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The crystal structure of the heterocyclic com­pound 2-(4-meth­oxy­phen­yl)-7-phenyl­pyra­zolo­[1,5-c]py­rimi­dine, C19H15N3O, has been determined and its self-assembly on the surface of graphite has been examined using atomic force microscopy (AFM). The title com­pound crystallized in the monoclinic space group P21/c, with two independent mol­ecules in the asymmetric unit. The packing of the L-shaped mol­ecules in the crystal is governed by arene inter­actions, in the absence of any conventional hydrogen-bonding inter­actions. The packing arrangement reveals four types of dimeric motifs stabilized by π–π and C—H...π inter­actions. At low coverage, mol­ecules assemble into long needle-like islands on the graphite surface. High-resolution AFM images reveal that the mol­ecules inter­act through weak noncovalent inter­actions between the aromatic H atoms and the meth­oxy O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621011232/vp3019sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621011232/vp3019Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621011232/vp3019sup3.pdf
Alternative model (Model-2) for the molecular adlayer and the optimized geometry

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621011232/vp3019Isup4.cml
Supplementary material

CCDC reference: 2071327

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

2-(4-Methoxyphenyl)-7-phenylpyrazolo[1,5-c]pyrimidine top
Crystal data top
C19H15N3OF(000) = 1264
Mr = 301.34Dx = 1.321 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.7626 (4) ÅCell parameters from 22699 reflections
b = 36.693 (2) Åθ = 1.5–26.4°
c = 14.3279 (10) ŵ = 0.08 mm1
β = 90.07 (1)°T = 296 K
V = 3029.6 (3) Å3Platy, colorless
Z = 80.3 × 0.1 × 0.01 mm
Data collection top
Bruker APEX CCD
diffractometer
Rint = 0.064
Radiation source: Fine-focus sealed tubeθmax = 26.4°, θmin = 1.5°
ω scansh = 77
22699 measured reflectionsk = 4544
5727 independent reflectionsl = 1717
2694 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046 w = 1/[σ2(Fo2) + (0.0478P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 0.85Δρmax = 0.19 e Å3
5727 reflectionsΔρmin = 0.18 e Å3
416 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0033 (4)
Primary atom site location: structure-invariant direct methods
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8487 (3)0.20497 (4)0.23238 (10)0.0598 (4)
C301.3534 (4)0.22899 (6)0.98529 (14)0.0454 (5)
N41.1510 (3)0.39648 (5)0.94352 (12)0.0518 (5)
O21.3545 (3)0.19176 (4)0.98453 (10)0.0579 (4)
N20.6303 (3)0.37302 (5)0.29945 (12)0.0522 (5)
N51.1258 (3)0.36008 (5)0.92836 (12)0.0511 (5)
C271.3143 (4)0.30474 (6)0.98104 (14)0.0466 (5)
C261.2927 (4)0.34452 (6)0.98067 (14)0.0484 (5)
C70.8123 (3)0.31784 (6)0.24246 (13)0.0473 (5)
C60.7922 (4)0.35763 (6)0.24576 (14)0.0498 (5)
C291.5272 (4)0.25042 (6)1.02269 (14)0.0531 (6)
H0111.65740.23971.04950.064*
C100.8499 (4)0.24230 (6)0.23371 (14)0.0465 (5)
C110.6588 (4)0.25829 (6)0.27470 (14)0.0498 (5)
H0130.54200.24370.29960.060*
N10.6557 (3)0.40952 (5)0.28593 (12)0.0547 (5)
C40.8340 (4)0.41691 (7)0.22376 (17)0.0630 (6)
C281.5065 (4)0.28785 (6)1.02011 (14)0.0540 (6)
H0161.62440.30211.04520.065*
C241.3332 (4)0.40365 (7)1.00459 (16)0.0575 (6)
C120.6402 (4)0.29544 (6)0.27897 (13)0.0497 (5)
H0180.51040.30590.30670.060*
C140.3436 (4)0.42863 (6)0.39638 (16)0.0552 (6)
C340.8304 (4)0.41607 (6)0.83628 (15)0.0519 (6)
N61.0639 (4)0.45767 (5)0.92405 (15)0.0688 (6)
C311.1611 (4)0.24536 (6)0.94523 (14)0.0480 (5)
H0221.04410.23110.91950.058*
C81.0031 (4)0.30128 (6)0.20213 (14)0.0534 (6)
H0231.12100.31570.17780.064*
C10.5307 (4)0.43665 (6)0.32902 (17)0.0605 (6)
C321.1426 (4)0.28256 (6)0.94333 (14)0.0473 (5)
H0251.01250.29320.91620.057*
C331.5527 (5)0.17394 (7)1.02316 (18)0.0757 (7)
H02A1.53300.14801.01860.114*
H02B1.68890.18110.98930.114*
H02C1.56940.18071.08750.114*
C180.0503 (4)0.39145 (7)0.46527 (19)0.0750 (8)
H0270.02590.36910.46860.090*
C50.9207 (4)0.38373 (6)0.19765 (16)0.0610 (6)
H0281.04150.37940.15610.073*
C170.0167 (5)0.41912 (8)0.52192 (19)0.0788 (8)
H0290.13960.41600.56320.095*
C390.7222 (4)0.38254 (6)0.82604 (16)0.0578 (6)
H0300.77120.36280.86190.069*
C91.0225 (4)0.26386 (6)0.19722 (14)0.0530 (6)
H0311.15170.25330.16940.064*
C251.4248 (4)0.37056 (6)1.02895 (16)0.0589 (6)
H0321.54870.36621.06910.071*
C360.5723 (5)0.43964 (7)0.71826 (19)0.0778 (8)
H0330.52370.45910.68150.093*
C190.2287 (4)0.39592 (6)0.40316 (17)0.0620 (6)
H0340.27250.37660.36510.074*
C350.7492 (5)0.44448 (7)0.78109 (19)0.0712 (7)
H0350.81670.46740.78690.085*
C211.0200 (4)0.42381 (6)0.90320 (16)0.0549 (6)
C30.8788 (5)0.45372 (7)0.20540 (19)0.0820 (8)
H0370.99570.46060.16430.098*
C150.2757 (5)0.45661 (7)0.4554 (2)0.0842 (8)
H0380.35140.47900.45260.101*
C131.0464 (4)0.18693 (7)0.19591 (18)0.0768 (8)
H03A1.02330.16100.19900.115*
H03B1.06900.19410.13210.115*
H03C1.18070.19340.23190.115*
N30.5776 (4)0.47053 (5)0.31016 (16)0.0820 (7)
C231.3771 (5)0.44045 (7)1.02523 (18)0.0726 (7)
H0411.49600.44721.06570.087*
C380.5423 (4)0.37807 (6)0.76320 (18)0.0678 (7)
H0420.47130.35540.75740.081*
C370.4672 (5)0.40661 (7)0.70919 (19)0.0744 (7)
H0430.34610.40340.66700.089*
C221.2402 (5)0.46567 (7)0.9842 (2)0.0795 (8)
H0441.26800.49010.99790.095*
C160.0984 (6)0.45174 (8)0.5178 (2)0.0919 (9)
H0450.05610.47060.55750.110*
C20.7485 (6)0.47879 (7)0.2488 (2)0.0951 (10)
H0490.77700.50320.23610.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0581 (9)0.0594 (10)0.0619 (10)0.0064 (8)0.0054 (8)0.0076 (8)
C300.0482 (12)0.0494 (14)0.0387 (11)0.0055 (11)0.0044 (10)0.0005 (10)
N40.0539 (11)0.0452 (12)0.0563 (12)0.0066 (9)0.0075 (10)0.0054 (9)
O20.0597 (9)0.0549 (10)0.0592 (10)0.0099 (8)0.0029 (8)0.0028 (8)
N20.0524 (11)0.0470 (11)0.0572 (11)0.0007 (9)0.0059 (9)0.0057 (9)
N50.0554 (11)0.0431 (11)0.0548 (11)0.0019 (9)0.0041 (9)0.0020 (9)
C270.0450 (12)0.0550 (14)0.0397 (12)0.0005 (11)0.0031 (10)0.0029 (10)
C260.0466 (12)0.0566 (15)0.0419 (12)0.0032 (11)0.0032 (10)0.0030 (11)
C70.0437 (12)0.0598 (14)0.0384 (12)0.0012 (10)0.0002 (10)0.0012 (10)
C60.0478 (12)0.0587 (15)0.0429 (13)0.0014 (11)0.0003 (10)0.0049 (10)
C290.0467 (13)0.0660 (16)0.0464 (13)0.0129 (12)0.0069 (11)0.0023 (11)
C100.0484 (12)0.0530 (14)0.0379 (11)0.0060 (11)0.0040 (10)0.0067 (10)
C110.0435 (12)0.0627 (15)0.0433 (12)0.0035 (11)0.0043 (10)0.0040 (11)
N10.0563 (11)0.0515 (12)0.0564 (12)0.0022 (10)0.0067 (10)0.0096 (9)
C40.0626 (15)0.0637 (17)0.0627 (15)0.0063 (13)0.0095 (13)0.0150 (13)
C280.0453 (12)0.0674 (17)0.0494 (13)0.0020 (12)0.0067 (10)0.0094 (12)
C240.0577 (14)0.0593 (16)0.0556 (14)0.0135 (12)0.0059 (12)0.0091 (12)
C120.0445 (12)0.0619 (15)0.0428 (12)0.0054 (11)0.0069 (10)0.0058 (11)
C140.0571 (13)0.0474 (14)0.0613 (15)0.0070 (12)0.0019 (12)0.0087 (11)
C340.0542 (13)0.0422 (13)0.0593 (14)0.0029 (11)0.0104 (11)0.0002 (11)
N60.0782 (14)0.0456 (13)0.0825 (15)0.0086 (11)0.0089 (12)0.0077 (11)
C310.0443 (12)0.0523 (14)0.0473 (13)0.0019 (11)0.0016 (10)0.0027 (10)
C80.0459 (12)0.0670 (16)0.0472 (13)0.0020 (11)0.0080 (10)0.0012 (11)
C10.0639 (15)0.0458 (14)0.0719 (16)0.0045 (12)0.0047 (13)0.0051 (12)
C320.0431 (11)0.0539 (14)0.0450 (13)0.0024 (10)0.0015 (10)0.0043 (10)
C330.0801 (18)0.0672 (17)0.0797 (18)0.0252 (14)0.0122 (15)0.0064 (14)
C180.0561 (15)0.0756 (19)0.093 (2)0.0097 (14)0.0114 (15)0.0090 (16)
C50.0583 (14)0.0713 (17)0.0535 (14)0.0029 (13)0.0115 (12)0.0107 (12)
C170.0667 (17)0.083 (2)0.086 (2)0.0124 (16)0.0194 (15)0.0018 (16)
C390.0535 (14)0.0491 (14)0.0708 (16)0.0016 (11)0.0008 (13)0.0077 (11)
C90.0425 (12)0.0695 (16)0.0471 (13)0.0057 (11)0.0060 (10)0.0041 (11)
C250.0557 (14)0.0687 (17)0.0524 (14)0.0082 (13)0.0041 (11)0.0075 (12)
C360.0819 (19)0.0644 (19)0.087 (2)0.0194 (15)0.0010 (17)0.0141 (15)
C190.0505 (13)0.0611 (16)0.0745 (17)0.0022 (12)0.0037 (12)0.0065 (12)
C350.0807 (18)0.0496 (16)0.0833 (18)0.0004 (14)0.0080 (16)0.0065 (14)
C210.0621 (15)0.0410 (14)0.0617 (15)0.0033 (12)0.0152 (12)0.0007 (11)
C30.086 (2)0.0701 (19)0.090 (2)0.0131 (16)0.0223 (17)0.0237 (16)
C150.101 (2)0.0535 (16)0.099 (2)0.0023 (15)0.0240 (18)0.0045 (15)
C130.0742 (17)0.0698 (17)0.0865 (19)0.0186 (14)0.0174 (15)0.0097 (14)
N30.0906 (16)0.0501 (14)0.1053 (18)0.0009 (11)0.0233 (14)0.0178 (12)
C230.0767 (18)0.0662 (19)0.0749 (18)0.0213 (15)0.0008 (15)0.0149 (14)
C380.0613 (16)0.0593 (16)0.0828 (19)0.0014 (13)0.0047 (15)0.0023 (14)
C370.0698 (17)0.0733 (19)0.0799 (19)0.0126 (15)0.0074 (15)0.0049 (15)
C220.091 (2)0.0565 (18)0.091 (2)0.0224 (16)0.0099 (17)0.0175 (15)
C160.111 (2)0.076 (2)0.089 (2)0.0215 (19)0.0279 (19)0.0090 (17)
C20.108 (2)0.0565 (18)0.121 (3)0.0088 (18)0.026 (2)0.0243 (17)
Geometric parameters (Å, º) top
O1—C101.370 (2)N6—C221.364 (3)
O1—C131.418 (3)C31—C321.369 (3)
C30—O21.366 (2)C31—H0220.9300
C30—C291.381 (3)C8—C91.379 (3)
C30—C311.385 (3)C8—H0230.9300
N4—N51.361 (2)C1—N31.301 (3)
N4—C211.381 (3)C32—H0250.9300
N4—C241.391 (3)C33—H02A0.9600
O2—C331.427 (3)C33—H02B0.9600
N2—C61.335 (3)C33—H02C0.9600
N2—N11.361 (2)C18—C171.356 (3)
N5—C261.346 (3)C18—C191.370 (3)
C27—C281.386 (3)C18—H0270.9300
C27—C321.390 (3)C5—H0280.9300
C27—C261.465 (3)C17—C161.370 (4)
C26—C251.403 (3)C17—H0290.9300
C7—C81.383 (3)C39—C381.382 (3)
C7—C121.391 (3)C39—H0300.9300
C7—C61.465 (3)C9—H0310.9300
C6—C51.394 (3)C25—H0320.9300
C29—C281.379 (3)C36—C371.361 (3)
C29—H0110.9300C36—C351.371 (4)
C10—C91.375 (3)C36—H0330.9300
C10—C111.380 (3)C19—H0340.9300
C11—C121.369 (3)C35—H0350.9300
C11—H0130.9300C3—C21.341 (4)
N1—C11.375 (3)C3—H0370.9300
N1—C41.388 (3)C15—C161.370 (4)
C4—C51.368 (3)C15—H0380.9300
C4—C31.400 (3)C13—H03A0.9600
C28—H0160.9300C13—H03B0.9600
C24—C251.369 (3)C13—H03C0.9600
C24—C231.405 (3)N3—C21.355 (3)
C12—H0180.9300C23—C221.350 (4)
C14—C191.374 (3)C23—H0410.9300
C14—C151.387 (3)C38—C371.372 (3)
C14—C11.478 (3)C38—H0420.9300
C34—C391.387 (3)C37—H0430.9300
C34—C351.389 (3)C22—H0440.9300
C34—C211.480 (3)C16—H0450.9300
N6—C211.303 (3)C2—H0490.9300
C10—O1—C13117.90 (18)O2—C33—H02B109.5
O2—C30—C29124.72 (19)H02A—C33—H02B109.5
O2—C30—C31115.72 (19)O2—C33—H02C109.5
C29—C30—C31119.6 (2)H02A—C33—H02C109.5
N5—N4—C21125.99 (18)H02B—C33—H02C109.5
N5—N4—C24111.48 (18)C17—C18—C19120.9 (3)
C21—N4—C24122.51 (19)C17—C18—H027119.6
C30—O2—C33117.29 (18)C19—C18—H027119.6
C6—N2—N1104.98 (17)C4—C5—C6106.4 (2)
C26—N5—N4104.55 (17)C4—C5—H028126.8
C28—C27—C32117.6 (2)C6—C5—H028126.8
C28—C27—C26121.0 (2)C18—C17—C16119.4 (3)
C32—C27—C26121.44 (19)C18—C17—H029120.3
N5—C26—C25111.9 (2)C16—C17—H029120.3
N5—C26—C27119.03 (19)C38—C39—C34120.7 (2)
C25—C26—C27129.1 (2)C38—C39—H030119.6
C8—C7—C12117.7 (2)C34—C39—H030119.6
C8—C7—C6120.95 (19)C10—C9—C8119.6 (2)
C12—C7—C6121.34 (19)C10—C9—H031120.2
N2—C6—C5111.5 (2)C8—C9—H031120.2
N2—C6—C7119.69 (19)C24—C25—C26105.6 (2)
C5—C6—C7128.8 (2)C24—C25—H032127.2
C28—C29—C30119.62 (19)C26—C25—H032127.2
C28—C29—H011120.2C37—C36—C35120.6 (2)
C30—C29—H011120.2C37—C36—H033119.7
O1—C10—C9124.99 (19)C35—C36—H033119.7
O1—C10—C11115.28 (19)C18—C19—C14120.8 (2)
C9—C10—C11119.7 (2)C18—C19—H034119.6
C12—C11—C10120.3 (2)C14—C19—H034119.6
C12—C11—H013119.8C36—C35—C34121.8 (2)
C10—C11—H013119.8C36—C35—H035119.1
N2—N1—C1126.28 (18)C34—C35—H035119.1
N2—N1—C4111.32 (18)N6—C21—N4119.4 (2)
C1—N1—C4122.37 (19)N6—C21—C34118.3 (2)
C5—C4—N1105.82 (19)N4—C21—C34122.27 (19)
C5—C4—C3137.7 (2)C2—C3—C4118.1 (3)
N1—C4—C3116.5 (2)C2—C3—H037120.9
C29—C28—C27121.7 (2)C4—C3—H037120.9
C29—C28—H016119.2C16—C15—C14120.8 (3)
C27—C28—H016119.2C16—C15—H038119.6
C25—C24—N4106.5 (2)C14—C15—H038119.6
C25—C24—C23136.8 (3)O1—C13—H03A109.5
N4—C24—C23116.7 (2)O1—C13—H03B109.5
C11—C12—C7121.1 (2)H03A—C13—H03B109.5
C11—C12—H018119.5O1—C13—H03C109.5
C7—C12—H018119.5H03A—C13—H03C109.5
C19—C14—C15117.8 (2)H03B—C13—H03C109.5
C19—C14—C1124.9 (2)C1—N3—C2120.0 (2)
C15—C14—C1117.2 (2)C22—C23—C24117.5 (2)
C39—C34—C35117.0 (2)C22—C23—H041121.2
C39—C34—C21124.8 (2)C24—C23—H041121.2
C35—C34—C21118.2 (2)C37—C38—C39120.9 (2)
C21—N6—C22119.6 (2)C37—C38—H042119.6
C32—C31—C30120.2 (2)C39—C38—H042119.6
C32—C31—H022119.9C36—C37—C38119.1 (3)
C30—C31—H022119.9C36—C37—H043120.5
C9—C8—C7121.6 (2)C38—C37—H043120.5
C9—C8—H023119.2C23—C22—N6124.2 (2)
C7—C8—H023119.2C23—C22—H044117.9
N3—C1—N1119.3 (2)N6—C22—H044117.9
N3—C1—C14118.6 (2)C17—C16—C15120.2 (3)
N1—C1—C14122.1 (2)C17—C16—H045119.9
C31—C32—C27121.38 (19)C15—C16—H045119.9
C31—C32—H025119.3C3—C2—N3123.7 (3)
C27—C32—H025119.3C3—C2—H049118.1
O2—C33—H02A109.5N3—C2—H049118.1
C29—C30—O2—C331.7 (3)C30—C31—C32—C270.0 (3)
C31—C30—O2—C33178.50 (19)C28—C27—C32—C310.5 (3)
C21—N4—N5—C26178.80 (18)C26—C27—C32—C31178.81 (18)
C24—N4—N5—C260.3 (2)N1—C4—C5—C60.4 (3)
N4—N5—C26—C250.1 (2)C3—C4—C5—C6178.8 (3)
N4—N5—C26—C27179.67 (17)N2—C6—C5—C40.4 (3)
C28—C27—C26—N5168.55 (19)C7—C6—C5—C4179.3 (2)
C32—C27—C26—N512.2 (3)C19—C18—C17—C161.0 (4)
C28—C27—C26—C2511.7 (3)C35—C34—C39—C380.2 (3)
C32—C27—C26—C25167.6 (2)C21—C34—C39—C38178.4 (2)
N1—N2—C6—C50.2 (2)O1—C10—C9—C8179.46 (19)
N1—N2—C6—C7179.24 (17)C11—C10—C9—C80.1 (3)
C8—C7—C6—N2167.72 (19)C7—C8—C9—C100.5 (3)
C12—C7—C6—N212.8 (3)N4—C24—C25—C260.2 (2)
C8—C7—C6—C513.5 (3)C23—C24—C25—C26179.7 (3)
C12—C7—C6—C5166.0 (2)N5—C26—C25—C240.0 (2)
O2—C30—C29—C28179.50 (19)C27—C26—C25—C24179.8 (2)
C31—C30—C29—C280.3 (3)C17—C18—C19—C140.3 (4)
C13—O1—C10—C94.1 (3)C15—C14—C19—C181.1 (4)
C13—O1—C10—C11176.52 (19)C1—C14—C19—C18177.2 (2)
O1—C10—C11—C12179.25 (17)C37—C36—C35—C341.2 (4)
C9—C10—C11—C120.2 (3)C39—C34—C35—C360.9 (3)
C6—N2—N1—C1178.0 (2)C21—C34—C35—C36179.2 (2)
C6—N2—N1—C40.1 (2)C22—N6—C21—N40.9 (3)
N2—N1—C4—C50.3 (2)C22—N6—C21—C34178.8 (2)
C1—N1—C4—C5178.3 (2)N5—N4—C21—N6179.84 (19)
N2—N1—C4—C3179.1 (2)C24—N4—C21—N61.5 (3)
C1—N1—C4—C31.1 (3)N5—N4—C21—C340.1 (3)
C30—C29—C28—C270.2 (3)C24—N4—C21—C34178.30 (19)
C32—C27—C28—C290.6 (3)C39—C34—C21—N6161.8 (2)
C26—C27—C28—C29178.67 (18)C35—C34—C21—N616.4 (3)
N5—N4—C24—C250.3 (2)C39—C34—C21—N418.5 (3)
C21—N4—C24—C25178.89 (18)C35—C34—C21—N4163.4 (2)
N5—N4—C24—C23179.65 (19)C5—C4—C3—C2179.0 (3)
C21—N4—C24—C231.1 (3)N1—C4—C3—C20.2 (4)
C10—C11—C12—C70.1 (3)C19—C14—C15—C160.5 (4)
C8—C7—C12—C110.3 (3)C1—C14—C15—C16177.9 (2)
C6—C7—C12—C11179.23 (18)N1—C1—N3—C20.2 (4)
O2—C30—C31—C32179.38 (17)C14—C1—N3—C2179.9 (2)
C29—C30—C31—C320.5 (3)C25—C24—C23—C22179.7 (3)
C12—C7—C8—C90.6 (3)N4—C24—C23—C220.2 (3)
C6—C7—C8—C9178.95 (19)C34—C39—C38—C370.3 (4)
N2—N1—C1—N3178.8 (2)C35—C36—C37—C380.7 (4)
C4—N1—C1—N31.1 (3)C39—C38—C37—C360.0 (4)
N2—N1—C1—C141.3 (3)C24—C23—C22—N60.3 (4)
C4—N1—C1—C14178.9 (2)C21—N6—C22—C230.1 (4)
C19—C14—C1—N3159.8 (2)C18—C17—C16—C151.6 (4)
C15—C14—C1—N318.5 (3)C14—C15—C16—C170.8 (4)
C19—C14—C1—N120.1 (4)C4—C3—C2—N30.7 (5)
C15—C14—C1—N1161.6 (2)C1—N3—C2—C30.8 (5)
Relevant parameters for the intermolecular interactions in the crystal structure of 1 top
ππ interactions
TypeNo.InteractionCg···Cga,b (Å)Interplanar angle γ (°)Symmetry code
Py···Ph1Cg1···Cg43.894 (2)19.6 (1)x+1, y, z
2Cg5···Cg83.849 (2)17.6 (1)x+1, y, z
C—H···π/O interactions
TypeNo.InteractionC···Cg/C···O (Å)\angleC—H···Cg/O (°)Symmetry code
Ph···Ph1C17—H···Cg84.087 (3)136.1x-1, y, z
2C37—H···Cg44.026 (3)144.1x, y, z
OPh···OPh3C11—H···Cg73.645 (3)136.1x-1, -y+1/2, z-1/2
4C12—H···O23.408 (3)b133.2x-1, -y+1/2, z-1/2
5C31—H···Cg33.645 (3)137.6x, -y+1/2, z+1/2
6C32—H···O23.493 (2)c132.4x, -y+1/2, z+1/2
Py···Py7C5—H···Cg63.751 (4)156.6x, y, z-1
8C3—H···Cg54.007 (4)136.2x, y, z-1
9C25—H···Cg23.795 (4)144.3x+1, y, z+1
10C23—H···Cg13.943 (3)147.8x+1, y, z+1
Notes: (a) Cg = centroid and the centroids of the rings are labelled as follows: (MOL-1/MOL-2) Py (six-membered ring) = Cg1/Cg5, Py (five-memebred ring) = Cg2/Cg6, OPh = Cg3/Cg7, Ph = Cg4/Cg8. Atoms labels are as shown in Fig. 1. (b) H···O = 2.70 Å; (c) H···O = 2.79 Å.
Interaction energies of the dimers shown in Fig. 3.
Calculations are performed using DFT GGA/BLYP with van der Waals correction (DFT-D3) implemented in Quantumwise (Schneider et al., 2017)
top
Compound 1Energy of dimer (eV)Energy of monomer (eV)ΔE (eV)
Dimer 1-8881.142-4440.508-0.128
Dimer 2-8881.566-4440.508-0.552
Dimer 3-8881.790-4440.508-0.776
Dimer 4-8882.941-4440.508-1.927
 

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