5,7,12,14-Tetra­hydro­[2,3-b]quinolinoacridine (β form)

The title compound, C₂₀H₁₂N₂O₂, is a centrosymmetric pigment mol­ecule. The mol­ecules are doubly linked via N—H...O hydrogen bonds, forming ribbons along [110] and [10].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.160
• wR factor = 0.431
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFMX01_ALERT_2_A  The maximum difference density is > 0.1*ZMAX*2.00
            _refine_diff_density_max given =      2.400
            Test value =      1.600
PLAT097_ALERT_2_A Maximum (Positive) Residual Density ............       2.40 e/A   

Alert level B
RFACG01_ALERT_3_B  The value of the R factor is > 0.15
            R factor given   0.160
RFACR01_ALERT_3_B  The value of the weighted R factor is > 0.35
            Weighted R factor given   0.431
PLAT082_ALERT_2_B High R1 Value ..................................       0.16
PLAT084_ALERT_2_B High R2 Value ..................................       0.43
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       5.00

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.120
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C8      ..       6.34 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

5,7,12,14-Tetrahydro[2,3-b]quinolinoacridine (β form)

Crystal data

C20H12N2O2	F(000) = 324.00
Mr = 312.32	Dx = 1.566 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 4867 reflections
a = 5.7366 (6) Å	θ = 3.0–68.3°
b = 3.8851 (4) Å	µ = 0.83 mm^−1
c = 29.880 (4) Å	T = 296 K
β = 95.861 (8)°	Platelet, red
V = 662.46 (13) Å^3	0.42 × 0.20 × 0.04 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	977 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.120
ω scans	θmax = 68.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.705, Tmax = 0.965	k = −4→4
5102 measured reflections	l = −35→35
1187 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.160	w = 1/[σ^2(Fo^2) + (0.1985P)^2 + 9.1P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.431	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 2.40 e Å^−3
1187 reflections	Δρmin = −0.48 e Å^−3
110 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2 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	−0.2937 (11)	0.5833 (17)	0.0891 (2)	0.0443 (18)
N1	0.3029 (10)	1.1530 (15)	0.07695 (19)	0.0234 (15)
C1	−0.0030 (11)	0.7669 (18)	0.1684 (2)	0.0207 (15)
C2	0.1495 (12)	0.8383 (18)	0.2046 (2)	0.0234 (17)
C3	0.3608 (12)	1.0140 (18)	0.1990 (2)	0.0233 (16)
C4	0.4094 (12)	1.1109 (18)	0.1571 (2)	0.0213 (16)
C5	0.2531 (11)	1.0417 (17)	0.1193 (2)	0.0204 (16)
C6	0.1526 (11)	1.0778 (18)	0.0388 (2)	0.0213 (16)
C7	−0.0550 (11)	0.8919 (17)	0.0422 (2)	0.0190 (16)
C8	−0.1149 (11)	0.7700 (18)	0.0858 (2)	0.0181 (15)
C9	0.0444 (11)	0.8615 (17)	0.1246 (2)	0.0200 (16)
C10	0.2085 (12)	1.1838 (18)	−0.0036 (2)	0.0202 (15)
H1N	0.4283	1.2697	0.0744	0.028*
H1	−0.1421	0.6532	0.1724	0.025*
H2	0.1160	0.7724	0.2332	0.028*
H3	0.4664	1.0632	0.2239	0.028*
H4	0.5490	1.2249	0.1537	0.026*
H10	0.3467	1.3040	−0.0062	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.043 (3)	0.045 (3)	0.045 (3)	−0.003 (3)	0.002 (2)	−0.002 (2)
N1	0.018 (3)	0.018 (3)	0.035 (3)	0.000 (2)	0.005 (2)	−0.000 (2)
C1	0.009 (3)	0.020 (3)	0.032 (3)	0.003 (2)	0.002 (2)	−0.002 (2)
C2	0.024 (4)	0.022 (3)	0.026 (3)	0.006 (3)	0.007 (2)	0.002 (2)
C3	0.019 (3)	0.023 (3)	0.026 (3)	0.002 (3)	−0.003 (2)	−0.001 (2)
C4	0.011 (3)	0.018 (3)	0.034 (3)	−0.002 (2)	0.001 (2)	−0.002 (2)
C5	0.018 (3)	0.014 (3)	0.029 (3)	0.006 (2)	0.004 (2)	0.000 (2)
C6	0.016 (3)	0.017 (3)	0.031 (3)	0.007 (2)	−0.000 (2)	−0.002 (2)
C7	0.015 (3)	0.016 (3)	0.027 (3)	0.008 (2)	0.004 (2)	−0.001 (2)
C8	0.008 (3)	0.019 (3)	0.027 (3)	0.004 (2)	0.003 (2)	0.000 (2)
C9	0.014 (3)	0.014 (3)	0.031 (3)	0.001 (2)	0.001 (2)	0.002 (2)
C10	0.013 (3)	0.017 (3)	0.031 (3)	0.002 (2)	0.005 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C8	1.269 (9)	C3—H3	0.930
N1—C5	1.394 (8)	C4—C5	1.395 (9)
N1—C6	1.390 (8)	C4—H4	0.930
N1—H1N	0.860	C5—C9	1.409 (9)
C1—C2	1.348 (9)	C6—C7	1.406 (9)
C1—C9	1.415 (9)	C6—C10	1.398 (9)
C1—H1	0.930	C7—C8	1.459 (9)
C2—C3	1.416 (10)	C7—C10^i	1.410 (9)
C2—H2	0.930	C8—C9	1.444 (9)
C3—C4	1.363 (10)	C10—H10	0.930
O1···H1N^ii	2.019	H3···H3^v	2.497
H1N···O1^iii	2.019	H4···H1^iii	2.454
H1···H4^ii	2.454	H10···H10^vi	2.328
H3···H3^iv	2.497
C5—N1—C6	120.8 (5)	C4—C5—C9	119.3 (6)
C5—N1—H1N	119.6	N1—C6—C7	120.4 (6)
C6—N1—H1N	119.6	N1—C6—C10	120.0 (6)
C2—C1—C9	121.3 (6)	C7—C6—C10	119.5 (6)
C2—C1—H1	119.3	C6—C7—C8	120.7 (5)
C9—C1—H1	119.4	C6—C7—C10^i	120.6 (6)
C1—C2—C3	119.8 (6)	C8—C7—C10^i	118.6 (6)
C1—C2—H2	120.1	O1—C8—C7	121.4 (5)
C3—C2—H2	120.1	O1—C8—C9	121.9 (6)
C2—C3—C4	120.0 (6)	C7—C8—C9	116.6 (5)
C2—C3—H3	120.0	C1—C9—C5	118.6 (5)
C4—C3—H3	120.0	C1—C9—C8	120.9 (6)
C3—C4—C5	121.0 (6)	C5—C9—C8	120.5 (6)
C3—C4—H4	119.5	C6—C10—C7^i	119.8 (6)
C5—C4—H4	119.5	C6—C10—H10	120.1
N1—C5—C4	120.0 (6)	C7^i—C10—H10	120.1
N1—C5—C9	120.7 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^iii	0.86	2.02	2.848 (8)	161

Symmetry code: (iii) x+1, y+1, z.