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In the crystal structure of the title compound, C21H18FNO5, one benzene ring is almost perpendicular to the furan ring, forming a dihedral angle of 87.78 (9)°. C—H...O hydrogen bonds link the mol­ecules in the crystal structure into sheets parallel to (100).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031077/nc6046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031077/nc6046Isup2.hkl
Contains datablock I

CCDC reference: 289817

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.122
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (V1.06; Rigaku,1998); cell refinement: PROCESS-AUTO (V1.06; Rigaku,1998); data reduction: CrystalStructure (Version 3.60; Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin,1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Version 3.60; Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Dimethyl 3-(benzylamino)-2-(4-fluorophenyl)furan-4,5-dicarboxylate top
Crystal data top
C21H18FNO5F(000) = 1600.00
Mr = 383.38Dx = 1.373 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 11909 reflections
a = 19.6280 (4) Åθ = 1.9–27.5°
b = 13.1216 (3) ŵ = 0.11 mm1
c = 15.2962 (4) ÅT = 295 K
β = 109.6406 (14)°Block, colorless
V = 3710.34 (15) Å30.60 × 0.55 × 0.55 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2715 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.025
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2523
Tmin = 0.859, Tmax = 0.944k = 1717
17710 measured reflectionsl = 1919
4264 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0018Fo2 + σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max < 0.001
wR(F2) = 0.122Δρmax = 0.26 e Å3
S = 1.00Δρmin = 0.31 e Å3
4264 reflectionsExtinction correction: Larson (1970), equation 22
254 parametersExtinction coefficient: 236 (39)
H-atom parameters constrained
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
F10.11726 (6)1.00601 (8)0.16646 (8)0.0743 (3)
O10.26769 (5)0.64213 (6)0.42888 (6)0.0395 (2)
O20.13555 (6)0.37333 (9)0.47125 (9)0.0605 (3)
O30.24123 (6)0.38996 (9)0.58536 (8)0.0588 (3)
O40.40183 (6)0.57652 (9)0.54396 (9)0.0563 (3)
O50.35742 (6)0.41815 (9)0.51861 (11)0.0668 (4)
N10.08216 (6)0.58093 (9)0.39512 (9)0.0402 (3)
C10.19491 (6)0.66210 (11)0.39186 (10)0.0354 (3)
C20.15723 (6)0.58516 (11)0.41589 (9)0.0353 (3)
C30.21032 (8)0.51216 (11)0.46759 (10)0.0376 (3)
C40.27590 (8)0.55100 (11)0.47300 (10)0.0396 (4)
C50.17422 (6)0.75269 (10)0.33343 (9)0.0348 (3)
C60.22567 (8)0.82556 (12)0.33336 (11)0.0425 (4)
C70.20659 (10)0.91034 (12)0.27636 (12)0.0489 (4)
C80.13594 (10)0.92125 (12)0.22067 (11)0.0491 (4)
C90.08353 (9)0.85082 (12)0.21741 (11)0.0473 (4)
C100.10327 (8)0.76607 (12)0.27369 (10)0.0415 (4)
C110.05087 (8)0.65728 (12)0.44088 (11)0.0426 (4)
C120.06912 (6)0.64857 (12)0.54495 (11)0.0396 (3)
C130.07750 (8)0.73640 (12)0.59808 (12)0.0496 (4)
C140.08880 (10)0.73117 (16)0.69182 (12)0.0651 (6)
C150.09312 (11)0.63761 (18)0.73484 (12)0.0700 (6)
C160.08675 (10)0.55027 (16)0.68433 (12)0.0611 (5)
C170.07484 (9)0.55506 (12)0.58928 (11)0.0485 (4)
C180.19182 (9)0.41782 (12)0.50681 (10)0.0419 (4)
C190.22692 (12)0.29638 (18)0.62665 (17)0.0843 (7)
C200.35200 (8)0.51885 (12)0.51619 (11)0.0437 (4)
C210.42933 (11)0.37804 (16)0.5617 (2)0.0958 (8)
H1110.06760.72340.42820.051*
H1120.00140.65380.41290.051*
H60.27520.81680.37410.050*
H100.06730.71470.27210.050*
H90.03410.86050.17650.056*
H170.07020.49280.55350.058*
H160.09110.48470.71500.072*
H70.24250.96080.27550.059*
H130.07520.80210.56810.060*
H140.09400.79320.72790.078*
H150.10000.63400.80060.083*
H1910.19980.31180.66760.099*
H1920.27220.26390.66190.099*
H1930.19890.25080.57780.099*
H2110.45250.36990.51520.110*
H2120.42670.31250.58970.110*
H2130.45720.42500.60920.110*
H1010.06830.51190.40500.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0909 (8)0.0524 (6)0.0757 (7)0.0101 (5)0.0229 (6)0.0302 (5)
O10.0366 (5)0.0380 (5)0.0429 (5)0.0008 (4)0.0121 (4)0.0059 (4)
O20.0629 (7)0.0470 (6)0.0611 (7)0.0145 (5)0.0072 (6)0.0083 (5)
O30.0591 (7)0.0570 (7)0.0517 (7)0.0048 (5)0.0074 (5)0.0223 (5)
O40.0446 (6)0.0502 (7)0.0650 (7)0.0019 (5)0.0066 (5)0.0015 (5)
O50.0446 (6)0.0405 (6)0.1084 (11)0.0068 (5)0.0165 (6)0.0137 (6)
N10.0377 (6)0.0401 (7)0.0418 (6)0.0047 (5)0.0121 (5)0.0030 (5)
C10.0338 (7)0.0376 (7)0.0336 (7)0.0018 (5)0.0099 (5)0.0004 (5)
C20.0391 (7)0.0353 (7)0.0300 (6)0.0017 (6)0.0095 (5)0.0000 (5)
C30.0438 (8)0.0349 (7)0.0330 (7)0.0000 (6)0.0115 (6)0.0014 (5)
C40.0434 (8)0.0355 (7)0.0389 (7)0.0029 (6)0.0126 (6)0.0030 (6)
C50.0398 (7)0.0343 (7)0.0322 (7)0.0000 (6)0.0144 (5)0.0005 (5)
C60.0415 (8)0.0404 (8)0.0443 (8)0.0013 (6)0.0129 (6)0.0008 (6)
C70.0570 (9)0.0387 (8)0.0525 (9)0.0084 (7)0.0204 (7)0.0026 (7)
C80.0649 (10)0.0390 (8)0.0448 (8)0.0072 (7)0.0202 (7)0.0099 (7)
C90.0465 (8)0.0528 (9)0.0401 (8)0.0037 (7)0.0113 (6)0.0086 (7)
C100.0415 (8)0.0460 (8)0.0366 (7)0.0025 (6)0.0128 (6)0.0040 (6)
C110.0361 (7)0.0455 (8)0.0461 (8)0.0026 (6)0.0139 (6)0.0105 (7)
C120.0281 (6)0.0467 (8)0.0442 (8)0.0013 (6)0.0123 (5)0.0066 (6)
C130.0439 (8)0.0505 (9)0.0553 (9)0.0038 (7)0.0178 (7)0.0038 (8)
C140.0670 (11)0.0711 (13)0.0570 (11)0.0030 (9)0.0207 (9)0.0118 (9)
C150.0714 (12)0.0956 (16)0.0411 (9)0.0080 (11)0.0165 (8)0.0010 (10)
C160.0643 (11)0.0677 (12)0.0476 (9)0.0102 (9)0.0138 (8)0.0156 (9)
C170.0498 (9)0.0485 (9)0.0457 (9)0.0071 (7)0.0142 (7)0.0059 (7)
C180.0493 (8)0.0363 (8)0.0401 (8)0.0009 (7)0.0149 (6)0.0022 (6)
C190.0840 (15)0.0785 (14)0.0831 (14)0.0022 (11)0.0183 (11)0.0480 (12)
C200.0428 (8)0.0405 (8)0.0459 (8)0.0030 (7)0.0124 (7)0.0045 (6)
C210.0502 (11)0.0591 (13)0.164 (2)0.0181 (9)0.0179 (13)0.0285 (14)
Geometric parameters (Å, º) top
F1—C81.3618 (18)C12—C131.388 (2)
O1—C11.3734 (15)C12—C171.388 (2)
O1—C41.3558 (17)C13—C141.377 (2)
O2—C181.2053 (19)C14—C151.382 (3)
O3—C181.3170 (17)C15—C161.364 (3)
O3—C191.451 (2)C16—C171.394 (2)
O4—C201.1960 (18)N1—H1010.972
O5—C201.3251 (19)C6—H60.970
O5—C211.442 (2)C7—H70.970
N1—C21.4002 (17)C9—H90.970
N1—C111.470 (2)C10—H100.970
C1—C21.373 (2)C11—H1110.970
C1—C51.4604 (19)C11—H1120.970
C2—C31.4404 (18)C13—H130.970
C3—C41.361 (2)C14—H140.970
C3—C181.473 (2)C15—H150.970
C4—C201.477 (2)C16—H160.970
C5—C61.391 (2)C17—H170.970
C5—C101.3963 (17)C19—H1910.970
C6—C71.385 (2)C19—H1920.970
C7—C81.369 (2)C19—H1930.970
C8—C91.371 (2)C21—H2110.970
C9—C101.380 (2)C21—H2120.970
C11—C121.514 (2)C21—H2130.970
C1—O1—C4107.86 (11)O4—C20—C4124.15 (14)
C18—O3—C19116.18 (13)O5—C20—C4110.91 (12)
C20—O5—C21115.71 (12)C2—N1—H101109.3
C2—N1—C11116.19 (11)C11—N1—H101112.2
O1—C1—C2109.19 (11)C5—C6—H6119.3
O1—C1—C5116.38 (12)C7—C6—H6120.0
C2—C1—C5134.31 (11)C6—C7—H7120.8
N1—C2—C1126.09 (12)C8—C7—H7120.6
N1—C2—C3127.60 (13)C8—C9—H9120.7
C1—C2—C3106.30 (12)C10—C9—H9121.2
C2—C3—C4106.22 (12)C5—C10—H10119.1
C2—C3—C18123.40 (13)C9—C10—H10119.7
C4—C3—C18130.35 (13)N1—C11—H111106.9
O1—C4—C3110.38 (11)N1—C11—H112107.8
O1—C4—C20114.06 (13)C12—C11—H111107.5
C3—C4—C20135.55 (13)C12—C11—H112107.6
C1—C5—C6120.49 (11)H111—C11—H112109.5
C1—C5—C10120.92 (12)C12—C13—H13118.9
C6—C5—C10118.54 (12)C14—C13—H13120.1
C5—C6—C7120.65 (13)C13—C14—H14120.0
C6—C7—C8118.59 (16)C15—C14—H14119.8
F1—C8—C7118.25 (15)C14—C15—H15120.1
F1—C8—C9118.89 (14)C16—C15—H15120.0
C7—C8—C9122.86 (14)C15—C16—H16119.7
C8—C9—C10118.07 (13)C17—C16—H16120.1
C5—C10—C9121.25 (14)C12—C17—H17119.4
N1—C11—C12117.40 (12)C16—C17—H17120.1
C11—C12—C13119.51 (14)O3—C19—H191109.5
C11—C12—C17122.15 (14)O3—C19—H192109.7
C13—C12—C17118.28 (15)O3—C19—H193109.2
C12—C13—C14120.95 (16)H191—C19—H192109.5
C13—C14—C15120.18 (18)H191—C19—H193109.5
C14—C15—C16119.82 (18)H192—C19—H193109.5
C15—C16—C17120.27 (18)O5—C21—H211109.5
C12—C17—C16120.46 (16)O5—C21—H212109.7
O2—C18—O3124.01 (15)O5—C21—H213109.3
O2—C18—C3122.49 (12)H211—C21—H212109.5
O3—C18—C3113.45 (13)H211—C21—H213109.5
O4—C20—O5124.93 (13)H212—C21—H213109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O20.972.283.009 (2)132
C13—H13···O4i0.972.493.392 (2)155
C15—H15···O2ii0.972.473.430 (2)172
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y+1, z+1/2.
 

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