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The reaction of 5-chloro-2-hydroxy­benzo­phenone with phospho­rus pentachloride yielded the title compound, C13H8Cl5O2P. This compound can then be decomposed into a 2,5-di­chloro­benzo­phenone by heating. There are two mol­ecules of the title compound in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018719/wk6025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018719/wk6025Isup2.hkl
Contains datablock I

CCDC reference: 251642

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.071
  • Data-to-parameter ratio = 25.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C4 .. 3.01 Ang.
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker,2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C13H8Cl5O2PZ = 4
Mr = 404.41F(000) = 808
Triclinic, P1Dx = 1.698 Mg m3
a = 9.5227 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2195 (7) ÅCell parameters from 7462 reflections
c = 17.5587 (12) Åθ = 2.3–30.4°
α = 73.238 (4)°µ = 1.02 mm1
β = 75.348 (4)°T = 273 K
γ = 87.593 (4)°Block, colorless
V = 1582.07 (19) Å30.21 × 0.17 × 0.13 mm
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
9669 independent reflections
Radiation source: fine-focus sealed tube8283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.817, Tmax = 0.879k = 1414
61218 measured reflectionsl = 2525
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0369P)2 + 0.3855P]
where P = (Fo2 + 2Fc2)/3
9669 reflections(Δ/σ)max = 0.002
379 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.39 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
P10.13974 (3)0.76283 (3)0.699523 (18)0.01543 (6)
P20.52687 (3)0.27191 (3)0.78272 (2)0.01898 (7)
Cl10.45493 (3)0.69691 (3)0.50420 (2)0.02724 (7)
Cl20.22158 (4)0.87340 (3)0.468955 (18)0.02478 (7)
Cl30.16681 (3)0.23039 (3)0.55572 (2)0.02343 (7)
Cl40.07830 (4)0.94175 (3)0.70573 (2)0.02575 (7)
Cl50.32895 (3)0.79918 (3)0.66931 (2)0.02687 (7)
Cl60.03597 (3)0.28948 (3)1.071648 (17)0.01839 (6)
Cl70.28474 (3)0.12613 (3)1.039248 (18)0.01940 (6)
Cl80.32268 (3)0.76368 (3)0.99378 (2)0.02212 (6)
Cl90.54032 (4)0.07053 (3)0.80646 (2)0.03011 (8)
Cl100.37796 (4)0.31984 (4)0.71823 (2)0.03195 (8)
O10.02723 (9)0.75330 (8)0.61792 (5)0.01622 (16)
O20.15010 (10)0.64852 (9)0.77330 (5)0.02134 (18)
O30.44815 (9)0.28127 (8)0.87097 (5)0.01741 (16)
O40.66453 (11)0.34640 (12)0.74122 (7)0.0378 (3)
C10.27050 (12)0.73667 (12)0.54840 (7)0.0159 (2)
C20.16518 (12)0.61616 (11)0.56818 (7)0.0142 (2)
C30.01698 (12)0.62775 (11)0.60313 (7)0.0145 (2)
C40.08346 (12)0.52235 (12)0.62118 (7)0.0160 (2)
H40.18120.53430.64290.019*
C50.03828 (13)0.39850 (12)0.60686 (7)0.0162 (2)
H50.10460.32650.61940.019*
C60.10834 (13)0.38494 (12)0.57338 (7)0.0162 (2)
C70.20937 (12)0.49165 (12)0.55359 (7)0.0161 (2)
H70.30670.48000.53060.019*
C80.27608 (12)0.78307 (11)0.62247 (7)0.0147 (2)
C90.24355 (12)0.68792 (12)0.70028 (7)0.0170 (2)
H90.21400.59900.70650.020*
C100.25530 (13)0.72601 (13)0.76821 (8)0.0198 (2)
H100.23430.66220.81980.024*
C110.29820 (14)0.85889 (14)0.75966 (8)0.0226 (2)
H110.30410.88450.80550.027*
C120.33218 (14)0.95336 (13)0.68218 (9)0.0242 (3)
H120.36191.04210.67620.029*
C130.32203 (13)0.91584 (12)0.61355 (8)0.0196 (2)
H130.34580.97920.56180.024*
C140.18971 (12)0.26992 (11)0.99076 (7)0.0142 (2)
C150.29254 (12)0.39614 (11)0.95896 (7)0.0143 (2)
C160.42031 (12)0.39987 (11)0.89709 (7)0.0152 (2)
C170.51970 (13)0.50929 (12)0.86723 (7)0.0174 (2)
H170.60500.50720.82770.021*
C180.49027 (13)0.62247 (12)0.89719 (7)0.0177 (2)
H180.55510.69730.87740.021*
C190.36323 (13)0.62196 (12)0.95676 (7)0.0165 (2)
C200.26536 (12)0.50973 (12)0.98883 (7)0.0160 (2)
H200.18220.51071.03000.019*
C210.12703 (11)0.24326 (11)0.92468 (7)0.0136 (2)
C220.06552 (12)0.35417 (11)0.87725 (7)0.0157 (2)
H220.07160.44060.88400.019*
C230.00433 (13)0.33606 (12)0.82034 (8)0.0193 (2)
H230.04570.40990.78950.023*
C240.01229 (14)0.20659 (13)0.80953 (8)0.0215 (2)
H240.05940.19380.77170.026*
C250.05059 (14)0.09686 (12)0.85563 (8)0.0206 (2)
H250.04670.01100.84780.025*
C260.11945 (13)0.11459 (12)0.91347 (7)0.0173 (2)
H260.16020.04050.94450.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01506 (13)0.01416 (13)0.01598 (13)0.00176 (10)0.00177 (10)0.00469 (11)
P20.01608 (14)0.01828 (14)0.02113 (15)0.00210 (11)0.00139 (11)0.00833 (12)
Cl10.01584 (13)0.02787 (16)0.03554 (17)0.00389 (11)0.00692 (12)0.01626 (13)
Cl20.03337 (16)0.02003 (14)0.01712 (13)0.00576 (12)0.00743 (12)0.00241 (11)
Cl30.02375 (14)0.01470 (13)0.03347 (16)0.00319 (10)0.00717 (12)0.00981 (12)
Cl40.03023 (16)0.01762 (14)0.03012 (16)0.00014 (11)0.00303 (13)0.01181 (12)
Cl50.01465 (13)0.02888 (16)0.03224 (17)0.00367 (11)0.00517 (11)0.00237 (13)
Cl60.01801 (12)0.02041 (13)0.01493 (12)0.00326 (10)0.00044 (10)0.00574 (10)
Cl70.01931 (13)0.01662 (13)0.02051 (13)0.00006 (10)0.00840 (10)0.00040 (10)
Cl80.02391 (14)0.01671 (13)0.02950 (15)0.00085 (10)0.00885 (12)0.01059 (11)
Cl90.03447 (17)0.02083 (15)0.03949 (19)0.00828 (12)0.01166 (15)0.01450 (14)
Cl100.03997 (19)0.03674 (19)0.02181 (15)0.01409 (15)0.01217 (14)0.01051 (13)
O10.0159 (4)0.0139 (4)0.0171 (4)0.0010 (3)0.0005 (3)0.0048 (3)
O20.0265 (4)0.0188 (4)0.0171 (4)0.0011 (3)0.0040 (3)0.0038 (3)
O30.0183 (4)0.0151 (4)0.0185 (4)0.0029 (3)0.0016 (3)0.0066 (3)
O40.0269 (5)0.0413 (6)0.0406 (6)0.0166 (5)0.0146 (4)0.0219 (5)
C10.0140 (5)0.0156 (5)0.0157 (5)0.0010 (4)0.0003 (4)0.0037 (4)
C20.0149 (5)0.0149 (5)0.0122 (5)0.0005 (4)0.0027 (4)0.0035 (4)
C30.0163 (5)0.0140 (5)0.0128 (5)0.0012 (4)0.0030 (4)0.0040 (4)
C40.0147 (5)0.0187 (5)0.0144 (5)0.0002 (4)0.0033 (4)0.0050 (4)
C50.0183 (5)0.0158 (5)0.0138 (5)0.0029 (4)0.0040 (4)0.0025 (4)
C60.0203 (5)0.0136 (5)0.0155 (5)0.0027 (4)0.0060 (4)0.0045 (4)
C70.0154 (5)0.0171 (5)0.0159 (5)0.0019 (4)0.0039 (4)0.0051 (4)
C80.0112 (5)0.0153 (5)0.0179 (5)0.0016 (4)0.0034 (4)0.0058 (4)
C90.0150 (5)0.0165 (5)0.0191 (5)0.0008 (4)0.0040 (4)0.0047 (4)
C100.0171 (5)0.0247 (6)0.0183 (5)0.0004 (4)0.0061 (4)0.0056 (5)
C110.0208 (6)0.0277 (6)0.0259 (6)0.0042 (5)0.0103 (5)0.0142 (5)
C120.0263 (6)0.0179 (6)0.0345 (7)0.0017 (5)0.0138 (5)0.0114 (5)
C130.0197 (5)0.0151 (5)0.0243 (6)0.0009 (4)0.0075 (5)0.0042 (4)
C140.0138 (5)0.0140 (5)0.0134 (5)0.0000 (4)0.0027 (4)0.0023 (4)
C150.0140 (5)0.0142 (5)0.0146 (5)0.0022 (4)0.0049 (4)0.0023 (4)
C160.0161 (5)0.0149 (5)0.0157 (5)0.0006 (4)0.0048 (4)0.0051 (4)
C170.0161 (5)0.0187 (5)0.0162 (5)0.0030 (4)0.0033 (4)0.0032 (4)
C180.0187 (5)0.0158 (5)0.0189 (5)0.0039 (4)0.0073 (4)0.0025 (4)
C190.0196 (5)0.0137 (5)0.0191 (5)0.0011 (4)0.0096 (4)0.0050 (4)
C200.0161 (5)0.0170 (5)0.0159 (5)0.0004 (4)0.0061 (4)0.0044 (4)
C210.0118 (4)0.0142 (5)0.0136 (5)0.0016 (4)0.0016 (4)0.0032 (4)
C220.0175 (5)0.0125 (5)0.0168 (5)0.0001 (4)0.0039 (4)0.0040 (4)
C230.0213 (5)0.0179 (5)0.0191 (5)0.0011 (4)0.0079 (4)0.0037 (4)
C240.0244 (6)0.0227 (6)0.0204 (6)0.0030 (5)0.0089 (5)0.0076 (5)
C250.0246 (6)0.0158 (5)0.0231 (6)0.0032 (4)0.0056 (5)0.0079 (5)
C260.0197 (5)0.0128 (5)0.0185 (5)0.0002 (4)0.0050 (4)0.0027 (4)
Geometric parameters (Å, º) top
Cl6—C141.8132 (11)C8—C91.3975 (16)
P1—O21.4576 (9)C20—C151.3953 (16)
P1—O11.5830 (9)C20—C191.3974 (16)
P1—Cl41.9836 (4)C20—H200.9300
P1—Cl51.9948 (4)C7—C61.3914 (16)
Cl7—C141.8055 (12)C7—C21.3965 (16)
Cl8—C191.7431 (12)C7—H70.9300
Cl3—C61.7384 (12)C16—C171.3859 (16)
Cl1—C11.8123 (12)C16—C151.4047 (15)
Cl2—C11.8070 (12)C19—C181.3838 (17)
P2—O41.4524 (10)C13—C121.3918 (18)
P2—O31.5699 (9)C13—H130.9300
P2—Cl91.9838 (5)C22—C231.3888 (16)
P2—Cl101.9917 (5)C22—C211.4028 (16)
O1—C31.4080 (13)C22—H220.9300
O3—C161.4078 (14)C23—C241.3976 (17)
C14—C211.5241 (16)C23—H230.9300
C14—C151.5325 (15)C24—C251.3916 (18)
C5—C61.3892 (16)C24—H240.9300
C5—C41.3904 (16)C18—C171.3936 (17)
C5—H50.9300C18—H180.9300
C3—C41.3826 (16)C17—H170.9300
C3—C21.4042 (15)C9—C101.3877 (17)
C1—C81.5206 (16)C9—H90.9300
C1—C21.5245 (15)C12—C111.390 (2)
C26—C211.3919 (15)C12—H120.9300
C26—C251.3955 (17)C11—C101.3897 (18)
C26—H260.9300C11—H110.9300
C4—H40.9300C10—H100.9300
C8—C131.3963 (16)C25—H250.9300
O2—P1—O1117.54 (5)C3—C2—C1119.83 (10)
O2—P1—Cl4115.69 (4)C17—C16—C15122.46 (11)
O1—P1—Cl4100.43 (3)C17—C16—O3121.15 (10)
O2—P1—Cl5112.58 (4)C15—C16—O3116.22 (10)
O1—P1—Cl5104.90 (4)C20—C15—C16117.56 (10)
Cl4—P1—Cl5104.02 (2)C20—C15—C14122.84 (10)
O4—P2—O3118.43 (6)C16—C15—C14119.60 (10)
O4—P2—Cl9114.03 (5)C18—C19—C20121.67 (11)
O3—P2—Cl999.59 (4)C18—C19—Cl8119.86 (9)
O4—P2—Cl10113.31 (6)C20—C19—Cl8118.47 (9)
O3—P2—Cl10105.19 (4)C12—C13—C8119.94 (12)
Cl9—P2—Cl10104.54 (2)C12—C13—H13120.0
C3—O1—P1122.67 (7)C8—C13—H13120.0
C16—O3—P2127.64 (8)C23—C22—C21120.57 (10)
C21—C14—C15113.26 (9)C23—C22—H22119.7
C21—C14—Cl7112.89 (8)C21—C22—H22119.7
C15—C14—Cl7108.10 (8)C22—C23—C24119.82 (11)
C21—C14—Cl6106.40 (7)C22—C23—H23120.1
C15—C14—Cl6110.76 (8)C24—C23—H23120.1
Cl7—C14—Cl6105.13 (6)C25—C24—C23119.69 (11)
C6—C5—C4118.41 (11)C25—C24—H24120.2
C6—C5—H5120.8C23—C24—H24120.2
C4—C5—H5120.8C5—C6—C7121.78 (11)
C4—C3—C2122.19 (10)C5—C6—Cl3118.99 (9)
C4—C3—O1120.55 (10)C7—C6—Cl3119.22 (9)
C2—C3—O1117.25 (10)C26—C21—C22119.43 (10)
C8—C1—C2114.14 (9)C26—C21—C14123.46 (10)
C8—C1—Cl2111.82 (8)C22—C21—C14116.95 (10)
C2—C1—Cl2107.41 (8)C19—C18—C17119.08 (11)
C8—C1—Cl1106.14 (8)C19—C18—H18120.5
C2—C1—Cl1111.62 (8)C17—C18—H18120.5
Cl2—C1—Cl1105.41 (6)C16—C17—C18119.22 (11)
C21—C26—C25119.92 (11)C16—C17—H17120.4
C21—C26—H26120.0C18—C17—H17120.4
C25—C26—H26120.0C10—C9—C8120.04 (11)
C3—C4—C5120.00 (10)C10—C9—H9120.0
C3—C4—H4120.0C8—C9—H9120.0
C5—C4—H4120.0C11—C12—C13120.37 (12)
C13—C8—C9119.56 (11)C11—C12—H12119.8
C13—C8—C1121.33 (10)C13—C12—H12119.8
C9—C8—C1118.98 (10)C10—C11—C12119.62 (12)
C15—C20—C19119.94 (11)C10—C11—H11120.2
C15—C20—H20120.0C12—C11—H11120.2
C19—C20—H20120.0C9—C10—C11120.46 (12)
C6—C7—C2120.23 (10)C9—C10—H10119.8
C6—C7—H7119.9C11—C10—H10119.8
C2—C7—H7119.9C24—C25—C26120.56 (11)
C7—C2—C3117.37 (10)C24—C25—H25119.7
C7—C2—C1122.80 (10)C26—C25—H25119.7
 

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