Download citation
Download citation
link to html
In the title mol­ecule, C14H10BrN3OS, the indole moiety is twisted by 36.0 (2)° with respect to the disordered thienyl group and the nitro­gen-bound H atoms interact with the amide O atoms of symmetry-related mol­ecules, resulting in an N—H...O hydrogen-bonded layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006616/lh6375sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006616/lh6375Isup2.hkl
Contains datablock I

CCDC reference: 270476

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.053
  • wR factor = 0.151
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??) >H1
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          >H2
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          >H3
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H1'
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H2'
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H3'
Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

Alert level B PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.71
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.178 0.293 Tmin' and Tmax expected: 0.216 0.293 RR' = 0.824 Please check that your absorption correction is appropriate. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc.
6 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-Bromo-1H-indole-3-carbaldehyde 2-thienoylhydrazone top
Crystal data top
C14H10BrN3OSF(000) = 1392
Mr = 348.22Dx = 1.645 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4416 reflections
a = 7.3437 (4) Åθ = 2.3–27.1°
b = 17.944 (1) ŵ = 3.07 mm1
c = 21.340 (1) ÅT = 295 K
V = 2812.1 (3) Å3Block, yellow
Z = 80.48 × 0.42 × 0.40 mm
Data collection top
Bruker SMART area-detector
diffractometer
3073 independent reflections
Radiation source: medium-focus sealed tube2135 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 95
Tmin = 0.178, Tmax = 0.293k = 2222
15764 measured reflectionsl = 2527
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0609P)2 + 8.173P]
where P = (Fo2 + 2Fc2)/3
3073 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 1.55 e Å3
111 restraintsΔρmin = 1.62 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br11.02049 (8)0.81548 (3)0.30123 (4)0.0810 (3)
S11.0480 (3)0.63318 (13)0.45490 (7)0.0580 (6)0.81 (1)
S1'0.9553 (14)0.6308 (7)0.5862 (4)0.0580 (6)0.19
O10.6683 (4)0.53474 (19)0.55821 (12)0.0491 (8)
N10.6990 (5)0.5259 (2)0.45473 (13)0.0388 (8)
H1n0.61640.49190.45430.047*
N20.7699 (4)0.55013 (18)0.39804 (13)0.0333 (7)
N30.7845 (5)0.5284 (2)0.18365 (14)0.0440 (9)
H3n0.77700.51230.14580.053*
C11.1918 (9)0.6756 (4)0.5056 (3)0.060 (2)0.81 (1)
H11.29460.70170.49270.072*0.807 (5)
C21.1453 (9)0.6683 (4)0.5655 (3)0.060 (2)0.81 (1)
H21.20980.68780.59920.072*0.807 (5)
C30.9856 (11)0.6272 (6)0.5701 (3)0.062 (2)0.81 (1)
H30.93030.61740.60840.074*0.807 (5)
C1'1.108 (3)0.6922 (14)0.5562 (15)0.060 (2)0.19
H1'1.16790.72520.58280.072*0.193 (5)
C2'1.143 (4)0.6935 (18)0.4951 (14)0.060 (2)0.19
H2'1.22170.72440.47310.072*0.193 (5)
C3'1.031 (4)0.637 (2)0.4724 (12)0.062 (2)0.19
H3'1.03390.62300.43040.074*0.193 (5)
C40.9143 (6)0.6017 (2)0.51413 (16)0.0387 (9)
C50.7531 (6)0.5529 (2)0.50999 (16)0.0364 (9)
C60.7242 (5)0.5100 (2)0.35109 (16)0.0305 (8)
H60.66060.46590.35780.037*
C70.7690 (5)0.5317 (2)0.28810 (15)0.0284 (8)
C80.7362 (6)0.4893 (2)0.23557 (16)0.0371 (9)
H80.68840.44130.23560.045*
C90.8470 (5)0.5975 (3)0.20111 (17)0.0381 (9)
C100.9089 (6)0.6573 (3)0.1653 (2)0.0548 (13)
H100.91520.65400.12180.066*
C110.9597 (7)0.7208 (3)0.1956 (3)0.0586 (14)
H111.00040.76170.17270.070*
C120.9512 (6)0.7248 (2)0.2605 (2)0.0470 (11)
C130.8934 (5)0.6668 (2)0.29728 (19)0.0352 (8)
H130.88960.67080.34070.042*
C140.8406 (5)0.6016 (2)0.26676 (15)0.0293 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0537 (3)0.0305 (3)0.1588 (8)0.0001 (2)0.0249 (4)0.0018 (3)
S10.0552 (10)0.0886 (13)0.0303 (9)0.0328 (9)0.0080 (7)0.0111 (8)
S1'0.0552 (10)0.0886 (13)0.0303 (9)0.0328 (9)0.0080 (7)0.0111 (8)
O10.0520 (18)0.075 (2)0.0202 (13)0.0126 (17)0.0040 (12)0.0070 (13)
N10.044 (2)0.051 (2)0.0205 (15)0.0166 (17)0.0029 (14)0.0039 (14)
N20.0384 (18)0.0425 (18)0.0190 (14)0.0074 (15)0.0029 (13)0.0039 (13)
N30.040 (2)0.072 (3)0.0196 (15)0.0074 (19)0.0014 (14)0.0062 (16)
C10.044 (4)0.080 (4)0.054 (4)0.015 (3)0.003 (3)0.009 (3)
C20.048 (3)0.081 (4)0.050 (4)0.010 (3)0.003 (3)0.026 (3)
C30.063 (4)0.097 (5)0.026 (3)0.011 (3)0.009 (3)0.021 (3)
C1'0.044 (4)0.080 (4)0.054 (4)0.015 (3)0.003 (3)0.009 (3)
C2'0.048 (3)0.081 (4)0.050 (4)0.010 (3)0.003 (3)0.026 (3)
C3'0.063 (4)0.097 (5)0.026 (3)0.011 (3)0.009 (3)0.021 (3)
C40.038 (2)0.050 (2)0.0277 (19)0.0002 (19)0.0035 (17)0.0058 (17)
C50.040 (2)0.049 (2)0.0210 (17)0.0019 (18)0.0001 (16)0.0044 (16)
C60.0343 (19)0.0330 (18)0.0243 (17)0.0030 (16)0.0008 (15)0.0028 (15)
C70.0298 (18)0.0328 (18)0.0225 (16)0.0018 (15)0.0010 (14)0.0007 (14)
C80.036 (2)0.047 (2)0.0280 (19)0.0030 (18)0.0007 (17)0.0054 (17)
C90.0283 (19)0.059 (3)0.0268 (18)0.0110 (18)0.0023 (15)0.0078 (18)
C100.040 (2)0.084 (3)0.041 (2)0.017 (2)0.013 (2)0.033 (2)
C110.044 (2)0.059 (3)0.072 (3)0.013 (2)0.018 (2)0.040 (3)
C120.031 (2)0.035 (2)0.074 (3)0.0064 (17)0.011 (2)0.016 (2)
C130.0302 (19)0.0321 (19)0.043 (2)0.0045 (15)0.0054 (17)0.0055 (17)
C140.0256 (17)0.0395 (19)0.0228 (17)0.0063 (15)0.0041 (14)0.0064 (15)
Geometric parameters (Å, º) top
Br1—C121.914 (5)C1'—H1'0.9300
S1—C11.692 (7)C2'—C3'1.396 (14)
S1—C41.697 (4)C2'—H2'0.9300
S1'—C41.653 (7)C3'—C41.386 (13)
S1'—C1'1.698 (12)C3'—H3'0.9300
O1—C51.246 (4)C4—C51.475 (6)
N1—C51.336 (5)C6—C71.438 (5)
N1—N21.387 (4)C6—H60.9300
N1—H1n0.8600C7—C81.376 (5)
N2—C61.279 (5)C7—C141.434 (5)
N3—C81.358 (5)C8—H80.9300
N3—C91.374 (6)C9—C101.394 (6)
N3—H3n0.8600C9—C141.404 (5)
C1—C21.329 (8)C10—C111.362 (8)
C1—H10.9300C10—H100.9300
C2—C31.389 (10)C11—C121.388 (7)
C2—H20.9300C11—H110.9300
C3—C41.382 (8)C12—C131.371 (6)
C3—H30.9300C13—C141.394 (5)
C1'—C2'1.329 (12)C13—H130.9300
C1—S1—C492.0 (3)C5—C4—S1128.1 (3)
C4—S1'—C1'88.5 (13)O1—C5—N1119.0 (4)
C5—N1—N2123.0 (3)O1—C5—C4120.5 (3)
C5—N1—H1n118.5N1—C5—C4120.5 (3)
N2—N1—H1n118.5N2—C6—C7121.3 (3)
C6—N2—N1114.1 (3)N2—C6—H6119.3
C8—N3—C9109.4 (3)C7—C6—H6119.3
C8—N3—H3n125.3C8—C7—C14106.8 (3)
C9—N3—H3n125.3C8—C7—C6124.9 (4)
C2—C1—S1114.2 (6)C14—C7—C6128.2 (3)
C2—C1—H1122.9N3—C8—C7109.5 (4)
S1—C1—H1122.9N3—C8—H8125.2
C1—C2—C3109.7 (6)C7—C8—H8125.2
C1—C2—H2125.1N3—C9—C10130.9 (4)
C3—C2—H2125.1N3—C9—C14107.9 (3)
C4—C3—C2115.8 (6)C10—C9—C14121.2 (4)
C4—C3—H3122.1C11—C10—C9118.2 (4)
C2—C3—H3122.1C11—C10—H10120.9
C2'—C1'—S1'121 (3)C9—C10—H10120.9
C2'—C1'—H1'119.7C10—C11—C12120.3 (4)
S1'—C1'—H1'119.7C10—C11—H11119.8
C1'—C2'—C3'102 (3)C12—C11—H11119.8
C1'—C2'—H2'128.8C13—C12—C11123.1 (5)
C3'—C2'—H2'128.8C13—C12—Br1117.9 (4)
C4—C3'—C2'118 (2)C11—C12—Br1119.0 (3)
C4—C3'—H3'120.9C12—C13—C14117.1 (4)
C2'—C3'—H3'120.9C12—C13—H13121.4
C3—C4—C5123.5 (4)C14—C13—H13121.4
C3'—C4—C5136.6 (13)C13—C14—C9120.0 (4)
C3'—C4—S1'110.0 (14)C13—C14—C7133.4 (3)
C5—C4—S1'112.9 (4)C9—C14—C7106.5 (3)
C3—C4—S1108.3 (4)
C5—N1—N2—C6169.2 (4)C3—C4—C5—N1175.2 (6)
C4—S1—C1—C20.6 (6)C3'—C4—C5—N18 (3)
S1—C1—C2—C30.5 (8)S1'—C4—C5—N1178.6 (6)
C1—C2—C3—C41.7 (10)S1—C4—C5—N12.1 (6)
C4—S1'—C1'—C2'2.5 (14)N1—N2—C6—C7173.1 (3)
S1'—C1'—C2'—C3'0.6 (18)N2—C6—C7—C8175.2 (4)
C1'—C2'—C3'—C45 (3)N2—C6—C7—C1410.2 (6)
C2—C3—C4—C3'6.3 (19)C9—N3—C8—C70.9 (5)
C2—C3—C4—C5175.7 (6)C14—C7—C8—N30.5 (4)
C2—C3—C4—S1'155 (4)C6—C7—C8—N3176.1 (4)
C2—C3—C4—S12.1 (9)C8—N3—C9—C10178.9 (4)
C2'—C3'—C4—C313 (3)C8—N3—C9—C141.0 (4)
C2'—C3'—C4—C5164.5 (17)N3—C9—C10—C11178.6 (4)
C2'—C3'—C4—S1'7 (4)C14—C9—C10—C111.4 (6)
C2'—C3'—C4—S1168 (14)C9—C10—C11—C120.6 (7)
C1'—S1'—C4—C337 (4)C10—C11—C12—C130.3 (7)
C1'—S1'—C4—C3'5 (2)C10—C11—C12—Br1179.1 (3)
C1'—S1'—C4—C5168.7 (10)C11—C12—C13—C140.4 (6)
C1'—S1'—C4—S18.1 (11)Br1—C12—C13—C14179.0 (3)
C1—S1—C4—C31.4 (6)C12—C13—C14—C90.4 (5)
C1—S1—C4—C3'28 (11)C12—C13—C14—C7177.7 (4)
C1—S1—C4—C5176.2 (5)N3—C9—C14—C13178.7 (3)
C1—S1—C4—S1'7.6 (6)C10—C9—C14—C131.3 (6)
N2—N1—C5—O1171.6 (4)N3—C9—C14—C70.7 (4)
N2—N1—C5—C410.2 (6)C10—C9—C14—C7179.3 (4)
C3—C4—C5—O13.0 (8)C8—C7—C14—C13177.7 (4)
C3'—C4—C5—O1174 (3)C6—C7—C14—C132.3 (7)
S1'—C4—C5—O13.3 (7)C8—C7—C14—C90.1 (4)
S1—C4—C5—O1179.7 (4)C6—C7—C14—C9175.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.862.162.921 (5)147
N3—H3n···O1ii0.862.092.927 (4)165
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y+1, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds