1,1′,3,3′-Tetra­benz­yl-2,2′-biimidazolidine

The title compound, C₃₄H₃₈N₄, possesses C_i symmetry. The supramolecular structure is achieved by intra­molecular C—H...N and weak inter­molecular C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.140
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C3      ..       6.64 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  CG1     ..       3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  CG2     ..       3.10 Ang.

   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
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

1,1',3,3'-Tetrabenzyl-2,2'-biimidazolidine

Crystal data

C34H38N4	F(000) = 540
Mr = 502.68	Dx = 1.157 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 5.8384 (1) Å	θ = 20–25°
b = 9.6253 (2) Å	µ = 0.07 mm^−1
c = 25.7216 (4) Å	T = 293 K
β = 93.421 (1)°	Block, colorless
V = 1442.88 (4) Å^3	0.15 × 0.1 × 0.09 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	2262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 27.5°, θmin = 4.2°
Detector resolution: 9 pixels mm^-1	h = −7→7
φ and ω scans	k = −12→8
4969 measured reflections	l = −33→33
3185 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.1647P] where P = (Fo^2 + 2Fc^2)/3
3185 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Experimental. Background measurement: Moving crystal and moving counter at the beginning and end of scan, each for 25% of total scan area. Crystal mounted on a glass fiber.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1	1.04063 (19)	0.40326 (11)	0.06374 (4)	0.0564 (4)
N2	0.88401 (19)	0.32282 (10)	−0.01848 (4)	0.0560 (4)
C1	1.0966 (3)	0.25582 (15)	0.05534 (5)	0.0726 (6)
C2	0.9154 (3)	0.20451 (15)	0.01646 (6)	0.0749 (6)
C3	0.9255 (2)	0.44887 (13)	0.01398 (5)	0.0544 (4)
C4	0.6618 (2)	0.32237 (15)	−0.04776 (6)	0.0662 (5)
C5	0.6365 (2)	0.20049 (14)	−0.08443 (5)	0.0602 (5)
C6	0.4453 (3)	0.11588 (18)	−0.08482 (6)	0.0763 (6)
C7	0.4219 (3)	0.0047 (2)	−0.11832 (6)	0.0833 (6)
C8	0.5887 (3)	−0.02533 (16)	−0.15198 (6)	0.0729 (5)
C9	0.7787 (3)	0.05820 (16)	−0.15233 (6)	0.0742 (5)
C10	0.8016 (3)	0.17010 (16)	−0.11901 (7)	0.0721 (6)
C11	0.8997 (3)	0.42454 (17)	0.10822 (5)	0.0665 (5)
C12	1.0251 (3)	0.38645 (15)	0.15938 (5)	0.0630 (5)
C13	0.9354 (3)	0.29056 (19)	0.19243 (6)	0.0805 (6)
C14	1.0523 (4)	0.2546 (2)	0.23927 (6)	0.0961 (8)
C15	1.2567 (4)	0.3158 (2)	0.25372 (7)	0.0941 (8)
C16	1.3470 (3)	0.4111 (2)	0.22160 (7)	0.0909 (7)
C17	1.2336 (3)	0.44596 (19)	0.17477 (6)	0.0787 (6)
H1A	1.24763	0.24666	0.04191	0.0871*
H1B	1.09343	0.20399	0.08763	0.0871*
H2A	0.77479	0.18235	0.03296	0.0898*
H2B	0.96681	0.12316	−0.00181	0.0898*
H3A	0.77860	0.49270	0.02062	0.0653*
H4A	0.54068	0.31920	−0.02357	0.0794*
H4B	0.64474	0.40789	−0.06756	0.0794*
H6	0.33093	0.13429	−0.06212	0.0915*
H7	0.29150	−0.05069	−0.11817	0.1000*
H8	0.57313	−0.10134	−0.17423	0.0874*
H9	0.89248	0.03932	−0.17513	0.0890*
H10	0.93085	0.22632	−0.11982	0.0865*
H11A	0.85367	0.52127	0.10934	0.0798*
H11B	0.76183	0.36862	0.10358	0.0798*
H13	0.79470	0.24927	0.18330	0.0966*
H14	0.99062	0.18853	0.26079	0.1153*
H15	1.33380	0.29273	0.28521	0.1128*
H16	1.48642	0.45318	0.23131	0.1091*
H17	1.29869	0.51063	0.15320	0.0945*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0627 (7)	0.0519 (6)	0.0551 (6)	0.0071 (5)	0.0086 (5)	0.0047 (5)
N2	0.0633 (7)	0.0433 (6)	0.0614 (6)	0.0053 (5)	0.0033 (5)	0.0016 (4)
C1	0.0992 (12)	0.0601 (9)	0.0592 (8)	0.0264 (8)	0.0110 (8)	0.0089 (7)
C2	0.1163 (13)	0.0462 (8)	0.0625 (8)	0.0101 (8)	0.0080 (8)	0.0036 (6)
C3	0.0552 (7)	0.0480 (7)	0.0607 (7)	0.0096 (5)	0.0097 (5)	0.0031 (5)
C4	0.0560 (8)	0.0567 (8)	0.0860 (10)	0.0010 (6)	0.0052 (7)	−0.0006 (7)
C5	0.0584 (8)	0.0538 (8)	0.0678 (8)	−0.0040 (6)	−0.0007 (6)	0.0066 (6)
C6	0.0707 (9)	0.0895 (11)	0.0692 (9)	−0.0246 (8)	0.0084 (7)	−0.0021 (8)
C7	0.0856 (12)	0.0915 (12)	0.0722 (9)	−0.0380 (9)	−0.0012 (8)	−0.0010 (9)
C8	0.0903 (11)	0.0638 (9)	0.0625 (8)	−0.0098 (8)	−0.0119 (8)	0.0036 (7)
C9	0.0763 (10)	0.0680 (9)	0.0789 (9)	0.0006 (8)	0.0101 (8)	−0.0020 (8)
C10	0.0632 (9)	0.0599 (9)	0.0941 (11)	−0.0099 (7)	0.0125 (8)	−0.0017 (7)
C11	0.0654 (9)	0.0734 (9)	0.0614 (8)	0.0049 (7)	0.0098 (7)	−0.0069 (7)
C12	0.0700 (9)	0.0656 (8)	0.0541 (7)	0.0003 (7)	0.0102 (6)	−0.0130 (6)
C13	0.0947 (12)	0.0903 (11)	0.0577 (8)	−0.0233 (9)	0.0140 (8)	−0.0130 (8)
C14	0.1421 (18)	0.0925 (13)	0.0549 (9)	−0.0161 (12)	0.0165 (10)	−0.0016 (9)
C15	0.1221 (16)	0.1011 (14)	0.0574 (9)	0.0053 (12)	−0.0078 (9)	−0.0134 (9)
C16	0.0903 (12)	0.1072 (14)	0.0737 (10)	−0.0071 (10)	−0.0080 (9)	−0.0189 (10)
C17	0.0827 (11)	0.0830 (11)	0.0704 (9)	−0.0127 (9)	0.0040 (8)	−0.0059 (8)

Geometric parameters (Å, º)

N1—C1	1.4751 (18)	C16—C17	1.381 (2)
N1—C3	1.4765 (16)	C1—H1A	0.9700
N1—C11	1.4630 (18)	C1—H1B	0.9700
N2—C2	1.4555 (18)	C2—H2A	0.9701
N2—C3	1.4845 (16)	C2—H2B	0.9700
N2—C4	1.4607 (17)	C3—H3A	0.9799
C1—C2	1.496 (2)	C4—H4A	0.9699
C3—C3^i	1.5223 (17)	C4—H4B	0.9700
C4—C5	1.507 (2)	C6—H6	0.9299
C5—C6	1.381 (2)	C7—H7	0.9296
C5—C10	1.381 (2)	C8—H8	0.9300
C6—C7	1.376 (2)	C9—H9	0.9299
C7—C8	1.372 (2)	C10—H10	0.9298
C8—C9	1.370 (2)	C11—H11A	0.9700
C9—C10	1.378 (2)	C11—H11B	0.9698
C11—C12	1.512 (2)	C13—H13	0.9300
C12—C13	1.379 (2)	C14—H14	0.9297
C12—C17	1.382 (2)	C15—H15	0.9298
C13—C14	1.392 (2)	C16—H16	0.9299
C14—C15	1.362 (3)	C17—H17	0.9300
C15—C16	1.362 (3)
N1···N2^i	2.9260 (14)	H2B···H2B^iii	2.4033
N1···C4^i	3.2011 (17)	H3A···H4A	2.4129
N2···N1^i	2.9260 (14)	H3A···H4B	2.4920
N1···H17	2.8669	H3A···H11A	2.3143
N1···H4B^i	2.5820	H3A···H11B	2.4524
N2···H10	2.7959	H4A···H1A^vi	2.5682
C2···C10	3.524 (2)	H4A···H2A	2.3410
C4···N1^i	3.2011 (17)	H4A···H3A	2.4129
C10···C2	3.524 (2)	H4A···H6	2.3464
C2···H11B	2.9258	H4B···H3A	2.4920
C5···H2A	3.0836	H4B···N1^i	2.5820
C5···H2B	2.8810	H4B···H17^i	2.3798
C8···H15^ii	3.0904	H6···H4A	2.3464
C8···H1B^iii	2.9622	H7···H2A^v	2.5808
C9···H1B^iii	3.0899	H7···H13^v	2.5715
C11···H2A	3.0895	H8···H13^v	2.5756
C12···H1B	2.5956	H10···N2	2.7959
C13···H1B	3.0181	H11A···H3A	2.3143
H1A···H4A^iv	2.5682	H11B···C2	2.9258
H1B···C12	2.5956	H11B···H1B	2.5539
H1B···C13	3.0181	H11B···H2A	2.5566
H1B···H11B	2.5539	H11B···H3A	2.4524
H1B···C8^iii	2.9622	H11B···H13	2.3482
H1B···C9^iii	3.0899	H13···H11B	2.3482
H2A···C5	3.0836	H13···H7^v	2.5715
H2A···C11	3.0895	H13···H8^v	2.5756
H2A···H4A	2.3410	H15···C8^vii	3.0904
H2A···H11B	2.5566	H17···N1	2.8669
H2A···H7^v	2.5808	H17···H4B^i	2.3798
H2B···C5	2.8810
C1—N1—C3	104.62 (10)	C1—C2—H2A	111.31
C1—N1—C11	112.90 (11)	C1—C2—H2B	111.32
C3—N1—C11	112.84 (11)	H2A—C2—H2B	109.20
C2—N2—C3	106.37 (10)	N1—C3—H3A	109.56
C2—N2—C4	113.03 (11)	N2—C3—H3A	109.56
C3—N2—C4	113.73 (10)	C3^i—C3—H3A	109.56
N1—C1—C2	105.16 (12)	N2—C4—H4A	109.18
N2—C2—C1	102.27 (11)	N2—C4—H4B	109.17
N1—C3—N2	107.16 (10)	C5—C4—H4A	109.21
N1—C3—C3^i	111.00 (10)	C5—C4—H4B	109.20
N2—C3—C3^i	109.96 (10)	H4A—C4—H4B	107.91
N2—C4—C5	112.08 (10)	C5—C6—H6	119.56
C4—C5—C6	120.83 (12)	C7—C6—H6	119.56
C4—C5—C10	121.45 (12)	C6—C7—H7	119.62
C6—C5—C10	117.72 (13)	C8—C7—H7	119.61
C5—C6—C7	120.88 (15)	C7—C8—H8	120.47
C6—C7—C8	120.76 (16)	C9—C8—H8	120.46
C7—C8—C9	119.07 (15)	C8—C9—H9	119.90
C8—C9—C10	120.20 (16)	C10—C9—H9	119.90
C5—C10—C9	121.36 (15)	C5—C10—H10	119.32
N1—C11—C12	112.39 (13)	C9—C10—H10	119.32
C11—C12—C13	121.11 (15)	N1—C11—H11A	109.11
C11—C12—C17	121.42 (14)	N1—C11—H11B	109.12
C13—C12—C17	117.47 (14)	C12—C11—H11A	109.11
C12—C13—C14	121.01 (17)	C12—C11—H11B	109.13
C13—C14—C15	120.31 (17)	H11A—C11—H11B	107.88
C14—C15—C16	119.36 (17)	C12—C13—H13	119.51
C15—C16—C17	120.67 (17)	C14—C13—H13	119.49
C12—C17—C16	121.17 (16)	C13—C14—H14	119.86
N1—C1—H1A	110.71	C15—C14—H14	119.83
N1—C1—H1B	110.71	C14—C15—H15	120.33
C2—C1—H1A	110.71	C16—C15—H15	120.31
C2—C1—H1B	110.72	C15—C16—H16	119.66
H1A—C1—H1B	108.81	C17—C16—H16	119.66
N2—C2—H2A	111.31	C12—C17—H17	119.40
N2—C2—H2B	111.32	C16—C17—H17	119.43
C3—N1—C1—C2	−29.26 (14)	N2—C4—C5—C6	129.43 (14)
C11—N1—C1—C2	93.80 (13)	N2—C4—C5—C10	−51.15 (18)
C1—N1—C3—N2	9.03 (13)	C4—C5—C6—C7	179.92 (15)
C11—N1—C3—N2	−114.08 (12)	C6—C5—C10—C9	−0.9 (2)
C1—N1—C3—C3^i	−111.06 (12)	C10—C5—C6—C7	0.5 (2)
C11—N1—C3—C3^i	125.84 (12)	C4—C5—C10—C9	179.67 (14)
C3—N1—C11—C12	−176.18 (11)	C5—C6—C7—C8	0.4 (3)
C1—N1—C11—C12	65.45 (16)	C6—C7—C8—C9	−0.8 (3)
C4—N2—C2—C1	−157.97 (12)	C7—C8—C9—C10	0.4 (2)
C3—N2—C2—C1	−32.47 (14)	C8—C9—C10—C5	0.4 (2)
C4—N2—C3—N1	140.17 (10)	N1—C11—C12—C13	−124.08 (16)
C2—N2—C4—C5	−64.61 (15)	N1—C11—C12—C17	55.81 (19)
C2—N2—C3—N1	15.09 (13)	C17—C12—C13—C14	−0.6 (3)
C2—N2—C3—C3^i	135.84 (11)	C11—C12—C13—C14	179.34 (16)
C4—N2—C3—C3^i	−99.09 (12)	C11—C12—C17—C16	179.80 (16)
C3—N2—C4—C5	173.95 (10)	C13—C12—C17—C16	−0.3 (3)
N1—C1—C2—N2	38.44 (14)	C12—C13—C14—C15	1.2 (3)
N2—C3—C3^i—N1^i	61.59 (13)	C13—C14—C15—C16	−0.9 (3)
N2—C3—C3^i—N2^i	−179.98 (13)	C14—C15—C16—C17	0.0 (3)
N1—C3—C3^i—N2^i	−61.59 (13)	C15—C16—C17—C12	0.6 (3)
N1—C3—C3^i—N1^i	179.98 (12)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x−1, −y+1/2, z−1/2; (iii) −x+2, −y, −z; (iv) x+1, y, z; (v) −x+1, −y, −z; (vi) x−1, y, z; (vii) x+1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N1^i	0.97	2.58	3.2011 (17)	122
C8—H8···Cg1^iii	0.93	3.07	3.8140 (18)	139
C15—H15···Cg2^vii	0.93	3.10	3.894 (2)	144

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