A new chiral Schiff base: (R)-N,N′-bis(3,5-di-tert-butyl­salicyl­idene)-5,5′,6,6′,7,7′,8,8′-octa­hydro-1,1′-bi­naphthyl-2,2′-di­amine

Jia, X.; Li, X.; Zhou, Z.

doi:10.1107/S160053680200082X

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A new chiral Schiff base: (R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine

X. Jia, X. Li and Z. Zhou

The synthetic route to and the chemical structure of a new chiral Schiff base, C₅₀H₆₄N₂O₂, derived from (R)-H8-BINAM [(R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine] are reported.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200082X/ww6003sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680200082X/ww6003Isup2.hkl Contains datablock I

CCDC reference: 180802

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.149
Data-to-parameter ratio = 21.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.103

STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    4.000
         From the CIF: _refine_ls_abs_structure_Flack_su    3.000
           Alert C Chirality of atom sites is inverted?

PLAT_030  Alert C Refined Extinction parameter within range ....       2.80 Sigma

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(5)   -   C(6)   =       1.42 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               5130
         Count of symmetry unique reflns         3056
         Completeness (_total/calc)            167.87%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2074
         Fraction of Friedel pairs measured     0.679
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

(R)—N,N'-bis(3,5-di-tert-butylsalicylidene)-5,5',6,6',7,7',8,8'-octahydro- 1,1'-binaphthyl-2,2'-diamine top

Crystal data top

C₅₀H₆₄N₂O₂	D_x = 1.078 Mg m⁻³
M_r = 725.03	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 1782 reflections
a = 10.6183 (11) Å	θ = 1–27.5°
c = 39.629 (6) Å	µ = 0.06 mm⁻¹
V = 4468.1 (9) Å³	T = 294 K
Z = 4	BLOCK, colorless
F(000) = 1576	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker CCD area-detector diffractometer	5130 independent reflections
Radiation source: fine-focus sealed tube	1824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
φ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −10→13
T_min = 0.987, T_max = 0.989	k = −13→13
30648 measured reflections	l = −51→47

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.149	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.18 e Å⁻³
5130 reflections	Δρ_min = −0.19 e Å⁻³
243 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 4 (3)

Special details top

Experimental. ? #Insert any special details here.

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
O1	0.0850 (2)	0.38119 (19)	0.06384 (6)	0.0690 (7)
H1	0.1555	0.3715	0.0558	0.103*
N1	0.2840 (3)	0.2587 (3)	0.04082 (7)	0.0554 (7)
C1	0.4907 (3)	0.1553 (3)	0.03389 (10)	0.0652 (11)
H1A	0.4673	0.0910	0.0486	0.078*
C2	0.6084 (3)	0.1546 (3)	0.01929 (9)	0.0671 (11)
H2A	0.6642	0.0900	0.0245	0.080*
C3	0.6455 (3)	0.2475 (3)	−0.00288 (9)	0.0569 (9)
C4	0.7743 (3)	0.2404 (4)	−0.01874 (10)	0.0766 (11)
H4A	0.8366	0.2665	−0.0023	0.092*
H4B	0.7918	0.1536	−0.0247	0.092*
C5	0.7874 (4)	0.3203 (5)	−0.04942 (13)	0.1135 (18)
H5A	0.8764	0.3312	−0.0542	0.136*
H5B	0.7506	0.2758	−0.0684	0.136*
C6	0.7307 (4)	0.4412 (4)	−0.04718 (11)	0.0950 (15)
H6A	0.7382	0.4822	−0.0690	0.114*
H6B	0.7779	0.4910	−0.0310	0.114*
C7	0.5935 (3)	0.4425 (3)	−0.03690 (9)	0.0640 (11)
H7A	0.5420	0.4289	−0.0568	0.077*
H7B	0.5730	0.5250	−0.0280	0.077*
C8	0.5606 (3)	0.3439 (3)	−0.01075 (8)	0.0453 (8)
C9	0.4428 (3)	0.3464 (3)	0.00448 (8)	0.0412 (8)
C10	0.4078 (3)	0.2510 (3)	0.02674 (8)	0.0478 (8)
C11	0.2166 (3)	0.1600 (3)	0.04225 (8)	0.0568 (9)
H11A	0.2494	0.0852	0.0338	0.068*
C12	0.0904 (3)	0.1586 (3)	0.05652 (8)	0.0509 (9)
C13	0.0282 (3)	0.2676 (3)	0.06716 (8)	0.0490 (9)
C14	−0.0929 (3)	0.2630 (3)	0.08074 (8)	0.0487 (8)
C15	−0.1441 (3)	0.1443 (3)	0.08488 (8)	0.0546 (9)
H15A	−0.2238	0.1391	0.0945	0.066*
C16	−0.0853 (3)	0.0308 (3)	0.07568 (9)	0.0520 (9)
C17	0.0305 (3)	0.0434 (3)	0.06095 (9)	0.0612 (10)
H17A	0.0713	−0.0289	0.0535	0.073*
C18	−0.1422 (4)	−0.0977 (3)	0.08152 (10)	0.0647 (10)
C19	−0.1655 (4)	−0.1627 (4)	0.04808 (12)	0.1077 (15)
H19A	−0.2242	−0.1141	0.0350	0.162*
H19B	−0.1997	−0.2451	0.0520	0.162*
H19C	−0.0876	−0.1701	0.0360	0.162*
C20	−0.0499 (4)	−0.1781 (4)	0.10204 (11)	0.1015 (13)
H20A	0.0284	−0.1849	0.0901	0.152*
H20B	−0.0848	−0.2606	0.1054	0.152*
H20C	−0.0354	−0.1391	0.1235	0.152*
C21	−0.2666 (4)	−0.0920 (4)	0.10061 (11)	0.1030 (14)
H21A	−0.3263	−0.0436	0.0879	0.154*
H21B	−0.2534	−0.0530	0.1222	0.154*
H21C	−0.2984	−0.1758	0.1038	0.154*
C22	−0.1656 (3)	0.3798 (3)	0.09235 (9)	0.0615 (10)
C23	−0.2991 (3)	0.3482 (4)	0.10496 (12)	0.1047 (16)
H23A	−0.2936	0.2923	0.1240	0.157*
H23B	−0.3458	0.3082	0.0872	0.157*
H23C	−0.3411	0.4243	0.1116	0.157*
C24	−0.0930 (4)	0.4439 (4)	0.12096 (11)	0.0999 (15)
H24A	−0.0833	0.3862	0.1394	0.150*
H24B	−0.1386	0.5168	0.1285	0.150*
H24C	−0.0115	0.4691	0.1130	0.150*
C25	−0.1835 (4)	0.4711 (3)	0.06281 (11)	0.0849 (13)
H25A	−0.2295	0.4300	0.0451	0.127*
H25B	−0.1026	0.4969	0.0545	0.127*
H25C	−0.2295	0.5437	0.0704	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0664 (17)	0.0465 (15)	0.0941 (19)	−0.0043 (12)	0.0164 (14)	−0.0031 (13)
N1	0.0503 (19)	0.0512 (19)	0.0645 (19)	−0.0008 (15)	0.0085 (15)	0.0062 (15)
C1	0.061 (3)	0.051 (2)	0.083 (3)	0.008 (2)	0.009 (2)	0.019 (2)
C2	0.057 (3)	0.060 (2)	0.084 (3)	0.024 (2)	0.007 (2)	0.013 (2)
C3	0.041 (2)	0.060 (2)	0.070 (2)	0.0148 (19)	0.0087 (19)	−0.001 (2)
C4	0.053 (2)	0.087 (3)	0.089 (3)	0.020 (2)	0.023 (2)	0.004 (3)
C5	0.071 (3)	0.127 (4)	0.143 (4)	0.030 (3)	0.054 (3)	0.038 (4)
C6	0.065 (3)	0.097 (4)	0.123 (4)	0.001 (3)	0.039 (3)	0.034 (3)
C7	0.056 (2)	0.056 (2)	0.080 (3)	0.0041 (19)	0.015 (2)	0.007 (2)
C8	0.0380 (19)	0.046 (2)	0.052 (2)	−0.0004 (17)	0.0048 (16)	−0.0008 (17)
C9	0.0339 (18)	0.0359 (17)	0.054 (2)	0.0030 (14)	−0.0004 (15)	−0.0045 (17)
C10	0.040 (2)	0.046 (2)	0.057 (2)	0.0091 (17)	0.0038 (17)	0.0047 (17)
C11	0.061 (2)	0.049 (2)	0.060 (2)	0.008 (2)	0.0087 (19)	0.005 (2)
C12	0.043 (2)	0.044 (2)	0.065 (2)	−0.0004 (17)	0.0133 (17)	−0.0026 (18)
C13	0.054 (2)	0.035 (2)	0.058 (2)	−0.0107 (17)	0.0004 (18)	0.0059 (17)
C14	0.053 (2)	0.042 (2)	0.051 (2)	−0.0012 (18)	0.0073 (17)	−0.0017 (16)
C15	0.045 (2)	0.059 (2)	0.060 (2)	0.000 (2)	0.0093 (17)	0.0044 (18)
C16	0.044 (2)	0.047 (2)	0.065 (2)	−0.0009 (18)	0.0034 (18)	0.0056 (18)
C17	0.065 (3)	0.045 (2)	0.073 (3)	0.0014 (19)	0.006 (2)	0.0004 (19)
C18	0.070 (3)	0.044 (2)	0.079 (3)	−0.008 (2)	0.012 (2)	0.011 (2)
C19	0.125 (4)	0.062 (3)	0.136 (4)	−0.019 (3)	−0.016 (3)	0.000 (3)
C20	0.114 (4)	0.075 (3)	0.115	−0.004 (3)	−0.002 (3)	0.039 (3)
C21	0.113 (4)	0.085 (3)	0.111	−0.035 (3)	0.032 (3)	0.006 (3)
C22	0.066 (2)	0.046 (2)	0.073 (3)	0.0018 (18)	0.018 (2)	−0.006 (2)
C23	0.086 (3)	0.075 (3)	0.153 (4)	0.009 (3)	0.055 (3)	−0.016 (3)
C24	0.118 (4)	0.093 (3)	0.089 (3)	−0.001 (3)	0.002 (3)	−0.035 (3)
C25	0.083 (3)	0.057 (3)	0.114 (4)	0.016 (2)	−0.005 (2)	0.002 (2)

Geometric parameters (Å, º) top

O1—C13	1.355 (3)	C14—C15	1.382 (4)
O1—H1	0.8200	C14—C22	1.531 (4)
N1—C11	1.271 (4)	C15—C16	1.405 (4)
N1—C10	1.430 (4)	C15—H15A	0.9300
C1—C10	1.374 (4)	C16—C17	1.367 (4)
C1—C2	1.378 (4)	C16—C18	1.511 (4)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C3	1.379 (4)	C18—C21	1.523 (5)
C2—H2A	0.9300	C18—C19	1.515 (5)
C3—C8	1.399 (4)	C18—C20	1.533 (5)
C3—C4	1.506 (4)	C19—H19A	0.9600
C4—C5	1.489 (5)	C19—H19B	0.9600
C4—H4A	0.9700	C19—H19C	0.9600
C4—H4B	0.9700	C20—H20A	0.9600
C5—C6	1.421 (5)	C20—H20B	0.9600
C5—H5A	0.9700	C20—H20C	0.9600
C5—H5B	0.9700	C21—H21A	0.9600
C6—C7	1.513 (4)	C21—H21B	0.9600
C6—H6A	0.9700	C21—H21C	0.9600
C6—H6B	0.9700	C22—C24	1.532 (5)
C7—C8	1.514 (4)	C22—C25	1.532 (5)
C7—H7A	0.9700	C22—C23	1.540 (5)
C7—H7B	0.9700	C23—H23A	0.9600
C8—C9	1.389 (4)	C23—H23B	0.9600
C9—C10	1.393 (4)	C23—H23C	0.9600
C9—C9ⁱ	1.491 (5)	C24—H24A	0.9600
C11—C12	1.454 (4)	C24—H24B	0.9600
C11—H11A	0.9300	C24—H24C	0.9600
C12—C17	1.389 (4)	C25—H25A	0.9600
C12—C13	1.398 (4)	C25—H25B	0.9600
C13—C14	1.395 (4)	C25—H25C	0.9600

C13—O1—H1	109.5	C14—C15—H15A	117.4
C11—N1—C10	119.2 (3)	C16—C15—H15A	117.4
C10—C1—C2	119.9 (3)	C17—C16—C15	115.3 (3)
C10—C1—H1A	120.1	C17—C16—C18	120.9 (3)
C2—C1—H1A	120.1	C15—C16—C18	123.8 (3)
C1—C2—C3	121.6 (3)	C16—C17—C12	123.5 (3)
C1—C2—H2A	119.2	C16—C17—H17A	118.3
C3—C2—H2A	119.2	C12—C17—H17A	118.3
C2—C3—C8	118.8 (3)	C16—C18—C21	112.8 (3)
C2—C3—C4	119.3 (3)	C16—C18—C19	110.1 (3)
C8—C3—C4	121.9 (3)	C21—C18—C19	108.1 (4)
C5—C4—C3	113.4 (3)	C16—C18—C20	109.2 (3)
C5—C4—H4A	108.9	C21—C18—C20	108.3 (3)
C3—C4—H4A	108.9	C19—C18—C20	108.4 (3)
C5—C4—H4B	108.9	C18—C19—H19A	109.5
C3—C4—H4B	108.9	C18—C19—H19B	109.5
H4A—C4—H4B	107.7	H19A—C19—H19B	109.5
C6—C5—C4	115.1 (4)	C18—C19—H19C	109.5
C6—C5—H5A	108.5	H19A—C19—H19C	109.5
C4—C5—H5A	108.5	H19B—C19—H19C	109.5
C6—C5—H5B	108.5	C18—C20—H20A	109.5
C4—C5—H5B	108.5	C18—C20—H20B	109.5
H5A—C5—H5B	107.5	H20A—C20—H20B	109.5
C5—C6—C7	115.7 (3)	C18—C20—H20C	109.5
C5—C6—H6A	108.4	H20A—C20—H20C	109.5
C7—C6—H6A	108.4	H20B—C20—H20C	109.5
C5—C6—H6B	108.4	C18—C21—H21A	109.5
C7—C6—H6B	108.4	C18—C21—H21B	109.5
H6A—C6—H6B	107.4	H21A—C21—H21B	109.5
C6—C7—C8	113.6 (3)	C18—C21—H21C	109.5
C6—C7—H7A	108.9	H21A—C21—H21C	109.5
C8—C7—H7A	108.9	H21B—C21—H21C	109.5
C6—C7—H7B	108.9	C24—C22—C14	109.2 (3)
C8—C7—H7B	108.9	C24—C22—C25	110.3 (3)
H7A—C7—H7B	107.7	C14—C22—C25	110.2 (3)
C9—C8—C3	119.8 (3)	C24—C22—C23	108.7 (3)
C9—C8—C7	119.5 (3)	C14—C22—C23	112.7 (3)
C3—C8—C7	120.7 (3)	C25—C22—C23	105.8 (3)
C8—C9—C10	120.1 (3)	C22—C23—H23A	109.5
C8—C9—C9ⁱ	121.9 (3)	C22—C23—H23B	109.5
C10—C9—C9ⁱ	117.8 (2)	H23A—C23—H23B	109.5
C1—C10—C9	119.8 (3)	C22—C23—H23C	109.5
C1—C10—N1	123.4 (3)	H23A—C23—H23C	109.5
C9—C10—N1	116.8 (3)	H23B—C23—H23C	109.5
N1—C11—C12	123.0 (3)	C22—C24—H24A	109.5
N1—C11—H11A	118.5	C22—C24—H24B	109.5
C12—C11—H11A	118.5	H24A—C24—H24B	109.5
C17—C12—C13	118.3 (3)	C22—C24—H24C	109.5
C17—C12—C11	118.7 (3)	H24A—C24—H24C	109.5
C13—C12—C11	123.0 (3)	H24B—C24—H24C	109.5
O1—C13—C12	119.8 (3)	C22—C25—H25A	109.5
O1—C13—C14	118.7 (3)	C22—C25—H25B	109.5
C12—C13—C14	121.5 (3)	H25A—C25—H25B	109.5
C15—C14—C13	116.1 (3)	C22—C25—H25C	109.5
C15—C14—C22	120.3 (3)	H25A—C25—H25C	109.5
C13—C14—C22	123.5 (3)	H25B—C25—H25C	109.5
C14—C15—C16	125.2 (3)

C10—C1—C2—C3	−0.8 (6)	C17—C12—C13—O1	178.6 (3)
C1—C2—C3—C8	−0.4 (6)	C11—C12—C13—O1	1.0 (5)
C1—C2—C3—C4	−178.6 (4)	C17—C12—C13—C14	−2.4 (5)
C2—C3—C4—C5	161.8 (4)	C11—C12—C13—C14	−180.0 (3)
C8—C3—C4—C5	−16.2 (5)	O1—C13—C14—C15	−177.3 (3)
C3—C4—C5—C6	41.3 (6)	C12—C13—C14—C15	3.7 (5)
C4—C5—C6—C7	−53.2 (6)	O1—C13—C14—C22	−0.2 (5)
C5—C6—C7—C8	37.2 (6)	C12—C13—C14—C22	−179.2 (3)
C2—C3—C8—C9	1.8 (5)	C13—C14—C15—C16	−1.8 (5)
C4—C3—C8—C9	179.9 (3)	C22—C14—C15—C16	−179.0 (3)
C2—C3—C8—C7	−175.4 (3)	C14—C15—C16—C17	−1.4 (5)
C4—C3—C8—C7	2.6 (5)	C14—C15—C16—C18	178.1 (3)
C6—C7—C8—C9	170.8 (3)	C15—C16—C17—C12	2.9 (5)
C6—C7—C8—C3	−12.0 (5)	C18—C16—C17—C12	−176.6 (3)
C3—C8—C9—C10	−2.0 (5)	C13—C12—C17—C16	−1.1 (5)
C7—C8—C9—C10	175.3 (3)	C11—C12—C17—C16	176.6 (3)
C3—C8—C9—C9ⁱ	−176.5 (3)	C17—C16—C18—C21	175.6 (4)
C7—C8—C9—C9ⁱ	0.8 (5)	C15—C16—C18—C21	−3.8 (5)
C2—C1—C10—C9	0.6 (6)	C17—C16—C18—C19	−63.6 (4)
C2—C1—C10—N1	180.0 (3)	C15—C16—C18—C19	117.0 (4)
C8—C9—C10—C1	0.8 (5)	C17—C16—C18—C20	55.2 (5)
C9ⁱ—C9—C10—C1	175.5 (3)	C15—C16—C18—C20	−124.2 (4)
C8—C9—C10—N1	−178.7 (3)	C15—C14—C22—C24	115.4 (3)
C9ⁱ—C9—C10—N1	−3.9 (4)	C13—C14—C22—C24	−61.5 (4)
C11—N1—C10—C1	−43.6 (5)	C15—C14—C22—C25	−123.3 (3)
C11—N1—C10—C9	135.8 (3)	C13—C14—C22—C25	59.7 (4)
C10—N1—C11—C12	179.2 (3)	C15—C14—C22—C23	−5.4 (5)
N1—C11—C12—C17	−171.8 (3)	C13—C14—C22—C23	177.6 (3)
N1—C11—C12—C13	5.8 (5)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.643 (3)	148
O1—H1···N1	0.82	1.91	2.643 (3)	148

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