#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:03:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178766 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/20/4102037.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_4102037
loop_
_publ_author_name
'Steven E. Wheeler'
'Anne J. McNeil'
'Peter Müller'
'Timothy M. Swager'
'K. N. Houk'
_publ_section_title
;
 Probing Substituent Effects in Aryl-Aryl Interactions Using
 Stereoselective Diels-Alder Cycloadditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3304
_journal_page_last               3311
_journal_paper_doi               10.1021/ja903653j
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C34 H24 O3'
_chemical_formula_weight         480.53
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 118.3760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1757(3)
_cell_length_b                   25.7175(8)
_cell_length_c                   10.2216(3)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.40
_cell_volume                     2353.53(12)
_computing_cell_refinement       'SAINT 7 (Bruker-AXS, 2005)'
_computing_data_collection       'SMART 5 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT 7 (Bruker-AXS, 2005)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52070
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0394
_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)+(0.0623P)²+0.8445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                5834
_reflns_number_total             6605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903653j_si_004.cif
_cod_data_source_block           07059
_cod_database_code               4102037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.53507(8) 0.09575(3) 0.22179(8) 0.01539(15) Uani 1 1 d . . .
O2 O 0.43554(9) 0.16716(3) 0.08453(8) 0.01962(16) Uani 1 1 d . . .
O3 O 0.59745(8) 0.03013(3) 0.38525(8) 0.01777(15) Uani 1 1 d . . .
C1 C 0.35082(10) 0.14052(4) 0.26312(10) 0.01197(17) Uani 1 1 d . . .
C2 C 0.18127(10) 0.13345(4) 0.14995(11) 0.01437(18) Uani 1 1 d . . .
H2 H 0.1402 0.1636 0.0802 0.017 Uiso 1 1 calc R . .
C3 C 0.17315(10) 0.08296(4) 0.06891(11) 0.01448(18) Uani 1 1 d . . .
C4 C 0.12691(11) 0.07756(4) -0.08178(11) 0.0184(2) Uani 1 1 d . . .
H4 H 0.0941 0.1070 -0.1455 0.022 Uiso 1 1 calc R . .
C5 C 0.12904(12) 0.02846(4) -0.13896(12) 0.0212(2) Uani 1 1 d . . .
H5 H 0.0974 0.0245 -0.2421 0.025 Uiso 1 1 calc R . .
C6 C 0.17718(12) -0.01466(4) -0.04595(12) 0.0201(2) Uani 1 1 d . . .
H6 H 0.1771 -0.0480 -0.0859 0.024 Uiso 1 1 calc R . .
C7 C 0.22576(11) -0.00909(4) 0.10620(11) 0.01657(19) Uani 1 1 d . . .
H7 H 0.2599 -0.0385 0.1700 0.020 Uiso 1 1 calc R . .
C8 C 0.22380(10) 0.03973(4) 0.16351(10) 0.01349(17) Uani 1 1 d . . .
C9 C 0.27738(10) 0.05308(4) 0.32647(10) 0.01285(17) Uani 1 1 d . . .
H9 H 0.3098 0.0216 0.3916 0.015 Uiso 1 1 calc R . .
C10 C 0.40817(10) 0.09283(3) 0.36809(10) 0.01127(16) Uani 1 1 d . . .
C11 C 0.49306(10) 0.11193(4) 0.53356(10) 0.01175(17) Uani 1 1 d . . .
H11 H 0.5333 0.0823 0.6051 0.014 Uiso 1 1 calc R . .
C12 C 0.61708(10) 0.14704(4) 0.54106(10) 0.01258(17) Uani 1 1 d . . .
C13 C 0.76970(11) 0.13889(4) 0.62554(11) 0.01540(18) Uani 1 1 d . . .
H13 H 0.8066 0.1096 0.6897 0.018 Uiso 1 1 calc R . .
C14 C 0.86845(11) 0.17440(4) 0.61479(12) 0.01781(19) Uani 1 1 d . . .
H14 H 0.9731 0.1691 0.6719 0.021 Uiso 1 1 calc R . .
C15 C 0.81519(11) 0.21737(4) 0.52150(12) 0.01784(19) Uani 1 1 d . . .
H15 H 0.8834 0.2412 0.5152 0.021 Uiso 1 1 calc R . .
C16 C 0.66146(11) 0.22562(4) 0.43689(11) 0.01582(18) Uani 1 1 d . . .
H16 H 0.6247 0.2550 0.3733 0.019 Uiso 1 1 calc R . .
C17 C 0.56298(10) 0.19046(4) 0.44659(10) 0.01293(17) Uani 1 1 d . . .
C18 C 0.39367(10) 0.19186(4) 0.35700(10) 0.01239(17) Uani 1 1 d . . .
H18 H 0.3574 0.2235 0.2927 0.015 Uiso 1 1 calc R . .
C19 C 0.43949(11) 0.13829(4) 0.17775(11) 0.01392(17) Uani 1 1 d . . .
C20 C 0.52270(10) 0.06791(4) 0.33152(10) 0.01313(17) Uani 1 1 d . . .
C21 C 0.09539(11) 0.12361(4) 0.23486(11) 0.01586(18) Uani 1 1 d . . .
C22 C -0.02985(11) 0.15075(4) 0.21774(13) 0.0215(2) Uani 1 1 d . . .
H22 H -0.0650 0.1800 0.1536 0.026 Uiso 1 1 calc R . .
C23 C -0.10323(12) 0.13429(5) 0.29629(14) 0.0263(2) Uani 1 1 d . . .
H23 H -0.1900 0.1522 0.2841 0.032 Uiso 1 1 calc R . .
C24 C -0.05048(13) 0.09201(5) 0.39208(14) 0.0250(2) Uani 1 1 d . . .
H24 H -0.1011 0.0813 0.4452 0.030 Uiso 1 1 calc R . .
C25 C 0.07662(12) 0.06511(4) 0.41079(12) 0.0193(2) Uani 1 1 d . . .
H25 H 0.1137 0.0365 0.4775 0.023 Uiso 1 1 calc R . .
C26 C 0.14796(11) 0.08072(4) 0.33046(11) 0.01509(18) Uani 1 1 d . . .
C27 C 0.39237(10) 0.14702(4) 0.56682(10) 0.01215(17) Uani 1 1 d . . .
C28 C 0.36459(10) 0.14105(4) 0.68730(10) 0.01354(17) Uani 1 1 d . . .
C29 C 0.28082(11) 0.18011(4) 0.70864(11) 0.01540(18) Uani 1 1 d . . .
H29 H 0.2619 0.1778 0.7910 0.018 Uiso 1 1 calc R . .
C30 C 0.22451(11) 0.22228(4) 0.61206(11) 0.01600(19) Uani 1 1 d . . .
H30 H 0.1674 0.2479 0.6297 0.019 Uiso 1 1 calc R . .
C31 C 0.25000(10) 0.22792(4) 0.48967(11) 0.01441(18) Uani 1 1 d . . .
C32 C 0.33746(10) 0.18986(4) 0.47065(10) 0.01264(17) Uani 1 1 d . . .
C33 C 0.42562(12) 0.09575(4) 0.79298(11) 0.01793(19) Uani 1 1 d . . .
H33A H 0.3970 0.0632 0.7366 0.027 Uiso 1 1 calc R . .
H33B H 0.3848 0.0965 0.8626 0.027 Uiso 1 1 calc R . .
H33C H 0.5348 0.0982 0.8485 0.027 Uiso 1 1 calc R . .
C34 C 0.18394(12) 0.27323(4) 0.38414(12) 0.0199(2) Uani 1 1 d . . .
H34A H 0.2634 0.2914 0.3742 0.030 Uiso 1 1 calc R . .
H34B H 0.1363 0.2972 0.4232 0.030 Uiso 1 1 calc R . .
H34C H 0.1094 0.2604 0.2865 0.030 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
C20 O1 C19 110.50(7) . . ?
C19 C1 C10 103.64(7) . . ?
C19 C1 C2 108.46(7) . . ?
C10 C1 C2 109.86(7) . . ?
C19 C1 C18 108.29(7) . . ?
C10 C1 C18 109.83(7) . . ?
C2 C1 C18 116.01(7) . . ?
C21 C2 C3 105.79(8) . . ?
C21 C2 C1 109.20(8) . . ?
C3 C2 C1 104.90(7) . . ?
C4 C3 C8 120.41(9) . . ?
C4 C3 C2 126.31(9) . . ?
C8 C3 C2 113.24(8) . . ?
C3 C4 C5 119.41(10) . . ?
C6 C5 C4 120.40(9) . . ?
C5 C6 C7 120.19(9) . . ?
C8 C7 C6 119.56(9) . . ?
C7 C8 C3 120.02(9) . . ?
C7 C8 C9 126.47(9) . . ?
C3 C8 C9 113.48(8) . . ?
C26 C9 C8 105.72(7) . . ?
C26 C9 C10 108.88(7) . . ?
C8 C9 C10 105.06(7) . . ?
C20 C10 C1 104.08(7) . . ?
C20 C10 C9 107.98(7) . . ?
C1 C10 C9 109.66(7) . . ?
C20 C10 C11 107.62(7) . . ?
C1 C10 C11 109.38(7) . . ?
C9 C10 C11 117.28(7) . . ?
C27 C11 C12 105.49(7) . . ?
C27 C11 C10 110.05(7) . . ?
C12 C11 C10 104.98(7) . . ?
C13 C12 C17 120.28(9) . . ?
C13 C12 C11 126.64(8) . . ?
C17 C12 C11 113.04(8) . . ?
C12 C13 C14 119.02(9) . . ?
C15 C14 C13 120.79(9) . . ?
C14 C15 C16 120.11(9) . . ?
C17 C16 C15 119.38(9) . . ?
C16 C17 C12 120.41(9) . . ?
C16 C17 C18 126.29(9) . . ?
C12 C17 C18 113.23(8) . . ?
C17 C18 C32 105.62(7) . . ?
C17 C18 C1 104.76(7) . . ?
C32 C18 C1 110.07(7) . . ?
O2 C19 O1 120.09(9) . . ?
O2 C19 C1 128.95(9) . . ?
O1 C19 C1 110.95(8) . . ?
O3 C20 O1 120.61(9) . . ?
O3 C20 C10 128.56(9) . . ?
O1 C20 C10 110.82(8) . . ?
C22 C21 C26 120.47(10) . . ?
C22 C21 C2 125.97(10) . . ?
C26 C21 C2 113.43(8) . . ?
C21 C22 C23 118.97(11) . . ?
C24 C23 C22 120.62(10) . . ?
C23 C24 C25 120.43(10) . . ?
C26 C25 C24 119.06(11) . . ?
C25 C26 C21 120.43(9) . . ?
C25 C26 C9 125.87(9) . . ?
C21 C26 C9 113.56(8) . . ?
C28 C27 C32 121.59(9) . . ?
C28 C27 C11 124.91(8) . . ?
C32 C27 C11 113.30(8) . . ?
C27 C28 C29 116.86(9) . . ?
C27 C28 C33 121.99(9) . . ?
C29 C28 C33 121.13(9) . . ?
C30 C29 C28 121.60(9) . . ?
C29 C30 C31 121.67(9) . . ?
C32 C31 C30 116.89(9) . . ?
C32 C31 C34 122.52(9) . . ?
C30 C31 C34 120.59(9) . . ?
C31 C32 C27 121.35(9) . . ?
C31 C32 C18 125.34(8) . . ?
C27 C32 C18 113.12(8) . . ?
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
O1 C20 1.3860(11) . ?
O1 C19 1.3891(11) . ?
O2 C19 1.1933(12) . ?
O3 C20 1.1945(12) . ?
C1 C19 1.5256(13) . ?
C1 C10 1.5496(12) . ?
C1 C2 1.5655(13) . ?
C1 C18 1.5674(13) . ?
C2 C21 1.5172(14) . ?
C2 C3 1.5211(13) . ?
C3 C4 1.3873(14) . ?
C3 C8 1.4011(13) . ?
C4 C5 1.3958(15) . ?
C5 C6 1.3896(15) . ?
C6 C7 1.3974(14) . ?
C7 C8 1.3897(13) . ?
C8 C9 1.5253(13) . ?
C9 C26 1.5140(13) . ?
C9 C10 1.5681(13) . ?
C10 C20 1.5240(13) . ?
C10 C11 1.5683(13) . ?
C11 C27 1.5202(12) . ?
C11 C12 1.5236(13) . ?
C12 C13 1.3881(13) . ?
C12 C17 1.4061(13) . ?
C13 C14 1.4002(14) . ?
C14 C15 1.3905(15) . ?
C15 C16 1.3979(14) . ?
C16 C17 1.3879(13) . ?
C17 C18 1.5194(13) . ?
C18 C32 1.5201(13) . ?
C21 C22 1.3892(14) . ?
C21 C26 1.4003(14) . ?
C22 C23 1.3969(17) . ?
C23 C24 1.3891(19) . ?
C24 C25 1.3976(15) . ?
C25 C26 1.3889(14) . ?
C27 C28 1.3968(13) . ?
C27 C32 1.4036(13) . ?
C28 C29 1.4000(13) . ?
C28 C33 1.5073(13) . ?
C29 C30 1.3934(14) . ?
C30 C31 1.4007(14) . ?
C31 C32 1.3972(13) . ?
C31 C34 1.5114(13) . ?
