Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050477/bt2535sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050477/bt2535Isup2.hkl |
CCDC reference: 667393
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.054
- wR factor = 0.149
- Data-to-parameter ratio = 20.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.802 1.000 Tmin(prime) and Tmax expected: 0.936 0.958 RR(prime) = 0.821 Please check that your absorption correction is appropriate. DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.719 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.28 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.72 e/A PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.958 Tmax scaled 0.958 Tmin scaled 0.768
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 4 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
For related structures, see: Crass et al. (1996); Anjum et al. (2005). For related literature, see: Ravindra et al. (2006); Glidewell et al. (2005); Munn & Ironside (1993).
Aniline [1.395 (9) g, 0.015 mole] and p-nitrophenylsuccinamic acid [2.381 (1) g, 0.01 mole] were mixed in a test tube and the mixture was heated to 140° for 3 h. After cooling the solid residue was washed with dilute HCl to remove excess aniline and dried. Purification was carried out by successive recrystallization from a dimethylformamide (DMF) solution. Crystal growth was achieved by the slow evaporation of a DMF solution of (I). Analysis found: C 61.29, H 4.52, N 13.38; C16H15N3O4 requires: C 61.33, H 4.78, N 13.41.
The amide hydrogen atoms (H1A & H2B) were located in a difference Fourier map and along with all other H atoms were placed in their calculated positions and then refined using the riding model with N—H = 0.88 Å and C—H = 0.95 to 0.99 Å, and with Uiso(H) = 1.17–1.22Ueq(C,N). The maximum residual electron density peaks of 0.72 and -0.32 e Å3, were located at 0.68 from C13 and 0.50 Å from N3. Owing to the poor diffraction quality of the crystal, the range of Tmax to Tmin is large (0.82).
Organic nonlinear optical (NLO) materials are of increasing interest due to their large second harmonic conversion efficiency, ultra fast response, high laser damage resistance, and flexibility they offer to tune the nonlinear optical properties through structure modification [Munn & Ironside (1993)]. Due to the presence of inversion symmetry in (I), the second harmonic response is zero. However, it exhibits third order nonlinear optical properties (nonlinear absorption and nonlinear refraction). The detailed measurement on the third order nonlinear properties of (I) has not yet performed. In order to further understand the structure-property relationship of these compounds, the title compound (I) has been synthesized and its crystal structure is reported.
The geometric parameters for (I) are normal. The C8—C9 bond length of 1.5246 (15) Å is in good agreement with the three isomeric N-(p-chlorophenyl)succinimides [Glidewell et al. (2005); C8—C9 = 1.5276 (19), 1.518 (3) and 1.524 (5) Å] (Fig. 1). The dihedral angle between the two benzene rings [C1—C6 and C11—C16] is 16.66 (6)°. The molecule crystallizes in a cetrosymmetric space group and hence does not exhibit second order nonlinear optical properties. The angle between the mean plane of the 4-nitrophenyl group and the adjacent N1–C7–O1 group is 26.2 (8)° while the angle between the mean plane of the benzene ring and its adjacent N2–C10–O2 group is 40.8 (5)°. The dihedral angle between the two N–C–O groups is 5.2 (3)°. The mean plane through the succinic acid fragment (C7—C10) makes the dihedral angle of 3.26 (9)° and 14.60 (9)° with the C1—C6 and C11—C16 benzene rings, respectively. Crystal packing is stabilized by intermolecular N—H—O interactions which link the molecules into chains along the b axis in the bc plane with the phenyl rings arranged oblique to this plane (Fig. 2).
For related structures, see: Crass et al. (1996); Anjum et al. (2005). For related literature, see: Ravindra et al. (2006); Glidewell et al. (2005); Munn & Ironside (1993).
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2000); software used to prepare material for publication: SHELXTL (Bruker 2000).
C16H15N3O4 | Z = 2 |
Mr = 313.31 | F(000) = 328 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.7585 (4) Å | Cell parameters from 6328 reflections |
b = 9.8447 (8) Å | θ = 2.4–30.5° |
c = 12.9961 (10) Å | µ = 0.11 mm−1 |
α = 79.216 (1)° | T = 100 K |
β = 79.014 (1)° | Block, colorless |
γ = 83.779 (1)° | 0.60 × 0.53 × 0.40 mm |
V = 708.46 (9) Å3 |
Bruker SMART CCD area detector diffractometer | 4260 independent reflections |
Radiation source: fine-focus sealed tube | 3904 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 30.5°, θmin = 1.6° |
Absorption correction: multi-scan SADABS (Sheldrick, 2004) | h = −8→8 |
Tmin = 0.802, Tmax = 1.000 | k = −14→14 |
8553 measured reflections | l = −17→18 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0918P)2 + 0.2598P] where P = (Fo2 + 2Fc2)/3 |
4260 reflections | (Δ/σ)max = 0.003 |
208 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C16H15N3O4 | γ = 83.779 (1)° |
Mr = 313.31 | V = 708.46 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7585 (4) Å | Mo Kα radiation |
b = 9.8447 (8) Å | µ = 0.11 mm−1 |
c = 12.9961 (10) Å | T = 100 K |
α = 79.216 (1)° | 0.60 × 0.53 × 0.40 mm |
β = 79.014 (1)° |
Bruker SMART CCD area detector diffractometer | 4260 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 2004) | 3904 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 1.000 | Rint = 0.014 |
8553 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.72 e Å−3 |
4260 reflections | Δρmin = −0.32 e Å−3 |
208 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 | ||
O1 | 0.20220 (15) | 0.59779 (8) | 0.11503 (7) | 0.0216 (2) | |
O2 | 0.85535 (16) | 0.89058 (8) | −0.09865 (8) | 0.0238 (2) | |
O31 | −0.94624 (17) | 0.83821 (11) | 0.42542 (8) | 0.0303 (2) | |
O32 | −0.83201 (19) | 0.62538 (11) | 0.48486 (9) | 0.0339 (2) | |
N1 | 0.06558 (16) | 0.81592 (9) | 0.14504 (8) | 0.01558 (19) | |
H1A | 0.1019 | 0.9028 | 0.1300 | 0.019* | |
N2 | 0.97801 (16) | 0.67817 (9) | −0.14277 (7) | 0.01529 (19) | |
H2B | 0.9512 | 0.5897 | −0.1272 | 0.018* | |
N3 | −0.79896 (19) | 0.73754 (12) | 0.42692 (9) | 0.0237 (2) | |
C1 | −0.14639 (18) | 0.78803 (10) | 0.21684 (8) | 0.0142 (2) | |
C2 | −0.3242 (2) | 0.89650 (11) | 0.21885 (9) | 0.0192 (2) | |
H2A | −0.2980 | 0.9824 | 0.1725 | 0.023* | |
C3 | −0.5377 (2) | 0.87974 (13) | 0.28773 (10) | 0.0215 (2) | |
H3A | −0.6589 | 0.9533 | 0.2893 | 0.026* | |
C4 | −0.5715 (2) | 0.75360 (12) | 0.35439 (9) | 0.0184 (2) | |
C5 | −0.3970 (2) | 0.64476 (12) | 0.35496 (9) | 0.0193 (2) | |
H5A | −0.4238 | 0.5596 | 0.4021 | 0.023* | |
C6 | −0.1823 (2) | 0.66201 (11) | 0.28562 (9) | 0.0175 (2) | |
H6A | −0.0608 | 0.5886 | 0.2850 | 0.021* | |
C7 | 0.22059 (18) | 0.72342 (11) | 0.09634 (8) | 0.0147 (2) | |
C8 | 0.41412 (19) | 0.79024 (11) | 0.01248 (9) | 0.0165 (2) | |
H8A | 0.4492 | 0.8769 | 0.0327 | 0.020* | |
H8B | 0.3566 | 0.8150 | −0.0562 | 0.020* | |
C9 | 0.64177 (19) | 0.69581 (10) | −0.00172 (8) | 0.0152 (2) | |
H9A | 0.7002 | 0.6710 | 0.0668 | 0.018* | |
H9B | 0.6077 | 0.6092 | −0.0224 | 0.018* | |
C10 | 0.83239 (19) | 0.76554 (11) | −0.08602 (8) | 0.0151 (2) | |
C11 | 1.17126 (19) | 0.71785 (11) | −0.22565 (8) | 0.0145 (2) | |
C12 | 1.1442 (2) | 0.83097 (12) | −0.30570 (9) | 0.0190 (2) | |
H12A | 0.9966 | 0.8846 | −0.3048 | 0.023* | |
C13 | 1.3342 (2) | 0.86508 (13) | −0.38702 (10) | 0.0230 (2) | |
H13A | 1.3166 | 0.9433 | −0.4409 | 0.028* | |
C14 | 1.5494 (2) | 0.78587 (13) | −0.39017 (10) | 0.0236 (3) | |
H14A | 1.6781 | 0.8092 | −0.4463 | 0.028* | |
C15 | 1.5752 (2) | 0.67233 (13) | −0.31067 (10) | 0.0233 (2) | |
H15A | 1.7217 | 0.6175 | −0.3127 | 0.028* | |
C16 | 1.3867 (2) | 0.63844 (12) | −0.22772 (9) | 0.0188 (2) | |
H16A | 1.4054 | 0.5615 | −0.1729 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0215 (4) | 0.0110 (4) | 0.0287 (4) | −0.0031 (3) | 0.0062 (3) | −0.0044 (3) |
O2 | 0.0255 (4) | 0.0119 (4) | 0.0305 (5) | −0.0060 (3) | 0.0085 (3) | −0.0058 (3) |
O31 | 0.0197 (4) | 0.0355 (5) | 0.0326 (5) | 0.0023 (4) | 0.0018 (4) | −0.0065 (4) |
O32 | 0.0299 (5) | 0.0304 (5) | 0.0359 (6) | −0.0092 (4) | 0.0064 (4) | −0.0003 (4) |
N1 | 0.0159 (4) | 0.0096 (4) | 0.0194 (4) | −0.0019 (3) | 0.0021 (3) | −0.0026 (3) |
N2 | 0.0158 (4) | 0.0104 (4) | 0.0176 (4) | −0.0025 (3) | 0.0025 (3) | −0.0018 (3) |
N3 | 0.0194 (5) | 0.0279 (5) | 0.0232 (5) | −0.0049 (4) | 0.0006 (4) | −0.0053 (4) |
C1 | 0.0143 (4) | 0.0130 (4) | 0.0153 (5) | −0.0020 (3) | −0.0005 (3) | −0.0037 (3) |
C2 | 0.0192 (5) | 0.0141 (5) | 0.0215 (5) | 0.0014 (4) | −0.0006 (4) | −0.0005 (4) |
C3 | 0.0172 (5) | 0.0211 (5) | 0.0241 (5) | 0.0038 (4) | −0.0012 (4) | −0.0042 (4) |
C4 | 0.0156 (5) | 0.0223 (5) | 0.0174 (5) | −0.0036 (4) | 0.0001 (4) | −0.0056 (4) |
C5 | 0.0209 (5) | 0.0176 (5) | 0.0175 (5) | −0.0034 (4) | 0.0014 (4) | −0.0019 (4) |
C6 | 0.0186 (5) | 0.0141 (4) | 0.0176 (5) | 0.0002 (4) | 0.0002 (4) | −0.0014 (4) |
C7 | 0.0142 (4) | 0.0122 (4) | 0.0168 (5) | −0.0019 (3) | 0.0002 (3) | −0.0029 (3) |
C8 | 0.0166 (5) | 0.0118 (4) | 0.0187 (5) | −0.0021 (3) | 0.0023 (4) | −0.0012 (3) |
C9 | 0.0153 (4) | 0.0118 (4) | 0.0165 (5) | −0.0028 (3) | 0.0019 (4) | −0.0013 (3) |
C10 | 0.0149 (4) | 0.0130 (4) | 0.0165 (5) | −0.0025 (3) | 0.0004 (4) | −0.0029 (3) |
C11 | 0.0143 (4) | 0.0132 (4) | 0.0157 (5) | −0.0029 (3) | 0.0002 (3) | −0.0036 (3) |
C12 | 0.0185 (5) | 0.0174 (5) | 0.0186 (5) | −0.0013 (4) | 0.0000 (4) | −0.0001 (4) |
C13 | 0.0251 (6) | 0.0229 (5) | 0.0182 (5) | −0.0055 (4) | 0.0016 (4) | 0.0003 (4) |
C14 | 0.0193 (5) | 0.0297 (6) | 0.0211 (5) | −0.0073 (4) | 0.0044 (4) | −0.0073 (4) |
C15 | 0.0150 (5) | 0.0280 (6) | 0.0268 (6) | 0.0004 (4) | −0.0003 (4) | −0.0091 (5) |
C16 | 0.0171 (5) | 0.0184 (5) | 0.0201 (5) | 0.0013 (4) | −0.0027 (4) | −0.0037 (4) |
O1—C7 | 1.2273 (13) | C6—H6A | 0.9500 |
O2—C10 | 1.2293 (13) | C7—C8 | 1.5133 (14) |
O31—N3 | 1.2324 (14) | C8—C9 | 1.5246 (15) |
O32—N3 | 1.2256 (15) | C8—H8A | 0.9900 |
N1—C7 | 1.3605 (13) | C8—H8B | 0.9900 |
N1—C1 | 1.4067 (13) | C9—C10 | 1.5166 (14) |
N1—H1A | 0.8800 | C9—H9A | 0.9900 |
N2—C10 | 1.3536 (13) | C9—H9B | 0.9900 |
N2—C11 | 1.4252 (13) | C11—C16 | 1.3913 (15) |
N2—H2B | 0.8800 | C11—C12 | 1.3918 (15) |
N3—C4 | 1.4655 (15) | C12—C13 | 1.3901 (15) |
C1—C6 | 1.3968 (15) | C12—H12A | 0.9500 |
C1—C2 | 1.3973 (14) | C13—C14 | 1.3889 (18) |
C2—C3 | 1.3820 (16) | C13—H13A | 0.9500 |
C2—H2A | 0.9500 | C14—C15 | 1.3890 (18) |
C3—C4 | 1.3842 (17) | C14—H14A | 0.9500 |
C3—H3A | 0.9500 | C15—C16 | 1.3963 (16) |
C4—C5 | 1.3873 (16) | C15—H15A | 0.9500 |
C5—C6 | 1.3903 (15) | C16—H16A | 0.9500 |
C5—H5A | 0.9500 | ||
C7—N1—C1 | 127.19 (9) | C9—C8—H8A | 109.1 |
C7—N1—H1A | 116.4 | C7—C8—H8B | 109.1 |
C1—N1—H1A | 116.4 | C9—C8—H8B | 109.1 |
C10—N2—C11 | 125.28 (9) | H8A—C8—H8B | 107.8 |
C10—N2—H2B | 117.4 | C10—C9—C8 | 111.42 (9) |
C11—N2—H2B | 117.4 | C10—C9—H9A | 109.3 |
O32—N3—O31 | 123.96 (11) | C8—C9—H9A | 109.3 |
O32—N3—C4 | 118.41 (10) | C10—C9—H9B | 109.3 |
O31—N3—C4 | 117.63 (10) | C8—C9—H9B | 109.3 |
C6—C1—C2 | 120.11 (10) | H9A—C9—H9B | 108.0 |
C6—C1—N1 | 123.70 (9) | O2—C10—N2 | 123.39 (10) |
C2—C1—N1 | 116.17 (9) | O2—C10—C9 | 122.10 (9) |
C3—C2—C1 | 120.47 (10) | N2—C10—C9 | 114.47 (9) |
C3—C2—H2A | 119.8 | C16—C11—C12 | 120.11 (10) |
C1—C2—H2A | 119.8 | C16—C11—N2 | 118.88 (10) |
C2—C3—C4 | 118.67 (10) | C12—C11—N2 | 120.97 (10) |
C2—C3—H3A | 120.7 | C13—C12—C11 | 119.69 (11) |
C4—C3—H3A | 120.7 | C13—C12—H12A | 120.2 |
C3—C4—C5 | 122.05 (10) | C11—C12—H12A | 120.2 |
C3—C4—N3 | 117.98 (10) | C14—C13—C12 | 120.62 (11) |
C5—C4—N3 | 119.97 (10) | C14—C13—H13A | 119.7 |
C4—C5—C6 | 119.13 (10) | C12—C13—H13A | 119.7 |
C4—C5—H5A | 120.4 | C15—C14—C13 | 119.55 (11) |
C6—C5—H5A | 120.4 | C15—C14—H14A | 120.2 |
C5—C6—C1 | 119.56 (10) | C13—C14—H14A | 120.2 |
C5—C6—H6A | 120.2 | C14—C15—C16 | 120.30 (11) |
C1—C6—H6A | 120.2 | C14—C15—H15A | 119.9 |
O1—C7—N1 | 123.76 (10) | C16—C15—H15A | 119.9 |
O1—C7—C8 | 122.49 (9) | C11—C16—C15 | 119.73 (11) |
N1—C7—C8 | 113.69 (9) | C11—C16—H16A | 120.1 |
C7—C8—C9 | 112.61 (9) | C15—C16—H16A | 120.1 |
C7—C8—H8A | 109.1 | ||
C7—N1—C1—C6 | 30.18 (17) | O1—C7—C8—C9 | −30.73 (15) |
C7—N1—C1—C2 | −151.52 (11) | N1—C7—C8—C9 | 151.83 (10) |
C6—C1—C2—C3 | −0.80 (17) | C7—C8—C9—C10 | −179.91 (9) |
N1—C1—C2—C3 | −179.16 (10) | C11—N2—C10—O2 | −1.76 (18) |
C1—C2—C3—C4 | −0.03 (18) | C11—N2—C10—C9 | −179.55 (10) |
C2—C3—C4—C5 | 0.83 (18) | C8—C9—C10—O2 | 35.54 (15) |
C2—C3—C4—N3 | −179.99 (10) | C8—C9—C10—N2 | −146.63 (10) |
O32—N3—C4—C3 | 178.70 (12) | C10—N2—C11—C16 | 135.14 (12) |
O31—N3—C4—C3 | −0.99 (17) | C10—N2—C11—C12 | −47.19 (16) |
O32—N3—C4—C5 | −2.09 (17) | C16—C11—C12—C13 | −0.71 (17) |
O31—N3—C4—C5 | 178.21 (11) | N2—C11—C12—C13 | −178.36 (10) |
C3—C4—C5—C6 | −0.79 (18) | C11—C12—C13—C14 | 1.16 (18) |
N3—C4—C5—C6 | −179.96 (10) | C12—C13—C14—C15 | −0.60 (19) |
C4—C5—C6—C1 | −0.06 (17) | C13—C14—C15—C16 | −0.41 (19) |
C2—C1—C6—C5 | 0.83 (17) | C12—C11—C16—C15 | −0.28 (17) |
N1—C1—C6—C5 | 179.07 (10) | N2—C11—C16—C15 | 177.41 (10) |
C1—N1—C7—O1 | −5.20 (18) | C14—C15—C16—C11 | 0.85 (18) |
C1—N1—C7—C8 | 172.20 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 2.03 | 2.9066 (12) | 173 |
N2—H2B···O1ii | 0.88 | 2.10 | 2.9478 (12) | 162 |
C6—H6A···O1 | 0.95 | 2.42 | 2.9271 (15) | 113 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H15N3O4 |
Mr | 313.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 5.7585 (4), 9.8447 (8), 12.9961 (10) |
α, β, γ (°) | 79.216 (1), 79.014 (1), 83.779 (1) |
V (Å3) | 708.46 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.60 × 0.53 × 0.40 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector |
Absorption correction | Multi-scan SADABS (Sheldrick, 2004) |
Tmin, Tmax | 0.802, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8553, 4260, 3904 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.149, 1.05 |
No. of reflections | 4260 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.32 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.88 | 2.03 | 2.9066 (12) | 173.3 |
N2—H2B···O1ii | 0.88 | 2.10 | 2.9478 (12) | 162.0 |
C6—H6A···O1 | 0.95 | 2.42 | 2.9271 (15) | 113 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z. |
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Organic nonlinear optical (NLO) materials are of increasing interest due to their large second harmonic conversion efficiency, ultra fast response, high laser damage resistance, and flexibility they offer to tune the nonlinear optical properties through structure modification [Munn & Ironside (1993)]. Due to the presence of inversion symmetry in (I), the second harmonic response is zero. However, it exhibits third order nonlinear optical properties (nonlinear absorption and nonlinear refraction). The detailed measurement on the third order nonlinear properties of (I) has not yet performed. In order to further understand the structure-property relationship of these compounds, the title compound (I) has been synthesized and its crystal structure is reported.
The geometric parameters for (I) are normal. The C8—C9 bond length of 1.5246 (15) Å is in good agreement with the three isomeric N-(p-chlorophenyl)succinimides [Glidewell et al. (2005); C8—C9 = 1.5276 (19), 1.518 (3) and 1.524 (5) Å] (Fig. 1). The dihedral angle between the two benzene rings [C1—C6 and C11—C16] is 16.66 (6)°. The molecule crystallizes in a cetrosymmetric space group and hence does not exhibit second order nonlinear optical properties. The angle between the mean plane of the 4-nitrophenyl group and the adjacent N1–C7–O1 group is 26.2 (8)° while the angle between the mean plane of the benzene ring and its adjacent N2–C10–O2 group is 40.8 (5)°. The dihedral angle between the two N–C–O groups is 5.2 (3)°. The mean plane through the succinic acid fragment (C7—C10) makes the dihedral angle of 3.26 (9)° and 14.60 (9)° with the C1—C6 and C11—C16 benzene rings, respectively. Crystal packing is stabilized by intermolecular N—H—O interactions which link the molecules into chains along the b axis in the bc plane with the phenyl rings arranged oblique to this plane (Fig. 2).