organic compounds
E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid
of (aInternational Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University. 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan, and bDepartment of Applied Chemistry, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
*Correspondence e-mail: mwata@i2cner.kyushu-u.ac.jp
In the title compound, C21H14N2O2S, a donor–acceptor type of benzo[b]phenothiazine (bpz) derivative, the thiazine ring adopts a boat conformation and the bond-angle sum at the N atom is 360.0°. The dihedral angle between the benzene ring and the naphthelene ring system fused to the thiazine ring is 32.76 (5)°. In the crystal, carboxylic-acid inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R22(8) loops. Aromatic π–π stacking [shortest centroid–centroid separaton = 3.5242 (13)Å] consolidates the structure and very weak C—H⋯O and C—H⋯N interactions also occur.
Keywords: crystal structure; benzo[b]phenothiazine derivative; inversion dimers; hydrogen bonding; π–π stacking.
CCDC reference: 1018980
1. Related literature
For related structures, see: Bell et al. (1968), van de Waal & Feil (1977), Sun et al. (2004); Harrison et al. (2007). For applications of the title compound in dye-sensitized solar cells, see: Watanabe et al. (2014).
2. Experimental
2.1. Crystal data
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2.2. Data collection
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2.3. Refinement
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009) and POV-RAY (Persistence of Vision Team, 2004).
Supporting information
CCDC reference: 1018980
10.1107/S1600536814018388/hb7264sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018388/hb7264Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018388/hb7264Isup3.cml
Phenothiazine, C12H9NS showed stable redox properties. This crystal struture have been reported for the neutral state (Bell et al., 1968, and van de Wall & Feli, 1977), and for the C12H9NS+
state (Sun et al., 2004), and phenothiazine-picric acid (1/1) (Harrison et al., 2007).As part of our studies for understanding the donor-acceptor interaction type dye molecule for dye-sensitized solar cell (Watanabe et al., 2014), we now report the title compound. In the title compound, C21H14N2O2S, consists a 12-methyl-12H-benzo[b]phenothiazine as a donor moiety, which has a (E)-2-cyanobut-2-enoic acid moiety as acceptor at C-11 position of 12-methyl-12H-benzo[b]phenothiazine.
Dark-red crystals were obtained from 0.013 g of title compound in tetrahydrofuran (10 ml) solution by slow diffusion.
The C21H14N2O2S of 12-methyl-12H-benzo[b]phenothiazine moiety takes pyramidal structure, in which benzene and naphthalene had 147.2°, while the olefin bond at the cyanoacrylic moiety existed 123.8° from the naphthalene plane (Figure 1). The title compounds showed an intermolecular hydrogen bonding at O1—H14 - O2' (1.520 Å) in the two molecule structure of carboxylic acid moiety (Figure 2). Furthermore, title compound have π-π stacking orientation along with a axis, where the two-naphthalene moieties oriented the parallel structures, which has a transannular distance at 3.273 Å (Figure 3).
The chloroform solution (10 ml) of title compound (0.013 g) was standing under ambient condition until the desired single crystal was produced.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009) and POV-RAY (Persistence of Vision Team, 2004).Fig. 1. The molecular structure of C21H14N2O2S with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Intermolecular hydrogen bonding O1—H14—O2' (1.520 Å) in the two molecule structure of carboxylic acid moiety. | |
Fig. 3. Packing diagram of C21H14N2O2S. |
C21H14N2O2S | F(000) = 372 |
Mr = 358.40 | Dx = 1.402 Mg m−3 |
Triclinic, P1 | Melting point: 351 K |
a = 6.7915 (17) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 9.196 (3) Å | Cell parameters from 14164 reflections |
c = 13.941 (3) Å | θ = 3.0–27.5° |
α = 95.831 (13)° | µ = 0.21 mm−1 |
β = 101.214 (10)° | T = 123 K |
γ = 90.850 (15)° | Block, dark red |
V = 849.1 (4) Å3 | 0.40 × 0.40 × 0.15 mm |
Z = 2 |
Rigaku R-AXIS RAPID CCD diffractometer | Rint = 0.020 |
ω/2θ scans | θmax = 27.5°, θmin = 3.0° |
14164 measured reflections | h = −8→8 |
3877 independent reflections | k = −11→11 |
3663 reflections with I > 2σ(I) | l = −18→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2744P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3877 reflections | Δρmax = 0.29 e Å−3 |
290 parameters | Δρmin = −0.40 e Å−3 |
C21H14N2O2S | γ = 90.850 (15)° |
Mr = 358.40 | V = 849.1 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7915 (17) Å | Mo Kα radiation |
b = 9.196 (3) Å | µ = 0.21 mm−1 |
c = 13.941 (3) Å | T = 123 K |
α = 95.831 (13)° | 0.40 × 0.40 × 0.15 mm |
β = 101.214 (10)° |
Rigaku R-AXIS RAPID CCD diffractometer | 3663 reflections with I > 2σ(I) |
14164 measured reflections | Rint = 0.020 |
3877 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.29 e Å−3 |
3877 reflections | Δρmin = −0.40 e Å−3 |
290 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 | ||
H2 | 0.953 (3) | −0.333 (2) | 0.4654 (13) | 0.041 (5)* | |
H3 | 0.968 (3) | −0.526 (2) | 0.3462 (15) | 0.056 (6)* | |
C1 | 0.71497 (19) | −0.23569 (15) | 0.38906 (10) | 0.0297 (3) | |
H10 | 0.213 (2) | −0.0357 (18) | 0.3396 (12) | 0.029 (4)* | |
C2 | 0.8586 (2) | −0.34194 (17) | 0.40418 (12) | 0.0371 (3) | |
C3 | 0.8644 (2) | −0.45592 (16) | 0.33152 (13) | 0.0402 (3) | |
C4 | 0.7256 (2) | −0.46500 (15) | 0.24404 (12) | 0.0353 (3) | |
C5 | 0.12589 (17) | 0.17296 (15) | −0.11405 (9) | 0.0274 (3) | |
H5 | 0.290 (2) | −0.2245 (18) | −0.0436 (12) | 0.033 (4)* | |
H6 | 0.163 (2) | −0.0447 (18) | −0.1546 (12) | 0.031 (4)* | |
H9 | 0.238 (2) | 0.3227 (18) | 0.1163 (12) | 0.031 (4)* | |
C6 | 0.22142 (17) | 0.24648 (13) | 0.06076 (9) | 0.0223 (2) | |
C7 | 0.34176 (15) | 0.06021 (12) | 0.17662 (8) | 0.0173 (2) | |
S1 | 0.39308 (5) | −0.37579 (3) | 0.12102 (2) | 0.02878 (11) | |
O1 | 0.65112 (12) | 0.36226 (9) | 0.47776 (6) | 0.02296 (18) | |
H7 | 0.075 (3) | 0.1979 (19) | −0.1817 (13) | 0.038 (4)* | |
H1 | 0.714 (2) | −0.1535 (19) | 0.4397 (12) | 0.029 (4)* | |
H8 | 0.124 (3) | 0.386 (2) | −0.0451 (13) | 0.040 (4)* | |
C8 | 0.24793 (16) | −0.00669 (13) | −0.00306 (8) | 0.0202 (2) | |
H4 | 0.725 (3) | −0.541 (2) | 0.1909 (13) | 0.041 (5)* | |
C9 | 0.26789 (15) | 0.10113 (12) | 0.07897 (8) | 0.0181 (2) | |
O2 | 0.35247 (13) | 0.41863 (10) | 0.39083 (6) | 0.0275 (2) | |
H14 | 0.353 (3) | 0.507 (2) | 0.4467 (13) | 0.041* | |
N1 | 0.42827 (14) | −0.13630 (10) | 0.28349 (7) | 0.0208 (2) | |
C10 | 0.38246 (15) | −0.08478 (12) | 0.19057 (8) | 0.0177 (2) | |
H13 | 0.246 (2) | 0.2398 (16) | 0.2575 (11) | 0.023 (3)* | |
C11 | 0.35977 (16) | 0.17829 (12) | 0.25662 (8) | 0.0186 (2) | |
C12 | 0.50856 (16) | 0.34153 (12) | 0.40510 (8) | 0.0185 (2) | |
N2 | 0.86564 (16) | 0.10083 (13) | 0.34623 (9) | 0.0336 (3) | |
H11 | 0.312 (2) | −0.1618 (18) | 0.3995 (12) | 0.031 (4)* | |
H12 | 0.420 (3) | −0.003 (2) | 0.4129 (13) | 0.041 (5)* | |
C13 | 0.30285 (16) | −0.15078 (13) | 0.01314 (8) | 0.0219 (2) | |
C14 | 0.36473 (16) | −0.18954 (12) | 0.10592 (8) | 0.0201 (2) | |
C15 | 0.17442 (17) | 0.03230 (15) | −0.09906 (8) | 0.0250 (2) | |
C16 | 0.15205 (18) | 0.28132 (14) | −0.03332 (9) | 0.0266 (3) | |
C17 | 0.57900 (18) | −0.36047 (13) | 0.22895 (10) | 0.0262 (2) | |
C18 | 0.57427 (17) | −0.24412 (12) | 0.30077 (9) | 0.0231 (2) | |
C19 | 0.33548 (19) | −0.08052 (14) | 0.36491 (9) | 0.0248 (2) | |
C20 | 0.51890 (16) | 0.21732 (12) | 0.32950 (8) | 0.0186 (2) | |
C21 | 0.70959 (17) | 0.14883 (13) | 0.33855 (8) | 0.0222 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0244 (6) | 0.0300 (6) | 0.0354 (7) | 0.0032 (5) | 0.0037 (5) | 0.0107 (5) |
C2 | 0.0239 (6) | 0.0388 (7) | 0.0513 (8) | 0.0065 (5) | 0.0052 (6) | 0.0218 (6) |
C3 | 0.0290 (6) | 0.0339 (7) | 0.0655 (10) | 0.0136 (5) | 0.0183 (6) | 0.0231 (7) |
C4 | 0.0344 (7) | 0.0229 (6) | 0.0559 (9) | 0.0083 (5) | 0.0227 (6) | 0.0106 (6) |
C5 | 0.0187 (5) | 0.0433 (7) | 0.0200 (5) | −0.0067 (5) | 0.0017 (4) | 0.0078 (5) |
C6 | 0.0189 (5) | 0.0240 (6) | 0.0231 (5) | −0.0022 (4) | 0.0023 (4) | 0.0017 (4) |
C7 | 0.0140 (4) | 0.0198 (5) | 0.0168 (5) | −0.0007 (4) | 0.0021 (4) | −0.0026 (4) |
S1 | 0.03269 (18) | 0.01645 (16) | 0.03660 (19) | −0.00299 (11) | 0.00977 (13) | −0.00517 (11) |
O1 | 0.0245 (4) | 0.0230 (4) | 0.0180 (4) | 0.0017 (3) | −0.0007 (3) | −0.0045 (3) |
C8 | 0.0143 (4) | 0.0278 (6) | 0.0176 (5) | −0.0054 (4) | 0.0043 (4) | −0.0026 (4) |
C9 | 0.0130 (4) | 0.0223 (5) | 0.0177 (5) | −0.0028 (4) | 0.0019 (4) | −0.0009 (4) |
O2 | 0.0262 (4) | 0.0258 (4) | 0.0262 (4) | 0.0094 (3) | −0.0004 (3) | −0.0080 (3) |
N1 | 0.0208 (4) | 0.0211 (5) | 0.0207 (4) | 0.0053 (4) | 0.0046 (4) | 0.0015 (3) |
C10 | 0.0137 (4) | 0.0198 (5) | 0.0186 (5) | −0.0008 (4) | 0.0034 (4) | −0.0020 (4) |
C11 | 0.0195 (5) | 0.0178 (5) | 0.0179 (5) | 0.0024 (4) | 0.0034 (4) | −0.0003 (4) |
C12 | 0.0197 (5) | 0.0177 (5) | 0.0170 (5) | 0.0013 (4) | 0.0028 (4) | −0.0012 (4) |
N2 | 0.0236 (5) | 0.0391 (6) | 0.0338 (6) | 0.0074 (4) | 0.0017 (4) | −0.0098 (5) |
C13 | 0.0183 (5) | 0.0251 (6) | 0.0210 (5) | −0.0056 (4) | 0.0065 (4) | −0.0083 (4) |
C14 | 0.0174 (5) | 0.0178 (5) | 0.0247 (5) | −0.0024 (4) | 0.0065 (4) | −0.0042 (4) |
C15 | 0.0176 (5) | 0.0392 (7) | 0.0171 (5) | −0.0080 (4) | 0.0042 (4) | −0.0018 (5) |
C16 | 0.0204 (5) | 0.0320 (6) | 0.0276 (6) | −0.0026 (4) | 0.0024 (4) | 0.0089 (5) |
C17 | 0.0241 (5) | 0.0197 (5) | 0.0381 (6) | 0.0017 (4) | 0.0131 (5) | 0.0055 (5) |
C18 | 0.0191 (5) | 0.0209 (5) | 0.0312 (6) | 0.0027 (4) | 0.0077 (4) | 0.0066 (4) |
C19 | 0.0270 (6) | 0.0275 (6) | 0.0218 (5) | 0.0055 (5) | 0.0086 (4) | 0.0035 (4) |
C20 | 0.0197 (5) | 0.0177 (5) | 0.0176 (5) | 0.0020 (4) | 0.0034 (4) | −0.0026 (4) |
C21 | 0.0218 (5) | 0.0226 (5) | 0.0195 (5) | 0.0005 (4) | 0.0018 (4) | −0.0064 (4) |
C1—C2 | 1.3933 (18) | C8—C15 | 1.4185 (16) |
C1—C18 | 1.3982 (18) | C8—C9 | 1.4192 (15) |
C1—H1 | 0.982 (17) | O2—C12 | 1.2786 (14) |
C2—C3 | 1.388 (2) | O2—H14 | 1.063 (18) |
C2—H2 | 0.959 (18) | N1—C10 | 1.4042 (14) |
C3—C4 | 1.383 (2) | N1—C18 | 1.4174 (14) |
C3—H3 | 0.97 (2) | N1—C19 | 1.4553 (14) |
C4—C17 | 1.3956 (17) | C10—C14 | 1.4301 (15) |
C4—H4 | 0.963 (19) | C11—C20 | 1.3478 (15) |
C5—C15 | 1.366 (2) | C11—H13 | 0.964 (15) |
C5—C16 | 1.4072 (19) | C12—C20 | 1.4855 (15) |
C5—H7 | 0.990 (17) | N2—C21 | 1.1440 (16) |
C6—C16 | 1.3764 (17) | C13—C14 | 1.3650 (17) |
C6—C9 | 1.4145 (16) | C13—H5 | 0.978 (17) |
C6—H9 | 0.978 (17) | C15—H6 | 0.985 (17) |
C7—C10 | 1.3908 (16) | C16—H8 | 1.006 (18) |
C7—C9 | 1.4458 (15) | C17—C18 | 1.3942 (18) |
C7—C11 | 1.4611 (15) | C19—H10 | 0.958 (16) |
S1—C14 | 1.7556 (13) | C19—H11 | 0.957 (17) |
S1—C17 | 1.7581 (14) | C19—H12 | 1.013 (19) |
O1—C12 | 1.2544 (14) | C20—C21 | 1.4376 (15) |
C8—C13 | 1.4101 (17) | ||
C2—C1—C18 | 120.09 (13) | C20—C11—C7 | 128.50 (10) |
C2—C1—H1 | 120.2 (9) | C20—C11—H13 | 114.1 (9) |
C18—C1—H1 | 119.7 (9) | C7—C11—H13 | 117.3 (9) |
C3—C2—C1 | 120.34 (14) | O1—C12—O2 | 125.12 (10) |
C3—C2—H2 | 121.5 (11) | O1—C12—C20 | 118.13 (10) |
C1—C2—H2 | 118.2 (11) | O2—C12—C20 | 116.75 (9) |
C4—C3—C2 | 119.87 (12) | C14—C13—C8 | 121.34 (10) |
C4—C3—H3 | 123.7 (12) | C14—C13—H5 | 120.0 (10) |
C2—C3—H3 | 116.5 (12) | C8—C13—H5 | 118.6 (10) |
C3—C4—C17 | 120.17 (14) | C13—C14—C10 | 121.42 (10) |
C3—C4—H4 | 123.1 (11) | C13—C14—S1 | 118.47 (8) |
C17—C4—H4 | 116.8 (11) | C10—C14—S1 | 119.66 (9) |
C15—C5—C16 | 119.59 (11) | C5—C15—C8 | 120.96 (11) |
C15—C5—H7 | 119.6 (10) | C5—C15—H6 | 121.2 (9) |
C16—C5—H7 | 120.8 (10) | C8—C15—H6 | 117.8 (9) |
C16—C6—C9 | 121.02 (11) | C6—C16—C5 | 120.73 (12) |
C16—C6—H9 | 119.9 (9) | C6—C16—H8 | 119.9 (10) |
C9—C6—H9 | 119.1 (9) | C5—C16—H8 | 119.4 (10) |
C10—C7—C9 | 120.36 (9) | C18—C17—C4 | 120.36 (13) |
C10—C7—C11 | 123.92 (10) | C18—C17—S1 | 118.84 (9) |
C9—C7—C11 | 115.66 (10) | C4—C17—S1 | 120.77 (11) |
C14—S1—C17 | 99.34 (6) | C17—C18—C1 | 119.14 (11) |
C13—C8—C15 | 121.48 (10) | C17—C18—N1 | 119.89 (11) |
C13—C8—C9 | 118.85 (10) | C1—C18—N1 | 120.97 (11) |
C15—C8—C9 | 119.67 (11) | N1—C19—H10 | 109.2 (9) |
C6—C9—C8 | 117.97 (10) | N1—C19—H11 | 107.3 (10) |
C6—C9—C7 | 122.69 (10) | H10—C19—H11 | 111.2 (14) |
C8—C9—C7 | 119.29 (10) | N1—C19—H12 | 114.0 (10) |
C12—O2—H14 | 113.7 (10) | H10—C19—H12 | 106.4 (14) |
C10—N1—C18 | 119.48 (9) | H11—C19—H12 | 108.7 (14) |
C10—N1—C19 | 122.62 (9) | C11—C20—C21 | 123.98 (10) |
C18—N1—C19 | 117.88 (9) | C11—C20—C12 | 120.73 (10) |
C7—C10—N1 | 123.61 (9) | C21—C20—C12 | 115.25 (9) |
C7—C10—C14 | 118.54 (10) | N2—C21—C20 | 176.72 (13) |
N1—C10—C14 | 117.73 (10) | ||
C18—C1—C2—C3 | 0.6 (2) | C7—C10—C14—S1 | −174.34 (8) |
C1—C2—C3—C4 | −0.7 (2) | N1—C10—C14—S1 | 1.83 (13) |
C2—C3—C4—C17 | −0.4 (2) | C17—S1—C14—C13 | 152.24 (9) |
C16—C6—C9—C8 | 2.30 (16) | C17—S1—C14—C10 | −35.38 (10) |
C16—C6—C9—C7 | 179.77 (10) | C16—C5—C15—C8 | 0.99 (17) |
C13—C8—C9—C6 | 176.94 (9) | C13—C8—C15—C5 | −178.54 (10) |
C15—C8—C9—C6 | −2.82 (15) | C9—C8—C15—C5 | 1.22 (16) |
C13—C8—C9—C7 | −0.62 (15) | C9—C6—C16—C5 | −0.12 (18) |
C15—C8—C9—C7 | 179.61 (9) | C15—C5—C16—C6 | −1.56 (18) |
C10—C7—C9—C6 | 179.09 (9) | C3—C4—C17—C18 | 1.62 (19) |
C11—C7—C9—C6 | 1.88 (15) | C3—C4—C17—S1 | −176.53 (10) |
C10—C7—C9—C8 | −3.47 (15) | C14—S1—C17—C18 | 36.16 (10) |
C11—C7—C9—C8 | 179.32 (9) | C14—S1—C17—C4 | −145.67 (10) |
C9—C7—C10—N1 | −171.10 (9) | C4—C17—C18—C1 | −1.66 (17) |
C11—C7—C10—N1 | 5.86 (16) | S1—C17—C18—C1 | 176.53 (9) |
C9—C7—C10—C14 | 4.83 (15) | C4—C17—C18—N1 | 178.19 (11) |
C11—C7—C10—C14 | −178.20 (9) | S1—C17—C18—N1 | −3.63 (15) |
C18—N1—C10—C7 | −142.33 (11) | C2—C1—C18—C17 | 0.53 (18) |
C19—N1—C10—C7 | 35.94 (16) | C2—C1—C18—N1 | −179.31 (11) |
C18—N1—C10—C14 | 41.71 (14) | C10—N1—C18—C17 | −41.32 (15) |
C19—N1—C10—C14 | −140.02 (11) | C19—N1—C18—C17 | 140.33 (11) |
C10—C7—C11—C20 | 53.51 (17) | C10—N1—C18—C1 | 138.52 (11) |
C9—C7—C11—C20 | −129.39 (12) | C19—N1—C18—C1 | −39.83 (16) |
C15—C8—C13—C14 | −176.93 (10) | C7—C11—C20—C21 | 2.65 (19) |
C9—C8—C13—C14 | 3.31 (16) | C7—C11—C20—C12 | −179.85 (10) |
C8—C13—C14—C10 | −1.94 (16) | O1—C12—C20—C11 | 171.53 (10) |
C8—C13—C14—S1 | 170.30 (8) | O2—C12—C20—C11 | −7.97 (16) |
C7—C10—C14—C13 | −2.19 (15) | O1—C12—C20—C21 | −10.77 (15) |
N1—C10—C14—C13 | 173.98 (10) | O2—C12—C20—C21 | 169.73 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H14···O1i | 1.063 (18) | 1.524 (18) | 2.5856 (13) | 176.8 (16) |
C19—H10···N2ii | 0.958 (16) | 2.699 (16) | 3.5991 (18) | 156.8 (13) |
C19—H11···O1iii | 0.957 (17) | 2.623 (17) | 3.5518 (17) | 163.7 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H14···O1i | 1.063 (18) | 1.524 (18) | 2.5856 (13) | 176.8 (16) |
C19—H10···N2ii | 0.958 (16) | 2.699 (16) | 3.5991 (18) | 156.8 (13) |
C19—H11···O1iii | 0.957 (17) | 2.623 (17) | 3.5518 (17) | 163.7 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y, −z+1. |
Acknowledgements
This work was supported by a Grant-in-Aid for Science Research (YB 26810107) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan, and was performed under the Cooperative Research Program of "Network Joint Research Center for Materials and Devices (IMCE, Kyushu University)". MW thanks the World Premier International Research Center Initiative (WPI), Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), Japan.
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