Crystal structure of 7,8-di­chloro-4-oxo-4H-chromene-3-carbaldehyde

Ishikawa, Y.

doi:10.1107/S205698901501275X

Crystal structure of 7,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde

In the crystal of this dichlorinated 3-formylchromone derivative, molecules are linked through stacking interactions, C—H

O hydrogen bonds and short C

O contacts. Halogen bonds between the formyl O and Cl atoms and type II halogen–halogen contacts between the Cl atoms are also formed.

Keywords: crystal structure; π–π stacking; hydrogen bond; halogen bond; halogen–halogen interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901501275X/zl2631sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901501275X/zl2631Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901501275X/zl2631Isup3.cml Supplementary material

CCDC reference: 1410048

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.025
wR factor = 0.057
Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT481_ALERT_4_B Long D...A H-Bond Reported C6     ..  O3      ..       4.69 Ang.
PLAT481_ALERT_4_B Long D...A H-Bond Reported C7     ..  CL1     ..       5.23 Ang.
PLAT482_ALERT_4_B Small D-H..A Angle Rep for C6     ..  CL2     ..      88.74 Degree
PLAT776_ALERT_1_B Suspect D-H Dist in CIF:   C6     --  CL1     ..       1.72 Ang.
PLAT776_ALERT_1_B Suspect D-H Dist in CIF:   C6     --  CL1     ..       1.72 Ang.
PLAT776_ALERT_1_B Suspect D-H Dist in CIF:   C7     --  CL2     ..       1.72 Ang.
PLAT915_ALERT_3_B Low Friedel Pair Coverage ......................         17 %

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0041 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported CL1    ..  CL2     ..       3.52 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported CL2    ..  CL1     ..       3.52 Ang.

Alert level G
PLAT431_ALERT_2_G Short Inter HL..A  Contact Cl1    ..  O3      ..       2.98 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2     ..  C1      ..       2.84 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

7,8-Dichloro-4-oxo-4H-chromene-3-carbaldehyde top

Crystal data top

C₁₀H₄Cl₂O₃	F(000) = 488.00
M_r = 243.05	D_x = 1.728 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 22 reflections
a = 23.091 (7) Å	θ = 15.8–17.3°
b = 3.7704 (18) Å	µ = 0.67 mm⁻¹
c = 10.729 (5) Å	T = 100 K
V = 934.1 (7) Å³	Plate, yellow
Z = 4	0.41 × 0.12 × 0.05 mm

Data collection top

Rigaku AFC–7R diffractometer	θ_max = 27.5°
ω scans	h = 0→29
1571 measured reflections	k = −4→2
1291 independent reflections	l = −7→13
1155 reflections with F² > 2.0σ(F²)	3 standard reflections every 150 reflections
R_int = 0.015	intensity decay: 1.1%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0252P)² + 0.2201P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1291 reflections	Δρ_max = 0.24 e Å⁻³
136 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 169 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (8)
Secondary atom site location: difference Fourier map

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.02754 (3)	0.3441 (2)	0.16617 (7)	0.02008 (17)
Cl2	0.05650 (3)	−0.0003 (3)	−0.03533 (8)	0.01821 (16)
O1	0.17307 (8)	−0.0690 (6)	0.04845 (18)	0.0137 (5)
O2	0.24923 (9)	0.3154 (5)	0.36500 (17)	0.0179 (5)
O3	0.34477 (9)	−0.3040 (6)	0.12579 (19)	0.0254 (6)
C1	0.22935 (12)	−0.1270 (8)	0.0740 (3)	0.0136 (7)
C2	0.25652 (12)	−0.0155 (7)	0.1782 (3)	0.0140 (6)
C3	0.22568 (13)	0.1862 (9)	0.2724 (3)	0.0149 (7)
C4	0.12566 (13)	0.3790 (8)	0.3362 (3)	0.0156 (7)
C5	0.06756 (13)	0.4108 (8)	0.3106 (3)	0.0169 (7)
C6	0.04536 (12)	0.2967 (8)	0.1961 (3)	0.0156 (7)
C7	0.08124 (12)	0.1435 (8)	0.1075 (3)	0.0132 (7)
C8	0.16288 (12)	0.2231 (8)	0.2485 (3)	0.0116 (7)
C9	0.13996 (12)	0.1023 (8)	0.1362 (3)	0.0127 (7)
C10	0.31843 (13)	−0.1099 (9)	0.1950 (3)	0.0195 (7)
H1	0.2515	−0.2554	0.0145	0.0163*
H2	0.1406	0.4626	0.4133	0.0187*
H3	0.0423	0.5109	0.3710	0.0203*
H4	0.3385	−0.0119	0.2642	0.0233*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0144 (3)	0.0234 (4)	0.0224 (4)	0.0021 (3)	0.0007 (4)	0.0024 (4)
Cl2	0.0181 (3)	0.0216 (4)	0.0149 (3)	−0.0005 (4)	−0.0043 (4)	−0.0019 (4)
O1	0.0147 (10)	0.0162 (12)	0.0102 (10)	0.0015 (9)	−0.0001 (9)	−0.0031 (9)
O2	0.0218 (10)	0.0199 (11)	0.0122 (11)	−0.0014 (10)	−0.0039 (10)	−0.0028 (11)
O3	0.0199 (12)	0.0330 (14)	0.0233 (13)	0.0064 (11)	−0.0001 (9)	−0.0089 (12)
C1	0.0154 (13)	0.0113 (16)	0.0140 (15)	0.0000 (12)	0.0013 (13)	0.0014 (13)
C2	0.0152 (14)	0.0118 (14)	0.0148 (15)	0.0014 (11)	0.0005 (13)	0.0027 (16)
C3	0.0214 (15)	0.0128 (16)	0.0106 (14)	−0.0016 (13)	−0.0019 (13)	0.0040 (14)
C4	0.0224 (15)	0.0113 (16)	0.0130 (16)	−0.0017 (13)	0.0003 (13)	−0.0023 (13)
C5	0.0209 (15)	0.0161 (18)	0.0137 (15)	−0.0012 (14)	0.0064 (13)	−0.0008 (13)
C6	0.0148 (13)	0.0111 (15)	0.0208 (18)	0.0000 (12)	0.0011 (12)	0.0024 (14)
C7	0.0152 (14)	0.0106 (15)	0.0139 (15)	−0.0045 (13)	−0.0033 (12)	0.0026 (13)
C8	0.0149 (14)	0.0112 (16)	0.0087 (14)	−0.0025 (12)	−0.0002 (12)	−0.0002 (12)
C9	0.0193 (14)	0.0093 (14)	0.0095 (14)	0.0016 (12)	0.0030 (12)	0.0016 (12)
C10	0.0209 (15)	0.0208 (17)	0.0166 (16)	0.0003 (14)	0.0012 (13)	−0.0017 (14)

Geometric parameters (Å, º) top

Cl1—C6	1.723 (3)	C4—C5	1.375 (5)
Cl2—C7	1.723 (3)	C4—C8	1.403 (4)
O1—C1	1.346 (4)	C5—C6	1.399 (5)
O1—C9	1.374 (4)	C6—C7	1.387 (4)
O2—C3	1.233 (4)	C7—C9	1.399 (4)
O3—C10	1.207 (4)	C8—C9	1.393 (4)
C1—C2	1.349 (5)	C1—H1	0.950
C2—C3	1.452 (4)	C4—H2	0.950
C2—C10	1.484 (5)	C5—H3	0.950
C3—C8	1.479 (4)	C10—H4	0.950

Cl1···Cl2	3.1821 (13)	Cl1···H3	2.7981
Cl2···O1	2.850 (3)	O2···H2	2.6203
O1···C3	2.860 (4)	O2···H4	2.6344
O2···C1	3.570 (4)	O3···H1	2.4697
O2···C4	2.880 (4)	C1···H4	3.2719
O2···C10	2.907 (4)	C3···H1	3.2841
O3···C1	2.803 (4)	C3···H2	2.6882
C1···C7	3.587 (4)	C3···H4	2.7113
C1···C8	2.758 (5)	C6···H2	3.2648
C2···C9	2.765 (4)	C7···H3	3.2742
C4···C7	2.803 (4)	C8···H3	3.2642
C5···C9	2.766 (4)	C9···H1	3.1865
C6···C8	2.785 (4)	C9···H2	3.2686
Cl1···Cl2ⁱ	3.5191 (17)	C10···H1	2.5378
Cl1···O3ⁱⁱ	2.984 (3)	H1···H4	3.4723
Cl2···Cl1ⁱⁱⁱ	3.5191 (17)	H2···H3	2.3217
O1···O2^iv	3.533 (3)	Cl1···H3^xi	3.2315
O1···O2^v	3.032 (3)	Cl1···H4ⁱⁱ	3.4992
O1···C8^vi	3.434 (4)	Cl2···H3ⁱⁱⁱ	3.1499
O1···C9^vi	3.352 (4)	Cl2···H3^xi	3.1018
O2···O1^vii	3.032 (3)	Cl2···H4^v	3.2415
O2···O1^viii	3.533 (3)	O1···H1^ix	3.5807
O2···C1^vii	2.838 (4)	O1···H4^v	3.0689
O2···C1^viii	3.113 (4)	O2···H1^vii	2.6840
O2···C2^ix	3.227 (4)	O2···H1^viii	2.2789
O2···C2^vii	3.586 (4)	O2···H4^ix	3.4425
O2···C3^ix	3.473 (4)	O3···H2^iv	2.4674
O2···C10^ix	3.252 (4)	O3···H4^vi	3.0577
O3···Cl1^x	2.984 (3)	C1···H1^ix	3.3865
O3···C2^vi	3.415 (4)	C2···H1^ix	3.3630
O3···C4^iv	3.398 (4)	C3···H1^ix	3.5280
O3···C10^vi	3.186 (5)	C3···H1^vii	3.1298
C1···O2^iv	3.113 (4)	C3···H1^viii	3.3849
C1···O2^v	2.838 (4)	C4···H2^vi	3.5694
C1···C2^vi	3.587 (5)	C5···H3^vi	3.5033
C1···C3^vi	3.354 (5)	C6···H3^vi	3.5082
C1···C3^v	3.597 (5)	C8···H2^vi	3.4070
C1···C8^vi	3.445 (5)	C10···H2^iv	3.5538
C2···O2^vi	3.227 (4)	C10···H4^vi	3.5117
C2···O2^v	3.586 (4)	H1···O1^vi	3.5807
C2···O3^ix	3.415 (4)	H1···O2^iv	2.2789
C2···C1^ix	3.587 (5)	H1···O2^v	2.6840
C2···C3^vi	3.254 (5)	H1···C1^vi	3.3865
C3···O2^vi	3.473 (4)	H1···C2^vi	3.3630
C3···C1^ix	3.354 (5)	H1···C3^vi	3.5280
C3···C1^vii	3.597 (5)	H1···C3^iv	3.3849
C3···C2^ix	3.254 (5)	H1···C3^v	3.1298
C3···C10^ix	3.510 (5)	H1···H2^iv	2.9187
C4···O3^viii	3.398 (4)	H1···H4^v	3.5172
C4···C8^ix	3.428 (5)	H2···O3^viii	2.4674
C4···C9^ix	3.486 (4)	H2···C4^ix	3.5694
C5···C6^ix	3.596 (5)	H2···C8^ix	3.4070
C5···C7^ix	3.532 (5)	H2···C10^viii	3.5538
C6···C5^vi	3.596 (5)	H2···H1^viii	2.9187
C6···C7^ix	3.432 (5)	H3···Cl1^xii	3.2315
C7···C5^vi	3.532 (5)	H3···Cl2ⁱ	3.1499
C7···C6^vi	3.432 (5)	H3···Cl2^xii	3.1018
C8···O1^ix	3.434 (4)	H3···C5^ix	3.5033
C8···C1^ix	3.445 (5)	H3···C6^ix	3.5082
C8···C4^vi	3.428 (5)	H4···Cl1^x	3.4992
C8···C9^ix	3.567 (5)	H4···Cl2^vii	3.2415
C9···O1^ix	3.352 (4)	H4···O1^vii	3.0689
C9···C4^vi	3.486 (4)	H4···O2^vi	3.4425
C9···C8^vi	3.567 (5)	H4···O3^ix	3.0577
C10···O2^vi	3.252 (4)	H4···C10^ix	3.5117
C10···O3^ix	3.186 (5)	H4···H1^vii	3.5172
C10···C3^vi	3.510 (5)

C1—O1—C9	118.3 (3)	C3—C8—C4	121.6 (3)
O1—C1—C2	124.5 (3)	C3—C8—C9	119.5 (3)
C1—C2—C3	120.8 (3)	C4—C8—C9	119.0 (3)
C1—C2—C10	118.3 (3)	O1—C9—C7	116.2 (3)
C3—C2—C10	120.9 (3)	O1—C9—C8	122.3 (3)
O2—C3—C2	123.5 (3)	C7—C9—C8	121.5 (3)
O2—C3—C8	122.4 (3)	O3—C10—C2	123.8 (3)
C2—C3—C8	114.2 (3)	O1—C1—H1	117.736
C5—C4—C8	120.0 (3)	C2—C1—H1	117.719
C4—C5—C6	120.4 (3)	C5—C4—H2	119.983
Cl1—C6—C5	119.3 (3)	C8—C4—H2	119.980
Cl1—C6—C7	120.0 (3)	C4—C5—H3	119.801
C5—C6—C7	120.7 (3)	C6—C5—H3	119.790
Cl2—C7—C6	122.8 (3)	O3—C10—H4	118.100
Cl2—C7—C9	118.8 (2)	C2—C10—H4	118.125
C6—C7—C9	118.3 (3)

C1—O1—C9—C7	−177.5 (3)	C8—C4—C5—C6	−1.6 (5)
C1—O1—C9—C8	1.3 (4)	C8—C4—C5—H3	178.4
C9—O1—C1—C2	−2.9 (4)	H2—C4—C5—C6	178.4
C9—O1—C1—H1	177.1	H2—C4—C5—H3	−1.6
O1—C1—C2—C3	−0.8 (5)	H2—C4—C8—C3	−0.4
O1—C1—C2—C10	178.1 (3)	H2—C4—C8—C9	180.0
H1—C1—C2—C3	179.2	C4—C5—C6—Cl1	−179.4 (3)
H1—C1—C2—C10	−1.9	C4—C5—C6—C7	1.3 (5)
C1—C2—C3—O2	−174.8 (3)	H3—C5—C6—Cl1	0.6
C1—C2—C3—C8	5.5 (4)	H3—C5—C6—C7	−178.7
C1—C2—C10—O3	−6.0 (5)	Cl1—C6—C7—Cl2	1.0 (4)
C1—C2—C10—H4	173.9	Cl1—C6—C7—C9	−178.62 (18)
C3—C2—C10—O3	172.8 (3)	C5—C6—C7—Cl2	−179.7 (3)
C3—C2—C10—H4	−7.2	C5—C6—C7—C9	0.7 (5)
C10—C2—C3—O2	6.3 (5)	Cl2—C7—C9—O1	−3.2 (4)
C10—C2—C3—C8	−173.4 (3)	Cl2—C7—C9—C8	178.01 (18)
O2—C3—C8—C4	−6.1 (5)	C6—C7—C9—O1	176.4 (3)
O2—C3—C8—C9	173.5 (3)	C6—C7—C9—C8	−2.4 (4)
C2—C3—C8—C4	173.6 (3)	C3—C8—C9—O1	3.7 (4)
C2—C3—C8—C9	−6.8 (4)	C3—C8—C9—C7	−177.6 (3)
C5—C4—C8—C3	179.6 (3)	C4—C8—C9—O1	−176.7 (3)
C5—C4—C8—C9	−0.0 (4)	C4—C8—C9—C7	2.0 (4)

Symmetry codes: (i) −x, −y, z+1/2; (ii) x−1/2, −y, z; (iii) −x, −y, z−1/2; (iv) −x+1/2, y−1, z−1/2; (v) −x+1/2, y, z−1/2; (vi) x, y−1, z; (vii) −x+1/2, y, z+1/2; (viii) −x+1/2, y+1, z+1/2; (ix) x, y+1, z; (x) x+1/2, −y, z; (xi) −x, −y+1, z−1/2; (xii) −x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2^iv	0.95	2.28	3.113 (4)	146 (1)
C4—H2···O3^viii	0.95	2.47	3.398 (4)	167 (1)
C6—Cl1···O3ⁱⁱ	1.72 (1)	2.98 (1)	4.693 (4)	171 (1)
C10—O3···Cl1^x	1.21 (1)	2.98 (1)	3.678 (4)	116 (1)
C6—Cl1···Cl2ⁱ	1.72 (1)	3.52 (1)	3.884 (4)	89 (1)
C7—Cl2···Cl1ⁱⁱⁱ	1.72 (1)	3.52 (1)	5.229 (4)	171 (1)

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

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Crystal structure of 7,8-di­chloro-4-oxo-4H-chromene-3-carbaldehyde

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of 7,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde