1,6-Bis(2-furyl)-2,5-bis(3-formyl-2-hydroxy-5-methyl­benzyl)-2,5-di­aza­hexane

The title compound, C₃₀H₃₂N₂O₆, has a center of symmetry. There are two intramol­ecular O—H...N hydrogen bonds, with an O...N distance of 2.686 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.135
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART and SAINT (Bruker, 1997); data reduction: XPREP (Bruker, 1997); 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: SHELXTL (Bruker, 1997).

1,6-bis(2-furyl)-2,5-bis(3-formyl-2-hydroxy-5-methylbenzyl)-2,5-diazahexane

Crystal data

C30H32N2O6	F(000) = 548
Mr = 516.58	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Melting point = 382–383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.306 (1) Å	Cell parameters from 1184 reflections
b = 16.625 (4) Å	θ = 1.1–25.0°
c = 15.020 (1) Å	µ = 0.09 mm^−1
β = 92.06 (1)°	T = 293 K
V = 1324.1 (4) Å^3	Prismatic, colorless
Z = 2	0.30 × 0.20 × 0.20 mm

Data collection

Bruker CCD area-detector diffractometer	2336 independent reflections
Radiation source: fine-focus sealed tube	1988 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1997)	h = −6→6
Tmin = 0.979, Tmax = 0.982	k = 0→19
3224 measured reflections	l = 0→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.25P] where P = (Fo^2 + 2Fc^2)/3
2336 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

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	0.2170 (5)	−0.03354 (18)	0.69372 (17)	0.0449 (6)
H1	0.0918	−0.0161	0.6533	0.054*
C2	0.2475 (6)	−0.10949 (18)	0.72378 (17)	0.0460 (6)
H2	0.1519	−0.1539	0.7059	0.055*
C3	0.4536 (4)	−0.10947 (13)	0.78819 (15)	0.0291 (4)
H3	0.5146	−0.1531	0.8212	0.035*
C4	0.5388 (4)	−0.03548 (12)	0.79103 (15)	0.0281 (4)
C5	0.7435 (3)	0.00422 (11)	0.84683 (14)	0.0210 (4)
H5A	0.8401	−0.0372	0.8781	0.025*
H5B	0.8564	0.0316	0.8075	0.025*
C6	0.4523 (3)	0.03328 (11)	0.96933 (13)	0.0196 (4)
H6A	0.3128	0.0134	0.9320	0.024*
H6B	0.3910	0.0776	1.0046	0.024*
C7	0.5972 (5)	0.14228 (12)	0.87441 (15)	0.0300 (5)
H7A	0.4316	0.1402	0.8449	0.036*
H7B	0.7183	0.1544	0.8295	0.036*
C8	0.6000 (3)	0.20934 (11)	0.94109 (13)	0.0174 (4)
C9	0.7854 (3)	0.21087 (12)	1.01042 (14)	0.0213 (4)
C10	0.8008 (4)	0.27395 (12)	1.07168 (14)	0.0227 (4)
C11	0.6258 (4)	0.33906 (12)	1.05956 (16)	0.0264 (4)
H11	0.6332	0.3823	1.0988	0.032*
C12	0.4401 (4)	0.33873 (12)	0.98823 (16)	0.0270 (4)
C13	0.4269 (4)	0.27259 (12)	0.93247 (15)	0.0264 (4)
H13	0.3001	0.2701	0.8882	0.032*
C14	0.2610 (4)	0.41087 (12)	0.97582 (16)	0.0256 (4)
H14A	0.1520	0.4023	0.9243	0.038*
H14B	0.3578	0.4590	0.9679	0.038*
H14C	0.1612	0.4164	1.0275	0.038*
C15	0.9784 (5)	0.27817 (16)	1.14298 (18)	0.0408 (6)
H15	1.0913	0.2354	1.1469	0.049*
N1	0.6563 (3)	0.06221 (9)	0.91234 (11)	0.0191 (4)
O1	0.4062 (3)	0.01476 (10)	0.73373 (10)	0.0364 (4)
O2	0.9566 (3)	0.15113 (9)	1.02132 (11)	0.0296 (4)
H2A	0.9321	0.1170	0.9825	0.044*
O3	1.0076 (3)	0.32955 (12)	1.20085 (14)	0.0495 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0406 (14)	0.0575 (13)	0.0261 (12)	−0.0056 (11)	−0.0072 (9)	−0.0055 (10)
C2	0.0483 (15)	0.0499 (11)	0.0297 (12)	−0.0138 (11)	−0.0005 (10)	−0.0115 (10)
C3	0.0405 (11)	0.0193 (8)	0.0280 (11)	0.0040 (7)	0.0082 (8)	−0.0089 (7)
C4	0.0386 (11)	0.0170 (8)	0.0286 (10)	0.0074 (7)	0.0013 (7)	−0.0030 (7)
C5	0.0122 (8)	0.0211 (9)	0.0304 (10)	0.0070 (6)	0.0078 (6)	0.0011 (7)
C6	0.0108 (8)	0.0180 (9)	0.0306 (11)	0.0057 (7)	0.0066 (7)	−0.0004 (7)
C7	0.0480 (13)	0.0175 (8)	0.0247 (10)	0.0051 (8)	0.0028 (8)	0.0033 (6)
C8	0.0143 (8)	0.0153 (7)	0.0228 (9)	−0.0036 (6)	0.0040 (6)	0.0064 (6)
C9	0.0111 (8)	0.0218 (9)	0.0313 (10)	0.0026 (6)	0.0057 (6)	0.0023 (6)
C10	0.0220 (9)	0.0212 (9)	0.0253 (9)	0.0007 (6)	0.0067 (7)	0.0013 (6)
C11	0.0170 (9)	0.0169 (9)	0.0458 (12)	−0.0054 (6)	0.0089 (7)	0.0064 (7)
C12	0.0206 (9)	0.0190 (8)	0.0422 (11)	0.0045 (7)	0.0156 (7)	0.0109 (7)
C13	0.0244 (10)	0.0171 (8)	0.0379 (11)	0.0035 (7)	0.0056 (8)	0.0144 (6)
C14	0.0150 (9)	0.0240 (9)	0.0386 (12)	0.0051 (7)	0.0101 (7)	−0.0005 (8)
C15	0.0255 (11)	0.0447 (14)	0.0519 (14)	−0.0028 (9)	−0.0029 (9)	−0.0079 (9)
N1	0.0108 (7)	0.0177 (7)	0.0293 (9)	0.0059 (6)	0.0052 (6)	0.0003 (6)
O1	0.0487 (10)	0.0356 (8)	0.0240 (8)	−0.0082 (7)	−0.0086 (7)	0.0058 (6)
O2	0.0167 (7)	0.0296 (8)	0.0416 (9)	0.0048 (5)	−0.0100 (6)	−0.0162 (7)
O3	0.0312 (10)	0.0563 (12)	0.0599 (12)	0.0011 (8)	−0.0133 (8)	−0.0174 (9)

Geometric parameters (Å, º)

C1—C2	1.349 (4)	C7—H7B	0.9700
C1—O1	1.404 (3)	C8—C13	1.399 (3)
C1—H1	0.9300	C8—C9	1.407 (3)
C2—C3	1.434 (4)	C9—O2	1.352 (2)
C2—H2	0.9300	C9—C10	1.396 (3)
C3—C4	1.310 (3)	C10—C15	1.403 (3)
C3—H3	0.9300	C10—C11	1.434 (3)
C4—O1	1.375 (3)	C11—C12	1.429 (3)
C4—C5	1.501 (3)	C11—H11	0.9300
C5—N1	1.464 (2)	C12—C13	1.382 (3)
C5—H5A	0.9700	C12—C14	1.537 (3)
C5—H5B	0.9700	C13—H13	0.9300
C6—N1	1.484 (2)	C14—H14A	0.9600
C6—C6^i	1.515 (4)	C14—H14B	0.9600
C6—H6A	0.9700	C14—H14C	0.9600
C6—H6B	0.9700	C15—O3	1.224 (3)
C7—N1	1.477 (2)	C15—H15	0.9300
C7—C8	1.498 (3)	O2—H2A	0.8200
C7—H7A	0.9700
C2—C1—O1	108.5 (2)	C13—C8—C7	120.44 (19)
C2—C1—H1	125.8	C9—C8—C7	119.89 (18)
O1—C1—H1	125.8	O2—C9—C10	116.67 (19)
C1—C2—C3	107.7 (2)	O2—C9—C8	121.68 (18)
C1—C2—H2	126.1	C10—C9—C8	121.64 (18)
C3—C2—H2	126.1	C9—C10—C15	124.3 (2)
C4—C3—C2	106.0 (2)	C9—C10—C11	117.5 (2)
C4—C3—H3	127.0	C15—C10—C11	118.3 (2)
C2—C3—H3	127.0	C12—C11—C10	121.2 (2)
C3—C4—O1	112.5 (2)	C12—C11—H11	119.4
C3—C4—C5	132.3 (2)	C10—C11—H11	119.4
O1—C4—C5	115.23 (17)	C13—C12—C11	118.40 (19)
N1—C5—C4	115.14 (15)	C13—C12—C14	122.0 (2)
N1—C5—H5A	108.5	C11—C12—C14	119.63 (19)
C4—C5—H5A	108.5	C12—C13—C8	121.5 (2)
N1—C5—H5B	108.5	C12—C13—H13	119.2
C4—C5—H5B	108.5	C8—C13—H13	119.2
H5A—C5—H5B	107.5	C12—C14—H14A	109.5
N1—C6—C6^i	110.63 (17)	C12—C14—H14B	109.5
N1—C6—H6A	109.5	H14A—C14—H14B	109.5
C6^i—C6—H6A	109.5	C12—C14—H14C	109.5
N1—C6—H6B	109.5	H14A—C14—H14C	109.5
C6^i—C6—H6B	109.5	H14B—C14—H14C	109.5
H6A—C6—H6B	108.1	O3—C15—C10	129.9 (2)
N1—C7—C8	114.57 (17)	O3—C15—H15	115.1
N1—C7—H7A	108.6	C10—C15—H15	115.1
C8—C7—H7A	108.6	C5—N1—C7	113.70 (16)
N1—C7—H7B	108.6	C5—N1—C6	115.40 (15)
C8—C7—H7B	108.6	C7—N1—C6	111.43 (15)
H7A—C7—H7B	107.6	C4—O1—C1	105.21 (19)
C13—C8—C9	119.60 (19)	C9—O2—H2A	109.5

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	1.99	2.686 (2)	142