Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 3| Part 10| October 2018| x181444
https://doi.org/10.1107/S241431461801444X

2-Amino-5-chloro­benzo­phenone

CROSSMARK_Color_square_no_text.svg
Saleem Javed,a Md. Serajul Haque Faizi,b* Siddiqui Naziaa and Turganbay Iskenderovc*

aDepartment of Chemistry, IHS, Khandari, Dr. Bhimrao Ambedkar University, Agra 208016, India, bDepartment of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, Bihar 842 001, India, and cNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
*Correspondence e-mail: faizichemiitg@gmail.com, tiskenderov@ukr.net

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 1 October 2018; accepted 13 October 2018; online 26 October 2018)

The asymmetric unit of the title compound (systematic name: 2-benzoyl-4-chloro­aniline), C13H10ClNO, contains four independent mol­ecules with similar dihedral angles between the benzene rings [ranging from 53.7 (2) to 59.8 (2)°]. In the crystal, the mol­ecules are linked by N—H⋯O hydrogen bonds into a three-dimensional supra­molecular architecture.

CCDC reference: 1873101

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Benzo­phenone derivatives often exhibit biological activities and are used as anti­allergic, anti-inflammatory, anti­asthamatic, anti­malarial, anti­microbial and anti­anaphylactic agents (Evans et al., 1987[Evans, D., Cracknell, M. E., Saunders, J. C., Smith, C. E., Williamson, W. R. N., Dawson, W. & Sweatman, W. J. F. (1987). J. Med. Chem. 30, 1321-1327.]; Wiesner et al., 2002[Wiesner, J., Kettler, K., Jomaa, H. & Schlitzer, M. (2002). Bioorg. Med. Chem. Lett. 12, 543-545.]; Sieroń et al., 2004[Sieroń, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889-o1891.]). 2-Amino­benzo­phenone and its derivatives are important because of their applications in heterocyclic synthesis and medicines (Walsh, 1980[Walsh, D. A. (1980). Synthesis, pp. 677-688.]). 2-Amino­benzo­phenone has been used as the starting material for the synthesis of 1,4-benzodiazepines (Sternbach et al., 1962[Sternbach, L. H., Fryer, R. I., Metlesics, W., Reeder, E., Sach, G., Saucy, G. & Stempel, A. (1962). J. Org. Chem. 27, 3788-3796.]) and anti-inflammatory agents (Ottosen et al., 2003[Ottosen, E. R., Sørensen, M. D., Björkling, F., Skak-Nielsen, T., Fjording, M. S., Aaes, H. & Binderup, L. (2003). J. Med. Chem. 46, 5651-5662.]) as well as peptido­amino­benzo­phenones, a class of open-ring derivatives of 1,4-benzodiazepines (Hirai et al., 1980[Hirai, K., Ishiba, T., Sugimoto, H., Sasakura, K., Fujishita, T., Toyoda, T., Tsukinoki, Y., Joyama, H., Hatakeyama, H. & Hirose, K. (1980). J. Med. Chem. 23, 764-773.]). 2-Amino­benzo­phenone derivatives have also been used as anti­mitotic agents (Liou et al., 2002[Liou, J. P., Chang, C. W., Song, J. S., Yang, Y. N., Yeh, C. F., Tseng, H. Y., Lo, Y. K., Chang, Y. L., Chang, C. M. & Hsieh, H. P. (2002). J. Med. Chem. 45, 2556-2562.]). Related mol­ecules, e.g. benzo­phenones-1, -2, -3, -4, -6, -8 and -12 (Wang & Lee, 2003[Wang, S.-P. & Lee, W.-T. (2003). J. Chromatogr. A, 987, 269-275.]), are used as sunscreen agents. The crystal structures of chlorinated benzo­phenones, such as 4-chloro-2-(3,4,5-tri­meth­oxy­benzo­yl)phenol (Hsieh et al., 2003[Hsieh, H. P., Liou, J. P., Lin, Y. T., Mahindroo, N., Chang, J. Y., Yang, Y. N., Chern, S. S., Tan, U. K., Chang, C. W., Chen, T. W., Lin, C. H., Chang, Y. Y. & Wang, C. C. (2003). Bioorg. Med. Chem. Lett. 13, 101-105.]) and pestalone (Cueto et al., 2001[Cueto, M., Jensen, P. R., Kauffman, C., Fenical, W., Lobkovsky, E. & Clardy, J. (2001). J. Nat. Prod. 64, 1444-1446.]), have also been determined and their role as potential anti­cancer agents and anti­biotics has been examined.

In the title compound (Fig. 1[link]), an intra­molecular hydrogen bond (Table 1[link]) between the carbonyl O and an amine H atom from the 2-amino­benzoyl group stabilizes each of the four independent mol­ecules and forms a six-membered ring. The dihedral angles between the benzene rings range from 53.7 (2) to 59.8 (2)°. This compares with values of 56° for benzo­phenone (Fleischer et al., 1968[Fleischer, E. B., Sung, N. & Hawkinson, S. (1968). J. Phys. Chem. 72, 4311-4312.]) and 54.39 (8)° for 2-methyl­amino-5-chloro­benzo­phenone (Cox et al., 1997[Cox, P. J., Anisuzzaman, A. T. Md., Skellern, G. G., Pryce-Jones, R. H., Florence, A. J. & Shankland, N. (1997). Acta Cryst. C53, 476-477.]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O2i 0.86 2.21 2.971 (5) 147
N1—H1B⋯O4 0.86 2.01 2.642 (5) 130
N2—H2A⋯O1ii 0.86 2.16 2.962 (4) 154
N2—H2B⋯O3 0.86 1.99 2.629 (4) 130
N3—H3A⋯O3 0.86 2.19 2.960 (4) 149
N3—H3B⋯O2 0.86 1.98 2.623 (4) 130
N4—H4A⋯O4 0.86 2.19 2.986 (5) 153
N4—H4B⋯O1 0.86 2.03 2.654 (5) 129
Symmetry codes: (i) x-1, y+1, z; (ii) x, y+1, z.
[Figure 1]
Figure 1
The four independent molecules in the asymmetric unit of the title compound showing the atom labelling scheme and 50% probability displacement ellipsoids.

In the crystal, N—H⋯O hydrogen bonds (Table 1[link]) link the mol­ecules into chains along [1[\overline{2}]0].

Synthesis and crystallization

The title compound was purchased from Sigma Aldrich and recrystallized by slow evaporation of an MeOH solution, prismatic colourless single crystals being obtained after four days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C13H10ClNO
Mr 231.67
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 273
a, b, c (Å) 9.7335 (7), 10.6473 (7), 24.7554 (17)
α, β, γ (°) 87.443 (2), 84.272 (2), 62.978 (2)
V (Å3) 2274.1 (3)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.31
Crystal size (mm) 0.25 × 0.15 × 0.10
 
Data collection
Diffractometer Bruker APEX CCD area detector
Absorption correction Empirical (using intensity measurements) (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.945, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections 34850, 11324, 4512
Rint 0.079
(sin θ/λ)max (Å−1) 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.225, 1.06
No. of reflections 11324
No. of parameters 577
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.23, −0.27
Computer programs: APEX2, SMART and SAINT-Plus (Bruker, 2007[Bruker (2007). APEX, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS86, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data

CCDC reference: 1873101

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431461801444X/xu4036sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461801444X/xu4036Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461801444X/xu4036Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-Benzoyl-4-chloroaniline top
Crystal data top
C13H10ClNOZ = 8
Mr = 231.67F(000) = 960
Triclinic, P1Dx = 1.353 Mg m−3
a = 9.7335 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6473 (7) ÅCell parameters from 11324 reflections
c = 24.7554 (17) Åθ = 2.2–28.4°
α = 87.443 (2)°µ = 0.31 mm−1
β = 84.272 (2)°T = 273 K
γ = 62.978 (2)°Prism, colorless
V = 2274.1 (3) Å30.25 × 0.15 × 0.10 mm
Data collection top
Bruker APEX CCD area detector
diffractometer		11324 independent reflections
Radiation source: fine-focus sealed tube4512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
phi and ω scansθmax = 28.4°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2001)		h = −12→12
Tmin = 0.945, Tmax = 0.969k = −14→14
34850 measured reflectionsl = −33→33
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)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0827P)2 + 0.4385P]
where P = (Fo2 + 2Fc2)/3
11324 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

All of the H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.88, C —H = 0.95 Å, and with Uĩso(H) = 1.18–1.21Ueq(C,N).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1−0.22973 (12)0.40371 (11)0.57327 (5)0.0702 (4)
Cl40.32333 (13)0.90689 (11)0.92390 (5)0.0699 (4)
Cl30.82354 (14)0.92281 (11)0.92846 (5)0.0726 (4)
Cl20.25035 (13)0.42264 (11)0.57452 (5)0.0742 (4)
O20.8276 (3)0.0336 (3)0.70037 (10)0.0603 (8)
O10.3672 (3)0.0469 (3)0.69319 (11)0.0660 (8)
O30.6319 (3)0.5398 (3)0.79903 (11)0.0618 (8)
O40.0801 (3)0.5417 (3)0.80924 (11)0.0638 (8)
N30.6669 (4)0.2790 (3)0.74839 (12)0.0612 (9)
H3A0.64440.34030.77350.073*
H3B0.74760.19890.74940.073*
N20.5589 (4)0.7840 (3)0.75068 (12)0.0608 (9)
H2A0.52410.84530.72530.073*
H2B0.55740.70410.74890.073*
C10.7822 (4)−0.0228 (4)0.61666 (14)0.0399 (9)
C20.6802 (4)0.7143 (4)0.83548 (15)0.0419 (9)
N40.1714 (4)0.2712 (4)0.75153 (13)0.0708 (11)
H4A0.14310.33180.77730.085*
H4B0.25660.19470.75210.085*
C30.2427 (4)0.4567 (4)0.87849 (15)0.0435 (9)
C40.1757 (4)0.6974 (4)0.83300 (15)0.0446 (9)
C50.7346 (4)0.4793 (4)0.88307 (14)0.0417 (9)
C60.5002 (4)0.2495 (4)0.62529 (15)0.0448 (9)
H60.51680.18540.59810.054*
C70.7443 (4)0.7518 (4)0.87631 (15)0.0446 (9)
H70.78840.68770.90380.054*
C80.6051 (4)0.2112 (4)0.66532 (14)0.0414 (9)
C90.6786 (4)0.5782 (4)0.83669 (15)0.0441 (9)
N10.0435 (4)0.7667 (4)0.75073 (13)0.0697 (10)
H1A0.00880.82630.72480.084*
H1B0.03440.69000.75140.084*
C100.2946 (4)−0.0435 (4)0.62334 (15)0.0460 (10)
C110.5753 (5)0.3087 (4)0.70726 (15)0.0470 (10)
C120.0196 (4)0.2353 (4)0.62564 (15)0.0466 (10)
H120.04460.17280.59700.056*
C130.2405 (4)0.7356 (4)0.87332 (15)0.0447 (9)
H130.27880.67420.90210.054*
C140.7410 (4)0.0742 (4)0.66330 (15)0.0422 (9)
C150.1613 (4)0.5656 (4)0.83826 (15)0.0467 (10)
C160.6155 (4)0.8130 (4)0.79311 (15)0.0467 (10)
C170.1186 (4)0.1997 (4)0.66732 (15)0.0456 (10)
C18−0.1129 (4)0.3602 (4)0.62636 (15)0.0463 (10)
C190.1906 (5)−0.0987 (4)0.61899 (15)0.0518 (10)
H190.0956−0.06090.63970.062*
C200.1119 (4)0.7934 (4)0.79014 (16)0.0513 (10)
C210.7963 (4)0.0193 (4)0.56358 (15)0.0505 (10)
H210.77450.11260.55610.061*
C220.0815 (5)0.2965 (4)0.70985 (15)0.0499 (10)
C520.2646 (5)0.0684 (4)0.66352 (15)0.0463 (10)
C230.8413 (4)0.3404 (4)0.87202 (16)0.0501 (10)
H230.87880.31240.83630.060*
C240.8145 (4)−0.1618 (4)0.62641 (16)0.0493 (10)
H240.8060−0.19170.66190.059*
C250.3751 (4)0.3784 (4)0.62560 (16)0.0479 (10)
C260.2493 (4)0.8601 (4)0.87180 (15)0.0478 (10)
C270.4016 (4)0.4008 (4)0.88200 (15)0.0491 (10)
H270.45910.43680.86030.059*
C280.8590 (4)−0.2570 (4)0.58436 (17)0.0547 (11)
H280.8799−0.35020.59160.066*
C290.6782 (4)0.5194 (4)0.93601 (16)0.0510 (10)
H290.60600.61200.94410.061*
C300.7437 (4)0.8804 (4)0.87671 (16)0.0502 (10)
C310.1272 (5)0.9185 (4)0.78939 (17)0.0614 (12)
H310.09110.98110.76070.074*
C320.8920 (5)0.2442 (4)0.91293 (18)0.0583 (11)
H320.96380.15150.90490.070*
C330.1927 (5)0.9517 (4)0.82900 (18)0.0597 (12)
H330.19951.03620.82730.072*
C340.3474 (5)0.4746 (4)0.66614 (18)0.0625 (12)
H340.26240.56310.66600.075*
C350.6778 (5)0.9772 (4)0.83648 (17)0.0602 (12)
H350.67491.06570.83740.072*
C360.1628 (5)0.3999 (4)0.91087 (17)0.0648 (12)
H360.05710.43430.90840.078*
C37−0.1510 (5)0.4535 (4)0.66879 (18)0.0589 (11)
H37−0.24130.53820.66940.071*
C38−0.0569 (5)0.4218 (4)0.70959 (17)0.0598 (12)
H38−0.08510.48510.73810.072*
C390.8723 (5)−0.2140 (4)0.53205 (19)0.0630 (12)
H390.9014−0.27760.50350.076*
C400.4736 (5)0.2923 (4)0.91764 (18)0.0650 (12)
H400.57980.25510.91980.078*
C410.6172 (5)0.9438 (4)0.79555 (17)0.0589 (11)
H410.57551.00950.76830.071*
C420.8373 (5)0.2840 (5)0.96577 (19)0.0630 (12)
H420.87260.21910.99380.076*
C430.2284 (5)−0.2083 (4)0.58428 (18)0.0632 (12)
H430.1597−0.24590.58180.076*
C440.4348 (5)−0.1013 (4)0.59149 (18)0.0649 (12)
H440.5056−0.06590.59390.078*
C450.7294 (5)0.4214 (4)0.97693 (16)0.0623 (12)
H450.69060.44841.01270.075*
C460.8425 (5)−0.0766 (4)0.52181 (16)0.0657 (12)
H460.8536−0.04800.48630.079*
C470.4442 (5)0.4398 (4)0.70622 (16)0.0581 (11)
H470.42300.50470.73360.070*
C480.3678 (5)−0.2631 (4)0.5530 (2)0.0725 (14)
H480.3928−0.33690.52910.087*
C490.3894 (6)0.2389 (4)0.94993 (19)0.0742 (14)
H490.43800.16560.97390.089*
C500.2337 (6)0.2945 (5)0.94652 (19)0.0765 (14)
H500.17580.26000.96880.092*
C510.4694 (5)−0.2091 (5)0.5569 (2)0.0806 (15)
H510.5634−0.24640.53560.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0616 (7)0.0552 (7)0.0837 (8)−0.0151 (6)−0.0241 (6)0.0102 (6)
Cl40.0772 (8)0.0564 (7)0.0854 (9)−0.0362 (6)−0.0124 (6)−0.0117 (6)
Cl30.0900 (9)0.0613 (7)0.0841 (9)−0.0463 (7)−0.0240 (7)−0.0006 (6)
Cl20.0572 (7)0.0612 (7)0.0912 (9)−0.0117 (6)−0.0290 (6)0.0080 (6)
O20.0649 (19)0.0551 (17)0.0468 (17)−0.0116 (15)−0.0217 (15)0.0016 (13)
O10.072 (2)0.0572 (18)0.070 (2)−0.0249 (16)−0.0351 (17)0.0057 (15)
O30.087 (2)0.0549 (17)0.0497 (17)−0.0348 (16)−0.0201 (16)−0.0029 (13)
O40.075 (2)0.0559 (18)0.0651 (19)−0.0282 (16)−0.0307 (16)−0.0019 (14)
N30.081 (3)0.053 (2)0.048 (2)−0.0266 (19)−0.009 (2)−0.0068 (17)
N20.075 (2)0.058 (2)0.044 (2)−0.0249 (19)−0.0133 (18)0.0072 (17)
C10.036 (2)0.036 (2)0.043 (2)−0.0107 (17)−0.0071 (17)0.0017 (17)
C20.040 (2)0.043 (2)0.042 (2)−0.0187 (19)−0.0002 (18)−0.0018 (18)
N40.100 (3)0.063 (2)0.055 (2)−0.038 (2)−0.019 (2)−0.0048 (18)
C30.044 (2)0.035 (2)0.052 (2)−0.0168 (19)−0.010 (2)−0.0053 (18)
C40.041 (2)0.041 (2)0.041 (2)−0.0099 (19)−0.0013 (18)−0.0035 (18)
C50.044 (2)0.041 (2)0.042 (2)−0.0208 (19)−0.0040 (19)−0.0014 (18)
C60.044 (2)0.036 (2)0.051 (2)−0.0144 (19)−0.0028 (19)−0.0020 (18)
C70.046 (2)0.036 (2)0.049 (2)−0.0172 (19)−0.0029 (19)0.0027 (17)
C80.045 (2)0.039 (2)0.042 (2)−0.0213 (19)−0.0009 (19)0.0024 (18)
C90.043 (2)0.045 (2)0.041 (2)−0.0176 (19)−0.0026 (18)−0.0065 (19)
N10.084 (3)0.064 (2)0.051 (2)−0.020 (2)−0.028 (2)0.0092 (18)
C100.045 (3)0.037 (2)0.054 (3)−0.015 (2)−0.018 (2)0.0035 (18)
C110.056 (3)0.045 (2)0.044 (2)−0.027 (2)−0.003 (2)−0.0013 (19)
C120.052 (3)0.040 (2)0.048 (2)−0.021 (2)−0.005 (2)0.0022 (18)
C130.049 (2)0.039 (2)0.043 (2)−0.0172 (19)−0.0048 (19)0.0006 (17)
C140.043 (2)0.038 (2)0.045 (2)−0.0177 (19)−0.007 (2)0.0018 (18)
C150.048 (2)0.043 (2)0.045 (2)−0.015 (2)−0.008 (2)−0.0077 (18)
C160.044 (2)0.046 (2)0.043 (2)−0.014 (2)−0.0020 (19)0.0022 (19)
C170.057 (3)0.043 (2)0.040 (2)−0.026 (2)−0.003 (2)0.0036 (18)
C180.043 (2)0.041 (2)0.054 (3)−0.019 (2)−0.0020 (19)0.0025 (19)
C190.052 (3)0.048 (2)0.055 (3)−0.021 (2)−0.016 (2)0.009 (2)
C200.045 (2)0.047 (2)0.046 (3)−0.007 (2)−0.002 (2)0.001 (2)
C210.058 (3)0.038 (2)0.047 (3)−0.014 (2)−0.007 (2)0.0028 (19)
C220.069 (3)0.052 (3)0.040 (2)−0.038 (2)−0.001 (2)0.003 (2)
C520.056 (3)0.040 (2)0.045 (2)−0.022 (2)−0.013 (2)0.0093 (18)
C230.053 (3)0.043 (2)0.053 (3)−0.021 (2)0.002 (2)−0.008 (2)
C240.046 (2)0.041 (2)0.056 (3)−0.015 (2)−0.006 (2)0.004 (2)
C250.043 (2)0.037 (2)0.057 (3)−0.012 (2)−0.0074 (19)0.0043 (19)
C260.047 (2)0.040 (2)0.054 (3)−0.0183 (19)0.003 (2)−0.0048 (19)
C270.048 (3)0.046 (2)0.055 (3)−0.022 (2)−0.008 (2)−0.005 (2)
C280.053 (3)0.041 (2)0.071 (3)−0.022 (2)−0.002 (2)−0.004 (2)
C290.059 (3)0.040 (2)0.052 (3)−0.021 (2)−0.004 (2)−0.003 (2)
C300.057 (3)0.039 (2)0.054 (3)−0.020 (2)−0.005 (2)−0.0039 (19)
C310.068 (3)0.049 (3)0.054 (3)−0.016 (2)−0.007 (2)0.013 (2)
C320.053 (3)0.039 (2)0.077 (3)−0.016 (2)−0.002 (2)0.002 (2)
C330.062 (3)0.040 (2)0.069 (3)−0.019 (2)0.011 (2)0.001 (2)
C340.056 (3)0.040 (2)0.073 (3)−0.007 (2)0.003 (2)−0.003 (2)
C350.073 (3)0.041 (2)0.064 (3)−0.025 (2)0.001 (2)0.003 (2)
C360.059 (3)0.069 (3)0.083 (3)−0.041 (3)−0.023 (3)0.019 (3)
C370.057 (3)0.044 (2)0.070 (3)−0.021 (2)0.012 (2)−0.005 (2)
C380.073 (3)0.052 (3)0.057 (3)−0.032 (3)0.005 (3)−0.012 (2)
C390.067 (3)0.055 (3)0.065 (3)−0.025 (2)−0.001 (2)−0.021 (2)
C400.061 (3)0.045 (3)0.084 (3)−0.016 (2)−0.027 (3)−0.003 (2)
C410.069 (3)0.046 (3)0.054 (3)−0.020 (2)−0.008 (2)0.015 (2)
C420.064 (3)0.058 (3)0.069 (3)−0.027 (3)−0.018 (3)0.021 (2)
C430.064 (3)0.047 (3)0.084 (3)−0.026 (2)−0.032 (3)0.005 (2)
C440.039 (3)0.062 (3)0.091 (3)−0.019 (2)−0.007 (2)−0.012 (3)
C450.083 (3)0.060 (3)0.046 (3)−0.034 (3)−0.004 (2)0.004 (2)
C460.080 (3)0.059 (3)0.047 (3)−0.023 (3)0.000 (2)−0.005 (2)
C470.072 (3)0.043 (2)0.051 (3)−0.019 (2)0.004 (2)−0.012 (2)
C480.062 (3)0.044 (3)0.097 (4)−0.007 (2)−0.019 (3)−0.018 (2)
C490.098 (4)0.047 (3)0.084 (4)−0.034 (3)−0.044 (3)0.021 (2)
C500.080 (4)0.084 (4)0.087 (4)−0.054 (3)−0.030 (3)0.033 (3)
C510.049 (3)0.074 (3)0.107 (4)−0.016 (3)−0.002 (3)−0.028 (3)
Geometric parameters (Å, º) top
Cl1—C181.732 (4)C18—C371.381 (5)
Cl4—C261.732 (4)C19—C431.368 (5)
Cl3—C301.737 (4)C19—H190.9300
Cl2—C251.740 (4)C20—C311.405 (5)
O2—C141.236 (4)C21—C461.378 (5)
O1—C521.230 (4)C21—H210.9300
O3—C91.237 (4)C22—C381.401 (5)
O4—C151.232 (4)C23—C321.366 (5)
N3—C111.352 (5)C23—H230.9300
N3—H3A0.8600C24—C281.380 (5)
N3—H3B0.8600C24—H240.9300
N2—C161.342 (5)C25—C341.384 (5)
N2—H2A0.8600C26—C331.383 (5)
N2—H2B0.8600C27—C401.379 (5)
C1—C241.381 (5)C27—H270.9300
C1—C211.383 (5)C28—C391.368 (5)
C1—C141.483 (5)C28—H280.9300
C2—C71.399 (5)C29—C451.378 (5)
C2—C161.426 (5)C29—H290.9300
C2—C91.455 (5)C30—C351.379 (5)
N4—C221.358 (5)C31—C331.361 (6)
N4—H4A0.8600C31—H310.9300
N4—H4B0.8600C32—C421.371 (5)
C3—C361.368 (5)C32—H320.9300
C3—C271.393 (5)C33—H330.9300
C3—C151.478 (5)C34—C471.359 (6)
C4—C131.398 (5)C34—H340.9300
C4—C201.419 (5)C35—C411.358 (5)
C4—C151.471 (5)C35—H350.9300
C5—C291.377 (5)C36—C501.358 (5)
C5—C231.387 (5)C36—H360.9300
C5—C91.490 (5)C37—C381.359 (6)
C6—C251.359 (5)C37—H370.9300
C6—C81.406 (5)C38—H380.9300
C6—H60.9300C39—C461.372 (5)
C7—C301.367 (5)C39—H390.9300
C7—H70.9300C40—C491.373 (6)
C8—C111.415 (5)C40—H400.9300
C8—C141.456 (5)C41—H410.9300
N1—C201.343 (5)C42—C451.379 (5)
N1—H1A0.8600C42—H420.9300
N1—H1B0.8600C43—C481.377 (6)
C10—C441.389 (5)C43—H430.9300
C10—C191.397 (5)C44—C511.358 (6)
C10—C521.491 (5)C44—H440.9300
C11—C471.401 (5)C45—H450.9300
C12—C181.368 (5)C46—H460.9300
C12—C171.403 (5)C47—H470.9300
C12—H120.9300C48—C511.363 (6)
C13—C261.366 (5)C48—H480.9300
C13—H130.9300C49—C501.363 (6)
C16—C411.404 (5)C49—H490.9300
C17—C221.408 (5)C50—H500.9300
C17—C521.471 (5)C51—H510.9300
C11—N3—H3A120.0C28—C24—C1121.1 (4)
C11—N3—H3B120.0C28—C24—H24119.4
H3A—N3—H3B120.0C1—C24—H24119.4
C16—N2—H2A120.0C6—C25—C34120.2 (4)
C16—N2—H2B120.0C6—C25—Cl2119.7 (3)
H2A—N2—H2B120.0C34—C25—Cl2120.0 (3)
C24—C1—C21118.5 (3)C13—C26—C33119.1 (4)
C24—C1—C14119.1 (3)C13—C26—Cl4120.8 (3)
C21—C1—C14122.3 (3)C33—C26—Cl4120.0 (3)
C7—C2—C16118.4 (3)C40—C27—C3120.0 (4)
C7—C2—C9120.6 (3)C40—C27—H27120.0
C16—C2—C9121.0 (3)C3—C27—H27120.0
C22—N4—H4A120.0C39—C28—C24119.8 (4)
C22—N4—H4B120.0C39—C28—H28120.1
H4A—N4—H4B120.0C24—C28—H28120.1
C36—C3—C27118.0 (4)C5—C29—C45119.5 (4)
C36—C3—C15119.4 (3)C5—C29—H29120.3
C27—C3—C15122.4 (4)C45—C29—H29120.3
C13—C4—C20118.9 (4)C7—C30—C35120.0 (4)
C13—C4—C15119.8 (3)C7—C30—Cl3120.0 (3)
C20—C4—C15121.0 (4)C35—C30—Cl3120.0 (3)
C29—C5—C23119.2 (3)C33—C31—C20122.5 (4)
C29—C5—C9122.2 (3)C33—C31—H31118.7
C23—C5—C9118.5 (3)C20—C31—H31118.7
C25—C6—C8121.3 (4)C23—C32—C42120.1 (4)
C25—C6—H6119.4C23—C32—H32119.9
C8—C6—H6119.4C42—C32—H32119.9
C30—C7—C2121.6 (4)C31—C33—C26120.2 (4)
C30—C7—H7119.2C31—C33—H33119.9
C2—C7—H7119.2C26—C33—H33119.9
C6—C8—C11118.5 (3)C47—C34—C25120.1 (4)
C6—C8—C14120.4 (3)C47—C34—H34120.0
C11—C8—C14121.1 (3)C25—C34—H34120.0
O3—C9—C2121.3 (3)C41—C35—C30120.1 (4)
O3—C9—C5117.5 (3)C41—C35—H35119.9
C2—C9—C5121.3 (3)C30—C35—H35119.9
C20—N1—H1A120.0C50—C36—C3121.8 (4)
C20—N1—H1B120.0C50—C36—H36119.1
H1A—N1—H1B120.0C3—C36—H36119.1
C44—C10—C19118.6 (4)C38—C37—C18120.2 (4)
C44—C10—C52119.1 (4)C38—C37—H37119.9
C19—C10—C52122.2 (4)C18—C37—H37119.9
N3—C11—C47119.2 (4)C37—C38—C22121.8 (4)
N3—C11—C8122.5 (3)C37—C38—H38119.1
C47—C11—C8118.3 (4)C22—C38—H38119.1
C18—C12—C17121.2 (4)C28—C39—C46119.7 (4)
C18—C12—H12119.4C28—C39—H39120.1
C17—C12—H12119.4C46—C39—H39120.1
C26—C13—C4122.2 (4)C49—C40—C27120.3 (4)
C26—C13—H13118.9C49—C40—H40119.8
C4—C13—H13118.9C27—C40—H40119.8
O2—C14—C8121.4 (3)C35—C41—C16122.1 (4)
O2—C14—C1117.0 (3)C35—C41—H41119.0
C8—C14—C1121.6 (3)C16—C41—H41119.0
O4—C15—C4121.2 (4)C32—C42—C45119.2 (4)
O4—C15—C3117.1 (3)C32—C42—H42120.4
C4—C15—C3121.7 (3)C45—C42—H42120.4
N2—C16—C41119.4 (4)C19—C43—C48120.2 (4)
N2—C16—C2122.9 (4)C19—C43—H43119.9
C41—C16—C2117.7 (4)C48—C43—H43119.9
C12—C17—C22118.9 (4)C51—C44—C10120.5 (4)
C12—C17—C52119.6 (3)C51—C44—H44119.8
C22—C17—C52121.3 (4)C10—C44—H44119.8
C12—C18—C37119.8 (4)C29—C45—C42121.1 (4)
C12—C18—Cl1120.1 (3)C29—C45—H45119.5
C37—C18—Cl1120.0 (3)C42—C45—H45119.5
C43—C19—C10120.0 (4)C39—C46—C21120.7 (4)
C43—C19—H19120.0C39—C46—H46119.6
C10—C19—H19120.0C21—C46—H46119.6
N1—C20—C31120.3 (4)C34—C47—C11121.7 (4)
N1—C20—C4122.7 (4)C34—C47—H47119.2
C31—C20—C4117.0 (4)C11—C47—H47119.2
C46—C21—C1120.1 (4)C51—C48—C43120.0 (4)
C46—C21—H21120.0C51—C48—H48120.0
C1—C21—H21120.0C43—C48—H48120.0
N4—C22—C38119.1 (4)C50—C49—C40119.4 (4)
N4—C22—C17122.8 (4)C50—C49—H49120.3
C38—C22—C17118.0 (4)C40—C49—H49120.3
O1—C52—C17121.2 (4)C36—C50—C49120.4 (4)
O1—C52—C10117.4 (3)C36—C50—H50119.8
C17—C52—C10121.4 (3)C49—C50—H50119.8
C32—C23—C5120.9 (4)C44—C51—C48120.8 (4)
C32—C23—H23119.6C44—C51—H51119.6
C5—C23—H23119.6C48—C51—H51119.6
C16—C2—C7—C301.0 (5)C44—C10—C52—O1−47.5 (5)
C9—C2—C7—C30−178.4 (3)C19—C10—C52—O1128.3 (4)
C25—C6—C8—C111.8 (5)C44—C10—C52—C17132.0 (4)
C25—C6—C8—C14−178.1 (3)C19—C10—C52—C17−52.2 (5)
C7—C2—C9—O3−175.1 (3)C29—C5—C23—C32−0.8 (6)
C16—C2—C9—O35.5 (6)C9—C5—C23—C32−177.6 (4)
C7—C2—C9—C54.3 (5)C21—C1—C24—C28−0.4 (5)
C16—C2—C9—C5−175.1 (3)C14—C1—C24—C28−177.5 (3)
C29—C5—C9—O3−126.8 (4)C8—C6—C25—C34−0.8 (6)
C23—C5—C9—O349.9 (5)C8—C6—C25—Cl2178.8 (3)
C29—C5—C9—C253.8 (5)C4—C13—C26—C33−0.1 (6)
C23—C5—C9—C2−129.5 (4)C4—C13—C26—Cl4177.4 (3)
C6—C8—C11—N3177.7 (3)C36—C3—C27—C40−0.5 (6)
C14—C8—C11—N3−2.3 (6)C15—C3—C27—C40−175.4 (3)
C6—C8—C11—C47−1.2 (5)C1—C24—C28—C390.3 (6)
C14—C8—C11—C47178.7 (3)C23—C5—C29—C450.4 (6)
C20—C4—C13—C26−2.4 (6)C9—C5—C29—C45177.1 (4)
C15—C4—C13—C26−176.6 (3)C2—C7—C30—C350.5 (6)
C6—C8—C14—O2−173.9 (3)C2—C7—C30—Cl3179.6 (3)
C11—C8—C14—O26.2 (5)N1—C20—C31—C33178.6 (4)
C6—C8—C14—C16.3 (5)C4—C20—C31—C33−3.2 (6)
C11—C8—C14—C1−173.6 (3)C5—C23—C32—C420.2 (6)
C24—C1—C14—O249.8 (5)C20—C31—C33—C260.8 (6)
C21—C1—C14—O2−127.2 (4)C13—C26—C33—C310.9 (6)
C24—C1—C14—C8−130.4 (4)Cl4—C26—C33—C31−176.6 (3)
C21—C1—C14—C852.6 (5)C6—C25—C34—C47−0.8 (6)
C13—C4—C15—O4166.5 (3)Cl2—C25—C34—C47179.6 (3)
C20—C4—C15—O4−7.7 (6)C7—C30—C35—C41−1.8 (6)
C13—C4—C15—C3−13.3 (5)Cl3—C30—C35—C41179.1 (3)
C20—C4—C15—C3172.5 (3)C27—C3—C36—C501.6 (6)
C36—C3—C15—O4−47.7 (5)C15—C3—C36—C50176.6 (4)
C27—C3—C15—O4127.2 (4)C12—C18—C37—C380.3 (6)
C36—C3—C15—C4132.2 (4)Cl1—C18—C37—C38−177.8 (3)
C27—C3—C15—C4−53.0 (5)C18—C37—C38—C221.1 (6)
C7—C2—C16—N2176.4 (3)N4—C22—C38—C37179.4 (4)
C9—C2—C16—N2−4.2 (6)C17—C22—C38—C37−2.6 (6)
C7—C2—C16—C41−1.3 (5)C24—C28—C39—C460.5 (6)
C9—C2—C16—C41178.1 (3)C3—C27—C40—C49−0.2 (6)
C18—C12—C17—C22−1.5 (5)C30—C35—C41—C161.6 (6)
C18—C12—C17—C52−176.4 (3)N2—C16—C41—C35−177.7 (4)
C17—C12—C18—C37−0.1 (6)C2—C16—C41—C350.0 (6)
C17—C12—C18—Cl1178.0 (3)C23—C32—C42—C450.8 (6)
C44—C10—C19—C430.6 (6)C10—C19—C43—C48−1.0 (6)
C52—C10—C19—C43−175.2 (3)C19—C10—C44—C510.1 (6)
C13—C4—C20—N1−178.0 (3)C52—C10—C44—C51176.1 (4)
C15—C4—C20—N1−3.8 (6)C5—C29—C45—C420.6 (6)
C13—C4—C20—C313.9 (5)C32—C42—C45—C29−1.2 (7)
C15—C4—C20—C31178.1 (3)C28—C39—C46—C21−1.3 (7)
C24—C1—C21—C46−0.4 (6)C1—C21—C46—C391.2 (6)
C14—C1—C21—C46176.7 (4)C25—C34—C47—C111.4 (6)
C12—C17—C22—N4−179.4 (3)N3—C11—C47—C34−179.3 (4)
C52—C17—C22—N4−4.5 (6)C8—C11—C47—C34−0.4 (6)
C12—C17—C22—C382.7 (5)C19—C43—C48—C510.7 (7)
C52—C17—C22—C38177.5 (3)C27—C40—C49—C50−0.2 (7)
C12—C17—C52—O1165.7 (3)C3—C36—C50—C49−1.9 (7)
C22—C17—C52—O1−9.1 (6)C40—C49—C50—C361.2 (7)
C12—C17—C52—C10−13.9 (5)C10—C44—C51—C48−0.4 (7)
C22—C17—C52—C10171.3 (3)C43—C48—C51—C440.0 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.212.971 (5)147
N1—H1B···O40.862.012.642 (5)130
N2—H2A···O1ii0.862.162.962 (4)154
N2—H2B···O30.861.992.629 (4)130
N3—H3A···O30.862.192.960 (4)149
N3—H3B···O20.861.982.623 (4)130
N4—H4A···O40.862.192.986 (5)153
N4—H4B···O10.862.032.654 (5)129
Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z.
 

Acknowledgements

The authors are grateful to the Department of Chemistry, National Taras Shevchenko University, for financial support, and to the Department of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, India, for providing a laboratory.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2007). APEX, SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCox, P. J., Anisuzzaman, A. T. Md., Skellern, G. G., Pryce-Jones, R. H., Florence, A. J. & Shankland, N. (1997). Acta Cryst. C53, 476–477.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationCueto, M., Jensen, P. R., Kauffman, C., Fenical, W., Lobkovsky, E. & Clardy, J. (2001). J. Nat. Prod. 64, 1444–1446.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationEvans, D., Cracknell, M. E., Saunders, J. C., Smith, C. E., Williamson, W. R. N., Dawson, W. & Sweatman, W. J. F. (1987). J. Med. Chem. 30, 1321–1327.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFleischer, E. B., Sung, N. & Hawkinson, S. (1968). J. Phys. Chem. 72, 4311–4312.  CSD CrossRef CAS Web of Science Google Scholar
 First citationHirai, K., Ishiba, T., Sugimoto, H., Sasakura, K., Fujishita, T., Toyoda, T., Tsukinoki, Y., Joyama, H., Hatakeyama, H. & Hirose, K. (1980). J. Med. Chem. 23, 764–773.  CrossRef PubMed Web of Science Google Scholar
 First citationHsieh, H. P., Liou, J. P., Lin, Y. T., Mahindroo, N., Chang, J. Y., Yang, Y. N., Chern, S. S., Tan, U. K., Chang, C. W., Chen, T. W., Lin, C. H., Chang, Y. Y. & Wang, C. C. (2003). Bioorg. Med. Chem. Lett. 13, 101–105.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationLiou, J. P., Chang, C. W., Song, J. S., Yang, Y. N., Yeh, C. F., Tseng, H. Y., Lo, Y. K., Chang, Y. L., Chang, C. M. & Hsieh, H. P. (2002). J. Med. Chem. 45, 2556–2562.  Web of Science CrossRef PubMed Google Scholar
 First citationOttosen, E. R., Sørensen, M. D., Björkling, F., Skak-Nielsen, T., Fjording, M. S., Aaes, H. & Binderup, L. (2003). J. Med. Chem. 46, 5651–5662.  Web of Science CrossRef PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSieroń, L., Shashikanth, S., Yathirajan, H. S., Venu, T. D., Nagaraj, B., Nagaraja, P. & Khanum, S. A. (2004). Acta Cryst. E60, o1889–o1891.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSternbach, L. H., Fryer, R. I., Metlesics, W., Reeder, E., Sach, G., Saucy, G. & Stempel, A. (1962). J. Org. Chem. 27, 3788–3796.  CrossRef Web of Science Google Scholar
 First citationWalsh, D. A. (1980). Synthesis, pp. 677–688.  CrossRef Google Scholar
 First citationWang, S.-P. & Lee, W.-T. (2003). J. Chromatogr. A, 987, 269–275.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationWiesner, J., Kettler, K., Jomaa, H. & Schlitzer, M. (2002). Bioorg. Med. Chem. Lett. 12, 543–545.  Web of Science CrossRef PubMed CAS 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 logoIUCrDATA
ISSN: 2414-3146
Volume 3| Part 10| October 2018| x181444
https://doi.org/10.1107/S241431461801444X
Follow IUCr Journals
Sign up for e-alerts
E-alerts
Follow IUCr on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS