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The reaction of Cu(NO
3)
2·3H
2O with 2,4′-oxybis(benzoic acid) and 4,4′-bipyridine under hydrothermal conditions produced a new mixed-ligand two-dimensional copper(II) coordination polymer, namely poly[[(μ-4,4′-bipyridine-κ
2N,
N′)[μ-2,4′-oxybis(benzoato)-κ
4O2,
O2′:
O4,
O4′]copper(II)] monohydrate], {[Cu(C
14H
8O
5)(C
10H
8N
2)]·H
2O}
n, which was characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis and single-crystal X-ray diffraction. The X-ray diffraction crystal structure analysis reveals that the Cu
II ions are connected to form a two-dimensional wave-like network through 4,4′-bipyridine and 2,4′-oxybis(benzoate) ligands. The two-dimensional layers are expanded into a three-dimensional supramolecular structure through intermolecular O—H
O and C—H
O hydrogen bonds. Furthermore, magnetic susceptibility measurements indicate that the complex shows weak antiferromagnetic interactions between adjacent Cu
II ions.
Supporting information
CCDC reference: 1534325
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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[[(µ-4,4'-bipyridine-
κ2N,
N')(µ-2,4'-oxydibenzoato-
κ4O2,
O2':
O4,
O4')copper(II)]
monohydrate]{[Cu(C
14H
8O
5)(C
10H
8N
2)]·H
2O
top
Crystal data top
[Cu(C14H8O5)(C10H8N2)]·H2O | F(000) = 1012 |
Mr = 493.94 | Dx = 1.510 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.731 (4) Å | Cell parameters from 2152 reflections |
b = 14.274 (5) Å | θ = 2.3–23.7° |
c = 13.211 (5) Å | µ = 1.05 mm−1 |
β = 100.862 (7)° | T = 296 K |
V = 2172.6 (14) Å3 | Block, blue |
Z = 4 | 0.34 × 0.25 × 0.21 mm |
Data collection top
Bruker SMART diffractometer | 2612 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→9 |
Tmin = 0.737, Tmax = 0.802 | k = −16→14 |
10779 measured reflections | l = −14→15 |
3821 independent reflections | |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3821 reflections | Δρmax = 0.50 e Å−3 |
302 parameters | Δρmin = −0.33 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) |
Cu1 | 0.16833 (3) | 0.25361 (3) | 0.81160 (3) | 0.03615 (15) | |
O1 | 0.2541 (2) | 0.36943 (15) | 0.85492 (19) | 0.0445 (6) | |
O2 | 0.3035 (3) | 0.3459 (2) | 0.7048 (2) | 0.0777 (9) | |
O3 | 0.52529 (19) | 0.41323 (16) | 0.89850 (19) | 0.0487 (6) | |
O4 | 1.01783 (19) | 0.32147 (16) | 0.78438 (19) | 0.0464 (6) | |
O5 | 1.0173 (2) | 0.22406 (17) | 0.91366 (19) | 0.0492 (6) | |
N1 | 0.2914 (2) | 0.16870 (18) | 0.8878 (2) | 0.0389 (7) | |
N2 | 0.1073 (2) | 0.15638 (17) | 0.7053 (2) | 0.0347 (6) | |
C1 | 0.3033 (3) | 0.3943 (2) | 0.7809 (3) | 0.0402 (8) | |
C2 | 0.3640 (3) | 0.4872 (2) | 0.7944 (3) | 0.0368 (8) | |
C3 | 0.3108 (3) | 0.5690 (2) | 0.7508 (3) | 0.0526 (10) | |
H3 | 0.2369 | 0.5661 | 0.7103 | 0.063* | |
C4 | 0.3677 (4) | 0.6545 (3) | 0.7675 (3) | 0.0630 (12) | |
H4 | 0.3315 | 0.7087 | 0.7383 | 0.076* | |
C5 | 0.4771 (4) | 0.6597 (3) | 0.8270 (4) | 0.0626 (12) | |
H5 | 0.5144 | 0.7173 | 0.8378 | 0.075* | |
C6 | 0.5317 (3) | 0.5800 (3) | 0.8707 (3) | 0.0528 (10) | |
H6A | 0.6053 | 0.5835 | 0.9116 | 0.063* | |
C7 | 0.4754 (3) | 0.4951 (2) | 0.8528 (3) | 0.0381 (8) | |
C8 | 0.6353 (3) | 0.3882 (2) | 0.8843 (3) | 0.0381 (8) | |
C9 | 0.6796 (3) | 0.4123 (2) | 0.7986 (3) | 0.0416 (9) | |
H9 | 0.6369 | 0.4499 | 0.7477 | 0.050* | |
C10 | 0.7885 (3) | 0.3800 (2) | 0.7890 (3) | 0.0405 (8) | |
H10 | 0.8195 | 0.3975 | 0.7320 | 0.049* | |
C11 | 0.8520 (3) | 0.3221 (2) | 0.8632 (3) | 0.0371 (8) | |
C12 | 0.8054 (3) | 0.2985 (3) | 0.9479 (3) | 0.0456 (9) | |
H12 | 0.8471 | 0.2595 | 0.9980 | 0.055* | |
C13 | 0.6971 (3) | 0.3318 (3) | 0.9603 (3) | 0.0469 (9) | |
H13 | 0.6671 | 0.3163 | 1.0184 | 0.056* | |
C14 | 0.9689 (3) | 0.2868 (2) | 0.8542 (3) | 0.0406 (9) | |
C15 | 0.2607 (3) | 0.0891 (3) | 0.9274 (3) | 0.0595 (11) | |
H15 | 0.1821 | 0.0781 | 0.9252 | 0.071* | |
C16 | 0.3387 (3) | 0.0220 (3) | 0.9715 (3) | 0.0574 (11) | |
H16 | 0.3121 | −0.0328 | 0.9972 | 0.069* | |
C17 | 0.4563 (3) | 0.0358 (2) | 0.9778 (2) | 0.0366 (8) | |
C18 | 0.4870 (3) | 0.1191 (3) | 0.9397 (4) | 0.0705 (13) | |
H18 | 0.5652 | 0.1329 | 0.9436 | 0.085* | |
C19 | 0.4047 (3) | 0.1832 (3) | 0.8958 (4) | 0.0669 (13) | |
H19 | 0.4293 | 0.2390 | 0.8706 | 0.080* | |
C20 | 0.1584 (3) | 0.1482 (2) | 0.6235 (3) | 0.0406 (8) | |
H20 | 0.2228 | 0.1853 | 0.6208 | 0.049* | |
C21 | 0.1203 (3) | 0.0871 (2) | 0.5423 (2) | 0.0385 (8) | |
H21 | 0.1598 | 0.0829 | 0.4877 | 0.046* | |
C22 | 0.0233 (3) | 0.0324 (2) | 0.5434 (2) | 0.0314 (7) | |
C23 | −0.0299 (3) | 0.0406 (2) | 0.6283 (3) | 0.0442 (9) | |
H23 | −0.0954 | 0.0052 | 0.6325 | 0.053* | |
C24 | 0.0153 (3) | 0.1019 (2) | 0.7067 (3) | 0.0467 (9) | |
H24 | −0.0206 | 0.1054 | 0.7636 | 0.056* | |
O6 | 0.9603 (5) | 0.4138 (4) | 0.5754 (4) | 0.1208 (19) | 0.703 (5) |
H6B | 0.9770 | 0.3882 | 0.6345 | 0.181* | 0.703 (5) |
H6C | 0.9765 | 0.3761 | 0.5304 | 0.181* | 0.703 (5) |
O6B | 0.9064 (12) | 0.4388 (9) | 0.4695 (10) | 0.1208 (19) | 0.297 (5) |
H6D | 0.9428 | 0.4037 | 0.4223 | 0.181* | 0.297 (5) |
H6E | 0.9211 | 0.5044 | 0.4622 | 0.181* | 0.297 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0265 (2) | 0.0303 (2) | 0.0510 (3) | 0.00179 (19) | 0.00559 (17) | −0.00342 (19) |
O1 | 0.0376 (14) | 0.0380 (13) | 0.0618 (16) | −0.0068 (12) | 0.0191 (12) | −0.0064 (11) |
O2 | 0.118 (3) | 0.0579 (18) | 0.0629 (19) | −0.0229 (18) | 0.0322 (18) | −0.0125 (15) |
O3 | 0.0262 (13) | 0.0493 (14) | 0.0734 (17) | 0.0087 (12) | 0.0162 (12) | 0.0208 (13) |
O4 | 0.0310 (14) | 0.0374 (13) | 0.0730 (17) | 0.0042 (12) | 0.0153 (13) | 0.0008 (12) |
O5 | 0.0353 (14) | 0.0513 (15) | 0.0606 (16) | 0.0115 (13) | 0.0076 (12) | −0.0034 (12) |
N1 | 0.0316 (16) | 0.0347 (15) | 0.0502 (17) | 0.0009 (14) | 0.0072 (13) | 0.0031 (13) |
N2 | 0.0268 (15) | 0.0325 (15) | 0.0453 (16) | 0.0022 (13) | 0.0077 (13) | −0.0022 (12) |
C1 | 0.033 (2) | 0.0349 (19) | 0.052 (2) | 0.0017 (16) | 0.0061 (18) | 0.0000 (17) |
C2 | 0.0317 (19) | 0.0321 (18) | 0.050 (2) | 0.0047 (16) | 0.0156 (16) | 0.0053 (15) |
C3 | 0.036 (2) | 0.047 (2) | 0.075 (3) | 0.0111 (19) | 0.011 (2) | 0.014 (2) |
C4 | 0.058 (3) | 0.035 (2) | 0.100 (3) | 0.008 (2) | 0.027 (3) | 0.019 (2) |
C5 | 0.057 (3) | 0.033 (2) | 0.104 (3) | −0.012 (2) | 0.034 (3) | −0.005 (2) |
C6 | 0.036 (2) | 0.052 (2) | 0.073 (3) | −0.007 (2) | 0.0175 (19) | −0.001 (2) |
C7 | 0.030 (2) | 0.0299 (18) | 0.057 (2) | 0.0032 (16) | 0.0159 (17) | 0.0076 (16) |
C8 | 0.0212 (18) | 0.0358 (19) | 0.057 (2) | 0.0013 (15) | 0.0057 (16) | 0.0000 (16) |
C9 | 0.032 (2) | 0.0395 (19) | 0.053 (2) | 0.0026 (17) | 0.0068 (17) | 0.0071 (17) |
C10 | 0.034 (2) | 0.0352 (19) | 0.055 (2) | −0.0027 (17) | 0.0145 (17) | −0.0002 (16) |
C11 | 0.0235 (18) | 0.0328 (18) | 0.054 (2) | −0.0038 (15) | 0.0056 (16) | −0.0121 (16) |
C12 | 0.031 (2) | 0.050 (2) | 0.051 (2) | 0.0082 (18) | −0.0027 (17) | 0.0031 (17) |
C13 | 0.034 (2) | 0.055 (2) | 0.052 (2) | 0.0038 (19) | 0.0084 (17) | 0.0086 (18) |
C14 | 0.029 (2) | 0.0338 (18) | 0.056 (2) | −0.0012 (17) | 0.0000 (18) | −0.0129 (17) |
C15 | 0.026 (2) | 0.064 (3) | 0.088 (3) | 0.005 (2) | 0.011 (2) | 0.030 (2) |
C16 | 0.036 (2) | 0.049 (2) | 0.088 (3) | 0.0004 (19) | 0.013 (2) | 0.032 (2) |
C17 | 0.032 (2) | 0.0370 (19) | 0.0395 (19) | 0.0031 (16) | 0.0048 (15) | 0.0029 (14) |
C18 | 0.027 (2) | 0.060 (3) | 0.123 (4) | 0.004 (2) | 0.012 (2) | 0.034 (3) |
C19 | 0.028 (2) | 0.049 (2) | 0.123 (4) | −0.001 (2) | 0.013 (2) | 0.030 (2) |
C20 | 0.0291 (19) | 0.0398 (19) | 0.051 (2) | −0.0059 (16) | 0.0038 (17) | 0.0004 (16) |
C21 | 0.0325 (19) | 0.044 (2) | 0.0398 (19) | −0.0042 (17) | 0.0093 (15) | −0.0010 (16) |
C22 | 0.0296 (18) | 0.0255 (16) | 0.0378 (19) | 0.0064 (14) | 0.0034 (15) | 0.0051 (13) |
C23 | 0.041 (2) | 0.037 (2) | 0.057 (2) | −0.0132 (17) | 0.0156 (18) | −0.0093 (16) |
C24 | 0.050 (2) | 0.041 (2) | 0.054 (2) | −0.0069 (19) | 0.0228 (19) | −0.0104 (17) |
O6 | 0.141 (5) | 0.111 (4) | 0.116 (4) | 0.022 (4) | 0.040 (4) | 0.011 (3) |
O6B | 0.141 (5) | 0.111 (4) | 0.116 (4) | 0.022 (4) | 0.040 (4) | 0.011 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.964 (2) | C9—H9 | 0.9300 |
Cu1—O4i | 1.986 (2) | C10—C11 | 1.387 (4) |
Cu1—N1 | 2.004 (3) | C10—H10 | 0.9300 |
Cu1—N2 | 2.008 (3) | C11—C12 | 1.376 (5) |
Cu1—O2 | 2.661 (3) | C11—C14 | 1.487 (5) |
Cu1—O5i | 2.457 (3) | C12—C13 | 1.395 (5) |
O1—C1 | 1.275 (4) | C12—H12 | 0.9300 |
O2—C1 | 1.221 (4) | C13—H13 | 0.9300 |
O3—C8 | 1.386 (4) | C15—C16 | 1.375 (5) |
O3—C7 | 1.393 (4) | C15—H15 | 0.9300 |
O4—C14 | 1.275 (4) | C16—C17 | 1.381 (5) |
O4—Cu1ii | 1.986 (2) | C16—H16 | 0.9300 |
O5—C14 | 1.254 (4) | C17—C18 | 1.365 (5) |
N1—C15 | 1.329 (4) | C17—C17iii | 1.488 (6) |
N1—C19 | 1.330 (4) | C18—C19 | 1.377 (5) |
N2—C24 | 1.333 (4) | C18—H18 | 0.9300 |
N2—C20 | 1.335 (4) | C19—H19 | 0.9300 |
C1—C2 | 1.500 (4) | C20—C21 | 1.390 (4) |
C2—C7 | 1.391 (5) | C20—H20 | 0.9300 |
C2—C3 | 1.396 (4) | C21—C22 | 1.382 (4) |
C3—C4 | 1.390 (5) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C22—C23 | 1.388 (5) |
C4—C5 | 1.374 (5) | C22—C22iv | 1.494 (6) |
C4—H4 | 0.9300 | C23—C24 | 1.383 (4) |
C5—C6 | 1.377 (5) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C6—C7 | 1.379 (5) | O6—H6B | 0.8503 |
C6—H6A | 0.9300 | O6—H6C | 0.8498 |
C8—C9 | 1.375 (5) | O6B—H6D | 0.9600 |
C8—C13 | 1.381 (4) | O6B—H6E | 0.9600 |
C9—C10 | 1.387 (5) | | |
| | | |
O1—Cu1—O4i | 91.80 (10) | C8—C9—H9 | 120.4 |
O1—Cu1—N1 | 94.69 (11) | C10—C9—H9 | 120.4 |
O4i—Cu1—N1 | 156.51 (11) | C9—C10—C11 | 121.0 (3) |
O1—Cu1—N2 | 151.80 (11) | C9—C10—H10 | 119.5 |
O4i—Cu1—N2 | 91.30 (10) | C11—C10—H10 | 119.5 |
N1—Cu1—N2 | 93.52 (11) | C12—C11—C10 | 118.6 (3) |
O2—Cu1—N1 | 96.94 (10) | C12—C11—C14 | 119.7 (3) |
O2—Cu1—N2 | 98.10 (10) | C10—C11—C14 | 121.7 (3) |
O2—Cu1—O1 | 54.13 (10) | C11—C12—C13 | 121.5 (3) |
O2—Cu1—O4i | 105.11 (10) | C11—C12—H12 | 119.3 |
O2—Cu1—O5i | 159.93 (9) | C13—C12—H12 | 119.3 |
O1—Cu1—O5i | 111.56 (9) | C8—C13—C12 | 118.5 (3) |
N1—Cu1—O5i | 98.41 (9) | C8—C13—H13 | 120.7 |
N2—Cu1—O5i | 93.80 (9) | C12—C13—H13 | 120.7 |
O4i—Cu1—O5i | 58.31 (9) | O5—C14—O4 | 121.2 (3) |
C1—O1—Cu1 | 107.0 (2) | O5—C14—C11 | 120.5 (4) |
C8—O3—C7 | 118.9 (3) | O4—C14—C11 | 118.3 (3) |
C14—O4—Cu1ii | 100.7 (2) | N1—C15—C16 | 123.7 (3) |
C15—N1—C19 | 116.3 (3) | N1—C15—H15 | 118.2 |
C15—N1—Cu1 | 119.5 (2) | C16—C15—H15 | 118.2 |
C19—N1—Cu1 | 124.1 (2) | C15—C16—C17 | 120.2 (3) |
C24—N2—C20 | 116.6 (3) | C15—C16—H16 | 119.9 |
C24—N2—Cu1 | 125.2 (2) | C17—C16—H16 | 119.9 |
C20—N2—Cu1 | 118.1 (2) | C18—C17—C16 | 115.6 (3) |
O2—C1—O1 | 123.1 (3) | C18—C17—C17iii | 122.3 (4) |
O2—C1—C2 | 121.5 (3) | C16—C17—C17iii | 122.1 (4) |
O1—C1—C2 | 115.4 (3) | C17—C18—C19 | 121.4 (4) |
C7—C2—C3 | 117.4 (3) | C17—C18—H18 | 119.3 |
C7—C2—C1 | 120.9 (3) | C19—C18—H18 | 119.3 |
C3—C2—C1 | 121.7 (3) | N1—C19—C18 | 122.8 (4) |
C4—C3—C2 | 120.4 (4) | N1—C19—H19 | 118.6 |
C4—C3—H3 | 119.8 | C18—C19—H19 | 118.6 |
C2—C3—H3 | 119.8 | N2—C20—C21 | 123.5 (3) |
C5—C4—C3 | 120.4 (4) | N2—C20—H20 | 118.3 |
C5—C4—H4 | 119.8 | C21—C20—H20 | 118.3 |
C3—C4—H4 | 119.8 | C22—C21—C20 | 119.5 (3) |
C4—C5—C6 | 120.4 (4) | C22—C21—H21 | 120.3 |
C4—C5—H5 | 119.8 | C20—C21—H21 | 120.3 |
C6—C5—H5 | 119.8 | C21—C22—C23 | 117.2 (3) |
C5—C6—C7 | 118.9 (4) | C21—C22—C22iv | 121.6 (4) |
C5—C6—H6A | 120.5 | C23—C22—C22iv | 121.2 (4) |
C7—C6—H6A | 120.5 | C24—C23—C22 | 119.4 (3) |
C6—C7—C2 | 122.4 (3) | C24—C23—H23 | 120.3 |
C6—C7—O3 | 121.0 (3) | C22—C23—H23 | 120.3 |
C2—C7—O3 | 116.5 (3) | N2—C24—C23 | 123.8 (3) |
C9—C8—C13 | 121.1 (3) | N2—C24—H24 | 118.1 |
C9—C8—O3 | 123.5 (3) | C23—C24—H24 | 118.1 |
C13—C8—O3 | 115.2 (3) | H6B—O6—H6C | 109.1 |
C8—C9—C10 | 119.3 (3) | H6D—O6B—H6E | 109.5 |
| | | |
Cu1—O1—C1—O2 | −7.2 (4) | O3—C8—C13—C12 | 175.8 (3) |
Cu1—O1—C1—C2 | 174.1 (2) | C11—C12—C13—C8 | 1.2 (5) |
O2—C1—C2—C7 | −96.8 (4) | Cu1ii—O4—C14—O5 | −2.4 (4) |
O1—C1—C2—C7 | 81.9 (4) | Cu1ii—O4—C14—C11 | 178.0 (2) |
O2—C1—C2—C3 | 84.4 (5) | C12—C11—C14—O5 | 11.5 (5) |
O1—C1—C2—C3 | −96.9 (4) | C10—C11—C14—O5 | −169.5 (3) |
C7—C2—C3—C4 | −1.1 (5) | C12—C11—C14—O4 | −168.8 (3) |
C1—C2—C3—C4 | 177.8 (4) | C10—C11—C14—O4 | 10.1 (5) |
C2—C3—C4—C5 | 0.1 (6) | C19—N1—C15—C16 | −2.3 (6) |
C3—C4—C5—C6 | 0.1 (7) | Cu1—N1—C15—C16 | 173.1 (3) |
C4—C5—C6—C7 | 0.7 (6) | N1—C15—C16—C17 | 0.8 (7) |
C5—C6—C7—C2 | −1.8 (6) | C15—C16—C17—C18 | 1.2 (6) |
C5—C6—C7—O3 | −177.5 (3) | C15—C16—C17—C17iii | −178.3 (4) |
C3—C2—C7—C6 | 1.9 (5) | C16—C17—C18—C19 | −1.7 (6) |
C1—C2—C7—C6 | −176.9 (3) | C17iii—C17—C18—C19 | 177.8 (4) |
C3—C2—C7—O3 | 177.9 (3) | C15—N1—C19—C18 | 1.7 (6) |
C1—C2—C7—O3 | −1.0 (5) | Cu1—N1—C19—C18 | −173.4 (4) |
C8—O3—C7—C6 | −55.3 (5) | C17—C18—C19—N1 | 0.2 (8) |
C8—O3—C7—C2 | 128.7 (3) | C24—N2—C20—C21 | 0.1 (5) |
C7—O3—C8—C9 | −28.5 (5) | Cu1—N2—C20—C21 | −176.5 (2) |
C7—O3—C8—C13 | 155.1 (3) | N2—C20—C21—C22 | 1.3 (5) |
C13—C8—C9—C10 | −0.6 (5) | C20—C21—C22—C23 | −1.3 (5) |
O3—C8—C9—C10 | −176.8 (3) | C20—C21—C22—C22iv | 178.2 (3) |
C8—C9—C10—C11 | 1.5 (5) | C21—C22—C23—C24 | 0.1 (5) |
C9—C10—C11—C12 | −1.1 (5) | C22iv—C22—C23—C24 | −179.5 (3) |
C9—C10—C11—C14 | 179.9 (3) | C20—N2—C24—C23 | −1.5 (5) |
C10—C11—C12—C13 | −0.2 (5) | Cu1—N2—C24—C23 | 174.9 (3) |
C14—C11—C12—C13 | 178.7 (3) | C22—C23—C24—N2 | 1.4 (6) |
C9—C8—C13—C12 | −0.7 (5) | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+2; (iv) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
C20—H20···O2 | 0.93 | 2.64 | 3.365 (4) | 135 |
C21—H21···O1vi | 0.93 | 2.34 | 3.232 (4) | 160 |
C24—H24···O5i | 0.93 | 2.58 | 3.239 (4) | 128 |
O6—H6B···O4 | 0.85 | 2.17 | 3.019 (6) | 179 |
O6—H6C···O5vi | 0.85 | 2.22 | 3.070 (6) | 179 |
O6B—H6D···O5vi | 0.96 | 2.04 | 2.829 (13) | 139 |
O6B—H6E···O6Bv | 0.96 | 2.21 | 2.80 (3) | 119 |
Symmetry codes: (i) x−1, y, z; (v) −x+2, −y+1, −z+1; (vi) x, −y+1/2, z−1/2. |
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