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The title compound, C12H15NO3, crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are within normal ranges. There are some weak inter­molecular hydrogen-bond inter­actions in the crystal structure, which provide stabilization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016387/hg6190sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016387/hg6190Isup2.hkl
Contains datablock I

CCDC reference: 274430

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.041
  • wR factor = 0.108
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.36 From the CIF: _reflns_number_total 2751 Count of symmetry unique reflns 2759 Completeness (_total/calc) 99.71% 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 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2,3-Dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate top
Crystal data top
C12H15NO3F(000) = 944
Mr = 221.25Dx = 1.230 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2998 reflections
a = 10.2654 (15) Åθ = 2.3–21.9°
b = 13.515 (2) ŵ = 0.09 mm1
c = 17.230 (3) ÅT = 294 K
V = 2390.5 (6) Å3Block, colorless
Z = 80.38 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2751 independent reflections
Radiation source: fine-focus sealed tube1787 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.956, Tmax = 0.989k = 1616
13513 measured reflectionsl = 921
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1511P]
where P = (Fo2 + 2Fc2)/3
2751 reflections(Δ/σ)max < 0.001
303 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.18 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
N10.6869 (3)0.0413 (2)0.14210 (19)0.0588 (8)
H10.616 (3)0.014 (2)0.1342 (19)0.053 (10)*
O10.9220 (2)0.16781 (16)0.01436 (13)0.0592 (6)
O20.75308 (18)0.11395 (15)0.14144 (12)0.0518 (5)
O30.9006 (2)0.00789 (16)0.15668 (17)0.0733 (8)
C11.0255 (3)0.2135 (3)0.03462 (19)0.0568 (8)
C21.0708 (3)0.3045 (3)0.0102 (2)0.0697 (10)
H2A1.16510.30680.01340.084*
H2B1.03980.36480.01420.084*
C31.0113 (3)0.2916 (2)0.08943 (19)0.0532 (8)
C40.9261 (3)0.2123 (2)0.08516 (18)0.0458 (7)
C50.8503 (3)0.1873 (2)0.14786 (18)0.0460 (7)
C60.8612 (3)0.2404 (2)0.21542 (19)0.0602 (9)
H60.81070.22360.25830.072*
C70.9469 (4)0.3184 (2)0.2198 (2)0.0692 (10)
H70.95420.35390.26580.083*
C81.0216 (4)0.3444 (2)0.1570 (2)0.0654 (10)
H81.07900.39740.16030.078*
C90.7898 (3)0.0173 (2)0.14727 (18)0.0449 (7)
C100.6948 (4)0.1469 (3)0.1498 (3)0.0907 (13)
H10A0.72640.17500.10230.136*
H10B0.60990.17300.16110.136*
H10C0.75340.16320.19130.136*
C110.9619 (5)0.2384 (3)0.1105 (2)0.1022 (15)
H11A0.92560.17950.13290.153*
H11B1.02560.26580.14520.153*
H11C0.89390.28600.10190.153*
C121.1301 (4)0.1375 (3)0.0418 (3)0.0850 (12)
H12A1.16160.12030.00890.128*
H12B1.20040.16360.07230.128*
H12C1.09560.07960.06670.128*
N20.1835 (3)1.0287 (2)0.16528 (17)0.0549 (8)
H20.110 (3)1.013 (2)0.1513 (18)0.047 (9)*
O40.3405 (2)0.72157 (16)0.11432 (12)0.0589 (6)
O50.24031 (19)0.91495 (16)0.08070 (15)0.0628 (6)
O60.3972 (2)0.99699 (19)0.14612 (15)0.0738 (8)
C130.3986 (3)0.6209 (2)0.10702 (19)0.0554 (8)
C140.4916 (4)0.6269 (3)0.0374 (2)0.0700 (10)
H14A0.58170.62340.05400.084*
H14B0.47480.57390.00080.084*
C150.4615 (3)0.7261 (2)0.00202 (18)0.0508 (8)
C160.3762 (3)0.7746 (2)0.05047 (17)0.0460 (7)
C170.3338 (3)0.8692 (2)0.03366 (19)0.0510 (8)
C180.3783 (3)0.9136 (3)0.0329 (2)0.0652 (10)
H180.35090.97730.04520.078*
C190.4635 (3)0.8648 (3)0.0819 (2)0.0697 (10)
H190.49240.89570.12690.084*
C200.5060 (3)0.7702 (3)0.06431 (19)0.0589 (9)
H200.56370.73730.09700.071*
C210.2843 (3)0.9826 (2)0.13303 (19)0.0464 (8)
C220.1983 (4)1.1012 (3)0.2258 (2)0.0882 (13)
H22A0.21631.06840.27400.132*
H22B0.11941.13880.23060.132*
H22C0.26911.14470.21320.132*
C230.4693 (4)0.6034 (3)0.1824 (2)0.0871 (12)
H23A0.53070.65580.19100.131*
H23B0.51460.54130.18000.131*
H23C0.40760.60190.22430.131*
C240.2879 (4)0.5509 (3)0.0941 (3)0.0995 (16)
H24A0.23410.54890.13970.149*
H24B0.32160.48590.08380.149*
H24C0.23710.57280.05060.149*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0316 (15)0.0554 (18)0.089 (2)0.0056 (13)0.0006 (15)0.0017 (16)
O10.0518 (12)0.0697 (14)0.0560 (13)0.0237 (11)0.0085 (10)0.0013 (12)
O20.0304 (9)0.0533 (13)0.0718 (14)0.0008 (9)0.0011 (10)0.0155 (12)
O30.0314 (11)0.0564 (14)0.132 (2)0.0009 (10)0.0106 (13)0.0107 (15)
C10.0527 (18)0.0619 (19)0.0559 (19)0.0133 (17)0.0061 (15)0.0107 (17)
C20.064 (2)0.067 (2)0.078 (2)0.0203 (19)0.0159 (19)0.003 (2)
C30.0466 (17)0.0450 (17)0.068 (2)0.0071 (15)0.0032 (16)0.0034 (17)
C40.0389 (15)0.0473 (16)0.0511 (18)0.0005 (14)0.0002 (14)0.0038 (16)
C50.0356 (15)0.0437 (16)0.0587 (19)0.0003 (13)0.0026 (15)0.0084 (15)
C60.0606 (19)0.061 (2)0.059 (2)0.0023 (18)0.0102 (17)0.0076 (18)
C70.081 (2)0.059 (2)0.067 (2)0.011 (2)0.008 (2)0.0071 (18)
C80.072 (2)0.0426 (18)0.082 (3)0.0162 (17)0.003 (2)0.0044 (18)
C90.0315 (16)0.0498 (18)0.0533 (18)0.0009 (13)0.0021 (14)0.0066 (16)
C100.061 (2)0.057 (2)0.154 (4)0.0084 (19)0.003 (3)0.001 (3)
C110.111 (3)0.112 (4)0.084 (3)0.033 (3)0.019 (3)0.041 (3)
C120.062 (2)0.068 (2)0.125 (3)0.002 (2)0.030 (2)0.011 (2)
N20.0303 (14)0.0608 (17)0.0737 (19)0.0004 (12)0.0003 (13)0.0083 (15)
O40.0610 (13)0.0579 (13)0.0578 (13)0.0171 (12)0.0167 (11)0.0018 (11)
O50.0326 (10)0.0522 (13)0.1035 (18)0.0013 (10)0.0024 (12)0.0238 (13)
O60.0309 (11)0.0996 (19)0.0910 (18)0.0006 (12)0.0026 (12)0.0327 (15)
C130.0469 (18)0.0548 (19)0.065 (2)0.0125 (16)0.0070 (16)0.0032 (17)
C140.076 (2)0.067 (2)0.068 (2)0.025 (2)0.020 (2)0.0036 (19)
C150.0423 (16)0.0581 (19)0.0520 (18)0.0032 (15)0.0019 (15)0.0081 (16)
C160.0374 (15)0.0516 (18)0.0489 (17)0.0013 (14)0.0013 (14)0.0047 (16)
C170.0299 (14)0.0475 (18)0.076 (2)0.0016 (14)0.0056 (15)0.0102 (17)
C180.0422 (18)0.061 (2)0.093 (3)0.0012 (17)0.0076 (19)0.014 (2)
C190.0503 (19)0.089 (3)0.070 (2)0.002 (2)0.0010 (19)0.022 (2)
C200.0426 (17)0.083 (2)0.0515 (19)0.0044 (18)0.0056 (15)0.0058 (18)
C210.0302 (16)0.0474 (17)0.0617 (19)0.0008 (13)0.0033 (14)0.0008 (16)
C220.061 (2)0.120 (3)0.084 (3)0.003 (2)0.005 (2)0.039 (3)
C230.080 (3)0.100 (3)0.082 (3)0.025 (3)0.007 (2)0.010 (2)
C240.060 (2)0.072 (3)0.167 (5)0.001 (2)0.008 (3)0.030 (3)
Geometric parameters (Å, º) top
N1—C91.324 (4)N2—C211.329 (4)
N1—C101.435 (4)N2—C221.439 (4)
N1—H10.82 (3)N2—H20.82 (3)
O1—C41.361 (4)O4—C161.363 (3)
O1—C11.491 (4)O4—C131.491 (4)
O2—C91.363 (4)O5—C211.362 (4)
O2—C51.411 (3)O5—C171.400 (4)
O3—C91.199 (3)O6—C211.196 (3)
C1—C121.492 (5)C13—C241.495 (5)
C1—C111.499 (5)C13—C231.507 (5)
C1—C21.525 (5)C13—C141.536 (5)
C2—C31.505 (5)C14—C151.505 (5)
C2—H2A0.9700C14—H14A0.9700
C2—H2B0.9700C14—H14B0.9700
C3—C81.369 (4)C15—C201.367 (4)
C3—C41.386 (4)C15—C161.377 (4)
C4—C51.374 (4)C16—C171.381 (4)
C5—C61.372 (4)C17—C181.373 (5)
C6—C71.375 (4)C18—C191.383 (5)
C6—H60.9300C18—H180.9300
C7—C81.372 (5)C19—C201.385 (5)
C7—H70.9300C19—H190.9300
C8—H80.9300C20—H200.9300
C10—H10A0.9600C22—H22A0.9600
C10—H10B0.9600C22—H22B0.9600
C10—H10C0.9600C22—H22C0.9600
C11—H11A0.9600C23—H23A0.9600
C11—H11B0.9600C23—H23B0.9600
C11—H11C0.9600C23—H23C0.9600
C12—H12A0.9600C24—H24A0.9600
C12—H12B0.9600C24—H24B0.9600
C12—H12C0.9600C24—H24C0.9600
C9—N1—C10122.9 (3)C21—N2—C22122.7 (3)
C9—N1—H1117 (2)C21—N2—H2118 (2)
C10—N1—H1120 (2)C22—N2—H2119 (2)
C4—O1—C1107.6 (2)C16—O4—C13107.7 (2)
C9—O2—C5118.2 (2)C21—O5—C17116.9 (2)
O1—C1—C12105.9 (3)O4—C13—C24106.6 (3)
O1—C1—C11106.1 (3)O4—C13—C23105.3 (3)
C12—C1—C11113.3 (3)C24—C13—C23113.3 (3)
O1—C1—C2105.4 (3)O4—C13—C14105.5 (2)
C12—C1—C2112.3 (3)C24—C13—C14112.9 (3)
C11—C1—C2113.2 (3)C23—C13—C14112.5 (3)
C3—C2—C1104.0 (3)C15—C14—C13103.6 (3)
C3—C2—H2A111.0C15—C14—H14A111.0
C1—C2—H2A111.0C13—C14—H14A111.0
C3—C2—H2B111.0C15—C14—H14B111.0
C1—C2—H2B111.0C13—C14—H14B111.0
H2A—C2—H2B109.0H14A—C14—H14B109.0
C8—C3—C4119.8 (3)C20—C15—C16120.8 (3)
C8—C3—C2132.8 (3)C20—C15—C14131.1 (3)
C4—C3—C2107.3 (3)C16—C15—C14108.0 (3)
O1—C4—C5125.4 (3)O4—C16—C15114.2 (3)
O1—C4—C3114.1 (3)O4—C16—C17124.8 (3)
C5—C4—C3120.4 (3)C15—C16—C17120.9 (3)
C6—C5—C4119.5 (3)C18—C17—C16118.4 (3)
C6—C5—O2119.4 (3)C18—C17—O5121.2 (3)
C4—C5—O2120.8 (3)C16—C17—O5120.2 (3)
C5—C6—C7119.9 (3)C17—C18—C19120.8 (3)
C5—C6—H6120.0C17—C18—H18119.6
C7—C6—H6120.0C19—C18—H18119.6
C8—C7—C6120.8 (3)C18—C19—C20120.4 (3)
C8—C7—H7119.6C18—C19—H19119.8
C6—C7—H7119.6C20—C19—H19119.8
C3—C8—C7119.6 (3)C15—C20—C19118.7 (3)
C3—C8—H8120.2C15—C20—H20120.7
C7—C8—H8120.2C19—C20—H20120.7
O3—C9—N1126.6 (3)O6—C21—N2126.8 (3)
O3—C9—O2123.0 (3)O6—C21—O5123.7 (3)
N1—C9—O2110.4 (2)N2—C21—O5109.5 (2)
N1—C10—H10A109.5N2—C22—H22A109.5
N1—C10—H10B109.5N2—C22—H22B109.5
H10A—C10—H10B109.5H22A—C22—H22B109.5
N1—C10—H10C109.5N2—C22—H22C109.5
H10A—C10—H10C109.5H22A—C22—H22C109.5
H10B—C10—H10C109.5H22B—C22—H22C109.5
C1—C11—H11A109.5C13—C23—H23A109.5
C1—C11—H11B109.5C13—C23—H23B109.5
H11A—C11—H11B109.5H23A—C23—H23B109.5
C1—C11—H11C109.5C13—C23—H23C109.5
H11A—C11—H11C109.5H23A—C23—H23C109.5
H11B—C11—H11C109.5H23B—C23—H23C109.5
C1—C12—H12A109.5C13—C24—H24A109.5
C1—C12—H12B109.5C13—C24—H24B109.5
H12A—C12—H12B109.5H24A—C24—H24B109.5
C1—C12—H12C109.5C13—C24—H24C109.5
H12A—C12—H12C109.5H24A—C24—H24C109.5
H12B—C12—H12C109.5H24B—C24—H24C109.5
C4—O1—C1—C12107.4 (3)C16—O4—C13—C24111.2 (3)
C4—O1—C1—C11131.9 (3)C16—O4—C13—C23128.2 (3)
C4—O1—C1—C211.7 (3)C16—O4—C13—C149.1 (3)
O1—C1—C2—C312.2 (3)O4—C13—C14—C159.4 (3)
C12—C1—C2—C3102.6 (3)C24—C13—C14—C15106.6 (3)
C11—C1—C2—C3127.6 (3)C23—C13—C14—C15123.6 (3)
C1—C2—C3—C8175.3 (4)C13—C14—C15—C20174.7 (3)
C1—C2—C3—C48.8 (4)C13—C14—C15—C166.8 (3)
C1—O1—C4—C5176.5 (3)C13—O4—C16—C155.1 (3)
C1—O1—C4—C36.5 (3)C13—O4—C16—C17175.4 (3)
C8—C3—C4—O1178.3 (3)C20—C15—C16—O4179.9 (3)
C2—C3—C4—O11.7 (4)C14—C15—C16—O41.3 (4)
C8—C3—C4—C51.1 (4)C20—C15—C16—C170.4 (4)
C2—C3—C4—C5175.5 (3)C14—C15—C16—C17178.3 (3)
O1—C4—C5—C6177.9 (3)O4—C16—C17—C18179.9 (3)
C3—C4—C5—C61.1 (4)C15—C16—C17—C180.4 (4)
O1—C4—C5—O23.9 (4)O4—C16—C17—O54.8 (4)
C3—C4—C5—O2172.9 (3)C15—C16—C17—O5175.7 (3)
C9—O2—C5—C6103.9 (3)C21—O5—C17—C1883.5 (4)
C9—O2—C5—C482.1 (4)C21—O5—C17—C16101.3 (3)
C4—C5—C6—C70.4 (5)C16—C17—C18—C190.0 (5)
O2—C5—C6—C7173.7 (3)O5—C17—C18—C19175.2 (3)
C5—C6—C7—C80.3 (5)C17—C18—C19—C200.4 (5)
C4—C3—C8—C70.4 (5)C16—C15—C20—C190.0 (5)
C2—C3—C8—C7175.2 (4)C14—C15—C20—C19178.3 (3)
C6—C7—C8—C30.3 (5)C18—C19—C20—C150.4 (5)
C10—N1—C9—O32.1 (6)C22—N2—C21—O63.6 (5)
C10—N1—C9—O2177.1 (3)C22—N2—C21—O5176.9 (3)
C5—O2—C9—O30.9 (5)C17—O5—C21—O68.0 (5)
C5—O2—C9—N1178.3 (3)C17—O5—C21—N2171.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O6i0.82 (3)2.26 (3)3.020 (4)153 (3)
N2—H2···O3ii0.82 (3)2.17 (3)2.949 (4)159 (3)
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z.
 

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