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In the title compound, C20H16BrClNO2PS, the six-membered oxaza­phosphinine ring exhibits a boat conformation, with the S atom in an axial position. The methoxy­phenyl and chloro­benzene groups are trans to each othe. The structure is stabilized by inter­molecular C—H...S hydrogen bonds, linking the mol­ecules into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701776X/rz2131sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701776X/rz2131Isup2.hkl
Contains datablock I

CCDC reference: 647315

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEPII (Zsolnai, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).

6-Bromo-3-(4-chlorophenyl)-2-(4-methoxyphenyl)- 3,4-dihydro-1,3,2-benzoxazaphosphinine 2-sulfide top
Crystal data top
C20H16BrClNO2PSF(000) = 968
Mr = 480.73Dx = 1.586 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 898 reflections
a = 8.7765 (10) Åθ = 2.2–25.0°
b = 10.1549 (12) ŵ = 2.37 mm1
c = 22.707 (3) ÅT = 293 K
β = 95.885 (2)°Prism, white
V = 2013.1 (4) Å30.24 × 0.24 × 0.13 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
3543 independent reflections
Radiation source: fine-focus sealed tube2775 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.588, Tmax = 0.731k = 1212
18958 measured reflectionsl = 2726
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0704P)2 + 1.7985P]
where P = (Fo2 + 2Fc2)/3
3543 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 1.40 e Å3
0 restraintsΔρmin = 0.73 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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = 0.94956(0.00059) m2 = 0.31103(0.00178) m3 = -0.03982(0.00098) D = 2.01109(0.00459) Atom d s d/s (d/s)**2 P1 * -0.0013 0.0009 - 1.415 2.002 N5 * 0.0149 0.0030 4.974 24.738 C17 * -0.0252 0.0035 - 7.101 50.421 C12 * 0.0231 0.0035 6.686 44.697 C18 0.5165 0.0038 135.962 18485.555 O3 0.5914 0.0025 240.524 57851.988 ============ Sum((d/s)**2) for starred atoms 121.858 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity

Plane 2 m1 = 0.96646(0.00033) m2 = 0.22178(0.00132) m3 = -0.12946(0.00089) D = 1.69026(0.00428) Atom d s d/s (d/s)**2 P1 * -0.0320 0.0009 - 36.095 1302.868 N5 * 0.0345 0.0030 11.514 132.582 C17 * -0.3090 0.0035 - 87.328 7626.171 C12 * -0.3133 0.0034 - 90.913 8265.249 C18 * 0.4031 0.0038 106.262 11291.619 O3 * 0.3641 0.0025 147.683 21810.215 ============ Sum((d/s)**2) for starred atoms 50428.703 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity

Plane 3 m1 = -0.82271(0.00080) m2 = -0.43779(0.00153) m3 = -0.36261(0.00048) D = -4.54452(0.00475) Atom d s d/s (d/s)**2 C12 * 0.0242 0.0035 7.001 49.015 C13 * 0.0092 0.0039 2.351 5.526 C14 * -0.0333 0.0043 - 7.812 61.029 C15 * -0.0418 0.0041 - 10.162 103.269 C16 * -0.0274 0.0040 - 6.834 46.705 C17 * 0.0066 0.0036 1.858 3.454 Br26 * 0.0010 0.0006 1.717 2.947 ============ Sum((d/s)**2) for starred atoms 271.944 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity

Plane 4 m1 = -0.09860(0.00137) m2 = -0.88456(0.00082) m3 = -0.45588(0.00142) D = -2.27969(0.00734) Atom d s d/s (d/s)**2 C6 * 0.0021 0.0036 0.576 0.332 C7 * 0.0006 0.0044 0.144 0.021 C8 * -0.0027 0.0048 - 0.560 0.313 C9 * -0.0027 0.0041 - 0.660 0.436 C10 * -0.0021 0.0050 - 0.417 0.174 C11 * -0.0012 0.0048 - 0.255 0.065 O4 * 0.0028 0.0033 0.842 0.708 C25 * -0.0012 0.0062 - 0.201 0.040 ============ Sum((d/s)**2) for starred atoms 2.090 Chi-squared at 95% for 5 degrees of freedom: 11.10 The group of atoms does not deviate significantly from planarity

Plane 5 m1 = -0.77601(0.00086) m2 = 0.44397(0.00050) m3 = -0.44800(0.00135) D = -4.68147(0.00513) Atom d s d/s (d/s)**2 C19 * -0.0183 0.0034 - 5.328 28.392 C20 * -0.0046 0.0040 - 1.158 1.341 C21 * 0.0189 0.0042 4.503 20.275 C22 * 0.0305 0.0040 7.619 58.055 C23 * 0.0099 0.0041 2.427 5.891 C24 * 0.0028 0.0038 0.744 0.554 Cl27 * -0.0032 0.0013 - 2.494 6.220 ============ Sum((d/s)**2) for starred atoms 120.728 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 7.32 (0.10) 172.68 (0.10) 1 3 25.45 (0.07) 154.55 (0.07) 1 4 69.48 (0.11) 110.52 (0.11) 1 5 54.48 (0.09) 125.52 (0.09) 2 3 32.30 (0.07) 147.70 (0.07) 2 4 76.56 (0.11) 103.44 (0.11) 2 5 53.59 (0.09) 126.41 (0.09) 3 4 50.68 (0.11) 129.32 (0.11) 3 5 52.66 (0.09) 127.34 (0.09) 4 5 83.57 (0.09) 96.43 (0.09)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br260.17792 (7)0.06566 (6)0.47281 (2)0.0836 (2)
P10.29439 (10)0.03359 (9)0.17673 (4)0.0410 (2)
S20.08073 (10)0.02314 (10)0.14719 (5)0.0537 (3)
Cl270.09865 (15)0.62080 (11)0.14604 (6)0.0812 (4)
O30.3399 (3)0.1485 (2)0.22477 (11)0.0458 (6)
O40.7010 (3)0.1901 (3)0.00369 (13)0.0716 (9)
N50.3610 (3)0.0990 (3)0.21532 (13)0.0456 (7)
C120.3000 (4)0.1307 (3)0.28257 (15)0.0424 (8)
C60.4183 (4)0.0763 (3)0.12219 (16)0.0444 (8)
C70.5731 (4)0.0508 (4)0.13178 (18)0.0586 (11)
H70.61230.00820.16630.070*
C170.3485 (4)0.0157 (4)0.31110 (16)0.0440 (8)
C90.6162 (4)0.1504 (4)0.03956 (17)0.0525 (9)
C210.2625 (5)0.4005 (4)0.12862 (18)0.0564 (10)
H210.28110.43720.09250.068*
C130.2199 (4)0.2272 (4)0.30874 (18)0.0525 (9)
H130.18840.30340.28820.063*
C80.6712 (5)0.0880 (5)0.09050 (19)0.0650 (12)
H80.77540.07020.09770.078*
C220.1720 (4)0.4658 (4)0.16594 (19)0.0529 (10)
C190.2982 (4)0.2242 (3)0.19944 (15)0.0413 (8)
C230.1447 (5)0.4132 (4)0.21936 (19)0.0550 (10)
H230.08550.45860.24430.066*
C160.3144 (5)0.0026 (4)0.36873 (17)0.0523 (9)
H160.34520.07890.38930.063*
C150.2336 (5)0.0942 (4)0.39528 (17)0.0538 (10)
C240.2066 (4)0.2911 (4)0.23573 (17)0.0505 (9)
H240.18630.25370.27150.061*
C200.3245 (5)0.2795 (4)0.14623 (17)0.0532 (9)
H200.38520.23490.12150.064*
C180.4364 (4)0.0790 (4)0.27644 (16)0.0494 (9)
H18A0.53920.04540.27440.059*
H18B0.44470.16300.29680.059*
C140.1876 (5)0.2076 (4)0.36653 (18)0.0586 (10)
H140.13480.27140.38570.070*
C100.4605 (5)0.1763 (5)0.02979 (19)0.0703 (13)
H100.42150.21880.00480.084*
C110.3633 (5)0.1397 (5)0.07065 (19)0.0652 (12)
H110.25930.15800.06350.078*
C250.8597 (5)0.1672 (6)0.0035 (2)0.0861 (16)
H25A0.90460.20000.03050.129*
H25B0.87860.07440.00740.129*
H25C0.90430.21170.03840.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br260.1111 (5)0.0933 (4)0.0499 (3)0.0206 (3)0.0244 (3)0.0031 (2)
P10.0409 (5)0.0414 (5)0.0399 (5)0.0017 (4)0.0005 (4)0.0013 (4)
S20.0395 (5)0.0577 (6)0.0622 (6)0.0020 (4)0.0023 (4)0.0043 (5)
Cl270.0857 (8)0.0445 (6)0.1075 (10)0.0048 (5)0.0185 (7)0.0064 (6)
O30.0539 (14)0.0410 (13)0.0426 (13)0.0077 (11)0.0060 (11)0.0012 (11)
O40.0584 (18)0.100 (2)0.0578 (18)0.0053 (16)0.0151 (14)0.0215 (17)
N50.0502 (17)0.0458 (17)0.0394 (16)0.0003 (14)0.0021 (13)0.0026 (13)
C120.0440 (19)0.043 (2)0.0395 (19)0.0084 (16)0.0020 (15)0.0012 (15)
C60.046 (2)0.046 (2)0.0404 (19)0.0001 (16)0.0016 (16)0.0003 (15)
C70.047 (2)0.083 (3)0.045 (2)0.006 (2)0.0005 (17)0.018 (2)
C170.0442 (19)0.044 (2)0.042 (2)0.0061 (16)0.0050 (15)0.0025 (16)
C90.051 (2)0.061 (2)0.046 (2)0.0029 (18)0.0092 (18)0.0020 (19)
C210.073 (3)0.052 (2)0.043 (2)0.007 (2)0.0013 (19)0.0076 (18)
C130.059 (2)0.043 (2)0.056 (2)0.0014 (17)0.0048 (18)0.0019 (17)
C80.040 (2)0.098 (3)0.056 (3)0.008 (2)0.0033 (18)0.017 (2)
C220.051 (2)0.039 (2)0.065 (3)0.0041 (17)0.0106 (19)0.0015 (18)
C190.0434 (19)0.0423 (19)0.0373 (18)0.0066 (15)0.0003 (15)0.0011 (15)
C230.053 (2)0.049 (2)0.064 (3)0.0008 (18)0.0122 (19)0.011 (2)
C160.063 (2)0.048 (2)0.044 (2)0.0098 (18)0.0044 (18)0.0035 (17)
C150.063 (2)0.058 (2)0.041 (2)0.016 (2)0.0094 (18)0.0067 (18)
C240.057 (2)0.048 (2)0.048 (2)0.0070 (18)0.0133 (18)0.0004 (17)
C200.060 (2)0.055 (2)0.046 (2)0.0000 (19)0.0104 (18)0.0033 (18)
C180.048 (2)0.052 (2)0.046 (2)0.0038 (17)0.0057 (17)0.0015 (17)
C140.069 (3)0.054 (2)0.054 (2)0.002 (2)0.013 (2)0.010 (2)
C100.061 (3)0.100 (4)0.050 (2)0.015 (2)0.006 (2)0.028 (2)
C110.047 (2)0.092 (3)0.056 (2)0.014 (2)0.0030 (19)0.020 (2)
C250.061 (3)0.129 (5)0.072 (3)0.002 (3)0.024 (2)0.017 (3)
Geometric parameters (Å, º) top
Br26—C151.897 (4)C21—H210.9300
P1—O31.619 (3)C13—C141.385 (6)
P1—N51.678 (3)C13—H130.9300
P1—C61.784 (4)C8—H80.9300
P1—S21.9287 (13)C22—C231.369 (6)
Cl27—C221.743 (4)C19—C201.373 (5)
O3—C121.404 (4)C19—C241.387 (5)
O4—C91.353 (5)C23—C241.389 (5)
O4—C251.405 (5)C23—H230.9300
N5—C191.417 (5)C16—C151.386 (6)
N5—C181.489 (5)C16—H160.9300
C12—C131.376 (5)C15—C141.364 (6)
C12—C171.381 (5)C24—H240.9300
C6—C71.378 (5)C20—H200.9300
C6—C111.379 (5)C18—H18A0.9700
C7—C81.388 (6)C18—H18B0.9700
C7—H70.9300C14—H140.9300
C17—C161.384 (5)C10—C111.374 (6)
C17—C181.505 (5)C10—H100.9300
C9—C81.363 (6)C11—H110.9300
C9—C101.387 (6)C25—H25A0.9600
C21—C201.386 (6)C25—H25B0.9600
C21—C221.388 (6)C25—H25C0.9600
O3—P1—N5100.24 (14)C20—C19—N5119.7 (3)
O3—P1—C699.60 (15)C24—C19—N5121.5 (3)
N5—P1—C6110.68 (16)C22—C23—C24119.1 (4)
O3—P1—S2115.96 (11)C22—C23—H23120.5
N5—P1—S2114.30 (12)C24—C23—H23120.5
C6—P1—S2114.34 (13)C17—C16—C15119.1 (4)
C12—O3—P1118.0 (2)C17—C16—H16120.5
C9—O4—C25118.7 (3)C15—C16—H16120.5
C19—N5—C18118.9 (3)C14—C15—C16122.0 (4)
C19—N5—P1118.8 (2)C14—C15—Br26118.8 (3)
C18—N5—P1118.4 (2)C16—C15—Br26119.2 (3)
C13—C12—C17123.1 (3)C19—C24—C23120.9 (4)
C13—C12—O3119.9 (3)C19—C24—H24119.6
C17—C12—O3117.0 (3)C23—C24—H24119.6
C7—C6—C11118.4 (4)C19—C20—C21121.3 (4)
C7—C6—P1120.4 (3)C19—C20—H20119.3
C11—C6—P1121.2 (3)C21—C20—H20119.3
C6—C7—C8120.8 (4)N5—C18—C17111.8 (3)
C6—C7—H7119.6N5—C18—H18A109.3
C8—C7—H7119.6C17—C18—H18A109.3
C12—C17—C16118.1 (3)N5—C18—H18B109.3
C12—C17—C18116.4 (3)C17—C18—H18B109.3
C16—C17—C18125.5 (3)H18A—C18—H18B107.9
O4—C9—C8125.5 (4)C15—C14—C13119.7 (4)
O4—C9—C10115.7 (3)C15—C14—H14120.1
C8—C9—C10118.8 (4)C13—C14—H14120.1
C20—C21—C22118.7 (4)C11—C10—C9120.7 (4)
C20—C21—H21120.7C11—C10—H10119.7
C22—C21—H21120.7C9—C10—H10119.7
C12—C13—C14118.0 (4)C10—C11—C6120.8 (4)
C12—C13—H13121.0C10—C11—H11119.6
C14—C13—H13121.0C6—C11—H11119.6
C9—C8—C7120.6 (4)O4—C25—H25A109.5
C9—C8—H8119.7O4—C25—H25B109.5
C7—C8—H8119.7H25A—C25—H25B109.5
C23—C22—C21121.2 (4)O4—C25—H25C109.5
C23—C22—Cl27119.2 (3)H25A—C25—H25C109.5
C21—C22—Cl27119.5 (3)H25B—C25—H25C109.5
C20—C19—C24118.8 (3)
N5—P1—O3—C1249.2 (3)C20—C21—C22—C230.4 (6)
C6—P1—O3—C12162.4 (2)C20—C21—C22—Cl27177.6 (3)
S2—P1—O3—C1274.4 (2)C18—N5—C19—C20135.0 (4)
O3—P1—N5—C19157.1 (3)P1—N5—C19—C2067.7 (4)
C6—P1—N5—C1998.4 (3)C18—N5—C19—C2447.0 (5)
S2—P1—N5—C1932.4 (3)P1—N5—C19—C24110.3 (3)
O3—P1—N5—C180.2 (3)C21—C22—C23—C241.2 (6)
C6—P1—N5—C18104.2 (3)Cl27—C22—C23—C24178.4 (3)
S2—P1—N5—C18125.0 (3)C12—C17—C16—C150.0 (5)
P1—O3—C12—C13127.8 (3)C18—C17—C16—C15179.3 (4)
P1—O3—C12—C1754.0 (4)C17—C16—C15—C140.5 (6)
O3—P1—C6—C774.6 (3)C17—C16—C15—Br26176.9 (3)
N5—P1—C6—C730.3 (4)C20—C19—C24—C231.3 (6)
S2—P1—C6—C7161.1 (3)N5—C19—C24—C23179.4 (3)
O3—P1—C6—C11103.0 (4)C22—C23—C24—C191.7 (6)
N5—P1—C6—C11152.2 (3)C24—C19—C20—C210.5 (6)
S2—P1—C6—C1121.3 (4)N5—C19—C20—C21178.6 (3)
C11—C6—C7—C80.1 (7)C22—C21—C20—C190.1 (6)
P1—C6—C7—C8177.7 (3)C19—N5—C18—C17113.2 (4)
C13—C12—C17—C160.0 (5)P1—N5—C18—C1744.2 (4)
O3—C12—C17—C16178.2 (3)C12—C17—C18—N546.4 (4)
C13—C12—C17—C18179.3 (3)C16—C17—C18—N5134.4 (4)
O3—C12—C17—C181.1 (5)C16—C15—C14—C130.9 (6)
C25—O4—C9—C80.5 (7)Br26—C15—C14—C13176.5 (3)
C25—O4—C9—C10179.8 (5)C12—C13—C14—C150.8 (6)
C17—C12—C13—C140.4 (6)O4—C9—C10—C11179.7 (4)
O3—C12—C13—C14177.8 (3)C8—C9—C10—C110.0 (7)
O4—C9—C8—C7179.6 (4)C9—C10—C11—C60.1 (8)
C10—C9—C8—C70.1 (7)C7—C6—C11—C100.2 (7)
C6—C7—C8—C90.1 (7)P1—C6—C11—C10177.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···S2i0.932.843.750 (5)167
Symmetry code: (i) x+1, y, z.
 

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