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The title compound, C23H21Cl2NO, was prepared by condensation of 1,2,3,4-tetra­hydro­naphthalen-1-amine with (3,5-dichloro-2-hydroxy­phen­yl)(phen­yl)methanone. There is an intra­molecular O—H...N hydrogen bond and mol­ecules are linked via N—H...Cl hydrogen bonds, forming centrosymmetric dimers in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044047/ob2082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044047/ob2082Isup2.hkl
Contains datablock I

CCDC reference: 628035

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.005 Å
  • R factor = 0.044
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

(±)-2,4-Dichloro-6-{(RS)-phenyl[(1RS)-1,2,3,4- tetrahydronaphthalen-1-ylamino]methyl}phenol top
Crystal data top
C23H21Cl2NOZ = 2
Mr = 398.31F(000) = 416
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Melting point = 475–476 K
a = 9.3022 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0796 (8) ÅCell parameters from 1646 reflections
c = 12.4308 (16) Åθ = 2.5–23.9°
α = 106.943 (2)°µ = 0.34 mm1
β = 107.763 (2)°T = 298 K
γ = 103.657 (2)°Block, colourless
V = 991.92 (17) Å30.55 × 0.23 × 0.15 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3464 independent reflections
Radiation source: fine-focus sealed tube2599 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1110
Tmin = 0.785, Tmax = 0.951k = 811
5083 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.045P]
where P = (Fo2 + 2Fc2)/3
3464 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
Cl10.29306 (8)0.08850 (7)0.21970 (6)0.0628 (2)
Cl20.89436 (9)0.28816 (10)0.36061 (7)0.0841 (3)
O10.30884 (19)0.1060 (2)0.44869 (16)0.0615 (5)
H10.31680.16400.51400.092*
N10.4687 (2)0.2926 (2)0.67570 (17)0.0462 (5)
H1A0.53640.24880.71120.055*
C10.4469 (3)0.1510 (3)0.4334 (2)0.0465 (6)
C20.4592 (3)0.0672 (3)0.3281 (2)0.0468 (6)
C30.5960 (3)0.1070 (3)0.3054 (2)0.0525 (6)
H30.60270.04850.23510.063*
C40.7217 (3)0.2352 (3)0.3893 (2)0.0548 (6)
C50.7133 (3)0.3232 (3)0.4940 (2)0.0513 (6)
H50.79970.41020.54900.062*
C60.5758 (3)0.2823 (3)0.5176 (2)0.0443 (5)
C70.5551 (3)0.3841 (3)0.6254 (2)0.0455 (5)
H70.48220.43080.59040.055*
C80.7087 (3)0.5103 (3)0.7211 (2)0.0446 (5)
C90.7285 (3)0.6535 (3)0.7344 (2)0.0593 (7)
H90.64600.67300.68440.071*
C100.8679 (4)0.7702 (3)0.8200 (3)0.0742 (8)
H100.87910.86670.82640.089*
C110.9891 (4)0.7437 (3)0.8950 (3)0.0696 (8)
H111.08240.82230.95350.084*
C120.9732 (3)0.6012 (4)0.8839 (3)0.0724 (9)
H121.05590.58290.93490.087*
C130.8337 (3)0.4842 (3)0.7967 (3)0.0648 (7)
H130.82390.38750.78880.078*
C140.4045 (3)0.3720 (3)0.7611 (2)0.0512 (6)
H140.47840.47540.80700.061*
C150.2378 (4)0.3694 (4)0.6881 (3)0.0772 (9)
H15A0.21150.44390.74000.093*
H15B0.24050.39450.61890.093*
C160.1074 (3)0.2183 (4)0.6413 (3)0.0875 (11)
H16A0.00430.21970.59290.105*
H16B0.13270.14360.58860.105*
C170.0953 (4)0.1791 (4)0.7455 (3)0.0897 (11)
H17A0.02780.07540.71360.108*
H17B0.04280.23780.78480.108*
C180.2564 (3)0.2044 (3)0.8403 (3)0.0619 (7)
C190.2627 (4)0.1360 (4)0.9235 (3)0.0805 (9)
H190.16720.07300.91750.097*
C200.4053 (5)0.1593 (4)1.0132 (3)0.0868 (10)
H200.40640.11111.06670.104*
C210.5468 (4)0.2531 (4)1.0248 (3)0.0767 (9)
H210.64410.26971.08640.092*
C220.5442 (3)0.3228 (3)0.9446 (2)0.0578 (7)
H220.64060.38760.95340.069*
C230.4001 (3)0.2986 (3)0.8503 (2)0.0475 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0575 (4)0.0520 (4)0.0568 (4)0.0150 (3)0.0133 (3)0.0057 (3)
Cl20.0654 (5)0.1108 (7)0.0754 (5)0.0164 (4)0.0438 (4)0.0311 (5)
O10.0427 (10)0.0640 (11)0.0568 (11)0.0052 (8)0.0207 (8)0.0057 (9)
N10.0436 (11)0.0490 (11)0.0467 (11)0.0158 (9)0.0205 (9)0.0179 (9)
C10.0394 (12)0.0519 (14)0.0452 (13)0.0163 (11)0.0137 (10)0.0184 (11)
C20.0464 (13)0.0460 (13)0.0434 (13)0.0181 (11)0.0129 (10)0.0155 (11)
C30.0548 (15)0.0605 (16)0.0449 (13)0.0254 (13)0.0204 (12)0.0201 (12)
C40.0497 (14)0.0725 (17)0.0513 (14)0.0214 (13)0.0264 (12)0.0306 (13)
C50.0448 (13)0.0544 (15)0.0477 (14)0.0111 (11)0.0154 (11)0.0193 (12)
C60.0435 (12)0.0482 (13)0.0403 (12)0.0158 (10)0.0153 (10)0.0182 (10)
C70.0421 (12)0.0465 (13)0.0449 (13)0.0138 (10)0.0151 (10)0.0181 (11)
C80.0421 (12)0.0497 (14)0.0401 (12)0.0133 (10)0.0163 (10)0.0181 (10)
C90.0572 (15)0.0533 (16)0.0628 (16)0.0201 (12)0.0174 (13)0.0236 (13)
C100.073 (2)0.0434 (15)0.089 (2)0.0118 (14)0.0256 (18)0.0160 (15)
C110.0591 (17)0.0646 (19)0.0528 (15)0.0050 (14)0.0149 (13)0.0092 (13)
C120.0458 (15)0.091 (2)0.0654 (17)0.0079 (14)0.0054 (13)0.0419 (17)
C130.0484 (15)0.0601 (16)0.0768 (18)0.0114 (13)0.0119 (13)0.0349 (14)
C140.0476 (14)0.0519 (14)0.0562 (14)0.0183 (11)0.0262 (12)0.0177 (12)
C150.0671 (19)0.107 (3)0.088 (2)0.0507 (19)0.0383 (17)0.056 (2)
C160.0432 (16)0.136 (3)0.082 (2)0.0325 (19)0.0189 (15)0.046 (2)
C170.0454 (16)0.121 (3)0.099 (2)0.0170 (17)0.0271 (17)0.051 (2)
C180.0527 (15)0.0694 (18)0.0667 (17)0.0182 (13)0.0313 (14)0.0261 (14)
C190.078 (2)0.092 (2)0.084 (2)0.0211 (18)0.0455 (19)0.0447 (19)
C200.106 (3)0.104 (3)0.077 (2)0.044 (2)0.052 (2)0.051 (2)
C210.077 (2)0.105 (2)0.0488 (16)0.0444 (19)0.0225 (15)0.0243 (17)
C220.0524 (14)0.0647 (16)0.0465 (14)0.0189 (13)0.0199 (12)0.0104 (12)
C230.0471 (13)0.0502 (14)0.0463 (13)0.0208 (11)0.0237 (11)0.0124 (11)
Geometric parameters (Å, º) top
Cl1—C21.737 (2)C12—C131.387 (4)
Cl2—C41.745 (2)C12—H120.9300
O1—C11.347 (3)C13—H130.9300
O1—H10.8200C14—C231.506 (3)
N1—C71.477 (3)C14—C151.529 (4)
N1—C141.497 (3)C14—H140.9800
N1—H1A0.9274C15—C161.520 (5)
C1—C21.391 (3)C15—H15A0.9700
C1—C61.401 (3)C15—H15B0.9700
C2—C31.379 (3)C16—C171.488 (4)
C3—C41.372 (3)C16—H16A0.9700
C3—H30.9300C16—H16B0.9700
C4—C51.382 (4)C17—C181.506 (4)
C5—C61.394 (3)C17—H17A0.9700
C5—H50.9300C17—H17B0.9700
C6—C71.528 (3)C18—C231.390 (3)
C7—C81.516 (3)C18—C191.394 (4)
C7—H70.9800C19—C201.363 (5)
C8—C91.364 (3)C19—H190.9300
C8—C131.388 (3)C20—C211.366 (5)
C9—C101.380 (4)C20—H200.9300
C9—H90.9300C21—C221.374 (4)
C10—C111.363 (4)C21—H210.9300
C10—H100.9300C22—C231.397 (3)
C11—C121.370 (4)C22—H220.9300
C11—H110.9300
C1—O1—H1109.5C12—C13—H13119.8
C7—N1—C14115.19 (18)C8—C13—H13119.8
C7—N1—H1A107.8N1—C14—C23108.07 (19)
C14—N1—H1A112.5N1—C14—C15110.1 (2)
O1—C1—C2118.8 (2)C23—C14—C15112.1 (2)
O1—C1—C6122.2 (2)N1—C14—H14108.8
C2—C1—C6118.9 (2)C23—C14—H14108.8
C3—C2—C1122.2 (2)C15—C14—H14108.8
C3—C2—Cl1119.50 (19)C16—C15—C14111.8 (3)
C1—C2—Cl1118.28 (18)C16—C15—H15A109.2
C4—C3—C2118.2 (2)C14—C15—H15A109.2
C4—C3—H3120.9C16—C15—H15B109.2
C2—C3—H3120.9C14—C15—H15B109.2
C3—C4—C5121.6 (2)H15A—C15—H15B107.9
C3—C4—Cl2118.63 (19)C17—C16—C15110.6 (3)
C5—C4—Cl2119.8 (2)C17—C16—H16A109.5
C4—C5—C6120.3 (2)C15—C16—H16A109.5
C4—C5—H5119.8C17—C16—H16B109.5
C6—C5—H5119.8C15—C16—H16B109.5
C5—C6—C1118.9 (2)H16A—C16—H16B108.1
C5—C6—C7121.7 (2)C16—C17—C18113.5 (2)
C1—C6—C7119.1 (2)C16—C17—H17A108.9
N1—C7—C8114.22 (18)C18—C17—H17A108.9
N1—C7—C6109.03 (18)C16—C17—H17B108.9
C8—C7—C6114.74 (18)C18—C17—H17B108.9
N1—C7—H7106.0H17A—C17—H17B107.7
C8—C7—H7106.0C23—C18—C19118.6 (3)
C6—C7—H7106.0C23—C18—C17121.7 (3)
C9—C8—C13118.0 (2)C19—C18—C17119.6 (3)
C9—C8—C7120.6 (2)C20—C19—C18121.6 (3)
C13—C8—C7121.4 (2)C20—C19—H19119.2
C8—C9—C10121.7 (3)C18—C19—H19119.2
C8—C9—H9119.2C19—C20—C21120.2 (3)
C10—C9—H9119.2C19—C20—H20119.9
C11—C10—C9119.9 (3)C21—C20—H20119.9
C11—C10—H10120.1C20—C21—C22119.5 (3)
C9—C10—H10120.1C20—C21—H21120.3
C10—C11—C12119.9 (3)C22—C21—H21120.3
C10—C11—H11120.1C21—C22—C23121.5 (3)
C12—C11—H11120.1C21—C22—H22119.3
C11—C12—C13120.0 (3)C23—C22—H22119.3
C11—C12—H12120.0C18—C23—C22118.6 (2)
C13—C12—H12120.0C18—C23—C14121.9 (2)
C12—C13—C8120.5 (3)C22—C23—C14119.4 (2)
O1—C1—C2—C3179.3 (2)C9—C10—C11—C121.0 (5)
C6—C1—C2—C31.8 (4)C10—C11—C12—C130.2 (5)
O1—C1—C2—Cl11.7 (3)C11—C12—C13—C80.7 (4)
C6—C1—C2—Cl1175.70 (17)C9—C8—C13—C120.8 (4)
C1—C2—C3—C41.2 (4)C7—C8—C13—C12179.8 (2)
Cl1—C2—C3—C4176.30 (18)C7—N1—C14—C23151.31 (19)
C2—C3—C4—C50.1 (4)C7—N1—C14—C1585.9 (3)
C2—C3—C4—Cl2179.11 (18)N1—C14—C15—C1675.5 (3)
C3—C4—C5—C60.8 (4)C23—C14—C15—C1644.8 (3)
Cl2—C4—C5—C6179.76 (18)C14—C15—C16—C1761.3 (4)
C4—C5—C6—C10.1 (3)C15—C16—C17—C1847.3 (4)
C4—C5—C6—C7173.8 (2)C16—C17—C18—C2320.0 (5)
O1—C1—C6—C5178.5 (2)C16—C17—C18—C19162.2 (3)
C2—C1—C6—C51.1 (3)C23—C18—C19—C200.1 (5)
O1—C1—C6—C74.6 (3)C17—C18—C19—C20178.0 (3)
C2—C1—C6—C7172.7 (2)C18—C19—C20—C211.0 (5)
C14—N1—C7—C864.2 (3)C19—C20—C21—C220.5 (5)
C14—N1—C7—C6166.00 (18)C20—C21—C22—C230.8 (4)
C5—C6—C7—N1144.8 (2)C19—C18—C23—C221.2 (4)
C1—C6—C7—N141.6 (3)C17—C18—C23—C22176.6 (3)
C5—C6—C7—C815.2 (3)C19—C18—C23—C14177.5 (2)
C1—C6—C7—C8171.1 (2)C17—C18—C23—C144.6 (4)
N1—C7—C8—C9122.7 (2)C21—C22—C23—C181.7 (4)
C6—C7—C8—C9110.3 (3)C21—C22—C23—C14177.1 (2)
N1—C7—C8—C1357.9 (3)N1—C14—C23—C18104.4 (2)
C6—C7—C8—C1369.0 (3)C15—C14—C23—C1817.2 (3)
C13—C8—C9—C100.0 (4)N1—C14—C23—C2274.3 (3)
C7—C8—C9—C10179.4 (2)C15—C14—C23—C22164.1 (2)
C8—C9—C10—C110.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.596 (3)142
N1—H1A···Cl1i0.932.663.576 (2)171
Symmetry code: (i) x+1, y, z+1.
 

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