#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/27/4112752.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_4112752
loop_
_publ_author_name
'Hiroyuki Wakui'
'Satoshi Kawasaki'
'Tetsuya Satoh'
'Masahiro Miura'
'Masakatsu Nomura'
_publ_section_title
;
 Palladium-Catalyzed Reaction of 2-Hydroxy-2-methylpropiophenone with Aryl
 Bromides: A Unique Multiple Arylation via Successive C-C and C-H Bond
 Cleavages
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8658
_journal_page_last               8659
_journal_paper_doi               10.1021/ja0477874
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C27 H20 O2 '
_chemical_formula_sum            'C27 H20 O2'
_chemical_formula_weight         376.45
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.827(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8736(9)
_cell_length_b                   13.7378(8)
_cell_length_c                   17.1988(9)
_cell_measurement_reflns_used    13161
_cell_measurement_temperature    223.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     3966.2(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_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 8.00
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18559
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.69
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.577
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4538
_refine_ls_R_factor_gt           0.0968
_refine_ls_shift/su_max          0.0039
_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         0.1871
_reflns_number_gt                2440
_reflns_number_total             4538
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0477874si20040417_021223.cif
_cod_data_source_block           wak
_cod_original_formula_sum        'C27 H20 O2 '
_cod_database_code               4112752
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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 0.6362(1) -0.0342(2) 0.0430(1) 0.0489(7) Uani 1.00 d
O(2) O 0.5898(2) 0.1073(2) 0.0006(1) 0.0575(8) Uani 1.00 d
C(1) C 0.6463(2) -0.0635(2) 0.1827(2) 0.0390(9) Uani 1.00 d
C(2) C 0.6246(2) 0.0618(2) 0.0531(2) 0.0445(10) Uani 1.00 d
C(3) C 0.6295(2) -0.1316(2) 0.2383(2) 0.048(1) Uani 1.00 d
C(4) C 0.7497(2) 0.1116(2) 0.1314(2) 0.0415(9) Uani 1.00 d
C(5) C 0.6367(2) 0.0357(2) 0.1963(1) 0.0388(9) Uani 1.00 d
C(6) C 0.6106(2) 0.0658(2) 0.2666(2) 0.0453(10) Uani 1.00 d
C(7) C 0.6590(2) 0.1057(2) 0.1326(2) 0.0391(9) Uani 1.00 d
C(8) C 0.6784(2) -0.0912(2) 0.1070(2) 0.0432(9) Uani 1.00 d
C(9) C 0.6241(2) 0.2077(2) 0.1424(2) 0.0425(10) Uani 1.00 d
C(10) C 0.8003(2) 0.0992(3) 0.1992(2) 0.054(1) Uani 1.00 d
C(11) C 0.6699(2) -0.1971(2) 0.0850(2) 0.0435(10) Uani 1.00 d
C(12) C 0.7839(2) 0.1368(3) 0.0636(2) 0.052(1) Uani 1.00 d
C(13) C 0.5953(2) -0.0021(3) 0.3228(2) 0.050(1) Uani 1.00 d
C(14) C 0.5419(2) 0.2198(3) 0.1363(2) 0.053(1) Uani 1.00 d
C(15) C 0.7351(2) -0.2576(3) 0.0995(2) 0.054(1) Uani 1.00 d
C(16) C 0.5979(2) -0.2347(3) 0.0517(2) 0.056(1) Uani 1.00 d
C(17) C 0.5921(3) -0.3323(3) 0.0332(2) 0.065(1) Uani 1.00 d
C(18) C 0.6710(2) 0.2880(3) 0.1597(2) 0.056(1) Uani 1.00 d
C(19) C 0.6039(2) -0.0994(3) 0.3087(2) 0.052(1) Uani 1.00 d
C(20) C 0.7287(3) -0.3556(3) 0.0811(2) 0.066(1) Uani 1.00 d
C(21) C 0.6571(3) -0.3924(3) 0.0481(2) 0.068(1) Uani 1.00 d
C(22) C 0.8644(3) 0.1490(3) 0.0640(2) 0.063(1) Uani 1.00 d
C(23) C 0.9139(2) 0.1361(3) 0.1321(3) 0.067(1) Uani 1.00 d
C(24) C 0.5565(3) 0.3891(3) 0.1636(2) 0.076(2) Uani 1.00 d
C(25) C 0.8812(2) 0.1119(3) 0.2006(2) 0.062(1) Uani 1.00 d
C(26) C 0.5090(3) 0.3100(3) 0.1479(2) 0.068(1) Uani 1.00 d
C(27) C 0.6380(3) 0.3784(3) 0.1703(2) 0.076(2) Uani 1.00 d
H(1) H 0.6352 -0.2006 0.2281 0.0576 Uiso 1.00 calc
H(2) H 0.6034 0.1355 0.2757 0.0558 Uiso 1.00 calc
H(3) H 0.7779 0.0816 0.2473 0.0659 Uiso 1.00 calc
H(4) H 0.7493 0.1455 0.0153 0.0634 Uiso 1.00 calc
H(5) H 0.5787 0.0191 0.3722 0.0612 Uiso 1.00 calc
H(6) H 0.5069 0.1636 0.1239 0.0643 Uiso 1.00 calc
H(7) H 0.7862 -0.2292 0.1222 0.0677 Uiso 1.00 calc
H(8) H 0.5520 -0.1913 0.0411 0.0704 Uiso 1.00 calc
H(9) H 0.5403 -0.3593 0.0091 0.0834 Uiso 1.00 calc
H(10) H 0.7292 0.2812 0.1637 0.0710 Uiso 1.00 calc
H(11) H 0.5931 -0.1462 0.3480 0.0624 Uiso 1.00 calc
H(12) H 0.7746 -0.3998 0.0913 0.0835 Uiso 1.00 calc
H(13) H 0.6517 -0.4618 0.0354 0.0835 Uiso 1.00 calc
H(14) H 0.8866 0.1663 0.0163 0.0762 Uiso 1.00 calc
H(15) H 0.9713 0.1438 0.1323 0.0803 Uiso 1.00 calc
H(16) H 0.5340 0.4532 0.1714 0.0911 Uiso 1.00 calc
H(17) H 0.9157 0.1018 0.2487 0.0771 Uiso 1.00 calc
H(18) H 0.4512 0.3169 0.1453 0.0824 Uiso 1.00 calc
H(19) H 0.6715 0.4346 0.1829 0.0906 Uiso 1.00 calc
H(20) H 0.7350 -0.0734 0.1105 0.0547 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) O(1) C(8) 119.3(2) yes
C(3) C(1) C(5) 120.5(3) yes
C(3) C(1) C(8) 122.8(3) yes
C(5) C(1) C(8) 116.7(3) yes
O(1) C(2) O(2) 118.6(3) yes
O(1) C(2) C(7) 116.6(3) yes
O(2) C(2) C(7) 124.8(3) yes
C(1) C(3) C(19) 119.1(3) yes
C(7) C(4) C(10) 120.9(3) yes
C(7) C(4) C(12) 121.4(3) yes
C(10) C(4) C(12) 117.6(3) yes
C(1) C(5) C(6) 119.3(3) yes
C(1) C(5) C(7) 116.8(2) yes
C(6) C(5) C(7) 123.8(3) yes
C(5) C(6) C(13) 120.3(3) yes
C(2) C(7) C(4) 107.0(2) yes
C(2) C(7) C(5) 106.8(3) yes
C(2) C(7) C(9) 109.7(3) yes
C(4) C(7) C(5) 111.1(2) yes
C(4) C(7) C(9) 110.3(3) yes
C(5) C(7) C(9) 111.7(2) yes
O(1) C(8) C(1) 108.8(3) yes
O(1) C(8) C(11) 107.4(2) yes
C(1) C(8) C(11) 115.3(3) yes
C(7) C(9) C(14) 119.5(3) yes
C(7) C(9) C(18) 122.5(3) yes
C(14) C(9) C(18) 117.9(3) yes
C(4) C(10) C(25) 121.7(3) yes
C(8) C(11) C(15) 118.8(3) yes
C(8) C(11) C(16) 121.3(3) yes
C(15) C(11) C(16) 119.9(3) yes
C(4) C(12) C(22) 121.3(3) yes
C(6) C(13) C(19) 120.1(3) yes
C(9) C(14) C(26) 120.6(4) yes
C(11) C(15) C(20) 120.1(4) yes
C(11) C(16) C(17) 119.6(4) yes
C(16) C(17) C(21) 120.3(4) yes
C(9) C(18) C(27) 121.4(4) yes
C(3) C(19) C(13) 120.7(3) yes
C(15) C(20) C(21) 119.7(4) yes
C(17) C(21) C(20) 120.3(4) yes
C(12) C(22) C(23) 120.3(3) yes
C(22) C(23) C(25) 119.4(4) yes
C(26) C(24) C(27) 119.6(4) yes
C(10) C(25) C(23) 119.7(3) yes
C(14) C(26) C(24) 120.6(4) yes
C(18) C(27) C(24) 119.9(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.347(4) yes
O(1) C(8) 1.475(4) yes
O(2) C(2) 1.201(4) yes
C(1) C(3) 1.388(4) yes
C(1) C(5) 1.394(4) yes
C(1) C(8) 1.508(4) yes
C(2) C(7) 1.552(4) yes
C(3) C(19) 1.397(4) yes
C(4) C(7) 1.536(4) yes
C(4) C(10) 1.383(4) yes
C(4) C(12) 1.396(4) yes
C(5) C(6) 1.390(4) yes
C(5) C(7) 1.533(4) yes
C(6) C(13) 1.386(4) yes
C(7) C(9) 1.536(4) yes
C(8) C(11) 1.507(4) yes
C(9) C(14) 1.389(5) yes
C(9) C(18) 1.373(4) yes
C(10) C(25) 1.373(5) yes
C(11) C(15) 1.381(5) yes
C(11) C(16) 1.390(5) yes
C(12) C(22) 1.368(5) yes
C(13) C(19) 1.369(5) yes
C(14) C(26) 1.380(5) yes
C(15) C(20) 1.384(5) yes
C(16) C(17) 1.378(5) yes
C(17) C(21) 1.376(6) yes
C(18) C(27) 1.380(5) yes
C(20) C(21) 1.378(6) yes
C(22) C(23) 1.379(5) yes
C(23) C(25) 1.391(5) yes
C(24) C(26) 1.361(6) yes
C(24) C(27) 1.377(6) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(2) C(19) 3.335(4) 4_554
O(2) C(13) 3.392(4) 4_554
C(11) C(20) 3.551(5) 7_645
C(15) C(15) 3.515(7) 7_645
C(15) C(20) 3.581(5) 7_645
C(17) C(26) 3.410(6) 3_655
C(26) C(26) 3.556(8) 2_655
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(2) C(7) C(4) 73.7(3) yes
O(1) C(2) C(7) C(5) -45.4(4) yes
O(1) C(2) C(7) C(9) -166.6(3) yes
O(1) C(8) C(1) C(3) 136.9(3) yes
O(1) C(8) C(1) C(5) -45.4(4) yes
O(1) C(8) C(11) C(15) 138.4(3) yes
O(1) C(8) C(11) C(16) -42.5(4) yes
O(2) C(2) O(1) C(8) -179.7(3) yes
O(2) C(2) C(7) C(4) -105.3(4) yes
O(2) C(2) C(7) C(5) 135.6(3) yes
O(2) C(2) C(7) C(9) 14.4(5) yes
C(1) C(3) C(19) C(13) 0.0(6) yes
C(1) C(5) C(6) C(13) 0.7(5) yes
C(1) C(5) C(7) C(2) 43.7(4) yes
C(1) C(5) C(7) C(4) -72.7(4) yes
C(1) C(5) C(7) C(9) 163.6(3) yes
C(1) C(8) O(1) C(2) 44.8(4) yes
C(1) C(8) C(11) C(15) -100.2(4) yes
C(1) C(8) C(11) C(16) 79.0(4) yes
C(2) O(1) C(8) C(11) 170.2(3) yes
C(2) C(7) C(4) C(10) -146.9(3) yes
C(2) C(7) C(4) C(12) 37.9(4) yes
C(2) C(7) C(5) C(6) -138.7(3) yes
C(2) C(7) C(9) C(14) 55.4(3) yes
C(2) C(7) C(9) C(18) -127.0(3) yes
C(3) C(1) C(5) C(6) 0.6(5) yes
C(3) C(1) C(5) C(7) 178.3(3) yes
C(3) C(1) C(8) C(11) 16.3(5) yes
C(3) C(19) C(13) C(6) 1.3(6) yes
C(4) C(7) C(5) C(6) 104.8(4) yes
C(4) C(7) C(9) C(14) 173.0(3) yes
C(4) C(7) C(9) C(18) -9.3(4) yes
C(4) C(10) C(25) C(23) -1.1(6) yes
C(4) C(12) C(22) C(23) 0.2(6) yes
C(5) C(1) C(3) C(19) -1.0(5) yes
C(5) C(1) C(8) C(11) -166.0(3) yes
C(5) C(6) C(13) C(19) -1.6(6) yes
C(5) C(7) C(4) C(10) -30.7(4) yes
C(5) C(7) C(4) C(12) 154.2(3) yes
C(5) C(7) C(9) C(14) -62.8(4) yes
C(5) C(7) C(9) C(18) 114.8(3) yes
C(6) C(5) C(1) C(8) -177.2(3) yes
C(6) C(5) C(7) C(9) -18.8(4) yes
C(7) C(2) O(1) C(8) 1.3(4) yes
C(7) C(4) C(10) C(25) -174.8(3) yes
C(7) C(4) C(12) C(22) 175.2(3) yes
C(7) C(5) C(1) C(8) 0.5(4) yes
C(7) C(5) C(6) C(13) -176.8(3) yes
C(7) C(9) C(14) C(26) 177.4(3) yes
C(7) C(9) C(18) C(27) -178.2(3) yes
C(8) C(1) C(3) C(19) 176.7(3) yes
C(8) C(11) C(15) C(20) 178.9(3) yes
C(8) C(11) C(16) C(17) -179.2(3) yes
C(9) C(7) C(4) C(10) 93.8(4) yes
C(9) C(7) C(4) C(12) -81.3(4) yes
C(9) C(14) C(26) C(24) 1.5(6) yes
C(9) C(18) C(27) C(24) 0.1(6) yes
C(10) C(4) C(12) C(22) -0.1(5) yes
C(10) C(25) C(23) C(22) 1.2(6) yes
C(11) C(15) C(20) C(21) 0.2(5) yes
C(11) C(16) C(17) C(21) 0.4(5) yes
C(12) C(4) C(10) C(25) 0.5(5) yes
C(12) C(22) C(23) C(25) -0.8(6) yes
C(14) C(9) C(18) C(27) -0.5(5) yes
C(14) C(26) C(24) C(27) -1.9(6) yes
C(15) C(11) C(16) C(17) -0.1(5) yes
C(15) C(20) C(21) C(17) 0.1(6) yes
C(16) C(11) C(15) C(20) -0.3(5) yes
C(16) C(17) C(21) C(20) -0.5(6) yes
C(18) C(9) C(14) C(26) -0.3(5) yes
C(18) C(27) C(24) C(26) 1.1(7) yes
C(18) C(27) C(24) C(26) 1.1(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139119183
