1-Benzoyl-6-ethyl-5-(phenyl­sulfon­yl)perhydro­pyrrolo[3,4-b]pyrrole

In the title compound, C₂₁H₂₆N₂O₂S, one of the pyrrolidine rings adopts a twist conformation, while the other is in an envelope conformation. Weak C—H...O inter­actions stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.127
• Data-to-parameter ratio = 31.4

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.520
           From the CIF: _refine_ls_abs_structure_Flack_su    0.060
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.52
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.09
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.093
            Tmax scaled      0.965 Tmin scaled      0.878
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           32.70
           From the CIF: _reflns_number_total               7377
           Count of symmetry unique reflns         4165
           Completeness (_total/calc)            177.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3212
           Fraction of Friedel pairs measured     0.771
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

1-Benzoyl-6-ethyl-5-(phenylsulfonyl)perhydropyrrolo[3,4-b]pyrrole

Crystal data

C21H26N2O2S	F(000) = 792
Mr = 370.50	Dx = 1.224 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 39402 reflections
a = 8.1022 (2) Å	θ = 2.1–32.7°
b = 9.9925 (2) Å	µ = 0.18 mm^−1
c = 24.8288 (5) Å	T = 293 K
V = 2010.17 (8) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa-APEXII area-detector diffractometer	7377 independent reflections
Radiation source: fine-focus sealed tube	5770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 32.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	h = −11→12
Tmin = 0.803, Tmax = 0.883	k = −15→10
39402 measured reflections	l = −37→28

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.1323P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7377 reflections	Δρmax = 0.37 e Å^−3
235 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 3223 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.52 (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
S1	0.60207 (5)	0.53847 (4)	0.239943 (13)	0.04630 (10)
N1	0.68186 (15)	0.64223 (12)	0.07120 (4)	0.0398 (2)
N2	0.57674 (15)	0.65159 (12)	0.19410 (4)	0.0411 (2)
C6	0.47453 (18)	0.62178 (16)	0.14603 (5)	0.0424 (3)
H6	0.4850	0.5271	0.1363	0.051*
C15	0.7386 (2)	0.41615 (15)	0.21463 (5)	0.0442 (3)
O2	0.6826 (2)	0.60255 (15)	0.28424 (4)	0.0679 (4)
C5	0.7138 (2)	0.74275 (15)	0.18131 (6)	0.0458 (3)
H5A	0.8140	0.6934	0.1733	0.055*
H5B	0.7351	0.8039	0.2108	0.055*
C7	0.55312 (19)	0.70939 (14)	0.10248 (6)	0.0416 (3)
H7	0.4693	0.7492	0.0790	0.050*
C9	0.75508 (19)	0.47437 (14)	0.00291 (5)	0.0436 (3)
C8	0.61827 (19)	0.55120 (17)	0.03029 (6)	0.0497 (3)
H8A	0.5576	0.6020	0.0035	0.060*
H8B	0.5423	0.4886	0.0469	0.060*
C4	0.6515 (2)	0.81669 (14)	0.13217 (6)	0.0483 (3)
H4	0.5820	0.8930	0.1421	0.058*
C10	0.7620 (2)	0.46460 (19)	−0.05280 (6)	0.0563 (4)
H10	0.6836	0.5086	−0.0737	0.068*
C16	0.6750 (3)	0.30066 (17)	0.19180 (7)	0.0568 (4)
H16	0.5615	0.2878	0.1898	0.068*
O1	0.44579 (17)	0.47526 (13)	0.24773 (5)	0.0657 (4)
C14	0.8746 (2)	0.40921 (19)	0.03273 (7)	0.0591 (4)
H14	0.8722	0.4140	0.0701	0.071*
C2	0.7806 (2)	0.75049 (17)	0.04844 (7)	0.0546 (4)
H2A	0.7293	0.7856	0.0161	0.066*
H2B	0.8906	0.7192	0.0395	0.066*
C20	0.9080 (2)	0.43559 (18)	0.21798 (7)	0.0571 (4)
H20	0.9500	0.5129	0.2337	0.069*
C3	0.7879 (3)	0.85758 (16)	0.09232 (7)	0.0625 (5)
H3A	0.7664	0.9456	0.0775	0.075*
H3B	0.8950	0.8582	0.1098	0.075*
C17	0.7819 (3)	0.2049 (2)	0.17213 (9)	0.0730 (6)
H17	0.7403	0.1269	0.1569	0.088*
C11	0.8841 (3)	0.3902 (2)	−0.07765 (7)	0.0715 (6)
H11	0.8863	0.3833	−0.1150	0.086*
C21	0.2932 (2)	0.6567 (3)	0.15614 (8)	0.0721 (6)
H21A	0.2585	0.6184	0.1902	0.086*
H21B	0.2814	0.7531	0.1586	0.086*
C19	1.0130 (3)	0.3399 (2)	0.19801 (9)	0.0700 (5)
H19	1.1266	0.3526	0.1999	0.084*
C12	1.0012 (3)	0.3271 (2)	−0.04763 (10)	0.0761 (6)
H12	1.0833	0.2773	−0.0645	0.091*
C18	0.9500 (3)	0.2243 (2)	0.17500 (10)	0.0749 (6)
H18	1.0214	0.1597	0.1615	0.090*
C13	0.9980 (3)	0.3368 (2)	0.00740 (10)	0.0765 (6)
H13	1.0789	0.2946	0.0278	0.092*
C22	0.1843 (3)	0.6047 (4)	0.11195 (9)	0.1066 (11)
H22A	0.0718	0.6287	0.1193	0.160*
H22C	0.1937	0.5090	0.1101	0.160*
H22B	0.2177	0.6431	0.0782	0.160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0541 (2)	0.05103 (18)	0.03378 (14)	0.00048 (16)	0.00773 (14)	0.00629 (13)
N1	0.0415 (6)	0.0426 (5)	0.0354 (5)	0.0023 (5)	0.0081 (4)	−0.0001 (4)
N2	0.0445 (6)	0.0435 (5)	0.0354 (5)	−0.0004 (5)	0.0073 (4)	0.0040 (4)
C6	0.0395 (6)	0.0503 (7)	0.0375 (6)	−0.0001 (6)	0.0050 (5)	0.0061 (5)
C15	0.0490 (7)	0.0459 (7)	0.0378 (6)	0.0016 (6)	−0.0004 (6)	0.0077 (5)
O2	0.0914 (10)	0.0769 (8)	0.0355 (5)	0.0043 (8)	−0.0015 (6)	−0.0061 (6)
C5	0.0505 (8)	0.0426 (7)	0.0442 (7)	−0.0051 (6)	0.0081 (6)	−0.0044 (5)
C7	0.0431 (7)	0.0432 (6)	0.0385 (6)	0.0083 (5)	0.0086 (5)	0.0070 (5)
C9	0.0496 (8)	0.0435 (7)	0.0376 (6)	0.0005 (7)	0.0009 (5)	−0.0037 (5)
C8	0.0450 (7)	0.0609 (9)	0.0432 (7)	0.0052 (7)	−0.0033 (6)	−0.0076 (6)
C4	0.0626 (9)	0.0337 (6)	0.0486 (7)	0.0038 (6)	0.0173 (7)	0.0014 (5)
C10	0.0693 (10)	0.0610 (9)	0.0386 (6)	0.0030 (9)	−0.0013 (7)	−0.0028 (7)
C16	0.0639 (10)	0.0485 (8)	0.0580 (9)	−0.0034 (8)	−0.0045 (8)	0.0009 (7)
O1	0.0609 (7)	0.0662 (7)	0.0700 (8)	−0.0040 (6)	0.0234 (6)	0.0215 (7)
C14	0.0675 (11)	0.0655 (9)	0.0442 (7)	0.0177 (9)	−0.0028 (7)	−0.0027 (7)
C2	0.0638 (10)	0.0541 (8)	0.0459 (8)	−0.0042 (7)	0.0191 (7)	0.0071 (6)
C20	0.0533 (9)	0.0590 (9)	0.0590 (9)	0.0004 (8)	−0.0083 (8)	0.0065 (7)
C3	0.0859 (13)	0.0420 (7)	0.0595 (9)	−0.0136 (8)	0.0264 (9)	0.0029 (7)
C17	0.0952 (16)	0.0508 (9)	0.0729 (12)	0.0095 (10)	−0.0062 (12)	−0.0066 (9)
C11	0.0980 (16)	0.0702 (11)	0.0461 (8)	−0.0022 (12)	0.0209 (10)	−0.0089 (8)
C21	0.0436 (8)	0.1165 (18)	0.0560 (10)	0.0094 (10)	0.0112 (7)	0.0177 (11)
C19	0.0545 (10)	0.0850 (14)	0.0705 (12)	0.0177 (10)	−0.0042 (9)	0.0164 (11)
C12	0.0854 (15)	0.0693 (12)	0.0738 (13)	0.0170 (11)	0.0263 (11)	−0.0108 (10)
C18	0.0863 (14)	0.0696 (12)	0.0688 (12)	0.0320 (11)	0.0003 (11)	0.0059 (10)
C13	0.0772 (14)	0.0757 (13)	0.0765 (13)	0.0323 (11)	−0.0008 (11)	−0.0011 (11)
C22	0.0518 (11)	0.197 (3)	0.0704 (14)	−0.0146 (17)	−0.0061 (10)	0.0233 (18)

Geometric parameters (Å, º)

S1—O1	1.4282 (14)	C16—C17	1.380 (3)
S1—O2	1.4301 (13)	C16—H16	0.93
S1—N2	1.6172 (12)	C14—C13	1.385 (3)
S1—C15	1.7645 (16)	C14—H14	0.93
N1—C8	1.4576 (18)	C2—C3	1.528 (2)
N1—C2	1.4595 (19)	C2—H2A	0.97
N1—C7	1.4634 (17)	C2—H2B	0.97
N2—C5	1.4713 (19)	C20—C19	1.373 (3)
N2—C6	1.4829 (19)	C20—H20	0.93
C6—C7	1.5299 (19)	C3—H3A	0.97
C6—C21	1.531 (2)	C3—H3B	0.97
C6—H6	0.98	C17—C18	1.378 (4)
C15—C16	1.385 (2)	C17—H17	0.93
C15—C20	1.389 (2)	C11—C12	1.361 (3)
C5—C4	1.513 (2)	C11—H11	0.93
C5—H5A	0.97	C21—C22	1.501 (3)
C5—H5B	0.97	C21—H21A	0.97
C7—C4	1.526 (2)	C21—H21B	0.97
C7—H7	0.98	C19—C18	1.386 (3)
C9—C14	1.382 (2)	C19—H19	0.93
C9—C10	1.3878 (19)	C12—C13	1.370 (3)
C9—C8	1.510 (2)	C12—H12	0.93
C8—H8A	0.97	C18—H18	0.93
C8—H8B	0.97	C13—H13	0.93
C4—C3	1.538 (2)	C22—H22A	0.96
C4—H4	0.98	C22—H22C	0.96
C10—C11	1.383 (3)	C22—H22B	0.96
C10—H10	0.93
O1—S1—O2	119.88 (9)	C17—C16—C15	119.28 (19)
O1—S1—N2	106.97 (7)	C17—C16—H16	120.4
O2—S1—N2	106.64 (7)	C15—C16—H16	120.4
O1—S1—C15	107.33 (8)	C9—C14—C13	120.58 (16)
O2—S1—C15	107.35 (8)	C9—C14—H14	119.7
N2—S1—C15	108.24 (6)	C13—C14—H14	119.7
C8—N1—C2	112.74 (12)	N1—C2—C3	105.31 (12)
C8—N1—C7	113.83 (12)	N1—C2—H2A	110.7
C2—N1—C7	104.86 (11)	C3—C2—H2A	110.7
C5—N2—C6	111.86 (11)	N1—C2—H2B	110.7
C5—N2—S1	119.26 (10)	C3—C2—H2B	110.7
C6—N2—S1	119.80 (10)	H2A—C2—H2B	108.8
N2—C6—C7	102.79 (11)	C19—C20—C15	119.58 (18)
N2—C6—C21	110.99 (13)	C19—C20—H20	120.2
C7—C6—C21	112.65 (14)	C15—C20—H20	120.2
N2—C6—H6	110.1	C2—C3—C4	104.18 (13)
C7—C6—H6	110.1	C2—C3—H3A	110.9
C21—C6—H6	110.1	C4—C3—H3A	110.9
C16—C15—C20	120.59 (16)	C2—C3—H3B	110.9
C16—C15—S1	119.31 (13)	C4—C3—H3B	110.9
C20—C15—S1	120.10 (13)	H3A—C3—H3B	108.9
N2—C5—C4	102.96 (13)	C18—C17—C16	120.3 (2)
N2—C5—H5A	111.2	C18—C17—H17	119.9
C4—C5—H5A	111.2	C16—C17—H17	119.9
N2—C5—H5B	111.2	C12—C11—C10	120.21 (17)
C4—C5—H5B	111.2	C12—C11—H11	119.9
H5A—C5—H5B	109.1	C10—C11—H11	119.9
N1—C7—C4	101.90 (12)	C22—C21—C6	111.44 (19)
N1—C7—C6	114.16 (11)	C22—C21—H21A	109.3
C4—C7—C6	106.15 (12)	C6—C21—H21A	109.3
N1—C7—H7	111.4	C22—C21—H21B	109.3
C4—C7—H7	111.4	C6—C21—H21B	109.3
C6—C7—H7	111.4	H21A—C21—H21B	108.0
C14—C9—C10	118.19 (15)	C20—C19—C18	120.1 (2)
C14—C9—C8	120.85 (13)	C20—C19—H19	120.0
C10—C9—C8	120.95 (14)	C18—C19—H19	120.0
N1—C8—C9	111.81 (12)	C11—C12—C13	120.01 (19)
N1—C8—H8A	109.3	C11—C12—H12	120.0
C9—C8—H8A	109.3	C13—C12—H12	120.0
N1—C8—H8B	109.3	C17—C18—C19	120.2 (2)
C9—C8—H8B	109.3	C17—C18—H18	119.9
H8A—C8—H8B	107.9	C19—C18—H18	119.9
C5—C4—C7	102.76 (11)	C12—C13—C14	120.2 (2)
C5—C4—C3	114.12 (15)	C12—C13—H13	119.9
C7—C4—C3	104.54 (12)	C14—C13—H13	119.9
C5—C4—H4	111.6	C21—C22—H22A	109.5
C7—C4—H4	111.6	C21—C22—H22C	109.5
C3—C4—H4	111.6	H22A—C22—H22C	109.5
C11—C10—C9	120.77 (17)	C21—C22—H22B	109.5
C11—C10—H10	119.6	H22A—C22—H22B	109.5
C9—C10—H10	119.6	H22C—C22—H22B	109.5
O1—S1—N2—C5	173.97 (11)	N2—C5—C4—C7	−35.39 (14)
O2—S1—N2—C5	44.57 (13)	N2—C5—C4—C3	−147.94 (12)
C15—S1—N2—C5	−70.66 (12)	N1—C7—C4—C5	−85.23 (12)
O1—S1—N2—C6	−41.66 (12)	C6—C7—C4—C5	34.54 (15)
O2—S1—N2—C6	−171.07 (11)	N1—C7—C4—C3	34.21 (15)
C15—S1—N2—C6	73.71 (12)	C6—C7—C4—C3	153.98 (13)
C5—N2—C6—C7	−3.42 (15)	C14—C9—C10—C11	0.8 (3)
S1—N2—C6—C7	−150.22 (10)	C8—C9—C10—C11	−177.68 (17)
C5—N2—C6—C21	−124.09 (16)	C20—C15—C16—C17	−0.3 (3)
S1—N2—C6—C21	89.12 (16)	S1—C15—C16—C17	−179.84 (15)
O1—S1—C15—C16	18.63 (14)	C10—C9—C14—C13	0.3 (3)
O2—S1—C15—C16	148.74 (13)	C8—C9—C14—C13	178.77 (19)
N2—S1—C15—C16	−96.50 (13)	C8—N1—C2—C3	161.85 (14)
O1—S1—C15—C20	−160.95 (13)	C7—N1—C2—C3	37.48 (18)
O2—S1—C15—C20	−30.84 (15)	C16—C15—C20—C19	0.6 (3)
N2—S1—C15—C20	83.92 (14)	S1—C15—C20—C19	−179.81 (14)
C6—N2—C5—C4	24.83 (15)	N1—C2—C3—C4	−14.73 (19)
S1—N2—C5—C4	171.83 (9)	C5—C4—C3—C2	99.48 (17)
C8—N1—C7—C4	−168.30 (12)	C7—C4—C3—C2	−12.00 (18)
C2—N1—C7—C4	−44.63 (14)	C15—C16—C17—C18	−0.3 (3)
C8—N1—C7—C6	77.75 (16)	C9—C10—C11—C12	−1.1 (3)
C2—N1—C7—C6	−158.58 (13)	N2—C6—C21—C22	−169.8 (2)
N2—C6—C7—N1	91.97 (14)	C7—C6—C21—C22	75.5 (3)
C21—C6—C7—N1	−148.51 (16)	C15—C20—C19—C18	−0.4 (3)
N2—C6—C7—C4	−19.45 (14)	C10—C11—C12—C13	0.2 (4)
C21—C6—C7—C4	100.08 (16)	C16—C17—C18—C19	0.4 (4)
C2—N1—C8—C9	66.34 (17)	C20—C19—C18—C17	−0.1 (3)
C7—N1—C8—C9	−174.38 (12)	C11—C12—C13—C14	0.9 (4)
C14—C9—C8—N1	49.5 (2)	C9—C14—C13—C12	−1.1 (4)
C10—C9—C8—N1	−132.03 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O1^i	0.97	2.48	3.190 (2)	130
C11—H11···O2^ii	0.93	2.57	3.472 (2)	164
C21—H21A···O1	0.97	2.53	3.160 (3)	123

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2.