Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027420/is2174sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027420/is2174Isup2.hkl |
CCDC reference: 654976
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.053
- wR factor = 0.154
- Data-to-parameter ratio = 29.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 30 Ang. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.95 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check
For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Eltayeb, Teoh, Chantrapromma et al. (2007); Eltayeb, Teoh, Teh et al. (2007a,b). For related literature on pharmacological activities and applications, see, for example: Dao et al. (2000); Karthikeyan et al. (2006); Sriram et al. (2006); Eltayeb & Ahmed (2005a,b).
The title compound was synthesized by adding 5-methoxysalicylaldehyde (0.4 ml, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Red plate-shaped single crystals of (I) suitable for X-ray structure determination were formed after two days of slow evaporation of the solvent at room temperature.
All H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H distances of 0.86–0.90 Å and C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.
Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). We have previously reported the crystal structures of Schiff base ligands which are 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a), 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b) and 5,5'-dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007). As an extension of our investigations of Schiff base ligands and complexes, the title compound, (I), was synthesized by the reaction of o-phenylenediamine with 5-methoxysalicylaldehyde, and its crystal structure is reported here.
The structure of the title compound is not planar. The orientations of the C1–C6 and C15–C20 benzene rings respect to the o-phenylenediamine unit are indicated by the dihedral angles of 36.35 (5) and 17.81 (5)°, respectively. The C1–C6 and C15–C20 benzene rings makes the dihedral angle of 43.94 (5)°. The two methoxy groups are planarly attached to the C1–C6 and C15–C20 benzene rings. The C8/N1/C7/C6 unit is not planar as indicated by the torsion angles C8/N1/C7/C6 = -171.09 (8)° while the C13/N2/C14/C15 unit is planarly attached with the torsion angle of 178.91 (8)°. The orientations of these units with respect to the o-phenylenediamine ring are shown by the torsion angles C7/N1/C8/C9 = 31.92 (13)° and C14/N2/C13/C12 = -22.97 (14)°.
The two intramolecular hydrogen bonds, O1—H1O1···N1 and O3—H1O3···N2 generate S(6) ring motifs (Bernstein et al., 1995). Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb et al., 2007; Eltayeb et al., 2007a,b).
In the crystal, the molecules are arranged into chains along the c axis. These chains form molecular sheets parallel to the ac plane (Fig. 2). The crystal is stabilized by O—H···N intramolecular hydrogen bonds (Table 1) and further stabilized by C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C8–C13 and C15–C20 benzene rings, respectively.
For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see, for example: Eltayeb, Teoh, Chantrapromma et al. (2007); Eltayeb, Teoh, Teh et al. (2007a,b). For related literature on pharmacological activities and applications, see, for example: Dao et al. (2000); Karthikeyan et al. (2006); Sriram et al. (2006); Eltayeb & Ahmed (2005a,b).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C22H20N2O4 | F(000) = 792 |
Mr = 376.40 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8095 reflections |
a = 11.6772 (3) Å | θ = 2.3–35.0° |
b = 13.8721 (3) Å | µ = 0.09 mm−1 |
c = 13.1182 (3) Å | T = 100 K |
β = 119.875 (2)° | Plate, red |
V = 1842.60 (8) Å3 | 0.57 × 0.47 × 0.12 mm |
Z = 4 |
Bruker SMART APEX II CCD area-detector diffractometer | 8095 independent reflections |
Radiation source: fine-focus sealed tube | 6228 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.0°, θmin = 2.3° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −22→22 |
Tmin = 0.948, Tmax = 0.989 | l = −21→21 |
36710 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0831P)2 + 0.3111P] where P = (Fo2 + 2Fc2)/3 |
8095 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C22H20N2O4 | V = 1842.60 (8) Å3 |
Mr = 376.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.6772 (3) Å | µ = 0.09 mm−1 |
b = 13.8721 (3) Å | T = 100 K |
c = 13.1182 (3) Å | 0.57 × 0.47 × 0.12 mm |
β = 119.875 (2)° |
Bruker SMART APEX II CCD area-detector diffractometer | 8095 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 6228 reflections with I > 2σ(I) |
Tmin = 0.948, Tmax = 0.989 | Rint = 0.049 |
36710 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.41 e Å−3 |
8095 reflections | Δρmin = −0.33 e Å−3 |
275 parameters |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | ||
O1 | 0.83325 (7) | 0.46826 (6) | 0.48148 (6) | 0.02043 (15) | |
H1O1 | 0.7502 | 0.4544 | 0.4461 | 0.062 (6)* | |
O2 | 1.06862 (7) | 0.28976 (6) | 0.91533 (7) | 0.02480 (16) | |
O3 | 0.72475 (7) | 0.41856 (6) | 0.21130 (6) | 0.02213 (15) | |
H1O3 | 0.6644 | 0.4180 | 0.2348 | 0.075 (7)* | |
O4 | 0.48112 (7) | 0.34127 (6) | −0.26517 (6) | 0.02223 (15) | |
N1 | 0.60911 (8) | 0.39635 (6) | 0.43686 (7) | 0.01623 (15) | |
N2 | 0.49232 (8) | 0.40442 (6) | 0.19622 (7) | 0.01599 (15) | |
C1 | 0.88570 (9) | 0.42265 (7) | 0.58656 (8) | 0.01575 (16) | |
C2 | 1.01832 (9) | 0.43830 (7) | 0.66858 (8) | 0.01768 (17) | |
H2A | 1.0690 | 0.4789 | 0.6503 | 0.024 (4)* | |
C3 | 1.07443 (9) | 0.39357 (7) | 0.77689 (8) | 0.01846 (17) | |
H3A | 1.1626 | 0.4052 | 0.8317 | 0.028 (4)* | |
C4 | 1.00057 (9) | 0.33070 (7) | 0.80566 (8) | 0.01765 (17) | |
C5 | 0.86873 (9) | 0.31521 (7) | 0.72544 (8) | 0.01713 (16) | |
H5A | 0.8192 | 0.2738 | 0.7441 | 0.025 (4)* | |
C6 | 0.80918 (9) | 0.36209 (7) | 0.61532 (8) | 0.01528 (16) | |
C7 | 0.66841 (9) | 0.35170 (7) | 0.53648 (8) | 0.01638 (16) | |
H7A | 0.6197 | 0.3121 | 0.5580 | 0.019 (3)* | |
C8 | 0.47016 (9) | 0.39602 (7) | 0.36932 (8) | 0.01505 (15) | |
C9 | 0.39089 (10) | 0.39297 (7) | 0.42200 (9) | 0.01845 (17) | |
H9A | 0.4305 | 0.3887 | 0.5033 | 0.032 (4)* | |
C10 | 0.25443 (10) | 0.39636 (8) | 0.35414 (9) | 0.02039 (18) | |
H10A | 0.2029 | 0.3916 | 0.3897 | 0.034 (4)* | |
C11 | 0.19468 (10) | 0.40685 (8) | 0.23291 (9) | 0.02124 (19) | |
H11A | 0.1032 | 0.4106 | 0.1876 | 0.029 (4)* | |
C12 | 0.27157 (9) | 0.41177 (8) | 0.17945 (9) | 0.01916 (18) | |
H12A | 0.2312 | 0.4200 | 0.0985 | 0.027 (4)* | |
C13 | 0.40965 (9) | 0.40438 (7) | 0.24637 (8) | 0.01541 (16) | |
C14 | 0.44488 (9) | 0.37959 (7) | 0.08798 (8) | 0.01615 (16) | |
H14A | 0.3568 | 0.3609 | 0.0448 | 0.028 (4)* | |
C15 | 0.52455 (9) | 0.37990 (7) | 0.03136 (8) | 0.01512 (15) | |
C16 | 0.46282 (9) | 0.35957 (7) | −0.08930 (8) | 0.01622 (16) | |
H16A | 0.3727 | 0.3469 | −0.1309 | 0.023 (3)* | |
C17 | 0.53497 (9) | 0.35827 (7) | −0.14717 (8) | 0.01730 (16) | |
C18 | 0.67094 (10) | 0.37513 (8) | −0.08346 (9) | 0.01983 (18) | |
H18A | 0.7201 | 0.3728 | −0.1215 | 0.038 (4)* | |
C19 | 0.73312 (10) | 0.39529 (7) | 0.03560 (9) | 0.01973 (18) | |
H19A | 0.8236 | 0.4066 | 0.0768 | 0.034 (4)* | |
C20 | 0.66080 (9) | 0.39875 (7) | 0.09450 (8) | 0.01706 (16) | |
C21 | 0.99719 (12) | 0.22443 (10) | 0.94684 (11) | 0.0321 (3) | |
H21A | 1.0553 | 0.1983 | 1.0234 | 0.047 (5)* | |
H21B | 0.9623 | 0.1731 | 0.8904 | 0.041 (5)* | |
H21C | 0.9259 | 0.2580 | 0.9480 | 0.038 (4)* | |
C22 | 0.34072 (10) | 0.33517 (8) | −0.33058 (9) | 0.02211 (19) | |
H22A | 0.3125 | 0.3243 | −0.4120 | 0.034 (4)* | |
H22B | 0.3033 | 0.3943 | −0.3226 | 0.038 (4)* | |
H22C | 0.3117 | 0.2827 | −0.3013 | 0.022 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0168 (3) | 0.0278 (4) | 0.0151 (3) | −0.0011 (3) | 0.0067 (2) | 0.0054 (3) |
O2 | 0.0181 (3) | 0.0329 (4) | 0.0166 (3) | −0.0015 (3) | 0.0035 (3) | 0.0090 (3) |
O3 | 0.0155 (3) | 0.0301 (4) | 0.0173 (3) | −0.0036 (3) | 0.0055 (3) | −0.0050 (3) |
O4 | 0.0211 (3) | 0.0304 (4) | 0.0165 (3) | 0.0008 (3) | 0.0104 (3) | −0.0006 (3) |
N1 | 0.0136 (3) | 0.0192 (3) | 0.0134 (3) | −0.0008 (3) | 0.0049 (3) | −0.0004 (3) |
N2 | 0.0141 (3) | 0.0180 (3) | 0.0152 (3) | 0.0007 (3) | 0.0068 (3) | 0.0005 (3) |
C1 | 0.0157 (4) | 0.0182 (4) | 0.0137 (3) | 0.0000 (3) | 0.0076 (3) | 0.0007 (3) |
C2 | 0.0146 (4) | 0.0206 (4) | 0.0178 (4) | −0.0021 (3) | 0.0081 (3) | 0.0003 (3) |
C3 | 0.0131 (4) | 0.0227 (4) | 0.0169 (4) | −0.0012 (3) | 0.0054 (3) | 0.0002 (3) |
C4 | 0.0158 (4) | 0.0210 (4) | 0.0137 (4) | 0.0002 (3) | 0.0054 (3) | 0.0021 (3) |
C5 | 0.0158 (4) | 0.0181 (4) | 0.0154 (4) | −0.0018 (3) | 0.0062 (3) | 0.0018 (3) |
C6 | 0.0134 (4) | 0.0165 (4) | 0.0139 (3) | −0.0014 (3) | 0.0052 (3) | −0.0002 (3) |
C7 | 0.0154 (4) | 0.0161 (4) | 0.0156 (4) | −0.0021 (3) | 0.0062 (3) | 0.0000 (3) |
C8 | 0.0131 (4) | 0.0156 (4) | 0.0149 (4) | −0.0001 (3) | 0.0058 (3) | 0.0003 (3) |
C9 | 0.0180 (4) | 0.0216 (4) | 0.0165 (4) | 0.0007 (3) | 0.0092 (3) | 0.0008 (3) |
C10 | 0.0173 (4) | 0.0242 (4) | 0.0219 (4) | 0.0017 (3) | 0.0114 (4) | 0.0008 (3) |
C11 | 0.0137 (4) | 0.0270 (5) | 0.0219 (4) | 0.0020 (3) | 0.0079 (3) | −0.0002 (3) |
C12 | 0.0142 (4) | 0.0250 (4) | 0.0158 (4) | 0.0022 (3) | 0.0055 (3) | 0.0001 (3) |
C13 | 0.0128 (4) | 0.0175 (4) | 0.0146 (4) | 0.0003 (3) | 0.0059 (3) | −0.0001 (3) |
C14 | 0.0139 (4) | 0.0184 (4) | 0.0150 (4) | 0.0003 (3) | 0.0064 (3) | 0.0005 (3) |
C15 | 0.0136 (4) | 0.0156 (4) | 0.0153 (4) | 0.0005 (3) | 0.0066 (3) | 0.0006 (3) |
C16 | 0.0139 (4) | 0.0182 (4) | 0.0158 (4) | 0.0006 (3) | 0.0068 (3) | 0.0008 (3) |
C17 | 0.0181 (4) | 0.0178 (4) | 0.0170 (4) | 0.0014 (3) | 0.0095 (3) | 0.0009 (3) |
C18 | 0.0177 (4) | 0.0210 (4) | 0.0232 (4) | 0.0010 (3) | 0.0120 (4) | 0.0002 (3) |
C19 | 0.0144 (4) | 0.0220 (4) | 0.0227 (4) | −0.0007 (3) | 0.0091 (3) | −0.0004 (3) |
C20 | 0.0147 (4) | 0.0169 (4) | 0.0173 (4) | 0.0003 (3) | 0.0063 (3) | −0.0004 (3) |
C21 | 0.0220 (5) | 0.0418 (7) | 0.0282 (5) | 0.0008 (5) | 0.0092 (4) | 0.0185 (5) |
C22 | 0.0219 (5) | 0.0267 (5) | 0.0157 (4) | 0.0015 (4) | 0.0079 (3) | 0.0021 (3) |
O1—C1 | 1.3544 (11) | C9—C10 | 1.3858 (14) |
O1—H1O1 | 0.8632 | C9—H9A | 0.9299 |
O2—C4 | 1.3729 (11) | C10—C11 | 1.3898 (14) |
O2—C21 | 1.4253 (14) | C10—H10A | 0.9300 |
O3—C20 | 1.3567 (12) | C11—C12 | 1.3893 (14) |
O3—H1O3 | 0.8989 | C11—H11A | 0.9300 |
O4—C17 | 1.3702 (12) | C12—C13 | 1.4038 (13) |
O4—C22 | 1.4247 (13) | C12—H12A | 0.9299 |
N1—C7 | 1.2921 (12) | C14—C15 | 1.4511 (12) |
N1—C8 | 1.4091 (12) | C14—H14A | 0.9300 |
N2—C14 | 1.2877 (12) | C15—C16 | 1.4028 (13) |
N2—C13 | 1.4133 (12) | C15—C20 | 1.4046 (13) |
C1—C2 | 1.3939 (13) | C16—C17 | 1.3869 (12) |
C1—C6 | 1.4080 (13) | C16—H16A | 0.9299 |
C2—C3 | 1.3804 (13) | C17—C18 | 1.3972 (14) |
C2—H2A | 0.9301 | C18—C19 | 1.3838 (14) |
C3—C4 | 1.4040 (13) | C18—H18A | 0.9301 |
C3—H3A | 0.9300 | C19—C20 | 1.4010 (13) |
C4—C5 | 1.3819 (13) | C19—H19A | 0.9300 |
C5—C6 | 1.4116 (13) | C21—H21A | 0.9600 |
C5—H5A | 0.9301 | C21—H21B | 0.9600 |
C6—C7 | 1.4487 (13) | C21—H21C | 0.9600 |
C7—H7A | 0.9300 | C22—H22A | 0.9600 |
C8—C9 | 1.4047 (13) | C22—H22B | 0.9600 |
C8—C13 | 1.4067 (13) | C22—H22C | 0.9600 |
C1—O1—H1O1 | 105.1 | C11—C12—C13 | 120.69 (9) |
C4—O2—C21 | 116.75 (8) | C11—C12—H12A | 119.7 |
C20—O3—H1O3 | 107.5 | C13—C12—H12A | 119.7 |
C17—O4—C22 | 115.70 (7) | C12—C13—C8 | 119.18 (8) |
C7—N1—C8 | 120.23 (8) | C12—C13—N2 | 123.15 (8) |
C14—N2—C13 | 119.65 (8) | C8—C13—N2 | 117.66 (8) |
O1—C1—C2 | 118.57 (8) | N2—C14—C15 | 122.02 (8) |
O1—C1—C6 | 121.72 (8) | N2—C14—H14A | 119.0 |
C2—C1—C6 | 119.70 (8) | C15—C14—H14A | 119.0 |
C3—C2—C1 | 119.98 (8) | C16—C15—C20 | 119.82 (8) |
C3—C2—H2A | 120.0 | C16—C15—C14 | 118.48 (8) |
C1—C2—H2A | 120.0 | C20—C15—C14 | 121.69 (8) |
C2—C3—C4 | 121.04 (9) | C17—C16—C15 | 120.62 (9) |
C2—C3—H3A | 119.5 | C17—C16—H16A | 119.7 |
C4—C3—H3A | 119.5 | C15—C16—H16A | 119.7 |
O2—C4—C5 | 125.26 (9) | O4—C17—C16 | 123.95 (9) |
O2—C4—C3 | 115.23 (8) | O4—C17—C18 | 116.73 (8) |
C5—C4—C3 | 119.50 (8) | C16—C17—C18 | 119.31 (9) |
C4—C5—C6 | 120.11 (8) | C19—C18—C17 | 120.66 (9) |
C4—C5—H5A | 119.9 | C19—C18—H18A | 119.7 |
C6—C5—H5A | 119.9 | C17—C18—H18A | 119.7 |
C1—C6—C5 | 119.61 (8) | C18—C19—C20 | 120.52 (9) |
C1—C6—C7 | 120.93 (8) | C18—C19—H19A | 119.7 |
C5—C6—C7 | 119.35 (8) | C20—C19—H19A | 119.7 |
N1—C7—C6 | 121.35 (8) | O3—C20—C19 | 119.07 (8) |
N1—C7—H7A | 119.3 | O3—C20—C15 | 121.89 (8) |
C6—C7—H7A | 119.3 | C19—C20—C15 | 119.03 (9) |
C9—C8—C13 | 119.26 (8) | O2—C21—H21A | 109.5 |
C9—C8—N1 | 121.69 (8) | O2—C21—H21B | 109.5 |
C13—C8—N1 | 118.95 (8) | H21A—C21—H21B | 109.5 |
C10—C9—C8 | 120.77 (9) | O2—C21—H21C | 109.5 |
C10—C9—H9A | 119.6 | H21A—C21—H21C | 109.5 |
C8—C9—H9A | 119.6 | H21B—C21—H21C | 109.5 |
C9—C10—C11 | 119.99 (9) | O4—C22—H22A | 109.5 |
C9—C10—H10A | 120.0 | O4—C22—H22B | 109.5 |
C11—C10—H10A | 120.0 | H22A—C22—H22B | 109.5 |
C12—C11—C10 | 120.03 (9) | O4—C22—H22C | 109.5 |
C12—C11—H11A | 120.0 | H22A—C22—H22C | 109.5 |
C10—C11—H11A | 120.0 | H22B—C22—H22C | 109.5 |
O1—C1—C2—C3 | 179.42 (9) | C11—C12—C13—N2 | 176.98 (9) |
C6—C1—C2—C3 | 0.79 (14) | C9—C8—C13—C12 | 1.49 (14) |
C1—C2—C3—C4 | 1.13 (15) | N1—C8—C13—C12 | −175.00 (9) |
C21—O2—C4—C5 | 1.54 (16) | C9—C8—C13—N2 | −178.22 (8) |
C21—O2—C4—C3 | −179.11 (10) | N1—C8—C13—N2 | 5.30 (13) |
C2—C3—C4—O2 | 178.97 (9) | C14—N2—C13—C12 | −22.97 (14) |
C2—C3—C4—C5 | −1.64 (15) | C14—N2—C13—C8 | 156.72 (9) |
O2—C4—C5—C6 | 179.54 (9) | C13—N2—C14—C15 | 178.91 (8) |
C3—C4—C5—C6 | 0.22 (15) | N2—C14—C15—C16 | −174.80 (9) |
O1—C1—C6—C5 | 179.24 (9) | N2—C14—C15—C20 | 5.98 (14) |
C2—C1—C6—C5 | −2.18 (14) | C20—C15—C16—C17 | −0.26 (14) |
O1—C1—C6—C7 | −4.52 (14) | C14—C15—C16—C17 | −179.49 (9) |
C2—C1—C6—C7 | 174.06 (9) | C22—O4—C17—C16 | 6.82 (14) |
C4—C5—C6—C1 | 1.67 (14) | C22—O4—C17—C18 | −173.15 (9) |
C4—C5—C6—C7 | −174.63 (9) | C15—C16—C17—O4 | −178.41 (9) |
C8—N1—C7—C6 | −171.09 (8) | C15—C16—C17—C18 | 1.56 (14) |
C1—C6—C7—N1 | 1.04 (14) | O4—C17—C18—C19 | 178.40 (9) |
C5—C6—C7—N1 | 177.29 (9) | C16—C17—C18—C19 | −1.57 (15) |
C7—N1—C8—C9 | 31.92 (13) | C17—C18—C19—C20 | 0.27 (15) |
C7—N1—C8—C13 | −151.68 (9) | C18—C19—C20—O3 | 179.90 (9) |
C13—C8—C9—C10 | 1.17 (14) | C18—C19—C20—C15 | 1.03 (15) |
N1—C8—C9—C10 | 177.55 (9) | C16—C15—C20—O3 | −179.87 (9) |
C8—C9—C10—C11 | −2.66 (16) | C14—C15—C20—O3 | −0.66 (14) |
C9—C10—C11—C12 | 1.44 (16) | C16—C15—C20—C19 | −1.03 (14) |
C10—C11—C12—C13 | 1.25 (16) | C14—C15—C20—C19 | 178.18 (9) |
C11—C12—C13—C8 | −2.70 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.86 | 1.78 | 2.5811 (13) | 153 |
O3—H1O3···N2 | 0.90 | 1.82 | 2.6285 (14) | 148 |
C7—H7A···Cg2i | 0.93 | 2.82 | 3.2893 (11) | 112 |
C22—H22C···Cg1i | 0.96 | 2.84 | 3.7312 (12) | 155 |
Symmetry code: (i) x, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H20N2O4 |
Mr | 376.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.6772 (3), 13.8721 (3), 13.1182 (3) |
β (°) | 119.875 (2) |
V (Å3) | 1842.60 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.57 × 0.47 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.948, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36710, 8095, 6228 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.807 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.154, 1.04 |
No. of reflections | 8095 |
No. of parameters | 275 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.33 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.86 | 1.7829 | 2.5811 (13) | 153 |
O3—H1O3···N2 | 0.90 | 1.8211 | 2.6285 (14) | 148 |
C7—H7A···Cg2i | 0.93 | 2.8197 | 3.2893 (11) | 112 |
C22—H22C···Cg1i | 0.96 | 2.8378 | 3.7312 (12) | 155 |
Symmetry code: (i) x, −y−1/2, z−1/2. |
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Schiff base compounds have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, such as anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). We have previously reported the crystal structures of Schiff base ligands which are 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a), 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b) and 5,5'-dimethoxy-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007). As an extension of our investigations of Schiff base ligands and complexes, the title compound, (I), was synthesized by the reaction of o-phenylenediamine with 5-methoxysalicylaldehyde, and its crystal structure is reported here.
The structure of the title compound is not planar. The orientations of the C1–C6 and C15–C20 benzene rings respect to the o-phenylenediamine unit are indicated by the dihedral angles of 36.35 (5) and 17.81 (5)°, respectively. The C1–C6 and C15–C20 benzene rings makes the dihedral angle of 43.94 (5)°. The two methoxy groups are planarly attached to the C1–C6 and C15–C20 benzene rings. The C8/N1/C7/C6 unit is not planar as indicated by the torsion angles C8/N1/C7/C6 = -171.09 (8)° while the C13/N2/C14/C15 unit is planarly attached with the torsion angle of 178.91 (8)°. The orientations of these units with respect to the o-phenylenediamine ring are shown by the torsion angles C7/N1/C8/C9 = 31.92 (13)° and C14/N2/C13/C12 = -22.97 (14)°.
The two intramolecular hydrogen bonds, O1—H1O1···N1 and O3—H1O3···N2 generate S(6) ring motifs (Bernstein et al., 1995). Bond lengths and angles in (I) are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Eltayeb et al., 2007; Eltayeb et al., 2007a,b).
In the crystal, the molecules are arranged into chains along the c axis. These chains form molecular sheets parallel to the ac plane (Fig. 2). The crystal is stabilized by O—H···N intramolecular hydrogen bonds (Table 1) and further stabilized by C—H···π interactions (Table 1); Cg1 and Cg2 are the centroids of C8–C13 and C15–C20 benzene rings, respectively.