#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/24/4022460.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_4022460
loop_
_publ_author_name
'Yoshito Terao'
'Hiroyuki Wakui'
'Michiyo Nomoto'
'Tetsuya Satoh'
'Masahiro Miura'
'Masakatsu Nomura'
_publ_section_title
;
 Palladium-Catalyzed Arylation of α,α-Disubstituted
 Arylmethanols via Cleavage of a C-C or a C-H Bond To Give Biaryls
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5236
_journal_page_last               5243
_journal_paper_doi               10.1021/jo0344034
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C29 H28 O '
_chemical_formula_sum            'C29 H28 O'
_chemical_formula_weight         392.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Mon Feb 17 01:46:16 2003'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                66.96(4)
_cell_angle_beta                 68.77(5)
_cell_angle_gamma                83.88(6)
_cell_formula_units_Z            2
_cell_length_a                   10.222(10)
_cell_length_b                   10.812(9)
_cell_length_c                   12.050(9)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    293.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_cell_volume                     1141(1)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.9409
_diffrn_measured_fraction_theta_max 0.9409
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            340
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.671
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4932
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.0408
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                3128
_reflns_number_total             4932
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0344034rom20030328_021924.cif
_cod_data_source_block           '_wakui4'
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C29 H28 O '
_cod_database_code               4022460
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_calc_flag
O(1) O 0.5441(2) 0.0648(2) 0.8611(2) 0.0626(5) Uani 1.00 d
C(1) C 0.5590(2) 0.3049(2) 0.7282(2) 0.0448(6) Uani 1.00 d
C(2) C 0.7039(2) 0.3156(2) 0.6984(2) 0.0446(6) Uani 1.00 d
C(3) C 0.8509(2) 0.1147(2) 0.6733(2) 0.0488(6) Uani 1.00 d
C(4) C 0.8552(2) 0.2016(2) 0.8307(2) 0.0496(6) Uani 1.00 d
C(5) C 0.8008(2) 0.2035(2) 0.7370(2) 0.0444(6) Uani 1.00 d
C(6) C 0.3464(3) 0.1910(3) 0.9232(3) 0.0659(8) Uani 1.00 d
C(7) C 0.7734(3) 0.4431(2) 0.6243(2) 0.0588(7) Uani 1.00 d
C(8) C 0.8081(3) 0.2266(3) 0.4652(2) 0.0620(8) Uani 1.00 d
C(9) C 0.4906(3) 0.4238(2) 0.6803(2) 0.0574(7) Uani 1.00 d
C(10) C 0.4650(2) 0.1764(2) 0.8091(2) 0.0493(6) Uani 1.00 d
C(11) C 0.9539(3) 0.0259(3) 0.7038(3) 0.0661(8) Uani 1.00 d
C(12) C 0.7373(3) -0.0061(3) 0.5848(2) 0.0617(8) Uani 1.00 d
C(13) C 0.8045(2) 0.2933(2) 0.9021(2) 0.0508(7) Uani 1.00 d
C(14) C 0.7975(2) 0.1112(2) 0.5736(2) 0.0517(7) Uani 1.00 d
C(15) C 0.5608(3) 0.5472(3) 0.6075(3) 0.0704(9) Uani 1.00 d
C(16) C 0.7029(3) 0.5581(3) 0.5797(3) 0.0670(8) Uani 1.00 d
C(17) C 0.6695(3) 0.2727(3) 0.9924(2) 0.0634(8) Uani 1.00 d
C(18) C 0.4066(3) 0.1401(3) 0.7247(3) 0.0726(10) Uani 1.00 d
C(19) C 0.6888(3) -0.0001(3) 0.4889(3) 0.0731(10) Uani 1.00 d
C(20) C 0.8907(3) 0.3973(3) 0.8818(3) 0.0700(9) Uani 1.00 d
C(21) C 0.9568(3) 0.1094(3) 0.8585(3) 0.0644(8) Uani 1.00 d
C(22) C 0.7604(3) 0.2301(3) 0.3700(3) 0.0728(9) Uani 1.00 d
C(23) C 1.0062(3) 0.0231(3) 0.7954(3) 0.0742(9) Uani 1.00 d
C(24) C 0.6984(3) 0.1155(4) 0.3839(3) 0.077(1) Uani 1.00 d
C(25) C 0.6187(4) 0.3572(4) 1.0588(3) 0.085(1) Uani 1.00 d
C(26) C 0.8350(5) 0.4806(3) 0.9517(4) 0.094(1) Uani 1.00 d
C(27) C 0.7021(5) 0.4593(4) 1.0377(4) 0.097(1) Uani 1.00 d
C(28) C 0.7210(5) -0.1372(4) 0.6970(4) 0.103(1) Uani 1.00 d
C(29) C 1.0397(5) 0.4206(5) 0.7872(5) 0.115(2) Uani 1.00 d
H(1) H 0.511(3) 0.030(3) 0.933(3) 0.0839 Uiso 1.00 calc
H(2) H 0.388(3) 0.215(3) 0.977(3) 0.0815 Uiso 1.00 calc
H(3) H 0.282(3) 0.267(3) 0.894(2) 0.0815 Uiso 1.00 calc
H(4) H 0.293(3) 0.108(3) 0.976(3) 0.0815 Uiso 1.00 calc
H(5) H 0.881(3) 0.445(2) 0.604(2) 0.0731 Uiso 1.00 calc
H(6) H 0.861(3) 0.306(3) 0.453(2) 0.0740 Uiso 1.00 calc
H(7) H 0.388(3) 0.406(2) 0.702(2) 0.0704 Uiso 1.00 calc
H(8) H 0.985(3) -0.032(3) 0.657(3) 0.0797 Uiso 1.00 calc
H(9) H 0.503(3) 0.628(3) 0.580(3) 0.0843 Uiso 1.00 calc
H(10) H 0.752(3) 0.651(3) 0.522(3) 0.0816 Uiso 1.00 calc
H(11) H 0.611(3) 0.202(3) 1.005(2) 0.0753 Uiso 1.00 calc
H(12) H 0.345(3) 0.223(3) 0.694(3) 0.0887 Uiso 1.00 calc
H(13) H 0.487(3) 0.125(3) 0.643(3) 0.0887 Uiso 1.00 calc
H(14) H 0.350(3) 0.059(3) 0.782(3) 0.0887 Uiso 1.00 calc
H(15) H 0.645(3) -0.083(3) 0.501(3) 0.0895 Uiso 1.00 calc
H(16) H 0.995(3) 0.107(2) 0.928(3) 0.0777 Uiso 1.00 calc
H(17) H 0.775(3) 0.307(3) 0.293(3) 0.0902 Uiso 1.00 calc
H(18) H 1.072(3) -0.048(3) 0.820(3) 0.0911 Uiso 1.00 calc
H(19) H 0.662(3) 0.122(3) 0.314(3) 0.0914 Uiso 1.00 calc
H(20) H 0.531(4) 0.338(3) 1.114(3) 0.1044 Uiso 1.00 calc
H(21) H 0.893(4) 0.559(4) 0.934(3) 0.1162 Uiso 1.00 calc
H(22) H 0.670(4) 0.510(4) 1.085(4) 0.1206 Uiso 1.00 calc
H(23) H 0.655(4) -0.205(4) 0.700(4) 0.1337 Uiso 1.00 calc
H(24) H 0.804(4) -0.183(4) 0.671(4) 0.1337 Uiso 1.00 calc
H(25) H 0.714(4) -0.127(4) 0.774(4) 0.1337 Uiso 1.00 calc
H(26) H 1.106(4) 0.444(4) 0.821(3) 0.1307 Uiso 1.00 calc
H(27) H 1.058(4) 0.389(4) 0.722(4) 0.1307 Uiso 1.00 calc
H(28) H 1.034(4) 0.517(4) 0.759(4) 0.1307 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C(2) C(1) C(9) 117.5(2) yes
C(2) C(1) C(10) 126.6(2) yes
C(9) C(1) C(10) 115.9(2) yes
C(1) C(2) C(5) 127.6(2) yes
C(1) C(2) C(7) 118.9(2) yes
C(5) C(2) C(7) 113.5(2) yes
C(5) C(3) C(11) 118.8(2) yes
C(5) C(3) C(14) 122.3(2) yes
C(11) C(3) C(14) 118.8(2) yes
C(5) C(4) C(13) 121.8(2) yes
C(5) C(4) C(21) 119.1(2) yes
C(13) C(4) C(21) 119.2(2) yes
C(2) C(5) C(3) 122.6(2) yes
C(2) C(5) C(4) 117.3(2) yes
C(3) C(5) C(4) 119.6(2) yes
C(2) C(7) C(16) 122.2(2) yes
C(14) C(8) C(22) 122.5(3) yes
C(1) C(9) C(15) 122.6(3) yes
O(1) C(10) C(1) 110.7(2) yes
O(1) C(10) C(6) 106.6(2) yes
O(1) C(10) C(18) 107.2(2) yes
C(1) C(10) C(6) 111.5(2) yes
C(1) C(10) C(18) 110.0(2) yes
C(6) C(10) C(18) 110.7(2) yes
C(3) C(11) C(23) 121.7(2) yes
C(14) C(12) C(19) 118.7(3) yes
C(14) C(12) C(28) 122.8(3) yes
C(19) C(12) C(28) 118.5(3) yes
C(4) C(13) C(17) 119.2(2) yes
C(4) C(13) C(20) 121.4(2) yes
C(17) C(13) C(20) 119.4(2) yes
C(3) C(14) C(8) 119.7(2) yes
C(3) C(14) C(12) 122.5(2) yes
C(8) C(14) C(12) 117.8(2) yes
C(9) C(15) C(16) 120.0(3) yes
C(7) C(16) C(15) 118.9(2) yes
C(13) C(17) C(25) 120.5(3) yes
C(12) C(19) C(24) 122.4(3) yes
C(13) C(20) C(26) 118.2(3) yes
C(13) C(20) C(29) 121.1(3) yes
C(26) C(20) C(29) 120.7(3) yes
C(4) C(21) C(23) 121.2(2) yes
C(8) C(22) C(24) 119.0(3) yes
C(11) C(23) C(21) 119.6(2) yes
C(19) C(24) C(22) 119.6(3) yes
C(17) C(25) C(27) 119.8(3) yes
C(20) C(26) C(27) 121.0(3) yes
C(25) C(27) C(26) 121.0(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(10) 1.439(3) yes
C(1) C(2) 1.399(3) yes
C(1) C(9) 1.412(3) yes
C(1) C(10) 1.533(3) yes
C(2) C(5) 1.517(3) yes
C(2) C(7) 1.411(3) yes
C(3) C(5) 1.401(3) yes
C(3) C(11) 1.398(3) yes
C(3) C(14) 1.502(3) yes
C(4) C(5) 1.420(3) yes
C(4) C(13) 1.492(3) yes
C(4) C(21) 1.398(3) yes
C(6) C(10) 1.519(3) yes
C(7) C(16) 1.386(4) yes
C(8) C(14) 1.388(3) yes
C(8) C(22) 1.386(4) yes
C(9) C(15) 1.377(4) yes
C(10) C(18) 1.531(3) yes
C(11) C(23) 1.379(4) yes
C(12) C(14) 1.406(3) yes
C(12) C(19) 1.390(4) yes
C(12) C(28) 1.500(4) yes
C(13) C(17) 1.388(4) yes
C(13) C(20) 1.393(3) yes
C(15) C(16) 1.374(4) yes
C(17) C(25) 1.385(4) yes
C(19) C(24) 1.368(4) yes
C(20) C(26) 1.408(4) yes
C(20) C(29) 1.511(5) yes
C(21) C(23) 1.372(4) yes
C(22) C(24) 1.376(4) yes
C(25) C(27) 1.354(5) yes
C(26) C(27) 1.354(5) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(1) 2.898(4) 2_657
O(1) C(6) 3.388(4) 2_657
C(9) C(15) 3.583(4) 2_666
C(11) C(19) 3.599(5) 2_756
C(23) C(24) 3.588(4) 2_756
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
O(1) C(10) C(1) C(2) 4.5(3) yes
O(1) C(10) C(1) C(9) -175.2(2) yes
C(1) C(2) C(5) C(3) 79.3(3) yes
C(1) C(2) C(5) C(4) -108.8(2) yes
C(1) C(2) C(7) C(16) -0.3(3) yes
C(1) C(9) C(15) C(16) -0.4(4) yes
C(2) C(1) C(9) C(15) -0.5(3) yes
C(2) C(1) C(10) C(6) 122.9(2) yes
C(2) C(1) C(10) C(18) -113.9(2) yes
C(2) C(5) C(3) C(11) 171.7(2) yes
C(2) C(5) C(3) C(14) -8.5(3) yes
C(2) C(5) C(4) C(13) 8.4(3) yes
C(2) C(5) C(4) C(21) -172.9(2) yes
C(2) C(7) C(16) C(15) -0.7(4) yes
C(3) C(5) C(2) C(7) -100.9(2) yes
C(3) C(5) C(4) C(13) -179.5(2) yes
C(3) C(5) C(4) C(21) -0.8(3) yes
C(3) C(11) C(23) C(21) -0.2(5) yes
C(3) C(14) C(8) C(22) -179.7(2) yes
C(3) C(14) C(12) C(19) 179.2(2) yes
C(3) C(14) C(12) C(28) 0.1(4) yes
C(4) C(5) C(2) C(7) 71.0(2) yes
C(4) C(5) C(3) C(11) 0.0(3) yes
C(4) C(5) C(3) C(14) 179.8(2) yes
C(4) C(13) C(17) C(25) -179.1(2) yes
C(4) C(13) C(20) C(26) 179.3(2) yes
C(4) C(13) C(20) C(29) -0.6(4) yes
C(4) C(21) C(23) C(11) -0.7(4) yes
C(5) C(2) C(1) C(9) -179.4(2) yes
C(5) C(2) C(1) C(10) 0.9(3) yes
C(5) C(2) C(7) C(16) 180.0(2) yes
C(5) C(3) C(11) C(23) 0.5(4) yes
C(5) C(3) C(14) C(8) 58.1(3) yes
C(5) C(3) C(14) C(12) -122.5(2) yes
C(5) C(4) C(13) C(17) 69.9(3) yes
C(5) C(4) C(13) C(20) -111.3(3) yes
C(5) C(4) C(21) C(23) 1.2(4) yes
C(6) C(10) C(1) C(9) -56.8(3) yes
C(7) C(2) C(1) C(9) 0.8(3) yes
C(7) C(2) C(1) C(10) -178.9(2) yes
C(7) C(16) C(15) C(9) 1.0(4) yes
C(8) C(14) C(3) C(11) -122.1(3) yes
C(8) C(14) C(12) C(19) -1.4(3) yes
C(8) C(14) C(12) C(28) 179.6(3) yes
C(8) C(22) C(24) C(19) -1.9(4) yes
C(9) C(1) C(10) C(18) 66.4(3) yes
C(10) C(1) C(9) C(15) 179.2(2) yes
C(11) C(3) C(14) C(12) 57.4(3) yes
C(12) C(14) C(8) C(22) 0.8(4) yes
C(12) C(19) C(24) C(22) 1.3(4) yes
C(13) C(4) C(21) C(23) 179.9(2) yes
C(13) C(17) C(25) C(27) -1.3(5) yes
C(13) C(20) C(26) C(27) 0.9(5) yes
C(14) C(3) C(11) C(23) -179.3(3) yes
C(14) C(8) C(22) C(24) 0.9(4) yes
C(14) C(12) C(19) C(24) 0.4(4) yes
C(17) C(13) C(4) C(21) -108.8(3) yes
C(17) C(13) C(20) C(26) -1.9(4) yes
C(17) C(13) C(20) C(29) 178.2(3) yes
C(17) C(25) C(27) C(26) 0.3(5) yes
C(20) C(13) C(4) C(21) 70.0(3) yes
C(20) C(13) C(17) C(25) 2.1(4) yes
C(20) C(26) C(27) C(25) -0.1(6) yes
C(24) C(19) C(12) C(28) 179.5(3) yes
C(27) C(26) C(20) C(29) -179.2(4) yes
C(27) C(26) C(20) C(29) -179.2(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9058975
