#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:06:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180287 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150120.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150120
loop_
_publ_author_name
'Wooi, Goh Yit'
'White, Jonathan M.'
_publ_section_title
;
 Structural manifestations of the cheletropic reaction.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              972
_journal_page_last               974
_journal_paper_doi               10.1039/b417538g
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C39 H24 O3'
_chemical_formula_weight         540.58
_chemical_name_systematic
;
?
;
_space_group_IT_number           176
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_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            6
_cell_length_a                   15.3580(4)
_cell_length_b                   15.3580(4)
_cell_length_c                   20.1237(12)
_cell_measurement_reflns_used    1721
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.65
_cell_volume                     4110.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25909
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1692
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00032(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0497
_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)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                1982
_reflns_number_total             3233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b417538g-cryst.txt
_cod_data_source_block           jmwrg66
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P6(3)/m  '
_cod_database_code               7150120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.01715(12) 0.77650(13) 0.39177(8) 0.0232(4) Uani 1 1 d . . .
H1 H -0.0171 0.7150 0.4156 0.028 Uiso 1 1 calc R . .
C1A C 0.00882(12) 0.77598(12) 0.32201(8) 0.0187(4) Uani 1 1 d . . .
C2 C 0.07408(13) 0.86465(13) 0.42562(9) 0.0287(4) Uani 1 1 d . . .
H2 H 0.0801 0.8640 0.4726 0.034 Uiso 1 1 calc R . .
C3 C 0.12323(14) 0.95545(14) 0.39085(9) 0.0317(5) Uani 1 1 d . . .
H3 H 0.1598 1.0169 0.4145 0.038 Uiso 1 1 calc R . .
C4 C 0.11892(13) 0.95621(13) 0.32308(9) 0.0284(5) Uani 1 1 d . . .
H4 H 0.1545 1.0185 0.3002 0.034 Uiso 1 1 calc R . .
C4A C 0.06332(12) 0.86743(12) 0.28617(8) 0.0208(4) Uani 1 1 d . . .
C10 C -0.05324(11) 0.68613(11) 0.28399(8) 0.0177(4) Uani 1 1 d . . .
C11 C -0.12808(12) 0.58004(12) 0.30895(8) 0.0184(4) Uani 1 1 d . . .
C12 C -0.20116(18) 0.55354(17) 0.2500 0.0210(6) Uani 1 2 d S . .
C15 C -0.08505(12) 0.51082(12) 0.28902(7) 0.0194(4) Uani 1 1 d . . .
H15 H -0.1352 0.4411 0.3036 0.023 Uiso 1 1 calc R . .
C16 C 0.01417(13) 0.53674(12) 0.32094(9) 0.0244(4) Uani 1 1 d . . .
C17 C 0.07781(12) 0.50492(12) 0.28439(8) 0.0269(4) Uani 1 1 d . . .
C18 C 0.14241(14) 0.48153(14) 0.31922(11) 0.0380(5) Uani 1 1 d . . .
H18 H 0.1441 0.4835 0.3664 0.046 Uiso 1 1 calc R . .
C19 C 0.20342(15) 0.45565(15) 0.28469(10) 0.0487(6) Uani 1 1 d . . .
H19 H 0.2458 0.4377 0.3082 0.058 Uiso 1 1 calc R . .
C20 C -0.17933(12) 0.56565(12) 0.37510(8) 0.0226(4) Uani 1 1 d . . .
C21 C -0.23356(13) 0.61489(13) 0.38622(9) 0.0290(5) Uani 1 1 d . . .
H21 H -0.2359 0.6570 0.3525 0.035 Uiso 1 1 calc R . .
C22 C -0.28417(14) 0.60355(14) 0.44553(10) 0.0380(5) Uani 1 1 d . . .
H22 H -0.3204 0.6380 0.4524 0.046 Uiso 1 1 calc R . .
C23 C -0.28167(15) 0.54197(15) 0.49461(10) 0.0428(6) Uani 1 1 d . . .
H23 H -0.3155 0.5344 0.5356 0.051 Uiso 1 1 calc R . .
C24 C -0.22987(15) 0.49179(14) 0.48379(9) 0.0406(6) Uani 1 1 d . . .
H24 H -0.2286 0.4491 0.5175 0.049 Uiso 1 1 calc R . .
C25 C -0.17932(14) 0.50242(13) 0.42442(9) 0.0293(5) Uani 1 1 d . . .
H25 H -0.1447 0.4664 0.4176 0.035 Uiso 1 1 calc R . .
O1 O -0.28994(13) 0.52128(14) 0.2500 0.0371(5) Uani 1 2 d S . .
O2 O 0.03923(9) 0.57775(9) 0.37483(6) 0.0344(3) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1A 120.80(16) . . ?
C2 C1 H1 119.6 . . ?
C1A C1 H1 119.6 . . ?
C1 C1A C4A 119.55(15) . . ?
C1 C1A C10 123.25(15) . . ?
C4A C1A C10 117.20(14) . . ?
C1 C2 C3 119.79(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.28(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C4A 121.87(17) . . ?
C3 C4 H4 119.1 . . ?
C4A C4 H4 119.1 . . ?
C4 C4A C1A 117.55(15) . . ?
C4 C4A C4A 121.90(10) . 10_556 ?
C1A C4A C4A 120.52(9) . 10_556 ?
C10 C10 C1A 122.02(9) 10_556 . ?
C10 C10 C11 109.11(8) 10_556 . ?
C1A C10 C11 128.87(14) . . ?
C20 C11 C10 120.29(13) . . ?
C20 C11 C12 112.56(14) . . ?
C10 C11 C12 95.07(13) . . ?
C20 C11 C15 119.74(14) . . ?
C10 C11 C15 106.98(12) . . ?
C12 C11 C15 97.06(14) . . ?
O1 C12 C11 129.68(9) . . ?
O1 C12 C11 129.68(9) . 10_556 ?
C11 C12 C11 100.65(18) . 10_556 ?
C16 C15 C11 115.22(13) . . ?
C16 C15 C15 115.14(9) . 10_556 ?
C11 C15 C15 104.91(8) . 10_556 ?
C16 C15 H15 107.0 . . ?
C11 C15 H15 107.0 . . ?
C15 C15 H15 107.0 10_556 . ?
O2 C16 C17 121.41(16) . . ?
O2 C16 C15 122.12(16) . . ?
C17 C16 C15 116.40(15) . . ?
C17 C17 C18 120.03(12) 10_556 . ?
C17 C17 C16 119.63(10) 10_556 . ?
C18 C17 C16 120.21(17) . . ?
C19 C18 C17 119.59(19) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C19 120.35(12) . 10_556 ?
C18 C19 H19 119.8 . . ?
C19 C19 H19 119.8 10_556 . ?
C25 C20 C21 118.25(16) . . ?
C25 C20 C11 123.49(16) . . ?
C21 C20 C11 118.19(16) . . ?
C22 C21 C20 121.27(18) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 119.71(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 119.54(19) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 121.10(19) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C20 C25 C24 120.10(18) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(2) . ?
C1 C1A 1.409(2) . ?
C1 H1 0.9500 . ?
C1A C4A 1.421(2) . ?
C1A C10 1.443(2) . ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.406(2) . ?
C4 H4 0.9500 . ?
C4A C4A 1.456(3) 10_556 ?
C10 C10 1.368(3) 10_556 ?
C10 C11 1.535(2) . ?
C11 C20 1.505(2) . ?
C11 C12 1.541(2) . ?
C11 C15 1.559(2) . ?
C12 O1 1.195(3) . ?
C12 C11 1.541(2) 10_556 ?
C15 C16 1.512(2) . ?
C15 C15 1.571(3) 10_556 ?
C15 H15 1.0000 . ?
C16 O2 1.2158(19) . ?
C16 C17 1.488(2) . ?
C17 C17 1.384(3) 10_556 ?
C17 C18 1.400(2) . ?
C18 C19 1.375(3) . ?
C18 H18 0.9500 . ?
C19 C19 1.396(4) 10_556 ?
C19 H19 0.9500 . ?
C20 C25 1.389(2) . ?
C20 C21 1.395(2) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C1A C4A 2.5(3) . . . . ?
C2 C1 C1A C10 -177.38(15) . . . . ?
C1A C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -3.3(3) . . . . ?
C2 C3 C4 C4A 1.9(3) . . . . ?
C3 C4 C4A C1A 1.7(3) . . . . ?
C3 C4 C4A C4A -176.41(13) . . . 10_556 ?
C1 C1A C4A C4 -3.8(2) . . . . ?
C10 C1A C4A C4 176.07(15) . . . . ?
C1 C1A C4A C4A 174.27(11) . . . 10_556 ?
C10 C1A C4A C4A -5.82(17) . . . 10_556 ?
C1 C1A C10 C10 -174.18(12) . . . 10_556 ?
C4A C1A C10 C10 5.91(17) . . . 10_556 ?
C1 C1A C10 C11 6.9(3) . . . . ?
C4A C1A C10 C11 -172.97(15) . . . . ?
C10 C10 C11 C20 -151.81(12) 10_556 . . . ?
C1A C10 C11 C20 27.2(2) . . . . ?
C10 C10 C11 C12 -31.96(12) 10_556 . . . ?
C1A C10 C11 C12 147.04(17) . . . . ?
C10 C10 C11 C15 67.02(11) 10_556 . . . ?
C1A C10 C11 C15 -113.98(17) . . . . ?
C20 C11 C12 O1 -2.7(3) . . . . ?
C10 C11 C12 O1 -128.5(3) . . . . ?
C15 C11 C12 O1 123.7(3) . . . . ?
C20 C11 C12 C11 177.38(10) . . . 10_556 ?
C10 C11 C12 C11 51.57(17) . . . 10_556 ?
C15 C11 C12 C11 -56.27(17) . . . 10_556 ?
C20 C11 C15 C16 -77.93(19) . . . . ?
C10 C11 C15 C16 63.49(17) . . . . ?
C12 C11 C15 C16 161.01(14) . . . . ?
C20 C11 C15 C15 154.39(12) . . . 10_556 ?
C10 C11 C15 C15 -64.19(11) . . . 10_556 ?
C12 C11 C15 C15 33.33(11) . . . 10_556 ?
C11 C15 C16 O2 28.0(2) . . . . ?
C15 C15 C16 O2 150.31(13) 10_556 . . . ?
C11 C15 C16 C17 -154.93(14) . . . . ?
C15 C15 C16 C17 -32.58(16) 10_556 . . . ?
O2 C16 C17 C17 -148.75(13) . . . 10_556 ?
C15 C16 C17 C17 34.11(16) . . . 10_556 ?
O2 C16 C17 C18 27.0(3) . . . . ?
C15 C16 C17 C18 -150.14(16) . . . . ?
C17 C17 C18 C19 -2.0(2) 10_556 . . . ?
C16 C17 C18 C19 -177.71(17) . . . . ?
C17 C18 C19 C19 2.0(2) . . . 10_556 ?
C10 C11 C20 C25 -127.28(17) . . . . ?
C12 C11 C20 C25 122.03(19) . . . . ?
C15 C11 C20 C25 9.0(2) . . . . ?
C10 C11 C20 C21 55.8(2) . . . . ?
C12 C11 C20 C21 -54.9(2) . . . . ?
C15 C11 C20 C21 -167.90(15) . . . . ?
C25 C20 C21 C22 1.7(3) . . . . ?
C11 C20 C21 C22 178.80(16) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C21 C20 C25 C24 -1.9(3) . . . . ?
C11 C20 C25 C24 -178.87(16) . . . . ?
C23 C24 C25 C20 0.9(3) . . . . ?
