2,2'-{[2-(2-Chloro-phen-yl)-4-methyl-imidazolidine-1,3-di-yl]bis-(methyl-ene)}diphenol.

In the title compound, C24H25ClN2O2, the 2-hy-droxy-benzyl substituents and the 2-chloro-phenyl group occupy the sterically preferred equatorial positions, whereas the methyl group occupies the axial position. The imidazolidine ring adopts an envelope conformation with one of the N atoms adjacent to the methylene group as the flap. The chloro-phenyl substit-uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 73.44 (12)° and the Cl atom is almost coplanar with the C atom bearing the chloro-phenyl substituent [Cl-C-C-C torsion angle = 1.1 (3)°]. The hy-droxy-benzyl groups make dihedral angles of 71.23 (15) and 69.13 (19)° with the mean plane of the heterocyclic ring. The dihedral angle between the two hy-droxy-benzyl groups is 69.61 (12)°. The mol-ecular structure features two intra-molecular O-H⋯N hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.

Related literature

For related structures, see: Rivera et al. (2012a ▶,b ▶). For the synthesis of the title compound, see: Rivera et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H25ClN2O2

M = 408.9

Monoclinic,

a = 7.0281 (2) Å

b = 9.7903 (3) Å

c = 30.3813 (6) Å

β = 94.168 (2)°

V = 2084.92 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 120 K

0.24 × 0.15 × 0.08 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.392, T max = 1

25057 measured reflections

3732 independent reflections

3164 reflections with I > 3σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.081

S = 2.66

3732 reflections

268 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −0.33 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017923/bx2443sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017923/bx2443Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017923/bx2443Isup3.cml

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

C24H25ClN2O2	F(000) = 864
Mr = 408.9	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ycb	Cell parameters from 10626 reflections
a = 7.0281 (2) Å	θ = 2.9–67.0°
b = 9.7903 (3) Å	µ = 0.21 mm−1
c = 30.3813 (6) Å	T = 120 K
β = 94.168 (2)°	Polygon shape, white
V = 2084.92 (10) Å3	0.24 × 0.15 × 0.08 mm
Z = 4

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3732 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3164 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.3784 pixels mm-1	θmax = 25.1°, θmin = 1.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.392, Tmax = 1	l = −36→31
25057 measured reflections

Refinement on F	94 constraints
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.081	Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0004F2)
S = 2.66	(Δ/σ)max = 0.024
3732 reflections	Δρmax = 1.29 e Å−3
268 parameters	Δρmin = −0.33 e Å−3
1 restraint

Experimental. (CrysAlis PRO; Agilent, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Cl1	0.47526 (9)	0.37100 (7)	0.066197 (19)	0.0426 (2)
O1	1.1631 (3)	−0.0315 (2)	0.09734 (7)	0.0521 (7)
N1	0.6652 (3)	0.10467 (19)	0.17016 (6)	0.0276 (5)
N2	0.7887 (3)	0.02087 (19)	0.10763 (6)	0.0281 (5)
O2	0.8058 (3)	0.2490 (2)	0.24193 (6)	0.0533 (7)
C1	0.9092 (3)	−0.1023 (2)	0.04481 (7)	0.0313 (7)
C2	0.7791 (3)	0.2711 (2)	0.11711 (7)	0.0303 (6)
C3	0.9648 (4)	0.2880 (2)	0.13809 (7)	0.0358 (7)
C4	0.8047 (4)	0.5012 (3)	0.08815 (8)	0.0408 (8)
C6	1.0958 (4)	−0.1154 (3)	0.06367 (8)	0.0373 (7)
C5	0.6590 (4)	0.1942 (3)	0.26237 (8)	0.0398 (8)
C7	0.9840 (4)	0.5144 (3)	0.10888 (8)	0.0439 (8)
C8	1.1541 (4)	−0.3039 (3)	0.01561 (7)	0.0405 (8)
C9	0.7795 (3)	0.0089 (2)	0.05926 (7)	0.0327 (7)
C10	0.5015 (4)	0.1449 (3)	0.23719 (8)	0.0374 (7)
C11	1.2177 (4)	−0.2147 (3)	0.04910 (8)	0.0420 (8)
C12	0.7072 (4)	−0.0978 (2)	0.12959 (7)	0.0361 (7)
C13	0.3618 (4)	0.0796 (3)	0.25849 (9)	0.0468 (9)
C14	0.5252 (4)	0.1215 (3)	0.32865 (8)	0.0440 (9)
C15	0.8499 (4)	−0.1925 (3)	0.01111 (7)	0.0375 (7)
C16	0.9707 (4)	−0.2924 (3)	−0.00355 (8)	0.0415 (8)
C17	0.6776 (3)	0.1362 (2)	0.12301 (7)	0.0286 (6)
C18	0.7034 (4)	0.3801 (2)	0.09253 (7)	0.0334 (7)
C19	0.4922 (4)	0.1602 (3)	0.18752 (8)	0.0410 (8)
C20	0.6855 (4)	−0.0468 (2)	0.17574 (8)	0.0383 (8)
C21	0.6697 (4)	0.1850 (3)	0.30818 (8)	0.0436 (8)
C22	0.3725 (5)	0.0669 (3)	0.30433 (9)	0.0513 (10)
C23	1.0644 (4)	0.4083 (3)	0.13432 (8)	0.0407 (8)
C24	0.8613 (5)	−0.0821 (3)	0.20628 (9)	0.0509 (9)
H1c3	1.021974	0.214303	0.155206	0.043*
H1c4	0.749472	0.574892	0.070745	0.049*
H1c7	1.054201	0.597549	0.105794	0.0527*
H1c8	1.237584	−0.373425	0.005822	0.0486*
H1c9	0.815069	0.094296	0.046706	0.0392*
H2c9	0.650655	−0.010354	0.04832	0.0392*
H1c11	1.345868	−0.22167	0.062155	0.0504*
H1c12	0.796755	−0.171914	0.130535	0.0433*
H2c12	0.583691	−0.118423	0.115581	0.0433*
H1c13	0.254234	0.041637	0.241431	0.0562*
H1c14	0.531698	0.11563	0.360265	0.0528*
H1c15	0.722369	−0.185392	−0.002335	0.045*
H1c16	0.926718	−0.353119	−0.026918	0.0499*
H1c17	0.555538	0.146235	0.106973	0.0344*
H1c19	0.382765	0.112164	0.174649	0.0492*
H2c19	0.480064	0.255055	0.179876	0.0492*
H1c20	0.579161	−0.087302	0.188978	0.0459*
H1c21	0.777132	0.222541	0.325396	0.0523*
H1c22	0.27375	0.020425	0.31863	0.0616*
H1c23	1.188841	0.418716	0.1492	0.0489*
H1c24	0.871865	−0.179534	0.209113	0.0611*
H2c24	0.973392	−0.046657	0.194076	0.0611*
H3c24	0.848806	−0.042368	0.234811	0.0611*
H1	1.042 (5)	0.005 (4)	0.1092 (11)	0.0625*
H2	0.785 (5)	0.212 (4)	0.2108 (10)	0.0639*

	U11	U22	U33	U12	U13	U23
Cl1	0.0468 (4)	0.0437 (4)	0.0364 (3)	0.0097 (3)	−0.0034 (2)	0.0023 (2)
O1	0.0435 (11)	0.0589 (13)	0.0526 (11)	−0.0001 (9)	−0.0056 (8)	−0.0247 (9)
N1	0.0304 (9)	0.0255 (10)	0.0272 (9)	−0.0014 (7)	0.0043 (7)	0.0034 (7)
N2	0.0372 (10)	0.0226 (9)	0.0243 (9)	−0.0034 (7)	0.0009 (7)	−0.0007 (7)
O2	0.0551 (12)	0.0583 (13)	0.0464 (11)	−0.0161 (10)	0.0039 (8)	−0.0061 (9)
C1	0.0434 (13)	0.0267 (12)	0.0243 (10)	−0.0071 (9)	0.0052 (8)	0.0018 (8)
C2	0.0372 (12)	0.0283 (12)	0.0259 (10)	−0.0002 (9)	0.0068 (8)	−0.0010 (8)
C3	0.0466 (13)	0.0259 (12)	0.0361 (12)	−0.0080 (10)	0.0104 (10)	−0.0046 (9)
C4	0.0672 (17)	0.0270 (12)	0.0306 (12)	−0.0012 (11)	0.0196 (11)	−0.0022 (9)
C6	0.0465 (14)	0.0359 (13)	0.0295 (11)	−0.0031 (10)	0.0026 (9)	−0.0035 (9)
C5	0.0427 (13)	0.0392 (14)	0.0384 (12)	0.0076 (11)	0.0093 (10)	0.0087 (10)
C7	0.0622 (17)	0.0301 (13)	0.0420 (13)	−0.0130 (12)	0.0209 (11)	−0.0062 (10)
C8	0.0570 (16)	0.0358 (14)	0.0304 (11)	0.0025 (11)	0.0143 (10)	0.0024 (9)
C9	0.0434 (13)	0.0281 (12)	0.0258 (11)	−0.0033 (9)	−0.0021 (9)	0.0003 (8)
C10	0.0397 (13)	0.0395 (14)	0.0337 (12)	0.0115 (10)	0.0073 (9)	0.0046 (9)
C11	0.0479 (15)	0.0433 (15)	0.0349 (12)	0.0027 (12)	0.0047 (10)	0.0007 (10)
C12	0.0491 (14)	0.0249 (12)	0.0344 (12)	−0.0045 (10)	0.0034 (10)	0.0047 (9)
C13	0.0526 (16)	0.0492 (16)	0.0402 (14)	0.0001 (13)	0.0151 (11)	−0.0013 (11)
C14	0.0668 (18)	0.0326 (13)	0.0342 (13)	0.0154 (12)	0.0142 (11)	0.0040 (9)
C15	0.0483 (14)	0.0361 (13)	0.0282 (11)	−0.0084 (11)	0.0036 (9)	−0.0035 (9)
C16	0.0624 (17)	0.0344 (14)	0.0291 (11)	−0.0084 (12)	0.0113 (10)	−0.0072 (9)
C17	0.0296 (11)	0.0293 (12)	0.0266 (10)	−0.0010 (9)	−0.0002 (8)	0.0019 (8)
C18	0.0453 (13)	0.0308 (12)	0.0250 (10)	0.0022 (10)	0.0092 (9)	−0.0022 (8)
C19	0.0355 (12)	0.0549 (16)	0.0329 (12)	0.0113 (11)	0.0047 (9)	0.0066 (10)
C20	0.0508 (14)	0.0277 (12)	0.0370 (12)	−0.0068 (10)	0.0080 (10)	0.0035 (9)
C21	0.0529 (15)	0.0400 (14)	0.0379 (13)	0.0119 (12)	0.0042 (11)	0.0043 (11)
C22	0.0700 (19)	0.0444 (16)	0.0423 (14)	−0.0010 (14)	0.0235 (13)	0.0041 (12)
C23	0.0421 (13)	0.0366 (14)	0.0449 (13)	−0.0096 (11)	0.0121 (10)	−0.0088 (10)
C24	0.0688 (19)	0.0407 (16)	0.0413 (14)	0.0111 (13)	−0.0097 (12)	−0.0010 (11)

O1—C6	1.369 (3)	C9—H1c9	0.96
N1—C17	1.474 (3)	C9—H2c9	0.96
N1—C19	1.465 (3)	C10—C13	1.373 (4)
N1—C20	1.498 (3)	C10—C19	1.513 (3)
N2—C9	1.471 (3)	C11—H1c11	0.96
N2—C12	1.476 (3)	C12—C20	1.507 (3)
N2—C17	1.468 (3)	C12—H1c12	0.96
O2—C5	1.353 (3)	C12—H2c12	0.96
C1—C6	1.398 (3)	C13—C22	1.395 (4)
C1—C9	1.506 (3)	C13—H1c13	0.96
C1—C15	1.392 (3)	C14—C21	1.377 (4)
C2—C3	1.420 (3)	C14—C22	1.367 (4)
C2—C17	1.518 (3)	C14—H1c14	0.96
C2—C18	1.386 (3)	C15—C16	1.389 (4)
C3—C23	1.380 (4)	C15—H1c15	0.96
C3—H1c3	0.96	C16—H1c16	0.96
C4—C7	1.373 (4)	C17—H1c17	0.96
C4—C18	1.394 (4)	C19—H1c19	0.96
C4—H1c4	0.96	C19—H2c19	0.96
C6—C11	1.389 (4)	C20—C24	1.529 (4)
C5—C10	1.386 (3)	C20—H1c20	0.96
C5—C21	1.391 (3)	C21—H1c21	0.96
C7—C23	1.390 (4)	C22—H1c22	0.96
C7—H1c7	0.96	C23—H1c23	0.96
C8—C11	1.390 (4)	C24—H1c24	0.96
C8—C16	1.380 (4)	C24—H2c24	0.96
C8—H1c8	0.96	C24—H3c24	0.96
C17—N1—C19	112.41 (17)	H1c12—C12—H2c12	115.07
C17—N1—C20	107.79 (17)	C10—C13—C22	121.6 (3)
C19—N1—C20	113.64 (19)	C10—C13—H1c13	119.2
C9—N2—C12	113.49 (17)	C22—C13—H1c13	119.2
C9—N2—C17	113.18 (17)	C21—C14—C22	120.5 (2)
C12—N2—C17	103.20 (17)	C21—C14—H1c14	119.73
C6—C1—C9	121.1 (2)	C22—C14—H1c14	119.73
C6—C1—C15	117.7 (2)	C1—C15—C16	121.6 (2)
C9—C1—C15	121.1 (2)	C1—C15—H1c15	119.18
C3—C2—C17	118.20 (19)	C16—C15—H1c15	119.18
C3—C2—C18	117.2 (2)	C8—C16—C15	119.8 (2)
C17—C2—C18	124.6 (2)	C8—C16—H1c16	120.12
C2—C3—C23	121.2 (2)	C15—C16—H1c16	120.12
C2—C3—H1c3	119.42	N1—C17—N2	102.62 (16)
C23—C3—H1c3	119.42	N1—C17—C2	110.98 (17)
C7—C4—C18	119.6 (2)	N1—C17—H1c17	113.65
C7—C4—H1c4	120.18	N2—C17—C2	111.48 (18)
C18—C4—H1c4	120.18	N2—C17—H1c17	113.17
O1—C6—C1	120.9 (2)	C2—C17—H1c17	105.14
O1—C6—C11	118.1 (2)	C2—C18—C4	121.8 (2)
C1—C6—C11	121.0 (2)	N1—C19—C10	110.23 (19)
O2—C5—C10	119.3 (2)	N1—C19—H1c19	109.47
O2—C5—C21	119.8 (2)	N1—C19—H2c19	109.47
C10—C5—C21	120.9 (2)	C10—C19—H1c19	109.47
C4—C7—C23	120.5 (2)	C10—C19—H2c19	109.47
C4—C7—H1c7	119.77	H1c19—C19—H2c19	108.7
C23—C7—H1c7	119.76	N1—C20—C12	103.76 (18)
C11—C8—C16	119.9 (2)	N1—C20—C24	111.0 (2)
C11—C8—H1c8	120.06	N1—C20—H1c20	112.71
C16—C8—H1c8	120.06	C12—C20—C24	111.0 (2)
N2—C9—C1	111.43 (18)	C12—C20—H1c20	112.78
N2—C9—H1c9	109.47	C24—C20—H1c20	105.75
N2—C9—H2c9	109.47	C5—C21—C14	119.5 (2)
C1—C9—H1c9	109.47	C5—C21—H1c21	120.23
C1—C9—H2c9	109.47	C14—C21—H1c21	120.23
H1c9—C9—H2c9	107.44	C13—C22—C14	119.2 (3)
C5—C10—C13	118.1 (2)	C13—C22—H1c22	120.39
C5—C10—C19	119.4 (2)	C14—C22—H1c22	120.39
C13—C10—C19	122.4 (2)	C3—C23—C7	119.7 (2)
C6—C11—C8	120.0 (2)	C3—C23—H1c23	120.14
C6—C11—H1c11	120	C7—C23—H1c23	120.14
C8—C11—H1c11	120	C20—C24—H1c24	109.47
N2—C12—C20	103.23 (18)	C20—C24—H2c24	109.47
N2—C12—H1c12	109.47	C20—C24—H3c24	109.47
N2—C12—H2c12	109.47	H1c24—C24—H2c24	109.47
C20—C12—H1c12	109.47	H1c24—C24—H3c24	109.47
C20—C12—H2c12	109.47	H2c24—C24—H3c24	109.47

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	1.01 (3)	1.79 (3)	2.721 (3)	152 (3)
O2—H2···N1	1.01 (3)	1.79 (3)	2.723 (3)	152 (3)
O1—H1···C9	1.01 (3)	2.31 (3)	2.883 (3)	115 (2)
O2—H2···C19	1.01 (3)	2.19 (4)	2.796 (3)	117 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	1.01 (3)	1.79 (3)	2.721 (3)	152 (3)
O2—H2⋯N1	1.01 (3)	1.79 (3)	2.723 (3)	152 (3)