(1R,2R)-N,N′-Bis(2-pyridylmethyl­ene)cyclo­hexane-1,2-diamine

Liu, B.; Zhang, M.-J.; Cui, J.; Zhu, J.

doi:10.1107/S1600536806043388

(1R,2R)-N,N'-Bis(2-pyridylmethylene)cyclohexane-1,2-diamine

In the molecule of the title compound, C₁₈H₂₀N₄, the cyclohexane ring has a chair conformation. The dihedral angle between the two planar pyridine rings is 68.19 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043388/hk2140sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043388/hk2140Isup2.hkl Contains datablock I

CCDC reference: 629920

checkCIF report

Key indicators

Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.097
Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



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           27.88
           From the CIF: _reflns_number_total               2239
           Count of symmetry unique reflns         2243
           Completeness (_total/calc)             99.82%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R

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

   2 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
   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 top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2004); software used to prepare material for publication: CrystalStructure.

(1R,2R)-N,N'-Bis(2-pyridylmethylene)cyclohexane-1,2-diamine top

Crystal data top

C₁₈H₂₀N₄	F(000) = 624
M_r = 292.38	D_x = 1.193 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5109 reflections
a = 8.5865 (18) Å	θ = 1.9–28.0°
b = 8.7487 (18) Å	µ = 0.07 mm⁻¹
c = 21.661 (5) Å	T = 113 K
V = 1627.2 (6) Å³	Block, yellow
Z = 4	0.24 × 0.22 × 0.16 mm

Data collection top

Rigaku Saturn diffractometer	2239 independent reflections
Radiation source: rotating anode	2187 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.048
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω scans	h = −11→9
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→11
T_min = 0.978, T_max = 0.988	l = −28→28
20457 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0487P)² + 0.3527P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2239 reflections	Δρ_max = 0.19 e Å⁻³
201 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (4)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.43996 (17)	0.71366 (16)	0.04279 (6)	0.0235 (3)
N2	0.22884 (17)	0.46445 (16)	0.07296 (6)	0.0234 (3)
N3	0.57189 (18)	0.88405 (17)	0.18254 (6)	0.0263 (3)
N4	−0.12533 (19)	0.54853 (19)	0.15088 (7)	0.0299 (4)
C1	0.4501 (2)	0.56284 (19)	0.01357 (7)	0.0223 (3)
H1	0.5193	0.4950	0.0386	0.027*
C2	0.2869 (2)	0.49372 (19)	0.01022 (7)	0.0218 (3)
H2	0.2155	0.5672	−0.0110	0.026*
C3	0.2890 (2)	0.34281 (19)	−0.02540 (8)	0.0239 (4)
H3A	0.1816	0.3024	−0.0286	0.029*
H3B	0.3526	0.2671	−0.0026	0.029*
C4	0.3562 (2)	0.3648 (2)	−0.09025 (8)	0.0246 (4)
H4A	0.3589	0.2653	−0.1120	0.030*
H4B	0.2886	0.4349	−0.1141	0.030*
C5	0.5202 (2)	0.4305 (2)	−0.08663 (8)	0.0255 (4)
H5A	0.5609	0.4475	−0.1288	0.031*
H5B	0.5897	0.3570	−0.0655	0.031*
C6	0.5184 (2)	0.5820 (2)	−0.05118 (7)	0.0249 (4)
H6A	0.6260	0.6217	−0.0479	0.030*
H6B	0.4558	0.6578	−0.0744	0.030*
C7	0.5091 (2)	0.73287 (19)	0.09390 (8)	0.0235 (3)
H7	0.5649	0.6502	0.1118	0.028*
C8	0.5044 (2)	0.88202 (19)	0.12629 (8)	0.0224 (3)
C9	0.43678 (19)	1.01000 (19)	0.09945 (7)	0.0226 (3)
H9	0.3908	1.0035	0.0596	0.027*
C10	0.4372 (2)	1.1476 (2)	0.13146 (8)	0.0254 (4)
H10	0.3910	1.2366	0.1143	0.030*
C11	0.5072 (2)	1.1510 (2)	0.18938 (8)	0.0268 (4)
H11	0.5106	1.2431	0.2126	0.032*
C12	0.5716 (2)	1.0181 (2)	0.21249 (8)	0.0277 (4)
H12	0.6187	1.0220	0.2521	0.033*
C13	0.0938 (2)	0.51433 (18)	0.08546 (8)	0.0223 (3)
H13	0.0397	0.5718	0.0551	0.027*
C14	0.0172 (2)	0.48635 (19)	0.14571 (7)	0.0227 (3)
C15	0.0855 (2)	0.3996 (2)	0.19206 (8)	0.0280 (4)
H15	0.1871	0.3585	0.1868	0.034*
C16	0.0033 (3)	0.3738 (2)	0.24607 (9)	0.0328 (4)
H16	0.0476	0.3159	0.2787	0.039*
C17	−0.1456 (2)	0.4346 (2)	0.25137 (8)	0.0320 (4)
H17	−0.2066	0.4163	0.2872	0.038*
C18	−0.2031 (2)	0.5221 (2)	0.20350 (8)	0.0328 (4)
H18	−0.3036	0.5662	0.2081	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0246 (7)	0.0207 (6)	0.0252 (7)	0.0005 (6)	0.0007 (6)	−0.0010 (6)
N2	0.0243 (7)	0.0224 (7)	0.0235 (7)	−0.0002 (6)	0.0016 (5)	−0.0005 (6)
N3	0.0293 (8)	0.0279 (7)	0.0217 (7)	0.0020 (7)	0.0002 (6)	0.0019 (6)
N4	0.0279 (8)	0.0349 (9)	0.0268 (7)	0.0048 (7)	0.0041 (6)	0.0003 (6)
C1	0.0227 (8)	0.0197 (7)	0.0244 (7)	0.0023 (6)	−0.0002 (6)	−0.0006 (6)
C2	0.0224 (8)	0.0213 (7)	0.0218 (7)	0.0036 (7)	0.0015 (6)	0.0005 (6)
C3	0.0233 (8)	0.0218 (8)	0.0264 (8)	−0.0014 (7)	0.0020 (7)	−0.0009 (7)
C4	0.0269 (8)	0.0227 (8)	0.0243 (8)	0.0029 (7)	0.0007 (7)	−0.0027 (7)
C5	0.0255 (8)	0.0247 (8)	0.0262 (8)	0.0037 (7)	0.0041 (7)	0.0002 (7)
C6	0.0247 (8)	0.0223 (8)	0.0276 (8)	0.0004 (7)	0.0039 (7)	0.0017 (7)
C7	0.0247 (8)	0.0208 (7)	0.0249 (8)	0.0025 (7)	0.0021 (7)	0.0014 (6)
C8	0.0218 (8)	0.0231 (8)	0.0224 (7)	−0.0003 (7)	0.0027 (7)	0.0000 (6)
C9	0.0211 (8)	0.0237 (8)	0.0230 (7)	0.0003 (7)	0.0006 (7)	0.0010 (7)
C10	0.0254 (8)	0.0246 (8)	0.0262 (8)	0.0032 (7)	0.0022 (7)	0.0007 (7)
C11	0.0285 (9)	0.0253 (8)	0.0267 (8)	−0.0013 (8)	0.0048 (7)	−0.0057 (7)
C12	0.0284 (9)	0.0341 (9)	0.0206 (7)	0.0003 (8)	−0.0002 (7)	−0.0015 (7)
C13	0.0255 (8)	0.0174 (7)	0.0240 (7)	−0.0002 (7)	0.0014 (7)	−0.0015 (6)
C14	0.0240 (8)	0.0205 (7)	0.0235 (7)	−0.0021 (7)	0.0006 (6)	−0.0040 (6)
C15	0.0263 (8)	0.0307 (9)	0.0272 (8)	0.0030 (8)	−0.0002 (7)	−0.0019 (7)
C16	0.0370 (9)	0.0374 (10)	0.0239 (8)	0.0047 (9)	0.0001 (7)	0.0018 (7)
C17	0.0320 (9)	0.0409 (11)	0.0229 (8)	−0.0023 (8)	0.0047 (7)	−0.0023 (8)
C18	0.0266 (9)	0.0436 (11)	0.0281 (9)	0.0046 (9)	0.0053 (7)	−0.0025 (8)

Geometric parameters (Å, º) top

N1—C7	1.267 (2)	C6—H6A	0.9900
N1—C1	1.466 (2)	C6—H6B	0.9900
N2—C13	1.268 (2)	C7—C8	1.482 (2)
N2—C2	1.470 (2)	C7—H7	0.9500
N3—C12	1.341 (2)	C8—C9	1.389 (2)
N3—C8	1.349 (2)	C9—C10	1.389 (2)
N4—C18	1.341 (2)	C9—H9	0.9500
N4—C14	1.344 (2)	C10—C11	1.391 (2)
C1—C2	1.528 (2)	C10—H10	0.9500
C1—C6	1.529 (2)	C11—C12	1.381 (3)
C1—H1	1.0000	C11—H11	0.9500
C2—C3	1.529 (2)	C12—H12	0.9500
C2—H2	1.0000	C13—C14	1.482 (2)
C3—C4	1.531 (2)	C13—H13	0.9500
C3—H3A	0.9900	C14—C15	1.389 (2)
C3—H3B	0.9900	C15—C16	1.385 (3)
C4—C5	1.523 (3)	C15—H15	0.9500
C4—H4A	0.9900	C16—C17	1.389 (3)
C4—H4B	0.9900	C16—H16	0.9500
C5—C6	1.532 (2)	C17—C18	1.380 (3)
C5—H5A	0.9900	C17—H17	0.9500
C5—H5B	0.9900	C18—H18	0.9500

C7—N1—C1	117.95 (14)	C5—C6—H6B	109.3
C13—N2—C2	116.59 (15)	H6A—C6—H6B	108.0
C12—N3—C8	116.59 (15)	N1—C7—C8	121.17 (15)
C18—N4—C14	117.04 (16)	N1—C7—H7	119.4
N1—C1—C2	108.80 (13)	C8—C7—H7	119.4
N1—C1—C6	108.66 (13)	N3—C8—C9	123.16 (15)
C2—C1—C6	110.58 (14)	N3—C8—C7	115.31 (14)
N1—C1—H1	109.6	C9—C8—C7	121.53 (15)
C2—C1—H1	109.6	C8—C9—C10	119.24 (15)
C6—C1—H1	109.6	C8—C9—H9	120.4
N2—C2—C1	109.64 (13)	C10—C9—H9	120.4
N2—C2—C3	108.66 (13)	C9—C10—C11	118.03 (16)
C1—C2—C3	110.79 (13)	C9—C10—H10	121.0
N2—C2—H2	109.2	C11—C10—H10	121.0
C1—C2—H2	109.2	C12—C11—C10	118.78 (16)
C3—C2—H2	109.2	C12—C11—H11	120.6
C2—C3—C4	111.04 (14)	C10—C11—H11	120.6
C2—C3—H3A	109.4	N3—C12—C11	124.19 (15)
C4—C3—H3A	109.4	N3—C12—H12	117.9
C2—C3—H3B	109.4	C11—C12—H12	117.9
C4—C3—H3B	109.4	N2—C13—C14	122.49 (16)
H3A—C3—H3B	108.0	N2—C13—H13	118.8
C5—C4—C3	110.42 (14)	C14—C13—H13	118.8
C5—C4—H4A	109.6	N4—C14—C15	123.09 (16)
C3—C4—H4A	109.6	N4—C14—C13	114.25 (15)
C5—C4—H4B	109.6	C15—C14—C13	122.63 (16)
C3—C4—H4B	109.6	C16—C15—C14	118.95 (17)
H4A—C4—H4B	108.1	C16—C15—H15	120.5
C4—C5—C6	110.08 (14)	C14—C15—H15	120.5
C4—C5—H5A	109.6	C15—C16—C17	118.47 (18)
C6—C5—H5A	109.6	C15—C16—H16	120.8
C4—C5—H5B	109.6	C17—C16—H16	120.8
C6—C5—H5B	109.6	C18—C17—C16	118.66 (17)
H5A—C5—H5B	108.2	C18—C17—H17	120.7
C1—C6—C5	111.63 (14)	C16—C17—H17	120.7
C1—C6—H6A	109.3	N4—C18—C17	123.76 (18)
C5—C6—H6A	109.3	N4—C18—H18	118.1
C1—C6—H6B	109.3	C17—C18—H18	118.1

C7—N1—C1—C2	116.45 (17)	N1—C7—C8—C9	−6.0 (3)
C7—N1—C1—C6	−123.09 (16)	N3—C8—C9—C10	−0.2 (3)
C13—N2—C2—C1	130.04 (15)	C7—C8—C9—C10	−179.21 (15)
C13—N2—C2—C3	−108.75 (17)	C8—C9—C10—C11	0.5 (3)
N1—C1—C2—N2	−65.43 (16)	C9—C10—C11—C12	−0.5 (3)
C6—C1—C2—N2	175.31 (14)	C8—N3—C12—C11	0.1 (3)
N1—C1—C2—C3	174.65 (12)	C10—C11—C12—N3	0.2 (3)
C6—C1—C2—C3	55.39 (17)	C2—N2—C13—C14	176.78 (15)
N2—C2—C3—C4	−177.18 (14)	C18—N4—C14—C15	−0.8 (3)
C1—C2—C3—C4	−56.68 (18)	C18—N4—C14—C13	177.50 (16)
C2—C3—C4—C5	57.78 (18)	N2—C13—C14—N4	179.64 (16)
C3—C4—C5—C6	−57.35 (18)	N2—C13—C14—C15	−2.1 (3)
N1—C1—C6—C5	−175.34 (14)	N4—C14—C15—C16	0.7 (3)
C2—C1—C6—C5	−56.00 (18)	C13—C14—C15—C16	−177.40 (16)
C4—C5—C6—C1	57.02 (18)	C14—C15—C16—C17	0.8 (3)
C1—N1—C7—C8	179.95 (15)	C15—C16—C17—C18	−2.1 (3)
C12—N3—C8—C9	−0.1 (2)	C14—N4—C18—C17	−0.7 (3)
C12—N3—C8—C7	178.97 (15)	C16—C17—C18—N4	2.1 (3)
N1—C7—C8—N3	174.87 (15)

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(1R,2R)-N,N'-Bis(2-pyridylmethyl­ene)cyclo­hexane-1,2-diamine

Supporting information

Key indicators

checkCIF/PLATON results

(1R,2R)-N,N'-Bis(2-pyridylmethylene)cyclohexane-1,2-diamine