The title compound, C
20H
20N
4O
4, is a potentially
N,
N′-bidentate donor ligand with two chiral C atoms. In the crystal structure, the molecules form centrosymmetric dimers
via C—H
N hydrogen bonds.
Supporting information
CCDC reference: 270554
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.093
- wR factor = 0.199
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT432_ALERT_2_C Short Inter X...Y Contact C2 .. C2 .. 3.11 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
N,
N'-Bis(3-nitrobenzylidene)-
trans-1,2-cyclohexanediamine
top
Crystal data top
C20H20N4O4 | F(000) = 1600 |
Mr = 380.40 | Dx = 1.293 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1852 reflections |
a = 19.288 (4) Å | θ = 4.3–28.4° |
b = 15.840 (3) Å | µ = 0.09 mm−1 |
c = 15.485 (3) Å | T = 298 K |
β = 124.297 (3)° | Block, white |
V = 3908.3 (13) Å3 | 0.26 × 0.21 × 0.08 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4260 independent reflections |
Radiation source: fine-focus sealed tube | 1899 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
φ and ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→24 |
Tmin = 0.976, Tmax = 0.993 | k = −19→20 |
13932 measured reflections | l = −19→18 |
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)] = 0.093 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0612P)2 + 1.3941P] where P = (Fo2 + 2Fc2)/3 |
4260 reflections | (Δ/σ)max < 0.001 |
259 parameters | Δρmax = 0.23 e Å−3 |
2 restraints | Δρmin = −0.14 e Å−3 |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1282 (2) | 0.3010 (2) | 0.7769 (2) | 0.0518 (9) | |
C2 | 0.0451 (2) | 0.3051 (2) | 0.6925 (2) | 0.0499 (9) | |
H2 | 0.0104 | 0.2581 | 0.6723 | 0.060* | |
C3 | 0.0154 (2) | 0.3796 (2) | 0.6395 (3) | 0.0592 (10) | |
C4 | 0.0643 (3) | 0.4501 (3) | 0.6659 (3) | 0.0805 (12) | |
H4 | 0.0425 | 0.4995 | 0.6273 | 0.097* | |
C5 | 0.1464 (3) | 0.4465 (3) | 0.7508 (4) | 0.0886 (14) | |
H5 | 0.1804 | 0.4941 | 0.7710 | 0.106* | |
C6 | 0.1778 (2) | 0.3725 (3) | 0.8054 (3) | 0.0691 (11) | |
H6 | 0.2334 | 0.3704 | 0.8625 | 0.083* | |
C7 | 0.1641 (2) | 0.2216 (2) | 0.8358 (2) | 0.0551 (9) | |
H7 | 0.2188 | 0.2225 | 0.8952 | 0.066* | |
C8 | 0.1687 (2) | 0.0786 (2) | 0.8732 (3) | 0.0613 (10) | |
H8 | 0.2233 (14) | 0.0974 (19) | 0.9335 (19) | 0.074* | |
C9 | 0.1186 (2) | 0.0388 (2) | 0.9103 (3) | 0.0662 (11) | |
H9 | 0.0620 (14) | 0.026 (2) | 0.8480 (19) | 0.079* | |
C10 | 0.1594 (3) | −0.0431 (3) | 0.9693 (3) | 0.0912 (14) | |
H10A | 0.1242 | −0.0692 | 0.9883 | 0.109* | |
H10B | 0.2133 | −0.0306 | 1.0332 | 0.109* | |
C11 | 0.1717 (3) | −0.1047 (3) | 0.9031 (4) | 0.0980 (15) | |
H11A | 0.2006 | −0.1546 | 0.9440 | 0.118* | |
H11B | 0.1173 | −0.1220 | 0.8430 | 0.118* | |
C12 | 0.2216 (3) | −0.0649 (3) | 0.8665 (4) | 0.0922 (14) | |
H12A | 0.2254 | −0.1039 | 0.8211 | 0.111* | |
H12B | 0.2781 | −0.0534 | 0.9263 | 0.111* | |
C13 | 0.1812 (3) | 0.0168 (2) | 0.8080 (3) | 0.0816 (12) | |
H13A | 0.1273 | 0.0043 | 0.7440 | 0.098* | |
H13B | 0.2165 | 0.0427 | 0.7890 | 0.098* | |
C14 | 0.0427 (3) | 0.1172 (2) | 0.9591 (3) | 0.0677 (11) | |
H14 | −0.0043 | 0.0933 | 0.9003 | 0.081* | |
C15 | 0.0296 (2) | 0.1763 (2) | 1.0213 (3) | 0.0614 (10) | |
C16 | 0.0971 (2) | 0.2084 (2) | 1.1145 (3) | 0.0667 (10) | |
H16 | 0.1513 | 0.1897 | 1.1415 | 0.080* | |
C17 | 0.0824 (3) | 0.2680 (3) | 1.1662 (3) | 0.0692 (11) | |
C18 | 0.0035 (3) | 0.2976 (3) | 1.1298 (4) | 0.0852 (13) | |
H18 | −0.0044 | 0.3384 | 1.1667 | 0.102* | |
C19 | −0.0630 (3) | 0.2656 (3) | 1.0381 (4) | 0.0930 (14) | |
H19 | −0.1171 | 0.2846 | 1.0120 | 0.112* | |
C20 | −0.0504 (3) | 0.2052 (3) | 0.9842 (3) | 0.0770 (12) | |
H20 | −0.0961 | 0.1835 | 0.9222 | 0.092* | |
N1 | −0.0727 (2) | 0.3833 (3) | 0.5472 (3) | 0.0805 (11) | |
N2 | 0.12501 (17) | 0.15320 (19) | 0.8101 (2) | 0.0601 (8) | |
N3 | 0.1136 (2) | 0.09676 (18) | 0.9804 (2) | 0.0647 (9) | |
N4 | 0.1545 (3) | 0.3023 (3) | 1.2646 (3) | 0.0897 (11) | |
O1 | −0.0955 (2) | 0.4457 (3) | 0.4945 (3) | 0.1661 (19) | |
O2 | −0.11755 (18) | 0.3236 (2) | 0.5294 (2) | 0.0851 (9) | |
O3 | 0.2249 (2) | 0.2839 (2) | 1.2909 (3) | 0.1213 (13) | |
O4 | 0.1402 (2) | 0.3495 (2) | 1.3158 (3) | 0.1207 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.050 (2) | 0.057 (2) | 0.049 (2) | 0.0043 (19) | 0.0279 (18) | 0.0007 (18) |
C2 | 0.050 (2) | 0.053 (2) | 0.051 (2) | 0.0035 (17) | 0.0312 (18) | −0.0024 (17) |
C3 | 0.059 (3) | 0.062 (3) | 0.062 (2) | 0.010 (2) | 0.037 (2) | 0.010 (2) |
C4 | 0.083 (3) | 0.065 (3) | 0.095 (3) | 0.016 (2) | 0.052 (3) | 0.024 (2) |
C5 | 0.087 (4) | 0.060 (3) | 0.112 (4) | −0.009 (2) | 0.051 (3) | 0.003 (3) |
C6 | 0.051 (2) | 0.072 (3) | 0.071 (3) | −0.006 (2) | 0.026 (2) | −0.008 (2) |
C7 | 0.041 (2) | 0.067 (3) | 0.0432 (19) | 0.0051 (19) | 0.0149 (16) | −0.0025 (18) |
C8 | 0.046 (2) | 0.056 (2) | 0.063 (2) | 0.0050 (19) | 0.0192 (19) | 0.005 (2) |
C9 | 0.061 (3) | 0.062 (3) | 0.061 (2) | −0.008 (2) | 0.025 (2) | −0.006 (2) |
C10 | 0.110 (4) | 0.065 (3) | 0.087 (3) | −0.012 (2) | 0.049 (3) | 0.003 (2) |
C11 | 0.112 (4) | 0.058 (3) | 0.100 (3) | 0.002 (3) | 0.045 (3) | −0.004 (3) |
C12 | 0.086 (3) | 0.067 (3) | 0.106 (4) | 0.008 (3) | 0.044 (3) | −0.003 (3) |
C13 | 0.082 (3) | 0.070 (3) | 0.088 (3) | 0.011 (2) | 0.045 (3) | 0.000 (2) |
C14 | 0.057 (3) | 0.075 (3) | 0.056 (2) | −0.010 (2) | 0.023 (2) | 0.003 (2) |
C15 | 0.051 (3) | 0.074 (3) | 0.052 (2) | 0.000 (2) | 0.025 (2) | 0.013 (2) |
C16 | 0.065 (3) | 0.073 (3) | 0.059 (2) | 0.000 (2) | 0.033 (2) | 0.010 (2) |
C17 | 0.074 (3) | 0.072 (3) | 0.066 (3) | −0.003 (2) | 0.042 (2) | 0.013 (2) |
C18 | 0.103 (4) | 0.088 (3) | 0.086 (3) | 0.009 (3) | 0.066 (3) | 0.012 (3) |
C19 | 0.076 (3) | 0.124 (4) | 0.092 (4) | 0.019 (3) | 0.055 (3) | 0.027 (3) |
C20 | 0.064 (3) | 0.100 (3) | 0.067 (3) | −0.004 (2) | 0.037 (2) | 0.015 (3) |
N1 | 0.064 (3) | 0.091 (3) | 0.085 (3) | 0.026 (2) | 0.041 (2) | 0.035 (2) |
N2 | 0.0498 (19) | 0.058 (2) | 0.0559 (18) | 0.0036 (16) | 0.0194 (15) | 0.0013 (15) |
N3 | 0.055 (2) | 0.062 (2) | 0.060 (2) | −0.0013 (16) | 0.0221 (17) | 0.0002 (16) |
N4 | 0.098 (3) | 0.088 (3) | 0.082 (3) | −0.016 (3) | 0.049 (3) | −0.007 (2) |
O1 | 0.100 (3) | 0.157 (3) | 0.184 (4) | 0.041 (2) | 0.046 (3) | 0.119 (3) |
O2 | 0.061 (2) | 0.103 (2) | 0.0713 (19) | 0.0139 (17) | 0.0250 (16) | 0.0112 (17) |
O3 | 0.083 (3) | 0.148 (3) | 0.101 (2) | −0.019 (2) | 0.032 (2) | −0.036 (2) |
O4 | 0.147 (3) | 0.112 (3) | 0.114 (3) | −0.028 (2) | 0.080 (3) | −0.041 (2) |
Geometric parameters (Å, º) top
C1—C6 | 1.385 (4) | C11—H11A | 0.9700 |
C1—C2 | 1.386 (4) | C11—H11B | 0.9700 |
C1—C7 | 1.477 (4) | C12—C13 | 1.518 (5) |
C2—C3 | 1.365 (4) | C12—H12A | 0.9700 |
C2—H2 | 0.9300 | C12—H12B | 0.9700 |
C3—C4 | 1.368 (5) | C13—H13A | 0.9700 |
C3—N1 | 1.482 (5) | C13—H13B | 0.9700 |
C4—C5 | 1.375 (5) | C14—N3 | 1.254 (4) |
C4—H4 | 0.9300 | C14—C15 | 1.463 (5) |
C5—C6 | 1.370 (5) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—C20 | 1.386 (5) |
C6—H6 | 0.9300 | C15—C16 | 1.385 (5) |
C7—N2 | 1.250 (4) | C16—C17 | 1.366 (5) |
C7—H7 | 0.9300 | C16—H16 | 0.9300 |
C8—N2 | 1.460 (4) | C17—C18 | 1.374 (5) |
C8—C9 | 1.512 (5) | C17—N4 | 1.471 (5) |
C8—C13 | 1.521 (5) | C18—C19 | 1.366 (6) |
C8—H8 | 0.981 (18) | C18—H18 | 0.9300 |
C9—N3 | 1.466 (5) | C19—C20 | 1.379 (6) |
C9—C10 | 1.526 (5) | C19—H19 | 0.9300 |
C9—H9 | 0.987 (18) | C20—H20 | 0.9300 |
C10—C11 | 1.527 (5) | N1—O1 | 1.197 (4) |
C10—H10A | 0.9700 | N1—O2 | 1.203 (4) |
C10—H10B | 0.9700 | N4—O3 | 1.213 (4) |
C11—C12 | 1.503 (6) | N4—O4 | 1.228 (4) |
| | | |
C6—C1—C2 | 119.1 (3) | C10—C11—H11B | 109.4 |
C6—C1—C7 | 120.1 (3) | H11A—C11—H11B | 108.0 |
C2—C1—C7 | 120.9 (3) | C11—C12—C13 | 111.1 (4) |
C3—C2—C1 | 118.6 (3) | C11—C12—H12A | 109.4 |
C3—C2—H2 | 120.7 | C13—C12—H12A | 109.4 |
C1—C2—H2 | 120.7 | C11—C12—H12B | 109.4 |
C2—C3—C4 | 122.8 (4) | C13—C12—H12B | 109.4 |
C2—C3—N1 | 118.6 (4) | H12A—C12—H12B | 108.0 |
C4—C3—N1 | 118.6 (4) | C12—C13—C8 | 111.8 (3) |
C3—C4—C5 | 118.7 (4) | C12—C13—H13A | 109.2 |
C3—C4—H4 | 120.7 | C8—C13—H13A | 109.2 |
C5—C4—H4 | 120.7 | C12—C13—H13B | 109.2 |
C6—C5—C4 | 119.8 (4) | C8—C13—H13B | 109.2 |
C6—C5—H5 | 120.1 | H13A—C13—H13B | 107.9 |
C4—C5—H5 | 120.1 | N3—C14—C15 | 124.0 (4) |
C5—C6—C1 | 121.1 (4) | N3—C14—H14 | 118.0 |
C5—C6—H6 | 119.4 | C15—C14—H14 | 118.0 |
C1—C6—H6 | 119.4 | C20—C15—C16 | 118.8 (4) |
N2—C7—C1 | 123.6 (3) | C20—C15—C14 | 120.3 (4) |
N2—C7—H7 | 118.2 | C16—C15—C14 | 120.8 (4) |
C1—C7—H7 | 118.2 | C17—C16—C15 | 118.8 (4) |
N2—C8—C9 | 109.9 (3) | C17—C16—H16 | 120.6 |
N2—C8—C13 | 108.9 (3) | C15—C16—H16 | 120.6 |
C9—C8—C13 | 111.0 (3) | C16—C17—C18 | 122.9 (4) |
N2—C8—H8 | 107.3 (19) | C16—C17—N4 | 118.4 (4) |
C9—C8—H8 | 109.8 (19) | C18—C17—N4 | 118.7 (5) |
C13—C8—H8 | 109.8 (19) | C19—C18—C17 | 118.3 (4) |
N3—C9—C8 | 110.1 (3) | C19—C18—H18 | 120.8 |
N3—C9—C10 | 108.4 (3) | C17—C18—H18 | 120.8 |
C8—C9—C10 | 111.0 (3) | C18—C19—C20 | 120.2 (4) |
N3—C9—H9 | 111 (2) | C18—C19—H19 | 119.9 |
C8—C9—H9 | 107.8 (19) | C20—C19—H19 | 119.9 |
C10—C9—H9 | 108.8 (19) | C19—C20—C15 | 121.0 (4) |
C9—C10—C11 | 111.3 (3) | C19—C20—H20 | 119.5 |
C9—C10—H10A | 109.4 | C15—C20—H20 | 119.5 |
C11—C10—H10A | 109.4 | O1—N1—O2 | 123.5 (4) |
C9—C10—H10B | 109.4 | O1—N1—C3 | 118.1 (4) |
C11—C10—H10B | 109.4 | O2—N1—C3 | 118.4 (3) |
H10A—C10—H10B | 108.0 | C7—N2—C8 | 118.1 (3) |
C12—C11—C10 | 111.1 (4) | C14—N3—C9 | 118.9 (3) |
C12—C11—H11A | 109.4 | O3—N4—O4 | 123.1 (4) |
C10—C11—H11A | 109.4 | O3—N4—C17 | 119.0 (4) |
C12—C11—H11B | 109.4 | O4—N4—C17 | 118.0 (5) |
| | | |
C6—C1—C2—C3 | 0.8 (5) | C20—C15—C16—C17 | −0.7 (5) |
C7—C1—C2—C3 | −178.9 (3) | C14—C15—C16—C17 | 175.3 (3) |
C1—C2—C3—C4 | 0.4 (5) | C15—C16—C17—C18 | 0.2 (6) |
C1—C2—C3—N1 | 178.1 (3) | C15—C16—C17—N4 | −179.4 (3) |
C2—C3—C4—C5 | −1.5 (6) | C16—C17—C18—C19 | 0.2 (6) |
N1—C3—C4—C5 | −179.2 (4) | N4—C17—C18—C19 | 179.8 (4) |
C3—C4—C5—C6 | 1.4 (6) | C17—C18—C19—C20 | −0.1 (6) |
C4—C5—C6—C1 | −0.2 (6) | C18—C19—C20—C15 | −0.4 (6) |
C2—C1—C6—C5 | −0.9 (5) | C16—C15—C20—C19 | 0.8 (6) |
C7—C1—C6—C5 | 178.8 (3) | C14—C15—C20—C19 | −175.2 (4) |
C6—C1—C7—N2 | −174.7 (3) | C2—C3—N1—O1 | −171.9 (4) |
C2—C1—C7—N2 | 4.9 (5) | C4—C3—N1—O1 | 6.0 (6) |
N2—C8—C9—N3 | −64.4 (4) | C2—C3—N1—O2 | 8.4 (5) |
C13—C8—C9—N3 | 175.0 (3) | C4—C3—N1—O2 | −173.8 (4) |
N2—C8—C9—C10 | 175.6 (3) | C1—C7—N2—C8 | 178.1 (3) |
C13—C8—C9—C10 | 55.0 (4) | C9—C8—N2—C7 | 125.4 (4) |
N3—C9—C10—C11 | −176.5 (3) | C13—C8—N2—C7 | −112.8 (4) |
C8—C9—C10—C11 | −55.4 (5) | C15—C14—N3—C9 | −178.1 (3) |
C9—C10—C11—C12 | 55.7 (5) | C8—C9—N3—C14 | 124.2 (4) |
C10—C11—C12—C13 | −55.4 (5) | C10—C9—N3—C14 | −114.2 (4) |
C11—C12—C13—C8 | 55.6 (5) | C16—C17—N4—O3 | 8.0 (6) |
N2—C8—C13—C12 | −176.5 (3) | C18—C17—N4—O3 | −171.6 (4) |
C9—C8—C13—C12 | −55.3 (4) | C16—C17—N4—O4 | −172.9 (4) |
N3—C14—C15—C20 | 170.3 (4) | C18—C17—N4—O4 | 7.5 (5) |
N3—C14—C15—C16 | −5.6 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···N3i | 0.93 | 2.61 | 3.520 (5) | 166 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+2. |