4-Chloro-2′,3′-dimethoxy­biphen­yl

Vyas, S.M.; Parkin, S.; Robertson, L.W.; Lehmler, H.-J.

doi:10.1107/S1600536806028923

4-Chloro-2′,3′-dimethoxybiphenyl

S. M. Vyas, S. Parkin, L. W. Robertson and H.-J. Lehmler

Molecules of the title compound, C₁₄H₁₃Cl₁O₂, crystallize as centrosymmetric dimers, connected by intermolecular C—H

O hydrogen bonds. The dihedral angle between the benzene rings is 40.05 (6)°.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028923/ci2118sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028923/ci2118Isup2.hkl Contains datablock I

CCDC reference: 620742

checkCIF report

Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.002 Å
R factor = 0.042
wR factor = 0.118
Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

4-Chloro-2',3'-dimethoxybiphenyl top

Crystal data top

C₁₄H₁₃ClO₂	F(000) = 520
M_r = 248.69	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2961 reflections
a = 10.6579 (2) Å	θ = 1.0–27.5°
b = 13.8592 (3) Å	µ = 0.29 mm⁻¹
c = 8.4098 (3) Å	T = 90 K
β = 91.2829 (11)°	Block, colourless
V = 1241.90 (6) Å³	0.22 × 0.20 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2841 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 18 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ω scans at fixed χ = 55°	h = −13→13
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −18→17
T_min = 0.938, T_max = 0.966	l = −10→10
5547 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0658P)² + 0.1233P] where P = (F_o² + 2F_c²)/3
2841 reflections	(Δ/σ)_max = 0.002
156 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

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.

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
Cl1	0.08132 (4)	0.41415 (3)	0.88324 (5)	0.02684 (16)
C1	0.47419 (14)	0.33014 (11)	0.74240 (19)	0.0175 (4)
C1'	0.60066 (15)	0.29805 (12)	0.69207 (18)	0.0175 (4)
C2'	0.68983 (14)	0.36276 (12)	0.63629 (18)	0.0166 (4)
C2	0.41610 (15)	0.28512 (12)	0.86933 (19)	0.0197 (4)
H2	0.4601	0.2363	0.9270	0.024*
C3'	0.80447 (15)	0.32948 (12)	0.57751 (19)	0.0190 (4)
C3	0.29605 (15)	0.30963 (12)	0.91343 (19)	0.0214 (4)
H3	0.2580	0.2784	1.0006	0.026*
C4	0.23219 (14)	0.38050 (13)	0.8284 (2)	0.0191 (4)
C4'	0.83081 (15)	0.23188 (13)	0.5771 (2)	0.0230 (4)
H4'	0.9079	0.2090	0.5368	0.028*
C5	0.28610 (15)	0.42613 (12)	0.70002 (19)	0.0185 (4)
H5	0.2409	0.4740	0.6416	0.022*
C5'	0.74369 (16)	0.16743 (13)	0.6363 (2)	0.0236 (4)
H5'	0.7625	0.1004	0.6382	0.028*
C6	0.40670 (15)	0.40098 (12)	0.65821 (19)	0.0172 (4)
H6	0.4443	0.4324	0.5709	0.021*
C6'	0.63028 (15)	0.19911 (12)	0.6925 (2)	0.0213 (4)
H6'	0.5717	0.1538	0.7317	0.026*
O1'	0.66675 (10)	0.46090 (8)	0.63197 (13)	0.0190 (3)
C7'	0.70634 (18)	0.50970 (14)	0.7740 (2)	0.0312 (5)
H7A'	0.6574	0.4863	0.8635	0.047*
H7B'	0.6931	0.5793	0.7610	0.047*
H7C'	0.7956	0.4970	0.7951	0.047*
O2'	0.88284 (10)	0.39978 (8)	0.52168 (14)	0.0220 (3)
C8'	0.99806 (16)	0.36793 (14)	0.4557 (2)	0.0277 (4)
H8A'	1.0483	0.3345	0.5377	0.042*
H8B'	1.0448	0.4238	0.4170	0.042*
H8C'	0.9801	0.3237	0.3671	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0203 (2)	0.0293 (3)	0.0313 (3)	−0.00044 (17)	0.00823 (18)	−0.00020 (19)
C1	0.0195 (8)	0.0166 (9)	0.0162 (8)	−0.0018 (6)	−0.0014 (6)	−0.0016 (7)
C1'	0.0195 (8)	0.0199 (9)	0.0129 (8)	0.0016 (7)	−0.0022 (6)	0.0006 (7)
C2'	0.0204 (8)	0.0142 (8)	0.0150 (8)	0.0018 (6)	−0.0031 (6)	0.0004 (7)
C2	0.0240 (8)	0.0182 (9)	0.0168 (8)	−0.0004 (7)	−0.0029 (7)	0.0020 (7)
C3'	0.0183 (8)	0.0213 (9)	0.0173 (8)	0.0004 (7)	−0.0020 (6)	0.0025 (7)
C3	0.0250 (9)	0.0230 (9)	0.0163 (8)	−0.0058 (7)	0.0024 (7)	0.0018 (7)
C4	0.0181 (8)	0.0200 (9)	0.0193 (8)	−0.0020 (7)	0.0032 (7)	−0.0032 (7)
C4'	0.0206 (9)	0.0247 (10)	0.0237 (9)	0.0054 (7)	−0.0002 (7)	−0.0001 (8)
C5	0.0200 (8)	0.0155 (9)	0.0199 (9)	0.0002 (6)	−0.0006 (7)	−0.0011 (7)
C5'	0.0272 (9)	0.0167 (9)	0.0265 (10)	0.0044 (7)	−0.0035 (8)	−0.0008 (7)
C6	0.0200 (8)	0.0165 (9)	0.0152 (8)	−0.0022 (6)	0.0007 (6)	−0.0002 (7)
C6'	0.0221 (9)	0.0186 (9)	0.0232 (9)	−0.0019 (7)	−0.0015 (7)	0.0011 (7)
O1'	0.0227 (6)	0.0151 (6)	0.0193 (6)	0.0012 (5)	0.0001 (5)	0.0004 (5)
C7'	0.0440 (11)	0.0225 (10)	0.0268 (10)	−0.0010 (8)	−0.0064 (8)	−0.0067 (8)
O2'	0.0175 (6)	0.0214 (7)	0.0274 (7)	0.0005 (5)	0.0042 (5)	0.0026 (5)
C8'	0.0199 (9)	0.0308 (11)	0.0327 (11)	0.0015 (8)	0.0051 (8)	−0.0025 (9)

Geometric parameters (Å, º) top

Cl1—C4	1.7460 (16)	C4'—H4'	0.95
C1—C2	1.393 (2)	C5—C6	1.385 (2)
C1—C6	1.400 (2)	C5—H5	0.95
C1—C1'	1.490 (2)	C5'—C6'	1.379 (2)
C1'—C2'	1.395 (2)	C5'—H5'	0.95
C1'—C6'	1.407 (2)	C6—H6	0.95
C2'—O1'	1.3826 (19)	C6'—H6'	0.95
C2'—C3'	1.406 (2)	O1'—C7'	1.4285 (19)
C2—C3	1.382 (2)	C7'—H7A'	0.98
C2—H2	0.95	C7'—H7B'	0.98
C3'—O2'	1.3729 (19)	C7'—H7C'	0.98
C3'—C4'	1.382 (2)	O2'—C8'	1.429 (2)
C3—C4	1.385 (2)	C8'—H8A'	0.98
C3—H3	0.95	C8'—H8B'	0.98
C4—C5	1.387 (2)	C8'—H8C'	0.98
C4'—C5'	1.389 (2)

C2—C1—C6	118.00 (15)	C6—C5—H5	120.5
C2—C1—C1'	120.28 (15)	C4—C5—H5	120.5
C6—C1—C1'	121.58 (14)	C6'—C5'—C4'	121.07 (16)
C2'—C1'—C6'	118.21 (15)	C6'—C5'—H5'	119.5
C2'—C1'—C1	122.07 (15)	C4'—C5'—H5'	119.5
C6'—C1'—C1	119.64 (15)	C5—C6—C1	121.16 (15)
O1'—C2'—C1'	121.26 (14)	C5—C6—H6	119.4
O1'—C2'—C3'	117.97 (14)	C1—C6—H6	119.4
C1'—C2'—C3'	120.74 (15)	C5'—C6'—C1'	120.51 (16)
C3—C2—C1	121.68 (15)	C5'—C6'—H6'	119.7
C3—C2—H2	119.2	C1'—C6'—H6'	119.7
C1—C2—H2	119.2	C2'—O1'—C7'	113.25 (12)
O2'—C3'—C4'	124.67 (15)	O1'—C7'—H7A'	109.5
O2'—C3'—C2'	115.32 (14)	O1'—C7'—H7B'	109.5
C4'—C3'—C2'	120.01 (15)	H7A'—C7'—H7B'	109.5
C2—C3—C4	118.88 (15)	O1'—C7'—H7C'	109.5
C2—C3—H3	120.6	H7A'—C7'—H7C'	109.5
C4—C3—H3	120.6	H7B'—C7'—H7C'	109.5
C3—C4—C5	121.20 (15)	C3'—O2'—C8'	116.65 (13)
C3—C4—Cl1	119.88 (13)	O2'—C8'—H8A'	109.5
C5—C4—Cl1	118.93 (13)	O2'—C8'—H8B'	109.5
C3'—C4'—C5'	119.43 (16)	H8A'—C8'—H8B'	109.5
C3'—C4'—H4'	120.3	O2'—C8'—H8C'	109.5
C5'—C4'—H4'	120.3	H8A'—C8'—H8C'	109.5
C6—C5—C4	119.08 (16)	H8B'—C8'—H8C'	109.5

C2—C1—C1'—C2'	−144.42 (16)	C2—C3—C4—Cl1	−179.08 (13)
C6—C1—C1'—C2'	40.1 (2)	O2'—C3'—C4'—C5'	−179.71 (15)
C2—C1—C1'—C6'	38.9 (2)	C2'—C3'—C4'—C5'	−0.5 (2)
C6—C1—C1'—C6'	−136.64 (16)	C3—C4—C5—C6	−1.0 (3)
C6'—C1'—C2'—O1'	179.73 (13)	Cl1—C4—C5—C6	178.72 (12)
C1—C1'—C2'—O1'	3.0 (2)	C3'—C4'—C5'—C6'	1.3 (3)
C6'—C1'—C2'—C3'	2.0 (2)	C4—C5—C6—C1	0.5 (2)
C1—C1'—C2'—C3'	−174.77 (14)	C2—C1—C6—C5	0.4 (2)
C6—C1—C2—C3	−0.7 (2)	C1'—C1—C6—C5	175.99 (15)
C1'—C1—C2—C3	−176.43 (15)	C4'—C5'—C6'—C1'	−0.5 (3)
O1'—C2'—C3'—O2'	0.3 (2)	C2'—C1'—C6'—C5'	−1.2 (2)
C1'—C2'—C3'—O2'	178.12 (14)	C1—C1'—C6'—C5'	175.66 (14)
O1'—C2'—C3'—C4'	−179.00 (14)	C1'—C2'—O1'—C7'	90.65 (18)
C1'—C2'—C3'—C4'	−1.2 (2)	C3'—C2'—O1'—C7'	−91.52 (17)
C1—C2—C3—C4	0.3 (3)	C4'—C3'—O2'—C8'	1.5 (2)
C2—C3—C4—C5	0.6 (3)	C2'—C3'—O2'—C8'	−177.73 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2′ⁱ	0.95	2.57	3.520 (2)	179
C6—H6···O1′	0.95	2.45	2.906 (2)	110
C6—H6···O1′ⁱ	0.95	2.53	3.185 (2)	126

Symmetry code: (i) −x+1, −y+1, −z+1.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

4-Chloro-2′,3′-dimethoxy­biphen­yl

Supporting information

Key indicators

checkCIF/PLATON results

4-Chloro-2′,3′-dimethoxybiphenyl