3-Diethyl-carbamoyl-2',4'-difluoro-biphenyl-4-yl 2,6-dichloro-5-fluoro-pyridine-3-carboxyl-ate.

In the title compound, C(23)H(17)Cl(2)F(3)N(2)O(3), the mol-ecular conformation is significantly strained: atoms O, C(=O) and C attached to the central benzene ring deviate from its plane by 0.118 (2), 0.139 (2) and 0.174 (2) Å, respectively. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into chains along [110]. The crystal packing exhibits short inter-molecular Cl⋯F [2.9840 (16) Å] and Cl⋯Cl [3.2957 (12) Å] contacts.

Related literature

For details of the synthesis, see: Zhong et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C23H17Cl2F3N2O3

M = 497.29

Triclinic,

a = 10.635 (3) Å

b = 10.888 (3) Å

c = 11.310 (3) Å

α = 96.838 (1)°

β = 109.213 (1)°

γ = 116.017 (3)°

V = 1056.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 153 K

0.47 × 0.45 × 0.41 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.848, T max = 0.866

10358 measured reflections

4752 independent reflections

3984 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 1.00

4752 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025354/cv5305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025354/cv5305Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025354/cv5305Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H17Cl2F3N2O3	Z = 2
Mr = 497.29	F(000) = 508
Triclinic, P1	Dx = 1.563 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.635 (3) Å	Cell parameters from 3183 reflections
b = 10.888 (3) Å	θ = 3.2–27.5°
c = 11.310 (3) Å	µ = 0.36 mm−1
α = 96.838 (1)°	T = 153 K
β = 109.213 (1)°	Block, colourless
γ = 116.017 (3)°	0.47 × 0.45 × 0.41 mm
V = 1056.5 (5) Å3

Rigaku AFC10/Saturn724+ diffractometer	4752 independent reflections
Radiation source: Rotating Anode	3984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
phi and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→9
Tmin = 0.848, Tmax = 0.866	l = −14→14
10358 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.563P] where P = (Fo2 + 2Fc2)/3
4752 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	1.02347 (5)	0.66238 (5)	0.52667 (4)	0.03025 (12)
Cl2	1.55188 (5)	1.10870 (5)	0.83855 (4)	0.03247 (12)
F1	0.21518 (11)	0.21751 (10)	0.77572 (10)	0.0272 (2)
F2	−0.13376 (10)	0.31772 (11)	0.86694 (10)	0.0277 (2)
F3	1.40442 (12)	1.12878 (12)	1.01131 (10)	0.0387 (3)
O1	0.86955 (11)	0.70469 (12)	0.83236 (10)	0.0182 (2)
O2	0.79299 (12)	0.66272 (12)	0.61291 (10)	0.0207 (2)
O3	0.80388 (12)	0.93820 (11)	0.80944 (11)	0.0211 (2)
N1	1.27582 (15)	0.88489 (14)	0.69998 (13)	0.0203 (3)
N2	0.61806 (14)	0.82558 (13)	0.59926 (12)	0.0164 (3)
C1	0.17396 (17)	0.31502 (16)	0.80292 (15)	0.0170 (3)
C2	0.03987 (17)	0.26486 (17)	0.82120 (15)	0.0195 (3)
H2	−0.0188	0.1676	0.8171	0.023*
C3	−0.00431 (17)	0.36277 (18)	0.84561 (15)	0.0195 (3)
C4	0.07763 (17)	0.50429 (17)	0.85192 (15)	0.0197 (3)
H4	0.0426	0.5687	0.8672	0.024*
C5	0.21328 (17)	0.55015 (17)	0.83529 (14)	0.0176 (3)
H5	0.2719	0.6480	0.8408	0.021*
C6	0.26640 (16)	0.45728 (16)	0.81069 (14)	0.0148 (3)
C7	0.41797 (16)	0.51242 (15)	0.80320 (13)	0.0144 (3)
C8	0.51496 (17)	0.45898 (16)	0.85426 (14)	0.0161 (3)
H8	0.4797	0.3794	0.8864	0.019*
C9	0.66232 (17)	0.52086 (16)	0.85858 (14)	0.0165 (3)
H9	0.7268	0.4825	0.8915	0.020*
C10	0.71436 (16)	0.63841 (16)	0.81465 (14)	0.0154 (3)
C11	0.62084 (16)	0.69371 (15)	0.76086 (14)	0.0146 (3)
C12	0.47150 (16)	0.62775 (16)	0.75432 (14)	0.0150 (3)
H12	0.4048	0.6622	0.7157	0.018*
C13	0.89366 (17)	0.71843 (16)	0.72222 (15)	0.0160 (3)
C14	1.06198 (17)	0.81361 (16)	0.75919 (15)	0.0157 (3)
C15	1.12842 (17)	0.79897 (16)	0.67455 (15)	0.0175 (3)
C16	1.36315 (17)	0.99312 (17)	0.81058 (16)	0.0207 (3)
C17	1.30851 (18)	1.01633 (17)	0.90099 (16)	0.0231 (3)
C18	1.15754 (18)	0.92607 (17)	0.87740 (16)	0.0204 (3)
H18	1.1194	0.9399	0.9398	0.024*
C19	0.68695 (16)	0.82890 (15)	0.72380 (14)	0.0148 (3)
C20	0.49642 (17)	0.69441 (16)	0.48941 (14)	0.0173 (3)
H20A	0.4784	0.6097	0.5207	0.021*
H20B	0.5316	0.6862	0.4195	0.021*
C21	0.34556 (19)	0.69431 (19)	0.43204 (17)	0.0252 (4)
H21A	0.3094	0.7008	0.5006	0.038*
H21B	0.2675	0.6052	0.3594	0.038*
H21C	0.3624	0.7769	0.3992	0.038*
C22	0.69372 (18)	0.95545 (17)	0.56353 (16)	0.0220 (3)
H22A	0.7312	1.0415	0.6357	0.026*
H22B	0.6174	0.9539	0.4835	0.026*
C23	0.8299 (2)	0.96539 (19)	0.53800 (18)	0.0288 (4)
H23A	0.9051	0.9660	0.6169	0.043*
H23B	0.8794	1.0541	0.5168	0.043*
H23C	0.7923	0.8824	0.4640	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0241 (2)	0.0259 (2)	0.0298 (2)	0.00427 (17)	0.01557 (17)	−0.00399 (17)
Cl2	0.01363 (19)	0.0355 (2)	0.0353 (2)	0.00161 (17)	0.01171 (17)	0.00979 (19)
F1	0.0238 (5)	0.0163 (5)	0.0400 (6)	0.0075 (4)	0.0168 (5)	0.0064 (4)
F2	0.0139 (5)	0.0356 (6)	0.0319 (5)	0.0079 (4)	0.0141 (4)	0.0120 (4)
F3	0.0237 (5)	0.0331 (6)	0.0292 (6)	−0.0039 (5)	0.0099 (5)	−0.0086 (5)
O1	0.0106 (5)	0.0242 (6)	0.0184 (5)	0.0064 (4)	0.0071 (4)	0.0093 (4)
O2	0.0155 (5)	0.0233 (6)	0.0194 (5)	0.0079 (5)	0.0071 (4)	0.0040 (4)
O3	0.0162 (5)	0.0171 (5)	0.0195 (5)	0.0016 (4)	0.0057 (4)	0.0052 (4)
N1	0.0166 (6)	0.0224 (7)	0.0238 (7)	0.0089 (6)	0.0113 (5)	0.0093 (5)
N2	0.0156 (6)	0.0136 (6)	0.0177 (6)	0.0057 (5)	0.0066 (5)	0.0064 (5)
C1	0.0158 (7)	0.0162 (7)	0.0175 (7)	0.0073 (6)	0.0068 (6)	0.0049 (6)
C2	0.0141 (7)	0.0170 (7)	0.0178 (7)	0.0010 (6)	0.0059 (6)	0.0054 (6)
C3	0.0097 (7)	0.0278 (8)	0.0165 (7)	0.0055 (6)	0.0057 (6)	0.0080 (6)
C4	0.0152 (7)	0.0252 (8)	0.0211 (7)	0.0118 (7)	0.0076 (6)	0.0095 (6)
C5	0.0145 (7)	0.0184 (7)	0.0181 (7)	0.0066 (6)	0.0062 (6)	0.0087 (6)
C6	0.0115 (7)	0.0166 (7)	0.0120 (6)	0.0041 (6)	0.0040 (5)	0.0054 (5)
C7	0.0115 (7)	0.0148 (7)	0.0121 (6)	0.0035 (6)	0.0045 (5)	0.0034 (5)
C8	0.0162 (7)	0.0148 (7)	0.0144 (7)	0.0050 (6)	0.0067 (6)	0.0066 (5)
C9	0.0151 (7)	0.0192 (7)	0.0157 (7)	0.0092 (6)	0.0061 (6)	0.0066 (6)
C10	0.0101 (6)	0.0176 (7)	0.0144 (7)	0.0038 (6)	0.0057 (5)	0.0046 (6)
C11	0.0142 (7)	0.0137 (7)	0.0134 (6)	0.0047 (6)	0.0065 (5)	0.0042 (5)
C12	0.0136 (7)	0.0158 (7)	0.0142 (7)	0.0067 (6)	0.0053 (5)	0.0053 (5)
C13	0.0159 (7)	0.0146 (7)	0.0205 (7)	0.0085 (6)	0.0092 (6)	0.0075 (6)
C14	0.0137 (7)	0.0160 (7)	0.0200 (7)	0.0079 (6)	0.0085 (6)	0.0088 (6)
C15	0.0178 (7)	0.0166 (7)	0.0193 (7)	0.0087 (6)	0.0092 (6)	0.0065 (6)
C16	0.0134 (7)	0.0222 (8)	0.0257 (8)	0.0067 (6)	0.0095 (6)	0.0113 (6)
C17	0.0179 (8)	0.0198 (8)	0.0208 (8)	0.0034 (6)	0.0065 (6)	0.0018 (6)
C18	0.0187 (8)	0.0227 (8)	0.0207 (7)	0.0091 (7)	0.0115 (6)	0.0072 (6)
C19	0.0124 (7)	0.0150 (7)	0.0184 (7)	0.0065 (6)	0.0086 (6)	0.0061 (6)
C20	0.0174 (7)	0.0163 (7)	0.0154 (7)	0.0071 (6)	0.0061 (6)	0.0045 (6)
C21	0.0187 (8)	0.0245 (8)	0.0250 (8)	0.0097 (7)	0.0037 (7)	0.0054 (7)
C22	0.0215 (8)	0.0173 (8)	0.0229 (8)	0.0067 (7)	0.0077 (6)	0.0109 (6)
C23	0.0278 (9)	0.0266 (9)	0.0302 (9)	0.0072 (7)	0.0178 (8)	0.0141 (7)

Cl1—C15	1.7255 (16)	C8—C9	1.389 (2)
Cl2—C16	1.7274 (16)	C8—H8	0.9500
F1—C1	1.3540 (18)	C9—C10	1.379 (2)
F2—C3	1.3596 (17)	C9—H9	0.9500
F3—C17	1.3413 (18)	C10—C11	1.391 (2)
O1—C13	1.3641 (18)	C11—C12	1.398 (2)
O1—C10	1.4101 (17)	C11—C19	1.507 (2)
O2—C13	1.1929 (18)	C12—H12	0.9500
O3—C19	1.2391 (18)	C13—C14	1.493 (2)
N1—C16	1.319 (2)	C14—C18	1.394 (2)
N1—C15	1.330 (2)	C14—C15	1.396 (2)
N2—C19	1.3444 (19)	C16—C17	1.380 (2)
N2—C20	1.4682 (19)	C17—C18	1.373 (2)
N2—C22	1.4704 (19)	C18—H18	0.9500
C1—C2	1.383 (2)	C20—C21	1.519 (2)
C1—C6	1.396 (2)	C20—H20A	0.9900
C2—C3	1.374 (2)	C20—H20B	0.9900
C2—H2	0.9500	C21—H21A	0.9800
C3—C4	1.376 (2)	C21—H21B	0.9800
C4—C5	1.391 (2)	C21—H21C	0.9800
C4—H4	0.9500	C22—C23	1.529 (2)
C5—C6	1.399 (2)	C22—H22A	0.9900
C5—H5	0.9500	C22—H22B	0.9900
C6—C7	1.490 (2)	C23—H23A	0.9800
C7—C8	1.397 (2)	C23—H23B	0.9800
C7—C12	1.397 (2)	C23—H23C	0.9800
C13—O1—C10	116.40 (11)	O1—C13—C14	110.21 (12)
C16—N1—C15	117.65 (13)	C18—C14—C15	117.25 (14)
C19—N2—C20	124.77 (13)	C18—C14—C13	120.94 (13)
C19—N2—C22	117.30 (12)	C15—C14—C13	121.72 (14)
C20—N2—C22	116.24 (12)	N1—C15—C14	124.14 (14)
F1—C1—C2	116.52 (13)	N1—C15—Cl1	114.07 (11)
F1—C1—C6	119.33 (13)	C14—C15—Cl1	121.77 (12)
C2—C1—C6	124.15 (15)	N1—C16—C17	122.56 (14)
C3—C2—C1	116.65 (14)	N1—C16—Cl2	117.10 (12)
C3—C2—H2	121.7	C17—C16—Cl2	120.33 (13)
C1—C2—H2	121.7	F3—C17—C18	120.62 (15)
F2—C3—C2	118.14 (14)	F3—C17—C16	119.09 (14)
F2—C3—C4	118.66 (15)	C18—C17—C16	120.29 (15)
C2—C3—C4	123.19 (14)	C17—C18—C14	118.05 (14)
C3—C4—C5	117.96 (15)	C17—C18—H18	121.0
C3—C4—H4	121.0	C14—C18—H18	121.0
C5—C4—H4	121.0	O3—C19—N2	122.80 (14)
C4—C5—C6	122.29 (14)	O3—C19—C11	118.38 (13)
C4—C5—H5	118.9	N2—C19—C11	118.82 (13)
C6—C5—H5	118.9	N2—C20—C21	111.98 (13)
C1—C6—C5	115.73 (14)	N2—C20—H20A	109.2
C1—C6—C7	123.36 (14)	C21—C20—H20A	109.2
C5—C6—C7	120.78 (13)	N2—C20—H20B	109.2
C8—C7—C12	118.48 (13)	C21—C20—H20B	109.2
C8—C7—C6	121.26 (13)	H20A—C20—H20B	107.9
C12—C7—C6	120.05 (13)	C20—C21—H21A	109.5
C9—C8—C7	120.72 (14)	C20—C21—H21B	109.5
C9—C8—H8	119.6	H21A—C21—H21B	109.5
C7—C8—H8	119.6	C20—C21—H21C	109.5
C10—C9—C8	119.46 (14)	H21A—C21—H21C	109.5
C10—C9—H9	120.3	H21B—C21—H21C	109.5
C8—C9—H9	120.3	N2—C22—C23	111.44 (14)
C9—C10—C11	121.79 (13)	N2—C22—H22A	109.3
C9—C10—O1	116.95 (13)	C23—C22—H22A	109.3
C11—C10—O1	121.19 (13)	N2—C22—H22B	109.3
C10—C11—C12	117.89 (13)	C23—C22—H22B	109.3
C10—C11—C19	119.70 (13)	H22A—C22—H22B	108.0
C12—C11—C19	122.16 (13)	C22—C23—H23A	109.5
C7—C12—C11	121.57 (14)	C22—C23—H23B	109.5
C7—C12—H12	119.2	H23A—C23—H23B	109.5
C11—C12—H12	119.2	C22—C23—H23C	109.5
O2—C13—O1	124.03 (14)	H23A—C23—H23C	109.5
O2—C13—C14	125.75 (14)	H23B—C23—H23C	109.5
F1—C1—C2—C3	−178.45 (13)	C10—O1—C13—C14	169.47 (12)
C6—C1—C2—C3	1.5 (2)	O2—C13—C14—C18	147.58 (16)
C1—C2—C3—F2	−178.57 (13)	O1—C13—C14—C18	−31.7 (2)
C1—C2—C3—C4	0.2 (2)	O2—C13—C14—C15	−28.9 (2)
F2—C3—C4—C5	177.39 (13)	O1—C13—C14—C15	151.77 (14)
C2—C3—C4—C5	−1.3 (2)	C16—N1—C15—C14	−2.1 (2)
C3—C4—C5—C6	1.0 (2)	C16—N1—C15—Cl1	179.14 (12)
F1—C1—C6—C5	178.17 (13)	C18—C14—C15—N1	0.1 (2)
C2—C1—C6—C5	−1.7 (2)	C13—C14—C15—N1	176.77 (14)
F1—C1—C6—C7	−6.0 (2)	C18—C14—C15—Cl1	178.85 (12)
C2—C1—C6—C7	174.07 (14)	C13—C14—C15—Cl1	−4.5 (2)
C4—C5—C6—C1	0.4 (2)	C15—N1—C16—C17	2.3 (2)
C4—C5—C6—C7	−175.48 (13)	C15—N1—C16—Cl2	−177.03 (12)
C1—C6—C7—C8	−33.6 (2)	N1—C16—C17—F3	179.96 (15)
C5—C6—C7—C8	142.01 (15)	Cl2—C16—C17—F3	−0.7 (2)
C1—C6—C7—C12	151.76 (14)	N1—C16—C17—C18	−0.6 (3)
C5—C6—C7—C12	−32.6 (2)	Cl2—C16—C17—C18	178.67 (13)
C12—C7—C8—C9	1.2 (2)	F3—C17—C18—C14	178.05 (15)
C6—C7—C8—C9	−173.54 (13)	C16—C17—C18—C14	−1.3 (3)
C7—C8—C9—C10	1.5 (2)	C15—C14—C18—C17	1.6 (2)
C8—C9—C10—C11	−2.7 (2)	C13—C14—C18—C17	−175.12 (15)
C8—C9—C10—O1	174.41 (12)	C20—N2—C19—O3	169.20 (14)
C13—O1—C10—C9	124.95 (14)	C22—N2—C19—O3	4.6 (2)
C13—O1—C10—C11	−57.97 (18)	C20—N2—C19—C11	−10.0 (2)
C9—C10—C11—C12	1.1 (2)	C22—N2—C19—C11	−174.58 (13)
O1—C10—C11—C12	−175.89 (13)	C10—C11—C19—O3	−55.73 (19)
C9—C10—C11—C19	175.39 (14)	C12—C11—C19—O3	118.36 (16)
O1—C10—C11—C19	−1.6 (2)	C10—C11—C19—N2	123.49 (15)
C8—C7—C12—C11	−2.8 (2)	C12—C11—C19—N2	−62.43 (19)
C6—C7—C12—C11	171.97 (13)	C19—N2—C20—C21	117.76 (16)
C10—C11—C12—C7	1.7 (2)	C22—N2—C20—C21	−77.50 (17)
C19—C11—C12—C7	−172.46 (13)	C19—N2—C22—C23	78.92 (17)
C10—O1—C13—O2	−9.8 (2)	C20—N2—C22—C23	−87.00 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.95	2.35	3.287 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.95	2.35	3.287 (2)	170

Symmetry code: (i) .