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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2248-o2249

4-[(4-Meth­­oxy­benzene­sulfonamido)­meth­yl]cyclo­hexane-1-carb­­oxy­lic 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 21 July 2011; accepted 29 July 2011; online 6 August 2011)

In the title compound, C15H21NO5S, two crystallographically independent mol­ecules are linked into a dimer by a pair of N—H⋯O hydrogen bonds, forming an R22(8) ring motif. In the crystal, mol­ecules are further linked by inter­molecular O—H⋯O hydrogen bonds into a two-dimensional network parallel to (012). Additional stabilization is provided by weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For background to tranexamic acid (trans-4-(amino­meth­yl)cyclo­hexa­necarb­oxy­lic 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.]); Khan et al. (2002[Khan, M. F., Khan, M. F., Ashfaq, M. & Khan, G. M. (2002). Pak. J. Pharm. Sci. 15, 55-62.]); Nilsson (1980[Nilsson, I. M. (1980). J. Clin. Pathol. Suppl. 14, 41-47.]); 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.]); Vavrova et al. (2005[Vavrova, K., Hrabalek, A., Dolezal, P., Holas, T. & Klimentova, J. (2005). J. Control. Release, 104, 41-49.]). For a related structure, see: Ashfaq et al. (2011[Ashfaq, M., Iram, S., Akkurt, M., Khan, I. U., Mustafa, G. & Sharif, S. (2011). Acta Cryst. E67, o1563.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C15H21NO5S

  • Mr = 327.40

  • Triclinic, [P \overline 1]

  • a = 5.9119 (3) Å

  • b = 10.7223 (7) Å

  • c = 26.6453 (15) Å

  • α = 79.736 (3)°

  • β = 89.813 (3)°

  • γ = 75.518 (3)°

  • V = 1607.67 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 296 K

  • 0.25 × 0.19 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 25440 measured reflections

  • 5942 independent reflections

  • 3973 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.218

  • S = 1.03

  • 5942 reflections

  • 412 parameters

  • 5 restraints

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

  • Δρmax = 0.92 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O8i 0.83 (4) 2.14 (3) 2.961 (4) 173 (3)
N2—H2N⋯O3ii 0.85 (3) 2.18 (3) 3.024 (4) 172 (3)
O4—H4O⋯O5iii 0.83 (5) 1.84 (5) 2.660 (5) 166 (6)
O10—H10O⋯O9iv 0.82 (7) 1.89 (8) 2.631 (8) 151 (7)
C16—H16B⋯O6v 0.96 2.59 3.378 (7) 139
C25—H25A⋯O3ii 0.97 2.54 3.450 (6) 157
Symmetry codes: (i) x, y+1, z; (ii) x+1, y-1, z; (iii) -x+3, -y+1, -z+2; (iv) -x+3, -y+1, -z+1; (v) -x+3, -y, -z+2.

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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Tranexamic acid or trans-4-(aminomethyl)cyclohexanecarboxylic acid, is a synthetic amino acid used commonly for curing abnormal bleeding in a variety of diseases (Boylan et al., 1996; Nilsson, 1980). A number of scientists derivatized this drug, evaluated the activity and found most derivatives were superior to the parent drug (Svahn et al., 1986; Khan et al., 2002; Vavrova et al., 2005; Shahzadi et al., 2007; Shah et al., 2010). We have recently prepared a derivative of this drug and reported the crystal structure (Ashfaq et al., 2011).

Fig. 1 shows the two crystallographically independent molecules in the asymmetric unit of the title compound (I). The molecules form a dimer, in which a pair of N—H···O hydrogen bonds generate an intermolecular R22(8) ring (Bernstein, et al., 1995). The cyclohexane rings (C9–C14 and C24–C29) in each molecule adopt a chair configuration [the puckering parameters are QT = 0.547 (5) Å, θ = 180.0 (5) °, ϕ = 286 (35) ° and QT = 0.561 (6) Å, θ = 3.7 (5) °, ϕ = 161 (8) °, respectively] (Cremer & Pople, 1975). In the crystal, molecules are further linked by intermolecular O—H···O hydrogen bonds to form a two-dimensional network parallel to (012). Additional stabilization is provided by weak intermoleclar C—H···O hydrogen bonds (Fig. 2).

Related literature top

For background to tranexamic acid (trans-4-(aminomethyl)cyclohexanecarboxylic acid), see: Boylan et al. (1996); Khan et al. (2002); Nilsson (1980); Shah et al. (2010); Shahzadi et al. (2007); Svahn et al. (1986); Vavrova et al. (2005). For a related structure, see: Ashfaq et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

4-Methoxybenzene sulfonyl chloride (1.32 g, 6.36 mmol) was added to a 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 1M sodium carbonate solution. After completion of the reaction which was observed by the consumption of 4-methoxybenzene sulfonyl chloride, the pH was adjusted at 2–3 using 1 N HCl solution, which resulted in the formation of precipiates. these were filtered off and dried. The product was recrystallized using methanol.

Refinement top

The H atoms of the –NH and –OH groups were located in a difference Fourier map and their positional parameters were restrained [N1—H1N = 0.83 (4), N2—H2N = 0.85 (3), O4—H4O = 0.83 (5) and O10—H10O = 0.82 (7) Å]. Their displacement parameters were refined using a riding model, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O). The other H atoms were placed in ideal positions and refined as riding 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The two independent molecules in the asymmetric unit with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing and hydrogen bonding of viewed along the a axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
4-[(4-Methoxybenzenesulfonamido)methyl]cyclohexane-1-carboxylic acid top
Crystal data top
C15H21NO5SZ = 4
Mr = 327.40F(000) = 696
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9119 (3) ÅCell parameters from 4861 reflections
b = 10.7223 (7) Åθ = 2.8–24.1°
c = 26.6453 (15) ŵ = 0.22 mm1
α = 79.736 (3)°T = 296 K
β = 89.813 (3)°Block, colourless
γ = 75.518 (3)°0.25 × 0.19 × 0.14 mm
V = 1607.67 (16) Å3
Data collection top
Bruker APEXII CCD
diffractometer
3973 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.5°, θmin = 0.8°
ϕ and ω scansh = 77
25440 measured reflectionsk = 1212
5942 independent reflectionsl = 3231
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1117P)2 + 1.5531P]
where P = (Fo2 + 2Fc2)/3
5942 reflections(Δ/σ)max = 0.001
412 parametersΔρmax = 0.92 e Å3
5 restraintsΔρmin = 0.36 e Å3
Crystal data top
C15H21NO5Sγ = 75.518 (3)°
Mr = 327.40V = 1607.67 (16) Å3
Triclinic, P1Z = 4
a = 5.9119 (3) ÅMo Kα radiation
b = 10.7223 (7) ŵ = 0.22 mm1
c = 26.6453 (15) ÅT = 296 K
α = 79.736 (3)°0.25 × 0.19 × 0.14 mm
β = 89.813 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
3973 reflections with I > 2σ(I)
25440 measured reflectionsRint = 0.048
5942 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0705 restraints
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.92 e Å3
5942 reflectionsΔρmin = 0.36 e Å3
412 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
S10.24030 (15)0.81008 (9)0.71667 (3)0.0404 (3)
O10.8071 (6)0.9302 (4)0.54159 (12)0.0852 (16)
O20.1613 (5)0.6977 (3)0.71162 (10)0.0541 (10)
O30.0718 (4)0.9282 (3)0.72214 (10)0.0522 (9)
O41.4245 (6)0.4189 (3)0.95284 (13)0.0772 (12)
O51.2465 (6)0.6045 (3)0.97576 (13)0.0827 (12)
N10.4128 (5)0.7734 (3)0.76697 (11)0.0405 (10)
C10.8230 (11)0.8647 (6)0.49907 (19)0.091 (2)
C20.6699 (8)0.8966 (4)0.58007 (16)0.0593 (16)
C30.6843 (8)0.9522 (5)0.62271 (17)0.0662 (17)
C40.5527 (7)0.9266 (4)0.66397 (16)0.0592 (16)
C50.4061 (6)0.8452 (3)0.66319 (13)0.0402 (11)
C60.3904 (8)0.7915 (4)0.62065 (15)0.0570 (16)
C70.5216 (9)0.8176 (4)0.57891 (16)0.0655 (16)
C80.6083 (6)0.6550 (4)0.77250 (14)0.0446 (12)
C90.7785 (7)0.6474 (4)0.81491 (16)0.0543 (12)
C100.6831 (8)0.6655 (5)0.86445 (17)0.0713 (19)
C110.8758 (8)0.6601 (5)0.90438 (17)0.0722 (19)
C121.0675 (8)0.5335 (5)0.90841 (17)0.0661 (17)
C131.1619 (8)0.5154 (5)0.85893 (18)0.0789 (19)
C140.9709 (8)0.5220 (4)0.81929 (17)0.0649 (17)
C151.2557 (7)0.5231 (4)0.94865 (16)0.0536 (14)
S20.58540 (16)0.13448 (10)0.78880 (4)0.0452 (3)
O61.2525 (6)0.0555 (4)0.96080 (12)0.0810 (14)
O70.3919 (4)0.2420 (3)0.79281 (11)0.0585 (10)
O80.5465 (5)0.0094 (3)0.78645 (11)0.0614 (11)
O91.2935 (9)0.5689 (4)0.53819 (18)0.126 (2)
O101.4743 (11)0.3683 (4)0.5428 (2)0.141 (2)
N20.7154 (5)0.1743 (3)0.73693 (11)0.0445 (10)
C161.2095 (10)0.1349 (5)0.99941 (19)0.0815 (19)
C171.0888 (8)0.0813 (4)0.92229 (15)0.0560 (16)
C181.1491 (8)0.0089 (5)0.88368 (18)0.0702 (16)
C190.9954 (7)0.0252 (5)0.84341 (16)0.0650 (16)
C200.7813 (6)0.1140 (4)0.84073 (13)0.0416 (11)
C210.7221 (7)0.1857 (4)0.87863 (15)0.0564 (14)
C220.8754 (8)0.1698 (4)0.91948 (16)0.0626 (16)
C230.7777 (8)0.3001 (4)0.72825 (15)0.0540 (14)
C240.8709 (7)0.3303 (4)0.67579 (15)0.0520 (12)
C251.1018 (9)0.2412 (5)0.6690 (2)0.0782 (17)
C261.1972 (10)0.2776 (5)0.6166 (2)0.088 (2)
C271.2156 (8)0.4178 (4)0.60792 (17)0.0626 (17)
C280.9834 (9)0.5085 (5)0.6117 (2)0.0756 (19)
C290.8827 (10)0.4715 (5)0.6639 (2)0.079 (2)
C301.3310 (8)0.4554 (5)0.55920 (18)0.0623 (17)
H1A0.890900.772700.510300.1370*
H1B0.919400.899600.474200.1370*
H1C0.669500.877700.484100.1370*
H1N0.441 (7)0.843 (3)0.7708 (15)0.0490*
H30.783401.007000.623400.0790*
H40.562500.964200.692500.0710*
H4O1.522 (8)0.425 (6)0.9742 (19)0.1160*
H60.290600.737000.619900.0680*
H70.509100.781500.550100.0780*
H8A0.689100.654600.740800.0540*
H8B0.546700.578100.778900.0540*
H90.853500.719100.804100.0660*
H10A0.603600.597600.876500.0860*
H10B0.569000.749400.860600.0860*
H11A0.942500.734400.894600.0870*
H11B0.808000.665400.937400.0870*
H120.993900.461600.919900.0790*
H13A1.274800.431000.862700.0950*
H13B1.242900.582600.847000.0950*
H14A1.039300.516900.786300.0780*
H14B0.904500.447500.828800.0780*
H2N0.825 (5)0.109 (3)0.7335 (15)0.0530*
H10O1.566 (11)0.400 (4)0.525 (3)0.2110*
H16A1.202100.224200.984400.1220*
H16B1.333800.103801.025200.1220*
H16C1.063700.129901.014600.1220*
H181.294400.050800.885300.0840*
H191.035800.023900.817800.0780*
H210.577000.245700.876800.0680*
H220.834100.219100.945000.0750*
H23A0.895200.298100.753900.0640*
H23B0.640600.369200.732000.0640*
H240.759000.319000.651000.0620*
H25A1.086200.152000.673400.0940*
H25B1.212600.244500.695200.0940*
H26A1.350200.219500.614400.1050*
H26B1.094200.266800.590300.1050*
H271.315900.424800.635900.0750*
H28A0.877300.504100.584700.0910*
H28B0.999000.597700.607300.0910*
H29A0.978900.487500.690300.0950*
H29B0.726600.527700.664700.0950*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0355 (5)0.0484 (6)0.0369 (5)0.0078 (4)0.0020 (4)0.0110 (4)
O10.100 (3)0.109 (3)0.055 (2)0.039 (2)0.0312 (18)0.0198 (19)
O20.0573 (16)0.0628 (18)0.0505 (16)0.0279 (14)0.0009 (13)0.0137 (13)
O30.0406 (14)0.0578 (17)0.0509 (16)0.0026 (12)0.0029 (12)0.0122 (13)
O40.067 (2)0.077 (2)0.077 (2)0.0080 (18)0.0345 (17)0.0229 (18)
O50.074 (2)0.086 (2)0.081 (2)0.0099 (18)0.0353 (18)0.039 (2)
N10.0417 (16)0.0421 (18)0.0370 (16)0.0065 (14)0.0031 (13)0.0113 (14)
C10.117 (4)0.097 (4)0.053 (3)0.015 (3)0.032 (3)0.015 (3)
C20.061 (3)0.065 (3)0.046 (2)0.008 (2)0.010 (2)0.006 (2)
C30.068 (3)0.090 (3)0.051 (3)0.037 (3)0.007 (2)0.016 (2)
C40.062 (3)0.081 (3)0.045 (2)0.030 (2)0.0037 (19)0.022 (2)
C50.0376 (18)0.045 (2)0.0357 (19)0.0050 (16)0.0032 (15)0.0091 (15)
C60.074 (3)0.062 (3)0.042 (2)0.025 (2)0.004 (2)0.0172 (19)
C70.092 (3)0.069 (3)0.042 (2)0.025 (3)0.008 (2)0.021 (2)
C80.044 (2)0.048 (2)0.038 (2)0.0042 (17)0.0018 (16)0.0088 (16)
C90.053 (2)0.055 (2)0.052 (2)0.0004 (19)0.0134 (19)0.0212 (19)
C100.055 (3)0.094 (4)0.058 (3)0.000 (2)0.005 (2)0.023 (3)
C110.064 (3)0.091 (4)0.050 (3)0.014 (2)0.018 (2)0.030 (2)
C120.064 (3)0.072 (3)0.052 (3)0.003 (2)0.017 (2)0.013 (2)
C130.061 (3)0.095 (4)0.068 (3)0.013 (3)0.011 (2)0.028 (3)
C140.062 (3)0.068 (3)0.056 (3)0.010 (2)0.016 (2)0.026 (2)
C150.050 (2)0.060 (3)0.046 (2)0.007 (2)0.0110 (18)0.0071 (19)
S20.0432 (5)0.0572 (6)0.0409 (5)0.0171 (4)0.0084 (4)0.0179 (4)
O60.075 (2)0.100 (3)0.062 (2)0.0009 (19)0.0193 (17)0.0318 (19)
O70.0440 (15)0.075 (2)0.0540 (17)0.0033 (14)0.0048 (12)0.0222 (14)
O80.0729 (19)0.069 (2)0.0600 (18)0.0405 (16)0.0159 (15)0.0261 (15)
O90.156 (4)0.072 (3)0.127 (4)0.008 (3)0.088 (3)0.008 (2)
O100.192 (5)0.078 (3)0.140 (4)0.023 (3)0.113 (4)0.004 (3)
N20.0474 (18)0.0482 (19)0.0406 (17)0.0116 (15)0.0096 (14)0.0159 (14)
C160.101 (4)0.076 (3)0.065 (3)0.014 (3)0.024 (3)0.018 (3)
C170.062 (3)0.061 (3)0.044 (2)0.012 (2)0.0043 (19)0.0124 (19)
C180.051 (2)0.089 (3)0.063 (3)0.009 (2)0.000 (2)0.032 (3)
C190.056 (2)0.087 (3)0.053 (3)0.004 (2)0.006 (2)0.036 (2)
C200.0407 (19)0.048 (2)0.0372 (19)0.0119 (16)0.0054 (15)0.0102 (16)
C210.060 (2)0.055 (3)0.050 (2)0.001 (2)0.0001 (19)0.0207 (19)
C220.077 (3)0.058 (3)0.051 (2)0.003 (2)0.002 (2)0.025 (2)
C230.067 (3)0.053 (2)0.048 (2)0.020 (2)0.0138 (19)0.0184 (19)
C240.058 (2)0.052 (2)0.049 (2)0.0171 (19)0.0115 (18)0.0132 (18)
C250.072 (3)0.067 (3)0.077 (3)0.001 (2)0.015 (3)0.012 (2)
C260.105 (4)0.058 (3)0.088 (4)0.004 (3)0.055 (3)0.004 (3)
C270.065 (3)0.067 (3)0.058 (3)0.024 (2)0.014 (2)0.007 (2)
C280.083 (3)0.056 (3)0.083 (4)0.016 (2)0.026 (3)0.003 (2)
C290.100 (4)0.057 (3)0.084 (4)0.021 (3)0.042 (3)0.023 (3)
C300.067 (3)0.056 (3)0.065 (3)0.018 (2)0.021 (2)0.011 (2)
Geometric parameters (Å, º) top
S1—O21.424 (3)C8—H8B0.9700
S1—O31.432 (3)C9—H90.9800
S1—N11.616 (3)C10—H10A0.9700
S1—C51.766 (4)C10—H10B0.9700
S2—O81.428 (3)C11—H11A0.9700
S2—N21.622 (3)C11—H11B0.9700
S2—O71.426 (3)C12—H120.9800
S2—C201.755 (4)C13—H13A0.9700
O1—C11.427 (7)C13—H13B0.9700
O1—C21.359 (6)C14—H14A0.9700
O4—C151.287 (5)C14—H14B0.9700
O5—C151.220 (5)C17—C181.390 (6)
O4—H4O0.83 (5)C17—C221.369 (6)
O6—C161.432 (6)C18—C191.367 (6)
O6—C171.356 (6)C19—C201.374 (6)
O9—C301.211 (7)C20—C211.369 (6)
O10—C301.236 (7)C21—C221.378 (6)
O10—H10O0.82 (7)C23—C241.512 (6)
N1—C81.473 (5)C24—C291.510 (7)
N1—H1N0.83 (4)C24—C251.489 (7)
N2—C231.465 (5)C25—C261.527 (8)
N2—H2N0.85 (3)C26—C271.511 (7)
C2—C31.386 (6)C27—C281.486 (7)
C2—C71.367 (7)C27—C301.503 (7)
C3—C41.372 (6)C28—C291.537 (8)
C4—C51.378 (5)C16—H16A0.9600
C5—C61.373 (5)C16—H16B0.9600
C6—C71.382 (6)C16—H16C0.9600
C8—C91.493 (6)C18—H180.9300
C9—C101.459 (6)C19—H190.9300
C9—C141.515 (6)C21—H210.9300
C10—C111.545 (7)C22—H220.9300
C11—C121.523 (7)C23—H23A0.9700
C12—C131.456 (7)C23—H23B0.9700
C12—C151.518 (6)C24—H240.9800
C13—C141.529 (7)C25—H25A0.9700
C1—H1B0.9600C25—H25B0.9700
C1—H1C0.9600C26—H26A0.9700
C1—H1A0.9600C26—H26B0.9700
C3—H30.9300C27—H270.9800
C4—H40.9300C28—H28A0.9700
C6—H60.9300C28—H28B0.9700
C7—H70.9300C29—H29A0.9700
C8—H8A0.9700C29—H29B0.9700
S2···H25Bi3.1900H4O···C15iii2.66 (5)
O3···N2ii3.024 (4)H4O···O5iii1.84 (5)
O4···O5iii2.660 (5)H6···O22.5500
O5···O4iii2.660 (5)H7···C12.5400
O5···C15iii3.411 (6)H7···H1C2.2100
O6···C16iv3.378 (7)H7···H1A2.4800
O8···N1v2.961 (4)H8A···C52.8400
O9···O10vi2.631 (8)H8A···H14A2.4100
O9···C30vi3.412 (7)H8B···H13Bi2.5500
O10···C30vi3.394 (7)H8B···H14B2.4700
O10···O9vi2.631 (8)H8B···O22.7900
O1···H1Bvii2.7100H9···H13B2.5500
O2···H29Ai2.8700H9···H1N2.5400
O2···H62.5500H9···H11A2.5100
O2···H14Ai2.7500H10A···H13Bi2.3300
O2···H8B2.7900H10A···H14B2.5800
O3···H19ii2.6900H10A···H122.5500
O3···H25Aii2.5400H10A···C13i3.0200
O3···H2Nii2.18 (3)H10A···C15i2.9700
O4···H16A2.7400H10B···H1N2.4700
O4···H4Oiii2.85 (6)H10B···N12.6100
O4···H22viii2.8400H10B···H18ii2.5300
O4···H13A2.5300H10O···O9vi1.89 (8)
O5···H11B2.6700H10O···H10Ovi2.27 (8)
O5···H11A2.7500H10O···C30vi2.65 (7)
O5···H4Oiii1.84 (5)H10O···O10vi2.76 (6)
O6···H16Biv2.5900H11A···H13B2.5900
O7···H212.5100H11A···H92.5100
O7···H25Bi2.8000H11A···O52.7500
O7···H23B2.6200H11B···O52.6700
O8···H1Nv2.14 (3)H11B···C16xiii2.9300
O8···H4v2.6300H11B···H16Axiii2.5700
O9···H28B2.5400H12···H14B2.5200
O9···H1A2.8000H12···H10A2.5500
O9···H10Ovi1.89 (8)H13A···H21viii2.2900
O10···H26A2.4900H13A···O42.5300
O10···H10Ovi2.76 (6)H13B···H8Bviii2.5500
N1···O8ix2.961 (4)H13B···C8viii3.0800
N2···O3x3.024 (4)H13B···C10viii3.0200
N1···H10B2.6100H13B···H11A2.5900
N1···H42.8900H13B···H92.5500
N2···H25A2.7500H13B···H10Aviii2.3300
C15···O5iii3.411 (6)H14A···H8A2.4100
C16···O6iv3.378 (7)H14A···O2viii2.7500
C30···O10vi3.394 (7)H14B···H8B2.4700
C30···O9vi3.412 (7)H14B···H10A2.5800
C1···H26Bxi2.9600H14B···H122.5200
C1···H72.5400H16A···O42.7400
C2···H1Cxii2.9900H16A···C222.8300
C3···H26Aii3.0200H16A···H222.4400
C4···H1N2.95 (4)H16A···H11Bxiii2.5700
C5···H8A2.8400H16B···O6iv2.5900
C6···H29B3.0600H16C···C222.6900
C7···H1C2.6900H16C···H222.2200
C7···H1A2.8500H16C···C17xiv2.9000
C8···H13Bi3.0800H18···H10Bx2.5300
C10···H13Bi3.0200H19···O3x2.6900
C10···H1N2.98 (4)H19···H2N2.5700
C13···H10Aviii3.0200H21···O72.5100
C15···H10Aviii2.9700H21···H13Ai2.2900
C15···H4Oiii2.66 (5)H22···O4i2.8400
C16···H222.5300H22···C162.5300
C16···H11Bxiii2.9300H22···H16A2.4400
C17···H16Cxiv2.9000H22···H16C2.2200
C19···H2N3.01 (4)H23A···C202.9500
C20···H23A2.9500H23A···H25B2.4600
C22···H16C2.6900H23A···H29A2.5500
C22···H16A2.8300H23B···O72.6200
C25···H2N2.81 (3)H23B···H29B2.3900
C30···H10Ovi2.65 (7)H24···H26B2.5700
H1A···O92.8000H24···H27i2.5800
H1A···C72.8500H25A···O3x2.5400
H1A···H72.4800H25A···N22.7500
H1B···O1vii2.7100H25A···H2N2.2900
H1C···C72.6900H25B···S2viii3.1900
H1C···H72.2100H25B···O7viii2.8000
H1C···C2xii2.9900H25B···H23A2.4600
H1N···O8ix2.14 (3)H25B···H272.4700
H1N···C42.95 (4)H26A···O102.4900
H1N···C102.98 (4)H26A···C3x3.0200
H1N···H42.4600H26B···H242.5700
H1N···H92.5400H26B···H28A2.5200
H1N···H10B2.4700H26B···C1xi2.9600
H2N···C252.81 (3)H27···H24viii2.5800
H2N···O3x2.18 (3)H27···H25B2.4700
H2N···C193.01 (4)H27···H29A2.4900
H2N···H192.5700H28A···H26B2.5200
H2N···H25A2.2900H28B···O92.5400
H4···O8ix2.6300H29A···O2viii2.8700
H4···N12.8900H29A···H23A2.5500
H4···H1N2.4600H29A···H272.4900
H4O···O4iii2.85 (6)H29B···C63.0600
H4O···H4Oiii2.26 (8)H29B···H23B2.3900
O2—S1—O3119.03 (18)C13—C12—H12107.00
O2—S1—N1108.36 (17)C12—C13—H13B109.00
O2—S1—C5107.61 (16)C12—C13—H13A109.00
O3—S1—N1105.26 (16)C14—C13—H13B109.00
O3—S1—C5108.38 (16)H13A—C13—H13B108.00
N1—S1—C5107.74 (16)C14—C13—H13A109.00
O8—S2—C20107.74 (19)C9—C14—H14A109.00
N2—S2—C20107.95 (17)H14A—C14—H14B108.00
O7—S2—N2107.77 (17)C13—C14—H14A109.00
O7—S2—C20107.64 (18)C13—C14—H14B109.00
O7—S2—O8119.76 (18)C9—C14—H14B109.00
O8—S2—N2105.49 (17)O6—C17—C18115.2 (4)
C1—O1—C2117.8 (4)O6—C17—C22125.2 (4)
C15—O4—H4O107 (4)C18—C17—C22119.6 (4)
C16—O6—C17117.8 (4)C17—C18—C19120.2 (5)
C30—O10—H10O110 (3)C18—C19—C20120.1 (4)
S1—N1—C8118.3 (2)S2—C20—C19119.8 (3)
S1—N1—H1N106 (3)S2—C20—C21120.5 (3)
C8—N1—H1N118 (3)C19—C20—C21119.8 (4)
S2—N2—C23118.3 (3)C20—C21—C22120.6 (4)
C23—N2—H2N115 (2)C17—C22—C21119.8 (4)
S2—N2—H2N108 (3)N2—C23—C24111.9 (3)
C3—C2—C7119.8 (4)C25—C24—C29110.6 (4)
O1—C2—C7125.5 (4)C23—C24—C29110.2 (4)
O1—C2—C3114.7 (4)C23—C24—C25113.5 (4)
C2—C3—C4120.2 (4)C24—C25—C26112.4 (4)
C3—C4—C5120.1 (4)C25—C26—C27110.4 (4)
C4—C5—C6119.6 (4)C26—C27—C28110.6 (4)
S1—C5—C4120.1 (3)C26—C27—C30112.9 (4)
S1—C5—C6120.3 (3)C28—C27—C30112.6 (4)
C5—C6—C7120.6 (4)C27—C28—C29110.3 (4)
C2—C7—C6119.8 (4)C24—C29—C28113.3 (4)
N1—C8—C9112.4 (3)O9—C30—O10121.1 (5)
C10—C9—C14111.5 (4)O9—C30—C27120.7 (5)
C8—C9—C14109.5 (4)O10—C30—C27118.1 (5)
C8—C9—C10117.0 (4)O6—C16—H16A110.00
C9—C10—C11111.9 (4)O6—C16—H16B109.00
C10—C11—C12110.6 (4)O6—C16—H16C109.00
C11—C12—C13111.7 (4)H16A—C16—H16B109.00
C13—C12—C15112.8 (4)H16A—C16—H16C109.00
C11—C12—C15111.9 (4)H16B—C16—H16C109.00
C12—C13—C14112.1 (4)C17—C18—H18120.00
C9—C14—C13111.6 (4)C19—C18—H18120.00
O4—C15—O5122.4 (4)C18—C19—H19120.00
O4—C15—C12114.3 (4)C20—C19—H19120.00
O5—C15—C12123.3 (4)C20—C21—H21120.00
H1A—C1—H1B109.00C22—C21—H21120.00
H1A—C1—H1C109.00C17—C22—H22120.00
H1B—C1—H1C110.00C21—C22—H22120.00
O1—C1—H1B109.00N2—C23—H23A109.00
O1—C1—H1C109.00N2—C23—H23B109.00
O1—C1—H1A110.00C24—C23—H23A109.00
C4—C3—H3120.00C24—C23—H23B109.00
C2—C3—H3120.00H23A—C23—H23B108.00
C5—C4—H4120.00C23—C24—H24107.00
C3—C4—H4120.00C25—C24—H24107.00
C7—C6—H6120.00C29—C24—H24107.00
C5—C6—H6120.00C24—C25—H25A109.00
C2—C7—H7120.00C24—C25—H25B109.00
C6—C7—H7120.00C26—C25—H25A109.00
C9—C8—H8A109.00C26—C25—H25B109.00
C9—C8—H8B109.00H25A—C25—H25B108.00
H8A—C8—H8B108.00C25—C26—H26A110.00
N1—C8—H8B109.00C25—C26—H26B110.00
N1—C8—H8A109.00C27—C26—H26A110.00
C10—C9—H9106.00C27—C26—H26B110.00
C14—C9—H9106.00H26A—C26—H26B108.00
C8—C9—H9106.00C26—C27—H27107.00
C9—C10—H10B109.00C28—C27—H27107.00
C11—C10—H10A109.00C30—C27—H27107.00
C11—C10—H10B109.00C27—C28—H28A110.00
C9—C10—H10A109.00C27—C28—H28B110.00
H10A—C10—H10B108.00C29—C28—H28A110.00
C12—C11—H11A110.00C29—C28—H28B110.00
C12—C11—H11B110.00H28A—C28—H28B108.00
H11A—C11—H11B108.00C24—C29—H29A109.00
C10—C11—H11A110.00C24—C29—H29B109.00
C10—C11—H11B110.00C28—C29—H29A109.00
C15—C12—H12107.00C28—C29—H29B109.00
C11—C12—H12107.00H29A—C29—H29B108.00
O2—S1—N1—C851.9 (3)C10—C9—C14—C1354.1 (5)
O3—S1—N1—C8179.8 (3)C8—C9—C14—C13174.8 (4)
C5—S1—N1—C864.3 (3)C9—C10—C11—C1254.7 (5)
O2—S1—C5—C4163.4 (3)C10—C11—C12—C1354.4 (5)
O2—S1—C5—C616.4 (4)C10—C11—C12—C15178.1 (4)
O3—S1—C5—C466.7 (3)C13—C12—C15—O5130.0 (5)
O3—S1—C5—C6113.5 (3)C15—C12—C13—C14178.3 (4)
N1—S1—C5—C446.8 (3)C13—C12—C15—O451.7 (6)
N1—S1—C5—C6133.1 (3)C11—C12—C13—C1454.7 (6)
C20—S2—N2—C2365.3 (3)C11—C12—C15—O4178.7 (4)
O7—S2—C20—C19173.3 (3)C11—C12—C15—O53.0 (6)
O7—S2—C20—C216.8 (4)C12—C13—C14—C954.2 (5)
O8—S2—C20—C1956.2 (4)O6—C17—C18—C19178.8 (4)
O8—S2—C20—C21123.7 (3)C22—C17—C18—C190.6 (7)
N2—S2—C20—C1957.3 (4)O6—C17—C22—C21178.9 (4)
N2—S2—C20—C21122.9 (3)C18—C17—C22—C210.4 (7)
O7—S2—N2—C2350.7 (3)C17—C18—C19—C200.5 (7)
O8—S2—N2—C23179.7 (3)C18—C19—C20—S2179.9 (4)
C1—O1—C2—C3172.6 (4)C18—C19—C20—C210.3 (7)
C1—O1—C2—C78.9 (7)S2—C20—C21—C22180.0 (3)
C16—O6—C17—C18174.6 (4)C19—C20—C21—C220.1 (6)
C16—O6—C17—C226.1 (7)C20—C21—C22—C170.1 (7)
S1—N1—C8—C9168.8 (3)N2—C23—C24—C2567.8 (5)
S2—N2—C23—C24173.2 (3)N2—C23—C24—C29167.6 (4)
O1—C2—C3—C4179.5 (4)C23—C24—C25—C26177.4 (4)
C7—C2—C3—C40.9 (7)C29—C24—C25—C2652.9 (5)
O1—C2—C7—C6179.7 (4)C23—C24—C29—C28178.2 (4)
C3—C2—C7—C61.3 (7)C25—C24—C29—C2851.9 (6)
C2—C3—C4—C50.2 (7)C24—C25—C26—C2756.8 (6)
C3—C4—C5—C60.9 (6)C25—C26—C27—C2858.6 (6)
C3—C4—C5—S1179.0 (3)C25—C26—C27—C30174.2 (4)
S1—C5—C6—C7179.3 (3)C26—C27—C28—C2957.1 (5)
C4—C5—C6—C70.5 (6)C30—C27—C28—C29175.6 (4)
C5—C6—C7—C20.6 (7)C26—C27—C30—O9155.7 (5)
N1—C8—C9—C1050.4 (5)C26—C27—C30—O1028.1 (7)
N1—C8—C9—C14178.6 (3)C28—C27—C30—O929.7 (7)
C8—C9—C10—C11178.1 (4)C28—C27—C30—O10154.2 (5)
C14—C9—C10—C1154.7 (5)C27—C28—C29—C2454.5 (6)
Symmetry codes: (i) x1, y, z; (ii) x1, y+1, z; (iii) x+3, y+1, z+2; (iv) x+3, y, z+2; (v) x, y1, z; (vi) x+3, y+1, z+1; (vii) x+2, y+2, z+1; (viii) x+1, y, z; (ix) x, y+1, z; (x) x+1, y1, z; (xi) x+2, y+1, z+1; (xii) x+1, y+2, z+1; (xiii) x+2, y+1, z+2; (xiv) x+2, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O8ix0.83 (4)2.14 (3)2.961 (4)173 (3)
N2—H2N···O3x0.85 (3)2.18 (3)3.024 (4)172 (3)
O4—H4O···O5iii0.83 (5)1.84 (5)2.660 (5)166 (6)
O10—H10O···O9vi0.82 (7)1.89 (8)2.631 (8)151 (7)
C6—H6···O20.932.552.918 (5)104
C10—H10B···N10.972.612.945 (5)100
C16—H16B···O6iv0.962.593.378 (7)139
C21—H21···O70.932.512.890 (5)105
C25—H25A···O3x0.972.543.450 (6)157
Symmetry codes: (iii) x+3, y+1, z+2; (iv) x+3, y, z+2; (vi) x+3, y+1, z+1; (ix) x, y+1, z; (x) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC15H21NO5S
Mr327.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)5.9119 (3), 10.7223 (7), 26.6453 (15)
α, β, γ (°)79.736 (3), 89.813 (3), 75.518 (3)
V3)1607.67 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.25 × 0.19 × 0.14
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25440, 5942, 3973
Rint0.048
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.218, 1.03
No. of reflections5942
No. of parameters412
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.92, 0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O8i0.83 (4)2.14 (3)2.961 (4)173 (3)
N2—H2N···O3ii0.85 (3)2.18 (3)3.024 (4)172 (3)
O4—H4O···O5iii0.83 (5)1.84 (5)2.660 (5)166 (6)
O10—H10O···O9iv0.82 (7)1.89 (8)2.631 (8)151 (7)
C16—H16B···O6v0.962.593.378 (7)139
C25—H25A···O3ii0.972.543.450 (6)157
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1, z; (iii) x+3, y+1, z+2; (iv) x+3, y+1, z+1; (v) x+3, y, z+2.
 

Footnotes

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

Acknowledgements

The authors are grateful to the Vice Chancellor of the University of Gujrat, Professor Dr Nizamuddin, for creating a healthy research environment in the campus.

References

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Volume 67| Part 9| September 2011| Pages o2248-o2249
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