2-(2-Chloro-phen-yl)-3-methyl-5,6-diphenyl-2,3-dihydro-pyrazine.

In the title mol-ecule, C(23)H(19)ClN(2), the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The benzene ring at position 2 makes dihedral angles of 77.88 (12) and 76.31 (12)° with the phenyl rings at positions 5 and 6, respectively. The dihedral angle between the phenyl rings at positions 5 and 6 is 70.05 (10)°. The Cl atom is disordered over two positions with occupancy factors of 0.946 (5) and 0.054 (5). In the crystal, C-H⋯π inter-actions are found.

Related literature

For the biological properties of heterocyclic ring systems having a dihydro­pyrazine nucleus, see: Sondhi et al. (2005 ▶). For the use of dihydro­pyrazines, with reference to DNA breakage activity, see: Takechi et al. (2011 ▶). For the inhibition of the growth of Escherichia coli, see: Takeda et al. (2005 ▶). For a closely related crystal structure, see: Anuradha et al. (2009 ▶).

Experimental

Crystal data

C23H19ClN2

M = 358.85

Monoclinic,

a = 10.5675 (8) Å

b = 19.7014 (9) Å

c = 10.4207 (7) Å

β = 118.479 (9)°

V = 1907.0 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.82 mm−1

T = 298 K

0.25 × 0.14 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.659, T max = 1.000

22812 measured reflections

3831 independent reflections

3092 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.150

S = 1.04

3831 reflections

240 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036336/wn2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036336/wn2451Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036336/wn2451Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19ClN2	F(000) = 752
Mr = 358.85	Dx = 1.250 Mg m−3
Monoclinic, P21/c	Melting point: 417 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 10.5675 (8) Å	Cell parameters from 5083 reflections
b = 19.7014 (9) Å	θ = 4.5–73.5°
c = 10.4207 (7) Å	µ = 1.82 mm−1
β = 118.479 (9)°	T = 298 K
V = 1907.0 (3) Å3	Block, pale-yellow
Z = 4	0.25 × 0.14 × 0.10 mm

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3831 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3092 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 16.1500 pixels mm-1	θmax = 73.7°, θmin = 4.5°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −21→24
Tmin = 0.659, Tmax = 1.000	l = −12→12
22812 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.4958P] where P = (Fo2 + 2Fc2)/3
3831 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.32 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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.To allow for a stable and meaningful refinement of the Cl atoms, the C—Cl bonding distances were restrained to be the same (DFIX 1.76 0.02 C22 Cl1 C22 Cl2 and EADP Cl1 Cl2).

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.25340 (11)	−0.21842 (8)	0.16414 (14)	0.1246 (4)	0.946 (5)
N1	0.24840 (17)	−0.00156 (8)	0.13885 (16)	0.0488 (5)
N4	0.2879 (2)	−0.02095 (9)	−0.10830 (18)	0.0627 (6)
C2	0.3045 (2)	−0.06586 (10)	0.1173 (2)	0.0556 (6)
C3	0.3806 (3)	−0.05552 (12)	0.0291 (3)	0.0657 (8)
C5	0.2014 (2)	0.02435 (9)	−0.10666 (19)	0.0479 (5)
C6	0.20118 (18)	0.04090 (9)	0.03284 (18)	0.0439 (5)
C21	0.3972 (2)	−0.09884 (10)	0.2638 (2)	0.0527 (6)
C22	0.3840 (3)	−0.16562 (12)	0.2953 (3)	0.0698 (7)
C23	0.4712 (3)	−0.19357 (14)	0.4313 (3)	0.0861 (9)
C24	0.5737 (3)	−0.15478 (14)	0.5392 (3)	0.0767 (8)
C25	0.5914 (3)	−0.08844 (13)	0.5117 (2)	0.0664 (7)
C26	0.5037 (2)	−0.06128 (10)	0.3758 (2)	0.0571 (6)
C31	0.4413 (3)	−0.11844 (14)	−0.0028 (3)	0.0828 (10)
C51	0.1010 (2)	0.05635 (9)	−0.24852 (19)	0.0474 (5)
C52	−0.0386 (2)	0.07317 (11)	−0.2826 (2)	0.0562 (6)
C53	−0.1342 (3)	0.09626 (12)	−0.4219 (2)	0.0664 (7)
C54	−0.0896 (3)	0.10359 (11)	−0.5258 (2)	0.0682 (8)
C55	0.0493 (3)	0.08806 (11)	−0.4913 (2)	0.0650 (8)
C56	0.1443 (2)	0.06438 (10)	−0.3546 (2)	0.0552 (6)
C61	0.15526 (19)	0.10853 (9)	0.05924 (18)	0.0441 (5)
C62	0.0827 (2)	0.11347 (9)	0.14084 (19)	0.0478 (5)
C63	0.0489 (2)	0.17630 (11)	0.1757 (2)	0.0568 (6)
C64	0.0894 (3)	0.23491 (10)	0.1328 (2)	0.0619 (7)
C65	0.1610 (3)	0.23089 (10)	0.0524 (2)	0.0638 (7)
C66	0.1926 (2)	0.16820 (10)	0.0139 (2)	0.0563 (6)
Cl2	0.249 (2)	−0.1906 (15)	0.131 (2)	0.1246 (4)	0.054 (5)
H2	0.22221	−0.09585	0.06166	0.0668*
H3	0.46199	−0.02520	0.08554	0.0789*
H23	0.45990	−0.23883	0.44909	0.1033*
H24	0.63129	−0.17328	0.63114	0.0921*
H25	0.66209	−0.06190	0.58423	0.0797*
H26	0.51645	−0.01613	0.35854	0.0686*
H31A	0.36507	−0.15035	−0.05490	0.1243*
H31B	0.51148	−0.13840	0.08724	0.1243*
H31C	0.48607	−0.10673	−0.06119	0.1243*
H52	−0.06864	0.06904	−0.21230	0.0674*
H53	−0.22846	0.10679	−0.44500	0.0797*
H54	−0.15360	0.11902	−0.61885	0.0818*
H55	0.07976	0.09357	−0.56100	0.0780*
H56	0.23810	0.05365	−0.33281	0.0662*
H62	0.05680	0.07420	0.17213	0.0574*
H63	−0.00147	0.17897	0.22840	0.0682*
H64	0.06832	0.27704	0.15826	0.0743*
H65	0.18848	0.27043	0.02348	0.0765*
H66	0.23901	0.16601	−0.04263	0.0676*

	U11	U22	U33	U12	U13	U23
Cl1	0.1170 (7)	0.0679 (8)	0.1060 (7)	−0.0285 (5)	−0.0141 (5)	0.0118 (5)
N1	0.0561 (9)	0.0475 (8)	0.0414 (7)	0.0091 (7)	0.0221 (7)	0.0047 (6)
N4	0.0780 (12)	0.0660 (11)	0.0473 (9)	0.0211 (9)	0.0324 (9)	0.0053 (8)
C2	0.0608 (11)	0.0550 (11)	0.0456 (10)	0.0144 (9)	0.0209 (9)	0.0056 (8)
C3	0.0808 (14)	0.0633 (13)	0.0593 (12)	0.0228 (11)	0.0384 (11)	0.0090 (9)
C5	0.0557 (10)	0.0474 (9)	0.0414 (9)	0.0020 (8)	0.0239 (8)	0.0012 (7)
C6	0.0445 (8)	0.0467 (9)	0.0393 (8)	0.0013 (7)	0.0189 (7)	0.0023 (7)
C21	0.0556 (10)	0.0504 (10)	0.0464 (10)	0.0127 (8)	0.0198 (8)	0.0053 (8)
C22	0.0627 (12)	0.0561 (12)	0.0651 (13)	0.0016 (10)	0.0098 (10)	0.0082 (10)
C23	0.0831 (17)	0.0629 (14)	0.0829 (17)	0.0048 (12)	0.0158 (14)	0.0281 (13)
C24	0.0715 (14)	0.0817 (16)	0.0546 (12)	0.0177 (12)	0.0120 (11)	0.0200 (11)
C25	0.0633 (12)	0.0718 (14)	0.0496 (11)	0.0085 (10)	0.0151 (10)	−0.0023 (9)
C26	0.0647 (12)	0.0514 (10)	0.0512 (10)	0.0083 (9)	0.0243 (9)	0.0015 (8)
C31	0.0993 (19)	0.0769 (16)	0.0746 (16)	0.0360 (14)	0.0434 (15)	0.0067 (12)
C51	0.0601 (10)	0.0442 (9)	0.0375 (8)	−0.0005 (8)	0.0229 (8)	0.0002 (7)
C52	0.0614 (11)	0.0619 (12)	0.0456 (10)	0.0028 (9)	0.0258 (9)	0.0055 (8)
C53	0.0621 (12)	0.0698 (14)	0.0523 (11)	0.0071 (10)	0.0151 (10)	0.0049 (10)
C54	0.0925 (17)	0.0563 (12)	0.0389 (10)	0.0054 (11)	0.0177 (10)	0.0057 (8)
C55	0.1014 (18)	0.0541 (11)	0.0450 (10)	0.0006 (11)	0.0394 (11)	0.0034 (8)
C56	0.0717 (12)	0.0527 (10)	0.0476 (10)	0.0014 (9)	0.0336 (10)	0.0007 (8)
C61	0.0484 (9)	0.0446 (9)	0.0340 (8)	0.0047 (7)	0.0153 (7)	0.0027 (6)
C62	0.0521 (10)	0.0500 (10)	0.0378 (8)	0.0048 (8)	0.0185 (7)	0.0044 (7)
C63	0.0652 (12)	0.0610 (12)	0.0418 (9)	0.0151 (9)	0.0235 (9)	0.0022 (8)
C64	0.0768 (14)	0.0473 (10)	0.0496 (10)	0.0156 (9)	0.0204 (10)	0.0003 (8)
C65	0.0806 (14)	0.0430 (10)	0.0615 (12)	0.0031 (9)	0.0288 (11)	0.0079 (9)
C66	0.0666 (12)	0.0526 (10)	0.0526 (10)	0.0043 (9)	0.0307 (9)	0.0085 (8)
Cl2	0.1170 (7)	0.0679 (8)	0.1060 (7)	−0.0285 (5)	−0.0141 (5)	0.0118 (5)

Cl1—C22	1.748 (3)	C61—C62	1.394 (3)
Cl2—C22	1.70 (2)	C62—C63	1.384 (3)
N1—C6	1.282 (2)	C63—C64	1.378 (3)
N1—C2	1.461 (3)	C64—C65	1.373 (4)
N4—C3	1.462 (3)	C65—C66	1.388 (3)
N4—C5	1.284 (3)	C2—H2	0.9800
C2—C3	1.496 (4)	C3—H3	0.9800
C2—C21	1.512 (3)	C23—H23	0.9300
C3—C31	1.504 (4)	C24—H24	0.9300
C5—C51	1.488 (3)	C25—H25	0.9300
C5—C6	1.491 (3)	C26—H26	0.9300
C6—C61	1.488 (3)	C31—H31A	0.9600
C21—C26	1.387 (3)	C31—H31B	0.9600
C21—C22	1.379 (3)	C31—H31C	0.9600
C22—C23	1.384 (4)	C52—H52	0.9300
C23—C24	1.364 (4)	C53—H53	0.9300
C24—C25	1.370 (4)	C54—H54	0.9300
C25—C26	1.378 (3)	C55—H55	0.9300
C51—C52	1.383 (3)	C56—H56	0.9300
C51—C56	1.392 (3)	C62—H62	0.9300
C52—C53	1.392 (3)	C63—H63	0.9300
C53—C54	1.379 (4)	C64—H64	0.9300
C54—C55	1.369 (5)	C65—H65	0.9300
C55—C56	1.375 (3)	C66—H66	0.9300
C61—C66	1.392 (3)
C2—N1—C6	116.95 (16)	C61—C66—C65	120.5 (2)
C3—N4—C5	117.38 (19)	N1—C2—H2	108.00
N1—C2—C3	110.66 (17)	C3—C2—H2	108.00
N1—C2—C21	109.42 (15)	C21—C2—H2	108.00
C3—C2—C21	113.6 (2)	N4—C3—H3	107.00
N4—C3—C2	111.1 (2)	C2—C3—H3	107.00
N4—C3—C31	109.0 (2)	C31—C3—H3	107.00
C2—C3—C31	115.8 (2)	C22—C23—H23	120.00
N4—C5—C6	119.82 (16)	C24—C23—H23	120.00
N4—C5—C51	117.16 (17)	C23—C24—H24	120.00
C6—C5—C51	122.98 (18)	C25—C24—H24	120.00
N1—C6—C5	121.10 (17)	C24—C25—H25	120.00
N1—C6—C61	116.89 (16)	C26—C25—H25	120.00
C5—C6—C61	121.90 (15)	C21—C26—H26	119.00
C2—C21—C22	124.1 (2)	C25—C26—H26	119.00
C2—C21—C26	119.70 (18)	C3—C31—H31A	109.00
C22—C21—C26	116.25 (19)	C3—C31—H31B	109.00
Cl1—C22—C21	120.9 (2)	C3—C31—H31C	109.00
Cl1—C22—C23	117.1 (2)	H31A—C31—H31B	109.00
C21—C22—C23	122.0 (2)	H31A—C31—H31C	109.00
Cl2—C22—C21	99.7 (10)	H31B—C31—H31C	109.00
Cl2—C22—C23	138.3 (10)	C51—C52—H52	120.00
C22—C23—C24	120.0 (3)	C53—C52—H52	120.00
C23—C24—C25	119.8 (2)	C52—C53—H53	120.00
C24—C25—C26	119.6 (2)	C54—C53—H53	120.00
C21—C26—C25	122.4 (2)	C53—C54—H54	120.00
C5—C51—C52	121.65 (19)	C55—C54—H54	120.00
C5—C51—C56	119.2 (2)	C54—C55—H55	120.00
C52—C51—C56	118.88 (17)	C56—C55—H55	120.00
C51—C52—C53	120.1 (2)	C51—C56—H56	120.00
C52—C53—C54	120.2 (3)	C55—C56—H56	120.00
C53—C54—C55	119.7 (2)	C61—C62—H62	120.00
C54—C55—C56	120.6 (2)	C63—C62—H62	120.00
C51—C56—C55	120.5 (2)	C62—C63—H63	120.00
C6—C61—C62	119.88 (16)	C64—C63—H63	120.00
C6—C61—C66	121.54 (19)	C63—C64—H64	120.00
C62—C61—C66	118.39 (17)	C65—C64—H64	120.00
C61—C62—C63	120.57 (18)	C64—C65—H65	120.00
C62—C63—C64	120.4 (2)	C66—C65—H65	120.00
C63—C64—C65	119.8 (2)	C61—C66—H66	120.00
C64—C65—C66	120.4 (2)	C65—C66—H66	120.00
C6—N1—C2—C3	35.9 (3)	C2—C21—C22—Cl1	−0.7 (4)
C6—N1—C2—C21	161.74 (19)	C2—C21—C22—C23	−179.8 (3)
C2—N1—C6—C5	1.1 (3)	C26—C21—C22—Cl1	179.7 (2)
C2—N1—C6—C61	−175.12 (18)	C26—C21—C22—C23	0.5 (4)
C5—N4—C3—C2	35.6 (3)	C2—C21—C26—C25	179.9 (2)
C5—N4—C3—C31	164.2 (2)	C22—C21—C26—C25	−0.5 (4)
C3—N4—C5—C6	1.5 (3)	Cl1—C22—C23—C24	−179.0 (3)
C3—N4—C5—C51	−176.3 (2)	C21—C22—C23—C24	0.2 (5)
N1—C2—C3—N4	−54.1 (2)	C22—C23—C24—C25	−1.0 (5)
N1—C2—C3—C31	−179.0 (2)	C23—C24—C25—C26	1.1 (5)
C21—C2—C3—N4	−177.59 (17)	C24—C25—C26—C21	−0.3 (4)
C21—C2—C3—C31	57.5 (3)	C5—C51—C52—C53	−173.11 (19)
N1—C2—C21—C22	130.8 (3)	C56—C51—C52—C53	1.4 (3)
N1—C2—C21—C26	−49.6 (3)	C5—C51—C56—C55	174.06 (18)
C3—C2—C21—C22	−105.1 (3)	C52—C51—C56—C55	−0.6 (3)
C3—C2—C21—C26	74.6 (3)	C51—C52—C53—C54	−1.1 (3)
N4—C5—C6—N1	−22.5 (3)	C52—C53—C54—C55	0.0 (3)
N4—C5—C6—C61	153.6 (2)	C53—C54—C55—C56	0.9 (3)
C51—C5—C6—N1	155.2 (2)	C54—C55—C56—C51	−0.6 (3)
C51—C5—C6—C61	−28.8 (3)	C6—C61—C62—C63	175.09 (18)
N4—C5—C51—C52	142.8 (2)	C66—C61—C62—C63	0.0 (3)
N4—C5—C51—C56	−31.7 (3)	C6—C61—C66—C65	−173.53 (19)
C6—C5—C51—C52	−35.0 (3)	C62—C61—C66—C65	1.5 (3)
C6—C5—C51—C56	150.53 (19)	C61—C62—C63—C64	−1.4 (3)
N1—C6—C61—C62	−38.6 (3)	C62—C63—C64—C65	1.4 (3)
N1—C6—C61—C66	136.3 (2)	C63—C64—C65—C66	0.1 (3)
C5—C6—C61—C62	145.14 (19)	C64—C65—C66—C61	−1.6 (3)
C5—C6—C61—C66	−39.9 (3)

Cg2, Cg3 and Cg4 are the centroids of the C21–C26, C51–C56 and C61–C66 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cg4i	0.93	2.80	3.643 (3)	152
C53—H53···Cg2ii	0.93	2.99	3.873 (4)	159
C64—H64···Cg3iii	0.93	2.88	3.729 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C21–C26, C51–C56 and C61–C66 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯Cg4i	0.93	2.80	3.643 (3)	152
C53—H53⋯Cg2ii	0.93	2.99	3.873 (4)	159
C64—H64⋯Cg3iii	0.93	2.88	3.729 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) .