4 (3) |
C2—C1—C10—O1 | 163.9 (2) | C21—C20—C29—O20 | −148.3 (2) |
C9—C1—C10—O1 | −16.5 (4) | C28—C20—C29—O20 | 33.8 (4) |
N1—C3—C11—C15 | −162.7 (3) | N21—C22—C30—C34 | −161.8 (3) |
C2—C3—C11—C15 | 18.2 (4) | C21—C22—C30—C34 | 18.7 (4) |
N1—C3—C11—C12 | 17.3 (4) | N21—C22—C30—C31 | 18.2 (4) |
C2—C3—C11—C12 | −161.8 (2) | C21—C22—C30—C31 | −161.3 (2) |
C15—C11—C12—C13 | −1.7 (4) | C34—C30—C31—C32 | −0.6 (4) |
C3—C11—C12—C13 | 178.3 (2) | C22—C30—C31—C32 | 179.4 (2) |
C11—C12—C13—N2 | −0.5 (4) | C30—C31—C32—N22 | −0.1 (4) |
C12—C13—N2—C14 | 2.0 (4) | C31—C32—N22—C33 | 0.2 (4) |
C13—N2—C14—C15 | −1.1 (4) | C32—N22—C33—C34 | 0.5 (4) |
N2—C14—C15—C11 | −1.1 (4) | N22—C33—C34—C30 | −1.3 (4) |
C12—C11—C15—C14 | 2.5 (4) | C31—C30—C34—C33 | 1.3 (4) |
C3—C11—C15—C14 | −177.5 (3) | C22—C30—C34—C33 | −178.7 (2) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.