4,8-Bis­[(4-butyl­phenyl)­amino]-1,5-naphthalene­dione

The title compound, C₃₀H₃₂N₂O₂, is an amino­naphtho­quinone derivative that exhibits a third-order non-linear optical susceptibility. The centrosymmetric amino­naphtho­quinone moieties are connected by bifurcated N—H...O hydrogen bonds to form a ribbon structure along the c axis. The mol­ecules are stacked along the a axis, with overlap occurring only at the periphery of the naphtho­quinone skeleton.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.097
• wR factor = 0.209
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.88

Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.566     0.988
            Tmin' and Tmax expected:      0.801     0.988
            RR' =      0.706
            Please check that your absorption correction is appropriate.
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           68.00
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               1885
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2163
           Completeness (_total/calc)             87.15%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.87
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.70

Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....       P -1
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ...........          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2       =       5.39 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C5_a     =       5.29 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C1_a     =       5.29 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   7 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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)

Crystal data

C30H32N2O2	Z = 1
Mr = 452.60	F(000) = 242.0
Triclinic, P1	Dx = 1.259 Mg m^−3
Hall symbol: P -1	Cu Kα radiation, λ = 1.5418 Å
a = 6.582 (5) Å	Cell parameters from 3798 reflections
b = 11.377 (5) Å	θ = 3.9–68.0°
c = 8.236 (4) Å	µ = 0.62 mm^−1
α = 85.46 (5)°	T = 296 K
β = 76.18 (4)°	Platelet, black
γ = 89.29 (5)°	0.35 × 0.06 × 0.02 mm
V = 597.0 (6) Å^3

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	1104 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.097
48 frames, delta ω = 15 deg scans	θmax = 68.0°
Absorption correction: multi-scan (Higashi, 1995)	h = −6→6
Tmin = 0.566, Tmax = 0.988	k = −13→13
4848 measured reflections	l = −9→9
1885 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.097	w = 1/[σ^2(Fo^2) + (0.045[Max(Fo^2,0) + 2Fc^2]/3)^2]
wR(F^2) = 0.209	(Δ/σ)max = 0.010
S = 1.55	Δρmax = 0.53 e Å^−3
1759 reflections	Δρmin = −0.46 e Å^−3
154 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6377 (4)	0.4845 (2)	0.8253 (3)	0.0330 (7)
N1	0.6864 (4)	0.3864 (3)	0.1729 (4)	0.0310 (9)
C1	0.6410 (6)	0.4653 (3)	0.6730 (4)	0.028 (1)
C2	0.8015 (6)	0.3892 (3)	0.5870 (4)	0.034 (1)
C3	0.8143 (6)	0.3665 (3)	0.4265 (4)	0.029 (1)
C4	0.6692 (6)	0.4144 (3)	0.3333 (4)	0.0267 (10)
C5	0.5092 (5)	0.4867 (3)	0.4142 (4)	0.0235 (10)
C6	0.8491 (6)	0.3188 (3)	0.0787 (4)	0.0266 (10)
C7	1.0558 (6)	0.3552 (3)	0.0385 (4)	0.029 (1)
C8	1.2081 (6)	0.2880 (3)	−0.0550 (4)	0.030 (1)
C9	1.1570 (6)	0.1851 (3)	−0.1176 (4)	0.0255 (10)
C10	0.9492 (6)	0.1503 (3)	−0.0770 (5)	0.030 (1)
C11	0.7943 (6)	0.2178 (3)	0.0159 (5)	0.032 (1)
C12	1.3305 (6)	0.1138 (3)	−0.2207 (5)	0.038 (1)
C13	1.3704 (6)	0.1488 (3)	−0.4110 (5)	0.032 (1)
C14	1.1937 (6)	0.1113 (3)	−0.4875 (5)	0.038 (1)
C15	1.2488 (6)	0.1405 (4)	−0.6772 (5)	0.044 (1)
H1	0.8995	0.3546	0.6442	0.0412*
H2	0.9232	0.3171	0.3730	0.0346*
H3	0.5804	0.4145	0.1193	0.0372*
H4	1.0929	0.4271	0.0757	0.0342*
H5	1.3504	0.3122	−0.0773	0.0363*
H6	0.9118	0.0783	−0.1138	0.0363*
H7	0.6515	0.1949	0.0365	0.0383*
H8	1.4558	0.1262	−0.1861	0.0454*
H9	1.2929	0.0327	−0.2008	0.0454*
H10	1.4961	0.1125	−0.4662	0.0382*
H11	1.3858	0.2321	−0.4288	0.0382*
H12	1.0695	0.1517	−0.4391	0.0450*
H13	1.1713	0.0287	−0.4644	0.0450*
H14	1.3713	0.0990	−0.7266	0.0526*
H15	1.1362	0.1177	−0.7220	0.0526*
H16	1.2732	0.2228	−0.7011	0.0526*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.027 (1)	0.050 (2)	0.025 (1)	0.007 (1)	−0.012 (1)	−0.007 (1)
N1	0.028 (2)	0.043 (2)	0.025 (2)	−0.001 (2)	−0.012 (1)	0.000 (1)
C1	0.021 (2)	0.031 (2)	0.028 (2)	0.006 (2)	−0.002 (2)	−0.002 (2)
C2	0.030 (2)	0.044 (2)	0.037 (2)	0.012 (2)	−0.024 (2)	−0.003 (2)
C3	0.028 (2)	0.033 (2)	0.028 (2)	0.005 (2)	−0.014 (2)	−0.001 (2)
C4	0.032 (2)	0.027 (2)	0.024 (2)	0.004 (2)	−0.013 (2)	0.002 (1)
C5	0.014 (2)	0.034 (2)	0.025 (2)	0.009 (2)	−0.010 (1)	−0.005 (2)
C6	0.025 (2)	0.027 (2)	0.029 (2)	0.002 (2)	−0.011 (2)	0.000 (2)
C7	0.031 (2)	0.027 (2)	0.029 (2)	0.000 (2)	−0.009 (2)	−0.003 (2)
C8	0.028 (2)	0.039 (2)	0.027 (2)	0.001 (2)	−0.014 (2)	0.000 (2)
C9	0.018 (2)	0.032 (2)	0.025 (2)	0.003 (2)	−0.005 (1)	0.001 (2)
C10	0.028 (2)	0.031 (2)	0.031 (2)	0.000 (2)	−0.008 (2)	0.002 (2)
C11	0.028 (2)	0.035 (2)	0.036 (2)	0.005 (2)	−0.016 (2)	0.000 (2)
C12	0.035 (2)	0.041 (2)	0.041 (2)	0.006 (2)	−0.016 (2)	−0.011 (2)
C13	0.025 (2)	0.036 (2)	0.033 (2)	−0.006 (2)	−0.002 (2)	−0.006 (2)
C14	0.027 (2)	0.048 (3)	0.036 (2)	0.000 (2)	−0.004 (2)	−0.009 (2)
C15	0.033 (2)	0.059 (3)	0.036 (2)	0.005 (2)	−0.002 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C1	1.286 (4)	C9—C10	1.383 (5)
N1—C4	1.362 (4)	C9—C12	1.519 (5)
N1—C6	1.421 (4)	C10—C11	1.384 (5)
N1—H3	0.950	C10—H6	0.950
C1—C2	1.444 (5)	C11—H7	0.950
C1—C5^i	1.433 (4)	C12—C13	1.546 (5)
C2—C3	1.350 (5)	C12—H8	0.950
C2—H1	0.950	C12—H9	0.950
C3—C4	1.438 (4)	C13—C14	1.529 (5)
C3—H2	0.950	C13—H10	0.950
C4—C5	1.401 (4)	C13—H11	0.950
C5—C5^i	1.445 (6)	C14—C15	1.527 (5)
C6—C7	1.381 (5)	C14—H12	0.950
C6—C11	1.383 (5)	C14—H13	0.950
C7—C8	1.374 (5)	C15—H14	0.950
C7—H4	0.950	C15—H15	0.950
C8—C9	1.392 (5)	C15—H16	0.950
C8—H5	0.950
O1···O1^ii	3.056 (5)	O1···C11^iii	3.561 (4)
O1···N1^iii	3.077 (4)	N1···C7^vi	3.529 (4)
O1···C7^iv	3.186 (4)	C7···C7^vi	3.411 (7)
O1···C6^iii	3.247 (4)	C8···C15^iii	3.483 (6)
O1···C8^v	3.527 (5)
C4—N1—C6	125.6 (3)	C9—C10—C11	121.6 (3)
C4—N1—H3	117.2	C9—C10—H6	119.2
C6—N1—H3	117.2	C11—C10—H6	119.2
O1—C1—C2	118.1 (3)	C6—C11—C10	119.4 (4)
O1—C1—C5^i	123.4 (3)	C6—C11—H7	120.3
C2—C1—C5^i	118.5 (3)	C10—C11—H7	120.3
C1—C2—C3	120.9 (3)	C9—C12—C13	112.7 (3)
C1—C2—H1	119.6	C9—C12—H8	108.7
C3—C2—H1	119.5	C9—C12—H9	108.7
C2—C3—C4	122.5 (3)	C13—C12—H8	108.7
C2—C3—H2	118.8	C13—C12—H9	108.7
C4—C3—H2	118.7	H8—C12—H9	109.5
N1—C4—C3	120.0 (3)	C12—C13—C14	113.3 (3)
N1—C4—C5	121.9 (3)	C12—C13—H10	108.5
C3—C4—C5	118.0 (3)	C12—C13—H11	108.5
C1^i—C5—C4	119.9 (3)	C14—C13—H10	108.5
C1^i—C5—C5^i	119.0 (4)	C14—C13—H11	108.5
C4—C5—C5^i	121.1 (4)	H10—C13—H11	109.5
N1—C6—C7	122.2 (3)	C13—C14—C15	110.8 (3)
N1—C6—C11	118.0 (3)	C13—C14—H12	109.1
C7—C6—C11	119.6 (4)	C13—C14—H13	109.1
C6—C7—C8	120.4 (3)	C15—C14—H12	109.1
C6—C7—H4	119.8	C15—C14—H13	109.1
C8—C7—H4	119.8	H12—C14—H13	109.5
C7—C8—C9	121.0 (4)	C14—C15—H14	109.5
C7—C8—H5	119.5	C14—C15—H15	109.5
C9—C8—H5	119.5	C14—C15—H16	109.5
C8—C9—C10	117.9 (3)	H14—C15—H15	109.5
C8—C9—C12	119.1 (3)	H14—C15—H16	109.5
C10—C9—C12	123.0 (3)	H15—C15—H16	109.5

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z+1; (vi) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···O1^i	0.95	1.82	2.572 (4)	134
N1—H3···O1^vii	0.95	2.43	3.077 (4)	125

Symmetry codes: (i) −x+1, −y+1, −z+1; (vii) x, y, z−1.