


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015006738/tk5362sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006738/tk5362Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015006738/tk5362Isup3.cml |
CCDC reference: 1057743
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.079
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level C PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C11 -C16 1.37 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.617 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 5 Report
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 42 % PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Hetero cyclic compounds of 2-oxo-2H-chromenes display wide range of biological activities such as anti-HIV (Kostova, et al., 2006), anti-cancer (Abdel-Aziz et al.,2013), etc. They also play a significant role as chemical sensors, fluorescent probes and laser dyes (Chandrasekharan et al., 2002). In continuation of our work on 2-oxo-2H-chromene derivatives (Sreenivasa et al., 2013; Palakshamurthy, Sreenivasa et al., 2013; Palakshamurthy, Devarajegowda et al., 2013; Devarajegowda, et al.,2013), in the present work we report the synthesis and crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate (I), an intermediate compound obtained during synthesis of coumarin–based Liquid Crystals (LCs).
The dihedral angle between the coumarin ring and the bromobenzene ring in (I) is 25.85 (10)°. Compared to this, the dihedral angle is 22.95 (11)° in 4'-cyanobiphenyl-4-yl-7-diethylamino-2-oxo-2H-chromene-3-carboxylate (II) (Sreenivasa et al., 2013), 62.97 (2)° in 4-(decyloxy)phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (III) (Palakshamurthy, Sreenivasa et al., 2013), 21.00 (1)° in 4-(octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate (IV) (Palakshamurthy, Devarajegowda et al., 2013) and 54.46 (17)° in 4-[4-(heptyloxy)benzoyloxy] phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (V) (Devarajegowda, et al., 2013). Further, in (I), the torsions C9—C8—C10—O3, O3—C10—O4—C11 and C12—C11—O4—C10 have values 27.6 (4), 6.3 (3) and 124.6 (2)°, respectively.
In the crystal structure, the molecules are connected along [001] via C12—H12···O3 interactions forming C(6) chains (Fig 2., Table 2). Further, neighbouring C(6) chains are interlocked via π···π interactions (Fig. 3), namely, Cg1··· Cg3i [3.7254 (15) Å, i: 1-x, 1/2+y, 1/2-z] and Cg2··· Cg3i,ii [3.7303 (16) and 3.7716 (16) Å, ii: 1-x, 1/2+y, 1/2-z], where Cg1, Cg2 and Cg3 are the centroids of the C6/C7/C8/C9/O1/C1, C1–C6 and C11–C16 rings, respectively). Overall, a two-dimensional architecture is observed in the bc plane.
Coumarin 3-carboxylic acid (1.0 mmol), 4-bromophenol (1.0 mmol) and a catalytic amount of N,N-dimethylaminopyrimidine (DMAP) were dissolved in anhydrous CH2Cl2. To this solution, a solution of dicyclohexylcarbodimide (DCC) in dried CH2Cl2 was added and stirred. After 24 h of stirring, dicyclohexylurea was filtered off and the solution was concentrated. The solid residue obtained was purified by column chromatography on silica gel using CHCl3 as the eluent. Single crystals suitable for X-ray studies were grown by slow evaporation technique at room temperature using ethanol as the solvent.
Hetero cyclic compounds of 2-oxo-2H-chromenes display wide range of biological activities such as anti-HIV (Kostova, et al., 2006), anti-cancer (Abdel-Aziz et al.,2013), etc. They also play a significant role as chemical sensors, fluorescent probes and laser dyes (Chandrasekharan et al., 2002). In continuation of our work on 2-oxo-2H-chromene derivatives (Sreenivasa et al., 2013; Palakshamurthy, Sreenivasa et al., 2013; Palakshamurthy, Devarajegowda et al., 2013; Devarajegowda, et al.,2013), in the present work we report the synthesis and crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate (I), an intermediate compound obtained during synthesis of coumarin–based Liquid Crystals (LCs).
The dihedral angle between the coumarin ring and the bromobenzene ring in (I) is 25.85 (10)°. Compared to this, the dihedral angle is 22.95 (11)° in 4'-cyanobiphenyl-4-yl-7-diethylamino-2-oxo-2H-chromene-3-carboxylate (II) (Sreenivasa et al., 2013), 62.97 (2)° in 4-(decyloxy)phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (III) (Palakshamurthy, Sreenivasa et al., 2013), 21.00 (1)° in 4-(octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate (IV) (Palakshamurthy, Devarajegowda et al., 2013) and 54.46 (17)° in 4-[4-(heptyloxy)benzoyloxy] phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (V) (Devarajegowda, et al., 2013). Further, in (I), the torsions C9—C8—C10—O3, O3—C10—O4—C11 and C12—C11—O4—C10 have values 27.6 (4), 6.3 (3) and 124.6 (2)°, respectively.
In the crystal structure, the molecules are connected along [001] via C12—H12···O3 interactions forming C(6) chains (Fig 2., Table 2). Further, neighbouring C(6) chains are interlocked via π···π interactions (Fig. 3), namely, Cg1··· Cg3i [3.7254 (15) Å, i: 1-x, 1/2+y, 1/2-z] and Cg2··· Cg3i,ii [3.7303 (16) and 3.7716 (16) Å, ii: 1-x, 1/2+y, 1/2-z], where Cg1, Cg2 and Cg3 are the centroids of the C6/C7/C8/C9/O1/C1, C1–C6 and C11–C16 rings, respectively). Overall, a two-dimensional architecture is observed in the bc plane.
For related structures, see: Sreenivasa et al. (2013); Palakshamurthy, Sreenivasa et al. (2013); Palakshamurthy, Devarajegowda et al. (2013); Devarajegowda et al. (2013). For the biological activity and other applications of 2-oxo-2H-chromene derivatives, see: Abdel-Aziz et al. (2013); Kostova (2006); Chandrasekharan & Kelly (2002).
Coumarin 3-carboxylic acid (1.0 mmol), 4-bromophenol (1.0 mmol) and a catalytic amount of N,N-dimethylaminopyrimidine (DMAP) were dissolved in anhydrous CH2Cl2. To this solution, a solution of dicyclohexylcarbodimide (DCC) in dried CH2Cl2 was added and stirred. After 24 h of stirring, dicyclohexylurea was filtered off and the solution was concentrated. The solid residue obtained was purified by column chromatography on silica gel using CHCl3 as the eluent. Single crystals suitable for X-ray studies were grown by slow evaporation technique at room temperature using ethanol as the solvent.
The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93Å, and with 1.2Ueq(C). Owing to poor agreement, several reflections, i.e. (0 2 5), (-1 0 2), (-2 0 8), (7 0 0) and (-7 2 5), were omitted from the final cycles of refinement.
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C16H9BrO4 | Prism |
Mr = 345.14 | Dx = 1.678 Mg m−3 |
Monoclinic, P21/c | Melting point: 523 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.0782 (10) Å | Cell parameters from 2395 reflections |
b = 7.2618 (4) Å | θ = 2.8–25.0° |
c = 12.7396 (8) Å | µ = 3.02 mm−1 |
β = 113.311 (4)° | T = 296 K |
V = 1366.01 (15) Å3 | Prism, colourless |
Z = 4 | 0.24 × 0.18 × 0.16 mm |
F(000) = 688 |
Bruker APEXII CCD diffractometer | 2395 independent reflections |
Radiation source: fine-focus sealed tube | 1831 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 2.01 pixels mm-1 | θmax = 25.0°, θmin = 2.8° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −8→8 |
Tmin = 0.526, Tmax = 0.617 | l = −15→15 |
20483 measured reflections |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0319P)2 + 0.8274P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
2395 reflections | Δρmax = 0.45 e Å−3 |
191 parameters | Δρmin = −0.54 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.0062 (6) |
Primary atom site location: structure-invariant direct methods |
C16H9BrO4 | V = 1366.01 (15) Å3 |
Mr = 345.14 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.0782 (10) Å | µ = 3.02 mm−1 |
b = 7.2618 (4) Å | T = 296 K |
c = 12.7396 (8) Å | 0.24 × 0.18 × 0.16 mm |
β = 113.311 (4)° |
Bruker APEXII CCD diffractometer | 2395 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 1831 reflections with I > 2σ(I) |
Tmin = 0.526, Tmax = 0.617 | Rint = 0.037 |
20483 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.45 e Å−3 |
2395 reflections | Δρmin = −0.54 e Å−3 |
191 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.94359 (2) | 0.14526 (6) | 0.64830 (3) | 0.0907 (2) | |
O1 | 0.31144 (12) | 0.1686 (2) | −0.06316 (14) | 0.0517 (5) | |
O2 | 0.44603 (13) | 0.1964 (3) | −0.06745 (15) | 0.0612 (5) | |
O3 | 0.58965 (12) | 0.2657 (3) | 0.15291 (14) | 0.0556 (5) | |
O4 | 0.56890 (11) | 0.0734 (2) | 0.27929 (13) | 0.0428 (4) | |
C1 | 0.25543 (17) | 0.1424 (3) | −0.0061 (2) | 0.0460 (6) | |
C2 | 0.1631 (2) | 0.1504 (4) | −0.0694 (3) | 0.0613 (8) | |
H2 | 0.1403 | 0.1720 | −0.1477 | 0.074* | |
C3 | 0.1059 (2) | 0.1257 (4) | −0.0142 (3) | 0.0709 (9) | |
H3 | 0.0436 | 0.1322 | −0.0558 | 0.085* | |
C4 | 0.1389 (2) | 0.0915 (4) | 0.1017 (3) | 0.0673 (9) | |
H4 | 0.0990 | 0.0734 | 0.1372 | 0.081* | |
C5 | 0.23074 (18) | 0.0840 (4) | 0.1648 (3) | 0.0547 (7) | |
H5 | 0.2530 | 0.0613 | 0.2429 | 0.066* | |
C6 | 0.29078 (17) | 0.1108 (3) | 0.1108 (2) | 0.0413 (6) | |
C7 | 0.38706 (16) | 0.1145 (3) | 0.1709 (2) | 0.0394 (6) | |
H7 | 0.4122 | 0.0939 | 0.2493 | 0.047* | |
C8 | 0.44200 (16) | 0.1472 (3) | 0.11609 (19) | 0.0364 (6) | |
C9 | 0.40485 (18) | 0.1736 (3) | −0.0079 (2) | 0.0440 (6) | |
C10 | 0.54071 (17) | 0.1702 (3) | 0.18007 (19) | 0.0385 (6) | |
C11 | 0.65769 (16) | 0.0988 (3) | 0.36007 (19) | 0.0370 (5) | |
C12 | 0.66608 (17) | 0.1487 (3) | 0.4677 (2) | 0.0433 (6) | |
H12 | 0.6149 | 0.1711 | 0.4827 | 0.052* | |
C13 | 0.75178 (19) | 0.1654 (4) | 0.5536 (2) | 0.0517 (7) | |
H13 | 0.7590 | 0.2000 | 0.6270 | 0.062* | |
C14 | 0.82608 (18) | 0.1301 (4) | 0.5288 (2) | 0.0499 (7) | |
C15 | 0.81735 (18) | 0.0805 (4) | 0.4214 (2) | 0.0538 (7) | |
H15 | 0.8686 | 0.0581 | 0.4065 | 0.065* | |
C16 | 0.73210 (17) | 0.0637 (4) | 0.3352 (2) | 0.0452 (6) | |
H16 | 0.7251 | 0.0293 | 0.2619 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0491 (2) | 0.1081 (3) | 0.0795 (3) | −0.01632 (19) | −0.01221 (17) | 0.0173 (2) |
O1 | 0.0460 (11) | 0.0681 (12) | 0.0343 (9) | 0.0056 (9) | 0.0087 (8) | −0.0015 (8) |
O2 | 0.0622 (13) | 0.0888 (15) | 0.0368 (10) | 0.0067 (11) | 0.0240 (10) | 0.0059 (10) |
O3 | 0.0497 (11) | 0.0724 (13) | 0.0443 (10) | −0.0097 (10) | 0.0181 (9) | 0.0127 (9) |
O4 | 0.0364 (9) | 0.0547 (10) | 0.0336 (9) | −0.0038 (8) | 0.0100 (7) | 0.0081 (8) |
C1 | 0.0401 (15) | 0.0421 (15) | 0.0489 (15) | 0.0008 (11) | 0.0102 (13) | −0.0059 (12) |
C2 | 0.0473 (18) | 0.0615 (19) | 0.0576 (18) | 0.0004 (14) | 0.0020 (15) | −0.0034 (14) |
C3 | 0.0383 (17) | 0.064 (2) | 0.096 (3) | −0.0063 (14) | 0.0115 (18) | −0.0058 (18) |
C4 | 0.0465 (18) | 0.064 (2) | 0.094 (3) | −0.0078 (15) | 0.0305 (18) | −0.0008 (18) |
C5 | 0.0470 (17) | 0.0564 (17) | 0.0636 (17) | −0.0055 (14) | 0.0250 (15) | 0.0011 (14) |
C6 | 0.0403 (14) | 0.0363 (14) | 0.0455 (14) | 0.0000 (11) | 0.0150 (12) | −0.0028 (11) |
C7 | 0.0421 (14) | 0.0375 (13) | 0.0367 (13) | 0.0018 (11) | 0.0135 (11) | −0.0006 (10) |
C8 | 0.0421 (14) | 0.0352 (13) | 0.0316 (12) | 0.0027 (10) | 0.0144 (11) | −0.0010 (10) |
C9 | 0.0464 (15) | 0.0485 (15) | 0.0335 (13) | 0.0059 (12) | 0.0121 (12) | −0.0013 (11) |
C10 | 0.0433 (14) | 0.0409 (14) | 0.0336 (13) | 0.0007 (11) | 0.0178 (11) | −0.0006 (10) |
C11 | 0.0333 (13) | 0.0405 (13) | 0.0354 (12) | −0.0006 (11) | 0.0117 (10) | 0.0040 (10) |
C12 | 0.0401 (15) | 0.0506 (15) | 0.0407 (14) | 0.0037 (12) | 0.0177 (12) | 0.0031 (11) |
C13 | 0.0576 (18) | 0.0535 (16) | 0.0374 (14) | −0.0025 (13) | 0.0120 (13) | 0.0006 (12) |
C14 | 0.0381 (15) | 0.0502 (16) | 0.0487 (16) | −0.0054 (12) | 0.0036 (12) | 0.0084 (12) |
C15 | 0.0375 (15) | 0.0610 (17) | 0.0630 (18) | 0.0030 (13) | 0.0200 (14) | 0.0106 (14) |
C16 | 0.0445 (15) | 0.0535 (16) | 0.0399 (13) | 0.0011 (12) | 0.0192 (12) | 0.0023 (12) |
Br1—C14 | 1.903 (3) | C5—H5 | 0.9300 |
O1—C1 | 1.376 (3) | C6—C7 | 1.430 (3) |
O1—C9 | 1.384 (3) | C7—C8 | 1.346 (3) |
O2—C9 | 1.200 (3) | C7—H7 | 0.9300 |
O3—C10 | 1.198 (3) | C8—C9 | 1.463 (3) |
O4—C10 | 1.358 (3) | C8—C10 | 1.479 (3) |
O4—C11 | 1.403 (3) | C11—C12 | 1.372 (3) |
C1—C2 | 1.382 (4) | C11—C16 | 1.377 (3) |
C1—C6 | 1.387 (4) | C12—C13 | 1.385 (4) |
C2—C3 | 1.373 (5) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.375 (4) |
C3—C4 | 1.380 (5) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.368 (4) |
C4—C5 | 1.374 (4) | C15—C16 | 1.381 (4) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C6 | 1.402 (4) | C16—H16 | 0.9300 |
C1—O1—C9 | 122.67 (19) | C9—C8—C10 | 118.1 (2) |
C10—O4—C11 | 118.88 (18) | O2—C9—O1 | 116.2 (2) |
O1—C1—C2 | 117.5 (2) | O2—C9—C8 | 127.5 (2) |
O1—C1—C6 | 121.0 (2) | O1—C9—C8 | 116.3 (2) |
C2—C1—C6 | 121.5 (3) | O3—C10—O4 | 123.6 (2) |
C3—C2—C1 | 118.6 (3) | O3—C10—C8 | 126.2 (2) |
C3—C2—H2 | 120.7 | O4—C10—C8 | 110.2 (2) |
C1—C2—H2 | 120.7 | C12—C11—C16 | 121.9 (2) |
C2—C3—C4 | 121.3 (3) | C12—C11—O4 | 115.9 (2) |
C2—C3—H3 | 119.4 | C16—C11—O4 | 122.1 (2) |
C4—C3—H3 | 119.4 | C11—C12—C13 | 119.1 (2) |
C5—C4—C3 | 120.2 (3) | C11—C12—H12 | 120.4 |
C5—C4—H4 | 119.9 | C13—C12—H12 | 120.4 |
C3—C4—H4 | 119.9 | C14—C13—C12 | 119.0 (2) |
C4—C5—C6 | 119.8 (3) | C14—C13—H13 | 120.5 |
C4—C5—H5 | 120.1 | C12—C13—H13 | 120.5 |
C6—C5—H5 | 120.1 | C15—C14—C13 | 121.6 (2) |
C1—C6—C5 | 118.7 (2) | C15—C14—Br1 | 119.5 (2) |
C1—C6—C7 | 117.9 (2) | C13—C14—Br1 | 118.9 (2) |
C5—C6—C7 | 123.3 (2) | C14—C15—C16 | 119.7 (2) |
C8—C7—C6 | 121.3 (2) | C14—C15—H15 | 120.2 |
C8—C7—H7 | 119.4 | C16—C15—H15 | 120.2 |
C6—C7—H7 | 119.4 | C11—C16—C15 | 118.7 (2) |
C7—C8—C9 | 120.8 (2) | C11—C16—H16 | 120.7 |
C7—C8—C10 | 121.0 (2) | C15—C16—H16 | 120.7 |
C9—O1—C1—C2 | 176.4 (2) | C7—C8—C9—O1 | 2.0 (3) |
C9—O1—C1—C6 | −3.1 (4) | C10—C8—C9—O1 | −173.9 (2) |
O1—C1—C2—C3 | −179.7 (2) | C11—O4—C10—O3 | 6.3 (3) |
C6—C1—C2—C3 | −0.2 (4) | C11—O4—C10—C8 | −170.71 (19) |
C1—C2—C3—C4 | −0.7 (4) | C7—C8—C10—O3 | −148.3 (3) |
C2—C3—C4—C5 | 0.9 (5) | C9—C8—C10—O3 | 27.6 (4) |
C3—C4—C5—C6 | −0.2 (4) | C7—C8—C10—O4 | 28.7 (3) |
O1—C1—C6—C5 | −179.7 (2) | C9—C8—C10—O4 | −155.5 (2) |
C2—C1—C6—C5 | 0.9 (4) | C10—O4—C11—C12 | 124.6 (2) |
O1—C1—C6—C7 | 2.8 (3) | C10—O4—C11—C16 | −59.7 (3) |
C2—C1—C6—C7 | −176.7 (2) | C16—C11—C12—C13 | 0.4 (4) |
C4—C5—C6—C1 | −0.7 (4) | O4—C11—C12—C13 | 176.2 (2) |
C4—C5—C6—C7 | 176.7 (3) | C11—C12—C13—C14 | −0.5 (4) |
C1—C6—C7—C8 | −0.1 (3) | C12—C13—C14—C15 | 0.5 (4) |
C5—C6—C7—C8 | −177.6 (2) | C12—C13—C14—Br1 | −177.94 (19) |
C6—C7—C8—C9 | −2.2 (3) | C13—C14—C15—C16 | −0.5 (4) |
C6—C7—C8—C10 | 173.5 (2) | Br1—C14—C15—C16 | 178.0 (2) |
C1—O1—C9—O2 | 179.7 (2) | C12—C11—C16—C15 | −0.3 (4) |
C1—O1—C9—C8 | 0.7 (3) | O4—C11—C16—C15 | −175.9 (2) |
C7—C8—C9—O2 | −176.9 (3) | C14—C15—C16—C11 | 0.4 (4) |
C10—C8—C9—O2 | 7.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O3i | 0.93 | 2.40 | 3.124 (3) | 134 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O3i | 0.93 | 2.40 | 3.124 (3) | 134 |
Symmetry code: (i) x, −y+1/2, z+1/2. |