Methyl 4-{[(1Z)-1-benzoyl-3-oxo-3-phenylprop-1-en-1-yl]amino}benzoate

The title compound, C₂₄H₁₉NO₄, was obtained as a by-product in the synthesis of 1-phenyl-4-nitro­phenyl­propane-1,3-dione. The crystal structure is stabilized by several inter- and intra­molecular C—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.061
• wR factor = 0.144
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 4-{[(1Z)-1-benzoyl-3-oxo-3-phenylprop-1-en-1-yl]amino}benzoate

Crystal data

C24H19NO4	F(000) = 808
Mr = 385.4	Dx = 1.365 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3059 reflections
a = 10.0396 (5) Å	θ = 2.3–28.3°
b = 9.8912 (5) Å	µ = 0.09 mm^−1
c = 18.9631 (9) Å	T = 100 K
β = 94.965 (3)°	Block, yellow
V = 1876.04 (16) Å^3	0.2 × 0.13 × 0.09 mm
Z = 4

Data collection

Bruker X8 APEXII 4K diffractometer	4606 independent reflections
Graphite monochromator	3462 reflections with I > 2σ(I)
Detector resolution: 512 pixels mm^-1	Rint = 0.046
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.982, Tmax = 0.992	k = −12→13
13970 measured reflections	l = −25→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.061	w = 1/[σ^2(Fo^2) + (0.0588P)^2 + 0.8797P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.144	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.34 e Å^−3
4606 reflections	Δρmin = −0.27 e Å^−3
267 parameters

Special details

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K diffractometer using an exposure time of 60 s/frame. A total of 901 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 97.9% completeness accomplished.

¹H NMR (300 MHz, CDCl₃): δ 3.86 (3H, s, CH₃), 6.23 (1H, s, CH), 7.00 (2H, d, ³J = 9 Hz, C₆H₄), 7.49 (6H, m, C₆H₅), 7.86 (2H, d, ³J = 9 Hz, C₆H₄), 7.98 (4H, m, C₆H₅)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8626 (2)	−0.0769 (2)	0.87218 (10)	0.0320 (5)
H1A	0.9523	−0.0507	0.8606	0.048*
H1B	0.8652	−0.1689	0.8913	0.048*
H1C	0.8322	−0.0143	0.9075	0.048*
C2	0.7033 (2)	0.0431 (2)	0.79677 (9)	0.0174 (4)
C3	0.6112 (2)	0.03525 (19)	0.73157 (9)	0.0170 (4)
C4	0.6122 (2)	−0.0731 (2)	0.68468 (9)	0.0182 (4)
H4	0.6729	−0.1458	0.6944	0.022*
C5	0.5251 (2)	−0.0754 (2)	0.62396 (9)	0.0185 (4)
H5	0.5262	−0.1496	0.5922	0.022*
C6	0.43590 (19)	0.03071 (19)	0.60923 (9)	0.0167 (4)
C7	0.4309 (2)	0.1366 (2)	0.65741 (9)	0.0202 (4)
H7	0.3668	0.2066	0.6491	0.024*
C8	0.5196 (2)	0.1393 (2)	0.71743 (9)	0.0201 (4)
H8	0.518	0.2132	0.7494	0.024*
C9	0.2842 (2)	0.12645 (19)	0.51204 (9)	0.0175 (4)
C10	0.3341 (2)	0.27011 (19)	0.52410 (9)	0.0173 (4)
C11	0.2415 (2)	0.37359 (19)	0.54751 (9)	0.0174 (4)
C12	0.1182 (2)	0.3377 (2)	0.57072 (10)	0.0220 (4)
H12	0.0916	0.2456	0.5706	0.026*
C13	0.0348 (2)	0.4364 (2)	0.59396 (10)	0.0246 (4)
H13	−0.049	0.4119	0.6099	0.029*
C14	0.0731 (2)	0.5703 (2)	0.59405 (10)	0.0232 (4)
H14	0.0155	0.6379	0.61	0.028*
C15	0.1960 (2)	0.6065 (2)	0.57080 (10)	0.0239 (5)
H15	0.2217	0.6989	0.5706	0.029*
C16	0.2802 (2)	0.5091 (2)	0.54814 (9)	0.0192 (4)
H16	0.3645	0.534	0.533	0.023*
C17	0.1881 (2)	0.1073 (2)	0.45782 (9)	0.0184 (4)
H17	0.1429	0.1845	0.4379	0.022*
C18	0.1510 (2)	−0.0242 (2)	0.42880 (9)	0.0190 (4)
C19	0.0453 (2)	−0.02757 (19)	0.36781 (9)	0.0180 (4)
C20	−0.0602 (2)	0.0635 (2)	0.36431 (10)	0.0229 (4)
H20	−0.0665	0.1277	0.4012	0.028*
C21	−0.1566 (2)	0.0614 (2)	0.30726 (11)	0.0274 (5)
H21	−0.2288	0.1237	0.3052	0.033*
C22	−0.1475 (2)	−0.0312 (2)	0.25364 (11)	0.0306 (5)
H22	−0.2125	−0.0317	0.2142	0.037*
C23	−0.0439 (2)	−0.1231 (2)	0.25727 (11)	0.0299 (5)
H23	−0.0386	−0.1875	0.2205	0.036*
C24	0.0531 (2)	−0.1223 (2)	0.31447 (10)	0.0236 (4)
H24	0.124	−0.1862	0.3169	0.028*
N	0.35095 (17)	0.02378 (17)	0.54652 (8)	0.0185 (4)
O1	0.77149 (15)	−0.07201 (15)	0.80900 (7)	0.0256 (4)
O2	0.71416 (15)	0.14014 (14)	0.83548 (7)	0.0235 (3)
O3	0.44788 (14)	0.29599 (14)	0.51058 (7)	0.0209 (3)
O4	0.20445 (15)	−0.13062 (14)	0.45119 (7)	0.0253 (3)
H1	0.327 (2)	−0.056 (2)	0.5293 (11)	0.022 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0344 (14)	0.0390 (13)	0.0206 (9)	0.0117 (11)	−0.0092 (9)	0.0008 (9)
C2	0.0166 (10)	0.0200 (10)	0.0156 (8)	−0.0012 (8)	0.0014 (7)	0.0044 (7)
C3	0.0186 (10)	0.0176 (10)	0.0149 (8)	−0.0002 (8)	0.0025 (7)	0.0025 (6)
C4	0.0193 (10)	0.0172 (9)	0.0183 (8)	0.0036 (8)	0.0019 (7)	0.0034 (7)
C5	0.0226 (11)	0.0166 (9)	0.0165 (8)	−0.0006 (8)	0.0031 (7)	−0.0011 (7)
C6	0.0163 (10)	0.0186 (9)	0.0149 (8)	−0.0010 (8)	0.0004 (7)	0.0025 (7)
C7	0.0240 (11)	0.0189 (10)	0.0177 (8)	0.0062 (8)	0.0014 (8)	0.0007 (7)
C8	0.0259 (11)	0.0193 (10)	0.0151 (8)	0.0017 (8)	0.0023 (7)	−0.0006 (7)
C9	0.0178 (10)	0.0194 (10)	0.0155 (8)	0.0004 (8)	0.0028 (7)	−0.0008 (7)
C10	0.0196 (10)	0.0199 (10)	0.0117 (7)	−0.0006 (8)	−0.0036 (7)	0.0010 (7)
C11	0.0200 (10)	0.0191 (10)	0.0127 (7)	0.0010 (8)	−0.0017 (7)	0.0002 (6)
C12	0.0230 (11)	0.0215 (10)	0.0217 (9)	−0.0011 (8)	0.0029 (8)	−0.0008 (7)
C13	0.0210 (11)	0.0275 (11)	0.0260 (9)	0.0023 (9)	0.0062 (8)	0.0005 (8)
C14	0.0247 (12)	0.0223 (10)	0.0226 (9)	0.0078 (9)	0.0027 (8)	0.0009 (8)
C15	0.0310 (12)	0.0177 (10)	0.0227 (9)	0.0027 (9)	−0.0005 (8)	0.0019 (7)
C16	0.0201 (11)	0.0203 (10)	0.0169 (8)	−0.0004 (8)	0.0005 (7)	0.0021 (7)
C17	0.0196 (11)	0.0160 (9)	0.0189 (8)	0.0001 (8)	−0.0017 (7)	0.0001 (7)
C18	0.0193 (10)	0.0201 (10)	0.0174 (8)	−0.0021 (8)	0.0009 (7)	−0.0009 (7)
C19	0.0194 (10)	0.0180 (9)	0.0166 (8)	−0.0070 (8)	0.0015 (7)	0.0015 (7)
C20	0.0221 (11)	0.0217 (10)	0.0247 (9)	−0.0040 (9)	0.0007 (8)	−0.0033 (8)
C21	0.0177 (11)	0.0303 (12)	0.0332 (10)	−0.0011 (9)	−0.0026 (9)	−0.0003 (9)
C22	0.0243 (12)	0.0440 (14)	0.0224 (9)	−0.0079 (10)	−0.0039 (9)	−0.0023 (9)
C23	0.0310 (13)	0.0358 (13)	0.0227 (9)	−0.0061 (10)	0.0014 (9)	−0.0108 (9)
C24	0.0255 (12)	0.0223 (11)	0.0233 (9)	−0.0015 (9)	0.0041 (8)	−0.0032 (8)
N	0.0235 (10)	0.0158 (8)	0.0157 (7)	0.0000 (7)	−0.0020 (7)	−0.0019 (6)
O1	0.0293 (9)	0.0290 (8)	0.0171 (6)	0.0100 (7)	−0.0065 (6)	−0.0011 (5)
O2	0.0290 (9)	0.0210 (8)	0.0199 (6)	−0.0029 (6)	−0.0025 (6)	−0.0006 (5)
O3	0.0180 (8)	0.0235 (8)	0.0209 (6)	−0.0018 (6)	0.0005 (5)	−0.0027 (5)
O4	0.0313 (9)	0.0179 (7)	0.0256 (7)	0.0016 (6)	−0.0041 (6)	0.0014 (5)

Geometric parameters (Å, º)

C1—O1	1.444 (2)	C12—C13	1.383 (3)
C1—H1A	0.98	C12—H12	0.95
C1—H1B	0.98	C13—C14	1.378 (3)
C1—H1C	0.98	C13—H13	0.95
C2—O2	1.207 (2)	C14—C15	1.392 (3)
C2—O1	1.338 (2)	C14—H14	0.95
C2—C3	1.481 (2)	C15—C16	1.375 (3)
C3—C8	1.390 (3)	C15—H15	0.95
C3—C4	1.393 (3)	C16—H16	0.95
C4—C5	1.384 (2)	C17—C18	1.448 (3)
C4—H4	0.95	C17—H17	0.95
C5—C6	1.392 (3)	C18—O4	1.240 (2)
C5—H5	0.95	C18—C19	1.501 (3)
C6—C7	1.393 (3)	C19—C24	1.386 (3)
C6—N	1.404 (2)	C19—C20	1.388 (3)
C7—C8	1.384 (3)	C20—C21	1.388 (3)
C7—H7	0.95	C20—H20	0.95
C8—H8	0.95	C21—C22	1.377 (3)
C9—N	1.353 (2)	C21—H21	0.95
C9—C17	1.361 (3)	C22—C23	1.378 (3)
C9—C10	1.517 (3)	C22—H22	0.95
C10—O3	1.220 (2)	C23—C24	1.394 (3)
C10—C11	1.476 (3)	C23—H23	0.95
C11—C12	1.395 (3)	C24—H24	0.95
C11—C16	1.396 (3)	N—H1	0.88 (2)
O1—C1—H1A	109.5	C14—C13—H13	119.9
O1—C1—H1B	109.5	C12—C13—H13	119.9
H1A—C1—H1B	109.5	C13—C14—C15	120.08 (19)
O1—C1—H1C	109.5	C13—C14—H14	120
H1A—C1—H1C	109.5	C15—C14—H14	120
H1B—C1—H1C	109.5	C16—C15—C14	120.3 (2)
O2—C2—O1	123.59 (17)	C16—C15—H15	119.9
O2—C2—C3	124.49 (18)	C14—C15—H15	119.9
O1—C2—C3	111.90 (16)	C15—C16—C11	119.8 (2)
C8—C3—C4	119.20 (17)	C15—C16—H16	120.1
C8—C3—C2	118.48 (17)	C11—C16—H16	120.1
C4—C3—C2	122.32 (17)	C9—C17—C18	123.66 (18)
C5—C4—C3	120.29 (18)	C9—C17—H17	118.2
C5—C4—H4	119.9	C18—C17—H17	118.2
C3—C4—H4	119.9	O4—C18—C17	122.89 (17)
C4—C5—C6	120.24 (17)	O4—C18—C19	120.07 (17)
C4—C5—H5	119.9	C17—C18—C19	117.03 (17)
C6—C5—H5	119.9	C24—C19—C20	119.69 (18)
C5—C6—C7	119.59 (17)	C24—C19—C18	119.77 (18)
C5—C6—N	117.80 (17)	C20—C19—C18	120.54 (17)
C7—C6—N	122.58 (17)	C21—C20—C19	120.32 (19)
C8—C7—C6	119.82 (18)	C21—C20—H20	119.8
C8—C7—H7	120.1	C19—C20—H20	119.8
C6—C7—H7	120.1	C22—C21—C20	120.0 (2)
C7—C8—C3	120.77 (18)	C22—C21—H21	120
C7—C8—H8	119.6	C20—C21—H21	120
C3—C8—H8	119.6	C21—C22—C23	119.96 (19)
N—C9—C17	123.33 (18)	C21—C22—H22	120
N—C9—C10	119.14 (16)	C23—C22—H22	120
C17—C9—C10	116.57 (16)	C22—C23—C24	120.58 (19)
O3—C10—C11	122.91 (18)	C22—C23—H23	119.7
O3—C10—C9	117.87 (17)	C24—C23—H23	119.7
C11—C10—C9	119.12 (17)	C19—C24—C23	119.5 (2)
C12—C11—C16	119.70 (18)	C19—C24—H24	120.3
C12—C11—C10	121.16 (18)	C23—C24—H24	120.3
C16—C11—C10	119.12 (18)	C9—N—C6	127.71 (17)
C13—C12—C11	119.97 (19)	C9—N—H1	112.7 (14)
C13—C12—H12	120	C6—N—H1	119.1 (14)
C11—C12—H12	120	C2—O1—C1	116.72 (16)
C14—C13—C12	120.1 (2)
O2—C2—C3—C8	−7.7 (3)	C13—C14—C15—C16	−0.5 (3)
O1—C2—C3—C8	170.72 (18)	C14—C15—C16—C11	0.9 (3)
O2—C2—C3—C4	173.1 (2)	C12—C11—C16—C15	−0.8 (3)
O1—C2—C3—C4	−8.5 (3)	C10—C11—C16—C15	−179.03 (16)
C8—C3—C4—C5	1.5 (3)	N—C9—C17—C18	−3.0 (3)
C2—C3—C4—C5	−179.27 (18)	C10—C9—C17—C18	165.61 (18)
C3—C4—C5—C6	0.1 (3)	C9—C17—C18—O4	−0.1 (3)
C4—C5—C6—C7	−2.6 (3)	C9—C17—C18—C19	−178.55 (18)
C4—C5—C6—N	179.32 (18)	O4—C18—C19—C24	−33.9 (3)
C5—C6—C7—C8	3.7 (3)	C17—C18—C19—C24	144.54 (19)
N—C6—C7—C8	−178.39 (18)	O4—C18—C19—C20	146.1 (2)
C6—C7—C8—C3	−2.1 (3)	C17—C18—C19—C20	−35.4 (3)
C4—C3—C8—C7	−0.4 (3)	C24—C19—C20—C21	−0.9 (3)
C2—C3—C8—C7	−179.72 (18)	C18—C19—C20—C21	178.98 (19)
N—C9—C10—O3	58.6 (2)	C19—C20—C21—C22	−0.2 (3)
C17—C9—C10—O3	−110.5 (2)	C20—C21—C22—C23	1.1 (3)
N—C9—C10—C11	−124.84 (18)	C21—C22—C23—C24	−0.8 (4)
C17—C9—C10—C11	66.0 (2)	C20—C19—C24—C23	1.2 (3)
O3—C10—C11—C12	−172.08 (17)	C18—C19—C24—C23	−178.67 (19)
C9—C10—C11—C12	11.6 (2)	C22—C23—C24—C19	−0.4 (3)
O3—C10—C11—C16	6.1 (3)	C17—C9—N—C6	−169.39 (19)
C9—C10—C11—C16	−170.22 (16)	C10—C9—N—C6	22.2 (3)
C16—C11—C12—C13	0.2 (3)	C5—C6—N—C9	−160.62 (19)
C10—C11—C12—C13	178.45 (17)	C7—C6—N—C9	21.4 (3)
C11—C12—C13—C14	0.2 (3)	O2—C2—O1—C1	−0.3 (3)
C12—C13—C14—C15	−0.1 (3)	C3—C2—O1—C1	−178.74 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···O4	0.88 (2)	1.99 (2)	2.703 (2)	138 (2)
C1—H1B···O3^i	0.98	2.55	3.068 (2)	113
C1—H1C···O2	0.98	2.31	2.671 (3)	101
C4—H4···O2^i	0.95	2.49	3.368 (2)	154
C5—H5···O3^ii	0.95	2.46	3.386 (2)	165

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