2,4-Di-tert-butyl-6-(4-chloro­phenyl­imino­meth­yl)phenol

Li, J.; Zhao, R.; Ma, C.

doi:10.1107/S1600536807062083

2,4-Di-tert-butyl-6-(4-chlorophenyliminomethyl)phenol

In the title molecule, C₂₁H₂₆ClNO, the two benzene rings make a dihedral angle of 28.5 (5)°. The hydroxy group is involved in an intramolecular O—H

N hydrogen bond. One tert-butyl group exhibits rotational disorder between two orientations in a 0.64:0.36 ratio.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062083/cv2363sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062083/cv2363Isup2.hkl Contains datablock I

CCDC reference: 673098

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.065
wR factor = 0.255
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8'    -   C8      ..       7.42 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C9'    -   C9      ..      19.56 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C9'    -   C10     ..      20.56 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10'   -   C8      ..      11.80 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10'   -   C10     ..      19.12 su

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.255
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently, a number of Schiff-bases have been investigated in terms of their crystallography and coordination chemistry (Garnovskii et al., 1993). In continuation of our studies on Schiff-bases, we now report the synthesized and crystal structure of the title compound (I) (Fig. 1).

All the geometric parameters of (I) are in good agreement with those found in 2-((4-(Trimethylstannylthio)phenylimino)methyl)phenol (Li et al., 2007). The mean planes of the two benzene rings in (I) make a dihedral angle of 28.5 (5)° showing that the Schiff-base ligand adopts a non-planar conformation.

Related literature top

For related a crystal structure, see: Li et al. (2007). For details of the crystallography and coordination chemistry of Schiff base compounds, see: Garnovskii et al. (1993).

Experimental top

The Schiff-base compound was synthesized by the reaction of 3,5-di-t-butyl-2-hydroxybenzaldehyde (0.344 g, 1 mmol) and 4-chloroaniline (0.128 g, 1 mmol) in ethanol solution and stirred under reflux conditions (353 K) for 6 h. When cooled to room temperature the solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.387 g, 82%. m.p. 375–377 K.

Analysis found: C 72.30, H 7.65, N 4.04%; C₂₁H₂₆ClNO requires: C 73.34, H 7.62, N 4.07%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.

2,4-Di-tert-butyl-6-(4-chlorophenyliminomethyl)phenol top

Crystal data top

C₂₁H₂₆ClNO	F(000) = 736
M_r = 343.88	D_x = 1.174 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2391 reflections
a = 17.920 (2) Å	θ = 2.3–26.4°
b = 10.4888 (14) Å	µ = 0.20 mm⁻¹
c = 10.3660 (14) Å	T = 273 K
β = 92.638 (2)°	Block, yellow
V = 1946.4 (4) Å³	0.18 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3452 independent reflections
Radiation source: sealed tube	2335 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
phi and ω scans	θ_max = 25.1°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→21
T_min = 0.964, T_max = 0.976	k = −12→9
10040 measured reflections	l = −12→11

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.255	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.175P)² + 0.475P] where P = (F_o² + 2F_c²)/3
3452 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₁H₂₆ClNO	V = 1946.4 (4) Å³
M_r = 343.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.920 (2) Å	µ = 0.20 mm⁻¹
b = 10.4888 (14) Å	T = 273 K
c = 10.3660 (14) Å	0.18 × 0.15 × 0.12 mm
β = 92.638 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3452 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2335 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.976	R_int = 0.028
10040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.255	H-atom parameters constrained
S = 1.00	Δρ_max = 0.62 e Å⁻³
3452 reflections	Δρ_min = −0.43 e Å⁻³
227 parameters

Special details top

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	Occ. (<1)
Cl1	0.36868 (6)	0.55951 (11)	0.21937 (11)	0.0845 (5)
O1	0.67840 (12)	0.9894 (2)	0.6559 (2)	0.0627 (7)
H1	0.6481	0.9500	0.6095	0.094*
N1	0.61348 (15)	0.7948 (3)	0.5399 (3)	0.0598 (7)
C1	0.73053 (16)	0.9078 (3)	0.7064 (3)	0.0483 (7)
C2	0.72582 (17)	0.7775 (3)	0.6732 (3)	0.0515 (7)
C3	0.77991 (17)	0.6935 (3)	0.7248 (3)	0.0538 (8)
H3	0.7765	0.6075	0.7033	0.065*
C4	0.83794 (16)	0.7334 (3)	0.8062 (3)	0.0498 (7)
C5	0.83960 (17)	0.8633 (3)	0.8370 (3)	0.0500 (7)
H5	0.8782	0.8921	0.8925	0.060*
C6	0.78783 (16)	0.9519 (3)	0.7906 (3)	0.0466 (7)
C7	0.8979 (2)	0.6405 (3)	0.8603 (3)	0.0650 (8)
C8	0.9511 (5)	0.6169 (11)	0.7612 (9)	0.0650 (8)	0.360 (5)
H8A	0.9894	0.5603	0.7944	0.097*	0.360 (5)
H8B	0.9732	0.6961	0.7365	0.097*	0.360 (5)
H8C	0.9257	0.5788	0.6873	0.097*	0.360 (5)
C8'	0.9185 (4)	0.5397 (7)	0.7616 (7)	0.090 (2)	0.640 (5)
H8D	0.9326	0.5808	0.6837	0.135*	0.640 (5)
H8E	0.8762	0.4854	0.7429	0.135*	0.640 (5)
H8F	0.9595	0.4894	0.7961	0.135*	0.640 (5)
C9	0.8550 (5)	0.5117 (9)	0.8926 (10)	0.0650 (8)	0.360 (5)
H9A	0.8491	0.4607	0.8159	0.097*	0.360 (5)
H9B	0.8068	0.5319	0.9237	0.097*	0.360 (5)
H9C	0.8834	0.4650	0.9577	0.097*	0.360 (5)
C9'	0.8727 (5)	0.5791 (9)	0.9789 (7)	0.110 (2)	0.640 (5)
H9D	0.8272	0.5330	0.9593	0.165*	0.640 (5)
H9E	0.8639	0.6431	1.0425	0.165*	0.640 (5)
H9F	0.9104	0.5212	1.0118	0.165*	0.640 (5)
C10	0.9297 (6)	0.6831 (9)	0.9918 (8)	0.0650 (8)	0.360 (5)
H10A	0.9613	0.6172	1.0285	0.097*	0.360 (5)
H10B	0.8895	0.6994	1.0477	0.097*	0.360 (5)
H10C	0.9584	0.7595	0.9823	0.097*	0.360 (5)
C10'	0.9736 (4)	0.7120 (7)	0.8890 (10)	0.111 (2)	0.640 (5)
H10D	1.0120	0.6511	0.9120	0.167*	0.640 (5)
H10E	0.9682	0.7705	0.9591	0.167*	0.640 (5)
H10F	0.9871	0.7580	0.8135	0.167*	0.640 (5)
C11	0.79405 (18)	1.0936 (3)	0.8288 (3)	0.0521 (8)
C12	0.8016 (2)	1.1760 (3)	0.7066 (4)	0.0692 (10)
H12A	0.8469	1.1538	0.6659	0.104*
H12B	0.8031	1.2645	0.7303	0.104*
H12C	0.7597	1.1608	0.6477	0.104*
C13	0.7248 (2)	1.1341 (4)	0.8994 (4)	0.0703 (10)
H13A	0.6811	1.1232	0.8433	0.105*
H13B	0.7293	1.2220	0.9241	0.105*
H13C	0.7204	1.0824	0.9751	0.105*
C14	0.8621 (2)	1.1200 (4)	0.9182 (4)	0.0714 (10)
H14A	0.8585	1.0718	0.9963	0.107*
H14B	0.8643	1.2093	0.9385	0.107*
H14C	0.9066	1.0957	0.8761	0.107*
C15	0.66569 (18)	0.7270 (3)	0.5914 (3)	0.0592 (8)
H15	0.6650	0.6398	0.5753	0.071*
C16	0.55663 (17)	0.7359 (3)	0.4608 (3)	0.0562 (8)
C17	0.56777 (19)	0.6271 (4)	0.3906 (4)	0.0726 (10)
H17	0.6147	0.5892	0.3931	0.087*
C18	0.5100 (2)	0.5734 (4)	0.3162 (4)	0.0768 (11)
H18	0.5182	0.5000	0.2686	0.092*
C19	0.44063 (18)	0.6289 (4)	0.3130 (3)	0.0609 (8)
C20	0.42850 (19)	0.7374 (4)	0.3819 (4)	0.0682 (9)
H20	0.3814	0.7748	0.3794	0.082*
C21	0.48642 (19)	0.7913 (4)	0.4551 (4)	0.0681 (9)
H21	0.4782	0.8657	0.5012	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0689 (7)	0.0875 (8)	0.0941 (8)	−0.0176 (5)	−0.0274 (5)	0.0014 (5)
O1	0.0573 (13)	0.0529 (13)	0.0759 (15)	0.0090 (10)	−0.0178 (12)	0.0024 (11)
N1	0.0537 (16)	0.0618 (17)	0.0626 (17)	0.0002 (13)	−0.0106 (13)	0.0010 (14)
C1	0.0439 (15)	0.0489 (16)	0.0517 (16)	0.0027 (12)	−0.0017 (12)	0.0084 (13)
C2	0.0473 (15)	0.0491 (16)	0.0573 (17)	−0.0008 (13)	−0.0066 (13)	0.0028 (13)
C3	0.0544 (16)	0.0461 (15)	0.0599 (17)	0.0043 (13)	−0.0076 (14)	0.0002 (13)
C4	0.0490 (15)	0.0502 (16)	0.0496 (15)	0.0074 (13)	−0.0050 (13)	0.0008 (13)
C5	0.0488 (15)	0.0525 (16)	0.0479 (15)	0.0018 (13)	−0.0050 (12)	0.0003 (13)
C6	0.0455 (15)	0.0468 (16)	0.0474 (15)	0.0015 (12)	0.0001 (12)	0.0010 (12)
C7	0.0654 (16)	0.0644 (17)	0.0638 (16)	0.0219 (13)	−0.0124 (13)	0.0034 (13)
C8	0.0654 (16)	0.0644 (17)	0.0638 (16)	0.0219 (13)	−0.0124 (13)	0.0034 (13)
C8'	0.094 (4)	0.081 (4)	0.092 (4)	0.032 (3)	−0.023 (3)	−0.020 (3)
C9	0.0654 (16)	0.0644 (17)	0.0638 (16)	0.0219 (13)	−0.0124 (13)	0.0034 (13)
C9'	0.112 (4)	0.129 (5)	0.089 (4)	0.056 (4)	0.012 (4)	0.038 (4)
C10	0.0654 (16)	0.0644 (17)	0.0638 (16)	0.0219 (13)	−0.0124 (13)	0.0034 (13)
C10'	0.072 (4)	0.095 (4)	0.163 (6)	0.022 (3)	−0.039 (4)	−0.001 (4)
C11	0.0601 (18)	0.0444 (16)	0.0517 (17)	0.0007 (13)	0.0001 (14)	−0.0007 (13)
C12	0.085 (2)	0.0534 (19)	0.069 (2)	−0.0085 (17)	0.0026 (19)	0.0078 (16)
C13	0.079 (2)	0.062 (2)	0.070 (2)	0.0080 (18)	0.0105 (19)	−0.0090 (18)
C14	0.076 (2)	0.056 (2)	0.081 (2)	−0.0048 (18)	−0.0125 (19)	−0.0083 (18)
C15	0.0567 (17)	0.0521 (17)	0.0674 (18)	−0.0004 (14)	−0.0126 (15)	0.0029 (15)
C16	0.0470 (16)	0.0616 (18)	0.0589 (17)	0.0021 (14)	−0.0074 (14)	0.0003 (15)
C17	0.0503 (17)	0.089 (2)	0.077 (2)	0.0143 (17)	−0.0123 (16)	−0.0184 (19)
C18	0.064 (2)	0.082 (2)	0.083 (2)	0.0112 (18)	−0.0128 (18)	−0.0247 (19)
C19	0.0508 (17)	0.069 (2)	0.0615 (19)	−0.0052 (15)	−0.0116 (15)	0.0046 (16)
C20	0.0497 (17)	0.071 (2)	0.082 (2)	0.0094 (16)	−0.0143 (17)	−0.0031 (18)
C21	0.0579 (19)	0.065 (2)	0.080 (2)	0.0102 (16)	−0.0149 (17)	−0.0084 (17)

Geometric parameters (Å, º) top

Cl1—C19	1.738 (3)	C9'—H9E	0.9600
O1—C1	1.355 (3)	C9'—H9F	0.9600
O1—H1	0.8200	C10—H10A	0.9600
N1—C15	1.273 (4)	C10—H10B	0.9600
N1—C16	1.420 (4)	C10—H10C	0.9600
C1—C6	1.396 (4)	C10'—H10D	0.9600
C1—C2	1.411 (4)	C10'—H10E	0.9600
C2—C3	1.398 (4)	C10'—H10F	0.9600
C2—C15	1.441 (4)	C11—C14	1.523 (5)
C3—C4	1.373 (4)	C11—C13	1.530 (5)
C3—H3	0.9300	C11—C12	1.544 (5)
C4—C5	1.400 (4)	C12—H12A	0.9600
C4—C7	1.538 (4)	C12—H12B	0.9600
C5—C6	1.384 (4)	C12—H12C	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—C11	1.541 (4)	C13—H13B	0.9600
C7—C8	1.454 (9)	C13—H13C	0.9600
C7—C9'	1.477 (7)	C14—H14A	0.9600
C7—C10	1.520 (9)	C14—H14B	0.9600
C7—C8'	1.528 (7)	C14—H14C	0.9600
C7—C10'	1.566 (7)	C15—H15	0.9300
C7—C9	1.598 (9)	C16—C17	1.373 (5)
C8—H8A	0.9600	C16—C21	1.385 (4)
C8—H8B	0.9600	C17—C18	1.382 (5)
C8—H8C	0.9600	C17—H17	0.9300
C8'—H8D	0.9600	C18—C19	1.372 (5)
C8'—H8E	0.9600	C18—H18	0.9300
C8'—H8F	0.9600	C19—C20	1.366 (5)
C9—H9A	0.9600	C20—C21	1.378 (5)
C9—H9B	0.9600	C20—H20	0.9300
C9—H9C	0.9600	C21—H21	0.9300
C9'—H9D	0.9600

C1—O1—H1	109.5	C7—C10—H10B	109.5
C15—N1—C16	119.5 (3)	H10A—C10—H10B	109.5
O1—C1—C6	120.4 (3)	C7—C10—H10C	109.5
O1—C1—C2	119.0 (3)	H10A—C10—H10C	109.5
C6—C1—C2	120.5 (3)	H10B—C10—H10C	109.5
C3—C2—C1	119.0 (3)	C7—C10'—H10D	109.5
C3—C2—C15	118.7 (3)	C7—C10'—H10E	109.5
C1—C2—C15	122.3 (3)	H10D—C10'—H10E	109.5
C4—C3—C2	122.4 (3)	C7—C10'—H10F	109.5
C4—C3—H3	118.8	H10D—C10'—H10F	109.5
C2—C3—H3	118.8	H10E—C10'—H10F	109.5
C3—C4—C5	116.4 (3)	C14—C11—C13	107.7 (3)
C3—C4—C7	121.9 (3)	C14—C11—C6	112.2 (3)
C5—C4—C7	121.8 (3)	C13—C11—C6	109.9 (3)
C6—C5—C4	124.6 (3)	C14—C11—C12	107.4 (3)
C6—C5—H5	117.7	C13—C11—C12	110.0 (3)
C4—C5—H5	117.7	C6—C11—C12	109.7 (3)
C5—C6—C1	117.2 (3)	C11—C12—H12A	109.5
C5—C6—C11	121.3 (3)	C11—C12—H12B	109.5
C1—C6—C11	121.5 (3)	H12A—C12—H12B	109.5
C8—C7—C10	117.0 (6)	C11—C12—H12C	109.5
C9'—C7—C8'	110.4 (5)	H12A—C12—H12C	109.5
C8—C7—C4	108.6 (4)	H12B—C12—H12C	109.5
C9'—C7—C4	110.1 (4)	C11—C13—H13A	109.5
C10—C7—C4	111.6 (4)	C11—C13—H13B	109.5
C8'—C7—C4	112.3 (3)	H13A—C13—H13B	109.5
C9'—C7—C10'	110.3 (5)	C11—C13—H13C	109.5
C8'—C7—C10'	103.0 (5)	H13A—C13—H13C	109.5
C4—C7—C10'	110.6 (4)	H13B—C13—H13C	109.5
C8—C7—C9	110.0 (6)	C11—C14—H14A	109.5
C10—C7—C9	103.0 (6)	C11—C14—H14B	109.5
C4—C7—C9	106.1 (4)	H14A—C14—H14B	109.5
C7—C8—H8A	109.5	C11—C14—H14C	109.5
C7—C8—H8B	109.5	H14A—C14—H14C	109.5
H8A—C8—H8B	109.5	H14B—C14—H14C	109.5
C7—C8—H8C	109.5	N1—C15—C2	123.8 (3)
H8A—C8—H8C	109.5	N1—C15—H15	118.1
H8B—C8—H8C	109.5	C2—C15—H15	118.1
C7—C8'—H8D	109.5	C17—C16—C21	118.7 (3)
C7—C8'—H8E	109.5	C17—C16—N1	123.4 (3)
H8D—C8'—H8E	109.5	C21—C16—N1	117.9 (3)
C7—C8'—H8F	109.5	C16—C17—C18	120.7 (3)
H8D—C8'—H8F	109.5	C16—C17—H17	119.6
H8E—C8'—H8F	109.5	C18—C17—H17	119.6
C7—C9—H9A	109.5	C19—C18—C17	119.7 (4)
C7—C9—H9B	109.5	C19—C18—H18	120.2
H9A—C9—H9B	109.5	C17—C18—H18	120.2
C7—C9—H9C	109.5	C20—C19—C18	120.4 (3)
H9A—C9—H9C	109.5	C20—C19—Cl1	120.6 (3)
H9B—C9—H9C	109.5	C18—C19—Cl1	119.0 (3)
C7—C9'—H9D	109.5	C19—C20—C21	119.7 (3)
C7—C9'—H9E	109.5	C19—C20—H20	120.2
H9D—C9'—H9E	109.5	C21—C20—H20	120.2
C7—C9'—H9F	109.5	C20—C21—C16	120.8 (3)
H9D—C9'—H9F	109.5	C20—C21—H21	119.6
H9E—C9'—H9F	109.5	C16—C21—H21	119.6
C7—C10—H10A	109.5

O1—C1—C2—C3	179.6 (3)	C5—C4—C7—C10'	−28.0 (6)
C6—C1—C2—C3	−0.7 (5)	C3—C4—C7—C9	−39.1 (6)
O1—C1—C2—C15	−2.6 (5)	C5—C4—C7—C9	141.0 (5)
C6—C1—C2—C15	177.1 (3)	C5—C6—C11—C14	0.8 (4)
C1—C2—C3—C4	−0.5 (5)	C1—C6—C11—C14	−178.3 (3)
C15—C2—C3—C4	−178.4 (3)	C5—C6—C11—C13	−119.0 (3)
C2—C3—C4—C5	1.1 (5)	C1—C6—C11—C13	62.0 (4)
C2—C3—C4—C7	−178.8 (3)	C5—C6—C11—C12	120.0 (3)
C3—C4—C5—C6	−0.5 (5)	C1—C6—C11—C12	−59.0 (4)
C7—C4—C5—C6	179.3 (3)	C16—N1—C15—C2	−179.9 (3)
C4—C5—C6—C1	−0.5 (5)	C3—C2—C15—N1	179.7 (3)
C4—C5—C6—C11	−179.6 (3)	C1—C2—C15—N1	1.9 (5)
O1—C1—C6—C5	−179.1 (3)	C15—N1—C16—C17	−29.1 (5)
C2—C1—C6—C5	1.1 (4)	C15—N1—C16—C21	150.7 (3)
O1—C1—C6—C11	0.0 (4)	C21—C16—C17—C18	−0.4 (6)
C2—C1—C6—C11	−179.8 (3)	N1—C16—C17—C18	179.4 (4)
C3—C4—C7—C8	79.1 (6)	C16—C17—C18—C19	−0.3 (7)
C5—C4—C7—C8	−100.8 (6)	C17—C18—C19—C20	0.6 (6)
C3—C4—C7—C9'	−86.0 (6)	C17—C18—C19—Cl1	−179.8 (3)
C5—C4—C7—C9'	94.2 (6)	C18—C19—C20—C21	0.0 (6)
C3—C4—C7—C10	−150.5 (6)	Cl1—C19—C20—C21	−179.7 (3)
C5—C4—C7—C10	29.6 (6)	C19—C20—C21—C16	−0.7 (6)
C3—C4—C7—C8'	37.4 (6)	C17—C16—C21—C20	1.0 (6)
C5—C4—C7—C8'	−142.4 (5)	N1—C16—C21—C20	−178.9 (3)
C3—C4—C7—C10'	151.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.615 (4)	150

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆ClNO
M_r	343.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	17.920 (2), 10.4888 (14), 10.3660 (14)
β (°)	92.638 (2)
V (Å³)	1946.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.18 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	10040, 3452, 2335
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.255, 1.00
No. of reflections	3452
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.43

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).