Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]pheno­thia­zin-11-yl)acrylic acid

Watanabe, M.; Ishihara, T.

doi:10.1107/S1600536814018388

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1026-o1027

doi:10.1107/S1600536814018388

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Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid

Motonori Watanabe ^a ^* and Tatsumi Ishihara ^a,^b

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 31 July 2014; accepted 12 August 2014; online 20 August 2014)

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

C₂₁H₁₄N₂O₂S
M_r = 358.40
Triclinic, $[P \overline 1]$
a = 6.7915 (17) Å
b = 9.196 (3) Å
c = 13.941 (3) Å
α = 95.831 (13)°
β = 101.214 (10)°
γ = 90.850 (15)°
V = 849.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 123 K
0.40 × 0.40 × 0.15 mm

2.2. Data collection

Rigaku R-AXIS RAPID CCD diffractometer
14164 measured reflections
3877 independent reflections
3663 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.06
3877 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: 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

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814018388/hb7264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018388/hb7264Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018388/hb7264Isup3.cml

checkCIF report

Structural commentary top

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+ radical cation 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).

Crystallization top

The chloroform solution (10 ml) of title compound (0.013 g) was standing under ambient condition until the desired single crystal was produced.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All the hydrogen atoms of the compound are fixed geometrically (C—H = 0.95 - 1.01 Å) and allowed to ride on their parent atoms. Structure was refined with unique reflections and with a cut-off sigma = 2.00.

Related literature top

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).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: 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).

Figures top

	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.

(E)-2-Cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid top

Crystal data top

C₂₁H₁₄N₂O₂S	F(000) = 372
M_r = 358.40	D_x = 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

Data collection top

Rigaku R-AXIS RAPID CCD diffractometer	R_int = 0.020
ω/2θ scans	θ_max = 27.5°, θ_min = 3.0°
14164 measured reflections	h = −8→8
3877 independent reflections	k = −11→11
3663 reflections with I > 2σ(I)	l = −18→16

Refinement top

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(F_o²) + (0.0609P)² + 0.2744P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3877 reflections	Δρ_max = 0.29 e Å⁻³
290 parameters	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₁H₁₄N₂O₂S	γ = 90.850 (15)°
M_r = 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)°

Data collection top

Rigaku R-AXIS RAPID CCD diffractometer	3663 reflections with I > 2σ(I)
14164 measured reflections	R_int = 0.020
3877 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.29 e Å⁻³
3877 reflections	Δρ_min = −0.40 e Å⁻³
290 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bell, J. D., Blount, J. F., Briscoe, O. V. & Freeman, H. C. (1968). Chem. Commun. pp. 1656–1657. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Harrison, W. T. A., Ashok, M. A., Yathirajan, H. S. & Narayana Achar, B. (2007). Acta Cryst. E63, o3322. CSD CrossRef IUCr Journals Google Scholar
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn, 51, 218–224. CrossRef Google Scholar
Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Williamstown, Victoria, Australia. http://www.povray.org/ . Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, D., Rosokha, S. V. & Kochi, J. K. (2004). J. Am. Chem. Soc. 126, 1388–1401. Web of Science CSD CrossRef PubMed CAS Google Scholar
Waal, B. W. van de & Feil, D. (1977). Acta Cryst. B33, 314–315. Google Scholar
Wakita, K. (2001). Yadokari-XG. http://www.hat.hi-ho.ne.jp/k-wakita/yadokari . Google Scholar
Watanabe, M., Hagiwara, H., Iribe, A., Ogata, Y., Shiomi, K., Staykov, A., Ida, S., Tanaka, K. & Ishihara, T. (2014). J. Mater. Chem. A, 2, 12952–12961. Web of Science CrossRef CAS Google Scholar

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Volume 70| Part 9| September 2014| Pages o1026-o1027

doi:10.1107/S1600536814018388

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]pheno­thia­zin-11-yl)acrylic acid

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid