Tris(1-naphth­yl) phosphite

The title compound, C₃₀H₂₁O₃P, has a distorted trigonal–pyramidal geometry around the P atom. The P—O bond lengths are between 1.609 (1) and 1.643 (1) Å, and O—P—O bond angles vary between 94.73 (5) and 101.91 (6)°. The crystal structure is stablized by weak π—π and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.106
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   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

   2 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

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97.

Tris(1-naphthyl) phosphite

Crystal data

C30H21O3P	Z = 2
Mr = 460.44	F(000) = 480
Triclinic, P1	Dx = 1.363 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5057 (2) Å	Cell parameters from 5337 reflections
b = 10.8272 (4) Å	θ = 2.3–28.3°
c = 14.6167 (5) Å	µ = 0.15 mm^−1
α = 106.782 (2)°	T = 100 K
β = 97.780 (2)°	Block, colourless
γ = 92.890 (1)°	0.24 × 0.12 × 0.10 mm
V = 1121.75 (6) Å^3

Data collection

Bruker X8 APEXII diffractometer	5403 independent reflections
Radiation source: fine-focus sealed tube	4452 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 512 pixels mm^-1	θmax = 28.0°, θmin = 2.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −14→14
Tmin = 0.964, Tmax = 0.985	l = −19→19
19931 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.4566P] where P = (Fo^2 + 2Fc^2)/3
5403 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Experimental. Spectroscopic data: ¹H NMR (CDCl₃, 300.1 MHz): δ 7.50 (s, 1H), 7.52 (s, 2H), 7.59 (dt, 1H), 7.80 (dd, 1H), 7.98 (d, 1H), 8.43 (d, 1H); ³¹P NMR ((CD₃)₂CO, 121.4 MHz): δ 130.7.

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 (Ų)

	x	y	z	Uiso*/Ueq
P	0.20126 (5)	0.62334 (4)	0.18790 (3)	0.01547 (10)
O1	0.38719 (14)	0.55003 (10)	0.17832 (7)	0.0170 (2)
O2	0.22280 (14)	0.65535 (10)	0.30562 (7)	0.0171 (2)
O3	0.27689 (13)	0.75907 (10)	0.17675 (7)	0.0161 (2)
C11	0.3803 (2)	0.41869 (14)	0.17032 (10)	0.0156 (3)
C12	0.52499 (19)	0.35270 (14)	0.13158 (10)	0.0152 (3)
C13	0.6688 (2)	0.41668 (15)	0.10347 (10)	0.0173 (3)
H13	0.6704	0.5067	0.1102	0.021*
C14	0.8051 (2)	0.34810 (16)	0.06664 (11)	0.0207 (3)
H14	0.9009	0.3910	0.0478	0.025*
C15	0.8043 (2)	0.21501 (16)	0.05652 (11)	0.0230 (3)
H15	0.8998	0.1690	0.0310	0.028*
C16	0.6676 (2)	0.15085 (16)	0.08287 (11)	0.0207 (3)
H16	0.6687	0.0608	0.0753	0.025*
C17	0.5241 (2)	0.21812 (15)	0.12147 (10)	0.0171 (3)
C18	0.3808 (2)	0.15365 (15)	0.14905 (11)	0.0203 (3)
H18	0.3794	0.0635	0.1418	0.024*
C19	0.2450 (2)	0.22087 (15)	0.18594 (11)	0.0216 (3)
H19	0.1494	0.1769	0.2041	0.026*
C110	0.2441 (2)	0.35488 (15)	0.19756 (11)	0.0196 (3)
H110	0.1494	0.4007	0.2242	0.024*
C21	0.0805 (2)	0.67074 (14)	0.35833 (10)	0.0149 (3)
C22	0.12295 (19)	0.65795 (14)	0.45288 (10)	0.0147 (3)
C23	0.2957 (2)	0.62959 (14)	0.48984 (11)	0.0182 (3)
H23	0.3886	0.6175	0.4508	0.022*
C24	0.3286 (2)	0.61969 (16)	0.58180 (12)	0.0230 (3)
H24	0.4449	0.6015	0.6064	0.028*
C25	0.1922 (2)	0.63610 (15)	0.64034 (11)	0.0232 (3)
H25	0.2166	0.6287	0.7039	0.028*
C26	0.0248 (2)	0.66264 (15)	0.60574 (11)	0.0205 (3)
H26	−0.0666	0.6729	0.6457	0.025*
C27	−0.0151 (2)	0.67516 (14)	0.51161 (10)	0.0160 (3)
C28	−0.1879 (2)	0.70372 (15)	0.47510 (11)	0.0200 (3)
H28	−0.2802	0.7156	0.5146	0.024*
C29	−0.2228 (2)	0.71431 (16)	0.38363 (12)	0.0215 (3)
H29	−0.3395	0.7324	0.3597	0.026*
C210	−0.0868 (2)	0.69869 (15)	0.32426 (11)	0.0183 (3)
H210	−0.1114	0.7075	0.2611	0.022*
C31	0.40992 (19)	0.85082 (14)	0.24061 (10)	0.0149 (3)
C32	0.57929 (19)	0.86504 (14)	0.20994 (10)	0.0139 (3)
C33	0.6219 (2)	0.78828 (14)	0.12072 (10)	0.0156 (3)
H33	0.5351	0.7228	0.0783	0.019*
C34	0.7873 (2)	0.80794 (15)	0.09528 (11)	0.0179 (3)
H34	0.8143	0.7561	0.0352	0.021*
C35	0.9184 (2)	0.90466 (15)	0.15754 (11)	0.0189 (3)
H35	1.0330	0.9174	0.1392	0.023*
C36	0.8808 (2)	0.98001 (15)	0.24417 (11)	0.0184 (3)
H36	0.9700	1.0445	0.2856	0.022*
C37	0.7105 (2)	0.96315 (14)	0.27295 (10)	0.0156 (3)
C38	0.6678 (2)	1.04133 (15)	0.36173 (11)	0.0206 (3)
H38	0.7560	1.1056	0.4044	0.025*
C39	0.5014 (2)	1.02521 (15)	0.38660 (11)	0.0215 (3)
H39	0.4740	1.0796	0.4457	0.026*
C310	0.3697 (2)	0.92871 (15)	0.32542 (11)	0.0189 (3)
H310	0.2540	0.9180	0.3431	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.01312 (19)	0.0168 (2)	0.01596 (19)	0.00086 (14)	0.00321 (14)	0.00375 (14)
O1	0.0159 (5)	0.0146 (5)	0.0213 (5)	0.0027 (4)	0.0068 (4)	0.0046 (4)
O2	0.0144 (5)	0.0215 (6)	0.0155 (5)	0.0019 (4)	0.0048 (4)	0.0045 (4)
O3	0.0130 (5)	0.0173 (5)	0.0175 (5)	0.0005 (4)	0.0011 (4)	0.0050 (4)
C11	0.0167 (7)	0.0150 (7)	0.0142 (6)	0.0018 (6)	0.0016 (5)	0.0031 (5)
C12	0.0138 (7)	0.0189 (7)	0.0118 (6)	0.0023 (6)	0.0001 (5)	0.0037 (5)
C13	0.0146 (7)	0.0199 (7)	0.0150 (7)	0.0012 (6)	0.0008 (5)	0.0025 (6)
C14	0.0138 (7)	0.0277 (9)	0.0186 (7)	0.0005 (6)	0.0021 (6)	0.0044 (6)
C15	0.0174 (8)	0.0276 (9)	0.0213 (8)	0.0084 (6)	0.0026 (6)	0.0022 (6)
C16	0.0201 (8)	0.0205 (8)	0.0204 (7)	0.0078 (6)	0.0008 (6)	0.0044 (6)
C17	0.0176 (7)	0.0194 (8)	0.0130 (6)	0.0039 (6)	−0.0006 (5)	0.0039 (5)
C18	0.0242 (8)	0.0168 (7)	0.0210 (7)	0.0027 (6)	0.0020 (6)	0.0079 (6)
C19	0.0233 (8)	0.0210 (8)	0.0229 (8)	−0.0002 (6)	0.0071 (6)	0.0092 (6)
C110	0.0192 (8)	0.0210 (8)	0.0203 (7)	0.0037 (6)	0.0076 (6)	0.0066 (6)
C21	0.0154 (7)	0.0132 (7)	0.0162 (7)	0.0006 (5)	0.0056 (5)	0.0034 (5)
C22	0.0156 (7)	0.0110 (7)	0.0161 (7)	0.0001 (5)	0.0017 (5)	0.0025 (5)
C23	0.0153 (7)	0.0155 (7)	0.0215 (7)	0.0011 (6)	0.0019 (6)	0.0025 (6)
C24	0.0207 (8)	0.0203 (8)	0.0242 (8)	0.0002 (6)	−0.0069 (6)	0.0057 (6)
C25	0.0314 (9)	0.0200 (8)	0.0159 (7)	−0.0027 (7)	−0.0018 (6)	0.0053 (6)
C26	0.0274 (8)	0.0165 (7)	0.0167 (7)	−0.0015 (6)	0.0058 (6)	0.0029 (6)
C27	0.0182 (7)	0.0126 (7)	0.0164 (7)	0.0001 (6)	0.0040 (6)	0.0027 (5)
C28	0.0186 (8)	0.0197 (8)	0.0232 (8)	0.0030 (6)	0.0090 (6)	0.0060 (6)
C29	0.0162 (7)	0.0237 (8)	0.0272 (8)	0.0067 (6)	0.0040 (6)	0.0107 (7)
C210	0.0189 (8)	0.0204 (8)	0.0175 (7)	0.0032 (6)	0.0024 (6)	0.0086 (6)
C31	0.0143 (7)	0.0132 (7)	0.0177 (7)	0.0015 (5)	0.0006 (5)	0.0061 (5)
C32	0.0133 (7)	0.0127 (7)	0.0168 (7)	0.0028 (5)	0.0013 (5)	0.0063 (5)
C33	0.0157 (7)	0.0157 (7)	0.0152 (7)	0.0025 (6)	0.0005 (5)	0.0052 (5)
C34	0.0192 (7)	0.0194 (8)	0.0171 (7)	0.0068 (6)	0.0053 (6)	0.0068 (6)
C35	0.0140 (7)	0.0208 (8)	0.0256 (8)	0.0038 (6)	0.0050 (6)	0.0115 (6)
C36	0.0148 (7)	0.0173 (7)	0.0231 (7)	−0.0006 (6)	−0.0002 (6)	0.0078 (6)
C37	0.0166 (7)	0.0129 (7)	0.0182 (7)	0.0023 (6)	0.0018 (6)	0.0063 (6)
C38	0.0253 (8)	0.0133 (7)	0.0202 (7)	−0.0006 (6)	0.0026 (6)	0.0012 (6)
C39	0.0290 (9)	0.0152 (7)	0.0197 (7)	0.0039 (6)	0.0080 (6)	0.0021 (6)
C310	0.0193 (8)	0.0175 (7)	0.0219 (7)	0.0044 (6)	0.0078 (6)	0.0065 (6)

Geometric parameters (Å, º)

P—O1	1.6425 (11)	C24—C25	1.407 (2)
P—O2	1.6376 (11)	C24—H24	0.950
P—O3	1.6086 (11)	C25—C26	1.366 (2)
O1—C11	1.3906 (18)	C25—H25	0.950
O2—C21	1.3889 (17)	C26—C27	1.415 (2)
O3—C31	1.4026 (17)	C26—H26	0.950
C11—C110	1.371 (2)	C27—C28	1.418 (2)
C11—C12	1.422 (2)	C28—C29	1.366 (2)
C12—C17	1.421 (2)	C28—H28	0.950
C12—C13	1.422 (2)	C29—C210	1.412 (2)
C13—C14	1.372 (2)	C29—H29	0.950
C13—H13	0.950	C210—H210	0.950
C14—C15	1.405 (2)	C31—C310	1.365 (2)
C14—H14	0.950	C31—C32	1.420 (2)
C15—C16	1.369 (2)	C32—C33	1.417 (2)
C15—H15	0.950	C32—C37	1.425 (2)
C16—C17	1.419 (2)	C33—C34	1.367 (2)
C16—H16	0.950	C33—H33	0.950
C17—C18	1.418 (2)	C34—C35	1.413 (2)
C18—C19	1.362 (2)	C34—H34	0.950
C18—H18	0.950	C35—C36	1.368 (2)
C19—C110	1.412 (2)	C35—H35	0.950
C19—H19	0.950	C36—C37	1.417 (2)
C110—H110	0.950	C36—H36	0.950
C21—C210	1.368 (2)	C37—C38	1.417 (2)
C21—C22	1.424 (2)	C38—C39	1.364 (2)
C22—C27	1.419 (2)	C38—H38	0.950
C22—C23	1.419 (2)	C39—C310	1.409 (2)
C23—C24	1.369 (2)	C39—H39	0.950
C23—H23	0.950	C310—H310	0.950
O2—P—O1	94.73 (5)	C26—C25—C24	120.00 (14)
O3—P—O1	98.02 (5)	C26—C25—H25	120.0
O3—P—O2	101.91 (6)	C24—C25—H25	120.0
C11—O1—P	119.03 (9)	C25—C26—C27	121.32 (15)
C21—O2—P	124.86 (9)	C25—C26—H26	119.3
C31—O3—P	127.49 (9)	C27—C26—H26	119.3
C110—C11—O1	123.07 (13)	C26—C27—C28	121.88 (14)
C110—C11—C12	121.17 (14)	C26—C27—C22	118.32 (14)
O1—C11—C12	115.75 (13)	C28—C27—C22	119.80 (13)
C17—C12—C11	118.04 (13)	C29—C28—C27	120.50 (14)
C17—C12—C13	119.60 (14)	C29—C28—H28	119.8
C11—C12—C13	122.36 (14)	C27—C28—H28	119.8
C14—C13—C12	119.83 (15)	C28—C29—C210	120.64 (14)
C14—C13—H13	120.1	C28—C29—H29	119.7
C12—C13—H13	120.1	C210—C29—H29	119.7
C13—C14—C15	120.61 (15)	C21—C210—C29	119.57 (14)
C13—C14—H14	119.7	C21—C210—H210	120.2
C15—C14—H14	119.7	C29—C210—H210	120.2
C16—C15—C14	120.85 (15)	C310—C31—O3	119.90 (13)
C16—C15—H15	119.6	C310—C31—C32	122.43 (14)
C14—C15—H15	119.6	O3—C31—C32	117.50 (12)
C15—C16—C17	120.39 (15)	C33—C32—C31	123.44 (13)
C15—C16—H16	119.8	C33—C32—C37	119.35 (13)
C17—C16—H16	119.8	C31—C32—C37	117.21 (13)
C18—C17—C16	121.40 (14)	C34—C33—C32	120.40 (14)
C18—C17—C12	119.88 (14)	C34—C33—H33	119.8
C16—C17—C12	118.72 (14)	C32—C33—H33	119.8
C19—C18—C17	120.05 (14)	C33—C34—C35	120.60 (14)
C19—C18—H18	120.0	C33—C34—H34	119.7
C17—C18—H18	120.0	C35—C34—H34	119.7
C18—C19—C110	121.03 (15)	C36—C35—C34	120.18 (14)
C18—C19—H19	119.5	C36—C35—H35	119.9
C110—C19—H19	119.5	C34—C35—H35	119.9
C11—C110—C19	119.83 (14)	C35—C36—C37	120.94 (14)
C11—C110—H110	120.1	C35—C36—H36	119.5
C19—C110—H110	120.1	C37—C36—H36	119.5
C210—C21—O2	123.56 (13)	C36—C37—C38	121.89 (14)
C210—C21—C22	121.87 (13)	C36—C37—C32	118.53 (13)
O2—C21—C22	114.56 (13)	C38—C37—C32	119.58 (14)
C27—C22—C23	119.57 (13)	C39—C38—C37	120.70 (14)
C27—C22—C21	117.62 (13)	C39—C38—H38	119.6
C23—C22—C21	122.81 (13)	C37—C38—H38	119.6
C24—C23—C22	120.00 (14)	C38—C39—C310	120.62 (14)
C24—C23—H23	120.0	C38—C39—H39	119.7
C22—C23—H23	120.0	C310—C39—H39	119.7
C23—C24—C25	120.78 (15)	C31—C310—C39	119.43 (14)
C23—C24—H24	119.6	C31—C310—H310	120.3
C25—C24—H24	119.6	C39—C310—H310	120.3
O3—P—O1—C11	−171.12 (10)	C23—C24—C25—C26	−0.2 (2)
O2—P—O1—C11	86.13 (10)	C24—C25—C26—C27	−0.5 (2)
O3—P—O2—C21	107.89 (11)	C25—C26—C27—C28	−179.49 (15)
O1—P—O2—C21	−152.88 (11)	C25—C26—C27—C22	0.7 (2)
O2—P—O3—C31	30.61 (12)	C23—C22—C27—C26	−0.3 (2)
O1—P—O3—C31	−65.99 (12)	C21—C22—C27—C26	179.94 (13)
P—O1—C11—C110	−19.62 (18)	C23—C22—C27—C28	179.89 (13)
P—O1—C11—C12	160.36 (10)	C21—C22—C27—C28	0.1 (2)
C110—C11—C12—C17	0.2 (2)	C26—C27—C28—C29	−179.54 (15)
O1—C11—C12—C17	−179.74 (12)	C22—C27—C28—C29	0.3 (2)
C110—C11—C12—C13	−179.48 (14)	C27—C28—C29—C210	−0.8 (2)
O1—C11—C12—C13	0.5 (2)	O2—C21—C210—C29	−179.16 (14)
C17—C12—C13—C14	0.2 (2)	C22—C21—C210—C29	−0.6 (2)
C11—C12—C13—C14	179.88 (14)	C28—C29—C210—C21	1.0 (2)
C12—C13—C14—C15	−0.1 (2)	P—O3—C31—C310	−75.04 (17)
C13—C14—C15—C16	0.2 (2)	P—O3—C31—C32	109.66 (13)
C14—C15—C16—C17	−0.3 (2)	C310—C31—C32—C33	−177.79 (14)
C15—C16—C17—C18	179.83 (14)	O3—C31—C32—C33	−2.6 (2)
C15—C16—C17—C12	0.4 (2)	C310—C31—C32—C37	1.6 (2)
C11—C12—C17—C18	0.5 (2)	O3—C31—C32—C37	176.76 (12)
C13—C12—C17—C18	−179.77 (13)	C31—C32—C33—C34	179.40 (14)
C11—C12—C17—C16	179.98 (13)	C37—C32—C33—C34	0.1 (2)
C13—C12—C17—C16	−0.3 (2)	C32—C33—C34—C35	0.2 (2)
C16—C17—C18—C19	179.97 (14)	C33—C34—C35—C36	−0.1 (2)
C12—C17—C18—C19	−0.6 (2)	C34—C35—C36—C37	−0.2 (2)
C17—C18—C19—C110	−0.1 (2)	C35—C36—C37—C38	−179.09 (14)
O1—C11—C110—C19	179.07 (13)	C35—C36—C37—C32	0.5 (2)
C12—C11—C110—C19	−0.9 (2)	C33—C32—C37—C36	−0.4 (2)
C18—C19—C110—C11	0.8 (2)	C31—C32—C37—C36	−179.79 (13)
P—O2—C21—C210	−19.9 (2)	C33—C32—C37—C38	179.20 (13)
P—O2—C21—C22	161.44 (10)	C31—C32—C37—C38	−0.2 (2)
C210—C21—C22—C27	0.0 (2)	C36—C37—C38—C39	178.37 (15)
O2—C21—C22—C27	178.73 (12)	C32—C37—C38—C39	−1.2 (2)
C210—C21—C22—C23	−179.70 (14)	C37—C38—C39—C310	1.3 (2)
O2—C21—C22—C23	−1.0 (2)	O3—C31—C310—C39	−176.61 (13)
C27—C22—C23—C24	−0.4 (2)	C32—C31—C310—C39	−1.5 (2)
C21—C22—C23—C24	179.40 (14)	C38—C39—C310—C31	0.1 (2)
C22—C23—C24—C25	0.6 (2)