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The title mol­ecule, C24H22O2, contains two planar naphthyl ring systems. The torsion angle around the the central C—C bond is 111.3 (2)° implying a transoid conformation with respect to the two eth­oxy substituents. Only weak inter­molecular inter­actions are present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007872/om2006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007872/om2006Isup2.hkl
Contains datablock I

CCDC reference: 605146

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.097
  • Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 6.62 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.82 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 2214 Count of symmetry unique reflns 2220 Completeness (_total/calc) 99.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PLATON.

(S)-2,2'-Diethoxy-1,1'-binaphthyl top
Crystal data top
C24H22O2Dx = 1.219 Mg m3
Mr = 342.42Melting point: 412 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4698 reflections
a = 7.5637 (5) Åθ = 1.9–26.4°
b = 11.5604 (7) ŵ = 0.08 mm1
c = 21.3353 (13) ÅT = 295 K
V = 1865.5 (2) Å3Prism, colorless
Z = 40.38 × 0.20 × 0.14 mm
F(000) = 728
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2214 independent reflections
Radiation source: fine-focus sealed tube1719 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 99
Tmin = 0.878, Tmax = 0.989k = 1413
10849 measured reflectionsl = 2622
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1176P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2214 reflectionsΔρmax = 0.13 e Å3
238 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (2)
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.4356 (0.0012) x + 2.0995 (0.0088) y - 0.5259 (0.0101) z = 1.1865 (0.0025)

* 0.0046 (0.0018) C1 * 0.0154 (0.0019) C2 * 0.0040 (0.0019) C3 * -0.0120 (0.0022) C4 * -0.0097 (0.0024) C5 * 0.0023 (0.0023) C6 * 0.0145 (0.0022) C7 * 0.0034 (0.0024) C8 * -0.0085 (0.0021) C9 * -0.0139 (0.0018) C10 - 0.0480 (0.0026) O1 - 0.2914 (0.0040) C11 - 0.5643 (0.0052) C12 - 0.0392 (0.0033) C13

Rms deviation of fitted atoms = 0.0100

- 2.8374 (0.0031) x + 0.9911 (0.0083) y + 19.6924 (0.0043) z = 1.4447 (0.0015)

Angle to previous plane (with approximate e.s.d.) = 67.92 (0.04)

* -0.0109 (0.0016) C13 * -0.0183 (0.0018) C14 * 0.0085 (0.0018) C15 * 0.0181 (0.0021) C16 * -0.0044 (0.0022) C17 * -0.0059 (0.0020) C18 * -0.0097 (0.0020) C19 * 0.0036 (0.0020) C20 * 0.0155 (0.0020) C21 * 0.0035 (0.0018) C22 - 0.0003 (0.0025) O2 0.6768 (0.0036) C23 0.9882 (0.0046) C24 0.0214 (0.0030) C1

Rms deviation of fitted atoms = 0.0113

Refinement. Friedel pairs were merged before refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1232 (2)0.10043 (13)0.02160 (7)0.0542 (4)
O20.4422 (2)0.04635 (15)0.13473 (7)0.0628 (5)
C10.1294 (3)0.13077 (17)0.08651 (9)0.0418 (5)
C20.1133 (3)0.20605 (18)0.13934 (10)0.0442 (5)
C30.1275 (3)0.1659 (2)0.20208 (10)0.0531 (6)
H30.15050.08810.20940.064*
C40.1084 (4)0.2385 (2)0.25157 (12)0.0657 (7)
H40.11770.20970.29210.079*
C50.0747 (4)0.3566 (2)0.24208 (13)0.0735 (8)
H50.06230.40590.27620.088*
C60.0604 (4)0.3983 (2)0.18325 (14)0.0697 (7)
H60.03790.47660.17740.084*
C70.0788 (3)0.32569 (19)0.13023 (12)0.0552 (6)
C80.0615 (4)0.3661 (2)0.06835 (12)0.0640 (7)
H80.03910.44420.06170.077*
C90.0763 (3)0.29544 (18)0.01820 (12)0.0569 (6)
H90.06440.32510.02210.068*
C100.1097 (3)0.17673 (18)0.02709 (10)0.0449 (5)
C110.0754 (4)0.1385 (2)0.08307 (11)0.0699 (7)
H11A0.16330.19190.09910.084*
H11B0.03800.17760.08200.084*
C120.0653 (6)0.0341 (3)0.12354 (13)0.1019 (11)
H12A0.18060.00000.12720.153*
H12B0.02340.05560.16440.153*
H12C0.01460.02090.10520.153*
C130.1598 (3)0.00437 (19)0.09562 (9)0.0427 (5)
C140.0258 (3)0.07740 (17)0.08004 (9)0.0447 (5)
C150.1413 (3)0.0444 (2)0.05567 (10)0.0515 (6)
H150.16490.03360.04890.062*
C160.2684 (4)0.1243 (2)0.04188 (11)0.0632 (7)
H160.37680.09990.02610.076*
C170.2381 (5)0.2416 (2)0.05099 (13)0.0716 (8)
H170.32470.29530.04050.086*
C180.0831 (5)0.2769 (2)0.07504 (12)0.0690 (8)
H180.06480.35550.08170.083*
C190.0539 (4)0.19761 (19)0.09059 (10)0.0541 (6)
C200.2150 (4)0.2322 (2)0.11621 (13)0.0690 (8)
H200.23520.31060.12310.083*
C210.3441 (4)0.1546 (2)0.13152 (12)0.0669 (8)
H210.44990.18020.14890.080*
C220.3164 (3)0.0350 (2)0.12089 (10)0.0523 (6)
C230.5574 (4)0.0219 (3)0.18695 (13)0.0787 (9)
H23A0.65030.03100.17420.094*
H23B0.49100.01380.22070.094*
C240.6353 (4)0.1329 (3)0.20840 (17)0.1045 (12)
H24A0.70450.16600.17520.157*
H24B0.70950.11910.24410.157*
H24C0.54230.18540.21970.157*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0689 (10)0.0558 (9)0.0380 (8)0.0021 (8)0.0019 (8)0.0086 (7)
O20.0503 (9)0.0787 (11)0.0593 (10)0.0058 (10)0.0098 (8)0.0187 (9)
C10.0420 (11)0.0417 (11)0.0419 (11)0.0012 (10)0.0005 (10)0.0057 (10)
C20.0391 (11)0.0461 (12)0.0475 (12)0.0046 (10)0.0007 (10)0.0012 (9)
C30.0526 (14)0.0607 (14)0.0460 (13)0.0017 (12)0.0025 (11)0.0011 (11)
C40.0674 (18)0.0820 (18)0.0478 (13)0.0029 (16)0.0020 (12)0.0105 (13)
C50.0778 (19)0.0720 (18)0.0706 (18)0.0048 (16)0.0021 (15)0.0262 (15)
C60.0793 (17)0.0482 (14)0.0815 (19)0.0007 (15)0.0032 (16)0.0178 (13)
C70.0523 (13)0.0462 (13)0.0670 (16)0.0023 (11)0.0023 (12)0.0016 (11)
C80.0789 (18)0.0394 (12)0.0738 (18)0.0033 (13)0.0054 (15)0.0083 (12)
C90.0640 (15)0.0504 (13)0.0562 (15)0.0017 (13)0.0064 (12)0.0160 (11)
C100.0445 (12)0.0475 (12)0.0427 (11)0.0010 (11)0.0016 (10)0.0055 (10)
C110.0831 (19)0.0834 (18)0.0432 (13)0.0114 (16)0.0111 (13)0.0100 (13)
C120.139 (3)0.111 (3)0.0560 (17)0.023 (3)0.023 (2)0.0091 (17)
C130.0485 (13)0.0453 (11)0.0343 (10)0.0066 (11)0.0048 (9)0.0059 (9)
C140.0610 (14)0.0397 (11)0.0334 (11)0.0047 (11)0.0084 (10)0.0014 (9)
C150.0607 (14)0.0449 (12)0.0488 (13)0.0049 (12)0.0003 (11)0.0015 (10)
C160.0744 (17)0.0613 (15)0.0539 (14)0.0147 (14)0.0055 (13)0.0047 (12)
C170.099 (2)0.0647 (18)0.0509 (15)0.0238 (17)0.0023 (15)0.0006 (13)
C180.117 (3)0.0384 (12)0.0516 (14)0.0101 (16)0.0171 (17)0.0013 (11)
C190.0789 (17)0.0433 (13)0.0400 (12)0.0094 (13)0.0101 (12)0.0042 (10)
C200.097 (2)0.0458 (14)0.0646 (17)0.0184 (16)0.0120 (16)0.0122 (13)
C210.0686 (17)0.0722 (18)0.0601 (16)0.0308 (16)0.0067 (13)0.0190 (14)
C220.0529 (13)0.0598 (15)0.0442 (12)0.0098 (12)0.0033 (11)0.0086 (11)
C230.0654 (16)0.108 (2)0.0628 (16)0.0114 (19)0.0185 (15)0.0162 (16)
C240.080 (2)0.137 (3)0.097 (2)0.024 (2)0.0357 (19)0.023 (2)
Geometric parameters (Å, º) top
O1—C101.367 (3)C12—H12B0.9600
O1—C111.430 (3)C12—H12C0.9600
O2—C221.370 (3)C13—C221.378 (3)
O2—C231.443 (3)C13—C141.426 (3)
C1—C101.383 (3)C14—C151.419 (3)
C1—C21.429 (3)C14—C191.424 (3)
C1—C131.492 (3)C15—C161.365 (3)
C2—C31.421 (3)C15—H150.9300
C2—C71.421 (3)C16—C171.388 (4)
C3—C41.356 (3)C16—H160.9300
C3—H30.9300C17—C181.344 (4)
C4—C51.403 (4)C17—H170.9300
C4—H40.9300C18—C191.423 (4)
C5—C61.349 (4)C18—H180.9300
C5—H50.9300C19—C201.394 (4)
C6—C71.415 (3)C20—C211.366 (4)
C6—H60.9300C20—H200.9300
C7—C81.406 (3)C21—C221.417 (4)
C8—C91.351 (3)C21—H210.9300
C8—H80.9300C23—C241.485 (4)
C9—C101.408 (3)C23—H23A0.9700
C9—H90.9300C23—H23B0.9700
C11—C121.486 (4)C24—H24A0.9600
C11—H11A0.9700C24—H24B0.9600
C11—H11B0.9700C24—H24C0.9600
C12—H12A0.9600
C10—O1—C11118.66 (18)H12B—C12—H12C109.5
C22—O2—C23116.9 (2)C22—C13—C14118.9 (2)
C10—C1—C2118.68 (18)C22—C13—C1120.4 (2)
C10—C1—C13120.83 (19)C14—C13—C1120.6 (2)
C2—C1—C13120.45 (18)C15—C14—C19117.0 (2)
C3—C2—C7117.4 (2)C15—C14—C13122.72 (19)
C3—C2—C1122.5 (2)C19—C14—C13120.3 (2)
C7—C2—C1120.03 (19)C16—C15—C14121.6 (2)
C4—C3—C2121.6 (2)C16—C15—H15119.2
C4—C3—H3119.2C14—C15—H15119.2
C2—C3—H3119.2C15—C16—C17121.0 (3)
C3—C4—C5120.6 (2)C15—C16—H16119.5
C3—C4—H4119.7C17—C16—H16119.5
C5—C4—H4119.7C18—C17—C16119.6 (3)
C6—C5—C4119.8 (2)C18—C17—H17120.2
C6—C5—H5120.1C16—C17—H17120.2
C4—C5—H5120.1C17—C18—C19121.9 (2)
C5—C6—C7121.6 (2)C17—C18—H18119.1
C5—C6—H6119.2C19—C18—H18119.1
C7—C6—H6119.2C20—C19—C18122.9 (2)
C8—C7—C6123.0 (2)C20—C19—C14118.2 (2)
C8—C7—C2118.0 (2)C18—C19—C14118.9 (3)
C6—C7—C2119.1 (2)C21—C20—C19122.0 (2)
C9—C8—C7122.3 (2)C21—C20—H20119.0
C9—C8—H8118.8C19—C20—H20119.0
C7—C8—H8118.8C20—C21—C22119.8 (3)
C8—C9—C10119.8 (2)C20—C21—H21120.1
C8—C9—H9120.1C22—C21—H21120.1
C10—C9—H9120.1O2—C22—C13117.1 (2)
O1—C10—C1116.16 (18)O2—C22—C21122.2 (2)
O1—C10—C9122.69 (19)C13—C22—C21120.8 (2)
C1—C10—C9121.1 (2)O2—C23—C24108.0 (2)
O1—C11—C12107.2 (2)O2—C23—H23A110.1
O1—C11—H11A110.3C24—C23—H23A110.1
C12—C11—H11A110.3O2—C23—H23B110.1
O1—C11—H11B110.3C24—C23—H23B110.1
C12—C11—H11B110.3H23A—C23—H23B108.4
H11A—C11—H11B108.5C23—C24—H24A109.5
C11—C12—H12A109.5C23—C24—H24B109.5
C11—C12—H12B109.5H24A—C24—H24B109.5
H12A—C12—H12B109.5C23—C24—H24C109.5
C11—C12—H12C109.5H24A—C24—H24C109.5
H12A—C12—H12C109.5H24B—C24—H24C109.5
C10—C1—C2—C3178.5 (2)C10—C1—C13—C1466.4 (3)
C13—C1—C2—C30.9 (3)C2—C1—C13—C14111.3 (2)
C10—C1—C2—C70.3 (3)C22—C13—C14—C15178.00 (19)
C13—C1—C2—C7178.0 (2)C1—C13—C14—C150.2 (3)
C7—C2—C3—C40.2 (3)C22—C13—C14—C190.1 (3)
C1—C2—C3—C4178.7 (2)C1—C13—C14—C19178.16 (19)
C2—C3—C4—C50.4 (4)C19—C14—C15—C161.1 (3)
C3—C4—C5—C60.3 (5)C13—C14—C15—C16179.1 (2)
C4—C5—C6—C70.1 (5)C14—C15—C16—C170.3 (4)
C5—C6—C7—C8178.8 (3)C15—C16—C17—C181.5 (4)
C5—C6—C7—C20.1 (4)C16—C17—C18—C191.2 (4)
C3—C2—C7—C8179.0 (2)C17—C18—C19—C20179.3 (2)
C1—C2—C7—C80.0 (3)C17—C18—C19—C140.3 (4)
C3—C2—C7—C60.0 (3)C15—C14—C19—C20178.2 (2)
C1—C2—C7—C6178.9 (2)C13—C14—C19—C200.1 (3)
C6—C7—C8—C9178.8 (3)C15—C14—C19—C181.4 (3)
C2—C7—C8—C90.1 (4)C13—C14—C19—C18179.47 (19)
C7—C8—C9—C100.2 (4)C18—C19—C20—C21179.2 (2)
C11—O1—C10—C1169.8 (2)C14—C19—C20—C210.3 (4)
C11—O1—C10—C99.7 (3)C19—C20—C21—C220.5 (4)
C2—C1—C10—O1178.86 (18)C23—O2—C22—C13148.9 (2)
C13—C1—C10—O11.2 (3)C23—O2—C22—C2131.4 (3)
C2—C1—C10—C90.6 (3)C14—C13—C22—O2179.51 (18)
C13—C1—C10—C9178.3 (2)C1—C13—C22—O22.3 (3)
C8—C9—C10—O1178.9 (2)C14—C13—C22—C210.2 (3)
C8—C9—C10—C10.6 (4)C1—C13—C22—C21178.0 (2)
C10—O1—C11—C12168.1 (2)C20—C21—C22—O2179.3 (2)
C10—C1—C13—C22115.5 (2)C20—C21—C22—C130.4 (4)
C2—C1—C13—C2266.9 (3)C22—O2—C23—C24159.7 (2)
 

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