4-Amino-N-(4,6-di­methyl­pyrimidin-2-yl)benzene­sulfonamide–1,4-di­aza­bicyclo­[2.2.2]octane (2/1)

Arman, H.D.; Kaulgud, T.; Tiekink, E.R.T.

doi:10.1107/S1600536813027037

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1615

doi:10.1107/S1600536813027037

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4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–1,4-diazabicyclo[2.2.2]octane (2/1)

Hadi D. Arman,^a Trupta Kaulgud ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 30 September 2013; accepted 1 October 2013; online 5 October 2013)

The asymmetric unit of the title co-crystal, C₁₂H₁₄N₄O₂S·0.5C₆H₁₂N₂, comprises the sulfonamide molecule and half a molecule of 1,4-diazabicyclo[2.2.2]octane (DABCO), the latter being disposed about a crystallographic twofold rotation axis. In the sulfonamide molecule, the aromatic rings are almost perpendicular to one another [dihedral angle = 75.01 (8)°]. In the crystal, molecules are connected into a three-molecule aggregate via amide–DABCO N—H⋯N hydrogen bonds, and these are connected into a three-dimensional architecture via amino–DABCO N—H⋯O and amino-pyrimidine N—H⋯N hydrogen bonds.

CCDC reference: 964340

Related literature

For the structure of the sulfonamide, see: Tiwari et al. (1984 ). For related studies of co-crystal formation, see: Ellis et al. (2009 ); Arman & Tiekink (2013 ). For co-crystals of the sulfonamide with carboxylic acids, see: Arman et al. (2010 ); Ghosh et al. (2011 ); Smith & Wermuth (2013 ).

Experimental

Crystal data

C₁₂H₁₄N₄O₂S·0.5C₆H₁₂N₂
M_r = 334.42
Orthorhombic, P b c n
a = 26.488 (3) Å
b = 9.7886 (11) Å
c = 12.2163 (13) Å
V = 3167.4 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 98 K
0.35 × 0.31 × 0.21 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
7965 measured reflections
3616 independent reflections
3264 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.115
S = 0.99
3616 reflections
219 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N5ⁱ	0.88 (2)	1.90 (2)	2.768 (2)	169 (2)
N4—H2N⋯O2ⁱⁱ	0.88 (1)	2.48 (2)	3.058 (2)	124 (2)
N4—H2N⋯N2ⁱⁱ	0.88 (1)	2.59 (2)	3.376 (2)	149 (2)
N4—H3N⋯O1ⁱⁱⁱ	0.88 (2)	2.15 (2)	3.032 (2)	178 (2)
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 964340

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536813027037/su2652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813027037/su2652Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813027037/su2652Isup3.cml

checkCIF report

Comment top

The title co-crystal was formed in continuation of on-going structural studies of co-crystals (Ellis et al., 2009; Arman & Tiekink, 2013). While co-crystals of the title sulfonamide with carboxylic acids are known (Arman, et al. 2010; Ghosh et al. 2011; Smith & Wermuth, 2013), the present investigation appears to be the first describing a co-crystal of the sulfonamide with an amine.

The asymmetric unit of the title compound contains a molecule of the sulfonamide in a general position, and half a molecule of 1,4-diazabicyclo[2.2.2]octane (DABCO) which is disposed about a crystallographic two-fold rotation axis, Fig. 1. The overall shape of the sulfonamide approximates the letter L with the dihedral angle between the two aromatic rings being 75.01 (8)°, which compares to 78.1 (6)° found in the parent sulfonamide compound (Tiwari et al., 1984). However, this is a little misleading as there is a difference in the conformation of the two sulfonamides. In the title sulfonamide the SOC₆H₄NH₂ residue lies to one side of the pyrimidinyl ring with the remaining O atom, O2, being co-planar giving the L-shape, whereas in the parent sulfonamide (Tiwari et al., 1984) the SO₂ O atoms lie to one side of the pyrimidinyl ring and the C₆H₄NH₂ residue to the other.

A three-dimensional architecture is formed in the crystal structure by N—H···O and N-H···N hydrogen bonds (Fig. 2 and Table 1). The amide group, N1—H1N, forms a hydrogen bond to a DABCO N atom, N5, so that a three-molecule aggregate results. The amino group H atom, N4—H2N, is bifurcated, forming hydrogen bonds to the sulfonamide atom O2 and to the pyrimidinyl atom N2. The second amino group H atom, N4—H3N, forms a hydrogen bond to the second sulfonamide O atom, O1.

Related literature top

For the structure of the sulfonamide, see: Tiwari et al. (1984). For related studies of co-crystal formation, see: Ellis et al. (2009); Arman & Tiekink (2013). For co-crystals of the sulfonamide with carboxylic acids, see: Arman et al. (2010); Ghosh et al. (2011); Smith & Wermuth (2013).

Experimental top

Crystals of the title compound were obtained by the co-crystallization of the sulfonamide (ACROS, 0.18 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO; Sigma-Aldrich, 0.10 mmol) in methanol. Block-like colourless crystals were obtained by slow evaporation (M.p. = 479–485 K).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structures of the components of the title compound, with atom labelling: (a) the sulfonamide and (b) DABCO. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A viewed in projection along the c axis of the crystal packing of the title compound. The N-H···O and N-H···N hydrogen bonds are shown as orange and blue dashed lines, respectively.

4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–1,4-diazabicyclo[2.2.2]octane (2/1) top

Crystal data top

C₁₂H₁₄N₄O₂S·0.5C₆H₁₂N₂	F(000) = 1416
M_r = 334.42	D_x = 1.403 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 11130 reflections
a = 26.488 (3) Å	θ = 2.1–40.3°
b = 9.7886 (11) Å	µ = 0.22 mm⁻¹
c = 12.2163 (13) Å	T = 98 K
V = 3167.4 (6) Å³	Block, colourless
Z = 8	0.35 × 0.31 × 0.21 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −10→34
7965 measured reflections	k = −8→12
3616 independent reflections	l = −15→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0551P)² + 2.7774P] where P = (F_o² + 2F_c²)/3
3616 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.41 e Å⁻³
3 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₂H₁₄N₄O₂S·0.5C₆H₁₂N₂	V = 3167.4 (6) Å³
M_r = 334.42	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 26.488 (3) Å	µ = 0.22 mm⁻¹
b = 9.7886 (11) Å	T = 98 K
c = 12.2163 (13) Å	0.35 × 0.31 × 0.21 mm

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3264 reflections with I > 2σ(I)
7965 measured reflections	R_int = 0.032
3616 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.41 e Å⁻³
3616 reflections	Δρ_min = −0.48 e Å⁻³
219 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.132415 (15)	0.06565 (4)	0.45540 (3)	0.01333 (12)
O1	0.11533 (5)	−0.05810 (12)	0.50942 (10)	0.0173 (3)
O2	0.13901 (5)	0.05841 (13)	0.33849 (10)	0.0183 (3)
N1	0.09018 (5)	0.17725 (15)	0.48968 (11)	0.0148 (3)
H1N	0.0745 (7)	0.152 (2)	0.5494 (11)	0.018*
N2	0.12538 (5)	0.36203 (15)	0.39075 (11)	0.0160 (3)
N3	0.07074 (6)	0.39389 (15)	0.54545 (11)	0.0160 (3)
N4	0.32337 (6)	0.25427 (17)	0.65547 (13)	0.0218 (3)
H2N	0.3284 (9)	0.250 (2)	0.7267 (8)	0.026*
H3N	0.3418 (8)	0.308 (2)	0.6139 (16)	0.026*
C1	0.09647 (6)	0.31690 (17)	0.47297 (13)	0.0148 (3)
C2	0.12939 (6)	0.49905 (19)	0.38156 (14)	0.0166 (3)
C3	0.10504 (7)	0.58644 (18)	0.45383 (14)	0.0181 (4)
H3	0.1085	0.6827	0.4474	0.022*
C4	0.07545 (7)	0.52934 (18)	0.53588 (14)	0.0169 (3)
C5	0.16111 (8)	0.55243 (19)	0.28925 (15)	0.0226 (4)
H5A	0.1968	0.5353	0.3050	0.034*
H5B	0.1555	0.6509	0.2812	0.034*
H5C	0.1517	0.5060	0.2212	0.034*
C6	0.04783 (7)	0.61545 (19)	0.61820 (15)	0.0223 (4)
H6A	0.0120	0.5909	0.6180	0.033*
H6B	0.0515	0.7122	0.5990	0.033*
H6C	0.0620	0.5995	0.6912	0.033*
C7	0.18946 (6)	0.11773 (17)	0.51417 (13)	0.0144 (3)
C8	0.19655 (6)	0.10442 (17)	0.62712 (14)	0.0159 (3)
H8	0.1710	0.0640	0.6712	0.019*
C9	0.24078 (6)	0.15020 (18)	0.67437 (14)	0.0173 (3)
H9	0.2456	0.1396	0.7509	0.021*
C10	0.27886 (7)	0.21239 (18)	0.61103 (14)	0.0172 (3)
C11	0.27024 (7)	0.2272 (2)	0.49774 (15)	0.0211 (4)
H11	0.2950	0.2707	0.4535	0.025*
C12	0.22649 (7)	0.17962 (19)	0.45039 (14)	0.0192 (4)
H12	0.2216	0.1890	0.3737	0.023*
N5	0.02978 (6)	0.88272 (15)	0.16824 (11)	0.0165 (3)
C13	0.05365 (6)	0.80970 (18)	0.26139 (13)	0.0168 (3)
H13A	0.0862	0.8535	0.2799	0.020*
H13B	0.0604	0.7137	0.2407	0.020*
C14	0.01889 (8)	1.02566 (18)	0.20149 (15)	0.0234 (4)
H14A	0.0043	1.0765	0.1389	0.028*
H14B	0.0506	1.0716	0.2236	0.028*
C15	−0.01819 (6)	0.81388 (19)	0.13850 (14)	0.0180 (3)
H15A	−0.0111	0.7197	0.1133	0.022*
H15B	−0.0347	0.8639	0.0779	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0140 (2)	0.0121 (2)	0.0139 (2)	−0.00069 (14)	0.00026 (15)	−0.00111 (14)
O1	0.0176 (6)	0.0125 (6)	0.0219 (6)	−0.0016 (5)	0.0005 (5)	0.0000 (5)
O2	0.0206 (6)	0.0201 (6)	0.0142 (6)	−0.0009 (5)	0.0005 (5)	−0.0043 (5)
N1	0.0135 (6)	0.0136 (7)	0.0174 (6)	−0.0002 (5)	0.0036 (5)	0.0003 (5)
N2	0.0162 (7)	0.0152 (7)	0.0166 (7)	0.0004 (5)	0.0013 (6)	0.0005 (6)
N3	0.0162 (7)	0.0162 (7)	0.0157 (6)	0.0013 (6)	0.0006 (5)	−0.0005 (5)
N4	0.0188 (7)	0.0266 (8)	0.0198 (7)	−0.0053 (6)	−0.0043 (6)	0.0018 (6)
C1	0.0123 (7)	0.0162 (8)	0.0158 (7)	0.0002 (6)	−0.0018 (6)	0.0000 (6)
C2	0.0150 (7)	0.0174 (8)	0.0174 (8)	0.0003 (6)	−0.0006 (6)	0.0022 (7)
C3	0.0188 (8)	0.0132 (7)	0.0225 (9)	0.0012 (6)	−0.0007 (7)	0.0011 (6)
C4	0.0158 (8)	0.0172 (8)	0.0176 (8)	0.0027 (6)	−0.0017 (6)	−0.0012 (6)
C5	0.0255 (9)	0.0181 (8)	0.0243 (9)	−0.0014 (7)	0.0057 (8)	0.0028 (7)
C6	0.0246 (9)	0.0188 (8)	0.0234 (9)	0.0047 (7)	0.0034 (7)	−0.0024 (7)
C7	0.0121 (7)	0.0140 (7)	0.0171 (7)	−0.0002 (6)	−0.0002 (6)	−0.0008 (6)
C8	0.0162 (8)	0.0155 (8)	0.0160 (7)	−0.0004 (6)	0.0034 (6)	0.0001 (6)
C9	0.0181 (8)	0.0181 (8)	0.0157 (7)	0.0007 (7)	−0.0015 (6)	−0.0012 (6)
C10	0.0154 (8)	0.0156 (8)	0.0204 (8)	−0.0002 (6)	−0.0008 (7)	0.0006 (7)
C11	0.0163 (8)	0.0255 (9)	0.0214 (8)	−0.0039 (7)	0.0018 (7)	0.0064 (7)
C12	0.0154 (8)	0.0251 (9)	0.0172 (8)	−0.0008 (7)	−0.0005 (7)	0.0053 (7)
N5	0.0166 (7)	0.0174 (7)	0.0154 (6)	−0.0021 (6)	0.0007 (5)	0.0016 (6)
C13	0.0151 (8)	0.0194 (8)	0.0159 (7)	0.0004 (6)	−0.0001 (6)	−0.0003 (6)
C14	0.0300 (10)	0.0144 (8)	0.0258 (9)	−0.0003 (7)	0.0000 (8)	0.0028 (7)
C15	0.0141 (7)	0.0234 (9)	0.0165 (7)	−0.0010 (7)	−0.0009 (6)	−0.0013 (7)

Geometric parameters (Å, º) top

S1—O2	1.4406 (12)	C6—H6C	0.9800
S1—O1	1.4518 (12)	C7—C12	1.392 (2)
S1—N1	1.6188 (14)	C7—C8	1.399 (2)
S1—C7	1.7488 (17)	C8—C9	1.381 (2)
N1—C1	1.392 (2)	C8—H8	0.9500
N1—H1N	0.876 (9)	C9—C10	1.409 (2)
N2—C1	1.338 (2)	C9—H9	0.9500
N2—C2	1.350 (2)	C10—C11	1.410 (2)
N3—C4	1.337 (2)	C11—C12	1.377 (2)
N3—C1	1.348 (2)	C11—H11	0.9500
N4—C10	1.361 (2)	C12—H12	0.9500
N4—H2N	0.881 (9)	N5—C15	1.483 (2)
N4—H3N	0.877 (10)	N5—C14	1.485 (2)
C2—C3	1.388 (2)	N5—C13	1.485 (2)
C2—C5	1.500 (2)	C13—C15ⁱ	1.542 (2)
C3—C4	1.390 (2)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C6	1.502 (2)	C14—C14ⁱ	1.551 (4)
C5—H5A	0.9800	C14—H14A	0.9900
C5—H5B	0.9800	C14—H14B	0.9900
C5—H5C	0.9800	C15—C13ⁱ	1.542 (2)
C6—H6A	0.9800	C15—H15A	0.9900
C6—H6B	0.9800	C15—H15B	0.9900

O2—S1—O1	116.57 (7)	C12—C7—S1	120.40 (13)
O2—S1—N1	111.93 (8)	C8—C7—S1	119.60 (13)
O1—S1—N1	103.30 (7)	C9—C8—C7	119.74 (16)
O2—S1—C7	108.46 (8)	C9—C8—H8	120.1
O1—S1—C7	109.02 (8)	C7—C8—H8	120.1
N1—S1—C7	107.11 (8)	C8—C9—C10	121.19 (15)
C1—N1—S1	122.82 (12)	C8—C9—H9	119.4
C1—N1—H1N	117.0 (14)	C10—C9—H9	119.4
S1—N1—H1N	110.8 (14)	N4—C10—C11	120.04 (16)
C1—N2—C2	115.81 (15)	N4—C10—C9	122.07 (16)
C4—N3—C1	116.74 (15)	C11—C10—C9	117.86 (16)
C10—N4—H2N	120.7 (15)	C12—C11—C10	120.92 (16)
C10—N4—H3N	115.6 (15)	C12—C11—H11	119.5
H2N—N4—H3N	121 (2)	C10—C11—H11	119.5
N2—C1—N3	126.72 (16)	C11—C12—C7	120.37 (16)
N2—C1—N1	120.18 (15)	C11—C12—H12	119.8
N3—C1—N1	113.09 (15)	C7—C12—H12	119.8
N2—C2—C3	121.51 (16)	C15—N5—C14	109.18 (14)
N2—C2—C5	116.91 (15)	C15—N5—C13	109.49 (13)
C3—C2—C5	121.58 (16)	C14—N5—C13	109.06 (13)
C2—C3—C4	118.22 (16)	N5—C13—C15ⁱ	109.61 (13)
C2—C3—H3	120.9	N5—C13—H13A	109.7
C4—C3—H3	120.9	C15ⁱ—C13—H13A	109.7
N3—C4—C3	120.97 (16)	N5—C13—H13B	109.7
N3—C4—C6	116.90 (16)	C15ⁱ—C13—H13B	109.7
C3—C4—C6	122.13 (16)	H13A—C13—H13B	108.2
C2—C5—H5A	109.5	N5—C14—C14ⁱ	109.52 (9)
C2—C5—H5B	109.5	N5—C14—H14A	109.8
H5A—C5—H5B	109.5	C14ⁱ—C14—H14A	109.8
C2—C5—H5C	109.5	N5—C14—H14B	109.8
H5A—C5—H5C	109.5	C14ⁱ—C14—H14B	109.8
H5B—C5—H5C	109.5	H14A—C14—H14B	108.2
C4—C6—H6A	109.5	N5—C15—C13ⁱ	109.84 (13)
C4—C6—H6B	109.5	N5—C15—H15A	109.7
H6A—C6—H6B	109.5	C13ⁱ—C15—H15A	109.7
C4—C6—H6C	109.5	N5—C15—H15B	109.7
H6A—C6—H6C	109.5	C13ⁱ—C15—H15B	109.7
H6B—C6—H6C	109.5	H15A—C15—H15B	108.2
C12—C7—C8	119.89 (15)

O2—S1—N1—C1	−66.25 (15)	O2—S1—C7—C8	−166.16 (13)
O1—S1—N1—C1	167.54 (13)	O1—S1—C7—C8	−38.28 (16)
C7—S1—N1—C1	52.51 (15)	N1—S1—C7—C8	72.86 (15)
C2—N2—C1—N3	1.0 (3)	C12—C7—C8—C9	−1.4 (3)
C2—N2—C1—N1	−179.64 (15)	S1—C7—C8—C9	−177.55 (13)
C4—N3—C1—N2	−1.6 (3)	C7—C8—C9—C10	1.0 (3)
C4—N3—C1—N1	179.01 (15)	C8—C9—C10—N4	−177.89 (17)
S1—N1—C1—N2	28.3 (2)	C8—C9—C10—C11	0.4 (3)
S1—N1—C1—N3	−152.26 (12)	N4—C10—C11—C12	176.87 (18)
C1—N2—C2—C3	0.3 (2)	C9—C10—C11—C12	−1.5 (3)
C1—N2—C2—C5	−179.32 (15)	C10—C11—C12—C7	1.1 (3)
N2—C2—C3—C4	−1.0 (3)	C8—C7—C12—C11	0.3 (3)
C5—C2—C3—C4	178.66 (16)	S1—C7—C12—C11	176.48 (15)
C1—N3—C4—C3	0.8 (2)	C15—N5—C13—C15ⁱ	−61.24 (15)
C1—N3—C4—C6	−178.58 (15)	C14—N5—C13—C15ⁱ	58.17 (18)
C2—C3—C4—N3	0.4 (3)	C15—N5—C14—C14ⁱ	57.7 (2)
C2—C3—C4—C6	179.74 (16)	C13—N5—C14—C14ⁱ	−61.9 (2)
O2—S1—C7—C12	17.69 (17)	C14—N5—C15—C13ⁱ	−61.68 (17)
O1—S1—C7—C12	145.57 (14)	C13—N5—C15—C13ⁱ	57.66 (16)
N1—S1—C7—C12	−103.29 (15)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5ⁱⁱ	0.88 (2)	1.90 (2)	2.768 (2)	169 (2)
N4—H2N···O2ⁱⁱⁱ	0.88 (1)	2.48 (2)	3.058 (2)	124 (2)
N4—H2N···N2ⁱⁱⁱ	0.88 (1)	2.59 (2)	3.376 (2)	149 (2)
N4—H3N···O1^iv	0.88 (2)	2.15 (2)	3.032 (2)	178 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5ⁱ	0.875 (15)	1.904 (16)	2.768 (2)	168.9 (17)
N4—H2N···O2ⁱⁱ	0.881 (11)	2.475 (18)	3.058 (2)	124.2 (16)
N4—H2N···N2ⁱⁱ	0.881 (11)	2.592 (16)	3.376 (2)	148.8 (18)
N4—H3N···O1ⁱⁱⁱ	0.88 (2)	2.15 (2)	3.032 (2)	178.1 (19)

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

Acknowledgements

We are grateful to the Ministry of Higher Education (Malaysia) and the University of Malaya (UM) for funding structural studies through the High-Impact Research scheme (UM·C/HIR-MOHE/SC/03).

References

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Volume 69| Part 11| November 2013| Page o1615

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Amino-N-(4,6-di­methyl­pyrimidin-2-yl)benzene­sulfonamide–1,4-di­aza­bi­cyclo­[2.2.2]octane (2/1)

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4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide–1,4-diazabicyclo[2.2.2]octane (2/1)