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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o631-o632
https://doi.org/10.1107/S2056989015014115

Crystal structure of cyclo­sulfamuron

Gihaeng Kang,a Jineun Kim,a* Eunjin Kwona and Tae Ho Kima*

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 July 2015; accepted 27 July 2015; online 31 July 2015)

The title compound (systematic name: 1-{[2-(cyclo­propylcarbon­yl)anilino]sulfon­yl}-3-(4,6-di­meth­oxy­pyrimidin-2-yl)urea), C17H19N5O6S, is a pyrimidinyl­sulfonyl­urea herbicide. The dihedral angles between the mean planes of the central benzene ring and the cyclo­propyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. The C atoms of the meth­oxy groups lie almost in the plane of the pyrimidine ring [deviations = 0.043 (2) and 0.028 (2) Å] and intra­molecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds all close S(6) rings. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds and weak π–π inter­actions [centroid–centroid distances = 3.6175 (9) and 3.7068 (9) Å] link adjacent mol­ecules, forming a three-dimensional network.

CCDC reference: 1415211

Similar articles

1. Related literature

For information on the herbicidal properties of the title compound, see: Sarıgül & İnam (2009[Sarıgül, T. & İnam, R. (2009). Electrochim. Acta, 54, 5376-5380.]). For a related crystal structure, see: Xia et al. (2008[Xia, J., Li, F., Yin, L., Yu, D. & Wu, D. (2008). Acta Cryst. E64, o632.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H19N5O6S

  • Mr = 421.43

  • Monoclinic, P 21 /n

  • a = 12.7019 (4) Å

  • b = 9.6216 (3) Å

  • c = 15.6213 (5) Å

  • β = 93.6194 (12)°

  • V = 1905.31 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 173 K

  • 0.32 × 0.27 × 0.23 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.934, Tmax = 0.952

  • 17544 measured reflections

  • 4365 independent reflections

  • 3688 reflections with I > 2σ(I)

  • Rint = 0.030

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.113

  • S = 1.05

  • 4365 reflections

  • 264 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.88 1.86 2.5736 (18) 137
N2—H2N⋯N4 0.88 1.92 2.6158 (18) 135
C9—H9⋯O3 0.95 2.45 3.088 (2) 124
N3—H3N⋯O2i 0.88 2.08 2.9391 (17) 165
C2—H2B⋯O2ii 0.99 2.51 3.483 (2) 169
C3—H3⋯O4iii 1.00 2.51 3.286 (2) 135
C8—H8⋯O3iv 0.95 2.50 3.307 (2) 142
Symmetry codes: (i) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z; (iv) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

CCDC reference: 1415211

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015014115/hb7470sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014115/hb7470Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014115/hb7470Isup3.cml

checkCIF report


Comment top

Cyclosulfamuron [systematic name: 1-[2-(cyclopropylcarbonyl)anilinosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea] is a pyrimidinylsulfonylurea herbicide and has been widely used to control weeds because of their low toxicity to mammals and their high herbicidal activity (Sarıgül & Inam, 2009). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angles between the mean planes of the central phenyl ring and the cyclopropyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Xia et al., 2008).

In the crystal structure (Fig. 2), N—H···O and C—H···O hydrogen bonds are observed (Table 1). In addition, weak intermolecular Cg1···Cg1v and Cg1···Cg2vi (Cg1 and Cg2 are the centroids of the N4—C12—N5—C15—C14—C13 and C5–C10 rings, respectively) interactions are present [for symmetry codes: (v), -x + 2, -y, -z + 1, (vi), x + 1/2, -y + 1/2, z + 1/2]. A three-dimensional network is formed by the hydrogen bonds and π–π interactions.

Related literature top

For information on the herbicidal properties of the title compound, see: Sarıgül & Inam (2009). For a related crystal structure, see: Xia et al. (2008).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(N—H) = 0.88 Å, Uiso = 1.2Ueq(C) for N—H group, d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H. d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 group, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Structure description top

Cyclosulfamuron [systematic name: 1-[2-(cyclopropylcarbonyl)anilinosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea] is a pyrimidinylsulfonylurea herbicide and has been widely used to control weeds because of their low toxicity to mammals and their high herbicidal activity (Sarıgül & Inam, 2009). However, until now its crystal structure has not been reported. In the title compound (Fig. 1), the dihedral angles between the mean planes of the central phenyl ring and the cyclopropyl and pyrimidinyl rings are 75.32 (9) and 88.79 (4)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Xia et al., 2008).

In the crystal structure (Fig. 2), N—H···O and C—H···O hydrogen bonds are observed (Table 1). In addition, weak intermolecular Cg1···Cg1v and Cg1···Cg2vi (Cg1 and Cg2 are the centroids of the N4—C12—N5—C15—C14—C13 and C5–C10 rings, respectively) interactions are present [for symmetry codes: (v), -x + 2, -y, -z + 1, (vi), x + 1/2, -y + 1/2, z + 1/2]. A three-dimensional network is formed by the hydrogen bonds and π–π interactions.

For information on the herbicidal properties of the title compound, see: Sarıgül & Inam (2009). For a related crystal structure, see: Xia et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing viewed along the c axis. The intermolecular interactions are shown as dashed lines.
1-{[2-(Cyclopropylcarbonyl)anilino]sulfonyl}-3-(4,6-dimethoxypyrimidin-2-yl)urea top
Crystal data top
C17H19N5O6SF(000) = 880
Mr = 421.43Dx = 1.469 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.7019 (4) ÅCell parameters from 6977 reflections
b = 9.6216 (3) Åθ = 2.6–27.4°
c = 15.6213 (5) ŵ = 0.22 mm−1
β = 93.6194 (12)°T = 173 K
V = 1905.31 (10) Å3Block, colourless
Z = 40.32 × 0.27 × 0.23 mm
Data collection top
Bruker APEXII CCD
diffractometer		3688 reflections with I > 2σ(I)
φ and ω scansRint = 0.030
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 27.5°, θmin = 2.0°
Tmin = 0.934, Tmax = 0.952h = −16→15
17544 measured reflectionsk = −12→12
4365 independent reflectionsl = −20→20
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.7248P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4365 reflectionsΔρmax = 0.22 e Å−3
264 parametersΔρmin = −0.49 e Å−3
Crystal data top
C17H19N5O6SV = 1905.31 (10) Å3
Mr = 421.43Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.7019 (4) ŵ = 0.22 mm−1
b = 9.6216 (3) ÅT = 173 K
c = 15.6213 (5) Å0.32 × 0.27 × 0.23 mm
β = 93.6194 (12)°
Data collection top
Bruker APEXII CCD
diffractometer		4365 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		3688 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.952Rint = 0.030
17544 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.05Δρmax = 0.22 e Å−3
4365 reflectionsΔρmin = −0.49 e Å−3
264 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.03274 (3)0.41778 (4)0.19915 (2)0.02564 (12)
O11.02757 (11)0.25129 (16)−0.03440 (8)0.0524 (4)
O21.12410 (9)0.48608 (12)0.17159 (7)0.0340 (3)
O30.95254 (9)0.49585 (12)0.23699 (7)0.0343 (3)
O41.19071 (9)0.18921 (12)0.19997 (7)0.0335 (3)
O50.94327 (9)0.31556 (13)0.52112 (7)0.0386 (3)
O61.17908 (10)−0.04334 (14)0.61128 (7)0.0429 (3)
N10.98567 (10)0.33405 (14)0.11638 (8)0.0290 (3)
H1N1.01870.34560.06900.035*
N21.06665 (10)0.30293 (14)0.27345 (8)0.0281 (3)
H2N1.03170.30140.32030.034*
N31.17533 (10)0.13526 (15)0.33969 (8)0.0303 (3)
H3N1.22790.07670.33510.036*
N41.05707 (10)0.22678 (14)0.43352 (8)0.0284 (3)
N51.17993 (10)0.04736 (14)0.47520 (8)0.0302 (3)
C11.00581 (16)0.0853 (2)−0.18258 (11)0.0418 (4)
H1A1.06950.1442−0.17400.050*
H1B1.0162−0.0019−0.21470.050*
C20.90252 (18)0.1560 (2)−0.19567 (11)0.0492 (5)
H2A0.84860.1127−0.23570.059*
H2B0.90190.2589−0.19500.059*
C30.93094 (14)0.08205 (17)−0.11251 (10)0.0354 (4)
H30.8943−0.0082−0.10310.042*
C40.95231 (14)0.17112 (17)−0.03618 (10)0.0334 (4)
C50.88087 (12)0.16383 (17)0.03524 (10)0.0301 (3)
C60.79319 (14)0.0755 (2)0.02989 (12)0.0415 (4)
H60.77970.0215−0.02060.050*
C70.72575 (15)0.0639 (2)0.09523 (13)0.0462 (5)
H70.66720.00230.09010.055*
C80.74454 (14)0.1432 (2)0.16818 (12)0.0432 (4)
H80.69870.13540.21370.052*
C90.82919 (13)0.23370 (19)0.17609 (10)0.0347 (4)
H90.84030.28860.22640.042*
C100.89805 (12)0.24451 (16)0.11062 (9)0.0267 (3)
C111.14737 (12)0.20858 (16)0.26595 (9)0.0267 (3)
C121.13446 (12)0.13831 (16)0.42007 (9)0.0272 (3)
C131.01967 (12)0.22237 (17)0.51212 (9)0.0294 (3)
C141.05796 (13)0.13144 (18)0.57482 (9)0.0325 (4)
H141.03030.12740.62990.039*
C151.13996 (13)0.04587 (18)0.55188 (10)0.0314 (3)
C160.89737 (16)0.3201 (2)0.60284 (11)0.0514 (5)
H16A0.86050.23260.61240.077*
H16B0.84720.39740.60350.077*
H16C0.95310.33360.64840.077*
C171.26553 (16)−0.1300 (2)0.58797 (12)0.0463 (5)
H17A1.2435−0.18510.53720.069*
H17B1.2862−0.19250.63570.069*
H17C1.3256−0.07140.57520.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0234 (2)0.0291 (2)0.02454 (19)−0.00228 (14)0.00254 (14)−0.00382 (13)
O10.0535 (9)0.0729 (10)0.0323 (6)−0.0295 (7)0.0133 (6)−0.0169 (6)
O20.0313 (6)0.0348 (6)0.0362 (6)−0.0109 (5)0.0052 (5)−0.0047 (5)
O30.0321 (6)0.0368 (6)0.0343 (6)0.0076 (5)0.0039 (5)−0.0045 (5)
O40.0305 (6)0.0445 (7)0.0263 (5)0.0045 (5)0.0096 (4)−0.0049 (5)
O50.0368 (7)0.0544 (8)0.0255 (6)0.0162 (6)0.0090 (5)−0.0010 (5)
O60.0459 (8)0.0518 (8)0.0309 (6)0.0133 (6)0.0007 (5)0.0070 (5)
N10.0263 (7)0.0387 (7)0.0222 (6)−0.0083 (6)0.0039 (5)−0.0029 (5)
N20.0243 (7)0.0385 (7)0.0221 (6)0.0048 (5)0.0055 (5)−0.0010 (5)
N30.0256 (7)0.0394 (7)0.0263 (6)0.0096 (6)0.0059 (5)−0.0015 (5)
N40.0253 (7)0.0370 (7)0.0232 (6)0.0037 (5)0.0039 (5)−0.0023 (5)
N50.0263 (7)0.0368 (7)0.0274 (6)0.0026 (6)0.0016 (5)−0.0017 (5)
C10.0512 (11)0.0429 (10)0.0312 (8)0.0058 (8)0.0010 (8)−0.0081 (7)
C20.0760 (15)0.0388 (10)0.0310 (9)0.0193 (10)−0.0112 (9)−0.0048 (7)
C30.0467 (10)0.0305 (8)0.0283 (8)0.0018 (7)−0.0033 (7)−0.0030 (6)
C40.0368 (9)0.0366 (9)0.0262 (7)−0.0024 (7)−0.0031 (6)−0.0015 (6)
C50.0270 (8)0.0333 (8)0.0292 (7)−0.0029 (6)−0.0049 (6)0.0009 (6)
C60.0348 (10)0.0436 (10)0.0451 (10)−0.0099 (8)−0.0048 (8)−0.0083 (8)
C70.0301 (9)0.0511 (11)0.0571 (11)−0.0163 (8)−0.0002 (8)−0.0050 (9)
C80.0282 (9)0.0552 (11)0.0471 (10)−0.0093 (8)0.0086 (7)0.0018 (9)
C90.0255 (8)0.0450 (10)0.0338 (8)−0.0062 (7)0.0027 (6)−0.0025 (7)
C100.0220 (7)0.0304 (8)0.0272 (7)−0.0022 (6)−0.0019 (6)0.0015 (6)
C110.0209 (7)0.0342 (8)0.0252 (7)−0.0015 (6)0.0030 (5)−0.0046 (6)
C120.0234 (7)0.0346 (8)0.0238 (7)−0.0015 (6)0.0017 (6)−0.0037 (6)
C130.0260 (8)0.0379 (8)0.0244 (7)0.0015 (6)0.0033 (6)−0.0057 (6)
C140.0328 (9)0.0429 (9)0.0220 (7)0.0020 (7)0.0036 (6)−0.0029 (6)
C150.0287 (8)0.0383 (9)0.0270 (7)−0.0005 (7)−0.0013 (6)−0.0006 (6)
C160.0513 (12)0.0780 (15)0.0262 (8)0.0277 (11)0.0122 (8)−0.0043 (9)
C170.0476 (11)0.0523 (11)0.0379 (9)0.0167 (9)−0.0058 (8)0.0016 (8)
Geometric parameters (Å, º) top
S1—O21.4237 (11)C2—C31.505 (2)
S1—O31.4238 (11)C2—H2A0.9900
S1—N11.6065 (12)C2—H2B0.9900
S1—N21.6402 (13)C3—C41.480 (2)
O1—C41.227 (2)C3—H31.0000
O4—C111.2132 (17)C4—C51.484 (2)
O5—C131.3351 (19)C5—C61.399 (2)
O5—C161.4372 (19)C5—C101.416 (2)
O6—C151.3366 (19)C6—C71.378 (3)
O6—C171.444 (2)C6—H60.9500
N1—C101.4058 (19)C7—C81.379 (3)
N1—H1N0.8800C7—H70.9500
N2—C111.3799 (19)C8—C91.383 (2)
N2—H2N0.8800C8—H80.9500
N3—C111.378 (2)C9—C101.391 (2)
N3—C121.3890 (18)C9—H90.9500
N3—H3N0.8800C13—C141.379 (2)
N4—C121.327 (2)C14—C151.392 (2)
N4—C131.3449 (19)C14—H140.9500
N5—C151.3303 (19)C16—H16A0.9800
N5—C121.333 (2)C16—H16B0.9800
C1—C21.480 (3)C16—H16C0.9800
C1—C31.495 (2)C17—H17A0.9800
C1—H1A0.9900C17—H17B0.9800
C1—H1B0.9900C17—H17C0.9800
O2—S1—O3120.02 (7)C7—C6—C5122.31 (17)
O2—S1—N1104.90 (7)C7—C6—H6118.8
O3—S1—N1111.04 (7)C5—C6—H6118.8
O2—S1—N2110.02 (7)C6—C7—C8118.96 (17)
O3—S1—N2102.97 (7)C6—C7—H7120.5
N1—S1—N2107.42 (7)C8—C7—H7120.5
C13—O5—C16116.90 (13)C7—C8—C9120.99 (17)
C15—O6—C17116.82 (13)C7—C8—H8119.5
C10—N1—S1127.72 (10)C9—C8—H8119.5
C10—N1—H1N116.1C8—C9—C10120.18 (16)
S1—N1—H1N116.1C8—C9—H9119.9
C11—N2—S1123.13 (10)C10—C9—H9119.9
C11—N2—H2N118.4C9—C10—N1122.06 (14)
S1—N2—H2N118.4C9—C10—C5119.97 (14)
C11—N3—C12130.81 (13)N1—C10—C5117.98 (13)
C11—N3—H3N114.6O4—C11—N3121.65 (14)
C12—N3—H3N114.6O4—C11—N2123.54 (14)
C12—N4—C13115.60 (13)N3—C11—N2114.81 (12)
C15—N5—C12114.47 (13)N4—C12—N5127.86 (14)
C2—C1—C360.76 (12)N4—C12—N3118.65 (14)
C2—C1—H1A117.7N5—C12—N3113.49 (13)
C3—C1—H1A117.7O5—C13—N4112.08 (13)
C2—C1—H1B117.7O5—C13—C14125.27 (14)
C3—C1—H1B117.7N4—C13—C14122.65 (14)
H1A—C1—H1B114.8C13—C14—C15115.36 (14)
C1—C2—C360.10 (12)C13—C14—H14122.3
C1—C2—H2A117.8C15—C14—H14122.3
C3—C2—H2A117.8N5—C15—O6119.06 (15)
C1—C2—H2B117.8N5—C15—C14124.04 (15)
C3—C2—H2B117.8O6—C15—C14116.89 (14)
H2A—C2—H2B114.9O5—C16—H16A109.5
C4—C3—C1119.02 (16)O5—C16—H16B109.5
C4—C3—C2116.34 (14)H16A—C16—H16B109.5
C1—C3—C259.14 (12)O5—C16—H16C109.5
C4—C3—H3116.6H16A—C16—H16C109.5
C1—C3—H3116.6H16B—C16—H16C109.5
C2—C3—H3116.6O6—C17—H17A109.5
O1—C4—C3119.04 (15)O6—C17—H17B109.5
O1—C4—C5121.68 (14)H17A—C17—H17B109.5
C3—C4—C5119.26 (15)O6—C17—H17C109.5
C6—C5—C10117.59 (15)H17A—C17—H17C109.5
C6—C5—C4120.40 (15)H17B—C17—H17C109.5
C10—C5—C4122.01 (14)
O2—S1—N1—C10176.89 (13)C4—C5—C10—C9−179.69 (15)
O3—S1—N1—C10−52.05 (15)C6—C5—C10—N1−179.72 (15)
N2—S1—N1—C1059.84 (15)C4—C5—C10—N10.3 (2)
O2—S1—N2—C11−47.34 (14)C12—N3—C11—O4−177.90 (15)
O3—S1—N2—C11−176.41 (12)C12—N3—C11—N21.5 (2)
N1—S1—N2—C1166.31 (13)S1—N2—C11—O4−10.3 (2)
C2—C1—C3—C4−105.05 (18)S1—N2—C11—N3170.31 (11)
C1—C2—C3—C4109.56 (18)C13—N4—C12—N5−0.8 (2)
C1—C3—C4—O14.1 (2)C13—N4—C12—N3178.68 (14)
C2—C3—C4—O1−63.6 (2)C15—N5—C12—N41.3 (2)
C1—C3—C4—C5−177.36 (15)C15—N5—C12—N3−178.23 (14)
C2—C3—C4—C5114.96 (19)C11—N3—C12—N4−2.0 (2)
O1—C4—C5—C6177.40 (17)C11—N3—C12—N5177.54 (15)
C3—C4—C5—C6−1.1 (2)C16—O5—C13—N4−179.99 (16)
O1—C4—C5—C10−2.6 (3)C16—O5—C13—C14−0.3 (2)
C3—C4—C5—C10178.88 (14)C12—N4—C13—O5179.06 (13)
C10—C5—C6—C7−1.0 (3)C12—N4—C13—C14−0.6 (2)
C4—C5—C6—C7179.00 (18)O5—C13—C14—C15−178.31 (15)
C5—C6—C7—C80.7 (3)N4—C13—C14—C151.3 (2)
C6—C7—C8—C90.4 (3)C12—N5—C15—O6178.96 (14)
C7—C8—C9—C10−1.0 (3)C12—N5—C15—C14−0.4 (2)
C8—C9—C10—N1−179.31 (16)C17—O6—C15—N51.8 (2)
C8—C9—C10—C50.7 (3)C17—O6—C15—C14−178.78 (15)
S1—N1—C10—C910.3 (2)C13—C14—C15—N5−0.8 (2)
S1—N1—C10—C5−169.74 (12)C13—C14—C15—O6179.85 (15)
C6—C5—C10—C90.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.881.862.5736 (18)137
N2—H2N···N40.881.922.6158 (18)135
C9—H9···O30.952.453.088 (2)124
N3—H3N···O2i0.882.082.9391 (17)165
C2—H2B···O2ii0.992.513.483 (2)169
C3—H3···O4iii1.002.513.286 (2)135
C8—H8···O3iv0.952.503.307 (2)142
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+3/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.881.862.5736 (18)137
N2—H2N···N40.881.922.6158 (18)135
C9—H9···O30.952.453.088 (2)124
N3—H3N···O2i0.882.082.9391 (17)165
C2—H2B···O2ii0.992.513.483 (2)169
C3—H3···O4iii1.002.513.286 (2)135
C8—H8···O3iv0.952.503.307 (2)142
Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+3/2, y−1/2, −z+1/2.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

References

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 First citationSarıgül, T. & İnam, R. (2009). Electrochim. Acta, 54, 5376–5380.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationXia, J., Li, F., Yin, L., Yu, D. & Wu, D. (2008). Acta Cryst. E64, o632.  CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o631-o632
https://doi.org/10.1107/S2056989015014115
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