Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030369/bt6743sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030369/bt6743Isup2.hkl |
CCDC reference: 287483
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.099
- wR factor = 0.254
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.254 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C3 H7 N O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
Racemic 1,1'-bi-2-naphthol (0.29 g, 1 mmol) was dissolved in a mixed solvent system of water (5 ml) and dimethylformamide (5 ml). This solution was added to an ethanol solution (10 ml) of 2-aminopyrimidine (0.19 g, 2 mmol). Evaporation of the solvent over several weeks gave colourless block-shaped crystals of (I). The diffraction measurements represent the best of six sets of measurements; the crystals were not strongly diffracting in any of the attempts.
One DMF molecule is disordered over a twofold rotation axis. A number of restraints were imposed on this molecule, as follows: C24—O4 = 1.25 (1), C24—N2 = 1.35 (1), N2—C25 = N2—C26 = 1.45 (1), O4···C25 = 2.71 (1), C24···C25 = C24···C26 = 2.43 (2) and C25···C26 = 2.51 (2) Å. The displacement parameters of these atoms were restrained to an approximate isotropic behaviour; furthermore, these atoms were restrained to lie in a common plane. H atoms were generated geometrically (O—H = 0.82, C—Haromatic = 0.93 and C—Hmethyl = 0.96 Å), and were included in the refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C,O), or 1.5Ueq(C) for methyl groups.
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Fig. 1. A plot of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radii. |
C20H14O2·1.5C3H7NO | F(000) = 1680 |
Mr = 395.96 | Dx = 1.222 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2122 reflections |
a = 14.250 (1) Å | θ = 2.4–20.7° |
b = 10.806 (1) Å | µ = 0.08 mm−1 |
c = 28.126 (2) Å | T = 295 K |
β = 96.374 (1)° | Block, colourless |
V = 4304.1 (6) Å3 | 0.42 × 0.18 × 0.15 mm |
Z = 8 |
Bruker APEX CCD area-detector diffractometer | 3000 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω and ϕ scans | h = −16→16 |
11051 measured reflections | k = −12→8 |
3790 independent reflections | l = −33→33 |
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)] = 0.099 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.254 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.1082P)2 + 6.5323P] where P = (Fo2 + 2Fc2)/3 |
3790 reflections | (Δ/σ)max = 0.001 |
286 parameters | Δρmax = 0.46 e Å−3 |
40 restraints | Δρmin = −0.36 e Å−3 |
C20H14O2·1.5C3H7NO | V = 4304.1 (6) Å3 |
Mr = 395.96 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.250 (1) Å | µ = 0.08 mm−1 |
b = 10.806 (1) Å | T = 295 K |
c = 28.126 (2) Å | 0.42 × 0.18 × 0.15 mm |
β = 96.374 (1)° |
Bruker APEX CCD area-detector diffractometer | 3000 reflections with I > 2σ(I) |
11051 measured reflections | Rint = 0.029 |
3790 independent reflections |
R[F2 > 2σ(F2)] = 0.099 | 40 restraints |
wR(F2) = 0.254 | H-atom parameters constrained |
S = 1.18 | Δρmax = 0.46 e Å−3 |
3790 reflections | Δρmin = −0.36 e Å−3 |
286 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.5386 (2) | 0.6903 (3) | 0.5587 (1) | 0.070 (1) | |
O2 | 0.4730 (2) | 0.7629 (2) | 0.6736 (1) | 0.058 (1) | |
O3 | 0.5401 (3) | 0.8198 (5) | 0.4778 (1) | 0.118 (2) | |
O4 | 0.5000 | 0.9273 (4) | 0.7500 | 0.106 (2) | |
N1 | 0.6382 (3) | 0.9121 (4) | 0.4317 (1) | 0.065 (1) | |
N2 | 0.5000 | 1.1334 (5) | 0.7500 | 0.082 (2) | |
C1 | 0.4445 (2) | 0.5759 (3) | 0.6056 (1) | 0.036 (1) | |
C2 | 0.4549 (3) | 0.6346 (4) | 0.5632 (1) | 0.049 (1) | |
C3 | 0.3801 (3) | 0.6374 (4) | 0.5258 (1) | 0.063 (1) | |
C4 | 0.2973 (3) | 0.5809 (4) | 0.5310 (1) | 0.059 (1) | |
C5 | 0.2825 (2) | 0.5184 (3) | 0.5734 (1) | 0.046 (1) | |
C6 | 0.3570 (2) | 0.5168 (3) | 0.6114 (1) | 0.037 (1) | |
C7 | 0.3406 (3) | 0.4560 (4) | 0.6539 (1) | 0.049 (1) | |
C8 | 0.2563 (3) | 0.3997 (4) | 0.6586 (2) | 0.069 (1) | |
C9 | 0.1839 (3) | 0.4008 (4) | 0.6211 (2) | 0.068 (1) | |
C10 | 0.1968 (3) | 0.4591 (4) | 0.5798 (2) | 0.059 (1) | |
C11 | 0.5235 (2) | 0.5726 (3) | 0.6449 (1) | 0.036 (1) | |
C12 | 0.5351 (2) | 0.6656 (3) | 0.6780 (1) | 0.040 (1) | |
C13 | 0.6088 (3) | 0.6625 (4) | 0.7159 (1) | 0.053 (1) | |
C14 | 0.6715 (3) | 0.5681 (4) | 0.7196 (1) | 0.055 (1) | |
C15 | 0.6643 (3) | 0.4705 (4) | 0.6864 (1) | 0.050 (1) | |
C16 | 0.5887 (2) | 0.4722 (3) | 0.6487 (1) | 0.042 (1) | |
C17 | 0.5815 (3) | 0.3738 (4) | 0.6154 (2) | 0.057 (1) | |
C18 | 0.6466 (4) | 0.2800 (5) | 0.6193 (2) | 0.087 (2) | |
C19 | 0.7197 (4) | 0.2781 (6) | 0.6557 (2) | 0.099 (2) | |
C20 | 0.7289 (3) | 0.3714 (5) | 0.6883 (2) | 0.079 (2) | |
C21 | 0.6120 (5) | 0.8212 (6) | 0.4580 (2) | 0.100 (2) | |
C22 | 0.5824 (5) | 1.0214 (7) | 0.4251 (3) | 0.126 (3) | |
C23 | 0.7238 (6) | 0.9074 (8) | 0.4094 (3) | 0.147 (3) | |
C24 | 0.4962 (5) | 1.0288 (7) | 0.7700 (3) | 0.094 (3) | 0.50 |
C25 | 0.510 (1) | 1.125 (1) | 0.6967 (3) | 0.180 (7) | 0.50 |
C26 | 0.4978 (6) | 1.2613 (8) | 0.7627 (5) | 0.129 (6) | 0.50 |
H1 | 0.5363 | 0.7239 | 0.5325 | 0.084* | |
H2 | 0.4854 | 0.8108 | 0.6961 | 0.069* | |
H3 | 0.3879 | 0.6784 | 0.4975 | 0.076* | |
H4 | 0.2488 | 0.5835 | 0.5060 | 0.071* | |
H7 | 0.3882 | 0.4541 | 0.6793 | 0.059* | |
H8 | 0.2472 | 0.3603 | 0.6872 | 0.083* | |
H9 | 0.1269 | 0.3616 | 0.6244 | 0.081* | |
H10 | 0.1478 | 0.4602 | 0.5550 | 0.071* | |
H13 | 0.6143 | 0.7257 | 0.7385 | 0.063* | |
H14 | 0.7202 | 0.5678 | 0.7445 | 0.066* | |
H17 | 0.5323 | 0.3726 | 0.5908 | 0.069* | |
H18 | 0.6413 | 0.2164 | 0.5969 | 0.104* | |
H19 | 0.7628 | 0.2131 | 0.6580 | 0.119* | |
H20 | 0.7790 | 0.3698 | 0.7125 | 0.095* | |
H21 | 0.6513 | 0.7524 | 0.4619 | 0.120* | |
H22a | 0.5320 | 1.0081 | 0.4000 | 0.189* | |
H22b | 0.6211 | 1.0888 | 0.4166 | 0.189* | |
H22c | 0.5565 | 1.0410 | 0.4543 | 0.189* | |
H23a | 0.7629 | 0.8415 | 0.4232 | 0.220* | |
H23b | 0.7568 | 0.9846 | 0.4143 | 0.220* | |
H23c | 0.7090 | 0.8931 | 0.3757 | 0.220* | |
H24 | 0.4899 | 1.0282 | 0.8026 | 0.113* | 0.50 |
H25a | 0.5570 | 1.0645 | 0.6915 | 0.269* | 0.50 |
H25b | 0.5273 | 1.2038 | 0.6852 | 0.269* | 0.50 |
H25c | 0.4502 | 1.0998 | 0.6799 | 0.269* | 0.50 |
H26a | 0.4420 | 1.2990 | 0.7467 | 0.194* | 0.50 |
H26b | 0.5527 | 1.3021 | 0.7534 | 0.194* | 0.50 |
H26c | 0.4971 | 1.2687 | 0.7967 | 0.194* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.061 (2) | 0.097 (2) | 0.051 (2) | −0.031 (2) | 0.0004 (1) | 0.022 (2) |
O2 | 0.066 (2) | 0.046 (2) | 0.058 (2) | 0.010 (1) | −0.009 (1) | −0.013 (1) |
O3 | 0.111 (3) | 0.169 (5) | 0.072 (2) | −0.066 (3) | 0.009 (2) | 0.033 (3) |
O4 | 0.173 (5) | 0.043 (3) | 0.093 (4) | 0.000 | −0.022 (3) | 0.000 |
N1 | 0.066 (2) | 0.069 (3) | 0.061 (2) | −0.005 (2) | 0.015 (2) | 0.010 (2) |
N2 | 0.106 (4) | 0.041 (3) | 0.100 (4) | 0.000 | 0.021 (3) | 0.000 |
C1 | 0.039 (2) | 0.031 (2) | 0.037 (2) | −0.001 (1) | 0.000 (1) | −0.003 (1) |
C2 | 0.047 (2) | 0.053 (2) | 0.044 (2) | −0.008 (2) | 0.003 (2) | 0.003 (2) |
C3 | 0.068 (3) | 0.083 (3) | 0.036 (2) | −0.007 (2) | −0.008 (2) | 0.009 (2) |
C4 | 0.048 (2) | 0.075 (3) | 0.048 (2) | −0.004 (2) | −0.016 (2) | −0.002 (2) |
C5 | 0.040 (2) | 0.046 (2) | 0.049 (2) | 0.002 (2) | −0.004 (2) | −0.010 (2) |
C6 | 0.037 (2) | 0.030 (2) | 0.044 (2) | 0.002 (1) | 0.003 (2) | −0.006 (1) |
C7 | 0.043 (2) | 0.048 (2) | 0.055 (2) | −0.009 (2) | 0.002 (2) | 0.005 (2) |
C8 | 0.071 (3) | 0.066 (3) | 0.073 (3) | −0.021 (2) | 0.017 (2) | 0.006 (2) |
C9 | 0.043 (2) | 0.072 (3) | 0.089 (3) | −0.021 (2) | 0.011 (2) | −0.007 (3) |
C10 | 0.038 (2) | 0.062 (3) | 0.074 (3) | −0.008 (2) | −0.008 (2) | −0.018 (2) |
C11 | 0.035 (2) | 0.038 (2) | 0.034 (2) | −0.005 (1) | 0.004 (1) | 0.003 (1) |
C12 | 0.038 (2) | 0.037 (2) | 0.045 (2) | −0.004 (2) | 0.002 (2) | 0.006 (2) |
C13 | 0.052 (2) | 0.059 (3) | 0.044 (2) | −0.013 (2) | −0.005 (2) | −0.004 (2) |
C14 | 0.041 (2) | 0.074 (3) | 0.045 (2) | −0.001 (2) | −0.012 (2) | 0.013 (2) |
C15 | 0.041 (2) | 0.059 (2) | 0.048 (2) | 0.007 (2) | −0.001 (2) | 0.015 (2) |
C16 | 0.040 (2) | 0.041 (2) | 0.044 (2) | 0.002 (2) | 0.006 (2) | 0.008 (2) |
C17 | 0.062 (3) | 0.051 (2) | 0.059 (2) | 0.009 (2) | 0.004 (2) | −0.003 (2) |
C18 | 0.107 (4) | 0.065 (3) | 0.087 (4) | 0.035 (3) | 0.011 (3) | −0.006 (3) |
C19 | 0.106 (4) | 0.085 (4) | 0.106 (5) | 0.060 (3) | 0.006 (4) | 0.010 (3) |
C20 | 0.064 (3) | 0.097 (4) | 0.072 (3) | 0.031 (3) | −0.004 (2) | 0.020 (3) |
C21 | 0.127 (5) | 0.091 (4) | 0.077 (4) | −0.021 (4) | −0.005 (4) | 0.005 (3) |
C22 | 0.112 (5) | 0.141 (6) | 0.121 (6) | 0.032 (5) | −0.002 (4) | 0.040 (5) |
C23 | 0.127 (6) | 0.166 (8) | 0.161 (7) | −0.002 (5) | 0.079 (6) | −0.026 (6) |
C24 | 0.142 (8) | 0.079 (6) | 0.060 (5) | −0.005 (6) | 0.008 (6) | −0.017 (5) |
C25 | 0.22 (1) | 0.16 (1) | 0.16 (1) | −0.010 (9) | 0.037 (9) | 0.011 (9) |
C26 | 0.181 (9) | 0.088 (7) | 0.12 (1) | −0.005 (8) | 0.032 (8) | −0.003 (6) |
O1—C2 | 1.355 (4) | C18—C19 | 1.378 (8) |
O2—C12 | 1.371 (4) | C19—C20 | 1.360 (8) |
O3—C21 | 1.220 (7) | O1—H1 | 0.82 |
O4—C24 | 1.236 (7) | O2—H2 | 0.82 |
N1—C21 | 1.308 (7) | C3—H3 | 0.93 |
N1—C22 | 1.424 (7) | C4—H4 | 0.93 |
N1—C23 | 1.434 (7) | C7—H7 | 0.93 |
N2—C24 | 1.267 (7) | C8—H8 | 0.93 |
N2—C26 | 1.429 (8) | C9—H9 | 0.93 |
N2—C25 | 1.522 (9) | C10—H10 | 0.93 |
C1—C2 | 1.374 (5) | C13—H13 | 0.93 |
C1—C6 | 1.426 (5) | C14—H14 | 0.93 |
C1—C11 | 1.487 (4) | C17—H17 | 0.93 |
C2—C3 | 1.412 (5) | C18—H18 | 0.93 |
C3—C4 | 1.351 (6) | C19—H19 | 0.93 |
C4—C5 | 1.405 (6) | C20—H20 | 0.93 |
C5—C10 | 1.409 (5) | C21—H21 | 0.93 |
C5—C6 | 1.420 (5) | C22—H22a | 0.96 |
C6—C7 | 1.407 (5) | C22—H22b | 0.96 |
C7—C8 | 1.367 (5) | C22—H22c | 0.96 |
C8—C9 | 1.392 (7) | C23—H23a | 0.96 |
C9—C10 | 1.352 (6) | C23—H23b | 0.96 |
C11—C12 | 1.368 (5) | C23—H23c | 0.96 |
C11—C16 | 1.424 (5) | C24—H24 | 0.93 |
C12—C13 | 1.412 (5) | C25—H25a | 0.96 |
C13—C14 | 1.352 (6) | C25—H25b | 0.96 |
C14—C15 | 1.405 (6) | C25—H25c | 0.96 |
C15—C20 | 1.410 (6) | C26—H26a | 0.96 |
C15—C16 | 1.425 (5) | C26—H26b | 0.96 |
C16—C17 | 1.413 (5) | C26—H26c | 0.96 |
C17—C18 | 1.370 (6) | ||
C21—N1—C22 | 120.4 (5) | C4—C3—H3 | 119.8 |
C21—N1—C23 | 122.0 (6) | C2—C3—H3 | 119.8 |
C22—N1—C23 | 117.5 (6) | C3—C4—H4 | 119.2 |
C24—N2—C26 | 138.5 (7) | C5—C4—H4 | 119.2 |
C24—N2—C25 | 113.2 (7) | C8—C7—H7 | 119.3 |
C26—N2—C25 | 108.3 (8) | C6—C7—H7 | 119.3 |
C2—C1—C6 | 119.0 (3) | C7—C8—H8 | 119.7 |
C2—C1—C11 | 120.6 (3) | C9—C8—H8 | 119.7 |
C6—C1—C11 | 120.4 (3) | C10—C9—H9 | 120.1 |
O1—C2—C1 | 117.9 (3) | C8—C9—H9 | 120.1 |
O1—C2—C3 | 121.3 (3) | C9—C10—H10 | 119.2 |
C1—C2—C3 | 120.8 (3) | C5—C10—H10 | 119.2 |
C4—C3—C2 | 120.4 (4) | C14—C13—H13 | 119.8 |
C10—C5—C4 | 122.8 (3) | C12—C13—H13 | 119.8 |
C10—C5—C6 | 118.9 (4) | C13—C14—H14 | 119.4 |
C4—C5—C6 | 118.3 (3) | C15—C14—H14 | 119.4 |
C7—C6—C5 | 117.7 (3) | C18—C17—H17 | 119.8 |
C7—C6—C1 | 122.3 (3) | C16—C17—H17 | 119.8 |
C5—C6—C1 | 119.9 (3) | C19—C18—H18 | 119.3 |
C8—C7—C6 | 121.4 (4) | C17—C18—H18 | 119.3 |
C3—C4—C5 | 121.6 (3) | C20—C19—H19 | 120.1 |
C7—C8—C9 | 120.5 (4) | C18—C19—H19 | 120.1 |
C10—C9—C8 | 119.7 (4) | C19—C20—H20 | 119.2 |
C9—C10—C5 | 121.7 (4) | C15—C20—H20 | 119.2 |
C12—C11—C16 | 118.7 (3) | O3—C21—H21 | 117.5 |
C12—C11—C1 | 120.8 (3) | N1—C21—H21 | 117.5 |
C16—C11—C1 | 120.5 (3) | N1—C22—H22a | 109.5 |
C11—C12—O2 | 118.4 (3) | N1—C22—H22b | 109.5 |
C11—C12—C13 | 121.3 (3) | H22a—C22—H22b | 109.5 |
O2—C12—C13 | 120.3 (3) | N1—C22—H22c | 109.5 |
C14—C13—C12 | 120.4 (4) | H22a—C22—H22c | 109.5 |
C13—C14—C15 | 121.1 (3) | H22b—C22—H22c | 109.5 |
C14—C15—C20 | 123.1 (4) | N1—C23—H23a | 109.5 |
C14—C15—C16 | 118.6 (3) | N1—C23—H23b | 109.5 |
C20—C15—C16 | 118.3 (4) | H23a—C23—H23b | 109.5 |
C17—C16—C15 | 118.4 (3) | N1—C23—H23c | 109.5 |
C17—C16—C11 | 121.7 (3) | H23a—C23—H23c | 109.5 |
C15—C16—C11 | 119.9 (3) | H23b—C23—H23c | 109.5 |
C18—C17—C16 | 120.4 (4) | O4—C24—H24 | 117.2 |
C19—C18—C17 | 121.3 (5) | N2—C24—H24 | 117.2 |
C20—C19—C18 | 119.9 (5) | N2—C26—H26a | 109.5 |
C19—C20—C15 | 121.6 (5) | N2—C26—H26b | 109.5 |
O3—C21—N1 | 125.0 (7) | H26a—C26—H26b | 109.5 |
O4—C24—N2 | 125.7 (7) | N2—C26—H26c | 109.5 |
C2—O1—H1 | 109.5 | H26a—C26—H26c | 109.5 |
C12—O2—H2 | 109.5 | H26b—C26—H26c | 109.5 |
C6—C1—C2—O1 | 179.8 (3) | C16—C11—C12—O2 | 179.0 (3) |
C11—C1—C2—O1 | −0.9 (5) | C1—C11—C12—O2 | −1.1 (5) |
C6—C1—C2—C3 | 0.4 (6) | C16—C11—C12—C13 | −1.1 (5) |
C11—C1—C2—C3 | 179.7 (4) | C1—C11—C12—C13 | 178.8 (3) |
O1—C2—C3—C4 | 179.8 (4) | C11—C12—C13—C14 | 1.7 (5) |
C1—C2—C3—C4 | −0.8 (7) | O2—C12—C13—C14 | −178.4 (3) |
C2—C3—C4—C5 | 0.2 (7) | C12—C13—C14—C15 | −0.9 (6) |
C3—C4—C5—C10 | 179.7 (4) | C13—C14—C15—C20 | 178.8 (4) |
C3—C4—C5—C6 | 0.8 (6) | C13—C14—C15—C16 | −0.5 (6) |
C10—C5—C6—C7 | −0.2 (5) | C14—C15—C16—C17 | −179.9 (4) |
C4—C5—C6—C7 | 178.7 (3) | C20—C15—C16—C17 | 0.8 (5) |
C10—C5—C6—C1 | 179.8 (3) | C14—C15—C16—C11 | 1.0 (5) |
C4—C5—C6—C1 | −1.2 (5) | C20—C15—C16—C11 | −178.3 (4) |
C2—C1—C6—C7 | −179.3 (3) | C12—C11—C16—C17 | −179.3 (3) |
C11—C1—C6—C7 | 1.3 (5) | C1—C11—C16—C17 | 0.8 (5) |
C2—C1—C6—C5 | 0.6 (5) | C12—C11—C16—C15 | −0.3 (5) |
C11—C1—C6—C5 | −178.7 (3) | C1—C11—C16—C15 | 179.8 (3) |
C5—C6—C7—C8 | 0.3 (6) | C15—C16—C17—C18 | −0.7 (6) |
C1—C6—C7—C8 | −179.8 (4) | C11—C16—C17—C18 | 178.3 (4) |
C6—C7—C8—C9 | 0.2 (7) | C16—C17—C18—C19 | 0.7 (8) |
C7—C8—C9—C10 | −0.6 (7) | C17—C18—C19—C20 | −0.8 (9) |
C8—C9—C10—C5 | 0.7 (7) | C18—C19—C20—C15 | 0.9 (9) |
C4—C5—C10—C9 | −179.2 (4) | C14—C15—C20—C19 | 179.8 (5) |
C6—C5—C10—C9 | −0.2 (6) | C16—C15—C20—C19 | −0.9 (7) |
C2—C1—C11—C12 | 88.1 (4) | C22—N1—C21—O3 | 1.4 (9) |
C6—C1—C11—C12 | −92.6 (4) | C23—N1—C21—O3 | −179.9 (6) |
C2—C1—C11—C16 | −92.0 (4) | C26—N2—C24—O4 | −179.8 (5) |
C6—C1—C11—C16 | 87.3 (4) | C25—N2—C24—O4 | 0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.86 | 2.674 (5) | 172 |
O2—H2···O4 | 0.82 | 1.96 | 2.781 (4) | 174 |
Experimental details
Crystal data | |
Chemical formula | C20H14O2·1.5C3H7NO |
Mr | 395.96 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 14.250 (1), 10.806 (1), 28.126 (2) |
β (°) | 96.374 (1) |
V (Å3) | 4304.1 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.42 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11051, 3790, 3000 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.099, 0.254, 1.18 |
No. of reflections | 3790 |
No. of parameters | 286 |
No. of restraints | 40 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.36 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.86 | 2.674 (5) | 172 |
O2—H2···O4 | 0.82 | 1.96 | 2.781 (4) | 174 |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
A number of solvates and clathrates of 1,1'-bi-2-naphthol have been structurally verified, as noted from a search of the Cambridge Structural Database (Version 5.26; Allen, 2002). The reagent itself exists in the racemic and optically active (+) and (-) forms. The title 1.5DMF solvate, (I), was originally reported in space group Cc (Hirano et al., 2003), but PLATON (Spek, 2003) suggests a centre of inversion in the crystal structure; this is confirmed in the present re-investigation of (I) (Fig. 1). In the higher-symmetric space group C2/c, one of the two DMF solvates is disordered over a twofold rotation axis.
The two aromatic systems of (I) enclose a dihedral angle of 88.4 (1)°. One of the hydroxy groups forms a hydrogen bond to the ordered DMF (which lies on a general position) and the other to the disordered DMF (which lies on a twofold rotation axis). Apart from these two hydrogen bonds (Table 1), there are no other important intermolecular interactions in the crystal. Racemic 1,1'-bi-2-naphthol crystallizes in the non-centrosymmetric space group Iba2 (Gridunova et al., 1982; Mori et al., 1993; Toda et al., 1997, Nieger, 1999) and also has the two naphthol residues in an almost perpendicular orientation.