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In the title compound, C16H22BrNO3, the mol­ecules are linked only by weak van der Waals inter­actions. The bromo attached cyclohexane ring adopts a half-chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002224/at6071sup1.cif
Contains datablocks global, 8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002224/at60718sup2.hkl
Contains datablock 8

CCDC reference: 298360

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.071
  • wR factor = 0.179
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.030 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.49 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14 PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C10 - C11 ... 1.21 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O2 .. 3.16 Ang.
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 26.00 From the CIF: _reflns_number_total 3327 Count of symmetry unique reflns 1938 Completeness (_total/calc) 171.67% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1389 Fraction of Friedel pairs measured 0.717 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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).

tert-Butyl N-(2-bromocyclohex-2-enyl)-N-(2-furylmethyl)carbamate top
Crystal data top
C16H22BrNO3F(000) = 736
Mr = 356.26Dx = 1.400 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 32388 reflections
a = 6.2089 (4) Åθ = 1.8–28.1°
b = 14.6385 (13) ŵ = 2.44 mm1
c = 18.5957 (12) ÅT = 293 K
V = 1690.1 (2) Å3Plate-like stick, colourless
Z = 40.61 × 0.45 × 0.20 mm
Data collection top
Stoe IPDS-2
diffractometer
3327 independent reflections
Radiation source: fine-focus sealed tube2788 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scansh = 77
Absorption correction: integration
(Reference)
k = 1818
Tmin = 0.218, Tmax = 0.567l = 2222
16581 measured reflections
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)] = 0.071H-atom parameters constrained
wR(F2) = 0.180 w = 1/[σ2(Fo2) + (0.0433P)2 + 6.2411P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
3327 reflectionsΔρmax = 0.54 e Å3
191 parametersΔρmin = 0.79 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1389 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.49 (3)
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
C10.6895 (13)0.5876 (5)0.1082 (4)0.0493 (19)
H10.77250.57790.06400.059*
C20.4717 (15)0.6262 (6)0.0880 (5)0.059 (2)
C30.4171 (18)0.7140 (6)0.0903 (6)0.076 (3)
H30.27950.73120.07600.091*
C40.571 (2)0.7853 (7)0.1153 (7)0.088 (3)
H4A0.56370.83730.08300.106*
H4B0.52840.80600.16280.106*
C50.794 (2)0.7517 (6)0.1181 (5)0.080 (3)
H5A0.88130.79400.14560.096*
H5B0.85170.74860.06970.096*
C60.804 (2)0.6566 (5)0.1529 (5)0.076 (3)
H6A0.95290.63850.15870.092*
H6B0.73810.65900.20020.092*
C70.5486 (14)0.4942 (6)0.2136 (4)0.056 (2)
H7A0.46210.43900.21330.067*
H7B0.45140.54590.21670.067*
C80.691 (2)0.4935 (6)0.2781 (4)0.077 (4)
C90.895 (2)0.4793 (8)0.2904 (6)0.084 (3)
H91.00090.46320.25730.101*
C100.919 (3)0.4930 (10)0.3602 (8)0.116 (5)
H101.05350.48980.38210.139*
C110.758 (3)0.5099 (6)0.3941 (4)0.096 (4)
H110.74740.51970.44330.116*
C120.7544 (14)0.4229 (4)0.1147 (3)0.0400 (13)
C130.8126 (14)0.2601 (5)0.1394 (4)0.059 (2)
C141.0574 (17)0.2721 (7)0.1389 (6)0.085 (3)
H14A1.10430.29340.18520.102*
H14B1.09680.31580.10280.102*
H14C1.12480.21460.12850.102*
C150.748 (2)0.2047 (5)0.2036 (5)0.079 (3)
H15A0.59350.20470.20780.095*
H15B0.80970.23080.24620.095*
H15C0.79790.14310.19790.095*
C160.733 (2)0.2237 (6)0.0706 (4)0.077 (3)
H16A0.77040.26480.03240.092*
H16B0.57880.21750.07280.092*
H16C0.79640.16500.06180.092*
N10.6706 (11)0.4998 (4)0.1459 (3)0.0485 (15)
O10.5903 (16)0.5118 (6)0.3429 (4)0.096 (3)
O20.8352 (9)0.4217 (4)0.0567 (3)0.0606 (14)
O30.7251 (12)0.3504 (3)0.1565 (2)0.0591 (14)
Br10.26213 (15)0.53883 (6)0.05276 (5)0.0707 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.062 (5)0.042 (4)0.044 (4)0.005 (3)0.004 (3)0.002 (3)
C20.064 (5)0.050 (5)0.062 (5)0.001 (4)0.005 (4)0.005 (4)
C30.077 (6)0.053 (5)0.098 (7)0.015 (5)0.011 (6)0.016 (5)
C40.113 (9)0.048 (5)0.104 (9)0.001 (6)0.005 (7)0.009 (6)
C50.109 (9)0.054 (5)0.077 (6)0.008 (6)0.013 (6)0.011 (4)
C60.127 (10)0.045 (4)0.058 (5)0.020 (5)0.023 (6)0.004 (4)
C70.061 (5)0.045 (4)0.060 (5)0.002 (4)0.001 (4)0.006 (4)
C80.156 (13)0.046 (4)0.029 (4)0.018 (6)0.008 (5)0.004 (3)
C90.107 (9)0.079 (8)0.065 (6)0.015 (7)0.018 (6)0.006 (6)
C100.135 (13)0.103 (10)0.109 (11)0.013 (9)0.031 (10)0.053 (9)
C110.193 (13)0.062 (5)0.034 (4)0.014 (10)0.007 (8)0.001 (4)
C120.041 (3)0.046 (3)0.033 (3)0.001 (4)0.008 (3)0.003 (2)
C130.076 (6)0.043 (4)0.056 (4)0.008 (4)0.001 (4)0.005 (3)
C140.083 (7)0.075 (7)0.098 (8)0.028 (6)0.001 (6)0.001 (6)
C150.109 (7)0.052 (4)0.076 (5)0.016 (6)0.014 (7)0.013 (4)
C160.101 (7)0.062 (5)0.067 (5)0.014 (7)0.001 (6)0.013 (4)
N10.064 (4)0.042 (3)0.040 (3)0.008 (3)0.001 (3)0.004 (3)
O10.125 (7)0.089 (6)0.073 (5)0.031 (5)0.001 (5)0.024 (4)
O20.081 (4)0.051 (3)0.050 (3)0.003 (3)0.011 (3)0.001 (3)
O30.094 (4)0.043 (3)0.041 (2)0.010 (3)0.008 (3)0.0016 (19)
Br10.0581 (4)0.0812 (6)0.0728 (5)0.0061 (6)0.0111 (5)0.0007 (4)
Geometric parameters (Å, º) top
C1—N11.468 (9)C9—C101.321 (16)
C1—C61.488 (11)C9—H90.9300
C1—C21.513 (12)C10—C111.21 (2)
C1—H10.9800C10—H100.9300
C2—C31.330 (12)C11—O11.412 (18)
C2—Br11.939 (9)C11—H110.9300
C3—C41.489 (16)C12—O21.189 (8)
C3—H30.9300C12—O31.328 (7)
C4—C51.469 (16)C12—N11.369 (8)
C4—H4A0.9700C13—O31.463 (9)
C4—H4B0.9700C13—C161.472 (11)
C5—C61.537 (11)C13—C151.499 (11)
C5—H5A0.9700C13—C141.530 (14)
C5—H5B0.9700C14—H14A0.9600
C6—H6A0.9700C14—H14B0.9600
C6—H6B0.9700C14—H14C0.9600
C7—N11.472 (10)C15—H15A0.9600
C7—C81.492 (13)C15—H15B0.9600
C7—H7A0.9700C15—H15C0.9600
C7—H7B0.9700C16—H16A0.9600
C8—C91.302 (17)C16—H16B0.9600
C8—O11.385 (12)C16—H16C0.9600
N1—C1—C6111.4 (6)C8—C9—H9127.6
N1—C1—C2111.9 (6)C10—C9—H9127.6
C6—C1—C2108.1 (7)C11—C10—C9116.8 (16)
N1—C1—H1108.4C11—C10—H10121.6
C6—C1—H1108.4C9—C10—H10121.6
C2—C1—H1108.4C10—C11—O1105.3 (9)
C3—C2—C1125.5 (9)C10—C11—H11127.4
C3—C2—Br1118.5 (8)O1—C11—H11127.4
C1—C2—Br1116.0 (6)O2—C12—O3125.2 (6)
C2—C3—C4121.6 (10)O2—C12—N1123.8 (6)
C2—C3—H3119.2O3—C12—N1111.0 (5)
C4—C3—H3119.2O3—C13—C16113.0 (7)
C5—C4—C3112.3 (9)O3—C13—C15102.4 (7)
C5—C4—H4A109.1C16—C13—C15113.9 (7)
C3—C4—H4A109.1O3—C13—C14105.5 (7)
C5—C4—H4B109.1C16—C13—C14111.8 (9)
C3—C4—H4B109.1C15—C13—C14109.5 (9)
H4A—C4—H4B107.9C13—C14—H14A109.5
C4—C5—C6110.9 (10)C13—C14—H14B109.5
C4—C5—H5A109.5H14A—C14—H14B109.5
C6—C5—H5A109.5C13—C14—H14C109.5
C4—C5—H5B109.5H14A—C14—H14C109.5
C6—C5—H5B109.5H14B—C14—H14C109.5
H5A—C5—H5B108.0C13—C15—H15A109.5
C1—C6—C5111.1 (7)C13—C15—H15B109.5
C1—C6—H6A109.4H15A—C15—H15B109.5
C5—C6—H6A109.4C13—C15—H15C109.5
C1—C6—H6B109.4H15A—C15—H15C109.5
C5—C6—H6B109.4H15B—C15—H15C109.5
H6A—C6—H6B108.0C13—C16—H16A109.5
N1—C7—C8112.5 (8)C13—C16—H16B109.5
N1—C7—H7A109.1H16A—C16—H16B109.5
C8—C7—H7A109.1C13—C16—H16C109.5
N1—C7—H7B109.1H16A—C16—H16C109.5
C8—C7—H7B109.1H16B—C16—H16C109.5
H7A—C7—H7B107.8C12—N1—C1119.2 (6)
C9—C8—O1108.6 (10)C12—N1—C7120.7 (6)
C9—C8—C7136.0 (11)C1—N1—C7119.9 (6)
O1—C8—C7115.3 (11)C8—O1—C11104.3 (10)
C8—C9—C10104.9 (14)C12—O3—C13122.9 (6)
N1—C1—C2—C3141.7 (9)O3—C12—N1—C1179.3 (7)
C6—C1—C2—C318.7 (12)O2—C12—N1—C7172.1 (8)
N1—C1—C2—Br140.7 (8)O3—C12—N1—C75.3 (10)
C6—C1—C2—Br1163.7 (6)C6—C1—N1—C12122.4 (8)
C1—C2—C3—C41.2 (16)C2—C1—N1—C12116.4 (8)
Br1—C2—C3—C4178.7 (8)C6—C1—N1—C762.1 (10)
C2—C3—C4—C514.8 (16)C2—C1—N1—C759.0 (9)
C3—C4—C5—C644.8 (13)C8—C7—N1—C1283.7 (9)
N1—C1—C6—C5171.6 (9)C8—C7—N1—C1100.9 (9)
C2—C1—C6—C548.2 (11)C9—C8—O1—C111.9 (13)
C4—C5—C6—C165.0 (12)C7—C8—O1—C11178.2 (8)
N1—C7—C8—C916.1 (17)C10—C11—O1—C80.1 (12)
N1—C7—C8—O1164.1 (8)O2—C12—O3—C137.4 (13)
O1—C8—C9—C102.8 (16)N1—C12—O3—C13175.2 (7)
C7—C8—C9—C10177.4 (12)C16—C13—O3—C1260.2 (11)
C8—C9—C10—C113 (2)C15—C13—O3—C12176.9 (8)
C9—C10—C11—O11.8 (17)C14—C13—O3—C1262.3 (11)
O2—C12—N1—C13.3 (12)
 

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