(3aR,6S,6aR)-6-Benzyl-1-(4-bromo­phen­yl)-5-tosyl-cis-perhydro­pyrrolo[3,4-b]pyrrole

The title compound, C₂₆H₂₇BrN₂O₂S, has two fused pyrrolidine rings, each in a twist conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.048
• wR factor = 0.153
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Br1    -   C10     ..       5.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       5.10 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

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           27.99
           From the CIF: _reflns_number_total               5499
           Count of symmetry unique reflns         3312
           Completeness (_total/calc)            166.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2187
           Fraction of Friedel pairs measured     0.660
           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 C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

(3aR,6S,6aR)-6-Benzyl-1-(4-bromophenyl)-5-tosyl-cis- perhydropyrrolo[3,4-b]pyrrole

Crystal data

C26H27BrN2O2S	F(000) = 1056
Mr = 511.47	Dx = 1.392 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5499 reflections
a = 20.9376 (11) Å	θ = 2.0–28.0°
b = 10.5821 (6) Å	µ = 1.80 mm^−1
c = 11.0154 (6) Å	T = 293 K
V = 2440.6 (2) Å^3	Block, pink
Z = 4	0.24 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3825 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 28.0°, θmin = 2.0°
ω scans	h = −26→25
20524 measured reflections	k = −13→13
5499 independent reflections	l = −14→14

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0922P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.015
5499 reflections	Δρmax = 0.80 e Å^−3
289 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2297 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.031 (13)

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
Br1	0.75538 (4)	0.82111 (7)	1.17057 (5)	0.1300 (3)
S1	0.57403 (4)	0.54068 (8)	0.53884 (8)	0.0553 (2)
C14	0.79794 (14)	0.6280 (3)	0.5415 (3)	0.0505 (7)
C4	0.68041 (13)	0.6773 (3)	0.5432 (3)	0.0494 (7)
H4	0.6803	0.6413	0.6252	0.059*
C13	0.73591 (14)	0.6222 (3)	0.4707 (3)	0.0552 (7)
H13A	0.7265	0.5349	0.4504	0.066*
H13B	0.7407	0.6688	0.3955	0.066*
O1	0.51641 (11)	0.5418 (3)	0.4697 (3)	0.0734 (7)
N2	0.65003 (14)	0.8727 (3)	0.6608 (4)	0.0717 (9)
C3	0.68214 (15)	0.8224 (3)	0.5513 (4)	0.0607 (8)
H3	0.7257	0.8551	0.5434	0.073*
C19	0.80837 (16)	0.5432 (4)	0.6347 (3)	0.0604 (8)
H19	0.7783	0.4807	0.6505	0.073*
C25	0.50878 (15)	0.6728 (3)	0.7116 (3)	0.0568 (8)
H25	0.4840	0.7040	0.6483	0.068*
C22	0.5806 (2)	0.5802 (4)	0.8994 (4)	0.0707 (10)
H22	0.6048	0.5488	0.9633	0.085*
C20	0.55556 (14)	0.5858 (3)	0.6887 (3)	0.0533 (8)
N1	0.61926 (12)	0.6507 (3)	0.4835 (3)	0.0539 (6)
C21	0.59194 (16)	0.5371 (4)	0.7839 (4)	0.0626 (9)
H21	0.6233	0.4766	0.7694	0.075*
O2	0.61163 (11)	0.4295 (2)	0.5452 (3)	0.0667 (7)
C11	0.7553 (2)	0.7845 (4)	0.9143 (4)	0.0756 (11)
H11	0.7932	0.7406	0.9276	0.091*
C7	0.67395 (19)	0.8620 (4)	0.7745 (4)	0.0681 (10)
C12	0.73077 (18)	0.7980 (4)	0.7982 (4)	0.0665 (10)
H12	0.7531	0.7630	0.7334	0.080*
C23	0.53404 (18)	0.6690 (4)	0.9229 (3)	0.0630 (9)
C10	0.7219 (3)	0.8382 (5)	1.0101 (4)	0.0827 (13)
C2	0.63917 (18)	0.8690 (4)	0.4488 (4)	0.0754 (11)
H2	0.6635	0.8826	0.3739	0.091*
C15	0.84330 (16)	0.7203 (4)	0.5205 (4)	0.0642 (9)
H15	0.8373	0.7778	0.4577	0.077*
C24	0.49855 (17)	0.7137 (3)	0.8279 (4)	0.0633 (9)
H24	0.4668	0.7731	0.8427	0.076*
C26	0.5224 (2)	0.7165 (4)	1.0522 (4)	0.0867 (13)
H26A	0.4773	0.7236	1.0664	0.130*
H26B	0.5421	0.7978	1.0623	0.130*
H26C	0.5405	0.6580	1.1092	0.130*
C18	0.8633 (2)	0.5503 (5)	0.7054 (4)	0.0795 (12)
H18	0.8704	0.4912	0.7664	0.095*
C1	0.58973 (18)	0.7668 (4)	0.4326 (4)	0.0728 (10)
H1A	0.5508	0.7878	0.4760	0.087*
H1B	0.5796	0.7554	0.3474	0.087*
C9	0.6669 (3)	0.9047 (5)	0.9909 (5)	0.0971 (17)
H9	0.6456	0.9421	1.0557	0.117*
C8	0.6435 (2)	0.9155 (4)	0.8765 (5)	0.0862 (15)
H8	0.6058	0.9602	0.8649	0.103*
C16	0.89730 (18)	0.7280 (5)	0.5915 (5)	0.0827 (13)
H16	0.9275	0.7904	0.5760	0.099*
C5	0.6119 (2)	0.9922 (4)	0.4971 (6)	0.0924 (17)
H5A	0.6414	1.0616	0.4835	0.111*
H5B	0.5715	1.0118	0.4584	0.111*
C6	0.6031 (2)	0.9684 (4)	0.6294 (6)	0.0900 (15)
H6A	0.6104	1.0451	0.6756	0.108*
H6B	0.5603	0.9383	0.6458	0.108*
C17	0.9069 (2)	0.6440 (7)	0.6852 (4)	0.0962 (17)
H17	0.9428	0.6510	0.7344	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.2020 (7)	0.1285 (5)	0.0594 (3)	−0.0609 (5)	0.0244 (3)	−0.0152 (3)
S1	0.0482 (4)	0.0588 (5)	0.0588 (5)	−0.0019 (4)	−0.0006 (4)	−0.0057 (4)
C14	0.0462 (15)	0.0574 (18)	0.0478 (16)	0.0073 (13)	0.0092 (13)	−0.0030 (15)
C4	0.0445 (14)	0.0548 (16)	0.0488 (16)	0.0036 (13)	0.0045 (13)	−0.0008 (15)
C13	0.0517 (16)	0.0679 (19)	0.0461 (16)	0.0080 (15)	0.0029 (14)	−0.0012 (15)
O1	0.0536 (13)	0.0898 (18)	0.0766 (17)	−0.0097 (12)	−0.0085 (12)	−0.0154 (16)
N2	0.0566 (17)	0.0606 (18)	0.098 (3)	0.0093 (14)	0.0178 (17)	−0.0109 (18)
C3	0.0466 (15)	0.0568 (18)	0.079 (2)	0.0019 (15)	0.0108 (16)	0.0012 (19)
C19	0.0610 (19)	0.073 (2)	0.0473 (18)	0.0030 (17)	0.0080 (15)	0.0067 (17)
C25	0.0488 (16)	0.0601 (19)	0.062 (2)	0.0031 (16)	0.0024 (14)	0.0063 (17)
C22	0.076 (2)	0.079 (3)	0.057 (2)	0.002 (2)	−0.0033 (18)	0.0122 (19)
C20	0.0468 (16)	0.0541 (18)	0.059 (2)	−0.0053 (14)	0.0019 (14)	0.0006 (15)
N1	0.0489 (13)	0.0639 (16)	0.0489 (14)	0.0050 (12)	0.0020 (11)	0.0017 (12)
C21	0.0587 (18)	0.065 (2)	0.064 (2)	0.0120 (18)	0.0061 (16)	0.0046 (18)
O2	0.0639 (13)	0.0595 (14)	0.0767 (17)	0.0014 (11)	0.0066 (13)	−0.0103 (13)
C11	0.092 (3)	0.073 (2)	0.062 (2)	−0.013 (2)	0.009 (2)	−0.0177 (18)
C7	0.074 (2)	0.053 (2)	0.078 (3)	−0.0109 (18)	0.015 (2)	−0.0192 (19)
C12	0.070 (2)	0.059 (2)	0.070 (2)	−0.0077 (18)	0.0177 (18)	−0.0185 (17)
C23	0.067 (2)	0.059 (2)	0.063 (2)	−0.0085 (18)	0.0165 (17)	0.0013 (17)
C10	0.112 (3)	0.075 (3)	0.061 (2)	−0.036 (3)	0.022 (2)	−0.018 (2)
C2	0.063 (2)	0.079 (2)	0.084 (3)	0.0067 (18)	0.015 (2)	0.027 (2)
C15	0.0577 (19)	0.068 (2)	0.067 (2)	0.0012 (17)	0.0166 (17)	0.0052 (18)
C24	0.0630 (19)	0.0539 (18)	0.073 (2)	0.0058 (16)	0.0134 (18)	0.0053 (17)
C26	0.111 (3)	0.083 (3)	0.066 (3)	−0.013 (3)	0.020 (2)	−0.004 (2)
C18	0.074 (2)	0.117 (4)	0.047 (2)	0.020 (3)	−0.0015 (18)	0.008 (2)
C1	0.068 (2)	0.079 (3)	0.071 (2)	0.0099 (19)	−0.0113 (18)	0.014 (2)
C9	0.127 (4)	0.083 (3)	0.082 (4)	−0.036 (3)	0.051 (3)	−0.031 (3)
C8	0.078 (3)	0.067 (3)	0.113 (4)	−0.017 (2)	0.044 (3)	−0.026 (2)
C16	0.051 (2)	0.099 (3)	0.098 (4)	−0.017 (2)	0.012 (2)	−0.020 (3)
C5	0.069 (2)	0.065 (2)	0.143 (5)	0.0083 (19)	0.004 (3)	0.025 (3)
C6	0.065 (2)	0.066 (2)	0.138 (5)	0.010 (2)	0.016 (3)	−0.003 (3)
C17	0.060 (2)	0.162 (5)	0.067 (3)	0.005 (3)	−0.009 (2)	−0.024 (3)

Geometric parameters (Å, º)

Br1—C10	1.910 (5)	C11—H11	0.9300
S1—O2	1.418 (3)	C7—C12	1.393 (5)
S1—O1	1.427 (3)	C7—C8	1.411 (6)
S1—N1	1.619 (3)	C12—H12	0.9300
S1—C20	1.762 (4)	C23—C24	1.367 (6)
C14—C15	1.382 (5)	C23—C26	1.531 (6)
C14—C19	1.381 (5)	C10—C9	1.367 (8)
C14—C13	1.516 (4)	C2—C1	1.507 (6)
C4—N1	1.467 (4)	C2—C5	1.519 (7)
C4—C13	1.526 (4)	C2—H2	0.9800
C4—C3	1.538 (5)	C15—C16	1.377 (6)
C4—H4	0.9800	C15—H15	0.9300
C13—H13A	0.9700	C24—H24	0.9300
C13—H13B	0.9700	C26—H26A	0.9600
N2—C7	1.354 (6)	C26—H26B	0.9600
N2—C6	1.452 (6)	C26—H26C	0.9600
N2—C3	1.479 (5)	C18—C17	1.366 (8)
C3—C2	1.526 (6)	C18—H18	0.9300
C3—H3	0.9800	C1—H1A	0.9700
C19—C18	1.391 (5)	C1—H1B	0.9700
C19—H19	0.9300	C9—C8	1.356 (8)
C25—C20	1.367 (5)	C9—H9	0.9300
C25—C24	1.370 (5)	C8—H8	0.9300
C25—H25	0.9300	C16—C17	1.378 (8)
C22—C23	1.378 (6)	C16—H16	0.9300
C22—C21	1.373 (6)	C5—C6	1.490 (8)
C22—H22	0.9300	C5—H5A	0.9700
C20—C21	1.395 (5)	C5—H5B	0.9700
N1—C1	1.485 (5)	C6—H6A	0.9700
C21—H21	0.9300	C6—H6B	0.9700
C11—C10	1.388 (6)	C17—H17	0.9300
C11—C12	1.386 (6)
O2—S1—O1	120.2 (2)	C22—C23—C24	118.5 (4)
O2—S1—N1	106.9 (2)	C22—C23—C26	120.7 (4)
O1—S1—N1	106.7 (2)	C24—C23—C26	120.8 (4)
O2—S1—C20	107.5 (2)	C9—C10—C11	121.2 (5)
O1—S1—C20	108.2 (2)	C9—C10—Br1	120.1 (4)
N1—S1—C20	106.6 (2)	C11—C10—Br1	118.7 (4)
C15—C14—C19	118.4 (3)	C1—C2—C5	113.5 (3)
C15—C14—C13	122.1 (3)	C1—C2—C3	105.1 (3)
C19—C14—C13	119.5 (3)	C5—C2—C3	103.8 (4)
N1—C4—C13	110.9 (3)	C1—C2—H2	111.3
N1—C4—C3	103.8 (3)	C5—C2—H2	111.3
C13—C4—C3	113.2 (3)	C3—C2—H2	111.3
N1—C4—H4	109.6	C16—C15—C14	120.7 (4)
C13—C4—H4	109.6	C16—C15—H15	119.6
C3—C4—H4	109.6	C14—C15—H15	119.6
C14—C13—C4	111.6 (3)	C23—C24—C25	121.4 (3)
C14—C13—H13A	109.3	C23—C24—H24	119.3
C4—C13—H13A	109.3	C25—C24—H24	119.3
C14—C13—H13B	109.3	C23—C26—H26A	109.5
C4—C13—H13B	109.3	C23—C26—H26B	109.5
H13A—C13—H13B	108.0	H26A—C26—H26B	109.5
C7—N2—C6	122.0 (4)	C23—C26—H26C	109.5
C7—N2—C3	123.7 (3)	H26A—C26—H26C	109.5
C6—N2—C3	111.3 (4)	H26B—C26—H26C	109.5
N2—C3—C2	102.7 (3)	C17—C18—C19	120.0 (4)
N2—C3—C4	113.3 (3)	C17—C18—H18	120.0
C2—C3—C4	105.4 (3)	C19—C18—H18	120.0
N2—C3—H3	111.7	N1—C1—C2	105.3 (3)
C2—C3—H3	111.7	N1—C1—H1A	110.7
C4—C3—H3	111.7	C2—C1—H1A	110.7
C18—C19—C14	120.8 (4)	N1—C1—H1B	110.7
C18—C19—H19	119.6	C2—C1—H1B	110.7
C14—C19—H19	119.6	H1A—C1—H1B	108.8
C20—C25—C24	119.8 (3)	C8—C9—C10	119.4 (4)
C20—C25—H25	120.1	C8—C9—H9	120.3
C24—C25—H25	120.1	C10—C9—H9	120.3
C23—C22—C21	121.6 (4)	C9—C8—C7	122.9 (5)
C23—C22—H22	119.2	C9—C8—H8	118.5
C21—C22—H22	119.2	C7—C8—H8	118.5
C25—C20—C21	120.1 (3)	C15—C16—C17	120.5 (4)
C25—C20—S1	120.8 (3)	C15—C16—H16	119.8
C21—C20—S1	119.0 (3)	C17—C16—H16	119.8
C4—N1—C1	111.9 (3)	C6—C5—C2	104.1 (4)
C4—N1—S1	118.7 (2)	C6—C5—H5A	110.9
C1—N1—S1	119.5 (2)	C2—C5—H5A	110.9
C22—C21—C20	118.6 (3)	C6—C5—H5B	110.9
C22—C21—H21	120.7	C2—C5—H5B	110.9
C20—C21—H21	120.7	H5A—C5—H5B	109.0
C10—C11—C12	118.2 (5)	N2—C6—C5	105.5 (4)
C10—C11—H11	120.9	N2—C6—H6A	110.6
C12—C11—H11	120.9	C5—C6—H6A	110.6
N2—C7—C12	122.0 (3)	N2—C6—H6B	110.6
N2—C7—C8	122.4 (4)	C5—C6—H6B	110.6
C12—C7—C8	115.6 (5)	H6A—C6—H6B	108.8
C11—C12—C7	122.7 (4)	C18—C17—C16	119.6 (4)
C11—C12—H12	118.7	C18—C17—H17	120.2
C7—C12—H12	118.7	C16—C17—H17	120.2
C15—C14—C13—C4	−100.6 (4)	C6—N2—C7—C8	18.5 (6)
C19—C14—C13—C4	75.6 (4)	C3—N2—C7—C8	177.3 (3)
N1—C4—C13—C14	−169.8 (3)	C10—C11—C12—C7	−0.6 (6)
C3—C4—C13—C14	74.0 (4)	N2—C7—C12—C11	−179.0 (4)
C7—N2—C3—C2	−175.3 (4)	C8—C7—C12—C11	1.6 (5)
C6—N2—C3—C2	−14.5 (4)	C21—C22—C23—C24	0.4 (6)
C7—N2—C3—C4	71.6 (4)	C21—C22—C23—C26	−179.6 (4)
C6—N2—C3—C4	−127.6 (3)	C12—C11—C10—C9	−1.1 (6)
N1—C4—C3—N2	86.4 (4)	C12—C11—C10—Br1	−179.7 (3)
C13—C4—C3—N2	−153.3 (3)	N2—C3—C2—C1	−89.1 (4)
N1—C4—C3—C2	−25.1 (3)	C4—C3—C2—C1	29.8 (4)
C13—C4—C3—C2	95.2 (3)	N2—C3—C2—C5	30.4 (4)
C15—C14—C19—C18	−0.3 (5)	C4—C3—C2—C5	149.3 (3)
C13—C14—C19—C18	−176.7 (3)	C19—C14—C15—C16	−0.5 (5)
C24—C25—C20—C21	1.3 (5)	C13—C14—C15—C16	175.8 (3)
C24—C25—C20—S1	−175.0 (3)	C22—C23—C24—C25	−0.5 (5)
O2—S1—C20—C25	−165.6 (3)	C26—C23—C24—C25	179.5 (4)
O1—S1—C20—C25	−34.4 (3)	C20—C25—C24—C23	−0.3 (5)
N1—S1—C20—C25	80.1 (3)	C14—C19—C18—C17	1.8 (6)
O2—S1—C20—C21	18.1 (3)	C4—N1—C1—C2	6.9 (4)
O1—S1—C20—C21	149.3 (3)	S1—N1—C1—C2	152.3 (3)
N1—S1—C20—C21	−96.2 (3)	C5—C2—C1—N1	−135.3 (4)
C13—C4—N1—C1	−110.5 (3)	C3—C2—C1—N1	−22.5 (4)
C3—C4—N1—C1	11.4 (4)	C11—C10—C9—C8	1.7 (7)
C13—C4—N1—S1	103.8 (3)	Br1—C10—C9—C8	−179.7 (3)
C3—C4—N1—S1	−134.3 (2)	C10—C9—C8—C7	−0.7 (7)
O2—S1—N1—C4	−54.6 (3)	N2—C7—C8—C9	179.6 (4)
O1—S1—N1—C4	175.6 (2)	C12—C7—C8—C9	−1.0 (6)
C20—S1—N1—C4	60.2 (3)	C14—C15—C16—C17	−0.3 (6)
O2—S1—N1—C1	162.3 (3)	C1—C2—C5—C6	77.8 (5)
O1—S1—N1—C1	32.6 (3)	C3—C2—C5—C6	−35.8 (4)
C20—S1—N1—C1	−82.9 (3)	C7—N2—C6—C5	153.5 (4)
C23—C22—C21—C20	0.5 (6)	C3—N2—C6—C5	−7.7 (5)
C25—C20—C21—C22	−1.4 (5)	C2—C5—C6—N2	26.8 (5)
S1—C20—C21—C22	175.0 (3)	C19—C18—C17—C16	−2.6 (7)
C6—N2—C7—C12	−160.9 (3)	C15—C16—C17—C18	1.8 (7)
C3—N2—C7—C12	−2.1 (6)