(S)-(+)-2,2′-Bis(2-hydr­oxy-3-methoxy­benzyl­ideneamino)-1,1′-binaphth­yl

Chai, W.-L.; Bi, W.-Y.; Lü, X.-Q.; Song, J.-R.; Ng, S.W.

doi:10.1107/S1600536807025937

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(S)-(+)-2,2'-Bis(2-hydroxy-3-methoxybenzylideneamino)-1,1'-binaphthyl

W.-L. Chai, W.-Y. Bi, X.-Q. Lü, J.-R. Song and S. W. Ng

In the chiral title compound, C₃₆H₂₈N₂O₄, the two naphthyl systems are twisted by 81.2 (1)° about their linking C-C single bond. The OH group forms an intramolecular hydrogen bond with the imino N acceptor atom. The complete molecule has twofold symmetry and shows extensive disorder of the pendant substituted aromatic ring; the site occupancy ratio is 0.78:0.22.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025937/hb2421sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025937/hb2421Isup2.hkl Contains datablock I

CCDC reference: 654849

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.058
wR factor = 0.203
Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.22 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C3'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         O2
PLAT301_ALERT_3_B Main Residue  Disorder .........................      28.00 Perc.

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.79
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.69 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O2'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C1'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C2'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.12
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H12    ..  H7A'    ..       2.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

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           25.00
           From the CIF: _reflns_number_total               1629
           Count of symmetry unique reflns         1629
           Completeness (_total/calc)            100.00%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        114

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The nickel derivatives of the Schiff bases that are formed by condensing 2,2'-diamino-1,1-binaphthyl with aldehydes are catalysts for enantioselective Diels-Alder reactions (Suga et al., 2003, 2004). The present crystallographic study follows the study on racemic 2,2'-bis(2-hydroxy-3-ethoxybenzylideneamino)-1,1'-binaphthyl, which exists as a dichloromethane solvate (Che et al., 2002). The title compound is a substitutted 1,1'-binaphthyl that lies on a twofold rotation axis; the fused-rings are twisted by 81.2 (1) ° along the naphthyl–naphthyl bond. The hydroxy group forms an internal hydrogen bond with the imino nitrogen, a feature that is common to Schiff bases derived from a substituted salicyaldehyde such as o-vanillin and an amine (Cambridge Structural Database Version 5.28, November 2006).

The structure of the optically active (S)-(+)-2,2'-diamino-1,1'-binaphthyl reactant has not been reported although the R-enantiomer has already been described (in the P4₃2₁2 space group) (Jones et al., 2003). The space group of the S-enantiomer should be that of the present Schiff base, i.e., P4₁2₁2.

Related literature top

For the crystal structure of the racemic modification of the title compound, see Che et al., 2002; for the opposite enantiomer of the starting material, see: Jones et al. (2003).

For related literature, see: Suga et al. (2003, 2004).

Experimental top

(S)-(+)-2,2'-Diamino-1,1'-binaphthyl (0.144 g, 0.5 mmol) and o-vanillin (0.162 g, 1.05 mmol) was heated in ethanol (10 ml) for several hours. The orange compound that resulted was isolated and recrystallized from ethanol to yield orange prisms of (I) in 70% yield. CH&N elemental analysis: calc. for C₃₆H₂₈N₂O₄: C 78.24, H 5.11, N 5.07. Found: C 78.31, H 5.08, N 5.04%.

Structure description top

For the crystal structure of the racemic modification of the title compound, see Che et al., 2002; for the opposite enantiomer of the starting material, see: Jones et al. (2003).

For related literature, see: Suga et al. (2003, 2004).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. View of (I) showing 30% displacement ellipsoids. Hydrogen atoms are drawn as spheres of arbitrary radius; the minor disorder component is not shown. Symmetry code (i): y - 1, 1 + x, 2 - z.

(S)-(+)-2,2'-Bis(2-hydroxy-3-methoxybenzylideneamino)-1,1'-binaphthyl top

Crystal data top

C₃₆H₂₈N₂O₄	D_x = 1.200 Mg m⁻³
M_r = 552.60	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 4468 reflections
Hall symbol: P 4abw 2nw	θ = 2.5–21.0°
a = 11.3285 (6) Å	µ = 0.08 mm⁻¹
c = 23.837 (1) Å	T = 295 K
V = 3059.1 (2) Å³	Prism, orange
Z = 4	0.38 × 0.31 × 0.28 mm
F(000) = 1160

Data collection top

Bruker APEX diffractometer	1190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
φ and ω scans	h = −13→8
15298 measured reflections	k = −13→11
1629 independent reflections	l = −28→28

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.203	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1153P)² + 0.6898P] where P = (F_o² + 2F_c²)/3
1629 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.19 e Å⁻³
114 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₃₆H₂₈N₂O₄	Z = 4
M_r = 552.60	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.08 mm⁻¹
a = 11.3285 (6) Å	T = 295 K
c = 23.837 (1) Å	0.38 × 0.31 × 0.28 mm
V = 3059.1 (2) Å³

Data collection top

Bruker APEX diffractometer	1190 reflections with I > 2σ(I)
15298 measured reflections	R_int = 0.028
1629 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	114 restraints
wR(F²) = 0.203	H-atom parameters constrained
S = 1.10	Δρ_max = 0.19 e Å⁻³
1629 reflections	Δρ_min = −0.18 e Å⁻³
240 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.4176 (3)	0.0978 (3)	1.10647 (12)	0.0838 (10)
H1	0.3736	0.1062	1.0795	0.101*
N1	0.3657 (3)	0.1225 (3)	1.00195 (13)	0.0697 (10)
O2'	0.578 (2)	0.061 (2)	1.1879 (8)	0.132 (12)	0.219 (14)
C1'	0.5305 (9)	0.1015 (11)	1.0912 (10)	0.068 (8)	0.219 (14)
C2'	0.6125 (17)	0.0804 (17)	1.1334 (7)	0.086 (8)	0.219 (14)
C3'	0.7324 (14)	0.080 (3)	1.1210 (8)	0.142 (13)	0.219 (14)
H3'	0.7873	0.0663	1.1493	0.170*	0.219 (14)
C4'	0.7703 (9)	0.102 (3)	1.0665 (9)	0.125 (11)	0.219 (14)
H4'	0.8506	0.1015	1.0582	0.150*	0.219 (14)
C5'	0.6883 (15)	0.123 (2)	1.0243 (7)	0.121 (11)	0.219 (14)
H5'	0.7137	0.1367	0.9878	0.146*	0.219 (14)
C6'	0.5684 (13)	0.1226 (13)	1.0366 (8)	0.098 (10)	0.219 (14)
C7'	0.664 (4)	0.038 (3)	1.2268 (11)	0.128 (12)	0.219 (14)
H7A'	0.6278	0.0207	1.2623	0.193*	0.219 (14)
H7B'	0.7132	0.1067	1.2306	0.193*	0.219 (14)
H7C'	0.7104	−0.02725	1.2148	0.193*	0.219 (14)
O2	0.5688 (8)	0.1093 (10)	1.1871 (3)	0.137 (3)	0.781 (14)
C1	0.5282 (4)	0.1316 (6)	1.0922 (3)	0.086 (3)	0.781 (14)
C2	0.6118 (6)	0.1401 (8)	1.1347 (2)	0.105 (3)	0.781 (14)
C3	0.7258 (5)	0.1773 (10)	1.1223 (2)	0.145 (4)	0.781 (14)
H3	0.7818	0.1830	1.1507	0.174*	0.781 (14)
C4	0.7561 (4)	0.2060 (10)	1.0674 (3)	0.145 (4)	0.781 (14)
H4	0.8324	0.2308	1.0592	0.173*	0.781 (14)
C5	0.6724 (5)	0.1974 (8)	1.0250 (2)	0.119 (4)	0.781 (14)
H5	0.6927	0.2166	0.9883	0.143*	0.781 (14)
C6	0.5585 (4)	0.1602 (6)	1.0374 (3)	0.089 (2)	0.781 (14)
C7	0.6429 (16)	0.1174 (15)	1.2321 (4)	0.236 (8)	0.781 (14)
H7A	0.6017	0.0939	1.2655	0.354*	0.781 (14)
H7B	0.6694	0.1975	1.2360	0.354*	0.781 (14)
H7C	0.7097	0.0667	1.2264	0.354*	0.781 (14)
C8	0.4746 (4)	0.1482 (5)	0.99170 (18)	0.0920 (17)
H8	0.4994	0.1591	0.9549	0.110*
C9	0.1660 (3)	0.1302 (3)	0.97066 (13)	0.0560 (9)
C10	0.2827 (4)	0.1112 (4)	0.95811 (14)	0.0630 (11)
C11	0.3159 (4)	0.0788 (5)	0.90282 (15)	0.0797 (13)
H11	0.3950	0.0651	0.8948	0.096*
C12	0.2355 (4)	0.0674 (5)	0.86193 (16)	0.0824 (14)
H12	0.2598	0.0460	0.8261	0.099*
C13	0.1139 (4)	0.0876 (4)	0.87250 (16)	0.0743 (12)
C14	0.0797 (4)	0.1173 (4)	0.92788 (16)	0.0650 (11)
C15	−0.0424 (4)	0.1352 (6)	0.93804 (19)	0.0926 (16)
H15	−0.0678	0.1550	0.9739	0.111*
C16	−0.1225 (6)	0.1239 (8)	0.8962 (2)	0.127 (3)
H16	−0.2022	0.1361	0.9035	0.153*
C17	−0.0859 (6)	0.0937 (7)	0.8418 (2)	0.125 (3)
H17	−0.1414	0.0857	0.8133	0.150*
C18	0.0296 (5)	0.0762 (6)	0.83076 (19)	0.1031 (19)
H18	0.0530	0.0562	0.7946	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.098 (3)	0.093 (2)	0.0602 (16)	−0.013 (2)	−0.0103 (16)	0.0161 (16)
N1	0.063 (2)	0.096 (3)	0.0502 (16)	0.0047 (18)	0.0033 (15)	−0.0002 (18)
O2'	0.165 (19)	0.128 (18)	0.104 (16)	0.008 (13)	−0.074 (13)	0.034 (11)
C1'	0.073 (17)	0.081 (13)	0.051 (13)	0.020 (11)	−0.011 (12)	0.001 (10)
C2'	0.079 (14)	0.093 (17)	0.087 (15)	0.001 (12)	0.008 (12)	−0.011 (12)
C3'	0.13 (2)	0.18 (2)	0.116 (18)	−0.019 (18)	−0.003 (16)	−0.017 (18)
C4'	0.102 (17)	0.18 (2)	0.090 (15)	0.006 (16)	−0.005 (13)	0.011 (16)
C5'	0.074 (15)	0.19 (2)	0.102 (16)	0.039 (15)	−0.007 (13)	−0.001 (16)
C6'	0.072 (16)	0.16 (2)	0.062 (14)	0.010 (14)	0.015 (13)	0.003 (14)
C7'	0.15 (2)	0.114 (18)	0.126 (18)	−0.002 (15)	−0.071 (16)	0.028 (14)
O2	0.156 (6)	0.182 (8)	0.073 (4)	−0.027 (6)	−0.043 (4)	0.046 (4)
C1	0.083 (6)	0.101 (5)	0.073 (6)	0.011 (4)	−0.012 (5)	−0.006 (4)
C2	0.099 (6)	0.127 (8)	0.088 (5)	−0.001 (5)	−0.027 (4)	−0.003 (5)
C3	0.110 (7)	0.228 (13)	0.097 (6)	0.020 (7)	−0.033 (5)	−0.025 (7)
C4	0.066 (4)	0.230 (13)	0.137 (7)	−0.011 (6)	−0.009 (5)	−0.040 (8)
C5	0.072 (5)	0.205 (10)	0.080 (4)	0.005 (6)	0.004 (4)	−0.037 (5)
C6	0.061 (5)	0.129 (6)	0.076 (5)	0.011 (4)	−0.004 (4)	−0.021 (4)
C7	0.219 (14)	0.363 (19)	0.126 (8)	−0.064 (15)	−0.083 (9)	0.075 (11)
C8	0.069 (3)	0.151 (5)	0.056 (2)	−0.001 (3)	0.005 (2)	−0.009 (3)
C9	0.065 (2)	0.059 (2)	0.0437 (18)	0.0001 (17)	0.0039 (17)	−0.0034 (16)
C10	0.067 (2)	0.078 (3)	0.0436 (17)	0.0013 (19)	0.0028 (17)	−0.0034 (18)
C11	0.071 (3)	0.114 (4)	0.053 (2)	0.005 (3)	0.014 (2)	−0.011 (2)
C12	0.087 (3)	0.115 (4)	0.0447 (19)	−0.001 (3)	0.009 (2)	−0.015 (2)
C13	0.082 (3)	0.089 (3)	0.052 (2)	−0.006 (2)	−0.002 (2)	−0.010 (2)
C14	0.071 (3)	0.072 (3)	0.0518 (19)	−0.002 (2)	−0.0041 (19)	−0.0090 (18)
C15	0.076 (3)	0.137 (5)	0.065 (2)	0.007 (3)	−0.006 (2)	−0.023 (3)
C16	0.082 (4)	0.205 (8)	0.095 (4)	0.002 (4)	−0.020 (3)	−0.043 (4)
C17	0.097 (4)	0.196 (8)	0.081 (3)	0.002 (4)	−0.030 (3)	−0.027 (4)
C18	0.103 (4)	0.153 (5)	0.054 (2)	−0.013 (4)	−0.012 (3)	−0.025 (3)

Geometric parameters (Å, º) top

O1—C1	1.353 (5)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.3900
N1—C8	1.291 (6)	C5—H5	0.9300
N1—C10	1.411 (5)	C6—C8	1.451 (6)
O2'—C7'	1.369 (13)	C7—H7A	0.9600
O2'—C2'	1.378 (11)	C7—H7B	0.9600
C1'—C2'	1.3900	C7—H7C	0.9600
C1'—C6'	1.3900	C8—H8	0.9300
C2'—C3'	1.3900	C9—C10	1.372 (6)
C3'—C4'	1.3900	C9—C14	1.420 (5)
C3'—H3'	0.9300	C9—C9ⁱ	1.512 (7)
C4'—C5'	1.3900	C10—C11	1.419 (5)
C4'—H4'	0.9300	C11—C12	1.340 (6)
C5'—C6'	1.3900	C11—H11	0.9300
C5'—H5'	0.9300	C12—C13	1.419 (7)
C7'—H7A'	0.9600	C12—H12	0.9300
C7'—H7B'	0.9600	C13—C18	1.385 (6)
C7'—H7C'	0.9600	C13—C14	1.416 (6)
O2—C7	1.365 (9)	C14—C15	1.419 (7)
O2—C2	1.386 (6)	C15—C16	1.355 (7)
C1—C2	1.3900	C15—H15	0.9300
C1—C6	1.3900	C16—C17	1.403 (8)
C2—C3	1.3900	C16—H16	0.9300
C3—C4	1.3900	C17—C18	1.350 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.3900	C18—H18	0.9300

C8—N1—C10	121.1 (4)	C1—C6—C8	121.5 (5)
C7'—O2'—C2'	117.7 (14)	O2—C7—H7A	109.5
C2'—C1'—C6'	120.0	O2—C7—H7B	109.5
O2'—C2'—C1'	121.3 (17)	H7A—C7—H7B	109.5
O2'—C2'—C3'	118.7 (17)	O2—C7—H7C	109.5
C1'—C2'—C3'	120.0	H7A—C7—H7C	109.5
C4'—C3'—C2'	120.0	H7B—C7—H7C	109.5
C4'—C3'—H3'	120.0	N1—C8—C6	120.3 (4)
C2'—C3'—H3'	120.0	N1—C8—H8	119.8
C3'—C4'—C5'	120.0	C6—C8—H8	119.8
C3'—C4'—H4'	120.0	C10—C9—C14	119.4 (3)
C5'—C4'—H4'	120.0	C10—C9—C9ⁱ	120.2 (3)
C6'—C5'—C4'	120.0	C14—C9—C9ⁱ	120.5 (4)
C6'—C5'—H5'	120.0	C9—C10—N1	117.8 (3)
C4'—C5'—H5'	120.0	C9—C10—C11	119.9 (4)
C5'—C6'—C1'	120.0	N1—C10—C11	122.3 (4)
O2'—C7'—H7A'	109.5	C12—C11—C10	121.4 (4)
O2'—C7'—H7B'	109.5	C12—C11—H11	119.3
H7A'—C7'—H7B'	109.5	C10—C11—H11	119.3
O2'—C7'—H7C'	109.5	C11—C12—C13	121.0 (4)
H7A'—C7'—H7C'	109.5	C11—C12—H12	119.5
H7B'—C7'—H7C'	109.5	C13—C12—H12	119.5
C7—O2—C2	118.4 (8)	C18—C13—C14	120.2 (5)
O1—C1—C2	117.9 (5)	C18—C13—C12	121.8 (4)
O1—C1—C6	122.1 (5)	C14—C13—C12	118.0 (4)
C2—C1—C6	120.0	C13—C14—C15	117.4 (4)
O2—C2—C3	126.5 (6)	C13—C14—C9	120.4 (4)
O2—C2—C1	113.5 (6)	C15—C14—C9	122.3 (4)
C3—C2—C1	120.0	C16—C15—C14	120.9 (5)
C4—C3—C2	120.0	C16—C15—H15	119.5
C4—C3—H3	120.0	C14—C15—H15	119.5
C2—C3—H3	120.0	C15—C16—C17	120.3 (6)
C3—C4—C5	120.0	C15—C16—H16	119.8
C3—C4—H4	120.0	C17—C16—H16	119.8
C5—C4—H4	120.0	C18—C17—C16	120.2 (5)
C6—C5—C4	120.0	C18—C17—H17	119.9
C6—C5—H5	120.0	C16—C17—H17	119.9
C4—C5—H5	120.0	C17—C18—C13	120.9 (5)
C5—C6—C1	120.0	C17—C18—H18	119.5
C5—C6—C8	118.5 (5)	C13—C18—H18	119.5

C7'—O2'—C2'—C1'	178.9 (8)	C1—C6—C8—N1	7.5 (7)
C7'—O2'—C2'—C3'	−1.8 (14)	C14—C9—C10—N1	−178.7 (4)
C6'—C1'—C2'—O2'	179.3 (7)	C9ⁱ—C9—C10—N1	2.0 (6)
C6'—C1'—C2'—C3'	0.0	C14—C9—C10—C11	−0.1 (6)
O2'—C2'—C3'—C4'	−179.3 (6)	C9ⁱ—C9—C10—C11	−179.3 (4)
C1'—C2'—C3'—C4'	0.0	C8—N1—C10—C9	−154.8 (4)
C2'—C3'—C4'—C5'	0.0	C8—N1—C10—C11	26.6 (7)
C3'—C4'—C5'—C6'	0.0	C9—C10—C11—C12	0.8 (7)
C4'—C5'—C6'—C1'	0.0	N1—C10—C11—C12	179.4 (5)
C2'—C1'—C6'—C5'	0.0	C10—C11—C12—C13	0.1 (8)
C7—O2—C2—C3	1.4 (11)	C11—C12—C13—C18	−180.0 (5)
C7—O2—C2—C1	−178.3 (7)	C11—C12—C13—C14	−1.5 (8)
O1—C1—C2—O2	1.3 (6)	C18—C13—C14—C15	−0.4 (7)
C6—C1—C2—O2	179.7 (5)	C12—C13—C14—C15	−178.9 (5)
O1—C1—C2—C3	−178.4 (4)	C18—C13—C14—C9	−179.4 (5)
C6—C1—C2—C3	0.0	C12—C13—C14—C9	2.1 (7)
O2—C2—C3—C4	−179.7 (5)	C10—C9—C14—C13	−1.4 (6)
C1—C2—C3—C4	0.0	C9ⁱ—C9—C14—C13	177.9 (4)
C2—C3—C4—C5	0.0	C10—C9—C14—C15	179.8 (5)
C3—C4—C5—C6	0.0	C9ⁱ—C9—C14—C15	−1.0 (6)
C4—C5—C6—C1	0.0	C13—C14—C15—C16	0.1 (9)
C4—C5—C6—C8	−177.8 (4)	C9—C14—C15—C16	179.0 (6)
O1—C1—C6—C5	178.4 (5)	C14—C15—C16—C17	0.2 (11)
C2—C1—C6—C5	0.0	C15—C16—C17—C18	−0.3 (13)
O1—C1—C6—C8	−3.9 (5)	C16—C17—C18—C13	0.0 (12)
C2—C1—C6—C8	177.7 (4)	C14—C13—C18—C17	0.4 (10)
C10—N1—C8—C6	179.6 (4)	C12—C13—C18—C17	178.8 (6)
C5—C6—C8—N1	−174.8 (4)

Symmetry code: (i) y, x, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.575 (4)	145

Experimental details

Crystal data
Chemical formula	C₃₆H₂₈N₂O₄
M_r	552.60
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	295
a, c (Å)	11.3285 (6), 23.837 (1)
V (Å³)	3059.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.38 × 0.31 × 0.28

Data collection
Diffractometer	Bruker APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15298, 1629, 1190
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.203, 1.10
No. of reflections	1629
No. of parameters	240
No. of restraints	114
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.575 (4)	145

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(S)-(+)-2,2'-Bis(2-hydr­oxy-3-methoxy­benzyl­ideneamino)-1,1'-binaphth­yl