Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of 4-[(prop-2-en-1-yl­oxy)meth­yl]-3,6-bis­(pyridin-2-yl)pyridazine

The title compound consists of a 3,6-bis­(pyridin-2-yl)pyridazine unit linked to a 4-[(prop-2-en-1-yl­oxy)meth­yl] moiety. The pyridine-2-yl rings are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—H...N hydrogen bonds and C—H...π inter­actions link the mol­ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.101
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         35 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         57 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-[(Prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine

Crystal data

C18H16N4O	F(000) = 640
Mr = 304.35	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.9420 (2) Å	Cell parameters from 9267 reflections
b = 15.1130 (3) Å	θ = 4.9–74.5°
c = 11.5829 (3) Å	µ = 0.68 mm^−1
β = 100.132 (1)°	T = 150 K
V = 1540.91 (6) Å^3	Plate, colourless
Z = 4	0.26 × 0.24 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3051 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2688 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4167 pixels mm^-1	θmax = 74.5°, θmin = 4.9°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −18→18
Tmin = 0.86, Tmax = 0.95	l = −14→13
11678 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	All H-atom parameters refined
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.3637P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3051 reflections	Δρmax = 0.18 e Å^−3
273 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual space	Extinction coefficient: 0.0046 (5)

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	0.27225 (10)	0.47749 (5)	0.30640 (7)	0.0319 (2)
N1	0.19512 (11)	0.50876 (6)	0.70191 (8)	0.0283 (2)
N2	0.27872 (11)	0.58215 (6)	0.70850 (8)	0.0283 (2)
N3	0.49183 (11)	0.71463 (6)	0.53716 (8)	0.0299 (2)
N4	0.07708 (13)	0.31558 (7)	0.53457 (10)	0.0370 (3)
C1	0.17076 (12)	0.45900 (7)	0.60429 (10)	0.0249 (2)
C2	0.23110 (12)	0.48225 (7)	0.50338 (10)	0.0244 (2)
C3	0.31696 (12)	0.55846 (7)	0.51158 (10)	0.0257 (2)
H3	0.3616 (15)	0.5785 (9)	0.4416 (12)	0.030 (3)*
C4	0.33924 (12)	0.60672 (7)	0.61566 (9)	0.0244 (2)
C5	0.43278 (12)	0.68871 (7)	0.63070 (10)	0.0250 (2)
C6	0.45861 (13)	0.73441 (8)	0.73683 (10)	0.0292 (3)
H6	0.4125 (17)	0.7131 (10)	0.8002 (13)	0.040 (4)*
C7	0.54897 (14)	0.80913 (8)	0.74716 (11)	0.0329 (3)
H7	0.5668 (18)	0.8438 (11)	0.8229 (15)	0.049 (4)*
C8	0.61156 (14)	0.83614 (8)	0.65191 (11)	0.0326 (3)
H8	0.6740 (17)	0.8887 (10)	0.6564 (14)	0.042 (4)*
C9	0.57918 (14)	0.78700 (8)	0.54977 (11)	0.0323 (3)
H9	0.6207 (17)	0.8041 (10)	0.4814 (14)	0.043 (4)*
C10	0.07702 (12)	0.37891 (7)	0.61505 (10)	0.0269 (3)
C11	−0.00417 (14)	0.37100 (9)	0.70670 (11)	0.0346 (3)
H11	−0.0048 (18)	0.4190 (11)	0.7619 (14)	0.044 (4)*
C12	−0.08744 (15)	0.29497 (9)	0.71477 (12)	0.0404 (3)
H12	−0.147 (2)	0.2897 (11)	0.7774 (16)	0.058 (5)*
C13	−0.08794 (16)	0.22904 (9)	0.63254 (12)	0.0405 (3)
H13	−0.1415 (19)	0.1766 (12)	0.6368 (14)	0.050 (4)*
C14	−0.00414 (18)	0.24243 (9)	0.54512 (13)	0.0440 (3)
H14	−0.0035 (19)	0.1969 (11)	0.4852 (15)	0.052 (5)*
C15	0.20351 (13)	0.43087 (8)	0.39007 (10)	0.0279 (3)
H15A	0.0898 (16)	0.4252 (9)	0.3600 (12)	0.032 (3)*
H15B	0.2466 (16)	0.3702 (10)	0.4016 (12)	0.036 (4)*
C16	0.23624 (15)	0.43750 (8)	0.19364 (10)	0.0321 (3)
H16A	0.1233 (17)	0.4420 (9)	0.1637 (13)	0.037 (4)*
H16B	0.2670 (16)	0.3739 (10)	0.1992 (13)	0.038 (4)*
C17	0.32018 (17)	0.48569 (9)	0.11329 (11)	0.0377 (3)
H17	0.436 (2)	0.4884 (12)	0.1409 (17)	0.065 (5)*
C18	0.2574 (2)	0.51972 (11)	0.01194 (13)	0.0497 (4)
H18A	0.150 (2)	0.5087 (12)	−0.0128 (17)	0.065 (6)*
H18B	0.314 (2)	0.5515 (13)	−0.0442 (18)	0.068 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0418 (5)	0.0330 (4)	0.0225 (4)	−0.0060 (3)	0.0099 (3)	−0.0033 (3)
N1	0.0316 (5)	0.0278 (5)	0.0259 (5)	−0.0019 (4)	0.0065 (4)	0.0011 (4)
N2	0.0321 (5)	0.0283 (5)	0.0251 (5)	−0.0025 (4)	0.0070 (4)	0.0001 (4)
N3	0.0351 (5)	0.0306 (5)	0.0249 (5)	−0.0051 (4)	0.0079 (4)	−0.0004 (4)
N4	0.0503 (7)	0.0280 (5)	0.0348 (6)	−0.0061 (4)	0.0129 (5)	−0.0010 (4)
C1	0.0243 (5)	0.0250 (5)	0.0252 (6)	0.0039 (4)	0.0035 (4)	0.0027 (4)
C2	0.0249 (5)	0.0246 (5)	0.0236 (6)	0.0045 (4)	0.0034 (4)	0.0014 (4)
C3	0.0272 (5)	0.0272 (5)	0.0230 (6)	0.0019 (4)	0.0051 (4)	0.0013 (4)
C4	0.0244 (5)	0.0259 (5)	0.0229 (5)	0.0027 (4)	0.0038 (4)	0.0020 (4)
C5	0.0243 (5)	0.0270 (5)	0.0235 (6)	0.0023 (4)	0.0034 (4)	0.0015 (4)
C6	0.0302 (6)	0.0339 (6)	0.0239 (6)	−0.0026 (5)	0.0059 (4)	−0.0009 (4)
C7	0.0361 (6)	0.0348 (6)	0.0274 (6)	−0.0041 (5)	0.0044 (5)	−0.0053 (5)
C8	0.0350 (6)	0.0297 (6)	0.0325 (7)	−0.0060 (5)	0.0047 (5)	−0.0006 (5)
C9	0.0381 (6)	0.0325 (6)	0.0277 (6)	−0.0065 (5)	0.0089 (5)	0.0015 (5)
C10	0.0264 (5)	0.0262 (5)	0.0274 (6)	0.0024 (4)	0.0026 (4)	0.0042 (4)
C11	0.0336 (6)	0.0361 (6)	0.0355 (7)	−0.0049 (5)	0.0101 (5)	−0.0016 (5)
C12	0.0378 (7)	0.0455 (7)	0.0399 (7)	−0.0096 (6)	0.0121 (6)	0.0032 (6)
C13	0.0434 (7)	0.0338 (7)	0.0437 (8)	−0.0110 (6)	0.0059 (6)	0.0055 (5)
C14	0.0603 (9)	0.0310 (6)	0.0424 (8)	−0.0107 (6)	0.0140 (6)	−0.0031 (6)
C15	0.0320 (6)	0.0270 (6)	0.0257 (6)	−0.0007 (4)	0.0079 (5)	−0.0004 (4)
C16	0.0412 (7)	0.0299 (6)	0.0254 (6)	0.0005 (5)	0.0066 (5)	−0.0052 (4)
C17	0.0486 (8)	0.0373 (7)	0.0293 (7)	0.0008 (6)	0.0131 (6)	−0.0040 (5)
C18	0.0689 (11)	0.0476 (8)	0.0355 (8)	0.0083 (7)	0.0170 (7)	0.0059 (6)

Geometric parameters (Å, º)

O1—C15	1.4224 (13)	C8—C9	1.3836 (17)
O1—C16	1.4237 (14)	C8—H8	0.966 (16)
N1—N2	1.3322 (13)	C9—H9	0.968 (15)
N1—C1	1.3434 (15)	C10—C11	1.3926 (17)
N2—C4	1.3386 (14)	C11—C12	1.3813 (18)
N3—C9	1.3370 (15)	C11—H11	0.968 (17)
N3—C5	1.3445 (14)	C12—C13	1.378 (2)
N4—C10	1.3362 (15)	C12—H12	0.974 (17)
N4—C14	1.3400 (17)	C13—C14	1.377 (2)
C1—C2	1.4151 (15)	C13—H13	0.931 (18)
C1—C10	1.4901 (15)	C14—H14	0.978 (17)
C2—C3	1.3782 (15)	C15—H15A	1.019 (14)
C2—C15	1.5075 (15)	C15—H15B	0.994 (15)
C3—C4	1.3930 (15)	C16—C17	1.4851 (18)
C3—H3	1.012 (14)	C16—H16A	1.011 (15)
C4—C5	1.4880 (15)	C16—H16B	0.999 (15)
C5—C6	1.3934 (16)	C17—C18	1.314 (2)
C6—C7	1.3813 (17)	C17—H17	1.03 (2)
C6—H6	0.959 (15)	C18—H18A	0.96 (2)
C7—C8	1.3836 (17)	C18—H18B	1.01 (2)
C7—H7	1.010 (17)
O1···C11^i	3.2992 (16)	C3···C11^i	3.5866 (17)
O1···H3	2.232 (14)	C6···C12^iv	3.5808 (18)
O1···H11^i	2.850 (16)	C8···C10^vi	3.5797 (17)
N1···C8^ii	3.4105 (15)	C11···C15^i	3.5633 (18)
N4···C15	2.7895 (16)	C1···H7^ii	2.925 (17)
N1···H8^ii	2.586 (15)	C6···H16B^v	2.933 (15)
N1···H11	2.441 (16)	C9···H15B^v	2.842 (15)
N1···H15A^i	2.713 (14)	C18···H8^vii	2.920 (16)
N2···H18B^iii	2.86 (2)	H6···H9^viii	2.56 (2)
N2···H13^iv	2.744 (17)	H8···N1^vi	2.586 (16)
N2···H6	2.455 (15)	H11···H16A^i	2.57 (2)
N3···H3	2.522 (14)	H12···C6^ix	2.886 (18)
N3···H15B^v	2.652 (15)	H12···H14^x	2.53 (3)
N4···H15A	2.632 (14)	H13···H18B^xi	2.55 (3)
N4···H15B	2.485 (14)	H15A···H16A	2.36 (2)
C1···C7^ii	3.5853 (17)	H15B···H16B	2.38 (2)
C2···C10^i	3.5420 (15)	H16A···H18A	2.33 (2)
C15—O1—C16	111.09 (9)	N4—C10—C1	117.02 (10)
N2—N1—C1	121.37 (9)	C11—C10—C1	120.65 (10)
N1—N2—C4	119.14 (9)	C12—C11—C10	118.85 (12)
C9—N3—C5	117.07 (10)	C12—C11—H11	120.9 (9)
C10—N4—C14	117.42 (11)	C10—C11—H11	120.3 (10)
N1—C1—C2	121.82 (10)	C13—C12—C11	119.41 (12)
N1—C1—C10	113.24 (10)	C13—C12—H12	121.3 (10)
C2—C1—C10	124.93 (10)	C11—C12—H12	119.3 (10)
C3—C2—C1	116.06 (10)	C14—C13—C12	117.79 (12)
C3—C2—C15	119.63 (10)	C14—C13—H13	121.0 (10)
C1—C2—C15	124.29 (10)	C12—C13—H13	121.2 (10)
C2—C3—C4	119.36 (10)	N4—C14—C13	124.22 (13)
C2—C3—H3	119.3 (8)	N4—C14—H14	116.4 (10)
C4—C3—H3	121.3 (8)	C13—C14—H14	119.4 (10)
N2—C4—C3	122.25 (10)	O1—C15—C2	108.29 (9)
N2—C4—C5	115.80 (10)	O1—C15—H15A	109.5 (8)
C3—C4—C5	121.95 (10)	C2—C15—H15A	110.0 (8)
N3—C5—C6	122.61 (10)	O1—C15—H15B	110.2 (8)
N3—C5—C4	116.15 (10)	C2—C15—H15B	111.0 (8)
C6—C5—C4	121.24 (10)	H15A—C15—H15B	107.9 (11)
C7—C6—C5	119.03 (11)	O1—C16—C17	108.01 (10)
C7—C6—H6	122.1 (9)	O1—C16—H16A	109.7 (8)
C5—C6—H6	118.8 (9)	C17—C16—H16A	109.7 (8)
C6—C7—C8	118.99 (11)	O1—C16—H16B	109.5 (9)
C6—C7—H7	120.0 (9)	C17—C16—H16B	110.4 (8)
C8—C7—H7	121.0 (9)	H16A—C16—H16B	109.5 (12)
C9—C8—C7	118.05 (11)	C18—C17—C16	124.63 (15)
C9—C8—H8	121.2 (9)	C18—C17—H17	120.8 (11)
C7—C8—H8	120.7 (9)	C16—C17—H17	114.5 (11)
N3—C9—C8	124.25 (11)	C17—C18—H18A	116.3 (12)
N3—C9—H9	115.5 (9)	C17—C18—H18B	125.0 (12)
C8—C9—H9	120.3 (9)	H18A—C18—H18B	118.4 (16)
N4—C10—C11	122.32 (11)
C1—N1—N2—C4	0.15 (16)	C5—C6—C7—C8	−0.24 (18)
N2—N1—C1—C2	−0.61 (16)	C6—C7—C8—C9	0.57 (18)
N2—N1—C1—C10	178.92 (9)	C5—N3—C9—C8	−0.14 (18)
N1—C1—C2—C3	0.42 (15)	C7—C8—C9—N3	−0.4 (2)
C10—C1—C2—C3	−179.06 (10)	C14—N4—C10—C11	−0.41 (18)
N1—C1—C2—C15	−177.88 (10)	C14—N4—C10—C1	178.51 (11)
C10—C1—C2—C15	2.64 (17)	N1—C1—C10—N4	−164.56 (10)
C1—C2—C3—C4	0.20 (15)	C2—C1—C10—N4	14.96 (16)
C15—C2—C3—C4	178.58 (10)	N1—C1—C10—C11	14.38 (15)
N1—N2—C4—C3	0.49 (16)	C2—C1—C10—C11	−166.10 (11)
N1—N2—C4—C5	−179.18 (9)	N4—C10—C11—C12	0.07 (19)
C2—C3—C4—N2	−0.66 (16)	C1—C10—C11—C12	−178.81 (11)
C2—C3—C4—C5	179.00 (10)	C10—C11—C12—C13	0.1 (2)
C9—N3—C5—C6	0.51 (17)	C11—C12—C13—C14	0.0 (2)
C9—N3—C5—C4	−178.47 (10)	C10—N4—C14—C13	0.6 (2)
N2—C4—C5—N3	−178.91 (10)	C12—C13—C14—N4	−0.4 (2)
C3—C4—C5—N3	1.41 (15)	C16—O1—C15—C2	−173.64 (9)
N2—C4—C5—C6	2.09 (15)	C3—C2—C15—O1	−2.59 (14)
C3—C4—C5—C6	−177.59 (10)	C1—C2—C15—O1	175.66 (9)
N3—C5—C6—C7	−0.32 (18)	C15—O1—C16—C17	−176.11 (10)
C4—C5—C6—C7	178.61 (10)	O1—C16—C17—C18	−126.92 (14)

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

Hydrogen-bond geometry (Å, º)

Cg is the centroid of pyridine ring B (N3/C5—C9).

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1^vi	0.966 (16)	2.585 (16)	3.4104 (15)	143.4 (12)
C15—H15B···Cg^v	0.994 (15)	2.990 (15)	3.8760 (13)	149.0 (11)

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