Crystal structure and Hirshfeld surface analysis of 4-(naphthalen-2-yl)-N-[(Z)-4-propoxybenzyl­idene]-1,3-thia­zol-2-amine

In the crystal, the mol­ecules are linked by weak C—H...π hydrogen bonds and very weak π–π stacking inter­actions. Two-dimensional fingerprint plots show that the largest contributions to the crystal cohesion come from H...H and C...H/H...C inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.087
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2       --C14      .        6.0 s.u.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     38.630 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.036 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.390 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.68 mm
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-(Naphthalen-2-yl)-N-[(Z)-4-propoxybenzylidene]-1,3-thiazol-2-amine

Crystal data

C23H20N2OS	F(000) = 784
Mr = 372.47	Dx = 1.294 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.1636 (11) Å	Cell parameters from 9076 reflections
b = 6.0482 (3) Å	θ = 1.8–31.6°
c = 17.023 (1) Å	µ = 0.18 mm^−1
β = 104.370 (5)°	T = 296 K
V = 1911.32 (19) Å^3	Stick, yellow
Z = 4	0.68 × 0.29 × 0.05 mm

Data collection

STOE IPDS 2 diffractometer	3770 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1951 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.078
rotation method scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −19→23
Tmin = 0.919, Tmax = 0.989	k = −7→7
12341 measured reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0235P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
3770 reflections	Δρmax = 0.12 e Å^−3
245 parameters	Δρmin = −0.16 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.

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

	x	y	z	Uiso*/Ueq
S1	0.72771 (5)	0.01821 (13)	0.45111 (4)	0.0700 (2)
O1	0.57359 (10)	0.7728 (3)	−0.00225 (10)	0.0614 (5)
N1	0.78855 (12)	0.3982 (3)	0.46984 (12)	0.0518 (6)
N2	0.71496 (12)	0.3175 (4)	0.33523 (12)	0.0574 (6)
C15	0.69256 (14)	0.5693 (4)	0.22324 (14)	0.0471 (6)
C6	0.88892 (13)	0.4646 (4)	0.76167 (14)	0.0486 (6)
C8	0.84752 (13)	0.4163 (4)	0.61580 (15)	0.0467 (6)
C11	0.80536 (13)	0.2954 (4)	0.54458 (15)	0.0481 (6)
C7	0.85390 (13)	0.3407 (4)	0.69324 (15)	0.0497 (7)
H7	0.834523	0.203683	0.700743	0.060*
C20	0.63762 (14)	0.4417 (4)	0.17593 (14)	0.0552 (7)
H20	0.626787	0.304989	0.194986	0.066*
C18	0.61554 (13)	0.7170 (4)	0.07205 (14)	0.0494 (7)
C13	0.74782 (15)	0.2697 (4)	0.41597 (15)	0.0526 (7)
C5	0.91907 (14)	0.6724 (4)	0.75068 (16)	0.0520 (7)
C9	0.87997 (14)	0.6206 (4)	0.60570 (16)	0.0542 (7)
H9	0.877676	0.671926	0.553618	0.065*
C19	0.59913 (14)	0.5150 (5)	0.10142 (14)	0.0557 (7)
H19	0.562053	0.428985	0.070646	0.067*
C10	0.91444 (14)	0.7434 (5)	0.67047 (16)	0.0581 (7)
H10	0.935420	0.876963	0.661879	0.070*
C17	0.67016 (15)	0.8446 (5)	0.11727 (16)	0.0570 (7)
H17	0.681829	0.979223	0.097421	0.068*
C14	0.72982 (13)	0.5003 (5)	0.30469 (13)	0.0548 (7)
H14	0.765398	0.591233	0.335507	0.066*
C16	0.70766 (14)	0.7699 (5)	0.19294 (15)	0.0574 (7)
H16	0.744007	0.857655	0.224102	0.069*
C1	0.89269 (14)	0.3919 (5)	0.84200 (16)	0.0592 (7)
H1	0.873907	0.254632	0.850405	0.071*
C12	0.77718 (16)	0.0891 (4)	0.54435 (16)	0.0617 (7)
H12	0.784240	−0.001549	0.589769	0.074*
C2	0.92348 (16)	0.5211 (6)	0.90667 (17)	0.0732 (9)
H2	0.924833	0.472661	0.958877	0.088*
C21	0.59299 (17)	0.9645 (5)	−0.04130 (15)	0.0699 (8)
H21A	0.642670	0.953582	−0.044645	0.084*
H21B	0.587991	1.096221	−0.010673	0.084*
C4	0.95124 (16)	0.7990 (5)	0.81968 (18)	0.0696 (8)
H4	0.971585	0.935292	0.813145	0.084*
C3	0.95304 (17)	0.7257 (6)	0.89530 (18)	0.0761 (9)
H3	0.974148	0.812465	0.939997	0.091*
C22	0.54367 (17)	0.9770 (6)	−0.12479 (17)	0.0846 (10)
H22A	0.554784	1.109652	−0.151339	0.102*
H22B	0.494394	0.989504	−0.120138	0.102*
C23	0.54931 (19)	0.7806 (7)	−0.17675 (18)	0.0990 (12)
H23A	0.518100	0.801144	−0.229840	0.149*
H23B	0.535317	0.649628	−0.152709	0.149*
H23C	0.598123	0.765472	−0.180940	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0868 (6)	0.0596 (5)	0.0589 (4)	−0.0121 (5)	0.0092 (4)	0.0028 (4)
O1	0.0618 (12)	0.0702 (13)	0.0472 (10)	−0.0091 (10)	0.0041 (9)	0.0089 (9)
N1	0.0573 (14)	0.0520 (13)	0.0459 (13)	0.0032 (12)	0.0128 (11)	0.0038 (11)
N2	0.0621 (15)	0.0622 (15)	0.0476 (13)	0.0043 (13)	0.0130 (11)	0.0051 (12)
C15	0.0488 (16)	0.0527 (17)	0.0402 (13)	−0.0014 (14)	0.0117 (12)	−0.0031 (12)
C6	0.0387 (14)	0.0577 (17)	0.0493 (14)	0.0052 (14)	0.0107 (12)	0.0021 (14)
C8	0.0437 (15)	0.0471 (15)	0.0496 (16)	0.0062 (13)	0.0123 (12)	0.0080 (12)
C11	0.0460 (15)	0.0497 (16)	0.0494 (15)	0.0075 (13)	0.0134 (13)	0.0084 (13)
C7	0.0462 (16)	0.0480 (16)	0.0553 (16)	−0.0014 (13)	0.0136 (13)	0.0053 (13)
C20	0.0679 (19)	0.0524 (17)	0.0463 (15)	−0.0097 (15)	0.0159 (14)	0.0010 (13)
C18	0.0457 (15)	0.0578 (18)	0.0437 (15)	−0.0019 (14)	0.0093 (12)	−0.0005 (13)
C13	0.0562 (17)	0.0571 (18)	0.0452 (15)	0.0088 (15)	0.0140 (13)	0.0041 (14)
C5	0.0432 (16)	0.0509 (17)	0.0607 (18)	0.0018 (14)	0.0103 (13)	0.0005 (14)
C9	0.0556 (17)	0.0562 (17)	0.0497 (16)	0.0031 (15)	0.0107 (14)	0.0123 (13)
C19	0.0610 (17)	0.0587 (18)	0.0450 (14)	−0.0186 (16)	0.0085 (13)	−0.0065 (14)
C10	0.0540 (17)	0.0513 (17)	0.0680 (19)	0.0011 (15)	0.0135 (15)	0.0109 (15)
C17	0.0616 (18)	0.0525 (17)	0.0563 (17)	−0.0101 (15)	0.0135 (14)	0.0033 (13)
C14	0.0522 (17)	0.0664 (19)	0.0446 (14)	0.0054 (16)	0.0101 (12)	−0.0054 (15)
C16	0.0545 (17)	0.0619 (19)	0.0534 (17)	−0.0124 (15)	0.0085 (14)	−0.0033 (14)
C1	0.0509 (17)	0.073 (2)	0.0528 (17)	−0.0034 (15)	0.0119 (14)	0.0007 (15)
C12	0.0750 (19)	0.0530 (18)	0.0530 (16)	−0.0017 (17)	0.0079 (14)	0.0076 (14)
C2	0.072 (2)	0.094 (2)	0.0542 (17)	−0.005 (2)	0.0168 (15)	−0.0041 (18)
C21	0.085 (2)	0.0626 (19)	0.0587 (17)	−0.0039 (18)	0.0113 (16)	0.0097 (16)
C4	0.066 (2)	0.067 (2)	0.075 (2)	−0.0083 (17)	0.0159 (17)	−0.0091 (17)
C3	0.076 (2)	0.087 (3)	0.062 (2)	−0.012 (2)	0.0097 (17)	−0.0188 (18)
C22	0.084 (2)	0.099 (3)	0.0621 (19)	−0.002 (2)	0.0013 (17)	0.028 (2)
C23	0.100 (3)	0.139 (3)	0.0546 (19)	−0.035 (3)	0.0144 (19)	−0.005 (2)

Geometric parameters (Å, º)

S1—C12	1.690 (3)	C9—C10	1.357 (4)
S1—C13	1.713 (3)	C9—H9	0.9300
O1—C18	1.362 (3)	C19—H19	0.9300
O1—C21	1.431 (3)	C10—H10	0.9300
N1—C13	1.304 (3)	C17—C16	1.386 (3)
N1—C11	1.380 (3)	C17—H17	0.9300
N2—C14	1.284 (3)	C14—H14	0.9300
N2—C13	1.393 (3)	C16—H16	0.9300
C15—C16	1.377 (3)	C1—C2	1.360 (4)
C15—C20	1.390 (3)	C1—H1	0.9300
C15—C14	1.454 (3)	C12—H12	0.9300
C6—C7	1.407 (3)	C2—C3	1.394 (4)
C6—C5	1.415 (3)	C2—H2	0.9300
C6—C1	1.421 (3)	C21—C22	1.501 (3)
C8—C7	1.372 (3)	C21—H21A	0.9700
C8—C9	1.413 (3)	C21—H21B	0.9700
C8—C11	1.473 (3)	C4—C3	1.354 (4)
C11—C12	1.359 (3)	C4—H4	0.9300
C7—H7	0.9300	C3—H3	0.9300
C20—C19	1.373 (3)	C22—C23	1.501 (4)
C20—H20	0.9300	C22—H22A	0.9700
C18—C17	1.372 (3)	C22—H22B	0.9700
C18—C19	1.386 (3)	C23—H23A	0.9600
C5—C4	1.409 (4)	C23—H23B	0.9600
C5—C10	1.413 (3)	C23—H23C	0.9600
C12—S1—C13	88.87 (14)	C18—C17—H17	120.5
C18—O1—C21	118.1 (2)	C16—C17—H17	120.5
C13—N1—C11	110.0 (2)	N2—C14—C15	121.8 (3)
C14—N2—C13	119.1 (2)	N2—C14—H14	119.1
C16—C15—C20	118.1 (2)	C15—C14—H14	119.1
C16—C15—C14	120.7 (3)	C15—C16—C17	121.8 (3)
C20—C15—C14	121.0 (2)	C15—C16—H16	119.1
C7—C6—C5	119.3 (2)	C17—C16—H16	119.1
C7—C6—C1	122.1 (3)	C2—C1—C6	120.6 (3)
C5—C6—C1	118.5 (2)	C2—C1—H1	119.7
C7—C8—C9	118.1 (2)	C6—C1—H1	119.7
C7—C8—C11	121.7 (2)	C11—C12—S1	111.4 (2)
C9—C8—C11	120.1 (2)	C11—C12—H12	124.3
C12—C11—N1	114.2 (2)	S1—C12—H12	124.3
C12—C11—C8	126.4 (2)	C1—C2—C3	120.5 (3)
N1—C11—C8	119.3 (2)	C1—C2—H2	119.8
C8—C7—C6	121.9 (2)	C3—C2—H2	119.8
C8—C7—H7	119.0	O1—C21—C22	107.8 (2)
C6—C7—H7	119.0	O1—C21—H21A	110.1
C19—C20—C15	120.8 (2)	C22—C21—H21A	110.1
C19—C20—H20	119.6	O1—C21—H21B	110.1
C15—C20—H20	119.6	C22—C21—H21B	110.1
O1—C18—C17	125.0 (2)	H21A—C21—H21B	108.5
O1—C18—C19	114.8 (2)	C3—C4—C5	121.1 (3)
C17—C18—C19	120.2 (2)	C3—C4—H4	119.4
N1—C13—N2	128.0 (2)	C5—C4—H4	119.4
N1—C13—S1	115.54 (19)	C4—C3—C2	120.5 (3)
N2—C13—S1	116.3 (2)	C4—C3—H3	119.8
C4—C5—C10	123.4 (3)	C2—C3—H3	119.8
C4—C5—C6	118.8 (2)	C21—C22—C23	113.4 (3)
C10—C5—C6	117.9 (2)	C21—C22—H22A	108.9
C10—C9—C8	121.3 (2)	C23—C22—H22A	108.9
C10—C9—H9	119.3	C21—C22—H22B	108.9
C8—C9—H9	119.3	C23—C22—H22B	108.9
C20—C19—C18	120.0 (2)	H22A—C22—H22B	107.7
C20—C19—H19	120.0	C22—C23—H23A	109.5
C18—C19—H19	120.0	C22—C23—H23B	109.5
C9—C10—C5	121.3 (3)	H23A—C23—H23B	109.5
C9—C10—H10	119.3	C22—C23—H23C	109.5
C5—C10—H10	119.3	H23A—C23—H23C	109.5
C18—C17—C16	119.0 (2)	H23B—C23—H23C	109.5
C13—N1—C11—C12	0.8 (3)	C15—C20—C19—C18	0.9 (4)
C13—N1—C11—C8	−176.4 (2)	O1—C18—C19—C20	−179.7 (2)
C7—C8—C11—C12	−9.7 (4)	C17—C18—C19—C20	−0.1 (4)
C9—C8—C11—C12	173.2 (3)	C8—C9—C10—C5	−0.2 (4)
C7—C8—C11—N1	167.1 (2)	C4—C5—C10—C9	−176.9 (3)
C9—C8—C11—N1	−10.0 (3)	C6—C5—C10—C9	2.3 (4)
C9—C8—C7—C6	2.6 (4)	O1—C18—C17—C16	178.6 (2)
C11—C8—C7—C6	−174.5 (2)	C19—C18—C17—C16	−1.0 (4)
C5—C6—C7—C8	−0.5 (4)	C13—N2—C14—C15	−174.3 (2)
C1—C6—C7—C8	176.9 (2)	C16—C15—C14—N2	177.6 (3)
C16—C15—C20—C19	−0.6 (4)	C20—C15—C14—N2	1.9 (4)
C14—C15—C20—C19	175.3 (2)	C20—C15—C16—C17	−0.5 (4)
C21—O1—C18—C17	8.3 (4)	C14—C15—C16—C17	−176.4 (2)
C21—O1—C18—C19	−172.1 (2)	C18—C17—C16—C15	1.3 (4)
C11—N1—C13—N2	174.8 (2)	C7—C6—C1—C2	−176.4 (3)
C11—N1—C13—S1	−0.4 (3)	C5—C6—C1—C2	1.1 (4)
C14—N2—C13—N1	7.1 (4)	N1—C11—C12—S1	−0.9 (3)
C14—N2—C13—S1	−177.7 (2)	C8—C11—C12—S1	176.1 (2)
C12—S1—C13—N1	0.0 (2)	C13—S1—C12—C11	0.5 (2)
C12—S1—C13—N2	−175.9 (2)	C6—C1—C2—C3	−1.1 (4)
C7—C6—C5—C4	177.3 (2)	C18—O1—C21—C22	174.3 (2)
C1—C6—C5—C4	−0.3 (4)	C10—C5—C4—C3	178.6 (3)
C7—C6—C5—C10	−1.9 (4)	C6—C5—C4—C3	−0.5 (4)
C1—C6—C5—C10	−179.5 (2)	C5—C4—C3—C2	0.6 (5)
C7—C8—C9—C10	−2.3 (4)	C1—C2—C3—C4	0.3 (5)
C11—C8—C9—C10	174.9 (2)	O1—C21—C22—C23	−61.0 (3)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg3^i	0.93	2.83	3.496	130
C16—H16···Cg3^ii	0.93	3.00	3.607	125

Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x, −y+1/2, z+1/2.