1,2-Bis­[(2R,5R)-2,5-di­methyl­pyrrolidin-1-yl]­benzene

The title compound, C₁₈H₂₈N₂, with a crystallographic twofold rotation axis, can function as a C₂-symmetric di­amine ligand.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.084
• Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.30
         From the CIF: _reflns_number_total               1174
         Count of symmetry unique reflns         1185
         Completeness (_total/calc)             99.07%
         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
          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.

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Computing details

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I)

Crystal data

C18H28N2	F(000) = 300
Mr = 272.42	Dx = 1.119 Mg m^−3
Orthorhombic, P22121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2bc 2	Cell parameters from 11552 reflections
a = 8.5423 (2) Å	θ = 3.8–28.3°
b = 8.8892 (2) Å	µ = 0.07 mm^−1
c = 10.6486 (2) Å	T = 123 K
V = 808.59 (3) Å^3	Prismatic, colourless
Z = 2	0.25 × 0.2 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer	Rint = 0.043
CCD rotation images, thick slices scans	θmax = 28.3°, θmin = 3.8°
11552 measured reflections	h = −11→11
1174 independent reflections	k = −11→11
1094 reflections with I > 2σ(I)	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 0.1166P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.17 e Å^−3
1174 reflections	Δρmin = −0.16 e Å^−3
93 parameters	Absolute structure: Friedel opposites merged

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.56474 (15)	0.44913 (13)	0.05155 (11)	0.0217 (3)
C2	0.42130 (16)	0.40542 (15)	0.10227 (13)	0.0291 (3)
H2	0.4202	0.3407	0.1733	0.035*
C3	0.28012 (17)	0.45362 (16)	0.05207 (14)	0.0338 (3)
H3	0.1840	0.4231	0.0890	0.041*
C4	0.71578 (17)	0.33212 (16)	0.22648 (13)	0.0314 (3)
H4	0.6418	0.2453	0.2331	0.038*
C5	0.88399 (18)	0.27523 (19)	0.23052 (16)	0.0388 (4)
H5A	0.9584	0.3588	0.2451	0.047*
H5B	0.8978	0.1986	0.2971	0.047*
C6	0.90611 (18)	0.20718 (16)	0.10109 (16)	0.0364 (4)
H6A	0.8656	0.1029	0.0986	0.044*
H6B	1.0182	0.2063	0.0775	0.044*
C7	0.81213 (14)	0.30934 (14)	0.01259 (13)	0.0257 (3)
H7	0.8853	0.3803	−0.0306	0.031*
C8	0.6788 (2)	0.4468 (2)	0.32756 (13)	0.0441 (4)
H8A	0.7543	0.5296	0.3230	0.066*
H8B	0.6855	0.3988	0.4102	0.066*
H8C	0.5728	0.4860	0.3148	0.066*
C9	0.72306 (18)	0.21970 (16)	−0.08556 (15)	0.0345 (3)
H9A	0.6495	0.1515	−0.0438	0.052*
H9B	0.7971	0.1611	−0.1360	0.052*
H9C	0.6651	0.2887	−0.1402	0.052*
N1	0.70859 (13)	0.39613 (11)	0.09903 (10)	0.0227 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0227 (6)	0.0206 (5)	0.0219 (5)	−0.0018 (5)	−0.0009 (5)	−0.0023 (5)
C2	0.0289 (7)	0.0290 (6)	0.0293 (6)	−0.0064 (5)	0.0037 (6)	−0.0004 (6)
C3	0.0228 (6)	0.0363 (7)	0.0423 (7)	−0.0040 (6)	0.0046 (6)	−0.0069 (7)
C4	0.0337 (7)	0.0354 (7)	0.0252 (6)	−0.0106 (6)	−0.0062 (6)	0.0117 (6)
C5	0.0365 (8)	0.0394 (8)	0.0406 (8)	−0.0075 (7)	−0.0142 (7)	0.0168 (7)
C6	0.0317 (7)	0.0256 (6)	0.0518 (9)	0.0001 (6)	−0.0118 (7)	0.0089 (7)
C7	0.0243 (6)	0.0200 (5)	0.0327 (7)	0.0008 (5)	−0.0022 (6)	0.0012 (5)
C8	0.0501 (10)	0.0596 (10)	0.0225 (6)	−0.0139 (9)	−0.0016 (7)	0.0018 (8)
C9	0.0367 (8)	0.0278 (6)	0.0389 (8)	0.0070 (6)	−0.0071 (7)	−0.0094 (7)
N1	0.0239 (5)	0.0240 (5)	0.0202 (5)	−0.0014 (4)	−0.0011 (4)	0.0033 (5)

Geometric parameters (Å, º)

C1—C2	1.3943 (18)	C5—H5B	0.9900
C1—N1	1.4098 (16)	C6—C7	1.5354 (19)
C1—C1^i	1.422 (2)	C6—H6A	0.9900
C2—C3	1.387 (2)	C6—H6B	0.9900
C2—H2	0.9500	C7—N1	1.4915 (17)
C3—C3^i	1.382 (3)	C7—C9	1.5186 (19)
C3—H3	0.9500	C7—H7	1.0000
C4—N1	1.4729 (16)	C8—H8A	0.9800
C4—C8	1.515 (2)	C8—H8B	0.9800
C4—C5	1.524 (2)	C8—H8C	0.9800
C4—H4	1.0000	C9—H9A	0.9800
C5—C6	1.517 (2)	C9—H9B	0.9800
C5—H5A	0.9900	C9—H9C	0.9800
C2—C1—N1	122.27 (11)	C5—C6—H6B	110.8
C2—C1—C1^i	118.43 (8)	C7—C6—H6B	110.8
N1—C1—C1^i	119.29 (6)	H6A—C6—H6B	108.8
C3—C2—C1	121.92 (12)	N1—C7—C9	113.52 (10)
C3—C2—H2	119.0	N1—C7—C6	103.72 (11)
C1—C2—H2	119.0	C9—C7—C6	111.97 (11)
C3^i—C3—C2	119.58 (8)	N1—C7—H7	109.2
C3^i—C3—H3	120.2	C9—C7—H7	109.2
C2—C3—H3	120.2	C6—C7—H7	109.2
N1—C4—C8	112.70 (12)	C4—C8—H8A	109.5
N1—C4—C5	101.16 (12)	C4—C8—H8B	109.5
C8—C4—C5	113.54 (13)	H8A—C8—H8B	109.5
N1—C4—H4	109.7	C4—C8—H8C	109.5
C8—C4—H4	109.7	H8A—C8—H8C	109.5
C5—C4—H4	109.7	H8B—C8—H8C	109.5
C6—C5—C4	102.95 (12)	C7—C9—H9A	109.5
C6—C5—H5A	111.2	C7—C9—H9B	109.5
C4—C5—H5A	111.2	H9A—C9—H9B	109.5
C6—C5—H5B	111.2	C7—C9—H9C	109.5
C4—C5—H5B	111.2	H9A—C9—H9C	109.5
H5A—C5—H5B	109.1	H9B—C9—H9C	109.5
C5—C6—C7	104.87 (12)	C1—N1—C4	119.73 (11)
C5—C6—H6A	110.8	C1—N1—C7	117.93 (10)
C7—C6—H6A	110.8	C4—N1—C7	110.13 (10)

Symmetry code: (i) x, −y+1, −z.