Crystal structure and Hirshfeld surface analysis of 4-{[(E)-4-(hept­yloxy)benzyl­idene]amino}-N-(naphthalen-2-yl)-1,3-thia­zol-2-amine

Charge-assisted C—H...π hydrogen bonds along with π–π inter­actions stabilize the crystalline state. Inter­molecular inter­actions are qu­anti­fied by Hirshfeld surface analysis.

checkCIF/PLATON results

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Datablock: I


Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        49% Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1       --C13      .        5.5 s.u.
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        S1      0.105 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00538 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     37.394 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.174 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.334 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.749 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596         25 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.7 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
  10 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 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-RED32 (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-{[(E)-4-(Heptyloxy)benzylidene]amino}-N-(naphthalen-2-yl)-1,3-thiazol-2-amine

Crystal data

C27H28N2OS	F(000) = 912
Mr = 428.57	Dx = 1.229 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.927 (4) Å	Cell parameters from 9222 reflections
b = 5.9315 (6) Å	θ = 1.4–27.7°
c = 17.191 (2) Å	µ = 0.16 mm^−1
β = 97.734 (12)°	T = 296 K
V = 2316.6 (5) Å^3	Stick, yellow
Z = 4	0.49 × 0.24 × 0.11 mm

Data collection

Stoe IPDS 2 diffractometer	4068 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2000 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.063
Detector resolution: 6.67 pixels mm^-1	θmax = 25.1°, θmin = 2.4°
rotation method scans	h = −24→27
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
Tmin = 0.955, Tmax = 0.982	l = −20→20
10986 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0697P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
4068 reflections	Δρmax = 0.23 e Å^−3
281 parameters	Δρmin = −0.17 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	0.22633 (5)	0.01514 (16)	0.57256 (6)	0.1138 (4)
O1	0.34973 (11)	0.7781 (4)	0.18878 (14)	0.1090 (7)
N1	0.17508 (13)	0.3977 (5)	0.56495 (16)	0.0951 (8)
N2	0.23575 (14)	0.3219 (5)	0.46375 (17)	0.1016 (8)
C6	0.09218 (14)	0.4575 (5)	0.81098 (19)	0.0907 (9)
C7	0.12144 (15)	0.3353 (5)	0.7578 (2)	0.0922 (9)
H7	0.138236	0.197033	0.773380	0.111*
C18	0.31570 (16)	0.7233 (6)	0.24384 (19)	0.0942 (9)
C8	0.12605 (15)	0.4127 (5)	0.68404 (19)	0.0893 (9)
C13	0.20898 (16)	0.2713 (6)	0.52869 (19)	0.0957 (9)
C15	0.25439 (16)	0.5758 (6)	0.36278 (18)	0.0911 (9)
C9	0.09865 (16)	0.6188 (6)	0.6604 (2)	0.0983 (10)
H9	0.100324	0.671600	0.609769	0.118*
C16	0.29941 (17)	0.4482 (6)	0.33942 (19)	0.1012 (10)
H16	0.309049	0.310612	0.363781	0.121*
C5	0.06665 (15)	0.6676 (6)	0.7867 (2)	0.0957 (9)
C19	0.27062 (16)	0.8513 (6)	0.2650 (2)	0.0987 (10)
H19	0.260471	0.986613	0.239358	0.118*
C11	0.16110 (15)	0.2922 (5)	0.63110 (19)	0.0905 (9)
C17	0.32949 (17)	0.5193 (6)	0.28215 (19)	0.1011 (10)
H17	0.359909	0.431246	0.267905	0.121*
C20	0.24043 (16)	0.7789 (6)	0.3243 (2)	0.1000 (10)
H20	0.210185	0.867189	0.338883	0.120*
C10	0.07004 (16)	0.7411 (6)	0.7095 (2)	0.1021 (10)
H10	0.052252	0.876263	0.692155	0.123*
C1	0.08963 (16)	0.3841 (7)	0.8886 (2)	0.1035 (10)
H1	0.105644	0.245213	0.905032	0.124*
C14	0.22370 (16)	0.5061 (6)	0.42680 (19)	0.0977 (9)
H14	0.194260	0.598284	0.441516	0.117*
C12	0.18554 (17)	0.0833 (6)	0.6429 (2)	0.1043 (10)
H12	0.180195	−0.009921	0.684812	0.125*
C4	0.04009 (17)	0.7950 (7)	0.8408 (2)	0.1113 (11)
H4	0.023035	0.933143	0.825662	0.134*
C23	0.37841 (18)	0.7782 (7)	0.0293 (2)	0.1100 (11)
H23A	0.385642	0.645391	0.062131	0.132*
H23B	0.340038	0.760901	−0.001570	0.132*
C21	0.33361 (18)	0.9678 (6)	0.1388 (2)	0.1106 (11)
H21A	0.334233	1.104756	0.169733	0.133*
H21B	0.294231	0.947554	0.111073	0.133*
C25	0.42596 (19)	0.5902 (7)	−0.0784 (2)	0.1155 (12)
H25A	0.432021	0.455243	−0.046493	0.139*
H25B	0.388034	0.576225	−0.110681	0.139*
C24	0.42408 (18)	0.7903 (7)	−0.0250 (2)	0.1128 (11)
H24A	0.462375	0.806563	0.006187	0.135*
H24B	0.417052	0.924663	−0.057046	0.135*
C2	0.06433 (18)	0.5126 (8)	0.9391 (2)	0.1156 (11)
H2	0.063744	0.463555	0.990321	0.139*
C22	0.37726 (19)	0.9836 (7)	0.0817 (2)	0.1149 (11)
H22A	0.416186	1.005154	0.110597	0.138*
H22B	0.368155	1.115365	0.048834	0.138*
C26	0.4728 (2)	0.6016 (8)	−0.1311 (2)	0.1277 (14)
H26A	0.510749	0.615254	−0.098731	0.153*
H26B	0.466844	0.736962	−0.162780	0.153*
C3	0.0389 (2)	0.7194 (8)	0.9150 (3)	0.1247 (13)
H3	0.021019	0.806070	0.950183	0.150*
C27	0.4750 (2)	0.4030 (8)	−0.1848 (3)	0.1497 (17)
H27A	0.438855	0.394620	−0.220161	0.225*
H27B	0.480019	0.267150	−0.154273	0.225*
H27C	0.507361	0.420161	−0.214350	0.225*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1338 (8)	0.0960 (6)	0.1147 (7)	0.0124 (6)	0.0282 (6)	0.0065 (5)
O1	0.1105 (17)	0.1179 (17)	0.1008 (15)	0.0099 (14)	0.0219 (14)	0.0124 (14)
N1	0.101 (2)	0.0915 (16)	0.0922 (17)	0.0001 (15)	0.0123 (15)	0.0032 (15)
N2	0.117 (2)	0.0974 (19)	0.0913 (17)	−0.0022 (17)	0.0169 (16)	0.0002 (16)
C6	0.085 (2)	0.091 (2)	0.094 (2)	−0.0032 (17)	0.0068 (17)	−0.0021 (18)
C7	0.095 (2)	0.0804 (19)	0.099 (2)	−0.0006 (17)	0.0065 (19)	0.0057 (17)
C18	0.096 (2)	0.102 (2)	0.0839 (19)	0.000 (2)	0.0095 (18)	−0.0011 (19)
C8	0.088 (2)	0.0826 (19)	0.097 (2)	−0.0055 (16)	0.0109 (18)	0.0054 (17)
C13	0.096 (2)	0.101 (2)	0.089 (2)	−0.0075 (19)	0.0092 (19)	−0.0060 (19)
C15	0.096 (2)	0.091 (2)	0.0856 (19)	0.0002 (18)	0.0093 (17)	−0.0069 (17)
C9	0.098 (2)	0.093 (2)	0.103 (2)	−0.0053 (19)	0.012 (2)	0.0107 (19)
C16	0.121 (3)	0.090 (2)	0.092 (2)	0.009 (2)	0.013 (2)	0.0028 (18)
C5	0.087 (2)	0.091 (2)	0.109 (3)	−0.0041 (18)	0.0102 (19)	−0.0008 (19)
C19	0.104 (3)	0.094 (2)	0.098 (2)	0.007 (2)	0.014 (2)	0.0085 (18)
C11	0.093 (2)	0.085 (2)	0.092 (2)	−0.0088 (18)	0.0082 (18)	0.0037 (17)
C17	0.113 (3)	0.097 (2)	0.095 (2)	0.016 (2)	0.018 (2)	−0.001 (2)
C20	0.101 (2)	0.096 (2)	0.102 (2)	0.0135 (19)	0.014 (2)	−0.003 (2)
C10	0.100 (2)	0.085 (2)	0.120 (3)	0.0019 (18)	0.015 (2)	0.010 (2)
C1	0.103 (3)	0.110 (2)	0.098 (2)	0.005 (2)	0.014 (2)	0.005 (2)
C14	0.103 (2)	0.096 (2)	0.093 (2)	−0.002 (2)	0.0103 (19)	−0.005 (2)
C12	0.116 (3)	0.091 (2)	0.106 (2)	0.001 (2)	0.012 (2)	0.0129 (18)
C4	0.110 (3)	0.103 (2)	0.121 (3)	0.006 (2)	0.015 (2)	−0.005 (2)
C23	0.109 (3)	0.117 (3)	0.104 (2)	−0.009 (2)	0.014 (2)	0.011 (2)
C21	0.122 (3)	0.102 (2)	0.107 (2)	−0.001 (2)	0.015 (2)	0.008 (2)
C25	0.120 (3)	0.126 (3)	0.100 (2)	−0.006 (2)	0.015 (2)	0.009 (2)
C24	0.113 (3)	0.126 (3)	0.100 (2)	−0.011 (2)	0.017 (2)	0.015 (2)
C2	0.112 (3)	0.133 (3)	0.101 (2)	0.008 (3)	0.013 (2)	0.001 (3)
C22	0.121 (3)	0.114 (3)	0.112 (2)	−0.010 (2)	0.023 (2)	0.015 (2)
C26	0.137 (4)	0.142 (3)	0.107 (3)	−0.009 (3)	0.026 (3)	0.003 (3)
C3	0.128 (3)	0.128 (3)	0.122 (3)	0.013 (3)	0.030 (3)	−0.017 (3)
C27	0.173 (5)	0.157 (4)	0.121 (3)	0.002 (3)	0.029 (3)	−0.014 (3)

Geometric parameters (Å, º)

S1—C12	1.674 (4)	C10—H10	0.9300
S1—C13	1.719 (4)	C1—C2	1.343 (5)
O1—C18	1.345 (4)	C1—H1	0.9300
O1—C21	1.434 (4)	C14—H14	0.9300
N1—C13	1.298 (4)	C12—H12	0.9300
N1—C11	1.373 (4)	C4—C3	1.356 (5)
N2—C14	1.275 (4)	C4—H4	0.9300
N2—C13	1.377 (4)	C23—C24	1.495 (5)
C6—C7	1.406 (4)	C23—C22	1.517 (5)
C6—C1	1.413 (4)	C23—H23A	0.9700
C6—C5	1.416 (5)	C23—H23B	0.9700
C7—C8	1.366 (4)	C21—C22	1.497 (5)
C7—H7	0.9300	C21—H21A	0.9700
C18—C19	1.370 (5)	C21—H21B	0.9700
C18—C17	1.394 (5)	C25—C26	1.497 (5)
C8—C9	1.409 (5)	C25—C24	1.505 (5)
C8—C11	1.477 (4)	C25—H25A	0.9700
C15—C16	1.382 (5)	C25—H25B	0.9700
C15—C20	1.391 (5)	C24—H24A	0.9700
C15—C14	1.444 (5)	C24—H24B	0.9700
C9—C10	1.349 (4)	C2—C3	1.397 (6)
C9—H9	0.9300	C2—H2	0.9300
C16—C17	1.344 (5)	C22—H22A	0.9700
C16—H16	0.9300	C22—H22B	0.9700
C5—C4	1.400 (5)	C26—C27	1.502 (6)
C5—C10	1.409 (5)	C26—H26A	0.9700
C19—C20	1.376 (4)	C26—H26B	0.9700
C19—H19	0.9300	C3—H3	0.9300
C11—C12	1.364 (5)	C27—H27A	0.9600
C17—H17	0.9300	C27—H27B	0.9600
C20—H20	0.9300	C27—H27C	0.9600
C12—S1—C13	89.11 (18)	C11—C12—H12	124.1
C18—O1—C21	119.0 (3)	S1—C12—H12	124.1
C13—N1—C11	110.8 (3)	C3—C4—C5	120.8 (4)
C14—N2—C13	120.0 (3)	C3—C4—H4	119.6
C7—C6—C1	122.7 (3)	C5—C4—H4	119.6
C7—C6—C5	118.5 (3)	C24—C23—C22	113.7 (3)
C1—C6—C5	118.8 (3)	C24—C23—H23A	108.8
C8—C7—C6	122.3 (3)	C22—C23—H23A	108.8
C8—C7—H7	118.9	C24—C23—H23B	108.8
C6—C7—H7	118.9	C22—C23—H23B	108.8
O1—C18—C19	125.6 (3)	H23A—C23—H23B	107.7
O1—C18—C17	115.2 (3)	O1—C21—C22	107.5 (3)
C19—C18—C17	119.1 (3)	O1—C21—H21A	110.2
C7—C8—C9	118.2 (3)	C22—C21—H21A	110.2
C7—C8—C11	121.7 (3)	O1—C21—H21B	110.2
C9—C8—C11	120.0 (3)	C22—C21—H21B	110.2
N1—C13—N2	128.6 (3)	H21A—C21—H21B	108.5
N1—C13—S1	114.7 (2)	C26—C25—C24	114.6 (3)
N2—C13—S1	116.5 (3)	C26—C25—H25A	108.6
C16—C15—C20	118.0 (3)	C24—C25—H25A	108.6
C16—C15—C14	121.6 (3)	C26—C25—H25B	108.6
C20—C15—C14	120.4 (3)	C24—C25—H25B	108.6
C10—C9—C8	121.4 (3)	H25A—C25—H25B	107.6
C10—C9—H9	119.3	C23—C24—C25	115.0 (3)
C8—C9—H9	119.3	C23—C24—H24A	108.5
C17—C16—C15	121.2 (3)	C25—C24—H24A	108.5
C17—C16—H16	119.4	C23—C24—H24B	108.5
C15—C16—H16	119.4	C25—C24—H24B	108.5
C4—C5—C10	122.9 (3)	H24A—C24—H24B	107.5
C4—C5—C6	118.6 (3)	C1—C2—C3	120.4 (4)
C10—C5—C6	118.5 (3)	C1—C2—H2	119.8
C18—C19—C20	119.7 (3)	C3—C2—H2	119.8
C18—C19—H19	120.1	C21—C22—C23	113.9 (3)
C20—C19—H19	120.1	C21—C22—H22A	108.8
C12—C11—N1	113.6 (3)	C23—C22—H22A	108.8
C12—C11—C8	126.5 (3)	C21—C22—H22B	108.8
N1—C11—C8	119.8 (3)	C23—C22—H22B	108.8
C16—C17—C18	120.8 (3)	H22A—C22—H22B	107.7
C16—C17—H17	119.6	C25—C26—C27	115.0 (4)
C18—C17—H17	119.6	C25—C26—H26A	108.5
C19—C20—C15	121.1 (3)	C27—C26—H26A	108.5
C19—C20—H20	119.5	C25—C26—H26B	108.5
C15—C20—H20	119.5	C27—C26—H26B	108.5
C9—C10—C5	121.1 (3)	H26A—C26—H26B	107.5
C9—C10—H10	119.5	C4—C3—C2	120.6 (4)
C5—C10—H10	119.5	C4—C3—H3	119.7
C2—C1—C6	120.7 (4)	C2—C3—H3	119.7
C2—C1—H1	119.6	C26—C27—H27A	109.5
C6—C1—H1	119.6	C26—C27—H27B	109.5
N2—C14—C15	122.0 (3)	H27A—C27—H27B	109.5
N2—C14—H14	119.0	C26—C27—H27C	109.5
C15—C14—H14	119.0	H27A—C27—H27C	109.5
C11—C12—S1	111.8 (3)	H27B—C27—H27C	109.5
C1—C6—C7—C8	−176.9 (3)	C15—C16—C17—C18	−0.8 (5)
C5—C6—C7—C8	0.1 (5)	O1—C18—C17—C16	178.7 (3)
C21—O1—C18—C19	−9.9 (5)	C19—C18—C17—C16	−0.3 (5)
C21—O1—C18—C17	171.2 (3)	C18—C19—C20—C15	−0.8 (5)
C6—C7—C8—C9	−2.1 (5)	C16—C15—C20—C19	−0.3 (5)
C6—C7—C8—C11	174.8 (3)	C14—C15—C20—C19	177.8 (3)
C11—N1—C13—N2	−175.0 (3)	C8—C9—C10—C5	0.2 (5)
C11—N1—C13—S1	−0.1 (4)	C4—C5—C10—C9	176.6 (4)
C14—N2—C13—N1	−7.2 (6)	C6—C5—C10—C9	−2.3 (5)
C14—N2—C13—S1	178.0 (3)	C7—C6—C1—C2	175.9 (4)
C12—S1—C13—N1	0.2 (3)	C5—C6—C1—C2	−1.1 (5)
C12—S1—C13—N2	175.8 (3)	C13—N2—C14—C15	174.4 (3)
C7—C8—C9—C10	2.0 (5)	C16—C15—C14—N2	−1.4 (5)
C11—C8—C9—C10	−175.0 (3)	C20—C15—C14—N2	−179.4 (3)
C20—C15—C16—C17	1.0 (5)	N1—C11—C12—S1	0.2 (4)
C14—C15—C16—C17	−177.0 (3)	C8—C11—C12—S1	−175.5 (3)
C7—C6—C5—C4	−176.8 (3)	C13—S1—C12—C11	−0.2 (3)
C1—C6—C5—C4	0.3 (5)	C10—C5—C4—C3	−178.7 (4)
C7—C6—C5—C10	2.1 (5)	C6—C5—C4—C3	0.2 (5)
C1—C6—C5—C10	179.2 (3)	C18—O1—C21—C22	−177.7 (3)
O1—C18—C19—C20	−177.8 (3)	C22—C23—C24—C25	−179.3 (3)
C17—C18—C19—C20	1.1 (5)	C26—C25—C24—C23	−178.5 (3)
C13—N1—C11—C12	−0.1 (4)	C6—C1—C2—C3	1.4 (6)
C13—N1—C11—C8	176.0 (3)	O1—C21—C22—C23	61.1 (4)
C7—C8—C11—C12	9.5 (5)	C24—C23—C22—C21	−177.2 (3)
C9—C8—C11—C12	−173.7 (4)	C24—C25—C26—C27	−179.8 (4)
C7—C8—C11—N1	−166.1 (3)	C5—C4—C3—C2	0.1 (6)
C9—C8—C11—N1	10.8 (5)	C1—C2—C3—C4	−0.9 (6)

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	2.85	3.522 (4)	130

Symmetry code: (i) −x, y+1/2, −z+3/2.