organic compounds
2,4-Dibromo-6-[(2-hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dienone
aDepartment of Chemistry, Rajshahi University of Engineering & Technology, Rajshahi-6204, Bangladesh, bDepartment of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh, and cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
*Correspondence e-mail: chansheikh@yahoo.com
The new bromo-substituted title compound, C14H11Br2NO2, was synthesized by the condensation of 3,5-dibromosalicylaldehyde and 2-amino-4-methyl phenol. The consists of two crystallographically independent molecules (A and B), which are related to each other by a pseudo-inversion centre. Both molecules are almost planar; dihedral angles between the two benzene rings are 11.40 (11)° for A and 3.05 (12)° for B. In each molecule, there is an intramolecular N—H⋯O hydrogen bond with an S(6) ring motif. In the crystal, two independent molecules are linked by O—H⋯O hydrogen bonds, forming a pseudo-inversion A–B dimer.
Keywords: crystal structure; Schiff base; hydrogen bonding.
CCDC reference: 1814765
Structure description
Organic compounds containing N and O donor atoms are widely used as ligands (Dong et al., 2015; Khalaji et al., 2015; de Blas et al., 1991) and their metal complexes have received considerable attention for their possible bioactivities (Zhang et al., 2012; Khandar et al., 2010). In addition, such compounds also containing halogen atoms have been shown to have attractive biological properties (Dong et al., 2015).
The . The bond lengths of both molecules are almost same and within normal ranges, but the conformations are slightly different. The lengths of C2—O1 and C16—O3 correspond to a C=O double bond, while C9—O2 and C23—O4 are single C—O bonds (Xu et al., 2007). The NH group in each molecule forms an intramolecular N—H⋯O hydrogen bond (Fig. 1 and Table 1).
of the title compound consists of two independent molecules as shown in Fig. 1
|
In the crystal, the two independent molecules are linked via two O—H⋯O hydrogen bonds, forming a pseudo-inversion dimer with an R22(18) ring motif (Fig. 1 and Table 1).
Synthesis and crystallization
A saturated ethanolic solution of 2-amino-4-methyl phenol (123 mg, 1 mmol) was added dropwise to a saturated ethanolic solution of 3,5-dibromosalicylaldehyde (280 mg, 1 mmol) with continuous stirring at 60°C. The mixture was heated with continuous stirring whereupon a precipitate was formed. The mixture was stirred for a further hour at room temperature. The resulting orange solid product was collected by filtration, washed several times with hot ethanol and dried in a vacuum (300 mg, 78%). Orange single crystals were obtained by slow evaporation from an ethanol/acetonitrile (5:1) solution at room temperature over 20 days (m.p. 190°C).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1814765
https://doi.org/10.1107/S2414314618003887/is4026sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618003887/is4026Isup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618003887/is4026Isup3.cml
Cell
RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2017); software used to prepare material for publication: CrystalStructure (Rigaku, 2017).C14H11Br2NO2 | F(000) = 1504.00 |
Mr = 385.05 | Dx = 1.946 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
a = 16.7219 (3) Å | Cell parameters from 27726 reflections |
b = 6.90389 (13) Å | θ = 3.0–68.2° |
c = 23.0811 (4) Å | µ = 7.81 mm−1 |
β = 99.502 (7)° | T = 173 K |
V = 2628.06 (10) Å3 | Platelet, orange |
Z = 8 | 0.36 × 0.29 × 0.08 mm |
Rigaku R-AXIS RAPID diffractometer | 4558 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.048 |
ω scans | θmax = 68.2°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→20 |
Tmin = 0.239, Tmax = 0.535 | k = −8→8 |
28830 measured reflections | l = −27→27 |
4799 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0323P)2 + 3.250P] where P = (Fo2 + 2Fc2)/3 |
4799 reflections | (Δ/σ)max = 0.004 |
361 parameters | Δρmax = 0.99 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Br1 | −0.01727 (2) | 0.20364 (5) | 0.64304 (2) | 0.03261 (10) | |
Br2 | 0.24115 (2) | 0.12206 (6) | 0.51554 (2) | 0.03943 (11) | |
Br3 | 0.25614 (2) | 0.09612 (5) | 1.09293 (2) | 0.03620 (10) | |
Br4 | −0.01488 (2) | 0.11048 (5) | 1.20799 (2) | 0.03135 (9) | |
O1 | 0.12485 (11) | 0.2391 (3) | 0.74614 (8) | 0.0298 (4) | |
O2 | 0.21228 (12) | 0.1592 (3) | 0.89639 (9) | 0.0347 (5) | |
O3 | 0.12662 (11) | 0.2105 (3) | 0.98606 (8) | 0.0295 (4) | |
O4 | 0.04812 (12) | 0.3579 (3) | 0.83675 (9) | 0.0325 (5) | |
N1 | 0.27421 (14) | 0.1839 (3) | 0.79845 (9) | 0.0231 (5) | |
N2 | −0.01980 (14) | 0.2985 (3) | 0.93165 (10) | 0.0231 (5) | |
C1 | 0.23343 (16) | 0.1772 (4) | 0.69402 (11) | 0.0229 (5) | |
C2 | 0.14904 (16) | 0.2072 (4) | 0.69752 (11) | 0.0230 (5) | |
C3 | 0.09544 (15) | 0.1935 (4) | 0.64211 (11) | 0.0231 (5) | |
C4 | 0.12240 (16) | 0.1692 (4) | 0.58993 (12) | 0.0258 (6) | |
H4A | 0.084848 | 0.163499 | 0.554274 | 0.031* | |
C5 | 0.20591 (16) | 0.1527 (4) | 0.58916 (11) | 0.0250 (6) | |
C6 | 0.26057 (16) | 0.1522 (4) | 0.63966 (12) | 0.0248 (6) | |
H6 | 0.316657 | 0.135172 | 0.638484 | 0.030* | |
C7 | 0.29174 (16) | 0.1680 (4) | 0.74565 (11) | 0.0242 (6) | |
H7 | 0.346874 | 0.149222 | 0.741733 | 0.029* | |
C8 | 0.32862 (16) | 0.1779 (4) | 0.85205 (11) | 0.0231 (5) | |
C9 | 0.29418 (16) | 0.1666 (4) | 0.90288 (12) | 0.0255 (6) | |
C10 | 0.34561 (18) | 0.1645 (5) | 0.95692 (12) | 0.0321 (7) | |
H10 | 0.323451 | 0.156331 | 0.992180 | 0.039* | |
C11 | 0.42851 (17) | 0.1742 (5) | 0.95951 (12) | 0.0315 (6) | |
H11 | 0.462526 | 0.173001 | 0.996797 | 0.038* | |
C12 | 0.46372 (17) | 0.1858 (4) | 0.90902 (12) | 0.0278 (6) | |
C13 | 0.41242 (16) | 0.1874 (4) | 0.85515 (12) | 0.0242 (6) | |
H13 | 0.434787 | 0.195000 | 0.819967 | 0.029* | |
C14 | 0.55430 (17) | 0.1992 (5) | 0.91222 (14) | 0.0367 (7) | |
H14A | 0.580797 | 0.101170 | 0.939574 | 0.044* | |
H14B | 0.572862 | 0.328325 | 0.926028 | 0.044* | |
H14C | 0.568130 | 0.176676 | 0.873133 | 0.044* | |
C15 | 0.01183 (16) | 0.2188 (4) | 1.03431 (11) | 0.0231 (6) | |
C16 | 0.09673 (16) | 0.1904 (4) | 1.03296 (11) | 0.0226 (5) | |
C17 | 0.14371 (16) | 0.1393 (4) | 1.08883 (12) | 0.0240 (6) | |
C18 | 0.11088 (17) | 0.1191 (4) | 1.13890 (12) | 0.0252 (6) | |
H18 | 0.144597 | 0.085854 | 1.174796 | 0.030* | |
C19 | 0.02747 (16) | 0.1473 (4) | 1.13744 (11) | 0.0235 (6) | |
C20 | −0.02172 (16) | 0.1947 (4) | 1.08629 (12) | 0.0245 (6) | |
H20 | −0.078274 | 0.211589 | 1.085518 | 0.029* | |
C21 | −0.04189 (16) | 0.2698 (4) | 0.98261 (11) | 0.0244 (6) | |
H21 | −0.097709 | 0.284149 | 0.985166 | 0.029* | |
C22 | −0.07113 (16) | 0.3483 (4) | 0.87846 (11) | 0.0222 (5) | |
C23 | −0.03394 (16) | 0.3733 (4) | 0.82909 (12) | 0.0254 (6) | |
C24 | −0.08220 (18) | 0.4147 (4) | 0.77557 (12) | 0.0300 (6) | |
H24 | −0.058047 | 0.430591 | 0.741398 | 0.036* | |
C25 | −0.16540 (17) | 0.4330 (4) | 0.77181 (12) | 0.0301 (6) | |
H25 | −0.197437 | 0.461047 | 0.734813 | 0.036* | |
C26 | −0.20333 (17) | 0.4115 (4) | 0.82072 (12) | 0.0266 (6) | |
C27 | −0.15469 (16) | 0.3695 (4) | 0.87419 (12) | 0.0240 (6) | |
H27 | −0.178942 | 0.354950 | 0.908375 | 0.029* | |
C28 | −0.29388 (17) | 0.4308 (5) | 0.81661 (14) | 0.0361 (7) | |
H28A | −0.307472 | 0.441898 | 0.856187 | 0.043* | |
H28B | −0.320532 | 0.316250 | 0.797111 | 0.043* | |
H28C | −0.312521 | 0.546832 | 0.793864 | 0.043* | |
H1 | 0.227 (2) | 0.199 (5) | 0.8001 (14) | 0.036 (10)* | |
H2 | 0.193 (2) | 0.164 (6) | 0.9303 (18) | 0.061 (12)* | |
H2A | 0.028 (2) | 0.284 (5) | 0.9301 (14) | 0.031 (9)* | |
H4 | 0.063 (2) | 0.328 (5) | 0.8042 (15) | 0.041 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01857 (15) | 0.0492 (2) | 0.03065 (17) | −0.00132 (12) | 0.00568 (11) | −0.00265 (13) |
Br2 | 0.02797 (17) | 0.0714 (3) | 0.02070 (16) | 0.00151 (15) | 0.00913 (12) | 0.00201 (14) |
Br3 | 0.02106 (16) | 0.0624 (2) | 0.02539 (16) | 0.00287 (13) | 0.00467 (12) | 0.00489 (14) |
Br4 | 0.03446 (18) | 0.03847 (19) | 0.02417 (16) | 0.00327 (12) | 0.01380 (12) | 0.00366 (12) |
O1 | 0.0220 (10) | 0.0471 (12) | 0.0215 (9) | 0.0004 (9) | 0.0077 (7) | 0.0000 (9) |
O2 | 0.0206 (10) | 0.0570 (14) | 0.0280 (11) | 0.0031 (9) | 0.0080 (8) | 0.0017 (10) |
O3 | 0.0234 (10) | 0.0457 (12) | 0.0202 (9) | −0.0010 (9) | 0.0065 (7) | 0.0025 (9) |
O4 | 0.0231 (10) | 0.0467 (13) | 0.0291 (11) | 0.0026 (9) | 0.0088 (8) | −0.0018 (10) |
N1 | 0.0182 (12) | 0.0292 (13) | 0.0215 (12) | 0.0002 (10) | 0.0025 (9) | 0.0019 (9) |
N2 | 0.0183 (12) | 0.0266 (12) | 0.0242 (12) | 0.0004 (9) | 0.0028 (9) | −0.0009 (9) |
C1 | 0.0227 (13) | 0.0235 (14) | 0.0229 (13) | −0.0005 (11) | 0.0050 (10) | 0.0025 (11) |
C2 | 0.0230 (13) | 0.0230 (14) | 0.0237 (13) | −0.0021 (11) | 0.0061 (10) | 0.0025 (11) |
C3 | 0.0180 (13) | 0.0256 (14) | 0.0261 (14) | −0.0005 (10) | 0.0045 (10) | 0.0018 (11) |
C4 | 0.0253 (14) | 0.0293 (14) | 0.0219 (13) | 0.0004 (11) | 0.0014 (10) | 0.0016 (11) |
C5 | 0.0259 (14) | 0.0332 (15) | 0.0171 (12) | −0.0004 (12) | 0.0074 (10) | 0.0026 (11) |
C6 | 0.0199 (13) | 0.0302 (14) | 0.0254 (14) | 0.0002 (11) | 0.0065 (10) | 0.0036 (12) |
C7 | 0.0216 (13) | 0.0254 (14) | 0.0258 (14) | −0.0004 (11) | 0.0046 (10) | 0.0010 (11) |
C8 | 0.0220 (13) | 0.0255 (14) | 0.0214 (13) | −0.0001 (11) | 0.0028 (10) | 0.0024 (11) |
C9 | 0.0234 (14) | 0.0295 (14) | 0.0246 (14) | 0.0020 (11) | 0.0069 (11) | 0.0023 (11) |
C10 | 0.0314 (16) | 0.0433 (18) | 0.0221 (14) | 0.0035 (13) | 0.0058 (11) | 0.0041 (13) |
C11 | 0.0287 (15) | 0.0405 (17) | 0.0231 (14) | −0.0002 (13) | −0.0027 (11) | 0.0032 (12) |
C12 | 0.0240 (14) | 0.0293 (15) | 0.0287 (14) | −0.0006 (11) | 0.0004 (11) | 0.0017 (12) |
C13 | 0.0223 (14) | 0.0288 (14) | 0.0218 (13) | −0.0005 (11) | 0.0046 (10) | 0.0032 (11) |
C14 | 0.0236 (15) | 0.0484 (19) | 0.0360 (16) | −0.0030 (13) | −0.0013 (12) | 0.0063 (14) |
C15 | 0.0242 (13) | 0.0219 (13) | 0.0236 (13) | 0.0002 (11) | 0.0055 (10) | −0.0019 (11) |
C16 | 0.0244 (13) | 0.0223 (13) | 0.0217 (13) | −0.0034 (11) | 0.0058 (10) | −0.0016 (11) |
C17 | 0.0206 (13) | 0.0276 (14) | 0.0237 (13) | −0.0021 (11) | 0.0034 (10) | 0.0002 (11) |
C18 | 0.0274 (14) | 0.0286 (15) | 0.0192 (13) | −0.0005 (11) | 0.0033 (10) | −0.0012 (11) |
C19 | 0.0275 (14) | 0.0250 (14) | 0.0192 (13) | 0.0000 (11) | 0.0075 (10) | −0.0015 (11) |
C20 | 0.0218 (13) | 0.0267 (14) | 0.0265 (14) | 0.0018 (11) | 0.0082 (11) | −0.0015 (11) |
C21 | 0.0233 (13) | 0.0261 (14) | 0.0242 (13) | 0.0015 (11) | 0.0051 (10) | −0.0013 (11) |
C22 | 0.0237 (13) | 0.0214 (13) | 0.0211 (13) | 0.0011 (11) | 0.0025 (10) | −0.0015 (10) |
C23 | 0.0238 (14) | 0.0263 (14) | 0.0267 (14) | 0.0000 (11) | 0.0056 (11) | −0.0045 (11) |
C24 | 0.0344 (16) | 0.0351 (16) | 0.0217 (14) | −0.0008 (13) | 0.0078 (11) | −0.0031 (12) |
C25 | 0.0313 (15) | 0.0322 (16) | 0.0244 (14) | 0.0010 (12) | −0.0027 (11) | −0.0012 (12) |
C26 | 0.0251 (14) | 0.0272 (15) | 0.0268 (14) | −0.0001 (11) | 0.0024 (11) | −0.0020 (11) |
C27 | 0.0239 (14) | 0.0246 (14) | 0.0241 (13) | 0.0010 (11) | 0.0056 (10) | 0.0003 (11) |
C28 | 0.0255 (15) | 0.0438 (18) | 0.0375 (17) | 0.0030 (13) | 0.0010 (12) | 0.0009 (14) |
Br1—C3 | 1.890 (3) | C11—C12 | 1.392 (4) |
Br2—C5 | 1.900 (3) | C11—H11 | 0.9500 |
Br3—C17 | 1.890 (3) | C12—C13 | 1.389 (4) |
Br4—C19 | 1.897 (3) | C12—C14 | 1.507 (4) |
O1—C2 | 1.273 (3) | C13—H13 | 0.9500 |
O2—C9 | 1.354 (3) | C14—H14A | 0.9800 |
O2—H2 | 0.90 (4) | C14—H14B | 0.9800 |
O3—C16 | 1.273 (3) | C14—H14C | 0.9800 |
O4—C23 | 1.358 (3) | C15—C21 | 1.415 (4) |
O4—H4 | 0.86 (3) | C15—C20 | 1.416 (4) |
N1—C7 | 1.304 (3) | C15—C16 | 1.438 (4) |
N1—C8 | 1.410 (3) | C16—C17 | 1.439 (4) |
N1—H1 | 0.80 (3) | C17—C18 | 1.366 (4) |
N2—C21 | 1.305 (3) | C18—C19 | 1.403 (4) |
N2—C22 | 1.419 (3) | C18—H18 | 0.9500 |
N2—H2A | 0.81 (3) | C19—C20 | 1.363 (4) |
C1—C7 | 1.411 (4) | C20—H20 | 0.9500 |
C1—C6 | 1.414 (4) | C21—H21 | 0.9500 |
C1—C2 | 1.442 (4) | C22—C27 | 1.392 (4) |
C2—C3 | 1.439 (4) | C22—C23 | 1.396 (4) |
C3—C4 | 1.364 (4) | C23—C24 | 1.389 (4) |
C4—C5 | 1.404 (4) | C24—C25 | 1.385 (4) |
C4—H4A | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.357 (4) | C25—C26 | 1.391 (4) |
C6—H6 | 0.9500 | C25—H25 | 0.9500 |
C7—H7 | 0.9500 | C26—C27 | 1.392 (4) |
C8—C9 | 1.392 (4) | C26—C28 | 1.507 (4) |
C8—C13 | 1.393 (4) | C27—H27 | 0.9500 |
C9—C10 | 1.393 (4) | C28—H28A | 0.9800 |
C10—C11 | 1.379 (4) | C28—H28B | 0.9800 |
C10—H10 | 0.9500 | C28—H28C | 0.9800 |
C9—O2—H2 | 114 (3) | H14A—C14—H14B | 109.5 |
C23—O4—H4 | 110 (2) | C12—C14—H14C | 109.5 |
C7—N1—C8 | 127.3 (2) | H14A—C14—H14C | 109.5 |
C7—N1—H1 | 115 (2) | H14B—C14—H14C | 109.5 |
C8—N1—H1 | 117 (2) | C21—C15—C20 | 117.3 (2) |
C21—N2—C22 | 126.6 (2) | C21—C15—C16 | 120.5 (2) |
C21—N2—H2A | 117 (2) | C20—C15—C16 | 122.2 (2) |
C22—N2—H2A | 117 (2) | O3—C16—C15 | 122.1 (2) |
C7—C1—C6 | 117.8 (2) | O3—C16—C17 | 123.8 (2) |
C7—C1—C2 | 120.4 (2) | C15—C16—C17 | 114.1 (2) |
C6—C1—C2 | 121.9 (2) | C18—C17—C16 | 123.2 (2) |
O1—C2—C3 | 123.6 (2) | C18—C17—Br3 | 118.5 (2) |
O1—C2—C1 | 122.0 (2) | C16—C17—Br3 | 118.35 (19) |
C3—C2—C1 | 114.4 (2) | C17—C18—C19 | 120.1 (2) |
C4—C3—C2 | 123.0 (2) | C17—C18—H18 | 119.9 |
C4—C3—Br1 | 119.4 (2) | C19—C18—H18 | 119.9 |
C2—C3—Br1 | 117.62 (19) | C20—C19—C18 | 120.6 (2) |
C3—C4—C5 | 119.7 (2) | C20—C19—Br4 | 121.2 (2) |
C3—C4—H4A | 120.2 | C18—C19—Br4 | 118.12 (19) |
C5—C4—H4A | 120.2 | C19—C20—C15 | 119.7 (3) |
C6—C5—C4 | 121.3 (2) | C19—C20—H20 | 120.2 |
C6—C5—Br2 | 120.2 (2) | C15—C20—H20 | 120.2 |
C4—C5—Br2 | 118.44 (19) | N2—C21—C15 | 124.3 (3) |
C5—C6—C1 | 119.5 (2) | N2—C21—H21 | 117.9 |
C5—C6—H6 | 120.2 | C15—C21—H21 | 117.9 |
C1—C6—H6 | 120.2 | C27—C22—C23 | 120.4 (2) |
N1—C7—C1 | 123.7 (3) | C27—C22—N2 | 122.9 (2) |
N1—C7—H7 | 118.2 | C23—C22—N2 | 116.7 (2) |
C1—C7—H7 | 118.2 | O4—C23—C24 | 123.9 (3) |
C9—C8—C13 | 120.8 (2) | O4—C23—C22 | 117.4 (2) |
C9—C8—N1 | 116.4 (2) | C24—C23—C22 | 118.6 (3) |
C13—C8—N1 | 122.8 (2) | C25—C24—C23 | 120.3 (3) |
O2—C9—C8 | 117.4 (2) | C25—C24—H24 | 119.8 |
O2—C9—C10 | 124.2 (2) | C23—C24—H24 | 119.8 |
C8—C9—C10 | 118.4 (3) | C24—C25—C26 | 121.8 (3) |
C11—C10—C9 | 120.4 (3) | C24—C25—H25 | 119.1 |
C11—C10—H10 | 119.8 | C26—C25—H25 | 119.1 |
C9—C10—H10 | 119.8 | C25—C26—C27 | 117.6 (3) |
C10—C11—C12 | 121.8 (3) | C25—C26—C28 | 121.8 (2) |
C10—C11—H11 | 119.1 | C27—C26—C28 | 120.5 (3) |
C12—C11—H11 | 119.1 | C26—C27—C22 | 121.1 (3) |
C13—C12—C11 | 117.8 (3) | C26—C27—H27 | 119.4 |
C13—C12—C14 | 120.7 (3) | C22—C27—H27 | 119.4 |
C11—C12—C14 | 121.5 (3) | C26—C28—H28A | 109.5 |
C12—C13—C8 | 120.9 (2) | C26—C28—H28B | 109.5 |
C12—C13—H13 | 119.6 | H28A—C28—H28B | 109.5 |
C8—C13—H13 | 119.6 | C26—C28—H28C | 109.5 |
C12—C14—H14A | 109.5 | H28A—C28—H28C | 109.5 |
C12—C14—H14B | 109.5 | H28B—C28—H28C | 109.5 |
C7—C1—C2—O1 | 4.8 (4) | C21—C15—C16—O3 | 0.3 (4) |
C6—C1—C2—O1 | −176.5 (3) | C20—C15—C16—O3 | 179.4 (3) |
C7—C1—C2—C3 | −173.9 (3) | C21—C15—C16—C17 | 179.9 (2) |
C6—C1—C2—C3 | 4.8 (4) | C20—C15—C16—C17 | −1.0 (4) |
O1—C2—C3—C4 | 176.5 (3) | O3—C16—C17—C18 | 179.7 (3) |
C1—C2—C3—C4 | −4.8 (4) | C15—C16—C17—C18 | 0.1 (4) |
O1—C2—C3—Br1 | −5.1 (4) | O3—C16—C17—Br3 | −0.8 (4) |
C1—C2—C3—Br1 | 173.57 (19) | C15—C16—C17—Br3 | 179.56 (19) |
C2—C3—C4—C5 | 1.3 (4) | C16—C17—C18—C19 | 0.4 (4) |
Br1—C3—C4—C5 | −177.1 (2) | Br3—C17—C18—C19 | −179.1 (2) |
C3—C4—C5—C6 | 2.8 (4) | C17—C18—C19—C20 | 0.1 (4) |
C3—C4—C5—Br2 | −179.3 (2) | C17—C18—C19—Br4 | 178.4 (2) |
C4—C5—C6—C1 | −2.8 (4) | C18—C19—C20—C15 | −1.0 (4) |
Br2—C5—C6—C1 | 179.3 (2) | Br4—C19—C20—C15 | −179.2 (2) |
C7—C1—C6—C5 | 177.5 (3) | C21—C15—C20—C19 | −179.4 (3) |
C2—C1—C6—C5 | −1.2 (4) | C16—C15—C20—C19 | 1.5 (4) |
C8—N1—C7—C1 | −179.5 (3) | C22—N2—C21—C15 | 179.5 (3) |
C6—C1—C7—N1 | −178.2 (3) | C20—C15—C21—N2 | 179.4 (3) |
C2—C1—C7—N1 | 0.5 (4) | C16—C15—C21—N2 | −1.5 (4) |
C7—N1—C8—C9 | −169.9 (3) | C21—N2—C22—C27 | −1.3 (4) |
C7—N1—C8—C13 | 11.6 (4) | C21—N2—C22—C23 | 179.6 (3) |
C13—C8—C9—O2 | 179.5 (3) | C27—C22—C23—O4 | 177.6 (2) |
N1—C8—C9—O2 | 1.0 (4) | N2—C22—C23—O4 | −3.3 (4) |
C13—C8—C9—C10 | −0.1 (4) | C27—C22—C23—C24 | −1.6 (4) |
N1—C8—C9—C10 | −178.6 (3) | N2—C22—C23—C24 | 177.5 (2) |
O2—C9—C10—C11 | −179.4 (3) | O4—C23—C24—C25 | −178.3 (3) |
C8—C9—C10—C11 | 0.2 (5) | C22—C23—C24—C25 | 0.8 (4) |
C9—C10—C11—C12 | −0.2 (5) | C23—C24—C25—C26 | 0.2 (5) |
C10—C11—C12—C13 | 0.0 (5) | C24—C25—C26—C27 | −0.3 (4) |
C10—C11—C12—C14 | 179.2 (3) | C24—C25—C26—C28 | −179.8 (3) |
C11—C12—C13—C8 | 0.1 (4) | C25—C26—C27—C22 | −0.5 (4) |
C14—C12—C13—C8 | −179.1 (3) | C28—C26—C27—C22 | 179.0 (3) |
C9—C8—C13—C12 | 0.0 (4) | C23—C22—C27—C26 | 1.4 (4) |
N1—C8—C13—C12 | 178.4 (3) | N2—C22—C27—C26 | −177.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.90 (4) | 1.86 (4) | 2.728 (3) | 163 (4) |
O4—H4···O1 | 0.86 (4) | 1.92 (4) | 2.753 (3) | 164 (3) |
N1—H1···O1 | 0.80 (4) | 1.97 (3) | 2.616 (3) | 139 (3) |
N2—H2A···O3 | 0.81 (3) | 1.99 (3) | 2.632 (3) | 136 (3) |
Acknowledgements
TKP, MDH, MCS and MAA are grateful to the Department of Chemistry, Rajshahi University of Engineering & Technology (RUET) for the provision of laboratory facilities. RM and MCS acknowledge the Center for Environmental Conservation and Research Safety, University of Toyama, Japan for providing facilities for single-crystal X-ray analysis.
References
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Blas, A. de, Bastida, R. & Fucntcs, M. J. (1991). Synth. React. Inorg. Met.-Org. Chem. 21, 1273–1298. CrossRef Web of Science Google Scholar
Dong, Y. L., Li, C., Meng, X. F., Zhou, X. & Ma, J. J. (2015). J. Struct. Chem. 56, 1426–1430. Web of Science CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Khalaji, A. D., Hafez Ghoran, S., Pojarová, M. & Dušek, M. (2015). J. Struct. Chem. 56, 1410–1414. Web of Science CrossRef CAS Google Scholar
Khandar, A. A., Hosseini-Yazdi, S. A., Khatamian, M. & Zarei, S. A. (2010). Polyhedron, 29, 995–1000. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2017). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, T.-T., Xu, X.-Y., Gao, J., Ni, S.-S., Wang, D.-Q., Lu, L.-D., Yang, X.-J. & Wang, X. (2007). J. Struct. Chem. 48, 193–197. Web of Science CrossRef Google Scholar
Zhang, M., Xian, D. M., Li, H. H., Zhang, J. C. & You, Z. L. (2012). Aust. J. Chem. 65, 343–350. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.