organic compounds
Mutual prodrug of cephazolin and benzydamin: 3-[(1-benzyl-1H-indazol-3-yl)oxy]-N,N-dimethylpropan-1-aminium 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate (benzydaminium cephazolinate)
aDepartment of Chemistry, Government College University, Lahore, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the crystal of the title molecular salt, C19H24N3O+·C14H13N8O4S3−, the cations and anions are linked by N—H⋯O hydrogen bonds. Short intramolecular C—H⋯O contacts occur within the anion and intermolecular C—H⋯O and C—H⋯π bonds help to establish the packing.
Related literature
Cephazolin, is a first generation cefalosporin antibiotic and benzydamin hydrochloride is a locally acting non-steroidal anti-inflammatory drug with local anaesthetic and analgesic properties. The title compound was prepared as a mutual prodrug for the treatment of infections and inflamatory conditions. For medicinal background to cephazolin, see: Turnbull (1995). For ring-puckering analysis, see: Cremer & Pople (1975). For graph-set theory, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536809047941/hb5219sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047941/hb5219Isup2.hkl
Cefazolin sodium (0.238 g; 0.1 mol) and benzydamine hydrochloride (0.173 g; 0.01 mol) were dissolved separately in distilled water (50 ml). Ten milliliter of each solution were mixed and left for two days. The colourless needles of (I) thus obtained were filtered out by suction, washed with distilled water and dried under vacuum.
The coordinates of H3N were refined. The H-atoms were positioned geometrically (O–H = 0.82 Å, N–H = 0.86 Å, C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).
Data collection: APEX2 (Bruker, 2007); cell
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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The partial packing of (I), which shows that molecules form polymeric chains and ring motifs. | |
Fig. 3. The partial packing of (I), which shows that molecules form polymeric networks with various ring motifs. |
C19H24N3O+·C14H13N8O4S3− | F(000) = 1600 |
Mr = 763.92 | Dx = 1.413 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 3824 reflections |
a = 44.409 (3) Å | θ = 2.6–26.0° |
b = 7.1777 (5) Å | µ = 0.27 mm−1 |
c = 11.2683 (8) Å | T = 296 K |
β = 90.587 (8)° | Cut needle, colourless |
V = 3591.6 (4) Å3 | 0.24 × 0.14 × 0.12 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 6750 independent reflections |
Radiation source: fine-focus sealed tube | 4092 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 7.60 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
ω scans | h = −54→54 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −8→8 |
Tmin = 0.957, Tmax = 0.968 | l = −13→13 |
34321 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
6750 reflections | Δρmax = 0.36 e Å−3 |
475 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2918 Friedal Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (7) |
C19H24N3O+·C14H13N8O4S3− | V = 3591.6 (4) Å3 |
Mr = 763.92 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 44.409 (3) Å | µ = 0.27 mm−1 |
b = 7.1777 (5) Å | T = 296 K |
c = 11.2683 (8) Å | 0.24 × 0.14 × 0.12 mm |
β = 90.587 (8)° |
Bruker Kappa APEXII CCD diffractometer | 6750 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4092 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.968 | Rint = 0.088 |
34321 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | Δρmax = 0.36 e Å−3 |
S = 1.00 | Δρmin = −0.23 e Å−3 |
6750 reflections | Absolute structure: Flack (1983), 2918 Friedal Pairs |
475 parameters | Absolute structure parameter: −0.07 (7) |
1 restraint |
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 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.14103 (6) | 0.2863 (4) | 0.9240 (3) | 0.0552 (11) | |
N1 | 0.18241 (7) | 0.2542 (4) | 0.7971 (3) | 0.0420 (12) | |
N2 | 0.19416 (7) | 0.3698 (5) | 0.7111 (3) | 0.0433 (12) | |
N3 | 0.06627 (7) | 0.0749 (5) | 1.1012 (3) | 0.0372 (11) | |
C1 | 0.15436 (8) | 0.5181 (5) | 0.7788 (3) | 0.0340 (12) | |
C2 | 0.13236 (9) | 0.6570 (6) | 0.7813 (4) | 0.0510 (17) | |
C3 | 0.13442 (11) | 0.8000 (7) | 0.7038 (4) | 0.0640 (17) | |
C4 | 0.15844 (11) | 0.8115 (6) | 0.6251 (4) | 0.0610 (19) | |
C5 | 0.18016 (10) | 0.6769 (6) | 0.6189 (3) | 0.0490 (17) | |
C6 | 0.17762 (8) | 0.5263 (5) | 0.6969 (3) | 0.0370 (12) | |
C7 | 0.21920 (9) | 0.3080 (6) | 0.6398 (3) | 0.0463 (17) | |
C8 | 0.24923 (8) | 0.3866 (5) | 0.6760 (3) | 0.0353 (12) | |
C9 | 0.25878 (9) | 0.3855 (6) | 0.7933 (4) | 0.0466 (17) | |
C10 | 0.28704 (10) | 0.4478 (6) | 0.8244 (4) | 0.0520 (17) | |
C11 | 0.30587 (9) | 0.5147 (6) | 0.7391 (4) | 0.0484 (17) | |
C12 | 0.29672 (9) | 0.5182 (6) | 0.6231 (4) | 0.0492 (17) | |
C13 | 0.26851 (9) | 0.4546 (6) | 0.5911 (3) | 0.0450 (17) | |
C14 | 0.15916 (9) | 0.3469 (5) | 0.8366 (3) | 0.0393 (16) | |
C15 | 0.14483 (9) | 0.1004 (6) | 0.9660 (4) | 0.0546 (17) | |
C16 | 0.12086 (10) | 0.0662 (8) | 1.0548 (4) | 0.0699 (19) | |
C17 | 0.09024 (9) | 0.0869 (7) | 1.0079 (4) | 0.0636 (19) | |
C18 | 0.06411 (12) | 0.2420 (7) | 1.1765 (4) | 0.089 (3) | |
C19 | 0.03700 (9) | 0.0436 (8) | 1.0420 (4) | 0.0718 (19) | |
S1 | 0.10575 (2) | 0.19304 (14) | 0.49823 (9) | 0.0428 (3) | |
S2 | 0.14745 (2) | 0.56694 (16) | 0.18123 (9) | 0.0463 (4) | |
S3 | 0.20738 (2) | 0.44836 (15) | 0.08659 (9) | 0.0456 (4) | |
O2 | 0.05024 (6) | 0.8249 (3) | 0.3777 (2) | 0.0384 (9) | |
O3 | 0.08047 (6) | 0.7715 (4) | 0.2253 (2) | 0.0547 (11) | |
O4 | 0.02066 (6) | 0.4136 (4) | 0.3861 (2) | 0.0405 (9) | |
O5 | 0.02552 (7) | 0.0728 (4) | 0.7592 (2) | 0.0587 (13) | |
N4 | 0.19862 (7) | 0.4956 (4) | 0.3076 (3) | 0.0406 (12) | |
N5 | 0.22865 (7) | 0.4435 (4) | 0.2966 (3) | 0.0427 (12) | |
N6 | 0.06812 (6) | 0.4815 (4) | 0.4717 (2) | 0.0279 (10) | |
N7 | 0.03965 (6) | 0.0819 (4) | 0.5676 (2) | 0.0315 (10) | |
N8 | 0.02949 (7) | −0.3125 (4) | 0.7545 (3) | 0.0325 (11) | |
N9 | 0.05801 (8) | −0.3400 (5) | 0.7855 (3) | 0.0603 (16) | |
N10 | 0.05818 (10) | −0.4303 (7) | 0.8833 (4) | 0.0751 (17) | |
N11 | 0.02978 (11) | −0.4641 (5) | 0.9184 (3) | 0.0663 (16) | |
C20 | 0.13044 (8) | 0.3791 (5) | 0.4529 (3) | 0.0440 (14) | |
C21 | 0.11584 (8) | 0.5428 (5) | 0.3900 (3) | 0.0317 (12) | |
C22 | 0.08645 (8) | 0.5831 (5) | 0.3948 (3) | 0.0293 (12) | |
C23 | 0.07099 (9) | 0.7410 (5) | 0.3273 (3) | 0.0330 (12) | |
C24 | 0.13782 (8) | 0.6622 (5) | 0.3251 (3) | 0.0396 (14) | |
C25 | 0.18490 (8) | 0.5045 (5) | 0.2061 (3) | 0.0376 (12) | |
C26 | 0.23635 (9) | 0.4134 (5) | 0.1884 (3) | 0.0407 (14) | |
C27 | 0.26722 (9) | 0.3571 (6) | 0.1520 (4) | 0.0570 (17) | |
C28 | 0.07883 (8) | 0.3496 (5) | 0.5621 (3) | 0.0347 (12) | |
C29 | 0.04609 (8) | 0.2771 (5) | 0.5704 (3) | 0.0323 (12) | |
C30 | 0.04024 (8) | 0.3968 (5) | 0.4591 (3) | 0.0289 (12) | |
C31 | 0.02943 (8) | −0.0044 (5) | 0.6644 (3) | 0.0340 (12) | |
C32 | 0.02179 (8) | −0.2078 (5) | 0.6480 (3) | 0.0337 (12) | |
C33 | 0.01254 (10) | −0.3891 (5) | 0.8368 (4) | 0.0479 (17) | |
H2 | 0.11664 | 0.65124 | 0.83513 | 0.0612* | |
H3 | 0.11965 | 0.89190 | 0.70279 | 0.0762* | |
H3N | 0.0701 (8) | −0.035 (5) | 1.148 (3) | 0.0446* | |
H4 | 0.15971 | 0.91434 | 0.57520 | 0.0732* | |
H5 | 0.19589 | 0.68514 | 0.56533 | 0.0588* | |
H7A | 0.21521 | 0.34164 | 0.55778 | 0.0555* | |
H7B | 0.22030 | 0.17314 | 0.64381 | 0.0555* | |
H9 | 0.24592 | 0.34200 | 0.85174 | 0.0560* | |
H10 | 0.29334 | 0.44458 | 0.90336 | 0.0622* | |
H11 | 0.32494 | 0.55774 | 0.76019 | 0.0578* | |
H12 | 0.30960 | 0.56374 | 0.56540 | 0.0593* | |
H13 | 0.26244 | 0.45759 | 0.51190 | 0.0541* | |
H15A | 0.16458 | 0.08557 | 1.00236 | 0.0653* | |
H15B | 0.14299 | 0.01281 | 0.90075 | 0.0653* | |
H16A | 0.12321 | −0.05902 | 1.08589 | 0.0837* | |
H16B | 0.12364 | 0.15230 | 1.12035 | 0.0837* | |
H17A | 0.08661 | −0.00932 | 0.94905 | 0.0766* | |
H17B | 0.08860 | 0.20648 | 0.96821 | 0.0766* | |
H18A | 0.05950 | 0.34834 | 1.12796 | 0.1331* | |
H18B | 0.08295 | 0.26181 | 1.21710 | 0.1331* | |
H18C | 0.04846 | 0.22478 | 1.23366 | 0.1331* | |
H19A | 0.03248 | 0.14682 | 0.99069 | 0.1076* | |
H19B | 0.02159 | 0.03237 | 1.10070 | 0.1076* | |
H19C | 0.03785 | −0.06890 | 0.99605 | 0.1076* | |
H7N | 0.04237 | 0.01975 | 0.50338 | 0.0378* | |
H20A | 0.14087 | 0.42565 | 0.52288 | 0.0529* | |
H20B | 0.14552 | 0.32694 | 0.40083 | 0.0529* | |
H24A | 0.15602 | 0.67492 | 0.37270 | 0.0474* | |
H24B | 0.12927 | 0.78543 | 0.31426 | 0.0474* | |
H27A | 0.27708 | 0.29376 | 0.21663 | 0.0852* | |
H27B | 0.27858 | 0.46598 | 0.13134 | 0.0852* | |
H27C | 0.26590 | 0.27544 | 0.08474 | 0.0852* | |
H28 | 0.08607 | 0.41003 | 0.63503 | 0.0418* | |
H29 | 0.03622 | 0.33403 | 0.63884 | 0.0385* | |
H32A | 0.00044 | −0.22075 | 0.63099 | 0.0402* | |
H32B | 0.03281 | −0.25736 | 0.58121 | 0.0402* | |
H33 | −0.00840 | −0.38952 | 0.83662 | 0.0575* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.058 (2) | 0.0430 (17) | 0.065 (2) | 0.0076 (15) | 0.0274 (16) | 0.0174 (15) |
N1 | 0.036 (2) | 0.044 (2) | 0.046 (2) | 0.0012 (17) | 0.0080 (18) | 0.0076 (17) |
N2 | 0.031 (2) | 0.052 (2) | 0.047 (2) | 0.0036 (18) | 0.0123 (17) | 0.0080 (18) |
N3 | 0.039 (2) | 0.043 (2) | 0.0295 (19) | 0.0030 (18) | 0.0015 (16) | 0.0090 (17) |
C1 | 0.030 (2) | 0.037 (2) | 0.035 (2) | −0.0035 (19) | −0.0037 (19) | 0.0030 (19) |
C2 | 0.049 (3) | 0.050 (3) | 0.054 (3) | 0.008 (2) | 0.007 (2) | 0.009 (2) |
C3 | 0.070 (3) | 0.064 (3) | 0.058 (3) | 0.021 (3) | 0.005 (3) | 0.014 (3) |
C4 | 0.082 (4) | 0.048 (3) | 0.053 (3) | 0.003 (3) | 0.002 (3) | 0.013 (2) |
C5 | 0.054 (3) | 0.054 (3) | 0.039 (3) | −0.015 (3) | 0.001 (2) | 0.010 (2) |
C6 | 0.034 (2) | 0.040 (2) | 0.037 (2) | −0.006 (2) | −0.004 (2) | 0.002 (2) |
C7 | 0.042 (3) | 0.051 (3) | 0.046 (3) | −0.002 (2) | 0.006 (2) | −0.003 (2) |
C8 | 0.034 (2) | 0.036 (2) | 0.036 (2) | 0.0023 (19) | 0.005 (2) | 0.003 (2) |
C9 | 0.049 (3) | 0.049 (3) | 0.042 (3) | −0.007 (2) | 0.008 (2) | 0.001 (2) |
C10 | 0.059 (3) | 0.056 (3) | 0.041 (3) | −0.008 (3) | −0.005 (2) | −0.002 (2) |
C11 | 0.040 (3) | 0.042 (3) | 0.063 (3) | 0.007 (2) | −0.003 (2) | 0.000 (2) |
C12 | 0.041 (3) | 0.052 (3) | 0.055 (3) | 0.004 (2) | 0.014 (2) | 0.009 (2) |
C13 | 0.042 (3) | 0.051 (3) | 0.042 (3) | 0.004 (2) | 0.006 (2) | 0.004 (2) |
C14 | 0.031 (2) | 0.047 (3) | 0.040 (3) | −0.006 (2) | 0.006 (2) | 0.009 (2) |
C15 | 0.042 (3) | 0.054 (3) | 0.068 (3) | 0.005 (2) | 0.010 (2) | 0.015 (3) |
C16 | 0.054 (3) | 0.071 (3) | 0.085 (4) | 0.004 (3) | 0.023 (3) | 0.042 (3) |
C17 | 0.051 (3) | 0.082 (4) | 0.058 (3) | −0.010 (3) | 0.006 (3) | 0.024 (3) |
C18 | 0.128 (5) | 0.061 (4) | 0.077 (4) | 0.019 (3) | −0.010 (4) | −0.030 (3) |
C19 | 0.052 (3) | 0.101 (4) | 0.062 (3) | −0.009 (3) | −0.015 (2) | 0.006 (3) |
S1 | 0.0374 (6) | 0.0314 (5) | 0.0596 (7) | 0.0060 (5) | 0.0004 (5) | 0.0109 (5) |
S2 | 0.0375 (6) | 0.0565 (7) | 0.0448 (7) | −0.0009 (6) | 0.0007 (5) | 0.0019 (6) |
S3 | 0.0463 (7) | 0.0527 (7) | 0.0380 (6) | 0.0001 (6) | 0.0054 (5) | −0.0031 (5) |
O2 | 0.0384 (16) | 0.0316 (15) | 0.0452 (17) | 0.0089 (13) | 0.0084 (14) | 0.0012 (13) |
O3 | 0.067 (2) | 0.0582 (19) | 0.0393 (17) | 0.0184 (16) | 0.0200 (16) | 0.0246 (15) |
O4 | 0.0324 (15) | 0.0485 (17) | 0.0406 (16) | −0.0028 (13) | −0.0041 (14) | 0.0086 (14) |
O5 | 0.106 (3) | 0.0393 (17) | 0.0313 (16) | −0.0094 (17) | 0.0191 (16) | −0.0010 (15) |
N4 | 0.037 (2) | 0.046 (2) | 0.039 (2) | 0.0003 (16) | 0.0038 (16) | 0.0039 (16) |
N5 | 0.038 (2) | 0.047 (2) | 0.043 (2) | 0.0016 (18) | 0.0012 (17) | 0.0032 (18) |
N6 | 0.0282 (18) | 0.0253 (17) | 0.0302 (17) | −0.0001 (14) | 0.0004 (14) | 0.0099 (14) |
N7 | 0.0414 (19) | 0.0239 (17) | 0.0293 (18) | −0.0033 (15) | 0.0101 (15) | 0.0011 (15) |
N8 | 0.038 (2) | 0.0287 (16) | 0.0308 (19) | −0.0024 (16) | 0.0055 (16) | 0.0022 (16) |
N9 | 0.044 (2) | 0.080 (3) | 0.057 (3) | 0.010 (2) | 0.000 (2) | 0.016 (2) |
N10 | 0.074 (3) | 0.090 (3) | 0.061 (3) | 0.028 (3) | −0.009 (2) | 0.022 (3) |
N11 | 0.096 (3) | 0.059 (3) | 0.044 (2) | 0.001 (3) | 0.003 (2) | 0.020 (2) |
C20 | 0.036 (2) | 0.043 (2) | 0.053 (3) | −0.003 (2) | 0.000 (2) | 0.011 (2) |
C21 | 0.031 (2) | 0.027 (2) | 0.037 (2) | −0.0021 (18) | 0.0007 (18) | 0.0008 (18) |
C22 | 0.030 (2) | 0.028 (2) | 0.030 (2) | −0.0067 (18) | 0.0040 (17) | 0.0024 (18) |
C23 | 0.036 (2) | 0.028 (2) | 0.035 (2) | −0.0032 (18) | −0.005 (2) | 0.0028 (19) |
C24 | 0.035 (2) | 0.034 (2) | 0.050 (3) | −0.0034 (19) | 0.0070 (19) | 0.004 (2) |
C25 | 0.040 (2) | 0.035 (2) | 0.038 (2) | −0.0023 (19) | 0.007 (2) | 0.0035 (19) |
C26 | 0.037 (2) | 0.041 (2) | 0.044 (3) | −0.001 (2) | 0.003 (2) | −0.003 (2) |
C27 | 0.044 (3) | 0.062 (3) | 0.065 (3) | 0.006 (2) | 0.008 (2) | 0.001 (2) |
C28 | 0.039 (2) | 0.035 (2) | 0.030 (2) | 0.0001 (19) | 0.0014 (19) | 0.0055 (18) |
C29 | 0.039 (2) | 0.029 (2) | 0.029 (2) | 0.0000 (19) | 0.0081 (18) | 0.0008 (18) |
C30 | 0.029 (2) | 0.029 (2) | 0.029 (2) | 0.0037 (19) | 0.0095 (19) | −0.0001 (18) |
C31 | 0.036 (2) | 0.036 (2) | 0.030 (2) | −0.0018 (19) | 0.0035 (19) | 0.0063 (19) |
C32 | 0.036 (2) | 0.033 (2) | 0.032 (2) | −0.0091 (18) | 0.0000 (18) | 0.0061 (18) |
C33 | 0.055 (3) | 0.048 (3) | 0.041 (3) | −0.007 (2) | 0.009 (2) | 0.008 (2) |
S1—C20 | 1.805 (4) | C11—C12 | 1.365 (6) |
S1—C28 | 1.797 (4) | C12—C13 | 1.378 (6) |
S2—C24 | 1.815 (4) | C15—C16 | 1.489 (6) |
S2—C25 | 1.742 (4) | C16—C17 | 1.461 (6) |
S3—C26 | 1.733 (4) | C2—H2 | 0.9300 |
S3—C25 | 1.732 (4) | C3—H3 | 0.9300 |
O1—C15 | 1.425 (5) | C4—H4 | 0.9300 |
O1—C14 | 1.350 (5) | C5—H5 | 0.9300 |
O2—C23 | 1.243 (5) | C7—H7B | 0.9700 |
O3—C23 | 1.247 (4) | C7—H7A | 0.9700 |
O4—C30 | 1.197 (4) | C9—H9 | 0.9300 |
O5—C31 | 1.217 (4) | C10—H10 | 0.9300 |
N1—N2 | 1.382 (5) | C11—H11 | 0.9300 |
N1—C14 | 1.310 (5) | C12—H12 | 0.9300 |
N2—C7 | 1.448 (5) | C13—H13 | 0.9300 |
N2—C6 | 1.351 (5) | C15—H15B | 0.9700 |
N3—C17 | 1.506 (5) | C15—H15A | 0.9700 |
N3—C18 | 1.473 (6) | C16—H16A | 0.9700 |
N3—C19 | 1.472 (5) | C16—H16B | 0.9700 |
N3—H3N | 0.96 (4) | C17—H17A | 0.9700 |
N4—N5 | 1.392 (4) | C17—H17B | 0.9700 |
N4—C25 | 1.292 (5) | C18—H18B | 0.9600 |
N5—C26 | 1.288 (5) | C18—H18A | 0.9600 |
N6—C28 | 1.466 (4) | C18—H18C | 0.9600 |
N6—C30 | 1.385 (4) | C19—H19C | 0.9600 |
N6—C22 | 1.400 (4) | C19—H19B | 0.9600 |
N7—C31 | 1.338 (4) | C19—H19A | 0.9600 |
N7—C29 | 1.430 (5) | C20—C21 | 1.515 (5) |
N8—N9 | 1.325 (5) | C21—C24 | 1.496 (5) |
N8—C33 | 1.320 (5) | C21—C22 | 1.339 (5) |
N8—C32 | 1.454 (5) | C22—C23 | 1.524 (5) |
N9—N10 | 1.279 (6) | C26—C27 | 1.491 (6) |
N10—N11 | 1.348 (7) | C28—C29 | 1.548 (5) |
N11—C33 | 1.307 (6) | C29—C30 | 1.540 (5) |
N7—H7N | 0.8600 | C31—C32 | 1.510 (5) |
C1—C14 | 1.406 (5) | C20—H20A | 0.9700 |
C1—C2 | 1.396 (5) | C20—H20B | 0.9700 |
C1—C6 | 1.393 (5) | C24—H24A | 0.9700 |
C2—C3 | 1.351 (7) | C24—H24B | 0.9700 |
C3—C4 | 1.397 (7) | C27—H27A | 0.9600 |
C4—C5 | 1.368 (6) | C27—H27B | 0.9600 |
C5—C6 | 1.399 (5) | C27—H27C | 0.9600 |
C7—C8 | 1.501 (5) | C28—H28 | 0.9800 |
C8—C9 | 1.384 (6) | C29—H29 | 0.9800 |
C8—C13 | 1.380 (5) | C32—H32A | 0.9700 |
C9—C10 | 1.374 (6) | C32—H32B | 0.9700 |
C10—C11 | 1.368 (6) | C33—H33 | 0.9300 |
C20—S1—C28 | 93.40 (17) | C15—C16—H16B | 109.00 |
C24—S2—C25 | 100.75 (17) | C17—C16—H16B | 109.00 |
C25—S3—C26 | 87.07 (17) | H16A—C16—H16B | 108.00 |
C14—O1—C15 | 118.3 (3) | C17—C16—H16A | 109.00 |
N2—N1—C14 | 103.8 (3) | C16—C17—H17A | 109.00 |
C6—N2—C7 | 127.5 (3) | C16—C17—H17B | 109.00 |
N1—N2—C6 | 111.9 (3) | H17A—C17—H17B | 108.00 |
N1—N2—C7 | 120.2 (3) | N3—C17—H17B | 109.00 |
C17—N3—C18 | 114.0 (4) | N3—C17—H17A | 109.00 |
C17—N3—C19 | 108.6 (3) | N3—C18—H18B | 109.00 |
C18—N3—C19 | 108.8 (4) | N3—C18—H18A | 110.00 |
C17—N3—H3N | 108 (2) | H18A—C18—H18C | 109.00 |
C18—N3—H3N | 111 (2) | N3—C18—H18C | 109.00 |
C19—N3—H3N | 106 (2) | H18A—C18—H18B | 109.00 |
N5—N4—C25 | 112.2 (3) | H18B—C18—H18C | 109.00 |
N4—N5—C26 | 113.2 (3) | N3—C19—H19B | 109.00 |
C22—N6—C30 | 133.6 (3) | N3—C19—H19C | 109.00 |
C22—N6—C28 | 125.4 (3) | H19A—C19—H19C | 109.00 |
C28—N6—C30 | 94.1 (3) | H19B—C19—H19C | 109.00 |
C29—N7—C31 | 120.3 (3) | H19A—C19—H19B | 109.00 |
N9—N8—C32 | 120.7 (3) | N3—C19—H19A | 109.00 |
C32—N8—C33 | 131.6 (3) | S1—C20—C21 | 116.6 (3) |
N9—N8—C33 | 107.6 (3) | C22—C21—C24 | 122.5 (3) |
N8—N9—N10 | 107.5 (3) | C20—C21—C22 | 124.2 (3) |
N9—N10—N11 | 110.3 (4) | C20—C21—C24 | 113.3 (3) |
N10—N11—C33 | 105.2 (4) | N6—C22—C23 | 115.8 (3) |
C29—N7—H7N | 120.00 | N6—C22—C21 | 119.1 (3) |
C31—N7—H7N | 120.00 | C21—C22—C23 | 125.1 (3) |
C6—C1—C14 | 103.5 (3) | O2—C23—C22 | 117.7 (3) |
C2—C1—C6 | 120.5 (3) | O2—C23—O3 | 126.5 (3) |
C2—C1—C14 | 135.8 (4) | O3—C23—C22 | 115.8 (3) |
C1—C2—C3 | 118.5 (4) | S2—C24—C21 | 112.5 (2) |
C2—C3—C4 | 120.8 (4) | S2—C25—N4 | 126.6 (3) |
C3—C4—C5 | 122.3 (4) | S2—C25—S3 | 119.5 (2) |
C4—C5—C6 | 116.9 (4) | S3—C25—N4 | 114.0 (3) |
N2—C6—C1 | 107.0 (3) | S3—C26—C27 | 122.4 (3) |
C1—C6—C5 | 120.9 (3) | S3—C26—N5 | 113.6 (3) |
N2—C6—C5 | 132.1 (3) | N5—C26—C27 | 124.0 (4) |
N2—C7—C8 | 114.8 (3) | N6—C28—C29 | 87.8 (2) |
C7—C8—C9 | 121.4 (3) | S1—C28—C29 | 116.3 (2) |
C7—C8—C13 | 120.0 (3) | S1—C28—N6 | 109.8 (2) |
C9—C8—C13 | 118.6 (3) | N7—C29—C28 | 121.0 (3) |
C8—C9—C10 | 120.8 (4) | N7—C29—C30 | 119.8 (3) |
C9—C10—C11 | 119.9 (4) | C28—C29—C30 | 85.1 (3) |
C10—C11—C12 | 120.1 (4) | O4—C30—N6 | 132.0 (3) |
C11—C12—C13 | 120.4 (4) | N6—C30—C29 | 91.0 (3) |
C8—C13—C12 | 120.3 (3) | O4—C30—C29 | 137.0 (3) |
N1—C14—C1 | 113.8 (3) | O5—C31—C32 | 120.9 (3) |
O1—C14—N1 | 124.2 (3) | O5—C31—N7 | 123.9 (3) |
O1—C14—C1 | 122.1 (3) | N7—C31—C32 | 115.2 (3) |
O1—C15—C16 | 107.1 (4) | N8—C32—C31 | 110.4 (3) |
C15—C16—C17 | 114.2 (4) | N8—C33—N11 | 109.4 (4) |
N3—C17—C16 | 113.8 (4) | S1—C20—H20A | 108.00 |
C1—C2—H2 | 121.00 | S1—C20—H20B | 108.00 |
C3—C2—H2 | 121.00 | C21—C20—H20A | 108.00 |
C4—C3—H3 | 120.00 | C21—C20—H20B | 108.00 |
C2—C3—H3 | 120.00 | H20A—C20—H20B | 107.00 |
C3—C4—H4 | 119.00 | S2—C24—H24A | 109.00 |
C5—C4—H4 | 119.00 | S2—C24—H24B | 109.00 |
C6—C5—H5 | 122.00 | C21—C24—H24A | 109.00 |
C4—C5—H5 | 122.00 | C21—C24—H24B | 109.00 |
N2—C7—H7A | 109.00 | H24A—C24—H24B | 108.00 |
C8—C7—H7B | 109.00 | C26—C27—H27A | 109.00 |
N2—C7—H7B | 109.00 | C26—C27—H27B | 109.00 |
C8—C7—H7A | 109.00 | C26—C27—H27C | 110.00 |
H7A—C7—H7B | 108.00 | H27A—C27—H27B | 109.00 |
C10—C9—H9 | 120.00 | H27A—C27—H27C | 109.00 |
C8—C9—H9 | 120.00 | H27B—C27—H27C | 109.00 |
C9—C10—H10 | 120.00 | S1—C28—H28 | 113.00 |
C11—C10—H10 | 120.00 | N6—C28—H28 | 113.00 |
C12—C11—H11 | 120.00 | C29—C28—H28 | 113.00 |
C10—C11—H11 | 120.00 | N7—C29—H29 | 110.00 |
C13—C12—H12 | 120.00 | C28—C29—H29 | 110.00 |
C11—C12—H12 | 120.00 | C30—C29—H29 | 110.00 |
C8—C13—H13 | 120.00 | N8—C32—H32A | 110.00 |
C12—C13—H13 | 120.00 | N8—C32—H32B | 110.00 |
O1—C15—H15B | 110.00 | C31—C32—H32A | 110.00 |
C16—C15—H15A | 110.00 | C31—C32—H32B | 110.00 |
O1—C15—H15A | 110.00 | H32A—C32—H32B | 108.00 |
H15A—C15—H15B | 109.00 | N8—C33—H33 | 125.00 |
C16—C15—H15B | 110.00 | N11—C33—H33 | 125.00 |
C15—C16—H16A | 109.00 | ||
C20—S1—C28—C29 | 155.3 (3) | N8—N9—N10—N11 | 0.1 (5) |
C20—S1—C28—N6 | 57.8 (3) | N9—N10—N11—C33 | −0.1 (5) |
C28—S1—C20—C21 | −47.1 (3) | N10—N11—C33—N8 | 0.2 (5) |
C24—S2—C25—N4 | 12.6 (4) | C2—C1—C6—N2 | −176.6 (3) |
C24—S2—C25—S3 | −167.0 (2) | C2—C1—C6—C5 | 2.6 (6) |
C25—S2—C24—C21 | −111.3 (3) | C14—C1—C2—C3 | −175.0 (4) |
C25—S3—C26—C27 | −179.3 (3) | C14—C1—C6—C5 | 178.4 (3) |
C26—S3—C25—N4 | −0.1 (3) | C2—C1—C14—O1 | −5.2 (7) |
C25—S3—C26—N5 | −0.4 (3) | C14—C1—C6—N2 | −0.8 (4) |
C26—S3—C25—S2 | 179.6 (2) | C6—C1—C2—C3 | −0.9 (6) |
C14—O1—C15—C16 | −176.1 (3) | C6—C1—C14—N1 | −0.5 (4) |
C15—O1—C14—C1 | 171.1 (3) | C2—C1—C14—N1 | 174.4 (4) |
C15—O1—C14—N1 | −8.4 (5) | C6—C1—C14—O1 | 179.9 (3) |
N2—N1—C14—C1 | 1.4 (4) | C1—C2—C3—C4 | −1.7 (7) |
C14—N1—N2—C7 | −175.3 (3) | C2—C3—C4—C5 | 2.7 (7) |
N2—N1—C14—O1 | −179.0 (3) | C3—C4—C5—C6 | −1.0 (6) |
C14—N1—N2—C6 | −1.9 (4) | C4—C5—C6—C1 | −1.6 (6) |
N1—N2—C6—C5 | −177.3 (4) | C4—C5—C6—N2 | 177.3 (4) |
C7—N2—C6—C5 | −4.6 (7) | N2—C7—C8—C9 | 48.2 (5) |
N1—N2—C7—C8 | −102.2 (4) | N2—C7—C8—C13 | −134.6 (4) |
C6—N2—C7—C8 | 85.6 (5) | C7—C8—C13—C12 | −176.7 (4) |
C7—N2—C6—C1 | 174.5 (3) | C9—C8—C13—C12 | 0.6 (6) |
N1—N2—C6—C1 | 1.7 (4) | C13—C8—C9—C10 | −1.1 (6) |
C19—N3—C17—C16 | −164.0 (4) | C7—C8—C9—C10 | 176.1 (4) |
C18—N3—C17—C16 | 74.5 (5) | C8—C9—C10—C11 | 1.1 (6) |
C25—N4—N5—C26 | −0.7 (4) | C9—C10—C11—C12 | −0.5 (7) |
N5—N4—C25—S3 | 0.4 (4) | C10—C11—C12—C13 | 0.0 (7) |
N5—N4—C25—S2 | −179.2 (3) | C11—C12—C13—C8 | 0.0 (6) |
N4—N5—C26—S3 | 0.6 (4) | O1—C15—C16—C17 | 59.5 (5) |
N4—N5—C26—C27 | 179.6 (3) | C15—C16—C17—N3 | −173.0 (4) |
C30—N6—C22—C21 | −133.6 (4) | S1—C20—C21—C22 | 19.2 (5) |
C30—N6—C22—C23 | 49.7 (5) | S1—C20—C21—C24 | −163.3 (2) |
C28—N6—C22—C23 | −167.3 (3) | C20—C21—C22—N6 | 6.9 (5) |
C30—N6—C28—C29 | −11.3 (3) | C20—C21—C22—C23 | −176.7 (3) |
C22—N6—C28—S1 | −48.2 (4) | C20—C21—C24—S2 | 81.3 (3) |
C22—N6—C28—C29 | −165.4 (3) | C22—C21—C24—S2 | −101.2 (4) |
C22—N6—C30—O4 | −16.5 (7) | C24—C21—C22—N6 | −170.3 (3) |
C28—N6—C22—C21 | 9.4 (5) | C24—C21—C22—C23 | 6.0 (6) |
C30—N6—C28—S1 | 106.0 (2) | N6—C22—C23—O2 | 32.8 (5) |
C22—N6—C30—C29 | 161.9 (4) | C21—C22—C23—O3 | 37.0 (5) |
C28—N6—C30—O4 | −167.1 (4) | N6—C22—C23—O3 | −146.5 (3) |
C28—N6—C30—C29 | 11.3 (3) | C21—C22—C23—O2 | −143.7 (4) |
C29—N7—C31—O5 | −1.4 (5) | S1—C28—C29—N7 | 21.1 (4) |
C31—N7—C29—C30 | −145.3 (3) | S1—C28—C29—C30 | −100.9 (3) |
C29—N7—C31—C32 | 176.6 (3) | N6—C28—C29—N7 | 132.1 (3) |
C31—N7—C29—C28 | 111.5 (4) | N6—C28—C29—C30 | 10.1 (2) |
N9—N8—C32—C31 | −69.8 (4) | N7—C29—C30—O4 | 44.4 (6) |
N9—N8—C33—N11 | −0.1 (4) | N7—C29—C30—N6 | −133.9 (3) |
C32—N8—C33—N11 | −177.9 (3) | C28—C29—C30—O4 | 167.5 (5) |
C33—N8—N9—N10 | 0.0 (4) | C28—C29—C30—N6 | −10.7 (3) |
C32—N8—N9—N10 | 178.1 (4) | O5—C31—C32—N8 | −38.1 (5) |
C33—N8—C32—C31 | 107.8 (4) | N7—C31—C32—N8 | 143.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O3i | 0.96 (4) | 1.70 (4) | 2.660 (4) | 174 (3) |
N7—H7N···O2ii | 0.8600 | 2.0200 | 2.868 (3) | 167.00 |
C18—H18C···O4iii | 0.9600 | 2.5200 | 3.303 (5) | 139.00 |
C24—H24A···N4 | 0.9700 | 2.4100 | 2.961 (5) | 116.00 |
C24—H24B···O3 | 0.9700 | 2.3800 | 2.882 (4) | 112.00 |
C32—H32A···O2iv | 0.9700 | 2.2800 | 3.218 (4) | 164.00 |
C32—H32B···O2ii | 0.9700 | 2.5000 | 3.318 (4) | 142.00 |
C19—H19B···CgA | 0.96 | 2.91 | 3.869 (6) | 174 |
C20—H20B···CgD | 0.97 | 2.72 | 3.642 (4) | 158 |
C29—H29···CgAii | 0.98 | 2.99 | 3.861 (4) | 149 |
Symmetry codes: (i) x, y−1, z+1; (ii) x, y−1, z; (iii) x, y, z+1; (iv) −x, y−1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H24N3O+·C14H13N8O4S3− |
Mr | 763.92 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 296 |
a, b, c (Å) | 44.409 (3), 7.1777 (5), 11.2683 (8) |
β (°) | 90.587 (8) |
V (Å3) | 3591.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.24 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.957, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34321, 6750, 4092 |
Rint | 0.088 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.095, 1.00 |
No. of reflections | 6750 |
No. of parameters | 475 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.23 |
Absolute structure | Flack (1983), 2918 Friedal Pairs |
Absolute structure parameter | −0.07 (7) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O3i | 0.96 (4) | 1.70 (4) | 2.660 (4) | 174 (3) |
N7—H7N···O2ii | 0.8600 | 2.0200 | 2.868 (3) | 167.00 |
C18—H18C···O4iii | 0.9600 | 2.5200 | 3.303 (5) | 139.00 |
C24—H24A···N4 | 0.9700 | 2.4100 | 2.961 (5) | 116.00 |
C24—H24B···O3 | 0.9700 | 2.3800 | 2.882 (4) | 112.00 |
C32—H32A···O2iv | 0.9700 | 2.2800 | 3.218 (4) | 164.00 |
C32—H32B···O2ii | 0.9700 | 2.5000 | 3.318 (4) | 142.00 |
C19—H19B···CgA | 0.96 | 2.91 | 3.869 (6) | 174 |
C20—H20B···CgD | 0.97 | 2.72 | 3.642 (4) | 158 |
C29—H29···CgAii | 0.98 | 2.99 | 3.861 (4) | 149 |
Symmetry codes: (i) x, y−1, z+1; (ii) x, y−1, z; (iii) x, y, z+1; (iv) −x, y−1, −z+1. |
Acknowledgements
AA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a Scholaship under the Indigenous PhD Program.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
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Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
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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.
Cephazolin, is a first generation cefalosporin antibiotic and benzydamin hydrochloride is a locally acting nonsteroidal anti-inflammatory drug with local anaesthetic and analgesic properties providing both rapid and extended pain relief as well as a significant anti-inflammatory treatment for the painful inflammatory conditions of mouth and throat (Turnbull, 1995). The title compound (I, Fig. 1) was prepared as a mutual prodrug for the treatment of infections and inflamatory conditions.
No crystal structure has been found related to cation. In the cation the indazol moiety A (C1–C6/N2/N1/C14) and the benzene ring B (C8–C13) are planar with r.m.s. deviations of 0.0258 and 0.0031 Å respectively, from the respective mean square planes. The dihedral angle between A/B is 71.06 (12)°. In this cation, there exist an intramolecular H-bonding of C—H···O type (Table 1, Fig. 1) forming S(5) ring motif (Bernstein et al., 1995) in the envelop form.
In the anion, two five membered heterocyclic rings C (C25/S3/C26/N5/N4) and D (N8—N9/C33) are planar with r. m. s. deviations of 0.0025 and 0.0014 Å respectively, from the respective mean square planes and the dihedral angle between C/D is 38.58 (14)°. The heterocyclic six membered E (C20/C21/C22/N6/C28/S1) is in the twisted form, with the maximum puckering amplitude QT = 0.623 (4) Å (Cremer & Pople, 1975) and the four membered ring F (N6/C28–C30) is not planar also. In anion, there exist two S(5) and a S(6) ring motifs (Table 1, Fig. 1). The molecules are stabilized in the form of polymeric chains forming R21(6), R42(8), R22(10) and other ring motifs (Fig. 2 & Fig. 3).