cis-1-(4-Bromo­phen­yl)-6-ethyl-5-tosylperhydro­pyrrolo[3,4-b]pyrrole

In the title mol­ecule, C₂₁H₂₅BrN₂O₂S, one of the fused pyrrolidine rings adopts an envelope conformation, while the other is in a twist conformation. In the crystal structure, mol­ecules related by translation along the a axis are linked by π–π inter­actions into a chain.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.147
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Datablock: pc451



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.84
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14

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           30.34
           From the CIF: _reflns_number_total               5855
           Count of symmetry unique reflns         3069
           Completeness (_total/calc)            190.78%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2786
           Fraction of Friedel pairs measured     0.908
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C3     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C4     = ...          R

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

   3 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
   0 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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

cis-1-(4-Bromophenyl)-6-ethyl-5-tosylperhydropyrrolo[3,4-b]pyrrole

Crystal data

C21H25BrN2O2S	F(000) = 928
Mr = 449.40	Dx = 1.520 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4939 reflections
a = 7.7131 (3) Å	θ = 2.8–28.9°
b = 19.6640 (8) Å	µ = 2.22 mm^−1
c = 12.9518 (4) Å	T = 100 K
V = 1964.40 (13) Å^3	Plate, colourless
Z = 4	0.28 × 0.27 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	5855 independent reflections
Radiation source: fine-focus sealed tube	4509 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 8.33 pixels mm^-1	θmax = 30.3°, θmin = 1.9°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −27→21
Tmin = 0.531, Tmax = 0.869	l = −18→18
21230 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0868P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5855 reflections	Δρmax = 2.61 e Å^−3
246 parameters	Δρmin = −0.92 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 2795 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.005 (11)

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	0.65850 (6)	0.27316 (2)	0.73686 (5)	0.03226 (13)
S1	1.30353 (12)	0.62475 (5)	0.84750 (8)	0.01765 (19)
O1	1.4246 (4)	0.66977 (16)	0.8969 (2)	0.0246 (6)
O2	1.3026 (3)	0.61741 (15)	0.7375 (3)	0.0242 (6)
N1	1.1115 (4)	0.65048 (17)	0.8808 (2)	0.0173 (7)
N2	0.8939 (4)	0.52915 (18)	0.9593 (3)	0.0186 (7)
C1	1.0800 (5)	0.6678 (2)	0.9908 (3)	0.0195 (8)
H1A	1.0904	0.7174	1.0019	0.023*
H1B	1.1645	0.6443	1.0360	0.023*
C2	0.8948 (5)	0.6436 (2)	1.0142 (3)	0.0184 (8)
H2	0.8131	0.6829	1.0197	0.022*
C3	0.8459 (5)	0.5971 (2)	0.9234 (3)	0.0161 (7)
H3	0.7189	0.5997	0.9085	0.019*
C4	0.9521 (4)	0.6221 (2)	0.8316 (3)	0.0145 (7)
H4	0.9824	0.5834	0.7850	0.017*
C5	0.8814 (5)	0.5972 (2)	1.1088 (3)	0.0218 (8)
H5A	0.9575	0.6135	1.1652	0.026*
H5B	0.7606	0.5950	1.1344	0.026*
C6	0.9412 (6)	0.5279 (2)	1.0694 (3)	0.0220 (8)
H6A	1.0679	0.5223	1.0783	0.026*
H6B	0.8808	0.4906	1.1060	0.026*
C7	0.8467 (5)	0.4712 (2)	0.9066 (3)	0.0192 (8)
C8	0.7543 (5)	0.4751 (2)	0.8125 (3)	0.0190 (8)
H8	0.7284	0.5182	0.7832	0.023*
C9	0.7018 (5)	0.4163 (2)	0.7631 (3)	0.0224 (9)
H9	0.6374	0.4194	0.7008	0.027*
C10	0.7416 (5)	0.3530 (2)	0.8032 (3)	0.0219 (8)
C11	0.8375 (5)	0.3476 (2)	0.8943 (4)	0.0245 (9)
H11	0.8671	0.3043	0.9216	0.029*
C12	0.8885 (5)	0.4065 (2)	0.9439 (3)	0.0224 (8)
H12	0.9544	0.4030	1.0057	0.027*
C13	1.3383 (5)	0.5432 (2)	0.8998 (3)	0.0171 (7)
C14	1.4259 (5)	0.5356 (2)	0.9933 (3)	0.0183 (8)
H14	1.4666	0.5744	1.0296	0.022*
C15	1.4530 (5)	0.4709 (2)	1.0328 (3)	0.0216 (8)
H15	1.5116	0.4657	1.0968	0.026*
C16	1.3956 (5)	0.4132 (2)	0.9801 (3)	0.0198 (8)
C17	1.3079 (5)	0.4222 (2)	0.8865 (3)	0.0216 (8)
H17	1.2670	0.3835	0.8500	0.026*
C18	1.2797 (5)	0.4862 (2)	0.8464 (3)	0.0204 (8)
H18	1.2205	0.4914	0.7825	0.024*
C19	1.4281 (6)	0.3434 (2)	1.0218 (4)	0.0257 (9)
H19A	1.4810	0.3469	1.0904	0.039*
H19B	1.5066	0.3189	0.9754	0.039*
H19C	1.3180	0.3188	1.0270	0.039*
C20	0.8535 (5)	0.6766 (2)	0.7724 (3)	0.0186 (8)
H20A	0.7487	0.6558	0.7418	0.022*
H20B	0.8146	0.7119	0.8219	0.022*
C21	0.9564 (5)	0.7110 (2)	0.6870 (3)	0.0215 (8)
H21A	0.8797	0.7410	0.6474	0.032*
H21B	1.0053	0.6763	0.6411	0.032*
H21C	1.0505	0.7378	0.7174	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0314 (2)	0.0318 (2)	0.0336 (2)	−0.00821 (17)	0.0041 (2)	−0.0073 (2)
S1	0.0084 (3)	0.0280 (5)	0.0166 (4)	0.0015 (3)	0.0022 (3)	0.0046 (4)
O1	0.0112 (13)	0.0313 (16)	0.0312 (17)	−0.0022 (12)	−0.0030 (12)	0.0043 (13)
O2	0.0160 (12)	0.0404 (16)	0.0161 (12)	0.0067 (10)	0.0070 (14)	0.0075 (16)
N1	0.0087 (14)	0.0293 (18)	0.0138 (15)	−0.0003 (12)	−0.0009 (12)	0.0002 (13)
N2	0.0158 (15)	0.0276 (18)	0.0126 (15)	−0.0004 (13)	−0.0011 (12)	0.0037 (13)
C1	0.0134 (18)	0.030 (2)	0.0151 (17)	−0.0021 (15)	−0.0008 (14)	−0.0024 (15)
C2	0.0117 (17)	0.028 (2)	0.0157 (18)	0.0015 (15)	0.0017 (13)	−0.0027 (15)
C3	0.0099 (16)	0.0227 (19)	0.0157 (17)	−0.0009 (14)	−0.0019 (13)	0.0031 (14)
C4	0.0038 (14)	0.0249 (18)	0.0149 (17)	−0.0006 (13)	−0.0016 (12)	0.0017 (14)
C5	0.0159 (18)	0.035 (2)	0.0144 (18)	0.0022 (16)	0.0006 (15)	−0.0018 (16)
C6	0.021 (2)	0.030 (2)	0.0149 (18)	0.0008 (16)	−0.0018 (15)	0.0046 (16)
C7	0.0120 (17)	0.026 (2)	0.0192 (18)	−0.0009 (15)	0.0049 (14)	0.0022 (15)
C8	0.0120 (16)	0.027 (2)	0.0182 (18)	−0.0016 (15)	0.0012 (14)	0.0040 (15)
C9	0.0133 (18)	0.036 (2)	0.018 (2)	−0.0007 (15)	0.0028 (13)	−0.0018 (16)
C10	0.0178 (18)	0.026 (2)	0.0217 (19)	−0.0029 (16)	0.0078 (16)	−0.0044 (16)
C11	0.0182 (19)	0.026 (2)	0.030 (2)	−0.0001 (16)	0.0036 (17)	0.0039 (17)
C12	0.0186 (19)	0.027 (2)	0.021 (2)	−0.0009 (16)	−0.0007 (16)	0.0050 (17)
C13	0.0105 (17)	0.0199 (18)	0.0208 (19)	0.0026 (13)	0.0011 (14)	0.0033 (15)
C14	0.0099 (17)	0.029 (2)	0.0162 (18)	−0.0010 (14)	−0.0001 (14)	−0.0005 (15)
C15	0.0107 (17)	0.041 (2)	0.0131 (17)	0.0022 (16)	0.0009 (14)	0.0026 (17)
C16	0.0105 (16)	0.031 (2)	0.0179 (18)	0.0038 (15)	0.0049 (14)	0.0077 (16)
C17	0.0147 (18)	0.030 (2)	0.0203 (19)	0.0003 (15)	0.0002 (15)	−0.0031 (17)
C18	0.0132 (17)	0.033 (2)	0.0153 (17)	0.0013 (15)	−0.0016 (15)	−0.0002 (17)
C19	0.023 (2)	0.030 (2)	0.024 (2)	0.0023 (18)	0.0046 (17)	0.0034 (17)
C20	0.0138 (17)	0.025 (2)	0.0171 (16)	0.0007 (14)	−0.0030 (14)	0.0023 (15)
C21	0.0163 (19)	0.029 (2)	0.0194 (19)	−0.0026 (15)	−0.0033 (16)	0.0061 (16)

Geometric parameters (Å, º)

Br1—C10	1.901 (4)	C8—H8	0.95
S1—O2	1.432 (4)	C9—C10	1.383 (6)
S1—O1	1.437 (3)	C9—H9	0.95
S1—N1	1.623 (3)	C10—C11	1.397 (6)
S1—C13	1.762 (4)	C11—C12	1.382 (6)
N1—C1	1.485 (5)	C11—H11	0.95
N1—C4	1.493 (5)	C12—H12	0.95
N2—C7	1.378 (6)	C13—C18	1.392 (6)
N2—C3	1.462 (5)	C13—C14	1.395 (6)
N2—C6	1.473 (5)	C14—C15	1.388 (6)
C1—C2	1.536 (5)	C14—H14	0.95
C1—H1A	0.99	C15—C16	1.395 (6)
C1—H1B	0.99	C15—H15	0.95
C2—C5	1.532 (6)	C16—C17	1.399 (6)
C2—C3	1.536 (5)	C16—C19	1.497 (6)
C2—H2	1.00	C17—C18	1.379 (6)
C3—C4	1.526 (5)	C17—H17	0.95
C3—H3	1.00	C18—H18	0.95
C4—C20	1.521 (5)	C19—H19A	0.98
C4—H4	1.00	C19—H19B	0.98
C5—C6	1.525 (6)	C19—H19C	0.98
C5—H5A	0.99	C20—C21	1.520 (6)
C5—H5B	0.99	C20—H20A	0.99
C6—H6A	0.99	C20—H20B	0.99
C6—H6B	0.99	C21—H21A	0.98
C7—C12	1.398 (6)	C21—H21B	0.98
C7—C8	1.413 (6)	C21—H21C	0.98
C8—C9	1.382 (6)
O2—S1—O1	120.55 (18)	C9—C8—C7	120.1 (4)
O2—S1—N1	106.95 (16)	C9—C8—H8	120.0
O1—S1—N1	106.40 (18)	C7—C8—H8	120.0
O2—S1—C13	106.95 (19)	C8—C9—C10	120.9 (4)
O1—S1—C13	106.90 (19)	C8—C9—H9	119.5
N1—S1—C13	108.69 (18)	C10—C9—H9	119.5
C1—N1—C4	111.1 (3)	C9—C10—C11	120.2 (4)
C1—N1—S1	118.4 (3)	C9—C10—Br1	119.9 (3)
C4—N1—S1	121.4 (3)	C11—C10—Br1	119.9 (3)
C7—N2—C3	122.1 (3)	C12—C11—C10	118.7 (4)
C7—N2—C6	122.1 (3)	C12—C11—H11	120.7
C3—N2—C6	112.7 (3)	C10—C11—H11	120.7
N1—C1—C2	105.7 (3)	C11—C12—C7	122.4 (4)
N1—C1—H1A	110.6	C11—C12—H12	118.8
C2—C1—H1A	110.6	C7—C12—H12	118.8
N1—C1—H1B	110.6	C18—C13—C14	120.2 (4)
C2—C1—H1B	110.6	C18—C13—S1	119.5 (3)
H1A—C1—H1B	108.7	C14—C13—S1	120.3 (3)
C5—C2—C3	103.9 (3)	C15—C14—C13	119.4 (4)
C5—C2—C1	113.8 (3)	C15—C14—H14	120.3
C3—C2—C1	105.2 (3)	C13—C14—H14	120.3
C5—C2—H2	111.2	C14—C15—C16	121.1 (4)
C3—C2—H2	111.2	C14—C15—H15	119.4
C1—C2—H2	111.2	C16—C15—H15	119.4
N2—C3—C4	114.0 (3)	C15—C16—C17	118.3 (4)
N2—C3—C2	103.8 (3)	C15—C16—C19	121.0 (4)
C4—C3—C2	105.8 (3)	C17—C16—C19	120.6 (4)
N2—C3—H3	111.0	C18—C17—C16	121.2 (4)
C4—C3—H3	111.0	C18—C17—H17	119.4
C2—C3—H3	111.0	C16—C17—H17	119.4
N1—C4—C20	111.3 (3)	C17—C18—C13	119.7 (4)
N1—C4—C3	103.3 (3)	C17—C18—H18	120.1
C20—C4—C3	110.6 (3)	C13—C18—H18	120.1
N1—C4—H4	110.5	C16—C19—H19A	109.5
C20—C4—H4	110.5	C16—C19—H19B	109.5
C3—C4—H4	110.5	H19A—C19—H19B	109.5
C6—C5—C2	104.1 (3)	C16—C19—H19C	109.5
C6—C5—H5A	110.9	H19A—C19—H19C	109.5
C2—C5—H5A	110.9	H19B—C19—H19C	109.5
C6—C5—H5B	110.9	C21—C20—C4	114.8 (3)
C2—C5—H5B	110.9	C21—C20—H20A	108.6
H5A—C5—H5B	109.0	C4—C20—H20A	108.6
N2—C6—C5	103.6 (3)	C21—C20—H20B	108.6
N2—C6—H6A	111.0	C4—C20—H20B	108.6
C5—C6—H6A	111.0	H20A—C20—H20B	107.6
N2—C6—H6B	111.0	C20—C21—H21A	109.5
C5—C6—H6B	111.0	C20—C21—H21B	109.5
H6A—C6—H6B	109.0	H21A—C21—H21B	109.5
N2—C7—C12	121.3 (4)	C20—C21—H21C	109.5
N2—C7—C8	121.0 (4)	H21A—C21—H21C	109.5
C12—C7—C8	117.7 (4)	H21B—C21—H21C	109.5
O2—S1—N1—C1	−175.1 (3)	C6—N2—C7—C12	−19.0 (6)
O1—S1—N1—C1	−45.0 (3)	C3—N2—C7—C8	2.4 (6)
C13—S1—N1—C1	69.8 (3)	C6—N2—C7—C8	161.1 (4)
O2—S1—N1—C4	40.8 (3)	N2—C7—C8—C9	−177.2 (4)
O1—S1—N1—C4	170.8 (3)	C12—C7—C8—C9	2.9 (5)
C13—S1—N1—C4	−74.4 (3)	C7—C8—C9—C10	−1.5 (6)
C4—N1—C1—C2	4.7 (4)	C8—C9—C10—C11	−0.6 (6)
S1—N1—C1—C2	−143.0 (3)	C8—C9—C10—Br1	177.1 (3)
N1—C1—C2—C5	127.2 (4)	C9—C10—C11—C12	1.1 (6)
N1—C1—C2—C3	14.1 (4)	Br1—C10—C11—C12	−176.6 (3)
C7—N2—C3—C4	−75.5 (4)	C10—C11—C12—C7	0.4 (6)
C6—N2—C3—C4	123.9 (4)	N2—C7—C12—C11	177.7 (4)
C7—N2—C3—C2	169.9 (3)	C8—C7—C12—C11	−2.4 (6)
C6—N2—C3—C2	9.3 (4)	O2—S1—C13—C18	−30.1 (4)
C5—C2—C3—N2	−27.1 (4)	O1—S1—C13—C18	−160.5 (3)
C1—C2—C3—N2	92.9 (4)	N1—S1—C13—C18	85.1 (3)
C5—C2—C3—C4	−147.4 (3)	O2—S1—C13—C14	149.1 (3)
C1—C2—C3—C4	−27.4 (4)	O1—S1—C13—C14	18.7 (4)
C1—N1—C4—C20	97.2 (4)	N1—S1—C13—C14	−95.8 (3)
S1—N1—C4—C20	−116.3 (3)	C18—C13—C14—C15	−0.4 (6)
C1—N1—C4—C3	−21.5 (4)	S1—C13—C14—C15	−179.6 (3)
S1—N1—C4—C3	125.0 (3)	C13—C14—C15—C16	0.6 (6)
N2—C3—C4—N1	−83.8 (4)	C14—C15—C16—C17	−0.7 (6)
C2—C3—C4—N1	29.7 (4)	C14—C15—C16—C19	178.8 (4)
N2—C3—C4—C20	157.0 (3)	C15—C16—C17—C18	0.6 (6)
C2—C3—C4—C20	−89.5 (4)	C19—C16—C17—C18	−178.9 (4)
C3—C2—C5—C6	34.9 (4)	C16—C17—C18—C13	−0.4 (6)
C1—C2—C5—C6	−79.0 (4)	C14—C13—C18—C17	0.3 (6)
C7—N2—C6—C5	−148.2 (4)	S1—C13—C18—C17	179.4 (3)
C3—N2—C6—C5	12.3 (4)	N1—C4—C20—C21	58.9 (4)
C2—C5—C6—N2	−28.9 (4)	C3—C4—C20—C21	173.1 (3)
C3—N2—C7—C12	−177.7 (4)