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The title compound, C20H16N2O, has two mol­ecules in the asymmetric unit and the crystal structure shows that the central pyridine ring of each mol­ecule has a flat boat conformation. The terminal C atom in one of the mol­ecules is disordered over two positions, with relative occupancies of 0.594 (14) and 0.398 (14). Intermolecular C—H...N and C—H...π interactions and π–π stacking, along with intramolecular C—H...N and C—H...π interactions, help to stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102018383/de1195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102018383/de1195Isup2.hkl
Contains datablock I

CCDC reference: 201271

Comment top

The title compound, (I), belongs to the 2-pyridine class of compounds, which have a wide spectrum of biological activities (Perez-Medina et al., 1947; Lesher & Grvet, 1973). The present work continues our structural studies of the 2-pyridine group of compounds (Patel et al., 2002a,b). \sch

Compound (I) crystallizes in the monoclinic space group P21/c with two molecules in the asymmetric unit, denoted A and B. A perspective view of the two molecules is shown in Fig. 1. The pyridine rings of molecules A and B have quite similar geometries. The shortening of the C—N distances [1.313 (3) and 1.346 (3) Å in molecule A, and 1.349 (3) and 1.299 (3) Å in molecule B] and the opening of the N1—C1—C2 angle [123.9 (2)° in molecule A and 124.6 (3)° in molecule B] may be attributed to the size of the substituent at C1, correlating well with the values observed in the ortho-substituted isopropylidine dioxy-propyloxy derivative (Patel et al., 2002c). However, when the ortho substituent is only an O atom, the bond length and angle are normal (Patel et al., 2002a,b). The bond distances and angles of the phenyl rings of molecules A and B in (I) are consistent with those observed in other similar structures (Patel et al., 2002b; Black et al., 1992; Hussain et al., 1996).

The flat boat conformation of the dihydropyridine ring of molecules A and B is reported in the literature for compounds incorporating this moiety (Lokaj et al., 1991; Fonseca et al., 1986). The cyano atoms C18 and N2 of molecule A deviate by 0.173 (4) and 0.310 (5) Å, respectively, from the pyridine ring plane, while for molecule B, atoms C18' [-0.031 (4) Å] and N2' [-0.058 (6) Å] are coplanar to it. The phenyl rings of both molecules are planar. Steric hindrances rotate the phenyl rings out of the plane of the central pyridine ring by 35.49 (8) and 24.61 (1)° (molecule A), and 41.0 (1) and 22.3 (1)° (molecule B). A similar orientation of the phenyl rings has been observed in other derivatives of 1,4-dihydropyridine reported by our group and by others (Patel et al., 2002a; Bolte, 1998).

The significant difference in the conformations of molecules A and B is in the relative orientations of the ethoxy moiety. The ethoxy group in molecule B is orthogonal to the pyridine ring plane [C1'-O1'-C19'-C20' 94.1 (6)°], thereby avoiding steric interaction, while in molecule A it is coplanar with the heterocyclic ring plane [C1—O1—C19—C20 170.1 (2)°].

The terminal ethoxy C atom of molecule B is disordered over two positions, resulting in a shortening of the C19'-C20' [1.350 (6) Å] and C19'-C20A [1.392 (9) Å] distances. The torsion angles defining the orientations of various substituents at the central pyridine ring are summarized as follows for molecule A, with the values for molecule B given in brackets: C3—C2—C18—N2 146 (6)° [35 (43)°], C1—C2—C18—N2 - 33 (6)° [-149 (43)], C2—C1—O1—C19 - 172.0 (2)° [179.1 (3)°] and N1—C1—O1—C19 8.1 (3)° [-0.6 (4)°]

An intermolecular network of C—H···π and π-π stacking interactions plays a significant role in the stability of the structure of (I). In addition, there is an intramolecular C—H···N interaction (Fig. 2) involving the pyridine atom N1' and the ethoxy atom C19', with C19'···N1' 2.709 (5) Å, H19D···N1' 2.34 Å and C19'-H19D···N1' 101.9°. The cyano atom N2 of molecule A interacts with the phenyl atom C15' of a symmetry-related molecule B at (x, 3/2 - y, z - 1/2), with C15'···N2 3.399 (6) Å, H15'···N2 2.55 Å and C15'-H15'···N2 152.5°. The hydrogen bonding in the structure of (I) is supported by π-π stacking observed between the pyridine ring plane of molecule A and that of molecule B at (1 + x, y, z), with their centroids separated by 3.926 (2) Å.

There are two intramolecular C—H···π interactions in the structure of (I). In the first, a phenyl atom C13' of molecule B interacts with the pyridine ring of molecule A, with C13'···Cg1 3.392 (3) Å, H13'···Cg1 3.182 Å and C13'-H13'···Cg1 95.04° (Cg1 is the centroid of the C1—C5/N1 ring). In the second interaction, the ethoxy atom C19 of molecule A interacts with the pyridine ring of molecule B, with C19···Cg2 3.868 (3) Å, H19B···Cg2 3.368 Å and C19—H19B···Cg2 114.2° (Cg2 is the centroid of the C1'-C5'/N1' ring).

There are also two intermolecular C—H···π interactions (Desiraju & Steiner, 1999) linking symmetry-related molecules A and B, and these are dominant in the structure of (I), providing strong packing. In the first of these, the phenyl atom C10 of molecule A interacts with the symmetry-related phenyl ring of molecule B at (1 + x, 3/2 - y, 1/2 + z), such that C10···Cg3 3.498 (4) Å, H10···Cg3 2.714 Å and C10—H10···Cg3 142.53° [Cg3 is the centroid of the C1'-C5'/N1' ring at (1 + x, 3/2 - y, 1/2 + z)]. In the second interaction, the ortho-substituted phenyl atom C17' of molecule B interacts with the symmetry-related phenyl ring of molecule A at (x - 1, y, z), such that C17'···Cg4 3.653 (4) Å, H17'···Cg4 2.949 Å and C17'-H17'···Cg4 133.66° [Cg4 is the centroid of the C1—C5/N1 ring at (x - 1, y, z)]. Please check that all four centroids have been defined correctly.

Experimental top

The title compound was synthesized according to the method of Shah (2000); full details of the synthesis will be published elsewhere. Thin plate-like crystals of (I) were grown by slow evaporation from a solution in a mixture of chloroform and ethanol (Ratio?).

Refinement top

H atoms were treated as riding, with C—H distances in the range 0.93–0.97 Å. Is this added text OK?

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: Please provide missing details; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965) and PLATON (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules in (I), showing the atom-numbering scheme; molecule B is labelled with primes. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the molecular packing in (I) along the bc plane, showing the hydrogen-bonding interactions.
3-cyano-2-ethoxy-4,6-diphenylpyridine top
Crystal data top
C20H16N2OF(000) = 1264
Mr = 300.31Dx = 1.214 Mg m3
Dm = 1.204 Mg m3
Dm measured by flotation in aqueous potassium iodide
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.5542 (10) Åθ = 25–35°
b = 32.027 (3) ŵ = 0.60 mm1
c = 12.3910 (7) ÅT = 293 K
β = 104.493 (3)°Plate-like, colourless
V = 3286.6 (5) Å30.2 × 0.1 × 0.1 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
3150 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 67.9°, θmin = 2.8°
ω/2θ scansh = 1010
Absorption correction: empirical (using intensity measurements)
ψ scan
k = 030
Tmin = 0.930, Tmax = 0.940l = 014
6001 measured reflections2 standard reflections every 60 min
6001 independent reflections intensity decay: 1%
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.077P)2 + 0.3042P]
wR(F2) = 0.160(Δ/σ)max = 0.050
S = 1.02Δρmax = 0.13 e Å3
5612 reflectionsΔρmin = 0.21 e Å3
426 parameters
Crystal data top
C20H16N2OV = 3286.6 (5) Å3
Mr = 300.31Z = 4
Monoclinic, P21/cCu Kα radiation
a = 8.5542 (10) ŵ = 0.60 mm1
b = 32.027 (3) ÅT = 293 K
c = 12.3910 (7) Å0.2 × 0.1 × 0.1 mm
β = 104.493 (3)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3150 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
ψ scan
Rint = 0.061
Tmin = 0.930, Tmax = 0.9402 standard reflections every 60 min
6001 measured reflections intensity decay: 1%
6001 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511 restraint
wR(F2) = 0.160H-atom parameters constrained
S = 1.02Δρmax = 0.13 e Å3
5612 reflectionsΔρmin = 0.21 e Å3
426 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1939 (2)0.58563 (6)0.34456 (13)0.0772 (5)
N10.2538 (2)0.59936 (6)0.17773 (15)0.0658 (5)
N20.2615 (3)0.66820 (9)0.5166 (2)0.1020 (8)
C50.3201 (3)0.62526 (8)0.11599 (19)0.0635 (6)
C40.3949 (3)0.66211 (8)0.15891 (19)0.0654 (6)
H40.44740.67810.11610.078*
C30.3926 (3)0.67551 (7)0.26572 (18)0.0618 (6)
C20.3139 (3)0.64966 (8)0.32625 (18)0.0620 (6)
C10.2537 (3)0.61100 (8)0.2793 (2)0.0671 (6)
C120.3048 (3)0.61208 (8)0.0013 (2)0.0699 (7)
C130.2829 (4)0.56997 (10)0.0280 (3)0.1040 (11)
H130.28090.55050.02740.125*
C140.2640 (5)0.55688 (12)0.1376 (3)0.1271 (14)
H140.24830.52870.15520.152*
C150.2683 (4)0.58474 (12)0.2184 (3)0.1067 (11)
H150.25670.57560.29130.128*
C160.2894 (4)0.62594 (11)0.1939 (2)0.0955 (9)
H160.29130.64500.25020.115*
C170.3082 (3)0.63993 (9)0.0849 (2)0.0845 (8)
H170.32310.66820.06870.101*
C60.4711 (3)0.71525 (8)0.3104 (2)0.0661 (6)
C70.4688 (3)0.74935 (9)0.2401 (2)0.0777 (7)
H70.41650.74710.16490.093*
C80.5428 (4)0.78623 (9)0.2804 (3)0.0977 (9)
H80.53780.80890.23270.117*
C90.6245 (4)0.78994 (11)0.3910 (3)0.1037 (11)
H90.67560.81480.41800.124*
C100.6294 (4)0.75651 (11)0.4607 (3)0.0951 (9)
H100.68420.75890.53540.114*
C110.5539 (3)0.71906 (9)0.4220 (2)0.0767 (7)
H110.55870.69660.47040.092*
C180.2879 (3)0.66047 (8)0.4330 (2)0.0733 (7)
C190.1502 (4)0.54315 (9)0.3048 (2)0.0907 (9)
H19A0.23840.53030.28080.109*
H19B0.05580.54370.24220.109*
C200.1154 (4)0.51930 (11)0.3981 (3)0.1182 (12)
H20A0.08660.49120.37450.177*
H20B0.02750.53220.42090.177*
H20C0.20950.51900.45960.177*
O1'0.2988 (3)0.56023 (7)0.10045 (15)0.1171 (8)
N1'0.1940 (3)0.62550 (8)0.15259 (17)0.0803 (6)
N2'0.4032 (5)0.50945 (9)0.3087 (3)0.1307 (12)
C5'0.1502 (3)0.65433 (8)0.2340 (2)0.0691 (7)
C4'0.1670 (3)0.64747 (8)0.34133 (18)0.0637 (6)
H4'0.13160.66750.39630.076*
C3'0.2364 (3)0.61067 (8)0.36673 (19)0.0665 (6)
C2'0.2828 (3)0.58145 (8)0.2830 (2)0.0712 (7)
C1'0.2553 (4)0.59074 (9)0.1773 (2)0.0800 (8)
C12'0.0802 (3)0.69343 (10)0.2029 (2)0.0812 (8)
C13'0.0138 (3)0.69466 (11)0.1115 (2)0.0964 (10)
H13'0.01190.67070.06950.116*
C14'0.0503 (4)0.73208 (16)0.0823 (3)0.1172 (14)
H14'0.09450.73290.02100.141*
C15'0.0482 (5)0.76665 (17)0.1427 (4)0.1304 (16)
H15'0.09360.79110.12400.156*
C16'0.0205 (4)0.76648 (12)0.2323 (3)0.1214 (12)
H16'0.02390.79090.27240.146*
C17'0.0844 (4)0.72980 (11)0.2620 (3)0.0981 (10)
H17'0.13060.72960.32240.118*
C6'0.2578 (3)0.60465 (8)0.48118 (19)0.0658 (6)
C7'0.1416 (4)0.61815 (10)0.5716 (2)0.0905 (9)
H7'0.04600.62940.56140.109*
C8'0.1649 (5)0.61528 (12)0.6782 (2)0.1117 (11)
H8'0.08470.62430.73910.134*
C9'0.3065 (5)0.59906 (13)0.6938 (3)0.1171 (12)
H9'0.32370.59790.76500.141*
C10'0.4208 (4)0.58478 (11)0.6053 (3)0.0985 (10)
H10'0.51510.57310.61640.118*
C11'0.3993 (3)0.58738 (8)0.4978 (2)0.0761 (7)
H11'0.47900.57760.43750.091*
C18'0.3499 (4)0.54104 (10)0.2971 (2)0.0876 (9)
C19'0.2779 (7)0.56690 (14)0.0093 (2)0.1470 (18)
H19C0.36480.55340.06350.176*
H19D0.28210.59660.02540.176*
C20'0.1362 (8)0.5514 (3)0.0174 (6)0.115 (4)0.594 (14)
H20D0.12390.55600.09140.172*
H20E0.13270.52200.00200.172*
H20F0.05020.56520.03550.172*
C20A0.253 (2)0.5315 (3)0.0682 (6)0.121 (6)0.398 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0847 (12)0.0807 (13)0.0688 (10)0.0031 (10)0.0239 (9)0.0025 (9)
N10.0680 (13)0.0641 (13)0.0681 (12)0.0051 (10)0.0221 (10)0.0025 (9)
N20.115 (2)0.118 (2)0.0816 (16)0.0118 (16)0.0404 (15)0.0156 (14)
C50.0625 (14)0.0642 (16)0.0679 (14)0.0065 (12)0.0237 (11)0.0053 (12)
C40.0667 (15)0.0604 (16)0.0711 (14)0.0038 (12)0.0210 (11)0.0058 (11)
C30.0497 (13)0.0680 (16)0.0620 (13)0.0127 (11)0.0030 (10)0.0019 (11)
C20.0558 (13)0.0683 (16)0.0593 (13)0.0091 (12)0.0099 (11)0.0039 (11)
C10.0643 (15)0.0694 (17)0.0700 (15)0.0082 (12)0.0214 (12)0.0057 (13)
C120.0717 (16)0.0690 (18)0.0735 (15)0.0069 (13)0.0267 (12)0.0062 (12)
C130.156 (3)0.070 (2)0.102 (2)0.0176 (19)0.064 (2)0.0220 (16)
C140.192 (4)0.100 (3)0.111 (3)0.025 (3)0.077 (3)0.037 (2)
C150.127 (3)0.117 (3)0.087 (2)0.030 (2)0.0483 (19)0.034 (2)
C160.107 (2)0.114 (3)0.0711 (17)0.018 (2)0.0315 (16)0.0064 (16)
C170.095 (2)0.087 (2)0.0734 (17)0.0111 (16)0.0234 (15)0.0029 (14)
C60.0531 (13)0.0650 (16)0.0740 (15)0.0023 (11)0.0040 (11)0.0109 (12)
C70.0656 (16)0.0698 (18)0.0916 (18)0.0064 (13)0.0080 (13)0.0056 (14)
C80.090 (2)0.072 (2)0.125 (3)0.0042 (17)0.0155 (19)0.0116 (18)
C90.084 (2)0.074 (2)0.143 (3)0.0033 (16)0.011 (2)0.031 (2)
C100.0752 (19)0.098 (2)0.108 (2)0.0111 (18)0.0158 (17)0.032 (2)
C110.0618 (15)0.0769 (19)0.0846 (17)0.0012 (13)0.0057 (12)0.0107 (14)
C180.0632 (15)0.0790 (19)0.0746 (16)0.0064 (13)0.0117 (12)0.0028 (13)
C190.108 (2)0.080 (2)0.0867 (19)0.0119 (17)0.0282 (17)0.0094 (15)
C200.114 (3)0.115 (3)0.130 (3)0.014 (2)0.038 (2)0.031 (2)
O1'0.196 (2)0.0919 (15)0.0623 (11)0.0314 (15)0.0300 (13)0.0068 (10)
N1'0.0919 (17)0.0814 (17)0.0740 (14)0.0268 (13)0.0329 (12)0.0229 (12)
N2'0.205 (4)0.0679 (19)0.133 (2)0.011 (2)0.069 (2)0.0029 (16)
C5'0.0556 (14)0.0761 (18)0.0764 (16)0.0207 (12)0.0183 (12)0.0215 (14)
C4'0.0619 (14)0.0678 (16)0.0610 (13)0.0128 (12)0.0147 (11)0.0130 (11)
C3'0.0698 (15)0.0646 (16)0.0676 (14)0.0100 (12)0.0215 (12)0.0097 (12)
C2'0.0815 (18)0.0603 (16)0.0734 (16)0.0149 (13)0.0222 (13)0.0104 (13)
C1'0.107 (2)0.073 (2)0.0589 (15)0.0244 (16)0.0190 (14)0.0078 (13)
C12'0.0678 (17)0.094 (2)0.0836 (18)0.0135 (15)0.0227 (14)0.0353 (16)
C13'0.0599 (16)0.139 (3)0.095 (2)0.0294 (17)0.0270 (14)0.0531 (19)
C14'0.071 (2)0.165 (4)0.116 (3)0.011 (2)0.025 (2)0.072 (3)
C15'0.083 (2)0.159 (4)0.145 (4)0.018 (3)0.019 (2)0.072 (3)
C16'0.109 (3)0.106 (3)0.152 (3)0.015 (2)0.037 (2)0.039 (2)
C17'0.079 (2)0.097 (2)0.119 (2)0.0022 (17)0.0242 (17)0.035 (2)
C6'0.0674 (15)0.0678 (16)0.0631 (13)0.0099 (12)0.0183 (11)0.0137 (12)
C7'0.095 (2)0.102 (2)0.0706 (17)0.0126 (17)0.0140 (15)0.0032 (15)
C8'0.123 (3)0.139 (3)0.0633 (18)0.002 (2)0.0039 (18)0.0009 (17)
C9'0.131 (3)0.156 (4)0.072 (2)0.013 (3)0.041 (2)0.022 (2)
C10'0.097 (2)0.120 (3)0.091 (2)0.019 (2)0.0484 (19)0.0304 (19)
C11'0.0662 (16)0.0818 (18)0.0839 (17)0.0073 (13)0.0254 (13)0.0114 (14)
C18'0.122 (3)0.064 (2)0.0764 (17)0.0178 (18)0.0244 (17)0.0103 (14)
C19'0.237 (6)0.142 (4)0.064 (2)0.077 (3)0.040 (3)0.013 (2)
C20'0.082 (5)0.191 (8)0.075 (5)0.030 (5)0.028 (3)0.033 (5)
C20A0.190 (14)0.085 (7)0.060 (5)0.046 (7)0.019 (6)0.004 (4)
Geometric parameters (Å, º) top
O1—C11.336 (3)O1'—C19'1.431 (4)
O1—C191.463 (3)N1'—C1'1.299 (3)
N1—C11.313 (3)N1'—C5'1.349 (3)
N1—C51.346 (3)N2'—C18'1.133 (4)
N2—C181.142 (3)C5'—C4'1.391 (3)
C5—C41.384 (3)C5'—C12'1.480 (4)
C5—C121.488 (3)C4'—C3'1.391 (3)
C4—C31.396 (3)C4'—H4'0.9300
C4—H40.9300C3'—C2'1.380 (3)
C3—C21.398 (3)C3'—C6'1.487 (3)
C3—C61.480 (3)C2'—C1'1.418 (3)
C2—C11.409 (3)C2'—C18'1.444 (4)
C2—C181.437 (3)C12'—C17'1.381 (4)
C12—C171.372 (3)C12'—C13'1.390 (4)
C12—C131.390 (4)C13'—C14'1.402 (5)
C13—C141.390 (4)C13'—H13'0.9300
C13—H130.9300C14'—C15'1.339 (5)
C14—C151.349 (5)C14'—H14'0.9300
C14—H140.9300C15'—C16'1.379 (5)
C15—C161.356 (4)C15'—H15'0.9300
C15—H150.9300C16'—C17'1.384 (4)
C16—C171.393 (4)C16'—H16'0.9300
C16—H160.9300C17'—H17'0.9300
C17—H170.9300C6'—C7'1.368 (4)
C6—C111.393 (3)C6'—C11'1.392 (3)
C6—C71.394 (4)C7'—C8'1.388 (4)
C7—C81.374 (4)C7'—H7'0.9300
C7—H70.9300C8'—C9'1.376 (5)
C8—C91.379 (4)C8'—H8'0.9300
C8—H80.9300C9'—C10'1.354 (5)
C9—C101.369 (4)C9'—H9'0.9300
C9—H90.9300C10'—C11'1.391 (3)
C10—C111.389 (4)C10'—H10'0.9300
C10—H100.9300C11'—H11'0.9300
C11—H110.9300C19'—C20'1.337 (6)
C19—C201.477 (4)C19'—C20A1.394 (8)
C19—H19A0.9700C19'—H19C0.9700
C19—H19B0.9700C19'—H19D0.9700
C20—H20A0.9600C20'—H20D0.9600
C20—H20B0.9600C20'—H20E0.9600
C20—H20C0.9600C20'—H20F0.9600
O1'—C1'1.350 (3)
C1—O1—C19117.81 (19)N1'—C5'—C4'122.1 (2)
C1—N1—C5118.1 (2)N1'—C5'—C12'116.1 (2)
N1—C5—C4121.8 (2)C4'—C5'—C12'121.8 (3)
N1—C5—C12115.7 (2)C3'—C4'—C5'120.2 (2)
C4—C5—C12122.5 (2)C3'—C4'—H4'119.9
C5—C4—C3120.8 (2)C5'—C4'—H4'119.9
C5—C4—H4119.6C2'—C3'—C4'117.6 (2)
C3—C4—H4119.6C2'—C3'—C6'123.2 (2)
C4—C3—C2116.7 (2)C4'—C3'—C6'119.1 (2)
C4—C3—C6120.4 (2)C3'—C2'—C1'117.9 (2)
C2—C3—C6122.9 (2)C3'—C2'—C18'124.4 (2)
C3—C2—C1118.3 (2)C1'—C2'—C18'117.6 (2)
C3—C2—C18123.9 (2)N1'—C1'—O1'120.7 (2)
C1—C2—C18117.8 (2)N1'—C1'—C2'124.6 (3)
N1—C1—O1120.0 (2)O1'—C1'—C2'114.8 (3)
N1—C1—C2123.9 (2)C17'—C12'—C13'118.6 (3)
O1—C1—C2116.1 (2)C17'—C12'—C5'120.7 (3)
C17—C12—C13118.6 (2)C13'—C12'—C5'120.7 (3)
C17—C12—C5122.6 (2)C12'—C13'—C14'120.0 (4)
C13—C12—C5118.8 (2)C12'—C13'—H13'120.0
C14—C13—C12120.0 (3)C14'—C13'—H13'120.0
C14—C13—H13120.0C15'—C14'—C13'120.1 (4)
C12—C13—H13120.0C15'—C14'—H14'119.9
C15—C14—C13120.5 (3)C13'—C14'—H14'119.9
C15—C14—H14119.8C14'—C15'—C16'121.0 (4)
C13—C14—H14119.8C14'—C15'—H15'119.5
C14—C15—C16120.3 (3)C16'—C15'—H15'119.5
C14—C15—H15119.9C15'—C16'—C17'119.6 (4)
C16—C15—H15119.9C15'—C16'—H16'120.2
C15—C16—C17120.4 (3)C17'—C16'—H16'120.2
C15—C16—H16119.8C12'—C17'—C16'120.7 (3)
C17—C16—H16119.8C12'—C17'—H17'119.6
C12—C17—C16120.2 (3)C16'—C17'—H17'119.6
C12—C17—H17119.9C7'—C6'—C11'119.0 (2)
C16—C17—H17119.9C7'—C6'—C3'120.1 (2)
C11—C6—C7118.4 (2)C11'—C6'—C3'120.8 (2)
C11—C6—C3121.1 (2)C6'—C7'—C8'120.7 (3)
C7—C6—C3120.4 (2)C6'—C7'—H7'119.6
C8—C7—C6120.9 (3)C8'—C7'—H7'119.6
C8—C7—H7119.6C9'—C8'—C7'120.0 (3)
C6—C7—H7119.6C9'—C8'—H8'120.0
C7—C8—C9120.5 (3)C7'—C8'—H8'120.0
C7—C8—H8119.7C10'—C9'—C8'119.8 (3)
C9—C8—H8119.7C10'—C9'—H9'120.1
C10—C9—C8119.2 (3)C8'—C9'—H9'120.1
C10—C9—H9120.4C9'—C10'—C11'120.9 (3)
C8—C9—H9120.4C9'—C10'—H10'119.5
C9—C10—C11121.3 (3)C11'—C10'—H10'119.5
C9—C10—H10119.4C10'—C11'—C6'119.6 (3)
C11—C10—H10119.4C10'—C11'—H11'120.2
C10—C11—C6119.7 (3)C6'—C11'—H11'120.2
C10—C11—H11120.2N2'—C18'—C2'179.5 (3)
C6—C11—H11120.2C20'—C19'—C20A52.8 (5)
N2—C18—C2177.2 (3)C20'—C19'—O1'110.3 (4)
O1—C19—C20107.6 (2)C20A—C19'—O1'116.7 (5)
O1—C19—H19A110.2C20'—C19'—H19C109.6
C20—C19—H19A110.2C20A—C19'—H19C57.9
O1—C19—H19B110.2O1'—C19'—H19C109.6
C20—C19—H19B110.2C20'—C19'—H19D109.6
H19A—C19—H19B108.5C20A—C19'—H19D133.7
C19—C20—H20A109.5O1'—C19'—H19D109.6
C19—C20—H20B109.5H19C—C19'—H19D108.1
H20A—C20—H20B109.5C19'—C20'—H20D109.5
C19—C20—H20C109.5C19'—C20'—H20E109.5
H20A—C20—H20C109.5H20D—C20'—H20E109.5
H20B—C20—H20C109.5C19'—C20'—H20F109.5
C1'—O1'—C19'119.0 (3)H20D—C20'—H20F109.5
C1'—N1'—C5'117.6 (2)H20E—C20'—H20F109.5
C1—N1—C5—C43.7 (3)C1'—N1'—C5'—C12'179.7 (2)
C1—N1—C5—C12175.2 (2)N1'—C5'—C4'—C3'2.6 (3)
N1—C5—C4—C35.3 (4)C12'—C5'—C4'—C3'178.7 (2)
C12—C5—C4—C3173.4 (2)C5'—C4'—C3'—C2'1.7 (3)
C5—C4—C3—C21.0 (3)C5'—C4'—C3'—C6'178.0 (2)
C5—C4—C3—C6179.2 (2)C4'—C3'—C2'—C1'0.6 (4)
C4—C3—C2—C14.6 (3)C6'—C3'—C2'—C1'179.7 (2)
C6—C3—C2—C1175.3 (2)C4'—C3'—C2'—C18'177.2 (2)
C4—C3—C2—C18174.3 (2)C6'—C3'—C2'—C18'3.2 (4)
C6—C3—C2—C185.9 (4)C5'—N1'—C1'—O1'178.8 (2)
C5—N1—C1—O1177.8 (2)C5'—N1'—C1'—C2'1.5 (4)
C5—N1—C1—C22.3 (3)C19'—O1'—C1'—N1'0.6 (4)
C19—O1—C1—N18.1 (3)C19'—O1'—C1'—C2'179.1 (3)
C19—O1—C1—C2172.0 (2)C3'—C2'—C1'—N1'2.3 (4)
C3—C2—C1—N16.5 (4)C18'—C2'—C1'—N1'179.1 (3)
C18—C2—C1—N1172.4 (2)C3'—C2'—C1'—O1'177.9 (2)
C3—C2—C1—O1173.6 (2)C18'—C2'—C1'—O1'1.1 (4)
C18—C2—C1—O17.5 (3)N1'—C5'—C12'—C17'156.8 (3)
N1—C5—C12—C17154.8 (2)C4'—C5'—C12'—C17'24.4 (4)
C4—C5—C12—C1724.0 (4)N1'—C5'—C12'—C13'21.0 (4)
N1—C5—C12—C1323.8 (4)C4'—C5'—C12'—C13'157.8 (2)
C4—C5—C12—C13157.3 (3)C17'—C12'—C13'—C14'1.4 (4)
C17—C12—C13—C140.4 (5)C5'—C12'—C13'—C14'179.3 (3)
C5—C12—C13—C14178.3 (3)C12'—C13'—C14'—C15'0.2 (5)
C12—C13—C14—C150.7 (6)C13'—C14'—C15'—C16'1.7 (6)
C13—C14—C15—C160.7 (6)C14'—C15'—C16'—C17'1.7 (6)
C14—C15—C16—C170.6 (5)C13'—C12'—C17'—C16'1.4 (5)
C13—C12—C17—C160.2 (4)C5'—C12'—C17'—C16'179.3 (3)
C5—C12—C17—C16178.4 (3)C15'—C16'—C17'—C12'0.1 (5)
C15—C16—C17—C120.3 (5)C2'—C3'—C6'—C7'141.8 (3)
C4—C3—C6—C11142.1 (2)C4'—C3'—C6'—C7'38.6 (3)
C2—C3—C6—C1137.8 (3)C2'—C3'—C6'—C11'41.7 (4)
C4—C3—C6—C735.5 (3)C4'—C3'—C6'—C11'137.9 (3)
C2—C3—C6—C7144.7 (2)C11'—C6'—C7'—C8'0.9 (4)
C11—C6—C7—C81.7 (4)C3'—C6'—C7'—C8'175.6 (3)
C3—C6—C7—C8179.3 (2)C6'—C7'—C8'—C9'0.5 (5)
C6—C7—C8—C91.6 (4)C7'—C8'—C9'—C10'2.0 (6)
C7—C8—C9—C100.8 (5)C8'—C9'—C10'—C11'1.9 (6)
C8—C9—C10—C110.1 (5)C9'—C10'—C11'—C6'0.4 (5)
C9—C10—C11—C60.2 (4)C7'—C6'—C11'—C10'1.0 (4)
C7—C6—C11—C101.0 (4)C3'—C6'—C11'—C10'175.6 (2)
C3—C6—C11—C10178.6 (2)C1'—O1'—C19'—C20'94.1 (6)
C1—O1—C19—C20170.1 (2)C1'—O1'—C19'—C20A151.7 (9)
C1'—N1'—C5'—C4'0.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19D···N10.972.342.709 (5)102
C15—H15···N2i0.932.553.399 (4)153
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC20H16N2O
Mr300.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.5542 (10), 32.027 (3), 12.3910 (7)
β (°) 104.493 (3)
V3)3286.6 (5)
Z4
Radiation typeCu Kα
µ (mm1)0.60
Crystal size (mm)0.2 × 0.1 × 0.1
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
ψ scan
Tmin, Tmax0.930, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
6001, 6001, 3150
Rint0.061
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.160, 1.02
No. of reflections5612
No. of parameters426
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.21

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), Please provide missing details, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1965) and PLATON (Spek, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C11.336 (3)O1'—C19'1.431 (4)
O1—C191.463 (3)N1'—C1'1.299 (3)
N1—C11.313 (3)N2'—C18'1.133 (4)
N2—C181.142 (3)C2'—C18'1.444 (4)
C2—C181.437 (3)C19'—C20'1.337 (6)
C19—C201.477 (4)C19'—C20A1.394 (8)
O1'—C1'1.350 (3)
C1—O1—C19117.81 (19)C1'—O1'—C19'119.0 (3)
C1—N1—C5118.1 (2)C1'—N1'—C5'117.6 (2)
N1—C1—C2123.9 (2)N1'—C1'—C2'124.6 (3)
N2—C18—C2177.2 (3)N2'—C18'—C2'179.5 (3)
O1—C19—C20107.6 (2)C20'—C19'—O1'110.3 (4)
N1—C5—C12—C17154.8 (2)N1'—C5'—C12'—C17'156.8 (3)
C4—C3—C6—C11142.1 (2)C2'—C3'—C6'—C11'41.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19'—H19D···N1'0.972.342.709 (5)102
C15'—H15'···N2i0.932.553.399 (4)153
Symmetry code: (i) x, y+3/2, z1/2.
 

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