(2R,4S,5R)-3,4-Di­methyl-5-phenyl-2-[4-(tri­fluoro­methyl)­phenyl]-1,3,2-ox­aza­phospho­lidine(P-B)­borane

A P-chiral phosphinite borane complex, C₁₇H₂₀BF₃NOP, derived from (2R,4S,5R)-2-chloro-3,4-di­methyl-5-phenyl-1,3,2-ox­aza­phospho­lidine and [4-(tri­fluoro­methyl)­phenyl]­magnesium bromide is reported. The absolute configuration (R at P) is deduced from the known chirality of (1R,2S)-ephedrine and confirmed by the refinement.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.134
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....         F1
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....         C7

Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        F1'
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         F3
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        F3'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.

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           27.03
           From the CIF: _reflns_number_total               4085
           Count of symmetry unique reflns         2339
           Completeness (_total/calc)            174.65%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1746
           Fraction of Friedel pairs measured     0.746
           Are heavy atom types Z>Si present          yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C17H20BF3NOP	F(000) = 736
Mr = 353.13	Dx = 1.254 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.1911 (16) Å	θ = 37.7–49.6°
b = 12.8581 (17) Å	µ = 0.18 mm^−1
c = 15.827 (2) Å	T = 293 K
V = 1870.4 (5) Å^3	Rod, colourless
Z = 4	1.00 × 0.75 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	θmax = 27.0°, θmin = 3.0°
non–profiled ω/2θ scans	h = −11→4
6482 measured reflections	k = −16→16
4085 independent reflections	l = −20→0
2990 reflections with I > 2σ(I)	2 standard reflections every 123 reflections
Rint = 0.023	intensity decay: 4%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0841P)^2 + 0.0091P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.048	(Δ/σ)max < 0.001
wR(F^2) = 0.134	Δρmax = 0.20 e Å^−3
S = 1.04	Δρmin = −0.39 e Å^−3
4085 reflections	Absolute structure: Flack (1983), 1755 Friedel pairs
244 parameters	Absolute structure parameter: 0.04 (12)
6 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	Occ. (<1)
P1	0.05132 (7)	0.41982 (4)	0.24575 (4)	0.05432 (18)
F1	0.1096 (10)	0.1783 (10)	0.6142 (7)	0.170 (6)	0.50
F2	−0.1108 (10)	0.1924 (11)	0.6150 (5)	0.136 (3)	0.50
F3	0.0151 (15)	0.3200 (7)	0.6588 (4)	0.144 (5)	0.50
F1'	−0.1285 (9)	0.2635 (10)	0.6340 (6)	0.150 (4)	0.50
F2'	0.0946 (12)	0.2859 (8)	0.6566 (6)	0.128 (3)	0.50
F3'	0.030 (2)	0.1475 (4)	0.6103 (4)	0.155 (5)	0.50
O1	0.0408 (2)	0.32031 (11)	0.18536 (10)	0.0609 (4)
N1	−0.1053 (3)	0.47199 (15)	0.21583 (13)	0.0645 (6)
C1	0.0358 (3)	0.36700 (18)	0.35136 (14)	0.0554 (6)
C2	0.0774 (3)	0.4256 (2)	0.42013 (16)	0.0687 (7)
H2	0.1135	0.4924	0.4116	0.082*
C3	0.0665 (4)	0.3875 (2)	0.50128 (16)	0.0721 (8)
H3	0.0941	0.4284	0.5470	0.087*
C4	0.0148 (3)	0.2887 (2)	0.51408 (16)	0.0649 (7)
C5	−0.0272 (4)	0.2288 (2)	0.44695 (17)	0.0813 (9)
H5	−0.0610	0.1615	0.4560	0.098*
C6	−0.0194 (4)	0.2677 (2)	0.36593 (16)	0.0753 (8)
H6	−0.0512	0.2274	0.3207	0.090*
C7	0.0032 (4)	0.2464 (3)	0.60206 (18)	0.0868 (10)
C8	−0.1713 (4)	0.5531 (2)	0.2686 (2)	0.0953 (10)
H8A	−0.2610	0.5756	0.2435	0.143*
H8B	−0.1058	0.6110	0.2729	0.143*
H8C	−0.1901	0.5257	0.3240	0.143*
C9	−0.3173 (4)	0.4336 (3)	0.1247 (3)	0.1084 (12)
H9A	−0.3770	0.4821	0.1552	0.163*
H9B	−0.3767	0.3778	0.1038	0.163*
H9C	−0.2716	0.4685	0.0781	0.163*
C10	−0.2013 (3)	0.3901 (2)	0.18314 (19)	0.0748 (8)
H10	−0.2493	0.3560	0.2310	0.090*
C11	−0.0975 (3)	0.3114 (2)	0.14096 (17)	0.0652 (7)
H11	−0.1360	0.2413	0.1508	0.078*
C12	−0.0717 (3)	0.32381 (19)	0.04783 (16)	0.0635 (6)
C13	0.0167 (3)	0.4010 (2)	0.01573 (17)	0.0714 (8)
H13	0.0623	0.4469	0.0526	0.086*
C14	0.0386 (4)	0.4112 (3)	−0.06980 (19)	0.0904 (9)
H14	0.0971	0.4647	−0.0901	0.108*
C15	−0.0243 (5)	0.3440 (4)	−0.1250 (2)	0.1023 (13)
H15	−0.0060	0.3496	−0.1826	0.123*
C16	−0.1139 (5)	0.2690 (3)	−0.0955 (2)	0.1077 (13)
H16	−0.1605	0.2249	−0.1334	0.129*
C17	−0.1374 (4)	0.2567 (3)	−0.0087 (2)	0.0940 (10)
H17	−0.1971	0.2035	0.0109	0.113*
B1	0.2156 (4)	0.5058 (3)	0.2312 (2)	0.0725 (8)
H1A	0.3016	0.4684	0.2473	0.109*
H1B	0.2059	0.5667	0.2658	0.109*
H1C	0.2230	0.5261	0.1729	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0666 (3)	0.0457 (3)	0.0507 (3)	0.0024 (3)	0.0073 (3)	0.0026 (3)
F1	0.147 (6)	0.224 (13)	0.138 (7)	−0.009 (7)	−0.024 (5)	0.120 (8)
F2	0.135 (6)	0.187 (8)	0.088 (4)	−0.079 (6)	−0.005 (4)	0.062 (6)
F3	0.262 (14)	0.127 (6)	0.043 (2)	−0.039 (7)	0.009 (5)	−0.003 (3)
F1'	0.147 (7)	0.198 (8)	0.104 (5)	0.006 (7)	0.057 (5)	0.048 (6)
F2'	0.173 (8)	0.125 (7)	0.086 (4)	−0.059 (5)	−0.044 (5)	0.031 (4)
F3'	0.311 (16)	0.070 (3)	0.083 (3)	−0.010 (6)	0.028 (7)	0.019 (2)
O1	0.0793 (11)	0.0510 (8)	0.0525 (8)	0.0086 (9)	−0.0004 (9)	−0.0012 (7)
N1	0.0738 (14)	0.0513 (11)	0.0682 (12)	0.0075 (10)	0.0073 (11)	0.0064 (9)
C1	0.0690 (15)	0.0483 (11)	0.0488 (10)	−0.0034 (12)	0.0047 (11)	0.0009 (9)
C2	0.0896 (19)	0.0548 (13)	0.0616 (13)	−0.0182 (14)	0.0066 (13)	−0.0028 (12)
C3	0.093 (2)	0.0718 (16)	0.0515 (11)	−0.0218 (16)	−0.0011 (14)	−0.0073 (11)
C4	0.0742 (17)	0.0688 (15)	0.0517 (12)	−0.0075 (13)	0.0029 (12)	0.0049 (11)
C5	0.126 (3)	0.0550 (13)	0.0633 (14)	−0.0239 (17)	0.0016 (17)	0.0055 (11)
C6	0.119 (3)	0.0536 (13)	0.0532 (13)	−0.0141 (16)	−0.0066 (15)	−0.0020 (11)
C7	0.113 (3)	0.090 (2)	0.0581 (16)	−0.017 (2)	−0.0014 (18)	0.0086 (15)
C8	0.105 (2)	0.0764 (17)	0.105 (2)	0.0320 (18)	0.019 (2)	−0.0066 (17)
C9	0.0689 (19)	0.132 (3)	0.124 (3)	0.020 (2)	−0.012 (2)	−0.008 (3)
C10	0.0678 (17)	0.0783 (17)	0.0784 (17)	−0.0067 (14)	0.0098 (14)	0.0081 (14)
C11	0.0796 (17)	0.0497 (12)	0.0664 (15)	−0.0126 (13)	−0.0012 (13)	0.0070 (11)
C12	0.0704 (16)	0.0556 (13)	0.0644 (13)	−0.0005 (13)	−0.0140 (13)	−0.0011 (11)
C13	0.085 (2)	0.0698 (16)	0.0592 (13)	−0.0050 (15)	−0.0016 (13)	0.0044 (12)
C14	0.099 (2)	0.107 (2)	0.0650 (15)	0.017 (2)	0.0038 (16)	0.0227 (17)
C15	0.108 (3)	0.140 (3)	0.0588 (17)	0.039 (3)	−0.0159 (19)	−0.003 (2)
C16	0.118 (3)	0.125 (3)	0.080 (2)	0.007 (3)	−0.040 (2)	−0.030 (2)
C17	0.104 (3)	0.090 (2)	0.089 (2)	−0.014 (2)	−0.024 (2)	−0.0120 (17)
B1	0.082 (2)	0.0703 (16)	0.0656 (18)	−0.0192 (16)	0.0020 (15)	0.0076 (14)

Geometric parameters (Å, º)

P1—O1	1.6001 (16)	C8—H8B	0.96
P1—N1	1.657 (2)	C8—H8C	0.96
P1—C1	1.810 (2)	C9—C10	1.519 (5)
P1—B1	1.886 (3)	C9—H9A	0.96
F1—C7	1.327 (7)	C9—H9B	0.96
F2—C7	1.274 (6)	C9—H9C	0.96
F3—C7	1.308 (7)	C10—C11	1.543 (4)
F1'—C7	1.330 (7)	C10—H10	0.98
F2'—C7	1.307 (7)	C11—C12	1.501 (4)
F3'—C7	1.302 (6)	C11—H11	0.98
O1—C11	1.457 (3)	C12—C13	1.380 (4)
N1—C8	1.467 (3)	C12—C17	1.382 (4)
N1—C10	1.468 (3)	C13—C14	1.375 (4)
C1—C2	1.378 (3)	C13—H13	0.93
C1—C6	1.394 (4)	C14—C15	1.358 (5)
C2—C3	1.378 (3)	C14—H14	0.93
C2—H2	0.93	C15—C16	1.351 (6)
C3—C4	1.372 (4)	C15—H15	0.93
C3—H3	0.93	C16—C17	1.400 (6)
C4—C5	1.368 (4)	C16—H16	0.93
C4—C7	1.498 (4)	C17—H17	0.93
C5—C6	1.378 (4)	B1—H1A	0.96
C5—H5	0.93	B1—H1B	0.96
C6—H6	0.93	B1—H1C	0.96
C8—H8A	0.96
O1—P1—N1	95.76 (10)	N1—C8—H8C	109.5
O1—P1—C1	104.29 (10)	H8A—C8—H8C	109.5
N1—P1—C1	110.33 (11)	H8B—C8—H8C	109.5
O1—P1—B1	116.36 (14)	C10—C9—H9A	109.5
N1—P1—B1	115.05 (14)	C10—C9—H9B	109.5
C1—P1—B1	113.34 (14)	H9A—C9—H9B	109.5
C11—O1—P1	113.84 (16)	C10—C9—H9C	109.5
C8—N1—C10	117.5 (3)	H9A—C9—H9C	109.5
C8—N1—P1	118.9 (2)	H9B—C9—H9C	109.5
C10—N1—P1	109.42 (16)	N1—C10—C9	111.9 (3)
C2—C1—C6	118.1 (2)	N1—C10—C11	104.6 (2)
C2—C1—P1	120.16 (18)	C9—C10—C11	114.3 (3)
C6—C1—P1	121.70 (18)	N1—C10—H10	108.6
C1—C2—C3	121.4 (2)	C9—C10—H10	108.6
C1—C2—H2	119.3	C11—C10—H10	108.6
C3—C2—H2	119.3	O1—C11—C12	109.1 (2)
C4—C3—C2	119.5 (2)	O1—C11—C10	106.2 (2)
C4—C3—H3	120.3	C12—C11—C10	116.9 (2)
C2—C3—H3	120.3	O1—C11—H11	108.1
C5—C4—C3	120.3 (2)	C12—C11—H11	108.1
C5—C4—C7	119.9 (2)	C10—C11—H11	108.1
C3—C4—C7	119.8 (2)	C13—C12—C17	117.9 (3)
C4—C5—C6	120.2 (2)	C13—C12—C11	122.1 (2)
C4—C5—H5	119.9	C17—C12—C11	120.0 (3)
C6—C5—H5	119.9	C14—C13—C12	121.2 (3)
C5—C6—C1	120.4 (2)	C14—C13—H13	119.4
C5—C6—H6	119.8	C12—C13—H13	119.4
C1—C6—H6	119.8	C15—C14—C13	120.6 (4)
F2—C7—F2'	129.4 (6)	C15—C14—H14	119.7
F3'—C7—F2'	101.1 (7)	C13—C14—H14	119.7
F2—C7—F3	110.7 (7)	C16—C15—C14	119.5 (3)
F3'—C7—F3	128.4 (6)	C16—C15—H15	120.3
F2—C7—F1	102.9 (6)	C14—C15—H15	120.3
F3—C7—F1	108.4 (7)	C15—C16—C17	120.9 (3)
F3'—C7—F1'	107.2 (6)	C15—C16—H16	119.5
F2'—C7—F1'	105.6 (7)	C17—C16—H16	119.5
F1—C7—F1'	136.4 (5)	C12—C17—C16	119.8 (4)
F2—C7—C4	113.9 (4)	C12—C17—H17	120.1
F3'—C7—C4	115.7 (4)	C16—C17—H17	120.1
F2'—C7—C4	115.3 (5)	P1—B1—H1A	109.5
F3—C7—C4	111.7 (5)	P1—B1—H1B	109.5
F1—C7—C4	108.8 (5)	H1A—B1—H1B	109.5
F1'—C7—C4	111.0 (5)	P1—B1—H1C	109.5
N1—C8—H8A	109.5	H1A—B1—H1C	109.5
N1—C8—H8B	109.5	H1B—B1—H1C	109.5
H8A—C8—H8B	109.5
N1—P1—O1—C11	−6.50 (17)	C3—C4—C7—F2'	−27.1 (8)
C1—P1—O1—C11	106.20 (17)	C5—C4—C7—F3	−165.3 (7)
B1—P1—O1—C11	−128.16 (19)	C3—C4—C7—F3	14.3 (8)
O1—P1—N1—C8	163.5 (2)	C5—C4—C7—F1	75.0 (8)
C1—P1—N1—C8	55.9 (2)	C3—C4—C7—F1	−105.4 (8)
B1—P1—N1—C8	−73.8 (2)	C5—C4—C7—F1'	−86.7 (8)
O1—P1—N1—C10	24.48 (18)	C3—C4—C7—F1'	92.9 (7)
C1—P1—N1—C10	−83.09 (19)	C8—N1—C10—C9	62.7 (3)
B1—P1—N1—C10	147.15 (19)	P1—N1—C10—C9	−157.6 (2)
O1—P1—C1—C2	163.2 (2)	C8—N1—C10—C11	−173.0 (2)
N1—P1—C1—C2	−95.0 (2)	P1—N1—C10—C11	−33.3 (2)
B1—P1—C1—C2	35.7 (3)	P1—O1—C11—C12	114.57 (19)
O1—P1—C1—C6	−17.6 (3)	P1—O1—C11—C10	−12.2 (2)
N1—P1—C1—C6	84.2 (3)	N1—C10—C11—O1	27.9 (2)
B1—P1—C1—C6	−145.1 (3)	C9—C10—C11—O1	150.6 (3)
C6—C1—C2—C3	0.7 (5)	N1—C10—C11—C12	−94.1 (3)
P1—C1—C2—C3	179.9 (3)	C9—C10—C11—C12	28.7 (4)
C1—C2—C3—C4	0.7 (5)	O1—C11—C12—C13	−44.9 (3)
C2—C3—C4—C5	−0.7 (5)	C10—C11—C12—C13	75.6 (4)
C2—C3—C4—C7	179.7 (3)	O1—C11—C12—C17	135.0 (3)
C3—C4—C5—C6	−0.8 (6)	C10—C11—C12—C17	−104.5 (3)
C7—C4—C5—C6	178.8 (3)	C17—C12—C13—C14	0.3 (4)
C4—C5—C6—C1	2.2 (6)	C11—C12—C13—C14	−179.8 (3)
C2—C1—C6—C5	−2.1 (5)	C12—C13—C14—C15	−1.3 (5)
P1—C1—C6—C5	178.7 (3)	C13—C14—C15—C16	2.6 (6)
C5—C4—C7—F2	−39.0 (10)	C14—C15—C16—C17	−2.9 (6)
C3—C4—C7—F2	140.6 (9)	C13—C12—C17—C16	−0.5 (5)
C5—C4—C7—F3'	35.6 (11)	C11—C12—C17—C16	179.6 (3)
C3—C4—C7—F3'	−144.8 (10)	C15—C16—C17—C12	1.9 (6)
C5—C4—C7—F2'	153.3 (7)