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In the title compound, C24H23ClO4, the side chain displays an extended conformation. The main secondary inter­actions involve a bifurcated hydrogen-bond system (C—H...)2O to the carbon­yl O atom. Each ring is involved in a long C—H...π inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005374/bt6609sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005374/bt6609Isup2.hkl
Contains datablock I

CCDC reference: 270230

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.116
  • Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B .. O4 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H37B .. CL .. 3.00 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C37 .. CL .. 3.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2-[Bis(4-methoxyphenyl)methyl]benzyl chloroacetate top
Crystal data top
C24H23ClO4Z = 2
Mr = 410.87F(000) = 432
Triclinic, P1Dx = 1.320 Mg m3
a = 7.6817 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6398 (6) ÅCell parameters from 8877 reflections
c = 13.4992 (8) Åθ = 2.7–30.5°
α = 108.529 (4)°µ = 0.21 mm1
β = 92.712 (4)°T = 133 K
γ = 97.109 (4)°Prism, colourless
V = 1033.67 (10) Å30.35 × 0.21 × 0.16 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
6274 independent reflections
Radiation source: fine-focus sealed tube4988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.192 pixels mm-1θmax = 30.5°, θmin = 1.6°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 1415
Tmin = 0.890, Tmax = 0.967l = 1919
22190 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.2812P]
where P = (Fo2 + 2Fc2)/3
6274 reflections(Δ/σ)max = 0.001
264 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.21 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
Cl0.08165 (5)0.36901 (3)0.78479 (2)0.03444 (10)
O10.11035 (12)0.20368 (8)0.49316 (7)0.02504 (18)
O20.08259 (15)0.41702 (9)0.60003 (7)0.0346 (2)
O30.50891 (13)0.20767 (9)0.64641 (7)0.0289 (2)
O40.62835 (13)0.32648 (10)0.00575 (7)0.0321 (2)
C10.14283 (15)0.26084 (11)0.28743 (8)0.0189 (2)
H10.09150.34630.30990.023*
C110.01109 (15)0.14686 (11)0.24512 (8)0.0187 (2)
C120.15431 (15)0.13752 (11)0.30509 (9)0.0199 (2)
C130.28469 (16)0.02543 (12)0.27056 (9)0.0238 (2)
H130.37930.01850.31230.029*
C140.27877 (17)0.07602 (13)0.17647 (10)0.0273 (3)
H140.36780.15210.15430.033*
C150.14176 (18)0.06505 (12)0.11534 (10)0.0275 (3)
H150.13830.13260.04980.033*
C160.00883 (16)0.04513 (12)0.14990 (9)0.0231 (2)
H160.08530.05100.10770.028*
C170.17387 (17)0.24519 (12)0.40609 (9)0.0238 (2)
H17A0.10430.33110.40850.029*
H17B0.29900.25790.41120.029*
C180.06852 (16)0.30155 (12)0.58486 (9)0.0233 (2)
C190.00495 (19)0.24264 (13)0.66594 (10)0.0281 (3)
H19A0.08720.18710.63790.034*
H19B0.10430.18380.67990.034*
C210.23792 (15)0.24888 (11)0.38522 (8)0.0187 (2)
C220.25989 (15)0.12410 (11)0.39381 (9)0.0204 (2)
H220.21260.04500.33810.024*
C230.34881 (16)0.11304 (11)0.48156 (9)0.0220 (2)
H230.36090.02710.48590.026*
C240.42067 (15)0.22829 (11)0.56358 (9)0.0211 (2)
C250.39875 (16)0.35365 (11)0.55750 (9)0.0232 (2)
H250.44560.43260.61350.028*
C260.30761 (16)0.36249 (11)0.46867 (9)0.0216 (2)
H260.29280.44830.46510.026*
C270.56593 (18)0.32359 (14)0.73605 (10)0.0315 (3)
H27A0.65110.38610.71650.038*
H27B0.62160.29670.79150.038*
H27C0.46420.36740.76160.038*
C310.27152 (15)0.27217 (11)0.20694 (8)0.0196 (2)
C320.41475 (18)0.20277 (14)0.19131 (11)0.0300 (3)
H320.43060.14390.23000.036*
C330.53624 (18)0.21674 (15)0.12050 (11)0.0309 (3)
H330.63300.16780.11120.037*
C340.51402 (16)0.30270 (12)0.06400 (9)0.0236 (2)
C350.36937 (17)0.37120 (12)0.07620 (9)0.0243 (2)
H350.35230.42850.03630.029*
C360.24988 (16)0.35540 (11)0.14708 (9)0.0214 (2)
H360.15130.40240.15490.026*
C370.7768 (2)0.2573 (2)0.01895 (15)0.0541 (5)
H37A0.84520.27900.04900.065*
H37B0.85070.28480.06780.065*
H37C0.73690.16060.04710.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0371 (2)0.03979 (18)0.02513 (15)0.01096 (14)0.00302 (12)0.00685 (13)
O10.0350 (5)0.0207 (4)0.0206 (4)0.0060 (3)0.0071 (3)0.0071 (3)
O20.0529 (7)0.0231 (4)0.0283 (5)0.0150 (4)0.0050 (4)0.0054 (4)
O30.0333 (5)0.0314 (5)0.0209 (4)0.0008 (4)0.0044 (3)0.0101 (3)
O40.0278 (5)0.0461 (6)0.0290 (5)0.0038 (4)0.0086 (4)0.0211 (4)
C10.0193 (5)0.0182 (5)0.0199 (5)0.0042 (4)0.0038 (4)0.0065 (4)
C110.0182 (5)0.0192 (5)0.0197 (5)0.0045 (4)0.0020 (4)0.0070 (4)
C120.0196 (5)0.0217 (5)0.0203 (5)0.0064 (4)0.0031 (4)0.0081 (4)
C130.0194 (6)0.0288 (6)0.0267 (6)0.0041 (4)0.0041 (4)0.0131 (5)
C140.0254 (6)0.0263 (6)0.0284 (6)0.0020 (4)0.0026 (5)0.0092 (5)
C150.0299 (7)0.0254 (6)0.0225 (5)0.0012 (5)0.0004 (4)0.0027 (4)
C160.0232 (6)0.0241 (5)0.0208 (5)0.0034 (4)0.0045 (4)0.0054 (4)
C170.0275 (6)0.0242 (5)0.0228 (5)0.0096 (4)0.0082 (4)0.0091 (4)
C180.0245 (6)0.0235 (5)0.0231 (5)0.0068 (4)0.0096 (4)0.0071 (4)
C190.0358 (7)0.0263 (6)0.0243 (6)0.0095 (5)0.0075 (5)0.0089 (5)
C210.0180 (5)0.0186 (5)0.0195 (5)0.0026 (4)0.0035 (4)0.0058 (4)
C220.0228 (6)0.0164 (5)0.0202 (5)0.0018 (4)0.0009 (4)0.0041 (4)
C230.0232 (6)0.0194 (5)0.0240 (5)0.0029 (4)0.0017 (4)0.0078 (4)
C240.0194 (6)0.0251 (5)0.0189 (5)0.0013 (4)0.0023 (4)0.0081 (4)
C250.0255 (6)0.0201 (5)0.0198 (5)0.0013 (4)0.0025 (4)0.0026 (4)
C260.0248 (6)0.0163 (5)0.0228 (5)0.0018 (4)0.0038 (4)0.0052 (4)
C270.0276 (7)0.0428 (7)0.0194 (5)0.0010 (5)0.0001 (4)0.0059 (5)
C310.0199 (5)0.0187 (5)0.0200 (5)0.0018 (4)0.0020 (4)0.0066 (4)
C320.0285 (7)0.0399 (7)0.0343 (6)0.0144 (5)0.0116 (5)0.0250 (6)
C330.0245 (7)0.0451 (7)0.0341 (7)0.0146 (5)0.0109 (5)0.0234 (6)
C340.0211 (6)0.0296 (6)0.0201 (5)0.0010 (4)0.0016 (4)0.0099 (4)
C350.0302 (7)0.0225 (5)0.0220 (5)0.0020 (4)0.0012 (4)0.0106 (4)
C360.0244 (6)0.0180 (5)0.0214 (5)0.0043 (4)0.0008 (4)0.0059 (4)
C370.0299 (8)0.1039 (15)0.0518 (10)0.0221 (9)0.0191 (7)0.0513 (11)
Geometric parameters (Å, º) top
Cl—C191.7695 (13)C32—C331.3953 (17)
O1—C181.3343 (14)C33—C341.3846 (17)
O1—C171.4641 (14)C34—C351.3908 (18)
O2—C181.1991 (15)C35—C361.3905 (17)
O3—C241.3706 (14)C1—H11.0000
O3—C271.4300 (15)C13—H130.9500
O4—C341.3772 (14)C14—H140.9500
O4—C371.4201 (19)C15—H150.9500
C1—C311.5257 (15)C16—H160.9500
C1—C211.5267 (15)C17—H17A0.9900
C1—C111.5284 (15)C17—H17B0.9900
C11—C161.3952 (15)C19—H19A0.9900
C11—C121.4086 (15)C19—H19B0.9900
C12—C131.3963 (16)C22—H220.9500
C12—C171.5043 (15)C23—H230.9500
C13—C141.3880 (17)C25—H250.9500
C14—C151.3839 (18)C26—H260.9500
C15—C161.3949 (17)C27—H27A0.9800
C18—C191.5134 (17)C27—H27B0.9800
C21—C261.3907 (15)C27—H27C0.9800
C21—C221.3986 (15)C32—H320.9500
C22—C231.3840 (16)C33—H330.9500
C23—C241.3950 (16)C35—H350.9500
C24—C251.3922 (16)C36—H360.9500
C25—C261.3948 (17)C37—H37A0.9800
C31—C321.3872 (16)C37—H37B0.9800
C31—C361.3941 (15)C37—H37C0.9800
C18—O1—C17115.63 (9)C12—C13—H13119.4
C24—O3—C27116.41 (10)C15—C14—H14120.4
C34—O4—C37116.74 (11)C13—C14—H14120.4
C31—C1—C21111.18 (9)C14—C15—H15120.0
C31—C1—C11114.30 (9)C16—C15—H15120.0
C21—C1—C11109.87 (9)C15—C16—H16119.3
C16—C11—C12118.21 (10)C11—C16—H16119.3
C16—C11—C1121.28 (10)O1—C17—H17A110.1
C12—C11—C1120.38 (9)C12—C17—H17A110.1
C13—C12—C11119.70 (10)O1—C17—H17B110.1
C13—C12—C17117.93 (10)C12—C17—H17B110.1
C11—C12—C17122.37 (10)H17A—C17—H17B108.4
C14—C13—C12121.28 (11)C18—C19—H19A109.3
C15—C14—C13119.27 (11)Cl—C19—H19A109.3
C14—C15—C16120.02 (11)C18—C19—H19B109.3
C15—C16—C11121.45 (11)Cl—C19—H19B109.3
O1—C17—C12108.15 (9)H19A—C19—H19B107.9
O2—C18—O1124.89 (12)C23—C22—H22119.2
O2—C18—C19126.01 (11)C21—C22—H22119.2
O1—C18—C19109.08 (10)C22—C23—H23120.1
C18—C19—Cl111.67 (9)C24—C23—H23120.1
C26—C21—C22117.64 (10)C24—C25—H25120.2
C26—C21—C1120.87 (9)C26—C25—H25120.2
C22—C21—C1121.48 (10)C21—C26—H26119.2
C23—C22—C21121.61 (10)C25—C26—H26119.2
C22—C23—C24119.88 (10)O3—C27—H27A109.5
O3—C24—C25124.59 (10)O3—C27—H27B109.5
O3—C24—C23115.80 (10)H27A—C27—H27B109.5
C25—C24—C23119.61 (10)O3—C27—H27C109.5
C24—C25—C26119.56 (10)H27A—C27—H27C109.5
C21—C26—C25121.68 (10)H27B—C27—H27C109.5
C32—C31—C36117.46 (10)C31—C32—H32118.9
C32—C31—C1122.00 (10)C33—C32—H32118.9
C36—C31—C1120.53 (10)C34—C33—H33120.4
C31—C32—C33122.11 (11)C32—C33—H33120.4
C34—C33—C32119.21 (12)C36—C35—H35120.1
O4—C34—C33123.94 (11)C34—C35—H35120.1
O4—C34—C35116.09 (11)C35—C36—H36119.3
C33—C34—C35119.97 (11)C31—C36—H36119.3
C36—C35—C34119.74 (11)O4—C37—H37A109.5
C35—C36—C31121.48 (11)O4—C37—H37B109.5
C31—C1—H1107.0H37A—C37—H37B109.5
C21—C1—H1107.0O4—C37—H37C109.5
C11—C1—H1107.0H37A—C37—H37C109.5
C14—C13—H13119.4H37B—C37—H37C109.5
C31—C1—C11—C1614.29 (15)C27—O3—C24—C256.43 (17)
C21—C1—C11—C16111.49 (11)C27—O3—C24—C23173.14 (10)
C31—C1—C11—C12169.84 (10)C22—C23—C24—O3178.93 (11)
C21—C1—C11—C1264.39 (13)C22—C23—C24—C251.47 (17)
C16—C11—C12—C132.77 (16)O3—C24—C25—C26179.41 (11)
C1—C11—C12—C13173.23 (10)C23—C24—C25—C261.03 (17)
C16—C11—C12—C17176.85 (10)C22—C21—C26—C250.95 (17)
C1—C11—C12—C177.15 (16)C1—C21—C26—C25178.36 (10)
C11—C12—C13—C141.73 (17)C24—C25—C26—C210.20 (18)
C17—C12—C13—C14177.91 (11)C21—C1—C31—C3236.38 (15)
C12—C13—C14—C150.62 (18)C11—C1—C31—C3288.70 (14)
C13—C14—C15—C161.87 (19)C21—C1—C31—C36142.65 (10)
C14—C15—C16—C110.77 (19)C11—C1—C31—C3692.27 (12)
C12—C11—C16—C151.56 (17)C36—C31—C32—C331.5 (2)
C1—C11—C16—C15174.40 (11)C1—C31—C32—C33177.60 (12)
C18—O1—C17—C12160.60 (10)C31—C32—C33—C340.2 (2)
C13—C12—C17—O181.55 (13)C37—O4—C34—C330.0 (2)
C11—C12—C17—O198.82 (12)C37—O4—C34—C35179.94 (14)
C17—O1—C18—O21.44 (18)C32—C33—C34—O4178.28 (12)
C17—O1—C18—C19179.76 (10)C32—C33—C34—C351.7 (2)
O2—C18—C19—Cl9.37 (17)O4—C34—C35—C36178.41 (10)
O1—C18—C19—Cl171.84 (8)C33—C34—C35—C361.54 (18)
C31—C1—C21—C2688.73 (12)C34—C35—C36—C310.12 (18)
C11—C1—C21—C26143.74 (10)C32—C31—C36—C351.58 (17)
C31—C1—C21—C2290.55 (12)C1—C31—C36—C35177.49 (10)
C11—C1—C21—C2236.98 (14)H1—C1—C11—C1251.5
C26—C21—C22—C230.49 (17)H1—C1—C21—C2627.9
C1—C21—C22—C23178.81 (10)H1—C1—C31—C3626.1
C21—C22—C23—C240.71 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i1.002.433.3793 (14)157
C26—H26···O2i0.952.583.4039 (15)145
C27—H27B···O4ii0.982.653.4856 (16)143
C37—H37B···Cliii0.983.003.9767 (16)179
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x+1, y, z1.
 

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