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The title compound, C18H24N2O4, is an amino­naphtho­quinone derivative that exhibits a large third-order non-linear optical susceptibility. The centrosymmetric naphtho­quinone moieties are connected by bifurcated N—H...O hydrogen bonds to form a ribbon structure along [1\overline10]. The mol­ecules are stacked along the c axis, with overlap occurring only at the periphery of the naphtho­quinone skeleton.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019792/ob6296sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019792/ob6296Isup2.hkl
Contains datablock I

CCDC reference: 225722

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.117
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.19 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1429 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1584 Completeness (_total/calc) 90.21% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90 PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl .... P -1 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 = 5.84 su PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H1 = 1.06 Ang.
1 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C18H24N2O4Z = 1
Mr = 332.40F(000) = 178.0
Triclinic, P1Dx = 1.275 Mg m3
Hall symbol: P -1Cu Kα radiation, λ = 1.5418 Å
a = 5.2257 (7) ÅCell parameters from 3066 reflections
b = 6.8930 (9) Åθ = 3.7–68.1°
c = 12.162 (1) ŵ = 0.74 mm1
α = 97.72 (1)°T = 93 K
β = 91.93 (1)°Platelet, black
γ = 93.66 (1)°0.35 × 0.20 × 0.03 mm
V = 432.83 (9) Å3
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
775 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.038
48 frames, delta ω = 15 deg scansθmax = 68.2°
Absorption correction: multi-scan
(Higashi, 1995)
h = 66
Tmin = 0.738, Tmax = 0.978k = 88
3858 measured reflectionsl = 1414
1429 independent reflections
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.05[Max(Fo2,0) + 2Fc2]/3)2]
wR(F2) = 0.117(Δ/σ)max = 0.016
S = 1.06Δρmax = 0.26 e Å3
1421 reflectionsΔρmin = 0.31 e Å3
112 parameters
Special details top

Refinement. Refinement using reflections with F2 > -3.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1064 (3)0.7748 (2)0.9472 (1)0.0563 (5)
O20.9064 (3)0.5406 (2)1.1846 (1)0.0604 (5)
N10.3045 (3)1.0093 (3)1.1258 (1)0.0515 (5)
C10.7098 (4)0.5954 (3)1.1259 (2)0.0466 (6)
C20.6123 (4)0.7753 (3)1.1603 (2)0.0506 (7)
C30.4082 (4)0.8379 (3)1.1003 (2)0.0463 (6)
C40.2937 (4)0.7116 (3)1.0013 (2)0.0455 (6)
C50.3957 (3)0.5312 (3)0.9694 (2)0.0418 (6)
C60.3796 (4)1.1551 (3)1.2203 (2)0.0536 (7)
C70.2453 (5)1.1212 (3)1.3246 (2)0.0681 (8)
C80.3248 (6)1.2774 (4)1.4211 (2)0.097 (1)
C90.2008 (7)1.2514 (5)1.5269 (2)0.141 (1)
H10.93610.40431.13690.1101*
H20.68460.85591.22480.0607*
H30.16921.03811.07770.0618*
H40.55931.15341.23440.0643*
H50.34111.28021.20220.0643*
H60.28580.99731.34380.0818*
H70.06541.12121.31070.0818*
H80.50531.27761.43360.1166*
H90.28311.40061.40120.1166*
H100.24701.13171.55020.1688*
H110.01971.24791.51580.1688*
H120.25651.35771.58220.1688*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0558 (10)0.055 (1)0.0578 (9)0.0151 (8)0.0072 (8)0.0029 (8)
O20.061 (1)0.059 (1)0.0589 (10)0.0158 (8)0.0146 (8)0.0021 (8)
N10.059 (1)0.045 (1)0.049 (1)0.0101 (9)0.0041 (9)0.0021 (8)
C10.048 (1)0.044 (1)0.047 (1)0.005 (1)0.001 (1)0.005 (1)
C20.057 (1)0.047 (1)0.046 (1)0.003 (1)0.001 (1)0.001 (1)
C30.051 (1)0.041 (1)0.047 (1)0.004 (1)0.008 (1)0.003 (1)
C40.045 (1)0.046 (1)0.045 (1)0.002 (1)0.0043 (10)0.004 (1)
C50.042 (1)0.039 (1)0.044 (1)0.005 (1)0.0027 (9)0.0044 (9)
C60.058 (1)0.046 (1)0.054 (1)0.006 (1)0.001 (1)0.001 (1)
C70.077 (2)0.064 (2)0.059 (1)0.004 (1)0.007 (1)0.003 (1)
C80.126 (2)0.095 (2)0.059 (2)0.024 (2)0.013 (2)0.018 (2)
C90.196 (4)0.144 (3)0.067 (2)0.050 (3)0.030 (2)0.019 (2)
Geometric parameters (Å, º) top
O1—C41.292 (2)C6—C71.509 (3)
O2—C11.334 (2)C6—H40.950
O2—H11.059C6—H50.950
N1—C31.334 (2)C7—C81.509 (3)
N1—C61.447 (3)C7—H60.950
N1—H30.950C7—H70.950
C1—C21.388 (3)C8—C91.487 (4)
C1—C5i1.426 (3)C8—H80.950
C2—C31.395 (3)C8—H90.950
C2—H20.950C9—H100.951
C3—C41.474 (3)C9—H110.950
C4—C51.396 (3)C9—H120.950
C5—C5i1.421 (4)
O1···N1ii2.872 (2)N1···H1vii3.424
O1···C6ii3.302 (3)N1···C3iv3.433 (3)
O1···C1iii3.354 (2)C1···C4vi3.546 (3)
O1···O1ii3.463 (3)C4···H1iii3.367
O1···C6iv3.473 (3)C4···C6iv3.434 (3)
O1···C5v3.523 (2)C5···H1iii3.350
O1···N1iv3.526 (2)C5···C6iv3.546 (3)
O2···C4vi3.341 (2)C6···H1vii3.189
O2···C3vi3.491 (2)C6···H1viii3.531
N1···C4iv3.317 (2)
C1—O2—H199.8C7—C6—H4108.4
C3—N1—C6125.8 (2)C7—C6—H5108.4
C3—N1—H3117.1H4—C6—H5109.5
C6—N1—H3117.1C6—C7—C8112.3 (2)
O2—C1—C2118.6 (2)C6—C7—H6108.8
O2—C1—C5i119.7 (2)C6—C7—H7108.8
C2—C1—C5i121.7 (2)C8—C7—H6108.7
C1—C2—C3120.1 (2)C8—C7—H7108.8
C1—C2—H2120.0H6—C7—H7109.5
C3—C2—H2120.0C7—C8—C9114.9 (2)
N1—C3—C2124.4 (2)C7—C8—H8108.1
N1—C3—C4115.7 (2)C7—C8—H9108.1
C2—C3—C4119.9 (2)C9—C8—H8108.1
O1—C4—C3118.2 (2)C9—C8—H9108.1
O1—C4—C5123.3 (2)H8—C8—H9109.5
C3—C4—C5118.5 (2)C8—C9—H10109.5
C1i—C5—C4120.2 (2)C8—C9—H11109.5
C1i—C5—C5i118.5 (2)C8—C9—H12109.5
C4—C5—C5i121.3 (2)H10—C9—H11109.4
N1—C6—C7113.6 (2)H10—C9—H12109.4
N1—C6—H4108.4H11—C9—H12109.5
N1—C6—H5108.4
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+2, z+2; (iii) x1, y, z; (iv) x+1, y+2, z+2; (v) x, y+1, z+2; (vi) x+1, y, z; (vii) x1, y+1, z; (viii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1i1.061.492.517 (2)161
N1—H3···O10.952.242.664 (2)106
N1—H3···O1ii0.952.042.871 (2)146
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+2, z+2.
 

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