Multicomponent solid forms of the uric acid reabsorption inhibitor lesinurad and cocrystal polymorphs with urea: DFT simulation and solubility study

Lesinurad (systematic name: 2-{[5-bromo-4-(4-cyclo­propyl­naphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfan­yl}acetic acid, C₁₇H₁₄BrN₃O₂S) is a selective uric acid reabsorption inhibitor related to gout, which exhibits poor aqueous solubility. High-throughput solid-form screening was performed to screen for new solid forms with improved pharmaceutically relevant properties. During polymorph screening, we obtained two solvates with methanol (CH₃OH) and ethanol (C₂H₅OH). Binary systems with caffeine (systematic name: 3,7-di­hydro-1,3,7-trimethyl-1H-purine-2,6-dione, C₈H₁₀N₄O₂) and nicotinamide (C₆H₆N₂O), polymorphs with urea (CH₄N₂O) and eutectics with similar drugs, like allopurinol and febuxostat, were prepared using the crystal engineering approach. All these novel solid forms were confirmed by XRD, DSC and FT–IR. The crystal structures were solved by single-crystal and powder X-ray diffraction. The crystal structures indicate that the lesinurad mol­ecule is highly flexible and the triazole moiety, along with the rotatable thio­acetic acid (side chain) and cyclo­propane ring, is almost perpendicular to the planar naphthalene moiety. The carb­oxy­lic acid–triazole heterosynthon in the drug is inter­rupted by the presence of methanol and ethanol molecules in their crystal structures and forms inter­molecular macrocyclic rings. The caffeine cocrystal maintains the consistency of the acid–triazole heterosynthons as in the drug and, in addition, they are bound by several auxiliary inter­actions. In the binary system of nicotinamide and urea, the acid–triazole heterosynthon is replaced by an acid–amide synthon. Among the urea cocrystal polymorphs, Form I (P, 1:1) consists of an acid–amide (urea) heterodimer, whereas in Form II (P2₁/c, 2:2), both acid–amide heterosynthons and urea–urea dimers co-exist. Density functional theory (DFT) calculations further support the experimentally observed synthon hierarchies in the cocrystals. Aqueous solubility experiments of lesinurad and its binary solids in pH 5 acetate buffer medium indicate the apparent solubility order lesinurad–urea Form I (43-fold) > lesinurad–caffeine (20-fold) > lesinurad–allopurinol (12-fold) ≃ lesinurad–nicotinamide (11-fold) > lesinurad, and this order is correlated with the crystal structures.

Computing details

Data collection: DataCollector (PANalytical, 2010) for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Cell refinement: MRIA (Zlokazov & Chernyshev, 1992) for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Data reduction: DataCollector for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Program(s) used to solve structure: simulated annealing (Zhukov et al., 2001) for LESForm2, LESNAM, LESUREFormI; SHELXT (Sheldrick, 2015a) for LESEtOH. Program(s) used to refine structure: MRIA for LESForm2, LESNAM, LESUREFormI; SHELXL97 (Sheldrick, 2008a) for LESMeOH; SHELXL2016 (Sheldrick, 2015b) for LESEtOH; SHELXL2014 (Sheldrick, 2015b) for LESCAF; olex2.refine (Bourhis et al., 2015) for LESUREFormII. Molecular graphics: Mercury (Macrae et al., 2008) for LESForm2, LESNAM, LESUREFormI; OLEX2 (Dolomanov et al., 2009) for LESEtOH; OLEX2 (Dolomanov et al., 2009) for LESUREFormII. Software used to prepare material for publication: MRIA and SHELXL97 (Sheldrick, 2008a) for LESForm2, LESNAM, LESUREFormI; OLEX2 (Dolomanov et al., 2009) for LESEtOH; OLEX2 (Dolomanov et al., 2009) for LESUREFormII.

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-\ 3-yl]sulfanyl}acetic acid (LESForm2)

Crystal data

C17H14BrN3O2S	F(000) = 1632
Mr = 404.28	Dx = 1.525 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	T = 298 K
a = 22.1247 (17) Å	Particle morphology: needle
b = 8.7081 (8) Å	colorless
c = 18.2738 (15) Å	flat_sheet, 15 × 1 mm
V = 3520.7 (5) Å^3	Specimen preparation: Prepared at 298 K and 101 kPa
Z = 8

Data collection

EMPYREAN (PANanalytical) diffractometer	Data collection mode: reflection
Radiation source: line-focus sealed tube	Scan method: continuous
Curved Germanium (111) monochromator	2θmin = 5.004°, 2θmax = 80.008°, 2θstep = 0.017°
Specimen mounting: thin layer on the non-diffracting silicon plate

Refinement

Refinement on Inet	132 parameters
Least-squares matrix: full with fixed elements per cycle	78 restraints
Rp = 0.032	0 constraints
Rwp = 0.042	H-atom parameters not refined
Rexp = 0.022	Weighting scheme based on measured s.u.'s
RBragg = 0.065	(Δ/σ)max = 0.004
4413 data points	Background function: Chebyshev polynomial up to the 5th order
Excluded region(s): none	Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [010], texture parameter r = 1.09(1).
Profile function: split-type pseudo-Voigt (Toraya, 1986)

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
Br1	0.25630 (6)	0.62021 (15)	0.80770 (8)	0.0641 (7)*
S1	0.47830 (14)	0.4168 (3)	0.91070 (18)	0.0570 (15)*
O1	0.4941 (3)	0.6432 (7)	0.7807 (3)	0.061 (3)*
O2	0.5854 (3)	0.5645 (8)	0.7597 (4)	0.058 (3)*
H2	0.5867	0.6424	0.7345	0.087*
N1	0.3724 (3)	0.5451 (8)	0.8737 (5)	0.060 (4)*
N2	0.3379 (4)	0.3943 (9)	0.7863 (4)	0.062 (4)*
N3	0.3915 (4)	0.3324 (9)	0.8117 (4)	0.059 (4)*
C1	0.3753 (4)	0.6723 (11)	0.9268 (6)	0.062 (5)*
C2	0.3495 (5)	0.6511 (10)	0.9973 (6)	0.070 (5)*
C3	0.3505 (5)	0.7805 (12)	1.0451 (5)	0.066 (5)*
C4	0.3738 (4)	0.9229 (11)	1.0206 (6)	0.061 (5)*
C5	0.4001 (4)	0.9329 (12)	0.9533 (6)	0.064 (5)*
H5	0.4191	1.0238	0.9398	0.077*
C6	0.3993 (4)	0.8072 (12)	0.9028 (6)	0.060 (5)*
H6	0.4145	0.8173	0.8556	0.072*
C7	0.3229 (5)	0.5120 (13)	1.0201 (6)	0.063 (5)*
H7	0.3232	0.4288	0.9881	0.076*
C8	0.2967 (5)	0.4947 (13)	1.0872 (6)	0.068 (5)*
H8	0.2790	0.4027	1.1016	0.082*
C9	0.2981 (5)	0.6264 (11)	1.1342 (8)	0.072 (5)*
H9	0.2814	0.6188	1.1808	0.086*
C10	0.3225 (4)	0.7588 (14)	1.1137 (7)	0.070 (5)*
H10	0.3211	0.8412	1.1461	0.084*
C11	0.3788 (5)	1.0585 (12)	1.0703 (6)	0.060 (5)*
H11	0.3413	1.1020	1.0899	0.072*
C12	0.4313 (4)	1.1643 (11)	1.0604 (6)	0.070 (5)*
H12A	0.4577	1.1462	1.0189	0.084*
H12B	0.4254	1.2716	1.0726	0.084*
C13	0.4336 (4)	1.0553 (10)	1.1202 (6)	0.072 (5)*
H13A	0.4289	1.0947	1.1695	0.086*
H13B	0.4611	0.9691	1.1157	0.086*
C14	0.3271 (5)	0.5148 (13)	0.8249 (6)	0.064 (5)*
C15	0.4120 (4)	0.4269 (11)	0.8627 (7)	0.067 (5)*
C16	0.5328 (5)	0.4103 (11)	0.8358 (6)	0.074 (5)*
H16A	0.5728	0.3935	0.8560	0.089*
H16B	0.5233	0.3237	0.8045	0.089*
C17	0.5338 (5)	0.5543 (12)	0.7900 (6)	0.069 (5)*

Geometric parameters (Å, º)

Br1—C14	1.842 (10)	C5—H5	0.9303
S1—C15	1.711 (11)	C6—H6	0.9299
S1—C16	1.825 (12)	C7—C8	1.366 (15)
O1—C17	1.183 (12)	C7—H7	0.9296
O2—C17	1.272 (12)	C8—C9	1.433 (16)
O2—H2	0.8202	C8—H8	0.9300
N1—C15	1.368 (12)	C9—C10	1.327 (16)
N1—C14	1.367 (13)	C9—H9	0.9298
N1—C1	1.474 (13)	C10—H10	0.9299
N2—C14	1.287 (14)	C11—C12	1.493 (14)
N2—N3	1.383 (11)	C11—C13	1.517 (15)
N3—C15	1.324 (13)	C11—H11	0.9803
C1—C6	1.362 (14)	C12—C13	1.448 (15)
C1—C2	1.421 (15)	C12—H12A	0.9701
C2—C7	1.410 (14)	C12—H12B	0.9702
C2—C3	1.425 (14)	C13—H13A	0.9701
C3—C10	1.412 (15)	C13—H13B	0.9697
C3—C4	1.416 (14)	C16—C17	1.507 (14)
C4—C5	1.363 (15)	C16—H16A	0.9702
C4—C11	1.494 (14)	C16—H16B	0.9702
C5—C6	1.432 (15)
C15—S1—C16	100.6 (5)	C9—C10—H10	118.5
C17—O2—H2	109.5	C3—C10—H10	118.5
C15—N1—C14	103.2 (8)	C12—C11—C4	118.1 (9)
C15—N1—C1	129.4 (8)	C12—C11—C13	57.5 (7)
C14—N1—C1	127.3 (8)	C4—C11—C13	114.2 (8)
C14—N2—N3	107.1 (8)	C12—C11—H11	117.7
C15—N3—N2	106.7 (8)	C4—C11—H11	117.6
C6—C1—C2	124.1 (9)	C13—C11—H11	117.7
C6—C1—N1	116.9 (9)	C13—C12—C11	62.1 (7)
C2—C1—N1	118.8 (8)	C13—C12—H12A	117.6
C7—C2—C1	123.1 (9)	C11—C12—H12A	117.6
C7—C2—C3	120.3 (10)	C13—C12—H12B	117.6
C1—C2—C3	116.5 (9)	C11—C12—H12B	117.6
C10—C3—C4	123.9 (10)	H12A—C12—H12B	114.6
C10—C3—C2	115.6 (10)	C12—C13—C11	60.4 (7)
C4—C3—C2	120.3 (9)	C12—C13—H13A	117.7
C5—C4—C3	119.8 (9)	C11—C13—H13A	117.7
C5—C4—C11	117.8 (9)	C12—C13—H13B	117.7
C3—C4—C11	121.8 (9)	C11—C13—H13B	117.7
C4—C5—C6	121.8 (9)	H13A—C13—H13B	114.9
C4—C5—H5	119.1	N2—C14—N1	112.3 (9)
C6—C5—H5	119.1	N2—C14—Br1	118.1 (8)
C1—C6—C5	117.2 (10)	N1—C14—Br1	129.7 (8)
C1—C6—H6	121.4	N3—C15—N1	110.6 (9)
C5—C6—H6	121.4	N3—C15—S1	128.6 (8)
C8—C7—C2	122.5 (10)	N1—C15—S1	120.9 (8)
C8—C7—H7	118.7	C17—C16—S1	113.6 (7)
C2—C7—H7	118.8	C17—C16—H16A	108.9
C7—C8—C9	116.2 (10)	S1—C16—H16A	108.9
C7—C8—H8	121.9	C17—C16—H16B	108.9
C9—C8—H8	121.9	S1—C16—H16B	108.9
C10—C9—C8	122.3 (12)	H16A—C16—H16B	107.7
C10—C9—H9	118.9	O1—C17—O2	123.9 (10)
C8—C9—H9	118.8	O1—C17—C16	127.8 (10)
C9—C10—C3	123.1 (11)	O2—C17—C16	108.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3^i	0.82	1.92	2.721 (10)	166
C16—H16B···O1^ii	0.97	2.25	3.209 (12)	172

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

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-\ 3-yl]sulfanyl}acetic acid methanol monosolvate (LESMeOH)

Crystal data

C17H14BrN3O2S·CH4O	Z = 2
Mr = 436.33	F(000) = 444
Triclinic, P1	Dx = 1.535 Mg m^−3
a = 9.0092 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2165 (10) Å	Cell parameters from 8298 reflections
c = 11.6947 (13) Å	θ = 3.1–27.5°
α = 80.899 (6)°	µ = 2.31 mm^−1
β = 79.931 (6)°	T = 298 K
γ = 88.024 (6)°	Block, colorless
V = 944.03 (18) Å^3	0.24 × 0.20 × 0.20 mm

Data collection

XtaLABmini diffractometer	4311 independent reflections
Radiation source: fine-focus sealed tube	3038 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −11→11
Tmin = 0.593, Tmax = 1.000	k = −11→11
10109 measured reflections	l = −15→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.9973P] where P = (Fo^2 + 2Fc^2)/3
4311 reflections	(Δ/σ)max = 0.063
296 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −0.86 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
C50	0.6036 (5)	0.4240 (5)	0.1837 (5)	0.0761 (14)
H50A	0.6282	0.3496	0.2449	0.114*
H50B	0.5182	0.3932	0.1548	0.114*
H50C	0.5797	0.5142	0.2144	0.114*
O10	0.7258 (3)	0.4455 (3)	0.0926 (3)	0.0561 (7)
H1O	1.089 (6)	0.550 (6)	−0.132 (5)	0.086 (18)*
H2	0.513 (4)	−0.009 (4)	−0.247 (3)	0.036 (9)*
H3	0.531 (4)	−0.126 (4)	−0.404 (3)	0.035 (9)*
H6	1.022 (4)	−0.258 (4)	−0.502 (3)	0.042 (10)*
H7	1.239 (5)	−0.222 (5)	−0.440 (4)	0.065 (12)*
H8	1.218 (5)	−0.099 (5)	−0.284 (4)	0.066 (14)*
H9	1.004 (4)	−0.007 (4)	−0.190 (3)	0.046 (10)*
H10O	0.730 (6)	0.380 (6)	0.048 (5)	0.096 (18)*
H11	0.832 (4)	−0.238 (4)	−0.593 (3)	0.050 (11)*
H12A	0.628 (5)	−0.259 (5)	−0.676 (4)	0.075 (14)*
H12B	0.526 (6)	−0.234 (6)	−0.563 (5)	0.091 (18)*
H13A	0.626 (5)	−0.428 (5)	−0.454 (4)	0.076 (15)*
H13B	0.739 (6)	−0.476 (7)	−0.572 (5)	0.112 (19)*
H15A	0.741 (4)	0.501 (4)	−0.153 (3)	0.038 (9)*
H15B	0.806 (5)	0.541 (5)	−0.274 (4)	0.069 (14)*
C1	0.7317 (4)	−0.0283 (3)	−0.2432 (3)	0.0336 (7)
C2	0.6032 (4)	−0.0459 (4)	−0.2846 (3)	0.0406 (8)
C3	0.6103 (4)	−0.1160 (4)	−0.3834 (3)	0.0420 (8)
C4	0.7411 (4)	−0.1703 (3)	−0.4382 (3)	0.0349 (7)
C5	0.8772 (4)	−0.1532 (3)	−0.3939 (3)	0.0328 (7)
C6	1.0180 (4)	−0.2066 (4)	−0.4455 (3)	0.0442 (8)
C7	1.1459 (5)	−0.1867 (5)	−0.4028 (4)	0.0539 (10)
C8	1.1411 (5)	−0.1131 (5)	−0.3068 (4)	0.0540 (10)
C9	1.0083 (4)	−0.0597 (4)	−0.2545 (3)	0.0420 (8)
C10	0.8732 (3)	−0.0790 (3)	−0.2962 (3)	0.0315 (6)
C11	0.7465 (5)	−0.2486 (4)	−0.5411 (3)	0.0442 (8)
C12	0.6126 (7)	−0.2750 (6)	−0.5926 (5)	0.0686 (13)
C13	0.6816 (7)	−0.3982 (5)	−0.5269 (5)	0.0692 (13)
C14	0.7160 (4)	−0.0164 (4)	−0.0261 (3)	0.0450 (8)
C15	0.7298 (4)	0.1915 (4)	−0.1413 (3)	0.0377 (7)
C16	0.8088 (5)	0.4727 (4)	−0.2207 (4)	0.0488 (9)
C17	0.9691 (4)	0.4561 (4)	−0.1991 (3)	0.0487 (9)
N1	0.7245 (3)	0.0443 (3)	−0.1420 (2)	0.0347 (6)
N2	0.7153 (4)	0.0826 (4)	0.0401 (3)	0.0540 (8)
N3	0.7241 (4)	0.2187 (3)	−0.0341 (3)	0.0497 (8)
O1	0.9965 (4)	0.5531 (3)	−0.1372 (3)	0.0678 (9)
O2	1.0564 (4)	0.3668 (5)	−0.2325 (4)	0.0966 (13)
S1	0.74005 (12)	0.31669 (10)	−0.27007 (8)	0.0485 (2)
Br1	0.70985 (6)	−0.21732 (5)	0.02152 (4)	0.06994 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C50	0.065 (3)	0.069 (3)	0.089 (4)	−0.006 (2)	0.014 (3)	−0.027 (3)
O10	0.0597 (18)	0.0557 (17)	0.0564 (17)	−0.0125 (13)	−0.0029 (13)	−0.0245 (13)
C1	0.0428 (19)	0.0292 (15)	0.0290 (15)	−0.0032 (13)	−0.0043 (13)	−0.0069 (12)
C2	0.0373 (19)	0.048 (2)	0.0388 (18)	0.0004 (15)	−0.0055 (15)	−0.0144 (15)
C3	0.037 (2)	0.053 (2)	0.0410 (19)	−0.0098 (16)	−0.0138 (16)	−0.0133 (15)
C4	0.0431 (19)	0.0337 (16)	0.0286 (15)	−0.0081 (14)	−0.0051 (13)	−0.0063 (12)
C5	0.0405 (18)	0.0257 (15)	0.0313 (16)	−0.0045 (13)	−0.0022 (13)	−0.0047 (11)
C6	0.049 (2)	0.0377 (19)	0.045 (2)	−0.0014 (16)	0.0010 (16)	−0.0137 (15)
C7	0.038 (2)	0.058 (2)	0.063 (3)	0.0051 (18)	−0.0003 (18)	−0.0108 (19)
C8	0.039 (2)	0.060 (3)	0.066 (3)	−0.0036 (18)	−0.017 (2)	−0.011 (2)
C9	0.041 (2)	0.0422 (19)	0.045 (2)	−0.0029 (15)	−0.0130 (16)	−0.0097 (15)
C10	0.0351 (17)	0.0279 (15)	0.0314 (15)	−0.0054 (12)	−0.0056 (13)	−0.0031 (12)
C11	0.054 (2)	0.044 (2)	0.0372 (19)	−0.0083 (16)	−0.0032 (17)	−0.0168 (15)
C12	0.084 (4)	0.083 (3)	0.054 (3)	0.009 (3)	−0.034 (3)	−0.035 (3)
C13	0.113 (4)	0.047 (2)	0.055 (3)	−0.022 (3)	−0.024 (3)	−0.014 (2)
C14	0.055 (2)	0.049 (2)	0.0305 (17)	0.0001 (17)	−0.0072 (15)	−0.0065 (15)
C15	0.0438 (19)	0.0342 (17)	0.0386 (18)	0.0014 (14)	−0.0103 (14)	−0.0126 (13)
C16	0.055 (2)	0.0332 (19)	0.060 (3)	−0.0022 (17)	−0.014 (2)	−0.0061 (18)
C17	0.050 (2)	0.047 (2)	0.048 (2)	−0.0031 (17)	−0.0012 (17)	−0.0123 (16)
N1	0.0444 (16)	0.0328 (14)	0.0287 (13)	−0.0022 (11)	−0.0082 (11)	−0.0078 (10)
N2	0.076 (2)	0.0551 (19)	0.0343 (16)	−0.0005 (16)	−0.0103 (15)	−0.0167 (14)
N3	0.069 (2)	0.0429 (17)	0.0426 (17)	−0.0002 (15)	−0.0134 (15)	−0.0185 (13)
O1	0.0542 (19)	0.067 (2)	0.092 (2)	−0.0058 (15)	−0.0163 (17)	−0.0378 (17)
O2	0.067 (2)	0.127 (3)	0.120 (3)	0.032 (2)	−0.030 (2)	−0.082 (3)
S1	0.0670 (6)	0.0374 (5)	0.0449 (5)	−0.0030 (4)	−0.0204 (4)	−0.0058 (4)
Br1	0.1107 (4)	0.0471 (3)	0.0479 (3)	−0.0046 (2)	−0.0114 (2)	0.00364 (17)

Geometric parameters (Å, º)

C50—O10	1.388 (5)	C11—C12	1.483 (6)
C1—C2	1.355 (5)	C11—C13	1.490 (5)
C1—C10	1.414 (4)	C12—C13	1.452 (7)
C1—N1	1.440 (4)	C14—N2	1.286 (4)
C2—C3	1.401 (5)	C14—N1	1.372 (4)
C3—C4	1.359 (5)	C14—Br1	1.848 (4)
C4—C5	1.434 (4)	C15—N3	1.309 (4)
C4—C11	1.491 (4)	C15—N1	1.360 (4)
C5—C6	1.414 (5)	C15—S1	1.737 (3)
C5—C10	1.417 (4)	C16—C17	1.507 (6)
C6—C7	1.362 (5)	C16—S1	1.798 (4)
C7—C8	1.394 (6)	C17—O2	1.182 (5)
C8—C9	1.359 (6)	C17—O1	1.291 (4)
C9—C10	1.415 (5)	N2—N3	1.404 (4)
C2—C1—C10	122.1 (3)	C13—C11—C4	121.1 (4)
C2—C1—N1	119.1 (3)	C13—C12—C11	61.0 (3)
C10—C1—N1	118.8 (3)	C12—C13—C11	60.5 (3)
C1—C2—C3	119.1 (3)	N2—C14—N1	111.7 (3)
C4—C3—C2	122.5 (3)	N2—C14—Br1	126.5 (3)
C3—C4—C5	118.6 (3)	N1—C14—Br1	121.8 (2)
C3—C4—C11	122.0 (3)	N3—C15—N1	110.6 (3)
C5—C4—C11	119.4 (3)	N3—C15—S1	128.1 (3)
C6—C5—C10	118.0 (3)	N1—C15—S1	121.4 (2)
C6—C5—C4	122.2 (3)	C17—C16—S1	114.1 (3)
C10—C5—C4	119.8 (3)	O2—C17—O1	124.9 (4)
C7—C6—C5	120.9 (3)	O2—C17—C16	125.3 (4)
C6—C7—C8	120.8 (4)	O1—C17—C16	109.8 (3)
C9—C8—C7	120.3 (4)	C15—N1—C14	104.1 (3)
C8—C9—C10	120.5 (3)	C15—N1—C1	126.9 (3)
C1—C10—C9	122.6 (3)	C14—N1—C1	128.9 (3)
C1—C10—C5	117.9 (3)	C14—N2—N3	106.5 (3)
C9—C10—C5	119.5 (3)	C15—N3—N2	107.1 (3)
C12—C11—C13	58.5 (3)	C15—S1—C16	98.94 (18)
C12—C11—C4	124.0 (4)

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-\ 3-yl]sulfanyl}acetic acid ethanol monosolvate (LESEtOH)

Crystal data

C17H14BrN3O2S·C2H6O	F(000) = 920
Mr = 450.35	Dx = 1.515 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.292 (6) Å	Cell parameters from 5384 reflections
b = 7.366 (3) Å	θ = 2.6–33.7°
c = 20.193 (9) Å	µ = 2.21 mm^−1
β = 92.857 (6)°	T = 298 K
V = 1974.6 (15) Å^3	Unknown, colorless
Z = 4	0.30 × 0.20 × 0.16 mm

Data collection

Bruker P4 diffractometer	7427 independent reflections
Graphite monochromator	5089 reflections with I > 2σ(I)
Detector resolution: 13.6612 pixels mm^-1	Rint = 0.090
ω scans	θmax = 33.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −20→20
Tmin = 0.705, Tmax = 1.000	k = −11→11
27732 measured reflections	l = −31→31

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 0.2431P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max < 0.001
7427 reflections	Δρmax = 0.47 e Å^−3
253 parameters	Δρmin = −1.08 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
C18	0.3314 (3)	−0.0865 (7)	0.02307 (19)	0.0603 (11)
H18A	0.272983	−0.067955	−0.006899	0.072*
H18B	0.374089	−0.177230	0.003854	0.072*
C19	0.3882 (4)	0.0879 (8)	0.0323 (3)	0.0717 (13)
H19A	0.414475	0.124160	−0.009131	0.107*
H19B	0.442787	0.071145	0.064645	0.107*
H19C	0.343748	0.180363	0.047240	0.107*
O3	0.3003 (2)	−0.1474 (4)	0.08556 (13)	0.0522 (7)
C3	−0.0229 (2)	0.3128 (4)	−0.10467 (15)	0.0339 (6)
C5	0.1662 (2)	0.3143 (4)	−0.08782 (15)	0.0341 (6)
C4	0.0328 (2)	0.2524 (4)	−0.00459 (16)	0.0341 (6)
C8	0.3655 (2)	0.3465 (5)	−0.12646 (18)	0.0415 (7)
C10	0.2084 (2)	0.1669 (4)	−0.12271 (15)	0.0347 (6)
C11	0.1553 (3)	0.0054 (5)	−0.13743 (17)	0.0431 (7)
H11	0.090727	−0.009759	−0.122554	0.052*
C6	0.2195 (3)	0.4679 (5)	−0.07391 (19)	0.0455 (8)
H6	0.189930	0.563663	−0.051981	0.055*
C9	0.3080 (2)	0.1874 (4)	−0.14386 (16)	0.0369 (6)
C7	0.3197 (3)	0.4816 (5)	−0.0928 (2)	0.0487 (8)
H7	0.355980	0.586321	−0.082071	0.058*
C2	−0.1561 (3)	0.3426 (7)	−0.20609 (19)	0.0559 (10)
H2A	−0.172110	0.216044	−0.198498	0.067*
H2B	−0.194083	0.415013	−0.175956	0.067*
C15	0.4739 (3)	0.3584 (6)	−0.1430 (2)	0.0526 (9)
H15	0.513584	0.251510	−0.129247	0.063*
C14	0.3499 (3)	0.0441 (5)	−0.18076 (18)	0.0496 (8)
H14	0.415133	0.054526	−0.194891	0.060*
C1	−0.1888 (3)	0.3912 (6)	−0.27584 (18)	0.0513 (9)
C13	0.2953 (3)	−0.1084 (6)	−0.1956 (2)	0.0579 (10)
H13	0.323020	−0.199635	−0.220815	0.069*
C12	0.1975 (3)	−0.1293 (5)	−0.1733 (2)	0.0553 (9)
H12	0.161472	−0.235097	−0.182992	0.066*
C17	0.5072 (4)	0.4438 (9)	−0.2042 (3)	0.0862 (17)
H17A	0.561193	0.385489	−0.226812	0.103*
H17B	0.456508	0.502162	−0.233142	0.103*
C16	0.5318 (4)	0.5272 (9)	−0.1410 (4)	0.100 (2)
H16A	0.496717	0.638137	−0.130386	0.120*
H16B	0.601340	0.521533	−0.124061	0.120*
N3	0.0645 (2)	0.2975 (3)	−0.06619 (13)	0.0340 (5)
N1	−0.0650 (2)	0.2395 (4)	−0.00459 (14)	0.0393 (6)
N2	−0.1014 (2)	0.2777 (4)	−0.06951 (13)	0.0393 (6)
O1	−0.1297 (2)	0.5079 (4)	−0.30334 (13)	0.0549 (7)
O2	−0.2634 (3)	0.3316 (7)	−0.30162 (18)	0.1058 (17)
S0AA	−0.02337 (6)	0.37733 (14)	−0.18711 (4)	0.0467 (2)
Br1	0.11792 (3)	0.21793 (5)	0.06975 (2)	0.04423 (13)
H1	−0.166 (4)	0.546 (8)	−0.338 (3)	0.094 (18)*
H3	0.251 (4)	−0.181 (7)	0.086 (2)	0.055 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C18	0.054 (2)	0.087 (3)	0.0402 (19)	−0.010 (2)	0.0061 (16)	−0.0119 (19)
C19	0.062 (3)	0.083 (3)	0.070 (3)	−0.010 (2)	0.005 (2)	0.007 (2)
O3	0.0393 (14)	0.076 (2)	0.0409 (14)	−0.0065 (13)	0.0017 (11)	−0.0067 (12)
C3	0.0318 (14)	0.0391 (17)	0.0308 (14)	0.0038 (11)	0.0021 (11)	0.0008 (11)
C5	0.0293 (13)	0.0422 (17)	0.0312 (14)	0.0024 (11)	0.0055 (11)	−0.0012 (11)
C4	0.0367 (15)	0.0358 (16)	0.0303 (14)	0.0037 (11)	0.0062 (11)	−0.0011 (10)
C8	0.0347 (16)	0.0408 (17)	0.0494 (19)	0.0015 (12)	0.0072 (13)	0.0039 (14)
C10	0.0348 (15)	0.0390 (16)	0.0304 (14)	0.0047 (11)	0.0034 (11)	0.0007 (11)
C11	0.0443 (18)	0.0409 (18)	0.0445 (18)	−0.0018 (13)	0.0048 (14)	−0.0032 (13)
C6	0.0414 (17)	0.0384 (17)	0.057 (2)	0.0005 (13)	0.0111 (15)	−0.0107 (14)
C9	0.0360 (15)	0.0382 (17)	0.0367 (15)	0.0060 (11)	0.0041 (12)	0.0027 (12)
C7	0.0406 (18)	0.0426 (19)	0.064 (2)	−0.0054 (13)	0.0102 (16)	−0.0070 (16)
C2	0.0365 (18)	0.092 (3)	0.0391 (18)	−0.0113 (18)	−0.0009 (14)	0.0156 (18)
C15	0.0346 (17)	0.055 (2)	0.069 (3)	0.0038 (14)	0.0146 (16)	0.0071 (18)
C14	0.049 (2)	0.052 (2)	0.048 (2)	0.0128 (16)	0.0162 (16)	−0.0036 (16)
C1	0.0389 (18)	0.077 (3)	0.0373 (17)	−0.0081 (16)	−0.0013 (14)	0.0103 (16)
C13	0.064 (3)	0.049 (2)	0.061 (2)	0.0141 (18)	0.0073 (19)	−0.0174 (17)
C12	0.061 (2)	0.045 (2)	0.060 (2)	0.0020 (16)	0.0023 (19)	−0.0142 (17)
C17	0.058 (3)	0.109 (5)	0.094 (4)	−0.006 (3)	0.024 (3)	0.029 (3)
C16	0.047 (3)	0.097 (4)	0.158 (6)	−0.029 (3)	0.035 (3)	−0.049 (4)
N3	0.0324 (12)	0.0406 (15)	0.0293 (12)	0.0023 (10)	0.0043 (9)	0.0000 (10)
N1	0.0379 (14)	0.0492 (16)	0.0312 (13)	0.0019 (11)	0.0076 (11)	0.0018 (10)
N2	0.0300 (13)	0.0531 (16)	0.0349 (14)	0.0026 (10)	0.0047 (10)	0.0056 (11)
O1	0.0473 (15)	0.077 (2)	0.0392 (14)	−0.0084 (12)	−0.0052 (11)	0.0173 (12)
O2	0.070 (2)	0.184 (4)	0.061 (2)	−0.064 (3)	−0.0287 (18)	0.041 (2)
S0AA	0.0358 (4)	0.0725 (6)	0.0321 (4)	−0.0019 (4)	0.0029 (3)	0.0102 (4)
Br1	0.0451 (2)	0.0533 (2)	0.03372 (18)	0.00474 (14)	−0.00408 (13)	−0.00126 (13)

Geometric parameters (Å, º)

C18—C19	1.497 (7)	C10—C9	1.420 (4)
C18—O3	1.420 (5)	C11—C12	1.366 (5)
C3—N3	1.370 (4)	C6—C7	1.408 (5)
C3—N2	1.316 (4)	C9—C14	1.421 (5)
C3—S0AA	1.731 (3)	C2—C1	1.497 (5)
C5—C10	1.424 (4)	C2—S0AA	1.805 (4)
C5—C6	1.357 (5)	C15—C17	1.475 (6)
C5—N3	1.445 (4)	C15—C16	1.462 (6)
C4—N3	1.374 (4)	C14—C13	1.363 (6)
C4—N1	1.303 (4)	C1—O1	1.307 (4)
C4—Br1	1.852 (3)	C1—O2	1.181 (5)
C8—C9	1.433 (5)	C13—C12	1.405 (6)
C8—C7	1.365 (5)	C17—C16	1.440 (8)
C8—C15	1.498 (5)	N1—N2	1.403 (4)
C10—C11	1.407 (5)
O3—C18—C19	109.1 (3)	C14—C9—C8	121.2 (3)
N3—C3—S0AA	122.0 (2)	C8—C7—C6	122.3 (3)
N2—C3—N3	110.5 (3)	C1—C2—S0AA	113.6 (3)
N2—C3—S0AA	127.4 (2)	C17—C15—C8	123.0 (4)
C10—C5—N3	118.8 (3)	C16—C15—C8	123.7 (4)
C6—C5—C10	121.6 (3)	C16—C15—C17	58.7 (4)
C6—C5—N3	119.7 (3)	C13—C14—C9	120.7 (3)
N3—C4—Br1	124.4 (2)	O1—C1—C2	113.9 (3)
N1—C4—N3	111.6 (3)	O2—C1—C2	121.6 (4)
N1—C4—Br1	124.0 (2)	O2—C1—O1	124.5 (4)
C9—C8—C15	120.0 (3)	C14—C13—C12	120.7 (3)
C7—C8—C9	118.2 (3)	C11—C12—C13	120.1 (4)
C7—C8—C15	121.7 (3)	C16—C17—C15	60.2 (4)
C11—C10—C5	122.9 (3)	C17—C16—C15	61.1 (3)
C11—C10—C9	119.4 (3)	C3—N3—C5	126.9 (3)
C9—C10—C5	117.6 (3)	C3—N3—C4	104.1 (2)
C12—C11—C10	120.8 (3)	C4—N3—C5	128.9 (3)
C5—C6—C7	119.7 (3)	C4—N1—N2	106.4 (3)
C10—C9—C8	120.5 (3)	C3—N2—N1	107.3 (3)
C10—C9—C14	118.3 (3)	C3—S0AA—C2	97.01 (16)

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-\ 3-yl]sulfanyl}acetic acid–3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (1/1) (LESCAF)

Crystal data

C17H14BrN3O2S·C8H10N4O2	F(000) = 1224
Mr = 598.48	Dx = 1.548 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.1245 (8) Å	Cell parameters from 9049 reflections
b = 6.6975 (3) Å	θ = 2.3–25.0°
c = 25.8260 (13) Å	µ = 1.73 mm^−1
β = 101.045 (2)°	T = 100 K
V = 2567.6 (2) Å^3	Needle, colorless
Z = 4	0.36 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	3978 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	θmax = 25.1°, θmin = 2.3°
Tmin = 0.725, Tmax = 0.813	h = −18→18
50811 measured reflections	k = −7→7
4550 independent reflections	l = −30→30

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 1.9564P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.064	(Δ/σ)max = 0.002
S = 1.05	Δρmax = 0.32 e Å^−3
4550 reflections	Δρmin = −0.37 e Å^−3
380 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
24 restraints	Extinction coefficient: 0.0026 (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	Occ. (<1)
Br1	−0.08457 (2)	0.50120 (3)	0.42784 (2)	0.02481 (8)
S1	0.15757 (3)	0.07735 (7)	0.33567 (2)	0.01130 (11)
O2	0.11198 (9)	0.3122 (2)	0.23544 (6)	0.0181 (3)
O1	0.00443 (9)	0.0971 (2)	0.19952 (5)	0.0191 (3)
O4	0.32277 (9)	0.0085 (2)	0.28471 (6)	0.0210 (3)
N1	0.05026 (10)	0.2933 (2)	0.38752 (5)	0.0101 (3)
N2	−0.08880 (10)	0.2061 (2)	0.35014 (6)	0.0145 (3)
N3	−0.02705 (10)	0.0970 (2)	0.32720 (6)	0.0126 (3)
N5	0.47547 (11)	0.0177 (2)	0.30379 (6)	0.0134 (3)
N4	0.39632 (10)	0.0141 (2)	0.21525 (6)	0.0148 (3)
C17	0.07199 (12)	0.1368 (3)	0.23120 (7)	0.0119 (4)
C2	0.17140 (12)	0.3015 (3)	0.46632 (7)	0.0109 (4)
C15	0.05423 (12)	0.1528 (3)	0.34962 (7)	0.0099 (4)
C6	0.15341 (13)	0.5718 (3)	0.40230 (7)	0.0150 (4)
H6	0.1215	0.6316	0.3709	0.018*
C1	0.12592 (12)	0.3938 (3)	0.41912 (7)	0.0108 (4)
C5	0.22950 (13)	0.6663 (3)	0.43190 (7)	0.0169 (4)
H5	0.2475	0.7918	0.4203	0.020*
C16	0.11882 (12)	−0.0173 (3)	0.26965 (7)	0.0108 (4)
H16A	0.1711	−0.0707	0.2562	0.013*
H16B	0.0768	−0.1294	0.2712	0.013*
C7	0.14070 (13)	0.1205 (3)	0.48548 (7)	0.0154 (4)
H7	0.0889	0.0560	0.4661	0.018*
C10	0.29445 (13)	0.3041 (3)	0.54251 (7)	0.0148 (4)
H10	0.3476	0.3628	0.5621	0.018*
C4	0.27881 (12)	0.5839 (3)	0.47703 (7)	0.0140 (4)
C14	−0.04003 (12)	0.3191 (3)	0.38544 (7)	0.0131 (4)
C8	0.18514 (14)	0.0385 (3)	0.53165 (8)	0.0194 (4)
H8	0.1635	−0.0814	0.5444	0.023*
C18	0.39426 (13)	0.0133 (3)	0.26912 (7)	0.0139 (4)
C3	0.24972 (12)	0.3980 (3)	0.49547 (7)	0.0111 (4)
C9	0.26253 (14)	0.1309 (3)	0.56018 (7)	0.0195 (4)
H9	0.2932	0.0725	0.5921	0.023*
C12	0.39116 (13)	0.8855 (3)	0.49048 (8)	0.0212 (4)
H12A	0.3531	0.9527	0.4600	0.025*
H12B	0.4201	0.9763	0.5190	0.025*
C24	0.47776 (14)	0.0179 (3)	0.36096 (7)	0.0199 (4)
H24A	0.4162	0.0264	0.3675	0.030*
H24B	0.5126	0.1330	0.3770	0.030*
H24C	0.5060	−0.1055	0.3764	0.030*
C11	0.36156 (14)	0.6845 (3)	0.50608 (8)	0.0216 (5)
H11	0.3765	0.6554	0.5448	0.026*
C13	0.44229 (15)	0.7072 (3)	0.47971 (11)	0.0351 (6)
H13A	0.5028	0.6865	0.5016	0.042*
H13B	0.4358	0.6629	0.4426	0.042*
O5	0.46964 (17)	0.0151 (9)	0.14481 (10)	0.0199 (6)	0.857 (2)
C19	0.47475 (13)	0.0159 (3)	0.19330 (8)	0.0143 (3)	0.857 (2)
C20	0.55463 (12)	0.0172 (3)	0.23196 (7)	0.0131 (4)	0.857 (2)
C21	0.55541 (13)	0.0186 (3)	0.28544 (8)	0.0143 (3)	0.857 (2)
N7	0.6382 (3)	0.0231 (11)	0.3154 (2)	0.0181 (9)	0.857 (2)
C22	0.69100 (16)	0.0208 (3)	0.27914 (9)	0.0200 (5)	0.857 (2)
H22	0.7549	0.0212	0.2881	0.024*	0.857 (2)
N6	0.64561 (13)	0.0181 (3)	0.22900 (8)	0.0169 (5)	0.857 (2)
C25	0.68535 (17)	0.0205 (4)	0.18157 (10)	0.0236 (6)	0.857 (2)
H25A	0.6784	0.1537	0.1656	0.035*	0.857 (2)
H25B	0.6547	−0.0779	0.1563	0.035*	0.857 (2)
H25C	0.7495	−0.0127	0.1911	0.035*	0.857 (2)
O5A	0.6289 (18)	0.005 (7)	0.3178 (12)	0.0199 (6)	0.143 (2)
C19A	0.55541 (13)	0.0186 (3)	0.28544 (8)	0.0143 (3)	0.143 (2)
C20A	0.55463 (12)	0.0172 (3)	0.23196 (7)	0.0131 (4)	0.143 (2)
C21A	0.47475 (13)	0.0159 (3)	0.19330 (8)	0.0143 (3)	0.143 (2)
N7A	0.4844 (14)	0.026 (8)	0.1435 (7)	0.0181 (9)	0.143 (2)
C22A	0.5732 (8)	0.010 (2)	0.1500 (5)	0.0200 (5)	0.143 (2)
H22A	0.6032	−0.0017	0.1210	0.024*	0.143 (2)
N6A	0.6184 (7)	0.0095 (18)	0.2006 (4)	0.0169 (5)	0.143 (2)
C25A	0.7161 (8)	0.005 (2)	0.2186 (6)	0.0236 (6)	0.143 (2)
H25D	0.7458	0.0242	0.1884	0.035*	0.143 (2)
H25E	0.7338	−0.1246	0.2351	0.035*	0.143 (2)
H25F	0.7341	0.1116	0.2444	0.035*	0.143 (2)
H1	0.0849 (18)	0.398 (4)	0.2154 (10)	0.039 (7)*
C23	0.30883 (15)	0.0128 (4)	0.17853 (9)	0.0241 (5)
H23A	0.320 (4)	0.013 (9)	0.1432 (9)	0.036*	0.52 (3)
H23B	0.277 (3)	−0.110 (5)	0.181 (2)	0.036*	0.52 (3)
H23C	0.270 (3)	0.110 (6)	0.1900 (19)	0.036*	0.52 (3)
H23D	0.314 (4)	−0.086 (7)	0.1522 (18)	0.036*	0.48 (3)
H23E	0.262 (3)	−0.041 (9)	0.195 (2)	0.036*	0.48 (3)
H23F	0.301 (4)	0.137 (5)	0.159 (2)	0.036*	0.48 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01944 (12)	0.03109 (14)	0.02490 (13)	0.00250 (9)	0.00677 (8)	−0.01601 (9)
S1	0.0087 (2)	0.0139 (2)	0.0102 (2)	0.00115 (17)	−0.00080 (17)	−0.00037 (17)
O2	0.0136 (7)	0.0149 (7)	0.0227 (7)	−0.0018 (6)	−0.0042 (6)	0.0093 (6)
O1	0.0178 (7)	0.0190 (7)	0.0166 (7)	0.0023 (6)	−0.0063 (6)	−0.0033 (6)
O4	0.0119 (7)	0.0274 (8)	0.0249 (8)	−0.0009 (6)	0.0064 (6)	−0.0004 (6)
N1	0.0109 (8)	0.0108 (8)	0.0079 (7)	−0.0010 (6)	0.0001 (6)	−0.0011 (6)
N2	0.0123 (8)	0.0162 (8)	0.0155 (8)	0.0004 (6)	0.0038 (6)	−0.0041 (6)
N3	0.0098 (8)	0.0148 (8)	0.0135 (8)	0.0000 (6)	0.0027 (6)	−0.0038 (6)
N5	0.0129 (8)	0.0154 (8)	0.0120 (8)	0.0005 (6)	0.0024 (6)	0.0017 (6)
N4	0.0120 (8)	0.0168 (8)	0.0143 (8)	0.0000 (6)	−0.0007 (6)	0.0017 (6)
C17	0.0108 (9)	0.0162 (10)	0.0096 (9)	0.0023 (7)	0.0043 (7)	−0.0018 (7)
C2	0.0116 (9)	0.0123 (9)	0.0089 (8)	0.0014 (7)	0.0024 (7)	−0.0021 (7)
C15	0.0122 (9)	0.0091 (9)	0.0081 (8)	−0.0001 (7)	0.0013 (7)	0.0008 (7)
C6	0.0183 (10)	0.0156 (9)	0.0093 (9)	−0.0014 (8)	−0.0017 (7)	0.0017 (7)
C1	0.0108 (9)	0.0125 (10)	0.0084 (8)	−0.0004 (7)	−0.0002 (7)	−0.0040 (7)
C5	0.0202 (10)	0.0148 (10)	0.0145 (10)	−0.0066 (8)	0.0008 (8)	0.0014 (7)
C16	0.0109 (9)	0.0111 (9)	0.0100 (9)	0.0001 (7)	0.0008 (7)	−0.0032 (7)
C7	0.0178 (10)	0.0145 (10)	0.0136 (9)	−0.0019 (8)	0.0021 (8)	−0.0014 (7)
C10	0.0132 (10)	0.0203 (10)	0.0100 (9)	0.0030 (8)	−0.0005 (7)	−0.0026 (7)
C4	0.0132 (9)	0.0178 (10)	0.0111 (9)	−0.0020 (8)	0.0023 (7)	−0.0040 (7)
C14	0.0132 (10)	0.0158 (10)	0.0106 (9)	−0.0001 (7)	0.0033 (7)	−0.0030 (7)
C8	0.0277 (11)	0.0146 (10)	0.0162 (10)	−0.0004 (8)	0.0049 (8)	0.0046 (8)
C18	0.0139 (10)	0.0098 (9)	0.0178 (10)	0.0008 (7)	0.0026 (8)	0.0010 (7)
C3	0.0096 (9)	0.0153 (10)	0.0087 (8)	0.0019 (7)	0.0024 (7)	−0.0039 (7)
C9	0.0235 (11)	0.0218 (11)	0.0116 (9)	0.0080 (9)	−0.0003 (8)	0.0042 (8)
C12	0.0162 (10)	0.0182 (11)	0.0275 (11)	−0.0050 (8)	0.0002 (8)	−0.0049 (9)
C24	0.0210 (11)	0.0261 (11)	0.0128 (10)	−0.0009 (8)	0.0034 (8)	0.0009 (8)
C11	0.0207 (11)	0.0249 (11)	0.0163 (10)	−0.0089 (9)	−0.0041 (8)	0.0023 (8)
C13	0.0175 (11)	0.0222 (12)	0.0667 (17)	−0.0034 (9)	0.0106 (11)	−0.0068 (11)
O5	0.0227 (14)	0.0254 (14)	0.0121 (8)	−0.0019 (16)	0.0049 (8)	0.0008 (7)
C19	0.0148 (7)	0.0089 (7)	0.0184 (7)	0.0003 (5)	0.0015 (6)	0.0017 (5)
C20	0.0128 (9)	0.0103 (9)	0.0169 (10)	0.0012 (7)	0.0043 (7)	0.0010 (7)
C21	0.0148 (7)	0.0089 (7)	0.0184 (7)	0.0003 (5)	0.0015 (6)	0.0017 (5)
N7	0.0111 (15)	0.018 (2)	0.0223 (14)	−0.0006 (12)	−0.0043 (13)	0.0055 (10)
C22	0.0117 (11)	0.0226 (13)	0.0256 (13)	0.0027 (9)	0.0028 (10)	0.0068 (10)
N6	0.0143 (11)	0.0170 (10)	0.0204 (12)	0.0035 (8)	0.0062 (9)	0.0034 (9)
C25	0.0229 (14)	0.0251 (13)	0.0269 (14)	0.0031 (10)	0.0151 (11)	0.0017 (11)
O5A	0.0227 (14)	0.0254 (14)	0.0121 (8)	−0.0019 (16)	0.0049 (8)	0.0008 (7)
C19A	0.0148 (7)	0.0089 (7)	0.0184 (7)	0.0003 (5)	0.0015 (6)	0.0017 (5)
C20A	0.0128 (9)	0.0103 (9)	0.0169 (10)	0.0012 (7)	0.0043 (7)	0.0010 (7)
C21A	0.0148 (7)	0.0089 (7)	0.0184 (7)	0.0003 (5)	0.0015 (6)	0.0017 (5)
N7A	0.0111 (15)	0.018 (2)	0.0223 (14)	−0.0006 (12)	−0.0043 (13)	0.0055 (10)
C22A	0.0117 (11)	0.0226 (13)	0.0256 (13)	0.0027 (9)	0.0028 (10)	0.0068 (10)
N6A	0.0143 (11)	0.0170 (10)	0.0204 (12)	0.0035 (8)	0.0062 (9)	0.0034 (9)
C25A	0.0229 (14)	0.0251 (13)	0.0269 (14)	0.0031 (10)	0.0151 (11)	0.0017 (11)
C23	0.0156 (11)	0.0314 (13)	0.0217 (11)	−0.0026 (9)	−0.0054 (9)	0.0030 (9)

Geometric parameters (Å, º)

Br1—C14	1.8502 (18)	C12—C13	1.478 (3)
S1—C15	1.7447 (18)	C12—C11	1.498 (3)
S1—C16	1.8080 (17)	C12—H12A	0.9900
O2—C17	1.316 (2)	C12—H12B	0.9900
O2—H1	0.83 (3)	C24—H24A	0.9800
O1—C17	1.210 (2)	C24—H24B	0.9800
O4—C18	1.224 (2)	C24—H24C	0.9800
N1—C15	1.367 (2)	C11—C13	1.515 (3)
N1—C14	1.367 (2)	C11—H11	1.0000
N1—C1	1.439 (2)	C13—H13A	0.9900
N2—C14	1.300 (2)	C13—H13B	0.9900
N2—N3	1.403 (2)	O5—C19	1.240 (3)
N3—C15	1.309 (2)	C19—C20	1.412 (3)
N5—C18	1.375 (3)	C20—C21	1.379 (3)
N5—C19A	1.380 (2)	C20—N6	1.393 (3)
N5—C21	1.380 (2)	C21—N7	1.340 (4)
N5—C24	1.470 (2)	N7—C22	1.342 (8)
N4—C18	1.398 (2)	C22—N6	1.345 (3)
N4—C21A	1.409 (2)	C22—H22	0.9500
N4—C19	1.409 (2)	N6—C25	1.464 (3)
N4—C23	1.473 (3)	C25—H25A	0.9800
C17—C16	1.511 (2)	C25—H25B	0.9800
C2—C7	1.421 (3)	C25—H25C	0.9800
C2—C1	1.421 (2)	O5A—C19A	1.259 (18)
C2—C3	1.430 (3)	C19A—C20A	1.379 (3)
C6—C1	1.361 (3)	C20A—N6A	1.374 (10)
C6—C5	1.404 (3)	C20A—C21A	1.412 (3)
C6—H6	0.9500	C21A—N7A	1.325 (18)
C5—C4	1.373 (3)	C21A—C22A	2.027 (11)
C5—H5	0.9500	N7A—C22A	1.326 (19)
C16—H16A	0.9900	C22A—N6A	1.354 (14)
C16—H16B	0.9900	C22A—H22A	0.9500
C7—C8	1.367 (3)	N6A—C25A	1.461 (13)
C7—H7	0.9500	C25A—H25D	0.9800
C10—C9	1.368 (3)	C25A—H25E	0.9800
C10—C3	1.419 (3)	C25A—H25F	0.9800
C10—H10	0.9500	C23—H23A	0.960 (10)
C4—C3	1.432 (3)	C23—H23B	0.962 (10)
C4—C11	1.491 (3)	C23—H23C	0.961 (10)
C8—C9	1.402 (3)	C23—H23D	0.962 (10)
C8—H8	0.9500	C23—H23E	0.960 (10)
C9—H9	0.9500	C23—H23F	0.962 (10)
C15—S1—C16	98.92 (8)	C4—C11—H11	114.9
C17—O2—H1	113.8 (19)	C12—C11—H11	114.9
C15—N1—C14	103.85 (14)	C13—C11—H11	114.9
C15—N1—C1	126.07 (15)	C12—C13—C11	60.06 (14)
C14—N1—C1	129.99 (15)	C12—C13—H13A	117.8
C14—N2—N3	105.38 (14)	C11—C13—H13A	117.8
C15—N3—N2	107.98 (14)	C12—C13—H13B	117.8
C18—N5—C19A	120.57 (16)	C11—C13—H13B	117.8
C18—N5—C21	120.57 (16)	H13A—C13—H13B	114.9
C18—N5—C24	120.02 (16)	O5—C19—N4	120.8 (2)
C19A—N5—C24	119.41 (16)	O5—C19—C20	126.4 (2)
C21—N5—C24	119.41 (16)	N4—C19—C20	112.82 (16)
C18—N4—C21A	125.54 (16)	C21—C20—N6	103.64 (17)
C18—N4—C19	125.54 (16)	C21—C20—C19	123.38 (17)
C18—N4—C23	116.89 (16)	N6—C20—C19	132.98 (18)
C21A—N4—C23	117.56 (16)	N7—C21—C20	114.0 (3)
C19—N4—C23	117.56 (16)	N7—C21—N5	125.8 (3)
O1—C17—O2	124.56 (17)	C20—C21—N5	120.24 (17)
O1—C17—C16	121.56 (17)	C21—N7—C22	102.2 (4)
O2—C17—C16	113.88 (15)	N7—C22—N6	114.2 (2)
C7—C2—C1	122.22 (17)	N7—C22—H22	122.9
C7—C2—C3	119.68 (16)	N6—C22—H22	122.9
C1—C2—C3	118.09 (16)	C22—N6—C20	105.95 (18)
N3—C15—N1	110.31 (15)	C22—N6—C25	126.2 (2)
N3—C15—S1	128.91 (14)	C20—N6—C25	127.9 (2)
N1—C15—S1	120.75 (13)	N6—C25—H25A	109.5
C1—C6—C5	119.32 (17)	N6—C25—H25B	109.5
C1—C6—H6	120.3	H25A—C25—H25B	109.5
C5—C6—H6	120.3	N6—C25—H25C	109.5
C6—C1—C2	121.84 (16)	H25A—C25—H25C	109.5
C6—C1—N1	119.16 (16)	H25B—C25—H25C	109.5
C2—C1—N1	118.97 (16)	O5A—C19A—C20A	120.1 (18)
C4—C5—C6	122.41 (18)	O5A—C19A—N5	119.4 (17)
C4—C5—H5	118.8	C20A—C19A—N5	120.24 (17)
C6—C5—H5	118.8	N6A—C20A—C19A	135.9 (5)
C17—C16—S1	114.00 (12)	N6A—C20A—C21A	100.7 (5)
C17—C16—H16A	108.8	C19A—C20A—C21A	123.38 (17)
S1—C16—H16A	108.8	N7A—C21A—N4	130.5 (9)
C17—C16—H16B	108.8	N7A—C21A—C20A	116.6 (9)
S1—C16—H16B	108.8	N4—C21A—C20A	112.82 (16)
H16A—C16—H16B	107.6	N7A—C21A—C22A	40.2 (9)
C8—C7—C2	120.52 (18)	N4—C21A—C22A	170.3 (4)
C8—C7—H7	119.7	C20A—C21A—C22A	76.7 (3)
C2—C7—H7	119.7	C21A—N7A—C22A	99.7 (13)
C9—C10—C3	121.36 (18)	N7A—C22A—N6A	115.8 (12)
C9—C10—H10	119.3	N7A—C22A—C21A	40.1 (8)
C3—C10—H10	119.3	N6A—C22A—C21A	75.9 (6)
C5—C4—C3	118.69 (17)	N7A—C22A—H22A	122.1
C5—C4—C11	120.83 (18)	N6A—C22A—H22A	122.1
C3—C4—C11	120.47 (16)	C21A—C22A—H22A	161.6
N2—C14—N1	112.46 (15)	C22A—N6A—C20A	106.6 (8)
N2—C14—Br1	125.24 (14)	C22A—N6A—C25A	126.9 (11)
N1—C14—Br1	122.29 (13)	C20A—N6A—C25A	126.5 (10)
C7—C8—C9	120.18 (18)	N6A—C25A—H25D	109.5
C7—C8—H8	119.9	N6A—C25A—H25E	109.5
C9—C8—H8	119.9	H25D—C25A—H25E	109.5
O4—C18—N5	121.44 (17)	N6A—C25A—H25F	109.5
O4—C18—N4	121.12 (17)	H25D—C25A—H25F	109.5
N5—C18—N4	117.44 (16)	H25E—C25A—H25F	109.5
C10—C3—C2	117.46 (17)	N4—C23—H23A	108 (3)
C10—C3—C4	122.92 (17)	N4—C23—H23B	111 (3)
C2—C3—C4	119.60 (16)	H23A—C23—H23B	104 (4)
C10—C9—C8	120.76 (18)	N4—C23—H23C	109 (3)
C10—C9—H9	119.6	H23A—C23—H23C	122 (4)
C8—C9—H9	119.6	H23B—C23—H23C	102 (4)
C13—C12—C11	61.21 (14)	N4—C23—H23D	106 (3)
C13—C12—H12A	117.6	H23A—C23—H23D	43 (4)
C11—C12—H12A	117.6	H23B—C23—H23D	65 (4)
C13—C12—H12B	117.6	H23C—C23—H23D	145 (4)
C11—C12—H12B	117.6	N4—C23—H23E	112 (4)
H12A—C12—H12B	114.8	H23A—C23—H23E	134 (5)
N5—C24—H24A	109.5	H23B—C23—H23E	40 (4)
N5—C24—H24B	109.5	H23C—C23—H23E	65 (4)
H24A—C24—H24B	109.5	H23D—C23—H23E	103 (5)
N5—C24—H24C	109.5	N4—C23—H23F	109 (3)
H24A—C24—H24C	109.5	H23A—C23—H23F	63 (4)
H24B—C24—H24C	109.5	H23B—C23—H23F	139 (5)
C4—C11—C12	122.40 (18)	H23C—C23—H23F	63 (4)
C4—C11—C13	119.35 (18)	H23D—C23—H23F	105 (5)
C12—C11—C13	58.72 (14)	H23E—C23—H23F	121 (5)
C14—N2—N3—C15	−0.72 (19)	C3—C4—C11—C12	−175.73 (17)
N2—N3—C15—N1	1.0 (2)	C5—C4—C11—C13	−64.7 (3)
N2—N3—C15—S1	−177.09 (13)	C3—C4—C11—C13	114.7 (2)
C14—N1—C15—N3	−0.86 (19)	C13—C12—C11—C4	−107.1 (2)
C1—N1—C15—N3	−177.82 (16)	C4—C11—C13—C12	112.2 (2)
C14—N1—C15—S1	177.41 (13)	C18—N4—C19—O5	179.5 (4)
C1—N1—C15—S1	0.4 (2)	C23—N4—C19—O5	−0.5 (4)
C16—S1—C15—N3	20.07 (19)	C18—N4—C19—C20	−0.1 (2)
C16—S1—C15—N1	−157.84 (14)	C23—N4—C19—C20	179.96 (16)
C5—C6—C1—C2	0.8 (3)	O5—C19—C20—C21	179.9 (4)
C5—C6—C1—N1	−177.35 (17)	N4—C19—C20—C21	−0.6 (2)
C7—C2—C1—C6	176.97 (17)	O5—C19—C20—N6	0.1 (5)
C3—C2—C1—C6	−1.9 (3)	N4—C19—C20—N6	179.59 (19)
C7—C2—C1—N1	−4.8 (3)	N6—C20—C21—N7	0.9 (4)
C3—C2—C1—N1	176.25 (15)	C19—C20—C21—N7	−178.9 (4)
C15—N1—C1—C6	92.4 (2)	N6—C20—C21—N5	−179.84 (16)
C14—N1—C1—C6	−83.8 (2)	C19—C20—C21—N5	0.3 (3)
C15—N1—C1—C2	−85.9 (2)	C18—N5—C21—N7	179.8 (4)
C14—N1—C1—C2	98.0 (2)	C24—N5—C21—N7	−1.3 (5)
C1—C6—C5—C4	1.3 (3)	C18—N5—C21—C20	0.7 (3)
O1—C17—C16—S1	−138.28 (15)	C24—N5—C21—C20	179.62 (16)
O2—C17—C16—S1	42.42 (19)	C20—C21—N7—C22	−1.1 (6)
C15—S1—C16—C17	60.03 (14)	N5—C21—N7—C22	179.7 (2)
C1—C2—C7—C8	−178.56 (18)	C21—N7—C22—N6	0.9 (6)
C3—C2—C7—C8	0.3 (3)	N7—C22—N6—C20	−0.4 (4)
C6—C5—C4—C3	−2.1 (3)	N7—C22—N6—C25	178.3 (4)
C6—C5—C4—C11	177.29 (18)	C21—C20—N6—C22	−0.3 (2)
N3—N2—C14—N1	0.2 (2)	C19—C20—N6—C22	179.5 (2)
N3—N2—C14—Br1	178.72 (13)	C21—C20—N6—C25	−178.9 (2)
C15—N1—C14—N2	0.4 (2)	C19—C20—N6—C25	0.9 (4)
C1—N1—C14—N2	177.18 (17)	C18—N5—C19A—O5A	−174 (2)
C15—N1—C14—Br1	−178.20 (13)	C24—N5—C19A—O5A	5 (2)
C1—N1—C14—Br1	−1.4 (3)	C18—N5—C19A—C20A	0.7 (3)
C2—C7—C8—C9	−1.0 (3)	C24—N5—C19A—C20A	179.62 (16)
C19A—N5—C18—O4	178.50 (17)	O5A—C19A—C20A—N6A	−2 (2)
C21—N5—C18—O4	178.50 (17)	N5—C19A—C20A—N6A	−176.8 (8)
C24—N5—C18—O4	−0.4 (3)	O5A—C19A—C20A—C21A	175 (2)
C19A—N5—C18—N4	−1.3 (2)	N5—C19A—C20A—C21A	0.3 (3)
C21—N5—C18—N4	−1.3 (2)	C18—N4—C21A—N7A	−176 (3)
C24—N5—C18—N4	179.78 (16)	C23—N4—C21A—N7A	4 (3)
C21A—N4—C18—O4	−178.81 (17)	C18—N4—C21A—C20A	−0.1 (2)
C19—N4—C18—O4	−178.81 (17)	C23—N4—C21A—C20A	179.96 (16)
C23—N4—C18—O4	1.2 (3)	N6A—C20A—C21A—N7A	−6 (3)
C21A—N4—C18—N5	1.0 (3)	C19A—C20A—C21A—N7A	176 (3)
C19—N4—C18—N5	1.0 (3)	N6A—C20A—C21A—N4	177.3 (5)
C23—N4—C18—N5	−179.01 (16)	C19A—C20A—C21A—N4	−0.6 (2)
C9—C10—C3—C2	−1.8 (3)	N6A—C20A—C21A—C22A	−0.9 (7)
C9—C10—C3—C4	177.12 (17)	C19A—C20A—C21A—C22A	−178.9 (4)
C7—C2—C3—C10	1.1 (2)	N4—C21A—N7A—C22A	−176.5 (10)
C1—C2—C3—C10	180.00 (16)	C20A—C21A—N7A—C22A	7 (4)
C7—C2—C3—C4	−177.91 (16)	C21A—N7A—C22A—N6A	−6 (4)
C1—C2—C3—C4	1.0 (2)	N7A—C22A—N6A—C20A	3 (3)
C5—C4—C3—C10	−177.98 (17)	C21A—C22A—N6A—C20A	−1.0 (7)
C11—C4—C3—C10	2.6 (3)	N7A—C22A—N6A—C25A	−176 (3)
C5—C4—C3—C2	0.9 (3)	C21A—C22A—N6A—C25A	179.7 (14)
C11—C4—C3—C2	−178.49 (17)	C19A—C20A—N6A—C22A	179.0 (7)
C3—C10—C9—C8	1.2 (3)	C21A—C20A—N6A—C22A	1.4 (10)
C7—C8—C9—C10	0.3 (3)	C19A—C20A—N6A—C25A	−1.8 (17)
C5—C4—C11—C12	4.9 (3)	C21A—C20A—N6A—C25A	−179.3 (12)

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid–nicotinamide (1/1) (LESNAM)

Crystal data

C17H14BrN3O2S·C6H6N2O	Z = 4
Mr = 526.41	F(000) = 1072
Monoclinic, P21/c	Dx = 1.542 Mg m^−3
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 14.0851 (14) Å	T = 298 K
b = 6.9721 (7) Å	Particle morphology: needle
c = 23.1952 (19) Å	colorless
β = 95.476 (15)°	flat_sheet, 15 × 1 mm
V = 2267.4 (4) Å^3	Specimen preparation: Prepared at 298 K and 101 kPa

Data collection

EMPYREAN (PANanalytical) diffractometer	Data collection mode: reflection
Radiation source: line-focus sealed tube	Scan method: continuous
Curved Germanium (111) monochromator	2θmin = 5.003°, 2θmax = 80.007°, 2θstep = 0.017°
Specimen mounting: thin layer on the non-diffracting silicon plate

Refinement

Refinement on Inet	167 parameters
Least-squares matrix: full with fixed elements per cycle	99 restraints
Rp = 0.036	0 constraints
Rwp = 0.051	H-atom parameters not refined
Rexp = 0.021	Weighting scheme based on measured s.u.'s
RBragg = 0.073	(Δ/σ)max = 0.004
4413 data points	Background function: Chebyshev polynomial up to the 5th order
Excluded region(s): none	Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [100], texture parameter r = 0.84(1).
Profile function: split-type pseudo-Voigt (Toraya, 1986)

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
Br1	0.37370 (10)	0.1272 (4)	−0.03870 (9)	0.0610 (11)*
S1	0.2391 (3)	0.2821 (7)	0.1718 (2)	0.055 (3)*
O1	0.1483 (5)	0.3472 (14)	0.2726 (4)	0.058 (5)*
O2	0.0012 (6)	0.3451 (16)	0.2357 (4)	0.053 (5)*
H2	−0.0074	0.3682	0.2695	0.079*
N1	0.3270 (6)	0.2150 (16)	0.0755 (5)	0.061 (7)*
N2	0.2049 (7)	0.1883 (17)	0.0084 (5)	0.064 (7)*
N3	0.1702 (7)	0.2236 (17)	0.0616 (6)	0.059 (6)*
C1	0.4264 (8)	0.226 (2)	0.1017 (6)	0.063 (9)*
C2	0.4661 (8)	0.070 (2)	0.1353 (6)	0.060 (7)*
C3	0.5624 (7)	0.088 (2)	0.1590 (6)	0.059 (7)*
C4	0.6159 (8)	0.260 (2)	0.1491 (6)	0.065 (8)*
C5	0.5737 (7)	0.399 (3)	0.1159 (6)	0.067 (8)*
H5	0.6086	0.5084	0.1085	0.080*
C6	0.4761 (9)	0.385 (2)	0.0914 (6)	0.072 (8)*
H6	0.4480	0.4838	0.0689	0.086*
C7	0.4143 (7)	−0.096 (3)	0.1470 (6)	0.066 (8)*
H7	0.3507	−0.1065	0.1325	0.079*
C8	0.4566 (9)	−0.242 (2)	0.1796 (6)	0.071 (9)*
H8	0.4225	−0.3531	0.1857	0.085*
C9	0.5503 (9)	−0.224 (2)	0.2036 (6)	0.063 (9)*
H9	0.5776	−0.3214	0.2272	0.076*
C10	0.6032 (7)	−0.065 (2)	0.1930 (5)	0.062 (8)*
H10	0.6666	−0.0574	0.2083	0.074*
C11	0.7161 (9)	0.272 (2)	0.1729 (6)	0.066 (9)*
H11	0.7521	0.1546	0.1670	0.079*
C12	0.7491 (9)	0.372 (2)	0.2265 (6)	0.072 (8)*
H12A	0.7025	0.4436	0.2460	0.086*
H12B	0.7995	0.3130	0.2519	0.086*
C13	0.7728 (9)	0.442 (3)	0.1710 (6)	0.075 (8)*
H13A	0.7413	0.5582	0.1560	0.090*
H13B	0.8382	0.4278	0.1619	0.090*
C14	0.2962 (9)	0.185 (2)	0.0182 (6)	0.065 (8)*
C15	0.2449 (10)	0.237 (2)	0.0997 (7)	0.069 (9)*
C16	0.1090 (8)	0.291 (2)	0.1709 (6)	0.076 (9)*
H16A	0.0826	0.3907	0.1451	0.091*
H16B	0.0809	0.1689	0.1584	0.091*
C17	0.0909 (8)	0.332 (2)	0.2309 (6)	0.071 (8)*
O3	−0.0614 (6)	0.2835 (13)	0.3322 (4)	0.055 (5)*
N4	0.0712 (6)	0.3115 (17)	0.3925 (5)	0.058 (7)*
H4A	0.1052	0.3314	0.3642	0.070*
H4B	0.0976	0.3104	0.4275	0.070*
N5	−0.2345 (8)	0.2092 (16)	0.4621 (5)	0.062 (7)*
C18	−0.0245 (10)	0.282 (2)	0.3819 (6)	0.067 (8)*
C19	−0.0829 (8)	0.258 (2)	0.4301 (7)	0.061 (9)*
C20	−0.1820 (9)	0.234 (2)	0.4199 (7)	0.065 (8)*
H20	−0.2105	0.2348	0.3820	0.078*
C21	−0.1972 (9)	0.199 (2)	0.5166 (6)	0.071 (9)*
H21	−0.2365	0.1752	0.5458	0.085*
C22	−0.0998 (8)	0.225 (2)	0.5307 (7)	0.074 (9)*
H22	−0.0746	0.2247	0.5693	0.089*
C23	−0.0406 (10)	0.2501 (19)	0.4871 (7)	0.070 (9)*
H23	0.0251	0.2616	0.4954	0.084*

Geometric parameters (Å, º)

Br1—C14	1.836 (14)	C9—H9	0.9299
S1—C15	1.712 (16)	C10—H10	0.9300
S1—C16	1.832 (12)	C11—C13	1.43 (2)
O1—C17	1.205 (15)	C11—C12	1.46 (2)
O2—C17	1.282 (14)	C11—H11	0.9797
O2—H2	0.8200	C12—C13	1.44 (2)
N1—C15	1.341 (18)	C12—H12A	0.9703
N1—C14	1.374 (18)	C12—H12B	0.9700
N1—C1	1.474 (15)	C13—H13A	0.9701
N2—C14	1.285 (15)	C13—H13B	0.9701
N2—N3	1.392 (17)	C16—C17	1.47 (2)
N3—C15	1.311 (17)	C16—H16A	0.9702
C1—C6	1.34 (2)	C16—H16B	0.9701
C1—C2	1.42 (2)	O3—C18	1.219 (17)
C2—C7	1.41 (2)	N4—C18	1.363 (17)
C2—C3	1.419 (16)	N4—H4A	0.8601
C3—C10	1.41 (2)	N4—H4B	0.8600
C3—C4	1.44 (2)	N5—C20	1.29 (2)
C4—C5	1.34 (2)	N5—C21	1.324 (18)
C4—C11	1.468 (17)	C18—C19	1.46 (2)
C5—C6	1.440 (16)	C19—C23	1.40 (2)
C5—H5	0.9301	C19—C20	1.404 (17)
C6—H6	0.9302	C20—H20	0.9301
C7—C8	1.37 (2)	C21—C22	1.391 (17)
C7—H7	0.9300	C21—H21	0.9299
C8—C9	1.388 (18)	C22—C23	1.38 (2)
C8—H8	0.9298	C22—H22	0.9300
C9—C10	1.37 (2)	C23—H23	0.9299
C15—S1—C16	97.8 (7)	C13—C12—H12B	117.9
C17—O2—H2	109.5	C11—C12—H12B	117.9
C15—N1—C14	102.5 (10)	H12A—C12—H12B	115.0
C15—N1—C1	130.1 (12)	C11—C13—C12	61.1 (10)
C14—N1—C1	127.3 (11)	C11—C13—H13A	117.7
C14—N2—N3	106.1 (11)	C12—C13—H13A	117.7
C15—N3—N2	106.4 (11)	C11—C13—H13B	117.7
C6—C1—C2	123.0 (11)	C12—C13—H13B	117.7
C6—C1—N1	117.5 (12)	H13A—C13—H13B	114.7
C2—C1—N1	119.5 (12)	N2—C14—N1	112.8 (12)
C7—C2—C3	119.4 (13)	N2—C14—Br1	122.0 (11)
C7—C2—C1	123.4 (11)	N1—C14—Br1	125.0 (9)
C3—C2—C1	117.1 (14)	N3—C15—N1	112.2 (13)
C10—C3—C2	118.2 (13)	N3—C15—S1	124.2 (12)
C10—C3—C4	121.5 (10)	N1—C15—S1	123.6 (10)
C2—C3—C4	120.3 (13)	C17—C16—S1	105.1 (8)
C5—C4—C3	118.8 (11)	C17—C16—H16A	110.7
C5—C4—C11	122.0 (12)	S1—C16—H16A	110.7
C3—C4—C11	119.1 (12)	C17—C16—H16B	110.7
C4—C5—C6	122.0 (14)	S1—C16—H16B	110.7
C4—C5—H5	119.0	H16A—C16—H16B	108.8
C6—C5—H5	119.0	O1—C17—O2	121.0 (13)
C1—C6—C5	118.8 (14)	O1—C17—C16	127.9 (11)
C1—C6—H6	120.6	O2—C17—C16	111.0 (11)
C5—C6—H6	120.6	C18—N4—H4A	120.0
C8—C7—C2	120.7 (11)	C18—N4—H4B	120.0
C8—C7—H7	119.6	H4A—N4—H4B	120.0
C2—C7—H7	119.6	C20—N5—C21	121.7 (12)
C7—C8—C9	120.1 (13)	O3—C18—N4	119.6 (13)
C7—C8—H8	119.9	O3—C18—C19	120.4 (12)
C9—C8—H8	119.9	N4—C18—C19	120.0 (12)
C10—C9—C8	120.8 (13)	C23—C19—C20	118.8 (14)
C10—C9—H9	119.6	C23—C19—C18	120.6 (12)
C8—C9—H9	119.6	C20—C19—C18	120.6 (13)
C9—C10—C3	120.7 (10)	N5—C20—C19	121.3 (14)
C9—C10—H10	119.6	N5—C20—H20	119.3
C3—C10—H10	119.6	C19—C20—H20	119.3
C13—C11—C12	59.8 (10)	N5—C21—C22	120.7 (13)
C13—C11—C4	123.7 (13)	N5—C21—H21	119.6
C12—C11—C4	124.3 (12)	C22—C21—H21	119.6
C13—C11—H11	113.0	C23—C22—C21	119.6 (14)
C12—C11—H11	113.0	C23—C22—H22	120.2
C4—C11—H11	113.0	C21—C22—H22	120.2
C13—C12—C11	59.1 (10)	C22—C23—C19	117.7 (12)
C13—C12—H12A	117.9	C22—C23—H23	121.1
C11—C12—H12A	117.9	C19—C23—H23	121.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.80	2.520 (13)	145
N4—H4A···O1	0.86	2.27	3.091 (14)	160
N4—H4B···N2^i	0.86	2.29	3.132 (16)	165
C12—H12B···O3^ii	0.97	2.58	3.502 (16)	159
C23—H23···N2^i	0.93	2.55	3.473 (17)	174
C23—H23···N3^i	0.93	2.44	3.295 (18)	153

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

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid–urea (1/1) (LESUREFormI)

Crystal data

C17H14BrN3O2S·CH4N2O	V = 980.16 (17) Å^3
Mr = 464.34	Z = 2
Triclinic, P1	F(000) = 472
Hall symbol: -P 1	Dx = 1.573 Mg m^−3
a = 10.8067 (12) Å	Cu Kα radiation, λ = 1.5418 Å
b = 12.1242 (12) Å	T = 298 K
c = 7.5869 (7) Å	Particle morphology: needle
α = 97.387 (17)°	colorless
β = 92.495 (13)°	flat_sheet, 15 × 1 mm
γ = 95.230 (15)°	Specimen preparation: Prepared at 298 K and 101 kPa

Data collection

EMPYREAN (PANanalytical) diffractometer	Data collection mode: reflection
Radiation source: line-focus sealed tube	Scan method: continuous
Curved Germanium (111) monochromator	2θmin = 4.996°, 2θmax = 80.000°, 2θstep = 0.017°
Specimen mounting: thin layer on the non-diffracting silicon plate

Refinement

Refinement on Inet	148 parameters
Least-squares matrix: full with fixed elements per cycle	85 restraints
Rp = 0.024	0 constraints
Rwp = 0.033	H-atom parameters not refined
Rexp = 0.022	Weighting scheme based on measured s.u.'s
RBragg = 0.049	(Δ/σ)max = 0.002
4413 data points	Background function: Chebyshev polynomial up to the 5th order
Excluded region(s): none	Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [010], texture parameter r = 1.05(1).
Profile function: split-type pseudo-Voigt (Toraya, 1986)

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
Br1	0.30960 (18)	−0.02870 (16)	0.2836 (3)	0.0490 (11)*
S1	0.7021 (4)	0.2846 (4)	0.1731 (7)	0.052 (2)*
O1	1.0111 (8)	0.1568 (8)	0.3158 (13)	0.047 (5)*
O2	0.8684 (8)	0.2410 (7)	0.4532 (12)	0.044 (5)*
H2	0.9048	0.2216	0.5395	0.066*
N1	0.4940 (10)	0.1456 (9)	0.2287 (16)	0.055 (6)*
N2	0.5665 (10)	−0.0185 (9)	0.2113 (15)	0.050 (6)*
N3	0.6674 (10)	0.0629 (9)	0.1877 (15)	0.054 (6)*
C1	0.4147 (13)	0.2383 (12)	0.253 (2)	0.062 (8)*
C2	0.4128 (13)	0.3011 (12)	0.423 (2)	0.064 (8)*
C3	0.3422 (12)	0.3945 (11)	0.438 (2)	0.063 (8)*
C4	0.2752 (13)	0.4198 (11)	0.284 (2)	0.058 (8)*
C5	0.2832 (13)	0.3560 (13)	0.124 (2)	0.064 (8)*
H5	0.2385	0.3728	0.0245	0.077*
C6	0.3576 (13)	0.2646 (12)	0.103 (2)	0.057 (8)*
H6	0.3667	0.2247	−0.0082	0.068*
C7	0.4755 (13)	0.2760 (12)	0.577 (2)	0.061 (8)*
H7	0.5232	0.2156	0.5681	0.073*
C8	0.4687 (13)	0.3368 (13)	0.738 (2)	0.064 (8)*
H8	0.5099	0.3173	0.8382	0.077*
C9	0.3995 (13)	0.4291 (12)	0.754 (2)	0.061 (8)*
H9	0.3975	0.4733	0.8634	0.073*
C10	0.3349 (12)	0.4539 (11)	0.608 (2)	0.067 (9)*
H10	0.2842	0.5121	0.6222	0.081*
C11	0.2030 (13)	0.5170 (12)	0.297 (2)	0.059 (8)*
H11	0.2414	0.5824	0.3761	0.071*
C12	0.1262 (13)	0.5434 (12)	0.145 (2)	0.065 (8)*
H12A	0.1223	0.6215	0.1316	0.078*
H12B	0.1237	0.4934	0.0339	0.078*
C13	0.0657 (14)	0.5015 (12)	0.295 (2)	0.068 (8)*
H13A	0.0259	0.4256	0.2768	0.082*
H13B	0.0245	0.5537	0.3745	0.082*
C14	0.4687 (14)	0.0355 (12)	0.238 (2)	0.056 (8)*
C15	0.6188 (13)	0.1569 (13)	0.196 (2)	0.063 (8)*
C16	0.8559 (14)	0.2417 (12)	0.156 (2)	0.064 (8)*
H16A	0.8521	0.1799	0.0606	0.077*
H16B	0.9080	0.3030	0.1188	0.077*
C17	0.9212 (13)	0.2070 (12)	0.312 (2)	0.057 (8)*
O3	0.9751 (8)	0.1785 (8)	0.7321 (13)	0.055 (5)*
N4	1.1348 (10)	0.0911 (8)	0.6355 (16)	0.054 (7)*
H4A	1.1171	0.1036	0.5287	0.065*
H4B	1.1976	0.0553	0.6573	0.065*
N5	1.0938 (10)	0.1120 (9)	0.9363 (16)	0.053 (6)*
H5A	1.0506	0.1376	1.0221	0.064*
H5B	1.1566	0.0760	0.9577	0.064*
C18	1.0634 (13)	0.1280 (12)	0.770 (2)	0.059 (8)*

Geometric parameters (Å, º)

Br1—C14	1.886 (15)	C7—H7	0.9303
S1—C15	1.751 (16)	C8—C9	1.40 (2)
S1—C16	1.791 (16)	C8—H8	0.9303
O1—C17	1.193 (18)	C9—C10	1.36 (2)
O2—C17	1.274 (17)	C9—H9	0.9301
O2—H2	0.8200	C10—H10	0.9298
N1—C14	1.350 (19)	C11—C12	1.48 (2)
N1—C15	1.380 (18)	C11—C13	1.48 (2)
N1—C1	1.472 (19)	C11—H11	0.9801
N2—C14	1.303 (19)	C12—C13	1.46 (2)
N2—N3	1.436 (15)	C12—H12A	0.9703
N3—C15	1.29 (2)	C12—H12B	0.9701
C1—C6	1.36 (2)	C13—H13A	0.9698
C1—C2	1.41 (2)	C13—H13B	0.9704
C2—C7	1.41 (2)	C16—C17	1.48 (2)
C2—C3	1.42 (2)	C16—H16A	0.9699
C3—C10	1.41 (2)	C16—H16B	0.9699
C3—C4	1.43 (2)	O3—C18	1.223 (18)
C4—C5	1.36 (2)	N4—C18	1.360 (18)
C4—C11	1.47 (2)	N4—H4A	0.8599
C5—C6	1.42 (2)	N4—H4B	0.8603
C5—H5	0.9301	N5—C18	1.33 (2)
C6—H6	0.9301	N5—H5A	0.8601
C7—C8	1.35 (2)	N5—H5B	0.8599
C15—S1—C16	100.1 (7)	C4—C11—H11	114.6
C17—O2—H2	109.5	C12—C11—H11	114.6
C14—N1—C15	104.1 (12)	C13—C11—H11	114.6
C14—N1—C1	131.0 (12)	C13—C12—C11	60.4 (11)
C15—N1—C1	124.9 (12)	C13—C12—H12A	117.7
C14—N2—N3	106.8 (11)	C11—C12—H12A	117.8
C15—N3—N2	105.2 (11)	C13—C12—H12B	117.7
C6—C1—C2	124.1 (14)	C11—C12—H12B	117.7
C6—C1—N1	116.2 (13)	H12A—C12—H12B	114.8
C2—C1—N1	119.3 (13)	C12—C13—C11	60.3 (11)
C7—C2—C1	124.1 (14)	C12—C13—H13A	117.8
C7—C2—C3	118.3 (13)	C11—C13—H13A	117.8
C1—C2—C3	117.6 (14)	C12—C13—H13B	117.7
C10—C3—C2	117.8 (14)	C11—C13—H13B	117.8
C10—C3—C4	122.9 (13)	H13A—C13—H13B	114.8
C2—C3—C4	119.2 (13)	N2—C14—N1	111.6 (13)
C5—C4—C3	119.7 (13)	N2—C14—Br1	125.5 (11)
C5—C4—C11	120.4 (14)	N1—C14—Br1	122.9 (11)
C3—C4—C11	119.9 (13)	N3—C15—N1	112.2 (13)
C4—C5—C6	122.3 (15)	N3—C15—S1	124.1 (11)
C4—C5—H5	118.8	N1—C15—S1	123.7 (12)
C6—C5—H5	118.9	C17—C16—S1	120.1 (11)
C1—C6—C5	116.9 (14)	C17—C16—H16A	107.3
C1—C6—H6	121.5	S1—C16—H16A	107.3
C5—C6—H6	121.6	C17—C16—H16B	107.3
C8—C7—C2	122.2 (14)	S1—C16—H16B	107.3
C8—C7—H7	118.9	H16A—C16—H16B	106.9
C2—C7—H7	118.9	O1—C17—O2	122.0 (14)
C7—C8—C9	119.7 (14)	O1—C17—C16	128.3 (14)
C7—C8—H8	120.2	O2—C17—C16	109.7 (13)
C9—C8—H8	120.1	C18—N4—H4A	120.0
C10—C9—C8	119.6 (13)	C18—N4—H4B	120.0
C10—C9—H9	120.2	H4A—N4—H4B	120.0
C8—C9—H9	120.2	C18—N5—H5A	120.0
C9—C10—C3	122.2 (13)	C18—N5—H5B	120.0
C9—C10—H10	118.9	H5A—N5—H5B	120.0
C3—C10—H10	118.9	O3—C18—N5	122.7 (13)
C4—C11—C12	122.3 (13)	O3—C18—N4	117.5 (13)
C4—C11—C13	120.2 (12)	N5—C18—N4	119.8 (13)
C12—C11—C13	59.3 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.78	2.596 (13)	177
N4—H4A···O1	0.86	2.14	2.952 (15)	157
N4—H4B···N3^i	0.86	2.50	3.313 (15)	159
N5—H5A···O1^ii	0.86	2.27	3.049 (15)	150

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

2-{[5-Bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-\ 3-yl]sulfanyl}acetic acid–urea (1/1) (LESUREFormII)

Crystal data

C17H14BrN3O2S·CH4N2O	F(000) = 1887.4843
Mr = 464.35	Dx = 1.571 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.9993 (5) Å	Cell parameters from 4931 reflections
b = 15.2290 (5) Å	θ = 3.7–23.5°
c = 24.0797 (10) Å	µ = 2.23 mm^−1
β = 103.193 (4)°	T = 150 K
V = 3927.1 (3) Å^3	Needle, colourless
Z = 8	0.30 × 0.12 × 0.10 mm

Data collection

Xcalibur, Eos, Nova diffractometer	8975 independent reflections
Radiation source: micro-focus sealed X-ray tube, Mova (Mo) X-ray Source	5645 reflections with I ≥ 2u(I)
Mirror monochromator	Rint = 0.093
Detector resolution: 8.0419 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −14→14
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −19→19
Tmin = 0.715, Tmax = 1.000	l = −31→30
33889 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	62 constraints
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0312P)^2 + 2.5686P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
8975 reflections	Δρmax = 2.18 e Å^−3
509 parameters	Δρmin = −1.29 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	−0.1045 (5)	0.1033 (3)	0.5001 (2)	0.0274 (12)
C2	0.0310 (5)	0.1885 (3)	0.5537 (2)	0.0276 (12)
C3	0.2048 (5)	0.2431 (3)	0.6468 (2)	0.0338 (13)
H3a	0.1318 (5)	0.2404 (3)	0.6630 (2)	0.0405 (15)*
H3b	0.2562 (5)	0.2917 (3)	0.6646 (2)	0.0405 (15)*
C4	0.2779 (5)	0.1585 (3)	0.6599 (2)	0.0283 (12)
C5	0.0297 (4)	0.1942 (3)	0.44944 (19)	0.0227 (11)
C6	0.0898 (5)	0.1378 (3)	0.4208 (2)	0.0298 (12)
H6	0.1029 (5)	0.0799 (3)	0.4329 (2)	0.0358 (15)*
C7	0.1320 (5)	0.1668 (3)	0.3734 (2)	0.0307 (12)
H7	0.1694 (5)	0.1270 (3)	0.3532 (2)	0.0369 (14)*
C8	0.1194 (5)	0.2529 (3)	0.3561 (2)	0.0278 (12)
C9	0.0563 (4)	0.3129 (3)	0.3853 (2)	0.0239 (11)
C10	0.0077 (4)	0.2831 (3)	0.43232 (18)	0.0202 (10)
C11	−0.0574 (4)	0.3429 (3)	0.4598 (2)	0.0239 (11)
H11	−0.0917 (4)	0.3235 (3)	0.4896 (2)	0.0287 (13)*
C12	−0.0706 (5)	0.4292 (3)	0.4432 (2)	0.0293 (12)
H12	−0.1134 (5)	0.4679 (3)	0.4618 (2)	0.0352 (14)*
C13	−0.0202 (5)	0.4593 (3)	0.3985 (2)	0.0307 (12)
H13	−0.0278 (5)	0.5182 (3)	0.3880 (2)	0.0369 (15)*
C14	0.0405 (5)	0.4024 (3)	0.3699 (2)	0.0307 (12)
H14	0.0720 (5)	0.4232 (3)	0.3397 (2)	0.0368 (15)*
C15	0.1741 (5)	0.2854 (3)	0.3085 (2)	0.0360 (13)
H15	0.1148 (5)	0.3100 (3)	0.2755 (2)	0.0432 (16)*
C16	0.2860 (5)	0.2410 (3)	0.2962 (2)	0.0401 (14)
H16a	0.3195 (5)	0.1906 (3)	0.3193 (2)	0.0482 (17)*
H16b	0.2926 (5)	0.2378 (3)	0.2567 (2)	0.0482 (17)*
C17	0.2991 (6)	0.3289 (4)	0.3241 (3)	0.0544 (17)
H17a	0.3135 (6)	0.3791 (4)	0.3016 (3)	0.065 (2)*
H17b	0.3404 (6)	0.3319 (4)	0.3642 (3)	0.065 (2)*
C21	0.4302 (5)	0.3990 (3)	0.54182 (19)	0.0236 (11)
C22	0.6134 (5)	0.3569 (3)	0.58664 (19)	0.0251 (11)
C23	0.8035 (5)	0.2990 (3)	0.67225 (19)	0.0280 (12)
H23a	0.8531 (5)	0.2465 (3)	0.68289 (19)	0.0336 (14)*
H23b	0.7290 (5)	0.2939 (3)	0.68713 (19)	0.0336 (14)*
C24	0.8779 (5)	0.3785 (3)	0.69850 (19)	0.0243 (11)
C25	0.5555 (4)	0.3168 (3)	0.48275 (18)	0.0197 (10)
C26	0.6144 (5)	0.3585 (3)	0.4467 (2)	0.0273 (11)
H26	0.6428 (5)	0.4158 (3)	0.4542 (2)	0.0327 (14)*
C27	0.6321 (5)	0.3144 (3)	0.39807 (19)	0.0260 (11)
H27	0.6736 (5)	0.3433 (3)	0.37381 (19)	0.0312 (13)*
C28	0.5907 (4)	0.2303 (3)	0.38480 (18)	0.0203 (10)
C29	0.5256 (4)	0.1865 (3)	0.42229 (18)	0.0195 (10)
C30	0.5081 (4)	0.2298 (3)	0.47223 (18)	0.0184 (10)
C31	0.4453 (5)	0.1869 (3)	0.50923 (19)	0.0275 (11)
H31	0.4361 (5)	0.2151 (3)	0.54229 (19)	0.0330 (14)*
C32	0.3978 (5)	0.1047 (3)	0.4973 (2)	0.0375 (14)
H32	0.3559 (5)	0.0771 (3)	0.5219 (2)	0.0450 (16)*
C33	0.4125 (5)	0.0619 (3)	0.4476 (2)	0.0349 (13)
H33	0.3787 (5)	0.0062 (3)	0.4393 (2)	0.0419 (16)*
C34	0.4752 (5)	0.1005 (3)	0.41153 (19)	0.0273 (12)
H34	0.4853 (5)	0.0703 (3)	0.37934 (19)	0.0328 (14)*
C35	0.6106 (5)	0.1871 (3)	0.33281 (19)	0.0294 (12)
H35	0.5807 (5)	0.1264 (3)	0.32770 (19)	0.0352 (14)*
C36	0.7263 (5)	0.2052 (4)	0.3112 (2)	0.0389 (14)
H36a	0.7846 (5)	0.2486 (4)	0.3314 (2)	0.0467 (16)*
H36b	0.7644 (5)	0.1564 (4)	0.2957 (2)	0.0467 (16)*
C37	0.6026 (5)	0.2368 (3)	0.2784 (2)	0.0358 (13)
H37a	0.5658 (5)	0.2072 (3)	0.2429 (2)	0.0430 (16)*
H37b	0.5860 (5)	0.2993 (3)	0.2786 (2)	0.0430 (16)*
C40	0.5287 (4)	0.4946 (3)	0.25027 (19)	0.0199 (10)
N1	−0.1192 (4)	0.0935 (3)	0.55236 (18)	0.0340 (11)
N2	−0.0296 (4)	0.1491 (3)	0.58705 (17)	0.0337 (11)
N3	−0.0131 (4)	0.1637 (2)	0.49808 (16)	0.0247 (9)
N4	0.5597 (4)	0.3923 (2)	0.62437 (17)	0.0282 (10)
N5	0.4392 (4)	0.4191 (2)	0.59548 (17)	0.0274 (9)
N6	0.5367 (4)	0.3603 (2)	0.53353 (15)	0.0225 (9)
N11	0.6314 (4)	0.5156 (3)	0.29063 (17)	0.0323 (10)
H11a	0.6826 (14)	0.545 (2)	0.2755 (3)	0.0388 (12)*
H11b	0.6089 (5)	0.548 (2)	0.3160 (8)	0.0388 (12)*
N12	0.4175 (4)	0.5096 (2)	0.26117 (16)	0.0252 (9)
H12a	0.4122 (4)	0.5322 (2)	0.29330 (16)	0.0303 (11)*
H12b	0.3507 (4)	0.4968 (2)	0.23611 (16)	0.0303 (11)*
O1	0.2329 (3)	0.0913 (2)	0.67171 (16)	0.0400 (10)
O2	0.3967 (3)	0.1674 (2)	0.65853 (16)	0.0375 (9)
H2	0.4322 (13)	0.1199 (8)	0.665 (2)	0.0562 (14)*
O3	0.9978 (3)	0.3701 (2)	0.70006 (15)	0.0315 (8)
H3	1.0365 (6)	0.410 (2)	0.7189 (19)	0.0473 (13)*
O4	0.8308 (3)	0.4412 (2)	0.71645 (14)	0.0302 (8)
O5	0.5392 (3)	0.46065 (19)	0.20385 (12)	0.0231 (7)
S2	0.75922 (12)	0.30727 (9)	0.59523 (5)	0.0317 (3)
Br2	0.29317 (5)	0.41848 (3)	0.48198 (2)	0.02899 (14)
Br1	−0.18605 (5)	0.04226 (3)	0.43618 (2)	0.03785 (16)
C41	0.1220 (5)	−0.0328 (3)	0.29262 (19)	0.0217 (10)
N13	0.2225 (4)	−0.0661 (2)	0.32990 (17)	0.0298 (10)
H13a	0.2016 (10)	−0.079 (2)	0.3614 (5)	0.0358 (12)*
H13b	0.246 (2)	−0.1132 (13)	0.3157 (6)	0.0358 (12)*
N14	0.0095 (4)	−0.0435 (3)	0.30283 (17)	0.0320 (10)
H14a	0.0011 (4)	−0.0712 (3)	0.33285 (17)	0.0384 (12)*
H14b	−0.0550 (4)	−0.0226 (3)	0.27944 (17)	0.0384 (12)*
O6	0.1381 (3)	0.0078 (2)	0.24932 (13)	0.0260 (8)
S1	0.15579 (13)	0.26295 (8)	0.57135 (5)	0.0351 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.022 (3)	0.027 (3)	0.033 (3)	0.003 (2)	0.007 (2)	0.017 (2)
C2	0.030 (3)	0.028 (3)	0.024 (3)	0.009 (2)	0.005 (2)	0.013 (2)
C3	0.033 (3)	0.041 (3)	0.028 (3)	0.003 (2)	0.006 (3)	0.001 (2)
C4	0.021 (3)	0.041 (3)	0.021 (3)	0.005 (2)	0.000 (2)	0.006 (2)
C5	0.021 (3)	0.023 (2)	0.025 (3)	−0.008 (2)	0.005 (2)	0.004 (2)
C6	0.038 (3)	0.014 (2)	0.042 (3)	0.000 (2)	0.018 (3)	0.005 (2)
C7	0.035 (3)	0.026 (3)	0.038 (3)	0.001 (2)	0.022 (3)	0.002 (2)
C8	0.036 (3)	0.027 (3)	0.024 (3)	−0.004 (2)	0.013 (2)	0.000 (2)
C9	0.023 (3)	0.023 (2)	0.027 (3)	−0.005 (2)	0.009 (2)	0.005 (2)
C10	0.016 (2)	0.022 (2)	0.021 (2)	0.0008 (18)	0.000 (2)	0.0051 (19)
C11	0.018 (3)	0.028 (3)	0.026 (3)	−0.004 (2)	0.005 (2)	0.007 (2)
C12	0.027 (3)	0.032 (3)	0.029 (3)	0.002 (2)	0.007 (2)	−0.002 (2)
C13	0.032 (3)	0.020 (2)	0.039 (3)	0.002 (2)	0.007 (3)	0.010 (2)
C14	0.035 (3)	0.027 (3)	0.032 (3)	−0.001 (2)	0.013 (3)	0.007 (2)
C15	0.039 (3)	0.042 (3)	0.032 (3)	0.008 (3)	0.018 (3)	0.009 (2)
C16	0.044 (4)	0.052 (4)	0.030 (3)	0.009 (3)	0.022 (3)	0.010 (3)
C17	0.063 (5)	0.043 (4)	0.064 (4)	−0.002 (3)	0.031 (4)	0.011 (3)
C21	0.025 (3)	0.027 (3)	0.021 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
C22	0.030 (3)	0.028 (3)	0.019 (2)	−0.002 (2)	0.008 (2)	−0.004 (2)
C23	0.028 (3)	0.028 (3)	0.029 (3)	−0.002 (2)	0.008 (2)	0.001 (2)
C24	0.026 (3)	0.031 (3)	0.015 (2)	0.002 (2)	0.003 (2)	0.005 (2)
C25	0.018 (2)	0.022 (2)	0.019 (2)	−0.0013 (19)	0.004 (2)	−0.0052 (19)
C26	0.030 (3)	0.020 (2)	0.033 (3)	−0.005 (2)	0.011 (3)	−0.007 (2)
C27	0.032 (3)	0.031 (3)	0.019 (2)	−0.008 (2)	0.012 (2)	0.000 (2)
C28	0.018 (3)	0.026 (2)	0.017 (2)	−0.0003 (19)	0.004 (2)	−0.0036 (19)
C29	0.020 (3)	0.021 (2)	0.017 (2)	0.0013 (19)	0.003 (2)	−0.0042 (18)
C30	0.017 (2)	0.018 (2)	0.019 (2)	0.0002 (18)	0.002 (2)	−0.0036 (18)
C31	0.033 (3)	0.030 (3)	0.021 (3)	−0.002 (2)	0.010 (2)	−0.002 (2)
C32	0.045 (4)	0.032 (3)	0.038 (3)	−0.011 (3)	0.016 (3)	0.006 (2)
C33	0.043 (4)	0.018 (3)	0.043 (3)	−0.006 (2)	0.008 (3)	−0.004 (2)
C34	0.038 (3)	0.024 (3)	0.022 (3)	−0.002 (2)	0.011 (2)	−0.003 (2)
C35	0.037 (3)	0.035 (3)	0.018 (2)	0.000 (2)	0.009 (2)	−0.010 (2)
C36	0.038 (3)	0.056 (4)	0.026 (3)	−0.001 (3)	0.015 (3)	−0.016 (3)
C37	0.048 (4)	0.040 (3)	0.019 (3)	0.004 (3)	0.007 (3)	−0.005 (2)
C40	0.024 (3)	0.018 (2)	0.020 (2)	−0.0006 (19)	0.010 (2)	0.0015 (19)
N1	0.027 (3)	0.039 (3)	0.040 (3)	0.009 (2)	0.016 (2)	0.023 (2)
N2	0.036 (3)	0.036 (2)	0.032 (2)	0.009 (2)	0.015 (2)	0.008 (2)
N3	0.026 (2)	0.025 (2)	0.024 (2)	0.0021 (17)	0.006 (2)	0.0090 (17)
N4	0.024 (2)	0.034 (2)	0.027 (2)	0.0009 (18)	0.007 (2)	−0.0079 (18)
N5	0.027 (2)	0.028 (2)	0.028 (2)	0.0012 (18)	0.009 (2)	−0.0054 (18)
N6	0.025 (2)	0.023 (2)	0.019 (2)	0.0012 (17)	0.0044 (19)	−0.0044 (16)
N11	0.025 (3)	0.046 (3)	0.028 (2)	−0.007 (2)	0.010 (2)	−0.011 (2)
N12	0.024 (2)	0.031 (2)	0.023 (2)	−0.0013 (18)	0.010 (2)	−0.0038 (17)
O1	0.023 (2)	0.038 (2)	0.059 (3)	−0.0024 (16)	0.010 (2)	0.0193 (18)
O2	0.028 (2)	0.035 (2)	0.049 (2)	0.0020 (16)	0.009 (2)	0.0096 (18)
O3	0.024 (2)	0.034 (2)	0.035 (2)	−0.0020 (15)	0.0061 (18)	−0.0117 (16)
O4	0.0211 (19)	0.0300 (19)	0.042 (2)	0.0006 (14)	0.0133 (17)	−0.0096 (16)
O5	0.0235 (19)	0.0261 (17)	0.0216 (17)	−0.0045 (14)	0.0092 (16)	−0.0061 (14)
S2	0.0255 (7)	0.0453 (8)	0.0239 (7)	0.0053 (6)	0.0048 (6)	−0.0096 (6)
Br2	0.0251 (3)	0.0304 (3)	0.0302 (3)	0.0016 (2)	0.0036 (2)	−0.0084 (2)
Br1	0.0327 (3)	0.0335 (3)	0.0433 (3)	−0.0112 (2)	0.0003 (3)	0.0119 (2)
C41	0.023 (3)	0.021 (2)	0.021 (2)	−0.007 (2)	0.003 (2)	0.0021 (19)
N13	0.035 (3)	0.030 (2)	0.025 (2)	0.0035 (19)	0.008 (2)	0.0053 (18)
N14	0.022 (2)	0.049 (3)	0.025 (2)	−0.003 (2)	0.005 (2)	0.0139 (19)
O6	0.0199 (19)	0.0347 (18)	0.0262 (18)	0.0009 (14)	0.0113 (16)	0.0075 (15)
S1	0.0376 (9)	0.0371 (7)	0.0278 (7)	−0.0048 (6)	0.0016 (7)	0.0075 (6)

Geometric parameters (Å, º)

C1—N1	1.314 (6)	C22—N6	1.363 (5)
C1—N3	1.371 (6)	C22—S2	1.742 (5)
C1—Br1	1.845 (5)	C23—C24	1.516 (6)
C2—N2	1.302 (6)	C23—S2	1.811 (5)
C2—N3	1.369 (6)	C24—O3	1.317 (6)
C2—S1	1.756 (5)	C24—O4	1.211 (5)
C3—C4	1.514 (6)	C25—C26	1.354 (6)
C3—S1	1.798 (5)	C25—C30	1.426 (6)
C4—O1	1.199 (6)	C25—N6	1.446 (5)
C4—O2	1.322 (6)	C26—C27	1.402 (6)
C5—C6	1.363 (6)	C27—C28	1.373 (6)
C5—C10	1.420 (6)	C28—C29	1.437 (6)
C5—N3	1.436 (6)	C28—C35	1.474 (6)
C6—C7	1.398 (6)	C29—C30	1.422 (6)
C7—C8	1.372 (6)	C29—C34	1.422 (6)
C8—C9	1.426 (6)	C30—C31	1.406 (6)
C8—C15	1.497 (7)	C31—C32	1.362 (6)
C9—C10	1.431 (6)	C32—C33	1.402 (7)
C9—C14	1.414 (6)	C33—C34	1.361 (7)
C10—C11	1.413 (6)	C35—C36	1.505 (7)
C11—C12	1.372 (6)	C35—C37	1.498 (6)
C12—C13	1.397 (7)	C36—C37	1.488 (7)
C13—C14	1.370 (7)	C40—N11	1.349 (6)
C15—C16	1.493 (7)	C40—N12	1.329 (6)
C15—C17	1.495 (8)	C40—O5	1.261 (5)
C16—C17	1.491 (7)	N1—N2	1.418 (6)
C21—N5	1.310 (5)	N4—N5	1.409 (5)
C21—N6	1.366 (6)	C41—N13	1.353 (6)
C21—Br2	1.856 (5)	C41—N14	1.325 (6)
C22—N4	1.308 (6)	C41—O6	1.259 (5)
N3—C1—N1	111.1 (4)	O4—C24—O3	125.0 (4)
Br1—C1—N1	126.8 (4)	C30—C25—C26	122.1 (4)
Br1—C1—N3	122.0 (4)	N6—C25—C26	120.6 (4)
N3—C2—N2	111.0 (4)	N6—C25—C30	117.3 (4)
S1—C2—N2	129.1 (4)	C27—C26—C25	119.3 (4)
S1—C2—N3	119.9 (4)	C28—C27—C26	122.7 (4)
S1—C3—C4	112.1 (3)	C29—C28—C27	118.2 (4)
O1—C4—C3	123.2 (5)	C35—C28—C27	120.5 (4)
O2—C4—C3	112.9 (4)	C35—C28—C29	121.2 (4)
O2—C4—O1	123.9 (5)	C30—C29—C28	119.9 (4)
C10—C5—C6	121.6 (4)	C34—C29—C28	122.8 (4)
N3—C5—C6	119.7 (4)	C34—C29—C30	117.3 (4)
N3—C5—C10	118.7 (4)	C29—C30—C25	117.8 (4)
C7—C6—C5	120.2 (4)	C31—C30—C25	122.1 (4)
C8—C7—C6	121.4 (5)	C31—C30—C29	120.1 (4)
C9—C8—C7	119.2 (4)	C32—C31—C30	120.8 (4)
C15—C8—C7	121.3 (4)	C33—C32—C31	119.6 (5)
C15—C8—C9	119.5 (4)	C34—C33—C32	121.2 (4)
C10—C9—C8	120.0 (4)	C33—C34—C29	121.0 (4)
C14—C9—C8	122.2 (4)	C36—C35—C28	120.8 (4)
C14—C9—C10	117.9 (4)	C37—C35—C28	121.8 (4)
C9—C10—C5	117.5 (4)	C37—C35—C36	59.4 (3)
C11—C10—C5	123.3 (4)	C37—C36—C35	60.0 (3)
C11—C10—C9	119.2 (4)	C36—C37—C35	60.5 (3)
C12—C11—C10	120.7 (4)	N12—C40—N11	118.3 (4)
C13—C12—C11	120.4 (5)	O5—C40—N11	120.3 (4)
C14—C13—C12	120.3 (4)	O5—C40—N12	121.4 (4)
C13—C14—C9	121.5 (5)	N2—N1—C1	106.0 (4)
C16—C15—C8	119.8 (4)	N1—N2—C2	107.3 (4)
C17—C15—C8	117.5 (5)	C2—N3—C1	104.5 (4)
C17—C15—C16	59.9 (4)	C5—N3—C1	128.7 (4)
C17—C16—C15	60.1 (4)	C5—N3—C2	126.8 (4)
C16—C17—C15	60.0 (4)	N5—N4—C22	107.4 (4)
N6—C21—N5	111.8 (4)	N4—N5—C21	105.7 (4)
Br2—C21—N5	126.4 (4)	C22—N6—C21	104.3 (4)
Br2—C21—N6	121.8 (3)	C25—N6—C21	127.8 (4)
N6—C22—N4	110.8 (4)	C25—N6—C22	126.7 (4)
S2—C22—N4	130.3 (4)	C23—S2—C22	100.2 (2)
S2—C22—N6	119.0 (3)	N14—C41—N13	119.2 (4)
S2—C23—C24	111.4 (3)	O6—C41—N13	119.0 (4)
O3—C24—C23	112.1 (4)	O6—C41—N14	121.8 (4)
O4—C24—C23	122.9 (5)	C3—S1—C2	100.0 (2)