1-[1-(3-Methyl-phen-yl)-5-phenyl-4-phenyl-sulfonyl-1H-pyrazol-3-yl]ethanone.

Both the acetyl and phenyl substituents of the central pyrazole ring in the title compound, C(24)H(20)N(2)O(3)S, are twisted with respect to the pyrazole ring, with the twist involving the phenyl ring being greater [67.4 (1) and 29.6 (2)°]. The tolyl substituent is disordered over two positions in a 1:1 ratio; the mean planes of the aromatic ring are aligned at 67.7 (3) and 69.4 (3)° with respect to the pyrazole ring.

Related literature

For the synthesis of this class of pyrazoles, which have been tested as anti-inflammatory agents, see: Nasser et al. (2011 ▶).

Experimental

Crystal data

C24H20N2O3S

M = 416.48

Monoclinic,

a = 10.5717 (4) Å

b = 17.7004 (6) Å

c = 12.8744 (4) Å

β = 115.945 (1)°

V = 2166.30 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.933, T max = 0.966

23603 measured reflections

4951 independent reflections

3490 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.131

S = 1.16

4951 reflections

266 parameters

44 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041122/hg5108sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041122/hg5108Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041122/hg5108Isup3.cml

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

C24H20N2O3S	F(000) = 872
Mr = 416.48	Dx = 1.277 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 725 reflections
a = 10.5717 (4) Å	θ = 3.1–27.5°
b = 17.7004 (6) Å	µ = 0.18 mm−1
c = 12.8744 (4) Å	T = 293 K
β = 115.945 (1)°	Block, yellow
V = 2166.30 (13) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4951 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −13→13
Tmin = 0.933, Tmax = 0.966	k = −22→22
23603 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.3317P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
4951 reflections	Δρmax = 0.30 e Å−3
266 parameters	Δρmin = −0.37 e Å−3
44 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0235 (19)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.54751 (5)	0.63143 (2)	0.45045 (4)	0.03997 (16)
O1	0.40174 (15)	0.64090 (7)	0.42277 (13)	0.0545 (4)
O2	0.64729 (16)	0.62701 (7)	0.56934 (11)	0.0534 (4)
O3	0.88191 (16)	0.55753 (8)	0.54515 (13)	0.0637 (4)
N1	0.50448 (17)	0.45192 (8)	0.26398 (13)	0.0440 (4)
N2	0.63866 (17)	0.43781 (9)	0.34261 (13)	0.0460 (4)
C1	0.8879 (2)	0.42371 (13)	0.5538 (2)	0.0624 (6)
H1A	0.9853	0.4310	0.6057	0.094*
H1B	0.8804	0.3920	0.4909	0.094*
H1C	0.8409	0.4001	0.5944	0.094*
C2	0.8211 (2)	0.49846 (11)	0.50784 (17)	0.0452 (4)
C3	0.67586 (19)	0.49709 (9)	0.41353 (15)	0.0405 (4)
C4	0.56201 (19)	0.54928 (9)	0.38003 (14)	0.0382 (4)
C5	0.45247 (19)	0.51785 (9)	0.28374 (15)	0.0388 (4)
C6	0.3067 (2)	0.54191 (10)	0.21258 (15)	0.0431 (4)
C7	0.1966 (2)	0.50136 (12)	0.21653 (18)	0.0551 (5)
H7	0.2151	0.4584	0.2624	0.066*
C8	0.0593 (2)	0.52496 (16)	0.1521 (2)	0.0722 (7)
H8	−0.0146	0.4975	0.1542	0.087*
C9	0.0319 (3)	0.58849 (17)	0.0853 (2)	0.0803 (7)
H9	−0.0604	0.6048	0.0437	0.096*
C10	0.1397 (3)	0.62815 (15)	0.0796 (2)	0.0822 (8)
H10	0.1204	0.6708	0.0331	0.099*
C11	0.2772 (3)	0.60493 (13)	0.14280 (19)	0.0631 (6)
H11	0.3501	0.6319	0.1383	0.076*
C12	0.4517 (7)	0.3942 (4)	0.1774 (6)	0.0362 (12)	0.50
C13	0.4027 (10)	0.3246 (6)	0.1945 (5)	0.0663 (7)	0.50
H13	0.4246	0.3081	0.2690	0.080*	0.50
C14	0.3208 (9)	0.2798 (4)	0.1002 (8)	0.0720 (15)	0.50
H14	0.2880	0.2333	0.1116	0.086*	0.50
C15	0.2879 (7)	0.3045 (4)	−0.0112 (6)	0.0686 (16)	0.50
H15	0.2331	0.2745	−0.0742	0.082*	0.50
C16	0.3369 (10)	0.3741 (6)	−0.0283 (5)	0.0685 (10)	0.50
C17	0.4188 (8)	0.4189 (4)	0.0660 (8)	0.0459 (12)	0.50
H17	0.4516	0.4654	0.0545	0.055*	0.50
C18	0.2992 (15)	0.3922 (5)	−0.1542 (5)	0.1145 (12)	0.50
H18A	0.2297	0.4315	−0.1807	0.172*	0.50
H18B	0.2623	0.3478	−0.2005	0.172*	0.50
H18C	0.3819	0.4087	−0.1608	0.172*	0.50
C12'	0.4183 (7)	0.4036 (4)	0.1680 (6)	0.0362 (12)	0.50
C13'	0.4065 (10)	0.3301 (6)	0.2006 (4)	0.0663 (7)	0.50
H13'	0.4309	0.3190	0.2776	0.080*	0.50
C14'	0.3584 (9)	0.2731 (4)	0.1180 (8)	0.0720 (15)	0.50
H14'	0.3505	0.2239	0.1398	0.086*	0.50
C15'	0.3219 (8)	0.2897 (4)	0.0029 (6)	0.0686 (16)	0.50
H15'	0.2897	0.2516	−0.0524	0.082*	0.50
C16'	0.3337 (10)	0.3633 (6)	−0.0297 (4)	0.0685 (10)	0.50
C17'	0.3819 (8)	0.4203 (4)	0.0529 (8)	0.0459 (12)	0.50
H17'	0.3898	0.4695	0.0312	0.055*	0.50
C18'	0.2985 (14)	0.3918 (2)	−0.1529 (2)	0.1145 (12)	0.50
H18D	0.2052	0.3758	−0.2049	0.172*	0.50
H18E	0.3648	0.3712	−0.1776	0.172*	0.50
H18F	0.3034	0.4459	−0.1527	0.172*	0.50
C19	0.59640 (16)	0.70713 (9)	0.38558 (12)	0.0420 (4)
C20	0.73709 (16)	0.72002 (10)	0.41591 (12)	0.0567 (5)
H20	0.8059	0.6889	0.4690	0.068*
C21	0.7737 (3)	0.78024 (14)	0.3657 (2)	0.0777 (7)
H21	0.8679	0.7898	0.3853	0.093*
C22	0.6707 (4)	0.82612 (15)	0.2866 (2)	0.0850 (9)
H22	0.6961	0.8661	0.2527	0.102*
C23	0.5320 (3)	0.81318 (13)	0.2580 (2)	0.0755 (7)
H23	0.4634	0.8446	0.2054	0.091*
C24	0.4932 (2)	0.75312 (11)	0.30731 (17)	0.0562 (5)
H24	0.3989	0.7440	0.2878	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0528 (3)	0.0324 (2)	0.0414 (3)	0.00075 (18)	0.0268 (2)	−0.00099 (17)
O1	0.0550 (9)	0.0472 (8)	0.0739 (10)	0.0037 (6)	0.0399 (8)	−0.0035 (7)
O2	0.0773 (10)	0.0465 (8)	0.0364 (7)	0.0045 (7)	0.0249 (7)	−0.0011 (5)
O3	0.0572 (10)	0.0547 (9)	0.0710 (10)	−0.0084 (7)	0.0205 (8)	−0.0132 (7)
N1	0.0500 (10)	0.0366 (8)	0.0474 (8)	−0.0036 (6)	0.0232 (8)	−0.0090 (6)
N2	0.0470 (9)	0.0415 (9)	0.0519 (9)	−0.0001 (7)	0.0239 (8)	−0.0062 (7)
C1	0.0521 (13)	0.0565 (13)	0.0761 (15)	0.0077 (10)	0.0259 (12)	0.0102 (11)
C2	0.0464 (11)	0.0466 (11)	0.0486 (10)	−0.0017 (8)	0.0264 (9)	−0.0043 (8)
C3	0.0470 (11)	0.0337 (9)	0.0464 (10)	−0.0019 (7)	0.0256 (9)	−0.0020 (7)
C4	0.0474 (10)	0.0319 (9)	0.0406 (9)	−0.0021 (7)	0.0242 (8)	−0.0010 (7)
C5	0.0473 (11)	0.0333 (9)	0.0408 (9)	−0.0027 (7)	0.0238 (8)	−0.0008 (7)
C6	0.0495 (11)	0.0381 (10)	0.0404 (9)	−0.0004 (8)	0.0184 (9)	−0.0012 (7)
C7	0.0516 (13)	0.0572 (13)	0.0562 (12)	0.0001 (9)	0.0234 (11)	0.0081 (9)
C8	0.0483 (14)	0.0915 (18)	0.0703 (15)	0.0003 (12)	0.0199 (12)	0.0094 (13)
C9	0.0616 (17)	0.091 (2)	0.0703 (16)	0.0187 (14)	0.0123 (13)	0.0107 (14)
C10	0.084 (2)	0.0708 (17)	0.0720 (16)	0.0151 (14)	0.0159 (15)	0.0280 (13)
C11	0.0649 (15)	0.0553 (13)	0.0619 (13)	−0.0018 (11)	0.0211 (12)	0.0165 (10)
C12	0.022 (3)	0.0355 (19)	0.0547 (14)	0.007 (2)	0.0206 (17)	−0.0108 (14)
C13	0.0873 (18)	0.0454 (16)	0.0844 (16)	−0.0160 (12)	0.0545 (15)	−0.0206 (12)
C14	0.063 (4)	0.0491 (16)	0.117 (3)	−0.016 (2)	0.051 (3)	−0.0338 (17)
C15	0.037 (4)	0.072 (3)	0.092 (2)	0.001 (3)	0.023 (2)	−0.046 (2)
C16	0.0551 (15)	0.085 (3)	0.0636 (14)	−0.0097 (16)	0.0246 (12)	−0.0338 (14)
C17	0.022 (4)	0.0633 (13)	0.049 (2)	−0.0071 (17)	0.012 (2)	−0.0137 (11)
C18	0.109 (3)	0.164 (3)	0.0582 (16)	−0.006 (2)	0.0247 (17)	−0.0346 (18)
C12'	0.022 (3)	0.0355 (19)	0.0547 (14)	0.007 (2)	0.0206 (17)	−0.0108 (14)
C13'	0.0873 (18)	0.0454 (16)	0.0844 (16)	−0.0160 (12)	0.0545 (15)	−0.0206 (12)
C14'	0.063 (4)	0.0491 (16)	0.117 (3)	−0.016 (2)	0.051 (3)	−0.0338 (17)
C15'	0.037 (4)	0.072 (3)	0.092 (2)	0.001 (3)	0.023 (2)	−0.046 (2)
C16'	0.0551 (15)	0.085 (3)	0.0636 (14)	−0.0097 (16)	0.0246 (12)	−0.0338 (14)
C17'	0.022 (4)	0.0633 (13)	0.049 (2)	−0.0071 (17)	0.012 (2)	−0.0137 (11)
C18'	0.109 (3)	0.164 (3)	0.0582 (16)	−0.006 (2)	0.0247 (17)	−0.0346 (18)
C19	0.0583 (12)	0.0319 (9)	0.0389 (9)	−0.0036 (8)	0.0241 (9)	−0.0048 (7)
C20	0.0614 (14)	0.0467 (11)	0.0677 (13)	−0.0072 (9)	0.0333 (11)	−0.0009 (10)
C21	0.0881 (19)	0.0641 (16)	0.0975 (19)	−0.0226 (14)	0.0560 (17)	−0.0040 (14)
C22	0.134 (3)	0.0551 (15)	0.0825 (18)	−0.0239 (16)	0.0628 (19)	0.0065 (13)
C23	0.112 (2)	0.0456 (13)	0.0597 (14)	−0.0017 (13)	0.0294 (15)	0.0126 (10)
C24	0.0689 (14)	0.0422 (11)	0.0514 (11)	0.0000 (9)	0.0208 (11)	0.0041 (9)

S1—O1	1.4316 (14)	C14—H14	0.9300
S1—O2	1.4314 (14)	C15—C16	1.3900
S1—C4	1.7554 (17)	C15—H15	0.9300
S1—C19	1.7713 (15)	C16—C17	1.3900
O3—C2	1.211 (2)	C16—C18	1.525 (6)
N1—N2	1.358 (2)	C17—H17	0.9300
N1—C5	1.361 (2)	C18—H18A	0.9600
N1—C12	1.434 (5)	C18—H18B	0.9600
N1—C12'	1.450 (5)	C18—H18C	0.9600
N2—C3	1.332 (2)	C12'—C13'	1.3900
C1—C2	1.495 (3)	C12'—C17'	1.3900
C1—H1A	0.9600	C13'—C14'	1.3900
C1—H1B	0.9600	C13'—H13'	0.9300
C1—H1C	0.9600	C14'—C15'	1.3900
C2—C3	1.484 (3)	C14'—H14'	0.9300
C3—C4	1.426 (2)	C15'—C16'	1.3900
C4—C5	1.390 (2)	C15'—H15'	0.9300
C5—C6	1.469 (3)	C16'—C17'	1.3900
C6—C11	1.380 (3)	C16'—C18'	1.547 (5)
C6—C7	1.387 (3)	C17'—H17'	0.9300
C7—C8	1.385 (3)	C18'—H18D	0.9600
C7—H7	0.9300	C18'—H18E	0.9600
C8—C9	1.367 (4)	C18'—H18F	0.9600
C8—H8	0.9300	C19—C24	1.381 (2)
C9—C10	1.368 (4)	C19—C20	1.382 (3)
C9—H9	0.9300	C20—C21	1.387 (3)
C10—C11	1.381 (3)	C20—H20	0.9300
C10—H10	0.9300	C21—C22	1.382 (4)
C11—H11	0.9300	C21—H21	0.9300
C12—C13	1.3900	C22—C23	1.366 (4)
C12—C17	1.3900	C22—H22	0.9300
C13—C14	1.3900	C23—C24	1.389 (3)
C13—H13	0.9300	C23—H23	0.9300
C14—C15	1.3900	C24—H24	0.9300
O1—S1—O2	118.81 (9)	C13—C14—C15	120.0
O1—S1—C4	107.23 (8)	C13—C14—H14	120.0
O2—S1—C4	108.48 (8)	C15—C14—H14	120.0
O1—S1—C19	107.36 (8)	C16—C15—C14	120.0
O2—S1—C19	108.37 (8)	C16—C15—H15	120.0
C4—S1—C19	105.89 (7)	C14—C15—H15	120.0
N2—N1—C5	113.22 (14)	C15—C16—C17	120.0
N2—N1—C12	111.9 (3)	C15—C16—C18	114.4 (7)
C5—N1—C12	134.9 (3)	C17—C16—C18	125.6 (7)
N2—N1—C12'	126.1 (3)	C16—C17—C12	120.0
C5—N1—C12'	120.7 (3)	C16—C17—H17	120.0
C3—N2—N1	105.36 (14)	C12—C17—H17	120.0
C2—C1—H1A	109.5	C13'—C12'—C17'	120.0
C2—C1—H1B	109.5	C13'—C12'—N1	113.7 (7)
H1A—C1—H1B	109.5	C17'—C12'—N1	124.2 (7)
C2—C1—H1C	109.5	C12'—C13'—C14'	120.0
H1A—C1—H1C	109.5	C12'—C13'—H13'	120.0
H1B—C1—H1C	109.5	C14'—C13'—H13'	120.0
O3—C2—C3	121.22 (18)	C13'—C14'—C15'	120.0
O3—C2—C1	122.0 (2)	C13'—C14'—H14'	120.0
C3—C2—C1	116.76 (17)	C15'—C14'—H14'	120.0
N2—C3—C4	110.24 (16)	C14'—C15'—C16'	120.0
N2—C3—C2	117.59 (16)	C14'—C15'—H15'	120.0
C4—C3—C2	132.17 (16)	C16'—C15'—H15'	120.0
C5—C4—C3	105.91 (15)	C17'—C16'—C15'	120.0
C5—C4—S1	124.43 (14)	C17'—C16'—C18'	113.1 (7)
C3—C4—S1	129.29 (14)	C15'—C16'—C18'	126.9 (7)
N1—C5—C4	105.25 (16)	C16'—C17'—C12'	120.0
N1—C5—C6	122.09 (16)	C16'—C17'—H17'	120.0
C4—C5—C6	132.64 (16)	C12'—C17'—H17'	120.0
C11—C6—C7	119.18 (19)	C16'—C18'—H18D	109.5
C11—C6—C5	121.16 (18)	C16'—C18'—H18E	109.5
C7—C6—C5	119.66 (16)	H18D—C18'—H18E	109.5
C8—C7—C6	119.9 (2)	C16'—C18'—H18F	109.5
C8—C7—H7	120.0	H18D—C18'—H18F	109.5
C6—C7—H7	120.0	H18E—C18'—H18F	109.5
C9—C8—C7	120.2 (2)	C24—C19—C20	121.21 (13)
C9—C8—H8	119.9	C24—C19—S1	119.32 (14)
C7—C8—H8	119.9	C20—C19—S1	119.46 (6)
C8—C9—C10	120.2 (2)	C19—C20—C21	118.73 (15)
C8—C9—H9	119.9	C19—C20—H20	120.6
C10—C9—H9	119.9	C21—C20—H20	120.6
C9—C10—C11	120.2 (2)	C22—C21—C20	120.3 (2)
C9—C10—H10	119.9	C22—C21—H21	119.8
C11—C10—H10	119.9	C20—C21—H21	119.8
C6—C11—C10	120.3 (2)	C23—C22—C21	120.4 (2)
C6—C11—H11	119.9	C23—C22—H22	119.8
C10—C11—H11	119.9	C21—C22—H22	119.8
C13—C12—C17	120.0	C22—C23—C24	120.1 (2)
C13—C12—N1	123.6 (7)	C22—C23—H23	119.9
C17—C12—N1	114.5 (7)	C24—C23—H23	119.9
C14—C13—C12	120.0	C19—C24—C23	119.2 (2)
C14—C13—H13	120.0	C19—C24—H24	120.4
C12—C13—H13	120.0	C23—C24—H24	120.4
C5—N1—N2—C3	−1.55 (19)	N2—N1—C12—C17	−116.8 (4)
C12—N1—N2—C3	177.1 (5)	C5—N1—C12—C17	61.4 (7)
C12'—N1—N2—C3	179.6 (5)	C12'—N1—C12—C17	71 (3)
N1—N2—C3—C4	0.88 (19)	C17—C12—C13—C14	0.0
N1—N2—C3—C2	−178.29 (14)	N1—C12—C13—C14	163.3 (5)
O3—C2—C3—N2	150.22 (18)	C12—C13—C14—C15	0.0
C1—C2—C3—N2	−29.7 (2)	C13—C14—C15—C16	0.0
O3—C2—C3—C4	−28.7 (3)	C14—C15—C16—C17	0.0
C1—C2—C3—C4	151.39 (19)	C14—C15—C16—C18	177.0 (10)
N2—C3—C4—C5	0.03 (19)	C15—C16—C17—C12	0.0
C2—C3—C4—C5	179.04 (18)	C18—C16—C17—C12	−176.7 (11)
N2—C3—C4—S1	173.15 (13)	C13—C12—C17—C16	0.0
C2—C3—C4—S1	−7.8 (3)	N1—C12—C17—C16	−164.8 (5)
O1—S1—C4—C5	22.34 (17)	N2—N1—C12'—C13'	54.4 (6)
O2—S1—C4—C5	151.81 (14)	C5—N1—C12'—C13'	−124.5 (3)
C19—S1—C4—C5	−92.06 (15)	C12—N1—C12'—C13'	64 (3)
O1—S1—C4—C3	−149.63 (16)	N2—N1—C12'—C17'	−108.7 (6)
O2—S1—C4—C3	−20.16 (18)	C5—N1—C12'—C17'	72.4 (6)
C19—S1—C4—C3	95.97 (16)	C12—N1—C12'—C17'	−99 (3)
N2—N1—C5—C4	1.57 (19)	C17'—C12'—C13'—C14'	0.0
C12—N1—C5—C4	−176.6 (6)	N1—C12'—C13'—C14'	−163.9 (6)
C12'—N1—C5—C4	−179.5 (5)	C12'—C13'—C14'—C15'	0.0
N2—N1—C5—C6	−176.67 (15)	C13'—C14'—C15'—C16'	0.0
C12—N1—C5—C6	5.1 (7)	C14'—C15'—C16'—C17'	0.0
C12'—N1—C5—C6	2.3 (5)	C14'—C15'—C16'—C18'	179.9 (11)
C3—C4—C5—N1	−0.93 (18)	C15'—C16'—C17'—C12'	0.0
S1—C4—C5—N1	−174.47 (12)	C18'—C16'—C17'—C12'	−179.9 (9)
C3—C4—C5—C6	177.05 (17)	C13'—C12'—C17'—C16'	0.0
S1—C4—C5—C6	3.5 (3)	N1—C12'—C17'—C16'	162.1 (6)
N1—C5—C6—C11	−113.8 (2)	O1—S1—C19—C24	−10.71 (16)
C4—C5—C6—C11	68.5 (3)	O2—S1—C19—C24	−140.20 (14)
N1—C5—C6—C7	67.2 (2)	C4—S1—C19—C24	103.59 (15)
C4—C5—C6—C7	−110.5 (2)	O1—S1—C19—C20	167.98 (11)
C11—C6—C7—C8	−0.9 (3)	O2—S1—C19—C20	38.50 (12)
C5—C6—C7—C8	178.2 (2)	C4—S1—C19—C20	−77.71 (12)
C6—C7—C8—C9	−0.6 (4)	C24—C19—C20—C21	−0.3 (2)
C7—C8—C9—C10	1.6 (4)	S1—C19—C20—C21	−178.99 (16)
C8—C9—C10—C11	−1.1 (4)	C19—C20—C21—C22	−0.2 (3)
C7—C6—C11—C10	1.4 (3)	C20—C21—C22—C23	0.7 (4)
C5—C6—C11—C10	−177.7 (2)	C21—C22—C23—C24	−0.7 (4)
C9—C10—C11—C6	−0.4 (4)	C20—C19—C24—C23	0.3 (3)
N2—N1—C12—C13	79.0 (4)	S1—C19—C24—C23	178.96 (16)
C5—N1—C12—C13	−102.8 (6)	C22—C23—C24—C19	0.2 (3)
C12'—N1—C12—C13	−93 (3)