Crystal structure of 2-oxo-2H-chromen-3-yl 4-chloro­benzoate and Hirshfeld surface analysis

In the title compound, C₁₆H₉ClO₄, the dihedral angle between the coumarin ring system [maximum deviation = 0.023 (1) Å] and the benzene ring is 73.95 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.106
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         24 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Oxo-2H-chromen-3-yl 4-chlorobenzoate

Crystal data

C16H9ClO4	Z = 2
Mr = 300.68	F(000) = 308
Triclinic, P1	Dx = 1.523 Mg m^−3
Hall symbol: -P 1	Melting point: 478 K
a = 6.7866 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.1789 (3) Å	Cell parameters from 3886 reflections
c = 14.0981 (5) Å	θ = 6.3–69.1°
α = 94.098 (3)°	µ = 2.72 mm^−1
β = 93.461 (4)°	T = 293 K
γ = 106.154 (4)°	Prism, colourless
V = 655.75 (5) Å^3	0.12 × 0.12 × 0.08 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2409 independent reflections
Radiation source: fine-focus sealed tube	2109 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 5.3048 pixels mm^-1	θmax = 69.1°, θmin = 6.3°
ω scan	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −8→8
Tmin = 0.737, Tmax = 0.812	l = −17→16
7634 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.1948P] where P = (Fo^2 + 2Fc^2)/3
2409 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

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.

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 > 2sigma(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
C1	0.1899 (3)	0.0796 (2)	0.35706 (12)	0.0446 (4)
C2	0.3804 (3)	0.0653 (2)	0.31891 (11)	0.0422 (4)
C3	0.5634 (3)	0.1322 (2)	0.36885 (11)	0.0414 (4)
H3	0.6815	0.1187	0.3424	0.050*
C4	0.5771 (2)	0.2250 (2)	0.46354 (11)	0.0384 (3)
C5	0.7616 (3)	0.3026 (2)	0.52035 (13)	0.0475 (4)
H5	0.8848	0.2943	0.4975	0.057*
C6	0.7618 (3)	0.3918 (3)	0.61044 (14)	0.0549 (5)
H6	0.8856	0.4451	0.6475	0.066*
C7	0.5794 (3)	0.4022 (3)	0.64594 (12)	0.0534 (5)
H7	0.5813	0.4628	0.7067	0.064*
C8	0.3938 (3)	0.3229 (2)	0.59161 (12)	0.0474 (4)
H8	0.2705	0.3270	0.6158	0.057*
C9	0.3956 (2)	0.2379 (2)	0.50103 (11)	0.0390 (3)
C10	0.3047 (3)	0.0312 (3)	0.15135 (12)	0.0459 (4)
C11	0.2730 (2)	−0.1155 (3)	0.06844 (12)	0.0458 (4)
C16	0.2973 (3)	−0.2994 (3)	0.07788 (13)	0.0525 (4)
H16	0.3335	−0.3326	0.1377	0.063*
C15	0.2683 (3)	−0.4333 (3)	−0.00072 (14)	0.0599 (5)
H15	0.2832	−0.5568	0.0058	0.072*
C14	0.2170 (3)	−0.3809 (4)	−0.08894 (14)	0.0626 (6)
C13	0.1904 (3)	−0.1999 (4)	−0.10068 (13)	0.0649 (6)
H13	0.1534	−0.1680	−0.1607	0.078*
C12	0.2200 (3)	−0.0667 (3)	−0.02135 (13)	0.0555 (5)
H12	0.2042	0.0564	−0.0282	0.067*
Cl1	0.18104 (10)	−0.55203 (13)	−0.18674 (4)	0.0951 (3)
O1	0.20802 (17)	0.16486 (17)	0.44814 (8)	0.0444 (3)
O2	0.0204 (2)	0.0211 (2)	0.31579 (10)	0.0637 (4)
O3	0.3603 (2)	−0.04346 (18)	0.23221 (8)	0.0516 (3)
O4	0.2900 (2)	0.1930 (2)	0.15125 (10)	0.0592 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0428 (9)	0.0444 (8)	0.0465 (9)	0.0127 (7)	0.0018 (7)	0.0042 (7)
C2	0.0515 (10)	0.0402 (8)	0.0374 (8)	0.0177 (7)	0.0038 (7)	0.0026 (6)
C3	0.0424 (9)	0.0431 (8)	0.0433 (8)	0.0176 (7)	0.0101 (7)	0.0082 (7)
C4	0.0411 (8)	0.0336 (7)	0.0420 (8)	0.0117 (6)	0.0044 (6)	0.0066 (6)
C5	0.0426 (9)	0.0461 (9)	0.0549 (10)	0.0139 (7)	0.0001 (7)	0.0097 (7)
C6	0.0597 (11)	0.0467 (9)	0.0538 (10)	0.0117 (8)	−0.0144 (8)	0.0049 (8)
C7	0.0801 (13)	0.0438 (9)	0.0386 (8)	0.0230 (9)	−0.0015 (8)	0.0018 (7)
C8	0.0601 (11)	0.0458 (9)	0.0420 (8)	0.0230 (8)	0.0084 (7)	0.0057 (7)
C9	0.0417 (8)	0.0346 (7)	0.0428 (8)	0.0134 (6)	0.0045 (6)	0.0069 (6)
C10	0.0369 (9)	0.0587 (10)	0.0442 (9)	0.0156 (7)	0.0051 (7)	0.0082 (7)
C11	0.0341 (8)	0.0648 (11)	0.0388 (8)	0.0140 (7)	0.0044 (6)	0.0048 (7)
C16	0.0515 (10)	0.0651 (11)	0.0407 (9)	0.0181 (8)	0.0000 (7)	0.0006 (8)
C15	0.0541 (11)	0.0709 (12)	0.0519 (10)	0.0169 (9)	0.0015 (8)	−0.0073 (9)
C14	0.0401 (10)	0.0978 (16)	0.0434 (10)	0.0137 (10)	0.0043 (7)	−0.0134 (10)
C13	0.0437 (10)	0.1146 (19)	0.0370 (9)	0.0235 (11)	0.0029 (7)	0.0066 (10)
C12	0.0432 (10)	0.0826 (13)	0.0446 (9)	0.0217 (9)	0.0061 (7)	0.0141 (9)
Cl1	0.0754 (4)	0.1412 (6)	0.0550 (3)	0.0214 (4)	0.0009 (3)	−0.0395 (4)
O1	0.0383 (6)	0.0504 (6)	0.0464 (6)	0.0160 (5)	0.0069 (5)	0.0012 (5)
O2	0.0439 (7)	0.0792 (9)	0.0619 (8)	0.0120 (6)	−0.0056 (6)	−0.0029 (7)
O3	0.0686 (8)	0.0544 (7)	0.0369 (6)	0.0280 (6)	0.0000 (5)	−0.0007 (5)
O4	0.0689 (9)	0.0586 (8)	0.0561 (8)	0.0273 (7)	0.0046 (6)	0.0092 (6)

Geometric parameters (Å, º)

C1—O2	1.206 (2)	C8—H8	0.9300
C1—O1	1.366 (2)	C9—O1	1.382 (2)
C1—C2	1.456 (2)	C10—O4	1.193 (2)
C2—C3	1.335 (2)	C10—O3	1.370 (2)
C2—O3	1.3809 (19)	C10—C11	1.479 (2)
C3—C4	1.435 (2)	C11—C16	1.390 (3)
C3—H3	0.9300	C11—C12	1.390 (2)
C4—C9	1.393 (2)	C16—C15	1.381 (3)
C4—C5	1.395 (2)	C16—H16	0.9300
C5—C6	1.380 (3)	C15—C14	1.377 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.382 (3)	C14—C13	1.381 (4)
C6—H6	0.9300	C14—Cl1	1.738 (2)
C7—C8	1.385 (3)	C13—C12	1.385 (3)
C7—H7	0.9300	C13—H13	0.9300
C8—C9	1.378 (2)	C12—H12	0.9300
O2—C1—O1	118.19 (16)	C8—C9—C4	122.08 (16)
O2—C1—C2	125.73 (17)	O1—C9—C4	120.91 (14)
O1—C1—C2	116.07 (14)	O4—C10—O3	122.83 (17)
C3—C2—O3	120.59 (15)	O4—C10—C11	127.29 (16)
C3—C2—C1	122.67 (15)	O3—C10—C11	109.86 (15)
O3—C2—C1	116.26 (15)	C16—C11—C12	119.31 (18)
C2—C3—C4	119.71 (15)	C16—C11—C10	121.73 (16)
C2—C3—H3	120.1	C12—C11—C10	118.96 (18)
C4—C3—H3	120.1	C15—C16—C11	120.64 (18)
C9—C4—C5	118.11 (15)	C15—C16—H16	119.7
C9—C4—C3	118.07 (15)	C11—C16—H16	119.7
C5—C4—C3	123.81 (15)	C14—C15—C16	118.9 (2)
C6—C5—C4	120.22 (17)	C14—C15—H15	120.5
C6—C5—H5	119.9	C16—C15—H15	120.5
C4—C5—H5	119.9	C15—C14—C13	121.89 (19)
C5—C6—C7	120.47 (17)	C15—C14—Cl1	118.0 (2)
C5—C6—H6	119.8	C13—C14—Cl1	120.05 (16)
C7—C6—H6	119.8	C14—C13—C12	118.72 (18)
C6—C7—C8	120.40 (17)	C14—C13—H13	120.6
C6—C7—H7	119.8	C12—C13—H13	120.6
C8—C7—H7	119.8	C13—C12—C11	120.5 (2)
C9—C8—C7	118.70 (17)	C13—C12—H12	119.7
C9—C8—H8	120.6	C11—C12—H12	119.7
C7—C8—H8	120.6	C1—O1—C9	122.54 (13)
C8—C9—O1	117.01 (15)	C10—O3—C2	118.78 (14)
O2—C1—C2—C3	−179.51 (17)	O4—C10—C11—C12	0.0 (3)
O1—C1—C2—C3	−0.5 (2)	O3—C10—C11—C12	−178.60 (15)
O2—C1—C2—O3	−7.4 (3)	C12—C11—C16—C15	−0.3 (3)
O1—C1—C2—O3	171.59 (13)	C10—C11—C16—C15	−179.53 (16)
O3—C2—C3—C4	−172.69 (13)	C11—C16—C15—C14	0.7 (3)
C1—C2—C3—C4	−0.9 (2)	C16—C15—C14—C13	−1.1 (3)
C2—C3—C4—C9	1.5 (2)	C16—C15—C14—Cl1	−179.94 (15)
C2—C3—C4—C5	−178.72 (15)	C15—C14—C13—C12	1.1 (3)
C9—C4—C5—C6	−1.0 (2)	Cl1—C14—C13—C12	179.94 (14)
C3—C4—C5—C6	179.23 (15)	C14—C13—C12—C11	−0.7 (3)
C4—C5—C6—C7	1.1 (3)	C16—C11—C12—C13	0.3 (3)
C5—C6—C7—C8	0.2 (3)	C10—C11—C12—C13	179.57 (16)
C6—C7—C8—C9	−1.5 (3)	O2—C1—O1—C9	−179.48 (15)
C7—C8—C9—O1	−178.39 (14)	C2—C1—O1—C9	1.4 (2)
C7—C8—C9—C4	1.6 (2)	C8—C9—O1—C1	179.09 (14)
C5—C4—C9—C8	−0.4 (2)	C4—C9—O1—C1	−0.9 (2)
C3—C4—C9—C8	179.42 (14)	O4—C10—O3—C2	6.6 (3)
C5—C4—C9—O1	179.60 (13)	C11—C10—O3—C2	−174.68 (14)
C3—C4—C9—O1	−0.6 (2)	C3—C2—O3—C10	−115.15 (18)
O4—C10—C11—C16	179.25 (18)	C1—C2—O3—C10	72.60 (19)
O3—C10—C11—C16	0.6 (2)