Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027754/at2308sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027754/at2308Isup2.hkl |
CCDC reference: 649511
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.144
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. N1 .. 2.80 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C4 .. N1 .. 97.90 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Solutions of hypnone (20 mmol) and benzene-1,2-diamie (10 mmol) in benzene (30 ml) was stirred for 6 h and then mixtures was filtered, and then solution was left to produce crystals of (I) slowly.
All H atoms were located in difference Fourier maps. H atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), and Uiso(H) = 1.2Ueq(C) for aryl or 1.5 Ueq(C) for methyl.
As part of our investigation of the reactions between hypnone with diamines, we report here the crystal structure of a hypnone Schiff base, N,N'-bis(3-methoxy-2-hydroxybenzylidene) benzene-1, 4-diamie, (I) and (Fig. 1).
The asymmetric unit consists of one half-molecule. The molecule have an inversion centre at the mid-point of the central benzen ring. The dihedral angle between the neighbouring benzen rings in the molecule is 74.10 (10) °. The bond lengths and angles are normal (Allen et al., 1987) and are in agreement with those in two similar compounds (Xia et al.., 2007; Liu et al., 2006). The molecules are linked into a chain of ring by C—H···N hydrogen bonds. Atom C11 in the molecule (x, y, z) act as hydrogen-bond donor to atom N1 in the molecule (- x, - y, 1 - z), generating a chain of R22(8) rings (Bernstein et al., 1995) along the b-axisdirection (Fig. 2 and Table 1). Neighbouring chains are linked by C—H···π hydrogen bonds into the sheets (Fig. 3) and there are no direction-specific interactions between adjacent sheets.
For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Hodnett & Dunn (1970); Liu et al. (2006); Modi et al. (1970); Xia et al. (2007).
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.
C22H20N2 | F(000) = 332 |
Mr = 312.40 | Dx = 1.165 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 770 reflections |
a = 5.9718 (11) Å | θ = 3.1–23.0° |
b = 6.8701 (15) Å | µ = 0.07 mm−1 |
c = 21.713 (2) Å | T = 298 K |
β = 90.720 (2)° | Block, colourless |
V = 890.8 (3) Å3 | 0.45 × 0.42 × 0.19 mm |
Z = 2 |
Siemens SMART 1000 CCD area-detector diffractometer | 1560 independent reflections |
Radiation source: fine-focus sealed tube | 879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→6 |
Tmin = 0.970, Tmax = 0.987 | k = −7→8 |
3502 measured reflections | l = −25→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.0928P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
1560 reflections | Δρmax = 0.21 e Å−3 |
110 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.035 (5) |
C22H20N2 | V = 890.8 (3) Å3 |
Mr = 312.40 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.9718 (11) Å | µ = 0.07 mm−1 |
b = 6.8701 (15) Å | T = 298 K |
c = 21.713 (2) Å | 0.45 × 0.42 × 0.19 mm |
β = 90.720 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 1560 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 879 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.987 | Rint = 0.046 |
3502 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
1560 reflections | Δρmin = −0.15 e Å−3 |
110 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 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1054 (3) | 0.1888 (3) | 0.42130 (8) | 0.0520 (6) | |
C1 | 0.5090 (4) | 0.2304 (5) | 0.43650 (14) | 0.0942 (11) | |
H1A | 0.4661 | 0.3410 | 0.4606 | 0.141* | |
H1B | 0.6053 | 0.2719 | 0.4039 | 0.141* | |
H1C | 0.5871 | 0.1386 | 0.4623 | 0.141* | |
C2 | 0.3038 (4) | 0.1361 (3) | 0.40941 (10) | 0.0466 (6) | |
C3 | 0.3318 (4) | −0.0279 (3) | 0.36540 (10) | 0.0467 (6) | |
C4 | 0.1630 (4) | −0.0695 (4) | 0.32348 (11) | 0.0582 (7) | |
H4 | 0.0326 | 0.0045 | 0.3234 | 0.070* | |
C5 | 0.1853 (5) | −0.2190 (5) | 0.28178 (12) | 0.0774 (9) | |
H5 | 0.0716 | −0.2433 | 0.2531 | 0.093* | |
C6 | 0.3754 (6) | −0.3328 (5) | 0.28231 (14) | 0.0844 (10) | |
H6 | 0.3896 | −0.4346 | 0.2544 | 0.101* | |
C7 | 0.5421 (6) | −0.2951 (5) | 0.32399 (15) | 0.0838 (10) | |
H7 | 0.6700 | −0.3723 | 0.3249 | 0.101* | |
C8 | 0.5219 (4) | −0.1423 (4) | 0.36498 (12) | 0.0671 (8) | |
H8 | 0.6380 | −0.1161 | 0.3927 | 0.080* | |
C9 | 0.0613 (3) | 0.3471 (3) | 0.46147 (10) | 0.0448 (6) | |
C10 | 0.0549 (4) | 0.5353 (4) | 0.43993 (11) | 0.0532 (7) | |
H10 | 0.0903 | 0.5604 | 0.3991 | 0.064* | |
C11 | 0.0035 (4) | 0.3121 (4) | 0.52201 (10) | 0.0523 (7) | |
H11 | 0.0039 | 0.1855 | 0.5371 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0428 (12) | 0.0496 (14) | 0.0636 (13) | −0.0032 (10) | 0.0030 (10) | −0.0110 (10) |
C1 | 0.0482 (17) | 0.105 (3) | 0.129 (3) | −0.0022 (18) | −0.0095 (17) | −0.047 (2) |
C2 | 0.0404 (14) | 0.0492 (16) | 0.0502 (13) | −0.0039 (12) | 0.0011 (10) | −0.0013 (11) |
C3 | 0.0453 (15) | 0.0469 (16) | 0.0481 (13) | 0.0004 (12) | 0.0090 (11) | 0.0030 (11) |
C4 | 0.0625 (17) | 0.0571 (18) | 0.0550 (15) | −0.0008 (14) | 0.0014 (12) | −0.0043 (13) |
C5 | 0.092 (2) | 0.076 (2) | 0.0647 (18) | −0.0074 (19) | 0.0038 (15) | −0.0183 (16) |
C6 | 0.105 (3) | 0.074 (2) | 0.075 (2) | −0.001 (2) | 0.0305 (19) | −0.0197 (17) |
C7 | 0.084 (2) | 0.075 (2) | 0.093 (2) | 0.0217 (19) | 0.0296 (19) | −0.0062 (19) |
C8 | 0.0564 (17) | 0.073 (2) | 0.0722 (18) | 0.0092 (16) | 0.0067 (13) | −0.0050 (15) |
C9 | 0.0363 (13) | 0.0415 (15) | 0.0566 (14) | −0.0056 (11) | −0.0001 (10) | −0.0094 (12) |
C10 | 0.0581 (16) | 0.0508 (17) | 0.0510 (14) | −0.0081 (13) | 0.0068 (12) | −0.0020 (13) |
C11 | 0.0541 (15) | 0.0444 (15) | 0.0586 (16) | −0.0040 (13) | 0.0012 (11) | 0.0009 (12) |
N1—C2 | 1.268 (3) | C5—H5 | 0.9300 |
N1—C9 | 1.421 (3) | C6—C7 | 1.362 (4) |
C1—C2 | 1.500 (3) | C6—H6 | 0.9300 |
C1—H1A | 0.9600 | C7—C8 | 1.382 (4) |
C1—H1B | 0.9600 | C7—H7 | 0.9300 |
C1—H1C | 0.9600 | C8—H8 | 0.9300 |
C2—C3 | 1.489 (3) | C9—C10 | 1.376 (3) |
C3—C4 | 1.379 (3) | C9—C11 | 1.384 (3) |
C3—C8 | 1.381 (3) | C10—C11i | 1.382 (3) |
C4—C5 | 1.377 (3) | C10—H10 | 0.9300 |
C4—H4 | 0.9300 | C11—C10i | 1.382 (3) |
C5—C6 | 1.378 (4) | C11—H11 | 0.9300 |
C2—N1—C9 | 121.6 (2) | C7—C6—C5 | 119.5 (3) |
C2—C1—H1A | 109.5 | C7—C6—H6 | 120.2 |
C2—C1—H1B | 109.5 | C5—C6—H6 | 120.2 |
H1A—C1—H1B | 109.5 | C6—C7—C8 | 120.2 (3) |
C2—C1—H1C | 109.5 | C6—C7—H7 | 119.9 |
H1A—C1—H1C | 109.5 | C8—C7—H7 | 119.9 |
H1B—C1—H1C | 109.5 | C3—C8—C7 | 121.0 (3) |
N1—C2—C3 | 117.3 (2) | C3—C8—H8 | 119.5 |
N1—C2—C1 | 123.9 (2) | C7—C8—H8 | 119.5 |
C3—C2—C1 | 118.7 (2) | C10—C9—C11 | 118.7 (2) |
C4—C3—C8 | 118.2 (2) | C10—C9—N1 | 121.0 (2) |
C4—C3—C2 | 119.6 (2) | C11—C9—N1 | 120.0 (2) |
C8—C3—C2 | 122.3 (2) | C9—C10—C11i | 121.0 (2) |
C5—C4—C3 | 120.8 (3) | C9—C10—H10 | 119.5 |
C5—C4—H4 | 119.6 | C11i—C10—H10 | 119.5 |
C3—C4—H4 | 119.6 | C10i—C11—C9 | 120.3 (2) |
C4—C5—C6 | 120.3 (3) | C10i—C11—H11 | 119.9 |
C4—C5—H5 | 119.9 | C9—C11—H11 | 119.9 |
C6—C5—H5 | 119.9 | ||
C9—N1—C2—C3 | −178.4 (2) | C5—C6—C7—C8 | −0.7 (5) |
C9—N1—C2—C1 | 1.0 (4) | C4—C3—C8—C7 | −0.4 (4) |
N1—C2—C3—C4 | 23.3 (3) | C2—C3—C8—C7 | 179.3 (2) |
C1—C2—C3—C4 | −156.2 (2) | C6—C7—C8—C3 | 1.3 (4) |
N1—C2—C3—C8 | −156.4 (2) | C2—N1—C9—C10 | 86.1 (3) |
C1—C2—C3—C8 | 24.1 (3) | C2—N1—C9—C11 | −99.9 (3) |
C8—C3—C4—C5 | −1.0 (4) | C11—C9—C10—C11i | 1.3 (4) |
C2—C3—C4—C5 | 179.3 (2) | N1—C9—C10—C11i | 175.4 (2) |
C3—C4—C5—C6 | 1.5 (4) | C10—C9—C11—C10i | −1.3 (4) |
C4—C5—C6—C7 | −0.7 (4) | N1—C9—C11—C10i | −175.4 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N1 | 0.93 | 2.51 | 2.792 (3) | 98 |
C11—H11···N1ii | 0.93 | 2.80 | 3.715 (3) | 166 |
Symmetry code: (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H20N2 |
Mr | 312.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 5.9718 (11), 6.8701 (15), 21.713 (2) |
β (°) | 90.720 (2) |
V (Å3) | 890.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.45 × 0.42 × 0.19 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.970, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3502, 1560, 879 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.144, 1.02 |
No. of reflections | 1560 |
No. of parameters | 110 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.15 |
Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N1 | 0.93 | 2.51 | 2.792 (3) | 97.9 |
C11—H11···N1i | 0.93 | 2.80 | 3.715 (3) | 166.4 |
Symmetry code: (i) −x, −y, −z+1. |
As part of our investigation of the reactions between hypnone with diamines, we report here the crystal structure of a hypnone Schiff base, N,N'-bis(3-methoxy-2-hydroxybenzylidene) benzene-1, 4-diamie, (I) and (Fig. 1).
The asymmetric unit consists of one half-molecule. The molecule have an inversion centre at the mid-point of the central benzen ring. The dihedral angle between the neighbouring benzen rings in the molecule is 74.10 (10) °. The bond lengths and angles are normal (Allen et al., 1987) and are in agreement with those in two similar compounds (Xia et al.., 2007; Liu et al., 2006). The molecules are linked into a chain of ring by C—H···N hydrogen bonds. Atom C11 in the molecule (x, y, z) act as hydrogen-bond donor to atom N1 in the molecule (- x, - y, 1 - z), generating a chain of R22(8) rings (Bernstein et al., 1995) along the b-axisdirection (Fig. 2 and Table 1). Neighbouring chains are linked by C—H···π hydrogen bonds into the sheets (Fig. 3) and there are no direction-specific interactions between adjacent sheets.