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In the crystal structure of the title compound, C
21H
18FNO
5, 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
CCDC reference: 289817
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C21H18FNO5 | F(000) = 1600.00 |
Mr = 383.38 | Dx = 1.373 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 11909 reflections |
a = 19.6280 (4) Å | θ = 1.9–27.5° |
b = 13.1216 (3) Å | µ = 0.11 mm−1 |
c = 15.2962 (4) Å | T = 295 K |
β = 109.6406 (14)° | Block, colorless |
V = 3710.34 (15) Å3 | 0.60 × 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-1 | Rint = 0.025 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −25→23 |
Tmin = 0.859, Tmax = 0.944 | k = −17→17 |
17710 measured reflections | l = −19→19 |
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) = 0.122 | Δρmax = 0.26 e Å−3 |
S = 1.00 | Δρmin = −0.31 e Å−3 |
4264 reflections | Extinction correction: Larson (1970), equation 22 |
254 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
F1 | 0.11726 (6) | 1.00601 (8) | 0.16646 (8) | 0.0743 (3) | |
O1 | 0.26769 (5) | 0.64213 (6) | 0.42888 (6) | 0.0395 (2) | |
O2 | 0.13555 (6) | 0.37333 (9) | 0.47125 (9) | 0.0605 (3) | |
O3 | 0.24123 (6) | 0.38996 (9) | 0.58536 (8) | 0.0588 (3) | |
O4 | 0.40183 (6) | 0.57652 (9) | 0.54396 (9) | 0.0563 (3) | |
O5 | 0.35742 (6) | 0.41815 (9) | 0.51861 (11) | 0.0668 (4) | |
N1 | 0.08216 (6) | 0.58093 (9) | 0.39512 (9) | 0.0402 (3) | |
C1 | 0.19491 (6) | 0.66210 (11) | 0.39186 (10) | 0.0354 (3) | |
C2 | 0.15723 (6) | 0.58516 (11) | 0.41589 (9) | 0.0353 (3) | |
C3 | 0.21032 (8) | 0.51216 (11) | 0.46759 (10) | 0.0376 (3) | |
C4 | 0.27590 (8) | 0.55100 (11) | 0.47300 (10) | 0.0396 (4) | |
C5 | 0.17422 (6) | 0.75269 (10) | 0.33343 (9) | 0.0348 (3) | |
C6 | 0.22567 (8) | 0.82556 (12) | 0.33336 (11) | 0.0425 (4) | |
C7 | 0.20659 (10) | 0.91034 (12) | 0.27636 (12) | 0.0489 (4) | |
C8 | 0.13594 (10) | 0.92125 (12) | 0.22067 (11) | 0.0491 (4) | |
C9 | 0.08353 (9) | 0.85082 (12) | 0.21741 (11) | 0.0473 (4) | |
C10 | 0.10327 (8) | 0.76607 (12) | 0.27369 (10) | 0.0415 (4) | |
C11 | 0.05087 (8) | 0.65728 (12) | 0.44088 (11) | 0.0426 (4) | |
C12 | 0.06912 (6) | 0.64857 (12) | 0.54495 (11) | 0.0396 (3) | |
C13 | 0.07750 (8) | 0.73640 (12) | 0.59808 (12) | 0.0496 (4) | |
C14 | 0.08880 (10) | 0.73117 (16) | 0.69182 (12) | 0.0651 (6) | |
C15 | 0.09312 (11) | 0.63761 (18) | 0.73484 (12) | 0.0700 (6) | |
C16 | 0.08675 (10) | 0.55027 (16) | 0.68433 (12) | 0.0611 (5) | |
C17 | 0.07484 (9) | 0.55506 (12) | 0.58928 (11) | 0.0485 (4) | |
C18 | 0.19182 (9) | 0.41782 (12) | 0.50681 (10) | 0.0419 (4) | |
C19 | 0.22692 (12) | 0.29638 (18) | 0.62665 (17) | 0.0843 (7) | |
C20 | 0.35200 (8) | 0.51885 (12) | 0.51619 (11) | 0.0437 (4) | |
C21 | 0.42933 (11) | 0.37804 (16) | 0.5617 (2) | 0.0958 (8) | |
H111 | 0.0676 | 0.7234 | 0.4282 | 0.051* | |
H112 | −0.0014 | 0.6538 | 0.4129 | 0.051* | |
H6 | 0.2752 | 0.8168 | 0.3741 | 0.050* | |
H10 | 0.0673 | 0.7147 | 0.2721 | 0.050* | |
H9 | 0.0341 | 0.8605 | 0.1765 | 0.056* | |
H17 | 0.0702 | 0.4928 | 0.5535 | 0.058* | |
H16 | 0.0911 | 0.4847 | 0.7150 | 0.072* | |
H7 | 0.2425 | 0.9608 | 0.2755 | 0.059* | |
H13 | 0.0752 | 0.8021 | 0.5681 | 0.060* | |
H14 | 0.0940 | 0.7932 | 0.7279 | 0.078* | |
H15 | 0.1000 | 0.6340 | 0.8006 | 0.083* | |
H191 | 0.1998 | 0.3118 | 0.6676 | 0.099* | |
H192 | 0.2722 | 0.2639 | 0.6619 | 0.099* | |
H193 | 0.1989 | 0.2508 | 0.5778 | 0.099* | |
H211 | 0.4525 | 0.3699 | 0.5152 | 0.110* | |
H212 | 0.4267 | 0.3125 | 0.5897 | 0.110* | |
H213 | 0.4572 | 0.4250 | 0.6092 | 0.110* | |
H101 | 0.0683 | 0.5119 | 0.4050 | 0.048* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0909 (8) | 0.0524 (6) | 0.0757 (7) | 0.0101 (5) | 0.0229 (6) | 0.0302 (5) |
O1 | 0.0366 (5) | 0.0380 (5) | 0.0429 (5) | 0.0008 (4) | 0.0121 (4) | 0.0059 (4) |
O2 | 0.0629 (7) | 0.0470 (6) | 0.0611 (7) | −0.0145 (5) | 0.0072 (6) | 0.0083 (5) |
O3 | 0.0591 (7) | 0.0570 (7) | 0.0517 (7) | −0.0048 (5) | 0.0074 (5) | 0.0223 (5) |
O4 | 0.0446 (6) | 0.0502 (7) | 0.0650 (7) | −0.0019 (5) | 0.0066 (5) | 0.0015 (5) |
O5 | 0.0446 (6) | 0.0405 (6) | 0.1084 (11) | 0.0068 (5) | 0.0165 (6) | 0.0137 (6) |
N1 | 0.0377 (6) | 0.0401 (7) | 0.0418 (6) | −0.0047 (5) | 0.0121 (5) | 0.0030 (5) |
C1 | 0.0338 (7) | 0.0376 (7) | 0.0336 (7) | 0.0018 (5) | 0.0099 (5) | −0.0004 (5) |
C2 | 0.0391 (7) | 0.0353 (7) | 0.0300 (6) | −0.0017 (6) | 0.0095 (5) | −0.0000 (5) |
C3 | 0.0438 (8) | 0.0349 (7) | 0.0330 (7) | −0.0000 (6) | 0.0115 (6) | 0.0014 (5) |
C4 | 0.0434 (8) | 0.0355 (7) | 0.0389 (7) | 0.0029 (6) | 0.0126 (6) | 0.0030 (6) |
C5 | 0.0398 (7) | 0.0343 (7) | 0.0322 (7) | 0.0000 (6) | 0.0144 (5) | −0.0005 (5) |
C6 | 0.0415 (8) | 0.0404 (8) | 0.0443 (8) | −0.0013 (6) | 0.0129 (6) | −0.0008 (6) |
C7 | 0.0570 (9) | 0.0387 (8) | 0.0525 (9) | −0.0084 (7) | 0.0204 (7) | 0.0026 (7) |
C8 | 0.0649 (10) | 0.0390 (8) | 0.0448 (8) | 0.0072 (7) | 0.0202 (7) | 0.0099 (7) |
C9 | 0.0465 (8) | 0.0528 (9) | 0.0401 (8) | 0.0037 (7) | 0.0113 (6) | 0.0086 (7) |
C10 | 0.0415 (8) | 0.0460 (8) | 0.0366 (7) | −0.0025 (6) | 0.0128 (6) | 0.0040 (6) |
C11 | 0.0361 (7) | 0.0455 (8) | 0.0461 (8) | 0.0026 (6) | 0.0139 (6) | 0.0105 (7) |
C12 | 0.0281 (6) | 0.0467 (8) | 0.0442 (8) | −0.0013 (6) | 0.0123 (5) | 0.0066 (6) |
C13 | 0.0439 (8) | 0.0505 (9) | 0.0553 (9) | 0.0038 (7) | 0.0178 (7) | 0.0038 (8) |
C14 | 0.0670 (11) | 0.0711 (13) | 0.0570 (11) | −0.0030 (9) | 0.0207 (9) | −0.0118 (9) |
C15 | 0.0714 (12) | 0.0956 (16) | 0.0411 (9) | −0.0080 (11) | 0.0165 (8) | 0.0010 (10) |
C16 | 0.0643 (11) | 0.0677 (12) | 0.0476 (9) | −0.0102 (9) | 0.0138 (8) | 0.0156 (9) |
C17 | 0.0498 (9) | 0.0485 (9) | 0.0457 (9) | −0.0071 (7) | 0.0142 (7) | 0.0059 (7) |
C18 | 0.0493 (8) | 0.0363 (8) | 0.0401 (8) | 0.0009 (7) | 0.0149 (6) | 0.0022 (6) |
C19 | 0.0840 (15) | 0.0785 (14) | 0.0831 (14) | −0.0022 (11) | 0.0183 (11) | 0.0480 (12) |
C20 | 0.0428 (8) | 0.0405 (8) | 0.0459 (8) | 0.0030 (7) | 0.0124 (7) | 0.0045 (6) |
C21 | 0.0502 (11) | 0.0591 (13) | 0.164 (2) | 0.0181 (9) | 0.0179 (13) | 0.0285 (14) |
Geometric parameters (Å, º) top
F1—C8 | 1.3618 (18) | C12—C13 | 1.388 (2) |
O1—C1 | 1.3734 (15) | C12—C17 | 1.388 (2) |
O1—C4 | 1.3558 (17) | C13—C14 | 1.377 (2) |
O2—C18 | 1.2053 (19) | C14—C15 | 1.382 (3) |
O3—C18 | 1.3170 (17) | C15—C16 | 1.364 (3) |
O3—C19 | 1.451 (2) | C16—C17 | 1.394 (2) |
O4—C20 | 1.1960 (18) | N1—H101 | 0.972 |
O5—C20 | 1.3251 (19) | C6—H6 | 0.970 |
O5—C21 | 1.442 (2) | C7—H7 | 0.970 |
N1—C2 | 1.4002 (17) | C9—H9 | 0.970 |
N1—C11 | 1.470 (2) | C10—H10 | 0.970 |
C1—C2 | 1.373 (2) | C11—H111 | 0.970 |
C1—C5 | 1.4604 (19) | C11—H112 | 0.970 |
C2—C3 | 1.4404 (18) | C13—H13 | 0.970 |
C3—C4 | 1.361 (2) | C14—H14 | 0.970 |
C3—C18 | 1.473 (2) | C15—H15 | 0.970 |
C4—C20 | 1.477 (2) | C16—H16 | 0.970 |
C5—C6 | 1.391 (2) | C17—H17 | 0.970 |
C5—C10 | 1.3963 (17) | C19—H191 | 0.970 |
C6—C7 | 1.385 (2) | C19—H192 | 0.970 |
C7—C8 | 1.369 (2) | C19—H193 | 0.970 |
C8—C9 | 1.371 (2) | C21—H211 | 0.970 |
C9—C10 | 1.380 (2) | C21—H212 | 0.970 |
C11—C12 | 1.514 (2) | C21—H213 | 0.970 |
| | | |
C1—O1—C4 | 107.86 (11) | O4—C20—C4 | 124.15 (14) |
C18—O3—C19 | 116.18 (13) | O5—C20—C4 | 110.91 (12) |
C20—O5—C21 | 115.71 (12) | C2—N1—H101 | 109.3 |
C2—N1—C11 | 116.19 (11) | C11—N1—H101 | 112.2 |
O1—C1—C2 | 109.19 (11) | C5—C6—H6 | 119.3 |
O1—C1—C5 | 116.38 (12) | C7—C6—H6 | 120.0 |
C2—C1—C5 | 134.31 (11) | C6—C7—H7 | 120.8 |
N1—C2—C1 | 126.09 (12) | C8—C7—H7 | 120.6 |
N1—C2—C3 | 127.60 (13) | C8—C9—H9 | 120.7 |
C1—C2—C3 | 106.30 (12) | C10—C9—H9 | 121.2 |
C2—C3—C4 | 106.22 (12) | C5—C10—H10 | 119.1 |
C2—C3—C18 | 123.40 (13) | C9—C10—H10 | 119.7 |
C4—C3—C18 | 130.35 (13) | N1—C11—H111 | 106.9 |
O1—C4—C3 | 110.38 (11) | N1—C11—H112 | 107.8 |
O1—C4—C20 | 114.06 (13) | C12—C11—H111 | 107.5 |
C3—C4—C20 | 135.55 (13) | C12—C11—H112 | 107.6 |
C1—C5—C6 | 120.49 (11) | H111—C11—H112 | 109.5 |
C1—C5—C10 | 120.92 (12) | C12—C13—H13 | 118.9 |
C6—C5—C10 | 118.54 (12) | C14—C13—H13 | 120.1 |
C5—C6—C7 | 120.65 (13) | C13—C14—H14 | 120.0 |
C6—C7—C8 | 118.59 (16) | C15—C14—H14 | 119.8 |
F1—C8—C7 | 118.25 (15) | C14—C15—H15 | 120.1 |
F1—C8—C9 | 118.89 (14) | C16—C15—H15 | 120.0 |
C7—C8—C9 | 122.86 (14) | C15—C16—H16 | 119.7 |
C8—C9—C10 | 118.07 (13) | C17—C16—H16 | 120.1 |
C5—C10—C9 | 121.25 (14) | C12—C17—H17 | 119.4 |
N1—C11—C12 | 117.40 (12) | C16—C17—H17 | 120.1 |
C11—C12—C13 | 119.51 (14) | O3—C19—H191 | 109.5 |
C11—C12—C17 | 122.15 (14) | O3—C19—H192 | 109.7 |
C13—C12—C17 | 118.28 (15) | O3—C19—H193 | 109.2 |
C12—C13—C14 | 120.95 (16) | H191—C19—H192 | 109.5 |
C13—C14—C15 | 120.18 (18) | H191—C19—H193 | 109.5 |
C14—C15—C16 | 119.82 (18) | H192—C19—H193 | 109.5 |
C15—C16—C17 | 120.27 (18) | O5—C21—H211 | 109.5 |
C12—C17—C16 | 120.46 (16) | O5—C21—H212 | 109.7 |
O2—C18—O3 | 124.01 (15) | O5—C21—H213 | 109.3 |
O2—C18—C3 | 122.49 (12) | H211—C21—H212 | 109.5 |
O3—C18—C3 | 113.45 (13) | H211—C21—H213 | 109.5 |
O4—C20—O5 | 124.93 (13) | H212—C21—H213 | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···O2 | 0.97 | 2.28 | 3.009 (2) | 132 |
C13—H13···O4i | 0.97 | 2.49 | 3.392 (2) | 155 |
C15—H15···O2ii | 0.97 | 2.47 | 3.430 (2) | 172 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, −y+1, z+1/2. |
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