Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005680/qa0277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005680/qa0277Isup2.hkl |
CCDC reference: 145645
In the present study, single crystals of (I) were grown from an acetonitrile solution as needles elongated along a.
Positional parameters of all the H atoms were calculated geometrically and fixed with U(H) = 1.2Ueq(parent atom).
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
[Cu2(C19H18N3O)2](ClO4)2 | Dx = 1.642 Mg m−3 |
Mr = 934.74 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/n | Cell parameters from 25 reflections |
a = 11.380 (1) Å | θ = 10–15° |
b = 9.877 (2) Å | µ = 1.33 mm−1 |
c = 17.400 (2) Å | T = 298 K |
β = 104.79 (1)° | Needle, green |
V = 1891.0 (5) Å3 | 0.7 × 0.15 × 0.1 mm |
Z = 2 |
Rigaku AFC-5S diffractometer | Rint = 0.059 |
θ–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→15 |
Tmin = 0.662, Tmax = 0.897 | k = 0→13 |
4819 measured reflections | l = −23→23 |
4338 independent reflections | 3 standard reflections every 100 reflections |
2393 reflections with I > 2σ(I) | intensity decay: 5.5% |
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.185 | (Δ/σ)max = 0.009 |
S = 0.98 | Δρmax = 0.59 e Å−3 |
4338 reflections | Δρmin = −0.63 e Å−3 |
262 parameters |
[Cu2(C19H18N3O)2](ClO4)2 | V = 1891.0 (5) Å3 |
Mr = 934.74 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.380 (1) Å | µ = 1.33 mm−1 |
b = 9.877 (2) Å | T = 298 K |
c = 17.400 (2) Å | 0.7 × 0.15 × 0.1 mm |
β = 104.79 (1)° |
Rigaku AFC-5S diffractometer | 2393 reflections with I > 2σ(I) |
Absorption correction: integration (Coppens et al., 1965) | Rint = 0.059 |
Tmin = 0.662, Tmax = 0.897 | 3 standard reflections every 100 reflections |
4819 measured reflections | intensity decay: 5.5% |
4338 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 262 parameters |
wR(F2) = 0.185 | H-atom parameters not refined |
S = 0.98 | Δρmax = 0.59 e Å−3 |
4338 reflections | Δρmin = −0.63 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.54358 (6) | 0.02660 (8) | 0.42187 (4) | 0.0373 (2) | |
Cl1 | 0.4955 (1) | 0.2387 (2) | 0.1692 (1) | 0.0603 (5) | |
O1 | 0.6029 (3) | −0.0563 (4) | 0.5432 (2) | 0.043 (1) | |
O2 | 0.5814 (5) | 0.1502 (6) | 0.1495 (4) | 0.085 (2) | |
O3 | 0.4568 (5) | 0.179 (1) | 0.2322 (4) | 0.142 (3) | |
O4 | 0.3945 (6) | 0.2534 (9) | 0.1043 (4) | 0.126 (3) | |
O5 | 0.5546 (7) | 0.3610 (9) | 0.1932 (7) | 0.160 (4) | |
N1 | 0.6163 (4) | 0.2133 (6) | 0.4286 (3) | 0.045 (1) | |
N2 | 0.7031 (4) | −0.0249 (6) | 0.3969 (3) | 0.043 (1) | |
N3 | 0.4837 (4) | −0.1444 (5) | 0.3634 (3) | 0.038 (1) | |
C1 | 0.5920 (5) | 0.3222 (6) | 0.4677 (4) | 0.045 (2) | |
C2 | 0.6567 (7) | 0.4417 (7) | 0.4739 (4) | 0.059 (2) | |
C3 | 0.7500 (7) | 0.4480 (9) | 0.4364 (5) | 0.071 (3) | |
C4 | 0.7756 (6) | 0.3392 (9) | 0.3949 (4) | 0.064 (2) | |
C5 | 0.7093 (5) | 0.2212 (7) | 0.3932 (4) | 0.050 (2) | |
C6 | 0.7315 (5) | 0.0962 (8) | 0.3523 (4) | 0.057 (2) | |
C7 | 0.6918 (6) | −0.1505 (8) | 0.3492 (4) | 0.062 (2) | |
C8 | 0.5683 (5) | −0.2142 (7) | 0.3366 (3) | 0.044 (2) | |
C9 | 0.5431 (6) | −0.3391 (7) | 0.3010 (4) | 0.053 (2) | |
C10 | 0.4301 (7) | −0.3950 (7) | 0.2919 (4) | 0.060 (2) | |
C11 | 0.3438 (6) | −0.3230 (7) | 0.3184 (4) | 0.054 (2) | |
C12 | 0.3731 (5) | −0.1988 (7) | 0.3528 (3) | 0.044 (2) | |
C13 | 0.8019 (4) | −0.0359 (7) | 0.4726 (3) | 0.043 (2) | |
C14 | 0.7886 (5) | −0.1479 (6) | 0.5270 (4) | 0.043 (2) | |
C15 | 0.8802 (5) | −0.2459 (7) | 0.5490 (4) | 0.049 (2) | |
C16 | 0.8783 (6) | −0.3425 (7) | 0.6050 (5) | 0.058 (2) | |
C17 | 0.7859 (5) | −0.3416 (7) | 0.6435 (4) | 0.051 (2) | |
C18 | 0.6940 (5) | −0.2455 (6) | 0.6239 (3) | 0.043 (2) | |
C19 | 0.6923 (4) | −0.1495 (6) | 0.5647 (3) | 0.036 (1) | |
H1 | 0.5260 | 0.3169 | 0.4927 | 0.0543* | |
H2 | 0.6377 | 0.5175 | 0.5031 | 0.0707* | |
H3 | 0.7970 | 0.5294 | 0.4395 | 0.0847* | |
H4 | 0.8388 | 0.3444 | 0.3675 | 0.0764* | |
H5 | 0.8152 | 0.0931 | 0.3507 | 0.0682* | |
H6 | 0.6803 | 0.0956 | 0.2991 | 0.0682* | |
H7 | 0.7055 | −0.1293 | 0.2984 | 0.0744* | |
H8 | 0.7520 | −0.2140 | 0.3764 | 0.0744* | |
H9 | 0.6043 | −0.3867 | 0.2827 | 0.0633* | |
H10 | 0.4112 | −0.4824 | 0.2676 | 0.0720* | |
H11 | 0.2639 | −0.3598 | 0.3125 | 0.0646* | |
H12 | 0.3120 | −0.1490 | 0.3700 | 0.0533* | |
H13 | 0.8776 | −0.0486 | 0.4587 | 0.0515* | |
H14 | 0.8043 | 0.0478 | 0.5011 | 0.0515* | |
H15 | 0.9463 | −0.2452 | 0.5239 | 0.0588* | |
H16 | 0.9407 | −0.4104 | 0.6175 | 0.0699* | |
H17 | 0.7853 | −0.4077 | 0.6839 | 0.0617* | |
H18 | 0.6308 | −0.2451 | 0.6514 | 0.0520* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0240 (3) | 0.0473 (4) | 0.0441 (4) | 0.0030 (3) | 0.0155 (2) | −0.0071 (4) |
Cl1 | 0.0362 (8) | 0.084 (1) | 0.066 (1) | −0.0073 (8) | 0.0239 (7) | −0.0120 (9) |
O1 | 0.031 (2) | 0.055 (3) | 0.046 (2) | 0.011 (2) | 0.018 (2) | −0.006 (2) |
O2 | 0.074 (3) | 0.068 (4) | 0.132 (5) | −0.007 (3) | 0.063 (3) | −0.011 (3) |
O3 | 0.054 (3) | 0.30 (1) | 0.078 (4) | −0.010 (5) | 0.031 (3) | 0.034 (6) |
O4 | 0.071 (4) | 0.187 (9) | 0.104 (5) | 0.017 (5) | −0.004 (4) | 0.041 (5) |
O5 | 0.106 (5) | 0.122 (7) | 0.28 (1) | −0.033 (5) | 0.098 (7) | −0.113 (7) |
N1 | 0.030 (2) | 0.054 (3) | 0.049 (3) | 0.003 (2) | 0.012 (2) | 0.003 (2) |
N2 | 0.029 (2) | 0.059 (3) | 0.045 (3) | 0.001 (2) | 0.015 (2) | −0.009 (3) |
N3 | 0.034 (2) | 0.050 (3) | 0.034 (2) | 0.006 (2) | 0.015 (2) | −0.005 (2) |
C1 | 0.044 (3) | 0.041 (4) | 0.050 (3) | 0.003 (3) | 0.010 (3) | 0.004 (3) |
C2 | 0.062 (4) | 0.040 (4) | 0.069 (4) | 0.005 (3) | 0.006 (3) | −0.004 (3) |
C3 | 0.060 (4) | 0.063 (6) | 0.087 (5) | −0.012 (4) | 0.015 (4) | 0.017 (4) |
C4 | 0.045 (4) | 0.083 (6) | 0.063 (4) | −0.008 (4) | 0.015 (3) | 0.024 (4) |
C5 | 0.033 (3) | 0.069 (5) | 0.047 (4) | 0.004 (3) | 0.011 (3) | 0.016 (3) |
C6 | 0.036 (3) | 0.093 (6) | 0.047 (4) | 0.005 (3) | 0.020 (3) | 0.009 (4) |
C7 | 0.038 (3) | 0.077 (5) | 0.076 (5) | 0.002 (3) | 0.024 (3) | −0.031 (4) |
C8 | 0.039 (3) | 0.056 (4) | 0.041 (3) | 0.010 (3) | 0.016 (2) | −0.002 (3) |
C9 | 0.056 (4) | 0.056 (4) | 0.051 (4) | 0.012 (3) | 0.022 (3) | −0.007 (3) |
C10 | 0.064 (4) | 0.050 (4) | 0.066 (4) | 0.005 (3) | 0.017 (4) | −0.011 (3) |
C11 | 0.044 (3) | 0.054 (4) | 0.064 (4) | −0.003 (3) | 0.013 (3) | −0.001 (3) |
C12 | 0.036 (3) | 0.055 (4) | 0.044 (3) | 0.006 (3) | 0.013 (2) | −0.001 (3) |
C13 | 0.021 (2) | 0.061 (4) | 0.050 (3) | 0.005 (3) | 0.015 (2) | 0.002 (3) |
C14 | 0.031 (3) | 0.042 (3) | 0.059 (4) | 0.006 (3) | 0.017 (3) | 0.001 (3) |
C15 | 0.032 (3) | 0.049 (4) | 0.070 (4) | 0.010 (3) | 0.022 (3) | −0.002 (3) |
C16 | 0.042 (3) | 0.050 (4) | 0.085 (5) | 0.011 (3) | 0.022 (3) | 0.003 (4) |
C17 | 0.042 (3) | 0.050 (4) | 0.061 (4) | 0.002 (3) | 0.010 (3) | 0.001 (3) |
C18 | 0.033 (3) | 0.051 (4) | 0.046 (3) | −0.004 (3) | 0.009 (2) | −0.004 (3) |
C19 | 0.026 (2) | 0.043 (3) | 0.041 (3) | 0.007 (2) | 0.011 (2) | −0.005 (3) |
Cu1—O1 | 2.203 (4) | C6—H5 | 0.960 |
Cu1—O1i | 1.938 (3) | C6—H6 | 0.960 |
Cu1—N1 | 2.013 (5) | C7—C8 | 1.503 (9) |
Cu1—N2 | 2.037 (4) | C7—H7 | 0.959 |
Cu1—N3 | 2.000 (5) | C7—H8 | 0.960 |
Cl1—O2 | 1.416 (6) | C8—C9 | 1.377 (9) |
Cl1—O3 | 1.411 (7) | C9—C10 | 1.371 (10) |
Cl1—O4 | 1.398 (6) | C9—H9 | 0.960 |
Cl1—O5 | 1.393 (7) | C10—C11 | 1.383 (9) |
O1—C19 | 1.352 (6) | C10—H10 | 0.961 |
N1—C1 | 1.338 (8) | C11—C12 | 1.368 (9) |
N1—C5 | 1.357 (7) | C11—H11 | 0.960 |
N2—C6 | 1.505 (9) | C12—H12 | 0.960 |
N2—C7 | 1.479 (8) | C13—C14 | 1.488 (8) |
N2—C13 | 1.502 (7) | C13—H13 | 0.960 |
N3—C8 | 1.359 (7) | C13—H14 | 0.960 |
N3—C12 | 1.338 (7) | C14—C15 | 1.402 (8) |
C1—C2 | 1.381 (9) | C14—C19 | 1.414 (7) |
C1—H1 | 0.960 | C15—C16 | 1.368 (10) |
C2—C3 | 1.38 (1) | C15—H15 | 0.961 |
C2—H2 | 0.960 | C16—C17 | 1.383 (9) |
C3—C4 | 1.37 (1) | C16—H16 | 0.960 |
C3—H3 | 0.960 | C17—C18 | 1.389 (8) |
C4—C5 | 1.384 (10) | C17—H17 | 0.961 |
C4—H4 | 0.960 | C18—C19 | 1.396 (8) |
C5—C6 | 1.48 (1) | C18—H18 | 0.960 |
Cu1···O3 | 3.531 (7) | O4···C13v | 3.594 (10) |
O2···C7ii | 3.242 (8) | O5···C7ii | 3.158 (10) |
O2···C3iii | 3.372 (9) | O5···C10vi | 3.465 (10) |
O2···C6 | 3.547 (9) | O5···C9vi | 3.527 (9) |
O3···C11iv | 3.308 (8) | O5···C6ii | 3.60 (1) |
O3···C6 | 3.387 (9) | C3···C9vi | 3.56 (1) |
O3···C18i | 3.441 (9) | C3···C16vi | 3.58 (1) |
O3···N1 | 3.453 (8) | C10···C17vii | 3.56 (1) |
O3···C5 | 3.487 (8) | C11···C17vii | 3.364 (10) |
O4···C12iv | 3.349 (9) | C11···C18vii | 3.446 (9) |
O4···C11iv | 3.41 (1) | C12···C17vii | 3.545 (9) |
O4···C3v | 3.57 (1) | ||
O1—Cu1—O1i | 80.4 (2) | C5—C6—H5 | 109.5 |
O1—Cu1—N1 | 105.3 (2) | C5—C6—H6 | 109.5 |
O1—Cu1—N2 | 92.3 (2) | H5—C6—H6 | 109.5 |
O1—Cu1—N3 | 98.9 (2) | N2—C7—C8 | 112.2 (5) |
O1i—Cu1—N1 | 102.5 (2) | N2—C7—H7 | 108.8 |
O1i—Cu1—N2 | 172.1 (2) | N2—C7—H8 | 108.8 |
O1i—Cu1—N3 | 94.5 (2) | C8—C7—H7 | 108.8 |
N1—Cu1—N2 | 82.3 (2) | C8—C7—H8 | 108.7 |
N1—Cu1—N3 | 152.3 (2) | H7—C7—H8 | 109.5 |
N2—Cu1—N3 | 83.5 (2) | N3—C8—C7 | 117.1 (6) |
O2—Cl1—O3 | 107.6 (5) | N3—C8—C9 | 121.6 (6) |
O2—Cl1—O4 | 110.2 (5) | C7—C8—C9 | 121.3 (5) |
O2—Cl1—O5 | 107.3 (4) | C8—C9—C10 | 119.6 (6) |
O3—Cl1—O4 | 108.4 (4) | C8—C9—H9 | 120.2 |
O3—Cl1—O5 | 110.5 (6) | C10—C9—H9 | 120.2 |
O4—Cl1—O5 | 112.7 (6) | C9—C10—C11 | 118.6 (6) |
Cu1—O1—Cu1i | 99.6 (2) | C9—C10—H10 | 120.7 |
Cu1—O1—C19 | 122.9 (3) | C11—C10—H10 | 120.6 |
Cu1i—O1—C19 | 131.5 (4) | C10—C11—C12 | 119.5 (6) |
Cu1—N1—C1 | 129.1 (4) | C10—C11—H11 | 120.3 |
Cu1—N1—C5 | 112.5 (4) | C12—C11—H11 | 120.3 |
C1—N1—C5 | 118.2 (6) | N3—C12—C11 | 122.4 (6) |
Cu1—N2—C6 | 103.4 (4) | N3—C12—H12 | 118.8 |
Cu1—N2—C7 | 112.0 (4) | C11—C12—H12 | 118.8 |
Cu1—N2—C13 | 109.8 (3) | N2—C13—C14 | 115.9 (5) |
C6—N2—C7 | 112.1 (5) | N2—C13—H13 | 107.9 |
C6—N2—C13 | 107.4 (5) | N2—C13—H14 | 107.8 |
C7—N2—C13 | 111.7 (5) | C14—C13—H13 | 107.8 |
Cu1—N3—C8 | 115.1 (4) | C14—C13—H14 | 107.8 |
Cu1—N3—C12 | 126.6 (4) | H13—C13—H14 | 109.4 |
C8—N3—C12 | 118.2 (5) | C13—C14—C15 | 119.8 (5) |
N1—C1—C2 | 123.4 (6) | C13—C14—C19 | 121.3 (5) |
N1—C1—H1 | 118.3 | C15—C14—C19 | 118.4 (6) |
C2—C1—H1 | 118.3 | C14—C15—C16 | 122.0 (5) |
C1—C2—C3 | 117.5 (7) | C14—C15—H15 | 119.0 |
C1—C2—H2 | 121.3 | C16—C15—H15 | 119.0 |
C3—C2—H2 | 121.3 | C15—C16—C17 | 119.5 (6) |
C2—C3—C4 | 120.5 (7) | C15—C16—H16 | 120.3 |
C2—C3—H3 | 119.8 | C17—C16—H16 | 120.3 |
C4—C3—H3 | 119.8 | C16—C17—C18 | 120.2 (6) |
C3—C4—C5 | 119.0 (7) | C16—C17—H17 | 119.9 |
C3—C4—H4 | 120.5 | C18—C17—H17 | 119.9 |
C5—C4—H4 | 120.5 | C17—C18—C19 | 120.8 (5) |
N1—C5—C4 | 121.5 (7) | C17—C18—H18 | 119.6 |
N1—C5—C6 | 114.8 (6) | C19—C18—H18 | 119.6 |
C4—C5—C6 | 123.7 (6) | O1—C19—C14 | 118.7 (5) |
N2—C6—C5 | 109.3 (5) | O1—C19—C18 | 122.3 (5) |
N2—C6—H5 | 109.6 | C14—C19—C18 | 118.9 (5) |
N2—C6—H6 | 109.6 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) x, y+1, z; (vii) x−1/2, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C19H18N3O)2](ClO4)2 |
Mr | 934.74 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 11.380 (1), 9.877 (2), 17.400 (2) |
β (°) | 104.79 (1) |
V (Å3) | 1891.0 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.33 |
Crystal size (mm) | 0.7 × 0.15 × 0.1 |
Data collection | |
Diffractometer | Rigaku AFC-5S diffractometer |
Absorption correction | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.662, 0.897 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4819, 4338, 2393 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.185, 0.98 |
No. of reflections | 4338 |
No. of parameters | 262 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.59, −0.63 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), TEXSAN.
Cu1—O1 | 2.203 (4) | Cu1—N2 | 2.037 (4) |
Cu1—O1i | 1.938 (3) | Cu1—N3 | 2.000 (5) |
Cu1—N1 | 2.013 (5) | ||
O1—Cu1—O1i | 80.4 (2) | Cu1—O1—Cu1i | 99.6 (2) |
Symmetry code: (i) −x+1, −y, −z+1. |
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The title copper(II) complex, [Cu2(phpy)2](ClO4)2 [phpy is (2-hydroxyphenylmethyl)bis(2-pyridylmethyl)aminate], (I), which has a long Cu–phenolic O atom bond, can be considered as a nobel model compound for galactose oxidase (Ito et al., 1998).
Adams et al. (1996) noted that the structure was difficult to refine because of a twinning problem.