Crystal structures of three substituted 3-aryl-2-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-ones

The crystal structures of three closely related benzo­thia­zinone structures are reported. All three are conformationally similar having screw-boat puckering in the thia­zine ring and C—H...π-type inter­molecular inter­actions in the crystals.

Computing details

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for (I); SHELXL97 (Sheldrick, 2008) for (II); SHELXL014 (Sheldrick, 2015) for (III). For all compounds, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I) 3-(4-Methoxyphenyl)-2-phenyl-4H-1,3-benzothiazin-4-one

Crystal data

C21H17NO2S	F(000) = 1456
Mr = 347.42	Dx = 1.328 Mg m^−3
Monoclinic, C2/c	Melting point = 365–369 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.820 (4) Å	Cell parameters from 4847 reflections
b = 11.016 (3) Å	θ = 2.3–28.3°
c = 17.890 (4) Å	µ = 0.20 mm^−1
β = 98.385 (5)°	T = 298 K
V = 3474.4 (15) Å^3	Block, colorless
Z = 8	0.26 × 0.24 × 0.12 mm

Data collection

Bruker CCD area-detector diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	3414 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→23
Tmin = 0.940, Tmax = 0.986	k = −14→14
15005 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 0.7957P] where P = (Fo^2 + 2Fc^2)/3
4284 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. Absorption correction: SADABS (Bruker, 2001) was used for absorption correction. R(int) was 0.0415 before and 0.0233 after correction. The λ/2 correction factor is 0.0015.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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.

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

	x	y	z	Uiso*/Ueq
C1	0.17986 (7)	0.37162 (13)	0.33545 (8)	0.0429 (3)
H1	0.1812	0.3332	0.3850	0.052*
C2	0.28205 (7)	0.42680 (12)	0.26124 (7)	0.0387 (3)
C3	0.22572 (8)	0.41320 (12)	0.19132 (8)	0.0411 (3)
C4	0.16382 (8)	0.33411 (13)	0.18637 (8)	0.0453 (3)
C5	0.11974 (9)	0.31295 (16)	0.11634 (10)	0.0604 (4)
H5	0.0793	0.2588	0.1126	0.072*
C6	0.13587 (11)	0.3717 (2)	0.05331 (10)	0.0709 (5)
H6	0.1068	0.3565	0.0068	0.085*
C7	0.19525 (11)	0.4538 (2)	0.05825 (10)	0.0689 (5)
H7	0.2047	0.4957	0.0155	0.083*
C8	0.24026 (9)	0.47316 (15)	0.12662 (8)	0.0529 (4)
H8	0.2808	0.5270	0.1295	0.063*
C9	0.12871 (7)	0.48211 (12)	0.33619 (7)	0.0395 (3)
C10	0.15308 (9)	0.59940 (14)	0.32618 (9)	0.0491 (3)
H10	0.2023	0.6131	0.3168	0.059*
C11	0.10443 (10)	0.69663 (15)	0.33011 (10)	0.0571 (4)
H11	0.1213	0.7752	0.3232	0.068*
C12	0.03146 (10)	0.67779 (16)	0.34414 (10)	0.0578 (4)
H12	−0.0010	0.7433	0.3469	0.069*
C13	0.00683 (9)	0.56148 (16)	0.35406 (10)	0.0562 (4)
H13	−0.0425	0.5484	0.3635	0.067*
C14	0.05456 (8)	0.46423 (15)	0.35005 (8)	0.0484 (3)
H14	0.0372	0.3859	0.3567	0.058*
C15	0.31352 (7)	0.39619 (13)	0.39612 (7)	0.0405 (3)
C16	0.34533 (10)	0.28627 (14)	0.42046 (9)	0.0530 (4)
H16	0.3329	0.2165	0.3921	0.064*
C17	0.39550 (10)	0.27956 (15)	0.48685 (9)	0.0568 (4)
H17	0.4167	0.2053	0.5031	0.068*
C18	0.41438 (8)	0.38303 (14)	0.52936 (7)	0.0441 (3)
C19	0.38413 (9)	0.49301 (14)	0.50441 (9)	0.0499 (4)
H19	0.3975	0.5632	0.5320	0.060*
C20	0.33346 (8)	0.49867 (13)	0.43761 (9)	0.0492 (4)
H20	0.3128	0.5731	0.4209	0.059*
C21	0.48531 (10)	0.46879 (18)	0.64109 (9)	0.0625 (5)
H21A	0.5066	0.5295	0.6119	0.094*
H21B	0.5224	0.4448	0.6829	0.094*
H21C	0.4416	0.5014	0.6598	0.094*
N1	0.25868 (6)	0.39985 (11)	0.32831 (6)	0.0424 (3)
O1	0.34743 (5)	0.45779 (10)	0.25787 (6)	0.0511 (3)
O2	0.46342 (7)	0.36572 (11)	0.59465 (6)	0.0601 (3)
S1	0.14215 (2)	0.25763 (3)	0.26647 (3)	0.05493 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0365 (7)	0.0455 (7)	0.0465 (7)	−0.0048 (6)	0.0049 (6)	0.0087 (6)
C2	0.0370 (7)	0.0353 (6)	0.0438 (7)	0.0003 (5)	0.0057 (5)	−0.0008 (5)
C3	0.0392 (7)	0.0404 (7)	0.0431 (7)	0.0045 (6)	0.0043 (5)	−0.0041 (5)
C4	0.0393 (7)	0.0398 (7)	0.0558 (8)	0.0048 (6)	0.0040 (6)	−0.0100 (6)
C5	0.0439 (8)	0.0628 (10)	0.0712 (11)	0.0028 (8)	−0.0025 (7)	−0.0260 (9)
C6	0.0614 (11)	0.0961 (15)	0.0507 (9)	0.0139 (10)	−0.0065 (8)	−0.0204 (9)
C7	0.0690 (12)	0.0926 (14)	0.0445 (8)	0.0150 (11)	0.0065 (8)	0.0023 (9)
C8	0.0531 (9)	0.0593 (9)	0.0465 (8)	0.0037 (7)	0.0083 (7)	0.0012 (7)
C9	0.0349 (6)	0.0451 (7)	0.0379 (6)	−0.0037 (6)	0.0031 (5)	0.0028 (5)
C10	0.0403 (7)	0.0490 (8)	0.0594 (8)	−0.0051 (6)	0.0116 (6)	0.0050 (7)
C11	0.0588 (10)	0.0440 (8)	0.0702 (10)	−0.0028 (7)	0.0151 (8)	0.0016 (7)
C12	0.0535 (9)	0.0549 (9)	0.0662 (10)	0.0077 (8)	0.0126 (8)	−0.0030 (8)
C13	0.0381 (8)	0.0645 (10)	0.0678 (10)	−0.0003 (7)	0.0135 (7)	0.0004 (8)
C14	0.0399 (7)	0.0506 (8)	0.0556 (8)	−0.0065 (6)	0.0097 (6)	0.0043 (6)
C15	0.0350 (7)	0.0462 (7)	0.0398 (6)	0.0015 (6)	0.0040 (5)	0.0035 (5)
C16	0.0606 (10)	0.0422 (8)	0.0521 (8)	0.0055 (7)	−0.0059 (7)	−0.0043 (6)
C17	0.0659 (10)	0.0439 (8)	0.0553 (9)	0.0126 (7)	−0.0089 (8)	0.0021 (7)
C18	0.0383 (7)	0.0537 (8)	0.0397 (6)	0.0043 (6)	0.0039 (5)	0.0015 (6)
C19	0.0502 (8)	0.0452 (8)	0.0521 (8)	0.0014 (6)	−0.0001 (7)	−0.0062 (6)
C20	0.0476 (8)	0.0415 (8)	0.0558 (8)	0.0054 (6)	−0.0015 (7)	0.0037 (6)
C21	0.0509 (9)	0.0859 (13)	0.0483 (8)	0.0029 (9)	−0.0013 (7)	−0.0147 (8)
N1	0.0325 (6)	0.0506 (7)	0.0432 (6)	−0.0013 (5)	0.0028 (4)	0.0065 (5)
O1	0.0384 (5)	0.0636 (7)	0.0520 (6)	−0.0094 (5)	0.0083 (4)	−0.0003 (5)
O2	0.0631 (7)	0.0654 (7)	0.0461 (6)	0.0108 (6)	−0.0111 (5)	−0.0018 (5)
S1	0.0508 (2)	0.0384 (2)	0.0756 (3)	−0.00997 (16)	0.00913 (19)	−0.00040 (17)

Geometric parameters (Å, º)

C1—N1	1.4622 (17)	C11—H11	0.9300
C1—C9	1.522 (2)	C12—C13	1.374 (2)
C1—S1	1.8192 (15)	C12—H12	0.9300
C1—H1	0.9800	C13—C14	1.376 (2)
C2—O1	1.2240 (16)	C13—H13	0.9300
C2—N1	1.3591 (18)	C14—H14	0.9300
C2—C3	1.4929 (18)	C15—C20	1.369 (2)
C3—C8	1.389 (2)	C15—C16	1.380 (2)
C3—C4	1.398 (2)	C15—N1	1.4432 (17)
C4—C5	1.398 (2)	C16—C17	1.380 (2)
C4—S1	1.7533 (16)	C16—H16	0.9300
C5—C6	1.367 (3)	C17—C18	1.384 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.385 (3)	C18—O2	1.3661 (17)
C6—H6	0.9300	C18—C19	1.374 (2)
C7—C8	1.378 (2)	C19—C20	1.390 (2)
C7—H7	0.9300	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.383 (2)	C21—O2	1.427 (2)
C9—C14	1.3935 (19)	C21—H21A	0.9600
C10—C11	1.386 (2)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
C11—C12	1.376 (2)
N1—C1—C9	114.51 (11)	C13—C12—H12	120.2
N1—C1—S1	110.61 (10)	C11—C12—H12	120.2
C9—C1—S1	113.29 (9)	C12—C13—C14	120.51 (15)
N1—C1—H1	105.9	C12—C13—H13	119.7
C9—C1—H1	105.9	C14—C13—H13	119.7
S1—C1—H1	105.9	C13—C14—C9	120.56 (15)
O1—C2—N1	121.40 (12)	C13—C14—H14	119.7
O1—C2—C3	121.02 (12)	C9—C14—H14	119.7
N1—C2—C3	117.56 (12)	C20—C15—C16	119.35 (13)
C8—C3—C4	118.99 (13)	C20—C15—N1	121.54 (12)
C8—C3—C2	117.78 (13)	C16—C15—N1	119.10 (12)
C4—C3—C2	122.92 (13)	C15—C16—C17	120.20 (14)
C5—C4—C3	119.71 (15)	C15—C16—H16	119.9
C5—C4—S1	119.37 (13)	C17—C16—H16	119.9
C3—C4—S1	120.89 (11)	C16—C17—C18	120.24 (14)
C6—C5—C4	120.15 (17)	C16—C17—H17	119.9
C6—C5—H5	119.9	C18—C17—H17	119.9
C4—C5—H5	119.9	O2—C18—C19	124.93 (14)
C5—C6—C7	120.48 (16)	O2—C18—C17	115.38 (13)
C5—C6—H6	119.8	C19—C18—C17	119.68 (13)
C7—C6—H6	119.8	C18—C19—C20	119.59 (14)
C8—C7—C6	119.88 (17)	C18—C19—H19	120.2
C8—C7—H7	120.1	C20—C19—H19	120.2
C6—C7—H7	120.1	C15—C20—C19	120.91 (14)
C7—C8—C3	120.71 (16)	C15—C20—H20	119.5
C7—C8—H8	119.6	C19—C20—H20	119.5
C3—C8—H8	119.6	O2—C21—H21A	109.5
C10—C9—C14	118.62 (14)	O2—C21—H21B	109.5
C10—C9—C1	123.11 (12)	H21A—C21—H21B	109.5
C14—C9—C1	118.24 (13)	O2—C21—H21C	109.5
C9—C10—C11	120.31 (14)	H21A—C21—H21C	109.5
C9—C10—H10	119.8	H21B—C21—H21C	109.5
C11—C10—H10	119.8	C2—N1—C15	119.41 (11)
C12—C11—C10	120.50 (15)	C2—N1—C1	123.07 (11)
C12—C11—H11	119.8	C15—N1—C1	117.51 (10)
C10—C11—H11	119.8	C18—O2—C21	118.24 (13)
C13—C12—C11	119.50 (16)	C4—S1—C1	96.84 (7)
O1—C2—C3—C8	−20.9 (2)	N1—C15—C16—C17	−177.27 (15)
N1—C2—C3—C8	161.10 (13)	C15—C16—C17—C18	−0.1 (3)
O1—C2—C3—C4	152.55 (14)	C16—C17—C18—O2	178.86 (16)
N1—C2—C3—C4	−25.42 (19)	C16—C17—C18—C19	−1.3 (3)
C8—C3—C4—C5	2.6 (2)	O2—C18—C19—C20	−178.67 (14)
C2—C3—C4—C5	−170.80 (13)	C17—C18—C19—C20	1.5 (2)
C8—C3—C4—S1	−179.16 (11)	C16—C15—C20—C19	−1.2 (2)
C2—C3—C4—S1	7.43 (18)	N1—C15—C20—C19	177.45 (13)
C3—C4—C5—C6	−1.7 (2)	C18—C19—C20—C15	−0.3 (2)
S1—C4—C5—C6	−179.94 (13)	O1—C2—N1—C15	−6.1 (2)
C4—C5—C6—C7	−0.8 (3)	C3—C2—N1—C15	171.89 (12)
C5—C6—C7—C8	2.4 (3)	O1—C2—N1—C1	175.13 (13)
C6—C7—C8—C3	−1.5 (3)	C3—C2—N1—C1	−6.91 (19)
C4—C3—C8—C7	−1.0 (2)	C20—C15—N1—C2	86.36 (17)
C2—C3—C8—C7	172.71 (14)	C16—C15—N1—C2	−95.04 (17)
N1—C1—C9—C10	3.89 (19)	C20—C15—N1—C1	−94.78 (16)
S1—C1—C9—C10	−124.24 (13)	C16—C15—N1—C1	83.83 (17)
N1—C1—C9—C14	−173.97 (12)	C9—C1—N1—C2	−80.00 (16)
S1—C1—C9—C14	57.90 (15)	S1—C1—N1—C2	49.48 (16)
C14—C9—C10—C11	0.1 (2)	C9—C1—N1—C15	101.18 (14)
C1—C9—C10—C11	−177.71 (14)	S1—C1—N1—C15	−129.34 (11)
C9—C10—C11—C12	0.1 (3)	C19—C18—O2—C21	0.1 (2)
C10—C11—C12—C13	−0.2 (3)	C17—C18—O2—C21	179.91 (15)
C11—C12—C13—C14	0.0 (3)	C5—C4—S1—C1	−152.63 (12)
C12—C13—C14—C9	0.3 (2)	C3—C4—S1—C1	29.14 (12)
C10—C9—C14—C13	−0.3 (2)	N1—C1—S1—C4	−54.14 (10)
C1—C9—C14—C13	177.63 (13)	C9—C1—S1—C4	75.99 (10)
C20—C15—C16—C17	1.4 (2)

Hydrogen-bond geometry (Å, º)

Cg(X) = center of gravity of ring (X); D—H···CgX = angle of the D—H bond with the π plane

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.93	2.59	3.447 (2)	154
C21—H21B···O1^ii	0.96	2.63	3.352 (2)	132
C5—H5···O2^iii	0.93	2.46	3.387 (2)	173
C21—H21A···Cg4^iv	0.96	2.96	3.8068 (10)	148

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

(II) 2-Phenyl-3-[4-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1,3-benzothiazin-4-one toluene hemisolvate

Crystal data

2C21H14F3NOS·C7H8	Dx = 1.371 Mg m^−3
Mr = 862.92	Melting point = 404–406 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.953 (2) Å	Cell parameters from 6665 reflections
b = 14.516 (3) Å	θ = 2.2–28.2°
c = 24.546 (5) Å	µ = 0.20 mm^−1
β = 101.024 (4)°	T = 298 K
V = 4180.5 (14) Å^3	Needle, colourless
Z = 4	0.29 × 0.09 × 0.07 mm
F(000) = 1784

Data collection

Bruker CCD area-detector diffractometer	10359 independent reflections
Radiation source: fine-focus sealed tube	8329 reflections with I > 2˘I)
Graphite monochromator	Rint = 0.052
phi and ω scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.592, Tmax = 0.920	k = −19→19
39335 measured reflections	l = −32→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.133	H-atom parameters constrained
wR(F^2) = 0.240	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 8.2026P] where P = (Fo^2 + 2Fc^2)/3
S = 1.31	(Δ/σ)max = 0.001
10359 reflections	Δρmax = 0.48 e Å^−3
580 parameters	Δρmin = −0.34 e Å^−3
74 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

Special details

Experimental. Absorption correction: SADABS (Bruker, 2001) was used for absorption correction. R(int) was 0.0709 before and 0.0303 after correction. The Ratio of minimum to maximum transmission is 0.5920. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7415 (3)	1.0190 (3)	0.11278 (17)	0.0326 (9)
H1	0.6834	0.9719	0.1005	0.039*
C2	0.9318 (3)	1.0494 (3)	0.09051 (15)	0.0292 (8)
C3	0.9144 (3)	1.1495 (3)	0.10152 (15)	0.0296 (9)
C4	0.8087 (4)	1.1904 (3)	0.09618 (16)	0.0347 (9)
C5	0.8013 (5)	1.2859 (3)	0.10036 (19)	0.0498 (12)
H5	0.7301	1.3140	0.0959	0.060*
C6	0.8979 (5)	1.3387 (3)	0.1109 (2)	0.0597 (15)
H6	0.8919	1.4024	0.1134	0.072*
C7	1.0031 (5)	1.2988 (3)	0.1178 (2)	0.0549 (14)
H7	1.0684	1.3350	0.1257	0.066*
C8	1.0120 (4)	1.2042 (3)	0.11295 (18)	0.0417 (11)
H8	1.0836	1.1770	0.1173	0.050*
C9	0.7581 (4)	1.0210 (3)	0.17549 (17)	0.0374 (10)
C10	0.6620 (5)	1.0249 (4)	0.1991 (2)	0.0641 (16)
H10	0.5901	1.0276	0.1765	0.077*
C11	0.6725 (8)	1.0247 (5)	0.2565 (3)	0.094 (3)
H11	0.6076	1.0267	0.2721	0.113*
C12	0.7777 (8)	1.0216 (5)	0.2900 (3)	0.095 (3)
H12	0.7841	1.0226	0.3284	0.114*
C13	0.8724 (6)	1.0169 (4)	0.2676 (2)	0.0735 (18)
H13	0.9440	1.0139	0.2904	0.088*
C14	0.8622 (5)	1.0166 (4)	0.21027 (19)	0.0520 (13)
H14	0.9277	1.0134	0.1951	0.062*
C15	0.8522 (3)	0.8954 (3)	0.07876 (15)	0.0287 (8)
C16	0.8250 (4)	0.8292 (3)	0.11498 (18)	0.0410 (11)
H16	0.7999	0.8472	0.1470	0.049*
C17	0.8350 (4)	0.7373 (3)	0.10367 (19)	0.0449 (11)
H17	0.8168	0.6931	0.1280	0.054*
C18	0.8718 (4)	0.7104 (3)	0.05646 (18)	0.0368 (10)
C19	0.8959 (3)	0.7756 (3)	0.01947 (17)	0.0325 (9)
H19	0.9187	0.7571	−0.0130	0.039*
C20	0.8862 (3)	0.8678 (3)	0.03046 (15)	0.0307 (9)
H20	0.9024	0.9117	0.0054	0.037*
C21	0.8898 (5)	0.6098 (3)	0.0469 (2)	0.0543 (13)
F1	0.8004 (3)	0.5593 (2)	0.05201 (19)	0.0934 (13)
F2	0.9121 (5)	0.5909 (2)	−0.00173 (17)	0.1125 (17)
F3	0.9745 (3)	0.5749 (2)	0.08345 (19)	0.1020 (15)
N1	0.8416 (3)	0.9909 (2)	0.09121 (13)	0.0287 (7)
O1	1.0226 (2)	1.0219 (2)	0.08167 (14)	0.0426 (8)
S1	0.68361 (9)	1.12577 (9)	0.08114 (5)	0.0443 (3)
C22	0.2359 (3)	0.8724 (3)	0.09757 (16)	0.0312 (9)
H22	0.1793	0.9219	0.0944	0.037*
C23	0.4274 (3)	0.8614 (3)	0.07246 (14)	0.0259 (8)
C24	0.4087 (3)	0.7606 (3)	0.06289 (15)	0.0288 (8)
C25	0.3015 (4)	0.7208 (3)	0.05029 (16)	0.0361 (10)
C26	0.2912 (5)	0.6259 (3)	0.0385 (2)	0.0514 (13)
H26	0.2197	0.5985	0.0300	0.062*
C27	0.3874 (5)	0.5744 (3)	0.0397 (2)	0.0595 (15)
H27	0.3805	0.5118	0.0317	0.071*
C28	0.4935 (5)	0.6129 (3)	0.0526 (2)	0.0548 (13)
H28	0.5580	0.5766	0.0534	0.066*
C29	0.5046 (4)	0.7060 (3)	0.06431 (18)	0.0397 (10)
H29	0.5767	0.7323	0.0732	0.048*
C30	0.2498 (4)	0.8357 (3)	0.15572 (18)	0.0370 (10)
C35	0.1522 (5)	0.8182 (5)	0.1762 (3)	0.0771 (19)
H35	0.0811	0.8304	0.1544	0.093*
C34	0.1596 (8)	0.7825 (6)	0.2291 (4)	0.110 (3)
H34	0.0937	0.7719	0.2431	0.132*
C33	0.2635 (9)	0.7628 (5)	0.2606 (3)	0.102 (3)
H33	0.2683	0.7372	0.2957	0.123*
C32	0.3592 (7)	0.7803 (5)	0.2412 (2)	0.084 (2)
H32	0.4299	0.7672	0.2631	0.101*
C31	0.3528 (5)	0.8178 (4)	0.18866 (19)	0.0548 (14)
H31	0.4194	0.8308	0.1758	0.066*
C36	0.3509 (3)	1.0108 (3)	0.08862 (15)	0.0273 (8)
C37	0.3283 (4)	1.0558 (3)	0.13476 (17)	0.0393 (10)
H37	0.3061	1.0225	0.1633	0.047*
C38	0.3386 (4)	1.1501 (3)	0.13847 (19)	0.0435 (11)
H38	0.3236	1.1804	0.1697	0.052*
C39	0.3709 (3)	1.1997 (3)	0.09650 (17)	0.0341 (9)
C40	0.3922 (3)	1.1551 (3)	0.04987 (16)	0.0328 (9)
H40	0.4134	1.1888	0.0213	0.039*
C41	0.3820 (3)	1.0614 (3)	0.04573 (16)	0.0305 (9)
H41	0.3959	1.0315	0.0142	0.037*
C42	0.3831 (5)	1.3022 (3)	0.1012 (2)	0.0516 (13)
F6A	0.308 (2)	1.3467 (7)	0.0659 (11)	0.155 (13)	0.57 (3)
F5A	0.378 (3)	1.3360 (6)	0.1506 (5)	0.104 (7)	0.57 (3)
F4A	0.4828 (13)	1.3323 (8)	0.0936 (12)	0.112 (9)	0.57 (3)
N2	0.3391 (3)	0.9132 (2)	0.08403 (13)	0.0271 (7)
O2	0.5195 (2)	0.89607 (19)	0.06948 (12)	0.0364 (7)
S2	0.17800 (9)	0.78640 (9)	0.04611 (5)	0.0457 (3)
F4B	0.474 (2)	1.3253 (11)	0.1315 (15)	0.138 (16)	0.43 (3)
F5B	0.383 (3)	1.3413 (10)	0.0544 (8)	0.109 (12)	0.43 (3)
F6B	0.301 (2)	1.3415 (7)	0.1170 (15)	0.106 (10)	0.43 (3)
C43	0.6833 (6)	0.7489 (4)	0.2230 (2)	0.0640 (16)
H43	0.6441	0.8046	0.2200	0.077*
C44	0.7974 (6)	0.7450 (5)	0.2477 (2)	0.0703 (18)
H44	0.8358	0.7984	0.2613	0.084*
C45	0.8531 (6)	0.6628 (5)	0.2521 (2)	0.0708 (17)
H45	0.9297	0.6606	0.2689	0.085*
C46	0.7985 (5)	0.5832 (5)	0.2322 (2)	0.0657 (16)
H46	0.8378	0.5276	0.2355	0.079*
C47	0.6844 (5)	0.5861 (4)	0.2072 (2)	0.0599 (15)
C48	0.6283 (5)	0.6680 (4)	0.2028 (2)	0.0582 (14)
H48	0.5517	0.6699	0.1860	0.070*
C49	0.6264 (8)	0.4992 (5)	0.1851 (4)	0.112 (3)
H49A	0.6040	0.4655	0.2149	0.168*
H49B	0.6778	0.4625	0.1686	0.168*
H49C	0.5602	0.5137	0.1577	0.168*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.026 (2)	0.030 (2)	0.044 (2)	−0.0063 (17)	0.0144 (17)	−0.0091 (18)
C2	0.031 (2)	0.031 (2)	0.0272 (19)	0.0012 (17)	0.0082 (16)	0.0014 (16)
C3	0.036 (2)	0.027 (2)	0.0263 (19)	−0.0033 (17)	0.0092 (16)	0.0029 (16)
C4	0.044 (2)	0.031 (2)	0.027 (2)	0.0055 (19)	0.0029 (18)	−0.0022 (17)
C5	0.070 (3)	0.036 (3)	0.045 (3)	0.015 (3)	0.013 (2)	0.003 (2)
C6	0.098 (5)	0.030 (3)	0.055 (3)	−0.008 (3)	0.025 (3)	0.001 (2)
C7	0.068 (4)	0.038 (3)	0.059 (3)	−0.021 (3)	0.014 (3)	−0.002 (2)
C8	0.048 (3)	0.040 (3)	0.037 (2)	−0.012 (2)	0.008 (2)	0.006 (2)
C9	0.046 (3)	0.029 (2)	0.044 (2)	−0.0076 (19)	0.024 (2)	−0.0083 (19)
C10	0.067 (4)	0.060 (4)	0.079 (4)	−0.008 (3)	0.048 (3)	−0.013 (3)
C11	0.129 (7)	0.082 (5)	0.097 (6)	−0.012 (5)	0.088 (5)	−0.012 (4)
C12	0.163 (8)	0.078 (5)	0.060 (4)	−0.021 (6)	0.060 (5)	−0.006 (4)
C13	0.105 (5)	0.072 (4)	0.042 (3)	−0.015 (4)	0.011 (3)	0.005 (3)
C14	0.063 (3)	0.056 (3)	0.039 (3)	−0.011 (3)	0.014 (2)	0.004 (2)
C15	0.0273 (19)	0.028 (2)	0.032 (2)	−0.0021 (16)	0.0086 (16)	−0.0029 (16)
C16	0.055 (3)	0.034 (2)	0.040 (2)	−0.005 (2)	0.025 (2)	−0.0040 (19)
C17	0.057 (3)	0.032 (2)	0.049 (3)	−0.006 (2)	0.019 (2)	0.003 (2)
C18	0.033 (2)	0.029 (2)	0.048 (3)	−0.0012 (18)	0.0060 (19)	−0.0052 (19)
C19	0.029 (2)	0.035 (2)	0.035 (2)	−0.0013 (18)	0.0089 (17)	−0.0079 (18)
C20	0.030 (2)	0.034 (2)	0.0288 (19)	−0.0029 (18)	0.0076 (16)	0.0001 (17)
C21	0.061 (3)	0.031 (3)	0.069 (4)	0.000 (2)	0.011 (3)	−0.005 (2)
F1	0.080 (3)	0.0350 (17)	0.166 (4)	−0.0179 (17)	0.025 (3)	−0.019 (2)
F2	0.206 (5)	0.047 (2)	0.101 (3)	0.028 (3)	0.071 (3)	−0.014 (2)
F3	0.095 (3)	0.0451 (19)	0.144 (4)	0.0244 (19)	−0.032 (3)	−0.003 (2)
N1	0.0263 (17)	0.0288 (17)	0.0338 (17)	−0.0029 (14)	0.0126 (14)	−0.0020 (14)
O1	0.0307 (16)	0.0365 (17)	0.065 (2)	−0.0004 (13)	0.0208 (15)	0.0002 (15)
S1	0.0308 (6)	0.0465 (7)	0.0526 (7)	0.0113 (5)	0.0007 (5)	−0.0057 (6)
C22	0.026 (2)	0.028 (2)	0.043 (2)	0.0014 (17)	0.0153 (17)	−0.0001 (18)
C23	0.0272 (19)	0.030 (2)	0.0219 (17)	−0.0002 (16)	0.0078 (15)	−0.0006 (15)
C24	0.037 (2)	0.0222 (19)	0.0273 (19)	0.0016 (17)	0.0065 (16)	−0.0013 (15)
C25	0.044 (2)	0.034 (2)	0.029 (2)	−0.009 (2)	0.0050 (18)	−0.0046 (18)
C26	0.065 (3)	0.041 (3)	0.047 (3)	−0.022 (3)	0.007 (2)	−0.009 (2)
C27	0.092 (5)	0.030 (3)	0.058 (3)	−0.003 (3)	0.019 (3)	−0.009 (2)
C28	0.076 (4)	0.031 (3)	0.061 (3)	0.015 (3)	0.021 (3)	0.000 (2)
C29	0.046 (3)	0.036 (2)	0.039 (2)	0.006 (2)	0.014 (2)	−0.0002 (19)
C30	0.047 (3)	0.026 (2)	0.046 (2)	−0.0053 (19)	0.028 (2)	0.0014 (18)
C35	0.074 (4)	0.089 (5)	0.082 (4)	−0.026 (4)	0.049 (4)	−0.003 (4)
C34	0.146 (8)	0.101 (6)	0.113 (7)	−0.037 (6)	0.101 (6)	0.005 (5)
C33	0.215 (11)	0.047 (4)	0.067 (5)	−0.005 (5)	0.083 (6)	0.009 (3)
C32	0.133 (6)	0.077 (4)	0.047 (3)	0.038 (4)	0.028 (4)	0.017 (3)
C31	0.071 (4)	0.060 (3)	0.037 (3)	0.016 (3)	0.021 (2)	0.013 (2)
C36	0.0263 (19)	0.027 (2)	0.0291 (19)	0.0026 (16)	0.0066 (15)	0.0038 (16)
C37	0.054 (3)	0.034 (2)	0.036 (2)	0.003 (2)	0.023 (2)	0.0026 (18)
C38	0.060 (3)	0.033 (2)	0.043 (2)	0.004 (2)	0.022 (2)	−0.010 (2)
C39	0.035 (2)	0.026 (2)	0.042 (2)	0.0013 (18)	0.0074 (18)	−0.0025 (18)
C40	0.034 (2)	0.032 (2)	0.034 (2)	0.0029 (18)	0.0098 (17)	0.0094 (17)
C41	0.034 (2)	0.031 (2)	0.0288 (19)	0.0031 (17)	0.0105 (17)	−0.0001 (16)
C42	0.063 (4)	0.035 (3)	0.057 (3)	−0.005 (3)	0.010 (3)	−0.003 (2)
F6A	0.166 (17)	0.036 (4)	0.20 (2)	0.001 (9)	−0.125 (16)	0.018 (11)
F5A	0.20 (2)	0.038 (4)	0.084 (7)	−0.002 (8)	0.062 (10)	−0.020 (4)
F4A	0.096 (12)	0.053 (6)	0.21 (2)	−0.034 (7)	0.078 (15)	−0.037 (11)
N2	0.0268 (16)	0.0257 (16)	0.0306 (17)	0.0005 (14)	0.0098 (13)	0.0017 (13)
O2	0.0318 (15)	0.0311 (15)	0.0500 (18)	−0.0044 (13)	0.0170 (13)	−0.0068 (13)
S2	0.0273 (5)	0.0535 (7)	0.0526 (7)	−0.0094 (5)	−0.0015 (5)	−0.0055 (6)
F4B	0.14 (2)	0.048 (6)	0.18 (3)	−0.020 (11)	−0.085 (19)	−0.028 (14)
F5B	0.22 (3)	0.029 (5)	0.086 (12)	−0.007 (13)	0.060 (17)	0.007 (6)
F6B	0.117 (15)	0.037 (5)	0.18 (3)	0.028 (7)	0.081 (16)	−0.016 (11)
C43	0.087 (4)	0.069 (4)	0.040 (3)	0.004 (3)	0.021 (3)	0.016 (3)
C44	0.090 (5)	0.080 (5)	0.041 (3)	−0.032 (4)	0.015 (3)	0.002 (3)
C45	0.066 (4)	0.098 (5)	0.048 (3)	−0.010 (4)	0.008 (3)	0.008 (3)
C46	0.072 (4)	0.079 (4)	0.048 (3)	0.019 (3)	0.016 (3)	0.017 (3)
C47	0.072 (4)	0.061 (4)	0.048 (3)	−0.008 (3)	0.013 (3)	0.014 (3)
C48	0.056 (3)	0.072 (4)	0.046 (3)	0.004 (3)	0.007 (2)	0.018 (3)
C49	0.131 (7)	0.080 (5)	0.124 (7)	−0.012 (5)	0.026 (6)	0.010 (5)

Geometric parameters (Å, º)

C1—H1	0.9800	C25—C26	1.407 (6)
C1—C9	1.514 (6)	C25—S2	1.743 (5)
C1—N1	1.456 (5)	C26—H26	0.9300
C1—S1	1.811 (4)	C26—C27	1.367 (7)
C2—C3	1.501 (5)	C27—H27	0.9300
C2—N1	1.375 (5)	C27—C28	1.367 (7)
C2—O1	1.215 (4)	C28—H28	0.9300
C3—C4	1.379 (5)	C28—C29	1.384 (6)
C3—C8	1.395 (6)	C29—H29	0.9300
C4—C5	1.394 (6)	C30—C35	1.379 (6)
C4—S1	1.744 (4)	C30—C31	1.362 (6)
C5—H5	0.9300	C35—H35	0.9300
C5—C6	1.369 (7)	C35—C34	1.386 (9)
C6—H6	0.9300	C34—H34	0.9300
C6—C7	1.365 (7)	C34—C33	1.362 (10)
C7—H7	0.9300	C33—H33	0.9300
C7—C8	1.384 (6)	C33—C32	1.344 (10)
C8—H8	0.9300	C32—H32	0.9300
C9—C10	1.383 (6)	C32—C31	1.389 (7)
C9—C14	1.369 (6)	C31—H31	0.9300
C10—H10	0.9300	C36—C37	1.378 (5)
C10—C11	1.390 (8)	C36—C41	1.391 (5)
C11—H11	0.9300	C36—N2	1.425 (5)
C11—C12	1.365 (10)	C37—H37	0.9300
C12—H12	0.9300	C37—C38	1.376 (6)
C12—C13	1.353 (9)	C38—H38	0.9300
C13—H13	0.9300	C38—C39	1.371 (6)
C13—C14	1.388 (7)	C39—C40	1.380 (5)
C14—H14	0.9300	C39—C42	1.497 (6)
C15—C16	1.390 (5)	C40—H40	0.9300
C15—C20	1.383 (5)	C40—C41	1.368 (5)
C15—N1	1.430 (5)	C41—H41	0.9300
C16—H16	0.9300	C42—F6A	1.292 (9)
C16—C17	1.373 (6)	C42—F5A	1.321 (9)
C17—H17	0.9300	C42—F4A	1.316 (10)
C17—C18	1.372 (6)	C42—F4B	1.239 (15)
C18—C19	1.379 (6)	C42—F5B	1.283 (15)
C18—C21	1.501 (6)	C42—F6B	1.262 (12)
C19—H19	0.9300	C43—H43	0.9300
C19—C20	1.375 (5)	C43—C44	1.383 (9)
C20—H20	0.9300	C43—C48	1.390 (8)
C21—F1	1.321 (6)	C44—H44	0.9300
C21—F2	1.301 (6)	C44—C45	1.360 (9)
C21—F3	1.318 (6)	C45—H45	0.9300
C22—H22	0.9800	C45—C46	1.371 (9)
C22—C30	1.503 (5)	C46—H46	0.9300
C22—N2	1.463 (5)	C46—C47	1.385 (8)
C22—S2	1.816 (4)	C47—C48	1.358 (8)
C23—C24	1.493 (5)	C47—C49	1.491 (9)
C23—N2	1.370 (5)	C48—H48	0.9300
C23—O2	1.225 (4)	C49—H49A	0.9600
C24—C25	1.386 (5)	C49—H49B	0.9600
C24—C29	1.388 (6)	C49—H49C	0.9600
C9—C1—H1	106.0	C25—C26—H26	120.3
C9—C1—S1	112.6 (3)	C27—C26—C25	119.4 (5)
N1—C1—H1	106.0	C27—C26—H26	120.3
N1—C1—C9	114.7 (3)	C26—C27—H27	119.3
N1—C1—S1	110.9 (3)	C28—C27—C26	121.4 (5)
S1—C1—H1	106.0	C28—C27—H27	119.3
N1—C2—C3	117.4 (3)	C27—C28—H28	120.2
O1—C2—C3	120.6 (4)	C27—C28—C29	119.6 (5)
O1—C2—N1	122.0 (4)	C29—C28—H28	120.2
C4—C3—C2	123.8 (4)	C24—C29—H29	119.8
C4—C3—C8	119.4 (4)	C28—C29—C24	120.5 (5)
C8—C3—C2	116.6 (4)	C28—C29—H29	119.8
C3—C4—C5	119.4 (4)	C35—C30—C22	117.6 (5)
C3—C4—S1	121.4 (3)	C31—C30—C22	123.7 (4)
C5—C4—S1	119.1 (4)	C31—C30—C35	118.7 (5)
C4—C5—H5	119.8	C30—C35—H35	119.9
C6—C5—C4	120.5 (5)	C30—C35—C34	120.2 (7)
C6—C5—H5	119.8	C34—C35—H35	119.9
C5—C6—H6	119.7	C35—C34—H34	120.0
C7—C6—C5	120.7 (5)	C33—C34—C35	119.9 (6)
C7—C6—H6	119.7	C33—C34—H34	120.0
C6—C7—H7	120.2	C34—C33—H33	119.8
C6—C7—C8	119.7 (5)	C32—C33—C34	120.3 (6)
C8—C7—H7	120.2	C32—C33—H33	119.8
C3—C8—H8	119.8	C33—C32—H32	119.9
C7—C8—C3	120.4 (5)	C33—C32—C31	120.2 (7)
C7—C8—H8	119.8	C31—C32—H32	119.9
C10—C9—C1	117.9 (4)	C30—C31—C32	120.6 (5)
C14—C9—C1	124.1 (4)	C30—C31—H31	119.7
C14—C9—C10	118.0 (5)	C32—C31—H31	119.7
C9—C10—H10	119.9	C37—C36—C41	119.6 (4)
C9—C10—C11	120.1 (6)	C37—C36—N2	120.3 (3)
C11—C10—H10	119.9	C41—C36—N2	120.1 (3)
C10—C11—H11	119.8	C36—C37—H37	120.1
C12—C11—C10	120.4 (6)	C38—C37—C36	119.8 (4)
C12—C11—H11	119.8	C38—C37—H37	120.1
C11—C12—H12	120.0	C37—C38—H38	119.8
C13—C12—C11	120.1 (6)	C39—C38—C37	120.5 (4)
C13—C12—H12	120.0	C39—C38—H38	119.8
C12—C13—H13	120.2	C38—C39—C40	120.0 (4)
C12—C13—C14	119.6 (6)	C38—C39—C42	120.1 (4)
C14—C13—H13	120.2	C40—C39—C42	120.0 (4)
C9—C14—C13	121.7 (5)	C39—C40—H40	120.0
C9—C14—H14	119.2	C41—C40—C39	120.0 (4)
C13—C14—H14	119.2	C41—C40—H40	120.0
C16—C15—N1	119.5 (3)	C36—C41—H41	119.9
C20—C15—C16	119.4 (4)	C40—C41—C36	120.1 (4)
C20—C15—N1	121.1 (3)	C40—C41—H41	119.9
C15—C16—H16	119.9	F6A—C42—C39	113.6 (6)
C17—C16—C15	120.2 (4)	F6A—C42—F5A	106.2 (10)
C17—C16—H16	119.9	F6A—C42—F4A	105.4 (10)
C16—C17—H17	120.0	F5A—C42—C39	114.8 (6)
C18—C17—C16	120.1 (4)	F4A—C42—C39	113.4 (7)
C18—C17—H17	120.0	F4A—C42—F5A	102.3 (8)
C17—C18—C19	120.1 (4)	F4B—C42—C39	112.2 (9)
C17—C18—C21	119.1 (4)	F4B—C42—F5B	105.4 (14)
C19—C18—C21	120.7 (4)	F4B—C42—F6B	109.8 (13)
C18—C19—H19	119.9	F5B—C42—C39	112.8 (8)
C20—C19—C18	120.2 (4)	F6B—C42—C39	113.8 (7)
C20—C19—H19	119.9	F6B—C42—F5B	102.2 (11)
C15—C20—H20	120.0	C23—N2—C22	122.8 (3)
C19—C20—C15	120.0 (4)	C23—N2—C36	119.6 (3)
C19—C20—H20	120.0	C36—N2—C22	117.3 (3)
F1—C21—C18	112.5 (4)	C25—S2—C22	97.41 (18)
F2—C21—C18	114.1 (4)	C44—C43—H43	120.6
F2—C21—F1	106.3 (5)	C44—C43—C48	118.7 (6)
F2—C21—F3	106.2 (5)	C48—C43—H43	120.6
F3—C21—C18	112.5 (4)	C43—C44—H44	120.1
F3—C21—F1	104.6 (5)	C45—C44—C43	119.9 (6)
C2—N1—C1	122.2 (3)	C45—C44—H44	120.1
C2—N1—C15	119.6 (3)	C44—C45—H45	119.4
C15—N1—C1	117.5 (3)	C44—C45—C46	121.2 (6)
C4—S1—C1	97.37 (19)	C46—C45—H45	119.4
C30—C22—H22	106.5	C45—C46—H46	120.2
C30—C22—S2	112.0 (3)	C45—C46—C47	119.6 (6)
N2—C22—H22	106.5	C47—C46—H46	120.2
N2—C22—C30	114.5 (3)	C46—C47—C49	119.0 (6)
N2—C22—S2	110.3 (3)	C48—C47—C46	119.4 (6)
S2—C22—H22	106.5	C48—C47—C49	121.6 (6)
N2—C23—C24	118.2 (3)	C43—C48—H48	119.4
O2—C23—C24	120.2 (3)	C47—C48—C43	121.2 (6)
O2—C23—N2	121.6 (3)	C47—C48—H48	119.4
C25—C24—C23	123.3 (4)	C47—C49—H49A	109.5
C25—C24—C29	119.4 (4)	C47—C49—H49B	109.5
C29—C24—C23	117.2 (4)	C47—C49—H49C	109.5
C24—C25—C26	119.6 (4)	H49A—C49—H49B	109.5
C24—C25—S2	121.4 (3)	H49A—C49—H49C	109.5
C26—C25—S2	118.9 (4)	H49B—C49—H49C	109.5
C1—C9—C10—C11	178.5 (5)	C24—C25—C26—C27	0.1 (7)
C1—C9—C14—C13	−178.7 (5)	C24—C25—S2—C22	−31.4 (4)
C2—C3—C4—C5	−171.8 (4)	C25—C24—C29—C28	0.8 (6)
C2—C3—C4—S1	5.2 (5)	C25—C26—C27—C28	0.5 (8)
C2—C3—C8—C7	173.2 (4)	C26—C25—S2—C22	151.0 (4)
C3—C2—N1—C1	−12.6 (5)	C26—C27—C28—C29	−0.4 (8)
C3—C2—N1—C15	177.5 (3)	C27—C28—C29—C24	−0.3 (7)
C3—C4—C5—C6	−1.5 (7)	C29—C24—C25—C26	−0.7 (6)
C3—C4—S1—C1	28.5 (4)	C29—C24—C25—S2	−178.3 (3)
C4—C3—C8—C7	−1.3 (6)	C30—C22—N2—C23	77.0 (4)
C4—C5—C6—C7	−0.3 (8)	C30—C22—N2—C36	−96.8 (4)
C5—C4—S1—C1	−154.5 (4)	C30—C22—S2—C25	−75.1 (3)
C5—C6—C7—C8	1.3 (8)	C30—C35—C34—C33	−1.4 (12)
C6—C7—C8—C3	−0.5 (7)	C35—C30—C31—C32	1.7 (8)
C8—C3—C4—C5	2.2 (6)	C35—C34—C33—C32	1.8 (13)
C8—C3—C4—S1	179.3 (3)	C34—C33—C32—C31	−0.5 (11)
C9—C1—N1—C2	−77.0 (5)	C33—C32—C31—C30	−1.3 (9)
C9—C1—N1—C15	93.1 (4)	C31—C30—C35—C34	−0.4 (9)
C9—C1—S1—C4	76.4 (3)	C36—C37—C38—C39	0.2 (7)
C9—C10—C11—C12	0.6 (10)	C37—C36—C41—C40	1.3 (6)
C10—C9—C14—C13	−0.6 (8)	C37—C36—N2—C22	46.0 (5)
C10—C11—C12—C13	−1.2 (12)	C37—C36—N2—C23	−128.0 (4)
C11—C12—C13—C14	0.9 (11)	C37—C38—C39—C40	0.6 (7)
C12—C13—C14—C9	0.0 (9)	C37—C38—C39—C42	−179.3 (5)
C14—C9—C10—C11	0.3 (8)	C38—C39—C40—C41	−0.5 (6)
C15—C16—C17—C18	−0.1 (7)	C38—C39—C42—F6A	−113 (2)
C16—C15—C20—C19	−1.9 (6)	C38—C39—C42—F5A	9.7 (16)
C16—C15—N1—C1	−41.8 (5)	C38—C39—C42—F4A	126.8 (15)
C16—C15—N1—C2	128.6 (4)	C38—C39—C42—F4B	79 (2)
C16—C17—C18—C19	−1.8 (7)	C38—C39—C42—F5B	−162.5 (19)
C16—C17—C18—C21	175.8 (5)	C38—C39—C42—F6B	−47 (2)
C17—C18—C19—C20	1.8 (6)	C39—C40—C41—C36	−0.4 (6)
C17—C18—C21—F1	51.4 (6)	C40—C39—C42—F6A	67 (2)
C17—C18—C21—F2	172.5 (5)	C40—C39—C42—F5A	−170.3 (15)
C17—C18—C21—F3	−66.5 (6)	C40—C39—C42—F4A	−53.1 (15)
C18—C19—C20—C15	0.0 (6)	C40—C39—C42—F4B	−101 (2)
C19—C18—C21—F1	−131.0 (5)	C40—C39—C42—F5B	17.5 (19)
C19—C18—C21—F2	−9.9 (7)	C40—C39—C42—F6B	133 (2)
C19—C18—C21—F3	111.2 (5)	C41—C36—C37—C38	−1.2 (7)
C20—C15—C16—C17	1.9 (7)	C41—C36—N2—C22	−132.0 (4)
C20—C15—N1—C1	136.4 (4)	C41—C36—N2—C23	54.0 (5)
C20—C15—N1—C2	−53.2 (5)	C42—C39—C40—C41	179.4 (4)
C21—C18—C19—C20	−175.7 (4)	N2—C22—C30—C35	163.7 (4)
N1—C1—C9—C10	−164.6 (4)	N2—C22—C30—C31	−17.2 (6)
N1—C1—C9—C14	13.5 (6)	N2—C22—S2—C25	53.7 (3)
N1—C1—S1—C4	−53.7 (3)	N2—C23—C24—C25	18.0 (5)
N1—C2—C3—C4	−19.7 (6)	N2—C23—C24—C29	−165.2 (3)
N1—C2—C3—C8	166.1 (3)	N2—C36—C37—C38	−179.2 (4)
N1—C15—C16—C17	−179.9 (4)	N2—C36—C41—C40	179.3 (4)
N1—C15—C20—C19	179.9 (4)	O2—C23—C24—C25	−161.5 (4)
O1—C2—C3—C4	160.7 (4)	O2—C23—C24—C29	15.4 (5)
O1—C2—C3—C8	−13.5 (6)	O2—C23—N2—C22	−168.8 (4)
O1—C2—N1—C1	167.0 (4)	O2—C23—N2—C36	4.9 (5)
O1—C2—N1—C15	−2.9 (6)	S2—C22—C30—C35	−69.8 (5)
S1—C1—C9—C10	67.3 (5)	S2—C22—C30—C31	109.3 (4)
S1—C1—C9—C14	−114.6 (4)	S2—C22—N2—C23	−50.4 (4)
S1—C1—N1—C2	51.9 (4)	S2—C22—N2—C36	135.8 (3)
S1—C1—N1—C15	−138.0 (3)	S2—C25—C26—C27	177.7 (4)
S1—C4—C5—C6	−178.6 (4)	C43—C44—C45—C46	0.4 (9)
C22—C30—C35—C34	178.6 (6)	C44—C43—C48—C47	0.3 (8)
C22—C30—C31—C32	−177.3 (5)	C44—C45—C46—C47	−0.1 (9)
C23—C24—C25—C26	176.1 (4)	C45—C46—C47—C48	−0.1 (8)
C23—C24—C25—S2	−1.5 (5)	C45—C46—C47—C49	179.3 (6)
C23—C24—C29—C28	−176.2 (4)	C46—C47—C48—C43	0.0 (8)
C24—C23—N2—C22	11.7 (5)	C48—C43—C44—C45	−0.5 (8)
C24—C23—N2—C36	−174.6 (3)	C49—C47—C48—C43	−179.4 (6)

Hydrogen-bond geometry (Å, º)

Cg(X) = center of gravity of ring (X); D—H···CgX = angle of the D—H bond with the π plane

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.98	2.25	3.2053 (7)	165
C22—H22···O1^i	0.98	2.34	3.3140 (7)	171
C17—H17···Cg9	0.93	2.79	3.5916 (7)	145
C38—H38···Cg9^ii	0.93	2.78	3.6009 (7)	147

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

(III) 3-(3-Bromophenyl)-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one toluene hemisolvate

Crystal data

2C20H14BrNOS·C7H8	Dx = 1.485 Mg m^−3
Mr = 884.72	Melting point = 358–359 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.736 (2) Å	Cell parameters from 3326 reflections
b = 9.3530 (15) Å	θ = 2.5–25.0°
c = 27.259 (4) Å	µ = 2.20 mm^−1
β = 99.560 (3)°	T = 298 K
V = 3956.2 (10) Å^3	Block, colorless
Z = 4	0.21 × 0.17 × 0.10 mm
F(000) = 1800

Data collection

Bruker CCD area-detector diffractometer	2424 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.064
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.3°, θmin = 2.5°
Tmin = 0.103, Tmax = 0.901	h = −20→20
18289 measured reflections	k = −12→12
4903 independent reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.79	(Δ/σ)max < 0.001
4903 reflections	Δρmax = 0.73 e Å^−3
266 parameters	Δρmin = −0.71 e Å^−3
186 restraints

Special details

Experimental. Absorption correction: SADABS was used for absorption correction. R(int) was 0.2680 before and 0.0355 after correction. The Ratio of minimum to maximum transmission is 0.1027. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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	Occ. (<1)
Br1	0.45074 (3)	0.27453 (5)	0.01191 (2)	0.0874 (2)
C1	0.3189 (2)	−0.2500 (3)	−0.12554 (12)	0.0471 (8)
H1	0.2798	−0.2262	−0.1023	0.057*
C2	0.4549 (2)	−0.1391 (3)	−0.14162 (11)	0.0479 (8)
C3	0.4821 (2)	−0.2827 (3)	−0.15744 (12)	0.0506 (8)
C4	0.4518 (2)	−0.4113 (3)	−0.14088 (11)	0.0540 (9)
C5	0.4858 (3)	−0.5405 (4)	−0.15463 (15)	0.0736 (12)
H5	0.4662	−0.6269	−0.1438	0.088*
C6	0.5487 (3)	−0.5386 (5)	−0.18431 (16)	0.0840 (14)
H6	0.5723	−0.6246	−0.1927	0.101*
C7	0.5774 (3)	−0.4129 (5)	−0.20176 (15)	0.0766 (12)
H7	0.6178	−0.4141	−0.2231	0.092*
C8	0.5453 (2)	−0.2859 (4)	−0.18817 (13)	0.0613 (9)
H8	0.5657	−0.2006	−0.1994	0.074*
C9	0.2622 (2)	−0.2733 (3)	−0.17542 (11)	0.0441 (7)
C10	0.2728 (2)	−0.1978 (4)	−0.21777 (12)	0.0551 (9)
H10	0.3176	−0.1322	−0.2164	0.066*
C11	0.2169 (3)	−0.2193 (4)	−0.26239 (14)	0.0650 (10)
H11	0.2250	−0.1686	−0.2906	0.078*
C12	0.1505 (3)	−0.3137 (4)	−0.26511 (14)	0.0653 (10)
H12	0.1139	−0.3288	−0.2951	0.078*
C13	0.1381 (2)	−0.3865 (3)	−0.22331 (15)	0.0646 (10)
H13	0.0915	−0.4485	−0.2247	0.078*
C14	0.1942 (2)	−0.3683 (3)	−0.17905 (13)	0.0565 (9)
H14	0.1861	−0.4209	−0.1512	0.068*
C15	0.3547 (2)	0.0010 (3)	−0.10271 (10)	0.0444 (7)
C16	0.2748 (2)	0.0582 (4)	−0.11998 (12)	0.0605 (9)
H16	0.2388	0.0144	−0.1462	0.073*
C17	0.2477 (3)	0.1802 (4)	−0.09865 (14)	0.0684 (11)
H17	0.1940	0.2192	−0.1107	0.082*
C18	0.3005 (3)	0.2443 (3)	−0.05941 (14)	0.0602 (10)
H18	0.2825	0.3262	−0.0447	0.072*
C19	0.3790 (2)	0.1866 (3)	−0.04242 (12)	0.0519 (8)
C20	0.4081 (2)	0.0654 (3)	−0.06351 (11)	0.0498 (8)
H20	0.4624	0.0280	−0.0516	0.060*
N1	0.37987 (17)	−0.1309 (2)	−0.12306 (9)	0.0436 (6)
O1	0.49900 (16)	−0.0328 (3)	−0.14536 (9)	0.0642 (7)
S1	0.37419 (7)	−0.41236 (9)	−0.10170 (3)	0.0632 (3)
C21	0.3612 (7)	−0.228 (2)	0.0506 (4)	0.146 (15)	0.5
H21A	0.4040	−0.2957	0.0440	0.219*	0.5
H21B	0.3479	−0.2455	0.0832	0.219*	0.5
H21C	0.3831	−0.1330	0.0489	0.219*	0.5
C22	0.2809 (6)	−0.2458 (12)	0.0125 (3)	0.135 (7)	0.5
C23	0.2341 (8)	−0.1264 (10)	−0.0081 (4)	0.123 (8)	0.5
H23	0.2537	−0.0351	0.0015	0.147*	0.5
C24	0.1585 (7)	−0.1422 (11)	−0.0426 (4)	0.145 (9)	0.5
H24	0.1283	−0.0618	−0.0558	0.174*	0.5
C25	0.1282 (5)	−0.2785 (13)	−0.0573 (3)	0.160 (14)	0.5
H25	0.0779	−0.2893	−0.0803	0.192*	0.5
C26	0.1743 (6)	−0.3985 (10)	−0.0374 (3)	0.086 (3)	0.5
H26	0.1546	−0.4896	−0.0470	0.103*	0.5
C27	0.2498 (6)	−0.3820 (10)	−0.0028 (3)	0.105 (6)	0.5
H27	0.2800	−0.4626	0.0102	0.125*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0933 (4)	0.0782 (3)	0.0831 (3)	0.0078 (2)	−0.0077 (2)	−0.0405 (2)
C1	0.054 (2)	0.0439 (17)	0.0465 (18)	−0.0039 (14)	0.0166 (15)	−0.0027 (13)
C2	0.055 (2)	0.0477 (18)	0.0418 (17)	0.0015 (16)	0.0104 (15)	−0.0051 (13)
C3	0.050 (2)	0.0543 (18)	0.0451 (18)	0.0068 (15)	−0.0007 (15)	−0.0095 (14)
C4	0.058 (2)	0.0494 (18)	0.0483 (18)	0.0078 (16)	−0.0085 (15)	−0.0059 (14)
C5	0.077 (3)	0.050 (2)	0.083 (3)	0.0155 (19)	−0.017 (2)	−0.0109 (18)
C6	0.076 (3)	0.082 (3)	0.086 (3)	0.043 (3)	−0.010 (2)	−0.031 (2)
C7	0.063 (3)	0.099 (3)	0.064 (2)	0.026 (2)	−0.0003 (19)	−0.021 (2)
C8	0.050 (2)	0.080 (2)	0.053 (2)	0.0138 (19)	0.0033 (17)	−0.0137 (17)
C9	0.050 (2)	0.0359 (14)	0.0486 (18)	0.0026 (14)	0.0144 (15)	−0.0056 (12)
C10	0.056 (2)	0.0550 (19)	0.055 (2)	−0.0074 (16)	0.0098 (17)	−0.0003 (15)
C11	0.070 (3)	0.070 (2)	0.054 (2)	0.003 (2)	0.0094 (19)	−0.0010 (17)
C12	0.067 (3)	0.056 (2)	0.067 (2)	0.009 (2)	−0.0057 (19)	−0.0172 (18)
C13	0.056 (3)	0.0447 (18)	0.091 (3)	−0.0053 (17)	0.004 (2)	−0.0168 (19)
C14	0.058 (2)	0.0423 (17)	0.070 (2)	−0.0031 (16)	0.0157 (18)	−0.0022 (15)
C15	0.056 (2)	0.0394 (15)	0.0404 (16)	−0.0004 (14)	0.0144 (15)	−0.0006 (12)
C16	0.062 (2)	0.062 (2)	0.054 (2)	0.0100 (18)	−0.0033 (17)	−0.0125 (16)
C17	0.065 (3)	0.066 (2)	0.069 (2)	0.024 (2)	−0.0027 (19)	−0.0134 (19)
C18	0.075 (3)	0.0435 (18)	0.064 (2)	0.0102 (17)	0.015 (2)	−0.0054 (15)
C19	0.063 (2)	0.0442 (16)	0.0478 (18)	0.0006 (16)	0.0085 (16)	−0.0081 (14)
C20	0.054 (2)	0.0458 (17)	0.0496 (18)	0.0016 (15)	0.0098 (15)	−0.0043 (14)
N1	0.0467 (17)	0.0403 (13)	0.0457 (14)	−0.0042 (11)	0.0132 (12)	−0.0079 (11)
O1	0.0639 (17)	0.0552 (14)	0.0797 (16)	−0.0133 (12)	0.0304 (13)	−0.0105 (12)
S1	0.0802 (7)	0.0477 (5)	0.0597 (5)	−0.0038 (4)	0.0061 (5)	0.0101 (4)
C21	0.062 (11)	0.31 (5)	0.074 (10)	−0.006 (17)	0.029 (9)	0.029 (15)
C22	0.131 (17)	0.196 (15)	0.104 (13)	−0.034 (15)	0.096 (13)	−0.052 (12)
C23	0.147 (16)	0.109 (14)	0.143 (13)	−0.016 (13)	0.118 (12)	−0.049 (13)
C24	0.19 (2)	0.097 (10)	0.18 (2)	0.028 (11)	0.128 (17)	0.041 (11)
C25	0.120 (17)	0.26 (4)	0.123 (15)	−0.085 (18)	0.076 (12)	−0.080 (18)
C26	0.088 (8)	0.094 (7)	0.084 (7)	0.004 (6)	0.040 (6)	0.014 (6)
C27	0.174 (18)	0.056 (8)	0.106 (10)	0.002 (9)	0.088 (11)	0.002 (6)

Geometric parameters (Å, º)

Br1—C19	1.895 (3)	C13—C14	1.383 (5)
C1—H1	0.9800	C14—H14	0.9300
C1—C9	1.513 (5)	C15—C16	1.376 (4)
C1—N1	1.464 (4)	C15—C20	1.382 (4)
C1—S1	1.815 (3)	C15—N1	1.435 (4)
C2—C3	1.494 (4)	C16—H16	0.9300
C2—N1	1.362 (4)	C16—C17	1.380 (5)
C2—O1	1.227 (4)	C17—H17	0.9300
C3—C4	1.396 (5)	C17—C18	1.377 (5)
C3—C8	1.404 (5)	C18—H18	0.9300
C4—C5	1.398 (5)	C18—C19	1.357 (5)
C4—S1	1.750 (4)	C19—C20	1.384 (4)
C5—H5	0.9300	C20—H20	0.9300
C5—C6	1.379 (6)	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C6—C7	1.372 (6)	C21—H21C	0.9600
C7—H7	0.9297	C21—C22	1.5069
C7—C8	1.365 (5)	C22—C23	1.4022
C8—H8	0.9300	C22—C27	1.4024
C9—C10	1.387 (5)	C23—H23	0.9300
C9—C14	1.382 (4)	C23—C24	1.3963
C10—H10	0.9300	C24—H24	0.9300
C10—C11	1.392 (5)	C24—C25	1.3964
C11—H11	0.9300	C25—H25	0.9300
C11—C12	1.361 (5)	C25—C26	1.3966
C12—H12	0.9300	C26—H26	0.9300
C12—C13	1.369 (5)	C26—C27	1.3963
C13—H13	0.9300	C27—H27	0.9300
C9—C1—H1	105.9	C16—C15—N1	119.8 (3)
C9—C1—S1	112.2 (2)	C20—C15—N1	120.1 (3)
N1—C1—H1	105.9	C15—C16—H16	119.8
N1—C1—C9	115.8 (2)	C15—C16—C17	120.4 (3)
N1—C1—S1	110.4 (2)	C17—C16—H16	119.8
S1—C1—H1	105.9	C16—C17—H17	120.0
N1—C2—C3	117.7 (3)	C18—C17—C16	119.9 (3)
O1—C2—C3	120.8 (3)	C18—C17—H17	120.0
O1—C2—N1	121.5 (3)	C17—C18—H18	120.4
C4—C3—C2	123.5 (3)	C19—C18—C17	119.3 (3)
C4—C3—C8	119.3 (3)	C19—C18—H18	120.4
C8—C3—C2	117.1 (3)	C18—C19—Br1	119.0 (2)
C3—C4—C5	119.4 (4)	C18—C19—C20	122.0 (3)
C3—C4—S1	120.8 (2)	C20—C19—Br1	119.0 (3)
C5—C4—S1	119.7 (3)	C15—C20—C19	118.5 (3)
C4—C5—H5	120.3	C15—C20—H20	120.8
C6—C5—C4	119.4 (4)	C19—C20—H20	120.8
C6—C5—H5	120.3	C2—N1—C1	122.8 (2)
C5—C6—H6	119.2	C2—N1—C15	120.2 (2)
C7—C6—C5	121.6 (4)	C15—N1—C1	116.9 (2)
C7—C6—H6	119.2	C4—S1—C1	96.77 (15)
C6—C7—H7	120.3	H21A—C21—H21B	109.5
C8—C7—C6	119.6 (4)	H21A—C21—H21C	109.5
C8—C7—H7	120.1	H21B—C21—H21C	109.5
C3—C8—H8	119.6	C22—C21—H21A	109.5
C7—C8—C3	120.7 (4)	C22—C21—H21B	109.5
C7—C8—H8	119.6	C22—C21—H21C	109.5
C10—C9—C1	122.7 (3)	C23—C22—C21	121.0
C14—C9—C1	119.4 (3)	C23—C22—C27	118.1
C14—C9—C10	117.8 (3)	C27—C22—C21	120.9
C9—C10—H10	119.7	C22—C23—H23	119.4
C9—C10—C11	120.5 (3)	C24—C23—C22	121.1
C11—C10—H10	119.7	C24—C23—H23	119.4
C10—C11—H11	119.7	C23—C24—H24	119.9
C12—C11—C10	120.6 (4)	C23—C24—C25	120.1
C12—C11—H11	119.7	C25—C24—H24	119.9
C11—C12—H12	120.3	C24—C25—H25	120.3
C11—C12—C13	119.5 (3)	C24—C25—C26	119.4
C13—C12—H12	120.3	C26—C25—H25	120.3
C12—C13—H13	119.8	C25—C26—H26	119.9
C12—C13—C14	120.4 (3)	C27—C26—C25	120.1
C14—C13—H13	119.8	C27—C26—H26	119.9
C9—C14—C13	121.1 (3)	C22—C27—H27	119.5
C9—C14—H14	119.4	C26—C27—C22	121.1
C13—C14—H14	119.4	C26—C27—H27	119.5
C16—C15—C20	119.9 (3)
Br1—C19—C20—C15	179.2 (2)	C17—C18—C19—Br1	−179.5 (3)
C1—C9—C10—C11	−177.6 (3)	C17—C18—C19—C20	0.4 (6)
C1—C9—C14—C13	176.3 (3)	C18—C19—C20—C15	−0.7 (5)
C2—C3—C4—C5	−175.0 (3)	C20—C15—C16—C17	0.5 (5)
C2—C3—C4—S1	3.0 (5)	C20—C15—N1—C1	125.6 (3)
C2—C3—C8—C7	176.0 (3)	C20—C15—N1—C2	−58.2 (4)
C3—C2—N1—C1	−10.2 (4)	N1—C1—C9—C10	6.7 (4)
C3—C2—N1—C15	173.8 (3)	N1—C1—C9—C14	−170.0 (3)
C3—C4—C5—C6	0.0 (5)	N1—C1—S1—C4	−54.9 (2)
C3—C4—S1—C1	31.4 (3)	N1—C2—C3—C4	−20.5 (5)
C4—C3—C8—C7	−0.2 (5)	N1—C2—C3—C8	163.5 (3)
C4—C5—C6—C7	−1.6 (6)	N1—C15—C16—C17	176.0 (3)
C5—C4—S1—C1	−150.5 (3)	N1—C15—C20—C19	−175.2 (3)
C5—C6—C7—C8	2.3 (6)	O1—C2—C3—C4	159.5 (3)
C6—C7—C8—C3	−1.4 (6)	O1—C2—C3—C8	−16.5 (5)
C8—C3—C4—C5	0.9 (5)	O1—C2—N1—C1	169.7 (3)
C8—C3—C4—S1	179.0 (2)	O1—C2—N1—C15	−6.2 (4)
C9—C1—N1—C2	−77.8 (4)	S1—C1—C9—C10	−121.2 (3)
C9—C1—N1—C15	98.2 (3)	S1—C1—C9—C14	62.0 (4)
C9—C1—S1—C4	75.8 (3)	S1—C1—N1—C2	51.0 (3)
C9—C10—C11—C12	0.6 (5)	S1—C1—N1—C15	−132.9 (2)
C10—C9—C14—C13	−0.6 (5)	S1—C4—C5—C6	−178.1 (3)
C10—C11—C12—C13	1.0 (6)	C21—C22—C23—C24	−178.5
C11—C12—C13—C14	−2.4 (5)	C21—C22—C27—C26	178.5
C12—C13—C14—C9	2.2 (5)	C22—C23—C24—C25	−0.1
C14—C9—C10—C11	−0.8 (5)	C23—C22—C27—C26	−0.3
C15—C16—C17—C18	−0.9 (6)	C23—C24—C25—C26	−0.1
C16—C15—C20—C19	0.3 (5)	C24—C25—C26—C27	0.1
C16—C15—N1—C1	−49.8 (4)	C25—C26—C27—C22	0.1
C16—C15—N1—C2	126.4 (3)	C27—C22—C23—C24	0.3
C16—C17—C18—C19	0.4 (6)

Hydrogen-bond geometry (Å, º)

Cg(X) = center of gravity of ring (X); D—H···Cg(X) = angle of the D—H bond with the π plane

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg5	0.98	2.66	3.5802 (6)	156
C6—H6···Cg3^i	0.93	2.83	3.6823 (6)	153

Symmetry code: (i) −x−1, −y, −z.