organic compounds
N-(4-Methoxybenzoyl)benzenesulfonamide
aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Chemistry, AVK College for Women, Davangere-2, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, dUniversity College of Science, Tumkur University, Tumkur, India, and eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in
In the title compound, C14H13NO4S, the dihedral angle between the aromatic rings is 69.81 (1)°; the dihedral angle between the planes defined by the S—N—C=O segment of the central chain and the sulfonyl benzene ring is 74.91 (1)°. In the crystal, the molecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains running along [100]. The molecules in adjacent chains are linked by weak C—H⋯O interactions, generating R22 (16) dimeric pairs. Weak C—H⋯π interactions connect the double chains into (001) sheets.
CCDC reference: 978142
Related literature
For similar structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010); Sreenivasa et al. (2013).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 978142
10.1107/S1600536814001330/hb7187sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001330/hb7187Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001330/hb7187Isup3.cml
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2009, 2010; Sreenivasa et al., 2013; Gowda et al., 2009), we report here the
of the title compound (I) (Fig 1).The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, benzenesulfonamide and phosphorous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 399 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.
The H atom of the NH group was located in a difference map and later restained to N—H = 0.86 (4) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).
In (I), the dihedral angle between the aromatic rings is 69.81 (1)°. Compared to this, the dihedral angle is 80.3 (1)° in N-(benzoyl)-benzenesulfonamide (II) (Gowda et al., 2009), 68.6 (1)° in N-(4-chlorobenzoyl)-benzenesulfonamide (III) (Suchetan et al., 2009), 71.9 (1)° in N-(4-methylbenzoyl)-benzenesulfonamide (IV) (Suchetan et al., 2010) and 78.62 (16)° in N-(4-methoxybenzoyl)-4-methylbenzenesulfonamide (V) (Sreenivasa et al., 2013). This shows that introducing a substituent into the para position of the benzoyl ring correlates with a decrease of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 74.91 (1)°.
In the crystal, both strong classical N—H···O hydrogen bonds and weaker C—H···O and C—H···Cg interactions are observed. The molecules are linked to one another through strong N1—HN1···O1 hydrogen bonds into C(4) chains running along [100]. The molecules in the adjacent chains are linked through weak C12—H12···O2 interactions, generating R22 (16) dimeric pairs. Combination of the N1—HN1···O1 linked chains and C12—H12···O2 linked dimers form columns along a axis (Figure 2 & 3). The molecules are further connected into C(10) chains running along [010] through C4—H4···Cg interactions (Figure 4) resulting in a two dimensional architecture.
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2009, 2010; Sreenivasa et al., 2013; Gowda et al., 2009), we report here the
of the title compound (I) (Fig 1).In (I), the dihedral angle between the aromatic rings is 69.81 (1)°. Compared to this, the dihedral angle is 80.3 (1)° in N-(benzoyl)-benzenesulfonamide (II) (Gowda et al., 2009), 68.6 (1)° in N-(4-chlorobenzoyl)-benzenesulfonamide (III) (Suchetan et al., 2009), 71.9 (1)° in N-(4-methylbenzoyl)-benzenesulfonamide (IV) (Suchetan et al., 2010) and 78.62 (16)° in N-(4-methoxybenzoyl)-4-methylbenzenesulfonamide (V) (Sreenivasa et al., 2013). This shows that introducing a substituent into the para position of the benzoyl ring correlates with a decrease of the dihedral angle between the aromatic rings. Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S—N—C=O segment in the central chain and the sulfonyl benzene ring being 74.91 (1)°.
In the crystal, both strong classical N—H···O hydrogen bonds and weaker C—H···O and C—H···Cg interactions are observed. The molecules are linked to one another through strong N1—HN1···O1 hydrogen bonds into C(4) chains running along [100]. The molecules in the adjacent chains are linked through weak C12—H12···O2 interactions, generating R22 (16) dimeric pairs. Combination of the N1—HN1···O1 linked chains and C12—H12···O2 linked dimers form columns along a axis (Figure 2 & 3). The molecules are further connected into C(10) chains running along [010] through C4—H4···Cg interactions (Figure 4) resulting in a two dimensional architecture.
For similar structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010); Sreenivasa et al. (2013).
The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, benzenesulfonamide and phosphorous oxychloride (POCl3) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 399 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.
detailsThe H atom of the NH group was located in a difference map and later restained to N—H = 0.86 (4) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).
Data collection: APEX2 (Bruker, 2009); cell
APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Columns generated from the combination of N1—HN1···O1 linked chains and C12—H12···O2 linked dimers in (I) when viewed along a axis. H-atoms not involved in H-bonds are omitted for clarity purpose. | |
Fig. 3. Columns generated from the combination of N1—HN1···O1 linked chains and C12—H12···O2 linked dimers in (I) when viewed down a axis. H-atoms not involved in H-bonds are omitted for clarity purpose. | |
Fig. 4. C4—H4···Cg interaction observed in the structure of (I). Cg is the centroid of the methoxyphenyl ring. |
C14H13NO4S | F(000) = 304 |
Mr = 291.31 | Prism |
Triclinic, P1 | Dx = 1.449 Mg m−3 |
Hall symbol: -P 1 | Melting point: 399 K |
a = 5.3059 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.6343 (10) Å | Cell parameters from 25 reflections |
c = 11.9139 (11) Å | θ = 3.7–64.8° |
α = 89.792 (3)° | µ = 2.28 mm−1 |
β = 87.392 (3)° | T = 293 K |
γ = 83.944 (3)° | Prism, colourless |
V = 667.79 (11) Å3 | 0.37 × 0.26 × 0.20 mm |
Z = 2 |
Bruker APEXII diffractometer | 2076 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Graphite monochromator | θmax = 64.8°, θmin = 3.7° |
phi and φ scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −12→12 |
Tmin = 0.515, Tmax = 0.633 | l = −13→13 |
8561 measured reflections | 3 standard reflections every 120 min |
2168 independent reflections | intensity decay: 1% |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.1013P)2 + 0.1754P] where P = (Fo2 + 2Fc2)/3 |
2168 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 0.33 e Å−3 |
1 restraint | Δρmin = −0.84 e Å−3 |
C14H13NO4S | γ = 83.944 (3)° |
Mr = 291.31 | V = 667.79 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.3059 (5) Å | Cu Kα radiation |
b = 10.6343 (10) Å | µ = 2.28 mm−1 |
c = 11.9139 (11) Å | T = 293 K |
α = 89.792 (3)° | 0.37 × 0.26 × 0.20 mm |
β = 87.392 (3)° |
Bruker APEXII diffractometer | 2076 reflections with I > 2σ(I) |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | Rint = 0.049 |
Tmin = 0.515, Tmax = 0.633 | 3 standard reflections every 120 min |
8561 measured reflections | intensity decay: 1% |
2168 independent reflections |
R[F2 > 2σ(F2)] = 0.068 | 1 restraint |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.33 e Å−3 |
2168 reflections | Δρmin = −0.84 e Å−3 |
186 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.2427 (3) | 0.36646 (17) | 0.44504 (16) | 0.0596 (5) | |
N1 | 0.6766 (4) | 0.40318 (19) | 0.36803 (17) | 0.0478 (5) | |
O3 | 0.4534 (3) | 0.39943 (16) | 0.21164 (15) | 0.0559 (5) | |
O4 | 1.1816 (4) | 0.81223 (19) | 0.06023 (17) | 0.0695 (6) | |
C13 | 0.9563 (4) | 0.5966 (2) | 0.26610 (18) | 0.0421 (5) | |
H13 | 0.9898 | 0.5737 | 0.3398 | 0.051* | |
C7 | 0.6197 (4) | 0.4435 (2) | 0.25993 (19) | 0.0424 (5) | |
O2 | 0.6259 (4) | 0.30297 (18) | 0.54898 (15) | 0.0624 (5) | |
C9 | 0.7269 (6) | 0.5777 (3) | 0.1010 (2) | 0.0609 (7) | |
H9 | 0.6030 | 0.5417 | 0.0631 | 0.073* | |
C1 | 0.5310 (4) | 0.1655 (2) | 0.37956 (18) | 0.0405 (5) | |
C12 | 1.0878 (4) | 0.6857 (2) | 0.2130 (2) | 0.0475 (6) | |
H12 | 1.2101 | 0.7227 | 0.2512 | 0.057* | |
C8 | 0.7732 (4) | 0.5405 (2) | 0.21008 (18) | 0.0402 (5) | |
C11 | 1.0410 (5) | 0.7213 (2) | 0.1032 (2) | 0.0472 (6) | |
C5 | 0.3772 (5) | 0.0164 (2) | 0.2584 (2) | 0.0564 (6) | |
H5 | 0.2579 | −0.0048 | 0.2089 | 0.068* | |
C3 | 0.7531 (5) | −0.0405 (3) | 0.3552 (3) | 0.0649 (8) | |
H3 | 0.8890 | −0.0996 | 0.3709 | 0.078* | |
C4 | 0.5776 (5) | −0.0707 (2) | 0.2829 (2) | 0.0547 (6) | |
H4 | 0.5930 | −0.1504 | 0.2500 | 0.066* | |
C2 | 0.7307 (5) | 0.0778 (3) | 0.4055 (2) | 0.0574 (6) | |
H2 | 0.8487 | 0.0979 | 0.4562 | 0.069* | |
C14 | 1.1590 (10) | 0.8451 (4) | −0.0546 (3) | 0.0986 (13) | |
H14A | 1.2092 | 0.7720 | −0.1005 | 0.148* | |
H14B | 1.2665 | 0.9100 | −0.0734 | 0.148* | |
H14C | 0.9860 | 0.8757 | −0.0676 | 0.148* | |
C6 | 0.3516 (4) | 0.1360 (2) | 0.3071 (2) | 0.0498 (6) | |
H6 | 0.2157 | 0.1948 | 0.2910 | 0.060* | |
C10 | 0.8596 (6) | 0.6669 (3) | 0.0467 (2) | 0.0635 (7) | |
H10 | 0.8267 | 0.6899 | −0.0270 | 0.076* | |
S1 | 0.50162 (10) | 0.31426 (5) | 0.44550 (4) | 0.0452 (3) | |
HN1 | 0.808 (6) | 0.419 (4) | 0.397 (3) | 0.091 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0540 (10) | 0.0592 (10) | 0.0642 (11) | −0.0033 (8) | 0.0092 (8) | −0.0138 (8) |
N1 | 0.0543 (12) | 0.0501 (11) | 0.0432 (11) | −0.0222 (9) | −0.0093 (9) | 0.0000 (8) |
O3 | 0.0563 (10) | 0.0581 (10) | 0.0573 (10) | −0.0197 (8) | −0.0149 (8) | −0.0071 (8) |
O4 | 0.0829 (14) | 0.0677 (12) | 0.0582 (12) | −0.0183 (10) | 0.0158 (10) | 0.0140 (9) |
C13 | 0.0460 (12) | 0.0463 (11) | 0.0348 (11) | −0.0079 (9) | −0.0035 (9) | −0.0026 (9) |
C7 | 0.0460 (12) | 0.0400 (11) | 0.0419 (12) | −0.0065 (9) | −0.0039 (9) | −0.0105 (9) |
O2 | 0.0851 (13) | 0.0689 (11) | 0.0385 (9) | −0.0294 (10) | −0.0111 (9) | −0.0024 (8) |
C9 | 0.0753 (18) | 0.0729 (17) | 0.0393 (13) | −0.0241 (13) | −0.0155 (12) | −0.0048 (11) |
C1 | 0.0383 (11) | 0.0445 (11) | 0.0403 (11) | −0.0142 (8) | 0.0036 (8) | −0.0022 (8) |
C12 | 0.0477 (12) | 0.0519 (13) | 0.0445 (12) | −0.0126 (10) | −0.0019 (9) | −0.0006 (10) |
C8 | 0.0427 (11) | 0.0417 (11) | 0.0361 (11) | −0.0047 (9) | 0.0001 (9) | −0.0081 (8) |
C11 | 0.0523 (13) | 0.0460 (12) | 0.0418 (12) | −0.0035 (10) | 0.0118 (10) | −0.0010 (9) |
C5 | 0.0568 (14) | 0.0537 (14) | 0.0624 (16) | −0.0215 (11) | −0.0058 (11) | −0.0110 (11) |
C3 | 0.0542 (15) | 0.0558 (15) | 0.083 (2) | 0.0029 (12) | −0.0004 (14) | −0.0073 (13) |
C4 | 0.0572 (14) | 0.0445 (12) | 0.0628 (16) | −0.0153 (10) | 0.0159 (12) | −0.0095 (10) |
C2 | 0.0450 (13) | 0.0652 (15) | 0.0628 (15) | −0.0071 (11) | −0.0084 (11) | −0.0083 (12) |
C14 | 0.147 (4) | 0.091 (2) | 0.0561 (19) | −0.018 (2) | 0.032 (2) | 0.0156 (17) |
C6 | 0.0449 (12) | 0.0469 (12) | 0.0598 (14) | −0.0128 (9) | −0.0081 (10) | −0.0050 (10) |
C10 | 0.084 (2) | 0.0740 (17) | 0.0338 (12) | −0.0134 (14) | −0.0043 (12) | 0.0032 (11) |
S1 | 0.0516 (4) | 0.0468 (4) | 0.0393 (4) | −0.0156 (3) | 0.0011 (3) | −0.0074 (2) |
O1—S1 | 1.4264 (19) | C1—S1 | 1.758 (2) |
N1—C7 | 1.392 (3) | C12—C11 | 1.387 (3) |
N1—S1 | 1.646 (2) | C12—H12 | 0.9300 |
N1—HN1 | 0.82 (3) | C11—C10 | 1.376 (4) |
O3—C7 | 1.211 (3) | C5—C4 | 1.376 (4) |
O4—C11 | 1.367 (3) | C5—C6 | 1.390 (4) |
O4—C14 | 1.418 (4) | C5—H5 | 0.9300 |
C13—C12 | 1.371 (3) | C3—C4 | 1.360 (4) |
C13—C8 | 1.389 (3) | C3—C2 | 1.388 (4) |
C13—H13 | 0.9300 | C3—H3 | 0.9300 |
C7—C8 | 1.486 (3) | C4—H4 | 0.9300 |
O2—S1 | 1.4232 (19) | C2—H2 | 0.9300 |
C9—C10 | 1.381 (4) | C14—H14A | 0.9600 |
C9—C8 | 1.382 (3) | C14—H14B | 0.9600 |
C9—H9 | 0.9300 | C14—H14C | 0.9600 |
C1—C6 | 1.375 (3) | C6—H6 | 0.9300 |
C1—C2 | 1.381 (4) | C10—H10 | 0.9300 |
C7—N1—S1 | 123.91 (17) | C4—C3—C2 | 120.4 (2) |
C7—N1—HN1 | 122 (3) | C4—C3—H3 | 119.8 |
S1—N1—HN1 | 114 (3) | C2—C3—H3 | 119.8 |
C11—O4—C14 | 118.2 (3) | C3—C4—C5 | 120.2 (2) |
C12—C13—C8 | 120.1 (2) | C3—C4—H4 | 119.9 |
C12—C13—H13 | 119.9 | C5—C4—H4 | 119.9 |
C8—C13—H13 | 119.9 | C1—C2—C3 | 119.2 (2) |
O3—C7—N1 | 120.0 (2) | C1—C2—H2 | 120.4 |
O3—C7—C8 | 123.6 (2) | C3—C2—H2 | 120.4 |
N1—C7—C8 | 116.42 (19) | O4—C14—H14A | 109.5 |
C10—C9—C8 | 121.9 (2) | O4—C14—H14B | 109.5 |
C10—C9—H9 | 119.1 | H14A—C14—H14B | 109.5 |
C8—C9—H9 | 119.1 | O4—C14—H14C | 109.5 |
C6—C1—C2 | 121.0 (2) | H14A—C14—H14C | 109.5 |
C6—C1—S1 | 120.16 (18) | H14B—C14—H14C | 109.5 |
C2—C1—S1 | 118.81 (18) | C1—C6—C5 | 118.7 (2) |
C13—C12—C11 | 120.9 (2) | C1—C6—H6 | 120.6 |
C13—C12—H12 | 119.5 | C5—C6—H6 | 120.6 |
C11—C12—H12 | 119.5 | C11—C10—C9 | 119.1 (2) |
C9—C8—C13 | 118.3 (2) | C11—C10—H10 | 120.4 |
C9—C8—C7 | 117.3 (2) | C9—C10—H10 | 120.4 |
C13—C8—C7 | 124.4 (2) | O2—S1—O1 | 119.44 (12) |
O4—C11—C10 | 125.0 (2) | O2—S1—N1 | 103.74 (11) |
O4—C11—C12 | 115.3 (2) | O1—S1—N1 | 109.21 (11) |
C10—C11—C12 | 119.6 (2) | O2—S1—C1 | 108.88 (11) |
C4—C5—C6 | 120.5 (2) | O1—S1—C1 | 108.65 (10) |
C4—C5—H5 | 119.7 | N1—S1—C1 | 106.11 (10) |
C6—C5—H5 | 119.7 | ||
S1—N1—C7—O3 | −10.3 (3) | S1—C1—C2—C3 | 179.0 (2) |
S1—N1—C7—C8 | 169.94 (15) | C4—C3—C2—C1 | −1.4 (4) |
C8—C13—C12—C11 | 0.0 (3) | C2—C1—C6—C5 | −1.2 (4) |
C10—C9—C8—C13 | 1.0 (4) | S1—C1—C6—C5 | −178.49 (18) |
C10—C9—C8—C7 | −179.8 (2) | C4—C5—C6—C1 | 0.4 (4) |
C12—C13—C8—C9 | −0.6 (3) | O4—C11—C10—C9 | −178.6 (2) |
C12—C13—C8—C7 | −179.8 (2) | C12—C11—C10—C9 | 0.1 (4) |
O3—C7—C8—C9 | −2.4 (3) | C8—C9—C10—C11 | −0.7 (4) |
N1—C7—C8—C9 | 177.3 (2) | C7—N1—S1—O2 | −177.30 (19) |
O3—C7—C8—C13 | 176.8 (2) | C7—N1—S1—O1 | −48.9 (2) |
N1—C7—C8—C13 | −3.5 (3) | C7—N1—S1—C1 | 68.0 (2) |
C14—O4—C11—C10 | −6.6 (4) | C6—C1—S1—O2 | 153.0 (2) |
C14—O4—C11—C12 | 174.7 (3) | C2—C1—S1—O2 | −24.3 (2) |
C13—C12—C11—O4 | 179.0 (2) | C6—C1—S1—O1 | 21.4 (2) |
C13—C12—C11—C10 | 0.2 (4) | C2—C1—S1—O1 | −155.9 (2) |
C2—C3—C4—C5 | 0.6 (4) | C6—C1—S1—N1 | −95.9 (2) |
C6—C5—C4—C3 | −0.1 (4) | C2—C1—S1—N1 | 86.8 (2) |
C6—C1—C2—C3 | 1.7 (4) |
Cg is the centroid of the methoxybenzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1i | 0.83 (3) | 2.41 (3) | 3.1662 (3) | 153 |
C12—H12···O2ii | 0.93 | 2.58 | 3.286 (3) | 133 |
C4—H4···Cgiii | 0.93 | 2.90 | 3.7396 | 150 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z. |
Cg is the centroid of the methoxybenzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1i | 0.83 (3) | 2.41 (3) | 3.1662 (3) | 153 |
C12—H12···O2ii | 0.93 | 2.58 | 3.286 (3) | 133 |
C4—H4···Cgiii | 0.93 | 2.90 | 3.7396 | 150 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z. |
Acknowledgements
The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection.
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