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Crown ethers and their supra­molecular derivatives are well-known chelators and scavengers for a variety of cations, most notably heavier alkali and alkaline-earth ions. Although they are widely used in synthetic chemistry, available crystal structures of uncoordinated and solvent-free crown ethers regularly suffer from disorder. In this study, we present the X-ray crystal structure analysis of well-ordered solvent-free crystals of dibenzo-21-crown-7 (systematic name: dibenzo[b,k]-1,4,7,10,13,16,19-hepta­oxa­cyclo­heneicosa-2,11-diene, C22H28O7). Because of the quality of the crystal and diffraction data, we have chosen invarioms, in addition to standard independent spherical atoms, for modelling and briefly discuss the different refinement results. The electrostatic potential, which is directly deducible from the invariom model, and the Hirshfeld surface are analysed and complemented with inter­action-energy computations to characterize inter­molecular contacts. The boat-like mol­ecules stack along the a axis and are arranged as dimers of chains, which assemble as rows to form a three-dimensional structure. Dispersive C—H...H—C and C—H...π inter­actions dominate, but nonclassical hydrogen bonds are present and reflect the overall rather weak electrostatic influence. A fingerprint plot of the Hirshfeld surface summarizes and visualizes the inter­molecular inter­actions. The insight gained into the crystal structure of dibenzo-21-crown-7 not only demonstrates the power of invariom refinement, Hirshfeld surface analysis and inter­action-energy computation, but also hints at favourable conditions for crystallizing solvent-free crown ethers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011160/sk3663sup1.cif
Contains datablocks global, Invariom, IAM

mol

MDL mol file https://doi.org/10.1107/S2053229617011160/sk3663Invariomsup2.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011160/sk3663IAMsup3.hkl
Contains datablock IAM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011160/sk3663Invariomsup4.hkl
Contains datablock Invariom

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617011160/sk3663sup5.pdf
Invariom information, interaction energies and additional figures

CCDC references: 1565414; 1565413

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: XD2016 (Volkov et al., 2016) for Invariom; SHELXL2016 (Sheldrick, 2015b) for IAM. For both structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008). Software used to prepare material for publication: WinXD (Volkov et al., 2016) for Invariom; OLEX2 (Dolomanov et al., 2009) for IAM.

Dibenzo[b,k][1,4,7,10,13,16,19]heptaoxacyclohenicosa-2,11-diene (Invariom) top
Crystal data top
C22H28O7Dx = 1.34 Mg m3
Mr = 404.44Melting point: 388 K
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 4.9801 (1) ÅCell parameters from 7438 reflections
b = 17.4771 (2) Åθ = 2.5–73.5°
c = 23.1000 (2) ŵ = 0.82 mm1
β = 94.124 (1)°T = 150 K
V = 2005.37 (5) Å3Shard, colourless
Z = 40.74 × 0.14 × 0.08 mm
F(000) = 864
Data collection top
Agilent SuperNova (single source)
diffractometer
3925 independent reflections
Radiation source: micro-focus sealed tube, Agilent Nova3559 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.018
Detector resolution: 10.5435 pixels mm-1θmax = 73.7°, θmin = 3.2°
ω scansh = 56
Absorption correction: gaussian
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
k = 2121
Tmin = 0.598, Tmax = 1.000l = 2728
13236 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Only H-atom displacement parameters refined
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3664 reflectionsΔρmax = 0.41 e Å3
290 parametersΔρmin = 0.24 e Å3
0 restraints
Special details top

Refinement. After conventional IAM refinement, invarioms were assigned and set up using MoleCoolQt Revision 558 (Hübschle & Dittrich, 2011).

All hydrogen atoms were reset to neutron-diffraction–derived distances to their carrier atoms after every refinement cycle (d = 1.0962 Å for methylene groups, d = 1.0823 Å for aromatics).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C21.0446 (2)0.65479 (6)0.55315 (5)0.027
H2A1.155150.704080.5376430.056 (5)*
H2B0.9218450.6739820.5879140.051 (4)*
C30.8678 (2)0.61989 (6)0.50382 (5)0.026
H3A0.991840.5978680.4702030.040 (4)*
H3B0.7492370.5725870.5199140.042 (4)*
C50.5121 (2)0.66085 (6)0.43710 (4)0.024
C60.4908 (2)0.58977 (6)0.41032 (5)0.027
H60.6285610.5442070.4238520.043 (4)*
C70.2899 (2)0.57697 (7)0.36562 (5)0.03
H70.2752950.521870.3442380.053 (4)*
C80.1099 (2)0.63436 (7)0.34872 (5)0.031
H80.0467290.6237250.3147260.057 (5)*
C90.1296 (2)0.70607 (6)0.37537 (5)0.028
H90.0118150.7508580.3621140.051 (4)*
C100.3311 (2)0.71984 (6)0.41890 (4)0.024
C120.1553 (2)0.84115 (7)0.44408 (5)0.033
H12A0.0232160.8147770.4608370.061 (5)*
H12B0.1041540.8592910.3992120.060 (5)*
C130.2414 (3)0.90954 (7)0.48096 (5)0.037
H13A0.4247680.9332290.464390.064 (5)*
H13B0.084290.9533820.4753370.064 (5)*
C150.5459 (3)0.85914 (8)0.55510 (6)0.041
H15A0.694610.8804860.5262820.075 (6)*
H15B0.5281370.7970780.5491150.081 (6)*
C160.6417 (3)0.87561 (8)0.61654 (6)0.04
H16A0.8540310.8593330.6238210.092 (7)*
H16B0.6244330.9370830.6249370.075 (6)*
C180.5696 (3)0.84899 (7)0.71319 (6)0.039
H18A0.4507590.8960870.7294980.069 (6)*
H18B0.7818930.8661090.7164920.066 (5)*
C190.5354 (2)0.77896 (6)0.74960 (5)0.032
H19A0.5615020.7934970.7958240.054 (4)*
H19B0.333720.7547760.7404260.057 (5)*
C210.7616 (2)0.66022 (6)0.76552 (5)0.026
C220.6192 (2)0.64273 (6)0.81330 (5)0.03
H220.4763840.6834090.8285430.054 (4)*
C230.6593 (2)0.57272 (7)0.84169 (5)0.034
H230.5475140.5593740.878880.059 (5)*
C240.8413 (2)0.52029 (7)0.82286 (5)0.034
H240.8717980.4662270.8452150.050 (4)*
C250.9859 (2)0.53724 (6)0.77468 (5)0.03
H251.1294050.4963120.7600650.055 (4)*
C260.9465 (2)0.60623 (6)0.74558 (5)0.026
C281.2705 (2)0.57778 (6)0.67776 (5)0.026
H28A1.1828080.5218460.6661160.045 (4)*
H28B1.4322270.5694030.7119380.043 (4)*
C291.3829 (2)0.61374 (7)0.62490 (5)0.029
H29A1.3910050.6759460.6308390.051 (4)*
H29B1.5890780.593290.6212680.054 (5)*
O11.22374 (18)0.59660 (5)0.57328 (4)0.037
O40.69566 (15)0.67931 (4)0.48120 (3)0.028
O110.37270 (15)0.78813 (4)0.44647 (3)0.03
O140.29216 (18)0.89459 (5)0.54075 (4)0.04
O170.48593 (19)0.83406 (5)0.65485 (4)0.041
O200.73637 (16)0.72575 (4)0.73461 (4)0.033
O271.06943 (15)0.62756 (5)0.69748 (3)0.031
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0249 (5)0.0283 (5)0.0278 (5)0.0033 (4)0.0007 (4)0.0021 (4)
C30.0234 (5)0.0272 (5)0.0270 (5)0.0028 (4)0.0005 (4)0.0013 (4)
C50.0203 (5)0.0241 (5)0.0262 (5)0.0025 (4)0.0008 (4)0.0020 (4)
C60.0228 (5)0.0246 (5)0.0330 (6)0.0032 (4)0.0010 (4)0.0055 (4)
C70.0264 (6)0.0293 (6)0.0342 (6)0.0012 (4)0.0033 (4)0.0068 (4)
C80.0272 (6)0.0326 (6)0.0313 (6)0.0014 (4)0.0051 (4)0.0021 (5)
C90.0264 (5)0.0289 (6)0.0294 (5)0.0031 (4)0.0027 (4)0.0018 (4)
C100.0237 (5)0.0234 (5)0.0259 (5)0.0038 (4)0.0013 (4)0.0006 (4)
C120.0358 (6)0.0281 (6)0.0340 (6)0.0106 (5)0.0025 (5)0.0001 (5)
C130.0508 (8)0.0278 (6)0.0342 (6)0.0113 (5)0.0060 (5)0.0023 (5)
C150.0394 (7)0.0482 (8)0.0350 (7)0.0064 (6)0.0050 (5)0.0052 (6)
C160.0397 (7)0.0396 (7)0.0394 (7)0.0005 (5)0.0035 (5)0.0083 (5)
C180.0516 (8)0.0280 (6)0.0361 (6)0.0036 (5)0.0010 (5)0.0021 (5)
C190.0353 (6)0.0281 (6)0.0319 (6)0.0056 (5)0.0031 (5)0.0034 (4)
C210.0246 (5)0.0245 (5)0.0282 (5)0.0006 (4)0.0025 (4)0.0054 (4)
C220.0311 (6)0.0280 (5)0.0315 (6)0.0019 (4)0.0058 (4)0.0041 (4)
C230.0366 (6)0.0314 (6)0.0339 (6)0.0043 (5)0.0063 (5)0.0006 (5)
C240.0345 (6)0.0286 (6)0.0384 (6)0.0022 (5)0.0023 (5)0.0029 (5)
C250.0272 (6)0.0269 (6)0.0362 (6)0.0006 (4)0.0005 (4)0.0007 (5)
C260.0216 (5)0.0255 (5)0.0300 (5)0.0006 (4)0.0001 (4)0.0042 (4)
C280.0200 (5)0.0287 (5)0.0303 (5)0.0027 (4)0.0011 (4)0.0049 (4)
C290.0244 (5)0.0330 (6)0.0293 (5)0.0034 (4)0.0004 (4)0.0023 (4)
O10.0432 (5)0.0342 (4)0.0319 (4)0.0131 (4)0.0102 (4)0.0083 (3)
O40.0251 (4)0.0261 (4)0.0311 (4)0.0045 (3)0.0034 (3)0.0041 (3)
O110.0291 (4)0.0252 (4)0.0343 (4)0.0055 (3)0.0003 (3)0.0034 (3)
O140.0411 (5)0.0465 (5)0.0322 (4)0.0101 (4)0.0081 (4)0.0028 (4)
O170.0489 (5)0.0393 (5)0.0349 (5)0.0029 (4)0.0011 (4)0.0011 (4)
O200.0358 (4)0.0283 (4)0.0353 (4)0.0053 (3)0.0093 (3)0.0001 (3)
O270.0284 (4)0.0310 (4)0.0332 (4)0.0059 (3)0.0055 (3)0.0004 (3)
Geometric parameters (Å, º) top
C2—H2A1.0962C16—H16A1.0962
C2—H2B1.0962C16—H16B1.0963
C2—C31.5171 (15)C16—O171.4181 (16)
C2—O11.4095 (13)C18—H18A1.0962
C3—H3A1.0963C18—H18B1.0962
C3—H3B1.0963C18—C191.5015 (17)
C3—O41.4221 (12)C18—O171.4060 (15)
C5—C61.3885 (15)C19—H19A1.0962
C5—C101.4135 (14)C19—H19B1.0962
C5—O41.3577 (12)C19—O201.4270 (13)
C6—H61.0822C21—C221.3882 (15)
C6—C71.4033 (15)C21—C261.4184 (14)
C7—H71.0822C21—O201.3507 (13)
C7—C81.3827 (16)C22—H221.0822
C8—H81.0823C22—C231.3957 (17)
C8—C91.3966 (16)C23—H231.0823
C9—H91.0822C23—C241.3810 (17)
C9—C101.3896 (15)C24—H241.0823
C10—O111.3618 (13)C24—C251.3999 (17)
C12—H12A1.0963C25—H251.0823
C12—H12B1.0962C25—C261.3875 (16)
C12—C131.5120 (17)C26—O271.3589 (13)
C12—O111.4232 (13)C28—H28A1.0963
C13—H13A1.0962C28—H28B1.0962
C13—H13B1.0962C28—C291.5157 (16)
C13—O141.4105 (15)C28—O271.4258 (12)
C15—H15A1.0963C29—H29A1.0963
C15—H15B1.0962C29—H29B1.0962
C15—C161.4924 (18)C29—O11.4155 (13)
C15—O141.4248 (16)
H2A—C2—H2B108.58H16A—C16—O17109.65
H2A—C2—C3110.40H16B—C16—O17109.76
H2A—C2—O1110.73H18A—C18—H18B108.23
H2B—C2—C3110.43H18A—C18—C19109.50
H2B—C2—O1110.62H18A—C18—O17109.79
C3—C2—O1106.08 (8)H18B—C18—C19109.34
C2—C3—H3A110.31H18B—C18—O17109.58
C2—C3—H3B110.26C19—C18—O17110.36 (10)
C2—C3—O4106.52 (8)C18—C19—H19A110.27
H3A—C3—H3B108.67C18—C19—H19B110.20
H3A—C3—O4110.58C18—C19—O20106.59 (9)
H3B—C3—O4110.49H19A—C19—H19B108.69
C6—C5—C10119.56 (10)H19A—C19—O20110.56
C6—C5—O4124.93 (9)H19B—C19—O20110.53
C10—C5—O4115.50 (9)C22—C21—C26119.50 (10)
C5—C6—H6120.20C22—C21—O20125.01 (10)
C5—C6—C7119.87 (10)C26—C21—O20115.49 (9)
H6—C6—C7119.93C21—C22—H22119.95
C6—C7—H7119.90C21—C22—C23120.17 (10)
C6—C7—C8120.38 (10)H22—C22—C23119.88
H7—C7—C8119.72C22—C23—H23119.83
C7—C8—H8119.93C22—C23—C24120.58 (11)
C7—C8—C9120.20 (10)H23—C23—C24119.59
H8—C8—C9119.87C23—C24—H24120.11
C8—C9—H9120.05C23—C24—C25119.78 (11)
C8—C9—C10119.90 (10)H24—C24—C25120.10
H9—C9—C10120.05C24—C25—H25119.81
C5—C10—C9120.06 (10)C24—C25—C26120.41 (11)
C5—C10—O11115.32 (9)H25—C25—C26119.78
C9—C10—O11124.61 (9)C21—C26—C25119.56 (10)
H12A—C12—H12B108.44C21—C26—O27115.11 (9)
H12A—C12—C13109.75C25—C26—O27125.33 (10)
H12A—C12—O11110.28H28A—C28—H28B108.47
H12B—C12—C13109.95H28A—C28—C29109.61
H12B—C12—O11110.44H28A—C28—O27110.23
C13—C12—O11107.97 (10)H28B—C28—C29109.93
C12—C13—H13A108.15H28B—C28—O27110.36
C12—C13—H13B108.33C29—C28—O27108.23 (9)
C12—C13—O14115.39 (10)C28—C29—H29A108.84
H13A—C13—H13B107.46C28—C29—H29B109.19
H13A—C13—O14108.47C28—C29—O1111.98 (9)
H13B—C13—O14108.76H29A—C29—H29B107.85
H15A—C15—H15B108.18H29A—C29—O1109.19
H15A—C15—C16109.15H29B—C29—O1109.72
H15A—C15—O14109.71C2—O1—C29115.34 (8)
H15B—C15—C16109.15C3—O4—C5117.24 (8)
H15B—C15—O14109.80C10—O11—C12117.56 (8)
C16—C15—O14110.79 (10)C13—O14—C15113.69 (9)
C15—C16—H16A109.56C16—O17—C18111.43 (10)
C15—C16—H16B109.48C19—O20—C21117.68 (9)
C15—C16—O17110.05 (11)C26—O27—C28117.51 (9)
H16A—C16—H16B108.31
H2A—C2—C3—H3A63.05C16—C15—O14—C13154.91 (14)
H2A—C2—C3—H3B176.92O14—C15—C16—H16A167.24
H2A—C2—C3—O457.00O14—C15—C16—H16B48.60
H2A—C2—O1—C2968.75O14—C15—C16—O1772.12 (12)
H2B—C2—C3—H3A176.87C15—C16—O17—C18179.38 (14)
H2B—C2—C3—H3B56.83H16A—C16—O17—C1860.04 (11)
H2B—C2—C3—O463.08H16B—C16—O17—C1858.83
H2B—C2—O1—C2951.67H18A—C18—C19—H19A47.69
O1—C2—C3—H3A56.97H18A—C18—C19—H19B72.30
O1—C2—C3—H3B63.07H18A—C18—C19—O20167.74
C3—C2—O1—C29171.45 (12)H18A—C18—O17—C1692.57
O1—C2—C3—O4177.02 (11)H18B—C18—C19—H19A70.74
C2—C3—O4—C5178.27 (12)H18B—C18—C19—H19B169.27
H3A—C3—O4—C561.85H18B—C18—C19—O2049.31
H3B—C3—O4—C558.50H18B—C18—O17—C1626.18
C10—C5—C6—H6179.91 (16)C19—C18—O17—C16146.64 (14)
C10—C5—C6—C70.19 (10)O17—C18—C19—H19A168.66
C6—C5—C10—C91.44 (10)O17—C18—C19—H19B48.67
C6—C5—C10—O11178.08 (14)O17—C18—C19—O2071.29 (11)
C6—C5—O4—C34.01 (10)C18—C19—O20—C21174.35 (13)
O4—C5—C6—H60.88H19A—C19—O20—C2154.49
O4—C5—C6—C7179.03 (16)H19B—C19—O20—C2165.90
C10—C5—O4—C3175.23 (13)C26—C21—C22—H22179.44
O4—C5—C10—C9177.85 (14)C26—C21—C22—C230.42 (10)
O4—C5—C10—O112.63 (8)C22—C21—C26—C251.08 (10)
C5—C6—C7—H7178.98C22—C21—C26—O27177.96 (15)
C5—C6—C7—C81.08 (10)C22—C21—O20—C194.50 (10)
H6—C6—C7—H71.12O20—C21—C22—H220.55
H6—C6—C7—C8178.82O20—C21—C22—C23179.31 (17)
C6—C7—C8—H8178.94C26—C21—O20—C19174.42 (14)
C6—C7—C8—C91.11 (11)O20—C21—C26—C25179.93 (15)
H7—C7—C8—H81.00O20—C21—C26—O271.03 (9)
H7—C7—C8—C9178.95C21—C22—C23—H23179.90 (18)
C7—C8—C9—H9179.89 (17)C21—C22—C23—C240.29 (11)
C7—C8—C9—C100.15 (11)H22—C22—C23—H230.04 (10)
H8—C8—C9—H90.15 (10)H22—C22—C23—C24179.85 (18)
H8—C8—C9—C10179.80 (17)C22—C23—C24—H24179.75 (18)
C8—C9—C10—C51.42 (10)C22—C23—C24—C250.35 (11)
C8—C9—C10—O11178.05 (17)H23—C23—C24—H240.05 (10)
H9—C9—C10—C5178.62H23—C23—C24—C25179.84 (18)
H9—C9—C10—O111.91C23—C24—C25—H25179.62 (18)
C5—C10—O11—C12160.57 (13)C23—C24—C25—C260.32 (11)
C9—C10—O11—C1219.94 (10)H24—C24—C25—H250.48 (10)
H12A—C12—C13—H13A177.62H24—C24—C25—C26179.58 (18)
H12A—C12—C13—H13B66.19C24—C25—C26—C211.03 (10)
H12A—C12—C13—O1455.97C24—C25—C26—O27177.91 (17)
H12A—C12—O11—C1056.09H25—C25—C26—C21178.92
H12B—C12—C13—H13A63.17H25—C25—C26—O272.15
H12B—C12—C13—H13B53.01C21—C26—O27—C28175.91 (13)
H12B—C12—C13—O14175.18C25—C26—O27—C285.11 (10)
H12B—C12—O11—C1063.75H28A—C28—C29—H29A156.43
C13—C12—O11—C10176.00 (13)H28A—C28—C29—H29B86.08
O11—C12—C13—H13A57.38H28A—C28—C29—O135.63
O11—C12—C13—H13B173.57H28A—C28—O27—C2661.37
O11—C12—C13—O1464.27 (11)H28B—C28—C29—H29A84.43
C12—C13—O14—C1577.86 (12)H28B—C28—C29—H29B33.06
H13A—C13—O14—C1543.62H28B—C28—C29—O1154.77
H13B—C13—O14—C15160.21H28B—C28—O27—C2658.42
H15A—C15—C16—H16A46.32C29—C28—O27—C26178.76 (12)
H15A—C15—C16—H16B72.32O27—C28—C29—H29A36.17
H15A—C15—C16—O17166.96O27—C28—C29—H29B153.66
H15A—C15—O14—C1334.32O27—C28—C29—O184.63 (10)
H15B—C15—C16—H16A71.73C28—C29—O1—C299.84 (11)
H15B—C15—C16—H16B169.63H29A—C29—O1—C220.76
H15B—C15—C16—O1748.91H29B—C29—O1—C2138.75
H15B—C15—O14—C1384.44
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O11i1.102.853.8410 (14)151
C6—H6···O1ii1.082.573.5631 (13)153
C7—H7···O27iii1.083.234.2104 (14)151
C13—H13B···O14iv1.103.264.3405 (15)170
C16—H16A···O17i1.103.214.2956 (16)172
C19—H19B···O20v1.103.014.0769 (14)164
C29—H29A···O17i1.102.853.9393 (15)172
C29—H29B···O1i1.103.424.4459 (14)156
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x, y+2, z+1; (v) x1, y, z.
Dibenzo[b,k][1,4,7,10,13,16,19]heptaoxacyclohenicosa-2,11-diene (IAM) top
Crystal data top
C22H28O7Dx = 1.340 Mg m3
Mr = 404.44Melting point: 388 K
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 4.9801 (1) ÅCell parameters from 7438 reflections
b = 17.4771 (2) Åθ = 2.5–73.5°
c = 23.1000 (2) ŵ = 0.82 mm1
β = 94.124 (1)°T = 150 K
V = 2005.37 (5) Å3Shard, colourless
Z = 40.74 × 0.14 × 0.08 mm
F(000) = 864
Data collection top
Agilent SuperNova (Single Source)
diffractometer
3925 independent reflections
Radiation source: micro-focus sealed tube, Agilent Nova3559 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.018
Detector resolution: 10.5435 pixels mm-1θmax = 73.7°, θmin = 3.2°
ω scansh = 56
Absorption correction: gaussian
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
k = 2121
Tmin = 0.598, Tmax = 1.000l = 2728
13236 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.7337P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3925 reflectionsΔρmax = 0.39 e Å3
262 parametersΔρmin = 0.28 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All hydrogen atoms were refined with standard riding models (d = 0.99 Å for methylene groups, d = 0.95 Å for aromatics) and Uiso(H) = 1.2 × Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C21.0441 (3)0.65491 (8)0.55310 (6)0.0297 (3)
H2A1.1444730.6993490.5391260.036*
H2B0.9335910.6721470.5845720.036*
C30.8681 (3)0.61985 (7)0.50392 (6)0.0284 (3)
H3A0.9797830.6000090.4734890.034*
H3B0.7607090.5771460.5183690.034*
C50.5116 (2)0.66076 (7)0.43693 (5)0.0263 (3)
C60.4900 (3)0.58992 (8)0.41022 (6)0.0296 (3)
H60.6110550.5499790.4221260.036*
C70.2897 (3)0.57723 (8)0.36571 (6)0.0330 (3)
H70.2771190.5288630.3469470.040*
C80.1107 (3)0.63442 (8)0.34888 (6)0.0333 (3)
H80.0267970.6250780.3190460.040*
C90.1303 (3)0.70585 (8)0.37543 (6)0.0312 (3)
H90.0061820.7451600.3638040.037*
C100.3313 (3)0.71958 (7)0.41884 (5)0.0272 (3)
C120.1548 (3)0.84138 (8)0.44420 (6)0.0354 (3)
H12A0.0061340.8173320.4592370.042*
H12B0.1091090.8575350.4036080.042*
C130.2412 (3)0.90949 (8)0.48085 (6)0.0400 (3)
H13A0.4069190.9309190.4659930.048*
H13B0.0994470.9491410.4758680.048*
C150.5467 (3)0.85913 (10)0.55533 (7)0.0431 (4)
H15A0.6801580.8784000.5291160.052*
H15B0.5299380.8031240.5497220.052*
C160.6416 (3)0.87554 (9)0.61641 (7)0.0418 (4)
H16A0.8333820.8609140.6231030.050*
H16B0.6261190.9310380.6240990.050*
C180.5696 (3)0.84884 (9)0.71328 (7)0.0413 (3)
H18A0.4623990.8914580.7279120.050*
H18B0.7612530.8644250.7161770.050*
C190.5352 (3)0.77915 (8)0.74954 (6)0.0343 (3)
H19A0.5589380.7921030.7913190.041*
H19B0.3532590.7571380.7413140.041*
C210.7615 (3)0.66002 (7)0.76567 (6)0.0284 (3)
C220.6198 (3)0.64255 (8)0.81321 (6)0.0326 (3)
H220.4944450.6782600.8266140.039*
C230.6602 (3)0.57274 (8)0.84152 (6)0.0362 (3)
H230.5618080.5610650.8741380.043*
C240.8411 (3)0.52054 (8)0.82273 (6)0.0363 (3)
H240.8679210.4731030.8423730.044*
C250.9854 (3)0.53739 (8)0.77473 (6)0.0329 (3)
H251.1114040.5014490.7619010.039*
C260.9459 (2)0.60618 (7)0.74572 (6)0.0283 (3)
C281.2710 (2)0.57773 (8)0.67757 (6)0.0290 (3)
H28A1.1913030.5272260.6672250.035*
H28B1.4164180.5702210.7085710.035*
C291.3829 (3)0.61383 (8)0.62507 (6)0.0316 (3)
H29A1.3902280.6700290.6302940.038*
H29B1.5689070.5952950.6216410.038*
O11.2240 (2)0.59634 (6)0.57316 (4)0.0395 (3)
O40.69569 (18)0.67957 (5)0.48126 (4)0.0302 (2)
O110.37362 (19)0.78814 (5)0.44656 (4)0.0323 (2)
O140.2914 (2)0.89471 (6)0.54092 (4)0.0422 (3)
O170.4851 (2)0.83391 (6)0.65474 (5)0.0439 (3)
O200.7371 (2)0.72584 (5)0.73445 (4)0.0354 (2)
O271.06917 (19)0.62778 (5)0.69739 (4)0.0331 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0276 (6)0.0300 (7)0.0313 (7)0.0043 (5)0.0006 (5)0.0009 (5)
C30.0262 (6)0.0282 (6)0.0304 (6)0.0042 (5)0.0004 (5)0.0001 (5)
C50.0219 (6)0.0304 (6)0.0266 (6)0.0000 (5)0.0025 (5)0.0008 (5)
C60.0249 (6)0.0283 (6)0.0357 (7)0.0041 (5)0.0018 (5)0.0027 (5)
C70.0302 (7)0.0320 (7)0.0365 (7)0.0008 (5)0.0008 (5)0.0068 (6)
C80.0286 (7)0.0388 (8)0.0317 (7)0.0012 (5)0.0030 (5)0.0013 (6)
C90.0282 (7)0.0329 (7)0.0321 (7)0.0039 (5)0.0001 (5)0.0042 (5)
C100.0281 (6)0.0262 (6)0.0278 (6)0.0012 (5)0.0054 (5)0.0002 (5)
C120.0371 (7)0.0312 (7)0.0378 (7)0.0121 (6)0.0031 (6)0.0015 (6)
C130.0529 (9)0.0323 (7)0.0353 (7)0.0120 (7)0.0066 (6)0.0001 (6)
C150.0406 (8)0.0492 (9)0.0399 (8)0.0075 (7)0.0060 (6)0.0043 (7)
C160.0408 (8)0.0411 (8)0.0440 (8)0.0008 (6)0.0056 (6)0.0073 (6)
C180.0532 (9)0.0323 (7)0.0377 (8)0.0043 (7)0.0015 (7)0.0036 (6)
C190.0366 (7)0.0316 (7)0.0349 (7)0.0064 (6)0.0038 (6)0.0052 (6)
C210.0273 (6)0.0262 (6)0.0313 (6)0.0026 (5)0.0014 (5)0.0049 (5)
C220.0318 (7)0.0317 (7)0.0345 (7)0.0029 (5)0.0041 (5)0.0071 (5)
C230.0376 (8)0.0368 (8)0.0344 (7)0.0071 (6)0.0046 (6)0.0021 (6)
C240.0367 (7)0.0310 (7)0.0406 (8)0.0044 (6)0.0015 (6)0.0026 (6)
C250.0278 (7)0.0304 (7)0.0400 (7)0.0003 (5)0.0013 (5)0.0034 (6)
C260.0236 (6)0.0303 (7)0.0305 (6)0.0028 (5)0.0014 (5)0.0048 (5)
C280.0218 (6)0.0309 (7)0.0338 (7)0.0037 (5)0.0015 (5)0.0061 (5)
C290.0270 (7)0.0353 (7)0.0320 (7)0.0037 (5)0.0017 (5)0.0038 (5)
O10.0458 (6)0.0367 (5)0.0338 (5)0.0139 (4)0.0116 (4)0.0084 (4)
O40.0272 (5)0.0287 (5)0.0338 (5)0.0050 (4)0.0042 (4)0.0042 (4)
O110.0319 (5)0.0267 (5)0.0378 (5)0.0061 (4)0.0005 (4)0.0043 (4)
O140.0436 (6)0.0504 (6)0.0335 (5)0.0113 (5)0.0078 (4)0.0021 (5)
O170.0525 (6)0.0431 (6)0.0355 (5)0.0040 (5)0.0007 (5)0.0012 (4)
O200.0387 (5)0.0302 (5)0.0383 (5)0.0064 (4)0.0099 (4)0.0006 (4)
O270.0310 (5)0.0335 (5)0.0353 (5)0.0063 (4)0.0068 (4)0.0003 (4)
Geometric parameters (Å, º) top
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C2—C31.5138 (18)C16—O171.4214 (19)
C2—O11.4160 (16)C18—H18A0.9900
C3—H3A0.9900C18—H18B0.9900
C3—H3B0.9900C18—C191.495 (2)
C3—O41.4267 (15)C18—O171.4114 (18)
C5—C61.3841 (18)C19—H19A0.9900
C5—C101.4085 (18)C19—H19B0.9900
C5—O41.3646 (15)C19—O201.4321 (16)
C6—H60.9500C21—C221.3817 (19)
C6—C71.3977 (19)C21—C261.4151 (18)
C7—H70.9500C21—O201.3585 (16)
C7—C81.377 (2)C22—H220.9500
C8—H80.9500C22—C231.392 (2)
C8—C91.391 (2)C23—H230.9500
C9—H90.9500C23—C241.374 (2)
C9—C101.3858 (19)C24—H240.9500
C10—O111.3678 (16)C24—C251.395 (2)
C12—H12A0.9900C25—H250.9500
C12—H12B0.9900C25—C261.3834 (19)
C12—C131.505 (2)C26—O271.3654 (16)
C12—O111.4308 (15)C28—H28A0.9900
C13—H13A0.9900C28—H28B0.9900
C13—H13B0.9900C28—C291.5087 (19)
C13—O141.4159 (18)C28—O271.4321 (15)
C15—H15A0.9900C29—H29A0.9900
C15—H15B0.9900C29—H29B0.9900
C15—C161.483 (2)C29—O11.4216 (16)
C15—O141.4328 (19)
H2A—C2—H2B108.7O17—C16—H16A109.7
C3—C2—H2A110.6O17—C16—H16B109.7
C3—C2—H2B110.6H18A—C18—H18B108.1
O1—C2—H2A110.6C19—C18—H18A109.6
O1—C2—H2B110.6C19—C18—H18B109.6
O1—C2—C3105.76 (10)O17—C18—H18A109.6
C2—C3—H3A110.5O17—C18—H18B109.6
C2—C3—H3B110.5O17—C18—C19110.35 (12)
H3A—C3—H3B108.7C18—C19—H19A110.4
O4—C3—C2106.26 (10)C18—C19—H19B110.4
O4—C3—H3A110.5H19A—C19—H19B108.6
O4—C3—H3B110.5O20—C19—C18106.42 (12)
C6—C5—C10119.54 (12)O20—C19—H19A110.4
O4—C5—C6125.21 (12)O20—C19—H19B110.4
O4—C5—C10115.24 (11)C22—C21—C26119.51 (12)
C5—C6—H6120.1O20—C21—C22125.29 (12)
C5—C6—C7119.89 (12)O20—C21—C26115.20 (12)
C7—C6—H6120.1C21—C22—H22119.9
C6—C7—H7119.8C21—C22—C23120.14 (13)
C8—C7—C6120.39 (13)C23—C22—H22119.9
C8—C7—H7119.8C22—C23—H23119.7
C7—C8—H8119.9C24—C23—C22120.62 (13)
C7—C8—C9120.23 (12)C24—C23—H23119.7
C9—C8—H8119.9C23—C24—H24120.1
C8—C9—H9120.0C23—C24—C25119.86 (13)
C10—C9—C8119.91 (12)C25—C24—H24120.1
C10—C9—H9120.0C24—C25—H25119.8
C9—C10—C5120.01 (12)C26—C25—C24120.31 (13)
O11—C10—C5115.27 (11)C26—C25—H25119.8
O11—C10—C9124.71 (12)C25—C26—C21119.55 (13)
H12A—C12—H12B108.4O27—C26—C21115.01 (12)
C13—C12—H12A110.1O27—C26—C25125.43 (12)
C13—C12—H12B110.1H28A—C28—H28B108.4
O11—C12—H12A110.1C29—C28—H28A110.1
O11—C12—H12B110.1C29—C28—H28B110.1
O11—C12—C13107.87 (12)O27—C28—H28A110.1
C12—C13—H13A108.4O27—C28—H28B110.1
C12—C13—H13B108.4O27—C28—C29108.05 (11)
H13A—C13—H13B107.5C28—C29—H29A109.2
O14—C13—C12115.47 (12)C28—C29—H29B109.2
O14—C13—H13A108.4H29A—C29—H29B107.9
O14—C13—H13B108.4O1—C29—C28111.89 (11)
H15A—C15—H15B108.1O1—C29—H29A109.2
C16—C15—H15A109.5O1—C29—H29B109.2
C16—C15—H15B109.5C2—O1—C29114.92 (10)
O14—C15—H15A109.5C5—O4—C3116.94 (10)
O14—C15—H15B109.5C10—O11—C12117.42 (10)
O14—C15—C16110.73 (12)C13—O14—C15113.46 (11)
C15—C16—H16A109.7C18—O17—C16111.29 (12)
C15—C16—H16B109.7C21—O20—C19117.34 (11)
H16A—C16—H16B108.2C26—O27—C28117.35 (10)
O17—C16—C15109.99 (13)
C2—C3—O4—C5178.30 (10)C22—C21—C26—O27177.94 (11)
C3—C2—O1—C29171.31 (11)C22—C21—O20—C194.54 (19)
C5—C6—C7—C81.1 (2)C22—C23—C24—C250.2 (2)
C5—C10—O11—C12160.54 (11)C23—C24—C25—C260.4 (2)
C6—C5—C10—C91.36 (19)C24—C25—C26—C211.10 (19)
C6—C5—C10—O11178.08 (11)C24—C25—C26—O27177.90 (12)
C6—C5—O4—C33.98 (18)C25—C26—O27—C285.00 (18)
C6—C7—C8—C91.1 (2)C26—C21—C22—C230.55 (19)
C7—C8—C9—C100.2 (2)C26—C21—O20—C19174.39 (11)
C8—C9—C10—C51.4 (2)C28—C29—O1—C2100.04 (14)
C8—C9—C10—O11177.99 (12)C29—C28—O27—C26178.62 (10)
C9—C10—O11—C1220.06 (18)O1—C2—C3—O4176.91 (10)
C10—C5—C6—C70.11 (19)O4—C5—C6—C7179.02 (12)
C10—C5—O4—C3175.18 (11)O4—C5—C10—C9177.86 (11)
C12—C13—O14—C1578.08 (17)O4—C5—C10—O112.71 (16)
C13—C12—O11—C10176.07 (11)O11—C12—C13—O1464.62 (16)
C15—C16—O17—C18179.56 (12)O14—C15—C16—O1772.03 (17)
C16—C15—O14—C13155.01 (14)O17—C18—C19—O2071.48 (15)
C18—C19—O20—C21174.35 (11)O20—C21—C22—C23179.43 (12)
C19—C18—O17—C16146.68 (13)O20—C21—C26—C25179.85 (11)
C21—C22—C23—C240.1 (2)O20—C21—C26—O271.05 (16)
C21—C26—O27—C28175.96 (11)O27—C28—C29—O185.10 (13)
C22—C21—C26—C251.16 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O11i0.992.943.8408 (17)152
C6—H6···O1ii0.952.693.5630 (16)154
C7—H7···O27iii0.953.364.2170 (17)152
C13—H13B···O14iv0.993.364.3366 (18)170
C16—H16A···O17i0.993.314.292 (2)172
C19—H19B···O20v0.993.114.0729 (18)165
C29—H29A···O17i0.992.953.9337 (18)172
C29—H29B···O1i0.993.524.4497 (17)156
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x, y+2, z+1; (v) x1, y, z.
 

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