1,3-Bis(4-tert-butyl-benz-yl)-4,5-dihydro-imidazolium chloride monohydrate.

In the title compound, C(25)H(35)N(2) (+)·Cl(-)·H(2)O, the imidazolidine ring adopts a twisted conformation, with a pseudo-twofold axis passing through the N-C-N carbon and the opposite C-C bond. The N-C-N fragment of the imidazolidine ring shows some degree of both double- and single-bond character due to partial electron delocalization. One of the tert-butyl groups is disordered over two conformations with occupancies of 0.714 (8) and 0.286 (8). In the crystal, O-H⋯Cl and C-H⋯O hydrogen bonds help to establish the packing.

Related literature

For synthesis, see: Yaşar et al. (2008 ▶); Özdemir et al. (2004a ▶, 2004b ▶). For general background, see: Herrmann et al. (1998 ▶); Glorius (2007 ▶); Nolan (2006 ▶). For related compounds, see: Arslan et al. (2009a ▶,b ▶) and references therein. For bond-length data, see: Allen et al. (1987 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C25H35N2 +·Cl−·H2O

M = 417.02

Monoclinic,

a = 18.205 (4) Å

b = 10.148 (2) Å

c = 13.452 (3) Å

β = 100.01 (3)°

V = 2447.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 153 (2) K

0.43 × 0.17 × 0.05 mm

Data collection

Rigaku AFC 8S Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.929, T max = 0.991

17800 measured reflections

4297 independent reflections

2886 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.207

S = 1.03

4297 reflections

299 parameters

50 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000452/hg2460sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000452/hg2460Isup2.hkl

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

C25H35N2+·Cl−·H2O	F(000) = 904
Mr = 417.02	Dx = 1.132 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5990 reflections
a = 18.205 (4) Å	θ = 2.3–26.7°
b = 10.148 (2) Å	µ = 0.17 mm−1
c = 13.452 (3) Å	T = 153 K
β = 100.01 (3)°	Plate, colorless
V = 2447.3 (9) Å3	0.43 × 0.17 × 0.05 mm
Z = 4

Rigaku AFC 8S Mercury CCD diffractometer	4297 independent reflections
Radiation source: Sealed Tube	2886 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.072
Detector resolution: 14.6306 pixels mm-1	θmax = 25.0°, θmin = 2.3°
ω scans	h = −15→21
Absorption correction: multi-scan (Jacobson, 1998)	k = −12→12
Tmin = 0.929, Tmax = 0.991	l = −16→16
17800 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0868P)2 + 3.6749P] where P = (Fo2 + 2Fc2)/3
4297 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.28 e Å−3
50 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.55770 (5)	0.59372 (8)	0.69855 (6)	0.0407 (2)
C1	0.44642 (19)	0.3585 (3)	0.5584 (2)	0.0329 (7)
H1	0.4673	0.4424	0.5810	0.040*
C2	0.3626 (2)	0.2034 (3)	0.4864 (3)	0.0408 (8)
H2A	0.3513	0.1950	0.4143	0.049*
H2B	0.3225	0.1667	0.5152	0.049*
C3	0.43716 (19)	0.1369 (3)	0.5294 (2)	0.0348 (7)
H3A	0.4319	0.0779	0.5835	0.042*
H3B	0.4564	0.0890	0.4781	0.042*
C4	0.56104 (19)	0.2349 (3)	0.6223 (2)	0.0358 (8)
H4A	0.5607	0.1721	0.6756	0.043*
H4B	0.5765	0.3181	0.6530	0.043*
C5	0.61762 (19)	0.1916 (3)	0.5590 (2)	0.0328 (7)
C6	0.61032 (19)	0.2201 (3)	0.4561 (2)	0.0362 (8)
H6	0.5660	0.2627	0.4218	0.043*
C7	0.6664 (2)	0.1874 (4)	0.4035 (3)	0.0402 (8)
H7	0.6597	0.2071	0.3327	0.048*
C8	0.73238 (19)	0.1271 (3)	0.4493 (3)	0.0360 (8)
C9	0.7385 (2)	0.0989 (4)	0.5517 (3)	0.0422 (8)
H9	0.7831	0.0576	0.5863	0.051*
C10	0.6820 (2)	0.1288 (4)	0.6052 (3)	0.0433 (9)
H10	0.6877	0.1055	0.6753	0.052*
C11	0.7948 (2)	0.0960 (4)	0.3890 (3)	0.0421 (8)
C12	0.7640 (4)	0.0329 (9)	0.2899 (5)	0.073 (2)	0.714 (8)
H12A	0.7393	−0.0478	0.3016	0.109*	0.714 (8)
H12B	0.8039	0.0146	0.2538	0.109*	0.714 (8)
H12C	0.7289	0.0916	0.2508	0.109*	0.714 (8)
C12'	0.7917 (13)	−0.0488 (16)	0.367 (2)	0.109 (9)	0.286 (8)
H12D	0.7449	−0.0699	0.3251	0.164*	0.286 (8)
H12E	0.7963	−0.0969	0.4293	0.164*	0.286 (8)
H12F	0.8319	−0.0724	0.3328	0.164*	0.286 (8)
C13	0.8549 (4)	0.0036 (8)	0.4466 (5)	0.072 (2)	0.714 (8)
H13A	0.8746	0.0411	0.5112	0.108*	0.714 (8)
H13B	0.8944	−0.0073	0.4084	0.108*	0.714 (8)
H13C	0.8331	−0.0807	0.4559	0.108*	0.714 (8)
C13'	0.8687 (10)	0.148 (3)	0.4447 (14)	0.109 (10)	0.286 (8)
H13D	0.8605	0.1968	0.5031	0.164*	0.286 (8)
H13E	0.8905	0.2053	0.4008	0.164*	0.286 (8)
H13F	0.9017	0.0759	0.4654	0.164*	0.286 (8)
C14	0.8337 (4)	0.2256 (7)	0.3712 (7)	0.072 (2)	0.714 (8)
H14A	0.8539	0.2650	0.4350	0.108*	0.714 (8)
H14B	0.7982	0.2847	0.3332	0.108*	0.714 (8)
H14C	0.8732	0.2084	0.3341	0.108*	0.714 (8)
C14'	0.7827 (11)	0.1702 (19)	0.2853 (13)	0.080 (6)	0.286 (8)
H14D	0.7322	0.1582	0.2516	0.121*	0.286 (8)
H14E	0.8162	0.1355	0.2440	0.121*	0.286 (8)
H14F	0.7923	0.2625	0.2967	0.121*	0.286 (8)
C15	0.3209 (2)	0.4448 (4)	0.4915 (3)	0.0431 (9)
H15A	0.3039	0.4452	0.4198	0.052*
H15B	0.3433	0.5288	0.5102	0.052*
C16	0.2551 (2)	0.4253 (3)	0.5442 (3)	0.0377 (8)
C17	0.2655 (2)	0.4019 (5)	0.6469 (3)	0.0528 (10)
H17	0.3153	0.3980	0.6849	0.063*
C18	0.2052 (2)	0.3841 (5)	0.6957 (3)	0.0532 (11)
H18	0.2142	0.3690	0.7673	0.064*
C19	0.1325 (2)	0.3875 (3)	0.6443 (3)	0.0382 (8)
C20	0.1231 (2)	0.4119 (5)	0.5426 (3)	0.0550 (11)
H20	0.0734	0.4161	0.5043	0.066*
C21	0.1835 (2)	0.4307 (5)	0.4932 (3)	0.0549 (11)
H21	0.1746	0.4478	0.4219	0.066*
C22	0.0654 (2)	0.3722 (4)	0.6988 (3)	0.0459 (9)
C23	0.0852 (3)	0.2921 (5)	0.7956 (3)	0.0615 (11)
H23A	0.1047	0.2080	0.7805	0.092*
H23B	0.0414	0.2794	0.8251	0.092*
H23C	0.1221	0.3386	0.8424	0.092*
C24	0.0407 (3)	0.5107 (5)	0.7246 (4)	0.0754 (15)
H24A	−0.0034	0.5045	0.7543	0.113*
H24B	0.0303	0.5626	0.6641	0.113*
H24C	0.0798	0.5517	0.7714	0.113*
C25	0.0003 (2)	0.3024 (5)	0.6312 (4)	0.0649 (12)
H25A	0.0168	0.2187	0.6103	0.097*
H25B	−0.0170	0.3557	0.5729	0.097*
H25C	−0.0397	0.2892	0.6684	0.097*
N1	0.48540 (15)	0.2483 (3)	0.5661 (2)	0.0333 (6)
N2	0.37630 (16)	0.3421 (3)	0.5169 (2)	0.0353 (6)
O1	0.55870 (15)	0.5901 (2)	0.2126 (2)	0.0442 (6)
H1A	0.525 (2)	0.546 (4)	0.235 (3)	0.066*
H1B	0.556 (3)	0.6725 (19)	0.209 (3)	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0513 (5)	0.0360 (4)	0.0371 (4)	−0.0030 (4)	0.0140 (4)	−0.0004 (3)
C1	0.0419 (18)	0.0288 (16)	0.0323 (16)	−0.0043 (14)	0.0180 (14)	−0.0020 (13)
C2	0.0445 (19)	0.0341 (18)	0.047 (2)	−0.0023 (15)	0.0157 (16)	−0.0088 (15)
C3	0.0415 (19)	0.0288 (16)	0.0351 (17)	−0.0036 (14)	0.0090 (15)	−0.0034 (13)
C4	0.0428 (18)	0.0371 (18)	0.0269 (16)	−0.0023 (14)	0.0043 (14)	−0.0020 (13)
C5	0.0401 (18)	0.0248 (15)	0.0344 (17)	−0.0064 (13)	0.0090 (14)	−0.0005 (12)
C6	0.0362 (17)	0.0407 (18)	0.0309 (17)	0.0022 (14)	0.0040 (14)	0.0005 (14)
C7	0.046 (2)	0.046 (2)	0.0277 (17)	−0.0003 (16)	0.0047 (15)	−0.0005 (14)
C8	0.0364 (18)	0.0312 (17)	0.0402 (18)	−0.0057 (14)	0.0059 (15)	−0.0048 (13)
C9	0.043 (2)	0.047 (2)	0.0370 (19)	0.0046 (16)	0.0062 (15)	0.0041 (15)
C10	0.048 (2)	0.055 (2)	0.0267 (17)	0.0061 (17)	0.0065 (15)	0.0049 (15)
C11	0.0412 (19)	0.046 (2)	0.042 (2)	0.0009 (16)	0.0138 (16)	−0.0027 (16)
C12	0.063 (4)	0.099 (6)	0.059 (4)	0.001 (4)	0.019 (3)	−0.028 (4)
C12'	0.127 (18)	0.048 (10)	0.19 (2)	−0.011 (11)	0.117 (18)	−0.025 (12)
C13	0.059 (4)	0.091 (5)	0.073 (5)	0.039 (4)	0.030 (3)	0.012 (4)
C13'	0.047 (10)	0.22 (3)	0.065 (12)	−0.012 (14)	0.020 (9)	−0.004 (16)
C14	0.059 (4)	0.063 (4)	0.105 (6)	−0.009 (3)	0.045 (4)	0.004 (4)
C14'	0.099 (14)	0.085 (13)	0.071 (11)	0.030 (11)	0.054 (10)	0.024 (9)
C15	0.042 (2)	0.0412 (19)	0.047 (2)	0.0041 (15)	0.0108 (17)	0.0045 (16)
C16	0.0409 (19)	0.0320 (17)	0.0409 (19)	0.0025 (14)	0.0090 (15)	−0.0021 (14)
C17	0.0345 (19)	0.084 (3)	0.040 (2)	0.0040 (19)	0.0053 (16)	−0.0035 (19)
C18	0.040 (2)	0.084 (3)	0.0345 (19)	0.005 (2)	0.0060 (16)	−0.0025 (19)
C19	0.0384 (19)	0.0323 (17)	0.0443 (19)	0.0036 (14)	0.0082 (15)	−0.0051 (14)
C20	0.038 (2)	0.076 (3)	0.048 (2)	0.004 (2)	0.0007 (17)	0.011 (2)
C21	0.050 (2)	0.074 (3)	0.040 (2)	0.004 (2)	0.0046 (18)	0.0118 (19)
C22	0.041 (2)	0.041 (2)	0.058 (2)	0.0041 (16)	0.0158 (18)	0.0008 (17)
C23	0.062 (3)	0.066 (3)	0.062 (3)	−0.009 (2)	0.023 (2)	0.007 (2)
C24	0.080 (3)	0.052 (3)	0.109 (4)	0.010 (2)	0.058 (3)	−0.001 (3)
C25	0.045 (2)	0.069 (3)	0.079 (3)	−0.010 (2)	0.007 (2)	0.012 (2)
N1	0.0390 (15)	0.0285 (13)	0.0340 (14)	−0.0035 (11)	0.0107 (12)	−0.0051 (11)
N2	0.0404 (16)	0.0305 (14)	0.0373 (15)	−0.0010 (12)	0.0130 (12)	−0.0010 (11)
O1	0.0508 (15)	0.0368 (13)	0.0481 (15)	−0.0018 (12)	0.0171 (12)	0.0024 (11)

C1—N2	1.312 (4)	C13—H13C	0.9600
C1—N1	1.319 (4)	C13'—H13D	0.9600
C1—H1	0.9600	C13'—H13E	0.9600
C2—N2	1.475 (4)	C13'—H13F	0.9600
C2—C3	1.536 (5)	C14—H14A	0.9600
C2—H2A	0.9600	C14—H14B	0.9600
C2—H2B	0.9600	C14—H14C	0.9600
C3—N1	1.463 (4)	C14'—H14D	0.9600
C3—H3A	0.9600	C14'—H14E	0.9600
C3—H3B	0.9600	C14'—H14F	0.9600
C4—N1	1.458 (4)	C15—N2	1.449 (4)
C4—C5	1.511 (5)	C15—C16	1.506 (5)
C4—H4A	0.9600	C15—H15A	0.9600
C4—H4B	0.9600	C15—H15B	0.9600
C5—C10	1.383 (5)	C16—C21	1.365 (5)
C5—C6	1.398 (5)	C16—C17	1.381 (5)
C6—C7	1.380 (5)	C17—C18	1.386 (6)
C6—H6	0.9600	C17—H17	0.9600
C7—C8	1.392 (5)	C18—C19	1.383 (5)
C7—H7	0.9600	C18—H18	0.9600
C8—C9	1.392 (5)	C19—C20	1.372 (5)
C8—C11	1.539 (5)	C19—C22	1.538 (5)
C9—C10	1.387 (5)	C20—C21	1.393 (6)
C9—H9	0.9600	C20—H20	0.9600
C10—H10	0.9600	C21—H21	0.9600
C11—C12	1.497 (7)	C22—C23	1.525 (6)
C11—C12'	1.498 (16)	C22—C24	1.534 (6)
C11—C13'	1.517 (18)	C22—C25	1.535 (6)
C11—C14	1.532 (7)	C23—H23A	0.9599
C11—C13	1.544 (7)	C23—H23B	0.9599
C11—C14'	1.567 (15)	C23—H23C	0.9599
C12—H12A	0.9600	C24—H24A	0.9599
C12—H12B	0.9600	C24—H24B	0.9599
C12—H12C	0.9600	C24—H24C	0.9599
C12'—H12D	0.9600	C25—H25A	0.9599
C12'—H12E	0.9600	C25—H25B	0.9599
C12'—H12F	0.9600	C25—H25C	0.9599
C13—H13A	0.9600	O1—H1A	0.85 (3)
C13—H13B	0.9600	O1—H1B	0.839 (18)
N2—C1—N1	113.4 (3)	H13D—C13'—H13E	109.5
N2—C1—H1	123.3	C11—C13'—H13F	109.5
N1—C1—H1	123.3	H13D—C13'—H13F	109.5
N2—C2—C3	102.7 (3)	H13E—C13'—H13F	109.5
N2—C2—H2A	111.2	C11—C14—H14A	109.5
C3—C2—H2A	111.2	C11—C14—H14B	109.5
N2—C2—H2B	111.2	H14A—C14—H14B	109.5
C3—C2—H2B	111.2	C11—C14—H14C	109.5
H2A—C2—H2B	109.1	H14A—C14—H14C	109.5
N1—C3—C2	103.1 (3)	H14B—C14—H14C	109.5
N1—C3—H3A	111.1	C11—C14'—H14D	109.5
C2—C3—H3A	111.1	C11—C14'—H14E	109.5
N1—C3—H3B	111.1	H14D—C14'—H14E	109.5
C2—C3—H3B	111.1	C11—C14'—H14F	109.5
H3A—C3—H3B	109.1	H14D—C14'—H14F	109.5
N1—C4—C5	114.2 (3)	H14E—C14'—H14F	109.5
N1—C4—H4A	108.7	N2—C15—C16	111.9 (3)
C5—C4—H4A	108.7	N2—C15—H15A	109.2
N1—C4—H4B	108.7	C16—C15—H15A	109.2
C5—C4—H4B	108.7	N2—C15—H15B	109.2
H4A—C4—H4B	107.6	C16—C15—H15B	109.2
C10—C5—C6	117.9 (3)	H15A—C15—H15B	107.9
C10—C5—C4	119.2 (3)	C21—C16—C17	117.6 (4)
C6—C5—C4	122.8 (3)	C21—C16—C15	121.7 (3)
C7—C6—C5	120.4 (3)	C17—C16—C15	120.7 (3)
C7—C6—H6	119.8	C16—C17—C18	120.9 (4)
C5—C6—H6	119.8	C16—C17—H17	119.5
C6—C7—C8	122.5 (3)	C18—C17—H17	119.5
C6—C7—H7	118.8	C19—C18—C17	121.9 (4)
C8—C7—H7	118.8	C19—C18—H18	119.1
C9—C8—C7	116.2 (3)	C17—C18—H18	119.1
C9—C8—C11	122.7 (3)	C20—C19—C18	116.5 (4)
C7—C8—C11	121.1 (3)	C20—C19—C22	121.4 (3)
C10—C9—C8	122.0 (3)	C18—C19—C22	122.0 (3)
C10—C9—H9	119.0	C19—C20—C21	121.9 (4)
C8—C9—H9	119.0	C19—C20—H20	119.1
C5—C10—C9	121.0 (3)	C21—C20—H20	119.1
C5—C10—H10	119.5	C16—C21—C20	121.3 (4)
C9—C10—H10	119.5	C16—C21—H21	119.4
C12'—C11—C13'	116.1 (15)	C20—C21—H21	119.4
C12—C11—C14	109.9 (5)	C23—C22—C24	109.3 (4)
C12—C11—C8	111.1 (4)	C23—C22—C25	107.7 (3)
C12'—C11—C8	107.4 (8)	C24—C22—C25	109.3 (4)
C13'—C11—C8	109.9 (8)	C23—C22—C19	111.8 (3)
C14—C11—C8	108.1 (4)	C24—C22—C19	107.7 (3)
C12—C11—C13	108.1 (5)	C25—C22—C19	111.1 (3)
C14—C11—C13	107.1 (5)	C22—C23—H23A	109.5
C8—C11—C13	112.6 (4)	C22—C23—H23B	109.5
C12'—C11—C14'	107.6 (13)	H23A—C23—H23B	109.5
C13'—C11—C14'	104.3 (12)	C22—C23—H23C	109.5
C8—C11—C14'	111.6 (7)	H23A—C23—H23C	109.5
C11—C12—H12A	109.5	H23B—C23—H23C	109.5
C11—C12—H12B	109.5	C22—C24—H24A	109.5
H12A—C12—H12B	109.5	C22—C24—H24B	109.5
C11—C12—H12C	109.5	H24A—C24—H24B	109.5
H12A—C12—H12C	109.5	C22—C24—H24C	109.5
H12B—C12—H12C	109.5	H24A—C24—H24C	109.5
C11—C12'—H12D	109.5	H24B—C24—H24C	109.5
C11—C12'—H12E	109.5	C22—C25—H25A	109.5
H12D—C12'—H12E	109.5	C22—C25—H25B	109.5
C11—C12'—H12F	109.5	H25A—C25—H25B	109.5
H12D—C12'—H12F	109.5	C22—C25—H25C	109.5
H12E—C12'—H12F	109.5	H25A—C25—H25C	109.5
C11—C13—H13A	109.5	H25B—C25—H25C	109.5
C11—C13—H13B	109.5	C1—N1—C4	124.5 (3)
H13A—C13—H13B	109.5	C1—N1—C3	110.2 (3)
C11—C13—H13C	109.5	C4—N1—C3	124.1 (3)
H13A—C13—H13C	109.5	C1—N2—C15	126.6 (3)
H13B—C13—H13C	109.5	C1—N2—C2	110.1 (3)
C11—C13'—H13D	109.5	C15—N2—C2	122.9 (3)
C11—C13'—H13E	109.5	H1A—O1—H1B	120 (5)
N2—C2—C3—N1	−7.2 (3)	C15—C16—C17—C18	179.9 (4)
N1—C4—C5—C10	−155.8 (3)	C16—C17—C18—C19	0.7 (7)
N1—C4—C5—C6	28.6 (4)	C17—C18—C19—C20	−1.2 (6)
C10—C5—C6—C7	−0.8 (5)	C17—C18—C19—C22	−178.0 (4)
C4—C5—C6—C7	174.8 (3)	C18—C19—C20—C21	0.8 (6)
C5—C6—C7—C8	−0.8 (5)	C22—C19—C20—C21	177.6 (4)
C6—C7—C8—C9	1.1 (5)	C17—C16—C21—C20	−0.7 (6)
C6—C7—C8—C11	−178.1 (3)	C15—C16—C21—C20	179.7 (4)
C7—C8—C9—C10	0.2 (5)	C19—C20—C21—C16	0.2 (7)
C11—C8—C9—C10	179.3 (3)	C20—C19—C22—C23	156.2 (4)
C6—C5—C10—C9	2.1 (5)	C18—C19—C22—C23	−27.1 (5)
C4—C5—C10—C9	−173.7 (3)	C20—C19—C22—C24	−83.8 (5)
C8—C9—C10—C5	−1.8 (6)	C18—C19—C22—C24	92.9 (5)
C9—C8—C11—C12	134.6 (5)	C20—C19—C22—C25	35.9 (5)
C7—C8—C11—C12	−46.3 (6)	C18—C19—C22—C25	−147.4 (4)
C9—C8—C11—C12'	77.5 (13)	N2—C1—N1—C4	−170.4 (3)
C7—C8—C11—C12'	−103.5 (13)	N2—C1—N1—C3	−2.6 (4)
C9—C8—C11—C13'	−49.7 (13)	C5—C4—N1—C1	−120.4 (3)
C7—C8—C11—C13'	129.4 (13)	C5—C4—N1—C3	73.4 (4)
C9—C8—C11—C14	−104.8 (5)	C2—C3—N1—C1	6.3 (3)
C7—C8—C11—C14	74.3 (5)	C2—C3—N1—C4	174.2 (3)
C9—C8—C11—C13	13.3 (6)	N1—C1—N2—C15	−175.2 (3)
C7—C8—C11—C13	−167.7 (5)	N1—C1—N2—C2	−2.6 (4)
C9—C8—C11—C14'	−164.9 (9)	C16—C15—N2—C1	−121.4 (4)
C7—C8—C11—C14'	14.2 (10)	C16—C15—N2—C2	66.8 (4)
N2—C15—C16—C21	−130.9 (4)	C3—C2—N2—C1	6.2 (4)
N2—C15—C16—C17	49.5 (5)	C3—C2—N2—C15	179.2 (3)
C21—C16—C17—C18	0.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1i	0.86 (4)	2.36 (4)	3.206 (3)	174 (4)
C3—H3B···O1ii	0.96	2.53	3.304 (4)	138
C17—H17···O1i	0.96	2.47	3.423 (5)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1i	0.86 (4)	2.36 (4)	3.206 (3)	174 (4)
C3—H3B⋯O1ii	0.96	2.53	3.304 (4)	138
C17—H17⋯O1i	0.96	2.47	3.423 (5)	175

Symmetry codes: (i) ; (ii) .