#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024512.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_4024512
loop_
_publ_author_name
'Roman A. Valiulin'
'Donald G. Dressen'
'Jennifer R. Riggs'
'Faven M. Habte'
'Andrei G. Kutateladze'
_publ_section_title
;
Effect of Intramolecular Paternò-Büchi Reaction on the Thermodynamics
and Kinetics of Nearly Degenerate [3,3]-Sigmatropic Shift in Fluxional
Polycycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3484
_journal_page_last               3490
_journal_paper_doi               10.1021/jo9003822
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C32 H28 O2'
_chemical_formula_sum            'C32 H28 O2'
_chemical_formula_weight         444.54
_chemical_name_common            '2:1 cot adduct with dibenzoylethene'
_chemical_name_systematic
; 
trans-17,18-dibenzoyl-anti,anti-hexacyclo[8.3.3.2(4,7).0(2,9).0(3,8).0(13,14)]
octadeca-5,11,15-triene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.28(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.99(4)
_cell_length_b                   13.390(17)
_cell_length_c                   11.462(15)
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.0
_cell_volume                     2398(7)
_computing_cell_refinement       'Rigaku SCXmini'
_computing_data_collection       'Rigaku SCXmini'
_computing_data_reduction        'Rigaku SCXmini'
_computing_molecular_graphics    Rigaku
_computing_publication_material  Rigaku
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16014
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5409
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0628P)²+0.6234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1825
_reflns_number_gt                2885
_reflns_number_total             5409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9003822_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4024512
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
O1A O 0.11938(16) -0.48761(18) 0.2256(2) 0.0830(8) Uani 0.893(2) 1 d PD A 1
O2A O 0.24421(14) -0.71521(16) 0.03154(17) 0.0618(6) Uani 0.893(2) 1 d PD A 1
C1A C 0.15024(17) -0.39125(15) 0.0650(2) 0.0491(7) Uani 0.893(2) 1 d PGD A 1
C2A C 0.19839(13) -0.37777(17) -0.0215(3) 0.0555(8) Uani 0.893(2) 1 d PGD A 1
H2A H 0.2434 -0.4218 -0.0255 0.072 Uiso 0.893(2) 1 calc PR A 1
C3A C 0.17992(19) -0.2991(2) -0.1020(2) 0.0659(10) Uani 0.893(2) 1 d PGD A 1
H3A H 0.2125 -0.2900 -0.1605 0.086 Uiso 0.893(2) 1 calc PR A 1
C4A C 0.1133(2) -0.23395(18) -0.0961(3) 0.0745(11) Uani 0.893(2) 1 d PGD A 1
H4A H 0.1008 -0.1808 -0.1505 0.097 Uiso 0.893(2) 1 calc PR A 1
C5A C 0.06514(17) -0.2474(2) -0.0096(3) 0.0834(12) Uani 0.893(2) 1 d PGD A 1
H5A H 0.0201 -0.2034 -0.0056 0.108 Uiso 0.893(2) 1 calc PR A 1
C6A C 0.08361(17) -0.3261(2) 0.0709(2) 0.0692(10) Uani 0.893(2) 1 d PGD A 1
H6A H 0.0510 -0.3352 0.1294 0.090 Uiso 0.893(2) 1 calc PR A 1
C7A C 0.16784(19) -0.4740(2) 0.1569(3) 0.0531(8) Uani 0.893(2) 1 d PD A 1
C8A C 0.17140(12) -0.81506(12) 0.1494(2) 0.0445(7) Uani 0.893(2) 1 d PGD A 1
C9A C 0.14980(14) -0.88385(19) 0.05711(14) 0.0526(8) Uani 0.893(2) 1 d PGD A 1
H9A H 0.1653 -0.8720 -0.0163 0.068 Uiso 0.893(2) 1 calc PR A 1
C10A C 0.10527(17) -0.97011(17) 0.0733(2) 0.0635(9) Uani 0.893(2) 1 d PGD A 1
H10A H 0.0907 -1.0166 0.0109 0.083 Uiso 0.893(2) 1 calc PR A 1
C11A C 0.08234(17) -0.98758(14) 0.1819(3) 0.0720(11) Uani 0.893(2) 1 d PGD A 1
H11A H 0.0522 -1.0459 0.1929 0.094 Uiso 0.893(2) 1 calc PR A 1
C12A C 0.10394(16) -0.9188(2) 0.27426(18) 0.0700(10) Uani 0.893(2) 1 d PGD A 1
H12A H 0.0884 -0.9306 0.3477 0.091 Uiso 0.893(2) 1 calc PR A 1
C13A C 0.14847(13) -0.83254(15) 0.25801(16) 0.0534(8) Uani 0.893(2) 1 d PGD A 1
H13A H 0.1631 -0.7860 0.3205 0.069 Uiso 0.893(2) 1 calc PR A 1
C14A C 0.22033(17) -0.7233(2) 0.1262(2) 0.0439(7) Uani 0.893(2) 1 d PD A 1
O1B O 0.2523(11) -0.5602(13) -0.0104(14) 0.067(5) Uani 0.107(2) 1 d PD A 2
O2B O 0.1146(12) -0.6417(13) 0.290(2) 0.083(6) Uani 0.107(2) 1 d PD A 2
C1B C 0.1775(14) -0.4119(12) 0.017(2) 0.0491(7) Uani 0.107(2) 1 d PGD A 2
C2B C 0.1959(13) -0.358(2) -0.077(2) 0.0555(8) Uani 0.107(2) 1 d PGD A 2
H2B H 0.2383 -0.3802 -0.1167 0.072 Uiso 0.107(2) 1 calc PR A 2
C3B C 0.1515(19) -0.270(2) -0.1144(19) 0.0659(10) Uani 0.107(2) 1 d PGD A 2
H3B H 0.1640 -0.2333 -0.1786 0.086 Uiso 0.107(2) 1 calc PR A 2
C4B C 0.0888(19) -0.2365(17) -0.056(3) 0.0745(11) Uani 0.107(2) 1 d PGD A 2
H4B H 0.0588 -0.1773 -0.0814 0.097 Uiso 0.107(2) 1 calc PR A 2
C5B C 0.0704(16) -0.291(2) 0.038(3) 0.0834(12) Uani 0.107(2) 1 d PGD A 2
H5B H 0.0280 -0.2682 0.0777 0.108 Uiso 0.107(2) 1 calc PR A 2
C6B C 0.1148(16) -0.3784(19) 0.0754(19) 0.0692(10) Uani 0.107(2) 1 d PGD A 2
H6B H 0.1024 -0.4151 0.1395 0.090 Uiso 0.107(2) 1 calc PR A 2
C7B C 0.2236(14) -0.5075(14) 0.059(2) 0.0531(8) Uani 0.107(2) 1 d PD A 2
C8B C 0.1378(13) -0.7980(9) 0.2078(18) 0.0445(7) Uani 0.107(2) 1 d PGD A 2
C9B C 0.1533(14) -0.8352(14) 0.1011(17) 0.0526(8) Uani 0.107(2) 1 d PGD A 2
H9B H 0.1797 -0.7946 0.0525 0.068 Uiso 0.107(2) 1 calc PR A 2
C10B C 0.1299(17) -0.9325(16) 0.0664(17) 0.0635(9) Uani 0.107(2) 1 d PGD A 2
H10B H 0.1404 -0.9577 -0.0057 0.083 Uiso 0.107(2) 1 calc PR A 2
C11B C 0.0909(18) -0.9926(11) 0.138(3) 0.0720(11) Uani 0.107(2) 1 d PGD A 2
H11B H 0.0750 -1.0584 0.1148 0.094 Uiso 0.107(2) 1 calc PR A 2
C12B C 0.0754(16) -0.9554(15) 0.245(2) 0.0700(10) Uani 0.107(2) 1 d PGD A 2
H12B H 0.0490 -0.9960 0.2935 0.091 Uiso 0.107(2) 1 calc PR A 2
C13B C 0.0988(14) -0.8581(16) 0.2796(14) 0.0534(8) Uani 0.107(2) 1 d PGD A 2
H13B H 0.0883 -0.8330 0.3517 0.069 Uiso 0.107(2) 1 calc PR A 2
C14B C 0.1624(13) -0.6917(12) 0.2421(18) 0.0439(7) Uani 0.107(2) 1 d PD A 2
C15 C 0.24759(16) -0.53786(18) 0.1669(2) 0.0487(6) Uani 1 1 d . . .
H15A H 0.2568 -0.5473 0.0849 0.063 Uiso 0.893(2) 1 calc PR A 1
H15B H 0.2035 -0.5037 0.2014 0.063 Uiso 0.107(2) 1 calc PR A 2
C16 C 0.32895(16) -0.48248(19) 0.2401(2) 0.0492(6) Uani 1 1 d . A .
H16 H 0.3298 -0.4113 0.2170 0.064 Uiso 1 1 calc R . .
C17 C 0.33185(17) -0.4941(2) 0.3714(3) 0.0611(8) Uani 1 1 d . . .
H17 H 0.3333 -0.4392 0.4228 0.079 Uiso 1 1 calc R A .
C18 C 0.33222(16) -0.5872(2) 0.4089(2) 0.0585(8) Uani 1 1 d . A .
H18 H 0.3359 -0.6035 0.4896 0.076 Uiso 1 1 calc R . .
C19 C 0.32624(15) -0.66612(19) 0.3124(2) 0.0478(6) Uani 1 1 d . . .
H19 H 0.3258 -0.7344 0.3455 0.062 Uiso 1 1 calc R A .
C20 C 0.24051(15) -0.64248(18) 0.2192(2) 0.0445(6) Uani 1 1 d . A .
H20A H 0.1935 -0.6408 0.2631 0.058 Uiso 0.893(2) 1 calc PR A 1
H20B H 0.2499 -0.6837 0.1514 0.058 Uiso 0.107(2) 1 calc PR A 2
C21 C 0.40611(15) -0.54062(17) 0.2107(2) 0.0410(6) Uani 1 1 d . . .
H21 H 0.4086 -0.5337 0.1255 0.053 Uiso 1 1 calc R A .
C22 C 0.40121(15) -0.65179(17) 0.2466(2) 0.0410(6) Uani 1 1 d . A .
H22 H 0.3966 -0.6973 0.1775 0.053 Uiso 1 1 calc R . .
C23 C 0.49721(15) -0.53136(17) 0.2941(2) 0.0434(6) Uani 1 1 d . A .
H23 H 0.4924 -0.4931 0.3663 0.056 Uiso 1 1 calc R . .
C24 C 0.49438(15) -0.64539(17) 0.3219(2) 0.0436(6) Uani 1 1 d . . .
H24 H 0.4949 -0.6559 0.4076 0.057 Uiso 1 1 calc R A .
C25 C 0.56005(16) -0.71385(19) 0.2824(2) 0.0502(6) Uani 1 1 d . A .
H25 H 0.5468 -0.7832 0.3023 0.065 Uiso 1 1 calc R . .
C26 C 0.65065(17) -0.6919(2) 0.3468(2) 0.0540(7) Uani 1 1 d . . .
H26 H 0.6799 -0.7419 0.3970 0.070 Uiso 1 1 calc R A .
C27 C 0.69210(16) -0.6075(2) 0.3378(2) 0.0517(7) Uani 1 1 d . A .
H27 H 0.7485 -0.6034 0.3828 0.067 Uiso 1 1 calc R . .
C28 C 0.65969(17) -0.5192(2) 0.2652(2) 0.0543(7) Uani 1 1 d . . .
H28 H 0.7015 -0.4639 0.2710 0.071 Uiso 1 1 calc R A .
C29 C 0.56697(16) -0.4856(2) 0.2408(2) 0.0517(7) Uani 1 1 d . A .
H29 H 0.5614 -0.4121 0.2336 0.067 Uiso 1 1 calc R . .
C30 C 0.60002(18) -0.5312(2) 0.1387(2) 0.0630(8) Uani 1 1 d . A .
H30 H 0.6109 -0.4824 0.0789 0.082 Uiso 1 1 calc R . .
C31 C 0.57512(18) -0.6307(3) 0.0903(2) 0.0661(8) Uani 1 1 d . . .
H31 H 0.5716 -0.6388 0.0080 0.086 Uiso 1 1 calc R A .
C32 C 0.55701(17) -0.7101(2) 0.1482(3) 0.0612(8) Uani 1 1 d . A .
H32 H 0.5411 -0.7687 0.1038 0.079 Uiso 1 1 calc R . .
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
C2A C1A C6A 120.0 . . ?
C2A C1A C7A 122.8(3) . . ?
C6A C1A C7A 117.1(3) . . ?
C3A C2A C1A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
O1A C7A C1A 120.3(3) . . ?
O1A C7A C15 120.1(3) . . ?
C1A C7A C15 119.5(3) . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A C14A 117.3(2) . . ?
C13A C8A C14A 122.7(2) . . ?
C8A C9A C10A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
O2A C14A C20 120.2(3) . . ?
O2A C14A C8A 119.8(2) . . ?
C20 C14A C8A 120.1(2) . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B C7B 122(2) . . ?
C6B C1B C7B 118(2) . . ?
C3B C2B C1B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
O1B C7B C15 111.6(15) . . ?
O1B C7B C1B 120.6(18) . . ?
C15 C7B C1B 127.1(16) . . ?
C9B C8B C13B 120.0 . . ?
C9B C8B C14B 118.9(15) . . ?
C13B C8B C14B 121.1(15) . . ?
C8B C9B C10B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C12B C13B C8B 120.0 . . ?
O2B C14B C20 117.6(14) . . ?
O2B C14B C8B 118.6(17) . . ?
C20 C14B C8B 123.8(13) . . ?
C7B C15 C7A 71.0(8) . . ?
C7B C15 C20 129.4(10) . . ?
C7A C15 C20 114.3(2) . . ?
C7B C15 C16 114.1(11) . . ?
C7A C15 C16 111.1(2) . . ?
C20 C15 C16 110.0(2) . . ?
C17 C16 C21 107.9(2) . . ?
C17 C16 C15 109.3(2) . . ?
C21 C16 C15 104.6(2) . . ?
C18 C17 C16 115.0(2) . . ?
C17 C18 C19 115.1(2) . . ?
C18 C19 C22 109.3(2) . . ?
C18 C19 C20 105.3(2) . . ?
C22 C19 C20 107.1(2) . . ?
C14B C20 C14A 75.2(7) . . ?
C14B C20 C15 127.4(8) . . ?
C14A C20 C15 113.6(2) . . ?
C14B C20 C19 115.7(8) . . ?
C14A C20 C19 111.1(2) . . ?
C15 C20 C19 108.7(2) . . ?
C22 C21 C16 109.6(2) . . ?
C22 C21 C23 90.39(17) . . ?
C16 C21 C23 120.3(2) . . ?
C21 C22 C24 89.89(17) . . ?
C21 C22 C19 109.54(19) . . ?
C24 C22 C19 118.9(2) . . ?
C29 C23 C24 122.3(2) . . ?
C29 C23 C21 117.1(2) . . ?
C24 C23 C21 89.07(17) . . ?
C25 C24 C22 116.0(2) . . ?
C25 C24 C23 118.2(2) . . ?
C22 C24 C23 90.36(17) . . ?
C26 C25 C32 107.9(2) . . ?
C26 C25 C24 112.7(2) . . ?
C32 C25 C24 113.6(2) . . ?
C27 C26 C25 124.9(3) . . ?
C26 C27 C28 127.3(3) . . ?
C27 C28 C29 123.6(2) . . ?
C27 C28 C30 120.8(2) . . ?
C29 C28 C30 58.72(19) . . ?
C23 C29 C30 124.0(2) . . ?
C23 C29 C28 125.6(2) . . ?
C30 C29 C28 62.20(19) . . ?
C31 C30 C29 123.3(2) . . ?
C31 C30 C28 120.5(2) . . ?
C29 C30 C28 59.1(2) . . ?
C32 C31 C30 127.9(3) . . ?
C31 C32 C25 124.7(3) . . ?
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
O1A C7A 1.230(4) . ?
O2A C14A 1.229(3) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A C7A 1.514(4) . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A C5A 1.3900 . ?
C5A C6A 1.3900 . ?
C7A C15 1.519(5) . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C8A C14A 1.511(3) . ?
C9A C10A 1.3900 . ?
C10A C11A 1.3900 . ?
C11A C12A 1.3900 . ?
C12A C13A 1.3900 . ?
C14A C20 1.504(4) . ?
O1B C7B 1.224(16) . ?
O2B C14B 1.230(16) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B C7B 1.504(15) . ?
C2B C3B 1.3900 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B C6B 1.3900 . ?
C7B C15 1.28(2) . ?
C8B C9B 1.3900 . ?
C8B C13B 1.3900 . ?
C8B C14B 1.507(15) . ?
C9B C10B 1.3900 . ?
C10B C11B 1.3900 . ?
C11B C12B 1.3900 . ?
C12B C13B 1.3900 . ?
C14B C20 1.484(19) . ?
C15 C20 1.538(4) . ?
C15 C16 1.576(4) . ?
C16 C17 1.504(4) . ?
C16 C21 1.555(4) . ?
C17 C18 1.318(4) . ?
C18 C19 1.518(4) . ?
C19 C22 1.557(4) . ?
C19 C20 1.580(4) . ?
C21 C22 1.551(4) . ?
C21 C23 1.568(5) . ?
C22 C24 1.557(5) . ?
C23 C29 1.510(4) . ?
C23 C24 1.563(4) . ?
C24 C25 1.533(4) . ?
C25 C26 1.508(5) . ?
C25 C32 1.529(4) . ?
C26 C27 1.325(4) . ?
C27 C28 1.475(4) . ?
C28 C29 1.517(5) . ?
C28 C30 1.565(4) . ?
C29 C30 1.512(4) . ?
C30 C31 1.465(5) . ?
C31 C32 1.318(4) . ?
