Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the structure of the title compound, C20H23FN2O2, there are two independent mol­ecules showing different conformations. The mol­ecules form centrosymmetric dimers via O—H...N or O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023032/ob6553sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023032/ob6553Isup2.hkl
Contains datablock I

CCDC reference: 282572

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.169
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N4
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C24 .. 5.19 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C32 - C33 .. 5.74 su PLAT355_ALERT_3_C Long O-H Bond (0.82A) O3 - H46 ... 1.03 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C6 - C7 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C26 - C27 ... 1.44 Ang.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 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 8 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4-[4-Dimethylamino-1-(4-fluorophenyl)-1-hydroxybutyl]-3- (hydroxymethyl)benzonitrile top
Crystal data top
C20H23FN2O2Z = 4
Mr = 342.41F(000) = 728.00
Triclinic, P1Dx = 1.214 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 8.1512 (5) ÅCell parameters from 6362 reflections
b = 12.4991 (6) Åθ = 2.2–27.4°
c = 18.928 (1) ŵ = 0.09 mm1
α = 100.708 (1)°T = 295 K
β = 96.0057 (8)°Block, colorless
γ = 94.896 (3)°0.41 × 0.28 × 0.24 mm
V = 1873.6 (2) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4412 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.023
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.947, Tmax = 0.980k = 1616
16267 measured reflectionsl = 2424
8398 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.056 w = 1/[0.0028Fo2 + σ(Fo2)]/(4Fo2)
wR(F2) = 0.169(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.39 e Å3
6842 reflectionsΔρmin = 0.41 e Å3
451 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.6611 (2)1.2782 (1)0.1972 (1)0.0893 (6)
F20.8388 (2)0.6644 (2)0.30276 (9)0.1131 (8)
O10.2838 (2)1.1075 (1)0.43657 (7)0.0479 (4)
O20.7674 (2)0.9845 (1)0.44271 (9)0.0564 (5)
O30.3860 (2)0.6202 (1)0.00455 (8)0.0568 (5)
O40.1525 (3)0.5675 (1)0.0820 (1)0.0782 (6)
N10.4866 (4)0.5378 (2)0.3791 (2)0.125 (1)
N20.0954 (3)1.2732 (2)0.4501 (1)0.0639 (7)
N30.1738 (4)1.0411 (2)0.1274 (2)0.095 (1)
N40.8642 (2)0.6249 (1)0.1262 (1)0.0638 (5)
C10.2640 (3)1.0544 (2)0.3622 (1)0.0432 (6)
C20.3164 (3)0.9386 (2)0.3629 (1)0.0437 (6)
C30.4792 (3)0.9240 (2)0.3901 (1)0.0442 (6)
C40.6148 (3)1.0175 (2)0.4180 (1)0.0531 (7)
C50.5179 (3)0.8185 (2)0.3924 (1)0.0512 (7)
C60.4024 (3)0.7282 (2)0.3689 (1)0.0581 (7)
C70.4482 (4)0.6215 (2)0.3740 (2)0.081 (1)
C80.2435 (3)0.7425 (2)0.3414 (1)0.0649 (8)
C90.2037 (3)0.8456 (2)0.3386 (1)0.0585 (7)
C100.3757 (2)1.1151 (2)0.3188 (1)0.0424 (6)
C110.4011 (3)1.0664 (2)0.2491 (1)0.0496 (6)
C120.4969 (3)1.1202 (2)0.2081 (1)0.0578 (8)
C130.5672 (3)1.2233 (2)0.2371 (1)0.0595 (8)
C140.5471 (3)1.2759 (2)0.3060 (1)0.0593 (8)
C150.4508 (3)1.2198 (2)0.3462 (1)0.0515 (7)
C160.0817 (3)1.0513 (2)0.3292 (1)0.0532 (7)
C170.0156 (3)1.1614 (2)0.3254 (1)0.0655 (8)
C180.0396 (3)1.2203 (2)0.3947 (2)0.0718 (9)
C190.1611 (5)1.3780 (3)0.4350 (2)0.100 (1)
C200.0431 (5)1.2887 (4)0.5224 (2)0.115 (2)
C210.4605 (3)0.7212 (2)0.0481 (1)0.0462 (6)
C220.3224 (3)0.7949 (2)0.0692 (1)0.0434 (6)
C230.2013 (3)0.7625 (2)0.1114 (1)0.0449 (6)
C240.1914 (3)0.6584 (2)0.1407 (1)0.0543 (7)
C250.0763 (3)0.8288 (2)0.1261 (1)0.0463 (6)
C260.0684 (3)0.9256 (2)0.1012 (1)0.0490 (6)
C270.0649 (3)0.9913 (2)0.1171 (1)0.0602 (8)
C280.1877 (3)0.9582 (2)0.0604 (1)0.0517 (7)
C290.3118 (3)0.8927 (2)0.0452 (1)0.0511 (7)
C300.5644 (3)0.7050 (2)0.1174 (1)0.0479 (6)
C310.6201 (3)0.7938 (2)0.1728 (1)0.0571 (7)
C320.7119 (3)0.7810 (3)0.2354 (1)0.0688 (9)
C330.7484 (3)0.6790 (3)0.2410 (1)0.0732 (9)
C340.6987 (3)0.5889 (3)0.1880 (2)0.0721 (9)
C350.6055 (3)0.6029 (2)0.1245 (1)0.0604 (7)
C360.5755 (3)0.7672 (2)0.0002 (1)0.0593 (7)
C370.7049 (3)0.6915 (2)0.0251 (1)0.0665 (8)
C380.7400 (4)0.6952 (2)0.0996 (1)0.0731 (9)
C391.0293 (4)0.6700 (3)0.0938 (3)0.120 (1)
C400.8525 (7)0.6089 (4)0.2044 (2)0.139 (2)
H10.57871.06640.45660.064*
H20.63221.05460.37950.065*
H30.62710.80790.41070.063*
H40.16380.68070.32430.075*
H50.09440.85540.32000.069*
H60.34920.99450.22970.060*
H70.51421.08630.16060.072*
H80.59681.34860.32460.073*
H90.43651.25350.39410.063*
H100.07031.00870.28160.063*
H110.01381.01630.35790.063*
H120.10371.20800.31450.079*
H130.07401.15050.28750.079*
H140.10171.16710.41400.088*
H150.10871.27410.38390.088*
H160.24721.36680.40510.121*
H170.20401.42590.47930.121*
H180.07491.40940.41090.121*
H190.13461.28630.55740.144*
H200.00141.35790.53300.144*
H210.04171.23240.52380.144*
H220.75640.95940.48540.070*
H230.22581.16940.44000.059*
H240.29620.65270.16600.067*
H250.10920.65920.17270.066*
H260.00740.80650.15330.056*
H270.18331.02480.04330.064*
H280.39320.91470.01680.063*
H290.59410.86430.16650.068*
H300.74980.84190.27340.080*
H310.72780.51890.19410.091*
H320.56950.54250.08600.074*
H330.63130.83550.02530.074*
H340.50990.77790.04230.074*
H350.66390.61880.02310.085*
H360.80510.71250.00690.084*
H370.63910.67340.13100.095*
H380.77790.76870.10100.095*
H391.07390.71470.12420.141*
H401.02590.71330.04710.140*
H411.09740.61290.08960.140*
H420.81290.67060.22050.178*
H430.77710.54560.22420.178*
H440.95830.59820.21970.178*
H450.15820.49890.10080.096*
H460.28990.59320.03070.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.086 (1)0.089 (1)0.114 (1)0.008 (1)0.048 (1)0.057 (1)
F20.088 (1)0.183 (2)0.072 (1)0.015 (1)0.0120 (9)0.044 (1)
O10.0550 (9)0.0497 (9)0.0411 (8)0.0098 (7)0.0078 (6)0.0118 (7)
O20.0452 (8)0.066 (1)0.064 (1)0.0038 (8)0.0065 (7)0.0301 (8)
O30.064 (1)0.0496 (9)0.0524 (9)0.0099 (8)0.0082 (7)0.0024 (7)
O40.127 (2)0.043 (1)0.070 (1)0.003 (1)0.028 (1)0.0165 (8)
N10.139 (3)0.049 (2)0.187 (4)0.017 (2)0.025 (2)0.022 (2)
N20.069 (1)0.062 (1)0.065 (1)0.018 (1)0.014 (1)0.016 (1)
N30.097 (2)0.090 (2)0.119 (2)0.046 (2)0.050 (2)0.039 (2)
N40.068 (1)0.061 (1)0.064 (1)0.017 (1)0.013 (1)0.015 (1)
C10.045 (1)0.047 (1)0.038 (1)0.000 (1)0.0053 (9)0.0105 (9)
C20.049 (1)0.044 (1)0.038 (1)0.003 (1)0.0102 (9)0.0102 (9)
C30.049 (1)0.042 (1)0.042 (1)0.001 (1)0.0126 (9)0.0108 (9)
C40.046 (1)0.049 (1)0.066 (2)0.002 (1)0.002 (1)0.022 (1)
C50.058 (1)0.044 (1)0.054 (1)0.007 (1)0.015 (1)0.011 (1)
C60.075 (2)0.041 (1)0.060 (1)0.003 (1)0.020 (1)0.009 (1)
C70.093 (2)0.044 (2)0.105 (2)0.001 (2)0.024 (2)0.011 (2)
C80.073 (2)0.044 (1)0.071 (2)0.013 (1)0.009 (1)0.003 (1)
C90.057 (1)0.052 (1)0.063 (2)0.009 (1)0.002 (1)0.011 (1)
C100.041 (1)0.043 (1)0.046 (1)0.004 (1)0.0052 (9)0.0151 (9)
C110.052 (1)0.050 (1)0.048 (1)0.004 (1)0.007 (1)0.014 (1)
C120.062 (1)0.065 (2)0.054 (1)0.013 (1)0.018 (1)0.022 (1)
C130.051 (1)0.066 (2)0.077 (2)0.016 (1)0.024 (1)0.041 (1)
C140.053 (1)0.045 (1)0.086 (2)0.007 (1)0.013 (1)0.025 (1)
C150.053 (1)0.046 (1)0.057 (1)0.004 (1)0.009 (1)0.014 (1)
C160.047 (1)0.062 (1)0.050 (1)0.001 (1)0.002 (1)0.015 (1)
C170.051 (1)0.078 (2)0.067 (2)0.009 (1)0.007 (1)0.021 (1)
C180.052 (1)0.070 (2)0.097 (2)0.010 (1)0.016 (1)0.021 (2)
C190.095 (2)0.056 (2)0.150 (3)0.010 (2)0.018 (2)0.015 (2)
C200.145 (3)0.135 (3)0.080 (2)0.067 (3)0.041 (2)0.019 (2)
C210.055 (1)0.042 (1)0.043 (1)0.010 (1)0.0124 (9)0.0060 (9)
C220.049 (1)0.039 (1)0.042 (1)0.006 (1)0.0079 (9)0.0070 (9)
C230.053 (1)0.038 (1)0.044 (1)0.004 (1)0.0094 (9)0.0071 (9)
C240.068 (1)0.045 (1)0.054 (1)0.009 (1)0.019 (1)0.013 (1)
C250.047 (1)0.044 (1)0.048 (1)0.005 (1)0.0128 (9)0.008 (1)
C260.052 (1)0.044 (1)0.052 (1)0.010 (1)0.009 (1)0.006 (1)
C270.065 (1)0.055 (1)0.068 (2)0.019 (1)0.021 (1)0.016 (1)
C280.061 (1)0.037 (1)0.061 (1)0.010 (1)0.014 (1)0.015 (1)
C290.056 (1)0.047 (1)0.056 (1)0.006 (1)0.020 (1)0.015 (1)
C300.048 (1)0.054 (1)0.045 (1)0.013 (1)0.0167 (9)0.008 (1)
C310.051 (1)0.065 (2)0.054 (1)0.002 (1)0.015 (1)0.005 (1)
C320.053 (1)0.092 (2)0.055 (2)0.002 (1)0.012 (1)0.000 (1)
C330.051 (1)0.126 (3)0.045 (1)0.010 (2)0.005 (1)0.024 (2)
C340.069 (2)0.087 (2)0.072 (2)0.029 (2)0.016 (1)0.033 (2)
C350.067 (1)0.065 (2)0.052 (1)0.020 (1)0.010 (1)0.013 (1)
C360.063 (1)0.068 (2)0.055 (1)0.018 (1)0.023 (1)0.019 (1)
C370.068 (2)0.088 (2)0.054 (1)0.029 (2)0.023 (1)0.023 (1)
C380.100 (2)0.067 (2)0.070 (2)0.036 (2)0.039 (2)0.030 (1)
C390.066 (2)0.095 (3)0.190 (4)0.010 (2)0.043 (2)0.004 (3)
C400.249 (5)0.131 (4)0.064 (2)0.094 (4)0.051 (3)0.035 (2)
Geometric parameters (Å, º) top
F1—C131.360 (3)C34—C351.400 (4)
F2—C331.366 (3)C36—C371.530 (4)
O1—C11.426 (2)C37—C381.477 (4)
O2—C41.405 (3)O1—H230.9358
O3—C211.421 (2)O2—H220.9286
O4—C241.421 (3)O3—H461.0354
N1—C71.136 (4)O4—H450.9896
N2—C181.457 (3)C4—H10.9500
N2—C191.462 (4)C4—H20.9500
N2—C201.460 (4)C5—H30.9500
N3—C271.140 (4)C8—H40.9500
N4—C381.465 (4)C9—H50.9500
N4—C391.441 (4)C11—H60.9500
N4—C401.448 (4)C12—H70.9500
C1—C21.546 (3)C14—H80.9500
C1—C101.532 (3)C15—H90.9500
C1—C161.544 (3)C16—H100.9500
C2—C31.412 (3)C16—H110.9500
C2—C91.391 (3)C17—H120.9500
C3—C41.515 (3)C17—H130.9500
C3—C51.389 (3)C18—H140.9500
C5—C61.379 (3)C18—H150.9500
C6—C71.433 (4)C19—H160.9500
C6—C81.383 (4)C19—H170.9500
C8—C91.365 (4)C19—H180.9500
C10—C111.390 (3)C20—H190.9500
C10—C151.379 (3)C20—H200.9500
C11—C121.376 (4)C20—H210.9500
C12—C131.355 (3)C24—H250.9500
C13—C141.380 (4)C24—H240.9500
C14—C151.384 (4)C25—H260.9500
C16—C171.531 (4)C28—H270.9500
C17—C161.531 (4)C29—H280.9500
C17—C181.513 (4)C31—H290.9500
C18—C171.513 (4)C32—H300.9500
C21—C221.553 (3)C34—H310.9500
C21—C301.541 (3)C35—H320.9500
C21—C361.525 (3)C36—H340.9500
C22—C231.411 (3)C36—H330.9500
C22—C291.387 (3)C37—H360.9500
C23—C241.506 (3)C37—H350.9500
C23—C251.386 (3)C38—H380.9500
C25—C261.383 (3)C38—H370.9500
C26—C271.440 (4)C39—H390.9500
C26—C281.383 (3)C39—H410.9500
C28—C291.375 (3)C39—H400.9500
C30—C311.385 (3)C40—H440.9500
C30—C351.373 (4)C40—H420.9500
C31—C321.377 (4)C40—H430.9500
C32—C331.354 (4)H12—C170.9500
C33—C341.361 (4)H13—C170.9500
F1—C13—C12119.4 (2)N2—C19—H18109.5843
F1—C13—C14118.1 (2)N2—C20—H19109.9906
F2—C33—C32119.0 (3)N2—C20—H21109.3036
F2—C33—C34117.7 (3)N2—C20—H20109.1139
O1—C1—C2104.8 (2)N4—C38—H37108.2004
O1—C1—C10111.0 (2)N4—C38—H38108.3198
O1—C1—C16109.7 (2)N4—C39—H39107.9926
O2—C4—C3114.2 (2)N4—C39—H41110.2409
O3—C21—C22109.0 (2)N4—C39—H40110.1620
O3—C21—C30112.2 (2)N4—C40—H44110.0375
O3—C21—C36103.8 (2)N4—C40—H42110.3062
O4—C24—C23109.2 (2)N4—C40—H43108.0529
N1—C7—C6178.7 (3)C1—C16—H10107.4187
N2—C18—C17114.5 (2)C1—C16—H11107.6328
C20—N2—C18111.6 (2)C2—C9—H5117.8347
C19—N2—C18110.8 (2)C3—C4—H1108.6112
C20—N2—C19110.3 (3)C3—C4—H2107.9809
N3—C27—C26177.4 (3)C3—C5—H3119.2794
N4—C38—C37115.0 (2)H2—C4—H1109.4567
C39—N4—C38111.4 (2)H3—C5—C6118.6823
C40—N4—C38110.0 (3)C6—C8—H4119.8251
C40—N4—C39110.5 (3)H4—C8—C9120.7319
C1—C2—C3120.9 (2)C8—C9—H5119.3747
C1—C2—C9121.2 (2)C10—C11—H6118.3105
C10—C1—C2110.3 (2)C10—C15—H9118.6042
C16—C1—C2112.3 (2)C11—C12—H7121.3595
C1—C10—C11120.5 (2)H6—C11—C12119.9006
C1—C10—C15121.8 (2)H7—C12—C13120.2078
C16—C1—C10108.7 (2)C13—C14—H8120.6400
C1—C16—C17117.1 (2)H8—C14—C15121.5792
C2—C3—C4123.7 (2)C14—C15—H9119.6482
C9—C2—C3117.9 (2)H10—C16—C17108.3860
C2—C3—C5118.6 (2)H11—C16—C17106.6692
C2—C9—C8122.8 (2)C16—C17—H12107.0552
C5—C3—C4117.7 (2)C16—C17—H13108.9191
C3—C5—C6122.0 (2)H11—C16—H10109.4639
C5—C6—C7119.6 (2)H12—C17—C18106.6503
C5—C6—C8119.2 (2)C17—C18—H14107.0365
C8—C6—C7121.1 (2)H13—C17—C18109.2686
C6—C8—C9119.4 (2)C17—C18—H15109.1399
C10—C11—C12121.8 (2)H13—C17—H12109.4576
C15—C10—C11117.7 (2)H15—C18—H14109.4604
C10—C15—C14121.7 (2)H17—C19—H16109.4683
C11—C12—C13118.4 (2)H18—C19—H16109.4814
C12—C13—C14122.6 (3)H18—C19—H17109.4691
C13—C14—C15117.8 (2)H21—C20—H19109.4728
C16—C17—C18115.3 (2)H20—C20—H19109.4729
C21—C22—C23120.9 (2)H21—C20—H20109.4722
C21—C22—C29120.8 (2)C21—C36—H34108.3222
C30—C21—C22109.3 (2)C21—C36—H33109.1995
C36—C21—C22113.4 (2)C22—C29—H28118.4870
C21—C30—C31120.3 (2)C23—C24—H24108.7975
C21—C30—C35120.5 (2)C23—C24—H25110.1543
C36—C21—C30109.1 (2)C23—C25—H26119.2281
C21—C36—C37113.6 (2)H24—C24—H25109.4581
C22—C23—C24125.5 (2)H26—C25—C26119.0384
C29—C22—C23118.3 (2)C26—C28—H27120.1478
C22—C23—C25118.7 (2)H27—C28—C29120.8784
C22—C29—C28122.6 (2)C28—C29—H28118.9570
C25—C23—C24115.7 (2)C30—C31—H29118.3088
C23—C25—C26121.7 (2)C30—C35—H32118.9933
C25—C26—C27119.8 (2)C31—C32—H30121.2035
C25—C26—C28119.7 (2)H29—C31—C32120.4346
C28—C26—C27120.5 (2)H30—C32—C33120.8039
C26—C28—C29119.0 (2)C33—C34—H31120.5060
C30—C31—C32121.3 (3)H31—C34—C35121.3502
C35—C30—C31119.1 (2)C34—C35—H32120.9061
C30—C35—C34120.1 (2)H34—C36—C37107.4553
C31—C32—C33118.0 (2)H33—C36—C37108.6989
C32—C33—C34123.4 (3)C36—C37—H36109.0083
C33—C34—C35118.1 (3)C36—C37—H35108.0662
C36—C37—C38112.6 (2)H33—C36—H34109.4590
H23—O1—C1107.5397H36—C37—C38108.7753
O2—C4—H1108.8113H35—C37—C38108.9046
O2—C4—H2107.7586C37—C38—H37107.8317
H22—O2—C4108.4510C37—C38—H38107.9203
H46—O3—C21106.6261H35—C37—H36109.4604
O4—C24—H24109.0070H37—C38—H38109.4620
H45—O4—C24109.1558H41—C39—H39109.4716
O4—C24—H25110.1765H40—C39—H39109.4771
N2—C18—H14107.9267H40—C39—H41109.4728
N2—C18—H15108.6452H42—C40—H44109.4672
N2—C19—H16109.6273H43—C40—H44109.4749
N2—C19—H17109.1965H43—C40—H42109.4792
C19—N2—C18—C1779.9 (3)C1—C16—C17—C1881.6 (3)
C20—N2—C18—C17156.8 (2)C16—C17—C18—N275.9 (3)
C39—N4—C38—C3774.5 (3)O3—C21—C22—C2362.5 (2)
C40—N4—C38—C37162.7 (2)O3—C21—C22—C29115.5 (2)
O1—C1—C2—C361.7 (3)C30—C21—C22—C2360.5 (2)
O1—C1—C2—C9116.5 (2)C30—C21—C22—C29121.6 (2)
C10—C1—C2—C357.9 (2)C36—C21—C22—C23177.5 (2)
C10—C1—C2—C9123.9 (2)C36—C21—C22—C290.4 (2)
C16—C1—C2—C3179.2 (2)O3—C21—C30—C31167.7 (2)
C16—C1—C2—C92.5 (3)O3—C21—C30—C3513.5 (3)
O1—C1—C10—C11167.2 (2)C22—C21—C30—C3146.7 (3)
O1—C1—C10—C1514.4 (3)C22—C21—C30—C35134.6 (2)
C2—C1—C10—C1151.4 (2)C36—C21—C30—C3177.9 (3)
C2—C1—C10—C15130.2 (2)C36—C21—C30—C35100.9 (2)
C16—C1—C10—C1172.1 (2)O3—C21—C36—C3758.2 (2)
C16—C1—C10—C15106.3 (2)C22—C21—C36—C37176.4 (2)
O1—C1—C16—C1764.0 (3)C30—C21—C36—C3761.5 (2)
C2—C1—C16—C17179.8 (2)C21—C22—C23—C240.7 (3)
C10—C1—C16—C1757.5 (3)C21—C22—C23—C25177.2 (2)
C1—C2—C3—C42.0 (3)C29—C22—C23—C24178.6 (2)
C1—C2—C3—C5177.3 (2)C29—C22—C23—C250.8 (3)
C9—C2—C3—C4179.7 (2)C21—C22—C29—C28177.5 (2)
C9—C2—C3—C51.0 (3)C23—C22—C29—C280.5 (3)
C1—C2—C9—C8176.9 (2)C22—C23—C24—O466.8 (3)
C3—C2—C9—C81.4 (4)C25—C23—C24—O4111.1 (2)
C2—C3—C4—O2179.9 (2)C22—C23—C25—C260.6 (3)
C5—C3—C4—O20.6 (3)C24—C23—C25—C26178.6 (2)
C2—C3—C5—C60.1 (3)C23—C25—C26—C27179.3 (2)
C4—C3—C5—C6179.4 (2)C23—C25—C26—C280.0 (3)
C3—C5—C6—C7178.6 (3)C25—C26—C28—C290.4 (3)
C3—C5—C6—C80.6 (4)C27—C26—C28—C29178.9 (2)
C5—C6—C8—C90.4 (4)C26—C28—C29—C220.1 (3)
C7—C6—C8—C9178.9 (2)C21—C30—C31—C32179.5 (2)
C6—C8—C9—C20.7 (4)C35—C30—C31—C321.8 (4)
C1—C10—C11—C12178.1 (2)C21—C30—C35—C34179.5 (2)
C15—C10—C11—C120.3 (3)C31—C30—C35—C341.8 (4)
C1—C10—C15—C14177.7 (2)C30—C31—C32—C330.9 (4)
C11—C10—C15—C140.7 (3)C31—C32—C33—F2179.8 (2)
C10—C11—C12—C130.2 (4)C31—C32—C33—C340.1 (4)
C11—C12—C13—F1179.4 (2)F2—C33—C34—C35179.8 (3)
C11—C12—C13—C140.4 (4)C32—C33—C34—C350.2 (4)
F1—C13—C14—C15179.8 (2)C33—C34—C35—C301.0 (4)
C12—C13—C14—C150.0 (3)C21—C36—C37—C38144.1 (2)
C13—C14—C15—C100.5 (4)C36—C37—C38—N4179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H23···N20.941.742.671 (3)172
O2—H22···O1i0.931.872.795 (2)172
O3—H46···O41.041.612.634 (3)171
O4—H45···N4ii0.991.702.686 (3)171
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds