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The crystal structure of the title compound, C14H14N4O3, confirms both the sites of attachment and the trans arrangement of the hydroxy and azide substituents, and reveals intermolecular hydrogen bonding between OH and C=O units, resulting in a chain of molecules along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000231/su6146sup1.cif
Contains datablocks global, 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000231/su61466sup2.hkl
Contains datablock 6

CCDC reference: 263675

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.083
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - N2 .. 6.46 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.99 From the CIF: _reflns_number_total 1968 Count of symmetry unique reflns 1969 Completeness (_total/calc) 99.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXTL.

(1R,2R)-Ethyl 1-azido-2-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate top
Crystal data top
C14H14N4O3Dx = 1.366 Mg m3
Mr = 286.29Melting point: 402.5 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 809 reflections
a = 5.8464 (9) Åθ = 2.8–24.4°
b = 8.8422 (14) ŵ = 0.10 mm1
c = 26.927 (4) ÅT = 293 K
V = 1392.0 (4) Å3Plate, yellow–brown
Z = 40.40 × 0.24 × 0.10 mm
F(000) = 600
Data collection top
Bruker SMART CCD area-detector
diffractometer
1439 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 28.0°, θmin = 1.5°
φ and ω scansh = 77
9551 measured reflectionsk = 119
1968 independent reflectionsl = 3533
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0435P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.005
1968 reflectionsΔρmax = 0.15 e Å3
196 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0084 (19)
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
C10.3739 (4)0.26103 (19)0.08722 (6)0.0412 (4)
H10.53870.24120.08890.049*
C20.3150 (3)0.4231 (2)0.10428 (7)0.0418 (5)
H20.30740.49220.07590.050*
C30.0807 (4)0.4099 (2)0.12984 (7)0.0447 (5)
H3A0.07050.47610.15850.054*
H3B0.04290.43310.10710.054*
C4A0.0537 (3)0.1628 (2)0.17635 (6)0.0390 (4)
C50.2414 (4)0.2003 (2)0.20535 (7)0.0485 (5)
H50.30080.29780.20560.058*
C60.3362 (4)0.0874 (3)0.23380 (8)0.0567 (6)
H60.46240.10870.25360.068*
C70.2457 (4)0.0589 (2)0.23335 (8)0.0569 (6)
H70.31210.13250.25340.068*
C80.0614 (4)0.0972 (2)0.20424 (7)0.0489 (5)
H80.00440.19550.20420.059*
C8A0.0389 (4)0.0153 (2)0.17457 (6)0.0391 (4)
C90.2288 (4)0.01867 (19)0.14045 (6)0.0379 (4)
C9A0.2433 (3)0.16560 (19)0.12315 (6)0.0361 (4)
C100.3725 (4)0.1082 (2)0.12739 (7)0.0416 (5)
C110.6914 (4)0.1913 (2)0.07992 (8)0.0549 (6)
H11A0.60440.27310.06510.066*
H11B0.77510.23100.10820.066*
C120.8524 (5)0.1263 (3)0.04293 (9)0.0690 (7)
H12A0.76850.09270.01430.103*
H12B0.96110.20200.03310.103*
H12C0.93170.04210.05740.103*
N10.2846 (4)0.2472 (2)0.03570 (6)0.0609 (6)
N20.3108 (3)0.1267 (2)0.01436 (6)0.0529 (5)
N30.3227 (4)0.0230 (2)0.00996 (8)0.0761 (7)
N40.0774 (3)0.25006 (16)0.14463 (5)0.0399 (4)
O10.4886 (3)0.46778 (16)0.13778 (6)0.0525 (4)
O20.3448 (3)0.23589 (14)0.14310 (5)0.0606 (4)
O30.5397 (3)0.07109 (14)0.09559 (5)0.0487 (4)
H1A0.464 (4)0.559 (3)0.1427 (7)0.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0490 (11)0.0291 (9)0.0454 (10)0.0003 (9)0.0058 (9)0.0018 (8)
C20.0520 (12)0.0250 (9)0.0485 (10)0.0019 (9)0.0001 (10)0.0054 (8)
C30.0533 (12)0.0270 (9)0.0538 (10)0.0075 (9)0.0017 (10)0.0037 (9)
C4A0.0418 (10)0.0342 (9)0.0410 (9)0.0008 (9)0.0003 (9)0.0004 (8)
C50.0437 (11)0.0505 (12)0.0514 (11)0.0066 (10)0.0042 (10)0.0008 (9)
C60.0498 (13)0.0658 (15)0.0546 (11)0.0001 (12)0.0078 (11)0.0027 (11)
C70.0607 (14)0.0550 (14)0.0549 (11)0.0106 (12)0.0080 (12)0.0120 (10)
C80.0601 (13)0.0372 (10)0.0495 (10)0.0056 (11)0.0000 (11)0.0062 (9)
C8A0.0445 (11)0.0330 (10)0.0399 (9)0.0014 (9)0.0033 (9)0.0001 (8)
C90.0479 (11)0.0257 (9)0.0401 (9)0.0006 (8)0.0000 (9)0.0003 (7)
C9A0.0431 (10)0.0277 (9)0.0377 (9)0.0003 (9)0.0007 (9)0.0040 (8)
C100.0525 (12)0.0288 (10)0.0436 (10)0.0004 (9)0.0002 (10)0.0025 (8)
C110.0630 (15)0.0410 (11)0.0607 (12)0.0074 (11)0.0101 (12)0.0105 (10)
C120.0609 (15)0.0678 (16)0.0782 (15)0.0012 (13)0.0157 (14)0.0095 (13)
N10.0961 (16)0.0436 (10)0.0430 (9)0.0084 (12)0.0007 (10)0.0004 (8)
N20.0620 (13)0.0513 (11)0.0454 (9)0.0090 (9)0.0077 (9)0.0022 (9)
N30.0973 (19)0.0649 (13)0.0660 (12)0.0099 (14)0.0049 (12)0.0215 (11)
N40.0456 (9)0.0274 (8)0.0466 (8)0.0041 (8)0.0032 (8)0.0032 (7)
O10.0547 (9)0.0273 (7)0.0754 (9)0.0029 (6)0.0061 (8)0.0032 (7)
O20.0778 (11)0.0246 (7)0.0793 (10)0.0048 (8)0.0217 (9)0.0060 (7)
O30.0599 (9)0.0304 (7)0.0559 (7)0.0041 (7)0.0136 (7)0.0003 (6)
Geometric parameters (Å, º) top
C1—N11.487 (2)C8—C8A1.405 (3)
C1—C9A1.494 (2)C8—H80.9300
C1—C21.544 (2)C8A—C91.441 (3)
C1—H10.9800C9—C9A1.383 (2)
C2—O11.414 (2)C9—C101.445 (3)
C2—C31.537 (3)C9A—N41.354 (2)
C2—H20.9800C10—O21.216 (2)
C3—N41.469 (2)C10—O31.341 (2)
C3—H3A0.9700C11—O31.447 (2)
C3—H3B0.9700C11—C121.486 (3)
C4A—N41.382 (2)C11—H11A0.9700
C4A—C51.387 (3)C11—H11B0.9700
C4A—C8A1.413 (2)C12—H12A0.9600
C5—C61.375 (3)C12—H12B0.9600
C5—H50.9300C12—H12C0.9600
C6—C71.397 (3)N1—N21.220 (2)
C6—H60.9300N2—N31.129 (2)
C7—C81.375 (3)O1—H1A0.83 (2)
C7—H70.9300
N1—C1—C9A112.23 (16)C8A—C8—H8120.8
N1—C1—C2106.00 (15)C8—C8A—C4A118.36 (17)
C9A—C1—C2102.57 (14)C8—C8A—C9134.32 (17)
N1—C1—H1111.8C4A—C8A—C9107.31 (15)
C9A—C1—H1111.8C9A—C9—C8A106.35 (16)
C2—C1—H1111.8C9A—C9—C10127.71 (18)
O1—C2—C3112.02 (15)C8A—C9—C10125.94 (16)
O1—C2—C1106.78 (16)N4—C9A—C9109.28 (16)
C3—C2—C1105.16 (16)N4—C9A—C1109.35 (15)
O1—C2—H2110.9C9—C9A—C1141.30 (18)
C3—C2—H2110.9O2—C10—O3123.11 (17)
C1—C2—H2110.9O2—C10—C9123.97 (19)
N4—C3—C2101.91 (15)O3—C10—C9112.92 (15)
N4—C3—H3A111.4O3—C11—C12107.40 (18)
C2—C3—H3A111.4O3—C11—H11A110.2
N4—C3—H3B111.4C12—C11—H11A110.2
C2—C3—H3B111.4O3—C11—H11B110.2
H3A—C3—H3B109.3C12—C11—H11B110.2
N4—C4A—C5130.79 (18)H11A—C11—H11B108.5
N4—C4A—C8A106.36 (16)C11—C12—H12A109.5
C5—C4A—C8A122.84 (18)C11—C12—H12B109.5
C6—C5—C4A117.35 (19)H12A—C12—H12B109.5
C6—C5—H5121.3C11—C12—H12C109.5
C4A—C5—H5121.3H12A—C12—H12C109.5
C5—C6—C7121.0 (2)H12B—C12—H12C109.5
C5—C6—H6119.5N2—N1—C1117.84 (18)
C7—C6—H6119.5N3—N2—N1172.0 (2)
C8—C7—C6122.0 (2)C9A—N4—C4A110.69 (14)
C8—C7—H7119.0C9A—N4—C3113.92 (15)
C6—C7—H7119.0C4A—N4—C3135.38 (16)
C7—C8—C8A118.5 (2)C2—O1—H1A104.6 (16)
C7—C8—H8120.8C10—O3—C11116.95 (15)
N1—C1—C2—O1149.18 (16)C10—C9—C9A—C13.7 (4)
C9A—C1—C2—O192.98 (18)N1—C1—C9A—N494.40 (18)
N1—C1—C2—C391.65 (18)C2—C1—C9A—N418.93 (19)
C9A—C1—C2—C326.20 (19)N1—C1—C9A—C982.1 (3)
O1—C2—C3—N491.76 (18)C2—C1—C9A—C9164.6 (2)
C1—C2—C3—N423.86 (19)C9A—C9—C10—O2177.7 (2)
N4—C4A—C5—C6179.6 (2)C8A—C9—C10—O22.1 (3)
C8A—C4A—C5—C61.0 (3)C9A—C9—C10—O31.8 (3)
C4A—C5—C6—C70.1 (3)C8A—C9—C10—O3178.47 (17)
C5—C6—C7—C80.9 (3)C9A—C1—N1—N268.4 (3)
C6—C7—C8—C8A0.6 (3)C2—C1—N1—N2179.64 (19)
C7—C8—C8A—C4A0.4 (3)C9—C9A—N4—C4A0.6 (2)
C7—C8—C8A—C9179.6 (2)C1—C9A—N4—C4A177.10 (15)
N4—C4A—C8A—C8179.18 (16)C9—C9A—N4—C3178.47 (17)
C5—C4A—C8A—C81.2 (3)C1—C9A—N4—C33.9 (2)
N4—C4A—C8A—C90.26 (19)C5—C4A—N4—C9A179.04 (19)
C5—C4A—C8A—C9179.33 (17)C8A—C4A—N4—C9A0.5 (2)
C8—C8A—C9—C9A179.4 (2)C5—C4A—N4—C32.2 (4)
C4A—C8A—C9—C9A0.1 (2)C8A—C4A—N4—C3178.2 (2)
C8—C8A—C9—C100.8 (3)C2—C3—N4—C9A13.0 (2)
C4A—C8A—C9—C10179.87 (19)C2—C3—N4—C4A165.66 (19)
C8A—C9—C9A—N40.4 (2)O2—C10—O3—C110.1 (3)
C10—C9—C9A—N4179.83 (18)C9—C10—O3—C11179.40 (17)
C8A—C9—C9A—C1176.1 (2)C12—C11—O3—C10176.76 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.83 (2)1.94 (2)2.7553 (19)166 (2)
Symmetry code: (i) x, y+1, z.
 

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