Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021319/hk2242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021319/hk2242Isup2.hkl |
CCDC reference: 651408
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
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.
H atoms were positioned geometrically, with C—H = 0.93 (for aromatic H), 0.96 and 0.98 (for methine H), 0.97 (for methylene H) and 0.96 Å (for methyl H), and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
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.
For general background, see: Chen et al. (2005); Allen et al. (1987). For related literature, see: Chen et al. (2005).
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.
C17H13ClFNO4 | F(000) = 1440 |
Mr = 349.73 | Dx = 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 |
Enraf–Nonius CAD-4 diffractometer | 2149 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ω/2θ scans | h = −46→46 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.905, Tmax = 0.975 | l = 0→13 |
3550 measured reflections | 3 standard reflections every 200 reflections |
3550 independent reflections | intensity decay: none |
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(Fo2) + (0.08P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3550 reflections | Δρmax = 0.20 e Å−3 |
433 parameters | Δρmin = −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) |
C17H13ClFNO4 | V = 3385.8 (7) Å3 |
Mr = 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)° |
Enraf–Nonius CAD-4 diffractometer | 2149 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.905, Tmax = 0.975 | 3 standard reflections every 200 reflections |
3550 measured reflections | intensity decay: none |
3550 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.170 | Δρmax = 0.20 e Å−3 |
S = 1.01 | Δρmin = −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 |
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 | 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) |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.905, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3550, 3550, 2149 |
Rint | 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 |
Δρmax, Δρmin (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.
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) |
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. |
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.