α-[(Di­phenyl­methoxy)­methyl]-2,5-di­methyl-1-pyrrolidineethanol

The conformation of the pyrrolidine ring in the title compound, C₂₂H₂₉NO₂, is close to an envelope. The phenyl rings are almost perpendicular to one another. The mol­ecules are connected into centrosymmetric dimers by O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.116
• Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: ENPROC (Rettig, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989).

α-[(diphenylmethoxy)methyl]-2,5-dimethyl-1-pyrrolidineethanol

Crystal data

C22H29NO2	Z = 2
Mr = 339.46	F(000) = 368
Triclinic, P1	Dx = 1.102 Mg m^−3
a = 8.3588 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.6774 (4) Å	Cell parameters from 25 reflections
c = 12.5709 (5) Å	θ = 15–38°
α = 99.033 (3)°	µ = 0.54 mm^−1
β = 108.701 (4)°	T = 293 K
γ = 99.057 (3)°	Block, colourless
V = 1023.33 (7) Å^3	0.25 × 0.2 × 0.1 mm

Data collection

CAD-4F four-circle diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 3.8°
Ni-filter monochromator	h = −10→9
ω/2θ scans	k = −13→13
4207 measured reflections	l = 0→15
4207 independent reflections	2 standard reflections every 33 min
3569 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.1008P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
4207 reflections	Δρmax = 0.15 e Å^−3
333 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (6)

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.

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
C1	0.12621 (15)	0.63342 (11)	0.64278 (10)	0.0498 (3)
H1	0.2006 (17)	0.6175 (12)	0.5937 (11)	0.052 (3)*
O1	0.00007 (11)	0.51818 (9)	0.62452 (8)	0.0604 (3)
H1A	0.032 (2)	0.442 (2)	0.5899 (16)	0.104 (6)*
C2	0.03366 (18)	0.74041 (13)	0.60923 (12)	0.0585 (3)
H2A	−0.061 (2)	0.7373 (15)	0.6430 (13)	0.074 (4)*
H2B	0.113 (2)	0.8245 (16)	0.6425 (13)	0.070 (4)*
N1'	−0.04304 (14)	0.72530 (10)	0.48386 (9)	0.0597 (3)
C2'	−0.2204 (2)	0.74757 (18)	0.44440 (15)	0.0836 (5)
H2'	−0.225 (2)	0.8302 (19)	0.4974 (16)	0.100 (6)*
C2'A	−0.3519 (2)	0.6386 (3)	0.4519 (2)	0.1060 (7)
H2A1	−0.460 (4)	0.662 (2)	0.428 (2)	0.138*
H2A2	−0.322 (3)	0.623 (2)	0.536 (2)	0.138*
H2A3	−0.356 (3)	0.550 (3)	0.404 (2)	0.138*
C3'	−0.2449 (4)	0.7667 (3)	0.3223 (2)	0.1299 (10)
H3'A	−0.317 (4)	0.688 (3)	0.271 (3)	0.169*
H3'B	−0.311 (4)	0.827 (3)	0.305 (3)	0.169*
C4'	−0.0678 (4)	0.8043 (3)	0.3173 (2)	0.1191 (8)
H4'A	−0.048 (4)	0.887 (3)	0.290 (2)	0.155*
H4'B	−0.058 (4)	0.727 (3)	0.261 (2)	0.155*
C5'	0.0553 (3)	0.81798 (17)	0.43881 (16)	0.0829 (5)
H5'	0.070 (2)	0.9070 (19)	0.4838 (16)	0.096 (6)*
C5'A	0.2322 (3)	0.7938 (2)	0.4478 (2)	0.0990 (6)
H5A1	0.289 (3)	0.858 (2)	0.416 (2)	0.129*
H5A2	0.219 (3)	0.702 (2)	0.402 (2)	0.129*
H5A3	0.312 (3)	0.808 (2)	0.535 (2)	0.129*
C3	0.24192 (16)	0.66716 (12)	0.76860 (11)	0.0527 (3)
H3A	0.1724 (19)	0.6847 (14)	0.8200 (12)	0.067 (4)*
H3B	0.2967 (17)	0.5896 (13)	0.7865 (11)	0.057 (4)*
O3	0.37248 (10)	0.77970 (8)	0.78768 (7)	0.0542 (2)
C4	0.51160 (15)	0.80058 (11)	0.89443 (10)	0.0487 (3)
H4	0.4610 (17)	0.7964 (12)	0.9551 (11)	0.055 (3)*
C5	0.62687 (15)	0.93337 (11)	0.91645 (11)	0.0510 (3)
C6	0.76158 (18)	0.98014 (14)	1.02111 (13)	0.0647 (4)
H6	0.779 (2)	0.9272 (18)	1.0779 (16)	0.091 (6)*
C7	0.87581 (19)	1.09719 (15)	1.04280 (16)	0.0759 (5)
H7	0.972 (3)	1.1271 (18)	1.1206 (17)	0.100 (6)*
C8	0.8559 (2)	1.17023 (16)	0.96253 (18)	0.0821 (5)
H8	0.940 (3)	1.255 (2)	0.9783 (16)	0.108 (6)*
C9	0.7209 (3)	1.12720 (17)	0.85947 (19)	0.0943 (6)
H9	0.705 (3)	1.175 (2)	0.7998 (19)	0.123 (7)*
C10	0.6056 (2)	1.00814 (15)	0.83622 (15)	0.0764 (4)
H10	0.520 (2)	0.9773 (17)	0.7655 (16)	0.088 (5)*
C11	0.61320 (14)	0.69483 (11)	0.89154 (10)	0.0483 (3)
C12	0.65047 (19)	0.62604 (15)	0.97711 (14)	0.0684 (4)
H12	0.613 (2)	0.6487 (17)	1.0399 (15)	0.087 (5)*
C13	0.7437 (2)	0.52910 (18)	0.9704 (2)	0.0904 (6)
H13	0.769 (3)	0.486 (2)	1.0290 (18)	0.106 (6)*
C14	0.7975 (2)	0.50170 (16)	0.8800 (2)	0.0849 (5)
H14	0.865 (3)	0.434 (2)	0.8757 (17)	0.112 (6)*
C15	0.7619 (2)	0.56880 (15)	0.79497 (17)	0.0737 (4)
H15	0.802 (3)	0.548 (2)	0.7329 (18)	0.109 (7)*
C16	0.67045 (18)	0.66540 (13)	0.80075 (13)	0.0598 (3)
H16	0.643 (2)	0.7092 (17)	0.7393 (15)	0.084 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0424 (6)	0.0448 (6)	0.0540 (7)	0.0082 (5)	0.0113 (5)	0.0011 (5)
O1	0.0488 (5)	0.0495 (5)	0.0705 (6)	0.0032 (4)	0.0168 (4)	−0.0054 (4)
C2	0.0547 (7)	0.0504 (7)	0.0578 (7)	0.0171 (6)	0.0072 (6)	−0.0027 (5)
N1'	0.0558 (6)	0.0537 (6)	0.0593 (6)	0.0192 (5)	0.0071 (5)	0.0049 (5)
C2'	0.0679 (10)	0.0855 (11)	0.0805 (11)	0.0409 (9)	−0.0001 (8)	0.0027 (9)
C2'A	0.0518 (9)	0.1241 (17)	0.1181 (17)	0.0272 (10)	0.0081 (10)	−0.0020 (14)
C3'	0.127 (2)	0.157 (2)	0.0929 (16)	0.070 (2)	−0.0023 (14)	0.0416 (15)
C4'	0.134 (2)	0.128 (2)	0.0947 (16)	0.0444 (17)	0.0207 (14)	0.0505 (14)
C5'	0.1025 (13)	0.0586 (9)	0.0833 (11)	0.0194 (9)	0.0243 (10)	0.0196 (8)
C5'A	0.0922 (14)	0.0893 (13)	0.1189 (17)	0.0054 (11)	0.0473 (13)	0.0267 (12)
C3	0.0458 (6)	0.0469 (6)	0.0553 (7)	0.0036 (5)	0.0106 (5)	0.0049 (5)
O3	0.0458 (4)	0.0468 (4)	0.0554 (5)	0.0034 (3)	0.0030 (4)	0.0085 (4)
C4	0.0433 (6)	0.0504 (6)	0.0457 (6)	0.0065 (5)	0.0106 (5)	0.0059 (5)
C5	0.0448 (6)	0.0452 (6)	0.0570 (7)	0.0083 (5)	0.0158 (5)	0.0009 (5)
C6	0.0554 (7)	0.0549 (7)	0.0666 (8)	0.0096 (6)	0.0070 (6)	−0.0013 (6)
C7	0.0533 (8)	0.0558 (8)	0.0931 (12)	0.0056 (6)	0.0095 (8)	−0.0137 (8)
C8	0.0682 (9)	0.0522 (8)	0.1126 (14)	−0.0042 (7)	0.0336 (9)	−0.0048 (9)
C9	0.1097 (15)	0.0646 (10)	0.0984 (14)	−0.0060 (9)	0.0331 (12)	0.0225 (9)
C10	0.0801 (10)	0.0615 (8)	0.0689 (9)	−0.0044 (7)	0.0116 (8)	0.0128 (7)
C11	0.0409 (5)	0.0445 (6)	0.0519 (6)	0.0025 (4)	0.0098 (5)	0.0100 (5)
C12	0.0589 (8)	0.0753 (9)	0.0732 (9)	0.0110 (7)	0.0193 (7)	0.0351 (8)
C13	0.0708 (10)	0.0809 (11)	0.1244 (16)	0.0210 (9)	0.0207 (10)	0.0619 (11)
C14	0.0572 (8)	0.0571 (8)	0.1367 (17)	0.0149 (7)	0.0266 (10)	0.0251 (10)
C15	0.0606 (8)	0.0590 (8)	0.0970 (12)	0.0116 (7)	0.0303 (8)	0.0013 (8)
C16	0.0609 (8)	0.0556 (7)	0.0630 (8)	0.0149 (6)	0.0225 (6)	0.0108 (6)

Geometric parameters (Å, º)

C1—O1	1.424 (1)	C3—H3A	1.01 (1)
C1—C3	1.516 (2)	C3—H3B	1.03 (1)
C1—C2	1.517 (2)	O3—C4	1.424 (1)
C1—H1	1.02 (1)	C4—C5	1.514 (2)
O1—H1A	0.98 (2)	C4—C11	1.519 (2)
C2—N1'	1.470 (2)	C4—H4	0.99 (1)
C2—H2A	1.01 (2)	C5—C10	1.367 (2)
C2—H2B	0.97 (2)	C5—C6	1.384 (2)
N1'—C2'	1.475 (2)	C6—C7	1.378 (2)
N1'—C5'	1.481 (2)	C6—H6	0.97 (2)
C2'—C2'A	1.507 (3)	C7—C8	1.354 (3)
C2'—C3'	1.532 (3)	C7—H7	1.01 (2)
C2'—H2'	1.03 (2)	C8—C9	1.370 (3)
C2'A—H2A1	0.94 (3)	C8—H8	1.00 (2)
C2'A—H2A2	1.06 (3)	C9—C10	1.395 (2)
C2'A—H2A3	1.03 (3)	C9—H9	0.96 (2)
C3'—C4'	1.496 (4)	C10—H10	0.92 (2)
C3'—H3'A	0.95 (3)	C11—C12	1.378 (2)
C3'—H3'B	0.92 (3)	C11—C16	1.384 (2)
C4'—C5'	1.513 (3)	C12—C13	1.398 (2)
C4'—H4'A	1.00 (3)	C12—H12	0.95 (2)
C4'—H4'B	1.03 (3)	C13—C14	1.358 (3)
C5'—C5'A	1.513 (3)	C13—H13	0.91 (2)
C5'—H5'	0.99 (2)	C14—C15	1.359 (3)
C5'A—H5A1	0.99 (2)	C14—H14	0.99 (2)
C5'A—H5A2	1.02 (2)	C15—C16	1.383 (2)
C5'A—H5A3	1.05 (3)	C15—H15	0.95 (2)
C3—O3	1.422 (1)	C16—H16	0.95 (2)
O1—C1—C3	107.7 (1)	H5A2—C5'A—H5A3	112 (2)
O1—C1—C2	108.7 (1)	O3—C3—C1	108.5 (1)
C3—C1—C2	112.3 (1)	O3—C3—H3A	109.8 (8)
O1—C1—H1	110.1 (7)	C1—C3—H3A	110.7 (8)
C3—C1—H1	108.6 (7)	O3—C3—H3B	110.4 (7)
C2—C1—H1	109.5 (7)	C1—C3—H3B	108.4 (7)
C1—O1—H1A	111 (1)	H3A—C3—H3B	109 (1)
N1'—C2—C1	112.9 (1)	C3—O3—C4	112.67 (9)
N1'—C2—H2A	109.4 (9)	O3—C4—C5	108.6 (1)
C1—C2—H2A	107.1 (9)	O3—C4—C11	110.33 (9)
N1'—C2—H2B	109.2 (9)	C5—C4—C11	110.85 (9)
C1—C2—H2B	110.0 (9)	O3—C4—H4	107.6 (8)
H2A—C2—H2B	108 (1)	C5—C4—H4	110.5 (8)
C2—N1'—C2'	113.8 (1)	C11—C4—H4	108.8 (8)
C2—N1'—C5'	113.2 (1)	C10—C5—C6	118.5 (1)
C2'—N1'—C5'	104.4 (1)	C10—C5—C4	122.7 (1)
N1'—C2'—C2'A	112.5 (1)	C6—C5—C4	118.8 (1)
N1'—C2'—C3'	102.3 (2)	C7—C6—C5	121.0 (2)
C2'A—C2'—C3'	115.1 (2)	C7—C6—H6	120 (1)
N1'—C2'—H2'	109 (1)	C5—C6—H6	119 (1)
C2'A—C2'—H2'	106 (1)	C8—C7—C6	120.4 (2)
C3'—C2'—H2'	112 (1)	C8—C7—H7	122 (1)
C2'—C2'A—H2A1	107 (1)	C6—C7—H7	118 (1)
C2'—C2'A—H2A2	112 (1)	C7—C8—C9	119.5 (1)
H2A1—C2'A—H2A2	110 (2)	C7—C8—H8	120 (1)
C2'—C2'A—H2A3	113 (1)	C9—C8—H8	120 (1)
H2A1—C2'A—H2A3	111 (2)	C8—C9—C10	120.5 (2)
H2A2—C2'A—H2A3	103 (2)	C8—C9—H9	122 (1)
C4'—C3'—C2'	106.9 (2)	C10—C9—H9	118 (1)
C4'—C3'—H3'A	116 (2)	C5—C10—C9	120.1 (2)
C2'—C3'—H3'A	107 (2)	C5—C10—H10	120 (1)
C4'—C3'—H3'B	113 (2)	C9—C10—H10	120 (1)
C2'—C3'—H3'B	111 (2)	C12—C11—C16	118.4 (1)
H3'A—C3'—H3'B	103 (3)	C12—C11—C4	121.9 (1)
C3'—C4'—C5'	105.0 (2)	C16—C11—C4	119.7 (1)
C3'—C4'—H4'A	114 (2)	C11—C12—C13	119.8 (2)
C5'—C4'—H4'A	111 (2)	C11—C12—H12	118 (1)
C3'—C4'—H4'B	105 (2)	C13—C12—H12	123 (1)
C5'—C4'—H4'B	112 (2)	C14—C13—C12	120.6 (2)
H4'A—C4'—H4'B	110 (2)	C14—C13—H13	121 (1)
N1'—C5'—C4'	102.8 (2)	C12—C13—H13	118 (1)
N1'—C5'—C5'A	113.6 (1)	C13—C14—C15	120.3 (2)
C4'—C5'—C5'A	114.9 (2)	C13—C14—H14	121 (1)
N1'—C5'—H5'	108 (1)	C15—C14—H14	119 (1)
C4'—C5'—H5'	109 (1)	C14—C15—C16	119.8 (2)
C5'A—C5'—H5'	109 (1)	C14—C15—H15	119 (1)
C5'—C5'A—H5A1	109 (1)	C16—C15—H15	122 (1)
C5'—C5'A—H5A2	109 (1)	C15—C16—C11	121.2 (1)
H5A1—C5'A—H5A2	110 (2)	C15—C16—H16	119 (1)
C5'—C5'A—H5A3	111 (1)	C11—C16—H16	120 (1)
H5A1—C5'A—H5A3	107 (2)
O1—C1—C2—N1'	−75.5 (1)	C11—C4—C5—C10	113.7 (1)
C3—C1—C2—N1'	165.5 (1)	O3—C4—C5—C6	173.7 (1)
C1—C2—N1'—C2'	135.8 (1)	C11—C4—C5—C6	−64.9 (1)
C1—C2—N1'—C5'	−105.2 (1)	C10—C5—C6—C7	−2.3 (2)
C2—N1'—C2'—C2'A	−72.4 (2)	C4—C5—C6—C7	176.4 (1)
C5'—N1'—C2'—C2'A	163.8 (2)	C5—C6—C7—C8	1.4 (2)
C2—N1'—C2'—C3'	163.6 (2)	C6—C7—C8—C9	0.2 (3)
C5'—N1'—C2'—C3'	39.8 (2)	C7—C8—C9—C10	−0.9 (3)
N1'—C2'—C3'—C4'	−21.1 (3)	C6—C5—C10—C9	1.6 (2)
C2'A—C2'—C3'—C4'	−143.4 (2)	C4—C5—C10—C9	−177.0 (1)
C2'—C3'—C4'—C5'	−4.9 (3)	C8—C9—C10—C5	0.0 (3)
C2—N1'—C5'—C4'	−167.7 (2)	O3—C4—C11—C12	−129.2 (1)
C2'—N1'—C5'—C4'	−43.5 (2)	C5—C4—C11—C12	110.4 (1)
C2—N1'—C5'—C5'A	67.6 (2)	O3—C4—C11—C16	50.6 (1)
C2'—N1'—C5'—C5'A	−168.1 (2)	C5—C4—C11—C16	−69.8 (1)
C3'—C4'—C5'—N1'	29.0 (2)	C16—C11—C12—C13	−0.2 (2)
C3'—C4'—C5'—C5'A	152.9 (2)	C4—C11—C12—C13	179.7 (1)
O1—C1—C3—O3	178.07 (9)	C11—C12—C13—C14	−0.2 (3)
C2—C1—C3—O3	−62.3 (1)	C12—C13—C14—C15	0.3 (3)
C1—C3—O3—C4	−165.4 (1)	C13—C14—C15—C16	0.0 (3)
C3—O3—C4—C5	−170.23 (9)	C14—C15—C16—C11	−0.4 (2)
C3—O3—C4—C11	68.1 (1)	C12—C11—C16—C15	0.4 (2)
O3—C4—C5—C10	−7.7 (2)	C4—C11—C16—C15	−179.4 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1′^i	0.98 (2)	1.91 (2)	2.870 (1)	167 (2)
C15—H15···O1^ii	0.95 (2)	2.49 (2)	3.400 (2)	161 (2)

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