1,1'-Binaphthyl-2,2'-diyl benzyl-phos-phoramidate.

In the title compound, C(27)H(20)NO(3)P, the P atom exhibits a somewhat distorted PNO(3) tetra-hedral geometry, with the O-P-O angle for the binaphthyl fragment being 102.82 (6)°. The dihedral angle between the naphthyl ring systems is 59.00 (2)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For background to organo­phospho­rus chemistry, see: Malik et al. (2010 ▶). For related structures, see: Gowda et al. (2010a ▶,b ▶, 2011 ▶).

Experimental

Crystal data

C27H20NO3P

M = 437.41

Monoclinic,

a = 13.7998 (4) Å

b = 11.0667 (3) Å

c = 14.7487 (5) Å

β = 112.674 (1)°

V = 2078.31 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 298 K

0.35 × 0.27 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.945, T max = 0.965

29246 measured reflections

5053 independent reflections

3766 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.03

5053 reflections

293 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046861/hb6484sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046861/hb6484Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046861/hb6484Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H20NO3P	F(000) = 912
Mr = 437.41	Dx = 1.398 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9423 reflections
a = 13.7998 (4) Å	θ = 2.4–28.1°
b = 11.0667 (3) Å	µ = 0.16 mm−1
c = 14.7487 (5) Å	T = 298 K
β = 112.674 (1)°	Block, colourless
V = 2078.31 (11) Å3	0.35 × 0.27 × 0.22 mm
Z = 4

Bruker APEXII CCD diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	3766 reflections with I > 2σ(I)
graphite	Rint = 0.053
phi and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→18
Tmin = 0.945, Tmax = 0.965	k = −14→14
29246 measured reflections	l = −17→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.951P] where P = (Fo2 + 2Fc2)/3
5053 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1	0.32299 (11)	0.67344 (13)	0.54067 (11)	0.0203 (3)
C2	0.40314 (13)	0.62679 (14)	0.62471 (12)	0.0265 (4)
H2	0.3893	0.6035	0.6791	0.032*
C3	0.50170 (13)	0.61628 (14)	0.62505 (13)	0.0295 (4)
H3	0.5561	0.5897	0.6817	0.035*
C4	0.52293 (12)	0.64488 (13)	0.54141 (13)	0.0260 (4)
C5	0.62343 (13)	0.62768 (15)	0.53816 (15)	0.0354 (4)
H5	0.6783	0.5996	0.5938	0.042*
C6	0.64113 (14)	0.65125 (16)	0.45568 (17)	0.0399 (5)
H6	0.7078	0.6402	0.4553	0.048*
C7	0.55859 (14)	0.69235 (15)	0.37079 (16)	0.0363 (4)
H7	0.5705	0.7067	0.3138	0.044*
C8	0.46115 (13)	0.71132 (14)	0.37106 (13)	0.0275 (4)
H8	0.4074	0.7382	0.3141	0.033*
C9	0.44037 (12)	0.69088 (13)	0.45658 (12)	0.0221 (3)
C10	0.33940 (11)	0.71257 (13)	0.45942 (11)	0.0192 (3)
C11	0.25437 (12)	0.77459 (13)	0.37799 (11)	0.0190 (3)
C12	0.26774 (12)	0.89308 (13)	0.34438 (11)	0.0204 (3)
C13	0.36253 (13)	0.95968 (14)	0.38600 (12)	0.0236 (3)
H13	0.4200	0.9252	0.4357	0.028*
C14	0.37069 (14)	1.07407 (14)	0.35407 (13)	0.0291 (4)
H14	0.4338	1.1158	0.3817	0.035*
C15	0.28496 (15)	1.12864 (15)	0.28029 (13)	0.0339 (4)
H15	0.2910	1.2069	0.2600	0.041*
C16	0.19313 (15)	1.06775 (16)	0.23828 (13)	0.0318 (4)
H16	0.1368	1.1046	0.1889	0.038*
C17	0.18144 (13)	0.94851 (15)	0.26850 (11)	0.0245 (3)
C18	0.08507 (13)	0.88577 (16)	0.22596 (12)	0.0294 (4)
H18	0.0297	0.9207	0.1743	0.035*
C19	0.07260 (12)	0.77502 (16)	0.25975 (12)	0.0269 (4)
H19	0.0088	0.7345	0.2322	0.032*
C20	0.15695 (12)	0.72271 (14)	0.33655 (11)	0.0211 (3)
C21	0.02951 (13)	0.81676 (14)	0.48691 (14)	0.0313 (4)
H21A	0.0745	0.8546	0.4583	0.038*
H21B	0.0593	0.8325	0.5570	0.038*
C22	−0.07845 (12)	0.87219 (13)	0.44285 (12)	0.0246 (3)
C23	−0.11269 (14)	0.93190 (15)	0.35337 (13)	0.0305 (4)
H23	−0.0699	0.9341	0.3177	0.037*
C24	−0.20985 (15)	0.98832 (16)	0.31637 (14)	0.0360 (4)
H24	−0.2317	1.0285	0.2564	0.043*
C25	−0.27378 (14)	0.98487 (16)	0.36827 (15)	0.0376 (4)
H25	−0.3385	1.0238	0.3441	0.045*
C26	−0.24159 (15)	0.92352 (18)	0.45635 (15)	0.0397 (5)
H26	−0.2853	0.9195	0.4910	0.048*
C27	−0.14467 (15)	0.86821 (17)	0.49314 (14)	0.0341 (4)
H27	−0.1235	0.8275	0.5528	0.041*
N1	0.02726 (10)	0.68495 (11)	0.47013 (10)	0.0239 (3)
O1	0.22318 (8)	0.68401 (9)	0.54441 (8)	0.0220 (2)
O2	0.14012 (8)	0.61001 (9)	0.37169 (8)	0.0229 (2)
O3	0.12166 (8)	0.47812 (10)	0.49874 (8)	0.0260 (3)
P1	0.12654 (3)	0.60554 (3)	0.47454 (3)	0.02003 (11)
H1N	−0.0227 (15)	0.6422 (19)	0.4812 (14)	0.038 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0176 (7)	0.0159 (7)	0.0252 (8)	−0.0039 (6)	0.0057 (6)	−0.0015 (6)
C2	0.0310 (9)	0.0196 (8)	0.0227 (8)	−0.0038 (6)	0.0034 (7)	0.0014 (6)
C3	0.0241 (8)	0.0191 (8)	0.0323 (9)	0.0010 (6)	−0.0035 (7)	0.0011 (7)
C4	0.0186 (8)	0.0136 (7)	0.0391 (10)	−0.0006 (6)	0.0036 (7)	−0.0023 (6)
C5	0.0185 (8)	0.0198 (8)	0.0578 (13)	0.0015 (6)	0.0036 (8)	−0.0051 (8)
C6	0.0227 (9)	0.0240 (9)	0.0775 (15)	0.0011 (7)	0.0242 (10)	−0.0060 (9)
C7	0.0344 (10)	0.0246 (9)	0.0605 (13)	0.0016 (7)	0.0300 (10)	0.0000 (8)
C8	0.0256 (8)	0.0188 (7)	0.0418 (10)	0.0011 (6)	0.0170 (8)	0.0013 (7)
C9	0.0187 (7)	0.0118 (7)	0.0345 (9)	−0.0016 (5)	0.0086 (7)	−0.0006 (6)
C10	0.0159 (7)	0.0132 (6)	0.0254 (8)	−0.0021 (5)	0.0046 (6)	−0.0006 (6)
C11	0.0186 (7)	0.0193 (7)	0.0199 (8)	0.0012 (6)	0.0084 (6)	−0.0009 (6)
C12	0.0232 (8)	0.0202 (7)	0.0206 (8)	0.0030 (6)	0.0117 (6)	0.0005 (6)
C13	0.0252 (8)	0.0191 (7)	0.0270 (8)	0.0017 (6)	0.0107 (7)	0.0007 (6)
C14	0.0363 (10)	0.0205 (8)	0.0348 (10)	−0.0020 (7)	0.0184 (8)	−0.0001 (7)
C15	0.0505 (11)	0.0200 (8)	0.0386 (10)	0.0051 (7)	0.0253 (9)	0.0085 (7)
C16	0.0402 (10)	0.0290 (9)	0.0283 (9)	0.0129 (8)	0.0154 (8)	0.0106 (7)
C17	0.0284 (9)	0.0268 (8)	0.0207 (8)	0.0066 (7)	0.0119 (7)	0.0026 (6)
C18	0.0251 (9)	0.0401 (10)	0.0205 (8)	0.0085 (7)	0.0058 (7)	0.0056 (7)
C19	0.0177 (8)	0.0394 (9)	0.0206 (8)	−0.0018 (7)	0.0042 (7)	−0.0033 (7)
C20	0.0213 (8)	0.0230 (8)	0.0201 (8)	−0.0009 (6)	0.0092 (6)	−0.0015 (6)
C21	0.0251 (9)	0.0191 (8)	0.0465 (11)	−0.0031 (6)	0.0103 (8)	−0.0062 (7)
C22	0.0234 (8)	0.0166 (7)	0.0339 (9)	−0.0039 (6)	0.0113 (7)	−0.0057 (6)
C23	0.0343 (10)	0.0269 (8)	0.0359 (10)	−0.0052 (7)	0.0199 (8)	−0.0038 (7)
C24	0.0378 (10)	0.0290 (9)	0.0346 (10)	−0.0013 (8)	0.0067 (8)	0.0018 (8)
C25	0.0254 (9)	0.0303 (9)	0.0520 (12)	0.0013 (7)	0.0094 (9)	−0.0099 (8)
C26	0.0347 (10)	0.0425 (11)	0.0517 (12)	−0.0045 (8)	0.0274 (10)	−0.0111 (9)
C27	0.0376 (10)	0.0350 (10)	0.0339 (10)	−0.0020 (8)	0.0184 (8)	0.0005 (8)
N1	0.0208 (7)	0.0167 (6)	0.0358 (8)	−0.0038 (5)	0.0125 (6)	−0.0014 (5)
O1	0.0190 (5)	0.0248 (5)	0.0214 (6)	−0.0063 (4)	0.0068 (5)	−0.0028 (4)
O2	0.0223 (6)	0.0207 (5)	0.0254 (6)	−0.0069 (4)	0.0089 (5)	−0.0045 (4)
O3	0.0214 (6)	0.0200 (5)	0.0367 (7)	−0.0016 (4)	0.0114 (5)	0.0020 (5)
P1	0.0170 (2)	0.01769 (19)	0.0248 (2)	−0.00387 (14)	0.00742 (16)	−0.00084 (15)

C1—C10	1.373 (2)	C16—C17	1.422 (2)
C1—C2	1.403 (2)	C16—H16	0.9300
C1—O1	1.4043 (18)	C17—C18	1.415 (2)
C2—C3	1.363 (2)	C18—C19	1.359 (2)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.409 (3)	C19—C20	1.399 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.419 (2)	C20—O2	1.4039 (18)
C4—C9	1.422 (2)	C21—N1	1.4778 (19)
C5—C6	1.355 (3)	C21—C22	1.507 (2)
C5—H5	0.9300	C21—H21A	0.9700
C6—C7	1.404 (3)	C21—H21B	0.9700
C6—H6	0.9300	C22—C27	1.382 (2)
C7—C8	1.362 (2)	C22—C23	1.386 (2)
C7—H7	0.9300	C23—C24	1.386 (3)
C8—C9	1.415 (2)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.373 (3)
C9—C10	1.430 (2)	C24—H24	0.9300
C10—C11	1.485 (2)	C25—C26	1.379 (3)
C11—C20	1.370 (2)	C25—H25	0.9300
C11—C12	1.439 (2)	C26—C27	1.378 (3)
C12—C13	1.418 (2)	C26—H26	0.9300
C12—C17	1.421 (2)	C27—H27	0.9300
C13—C14	1.370 (2)	N1—P1	1.6078 (14)
C13—H13	0.9300	N1—H1N	0.90 (2)
C14—C15	1.399 (2)	O1—P1	1.5921 (11)
C14—H14	0.9300	O2—P1	1.5992 (11)
C15—C16	1.356 (3)	O3—P1	1.4625 (11)
C15—H15	0.9300
C10—C1—C2	123.23 (14)	C18—C17—C12	119.77 (14)
C10—C1—O1	120.16 (13)	C18—C17—C16	121.16 (15)
C2—C1—O1	116.56 (14)	C12—C17—C16	119.05 (15)
C3—C2—C1	118.71 (16)	C19—C18—C17	120.69 (15)
C3—C2—H2	120.6	C19—C18—H18	119.7
C1—C2—H2	120.6	C17—C18—H18	119.7
C2—C3—C4	121.42 (15)	C18—C19—C20	119.13 (15)
C2—C3—H3	119.3	C18—C19—H19	120.4
C4—C3—H3	119.3	C20—C19—H19	120.4
C3—C4—C5	122.35 (16)	C11—C20—C19	123.71 (14)
C3—C4—C9	118.95 (14)	C11—C20—O2	118.75 (13)
C5—C4—C9	118.69 (16)	C19—C20—O2	117.53 (13)
C6—C5—C4	121.42 (17)	N1—C21—C22	112.09 (13)
C6—C5—H5	119.3	N1—C21—H21A	109.2
C4—C5—H5	119.3	C22—C21—H21A	109.2
C5—C6—C7	119.85 (16)	N1—C21—H21B	109.2
C5—C6—H6	120.1	C22—C21—H21B	109.2
C7—C6—H6	120.1	H21A—C21—H21B	107.9
C8—C7—C6	120.63 (18)	C27—C22—C23	118.23 (16)
C8—C7—H7	119.7	C27—C22—C21	120.26 (16)
C6—C7—H7	119.7	C23—C22—C21	121.47 (15)
C7—C8—C9	121.15 (17)	C22—C23—C24	120.85 (16)
C7—C8—H8	119.4	C22—C23—H23	119.6
C9—C8—H8	119.4	C24—C23—H23	119.6
C8—C9—C4	118.19 (14)	C25—C24—C23	119.98 (18)
C8—C9—C10	122.24 (14)	C25—C24—H24	120.0
C4—C9—C10	119.56 (14)	C23—C24—H24	120.0
C1—C10—C9	117.58 (14)	C24—C25—C26	119.73 (17)
C1—C10—C11	120.47 (13)	C24—C25—H25	120.1
C9—C10—C11	121.94 (13)	C26—C25—H25	120.1
C20—C11—C12	117.54 (14)	C27—C26—C25	120.07 (17)
C20—C11—C10	120.06 (13)	C27—C26—H26	120.0
C12—C11—C10	122.26 (13)	C25—C26—H26	120.0
C13—C12—C17	118.00 (14)	C26—C27—C22	121.12 (18)
C13—C12—C11	122.95 (14)	C26—C27—H27	119.4
C17—C12—C11	119.01 (14)	C22—C27—H27	119.4
C14—C13—C12	121.03 (15)	C21—N1—P1	124.76 (11)
C14—C13—H13	119.5	C21—N1—H1N	117.2 (13)
C12—C13—H13	119.5	P1—N1—H1N	113.9 (13)
C13—C14—C15	120.62 (16)	C1—O1—P1	121.24 (9)
C13—C14—H14	119.7	C20—O2—P1	118.31 (9)
C15—C14—H14	119.7	O3—P1—O1	118.28 (6)
C16—C15—C14	120.15 (15)	O3—P1—O2	107.13 (6)
C16—C15—H15	119.9	O1—P1—O2	102.82 (6)
C14—C15—H15	119.9	O3—P1—N1	114.72 (7)
C15—C16—C17	121.13 (16)	O1—P1—N1	102.49 (7)
C15—C16—H16	119.4	O2—P1—N1	110.75 (7)
C17—C16—H16	119.4
C10—C1—C2—C3	−2.0 (2)	C11—C12—C17—C18	−1.4 (2)
O1—C1—C2—C3	−179.17 (13)	C13—C12—C17—C16	−0.6 (2)
C1—C2—C3—C4	−3.5 (2)	C11—C12—C17—C16	177.21 (14)
C2—C3—C4—C5	−176.09 (15)	C15—C16—C17—C18	178.83 (16)
C2—C3—C4—C9	2.9 (2)	C15—C16—C17—C12	0.3 (2)
C3—C4—C5—C6	177.34 (16)	C12—C17—C18—C19	2.9 (2)
C9—C4—C5—C6	−1.7 (2)	C16—C17—C18—C19	−175.69 (15)
C4—C5—C6—C7	−0.7 (3)	C17—C18—C19—C20	−0.9 (2)
C5—C6—C7—C8	1.4 (3)	C12—C11—C20—C19	4.2 (2)
C6—C7—C8—C9	0.3 (3)	C10—C11—C20—C19	179.94 (14)
C7—C8—C9—C4	−2.7 (2)	C12—C11—C20—O2	−176.58 (12)
C7—C8—C9—C10	178.63 (15)	C10—C11—C20—O2	−0.8 (2)
C3—C4—C9—C8	−175.75 (14)	C18—C19—C20—C11	−2.8 (2)
C5—C4—C9—C8	3.3 (2)	C18—C19—C20—O2	177.96 (14)
C3—C4—C9—C10	3.0 (2)	N1—C21—C22—C27	82.3 (2)
C5—C4—C9—C10	−177.98 (14)	N1—C21—C22—C23	−100.01 (18)
C2—C1—C10—C9	7.7 (2)	C27—C22—C23—C24	1.4 (2)
O1—C1—C10—C9	−175.23 (12)	C21—C22—C23—C24	−176.33 (15)
C2—C1—C10—C11	−172.53 (14)	C22—C23—C24—C25	−0.4 (3)
O1—C1—C10—C11	4.6 (2)	C23—C24—C25—C26	−1.0 (3)
C8—C9—C10—C1	170.66 (14)	C24—C25—C26—C27	1.4 (3)
C4—C9—C10—C1	−8.0 (2)	C25—C26—C27—C22	−0.4 (3)
C8—C9—C10—C11	−9.1 (2)	C23—C22—C27—C26	−1.0 (3)
C4—C9—C10—C11	172.19 (13)	C21—C22—C27—C26	176.76 (16)
C1—C10—C11—C20	−51.9 (2)	C22—C21—N1—P1	159.02 (12)
C9—C10—C11—C20	127.90 (15)	C10—C1—O1—P1	68.19 (16)
C1—C10—C11—C12	123.65 (16)	C2—C1—O1—P1	−114.53 (13)
C9—C10—C11—C12	−56.6 (2)	C11—C20—O2—P1	76.15 (16)
C20—C11—C12—C13	175.66 (14)	C19—C20—O2—P1	−104.58 (14)
C10—C11—C12—C13	0.0 (2)	C1—O1—P1—O3	76.30 (12)
C20—C11—C12—C17	−2.0 (2)	C1—O1—P1—O2	−41.44 (12)
C10—C11—C12—C17	−177.66 (14)	C1—O1—P1—N1	−156.43 (11)
C17—C12—C13—C14	0.0 (2)	C20—O2—P1—O3	−173.99 (10)
C11—C12—C13—C14	−177.67 (15)	C20—O2—P1—O1	−48.64 (11)
C12—C13—C14—C15	0.8 (2)	C20—O2—P1—N1	60.22 (12)
C13—C14—C15—C16	−1.2 (3)	C21—N1—P1—O3	154.28 (14)
C14—C15—C16—C17	0.6 (3)	C21—N1—P1—O1	24.77 (16)
C13—C12—C17—C18	−179.16 (14)	C21—N1—P1—O2	−84.31 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.90 (2)	2.01 (2)	2.9015 (17)	170.2 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.90 (2)	2.01 (2)	2.9015 (17)	170.2 (18)

Symmetry code: (i) .