#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:03:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178766 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/20/4102038.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_4102038
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            'C35 H26 Cl2 O3'
_chemical_formula_weight         565.46
_chemical_name_systematic
;
 ?
;
_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           SHELXL-97
_cell_angle_alpha                87.0830(10)
_cell_angle_beta                 83.0080(10)
_cell_angle_gamma                82.6520(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4171(3)
_cell_length_b                   10.5841(3)
_cell_length_c                   13.7962(4)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    142(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1352.78(7)
_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      142(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30197
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9597
_exptl_absorpt_correction_T_min  0.8740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         7564
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.6085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                6485
_reflns_number_total             7564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja903653j_si_005.cif
_cod_data_source_block           07057
_cod_database_code               4102038
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.15044(9) 0.51136(9) 0.21926(7) 0.02402(19) Uani 1 1 d . . .
C1 C 0.27951(12) 0.30395(11) 0.24621(8) 0.0174(2) Uani 1 1 d . . .
O2 O 0.02178(10) 0.36377(10) 0.29664(7) 0.0298(2) Uani 1 1 d . . .
C2 C 0.26556(13) 0.18974(11) 0.18110(9) 0.0206(2) Uani 1 1 d . . .
H2 H 0.2013 0.1292 0.2154 0.025 Uiso 1 1 calc R . .
O3 O 0.32589(11) 0.61595(9) 0.14078(7) 0.0278(2) Uani 1 1 d . . .
C3 C 0.20638(13) 0.25335(12) 0.09012(9) 0.0219(2) Uani 1 1 d . . .
C4 C 0.07419(14) 0.24100(14) 0.05851(10) 0.0277(3) Uani 1 1 d . . .
H4 H 0.0111 0.1870 0.0937 0.033 Uiso 1 1 calc R . .
C5 C 0.03552(15) 0.30933(15) -0.02594(11) 0.0330(3) Uani 1 1 d . . .
H5 H -0.0541 0.3009 -0.0485 0.040 Uiso 1 1 calc R . .
C6 C 0.12638(16) 0.38883(15) -0.07684(10) 0.0325(3) Uani 1 1 d . . .
H6 H 0.0993 0.4339 -0.1344 0.039 Uiso 1 1 calc R . .
C7 C 0.25782(15) 0.40325(13) -0.04401(9) 0.0270(3) Uani 1 1 d . . .
H7 H 0.3194 0.4592 -0.0782 0.032 Uiso 1 1 calc R . .
C8 C 0.29753(13) 0.33492(12) 0.03914(8) 0.0209(2) Uani 1 1 d . . .
C9 C 0.43552(12) 0.34064(11) 0.08541(8) 0.0185(2) Uani 1 1 d . . .
H9 H 0.5009 0.3964 0.0461 0.022 Uiso 1 1 calc R . .
C10 C 0.38434(12) 0.39160(10) 0.19050(8) 0.0164(2) Uani 1 1 d . . .
C11 C 0.50306(12) 0.41158(10) 0.25662(8) 0.0168(2) Uani 1 1 d . . .
H11 H 0.5746 0.4661 0.2228 0.020 Uiso 1 1 calc R . .
C12 C 0.42014(12) 0.47317(11) 0.34802(8) 0.0174(2) Uani 1 1 d . . .
C13 C 0.43538(13) 0.59324(11) 0.38028(9) 0.0212(2) Uani 1 1 d . . .
C14 C 0.35030(14) 0.63229(12) 0.46688(9) 0.0248(2) Uani 1 1 d . . .
H14 H 0.3592 0.7125 0.4919 0.030 Uiso 1 1 calc R . .
C15 C 0.25374(13) 0.55650(13) 0.51661(9) 0.0252(3) Uani 1 1 d . . .
H15 H 0.1975 0.5866 0.5746 0.030 Uiso 1 1 calc R . .
C16 C 0.23669(12) 0.43697(12) 0.48392(9) 0.0223(2) Uani 1 1 d . . .
C17 C 0.32302(12) 0.39602(11) 0.39882(8) 0.0181(2) Uani 1 1 d . . .
C18 C 0.32398(12) 0.26878(11) 0.35101(8) 0.0185(2) Uani 1 1 d . . .
H18 H 0.2573 0.2136 0.3896 0.022 Uiso 1 1 calc R . .
C19 C 0.13590(12) 0.38909(12) 0.25870(9) 0.0219(2) Uani 1 1 d . . .
C20 C 0.29152(13) 0.51879(11) 0.17880(8) 0.0205(2) Uani 1 1 d . . .
C21 C 0.41522(13) 0.12377(11) 0.14713(9) 0.0222(2) Uani 1 1 d . . .
C22 C 0.46409(17) -0.00461(13) 0.15928(10) 0.0303(3) Uani 1 1 d . . .
H22 H 0.4033 -0.0607 0.1942 0.036 Uiso 1 1 calc R . .
C23 C 0.60395(18) -0.05083(14) 0.11963(11) 0.0359(3) Uani 1 1 d . . .
H23 H 0.6381 -0.1386 0.1281 0.043 Uiso 1 1 calc R . .
C24 C 0.69296(16) 0.03010(15) 0.06823(11) 0.0342(3) Uani 1 1 d . . .
H24 H 0.7876 -0.0025 0.0416 0.041 Uiso 1 1 calc R . .
C25 C 0.64436(14) 0.15940(13) 0.05536(9) 0.0268(3) Uani 1 1 d . . .
H25 H 0.7050 0.2152 0.0200 0.032 Uiso 1 1 calc R . .
C26 C 0.50575(13) 0.20507(11) 0.09519(8) 0.0204(2) Uani 1 1 d . . .
C27 C 0.57522(12) 0.28406(11) 0.29121(8) 0.0184(2) Uani 1 1 d . . .
C28 C 0.72264(13) 0.24573(13) 0.28241(9) 0.0247(2) Uani 1 1 d . . .
H28 H 0.7879 0.2977 0.2473 0.030 Uiso 1 1 calc R . .
C29 C 0.77338(15) 0.12967(14) 0.32597(11) 0.0324(3) Uani 1 1 d . . .
H29 H 0.8742 0.1034 0.3218 0.039 Uiso 1 1 calc R . .
C30 C 0.67816(17) 0.05238(13) 0.37527(11) 0.0338(3) Uani 1 1 d . . .
H30 H 0.7142 -0.0272 0.4036 0.041 Uiso 1 1 calc R . .
C31 C 0.52944(15) 0.09025(12) 0.38374(9) 0.0268(3) Uani 1 1 d . . .
H31 H 0.4642 0.0369 0.4172 0.032 Uiso 1 1 calc R . .
C32 C 0.47883(12) 0.20721(11) 0.34235(8) 0.0195(2) Uani 1 1 d . . .
C33 C 0.53824(16) 0.67757(13) 0.32571(10) 0.0295(3) Uani 1 1 d . . .
H33A H 0.6369 0.6342 0.3231 0.044 Uiso 1 1 calc R . .
H33B H 0.5316 0.7577 0.3595 0.044 Uiso 1 1 calc R . .
H33C H 0.5130 0.6956 0.2591 0.044 Uiso 1 1 calc R . .
C34 C 0.13030(14) 0.35671(15) 0.53927(10) 0.0303(3) Uani 1 1 d . . .
H34A H 0.0790 0.4032 0.5953 0.045 Uiso 1 1 calc R . .
H34B H 0.1818 0.2767 0.5624 0.045 Uiso 1 1 calc R . .
H34C H 0.0610 0.3381 0.4961 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.13565(7) 0.92637(5) 0.39479(4) 0.06303(17) Uani 1 1 d DU A .
C1S C 0.13662(19) 0.81300(16) 0.30695(14) 0.0419(4) Uani 1 1 d DU . .
H1SA H 0.0823 0.7430 0.3351 0.050 Uiso 0.425(12) 1 calc PR A 1
H1SB H 0.2369 0.7763 0.2855 0.050 Uiso 0.425(12) 1 calc PR A 1
H1SC H 0.2304 0.8060 0.2652 0.050 Uiso 0.575(12) 1 calc PR A 2
H1SD H 0.1265 0.7289 0.3401 0.050 Uiso 0.575(12) 1 calc PR A 2
Cl2 Cl 0.0536(7) 0.8899(5) 0.2033(5) 0.0728(14) Uani 0.425(12) 1 d PDU A 1
Cl2A Cl -0.0006(5) 0.8514(4) 0.2343(2) 0.0636(10) Uani 0.575(12) 1 d PDU A 2
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'
Cl Cl 0.1484 0.1585 '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 110.34(9) . . ?
C19 C1 C10 103.67(9) . . ?
C19 C1 C18 107.21(9) . . ?
C10 C1 C18 109.79(9) . . ?
C19 C1 C2 109.03(9) . . ?
C10 C1 C2 109.68(9) . . ?
C18 C1 C2 116.63(9) . . ?
C21 C2 C3 106.29(10) . . ?
C21 C2 C1 109.26(9) . . ?
C3 C2 C1 104.24(9) . . ?
C4 C3 C8 120.22(12) . . ?
C4 C3 C2 126.69(12) . . ?
C8 C3 C2 113.04(10) . . ?
C3 C4 C5 119.00(13) . . ?
C6 C5 C4 120.71(12) . . ?
C5 C6 C7 120.30(13) . . ?
C8 C7 C6 119.32(13) . . ?
C7 C8 C3 120.42(11) . . ?
C7 C8 C9 126.08(11) . . ?
C3 C8 C9 113.48(10) . . ?
C26 C9 C8 106.47(9) . . ?
C26 C9 C10 108.62(9) . . ?
C8 C9 C10 105.28(9) . . ?
C20 C10 C1 104.20(9) . . ?
C20 C10 C11 107.82(9) . . ?
C1 C10 C11 109.18(9) . . ?
C20 C10 C9 107.54(9) . . ?
C1 C10 C9 109.48(9) . . ?
C11 C10 C9 117.75(9) . . ?
C27 C11 C12 105.77(9) . . ?
C27 C11 C10 110.18(9) . . ?
C12 C11 C10 104.89(8) . . ?
C13 C12 C17 121.70(10) . . ?
C13 C12 C11 125.41(10) . . ?
C17 C12 C11 112.89(9) . . ?
C12 C13 C14 116.74(11) . . ?
C12 C13 C33 122.17(11) . . ?
C14 C13 C33 121.08(11) . . ?
C15 C14 C13 121.52(11) . . ?
C14 C15 C16 121.95(11) . . ?
C17 C16 C15 117.00(11) . . ?
C17 C16 C34 122.17(11) . . ?
C15 C16 C34 120.83(11) . . ?
C16 C17 C12 121.06(11) . . ?
C16 C17 C18 125.91(11) . . ?
C12 C17 C18 113.03(9) . . ?
C32 C18 C17 105.83(9) . . ?
C32 C18 C1 109.23(9) . . ?
C17 C18 C1 105.50(9) . . ?
O2 C19 O1 120.30(11) . . ?
O2 C19 C1 128.77(12) . . ?
O1 C19 C1 110.92(10) . . ?
O3 C20 O1 120.61(11) . . ?
O3 C20 C10 128.54(11) . . ?
O1 C20 C10 110.85(10) . . ?
C22 C21 C26 119.69(12) . . ?
C22 C21 C2 126.75(12) . . ?
C26 C21 C2 113.51(10) . . ?
C21 C22 C23 119.35(14) . . ?
C24 C23 C22 120.68(13) . . ?
C23 C24 C25 120.31(13) . . ?
C26 C25 C24 118.86(13) . . ?
C25 C26 C21 121.11(11) . . ?
C25 C26 C9 125.49(11) . . ?
C21 C26 C9 113.37(10) . . ?
C28 C27 C32 120.65(11) . . ?
C28 C27 C11 125.75(11) . . ?
C32 C27 C11 113.41(9) . . ?
C27 C28 C29 118.92(13) . . ?
C30 C29 C28 120.59(12) . . ?
C29 C30 C31 120.67(12) . . ?
C32 C31 C30 118.84(13) . . ?
C31 C32 C27 120.32(11) . . ?
C31 C32 C18 126.38(11) . . ?
C27 C32 C18 113.21(10) . . ?
Cl2A C1S Cl1 112.20(11) . . ?
Cl2A C1S Cl2 24.88(11) . . ?
Cl1 C1S Cl2 108.74(11) . . ?
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 1.3872(15) . ?
O1 C19 1.3947(16) . ?
C1 C19 1.5225(16) . ?
C1 C10 1.5501(15) . ?
C1 C18 1.5676(15) . ?
C1 C2 1.5700(16) . ?
O2 C19 1.1930(15) . ?
C2 C21 1.5213(17) . ?
C2 C3 1.5257(17) . ?
O3 C20 1.1943(15) . ?
C3 C4 1.3916(17) . ?
C3 C8 1.3991(18) . ?
C4 C5 1.401(2) . ?
C5 C6 1.382(2) . ?
C6 C7 1.3973(19) . ?
C7 C8 1.3892(17) . ?
C8 C9 1.5250(16) . ?
C9 C26 1.5080(16) . ?
C9 C10 1.5711(15) . ?
C10 C20 1.5210(15) . ?
C10 C11 1.5669(15) . ?
C11 C27 1.5132(15) . ?
C11 C12 1.5292(15) . ?
C12 C13 1.3977(16) . ?
C12 C17 1.4040(16) . ?
C13 C14 1.4046(17) . ?
C13 C33 1.5089(18) . ?
C14 C15 1.3856(19) . ?
C15 C16 1.3990(18) . ?
C16 C17 1.3987(16) . ?
C16 C34 1.5080(18) . ?
C17 C18 1.5280(16) . ?
C18 C32 1.5125(16) . ?
C21 C22 1.3863(17) . ?
C21 C26 1.3988(17) . ?
C22 C23 1.400(2) . ?
C23 C24 1.384(2) . ?
C24 C25 1.396(2) . ?
C25 C26 1.3894(17) . ?
C27 C28 1.3880(16) . ?
C27 C32 1.3992(16) . ?
C28 C29 1.3938(19) . ?
C29 C30 1.385(2) . ?
C30 C31 1.399(2) . ?
C31 C32 1.3890(16) . ?
Cl1 C1S 1.7468(18) . ?
C1S Cl2A 1.725(3) . ?
C1S Cl2 1.819(5) . ?
