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The preparation of coordination polymers (CPs) based on either transition metal centres or rare-earth cations has grown considerably in recent decades. The different coordination chemistry of these metals allied to the use of a large variety of organic linkers has led to an amazing structural diversity. Most of these compounds are based on carboxylic acids or nitrogen-containing ligands. More recently, a wide range of molecules containing phosphonic acid groups have been reported. For the particular case of Ca
2+-based CPs, some interesting functional materials have been reported. A novel one-dimensional Ca
2+-based coordination polymer with a new organic linker, namely poly[[diaqua[μ
4-(4,5-dicyano-1,2-phenylene)bis(phosphonato)][μ
3-(4,5-dicyano-1,2-phenylene)bis(phosphonato)]dicalcium(II)] tetrahydrate], {[Ca
2(C
8H
4N
2O
6P
2)
2(H
2O)
2]·4H
2O}
n, has been prepared at ambient temperature. The crystal structure features one-dimensional ladder-like
∞1[Ca
2(H
2cpp)
2(H
2O)
2] polymers [H
2cpp is (4,5-dicyano-1,2-phenylene)bis(phosphonate)], which are created by two distinct coordination modes of the anionic H
2cpp
2− cyanophosphonate organic linkers: while one molecule is only bound to Ca
2+ cations
via the phosphonate groups, the other establishes an extra single connection
via a cyano group. Ladders close pack with water molecules through an extensive network of strong and highly directional O—H
O and O—H
N hydrogen bonds; the observed donor–acceptor distances range from 2.499 (5) to 3.004 (6) Å and the interaction angles were found in the range 135–178°. One water molecule was found to be disordered over three distinct crystallographic positions. A detailed solution-state NMR study of the organic linker is also provided.
Supporting information
CCDC reference: 1496849
Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).
Poly[[diaqua[µ
4-(4,5-dicyano-1,2-phenylene)bis(phosphonato)][µ
3-(4,5-dicyano-1,2-phenylene)bis(phosphonato)]dicalcium(II)] tetrahydrate]
top
Crystal data top
[Ca2(C8H4N2O6P2)2(H2O)2]·4H2O | F(000) = 1552 |
Mr = 760.40 | Dx = 1.746 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.4384 (11) Å | Cell parameters from 9894 reflections |
b = 25.2929 (18) Å | θ = 2.5–27.5° |
c = 6.9599 (5) Å | µ = 0.70 mm−1 |
β = 91.493 (3)° | T = 180 K |
V = 2892.8 (4) Å3 | Needle, colourless |
Z = 4 | 0.10 × 0.06 × 0.01 mm |
Data collection top
Bruker D8 QUEST diffractometer | 5266 independent reflections |
Radiation source: Sealed tube | 4050 reflections with I > 2σ(I) |
Multi-layer X-ray mirror monochromator | Rint = 0.065 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 25.3°, θmin = 3.6° |
ω / φ scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | k = −30→30 |
Tmin = 0.665, Tmax = 0.746 | l = −8→6 |
27705 measured reflections | |
Refinement top
Refinement on F2 | 17 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0456P)2 + 10.5068P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
5266 reflections | Δρmax = 1.11 e Å−3 |
437 parameters | Δρmin = −0.46 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 | Occ. (<1) |
Ca1 | 0.21357 (5) | 0.48752 (4) | 0.48298 (12) | 0.0121 (2) | |
O1W | 0.1289 (2) | 0.41194 (14) | 0.4757 (5) | 0.0283 (9) | |
H1X | 0.083 (2) | 0.4128 (18) | 0.556 (7) | 0.042* | |
H1Y | 0.149 (3) | 0.3768 (8) | 0.467 (8) | 0.042* | |
Ca2 | 0.26293 (5) | 0.55449 (4) | −0.01741 (12) | 0.0129 (2) | |
O2W | 0.3849 (2) | 0.60987 (14) | 0.0272 (5) | 0.0251 (8) | |
H2X | 0.416 (3) | 0.605 (2) | −0.084 (4) | 0.038* | |
H2Y | 0.414 (3) | 0.597 (2) | 0.137 (4) | 0.038* | |
P1 | 0.07803 (7) | 0.57959 (5) | 0.28875 (17) | 0.0137 (3) | |
P2 | 0.27497 (7) | 0.60345 (5) | 0.47447 (16) | 0.0123 (3) | |
P3 | 0.19620 (7) | 0.44154 (5) | 0.98306 (16) | 0.0127 (3) | |
P4 | 0.38005 (7) | 0.44944 (5) | 0.76973 (16) | 0.0133 (3) | |
O1 | 0.10166 (18) | 0.54102 (12) | 0.4433 (4) | 0.0163 (7) | |
O2 | 0.11751 (18) | 0.56490 (13) | 0.0942 (4) | 0.0159 (7) | |
H2 | 0.081 (2) | 0.560 (2) | −0.012 (5) | 0.024* | |
O3 | −0.01218 (18) | 0.58811 (13) | 0.2597 (4) | 0.0177 (7) | |
O4 | 0.27202 (18) | 0.56479 (12) | 0.3114 (4) | 0.0156 (7) | |
O5 | 0.26030 (19) | 0.57702 (13) | 0.6615 (4) | 0.0183 (7) | |
O6 | 0.35591 (19) | 0.63571 (13) | 0.4760 (5) | 0.0236 (8) | |
H6 | 0.3892 | 0.6223 | 0.5558 | 0.035* | |
O7 | 0.19488 (18) | 0.47961 (12) | 0.8170 (4) | 0.0137 (7) | |
O8 | 0.11072 (19) | 0.41838 (13) | 1.0214 (4) | 0.0185 (7) | |
H8 | 0.0848 | 0.4147 | 0.9166 | 0.028* | |
O9 | 0.23133 (18) | 0.46456 (12) | 1.1642 (4) | 0.0153 (7) | |
O10 | 0.34371 (18) | 0.46164 (13) | 0.5742 (4) | 0.0161 (7) | |
O11 | 0.36883 (18) | 0.49098 (12) | 0.9206 (4) | 0.0150 (7) | |
O12 | 0.47252 (18) | 0.43474 (13) | 0.7524 (5) | 0.0195 (7) | |
H12 | 0.4995 | 0.4622 | 0.7312 | 0.029* | |
N1 | 0.2182 (3) | 0.84492 (17) | 0.4633 (6) | 0.0232 (9) | |
N2 | −0.0175 (4) | 0.8114 (2) | 0.3213 (10) | 0.0628 (18) | |
N3 | 0.4199 (3) | 0.2033 (2) | 0.8105 (8) | 0.0445 (13) | |
N4 | 0.1946 (4) | 0.1987 (2) | 0.9551 (8) | 0.0480 (14) | |
C1 | 0.1198 (3) | 0.64455 (18) | 0.3556 (6) | 0.0145 (9) | |
C2 | 0.1994 (3) | 0.65507 (18) | 0.4251 (6) | 0.0141 (9) | |
C3 | 0.2237 (3) | 0.70717 (18) | 0.4555 (6) | 0.0174 (10) | |
H3 | 0.2778 | 0.7144 | 0.4992 | 0.021* | |
C4 | 0.1697 (3) | 0.74911 (19) | 0.4227 (6) | 0.0199 (10) | |
C5 | 0.0894 (3) | 0.73801 (19) | 0.3647 (7) | 0.0209 (11) | |
C6 | 0.0661 (3) | 0.68640 (19) | 0.3304 (7) | 0.0192 (10) | |
H6A | 0.0118 | 0.6793 | 0.2884 | 0.023* | |
C7 | 0.1968 (3) | 0.8027 (2) | 0.4459 (7) | 0.0243 (11) | |
C8 | 0.0308 (4) | 0.7803 (2) | 0.3392 (8) | 0.0324 (13) | |
C9 | 0.3783 (3) | 0.34030 (19) | 0.8153 (7) | 0.0198 (10) | |
H9 | 0.4320 | 0.3420 | 0.7684 | 0.024* | |
C10 | 0.2573 (3) | 0.38361 (18) | 0.9209 (6) | 0.0132 (9) | |
C11 | 0.3358 (3) | 0.38678 (18) | 0.8459 (6) | 0.0156 (10) | |
C12 | 0.3442 (3) | 0.2914 (2) | 0.8519 (7) | 0.0225 (11) | |
C13 | 0.2651 (3) | 0.28838 (19) | 0.9180 (7) | 0.0221 (11) | |
C14 | 0.2224 (3) | 0.33432 (19) | 0.9546 (7) | 0.0191 (10) | |
H14 | 0.1690 | 0.3323 | 1.0030 | 0.023* | |
C15 | 0.3892 (3) | 0.2431 (2) | 0.8245 (8) | 0.0297 (12) | |
C16 | 0.2254 (3) | 0.2379 (2) | 0.9432 (8) | 0.0275 (12) | |
O3W | 0.43889 (19) | 0.48070 (14) | 1.2731 (5) | 0.0200 (7) | |
H3X | 0.411 (2) | 0.481 (2) | 1.152 (3) | 0.030* | |
H3Y | 0.401 (2) | 0.479 (2) | 1.373 (4) | 0.030* | |
O4W | 0.0320 (3) | 0.5554 (3) | −0.2061 (6) | 0.073 (2) | |
H4X | 0.051 (4) | 0.546 (4) | −0.328 (5) | 0.109* | |
H4Y | −0.0246 (12) | 0.562 (4) | −0.213 (10) | 0.109* | |
O5W | 0.4773 (2) | 0.61236 (15) | 0.7077 (5) | 0.0267 (8) | |
H5X | 0.502 (3) | 0.5783 (8) | 0.711 (9) | 0.040* | |
H5Y | 0.519 (2) | 0.6385 (12) | 0.706 (8) | 0.040* | |
O6W | 0.4021 (8) | 0.7237 (5) | 0.106 (2) | 0.055 (2)* | 0.375 (8) |
O7W | 0.4377 (11) | 0.7206 (7) | 0.296 (3) | 0.055 (2)* | 0.262 (8) |
O8W | 0.3948 (8) | 0.7254 (5) | −0.046 (2) | 0.055 (2)* | 0.363 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.0123 (4) | 0.0148 (5) | 0.0091 (4) | 0.0004 (4) | 0.0009 (3) | 0.0008 (4) |
O1W | 0.034 (2) | 0.022 (2) | 0.030 (2) | −0.0097 (16) | 0.0191 (16) | −0.0055 (16) |
Ca2 | 0.0161 (5) | 0.0137 (5) | 0.0090 (4) | 0.0008 (4) | 0.0002 (3) | −0.0001 (4) |
O2W | 0.0251 (19) | 0.028 (2) | 0.0225 (18) | −0.0025 (16) | −0.0002 (15) | 0.0023 (16) |
P1 | 0.0114 (6) | 0.0153 (6) | 0.0143 (6) | 0.0002 (5) | 0.0008 (4) | −0.0004 (5) |
P2 | 0.0145 (6) | 0.0125 (6) | 0.0098 (5) | −0.0017 (5) | −0.0009 (4) | 0.0003 (5) |
P3 | 0.0131 (6) | 0.0150 (6) | 0.0100 (5) | −0.0017 (5) | 0.0015 (4) | 0.0006 (5) |
P4 | 0.0120 (6) | 0.0153 (6) | 0.0127 (5) | 0.0006 (5) | 0.0007 (4) | 0.0003 (5) |
O1 | 0.0146 (16) | 0.0156 (17) | 0.0188 (16) | 0.0004 (13) | 0.0005 (13) | 0.0027 (13) |
O2 | 0.0138 (16) | 0.0210 (18) | 0.0129 (15) | −0.0006 (13) | −0.0001 (12) | −0.0028 (13) |
O3 | 0.0132 (16) | 0.0242 (19) | 0.0158 (16) | 0.0008 (14) | 0.0002 (13) | −0.0004 (14) |
O4 | 0.0192 (17) | 0.0173 (17) | 0.0103 (15) | 0.0012 (13) | 0.0013 (13) | −0.0008 (13) |
O5 | 0.0252 (18) | 0.0179 (18) | 0.0120 (15) | 0.0010 (14) | 0.0013 (13) | 0.0018 (13) |
O6 | 0.0158 (17) | 0.0222 (19) | 0.032 (2) | −0.0029 (14) | −0.0074 (15) | 0.0064 (16) |
O7 | 0.0141 (16) | 0.0139 (17) | 0.0132 (15) | 0.0000 (12) | 0.0018 (12) | 0.0000 (13) |
O8 | 0.0144 (16) | 0.0270 (19) | 0.0141 (16) | −0.0046 (14) | 0.0009 (13) | 0.0006 (15) |
O9 | 0.0160 (16) | 0.0183 (17) | 0.0118 (15) | −0.0017 (13) | 0.0016 (12) | −0.0006 (13) |
O10 | 0.0144 (16) | 0.0226 (18) | 0.0115 (15) | 0.0009 (13) | 0.0028 (12) | 0.0010 (13) |
O11 | 0.0119 (15) | 0.0172 (17) | 0.0158 (16) | 0.0006 (13) | 0.0005 (12) | −0.0012 (13) |
O12 | 0.0135 (16) | 0.0217 (19) | 0.0235 (18) | 0.0022 (13) | 0.0013 (14) | −0.0011 (15) |
N1 | 0.031 (2) | 0.018 (2) | 0.021 (2) | −0.0016 (19) | 0.0066 (18) | −0.0019 (18) |
N2 | 0.053 (4) | 0.043 (4) | 0.092 (5) | 0.023 (3) | −0.013 (3) | −0.016 (3) |
N3 | 0.048 (3) | 0.023 (3) | 0.062 (4) | 0.013 (2) | −0.002 (3) | −0.005 (3) |
N4 | 0.061 (4) | 0.030 (3) | 0.053 (3) | −0.012 (3) | −0.007 (3) | 0.005 (3) |
C1 | 0.019 (2) | 0.014 (2) | 0.010 (2) | −0.0018 (19) | 0.0021 (18) | −0.0012 (18) |
C2 | 0.019 (2) | 0.018 (2) | 0.006 (2) | −0.0012 (19) | 0.0037 (17) | 0.0014 (18) |
C3 | 0.024 (3) | 0.017 (2) | 0.012 (2) | −0.004 (2) | 0.0039 (19) | 0.0016 (19) |
C4 | 0.034 (3) | 0.014 (2) | 0.012 (2) | −0.002 (2) | 0.004 (2) | −0.0014 (19) |
C5 | 0.026 (3) | 0.021 (3) | 0.016 (2) | 0.008 (2) | 0.003 (2) | 0.001 (2) |
C6 | 0.019 (2) | 0.021 (3) | 0.017 (2) | 0.001 (2) | −0.0007 (19) | 0.001 (2) |
C7 | 0.035 (3) | 0.024 (3) | 0.014 (2) | 0.004 (2) | 0.006 (2) | −0.001 (2) |
C8 | 0.038 (3) | 0.021 (3) | 0.038 (3) | 0.009 (3) | −0.004 (3) | −0.005 (2) |
C9 | 0.023 (3) | 0.020 (3) | 0.016 (2) | 0.003 (2) | −0.0018 (19) | 0.000 (2) |
C10 | 0.019 (2) | 0.012 (2) | 0.008 (2) | 0.0015 (18) | −0.0020 (17) | 0.0001 (17) |
C11 | 0.016 (2) | 0.018 (3) | 0.013 (2) | 0.0002 (19) | −0.0016 (18) | −0.0023 (19) |
C12 | 0.029 (3) | 0.018 (3) | 0.020 (2) | 0.006 (2) | −0.001 (2) | 0.001 (2) |
C13 | 0.030 (3) | 0.017 (3) | 0.020 (2) | −0.002 (2) | −0.003 (2) | 0.003 (2) |
C14 | 0.022 (3) | 0.018 (3) | 0.017 (2) | −0.003 (2) | 0.0001 (19) | −0.001 (2) |
C15 | 0.036 (3) | 0.022 (3) | 0.030 (3) | 0.002 (2) | −0.005 (2) | −0.002 (2) |
C16 | 0.032 (3) | 0.021 (3) | 0.029 (3) | −0.003 (2) | −0.005 (2) | 0.001 (2) |
O3W | 0.0147 (17) | 0.030 (2) | 0.0157 (16) | 0.0005 (14) | 0.0019 (13) | 0.0027 (15) |
O4W | 0.024 (2) | 0.173 (6) | 0.021 (2) | 0.030 (3) | −0.0032 (17) | −0.023 (3) |
O5W | 0.0198 (19) | 0.025 (2) | 0.035 (2) | −0.0024 (15) | −0.0017 (16) | 0.0026 (17) |
Geometric parameters (Å, º) top
Ca1—O1 | 2.294 (3) | O6—H6 | 0.8400 |
Ca1—O4 | 2.496 (3) | O7—Ca2ii | 2.470 (3) |
Ca1—O5 | 2.685 (3) | O8—H8 | 0.8400 |
Ca1—O7 | 2.362 (3) | O9—Ca1ii | 2.319 (3) |
Ca1—O9i | 2.319 (3) | O9—Ca2ii | 2.660 (3) |
Ca1—O10 | 2.310 (3) | O11—Ca2ii | 2.416 (3) |
Ca1—O1W | 2.365 (3) | O12—H12 | 0.8400 |
Ca1—Ca2ii | 3.9334 (12) | N1—C7 | 1.130 (6) |
Ca1—Ca2 | 3.9753 (12) | N1—Ca2iv | 2.651 (4) |
O1W—H1X | 0.947 (10) | N2—C8 | 1.122 (7) |
O1W—H1Y | 0.949 (10) | N3—C15 | 1.130 (7) |
Ca2—O2 | 2.546 (3) | N4—C16 | 1.117 (7) |
Ca2—O4 | 2.304 (3) | C1—C6 | 1.386 (7) |
Ca2—O5i | 2.306 (3) | C1—C2 | 1.409 (6) |
Ca2—O7i | 2.469 (3) | C2—C3 | 1.392 (6) |
Ca2—O9i | 2.660 (3) | C3—C4 | 1.399 (7) |
Ca2—O11i | 2.416 (3) | C3—H3 | 0.9500 |
Ca2—N1iii | 2.651 (4) | C4—C5 | 1.398 (7) |
Ca2—O2W | 2.459 (4) | C4—C7 | 1.434 (7) |
O2W—H2X | 0.948 (10) | C5—C6 | 1.379 (7) |
O2W—H2Y | 0.946 (10) | C5—C8 | 1.449 (7) |
P1—O1 | 1.496 (3) | C6—H6A | 0.9500 |
P1—O3 | 1.507 (3) | C9—C12 | 1.384 (7) |
P1—O2 | 1.562 (3) | C9—C11 | 1.388 (7) |
P1—C1 | 1.836 (5) | C9—H9 | 0.9500 |
P2—O5 | 1.489 (3) | C10—C14 | 1.395 (6) |
P2—O4 | 1.498 (3) | C10—C11 | 1.406 (6) |
P2—O6 | 1.561 (3) | C12—C13 | 1.392 (7) |
P2—C2 | 1.828 (5) | C12—C15 | 1.445 (7) |
P3—O9 | 1.492 (3) | C13—C14 | 1.385 (7) |
P3—O7 | 1.504 (3) | C13—C16 | 1.448 (7) |
P3—O8 | 1.552 (3) | C14—H14 | 0.9500 |
P3—C10 | 1.834 (5) | O3W—H3X | 0.946 (10) |
P3—Ca2ii | 3.0603 (15) | O3W—H3Y | 0.945 (10) |
P4—O11 | 1.500 (3) | O4W—H4X | 0.946 (10) |
P4—O10 | 1.504 (3) | O4W—H4Y | 0.945 (10) |
P4—O12 | 1.573 (3) | O5W—H5X | 0.949 (10) |
P4—C11 | 1.828 (5) | O5W—H5Y | 0.949 (10) |
O2—H2 | 0.947 (10) | O6W—O8W | 1.061 (16) |
O5—Ca2ii | 2.306 (3) | O6W—O7W | 1.44 (2) |
| | | |
O1—Ca1—O4 | 78.35 (11) | O9—P3—Ca2ii | 60.36 (13) |
O1—Ca1—O5 | 77.14 (11) | O7—P3—Ca2ii | 53.09 (12) |
O1—Ca1—O7 | 92.53 (11) | O8—P3—Ca2ii | 132.75 (14) |
O1—Ca1—O9i | 98.80 (11) | C10—P3—Ca2ii | 123.16 (15) |
O1—Ca1—O10 | 159.06 (12) | O11—P4—O10 | 115.88 (18) |
O1—Ca1—O1W | 90.25 (13) | O11—P4—O12 | 110.84 (18) |
O4—Ca1—O5 | 56.78 (9) | O10—P4—O12 | 109.95 (18) |
O7—Ca1—O4 | 126.80 (11) | O11—P4—C11 | 110.31 (19) |
O7—Ca1—O5 | 70.05 (10) | O10—P4—C11 | 106.76 (19) |
O7—Ca1—O1W | 82.00 (12) | O12—P4—C11 | 102.1 (2) |
O9i—Ca1—O4 | 71.26 (11) | O11—P4—Ca1 | 95.65 (12) |
O9i—Ca1—O5 | 127.75 (11) | O12—P4—Ca1 | 140.23 (13) |
O9i—Ca1—O7 | 160.64 (12) | C11—P4—Ca1 | 95.34 (15) |
O9i—Ca1—O1W | 82.29 (12) | P1—O1—Ca1 | 131.58 (18) |
O10—Ca1—O4 | 89.32 (11) | P1—O2—Ca2 | 134.73 (17) |
O10—Ca1—O5 | 81.95 (11) | P1—O2—H2 | 116 (3) |
O10—Ca1—O7 | 81.29 (10) | Ca2—O2—H2 | 110 (3) |
O10—Ca1—O9i | 93.05 (11) | P2—O4—Ca2 | 145.71 (19) |
O10—Ca1—O1W | 108.50 (13) | P2—O4—Ca1 | 98.86 (15) |
O1W—Ca1—O4 | 148.95 (12) | Ca2—O4—Ca1 | 111.77 (13) |
O1W—Ca1—O5 | 148.50 (11) | P2—O5—Ca2ii | 163.6 (2) |
Ca1—O1W—H1X | 116 (3) | P2—O5—Ca1 | 91.42 (15) |
Ca1—O1W—H1Y | 124 (3) | Ca2ii—O5—Ca1 | 103.77 (12) |
H1X—O1W—H1Y | 109.7 (16) | P2—O6—H6 | 109.5 |
O2—Ca2—O9i | 75.34 (10) | P3—O7—Ca1 | 144.20 (18) |
O2—Ca2—N1iii | 69.80 (12) | P3—O7—Ca2ii | 97.78 (15) |
O4—Ca2—O2 | 73.89 (10) | Ca1—O7—Ca2ii | 108.99 (12) |
O4—Ca2—O5i | 159.04 (12) | P3—O8—H8 | 109.5 |
O4—Ca2—O7i | 124.54 (11) | P3—O9—Ca1ii | 148.31 (19) |
O4—Ca2—O9i | 68.47 (10) | P3—O9—Ca2ii | 90.47 (14) |
O4—Ca2—O11i | 102.96 (11) | Ca1ii—O9—Ca2ii | 105.75 (12) |
O4—Ca2—N1iii | 87.27 (12) | P4—O10—Ca1 | 130.54 (17) |
O4—Ca2—O2W | 77.21 (12) | P4—O11—Ca2ii | 133.87 (17) |
O5i—Ca2—O2 | 106.02 (11) | P4—O12—H12 | 109.5 |
O5i—Ca2—O7i | 74.96 (11) | C7—N1—Ca2iv | 176.2 (4) |
O5i—Ca2—O9i | 132.30 (11) | C6—C1—C2 | 118.8 (4) |
O5i—Ca2—O11i | 89.23 (11) | C6—C1—P1 | 114.8 (3) |
O5i—Ca2—N1iii | 73.48 (12) | C2—C1—P1 | 126.4 (4) |
O5i—Ca2—O2W | 88.64 (12) | C3—C2—C1 | 119.4 (4) |
O7i—Ca2—O2 | 78.71 (10) | C3—C2—P2 | 117.2 (3) |
O7i—Ca2—O9i | 58.29 (10) | C1—C2—P2 | 123.4 (4) |
O7i—Ca2—N1iii | 126.21 (12) | C2—C3—C4 | 121.0 (4) |
O11i—Ca2—O2 | 144.08 (11) | C2—C3—H3 | 119.5 |
O11i—Ca2—O7i | 74.13 (10) | C4—C3—H3 | 119.5 |
O11i—Ca2—O9i | 70.54 (10) | C5—C4—C3 | 119.1 (4) |
O11i—Ca2—N1iii | 146.04 (12) | C5—C4—C7 | 120.7 (5) |
O11i—Ca2—O2W | 79.17 (11) | C3—C4—C7 | 120.2 (5) |
O2W—Ca2—O2 | 132.19 (11) | C6—C5—C4 | 119.7 (4) |
O2W—Ca2—O7i | 148.61 (11) | C6—C5—C8 | 119.8 (5) |
O2W—Ca2—O9i | 126.56 (11) | C4—C5—C8 | 120.5 (5) |
O2W—Ca2—N1iii | 71.58 (13) | C5—C6—C1 | 121.9 (4) |
N1iii—Ca2—O9i | 141.94 (11) | C5—C6—H6A | 119.1 |
Ca2—O2W—H2X | 106 (3) | C1—C6—H6A | 119.1 |
Ca2—O2W—H2Y | 107 (3) | N1—C7—C4 | 179.7 (6) |
H2X—O2W—H2Y | 109.9 (16) | N2—C8—C5 | 176.7 (7) |
O1—P1—O3 | 115.22 (18) | C12—C9—C11 | 121.3 (5) |
O1—P1—O2 | 111.24 (18) | C12—C9—H9 | 119.4 |
O3—P1—O2 | 110.33 (17) | C11—C9—H9 | 119.4 |
O1—P1—C1 | 108.25 (19) | C14—C10—C11 | 119.9 (4) |
O3—P1—C1 | 105.4 (2) | C14—C10—P3 | 116.4 (3) |
O2—P1—C1 | 105.74 (19) | C11—C10—P3 | 123.7 (3) |
O3—P1—Ca1 | 140.12 (14) | C9—C11—C10 | 118.7 (4) |
O2—P1—Ca1 | 84.33 (12) | C9—C11—P4 | 118.9 (4) |
C1—P1—Ca1 | 105.64 (15) | C10—C11—P4 | 122.2 (3) |
O5—P2—O4 | 111.50 (18) | C9—C12—C13 | 119.8 (5) |
O5—P2—O6 | 112.72 (19) | C9—C12—C15 | 121.3 (5) |
O4—P2—O6 | 110.94 (19) | C13—C12—C15 | 118.9 (5) |
O5—P2—C2 | 111.11 (19) | C14—C13—C12 | 119.7 (5) |
O4—P2—C2 | 108.38 (19) | C14—C13—C16 | 119.1 (5) |
O6—P2—C2 | 101.7 (2) | C12—C13—C16 | 121.1 (5) |
O5—P2—Ca1 | 59.91 (13) | C13—C14—C10 | 120.4 (5) |
O4—P2—Ca1 | 52.64 (12) | C13—C14—H14 | 119.8 |
O6—P2—Ca1 | 140.52 (14) | C10—C14—H14 | 119.8 |
C2—P2—Ca1 | 117.31 (15) | N3—C15—C12 | 174.7 (6) |
O9—P3—O7 | 113.39 (18) | N4—C16—C13 | 177.3 (6) |
O9—P3—O8 | 109.54 (18) | H3X—O3W—H3Y | 110.3 (16) |
O7—P3—O8 | 112.27 (18) | H4X—O4W—H4Y | 110.4 (17) |
O9—P3—C10 | 107.99 (19) | H5X—O5W—H5Y | 109.4 (16) |
O7—P3—C10 | 109.11 (18) | O8W—O6W—O7W | 162.5 (16) |
O8—P3—C10 | 104.0 (2) | | |
| | | |
O3—P1—O1—Ca1 | 152.6 (2) | P1—C1—C2—P2 | −3.6 (6) |
O2—P1—O1—Ca1 | 26.1 (3) | O5—P2—C2—C3 | 102.5 (4) |
C1—P1—O1—Ca1 | −89.7 (3) | O4—P2—C2—C3 | −134.6 (3) |
O1—P1—O2—Ca2 | −60.0 (3) | O6—P2—C2—C3 | −17.6 (4) |
O3—P1—O2—Ca2 | 170.9 (2) | Ca1—P2—C2—C3 | 168.6 (3) |
C1—P1—O2—Ca2 | 57.3 (3) | O5—P2—C2—C1 | −78.7 (4) |
Ca1—P1—O2—Ca2 | −47.3 (2) | O4—P2—C2—C1 | 44.2 (4) |
O5—P2—O4—Ca2 | 165.4 (3) | O6—P2—C2—C1 | 161.1 (4) |
O6—P2—O4—Ca2 | −68.1 (4) | Ca1—P2—C2—C1 | −12.6 (4) |
C2—P2—O4—Ca2 | 42.7 (4) | C1—C2—C3—C4 | 1.6 (6) |
Ca1—P2—O4—Ca2 | 153.5 (4) | P2—C2—C3—C4 | −179.5 (3) |
O5—P2—O4—Ca1 | 11.8 (2) | C2—C3—C4—C5 | 2.1 (7) |
O6—P2—O4—Ca1 | 138.38 (16) | C2—C3—C4—C7 | −177.0 (4) |
C2—P2—O4—Ca1 | −110.76 (17) | C3—C4—C5—C6 | −3.6 (7) |
O4—P2—O5—Ca2ii | 147.1 (7) | C7—C4—C5—C6 | 175.5 (4) |
O6—P2—O5—Ca2ii | 21.6 (8) | C3—C4—C5—C8 | 176.8 (5) |
C2—P2—O5—Ca2ii | −91.9 (7) | C7—C4—C5—C8 | −4.1 (7) |
Ca1—P2—O5—Ca2ii | 158.0 (8) | C4—C5—C6—C1 | 1.3 (7) |
O4—P2—O5—Ca1 | −10.87 (19) | C8—C5—C6—C1 | −179.0 (5) |
O6—P2—O5—Ca1 | −136.43 (16) | C2—C1—C6—C5 | 2.5 (7) |
C2—P2—O5—Ca1 | 110.16 (18) | P1—C1—C6—C5 | −176.6 (4) |
O9—P3—O7—Ca1 | 141.4 (3) | O9—P3—C10—C14 | 105.1 (4) |
O8—P3—O7—Ca1 | −93.8 (3) | O7—P3—C10—C14 | −131.3 (3) |
C10—P3—O7—Ca1 | 21.0 (4) | O8—P3—C10—C14 | −11.3 (4) |
Ca2ii—P3—O7—Ca1 | 138.7 (3) | Ca2ii—P3—C10—C14 | 170.9 (3) |
O9—P3—O7—Ca2ii | 2.8 (2) | O9—P3—C10—C11 | −74.0 (4) |
O8—P3—O7—Ca2ii | 127.57 (16) | O7—P3—C10—C11 | 49.7 (4) |
C10—P3—O7—Ca2ii | −117.63 (17) | O8—P3—C10—C11 | 169.7 (4) |
O7—P3—O9—Ca1ii | 119.5 (4) | Ca2ii—P3—C10—C11 | −8.1 (4) |
O8—P3—O9—Ca1ii | −6.8 (4) | C12—C9—C11—C10 | 1.9 (7) |
C10—P3—O9—Ca1ii | −119.5 (4) | C12—C9—C11—P4 | −173.3 (4) |
Ca2ii—P3—O9—Ca1ii | 122.0 (4) | C14—C10—C11—C9 | −3.0 (6) |
O7—P3—O9—Ca2ii | −2.54 (18) | P3—C10—C11—C9 | 176.1 (3) |
O8—P3—O9—Ca2ii | −128.81 (16) | C14—C10—C11—P4 | 172.1 (3) |
C10—P3—O9—Ca2ii | 118.48 (17) | P3—C10—C11—P4 | −8.9 (5) |
O11—P4—O10—Ca1 | −52.1 (3) | O11—P4—C11—C9 | −137.4 (4) |
O12—P4—O10—Ca1 | −178.8 (2) | O10—P4—C11—C9 | 95.9 (4) |
C11—P4—O10—Ca1 | 71.2 (3) | O12—P4—C11—C9 | −19.6 (4) |
O10—P4—O11—Ca2ii | 32.3 (3) | Ca1—P4—C11—C9 | 124.5 (4) |
O12—P4—O11—Ca2ii | 158.5 (2) | O11—P4—C11—C10 | 47.5 (4) |
C11—P4—O11—Ca2ii | −89.1 (3) | O10—P4—C11—C10 | −79.2 (4) |
Ca1—P4—O11—Ca2ii | 8.7 (2) | O12—P4—C11—C10 | 165.4 (4) |
O1—P1—C1—C6 | −135.0 (3) | Ca1—P4—C11—C10 | −50.5 (4) |
O3—P1—C1—C6 | −11.2 (4) | C11—C9—C12—C13 | 0.9 (7) |
O2—P1—C1—C6 | 105.7 (3) | C11—C9—C12—C15 | −178.5 (5) |
Ca1—P1—C1—C6 | −165.9 (3) | C9—C12—C13—C14 | −2.8 (7) |
O1—P1—C1—C2 | 45.9 (4) | C15—C12—C13—C14 | 176.7 (5) |
O3—P1—C1—C2 | 169.7 (4) | C9—C12—C13—C16 | 175.1 (5) |
O2—P1—C1—C2 | −73.4 (4) | C15—C12—C13—C16 | −5.5 (7) |
Ca1—P1—C1—C2 | 15.0 (4) | C12—C13—C14—C10 | 1.7 (7) |
C6—C1—C2—C3 | −3.9 (6) | C16—C13—C14—C10 | −176.2 (4) |
P1—C1—C2—C3 | 175.1 (3) | C11—C10—C14—C13 | 1.2 (7) |
C6—C1—C2—P2 | 177.3 (3) | P3—C10—C14—C13 | −177.9 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1X···O3v | 0.95 | 1.76 | 2.693 (4) | 169 |
O1W—H1Y···N4vi | 0.95 | 2.06 | 3.004 (6) | 178 |
O2W—H2X···O5Wi | 0.95 | 1.79 | 2.725 (5) | 167 |
O2W—H2Y···O12vii | 0.95 | 2.16 | 2.988 (5) | 146 |
O3W—H3X···O11 | 0.95 | 1.76 | 2.696 (4) | 171 |
O3W—H3Y···O10ii | 0.95 | 1.77 | 2.691 (4) | 166 |
O4W—H4X···O1i | 0.95 | 1.82 | 2.747 (5) | 167 |
O4W—H4Y···O8v | 0.95 | 2.04 | 2.785 (5) | 135 |
O5W—H5X···O3Wviii | 0.95 | 1.79 | 2.729 (5) | 171 |
O5W—H5Y···N3ix | 0.95 | 1.93 | 2.860 (6) | 166 |
O2—H2···O4W | 0.95 | 1.56 | 2.499 (5) | 171 |
O6—H6···O5W | 0.84 | 1.79 | 2.600 (5) | 162 |
O8—H8···O3v | 0.84 | 1.69 | 2.513 (4) | 165 |
O12—H12···O3Wviii | 0.84 | 1.76 | 2.596 (5) | 171 |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (v) −x, −y+1, −z+1; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+1, −z+2; (ix) −x+1, y+1/2, −z+3/2. |
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