1,4-Bis(1-naphthyl­meth­yl)piperazine

Kubo, K.; Yamamoto, E.; Hayakawa, A.; Sakurai, T.; Mori, A.

doi:10.1107/S1600536807007118

1,4-Bis(1-naphthylmethyl)piperazine

K. Kubo, E. Yamamoto, A. Hayakawa, T. Sakurai and A. Mori

The molecule of the title compound, C₂₆H₂₆N₂, sits on a center of symmetry such that the two naphthalene ring systems are in an anti conformation with respect to one another across the piperazine ring. An intermolecular π–π interaction between the naphthalene ring systems is observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007118/fl2101sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007118/fl2101Isup2.hkl Contains datablock I

CCDC reference: 640329

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.005 Å
R factor = 0.074
wR factor = 0.249
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.671     0.946
            Tmin(prime) and Tmax expected:      0.816     0.946
            RR(prime) =      0.822
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   1 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
   3 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 top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: please supply; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Macrae et al., 2006); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

1,4-Bis(1-naphthylmethyl)piperazine top

Crystal data top

C₂₆H₂₆N₂	F(000) = 392.00
M_r = 366.50	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/a	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yab	Cell parameters from 8164 reflections
a = 11.300 (4) Å	θ = 4.1–68.2°
b = 5.5286 (18) Å	µ = 0.56 mm⁻¹
c = 16.141 (5) Å	T = 153 K
β = 106.856 (18)°	Plate, colourless
V = 965.1 (5) Å³	0.32 × 0.28 × 0.10 mm
Z = 2

Data collection top

Rigaku RAXIS-RAPID diffractometer	1463 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.057
ω scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.671, T_max = 0.946	k = −6→6
8585 measured reflections	l = −19→18
1733 independent reflections

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.0773P)² + 2.3943P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.074	(Δ/σ)_max < 0.001
wR(F²) = 0.249	Δρ_max = 0.40 e Å⁻³
S = 1.23	Δρ_min = −0.23 e Å⁻³
1733 reflections	Extinction correction: SHELXL97
129 parameters	Extinction coefficient: 0.013 (2)
H-atom parameters constrained

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.9652 (2)	0.9302 (5)	0.07594 (17)	0.0248 (7)
C1	1.0187 (3)	0.7891 (6)	0.2291 (2)	0.0254 (8)
C2	1.1143 (3)	0.6373 (6)	0.2677 (2)	0.0293 (8)
C3	1.1844 (3)	0.6651 (7)	0.3550 (2)	0.0310 (9)
C4	1.1539 (3)	0.8418 (7)	0.4040 (2)	0.0299 (9)
C5	1.0552 (3)	1.0035 (6)	0.3674 (2)	0.0264 (8)
C6	1.0214 (3)	1.1868 (7)	0.4176 (2)	0.0311 (9)
C7	0.9274 (3)	1.3415 (7)	0.3825 (2)	0.0337 (9)
C8	0.8603 (3)	1.3222 (7)	0.2939 (2)	0.0331 (9)
C9	0.8899 (3)	1.1476 (6)	0.2433 (2)	0.0288 (8)
C10	0.9870 (3)	0.9805 (6)	0.2784 (2)	0.0255 (8)
C11	0.9450 (3)	0.7472 (7)	0.1359 (2)	0.0271 (8)
C12	0.8844 (3)	0.8868 (7)	−0.0112 (2)	0.0289 (9)
C13	0.9052 (3)	1.0749 (7)	−0.0738 (2)	0.0271 (8)
H1	1.1342	0.5094	0.2348	0.035*
H2	1.2525	0.5611	0.3795	0.037*
H3	1.1993	0.8568	0.4633	0.036*
H4	1.0657	1.2014	0.4772	0.037*
H5	0.9065	1.4632	0.4174	0.040*
H6	0.7944	1.4310	0.2695	0.040*
H7	0.8449	1.1379	0.1837	0.035*
H8	0.9669	0.5866	0.1176	0.033*
H9	0.8559	0.7441	0.1321	0.033*
H10	0.7970	0.8922	−0.0106	0.035*
H(11)	0.9008	0.7237	−0.0307	0.035*
H12	0.8494	1.0425	−0.1324	0.033*
H13	0.8854	1.2374	−0.0557	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0237 (15)	0.0312 (17)	0.0197 (14)	−0.0014 (12)	0.0065 (11)	−0.0012 (12)
C1	0.0251 (17)	0.0287 (19)	0.0236 (17)	−0.0037 (14)	0.0091 (13)	0.0016 (14)
C2	0.0302 (19)	0.0291 (19)	0.0299 (19)	0.0012 (15)	0.0107 (15)	0.0001 (15)
C3	0.0284 (19)	0.034 (2)	0.0306 (19)	0.0039 (16)	0.0089 (15)	0.0060 (16)
C4	0.0276 (19)	0.036 (2)	0.0233 (17)	−0.0034 (15)	0.0033 (14)	0.0025 (15)
C5	0.0250 (17)	0.030 (2)	0.0257 (18)	−0.0059 (14)	0.0098 (13)	0.0018 (14)
C6	0.034 (2)	0.034 (2)	0.0265 (19)	−0.0056 (16)	0.0105 (15)	−0.0025 (15)
C7	0.039 (2)	0.029 (2)	0.037 (2)	−0.0034 (17)	0.0174 (16)	−0.0055 (16)
C8	0.035 (2)	0.029 (2)	0.037 (2)	0.0019 (16)	0.0130 (16)	0.0045 (16)
C9	0.0279 (19)	0.032 (2)	0.0263 (18)	−0.0014 (15)	0.0079 (14)	0.0017 (14)
C10	0.0270 (18)	0.0262 (19)	0.0243 (17)	−0.0043 (14)	0.0091 (14)	0.0028 (13)
C11	0.0258 (17)	0.033 (2)	0.0247 (18)	−0.0032 (15)	0.0102 (14)	−0.0023 (14)
C12	0.0238 (17)	0.037 (2)	0.0252 (18)	−0.0031 (15)	0.0066 (13)	−0.0021 (15)
C13	0.0226 (17)	0.036 (2)	0.0217 (16)	−0.0012 (15)	0.0053 (12)	−0.0004 (14)

Geometric parameters (Å, º) top

N1—C11	1.463 (4)	C12—C13	1.515 (5)
N1—C12	1.458 (3)	C2—H1	0.950
N1—C13ⁱ	1.475 (4)	C3—H2	0.950
C1—C2	1.367 (4)	C4—H3	0.950
C1—C10	1.430 (5)	C6—H4	0.950
C1—C11	1.512 (4)	C7—H5	0.950
C2—C3	1.410 (4)	C8—H6	0.950
C3—C4	1.363 (5)	C9—H7	0.950
C4—C5	1.418 (4)	C11—H8	0.990
C5—C6	1.418 (5)	C11—H9	0.990
C5—C10	1.424 (4)	C12—H10	0.990
C6—C7	1.353 (5)	C12—H(11)	0.990
C7—C8	1.415 (5)	C13—H12	0.990
C8—C9	1.368 (5)	C13—H13	0.990
C9—C10	1.420 (4)

C1···C8ⁱⁱ	3.471 (5)	H3···H3^vii	3.094
C2···C7ⁱⁱ	3.583 (6)	H3···H4^vi	2.690
C2···C8ⁱⁱ	3.487 (5)	H3···H4^iv	3.414
C3···C6ⁱⁱ	3.534 (5)	H3···H5^iv	3.098
C3···C7ⁱⁱ	3.547 (5)	H3···H5^v	2.834
C6···C3ⁱⁱⁱ	3.534 (5)	H4···C3^vii	3.304
C6···C6^iv	3.510 (5)	H4···C4^vii	3.286
C7···C2ⁱⁱⁱ	3.583 (6)	H4···C4^iv	3.556
C7···C3ⁱⁱⁱ	3.547 (5)	H4···C5^iv	3.380
C8···C1ⁱⁱⁱ	3.471 (5)	H4···C6^iv	3.070
C8···C2ⁱⁱⁱ	3.487 (5)	H4···C7^ix	3.379
C1···H6ⁱⁱ	3.425	H4···H2ⁱⁱⁱ	3.582
C1···H6^v	3.368	H4···H2^vii	2.723
C2···H6^v	3.130	H4···H3^vii	2.690
C3···H3^vi	3.316	H4···H3^iv	3.414
C3···H4^vi	3.304	H4···H4^iv	2.887
C3···H5^v	3.173	H4···H5^ix	2.474
C3···H6^v	3.071	H5···C3^xiv	3.173
C4···H2^vii	3.558	H5···C4ⁱⁱⁱ	3.549
C4···H3^vi	3.531	H5···C4^iv	3.572
C4···H4^vi	3.286	H5···C4^xiv	3.000
C4···H4^iv	3.556	H5···C6^ix	3.200
C4···H5ⁱⁱ	3.549	H5···C7^ix	3.406
C4···H5^iv	3.572	H5···H2^viii	3.345
C4···H5^v	3.000	H5···H2^xiv	3.114
C4···H6^v	3.288	H5···H3^iv	3.098
C5···H2^viii	3.500	H5···H3^xiv	2.834
C5···H4^iv	3.380	H5···H4^ix	2.474
C5···H6^v	3.523	H5···H5^ix	2.911
C6···H2ⁱⁱⁱ	3.523	H6···C1ⁱⁱⁱ	3.425
C6···H2^vii	3.589	H6···C1^xiv	3.368
C6···H2^viii	3.226	H6···C2^xiv	3.130
C6···H3^vii	3.320	H6···C3^xiv	3.071
C6···H3^iv	3.570	H6···C4^xiv	3.288
C6···H4^iv	3.070	H6···C5^xiv	3.523
C6···H5^ix	3.200	H6···C10^xiv	3.551
C7···H2^viii	2.968	H6···C11ⁱⁱⁱ	3.568
C7···H3^iv	3.392	H6···C13^x	3.401
C7···H4^ix	3.379	H6···H1^viii	2.989
C7···H5^ix	3.406	H6···H1^xiv	3.546
C8···H1^viii	3.064	H6···H2^viii	3.357
C8···H2^viii	2.976	H6···H2^xiv	3.427
C8···H9ⁱⁱⁱ	3.492	H6···H9ⁱⁱⁱ	3.049
C8···H12^x	3.211	H6···H12^x	2.414
C9···H1ⁱⁱⁱ	3.444	H7···C12^x	3.490
C9···H1^viii	2.982	H7···H1^viii	2.855
C9···H2^viii	3.249	H7···H8ⁱⁱⁱ	3.170
C9···H8ⁱⁱⁱ	3.434	H7···H9ⁱⁱⁱ	3.465
C9···H12^x	3.532	H7···H10^x	3.124
C10···H1ⁱⁱⁱ	3.535	H7···H(11)^x	3.171
C10···H2^viii	3.499	H7···H12^x	3.075
C10···H6^v	3.551	H7···H13^xi	3.581
C11···H6ⁱⁱ	3.568	H8···C9ⁱⁱ	3.434
C11···H10^xi	3.495	H8···H7ⁱⁱ	3.170
C11···H12^xi	3.499	H8···H10^xi	3.169
C11···H13^xi	3.580	H8···H(11)^xiii	2.892
C12···H7^xi	3.490	H8···H13ⁱⁱ	3.302
C12···H9^x	3.466	H9···C8ⁱⁱ	3.492
C12···H10^xi	3.496	H9···C12^xi	3.466
C12···H10^x	3.543	H9···C13^xi	2.976
C13···H6^xi	3.401	H9···H6ⁱⁱ	3.049
C13···H9^x	2.976	H9···H7ⁱⁱ	3.465
C13···H10^x	3.458	H9···H10^xi	2.941
H1···C8^xii	3.064	H9···H12^xi	2.576
H1···C9ⁱⁱ	3.444	H9···H13^xi	2.648
H1···C9^xii	2.982	H10···C11^x	3.495
H1···C10ⁱⁱ	3.535	H10···C12^xi	3.543
H1···H6^xii	2.989	H10···C12^x	3.496
H1···H6^v	3.546	H10···C13^xi	3.458
H1···H7^xii	2.855	H10···H7^xi	3.124
H1···H(11)^xiii	3.452	H10···H8^x	3.169
H1···H12^xiii	3.500	H10···H9^x	2.941
H2···C4^vi	3.558	H10···H10^xi	3.017
H2···C5^xii	3.500	H10···H10^x	3.017
H2···C6ⁱⁱ	3.523	H10···H(11)^x	3.109
H2···C6^vi	3.589	H10···H13^xi	2.721
H2···C6^xii	3.226	H(11)···H1^xiii	3.452
H2···C7^xii	2.968	H(11)···H7^xi	3.171
H2···C8^xii	2.976	H(11)···H8^xiii	2.892
H2···C9^xii	3.249	H(11)···H10^xi	3.109
H2···C10^xii	3.499	H(11)···H(11)^xiii	3.293
H2···H3^vi	2.684	H(11)···H13ⁱⁱ	2.717
H2···H4ⁱⁱ	3.582	H12···C8^xi	3.211
H2···H4^vi	2.723	H12···C9^xi	3.532
H2···H5^xii	3.345	H12···C11^x	3.499
H2···H5^v	3.114	H12···H1^xiii	3.500
H2···H6^xii	3.357	H12···H6^xi	2.414
H2···H6^v	3.427	H12···H7^xi	3.075
H3···C3^vii	3.316	H12···H9^x	2.576
H3···C4^vii	3.531	H13···C11^x	3.580
H3···C6^vi	3.320	H13···H7^x	3.581
H3···C6^iv	3.570	H13···H8ⁱⁱⁱ	3.302
H3···C7^iv	3.392	H13···H9^x	2.648
H3···H2^vii	2.684	H13···H10^x	2.721
H3···H3^vi	3.094	H13···H(11)ⁱⁱⁱ	2.717

C11—N1—C12	110.5 (2)	C3—C4—H3	119.6
C11—N1—C13ⁱ	110.5 (2)	C5—C4—H3	119.6
C12—N1—C13ⁱ	108.8 (2)	C5—C6—H4	119.3
C2—C1—C10	119.5 (2)	C7—C6—H4	119.3
C2—C1—C11	119.6 (3)	C6—C7—H5	120.0
C10—C1—C11	120.8 (2)	C8—C7—H5	120.0
C1—C2—C3	121.9 (3)	C7—C8—H6	119.8
C2—C3—C4	119.6 (3)	C9—C8—H6	119.8
C3—C4—C5	120.7 (3)	C8—C9—H7	119.5
C4—C5—C6	121.4 (3)	C10—C9—H7	119.5
C4—C5—C10	119.6 (3)	N1—C11—H8	108.8
C6—C5—C10	118.9 (3)	N1—C11—H9	108.8
C5—C6—C7	121.4 (3)	C1—C11—H8	108.8
C6—C7—C8	120.0 (3)	C1—C11—H9	108.8
C7—C8—C9	120.3 (3)	H8—C11—H9	107.7
C8—C9—C10	121.0 (3)	N1—C12—H10	109.5
C1—C10—C5	118.5 (3)	N1—C12—H(11)	109.5
C1—C10—C9	123.2 (2)	C13—C12—H10	109.5
C5—C10—C9	118.2 (3)	C13—C12—H(11)	109.5
N1—C11—C1	114.0 (2)	H10—C12—H(11)	108.1
N1—C12—C13	110.8 (2)	N1ⁱ—C13—H12	109.6
N1ⁱ—C13—C12	110.5 (2)	N1ⁱ—C13—H13	109.6
C1—C2—H1	119.0	C12—C13—H12	109.6
C3—C2—H1	119.0	C12—C13—H13	109.5
C2—C3—H2	120.2	H12—C13—H13	108.1
C4—C3—H2	120.2

C11—N1—C12—C13	−179.8 (3)	C2—C3—C4—C5	−2.2 (6)
C12—N1—C11—C1	−175.8 (3)	C3—C4—C5—C6	179.4 (3)
C11—N1—C13ⁱ—C12ⁱ	179.6 (2)	C3—C4—C5—C10	0.1 (4)
C13ⁱ—N1—C11—C1	63.7 (3)	C4—C5—C6—C7	179.8 (4)
C12—N1—C13ⁱ—C12ⁱ	58.1 (3)	C4—C5—C10—C1	1.7 (5)
C13ⁱ—N1—C12—C13	−58.3 (3)	C4—C5—C10—C9	−179.0 (3)
C2—C1—C10—C5	−1.3 (5)	C6—C5—C10—C1	−177.6 (3)
C2—C1—C10—C9	179.4 (3)	C6—C5—C10—C9	1.7 (5)
C10—C1—C2—C3	−0.8 (6)	C10—C5—C6—C7	−1.0 (6)
C2—C1—C11—N1	−109.9 (4)	C5—C6—C7—C8	0.1 (4)
C11—C1—C2—C3	−178.6 (3)	C6—C7—C8—C9	−0.0 (5)
C10—C1—C11—N1	72.3 (4)	C7—C8—C9—C10	0.8 (6)
C11—C1—C10—C5	176.5 (3)	C8—C9—C10—C1	177.6 (3)
C11—C1—C10—C9	−2.8 (5)	C8—C9—C10—C5	−1.7 (5)
C1—C2—C3—C4	2.6 (6)	N1—C12—C13—N1ⁱ	59.3 (3)

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+2, −y+2, −z+1; (v) x+1/2, −y+5/2, z; (vi) −x+5/2, y−1/2, −z+1; (vii) −x+5/2, y+1/2, −z+1; (viii) x−1/2, −y+3/2, z; (ix) −x+2, −y+3, −z+1; (x) −x+3/2, y+1/2, −z; (xi) −x+3/2, y−1/2, −z; (xii) x+1/2, −y+3/2, z; (xiii) −x+2, −y+1, −z; (xiv) x−1/2, −y+5/2, z.

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1,4-Bis(1-naphthyl­meth­yl)piperazine

Supporting information

Key indicators

checkCIF/PLATON results

1,4-Bis(1-naphthylmethyl)piperazine