(R)-Prop-2-ynyl 2-[4-(5-chloro-3-fluoro­pyridin-2-yl­oxy)phen­oxy]propanoate

Liu, X.-G.; Jia, H.-S.; Chen, Y.-S.; Ma, H.-F.

doi:10.1107/S1600536807021319

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(R)-Prop-2-ynyl 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propanoate

X.-G. Liu, H.-S. Jia, Y.-S. Chen and H.-F. Ma

The asymmetric unit of the title compound, C₁₇H₁₃ClFNO₄, contains two independent molecules. The dihedral angles between the pyridine and benzene rings are 83.3 (2) and 69.7 (1)° in the two molecules. In the crystal structure, intermolecular C—H

N and C—H

F hydrogen bonds link the molecules into chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021319/hk2242sup1.cif Contains datablocks I, ls
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021319/hk2242Isup2.hkl Contains datablock I

CCDC reference: 651408

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.060
wR factor = 0.170
Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond  C1     -   C2     ...       1.22 Ang.
PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.21 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C4      ..       5.12 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT320_ALERT_2_C Check Hybridisation of  C1     in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C18    in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  F2      ..       3.21 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H13 Cl F N O4

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.98
           From the CIF: _reflns_number_total               3550
           Count of symmetry unique reflns         3566
           Completeness (_total/calc)             99.55%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), can be used as an important herbicide (Chen et al., 2005). We herein report its crystal structure.

The asymmetric unit of the title compound, (I), (Fig. 1), contains two independent molecules and the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987).

Rings A (C7—C12), B (N1/C13—C17), C (C24—C29) and D (N2/C30—C34) are, of course, planar and the dihedral angles between them are A/B = 83.3 (2)° and C/D = 69.7 (1)°.

As can be seen from the packing diagram (Fig. 2), the intermolecular C—H···N and C—H···F hydrogen bonds (Table 2) link the molecules into chains, in which they may be effective in the stabilization of the crystal structure. Dipol-dipol and van der Waals interactions are also effective in the molecular packing.

Related literature top

For general background, see: Chen et al. (2005); Allen et al. (1987). For related literature, see: Chen et al. (2005).

Experimental top

The title compound, (I) was prepared by the literature method (Chen et al., 2005). The crystals were obtained by dissolving the title compound (0.5 g) in ethanol (50 ml) and evaporating the solvent slowly at room temperature for about 20 d.

Structure description top

The title compound, (I), can be used as an important herbicide (Chen et al., 2005). We herein report its crystal structure.

The asymmetric unit of the title compound, (I), (Fig. 1), contains two independent molecules and the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987).

Rings A (C7—C12), B (N1/C13—C17), C (C24—C29) and D (N2/C30—C34) are, of course, planar and the dihedral angles between them are A/B = 83.3 (2)° and C/D = 69.7 (1)°.

For general background, see: Chen et al. (2005); Allen et al. (1987). For related literature, see: Chen et al. (2005).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(R)-Prop-2-ynyl 2-(4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy)propanoate top

Crystal data top

C₁₇H₁₃ClFNO₄	F(000) = 1440
M_r = 349.73	D_x = 1.372 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 25 reflections
a = 37.867 (3) Å	θ = 10–13°
b = 8.1682 (11) Å	µ = 0.26 mm⁻¹
c = 10.9666 (14) Å	T = 298 K
β = 93.45 (3)°	Block, colourless
V = 3385.8 (7) Å³	0.40 × 0.30 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2149 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ω/2θ scans	h = −46→46
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.905, T_max = 0.975	l = 0→13
3550 measured reflections	3 standard reflections every 200 reflections
3550 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.08P)² + 2P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3550 reflections	Δρ_max = 0.20 e Å⁻³
433 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 57 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.28 (17)

Crystal data top

C₁₇H₁₃ClFNO₄	V = 3385.8 (7) Å³
M_r = 349.73	Z = 8
Monoclinic, C2	Mo Kα radiation
a = 37.867 (3) Å	µ = 0.26 mm⁻¹
b = 8.1682 (11) Å	T = 298 K
c = 10.9666 (14) Å	0.40 × 0.30 × 0.10 mm
β = 93.45 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2149 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.905, T_max = 0.975	3 standard reflections every 200 reflections
3550 measured reflections	intensity decay: none
3550 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.170	Δρ_max = 0.20 e Å⁻³
S = 1.01	Δρ_min = −0.21 e Å⁻³
3550 reflections	Absolute structure: Flack (1983), with 57 Friedel pairs
433 parameters	Absolute structure parameter: 0.28 (17)
1 restraint

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	0.73191 (7)	0.0546 (6)	0.65536 (19)	0.1523 (13)
F1	0.80852 (10)	0.0049 (9)	0.2946 (4)	0.128 (2)
O1	0.59918 (12)	−0.4128 (5)	−0.1417 (4)	0.0795 (13)
O2	0.58657 (14)	−0.1584 (7)	−0.0911 (5)	0.0910 (14)
O3	0.64375 (11)	−0.0513 (5)	−0.2150 (4)	0.0740 (12)
O4	0.75258 (11)	0.0099 (9)	0.1393 (4)	0.0987 (18)
C1	0.5857 (2)	−0.7883 (10)	−0.0409 (7)	0.094 (2)
H1B	0.5821	−0.8706	0.0196	0.113*
C2	0.57952 (18)	−0.6421 (9)	−0.0437 (6)	0.0756 (18)
C3	0.57404 (18)	−0.4697 (9)	−0.0569 (6)	0.0770 (18)
H3A	0.5780	−0.4152	0.0214	0.092*
H3B	0.5500	−0.4473	−0.0884	0.092*
C4	0.60275 (17)	−0.2506 (8)	−0.1507 (5)	0.0661 (16)
C5	0.62827 (18)	−0.2057 (8)	−0.2441 (5)	0.0696 (16)
H5A	0.6467	−0.2895	−0.2468	0.084*
C6	0.6092 (2)	−0.1865 (11)	−0.3709 (6)	0.097 (2)
H6A	0.6261	−0.1585	−0.4293	0.146*
H6B	0.5918	−0.1013	−0.3683	0.146*
H6C	0.5978	−0.2877	−0.3943	0.146*
C7	0.66962 (16)	−0.0437 (8)	−0.1219 (5)	0.0677 (15)
C8	0.68113 (16)	−0.1778 (9)	−0.0530 (5)	0.0744 (16)
H8A	0.6709	−0.2803	−0.0663	0.089*
C9	0.70829 (17)	−0.1555 (10)	0.0365 (6)	0.0807 (18)
H9A	0.7168	−0.2446	0.0823	0.097*
C10	0.72253 (16)	−0.0047 (10)	0.0578 (6)	0.0750 (17)
C11	0.71068 (18)	0.1297 (10)	−0.0103 (6)	0.0777 (17)
H11A	0.7207	0.2323	0.0035	0.093*
C12	0.68367 (16)	0.1082 (8)	−0.0991 (5)	0.0691 (15)
H12A	0.6749	0.1978	−0.1437	0.083*
C13	0.74679 (18)	0.0236 (10)	0.2593 (6)	0.0795 (17)
C14	0.77636 (18)	0.0194 (11)	0.3391 (7)	0.0830 (19)
C15	0.7726 (2)	0.0291 (14)	0.4631 (7)	0.106 (2)
H15A	0.7922	0.0250	0.5184	0.127*
C16	0.73960 (19)	0.0449 (13)	0.5018 (7)	0.093 (2)
C17	0.7112 (2)	0.0383 (12)	0.4175 (6)	0.098 (2)
H17A	0.6884	0.0398	0.4452	0.118*
N1	0.71505 (14)	0.0298 (10)	0.2976 (5)	0.0896 (17)
Cl2	0.48191 (7)	−0.2837 (4)	0.8097 (3)	0.1412 (11)
F2	0.49168 (14)	0.3296 (7)	0.8523 (4)	0.1204 (17)
O5	0.62661 (11)	0.7285 (6)	0.1873 (4)	0.0733 (11)
O6	0.65936 (12)	0.7104 (6)	0.3643 (4)	0.0802 (12)
O7	0.64525 (11)	0.3785 (6)	0.3673 (4)	0.0737 (12)
O8	0.53381 (13)	0.3496 (6)	0.6671 (4)	0.0879 (14)
C18	0.5838 (2)	1.0156 (11)	0.3580 (7)	0.095 (2)
H18A	0.5783	1.0352	0.4410	0.114*
C19	0.60420 (19)	0.9631 (9)	0.2865 (6)	0.0768 (18)
C20	0.6280 (2)	0.9058 (8)	0.1992 (6)	0.0787 (19)
H20A	0.6519	0.9389	0.2246	0.094*
H20B	0.6219	0.9555	0.1205	0.094*
C21	0.64394 (16)	0.6436 (8)	0.2784 (6)	0.0631 (15)
C22	0.64261 (18)	0.4643 (8)	0.2552 (5)	0.0684 (16)
H22A	0.6204	0.4360	0.2098	0.082*
C23	0.6734 (2)	0.4140 (10)	0.1834 (6)	0.098 (2)
H23A	0.6723	0.4709	0.1066	0.147*
H23B	0.6724	0.2981	0.1690	0.147*
H23C	0.6951	0.4409	0.2287	0.147*
C24	0.61667 (15)	0.3803 (8)	0.4379 (5)	0.0608 (13)
C25	0.62184 (17)	0.3046 (8)	0.5506 (5)	0.0695 (15)
H25A	0.6439	0.2621	0.5750	0.083*
C26	0.59456 (18)	0.2923 (9)	0.6255 (6)	0.0727 (16)
H26A	0.5981	0.2424	0.7015	0.087*
C27	0.55670 (16)	0.4337 (8)	0.4797 (6)	0.0700 (15)
H27A	0.5348	0.4789	0.4568	0.084*
C28	0.58474 (17)	0.4471 (8)	0.4028 (6)	0.0727 (16)
H28A	0.5816	0.5012	0.3283	0.087*
C29	0.56190 (17)	0.3531 (8)	0.5894 (5)	0.0714 (16)
C30	0.52142 (16)	0.2002 (9)	0.6994 (6)	0.0710 (15)
C31	0.49999 (18)	0.1923 (10)	0.7938 (7)	0.0802 (18)
C32	0.48724 (19)	0.0456 (12)	0.8321 (6)	0.091 (2)
H32A	0.4730	0.0389	0.8980	0.109*
C33	0.49657 (19)	−0.0919 (10)	0.7685 (8)	0.089 (2)
C34	0.5168 (2)	−0.0765 (10)	0.6734 (8)	0.089 (2)
H34A	0.5223	−0.1701	0.6301	0.107*
N2	0.52953 (15)	0.0690 (8)	0.6374 (5)	0.0831 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.146 (2)	0.243 (4)	0.0682 (11)	−0.002 (3)	0.0094 (12)	−0.027 (2)
F1	0.067 (2)	0.213 (6)	0.103 (3)	−0.017 (3)	−0.007 (2)	0.012 (4)
O1	0.107 (3)	0.055 (3)	0.077 (3)	−0.008 (2)	0.019 (2)	−0.008 (2)
O2	0.103 (4)	0.082 (3)	0.090 (3)	0.005 (3)	0.016 (3)	−0.004 (3)
O3	0.088 (3)	0.068 (3)	0.065 (2)	−0.008 (2)	−0.007 (2)	0.004 (2)
O4	0.064 (2)	0.163 (5)	0.068 (3)	−0.023 (3)	0.005 (2)	0.000 (3)
C1	0.114 (6)	0.082 (6)	0.085 (5)	−0.007 (5)	0.000 (4)	0.017 (4)
C2	0.084 (4)	0.085 (5)	0.058 (4)	0.001 (4)	0.001 (3)	0.005 (3)
C3	0.087 (4)	0.069 (4)	0.076 (4)	−0.008 (4)	0.017 (3)	−0.003 (4)
C4	0.079 (4)	0.062 (4)	0.057 (3)	0.008 (3)	0.000 (3)	−0.014 (3)
C5	0.091 (4)	0.061 (4)	0.056 (3)	−0.002 (3)	−0.002 (3)	−0.008 (3)
C6	0.126 (6)	0.109 (6)	0.056 (4)	−0.019 (5)	−0.002 (4)	−0.011 (4)
C7	0.069 (3)	0.075 (4)	0.059 (3)	−0.006 (3)	0.001 (3)	−0.001 (3)
C8	0.073 (4)	0.080 (4)	0.069 (3)	−0.008 (3)	0.000 (3)	0.006 (3)
C9	0.071 (4)	0.101 (4)	0.070 (4)	−0.004 (4)	0.002 (3)	0.018 (4)
C10	0.062 (3)	0.106 (5)	0.058 (3)	0.000 (3)	0.007 (3)	−0.008 (3)
C11	0.081 (4)	0.085 (4)	0.068 (4)	−0.014 (3)	0.013 (3)	−0.013 (3)
C12	0.080 (4)	0.074 (4)	0.055 (3)	0.002 (3)	0.013 (3)	−0.004 (3)
C13	0.078 (4)	0.096 (5)	0.065 (3)	−0.015 (4)	0.003 (3)	−0.010 (4)
C14	0.068 (3)	0.097 (5)	0.085 (4)	−0.014 (4)	0.007 (3)	0.002 (4)
C15	0.104 (4)	0.135 (6)	0.077 (4)	−0.001 (5)	−0.005 (4)	−0.002 (5)
C16	0.092 (4)	0.112 (5)	0.077 (4)	−0.007 (4)	0.010 (3)	−0.011 (4)
C17	0.090 (4)	0.128 (6)	0.077 (4)	0.001 (5)	0.010 (3)	−0.015 (5)
N1	0.075 (3)	0.121 (5)	0.073 (3)	0.007 (3)	0.007 (3)	−0.014 (4)
Cl2	0.1080 (16)	0.125 (2)	0.187 (3)	−0.0316 (16)	−0.0179 (16)	0.059 (2)
F2	0.127 (4)	0.129 (4)	0.111 (3)	−0.026 (3)	0.051 (3)	−0.030 (3)
O5	0.087 (3)	0.077 (3)	0.054 (2)	0.009 (2)	−0.008 (2)	−0.003 (2)
O6	0.093 (3)	0.072 (3)	0.072 (3)	0.001 (3)	−0.020 (2)	0.000 (2)
O7	0.085 (3)	0.077 (3)	0.060 (2)	0.016 (2)	0.015 (2)	0.014 (2)
O8	0.089 (3)	0.091 (4)	0.086 (3)	−0.005 (3)	0.026 (2)	−0.002 (3)
C18	0.106 (6)	0.092 (6)	0.084 (5)	0.010 (5)	−0.026 (4)	−0.016 (4)
C19	0.098 (5)	0.063 (4)	0.066 (4)	0.000 (4)	−0.026 (4)	−0.008 (3)
C20	0.118 (5)	0.063 (4)	0.054 (4)	0.004 (4)	−0.003 (4)	0.007 (3)
C21	0.068 (4)	0.068 (4)	0.054 (3)	0.010 (3)	0.008 (3)	0.010 (3)
C22	0.087 (4)	0.069 (4)	0.049 (3)	0.006 (3)	0.006 (3)	0.002 (3)
C23	0.132 (6)	0.095 (6)	0.070 (4)	0.031 (5)	0.042 (4)	0.013 (4)
C24	0.068 (3)	0.062 (3)	0.053 (3)	−0.003 (3)	0.003 (2)	0.001 (3)
C25	0.082 (4)	0.070 (4)	0.056 (3)	0.000 (3)	0.001 (3)	0.003 (3)
C26	0.089 (4)	0.080 (4)	0.050 (3)	−0.007 (3)	0.006 (3)	0.001 (3)
C27	0.066 (3)	0.068 (4)	0.075 (3)	−0.001 (3)	0.001 (3)	0.000 (3)
C28	0.081 (4)	0.070 (4)	0.066 (3)	−0.002 (3)	−0.001 (3)	0.007 (3)
C29	0.084 (4)	0.070 (4)	0.061 (3)	−0.005 (3)	0.013 (3)	−0.004 (3)
C30	0.070 (3)	0.078 (4)	0.065 (3)	−0.003 (3)	0.007 (3)	0.001 (3)
C31	0.074 (4)	0.095 (4)	0.072 (4)	−0.003 (4)	0.009 (3)	−0.009 (4)
C32	0.077 (4)	0.120 (5)	0.075 (4)	−0.018 (4)	0.005 (3)	0.011 (4)
C33	0.068 (4)	0.093 (4)	0.105 (5)	−0.017 (4)	−0.009 (3)	0.019 (4)
C34	0.085 (4)	0.073 (4)	0.110 (5)	−0.008 (4)	0.000 (4)	0.000 (4)
N2	0.085 (3)	0.083 (4)	0.083 (3)	−0.010 (3)	0.011 (3)	−0.002 (3)

Geometric parameters (Å, º) top

Cl1—C16	1.728 (7)	Cl2—C33	1.731 (8)
F1—C14	1.344 (7)	F2—C31	1.339 (9)
O1—C4	1.337 (8)	O5—C21	1.353 (7)
O1—C3	1.447 (7)	O5—C20	1.455 (8)
O2—C4	1.191 (7)	O6—C21	1.208 (7)
O3—C7	1.373 (7)	O7—C24	1.368 (7)
O3—C5	1.419 (8)	O7—C22	1.414 (7)
O4—C13	1.352 (7)	O8—C30	1.362 (8)
O4—C10	1.409 (7)	O8—C29	1.402 (7)
C1—C2	1.216 (8)	C18—C19	1.211 (7)
C1—H1B	0.9600	C18—H18A	0.9599
C2—C3	1.430 (11)	C19—C20	1.432 (10)
C3—H3A	0.9700	C20—H20A	0.9700
C3—H3B	0.9700	C20—H20B	0.9700
C4—C5	1.496 (9)	C21—C22	1.487 (9)
C5—C6	1.535 (9)	C22—C23	1.502 (9)
C5—H5A	0.9800	C22—H22A	0.9800
C6—H6A	0.9600	C23—H23A	0.9600
C6—H6B	0.9600	C23—H23B	0.9600
C6—H6C	0.9600	C23—H23C	0.9600
C7—C12	1.367 (9)	C24—C28	1.361 (8)
C7—C8	1.386 (9)	C24—C25	1.385 (8)
C8—C9	1.390 (9)	C25—C26	1.362 (8)
C8—H8A	0.9300	C25—H25A	0.9300
C9—C10	1.359 (10)	C26—C29	1.369 (9)
C9—H9A	0.9300	C26—H26A	0.9300
C10—C11	1.387 (10)	C27—C29	1.376 (9)
C11—C12	1.380 (9)	C27—C28	1.399 (9)
C11—H11A	0.9300	C27—H27A	0.9300
C12—H12A	0.9300	C28—H28A	0.9300
C13—N1	1.298 (8)	C30—N2	1.315 (9)
C13—C14	1.379 (9)	C30—C31	1.354 (9)
C14—C15	1.378 (10)	C31—C32	1.368 (11)
C15—C16	1.352 (10)	C32—C33	1.380 (12)
C15—H15A	0.9300	C32—H32A	0.9300
C16—C17	1.377 (10)	C33—C34	1.335 (11)
C17—N1	1.334 (8)	C34—N2	1.351 (10)
C17—H17A	0.9300	C34—H34A	0.9300

C4—O1—C3	116.0 (5)	C21—O5—C20	115.5 (5)
C7—O3—C5	118.3 (5)	C24—O7—C22	118.0 (5)
C13—O4—C10	116.9 (5)	C30—O8—C29	117.5 (5)
C2—C1—H1B	132.1	C19—C18—H18A	149.0
C1—C2—C3	174.8 (8)	C18—C19—C20	178.0 (8)
C2—C3—O1	106.5 (6)	C19—C20—O5	111.4 (6)
C2—C3—H3A	110.4	C19—C20—H20A	109.3
O1—C3—H3A	110.4	O5—C20—H20A	109.3
C2—C3—H3B	110.4	C19—C20—H20B	109.3
O1—C3—H3B	110.4	O5—C20—H20B	109.3
H3A—C3—H3B	108.6	H20A—C20—H20B	108.0
O2—C4—O1	122.0 (6)	O6—C21—O5	122.3 (6)
O2—C4—C5	126.6 (6)	O6—C21—C22	126.0 (6)
O1—C4—C5	111.4 (5)	O5—C21—C22	111.6 (6)
O3—C5—C4	109.8 (5)	O7—C22—C21	109.8 (5)
O3—C5—C6	106.1 (5)	O7—C22—C23	107.7 (5)
C4—C5—C6	111.0 (5)	C21—C22—C23	109.9 (6)
O3—C5—H5A	110.0	O7—C22—H22A	109.8
C4—C5—H5A	110.0	C21—C22—H22A	109.8
C6—C5—H5A	110.0	C23—C22—H22A	109.8
C5—C6—H6A	109.5	C22—C23—H23A	109.5
C5—C6—H6B	109.5	C22—C23—H23B	109.5
H6A—C6—H6B	109.5	H23A—C23—H23B	109.5
C5—C6—H6C	109.5	C22—C23—H23C	109.5
H6A—C6—H6C	109.5	H23A—C23—H23C	109.5
H6B—C6—H6C	109.5	H23B—C23—H23C	109.5
C12—C7—O3	115.4 (6)	C28—C24—O7	124.3 (5)
C12—C7—C8	120.7 (6)	C28—C24—C25	120.5 (5)
O3—C7—C8	123.9 (6)	O7—C24—C25	115.2 (5)
C7—C8—C9	118.5 (7)	C26—C25—C24	120.0 (6)
C7—C8—H8A	120.8	C26—C25—H25A	120.0
C9—C8—H8A	120.8	C24—C25—H25A	120.0
C10—C9—C8	120.6 (7)	C25—C26—C29	120.2 (6)
C10—C9—H9A	119.7	C25—C26—H26A	119.9
C8—C9—H9A	119.7	C29—C26—H26A	119.9
C9—C10—C11	120.8 (6)	C29—C27—C28	119.4 (6)
C9—C10—O4	118.9 (7)	C29—C27—H27A	120.3
C11—C10—O4	119.8 (7)	C28—C27—H27A	120.3
C12—C11—C10	118.8 (7)	C24—C28—C27	119.5 (6)
C12—C11—H11A	120.6	C24—C28—H28A	120.3
C10—C11—H11A	120.6	C27—C28—H28A	120.3
C7—C12—C11	120.5 (7)	C26—C29—C27	120.4 (6)
C7—C12—H12A	119.7	C26—C29—O8	121.5 (6)
C11—C12—H12A	119.7	C27—C29—O8	117.8 (6)
N1—C13—O4	121.8 (6)	N2—C30—C31	121.7 (7)
N1—C13—C14	121.8 (6)	N2—C30—O8	120.0 (5)
O4—C13—C14	116.3 (6)	C31—C30—O8	118.2 (7)
F1—C14—C15	120.8 (7)	F2—C31—C30	119.7 (7)
F1—C14—C13	119.3 (6)	F2—C31—C32	119.3 (6)
C15—C14—C13	119.8 (7)	C30—C31—C32	121.0 (8)
C16—C15—C14	117.8 (7)	C31—C32—C33	116.9 (6)
C16—C15—H15A	121.1	C31—C32—H32A	121.6
C14—C15—H15A	121.1	C33—C32—H32A	121.6
C15—C16—C17	119.1 (7)	C34—C33—C32	119.6 (7)
C15—C16—Cl1	121.6 (6)	C34—C33—Cl2	119.8 (7)
C17—C16—Cl1	119.0 (6)	C32—C33—Cl2	120.6 (6)
N1—C17—C16	122.4 (7)	C33—C34—N2	122.9 (8)
N1—C17—H17A	118.8	C33—C34—H34A	118.6
C16—C17—H17A	118.8	N2—C34—H34A	118.6
C13—N1—C17	118.7 (6)	C30—N2—C34	117.8 (6)

C4—O1—C3—C2	−168.8 (6)	C21—O5—C20—C19	−77.2 (7)
C3—O1—C4—O2	1.1 (9)	C20—O5—C21—O6	0.4 (9)
C3—O1—C4—C5	−177.8 (5)	C20—O5—C21—C22	−177.1 (6)
C7—O3—C5—C4	76.3 (7)	C24—O7—C22—C21	72.7 (7)
C7—O3—C5—C6	−163.7 (5)	C24—O7—C22—C23	−167.7 (6)
O2—C4—C5—O3	27.8 (9)	O6—C21—C22—O7	29.9 (10)
O1—C4—C5—O3	−153.4 (5)	O5—C21—C22—O7	−152.7 (5)
O2—C4—C5—C6	−89.2 (8)	O6—C21—C22—C23	−88.4 (8)
O1—C4—C5—C6	89.6 (7)	O5—C21—C22—C23	89.0 (7)
C5—O3—C7—C12	179.5 (6)	C22—O7—C24—C28	6.0 (9)
C5—O3—C7—C8	−1.3 (9)	C22—O7—C24—C25	−175.4 (6)
C12—C7—C8—C9	−2.6 (10)	C28—C24—C25—C26	1.9 (10)
O3—C7—C8—C9	178.1 (6)	O7—C24—C25—C26	−176.7 (6)
C7—C8—C9—C10	1.7 (10)	C24—C25—C26—C29	0.7 (10)
C8—C9—C10—C11	−1.0 (10)	O7—C24—C28—C27	176.3 (6)
C8—C9—C10—O4	−172.9 (5)	C25—C24—C28—C27	−2.2 (10)
C13—O4—C10—C9	−85.5 (9)	C29—C27—C28—C24	−0.1 (10)
C13—O4—C10—C11	102.5 (8)	C25—C26—C29—C27	−3.0 (10)
C9—C10—C11—C12	1.1 (9)	C25—C26—C29—O8	−176.7 (6)
O4—C10—C11—C12	172.9 (5)	C28—C27—C29—C26	2.7 (10)
O3—C7—C12—C11	−177.9 (5)	C28—C27—C29—O8	176.6 (6)
C8—C7—C12—C11	2.8 (10)	C30—O8—C29—C26	−64.8 (8)
C10—C11—C12—C7	−2.0 (9)	C30—O8—C29—C27	121.3 (7)
C10—O4—C13—N1	−2.7 (12)	C29—O8—C30—N2	−16.0 (9)
C10—O4—C13—C14	173.0 (7)	C29—O8—C30—C31	165.8 (6)
N1—C13—C14—F1	176.7 (8)	N2—C30—C31—F2	−178.3 (6)
O4—C13—C14—F1	1.0 (12)	O8—C30—C31—F2	−0.1 (10)
N1—C13—C14—C15	−2.9 (14)	N2—C30—C31—C32	3.1 (11)
O4—C13—C14—C15	−178.6 (8)	O8—C30—C31—C32	−178.7 (6)
F1—C14—C15—C16	179.5 (9)	F2—C31—C32—C33	179.9 (7)
C13—C14—C15—C16	−0.9 (15)	C30—C31—C32—C33	−1.5 (10)
C14—C15—C16—C17	4.8 (16)	C31—C32—C33—C34	−0.9 (11)
C14—C15—C16—Cl1	178.8 (8)	C31—C32—C33—Cl2	179.9 (6)
C15—C16—C17—N1	−5.4 (16)	C32—C33—C34—N2	1.8 (12)
Cl1—C16—C17—N1	−179.6 (8)	Cl2—C33—C34—N2	−179.0 (6)
O4—C13—N1—C17	178.0 (8)	C31—C30—N2—C34	−2.2 (10)
C14—C13—N1—C17	2.5 (13)	O8—C30—N2—C34	179.7 (7)
C16—C17—N1—C13	1.7 (15)	C33—C34—N2—C30	−0.2 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···F1ⁱ	0.98	2.47	3.433 (9)	169
C20—H20A···N1ⁱⁱ	0.97	2.58	3.554 (9)	179

Symmetry codes: (i) −x+3/2, y−1/2, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃ClFNO₄
M_r	349.73
Crystal system, space group	Monoclinic, C2
Temperature (K)	298
a, b, c (Å)	37.867 (3), 8.1682 (11), 10.9666 (14)
β (°)	93.45 (3)
V (Å³)	3385.8 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.905, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	3550, 3550, 2149
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.170, 1.01
No. of reflections	3550
No. of parameters	433
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21
Absolute structure	Flack (1983), with 57 Friedel pairs
Absolute structure parameter	0.28 (17)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C4	1.337 (8)	O5—C21	1.353 (7)
O1—C3	1.447 (7)	O5—C20	1.455 (8)
O2—C4	1.191 (7)	O6—C21	1.208 (7)
O3—C7	1.373 (7)	O7—C24	1.368 (7)
O3—C5	1.419 (8)	O7—C22	1.414 (7)
O4—C13	1.352 (7)	O8—C30	1.362 (8)
O4—C10	1.409 (7)	O8—C29	1.402 (7)
C13—N1	1.298 (8)	C30—N2	1.315 (9)
C17—N1	1.334 (8)	C34—N2	1.351 (10)

O2—C4—O1	122.0 (6)	N1—C13—C14	121.8 (6)
O2—C4—C5	126.6 (6)	O4—C13—C14	116.3 (6)
O1—C4—C5	111.4 (5)	F1—C14—C15	120.8 (7)
O3—C5—C4	109.8 (5)	F1—C14—C13	119.3 (6)
O3—C5—C6	106.1 (5)	C28—C24—O7	124.3 (5)
N1—C13—O4	121.8 (6)	C26—C29—O8	121.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···F1ⁱ	0.98	2.47	3.433 (9)	169
C20—H20A···N1ⁱⁱ	0.97	2.58	3.554 (9)	179

Symmetry codes: (i) −x+3/2, y−1/2, −z; (ii) x, y+1, z.

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