10-Methyl-10H-pheno­thia­zine

In the title compound C₁₃H₁₁NS, the pheno­thia­zine unit has a non-planar butterfly structure, and the central six-membered ring adopts a boat conformation. The dihedral angle between the two outer aromatic rings of the pheno­thia­zine unit is 39.53 (10)°. In the crystal, a π–π inter­action with a centroid–centroid distance of 3.6871 (12) Å is observed between the aromatic rings of neighbouring mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.097
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.355 Report

Alert level G
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          72 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

10-Methyl-10H-phenothiazine

Crystal data

C13H11NS	F(000) = 448
Mr = 213.29	Dx = 1.335 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.6245 (7) Å	Cell parameters from 1567 reflections
b = 6.9130 (4) Å	θ = 3.1–29.4°
c = 13.7792 (10) Å	µ = 0.27 mm^−1
β = 106.591 (2)°	T = 296 K
V = 1061.20 (12) Å^3	Block, green
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1567 reflections with I > 2σ(I)
Bruker axs kappa axes2 CCD Diffractometer scans	Rint = 0.018
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 3.1°
Tmin = 0.691, Tmax = 0.746	h = −13→13
10676 measured reflections	k = −8→8
1868 independent reflections	l = −14→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0378P)^2 + 0.6758P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1868 reflections	Δρmax = 0.16 e Å^−3
137 parameters	Δρmin = −0.21 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.86050 (5)	0.40501 (9)	0.04641 (4)	0.0510 (2)
N1	0.73700 (14)	0.7457 (2)	0.09898 (12)	0.0424 (4)
C6	0.71525 (17)	0.4834 (3)	−0.02138 (14)	0.0386 (4)
C7	0.85448 (15)	0.4638 (3)	0.16918 (14)	0.0377 (4)
C2	0.55714 (17)	0.7158 (3)	−0.04584 (15)	0.0435 (5)
H2	0.525007	0.826949	−0.025824	0.052*
C12	0.79493 (15)	0.6314 (3)	0.18380 (14)	0.0375 (4)
C1	0.66956 (16)	0.6503 (3)	0.01080 (14)	0.0363 (4)
C5	0.64954 (19)	0.3852 (3)	−0.10654 (15)	0.0482 (5)
H5	0.680226	0.272801	−0.126692	0.058*
C3	0.49300 (19)	0.6178 (3)	−0.13119 (15)	0.0487 (5)
H3	0.418167	0.663806	−0.168228	0.058*
C11	0.79623 (18)	0.6807 (3)	0.28215 (15)	0.0495 (5)
H11	0.754341	0.788976	0.293389	0.059*
C4	0.5380 (2)	0.4536 (4)	−0.16213 (15)	0.0523 (5)
H4	0.494181	0.388443	−0.219924	0.063*
C8	0.91483 (17)	0.3503 (3)	0.25088 (16)	0.0480 (5)
H8	0.952563	0.236993	0.240176	0.058*
C9	0.9189 (2)	0.4055 (4)	0.34792 (17)	0.0581 (6)
H9	0.961780	0.331961	0.402883	0.070*
C10	0.8596 (2)	0.5690 (4)	0.36327 (17)	0.0596 (6)
H10	0.862047	0.605223	0.428820	0.072*
C13	0.7003 (2)	0.9396 (3)	0.1182 (2)	0.0638 (7)
H13A	0.683800	1.014474	0.057068	0.096*
H13B	0.763616	1.000018	0.169713	0.096*
H13C	0.629368	0.932321	0.140436	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0417 (3)	0.0638 (4)	0.0492 (3)	0.0133 (2)	0.0158 (2)	−0.0065 (3)
N1	0.0440 (9)	0.0328 (8)	0.0465 (10)	0.0017 (7)	0.0065 (7)	−0.0023 (7)
C6	0.0394 (10)	0.0458 (11)	0.0346 (10)	0.0009 (8)	0.0171 (8)	0.0021 (8)
C7	0.0278 (9)	0.0429 (11)	0.0414 (10)	−0.0012 (8)	0.0085 (8)	−0.0006 (8)
C2	0.0444 (11)	0.0406 (11)	0.0446 (11)	0.0053 (9)	0.0113 (9)	0.0091 (9)
C12	0.0288 (9)	0.0412 (10)	0.0403 (10)	−0.0038 (8)	0.0067 (8)	−0.0030 (8)
C1	0.0396 (10)	0.0358 (10)	0.0356 (10)	−0.0015 (8)	0.0142 (8)	0.0051 (8)
C5	0.0557 (13)	0.0537 (13)	0.0388 (11)	−0.0004 (10)	0.0193 (9)	−0.0086 (9)
C3	0.0438 (11)	0.0613 (14)	0.0380 (11)	−0.0014 (10)	0.0070 (9)	0.0113 (10)
C11	0.0401 (11)	0.0613 (13)	0.0452 (12)	0.0002 (10)	0.0095 (9)	−0.0126 (10)
C4	0.0534 (13)	0.0681 (15)	0.0334 (11)	−0.0090 (11)	0.0094 (9)	−0.0032 (10)
C8	0.0348 (10)	0.0490 (12)	0.0552 (13)	0.0011 (9)	0.0048 (9)	0.0060 (10)
C9	0.0428 (12)	0.0780 (17)	0.0464 (13)	−0.0064 (11)	0.0015 (10)	0.0167 (12)
C10	0.0467 (12)	0.0927 (19)	0.0372 (11)	−0.0097 (13)	0.0086 (9)	−0.0066 (12)
C13	0.0721 (16)	0.0369 (12)	0.0734 (16)	0.0045 (11)	0.0061 (13)	−0.0066 (11)

Geometric parameters (Å, º)

S1—C7	1.760 (2)	C5—H5	0.9300
S1—C6	1.7652 (19)	C3—C4	1.368 (3)
N1—C1	1.408 (2)	C3—H3	0.9300
N1—C12	1.412 (2)	C11—C10	1.385 (3)
N1—C13	1.454 (3)	C11—H11	0.9300
C6—C5	1.382 (3)	C4—H4	0.9300
C6—C1	1.395 (3)	C8—C9	1.378 (3)
C7—C8	1.387 (3)	C8—H8	0.9300
C7—C12	1.394 (3)	C9—C10	1.371 (4)
C2—C3	1.377 (3)	C9—H9	0.9300
C2—C1	1.393 (3)	C10—H10	0.9300
C2—H2	0.9300	C13—H13A	0.9600
C12—C11	1.393 (3)	C13—H13B	0.9600
C5—C4	1.387 (3)	C13—H13C	0.9600
C7—S1—C6	98.23 (8)	C4—C3—H3	119.6
C1—N1—C12	117.96 (15)	C2—C3—H3	119.6
C1—N1—C13	117.97 (17)	C10—C11—C12	120.3 (2)
C12—N1—C13	117.42 (17)	C10—C11—H11	119.9
C5—C6—C1	120.53 (18)	C12—C11—H11	119.9
C5—C6—S1	120.80 (16)	C3—C4—C5	119.4 (2)
C1—C6—S1	118.64 (14)	C3—C4—H4	120.3
C8—C7—C12	120.65 (19)	C5—C4—H4	120.3
C8—C7—S1	119.99 (16)	C9—C8—C7	120.0 (2)
C12—C7—S1	119.23 (14)	C9—C8—H8	120.0
C3—C2—C1	120.74 (19)	C7—C8—H8	120.0
C3—C2—H2	119.6	C10—C9—C8	119.9 (2)
C1—C2—H2	119.6	C10—C9—H9	120.1
C11—C12—C7	118.41 (18)	C8—C9—H9	120.1
C11—C12—N1	122.60 (18)	C9—C10—C11	120.7 (2)
C7—C12—N1	118.99 (17)	C9—C10—H10	119.7
C2—C1—C6	118.19 (18)	C11—C10—H10	119.7
C2—C1—N1	122.26 (17)	N1—C13—H13A	109.5
C6—C1—N1	119.55 (16)	N1—C13—H13B	109.5
C6—C5—C4	120.3 (2)	H13A—C13—H13B	109.5
C6—C5—H5	119.9	N1—C13—H13C	109.5
C4—C5—H5	119.9	H13A—C13—H13C	109.5
C4—C3—C2	120.8 (2)	H13B—C13—H13C	109.5
C7—S1—C6—C5	−144.50 (17)	S1—C6—C1—N1	−3.4 (2)
C7—S1—C6—C1	37.60 (17)	C12—N1—C1—C2	136.84 (18)
C6—S1—C7—C8	146.79 (16)	C13—N1—C1—C2	−13.9 (3)
C6—S1—C7—C12	−37.18 (16)	C12—N1—C1—C6	−42.6 (2)
C8—C7—C12—C11	−0.8 (3)	C13—N1—C1—C6	166.72 (19)
S1—C7—C12—C11	−176.84 (14)	C1—C6—C5—C4	1.1 (3)
C8—C7—C12—N1	178.45 (17)	S1—C6—C5—C4	−176.76 (16)
S1—C7—C12—N1	2.4 (2)	C1—C2—C3—C4	0.2 (3)
C1—N1—C12—C11	−137.67 (19)	C7—C12—C11—C10	2.6 (3)
C13—N1—C12—C11	13.2 (3)	N1—C12—C11—C10	−176.63 (19)
C1—N1—C12—C7	43.1 (2)	C2—C3—C4—C5	0.1 (3)
C13—N1—C12—C7	−166.04 (18)	C6—C5—C4—C3	−0.8 (3)
C3—C2—C1—C6	0.1 (3)	C12—C7—C8—C9	−1.6 (3)
C3—C2—C1—N1	−179.31 (18)	S1—C7—C8—C9	174.34 (16)
C5—C6—C1—C2	−0.8 (3)	C7—C8—C9—C10	2.3 (3)
S1—C6—C1—C2	177.16 (14)	C8—C9—C10—C11	−0.5 (3)
C5—C6—C1—N1	178.68 (18)	C12—C11—C10—C9	−2.0 (3)