Crystal structures of 1-(4-chloro­phen­yl)-2-(di­phenyl­phosphor­yl)ethan-1-one and 1-(di­phenyl­phosphor­yl)-3,3-di­methyl­butan-2-one

The title compounds were synthesized via an Arbuzov reaction between an α-bromo­ketone and isopropoxydi­phenyl­phosphane. In the crystals of both compounds, mol­ecules are linked via bifurcated C—H...(O,O) hydrogen bonds, forming chains propagating along [100] and along [010].

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• R factor = 0.032
• wR factor = 0.089
• Data-to-parameter ratio = 15.2

Structure: II

• Single-crystal X-ray study
• T = 173 K
• R factor = 0.042
• wR factor = 0.118
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         33 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.979 Note
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.9 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        4.6 Ratio
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C3 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0065 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         34 Report
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         85 %

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT033_ALERT_4_G Flack x Value Deviates > 2*sigma from Zero .....      0.088 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 and SAINT (Bruker, 2013); data reduction: SAINT and XPREP (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015).

(I) 1-(4-Chlorophenyl)-2-(diphenylphosphoryl)ethan-1-one

Crystal data

C20H16ClO2P	Dx = 1.393 Mg m^−3
Mr = 354.75	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9053 reflections
a = 11.7380 (2) Å	θ = 4.4–72.0°
b = 14.4453 (3) Å	µ = 2.97 mm^−1
c = 19.9515 (3) Å	T = 173 K
V = 3382.95 (10) Å^3	Needle, colourless
Z = 8	0.36 × 0.17 × 0.13 mm
F(000) = 1472

Data collection

Bruker APEXII CCD diffractometer	2880 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 72.2°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −14→14
Tmin = 0.599, Tmax = 0.754	k = −17→17
17900 measured reflections	l = −24→23
3297 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 1.0258P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3297 reflections	Δρmax = 0.32 e Å^−3
217 parameters	Δρmin = −0.39 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.80844 (4)	0.25495 (3)	0.98830 (2)	0.04355 (14)
P1	0.47545 (3)	0.53879 (3)	0.75031 (2)	0.02092 (11)
O1	0.33462 (10)	0.47690 (9)	0.89963 (6)	0.0366 (3)
O2	0.60062 (9)	0.52376 (8)	0.75506 (6)	0.0292 (3)
C1	0.40409 (13)	0.43971 (11)	0.86325 (8)	0.0257 (3)
C2	0.38970 (12)	0.44712 (10)	0.78795 (7)	0.0243 (3)
H2A	0.3084	0.4587	0.7777	0.029*
H2B	0.4109	0.3873	0.7673	0.029*
C3	0.50328 (13)	0.38850 (10)	0.89190 (7)	0.0252 (3)
C4	0.51562 (14)	0.38806 (11)	0.96164 (8)	0.0293 (3)
H4	0.4594	0.4170	0.9887	0.035*
C5	0.60803 (15)	0.34632 (12)	0.99183 (8)	0.0328 (4)
H5	0.6163	0.3468	1.0392	0.039*
C6	0.68856 (14)	0.30356 (11)	0.95145 (9)	0.0314 (4)
C7	0.67686 (14)	0.30005 (12)	0.88247 (9)	0.0324 (4)
H7	0.7316	0.2685	0.8559	0.039*
C8	0.58415 (14)	0.34315 (11)	0.85264 (8)	0.0289 (3)
H8	0.5758	0.3417	0.8053	0.035*
C9	0.42652 (13)	0.54676 (10)	0.66510 (7)	0.0236 (3)
C10	0.50496 (14)	0.57592 (12)	0.61691 (8)	0.0319 (4)
H10	0.5815	0.5886	0.6293	0.038*
C11	0.47052 (16)	0.58623 (13)	0.55074 (9)	0.0391 (4)
H11	0.5234	0.6071	0.5180	0.047*
C12	0.35988 (17)	0.56633 (13)	0.53235 (8)	0.0384 (4)
H12	0.3372	0.5726	0.4869	0.046*
C13	0.28230 (15)	0.53745 (12)	0.57968 (9)	0.0347 (4)
H13	0.2063	0.5238	0.5667	0.042*
C14	0.31441 (13)	0.52817 (11)	0.64629 (8)	0.0283 (3)
H14	0.2603	0.5092	0.6789	0.034*
C15	0.43163 (12)	0.64440 (10)	0.79158 (7)	0.0230 (3)
C16	0.51476 (14)	0.70315 (11)	0.81674 (8)	0.0290 (3)
H16	0.5927	0.6859	0.8143	0.035*
C17	0.48423 (15)	0.78728 (12)	0.84549 (8)	0.0338 (4)
H17	0.5413	0.8276	0.8624	0.041*
C18	0.37069 (16)	0.81216 (12)	0.84948 (8)	0.0345 (4)
H18	0.3498	0.8701	0.8683	0.041*
C19	0.28765 (15)	0.75256 (12)	0.82598 (9)	0.0345 (4)
H19	0.2097	0.7692	0.8299	0.041*
C20	0.31663 (13)	0.66892 (11)	0.79674 (8)	0.0286 (3)
H20	0.2591	0.6286	0.7803	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0357 (2)	0.0428 (3)	0.0521 (3)	0.00128 (18)	−0.01410 (19)	0.00816 (19)
P1	0.0163 (2)	0.0199 (2)	0.0265 (2)	−0.00157 (13)	−0.00033 (13)	−0.00008 (13)
O1	0.0337 (6)	0.0397 (7)	0.0364 (6)	0.0080 (5)	0.0075 (5)	−0.0014 (5)
O2	0.0181 (5)	0.0310 (6)	0.0386 (6)	−0.0002 (5)	−0.0015 (4)	0.0010 (5)
C1	0.0251 (7)	0.0207 (7)	0.0311 (8)	−0.0041 (6)	0.0033 (6)	−0.0002 (6)
C2	0.0215 (7)	0.0207 (7)	0.0307 (8)	−0.0029 (6)	−0.0001 (6)	0.0011 (6)
C3	0.0264 (7)	0.0203 (7)	0.0289 (7)	−0.0046 (6)	0.0017 (6)	0.0012 (6)
C4	0.0330 (8)	0.0259 (8)	0.0292 (8)	−0.0031 (7)	0.0059 (6)	0.0006 (6)
C5	0.0416 (9)	0.0299 (9)	0.0269 (8)	−0.0052 (7)	−0.0015 (7)	0.0036 (6)
C6	0.0291 (8)	0.0255 (8)	0.0395 (9)	−0.0037 (7)	−0.0057 (7)	0.0052 (7)
C7	0.0303 (8)	0.0305 (9)	0.0365 (9)	0.0029 (7)	0.0014 (7)	−0.0023 (7)
C8	0.0314 (8)	0.0279 (8)	0.0275 (7)	0.0008 (6)	−0.0002 (6)	−0.0012 (6)
C9	0.0231 (7)	0.0207 (7)	0.0269 (7)	−0.0003 (6)	0.0003 (6)	−0.0011 (5)
C10	0.0281 (8)	0.0333 (9)	0.0342 (8)	−0.0055 (7)	0.0053 (7)	−0.0028 (7)
C11	0.0454 (10)	0.0409 (10)	0.0310 (8)	−0.0048 (8)	0.0106 (7)	0.0015 (7)
C12	0.0508 (11)	0.0371 (10)	0.0273 (8)	0.0020 (8)	−0.0037 (7)	0.0012 (7)
C13	0.0328 (9)	0.0356 (10)	0.0357 (9)	−0.0013 (7)	−0.0088 (7)	−0.0015 (7)
C14	0.0241 (8)	0.0299 (8)	0.0308 (8)	−0.0027 (6)	−0.0008 (6)	0.0011 (6)
C15	0.0242 (7)	0.0207 (7)	0.0240 (7)	−0.0016 (6)	0.0001 (6)	0.0007 (5)
C16	0.0277 (8)	0.0277 (8)	0.0315 (8)	−0.0037 (6)	−0.0027 (6)	−0.0001 (6)
C17	0.0440 (9)	0.0269 (9)	0.0307 (8)	−0.0075 (7)	−0.0060 (7)	−0.0030 (6)
C18	0.0511 (10)	0.0234 (8)	0.0291 (8)	0.0056 (7)	−0.0006 (7)	−0.0021 (6)
C19	0.0341 (9)	0.0302 (9)	0.0393 (9)	0.0088 (7)	0.0007 (7)	−0.0002 (7)
C20	0.0258 (7)	0.0256 (8)	0.0345 (8)	0.0008 (6)	−0.0026 (6)	0.0008 (6)

Geometric parameters (Å, º)

Cl1—C6	1.7360 (16)	C9—C14	1.395 (2)
P1—O2	1.4882 (11)	C10—H10	0.9500
P1—C2	1.8251 (15)	C10—C11	1.389 (2)
P1—C9	1.7982 (15)	C11—H11	0.9500
P1—C15	1.8083 (15)	C11—C12	1.380 (3)
O1—C1	1.2168 (19)	C12—H12	0.9500
C1—C2	1.515 (2)	C12—C13	1.377 (3)
C1—C3	1.493 (2)	C13—H13	0.9500
C2—H2A	0.9900	C13—C14	1.388 (2)
C2—H2B	0.9900	C14—H14	0.9500
C3—C4	1.399 (2)	C15—C16	1.387 (2)
C3—C8	1.394 (2)	C15—C20	1.399 (2)
C4—H4	0.9500	C16—H16	0.9500
C4—C5	1.380 (2)	C16—C17	1.391 (2)
C5—H5	0.9500	C17—H17	0.9500
C5—C6	1.387 (2)	C17—C18	1.383 (3)
C6—C7	1.384 (2)	C18—H18	0.9500
C7—H7	0.9500	C18—C19	1.382 (3)
C7—C8	1.388 (2)	C19—H19	0.9500
C8—H8	0.9500	C19—C20	1.384 (2)
C9—C10	1.396 (2)	C20—H20	0.9500
O2—P1—C2	114.35 (7)	C14—C9—C10	119.68 (14)
O2—P1—C9	112.64 (7)	C9—C10—H10	120.2
O2—P1—C15	112.02 (7)	C11—C10—C9	119.67 (16)
C9—P1—C2	105.04 (7)	C11—C10—H10	120.2
C9—P1—C15	106.60 (7)	C10—C11—H11	119.9
C15—P1—C2	105.54 (7)	C12—C11—C10	120.30 (16)
O1—C1—C2	119.05 (14)	C12—C11—H11	119.9
O1—C1—C3	120.86 (14)	C11—C12—H12	119.9
C3—C1—C2	120.09 (13)	C13—C12—C11	120.22 (16)
P1—C2—H2A	108.9	C13—C12—H12	119.9
P1—C2—H2B	108.9	C12—C13—H13	119.8
C1—C2—P1	113.43 (10)	C12—C13—C14	120.44 (16)
C1—C2—H2A	108.9	C14—C13—H13	119.8
C1—C2—H2B	108.9	C9—C14—H14	120.2
H2A—C2—H2B	107.7	C13—C14—C9	119.69 (15)
C4—C3—C1	117.63 (14)	C13—C14—H14	120.2
C8—C3—C1	123.27 (14)	C16—C15—P1	118.74 (12)
C8—C3—C4	119.09 (15)	C16—C15—C20	119.81 (15)
C3—C4—H4	119.4	C20—C15—P1	121.42 (12)
C5—C4—C3	121.18 (15)	C15—C16—H16	119.9
C5—C4—H4	119.4	C15—C16—C17	120.17 (15)
C4—C5—H5	120.8	C17—C16—H16	119.9
C4—C5—C6	118.47 (15)	C16—C17—H17	120.0
C6—C5—H5	120.8	C18—C17—C16	119.95 (15)
C5—C6—Cl1	119.11 (13)	C18—C17—H17	120.0
C7—C6—Cl1	119.12 (13)	C17—C18—H18	120.1
C7—C6—C5	121.75 (15)	C19—C18—C17	119.88 (16)
C6—C7—H7	120.4	C19—C18—H18	120.1
C6—C7—C8	119.20 (15)	C18—C19—H19	119.6
C8—C7—H7	120.4	C18—C19—C20	120.89 (16)
C3—C8—H8	119.9	C20—C19—H19	119.6
C7—C8—C3	120.25 (15)	C15—C20—H20	120.4
C7—C8—H8	119.9	C19—C20—C15	119.27 (15)
C10—C9—P1	117.37 (12)	C19—C20—H20	120.4
C14—C9—P1	122.92 (12)
Cl1—C6—C7—C8	−176.61 (13)	C4—C5—C6—Cl1	177.30 (13)
P1—C9—C10—C11	−177.86 (13)	C4—C5—C6—C7	−1.5 (3)
P1—C9—C14—C13	178.80 (13)	C5—C6—C7—C8	2.2 (3)
P1—C15—C16—C17	176.49 (12)	C6—C7—C8—C3	−0.7 (3)
P1—C15—C20—C19	−176.96 (12)	C8—C3—C4—C5	2.2 (2)
O1—C1—C2—P1	97.28 (15)	C9—P1—C2—C1	−170.57 (11)
O1—C1—C3—C4	−2.5 (2)	C9—P1—C15—C16	−117.67 (13)
O1—C1—C3—C8	178.73 (16)	C9—P1—C15—C20	60.42 (14)
O2—P1—C2—C1	65.44 (12)	C9—C10—C11—C12	−1.1 (3)
O2—P1—C9—C10	−25.46 (15)	C10—C9—C14—C13	1.0 (2)
O2—P1—C9—C14	156.68 (13)	C10—C11—C12—C13	1.0 (3)
O2—P1—C15—C16	5.96 (14)	C11—C12—C13—C14	0.1 (3)
O2—P1—C15—C20	−175.96 (12)	C12—C13—C14—C9	−1.1 (3)
C1—C3—C4—C5	−176.70 (15)	C14—C9—C10—C11	0.1 (2)
C1—C3—C8—C7	177.34 (15)	C15—P1—C2—C1	−58.14 (12)
C2—P1—C9—C10	−150.53 (13)	C15—P1—C9—C10	97.79 (13)
C2—P1—C9—C14	31.61 (15)	C15—P1—C9—C14	−80.08 (14)
C2—P1—C15—C16	130.99 (12)	C15—C16—C17—C18	0.5 (2)
C2—P1—C15—C20	−50.92 (14)	C16—C15—C20—C19	1.1 (2)
C2—C1—C3—C4	176.67 (14)	C16—C17—C18—C19	1.2 (3)
C2—C1—C3—C8	−2.1 (2)	C17—C18—C19—C20	−1.7 (3)
C3—C1—C2—P1	−81.86 (15)	C18—C19—C20—C15	0.6 (3)
C3—C4—C5—C6	−0.7 (2)	C20—C15—C16—C17	−1.6 (2)
C4—C3—C8—C7	−1.4 (2)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg3 are the centroids of rings C3–C8 and C15–C20, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2^i	0.95	2.30	3.1899 (19)	156
C20—H20···O2^i	0.95	2.50	3.4487 (19)	176
C5—H5···Cg3^ii	0.95	3.00	3.8873 (17)	156
C13—H13···Cg1^i	0.95	2.90	3.5373 (19)	126

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

(II) 1-(Diphenylphosphoryl)-3,3-dimethylbutan-2-one

Crystal data

C18H21O2P	F(000) = 320
Mr = 300.32	Dx = 1.195 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 8.3416 (2) Å	Cell parameters from 5567 reflections
b = 10.5161 (2) Å	θ = 4.7–72.0°
c = 10.2790 (2) Å	µ = 1.47 mm^−1
β = 112.212 (1)°	T = 173 K
V = 834.77 (3) Å^3	Needle, colourless
Z = 2	0.43 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3006 independent reflections
Radiation source: sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 8 pixels mm^-1	θmax = 72.0°, θmin = 4.7°
ω and φ scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
Tmin = 0.631, Tmax = 0.754	l = −12→12
7043 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0722P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.49 e Å^−3
3006 reflections	Δρmin = −0.38 e Å^−3
193 parameters	Absolute structure: Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.088 (14)
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.46337 (9)	0.13395 (7)	0.54974 (7)	0.0247 (2)
O1	0.2783 (3)	0.1230 (4)	0.2325 (3)	0.0450 (7)
O2	0.4313 (3)	0.2739 (3)	0.5441 (3)	0.0352 (6)
C1	0.4309 (5)	0.1015 (3)	0.2672 (3)	0.0328 (8)
C2	0.5430 (4)	0.0741 (4)	0.4198 (3)	0.0286 (7)
H2A	0.6592	0.1108	0.4399	0.034*
H2B	0.5572	−0.0192	0.4317	0.034*
C3	0.5199 (5)	0.0970 (4)	0.1613 (4)	0.0403 (9)
C4	0.3850 (8)	0.0965 (11)	0.0140 (5)	0.105 (4)
H4A	0.3118	0.0210	0.0006	0.157*
H4B	0.4422	0.0952	−0.0536	0.157*
H4C	0.3133	0.1731	−0.0008	0.157*
C5	0.6294 (11)	0.2154 (7)	0.1830 (7)	0.090 (3)
H5A	0.5596	0.2900	0.1842	0.135*
H5B	0.6712	0.2237	0.1062	0.135*
H5C	0.7284	0.2094	0.2726	0.135*
C6	0.6318 (9)	−0.0220 (7)	0.1848 (6)	0.0713 (17)
H6A	0.7288	−0.0159	0.2757	0.107*
H6B	0.6765	−0.0295	0.1096	0.107*
H6C	0.5619	−0.0970	0.1842	0.107*
C7	0.6358 (4)	0.0881 (4)	0.7129 (3)	0.0280 (7)
C8	0.7278 (5)	0.1814 (4)	0.8067 (4)	0.0400 (9)
H8	0.6982	0.2684	0.7865	0.048*
C9	0.8634 (5)	0.1477 (6)	0.9304 (4)	0.0518 (12)
H9	0.9264	0.2117	0.9946	0.062*
C10	0.9069 (5)	0.0207 (5)	0.9603 (4)	0.0485 (11)
H10	0.9994	−0.0023	1.0449	0.058*
C11	0.8157 (5)	−0.0721 (5)	0.8669 (4)	0.0459 (10)
H11	0.8455	−0.1590	0.8873	0.055*
C12	0.6802 (4)	−0.0389 (4)	0.7431 (4)	0.0341 (8)
H12	0.6178	−0.1031	0.6790	0.041*
C13	0.2784 (4)	0.0408 (4)	0.5431 (3)	0.0270 (6)
C14	0.2209 (5)	−0.0666 (4)	0.4600 (4)	0.0399 (9)
H14	0.2786	−0.0945	0.4012	0.048*
C15	0.0789 (6)	−0.1332 (5)	0.4632 (5)	0.0486 (11)
H15	0.0387	−0.2059	0.4051	0.058*
C16	−0.0046 (5)	−0.0952 (5)	0.5495 (5)	0.0462 (10)
H16	−0.1014	−0.1416	0.5513	0.055*
C17	0.0532 (5)	0.0105 (4)	0.6328 (4)	0.0422 (9)
H17	−0.0035	0.0366	0.6930	0.051*
C18	0.1936 (5)	0.0793 (4)	0.6298 (4)	0.0337 (7)
H18	0.2320	0.1528	0.6870	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0238 (4)	0.0270 (4)	0.0251 (3)	−0.0011 (3)	0.0113 (3)	0.0003 (3)
O1	0.0312 (12)	0.068 (2)	0.0324 (11)	0.0044 (14)	0.0085 (10)	0.0033 (14)
O2	0.0398 (13)	0.0270 (14)	0.0428 (14)	0.0012 (10)	0.0200 (11)	0.0020 (10)
C1	0.0345 (17)	0.037 (2)	0.0268 (15)	−0.0019 (13)	0.0119 (13)	−0.0008 (13)
C2	0.0276 (15)	0.0364 (18)	0.0257 (15)	0.0004 (13)	0.0143 (12)	−0.0003 (13)
C3	0.043 (2)	0.054 (3)	0.0278 (16)	0.0021 (17)	0.0182 (16)	0.0016 (15)
C4	0.068 (3)	0.218 (12)	0.027 (2)	0.022 (5)	0.018 (2)	−0.004 (4)
C5	0.138 (6)	0.084 (5)	0.094 (5)	−0.045 (5)	0.096 (5)	−0.025 (4)
C6	0.092 (4)	0.080 (4)	0.067 (3)	0.029 (3)	0.059 (3)	0.011 (3)
C7	0.0222 (13)	0.0427 (18)	0.0212 (14)	−0.0043 (13)	0.0106 (12)	−0.0009 (12)
C8	0.0411 (19)	0.047 (2)	0.0348 (19)	−0.0138 (17)	0.0173 (16)	−0.0079 (15)
C9	0.0411 (19)	0.079 (3)	0.0333 (17)	−0.027 (2)	0.0120 (15)	−0.016 (2)
C10	0.0291 (17)	0.083 (3)	0.0281 (17)	−0.006 (2)	0.0045 (14)	0.0044 (19)
C11	0.0315 (18)	0.063 (3)	0.038 (2)	0.0070 (18)	0.0082 (16)	0.0108 (19)
C12	0.0267 (16)	0.043 (2)	0.0292 (17)	−0.0013 (14)	0.0066 (14)	0.0005 (14)
C13	0.0200 (13)	0.0328 (16)	0.0276 (15)	0.0006 (12)	0.0083 (12)	0.0047 (13)
C14	0.0336 (18)	0.042 (2)	0.047 (2)	−0.0061 (16)	0.0181 (17)	−0.0107 (16)
C15	0.0392 (19)	0.041 (3)	0.065 (3)	−0.012 (2)	0.019 (2)	−0.0121 (19)
C16	0.0262 (16)	0.052 (2)	0.062 (3)	−0.0053 (18)	0.0184 (18)	0.011 (2)
C17	0.0314 (17)	0.057 (3)	0.044 (2)	0.0000 (17)	0.0216 (16)	0.0036 (18)
C18	0.0292 (16)	0.0431 (19)	0.0306 (16)	0.0007 (15)	0.0133 (14)	−0.0011 (14)

Geometric parameters (Å, º)

P1—O2	1.493 (3)	C7—C12	1.389 (6)
P1—C2	1.814 (3)	C8—H8	0.9500
P1—C7	1.814 (3)	C8—C9	1.391 (6)
P1—C13	1.807 (3)	C9—H9	0.9500
O1—C1	1.207 (5)	C9—C10	1.387 (8)
C1—C2	1.520 (5)	C10—H10	0.9500
C1—C3	1.533 (5)	C10—C11	1.378 (7)
C2—H2A	0.9900	C11—H11	0.9500
C2—H2B	0.9900	C11—C12	1.390 (5)
C3—C4	1.507 (6)	C12—H12	0.9500
C3—C5	1.509 (7)	C13—C14	1.388 (6)
C3—C6	1.525 (7)	C13—C18	1.391 (5)
C4—H4A	0.9800	C14—H14	0.9500
C4—H4B	0.9800	C14—C15	1.387 (6)
C4—H4C	0.9800	C15—H15	0.9500
C5—H5A	0.9800	C15—C16	1.378 (7)
C5—H5B	0.9800	C16—H16	0.9500
C5—H5C	0.9800	C16—C17	1.375 (7)
C6—H6A	0.9800	C17—H17	0.9500
C6—H6B	0.9800	C17—C18	1.387 (5)
C6—H6C	0.9800	C18—H18	0.9500
C7—C8	1.387 (5)
O2—P1—C2	115.06 (16)	H6B—C6—H6C	109.5
O2—P1—C7	111.47 (16)	C8—C7—P1	119.5 (3)
O2—P1—C13	113.25 (15)	C8—C7—C12	119.6 (3)
C7—P1—C2	101.84 (15)	C12—C7—P1	120.9 (3)
C13—P1—C2	109.21 (16)	C7—C8—H8	120.0
C13—P1—C7	104.98 (16)	C7—C8—C9	120.0 (4)
O1—C1—C2	120.6 (3)	C9—C8—H8	120.0
O1—C1—C3	122.4 (3)	C8—C9—H9	119.9
C2—C1—C3	117.0 (3)	C10—C9—C8	120.1 (4)
P1—C2—H2A	108.3	C10—C9—H9	119.9
P1—C2—H2B	108.3	C9—C10—H10	120.1
C1—C2—P1	116.1 (2)	C11—C10—C9	119.9 (4)
C1—C2—H2A	108.3	C11—C10—H10	120.1
C1—C2—H2B	108.3	C10—C11—H11	119.9
H2A—C2—H2B	107.4	C10—C11—C12	120.2 (4)
C4—C3—C1	109.6 (4)	C12—C11—H11	119.9
C4—C3—C5	109.4 (6)	C7—C12—C11	120.1 (4)
C4—C3—C6	109.7 (5)	C7—C12—H12	119.9
C5—C3—C1	107.3 (3)	C11—C12—H12	119.9
C5—C3—C6	110.7 (5)	C14—C13—P1	123.8 (3)
C6—C3—C1	110.1 (4)	C14—C13—C18	119.4 (3)
C3—C4—H4A	109.5	C18—C13—P1	116.8 (3)
C3—C4—H4B	109.5	C13—C14—H14	120.1
C3—C4—H4C	109.5	C15—C14—C13	119.7 (4)
H4A—C4—H4B	109.5	C15—C14—H14	120.1
H4A—C4—H4C	109.5	C14—C15—H15	119.6
H4B—C4—H4C	109.5	C16—C15—C14	120.8 (4)
C3—C5—H5A	109.5	C16—C15—H15	119.6
C3—C5—H5B	109.5	C15—C16—H16	120.3
C3—C5—H5C	109.5	C17—C16—C15	119.5 (4)
H5A—C5—H5B	109.5	C17—C16—H16	120.3
H5A—C5—H5C	109.5	C16—C17—H17	119.7
H5B—C5—H5C	109.5	C16—C17—C18	120.6 (4)
C3—C6—H6A	109.5	C18—C17—H17	119.7
C3—C6—H6B	109.5	C13—C18—H18	120.0
C3—C6—H6C	109.5	C17—C18—C13	120.0 (4)
H6A—C6—H6B	109.5	C17—C18—H18	120.0
H6A—C6—H6C	109.5
P1—C7—C8—C9	−178.3 (3)	C3—C1—C2—P1	158.4 (3)
P1—C7—C12—C11	178.3 (3)	C7—P1—C2—C1	−177.5 (3)
P1—C13—C14—C15	179.1 (3)	C7—P1—C13—C14	−102.8 (3)
P1—C13—C18—C17	−178.4 (3)	C7—P1—C13—C18	75.6 (3)
O1—C1—C2—P1	−23.1 (5)	C7—C8—C9—C10	0.0 (6)
O1—C1—C3—C4	−11.3 (7)	C8—C7—C12—C11	0.3 (5)
O1—C1—C3—C5	107.4 (6)	C8—C9—C10—C11	0.1 (6)
O1—C1—C3—C6	−132.0 (5)	C9—C10—C11—C12	−0.1 (6)
O2—P1—C2—C1	−56.8 (3)	C10—C11—C12—C7	−0.1 (6)
O2—P1—C7—C8	−5.5 (3)	C12—C7—C8—C9	−0.2 (5)
O2—P1—C7—C12	176.4 (3)	C13—P1—C2—C1	71.8 (3)
O2—P1—C13—C14	135.4 (3)	C13—P1—C7—C8	−128.5 (3)
O2—P1—C13—C18	−46.2 (3)	C13—P1—C7—C12	53.5 (3)
C2—P1—C7—C8	117.7 (3)	C13—C14—C15—C16	−1.0 (7)
C2—P1—C7—C12	−60.4 (3)	C14—C13—C18—C17	0.0 (6)
C2—P1—C13—C14	5.8 (4)	C14—C15—C16—C17	0.3 (7)
C2—P1—C13—C18	−175.8 (3)	C15—C16—C17—C18	0.5 (7)
C2—C1—C3—C4	167.2 (5)	C16—C17—C18—C13	−0.7 (6)
C2—C1—C3—C5	−74.1 (5)	C18—C13—C14—C15	0.8 (6)
C2—C1—C3—C6	46.5 (5)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of ring C7–C12.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2^i	0.99	2.19	3.176 (5)	176
C12—H12···O2^i	0.95	2.53	3.373 (5)	148
C17—H17···Cg1^ii	0.95	2.80	3.721 (5)	164

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