#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/58/2205877.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2205877
loop_
_publ_author_name
'V. Vinodhkumar'
'S. Selvanayagam'
'D. Velmurugan'
'K. Ravikumar'
'M. Poornachandran'
'R. Raghunathan'
_publ_section_title
;
 8,12-Dioxa-1,7,10(1,2)-tribenzenacyclododecaphane-2,5-dien-4-one
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1839
_journal_page_last               o1841
_journal_paper_doi               10.1107/S1600536805015631
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C25 H20 O3'
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.41
_chemical_name_systematic
;
8,12-Dioxa-1,7,10(1,2)-tribenzenacyclododecaphane-2,5-dien-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                108.074(2)
_cell_angle_beta                 94.933(2)
_cell_angle_gamma                109.974(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7602(11)
_cell_length_b                   9.8884(14)
_cell_length_c                   13.965(2)
_cell_measurement_reflns_used    4247
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.30
_cell_volume                     935.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'Bruker SMART APEX area-detector'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ω
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7971
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0895P)²+0.1401P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1523
_reflns_number_gt                3395
_reflns_number_total             4160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6669.cif
_cod_data_source_block           I
_cod_database_code               2205877
_cod_database_fobs_code          2205877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 1.0511(2) 0.80789(16) 0.11085(12) 0.0469(4) Uani d . 1 C
C2 0.8890(2) 0.66464(16) 0.05059(11) 0.0445(3) Uani d . 1 C
H2 0.8250 0.6611 -0.0102 0.053 Uiso calc R 1 H
C3 0.82606(19) 0.54002(15) 0.07530(10) 0.0395(3) Uani d . 1 C
H3 0.8865 0.5453 0.1376 0.047 Uiso calc R 1 H
C4 0.67015(18) 0.39509(15) 0.01318(10) 0.0375(3) Uani d . 1 C
C5 0.6098(2) 0.35398(18) -0.09239(12) 0.0479(3) Uani d . 1 C
H5 0.6693 0.4210 -0.1245 0.058 Uiso calc R 1 H
C6 0.4635(2) 0.2158(2) -0.15052(13) 0.0557(4) Uani d . 1 C
H6 0.4241 0.1904 -0.2209 0.067 Uiso calc R 1 H
C7 0.3765(2) 0.11569(18) -0.10278(13) 0.0564(4) Uani d . 1 C
H7 0.2789 0.0220 -0.1417 0.068 Uiso calc R 1 H
C8 0.4318(2) 0.15238(16) 0.00102(13) 0.0485(4) Uani d . 1 C
H8 0.3717 0.0839 0.0320 0.058 Uiso calc R 1 H
C9 0.57791(18) 0.29219(15) 0.06006(10) 0.0375(3) Uani d . 1 C
C10 0.5311(2) 0.2708(2) 0.22616(13) 0.0495(4) Uani d . 1 C
H10A 0.6111 0.2848 0.2887 0.059 Uiso calc R 1 H
H10B 0.4648 0.1608 0.1886 0.059 Uiso calc R 1 H
C11 0.39128(18) 0.34252(16) 0.25412(11) 0.0409(3) Uani d . 1 C
C12 0.2092(2) 0.26945(16) 0.19495(11) 0.0441(3) Uani d . 1 C
H12 0.1754 0.1749 0.1416 0.053 Uiso calc R 1 H
C13 0.0774(2) 0.33345(19) 0.21323(12) 0.0496(4) Uani d . 1 C
H13 -0.0432 0.2827 0.1722 0.059 Uiso calc R 1 H
C14 0.1244(2) 0.4721(2) 0.29209(13) 0.0553(4) Uani d . 1 C
H14 0.0367 0.5167 0.3041 0.066 Uiso calc R 1 H
C15 0.3029(3) 0.54508(19) 0.35354(13) 0.0563(4) Uani d . 1 C
H15 0.3337 0.6386 0.4074 0.068 Uiso calc R 1 H
C16 0.4378(2) 0.48239(17) 0.33694(11) 0.0471(4) Uani d . 1 C
C17 0.6229(2) 0.5644(2) 0.41347(13) 0.0628(5) Uani d . 1 C
H17A 0.6085 0.6305 0.4773 0.075 Uiso calc R 1 H
H17B 0.6638 0.4892 0.4284 0.075 Uiso calc R 1 H
C18 0.9284(2) 0.75364(17) 0.43797(11) 0.0480(3) Uani d . 1 C
C19 0.9782(3) 0.7678(2) 0.53958(13) 0.0609(4) Uani d . 1 C
H19 0.8947 0.7066 0.5678 0.073 Uiso calc R 1 H
C20 1.1521(3) 0.8733(2) 0.59843(14) 0.0668(5) Uani d . 1 C
H20 1.1859 0.8830 0.6665 0.080 Uiso calc R 1 H
C21 1.2761(2) 0.9642(2) 0.55716(14) 0.0686(5) Uani d . 1 C
H21 1.3924 1.0363 0.5975 0.082 Uiso calc R 1 H
C22 1.2275(2) 0.9480(2) 0.45637(13) 0.0588(4) Uani d . 1 C
H22 1.3126 1.0096 0.4291 0.071 Uiso calc R 1 H
C23 1.05437(19) 0.84185(16) 0.39363(11) 0.0448(3) Uani d . 1 C
C24 1.00191(19) 0.81277(16) 0.28428(11) 0.0444(3) Uani d . 1 C
H24 0.8742 0.7638 0.2547 0.053 Uiso calc R 1 H
C25 1.1147(2) 0.84782(17) 0.22193(13) 0.0500(4) Uani d . 1 C
H25 1.2425 0.9012 0.2503 0.060 Uiso calc R 1 H
O1 1.13345(19) 0.89330(13) 0.06763(10) 0.0691(4) Uani d . 1 O
O2 0.64629(13) 0.33824(12) 0.16376(8) 0.0469(3) Uani d . 1 O
O3 0.75888(15) 0.65394(14) 0.37311(8) 0.0620(3) Uani d . 1 O
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
_geom_angle_publ_flag
O1 C1 C2 119.44(14) ?
O1 C1 C25 120.29(13) ?
C2 C1 C25 120.27(12) ?
C3 C2 C1 125.68(14) ?
C3 C2 H2 117.2 ?
C1 C2 H2 117.2 ?
C2 C3 C4 125.72(13) ?
C2 C3 H3 117.1 ?
C4 C3 H3 117.1 ?
C5 C4 C9 118.27(12) ?
C5 C4 C3 122.00(12) ?
C9 C4 C3 119.73(12) ?
C6 C5 C4 121.46(14) ?
C6 C5 H5 119.3 ?
C4 C5 H5 119.3 ?
C5 C6 C7 119.15(15) ?
C5 C6 H6 120.4 ?
C7 C6 H6 120.4 ?
C8 C7 C6 121.02(13) ?
C8 C7 H7 119.5 ?
C6 C7 H7 119.5 ?
C7 C8 C9 120.01(14) ?
C7 C8 H8 120.0 ?
C9 C8 H8 120.0 ?
O2 C9 C8 124.50(10) y
O2 C9 C4 115.40(10) y
C8 C9 C4 120.08(13) ?
O2 C10 C11 111.79(11) ?
O2 C10 H10A 109.3 ?
C11 C10 H10A 109.3 ?
O2 C10 H10B 109.3 ?
C11 C10 H10B 109.3 ?
H10A C10 H10B 107.9 ?
C12 C11 C16 118.38(13) ?
C12 C11 C10 118.98(13) ?
C16 C11 C10 122.63(13) ?
C13 C12 C11 121.75(14) ?
C13 C12 H12 119.1 ?
C11 C12 H12 119.1 ?
C14 C13 C12 119.84(15) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 119.52(15) ?
C13 C14 H14 120.2 ?
C15 C14 H14 120.2 ?
C14 C15 C16 121.67(15) ?
C14 C15 H15 119.2 ?
C16 C15 H15 119.2 ?
C15 C16 C11 118.79(14) ?
C15 C16 C17 117.46(15) ?
C11 C16 C17 123.64(15) ?
O3 C17 C16 109.96(12) ?
O3 C17 H17A 109.7 ?
C16 C17 H17A 109.7 ?
O3 C17 H17B 109.7 ?
C16 C17 H17B 109.7 ?
H17A C17 H17B 108.2 ?
O3 C18 C19 124.40(10) y
O3 C18 C23 114.70(10) y
C19 C18 C23 120.88(14) ?
C20 C19 C18 119.57(17) ?
C20 C19 H19 120.2 ?
C18 C19 H19 120.2 ?
C21 C20 C19 120.46(16) ?
C21 C20 H20 119.8 ?
C19 C20 H20 119.8 ?
C22 C21 C20 119.75(15) ?
C22 C21 H21 120.1 ?
C20 C21 H21 120.1 ?
C21 C22 C23 121.84(17) ?
C21 C22 H22 119.1 ?
C23 C22 H22 119.1 ?
C22 C23 C18 117.46(14) ?
C22 C23 C24 123.74(14) ?
C18 C23 C24 118.72(12) ?
C25 C24 C23 127.65(14) ?
C25 C24 H24 116.2 ?
C23 C24 H24 116.2 ?
C24 C25 C1 124.32(14) ?
C24 C25 H25 117.8 ?
C1 C25 H25 117.8 ?
C9 O2 C10 120.03(11) ?
C18 O3 C17 117.83(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.225(2) y
C1 C2 1.469(2) ?
C1 C25 1.470(2) ?
C2 C3 1.326(2) y
C2 H2 0.9300 ?
C3 C4 1.4607(18) ?
C3 H3 0.9300 ?
C4 C5 1.392(2) ?
C4 C9 1.4045(18) ?
C5 C6 1.382(2) ?
C5 H5 0.9300 ?
C6 C7 1.382(2) ?
C6 H6 0.9300 ?
C7 C8 1.370(2) ?
C7 H7 0.9300 ?
C8 C9 1.3920(18) ?
C8 H8 0.9300 ?
C9 O2 1.371(2) y
C10 O2 1.446(2) y
C10 C11 1.503(2) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.3903(19) ?
C11 C16 1.405(2) ?
C12 C13 1.378(2) ?
C12 H12 0.9300 ?
C13 C14 1.370(2) ?
C13 H13 0.9300 ?
C14 C15 1.380(2) ?
C14 H14 0.9300 ?
C15 C16 1.389(2) ?
C15 H15 0.9300 ?
C16 C17 1.505(2) ?
C17 O3 1.410(2) y
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 O3 1.371(2) y
C18 C19 1.388(2) ?
C18 C23 1.399(2) ?
C19 C20 1.379(2) ?
C19 H19 0.9300 ?
C20 C21 1.375(3) ?
C20 H20 0.9300 ?
C21 C22 1.370(3) ?
C21 H21 0.9300 ?
C22 C23 1.392(2) ?
C22 H22 0.9300 ?
C23 C24 1.456(2) ?
C24 C25 1.325(2) y
C24 H24 0.9300 ?
C25 H25 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 O1 1_445 0.93 2.36 3.254(2) 161
C12 H12 O1 1_445 0.93 2.54 3.401(2) 154
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
_geom_torsion_publ_flag
O1 C1 C2 C3 156.24(16) ?
C25 C1 C2 C3 -23.3(2) ?
C1 C2 C3 C4 -177.08(13) ?
C2 C3 C4 C5 21.4(2) ?
C2 C3 C4 C9 -159.19(14) ?
C9 C4 C5 C6 -0.2(2) ?
C3 C4 C5 C6 179.27(14) ?
C4 C5 C6 C7 -0.6(2) ?
C5 C6 C7 C8 0.7(2) ?
C6 C7 C8 C9 -0.1(2) ?
C7 C8 C9 O2 -178.56(13) ?
C7 C8 C9 C4 -0.7(2) ?
C5 C4 C9 O2 178.86(12) ?
C3 C4 C9 O2 -0.58(18) ?
C5 C4 C9 C8 0.8(2) ?
C3 C4 C9 C8 -178.64(12) ?
O2 C10 C11 C12 96.59(15) ?
O2 C10 C11 C16 -82.31(16) ?
C16 C11 C12 C13 2.4(2) ?
C10 C11 C12 C13 -176.50(13) ?
C11 C12 C13 C14 -0.6(2) ?
C12 C13 C14 C15 -1.1(2) ?
C13 C14 C15 C16 0.7(2) ?
C14 C15 C16 C11 1.2(2) ?
C14 C15 C16 C17 -175.12(14) ?
C12 C11 C16 C15 -2.71(19) ?
C10 C11 C16 C15 176.20(12) ?
C12 C11 C16 C17 173.35(12) ?
C10 C11 C16 C17 -7.7(2) ?
C15 C16 C17 O3 -100.98(17) ?
C11 C16 C17 O3 82.91(19) ?
O3 C18 C19 C20 -179.31(17) ?
C23 C18 C19 C20 1.8(3) ?
C18 C19 C20 C21 0.0(3) ?
C19 C20 C21 C22 -1.1(3) ?
C20 C21 C22 C23 0.3(3) ?
C21 C22 C23 C18 1.4(2) ?
C21 C22 C23 C24 -175.40(16) ?
O3 C18 C23 C22 178.52(14) ?
C19 C18 C23 C22 -2.5(2) ?
O3 C18 C23 C24 -4.5(2) ?
C19 C18 C23 C24 174.52(15) ?
C22 C23 C24 C25 18.1(2) ?
C18 C23 C24 C25 -158.66(16) ?
C23 C24 C25 C1 177.00(14) ?
O1 C1 C25 C24 147.35(17) ?
C2 C1 C25 C24 -33.1(2) ?
C8 C9 O2 C10 -21.87(19) ?
C4 C9 O2 C10 160.17(12) ?
C11 C10 O2 C9 -80.0(2) y
C19 C18 O3 C17 2.7(3) ?
C23 C18 O3 C17 -178.27(16) ?
C16 C17 O3 C18 170.80(10) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654812
