N,N'-1,2-Ethanediylbis{2-[(N-benzyl­carbamo­yl)meth­oxy]benzamide}

The title compound, C₃₄H₃₄N₄O₆, has been synthesized by the reaction of N,N'-1,2-ethanediylbis(2-hydroxy­benzamide) with N-benzyl-2-chloro­acetamide and crystallized from DMF. Individual mol­ecules possess crystallographically imposed inversion symmetry. There are intra­molecular hydrogen bonds between the phen­oxy O atoms and the benzamide N atoms. Inter­molecular hydrogen bonds between amide N and amide O atoms of neighbouring mol­ecules allow the construction of a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C34 H34 N4 O6

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

N,N'-1,2-Ethanediylbis{2-[(N-benzylcarbamoyl)methoxy]benzamide}

Crystal data

C34H34N4O6	F(000) = 628
Mr = 594.65	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Melting point = 484–486 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7401 (3) Å	Cell parameters from 2350 reflections
b = 13.6100 (4) Å	θ = 2.2–26.8°
c = 8.8838 (2) Å	µ = 0.09 mm^−1
β = 105.457 (1)°	T = 294 K
V = 1484.67 (7) Å^3	Block, colourless
Z = 2	0.42 × 0.28 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	2210 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.022
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
π and ω scans	h = −15→15
8214 measured reflections	k = −13→16
2913 independent reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.258P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2913 reflections	Δρmax = 0.26 e Å^−3
200 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (18)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.17595 (11)	0.25771 (11)	0.91492 (16)	0.0504 (4)
H1'	0.1870	0.2874	0.8350	0.060*
N2	0.49183 (10)	0.03475 (10)	1.29381 (14)	0.0426 (3)
H2'	0.4476	0.0788	1.2439	0.051*
O1	0.25705 (9)	0.17763 (9)	1.13967 (12)	0.0518 (3)
O2	0.44671 (8)	0.17085 (9)	1.07389 (12)	0.0481 (3)
O3	0.64868 (10)	−0.04712 (9)	1.32030 (14)	0.0573 (4)
C1	−0.00411 (13)	0.17964 (13)	0.8242 (2)	0.0516 (4)
C2	0.02140 (18)	0.08153 (17)	0.8445 (3)	0.0854 (7)
H2	0.0806	0.0622	0.9253	0.103*
C3	−0.0388 (2)	0.0116 (2)	0.7479 (4)	0.1148 (11)
H3	−0.0208	−0.0545	0.7649	0.138*
C4	−0.1257 (2)	0.0384 (2)	0.6259 (3)	0.0975 (8)
H4	−0.1644	−0.0088	0.5575	0.117*
C5	−0.15405 (16)	0.1345 (2)	0.6067 (3)	0.0795 (7)
H5	−0.2140	0.1532	0.5265	0.095*
C6	−0.09416 (14)	0.20525 (16)	0.7060 (2)	0.0653 (6)
H6	−0.1151	0.2708	0.6926	0.078*
C7	0.06510 (13)	0.25416 (14)	0.9312 (2)	0.0558 (5)
H7A	0.0320	0.3185	0.9084	0.067*
H7B	0.0674	0.2381	1.0384	0.067*
C8	0.26126 (12)	0.21738 (11)	1.01725 (17)	0.0399 (4)
C9	0.36552 (12)	0.22538 (12)	0.96690 (18)	0.0435 (4)
H9A	0.3546	0.1993	0.8622	0.052*
H9B	0.3874	0.2936	0.9668	0.052*
C10	0.54140 (11)	0.14867 (11)	1.03464 (17)	0.0383 (4)
C11	0.57218 (13)	0.19701 (12)	0.91583 (18)	0.0464 (4)
H11	0.5281	0.2462	0.8594	0.056*
C12	0.66791 (14)	0.17220 (13)	0.8813 (2)	0.0532 (4)
H12	0.6879	0.2046	0.8010	0.064*
C13	0.73428 (14)	0.09991 (14)	0.9643 (2)	0.0572 (5)
H13	0.7987	0.0831	0.9403	0.069*
C14	0.70393 (13)	0.05271 (13)	1.0837 (2)	0.0488 (4)
H14	0.7494	0.0045	1.1405	0.059*
C15	0.60748 (12)	0.07487 (11)	1.12169 (16)	0.0377 (4)
C16	0.58391 (12)	0.01605 (11)	1.25268 (17)	0.0404 (4)
C17	0.46568 (13)	−0.01805 (12)	1.42096 (17)	0.0451 (4)
H17A	0.4785	−0.0877	1.4107	0.054*
H17B	0.3891	−0.0091	1.4150	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0410 (7)	0.0637 (9)	0.0484 (8)	0.0040 (6)	0.0151 (6)	0.0121 (7)
N2	0.0453 (7)	0.0494 (8)	0.0333 (7)	0.0038 (6)	0.0111 (6)	0.0074 (6)
O1	0.0594 (7)	0.0622 (8)	0.0377 (6)	0.0013 (6)	0.0199 (5)	0.0056 (5)
O2	0.0456 (6)	0.0638 (7)	0.0375 (6)	0.0158 (5)	0.0153 (5)	0.0130 (5)
O3	0.0580 (7)	0.0619 (8)	0.0519 (7)	0.0166 (6)	0.0144 (6)	0.0145 (6)
C1	0.0388 (9)	0.0639 (11)	0.0562 (10)	0.0073 (8)	0.0197 (8)	0.0088 (9)
C2	0.0630 (13)	0.0722 (14)	0.1054 (18)	0.0204 (11)	−0.0047 (12)	−0.0056 (13)
C3	0.0888 (19)	0.0798 (17)	0.153 (3)	0.0148 (14)	−0.0065 (19)	−0.0320 (18)
C4	0.0686 (15)	0.111 (2)	0.107 (2)	−0.0046 (14)	0.0117 (14)	−0.0314 (17)
C5	0.0456 (11)	0.119 (2)	0.0682 (14)	−0.0072 (12)	0.0045 (10)	0.0161 (13)
C6	0.0441 (10)	0.0782 (13)	0.0743 (13)	0.0043 (9)	0.0169 (9)	0.0244 (11)
C7	0.0475 (10)	0.0641 (11)	0.0608 (11)	0.0096 (8)	0.0232 (8)	0.0054 (9)
C8	0.0463 (9)	0.0394 (8)	0.0350 (8)	−0.0013 (7)	0.0125 (7)	−0.0036 (7)
C9	0.0421 (8)	0.0474 (9)	0.0402 (8)	0.0032 (7)	0.0094 (7)	0.0076 (7)
C10	0.0382 (8)	0.0443 (8)	0.0329 (8)	−0.0025 (6)	0.0107 (6)	−0.0044 (6)
C11	0.0498 (9)	0.0482 (9)	0.0415 (9)	−0.0018 (7)	0.0129 (7)	0.0051 (7)
C12	0.0534 (10)	0.0633 (11)	0.0476 (10)	−0.0090 (8)	0.0218 (8)	0.0033 (8)
C13	0.0449 (9)	0.0710 (12)	0.0609 (11)	0.0004 (8)	0.0231 (8)	0.0012 (9)
C14	0.0420 (9)	0.0561 (10)	0.0492 (10)	0.0040 (7)	0.0138 (7)	0.0027 (8)
C15	0.0383 (8)	0.0416 (8)	0.0319 (8)	−0.0021 (6)	0.0070 (6)	−0.0041 (6)
C16	0.0438 (8)	0.0432 (9)	0.0326 (8)	−0.0002 (7)	0.0073 (6)	−0.0012 (7)
C17	0.0505 (9)	0.0505 (9)	0.0345 (8)	−0.0046 (7)	0.0114 (7)	0.0058 (7)

Geometric parameters (Å, º)

C1—C2	1.375 (3)	C10—O2	1.3757 (18)
C1—C6	1.377 (2)	C10—C11	1.386 (2)
C1—C7	1.505 (2)	C10—C15	1.403 (2)
C2—C3	1.371 (3)	C11—C12	1.377 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.376 (4)	C12—C13	1.376 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.356 (4)	C13—C14	1.380 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.389 (3)	C14—C15	1.391 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.507 (2)
C7—N1	1.458 (2)	C16—O3	1.2315 (18)
C7—H7A	0.9700	C16—N2	1.343 (2)
C7—H7B	0.9700	C17—N2	1.4506 (19)
C8—O1	1.2286 (18)	C17—C17^i	1.524 (3)
C8—N1	1.3351 (19)	C17—H17A	0.9700
C8—C9	1.514 (2)	C17—H17B	0.9700
C9—O2	1.4142 (17)	N1—H1'	0.8600
C9—H9A	0.9700	N2—H2'	0.8600
C9—H9B	0.9700
C2—C1—C6	117.75 (19)	O2—C10—C15	117.08 (13)
C2—C1—C7	119.57 (16)	C11—C10—C15	120.63 (14)
C6—C1—C7	122.68 (17)	C12—C11—C10	120.04 (16)
C3—C2—C1	121.3 (2)	C12—C11—H11	120.0
C3—C2—H2	119.4	C10—C11—H11	120.0
C1—C2—H2	119.4	C11—C12—C13	120.67 (16)
C2—C3—C4	120.5 (3)	C11—C12—H12	119.7
C2—C3—H3	119.8	C13—C12—H12	119.7
C4—C3—H3	119.8	C12—C13—C14	119.10 (16)
C5—C4—C3	119.1 (2)	C12—C13—H13	120.4
C5—C4—H4	120.4	C14—C13—H13	120.4
C3—C4—H4	120.4	C13—C14—C15	122.14 (16)
C4—C5—C6	120.4 (2)	C13—C14—H14	118.9
C4—C5—H5	119.8	C15—C14—H14	118.9
C6—C5—H5	119.8	C14—C15—C10	117.40 (14)
C1—C6—C5	120.9 (2)	C14—C15—C16	116.29 (14)
C1—C6—H6	119.5	C10—C15—C16	126.31 (13)
C5—C6—H6	119.5	O3—C16—N2	121.34 (14)
N1—C7—C1	112.29 (14)	O3—C16—C15	120.13 (14)
N1—C7—H7A	109.1	N2—C16—C15	118.53 (13)
C1—C7—H7A	109.1	N2—C17—C17^i	111.30 (16)
N1—C7—H7B	109.1	N2—C17—H17A	109.4
C1—C7—H7B	109.1	C17^i—C17—H17A	109.4
H7A—C7—H7B	107.9	N2—C17—H17B	109.4
O1—C8—N1	124.34 (15)	C17^i—C17—H17B	109.4
O1—C8—C9	122.81 (14)	H17A—C17—H17B	108.0
N1—C8—C9	112.85 (13)	C8—N1—C7	123.57 (14)
O2—C9—C8	107.81 (12)	C8—N1—H1'	118.2
O2—C9—H9A	110.1	C7—N1—H1'	118.2
C8—C9—H9A	110.1	C16—N2—C17	121.10 (13)
O2—C9—H9B	110.1	C16—N2—H2'	119.4
C8—C9—H9B	110.1	C17—N2—H2'	119.4
H9A—C9—H9B	108.5	C10—O2—C9	118.59 (12)
O2—C10—C11	122.28 (14)
C6—C1—C2—C3	1.8 (4)	C13—C14—C15—C16	178.86 (15)
C7—C1—C2—C3	−179.0 (2)	O2—C10—C15—C14	−179.38 (13)
C1—C2—C3—C4	1.1 (5)	C11—C10—C15—C14	−0.1 (2)
C2—C3—C4—C5	−3.0 (5)	O2—C10—C15—C16	1.1 (2)
C3—C4—C5—C6	1.9 (4)	C11—C10—C15—C16	−179.54 (14)
C2—C1—C6—C5	−2.8 (3)	C14—C15—C16—O3	0.4 (2)
C7—C1—C6—C5	178.06 (17)	C10—C15—C16—O3	179.93 (14)
C4—C5—C6—C1	1.0 (3)	C14—C15—C16—N2	179.96 (13)
C2—C1—C7—N1	64.8 (2)	C10—C15—C16—N2	−0.6 (2)
C6—C1—C7—N1	−116.13 (18)	O1—C8—N1—C7	−4.0 (2)
O1—C8—C9—O2	6.5 (2)	C9—C8—N1—C7	175.95 (15)
N1—C8—C9—O2	−173.38 (13)	C1—C7—N1—C8	−103.28 (19)
O2—C10—C11—C12	179.87 (14)	O3—C16—N2—C17	0.7 (2)
C15—C10—C11—C12	0.6 (2)	C15—C16—N2—C17	−178.78 (12)
C10—C11—C12—C13	−0.4 (3)	C17^i—C17—N2—C16	75.2 (2)
C11—C12—C13—C14	−0.3 (3)	C11—C10—O2—C9	16.5 (2)
C12—C13—C14—C15	0.9 (3)	C15—C10—O2—C9	−164.18 (13)
C13—C14—C15—C10	−0.7 (2)	C8—C9—O2—C10	165.77 (12)

Symmetry code: (i) −x+1, −y, −z+3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O2	0.86	1.96	2.642 (3)	135
N1—H1′···O1^ii	0.86	2.20	3.028 (3)	160

Symmetry code: (ii) x, −y+1/2, z−1/2.