Ethyl 4-(4,5-dimeth­oxy-2-nitro­phen­yl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

In the title compound, C₂₂H₂₃N₃O₆S, the pyridimine ring adopts a screw boat conformation, with one C and one N atom displaced from the plane of the remaining atoms. In the crystal structure, centrosymmetric dimers are formed via pairs of N—H...S hydrogen bonds. The keto O atom of the ester group is disordered equally over two positions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.044
• wR factor = 0.130
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O5     ..  N1      ..       2.82 Ang.

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O5'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5'    ..  C6      ..       3.01 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.20 Deg.
              O5   -C13  -O5'     1.555   1.555   1.555

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          R

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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

---

S1. Comment

As part of our ongoing strudies of biologically active molecules (Kumaradhas et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

Within the 1,4–pyridimine ring, the C10—N2 and C10—N3 bonds are somewhat short, and the C1—C2 bond of the substituent 2–nitro–4,5–dimethoxy phenyl ring is lengthened, probably due to steric factors. The pyridimine ring shows a distorted envelope conformation in which C9 and N3 lie above the mean plane of the other ring atoms, having deviations of 0.303 (1)Å and 0.144 (1)Å respectively.

The dihedral angle of the pendant phenyl and aromatic rings with the central ring are 85.9 (1)° and 86.4 (1)° respectively, which marks the near-perpendicularity of both the rings.

In the crystal, the molecules of (I) form inversion dimers (Table 1, Fig. 2) via pairs of N—H···S hydrogen bonds thus generating R₂²(8) loops. A weak C—H···O interaction also occurs.

Related literature

For related literature, see: Kumaradhas et al. (2007).

S2. Experimental

A mixture of 2-nitroveratraldehyde (0.01 mol), ethylaceto acetate (0.015 mole), thiourea (0.01 mol) and concentrated sulfuric acid (1–2 drops) in ethanol (10 ml) taken in a borosil beaker (100 ml capacity) was zapped inside a microwave oven for 3–4 minutes (power = 160 watt). The reaction mixture was then allowed to stand at room temperature and poured into water. The product separated was filtered, washed with water followed by ethanol, dried and finally recrystallized from ethanol by slow evaporation at room temperature to yield pale yellow rectangular blocks of (I).

S3. Refinement

Atom O5 is disordered over two sites with equal occupancies. All the H atoms were placed geometrically (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(methyl C).

Computing details

Data collection: APEX (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of (I), showing 50% displacement ellipsoids and arbitrary spheres for the H atoms. Only one orientation of the disordered atom O5 is shown.
	Fig. 2. Part of the crystal structure of (I), showing the formation of an R2^2(8) dimer. Atoms marked with an asterisk (*) are at the symmetry positions (1 - x, 2 - y, 1 - z). The H atoms not involved in these motifs shown have been omitted.

Ethyl 4-(4,5-dimethoxy-2-nitrophenyl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-τetrahydropyrimidine-5-carboxylate

Crystal data

C22H23N3O6S	Z = 2
Mr = 457.49	F(000) = 480
Triclinic, P1	Dx = 1.334 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1475 (8) Å	Cell parameters from 25 reflections
b = 10.3588 (10) Å	θ = 5–11°
c = 14.8263 (15) Å	µ = 0.19 mm^−1
α = 86.620 (2)°	T = 296 K
β = 78.262 (2)°	Block, pale yellow
γ = 68.395 (2)°	0.21 × 0.11 × 0.08 mm
V = 1138.90 (19) Å^3

Data collection

Bruker APEX II CCD diffractometer	Rint = 0.017
ω scans	θmax = 28.0°, θmin = 2.1°
13201 measured reflections	h = −10→10
5229 independent reflections	k = −13→13
4549 reflections with I > 2σ(I)	l = −19→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0709P)^2 + 0.188P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.32 e Å^−3
5229 reflections	Δρmin = −0.22 e Å^−3
302 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S	0.45829 (6)	0.83000 (4)	0.43847 (3)	0.05704 (14)
O1	0.66977 (18)	0.55834 (12)	0.92626 (9)	0.0652 (3)
O2	0.52874 (18)	0.47350 (11)	0.81277 (8)	0.0621 (3)
O3	0.3863 (2)	1.11302 (13)	0.77587 (9)	0.0747 (4)
O4	0.38192 (18)	1.07621 (12)	0.92019 (8)	0.0638 (3)
O5	−0.2304 (13)	0.9803 (10)	0.8041 (8)	0.090 (2)	0.5
O5'	−0.1923 (13)	0.9289 (10)	0.8221 (8)	0.089 (2)	0.5
O6	−0.04308 (15)	1.06751 (13)	0.83484 (8)	0.0618 (3)
N1	0.39604 (17)	1.03669 (12)	0.84201 (9)	0.0473 (3)
N2	0.32962 (15)	0.93324 (12)	0.60670 (8)	0.0424 (3)
H2	0.3986	0.9801	0.5912	0.051*
N3	0.18386 (16)	0.80205 (12)	0.56207 (8)	0.0447 (3)
C1	0.56626 (19)	0.65847 (15)	0.87698 (10)	0.0461 (3)
C2	0.4914 (2)	0.61169 (14)	0.81356 (10)	0.0457 (3)
C3	0.38765 (19)	0.70637 (14)	0.75925 (9)	0.0434 (3)
H3	0.3384	0.6746	0.718	0.052*
C4	0.35371 (17)	0.84891 (13)	0.76403 (8)	0.0372 (3)
C5	0.42686 (17)	0.89020 (13)	0.82832 (9)	0.0381 (3)
C6	0.53023 (18)	0.79808 (14)	0.88500 (9)	0.0429 (3)
H6	0.5748	0.8307	0.9281	0.052*
C7	0.7410 (3)	0.6026 (2)	0.99266 (16)	0.0827 (6)
H7A	0.8186	0.6497	0.9626	0.124*
H7B	0.8086	0.5235	1.0242	0.124*
H7C	0.6444	0.6649	1.0362	0.124*
C8	0.4525 (3)	0.41968 (18)	0.75192 (14)	0.0709 (5)
H8A	0.3236	0.4612	0.7673	0.106*
H8B	0.4892	0.3208	0.7582	0.106*
H8C	0.4936	0.441	0.6895	0.106*
C9	0.23486 (17)	0.94602 (13)	0.70240 (9)	0.0384 (3)
H9	0.2029	1.0416	0.7236	0.046*
C10	0.31935 (18)	0.85618 (13)	0.54131 (9)	0.0411 (3)
C11	0.04369 (18)	0.84849 (14)	0.64043 (10)	0.0437 (3)
C12	0.06332 (18)	0.92001 (14)	0.70715 (10)	0.0421 (3)
C13	−0.0804 (2)	0.97947 (18)	0.78865 (11)	0.0547 (4)
C14	−0.1783 (3)	1.1408 (2)	0.91359 (14)	0.0761 (5)
H14A	−0.2157	1.0754	0.954	0.091*
H14B	−0.2831	1.2066	0.8929	0.091*
C15	−0.0993 (3)	1.2135 (3)	0.96261 (17)	0.0924 (7)
H15A	0.0002	1.1472	0.9857	0.139*
H15B	−0.1884	1.2664	1.0131	0.139*
H15C	−0.0577	1.2748	0.9213	0.139*
C16	−0.1218 (2)	0.8164 (2)	0.63980 (14)	0.0648 (4)
H16A	−0.2048	0.8462	0.6973	0.097*
H16B	−0.0885	0.7182	0.6316	0.097*
H16C	−0.1776	0.8643	0.5902	0.097*
C17	0.1732 (2)	0.71097 (15)	0.49452 (10)	0.0456 (3)
C18	0.2479 (2)	0.56988 (15)	0.50319 (11)	0.0495 (3)
H18	0.3075	0.5323	0.5513	0.059*
C19	0.2334 (2)	0.48365 (17)	0.43937 (13)	0.0602 (4)
H19	0.2839	0.3878	0.4446	0.072*
C20	0.1453 (3)	0.53926 (19)	0.36889 (13)	0.0667 (5)
H20	0.1357	0.4812	0.3264	0.08*
C21	0.0711 (3)	0.6803 (2)	0.36084 (14)	0.0750 (5)
H21	0.0114	0.7178	0.3127	0.09*
C22	0.0843 (3)	0.76721 (18)	0.42366 (13)	0.0653 (5)
H22	0.0336	0.863	0.4182	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0731 (3)	0.0625 (3)	0.0431 (2)	−0.0406 (2)	0.00476 (17)	−0.00769 (16)
O1	0.0813 (8)	0.0456 (6)	0.0700 (7)	−0.0122 (6)	−0.0376 (6)	−0.0021 (5)
O2	0.0946 (9)	0.0369 (5)	0.0626 (7)	−0.0250 (6)	−0.0302 (6)	−0.0007 (5)
O3	0.1192 (11)	0.0593 (7)	0.0756 (8)	−0.0612 (8)	−0.0346 (8)	0.0162 (6)
O4	0.0815 (8)	0.0499 (6)	0.0617 (7)	−0.0215 (6)	−0.0166 (6)	−0.0194 (5)
O5	0.050 (2)	0.132 (7)	0.093 (5)	−0.047 (4)	0.014 (2)	−0.040 (4)
O5'	0.080 (5)	0.122 (6)	0.079 (4)	−0.071 (5)	0.026 (3)	−0.019 (3)
O6	0.0557 (6)	0.0628 (7)	0.0611 (7)	−0.0246 (5)	0.0126 (5)	−0.0179 (5)
N1	0.0533 (7)	0.0435 (6)	0.0530 (7)	−0.0261 (5)	−0.0100 (5)	−0.0051 (5)
N2	0.0493 (6)	0.0475 (6)	0.0393 (6)	−0.0309 (5)	−0.0028 (5)	0.0008 (4)
N3	0.0509 (6)	0.0445 (6)	0.0470 (6)	−0.0272 (5)	−0.0085 (5)	−0.0019 (5)
C1	0.0484 (7)	0.0447 (7)	0.0446 (7)	−0.0150 (6)	−0.0096 (6)	−0.0055 (6)
C2	0.0574 (8)	0.0368 (7)	0.0449 (7)	−0.0193 (6)	−0.0089 (6)	−0.0048 (5)
C3	0.0526 (7)	0.0403 (7)	0.0425 (7)	−0.0216 (6)	−0.0102 (6)	−0.0056 (5)
C4	0.0393 (6)	0.0387 (6)	0.0356 (6)	−0.0195 (5)	−0.0004 (5)	−0.0044 (5)
C5	0.0388 (6)	0.0379 (6)	0.0398 (6)	−0.0199 (5)	0.0007 (5)	−0.0074 (5)
C6	0.0435 (7)	0.0470 (7)	0.0417 (7)	−0.0202 (6)	−0.0061 (5)	−0.0081 (5)
C7	0.1015 (15)	0.0638 (11)	0.0877 (14)	−0.0146 (10)	−0.0580 (13)	−0.0021 (10)
C8	0.1120 (15)	0.0466 (9)	0.0721 (11)	−0.0417 (10)	−0.0328 (11)	−0.0006 (8)
C9	0.0419 (6)	0.0363 (6)	0.0395 (6)	−0.0198 (5)	−0.0023 (5)	−0.0018 (5)
C10	0.0479 (7)	0.0380 (6)	0.0419 (7)	−0.0216 (6)	−0.0079 (5)	0.0035 (5)
C11	0.0423 (7)	0.0399 (7)	0.0529 (8)	−0.0205 (6)	−0.0086 (6)	0.0044 (5)
C12	0.0402 (7)	0.0411 (7)	0.0471 (7)	−0.0193 (5)	−0.0057 (5)	0.0038 (5)
C13	0.0459 (8)	0.0655 (9)	0.0538 (8)	−0.0257 (7)	−0.0007 (6)	−0.0023 (7)
C14	0.0600 (10)	0.0847 (13)	0.0672 (11)	−0.0180 (10)	0.0148 (9)	−0.0229 (10)
C15	0.0887 (15)	0.0849 (15)	0.0886 (15)	−0.0272 (12)	0.0184 (12)	−0.0394 (12)
C16	0.0544 (9)	0.0724 (11)	0.0808 (12)	−0.0386 (9)	−0.0101 (8)	−0.0065 (9)
C17	0.0536 (8)	0.0428 (7)	0.0486 (7)	−0.0256 (6)	−0.0124 (6)	0.0004 (6)
C18	0.0551 (8)	0.0448 (7)	0.0536 (8)	−0.0226 (6)	−0.0144 (6)	0.0044 (6)
C19	0.0711 (10)	0.0429 (8)	0.0718 (11)	−0.0268 (7)	−0.0126 (8)	−0.0043 (7)
C20	0.0886 (13)	0.0644 (10)	0.0639 (10)	−0.0435 (10)	−0.0193 (9)	−0.0084 (8)
C21	0.1055 (15)	0.0693 (11)	0.0692 (11)	−0.0398 (11)	−0.0457 (11)	0.0091 (9)
C22	0.0893 (13)	0.0454 (8)	0.0726 (11)	−0.0266 (8)	−0.0392 (10)	0.0089 (7)

Geometric parameters (Å, º)

S—C10	1.6733 (14)	C7—H7C	0.96
O1—C1	1.3558 (18)	C8—H8A	0.96
O1—C7	1.414 (2)	C8—H8B	0.96
O2—C2	1.3496 (16)	C8—H8C	0.96
O2—C8	1.433 (2)	C9—C12	1.5053 (17)
O3—N1	1.2195 (17)	C9—H9	0.98
O4—N1	1.2212 (16)	C11—C12	1.3383 (19)
O5—C13	1.194 (10)	C11—C16	1.505 (2)
O5'—C13	1.221 (10)	C12—C13	1.480 (2)
O6—C13	1.325 (2)	C14—C15	1.457 (3)
O6—C14	1.456 (2)	C14—H14A	0.97
N1—C5	1.4635 (16)	C14—H14B	0.97
N2—C10	1.3257 (17)	C15—H15A	0.96
N2—C9	1.4588 (16)	C15—H15B	0.96
N2—H2	0.86	C15—H15C	0.96
N3—C10	1.3874 (17)	C16—H16A	0.96
N3—C11	1.4166 (18)	C16—H16B	0.96
N3—C17	1.4518 (17)	C16—H16C	0.96
C1—C6	1.3730 (19)	C17—C18	1.370 (2)
C1—C2	1.4128 (19)	C17—C22	1.376 (2)
C2—C3	1.378 (2)	C18—C19	1.389 (2)
C3—C4	1.4020 (18)	C18—H18	0.93
C3—H3	0.93	C19—C20	1.367 (3)
C4—C5	1.3833 (17)	C19—H19	0.93
C4—C9	1.5228 (18)	C20—C21	1.369 (3)
C5—C6	1.388 (2)	C20—H20	0.93
C6—H6	0.93	C21—C22	1.379 (2)
C7—H7A	0.96	C21—H21	0.93
C7—H7B	0.96	C22—H22	0.93
C1—O1—C7	116.94 (13)	N3—C10—S	122.04 (10)
C2—O2—C8	117.96 (12)	C12—C11—N3	119.26 (12)
C13—O6—C14	117.29 (14)	C12—C11—C16	124.83 (14)
O3—N1—O4	123.17 (13)	N3—C11—C16	115.88 (13)
O3—N1—C5	119.24 (12)	C11—C12—C13	122.83 (13)
O4—N1—C5	117.60 (12)	C11—C12—C9	121.15 (12)
C10—N2—C9	126.12 (11)	C13—C12—C9	116.02 (12)
C10—N2—H2	116.9	O5—C13—O5'	28.2 (6)
C9—N2—H2	116.9	O5—C13—O6	118.7 (6)
C10—N3—C11	121.49 (11)	O5'—C13—O6	122.6 (6)
C10—N3—C17	118.25 (12)	O5—C13—C12	127.9 (6)
C11—N3—C17	119.66 (11)	O5'—C13—C12	123.7 (6)
O1—C1—C6	124.99 (13)	O6—C13—C12	111.26 (12)
O1—C1—C2	115.74 (12)	O6—C14—C15	108.14 (16)
C6—C1—C2	119.27 (13)	O6—C14—H14A	110.1
O2—C2—C3	125.40 (12)	C15—C14—H14A	110.1
O2—C2—C1	115.11 (13)	O6—C14—H14B	110.1
C3—C2—C1	119.49 (12)	C15—C14—H14B	110.1
C2—C3—C4	122.31 (12)	H14A—C14—H14B	108.4
C2—C3—H3	118.8	C14—C15—H15A	109.5
C4—C3—H3	118.8	C14—C15—H15B	109.5
C5—C4—C3	116.15 (12)	H15A—C15—H15B	109.5
C5—C4—C9	125.22 (11)	C14—C15—H15C	109.5
C3—C4—C9	118.58 (11)	H15A—C15—H15C	109.5
C4—C5—C6	123.17 (12)	H15B—C15—H15C	109.5
C4—C5—N1	121.33 (12)	C11—C16—H16A	109.5
C6—C5—N1	115.50 (11)	C11—C16—H16B	109.5
C1—C6—C5	119.56 (12)	H16A—C16—H16B	109.5
C1—C6—H6	120.2	C11—C16—H16C	109.5
C5—C6—H6	120.2	H16A—C16—H16C	109.5
O1—C7—H7A	109.5	H16B—C16—H16C	109.5
O1—C7—H7B	109.5	C18—C17—C22	120.62 (14)
H7A—C7—H7B	109.5	C18—C17—N3	119.71 (13)
O1—C7—H7C	109.5	C22—C17—N3	119.65 (13)
H7A—C7—H7C	109.5	C17—C18—C19	119.26 (14)
H7B—C7—H7C	109.5	C17—C18—H18	120.4
O2—C8—H8A	109.5	C19—C18—H18	120.4
O2—C8—H8B	109.5	C20—C19—C18	120.23 (15)
H8A—C8—H8B	109.5	C20—C19—H19	119.9
O2—C8—H8C	109.5	C18—C19—H19	119.9
H8A—C8—H8C	109.5	C19—C20—C21	120.08 (16)
H8B—C8—H8C	109.5	C19—C20—H20	120
N2—C9—C12	109.01 (10)	C21—C20—H20	120
N2—C9—C4	111.33 (11)	C20—C21—C22	120.35 (16)
C12—C9—C4	112.06 (10)	C20—C21—H21	119.8
N2—C9—H9	108.1	C22—C21—H21	119.8
C12—C9—H9	108.1	C17—C22—C21	119.46 (16)
C4—C9—H9	108.1	C17—C22—H22	120.3
N2—C10—N3	116.24 (12)	C21—C22—H22	120.3
N2—C10—S	121.69 (10)
C7—O1—C1—C6	1.9 (2)	C17—N3—C10—S	5.02 (18)
C7—O1—C1—C2	−177.74 (17)	C10—N3—C11—C12	−16.1 (2)
C8—O2—C2—C3	−1.2 (2)	C17—N3—C11—C12	172.90 (12)
C8—O2—C2—C1	178.20 (15)	C10—N3—C11—C16	161.79 (14)
O1—C1—C2—O2	2.0 (2)	C17—N3—C11—C16	−9.19 (19)
C6—C1—C2—O2	−177.72 (13)	N3—C11—C12—C13	176.31 (13)
O1—C1—C2—C3	−178.59 (14)	C16—C11—C12—C13	−1.4 (2)
C6—C1—C2—C3	1.7 (2)	N3—C11—C12—C9	−2.9 (2)
O2—C2—C3—C4	179.72 (14)	C16—C11—C12—C9	179.39 (14)
C1—C2—C3—C4	0.3 (2)	N2—C9—C12—C11	21.97 (17)
C2—C3—C4—C5	−1.5 (2)	C4—C9—C12—C11	−101.72 (14)
C2—C3—C4—C9	−178.99 (13)	N2—C9—C12—C13	−157.29 (12)
C3—C4—C5—C6	0.75 (19)	C4—C9—C12—C13	79.02 (15)
C9—C4—C5—C6	178.01 (12)	C14—O6—C13—O5	11.5 (5)
C3—C4—C5—N1	−177.98 (12)	C14—O6—C13—O5'	−21.1 (5)
C9—C4—C5—N1	−0.71 (19)	C14—O6—C13—C12	176.21 (15)
O3—N1—C5—C4	−35.34 (19)	C11—C12—C13—O5	−4.6 (5)
O4—N1—C5—C4	144.93 (13)	C9—C12—C13—O5	174.6 (5)
O3—N1—C5—C6	145.85 (14)	C11—C12—C13—O5'	29.9 (6)
O4—N1—C5—C6	−33.89 (17)	C9—C12—C13—O5'	−150.8 (5)
O1—C1—C6—C5	177.86 (14)	C11—C12—C13—O6	−167.62 (14)
C2—C1—C6—C5	−2.5 (2)	C9—C12—C13—O6	11.62 (19)
C4—C5—C6—C1	1.3 (2)	C13—O6—C14—C15	170.88 (19)
N1—C5—C6—C1	−179.94 (12)	C10—N3—C17—C18	97.45 (16)
C10—N2—C9—C12	−27.44 (18)	C11—N3—C17—C18	−91.28 (17)
C10—N2—C9—C4	96.69 (15)	C10—N3—C17—C22	−84.14 (19)
C5—C4—C9—N2	108.95 (13)	C11—N3—C17—C22	87.13 (18)
C3—C4—C9—N2	−73.85 (14)	C22—C17—C18—C19	0.2 (2)
C5—C4—C9—C12	−128.66 (13)	N3—C17—C18—C19	178.56 (14)
C3—C4—C9—C12	48.54 (16)	C17—C18—C19—C20	−0.1 (3)
C9—N2—C10—N3	11.6 (2)	C18—C19—C20—C21	0.1 (3)
C9—N2—C10—S	−170.21 (11)	C19—C20—C21—C22	−0.1 (3)
C11—N3—C10—N2	12.12 (19)	C18—C17—C22—C21	−0.2 (3)
C17—N3—C10—N2	−176.78 (12)	N3—C17—C22—C21	−178.56 (17)
C11—N3—C10—S	−166.08 (10)	C20—C21—C22—C17	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S^i	0.86	2.61	3.4505 (11)	167
C8—H8B···O3^ii	0.96	2.56	3.400 (2)	146

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