1-Benzamido-2-(2-fur­yl)-3-phenyl­cyclo­propane­carboxylic acid

The mol­ecule of the title compound, C₂₁H₁₇NO₄, exhibits a trans arrangement of the furyl and phenyl substituents on the cyclo­propane ring. The crystal structure is stabilized by inter­molecular O—H...O hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 284 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.085
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C7      ..       5.14 su
PLAT320_ALERT_2_C Check Hybridisation of  C10    in Main Residue .          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H101   ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   3 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Benzamido-2-(2-furyl)-3-phenylcyclopropanecarboxylic acid

Crystal data

C21H17NO4	F(000) = 728
Mr = 347.36	Dx = 1.355 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 36 reflections
a = 9.134 (2) Å	θ = 2.3–13.1°
b = 10.641 (3) Å	µ = 0.09 mm^−1
c = 17.696 (5) Å	T = 284 K
β = 98.04 (2)°	Block, colourless
V = 1703.1 (8) Å^3	0.58 × 0.46 × 0.18 mm
Z = 4

Data collection

Siemens P4 diffractometer	Rint = 0.017
Radiation source: normal-focus sealed tube	θmax = 27.0°, θmin = 2.2°
Graphite monochromator	h = 0→11
ω scans	k = 0→13
4308 measured reflections	l = −22→22
3716 independent reflections	3 standard reflections every 97 reflections
1987 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0216P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
3716 reflections	Δρmax = 0.22 e Å^−3
244 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.12980 (14)	0.18381 (12)	0.74206 (7)	0.0406 (4)
O2	0.61743 (15)	0.49091 (12)	0.69260 (7)	0.0379 (4)
O3	0.65878 (16)	0.15595 (13)	0.81600 (7)	0.0421 (4)
O4	0.63647 (16)	0.17160 (14)	0.68908 (8)	0.0519 (4)
N1	0.42613 (18)	0.35769 (16)	0.68463 (9)	0.0325 (4)
C1	0.4666 (2)	0.6395 (2)	0.57247 (12)	0.0498 (6)
H1	0.5505	0.6738	0.6009	0.060*
C2	0.3937 (3)	0.7053 (2)	0.51076 (14)	0.0678 (8)
H2	0.4280	0.7842	0.4990	0.081*
C3	0.2731 (3)	0.6563 (3)	0.46736 (13)	0.0574 (7)
H3	0.2260	0.7007	0.4257	0.069*
C4	0.2216 (3)	0.5421 (3)	0.48508 (13)	0.0675 (8)
H4	0.1387	0.5081	0.4557	0.081*
C5	0.2928 (3)	0.4763 (2)	0.54695 (12)	0.0615 (7)
H5	0.2570	0.3979	0.5587	0.074*
C6	0.4160 (2)	0.52463 (18)	0.59176 (10)	0.0319 (5)
C7	0.4962 (2)	0.45752 (18)	0.65923 (10)	0.0299 (5)
C8	0.4802 (2)	0.29543 (17)	0.75480 (10)	0.0296 (5)
C9	0.36108 (19)	0.26244 (18)	0.80545 (10)	0.0316 (5)
H9	0.3813	0.1870	0.8370	0.038*
C10	0.4629 (2)	0.36961 (18)	0.82647 (10)	0.0315 (5)
H10	0.4144	0.4508	0.8146	0.038*
C11	0.5997 (2)	0.20313 (18)	0.74898 (12)	0.0328 (5)
C12	0.2048 (2)	0.28434 (19)	0.77655 (11)	0.0328 (5)
C13	0.1147 (2)	0.3833 (2)	0.77355 (13)	0.0558 (7)
H13	0.1393	0.4633	0.7924	0.067*
C14	−0.0264 (2)	0.3440 (2)	0.73621 (13)	0.0521 (6)
H14	−0.1116	0.3926	0.7264	0.063*
C15	−0.0115 (2)	0.2245 (2)	0.71838 (12)	0.0444 (6)
H15	−0.0867	0.1748	0.6932	0.053*
C16	0.5729 (2)	0.37547 (18)	0.89739 (11)	0.0326 (5)
C17	0.5379 (2)	0.3344 (2)	0.96626 (12)	0.0494 (6)
H17	0.4471	0.2962	0.9686	0.059*
C18	0.6378 (3)	0.3499 (2)	1.03234 (13)	0.0633 (8)
H18	0.6131	0.3225	1.0789	0.076*
C19	0.7717 (3)	0.4049 (3)	1.02947 (14)	0.0687 (8)
H19	0.8389	0.4142	1.0737	0.082*
C20	0.8062 (3)	0.4465 (2)	0.96078 (14)	0.0638 (8)
H20	0.8970	0.4847	0.9585	0.077*
C21	0.7076 (2)	0.4320 (2)	0.89531 (12)	0.0449 (6)
H21	0.7323	0.4607	0.8491	0.054*
H3O	0.741 (3)	0.097 (2)	0.8087 (12)	0.080 (8)*
H101	0.337 (2)	0.3400 (19)	0.6641 (11)	0.055 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0312 (8)	0.0355 (9)	0.0538 (9)	−0.0011 (7)	0.0013 (7)	−0.0022 (7)
O2	0.0349 (8)	0.0387 (9)	0.0383 (8)	−0.0108 (7)	−0.0011 (6)	0.0040 (7)
O3	0.0461 (9)	0.0422 (9)	0.0371 (9)	0.0162 (8)	0.0021 (7)	0.0022 (7)
O4	0.0528 (10)	0.0624 (11)	0.0410 (9)	0.0198 (8)	0.0082 (8)	−0.0021 (8)
N1	0.0284 (10)	0.0337 (11)	0.0338 (10)	−0.0039 (9)	−0.0018 (8)	0.0081 (8)
C1	0.0502 (14)	0.0445 (15)	0.0519 (14)	−0.0058 (12)	−0.0030 (12)	0.0137 (12)
C2	0.0798 (19)	0.0526 (16)	0.0677 (18)	0.0002 (16)	−0.0020 (15)	0.0272 (14)
C3	0.0667 (18)	0.0658 (19)	0.0393 (14)	0.0257 (15)	0.0063 (13)	0.0151 (13)
C4	0.0662 (18)	0.082 (2)	0.0481 (16)	−0.0010 (17)	−0.0151 (13)	0.0083 (15)
C5	0.0666 (17)	0.0581 (17)	0.0525 (15)	−0.0148 (14)	−0.0169 (13)	0.0180 (13)
C6	0.0360 (12)	0.0328 (12)	0.0273 (11)	0.0042 (10)	0.0057 (9)	−0.0002 (9)
C7	0.0327 (11)	0.0269 (11)	0.0311 (11)	0.0024 (10)	0.0085 (9)	−0.0033 (9)
C8	0.0273 (10)	0.0264 (11)	0.0347 (11)	0.0001 (9)	0.0029 (9)	0.0037 (9)
C9	0.0307 (11)	0.0282 (11)	0.0362 (12)	−0.0006 (9)	0.0057 (9)	0.0051 (9)
C10	0.0298 (11)	0.0270 (11)	0.0370 (11)	0.0023 (9)	0.0023 (9)	0.0007 (9)
C11	0.0277 (11)	0.0323 (12)	0.0376 (12)	−0.0043 (9)	0.0017 (10)	0.0001 (10)
C12	0.0304 (11)	0.0299 (11)	0.0387 (12)	−0.0033 (10)	0.0063 (9)	−0.0002 (10)
C13	0.0397 (14)	0.0390 (14)	0.0862 (19)	0.0050 (12)	0.0003 (13)	−0.0083 (13)
C14	0.0295 (12)	0.0495 (16)	0.0758 (17)	0.0095 (12)	0.0019 (12)	0.0026 (13)
C15	0.0272 (12)	0.0534 (15)	0.0504 (14)	−0.0030 (12)	−0.0020 (10)	0.0055 (12)
C16	0.0362 (12)	0.0278 (11)	0.0332 (12)	0.0033 (10)	0.0025 (9)	−0.0012 (9)
C17	0.0475 (14)	0.0578 (16)	0.0439 (14)	0.0041 (12)	0.0101 (11)	0.0076 (12)
C18	0.083 (2)	0.0742 (19)	0.0325 (13)	0.0207 (17)	0.0066 (14)	0.0060 (13)
C19	0.081 (2)	0.069 (2)	0.0476 (17)	0.0103 (17)	−0.0201 (16)	−0.0147 (14)
C20	0.0575 (16)	0.0613 (18)	0.0658 (18)	−0.0141 (14)	−0.0156 (14)	−0.0026 (15)
C21	0.0411 (13)	0.0473 (14)	0.0438 (13)	−0.0090 (11)	−0.0029 (11)	0.0031 (11)

Geometric parameters (Å, º)

O1—C12	1.367 (2)	C8—C9	1.544 (2)
O1—C15	1.370 (2)	C9—C12	1.466 (2)
O2—C7	1.232 (2)	C9—C10	1.485 (2)
O3—C11	1.331 (2)	C9—H9	0.9800
O3—H3O	1.00 (2)	C10—C16	1.496 (2)
O4—C11	1.203 (2)	C10—H10	0.9800
N1—C7	1.349 (2)	C12—C13	1.333 (3)
N1—C8	1.433 (2)	C13—C14	1.426 (3)
N1—H101	0.866 (19)	C13—H13	0.9300
C1—C6	1.367 (3)	C14—C15	1.322 (3)
C1—C2	1.387 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.356 (3)	C16—C17	1.374 (3)
C2—H2	0.9300	C16—C21	1.374 (3)
C3—C4	1.355 (3)	C17—C18	1.388 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.383 (3)	C18—C19	1.363 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.382 (3)	C19—C20	1.371 (3)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.492 (3)	C20—C21	1.373 (3)
C8—C11	1.483 (3)	C20—H20	0.9300
C8—C10	1.521 (2)	C21—H21	0.9300
C12—O1—C15	106.33 (16)	C9—C10—C8	61.78 (12)
C11—O3—H3O	109.8 (12)	C16—C10—C8	125.84 (16)
C7—N1—C8	122.06 (16)	C9—C10—H10	112.0
C7—N1—H101	119.6 (14)	C16—C10—H10	112.0
C8—N1—H101	117.0 (14)	C8—C10—H10	112.0
C6—C1—C2	120.4 (2)	O4—C11—O3	123.47 (19)
C6—C1—H1	119.8	O4—C11—C8	123.01 (18)
C2—C1—H1	119.8	O3—C11—C8	113.49 (18)
C3—C2—C1	121.0 (2)	C13—C12—O1	109.42 (17)
C3—C2—H2	119.5	C13—C12—C9	134.8 (2)
C1—C2—H2	119.5	O1—C12—C9	115.72 (17)
C4—C3—C2	119.6 (2)	C12—C13—C14	107.4 (2)
C4—C3—H3	120.2	C12—C13—H13	126.3
C2—C3—H3	120.2	C14—C13—H13	126.3
C3—C4—C5	119.8 (2)	C15—C14—C13	106.0 (2)
C3—C4—H4	120.1	C15—C14—H14	127.0
C5—C4—H4	120.1	C13—C14—H14	127.0
C6—C5—C4	121.4 (2)	C14—C15—O1	110.8 (2)
C6—C5—H5	119.3	C14—C15—H15	124.6
C4—C5—H5	119.3	O1—C15—H15	124.6
C1—C6—C5	117.80 (19)	C17—C16—C21	118.89 (19)
C1—C6—C7	118.84 (18)	C17—C16—C10	121.24 (19)
C5—C6—C7	123.36 (19)	C21—C16—C10	119.67 (18)
O2—C7—N1	120.24 (17)	C16—C17—C18	120.2 (2)
O2—C7—C6	123.58 (18)	C16—C17—H17	119.9
N1—C7—C6	116.15 (17)	C18—C17—H17	119.9
N1—C8—C11	114.44 (16)	C19—C18—C17	120.4 (2)
N1—C8—C10	114.80 (16)	C19—C18—H18	119.8
C11—C8—C10	124.41 (16)	C17—C18—H18	119.8
N1—C8—C9	115.03 (15)	C18—C19—C20	119.4 (2)
C11—C8—C9	118.38 (16)	C18—C19—H19	120.3
C10—C8—C9	57.99 (12)	C20—C19—H19	120.3
C12—C9—C10	120.68 (17)	C19—C20—C21	120.5 (2)
C12—C9—C8	119.48 (16)	C19—C20—H20	119.8
C10—C9—C8	60.23 (12)	C21—C20—H20	119.8
C12—C9—H9	115.2	C20—C21—C16	120.7 (2)
C10—C9—H9	115.2	C20—C21—H21	119.7
C8—C9—H9	115.2	C16—C21—H21	119.7
C9—C10—C16	124.47 (17)
C6—C1—C2—C3	−1.4 (4)	N1—C8—C11—O4	−8.5 (3)
C1—C2—C3—C4	0.9 (4)	C10—C8—C11—O4	−158.96 (19)
C2—C3—C4—C5	−0.3 (4)	C9—C8—C11—O4	132.2 (2)
C3—C4—C5—C6	0.2 (4)	N1—C8—C11—O3	173.46 (16)
C2—C1—C6—C5	1.3 (3)	C10—C8—C11—O3	23.0 (3)
C2—C1—C6—C7	−179.1 (2)	C9—C8—C11—O3	−45.9 (2)
C4—C5—C6—C1	−0.7 (3)	C15—O1—C12—C13	−0.8 (2)
C4—C5—C6—C7	179.7 (2)	C15—O1—C12—C9	−178.99 (16)
C8—N1—C7—O2	6.8 (3)	C10—C9—C12—C13	−12.8 (3)
C8—N1—C7—C6	−171.13 (16)	C8—C9—C12—C13	−83.6 (3)
C1—C6—C7—O2	−10.5 (3)	C10—C9—C12—O1	164.89 (16)
C5—C6—C7—O2	169.1 (2)	C8—C9—C12—O1	94.0 (2)
C1—C6—C7—N1	167.40 (18)	O1—C12—C13—C14	0.9 (3)
C5—C6—C7—N1	−13.0 (3)	C9—C12—C13—C14	178.7 (2)
C7—N1—C8—C11	−81.8 (2)	C12—C13—C14—C15	−0.7 (3)
C7—N1—C8—C10	71.5 (2)	C13—C14—C15—O1	0.3 (3)
C7—N1—C8—C9	136.12 (18)	C12—O1—C15—C14	0.3 (2)
N1—C8—C9—C12	5.9 (3)	C9—C10—C16—C17	−41.2 (3)
C11—C8—C9—C12	−134.58 (19)	C8—C10—C16—C17	−119.0 (2)
C10—C8—C9—C12	110.6 (2)	C9—C10—C16—C21	144.11 (19)
N1—C8—C9—C10	−104.72 (18)	C8—C10—C16—C21	66.3 (3)
C11—C8—C9—C10	114.82 (19)	C21—C16—C17—C18	−0.2 (3)
C12—C9—C10—C16	135.40 (19)	C10—C16—C17—C18	−174.9 (2)
C8—C9—C10—C16	−115.9 (2)	C16—C17—C18—C19	−0.5 (4)
C12—C9—C10—C8	−108.66 (19)	C17—C18—C19—C20	0.9 (4)
N1—C8—C10—C9	105.11 (17)	C18—C19—C20—C21	−0.5 (4)
C11—C8—C10—C9	−104.5 (2)	C19—C20—C21—C16	−0.1 (4)
N1—C8—C10—C16	−141.02 (19)	C17—C16—C21—C20	0.5 (3)
C11—C8—C10—C16	9.3 (3)	C10—C16—C21—C20	175.3 (2)
C9—C8—C10—C16	113.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2^i	1.00 (2)	1.72 (2)	2.715 (2)	173 (2)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.