1-(3-Amino-1-benzo­furan-2-yl)-2-mesityl­ethano­ne

Arıcı, C.; Ülkü, D.; Kırılmış, C.; Koca, M.; Ahmedzade, M.

doi:10.1107/S160053680401428X

1-(3-Amino-1-benzofuran-2-yl)-2-mesitylethanone

C. Arıcı, D. Ülkü, C. Kırılmış, M. Koca and M. Ahmedzade

The title compound, C₁₉H₁₉NO₂, features a benzofuran ring system coplanar with an amino substituent and linked to a mesityl group by an acetyl bridge. In the crystal structure, symmetry-related molecules are linked by N—H

O intermolecular hydrogen bonds involving one amino H atom and the O atom of the acetyl group to form infinite chains. The other amino H atom is involved in an intramolecular hydrogen bond with the acetyl O atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401428X/ac6098sup1.cif Contains datablocks global, 2
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680401428X/ac60982sup2.hkl Contains datablock 2

CCDC reference: 245306

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.054
wR factor = 0.132
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      24.63 Deg.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           24.63
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2370
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2664
           Completeness (_total/calc)             88.96%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C4      ..       7.07 su
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H18C   ..  H19B    ..       2.01 Ang.

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5864
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.63 Deg.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C19     ..       5.81 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C17
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C19
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10B   ..  H19A    ..       1.83 Ang.

   2 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON2000 (A. L. Spek, 2000); software used to prepare material for publication: SHELXL97.

(2) top

Crystal data top

C₁₉H₁₉NO₂	F(000) = 624
M_r = 293.35	D_x = 1.234 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.3779 (12) Å	θ = 2.4–24.6°
b = 10.3151 (11) Å	µ = 0.08 mm⁻¹
c = 15.2789 (13) Å	T = 293 K
β = 105.116 (4)°	Prism, colourless
V = 1579.0 (3) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

CAD-4 EXPRESS (Enraf–Nonius, 1993) diffractometer	R_int = 0.046
ω/2θ scans	θ_max = 24.6°
Absorption correction: ψ scan empirical (using intensity measurements) via ψ scans (Fair, 1990)	h = −12→0
T_min = 0.981, T_max = 0.988	k = −12→0
2499 measured reflections	l = −17→17
2370 independent reflections	3 standard reflections every 120 min
1392 reflections with I > 2σ(I)	intensity decay: 0.7%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0639P)² + 1.0373P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2370 reflections	Δρ_max = 0.24 e Å⁻³
200 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.097 (19)

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.1455 (2)	0.3710 (2)	0.12700 (15)	0.0461 (7)
O2	0.4404 (2)	0.5653 (2)	0.16677 (17)	0.0538 (8)
N1	0.4633 (3)	0.3461 (3)	0.2915 (2)	0.0543 (9)
C1	0.2769 (3)	0.4131 (3)	0.1664 (2)	0.0412 (9)
C2	0.3389 (3)	0.3339 (3)	0.2372 (2)	0.0378 (9)
C3	0.2424 (3)	0.2361 (3)	0.2436 (2)	0.0379 (9)
C4	0.1275 (3)	0.2636 (3)	0.1756 (2)	0.0402 (9)
C5	0.0126 (4)	0.1923 (4)	0.1608 (3)	0.0466 (10)
C6	0.0141 (4)	0.0886 (4)	0.2179 (3)	0.0497 (10)
C7	0.1266 (4)	0.0577 (4)	0.2869 (2)	0.0490 (10)
C8	0.2416 (4)	0.1297 (3)	0.3002 (2)	0.0456 (10)
C9	0.3282 (4)	0.5208 (3)	0.1283 (2)	0.0411 (9)
C10	0.2502 (4)	0.5746 (3)	0.0383 (2)	0.0494 (10)
C11	0.2656 (3)	0.7194 (3)	0.0273 (2)	0.0393 (9)
C12	0.2019 (4)	0.8036 (4)	0.0740 (2)	0.0459 (10)
C13	0.2081 (4)	0.9362 (4)	0.0604 (3)	0.0521 (10)
C14	0.2745 (4)	0.9876 (4)	0.0015 (3)	0.0477 (10)
C15	0.3391 (4)	0.9035 (4)	−0.0430 (2)	0.0483 (10)
C16	0.3365 (3)	0.7694 (3)	−0.0314 (2)	0.0430 (9)
C17	0.1251 (5)	0.7534 (4)	0.1377 (3)	0.0819 (15)
C18	0.2747 (5)	1.1327 (4)	−0.0158 (3)	0.0768 (14)
C19	0.4086 (4)	0.6836 (4)	−0.0829 (3)	0.0724 (14)
H1A	0.5132	0.4092	0.2834	0.065*
H1B	0.4928	0.2909	0.3342	0.065*
H5	−0.0626	0.2128	0.1147	0.056*
H6	−0.0622	0.0379	0.2100	0.060*
H7	0.1239	−0.0125	0.3245	0.059*
H8	0.3172	0.1081	0.3458	0.055*
H10A	0.1564	0.5555	0.0306	0.059*
H10B	0.2783	0.5303	−0.0096	0.059*
H13	0.1661	0.9920	0.0920	0.062*
H15	0.3859	0.9373	−0.0821	0.058*
H17A	0.0885	0.8249	0.1634	0.123*
H17B	0.1838	0.7046	0.1853	0.123*
H17C	0.0541	0.6984	0.1051	0.123*
H18A	0.2245	1.1761	0.0202	0.115*
H18B	0.2348	1.1496	−0.0788	0.115*
H18C	0.3649	1.1642	0.0004	0.115*
H19A	0.3978	0.5946	−0.0680	0.109*
H19B	0.5017	0.7053	−0.0668	0.109*
H19C	0.3720	0.6963	−0.1468	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0419 (14)	0.0388 (15)	0.0495 (15)	0.0072 (12)	−0.0025 (12)	0.0012 (12)
O2	0.0468 (15)	0.0419 (15)	0.0632 (17)	0.0037 (13)	−0.0025 (13)	−0.0028 (13)
N1	0.0460 (19)	0.051 (2)	0.056 (2)	0.0101 (16)	−0.0047 (16)	−0.0045 (16)
C1	0.036 (2)	0.033 (2)	0.049 (2)	−0.0008 (18)	0.0019 (17)	0.0005 (17)
C2	0.037 (2)	0.033 (2)	0.041 (2)	−0.0013 (17)	0.0060 (17)	0.0048 (17)
C3	0.038 (2)	0.034 (2)	0.040 (2)	−0.0014 (17)	0.0081 (17)	0.0065 (17)
C4	0.043 (2)	0.032 (2)	0.044 (2)	0.0038 (17)	0.0084 (18)	0.0075 (18)
C5	0.039 (2)	0.047 (2)	0.048 (2)	−0.0022 (19)	0.0027 (18)	−0.0008 (19)
C6	0.049 (2)	0.045 (2)	0.057 (2)	−0.005 (2)	0.018 (2)	−0.005 (2)
C7	0.055 (2)	0.043 (2)	0.050 (2)	0.0050 (19)	0.015 (2)	0.000 (2)
C8	0.048 (2)	0.042 (2)	0.044 (2)	0.0063 (19)	0.0063 (17)	0.0043 (19)
C9	0.042 (2)	0.032 (2)	0.048 (2)	−0.0032 (17)	0.0071 (18)	0.0034 (18)
C10	0.058 (2)	0.037 (2)	0.046 (2)	0.0024 (18)	0.0014 (19)	−0.0028 (19)
C11	0.038 (2)	0.038 (2)	0.038 (2)	0.0012 (17)	0.0022 (17)	0.0002 (17)
C12	0.052 (2)	0.042 (2)	0.046 (2)	0.0060 (18)	0.0178 (19)	0.0027 (19)
C13	0.064 (3)	0.041 (2)	0.057 (2)	0.002 (2)	0.026 (2)	0.012 (2)
C14	0.053 (2)	0.034 (2)	0.055 (2)	0.0061 (19)	0.013 (2)	0.0025 (19)
C15	0.052 (2)	0.047 (2)	0.048 (2)	0.001 (2)	0.0163 (19)	−0.0077 (19)
C16	0.039 (2)	0.043 (2)	0.045 (2)	−0.0078 (18)	0.0081 (17)	−0.0042 (18)
C17	0.111 (4)	0.065 (3)	0.088 (3)	0.013 (3)	0.058 (3)	0.013 (3)
C18	0.093 (4)	0.044 (3)	0.096 (4)	0.014 (2)	0.029 (3)	−0.001 (2)
C19	0.075 (3)	0.063 (3)	0.090 (3)	−0.025 (3)	0.040 (3)	−0.013 (2)

Geometric parameters (Å, º) top

C1—C2	1.374 (5)	C11—C12	1.398 (5)
C1—O1	1.408 (4)	C12—C13	1.388 (5)
C1—C9	1.421 (5)	C12—C17	1.501 (5)
C2—N1	1.346 (4)	C13—C14	1.374 (5)
C2—C3	1.442 (2)	C13—H13	0.9300
C3—C4	1.391 (4)	C14—C15	1.379 (5)
C3—C8	1.399 (5)	C14—C18	1.520 (5)
C4—C5	1.370 (5)	C15—C16	1.396 (5)
C4—O1	1.373 (4)	C15—H15	0.9300
C5—C6	1.377 (5)	C16—C19	1.507 (5)
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.391 (5)	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.375 (5)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C9—O2	1.246 (4)	C19—H19A	0.9600
C9—C10	1.508 (5)	C19—H19B	0.9600
C10—C11	1.516 (5)	C19—H19C	0.9600
C10—H10A	0.9700	N1—H1A	0.8600
C10—H10B	0.9700	N1—H1B	0.8600
C11—C16	1.396 (5)

C2—C1—O1	110.8 (3)	C13—C12—C11	119.4 (4)
C2—C1—C9	129.7 (3)	C13—C12—C17	119.4 (4)
O1—C1—C9	119.4 (3)	C11—C12—C17	121.2 (3)
N1—C2—C1	127.3 (3)	C14—C13—C12	121.9 (4)
N1—C2—C3	126.5 (3)	C14—C13—H13	119.0
C1—C2—C3	106.2 (3)	C12—C13—H13	119.0
C4—C3—C8	118.7 (3)	C13—C14—C15	118.2 (4)
C4—C3—C2	106.3 (3)	C13—C14—C18	121.1 (4)
C8—C3—C2	135.0 (3)	C15—C14—C18	120.7 (4)
C5—C4—O1	125.4 (3)	C14—C15—C16	122.2 (4)
C5—C4—C3	123.6 (3)	C14—C15—H15	118.9
O1—C4—C3	111.0 (3)	C16—C15—H15	118.9
C4—C5—C6	116.6 (3)	C15—C16—C11	118.6 (3)
C4—C5—H5	121.7	C15—C16—C19	119.1 (4)
C6—C5—H5	121.7	C11—C16—C19	122.3 (3)
C5—C6—C7	121.8 (4)	C12—C17—H17A	109.5
C5—C6—H6	119.1	C12—C17—H17B	109.5
C7—C6—H6	119.1	H17A—C17—H17B	109.5
C8—C7—C6	120.9 (4)	C12—C17—H17C	109.5
C8—C7—H7	119.6	H17A—C17—H17C	109.5
C6—C7—H7	119.6	H17B—C17—H17C	109.5
C7—C8—C3	118.5 (3)	C14—C18—H18A	109.5
C7—C8—H8	120.8	C14—C18—H18B	109.5
C3—C8—H8	120.8	H18A—C18—H18B	109.5
O2—C9—C1	119.9 (3)	C14—C18—H18C	109.5
O2—C9—C10	120.5 (3)	H18A—C18—H18C	109.5
C1—C9—C10	119.5 (3)	H18B—C18—H18C	109.5
C9—C10—C11	114.6 (3)	C16—C19—H19A	109.5
C9—C10—H10A	108.6	C16—C19—H19B	109.5
C11—C10—H10A	108.6	H19A—C19—H19B	109.5
C9—C10—H10B	108.6	C16—C19—H19C	109.5
C11—C10—H10B	108.6	H19A—C19—H19C	109.5
H10A—C10—H10B	107.6	H19B—C19—H19C	109.5
C16—C11—C12	119.7 (3)	C4—O1—C1	105.6 (3)
C16—C11—C10	121.6 (3)	C2—N1—H1A	120.0
C12—C11—C10	118.6 (3)	C2—N1—H1B	120.0

O1—C1—C2—N1	−178.6 (3)	C1—C9—C10—C11	148.2 (3)
C9—C1—C2—C3	−176.8 (3)	C9—C10—C11—C12	−73.8 (4)
N1—C2—C3—C4	178.4 (3)	C9—C10—C11—C16	109.3 (4)
C1—C2—C3—C8	−179.4 (4)	C10—C11—C12—C13	−176.0 (3)
C2—C3—C4—C5	−179.2 (3)	C16—C11—C12—C17	−179.9 (3)
C8—C3—C4—O1	179.7 (3)	C17—C12—C13—C14	−178.6 (4)
O1—C4—C5—C6	−179.2 (3)	C12—C13—C14—C18	177.1 (4)
C2—C3—C8—C7	178.4 (4)	C18—C14—C15—C16	−177.4 (4)
C2—C1—C9—O2	−9.2 (6)	C14—C15—C16—C19	179.5 (3)
O1—C1—C9—O2	174.3 (3)	C10—C11—C16—C15	175.6 (3)
C2—C1—C9—C10	166.8 (4)	C12—C11—C16—C19	179.3 (3)
O1—C1—C9—C10	−9.7 (5)	C5—C4—O1—C1	179.2 (3)
O2—C9—C10—C11	−35.9 (5)	C9—C1—O1—C4	177.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.8600	2.3700	2.927 (4)	122.00
N1—H1B···O2ⁱ	0.8600	2.4300	3.076 (4)	133.00

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

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1-(3-Amino-1-benzo­furan-2-yl)-2-mesityl­ethano­ne

Supporting information

Key indicators

checkCIF/PLATON results

1-(3-Amino-1-benzofuran-2-yl)-2-mesitylethanone