2-Dibutyl­amino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol

Fun, H.-K.; Yeap, C.S.; Vijesh, A.M.; Isloor, A.M.; Vasudeva, P.K.

doi:10.1107/S1600536810037566

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2624-o2625

doi:10.1107/S1600536810037566

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access

2-Dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § A. M. Vijesh,^b Arun M Isloor ^c and P. K. Vasudeva ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSeQuent Scientific Ltd, No. 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka, 575 011, India, and ^cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 August 2010; accepted 20 September 2010; online 25 September 2010)

In the title compound, C₂₃H₂₉Cl₂NO, the fluorene ring is essentially planar, with a maximum deviation from the mean plane of 0.041 (1) Å. The amine group adopts a pyramidal configuration, the sum of the bond angles being 336.2 (3)°. In the crystal, the molecules are linked into dimers by intermolecular O—H⋯N and C—H⋯O hydrogen bonds. Weak C—H⋯π and π–π [centroid–centroid distance = 3.7544 (7) Å] interactions are also observed.

Related literature

For general background and applications of fluorene derivatives, see: Reinhardt et al. (1998 ); Yao & Belfield (2005 ); Werts et al. (2004 ); Belfield et al. (2009 ); Sun et al. (2009 ); Park et al. (2009 ); Kotaka et al. (2010 ); Wong et al. (2005 ); Beulter et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₂₉Cl₂NO
M_r = 406.37
Triclinic, $[P \overline 1]$
a = 10.0009 (4) Å
b = 10.8847 (4) Å
c = 11.0853 (4) Å
α = 68.161 (1)°
β = 70.999 (1)°
γ = 88.904 (1)°
V = 1051.90 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.34 × 0.28 × 0.20 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.900, T_max = 0.937
19180 measured reflections
6052 independent reflections
5448 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.135
S = 1.15
6052 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C1/C9–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1ⁱ	0.89 (2)	1.99 (2)	2.8762 (13)	175 (2)
C14—H14A⋯O1ⁱ	0.98	2.57	3.1831 (15)	121
C8—H8A⋯Cg2ⁱⁱ	0.97	2.98	3.6293 (13)	126
C22—H22A⋯Cg2ⁱⁱⁱ	0.97	2.82	3.6730 (15)	148
C23—H23B⋯Cg3ⁱ	0.96	2.92	3.7920 (18)	152
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037566/fj2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037566/fj2335Isup2.hkl

checkCIF report

Comment top

The fluorene ring is a π-conjugated system that enables facile synthetic manipulation. The synthesis and characterization of fluorene derivatives have attracted much attention in recent years because of their interesting properties and potential applications in various fields, such as two-photon absorption dyes, fluorescent probes, and light-emitting materials (Reinhardt et al., 1998; Yao & Belfield, 2005; Werts et al., 2004; Belfield et al., 2009; Sun et al., 2009; Park et al., 2009; Kotaka et al., 2010; Wong et al., 2005). Fluorene derivatives are also possess biological activities like antimalerial property (Beulter et al., 2007). These diverse applications of fluorene derivatives led us to explore the crystal structure of the title compound.

In the title compound (Fig. 1), the fluorene ring is essentially coplanar with maximum deviation of 0.041 (1) Å at atom C5. The amine group adopts a pyramidal configuration. In the crystal structure, the molecules are linked into dimers (Fig. 2) by intermolecular O1—H1O1···N1 and C14—H14A···O1 hydrogen bonds (Table 1). Weak C—H···π and π···π interactions are observed. Cg1···Cg3ⁱⁱ of 3.7544 (7) Å. Cg1 is centroid of benzene ring C1–C2/C7–C9.

Related literature top

For general background and applications of fluorene derivatives, see: Reinhardt et al. (1998); Yao & Belfield (2005); Werts et al. (2004); Belfield et al. (2009); Sun et al. (2009); Park et al. (2009); Kotaka et al. (2010); Wong et al. (2005); Beulter et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was recrystallized from acetone. M.p. 352–354 K. The sample was a gift from SeQuent Scientific Ltd., No: 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka, 575 011, India.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, viewed down the a axis showing the molecules link into dimers.

2-Dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol top

Crystal data top

C₂₃H₂₉Cl₂NO	Z = 2
M_r = 406.37	F(000) = 432
Triclinic, P1	D_x = 1.283 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0009 (4) Å	Cell parameters from 9903 reflections
b = 10.8847 (4) Å	θ = 2.8–35.1°
c = 11.0853 (4) Å	µ = 0.32 mm⁻¹
α = 68.161 (1)°	T = 100 K
β = 70.999 (1)°	Block, colourless
γ = 88.904 (1)°	0.34 × 0.28 × 0.20 mm
V = 1051.90 (7) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6052 independent reflections
Radiation source: fine-focus sealed tube	5448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.900, T_max = 0.937	k = −13→15
19180 measured reflections	l = −15→15

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0878P)² + 0.1785P] where P = (F_o² + 2F_c²)/3
6052 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₃H₂₉Cl₂NO	γ = 88.904 (1)°
M_r = 406.37	V = 1051.90 (7) Å³
Triclinic, P1	Z = 2
a = 10.0009 (4) Å	Mo Kα radiation
b = 10.8847 (4) Å	µ = 0.32 mm⁻¹
c = 11.0853 (4) Å	T = 100 K
α = 68.161 (1)°	0.34 × 0.28 × 0.20 mm
β = 70.999 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	6052 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5448 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.937	R_int = 0.025
19180 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.65 e Å⁻³
6052 reflections	Δρ_min = −0.39 e Å⁻³
250 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

	x	y	z	U_iso*/U_eq
Cl1	−0.09361 (3)	0.21897 (3)	0.88976 (3)	0.02143 (10)
Cl2	0.91082 (3)	0.72785 (3)	0.47680 (3)	0.02310 (10)
O1	0.34512 (9)	−0.00277 (8)	0.98844 (9)	0.01700 (17)
N1	0.61607 (10)	0.00676 (9)	0.76424 (10)	0.01474 (18)
C1	0.37158 (11)	0.35655 (11)	0.76122 (11)	0.01307 (19)
C2	0.51590 (11)	0.42961 (11)	0.70234 (11)	0.0137 (2)
C3	0.64840 (12)	0.38878 (11)	0.70641 (12)	0.0157 (2)
H3A	0.6557	0.3002	0.7557	0.019*
C4	0.76946 (12)	0.48193 (12)	0.63599 (12)	0.0174 (2)
H4A	0.8580	0.4555	0.6380	0.021*
C5	0.75782 (12)	0.61409 (12)	0.56297 (12)	0.0170 (2)
C6	0.62725 (12)	0.65831 (11)	0.55809 (11)	0.0168 (2)
H6A	0.6208	0.7472	0.5093	0.020*
C7	0.50725 (12)	0.56512 (11)	0.62855 (11)	0.0147 (2)
C8	0.35494 (12)	0.58751 (11)	0.64065 (12)	0.0166 (2)
H8A	0.3211	0.6472	0.6879	0.020*
H8B	0.3446	0.6239	0.5503	0.020*
C9	0.27675 (11)	0.44936 (11)	0.72460 (11)	0.0143 (2)
C10	0.13297 (12)	0.41040 (12)	0.76341 (11)	0.0161 (2)
H10A	0.0709	0.4719	0.7390	0.019*
C11	0.08464 (11)	0.27561 (12)	0.84032 (12)	0.0160 (2)
C12	0.17583 (11)	0.18198 (11)	0.87841 (11)	0.0154 (2)
H12A	0.1399	0.0928	0.9301	0.019*
C13	0.32054 (11)	0.22131 (11)	0.83943 (11)	0.01356 (19)
C14	0.41897 (11)	0.11665 (11)	0.87700 (11)	0.0141 (2)
H14A	0.4898	0.1530	0.9023	0.017*
C15	0.49599 (12)	0.08479 (11)	0.74948 (12)	0.0154 (2)
H15A	0.4284	0.0352	0.7336	0.018*
H15B	0.5313	0.1676	0.6691	0.018*
C16	0.74550 (12)	0.06358 (12)	0.63995 (12)	0.0162 (2)
H16A	0.8249	0.0192	0.6611	0.019*
H16B	0.7652	0.1569	0.6218	0.019*
C17	0.74054 (12)	0.05380 (12)	0.50737 (12)	0.0188 (2)
H17A	0.7301	−0.0393	0.5209	0.023*
H17B	0.6582	0.0929	0.4878	0.023*
C18	0.87478 (13)	0.12510 (13)	0.38423 (12)	0.0220 (2)
H18A	0.8838	0.2184	0.3702	0.026*
H18B	0.9570	0.0873	0.4053	0.026*
C19	0.87480 (18)	0.11485 (18)	0.25151 (15)	0.0351 (3)
H19A	0.9637	0.1568	0.1791	0.053*
H19B	0.7982	0.1585	0.2259	0.053*
H19C	0.8625	0.0227	0.2655	0.053*
C20	0.57620 (12)	−0.13645 (11)	0.80309 (12)	0.0167 (2)
H20A	0.5521	−0.1476	0.7295	0.020*
H20B	0.4922	−0.1680	0.8859	0.020*
C21	0.69500 (13)	−0.22106 (12)	0.82942 (12)	0.0184 (2)
H21A	0.7679	−0.2082	0.7415	0.022*
H21B	0.7381	−0.1912	0.8820	0.022*
C22	0.64153 (15)	−0.36850 (13)	0.90795 (13)	0.0229 (2)
H22A	0.5982	−0.3982	0.8554	0.027*
H22B	0.5687	−0.3813	0.9959	0.027*
C23	0.7601 (2)	−0.45345 (16)	0.93422 (16)	0.0342 (3)
H23A	0.7230	−0.5460	0.9768	0.051*
H23B	0.7965	−0.4309	0.9944	0.051*
H23C	0.8353	−0.4369	0.8480	0.051*
H1O1	0.359 (2)	0.001 (2)	1.062 (2)	0.036 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01152 (14)	0.02463 (17)	0.02342 (16)	0.00024 (10)	−0.00496 (11)	−0.00501 (12)
Cl2	0.01794 (15)	0.02340 (17)	0.02422 (16)	−0.00603 (11)	−0.00230 (11)	−0.00900 (12)
O1	0.0163 (4)	0.0142 (4)	0.0161 (4)	−0.0002 (3)	−0.0040 (3)	−0.0025 (3)
N1	0.0124 (4)	0.0129 (4)	0.0171 (4)	0.0023 (3)	−0.0027 (3)	−0.0058 (3)
C1	0.0123 (4)	0.0138 (5)	0.0132 (4)	0.0025 (3)	−0.0043 (4)	−0.0055 (4)
C2	0.0134 (5)	0.0145 (5)	0.0139 (4)	0.0019 (4)	−0.0047 (4)	−0.0063 (4)
C3	0.0145 (5)	0.0156 (5)	0.0176 (5)	0.0020 (4)	−0.0061 (4)	−0.0065 (4)
C4	0.0135 (5)	0.0205 (5)	0.0195 (5)	0.0011 (4)	−0.0053 (4)	−0.0095 (4)
C5	0.0152 (5)	0.0194 (5)	0.0157 (5)	−0.0027 (4)	−0.0029 (4)	−0.0078 (4)
C6	0.0184 (5)	0.0150 (5)	0.0161 (5)	0.0000 (4)	−0.0056 (4)	−0.0052 (4)
C7	0.0156 (5)	0.0146 (5)	0.0141 (5)	0.0020 (4)	−0.0048 (4)	−0.0060 (4)
C8	0.0158 (5)	0.0141 (5)	0.0184 (5)	0.0031 (4)	−0.0061 (4)	−0.0045 (4)
C9	0.0139 (5)	0.0147 (5)	0.0145 (5)	0.0034 (4)	−0.0048 (4)	−0.0060 (4)
C10	0.0136 (5)	0.0177 (5)	0.0167 (5)	0.0050 (4)	−0.0057 (4)	−0.0061 (4)
C11	0.0115 (4)	0.0183 (5)	0.0166 (5)	0.0012 (4)	−0.0036 (4)	−0.0061 (4)
C12	0.0126 (5)	0.0153 (5)	0.0162 (5)	0.0016 (4)	−0.0038 (4)	−0.0048 (4)
C13	0.0125 (4)	0.0140 (5)	0.0135 (4)	0.0029 (4)	−0.0038 (4)	−0.0053 (4)
C14	0.0126 (4)	0.0118 (5)	0.0150 (5)	0.0014 (3)	−0.0033 (4)	−0.0034 (4)
C15	0.0138 (5)	0.0147 (5)	0.0173 (5)	0.0033 (4)	−0.0050 (4)	−0.0061 (4)
C16	0.0126 (5)	0.0163 (5)	0.0174 (5)	0.0007 (4)	−0.0021 (4)	−0.0066 (4)
C17	0.0180 (5)	0.0181 (5)	0.0176 (5)	0.0001 (4)	−0.0025 (4)	−0.0070 (4)
C18	0.0179 (5)	0.0252 (6)	0.0183 (5)	0.0014 (4)	−0.0027 (4)	−0.0064 (4)
C19	0.0343 (8)	0.0468 (9)	0.0195 (6)	−0.0015 (6)	−0.0029 (5)	−0.0130 (6)
C20	0.0168 (5)	0.0130 (5)	0.0183 (5)	0.0016 (4)	−0.0042 (4)	−0.0057 (4)
C21	0.0204 (5)	0.0158 (5)	0.0180 (5)	0.0054 (4)	−0.0047 (4)	−0.0073 (4)
C22	0.0339 (7)	0.0158 (5)	0.0187 (5)	0.0064 (5)	−0.0087 (5)	−0.0069 (4)
C23	0.0539 (9)	0.0255 (7)	0.0317 (7)	0.0212 (6)	−0.0222 (7)	−0.0146 (6)

Geometric parameters (Å, º) top

Cl1—C11	1.7358 (11)	C13—C14	1.5202 (15)
Cl2—C5	1.7400 (12)	C14—C15	1.5354 (15)
O1—C14	1.4175 (13)	C14—H14A	0.9800
O1—H1O1	0.89 (2)	C15—H15A	0.9700
N1—C15	1.4751 (14)	C15—H15B	0.9700
N1—C20	1.4788 (14)	C16—C17	1.5290 (16)
N1—C16	1.4805 (14)	C16—H16A	0.9700
C1—C13	1.4037 (15)	C16—H16B	0.9700
C1—C9	1.4119 (14)	C17—C18	1.5252 (16)
C1—C2	1.4785 (15)	C17—H17A	0.9700
C2—C3	1.3989 (15)	C17—H17B	0.9700
C2—C7	1.4127 (15)	C18—C19	1.5162 (19)
C3—C4	1.3950 (16)	C18—H18A	0.9700
C3—H3A	0.9300	C18—H18B	0.9700
C4—C5	1.3881 (17)	C19—H19A	0.9600
C4—H4A	0.9300	C19—H19B	0.9600
C5—C6	1.3936 (16)	C19—H19C	0.9600
C6—C7	1.3878 (15)	C20—C21	1.5261 (16)
C6—H6A	0.9300	C20—H20A	0.9700
C7—C8	1.5082 (15)	C20—H20B	0.9700
C8—C9	1.5062 (16)	C21—C22	1.5197 (17)
C8—H8A	0.9700	C21—H21A	0.9700
C8—H8B	0.9700	C21—H21B	0.9700
C9—C10	1.3847 (15)	C22—C23	1.5259 (19)
C10—C11	1.3932 (16)	C22—H22A	0.9700
C10—H10A	0.9300	C22—H22B	0.9700
C11—C12	1.3941 (15)	C23—H23A	0.9600
C12—C13	1.3940 (15)	C23—H23B	0.9600
C12—H12A	0.9300	C23—H23C	0.9600

C14—O1—H1O1	105.1 (14)	N1—C15—H15A	109.0
C15—N1—C20	111.58 (9)	C14—C15—H15A	109.0
C15—N1—C16	111.49 (9)	N1—C15—H15B	109.0
C20—N1—C16	113.09 (9)	C14—C15—H15B	109.0
C13—C1—C9	119.98 (10)	H15A—C15—H15B	107.8
C13—C1—C2	132.12 (10)	N1—C16—C17	116.53 (9)
C9—C1—C2	107.90 (9)	N1—C16—H16A	108.2
C3—C2—C7	119.17 (10)	C17—C16—H16A	108.2
C3—C2—C1	132.54 (10)	N1—C16—H16B	108.2
C7—C2—C1	108.28 (9)	C17—C16—H16B	108.2
C4—C3—C2	119.50 (11)	H16A—C16—H16B	107.3
C4—C3—H3A	120.2	C18—C17—C16	111.72 (10)
C2—C3—H3A	120.2	C18—C17—H17A	109.3
C5—C4—C3	119.99 (10)	C16—C17—H17A	109.3
C5—C4—H4A	120.0	C18—C17—H17B	109.3
C3—C4—H4A	120.0	C16—C17—H17B	109.3
C4—C5—C6	121.95 (10)	H17A—C17—H17B	107.9
C4—C5—Cl2	118.82 (9)	C19—C18—C17	113.12 (11)
C6—C5—Cl2	119.23 (9)	C19—C18—H18A	109.0
C7—C6—C5	117.74 (10)	C17—C18—H18A	109.0
C7—C6—H6A	121.1	C19—C18—H18B	109.0
C5—C6—H6A	121.1	C17—C18—H18B	109.0
C6—C7—C2	121.64 (10)	H18A—C18—H18B	107.8
C6—C7—C8	128.05 (10)	C18—C19—H19A	109.5
C2—C7—C8	110.31 (10)	C18—C19—H19B	109.5
C9—C8—C7	102.80 (9)	H19A—C19—H19B	109.5
C9—C8—H8A	111.2	C18—C19—H19C	109.5
C7—C8—H8A	111.2	H19A—C19—H19C	109.5
C9—C8—H8B	111.2	H19B—C19—H19C	109.5
C7—C8—H8B	111.2	N1—C20—C21	112.70 (9)
H8A—C8—H8B	109.1	N1—C20—H20A	109.1
C10—C9—C1	121.57 (10)	C21—C20—H20A	109.1
C10—C9—C8	127.77 (10)	N1—C20—H20B	109.1
C1—C9—C8	110.66 (9)	C21—C20—H20B	109.1
C9—C10—C11	117.54 (10)	H20A—C20—H20B	107.8
C9—C10—H10A	121.2	C22—C21—C20	112.38 (10)
C11—C10—H10A	121.2	C22—C21—H21A	109.1
C10—C11—C12	122.07 (10)	C20—C21—H21A	109.1
C10—C11—Cl1	120.11 (9)	C22—C21—H21B	109.1
C12—C11—Cl1	117.81 (9)	C20—C21—H21B	109.1
C13—C12—C11	120.35 (10)	H21A—C21—H21B	107.9
C13—C12—H12A	119.8	C21—C22—C23	112.52 (12)
C11—C12—H12A	119.8	C21—C22—H22A	109.1
C12—C13—C1	118.49 (10)	C23—C22—H22A	109.1
C12—C13—C14	119.41 (10)	C21—C22—H22B	109.1
C1—C13—C14	122.04 (9)	C23—C22—H22B	109.1
O1—C14—C13	112.68 (9)	H22A—C22—H22B	107.8
O1—C14—C15	108.89 (9)	C22—C23—H23A	109.5
C13—C14—C15	108.43 (9)	C22—C23—H23B	109.5
O1—C14—H14A	108.9	H23A—C23—H23B	109.5
C13—C14—H14A	108.9	C22—C23—H23C	109.5
C15—C14—H14A	108.9	H23A—C23—H23C	109.5
N1—C15—C14	112.91 (9)	H23B—C23—H23C	109.5

C13—C1—C2—C3	−0.9 (2)	C9—C10—C11—C12	0.31 (17)
C9—C1—C2—C3	179.75 (11)	C9—C10—C11—Cl1	−178.74 (8)
C13—C1—C2—C7	178.18 (11)	C10—C11—C12—C13	−0.25 (18)
C9—C1—C2—C7	−1.15 (12)	Cl1—C11—C12—C13	178.83 (9)
C7—C2—C3—C4	−0.98 (16)	C11—C12—C13—C1	−0.12 (17)
C1—C2—C3—C4	178.04 (11)	C11—C12—C13—C14	−177.47 (10)
C2—C3—C4—C5	0.21 (17)	C9—C1—C13—C12	0.40 (16)
C3—C4—C5—C6	0.51 (17)	C2—C1—C13—C12	−178.86 (11)
C3—C4—C5—Cl2	179.76 (9)	C9—C1—C13—C14	177.68 (10)
C4—C5—C6—C7	−0.40 (17)	C2—C1—C13—C14	−1.58 (18)
Cl2—C5—C6—C7	−179.66 (8)	C12—C13—C14—O1	−20.91 (14)
C5—C6—C7—C2	−0.40 (16)	C1—C13—C14—O1	161.83 (10)
C5—C6—C7—C8	179.25 (10)	C12—C13—C14—C15	99.69 (11)
C3—C2—C7—C6	1.10 (16)	C1—C13—C14—C15	−77.56 (13)
C1—C2—C7—C6	−178.14 (10)	C20—N1—C15—C14	99.92 (11)
C3—C2—C7—C8	−178.62 (10)	C16—N1—C15—C14	−132.56 (10)
C1—C2—C7—C8	2.15 (12)	O1—C14—C15—N1	−69.47 (11)
C6—C7—C8—C9	178.09 (11)	C13—C14—C15—N1	167.61 (9)
C2—C7—C8—C9	−2.22 (12)	C15—N1—C16—C17	−68.12 (12)
C13—C1—C9—C10	−0.34 (16)	C20—N1—C16—C17	58.58 (13)
C2—C1—C9—C10	179.08 (10)	N1—C16—C17—C18	175.50 (10)
C13—C1—C9—C8	−179.72 (10)	C16—C17—C18—C19	178.77 (12)
C2—C1—C9—C8	−0.29 (12)	C15—N1—C20—C21	−175.79 (9)
C7—C8—C9—C10	−177.83 (11)	C16—N1—C20—C21	57.56 (12)
C7—C8—C9—C1	1.49 (12)	N1—C20—C21—C22	163.47 (10)
C1—C9—C10—C11	−0.01 (17)	C20—C21—C22—C23	179.89 (11)
C8—C9—C10—C11	179.25 (11)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C1/C9–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.89 (2)	1.99 (2)	2.8762 (13)	175 (2)
C14—H14A···O1ⁱ	0.98	2.57	3.1831 (15)	121
C8—H8A···Cg2ⁱⁱ	0.97	2.98	3.6293 (13)	126
C22—H22A···Cg2ⁱⁱⁱ	0.97	2.82	3.6730 (15)	148
C23—H23B···Cg3ⁱ	0.96	2.92	3.7920 (18)	152

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₉Cl₂NO
M_r	406.37
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0009 (4), 10.8847 (4), 11.0853 (4)
α, β, γ (°)	68.161 (1), 70.999 (1), 88.904 (1)
V (Å³)	1051.90 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.34 × 0.28 × 0.20

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.900, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	19180, 6052, 5448
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.135, 1.15
No. of reflections	6052
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.39

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C1/C9–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.89 (2)	1.99 (2)	2.8762 (13)	175 (2)
C14—H14A···O1ⁱ	0.9800	2.5700	3.1831 (15)	121.00
C8—H8A···Cg2ⁱⁱ	0.9700	2.9800	3.6293 (13)	126.00
C22—H22A···Cg2ⁱⁱⁱ	0.9700	2.8200	3.6730 (15)	148.00
C23—H23B···Cg3ⁱ	0.9600	2.9200	3.7920 (18)	152.00

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. CSY also thanks USM for the award of a USM Fellowship. AMV is thankful to the management of SeQuent Scientific Ltd, New Mangalore, India, for their invaluable support and allocation of resources for this work. AMI thankful to the Head of the Department of Chemistry and the Director of the National Institute of Technology-Karnataka, Surathkal, India, for providing research facilities.

References

Belfield, K. D., Bondar, M. V., Yanez, C. O., Herandez, F. E. & Przhonska, O. V. (2009). J. Mater. Chem. 19, 7498–7502. Web of Science CrossRef CAS Google Scholar
Beulter, U., Fuenfschilling, C. & Steinkemper, A. (2007). Org. Process Res. Dev. 11, 341–345. Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kotaka, H., Konishi, G. & Mizuno, K. (2010). Tetrahedron Lett. 51, 181–184. Web of Science CrossRef CAS Google Scholar
Park, K. K., Park, J. W. & Hamilton, A. D. (2009). Org. Biomol. Chem. 7, 4225–4232. Web of Science CrossRef PubMed CAS Google Scholar
Reinhardt, B. A., Brott, L. L., Clarson, S. J., Dillard, A. G., Bhatt, J. C., Kannan, R., Yuan, L., He, G. S. & Prasad, P. N. (1998). Chem. Mater. 10, 1863–1874. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, M., Ding, Y., Zhao, L. & Ma, F. (2009). Chem. Phys. 359, 166–172. Web of Science CrossRef CAS Google Scholar
Werts, M. H. V., Gmouh, S., Mongin, O., Pons, T. & Blanchard-Desce, M. (2004). J. Am. Chem. Soc. 126, 16294–16295. Web of Science CrossRef PubMed CAS Google Scholar
Wong, K., Chen, Y., Lin, Y., Su, H. & Wu, C. (2005). Org. Lett. 7, 5361–5364. Web of Science CrossRef PubMed CAS Google Scholar
Yao, S. & Belfield, K. D. (2005). J. Org. Chem. 70, 5126–5132. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 10| October 2010| Pages o2624-o2625

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