1,3-Dibenzyl-2-(2-chloro-phen-yl)-4-methyl-imidazolidine.

In the title compound, C24H25ClN2, the methine, methyl-ene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an envelope conformation with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chloro-phenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12)°. The dihedral angles between the chloro-phenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8)°; the dihedral angle between these latter rings is 71.59 (9)°. In the crystal, mol-ecules are linked by C-H⋯Cl inter-actions and a number of weak C-H⋯π inter-actions, involving all three aromatic rings, forming a three-dimensional structure.

Related literature

For uses of imidazolidine-bridged bis­(phenol) derivatives in coordination chemistry, see: Xu et al. (2007 ▶). For related structures, see: Yang et al. (2009 ▶); Xia et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H25ClN2

M = 376.9

Monoclinic,

a = 7.1858 (1) Å

b = 9.8577 (2) Å

c = 29.3310 (5) Å

β = 96.8591 (15)°

V = 2062.80 (6) Å3

Z = 4

Cu Kα radiation

μ = 1.70 mm−1

T = 120 K

0.44 × 0.32 × 0.21 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.62, T max = 0.751

39415 measured reflections

3665 independent reflections

3464 reflections with I > 3σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.144

S = 2.91

3665 reflections

260 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047575/su2527sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047575/su2527Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047575/su2527Isup3.cml

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

C24H25ClN2	Z = 4
Mr = 376.9	F(000) = 800
Monoclinic, P21/c	Dx = 1.213 Mg m−3
Hall symbol: -P 2ycb	Cu Kα radiation, λ = 1.5418 Å
a = 7.1858 (1) Å	Cell parameters from 20478 reflections
b = 9.8577 (2) Å	θ = 3.0–67.0°
c = 29.3310 (5) Å	µ = 1.70 mm−1
β = 96.8591 (15)°	T = 120 K
V = 2062.80 (6) Å3	0.44 × 0.32 × 0.21 mm

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3665 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3464 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.62, Tmax = 0.751	l = −34→34
39415 measured reflections

Refinement on F2	153 constraints
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.144	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 2.91	(Δ/σ)max = 0.047
3665 reflections	Δρmax = 0.24 e Å−3
260 parameters	Δρmin = −0.35 e Å−3
4 restraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl24	−0.02857 (6)	−0.36115 (5)	0.065592 (15)	0.04745 (17)
N8	0.1847 (2)	−0.10600 (13)	0.17251 (5)	0.0361 (4)
N10	0.3151 (2)	−0.02081 (12)	0.11112 (5)	0.0344 (4)
C16	0.7452 (3)	0.2032 (2)	0.05130 (6)	0.0477 (6)
C20	0.5614 (3)	−0.41315 (17)	0.13435 (6)	0.0424 (6)
C2	0.1697 (3)	−0.20165 (19)	0.31553 (7)	0.0497 (6)
C19	0.4692 (2)	−0.29057 (17)	0.13876 (6)	0.0391 (5)
C15	0.6776 (3)	0.30121 (19)	0.01963 (6)	0.0452 (6)
C17	0.6261 (3)	0.10445 (18)	0.06521 (6)	0.0448 (6)
C21	0.4719 (3)	−0.51645 (17)	0.10812 (6)	0.0427 (6)
C1	0.1636 (3)	−0.21435 (18)	0.26802 (6)	0.0432 (6)
C3	0.0314 (3)	−0.13050 (19)	0.33373 (7)	0.0553 (7)
C23	0.2014 (2)	−0.37547 (16)	0.09207 (6)	0.0349 (5)
C22	0.2929 (3)	−0.49840 (16)	0.08697 (6)	0.0399 (5)
C18	0.2879 (2)	−0.26912 (15)	0.11737 (5)	0.0324 (5)
C11	0.3064 (3)	−0.00554 (16)	0.06139 (6)	0.0390 (5)
C6	0.0205 (3)	−0.15668 (17)	0.23914 (6)	0.0406 (6)
C12	0.4379 (3)	0.10288 (16)	0.04778 (5)	0.0362 (5)
C9	0.1973 (2)	−0.13226 (15)	0.12385 (6)	0.0340 (5)
C14	0.4925 (3)	0.29944 (18)	0.00181 (6)	0.0446 (6)
C13	0.3724 (3)	0.20095 (16)	0.01582 (6)	0.0398 (5)
C7	0.0183 (2)	−0.1681 (2)	0.18783 (6)	0.0434 (6)
C25	0.2377 (4)	0.0968 (2)	0.13284 (8)	0.0382 (6)	0.834 (4)
C26'	0.2578 (14)	0.0937 (8)	0.1408 (4)	0.0382 (6)	0.166 (4)
C4	−0.1125 (3)	−0.0734 (2)	0.30561 (8)	0.0593 (8)
C5	−0.1196 (3)	−0.0859 (2)	0.25804 (7)	0.0510 (7)
C27	0.3731 (3)	0.0772 (2)	0.21620 (8)	0.0475 (7)	0.834 (4)
C26	0.2097 (3)	0.04486 (18)	0.18044 (7)	0.0349 (7)	0.834 (4)
C27'	0.4362 (15)	0.1242 (11)	0.1719 (4)	0.047 (4)	0.166 (4)
C25'	0.1081 (17)	0.0315 (6)	0.1670 (4)	0.0349 (7)	0.166 (4)
H1c16	0.875012	0.203631	0.063679	0.0573*
H1c20	0.686283	−0.426164	0.149381	0.0509*
H1c2	0.269944	−0.242418	0.335449	0.0596*
H1c19	0.531872	−0.21934	0.156898	0.047*
H1c15	0.760026	0.369776	0.01026	0.0543*
H1c17	0.674392	0.036817	0.087035	0.0538*
H1c21	0.535525	−0.600857	0.104771	0.0513*
H1c1	0.260406	−0.263872	0.255352	0.0518*
H1c3	0.036117	−0.120936	0.366424	0.0664*
H1c22	0.231051	−0.569829	0.068775	0.0479*
H1c11	0.180416	0.015881	0.048777	0.0468*
H2c11	0.336042	−0.090551	0.04801	0.0468*
H1c9	0.077614	−0.135976	0.105426	0.0408*
H1c14	0.445321	0.366312	−0.020417	0.0535*
H1c13	0.242801	0.200852	0.003238	0.0478*
H1c7	0.01236	−0.26198	0.179091	0.0521*
H2c7	−0.092009	−0.124555	0.172859	0.0521*
H1c4	−0.209051	−0.024474	0.318574	0.0711*
H1c5	−0.221036	−0.045807	0.238336	0.0612*
H1c25	0.328399	0.168788	0.135627	0.0458*	0.834 (4)
H2c25	0.118473	0.120137	0.116385	0.0458*	0.834 (4)
H1c27	0.487331	0.046259	0.205703	0.057*	0.834 (4)
H2c27	0.379789	0.173462	0.221124	0.057*	0.834 (4)
H3c27	0.356064	0.032474	0.244474	0.057*	0.834 (4)
H1c26	0.105513	0.086723	0.192608	0.0419*	0.834 (4)
H1c26'	0.209453	0.174743	0.125584	0.0458*	0.166 (4)
H1c25'	0.111895	0.073924	0.196512	0.0419*	0.166 (4)
H2c25'	−0.009138	0.028882	0.147483	0.0419*	0.166 (4)
H1c27'	0.497636	0.040672	0.181514	0.0568*	0.166 (4)
H2c27'	0.517824	0.178023	0.155616	0.0568*	0.166 (4)
H3c27'	0.406452	0.173148	0.198402	0.0568*	0.166 (4)

	U11	U22	U33	U12	U13	U23
Cl24	0.0489 (3)	0.0456 (3)	0.0467 (3)	0.00039 (17)	0.0010 (2)	−0.00135 (17)
N8	0.0483 (8)	0.0258 (7)	0.0366 (7)	0.0073 (5)	0.0153 (6)	0.0017 (5)
N10	0.0490 (8)	0.0239 (6)	0.0314 (7)	0.0070 (5)	0.0101 (6)	0.0025 (5)
C16	0.0496 (10)	0.0535 (11)	0.0411 (10)	0.0026 (8)	0.0098 (8)	−0.0068 (8)
C20	0.0465 (10)	0.0350 (9)	0.0471 (10)	0.0140 (7)	0.0113 (8)	0.0070 (7)
C2	0.0659 (12)	0.0420 (10)	0.0414 (10)	−0.0193 (9)	0.0072 (9)	0.0011 (8)
C19	0.0453 (9)	0.0294 (8)	0.0434 (9)	0.0075 (7)	0.0082 (8)	0.0015 (7)
C15	0.0613 (11)	0.0405 (9)	0.0372 (9)	−0.0035 (8)	0.0201 (8)	−0.0063 (7)
C17	0.0572 (11)	0.0400 (9)	0.0379 (9)	0.0119 (8)	0.0081 (8)	0.0038 (7)
C21	0.0600 (11)	0.0303 (8)	0.0416 (9)	0.0145 (7)	0.0213 (9)	0.0054 (7)
C1	0.0512 (10)	0.0357 (9)	0.0437 (10)	−0.0076 (7)	0.0101 (8)	−0.0007 (7)
C3	0.0879 (16)	0.0390 (10)	0.0423 (11)	−0.0265 (10)	0.0210 (11)	−0.0051 (8)
C23	0.0434 (9)	0.0314 (8)	0.0315 (8)	0.0037 (6)	0.0114 (7)	0.0047 (6)
C22	0.0612 (11)	0.0268 (8)	0.0346 (9)	0.0023 (7)	0.0178 (8)	0.0006 (6)
C18	0.0436 (9)	0.0244 (7)	0.0310 (7)	0.0061 (6)	0.0119 (7)	0.0032 (6)
C11	0.0563 (10)	0.0289 (8)	0.0328 (8)	0.0049 (7)	0.0090 (8)	0.0008 (6)
C6	0.0492 (10)	0.0338 (9)	0.0416 (10)	−0.0023 (7)	0.0175 (8)	0.0007 (7)
C12	0.0541 (10)	0.0270 (8)	0.0290 (8)	0.0070 (7)	0.0111 (7)	−0.0011 (6)
C9	0.0408 (9)	0.0265 (8)	0.0351 (9)	0.0083 (6)	0.0069 (7)	0.0022 (6)
C14	0.0663 (12)	0.0326 (9)	0.0368 (9)	0.0053 (8)	0.0142 (8)	0.0040 (7)
C13	0.0532 (10)	0.0331 (8)	0.0342 (8)	0.0067 (7)	0.0093 (8)	0.0025 (7)
C7	0.0403 (9)	0.0503 (10)	0.0409 (10)	0.0051 (7)	0.0099 (8)	0.0029 (8)
C25	0.0524 (11)	0.0271 (8)	0.0357 (11)	0.0063 (7)	0.0082 (9)	−0.0031 (8)
C26'	0.0524 (11)	0.0271 (8)	0.0357 (11)	0.0063 (7)	0.0082 (9)	−0.0031 (8)
C4	0.0835 (15)	0.0404 (10)	0.0624 (13)	−0.0097 (10)	0.0439 (12)	−0.0095 (9)
C5	0.0574 (12)	0.0454 (10)	0.0544 (11)	0.0045 (8)	0.0241 (10)	0.0034 (9)
C27	0.0632 (14)	0.0351 (11)	0.0427 (12)	−0.0055 (10)	0.0004 (10)	0.0021 (9)
C26	0.0446 (14)	0.0231 (8)	0.0384 (11)	0.0061 (8)	0.0109 (10)	−0.0018 (7)
C27'	0.044 (6)	0.042 (6)	0.056 (7)	−0.006 (4)	0.007 (5)	−0.018 (5)
C25'	0.0446 (14)	0.0231 (8)	0.0384 (11)	0.0061 (8)	0.0109 (10)	−0.0018 (7)

N8—C9	1.464 (2)	C18—C9	1.520 (2)
N8—C7	1.461 (2)	C11—C12	1.511 (2)
N8—C26	1.513 (2)	C11—H1c11	0.96
N8—C25'	1.464 (7)	C11—H2c11	0.96
N10—C11	1.460 (2)	C6—C7	1.507 (3)
N10—C9	1.462 (2)	C6—C5	1.393 (3)
N10—C25	1.464 (3)	C12—C13	1.389 (2)
N10—C26'	1.512 (10)	C9—H1c9	0.96
C16—C15	1.387 (3)	C14—C13	1.393 (3)
C16—C17	1.389 (3)	C14—H1c14	0.96
C16—H1c16	0.96	C13—H1c13	0.96
C20—C19	1.391 (2)	C7—H1c7	0.96
C20—C21	1.387 (2)	C7—H2c7	0.96
C20—H1c20	0.96	C25—C26	1.523 (3)
C2—C1	1.395 (3)	C25—H1c25	0.96
C2—C3	1.375 (3)	C25—H2c25	0.96
C2—H1c2	0.96	C26'—C27'	1.512 (14)
C19—C18	1.393 (2)	C26'—C25'	1.523 (16)
C19—H1c19	0.96	C26'—H1c26'	0.96
C15—C14	1.370 (3)	C4—C5	1.395 (3)
C15—H1c15	0.96	C4—H1c4	0.96
C17—C12	1.388 (3)	C5—H1c5	0.96
C17—H1c17	0.96	C27—C26	1.512 (3)
C21—C22	1.371 (3)	C27—H1c27	0.96
C21—H1c21	0.96	C27—H2c27	0.96
C1—C6	1.375 (2)	C27—H3c27	0.96
C1—H1c1	0.96	C26—H1c26	0.96
C3—C4	1.365 (3)	C27'—H1c27'	0.96
C3—H1c3	0.96	C27'—H2c27'	0.96
C23—C22	1.395 (2)	C27'—H3c27'	0.96
C23—C18	1.388 (2)	C25'—H1c25'	0.96
C22—H1c22	0.96	C25'—H2c25'	0.96
C9—N8—C7	111.94 (13)	N8—C9—H1c9	113.6
C9—N8—C26	107.69 (13)	N10—C9—C18	111.41 (14)
C9—N8—C25'	97.0 (5)	N10—C9—H1c9	113.07
C7—N8—C26	116.80 (15)	C18—C9—H1c9	105.31
C7—N8—C25'	96.4 (5)	C15—C14—C13	120.25 (16)
C11—N10—C9	112.07 (12)	C15—C14—H1c14	119.88
C11—N10—C25	112.33 (14)	C13—C14—H1c14	119.88
C11—N10—C26'	121.1 (4)	C12—C13—C14	120.82 (17)
C9—N10—C25	102.85 (15)	C12—C13—H1c13	119.59
C9—N10—C26'	102.0 (4)	C14—C13—H1c13	119.59
C15—C16—C17	120.43 (18)	N8—C7—C6	111.35 (14)
C15—C16—H1c16	119.79	N8—C7—H1c7	109.47
C17—C16—H1c16	119.78	N8—C7—H2c7	109.47
C19—C20—C21	119.66 (16)	C6—C7—H1c7	109.47
C19—C20—H1c20	120.17	C6—C7—H2c7	109.47
C21—C20—H1c20	120.17	H1c7—C7—H2c7	107.53
C1—C2—C3	119.75 (18)	N10—C25—C26	103.37 (16)
C1—C2—H1c2	120.13	N10—C25—H1c25	109.47
C3—C2—H1c2	120.13	N10—C25—H2c25	109.47
C20—C19—C18	121.33 (15)	C26—C25—H1c25	109.47
C20—C19—H1c19	119.33	C26—C25—H2c25	109.47
C18—C19—H1c19	119.33	H1c25—C25—H2c25	114.95
C16—C15—C14	119.51 (18)	N10—C26'—C27'	103.1 (7)
C16—C15—H1c15	120.24	N10—C26'—C25'	104.3 (6)
C14—C15—H1c15	120.25	N10—C26'—H1c26'	117.48
C16—C17—C12	120.46 (16)	C27'—C26'—C25'	112.0 (9)
C16—C17—H1c17	119.77	C27'—C26'—H1c26'	110.43
C12—C17—H1c17	119.77	C25'—C26'—H1c26'	109.35
C20—C21—C22	120.22 (16)	C3—C4—C5	120.1 (2)
C20—C21—H1c21	119.89	C3—C4—H1c4	119.92
C22—C21—H1c21	119.89	C5—C4—H1c4	119.93
C2—C1—C6	120.67 (18)	C6—C5—C4	120.03 (19)
C2—C1—H1c1	119.66	C6—C5—H1c5	119.98
C6—C1—H1c1	119.66	C4—C5—H1c5	119.98
C2—C3—C4	120.4 (2)	C26—C27—H1c27	109.47
C2—C3—H1c3	119.8	C26—C27—H2c27	109.47
C4—C3—H1c3	119.8	C26—C27—H3c27	109.47
C22—C23—C18	121.77 (15)	H1c27—C27—H2c27	109.47
C21—C22—C23	119.53 (15)	H1c27—C27—H3c27	109.47
C21—C22—H1c22	120.23	H2c27—C27—H3c27	109.47
C23—C22—H1c22	120.24	N8—C26—C25	102.47 (15)
C19—C18—C23	117.47 (14)	N8—C26—C27	112.46 (16)
C19—C18—C9	118.05 (13)	N8—C26—H1c26	113.36
C23—C18—C9	124.48 (14)	C25—C26—C27	112.82 (19)
N10—C11—C12	112.54 (13)	C25—C26—H1c26	113
N10—C11—H1c11	109.47	C27—C26—H1c26	103.12
N10—C11—H2c11	109.47	C26'—C27'—H1c27'	109.47
C12—C11—H1c11	109.47	C26'—C27'—H2c27'	109.47
C12—C11—H2c11	109.47	C26'—C27'—H3c27'	109.47
H1c11—C11—H2c11	106.21	H1c27'—C27'—H2c27'	109.47
C1—C6—C7	120.16 (17)	H1c27'—C27'—H3c27'	109.47
C1—C6—C5	119.00 (18)	H2c27'—C27'—H3c27'	109.47
C7—C6—C5	120.83 (16)	N8—C25'—C26'	98.6 (8)
C17—C12—C11	121.54 (15)	N8—C25'—H1c25'	109.47
C17—C12—C13	118.53 (16)	N8—C25'—H2c25'	109.47
C11—C12—C13	119.89 (15)	C26'—C25'—H1c25'	109.47
N8—C9—N10	102.77 (12)	C26'—C25'—H2c25'	109.47
N8—C9—C18	110.86 (12)	H1c25'—C25'—H2c25'	118.51

D—H···A	D—H	H···A	D···A	D—H···A
C9—H1C9···Cl24	0.96	2.58	3.1596 (16)	119
C21—H1c21···Cg2i	0.96	2.87	3.6324 (19)	137
C11—H2c11···Cg2ii	0.96	2.82	3.6192 (19)	142
C4—H1c4···Cg3iii	0.96	2.79	3.695 (2)	157
C26—H1c26···Cg1iii	0.96	2.91	3.688 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C12–C17 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H1C9⋯Cl24	0.96	2.58	3.1596 (16)	119
C21—H1c21⋯Cg2i	0.96	2.87	3.6324 (19)	137
C11—H2c11⋯Cg2ii	0.96	2.82	3.6192 (19)	142
C4—H1c4⋯Cg3iii	0.96	2.79	3.695 (2)	157
C26—H1c26⋯Cg1iii	0.96	2.91	3.688 (2)	139

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