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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-[(4-Methyl­benzene­sulfonamido)­meth­yl]cyclo­hexa­necarb­­oxy­lic acid

aDepartment of Chemistry, University of Gujrat, H.H. Campus, Gujrat 50700, Pakistan, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and cDepartment of Chemistry, Government College University, Lahore 54000, Pakistan
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 24 May 2011; accepted 26 May 2011; online 4 June 2011)

The title compound, C15H21NO4S, crystallized with two independent mol­ecules in the asymmetric unit in which the dihedral angles between the mean planes of the benzene and cyclo­hexane rings are 78.3 (2) and 67.6 (2)°. The substituents of the cyclo­hexyl rings are in equatorial orientations. In the crystal, both mol­ecules form R22(6) carb­oxy­lic acid inversion dimers via pairs of O—H⋯O hydrogen bonds. Further N—H⋯O and C—H⋯O inter­actions generate a three-dimensional network.

Related literature

For background to tranexamic acid, see: Boylan et al. (1996[Boylan, J. F., Klinck, J. R., Sandier, A. N., Arellano, R., Greig, P. D., Nierenberg, H., Roger, S. L. & Glynnix, M. F. (1996). Anesthesiology, 85, 1043-1048.]); Nilsson (1980[Nilsson, I. M. (1980). J. Clin. Pathol. Suppl. 14, 41-47.]); Khan et al. (2002[Khan, M. F., Khan, M. F., Ashfaq, M. & Khan, G. M. (2002). Pak. J. Pharm. Sci. 15, 55-62.]); Shah et al. (2010[Shah, F. A., Ali, S. & Shahzadi, S. (2010). J. Iran. Chem. Soc. 7, 59-68.]); Shahzadi et al. (2007[Shahzadi, S., Ali, S., Parvez, M., Badshah, A., Ahmed, E. & Malik, A. (2007). Russ. J. Inorg. Chem. 52, 386-393.]); Svahn et al. (1986[Svahn, C. M., Merenyi, F., Karlson, L., Widlund, L. & Gralls, M. (1986). J. Med. Chem. 29, 448-453.]); Vávrová et al. (2005[Vávrová, K., Hrabálek, A., Doležal, P., Holas, T. & Klimentová, J. (2005). J. Control. Release, 104, 41-49.]).

[Scheme 1]

Experimental

Crystal data
  • C15H21NO4S

  • Mr = 311.40

  • Triclinic, [P \overline 1]

  • a = 6.0655 (5) Å

  • b = 10.3999 (9) Å

  • c = 26.468 (2) Å

  • α = 98.947 (3)°

  • β = 90.001 (4)°

  • γ = 104.880 (3)°

  • V = 1592.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 296 K

  • 0.24 × 0.18 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 18232 measured reflections

  • 7641 independent reflections

  • 3536 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.076

  • wR(F2) = 0.227

  • S = 1.02

  • 7641 reflections

  • 394 parameters

  • 5 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4O⋯O3i 0.84 (4) 1.81 (4) 2.638 (6) 171 (4)
O7—H7O⋯O8ii 0.81 (4) 1.87 (4) 2.664 (5) 166 (5)
N1—H1N⋯O6iii 0.86 (3) 2.15 (3) 3.001 (4) 171 (4)
N2—H2N⋯O2 0.84 (3) 2.09 (4) 2.924 (4) 171 (4)
C10—H10B⋯O6iii 0.97 2.57 3.446 (6) 151
C19—H19⋯O2 0.93 2.59 3.490 (5) 164
Symmetry codes: (i) -x+3, -y, -z+1; (ii) -x+3, -y+2, -z+2; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

Tranexamic acid, is a synthetic amino acid that is used commonly for curing abnormal bleeding in a variety of diseases (Boylan et al., 1996; Nilsson, 1980). Number of Scientists derivatized this drug, evaluated their activities and found most of them superior to the parent drug (Svahn et al., 1986; Khan et al., 2002; Vávrová et al., 2005; Shahzadi et al., 2007; Shah et al., 2010).

As seen in Fig. 1, the title compound (I) crystalizes in the triclinic space group P-1 with two independent molecules in the asymmetric unit. The dihedral angle is 64.7 (2) ° between the benzene rings (C2–C7 and C17–C22) of two independent molecules in the asymmetric unit. The cyclohexane rings (C9–C14 and C24–C29) of two independent molecules have a chair configuration [the puckering parameters are QT = 0.561 (5) Å, θ = 174.4 (5) °, ϕ = 353 (6) ° and QT = 0.563 (5) Å, θ = 0.8 (5) °, ϕ = 139 (29) °, respectively].

In the crystal structure, intermolecular N—H···O, O—H···O and C—H···O interactions help to stabilize the crystal structure (Table 1, Fig. 2).

Related literature top

For background to tranexamic acid, see: Boylan et al. (1996); Nilsson (1980); Khan et al. (2002); Shah et al. (2010); Shahzadi et al. (2007); Svahn et al. (1986); Vávrová et al. (2005).

Experimental top

4-toluenesulfonyl chloride (1.21 g, 6.36 mmol) was added to the solution of tranexamic acid (1.0 g, 6.36 mmol) in distilled water (10 ml). The reaction mixture was stirred at room temperature at pH 8–9, which was adjusted by 1 M sodium carbonate solution. After completion of the reaction which was observed by the consumption of 4-toluenesulfonyl chloride, the pH was adjusted at 2–3 using 1 N HCl solution, which results the formation of precipiates, which were filtered off and dried. The product was recrystallized using methanol to yield colourless plates of (I).

Refinement top

The N and O-bound H atoms were located in a difference Fourier map and their positional parameters were restrained [N1—H1N = 0.86 (3), N2—H2N = 0.84 (3), O4—H4O = 0.84 (4) and O7—H7O = 0.81 (4) Å]. Their displacement parameters were refined using a riding model, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O). The remaining H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93 - 0.98 Å, and Uiso = 1.2Ueq(C) for CH and CH2 groups and Uiso = 1.5Ueq(C) for CH3 group.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the two independent molecules in the asymmetric unit with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing and hydrogen bonding of (I), viewed down a axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
4-[(4-Methylbenzenesulfonamido)methyl]cyclohexanecarboxylic acid top
Crystal data top
C15H21NO4SZ = 4
Mr = 311.40F(000) = 664
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0655 (5) ÅCell parameters from 2057 reflections
b = 10.3999 (9) Åθ = 2.8–21.5°
c = 26.468 (2) ŵ = 0.22 mm1
α = 98.947 (3)°T = 296 K
β = 90.001 (4)°Plate, colourless
γ = 104.880 (3)°0.24 × 0.18 × 0.07 mm
V = 1592.6 (2) Å3
Data collection top
Bruker APEXII CCD
diffractometer
3536 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.059
Graphite monochromatorθmax = 28.3°, θmin = 2.3°
ϕ and ω scansh = 58
18232 measured reflectionsk = 1313
7641 independent reflectionsl = 3335
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)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1014P)2]
where P = (Fo2 + 2Fc2)/3
7641 reflections(Δ/σ)max = 0.001
394 parametersΔρmax = 0.53 e Å3
5 restraintsΔρmin = 0.35 e Å3
Crystal data top
C15H21NO4Sγ = 104.880 (3)°
Mr = 311.40V = 1592.6 (2) Å3
Triclinic, P1Z = 4
a = 6.0655 (5) ÅMo Kα radiation
b = 10.3999 (9) ŵ = 0.22 mm1
c = 26.468 (2) ÅT = 296 K
α = 98.947 (3)°0.24 × 0.18 × 0.07 mm
β = 90.001 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
3536 reflections with I > 2σ(I)
18232 measured reflectionsRint = 0.059
7641 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0765 restraints
wR(F2) = 0.227H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.53 e Å3
7641 reflectionsΔρmin = 0.35 e Å3
394 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
S10.59294 (16)0.36920 (10)0.78560 (4)0.0462 (3)
O10.4029 (4)0.2571 (3)0.78800 (10)0.0609 (10)
O20.5563 (5)0.4991 (3)0.78533 (10)0.0647 (11)
O31.2671 (7)0.0636 (4)0.53183 (13)0.1013 (17)
O41.4863 (7)0.1415 (4)0.54321 (14)0.1083 (17)
N10.7227 (5)0.3365 (3)0.73371 (11)0.0450 (11)
C11.2352 (11)0.4191 (6)0.96605 (19)0.114 (3)
C21.0735 (9)0.4061 (5)0.92107 (17)0.0733 (19)
C31.1413 (8)0.4766 (6)0.88168 (19)0.093 (2)
C40.9963 (8)0.4656 (5)0.84050 (17)0.0814 (19)
C50.7805 (6)0.3824 (4)0.83802 (13)0.0442 (12)
C60.7115 (8)0.3108 (4)0.87682 (15)0.0656 (17)
C70.8597 (10)0.3241 (5)0.91804 (17)0.082 (2)
C80.7808 (7)0.2069 (4)0.72344 (14)0.0562 (16)
C90.8747 (8)0.1807 (4)0.67113 (16)0.0592 (17)
C101.0961 (9)0.2721 (5)0.6634 (2)0.092 (2)
C111.1912 (10)0.2368 (4)0.61059 (19)0.093 (2)
C121.2054 (9)0.0906 (4)0.60319 (17)0.0717 (19)
C130.9806 (9)0.0001 (5)0.60706 (19)0.084 (2)
C140.8840 (10)0.0355 (4)0.65955 (18)0.086 (2)
C151.3243 (9)0.0523 (5)0.55579 (17)0.0653 (17)
S20.25305 (15)0.71011 (9)0.71862 (3)0.0417 (3)
O50.1844 (5)0.8290 (3)0.71441 (10)0.0600 (10)
O60.0813 (4)0.5889 (3)0.72280 (9)0.0562 (9)
O71.3989 (6)1.0912 (4)0.95942 (13)0.0918 (17)
O81.2587 (6)0.8845 (3)0.97377 (12)0.0874 (12)
N20.4188 (5)0.7396 (3)0.76897 (10)0.0416 (10)
C160.7982 (10)0.5973 (6)0.53281 (18)0.110 (3)
C170.6599 (8)0.6246 (5)0.57895 (16)0.0673 (17)
C180.6913 (8)0.5789 (5)0.62363 (18)0.0771 (19)
C190.5698 (8)0.6030 (5)0.66593 (16)0.0675 (17)
C200.4129 (6)0.6759 (4)0.66451 (13)0.0429 (11)
C210.3779 (8)0.7221 (4)0.61988 (15)0.0649 (17)
C220.4988 (10)0.6941 (5)0.57743 (17)0.084 (2)
C230.6137 (6)0.8615 (4)0.77586 (13)0.0464 (12)
C240.7819 (6)0.8593 (4)0.81700 (13)0.0487 (12)
C250.6862 (7)0.8384 (5)0.86771 (15)0.0705 (18)
C260.8735 (7)0.8386 (5)0.90713 (15)0.0674 (16)
C271.0635 (7)0.9679 (4)0.91159 (15)0.0641 (17)
C281.1607 (7)0.9884 (5)0.86120 (15)0.0728 (19)
C290.9747 (7)0.9873 (4)0.82208 (14)0.0597 (14)
C301.2480 (7)0.9766 (5)0.95100 (15)0.0604 (16)
H1A1.276800.510800.983200.1720*
H1B1.369800.393600.954100.1720*
H1C1.161700.361100.989400.1720*
H1N0.831 (6)0.408 (3)0.7338 (16)0.0790*
H31.288300.532900.882900.1110*
H41.045000.514800.814300.0980*
H4O1.555 (6)0.119 (3)0.5172 (13)0.0980*
H60.565500.253300.875500.0790*
H70.811100.275300.944400.0990*
H8A0.645200.135200.726300.0670*
H8B0.893000.204900.749200.0670*
H90.764900.192700.646300.0710*
H10A1.205000.269300.689800.1100*
H10B1.079900.363400.667200.1100*
H11A1.092100.248700.583900.1120*
H11B1.341700.296300.608400.1120*
H121.299500.083100.632100.0860*
H13A0.992500.092400.602600.1010*
H13B0.878000.007200.580200.1010*
H14A0.731200.022500.660600.1030*
H14B0.978000.017700.685900.1030*
H2N0.442 (7)0.666 (3)0.7742 (15)0.0720*
H7O1.502 (6)1.085 (5)0.9778 (16)0.0900*
H16A0.710200.592600.502100.1650*
H16B0.836400.513200.532700.1650*
H16C0.935700.668700.534300.1650*
H180.798900.529800.625200.0930*
H190.593800.569800.695500.0810*
H210.272200.772500.618500.0780*
H220.469800.723100.547200.1010*
H23A0.556800.940800.784600.0560*
H23B0.690500.867700.743800.0560*
H240.848500.784000.805200.0580*
H25A0.571000.753000.864000.0840*
H25B0.613300.909400.880100.0840*
H26A0.807600.830200.940200.0810*
H26B0.935700.761900.896700.0810*
H270.994401.042500.922900.0770*
H28A1.234100.917400.849100.0880*
H28B1.275601.073900.864900.0880*
H29A0.913601.064500.832400.0720*
H29B1.041300.995500.789000.0720*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0430 (5)0.0572 (6)0.0446 (6)0.0194 (5)0.0095 (4)0.0158 (4)
O10.0422 (15)0.080 (2)0.0572 (17)0.0050 (14)0.0078 (13)0.0194 (14)
O20.079 (2)0.0739 (19)0.0602 (18)0.0466 (17)0.0198 (15)0.0231 (15)
O30.116 (3)0.082 (3)0.093 (3)0.018 (2)0.046 (2)0.012 (2)
O40.123 (3)0.091 (3)0.099 (3)0.019 (2)0.064 (3)0.006 (2)
N10.0477 (19)0.051 (2)0.0425 (17)0.0195 (15)0.0098 (15)0.0149 (15)
C10.113 (5)0.165 (6)0.072 (4)0.063 (4)0.031 (3)0.006 (3)
C20.074 (3)0.095 (4)0.054 (3)0.039 (3)0.010 (2)0.007 (3)
C30.051 (3)0.151 (5)0.067 (3)0.010 (3)0.007 (2)0.018 (3)
C40.053 (3)0.123 (4)0.064 (3)0.002 (3)0.004 (2)0.038 (3)
C50.045 (2)0.049 (2)0.041 (2)0.0157 (18)0.0083 (17)0.0083 (17)
C60.071 (3)0.064 (3)0.056 (3)0.001 (2)0.000 (2)0.023 (2)
C70.105 (4)0.089 (4)0.053 (3)0.018 (3)0.006 (3)0.025 (3)
C80.073 (3)0.057 (3)0.047 (2)0.025 (2)0.012 (2)0.0202 (19)
C90.068 (3)0.058 (3)0.060 (3)0.027 (2)0.023 (2)0.017 (2)
C100.071 (3)0.086 (4)0.105 (4)0.014 (3)0.026 (3)0.016 (3)
C110.111 (4)0.061 (3)0.098 (4)0.014 (3)0.064 (4)0.004 (3)
C120.082 (4)0.073 (3)0.065 (3)0.033 (3)0.022 (3)0.004 (2)
C130.090 (4)0.067 (3)0.093 (4)0.027 (3)0.030 (3)0.002 (3)
C140.119 (5)0.059 (3)0.086 (4)0.032 (3)0.050 (3)0.017 (3)
C150.075 (3)0.069 (3)0.058 (3)0.029 (3)0.020 (3)0.011 (3)
S20.0352 (5)0.0511 (6)0.0402 (5)0.0129 (4)0.0003 (4)0.0085 (4)
O50.0653 (18)0.0715 (19)0.0554 (17)0.0386 (15)0.0008 (14)0.0119 (14)
O60.0385 (14)0.0642 (18)0.0570 (16)0.0050 (13)0.0009 (12)0.0134 (13)
O70.080 (3)0.092 (3)0.093 (3)0.000 (2)0.045 (2)0.0209 (19)
O80.077 (2)0.094 (2)0.085 (2)0.0004 (19)0.0317 (18)0.0339 (19)
N20.0432 (17)0.0455 (19)0.0356 (16)0.0095 (15)0.0033 (13)0.0088 (14)
C160.086 (4)0.163 (6)0.064 (3)0.018 (4)0.027 (3)0.007 (3)
C170.053 (3)0.086 (3)0.050 (3)0.003 (2)0.005 (2)0.003 (2)
C180.062 (3)0.105 (4)0.071 (3)0.038 (3)0.010 (3)0.007 (3)
C190.072 (3)0.094 (3)0.053 (3)0.046 (3)0.017 (2)0.021 (2)
C200.0376 (19)0.048 (2)0.040 (2)0.0055 (17)0.0024 (16)0.0070 (17)
C210.077 (3)0.080 (3)0.049 (3)0.035 (3)0.007 (2)0.020 (2)
C220.102 (4)0.114 (4)0.044 (3)0.036 (3)0.012 (3)0.022 (3)
C230.047 (2)0.053 (2)0.037 (2)0.0067 (18)0.0012 (16)0.0109 (17)
C240.043 (2)0.056 (2)0.045 (2)0.0076 (18)0.0065 (17)0.0111 (18)
C250.047 (2)0.103 (4)0.054 (3)0.003 (2)0.000 (2)0.018 (2)
C260.054 (3)0.094 (3)0.046 (2)0.004 (2)0.009 (2)0.026 (2)
C270.057 (3)0.076 (3)0.051 (3)0.003 (2)0.015 (2)0.009 (2)
C280.052 (3)0.098 (4)0.057 (3)0.007 (2)0.003 (2)0.023 (2)
C290.048 (2)0.072 (3)0.052 (2)0.003 (2)0.0085 (19)0.020 (2)
C300.054 (3)0.073 (3)0.046 (2)0.005 (2)0.005 (2)0.004 (2)
Geometric parameters (Å, º) top
S1—O11.423 (3)C10—H10B0.9700
S1—O21.425 (3)C10—H10A0.9700
S1—N11.617 (3)C11—H11A0.9700
S1—C51.760 (4)C11—H11B0.9700
S2—N21.611 (3)C12—H120.9800
S2—O51.422 (3)C13—H13A0.9700
S2—O61.434 (3)C13—H13B0.9700
S2—C201.771 (4)C14—H14B0.9700
O3—C151.234 (6)C14—H14A0.9700
O4—C151.251 (7)C16—C171.513 (7)
O4—H4O0.84 (4)C17—C181.372 (7)
O7—C301.290 (6)C17—C221.360 (8)
O8—C301.223 (6)C18—C191.366 (7)
O7—H7O0.81 (4)C19—C201.364 (6)
N1—C81.465 (5)C20—C211.379 (5)
N1—H1N0.86 (3)C21—C221.376 (7)
N2—C231.482 (5)C23—C241.499 (5)
N2—H2N0.84 (3)C24—C291.517 (6)
C1—C21.510 (8)C24—C251.487 (5)
C2—C31.370 (7)C25—C261.542 (6)
C2—C71.351 (8)C26—C271.518 (6)
C3—C41.373 (7)C27—C281.482 (6)
C4—C51.366 (6)C27—C301.506 (6)
C5—C61.365 (5)C28—C291.528 (6)
C6—C71.381 (7)C16—H16A0.9600
C8—C91.509 (6)C16—H16B0.9600
C9—C141.509 (6)C16—H16C0.9600
C9—C101.468 (7)C18—H180.9300
C10—C111.540 (7)C19—H190.9300
C11—C121.527 (6)C21—H210.9300
C12—C151.498 (7)C22—H220.9300
C12—C131.459 (7)C23—H23A0.9700
C13—C141.537 (7)C23—H23B0.9700
C1—H1A0.9600C24—H240.9800
C1—H1B0.9600C25—H25A0.9700
C1—H1C0.9600C25—H25B0.9700
C3—H30.9300C26—H26A0.9700
C4—H40.9300C26—H26B0.9700
C6—H60.9300C27—H270.9800
C7—H70.9300C28—H28A0.9700
C8—H8B0.9700C28—H28B0.9700
C8—H8A0.9700C29—H29A0.9700
C9—H90.9800C29—H29B0.9700
O1—S1—O2119.56 (18)C14—C13—H13A110.00
O1—S1—N1107.94 (16)C12—C13—H13A110.00
O1—S1—C5107.47 (18)C12—C13—H13B110.00
O2—S1—N1105.84 (17)C14—C13—H13B110.00
O2—S1—C5107.52 (18)H13A—C13—H13B108.00
N1—S1—C5108.07 (17)C13—C14—H14B109.00
N2—S2—C20108.08 (17)H14A—C14—H14B108.00
O5—S2—N2108.46 (16)C9—C14—H14B109.00
O5—S2—C20107.58 (18)C13—C14—H14A109.00
O5—S2—O6118.87 (18)C9—C14—H14A109.00
O6—S2—C20107.80 (17)C16—C17—C18121.1 (5)
O6—S2—N2105.65 (15)C16—C17—C22121.2 (4)
C15—O4—H4O117 (2)C18—C17—C22117.7 (4)
C30—O7—H7O109 (4)C17—C18—C19122.2 (5)
S1—N1—C8118.0 (2)C18—C19—C20119.7 (4)
S1—N1—H1N104 (3)S2—C20—C19121.1 (3)
C8—N1—H1N118 (2)S2—C20—C21119.9 (3)
S2—N2—C23118.2 (2)C19—C20—C21119.0 (4)
S2—N2—H2N108 (3)C20—C21—C22120.3 (4)
C23—N2—H2N119 (3)C17—C22—C21121.1 (4)
C3—C2—C7118.0 (5)N2—C23—C24112.1 (3)
C1—C2—C3120.6 (5)C25—C24—C29110.7 (3)
C1—C2—C7121.4 (5)C23—C24—C29109.0 (3)
C2—C3—C4121.2 (5)C23—C24—C25115.8 (3)
C3—C4—C5120.1 (4)C24—C25—C26111.5 (4)
S1—C5—C6120.5 (3)C25—C26—C27110.6 (4)
C4—C5—C6119.3 (4)C26—C27—C28111.3 (3)
S1—C5—C4120.3 (3)C26—C27—C30113.2 (4)
C5—C6—C7119.7 (4)C28—C27—C30111.1 (4)
C2—C7—C6121.8 (4)C27—C28—C29110.9 (4)
N1—C8—C9113.0 (3)C24—C29—C28112.0 (3)
C10—C9—C14111.0 (4)O7—C30—O8121.4 (4)
C8—C9—C14109.4 (4)O7—C30—C27114.5 (4)
C8—C9—C10115.1 (4)O8—C30—C27124.2 (4)
C9—C10—C11113.3 (4)C17—C16—H16A110.00
C10—C11—C12109.2 (4)C17—C16—H16B110.00
C13—C12—C15113.7 (4)C17—C16—H16C109.00
C11—C12—C15113.0 (4)H16A—C16—H16B109.00
C11—C12—C13110.5 (5)H16A—C16—H16C109.00
C12—C13—C14110.3 (4)H16B—C16—H16C109.00
C9—C14—C13113.0 (4)C17—C18—H18119.00
O4—C15—C12116.8 (4)C19—C18—H18119.00
O3—C15—O4122.6 (5)C18—C19—H19120.00
O3—C15—C12120.5 (5)C20—C19—H19120.00
C2—C1—H1C109.00C20—C21—H21120.00
H1A—C1—H1B110.00C22—C21—H21120.00
H1A—C1—H1C110.00C17—C22—H22119.00
H1B—C1—H1C109.00C21—C22—H22119.00
C2—C1—H1B109.00N2—C23—H23A109.00
C2—C1—H1A109.00N2—C23—H23B109.00
C4—C3—H3119.00C24—C23—H23A109.00
C2—C3—H3119.00C24—C23—H23B109.00
C3—C4—H4120.00H23A—C23—H23B108.00
C5—C4—H4120.00C23—C24—H24107.00
C7—C6—H6120.00C25—C24—H24107.00
C5—C6—H6120.00C29—C24—H24107.00
C2—C7—H7119.00C24—C25—H25A109.00
C6—C7—H7119.00C24—C25—H25B109.00
H8A—C8—H8B108.00C26—C25—H25A109.00
N1—C8—H8B109.00C26—C25—H25B109.00
C9—C8—H8B109.00H25A—C25—H25B108.00
N1—C8—H8A109.00C25—C26—H26A109.00
C9—C8—H8A109.00C25—C26—H26B110.00
C10—C9—H9107.00C27—C26—H26A110.00
C14—C9—H9107.00C27—C26—H26B110.00
C8—C9—H9107.00H26A—C26—H26B108.00
C9—C10—H10A109.00C26—C27—H27107.00
C9—C10—H10B109.00C28—C27—H27107.00
C11—C10—H10A109.00C30—C27—H27107.00
C11—C10—H10B109.00C27—C28—H28A109.00
H10A—C10—H10B108.00C27—C28—H28B109.00
C10—C11—H11B110.00C29—C28—H28A109.00
C12—C11—H11B110.00C29—C28—H28B110.00
C12—C11—H11A110.00H28A—C28—H28B108.00
C10—C11—H11A110.00C24—C29—H29A109.00
H11A—C11—H11B108.00C24—C29—H29B109.00
C13—C12—H12106.00C28—C29—H29A109.00
C15—C12—H12106.00C28—C29—H29B109.00
C11—C12—H12106.00H29A—C29—H29B108.00
O1—S1—N1—C850.3 (3)C9—C10—C11—C1255.7 (6)
O2—S1—N1—C8179.4 (3)C10—C11—C12—C1358.8 (5)
C5—S1—N1—C865.7 (3)C10—C11—C12—C15172.5 (4)
O1—S1—C5—C4168.2 (3)C11—C12—C15—O3147.3 (5)
O1—S1—C5—C612.5 (4)C11—C12—C15—O435.0 (7)
O2—S1—C5—C461.9 (4)C13—C12—C15—O4162.0 (5)
O2—S1—C5—C6117.5 (4)C15—C12—C13—C14172.9 (4)
N1—S1—C5—C451.9 (4)C13—C12—C15—O320.3 (7)
N1—S1—C5—C6128.7 (3)C11—C12—C13—C1458.8 (5)
O5—S2—C20—C2125.3 (4)C12—C13—C14—C955.4 (6)
O6—S2—C20—C1975.4 (4)C16—C17—C18—C19179.5 (5)
O6—S2—C20—C21104.0 (4)C22—C17—C18—C191.1 (8)
N2—S2—C20—C1938.4 (4)C16—C17—C22—C21178.1 (5)
N2—S2—C20—C21142.3 (3)C18—C17—C22—C212.5 (8)
O5—S2—N2—C2350.6 (3)C17—C18—C19—C200.7 (8)
O6—S2—N2—C23179.1 (3)C18—C19—C20—S2179.7 (4)
C20—S2—N2—C2365.7 (3)C18—C19—C20—C211.0 (7)
O5—S2—C20—C19155.3 (4)S2—C20—C21—C22179.0 (4)
S1—N1—C8—C9172.9 (3)C19—C20—C21—C220.4 (7)
S2—N2—C23—C24166.7 (2)C20—C21—C22—C172.2 (7)
C1—C2—C3—C4179.9 (5)N2—C23—C24—C2554.0 (5)
C7—C2—C3—C40.6 (8)N2—C23—C24—C29179.6 (3)
C3—C2—C7—C60.2 (8)C23—C24—C25—C26179.7 (4)
C1—C2—C7—C6179.4 (5)C29—C24—C25—C2655.0 (5)
C2—C3—C4—C50.5 (8)C23—C24—C29—C28176.6 (3)
C3—C4—C5—S1179.4 (4)C25—C24—C29—C2855.0 (4)
C3—C4—C5—C60.0 (7)C24—C25—C26—C2755.8 (5)
S1—C5—C6—C7178.9 (4)C25—C26—C27—C2856.1 (5)
C4—C5—C6—C70.4 (7)C25—C26—C27—C30177.9 (3)
C5—C6—C7—C20.4 (8)C26—C27—C28—C2956.0 (5)
N1—C8—C9—C1065.8 (5)C30—C27—C28—C29176.9 (4)
N1—C8—C9—C14168.5 (4)C26—C27—C30—O7173.0 (4)
C14—C9—C10—C1152.0 (5)C26—C27—C30—O87.0 (6)
C8—C9—C14—C13179.3 (4)C28—C27—C30—O760.9 (5)
C8—C9—C10—C11176.9 (4)C28—C27—C30—O8119.1 (5)
C10—C9—C14—C1351.3 (6)C27—C28—C29—C2455.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.84 (4)1.81 (4)2.638 (6)171 (4)
O7—H7O···O8ii0.81 (4)1.87 (4)2.664 (5)166 (5)
N1—H1N···O6iii0.86 (3)2.15 (3)3.001 (4)171 (4)
N2—H2N···O20.84 (3)2.09 (4)2.924 (4)171 (4)
C10—H10B···O6iii0.972.573.446 (6)151
C19—H19···O20.932.593.490 (5)164
Symmetry codes: (i) x+3, y, z+1; (ii) x+3, y+2, z+2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H21NO4S
Mr311.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)6.0655 (5), 10.3999 (9), 26.468 (2)
α, β, γ (°)98.947 (3), 90.001 (4), 104.880 (3)
V3)1592.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.24 × 0.18 × 0.07
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18232, 7641, 3536
Rint0.059
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.227, 1.02
No. of reflections7641
No. of parameters394
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.53, 0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O3i0.84 (4)1.81 (4)2.638 (6)171 (4)
O7—H7O···O8ii0.81 (4)1.87 (4)2.664 (5)166 (5)
N1—H1N···O6iii0.86 (3)2.15 (3)3.001 (4)171 (4)
N2—H2N···O20.84 (3)2.09 (4)2.924 (4)171 (4)
C10—H10B···O6iii0.972.573.446 (6)151
C19—H19···O20.932.593.490 (5)164
Symmetry codes: (i) x+3, y, z+1; (ii) x+3, y+2, z+2; (iii) x+1, y, z.
 

Footnotes

Additional correspondence author, e-mail: iukhan.gcu@gmail.com.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer. MA, SI and GM are grateful to the Vice Chancellor of the University of Gujrat, Professor Dr M. Nizamuddin, for creating a healthy research environment in the campus.

References

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