Ethyl 4-benzoyl-3,5-diphenyl­pyrrolidine-2-carboxyl­ate

The title compound, C₂₆H₂₅NO₃, was synthesized by the 1,3-dipolar cyclo­addition reaction of benzaldehyde, α-bromo­acetophenone and N-benzylideneglycine ethyl ester. In the mol­ecule, the heterocyclic five-membered ring adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.91(3), Rep   0.906(10) ......       3.00 su-Ra
              N1   -H1A     1.555   1.555

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           26.48
           From the CIF: _reflns_number_total               2237
           Count of symmetry unique reflns         2249
           Completeness (_total/calc)             99.47%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C9     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C16    = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C20    = ...          S

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

   6 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
   1 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

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Ethyl 4-benzoyl-3,5-diphenylpyrrolidine-2-carboxylate

Crystal data

C26H25NO3	Dx = 1.260 Mg m^−3
Mr = 399.47	Melting point: 146 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2c-2n	Cell parameters from 2513 reflections
a = 22.112 (5) Å	θ = 2.5–22.2°
b = 5.7505 (12) Å	µ = 0.08 mm^−1
c = 16.555 (4) Å	T = 294 K
V = 2105.0 (8) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.24 mm
F(000) = 848

Data collection

Bruker SMART CCD area-detector diffractometer	2237 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→23
Tmin = 0.974, Tmax = 0.981	k = −5→7
11174 measured reflections	l = −20→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.1059P] where P = (Fo^2 + 2Fc^2)/3
2237 reflections	(Δ/σ)max < 0.001
276 parameters	Δρmax = 0.11 e Å^−3
2 restraints	Δρmin = −0.16 e Å^−3

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
O1	0.07338 (9)	0.2994 (4)	0.00818 (15)	0.0550 (6)
O2	0.23520 (11)	0.7398 (4)	0.17894 (17)	0.0736 (8)
O3	0.25423 (9)	1.0434 (4)	0.09973 (16)	0.0568 (6)
N1	0.11100 (11)	0.8637 (5)	0.16126 (17)	0.0487 (7)
C1	0.04535 (12)	0.4808 (5)	0.0047 (2)	0.0397 (7)
C2	−0.01629 (12)	0.4839 (5)	−0.03130 (18)	0.0395 (7)
C3	−0.05554 (14)	0.6717 (6)	−0.0230 (2)	0.0491 (8)
H3	−0.0441	0.8007	0.0072	0.059*
C4	−0.11159 (14)	0.6658 (7)	−0.0598 (3)	0.0629 (10)
H4	−0.1380	0.7902	−0.0535	0.075*
C5	−0.12845 (16)	0.4788 (7)	−0.1052 (3)	0.0685 (11)
H5	−0.1662	0.4774	−0.1300	0.082*
C6	−0.09045 (17)	0.2940 (7)	−0.1145 (2)	0.0632 (10)
H6	−0.1022	0.1671	−0.1456	0.076*
C7	−0.03444 (15)	0.2958 (6)	−0.0775 (2)	0.0499 (8)
H7	−0.0087	0.1693	−0.0837	0.060*
C8	0.07356 (12)	0.7066 (5)	0.03357 (19)	0.0373 (7)
H8	0.0620	0.8284	−0.0048	0.045*
C9	0.05425 (13)	0.7915 (5)	0.12072 (19)	0.0425 (7)
H9	0.0294	0.9311	0.1138	0.051*
C10	0.01965 (13)	0.6266 (5)	0.1743 (2)	0.0451 (8)
C11	−0.03602 (14)	0.6900 (6)	0.2060 (2)	0.0583 (9)
H11	−0.0536	0.8301	0.1905	0.070*
C12	−0.06598 (17)	0.5463 (9)	0.2606 (3)	0.0714 (12)
H12	−0.1029	0.5924	0.2823	0.086*
C13	−0.0413 (2)	0.3384 (9)	0.2824 (3)	0.0739 (12)
H13	−0.0615	0.2413	0.3184	0.089*
C14	0.01341 (19)	0.2741 (7)	0.2507 (2)	0.0650 (10)
H14	0.0304	0.1327	0.2657	0.078*
C15	0.04341 (16)	0.4146 (6)	0.1975 (2)	0.0553 (9)
H15	0.0804	0.3667	0.1765	0.066*
C16	0.15594 (12)	0.8945 (5)	0.09739 (19)	0.0407 (7)
H16	0.1500	1.0458	0.0714	0.049*
C17	0.21874 (14)	0.8810 (6)	0.1309 (2)	0.0461 (8)
C18	0.31709 (14)	1.0452 (7)	0.1254 (3)	0.0649 (10)
H18A	0.3390	0.9187	0.0999	0.078*
H18B	0.3196	1.0257	0.1835	0.078*
C19	0.34371 (17)	1.2723 (8)	0.1013 (3)	0.0857 (13)
H19A	0.3405	1.2907	0.0438	0.129*
H19B	0.3855	1.2769	0.1168	0.129*
H19C	0.3223	1.3960	0.1277	0.129*
C20	0.14289 (12)	0.6984 (5)	0.03609 (19)	0.0391 (7)
H20	0.1549	0.5505	0.0607	0.047*
C21	0.17499 (12)	0.7203 (5)	−0.04359 (18)	0.0393 (7)
C22	0.21327 (14)	0.5449 (6)	−0.0687 (2)	0.0516 (9)
H22	0.2183	0.4128	−0.0370	0.062*
C23	0.24464 (15)	0.5654 (7)	−0.1420 (3)	0.0634 (11)
H23	0.2702	0.4464	−0.1588	0.076*
C24	0.23784 (16)	0.7592 (7)	−0.1889 (2)	0.0633 (10)
H24	0.2588	0.7730	−0.2374	0.076*
C25	0.19970 (15)	0.9333 (6)	−0.1639 (2)	0.0552 (9)
H25	0.1949	1.0657	−0.1955	0.066*
C26	0.16878 (14)	0.9128 (6)	−0.0928 (2)	0.0476 (8)
H26	0.1428	1.0317	−0.0771	0.057*
H1A	0.1244 (14)	0.739 (4)	0.190 (2)	0.065 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0561 (13)	0.0356 (12)	0.0734 (18)	0.0083 (10)	−0.0146 (12)	−0.0049 (12)
O2	0.0748 (15)	0.0704 (16)	0.076 (2)	−0.0061 (13)	−0.0322 (15)	0.0195 (16)
O3	0.0443 (12)	0.0694 (15)	0.0565 (15)	−0.0093 (11)	−0.0050 (11)	0.0055 (13)
N1	0.0490 (15)	0.0516 (17)	0.0454 (18)	−0.0051 (14)	−0.0003 (14)	−0.0051 (14)
C1	0.0452 (16)	0.0346 (16)	0.0395 (18)	0.0015 (14)	0.0009 (14)	0.0004 (14)
C2	0.0391 (16)	0.0387 (17)	0.0407 (19)	−0.0057 (14)	−0.0004 (14)	0.0054 (14)
C3	0.0472 (18)	0.0425 (18)	0.058 (2)	0.0008 (15)	−0.0029 (16)	0.0011 (16)
C4	0.0431 (19)	0.060 (2)	0.085 (3)	0.0068 (17)	−0.0088 (19)	0.010 (2)
C5	0.048 (2)	0.074 (3)	0.083 (3)	−0.008 (2)	−0.024 (2)	0.018 (2)
C6	0.061 (2)	0.058 (2)	0.071 (3)	−0.015 (2)	−0.018 (2)	−0.001 (2)
C7	0.0494 (17)	0.0428 (18)	0.057 (2)	−0.0034 (15)	−0.0044 (17)	0.0031 (17)
C8	0.0389 (15)	0.0316 (15)	0.0414 (19)	0.0013 (12)	−0.0037 (13)	0.0005 (13)
C9	0.0430 (16)	0.0384 (17)	0.046 (2)	0.0031 (13)	−0.0004 (14)	−0.0058 (15)
C10	0.0461 (17)	0.0454 (18)	0.044 (2)	−0.0024 (14)	−0.0011 (15)	−0.0076 (16)
C11	0.0478 (19)	0.069 (2)	0.058 (2)	−0.0042 (18)	−0.0004 (18)	−0.006 (2)
C12	0.045 (2)	0.102 (3)	0.066 (3)	−0.019 (2)	0.0105 (19)	−0.017 (3)
C13	0.084 (3)	0.086 (3)	0.052 (3)	−0.032 (3)	0.009 (2)	0.000 (2)
C14	0.088 (3)	0.052 (2)	0.055 (3)	−0.0161 (19)	−0.001 (2)	0.0004 (18)
C15	0.069 (2)	0.0463 (19)	0.050 (2)	−0.0021 (17)	0.0069 (18)	−0.0059 (17)
C16	0.0429 (16)	0.0364 (16)	0.0429 (18)	0.0009 (13)	−0.0060 (15)	0.0019 (15)
C17	0.0515 (18)	0.0464 (19)	0.0404 (19)	−0.0004 (16)	−0.0068 (16)	−0.0036 (16)
C18	0.0393 (17)	0.090 (3)	0.065 (3)	0.0004 (17)	−0.0014 (16)	−0.006 (2)
C19	0.057 (2)	0.103 (3)	0.097 (3)	−0.020 (2)	0.004 (2)	−0.008 (3)
C20	0.0417 (16)	0.0351 (15)	0.0405 (17)	0.0022 (13)	−0.0053 (14)	0.0024 (14)
C21	0.0335 (15)	0.0413 (19)	0.043 (2)	−0.0048 (14)	−0.0056 (13)	−0.0046 (15)
C22	0.0499 (18)	0.0472 (19)	0.058 (2)	0.0030 (15)	−0.0046 (17)	−0.0065 (17)
C23	0.050 (2)	0.071 (2)	0.069 (3)	0.0009 (18)	0.0106 (19)	−0.025 (2)
C24	0.056 (2)	0.083 (3)	0.050 (2)	−0.020 (2)	0.0055 (17)	−0.013 (2)
C25	0.062 (2)	0.058 (2)	0.046 (2)	−0.0113 (19)	−0.0011 (18)	0.0011 (18)
C26	0.0465 (18)	0.048 (2)	0.048 (2)	−0.0023 (15)	−0.0020 (16)	−0.0011 (17)

Geometric parameters (Å, º)

O1—C1	1.214 (3)	C12—C13	1.363 (6)
O2—C17	1.194 (4)	C12—H12	0.9300
O3—C17	1.324 (4)	C13—C14	1.371 (5)
O3—C18	1.453 (4)	C13—H13	0.9300
N1—C16	1.462 (4)	C14—C15	1.368 (5)
N1—C9	1.482 (4)	C14—H14	0.9300
N1—H1A	0.906 (10)	C15—H15	0.9300
C1—C2	1.487 (4)	C16—C17	1.497 (4)
C1—C8	1.518 (4)	C16—C20	1.544 (4)
C2—C7	1.384 (4)	C16—H16	0.9800
C2—C3	1.392 (4)	C18—C19	1.487 (5)
C3—C4	1.381 (5)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700
C4—C5	1.364 (6)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C5—C6	1.364 (5)	C19—H19C	0.9600
C5—H5	0.9300	C20—C21	1.503 (4)
C6—C7	1.381 (5)	C20—H20	0.9800
C6—H6	0.9300	C21—C22	1.381 (4)
C7—H7	0.9300	C21—C26	1.381 (4)
C8—C20	1.534 (4)	C22—C23	1.402 (5)
C8—C9	1.582 (4)	C22—H22	0.9300
C8—H8	0.9800	C23—C24	1.367 (5)
C9—C10	1.507 (4)	C23—H23	0.9300
C9—H9	0.9800	C24—C25	1.373 (5)
C10—C15	1.382 (5)	C24—H24	0.9300
C10—C11	1.386 (4)	C25—C26	1.366 (5)
C11—C12	1.393 (6)	C25—H25	0.9300
C11—H11	0.9300	C26—H26	0.9300
C17—O3—C18	117.2 (3)	C15—C14—H14	119.5
C16—N1—C9	106.4 (2)	C13—C14—H14	119.5
C16—N1—H1A	104 (2)	C14—C15—C10	121.0 (4)
C9—N1—H1A	107 (2)	C14—C15—H15	119.5
O1—C1—C2	119.8 (3)	C10—C15—H15	119.5
O1—C1—C8	120.6 (3)	N1—C16—C17	110.9 (3)
C2—C1—C8	119.5 (3)	N1—C16—C20	105.1 (2)
C7—C2—C3	118.7 (3)	C17—C16—C20	112.2 (2)
C7—C2—C1	118.5 (3)	N1—C16—H16	109.5
C3—C2—C1	122.8 (3)	C17—C16—H16	109.5
C4—C3—C2	119.8 (3)	C20—C16—H16	109.5
C4—C3—H3	120.1	O2—C17—O3	124.0 (3)
C2—C3—H3	120.1	O2—C17—C16	124.4 (3)
C5—C4—C3	120.5 (3)	O3—C17—C16	111.6 (3)
C5—C4—H4	119.7	O3—C18—C19	107.8 (3)
C3—C4—H4	119.7	O3—C18—H18A	110.1
C4—C5—C6	120.5 (3)	C19—C18—H18A	110.1
C4—C5—H5	119.7	O3—C18—H18B	110.1
C6—C5—H5	119.7	C19—C18—H18B	110.1
C5—C6—C7	119.8 (4)	H18A—C18—H18B	108.5
C5—C6—H6	120.1	C18—C19—H19A	109.5
C7—C6—H6	120.1	C18—C19—H19B	109.5
C6—C7—C2	120.7 (3)	H19A—C19—H19B	109.5
C6—C7—H7	119.6	C18—C19—H19C	109.5
C2—C7—H7	119.6	H19A—C19—H19C	109.5
C1—C8—C20	113.1 (2)	H19B—C19—H19C	109.5
C1—C8—C9	116.2 (2)	C21—C20—C8	116.4 (2)
C20—C8—C9	104.7 (2)	C21—C20—C16	115.3 (2)
C1—C8—H8	107.5	C8—C20—C16	100.5 (2)
C20—C8—H8	107.5	C21—C20—H20	108.0
C9—C8—H8	107.5	C8—C20—H20	108.0
N1—C9—C10	109.8 (3)	C16—C20—H20	108.0
N1—C9—C8	105.7 (2)	C22—C21—C26	117.9 (3)
C10—C9—C8	118.7 (2)	C22—C21—C20	119.5 (3)
N1—C9—H9	107.4	C26—C21—C20	122.5 (3)
C10—C9—H9	107.4	C21—C22—C23	120.2 (3)
C8—C9—H9	107.4	C21—C22—H22	119.9
C15—C10—C11	117.7 (3)	C23—C22—H22	119.9
C15—C10—C9	121.7 (3)	C24—C23—C22	120.4 (3)
C11—C10—C9	120.5 (3)	C24—C23—H23	119.8
C10—C11—C12	120.8 (4)	C22—C23—H23	119.8
C10—C11—H11	119.6	C23—C24—C25	119.4 (4)
C12—C11—H11	119.6	C23—C24—H24	120.3
C13—C12—C11	120.2 (4)	C25—C24—H24	120.3
C13—C12—H12	119.9	C26—C25—C24	120.3 (4)
C11—C12—H12	119.9	C26—C25—H25	119.9
C12—C13—C14	119.2 (4)	C24—C25—H25	119.9
C12—C13—H13	120.4	C25—C26—C21	121.8 (3)
C14—C13—H13	120.4	C25—C26—H26	119.1
C15—C14—C13	121.1 (4)	C21—C26—H26	119.1
O1—C1—C2—C7	−15.7 (5)	C11—C10—C15—C14	−1.0 (5)
C8—C1—C2—C7	161.9 (3)	C9—C10—C15—C14	175.3 (3)
O1—C1—C2—C3	166.8 (3)	C9—N1—C16—C17	−159.1 (3)
C8—C1—C2—C3	−15.7 (4)	C9—N1—C16—C20	−37.7 (3)
C7—C2—C3—C4	0.8 (5)	C18—O3—C17—O2	1.0 (5)
C1—C2—C3—C4	178.3 (3)	C18—O3—C17—C16	−178.2 (3)
C2—C3—C4—C5	−1.0 (6)	N1—C16—C17—O2	43.5 (4)
C3—C4—C5—C6	0.5 (6)	C20—C16—C17—O2	−73.6 (4)
C4—C5—C6—C7	0.1 (6)	N1—C16—C17—O3	−137.3 (3)
C5—C6—C7—C2	−0.3 (5)	C20—C16—C17—O3	105.5 (3)
C3—C2—C7—C6	−0.2 (5)	C17—O3—C18—C19	−165.2 (3)
C1—C2—C7—C6	−177.8 (3)	C1—C8—C20—C21	76.9 (3)
O1—C1—C8—C20	21.2 (4)	C9—C8—C20—C21	−155.6 (2)
C2—C1—C8—C20	−156.4 (3)	C1—C8—C20—C16	−157.8 (3)
O1—C1—C8—C9	−100.0 (3)	C9—C8—C20—C16	−30.3 (3)
C2—C1—C8—C9	82.4 (3)	N1—C16—C20—C21	168.3 (2)
C16—N1—C9—C10	146.4 (2)	C17—C16—C20—C21	−71.1 (3)
C16—N1—C9—C8	17.2 (3)	N1—C16—C20—C8	42.2 (3)
C1—C8—C9—N1	135.0 (3)	C17—C16—C20—C8	162.8 (3)
C20—C8—C9—N1	9.4 (3)	C8—C20—C21—C22	−121.5 (3)
C1—C8—C9—C10	11.2 (4)	C16—C20—C21—C22	121.1 (3)
C20—C8—C9—C10	−114.4 (3)	C8—C20—C21—C26	59.8 (4)
N1—C9—C10—C15	−61.8 (4)	C16—C20—C21—C26	−57.6 (4)
C8—C9—C10—C15	59.9 (4)	C26—C21—C22—C23	0.3 (4)
N1—C9—C10—C11	114.4 (3)	C20—C21—C22—C23	−178.5 (3)
C8—C9—C10—C11	−123.9 (3)	C21—C22—C23—C24	0.3 (5)
C15—C10—C11—C12	1.5 (5)	C22—C23—C24—C25	−0.4 (5)
C9—C10—C11—C12	−174.8 (3)	C23—C24—C25—C26	−0.1 (5)
C10—C11—C12—C13	−1.4 (6)	C24—C25—C26—C21	0.7 (5)
C11—C12—C13—C14	0.8 (6)	C22—C21—C26—C25	−0.7 (4)
C12—C13—C14—C15	−0.3 (6)	C20—C21—C26—C25	177.9 (3)
C13—C14—C15—C10	0.5 (6)