6,6′-Dimeth­oxy-2,2′-(o-phenyl­ene­diimino)­diphenol

Liu, Y.-F.; Xia, H.-T.; Yang, S.-P.; Wang, D.-Q.

doi:10.1107/S1600536807027778

6,6′-Dimethoxy-2,2′-(o-phenylenediimino)diphenol

Y.-F. Liu, H.-T. Xia, S.-P. Yang and D.-Q. Wang

In the title compound, C₂₂H₂₄N₂O₄, the dihedral angles between the central benzene ring and the other two benzene rings are 70.26 (8) and 84.40 (8)°. The molecules are linked into chains running parallel to the [001] direction by O—H

N and N—H

O hydrogen bonds, and adjacent chains are linked into sheets parallel to the (001) plane by C—H

π hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027778/at2321sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027778/at2321Isup2.hkl Contains datablock I

CCDC reference: 649513

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.096
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       6.11 su
PLAT416_ALERT_2_C Short Intra D-H..H-D       H1     ..  H2      ..       1.93 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for N1     ..  N2      ..      99.60 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C7     ..  O1      ..      90.00 Deg.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 237
              \%A (aryl), 0.96 \%A (methyl), 0.97 \%A (methylene), U~iso~(H) = 1.2 (C~aryl ,
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~
PUBL022_ALERT_1_A There is a mismatched ~ on line 238
              methylene~) or 1.5 U~eq~(C~methyl~).
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Comment top

As part of our investigation of o-vanillin diamine derivatives, we have recently reported the crystal structure of N,N'-(2-hydroxy-3-methoxy benzyl benzene-1,4-diamine (II) (Xia et al., 2007) and N,N'-(2-hydroxy-3-methoxy benzyl) benzene-1,3-diamine (III) (Liu et al., 2007), we report here the their isocompound, crystal structure of N,N'-(2-hydroxy-3-methoxy benzyl benzene-1,2-diamine, (I).

In the molecule, the dihedral angle between the certral benzen ring and another two benzen rings are 70.26(0.08)°(C9—C13 benzen ring) and 84.40(0.08)°(C16—C21 benzen ring), respectively (Fig. 1). Its bond lengths and angles are similar with compounds (II), (III) and are normal (Allen et al., 1987). The principal difference between compounds (I) and (II), (III) concerns the intermoleculae aggregation. In (I), The molecular are linked into chains running parallel to the [001] directions by O—H···N and N—H···O hydrogen bonds. Atoms O1 and O3 in the molecule (x, y, z) act as hydrogen-bond donors to atoms N1 in the molecule (-1/2 + x, y, 3/2 - z) and N2 in the molecule (1/2 + x, y, 3/2 - z), respectively, in addition, atom N2 in the molecule (x, y, z) act as hydrogen-bond donor to atom O4 in the molecule (-1/2 + x, y, 3/2 - z), forming a chain of R₂²(7) ring (Bernstein et al., 1995) running parallel to the [001] direction (Fig. 2 and Table 1), adjacent chains are linked into sheets parallel to the [001] plane by C—H···π hydrogen bonds (Fig. 3). There are no direction-specific interactions between adjacent sheets and are in agreement with their isocompound. By contrast, in (II), the molecule are linked into sheets by means of N—H···O and O—H···N hydrogen-bonds and in (III), the molecule are linked into sheets by means of O—H···O and C—H···π hydrogen-bonds, they are absent from the structure of (I).

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).

Experimental top

Solutions of N,N'-bis(2-hydroxy-3-methoxy benzylene)benzene-1,2-diamine (20 mmol) in methanol–chloroform (v/v = 1/1) (40 ml) and NaBH₄ (80 mmol) were mixed, the mixture solution was stirred under room temperature for 48 h and then mixtures was filtered, and then solution was left to produce crystals of (I) slowly.

Structure description top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level.
	Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chains built from O—H···N and N—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry code: (A) -1/2 + x, y, 3/2 - z; (B) 1/2 + x, y, 3/2 - z].
	Fig. 3. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded sheets built from C—H···π. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry code: (A) -1/2 + x, y, 3/2 - z; (B) 1/2 + x, y, 3/2 - z; (C) 3/2 - x, -1/2 + y, z; (D) 2 - x, -1/2 + y, 3/2 - z; (E) 1 - x, -1/2 + y, 3/2 - z].

6,6'-Dimethoxy-2,2'-(o-phenylenediimino)diphenol top

Crystal data top

C₂₂H₂₄N₂O₄	F(000) = 1616
M_r = 380.43	D_x = 1.313 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1282 reflections
a = 10.4331 (14) Å	θ = 2.6–18.5°
b = 15.7674 (16) Å	µ = 0.09 mm⁻¹
c = 23.398 (2) Å	T = 298 K
V = 3849.1 (7) Å³	Acerate, red
Z = 8	0.38 × 0.21 × 0.10 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.966, T_max = 0.991	k = −18→9
14963 measured reflections	l = −27→27

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ²(F_o²) + (0.0315P)²] where P = (F_o² + 2F_c²)/3
3383 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₂₄N₂O₄	V = 3849.1 (7) Å³
M_r = 380.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.4331 (14) Å	µ = 0.09 mm⁻¹
b = 15.7674 (16) Å	T = 298 K
c = 23.398 (2) Å	0.38 × 0.21 × 0.10 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3383 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1530 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.991	R_int = 0.091
14963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.12 e Å⁻³
3383 reflections	Δρ_min = −0.17 e Å⁻³
265 parameters

Special details top

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
N1	0.5932 (2)	0.84158 (13)	0.71070 (9)	0.0485 (6)
H1	0.566 (2)	0.8767 (14)	0.7378 (9)	0.058*
N2	0.5906 (2)	1.00932 (13)	0.68887 (9)	0.0456 (6)
H2	0.644 (2)	0.9819 (14)	0.7137 (9)	0.055*
O1	0.36186 (18)	0.82490 (13)	0.78154 (8)	0.0624 (6)
H1A	0.288 (3)	0.8358 (19)	0.7969 (12)	0.094*
O2	0.32169 (19)	0.83823 (12)	0.89338 (7)	0.0701 (6)
O3	0.86629 (16)	1.03619 (11)	0.73032 (7)	0.0534 (5)
H3	0.938 (3)	1.0251 (17)	0.7482 (11)	0.080*
O4	1.08934 (18)	0.99872 (13)	0.68090 (8)	0.0696 (6)
C1	0.5414 (2)	0.86734 (17)	0.65774 (10)	0.0450 (7)
C2	0.5445 (2)	0.95466 (16)	0.64562 (10)	0.0416 (6)
C3	0.4963 (2)	0.98313 (18)	0.59464 (10)	0.0536 (7)
H3A	0.4980	1.0408	0.5864	0.064*
C4	0.4451 (3)	0.9273 (2)	0.55528 (12)	0.0678 (9)
H4	0.4110	0.9476	0.5212	0.081*
C5	0.4446 (3)	0.8420 (2)	0.56652 (12)	0.0756 (10)
H5	0.4114	0.8043	0.5398	0.091*
C6	0.4933 (3)	0.81202 (18)	0.61745 (12)	0.0617 (8)
H6	0.4937	0.7540	0.6247	0.074*
C7	0.5696 (3)	0.75466 (15)	0.73205 (11)	0.0571 (8)
H7A	0.6398	0.7178	0.7210	0.069*
H7B	0.4912	0.7325	0.7156	0.069*
C8	0.5585 (3)	0.75709 (16)	0.79603 (12)	0.0493 (7)
C9	0.4505 (3)	0.79434 (16)	0.81874 (11)	0.0466 (7)
C10	0.4332 (3)	0.80035 (17)	0.87713 (12)	0.0530 (7)
C11	0.5251 (3)	0.76689 (17)	0.91359 (12)	0.0621 (8)
H11	0.5141	0.7699	0.9530	0.075*
C12	0.6334 (3)	0.72896 (19)	0.89072 (14)	0.0706 (9)
H12	0.6952	0.7064	0.9150	0.085*
C13	0.6505 (3)	0.72439 (17)	0.83255 (14)	0.0649 (9)
H13	0.7239	0.6993	0.8177	0.078*
C14	0.2953 (3)	0.84900 (19)	0.95184 (11)	0.0816 (10)
H14A	0.2140	0.8767	0.9563	0.122*
H14B	0.3612	0.8831	0.9689	0.122*
H14C	0.2928	0.7946	0.9702	0.122*
C15	0.6505 (2)	1.09019 (15)	0.67237 (10)	0.0491 (7)
H15A	0.6634	1.1243	0.7064	0.059*
H15B	0.5924	1.1208	0.6474	0.059*
C16	0.7768 (3)	1.07911 (15)	0.64244 (11)	0.0434 (7)
C17	0.8811 (3)	1.04933 (15)	0.67309 (11)	0.0446 (7)
C18	0.9967 (3)	1.03145 (17)	0.64600 (11)	0.0536 (7)
C19	1.0088 (3)	1.04800 (19)	0.58878 (12)	0.0713 (9)
H19	1.0863	1.0375	0.5705	0.086*
C20	0.9071 (3)	1.08003 (19)	0.55801 (12)	0.0741 (10)
H20	0.9163	1.0914	0.5192	0.089*
C21	0.7921 (3)	1.09514 (16)	0.58479 (12)	0.0615 (8)
H21	0.7237	1.1165	0.5638	0.074*
C22	1.2059 (3)	0.9721 (2)	0.65500 (12)	0.0846 (10)
H22A	1.2626	0.9502	0.6838	0.127*
H22B	1.2457	1.0195	0.6363	0.127*
H22C	1.1883	0.9286	0.6274	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0537 (16)	0.0395 (14)	0.0523 (15)	−0.0008 (12)	0.0054 (13)	−0.0033 (11)
N2	0.0469 (15)	0.0448 (14)	0.0452 (14)	0.0015 (12)	−0.0027 (11)	0.0015 (12)
O1	0.0496 (13)	0.0782 (14)	0.0594 (13)	0.0092 (12)	0.0015 (11)	0.0044 (11)
O2	0.0665 (15)	0.0902 (15)	0.0536 (13)	0.0108 (12)	0.0058 (11)	−0.0026 (12)
O3	0.0457 (13)	0.0683 (12)	0.0462 (12)	0.0048 (11)	0.0029 (9)	0.0050 (10)
O4	0.0449 (13)	0.1012 (16)	0.0627 (13)	0.0104 (12)	0.0079 (11)	−0.0100 (12)
C1	0.0378 (17)	0.0527 (19)	0.0443 (16)	−0.0038 (14)	0.0055 (14)	−0.0055 (15)
C2	0.0323 (16)	0.0504 (17)	0.0421 (16)	−0.0033 (13)	0.0033 (14)	−0.0040 (14)
C3	0.0459 (18)	0.0672 (19)	0.0477 (17)	−0.0066 (15)	−0.0029 (15)	0.0022 (16)
C4	0.055 (2)	0.102 (3)	0.0469 (18)	−0.012 (2)	−0.0022 (15)	0.003 (2)
C5	0.080 (3)	0.096 (3)	0.051 (2)	−0.028 (2)	0.0026 (18)	−0.019 (2)
C6	0.067 (2)	0.0619 (19)	0.0558 (19)	−0.0155 (17)	0.0093 (18)	−0.0101 (17)
C7	0.059 (2)	0.0410 (16)	0.072 (2)	−0.0004 (15)	0.0108 (16)	0.0000 (15)
C8	0.0458 (19)	0.0385 (16)	0.0636 (19)	−0.0048 (15)	0.0064 (17)	0.0065 (15)
C9	0.048 (2)	0.0407 (16)	0.0509 (18)	−0.0022 (15)	−0.0034 (17)	0.0045 (14)
C10	0.047 (2)	0.0532 (18)	0.059 (2)	−0.0049 (16)	−0.0007 (17)	0.0014 (16)
C11	0.061 (2)	0.070 (2)	0.0558 (18)	−0.0108 (18)	−0.0051 (19)	0.0066 (17)
C12	0.056 (2)	0.080 (2)	0.076 (2)	−0.0001 (18)	−0.0115 (19)	0.0193 (19)
C13	0.050 (2)	0.060 (2)	0.085 (2)	0.0046 (16)	0.0033 (19)	0.0113 (18)
C14	0.089 (3)	0.098 (3)	0.059 (2)	0.010 (2)	0.0088 (18)	−0.0121 (19)
C15	0.057 (2)	0.0383 (16)	0.0518 (16)	0.0008 (15)	−0.0050 (15)	0.0010 (14)
C16	0.0483 (18)	0.0363 (15)	0.0456 (16)	−0.0060 (14)	0.0047 (15)	0.0006 (13)
C17	0.053 (2)	0.0412 (16)	0.0399 (16)	−0.0052 (14)	0.0068 (15)	−0.0047 (13)
C18	0.0483 (19)	0.0637 (19)	0.0488 (17)	−0.0034 (16)	0.0086 (17)	−0.0065 (16)
C19	0.060 (2)	0.094 (2)	0.060 (2)	−0.011 (2)	0.0150 (19)	−0.0087 (19)
C20	0.083 (3)	0.094 (2)	0.0453 (18)	−0.020 (2)	0.014 (2)	0.0037 (18)
C21	0.068 (2)	0.0632 (19)	0.0531 (19)	−0.0116 (18)	−0.0052 (17)	0.0103 (16)
C22	0.051 (2)	0.117 (3)	0.085 (2)	0.009 (2)	0.0109 (19)	−0.022 (2)

Geometric parameters (Å, º) top

N1—C1	1.412 (3)	C8—C9	1.377 (3)
N1—C7	1.479 (3)	C8—C13	1.384 (3)
N1—H1	0.89 (2)	C9—C10	1.381 (3)
N2—C2	1.413 (3)	C10—C11	1.387 (3)
N2—C15	1.472 (3)	C11—C12	1.386 (4)
N2—H2	0.91 (2)	C11—H11	0.9300
O1—C9	1.358 (3)	C12—C13	1.375 (4)
O1—H1A	0.87 (3)	C12—H12	0.9300
O2—C10	1.362 (3)	C13—H13	0.9300
O2—C14	1.405 (3)	C14—H14A	0.9600
O3—C17	1.364 (3)	C14—H14B	0.9600
O3—H3	0.88 (3)	C14—H14C	0.9600
O4—C18	1.366 (3)	C15—C16	1.503 (3)
O4—C22	1.423 (3)	C15—H15A	0.9700
C1—C6	1.379 (3)	C15—H15B	0.9700
C1—C2	1.406 (3)	C16—C21	1.382 (3)
C2—C3	1.370 (3)	C16—C17	1.385 (3)
C3—C4	1.381 (3)	C17—C18	1.392 (3)
C3—H3A	0.9300	C18—C19	1.370 (3)
C4—C5	1.371 (4)	C19—C20	1.378 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.379 (3)	C20—C21	1.374 (4)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.502 (3)	C22—H22A	0.9600
C7—H7A	0.9700	C22—H22B	0.9600
C7—H7B	0.9700	C22—H22C	0.9600

C1—N1—C7	119.9 (2)	C12—C11—H11	120.3
C1—N1—H1	108.8 (15)	C10—C11—H11	120.3
C7—N1—H1	106.4 (15)	C13—C12—C11	120.7 (3)
C2—N2—C15	119.0 (2)	C13—C12—H12	119.6
C2—N2—H2	112.0 (14)	C11—C12—H12	119.6
C15—N2—H2	108.5 (15)	C12—C13—C8	120.1 (3)
C9—O1—H1A	114.3 (19)	C12—C13—H13	119.9
C10—O2—C14	119.5 (2)	C8—C13—H13	119.9
C17—O3—H3	113.7 (18)	O2—C14—H14A	109.5
C18—O4—C22	117.5 (2)	O2—C14—H14B	109.5
C6—C1—C2	119.3 (2)	H14A—C14—H14B	109.5
C6—C1—N1	123.9 (2)	O2—C14—H14C	109.5
C2—C1—N1	116.7 (2)	H14A—C14—H14C	109.5
C3—C2—C1	119.2 (2)	H14B—C14—H14C	109.5
C3—C2—N2	123.3 (2)	N2—C15—C16	113.2 (2)
C1—C2—N2	117.4 (2)	N2—C15—H15A	108.9
C2—C3—C4	120.9 (3)	C16—C15—H15A	108.9
C2—C3—H3A	119.5	N2—C15—H15B	108.9
C4—C3—H3A	119.5	C16—C15—H15B	108.9
C5—C4—C3	119.9 (3)	H15A—C15—H15B	107.7
C5—C4—H4	120.0	C21—C16—C17	118.5 (3)
C3—C4—H4	120.0	C21—C16—C15	122.4 (3)
C4—C5—C6	120.0 (3)	C17—C16—C15	119.1 (2)
C4—C5—H5	120.0	O3—C17—C16	118.1 (2)
C6—C5—H5	120.0	O3—C17—C18	121.0 (3)
C5—C6—C1	120.5 (3)	C16—C17—C18	120.9 (2)
C5—C6—H6	119.7	O4—C18—C19	126.2 (3)
C1—C6—H6	119.7	O4—C18—C17	114.7 (2)
N1—C7—C8	109.0 (2)	C19—C18—C17	119.1 (3)
N1—C7—H7A	109.9	C18—C19—C20	120.7 (3)
C8—C7—H7A	109.9	C18—C19—H19	119.7
N1—C7—H7B	109.9	C20—C19—H19	119.7
C8—C7—H7B	109.9	C21—C20—C19	119.8 (3)
H7A—C7—H7B	108.3	C21—C20—H20	120.1
C9—C8—C13	119.2 (3)	C19—C20—H20	120.1
C9—C8—C7	117.3 (3)	C20—C21—C16	121.0 (3)
C13—C8—C7	123.5 (3)	C20—C21—H21	119.5
O1—C9—C8	117.5 (2)	C16—C21—H21	119.5
O1—C9—C10	121.4 (3)	O4—C22—H22A	109.5
C8—C9—C10	121.2 (3)	O4—C22—H22B	109.5
O2—C10—C9	114.7 (3)	H22A—C22—H22B	109.5
O2—C10—C11	125.8 (3)	O4—C22—H22C	109.5
C9—C10—C11	119.5 (3)	H22A—C22—H22C	109.5
C12—C11—C10	119.3 (3)	H22B—C22—H22C	109.5

C7—N1—C1—C6	−15.2 (4)	C8—C9—C10—C11	−1.2 (4)
C7—N1—C1—C2	167.2 (2)	O2—C10—C11—C12	179.0 (2)
C6—C1—C2—C3	1.8 (4)	C9—C10—C11—C12	0.8 (4)
N1—C1—C2—C3	179.6 (2)	C10—C11—C12—C13	0.1 (4)
C6—C1—C2—N2	177.9 (2)	C11—C12—C13—C8	−0.6 (4)
N1—C1—C2—N2	−4.4 (3)	C9—C8—C13—C12	0.2 (4)
C15—N2—C2—C3	−31.7 (3)	C7—C8—C13—C12	−180.0 (3)
C15—N2—C2—C1	152.4 (2)	C2—N2—C15—C16	−68.3 (3)
C1—C2—C3—C4	−0.1 (4)	N2—C15—C16—C21	109.0 (3)
N2—C2—C3—C4	−175.9 (2)	N2—C15—C16—C17	−69.0 (3)
C2—C3—C4—C5	−1.4 (4)	C21—C16—C17—O3	178.0 (2)
C3—C4—C5—C6	1.0 (5)	C15—C16—C17—O3	−4.0 (3)
C4—C5—C6—C1	0.8 (4)	C21—C16—C17—C18	−3.5 (4)
C2—C1—C6—C5	−2.2 (4)	C15—C16—C17—C18	174.6 (2)
N1—C1—C6—C5	−179.7 (2)	C22—O4—C18—C19	−5.9 (4)
C1—N1—C7—C8	−145.5 (2)	C22—O4—C18—C17	174.6 (2)
N1—C7—C8—C9	70.7 (3)	O3—C17—C18—O4	1.5 (4)
N1—C7—C8—C13	−109.1 (3)	C16—C17—C18—O4	−177.0 (2)
C13—C8—C9—O1	−179.3 (2)	O3—C17—C18—C19	−178.0 (2)
C7—C8—C9—O1	0.9 (3)	C16—C17—C18—C19	3.5 (4)
C13—C8—C9—C10	0.7 (4)	O4—C18—C19—C20	179.0 (3)
C7—C8—C9—C10	−179.1 (2)	C17—C18—C19—C20	−1.5 (4)
C14—O2—C10—C9	−178.9 (2)	C18—C19—C20—C21	−0.4 (5)
C14—O2—C10—C11	2.8 (4)	C19—C20—C21—C16	0.3 (4)
O1—C9—C10—O2	0.4 (4)	C17—C16—C21—C20	1.6 (4)
C8—C9—C10—O2	−179.6 (2)	C15—C16—C21—C20	−176.4 (2)
O1—C9—C10—C11	178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.87 (3)	2.04 (3)	2.821 (3)	149 (3)
O3—H3···N2ⁱⁱ	0.88 (3)	2.18 (3)	3.038 (3)	166 (2)
N2—H2···O4ⁱ	0.91 (2)	2.55 (2)	3.052 (3)	115.5 (17)
N1—H1···O1	0.89 (2)	2.50 (2)	2.940 (3)	111.3 (18)
N2—H2···O3	0.91 (2)	2.50 (2)	3.065 (3)	120.1 (18)
N2—H2···N1	0.91 (2)	2.28 (2)	2.694 (3)	107.4 (17)
N1—H1···N2	0.89 (2)	2.40 (2)	2.694 (3)	99.6 (16)
O1—H1A···O2	0.87 (3)	2.29 (3)	2.659 (2)	106 (2)
O3—H3···O4	0.88 (3)	2.27 (3)	2.665 (3)	107 (2)
C7—H7B···O1	0.97	2.52	2.696 (3)	90

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂O₄
M_r	380.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	10.4331 (14), 15.7674 (16), 23.398 (2)
V (Å³)	3849.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.21 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	14963, 3383, 1530
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.096, 0.81
No. of reflections	3383
No. of parameters	265
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.17

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.