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The title compound, C21H16FNO3·CH3OH, was synthesized by the reaction of 1-naphthol with methyl cyano­acetate and 3-fluoro­benzaldehyde in methanol under microwave irradiation. The pyran rings of the two independent mol­ecules in the asymmetric unit adopt boat conformations. The crystal packing is stabilized by inter­molecular N—H...O, O—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000335/ci2261sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000335/ci2261Isup2.hkl
Contains datablock I

CCDC reference: 640296

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.065
  • wR factor = 0.193
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Methyl 2-amino-4-(3-fluorophenyl)-4H-benzo[h]chromene-3-carboxylate methanol solvate top
Crystal data top
C21H16FNO3·CH4OZ = 4
Mr = 381.39F(000) = 800
Triclinic, P1Dx = 1.290 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.225 (2) ÅCell parameters from 25 reflections
b = 11.375 (2) Åθ = 10–12°
c = 17.283 (4) ŵ = 0.10 mm1
α = 76.26 (3)°T = 293 K
β = 71.80 (3)°Block, colourless
γ = 71.50 (3)°0.40 × 0.30 × 0.30 mm
V = 1964.4 (8) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
4171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.3°
ω/2θ scansh = 1213
Absorption correction: ψ scan
(North et al., 1968)
k = 1314
Tmin = 0.962, Tmax = 0.972l = 021
7688 measured reflections3 standard reflections every 200 reflections
7688 independent reflections intensity decay: none
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
7688 reflections(Δ/σ)max = 0.001
506 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. 1H NMR (CDCl3): δ 7.95 (d, 1H),7.77(d, 2H), 7.43 (d, 2H), 7.29 (m, 1H), 7.09 (d, 2H), 6.99 (m, 1H), 6.75 (m, 1H), 6.30 (m, 1H), 5.60 (s, 1H), 3.73(s, 3H).

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
F10.2564 (6)0.4151 (5)0.3817 (4)0.149 (2)
O10.2548 (3)0.0661 (3)0.16499 (17)0.0652 (10)
O20.0570 (3)0.0254 (3)0.09241 (17)0.1087 (18)
O30.1881 (3)0.0810 (4)0.1963 (2)0.0651 (10)
O40.4695 (4)0.7903 (5)0.9942 (3)0.1108 (18)
H4B0.48610.71661.01570.166*
N10.1966 (4)0.0615 (5)0.0592 (3)0.0714 (13)
H1A0.27820.08670.03620.086*
H1B0.14050.04900.03170.086*
C10.0407 (2)0.3724 (4)0.2171 (3)0.106 (3)
H1C0.09640.41880.18130.128*
C20.0682 (2)0.4288 (4)0.2751 (3)0.107 (3)
H2A0.08610.51320.27860.128*
C30.1454 (3)0.3596 (4)0.3249 (3)0.091 (2)
C40.1250 (2)0.2379 (3)0.3226 (3)0.0669 (15)
H4A0.18260.19350.35840.080*
C50.0173 (2)0.1786 (2)0.2664 (3)0.0527 (12)
C60.0646 (2)0.2462 (3)0.2136 (3)0.0761 (17)
H6A0.13660.20750.17520.091*
C70.0103 (2)0.0371 (2)0.2663 (3)0.0469 (10)
H7A0.06670.01060.30170.056*
C80.0333 (2)0.0065 (2)0.1816 (3)0.0507 (11)
C90.1575 (3)0.0423 (2)0.1364 (3)0.0487 (11)
C100.2407 (3)0.0880 (2)0.2535 (3)0.0507 (11)
C110.3485 (3)0.1572 (2)0.2845 (3)0.0583 (13)
C120.4708 (4)0.2120 (2)0.2337 (3)0.0727 (16)
H12A0.48230.20040.17700.087*
C130.5734 (4)0.2827 (3)0.2674 (3)0.088 (2)
H13A0.65370.31750.23360.106*
C140.5544 (4)0.3011 (3)0.3532 (3)0.089 (2)
H14A0.62300.34820.37620.106*
C150.4384 (4)0.2513 (2)0.4026 (3)0.0820 (18)
H15A0.42790.26700.45940.098*
C160.3327 (4)0.1765 (2)0.3710 (3)0.0624 (14)
C170.2104 (3)0.1223 (2)0.4209 (4)0.0767 (16)
H17A0.19900.13340.47760.092*
C180.1108 (2)0.0555 (2)0.3893 (3)0.0626 (13)
H18A0.03200.02120.42460.075*
C190.1209 (3)0.0347 (2)0.3023 (3)0.0489 (11)
C200.0746 (2)0.0270 (2)0.1482 (3)0.0531 (12)
C210.3012 (4)0.1015 (3)0.1676 (2)0.086 (2)
H21A0.37710.14150.20620.130*
H21B0.30960.02250.16240.130*
H21C0.29250.15420.11490.130*
C220.5776 (5)0.8160 (5)0.9426 (6)0.182 (6)
H22A0.55830.90230.91730.273*
H22B0.61100.76300.90070.273*
H22C0.64140.80110.97250.273*
F20.6167 (4)0.0926 (3)0.4294 (3)0.1062 (14)
O50.1703 (3)0.6173 (3)0.2181 (2)0.0580 (9)
O60.5473 (3)0.5256 (4)0.0651 (2)0.0743 (11)
O70.6211 (3)0.4393 (3)0.1777 (2)0.0627 (10)
O81.0305 (5)0.7351 (5)0.0521 (4)0.1151 (19)
H8A1.00620.80760.06130.173*
N20.2812 (4)0.5989 (5)0.0906 (3)0.0695 (13)
H2B0.20690.63360.07980.083*
H2C0.34960.57840.05130.083*
C230.4574 (7)0.0844 (5)0.3717 (4)0.0741 (16)
H23A0.47200.00140.39060.089*
C240.5255 (4)0.1515 (3)0.3864 (4)0.0628 (14)
C250.5053 (4)0.2797 (3)0.3599 (3)0.0570 (12)
H25A0.55370.32320.37150.068*
C260.4142 (4)0.3418 (3)0.3170 (3)0.0476 (11)
C270.3439 (3)0.2736 (2)0.3012 (3)0.0583 (12)
H27A0.28140.31470.27210.070*
C280.3646 (4)0.1466 (2)0.3277 (3)0.0704 (15)
H28A0.31670.10240.31620.084*
C290.3871 (4)0.4827 (4)0.2892 (3)0.0483 (11)
H29A0.45200.51110.30160.058*
C300.3985 (4)0.5207 (4)0.1973 (3)0.0501 (11)
C310.2905 (4)0.5768 (4)0.1682 (3)0.0508 (11)
C320.1560 (3)0.6115 (4)0.3020 (3)0.0509 (11)
C330.0296 (2)0.6755 (4)0.3443 (3)0.0581 (13)
C340.0692 (2)0.7446 (5)0.3058 (4)0.0678 (15)
H34A0.05510.74850.24940.081*
C350.1865 (3)0.8066 (6)0.3508 (4)0.086 (2)
H35A0.25090.85320.32420.103*
C360.2121 (7)0.8018 (6)0.4358 (6)0.103 (3)
H36A0.29270.84390.46570.123*
C370.1189 (3)0.7357 (7)0.4733 (5)0.099 (3)
H37A0.13660.73230.53000.118*
C380.0067 (2)0.6701 (5)0.4308 (4)0.0726 (17)
C390.1084 (2)0.6014 (6)0.4686 (4)0.0822 (19)
H39A0.09350.59580.52520.099*
C400.2269 (3)0.5435 (5)0.4245 (3)0.0659 (14)
H40A0.29180.49940.45130.079*
C410.2538 (3)0.5488 (4)0.3385 (3)0.0525 (12)
C420.5226 (4)0.4960 (5)0.1404 (3)0.0518 (11)
C430.7488 (5)0.4164 (6)0.1246 (3)0.087 (2)
H43A0.81080.37640.15670.130*
H43B0.76520.49450.09410.130*
H43C0.75660.36280.08690.130*
C440.9358 (8)0.7060 (7)0.0402 (2)0.144 (4)
H44A0.96420.62100.02950.217*
H44B0.90880.76140.00610.217*
H44C0.86410.71380.08850.217*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.120 (5)0.107 (3)0.141 (5)0.042 (3)0.061 (4)0.081 (3)
O10.042 (2)0.056 (3)0.059 (2)0.0116 (18)0.0184 (17)0.0118 (18)
O20.077 (3)0.115 (5)0.080 (3)0.039 (3)0.002 (2)0.054 (3)
O30.0463 (19)0.089 (3)0.060 (2)0.0076 (18)0.0133 (16)0.0269 (19)
O40.070 (3)0.091 (3)0.119 (4)0.000 (2)0.011 (3)0.004 (3)
N10.050 (2)0.109 (4)0.056 (3)0.012 (2)0.010 (2)0.029 (2)
C10.097 (5)0.072 (4)0.180 (8)0.035 (4)0.083 (6)0.006 (5)
C20.122 (6)0.046 (3)0.188 (9)0.007 (4)0.108 (7)0.031 (5)
C30.100 (5)0.066 (4)0.120 (6)0.020 (4)0.067 (5)0.046 (4)
C40.067 (3)0.068 (3)0.066 (3)0.003 (3)0.031 (3)0.020 (3)
C50.050 (3)0.052 (3)0.063 (3)0.008 (2)0.025 (2)0.015 (2)
C60.061 (3)0.058 (3)0.113 (5)0.019 (3)0.036 (3)0.003 (3)
C70.045 (2)0.046 (2)0.047 (2)0.013 (2)0.008 (2)0.0075 (19)
C80.049 (3)0.050 (3)0.055 (3)0.017 (2)0.009 (2)0.011 (2)
C90.043 (2)0.060 (3)0.048 (3)0.012 (2)0.018 (2)0.010 (2)
C100.054 (3)0.046 (2)0.057 (3)0.016 (2)0.018 (2)0.008 (2)
C110.064 (3)0.041 (2)0.078 (4)0.016 (2)0.027 (3)0.009 (2)
C120.059 (3)0.067 (3)0.098 (4)0.008 (3)0.028 (3)0.026 (3)
C130.069 (4)0.071 (4)0.135 (6)0.002 (3)0.044 (4)0.037 (4)
C140.090 (5)0.063 (4)0.128 (6)0.006 (3)0.072 (5)0.005 (4)
C150.101 (5)0.056 (3)0.101 (5)0.017 (3)0.060 (4)0.006 (3)
C160.078 (4)0.040 (3)0.077 (4)0.015 (2)0.042 (3)0.003 (2)
C170.096 (5)0.071 (4)0.061 (3)0.020 (3)0.027 (3)0.001 (3)
C180.070 (3)0.068 (3)0.049 (3)0.017 (3)0.020 (3)0.003 (2)
C190.058 (3)0.043 (2)0.050 (3)0.019 (2)0.016 (2)0.0045 (19)
C200.048 (3)0.065 (3)0.044 (2)0.008 (2)0.010 (2)0.015 (2)
C210.047 (3)0.129 (6)0.082 (4)0.004 (3)0.020 (3)0.036 (4)
C220.089 (6)0.217 (13)0.194 (12)0.062 (7)0.005 (7)0.040 (10)
F20.107 (4)0.072 (2)0.107 (3)0.003 (2)0.070 (3)0.010 (2)
O50.0443 (18)0.068 (2)0.0507 (19)0.0036 (15)0.0076 (15)0.0115 (16)
O60.051 (2)0.104 (3)0.050 (2)0.003 (2)0.0114 (16)0.0031 (19)
O70.0445 (18)0.082 (2)0.055 (2)0.0110 (17)0.0171 (16)0.0013 (17)
O80.093 (3)0.092 (3)0.177 (6)0.004 (3)0.078 (4)0.023 (3)
N20.047 (2)0.098 (3)0.050 (2)0.002 (2)0.0152 (19)0.011 (2)
C230.097 (4)0.047 (3)0.065 (3)0.015 (3)0.010 (3)0.003 (2)
C240.074 (3)0.053 (3)0.053 (3)0.002 (3)0.025 (3)0.001 (2)
C250.067 (3)0.057 (3)0.049 (3)0.016 (2)0.020 (2)0.005 (2)
C260.050 (3)0.047 (2)0.040 (2)0.014 (2)0.002 (2)0.0060 (18)
C270.057 (3)0.052 (3)0.068 (3)0.016 (2)0.018 (3)0.010 (2)
C280.071 (4)0.059 (3)0.081 (4)0.023 (3)0.009 (3)0.017 (3)
C290.050 (3)0.051 (3)0.046 (2)0.015 (2)0.015 (2)0.0049 (19)
C300.049 (3)0.048 (2)0.049 (3)0.012 (2)0.010 (2)0.005 (2)
C310.047 (3)0.048 (3)0.053 (3)0.010 (2)0.011 (2)0.004 (2)
C320.051 (3)0.044 (2)0.058 (3)0.018 (2)0.006 (2)0.013 (2)
C330.057 (3)0.038 (2)0.070 (3)0.016 (2)0.003 (3)0.014 (2)
C340.053 (3)0.047 (3)0.089 (4)0.011 (2)0.000 (3)0.013 (3)
C350.064 (4)0.059 (3)0.107 (5)0.014 (3)0.009 (4)0.008 (3)
C360.071 (4)0.062 (4)0.128 (7)0.000 (3)0.027 (4)0.021 (4)
C370.104 (5)0.073 (4)0.085 (5)0.027 (4)0.040 (4)0.030 (4)
C380.082 (4)0.047 (3)0.070 (4)0.014 (3)0.010 (3)0.018 (3)
C390.110 (5)0.072 (4)0.055 (3)0.027 (4)0.005 (3)0.023 (3)
C400.080 (4)0.058 (3)0.056 (3)0.019 (3)0.011 (3)0.011 (2)
C410.063 (3)0.044 (2)0.052 (3)0.022 (2)0.005 (2)0.012 (2)
C420.043 (2)0.061 (3)0.048 (3)0.011 (2)0.012 (2)0.005 (2)
C430.044 (3)0.122 (6)0.078 (4)0.014 (3)0.013 (3)0.002 (4)
C440.129 (8)0.126 (8)0.202 (11)0.048 (6)0.064 (8)0.021 (7)
Geometric parameters (Å, º) top
F1—C31.395 (9)F2—C241.362 (6)
O1—C91.264 (5)O5—C311.358 (5)
O1—C101.456 (5)O5—C321.396 (6)
O2—C201.185 (5)O6—C421.227 (6)
O3—C201.333 (5)O7—C421.361 (5)
O3—C211.436 (6)O7—C431.422 (6)
O4—C221.333 (9)O8—C441.294 (10)
O4—H4B0.82O8—H8A0.82
N1—C91.318 (6)N2—C311.336 (6)
N1—H1A0.86N2—H2B0.86
N1—H1B0.86N2—H2C0.86
C1—C61.387 (9)C23—C241.348 (8)
C1—C21.398 (12)C23—C281.391 (8)
C1—H1C0.93C23—H23A0.93
C2—C31.325 (11)C24—C251.387 (7)
C2—H2A0.93C25—C261.364 (7)
C3—C41.338 (9)C25—H25A0.93
C4—C51.385 (7)C26—C271.386 (7)
C4—H4A0.93C26—C291.520 (6)
C5—C61.364 (8)C27—C281.375 (7)
C5—C71.540 (6)C27—H27A0.93
C6—H6A0.93C28—H28A0.93
C7—C191.481 (6)C29—C301.518 (6)
C7—C81.510 (6)C29—C411.524 (7)
C7—H7A0.98C29—H29A0.98
C8—C91.376 (6)C30—C311.367 (6)
C8—C201.431 (7)C30—C421.420 (6)
C10—C191.380 (7)C32—C411.354 (7)
C10—C111.404 (7)C32—C331.424 (7)
C11—C121.418 (8)C33—C341.396 (8)
C11—C161.420 (8)C33—C381.425 (8)
C12—C131.386 (8)C34—C351.367 (8)
C12—H12A0.93C34—H34A0.93
C13—C141.405 (10)C35—C361.397 (11)
C13—H13A0.93C35—H35A0.93
C14—C151.347 (10)C36—C371.331 (11)
C14—H14A0.93C36—H36A0.93
C15—C161.405 (8)C37—C381.424 (9)
C15—H15A0.93C37—H37A0.93
C16—C171.409 (8)C38—C391.413 (9)
C17—C181.331 (8)C39—C401.355 (8)
C17—H17A0.93C39—H39A0.93
C18—C191.438 (7)C40—C411.413 (7)
C18—H18A0.93C40—H40A0.93
C21—H21A0.96C43—H43A0.96
C21—H21B0.96C43—H43B0.96
C21—H21C0.96C43—H43C0.96
C22—H22A0.96C44—H44A0.96
C22—H22B0.96C44—H44B0.96
C22—H22C0.96C44—H44C0.96
C9—O1—C10120.9 (3)C31—O5—C32119.4 (4)
C20—O3—C21116.3 (4)C42—O7—C43116.0 (4)
C22—O4—H4B109.5C44—O8—H8A109.5
C9—N1—H1A120.0C31—N2—H2B120.0
C9—N1—H1B120.0C31—N2—H2C120.0
H1A—N1—H1B120.0H2B—N2—H2C120.0
C6—C1—C2119.0 (7)C24—C23—C28118.3 (5)
C6—C1—H1C120.5C24—C23—H23A120.9
C2—C1—H1C120.5C28—C23—H23A120.9
C3—C2—C1118.8 (6)C23—C24—F2119.3 (5)
C3—C2—H2A120.6C23—C24—C25122.4 (5)
C1—C2—H2A120.6F2—C24—C25118.3 (5)
C2—C3—C4123.4 (7)C26—C25—C24119.8 (5)
C2—C3—F1119.5 (7)C26—C25—H25A120.1
C4—C3—F1117.1 (8)C24—C25—H25A120.1
C3—C4—C5119.4 (7)C25—C26—C27118.3 (4)
C3—C4—H4A120.3C25—C26—C29121.1 (4)
C5—C4—H4A120.3C27—C26—C29120.5 (4)
C6—C5—C4119.2 (5)C28—C27—C26121.5 (5)
C6—C5—C7121.1 (5)C28—C27—H27A119.3
C4—C5—C7119.7 (5)C26—C27—H27A119.3
C5—C6—C1120.1 (7)C27—C28—C23119.7 (5)
C5—C6—H6A119.9C27—C28—H28A120.1
C1—C6—H6A119.9C23—C28—H28A120.1
C19—C7—C8110.9 (4)C30—C29—C26113.4 (4)
C19—C7—C5110.7 (4)C30—C29—C41110.5 (4)
C8—C7—C5112.6 (4)C26—C29—C41110.2 (4)
C19—C7—H7A107.5C30—C29—H29A107.5
C8—C7—H7A107.5C26—C29—H29A107.5
C5—C7—H7A107.5C41—C29—H29A107.5
C9—C8—C20119.6 (4)C31—C30—C42119.1 (4)
C9—C8—C7120.5 (4)C31—C30—C29121.0 (4)
C20—C8—C7119.9 (4)C42—C30—C29119.9 (4)
O1—C9—N1109.7 (4)N2—C31—O5108.7 (4)
O1—C9—C8121.6 (4)N2—C31—C30128.4 (4)
N1—C9—C8128.5 (4)O5—C31—C30122.8 (4)
C19—C10—C11123.5 (5)C41—C32—O5122.3 (4)
C19—C10—O1117.2 (4)C41—C32—C33124.2 (5)
C11—C10—O1119.3 (4)O5—C32—C33113.5 (4)
C10—C11—C12122.9 (5)C34—C33—C32124.0 (5)
C10—C11—C16118.4 (5)C34—C33—C38119.4 (5)
C12—C11—C16118.7 (5)C32—C33—C38116.6 (5)
C13—C12—C11120.9 (6)C35—C34—C33120.1 (6)
C13—C12—H12A119.6C35—C34—H34A119.9
C11—C12—H12A119.6C33—C34—H34A119.9
C14—C13—C12119.1 (6)C34—C35—C36121.7 (7)
C14—C13—H13A120.4C34—C35—H35A119.2
C12—C13—H13A120.4C36—C35—H35A119.2
C15—C14—C13120.8 (6)C37—C36—C35118.7 (6)
C15—C14—H14A119.6C37—C36—H36A120.6
C13—C14—H14A119.6C35—C36—H36A120.6
C14—C15—C16121.9 (7)C36—C37—C38123.2 (7)
C14—C15—H15A119.0C36—C37—H37A118.4
C16—C15—H15A119.0C38—C37—H37A118.4
C15—C16—C17123.3 (6)C39—C38—C37124.4 (6)
C15—C16—C11118.5 (6)C39—C38—C33118.7 (5)
C17—C16—C11118.1 (5)C37—C38—C33116.9 (7)
C18—C17—C16121.9 (5)C40—C39—C38121.7 (6)
C18—C17—H17A119.1C40—C39—H39A119.1
C16—C17—H17A119.1C38—C39—H39A119.1
C17—C18—C19122.3 (5)C39—C40—C41121.1 (6)
C17—C18—H18A118.9C39—C40—H40A119.4
C19—C18—H18A118.9C41—C40—H40A119.4
C10—C19—C18115.8 (5)C32—C41—C40117.6 (5)
C10—C19—C7121.2 (4)C32—C41—C29121.4 (4)
C18—C19—C7123.0 (4)C40—C41—C29120.9 (5)
O2—C20—O3127.6 (4)O6—C42—O7119.8 (4)
O2—C20—C8117.4 (4)O6—C42—C30127.2 (4)
O3—C20—C8113.3 (4)O7—C42—C30112.9 (4)
O3—C21—H21A109.5O7—C43—H43A109.5
O3—C21—H21B109.5O7—C43—H43B109.5
H21A—C21—H21B109.5H43A—C43—H43B109.5
O3—C21—H21C109.5O7—C43—H43C109.5
H21A—C21—H21C109.5H43A—C43—H43C109.5
H21B—C21—H21C109.5H43B—C43—H43C109.5
O4—C22—H22A109.5O8—C44—H44A109.5
O4—C22—H22B109.5O8—C44—H44B109.5
H22A—C22—H22B109.5H44A—C44—H44B109.5
O4—C22—H22C109.5O8—C44—H44C109.5
H22A—C22—H22C109.5H44A—C44—H44C109.5
H22B—C22—H22C109.5H44B—C44—H44C109.5
C6—C1—C2—C30.1 (10)C28—C23—C24—F2179.9 (5)
C1—C2—C3—C40.3 (11)C28—C23—C24—C250.7 (8)
C1—C2—C3—F1178.3 (6)C23—C24—C25—C260.5 (8)
C2—C3—C4—C50.9 (9)F2—C24—C25—C26179.7 (5)
F1—C3—C4—C5179.0 (5)C24—C25—C26—C270.1 (7)
C3—C4—C5—C61.1 (8)C24—C25—C26—C29178.3 (4)
C3—C4—C5—C7177.0 (5)C25—C26—C27—C280.1 (7)
C4—C5—C6—C10.8 (8)C29—C26—C27—C28178.3 (5)
C7—C5—C6—C1177.3 (5)C26—C27—C28—C230.4 (8)
C2—C1—C6—C50.2 (10)C24—C23—C28—C270.6 (8)
C6—C5—C7—C1972.3 (6)C25—C26—C29—C30125.8 (5)
C4—C5—C7—C19105.9 (5)C27—C26—C29—C3056.1 (6)
C6—C5—C7—C852.5 (6)C25—C26—C29—C41109.7 (5)
C4—C5—C7—C8129.4 (5)C27—C26—C29—C4168.4 (5)
C19—C7—C8—C922.0 (6)C26—C29—C30—C31107.7 (5)
C5—C7—C8—C9102.7 (5)C41—C29—C30—C3116.7 (6)
C19—C7—C8—C20157.3 (4)C26—C29—C30—C4271.3 (6)
C5—C7—C8—C2078.0 (5)C41—C29—C30—C42164.4 (4)
C10—O1—C9—N1162.1 (4)C32—O5—C31—N2176.1 (4)
C10—O1—C9—C822.9 (7)C32—O5—C31—C305.4 (7)
C20—C8—C9—O1177.3 (4)C42—C30—C31—N29.9 (8)
C7—C8—C9—O12.0 (7)C29—C30—C31—N2169.1 (5)
C20—C8—C9—N18.7 (8)C42—C30—C31—O5171.9 (4)
C7—C8—C9—N1171.9 (5)C29—C30—C31—O59.2 (7)
C9—O1—C10—C1925.4 (6)C31—O5—C32—C4110.8 (6)
C9—O1—C10—C11156.8 (4)C31—O5—C32—C33170.2 (4)
C19—C10—C11—C12179.6 (5)C41—C32—C33—C34177.1 (5)
O1—C10—C11—C122.7 (7)O5—C32—C33—C343.9 (7)
C19—C10—C11—C161.9 (7)C41—C32—C33—C380.9 (7)
O1—C10—C11—C16179.5 (4)O5—C32—C33—C38178.1 (4)
C10—C11—C12—C13178.1 (5)C32—C33—C34—C35177.8 (5)
C16—C11—C12—C130.3 (8)C38—C33—C34—C350.1 (8)
C11—C12—C13—C140.8 (9)C33—C34—C35—C360.9 (9)
C12—C13—C14—C150.2 (10)C34—C35—C36—C370.6 (10)
C13—C14—C15—C161.8 (10)C35—C36—C37—C380.5 (11)
C14—C15—C16—C17179.4 (6)C36—C37—C38—C39178.6 (7)
C14—C15—C16—C112.3 (9)C36—C37—C38—C331.2 (10)
C10—C11—C16—C15176.7 (5)C34—C33—C38—C39179.0 (5)
C12—C11—C16—C151.2 (7)C32—C33—C38—C390.9 (7)
C10—C11—C16—C171.7 (7)C34—C33—C38—C370.9 (8)
C12—C11—C16—C17179.6 (5)C32—C33—C38—C37178.9 (5)
C15—C16—C17—C18177.6 (5)C37—C38—C39—C40178.3 (6)
C11—C16—C17—C180.7 (9)C33—C38—C39—C401.5 (9)
C16—C17—C18—C190.2 (9)C38—C39—C40—C410.3 (9)
C11—C10—C19—C180.9 (7)O5—C32—C41—C40176.8 (4)
O1—C10—C19—C18178.6 (4)C33—C32—C41—C402.1 (7)
C11—C10—C19—C7179.8 (4)O5—C32—C41—C291.3 (7)
O1—C10—C19—C72.5 (6)C33—C32—C41—C29179.8 (4)
C17—C18—C19—C100.2 (7)C39—C40—C41—C321.4 (8)
C17—C18—C19—C7178.7 (5)C39—C40—C41—C29179.6 (5)
C8—C7—C19—C1018.6 (6)C30—C29—C41—C3211.6 (6)
C5—C7—C19—C10107.1 (5)C26—C29—C41—C32114.6 (5)
C8—C7—C19—C18160.2 (4)C30—C29—C41—C40170.3 (4)
C5—C7—C19—C1874.1 (6)C26—C29—C41—C4063.5 (6)
C21—O3—C20—O214.2 (8)C43—O7—C42—O61.0 (8)
C21—O3—C20—C8178.5 (5)C43—O7—C42—C30177.5 (5)
C9—C8—C20—O217.5 (7)C31—C30—C42—O64.2 (8)
C7—C8—C20—O2161.8 (4)C29—C30—C42—O6176.8 (5)
C9—C8—C20—O3176.5 (4)C31—C30—C42—O7179.6 (4)
C7—C8—C20—O34.2 (6)C29—C30—C42—O70.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···O60.862.182.754 (6)124
N1—H1B···O20.862.102.636 (5)120
N1—H1A···O4i0.862.172.993 (6)161
O4—H4B···O6ii0.822.112.929 (6)175
N1—H1B···O2iii0.862.473.263 (6)154
N2—H2B···O8iv0.862.092.945 (8)174
N2—H2C···O6v0.862.373.130 (6)148
O8—H8A···O2vi0.821.952.766 (6)175
C21—H21A···Cg1iv0.962.733.671 (4)166
C28—H28A···Cg20.932.763.616 (4)153
C43—H43A···Cg3vii0.962.763.705 (6)167
Symmetry codes: (i) x, y1, z1; (ii) x, y, z+1; (iii) x, y, z; (iv) x1, y, z; (v) x+1, y+1, z; (vi) x+1, y+1, z; (vii) x+1, y, z.
 

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