trans-N,N′-Bis(3-methoxy­salicyl­idene)cyclo­hexa­ne-1,2-diamine

The title compound, C₂₂H₂₆N₂O₄, was prepared by reaction of trans-1,2-cyclo­hexa­nediamine and 2-hydr­oxy-3-methoxy­benzaldehyde. The mol­ecular structure is stabilized by intra­molecular O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.061
• wR factor = 0.178
• Data-to-parameter ratio = 24.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        500 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         500 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.19 Ratio

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-N,N'-Bis(3-methoxysalicylidene)-1,2-cyclohexanediamine

Crystal data

C22H26N2O4	Z = 2
Mr = 382.45	F(000) = 408
Triclinic, P1	Dx = 1.234 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.090 (5) Å	Cell parameters from 4027 reflections
b = 10.970 (5) Å	θ = 2.2–30.5°
c = 11.678 (5) Å	µ = 0.09 mm^−1
α = 115.254 (5)°	T = 294 K
β = 112.401 (5)°	Needle, pale yellow
γ = 95.258 (5)°	0.2 × 0.2 × 0.2 mm
V = 1029.7 (8) Å^3

Data collection

Rigaku R-AXIS RAPID-S diffractometer	4115 reflections with I > 2σ(I)
ω scans	Rint = 0.048
Absorption correction: multi-scan (Blessing, 1995)	θmax = 30.5°, θmin = 2.2°
Tmin = 0.973, Tmax = 0.983	h = −14→14
30731 measured reflections	k = −13→15
6285 independent reflections	l = −16→16

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0753P)^2 + 0.1247P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.061	(Δ/σ)max < 0.001
wR(F^2) = 0.179	Δρmax = 0.22 e Å^−3
S = 1.05	Δρmin = −0.20 e Å^−3
6285 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
262 parameters	Extinction coefficient: 0.039 (5)
0 restraints

Special details

Experimental. Uv-vis (λ_max, nm; in EtOH): 422, 327, 295, 280.

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
O3	0.70921 (14)	0.51904 (13)	−0.00418 (13)	0.0671 (3)
H21	0.7306	0.5619	0.0808	0.101*
O1	0.73336 (12)	0.24167 (12)	0.34255 (13)	0.0656 (3)
H7	0.7549	0.3265	0.3698	0.098*
O4	0.66880 (17)	0.36611 (17)	−0.26575 (14)	0.0843 (4)
O2	0.62739 (15)	−0.03197 (13)	0.23482 (16)	0.0780 (4)
C22	0.6475 (3)	0.2882 (4)	−0.4068 (2)	0.1339 (13)
H22A	0.5718	0.3105	−0.468	0.201*
H22B	0.6159	0.1889	−0.4398	0.201*
H22C	0.7404	0.3122	−0.4086	0.201*
H15	0.992 (2)	0.4822 (19)	0.305 (2)	0.069 (5)*
H8	0.479 (2)	0.4559 (19)	0.2324 (19)	0.068 (5)*
N2	0.85450 (15)	0.59426 (13)	0.26929 (13)	0.0531 (3)
C16	0.89708 (17)	0.41847 (15)	0.08687 (16)	0.0495 (3)
N1	0.68645 (15)	0.47760 (14)	0.36649 (14)	0.0546 (3)
C15	0.92030 (18)	0.50197 (16)	0.23275 (16)	0.0527 (4)
C8	0.55124 (19)	0.40773 (17)	0.26931 (17)	0.0543 (4)
C9	0.73833 (18)	0.63031 (16)	0.42458 (16)	0.0532 (4)
H9	0.6616	0.6581	0.3674	0.064*
C21	0.79314 (17)	0.43035 (16)	−0.02469 (16)	0.0508 (3)
C7	0.58586 (17)	0.17926 (17)	0.24817 (16)	0.0523 (3)
C6	0.49247 (17)	0.25594 (17)	0.20876 (16)	0.0532 (4)
C17	0.97957 (19)	0.32407 (17)	0.05808 (17)	0.0585 (4)
H17	1.049	0.3158	0.1322	0.07*
C20	0.77277 (18)	0.34678 (18)	−0.16410 (17)	0.0573 (4)
C14	0.88448 (17)	0.66764 (16)	0.41848 (15)	0.0524 (4)
H14	0.9582	0.6343	0.4713	0.063*
C19	0.85570 (19)	0.25441 (18)	−0.18895 (17)	0.0605 (4)
H19	0.8418	0.1987	−0.2814	0.073*
C2	0.52632 (19)	0.03261 (18)	0.18849 (18)	0.0582 (4)
C18	0.95913 (19)	0.24380 (17)	−0.07802 (18)	0.0625 (4)
H18	1.0151	0.1818	−0.0959	0.075*
C13	0.9491 (2)	0.82687 (17)	0.48640 (18)	0.0615 (4)
H13A	1.0443	0.8475	0.4858	0.074*
H13B	0.8808	0.8598	0.4301	0.074*
C5	0.34032 (19)	0.1848 (2)	0.1090 (2)	0.0673 (4)
H5	0.2775	0.2349	0.0817	0.081*
C10	0.7667 (2)	0.70859 (19)	0.57942 (18)	0.0667 (5)
H10A	0.6731	0.6872	0.5826	0.08*
H10B	0.8374	0.6761	0.6344	0.08*
C3	0.3760 (2)	−0.0339 (2)	0.0916 (2)	0.0677 (5)
H3	0.336	−0.1306	0.0527	0.081*
C12	0.9732 (2)	0.90522 (19)	0.6389 (2)	0.0724 (5)
H12A	1.0072	1.0063	0.6764	0.087*
H12B	1.0508	0.8811	0.698	0.087*
C4	0.2836 (2)	0.0422 (2)	0.0515 (2)	0.0743 (5)
H4	0.1825	−0.004	−0.0148	0.089*
C11	0.8294 (2)	0.86791 (19)	0.6464 (2)	0.0768 (5)
H11A	0.7552	0.9017	0.5963	0.092*
H11B	0.8495	0.9145	0.7456	0.092*
C1	0.5769 (3)	−0.1810 (2)	0.1712 (3)	0.0873 (6)
H1A	0.6581	−0.2128	0.2127	0.131*
H1B	0.5431	−0.2242	0.0701	0.131*
H1C	0.4953	−0.2069	0.1878	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0795 (8)	0.0780 (8)	0.0600 (7)	0.0479 (7)	0.0396 (6)	0.0367 (6)
O1	0.0523 (6)	0.0581 (7)	0.0711 (8)	0.0142 (5)	0.0155 (5)	0.0320 (6)
O4	0.0899 (9)	0.1212 (12)	0.0564 (7)	0.0568 (9)	0.0385 (7)	0.0477 (8)
O2	0.0715 (8)	0.0585 (7)	0.0929 (10)	0.0188 (6)	0.0243 (7)	0.0415 (7)
C22	0.126 (2)	0.229 (4)	0.0592 (12)	0.101 (2)	0.0506 (14)	0.0671 (18)
N2	0.0621 (8)	0.0484 (7)	0.0480 (7)	0.0208 (6)	0.0287 (6)	0.0202 (5)
C16	0.0528 (8)	0.0432 (7)	0.0480 (7)	0.0161 (6)	0.0241 (6)	0.0184 (6)
N1	0.0587 (8)	0.0521 (7)	0.0535 (7)	0.0194 (6)	0.0260 (6)	0.0264 (6)
C15	0.0561 (8)	0.0485 (8)	0.0470 (8)	0.0190 (7)	0.0222 (6)	0.0195 (6)
C8	0.0583 (9)	0.0580 (9)	0.0512 (8)	0.0240 (7)	0.0280 (7)	0.0277 (7)
C9	0.0601 (9)	0.0487 (8)	0.0515 (8)	0.0221 (7)	0.0268 (7)	0.0238 (6)
C21	0.0535 (8)	0.0491 (8)	0.0538 (8)	0.0210 (6)	0.0295 (7)	0.0242 (6)
C7	0.0493 (8)	0.0566 (9)	0.0492 (8)	0.0147 (7)	0.0227 (6)	0.0257 (7)
C6	0.0520 (8)	0.0586 (9)	0.0480 (8)	0.0174 (7)	0.0239 (6)	0.0253 (7)
C17	0.0629 (9)	0.0516 (8)	0.0535 (8)	0.0259 (7)	0.0253 (7)	0.0202 (7)
C20	0.0567 (9)	0.0647 (9)	0.0501 (8)	0.0210 (7)	0.0263 (7)	0.0269 (7)
C14	0.0598 (9)	0.0506 (8)	0.0440 (7)	0.0222 (7)	0.0256 (7)	0.0193 (6)
C19	0.0633 (9)	0.0572 (9)	0.0498 (8)	0.0178 (7)	0.0299 (7)	0.0147 (7)
C2	0.0596 (9)	0.0580 (9)	0.0568 (9)	0.0161 (7)	0.0267 (7)	0.0294 (7)
C18	0.0639 (10)	0.0542 (9)	0.0616 (10)	0.0271 (8)	0.0321 (8)	0.0185 (7)
C13	0.0688 (10)	0.0504 (8)	0.0578 (9)	0.0166 (7)	0.0325 (8)	0.0188 (7)
C5	0.0536 (9)	0.0743 (11)	0.0659 (10)	0.0196 (8)	0.0210 (8)	0.0347 (9)
C10	0.0823 (12)	0.0654 (10)	0.0581 (10)	0.0267 (9)	0.0418 (9)	0.0269 (8)
C3	0.0638 (10)	0.0611 (10)	0.0661 (10)	0.0070 (8)	0.0260 (8)	0.0284 (8)
C12	0.0836 (12)	0.0547 (9)	0.0584 (10)	0.0161 (9)	0.0353 (9)	0.0110 (8)
C4	0.0523 (9)	0.0783 (13)	0.0697 (11)	0.0073 (9)	0.0170 (8)	0.0314 (10)
C11	0.0955 (14)	0.0616 (10)	0.0674 (11)	0.0264 (10)	0.0501 (11)	0.0165 (9)
C1	0.0977 (16)	0.0608 (11)	0.0981 (16)	0.0232 (11)	0.0379 (13)	0.0424 (11)

Geometric parameters (Å, º)

O3—C21	1.3521 (18)	C17—C18	1.366 (2)
O3—H21	0.82	C17—H17	0.93
O1—C7	1.3482 (19)	C20—C19	1.379 (2)
O1—H7	0.82	C14—C13	1.523 (2)
O4—C20	1.364 (2)	C14—H14	0.98
O4—C22	1.409 (3)	C19—C18	1.379 (2)
O2—C2	1.369 (2)	C19—H19	0.93
O2—C1	1.416 (2)	C2—C3	1.378 (2)
C22—H22A	0.96	C18—H18	0.93
C22—H22B	0.96	C13—C12	1.515 (2)
C22—H22C	0.96	C13—H13A	0.97
N2—C15	1.2721 (19)	C13—H13B	0.97
N2—C14	1.4601 (19)	C5—C4	1.368 (3)
C16—C21	1.394 (2)	C5—H5	0.93
C16—C17	1.397 (2)	C10—C11	1.523 (3)
C16—C15	1.456 (2)	C10—H10A	0.97
N1—C8	1.274 (2)	C10—H10B	0.97
N1—C9	1.463 (2)	C3—C4	1.389 (3)
C15—H15	1.006 (19)	C3—H3	0.93
C8—C6	1.456 (2)	C12—C11	1.516 (3)
C8—H8	1.012 (19)	C12—H12A	0.97
C9—C10	1.525 (2)	C12—H12B	0.97
C9—C14	1.530 (2)	C4—H4	0.93
C9—H9	0.98	C11—H11A	0.97
C21—C20	1.404 (2)	C11—H11B	0.97
C7—C6	1.397 (2)	C1—H1A	0.96
C7—C2	1.408 (2)	C1—H1B	0.96
C6—C5	1.402 (2)	C1—H1C	0.96
C21—O3—H21	109.5	C20—C19—C18	120.65 (15)
C7—O1—H7	109.5	C20—C19—H19	119.7
C20—O4—C22	117.29 (17)	C18—C19—H19	119.7
C2—O2—C1	117.76 (15)	O2—C2—C3	125.44 (16)
O4—C22—H22A	109.5	O2—C2—C7	115.08 (14)
O4—C22—H22B	109.5	C3—C2—C7	119.48 (16)
H22A—C22—H22B	109.5	C17—C18—C19	120.22 (15)
O4—C22—H22C	109.5	C17—C18—H18	119.9
H22A—C22—H22C	109.5	C19—C18—H18	119.9
H22B—C22—H22C	109.5	C12—C13—C14	111.56 (14)
C15—N2—C14	117.97 (13)	C12—C13—H13A	109.3
C21—C16—C17	119.45 (14)	C14—C13—H13A	109.3
C21—C16—C15	121.11 (13)	C12—C13—H13B	109.3
C17—C16—C15	119.44 (14)	C14—C13—H13B	109.3
C8—N1—C9	119.23 (13)	H13A—C13—H13B	108
N2—C15—C16	123.52 (14)	C4—C5—C6	120.49 (17)
N2—C15—H15	120.7 (11)	C4—C5—H5	119.8
C16—C15—H15	115.8 (11)	C6—C5—H5	119.8
N1—C8—C6	121.77 (15)	C11—C10—C9	111.31 (14)
N1—C8—H8	121.4 (10)	C11—C10—H10A	109.4
C6—C8—H8	116.8 (10)	C9—C10—H10A	109.4
N1—C9—C10	109.77 (13)	C11—C10—H10B	109.4
N1—C9—C14	109.01 (12)	C9—C10—H10B	109.4
C10—C9—C14	109.55 (13)	H10A—C10—H10B	108
N1—C9—H9	109.5	C2—C3—C4	120.54 (17)
C10—C9—H9	109.5	C2—C3—H3	119.7
C14—C9—H9	109.5	C4—C3—H3	119.7
O3—C21—C16	122.38 (13)	C13—C12—C11	111.19 (15)
O3—C21—C20	118.24 (14)	C13—C12—H12A	109.4
C16—C21—C20	119.38 (14)	C11—C12—H12A	109.4
O1—C7—C6	121.83 (14)	C13—C12—H12B	109.4
O1—C7—C2	118.27 (14)	C11—C12—H12B	109.4
C6—C7—C2	119.90 (15)	H12A—C12—H12B	108
C7—C6—C5	119.17 (16)	C5—C4—C3	120.42 (17)
C7—C6—C8	120.94 (14)	C5—C4—H4	119.8
C5—C6—C8	119.90 (15)	C3—C4—H4	119.8
C18—C17—C16	120.58 (15)	C12—C11—C10	110.97 (15)
C18—C17—H17	119.7	C12—C11—H11A	109.4
C16—C17—H17	119.7	C10—C11—H11A	109.4
O4—C20—C19	125.28 (15)	C12—C11—H11B	109.4
O4—C20—C21	114.99 (14)	C10—C11—H11B	109.4
C19—C20—C21	119.73 (15)	H11A—C11—H11B	108
N2—C14—C13	110.91 (13)	O2—C1—H1A	109.5
N2—C14—C9	108.78 (12)	O2—C1—H1B	109.5
C13—C14—C9	111.29 (12)	H1A—C1—H1B	109.5
N2—C14—H14	108.6	O2—C1—H1C	109.5
C13—C14—H14	108.6	H1A—C1—H1C	109.5
C9—C14—H14	108.6	H1B—C1—H1C	109.5
C14—N2—C15—C16	178.21 (13)	C10—C9—C14—N2	−178.77 (12)
C21—C16—C15—N2	−3.4 (2)	N1—C9—C14—C13	−176.41 (13)
C17—C16—C15—N2	177.10 (16)	C10—C9—C14—C13	−56.29 (17)
C9—N1—C8—C6	−179.13 (13)	O4—C20—C19—C18	179.47 (17)
C8—N1—C9—C10	111.36 (17)	C21—C20—C19—C18	−0.3 (3)
C8—N1—C9—C14	−128.65 (15)	C1—O2—C2—C3	4.7 (3)
C17—C16—C21—O3	179.63 (15)	C1—O2—C2—C7	−175.62 (16)
C15—C16—C21—O3	0.1 (2)	O1—C7—C2—O2	0.4 (2)
C17—C16—C21—C20	0.3 (2)	C6—C7—C2—O2	−179.78 (14)
C15—C16—C21—C20	−179.24 (14)	O1—C7—C2—C3	−179.90 (15)
O1—C7—C6—C5	179.38 (15)	C6—C7—C2—C3	−0.1 (2)
C2—C7—C6—C5	−0.5 (2)	C16—C17—C18—C19	−0.5 (3)
O1—C7—C6—C8	−0.4 (2)	C20—C19—C18—C17	0.6 (3)
C2—C7—C6—C8	179.79 (14)	N2—C14—C13—C12	177.00 (14)
N1—C8—C6—C7	−4.5 (2)	C9—C14—C13—C12	55.75 (19)
N1—C8—C6—C5	175.71 (15)	C7—C6—C5—C4	0.4 (3)
C21—C16—C17—C18	0.0 (2)	C8—C6—C5—C4	−179.86 (16)
C15—C16—C17—C18	179.54 (15)	N1—C9—C10—C11	176.78 (15)
C22—O4—C20—C19	−1.9 (3)	C14—C9—C10—C11	57.12 (19)
C22—O4—C20—C21	178.0 (2)	O2—C2—C3—C4	−179.65 (18)
O3—C21—C20—O4	0.7 (2)	C7—C2—C3—C4	0.7 (3)
C16—C21—C20—O4	−179.94 (14)	C14—C13—C12—C11	−54.9 (2)
O3—C21—C20—C19	−179.50 (15)	C6—C5—C4—C3	0.2 (3)
C16—C21—C20—C19	−0.1 (2)	C2—C3—C4—C5	−0.7 (3)
C15—N2—C14—C13	121.25 (16)	C13—C12—C11—C10	55.4 (2)
C15—N2—C14—C9	−116.03 (16)	C9—C10—C11—C12	−57.1 (2)
N1—C9—C14—N2	61.10 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H7···N1	0.82	1.86	2.590 (3)	147
O3—H21···N2	0.82	1.92	2.644 (2)	147