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In the mol­ecule of the title compound, C21H18N4O2S, all of the rings are individually planar. In the crystal structure, the mol­ecules are linked by inter­molecular N—H...O hydrogen bonds, forming an infinite chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603128X/ym2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603128X/ym2023Isup2.hkl
Contains datablock I

CCDC reference: 621561

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.078
  • wR factor = 0.162
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl [2-(2-phenyl-1H-indol-3-yldiazenyl)-1,3-thiazol-4-yl]acetate top
Crystal data top
C21H18N4O2SF(000) = 816
Mr = 390.45Dx = 1.364 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8200 reflections
a = 10.6111 (1) Åθ = 2.1–30.5°
b = 10.5040 (2) ŵ = 0.20 mm1
c = 17.3345 (2) ÅT = 294 K
β = 100.248 (1)°Block, brown
V = 1901.26 (5) Å30.35 × 0.25 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
5786 independent reflections
Radiation source: fine-focus sealed tube3501 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ω scansθmax = 30.5°, θmin = 2.4°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1515
Tmin = 0.935, Tmax = 0.971k = 1114
36040 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162All H-atom parameters refined
S = 1.11 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.4823P]
where P = (Fo2 + 2Fc2)/3
5786 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Å2) top
xyzUiso*/Ueq
S10.43322 (6)0.45119 (7)0.18283 (4)0.0661 (2)
O10.73623 (19)0.4843 (2)0.42446 (12)0.0901 (7)
O20.88710 (15)0.62048 (17)0.40486 (10)0.0635 (5)
N0.40102 (17)0.71137 (19)0.18711 (11)0.0540 (5)
N'0.28557 (17)0.67645 (19)0.15895 (10)0.0506 (5)
N10.01480 (19)0.8701 (2)0.09666 (12)0.0570 (5)
N30.59946 (16)0.61959 (19)0.24134 (11)0.0542 (5)
C20.4812 (2)0.6065 (2)0.20544 (13)0.0485 (5)
C40.6573 (2)0.5024 (2)0.25295 (14)0.0537 (6)
C50.5838 (2)0.4026 (3)0.22541 (17)0.0649 (7)
C60.7930 (2)0.4974 (3)0.29648 (17)0.0630 (7)
C70.8008 (2)0.5315 (3)0.38129 (16)0.0621 (7)
C80.9049 (3)0.6572 (3)0.48832 (17)0.0729 (8)
C91.0081 (4)0.7528 (5)0.5024 (2)0.0982 (12)
C100.2016 (2)0.7747 (2)0.13902 (13)0.0496 (5)
C110.2242 (2)0.9103 (2)0.13926 (13)0.0503 (5)
C120.3313 (2)0.9894 (3)0.15871 (15)0.0569 (6)
C130.3143 (3)1.1185 (3)0.15185 (17)0.0668 (7)
C140.1949 (3)1.1728 (3)0.12612 (17)0.0687 (7)
C150.0875 (3)1.0974 (3)0.10529 (16)0.0643 (7)
C160.1048 (2)0.9668 (2)0.11197 (14)0.0528 (6)
C170.0703 (2)0.7543 (2)0.11305 (13)0.0513 (5)
C180.0072 (2)0.6374 (2)0.10495 (14)0.0547 (6)
C190.1262 (3)0.6345 (4)0.0580 (2)0.0941 (11)
C200.2000 (4)0.5259 (4)0.0525 (3)0.1160 (15)
C210.1578 (3)0.4194 (4)0.0938 (2)0.0887 (10)
C220.0405 (3)0.4194 (3)0.14095 (19)0.0699 (7)
C230.0355 (2)0.5275 (3)0.14619 (16)0.0608 (6)
H10.072 (2)0.882 (2)0.0820 (14)0.067 (8)*
H50.607 (3)0.320 (3)0.2296 (16)0.086 (9)*
H120.414 (2)0.948 (2)0.1802 (14)0.071 (8)*
H130.389 (3)1.169 (3)0.1670 (16)0.087 (9)*
H140.186 (3)1.264 (3)0.1218 (17)0.096 (10)*
H150.001 (2)1.133 (2)0.0839 (14)0.068 (7)*
H190.154 (3)0.709 (3)0.0262 (19)0.108 (11)*
H200.280 (4)0.530 (4)0.016 (2)0.140 (14)*
H210.212 (3)0.353 (3)0.0916 (16)0.084 (9)*
H220.012 (3)0.343 (3)0.1724 (18)0.108 (11)*
H230.122 (3)0.527 (3)0.1844 (15)0.076 (8)*
H610.822 (3)0.410 (3)0.2936 (16)0.087 (9)*
H620.853 (3)0.551 (3)0.2724 (16)0.078 (9)*
H810.818 (3)0.691 (3)0.4973 (15)0.082 (9)*
H820.919 (3)0.574 (3)0.5208 (18)0.094 (10)*
H911.093 (4)0.723 (4)0.486 (2)0.132 (14)*
H921.025 (3)0.775 (3)0.556 (2)0.109 (12)*
H930.976 (4)0.836 (5)0.469 (2)0.151 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0545 (4)0.0512 (4)0.0853 (5)0.0006 (3)0.0070 (3)0.0105 (3)
O10.0663 (12)0.1207 (19)0.0805 (14)0.0330 (12)0.0052 (10)0.0157 (12)
O20.0541 (10)0.0732 (12)0.0629 (11)0.0076 (9)0.0096 (8)0.0004 (9)
N0.0434 (10)0.0509 (12)0.0660 (12)0.0038 (8)0.0049 (8)0.0023 (9)
N'0.0433 (10)0.0531 (12)0.0548 (11)0.0046 (8)0.0070 (8)0.0006 (9)
N10.0447 (11)0.0555 (13)0.0686 (13)0.0079 (9)0.0042 (9)0.0068 (10)
N30.0402 (10)0.0534 (13)0.0671 (13)0.0001 (8)0.0044 (8)0.0065 (9)
C20.0463 (12)0.0442 (13)0.0549 (13)0.0007 (10)0.0087 (9)0.0049 (10)
C40.0425 (12)0.0543 (15)0.0624 (15)0.0069 (10)0.0044 (10)0.0038 (11)
C50.0569 (15)0.0498 (17)0.0831 (19)0.0091 (12)0.0010 (12)0.0056 (13)
C60.0413 (13)0.0686 (19)0.0770 (18)0.0102 (12)0.0046 (11)0.0050 (14)
C70.0378 (12)0.0697 (18)0.0748 (17)0.0032 (11)0.0008 (11)0.0078 (14)
C80.0671 (18)0.088 (2)0.0634 (18)0.0019 (16)0.0118 (13)0.0041 (16)
C90.100 (3)0.120 (4)0.075 (2)0.027 (2)0.017 (2)0.026 (2)
C100.0447 (12)0.0500 (14)0.0541 (13)0.0030 (10)0.0087 (9)0.0010 (10)
C110.0470 (12)0.0533 (15)0.0518 (13)0.0052 (10)0.0120 (9)0.0015 (10)
C120.0490 (13)0.0556 (16)0.0667 (16)0.0013 (11)0.0119 (11)0.0039 (12)
C130.0625 (17)0.0575 (18)0.0826 (19)0.0046 (13)0.0188 (14)0.0060 (14)
C140.0763 (19)0.0498 (17)0.0826 (19)0.0046 (14)0.0209 (14)0.0048 (14)
C150.0632 (17)0.0565 (17)0.0736 (18)0.0153 (13)0.0132 (13)0.0089 (13)
C160.0491 (13)0.0529 (15)0.0572 (14)0.0043 (10)0.0118 (10)0.0033 (11)
C170.0457 (12)0.0535 (14)0.0543 (13)0.0065 (10)0.0081 (10)0.0033 (11)
C180.0449 (12)0.0601 (16)0.0580 (14)0.0003 (11)0.0062 (10)0.0005 (11)
C190.0664 (19)0.079 (2)0.121 (3)0.0127 (16)0.0264 (18)0.027 (2)
C200.080 (2)0.101 (3)0.145 (4)0.027 (2)0.039 (2)0.026 (3)
C210.070 (2)0.071 (2)0.120 (3)0.0223 (17)0.0044 (18)0.0050 (19)
C220.0641 (17)0.0587 (18)0.088 (2)0.0013 (13)0.0166 (14)0.0011 (15)
C230.0513 (14)0.0556 (16)0.0746 (17)0.0033 (11)0.0083 (12)0.0024 (12)
Geometric parameters (Å, º) top
S1—C51.714 (3)C10—C111.444 (3)
S1—C21.733 (2)C11—C121.400 (3)
N—C21.394 (3)C11—C161.403 (3)
N'—N1.289 (2)C12—H121.00 (3)
N'—C101.367 (3)C13—C121.371 (4)
N1—C171.360 (3)C13—C141.388 (4)
N1—H10.92 (2)C13—H130.95 (3)
N3—C21.305 (3)C14—C151.382 (4)
N3—C41.374 (3)C14—H140.96 (3)
O2—C71.322 (3)C15—H151.00 (2)
O2—C81.477 (3)C16—C151.386 (4)
C4—C51.341 (4)C16—N11.387 (3)
C4—C61.504 (3)C17—C181.470 (3)
C5—H50.91 (3)C18—C191.375 (3)
C6—H621.00 (3)C18—C231.391 (3)
C6—H610.97 (3)C19—C201.377 (5)
C7—O11.207 (3)C19—H190.97 (3)
C7—C61.501 (4)C20—H200.96 (4)
C8—C91.474 (5)C21—C201.361 (5)
C8—H811.03 (3)C21—H210.90 (3)
C8—H821.04 (3)C22—C211.363 (4)
C9—H911.04 (4)C22—H220.99 (3)
C9—H920.95 (4)C23—C221.386 (4)
C9—H931.07 (5)C23—H231.03 (3)
C10—C171.402 (3)
C5—S1—C288.19 (13)C17—C10—C11107.9 (2)
C7—O2—C8116.7 (2)C12—C11—C16118.4 (2)
N'—N—C2111.23 (19)C12—C11—C10135.5 (2)
N—N'—C10114.4 (2)C16—C11—C10106.1 (2)
C17—N1—C16110.93 (19)C13—C12—C11118.5 (2)
C17—N1—H1123.7 (16)C13—C12—H12124.2 (15)
C16—N1—H1125.1 (16)C11—C12—H12117.1 (15)
C2—N3—C4109.96 (19)C12—C13—C14122.2 (3)
N3—C2—N121.4 (2)C12—C13—H13116.1 (19)
N3—C2—S1115.24 (17)C14—C13—H13121.7 (19)
N—C2—S1123.32 (16)C15—C14—C13120.8 (3)
C5—C4—N3115.6 (2)C15—C14—H14119.0 (18)
C5—C4—C6126.6 (2)C13—C14—H14120.2 (18)
N3—C4—C6117.8 (2)C14—C15—C16117.0 (3)
C4—C5—S1111.0 (2)C14—C15—H15123.1 (15)
C4—C5—H5126.3 (18)C16—C15—H15119.8 (15)
S1—C5—H5122.6 (18)C15—C16—N1129.2 (2)
C7—C6—C4111.3 (2)C15—C16—C11123.1 (2)
C7—C6—H62110.3 (16)N1—C16—C11107.7 (2)
C4—C6—H62113.1 (16)N1—C17—C10107.4 (2)
C7—C6—H61108.2 (17)N1—C17—C18120.8 (2)
C4—C6—H61106.8 (17)C10—C17—C18131.7 (2)
H62—C6—H61107 (2)C19—C18—C23117.8 (3)
O1—C7—O2122.5 (3)C19—C18—C17121.0 (2)
O1—C7—C6124.8 (3)C23—C18—C17121.2 (2)
O2—C7—C6112.7 (2)C18—C19—C20120.7 (3)
C9—C8—O2107.6 (3)C18—C19—H19118.2 (19)
C9—C8—H81113.9 (16)C20—C19—H19120.9 (19)
O2—C8—H81106.0 (15)C21—C20—C19121.0 (3)
C9—C8—H82117.0 (17)C21—C20—H20123 (2)
O2—C8—H82107.0 (17)C19—C20—H20116 (2)
H81—C8—H82105 (2)C20—C21—C22119.7 (3)
C8—C9—H91114 (2)C20—C21—H21118.0 (19)
C8—C9—H92110 (2)C22—C21—H21122.2 (19)
H91—C9—H92109 (3)C21—C22—C23119.9 (3)
C8—C9—H93108 (2)C21—C22—H22119.4 (19)
H91—C9—H93108 (3)C23—C22—H22120.6 (19)
H92—C9—H93109 (3)C22—C23—C18120.9 (2)
N'—C10—C17122.1 (2)C22—C23—H23118.4 (15)
N'—C10—C11130.0 (2)C18—C23—H23120.5 (15)
C5—S1—C2—N30.2 (2)C11—C10—C17—N11.1 (3)
C5—S1—C2—N179.9 (2)C17—C10—C11—C12179.7 (3)
C2—S1—C5—C40.2 (2)C17—C10—C11—C160.9 (3)
C7—O2—C8—C9177.8 (3)C12—C11—C16—C151.7 (4)
C8—O2—C7—O12.1 (4)C10—C11—C16—C15178.8 (2)
C8—O2—C7—C6177.9 (2)C12—C11—C16—N1179.9 (2)
N'—N—C2—N3173.6 (2)C10—C11—C16—N10.4 (3)
N'—N—C2—S16.4 (3)C16—C11—C12—C131.4 (4)
C10—N'—N—C2179.50 (18)C10—C11—C12—C13179.3 (3)
N—N'—C10—C17175.1 (2)C14—C13—C12—C110.2 (4)
N—N'—C10—C115.1 (3)C12—C13—C14—C150.8 (5)
C16—N1—C17—C100.8 (3)C13—C14—C15—C160.5 (4)
C16—N1—C17—C18177.1 (2)N1—C16—C15—C14178.8 (2)
C2—N3—C4—C50.7 (3)C11—C16—C15—C140.7 (4)
C2—N3—C4—C6177.7 (2)C15—C16—N1—C17178.0 (3)
C4—N3—C2—N179.5 (2)C11—C16—N1—C170.2 (3)
C4—N3—C2—S10.5 (3)N1—C17—C18—C1921.4 (4)
C5—C4—C6—C7109.1 (3)C10—C17—C18—C19161.2 (3)
N3—C4—C6—C769.0 (3)N1—C17—C18—C23156.6 (2)
N3—C4—C5—S10.5 (3)C10—C17—C18—C2320.7 (4)
C6—C4—C5—S1177.7 (2)C19—C18—C23—C221.0 (4)
O1—C7—C6—C451.0 (4)C17—C18—C23—C22177.1 (2)
O2—C7—C6—C4128.9 (2)C23—C18—C19—C200.1 (5)
N'—C10—C17—N1178.7 (2)C17—C18—C19—C20178.1 (4)
N'—C10—C11—C120.5 (5)C18—C19—C20—C210.6 (7)
N'—C10—C11—C16178.9 (2)C22—C21—C20—C190.5 (7)
N'—C10—C17—C183.7 (4)C23—C22—C21—C200.5 (6)
C11—C10—C17—C18176.5 (2)C18—C23—C22—C211.2 (5)
 

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