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2-Methyl-4-(4-methyl­piperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine, C17H20N4S, commonly known as olanzapine, is a psychotropic agent that belongs to the thienobenzodi­azepine class of drugs. A new polymorph form IV was obtained upon attempted cocrystallization with nicotinamide in a 1:1 ratio from an ethyl acetate solution. Two butterfly-like mol­ecules form centrosymmetric dimers stabilized by weak C—H...π inter­actions between the 4-methyl­piperazin-1-yl fragment and the benzene/thio­phene aromatic system. Form IV consists of a herringbone arrangement of dimers, whereas the previously reported form II has parallel dimers. Both crystal structures are sustained by an N—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111043952/eg3078sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111043952/eg3078Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111043952/eg3078Isup3.cml
Supplementary material

CCDC reference: 855975

Comment top

Olanzapine [systematic name: 2-methyl-4-(4-methylpiperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine], (I), is a frontline psychotropic drug marketed by Eli Lilly under the brand name Zyprexa. It is one of the top 20 prescription drugs based on a recent survey (Craig & Stitzel, 1997; Lindsley, 2010). It is a yellow crystalline solid that is practically insoluble in water (43 mg l-1), sparingly soluble in acetonitrile and ethyl acetate, and freely soluble in chloroform. According to the Biopharmaceutics Classification System (BCS), olanzapine belongs to the Class II category, namely a drug with low solubility and high permeability. Six solid-state forms of olanzapine have been characterized (Bunnell et al., 1996, 1998; Hamied et al., 2002; Sundaram et al., 2006; Reguri & Chakka, 2005; Wawrzycka-Gorczyca et al., 2004), together with a few solvates and hydrates (Reutzel-Edens et al., 2003; Almarsson et al., 2007; Hickey & Remenar, 2006; Wawrzycka-Gorczyca et al., 2004, 2007; Capuano et al., 2003; Larsen, 1997; Bunnell et al., 1997; Kotar-Zordan et al., 2005; Dalmases Barjoan et al., 2006, 2007) and salts with carboxylic acids (Keltjens, 2005; Simonic et al., 2006; Kozluk, 2007; Bush, 2008; Mesar et al., 2008; Ravikumar et al., 2005; Sridhar & Ravikumar, 2007; Thakuria & Nangia, 2011). Only one X-ray crystal structure of olanzapine has been reported to date (Reutzel-Edens et al., 2003; Wawrzycka-Gorczyca et al., 2004), the powder X-ray diffraction pattern (PXRD) of which matched that of a polymorph designated form II in US patents (Bunnell et al., 1996, 1998). We now report the X-ray crystal structure of a polymorph of olanzapine, designated form IV (Hamied et al., 2002) by PXRD overlay.

The molecule of (I) has a central seven-membered diazepine ring which is fused with a benzene, a thiophene and an N-methylpiperazine ring (Fig. 1). The boat conformation of the central 1,5-diazepine ring defines the overall butterfly shape of the molecule, but the N-methylpiperazine ring can have conformational variation (Reutzel-Edens et al., 2003).

Cocrystallization of olanzapine with nicotinamide in 1:1 ratio from ethyl acetate afforded block-shaped pale-yellow crystals of olanzapine form IV in the space group P21/c. The expected cocrystal with nicotinamide was not obtained. Such observations are not unusual (Day et al., 2006; Li et al., 2011; Sanphui et al., 2011; Vishweshwar et al., 2005). The asymmetric unit of olanzapine form IV contains one molecule of olanzapine, having a single hydrogen-bond donor, N2—H2, and two exposed acceptors, imine atom N1 and piperazine atom N4, which are hydrogen-bonded in the crystal structure.

Two butterfly-like molecules form centrosymmetric dimers (Reutzel-Edens et al., 2003; Wawrzycka-Gorczyca et al., 2004) in the crystal structures of both forms IV and II, which are stabilized by weak C—H···π interactions between the 4-methylpiperazin-1-yl fragment (C15—H15 in form IV) and the benzene/thiophene aromatic system. Theoretical calculations estimated that this C—H···π binding energy is about 8 kcal mol-1 (1 kcal mol-1 = 4.184 kJ mol-1) (Wawrzycka-Gorczyca et al., 2007). The packing of such dimer motifs in the two structures is completely different: form IV consists of a herringbone arrangement of dimers, whereas they are parallel in form II (Fig. 2).

The intermolecular interaction N2—H2···N1i [symmetry code: (i) x, -y+1/2, z+1/2] (Table 1) links the molecules in form IV into extended chains which can be described by the graph-set notation C(5) (Bernstein et al., 1995), and thereby connects the inversion-related dimers to form columns along the c axis. A similar, slightly shorter, interaction [H···N = 2.27 (2) Å] leading to similar chains occurs in the form II structure. The chains in form IV are further enhanced by a very weak intermolecular C—H···N interaction between piperazine atom N4 and a methyl H atom, H8B, on the thiophene ring of the molecule two links further on in the chain. This C—H···N interaction can be described with a graph-set notation of C(10).

Related literature top

For related literature, see: Almarsson et al. (2007); Bernstein et al. (1995); Bunnell et al. (1996, 1997, 1998); Bush (2008); Capuano et al. (2003); Craig & Stitzel (1997); Dalmases & Bessa Bellmunt (2006); Dalmases & Herbera Espinal (2007); Day et al. (2006); Hamied et al. (2002); Hickey & Remenar (2006); Keltjens (2005); Kotar-Zordan, Lenarsic, Grcman, Smrkolj, Meden, Simonic, Zupet, Gnidovec & Benkic (2005); Kozluk (2007); Larsen (1997); Li et al. (2011); Lindsley (2010); Mesar et al. (2008); Ravikumar et al. (2005); Reguri & Chakka (2005); Reutzel-Edens, Bush, Magee, Stephenson & Byrn (2003); Sanphui et al. (2011); Simonic et al. (2006); Sridhar & Ravikumar (2007); Sundaram et al. (2006); Thakuria & Nangia (2011); Vishweshwar et al. (2005); Wawrzycka-Gorczyca, Borowski, Osypiuk-Tomasik, Mazur & Koziol (2007); Wawrzycka-Gorczyca, Koziol, Glice & Cybulski (2004).

Experimental top

A solution of olanzapine (60 mg, 0.2 mmol) and nicotinamide (24 mg, 0.2 mmol) in 1:1 ratio in ethyl acetate (approximately 10 ml) was allowed to evaporate slowly at room temperature for 5–10 d. Complete evaporation of the solvent resulted in a mixture of crytalline nicotinamide and olanzapine. Colourless transparent crystals of nicotinamide were manually separated. Olanzapine form IV, as yellow block-shaped crystals, was selected for X-ray diffraction. Because the polymorph was obtained from a cocrystallization experiment, the phase purity of the bulk sample could not be confirmed by powder diffraction.

Refinement top

The N-bonded atom H2 was located from a difference-electron density map, and its positional and isotropic displacement parameters were refined freely. H atoms attached to C atoms were positioned geometrically and treated as riding on their C atoms, with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene, and C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of olanzapine form IV, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. (a) The parallel stacking of olanzapine dimers in olanzapine form II. (b) The herringbone arrangement of dimers in form IV.
2-Methyl-4-(4-methylpiperazin-1-yl)-10H- thieno[2,3-b][1,5]benzodiazepin top
Crystal data top
C17H20N4SF(000) = 664
Mr = 312.44Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5126 reflections
a = 9.9130 (8) Åθ = 2.4–26.0°
b = 16.5329 (13) ŵ = 0.20 mm1
c = 9.9992 (8) ÅT = 298 K
β = 98.023 (1)°Block, yellow
V = 1622.7 (2) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
CCD area detector
diffractometer
3202 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1212
Tmin = 0.942, Tmax = 0.961k = 2020
16674 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.6929P]
where P = (Fo2 + 2Fc2)/3
3202 reflections(Δ/σ)max = 0.005
205 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C17H20N4SV = 1622.7 (2) Å3
Mr = 312.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.9130 (8) ŵ = 0.20 mm1
b = 16.5329 (13) ÅT = 298 K
c = 9.9992 (8) Å0.30 × 0.30 × 0.20 mm
β = 98.023 (1)°
Data collection top
CCD area detector
diffractometer
3202 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2963 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.961Rint = 0.026
16674 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.29 e Å3
3202 reflectionsΔρmin = 0.23 e Å3
205 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
S10.40573 (5)0.19412 (3)0.25828 (5)0.0407 (2)
N10.60588 (15)0.13996 (9)0.13305 (14)0.0354 (5)
N20.58482 (16)0.25183 (10)0.09664 (17)0.0393 (5)
N30.39428 (15)0.08739 (10)0.20153 (15)0.0373 (5)
N40.21058 (16)0.00388 (10)0.38737 (15)0.0402 (5)
C10.71583 (18)0.16340 (11)0.03516 (18)0.0351 (5)
C20.71107 (18)0.21911 (11)0.06962 (18)0.0360 (5)
C30.48458 (18)0.19517 (10)0.11415 (17)0.0340 (5)
C40.44100 (17)0.13255 (11)0.03005 (17)0.0328 (5)
C50.48642 (17)0.12223 (10)0.10305 (17)0.0318 (5)
C60.34527 (18)0.08211 (11)0.08539 (18)0.0363 (5)
C70.31347 (18)0.10787 (12)0.20525 (18)0.0381 (5)
C80.2159 (2)0.07292 (15)0.2909 (2)0.0527 (7)
C90.8306 (2)0.24460 (13)0.1468 (2)0.0477 (7)
C100.9558 (2)0.21593 (16)0.1236 (2)0.0571 (8)
C110.9623 (2)0.15930 (16)0.0242 (2)0.0561 (8)
C120.8438 (2)0.13368 (13)0.0541 (2)0.0450 (6)
C130.24802 (18)0.10372 (12)0.22012 (19)0.0391 (6)
C140.1691 (2)0.02767 (13)0.26309 (19)0.0446 (6)
C150.3566 (2)0.01971 (12)0.3664 (2)0.0445 (6)
C160.43736 (19)0.05594 (13)0.32484 (18)0.0414 (6)
C170.1354 (3)0.07709 (14)0.4323 (2)0.0608 (8)
H20.596 (2)0.2877 (13)0.159 (2)0.043 (6)*
H60.308200.035600.042500.0440*
H8A0.139700.108800.290900.0790*
H8B0.260900.066200.381700.0790*
H8C0.184300.021300.255200.0790*
H90.826300.281900.215800.0570*
H101.035100.234700.174700.0690*
H111.046000.138300.009500.0670*
H120.849600.095500.121400.0540*
H13A0.226700.145200.288400.0470*
H13B0.221600.123500.136200.0470*
H14A0.185700.012700.192300.0530*
H14B0.072300.039500.277500.0530*
H15A0.383800.040600.449300.0530*
H15B0.376800.060600.297000.0530*
H16A0.533900.043500.309400.0500*
H16B0.421800.096100.396000.0500*
H17A0.161700.094800.516300.0910*
H17B0.039500.065900.444400.0910*
H17C0.155600.118700.365600.0910*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0454 (3)0.0453 (3)0.0327 (3)0.0028 (2)0.0106 (2)0.0057 (2)
N10.0334 (8)0.0422 (8)0.0306 (8)0.0020 (6)0.0050 (6)0.0007 (6)
N20.0415 (9)0.0349 (8)0.0420 (9)0.0020 (7)0.0080 (7)0.0047 (7)
N30.0315 (8)0.0505 (9)0.0306 (8)0.0027 (6)0.0068 (6)0.0070 (7)
N40.0432 (9)0.0439 (9)0.0329 (8)0.0062 (7)0.0035 (7)0.0012 (7)
C10.0334 (9)0.0404 (10)0.0318 (9)0.0008 (7)0.0061 (7)0.0078 (7)
C20.0376 (10)0.0369 (9)0.0336 (9)0.0022 (7)0.0056 (7)0.0060 (7)
C30.0359 (9)0.0364 (9)0.0302 (9)0.0056 (7)0.0060 (7)0.0007 (7)
C40.0327 (9)0.0370 (9)0.0288 (8)0.0022 (7)0.0047 (7)0.0004 (7)
C50.0343 (9)0.0329 (9)0.0283 (8)0.0044 (7)0.0049 (7)0.0017 (7)
C60.0374 (9)0.0400 (10)0.0314 (9)0.0018 (7)0.0050 (7)0.0012 (7)
C70.0363 (9)0.0455 (10)0.0327 (9)0.0023 (8)0.0055 (7)0.0042 (8)
C80.0540 (13)0.0667 (14)0.0403 (11)0.0028 (10)0.0165 (9)0.0061 (10)
C90.0491 (12)0.0516 (12)0.0412 (11)0.0093 (9)0.0020 (9)0.0002 (9)
C100.0388 (11)0.0764 (16)0.0533 (13)0.0110 (10)0.0037 (9)0.0045 (12)
C110.0327 (10)0.0801 (16)0.0557 (13)0.0048 (10)0.0065 (9)0.0114 (12)
C120.0394 (10)0.0561 (12)0.0409 (10)0.0044 (9)0.0104 (8)0.0048 (9)
C130.0322 (9)0.0505 (11)0.0348 (9)0.0044 (8)0.0059 (7)0.0028 (8)
C140.0393 (10)0.0592 (13)0.0359 (10)0.0056 (9)0.0077 (8)0.0001 (9)
C150.0509 (12)0.0480 (11)0.0349 (10)0.0054 (9)0.0071 (8)0.0045 (8)
C160.0355 (10)0.0571 (12)0.0324 (9)0.0013 (8)0.0075 (7)0.0064 (8)
C170.0703 (16)0.0553 (14)0.0555 (14)0.0195 (12)0.0041 (11)0.0049 (11)
Geometric parameters (Å, º) top
S1—C31.7328 (18)C11—C121.384 (3)
S1—C71.737 (2)C13—C141.511 (3)
N1—C11.414 (2)C15—C161.512 (3)
N1—C51.295 (2)C6—H60.93
N2—C21.424 (2)C8—H8A0.96
N2—C31.394 (2)C8—H8B0.96
N3—C51.373 (2)C8—H8C0.96
N3—C131.461 (2)C9—H90.93
N3—C161.456 (2)C10—H100.93
N4—C141.459 (2)C11—H110.93
N4—C151.457 (3)C12—H120.93
N4—C171.459 (3)C13—H13A0.97
N2—H20.86 (2)C13—H13B0.97
C1—C121.398 (3)C14—H14A0.97
C1—C21.401 (3)C14—H14B0.97
C2—C91.386 (3)C15—H15A0.97
C3—C41.365 (2)C15—H15B0.97
C4—C51.473 (2)C16—H16A0.97
C4—C61.431 (3)C16—H16B0.97
C6—C71.350 (3)C17—H17A0.96
C7—C81.495 (3)C17—H17B0.96
C9—C101.378 (3)C17—H17C0.96
C10—C111.374 (3)
S1···N1i3.4699 (16)H8A···C10ix2.90
S1···C5i3.3870 (18)H8A···C11ix3.10
S1···H15Bii3.07H8A···H10ix2.53
S1···H13Ai3.19H8B···N4x2.69
N1···S1iii3.4699 (16)H8B···C15x2.93
N1···N2iii3.224 (2)H8B···H16Bx2.60
N2···N1i3.224 (2)H8C···H12ii2.35
N1···H2iii2.39 (2)H9···C1i3.00
N4···H8Biv2.69H9···C12i2.68
C5···S1iii3.3870 (18)H9···H12i2.59
C9···C12i3.592 (3)H10···H8Avi2.53
C12···C9iii3.592 (3)H11···H13Bvi2.43
C1···H9iii3.00H12···H8Cii2.35
C3···H15Bii3.08H12···H9iii2.59
C7···H16Aii3.03H13A···S1iii3.19
C9···H17Cii3.01H13B···H11ix2.43
C9···H17Av2.96H15A···C16vii3.07
C10···H8Avi2.90H15B···S1ii3.07
C11···H8Avi3.10H15B···C3ii3.08
C12···H9iii2.68H16A···C7ii3.03
C15···H8Biv2.93H16B···H8Biv2.60
C16···H15Avii3.07H16B···H2iii2.59
C16···H2iii3.04 (2)H17A···C9xi2.96
C17···H17Bviii3.09H17B···C17viii3.09
H2···N1i2.39 (2)H17B···H17Bviii2.52
H2···C16i3.04 (2)H17C···C9ii3.01
C3—S1—C791.93 (8)C7—C8—H8A109
C1—N1—C5122.90 (15)C7—C8—H8B110
C2—N2—C3115.43 (15)C7—C8—H8C110
C5—N3—C13124.25 (15)H8A—C8—H8B109
C5—N3—C16120.85 (15)H8A—C8—H8C109
C13—N3—C16111.19 (14)H8B—C8—H8C109
C14—N4—C15109.52 (15)C2—C9—H9119
C14—N4—C17111.49 (16)C10—C9—H9119
C15—N4—C17110.48 (17)C9—C10—H10120
C3—N2—H2113.3 (14)C11—C10—H10120
C2—N2—H2111.9 (13)C10—C11—H11120
N1—C1—C12115.88 (16)C12—C11—H11120
N1—C1—C2126.51 (16)C1—C12—H12119
C2—C1—C12117.29 (17)C11—C12—H12119
N2—C2—C9118.99 (17)N3—C13—H13A110
N2—C2—C1120.94 (16)N3—C13—H13B110
C1—C2—C9120.06 (17)C14—C13—H13A110
S1—C3—C4111.34 (13)C14—C13—H13B110
N2—C3—C4127.00 (16)H13A—C13—H13B108
S1—C3—N2121.55 (13)N4—C14—H14A110
C5—C4—C6125.77 (16)N4—C14—H14B110
C3—C4—C5122.27 (16)C13—C14—H14A110
C3—C4—C6111.93 (15)C13—C14—H14B110
N3—C5—C4116.10 (15)H14A—C14—H14B108
N1—C5—C4125.99 (15)N4—C15—H15A109
N1—C5—N3117.85 (15)N4—C15—H15B109
C4—C6—C7114.14 (16)C16—C15—H15A109
S1—C7—C6110.60 (14)C16—C15—H15B109
S1—C7—C8119.86 (14)H15A—C15—H15B108
C6—C7—C8129.54 (18)N3—C16—H16A110
C2—C9—C10121.44 (19)N3—C16—H16B110
C9—C10—C11119.38 (19)C15—C16—H16A110
C10—C11—C12119.75 (19)C15—C16—H16B110
C1—C12—C11122.04 (19)H16A—C16—H16B108
N3—C13—C14110.34 (16)N4—C17—H17A109
N4—C14—C13110.09 (16)N4—C17—H17B109
N4—C15—C16111.61 (16)N4—C17—H17C109
N3—C16—C15108.76 (16)H17A—C17—H17B110
C4—C6—H6123H17A—C17—H17C110
C7—C6—H6123H17B—C17—H17C109
C3—S1—C7—C61.07 (15)C12—C1—C2—C92.1 (3)
C3—S1—C7—C8179.21 (16)N1—C1—C12—C11172.14 (19)
C7—S1—C3—N2176.25 (15)C12—C1—C2—N2179.43 (17)
C7—S1—C3—C40.33 (14)N1—C1—C2—C9171.08 (18)
C5—N1—C1—C12141.50 (18)N1—C1—C2—N27.4 (3)
C1—N1—C5—N3169.28 (16)C1—C2—C9—C100.4 (3)
C5—N1—C1—C245.3 (3)N2—C2—C9—C10178.93 (19)
C1—N1—C5—C47.8 (3)N2—C3—C4—C57.2 (3)
C3—N2—C2—C9128.80 (19)S1—C3—C4—C61.6 (2)
C2—N2—C3—C451.1 (3)N2—C3—C4—C6174.77 (17)
C2—N2—C3—S1124.87 (15)S1—C3—C4—C5176.48 (13)
C3—N2—C2—C152.7 (2)C6—C4—C5—N1147.70 (18)
C13—N3—C16—C1557.3 (2)C6—C4—C5—N329.4 (3)
C16—N3—C13—C1458.1 (2)C3—C4—C5—N3148.39 (17)
C13—N3—C5—N1143.71 (17)C3—C4—C6—C72.5 (2)
C16—N3—C5—C4164.67 (16)C5—C4—C6—C7175.49 (17)
C5—N3—C16—C15143.48 (17)C3—C4—C5—N134.5 (3)
C5—N3—C13—C14143.57 (17)C4—C6—C7—C8178.13 (19)
C16—N3—C5—N112.7 (3)C4—C6—C7—S12.2 (2)
C13—N3—C5—C439.0 (2)C2—C9—C10—C111.7 (3)
C15—N4—C14—C1357.9 (2)C9—C10—C11—C122.0 (3)
C14—N4—C15—C1659.0 (2)C10—C11—C12—C10.3 (3)
C17—N4—C15—C16177.85 (15)N3—C13—C14—N457.8 (2)
C17—N4—C14—C13179.55 (17)N4—C15—C16—N358.2 (2)
C2—C1—C12—C111.7 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z; (iii) x, y+1/2, z1/2; (iv) x, y, z1; (v) x+1, y+1/2, z1/2; (vi) x+1, y, z; (vii) x+1, y, z1; (viii) x, y, z1; (ix) x1, y, z; (x) x, y, z+1; (xi) x+1, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.86 (2)2.39 (2)3.224 (2)165 (2)
C8—H8B···N4x0.962.69 (1)3.466 (2)138
Symmetry codes: (i) x, y+1/2, z+1/2; (x) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H20N4S
Mr312.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.9130 (8), 16.5329 (13), 9.9992 (8)
β (°) 98.023 (1)
V3)1622.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.942, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
16674, 3202, 2963
Rint0.026
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.119, 1.12
No. of reflections3202
No. of parameters205
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.86 (2)2.39 (2)3.224 (2)165 (2)
C8—H8B···N4ii0.962.69 (1)3.466 (2)138
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y, z+1.
 

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