Synthesis, characterization and crystal structure of methyl 2-(2-oxo-2H-chromen-4-yl­amino)­benzoate

A new coumarin derivative, methyl 2-(2-oxo-2H-chromen-4-yl­amino)­benzoate, has been synthesized and characterized.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.066
• wR factor = 0.158
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.200
           From the CIF: _refine_ls_abs_structure_Flack_su    0.700
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.37 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00769 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1       ..H14      .       1.97 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.908 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595          8 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.700 Report
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        75% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          4 Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).

Methyl 2-(2-oxo-2H-chromen-4-yl)benzoate

Crystal data

C17H13NO4	Dx = 1.448 Mg m^−3
Mr = 295.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2328 reflections
a = 12.7698 (16) Å	θ = 2.1–25.0°
b = 14.9212 (18) Å	µ = 0.10 mm^−1
c = 7.1087 (8) Å	T = 298 K
V = 1354.5 (3) Å^3	Prismatic, yellow
Z = 4	0.39 × 0.08 × 0.06 mm
F(000) = 616

Data collection

Bruker D8 Venture diffractometer	2096 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.102
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 25.0°, θmin = 2.1°
Tmin = 0.666, Tmax = 0.745	h = −15→15
35019 measured reflections	k = −17→17
2328 independent reflections	l = −7→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 1.5253P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2328 reflections	Δρmax = 0.25 e Å^−3
204 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Absolute structure: Flack x determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.2 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.4084 (3)	0.8237 (3)	0.3512 (7)	0.0553 (12)
O2	0.5181 (3)	0.7166 (2)	0.4363 (8)	0.0536 (12)
O3	1.0000 (3)	0.6344 (3)	0.4928 (7)	0.0527 (12)
O4	1.0759 (3)	0.7520 (3)	0.3698 (9)	0.0669 (15)
N1	0.7132 (3)	0.7623 (3)	0.5069 (7)	0.0364 (11)
H1	0.664 (4)	0.725 (4)	0.502 (8)	0.032 (15)*
C1	0.3280 (5)	0.7569 (5)	0.3295 (12)	0.067 (2)
H1A	0.349617	0.713581	0.237447	0.101*
H1B	0.264282	0.785039	0.288804	0.101*
H1C	0.316334	0.727407	0.447724	0.101*
C2	0.5005 (4)	0.7946 (4)	0.4076 (9)	0.0405 (13)
C3	0.5768 (4)	0.8683 (3)	0.4321 (8)	0.0367 (13)
C4	0.6811 (4)	0.8507 (3)	0.4842 (8)	0.0326 (11)
C5	0.7468 (4)	0.9226 (3)	0.5221 (8)	0.0387 (13)
H5	0.814613	0.912215	0.564520	0.046*
C6	0.7126 (5)	1.0084 (4)	0.4974 (10)	0.0477 (15)
H6	0.758040	1.055801	0.520819	0.057*
C7	0.6125 (5)	1.0258 (3)	0.4388 (11)	0.0539 (17)
H7	0.590562	1.084558	0.419550	0.065*
C8	0.5454 (4)	0.9566 (4)	0.4089 (10)	0.0476 (15)
H8	0.476977	0.968658	0.372170	0.057*
C9	0.8095 (4)	0.7251 (3)	0.5005 (8)	0.0325 (11)
C10	0.8978 (4)	0.7656 (3)	0.4380 (9)	0.0385 (13)
H10	0.894045	0.825120	0.399951	0.046*
C11	0.9952 (4)	0.7211 (4)	0.4284 (10)	0.0469 (15)
C12	0.9119 (4)	0.5900 (4)	0.5527 (9)	0.0401 (13)
C13	0.8153 (4)	0.6322 (3)	0.5592 (8)	0.0342 (12)
C14	0.7308 (4)	0.5799 (3)	0.6151 (8)	0.0371 (13)
H14	0.664447	0.605621	0.619064	0.045*
C15	0.7421 (6)	0.4924 (4)	0.6640 (9)	0.0467 (14)
H15	0.684223	0.458872	0.700802	0.056*
C16	0.8405 (5)	0.4536 (4)	0.6587 (10)	0.0549 (17)
H16	0.848964	0.394016	0.694065	0.066*
C17	0.9249 (5)	0.5021 (4)	0.6022 (11)	0.058 (2)
H17	0.990900	0.475834	0.597178	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.033 (2)	0.047 (2)	0.086 (3)	0.0037 (19)	−0.006 (2)	0.004 (2)
O2	0.034 (2)	0.034 (2)	0.093 (4)	−0.0002 (17)	0.001 (2)	0.001 (2)
O3	0.034 (2)	0.039 (2)	0.085 (3)	0.0077 (16)	−0.006 (2)	−0.011 (2)
O4	0.031 (2)	0.053 (3)	0.117 (4)	−0.009 (2)	0.014 (2)	−0.020 (3)
N1	0.028 (2)	0.024 (2)	0.057 (3)	0.0006 (18)	0.001 (2)	0.004 (2)
C1	0.034 (3)	0.073 (5)	0.095 (6)	−0.006 (3)	−0.002 (4)	0.000 (4)
C2	0.028 (3)	0.038 (3)	0.055 (4)	0.008 (2)	0.008 (3)	−0.001 (3)
C3	0.032 (3)	0.031 (3)	0.046 (3)	0.006 (2)	0.006 (2)	−0.002 (2)
C4	0.035 (3)	0.032 (2)	0.030 (3)	0.005 (2)	0.003 (2)	0.000 (2)
C5	0.035 (3)	0.034 (3)	0.047 (3)	0.000 (2)	−0.002 (3)	−0.002 (3)
C6	0.054 (4)	0.031 (3)	0.058 (4)	−0.004 (2)	0.004 (3)	−0.004 (3)
C7	0.056 (4)	0.025 (3)	0.081 (5)	0.011 (3)	0.005 (4)	0.001 (3)
C8	0.038 (3)	0.038 (3)	0.066 (4)	0.014 (2)	0.003 (3)	0.004 (3)
C9	0.032 (3)	0.028 (2)	0.037 (3)	0.002 (2)	−0.003 (2)	−0.003 (2)
C10	0.035 (3)	0.029 (3)	0.051 (3)	−0.001 (2)	−0.002 (3)	−0.003 (2)
C11	0.031 (3)	0.042 (3)	0.068 (4)	−0.001 (2)	−0.001 (3)	−0.021 (3)
C12	0.034 (3)	0.034 (3)	0.052 (3)	0.003 (2)	−0.009 (3)	−0.007 (3)
C13	0.035 (3)	0.028 (3)	0.040 (3)	0.005 (2)	−0.006 (2)	−0.005 (2)
C14	0.037 (3)	0.029 (3)	0.045 (3)	0.006 (2)	−0.001 (2)	−0.001 (2)
C15	0.057 (4)	0.035 (3)	0.048 (4)	−0.005 (3)	−0.001 (3)	0.002 (3)
C16	0.069 (4)	0.032 (3)	0.064 (4)	0.006 (3)	−0.018 (4)	0.004 (3)
C17	0.046 (3)	0.041 (4)	0.087 (5)	0.021 (3)	−0.024 (4)	−0.007 (3)

Geometric parameters (Å, º)

O1—C2	1.316 (7)	C6—H6	0.9300
O1—C1	1.440 (8)	C7—C8	1.358 (8)
O2—C2	1.203 (6)	C7—H7	0.9300
O3—C12	1.373 (7)	C8—H8	0.9300
O3—C11	1.374 (7)	C9—C10	1.353 (7)
O4—C11	1.204 (7)	C9—C13	1.450 (7)
N1—C9	1.351 (6)	C10—C11	1.412 (7)
N1—C4	1.391 (6)	C10—H10	0.9300
N1—H1	0.84 (6)	C12—C17	1.367 (8)
C1—H1A	0.9600	C12—C13	1.385 (7)
C1—H1B	0.9600	C13—C14	1.390 (7)
C1—H1C	0.9600	C14—C15	1.359 (7)
C2—C3	1.479 (7)	C14—H14	0.9300
C3—C8	1.387 (7)	C15—C16	1.385 (10)
C3—C4	1.407 (7)	C15—H15	0.9300
C4—C5	1.388 (7)	C16—C17	1.359 (10)
C5—C6	1.363 (8)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.370 (9)
C2—O1—C1	116.2 (5)	C7—C8—H8	119.3
C12—O3—C11	121.5 (4)	C3—C8—H8	119.3
C9—N1—C4	130.9 (4)	N1—C9—C10	125.8 (5)
C9—N1—H1	114 (4)	N1—C9—C13	115.5 (4)
C4—N1—H1	114 (4)	C10—C9—C13	118.6 (4)
O1—C1—H1A	109.5	C9—C10—C11	122.7 (5)
O1—C1—H1B	109.5	C9—C10—H10	118.7
H1A—C1—H1B	109.5	C11—C10—H10	118.7
O1—C1—H1C	109.5	O4—C11—O3	116.0 (5)
H1A—C1—H1C	109.5	O4—C11—C10	126.3 (6)
H1B—C1—H1C	109.5	O3—C11—C10	117.7 (5)
O2—C2—O1	122.5 (5)	C17—C12—O3	116.3 (5)
O2—C2—C3	125.2 (5)	C17—C12—C13	122.4 (6)
O1—C2—C3	112.3 (4)	O3—C12—C13	121.3 (5)
C8—C3—C4	118.8 (5)	C12—C13—C14	116.5 (5)
C8—C3—C2	120.1 (5)	C12—C13—C9	118.1 (5)
C4—C3—C2	121.1 (4)	C14—C13—C9	125.4 (5)
C5—C4—N1	122.2 (5)	C15—C14—C13	121.9 (6)
C5—C4—C3	118.7 (5)	C15—C14—H14	119.0
N1—C4—C3	119.0 (5)	C13—C14—H14	119.0
C6—C5—C4	120.4 (5)	C14—C15—C16	119.4 (6)
C6—C5—H5	119.8	C14—C15—H15	120.3
C4—C5—H5	119.8	C16—C15—H15	120.3
C5—C6—C7	121.1 (5)	C17—C16—C15	120.3 (6)
C5—C6—H6	119.5	C17—C16—H16	119.8
C7—C6—H6	119.5	C15—C16—H16	119.8
C8—C7—C6	119.4 (5)	C16—C17—C12	119.4 (6)
C8—C7—H7	120.3	C16—C17—H17	120.3
C6—C7—H7	120.3	C12—C17—H17	120.3
C7—C8—C3	121.5 (5)
C1—O1—C2—O2	1.4 (10)	C13—C9—C10—C11	−0.2 (9)
C1—O1—C2—C3	−178.0 (6)	C12—O3—C11—O4	−176.1 (6)
O2—C2—C3—C8	−174.9 (7)	C12—O3—C11—C10	4.4 (9)
O1—C2—C3—C8	4.5 (8)	C9—C10—C11—O4	177.8 (7)
O2—C2—C3—C4	3.2 (9)	C9—C10—C11—O3	−2.7 (9)
O1—C2—C3—C4	−177.3 (5)	C11—O3—C12—C17	175.9 (6)
C9—N1—C4—C5	−26.1 (9)	C11—O3—C12—C13	−3.2 (8)
C9—N1—C4—C3	157.9 (6)	C17—C12—C13—C14	−1.4 (9)
C8—C3—C4—C5	4.0 (8)	O3—C12—C13—C14	177.6 (6)
C2—C3—C4—C5	−174.2 (6)	C17—C12—C13—C9	−178.9 (6)
C8—C3—C4—N1	−179.7 (6)	O3—C12—C13—C9	0.1 (8)
C2—C3—C4—N1	2.1 (8)	N1—C9—C13—C12	179.0 (5)
N1—C4—C5—C6	179.8 (6)	C10—C9—C13—C12	1.6 (8)
C3—C4—C5—C6	−4.2 (9)	N1—C9—C13—C14	1.7 (8)
C4—C5—C6—C7	1.4 (10)	C10—C9—C13—C14	−175.7 (5)
C5—C6—C7—C8	1.6 (11)	C12—C13—C14—C15	1.1 (8)
C6—C7—C8—C3	−1.6 (11)	C9—C13—C14—C15	178.4 (6)
C4—C3—C8—C7	−1.2 (10)	C13—C14—C15—C16	0.1 (9)
C2—C3—C8—C7	177.0 (7)	C14—C15—C16—C17	−1.1 (10)
C4—N1—C9—C10	−11.9 (10)	C15—C16—C17—C12	0.8 (10)
C4—N1—C9—C13	171.0 (6)	O3—C12—C17—C16	−178.6 (6)
N1—C9—C10—C11	−177.3 (6)	C13—C12—C17—C16	0.5 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O4^i	0.96	2.52	3.232 (8)	131
C7—H7···O4^ii	0.93	2.47	3.387 (6)	167
N1—H1···O2	0.84 (6)	1.92 (6)	2.631 (6)	141 (5)

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