Crystal structure of 10-ethyl-7-(9-ethyl-9H-carbazol-3-yl)-10H-pheno­thia­zine-3-carbaldehyde

In the title compound, a pheno­thia­zine moiety is linked to a planar carbazole unit (r.m.s. deviation = 0.029 Å) by a C—C single bond. Their mean planes are inclined to one another by 27.28 (5)°, and the pheno­thia­zine moiety possesses a typical butterfly structure with a fold angle of 27.36 (9)° between the two benzene rings.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.107
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          51 % Note
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.          5 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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
   2 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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

10-Ethyl-7-(9-ethyl-9H-carbazol-3-yl)-10H-phenothiazine-3-carbaldehyde

Crystal data

C29H24N2OS	F(000) = 944
Mr = 448.56	Dx = 1.316 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.4677 (6) Å	Cell parameters from 6254 reflections
b = 25.7169 (13) Å	θ = 2.4–23.8°
c = 9.5704 (5) Å	µ = 0.17 mm^−1
β = 103.681 (2)°	T = 296 K
V = 2264.1 (2) Å^3	Block, brown
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2974 reflections with I > 2σ(I)
Bruker axs kappa axes2 CCD scans	Rint = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 25.0°, θmin = 2.3°
Tmin = 0.677, Tmax = 0.745	h = −11→9
25526 measured reflections	k = −30→30
3981 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.8313P] where P = (Fo^2 + 2Fc^2)/3
3981 reflections	(Δ/σ)max = 0.004
300 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 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	0.49912 (6)	0.15680 (2)	0.93196 (6)	0.04721 (18)
N2	0.78333 (17)	0.11025 (6)	1.10224 (16)	0.0385 (4)
C5	0.3217 (2)	−0.16204 (8)	0.5560 (2)	0.0395 (5)
C15	0.5175 (2)	0.01031 (7)	0.7928 (2)	0.0385 (5)
C12	0.4282 (2)	−0.02290 (8)	0.6785 (2)	0.0393 (5)
C10	0.3469 (2)	−0.10671 (8)	0.5781 (2)	0.0380 (5)
C17	0.7263 (2)	0.02401 (8)	0.9923 (2)	0.0423 (5)
H17	0.8081	0.0101	1.0547	0.051*
C18	0.6941 (2)	0.07646 (7)	1.0030 (2)	0.0362 (5)
C23	0.7869 (2)	0.16369 (7)	1.0771 (2)	0.0374 (5)
C21	0.9010 (2)	0.08767 (8)	1.2138 (2)	0.0443 (5)
H21A	0.8654	0.0561	1.2489	0.053*
H21B	0.9253	0.1119	1.2936	0.053*
C28	0.6646 (2)	0.18995 (7)	0.9936 (2)	0.0381 (5)
C16	0.6397 (2)	−0.00788 (8)	0.8909 (2)	0.0424 (5)
H16	0.6642	−0.0428	0.8884	0.051*
N1	0.1914 (2)	−0.11924 (7)	0.35912 (18)	0.0470 (5)
C11	0.4296 (2)	−0.07678 (8)	0.6882 (2)	0.0394 (5)
H11	0.4864	−0.0929	0.7692	0.047*
C26	0.7923 (2)	0.27184 (8)	1.0287 (2)	0.0438 (5)
C27	0.6683 (2)	0.24282 (8)	0.9705 (2)	0.0436 (5)
H27	0.5866	0.2593	0.9152	0.052*
C9	0.2620 (2)	−0.08213 (8)	0.4554 (2)	0.0420 (5)
C19	0.5669 (2)	0.09442 (7)	0.9097 (2)	0.0377 (5)
C20	0.4834 (2)	0.06242 (7)	0.8066 (2)	0.0403 (5)
H20	0.4014	0.0762	0.7442	0.048*
C14	0.2576 (2)	−0.02860 (8)	0.4439 (2)	0.0498 (6)
H14	0.1999	−0.0124	0.3635	0.060*
O1	0.7031 (2)	0.35389 (7)	0.9339 (2)	0.0900 (7)
C13	0.3407 (2)	0.00008 (8)	0.5540 (2)	0.0482 (5)
H13	0.3392	0.0361	0.5463	0.058*
C24	0.9103 (2)	0.19363 (8)	1.1355 (2)	0.0444 (5)
H24	0.9926	0.1776	1.1913	0.053*
C6	0.2262 (2)	−0.16776 (8)	0.4193 (2)	0.0420 (5)
C29	0.8000 (3)	0.32760 (9)	1.0036 (3)	0.0579 (6)
H29	0.8870	0.3443	1.0448	0.069*
C4	0.3684 (2)	−0.20599 (8)	0.6386 (2)	0.0474 (5)
H4	0.4303	−0.2030	0.7295	0.057*
C7	0.0799 (2)	−0.10852 (9)	0.2300 (2)	0.0535 (6)
H7A	0.0743	−0.1375	0.1641	0.064*
H7B	0.1074	−0.0779	0.1836	0.064*
C25	0.9118 (2)	0.24642 (8)	1.1116 (2)	0.0474 (5)
H25	0.9951	0.2654	1.1521	0.057*
C1	0.1828 (2)	−0.21668 (8)	0.3631 (2)	0.0509 (6)
H1	0.1226	−0.2204	0.2716	0.061*
C22	1.0392 (2)	0.07482 (9)	1.1657 (2)	0.0561 (6)
H22A	1.0222	0.0452	1.1028	0.084*
H22B	1.1159	0.0671	1.2483	0.084*
H22C	1.0665	0.1041	1.1156	0.084*
C3	0.3213 (3)	−0.25401 (9)	0.5835 (3)	0.0553 (6)
H3	0.3502	−0.2836	0.6389	0.066*
C2	0.2315 (2)	−0.25924 (9)	0.4470 (3)	0.0560 (6)
H2	0.2037	−0.2923	0.4116	0.067*
C8	−0.0676 (3)	−0.09976 (12)	0.2586 (3)	0.0787 (8)
H8A	−0.0938	−0.1292	0.3088	0.118*
H8B	−0.1380	−0.0954	0.1690	0.118*
H8C	−0.0654	−0.0691	0.3163	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0356 (3)	0.0397 (3)	0.0623 (4)	0.0083 (2)	0.0034 (3)	−0.0034 (3)
N2	0.0359 (10)	0.0368 (9)	0.0398 (9)	0.0067 (7)	0.0032 (8)	0.0026 (7)
C5	0.0376 (12)	0.0409 (11)	0.0417 (11)	0.0010 (9)	0.0125 (9)	0.0006 (9)
C15	0.0387 (12)	0.0376 (11)	0.0420 (11)	0.0009 (9)	0.0150 (9)	0.0031 (9)
C12	0.0394 (12)	0.0407 (11)	0.0399 (11)	0.0002 (9)	0.0133 (9)	0.0028 (9)
C10	0.0378 (11)	0.0404 (11)	0.0376 (11)	0.0033 (9)	0.0123 (9)	0.0023 (9)
C17	0.0382 (12)	0.0389 (11)	0.0473 (12)	0.0075 (9)	0.0052 (10)	0.0064 (9)
C18	0.0345 (11)	0.0367 (11)	0.0388 (11)	0.0034 (9)	0.0114 (9)	0.0044 (9)
C23	0.0377 (11)	0.0403 (11)	0.0346 (10)	0.0066 (9)	0.0093 (9)	−0.0006 (9)
C21	0.0448 (13)	0.0438 (12)	0.0404 (11)	0.0086 (10)	0.0023 (10)	0.0043 (9)
C28	0.0386 (12)	0.0393 (11)	0.0358 (11)	0.0042 (9)	0.0072 (9)	−0.0033 (9)
C16	0.0438 (13)	0.0337 (11)	0.0503 (12)	0.0038 (9)	0.0124 (10)	0.0026 (9)
N1	0.0502 (11)	0.0465 (10)	0.0401 (9)	−0.0018 (8)	0.0023 (8)	0.0029 (8)
C11	0.0397 (12)	0.0425 (12)	0.0362 (11)	0.0041 (9)	0.0094 (9)	0.0048 (9)
C26	0.0512 (13)	0.0419 (12)	0.0379 (11)	0.0036 (10)	0.0096 (10)	−0.0023 (9)
C27	0.0469 (13)	0.0407 (12)	0.0394 (11)	0.0081 (10)	0.0026 (10)	0.0002 (9)
C9	0.0457 (13)	0.0424 (12)	0.0380 (11)	−0.0021 (10)	0.0103 (10)	0.0034 (9)
C19	0.0353 (11)	0.0365 (11)	0.0418 (11)	0.0047 (9)	0.0104 (9)	0.0034 (9)
C20	0.0348 (11)	0.0417 (12)	0.0429 (11)	0.0041 (9)	0.0060 (9)	0.0051 (9)
C14	0.0568 (14)	0.0477 (13)	0.0408 (12)	0.0019 (11)	0.0032 (11)	0.0104 (10)
O1	0.0925 (15)	0.0504 (11)	0.1099 (16)	0.0041 (10)	−0.0101 (13)	0.0203 (11)
C13	0.0585 (15)	0.0379 (11)	0.0474 (12)	0.0016 (10)	0.0109 (11)	0.0065 (10)
C24	0.0384 (12)	0.0436 (12)	0.0476 (12)	0.0065 (10)	0.0034 (10)	−0.0025 (10)
C6	0.0371 (12)	0.0443 (12)	0.0453 (12)	−0.0021 (9)	0.0112 (9)	0.0009 (10)
C29	0.0669 (17)	0.0443 (13)	0.0594 (15)	−0.0015 (12)	0.0087 (13)	0.0006 (12)
C4	0.0461 (13)	0.0454 (13)	0.0497 (12)	0.0033 (10)	0.0095 (10)	0.0051 (10)
C7	0.0557 (15)	0.0612 (14)	0.0395 (12)	−0.0032 (11)	0.0035 (11)	0.0043 (11)
C25	0.0450 (13)	0.0477 (12)	0.0479 (12)	−0.0027 (10)	0.0076 (10)	−0.0064 (10)
C1	0.0441 (13)	0.0527 (14)	0.0539 (13)	−0.0096 (11)	0.0074 (11)	−0.0053 (11)
C22	0.0432 (13)	0.0576 (14)	0.0610 (15)	0.0145 (11)	−0.0006 (11)	−0.0043 (12)
C3	0.0539 (15)	0.0431 (13)	0.0692 (16)	−0.0002 (11)	0.0152 (13)	0.0084 (11)
C2	0.0500 (14)	0.0444 (13)	0.0740 (17)	−0.0101 (11)	0.0154 (13)	−0.0058 (12)
C8	0.0529 (17)	0.099 (2)	0.0816 (19)	0.0087 (15)	0.0108 (14)	0.0031 (17)

Geometric parameters (Å, º)

S1—C28	1.759 (2)	C26—C27	1.392 (3)
S1—C19	1.7595 (19)	C26—C29	1.459 (3)
N2—C23	1.397 (2)	C27—H27	0.9300
N2—C18	1.412 (2)	C9—C14	1.381 (3)
N2—C21	1.468 (2)	C19—C20	1.381 (3)
C5—C4	1.390 (3)	C20—H20	0.9300
C5—C6	1.411 (3)	C14—C13	1.372 (3)
C5—C10	1.450 (3)	C14—H14	0.9300
C15—C16	1.387 (3)	O1—C29	1.206 (3)
C15—C20	1.392 (3)	C13—H13	0.9300
C15—C12	1.485 (3)	C24—C25	1.377 (3)
C12—C11	1.388 (3)	C24—H24	0.9300
C12—C13	1.410 (3)	C6—C1	1.392 (3)
C10—C11	1.388 (3)	C29—H29	0.9300
C10—C9	1.406 (3)	C4—C3	1.375 (3)
C17—C16	1.382 (3)	C4—H4	0.9300
C17—C18	1.392 (3)	C7—C8	1.502 (3)
C17—H17	0.9300	C7—H7A	0.9700
C18—C19	1.397 (3)	C7—H7B	0.9700
C23—C24	1.400 (3)	C25—H25	0.9300
C23—C28	1.413 (3)	C1—C2	1.371 (3)
C21—C22	1.522 (3)	C1—H1	0.9300
C21—H21A	0.9700	C22—H22A	0.9600
C21—H21B	0.9700	C22—H22B	0.9600
C28—C27	1.379 (3)	C22—H22C	0.9600
C16—H16	0.9300	C3—C2	1.386 (3)
N1—C6	1.381 (3)	C3—H3	0.9300
N1—C9	1.384 (3)	C2—H2	0.9300
N1—C7	1.449 (3)	C8—H8A	0.9600
C11—H11	0.9300	C8—H8B	0.9600
C26—C25	1.383 (3)	C8—H8C	0.9600
C28—S1—C19	99.26 (9)	C20—C19—S1	117.78 (14)
C23—N2—C18	121.66 (15)	C18—C19—S1	120.54 (15)
C23—N2—C21	117.98 (16)	C19—C20—C15	122.33 (18)
C18—N2—C21	118.46 (15)	C19—C20—H20	118.8
C4—C5—C6	119.35 (19)	C15—C20—H20	118.8
C4—C5—C10	134.10 (19)	C13—C14—C9	118.27 (19)
C6—C5—C10	106.54 (17)	C13—C14—H14	120.9
C16—C15—C20	115.82 (18)	C9—C14—H14	120.9
C16—C15—C12	122.90 (18)	C14—C13—C12	122.65 (19)
C20—C15—C12	121.28 (18)	C14—C13—H13	118.7
C11—C12—C13	117.99 (18)	C12—C13—H13	118.7
C11—C12—C15	122.01 (17)	C25—C24—C23	121.09 (19)
C13—C12—C15	119.99 (18)	C25—C24—H24	119.5
C11—C10—C9	119.55 (18)	C23—C24—H24	119.5
C11—C10—C5	134.33 (18)	N1—C6—C1	129.5 (2)
C9—C10—C5	106.12 (17)	N1—C6—C5	109.26 (17)
C16—C17—C18	121.50 (18)	C1—C6—C5	121.24 (19)
C16—C17—H17	119.3	O1—C29—C26	125.5 (2)
C18—C17—H17	119.3	O1—C29—H29	117.2
C17—C18—C19	116.38 (18)	C26—C29—H29	117.2
C17—C18—N2	122.63 (17)	C3—C4—C5	118.8 (2)
C19—C18—N2	120.99 (17)	C3—C4—H4	120.6
N2—C23—C24	121.61 (17)	C5—C4—H4	120.6
N2—C23—C28	121.17 (18)	N1—C7—C8	113.25 (19)
C24—C23—C28	117.21 (18)	N1—C7—H7A	108.9
N2—C21—C22	115.14 (17)	C8—C7—H7A	108.9
N2—C21—H21A	108.5	N1—C7—H7B	108.9
C22—C21—H21A	108.5	C8—C7—H7B	108.9
N2—C21—H21B	108.5	H7A—C7—H7B	107.7
C22—C21—H21B	108.5	C24—C25—C26	121.5 (2)
H21A—C21—H21B	107.5	C24—C25—H25	119.3
C27—C28—C23	120.91 (19)	C26—C25—H25	119.3
C27—C28—S1	118.57 (15)	C2—C1—C6	117.9 (2)
C23—C28—S1	120.23 (15)	C2—C1—H1	121.1
C17—C16—C15	122.44 (18)	C6—C1—H1	121.1
C17—C16—H16	118.8	C21—C22—H22A	109.5
C15—C16—H16	118.8	C21—C22—H22B	109.5
C6—N1—C9	108.37 (16)	H22A—C22—H22B	109.5
C6—N1—C7	125.54 (18)	C21—C22—H22C	109.5
C9—N1—C7	125.18 (18)	H22A—C22—H22C	109.5
C12—C11—C10	120.52 (18)	H22B—C22—H22C	109.5
C12—C11—H11	119.7	C4—C3—C2	121.3 (2)
C10—C11—H11	119.7	C4—C3—H3	119.4
C25—C26—C27	118.33 (19)	C2—C3—H3	119.4
C25—C26—C29	119.6 (2)	C1—C2—C3	121.4 (2)
C27—C26—C29	122.1 (2)	C1—C2—H2	119.3
C28—C27—C26	121.00 (19)	C3—C2—H2	119.3
C28—C27—H27	119.5	C7—C8—H8A	109.5
C26—C27—H27	119.5	C7—C8—H8B	109.5
C14—C9—N1	129.31 (18)	H8A—C8—H8B	109.5
C14—C9—C10	121.02 (19)	C7—C8—H8C	109.5
N1—C9—C10	109.67 (17)	H8A—C8—H8C	109.5
C20—C19—C18	121.40 (18)	H8B—C8—H8C	109.5
C16—C15—C12—C11	21.4 (3)	C5—C10—C9—C14	178.0 (2)
C20—C15—C12—C11	−159.25 (19)	C11—C10—C9—N1	178.85 (18)
C16—C15—C12—C13	−157.3 (2)	C5—C10—C9—N1	−2.0 (2)
C20—C15—C12—C13	22.1 (3)	C17—C18—C19—C20	−4.0 (3)
C4—C5—C10—C11	1.8 (4)	N2—C18—C19—C20	176.20 (18)
C6—C5—C10—C11	−179.4 (2)	C17—C18—C19—S1	169.74 (15)
C4—C5—C10—C9	−177.1 (2)	N2—C18—C19—S1	−10.1 (3)
C6—C5—C10—C9	1.7 (2)	C28—S1—C19—C20	−151.56 (16)
C16—C17—C18—C19	2.3 (3)	C28—S1—C19—C18	34.50 (18)
C16—C17—C18—N2	−177.84 (18)	C18—C19—C20—C15	2.3 (3)
C23—N2—C18—C17	153.75 (19)	S1—C19—C20—C15	−171.57 (16)
C21—N2—C18—C17	−10.2 (3)	C16—C15—C20—C19	1.1 (3)
C23—N2—C18—C19	−26.4 (3)	C12—C15—C20—C19	−178.31 (19)
C21—N2—C18—C19	169.58 (18)	N1—C9—C14—C13	−178.6 (2)
C18—N2—C23—C24	−152.34 (19)	C10—C9—C14—C13	1.3 (3)
C21—N2—C23—C24	11.7 (3)	C9—C14—C13—C12	−0.9 (3)
C18—N2—C23—C28	28.8 (3)	C11—C12—C13—C14	0.2 (3)
C21—N2—C23—C28	−167.15 (17)	C15—C12—C13—C14	178.9 (2)
C23—N2—C21—C22	−83.2 (2)	N2—C23—C24—C25	−179.10 (19)
C18—N2—C21—C22	81.4 (2)	C28—C23—C24—C25	−0.2 (3)
N2—C23—C28—C27	179.27 (18)	C9—N1—C6—C1	−179.4 (2)
C24—C23—C28—C27	0.4 (3)	C7—N1—C6—C1	11.1 (4)
N2—C23—C28—S1	5.6 (3)	C9—N1—C6—C5	−0.6 (2)
C24—C23—C28—S1	−173.33 (15)	C7—N1—C6—C5	−170.09 (19)
C19—S1—C28—C27	153.97 (16)	C4—C5—C6—N1	178.28 (19)
C19—S1—C28—C23	−32.19 (17)	C10—C5—C6—N1	−0.7 (2)
C18—C17—C16—C15	1.1 (3)	C4—C5—C6—C1	−2.8 (3)
C20—C15—C16—C17	−2.8 (3)	C10—C5—C6—C1	178.24 (19)
C12—C15—C16—C17	176.64 (19)	C25—C26—C29—O1	−179.7 (2)
C13—C12—C11—C10	0.0 (3)	C27—C26—C29—O1	0.9 (4)
C15—C12—C11—C10	−178.71 (18)	C6—C5—C4—C3	0.8 (3)
C9—C10—C11—C12	0.4 (3)	C10—C5—C4—C3	179.5 (2)
C5—C10—C11—C12	−178.4 (2)	C6—N1—C7—C8	87.7 (3)
C23—C28—C27—C26	0.0 (3)	C9—N1—C7—C8	−80.1 (3)
S1—C28—C27—C26	173.83 (16)	C23—C24—C25—C26	−0.4 (3)
C25—C26—C27—C28	−0.6 (3)	C27—C26—C25—C24	0.8 (3)
C29—C26—C27—C28	178.8 (2)	C29—C26—C25—C24	−178.6 (2)
C6—N1—C9—C14	−178.4 (2)	N1—C6—C1—C2	−178.9 (2)
C7—N1—C9—C14	−8.8 (4)	C5—C6—C1—C2	2.4 (3)
C6—N1—C9—C10	1.7 (2)	C5—C4—C3—C2	1.4 (3)
C7—N1—C9—C10	171.23 (19)	C6—C1—C2—C3	−0.1 (3)
C11—C10—C9—C14	−1.1 (3)	C4—C3—C2—C1	−1.9 (4)

Hydrogen-bond geometry (Å, º)

Cg3 and Cg4 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···Cg4^i	0.97	2.95	3.596 (2)	125
C25—H25···Cg3^ii	0.93	2.96	3.558 (2)	123

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+3/2, y+1/2, −z+3/2.