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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-Benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com

(Received 2 July 2012; accepted 2 July 2012; online 7 July 2012)

The title mol­ecule, C24H15NO4, crystallizes with two mol­ecules in the asymmetric unit (Z′ = 2). For both mol­ecules, the two amide groups are not coplanar, as the dihedral angles of the respective NCO groups are similar at 50.37 (14) and 51.22 (13)°. However, the orientations of the substituent phenyl rings with the central naphthalene system are significantly different for the two mol­ecules; for one mol­ecule, these dihedral angles are 80.29 (3) and 80.95 (4)°, while for the second mol­ecule they are 86.63 (3) and 72.82 (4)°. The crystal packing shows the mol­ecules to be linked by weak C—H⋯O inter­actions.

Related literature

For related structures, see: Akinboye, Butcher, Brandy et al. (2009[Akinboye, E. S., Butcher, R. J., Brandy, Y., Adesiyun, T. A. & Bakare, O. (2009). Acta Cryst. E65, o24.]); Akinboye, Butcher, Wright et al. (2009[Akinboye, E. S., Butcher, R. J., Wright, D. A., Brandy, Y. & Bakare, O. (2009). Acta Cryst. E65, o277.]). For pharmacological properties of related compounds, see: Bakare et al. (2003[Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165-3170.]); Khraiwesh et al. (2011[Khraiwesh, H. M., Lee, C. M., Brandy, Y., Akinboye, E. S., Berhe, S., Gittens, G., Abbas, M. M., Ampy, F. R., Ashraf, M. & Bakare, O. (2011). Arch. Pharm. Res. 35, 27-33.]); Berhe et al. (2008[Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug Des. Discov. 5, 485-488.]).

[Scheme 1]

Experimental

Crystal data
  • C24H15NO4

  • Mr = 381.37

  • Triclinic, [P \overline 1]

  • a = 9.8704 (11) Å

  • b = 12.6776 (11) Å

  • c = 15.6472 (14) Å

  • α = 90.735 (7)°

  • β = 98.213 (9)°

  • γ = 108.187 (9)°

  • V = 1837.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 123 K

  • 0.52 × 0.28 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.751, Tmax = 1.000

  • 26547 measured reflections

  • 26547 independent reflections

  • 17970 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.221

  • S = 1.03

  • 26547 reflections

  • 524 parameters

  • H-atom parameters constrained

  • Δρmax = 0.70 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C21A—H21A⋯O2Bi 0.95 2.41 3.1270 (19) 132
C14B—H14B⋯O3Aii 0.95 2.50 3.4345 (17) 168
C15B—H15B⋯O4Aiii 0.95 2.62 3.4638 (17) 148
C22B—H22B⋯O2A 0.95 2.54 3.2054 (17) 127
C14A—H14A⋯O3B 0.95 2.44 3.2303 (16) 140
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

We have previously synthesized some cyclic and acyclic imido-3-chloro-naphthoquinone analogs and studied their anticancer activities against some prostate cancer cell lines (Bakare et al. (2003); Berhe et al. (2008)). In addition, some aryl imido -2-chloro and -2-bromo-1,4-naphthoquinone analogs were synthesized and some crystal structures were already reported for the 2-N-bis(2-chlorobenzoyl)amino and 2-N-bis(4-fluorobenzoyl) amino-3-bromo-1,4-naphthoquinone derivatives (Akinboye, Butcher, Brandy et al. (2009); Akinboye, Butcher, Wright et al. (2009)). Recently, we have reported some antiparasitic studies of some of the aryl imidonaphthoquinones (Khraiwesh, et al., (2011)) and are currently studying their anticancer properties against PC3 prostate cancer cells. In continuation of our work, N-benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide was synthesized as a potential antiprostate cancer agent and its structure is reported here.

In the structure of the title compound there are two molecules in the asymmetric unit (Z' = 2). For both molecules the two amide moieties are not coplanar as the dihedral angles of the respective NCO groups are similar at 50.37 (14)° and 51.22 (13)°). However, the orientations of the substituent phenyl rings with the central naphthyl ring are significantly different for the two molecules. For molecule A these dihedral angles are 80.29 (3)° and 80.95 (4)° between the naphthyl ring and rings C12 - C17 and C19 - C24, while for molecule B these values are 86.63 (3)° and 72.82 (4)°.

In the two molecules the imide C=O's are at dihedral angles of 42.95 (17)° and -121.12 (13)° for molecule A and -44.89 (17)° and 121.05 (13)° for molecule B and are thus anti to each other. The anti conformation of these imide C=O's and the dihedral angles between the phenyl rings and imide C=O groups oriented the phenyl groups away from each other (values of (34.2 (2)° and 25.29 (18)°) for A and -24.03 (17) and -42.44 (19)° for B). The crystal structure packing pattern shows the molecules were linked by weak intermolecular C—H···O interactions.

Related literature top

For related structures, see: Akinboye, Butcher, Brandy et al. (2009); Akinboye, Butcher, Wright et al. (2009). For pharmacological properties of related compounds, see: Bakare et al. (2003); Khraiwesh et al. (2011); Berhe et al. (2008).

Experimental top

2-Amino-1,4-naphthoquinone (318 mg, 1.83 mmol) was dissolved in freshly distilled THF (15 ml). NaH (115 mg, 4.78 mmol) was added and the mixture was stirred at room temperature for 15 min. The appropriate benzoyl chloride (0.55 ml, 4.74 mmol) was added, drop wise, and the mixture was stirred for 24 h. THF was evaporated under vacuum and the mixture was washed with ice-water (10 g ice in 10 ml water). The aqueous mixture was extracted with CH2Cl2 (30 ml, 20 ml consecutively) and the combined organic phase washed with water (3 x 20 ml), saturated NaCl solution (20 ml), then dried over anhydrous MgSO4. The crude was purified via tirturating in ethanol (2 ml) and column chromatography with an eluent mixture of ethyl acetate and hexane to furnish the imide(70 mg, 10%).

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distance of 0.95 and Uiso(H) = 1.2Ueq(C). The structure was a non-merohedral twin and was refined with a BASF (batch scale factor) value of 0.4084 (7) and a twin law for the two components of -1 0 0, 0 - 1 0, 0 0 1.

Structure description top

We have previously synthesized some cyclic and acyclic imido-3-chloro-naphthoquinone analogs and studied their anticancer activities against some prostate cancer cell lines (Bakare et al. (2003); Berhe et al. (2008)). In addition, some aryl imido -2-chloro and -2-bromo-1,4-naphthoquinone analogs were synthesized and some crystal structures were already reported for the 2-N-bis(2-chlorobenzoyl)amino and 2-N-bis(4-fluorobenzoyl) amino-3-bromo-1,4-naphthoquinone derivatives (Akinboye, Butcher, Brandy et al. (2009); Akinboye, Butcher, Wright et al. (2009)). Recently, we have reported some antiparasitic studies of some of the aryl imidonaphthoquinones (Khraiwesh, et al., (2011)) and are currently studying their anticancer properties against PC3 prostate cancer cells. In continuation of our work, N-benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide was synthesized as a potential antiprostate cancer agent and its structure is reported here.

In the structure of the title compound there are two molecules in the asymmetric unit (Z' = 2). For both molecules the two amide moieties are not coplanar as the dihedral angles of the respective NCO groups are similar at 50.37 (14)° and 51.22 (13)°). However, the orientations of the substituent phenyl rings with the central naphthyl ring are significantly different for the two molecules. For molecule A these dihedral angles are 80.29 (3)° and 80.95 (4)° between the naphthyl ring and rings C12 - C17 and C19 - C24, while for molecule B these values are 86.63 (3)° and 72.82 (4)°.

In the two molecules the imide C=O's are at dihedral angles of 42.95 (17)° and -121.12 (13)° for molecule A and -44.89 (17)° and 121.05 (13)° for molecule B and are thus anti to each other. The anti conformation of these imide C=O's and the dihedral angles between the phenyl rings and imide C=O groups oriented the phenyl groups away from each other (values of (34.2 (2)° and 25.29 (18)°) for A and -24.03 (17) and -42.44 (19)° for B). The crystal structure packing pattern shows the molecules were linked by weak intermolecular C—H···O interactions.

For related structures, see: Akinboye, Butcher, Brandy et al. (2009); Akinboye, Butcher, Wright et al. (2009). For pharmacological properties of related compounds, see: Bakare et al. (2003); Khraiwesh et al. (2011); Berhe et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Diagram of C24H15NO4 showing the atom labeling for the two molecules in the asymmetric unit. The C—H···O interactions are shown by dashed lines. Thermal ellipsoids are at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing for C24H15NO4 viewed along the a axis. The C—H···O interactions are shown by dashed lines.
N-Benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide top
Crystal data top
C24H15NO4Z = 4
Mr = 381.37F(000) = 792
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8704 (11) ÅCell parameters from 3142 reflections
b = 12.6776 (11) Åθ = 3.0–34.9°
c = 15.6472 (14) ŵ = 0.10 mm1
α = 90.735 (7)°T = 123 K
β = 98.213 (9)°Block, colorless
γ = 108.187 (9)°0.52 × 0.28 × 0.15 mm
V = 1837.6 (3) Å3
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
26547 independent reflections
Radiation source: Enhance (Mo) X-ray Source17970 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.0000
Detector resolution: 10.5081 pixels mm-1θmax = 35.2°, θmin = 3.1°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
k = 2020
Tmin = 0.751, Tmax = 1.000l = 2421
26547 measured reflections
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) = 0.221H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1412P)2]
where P = (Fo2 + 2Fc2)/3
26547 reflections(Δ/σ)max = 0.001
524 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C24H15NO4γ = 108.187 (9)°
Mr = 381.37V = 1837.6 (3) Å3
Triclinic, P1Z = 4
a = 9.8704 (11) ÅMo Kα radiation
b = 12.6776 (11) ŵ = 0.10 mm1
c = 15.6472 (14) ÅT = 123 K
α = 90.735 (7)°0.52 × 0.28 × 0.15 mm
β = 98.213 (9)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
26547 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
17970 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 1.000Rint = 0.0000
26547 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.221H-atom parameters constrained
S = 1.03Δρmax = 0.70 e Å3
26547 reflectionsΔρmin = 0.43 e Å3
524 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.61934 (11)0.65075 (8)1.11669 (6)0.0244 (2)
O2A0.15230 (10)0.64038 (8)0.89442 (6)0.02104 (19)
O3A0.50651 (10)1.01393 (8)0.90297 (6)0.02088 (19)
O4A0.18605 (11)0.84042 (8)1.00964 (6)0.02152 (19)
N1A0.36272 (12)0.84143 (9)0.93028 (7)0.0166 (2)
C1A0.37834 (13)0.74566 (10)0.97147 (7)0.0153 (2)
C2A0.49758 (14)0.74697 (10)1.02443 (8)0.0173 (2)
H2AA0.57670.81391.03420.021*
C3A0.50990 (14)0.64715 (10)1.06827 (8)0.0173 (2)
C4A0.38274 (13)0.54455 (10)1.05355 (7)0.0160 (2)
C5A0.38512 (15)0.45054 (11)1.09716 (9)0.0209 (2)
H5AA0.46860.45151.13620.025*
C6A0.26582 (16)0.35463 (11)1.08401 (9)0.0240 (3)
H6AA0.26850.29021.11370.029*
C7A0.14371 (16)0.35298 (11)1.02791 (9)0.0230 (3)
H7AA0.06200.28771.01950.028*
C8A0.14043 (15)0.44648 (11)0.98398 (8)0.0198 (2)
H8AA0.05670.44500.94490.024*
C9A0.25916 (14)0.54244 (10)0.99677 (7)0.0158 (2)
C10A0.25331 (13)0.64191 (10)0.94990 (7)0.0155 (2)
C11A0.47714 (14)0.91402 (10)0.89268 (7)0.0165 (2)
C12A0.55113 (14)0.86068 (10)0.83735 (8)0.0166 (2)
C13A0.47877 (15)0.75844 (11)0.79278 (8)0.0187 (2)
H13A0.38350.71840.80170.022*
C14A0.54511 (16)0.71467 (12)0.73529 (8)0.0226 (3)
H14A0.49520.64500.70460.027*
C15A0.68457 (17)0.77295 (13)0.72280 (8)0.0251 (3)
H15A0.73070.74290.68400.030*
C16A0.75694 (16)0.87551 (13)0.76714 (9)0.0253 (3)
H16A0.85250.91520.75850.030*
C17A0.69028 (15)0.92022 (11)0.82395 (8)0.0207 (2)
H17A0.73920.99080.85340.025*
C18A0.24559 (14)0.87524 (10)0.94867 (8)0.0169 (2)
C19A0.19812 (14)0.95011 (11)0.88779 (9)0.0206 (2)
C20A0.20504 (17)0.94166 (13)0.79946 (9)0.0271 (3)
H20A0.24130.88760.77710.033*
C21A0.15885 (19)1.01249 (15)0.74495 (11)0.0367 (4)
H21A0.16231.00660.68480.044*
C22A0.10775 (19)1.09162 (14)0.77739 (13)0.0410 (4)
H22A0.07911.14150.73970.049*
C23A0.09770 (19)1.09917 (14)0.86423 (13)0.0389 (4)
H23A0.06091.15320.88600.047*
C24A0.14178 (16)1.02722 (12)0.91974 (10)0.0268 (3)
H24A0.13331.03090.97930.032*
O1B0.60121 (11)0.13107 (9)0.39332 (6)0.0239 (2)
O2B0.18809 (11)0.14122 (8)0.57590 (6)0.02112 (19)
O3B0.53144 (11)0.51594 (8)0.59971 (6)0.01961 (18)
O4B0.18878 (11)0.32712 (8)0.45919 (6)0.0232 (2)
N1B0.38724 (11)0.33871 (9)0.55734 (6)0.01598 (19)
C1B0.39502 (13)0.23977 (10)0.51787 (7)0.0149 (2)
C2B0.50258 (14)0.23682 (11)0.47547 (8)0.0181 (2)
H2BA0.58090.30290.47380.022*
C3B0.50210 (14)0.13280 (11)0.43110 (8)0.0176 (2)
C4B0.37397 (14)0.03230 (10)0.43147 (7)0.0170 (2)
C5B0.36221 (16)0.06502 (11)0.38440 (8)0.0216 (3)
H5BA0.43530.06700.35150.026*
C6B0.24392 (16)0.15902 (12)0.38559 (9)0.0248 (3)
H6BA0.23560.22490.35280.030*
C7B0.13726 (15)0.15763 (11)0.43448 (9)0.0242 (3)
H7BA0.05700.22260.43540.029*
C8B0.14839 (15)0.06103 (11)0.48195 (9)0.0215 (2)
H8BA0.07640.06000.51600.026*
C9B0.26546 (13)0.03420 (10)0.47945 (8)0.0163 (2)
C10B0.27458 (13)0.13758 (10)0.52801 (7)0.0157 (2)
C11B0.50716 (13)0.41715 (10)0.60839 (7)0.0155 (2)
C12B0.59360 (13)0.37346 (10)0.67570 (7)0.0164 (2)
C13B0.53263 (14)0.27461 (11)0.71402 (8)0.0179 (2)
H13B0.43630.22970.69320.021*
C14B0.61293 (16)0.24183 (12)0.78280 (8)0.0226 (3)
H14B0.57230.17420.80880.027*
C15B0.75295 (17)0.30876 (13)0.81313 (8)0.0258 (3)
H15B0.80810.28660.86010.031*
C16B0.81343 (16)0.40773 (13)0.77565 (8)0.0247 (3)
H16B0.90950.45290.79680.030*
C17B0.73313 (14)0.44047 (11)0.70715 (8)0.0199 (2)
H17B0.77360.50870.68180.024*
C18B0.26274 (14)0.36802 (10)0.52716 (8)0.0174 (2)
C19B0.22434 (13)0.44303 (10)0.58654 (8)0.0176 (2)
C20B0.23316 (15)0.42713 (11)0.67508 (8)0.0211 (2)
H20B0.27010.37130.69900.025*
C21B0.18735 (16)0.49364 (13)0.72766 (9)0.0251 (3)
H21B0.19180.48260.78780.030*
C22B0.13520 (16)0.57591 (13)0.69353 (10)0.0266 (3)
H22B0.10490.62150.73030.032*
C23B0.12693 (16)0.59214 (12)0.60551 (10)0.0257 (3)
H23B0.09230.64930.58210.031*
C24B0.16968 (15)0.52406 (11)0.55198 (9)0.0215 (3)
H24B0.16130.53320.49150.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0214 (5)0.0244 (5)0.0260 (5)0.0075 (4)0.0014 (4)0.0038 (4)
O2A0.0221 (5)0.0188 (4)0.0199 (4)0.0053 (4)0.0014 (3)0.0022 (3)
O3A0.0260 (5)0.0144 (4)0.0220 (4)0.0050 (4)0.0060 (4)0.0017 (3)
O4A0.0227 (5)0.0232 (5)0.0195 (4)0.0068 (4)0.0074 (3)0.0027 (4)
N1A0.0217 (5)0.0134 (4)0.0162 (4)0.0065 (4)0.0057 (4)0.0035 (4)
C1A0.0192 (6)0.0133 (5)0.0144 (5)0.0052 (4)0.0049 (4)0.0027 (4)
C2A0.0181 (6)0.0146 (5)0.0184 (5)0.0036 (4)0.0038 (4)0.0004 (4)
C3A0.0185 (6)0.0174 (5)0.0163 (5)0.0056 (4)0.0034 (4)0.0007 (4)
C4A0.0178 (5)0.0156 (5)0.0154 (5)0.0060 (4)0.0041 (4)0.0022 (4)
C5A0.0237 (6)0.0189 (6)0.0217 (6)0.0089 (5)0.0033 (5)0.0047 (5)
C6A0.0289 (7)0.0163 (6)0.0272 (6)0.0067 (5)0.0062 (5)0.0085 (5)
C7A0.0245 (7)0.0149 (5)0.0287 (7)0.0036 (5)0.0074 (5)0.0034 (5)
C8A0.0197 (6)0.0171 (5)0.0219 (6)0.0054 (5)0.0025 (4)0.0007 (4)
C9A0.0191 (6)0.0141 (5)0.0151 (5)0.0060 (4)0.0040 (4)0.0011 (4)
C10A0.0193 (6)0.0139 (5)0.0140 (5)0.0060 (4)0.0035 (4)0.0007 (4)
C11A0.0196 (6)0.0161 (5)0.0134 (5)0.0052 (4)0.0027 (4)0.0022 (4)
C12A0.0211 (6)0.0157 (5)0.0142 (5)0.0069 (4)0.0042 (4)0.0027 (4)
C13A0.0243 (6)0.0175 (5)0.0153 (5)0.0073 (5)0.0044 (4)0.0017 (4)
C14A0.0323 (7)0.0227 (6)0.0156 (5)0.0127 (5)0.0037 (5)0.0005 (5)
C15A0.0330 (8)0.0327 (7)0.0180 (6)0.0197 (6)0.0094 (5)0.0056 (5)
C16A0.0239 (7)0.0294 (7)0.0258 (6)0.0100 (6)0.0106 (5)0.0083 (5)
C17A0.0222 (6)0.0197 (6)0.0205 (6)0.0054 (5)0.0064 (5)0.0051 (5)
C18A0.0198 (6)0.0138 (5)0.0170 (5)0.0054 (4)0.0025 (4)0.0001 (4)
C19A0.0194 (6)0.0186 (6)0.0239 (6)0.0067 (5)0.0023 (5)0.0040 (5)
C20A0.0285 (7)0.0295 (7)0.0232 (6)0.0092 (6)0.0032 (5)0.0074 (5)
C21A0.0333 (9)0.0418 (9)0.0315 (8)0.0086 (7)0.0001 (6)0.0172 (7)
C22A0.0337 (9)0.0283 (8)0.0546 (11)0.0075 (7)0.0095 (8)0.0182 (8)
C23A0.0348 (9)0.0237 (7)0.0571 (11)0.0149 (7)0.0085 (8)0.0021 (7)
C24A0.0244 (7)0.0212 (6)0.0355 (7)0.0105 (5)0.0001 (6)0.0019 (6)
O1B0.0253 (5)0.0267 (5)0.0251 (5)0.0130 (4)0.0103 (4)0.0033 (4)
O2B0.0216 (5)0.0201 (4)0.0223 (4)0.0056 (4)0.0079 (4)0.0004 (4)
O3B0.0238 (5)0.0150 (4)0.0200 (4)0.0059 (3)0.0039 (3)0.0006 (3)
O4B0.0240 (5)0.0264 (5)0.0197 (4)0.0112 (4)0.0021 (4)0.0034 (4)
N1B0.0171 (5)0.0149 (5)0.0164 (4)0.0062 (4)0.0018 (4)0.0007 (4)
C1B0.0176 (5)0.0134 (5)0.0146 (5)0.0066 (4)0.0015 (4)0.0004 (4)
C2B0.0198 (6)0.0179 (5)0.0178 (5)0.0070 (5)0.0047 (4)0.0020 (4)
C3B0.0201 (6)0.0198 (6)0.0161 (5)0.0104 (5)0.0038 (4)0.0029 (4)
C4B0.0213 (6)0.0180 (5)0.0144 (5)0.0105 (5)0.0012 (4)0.0011 (4)
C5B0.0271 (7)0.0208 (6)0.0199 (6)0.0125 (5)0.0025 (5)0.0024 (5)
C6B0.0307 (7)0.0189 (6)0.0258 (6)0.0116 (5)0.0004 (5)0.0050 (5)
C7B0.0218 (6)0.0157 (6)0.0317 (7)0.0040 (5)0.0021 (5)0.0029 (5)
C8B0.0191 (6)0.0183 (6)0.0269 (6)0.0066 (5)0.0017 (5)0.0015 (5)
C9B0.0177 (6)0.0153 (5)0.0169 (5)0.0073 (4)0.0007 (4)0.0002 (4)
C10B0.0166 (5)0.0154 (5)0.0157 (5)0.0061 (4)0.0017 (4)0.0004 (4)
C11B0.0172 (5)0.0167 (5)0.0137 (5)0.0063 (4)0.0035 (4)0.0001 (4)
C12B0.0183 (6)0.0184 (5)0.0137 (5)0.0073 (4)0.0029 (4)0.0001 (4)
C13B0.0212 (6)0.0170 (5)0.0157 (5)0.0057 (4)0.0042 (4)0.0007 (4)
C14B0.0344 (7)0.0233 (6)0.0149 (5)0.0148 (6)0.0066 (5)0.0034 (5)
C15B0.0326 (8)0.0350 (8)0.0153 (5)0.0194 (6)0.0017 (5)0.0035 (5)
C16B0.0233 (7)0.0324 (7)0.0184 (6)0.0104 (6)0.0000 (5)0.0013 (5)
C17B0.0203 (6)0.0216 (6)0.0171 (5)0.0063 (5)0.0018 (4)0.0000 (4)
C18B0.0172 (6)0.0171 (5)0.0192 (5)0.0073 (4)0.0025 (4)0.0017 (4)
C19B0.0159 (5)0.0179 (5)0.0200 (5)0.0065 (4)0.0029 (4)0.0016 (4)
C20B0.0207 (6)0.0225 (6)0.0212 (6)0.0079 (5)0.0047 (5)0.0007 (5)
C21B0.0239 (7)0.0299 (7)0.0228 (6)0.0088 (6)0.0071 (5)0.0020 (5)
C22B0.0228 (7)0.0274 (7)0.0308 (7)0.0103 (5)0.0045 (5)0.0098 (6)
C23B0.0243 (7)0.0239 (7)0.0314 (7)0.0134 (5)0.0001 (5)0.0030 (5)
C24B0.0198 (6)0.0228 (6)0.0229 (6)0.0097 (5)0.0001 (5)0.0003 (5)
Geometric parameters (Å, º) top
O1A—C3A1.2154 (16)O1B—C3B1.2188 (15)
O2A—C10A1.2199 (15)O2B—C10B1.2243 (15)
O3A—C11A1.2109 (15)O3B—C11B1.2127 (15)
O4A—C18A1.2080 (15)O4B—C18B1.2086 (15)
N1A—C18A1.4158 (16)N1B—C18B1.4125 (16)
N1A—C1A1.4218 (15)N1B—C11B1.4152 (16)
N1A—C11A1.4226 (16)N1B—C1B1.4192 (15)
C1A—C2A1.3345 (17)C1B—C2B1.3395 (17)
C1A—C10A1.4911 (18)C1B—C10B1.4882 (17)
C2A—C3A1.4769 (18)C2B—C3B1.4807 (17)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.4869 (18)C3B—C4B1.4897 (19)
C4A—C5A1.3858 (17)C4B—C5B1.3933 (17)
C4A—C9A1.3955 (17)C4B—C9B1.3988 (17)
C5A—C6A1.392 (2)C5B—C6B1.386 (2)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.380 (2)C6B—C7B1.391 (2)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.3846 (18)C7B—C8B1.3903 (18)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.3893 (18)C8B—C9B1.3920 (18)
C8A—H8AA0.9500C8B—H8BA0.9500
C9A—C10A1.4793 (17)C9B—C10B1.4780 (16)
C11A—C12A1.4880 (17)C11B—C12B1.4824 (17)
C12A—C13A1.3904 (18)C12B—C17B1.3877 (18)
C12A—C17A1.3926 (18)C12B—C13B1.3942 (18)
C13A—C14A1.3886 (18)C13B—C14B1.3901 (18)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.387 (2)C14B—C15B1.388 (2)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.392 (2)C15B—C16B1.388 (2)
C15A—H15A0.9500C15B—H15B0.9500
C16A—C17A1.3897 (18)C16B—C17B1.3869 (18)
C16A—H16A0.9500C16B—H16B0.9500
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.4836 (18)C18B—C19B1.4881 (17)
C19A—C24A1.3860 (19)C19B—C24B1.3841 (18)
C19A—C20A1.398 (2)C19B—C20B1.3967 (18)
C20A—C21A1.380 (2)C20B—C21B1.3852 (18)
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.376 (3)C21B—C22B1.382 (2)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.381 (3)C22B—C23B1.390 (2)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.391 (2)C23B—C24B1.3907 (19)
C23A—H23A0.9500C23B—H23B0.9500
C24A—H24A0.9500C24B—H24B0.9500
C18A—N1A—C1A115.64 (10)C18B—N1B—C11B119.88 (10)
C18A—N1A—C11A121.20 (10)C18B—N1B—C1B115.62 (10)
C1A—N1A—C11A121.16 (11)C11B—N1B—C1B123.00 (10)
C2A—C1A—N1A122.76 (11)C2B—C1B—N1B123.34 (11)
C2A—C1A—C10A121.76 (11)C2B—C1B—C10B121.83 (11)
N1A—C1A—C10A115.46 (11)N1B—C1B—C10B114.83 (10)
C1A—C2A—C3A121.80 (11)C1B—C2B—C3B121.46 (12)
C1A—C2A—H2AA119.1C1B—C2B—H2BA119.3
C3A—C2A—H2AA119.1C3B—C2B—H2BA119.3
O1A—C3A—C2A120.50 (12)O1B—C3B—C2B120.78 (12)
O1A—C3A—C4A121.68 (12)O1B—C3B—C4B121.54 (12)
C2A—C3A—C4A117.79 (11)C2B—C3B—C4B117.63 (11)
C5A—C4A—C9A119.36 (12)C5B—C4B—C9B119.45 (12)
C5A—C4A—C3A120.22 (11)C5B—C4B—C3B119.95 (12)
C9A—C4A—C3A120.41 (11)C9B—C4B—C3B120.60 (11)
C4A—C5A—C6A120.35 (13)C6B—C5B—C4B120.00 (13)
C4A—C5A—H5AA119.8C6B—C5B—H5BA120.0
C6A—C5A—H5AA119.8C4B—C5B—H5BA120.0
C7A—C6A—C5A120.09 (12)C5B—C6B—C7B120.52 (12)
C7A—C6A—H6AA120.0C5B—C6B—H6BA119.7
C5A—C6A—H6AA120.0C7B—C6B—H6BA119.7
C6A—C7A—C8A119.95 (13)C8B—C7B—C6B119.88 (13)
C6A—C7A—H7AA120.0C8B—C7B—H7BA120.1
C8A—C7A—H7AA120.0C6B—C7B—H7BA120.1
C7A—C8A—C9A120.24 (13)C7B—C8B—C9B119.75 (13)
C7A—C8A—H8AA119.9C7B—C8B—H8BA120.1
C9A—C8A—H8AA119.9C9B—C8B—H8BA120.1
C8A—C9A—C4A120.00 (11)C8B—C9B—C4B120.37 (11)
C8A—C9A—C10A119.53 (11)C8B—C9B—C10B119.53 (11)
C4A—C9A—C10A120.48 (11)C4B—C9B—C10B120.10 (11)
O2A—C10A—C9A122.29 (11)O2B—C10B—C9B122.45 (11)
O2A—C10A—C1A120.24 (11)O2B—C10B—C1B119.78 (11)
C9A—C10A—C1A117.45 (11)C9B—C10B—C1B117.77 (11)
O3A—C11A—N1A120.52 (11)O3B—C11B—N1B120.39 (11)
O3A—C11A—C12A122.84 (12)O3B—C11B—C12B122.35 (11)
N1A—C11A—C12A116.56 (11)N1B—C11B—C12B117.14 (11)
C13A—C12A—C17A120.08 (12)C17B—C12B—C13B120.25 (12)
C13A—C12A—C11A121.06 (12)C17B—C12B—C11B117.80 (12)
C17A—C12A—C11A118.55 (12)C13B—C12B—C11B121.52 (11)
C14A—C13A—C12A120.29 (13)C14B—C13B—C12B119.90 (13)
C14A—C13A—H13A119.9C14B—C13B—H13B120.1
C12A—C13A—H13A119.9C12B—C13B—H13B120.1
C15A—C14A—C13A119.78 (13)C15B—C14B—C13B119.42 (13)
C15A—C14A—H14A120.1C15B—C14B—H14B120.3
C13A—C14A—H14A120.1C13B—C14B—H14B120.3
C14A—C15A—C16A119.99 (12)C14B—C15B—C16B120.80 (13)
C14A—C15A—H15A120.0C14B—C15B—H15B119.6
C16A—C15A—H15A120.0C16B—C15B—H15B119.6
C17A—C16A—C15A120.40 (13)C17B—C16B—C15B119.74 (14)
C17A—C16A—H16A119.8C17B—C16B—H16B120.1
C15A—C16A—H16A119.8C15B—C16B—H16B120.1
C16A—C17A—C12A119.45 (13)C16B—C17B—C12B119.88 (13)
C16A—C17A—H17A120.3C16B—C17B—H17B120.1
C12A—C17A—H17A120.3C12B—C17B—H17B120.1
O4A—C18A—N1A120.27 (11)O4B—C18B—N1B120.19 (11)
O4A—C18A—C19A123.00 (12)O4B—C18B—C19B123.43 (12)
N1A—C18A—C19A116.68 (11)N1B—C18B—C19B116.20 (11)
C24A—C19A—C20A120.03 (13)C24B—C19B—C20B120.16 (12)
C24A—C19A—C18A118.57 (12)C24B—C19B—C18B118.96 (11)
C20A—C19A—C18A121.36 (12)C20B—C19B—C18B120.72 (11)
C21A—C20A—C19A119.50 (15)C21B—C20B—C19B119.25 (13)
C21A—C20A—H20A120.3C21B—C20B—H20B120.4
C19A—C20A—H20A120.3C19B—C20B—H20B120.4
C22A—C21A—C20A120.30 (16)C22B—C21B—C20B120.66 (13)
C22A—C21A—H21A119.8C22B—C21B—H21B119.7
C20A—C21A—H21A119.8C20B—C21B—H21B119.7
C21A—C22A—C23A120.65 (15)C21B—C22B—C23B120.15 (13)
C21A—C22A—H22A119.7C21B—C22B—H22B119.9
C23A—C22A—H22A119.7C23B—C22B—H22B119.9
C22A—C23A—C24A119.68 (16)C22B—C23B—C24B119.52 (13)
C22A—C23A—H23A120.2C22B—C23B—H23B120.2
C24A—C23A—H23A120.2C24B—C23B—H23B120.2
C19A—C24A—C23A119.77 (15)C19B—C24B—C23B120.22 (13)
C19A—C24A—H24A120.1C19B—C24B—H24B119.9
C23A—C24A—H24A120.1C23B—C24B—H24B119.9
C18A—N1A—C1A—C2A121.12 (13)C18B—N1B—C1B—C2B121.05 (13)
C11A—N1A—C1A—C2A42.95 (17)C11B—N1B—C1B—C2B44.89 (17)
C18A—N1A—C1A—C10A60.33 (14)C18B—N1B—C1B—C10B59.77 (14)
C11A—N1A—C1A—C10A135.60 (11)C11B—N1B—C1B—C10B134.29 (12)
N1A—C1A—C2A—C3A178.38 (11)N1B—C1B—C2B—C3B176.55 (11)
C10A—C1A—C2A—C3A3.15 (18)C10B—C1B—C2B—C3B4.32 (18)
C1A—C2A—C3A—O1A179.48 (12)C1B—C2B—C3B—O1B179.43 (12)
C1A—C2A—C3A—C4A1.66 (18)C1B—C2B—C3B—C4B2.96 (17)
O1A—C3A—C4A—C5A1.75 (19)O1B—C3B—C4B—C5B3.17 (18)
C2A—C3A—C4A—C5A176.04 (11)C2B—C3B—C4B—C5B174.43 (11)
O1A—C3A—C4A—C9A179.21 (12)O1B—C3B—C4B—C9B176.20 (12)
C2A—C3A—C4A—C9A2.99 (17)C2B—C3B—C4B—C9B6.21 (17)
C9A—C4A—C5A—C6A0.46 (19)C9B—C4B—C5B—C6B0.20 (19)
C3A—C4A—C5A—C6A179.50 (12)C3B—C4B—C5B—C6B179.17 (12)
C4A—C5A—C6A—C7A0.6 (2)C4B—C5B—C6B—C7B0.9 (2)
C5A—C6A—C7A—C8A0.7 (2)C5B—C6B—C7B—C8B0.6 (2)
C6A—C7A—C8A—C9A0.6 (2)C6B—C7B—C8B—C9B0.8 (2)
C7A—C8A—C9A—C4A0.51 (19)C7B—C8B—C9B—C4B1.84 (19)
C7A—C8A—C9A—C10A179.45 (12)C7B—C8B—C9B—C10B178.24 (12)
C5A—C4A—C9A—C8A0.42 (18)C5B—C4B—C9B—C8B1.57 (18)
C3A—C4A—C9A—C8A179.46 (11)C3B—C4B—C9B—C8B177.80 (12)
C5A—C4A—C9A—C10A179.53 (11)C5B—C4B—C9B—C10B178.51 (11)
C3A—C4A—C9A—C10A0.49 (17)C3B—C4B—C9B—C10B2.11 (17)
C8A—C9A—C10A—O2A6.40 (18)C8B—C9B—C10B—O2B5.41 (19)
C4A—C9A—C10A—O2A173.65 (11)C4B—C9B—C10B—O2B174.51 (11)
C8A—C9A—C10A—C1A174.88 (11)C8B—C9B—C10B—C1B175.12 (11)
C4A—C9A—C10A—C1A5.08 (17)C4B—C9B—C10B—C1B4.96 (17)
C2A—C1A—C10A—O2A172.23 (12)C2B—C1B—C10B—O2B171.11 (12)
N1A—C1A—C10A—O2A6.34 (17)N1B—C1B—C10B—O2B8.09 (16)
C2A—C1A—C10A—C9A6.52 (17)C2B—C1B—C10B—C9B8.38 (17)
N1A—C1A—C10A—C9A174.91 (10)N1B—C1B—C10B—C9B172.42 (10)
C18A—N1A—C11A—O3A26.32 (17)C18B—N1B—C11B—O3B29.07 (17)
C1A—N1A—C11A—O3A136.86 (12)C1B—N1B—C11B—O3B136.30 (12)
C18A—N1A—C11A—C12A150.51 (11)C18B—N1B—C11B—C12B146.89 (11)
C1A—N1A—C11A—C12A46.31 (15)C1B—N1B—C11B—C12B47.74 (15)
O3A—C11A—C12A—C13A148.30 (13)O3B—C11B—C12B—C17B24.03 (17)
N1A—C11A—C12A—C13A28.45 (17)N1B—C11B—C12B—C17B160.09 (11)
O3A—C11A—C12A—C17A25.29 (18)O3B—C11B—C12B—C13B148.41 (12)
N1A—C11A—C12A—C17A157.96 (11)N1B—C11B—C12B—C13B27.47 (16)
C17A—C12A—C13A—C14A0.56 (19)C17B—C12B—C13B—C14B1.38 (18)
C11A—C12A—C13A—C14A174.05 (11)C11B—C12B—C13B—C14B173.64 (11)
C12A—C13A—C14A—C15A0.46 (19)C12B—C13B—C14B—C15B0.62 (19)
C13A—C14A—C15A—C16A0.7 (2)C13B—C14B—C15B—C16B0.0 (2)
C14A—C15A—C16A—C17A0.1 (2)C14B—C15B—C16B—C17B0.1 (2)
C15A—C16A—C17A—C12A1.1 (2)C15B—C16B—C17B—C12B0.9 (2)
C13A—C12A—C17A—C16A1.33 (19)C13B—C12B—C17B—C16B1.51 (19)
C11A—C12A—C17A—C16A174.98 (11)C11B—C12B—C17B—C16B174.05 (11)
C1A—N1A—C18A—O4A16.11 (17)C11B—N1B—C18B—O4B149.16 (12)
C11A—N1A—C18A—O4A147.96 (12)C1B—N1B—C18B—O4B17.25 (17)
C1A—N1A—C18A—C19A161.39 (11)C11B—N1B—C18B—C19B35.53 (16)
C11A—N1A—C18A—C19A34.55 (16)C1B—N1B—C18B—C19B158.06 (11)
O4A—C18A—C19A—C24A34.2 (2)O4B—C18B—C19B—C24B42.44 (19)
N1A—C18A—C19A—C24A148.34 (13)N1B—C18B—C19B—C24B142.42 (12)
O4A—C18A—C19A—C20A143.71 (14)O4B—C18B—C19B—C20B132.94 (14)
N1A—C18A—C19A—C20A33.72 (18)N1B—C18B—C19B—C20B42.21 (17)
C24A—C19A—C20A—C21A1.6 (2)C24B—C19B—C20B—C21B0.3 (2)
C18A—C19A—C20A—C21A179.56 (14)C18B—C19B—C20B—C21B175.65 (13)
C19A—C20A—C21A—C22A0.7 (3)C19B—C20B—C21B—C22B0.9 (2)
C20A—C21A—C22A—C23A2.0 (3)C20B—C21B—C22B—C23B0.6 (2)
C21A—C22A—C23A—C24A1.0 (3)C21B—C22B—C23B—C24B0.9 (2)
C20A—C19A—C24A—C23A2.6 (2)C20B—C19B—C24B—C23B1.8 (2)
C18A—C19A—C24A—C23A179.40 (14)C18B—C19B—C24B—C23B177.18 (13)
C22A—C23A—C24A—C19A1.3 (3)C22B—C23B—C24B—C19B2.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21A—H21A···O2Bi0.952.413.1270 (19)132
C14B—H14B···O3Aii0.952.503.4345 (17)168
C15B—H15B···O4Aiii0.952.623.4638 (17)148
C22B—H22B···O2A0.952.543.2054 (17)127
C14A—H14A···O3B0.952.443.2303 (16)140
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC24H15NO4
Mr381.37
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)9.8704 (11), 12.6776 (11), 15.6472 (14)
α, β, γ (°)90.735 (7), 98.213 (9), 108.187 (9)
V3)1837.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.52 × 0.28 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.751, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
26547, 26547, 17970
Rint0.0000
(sin θ/λ)max1)0.812
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.221, 1.03
No. of reflections26547
No. of parameters524
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.43

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21A—H21A···O2Bi0.952.413.1270 (19)132.1
C14B—H14B···O3Aii0.952.503.4345 (17)168.0
C15B—H15B···O4Aiii0.952.623.4638 (17)148.4
C22B—H22B···O2A0.952.543.2054 (17)127.4
C14A—H14A···O3B0.952.443.2303 (16)140.2
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+1, z+2.
 

Acknowledgements

RJB wishes to acknowledge the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer. We also acknowledge the MRI grant No. CHE-1126533 from the National Science Foundation for the purchase of a TOF LC/MS system used in this study, which was also funded in part by grant No. 5-U54-CA914-31 (Howard University/Johns Hopkins Cancer Center Partnership).

References

First citationAkinboye, E. S., Butcher, R. J., Brandy, Y., Adesiyun, T. A. & Bakare, O. (2009). Acta Cryst. E65, o24.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAkinboye, E. S., Butcher, R. J., Wright, D. A., Brandy, Y. & Bakare, O. (2009). Acta Cryst. E65, o277.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165–3170.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBerhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug Des. Discov. 5, 485–488.  CrossRef CAS Google Scholar
First citationKhraiwesh, H. M., Lee, C. M., Brandy, Y., Akinboye, E. S., Berhe, S., Gittens, G., Abbas, M. M., Ampy, F. R., Ashraf, M. & Bakare, O. (2011). Arch. Pharm. Res. 35, 27–33.  Web of Science CrossRef Google Scholar
First citationOxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds