Crystal structure of 9,9′-{(1E,1′E)-[1,4-phenyl­enebis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(2,3,6,7-tetra­hydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol)

The whole mol­ecule of the title compound is generated by inversion symmetry; the central benzene ring being situated about a crystallographic inversion center. The aromatic ring of the julolidine moiety is inclined to the central benzene ring by 33.70 (12)°, and the conformation about the C=N bonds is E. There are two intra­molecular O—H...N hydrogen bonds in the mol­ecule, generating S(6) ring motifs.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.127
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C4      ..        6.3 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.681 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          39 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

9,9'-{(1E,1'E)-[1,4-Phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol)

Crystal data

C32H34N4O2	F(000) = 540
Mr = 506.63	Dx = 1.331 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3371 reflections
a = 5.1776 (3) Å	θ = 2.4–26.5°
b = 27.9346 (17) Å	µ = 0.08 mm^−1
c = 8.7893 (6) Å	T = 100 K
β = 96.203 (2)°	Block, yellow
V = 1263.79 (14) Å^3	0.20 × 0.15 × 0.12 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer	2243 independent reflections
Radiation source: fine-focus sealed tube	1469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
/w–scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −6→6
Tmin = 0.783, Tmax = 0.990	k = −33→33
15125 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0483P)^2 + 0.7868P] where P = (Fo^2 + 2Fc^2)/3
2243 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5852 (3)	0.64668 (6)	0.15270 (19)	0.0327 (5)
H1A	0.4785	0.6259	0.1246	0.049*
N2	1.2746 (4)	0.67853 (7)	0.5427 (2)	0.0250 (5)
N1	0.3470 (4)	0.56564 (7)	0.1548 (2)	0.0259 (5)
C3	0.1732 (4)	0.53146 (8)	0.0816 (3)	0.0216 (6)
C11	1.0954 (4)	0.64728 (8)	0.4704 (3)	0.0208 (6)
C7	1.0677 (4)	0.60049 (8)	0.5312 (3)	0.0212 (6)
C1	−0.2269 (4)	0.51736 (9)	−0.0764 (3)	0.0249 (6)
H1	−0.3807	0.5292	−0.1271	0.030*
C15	0.9341 (4)	0.66163 (8)	0.3388 (3)	0.0229 (6)
C16	0.7394 (5)	0.63101 (9)	0.2775 (3)	0.0250 (6)
C6	0.8730 (4)	0.57163 (9)	0.4650 (3)	0.0245 (6)
H6	0.8546	0.5412	0.5055	0.029*
C2	−0.0546 (4)	0.54825 (9)	0.0030 (3)	0.0240 (6)
H2	−0.0918	0.5808	0.0039	0.029*
C5	0.7015 (5)	0.58567 (8)	0.3400 (3)	0.0241 (6)
C4	0.5029 (5)	0.55395 (9)	0.2728 (3)	0.0277 (6)
H4	0.4865	0.5239	0.3161	0.033*
C8	1.2531 (5)	0.58325 (9)	0.6635 (3)	0.0277 (6)
H8A	1.3963	0.5663	0.6250	0.033*
H8B	1.1643	0.5611	0.7251	0.033*
C12	1.3361 (5)	0.72291 (9)	0.4669 (3)	0.0305 (6)
H12A	1.4648	0.7165	0.3971	0.037*
H12B	1.4101	0.7456	0.5429	0.037*
C10	1.4682 (5)	0.66195 (9)	0.6634 (3)	0.0305 (6)
H10A	1.5310	0.6889	0.7264	0.037*
H10B	1.6144	0.6484	0.6181	0.037*
C14	0.9740 (5)	0.70887 (9)	0.2652 (3)	0.0307 (6)
H14A	0.8078	0.7212	0.2203	0.037*
H14B	1.0841	0.7046	0.1837	0.037*
C13	1.0976 (5)	0.74444 (9)	0.3793 (3)	0.0313 (6)
H13A	1.1453	0.7730	0.3264	0.038*
H13B	0.9744	0.7535	0.4499	0.038*
C9	1.3577 (5)	0.62498 (9)	0.7617 (3)	0.0309 (6)
H9A	1.2190	0.6390	0.8130	0.037*
H9B	1.4917	0.6138	0.8393	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0348 (11)	0.0320 (11)	0.0288 (10)	−0.0051 (8)	−0.0072 (9)	0.0013 (8)
N2	0.0219 (11)	0.0267 (12)	0.0257 (12)	−0.0030 (10)	−0.0006 (9)	−0.0002 (9)
N1	0.0213 (11)	0.0324 (13)	0.0233 (11)	−0.0016 (10)	−0.0003 (10)	−0.0044 (10)
C3	0.0198 (12)	0.0261 (13)	0.0198 (13)	−0.0057 (11)	0.0060 (11)	−0.0059 (11)
C11	0.0174 (12)	0.0239 (14)	0.0219 (13)	−0.0019 (10)	0.0057 (11)	−0.0050 (10)
C7	0.0213 (13)	0.0239 (14)	0.0192 (13)	0.0009 (11)	0.0061 (11)	−0.0041 (11)
C1	0.0187 (13)	0.0316 (15)	0.0241 (14)	0.0004 (11)	0.0016 (11)	−0.0006 (11)
C15	0.0248 (13)	0.0244 (13)	0.0202 (13)	−0.0008 (11)	0.0049 (11)	0.0019 (11)
C16	0.0229 (13)	0.0350 (15)	0.0165 (12)	0.0061 (12)	−0.0010 (11)	−0.0004 (11)
C6	0.0273 (14)	0.0252 (14)	0.0217 (13)	0.0020 (11)	0.0065 (11)	−0.0004 (11)
C2	0.0239 (13)	0.0233 (14)	0.0251 (14)	−0.0017 (11)	0.0042 (11)	−0.0038 (11)
C5	0.0263 (14)	0.0236 (14)	0.0234 (14)	−0.0039 (11)	0.0070 (12)	−0.0052 (11)
C4	0.0312 (14)	0.0263 (14)	0.0270 (14)	0.0006 (12)	0.0098 (12)	−0.0024 (12)
C8	0.0297 (15)	0.0305 (15)	0.0229 (14)	0.0056 (12)	0.0030 (12)	0.0031 (11)
C12	0.0275 (14)	0.0250 (14)	0.0394 (16)	−0.0064 (12)	0.0048 (12)	−0.0054 (12)
C10	0.0253 (13)	0.0350 (15)	0.0296 (15)	0.0023 (12)	−0.0043 (12)	−0.0082 (12)
C14	0.0289 (14)	0.0323 (15)	0.0305 (15)	−0.0034 (12)	0.0015 (12)	0.0033 (12)
C13	0.0356 (15)	0.0255 (14)	0.0329 (15)	−0.0034 (12)	0.0047 (13)	0.0045 (12)
C9	0.0292 (14)	0.0384 (16)	0.0233 (14)	0.0096 (13)	−0.0056 (11)	−0.0031 (12)

Geometric parameters (Å, º)

O1—C16	1.358 (3)	C6—H6	0.9300
O1—H1A	0.8200	C2—H2	0.9300
N2—C11	1.378 (3)	C5—C4	1.435 (3)
N2—C10	1.454 (3)	C4—H4	0.9300
N2—C12	1.459 (3)	C8—C9	1.515 (3)
N1—C4	1.285 (3)	C8—H8A	0.9700
N1—C3	1.418 (3)	C8—H8B	0.9700
C3—C2	1.383 (3)	C12—C13	1.508 (3)
C3—C1^i	1.394 (3)	C12—H12A	0.9700
C11—C15	1.410 (3)	C12—H12B	0.9700
C11—C7	1.425 (3)	C10—C9	1.499 (4)
C7—C6	1.370 (3)	C10—H10A	0.9700
C7—C8	1.505 (3)	C10—H10B	0.9700
C1—C2	1.376 (3)	C14—C13	1.505 (3)
C1—C3^i	1.394 (3)	C14—H14A	0.9700
C1—H1	0.9300	C14—H14B	0.9700
C15—C16	1.386 (3)	C13—H13A	0.9700
C15—C14	1.494 (3)	C13—H13B	0.9700
C16—C5	1.403 (3)	C9—H9A	0.9700
C6—C5	1.392 (3)	C9—H9B	0.9700
C16—O1—H1A	109.5	C7—C8—H8A	109.5
C11—N2—C10	120.75 (19)	C9—C8—H8A	109.5
C11—N2—C12	119.8 (2)	C7—C8—H8B	109.5
C10—N2—C12	115.88 (19)	C9—C8—H8B	109.5
C4—N1—C3	120.5 (2)	H8A—C8—H8B	108.1
C2—C3—C1^i	118.6 (2)	N2—C12—C13	111.4 (2)
C2—C3—N1	117.6 (2)	N2—C12—H12A	109.3
C1^i—C3—N1	123.7 (2)	C13—C12—H12A	109.3
N2—C11—C15	120.5 (2)	N2—C12—H12B	109.3
N2—C11—C7	119.9 (2)	C13—C12—H12B	109.3
C15—C11—C7	119.6 (2)	H12A—C12—H12B	108.0
C6—C7—C11	118.7 (2)	N2—C10—C9	111.4 (2)
C6—C7—C8	121.2 (2)	N2—C10—H10A	109.4
C11—C7—C8	120.1 (2)	C9—C10—H10A	109.4
C2—C1—C3^i	120.6 (2)	N2—C10—H10B	109.4
C2—C1—H1	119.7	C9—C10—H10B	109.4
C3^i—C1—H1	119.7	H10A—C10—H10B	108.0
C16—C15—C11	119.0 (2)	C15—C14—C13	111.3 (2)
C16—C15—C14	120.4 (2)	C15—C14—H14A	109.4
C11—C15—C14	120.6 (2)	C13—C14—H14A	109.4
O1—C16—C15	117.0 (2)	C15—C14—H14B	109.4
O1—C16—C5	120.8 (2)	C13—C14—H14B	109.4
C15—C16—C5	122.1 (2)	H14A—C14—H14B	108.0
C7—C6—C5	123.1 (2)	C12—C13—C14	110.0 (2)
C7—C6—H6	118.4	C12—C13—H13A	109.7
C5—C6—H6	118.4	C14—C13—H13A	109.7
C1—C2—C3	120.8 (2)	C12—C13—H13B	109.7
C1—C2—H2	119.6	C14—C13—H13B	109.7
C3—C2—H2	119.6	H13A—C13—H13B	108.2
C6—C5—C16	117.3 (2)	C10—C9—C8	109.7 (2)
C6—C5—C4	121.2 (2)	C10—C9—H9A	109.7
C16—C5—C4	121.4 (2)	C8—C9—H9A	109.7
N1—C4—C5	122.3 (2)	C10—C9—H9B	109.7
N1—C4—H4	118.8	C8—C9—H9B	109.7
C5—C4—H4	118.8	H9A—C9—H9B	108.2
C7—C8—C9	110.7 (2)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C5–C7/C11/C15/C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.85	2.579 (3)	148
C10—H10B···Cg^ii	0.97	2.68	3.603 (3)	160

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