Synthesis, crystal structure and cytotoxic activity of novel 5-methyl-4-thio­pyrimidine derivatives

This article presents the synthesis of three new 4-thio­pyrimidine derivatives obtained from ethyl 4-methyl-2-phenyl-6-sulfanyl­pyrimidine-5-carboxyl­ate as the starting material, namely, ethyl 4-[(4-chloro­benz­yl)sulfan­yl]-6-methyl-2-phenyl­pyrimidine-5-carboxyl­ate, C₂₁H₁₉ClN₂O₂S, (2), {4-[(4-chloro­benz­yl)sulfan­yl]-6-methyl-2-phenyl­pyrimidin-5-yl}methanol, C₁₉H₁₇ClN₂OS, (3), and 4-[(4-chloro­benz­yl)sulfan­yl]-5,6-dimethyl-2-phenyl­pyrimidine, C₁₉H₁₇ClN₂S, (4), which vary in the substituent at the 5-position of the pyrimidine ring. The compounds were characterized by ¹H NMR, ¹³C NMR, IR and mass spectroscopies, and also elemental analysis. The mol­ecular structures were further studied by single-crystal X-ray diffraction. Compound (2) crystallizes in the space group P with one mol­ecule in the asymmetric unit, whereas compounds (3) and (4) crystallize in the space group P2₁/c with two and one mol­ecule, respectively, in their asymmetric units. The conformation of each mol­ecule is best defined by the dihedral angles formed between the pyrimidine ring and the planes of the two aryl substituents attached at the 2- and 4-positions. The only structural difference between the three compounds is the substituent at the 5-position of the pyrimidine ring, but they present significantly different features in the hydrogen-bond inter­actions. Compound (2) displays a one-dimensional chain formed by hydrogen bonds and the chains are further extended into a two-dimensional network. Mol­ecules of (3) and (4) generate one-dimensional chains formed through inter­molecular inter­actions. The study examines the cytotoxicity of compounds (3) and (4) against Human umbilical vein endothelial cells (HUVEC) and HeLa, K562 and CFPAC cancer cell lines. The presence of the hy­droxy­methyl and methyl groups in (3) and (4), respectively, offers an inter­esting new insight into the structures and behaviour of these derivatives. Compound (4) was found to be nontoxic against CFPAC and HUVEC; however, it shows weak activity against the HeLa and K563 cell lines. The presence of a hy­droxy group in (3) significantly increases its cytotoxicity towards both, i.e. the cancer (HeLa, K562 and CFPAC) and normal (HUVEC) cell lines.

Computing details

For all structures, data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2014); software used to prepare material for publication: PLATON (Spek, 2009).

Ethyl 4-[(4-chlorobenzyl)sulfanyl]-6-methyl-2-phenylpyrimidine-5-carboxylate (2)

Crystal data

C21H19ClN2O2S	F(000) = 416
Mr = 398.89	Dx = 1.402 Mg m^−3
Triclinic, P1	Melting point: 360 K
a = 7.8332 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.401 (2) Å	Cell parameters from 6878 reflections
c = 12.166 (3) Å	θ = 3.1–28.0°
α = 76.05 (2)°	µ = 0.33 mm^−1
β = 84.86 (2)°	T = 100 K
γ = 79.63 (2)°	Needle, colourless
V = 945.1 (4) Å^3	0.42 × 0.30 × 0.12 mm
Z = 2

Data collection

Agilent Xcalibur Sapphire2, large Be window diffractometer	4461 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4002 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 8.3359 pixels mm^-1	θmax = 28.1°, θmin = 3.1°
ω scans	h = −10→7
Absorption correction: analytical CrysAlis PRO (Agilent, 2012), Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)	k = −13→13
Tmin = 0.896, Tmax = 0.963	l = −15→16
8817 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0886P)^2 + 0.4144P] where P = (Fo^2 + 2Fc^2)/3
4461 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.51 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
Cl1	0.72878 (6)	0.77464 (5)	0.96609 (4)	0.02398 (15)
S1	0.02488 (5)	0.67866 (4)	0.71019 (3)	0.01522 (14)
N1	0.29616 (17)	0.45852 (14)	0.45025 (12)	0.0146 (3)
C2	0.3081 (2)	0.41419 (16)	0.56249 (13)	0.0138 (3)
N3	0.22807 (18)	0.47817 (14)	0.64066 (11)	0.0142 (3)
C4	0.1271 (2)	0.59609 (16)	0.60479 (13)	0.0133 (3)
C5	0.1020 (2)	0.65182 (16)	0.48774 (13)	0.0136 (3)
C6	0.1933 (2)	0.57659 (16)	0.41265 (13)	0.0140 (3)
C21	0.4188 (2)	0.28249 (17)	0.60521 (14)	0.0156 (3)
C22	0.5103 (2)	0.21037 (17)	0.52934 (15)	0.0189 (4)
H22	0.499997	0.244781	0.450044	0.023*
C23	0.6166 (2)	0.08838 (18)	0.56941 (16)	0.0227 (4)
H23	0.679631	0.040162	0.517456	0.027*
C24	0.6306 (2)	0.03704 (18)	0.68522 (16)	0.0226 (4)
H24	0.704589	−0.045648	0.712403	0.027*
C25	0.5366 (3)	0.10640 (19)	0.76158 (16)	0.0241 (4)
H25	0.543732	0.070032	0.840852	0.029*
C26	0.4321 (2)	0.22920 (18)	0.72142 (15)	0.0196 (4)
H26	0.369289	0.277178	0.773599	0.023*
C41	0.1186 (2)	0.56933 (17)	0.83873 (13)	0.0168 (3)
H41A	0.028885	0.565648	0.901657	0.020*
H41B	0.154483	0.477288	0.826726	0.020*
C42	0.2731 (2)	0.61664 (16)	0.87166 (13)	0.0156 (3)
C43	0.2751 (2)	0.64585 (19)	0.97709 (14)	0.0211 (4)
H43	0.178950	0.633073	1.029618	0.025*
C44	0.4148 (2)	0.6933 (2)	1.00732 (15)	0.0233 (4)
H44	0.414927	0.712340	1.079870	0.028*
C45	0.5537 (2)	0.71247 (18)	0.92981 (14)	0.0181 (3)
C46	0.5572 (2)	0.68223 (18)	0.82470 (14)	0.0193 (4)
H46	0.654034	0.694552	0.772674	0.023*
C47	0.4183 (2)	0.63407 (18)	0.79668 (14)	0.0188 (4)
H47	0.420844	0.612183	0.725051	0.023*
C51	−0.0111 (2)	0.78413 (17)	0.45384 (14)	0.0149 (3)
O1	−0.09068 (17)	0.84261 (13)	0.52191 (11)	0.0236 (3)
O2	−0.01605 (16)	0.83239 (12)	0.34208 (10)	0.0192 (3)
C52	−0.1173 (2)	0.96538 (18)	0.30497 (16)	0.0223 (4)
H52A	−0.072728	1.031755	0.336200	0.027*
H52B	−0.240921	0.965174	0.330429	0.027*
C53	−0.0980 (3)	0.9991 (2)	0.17738 (19)	0.0398 (5)
H53A	0.024644	1.000756	0.153653	0.060*
H53B	−0.166453	1.087456	0.147478	0.060*
H53C	−0.139638	0.931101	0.148006	0.060*
C61	0.1856 (2)	0.61827 (18)	0.28561 (14)	0.0191 (4)
H61A	0.258952	0.549762	0.251684	0.029*
H61B	0.227356	0.704235	0.257956	0.029*
H61C	0.065310	0.627965	0.264454	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0233 (2)	0.0282 (3)	0.0220 (2)	−0.00532 (18)	−0.00373 (17)	−0.00702 (18)
S1	0.0163 (2)	0.0141 (2)	0.0145 (2)	0.00164 (16)	0.00114 (15)	−0.00572 (15)
N1	0.0145 (6)	0.0135 (7)	0.0160 (6)	−0.0016 (5)	0.0015 (5)	−0.0052 (5)
C2	0.0127 (7)	0.0124 (7)	0.0173 (7)	−0.0020 (6)	0.0001 (6)	−0.0055 (6)
N3	0.0148 (6)	0.0122 (7)	0.0155 (6)	−0.0003 (5)	0.0004 (5)	−0.0052 (5)
C4	0.0130 (7)	0.0124 (7)	0.0150 (7)	−0.0019 (6)	0.0004 (6)	−0.0049 (6)
C5	0.0135 (7)	0.0108 (7)	0.0165 (7)	−0.0016 (6)	0.0002 (6)	−0.0040 (6)
C6	0.0130 (7)	0.0125 (8)	0.0169 (7)	−0.0024 (6)	0.0014 (6)	−0.0045 (6)
C21	0.0145 (7)	0.0130 (8)	0.0201 (8)	−0.0014 (6)	−0.0009 (6)	−0.0059 (6)
C22	0.0198 (8)	0.0148 (8)	0.0211 (8)	0.0010 (6)	0.0019 (6)	−0.0061 (6)
C23	0.0201 (8)	0.0163 (9)	0.0311 (9)	0.0021 (7)	0.0027 (7)	−0.0099 (7)
C24	0.0190 (8)	0.0140 (8)	0.0339 (10)	0.0029 (7)	−0.0060 (7)	−0.0062 (7)
C25	0.0291 (9)	0.0181 (9)	0.0237 (9)	0.0011 (7)	−0.0080 (7)	−0.0035 (7)
C26	0.0220 (8)	0.0153 (8)	0.0217 (8)	0.0017 (7)	−0.0046 (7)	−0.0070 (6)
C41	0.0197 (8)	0.0165 (8)	0.0132 (7)	−0.0016 (6)	0.0028 (6)	−0.0041 (6)
C42	0.0188 (8)	0.0117 (8)	0.0141 (7)	0.0016 (6)	0.0006 (6)	−0.0024 (6)
C43	0.0242 (9)	0.0245 (9)	0.0144 (8)	−0.0045 (7)	0.0036 (6)	−0.0057 (7)
C44	0.0286 (9)	0.0280 (10)	0.0141 (8)	−0.0048 (8)	0.0004 (7)	−0.0067 (7)
C45	0.0187 (8)	0.0172 (8)	0.0176 (8)	−0.0003 (6)	−0.0028 (6)	−0.0041 (6)
C46	0.0191 (8)	0.0207 (9)	0.0170 (8)	−0.0001 (7)	0.0017 (6)	−0.0056 (6)
C47	0.0212 (8)	0.0204 (9)	0.0145 (7)	−0.0013 (7)	0.0039 (6)	−0.0069 (6)
C51	0.0142 (7)	0.0136 (8)	0.0172 (7)	−0.0018 (6)	−0.0023 (6)	−0.0040 (6)
O1	0.0282 (7)	0.0186 (7)	0.0210 (6)	0.0093 (5)	−0.0027 (5)	−0.0077 (5)
O2	0.0235 (6)	0.0127 (6)	0.0178 (6)	0.0031 (5)	−0.0012 (5)	−0.0013 (5)
C52	0.0278 (9)	0.0114 (8)	0.0248 (9)	0.0034 (7)	−0.0057 (7)	−0.0016 (7)
C53	0.0504 (14)	0.0309 (12)	0.0317 (11)	−0.0009 (10)	−0.0072 (10)	0.0030 (9)
C61	0.0243 (8)	0.0181 (8)	0.0141 (7)	−0.0015 (7)	0.0039 (6)	−0.0051 (6)

Geometric parameters (Å, º)

Cl1—C45	1.7488 (19)	C41—H41A	0.9900
S1—C4	1.7672 (16)	C41—H41B	0.9900
S1—C41	1.8234 (18)	C42—C43	1.390 (2)
N1—C2	1.338 (2)	C42—C47	1.402 (2)
N1—C6	1.344 (2)	C43—C44	1.389 (3)
C2—N3	1.337 (2)	C43—H43	0.9500
C2—C21	1.486 (2)	C44—C45	1.385 (2)
N3—C4	1.332 (2)	C44—H44	0.9500
C4—C5	1.419 (2)	C45—C46	1.386 (2)
C5—C6	1.409 (2)	C46—C47	1.377 (3)
C5—C51	1.484 (2)	C46—H46	0.9500
C6—C61	1.505 (2)	C47—H47	0.9500
C21—C26	1.395 (2)	C51—O1	1.207 (2)
C21—C22	1.397 (2)	C51—O2	1.332 (2)
C22—C23	1.391 (2)	O2—C52	1.454 (2)
C22—H22	0.9500	C52—C53	1.507 (3)
C23—C24	1.388 (3)	C52—H52A	0.9900
C23—H23	0.9500	C52—H52B	0.9900
C24—C25	1.391 (3)	C53—H53A	0.9800
C24—H24	0.9500	C53—H53B	0.9800
C25—C26	1.391 (2)	C53—H53C	0.9800
C25—H25	0.9500	C61—H61A	0.9800
C26—H26	0.9500	C61—H61B	0.9800
C41—C42	1.505 (2)	C61—H61C	0.9800
C4—S1—C41	101.87 (8)	C43—C42—C41	120.82 (15)
C2—N1—C6	117.35 (14)	C47—C42—C41	121.16 (15)
N3—C2—N1	125.60 (15)	C44—C43—C42	121.42 (16)
N3—C2—C21	116.55 (14)	C44—C43—H43	119.3
N1—C2—C21	117.85 (14)	C42—C43—H43	119.3
C4—N3—C2	117.84 (14)	C45—C44—C43	118.81 (16)
N3—C4—C5	121.53 (14)	C45—C44—H44	120.6
N3—C4—S1	116.68 (12)	C43—C44—H44	120.6
C5—C4—S1	121.79 (12)	C44—C45—C46	121.25 (17)
C6—C5—C4	115.96 (14)	C44—C45—Cl1	119.22 (14)
C6—C5—C51	125.40 (15)	C46—C45—Cl1	119.53 (13)
C4—C5—C51	118.61 (14)	C47—C46—C45	119.08 (16)
N1—C6—C5	121.71 (15)	C47—C46—H46	120.5
N1—C6—C61	113.95 (14)	C45—C46—H46	120.5
C5—C6—C61	124.33 (15)	C46—C47—C42	121.39 (16)
C26—C21—C22	119.19 (16)	C46—C47—H47	119.3
C26—C21—C2	120.47 (15)	C42—C47—H47	119.3
C22—C21—C2	120.34 (15)	O1—C51—O2	123.30 (15)
C23—C22—C21	120.28 (16)	O1—C51—C5	122.70 (15)
C23—C22—H22	119.9	O2—C51—C5	114.00 (14)
C21—C22—H22	119.9	C51—O2—C52	115.94 (13)
C24—C23—C22	120.05 (16)	O2—C52—C53	105.96 (16)
C24—C23—H23	120.0	O2—C52—H52A	110.5
C22—C23—H23	120.0	C53—C52—H52A	110.5
C23—C24—C25	120.14 (16)	O2—C52—H52B	110.5
C23—C24—H24	119.9	C53—C52—H52B	110.5
C25—C24—H24	119.9	H52A—C52—H52B	108.7
C26—C25—C24	119.75 (17)	C52—C53—H53A	109.5
C26—C25—H25	120.1	C52—C53—H53B	109.5
C24—C25—H25	120.1	H53A—C53—H53B	109.5
C25—C26—C21	120.56 (16)	C52—C53—H53C	109.5
C25—C26—H26	119.7	H53A—C53—H53C	109.5
C21—C26—H26	119.7	H53B—C53—H53C	109.5
C42—C41—S1	112.36 (11)	C6—C61—H61A	109.5
C42—C41—H41A	109.1	C6—C61—H61B	109.5
S1—C41—H41A	109.1	H61A—C61—H61B	109.5
C42—C41—H41B	109.1	C6—C61—H61C	109.5
S1—C41—H41B	109.1	H61A—C61—H61C	109.5
H41A—C41—H41B	107.9	H61B—C61—H61C	109.5
C43—C42—C47	118.02 (16)
C6—N1—C2—N3	−0.9 (2)	C22—C23—C24—C25	0.9 (3)
C6—N1—C2—C21	178.87 (14)	C23—C24—C25—C26	−1.7 (3)
N1—C2—N3—C4	0.2 (2)	C24—C25—C26—C21	1.0 (3)
C21—C2—N3—C4	−179.60 (14)	C22—C21—C26—C25	0.6 (3)
C2—N3—C4—C5	1.1 (2)	C2—C21—C26—C25	−179.54 (16)
C2—N3—C4—S1	−179.46 (12)	C4—S1—C41—C42	95.25 (12)
C41—S1—C4—N3	5.14 (15)	S1—C41—C42—C43	121.93 (15)
C41—S1—C4—C5	−175.37 (14)	S1—C41—C42—C47	−57.33 (19)
N3—C4—C5—C6	−1.5 (2)	C47—C42—C43—C44	1.2 (3)
S1—C4—C5—C6	179.06 (12)	C41—C42—C43—C44	−178.10 (16)
N3—C4—C5—C51	−179.53 (14)	C42—C43—C44—C45	0.4 (3)
S1—C4—C5—C51	1.0 (2)	C43—C44—C45—C46	−1.5 (3)
C2—N1—C6—C5	0.4 (2)	C43—C44—C45—Cl1	179.03 (14)
C2—N1—C6—C61	−179.30 (14)	C44—C45—C46—C47	0.9 (3)
C4—C5—C6—N1	0.7 (2)	Cl1—C45—C46—C47	−179.63 (13)
C51—C5—C6—N1	178.63 (14)	C45—C46—C47—C42	0.8 (3)
C4—C5—C6—C61	−179.61 (15)	C43—C42—C47—C46	−1.8 (3)
C51—C5—C6—C61	−1.7 (3)	C41—C42—C47—C46	177.48 (15)
N3—C2—C21—C26	1.7 (2)	C6—C5—C51—O1	177.72 (16)
N1—C2—C21—C26	−178.08 (15)	C4—C5—C51—O1	−4.4 (2)
N3—C2—C21—C22	−178.47 (15)	C6—C5—C51—O2	−2.6 (2)
N1—C2—C21—C22	1.7 (2)	C4—C5—C51—O2	175.25 (14)
C26—C21—C22—C23	−1.5 (3)	O1—C51—O2—C52	3.1 (2)
C2—C21—C22—C23	178.72 (16)	C5—C51—O2—C52	−176.57 (14)
C21—C22—C23—C24	0.7 (3)	C51—O2—C52—C53	178.11 (16)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C21–C26 ring and Cg3 is the centroid of the C41–C46 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C41—H41B···N3	0.99	2.28	2.807 (2)	112
C23—H23···O1^i	0.95	2.47	3.239 (2)	138
C46—H46···S1^ii	0.95	2.92	3.798 (2)	154
C52—H52A···S1^iii	0.99	3.01	3.857 (2)	144
C52—H52B···Cg2^iv	0.99	2.72	3.600 (2)	148
C53—H53B···Cg3^iii	0.99	2.91	3.878 (2)	169

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

{4-[(4-Chlorobenzyl)sulfanyl]-6-methyl-2-phenylpyrimidin-5-yl}methanol (3)

Crystal data

C19H17ClN2OS	Dx = 1.415 Mg m^−3
Mr = 356.85	Melting point: 402 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.6074 (12) Å	Cell parameters from 2883 reflections
b = 22.882 (8) Å	θ = 3.0–30.6°
c = 31.816 (12) Å	µ = 0.36 mm^−1
β = 92.41 (5)°	T = 100 K
V = 3351.3 (19) Å^3	Needle, colourless
Z = 8	0.60 × 0.05 × 0.04 mm
F(000) = 1488

Data collection

Agilent Xcalibur Ruby diffractometer	6370 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.043
Graphite monochromator	θmax = 30.7°, θmin = 3.0°
Detector resolution: 10.3456 pixels mm^-1	h = −6→4
ω scans	k = −32→29
17748 measured reflections	l = −44→39
9255 independent reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 2.0892P] where P = (Fo^2 + 2Fc^2)/3
9255 reflections	(Δ/σ)max = 0.001
437 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.50 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
N1A	1.2797 (4)	0.40497 (8)	0.20688 (6)	0.0153 (4)
C2A	1.4163 (5)	0.45253 (10)	0.22188 (7)	0.0129 (5)
C21A	1.6360 (5)	0.44446 (10)	0.25683 (7)	0.0123 (5)
C22A	1.7048 (5)	0.38889 (11)	0.27217 (8)	0.0161 (5)
H22A	1.611331	0.355487	0.260122	0.019*
C23A	1.9108 (6)	0.38235 (11)	0.30520 (8)	0.0186 (5)
H23A	1.957166	0.344393	0.315538	0.022*
C24A	2.0483 (6)	0.43067 (11)	0.32307 (8)	0.0185 (5)
H24A	2.187563	0.425978	0.345702	0.022*
C25A	1.9814 (6)	0.48590 (11)	0.30770 (8)	0.0182 (5)
H25A	2.076520	0.519167	0.319660	0.022*
C26A	1.7763 (5)	0.49288 (10)	0.27496 (8)	0.0156 (5)
H26A	1.730908	0.530963	0.264777	0.019*
N3A	1.3764 (4)	0.50756 (8)	0.20742 (6)	0.0131 (4)
C4A	1.1800 (5)	0.51459 (10)	0.17592 (7)	0.0127 (5)
S1A	1.13494 (14)	0.58490 (3)	0.15305 (2)	0.01607 (14)
C41A	1.3585 (5)	0.63154 (10)	0.18778 (8)	0.0159 (5)
H4A1	1.517000	0.607987	0.201204	0.019*
H4A2	1.447804	0.662640	0.170978	0.019*
C42A	1.1818 (5)	0.65921 (10)	0.22154 (8)	0.0148 (5)
C43A	1.1099 (6)	0.62723 (10)	0.25688 (8)	0.0163 (5)
H43A	1.186639	0.589002	0.260908	0.020*
C44A	0.9275 (6)	0.65045 (10)	0.28636 (8)	0.0166 (5)
H44A	0.877617	0.628126	0.310168	0.020*
C45A	0.8193 (5)	0.70661 (11)	0.28060 (8)	0.0161 (5)
Cl1A	0.58490 (15)	0.73533 (3)	0.31691 (2)	0.02209 (15)
C46A	0.8955 (6)	0.74031 (11)	0.24662 (8)	0.0181 (5)
H46A	0.825923	0.779206	0.243423	0.022*
C47A	1.0767 (6)	0.71594 (10)	0.21712 (8)	0.0176 (5)
H47A	1.129113	0.738595	0.193587	0.021*
C5A	1.0148 (5)	0.46799 (10)	0.15884 (7)	0.0134 (5)
C51A	0.7851 (5)	0.47679 (11)	0.12446 (8)	0.0165 (5)
H5A1	0.612098	0.453039	0.130478	0.020*
H5A2	0.725901	0.518380	0.123592	0.020*
O1A	0.8912 (4)	0.46018 (8)	0.08440 (5)	0.0218 (4)
H1A	0.757634	0.443799	0.069996	0.033*
C6A	1.0769 (5)	0.41286 (10)	0.17570 (7)	0.0149 (5)
C61A	0.9228 (6)	0.35882 (10)	0.15999 (9)	0.0214 (6)
H6A1	1.045772	0.324586	0.165828	0.032*
H6A2	0.882165	0.362105	0.129596	0.032*
H6A3	0.739673	0.354478	0.174279	0.032*
N1B	0.2616 (4)	0.82060 (9)	0.55318 (6)	0.0155 (4)
C2B	0.1432 (5)	0.77237 (10)	0.53616 (7)	0.0134 (5)
C21B	−0.0573 (5)	0.73778 (10)	0.56193 (7)	0.0137 (5)
C22B	−0.1400 (6)	0.75839 (11)	0.60104 (8)	0.0175 (5)
H22B	−0.066556	0.794586	0.611548	0.021*
C23B	−0.3303 (6)	0.72573 (11)	0.62456 (8)	0.0188 (5)
H23B	−0.386816	0.739939	0.651052	0.023*
C24B	−0.4376 (6)	0.67283 (11)	0.60970 (8)	0.0201 (6)
H24B	−0.568180	0.650932	0.625831	0.024*
C25B	−0.3536 (6)	0.65194 (11)	0.57117 (8)	0.0210 (6)
H25B	−0.425164	0.615436	0.560980	0.025*
C26B	−0.1651 (6)	0.68428 (11)	0.54745 (8)	0.0194 (5)
H26B	−0.108965	0.669734	0.521033	0.023*
N3B	0.1868 (4)	0.75209 (8)	0.49712 (6)	0.0147 (4)
C4B	0.3716 (5)	0.78215 (10)	0.47415 (7)	0.0148 (5)
S1B	0.42363 (15)	0.75967 (3)	0.42172 (2)	0.01916 (14)
C41B	0.1877 (6)	0.69560 (11)	0.41546 (8)	0.0207 (6)
H4B1	0.035696	0.697400	0.436514	0.025*
H4B2	0.089825	0.696555	0.387169	0.025*
C42B	0.3520 (5)	0.63884 (11)	0.42071 (8)	0.0172 (5)
C43B	0.4411 (6)	0.61849 (12)	0.46044 (8)	0.0240 (6)
H43B	0.390840	0.639991	0.484620	0.029*
C44B	0.6019 (6)	0.56745 (12)	0.46547 (8)	0.0247 (6)
H44B	0.663190	0.554326	0.492748	0.030*
C45B	0.6710 (6)	0.53620 (11)	0.43033 (8)	0.0196 (5)
Cl1B	0.87761 (16)	0.47237 (3)	0.43587 (2)	0.02764 (16)
C46B	0.5797 (6)	0.55399 (11)	0.39039 (8)	0.0227 (6)
H46B	0.623972	0.531325	0.366477	0.027*
C47B	0.4224 (6)	0.60546 (11)	0.38581 (8)	0.0209 (6)
H47B	0.361389	0.618249	0.358430	0.025*
C5B	0.5188 (5)	0.83189 (10)	0.48939 (7)	0.0150 (5)
C51B	0.7409 (5)	0.86372 (11)	0.46451 (8)	0.0182 (5)
H5B1	0.910452	0.874040	0.483181	0.022*
H5B2	0.808888	0.837971	0.441930	0.022*
O1B	0.6163 (4)	0.91572 (9)	0.44639 (7)	0.0322 (5)
H1B	0.744367	0.934335	0.433958	0.048*
C6B	0.4518 (5)	0.85009 (10)	0.52973 (8)	0.0158 (5)
C61B	0.5852 (6)	0.90393 (11)	0.54991 (8)	0.0240 (6)
H6B1	0.466133	0.916813	0.572970	0.036*
H6B2	0.594511	0.935120	0.528900	0.036*
H6B3	0.781808	0.894832	0.560962	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0145 (10)	0.0147 (10)	0.0168 (10)	−0.0003 (9)	−0.0003 (9)	−0.0003 (8)
C2A	0.0104 (11)	0.0170 (11)	0.0113 (11)	0.0012 (10)	0.0026 (9)	−0.0017 (9)
C21A	0.0128 (12)	0.0141 (11)	0.0103 (11)	0.0031 (10)	0.0035 (9)	0.0008 (9)
C22A	0.0160 (12)	0.0158 (12)	0.0164 (12)	0.0012 (10)	0.0006 (10)	0.0001 (9)
C23A	0.0228 (14)	0.0187 (13)	0.0145 (12)	0.0038 (11)	0.0031 (11)	0.0040 (10)
C24A	0.0160 (12)	0.0260 (13)	0.0132 (12)	0.0047 (11)	−0.0016 (10)	0.0010 (10)
C25A	0.0184 (13)	0.0194 (13)	0.0165 (12)	0.0010 (11)	−0.0030 (11)	−0.0014 (10)
C26A	0.0179 (13)	0.0124 (11)	0.0166 (12)	0.0014 (10)	0.0004 (11)	0.0022 (9)
N3A	0.0143 (10)	0.0124 (9)	0.0125 (10)	0.0008 (8)	0.0014 (8)	0.0001 (8)
C4A	0.0120 (11)	0.0153 (11)	0.0109 (11)	0.0026 (10)	0.0037 (9)	−0.0016 (9)
S1A	0.0204 (3)	0.0145 (3)	0.0131 (3)	0.0021 (3)	−0.0023 (2)	0.0011 (2)
C41A	0.0170 (13)	0.0127 (11)	0.0178 (12)	−0.0016 (10)	−0.0002 (10)	0.0004 (9)
C42A	0.0118 (12)	0.0165 (12)	0.0159 (12)	−0.0013 (10)	−0.0027 (10)	0.0004 (9)
C43A	0.0203 (13)	0.0115 (11)	0.0169 (12)	−0.0004 (10)	−0.0019 (11)	0.0001 (9)
C44A	0.0195 (13)	0.0167 (12)	0.0134 (12)	−0.0027 (10)	−0.0019 (10)	0.0017 (9)
C45A	0.0133 (12)	0.0197 (12)	0.0151 (12)	0.0008 (10)	−0.0012 (10)	−0.0044 (10)
Cl1A	0.0239 (3)	0.0224 (3)	0.0203 (3)	−0.0010 (3)	0.0049 (3)	−0.0057 (2)
C46A	0.0194 (13)	0.0150 (12)	0.0196 (12)	0.0025 (11)	−0.0022 (11)	−0.0001 (10)
C47A	0.0203 (13)	0.0160 (12)	0.0163 (12)	0.0000 (11)	−0.0009 (11)	0.0037 (10)
C5A	0.0085 (11)	0.0189 (12)	0.0131 (11)	0.0010 (10)	0.0021 (9)	−0.0030 (9)
C51A	0.0154 (12)	0.0185 (12)	0.0154 (12)	0.0028 (10)	−0.0013 (10)	−0.0047 (10)
O1A	0.0134 (9)	0.0382 (11)	0.0138 (9)	−0.0005 (8)	−0.0005 (7)	−0.0102 (8)
C6A	0.0130 (12)	0.0173 (12)	0.0146 (11)	0.0015 (10)	0.0022 (10)	−0.0021 (10)
C61A	0.0215 (14)	0.0160 (12)	0.0261 (14)	−0.0020 (11)	−0.0051 (12)	−0.0043 (10)
N1B	0.0144 (10)	0.0193 (10)	0.0127 (10)	0.0007 (9)	−0.0006 (8)	0.0017 (8)
C2B	0.0131 (11)	0.0175 (12)	0.0095 (11)	0.0053 (10)	−0.0021 (9)	0.0019 (9)
C21B	0.0110 (11)	0.0182 (12)	0.0116 (11)	0.0038 (10)	−0.0024 (9)	0.0030 (9)
C22B	0.0197 (13)	0.0186 (12)	0.0140 (12)	0.0026 (11)	−0.0007 (10)	0.0024 (10)
C23B	0.0201 (13)	0.0231 (13)	0.0133 (12)	0.0037 (11)	0.0023 (10)	0.0026 (10)
C24B	0.0153 (13)	0.0260 (14)	0.0190 (13)	0.0026 (11)	0.0010 (11)	0.0105 (11)
C25B	0.0215 (14)	0.0206 (13)	0.0208 (13)	−0.0034 (11)	−0.0008 (11)	0.0014 (10)
C26B	0.0200 (14)	0.0241 (13)	0.0143 (12)	0.0001 (11)	0.0020 (11)	−0.0012 (10)
N3B	0.0154 (10)	0.0176 (10)	0.0109 (9)	0.0040 (9)	−0.0009 (8)	0.0007 (8)
C4B	0.0155 (12)	0.0175 (12)	0.0111 (11)	0.0060 (10)	−0.0020 (10)	0.0033 (9)
S1B	0.0248 (3)	0.0217 (3)	0.0112 (3)	0.0045 (3)	0.0030 (3)	0.0010 (2)
C41B	0.0206 (14)	0.0283 (14)	0.0128 (12)	0.0027 (12)	−0.0036 (11)	−0.0024 (10)
C42B	0.0151 (12)	0.0223 (13)	0.0140 (12)	−0.0025 (11)	−0.0009 (10)	0.0013 (10)
C43B	0.0320 (16)	0.0259 (14)	0.0138 (12)	0.0064 (13)	−0.0026 (12)	−0.0030 (10)
C44B	0.0346 (16)	0.0256 (14)	0.0135 (12)	0.0039 (13)	−0.0047 (12)	0.0031 (10)
C45B	0.0208 (13)	0.0151 (12)	0.0226 (13)	−0.0005 (11)	−0.0017 (11)	0.0007 (10)
Cl1B	0.0308 (4)	0.0196 (3)	0.0321 (4)	0.0035 (3)	−0.0021 (3)	0.0001 (3)
C46B	0.0269 (15)	0.0210 (13)	0.0204 (13)	0.0003 (12)	0.0028 (12)	−0.0060 (10)
C47B	0.0260 (14)	0.0249 (13)	0.0118 (12)	−0.0004 (12)	−0.0009 (11)	−0.0009 (10)
C5B	0.0130 (12)	0.0192 (12)	0.0126 (11)	0.0061 (10)	−0.0010 (10)	0.0041 (9)
C51B	0.0126 (12)	0.0254 (13)	0.0166 (12)	0.0033 (11)	−0.0007 (10)	0.0057 (10)
O1B	0.0144 (9)	0.0397 (12)	0.0424 (13)	0.0033 (9)	0.0018 (9)	0.0291 (10)
C6B	0.0118 (12)	0.0185 (12)	0.0167 (12)	0.0020 (10)	−0.0030 (10)	0.0008 (10)
C61B	0.0254 (15)	0.0273 (14)	0.0192 (13)	−0.0072 (12)	0.0014 (12)	−0.0028 (11)

Geometric parameters (Å, º)

N1A—C2A	1.335 (3)	N1B—C2B	1.335 (3)
N1A—C6A	1.346 (3)	N1B—C6B	1.355 (3)
C2A—N3A	1.350 (3)	C2B—N3B	1.349 (3)
C2A—C21A	1.483 (3)	C2B—C21B	1.489 (3)
C21A—C22A	1.394 (3)	C21B—C26B	1.392 (3)
C21A—C26A	1.395 (3)	C21B—C22B	1.398 (3)
C22A—C23A	1.394 (4)	C22B—C23B	1.394 (3)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.385 (4)	C23B—C24B	1.383 (4)
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—C25A	1.385 (3)	C24B—C25B	1.386 (4)
C24A—H24A	0.9500	C24B—H24B	0.9500
C25A—C26A	1.386 (3)	C25B—C26B	1.388 (4)
C25A—H25A	0.9500	C25B—H25B	0.9500
C26A—H26A	0.9500	C26B—H26B	0.9500
N3A—C4A	1.332 (3)	N3B—C4B	1.336 (3)
C4A—C5A	1.406 (3)	C4B—C5B	1.401 (3)
C4A—S1A	1.774 (2)	C4B—S1B	1.772 (3)
S1A—C41A	1.823 (3)	S1B—C41B	1.831 (3)
C41A—C42A	1.514 (3)	C41B—C42B	1.509 (4)
C41A—H4A1	0.9900	C41B—H4B1	0.9900
C41A—H4A2	0.9900	C41B—H4B2	0.9900
C42A—C47A	1.391 (3)	C42B—C43B	1.393 (3)
C42A—C43A	1.393 (3)	C42B—C47B	1.397 (3)
C43A—C44A	1.391 (3)	C43B—C44B	1.389 (4)
C43A—H43A	0.9500	C43B—H43B	0.9500
C44A—C45A	1.388 (3)	C44B—C45B	1.376 (4)
C44A—H44A	0.9500	C44B—H44B	0.9500
C45A—C46A	1.385 (3)	C45B—C46B	1.383 (4)
C45A—Cl1A	1.743 (3)	C45B—Cl1B	1.748 (3)
C46A—C47A	1.398 (3)	C46B—C47B	1.388 (4)
C46A—H46A	0.9500	C46B—H46B	0.9500
C47A—H47A	0.9500	C47B—H47B	0.9500
C5A—C6A	1.396 (3)	C5B—C6B	1.396 (3)
C5A—C51A	1.504 (3)	C5B—C51B	1.508 (3)
C51A—O1A	1.435 (3)	C51B—O1B	1.432 (3)
C51A—H5A1	0.9900	C51B—H5B1	0.9900
C51A—H5A2	0.9900	C51B—H5B2	0.9900
O1A—H1A	0.8400	O1B—H1B	0.8400
C6A—C61A	1.501 (3)	C6B—C61B	1.508 (3)
C61A—H6A1	0.9800	C61B—H6B1	0.9800
C61A—H6A2	0.9800	C61B—H6B2	0.9800
C61A—H6A3	0.9800	C61B—H6B3	0.9800
C2A—N1A—C6A	117.1 (2)	C2B—N1B—C6B	116.8 (2)
N1A—C2A—N3A	125.6 (2)	N1B—C2B—N3B	125.7 (2)
N1A—C2A—C21A	117.6 (2)	N1B—C2B—C21B	117.9 (2)
N3A—C2A—C21A	116.8 (2)	N3B—C2B—C21B	116.4 (2)
C22A—C21A—C26A	119.0 (2)	C26B—C21B—C22B	119.0 (2)
C22A—C21A—C2A	120.9 (2)	C26B—C21B—C2B	120.4 (2)
C26A—C21A—C2A	120.1 (2)	C22B—C21B—C2B	120.6 (2)
C21A—C22A—C23A	120.0 (2)	C23B—C22B—C21B	119.9 (2)
C21A—C22A—H22A	120.0	C23B—C22B—H22B	120.1
C23A—C22A—H22A	120.0	C21B—C22B—H22B	120.1
C24A—C23A—C22A	120.6 (2)	C24B—C23B—C22B	120.6 (2)
C24A—C23A—H23A	119.7	C24B—C23B—H23B	119.7
C22A—C23A—H23A	119.7	C22B—C23B—H23B	119.7
C23A—C24A—C25A	119.5 (2)	C23B—C24B—C25B	119.7 (2)
C23A—C24A—H24A	120.3	C23B—C24B—H24B	120.2
C25A—C24A—H24A	120.3	C25B—C24B—H24B	120.2
C24A—C25A—C26A	120.4 (2)	C24B—C25B—C26B	120.1 (2)
C24A—C25A—H25A	119.8	C24B—C25B—H25B	120.0
C26A—C25A—H25A	119.8	C26B—C25B—H25B	120.0
C25A—C26A—C21A	120.6 (2)	C25B—C26B—C21B	120.8 (2)
C25A—C26A—H26A	119.7	C25B—C26B—H26B	119.6
C21A—C26A—H26A	119.7	C21B—C26B—H26B	119.6
C4A—N3A—C2A	116.6 (2)	C4B—N3B—C2B	116.7 (2)
N3A—C4A—C5A	122.6 (2)	N3B—C4B—C5B	122.6 (2)
N3A—C4A—S1A	118.84 (18)	N3B—C4B—S1B	118.70 (18)
C5A—C4A—S1A	118.50 (19)	C5B—C4B—S1B	118.62 (18)
C4A—S1A—C41A	103.23 (12)	C4B—S1B—C41B	103.39 (12)
C42A—C41A—S1A	111.58 (17)	C42B—C41B—S1B	112.61 (19)
C42A—C41A—H4A1	109.3	C42B—C41B—H4B1	109.1
S1A—C41A—H4A1	109.3	S1B—C41B—H4B1	109.1
C42A—C41A—H4A2	109.3	C42B—C41B—H4B2	109.1
S1A—C41A—H4A2	109.3	S1B—C41B—H4B2	109.1
H4A1—C41A—H4A2	108.0	H4B1—C41B—H4B2	107.8
C47A—C42A—C43A	118.6 (2)	C43B—C42B—C47B	118.0 (2)
C47A—C42A—C41A	120.9 (2)	C43B—C42B—C41B	121.0 (2)
C43A—C42A—C41A	120.4 (2)	C47B—C42B—C41B	121.0 (2)
C44A—C43A—C42A	120.9 (2)	C44B—C43B—C42B	121.4 (2)
C44A—C43A—H43A	119.5	C44B—C43B—H43B	119.3
C42A—C43A—H43A	119.5	C42B—C43B—H43B	119.3
C45A—C44A—C43A	119.3 (2)	C45B—C44B—C43B	119.0 (2)
C45A—C44A—H44A	120.4	C45B—C44B—H44B	120.5
C43A—C44A—H44A	120.4	C43B—C44B—H44B	120.5
C46A—C45A—C44A	121.1 (2)	C44B—C45B—C46B	121.4 (2)
C46A—C45A—Cl1A	119.45 (19)	C44B—C45B—Cl1B	119.7 (2)
C44A—C45A—Cl1A	119.40 (19)	C46B—C45B—Cl1B	118.8 (2)
C45A—C46A—C47A	118.7 (2)	C45B—C46B—C47B	118.9 (2)
C45A—C46A—H46A	120.7	C45B—C46B—H46B	120.5
C47A—C46A—H46A	120.7	C47B—C46B—H46B	120.5
C42A—C47A—C46A	121.3 (2)	C46B—C47B—C42B	121.2 (2)
C42A—C47A—H47A	119.4	C46B—C47B—H47B	119.4
C46A—C47A—H47A	119.4	C42B—C47B—H47B	119.4
C6A—C5A—C4A	116.0 (2)	C6B—C5B—C4B	116.0 (2)
C6A—C5A—C51A	121.8 (2)	C6B—C5B—C51B	121.3 (2)
C4A—C5A—C51A	122.2 (2)	C4B—C5B—C51B	122.7 (2)
O1A—C51A—C5A	110.8 (2)	O1B—C51B—C5B	110.1 (2)
O1A—C51A—H5A1	109.5	O1B—C51B—H5B1	109.6
C5A—C51A—H5A1	109.5	C5B—C51B—H5B1	109.6
O1A—C51A—H5A2	109.5	O1B—C51B—H5B2	109.6
C5A—C51A—H5A2	109.5	C5B—C51B—H5B2	109.6
H5A1—C51A—H5A2	108.1	H5B1—C51B—H5B2	108.2
C51A—O1A—H1A	109.5	C51B—O1B—H1B	109.5
N1A—C6A—C5A	122.0 (2)	N1B—C6B—C5B	122.1 (2)
N1A—C6A—C61A	116.0 (2)	N1B—C6B—C61B	115.7 (2)
C5A—C6A—C61A	122.0 (2)	C5B—C6B—C61B	122.2 (2)
C6A—C61A—H6A1	109.5	C6B—C61B—H6B1	109.5
C6A—C61A—H6A2	109.5	C6B—C61B—H6B2	109.5
H6A1—C61A—H6A2	109.5	H6B1—C61B—H6B2	109.5
C6A—C61A—H6A3	109.5	C6B—C61B—H6B3	109.5
H6A1—C61A—H6A3	109.5	H6B1—C61B—H6B3	109.5
H6A2—C61A—H6A3	109.5	H6B2—C61B—H6B3	109.5
C6A—N1A—C2A—N3A	−2.6 (4)	C6B—N1B—C2B—N3B	−3.1 (4)
C6A—N1A—C2A—C21A	178.8 (2)	C6B—N1B—C2B—C21B	177.5 (2)
N1A—C2A—C21A—C22A	2.5 (3)	N1B—C2B—C21B—C26B	−173.8 (2)
N3A—C2A—C21A—C22A	−176.2 (2)	N3B—C2B—C21B—C26B	6.8 (3)
N1A—C2A—C21A—C26A	−177.2 (2)	N1B—C2B—C21B—C22B	6.1 (3)
N3A—C2A—C21A—C26A	4.1 (3)	N3B—C2B—C21B—C22B	−173.3 (2)
C26A—C21A—C22A—C23A	0.1 (4)	C26B—C21B—C22B—C23B	−0.8 (4)
C2A—C21A—C22A—C23A	−179.6 (2)	C2B—C21B—C22B—C23B	179.3 (2)
C21A—C22A—C23A—C24A	0.1 (4)	C21B—C22B—C23B—C24B	0.3 (4)
C22A—C23A—C24A—C25A	−0.4 (4)	C22B—C23B—C24B—C25B	0.4 (4)
C23A—C24A—C25A—C26A	0.6 (4)	C23B—C24B—C25B—C26B	−0.7 (4)
C24A—C25A—C26A—C21A	−0.4 (4)	C24B—C25B—C26B—C21B	0.2 (4)
C22A—C21A—C26A—C25A	0.1 (4)	C22B—C21B—C26B—C25B	0.5 (4)
C2A—C21A—C26A—C25A	179.8 (2)	C2B—C21B—C26B—C25B	−179.6 (2)
N1A—C2A—N3A—C4A	1.1 (4)	N1B—C2B—N3B—C4B	2.2 (4)
C21A—C2A—N3A—C4A	179.7 (2)	C21B—C2B—N3B—C4B	−178.5 (2)
C2A—N3A—C4A—C5A	1.6 (3)	C2B—N3B—C4B—C5B	0.9 (3)
C2A—N3A—C4A—S1A	−175.69 (16)	C2B—N3B—C4B—S1B	−176.92 (17)
N3A—C4A—S1A—C41A	−8.0 (2)	N3B—C4B—S1B—C41B	−0.8 (2)
C5A—C4A—S1A—C41A	174.58 (19)	C5B—C4B—S1B—C41B	−178.71 (19)
C4A—S1A—C41A—C42A	−93.88 (18)	C4B—S1B—C41B—C42B	−99.22 (19)
S1A—C41A—C42A—C47A	−98.0 (2)	S1B—C41B—C42B—C43B	76.8 (3)
S1A—C41A—C42A—C43A	79.1 (3)	S1B—C41B—C42B—C47B	−102.4 (3)
C47A—C42A—C43A—C44A	2.6 (4)	C47B—C42B—C43B—C44B	1.7 (4)
C41A—C42A—C43A—C44A	−174.6 (2)	C41B—C42B—C43B—C44B	−177.5 (3)
C42A—C43A—C44A—C45A	−0.9 (4)	C42B—C43B—C44B—C45B	−0.7 (4)
C43A—C44A—C45A—C46A	−1.6 (4)	C43B—C44B—C45B—C46B	−1.1 (4)
C43A—C44A—C45A—Cl1A	178.72 (19)	C43B—C44B—C45B—Cl1B	179.1 (2)
C44A—C45A—C46A—C47A	2.2 (4)	C44B—C45B—C46B—C47B	2.0 (4)
Cl1A—C45A—C46A—C47A	−178.09 (19)	Cl1B—C45B—C46B—C47B	−178.3 (2)
C43A—C42A—C47A—C46A	−1.9 (4)	C45B—C46B—C47B—C42B	−0.9 (4)
C41A—C42A—C47A—C46A	175.2 (2)	C43B—C42B—C47B—C46B	−0.9 (4)
C45A—C46A—C47A—C42A	−0.4 (4)	C41B—C42B—C47B—C46B	178.4 (3)
N3A—C4A—C5A—C6A	−2.6 (3)	N3B—C4B—C5B—C6B	−2.7 (4)
S1A—C4A—C5A—C6A	174.73 (17)	S1B—C4B—C5B—C6B	175.17 (18)
N3A—C4A—C5A—C51A	177.5 (2)	N3B—C4B—C5B—C51B	176.2 (2)
S1A—C4A—C5A—C51A	−5.2 (3)	S1B—C4B—C5B—C51B	−6.0 (3)
C6A—C5A—C51A—O1A	−78.6 (3)	C6B—C5B—C51B—O1B	−78.7 (3)
C4A—C5A—C51A—O1A	101.4 (3)	C4B—C5B—C51B—O1B	102.4 (3)
C2A—N1A—C6A—C5A	1.4 (3)	C2B—N1B—C6B—C5B	1.1 (3)
C2A—N1A—C6A—C61A	−178.9 (2)	C2B—N1B—C6B—C61B	−179.2 (2)
C4A—C5A—C6A—N1A	1.0 (3)	C4B—C5B—C6B—N1B	1.6 (4)
C51A—C5A—C6A—N1A	−179.1 (2)	C51B—C5B—C6B—N1B	−177.3 (2)
C4A—C5A—C6A—C61A	−178.7 (2)	C4B—C5B—C6B—C61B	−178.1 (2)
C51A—C5A—C6A—C61A	1.3 (4)	C51B—C5B—C6B—C61B	3.0 (4)

Hydrogen-bond geometry (Å, º)

Cg1A is the centroid of the N1A–C6A ring and Cg1B is the centroid of the N1B–C6B ring.

D—H···A	D—H	H···A	D···A	D—H···A
C41A—H4A1···N3A	0.99	2.40	2.905 (3)	111
C41B—H4B1···N3B	0.99	2.38	2.902 (3)	112
C51A—H5A2···S1A	0.99	2.57	3.070 (3)	111
C51B—H5B2···S1B	0.99	2.58	3.081 (3)	111
O1A—H1A···O1B^i	0.84	1.89	2.696 (3)	160
O1B—H1B···O1A^ii	0.84	1.90	2.707 (3)	162
C51A—H5A1···Cg1A^iii	0.99	2.69	3.433 (3)	132
C51B—H5B1···Cg1B^iv	0.99	2.67	3.356 (3)	127
C61A—H6A1···Cl1A^v	0.98	2.70	3.678 (3)	176

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

4-[(4-Chlorobenzyl)sulfanyl]-5,6-dimethyl-2-phenylpyrimidine (4)

Crystal data

C19H17ClN2S	Dx = 1.363 Mg m^−3
Mr = 340.85	Melting point: 395 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.4729 (8) Å	Cell parameters from 5967 reflections
b = 11.4849 (5) Å	θ = 2.8–28.7°
c = 10.3302 (6) Å	µ = 0.36 mm^−1
β = 104.605 (5)°	T = 100 K
V = 1661.60 (16) Å^3	Block, yellow
Z = 4	0.40 × 0.30 × 0.25 mm
F(000) = 712

Data collection

Agilent Xcalibur Sapphire2, large Be window diffractometer	3997 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3098 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 8.3359 pixels mm^-1	θmax = 28.7°, θmin = 2.8°
ω scans	h = −18→19
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)]	k = −10→15
Tmin = 0.877, Tmax = 0.935	l = −13→13
10788 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1116P)^2] where P = (Fo^2 + 2Fc^2)/3
3997 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.33 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
Cl1	0.43472 (4)	0.14774 (4)	−0.00383 (5)	0.03407 (18)
S1	0.76254 (4)	0.50453 (4)	0.34961 (6)	0.03361 (19)
N1	0.90392 (12)	0.81870 (14)	0.56998 (17)	0.0274 (4)
N3	0.79238 (12)	0.73335 (14)	0.38379 (17)	0.0265 (4)
C2	0.83699 (14)	0.82452 (17)	0.4540 (2)	0.0244 (4)
C4	0.81911 (14)	0.62849 (17)	0.4339 (2)	0.0260 (4)
C5	0.89099 (14)	0.61061 (17)	0.5531 (2)	0.0267 (4)
C6	0.93015 (14)	0.71114 (17)	0.6194 (2)	0.0270 (4)
C21	0.81093 (14)	0.94253 (16)	0.39692 (19)	0.0242 (4)
C22	0.85894 (15)	1.04069 (18)	0.4595 (2)	0.0294 (5)
C23	0.83240 (16)	1.15060 (17)	0.4082 (2)	0.0319 (5)
C24	0.75829 (16)	1.16419 (17)	0.2930 (2)	0.0305 (5)
C25	0.71232 (15)	1.06651 (17)	0.2299 (2)	0.0294 (5)
C26	0.73854 (14)	0.95634 (17)	0.2804 (2)	0.0269 (4)
C41	0.67399 (16)	0.56648 (16)	0.2091 (2)	0.0303 (5)
C42	0.61042 (15)	0.46647 (17)	0.1489 (2)	0.0263 (4)
C43	0.53418 (17)	0.43447 (18)	0.1992 (2)	0.0330 (5)
C44	0.47914 (16)	0.33773 (18)	0.1514 (2)	0.0325 (5)
C45	0.50189 (14)	0.27245 (16)	0.05214 (19)	0.0248 (4)
C46	0.57638 (16)	0.30241 (18)	−0.0030 (2)	0.0310 (5)
C47	0.63007 (16)	0.40024 (18)	0.0466 (2)	0.0308 (5)
C51	0.92119 (17)	0.49118 (17)	0.6061 (2)	0.0334 (5)
C61	1.00389 (16)	0.7053 (2)	0.7501 (2)	0.0355 (5)
H22	0.909910	1.032180	0.537439	0.035*
H23	0.864913	1.217219	0.451726	0.038*
H24	0.739686	1.239650	0.258451	0.037*
H25	0.662148	1.075002	0.151014	0.035*
H26	0.706959	0.889843	0.235170	0.032*
H43	0.519272	0.479892	0.268087	0.040*
H44	0.426720	0.316818	0.186407	0.039*
H46	0.590397	0.257323	−0.072726	0.037*
H47	0.681361	0.422307	0.009786	0.037*
H411	0.705187	0.600462	0.142868	0.036*
H412	0.636736	0.628065	0.240045	0.036*
H511	0.878218	0.463505	0.659217	0.050*
H512	0.918418	0.437797	0.531248	0.050*
H513	0.986651	0.494252	0.662602	0.050*
H611	0.978822	0.660362	0.814363	0.053*
H612	1.061531	0.667446	0.736982	0.053*
H613	1.019586	0.784301	0.784512	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C42	0.0322 (10)	0.0168 (9)	0.0251 (10)	−0.0002 (8)	−0.0016 (8)	0.0010 (7)
C43	0.0439 (13)	0.0245 (11)	0.0319 (11)	0.0010 (9)	0.0121 (10)	−0.0072 (8)
C44	0.0353 (12)	0.0270 (10)	0.0371 (12)	−0.0022 (9)	0.0125 (9)	−0.0016 (9)
C45	0.0317 (10)	0.0171 (9)	0.0208 (9)	−0.0011 (7)	−0.0020 (7)	0.0012 (7)
Cl1	0.0437 (3)	0.0258 (3)	0.0284 (3)	−0.0108 (2)	0.0011 (2)	−0.00198 (19)
C46	0.0399 (12)	0.0266 (10)	0.0267 (11)	−0.0049 (9)	0.0086 (9)	−0.0062 (8)
C47	0.0351 (11)	0.0275 (10)	0.0303 (11)	−0.0059 (9)	0.0094 (9)	−0.0008 (8)
C41	0.0372 (11)	0.0187 (9)	0.0300 (11)	−0.0020 (8)	−0.0012 (9)	−0.0016 (8)
S1	0.0382 (3)	0.0172 (3)	0.0378 (3)	−0.0008 (2)	−0.0045 (2)	−0.0015 (2)
C4	0.0255 (10)	0.0203 (9)	0.0308 (11)	0.0003 (8)	0.0041 (8)	−0.0022 (8)
N3	0.0280 (9)	0.0190 (8)	0.0296 (9)	−0.0014 (7)	0.0020 (7)	−0.0017 (6)
C2	0.0237 (9)	0.0204 (9)	0.0275 (10)	−0.0009 (7)	0.0035 (8)	−0.0005 (8)
N1	0.0274 (9)	0.0221 (8)	0.0288 (9)	−0.0014 (7)	0.0001 (7)	0.0018 (7)
C6	0.0261 (10)	0.0226 (10)	0.0301 (10)	−0.0010 (8)	0.0030 (8)	0.0027 (8)
C5	0.0256 (10)	0.0240 (10)	0.0297 (10)	0.0004 (8)	0.0055 (8)	0.0033 (8)
C61	0.0376 (12)	0.0286 (11)	0.0327 (12)	−0.0023 (9)	−0.0052 (9)	0.0035 (9)
C51	0.0373 (12)	0.0227 (10)	0.0377 (13)	0.0050 (8)	0.0047 (10)	0.0041 (8)
C21	0.0262 (10)	0.0181 (9)	0.0265 (10)	−0.0013 (7)	0.0035 (8)	−0.0011 (7)
C26	0.0269 (10)	0.0205 (9)	0.0298 (11)	−0.0021 (8)	0.0008 (8)	−0.0018 (8)
C25	0.0299 (10)	0.0251 (10)	0.0289 (11)	0.0010 (8)	−0.0003 (8)	0.0024 (8)
C24	0.0366 (12)	0.0204 (9)	0.0332 (11)	0.0020 (8)	0.0065 (9)	0.0037 (8)
C23	0.0372 (12)	0.0202 (10)	0.0348 (12)	−0.0048 (8)	0.0025 (9)	−0.0023 (8)
C22	0.0307 (10)	0.0226 (10)	0.0304 (11)	−0.0051 (8)	−0.0005 (8)	−0.0027 (8)

Geometric parameters (Å, º)

C42—C43	1.383 (3)	N1—C6	1.354 (2)
C42—C47	1.388 (3)	C6—C5	1.388 (3)
C42—C41	1.505 (3)	C6—C61	1.497 (3)
C43—C44	1.384 (3)	C5—C51	1.501 (3)
C43—H43	0.9500	C61—H613	0.9800
C44—C45	1.375 (3)	C61—H612	0.9800
C44—H44	0.9500	C61—H611	0.9800
C45—C46	1.383 (3)	C51—H513	0.9800
C45—Cl1	1.7457 (19)	C51—H512	0.9800
C46—C47	1.388 (3)	C51—H511	0.9800
C46—H46	0.9500	C21—C26	1.392 (3)
C47—H47	0.9500	C21—C22	1.395 (3)
C41—S1	1.821 (2)	C26—C25	1.384 (3)
C41—H412	0.9900	C26—H26	0.9500
C41—H411	0.9900	C25—C24	1.381 (3)
S1—C4	1.759 (2)	C25—H25	0.9500
C4—N3	1.329 (2)	C24—C23	1.395 (3)
C4—C5	1.412 (3)	C24—H24	0.9500
N3—C2	1.343 (2)	C23—C22	1.385 (3)
C2—N1	1.339 (3)	C23—H23	0.9500
C2—C21	1.488 (3)	C22—H22	0.9500
C43—C42—C47	118.46 (19)	C5—C6—C61	121.15 (18)
C43—C42—C41	120.66 (19)	C6—C5—C4	115.37 (18)
C47—C42—C41	120.8 (2)	C6—C5—C51	122.34 (19)
C42—C43—C44	121.42 (19)	C4—C5—C51	122.28 (19)
C42—C43—H43	119.3	C6—C61—H613	109.5
C44—C43—H43	119.3	C6—C61—H612	109.5
C45—C44—C43	118.64 (19)	H613—C61—H612	109.5
C45—C44—H44	120.7	C6—C61—H611	109.5
C43—C44—H44	120.7	H613—C61—H611	109.5
C44—C45—C46	121.94 (18)	H612—C61—H611	109.5
C44—C45—Cl1	118.43 (16)	C5—C51—H513	109.5
C46—C45—Cl1	119.63 (15)	C5—C51—H512	109.5
C45—C46—C47	118.11 (19)	H513—C51—H512	109.5
C45—C46—H46	120.9	C5—C51—H511	109.5
C47—C46—H46	120.9	H513—C51—H511	109.5
C42—C47—C46	121.4 (2)	H512—C51—H511	109.5
C42—C47—H47	119.3	C26—C21—C22	119.16 (18)
C46—C47—H47	119.3	C26—C21—C2	120.47 (17)
C42—C41—S1	105.39 (13)	C22—C21—C2	120.37 (18)
C42—C41—H412	110.7	C25—C26—C21	120.33 (19)
S1—C41—H412	110.7	C25—C26—H26	119.8
C42—C41—H411	110.7	C21—C26—H26	119.8
S1—C41—H411	110.7	C24—C25—C26	120.73 (19)
H412—C41—H411	108.8	C24—C25—H25	119.6
C4—S1—C41	102.96 (9)	C26—C25—H25	119.6
N3—C4—C5	123.31 (18)	C25—C24—C23	119.13 (19)
N3—C4—S1	119.16 (15)	C25—C24—H24	120.4
C5—C4—S1	117.53 (15)	C23—C24—H24	120.4
C4—N3—C2	116.31 (17)	C22—C23—C24	120.50 (19)
N1—C2—N3	125.82 (18)	C22—C23—H23	119.7
N1—C2—C21	117.00 (17)	C24—C23—H23	119.7
N3—C2—C21	117.17 (17)	C23—C22—C21	120.1 (2)
C2—N1—C6	116.97 (17)	C23—C22—H22	119.9
N1—C6—C5	122.16 (19)	C21—C22—H22	119.9
N1—C6—C61	116.69 (18)
C47—C42—C43—C44	1.1 (3)	C2—N1—C6—C61	−179.07 (18)
C41—C42—C43—C44	−175.33 (19)	N1—C6—C5—C4	−2.6 (3)
C42—C43—C44—C45	0.3 (3)	C61—C6—C5—C4	177.25 (19)
C43—C44—C45—C46	−1.6 (3)	N1—C6—C5—C51	178.82 (19)
C43—C44—C45—Cl1	177.88 (17)	C61—C6—C5—C51	−1.3 (3)
C44—C45—C46—C47	1.3 (3)	N3—C4—C5—C6	2.6 (3)
Cl1—C45—C46—C47	−178.15 (16)	S1—C4—C5—C6	−176.93 (15)
C43—C42—C47—C46	−1.4 (3)	N3—C4—C5—C51	−178.8 (2)
C41—C42—C47—C46	175.0 (2)	S1—C4—C5—C51	1.6 (3)
C45—C46—C47—C42	0.2 (3)	N1—C2—C21—C26	−176.66 (19)
C43—C42—C41—S1	85.1 (2)	N3—C2—C21—C26	4.3 (3)
C47—C42—C41—S1	−91.3 (2)	N1—C2—C21—C22	3.5 (3)
C42—C41—S1—C4	−169.05 (14)	N3—C2—C21—C22	−175.58 (18)
C41—S1—C4—N3	−1.80 (19)	C22—C21—C26—C25	−2.3 (3)
C41—S1—C4—C5	177.79 (16)	C2—C21—C26—C25	177.86 (18)
C5—C4—N3—C2	−0.8 (3)	C21—C26—C25—C24	1.0 (3)
S1—C4—N3—C2	178.79 (14)	C26—C25—C24—C23	0.5 (3)
C4—N3—C2—N1	−1.4 (3)	C25—C24—C23—C22	−0.7 (3)
C4—N3—C2—C21	177.60 (18)	C24—C23—C22—C21	−0.6 (3)
N3—C2—N1—C6	1.3 (3)	C26—C21—C22—C23	2.1 (3)
C21—C2—N1—C6	−177.61 (18)	C2—C21—C22—C23	−178.0 (2)
C2—N1—C6—C5	0.8 (3)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the C21–C26 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···Cl1^i	0.95	2.76	3.502 (2)	135
C47—H47···Cg2^ii	0.95	2.56	3.470 (2)	161
C51—H511···Cg2^iii	0.99	2.61	3.557 (2)	162

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