In the title compound, C
19H
26N
2O
4, the molecules are linked into sheets
via C—H
O, N—H
O and O—H
N hydrogen bonds. There are no significant intermolecular interactions between adjacent sheets.
Supporting information
CCDC reference: 633880
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.152
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT416_ALERT_2_B Short Intra D-H..H-D H1 .. H1A .. 1.62 Ang.
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B .. O3 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19B .. O1 .. 2.69 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.
6,6'-Dimethoxy-2,2'-(propane-1,3-diyldiiminodimethylene)diphenol
top
Crystal data top
C19H26N2O4 | Z = 2 |
Mr = 346.42 | F(000) = 372 |
Triclinic, P1 | Dx = 1.231 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.278 (3) Å | Cell parameters from 1431 reflections |
b = 10.013 (4) Å | θ = 2.6–23.4° |
c = 10.816 (4) Å | µ = 0.09 mm−1 |
α = 92.144 (4)° | T = 298 K |
β = 98.550 (4)° | Block, colourless |
γ = 109.215 (4)° | 0.23 × 0.21 × 0.17 mm |
V = 934.2 (6) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3234 independent reflections |
Radiation source: fine-focus sealed tube | 2033 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.980, Tmax = 0.985 | k = −11→11 |
4873 measured reflections | l = −9→12 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0655P)2 + 0.3501P] where P = (Fo2 + 2Fc2)/3 |
3234 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.42 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 | |
N1 | 0.5429 (2) | 0.3083 (2) | 0.7352 (2) | 0.0434 (6) | |
H1 | 0.4847 | 0.3582 | 0.7010 | 0.052* | |
N2 | 0.6656 (3) | 0.2540 (2) | 0.3172 (2) | 0.0461 (6) | |
H2 | 0.6224 | 0.3182 | 0.2899 | 0.055* | |
O1 | 0.4798 (2) | 0.57229 (18) | 0.78904 (18) | 0.0538 (6) | |
H1A | 0.4485 | 0.4859 | 0.7725 | 0.081* | |
O2 | 0.6192 (2) | 0.84603 (17) | 0.87303 (19) | 0.0549 (6) | |
O3 | 0.6375 (2) | −0.03760 (18) | 0.2664 (2) | 0.0575 (6) | |
H3 | 0.6053 | −0.1225 | 0.2763 | 0.086* | |
O4 | 0.7913 (2) | −0.21618 (19) | 0.3306 (2) | 0.0653 (6) | |
C1 | 0.6801 (3) | 0.5094 (3) | 0.9070 (2) | 0.0414 (6) | |
C2 | 0.8218 (3) | 0.5515 (3) | 0.9865 (3) | 0.0539 (8) | |
H2A | 0.8656 | 0.4837 | 1.0119 | 0.065* | |
C3 | 0.8984 (4) | 0.6914 (3) | 1.0284 (3) | 0.0617 (9) | |
H3A | 0.9941 | 0.7177 | 1.0809 | 0.074* | |
C4 | 0.8345 (3) | 0.7936 (3) | 0.9932 (3) | 0.0526 (7) | |
H4 | 0.8859 | 0.8882 | 1.0233 | 0.063* | |
C5 | 0.6951 (3) | 0.7550 (3) | 0.9138 (2) | 0.0404 (6) | |
C6 | 0.6170 (3) | 0.6126 (3) | 0.8682 (2) | 0.0384 (6) | |
C7 | 0.6853 (4) | 0.9906 (3) | 0.9214 (4) | 0.0757 (11) | |
H7A | 0.6962 | 0.9972 | 1.0113 | 0.114* | |
H7B | 0.6193 | 1.0416 | 0.8879 | 0.114* | |
H7C | 0.7853 | 1.0310 | 0.8976 | 0.114* | |
C8 | 0.5890 (3) | 0.3544 (3) | 0.8697 (3) | 0.0496 (7) | |
H8A | 0.6501 | 0.2993 | 0.9068 | 0.060* | |
H8B | 0.4959 | 0.3305 | 0.9070 | 0.060* | |
C9 | 0.6695 (3) | 0.3269 (3) | 0.6657 (3) | 0.0476 (7) | |
H9A | 0.7275 | 0.2661 | 0.6950 | 0.057* | |
H9B | 0.7390 | 0.4246 | 0.6808 | 0.057* | |
C10 | 0.6095 (3) | 0.2909 (3) | 0.5272 (3) | 0.0521 (7) | |
H10A | 0.5313 | 0.1970 | 0.5141 | 0.062* | |
H10B | 0.5599 | 0.3579 | 0.4975 | 0.062* | |
C11 | 0.7320 (3) | 0.2934 (3) | 0.4498 (2) | 0.0462 (7) | |
H11A | 0.8089 | 0.3879 | 0.4599 | 0.055* | |
H11B | 0.7836 | 0.2278 | 0.4797 | 0.055* | |
C12 | 0.7793 (4) | 0.2488 (3) | 0.2374 (3) | 0.0512 (7) | |
H12A | 0.8516 | 0.3443 | 0.2377 | 0.061* | |
H12B | 0.7251 | 0.2181 | 0.1519 | 0.061* | |
C13 | 0.8707 (3) | 0.1521 (3) | 0.2756 (2) | 0.0448 (7) | |
C14 | 0.7943 (3) | 0.0104 (3) | 0.2882 (2) | 0.0428 (7) | |
C15 | 0.8792 (3) | −0.0786 (3) | 0.3226 (3) | 0.0467 (7) | |
C16 | 1.0385 (3) | −0.0260 (3) | 0.3445 (3) | 0.0579 (8) | |
H16 | 1.0948 | −0.0852 | 0.3682 | 0.069* | |
C17 | 1.1138 (4) | 0.1147 (4) | 0.3310 (3) | 0.0659 (9) | |
H17 | 1.2214 | 0.1506 | 0.3451 | 0.079* | |
C18 | 1.0312 (4) | 0.2022 (3) | 0.2968 (3) | 0.0584 (8) | |
H18 | 1.0838 | 0.2970 | 0.2877 | 0.070* | |
C19 | 0.8654 (4) | −0.3170 (3) | 0.3612 (3) | 0.0738 (10) | |
H19A | 0.9359 | −0.3156 | 0.3043 | 0.111* | |
H19B | 0.7889 | −0.4100 | 0.3545 | 0.111* | |
H19C | 0.9216 | −0.2933 | 0.4456 | 0.111* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0469 (13) | 0.0374 (12) | 0.0499 (14) | 0.0183 (10) | 0.0117 (11) | 0.0037 (10) |
N2 | 0.0605 (14) | 0.0432 (13) | 0.0416 (14) | 0.0308 (11) | 0.0005 (11) | 0.0031 (10) |
O1 | 0.0514 (11) | 0.0326 (10) | 0.0689 (14) | 0.0122 (8) | −0.0086 (10) | −0.0078 (9) |
O2 | 0.0564 (12) | 0.0333 (10) | 0.0683 (14) | 0.0136 (9) | −0.0030 (10) | −0.0075 (9) |
O3 | 0.0472 (12) | 0.0354 (10) | 0.0866 (16) | 0.0150 (9) | −0.0015 (10) | 0.0072 (10) |
O4 | 0.0541 (12) | 0.0429 (11) | 0.0983 (18) | 0.0231 (10) | −0.0060 (11) | 0.0102 (11) |
C1 | 0.0487 (16) | 0.0417 (15) | 0.0372 (15) | 0.0172 (12) | 0.0131 (13) | 0.0067 (12) |
C2 | 0.0610 (19) | 0.0568 (18) | 0.0498 (18) | 0.0287 (15) | 0.0057 (15) | 0.0108 (15) |
C3 | 0.0520 (18) | 0.067 (2) | 0.057 (2) | 0.0164 (16) | −0.0088 (15) | 0.0026 (16) |
C4 | 0.0527 (17) | 0.0449 (16) | 0.0514 (18) | 0.0078 (14) | 0.0032 (14) | −0.0004 (14) |
C5 | 0.0448 (15) | 0.0379 (14) | 0.0393 (15) | 0.0146 (12) | 0.0093 (12) | 0.0013 (12) |
C6 | 0.0376 (14) | 0.0392 (14) | 0.0376 (15) | 0.0112 (11) | 0.0088 (12) | 0.0000 (12) |
C7 | 0.088 (2) | 0.0387 (17) | 0.090 (3) | 0.0218 (16) | −0.012 (2) | −0.0151 (17) |
C8 | 0.0631 (18) | 0.0391 (15) | 0.0496 (18) | 0.0172 (13) | 0.0180 (15) | 0.0069 (13) |
C9 | 0.0455 (16) | 0.0478 (16) | 0.0486 (18) | 0.0156 (13) | 0.0073 (13) | −0.0007 (13) |
C10 | 0.0522 (17) | 0.0555 (17) | 0.0513 (18) | 0.0239 (14) | 0.0057 (14) | −0.0002 (14) |
C11 | 0.0528 (16) | 0.0407 (15) | 0.0444 (17) | 0.0182 (13) | 0.0010 (13) | 0.0017 (12) |
C12 | 0.071 (2) | 0.0406 (15) | 0.0440 (17) | 0.0203 (14) | 0.0123 (15) | 0.0062 (13) |
C13 | 0.0564 (18) | 0.0440 (16) | 0.0353 (15) | 0.0168 (13) | 0.0121 (13) | 0.0024 (12) |
C14 | 0.0430 (16) | 0.0423 (15) | 0.0414 (16) | 0.0148 (13) | 0.0028 (12) | −0.0019 (12) |
C15 | 0.0513 (17) | 0.0476 (17) | 0.0441 (17) | 0.0231 (14) | 0.0032 (13) | 0.0005 (13) |
C16 | 0.0501 (18) | 0.070 (2) | 0.060 (2) | 0.0296 (16) | 0.0081 (15) | 0.0043 (16) |
C17 | 0.0461 (17) | 0.080 (2) | 0.072 (2) | 0.0178 (17) | 0.0189 (16) | 0.0053 (19) |
C18 | 0.059 (2) | 0.0531 (18) | 0.059 (2) | 0.0083 (15) | 0.0222 (16) | 0.0042 (15) |
C19 | 0.078 (2) | 0.058 (2) | 0.093 (3) | 0.0403 (18) | −0.001 (2) | 0.0129 (19) |
Geometric parameters (Å, º) top
N1—C9 | 1.452 (3) | C7—H7C | 0.9600 |
N1—C8 | 1.466 (3) | C8—H8A | 0.9700 |
N1—H1 | 0.9000 | C8—H8B | 0.9700 |
N2—C11 | 1.459 (3) | C9—C10 | 1.504 (4) |
N2—C12 | 1.471 (3) | C9—H9A | 0.9700 |
N2—H2 | 0.9000 | C9—H9B | 0.9700 |
O1—C6 | 1.352 (3) | C10—C11 | 1.503 (4) |
O1—H1A | 0.8200 | C10—H10A | 0.9700 |
O2—C5 | 1.371 (3) | C10—H10B | 0.9700 |
O2—C7 | 1.417 (3) | C11—H11A | 0.9700 |
O3—C14 | 1.354 (3) | C11—H11B | 0.9700 |
O3—H3 | 0.8200 | C12—C13 | 1.514 (4) |
O4—C15 | 1.364 (3) | C12—H12A | 0.9700 |
O4—C19 | 1.420 (3) | C12—H12B | 0.9700 |
C1—C2 | 1.385 (4) | C13—C14 | 1.384 (4) |
C1—C6 | 1.394 (3) | C13—C18 | 1.386 (4) |
C1—C8 | 1.507 (4) | C14—C15 | 1.397 (3) |
C2—C3 | 1.369 (4) | C15—C16 | 1.376 (4) |
C2—H2A | 0.9300 | C16—C17 | 1.376 (4) |
C3—C4 | 1.380 (4) | C16—H16 | 0.9300 |
C3—H3A | 0.9300 | C17—C18 | 1.369 (4) |
C4—C5 | 1.370 (4) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.401 (3) | C19—H19A | 0.9600 |
C7—H7A | 0.9600 | C19—H19B | 0.9600 |
C7—H7B | 0.9600 | C19—H19C | 0.9600 |
| | | |
C9—N1—C8 | 115.4 (2) | C10—C9—H9B | 109.5 |
C9—N1—H1 | 107.9 | H9A—C9—H9B | 108.1 |
C8—N1—H1 | 108.0 | C11—C10—C9 | 114.1 (2) |
C11—N2—C12 | 113.8 (2) | C11—C10—H10A | 108.7 |
C11—N2—H2 | 108.4 | C9—C10—H10A | 108.7 |
C12—N2—H2 | 108.3 | C11—C10—H10B | 108.7 |
C6—O1—H1A | 109.5 | C9—C10—H10B | 108.7 |
C5—O2—C7 | 117.9 (2) | H10A—C10—H10B | 107.6 |
C14—O3—H3 | 109.5 | N2—C11—C10 | 111.3 (2) |
C15—O4—C19 | 119.4 (2) | N2—C11—H11A | 109.4 |
C2—C1—C6 | 118.8 (2) | C10—C11—H11A | 109.4 |
C2—C1—C8 | 121.2 (2) | N2—C11—H11B | 109.4 |
C6—C1—C8 | 119.9 (2) | C10—C11—H11B | 109.4 |
C3—C2—C1 | 121.1 (3) | H11A—C11—H11B | 108.0 |
C3—C2—H2A | 119.4 | N2—C12—C13 | 115.3 (2) |
C1—C2—H2A | 119.4 | N2—C12—H12A | 108.5 |
C2—C3—C4 | 120.4 (3) | C13—C12—H12A | 108.5 |
C2—C3—H3A | 119.8 | N2—C12—H12B | 108.5 |
C4—C3—H3A | 119.8 | C13—C12—H12B | 108.5 |
C5—C4—C3 | 119.7 (3) | H12A—C12—H12B | 107.5 |
C5—C4—H4 | 120.1 | C14—C13—C18 | 118.6 (3) |
C3—C4—H4 | 120.1 | C14—C13—C12 | 120.2 (2) |
C4—C5—O2 | 125.3 (2) | C18—C13—C12 | 121.2 (3) |
C4—C5—C6 | 120.4 (2) | O3—C14—C13 | 118.1 (2) |
O2—C5—C6 | 114.3 (2) | O3—C14—C15 | 121.9 (2) |
O1—C6—C1 | 119.1 (2) | C13—C14—C15 | 119.9 (2) |
O1—C6—C5 | 121.4 (2) | O4—C15—C16 | 125.1 (2) |
C1—C6—C5 | 119.5 (2) | O4—C15—C14 | 114.6 (2) |
O2—C7—H7A | 109.5 | C16—C15—C14 | 120.3 (3) |
O2—C7—H7B | 109.5 | C15—C16—C17 | 119.5 (3) |
H7A—C7—H7B | 109.5 | C15—C16—H16 | 120.3 |
O2—C7—H7C | 109.5 | C17—C16—H16 | 120.3 |
H7A—C7—H7C | 109.5 | C18—C17—C16 | 120.4 (3) |
H7B—C7—H7C | 109.5 | C18—C17—H17 | 119.8 |
N1—C8—C1 | 117.4 (2) | C16—C17—H17 | 119.8 |
N1—C8—H8A | 107.9 | C17—C18—C13 | 121.2 (3) |
C1—C8—H8A | 107.9 | C17—C18—H18 | 119.4 |
N1—C8—H8B | 107.9 | C13—C18—H18 | 119.4 |
C1—C8—H8B | 107.9 | O4—C19—H19A | 109.5 |
H8A—C8—H8B | 107.2 | O4—C19—H19B | 109.5 |
N1—C9—C10 | 110.9 (2) | H19A—C19—H19B | 109.5 |
N1—C9—H9A | 109.5 | O4—C19—H19C | 109.5 |
C10—C9—H9A | 109.5 | H19A—C19—H19C | 109.5 |
N1—C9—H9B | 109.5 | H19B—C19—H19C | 109.5 |
| | | |
C6—C1—C2—C3 | 1.0 (4) | C12—N2—C11—C10 | −177.7 (2) |
C8—C1—C2—C3 | −174.7 (3) | C9—C10—C11—N2 | 178.5 (2) |
C1—C2—C3—C4 | 0.9 (5) | C11—N2—C12—C13 | 55.8 (3) |
C2—C3—C4—C5 | −1.4 (5) | N2—C12—C13—C14 | 55.3 (3) |
C3—C4—C5—O2 | 179.4 (3) | N2—C12—C13—C18 | −125.7 (3) |
C3—C4—C5—C6 | 0.1 (4) | C18—C13—C14—O3 | −179.6 (3) |
C7—O2—C5—C4 | −3.4 (4) | C12—C13—C14—O3 | −0.5 (4) |
C7—O2—C5—C6 | 175.9 (3) | C18—C13—C14—C15 | 0.5 (4) |
C2—C1—C6—O1 | 179.0 (2) | C12—C13—C14—C15 | 179.6 (2) |
C8—C1—C6—O1 | −5.3 (4) | C19—O4—C15—C16 | −1.3 (4) |
C2—C1—C6—C5 | −2.3 (4) | C19—O4—C15—C14 | 178.1 (3) |
C8—C1—C6—C5 | 173.4 (2) | O3—C14—C15—O4 | 0.8 (4) |
C4—C5—C6—O1 | −179.5 (3) | C13—C14—C15—O4 | −179.3 (2) |
O2—C5—C6—O1 | 1.1 (4) | O3—C14—C15—C16 | −179.8 (3) |
C4—C5—C6—C1 | 1.8 (4) | C13—C14—C15—C16 | 0.1 (4) |
O2—C5—C6—C1 | −177.6 (2) | O4—C15—C16—C17 | 178.7 (3) |
C9—N1—C8—C1 | 62.0 (3) | C14—C15—C16—C17 | −0.6 (4) |
C2—C1—C8—N1 | −125.2 (3) | C15—C16—C17—C18 | 0.4 (5) |
C6—C1—C8—N1 | 59.2 (3) | C16—C17—C18—C13 | 0.3 (5) |
C8—N1—C9—C10 | −174.0 (2) | C14—C13—C18—C17 | −0.7 (4) |
N1—C9—C10—C11 | −174.2 (2) | C12—C13—C18—C17 | −179.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.90 | 2.45 | 2.895 (3) | 111 |
O3—H3···N1i | 0.82 | 1.90 | 2.674 (3) | 157 |
N2—H2···O1ii | 0.90 | 1.83 | 2.721 (3) | 170 |
N2—H2···O2ii | 0.90 | 2.65 | 2.951 (3) | 101 |
C7—H7B···O3ii | 0.96 | 2.69 | 3.536 (4) | 148 |
C19—H19B···O1i | 0.96 | 2.69 | 3.491 (4) | 141 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1. |