(R)-3,3′-Diphenyl-5,6,7,8,5′,6′,7′,8′-octa­hydro-1,1′-binaphthyl-2,2′-diyl chloro­phosphate

Li, Y.-P.; Ng, S.W.

doi:10.1107/S1600536807031479

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(R)-3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-1,1'-binaphthyl-2,2'-diyl chlorophosphate

Y.-P. Li and S. W. Ng

The two fused ring systems in the 1,1'-bi-2-naphthol derivative title compound, C₃₂H₂₈ClO₃P, are twisted by 61.1 (1)° about the linking C-C bond, thus conferring chirality on the molecule. In one of the fused ring systems, the four-atom aliphatic chain is disordered over two sites in a 0.5:0.5 ratio.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031479/hb2462sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031479/hb2462Isup2.hkl Contains datablock I

CCDC reference: 657653

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.036
wR factor = 0.099
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for        C18

Author Response: The four-carbon chain is disordered over two sites.


Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit    P 2ac ab
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.17 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C18'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C24    -   C25    ...       1.38 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H16B   ..  H17B    ..       1.97 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.49
           From the CIF: _reflns_number_total               6089
           Count of symmetry unique reflns         3414
           Completeness (_total/calc)            178.35%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2675
           Fraction of Friedel pairs measured     0.784
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P1     = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         52

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

Comment top

3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-phosphate is a highly enantioselective catalyst (Chen et al., 2006) as is starting reactant 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diol (McDougal & Schaus, 2003). The reaction of the diol with phosphorus oxychloride has yielded the title chlorophosphate, (I), (Fig. 1) which is also expected to exhibit such activity.

Related literature top

For a report on the enantioselective catalytic property of the related 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-phosphate, see Chen et al. (2006). For a report on the synthesis of the 3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1']-binaphthalenyl-2,2'-diol reactant, see McDougal & Schaus (2003).

Experimental top

To a solution of (R)-3,3'-diphenyl-5,6,7,8,5',6',7',8'-octahydro-[1,1'] binaphthalenyl-2,2'-diol (2 mmol) in pyridine (5 ml) was added phosphorus oxychloride (4.0 mmol) at room temperature under nitrogen. The mixture was stirred at 343 K for 3 h. The solvent was then removed and the product purified by column chromatography on silica gel. Colorless blocks of (I) were obtained by recrystallization from ethanol.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006 or??2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level (H atoms as spheres of arbitrary radius). The disorder is not shown.

(R)-3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octahydro-1,1'-binaphthyl- 2,2'-diyl chlorophosphate top

Crystal data top

C₃₂H₂₈ClO₃P	F(000) = 1104
M_r = 526.96	D_x = 1.320 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac ab	Cell parameters from 7841 reflections
a = 12.6642 (8) Å	θ = 2.2–23.6°
b = 13.1613 (8) Å	µ = 0.24 mm⁻¹
c = 15.9097 (9) Å	T = 295 K
V = 2651.8 (3) Å³	Block, colorless
Z = 4	0.32 × 0.17 × 0.07 mm

Data collection top

Bruker APEX CCD diffractometer	4949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
φ and ω scans	h = −16→16
33491 measured reflections	k = −17→16
6089 independent reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0547P)² + 0.1321P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6089 reflections	Δρ_max = 0.16 e Å⁻³
370 parameters	Δρ_min = −0.23 e Å⁻³
52 restraints	Absolute structure: Flack (1983), 2674 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

Crystal data top

C₃₂H₂₈ClO₃P	V = 2651.8 (3) Å³
M_r = 526.96	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 12.6642 (8) Å	µ = 0.24 mm⁻¹
b = 13.1613 (8) Å	T = 295 K
c = 15.9097 (9) Å	0.32 × 0.17 × 0.07 mm

Data collection top

Bruker APEX CCD diffractometer	4949 reflections with I > 2σ(I)
33491 measured reflections	R_int = 0.032
6089 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.16 e Å⁻³
S = 1.03	Δρ_min = −0.23 e Å⁻³
6089 reflections	Absolute structure: Flack (1983), 2674 Friedel pairs
370 parameters	Absolute structure parameter: 0.02 (6)
52 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.69670 (4)	0.39625 (5)	0.93762 (4)	0.06273 (16)
P1	0.82905 (4)	0.40064 (4)	0.87055 (3)	0.04711 (13)
O1	0.88918 (10)	0.30781 (10)	0.91181 (8)	0.0459 (3)
O2	0.89086 (10)	0.49825 (10)	0.89966 (8)	0.0464 (3)
O3	0.81117 (12)	0.39828 (14)	0.78038 (9)	0.0666 (4)
C1	0.99403 (18)	0.15174 (17)	0.81908 (14)	0.0541 (5)
C2	1.0106 (2)	0.0517 (2)	0.84163 (17)	0.0743 (7)
H2	1.0603	0.0361	0.8827	0.089*
C3	0.9543 (3)	−0.0251 (2)	0.8038 (2)	0.0937 (9)
H3	0.9651	−0.0921	0.8205	0.112*
C4	0.8838 (3)	−0.0043 (3)	0.7430 (2)	0.0931 (10)
H4	0.8458	−0.0568	0.7181	0.112*
C5	0.8675 (3)	0.0940 (3)	0.71751 (18)	0.0898 (9)
H5	0.8198	0.1078	0.6746	0.108*
C6	0.9218 (2)	0.1723 (2)	0.75553 (16)	0.0727 (7)
H6	0.9100	0.2390	0.7386	0.087*
C7	1.05299 (14)	0.37665 (14)	0.96221 (11)	0.0398 (4)
C8	1.00118 (14)	0.30754 (15)	0.91088 (11)	0.0420 (4)
C9	1.05190 (15)	0.23363 (15)	0.86370 (12)	0.0456 (4)
C10	1.16196 (16)	0.23720 (16)	0.86518 (13)	0.0497 (5)
H10	1.1995	0.1878	0.8360	0.060*
C11	1.21748 (15)	0.31100 (17)	0.90821 (12)	0.0477 (5)
C12	1.16399 (14)	0.38174 (15)	0.95733 (11)	0.0445 (4)
C13	1.33695 (16)	0.3147 (2)	0.89788 (15)	0.0648 (6)
H13A	1.3655	0.2481	0.9108	0.078*
H13B	1.3531	0.3292	0.8395	0.078*
C14	1.39153 (16)	0.3922 (2)	0.95210 (17)	0.0703 (7)
H14A	1.4026	0.3639	1.0077	0.084*
H14B	1.4602	0.4075	0.9282	0.084*
C15	1.32899 (18)	0.4890 (2)	0.95974 (18)	0.0704 (7)
H15A	1.3185	0.5185	0.9045	0.085*
H15B	1.3677	0.5376	0.9937	0.085*
C16	1.22350 (17)	0.46740 (19)	0.99976 (16)	0.0612 (6)
H16A	1.1807	0.5285	0.9978	0.073*
H16B	1.2344	0.4501	1.0584	0.073*
C17	1.0695 (7)	0.3533 (7)	1.1426 (6)	0.050 (2)	0.50
H17A	1.0431	0.2891	1.1214	0.059*	0.50
H17B	1.1425	0.3604	1.1251	0.059*	0.50
C18	1.0632 (9)	0.3543 (9)	1.2377 (6)	0.126 (5)	0.50
H18A	1.1287	0.3832	1.2583	0.152*	0.50
H18B	1.0614	0.2841	1.2562	0.152*	0.50
C19	0.9729 (7)	0.4097 (7)	1.2819 (5)	0.092 (2)	0.50
H19A	0.9066	0.3754	1.2707	0.111*	0.50
H19B	0.9846	0.4098	1.3422	0.111*	0.50
C20	0.9683 (8)	0.5169 (7)	1.2499 (5)	0.068 (3)	0.50
H20A	1.0353	0.5512	1.2585	0.081*	0.50
H20B	0.9132	0.5550	1.2782	0.081*	0.50
C17'	1.0817 (8)	0.3751 (8)	1.1556 (6)	0.067 (3)	0.50
H17C	1.1062	0.3204	1.1197	0.081*	0.50
H17D	1.1425	0.4161	1.1706	0.081*	0.50
C18'	1.0346 (6)	0.3299 (5)	1.2351 (4)	0.0596 (18)	0.50
H18C	0.9663	0.2989	1.2249	0.072*	0.50
H18D	1.0814	0.2808	1.2611	0.072*	0.50
C19'	1.0257 (6)	0.4258 (5)	1.2857 (4)	0.078 (2)	0.50
H19C	1.0103	0.4092	1.3438	0.094*	0.50
H19D	1.0922	0.4623	1.2840	0.094*	0.50
C20'	0.9400 (7)	0.4909 (8)	1.2510 (5)	0.068 (3)	0.50
H20C	0.9433	0.5568	1.2781	0.081*	0.50
H20D	0.8725	0.4606	1.2653	0.081*	0.50
C21	0.99091 (14)	0.44335 (15)	1.01926 (12)	0.0407 (4)
C22	0.91440 (14)	0.50784 (14)	0.98597 (12)	0.0424 (4)
C23	0.85660 (15)	0.57704 (15)	1.03315 (14)	0.0490 (5)
C24	0.87462 (17)	0.57417 (18)	1.11978 (15)	0.0592 (6)
H24	0.8384	0.6195	1.1541	0.071*
C25	0.94419 (17)	0.50649 (18)	1.15635 (12)	0.0585 (6)
C26	1.00400 (15)	0.44054 (16)	1.10670 (12)	0.0484 (5)
C27	0.77742 (17)	0.64701 (16)	0.99610 (17)	0.0581 (6)
C28	0.6822 (2)	0.6646 (2)	1.0379 (2)	0.0778 (8)
H28	0.6687	0.6319	1.0886	0.093*
C29	0.6082 (2)	0.7297 (3)	1.0048 (3)	0.1066 (12)
H29	0.5449	0.7405	1.0331	0.128*
C30	0.6273 (3)	0.7787 (3)	0.9303 (3)	0.1088 (13)
H30	0.5763	0.8215	0.9076	0.131*
C31	0.7210 (3)	0.7649 (2)	0.8894 (2)	0.0928 (10)
H31	0.7350	0.8002	0.8399	0.111*
C32	0.7958 (2)	0.69762 (18)	0.92191 (18)	0.0714 (7)
H32	0.8587	0.6869	0.8931	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0366 (2)	0.0759 (4)	0.0756 (3)	0.0012 (3)	0.0016 (2)	0.0015 (3)
P1	0.0374 (2)	0.0571 (3)	0.0468 (3)	0.0049 (2)	−0.0062 (2)	−0.0003 (2)
O1	0.0359 (6)	0.0487 (8)	0.0532 (8)	0.0021 (6)	−0.0048 (6)	−0.0029 (6)
O2	0.0410 (7)	0.0504 (8)	0.0476 (7)	0.0046 (6)	−0.0005 (5)	0.0040 (6)
O3	0.0625 (9)	0.0863 (11)	0.0510 (8)	0.0101 (9)	−0.0140 (7)	−0.0041 (8)
C1	0.0601 (12)	0.0541 (13)	0.0482 (12)	0.0031 (10)	0.0055 (10)	−0.0119 (10)
C2	0.0904 (19)	0.0542 (15)	0.0783 (18)	0.0092 (13)	−0.0051 (14)	−0.0167 (13)
C3	0.128 (3)	0.0570 (16)	0.096 (2)	0.0008 (18)	0.003 (2)	−0.0223 (15)
C4	0.108 (2)	0.082 (2)	0.089 (2)	−0.0242 (18)	0.0082 (19)	−0.0389 (17)
C5	0.099 (2)	0.097 (2)	0.0735 (17)	−0.0095 (19)	−0.0192 (15)	−0.0266 (17)
C6	0.0865 (18)	0.0690 (16)	0.0626 (15)	−0.0006 (14)	−0.0148 (13)	−0.0146 (12)
C7	0.0365 (8)	0.0427 (10)	0.0403 (9)	0.0039 (7)	−0.0010 (7)	0.0008 (7)
C8	0.0359 (9)	0.0480 (11)	0.0421 (10)	0.0041 (8)	−0.0029 (7)	−0.0002 (8)
C9	0.0485 (10)	0.0461 (11)	0.0423 (10)	0.0068 (8)	−0.0019 (9)	−0.0021 (8)
C10	0.0509 (11)	0.0513 (11)	0.0470 (11)	0.0162 (9)	0.0059 (9)	−0.0005 (9)
C11	0.0387 (9)	0.0582 (12)	0.0463 (10)	0.0090 (9)	0.0007 (8)	0.0103 (9)
C12	0.0354 (8)	0.0522 (11)	0.0458 (10)	0.0026 (8)	−0.0010 (7)	0.0024 (8)
C13	0.0395 (10)	0.0830 (17)	0.0720 (15)	0.0167 (11)	0.0080 (10)	0.0097 (13)
C14	0.0356 (10)	0.0850 (17)	0.0901 (17)	0.0012 (12)	−0.0020 (10)	0.0225 (15)
C15	0.0482 (12)	0.0728 (16)	0.0902 (18)	−0.0076 (11)	−0.0053 (12)	0.0125 (13)
C16	0.0432 (11)	0.0640 (14)	0.0763 (14)	−0.0081 (10)	−0.0002 (10)	−0.0099 (12)
C17	0.041 (3)	0.065 (4)	0.043 (4)	0.001 (3)	−0.008 (2)	−0.003 (3)
C18	0.166 (9)	0.137 (8)	0.076 (5)	0.039 (7)	−0.013 (6)	−0.010 (5)
C19	0.108 (5)	0.121 (6)	0.048 (3)	−0.048 (5)	−0.002 (4)	0.003 (3)
C20	0.069 (5)	0.089 (6)	0.045 (3)	−0.006 (4)	0.006 (3)	−0.016 (3)
C17'	0.072 (5)	0.085 (6)	0.045 (4)	0.011 (4)	−0.012 (3)	−0.001 (4)
C18'	0.075 (3)	0.058 (3)	0.046 (3)	−0.021 (3)	−0.015 (3)	0.014 (2)
C19'	0.081 (4)	0.099 (5)	0.053 (3)	−0.017 (4)	−0.010 (3)	−0.012 (3)
C20'	0.071 (5)	0.084 (6)	0.048 (4)	−0.010 (4)	0.005 (3)	−0.016 (3)
C21	0.0337 (8)	0.0426 (10)	0.0459 (10)	−0.0023 (8)	0.0018 (7)	−0.0036 (8)
C22	0.0345 (8)	0.0467 (11)	0.0459 (10)	−0.0032 (8)	0.0018 (7)	−0.0008 (8)
C23	0.0385 (9)	0.0420 (11)	0.0664 (13)	0.0006 (8)	0.0041 (9)	−0.0078 (9)
C24	0.0507 (11)	0.0632 (14)	0.0636 (13)	0.0060 (10)	0.0095 (10)	−0.0188 (11)
C25	0.0500 (11)	0.0778 (16)	0.0477 (12)	0.0016 (11)	0.0022 (9)	−0.0139 (11)
C26	0.0415 (10)	0.0582 (13)	0.0456 (11)	0.0005 (9)	0.0002 (8)	−0.0038 (9)
C27	0.0485 (11)	0.0443 (11)	0.0814 (16)	0.0058 (9)	−0.0034 (11)	−0.0111 (11)
C28	0.0533 (13)	0.0681 (16)	0.112 (2)	0.0156 (12)	0.0060 (14)	−0.0163 (14)
C29	0.0623 (17)	0.091 (2)	0.166 (4)	0.0345 (17)	−0.009 (2)	−0.033 (2)
C30	0.083 (2)	0.069 (2)	0.175 (4)	0.0355 (17)	−0.043 (2)	−0.025 (2)
C31	0.101 (2)	0.0539 (16)	0.123 (3)	0.0139 (15)	−0.030 (2)	0.0059 (16)
C32	0.0642 (14)	0.0524 (14)	0.0977 (19)	0.0071 (12)	−0.0093 (13)	0.0046 (13)

Geometric parameters (Å, º) top

Cl1—P1	1.9878 (7)	C17—H17B	0.9700
P1—O3	1.4526 (15)	C18—C19	1.528 (8)
P1—O2	1.5741 (14)	C18—H18A	0.9700
P1—O1	1.5822 (14)	C18—H18B	0.9700
O1—C8	1.418 (2)	C19—C20	1.501 (8)
O2—C22	1.411 (2)	C19—H19A	0.9700
C1—C2	1.381 (3)	C19—H19B	0.9700
C1—C6	1.390 (3)	C20—C25	1.525 (7)
C1—C9	1.484 (3)	C20—H20A	0.9700
C2—C3	1.376 (4)	C20—H20B	0.9700
C2—H2	0.9300	C17'—C18'	1.520 (8)
C3—C4	1.346 (5)	C17'—C26	1.522 (8)
C3—H3	0.9300	C17'—H17C	0.9700
C4—C5	1.371 (5)	C17'—H17D	0.9700
C4—H4	0.9300	C18'—C19'	1.502 (7)
C5—C6	1.379 (4)	C18'—H18C	0.9700
C5—H5	0.9300	C18'—H18D	0.9700
C6—H6	0.9300	C19'—C20'	1.489 (8)
C7—C8	1.387 (3)	C19'—H19C	0.9700
C7—C12	1.410 (2)	C19'—H19D	0.9700
C7—C21	1.487 (2)	C20'—C25	1.521 (7)
C8—C9	1.386 (3)	C20'—H20C	0.9700
C9—C10	1.395 (3)	C20'—H20D	0.9700
C10—C11	1.381 (3)	C21—C22	1.393 (3)
C10—H10	0.9300	C21—C26	1.401 (3)
C11—C12	1.391 (3)	C22—C23	1.389 (3)
C11—C13	1.523 (3)	C23—C24	1.398 (3)
C12—C16	1.515 (3)	C23—C27	1.484 (3)
C13—C14	1.505 (4)	C24—C25	1.381 (3)
C13—H13A	0.9700	C24—H24	0.9300
C13—H13B	0.9700	C25—C26	1.397 (3)
C14—C15	1.505 (3)	C27—C32	1.375 (4)
C14—H14A	0.9700	C27—C28	1.396 (3)
C14—H14B	0.9700	C28—C29	1.375 (4)
C15—C16	1.507 (3)	C28—H28	0.9300
C15—H15A	0.9700	C29—C30	1.371 (5)
C15—H15B	0.9700	C29—H29	0.9300
C16—H16A	0.9700	C30—C31	1.367 (5)
C16—H16B	0.9700	C30—H30	0.9300
C17—C18	1.514 (8)	C31—C32	1.396 (4)
C17—C26	1.528 (7)	C31—H31	0.9300
C17—H17A	0.9700	C32—H32	0.9300

O3—P1—O2	112.68 (9)	C19—C18—H18B	107.3
O3—P1—O1	117.92 (9)	H18A—C18—H18B	106.9
O2—P1—O1	105.59 (7)	C20—C19—C18	108.7 (8)
O3—P1—Cl1	113.46 (7)	C20—C19—H19A	110.0
O2—P1—Cl1	106.56 (6)	C18—C19—H19A	110.0
O1—P1—Cl1	99.24 (6)	C20—C19—H19B	110.0
C8—O1—P1	118.61 (13)	C18—C19—H19B	110.0
C22—O2—P1	117.68 (12)	H19A—C19—H19B	108.3
C2—C1—C6	118.3 (2)	C19—C20—C25	104.8 (6)
C2—C1—C9	119.5 (2)	C19—C20—H20A	110.8
C6—C1—C9	122.1 (2)	C25—C20—H20A	110.8
C3—C2—C1	120.5 (3)	C19—C20—H20B	110.8
C3—C2—H2	119.7	C25—C20—H20B	110.8
C1—C2—H2	119.7	H20A—C20—H20B	108.9
C4—C3—C2	120.6 (3)	C18'—C17'—C26	113.1 (7)
C4—C3—H3	119.7	C18'—C17'—H17C	109.0
C2—C3—H3	119.7	C26—C17'—H17C	109.0
C3—C4—C5	120.3 (3)	C18'—C17'—H17D	109.0
C3—C4—H4	119.8	C26—C17'—H17D	109.0
C5—C4—H4	119.8	H17C—C17'—H17D	107.8
C4—C5—C6	120.1 (3)	C19'—C18'—C17'	98.4 (7)
C4—C5—H5	120.0	C19'—C18'—H18C	112.1
C6—C5—H5	120.0	C17'—C18'—H18C	112.1
C5—C6—C1	120.1 (3)	C19'—C18'—H18D	112.1
C5—C6—H6	120.0	C17'—C18'—H18D	112.1
C1—C6—H6	120.0	H18C—C18'—H18D	109.7
C8—C7—C12	118.06 (17)	C20'—C19'—C18'	109.8 (7)
C8—C7—C21	119.75 (15)	C20'—C19'—H19C	109.7
C12—C7—C21	122.19 (16)	C18'—C19'—H19C	109.7
C9—C8—C7	124.03 (16)	C20'—C19'—H19D	109.7
C9—C8—O1	118.08 (17)	C18'—C19'—H19D	109.7
C7—C8—O1	117.72 (16)	H19C—C19'—H19D	108.2
C8—C9—C10	115.48 (18)	C19'—C20'—C25	114.8 (7)
C8—C9—C1	122.66 (17)	C19'—C20'—H20C	108.6
C10—C9—C1	121.74 (18)	C25—C20'—H20C	108.6
C11—C10—C9	122.75 (18)	C19'—C20'—H20D	108.6
C11—C10—H10	118.6	C25—C20'—H20D	108.6
C9—C10—H10	118.6	H20C—C20'—H20D	107.5
C10—C11—C12	120.08 (17)	C22—C21—C26	118.42 (17)
C10—C11—C13	118.4 (2)	C22—C21—C7	119.69 (16)
C12—C11—C13	121.5 (2)	C26—C21—C7	121.84 (17)
C11—C12—C7	118.99 (18)	C23—C22—C21	124.11 (18)
C11—C12—C16	120.40 (17)	C23—C22—O2	118.26 (17)
C7—C12—C16	120.46 (17)	C21—C22—O2	117.55 (16)
C14—C13—C11	114.6 (2)	C22—C23—C24	115.42 (19)
C14—C13—H13A	108.6	C22—C23—C27	123.27 (19)
C11—C13—H13A	108.6	C24—C23—C27	121.26 (19)
C14—C13—H13B	108.6	C25—C24—C23	122.48 (19)
C11—C13—H13B	108.6	C25—C24—H24	118.8
H13A—C13—H13B	107.6	C23—C24—H24	118.8
C15—C14—C13	112.25 (19)	C24—C25—C26	120.55 (19)
C15—C14—H14A	109.2	C24—C25—C20'	118.8 (4)
C13—C14—H14A	109.2	C26—C25—C20'	119.7 (4)
C15—C14—H14B	109.2	C24—C25—C20	118.7 (4)
C13—C14—H14B	109.2	C26—C25—C20	119.9 (5)
H14A—C14—H14B	107.9	C25—C26—C21	118.74 (18)
C14—C15—C16	109.9 (2)	C25—C26—C17'	114.4 (4)
C14—C15—H15A	109.7	C21—C26—C17'	126.8 (4)
C16—C15—H15A	109.7	C25—C26—C17	123.4 (4)
C14—C15—H15B	109.7	C21—C26—C17	117.1 (4)
C16—C15—H15B	109.7	C32—C27—C28	118.3 (2)
H15A—C15—H15B	108.2	C32—C27—C23	121.8 (2)
C15—C16—C12	113.2 (2)	C28—C27—C23	119.8 (2)
C15—C16—H16A	108.9	C29—C28—C27	120.7 (3)
C12—C16—H16A	108.9	C29—C28—H28	119.7
C15—C16—H16B	108.9	C27—C28—H28	119.7
C12—C16—H16B	108.9	C28—C29—C30	120.3 (3)
H16A—C16—H16B	107.8	C28—C29—H29	119.9
C18—C17—C26	109.8 (7)	C30—C29—H29	119.9
C18—C17—H17A	109.7	C31—C30—C29	120.2 (3)
C26—C17—H17A	109.7	C31—C30—H30	119.9
C18—C17—H17B	109.7	C29—C30—H30	119.9
C26—C17—H17B	109.7	C30—C31—C32	119.8 (3)
H17A—C17—H17B	108.2	C30—C31—H31	120.1
C17—C18—C19	120.3 (9)	C32—C31—H31	120.1
C17—C18—H18A	107.3	C27—C32—C31	120.7 (3)
C19—C18—H18A	107.3	C27—C32—H32	119.6
C17—C18—H18B	107.3	C31—C32—H32	119.6

O3—P1—O1—C8	84.18 (16)	C12—C7—C21—C26	−61.5 (3)
O2—P1—O1—C8	−42.76 (15)	C26—C21—C22—C23	6.4 (3)
Cl1—P1—O1—C8	−152.95 (12)	C7—C21—C22—C23	−176.17 (17)
O3—P1—O2—C22	−178.91 (13)	C26—C21—C22—O2	−170.31 (17)
O1—P1—O2—C22	−48.85 (13)	C7—C21—C22—O2	7.1 (2)
Cl1—P1—O2—C22	56.04 (13)	P1—O2—C22—C23	−105.79 (17)
C6—C1—C2—C3	−2.1 (4)	P1—O2—C22—C21	71.10 (18)
C9—C1—C2—C3	177.0 (2)	C21—C22—C23—C24	−4.2 (3)
C1—C2—C3—C4	1.5 (5)	O2—C22—C23—C24	172.50 (17)
C2—C3—C4—C5	0.3 (5)	C21—C22—C23—C27	178.32 (19)
C3—C4—C5—C6	−1.5 (5)	O2—C22—C23—C27	−5.0 (3)
C4—C5—C6—C1	0.8 (5)	C22—C23—C24—C25	−0.7 (3)
C2—C1—C6—C5	1.0 (4)	C27—C23—C24—C25	176.9 (2)
C9—C1—C6—C5	−178.1 (2)	C23—C24—C25—C26	3.2 (3)
C12—C7—C8—C9	9.3 (3)	C23—C24—C25—C20'	−165.5 (5)
C21—C7—C8—C9	−171.49 (18)	C23—C24—C25—C20	173.0 (4)
C12—C7—C8—O1	−175.67 (17)	C19'—C20'—C25—C24	−173.4 (5)
C21—C7—C8—O1	3.6 (3)	C19'—C20'—C25—C26	17.8 (9)
P1—O1—C8—C9	−113.98 (17)	C19'—C20'—C25—C20	−78 (2)
P1—O1—C8—C7	70.7 (2)	C19—C20—C25—C24	140.2 (6)
C7—C8—C9—C10	−5.0 (3)	C19—C20—C25—C26	−49.9 (8)
O1—C8—C9—C10	179.97 (17)	C19—C20—C25—C20'	45 (2)
C7—C8—C9—C1	171.05 (19)	C24—C25—C26—C21	−0.9 (3)
O1—C8—C9—C1	−4.0 (3)	C20'—C25—C26—C21	167.7 (4)
C2—C1—C9—C8	−117.0 (3)	C20—C25—C26—C21	−170.7 (4)
C6—C1—C9—C8	62.0 (3)	C24—C25—C26—C17'	176.5 (5)
C2—C1—C9—C10	58.8 (3)	C20'—C25—C26—C17'	−14.9 (7)
C6—C1—C9—C10	−122.2 (3)	C20—C25—C26—C17'	6.7 (7)
C8—C9—C10—C11	−2.1 (3)	C24—C25—C26—C17	−170.4 (5)
C1—C9—C10—C11	−178.14 (18)	C20'—C25—C26—C17	−1.8 (7)
C9—C10—C11—C12	4.5 (3)	C20—C25—C26—C17	19.9 (7)
C9—C10—C11—C13	−173.4 (2)	C22—C21—C26—C25	−3.6 (3)
C10—C11—C12—C7	0.0 (3)	C7—C21—C26—C25	179.01 (18)
C13—C11—C12—C7	177.81 (19)	C22—C21—C26—C17'	179.4 (6)
C10—C11—C12—C16	−175.7 (2)	C7—C21—C26—C17'	2.0 (6)
C13—C11—C12—C16	2.2 (3)	C22—C21—C26—C17	166.5 (5)
C8—C7—C12—C11	−6.5 (3)	C7—C21—C26—C17	−10.9 (5)
C21—C7—C12—C11	174.34 (17)	C18'—C17'—C26—C25	44.0 (9)
C8—C7—C12—C16	169.16 (19)	C18'—C17'—C26—C21	−138.8 (5)
C21—C7—C12—C16	−10.0 (3)	C18'—C17'—C26—C17	−87 (3)
C10—C11—C13—C14	−175.55 (19)	C18—C17—C26—C25	−2.9 (10)
C12—C11—C13—C14	6.6 (3)	C18—C17—C26—C21	−172.5 (6)
C11—C13—C14—C15	−38.1 (3)	C18—C17—C26—C17'	53 (3)
C13—C14—C15—C16	61.0 (3)	C22—C23—C27—C32	−42.4 (3)
C14—C15—C16—C12	−51.5 (3)	C24—C23—C27—C32	140.2 (2)
C11—C12—C16—C15	20.8 (3)	C22—C23—C27—C28	139.1 (2)
C7—C12—C16—C15	−154.8 (2)	C24—C23—C27—C28	−38.3 (3)
C26—C17—C18—C19	20.1 (14)	C32—C27—C28—C29	1.0 (4)
C17—C18—C19—C20	−53.2 (13)	C23—C27—C28—C29	179.6 (3)
C18—C19—C20—C25	62.4 (9)	C27—C28—C29—C30	−0.3 (5)
C26—C17'—C18'—C19'	−70.3 (8)	C28—C29—C30—C31	−1.4 (5)
C17'—C18'—C19'—C20'	71.4 (8)	C29—C30—C31—C32	2.4 (5)
C18'—C19'—C20'—C25	−48.8 (10)	C28—C27—C32—C31	0.0 (4)
C8—C7—C21—C22	−58.1 (2)	C23—C27—C32—C31	−178.5 (2)
C12—C7—C21—C22	121.1 (2)	C30—C31—C32—C27	−1.8 (4)
C8—C7—C21—C26	119.3 (2)

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈ClO₃P
M_r	526.96
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	12.6642 (8), 13.1613 (8), 15.9097 (9)
V (Å³)	2651.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.32 × 0.17 × 0.07

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	33491, 6089, 4949
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.03
No. of reflections	6089
No. of parameters	370
No. of restraints	52
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23
Absolute structure	Flack (1983), 2674 Friedel pairs
Absolute structure parameter	0.02 (6)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006 or??2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

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(R)-3,3'-Diphenyl-5,6,7,8,5',6',7',8'-octa­hydro-1,1'-binaphthyl-2,2'-diyl chloro­phosphate