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In the title compound, C22H18Cl2N2, the seven-membered heterocyclic ring is in a boat-shaped conformation. The mol­ecules are linked by N—H...N hydrogen bonding into one-dimensional chains along the [010] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029066/nc2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029066/nc2040Isup2.hkl
Contains datablock I

CCDC reference: 621740

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.097
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

1,5-benzodiazepine derivatives have been attracting great interest because of their potential pharmacological use as hypnotic agents (Landquist et al., 1984; Schutz et al., 1982), against cancer (Atwal et al., 1987; Merluzzi et al., 1990), viral infections (Merluzzi et al., 1990) and cardiovascular disorders (Di Braccio et al., 2001; Tranquillini et al., 1997). They are also of interest in the development of new classes of fused heterocyclic compounds, as exemplified by triazolo- (Aversa et al., 1986), oxadiazolo-(Chimirri et al., 1990), oxazino- (El-Sayed et al., 1999) or furanobenzodiazepines (Reddy et al., 2000). A literature search for 1,5-benzodiazepines substituted at C7 and C9 leads to (2-(4- Nitro-phenyl)-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine) (Braun et al., 2000), (2,4-Bis-(2,5-dipropoxy-phenyl) -2,3-dihydro-1H-1,5-benzodiazepine) (Hormaza et al., 2004), 4,5:15,16-Dibenzo-2,7:13,18-dimethano-7,13-dimethyl-3,6,14, 17,23,24-hexa-azatricyclo(17.3.1.18,12) tetracosa-1(23),2,8, 11,12 (24),17,19,21-octaene (V) (de O. Cabral et al., 1982) and (VI) (4-(4-Methoxy-phenyl)-2-(4-nitro-phenyl)-2,3-dihydro- 1H-1,5-benzodiazepine) (Braun et al., 2004), which are related to the title compound. In view of the importance of such compounds we have determined the structure of the title compound (I).

In the crystal structure of the title compound (I) the seven-membered heterocyclic is in an boat-shaped conformation with an approximate mirror plane through C8 and the mid-point of the C1—C2 bond (Fig. 1). A similar boat structure is also observed in 1-Benzyl-4-(4-nitrophenyl)-2,3-dihydro-1H-1,5-benzodiazepine (Low et al., 2003) and 2,2,4-Trimethyl-2,3-dihydro-1H- 1,5-benzodiazepine (Samanta et al., 1999). The atoms N1 and N2 are not coplanar with the adjacent aryl ring, as shown both by the N1—C1—C2—N2 torsion angle (4.1 (3) °), and by the deviations of the two N atoms (-0.015 (1) Å for N1 and -0.154 (2) Å for N2) from the plane of the aryl ring (C1/C2/C3/C4/C5/C6).

The phenyl rings C10 to C15 and C16 to C21 are rotated out of the plane of the seven membered ring, which is probably due to the steric affects of the phenyl groups. This phenomenon is also found in 2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiaze-pine (Kaluski et al., 1989).

The molecules are connected via intermolecular N—H···N hydrogen bonding between N2 which act as a donor and the H atom attached to N1 into chains that elongate in the [010] direction (Fig. 2).

Related literature top

For related structures see: Braun et al. (2000); Hormaza et al. (2004); Cabral et al. (1982); Braun & Muller (2004); Samanta et al. (1999); Kaluski et al. (1989). For related literature, see: Atwal et al. (1987); Aversa et al. (1986); Chimirri et al. (1990); Di Braccio, Grossi, Roma, Vargiu, Mura & Marongiu (2001); El-Sayed, Abdel-Ghany, Saghier & El (1999); Kaluski et al. (1989); Landquist (1984); Low et al. (2003); Merluzzi et al. (1990); Reddy et al. (2000); Schutz (1982); Tranquillini et al. (1997); Samanta (1999).

Experimental top

Phenylenediamine (0.11 g, 1.0 mmol), montmorillonite K10 (0.3 g) and 4-chloroacetophenone (0.34 g, 2.2 mmol) were mixed and afterwards allowed to stay at room temperature for 24 h. On completion of the reaction, which was monitored by TLC, montmorillonite was filtered off and washed with 3.5 ml of acetone. The filtrate was evaporated to dryness and the residue was subjected to column chromatography over silica gel using petroleum ether-acetone (4:1) as eluent to afford compound I in 87% yield (0.33 g). The crystal was obtained by evaporation of the solvent from a solution of I in acetone-petroleum ether (1:1).1H NMR (CDCl3, 400 MHz): δ 1.74 (s, 3H, CH3), 2.88 (d, 1H, J=12.8 Hz), 3.07 (d, 1H, J=12 Hz), 3.43 (s, 1H, NH), 6.84–7.53 (m, 12H, ArH). 13C NMR (CDCl3, 100 MHz): δ 30.2, 43.3, 74.1, 122.0, 122.5, 127.1, 127.5, 128.7, 128.8, 129.0, 133.4, 136.5, 138.0, 140.3, 146.2, 166.6. UV λmax (EtOH): 262 nm, 365 nm. IR (KBr, cm-1): 3272 (s), 1590 (m), 1559(m), 1474(s), 1436(w), 1397(m), 1328(m), 1243(s), 1212(m), 1096(m), 1011(m).

Refinement top

C—H atoms were positioned with idealized geometry and were refined isotropic using a riding model with C—H = 0.94 Å for aromatic, C—H = 0.98 Å for methylene and C—H = 0.97 Å for methy H atoms and Uiso(H)=1.2Ueq(C) for aromatic and methylene H atoms and Uiso(H)=1.5Ueq(C) for methyl H atoms. The N—H H atom was located in difference map and was refined isotropic (Uiso(H)=1.2Ueq(N) with the N—H bond length restraint to 0.83 (2) Å.

Structure description top

1,5-benzodiazepine derivatives have been attracting great interest because of their potential pharmacological use as hypnotic agents (Landquist et al., 1984; Schutz et al., 1982), against cancer (Atwal et al., 1987; Merluzzi et al., 1990), viral infections (Merluzzi et al., 1990) and cardiovascular disorders (Di Braccio et al., 2001; Tranquillini et al., 1997). They are also of interest in the development of new classes of fused heterocyclic compounds, as exemplified by triazolo- (Aversa et al., 1986), oxadiazolo-(Chimirri et al., 1990), oxazino- (El-Sayed et al., 1999) or furanobenzodiazepines (Reddy et al., 2000). A literature search for 1,5-benzodiazepines substituted at C7 and C9 leads to (2-(4- Nitro-phenyl)-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine) (Braun et al., 2000), (2,4-Bis-(2,5-dipropoxy-phenyl) -2,3-dihydro-1H-1,5-benzodiazepine) (Hormaza et al., 2004), 4,5:15,16-Dibenzo-2,7:13,18-dimethano-7,13-dimethyl-3,6,14, 17,23,24-hexa-azatricyclo(17.3.1.18,12) tetracosa-1(23),2,8, 11,12 (24),17,19,21-octaene (V) (de O. Cabral et al., 1982) and (VI) (4-(4-Methoxy-phenyl)-2-(4-nitro-phenyl)-2,3-dihydro- 1H-1,5-benzodiazepine) (Braun et al., 2004), which are related to the title compound. In view of the importance of such compounds we have determined the structure of the title compound (I).

In the crystal structure of the title compound (I) the seven-membered heterocyclic is in an boat-shaped conformation with an approximate mirror plane through C8 and the mid-point of the C1—C2 bond (Fig. 1). A similar boat structure is also observed in 1-Benzyl-4-(4-nitrophenyl)-2,3-dihydro-1H-1,5-benzodiazepine (Low et al., 2003) and 2,2,4-Trimethyl-2,3-dihydro-1H- 1,5-benzodiazepine (Samanta et al., 1999). The atoms N1 and N2 are not coplanar with the adjacent aryl ring, as shown both by the N1—C1—C2—N2 torsion angle (4.1 (3) °), and by the deviations of the two N atoms (-0.015 (1) Å for N1 and -0.154 (2) Å for N2) from the plane of the aryl ring (C1/C2/C3/C4/C5/C6).

The phenyl rings C10 to C15 and C16 to C21 are rotated out of the plane of the seven membered ring, which is probably due to the steric affects of the phenyl groups. This phenomenon is also found in 2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiaze-pine (Kaluski et al., 1989).

The molecules are connected via intermolecular N—H···N hydrogen bonding between N2 which act as a donor and the H atom attached to N1 into chains that elongate in the [010] direction (Fig. 2).

For related structures see: Braun et al. (2000); Hormaza et al. (2004); Cabral et al. (1982); Braun & Muller (2004); Samanta et al. (1999); Kaluski et al. (1989). For related literature, see: Atwal et al. (1987); Aversa et al. (1986); Chimirri et al. (1990); Di Braccio, Grossi, Roma, Vargiu, Mura & Marongiu (2001); El-Sayed, Abdel-Ghany, Saghier & El (1999); Kaluski et al. (1989); Landquist (1984); Low et al. (2003); Merluzzi et al. (1990); Reddy et al. (2000); Schutz (1982); Tranquillini et al. (1997); Samanta (1999).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Crystal structure of compound (I) with labelling and displacement elipsoid drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal structure of compound(I) with view in the direction of the c axis (N—H···N hydrogen bonding is shown as dashed lines).
2,4-Bis(4-chlorophenyl)-2-methyl-2,3-dihydro-1H-1,5-benzodiazepine top
Crystal data top
C22H18Cl2N2F(000) = 792
Mr = 381.28Dx = 1.356 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 6453 reflections
a = 14.095 (3) Åθ = 3.1–25.3°
b = 9.9845 (15) ŵ = 0.36 mm1
c = 14.859 (3) ÅT = 213 K
β = 116.728 (3)°Block, yellow
V = 1867.7 (6) Å30.48 × 0.38 × 0.20 mm
Z = 4
Data collection top
Rigaku Mercury
diffractometer
3404 independent reflections
Radiation source: fine-focus sealed tube3103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 7.31 pixels mm-1θmax = 25.4°, θmin = 3.1°
ω scansh = 1616
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1212
Tmin = 0.834, Tmax = 0.921l = 1716
17639 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0374P)2 + 0.8045P]
where P = (Fo2 + 2Fc2)/3
3404 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C22H18Cl2N2V = 1867.7 (6) Å3
Mr = 381.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.095 (3) ŵ = 0.36 mm1
b = 9.9845 (15) ÅT = 213 K
c = 14.859 (3) Å0.48 × 0.38 × 0.20 mm
β = 116.728 (3)°
Data collection top
Rigaku Mercury
diffractometer
3404 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
3103 reflections with I > 2σ(I)
Tmin = 0.834, Tmax = 0.921Rint = 0.028
17639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.20 e Å3
3404 reflectionsΔρmin = 0.32 e Å3
241 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
Cl10.45977 (4)0.38308 (5)0.58336 (4)0.05107 (17)
Cl20.49691 (4)0.97041 (7)0.31844 (4)0.0594 (2)
N10.00610 (12)0.71966 (15)0.37243 (11)0.0301 (3)
N20.00367 (12)0.97254 (17)0.27959 (12)0.0315 (4)
H20.0114 (17)1.033 (2)0.2376 (18)0.041 (6)*
C10.08515 (14)0.80205 (18)0.33118 (13)0.0296 (4)
C20.08722 (14)0.92813 (19)0.28826 (13)0.0312 (4)
C30.18201 (16)0.9998 (2)0.24741 (15)0.0409 (5)
H30.18441.08460.21890.049*
C40.27317 (16)0.9482 (2)0.24808 (16)0.0476 (5)
H40.33620.99860.22100.057*
C50.27147 (16)0.8233 (2)0.28832 (16)0.0453 (5)
H50.33320.78830.28870.054*
C60.17828 (15)0.7497 (2)0.32819 (14)0.0369 (4)
H60.17770.66340.35360.044*
C70.09696 (14)0.77208 (18)0.42989 (13)0.0281 (4)
C80.10919 (14)0.91792 (17)0.45824 (13)0.0286 (4)
H8A0.17950.93150.51510.034*
H8B0.05610.94130.48120.034*
C90.09695 (14)1.01437 (18)0.37237 (13)0.0287 (4)
C100.18912 (14)0.67966 (18)0.47382 (12)0.0281 (4)
C110.17155 (15)0.54254 (19)0.47762 (14)0.0330 (4)
H110.10200.51070.45620.040*
C120.25524 (15)0.45329 (19)0.51245 (14)0.0361 (4)
H120.24260.36120.51450.043*
C130.35711 (15)0.49938 (19)0.54418 (14)0.0347 (4)
C140.37761 (15)0.6339 (2)0.54494 (15)0.0387 (5)
H140.44780.66480.56900.046*
C150.29383 (15)0.72347 (19)0.50997 (14)0.0349 (4)
H150.30770.81560.51060.042*
C160.19604 (15)1.00558 (17)0.35502 (13)0.0298 (4)
C170.20002 (16)0.9223 (2)0.28171 (14)0.0357 (4)
H170.13930.87350.23910.043*
C180.29232 (17)0.9102 (2)0.27055 (15)0.0411 (5)
H180.29440.85270.22130.049*
C190.38053 (16)0.9830 (2)0.33215 (15)0.0383 (5)
C200.37924 (16)1.0662 (2)0.40541 (15)0.0391 (5)
H200.44011.11540.44730.047*
C210.28728 (15)1.07658 (19)0.41658 (14)0.0351 (4)
H210.28641.13290.46690.042*
C220.07973 (16)1.15650 (19)0.40215 (15)0.0358 (4)
H22A0.08431.22070.35530.054*
H22B0.13391.17630.46980.054*
H22C0.01011.16210.40020.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0413 (3)0.0425 (3)0.0614 (4)0.0102 (2)0.0160 (3)0.0041 (2)
Cl20.0425 (3)0.0919 (5)0.0528 (4)0.0102 (3)0.0294 (3)0.0096 (3)
N10.0302 (8)0.0306 (8)0.0304 (8)0.0029 (7)0.0143 (7)0.0013 (6)
N20.0355 (9)0.0345 (9)0.0247 (8)0.0000 (7)0.0136 (7)0.0030 (7)
C10.0294 (9)0.0332 (10)0.0263 (9)0.0017 (8)0.0126 (7)0.0062 (7)
C20.0322 (10)0.0382 (10)0.0239 (9)0.0013 (8)0.0132 (8)0.0032 (8)
C30.0412 (12)0.0471 (12)0.0336 (11)0.0102 (9)0.0161 (9)0.0033 (9)
C40.0316 (11)0.0665 (15)0.0417 (12)0.0116 (10)0.0138 (9)0.0004 (11)
C50.0319 (11)0.0618 (14)0.0450 (12)0.0034 (10)0.0198 (9)0.0064 (10)
C60.0353 (11)0.0427 (11)0.0345 (10)0.0050 (9)0.0174 (8)0.0057 (8)
C70.0319 (10)0.0311 (10)0.0249 (9)0.0026 (8)0.0161 (8)0.0013 (7)
C80.0334 (10)0.0286 (9)0.0251 (9)0.0013 (8)0.0145 (8)0.0017 (7)
C90.0353 (10)0.0274 (9)0.0255 (9)0.0031 (8)0.0155 (8)0.0021 (7)
C100.0331 (9)0.0286 (9)0.0233 (9)0.0034 (8)0.0133 (7)0.0010 (7)
C110.0329 (10)0.0312 (10)0.0337 (10)0.0052 (8)0.0141 (8)0.0000 (8)
C120.0409 (11)0.0282 (10)0.0375 (11)0.0027 (8)0.0161 (9)0.0003 (8)
C130.0342 (10)0.0366 (11)0.0322 (10)0.0037 (8)0.0139 (8)0.0005 (8)
C140.0288 (10)0.0383 (11)0.0471 (12)0.0041 (8)0.0153 (9)0.0001 (9)
C150.0368 (11)0.0289 (10)0.0382 (11)0.0052 (8)0.0163 (9)0.0001 (8)
C160.0381 (10)0.0250 (9)0.0291 (9)0.0005 (8)0.0177 (8)0.0031 (7)
C170.0398 (11)0.0367 (11)0.0332 (10)0.0024 (9)0.0187 (9)0.0033 (8)
C180.0470 (12)0.0477 (12)0.0347 (11)0.0060 (10)0.0237 (9)0.0025 (9)
C190.0367 (11)0.0463 (12)0.0367 (11)0.0072 (9)0.0207 (9)0.0109 (9)
C200.0360 (11)0.0371 (11)0.0415 (11)0.0017 (9)0.0150 (9)0.0030 (9)
C210.0398 (11)0.0310 (10)0.0355 (10)0.0017 (8)0.0178 (9)0.0044 (8)
C220.0453 (11)0.0288 (10)0.0394 (11)0.0010 (8)0.0244 (9)0.0011 (8)
Geometric parameters (Å, º) top
Cl1—C131.7387 (19)C10—C151.395 (3)
Cl2—C191.746 (2)C10—C111.397 (3)
N1—C71.288 (2)C11—C121.380 (3)
N1—C11.413 (2)C11—H110.9400
N2—C21.415 (2)C12—C131.374 (3)
N2—C91.474 (2)C12—H120.9400
N2—H20.83 (2)C13—C141.373 (3)
C1—C61.395 (3)C14—C151.383 (3)
C1—C21.405 (3)C14—H140.9400
C2—C31.392 (3)C15—H150.9400
C3—C41.389 (3)C16—C211.391 (3)
C3—H30.9400C16—C171.391 (3)
C4—C51.379 (3)C17—C181.389 (3)
C4—H40.9400C17—H170.9400
C5—C61.384 (3)C18—C191.374 (3)
C5—H50.9400C18—H180.9400
C6—H60.9400C19—C201.376 (3)
C7—C101.484 (3)C20—C211.383 (3)
C7—C81.504 (2)C20—H200.9400
C8—C91.545 (2)C21—H210.9400
C8—H8A0.9800C22—H22A0.9700
C8—H8B0.9800C22—H22B0.9700
C9—C161.533 (2)C22—H22C0.9700
C9—C221.538 (3)
C7—N1—C1119.37 (15)C12—C11—C10120.72 (17)
C2—N2—C9117.82 (14)C12—C11—H11119.6
C2—N2—H2111.2 (15)C10—C11—H11119.6
C9—N2—H2108.5 (15)C13—C12—C11119.85 (18)
C6—C1—C2119.58 (17)C13—C12—H12120.1
C6—C1—N1117.11 (17)C11—C12—H12120.1
C2—C1—N1123.18 (16)C14—C13—C12120.95 (18)
C3—C2—C1118.60 (18)C14—C13—Cl1120.68 (15)
C3—C2—N2122.00 (18)C12—C13—Cl1118.37 (15)
C1—C2—N2119.14 (16)C13—C14—C15119.25 (18)
C4—C3—C2121.1 (2)C13—C14—H14120.4
C4—C3—H3119.5C15—C14—H14120.4
C2—C3—H3119.5C14—C15—C10121.25 (17)
C5—C4—C3120.2 (2)C14—C15—H15119.4
C5—C4—H4119.9C10—C15—H15119.4
C3—C4—H4119.9C21—C16—C17117.94 (17)
C4—C5—C6119.57 (19)C21—C16—C9120.21 (16)
C4—C5—H5120.2C17—C16—C9121.77 (16)
C6—C5—H5120.2C18—C17—C16121.03 (18)
C5—C6—C1120.9 (2)C18—C17—H17119.5
C5—C6—H6119.6C16—C17—H17119.5
C1—C6—H6119.6C19—C18—C17119.32 (18)
N1—C7—C10116.84 (16)C19—C18—H18120.3
N1—C7—C8122.24 (16)C17—C18—H18120.3
C10—C7—C8120.76 (15)C18—C19—C20121.10 (18)
C7—C8—C9114.58 (14)C18—C19—Cl2120.02 (16)
C7—C8—H8A108.6C20—C19—Cl2118.88 (16)
C9—C8—H8A108.6C19—C20—C21119.11 (19)
C7—C8—H8B108.6C19—C20—H20120.4
C9—C8—H8B108.6C21—C20—H20120.4
H8A—C8—H8B107.6C20—C21—C16121.49 (18)
N2—C9—C16108.87 (14)C20—C21—H21119.3
N2—C9—C22109.92 (15)C16—C21—H21119.3
C16—C9—C22112.02 (15)C9—C22—H22A109.5
N2—C9—C8108.48 (14)C9—C22—H22B109.5
C16—C9—C8109.36 (14)H22A—C22—H22B109.5
C22—C9—C8108.12 (14)C9—C22—H22C109.5
C15—C10—C11117.90 (17)H22A—C22—H22C109.5
C15—C10—C7122.66 (16)H22B—C22—H22C109.5
C11—C10—C7119.42 (16)
C7—N1—C1—C6139.58 (17)C8—C7—C10—C11156.48 (16)
C7—N1—C1—C244.5 (2)C15—C10—C11—C122.5 (3)
C6—C1—C2—C32.6 (3)C7—C10—C11—C12176.09 (16)
N1—C1—C2—C3178.39 (16)C10—C11—C12—C130.3 (3)
C6—C1—C2—N2171.65 (16)C11—C12—C13—C142.2 (3)
N1—C1—C2—N24.1 (3)C11—C12—C13—Cl1177.79 (15)
C9—N2—C2—C3112.9 (2)C12—C13—C14—C152.2 (3)
C9—N2—C2—C173.0 (2)Cl1—C13—C14—C15177.73 (15)
C1—C2—C3—C40.4 (3)C13—C14—C15—C100.1 (3)
N2—C2—C3—C4173.62 (18)C11—C10—C15—C142.4 (3)
C2—C3—C4—C50.9 (3)C7—C10—C15—C14176.10 (17)
C3—C4—C5—C60.1 (3)N2—C9—C16—C21160.02 (16)
C4—C5—C6—C12.1 (3)C22—C9—C16—C2138.2 (2)
C2—C1—C6—C53.5 (3)C8—C9—C16—C2181.6 (2)
N1—C1—C6—C5179.51 (16)N2—C9—C16—C1723.3 (2)
C1—N1—C7—C10177.88 (14)C22—C9—C16—C17145.10 (17)
C1—N1—C7—C82.4 (2)C8—C9—C16—C1795.1 (2)
N1—C7—C8—C973.0 (2)C21—C16—C17—C180.2 (3)
C10—C7—C8—C9111.68 (18)C9—C16—C17—C18176.54 (17)
C2—N2—C9—C16158.23 (15)C16—C17—C18—C190.8 (3)
C2—N2—C9—C2278.7 (2)C17—C18—C19—C200.8 (3)
C2—N2—C9—C839.3 (2)C17—C18—C19—Cl2179.33 (15)
C7—C8—C9—N245.0 (2)C18—C19—C20—C210.2 (3)
C7—C8—C9—C1673.60 (19)Cl2—C19—C20—C21179.98 (15)
C7—C8—C9—C22164.18 (15)C19—C20—C21—C160.5 (3)
N1—C7—C10—C15159.47 (16)C17—C16—C21—C200.5 (3)
C8—C7—C10—C1525.0 (2)C9—C16—C21—C20177.27 (17)
N1—C7—C10—C1119.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.83 (2)2.50 (2)3.306 (2)165 (2)
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H18Cl2N2
Mr381.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)213
a, b, c (Å)14.095 (3), 9.9845 (15), 14.859 (3)
β (°) 116.728 (3)
V3)1867.7 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.48 × 0.38 × 0.20
Data collection
DiffractometerRigaku Mercury
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.834, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections
17639, 3404, 3103
Rint0.028
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.097, 1.14
No. of reflections3404
No. of parameters241
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.32

Computer programs: CrystalClear (Rigaku/MSC, 2001), CrystalClear, CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
N1—C11.413 (2)N2—C21.415 (2)
N1—C1—C2—N24.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.83 (2)2.50 (2)3.306 (2)165 (2)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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