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The title mol­ecule, C21H15Cl2N3O, consists of two coplanar 4-chloro­phenyl groups bonded to a distorted (envelope) dihydro­quinazoline ring with a dihedral angle of 58.9 (1)° between the 4-chlorophenyl groups. The angles between the mean planes of the benzyl group of the nonplanar dihydro­quinazoline group and those of the two 4-chloro­phenyl groups are 82.0 (6) and 84.3 (3)°, respectively. The torsion angle of the methyl­ene amine linkage indicates a significant twist between the dihydro­quinazolin-4(1H)-one and attached 4-chloro­phenyl group. Disordered chlorine atoms (0.86:0.14) occur within the singly attached 4-chloro­phenyl group bonded to the dihydro­quinazoline ring. Crystal packing is stabilized by inter­molecular N—H...O hydrogen bonding between dihydro­quinazoline groups, linking the mol­ecules into chains along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043632/nc2054sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043632/nc2054Isup2.hkl
Contains datablock I

CCDC reference: 663741

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.045
  • wR factor = 0.055
  • Data-to-parameter ratio = 25.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.10 Deg. CL2B -C12 -CL2A 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.955 Tmax scaled 0.955 Tmin scaled 0.885 PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Substituted 2,3-dihydroquinazolin-4(1H)-ones are found to be potent inhibitors of inosine 5'-monophosphate dehydrogenase type II (Birch et al., 2005) and also are found to possess antibacterial (Alaimo & Russel, 1972) and anthelmentic activities (Alaimo & Hatton, 1972). Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh & Dash, 1988; Varma et al., 1986), antitumor (Hodnett & Dunn, 1970., Misra et al., 1981; Desai et al., 2001), and also act as herbicides. The crystal structures of 3-(4-bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Shi, Li, Shi, Zhuang & Zhang, 2004), 3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (Shi et al., 2004a), 6-chloro-3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one acetone hemisolvate (Shi et al., 2004b), 7-chloro-2,2-dimethyl-3-(4-methylphenyl)-1,2-dihydroquinazolin-4(3H)-one (Shi, Shi et al., 2004), 2-(4-hydroxy-3-methoxyphenyl)-1-phenethyl-1,2-dihydroquinazolin-4(3H)-one (Swamy & Ravikumar, 2005), 5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Vembu et al., 2006) and 2-(biphenyl-4-yl)-2,3-dihydroquinazolin-4(1H)-one (Chruszcz et al., 2007) have been reported. A new quinazolinone containing Schiff base, C21H15Cl2N3O, has been synthesized and its crystal structure is reported. In our synthesis we expected the formation of 2-amino-N'-[(1E)-(4- chlorophenyl)methylene]benzohydrazide. Instead the aldehyde reacted with both primary amino groups and the cyclized form was created producing the title compound, (I).

The six-membered pyrimidin-4(1H)-one ring within the quinazoline group (C1—C2—C7—N1—C8—N2) is a distorted envleope with Cremer & Pople (1975) puckering parameters Q, θ and φ of 0.4372 (17) Å, 121.2 (2)° and 129.4 (2)°, respectively (Fig. 1). For an ideal envelope conformation, θ and φ are 54.7° and (60n)°, respectively. The angle between the mean planes of the two coplanar 4-chlorophenyl groups is 58.9 (1)°. The angles between the mean planes of the benzyl group of the nonplanar, dihydroquinazolin-4 group and those of the two 4-chlorophenyl groups are 82.0 (6) and 84.3 (3)%, respectively. The torsion angles of the methylene amine linkage [N3–N2–C1–C2 = 159.78 (13)° and N3–C15–C16–C21 = -165.29 (16)°] indicates a significant twist between the dihydroquinazolin-4(1H)-one and attached 4-chlorophenyl group. Crystal packing is stabilized by intermolecular N1—H1A···O1 hydrogen bonding between nearby dihydroquinazolin groups which link the molecules into chains along the b axis of the unit cell (Fig.2).

Related literature top

For related structures, see: Shi et al. (2004a, 2004b); Shi, Li, Shi, Zhuang & Zhang (2004); Shi, Shi et al. (2004); Vembu et al. (2006); Swamy & Ravikumar (2005); Chruszcz et al. (2007). For related literature, see: Hodnett & Dunn (1970); Alaimo & Russel (1972); Alaimo & Hatton (1972); Cremer & Pople (1975); Misra et al. (1981); Varma et al. (1986); Singh & Dash (1988); Pandey et al. (1999); El-Masry et al. (2000); Desai et al. (2001); Birch et al. (2005).

Experimental top

A mixture of 2-aminobenzohydrazide (0.302 g, 0.002 mol) and 4-chlorobenzaldehyde (0.28 g, 0.002 mol) in 15 ml of absolute ethyl alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from a solvent mixture (8:2) of ethyl acetate and DMF (m.p.: 466–468 K). Analysis found: C 63.52, H 3.76, N 10.49%; C21H15Cl2N3O requires: C 63.65, H 3.82, N 10.60%.

Refinement top

The C—H atoms were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(c) using a riding model with C—H = 0.94 Å for aromatic and C—H = 0.99 Å for methine H atoms. The N—H H atom was located in difference map and was refined isotopic with varying coordinates. One chlorine atom is disordered in two positions and was refined anisotropic using a split model (s.o.f. = 0.143 (3) and 0.857 (3)).

Structure description top

Substituted 2,3-dihydroquinazolin-4(1H)-ones are found to be potent inhibitors of inosine 5'-monophosphate dehydrogenase type II (Birch et al., 2005) and also are found to possess antibacterial (Alaimo & Russel, 1972) and anthelmentic activities (Alaimo & Hatton, 1972). Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh & Dash, 1988; Varma et al., 1986), antitumor (Hodnett & Dunn, 1970., Misra et al., 1981; Desai et al., 2001), and also act as herbicides. The crystal structures of 3-(4-bromophenyl)-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Shi, Li, Shi, Zhuang & Zhang, 2004), 3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one (Shi et al., 2004a), 6-chloro-3-(4-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one acetone hemisolvate (Shi et al., 2004b), 7-chloro-2,2-dimethyl-3-(4-methylphenyl)-1,2-dihydroquinazolin-4(3H)-one (Shi, Shi et al., 2004), 2-(4-hydroxy-3-methoxyphenyl)-1-phenethyl-1,2-dihydroquinazolin-4(3H)-one (Swamy & Ravikumar, 2005), 5-chloro-3-hydroxy-2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one (Vembu et al., 2006) and 2-(biphenyl-4-yl)-2,3-dihydroquinazolin-4(1H)-one (Chruszcz et al., 2007) have been reported. A new quinazolinone containing Schiff base, C21H15Cl2N3O, has been synthesized and its crystal structure is reported. In our synthesis we expected the formation of 2-amino-N'-[(1E)-(4- chlorophenyl)methylene]benzohydrazide. Instead the aldehyde reacted with both primary amino groups and the cyclized form was created producing the title compound, (I).

The six-membered pyrimidin-4(1H)-one ring within the quinazoline group (C1—C2—C7—N1—C8—N2) is a distorted envleope with Cremer & Pople (1975) puckering parameters Q, θ and φ of 0.4372 (17) Å, 121.2 (2)° and 129.4 (2)°, respectively (Fig. 1). For an ideal envelope conformation, θ and φ are 54.7° and (60n)°, respectively. The angle between the mean planes of the two coplanar 4-chlorophenyl groups is 58.9 (1)°. The angles between the mean planes of the benzyl group of the nonplanar, dihydroquinazolin-4 group and those of the two 4-chlorophenyl groups are 82.0 (6) and 84.3 (3)%, respectively. The torsion angles of the methylene amine linkage [N3–N2–C1–C2 = 159.78 (13)° and N3–C15–C16–C21 = -165.29 (16)°] indicates a significant twist between the dihydroquinazolin-4(1H)-one and attached 4-chlorophenyl group. Crystal packing is stabilized by intermolecular N1—H1A···O1 hydrogen bonding between nearby dihydroquinazolin groups which link the molecules into chains along the b axis of the unit cell (Fig.2).

For related structures, see: Shi et al. (2004a, 2004b); Shi, Li, Shi, Zhuang & Zhang (2004); Shi, Shi et al. (2004); Vembu et al. (2006); Swamy & Ravikumar (2005); Chruszcz et al. (2007). For related literature, see: Hodnett & Dunn (1970); Alaimo & Russel (1972); Alaimo & Hatton (1972); Cremer & Pople (1975); Misra et al. (1981); Varma et al. (1986); Singh & Dash (1988); Pandey et al. (1999); El-Masry et al. (2000); Desai et al. (2001); Birch et al. (2005).

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram for C21H15Cl2N3O viewed down the a axis. Dashed lines indicate N—H···O intermolecular hydrogen bonds. Only the major component of the disordered chlorine atom (Cl2B) is displayed.
2-(4-Chlorophenyl)-3-{[(1E)-(4-chlorophenyl)methylene]amino}-2,3- dihydroquinazolin-4(1H)-one top
Crystal data top
C21H15Cl2N3OF(000) = 816
Mr = 396.26Dx = 1.372 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4254 reflections
a = 6.8774 (2) Åθ = 4.7–32.5°
b = 13.7315 (3) ŵ = 0.35 mm1
c = 20.4667 (8) ÅT = 203 K
β = 97.010 (3)°Plate, colorless
V = 1918.36 (10) Å30.53 × 0.47 × 0.13 mm
Z = 4
Data collection top
Oxford Diffraction Gemini
diffractometer
6303 independent reflections
Radiation source: fine-focus sealed tube2674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.5081 pixels mm-1θmax = 32.6°, θmin = 4.7°
φ and ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1820
Tmin = 0.926, Tmax = 1.000l = 2930
16112 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H atoms treated by a mixture of independent and constrained refinement
S = 1.63 w = 1/[σ2(Fo2) + (0.P)2]
where P = (Fo2 + 2Fc2)/3
6303 reflections(Δ/σ)max = 0.002
252 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C21H15Cl2N3OV = 1918.36 (10) Å3
Mr = 396.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.8774 (2) ŵ = 0.35 mm1
b = 13.7315 (3) ÅT = 203 K
c = 20.4667 (8) Å0.53 × 0.47 × 0.13 mm
β = 97.010 (3)°
Data collection top
Oxford Diffraction Gemini
diffractometer
6303 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2674 reflections with I > 2σ(I)
Tmin = 0.926, Tmax = 1.000Rint = 0.037
16112 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.055H atoms treated by a mixture of independent and constrained refinement
S = 1.63Δρmax = 0.42 e Å3
6303 reflectionsΔρmin = 0.40 e Å3
252 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. A disordered chlorine atom, Cl2A [(0.143 (3)] & Cl2B [0.857 (3)], occurs within the singly attached 4-chlorophenyl group to the dihydroquinazolin-4 ring and was refined so that their occupancies summed to 1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.10011 (6)0.67297 (3)1.01418 (2)0.06572 (16)
Cl2A0.2071 (12)0.0619 (3)0.9802 (4)0.0822 (5)0.143 (3)
Cl2B0.1030 (2)0.06077 (5)0.94734 (8)0.0822 (5)0.857 (3)
O10.65192 (12)0.52725 (6)0.74083 (5)0.0381 (3)
N10.74123 (16)0.23816 (9)0.75887 (6)0.0327 (3)
H1A0.7714 (16)0.1785 (9)0.7664 (6)0.034 (4)*
N20.59892 (14)0.38310 (7)0.79096 (6)0.0289 (3)
N30.51282 (17)0.43070 (8)0.84227 (6)0.0365 (3)
C10.68930 (18)0.43957 (10)0.74828 (7)0.0302 (4)
C20.83198 (18)0.38806 (9)0.71214 (7)0.0277 (3)
C30.94084 (19)0.43931 (10)0.67071 (7)0.0392 (4)
H3A0.92510.50710.66630.047*
C41.0717 (2)0.39151 (11)0.63603 (8)0.0461 (5)
H4A1.14770.42660.60890.055*
C51.09004 (19)0.29123 (11)0.64157 (8)0.0438 (4)
H5A1.17730.25830.61730.053*
C60.98294 (18)0.23944 (10)0.68187 (7)0.0366 (4)
H6A0.99650.17140.68490.044*
C70.85406 (18)0.28752 (9)0.71830 (7)0.0290 (3)
C80.68991 (19)0.28985 (9)0.81588 (8)0.0348 (4)
H8A0.80920.30310.84680.042*
C90.5468 (2)0.23071 (9)0.84980 (8)0.0311 (4)
C100.5939 (2)0.19858 (10)0.91276 (9)0.0454 (4)
H10A0.71850.21220.93510.055*
C110.4605 (3)0.14606 (11)0.94427 (9)0.0576 (5)
H11A0.49330.12470.98790.069*
C120.2817 (3)0.12593 (11)0.91110 (11)0.0555 (5)
C130.2316 (2)0.15577 (11)0.84789 (11)0.0562 (5)
H13A0.10780.14070.82540.067*
C140.3658 (2)0.20870 (10)0.81721 (8)0.0454 (4)
H14A0.33260.22980.77360.055*
C150.3577 (2)0.47659 (10)0.82277 (8)0.0366 (4)
H15A0.30950.47680.77780.044*
C160.2520 (2)0.52966 (9)0.86972 (8)0.0307 (4)
C170.3345 (2)0.54820 (10)0.93330 (8)0.0425 (4)
H17A0.46550.53040.94630.051*
C180.2287 (2)0.59239 (10)0.97826 (8)0.0448 (4)
H18A0.28600.60431.02160.054*
C190.0381 (2)0.61862 (10)0.95834 (9)0.0394 (4)
C200.0444 (2)0.60432 (11)0.89521 (9)0.0514 (5)
H20A0.17380.62450.88190.062*
C210.0633 (2)0.55979 (11)0.85062 (8)0.0464 (4)
H21A0.00670.55010.80690.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0652 (3)0.0591 (3)0.0796 (4)0.0083 (2)0.0364 (3)0.0211 (3)
Cl2A0.0861 (9)0.0506 (3)0.1259 (10)0.0030 (4)0.0771 (8)0.0145 (5)
Cl2B0.0861 (9)0.0506 (3)0.1259 (10)0.0030 (4)0.0771 (8)0.0145 (5)
O10.0502 (6)0.0192 (6)0.0473 (7)0.0034 (5)0.0154 (5)0.0021 (5)
N10.0446 (7)0.0153 (7)0.0414 (9)0.0031 (6)0.0183 (7)0.0006 (7)
N20.0390 (7)0.0177 (6)0.0323 (8)0.0055 (5)0.0138 (6)0.0015 (6)
N30.0462 (8)0.0272 (7)0.0388 (9)0.0043 (6)0.0159 (7)0.0001 (7)
C10.0365 (9)0.0222 (8)0.0316 (10)0.0041 (7)0.0034 (8)0.0022 (8)
C20.0347 (8)0.0186 (8)0.0310 (9)0.0002 (6)0.0090 (7)0.0011 (7)
C30.0552 (10)0.0225 (8)0.0429 (11)0.0029 (8)0.0178 (9)0.0002 (8)
C40.0635 (11)0.0322 (10)0.0486 (12)0.0055 (8)0.0310 (10)0.0003 (9)
C50.0521 (10)0.0361 (9)0.0483 (12)0.0003 (8)0.0257 (9)0.0045 (9)
C60.0470 (9)0.0213 (8)0.0446 (11)0.0027 (7)0.0179 (9)0.0018 (8)
C70.0330 (8)0.0233 (8)0.0317 (10)0.0019 (7)0.0083 (7)0.0002 (8)
C80.0403 (9)0.0241 (8)0.0418 (11)0.0034 (7)0.0121 (8)0.0034 (8)
C90.0378 (9)0.0201 (8)0.0373 (11)0.0029 (7)0.0125 (8)0.0003 (8)
C100.0588 (10)0.0349 (9)0.0422 (12)0.0011 (8)0.0043 (10)0.0027 (9)
C110.1026 (15)0.0367 (11)0.0379 (12)0.0006 (11)0.0270 (12)0.0049 (9)
C120.0733 (13)0.0266 (9)0.0777 (16)0.0010 (9)0.0538 (13)0.0019 (11)
C130.0358 (10)0.0399 (10)0.0956 (18)0.0014 (8)0.0192 (11)0.0007 (11)
C140.0478 (10)0.0373 (9)0.0516 (13)0.0035 (8)0.0075 (10)0.0085 (9)
C150.0431 (9)0.0319 (9)0.0359 (11)0.0035 (8)0.0090 (8)0.0034 (8)
C160.0362 (9)0.0239 (8)0.0330 (10)0.0025 (7)0.0083 (8)0.0005 (8)
C170.0409 (9)0.0441 (10)0.0429 (12)0.0172 (8)0.0069 (9)0.0032 (9)
C180.0499 (10)0.0464 (10)0.0380 (11)0.0103 (8)0.0054 (9)0.0061 (9)
C190.0425 (10)0.0282 (8)0.0507 (12)0.0036 (7)0.0181 (9)0.0056 (9)
C200.0324 (9)0.0636 (12)0.0584 (14)0.0069 (8)0.0060 (10)0.0090 (11)
C210.0392 (9)0.0562 (10)0.0433 (11)0.0010 (8)0.0030 (9)0.0110 (9)
Geometric parameters (Å, º) top
Cl1—C191.7410 (14)C8—H8A0.9900
Cl2A—C121.793 (6)C9—C101.3630 (19)
Cl2B—C121.7556 (17)C9—C141.3722 (18)
O1—C11.2367 (14)C10—C111.386 (2)
N1—C71.3815 (16)C10—H10A0.9400
N1—C81.4457 (17)C11—C121.359 (2)
N1—H1A0.854 (12)C11—H11A0.9400
N2—C11.3722 (16)C12—C131.361 (2)
N2—N31.4258 (14)C13—C141.384 (2)
N2—C81.4878 (15)C13—H13A0.9400
N3—C151.2610 (15)C14—H14A0.9400
C1—C21.4789 (17)C15—C161.4677 (18)
C2—C31.3892 (17)C15—H15A0.9400
C2—C71.3929 (17)C16—C211.3723 (17)
C3—C41.3786 (17)C16—C171.3786 (18)
C3—H3A0.9400C17—C181.3814 (18)
C4—C51.3862 (18)C17—H17A0.9400
C4—H4A0.9400C18—C191.3724 (18)
C5—C61.3699 (17)C18—H18A0.9400
C5—H5A0.9400C19—C201.361 (2)
C6—C71.3924 (16)C20—C211.3861 (19)
C6—H6A0.9400C20—H20A0.9400
C8—C91.5090 (17)C21—H21A0.9400
C7—N1—C8117.04 (12)C9—C10—H10A119.5
C7—N1—H1A115.9 (9)C11—C10—H10A119.5
C8—N1—H1A113.8 (9)C12—C11—C10118.91 (16)
C1—N2—N3118.10 (10)C12—C11—H11A120.5
C1—N2—C8120.02 (10)C10—C11—H11A120.5
N3—N2—C8109.70 (11)C11—C12—C13121.48 (16)
C15—N3—N2114.02 (13)C11—C12—Cl2B122.01 (18)
O1—C1—N2121.67 (12)C13—C12—Cl2B116.50 (18)
O1—C1—C2122.99 (13)C11—C12—Cl2A92.0 (3)
N2—C1—C2115.33 (12)C13—C12—Cl2A146.5 (4)
C3—C2—C7119.76 (12)Cl2B—C12—Cl2A30.1 (3)
C3—C2—C1120.20 (12)C12—C13—C14118.95 (17)
C7—C2—C1120.03 (13)C12—C13—H13A120.5
C4—C3—C2120.50 (13)C14—C13—H13A120.5
C4—C3—H3A119.7C9—C14—C13120.71 (16)
C2—C3—H3A119.7C9—C14—H14A119.6
C3—C4—C5119.29 (14)C13—C14—H14A119.6
C3—C4—H4A120.4N3—C15—C16120.56 (14)
C5—C4—H4A120.4N3—C15—H15A119.7
C6—C5—C4120.99 (14)C16—C15—H15A119.7
C6—C5—H5A119.5C21—C16—C17118.64 (14)
C4—C5—H5A119.5C21—C16—C15119.34 (15)
C5—C6—C7120.02 (13)C17—C16—C15121.99 (13)
C5—C6—H6A120.0C16—C17—C18121.34 (14)
C7—C6—H6A120.0C16—C17—H17A119.3
N1—C7—C6122.02 (12)C18—C17—H17A119.3
N1—C7—C2118.53 (12)C19—C18—C17118.64 (15)
C6—C7—C2119.41 (13)C19—C18—H18A120.7
N1—C8—N2106.24 (12)C17—C18—H18A120.7
N1—C8—C9110.14 (11)C20—C19—C18121.11 (15)
N2—C8—C9110.50 (10)C20—C19—Cl1119.17 (13)
N1—C8—H8A110.0C18—C19—Cl1119.71 (14)
N2—C8—H8A110.0C19—C20—C21119.64 (15)
C9—C8—H8A110.0C19—C20—H20A120.2
C10—C9—C14119.02 (14)C21—C20—H20A120.2
C10—C9—C8121.07 (14)C16—C21—C20120.54 (16)
C14—C9—C8119.92 (14)C16—C21—H21A119.7
C9—C10—C11120.92 (16)C20—C21—H21A119.7
C1—N2—N3—C1572.35 (15)N1—C8—C9—C10117.64 (15)
C8—N2—N3—C15145.13 (11)N2—C8—C9—C10125.28 (14)
N3—N2—C1—O120.85 (19)N1—C8—C9—C1462.48 (16)
C8—N2—C1—O1159.42 (13)N2—C8—C9—C1454.59 (17)
N3—N2—C1—C2159.47 (11)C14—C9—C10—C111.3 (2)
C8—N2—C1—C220.89 (18)C8—C9—C10—C11178.60 (13)
O1—C1—C2—C34.3 (2)C9—C10—C11—C120.7 (2)
N2—C1—C2—C3176.04 (12)C10—C11—C12—C130.3 (2)
O1—C1—C2—C7174.11 (13)C10—C11—C12—Cl2B179.45 (11)
N2—C1—C2—C75.58 (19)C10—C11—C12—Cl2A179.9 (2)
C7—C2—C3—C40.5 (2)C11—C12—C13—C140.7 (2)
C1—C2—C3—C4178.91 (13)Cl2B—C12—C13—C14179.05 (11)
C2—C3—C4—C51.7 (2)Cl2A—C12—C13—C14180.0 (3)
C3—C4—C5—C61.2 (2)C10—C9—C14—C130.8 (2)
C4—C5—C6—C70.3 (2)C8—C9—C14—C13179.04 (12)
C8—N1—C7—C6150.60 (13)C12—C13—C14—C90.1 (2)
C8—N1—C7—C231.76 (19)N2—N3—C15—C16179.84 (11)
C5—C6—C7—N1179.12 (13)N3—C15—C16—C21165.09 (13)
C5—C6—C7—C21.5 (2)N3—C15—C16—C1713.2 (2)
C3—C2—C7—N1178.77 (13)C21—C16—C17—C182.7 (2)
C1—C2—C7—N10.4 (2)C15—C16—C17—C18175.57 (13)
C3—C2—C7—C61.1 (2)C16—C17—C18—C190.5 (2)
C1—C2—C7—C6177.32 (13)C17—C18—C19—C201.9 (2)
C7—N1—C8—N253.23 (15)C17—C18—C19—Cl1179.14 (11)
C7—N1—C8—C9172.93 (12)C18—C19—C20—C212.0 (2)
C1—N2—C8—N148.54 (15)Cl1—C19—C20—C21179.03 (12)
N3—N2—C8—N1169.77 (10)C17—C16—C21—C202.6 (2)
C1—N2—C8—C9168.00 (13)C15—C16—C21—C20175.72 (14)
N3—N2—C8—C950.31 (15)C19—C20—C21—C160.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.854 (12)2.153 (13)2.9877 (15)165.7 (12)
Symmetry code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC21H15Cl2N3O
Mr396.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)203
a, b, c (Å)6.8774 (2), 13.7315 (3), 20.4667 (8)
β (°) 97.010 (3)
V3)1918.36 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.53 × 0.47 × 0.13
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.926, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16112, 6303, 2674
Rint0.037
(sin θ/λ)max1)0.757
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.055, 1.63
No. of reflections6303
No. of parameters252
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.40

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.854 (12)2.153 (13)2.9877 (15)165.7 (12)
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

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