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The crystal structure of the title compound, C17H15BrN2O2, has been determined at room temperature. The indole moiety is essentially planar and the structure is stabilized by intra- and intermolecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010176/cf6180sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010176/cf6180Isup2.hkl
Contains datablock I

CCDC reference: 189894

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.084
  • Data-to-parameter ratio = 16.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.43 From the CIF: _reflns_number_total 6698 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 7145 Completeness (_total/calc) 93.74% Alert C: < 95% complete PLAT_420 Alert C D-H Without Acceptor N(4) - H(4A) ? PLAT_725 Alert C D-H Calc 0.96991, Rep 0.98000, Dev. 0.01 Ang. C33 -H33B 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

Ethyl 5-bromo-3-phenyl indole-2-carbamate top
Crystal data top
C17H15BrN2O2F(000) = 1456
Mr = 359.21Dx = 1.524 Mg m3
Monoclinic, P21/nMelting point: 408 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 13.602 (2) ÅCell parameters from 9585 reflections
b = 10.1781 (17) Åθ = 2.2–23.3°
c = 23.565 (4) ŵ = 2.63 mm1
β = 106.267 (3)°T = 293 K
V = 3131.8 (9) Å3Prism, pale brown
Z = 80.32 × 0.21 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
6698 independent reflections
Radiation source: fine-focus sealed tube4047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
φ and ω scansθmax = 27.4°, θmin = 1.6°
Absorption correction: multi-scan
(XPREP; Bruker, 1998)
h = 1717
Tmin = 0.514, Tmax = 0.769k = 1313
39464 measured reflectionsl = 3028
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0456P)2]
where P = (Fo2 + 2Fc2)/3
6698 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.38 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
Br10.67662 (2)1.15732 (3)0.154547 (13)0.06427 (11)
O10.46579 (13)0.55345 (17)0.11174 (8)0.0547 (5)
O20.32817 (12)0.43617 (16)0.10689 (7)0.0514 (4)
C30.51756 (16)0.8510 (2)0.05363 (10)0.0402 (6)
C50.63207 (18)1.0224 (2)0.09692 (11)0.0444 (6)
C90.34687 (16)0.7463 (2)0.06361 (10)0.0395 (6)
N20.39265 (14)0.58025 (19)0.03663 (9)0.0458 (5)
H20.34800.54680.02130.055*
C150.40183 (18)0.5258 (2)0.08708 (11)0.0435 (6)
C20.43360 (16)0.7585 (2)0.03809 (10)0.0389 (6)
C40.54488 (17)0.9524 (2)0.09527 (11)0.0446 (6)
H40.50560.97160.12080.054*
C10.44969 (16)0.6863 (2)0.00733 (10)0.0408 (6)
N10.53542 (14)0.7262 (2)0.02121 (9)0.0451 (5)
H10.55870.69330.04850.054*
C80.57866 (16)0.8280 (2)0.01574 (10)0.0421 (6)
C70.66524 (18)0.9013 (3)0.01738 (11)0.0494 (6)
H70.70380.88510.00880.059*
C140.36170 (18)0.7435 (2)0.12431 (11)0.0472 (6)
H140.42760.75130.14950.057*
C60.69212 (18)0.9994 (3)0.05932 (11)0.0490 (6)
H60.75041.04980.06230.059*
C100.24711 (17)0.7351 (2)0.02745 (11)0.0461 (6)
H100.23500.73750.01340.055*
C130.2802 (2)0.7292 (3)0.14777 (12)0.0542 (7)
H130.29140.72830.18860.065*
C120.1827 (2)0.7164 (3)0.11124 (13)0.0553 (7)
H120.12810.70480.12720.066*
C110.16562 (18)0.7205 (3)0.05113 (12)0.0535 (7)
H110.09930.71350.02630.064*
C160.32765 (19)0.3715 (3)0.16147 (11)0.0559 (7)
H16A0.39370.33110.15790.067*
H16B0.31430.43480.19350.067*
C170.2461 (2)0.2695 (3)0.17407 (11)0.0600 (7)
H17A0.25940.20790.14200.090*
H17B0.24550.22420.20990.090*
H17C0.18090.31050.17850.090*
Br20.00498 (2)1.05496 (4)0.075163 (13)0.07498 (13)
O30.21149 (13)0.90039 (19)0.45332 (7)0.0588 (5)
N30.13685 (14)0.9018 (2)0.32998 (8)0.0474 (5)
H30.10670.88470.35670.057*
O40.37786 (12)0.8434 (2)0.48626 (7)0.0654 (5)
N40.30944 (14)0.8667 (2)0.39108 (9)0.0511 (6)
H4A0.36930.84100.39020.061*
C180.24032 (17)0.8981 (2)0.33697 (10)0.0431 (6)
C260.36517 (17)0.9391 (2)0.27647 (10)0.0416 (6)
C200.16623 (17)0.9546 (2)0.24343 (10)0.0401 (6)
C210.13790 (17)0.9886 (2)0.18364 (10)0.0435 (6)
H210.18661.00020.16320.052*
C220.03519 (19)1.0043 (3)0.15614 (11)0.0486 (6)
C270.39178 (18)1.0505 (3)0.25046 (11)0.0488 (6)
H270.34521.11920.23960.059*
C250.08992 (17)0.9379 (2)0.27223 (11)0.0435 (6)
C320.29212 (18)0.8725 (3)0.44470 (11)0.0461 (6)
C310.43626 (17)0.8379 (3)0.29185 (11)0.0497 (6)
H310.41980.76150.30890.060*
C240.01346 (18)0.9537 (3)0.24349 (11)0.0506 (7)
H240.06300.94200.26330.061*
C190.26273 (16)0.9280 (2)0.28583 (10)0.0407 (6)
C230.03975 (18)0.9869 (3)0.18481 (11)0.0533 (7)
H230.10830.99780.16420.064*
C330.3759 (2)0.8414 (3)0.54739 (11)0.0649 (8)
H33A0.41420.76620.56730.078*
H33B0.30580.83320.54920.078*
C290.5562 (2)0.9604 (3)0.25614 (12)0.0597 (8)
H290.62000.96760.24910.072*
C300.53170 (19)0.8502 (3)0.28198 (12)0.0595 (7)
H300.57930.78270.29310.071*
C340.4210 (3)0.9624 (3)0.57708 (14)0.0844 (10)
H34A0.48740.97540.57130.127*
H34B0.42740.95570.61860.127*
H34C0.37771.03550.56080.127*
C280.4867 (2)1.0605 (3)0.24051 (12)0.0600 (7)
H280.50361.13590.22300.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.06387 (18)0.05642 (19)0.0667 (2)0.01506 (14)0.00868 (14)0.00791 (15)
O10.0529 (10)0.0624 (12)0.0556 (11)0.0058 (9)0.0263 (9)0.0062 (9)
O20.0496 (9)0.0571 (12)0.0488 (11)0.0107 (8)0.0161 (8)0.0131 (9)
C30.0367 (12)0.0409 (14)0.0407 (14)0.0030 (11)0.0070 (10)0.0045 (12)
C50.0437 (13)0.0385 (15)0.0440 (15)0.0008 (11)0.0010 (11)0.0050 (12)
C90.0403 (13)0.0364 (14)0.0423 (15)0.0020 (10)0.0122 (11)0.0007 (11)
N20.0474 (11)0.0495 (13)0.0454 (13)0.0105 (10)0.0208 (10)0.0049 (10)
C150.0427 (13)0.0439 (16)0.0434 (15)0.0050 (12)0.0113 (12)0.0011 (12)
C20.0360 (12)0.0415 (14)0.0381 (14)0.0021 (10)0.0088 (10)0.0006 (12)
C40.0426 (13)0.0446 (15)0.0450 (15)0.0020 (11)0.0097 (11)0.0033 (13)
C10.0396 (13)0.0417 (15)0.0406 (14)0.0006 (11)0.0107 (11)0.0030 (12)
N10.0445 (11)0.0516 (13)0.0434 (12)0.0000 (10)0.0193 (9)0.0013 (10)
C80.0369 (12)0.0461 (15)0.0413 (14)0.0024 (11)0.0076 (11)0.0066 (12)
C70.0421 (13)0.0556 (16)0.0506 (16)0.0001 (12)0.0131 (12)0.0150 (14)
C140.0460 (14)0.0492 (16)0.0446 (16)0.0017 (12)0.0098 (11)0.0051 (13)
C60.0395 (13)0.0458 (16)0.0572 (17)0.0055 (11)0.0062 (12)0.0119 (14)
C100.0430 (13)0.0504 (16)0.0451 (15)0.0032 (11)0.0125 (11)0.0024 (12)
C130.0614 (17)0.0608 (18)0.0457 (16)0.0051 (14)0.0238 (13)0.0124 (14)
C120.0522 (16)0.0564 (17)0.066 (2)0.0054 (13)0.0304 (14)0.0061 (15)
C110.0410 (14)0.0585 (18)0.0608 (19)0.0041 (12)0.0139 (13)0.0009 (15)
C160.0601 (16)0.064 (2)0.0432 (16)0.0029 (14)0.0141 (13)0.0091 (14)
C170.0686 (18)0.0530 (18)0.0505 (17)0.0048 (14)0.0038 (13)0.0044 (14)
Br20.0711 (2)0.1016 (3)0.04400 (18)0.00474 (17)0.00264 (14)0.01354 (17)
O30.0444 (10)0.0853 (14)0.0488 (11)0.0027 (9)0.0164 (8)0.0076 (10)
N30.0416 (11)0.0637 (14)0.0391 (12)0.0035 (10)0.0151 (9)0.0039 (11)
O40.0438 (9)0.1117 (16)0.0373 (10)0.0039 (10)0.0060 (8)0.0001 (10)
N40.0403 (11)0.0737 (16)0.0396 (12)0.0062 (10)0.0118 (9)0.0031 (11)
C180.0404 (13)0.0496 (15)0.0366 (14)0.0017 (11)0.0063 (11)0.0013 (12)
C260.0432 (13)0.0478 (16)0.0330 (13)0.0027 (11)0.0092 (10)0.0050 (12)
C200.0432 (12)0.0391 (14)0.0388 (14)0.0013 (11)0.0125 (11)0.0025 (11)
C210.0492 (14)0.0436 (15)0.0394 (15)0.0009 (11)0.0153 (11)0.0038 (12)
C220.0548 (15)0.0475 (16)0.0386 (15)0.0023 (12)0.0049 (12)0.0000 (12)
C270.0488 (14)0.0491 (16)0.0506 (16)0.0040 (12)0.0171 (12)0.0016 (13)
C250.0438 (13)0.0452 (15)0.0399 (14)0.0005 (11)0.0092 (11)0.0017 (12)
C320.0421 (14)0.0560 (17)0.0409 (15)0.0064 (12)0.0128 (12)0.0047 (13)
C310.0469 (14)0.0507 (16)0.0503 (16)0.0011 (13)0.0117 (12)0.0023 (13)
C240.0411 (13)0.0612 (18)0.0512 (17)0.0013 (12)0.0155 (12)0.0039 (14)
C190.0399 (12)0.0459 (15)0.0362 (14)0.0014 (11)0.0105 (10)0.0022 (12)
C230.0409 (13)0.0639 (18)0.0494 (17)0.0031 (12)0.0032 (12)0.0018 (14)
C330.0572 (16)0.094 (2)0.0415 (16)0.0023 (16)0.0105 (13)0.0056 (16)
C290.0433 (14)0.073 (2)0.067 (2)0.0102 (15)0.0225 (13)0.0095 (16)
C300.0471 (15)0.065 (2)0.0644 (19)0.0099 (14)0.0128 (13)0.0081 (16)
C340.088 (2)0.102 (3)0.060 (2)0.010 (2)0.0156 (17)0.0146 (19)
C280.0625 (17)0.0614 (19)0.0595 (18)0.0107 (15)0.0224 (14)0.0002 (15)
Geometric parameters (Å, º) top
Br1—C51.906 (2)Br2—C221.903 (2)
O1—C151.207 (3)O3—C321.204 (3)
O2—C151.339 (3)N3—C181.371 (3)
O2—C161.443 (3)N3—C251.381 (3)
C3—C81.400 (3)N3—H30.860
C3—C41.401 (3)O4—C321.329 (3)
C3—C21.446 (3)O4—C331.448 (3)
C5—C41.375 (3)N4—C321.350 (3)
C5—C61.383 (3)N4—C181.393 (3)
C9—C141.388 (3)N4—H4A0.860
C9—C101.390 (3)C18—C191.358 (3)
C9—C21.472 (3)C26—C271.385 (3)
N2—C151.349 (3)C26—C311.390 (3)
N2—C11.394 (3)C26—C191.475 (3)
N2—H20.860C20—C211.396 (3)
C2—C11.366 (3)C20—C251.401 (3)
C4—H40.930C20—C191.435 (3)
C1—N11.358 (3)C21—C221.375 (3)
N1—C81.375 (3)C21—H210.930
N1—H10.860C22—C231.383 (3)
C8—C71.386 (3)C27—C281.379 (3)
C7—C61.380 (4)C27—H270.930
C7—H70.930C25—C241.389 (3)
C14—C131.379 (3)C31—C301.387 (3)
C14—H140.930C31—H310.930
C6—H60.930C24—C231.370 (3)
C10—C111.381 (3)C24—H240.930
C10—H100.930C23—H230.930
C13—C121.370 (3)C33—C341.464 (4)
C13—H130.930C33—H33A0.970
C12—C111.370 (3)C33—H33B0.970
C12—H120.930C29—C301.361 (4)
C11—H110.930C29—C281.368 (4)
C16—C171.487 (4)C29—H290.930
C16—H16A0.970C30—H300.930
C16—H16B0.970C34—H34A0.960
C17—H17A0.960C34—H34B0.960
C17—H17B0.960C34—H34C0.960
C17—H17C0.960C28—H280.930
C15—O2—C16115.97 (19)C18—N3—C25107.52 (19)
C8—C3—C4118.8 (2)C18—N3—H3126.2
C8—C3—C2107.3 (2)C25—N3—H3126.2
C4—C3—C2133.9 (2)C32—O4—C33118.7 (2)
C4—C5—C6123.6 (2)C32—N4—C18126.7 (2)
C4—C5—Br1119.5 (2)C32—N4—H4A116.7
C6—C5—Br1116.85 (18)C18—N4—H4A116.7
C14—C9—C10117.7 (2)C19—C18—N3111.4 (2)
C14—C9—C2121.4 (2)C19—C18—N4127.0 (2)
C10—C9—C2120.9 (2)N3—C18—N4121.5 (2)
C15—N2—C1125.3 (2)C27—C26—C31118.3 (2)
C15—N2—H2117.3C27—C26—C19120.2 (2)
C1—N2—H2117.3C31—C26—C19121.5 (2)
O1—C15—O2124.1 (2)C21—C20—C25119.1 (2)
O1—C15—N2125.9 (2)C21—C20—C19133.6 (2)
O2—C15—N2110.0 (2)C25—C20—C19107.3 (2)
C1—C2—C3105.1 (2)C22—C21—C20117.5 (2)
C1—C2—C9126.7 (2)C22—C21—H21121.3
C3—C2—C9128.2 (2)C20—C21—H21121.3
C5—C4—C3117.3 (2)C21—C22—C23123.1 (2)
C5—C4—H4121.3C21—C22—Br2118.2 (2)
C3—C4—H4121.3C23—C22—Br2118.73 (18)
N1—C1—C2111.4 (2)C28—C27—C26120.6 (2)
N1—C1—N2120.6 (2)C28—C27—H27119.7
C2—C1—N2128.0 (2)C26—C27—H27119.7
C1—N1—C8108.46 (19)N3—C25—C24129.5 (2)
C1—N1—H1125.8N3—C25—C20108.00 (19)
C8—N1—H1125.8C24—C25—C20122.4 (2)
N1—C8—C7129.3 (2)O3—C32—O4125.5 (2)
N1—C8—C3107.8 (2)O3—C32—N4125.0 (2)
C7—C8—C3122.9 (2)O4—C32—N4109.4 (2)
C6—C7—C8117.5 (2)C30—C31—C26120.3 (3)
C6—C7—H7121.2C30—C31—H31119.8
C8—C7—H7121.2C26—C31—H31119.8
C13—C14—C9121.0 (2)C23—C24—C25117.6 (2)
C13—C14—H14119.5C23—C24—H24121.2
C9—C14—H14119.5C25—C24—H24121.2
C7—C6—C5119.7 (2)C18—C19—C20105.74 (19)
C7—C6—H6120.1C18—C19—C26127.3 (2)
C5—C6—H6120.1C20—C19—C26126.8 (2)
C11—C10—C9121.1 (2)C24—C23—C22120.3 (2)
C11—C10—H10119.4C24—C23—H23119.8
C9—C10—H10119.4C22—C23—H23119.8
C12—C13—C14120.2 (2)O4—C33—C34110.0 (2)
C12—C13—H13119.9O4—C33—H33A109.7
C14—C13—H13119.9C34—C33—H33A109.7
C13—C12—C11120.1 (2)O4—C33—H33B109.7
C13—C12—H12120.0C34—C33—H33B109.7
C11—C12—H12120.0H33A—C33—H33B108.2
C12—C11—C10119.9 (2)C30—C29—C28119.7 (2)
C12—C11—H11120.1C30—C29—H29120.1
C10—C11—H11120.1C28—C29—H29120.1
O2—C16—C17108.3 (2)C29—C30—C31120.5 (3)
O2—C16—H16A110.0C29—C30—H30119.8
C17—C16—H16A110.0C31—C30—H30119.8
O2—C16—H16B110.0C33—C34—H34A109.5
C17—C16—H16B110.0C33—C34—H34B109.5
H16A—C16—H16B108.4H34A—C34—H34B109.5
C16—C17—H17A109.5C33—C34—H34C109.5
C16—C17—H17B109.5H34A—C34—H34C109.5
H17A—C17—H17B109.5H34B—C34—H34C109.5
C16—C17—H17C109.5C29—C28—C27120.6 (3)
H17A—C17—H17C109.5C29—C28—H28119.7
H17B—C17—H17C109.5C27—C28—H28119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.192.722 (3)120
N1—H1···O3i0.862.282.926 (3)132
N2—H2···O3ii0.862.483.282 (3)155
N3—H3···O30.862.332.797 (2)114
N3—H3···O1iii0.862.333.049 (3)142
C33—H33B···O30.982.372.739 (3)102
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x1/2, y+3/2, z+1/2.
 

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