metal-organic compounds
The coordination environment of copper(II) in the title compound, [Cu(C6H4NO3)(NO3)(C12H8N2)], is square pyramidal; the basal plane comprises the two N atoms of 1,10-phenanthroline and the two O atoms of picolinate N-oxide, with the apical position occupied by a nitrate O atom.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002515/ng6094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002515/ng6094Isup2.hkl |
CCDC reference: 269825
Computing details top
Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXTL (Siemens, 1995).
Crystal data top
[Cu(C6H4NO3)(NO3)(C12H8N2)] | F(000) = 900 |
Mr = 443.86 | Dx = 1.797 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2861 (11) Å | Cell parameters from 6799 reflections |
b = 9.5829 (12) Å | θ = 3.1–27.4° |
c = 18.438 (3) Å | µ = 1.38 mm−1 |
β = 90.750 (4)° | T = 298 K |
V = 1640.7 (4) Å3 | Block, blue |
Z = 4 | 0.38 × 0.24 × 0.16 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 3713 independent reflections |
Radiation source: rotating anode | 2699 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
oscillation scans | θmax = 27.4°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→12 |
Tmin = 0.678, Tmax = 0.802 | k = −12→12 |
6799 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0434P)2] where P = (Fo2 + 2Fc2)/3 |
3713 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.66658 (3) | 0.59025 (3) | 0.453019 (14) | 0.02234 (9) | |
N1 | 0.8553 (2) | 0.3662 (2) | 0.41059 (10) | 0.0238 (4) | |
N2 | 0.50419 (19) | 0.7284 (2) | 0.45946 (10) | 0.0230 (4) | |
N3 | 0.66362 (19) | 0.60701 (19) | 0.56160 (10) | 0.0222 (4) | |
N4 | 0.9079 (2) | 0.7727 (2) | 0.38519 (11) | 0.0288 (5) | |
O1 | 0.79083 (18) | 0.43446 (17) | 0.46404 (8) | 0.0300 (4) | |
O2 | 0.63850 (17) | 0.56135 (17) | 0.35177 (8) | 0.0276 (4) | |
O3 | 0.7050 (2) | 0.4924 (2) | 0.24319 (9) | 0.0485 (6) | |
O4 | 0.81773 (17) | 0.77543 (17) | 0.43708 (9) | 0.0298 (4) | |
O5 | 0.9285 (3) | 0.8807 (2) | 0.35122 (14) | 0.0711 (8) | |
O6 | 0.9709 (2) | 0.66392 (19) | 0.36937 (10) | 0.0388 (5) | |
C1 | 0.7146 (3) | 0.4877 (3) | 0.30903 (13) | 0.0267 (5) | |
C2 | 0.8245 (2) | 0.3827 (2) | 0.33891 (12) | 0.0232 (5) | |
C3 | 0.8962 (3) | 0.2983 (2) | 0.28963 (13) | 0.0264 (5) | |
H3A | 0.8771 | 0.3087 | 0.2403 | 0.032* | |
C4 | 0.9949 (3) | 0.1998 (3) | 0.31236 (13) | 0.0305 (6) | |
H4A | 1.0406 | 0.1424 | 0.2791 | 0.037* | |
C5 | 1.0241 (3) | 0.1882 (3) | 0.38572 (14) | 0.0329 (6) | |
H5A | 1.0909 | 0.1229 | 0.4023 | 0.039* | |
C6 | 0.9555 (3) | 0.2724 (3) | 0.43404 (13) | 0.0292 (6) | |
H6A | 0.9775 | 0.2655 | 0.4833 | 0.035* | |
C7 | 0.4230 (3) | 0.7838 (3) | 0.40753 (13) | 0.0267 (5) | |
H7A | 0.4359 | 0.7541 | 0.3601 | 0.032* | |
C8 | 0.3186 (3) | 0.8854 (2) | 0.42103 (13) | 0.0286 (6) | |
H8A | 0.2630 | 0.9217 | 0.3832 | 0.034* | |
C9 | 0.2990 (3) | 0.9309 (2) | 0.49068 (13) | 0.0271 (5) | |
H9A | 0.2301 | 0.9986 | 0.5003 | 0.032* | |
C10 | 0.3836 (2) | 0.8749 (2) | 0.54779 (12) | 0.0240 (5) | |
C11 | 0.3709 (2) | 0.9136 (3) | 0.62238 (12) | 0.0262 (5) | |
H11A | 0.3042 | 0.9812 | 0.6354 | 0.031* | |
C12 | 0.4545 (2) | 0.8531 (2) | 0.67456 (12) | 0.0249 (5) | |
H12A | 0.4453 | 0.8814 | 0.7225 | 0.030* | |
C13 | 0.5565 (2) | 0.7466 (2) | 0.65719 (12) | 0.0243 (5) | |
C14 | 0.6439 (2) | 0.6758 (2) | 0.70823 (13) | 0.0265 (5) | |
H14A | 0.6399 | 0.6990 | 0.7571 | 0.032* | |
C15 | 0.7347 (3) | 0.5727 (2) | 0.68552 (13) | 0.0287 (6) | |
H15A | 0.7905 | 0.5236 | 0.7191 | 0.034* | |
C16 | 0.7434 (3) | 0.5412 (3) | 0.61153 (13) | 0.0255 (5) | |
H16A | 0.8069 | 0.4721 | 0.5968 | 0.031* | |
C17 | 0.5708 (2) | 0.7077 (2) | 0.58373 (12) | 0.0215 (5) | |
C18 | 0.4837 (2) | 0.7724 (2) | 0.52883 (12) | 0.0232 (5) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.02700 (16) | 0.02164 (15) | 0.01845 (15) | 0.00103 (13) | 0.00293 (10) | −0.00067 (13) |
N1 | 0.0280 (11) | 0.0219 (10) | 0.0216 (10) | 0.0013 (8) | 0.0032 (8) | 0.0002 (8) |
N2 | 0.0256 (10) | 0.0241 (11) | 0.0193 (10) | −0.0025 (8) | 0.0028 (8) | −0.0004 (8) |
N3 | 0.0254 (10) | 0.0202 (10) | 0.0210 (9) | −0.0024 (8) | 0.0034 (8) | 0.0000 (8) |
N4 | 0.0317 (12) | 0.0278 (12) | 0.0271 (11) | −0.0014 (9) | 0.0026 (9) | 0.0002 (9) |
O1 | 0.0418 (10) | 0.0296 (10) | 0.0188 (8) | 0.0113 (8) | 0.0060 (7) | −0.0008 (7) |
O2 | 0.0302 (9) | 0.0320 (10) | 0.0207 (8) | 0.0092 (7) | 0.0005 (7) | −0.0024 (7) |
O3 | 0.0623 (13) | 0.0648 (14) | 0.0184 (9) | 0.0332 (11) | −0.0001 (9) | −0.0028 (9) |
O4 | 0.0353 (10) | 0.0279 (9) | 0.0266 (9) | −0.0046 (8) | 0.0097 (7) | −0.0022 (8) |
O5 | 0.1004 (19) | 0.0323 (12) | 0.0823 (18) | 0.0106 (12) | 0.0601 (15) | 0.0173 (12) |
O6 | 0.0436 (11) | 0.0305 (10) | 0.0424 (11) | 0.0127 (9) | 0.0116 (9) | 0.0024 (9) |
C1 | 0.0298 (13) | 0.0271 (13) | 0.0232 (12) | 0.0023 (11) | 0.0002 (10) | 0.0002 (11) |
C2 | 0.0253 (12) | 0.0216 (13) | 0.0227 (12) | −0.0019 (10) | 0.0034 (9) | 0.0007 (10) |
C3 | 0.0287 (13) | 0.0266 (13) | 0.0239 (12) | −0.0019 (10) | 0.0025 (10) | −0.0004 (10) |
C4 | 0.0293 (13) | 0.0289 (14) | 0.0334 (14) | 0.0037 (11) | 0.0083 (11) | −0.0038 (12) |
C5 | 0.0314 (14) | 0.0278 (13) | 0.0394 (15) | 0.0063 (11) | 0.0028 (11) | 0.0042 (12) |
C6 | 0.0312 (13) | 0.0296 (13) | 0.0267 (13) | 0.0038 (11) | −0.0006 (10) | 0.0061 (11) |
C7 | 0.0301 (13) | 0.0303 (14) | 0.0197 (12) | −0.0001 (11) | 0.0026 (10) | −0.0006 (10) |
C8 | 0.0326 (13) | 0.0271 (14) | 0.0262 (13) | 0.0007 (11) | 0.0021 (10) | 0.0031 (11) |
C9 | 0.0280 (13) | 0.0254 (13) | 0.0278 (12) | 0.0018 (10) | 0.0041 (10) | 0.0004 (11) |
C10 | 0.0264 (12) | 0.0208 (12) | 0.0248 (12) | −0.0034 (9) | 0.0056 (10) | 0.0016 (10) |
C11 | 0.0290 (12) | 0.0247 (12) | 0.0251 (12) | −0.0016 (11) | 0.0077 (9) | −0.0048 (11) |
C12 | 0.0292 (13) | 0.0269 (12) | 0.0186 (12) | −0.0055 (10) | 0.0056 (10) | −0.0032 (10) |
C13 | 0.0263 (12) | 0.0240 (12) | 0.0227 (12) | −0.0069 (10) | 0.0052 (9) | −0.0009 (10) |
C14 | 0.0306 (13) | 0.0301 (13) | 0.0187 (11) | −0.0056 (11) | 0.0013 (10) | −0.0017 (10) |
C15 | 0.0327 (13) | 0.0280 (14) | 0.0253 (12) | −0.0038 (11) | −0.0015 (10) | 0.0060 (11) |
C16 | 0.0288 (12) | 0.0233 (12) | 0.0243 (12) | −0.0001 (10) | 0.0018 (10) | 0.0017 (10) |
C17 | 0.0236 (12) | 0.0198 (12) | 0.0212 (11) | −0.0042 (9) | 0.0027 (9) | 0.0000 (10) |
C18 | 0.0278 (12) | 0.0208 (12) | 0.0210 (12) | −0.0054 (10) | 0.0060 (9) | 0.0002 (10) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.8962 (16) | C5—C6 | 1.365 (3) |
Cu1—O2 | 1.9018 (16) | C5—H5A | 0.9300 |
Cu1—O4 | 2.2839 (16) | C6—H6A | 0.9300 |
Cu1—N2 | 2.0113 (19) | C7—C8 | 1.398 (3) |
Cu1—N3 | 2.0090 (19) | C7—H7A | 0.9300 |
N1—O1 | 1.332 (2) | C8—C9 | 1.371 (3) |
N1—C2 | 1.358 (3) | C8—H8A | 0.9300 |
N1—C6 | 1.361 (3) | C9—C10 | 1.411 (3) |
N2—C7 | 1.322 (3) | C9—H9A | 0.9300 |
N2—C18 | 1.363 (3) | C10—C18 | 1.400 (3) |
N3—C16 | 1.333 (3) | C10—C11 | 1.431 (3) |
N3—C17 | 1.360 (3) | C11—C12 | 1.358 (3) |
N4—O5 | 1.226 (3) | C11—H11A | 0.9300 |
N4—O6 | 1.232 (2) | C12—C13 | 1.432 (3) |
N4—O4 | 1.280 (2) | C12—H12A | 0.9300 |
O2—C1 | 1.278 (3) | C13—C14 | 1.409 (3) |
O3—C1 | 1.217 (3) | C13—C17 | 1.413 (3) |
C1—C2 | 1.531 (3) | C14—C15 | 1.368 (3) |
C2—C3 | 1.393 (3) | C14—H14A | 0.9300 |
C3—C4 | 1.377 (3) | C15—C16 | 1.401 (3) |
C3—H3A | 0.9300 | C15—H15A | 0.9300 |
C4—C5 | 1.381 (3) | C16—H16A | 0.9300 |
C4—H4A | 0.9300 | C17—C18 | 1.429 (3) |
O1—Cu1—O2 | 93.78 (7) | N1—C6—C5 | 120.4 (2) |
O1—Cu1—O4 | 104.56 (7) | N1—C6—H6A | 119.8 |
O1—Cu1—N2 | 165.37 (7) | C5—C6—H6A | 119.8 |
O1—Cu1—N3 | 88.42 (7) | N2—C7—C8 | 122.7 (2) |
O2—Cu1—O4 | 93.64 (7) | N2—C7—H7A | 118.6 |
O2—Cu1—N2 | 93.47 (7) | C8—C7—H7A | 118.6 |
O2—Cu1—N3 | 170.52 (7) | C9—C8—C7 | 119.3 (2) |
O4—Cu1—N2 | 87.63 (7) | C9—C8—H8A | 120.4 |
O4—Cu1—N3 | 94.73 (7) | C7—C8—H8A | 120.4 |
N2—Cu1—N3 | 82.45 (7) | C8—C9—C10 | 119.9 (2) |
O1—N1—C2 | 124.92 (19) | C8—C9—H9A | 120.0 |
O1—N1—C6 | 113.68 (18) | C10—C9—H9A | 120.0 |
C2—N1—C6 | 121.4 (2) | C18—C10—C9 | 116.4 (2) |
C7—N2—C18 | 118.0 (2) | C18—C10—C11 | 119.0 (2) |
C7—N2—Cu1 | 129.98 (16) | C9—C10—C11 | 124.5 (2) |
C18—N2—Cu1 | 111.91 (15) | C12—C11—C10 | 121.1 (2) |
C16—N3—C17 | 118.50 (19) | C12—C11—H11A | 119.4 |
C16—N3—Cu1 | 129.48 (16) | C10—C11—H11A | 119.4 |
C17—N3—Cu1 | 111.89 (15) | C11—C12—C13 | 121.3 (2) |
O5—N4—O6 | 121.0 (2) | C11—C12—H12A | 119.4 |
O5—N4—O4 | 118.2 (2) | C13—C12—H12A | 119.4 |
O6—N4—O4 | 120.8 (2) | C14—C13—C17 | 116.9 (2) |
N1—O1—Cu1 | 125.90 (13) | C14—C13—C12 | 124.8 (2) |
C1—O2—Cu1 | 128.02 (16) | C17—C13—C12 | 118.3 (2) |
N4—O4—Cu1 | 119.29 (14) | C15—C14—C13 | 119.7 (2) |
O3—C1—O2 | 124.2 (2) | C15—C14—H14A | 120.2 |
O3—C1—C2 | 115.0 (2) | C13—C14—H14A | 120.2 |
O2—C1—C2 | 120.8 (2) | C14—C15—C16 | 119.8 (2) |
N1—C2—C3 | 118.1 (2) | C14—C15—H15A | 120.1 |
N1—C2—C1 | 123.9 (2) | C16—C15—H15A | 120.1 |
C3—C2—C1 | 118.0 (2) | N3—C16—C15 | 122.1 (2) |
C4—C3—C2 | 121.4 (2) | N3—C16—H16A | 118.9 |
C4—C3—H3A | 119.3 | C15—C16—H16A | 118.9 |
C2—C3—H3A | 119.3 | N3—C17—C13 | 122.9 (2) |
C3—C4—C5 | 118.3 (2) | N3—C17—C18 | 116.8 (2) |
C3—C4—H4A | 120.8 | C13—C17—C18 | 120.3 (2) |
C5—C4—H4A | 120.8 | N2—C18—C10 | 123.6 (2) |
C6—C5—C4 | 120.3 (2) | N2—C18—C17 | 116.5 (2) |
C6—C5—H5A | 119.8 | C10—C18—C17 | 120.0 (2) |
C4—C5—H5A | 119.8 |