#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513261.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1513261
loop_
_publ_author_name
'Olive, Alexandre G. L.'
'Raffy, Guillaume'
'Allouchi, Hassan'
'Léger, Jean-Michel'
'Del Guerzo, André'
'Desvergne, Jean-Pierre'
_publ_section_title
;
 Striking Correlation between the Unusual Trigonal Crystal Packing and the
 Ability to Self-Assemble into Nanofibers of
 2,3-Di-n-alkyloxyanthracenes†
;
_journal_issue                   15
_journal_name_full               Langmuir
_journal_page_first              8606
_journal_page_last               8614
_journal_paper_doi               10.1021/la804206n
_journal_volume                  25
_journal_year                    2009
_chemical_formula_sum            'C22 H26 O2'
_chemical_formula_weight         322.5
_chemical_name_common            2,3-dibutoxy-anthracene
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   14.6672(4)
_cell_length_b                   14.6672(4)
_cell_length_c                   46.706(2)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      4.3
_cell_volume                     8701.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            3242
_diffrn_reflns_theta_full        22.0
_diffrn_reflns_theta_max         22.0
_diffrn_reflns_theta_min         4.3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   scalepack
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_description       platelet
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.068
_refine_diff_density_min         -0.052
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         1938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.121
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          -0.052
_refine_ls_shift/su_mean         0.068
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.6276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.166
_reflns_number_gt                1023
_reflns_number_total             2048
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            la804206nsup2.cif
_cod_data_source_block           A4-DBOA
_cod_original_cell_volume        8701.5(8)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               1513261
loop_
_symmetry_equiv_pos_as_xyz
'  x,      y,      z'
'  x+1/3,  y+2/3,  z+2/3'
'  x+2/3,  y+1/3,  z+1/3'
' -y,      x-y,    z'
'  1/3-y, 2/3+x-y, 2/3+z'
'  2/3-y, 1/3+x-y, 1/3+z'
' -x+y,   -x,      z'
'  1/3+y-x, 2/3-x, 2/3+z'
'  2/3+y-x, 1/3-x, 1/3+z'
' -x,     -y,     -z'
' -x+1/3,  -y+2/3,  -z+2/3'
' -x+2/3,  -y+1/3,  -z+1/3'
'  y,     -x+y,   -z'
'  1/3+y, 2/3+y-x, 2/3-z'
'  2/3+y, 1/3+y-x, 1/3-z'
'  x-y,    x,     -z'
'  1/3+x-y, 2/3+x, 2/3-z'
'  2/3+x-y, 1/3+x, 1/3-z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.1637(3) 0.9947(3) 0.1636(1) 4.6(2) Bani 1 1 d
C2 C 0.1680(3) 0.9518(3) 0.1887(1) 4.5(2) Bani 1 1 d
C3 C 0.1445(3) 0.8438(3) 0.1898(1) 4.4(2) Bani 1 1 d
C4 C 0.1136(3) 0.7845(3) 0.1659(1) 4.8(2) Bani 1 1 d
C5 C 0.1100(3) 0.8272(3) 0.1389(1) 4.2(2) Bani 1 1 d
C6 C 0.0850(3) 0.7703(3) 0.1138(1) 4.8(2) Bani 1 1 d
C7 C 0.0897(3) 0.8143(4) 0.0872(1) 4.9(3) Bani 1 1 d
C8 C 0.0682(4) 0.7577(4) 0.0611(2) 5.8(3) Bani 1 1 d
C9 C 0.0791(4) 0.8049(6) 0.0357(2) 6.6(3) Bani 1 1 d
C10 C 0.1105(4) 0.9126(6) 0.0344(2) 6.3(3) Bani 1 1 d
C11 C 0.1286(4) 0.9697(4) 0.0584(2) 5.6(3) Bani 1 1 d
C12 C 0.1199(3) 0.9236(4) 0.0857(1) 4.8(3) Bani 1 1 d
C13 C 0.1408(3) 0.9802(4) 0.1110(1) 4.8(3) Bani 1 1 d
C14 C 0.1381(3) 0.9360(3) 0.1378(1) 4.3(2) Bani 1 1 d
O20 O 0.1949(2) 1.0009(2) 0.21469(7) 5.2(2) Bani 1 1 d
C21 C 0.2260(5) 1.1110(4) 0.2158(1) 6.3(3) Bani 1 1 d
C22 C 0.2642(5) 1.1475(4) 0.2461(2) 6.5(3) Bani 1 1 d
C23 C 0.1836(7) 1.0959(6) 0.2686(2) 9.1(4) Bani 1 1 d
C24 C 0.2238(9) 1.1352(7) 0.2984(2) 10.2(5) Bani 1 1 d
O30 O 0.1573(2) 0.8134(2) 0.21644(7) 5.1(2) Bani 1 1 d
C31 C 0.1418(4) 0.7090(3) 0.2194(1) 5.9(3) Bani 1 1 d
C32 C 0.1863(5) 0.7053(4) 0.2484(2) 7.2(3) Bani 1 1 d
C33 C 0.1331(5) 0.7203(5) 0.2731(2) 7.7(3) Bani 1 1 d
C34 C 0.1832(8) 0.7198(7) 0.3020(2) 10.3(5) Bani 1 1 d
H51 H 0.183(1) 1.065(1) 0.1631(5) 5.1(5) Biso 1 1 d
H41 H 0.099(1) 0.714(2) 0.1673(5) 6.0(6) Biso 1 1 d
H61 H 0.069(1) 0.703(1) 0.1160(5) 5.0(5) Biso 1 1 d
H81 H 0.051(2) 0.690(2) 0.0622(6) 6.5(6) Biso 1 1 d
H91 H 0.057(2) 0.765(2) 0.0183(6) 7.6(7) Biso 1 1 d
H101 H 0.113(2) 0.942(2) 0.0163(7) 8.1(7) Biso 1 1 d
H111 H 0.153(2) 1.048(2) 0.0587(6) 7.7(7) Biso 1 1 d
H131 H 0.156(1) 1.053(2) 0.1100(6) 6.7(6) Biso 1 1 d
H211 H 0.166(2) 1.109(2) 0.2095(6) 6.4(6) Biso 1 1 d
H212 H 0.278(3) 1.149(3) 0.1999(9) 13(1) Biso 1 1 d
H221 H 0.299(2) 1.225(2) 0.2470(8) 10.2(9) Biso 1 1 d
H222 H 0.324(3) 1.130(3) 0.253(1) 14(1) Biso 1 1 d
H231 H 0.157(3) 1.021(3) 0.268(1) 16(1) Biso 1 1 d
H232 H 0.125(2) 1.107(2) 0.2646(7) 7.6(7) Biso 1 1 d
H241 H 0.168(4) 1.099(5) 0.312(2) 21(2) Biso 1 1 d
H242 H 0.249(3) 1.209(4) 0.299(1) 18(2) Biso 1 1 d
H243 H 0.280(7) 1.123(7) 0.303(2) 27(3) Biso 1 1 d
H311 H 0.183(2) 0.701(2) 0.2036(7) 8.3(7) Biso 1 1 d
H312 H 0.067(2) 0.662(2) 0.2185(6) 7.3(7) Biso 1 1 d
H321 H 0.263(2) 0.767(2) 0.2553(8) 11(1) Biso 1 1 d
H322 H 0.177(2) 0.635(2) 0.2508(8) 10.2(9) Biso 1 1 d
H331 H 0.054(3) 0.663(3) 0.267(1) 14(1) Biso 1 1 d
H332 H 0.140(2) 0.791(2) 0.2714(6) 8.7(8) Biso 1 1 d
H341 H 0.140(6) 0.729(6) 0.320(2) 24(3) Biso 1 1 d
H342 H 0.255(4) 0.770(4) 0.303(2) 19(2) Biso 1 1 d
H343 H 0.184(4) 0.641(4) 0.303(1) 18(2) Biso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C14 121.1(5)
C1 C2 C3 120.2(5)
C1 C2 O20 126.6(5)
C3 C2 O20 113.2(4)
C2 C3 C4 119.8(5)
C2 C3 O30 113.2(4)
C4 C3 O30 126.9(5)
C3 C4 C5 121.7(5)
C4 C5 C6 123.1(5)
C4 C5 C14 117.9(5)
C6 C5 C14 119.0(5)
C5 C6 C7 123.0(6)
C6 C7 C8 123.6(6)
C6 C7 C12 118.7(5)
C8 C7 C12 117.8(6)
C7 C8 C9 121.6(7)
C8 C9 C10 120.3(8)
C9 C10 C11 121.0(8)
C10 C11 C12 120.7(7)
C7 C12 C11 118.7(6)
C7 C12 C13 118.6(6)
C11 C12 C13 122.7(6)
C12 C13 C14 122.5(6)
C1 C14 C5 119.1(5)
C1 C14 C13 122.7(5)
C5 C14 C13 118.2(5)
C2 O20 C21 117.9(4)
O20 C21 C22 106.4(5)
C21 C22 C23 115.0(7)
C22 C23 C24 113.6(9)
C3 O30 C31 117.4(4)
O30 C31 C32 106.4(5)
C31 C32 C33 115.2(7)
C32 C33 C34 113.4(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.347(8)
C1 C14 1.418(8)
C2 C3 1.444(7)
C2 O20 1.365(6)
C3 C4 1.347(8)
C3 O30 1.366(6)
C4 C5 1.421(8)
C5 C6 1.378(8)
C5 C14 1.436(8)
C6 C7 1.386(8)
C7 C8 1.42(1)
C7 C12 1.436(9)
C8 C9 1.34(1)
C9 C10 1.41(1)
C10 C11 1.34(1)
C11 C12 1.419(9)
C12 C13 1.387(9)
C13 C14 1.401(8)
O20 C21 1.443(8)
C21 C22 1.52(1)
C22 C23 1.48(1)
C23 C24 1.51(2)
O30 C31 1.438(7)
C31 C32 1.52(1)
C32 C33 1.47(1)
C33 C34 1.54(1)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C14 C1 C2 C3 -1.1(5)
C14 C1 C2 O20 177.7(5)
C2 C1 C14 C5 3.9(5)
C2 C1 C14 C13 -174.9(6)
C1 C2 C3 C4 -3.0(5)
C1 C2 C3 O30 176.9(5)
O20 C2 C3 C4 178.0(5)
O20 C2 C3 O30 -2.1(4)
C1 C2 O20 C21 -2.5(5)
C3 C2 O20 C21 176.4(5)
C2 C3 C4 C5 4.3(5)
O30 C3 C4 C5 -175.7(5)
C2 C3 O30 C31 -176.4(5)
C4 C3 O30 C31 3.5(5)
C3 C4 C5 C6 175.9(6)
C3 C4 C5 C14 -1.5(5)
C4 C5 C6 C7 -174.7(6)
C14 C5 C6 C7 2.7(5)
C4 C5 C14 C1 -2.6(5)
C4 C5 C14 C13 176.2(5)
C6 C5 C14 C1 179.9(5)
C6 C5 C14 C13 -1.2(5)
C5 C6 C7 C8 177.4(6)
C5 C6 C7 C12 -1.3(6)
C6 C7 C8 C9 -176.4(7)
C12 C7 C8 C9 2.3(7)
C6 C7 C12 C11 177.6(6)
C6 C7 C12 C13 -1.5(6)
C8 C7 C12 C11 -1.2(6)
C8 C7 C12 C13 179.7(6)
C9 C10 C11 C12 2.1(7)
C7 C12 C13 C14 2.9(6)
C11 C12 C13 C14 -176.2(6)
C12 C13 C14 C1 177.3(6)
C12 C13 C14 C5 -1.6(6)
C2 O20 C21 C22 -173.0(5)
O20 C21 C22 C23 -63.2(7)
C3 O30 C31 C32 166.3(5)
O30 C31 C32 C33 63.2(6)
C31 C32 C33 C34 -178.0(7)
