(R,R)-4,4′-Dimethyl-2,2′-[cyclo­hexane-1,2-diylbis(nitrilomethylidyne)]diphenol

The title compound, C₂₂H₂₆N₂O₂, has been prepared by reaction of 1,2-cyclo­hexa­nediamine and 5-methyl-2-hydroxy­benzaldehyde. The mol­ecular structure is stabilized by intra­molecular O—H...N hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.072
• Data-to-parameter ratio = 11.4

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           28.29
           From the CIF: _reflns_number_total               2782
           Count of symmetry unique reflns         2808
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(R,R)-4,4'-dimethyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenol

Crystal data

C22H26N2O2	F(000) = 752
Mr = 350.45	Dx = 1.172 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6042 reflections
a = 8.9896 (5) Å	θ = 2.2–26,76°
b = 10.3568 (6) Å	µ = 0.08 mm^−1
c = 21.3397 (13) Å	T = 291 K
V = 1986.8 (2) Å^3	Block, yellow
Z = 4	0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer	2782 independent reflections
Radiation source: sealed tube	1636 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.98, Tmax = 0.98	k = −13→13
15010 measured reflections	l = −27→28

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.03P)^2] where P = (Fo^2 + 2Fc^2)/3
2782 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.09 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. ¹H NMR (300 MHz, CDCl₃): δ 13.62 (s, 2H), 8.12 (s, 2H), 6.71–7.18 (m, 6H), 3.20–3.23 (m, 2H), 2.13 (s, 6H), 1.65–1.86 (m, 6H), 1.32–1.42 (m, 2H). IR (KBr, cm^-1): 3476, 2940, 2858, 1627, 1490, 1442, 1270, 1144, 1094, 845, 773.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.34950 (19)	−0.01144 (14)	0.13426 (7)	0.0598 (4)
H1	0.2500	−0.0252	0.1167	0.072*
C2	0.3370 (2)	−0.00267 (16)	0.20529 (7)	0.0735 (5)
H2A	0.4334	0.0195	0.2226	0.088*
H2B	0.2680	0.0658	0.2161	0.088*
C3	0.2840 (2)	−0.12792 (17)	0.23433 (8)	0.0804 (5)
H3A	0.2805	−0.1191	0.2796	0.097*
H3B	0.1845	−0.1475	0.2196	0.097*
C4	0.3881 (3)	−0.23631 (18)	0.21683 (8)	0.0894 (6)
H4A	0.3515	−0.3167	0.2343	0.107*
H4B	0.4857	−0.2197	0.2345	0.107*
C5	0.4009 (2)	−0.24908 (16)	0.14597 (8)	0.0846 (6)
H5A	0.3052	−0.2749	0.1291	0.102*
H5B	0.4720	−0.3165	0.1362	0.102*
C6	0.4498 (2)	−0.12418 (15)	0.11446 (7)	0.0658 (4)
H6	0.5530	−0.1051	0.1260	0.079*
C7	0.36276 (19)	0.15141 (15)	0.05717 (8)	0.0615 (4)
H7	0.2932	0.1027	0.0352	0.074*
C8	0.41624 (18)	0.27170 (15)	0.02970 (7)	0.0591 (4)
C9	0.50631 (19)	0.35618 (15)	0.06385 (8)	0.0640 (4)
C10	0.5464 (2)	0.47346 (16)	0.03786 (9)	0.0777 (5)
H10	0.6029	0.5316	0.0610	0.093*
C11	0.5033 (2)	0.50433 (17)	−0.02178 (10)	0.0795 (5)
H11	0.5309	0.5839	−0.0383	0.095*
C12	0.4199 (2)	0.42080 (19)	−0.05832 (9)	0.0764 (5)
C13	0.37546 (19)	0.30500 (16)	−0.03133 (8)	0.0690 (5)
H13	0.3171	0.2482	−0.0545	0.083*
C14	0.3795 (3)	0.4524 (2)	−0.12530 (9)	0.1083 (7)
H14A	0.4526	0.4162	−0.1530	0.162*
H14B	0.3767	0.5444	−0.1306	0.162*
H14C	0.2836	0.4167	−0.1349	0.162*
C15	0.5353 (2)	−0.08504 (16)	0.01117 (8)	0.0649 (5)
H15	0.6174	−0.0452	0.0293	0.078*
C16	0.52010 (19)	−0.08375 (14)	−0.05668 (7)	0.0594 (4)
C17	0.40703 (19)	−0.15250 (15)	−0.08653 (8)	0.0617 (4)
C18	0.3956 (2)	−0.14769 (19)	−0.15136 (8)	0.0795 (5)
H18	0.3224	−0.1950	−0.1719	0.095*
C19	0.4937 (2)	−0.07207 (18)	−0.18516 (9)	0.0828 (6)
H19	0.4853	−0.0700	−0.2286	0.099*
C20	0.6037 (2)	0.00048 (18)	−0.15695 (8)	0.0765 (5)
C21	0.61598 (19)	−0.00889 (16)	−0.09282 (8)	0.0716 (5)
H21	0.6914	0.0366	−0.0728	0.086*
C22	0.7053 (3)	0.0861 (2)	−0.19511 (10)	0.1149 (8)
H22A	0.6936	0.0666	−0.2388	0.172*
H22B	0.8067	0.0711	−0.1829	0.172*
H22C	0.6803	0.1749	−0.1878	0.172*
N1	0.40813 (15)	0.11076 (12)	0.11022 (6)	0.0617 (4)
N2	0.43905 (17)	−0.13948 (12)	0.04661 (6)	0.0647 (4)
O1	0.55423 (16)	0.32670 (12)	0.12212 (6)	0.0825 (4)
H1B	0.530 (2)	0.2381 (17)	0.1307 (8)	0.099*
O2	0.30682 (13)	−0.22368 (11)	−0.05412 (6)	0.0753 (4)
H2D	0.316 (2)	−0.2051 (15)	−0.0105 (9)	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0650 (10)	0.0588 (10)	0.0556 (9)	−0.0004 (8)	−0.0049 (8)	−0.0020 (7)
C2	0.0895 (13)	0.0728 (11)	0.0582 (10)	0.0017 (10)	0.0001 (9)	−0.0021 (9)
C3	0.1013 (15)	0.0837 (13)	0.0564 (10)	0.0011 (12)	0.0029 (10)	0.0060 (9)
C4	0.1218 (17)	0.0785 (12)	0.0677 (11)	0.0082 (14)	−0.0085 (11)	0.0122 (10)
C5	0.1161 (16)	0.0662 (11)	0.0717 (12)	0.0100 (12)	−0.0005 (11)	0.0044 (9)
C6	0.0695 (11)	0.0703 (10)	0.0575 (9)	0.0029 (9)	−0.0062 (9)	−0.0027 (8)
C7	0.0634 (10)	0.0617 (9)	0.0595 (10)	−0.0014 (8)	−0.0046 (8)	−0.0057 (8)
C8	0.0580 (10)	0.0599 (9)	0.0595 (10)	0.0041 (9)	0.0047 (8)	−0.0018 (8)
C9	0.0641 (11)	0.0640 (10)	0.0638 (10)	0.0010 (9)	0.0104 (9)	−0.0100 (9)
C10	0.0787 (13)	0.0645 (11)	0.0898 (14)	−0.0051 (10)	0.0186 (11)	−0.0105 (10)
C11	0.0725 (14)	0.0637 (11)	0.1022 (15)	0.0060 (10)	0.0265 (12)	0.0078 (11)
C12	0.0690 (12)	0.0831 (12)	0.0771 (12)	0.0166 (11)	0.0151 (10)	0.0191 (10)
C13	0.0661 (11)	0.0767 (11)	0.0642 (11)	0.0038 (9)	−0.0009 (9)	0.0030 (9)
C14	0.1073 (17)	0.1296 (17)	0.0879 (14)	0.0154 (15)	0.0093 (12)	0.0418 (14)
C15	0.0642 (11)	0.0664 (10)	0.0641 (11)	0.0054 (9)	−0.0056 (9)	−0.0100 (8)
C16	0.0596 (11)	0.0596 (9)	0.0592 (9)	0.0048 (9)	−0.0014 (8)	−0.0068 (8)
C17	0.0643 (11)	0.0571 (9)	0.0636 (10)	0.0034 (9)	−0.0027 (9)	−0.0018 (8)
C18	0.0828 (13)	0.0874 (12)	0.0684 (12)	−0.0085 (12)	−0.0163 (10)	−0.0052 (10)
C19	0.0926 (15)	0.0951 (13)	0.0607 (11)	0.0001 (13)	−0.0108 (10)	0.0057 (10)
C20	0.0806 (14)	0.0803 (11)	0.0685 (12)	−0.0024 (11)	0.0009 (10)	0.0029 (9)
C21	0.0690 (12)	0.0795 (11)	0.0662 (11)	−0.0080 (10)	−0.0022 (9)	−0.0085 (9)
C22	0.1202 (19)	0.1328 (18)	0.0917 (15)	−0.0380 (17)	0.0111 (14)	0.0176 (13)
N1	0.0699 (9)	0.0602 (8)	0.0550 (8)	−0.0016 (7)	−0.0029 (7)	−0.0023 (6)
N2	0.0728 (9)	0.0631 (8)	0.0583 (8)	0.0031 (8)	−0.0031 (8)	−0.0062 (6)
O1	0.0967 (9)	0.0858 (8)	0.0650 (7)	−0.0170 (8)	−0.0061 (7)	−0.0107 (7)
O2	0.0798 (8)	0.0720 (7)	0.0741 (7)	−0.0139 (7)	−0.0054 (7)	−0.0001 (6)

Geometric parameters (Å, º)

C1—N1	1.4637 (19)	C11—C12	1.385 (3)
C1—C2	1.523 (2)	C11—H11	0.9300
C1—C6	1.534 (2)	C12—C13	1.389 (2)
C1—H1	0.9800	C12—C14	1.511 (3)
C2—C3	1.514 (2)	C13—H13	0.9300
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—C4	1.509 (3)	C14—H14C	0.9600
C3—H3A	0.9700	C15—N2	1.280 (2)
C3—H3B	0.9700	C15—C16	1.454 (2)
C4—C5	1.522 (2)	C15—H15	0.9300
C4—H4A	0.9700	C16—C21	1.393 (2)
C4—H4B	0.9700	C16—C17	1.395 (2)
C5—C6	1.523 (2)	C17—O2	1.3540 (18)
C5—H5A	0.9700	C17—C18	1.388 (2)
C5—H5B	0.9700	C18—C19	1.383 (2)
C6—N2	1.4597 (19)	C18—H18	0.9300
C6—H6	0.9800	C19—C20	1.380 (2)
C7—N1	1.2749 (19)	C19—H19	0.9300
C7—C8	1.458 (2)	C20—C21	1.376 (2)
C7—H7	0.9300	C20—C22	1.512 (3)
C8—C13	1.396 (2)	C21—H21	0.9300
C8—C9	1.397 (2)	C22—H22A	0.9600
C9—O1	1.3508 (19)	C22—H22B	0.9600
C9—C10	1.383 (2)	C22—H22C	0.9600
C10—C11	1.368 (3)	O1—H1B	0.961 (17)
C10—H10	0.9300	O2—H2D	0.955 (18)
N1—C1—C2	108.89 (13)	C9—C10—H10	119.9
N1—C1—C6	110.48 (12)	C10—C11—C12	122.07 (17)
C2—C1—C6	111.28 (13)	C10—C11—H11	119.0
N1—C1—H1	108.7	C12—C11—H11	119.0
C2—C1—H1	108.7	C11—C12—C13	117.48 (16)
C6—C1—H1	108.7	C11—C12—C14	121.82 (18)
C3—C2—C1	112.30 (14)	C13—C12—C14	120.7 (2)
C3—C2—H2A	109.1	C12—C13—C8	121.64 (17)
C1—C2—H2A	109.1	C12—C13—H13	119.2
C3—C2—H2B	109.1	C8—C13—H13	119.2
C1—C2—H2B	109.1	C12—C14—H14A	109.5
H2A—C2—H2B	107.9	C12—C14—H14B	109.5
C4—C3—C2	109.94 (15)	H14A—C14—H14B	109.5
C4—C3—H3A	109.7	C12—C14—H14C	109.5
C2—C3—H3A	109.7	H14A—C14—H14C	109.5
C4—C3—H3B	109.7	H14B—C14—H14C	109.5
C2—C3—H3B	109.7	N2—C15—C16	121.89 (16)
H3A—C3—H3B	108.2	N2—C15—H15	119.1
C3—C4—C5	110.93 (15)	C16—C15—H15	119.1
C3—C4—H4A	109.5	C21—C16—C17	118.83 (15)
C5—C4—H4A	109.5	C21—C16—C15	119.88 (15)
C3—C4—H4B	109.5	C17—C16—C15	121.24 (16)
C5—C4—H4B	109.5	O2—C17—C18	118.63 (16)
H4A—C4—H4B	108.0	O2—C17—C16	121.97 (14)
C4—C5—C6	112.74 (15)	C18—C17—C16	119.40 (17)
C4—C5—H5A	109.0	C19—C18—C17	119.52 (18)
C6—C5—H5A	109.0	C19—C18—H18	120.2
C4—C5—H5B	109.0	C17—C18—H18	120.2
C6—C5—H5B	109.0	C20—C19—C18	122.53 (17)
H5A—C5—H5B	107.8	C20—C19—H19	118.7
N2—C6—C5	109.07 (14)	C18—C19—H19	118.7
N2—C6—C1	108.48 (13)	C21—C20—C19	116.95 (18)
C5—C6—C1	110.80 (13)	C21—C20—C22	121.90 (19)
N2—C6—H6	109.5	C19—C20—C22	121.15 (18)
C5—C6—H6	109.5	C20—C21—C16	122.69 (17)
C1—C6—H6	109.5	C20—C21—H21	118.7
N1—C7—C8	122.25 (15)	C16—C21—H21	118.7
N1—C7—H7	118.9	C20—C22—H22A	109.5
C8—C7—H7	118.9	C20—C22—H22B	109.5
C13—C8—C9	118.95 (15)	H22A—C22—H22B	109.5
C13—C8—C7	119.96 (15)	C20—C22—H22C	109.5
C9—C8—C7	121.09 (15)	H22A—C22—H22C	109.5
O1—C9—C10	118.98 (16)	H22B—C22—H22C	109.5
O1—C9—C8	121.56 (15)	C7—N1—C1	118.78 (13)
C10—C9—C8	119.46 (16)	C15—N2—C6	119.56 (15)
C11—C10—C9	120.30 (18)	C9—O1—H1B	108.6 (11)
C11—C10—H10	119.9	C17—O2—H2D	109.5 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.961 (17)	1.768 (18)	2.6060 (17)	143.7 (16)
O2—H2D···N2	0.955 (18)	1.783 (19)	2.6065 (17)	142.6 (17)