2-(2-Bromo-4-chloro­anilino)-2-phenyl­ethanol

Mack, E.T.; Brown, M.J.; Krause, J.A.; Lieberman, D.L.; Pinhas, A.R.

doi:10.1107/S1600536805024244

2-(2-Bromo-4-chloroanilino)-2-phenylethanol

E. T. Mack, M. J. Brown, J. A. Krause, D. L. Lieberman and A. R. Pinhas

The title complex, C₁₄H₁₃BrClNO, adopts a helical motif built up from intermolecular O—H

O interactions with a repeat distance of 8.4 Å. Further assembly of the helices forms a parallel square grid array reminiscent of apolar peptide extended packing motifs.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024244/fl6179sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024244/fl6179Isup2.hkl Contains datablock I

CCDC reference: 283911

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.023
wR factor = 0.061
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br     ..  Cl      ..       3.57 Ang.

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

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

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

2-(2-bromo-4-chloroanilino)-2-phenylethanol top

Crystal data top

C₁₄H₁₃BrClNO	D_x = 1.583 Mg m⁻³
M_r = 326.61	Cu Kα radiation, λ = 1.54178 Å
Tetragonal, I4₁/a	Cell parameters from 8222 reflections
Hall symbol: -I 4ad	θ = 3.5–67.9°
a = 25.5382 (8) Å	µ = 5.78 mm⁻¹
c = 8.4031 (4) Å	T = 150 K
V = 5480.5 (4) Å³	Plate, colorless
Z = 16	0.16 × 0.13 × 0.04 mm
F(000) = 2624

Data collection top

Bruker SMART6000 CCD diffractometer	2492 independent reflections
Radiation source: fine-focus sealed tube	2405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 0.83 pixels mm^-1	θ_max = 67.9°, θ_min = 3.5°
ω scans	h = −29→30
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −30→30
T_min = 0.458, T_max = 0.802	l = −9→10
22328 measured reflections

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)] = 0.023	Hydrogen site location: mixed
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0325P)² + 4.3217P] where P = (F_o² + 2F_c²)/3
2492 reflections	(Δ/σ)_max = 0.001
169 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Special details top

Experimental. A suitable crystal was mounted on the tip of a glass fiber with paratone-N.

The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I).

Note that the absorption correction parameters Tmin and Tmax also reflect beam corrections, etc. As a result, the numerical values for Tmin and Tmax may differ from expected values based solely absorption effects and crystal size.

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
Br	0.363383 (7)	0.053436 (7)	0.50895 (2)	0.03354 (9)
Cl	0.565096 (17)	0.066930 (18)	0.26798 (6)	0.03777 (13)
O1	0.26053 (5)	−0.04825 (5)	0.18627 (16)	0.0299 (3)
H1	0.2699 (9)	−0.0348 (9)	0.110 (3)	0.045*
N2	0.36299 (5)	−0.04612 (5)	0.30811 (18)	0.0256 (3)
H2	0.3391 (8)	−0.0306 (8)	0.345 (2)	0.031*
C1	0.50586 (7)	0.03308 (7)	0.2839 (2)	0.0278 (4)
C2	0.49898 (6)	−0.01237 (6)	0.1972 (2)	0.0267 (3)
H3	0.5265	−0.0253	0.1322	0.032*
C3	0.45182 (6)	−0.03900 (6)	0.2054 (2)	0.0258 (3)
H4	0.4475	−0.0703	0.1459	0.031*
C4	0.41021 (6)	−0.02067 (6)	0.30003 (19)	0.0226 (3)
C5	0.41959 (6)	0.02551 (6)	0.38621 (19)	0.0238 (3)
C6	0.46641 (7)	0.05234 (6)	0.3801 (2)	0.0281 (4)
H5	0.4714	0.0834	0.4406	0.034*
C7	0.34885 (6)	−0.08812 (6)	0.1995 (2)	0.0234 (3)
H6	0.3586	−0.0777	0.0887	0.028*
C8	0.28920 (6)	−0.09573 (6)	0.2084 (2)	0.0265 (3)
H7	0.2784	−0.1212	0.1259	0.032*
H8	0.2801	−0.1107	0.3134	0.032*
C9	0.37582 (6)	−0.13964 (6)	0.2398 (2)	0.0245 (3)
C10	0.39542 (7)	−0.14922 (7)	0.3916 (2)	0.0324 (4)
H9	0.3926	−0.1231	0.4716	0.039*
C11	0.41912 (8)	−0.19688 (8)	0.4268 (2)	0.0390 (4)
H10	0.4326	−0.2030	0.5306	0.047*
C12	0.42320 (7)	−0.23542 (7)	0.3121 (3)	0.0369 (4)
H11	0.4391	−0.2680	0.3370	0.044*
C13	0.40395 (7)	−0.22625 (7)	0.1607 (2)	0.0335 (4)
H12	0.4067	−0.2526	0.0814	0.040*
C14	0.38056 (6)	−0.17848 (6)	0.1243 (2)	0.0286 (4)
H13	0.3677	−0.1723	0.0199	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.03728 (13)	0.02704 (12)	0.03630 (13)	0.00372 (7)	0.00742 (7)	−0.00913 (7)
Cl	0.0282 (2)	0.0375 (2)	0.0477 (3)	−0.01126 (18)	−0.00293 (17)	−0.00175 (18)
O1	0.0243 (6)	0.0299 (6)	0.0354 (7)	0.0047 (5)	0.0051 (5)	0.0047 (5)
N2	0.0216 (7)	0.0229 (7)	0.0322 (8)	0.0003 (5)	0.0049 (6)	−0.0069 (6)
C1	0.0245 (8)	0.0275 (8)	0.0315 (9)	−0.0039 (7)	−0.0048 (7)	0.0045 (7)
C2	0.0225 (8)	0.0264 (8)	0.0314 (9)	0.0021 (6)	0.0005 (7)	0.0010 (7)
C3	0.0252 (8)	0.0219 (8)	0.0303 (8)	0.0015 (6)	0.0001 (7)	−0.0035 (6)
C4	0.0237 (8)	0.0202 (7)	0.0240 (8)	0.0016 (6)	−0.0018 (6)	0.0020 (6)
C5	0.0267 (8)	0.0210 (7)	0.0237 (8)	0.0038 (6)	−0.0001 (6)	−0.0006 (6)
C6	0.0332 (9)	0.0219 (7)	0.0292 (9)	−0.0013 (6)	−0.0061 (7)	−0.0021 (6)
C7	0.0218 (8)	0.0216 (7)	0.0267 (8)	−0.0015 (6)	0.0020 (6)	−0.0022 (6)
C8	0.0228 (8)	0.0242 (8)	0.0325 (9)	−0.0004 (6)	0.0015 (7)	0.0005 (7)
C9	0.0190 (7)	0.0222 (8)	0.0322 (9)	−0.0028 (6)	0.0031 (6)	−0.0007 (6)
C10	0.0356 (9)	0.0308 (9)	0.0307 (9)	0.0033 (7)	0.0029 (7)	−0.0004 (7)
C11	0.0399 (10)	0.0395 (10)	0.0377 (10)	0.0054 (8)	0.0016 (8)	0.0096 (8)
C12	0.0303 (9)	0.0256 (9)	0.0548 (12)	0.0036 (7)	0.0047 (8)	0.0072 (8)
C13	0.0250 (8)	0.0245 (8)	0.0511 (11)	−0.0019 (7)	0.0024 (8)	−0.0079 (8)
C14	0.0218 (8)	0.0276 (8)	0.0364 (9)	−0.0009 (6)	−0.0006 (7)	−0.0062 (7)

Geometric parameters (Å, º) top

Br—C5	1.9060 (16)	C7—C9	1.523 (2)
Cl—C1	1.7475 (17)	C7—C8	1.538 (2)
O1—C8	1.429 (2)	C7—H6	1.0000
O1—H1	0.77 (3)	C8—H7	0.9900
N2—C4	1.372 (2)	C8—H8	0.9900
N2—C7	1.454 (2)	C9—C10	1.392 (3)
N2—H2	0.79 (2)	C9—C14	1.393 (2)
C1—C2	1.382 (2)	C10—C11	1.391 (3)
C1—C6	1.382 (3)	C10—H9	0.9500
C2—C3	1.385 (2)	C11—C12	1.382 (3)
C2—H3	0.9500	C11—H10	0.9500
C3—C4	1.407 (2)	C12—C13	1.384 (3)
C3—H4	0.9500	C12—H11	0.9500
C4—C5	1.404 (2)	C13—C14	1.392 (2)
C5—C6	1.379 (2)	C13—H12	0.9500
C6—H5	0.9500	C14—H13	0.9500

C8—O1—H1	109.3 (18)	C9—C7—H6	109.0
C4—N2—C7	122.47 (14)	C8—C7—H6	109.0
C4—N2—H2	117.4 (14)	O1—C8—C7	113.20 (13)
C7—N2—H2	115.2 (15)	O1—C8—H7	108.9
C2—C1—C6	120.98 (15)	C7—C8—H7	108.9
C2—C1—Cl	119.03 (13)	O1—C8—H8	108.9
C6—C1—Cl	119.98 (13)	C7—C8—H8	108.9
C1—C2—C3	119.79 (15)	H7—C8—H8	107.8
C1—C2—H3	120.1	C10—C9—C14	118.82 (16)
C3—C2—H3	120.1	C10—C9—C7	121.22 (15)
C2—C3—C4	121.43 (15)	C14—C9—C7	119.95 (15)
C2—C3—H4	119.3	C11—C10—C9	120.34 (17)
C4—C3—H4	119.3	C11—C10—H9	119.8
N2—C4—C5	121.49 (14)	C9—C10—H9	119.8
N2—C4—C3	122.29 (14)	C12—C11—C10	120.51 (19)
C5—C4—C3	116.22 (14)	C12—C11—H10	119.7
C6—C5—C4	123.09 (15)	C10—C11—H10	119.7
C6—C5—Br	119.15 (12)	C11—C12—C13	119.61 (17)
C4—C5—Br	117.70 (12)	C11—C12—H11	120.2
C5—C6—C1	118.48 (15)	C13—C12—H11	120.2
C5—C6—H5	120.8	C12—C13—C14	120.16 (17)
C1—C6—H5	120.8	C12—C13—H12	119.9
N2—C7—C9	112.66 (13)	C14—C13—H12	119.9
N2—C7—C8	107.99 (13)	C13—C14—C9	120.54 (17)
C9—C7—C8	109.14 (13)	C13—C14—H13	119.7
N2—C7—H6	109.0	C9—C14—H13	119.7

C6—C1—C2—C3	0.5 (3)	C4—N2—C7—C8	−163.06 (14)
Cl—C1—C2—C3	−178.44 (13)	N2—C7—C8—O1	51.93 (18)
C1—C2—C3—C4	0.3 (3)	C9—C7—C8—O1	174.72 (13)
C7—N2—C4—C5	168.53 (15)	N2—C7—C9—C10	21.4 (2)
C7—N2—C4—C3	−11.3 (2)	C8—C7—C9—C10	−98.51 (18)
C2—C3—C4—N2	179.14 (16)	N2—C7—C9—C14	−159.47 (14)
C2—C3—C4—C5	−0.7 (2)	C8—C7—C9—C14	80.58 (18)
N2—C4—C5—C6	−179.51 (15)	C14—C9—C10—C11	−0.2 (3)
C3—C4—C5—C6	0.3 (2)	C7—C9—C10—C11	178.88 (16)
N2—C4—C5—Br	−2.5 (2)	C9—C10—C11—C12	−0.4 (3)
C3—C4—C5—Br	177.40 (12)	C10—C11—C12—C13	0.6 (3)
C4—C5—C6—C1	0.4 (2)	C11—C12—C13—C14	−0.1 (3)
Br—C5—C6—C1	−176.61 (12)	C12—C13—C14—C9	−0.6 (3)
C2—C1—C6—C5	−0.8 (2)	C10—C9—C14—C13	0.7 (2)
Cl—C1—C6—C5	178.07 (13)	C7—C9—C14—C13	−178.39 (15)
C4—N2—C7—C9	76.32 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.77 (3)	2.00 (3)	2.756 (1)	170 (3)

Symmetry code: (i) −y+1/4, x−1/4, z−1/4.

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2-(2-Bromo-4-chloro­anilino)-2-phenyl­ethanol

Supporting information

Key indicators

checkCIF/PLATON results

2-(2-Bromo-4-chloroanilino)-2-phenylethanol