Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016269/cf6103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016269/cf6103Isup2.hkl |
CCDC reference: 176004
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.004 Å
- R factor = 0.063
- wR factor = 0.106
- Data-to-parameter ratio = 9.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.154 Weighting scheme identified as calc General Notes
GOODF_01 _refine_ls_goodness_of_fit_obs is an old dataname which has been superseded by _refine_ls_goodness_of_fit_ref REFLE_01 _reflns_observed_criterion is an old dataname which has been superseded by _reflns_threshold_expression REFLG_01 _reflns_number_observed is an old dataname which has been superseded by _reflns_number_gt RFACG_01 _refine_ls_R_factor_obs is an old dataname which has been superseded by _refine_ls_R_factor_gt RFACR_01 _refine_ls_wR_factor_obs is an old dataname which has been superseded by _refine_ls_wR_factor_ref SHFSU_01 _refine_ls_shift/esd_max is an old dataname which has been superseded by _refine_ls_shift/su_max
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson 1976); software used to prepare material for publication: SHELXL93.
C18H20N2O2 | F(000) = 316 |
Mr = 296.36 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7330 (2) Å | Cell parameters from 22914 reflections |
b = 5.8710 (3) Å | θ = 0.3–25.0° |
c = 15.3070 (6) Å | µ = 0.08 mm−1 |
β = 90.535 (1)° | T = 123 K |
V = 784.78 (5) Å3 | Fragment, yellow |
Z = 2 | 0.40 × 0.30 × 0.15 mm |
Nonius KappaCCD diffractometer | 910 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 24.9°, θmin = 3.7° |
ϕ and ω scans | h = 0→10 |
2537 measured reflections | k = −6→6 |
1358 independent reflections | l = −17→18 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | All H-atom parameters refined |
S = 1.19 | Calculated w = 1/[σ2(Fo2) + (0.0434P)2 + 0.1547P] where P = (Fo2 + 2Fc2)/3 |
1349 reflections | (Δ/σ)max < 0.001 |
140 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C18H20N2O2 | V = 784.78 (5) Å3 |
Mr = 296.36 | Z = 2 |
Monoclinic, P21/a | Mo Kα radiation |
a = 8.7330 (2) Å | µ = 0.08 mm−1 |
b = 5.8710 (3) Å | T = 123 K |
c = 15.3070 (6) Å | 0.40 × 0.30 × 0.15 mm |
β = 90.535 (1)° |
Nonius KappaCCD diffractometer | 910 reflections with I > 2σ(I) |
2537 measured reflections | Rint = 0.069 |
1358 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.135 | All H-atom parameters refined |
S = 1.19 | Δρmax = 0.17 e Å−3 |
1349 reflections | Δρmin = −0.17 e Å−3 |
140 parameters |
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 on F2 for ALL reflections except for 9 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1790 (2) | 0.7137 (3) | 0.32013 (12) | 0.0290 (5) | |
N1 | 0.0452 (2) | 0.3245 (4) | 0.34121 (14) | 0.0244 (6) | |
C9 | 0.0451 (3) | 0.0878 (5) | 0.4742 (2) | 0.0248 (7) | |
C8 | −0.0418 (3) | 0.1595 (5) | 0.3919 (2) | 0.0270 (7) | |
C7 | 0.0870 (3) | 0.2682 (5) | 0.2638 (2) | 0.0232 (7) | |
C6 | 0.1796 (3) | 0.4203 (5) | 0.2104 (2) | 0.0209 (7) | |
C5 | 0.2285 (3) | 0.3505 (5) | 0.1278 (2) | 0.0248 (7) | |
C4 | 0.3224 (3) | 0.4866 (5) | 0.0780 (2) | 0.0284 (7) | |
C3 | 0.3686 (3) | 0.6968 (5) | 0.1103 (2) | 0.0281 (7) | |
C2 | 0.3201 (3) | 0.7715 (5) | 0.1909 (2) | 0.0260 (7) | |
C1 | 0.2250 (3) | 0.6354 (5) | 0.2414 (2) | 0.0233 (7) | |
H5 | 0.193 (3) | 0.199 (5) | 0.1071 (16) | 0.027 (7)* | |
H6 | 0.059 (3) | 0.116 (5) | 0.2399 (16) | 0.028 (7)* | |
H8 | −0.068 (3) | 0.020 (5) | 0.3579 (17) | 0.030 (7)* | |
H2 | 0.352 (2) | 0.918 (5) | 0.2138 (15) | 0.020 (7)* | |
H7 | −0.144 (3) | 0.238 (5) | 0.4099 (17) | 0.038 (8)* | |
H9 | 0.146 (3) | 0.016 (4) | 0.4559 (15) | 0.018 (6)* | |
H3 | 0.436 (3) | 0.797 (5) | 0.0770 (17) | 0.033 (8)* | |
H4 | 0.351 (3) | 0.433 (5) | 0.0200 (18) | 0.032 (7)* | |
H10 | 0.069 (3) | 0.233 (5) | 0.5100 (19) | 0.044 (9)* | |
H1 | 0.119 (4) | 0.583 (7) | 0.348 (3) | 0.094 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0353 (11) | 0.0290 (12) | 0.0227 (12) | 0.0018 (9) | 0.0022 (9) | −0.0056 (10) |
N1 | 0.0220 (12) | 0.0303 (15) | 0.0208 (14) | 0.0003 (10) | 0.0003 (10) | 0.0029 (12) |
C9 | 0.023 (2) | 0.030 (2) | 0.022 (2) | −0.0018 (13) | 0.0002 (12) | 0.0027 (14) |
C8 | 0.024 (2) | 0.032 (2) | 0.025 (2) | −0.0052 (14) | −0.0016 (13) | 0.0043 (15) |
C7 | 0.0210 (14) | 0.026 (2) | 0.022 (2) | 0.0013 (13) | −0.0044 (12) | 0.0016 (14) |
C6 | 0.0207 (14) | 0.024 (2) | 0.018 (2) | 0.0019 (12) | −0.0022 (12) | 0.0022 (13) |
C5 | 0.031 (2) | 0.024 (2) | 0.019 (2) | 0.0013 (13) | −0.0037 (13) | 0.0013 (14) |
C4 | 0.033 (2) | 0.034 (2) | 0.018 (2) | 0.0006 (14) | 0.0028 (13) | 0.0001 (15) |
C3 | 0.027 (2) | 0.031 (2) | 0.026 (2) | −0.0003 (14) | 0.0045 (13) | 0.0113 (15) |
C2 | 0.027 (2) | 0.023 (2) | 0.028 (2) | −0.0004 (13) | −0.0032 (13) | 0.000 (2) |
C1 | 0.0220 (14) | 0.026 (2) | 0.022 (2) | 0.0044 (13) | −0.0039 (12) | 0.0031 (14) |
O1—C1 | 1.354 (3) | C7—H6 | 1.00 (3) |
O1—H1 | 1.03 (4) | C6—C5 | 1.399 (3) |
N1—C7 | 1.286 (3) | C6—C1 | 1.405 (4) |
N1—C8 | 1.460 (3) | C5—C4 | 1.380 (4) |
C9—C9i | 1.522 (5) | C5—H5 | 0.99 (3) |
C9—C8 | 1.524 (4) | C4—C3 | 1.388 (4) |
C9—H9 | 1.02 (2) | C4—H4 | 0.98 (3) |
C9—H10 | 1.03 (3) | C3—C2 | 1.380 (4) |
C8—H8 | 1.00 (3) | C3—H3 | 0.98 (3) |
C8—H7 | 1.05 (3) | C2—C1 | 1.392 (4) |
C7—C6 | 1.460 (4) | C2—H2 | 0.97 (3) |
C1—O1—H1 | 106 (2) | C5—C6—C7 | 120.1 (3) |
C7—N1—C8 | 118.2 (2) | C1—C6—C7 | 121.1 (2) |
C9i—C9—C8 | 111.1 (3) | C4—C5—C6 | 121.2 (3) |
C9i—C9—H9 | 108.4 (13) | C4—C5—H5 | 121.7 (14) |
C8—C9—H9 | 108.2 (13) | C6—C5—H5 | 117.1 (14) |
C9i—C9—H10 | 112.7 (15) | C5—C4—C3 | 119.3 (3) |
C8—C9—H10 | 107.7 (16) | C5—C4—H4 | 118.5 (16) |
H9—C9—H10 | 108.5 (19) | C3—C4—H4 | 122.1 (16) |
N1—C8—C9 | 111.4 (2) | C2—C3—C4 | 120.7 (3) |
N1—C8—H8 | 112.7 (15) | C2—C3—H3 | 117.9 (16) |
C9—C8—H8 | 108.5 (15) | C4—C3—H3 | 121.5 (16) |
N1—C8—H7 | 107.4 (15) | C3—C2—C1 | 120.3 (3) |
C9—C8—H7 | 109.0 (15) | C3—C2—H2 | 121.0 (13) |
H8—C8—H7 | 108 (2) | C1—C2—H2 | 118.8 (14) |
N1—C7—C6 | 121.4 (3) | O1—C1—C2 | 118.9 (3) |
N1—C7—H6 | 119.8 (14) | O1—C1—C6 | 121.4 (2) |
C6—C7—H6 | 118.7 (14) | C2—C1—C6 | 119.7 (3) |
C5—C6—C1 | 118.7 (3) |
Symmetry code: (i) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H20N2O2 |
Mr | 296.36 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 123 |
a, b, c (Å) | 8.7330 (2), 5.8710 (3), 15.3070 (6) |
β (°) | 90.535 (1) |
V (Å3) | 784.78 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.30 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2537, 1358, 910 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.592 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.135, 1.19 |
No. of reflections | 1349 |
No. of parameters | 140 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL93 (Sheldrick, 1993), ORTEPII (Johnson 1976), SHELXL93.
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During our studies on the synthesis and structure of simple Schiff base complexes of zinc, we retrieved from the mother liquors a crystalline sample of N,N'-bis(salicylidene)-1,4-butanediamine (Pfeiffer et al., 1937) (m. p. 362 K). Although this compound has been known for some time, its structure remains unreported. As a consequence of our current interest in Schiff base complexes with larger diimide backbones and the fact the analogous 1,2-ethylenediamine (Pahor et al., 1978) and 1,3-propylenediamine (Elderman et al., 1991) structures are known, we formed the opinion that it would be instructive to solve and report the structure of this higher homologue.