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The title compound, C26H25NO3, is a BINOL (1,1′-2,2′-binaphthol) derivative. In the structure, there is one intra­molecular O—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029990/fl2039sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029990/fl2039Isup2.hkl
Contains datablock I

CCDC reference: 624506

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.055
  • wR factor = 0.164
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.13 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.10 Ratio
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C25 - C26 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

N,N-Diethyl-2-(2'-hydroxy-1,1'-binaphthalen-2-yloxy)acetamide top
Crystal data top
C26H25NO3F(000) = 848
Mr = 399.47Dx = 1.269 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.361 (2) ÅCell parameters from 1603 reflections
b = 10.304 (3) Åθ = 2.6–22.3°
c = 18.355 (4) ŵ = 0.08 mm1
β = 103.242 (3)°T = 298 K
V = 2091.5 (9) Å3Block, colorless
Z = 40.42 × 0.38 × 0.21 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3688 independent reflections
Radiation source: fine-focus sealed tube1767 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1313
Tmin = 0.966, Tmax = 0.983k = 1112
10716 measured reflectionsl = 2115
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.9737P]
where P = (Fo2 + 2Fc2)/3
3688 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. 1H NMR: (300 MHz, CDCl3): δ 7.95–7.82 (m, 4H), 7.41–7.14 (m, 6H), 7.07–7.01 (m, 2H), 5.12 (d, 1H), 4.67 (d, 1H), 3.36 (q, 2H), 3.20 (q, 2H), 1.23 (t, 3H), 1.08 (t, 3H). IR (KBr, pellet): 3268, 2977, 1633, 1592, 1475, 1372, 1296, 1218, 1145, 1096, 810, 748 cm-1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.6192 (3)0.1803 (3)0.36282 (17)0.0624 (8)
O10.4943 (2)0.3032 (2)0.27688 (14)0.0648 (7)
O20.32515 (18)0.1255 (2)0.23816 (11)0.0486 (6)
O30.2741 (2)0.4257 (2)0.23628 (12)0.0553 (6)
H30.32380.38750.21800.083*
C10.5188 (3)0.1991 (3)0.30997 (19)0.0497 (9)
C20.4312 (3)0.0866 (3)0.29087 (18)0.0506 (9)
H2A0.46970.01590.27030.061*
H2B0.40970.05570.33600.061*
C30.3323 (3)0.1521 (3)0.16552 (18)0.0448 (8)
C40.4275 (3)0.1090 (3)0.1349 (2)0.0545 (9)
H40.49280.06540.16460.065*
C50.4237 (3)0.1316 (4)0.0616 (2)0.0625 (10)
H50.48680.10170.04160.075*
C60.3275 (3)0.1985 (3)0.01500 (19)0.0535 (10)
C70.3200 (4)0.2188 (4)0.0620 (2)0.0723 (12)
H70.38100.18700.08340.087*
C80.2263 (5)0.2834 (5)0.1053 (2)0.0825 (14)
H80.22220.29360.15610.099*
C90.1357 (4)0.3348 (4)0.0740 (2)0.0789 (13)
H90.07290.38180.10380.095*
C100.1384 (3)0.3170 (4)0.00036 (18)0.0586 (10)
H100.07710.35170.02030.070*
C110.2330 (3)0.2465 (3)0.04703 (18)0.0466 (9)
C120.2365 (3)0.2221 (3)0.12398 (16)0.0404 (8)
C130.1395 (3)0.2727 (3)0.15868 (16)0.0404 (8)
C140.0198 (3)0.2210 (3)0.13803 (16)0.0418 (8)
C150.0079 (3)0.1108 (3)0.09179 (17)0.0523 (9)
H150.05280.07110.07340.063*
C160.1221 (3)0.0617 (4)0.0737 (2)0.0634 (10)
H160.13820.01160.04340.076*
C170.2144 (4)0.1194 (4)0.0996 (2)0.0735 (12)
H170.29220.08510.08660.088*
C180.1921 (3)0.2252 (4)0.1439 (2)0.0680 (11)
H180.25490.26310.16100.082*
C190.0749 (3)0.2796 (3)0.16461 (19)0.0514 (9)
C200.0476 (3)0.3893 (4)0.2116 (2)0.0619 (10)
H200.10940.43160.22760.074*
C210.0670 (3)0.4337 (3)0.23369 (19)0.0567 (9)
H210.08340.50450.26580.068*
C220.1616 (3)0.3740 (3)0.20866 (17)0.0432 (8)
C230.6450 (3)0.0625 (4)0.4078 (2)0.0659 (11)
H23A0.72590.03290.40750.079*
H23B0.58870.00480.38530.079*
C240.6358 (5)0.0819 (5)0.4868 (2)0.1052 (16)
H24A0.65350.00170.51380.158*
H24B0.55540.10940.48760.158*
H24C0.69270.14700.50990.158*
C250.7079 (4)0.2855 (4)0.3814 (3)0.0853 (13)
H25A0.67490.36230.35350.102*
H25B0.71950.30550.43420.102*
C260.8224 (5)0.2585 (6)0.3663 (4)0.167 (3)
H26A0.87440.33240.37950.250*
H26B0.81260.24000.31390.250*
H26C0.85770.18470.39510.250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0575 (19)0.0445 (18)0.076 (2)0.0042 (15)0.0042 (17)0.0002 (17)
O10.0683 (16)0.0402 (15)0.0773 (18)0.0000 (13)0.0007 (13)0.0097 (13)
O20.0509 (14)0.0528 (15)0.0408 (13)0.0043 (11)0.0080 (11)0.0031 (11)
O30.0611 (15)0.0478 (14)0.0550 (15)0.0074 (12)0.0095 (12)0.0136 (12)
C10.054 (2)0.039 (2)0.053 (2)0.0072 (17)0.0073 (18)0.0012 (18)
C20.058 (2)0.042 (2)0.049 (2)0.0031 (17)0.0057 (17)0.0039 (17)
C30.056 (2)0.040 (2)0.041 (2)0.0098 (17)0.0154 (17)0.0050 (16)
C40.052 (2)0.053 (2)0.061 (2)0.0026 (18)0.0189 (18)0.0086 (19)
C50.064 (3)0.064 (3)0.070 (3)0.014 (2)0.036 (2)0.018 (2)
C60.067 (2)0.055 (2)0.045 (2)0.029 (2)0.026 (2)0.0147 (18)
C70.095 (3)0.077 (3)0.053 (3)0.041 (3)0.036 (2)0.018 (2)
C80.104 (4)0.106 (4)0.042 (2)0.059 (3)0.027 (3)0.009 (3)
C90.083 (3)0.102 (4)0.046 (2)0.037 (3)0.004 (2)0.014 (2)
C100.060 (2)0.073 (3)0.040 (2)0.024 (2)0.0075 (18)0.0045 (19)
C110.052 (2)0.049 (2)0.0368 (19)0.0236 (17)0.0073 (17)0.0077 (16)
C120.0465 (19)0.0408 (19)0.0352 (18)0.0118 (16)0.0122 (15)0.0063 (15)
C130.049 (2)0.0371 (19)0.0335 (17)0.0033 (15)0.0064 (15)0.0042 (15)
C140.046 (2)0.044 (2)0.0343 (18)0.0001 (16)0.0061 (15)0.0078 (16)
C150.056 (2)0.054 (2)0.047 (2)0.0120 (18)0.0126 (17)0.0015 (18)
C160.061 (3)0.065 (3)0.061 (2)0.019 (2)0.006 (2)0.001 (2)
C170.051 (3)0.086 (3)0.076 (3)0.011 (2)0.002 (2)0.009 (3)
C180.048 (2)0.081 (3)0.076 (3)0.009 (2)0.016 (2)0.024 (2)
C190.052 (2)0.049 (2)0.052 (2)0.0030 (18)0.0099 (18)0.0133 (18)
C200.057 (2)0.063 (3)0.067 (3)0.015 (2)0.0174 (19)0.008 (2)
C210.071 (3)0.049 (2)0.050 (2)0.008 (2)0.0131 (19)0.0032 (17)
C220.049 (2)0.040 (2)0.0380 (18)0.0002 (17)0.0035 (15)0.0025 (16)
C230.065 (2)0.056 (3)0.068 (3)0.014 (2)0.002 (2)0.002 (2)
C240.140 (4)0.099 (4)0.071 (3)0.036 (3)0.014 (3)0.000 (3)
C250.064 (3)0.065 (3)0.112 (4)0.002 (2)0.011 (3)0.006 (3)
C260.120 (5)0.167 (6)0.239 (8)0.060 (5)0.092 (5)0.072 (6)
Geometric parameters (Å, º) top
N1—C11.332 (4)C13—C221.374 (4)
N1—C231.459 (4)C13—C141.429 (4)
N1—C251.467 (5)C14—C151.409 (4)
O1—C11.232 (4)C14—C191.414 (4)
O2—C31.382 (3)C15—C161.361 (4)
O2—C21.419 (3)C15—H150.9300
O3—C221.370 (3)C16—C171.382 (5)
O3—H30.8200C16—H160.9300
C1—C21.515 (4)C17—C181.348 (5)
C2—H2A0.9700C17—H170.9300
C2—H2B0.9700C18—C191.414 (5)
C3—C121.380 (4)C18—H180.9300
C3—C41.400 (4)C19—C201.412 (5)
C4—C51.356 (5)C20—C211.352 (5)
C4—H40.9300C20—H200.9300
C5—C61.404 (5)C21—C221.403 (4)
C5—H50.9300C21—H210.9300
C6—C71.412 (5)C23—C241.490 (5)
C6—C111.425 (5)C23—H23A0.9700
C7—C81.348 (6)C23—H23B0.9700
C7—H70.9300C24—H24A0.9600
C8—C91.393 (6)C24—H24B0.9600
C8—H80.9300C24—H24C0.9600
C9—C101.370 (4)C25—C261.418 (6)
C9—H90.9300C25—H25A0.9700
C10—C111.412 (5)C25—H25B0.9700
C10—H100.9300C26—H26A0.9600
C11—C121.426 (4)C26—H26B0.9600
C12—C131.488 (4)C26—H26C0.9600
C1—N1—C23124.1 (3)C19—C14—C13120.1 (3)
C1—N1—C25119.4 (3)C16—C15—C14121.1 (3)
C23—N1—C25116.4 (3)C16—C15—H15119.5
C3—O2—C2119.0 (2)C14—C15—H15119.5
C22—O3—H3109.5C15—C16—C17120.8 (4)
O1—C1—N1123.0 (3)C15—C16—H16119.6
O1—C1—C2119.3 (3)C17—C16—H16119.6
N1—C1—C2117.7 (3)C18—C17—C16120.1 (4)
O2—C2—C1110.6 (3)C18—C17—H17119.9
O2—C2—H2A109.5C16—C17—H17119.9
C1—C2—H2A109.5C17—C18—C19121.2 (4)
O2—C2—H2B109.5C17—C18—H18119.4
C1—C2—H2B109.5C19—C18—H18119.4
H2A—C2—H2B108.1C20—C19—C18122.9 (4)
C12—C3—O2115.1 (3)C20—C19—C14118.3 (3)
C12—C3—C4121.8 (3)C18—C19—C14118.8 (3)
O2—C3—C4123.1 (3)C21—C20—C19121.0 (3)
C5—C4—C3119.5 (3)C21—C20—H20119.5
C5—C4—H4120.3C19—C20—H20119.5
C3—C4—H4120.3C20—C21—C22120.7 (3)
C4—C5—C6122.1 (3)C20—C21—H21119.6
C4—C5—H5118.9C22—C21—H21119.6
C6—C5—H5118.9O3—C22—C13123.7 (3)
C5—C6—C7122.9 (4)O3—C22—C21115.3 (3)
C5—C6—C11118.3 (3)C13—C22—C21121.0 (3)
C7—C6—C11118.9 (4)N1—C23—C24113.0 (3)
C8—C7—C6121.4 (4)N1—C23—H23A109.0
C8—C7—H7119.3C24—C23—H23A109.0
C6—C7—H7119.3N1—C23—H23B109.0
C7—C8—C9120.2 (4)C24—C23—H23B109.0
C7—C8—H8119.9H23A—C23—H23B107.8
C9—C8—H8119.9C23—C24—H24A109.5
C10—C9—C8120.6 (4)C23—C24—H24B109.5
C10—C9—H9119.7H24A—C24—H24B109.5
C8—C9—H9119.7C23—C24—H24C109.5
C9—C10—C11120.9 (4)H24A—C24—H24C109.5
C9—C10—H10119.6H24B—C24—H24C109.5
C11—C10—H10119.6C26—C25—N1114.9 (4)
C10—C11—C6118.0 (3)C26—C25—H25A108.5
C10—C11—C12122.4 (3)N1—C25—H25A108.5
C6—C11—C12119.6 (3)C26—C25—H25B108.5
C3—C12—C11118.6 (3)N1—C25—H25B108.5
C3—C12—C13120.9 (3)H25A—C25—H25B107.5
C11—C12—C13120.4 (3)C25—C26—H26A109.5
C22—C13—C14118.5 (3)C25—C26—H26B109.5
C22—C13—C12120.8 (3)H26A—C26—H26B109.5
C14—C13—C12120.6 (3)C25—C26—H26C109.5
C15—C14—C19118.0 (3)H26A—C26—H26C109.5
C15—C14—C13121.9 (3)H26B—C26—H26C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.822.172.749 (3)128
 

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