(E)-4-Meth­oxy-3,5-dimethyl-2-[(3-nitro­phen­yl)ethen­yl]pyridine

In the crystal of the title compound, C₁₆H₁₆N₂O₃, weak C—H...O hydrogen bonds involving the nitro group as acceptor form chains extending in the b-axis direction. The chains are arranged into layers by π–π stacking inter­actions along the c-axis direction between the substituted pyridine rings, separated by 3.624 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.104
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.007 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         29 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Note

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

   1 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
   3 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

---

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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-4-Methoxy-3,5-dimethyl-2-[(3-nitrophenyl)ethenyl]pyridine

Crystal data

C16H16N2O3	F(000) = 600
Mr = 284.31	Dx = 1.351 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 23.3174 (7) Å	Cell parameters from 7563 reflections
b = 8.2979 (2) Å	θ = 3.8–73.2°
c = 7.2260 (2) Å	µ = 0.78 mm^−1
β = 90.899 (1)°	T = 150 K
V = 1397.95 (7) Å^3	Plate, colourless
Z = 4	0.25 × 0.16 × 0.01 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2764 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2395 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4167 pixels mm^-1	θmax = 73.3°, θmin = 3.8°
ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→9
Tmin = 0.87, Tmax = 0.99	l = −8→8
10335 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)] = 0.039	All H-atom parameters refined
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.417P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2764 reflections	Δρmax = 0.23 e Å^−3
255 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (3)

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

	x	y	z	Uiso*/Ueq
O1	0.95105 (5)	0.03936 (13)	0.34676 (19)	0.0474 (3)
O2	0.86494 (5)	−0.00204 (12)	0.44015 (18)	0.0428 (3)
O3	0.60432 (4)	1.08094 (11)	0.66857 (13)	0.0278 (2)
N1	0.66199 (4)	0.60746 (13)	0.65809 (15)	0.0247 (2)
N2	0.90441 (5)	0.08754 (14)	0.39837 (17)	0.0308 (3)
C1	0.83106 (5)	0.48038 (15)	0.48252 (18)	0.0247 (3)
C2	0.84183 (5)	0.31514 (15)	0.46961 (18)	0.0246 (3)
H2	0.8130 (7)	0.236 (2)	0.502 (2)	0.031 (4)*
C3	0.89481 (5)	0.26256 (15)	0.41017 (18)	0.0254 (3)
C4	0.93826 (6)	0.36645 (18)	0.3615 (2)	0.0316 (3)
H4	0.9740 (7)	0.326 (2)	0.324 (2)	0.036 (4)*
C5	0.92717 (6)	0.53084 (18)	0.3736 (2)	0.0366 (4)
H5	0.9565 (8)	0.605 (2)	0.343 (2)	0.044 (5)*
C6	0.87477 (6)	0.58745 (17)	0.4331 (2)	0.0327 (3)
H6	0.8689 (8)	0.703 (2)	0.434 (2)	0.043 (5)*
C7	0.77435 (5)	0.53257 (16)	0.54498 (19)	0.0260 (3)
H7	0.7471 (7)	0.4469 (19)	0.576 (2)	0.030 (4)*
C8	0.75595 (5)	0.68419 (16)	0.55851 (18)	0.0256 (3)
H8	0.7825 (7)	0.773 (2)	0.531 (2)	0.040 (5)*
C9	0.69782 (5)	0.72919 (15)	0.61500 (17)	0.0222 (3)
C10	0.68107 (5)	0.89220 (15)	0.61999 (17)	0.0226 (3)
C11	0.62485 (5)	0.92452 (15)	0.67111 (17)	0.0228 (3)
C12	0.58704 (5)	0.80139 (15)	0.71531 (17)	0.0240 (3)
C13	0.60879 (5)	0.64531 (15)	0.70639 (19)	0.0253 (3)
H13	0.5831 (6)	0.5569 (19)	0.736 (2)	0.024 (4)*
C14	0.72122 (6)	1.02562 (16)	0.5674 (2)	0.0282 (3)
H14A	0.7019 (11)	1.132 (3)	0.571 (3)	0.076 (7)*
H14B	0.7544 (8)	1.032 (2)	0.652 (3)	0.048 (5)*
H14C	0.7363 (9)	1.009 (2)	0.444 (3)	0.055 (6)*
C15	0.61979 (8)	1.17496 (18)	0.8279 (2)	0.0386 (4)
H15A	0.6201 (11)	1.282 (3)	0.789 (4)	0.084 (8)*
H15B	0.5878 (11)	1.164 (3)	0.920 (4)	0.084 (8)*
H15C	0.6548 (10)	1.142 (3)	0.881 (3)	0.060 (6)*
C16	0.52598 (6)	0.83394 (18)	0.7665 (2)	0.0319 (3)
H16A	0.5035 (8)	0.882 (2)	0.661 (3)	0.048 (5)*
H16B	0.5240 (8)	0.909 (2)	0.874 (3)	0.053 (5)*
H16C	0.5066 (8)	0.732 (2)	0.800 (2)	0.045 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0351 (6)	0.0367 (6)	0.0708 (8)	0.0121 (5)	0.0170 (5)	−0.0044 (6)
O2	0.0385 (6)	0.0243 (5)	0.0660 (8)	−0.0005 (4)	0.0125 (5)	0.0002 (5)
O3	0.0305 (5)	0.0214 (4)	0.0314 (5)	0.0054 (4)	−0.0024 (4)	−0.0019 (4)
N1	0.0239 (5)	0.0224 (5)	0.0279 (6)	0.0002 (4)	0.0024 (4)	−0.0011 (4)
N2	0.0292 (6)	0.0270 (6)	0.0362 (6)	0.0054 (5)	0.0045 (5)	−0.0013 (5)
C1	0.0226 (6)	0.0245 (6)	0.0271 (6)	0.0007 (5)	0.0026 (5)	−0.0006 (5)
C2	0.0220 (6)	0.0242 (6)	0.0278 (6)	−0.0008 (5)	0.0039 (5)	0.0001 (5)
C3	0.0249 (6)	0.0230 (6)	0.0283 (6)	0.0019 (5)	0.0031 (5)	−0.0014 (5)
C4	0.0216 (6)	0.0335 (7)	0.0399 (8)	0.0014 (5)	0.0082 (5)	−0.0031 (6)
C5	0.0274 (7)	0.0300 (7)	0.0528 (9)	−0.0049 (6)	0.0114 (6)	−0.0008 (7)
C6	0.0284 (6)	0.0241 (6)	0.0457 (8)	−0.0006 (5)	0.0080 (6)	−0.0004 (6)
C7	0.0227 (6)	0.0261 (6)	0.0292 (7)	0.0002 (5)	0.0031 (5)	−0.0005 (5)
C8	0.0225 (6)	0.0258 (6)	0.0285 (7)	0.0004 (5)	0.0032 (5)	−0.0004 (5)
C9	0.0225 (6)	0.0221 (6)	0.0221 (6)	0.0001 (5)	0.0009 (5)	−0.0005 (5)
C10	0.0238 (6)	0.0224 (6)	0.0217 (6)	−0.0005 (5)	−0.0005 (5)	−0.0001 (5)
C11	0.0252 (6)	0.0213 (6)	0.0218 (6)	0.0029 (5)	−0.0013 (5)	−0.0010 (5)
C12	0.0226 (6)	0.0256 (6)	0.0237 (6)	0.0023 (5)	0.0018 (5)	−0.0008 (5)
C13	0.0233 (6)	0.0237 (6)	0.0291 (7)	−0.0019 (5)	0.0024 (5)	−0.0003 (5)
C14	0.0263 (6)	0.0232 (6)	0.0352 (7)	−0.0017 (5)	0.0020 (6)	0.0023 (6)
C15	0.0518 (9)	0.0255 (7)	0.0382 (8)	0.0090 (6)	−0.0106 (7)	−0.0078 (6)
C16	0.0242 (6)	0.0324 (7)	0.0393 (8)	0.0024 (5)	0.0059 (6)	−0.0007 (6)

Geometric parameters (Å, º)

O1—N2	1.2224 (15)	C7—H7	0.982 (16)
O2—N2	1.2246 (16)	C8—C9	1.4699 (17)
O3—C11	1.3835 (14)	C8—H8	0.982 (18)
O3—C15	1.4320 (17)	C9—C10	1.4084 (17)
N1—C13	1.3316 (16)	C10—C11	1.3936 (17)
N1—C9	1.3503 (16)	C10—C14	1.5026 (17)
N2—C3	1.4722 (17)	C11—C12	1.3900 (18)
C1—C2	1.3973 (17)	C12—C13	1.3928 (17)
C1—C6	1.4025 (18)	C12—C16	1.5011 (17)
C1—C7	1.4693 (17)	C13—H13	0.972 (15)
C2—C3	1.3848 (17)	C14—H14A	0.99 (2)
C2—H2	0.968 (17)	C14—H14B	0.98 (2)
C3—C4	1.3802 (19)	C14—H14C	0.97 (2)
C4—C5	1.391 (2)	C15—H15A	0.93 (3)
C4—H4	0.942 (17)	C15—H15B	1.01 (3)
C5—C6	1.3838 (19)	C15—H15C	0.94 (2)
C5—H5	0.949 (19)	C16—H16A	1.00 (2)
C6—H6	0.965 (19)	C16—H16B	1.00 (2)
C7—C8	1.3333 (18)	C16—H16C	0.99 (2)
C11—O3—C15	114.69 (10)	C10—C9—C8	120.55 (11)
C13—N1—C9	117.79 (11)	C11—C10—C9	117.00 (11)
O1—N2—O2	123.54 (12)	C11—C10—C14	121.17 (11)
O1—N2—C3	118.50 (11)	C9—C10—C14	121.81 (11)
O2—N2—C3	117.96 (11)	O3—C11—C12	118.16 (11)
C2—C1—C6	118.20 (12)	O3—C11—C10	120.26 (11)
C2—C1—C7	118.25 (11)	C12—C11—C10	121.48 (11)
C6—C1—C7	123.55 (12)	C11—C12—C13	116.11 (11)
C3—C2—C1	119.47 (12)	C11—C12—C16	122.13 (11)
C3—C2—H2	119.2 (9)	C13—C12—C16	121.75 (12)
C1—C2—H2	121.4 (9)	N1—C13—C12	124.95 (12)
C4—C3—C2	122.98 (12)	N1—C13—H13	117.3 (9)
C4—C3—N2	119.24 (11)	C12—C13—H13	117.7 (9)
C2—C3—N2	117.78 (11)	C10—C14—H14A	111.2 (14)
C3—C4—C5	117.28 (12)	C10—C14—H14B	111.7 (11)
C3—C4—H4	120.6 (10)	H14A—C14—H14B	107.0 (18)
C5—C4—H4	122.1 (10)	C10—C14—H14C	111.5 (12)
C6—C5—C4	121.22 (13)	H14A—C14—H14C	108.9 (18)
C6—C5—H5	119.8 (11)	H14B—C14—H14C	106.4 (16)
C4—C5—H5	118.9 (11)	O3—C15—H15A	106.2 (16)
C5—C6—C1	120.85 (13)	O3—C15—H15B	107.5 (15)
C5—C6—H6	117.7 (10)	H15A—C15—H15B	107 (2)
C1—C6—H6	121.4 (10)	O3—C15—H15C	112.3 (13)
C8—C7—C1	126.36 (12)	H15A—C15—H15C	113 (2)
C8—C7—H7	117.1 (9)	H15B—C15—H15C	110.7 (19)
C1—C7—H7	116.5 (9)	C12—C16—H16A	111.7 (11)
C7—C8—C9	124.01 (12)	C12—C16—H16B	111.1 (11)
C7—C8—H8	119.0 (10)	H16A—C16—H16B	108.4 (16)
C9—C8—H8	117.0 (10)	C12—C16—H16C	110.3 (11)
N1—C9—C10	122.67 (11)	H16A—C16—H16C	107.0 (15)
N1—C9—C8	116.77 (11)	H16B—C16—H16C	108.2 (15)
C6—C1—C2—C3	0.4 (2)	C7—C8—C9—N1	1.2 (2)
C7—C1—C2—C3	179.66 (12)	C7—C8—C9—C10	−177.88 (13)
C1—C2—C3—C4	−0.3 (2)	N1—C9—C10—C11	−0.35 (18)
C1—C2—C3—N2	−179.96 (12)	C8—C9—C10—C11	178.63 (11)
O1—N2—C3—C4	0.5 (2)	N1—C9—C10—C14	−178.60 (12)
O2—N2—C3—C4	−179.11 (13)	C8—C9—C10—C14	0.38 (19)
O1—N2—C3—C2	−179.74 (13)	C15—O3—C11—C12	102.35 (15)
O2—N2—C3—C2	0.61 (19)	C15—O3—C11—C10	−81.30 (16)
C2—C3—C4—C5	−0.1 (2)	C9—C10—C11—O3	−176.17 (11)
N2—C3—C4—C5	179.58 (13)	C14—C10—C11—O3	2.08 (18)
C3—C4—C5—C6	0.4 (2)	C9—C10—C11—C12	0.05 (18)
C4—C5—C6—C1	−0.2 (3)	C14—C10—C11—C12	178.30 (12)
C2—C1—C6—C5	−0.2 (2)	O3—C11—C12—C13	176.66 (11)
C7—C1—C6—C5	−179.39 (14)	C10—C11—C12—C13	0.36 (18)
C2—C1—C7—C8	−177.22 (14)	O3—C11—C12—C16	−2.31 (18)
C6—C1—C7—C8	2.0 (2)	C10—C11—C12—C16	−178.61 (12)
C1—C7—C8—C9	177.47 (12)	C9—N1—C13—C12	0.3 (2)
C13—N1—C9—C10	0.21 (19)	C11—C12—C13—N1	−0.5 (2)
C13—N1—C9—C8	−178.80 (11)	C16—C12—C13—N1	178.44 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2^i	0.97 (2)	2.45 (2)	3.414 (2)	174 (1)

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