supplementary materials


rn2117 scheme

Acta Cryst. (2013). E69, o1225    [ doi:10.1107/S1600536813018072 ]

3-[(E)-(Benzyliminiumyl)methyl]-6,8-dichloro-2H-chromen-4-olate

Y. Ishikawa and Y. Motohashi

Abstract top

In the title compound, C17H13Cl2NO2, the H atom of the -OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is a intramolecular O...H-N, rather than O-H...N, hydrogen bond, which forms a six-membered ring.

Comment top

Schiff bases of 3-formyl chromones have attracted much attention due to their biological functions such as enzyme inhibition (Khan et al. 2009; Tu et al. 2013). Here we report the crystal structure of the title compound, which was obtained from the condensation reaction of 6,8-dichloro-3-formylchromone with benzylamine and successive reduction by use of 2-picoline borane. The structure shows that the H atom of the –OH group is transferred to the N5 atom of the imine, thus forming a zwitterion. As a result, an intramolecular O···H–N [O···N = 2.7737 (19) Å], rather than O–H···N, hydrogen bond is formed. The bond distances O4–C8 [1.251 (2) Å], C8–C12 [1.432 (3) Å], C12–C14 [1.376 (3) Å] and C14–N5 [1.328 (3) Å] and torsion angles O4–C8–C12–C14 [–2.0 (3)°] and C8–C12–C14–N5 [0.6 (3)°] in the six-membered ring indicate charge delocalization among the atoms. This effect might be responsible for the preferential reduction of the α,β-unsaturated carbonyl of the synthetic intermediate, rather than reduction of the imine.

Related literature top

For the biological propertries of similar structures, see: Khan et al. (2009); Tu et al. (2013). For related structures, see: Benaouida et al. (2013); Małecka & Budzisz (2006).

Experimental top

Benzylamine (5 mmol), 6,8-dichloro-3-formylchromone (5 mmol) and 2-picoline borane (5 mmol) were dissolved in a mixture of MeOH-AcOH (10:1, 60 ml) and 2-propanol (20 ml), and stirred overnight at room temperature. Hydrochloric acid (1 M, 20 ml) was added to the reaction mixture, which was then stirred for 30 min. After neutralization with saturated NaHCO3, the mixture was extracted with methylene chloride. The extract was washed with brine, dried over anhydrous Na2SO4 and purified by column chromatography on silica gel (n-hexane: ethyl acetate = 3: 1). The eluted fractions were concentrated and filtered off. Layering n-hexane on the filtrate gave single crystals suitable for X-ray diffraction (yield 6%).

Refinement top

The carbon-bound hydrogen atoms were placed in geometrical positions [C–H 0.95 to 0.99 Å, Uiso(H) = 1.2Ueq(C)], and refined using a riding model. The hydrogen atom of the OH group was found to be located near N5 of the imine in a difference Fourier map, and refined with distance restraint [N–H 0.88 Å, Uiso(H) = 1.2Ueq(N)].

Computing details top

Data collection: WinAFC (Rigaku, 1999); cell refinement: WinAFC (Rigaku, 1999); data reduction: WinAFC (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
3-[(E)-(Benzyliminiumyl)methyl]-6,8-dichloro-2H-chromen-4-olate top
Crystal data top
C17H13Cl2NO2F(000) = 1376.00
Mr = 334.20Dx = 1.493 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 11.312 (5) Åθ = 15.3–17.4°
b = 28.284 (8) ŵ = 0.44 mm1
c = 9.294 (4) ÅT = 100 K
V = 2973.7 (19) Å3Prismatic, yellow
Z = 80.40 × 0.40 × 0.30 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.027
ω scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 814
Tmin = 0.734, Tmax = 0.876k = 036
4921 measured reflectionsl = 126
3411 independent reflections3 standard reflections every 150 reflections
2842 reflections with F2 > 2.0σ(F2) intensity decay: 0.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0484P)2 + 1.5727P]
where P = (Fo2 + 2Fc2)/3
3411 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.30 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C17H13Cl2NO2V = 2973.7 (19) Å3
Mr = 334.20Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.312 (5) ŵ = 0.44 mm1
b = 28.284 (8) ÅT = 100 K
c = 9.294 (4) Å0.40 × 0.40 × 0.30 mm
Data collection top
Rigaku AFC7R
diffractometer
2842 reflections with F2 > 2.0σ(F2)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.027
Tmin = 0.734, Tmax = 0.876θmax = 27.5°
4921 measured reflections3 standard reflections every 150 reflections
3411 independent reflections intensity decay: 0.7%
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.37 e Å3
S = 1.01Δρmin = 0.30 e Å3
3411 reflectionsAbsolute structure: ?
199 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.35615 (4)0.728872 (14)0.62619 (5)0.03107 (12)
Cl20.08088 (4)0.696080 (16)0.16439 (5)0.03462 (13)
O30.15191 (10)0.59834 (4)0.20309 (12)0.0270 (3)
O40.39867 (10)0.54598 (4)0.48567 (12)0.0250 (3)
N50.35872 (12)0.45877 (5)0.35813 (15)0.0254 (3)
C60.19963 (14)0.62709 (5)0.30470 (16)0.0225 (3)
C70.27643 (13)0.61039 (5)0.41191 (16)0.0207 (3)
C80.31307 (14)0.55972 (5)0.41132 (16)0.0214 (3)
C90.22286 (14)0.70675 (6)0.39517 (17)0.0250 (4)
C100.32453 (14)0.64196 (5)0.51118 (16)0.0214 (3)
C110.29724 (14)0.68935 (5)0.50180 (17)0.0230 (4)
C120.24579 (14)0.53004 (6)0.31714 (17)0.0232 (4)
C130.45884 (15)0.34680 (6)0.17648 (18)0.0281 (4)
C140.27199 (14)0.48304 (6)0.29639 (17)0.0245 (4)
C150.37317 (15)0.40812 (6)0.33640 (18)0.0266 (4)
C160.17522 (14)0.67549 (6)0.29714 (17)0.0245 (4)
C170.58227 (15)0.41186 (8)0.01394 (19)0.0354 (5)
C180.13558 (14)0.55016 (6)0.25306 (19)0.0262 (4)
C190.59128 (16)0.36417 (8)0.0169 (2)0.0383 (5)
C200.51113 (15)0.42726 (6)0.12718 (18)0.0286 (4)
C210.44961 (13)0.39468 (6)0.20942 (17)0.0226 (4)
C220.52919 (17)0.33175 (7)0.0642 (2)0.0360 (5)
H50.40910.47380.41400.0305*
H90.20520.73950.38990.0300*
H100.37580.63090.58480.0257*
H130.41630.32430.23190.0337*
H140.22300.46620.23110.0294*
H15A0.29400.39380.32330.0319*
H15B0.40810.39430.42450.0319*
H170.62470.43420.04220.0425*
H18A0.11040.53010.17130.0315*
H18B0.07180.54950.32600.0315*
H190.64020.35380.09370.0459*
H200.50490.46010.14790.0344*
H220.53490.29900.04260.0433*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0410 (3)0.0228 (2)0.0294 (3)0.00185 (17)0.00490 (18)0.00298 (15)
Cl20.0342 (3)0.0345 (3)0.0352 (3)0.00614 (17)0.01121 (18)0.00487 (18)
O30.0296 (6)0.0275 (6)0.0239 (6)0.0012 (5)0.0059 (5)0.0005 (5)
O40.0252 (6)0.0244 (6)0.0255 (6)0.0005 (5)0.0039 (5)0.0005 (5)
N50.0264 (7)0.0227 (7)0.0272 (7)0.0027 (6)0.0003 (6)0.0041 (6)
C60.0212 (8)0.0271 (8)0.0192 (7)0.0011 (6)0.0023 (6)0.0004 (6)
C70.0193 (7)0.0227 (8)0.0202 (7)0.0019 (6)0.0033 (6)0.0004 (6)
C80.0222 (8)0.0230 (7)0.0191 (7)0.0011 (6)0.0036 (6)0.0008 (6)
C90.0257 (8)0.0228 (8)0.0265 (8)0.0020 (7)0.0049 (7)0.0025 (7)
C100.0210 (8)0.0239 (8)0.0193 (7)0.0013 (6)0.0015 (6)0.0013 (6)
C110.0238 (8)0.0230 (8)0.0222 (8)0.0023 (6)0.0033 (7)0.0013 (6)
C120.0225 (8)0.0260 (8)0.0210 (8)0.0019 (7)0.0015 (7)0.0016 (6)
C130.0261 (8)0.0300 (9)0.0281 (9)0.0022 (7)0.0025 (7)0.0038 (7)
C140.0235 (8)0.0285 (8)0.0215 (8)0.0035 (7)0.0034 (7)0.0031 (6)
C150.0284 (9)0.0219 (8)0.0295 (9)0.0015 (7)0.0053 (7)0.0014 (7)
C160.0221 (8)0.0287 (8)0.0226 (8)0.0027 (7)0.0002 (7)0.0052 (6)
C170.0203 (9)0.0581 (12)0.0278 (9)0.0083 (8)0.0005 (7)0.0030 (9)
C180.0248 (8)0.0273 (8)0.0267 (8)0.0026 (7)0.0024 (7)0.0032 (7)
C190.0223 (9)0.0652 (14)0.0272 (9)0.0032 (9)0.0012 (7)0.0125 (9)
C200.0221 (8)0.0345 (9)0.0294 (9)0.0055 (7)0.0018 (7)0.0007 (7)
C210.0168 (7)0.0286 (8)0.0225 (8)0.0007 (6)0.0017 (6)0.0027 (6)
C220.0321 (10)0.0424 (10)0.0337 (10)0.0062 (8)0.0031 (8)0.0126 (8)
Geometric parameters (Å, º) top
Cl1—C111.7408 (17)C15—C211.512 (3)
Cl2—C161.7322 (18)C17—C191.383 (4)
O3—C61.3581 (19)C17—C201.395 (3)
O3—C181.451 (2)C19—C221.379 (3)
O4—C81.251 (2)C20—C211.385 (3)
N5—C141.328 (3)N5—H50.880
N5—C151.456 (3)C9—H90.950
C6—C71.404 (3)C10—H100.950
C6—C161.398 (3)C13—H130.950
C7—C81.492 (2)C14—H140.950
C7—C101.395 (2)C15—H15A0.990
C8—C121.432 (3)C15—H15B0.990
C9—C111.390 (3)C17—H170.950
C9—C161.379 (3)C18—H18A0.990
C10—C111.378 (2)C18—H18B0.990
C12—C141.376 (3)C19—H190.950
C12—C181.494 (3)C20—H200.950
C13—C211.392 (3)C22—H220.950
C13—C221.380 (3)
Cl2···O32.9012 (14)C6···H19v2.7245
O3···C82.874 (2)C7···H19v3.2656
O4···N52.7737 (19)C8···H14vi3.0884
O4···C102.851 (2)C8···H17v3.5062
O4···C142.884 (2)C8···H18Avii3.5501
N5···C82.943 (3)C9···H22vi3.2255
N5···C202.894 (3)C10···H13vi3.5411
C6···C112.771 (3)C10···H15Avi3.3524
C6···C122.797 (3)C10···H15Bii3.2487
C7···C92.796 (3)C11···H13vi3.2488
C7···C182.761 (3)C12···H17v3.1140
C10···C162.777 (3)C12···H20iii3.3837
C13···C172.760 (3)C13···H10ii2.9701
C14···C203.504 (3)C14···H17v3.5246
C14···C213.307 (3)C14···H17iii3.1469
C16···C183.596 (3)C14···H20iii3.1337
C19···C212.781 (3)C15···H10ii3.1335
C20···C222.772 (3)C15···H17iii3.4792
Cl1···C9i3.4408 (19)C15···H18Avi3.5736
Cl1···C13ii3.5107 (19)C16···H19v2.9361
Cl1···C22ii3.592 (3)C16···H22vi3.3726
Cl2···C11iii3.566 (2)C17···H14vii3.2418
O3···N5iv3.592 (3)C17···H15Avii2.8789
O3···C15iv3.425 (3)C17···H18Biv2.6983
O3···C19v3.544 (3)C18···H5iv3.2627
O4···O4ii3.4773 (18)C18···H15Biv3.4691
O4···N5ii3.108 (2)C18···H17vi3.5334
O4···C14vi3.569 (3)C18···H17v3.3747
O4···C15ii3.329 (3)C18···H20iii3.0867
O4···C18vii3.481 (3)C19···H15Avii3.0330
N5···O3vi3.592 (3)C19···H18Biv3.3900
N5···O4ii3.108 (2)C20···H10ii3.3922
N5···C17iii3.599 (3)C20···H14vii2.9477
C6···C19v3.579 (3)C20···H15Avii3.3691
C9···Cl1viii3.4408 (19)C20···H18Biv3.0242
C9···C22vi3.433 (3)C20···H18Bvii3.5530
C10···C13vi3.569 (3)C21···H10ii2.8430
C11···Cl2vii3.566 (2)C22···H10ii3.5942
C11···C13vi3.475 (3)H5···O3vi3.4434
C13···Cl1ii3.5107 (19)H5···O4ii2.4314
C13···C10iv3.569 (3)H5···C18vi3.2627
C13···C11iv3.475 (3)H5···H5ii2.9979
C14···O4iv3.569 (3)H5···H18Avi2.4038
C14···C17iii3.430 (3)H5···H18Avii2.8905
C14···C20iii3.421 (3)H5···H18Bvii3.5998
C15···O3vi3.425 (3)H9···Cl1viii3.1181
C15···O4ii3.329 (3)H9···Cl2i3.4352
C15···C17iii3.574 (3)H9···H13x3.1291
C16···C22vi3.398 (3)H9···H22vi3.2522
C17···N5vii3.599 (3)H9···H22ix3.4450
C17···C14vii3.430 (3)H10···C13ii2.9701
C17···C15vii3.574 (3)H10···C15ii3.1335
C18···O4iii3.481 (3)H10···C20ii3.3922
C19···O3v3.544 (3)H10···C21ii2.8430
C19···C6v3.579 (3)H10···C22ii3.5942
C20···C14vii3.421 (3)H10···H13ii3.1695
C22···Cl1ii3.592 (3)H10···H14vi3.2613
C22···C9iv3.433 (3)H10···H15Avi3.0153
C22···C16iv3.398 (3)H10···H15Bii2.5476
Cl1···H92.7981H13···Cl1iv3.5668
Cl1···H102.8069H13···Cl1ii3.2600
Cl2···H92.8075H13···C10iv3.5411
O4···H52.1512H13···C11iv3.2488
O4···H102.5850H13···H9xi3.1291
N5···H202.5602H13···H10ii3.1695
C6···H93.2783H14···O4iv2.6862
C6···H103.2801H14···C8iv3.0884
C6···H18A3.1745H14···C17iii3.2418
C6···H18B2.6342H14···C20iii2.9477
C7···H18B2.9925H14···H10iv3.2613
C8···H52.6624H14···H17iii3.2271
C8···H102.6746H14···H20iii2.7166
C8···H143.2926H15A···O3vi3.5892
C8···H18A3.3067H15A···C10iv3.3524
C8···H18B2.8563H15A···C17iii2.8789
C9···H103.2716H15A···C19iii3.0330
C10···H93.2726H15A···C20iii3.3691
C12···H52.5989H15A···H10iv3.0153
C13···H15A2.6653H15A···H17iii3.0194
C13···H15B2.7295H15A···H19iii3.2603
C13···H193.2485H15B···Cl2vi3.3943
C13···H203.2564H15B···O3vi2.6846
C14···H15A2.5490H15B···O4ii2.8852
C14···H15B3.1763H15B···C10ii3.2487
C14···H18A2.5431H15B···C18vi3.4691
C14···H18B2.9566H15B···H10ii2.5476
C14···H203.0445H15B···H17iii3.5708
C15···H132.6087H15B···H18Avi3.1415
C15···H142.5581H17···O3v3.0772
C15···H202.7292H17···N5vii3.2276
C17···H223.2478H17···C6v3.5927
C18···H142.5802H17···C8v3.5062
C19···H133.2458H17···C12v3.1140
C19···H203.2642H17···C14v3.5246
C20···H53.1890H17···C14vii3.1469
C20···H133.2529H17···C15vii3.4792
C20···H143.5740H17···C18iv3.5334
C20···H15A3.2015H17···C18v3.3747
C20···H15B3.1408H17···H14vii3.2271
C20···H193.2661H17···H15Avii3.0194
C21···H52.9716H17···H15Bvii3.5708
C21···H143.2721H17···H18Av3.3813
C21···H173.2625H17···H18Biv2.5793
C21···H223.2644H17···H20v3.4719
C22···H173.2473H18A···O4iv2.7604
H5···H142.7144H18A···O4iii2.8400
H5···H15A2.7426H18A···N5iv2.9479
H5···H15B2.2499H18A···N5iii3.5007
H5···H202.7282H18A···C8iii3.5501
H13···H15A2.5495H18A···C15iv3.5736
H13···H15B2.6719H18A···H5iv2.4038
H13···H222.3245H18A···H5iii2.8905
H14···H15A2.3613H18A···H15Biv3.1415
H14···H15B3.4285H18A···H17v3.3813
H14···H18A2.2803H18A···H20iii2.8599
H14···H18B3.0427H18B···O4iii3.4985
H14···H203.2864H18B···C17vi2.6983
H15A···H203.4440H18B···C19vi3.3900
H15B···H203.3569H18B···C20vi3.0242
H17···H192.3321H18B···C20iii3.5530
H17···H202.3436H18B···H5iii3.5998
H19···H222.3289H18B···H17vi2.5793
Cl1···H9i3.1181H18B···H20vi3.1266
Cl1···H13vi3.5668H18B···H20iii2.6531
Cl1···H13ii3.2600H19···Cl1xii3.5454
Cl1···H19ix3.5454H19···Cl2v3.5181
Cl1···H22ii3.4083H19···O3v2.8986
Cl1···H22ix2.8136H19···C6v2.7245
Cl2···H9viii3.4352H19···C7v3.2656
Cl2···H15Biv3.3943H19···C16v2.9361
Cl2···H19v3.5181H19···H15Avii3.2603
Cl2···H22x3.3865H20···O4ii3.5806
O3···H5iv3.4434H20···C12vii3.3837
O3···H15Aiv3.5892H20···C14vii3.1337
O3···H15Biv2.6846H20···C18vii3.0867
O3···H17v3.0772H20···H14vii2.7166
O3···H19v2.8986H20···H17v3.4719
O4···H5ii2.4314H20···H18Avii2.8599
O4···H14vi2.6862H20···H18Biv3.1266
O4···H15Bii2.8852H20···H18Bvii2.6531
O4···H18Avi2.7604H20···H20v3.5598
O4···H18Avii2.8400H22···Cl1ii3.4083
O4···H18Bvii3.4985H22···Cl1xii2.8136
O4···H20ii3.5806H22···Cl2xi3.3865
N5···H17iii3.2276H22···C9iv3.2255
N5···H18Avi2.9479H22···C16iv3.3726
N5···H18Avii3.5007H22···H9iv3.2522
C6···H17v3.5927H22···H9xii3.4450
C6—O3—C18112.97 (12)C15—C21—C20123.44 (16)
C14—N5—C15122.12 (14)C13—C22—C19120.12 (19)
O3—C6—C7122.55 (13)C14—N5—H5118.942
O3—C6—C16118.21 (14)C15—N5—H5118.939
C7—C6—C16119.16 (14)C11—C9—H9120.638
C6—C7—C8119.51 (13)C16—C9—H9120.643
C6—C7—C10119.71 (14)C7—C10—H10120.227
C8—C7—C10120.61 (14)C11—C10—H10120.204
O4—C8—C7120.75 (14)C21—C13—H13119.676
O4—C8—C12124.53 (14)C22—C13—H13119.686
C7—C8—C12114.69 (14)N5—C14—H14116.629
C11—C9—C16118.72 (16)C12—C14—H14116.629
C7—C10—C11119.57 (14)N5—C15—H15A108.564
Cl1—C11—C9118.55 (12)N5—C15—H15B108.559
Cl1—C11—C10119.79 (13)C21—C15—H15A108.561
C9—C11—C10121.67 (15)C21—C15—H15B108.557
C8—C12—C14122.53 (15)H15A—C15—H15B107.537
C8—C12—C18117.64 (15)C19—C17—H17119.888
C14—C12—C18119.47 (15)C20—C17—H17119.880
C21—C13—C22120.64 (16)O3—C18—H18A109.152
N5—C14—C12126.74 (16)O3—C18—H18B109.161
N5—C15—C21114.83 (14)C12—C18—H18A109.151
Cl2—C16—C6119.12 (13)C12—C18—H18B109.152
Cl2—C16—C9119.72 (13)H18A—C18—H18B107.860
C6—C16—C9121.15 (15)C17—C19—H19120.063
C19—C17—C20120.23 (18)C22—C19—H19120.065
O3—C18—C12112.27 (13)C17—C20—H20120.039
C17—C19—C22119.87 (18)C21—C20—H20120.047
C17—C20—C21119.91 (17)C13—C22—H22119.943
C13—C21—C15117.33 (15)C19—C22—H22119.938
C13—C21—C20119.22 (15)
C6—O3—C18—C1251.66 (17)C7—C10—C11—C90.2 (3)
C6—O3—C18—H18A172.8H10—C10—C11—Cl10.5
C6—O3—C18—H18B69.5H10—C10—C11—C9179.8
C18—O3—C6—C729.69 (19)C8—C12—C14—N50.6 (3)
C18—O3—C6—C16153.42 (12)C8—C12—C14—H14179.4
C14—N5—C15—C2189.40 (18)C8—C12—C18—O343.1 (2)
C14—N5—C15—H15A32.3C8—C12—C18—H18A164.3
C14—N5—C15—H15B148.9C8—C12—C18—H18B78.0
C15—N5—C14—C12175.36 (14)C14—C12—C18—O3143.61 (15)
C15—N5—C14—H144.6C14—C12—C18—H18A22.5
H5—N5—C14—C124.6C14—C12—C18—H18B95.2
H5—N5—C14—H14175.4C18—C12—C14—N5172.27 (14)
H5—N5—C15—C2190.6C18—C12—C14—H147.7
H5—N5—C15—H15A147.7C21—C13—C22—C190.0 (3)
H5—N5—C15—H15B31.1C21—C13—C22—H22180.0
O3—C6—C7—C83.3 (3)C22—C13—C21—C15178.49 (14)
O3—C6—C7—C10178.56 (12)C22—C13—C21—C200.6 (3)
O3—C6—C16—Cl22.8 (2)H13—C13—C21—C151.5
O3—C6—C16—C9178.65 (12)H13—C13—C21—C20179.4
C7—C6—C16—Cl2179.76 (12)H13—C13—C22—C19180.0
C7—C6—C16—C91.6 (3)H13—C13—C22—H220.0
C16—C6—C7—C8173.54 (13)N5—C15—C21—C13174.97 (12)
C16—C6—C7—C101.7 (3)N5—C15—C21—C206.0 (2)
C6—C7—C8—O4165.29 (13)H15A—C15—C21—C1353.3
C6—C7—C8—C1212.7 (2)H15A—C15—C21—C20127.7
C6—C7—C10—C110.8 (3)H15B—C15—C21—C1363.3
C6—C7—C10—H10179.2H15B—C15—C21—C20115.7
C8—C7—C10—C11174.38 (12)C19—C17—C20—C210.2 (3)
C8—C7—C10—H105.6C19—C17—C20—H20179.8
C10—C7—C8—O49.9 (3)C20—C17—C19—C220.4 (3)
C10—C7—C8—C12172.11 (13)C20—C17—C19—H19179.6
O4—C8—C12—C142.0 (3)H17—C17—C19—C22179.6
O4—C8—C12—C18171.05 (13)H17—C17—C19—H190.3
C7—C8—C12—C14175.92 (13)H17—C17—C20—C21179.8
C7—C8—C12—C1811.05 (19)H17—C17—C20—H200.2
C11—C9—C16—Cl2179.25 (12)C17—C19—C22—C130.5 (3)
C11—C9—C16—C60.7 (3)C17—C19—C22—H22179.5
C16—C9—C11—Cl1179.46 (13)H19—C19—C22—C13179.5
C16—C9—C11—C100.3 (3)H19—C19—C22—H220.5
H9—C9—C11—Cl10.5C17—C20—C21—C130.7 (3)
H9—C9—C11—C10179.7C17—C20—C21—C15178.32 (14)
H9—C9—C16—Cl20.8H20—C20—C21—C13179.3
H9—C9—C16—C6179.3H20—C20—C21—C151.7
C7—C10—C11—Cl1179.54 (12)
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x1/2, y, z+1/2; (iv) x+1/2, y+1, z1/2; (v) x+1, y+1, z; (vi) x+1/2, y+1, z+1/2; (vii) x+1/2, y, z+1/2; (viii) x, y+3/2, z1/2; (ix) x+1, y+1/2, z+1/2; (x) x+1/2, y+1/2, z; (xi) x+1/2, y1/2, z; (xii) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O40.882.152.7737 (19)127

Experimental details

Crystal data
Chemical formulaC17H13Cl2NO2
Mr334.20
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)100
a, b, c (Å)11.312 (5), 28.284 (8), 9.294 (4)
V3)2973.7 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.40 × 0.40 × 0.30
Data collection
DiffractometerRigaku AFC7R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.734, 0.876
No. of measured, independent and
observed [F2 > 2.0σ(F2)] reflections
4921, 3411, 2842
Rint0.027
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.095, 1.01
No. of reflections3411
No. of parameters199
No. of restraints0
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.30

Computer programs: WinAFC (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O40.8802.1512.7737 (19)127.2
Acknowledgements top

We acknowledge the University of Shizuoka for supporting this study.

references
References top

Benaouida, M. A., Chetioui, S. & Bouaoud, S. E. (2013). Acta Cryst. E69, o867–o868.

Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983–2988.

Małecka, M. & Budzisz, E. (2006). Acta Cryst. E62, o5058–o5060.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.

Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tu, Q. D., Li, D., Sun, Y., Han, X. Y., Yi, F., Sha, Y., Ren, Y. L., Ding, M. W., Feng, L. L. & Wan, J. (2013). Bioorg. Med. Chem. 21, 2826–2831.