share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2011). E67, o224
https://doi.org/10.1107/S1600536810051743
Download PDF of article
Download PDF of articleclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

tert-Butyl 4-(4-chloro­anilino)-6-methyl-2-oxocyclo­hex-3-ene­carboxyl­ate

M. S. Alexander, H. North, K. R. Scott and R. J. Butcher
In the title compound, C18H22ClNO3, the dihedral angle between the benzene ring and the conjugated part of the enaminone ring is 55.19 (9)°. The ester substituent makes a dihedral angle of 81.0 (2)° with this latter moiety. The crystal structure features N—H...O and weak C—H...O inter­molecular inter­actions.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810051743/om2378sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810051743/om2378Isup2.hkl
Contains datablock I

CCDC reference: 807459

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.172
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O1      ..       2.63 Ang.
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        H10
                    C14    C10    H10
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        H10
                    C11    C10    H10
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........        H10
                    C9     C10    H10
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........        H10
                    C10    H10
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........        H10
                    H10    O2
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........        H10
                    C10    H10    O2
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         55


Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.11
PLAT793_ALERT_4_G The Model has Chirality at C9      (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C10     (Verify) ....          S


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 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
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Our research on enaminones has led to several compounds possessing anticonvulsant properties (Edafiogho et al., 1992; Eddington et al., 2003; Scott et al., 1993, 1995). The present work is part of a structural study of enaminones. Our group has extensively studied the effects of modification of the enaminone with substitutions at the methyl ester, ethyl ester, and without the ester group. We synthesized a series of carbo-tert-butoxy esters to evaluate the effect of added bulk and lipophilicity to the ester functionality. These compounds showed significant anticonvulsant activity. The title compound, tert-butyl- 4-(4-chlorophenlyamino)-6-methyl-2-oxocyclohex-3-enecarboxylate is highly active, with activity at <100 mg kg-1. The compound was active in maximal electroshock seizure evaluation (MES) in mice, indicative of protection against tonic-clonic convulsions in humans (1/4 rats protected at 1 h, 2 h and 4 h post dose at 50 mg kg dose). Toxicity tests showed no toxicity in rats (oral) up to 4 h at 50 mg/kg per dose. The MES study in mice showed 1/1 animals were protected at 300 mg/kg at 30 minutes. In 4 h testing, 3/3 animals were protected at 100 mg/kg and 1/1 animals protected at 300 mg/kg dose. In toxicity studies, at 15 min, 2/8 mice (ip = interperitoneal) showed toxicity at 500 mg/kg dose. A 2 h MES protection test in mice (ip) displayed 3/8 animals protected at 85 mg/kg dose, 4/8 animals protected at 100 mg/kg, and 7/8 animals were protected at 170 mg/kg (optimum dose). In mice, the MES ED50 (median effective dose) of 106.34 mg kg-1 and TD50 (median toxic dose) of 500 mg kg-1 TD, 95% confidence inteval. The scMET (subcuntaneous metrazole) test showed no protection at 250 or 500 mg/kg during a 2 h range.

In view of the therapeutic interest in this compound its structure was determined. The conformation adopted by the molecule is such that the dihedral angle between the phenyl ring and conjugated part of the enaminone ring is 55.19 (9)°. The ester substituent makes a dihedral angle of 81.0 (2)° with this latter moiety. The crystal structure is held together by strong N—H···O and weak C—H···O intermolecular interactions.

Related literature top

Our research on enaminones has led to several compounds possessing

anticonvulsant properties, see: Edafiogho et al. (1992); Eddington et al. (2003); Scott et al. (1993, 1995).

Experimental top

4-Carbo-tert-butoxy-5-methylcyclohexane-1,3-dione (6. 11 g, 27 mmol), mp 145–146° C (lit. mp 130–131.5°C),7 and 4-chloroaniline (4.21 g, 33 mmol) were added to a mixture of absolute EtOH (100 ml) and EtOAc (100 ml), and the solution was refluxed and stirred for 6 h. Evaporation under reduced pressure yielded a yellow solid which was recrystallized from 2-PrOH: yield 3.96 g (43%); mp 190–192° C; 1H NMR (CDC13) 6 1.10 (3H, d, J = 6.3 Hz, CH3), 1.48 (9H, s, 3 x CH3 of tert-butyl group), 2.22–2.63 (3H, m, CH2 + CH of cyclohexene ring), 2.90 (lH, d, J =11.0 Hz, CHI, 5.45 (lH, 8, =CHI, 6.90 (lH, bs, NH), 7.05–7.30 (4H, m, C6H4).

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distance of 0.93 and 0.98 Å Uiso(H) = 1.2Ueq(C) and 0.96 Å for CH3 [Uiso(H) = 1.5Ueq(C)]. The H atoms attached to N were idealized with an N–H distance of 0.86 Å.

Structure description top

Our research on enaminones has led to several compounds possessing anticonvulsant properties (Edafiogho et al., 1992; Eddington et al., 2003; Scott et al., 1993, 1995). The present work is part of a structural study of enaminones. Our group has extensively studied the effects of modification of the enaminone with substitutions at the methyl ester, ethyl ester, and without the ester group. We synthesized a series of carbo-tert-butoxy esters to evaluate the effect of added bulk and lipophilicity to the ester functionality. These compounds showed significant anticonvulsant activity. The title compound, tert-butyl- 4-(4-chlorophenlyamino)-6-methyl-2-oxocyclohex-3-enecarboxylate is highly active, with activity at <100 mg kg-1. The compound was active in maximal electroshock seizure evaluation (MES) in mice, indicative of protection against tonic-clonic convulsions in humans (1/4 rats protected at 1 h, 2 h and 4 h post dose at 50 mg kg dose). Toxicity tests showed no toxicity in rats (oral) up to 4 h at 50 mg/kg per dose. The MES study in mice showed 1/1 animals were protected at 300 mg/kg at 30 minutes. In 4 h testing, 3/3 animals were protected at 100 mg/kg and 1/1 animals protected at 300 mg/kg dose. In toxicity studies, at 15 min, 2/8 mice (ip = interperitoneal) showed toxicity at 500 mg/kg dose. A 2 h MES protection test in mice (ip) displayed 3/8 animals protected at 85 mg/kg dose, 4/8 animals protected at 100 mg/kg, and 7/8 animals were protected at 170 mg/kg (optimum dose). In mice, the MES ED50 (median effective dose) of 106.34 mg kg-1 and TD50 (median toxic dose) of 500 mg kg-1 TD, 95% confidence inteval. The scMET (subcuntaneous metrazole) test showed no protection at 250 or 500 mg/kg during a 2 h range.

In view of the therapeutic interest in this compound its structure was determined. The conformation adopted by the molecule is such that the dihedral angle between the phenyl ring and conjugated part of the enaminone ring is 55.19 (9)°. The ester substituent makes a dihedral angle of 81.0 (2)° with this latter moiety. The crystal structure is held together by strong N—H···O and weak C—H···O intermolecular interactions.

Our research on enaminones has led to several compounds possessing

anticonvulsant properties, see: Edafiogho et al. (1992); Eddington et al. (2003); Scott et al. (1993, 1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Diagram of tert-butyl- 4-(4-chlorophenlyamino)-6-methyl-2-oxocyclohex-3-enecarboxylate showing atom labeling scheme. Thermal ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing for tert-butyl- 4-(4-chlorophenlyamino)-6-methyl-2-oxocyclohex-3-enecarboxylate viewed down the a axis. Intermolecular interactions are shown by dashed lines.
tert-Butyl 4-(4-chloroanilino)-6-methyl-2-oxocyclohex-3-enecarboxylate top
Crystal data top
C18H22ClNO3Dx = 1.262 Mg m−3
Mr = 335.82Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 5335 reflections
a = 11.0801 (3) Åθ = 4.5–77.5°
b = 10.9095 (3) ŵ = 0.23 mm−1
c = 29.2474 (7) ÅT = 295 K
V = 3535.39 (16) Å3Plate, colorless
Z = 80.45 × 0.38 × 0.08 mm
F(000) = 1424
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		3708 independent reflections
Radiation source: Enhance (Cu) X-ray Source2925 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 10.5081 pixels mm-1θmax = 26.8°, θmin = 2.3°
ω scansh = −13→14
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		k = −13→7
Tmin = 0.93, Tmax = 0.98l = −22→36
9798 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1062P)2 + 0.3243P]
where P = (Fo2 + 2Fc2)/3
3708 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C18H22ClNO3V = 3535.39 (16) Å3
Mr = 335.82Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.0801 (3) ŵ = 0.23 mm−1
b = 10.9095 (3) ÅT = 295 K
c = 29.2474 (7) Å0.45 × 0.38 × 0.08 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		3708 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		2925 reflections with I > 2σ(I)
Tmin = 0.93, Tmax = 0.98Rint = 0.030
9798 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.09Δρmax = 0.39 e Å−3
3708 reflectionsΔρmin = −0.25 e Å−3
212 parameters
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
Cl10.91865 (8)0.65446 (7)0.66441 (3)0.0944 (3)
O10.91038 (13)0.17651 (17)0.43476 (6)0.0689 (4)
O20.7403 (2)0.01470 (14)0.37719 (6)0.0785 (5)
O30.78836 (13)0.16309 (12)0.32703 (4)0.0545 (3)
N10.63017 (13)0.40873 (17)0.52106 (5)0.0539 (4)
H10.55360.41800.52430.065*
C10.70410 (16)0.46315 (18)0.55484 (6)0.0492 (4)
C20.8068 (2)0.5287 (2)0.54365 (7)0.0628 (5)
H20.83140.53330.51330.075*
C30.8732 (2)0.5875 (2)0.57713 (8)0.0682 (6)
H30.94290.63050.56950.082*
C40.8349 (2)0.5817 (2)0.62193 (7)0.0621 (5)
C50.7323 (2)0.5180 (2)0.63334 (7)0.0659 (5)
H50.70680.51540.66360.079*
C60.66736 (17)0.4583 (2)0.60016 (6)0.0584 (5)
H60.59850.41440.60810.070*
C70.66666 (15)0.34364 (17)0.48417 (5)0.0447 (4)
C80.56893 (15)0.32234 (19)0.44950 (6)0.0507 (4)
H8A0.56010.39560.43100.061*
H8B0.49330.30910.46540.061*
C90.59232 (15)0.21420 (18)0.41826 (6)0.0489 (4)
H90.58730.13910.43650.059*
C100.72128 (15)0.22487 (16)0.39930 (6)0.0447 (4)
H10A0.72700.30160.38200.054*
C110.81263 (14)0.23012 (17)0.43840 (6)0.0472 (4)
C120.78047 (15)0.29974 (18)0.47760 (6)0.0485 (4)
H120.83910.31590.49950.058*
C130.49731 (19)0.2070 (2)0.38044 (7)0.0635 (5)
H13A0.41840.20220.39390.095*
H13B0.51150.13550.36210.095*
H13C0.50240.27890.36160.095*
C140.75164 (18)0.12016 (16)0.36732 (6)0.0507 (4)
C150.8185 (2)0.0796 (2)0.28902 (6)0.0586 (5)
C160.9248 (3)0.0025 (4)0.30166 (10)0.1008 (11)
H16C0.9005−0.05850.32340.151*
H16D0.98630.05340.31490.151*
H16A0.9560−0.03680.27480.151*
C170.8512 (4)0.1665 (3)0.25068 (9)0.0955 (10)
H17A0.91440.22050.26070.143*
H17B0.78160.21390.24230.143*
H17C0.87830.12040.22470.143*
C180.7086 (3)0.0050 (4)0.27656 (11)0.1025 (11)
H18A0.6868−0.04650.30190.154*
H18B0.7264−0.04500.25040.154*
H18C0.64280.05900.26950.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1084 (6)0.0928 (5)0.0821 (4)−0.0154 (4)−0.0342 (4)−0.0178 (4)
O10.0460 (7)0.0958 (11)0.0648 (9)0.0202 (7)−0.0022 (6)−0.0154 (8)
O20.1255 (15)0.0446 (8)0.0653 (9)0.0057 (8)0.0129 (9)0.0027 (7)
O30.0694 (8)0.0495 (7)0.0446 (6)0.0010 (6)0.0015 (6)−0.0036 (5)
N10.0414 (7)0.0721 (10)0.0481 (8)0.0038 (7)0.0036 (6)−0.0087 (7)
C10.0474 (8)0.0557 (10)0.0443 (8)0.0047 (7)0.0002 (6)−0.0028 (7)
C20.0743 (13)0.0642 (12)0.0499 (10)−0.0136 (10)0.0051 (9)0.0020 (9)
C30.0743 (13)0.0604 (12)0.0700 (12)−0.0195 (11)−0.0015 (10)0.0011 (10)
C40.0714 (12)0.0577 (11)0.0571 (10)0.0041 (9)−0.0161 (9)−0.0065 (9)
C50.0642 (11)0.0887 (15)0.0447 (9)0.0067 (11)−0.0011 (8)−0.0058 (10)
C60.0470 (9)0.0802 (13)0.0479 (9)0.0015 (9)0.0032 (7)−0.0037 (9)
C70.0413 (8)0.0528 (9)0.0399 (7)−0.0010 (7)0.0017 (6)0.0020 (7)
C80.0364 (7)0.0677 (11)0.0480 (8)0.0020 (7)−0.0013 (6)−0.0027 (8)
C90.0441 (8)0.0538 (10)0.0489 (9)−0.0056 (7)−0.0048 (7)0.0038 (7)
C100.0476 (8)0.0448 (8)0.0418 (8)−0.0005 (6)−0.0001 (6)0.0007 (7)
C110.0383 (7)0.0561 (9)0.0471 (8)0.0006 (7)0.0020 (6)0.0001 (7)
C120.0378 (7)0.0630 (10)0.0445 (8)0.0029 (7)−0.0034 (6)−0.0022 (7)
C130.0538 (10)0.0735 (13)0.0633 (11)−0.0086 (9)−0.0151 (9)−0.0045 (10)
C140.0575 (9)0.0469 (9)0.0478 (9)0.0033 (8)−0.0038 (7)−0.0005 (7)
C150.0693 (11)0.0613 (11)0.0451 (9)0.0034 (9)−0.0008 (8)−0.0103 (8)
C160.102 (2)0.126 (3)0.0742 (16)0.051 (2)0.0111 (15)−0.0059 (17)
C170.147 (3)0.0849 (17)0.0544 (13)−0.0033 (19)0.0192 (16)−0.0025 (12)
C180.102 (2)0.125 (3)0.0800 (17)−0.0311 (19)0.0000 (15)−0.0427 (18)
Geometric parameters (Å, º) top
Cl1—C41.742 (2)C9—C131.529 (2)
O1—C111.235 (2)C9—C101.537 (2)
O2—C141.193 (3)C9—H90.9800
O3—C141.332 (2)C10—C141.514 (2)
O3—C151.475 (2)C10—C111.528 (2)
N1—C71.353 (2)C10—H10A0.9800
N1—C11.414 (2)C11—C121.421 (2)
N1—H10.8600C12—H120.9300
C1—C21.383 (3)C13—H13A0.9600
C1—C61.388 (3)C13—H13B0.9600
C2—C31.383 (3)C13—H13C0.9600
C2—H20.9300C15—C161.494 (3)
C3—C41.379 (3)C15—C181.509 (3)
C3—H30.9300C15—C171.512 (3)
C4—C51.373 (3)C16—H16C0.9600
C5—C61.373 (3)C16—H16D0.9600
C5—H50.9300C16—H16A0.9600
C6—H60.9300C17—H17A0.9600
C7—C121.363 (2)C17—H17B0.9600
C7—C81.502 (2)C17—H17C0.9600
C8—C91.515 (3)C18—H18A0.9600
C8—H8A0.9700C18—H18B0.9600
C8—H8B0.9700C18—H18C0.9600
C14—O3—C15121.26 (15)C11—C10—H10108.1
C7—N1—C1127.17 (15)C9—C10—H10108.1
C7—N1—H1116.4O1—C11—C12122.87 (17)
C1—N1—H1116.4O1—C11—C10119.88 (16)
C2—C1—C6119.15 (18)C12—C11—C10117.24 (15)
C2—C1—N1121.90 (17)C7—C12—C11122.28 (16)
C6—C1—N1118.77 (17)C7—C12—H12118.9
C3—C2—C1120.67 (19)C11—C12—H12118.9
C3—C2—H2119.7C9—C13—H13A109.5
C1—C2—H2119.7C9—C13—H13B109.5
C4—C3—C2119.2 (2)H13A—C13—H13B109.5
C4—C3—H3120.4C9—C13—H13C109.5
C2—C3—H3120.4H13A—C13—H13C109.5
C5—C4—C3120.60 (19)H13B—C13—H13C109.5
C5—C4—Cl1119.86 (17)O2—C14—O3125.85 (18)
C3—C4—Cl1119.54 (19)O2—C14—C10123.68 (18)
C6—C5—C4120.15 (19)O3—C14—C10110.43 (15)
C6—C5—H5119.9O3—C15—C16109.85 (18)
C4—C5—H5119.9O3—C15—C18109.42 (19)
C5—C6—C1120.22 (19)C16—C15—C18113.1 (3)
C5—C6—H6119.9O3—C15—C17103.07 (18)
C1—C6—H6119.9C16—C15—C17110.3 (2)
N1—C7—C12124.99 (16)C18—C15—C17110.6 (2)
N1—C7—C8113.84 (15)C15—C16—H16C109.5
C12—C7—C8121.18 (15)C15—C16—H16D109.5
C7—C8—C9113.86 (15)H16C—C16—H16D109.5
C7—C8—H8A108.8C15—C16—H16A109.5
C9—C8—H8A108.8H16C—C16—H16A109.5
C7—C8—H8B108.8H16D—C16—H16A109.5
C9—C8—H8B108.8C15—C17—H17A109.5
H8A—C8—H8B107.7C15—C17—H17B109.5
C8—C9—C13111.01 (16)H17A—C17—H17B109.5
C8—C9—C10108.52 (14)C15—C17—H17C109.5
C13—C9—C10112.52 (16)H17A—C17—H17C109.5
C8—C9—H9108.2H17B—C17—H17C109.5
C13—C9—H9108.2C15—C18—H18A109.5
C10—C9—H9108.2C15—C18—H18B109.5
C14—C10—C11110.08 (14)H18A—C18—H18B109.5
C14—C10—C9111.85 (15)C15—C18—H18C109.5
C11—C10—C9110.40 (14)H18A—C18—H18C109.5
C14—C10—H10108.1H18B—C18—H18C109.5
C7—N1—C1—C244.5 (3)C8—C9—C10—C1157.46 (19)
C7—N1—C1—C6−140.4 (2)C13—C9—C10—C11−179.30 (17)
C6—C1—C2—C30.8 (3)C14—C10—C11—O117.6 (2)
N1—C1—C2—C3175.9 (2)C9—C10—C11—O1141.56 (18)
C1—C2—C3—C4−1.0 (4)C14—C10—C11—C12−163.43 (16)
C2—C3—C4—C50.2 (4)C9—C10—C11—C12−39.5 (2)
C2—C3—C4—Cl1179.48 (19)N1—C7—C12—C11178.91 (18)
C3—C4—C5—C60.7 (4)C8—C7—C12—C11−1.1 (3)
Cl1—C4—C5—C6−178.60 (18)O1—C11—C12—C7−170.34 (19)
C4—C5—C6—C1−0.8 (3)C10—C11—C12—C710.7 (3)
C2—C1—C6—C50.1 (3)C15—O3—C14—O20.7 (3)
N1—C1—C6—C5−175.1 (2)C15—O3—C14—C10−177.35 (16)
C1—N1—C7—C1212.9 (3)C11—C10—C14—O270.1 (3)
C1—N1—C7—C8−167.05 (18)C9—C10—C14—O2−53.0 (3)
N1—C7—C8—C9−158.30 (16)C11—C10—C14—O3−111.80 (17)
C12—C7—C8—C921.7 (3)C9—C10—C14—O3125.08 (17)
C7—C8—C9—C13−173.31 (16)C14—O3—C15—C16−64.0 (3)
C7—C8—C9—C10−49.2 (2)C14—O3—C15—C1860.7 (3)
C8—C9—C10—C14−179.60 (14)C14—O3—C15—C17178.4 (2)
C13—C9—C10—C14−56.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.242.909 (2)135
C6—H6···O1i0.932.633.363 (2)137
C10—H10···O2ii0.982.363.255 (2)152
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC18H22ClNO3
Mr335.82
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)11.0801 (3), 10.9095 (3), 29.2474 (7)
V (Å3)3535.39 (16)
Z8
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.45 × 0.38 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.93, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections		9798, 3708, 2925
Rint0.030
(sin θ/λ)max (Å−1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.172, 1.09
No. of reflections3708
No. of parameters212
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.39, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.242.909 (2)134.8
C6—H6···O1i0.932.633.363 (2)136.6
C10—H10···O2ii0.982.363.255 (2)152.0
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y+1/2, z.
 

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