Methyl 1-tert-butyl-4-(hydroxy­diphenylmeth­yl)-2-oxopyrrolidine-3-carboxyl­ate

In the title compound, C₂₃H₂₇NO₄, the γ-lactam ring adopts an envelope conformation. An O—H...O hydrogen bond links the mol­ecules into a chain which runs parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.123
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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

   1 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

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD (McArdle, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Methyl 1-tert-butyl-4-(hydroxydiphenylmethyl)-2-oxopyrrolidine-3-carboxylate

Crystal data

C23H27NO4	F(000) = 816
Mr = 381.46	Dx = 1.243 Mg m^−3
Monoclinic, P21/c	Melting point: 422 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.426 (2) Å	Cell parameters from 25 reflections
b = 11.001 (2) Å	θ = 11.7–13.8°
c = 13.933 (4) Å	µ = 0.09 mm^−1
β = 97.85 (1)°	T = 295 K
V = 2038.6 (8) Å^3	Parallelepiped, colourless
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 25.2°, θmin = 1.5°
ω/2θ scans	h = −16→15
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −1→13
Tmin = 0.967, Tmax = 0.975	l = 0→16
4247 measured reflections	3 standard reflections every 60 min
3654 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.1905P] where P = (Fo^2 + 2Fc^2)/3
3654 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. ¹H NMR (400 MHz, CDCl₃, δ): 1.31 (s, 9H), 2.88 (s, 1H), 3.33 (ABd, J_AB = 6.9 Hz, J = 10.0 Hz, 1H), 3.45 (s, 3H), 3.57 (ABd, J_AB = 6.9 Hz, J = 10.0 Hz, 1H), 6.59 (d, J = 7.8 Hz, 1H), 3.88–3.94 (m, 1H), 7.23–7.49 (m, 10H); ¹³C NMR (100 MHz, CDCl₃, δ): 171.2, 169.1, 144.9, 144.8, 128.8, 128.4, 125.8, 125.7, 54.9, 52.4, 52.3, 46.0, 43.2, 27.6.

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
C5	0.39787 (17)	0.1364 (2)	0.82282 (16)	0.0370 (6)
O1	0.46232 (13)	0.25622 (18)	0.65430 (13)	0.0568 (5)
O2	0.68706 (15)	0.24328 (18)	0.55609 (13)	0.0596 (6)
O3	0.62358 (15)	0.05846 (17)	0.57340 (11)	0.0533 (5)
O4	0.77506 (13)	0.23350 (15)	0.87884 (11)	0.0436 (5)
H4	0.7472	0.2309	0.9276	0.065*
C1	0.52047 (19)	0.1969 (2)	0.71149 (17)	0.0380 (6)
C2	0.63303 (17)	0.1889 (2)	0.70748 (15)	0.0340 (6)
H2	0.6641	0.2661	0.7304	0.041*
C3	0.66995 (17)	0.0891 (2)	0.78102 (14)	0.0312 (6)
H3	0.6729	0.0122	0.7460	0.037*
C4	0.58665 (16)	0.0797 (2)	0.84535 (15)	0.0359 (6)
H4A	0.5750	−0.0044	0.8614	0.043*
H4B	0.6042	0.1252	0.9049	0.043*
N1	0.49794 (14)	0.13148 (17)	0.78762 (13)	0.0349 (5)
C6	0.65241 (18)	0.1685 (2)	0.60464 (17)	0.0383 (6)
C7	0.6392 (2)	0.0278 (3)	0.47557 (18)	0.0664 (9)
H7A	0.6024	0.0853	0.4301	0.100*
H7B	0.6148	−0.0548	0.4603	0.100*
H7C	0.7112	0.0322	0.4701	0.100*
C8	0.3160 (2)	0.0961 (3)	0.74190 (18)	0.0572 (8)
H8A	0.3175	0.1483	0.6851	0.086*
H8B	0.2501	0.1025	0.7643	0.086*
H8C	0.3279	0.0115	0.7244	0.086*
C9	0.3967 (2)	0.0505 (3)	0.90838 (18)	0.0516 (8)
H9A	0.4149	−0.0316	0.8897	0.077*
H9B	0.3292	0.0492	0.9277	0.077*
H9C	0.4452	0.0786	0.9628	0.077*
C10	0.3799 (2)	0.2649 (3)	0.8549 (2)	0.0567 (8)
H10A	0.4299	0.2858	0.9105	0.085*
H10B	0.3123	0.2710	0.8736	0.085*
H10C	0.3860	0.3212	0.8015	0.085*
C11	0.77523 (17)	0.1152 (2)	0.83708 (15)	0.0327 (6)
C12	0.85193 (17)	0.1184 (2)	0.76491 (16)	0.0356 (6)
C13	0.90814 (18)	0.2208 (3)	0.75347 (18)	0.0469 (7)
H13	0.8994	0.2921	0.7912	0.056*
C14	0.9776 (2)	0.2222 (3)	0.6876 (2)	0.0599 (8)
H14	1.0152	0.2918	0.6806	0.072*
C15	0.9903 (2)	0.1214 (3)	0.6334 (2)	0.0661 (9)
H15	1.0367	0.1224	0.5896	0.079*
C16	0.9350 (2)	0.0190 (3)	0.6435 (2)	0.0641 (9)
H16	0.9433	−0.0494	0.6062	0.077*
C17	0.8667 (2)	0.0173 (3)	0.70931 (18)	0.0496 (7)
H17	0.8299	−0.0530	0.7164	0.060*
C18	0.80686 (16)	0.0190 (2)	0.91525 (15)	0.0324 (6)
C19	0.86649 (18)	0.0514 (3)	1.00077 (17)	0.0455 (7)
H19	0.8853	0.1322	1.0113	0.055*
C20	0.8983 (2)	−0.0347 (3)	1.07053 (19)	0.0538 (8)
H20	0.9378	−0.0110	1.1276	0.065*
C21	0.87245 (19)	−0.1537 (3)	1.05662 (19)	0.0514 (8)
H21	0.8946	−0.2112	1.1036	0.062*
C22	0.81324 (18)	−0.1883 (3)	0.97243 (18)	0.0456 (7)
H22	0.7954	−0.2695	0.9622	0.055*
C23	0.78040 (18)	−0.1018 (2)	0.90307 (16)	0.0403 (6)
H23	0.7395	−0.1256	0.8469	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C5	0.0394 (15)	0.0436 (16)	0.0290 (12)	0.0084 (12)	0.0091 (11)	0.0040 (12)
O1	0.0567 (11)	0.0721 (14)	0.0427 (11)	0.0220 (11)	0.0110 (9)	0.0302 (10)
O2	0.0913 (14)	0.0558 (13)	0.0374 (10)	−0.0075 (11)	0.0292 (10)	0.0095 (10)
O3	0.0853 (14)	0.0524 (13)	0.0252 (9)	−0.0134 (11)	0.0184 (9)	−0.0040 (9)
O4	0.0595 (12)	0.0415 (11)	0.0315 (10)	−0.0041 (9)	0.0123 (8)	−0.0083 (8)
C1	0.0490 (15)	0.0399 (15)	0.0262 (13)	0.0081 (13)	0.0094 (12)	0.0057 (12)
C2	0.0450 (15)	0.0358 (14)	0.0229 (12)	−0.0016 (12)	0.0103 (11)	0.0020 (11)
C3	0.0381 (13)	0.0330 (14)	0.0237 (11)	0.0015 (12)	0.0083 (10)	0.0012 (11)
C4	0.0371 (14)	0.0458 (15)	0.0256 (12)	0.0015 (12)	0.0072 (11)	0.0059 (12)
N1	0.0375 (11)	0.0423 (13)	0.0264 (10)	0.0095 (10)	0.0098 (9)	0.0092 (10)
C6	0.0451 (15)	0.0435 (17)	0.0274 (13)	0.0033 (13)	0.0097 (12)	0.0071 (13)
C7	0.104 (3)	0.071 (2)	0.0277 (14)	−0.0058 (19)	0.0198 (16)	−0.0118 (14)
C8	0.0509 (17)	0.081 (2)	0.0399 (15)	−0.0026 (17)	0.0071 (13)	−0.0007 (16)
C9	0.0466 (16)	0.067 (2)	0.0455 (15)	0.0090 (15)	0.0197 (13)	0.0213 (15)
C10	0.0618 (18)	0.056 (2)	0.0560 (18)	0.0122 (16)	0.0215 (15)	0.0000 (15)
C11	0.0411 (14)	0.0320 (15)	0.0266 (12)	−0.0002 (12)	0.0101 (10)	−0.0042 (11)
C12	0.0344 (13)	0.0442 (16)	0.0281 (12)	−0.0014 (12)	0.0048 (10)	0.0045 (12)
C13	0.0480 (16)	0.0528 (19)	0.0409 (15)	−0.0047 (14)	0.0095 (13)	0.0021 (13)
C14	0.0559 (18)	0.067 (2)	0.060 (2)	−0.0141 (16)	0.0211 (16)	0.0114 (17)
C15	0.062 (2)	0.089 (3)	0.0543 (18)	−0.0014 (19)	0.0342 (16)	0.0076 (19)
C16	0.075 (2)	0.072 (2)	0.0531 (18)	0.0013 (19)	0.0357 (17)	−0.0099 (17)
C17	0.0564 (18)	0.0513 (18)	0.0453 (15)	−0.0043 (14)	0.0219 (14)	−0.0037 (14)
C18	0.0305 (13)	0.0437 (16)	0.0244 (12)	0.0009 (12)	0.0088 (10)	−0.0015 (11)
C19	0.0438 (15)	0.0564 (18)	0.0351 (14)	−0.0077 (14)	0.0013 (12)	−0.0016 (13)
C20	0.0457 (16)	0.080 (2)	0.0327 (15)	−0.0014 (16)	−0.0039 (13)	0.0043 (16)
C21	0.0456 (16)	0.067 (2)	0.0409 (16)	0.0118 (16)	0.0053 (13)	0.0161 (16)
C22	0.0481 (16)	0.0479 (17)	0.0416 (16)	0.0065 (14)	0.0088 (13)	0.0035 (14)
C23	0.0441 (15)	0.0497 (19)	0.0261 (13)	0.0047 (13)	0.0016 (11)	0.0007 (13)

Geometric parameters (Å, º)

C5—N1	1.493 (3)	C9—H9C	0.9801
C5—C10	1.512 (3)	C10—H10A	0.9801
C5—C9	1.523 (3)	C10—H10B	0.9801
C5—C8	1.529 (3)	C10—H10C	0.9801
O1—C1	1.225 (3)	C11—C12	1.535 (3)
O2—C6	1.198 (3)	C11—C18	1.536 (3)
O3—C6	1.327 (3)	C12—C13	1.377 (3)
O3—C7	1.447 (3)	C12—C17	1.385 (3)
O4—C11	1.426 (3)	C13—C14	1.395 (3)
O4—H4	0.8200	C13—H13	0.9600
C1—N1	1.350 (3)	C14—C15	1.364 (4)
C1—C2	1.522 (3)	C14—H14	0.9300
C2—C6	1.508 (3)	C15—C16	1.367 (4)
C2—C3	1.537 (3)	C15—H15	0.9300
C2—H2	0.9800	C16—C17	1.383 (3)
C3—C4	1.529 (3)	C16—H16	0.9300
C3—C11	1.546 (3)	C17—H17	0.9300
C3—H3	0.9800	C18—C23	1.380 (3)
C4—N1	1.459 (3)	C18—C19	1.388 (3)
C4—H4A	0.9700	C19—C20	1.382 (4)
C4—H4B	0.9700	C19—H19	0.9300
C7—H7A	0.9801	C20—C21	1.362 (4)
C7—H7B	0.9801	C20—H20	0.9300
C7—H7C	0.9801	C21—C22	1.378 (4)
C8—H8A	0.9801	C21—H21	0.9300
C8—H8B	0.9801	C22—C23	1.385 (3)
C8—H8C	0.9801	C22—H22	0.9300
C9—H9A	0.9801	C23—H23	0.9300
C9—H9B	0.9801
N1—C5—C10	108.5 (2)	H9A—C9—H9C	109.5
N1—C5—C9	109.93 (19)	H9B—C9—H9C	109.5
C10—C5—C9	109.2 (2)	C5—C10—H10A	109.5
N1—C5—C8	109.63 (18)	C5—C10—H10B	109.5
C10—C5—C8	111.2 (2)	H10A—C10—H10B	109.5
C9—C5—C8	108.3 (2)	C5—C10—H10C	109.5
C6—O3—C7	116.6 (2)	H10A—C10—H10C	109.5
C11—O4—H4	109.5	H10B—C10—H10C	109.5
O1—C1—N1	127.1 (2)	O4—C11—C12	106.53 (18)
O1—C1—C2	123.7 (2)	O4—C11—C18	110.80 (18)
N1—C1—C2	109.1 (2)	C12—C11—C18	109.59 (18)
C6—C2—C1	110.15 (19)	O4—C11—C3	108.88 (18)
C6—C2—C3	116.5 (2)	C12—C11—C3	108.80 (17)
C1—C2—C3	104.39 (18)	C18—C11—C3	112.06 (18)
C6—C2—H2	108.5	C13—C12—C17	118.0 (2)
C1—C2—H2	108.5	C13—C12—C11	121.5 (2)
C3—C2—H2	108.5	C17—C12—C11	120.5 (2)
C4—C3—C2	104.13 (17)	C12—C13—C14	120.7 (3)
C4—C3—C11	114.07 (17)	C12—C13—H13	119.6
C2—C3—C11	113.19 (18)	C14—C13—H13	119.6
C4—C3—H3	108.4	C15—C14—C13	120.1 (3)
C2—C3—H3	108.4	C15—C14—H14	120.0
C11—C3—H3	108.4	C13—C14—H14	120.0
N1—C4—C3	104.93 (16)	C14—C15—C16	120.1 (3)
N1—C4—H4A	110.8	C14—C15—H15	119.9
C3—C4—H4A	110.8	C16—C15—H15	119.9
N1—C4—H4B	110.8	C15—C16—C17	119.8 (3)
C3—C4—H4B	110.8	C15—C16—H16	120.1
H4A—C4—H4B	108.8	C17—C16—H16	120.1
C1—N1—C4	112.82 (19)	C16—C17—C12	121.2 (3)
C1—N1—C5	123.18 (19)	C16—C17—H17	119.4
C4—N1—C5	122.44 (17)	C12—C17—H17	119.4
O2—C6—O3	124.0 (2)	C23—C18—C19	117.5 (2)
O2—C6—C2	124.4 (2)	C23—C18—C11	122.3 (2)
O3—C6—C2	111.5 (2)	C19—C18—C11	120.2 (2)
O3—C7—H7A	109.5	C20—C19—C18	120.9 (3)
O3—C7—H7B	109.5	C20—C19—H19	119.5
H7A—C7—H7B	109.5	C18—C19—H19	119.5
O3—C7—H7C	109.5	C21—C20—C19	120.7 (3)
H7A—C7—H7C	109.5	C21—C20—H20	119.7
H7B—C7—H7C	109.5	C19—C20—H20	119.7
C5—C8—H8A	109.5	C20—C21—C22	119.6 (3)
C5—C8—H8B	109.5	C20—C21—H21	120.2
H8A—C8—H8B	109.5	C22—C21—H21	120.2
C5—C8—H8C	109.5	C21—C22—C23	119.7 (3)
H8A—C8—H8C	109.5	C21—C22—H22	120.2
H8B—C8—H8C	109.5	C23—C22—H22	120.2
C5—C9—H9A	109.5	C18—C23—C22	121.6 (2)
C5—C9—H9B	109.5	C18—C23—H23	119.2
H9A—C9—H9B	109.5	C22—C23—H23	119.2
C5—C9—H9C	109.5
O1—C1—C2—C6	−44.9 (3)	C2—C3—C11—C12	−62.9 (2)
N1—C1—C2—C6	136.3 (2)	C4—C3—C11—C18	56.9 (3)
O1—C1—C2—C3	−170.7 (2)	C2—C3—C11—C18	175.74 (17)
N1—C1—C2—C3	10.5 (2)	O4—C11—C12—C13	2.7 (3)
C6—C2—C3—C4	−140.9 (2)	C18—C11—C12—C13	−117.2 (2)
C1—C2—C3—C4	−19.2 (2)	C3—C11—C12—C13	119.9 (2)
C6—C2—C3—C11	94.7 (2)	O4—C11—C12—C17	−177.5 (2)
C1—C2—C3—C11	−143.60 (19)	C18—C11—C12—C17	62.6 (3)
C2—C3—C4—N1	21.1 (2)	C3—C11—C12—C17	−60.2 (3)
C11—C3—C4—N1	144.96 (19)	C17—C12—C13—C14	0.1 (4)
O1—C1—N1—C4	−175.4 (3)	C11—C12—C13—C14	179.9 (2)
C2—C1—N1—C4	3.3 (3)	C12—C13—C14—C15	0.1 (4)
O1—C1—N1—C5	−9.4 (4)	C13—C14—C15—C16	0.1 (5)
C2—C1—N1—C5	169.4 (2)	C14—C15—C16—C17	−0.5 (5)
C3—C4—N1—C1	−15.8 (3)	C15—C16—C17—C12	0.8 (5)
C3—C4—N1—C5	178.0 (2)	C13—C12—C17—C16	−0.6 (4)
C10—C5—N1—C1	−61.5 (3)	C11—C12—C17—C16	179.6 (3)
C9—C5—N1—C1	179.0 (2)	O4—C11—C18—C23	156.5 (2)
C8—C5—N1—C1	60.1 (3)	C12—C11—C18—C23	−86.2 (3)
C10—C5—N1—C4	103.2 (2)	C3—C11—C18—C23	34.7 (3)
C9—C5—N1—C4	−16.2 (3)	O4—C11—C18—C19	−25.3 (3)
C8—C5—N1—C4	−135.2 (2)	C12—C11—C18—C19	92.0 (2)
C7—O3—C6—O2	2.3 (4)	C3—C11—C18—C19	−147.2 (2)
C7—O3—C6—C2	−179.5 (2)	C23—C18—C19—C20	0.3 (4)
C1—C2—C6—O2	108.8 (3)	C11—C18—C19—C20	−177.9 (2)
C3—C2—C6—O2	−132.6 (3)	C18—C19—C20—C21	0.5 (4)
C1—C2—C6—O3	−69.4 (3)	C19—C20—C21—C22	−0.6 (4)
C3—C2—C6—O3	49.2 (3)	C20—C21—C22—C23	−0.2 (4)
C4—C3—C11—O4	−66.0 (2)	C19—C18—C23—C22	−1.1 (3)
C2—C3—C11—O4	52.8 (2)	C11—C18—C23—C22	177.1 (2)
C4—C3—C11—C12	178.3 (2)	C21—C22—C23—C18	1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^i	0.82	2.08	2.891 (2)	169

Symmetry code: (i) x, −y+1/2, z+1/2.