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In the title compound, C16H11ClO6, the dihedral angle between the two benzene rings is 86.9 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605197X/hb2227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605197X/hb2227Isup2.hkl
Contains datablock I

CCDC reference: 633868

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.119
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Methyl 7-(4-chlorobenzoyloxy)-1,3-benzodioxole-5-carboxylate top
Crystal data top
C16H11ClO6F(000) = 688
Mr = 334.70Dx = 1.494 Mg m3
Monoclinic, P21/nMelting point = 387–388 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.240 (5) ÅCell parameters from 1349 reflections
b = 6.618 (3) Åθ = 3.3–23.6°
c = 18.471 (8) ŵ = 0.29 mm1
β = 95.879 (7)°T = 294 K
V = 1488.3 (11) Å3Block, colourless
Z = 40.24 × 0.20 × 0.14 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2625 independent reflections
Radiation source: fine-focus sealed tube1494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1014
Tmin = 0.935, Tmax = 0.961k = 73
5956 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.1924P]
where P = (Fo2 + 2Fc2)/3
2625 reflections(Δ/σ)max = 0.003
209 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
Cl10.38584 (8)1.06935 (14)1.12418 (5)0.0853 (4)
O10.08106 (16)0.2577 (3)0.91705 (11)0.0616 (6)
O20.11543 (17)0.3449 (3)0.80019 (10)0.0654 (6)
O30.11086 (17)0.1418 (3)0.66590 (10)0.0608 (6)
O40.17457 (16)0.3920 (3)0.74724 (11)0.0627 (6)
O50.13236 (15)0.3991 (3)0.90012 (10)0.0523 (5)
O60.29061 (16)0.2322 (3)0.92636 (12)0.0676 (6)
C10.1828 (3)0.5103 (5)0.82046 (18)0.0784 (11)
H1A0.13910.60060.85210.118*
H1B0.21200.58170.77750.118*
H1C0.24210.45850.84520.118*
C20.0690 (2)0.2298 (4)0.85420 (16)0.0488 (7)
C30.0034 (2)0.0646 (4)0.82650 (14)0.0437 (7)
C40.0181 (2)0.0575 (4)0.75377 (14)0.0477 (7)
H40.00830.15640.72070.057*
C50.0793 (2)0.1004 (4)0.73341 (14)0.0456 (7)
C60.1808 (3)0.3136 (5)0.67526 (16)0.0673 (9)
H6A0.15750.41570.63930.081*
H6B0.25580.27550.66910.081*
C70.1176 (2)0.2494 (4)0.78097 (14)0.0448 (7)
C80.0969 (2)0.2431 (4)0.85271 (15)0.0458 (7)
C90.0362 (2)0.0837 (4)0.87499 (14)0.0459 (7)
H90.02170.07570.92330.055*
C100.2346 (2)0.3763 (4)0.93570 (14)0.0445 (7)
C110.2660 (2)0.5473 (4)0.98403 (13)0.0400 (6)
C120.3705 (2)0.5448 (4)1.02112 (14)0.0493 (7)
H120.41570.43331.01700.059*
C130.4077 (2)0.7050 (5)1.06382 (15)0.0548 (8)
H130.47820.70401.08800.066*
C140.3395 (3)0.8666 (4)1.07026 (14)0.0510 (8)
C150.2345 (2)0.8708 (4)1.03524 (15)0.0520 (8)
H150.18890.98111.04060.062*
C160.1980 (2)0.7096 (4)0.99215 (14)0.0470 (7)
H160.12710.71050.96850.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1036 (7)0.0689 (6)0.0792 (6)0.0138 (5)0.0104 (5)0.0264 (5)
O10.0680 (14)0.0677 (15)0.0511 (12)0.0057 (11)0.0161 (11)0.0040 (11)
O20.0771 (15)0.0627 (14)0.0571 (12)0.0302 (12)0.0105 (11)0.0039 (11)
O30.0776 (15)0.0624 (14)0.0444 (11)0.0170 (12)0.0161 (10)0.0022 (10)
O40.0727 (14)0.0534 (14)0.0648 (13)0.0178 (11)0.0206 (11)0.0056 (11)
O50.0465 (12)0.0522 (13)0.0572 (12)0.0022 (9)0.0004 (10)0.0195 (10)
O60.0619 (14)0.0560 (14)0.0826 (15)0.0122 (12)0.0043 (12)0.0222 (12)
C10.086 (2)0.067 (2)0.086 (2)0.030 (2)0.023 (2)0.0018 (19)
C20.0445 (17)0.0520 (19)0.0506 (18)0.0010 (14)0.0082 (15)0.0020 (16)
C30.0435 (16)0.0443 (17)0.0435 (16)0.0018 (13)0.0063 (13)0.0006 (14)
C40.0513 (17)0.0459 (18)0.0453 (16)0.0051 (14)0.0027 (14)0.0070 (14)
C50.0487 (17)0.0497 (19)0.0389 (15)0.0016 (15)0.0067 (13)0.0007 (14)
C60.080 (2)0.065 (2)0.060 (2)0.0194 (19)0.0195 (18)0.0004 (17)
C70.0437 (16)0.0417 (18)0.0495 (17)0.0027 (14)0.0081 (14)0.0019 (14)
C80.0421 (16)0.0461 (18)0.0488 (17)0.0014 (14)0.0031 (14)0.0136 (15)
C90.0423 (16)0.0544 (19)0.0416 (15)0.0003 (14)0.0068 (13)0.0054 (15)
C100.0451 (18)0.0467 (19)0.0429 (16)0.0024 (15)0.0104 (14)0.0009 (14)
C110.0426 (16)0.0420 (17)0.0368 (14)0.0027 (13)0.0106 (13)0.0039 (13)
C120.0454 (17)0.0544 (19)0.0487 (16)0.0034 (14)0.0082 (14)0.0050 (15)
C130.0489 (18)0.065 (2)0.0489 (17)0.0062 (17)0.0008 (15)0.0059 (16)
C140.064 (2)0.049 (2)0.0402 (15)0.0088 (16)0.0063 (15)0.0054 (14)
C150.061 (2)0.0418 (18)0.0528 (17)0.0057 (15)0.0053 (16)0.0055 (15)
C160.0488 (17)0.0480 (19)0.0437 (15)0.0008 (15)0.0025 (14)0.0019 (14)
Geometric parameters (Å, º) top
Cl1—C141.732 (3)C4—H40.9300
O1—C21.199 (3)C5—C71.371 (4)
O2—C21.335 (3)C6—H6A0.9700
O2—C11.442 (3)C6—H6B0.9700
O3—C51.370 (3)C7—C81.375 (4)
O3—C61.422 (3)C8—C91.377 (4)
O4—C71.362 (3)C9—H90.9300
O4—C61.436 (3)C10—C111.468 (4)
O5—C101.361 (3)C11—C161.377 (4)
O5—C81.394 (3)C11—C121.387 (4)
O6—C101.198 (3)C12—C131.371 (4)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—C141.369 (4)
C1—H1C0.9600C13—H130.9300
C2—C31.479 (4)C14—C151.378 (4)
C3—C91.383 (4)C15—C161.378 (4)
C3—C41.396 (4)C15—H150.9300
C4—C51.362 (4)C16—H160.9300
C2—O2—C1116.7 (2)O4—C7—C8128.0 (2)
C5—O3—C6105.7 (2)C5—C7—C8120.8 (3)
C7—O4—C6104.6 (2)C7—C8—C9118.0 (2)
C10—O5—C8115.7 (2)C7—C8—O5120.5 (3)
O2—C1—H1A109.5C9—C8—O5121.5 (2)
O2—C1—H1B109.5C8—C9—C3120.9 (2)
H1A—C1—H1B109.5C8—C9—H9119.5
O2—C1—H1C109.5C3—C9—H9119.5
H1A—C1—H1C109.5O6—C10—O5122.0 (2)
H1B—C1—H1C109.5O6—C10—C11125.7 (3)
O1—C2—O2123.4 (3)O5—C10—C11112.3 (2)
O1—C2—C3125.0 (3)C16—C11—C12119.5 (2)
O2—C2—C3111.6 (2)C16—C11—C10122.9 (2)
C9—C3—C4120.8 (3)C12—C11—C10117.5 (2)
C9—C3—C2117.9 (2)C13—C12—C11120.7 (3)
C4—C3—C2121.4 (2)C13—C12—H12119.7
C5—C4—C3117.1 (2)C11—C12—H12119.7
C5—C4—H4121.5C14—C13—C12118.9 (3)
C3—C4—H4121.5C14—C13—H13120.5
C4—C5—O3128.3 (2)C12—C13—H13120.5
C4—C5—C7122.5 (3)C13—C14—C15121.5 (3)
O3—C5—C7109.3 (2)C13—C14—Cl1119.2 (2)
O3—C6—O4108.2 (2)C15—C14—Cl1119.3 (2)
O3—C6—H6A110.1C16—C15—C14119.2 (3)
O4—C6—H6A110.1C16—C15—H15120.4
O3—C6—H6B110.1C14—C15—H15120.4
O4—C6—H6B110.1C11—C16—C15120.2 (3)
H6A—C6—H6B108.4C11—C16—H16119.9
O4—C7—C5111.2 (2)C15—C16—H16119.9
C1—O2—C2—O10.2 (4)C5—C7—C8—O5177.5 (2)
C1—O2—C2—C3179.3 (2)C10—O5—C8—C789.9 (3)
O1—C2—C3—C98.4 (4)C10—O5—C8—C993.2 (3)
O2—C2—C3—C9170.8 (2)C7—C8—C9—C30.4 (4)
O1—C2—C3—C4171.7 (3)O5—C8—C9—C3176.5 (2)
O2—C2—C3—C49.2 (4)C4—C3—C9—C80.6 (4)
C9—C3—C4—C50.1 (4)C2—C3—C9—C8179.3 (2)
C2—C3—C4—C5180.0 (2)C8—O5—C10—O60.5 (4)
C3—C4—C5—O3179.6 (2)C8—O5—C10—C11179.6 (2)
C3—C4—C5—C71.0 (4)O6—C10—C11—C16179.6 (3)
C6—O3—C5—C4175.3 (3)O5—C10—C11—C160.6 (3)
C6—O3—C5—C75.9 (3)O6—C10—C11—C121.5 (4)
C5—O3—C6—O49.6 (3)O5—C10—C11—C12177.5 (2)
C7—O4—C6—O39.5 (3)C16—C11—C12—C132.1 (4)
C6—O4—C7—C55.9 (3)C10—C11—C12—C13176.1 (3)
C6—O4—C7—C8174.1 (3)C11—C12—C13—C141.0 (4)
C4—C5—C7—O4178.8 (2)C12—C13—C14—C150.4 (4)
O3—C5—C7—O40.0 (3)C12—C13—C14—Cl1179.9 (2)
C4—C5—C7—C81.3 (4)C13—C14—C15—C160.7 (4)
O3—C5—C7—C8179.9 (2)Cl1—C14—C15—C16179.8 (2)
O4—C7—C8—C9179.5 (2)C12—C11—C16—C151.8 (4)
C5—C7—C8—C90.5 (4)C10—C11—C16—C15176.4 (2)
O4—C7—C8—O52.6 (4)C14—C15—C16—C110.4 (4)
 

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