Oxomemazine hydro-chloride.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 3-(5,5-dioxo-phen-othia-zin-10-yl)-N,N,2-trimethyl-propanaminium chloride], C(18)H(23)N(2)O(2)S(+)·Cl(-), the dihedral angle between the two outer aromatic rings of the phenothia-zine unit is 30.5 (2)°. In the crystal, the components are linked by N-H⋯Cl and C-H⋯Cl hydrogen bonds and C-H⋯π inter-actions.

Related literature

For background to oxomemazine, see: Amin et al. (2008 ▶); El-Didamony, (2005 ▶). For related structures, see: Harrison et al. (2007 ▶); Jasinski et al. (2011 ▶).

Experimental

Crystal data

C18H23N2O2S+·Cl−

M = 366.90

Triclinic,

a = 7.6364 (7) Å

b = 10.4177 (9) Å

c = 12.4732 (10) Å

α = 103.478 (7)°

β = 90.624 (7)°

γ = 109.852 (8)°

V = 903.21 (15) Å3

Z = 2

Cu Kα radiation

μ = 3.06 mm−1

T = 295 K

0.32 × 0.25 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: refined from ΔF [XABS2 (Parkin et al., 1995 ▶) in WinGX (Farrugia (1999 ▶)]T min = 0.441, T max = 0.528

6466 measured reflections

3598 independent reflections

3120 reflections with I > 2σ(I)

R int = 0.0422

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.229

S = 1.09

3598 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025372/hb5925sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025372/hb5925Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025372/hb5925Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H23N2O2S+·Cl−	Z = 2
Mr = 366.90	F(000) = 388
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.6364 (7) Å	Cell parameters from 3224 reflections
b = 10.4177 (9) Å	θ = 4.7–75.0°
c = 12.4732 (10) Å	µ = 3.06 mm−1
α = 103.478 (7)°	T = 295 K
β = 90.624 (7)°	Prism, colourless
γ = 109.852 (8)°	0.32 × 0.25 × 0.24 mm
V = 903.21 (15) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3598 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3120 reflections with I > 2σ(I)
graphite	Rint = 0.074
Detector resolution: 10.5081 pixels mm-1	θmax = 75.8°, θmin = 4.7°
ω scans	h = −9→9
Absorption correction: part of the refinement model (ΔF) [XABS2 (Parkin et al., 1995) in the WinGX (Farrugia (1999).	k = −12→12
Tmin = 0.441, Tmax = 0.528	l = 0→15
6466 measured reflections

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1168P)2 + 1.2778P] where P = (Fo2 + 2Fc2)/3
3598 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.59166 (14)	0.20629 (10)	0.95014 (7)	0.0449 (3)
O1	0.5426 (5)	0.1883 (4)	1.0580 (2)	0.0663 (10)
O2	0.7225 (4)	0.1441 (3)	0.9009 (3)	0.0587 (10)
N1	0.5526 (5)	0.3244 (3)	0.7585 (3)	0.0434 (9)
N2	0.5857 (5)	0.2792 (4)	0.3894 (3)	0.0448 (10)
C1	0.4037 (5)	0.2045 (4)	0.7654 (3)	0.0401 (10)
C2	0.2542 (6)	0.1382 (4)	0.6801 (3)	0.0492 (11)
C3	0.1031 (6)	0.0237 (5)	0.6921 (4)	0.0552 (14)
C4	0.0937 (6)	−0.0284 (5)	0.7851 (4)	0.0590 (14)
C5	0.2388 (6)	0.0333 (4)	0.8684 (4)	0.0511 (12)
C6	0.3941 (5)	0.1471 (4)	0.8570 (3)	0.0412 (10)
C7	0.6735 (5)	0.3847 (4)	0.9521 (3)	0.0412 (11)
C8	0.7662 (6)	0.4839 (4)	1.0502 (3)	0.0495 (11)
C9	0.8514 (6)	0.6230 (5)	1.0501 (4)	0.0547 (12)
C10	0.8428 (6)	0.6621 (4)	0.9525 (4)	0.0540 (11)
C11	0.7472 (6)	0.5662 (4)	0.8560 (4)	0.0503 (12)
C12	0.6580 (5)	0.4229 (4)	0.8529 (3)	0.0400 (10)
C13	0.5914 (6)	0.3516 (4)	0.6489 (3)	0.0443 (11)
C14	0.6707 (6)	0.2476 (5)	0.5775 (3)	0.0494 (12)
C15	0.8375 (9)	0.2381 (8)	0.6378 (5)	0.084 (2)
C16	0.7363 (6)	0.2971 (5)	0.4743 (3)	0.0507 (14)
C17	0.4856 (8)	0.1292 (5)	0.3288 (5)	0.0709 (17)
C18	0.6669 (8)	0.3653 (6)	0.3094 (4)	0.0664 (16)
Cl1	0.22428 (14)	0.32837 (11)	0.44260 (9)	0.0524 (3)
H2A	0.25720	0.17110	0.61670	0.0590*
H2B	0.50060	0.31300	0.42450	0.0540*
H3A	0.00520	−0.01930	0.63590	0.0660*
H4A	−0.00980	−0.10460	0.79140	0.0710*
H5A	0.23360	−0.00030	0.93150	0.0610*
H8A	0.77010	0.45550	1.11530	0.0600*
H9A	0.91380	0.68960	1.11470	0.0650*
H10A	0.90310	0.75580	0.95170	0.0650*
H11A	0.74180	0.59690	0.79220	0.0600*
H13A	0.68010	0.44670	0.65870	0.0530*
H13B	0.47660	0.34550	0.61050	0.0530*
H14A	0.57280	0.15410	0.55540	0.0590*
H15A	0.79770	0.19790	0.69920	0.1250*
H15B	0.92950	0.33080	0.66460	0.1250*
H15C	0.89070	0.17960	0.58800	0.1250*
H16A	0.81350	0.39620	0.49720	0.0610*
H16B	0.81480	0.24610	0.44000	0.0610*
H17A	0.41330	0.07910	0.37840	0.1060*
H17B	0.57500	0.08670	0.30100	0.1060*
H17C	0.40390	0.12520	0.26810	0.1060*
H18A	0.72400	0.46260	0.34880	0.0990*
H18B	0.56930	0.35570	0.25570	0.0990*
H18C	0.75940	0.33290	0.27250	0.0990*

	U11	U22	U33	U12	U13	U23
S1	0.0587 (6)	0.0433 (5)	0.0309 (5)	0.0145 (4)	−0.0028 (4)	0.0112 (3)
O1	0.095 (2)	0.0633 (19)	0.0316 (15)	0.0125 (17)	−0.0023 (15)	0.0187 (13)
O2	0.0562 (17)	0.0536 (17)	0.069 (2)	0.0230 (14)	−0.0042 (15)	0.0155 (15)
N1	0.0551 (18)	0.0425 (16)	0.0297 (15)	0.0128 (14)	0.0014 (13)	0.0101 (12)
N2	0.0564 (18)	0.0517 (18)	0.0292 (15)	0.0247 (15)	0.0070 (13)	0.0070 (12)
C1	0.0470 (19)	0.0416 (18)	0.0321 (17)	0.0179 (15)	0.0046 (14)	0.0063 (14)
C2	0.058 (2)	0.053 (2)	0.0380 (19)	0.0230 (18)	−0.0036 (17)	0.0090 (16)
C3	0.048 (2)	0.051 (2)	0.058 (3)	0.0115 (17)	−0.0092 (18)	0.0070 (19)
C4	0.052 (2)	0.050 (2)	0.068 (3)	0.0080 (18)	0.001 (2)	0.017 (2)
C5	0.056 (2)	0.047 (2)	0.048 (2)	0.0138 (17)	0.0061 (18)	0.0143 (17)
C6	0.0487 (19)	0.0388 (17)	0.0350 (18)	0.0151 (15)	0.0026 (14)	0.0075 (14)
C7	0.052 (2)	0.0384 (18)	0.0298 (17)	0.0134 (15)	0.0039 (14)	0.0059 (13)
C8	0.059 (2)	0.052 (2)	0.0287 (18)	0.0134 (18)	−0.0002 (16)	0.0028 (15)
C9	0.062 (2)	0.050 (2)	0.041 (2)	0.0147 (19)	0.0038 (18)	−0.0018 (17)
C10	0.062 (2)	0.0389 (19)	0.052 (2)	0.0098 (17)	0.0027 (19)	0.0066 (17)
C11	0.062 (2)	0.044 (2)	0.044 (2)	0.0167 (18)	0.0038 (17)	0.0124 (16)
C12	0.0455 (18)	0.0410 (18)	0.0327 (17)	0.0156 (15)	0.0041 (14)	0.0074 (14)
C13	0.058 (2)	0.048 (2)	0.0305 (17)	0.0195 (17)	0.0049 (15)	0.0152 (15)
C14	0.057 (2)	0.061 (2)	0.040 (2)	0.0286 (19)	0.0092 (17)	0.0195 (18)
C15	0.082 (3)	0.145 (6)	0.068 (3)	0.072 (4)	0.026 (3)	0.060 (4)
C16	0.052 (2)	0.071 (3)	0.037 (2)	0.029 (2)	0.0118 (16)	0.0172 (18)
C17	0.080 (3)	0.054 (3)	0.067 (3)	0.022 (2)	−0.006 (3)	−0.004 (2)
C18	0.086 (3)	0.084 (3)	0.040 (2)	0.036 (3)	0.020 (2)	0.026 (2)
Cl1	0.0493 (5)	0.0565 (6)	0.0514 (6)	0.0189 (4)	0.0047 (4)	0.0133 (4)

S1—O1	1.438 (3)	C14—C15	1.516 (9)
S1—O2	1.436 (3)	C14—C16	1.524 (6)
S1—C6	1.733 (4)	C2—H2A	0.9300
S1—C7	1.742 (4)	C3—H3A	0.9300
N1—C1	1.396 (5)	C4—H4A	0.9300
N1—C12	1.394 (5)	C5—H5A	0.9300
N1—C13	1.473 (5)	C8—H8A	0.9300
N2—C16	1.488 (6)	C9—H9A	0.9300
N2—C17	1.491 (7)	C10—H10A	0.9300
N2—C18	1.496 (7)	C11—H11A	0.9300
N2—H2B	0.9100	C13—H13A	0.9700
C1—C6	1.400 (5)	C13—H13B	0.9700
C1—C2	1.417 (6)	C14—H14A	0.9800
C2—C3	1.389 (7)	C15—H15A	0.9600
C3—C4	1.384 (7)	C15—H15B	0.9600
C4—C5	1.379 (7)	C15—H15C	0.9600
C5—C6	1.400 (6)	C16—H16A	0.9700
C7—C8	1.400 (5)	C16—H16B	0.9700
C7—C12	1.401 (5)	C17—H17A	0.9600
C8—C9	1.373 (6)	C17—H17B	0.9600
C9—C10	1.378 (7)	C17—H17C	0.9600
C10—C11	1.380 (7)	C18—H18A	0.9600
C11—C12	1.406 (6)	C18—H18B	0.9600
C13—C14	1.530 (6)	C18—H18C	0.9600
O1—S1—O2	117.1 (2)	C3—C4—H4A	120.00
O1—S1—C6	111.1 (2)	C5—C4—H4A	120.00
O1—S1—C7	110.2 (2)	C4—C5—H5A	120.00
O2—S1—C6	108.2 (2)	C6—C5—H5A	120.00
O2—S1—C7	108.99 (19)	C7—C8—H8A	120.00
C6—S1—C7	99.90 (19)	C9—C8—H8A	120.00
C1—N1—C12	121.7 (3)	C8—C9—H9A	121.00
C1—N1—C13	118.9 (3)	C10—C9—H9A	121.00
C12—N1—C13	119.3 (3)	C9—C10—H10A	119.00
C16—N2—C17	113.2 (4)	C11—C10—H10A	119.00
C16—N2—C18	109.4 (4)	C10—C11—H11A	119.00
C17—N2—C18	110.1 (4)	C12—C11—H11A	120.00
C16—N2—H2B	108.00	N1—C13—H13A	109.00
C17—N2—H2B	108.00	N1—C13—H13B	109.00
C18—N2—H2B	108.00	C14—C13—H13A	109.00
N1—C1—C2	120.7 (3)	C14—C13—H13B	109.00
N1—C1—C6	121.7 (4)	H13A—C13—H13B	108.00
C2—C1—C6	117.6 (4)	C13—C14—H14A	109.00
C1—C2—C3	119.4 (4)	C15—C14—H14A	109.00
C2—C3—C4	122.0 (4)	C16—C14—H14A	109.00
C3—C4—C5	119.6 (5)	C14—C15—H15A	109.00
C4—C5—C6	119.4 (4)	C14—C15—H15B	109.00
S1—C6—C1	118.3 (3)	C14—C15—H15C	110.00
S1—C6—C5	119.3 (3)	H15A—C15—H15B	109.00
C1—C6—C5	122.0 (4)	H15A—C15—H15C	109.00
C8—C7—C12	122.2 (4)	H15B—C15—H15C	110.00
S1—C7—C8	119.0 (3)	N2—C16—H16A	108.00
S1—C7—C12	118.6 (3)	N2—C16—H16B	108.00
C7—C8—C9	119.9 (4)	C14—C16—H16A	108.00
C8—C9—C10	118.8 (4)	C14—C16—H16B	108.00
C9—C10—C11	121.9 (4)	H16A—C16—H16B	107.00
C10—C11—C12	120.9 (4)	N2—C17—H17A	109.00
N1—C12—C7	121.2 (4)	N2—C17—H17B	110.00
N1—C12—C11	122.5 (4)	N2—C17—H17C	110.00
C7—C12—C11	116.2 (4)	H17A—C17—H17B	109.00
N1—C13—C14	112.6 (3)	H17A—C17—H17C	109.00
C13—C14—C15	112.2 (4)	H17B—C17—H17C	109.00
C13—C14—C16	109.1 (4)	N2—C18—H18A	109.00
C15—C14—C16	107.5 (4)	N2—C18—H18B	109.00
N2—C16—C14	115.8 (4)	N2—C18—H18C	109.00
C1—C2—H2A	120.00	H18A—C18—H18B	109.00
C3—C2—H2A	120.00	H18A—C18—H18C	110.00
C2—C3—H3A	119.00	H18B—C18—H18C	110.00
C4—C3—H3A	119.00
O1—S1—C6—C1	154.8 (3)	C6—C1—C2—C3	2.2 (6)
O2—S1—C6—C1	−75.4 (4)	N1—C1—C2—C3	−176.5 (4)
C7—S1—C6—C1	38.5 (4)	N1—C1—C6—C5	175.2 (4)
O1—S1—C6—C5	−32.5 (4)	C2—C1—C6—S1	169.0 (3)
O2—S1—C6—C5	97.4 (4)	C2—C1—C6—C5	−3.5 (6)
C7—S1—C6—C5	−148.7 (3)	C1—C2—C3—C4	−0.1 (7)
O1—S1—C7—C8	30.5 (4)	C2—C3—C4—C5	−0.8 (7)
O2—S1—C7—C8	−99.3 (4)	C3—C4—C5—C6	−0.5 (7)
C6—S1—C7—C8	147.4 (4)	C4—C5—C6—C1	2.7 (7)
O1—S1—C7—C12	−154.8 (3)	C4—C5—C6—S1	−169.7 (4)
O2—S1—C7—C12	75.5 (4)	S1—C7—C12—C11	−172.2 (3)
C6—S1—C7—C12	−37.8 (4)	S1—C7—C12—N1	10.6 (5)
C12—N1—C13—C14	113.2 (4)	C12—C7—C8—C9	−2.4 (7)
C13—N1—C1—C2	−22.4 (6)	S1—C7—C8—C9	172.2 (4)
C12—N1—C1—C6	−24.9 (6)	C8—C7—C12—C11	2.4 (6)
C12—N1—C1—C2	153.8 (4)	C8—C7—C12—N1	−174.9 (4)
C1—N1—C13—C14	−70.6 (5)	C7—C8—C9—C10	0.3 (7)
C13—N1—C12—C7	−158.2 (4)	C8—C9—C10—C11	1.7 (7)
C13—N1—C1—C6	159.0 (4)	C9—C10—C11—C12	−1.6 (7)
C1—N1—C12—C7	25.7 (6)	C10—C11—C12—C7	−0.4 (6)
C1—N1—C12—C11	−151.4 (4)	C10—C11—C12—N1	176.8 (4)
C13—N1—C12—C11	24.8 (6)	N1—C13—C14—C15	−51.8 (6)
C18—N2—C16—C14	165.0 (4)	N1—C13—C14—C16	−170.8 (4)
C17—N2—C16—C14	−71.7 (5)	C15—C14—C16—N2	165.3 (4)
N1—C1—C6—S1	−12.3 (5)	C13—C14—C16—N2	−72.9 (5)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl1	0.91	2.18	3.027 (4)	155
C13—H13A···Cl1i	0.97	2.80	3.608 (4)	141
C13—H13B···Cl1	0.97	2.76	3.692 (4)	161
C17—H17B···Cg2ii	0.96	2.62	3.559 (6)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl1	0.91	2.18	3.027 (4)	155
C13—H13A⋯Cl1i	0.97	2.80	3.608 (4)	141
C13—H13B⋯Cl1	0.97	2.76	3.692 (4)	161
C17—H17B⋯Cg2ii	0.96	2.62	3.559 (6)	166

Symmetry codes: (i) ; (ii) .