4-Chloro-2-[(2,6-diisopropyl­phen­yl)imino­meth­yl]phenol

Balamurugan, P.; Raja, K.; Easwaramoorthy, D.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S1600536812020612

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1721

doi:10.1107/S1600536812020612

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4-Chloro-2-[(2,6-diisopropylphenyl)iminomethyl]phenol

P. Balamurugan,^a K. Kanmani Raja,^b D. Easwaramoorthy,^c G. Chakkaravarthi ^d ^* and G. Rajagopal ^e ^*

^aDepartment of Chemistry, Government Arts College (Men), Nandanam, Chennai 600 035, India, ^bDepartment of Chemistry, Government Thirumagal Mills College, Gudiyattam 632 604, India, ^cDepartment of Chemistry, B.S. Abdur Rahman University, Vandalur, Chennai 600 049, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 5 May 2012; accepted 7 May 2012; online 16 May 2012)

The asymmetric unit of the title compound, C₁₉H₂₂ClNO, contains two independent molecules in which the dihedral angles between the aromatic rings are 76.45 (9) and 74.69 (9)°. An intramolecular O—H⋯N hydrogen bond occurs in each molecule. The crystal structure features weak C—H⋯π interactions.

Related literature

For the biological activity of Schiff base ligands, see: Santos et al. (2001 ). For related strucutures, see: Raja et al. (2008 ); Lin et al. (2005 ).

Experimental

Crystal data

C₁₉H₂₂ClNO
M_r = 315.83
Triclinic, $[P \overline 1]$
a = 11.276 (2) Å
b = 11.776 (2) Å
c = 14.189 (3) Å
α = 73.01 (3)°
β = 88.42 (2)°
γ = 85.57 (3)°
V = 1796.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.939, T_max = 0.967
40436 measured reflections
8907 independent reflections
5518 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.153
S = 1.02
8907 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C1–C6 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.646 (2)	147
O2—H2⋯N2	0.82	1.90	2.630 (2)	147
C31—H31c⋯Cg1	0.96	2.90	3.743 (3)	147
C12—H12A⋯Cg3ⁱ	0.96	2.98	3.833 (3)	149
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020612/vm2174sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020612/vm2174Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020612/vm2174Isup3.cml

checkCIF report

Comment top

Schiff base derivatives are found to exhibit important pharmacological properties, such as antibacterial, antitumor and antitoxic activities (Santos et al., 2001).

The asymmetric unit of the title compound (I) (Fig. 1) contains two molecules. The geometric parameters in (I) are comparable with the similar reported structures (Raja et al., 2008; Lin et al., 2005). The dihedral angles between the aromatic rings (C1-C6) and (C14-C19) & (C21-C26) and (C33-C38) are 76.45 (9) and 74.69 (9)°, respectively. In the asymmetric unit of (I), both molecules adopt an anti-periplanar conformation [C14-C13-N1-C1 = 176.31 (15)° and C33-C32-N2-C20 = -176.22 (15)°] about the C=N bond.

The molecular structure is stabilized by weak intramolecular O-H···N hydrogen bonds and C-H···π interactions (Table 1). The crystal structure is stabilized by a weak intermolecular C-H···π interaction (Table 1).

Related literature top

For the biological activity of Schiff base ligands, see: Santos et al. (2001). For related strucutures, see: Raja et al. (2008); Lin et al. (2005).

Experimental top

An ethanolic solution (10 ml) of 2,6-diisopropylaniline [2 mmol] was magnetically stirred in a round bottom flask followed by drop wise addition of ethanolic solution (10 ml) of 5-chlorosalicylaldehyde [2 mmol]. The reaction mixture was then refluxed for 3 h and upon cooling to 273 K, a yellow solid precipitated from the reaction mixture. The solid which separated out was filtered, washed with ice cold ethanol and dried over anhydrous CaCl₂. Single crystals of good diffraction quality were obtained by recrystallization of the compound from an ethanol solution by the slow evaporation method.Yield: 70 %.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down b axis. Intramolecular hydrogen bond and C-H···π interactions are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted. [Symmetry code (i) -1 + x, y, z. Cg1 and Cg3 are the centroids of the rings (C1-C6) and (C20-C25)].

4-Chloro-2-[(2,6-diisopropylphenyl)iminomethyl]phenol top

Crystal data top

C₁₉H₂₂ClNO	Z = 4
M_r = 315.83	F(000) = 672
Triclinic, P1	D_x = 1.168 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.276 (2) Å	Cell parameters from 8910 reflections
b = 11.776 (2) Å	θ = 1.5–28.4°
c = 14.189 (3) Å	µ = 0.21 mm⁻¹
α = 73.01 (3)°	T = 295 K
β = 88.42 (2)°	Prism, light yellow
γ = 85.57 (3)°	0.30 × 0.20 × 0.16 mm
V = 1796.5 (6) Å³

Data collection top

Bruker Kappa APEXII diffractometer	8907 independent reflections
Radiation source: fine-focus sealed tube	5518 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.939, T_max = 0.967	k = −15→15
40436 measured reflections	l = −18→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0607P)² + 0.4833P] where P = (F_o² + 2F_c²)/3
8907 reflections	(Δ/σ)_max < 0.001
407 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₂₂ClNO	γ = 85.57 (3)°
M_r = 315.83	V = 1796.5 (6) Å³
Triclinic, P1	Z = 4
a = 11.276 (2) Å	Mo Kα radiation
b = 11.776 (2) Å	µ = 0.21 mm⁻¹
c = 14.189 (3) Å	T = 295 K
α = 73.01 (3)°	0.30 × 0.20 × 0.16 mm
β = 88.42 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	8907 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5518 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.967	R_int = 0.027
40436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
8907 reflections	Δρ_min = −0.36 e Å⁻³
407 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.13739 (14)	0.66107 (15)	0.23173 (12)	0.0498 (4)
C2	0.17448 (14)	0.71891 (15)	0.13594 (13)	0.0509 (4)
C3	0.16389 (16)	0.66098 (16)	0.06416 (14)	0.0584 (4)
H3	0.1890	0.6969	0.0001	0.070*
C4	0.11715 (18)	0.55202 (17)	0.08624 (15)	0.0652 (5)
H4	0.1117	0.5143	0.0375	0.078*
C5	0.07837 (18)	0.49844 (17)	0.18045 (15)	0.0658 (5)
H5	0.0457	0.4251	0.1944	0.079*
C6	0.08694 (16)	0.55152 (16)	0.25501 (13)	0.0572 (4)
C7	0.22149 (17)	0.84165 (16)	0.10807 (14)	0.0602 (5)
H7	0.2122	0.8713	0.1658	0.072*
C8	0.1505 (3)	0.9267 (2)	0.0261 (3)	0.1324 (13)
H8A	0.1773	1.0052	0.0141	0.199*
H8B	0.0679	0.9276	0.0444	0.199*
H8C	0.1608	0.9020	−0.0325	0.199*
C9	0.3505 (2)	0.8389 (3)	0.0819 (3)	0.1291 (12)
H9A	0.3952	0.7883	0.1370	0.194*
H9B	0.3767	0.9180	0.0657	0.194*
H9C	0.3627	0.8085	0.0263	0.194*
C10	0.0474 (2)	0.48956 (19)	0.35955 (15)	0.0753 (6)
H10	0.0405	0.5493	0.3955	0.090*
C11	0.1404 (3)	0.3948 (3)	0.4105 (2)	0.1328 (12)
H11A	0.1499	0.3350	0.3766	0.199*
H11B	0.1161	0.3591	0.4773	0.199*
H11C	0.2146	0.4297	0.4101	0.199*
C12	−0.0733 (2)	0.4395 (2)	0.3639 (2)	0.0987 (8)
H12A	−0.1291	0.4996	0.3252	0.148*
H12B	−0.1005	0.4148	0.4310	0.148*
H12C	−0.0668	0.3723	0.3382	0.148*
C13	0.24570 (16)	0.71952 (15)	0.34528 (13)	0.0543 (4)
H13	0.3115	0.6794	0.3255	0.065*
C14	0.26162 (16)	0.78161 (15)	0.41832 (12)	0.0517 (4)
C15	0.16653 (17)	0.84406 (16)	0.45179 (13)	0.0577 (4)
C16	0.1866 (2)	0.9024 (2)	0.52119 (15)	0.0752 (6)
H16	0.1238	0.9438	0.5436	0.090*
C17	0.2994 (2)	0.8991 (2)	0.55676 (15)	0.0798 (7)
H17	0.3126	0.9380	0.6035	0.096*
C18	0.3930 (2)	0.83857 (18)	0.52351 (14)	0.0691 (6)
C19	0.37495 (18)	0.78031 (16)	0.45505 (14)	0.0613 (5)
H19	0.4388	0.7397	0.4331	0.074*
C38	0.89501 (17)	0.76937 (15)	−0.08837 (13)	0.0574 (4)
H38	0.9565	0.7309	−0.0459	0.069*
C20	0.63784 (14)	0.65812 (15)	0.19237 (12)	0.0500 (4)
C21	0.58671 (16)	0.54870 (16)	0.22519 (14)	0.0590 (4)
C22	0.57451 (18)	0.49846 (18)	0.32620 (15)	0.0683 (5)
H22	0.5417	0.4253	0.3498	0.082*
C23	0.60990 (18)	0.55449 (19)	0.39185 (15)	0.0693 (5)
H23	0.6033	0.5181	0.4592	0.083*
C24	0.65504 (17)	0.66414 (18)	0.35815 (14)	0.0637 (5)
H24	0.6762	0.7026	0.4032	0.076*
C25	0.66973 (15)	0.71898 (16)	0.25773 (13)	0.0541 (4)
C26	0.71529 (19)	0.84265 (17)	0.22278 (15)	0.0676 (5)
H26	0.7221	0.8639	0.1508	0.081*
C27	0.6271 (3)	0.9335 (2)	0.2472 (2)	0.1123 (9)
H27A	0.6172	0.9144	0.3174	0.169*
H27B	0.5520	0.9325	0.2173	0.169*
H27C	0.6562	1.0112	0.2224	0.169*
C28	0.8359 (3)	0.8457 (3)	0.2619 (3)	0.1506 (16)
H28A	0.8322	0.8263	0.3324	0.226*
H28B	0.8633	0.9239	0.2352	0.226*
H28C	0.8899	0.7887	0.2432	0.226*
C29	0.5491 (2)	0.4852 (2)	0.15336 (17)	0.0784 (6)
H29	0.5484	0.5422	0.0873	0.094*
C30	0.6386 (3)	0.3834 (3)	0.1526 (3)	0.1459 (15)
H30A	0.7165	0.4123	0.1399	0.219*
H30B	0.6184	0.3493	0.1020	0.219*
H30C	0.6378	0.3239	0.2154	0.219*
C31	0.4257 (2)	0.4417 (2)	0.1744 (2)	0.0997 (8)
H31A	0.4262	0.3787	0.2353	0.150*
H31B	0.4019	0.4125	0.1219	0.150*
H31C	0.3708	0.5061	0.1795	0.150*
C32	0.75544 (15)	0.71162 (14)	0.05083 (12)	0.0505 (4)
H32	0.8191	0.6740	0.0912	0.061*
C33	0.77830 (15)	0.76946 (14)	−0.05304 (12)	0.0496 (4)
C34	0.68686 (18)	0.82811 (16)	−0.11783 (13)	0.0607 (5)
C35	0.7139 (2)	0.8834 (2)	−0.21581 (16)	0.0809 (6)
H35	0.6533	0.9218	−0.2594	0.097*
C36	0.8297 (2)	0.88172 (19)	−0.24875 (15)	0.0791 (6)
H36	0.8472	0.9190	−0.3145	0.095*
C37	0.91965 (19)	0.82525 (17)	−0.18488 (15)	0.0647 (5)
Cl1	0.53583 (7)	0.83560 (6)	0.56803 (5)	0.1042 (3)
Cl2	1.06620 (6)	0.82311 (6)	−0.22699 (5)	0.0990 (2)
N1	0.14538 (13)	0.71810 (13)	0.30767 (11)	0.0546 (3)
N2	0.65162 (12)	0.71064 (12)	0.08848 (10)	0.0528 (3)
O1	0.05522 (12)	0.85034 (14)	0.41805 (11)	0.0753 (4)
H1	0.0543	0.8131	0.3775	0.113*
O2	0.57289 (13)	0.83301 (16)	−0.08738 (11)	0.0832 (4)
H2	0.5687	0.7966	−0.0287	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0504 (9)	0.0495 (9)	0.0544 (10)	−0.0034 (7)	−0.0043 (7)	−0.0226 (8)
C2	0.0494 (9)	0.0491 (9)	0.0567 (10)	−0.0026 (7)	−0.0023 (7)	−0.0196 (8)
C3	0.0671 (11)	0.0584 (11)	0.0526 (10)	−0.0031 (8)	−0.0008 (8)	−0.0210 (9)
C4	0.0814 (13)	0.0597 (11)	0.0642 (12)	−0.0053 (9)	−0.0102 (10)	−0.0325 (10)
C5	0.0825 (13)	0.0528 (10)	0.0684 (13)	−0.0161 (9)	−0.0052 (10)	−0.0241 (10)
C6	0.0649 (10)	0.0529 (10)	0.0575 (11)	−0.0108 (8)	−0.0024 (8)	−0.0199 (8)
C7	0.0686 (11)	0.0555 (10)	0.0603 (11)	−0.0140 (8)	0.0046 (9)	−0.0209 (9)
C8	0.147 (3)	0.0542 (14)	0.179 (3)	−0.0117 (15)	−0.063 (2)	−0.0002 (17)
C9	0.0758 (17)	0.096 (2)	0.216 (4)	−0.0333 (14)	0.026 (2)	−0.042 (2)
C10	0.0984 (16)	0.0677 (13)	0.0634 (12)	−0.0279 (11)	0.0082 (11)	−0.0199 (10)
C11	0.120 (2)	0.154 (3)	0.085 (2)	−0.005 (2)	−0.0113 (17)	0.0267 (19)
C12	0.0974 (18)	0.0964 (18)	0.1012 (19)	−0.0333 (14)	0.0262 (15)	−0.0225 (15)
C13	0.0599 (10)	0.0517 (10)	0.0543 (10)	−0.0074 (8)	−0.0005 (8)	−0.0192 (8)
C14	0.0655 (10)	0.0471 (9)	0.0436 (9)	−0.0151 (8)	−0.0012 (7)	−0.0117 (7)
C15	0.0745 (12)	0.0549 (10)	0.0449 (9)	−0.0179 (9)	0.0066 (8)	−0.0135 (8)
C16	0.0992 (16)	0.0766 (14)	0.0590 (12)	−0.0182 (12)	0.0127 (11)	−0.0321 (11)
C17	0.123 (2)	0.0747 (14)	0.0514 (12)	−0.0334 (14)	−0.0014 (12)	−0.0264 (11)
C18	0.0927 (15)	0.0597 (11)	0.0539 (11)	−0.0296 (11)	−0.0161 (10)	−0.0074 (9)
C19	0.0732 (12)	0.0546 (10)	0.0566 (11)	−0.0150 (9)	−0.0072 (9)	−0.0137 (9)
C38	0.0677 (11)	0.0507 (10)	0.0536 (10)	−0.0117 (8)	0.0064 (8)	−0.0135 (8)
C20	0.0473 (8)	0.0520 (9)	0.0467 (9)	−0.0048 (7)	0.0039 (7)	−0.0083 (7)
C21	0.0625 (11)	0.0558 (10)	0.0569 (11)	−0.0118 (8)	0.0061 (8)	−0.0122 (8)
C22	0.0752 (13)	0.0607 (12)	0.0636 (12)	−0.0174 (9)	0.0121 (10)	−0.0075 (10)
C23	0.0752 (13)	0.0746 (13)	0.0493 (11)	−0.0099 (10)	0.0096 (9)	−0.0039 (10)
C24	0.0684 (11)	0.0714 (12)	0.0529 (11)	−0.0073 (9)	0.0014 (8)	−0.0202 (9)
C25	0.0543 (9)	0.0543 (10)	0.0519 (10)	−0.0061 (7)	0.0014 (7)	−0.0125 (8)
C26	0.0854 (14)	0.0578 (11)	0.0624 (12)	−0.0177 (10)	0.0006 (10)	−0.0189 (9)
C27	0.140 (3)	0.0686 (16)	0.131 (2)	−0.0010 (16)	−0.008 (2)	−0.0328 (16)
C28	0.100 (2)	0.100 (2)	0.230 (4)	−0.0460 (17)	−0.046 (2)	0.000 (2)
C29	0.1006 (16)	0.0690 (13)	0.0709 (13)	−0.0313 (12)	0.0087 (12)	−0.0230 (11)
C30	0.098 (2)	0.178 (3)	0.218 (4)	−0.007 (2)	0.016 (2)	−0.148 (3)
C31	0.0865 (17)	0.0907 (17)	0.130 (2)	−0.0159 (13)	−0.0193 (15)	−0.0411 (16)
C32	0.0564 (9)	0.0456 (9)	0.0465 (9)	−0.0060 (7)	−0.0013 (7)	−0.0081 (7)
C33	0.0615 (10)	0.0412 (8)	0.0466 (9)	−0.0098 (7)	0.0019 (7)	−0.0122 (7)
C34	0.0724 (12)	0.0570 (11)	0.0516 (10)	−0.0075 (9)	−0.0044 (9)	−0.0130 (8)
C35	0.1028 (17)	0.0781 (15)	0.0524 (12)	0.0004 (12)	−0.0126 (11)	−0.0053 (10)
C36	0.122 (2)	0.0659 (13)	0.0458 (11)	−0.0168 (13)	0.0152 (12)	−0.0093 (10)
C37	0.0876 (13)	0.0505 (10)	0.0587 (11)	−0.0206 (9)	0.0217 (10)	−0.0183 (9)
Cl1	0.1159 (5)	0.1021 (5)	0.0971 (5)	−0.0390 (4)	−0.0434 (4)	−0.0211 (4)
Cl2	0.1058 (5)	0.1024 (5)	0.0922 (4)	−0.0357 (4)	0.0498 (4)	−0.0310 (4)
N1	0.0585 (8)	0.0561 (8)	0.0556 (9)	−0.0110 (6)	−0.0003 (6)	−0.0244 (7)
N2	0.0563 (8)	0.0521 (8)	0.0480 (8)	−0.0085 (6)	0.0024 (6)	−0.0107 (6)
O1	0.0675 (8)	0.0914 (11)	0.0773 (10)	−0.0064 (7)	0.0050 (7)	−0.0413 (8)
O2	0.0667 (9)	0.1046 (12)	0.0678 (9)	0.0040 (8)	−0.0107 (7)	−0.0104 (9)

Geometric parameters (Å, º) top

C1—C6	1.397 (2)	C38—C33	1.395 (2)
C1—C2	1.399 (2)	C38—H38	0.9300
C1—N1	1.435 (2)	C20—C25	1.396 (2)
C2—C3	1.394 (2)	C20—C21	1.400 (2)
C2—C7	1.516 (2)	C20—N2	1.431 (2)
C3—C4	1.372 (3)	C21—C22	1.389 (3)
C3—H3	0.9300	C21—C29	1.515 (3)
C4—C5	1.376 (3)	C22—C23	1.372 (3)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.386 (3)	C23—C24	1.372 (3)
C5—H5	0.9300	C23—H23	0.9300
C6—C10	1.521 (3)	C24—C25	1.393 (3)
C7—C9	1.492 (3)	C24—H24	0.9300
C7—C8	1.498 (3)	C25—C26	1.520 (3)
C7—H7	0.9800	C26—C28	1.490 (3)
C8—H8A	0.9600	C26—C27	1.512 (3)
C8—H8B	0.9600	C26—H26	0.9800
C8—H8C	0.9600	C27—H27A	0.9600
C9—H9A	0.9600	C27—H27B	0.9600
C9—H9B	0.9600	C27—H27C	0.9600
C9—H9C	0.9600	C28—H28A	0.9600
C10—C11	1.502 (4)	C28—H28B	0.9600
C10—C12	1.517 (3)	C28—H28C	0.9600
C10—H10	0.9800	C29—C30	1.508 (4)
C11—H11A	0.9600	C29—C31	1.511 (3)
C11—H11B	0.9600	C29—H29	0.9800
C11—H11C	0.9600	C30—H30A	0.9600
C12—H12A	0.9600	C30—H30B	0.9600
C12—H12B	0.9600	C30—H30C	0.9600
C12—H12C	0.9600	C31—H31A	0.9600
C13—N1	1.267 (2)	C31—H31B	0.9600
C13—C14	1.454 (2)	C31—H31C	0.9600
C13—H13	0.9300	C32—N2	1.273 (2)
C14—C19	1.391 (2)	C32—C33	1.457 (2)
C14—C15	1.404 (3)	C32—H32	0.9300
C15—O1	1.345 (2)	C33—C34	1.399 (3)
C15—C16	1.388 (3)	C34—O2	1.347 (2)
C16—C17	1.375 (3)	C34—C35	1.388 (3)
C16—H16	0.9300	C35—C36	1.376 (3)
C17—C18	1.377 (3)	C35—H35	0.9300
C17—H17	0.9300	C36—C37	1.373 (3)
C18—C19	1.370 (3)	C36—H36	0.9300
C18—Cl1	1.740 (2)	C37—Cl2	1.743 (2)
C19—H19	0.9300	O1—H1	0.8200
C38—C37	1.366 (3)	O2—H2	0.8200

C6—C1—C2	121.94 (15)	C33—C38—H38	119.7
C6—C1—N1	118.55 (15)	C25—C20—C21	121.75 (16)
C2—C1—N1	119.43 (14)	C25—C20—N2	119.82 (14)
C3—C2—C1	117.57 (15)	C21—C20—N2	118.35 (16)
C3—C2—C7	119.87 (16)	C22—C21—C20	117.72 (17)
C1—C2—C7	122.54 (15)	C22—C21—C29	120.96 (17)
C4—C3—C2	121.24 (17)	C20—C21—C29	121.30 (17)
C4—C3—H3	119.4	C23—C22—C21	121.37 (18)
C2—C3—H3	119.4	C23—C22—H22	119.3
C3—C4—C5	120.05 (17)	C21—C22—H22	119.3
C3—C4—H4	120.0	C22—C23—C24	120.05 (18)
C5—C4—H4	120.0	C22—C23—H23	120.0
C4—C5—C6	121.33 (17)	C24—C23—H23	120.0
C4—C5—H5	119.3	C23—C24—C25	121.25 (18)
C6—C5—H5	119.3	C23—C24—H24	119.4
C5—C6—C1	117.82 (17)	C25—C24—H24	119.4
C5—C6—C10	120.80 (16)	C24—C25—C20	117.73 (16)
C1—C6—C10	121.33 (16)	C24—C25—C26	119.86 (17)
C9—C7—C8	110.6 (2)	C20—C25—C26	122.38 (16)
C9—C7—C2	112.29 (18)	C28—C26—C27	111.8 (2)
C8—C7—C2	111.16 (17)	C28—C26—C25	112.04 (19)
C9—C7—H7	107.5	C27—C26—C25	110.81 (19)
C8—C7—H7	107.5	C28—C26—H26	107.3
C2—C7—H7	107.5	C27—C26—H26	107.3
C7—C8—H8A	109.5	C25—C26—H26	107.3
C7—C8—H8B	109.5	C26—C27—H27A	109.5
H8A—C8—H8B	109.5	C26—C27—H27B	109.5
C7—C8—H8C	109.5	H27A—C27—H27B	109.5
H8A—C8—H8C	109.5	C26—C27—H27C	109.5
H8B—C8—H8C	109.5	H27A—C27—H27C	109.5
C7—C9—H9A	109.5	H27B—C27—H27C	109.5
C7—C9—H9B	109.5	C26—C28—H28A	109.5
H9A—C9—H9B	109.5	C26—C28—H28B	109.5
C7—C9—H9C	109.5	H28A—C28—H28B	109.5
H9A—C9—H9C	109.5	C26—C28—H28C	109.5
H9B—C9—H9C	109.5	H28A—C28—H28C	109.5
C11—C10—C12	111.2 (2)	H28B—C28—H28C	109.5
C11—C10—C6	110.4 (2)	C30—C29—C31	110.5 (2)
C12—C10—C6	112.97 (19)	C30—C29—C21	110.2 (2)
C11—C10—H10	107.3	C31—C29—C21	112.84 (19)
C12—C10—H10	107.3	C30—C29—H29	107.7
C6—C10—H10	107.3	C31—C29—H29	107.7
C10—C11—H11A	109.5	C21—C29—H29	107.7
C10—C11—H11B	109.5	C29—C30—H30A	109.5
H11A—C11—H11B	109.5	C29—C30—H30B	109.5
C10—C11—H11C	109.5	H30A—C30—H30B	109.5
H11A—C11—H11C	109.5	C29—C30—H30C	109.5
H11B—C11—H11C	109.5	H30A—C30—H30C	109.5
C10—C12—H12A	109.5	H30B—C30—H30C	109.5
C10—C12—H12B	109.5	C29—C31—H31A	109.5
H12A—C12—H12B	109.5	C29—C31—H31B	109.5
C10—C12—H12C	109.5	H31A—C31—H31B	109.5
H12A—C12—H12C	109.5	C29—C31—H31C	109.5
H12B—C12—H12C	109.5	H31A—C31—H31C	109.5
N1—C13—C14	122.37 (17)	H31B—C31—H31C	109.5
N1—C13—H13	118.8	N2—C32—C33	122.50 (16)
C14—C13—H13	118.8	N2—C32—H32	118.7
C19—C14—C15	119.09 (16)	C33—C32—H32	118.7
C19—C14—C13	118.86 (17)	C38—C33—C34	119.01 (16)
C15—C14—C13	122.04 (16)	C38—C33—C32	119.15 (16)
O1—C15—C16	118.21 (19)	C34—C33—C32	121.81 (16)
O1—C15—C14	122.01 (16)	O2—C34—C35	118.98 (19)
C16—C15—C14	119.79 (19)	O2—C34—C33	121.58 (16)
C17—C16—C15	119.9 (2)	C35—C34—C33	119.44 (19)
C17—C16—H16	120.0	C36—C35—C34	120.3 (2)
C15—C16—H16	120.0	C36—C35—H35	119.8
C16—C17—C18	120.36 (19)	C34—C35—H35	119.8
C16—C17—H17	119.8	C37—C36—C35	120.21 (19)
C18—C17—H17	119.8	C37—C36—H36	119.9
C19—C18—C17	120.6 (2)	C35—C36—H36	119.9
C19—C18—Cl1	119.25 (19)	C38—C37—C36	120.4 (2)
C17—C18—Cl1	120.18 (16)	C38—C37—Cl2	119.51 (18)
C18—C19—C14	120.3 (2)	C36—C37—Cl2	120.04 (16)
C18—C19—H19	119.9	C13—N1—C1	119.38 (15)
C14—C19—H19	119.9	C32—N2—C20	118.93 (15)
C37—C38—C33	120.55 (19)	C15—O1—H1	109.5
C37—C38—H38	119.7	C34—O2—H2	109.5

C6—C1—C2—C3	−2.6 (2)	N2—C20—C21—C29	1.4 (3)
N1—C1—C2—C3	−179.26 (15)	C20—C21—C22—C23	0.8 (3)
C6—C1—C2—C7	175.68 (16)	C29—C21—C22—C23	179.1 (2)
N1—C1—C2—C7	−1.0 (2)	C21—C22—C23—C24	2.1 (3)
C1—C2—C3—C4	1.0 (3)	C22—C23—C24—C25	−2.2 (3)
C7—C2—C3—C4	−177.32 (17)	C23—C24—C25—C20	−0.5 (3)
C2—C3—C4—C5	0.8 (3)	C23—C24—C25—C26	177.53 (18)
C3—C4—C5—C6	−1.0 (3)	C21—C20—C25—C24	3.4 (3)
C4—C5—C6—C1	−0.6 (3)	N2—C20—C25—C24	−179.81 (16)
C4—C5—C6—C10	−178.0 (2)	C21—C20—C25—C26	−174.56 (17)
C2—C1—C6—C5	2.4 (3)	N2—C20—C25—C26	2.2 (3)
N1—C1—C6—C5	179.10 (16)	C24—C25—C26—C28	60.4 (3)
C2—C1—C6—C10	179.81 (18)	C20—C25—C26—C28	−121.6 (3)
N1—C1—C6—C10	−3.5 (3)	C24—C25—C26—C27	−65.2 (3)
C3—C2—C7—C9	−69.4 (3)	C20—C25—C26—C27	112.7 (2)
C1—C2—C7—C9	112.4 (2)	C22—C21—C29—C30	−75.1 (3)
C3—C2—C7—C8	55.2 (3)	C20—C21—C29—C30	103.2 (3)
C1—C2—C7—C8	−123.0 (2)	C22—C21—C29—C31	49.0 (3)
C5—C6—C10—C11	78.3 (3)	C20—C21—C29—C31	−132.8 (2)
C1—C6—C10—C11	−99.1 (3)	C37—C38—C33—C34	−0.3 (3)
C5—C6—C10—C12	−46.9 (3)	C37—C38—C33—C32	−178.46 (16)
C1—C6—C10—C12	135.7 (2)	N2—C32—C33—C38	178.38 (16)
N1—C13—C14—C19	−179.12 (17)	N2—C32—C33—C34	0.3 (3)
N1—C13—C14—C15	0.0 (3)	C38—C33—C34—O2	−178.73 (17)
C19—C14—C15—O1	178.93 (16)	C32—C33—C34—O2	−0.6 (3)
C13—C14—C15—O1	−0.2 (3)	C38—C33—C34—C35	0.9 (3)
C19—C14—C15—C16	−0.5 (3)	C32—C33—C34—C35	178.98 (17)
C13—C14—C15—C16	−179.62 (17)	O2—C34—C35—C36	178.9 (2)
O1—C15—C16—C17	−179.35 (19)	C33—C34—C35—C36	−0.7 (3)
C14—C15—C16—C17	0.1 (3)	C34—C35—C36—C37	0.0 (3)
C15—C16—C17—C18	0.3 (3)	C33—C38—C37—C36	−0.4 (3)
C16—C17—C18—C19	−0.4 (3)	C33—C38—C37—Cl2	−179.74 (13)
C16—C17—C18—Cl1	179.50 (16)	C35—C36—C37—C38	0.6 (3)
C17—C18—C19—C14	0.0 (3)	C35—C36—C37—Cl2	179.87 (17)
Cl1—C18—C19—C14	−179.91 (14)	C14—C13—N1—C1	176.31 (15)
C15—C14—C19—C18	0.5 (3)	C6—C1—N1—C13	106.50 (19)
C13—C14—C19—C18	179.61 (16)	C2—C1—N1—C13	−76.7 (2)
C25—C20—C21—C22	−3.6 (3)	C33—C32—N2—C20	−176.22 (15)
N2—C20—C21—C22	179.64 (16)	C25—C20—N2—C32	75.3 (2)
C25—C20—C21—C29	178.15 (18)	C21—C20—N2—C32	−107.84 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the C1–C6 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.646 (2)	147
O2—H2···N2	0.82	1.90	2.630 (2)	147
C31—H31c···Cg1	0.96	2.90	3.743 (3)	147
C12—H12A···Cg3ⁱ	0.96	2.98	3.833 (3)	149

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂ClNO
M_r	315.83
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	11.276 (2), 11.776 (2), 14.189 (3)
α, β, γ (°)	73.01 (3), 88.42 (2), 85.57 (3)
V (Å³)	1796.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.939, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	40436, 8907, 5518
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.153, 1.02
No. of reflections	8907
No. of parameters	407
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the C1–C6 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.646 (2)	147
O2—H2···N2	0.82	1.90	2.630 (2)	147
C31—H31c···Cg1	0.96	2.90	3.743 (3)	147
C12—H12A···Cg3ⁱ	0.96	2.98	3.833 (3)	149

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lin, J., Cui, G.-H., Li, J.-R. & Xu, S.-S. (2005). Acta Cryst. E61, o627–o628. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. 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

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Volume 68| Part 6| June 2012| Page o1721

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