Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027778/at2321sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027778/at2321Isup2.hkl |
CCDC reference: 649513
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
For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).
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.
H atoms bonded to O and N atoms were found a difference Fourier map and refined freely. All other H atoms were place in geometrically calculated positions and allowed to ride on their respective parent atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), 0.97 Å (methylene), Uiso(H) = 1.2 (Caryl, methylene) or 1.5 Ueq(Cmethyl).
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).
For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Liu et al. (2007); Xia et al. (2007).
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.
C22H24N2O4 | F(000) = 1616 |
Mr = 380.43 | Dx = 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 |
Siemens SMART 1000 CCD area-detector diffractometer | 3383 independent reflections |
Radiation source: fine-focus sealed tube | 1530 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.966, Tmax = 0.991 | k = −18→9 |
14963 measured reflections | l = −27→27 |
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(Fo2) + (0.0315P)2] where P = (Fo2 + 2Fc2)/3 |
3383 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C22H24N2O4 | V = 3849.1 (7) Å3 |
Mr = 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 |
Siemens SMART 1000 CCD area-detector diffractometer | 3383 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1530 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.991 | Rint = 0.091 |
14963 measured reflections |
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 | Δρmax = 0.12 e Å−3 |
3383 reflections | Δρmin = −0.17 e Å−3 |
265 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.966, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14963, 3383, 1530 |
Rint | 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 |
Δρmax, Δρmin (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.
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) | 90.0 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2. |
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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).