Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400618X/hg6025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680400618X/hg6025Isup2.hkl |
CCDC reference: 238651
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.055
- wR factor = 0.129
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O18 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O20 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O24 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Cu PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N19 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N23 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 2451 Count of symmetry unique reflns 1998 Completeness (_total/calc) 122.67% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 453 Fraction of Friedel pairs measured 0.227 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Cu(NO3)2(C15H26N2)] | F(000) = 884 |
Mr = 421.94 | Dx = 1.59 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 40 reflections |
a = 8.4920 (15) Å | θ = 6.0–12.8° |
b = 12.241 (2) Å | µ = 1.28 mm−1 |
c = 16.961 (3) Å | T = 293 K |
V = 1763.1 (5) Å3 | Block, blue |
Z = 4 | 0.38 × 0.34 × 0.28 mm |
Bruker P4 diffractometer | Rint = 0.040 |
2θ/ω scans | θmax = 26°, θmin = 2.1° |
Absorption correction: psi scan (North et al., 1968) | h = −1→10 |
Tmin = 0.620, Tmax = 0.697 | k = −15→1 |
2632 measured reflections | l = −20→1 |
2451 independent reflections | 3 standard reflections every 97 reflections |
1263 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.055 | (Δ/σ)max < 0.001 |
wR(F2) = 0.129 | Δρmax = 0.49 e Å−3 |
S = 0.97 | Δρmin = −0.53 e Å−3 |
2451 reflections | Absolute structure: Flack (1983), 453 Friedel pairs |
233 parameters | Absolute structure parameter: −0.03 (4) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cu | 0.08213 (14) | 0.07445 (9) | 0.34154 (7) | 0.0387 (3) | |
N1 | 0.1426 (8) | −0.0692 (7) | 0.3959 (4) | 0.0347 (17) | |
C2 | 0.0206 (12) | −0.1567 (7) | 0.3838 (5) | 0.045 (3) | |
H2A | 0.0026 | −0.1662 | 0.3278 | 0.055* | |
H2B | 0.0602 | −0.2252 | 0.4046 | 0.055* | |
C3 | −0.1326 (12) | −0.1300 (9) | 0.4233 (6) | 0.057 (3) | |
H3A | −0.2055 | −0.1901 | 0.4158 | 0.069* | |
H3B | −0.1778 | −0.0656 | 0.3988 | 0.069* | |
C4 | −0.1116 (12) | −0.1092 (9) | 0.5114 (6) | 0.064 (3) | |
H4A | −0.0794 | −0.1759 | 0.5376 | 0.076* | |
H4B | −0.2104 | −0.0852 | 0.5342 | 0.076* | |
C5 | 0.0138 (12) | −0.0212 (8) | 0.5225 (5) | 0.051 (3) | |
H5A | 0.0315 | −0.0097 | 0.5784 | 0.061* | |
H5B | −0.0232 | 0.047 | 0.5 | 0.061* | |
C6 | 0.1685 (11) | −0.0541 (8) | 0.4831 (5) | 0.040 (3) | |
H6 | 0.1973 | −0.1257 | 0.5044 | 0.048* | |
C7 | 0.3091 (13) | 0.0229 (8) | 0.4989 (5) | 0.048 (3) | |
H7 | 0.3203 | 0.0298 | 0.5562 | 0.058* | |
C8 | 0.4334 (12) | −0.0370 (7) | 0.3780 (5) | 0.048 (3) | |
H8 | 0.5262 | −0.0724 | 0.355 | 0.058* | |
N9 | 0.2860 (9) | 0.1409 (6) | 0.3774 (4) | 0.041 (2) | |
C10 | 0.3059 (13) | 0.2576 (7) | 0.3516 (7) | 0.055 (3) | |
H10A | 0.4039 | 0.2859 | 0.3728 | 0.066* | |
H10B | 0.2205 | 0.3011 | 0.3731 | 0.066* | |
C11 | 0.3073 (14) | 0.2691 (8) | 0.2626 (6) | 0.063 (3) | |
H11A | 0.2074 | 0.2448 | 0.2412 | 0.076* | |
H11B | 0.3218 | 0.3452 | 0.2484 | 0.076* | |
C12 | 0.4394 (15) | 0.2014 (8) | 0.2284 (6) | 0.066 (3) | |
H12A | 0.4319 | 0.2025 | 0.1713 | 0.08* | |
H12B | 0.5394 | 0.234 | 0.243 | 0.08* | |
C13 | 0.4361 (13) | 0.0847 (7) | 0.2563 (5) | 0.054 (3) | |
H13A | 0.5307 | 0.0474 | 0.2389 | 0.064* | |
H13B | 0.3461 | 0.0475 | 0.2336 | 0.064* | |
C14 | 0.4259 (11) | 0.0800 (7) | 0.3460 (5) | 0.049 (2) | |
H14 | 0.5194 | 0.1177 | 0.3661 | 0.058* | |
C15 | 0.2923 (10) | −0.1060 (7) | 0.3586 (5) | 0.043 (3) | |
H15A | 0.2783 | −0.1064 | 0.3018 | 0.052* | |
H15B | 0.3133 | −0.1805 | 0.3749 | 0.052* | |
C16 | 0.2878 (14) | 0.1364 (7) | 0.4661 (5) | 0.049 (3) | |
H16A | 0.1896 | 0.1661 | 0.4858 | 0.058* | |
H16B | 0.3725 | 0.1824 | 0.4853 | 0.058* | |
C17 | 0.4570 (11) | −0.0322 (9) | 0.4681 (5) | 0.056 (3) | |
H17A | 0.4679 | −0.1051 | 0.49 | 0.067* | |
H17B | 0.55 | 0.01 | 0.4814 | 0.067* | |
O18 | −0.0226 (10) | 0.2200 (6) | 0.3219 (5) | 0.071 (3) | |
N19 | −0.1448 (12) | 0.2251 (8) | 0.3592 (5) | 0.054 (3) | |
O20 | −0.1767 (9) | 0.1549 (7) | 0.4089 (5) | 0.074 (2) | |
O21 | −0.2419 (10) | 0.3004 (6) | 0.3452 (5) | 0.089 (3) | |
O22 | −0.0798 (10) | 0.0075 (5) | 0.2734 (4) | 0.0628 (19) | |
N23 | −0.0562 (14) | 0.0304 (7) | 0.2016 (6) | 0.065 (3) | |
O24 | 0.0719 (11) | 0.0725 (6) | 0.1862 (4) | 0.077 (2) | |
O25 | −0.1552 (11) | 0.0098 (8) | 0.1523 (5) | 0.107 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0435 (6) | 0.0346 (5) | 0.0380 (5) | 0.0034 (7) | 0.0003 (7) | 0.0020 (7) |
N1 | 0.041 (4) | 0.036 (4) | 0.027 (3) | 0.005 (5) | −0.009 (3) | −0.003 (4) |
C2 | 0.062 (7) | 0.036 (5) | 0.038 (5) | −0.008 (6) | −0.006 (6) | −0.013 (5) |
C3 | 0.061 (8) | 0.046 (6) | 0.065 (7) | −0.002 (6) | 0.003 (6) | 0.016 (6) |
C4 | 0.051 (7) | 0.084 (8) | 0.056 (7) | 0.007 (7) | 0.004 (6) | 0.020 (6) |
C5 | 0.071 (7) | 0.048 (6) | 0.032 (5) | 0.011 (7) | 0.005 (5) | 0.005 (5) |
C6 | 0.052 (6) | 0.041 (6) | 0.028 (5) | −0.001 (6) | −0.007 (5) | 0.001 (5) |
C7 | 0.074 (8) | 0.040 (6) | 0.030 (5) | −0.003 (6) | −0.007 (6) | 0.004 (5) |
C8 | 0.030 (5) | 0.054 (6) | 0.062 (6) | 0.007 (6) | 0.004 (6) | 0.004 (5) |
N9 | 0.051 (5) | 0.034 (4) | 0.038 (4) | 0.001 (5) | 0.000 (4) | 0.003 (4) |
C10 | 0.060 (7) | 0.033 (5) | 0.073 (8) | −0.014 (6) | 0.015 (8) | 0.000 (6) |
C11 | 0.086 (9) | 0.052 (7) | 0.052 (7) | −0.014 (7) | 0.000 (7) | 0.019 (6) |
C12 | 0.070 (8) | 0.073 (7) | 0.056 (7) | −0.017 (8) | 0.018 (8) | 0.019 (6) |
C13 | 0.054 (6) | 0.061 (6) | 0.046 (5) | 0.011 (8) | 0.020 (6) | 0.009 (6) |
C14 | 0.034 (5) | 0.053 (5) | 0.059 (5) | −0.007 (8) | 0.004 (7) | 0.012 (7) |
C15 | 0.054 (7) | 0.041 (6) | 0.036 (6) | 0.013 (5) | 0.003 (5) | −0.004 (5) |
C16 | 0.067 (8) | 0.043 (6) | 0.036 (6) | −0.006 (7) | −0.002 (6) | −0.004 (5) |
C17 | 0.050 (7) | 0.069 (7) | 0.048 (6) | 0.016 (6) | −0.016 (5) | −0.002 (6) |
O18 | 0.057 (5) | 0.053 (5) | 0.103 (7) | 0.003 (5) | 0.010 (5) | 0.009 (5) |
N19 | 0.081 (8) | 0.037 (5) | 0.043 (6) | −0.013 (6) | 0.001 (6) | 0.002 (5) |
O20 | 0.05 | 0.092 (6) | 0.081 (6) | 0.010 (5) | 0.003 (5) | −0.004 (5) |
O21 | 0.095 (6) | 0.069 (5) | 0.103 (6) | 0.037 (6) | −0.021 (7) | −0.005 (6) |
O22 | 0.088 (5) | 0.055 (4) | 0.045 (4) | −0.014 (5) | −0.016 (5) | 0.017 (4) |
N23 | 0.082 (8) | 0.049 (5) | 0.065 (7) | −0.021 (6) | −0.015 (7) | 0.012 (5) |
O24 | 0.092 (5) | 0.065 | 0.073 (5) | −0.009 (7) | 0.027 (5) | −0.021 (5) |
O25 | 0.123 (8) | 0.131 (8) | 0.067 (6) | −0.030 (7) | −0.038 (6) | 0.019 (6) |
Cu—O22 | 1.974 (7) | C8—H8 | 0.98 |
Cu—N9 | 2.007 (8) | N9—C14 | 1.501 (11) |
Cu—O18 | 2.019 (8) | N9—C10 | 1.504 (10) |
Cu—N1 | 2.051 (8) | N9—C16 | 1.506 (10) |
Cu—O24 | 2.636 (7) | C10—C11 | 1.516 (15) |
Cu—O20 | 2.665 (7) | C10—H10A | 0.97 |
N1—C15 | 1.490 (10) | C10—H10B | 0.97 |
N1—C2 | 1.504 (10) | C11—C12 | 1.511 (14) |
N1—C6 | 1.507 (9) | C11—H11A | 0.97 |
C2—C3 | 1.499 (12) | C11—H11B | 0.97 |
C2—H2A | 0.97 | C12—C13 | 1.505 (12) |
C2—H2B | 0.97 | C12—H12A | 0.97 |
C3—C4 | 1.525 (13) | C12—H12B | 0.97 |
C3—H3A | 0.97 | C13—C14 | 1.524 (11) |
C3—H3B | 0.97 | C13—H13A | 0.97 |
C4—C5 | 1.526 (12) | C13—H13B | 0.97 |
C4—H4A | 0.97 | C14—H14 | 0.98 |
C4—H4B | 0.97 | C15—H15A | 0.97 |
C5—C6 | 1.528 (11) | C15—H15B | 0.97 |
C5—H5A | 0.97 | C16—H16A | 0.97 |
C5—H5B | 0.97 | C16—H16B | 0.97 |
C6—C7 | 1.545 (12) | C17—H17A | 0.97 |
C6—H6 | 0.98 | C17—H17B | 0.97 |
C7—C16 | 1.507 (12) | O18—N19 | 1.216 (7) |
C7—C17 | 1.519 (12) | N19—O20 | 1.234 (10) |
C7—H7 | 0.98 | N19—O21 | 1.259 (11) |
C8—C15 | 1.502 (12) | O22—N23 | 1.266 (10) |
C8—C14 | 1.533 (12) | N23—O25 | 1.212 (11) |
C8—C17 | 1.544 (11) | N23—O24 | 1.231 (11) |
O22—Cu—N9 | 161.2 (3) | C14—N9—C16 | 109.1 (8) |
O22—Cu—O18 | 87.9 (3) | C10—N9—C16 | 108.9 (7) |
N9—Cu—O18 | 94.2 (3) | C14—N9—Cu | 112.0 (5) |
O22—Cu—N1 | 94.7 (3) | C10—N9—Cu | 113.2 (6) |
N9—Cu—N1 | 89.7 (3) | C16—N9—Cu | 107.3 (6) |
O18—Cu—N1 | 160.2 (3) | N9—C10—C11 | 112.2 (8) |
O22—Cu—O24 | 52.3 (3) | N9—C10—H10A | 109.2 |
N9—Cu—O24 | 109.6 (3) | C11—C10—H10A | 109.2 |
O18—Cu—O24 | 80.1 (3) | N9—C10—H10B | 109.2 |
N1—Cu—O24 | 116.7 (3) | C11—C10—H10B | 109.2 |
O22—Cu—O20 | 80.2 (3) | H10A—C10—H10B | 107.9 |
N9—Cu—O20 | 115.6 (3) | C12—C11—C10 | 109.7 (9) |
O18—Cu—O20 | 51.8 (3) | C12—C11—H11A | 109.7 |
N1—Cu—O20 | 109.3 (3) | C10—C11—H11A | 109.7 |
O24—Cu—O20 | 113.8 (3) | C12—C11—H11B | 109.7 |
C15—N1—C2 | 108.3 (7) | C10—C11—H11B | 109.7 |
C15—N1—C6 | 109.3 (6) | H11A—C11—H11B | 108.2 |
C2—N1—C6 | 108.8 (7) | C13—C12—C11 | 112.7 (9) |
C15—N1—Cu | 106.3 (5) | C13—C12—H12A | 109 |
C2—N1—Cu | 112.1 (5) | C11—C12—H12A | 109 |
C6—N1—Cu | 111.9 (6) | C13—C12—H12B | 109 |
C3—C2—N1 | 112.4 (7) | C11—C12—H12B | 109 |
C3—C2—H2A | 109.1 | H12A—C12—H12B | 107.8 |
N1—C2—H2A | 109.1 | C12—C13—C14 | 110.5 (8) |
C3—C2—H2B | 109.1 | C12—C13—H13A | 109.5 |
N1—C2—H2B | 109.1 | C14—C13—H13A | 109.5 |
H2A—C2—H2B | 107.9 | C12—C13—H13B | 109.5 |
C2—C3—C4 | 111.9 (8) | C14—C13—H13B | 109.5 |
C2—C3—H3A | 109.2 | H13A—C13—H13B | 108.1 |
C4—C3—H3A | 109.2 | N9—C14—C13 | 112.4 (8) |
C2—C3—H3B | 109.2 | N9—C14—C8 | 111.8 (8) |
C4—C3—H3B | 109.2 | C13—C14—C8 | 112.7 (8) |
H3A—C3—H3B | 107.9 | N9—C14—H14 | 106.5 |
C3—C4—C5 | 108.7 (8) | C13—C14—H14 | 106.5 |
C3—C4—H4A | 109.9 | C8—C14—H14 | 106.5 |
C5—C4—H4A | 109.9 | N1—C15—C8 | 114.7 (7) |
C3—C4—H4B | 109.9 | N1—C15—H15A | 108.6 |
C5—C4—H4B | 109.9 | C8—C15—H15A | 108.6 |
H4A—C4—H4B | 108.3 | N1—C15—H15B | 108.6 |
C4—C5—C6 | 111.1 (8) | C8—C15—H15B | 108.6 |
C4—C5—H5A | 109.4 | H15A—C15—H15B | 107.6 |
C6—C5—H5A | 109.4 | N9—C16—C7 | 113.9 (8) |
C4—C5—H5B | 109.4 | N9—C16—H16A | 108.8 |
C6—C5—H5B | 109.4 | C7—C16—H16A | 108.8 |
H5A—C5—H5B | 108 | N9—C16—H16B | 108.8 |
N1—C6—C5 | 109.7 (7) | C7—C16—H16B | 108.8 |
N1—C6—C7 | 111.0 (7) | H16A—C16—H16B | 107.7 |
C5—C6—C7 | 115.3 (8) | C7—C17—C8 | 104.5 (8) |
N1—C6—H6 | 106.8 | C7—C17—H17A | 110.9 |
C5—C6—H6 | 106.8 | C8—C17—H17A | 110.9 |
C7—C6—H6 | 106.8 | C7—C17—H17B | 110.9 |
C16—C7—C17 | 112.5 (9) | C8—C17—H17B | 110.9 |
C16—C7—C6 | 113.9 (9) | H17A—C17—H17B | 108.9 |
C17—C7—C6 | 107.9 (7) | N19—O18—Cu | 109.6 (8) |
C16—C7—H7 | 107.4 | O18—N19—O20 | 120.4 (11) |
C17—C7—H7 | 107.4 | O18—N19—O21 | 119.9 (10) |
C6—C7—H7 | 107.4 | O20—N19—O21 | 119.6 (10) |
C15—C8—C14 | 114.5 (8) | N19—O20—Cu | 77.5 (6) |
C15—C8—C17 | 110.0 (8) | N23—O22—Cu | 111.1 (7) |
C14—C8—C17 | 108.7 (8) | O25—N23—O24 | 123.6 (11) |
C15—C8—H8 | 107.8 | O25—N23—O22 | 120.5 (11) |
C14—C8—H8 | 107.8 | O24—N23—O22 | 115.9 (10) |
C17—C8—H8 | 107.8 | N23—O24—Cu | 79.7 (6) |
C14—N9—C10 | 106.3 (7) |
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