#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/25/1502566.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_1502566
loop_
_publ_author_name
'Cammidge, Andrew N.'
'Goddard, Victoria H. M.'
'Schubert, Christopher P. J.'
'Gopee, Hemant'
'Hughes, David L.'
'Gonzalez-Lucas, Daniel'
_publ_section_title
;
 Unexpected phenol production from arylboronic acids under palladium-free
 conditions; organocatalyzed air oxidation.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6034
_journal_page_last               6037
_journal_paper_doi               10.1021/ol202500z
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C32 H36 O4'
_chemical_formula_structural     {C10H5O-OC6H13}2
_chemical_formula_sum            'C32 H36 O4'
_chemical_formula_weight         484.61
_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 and CrysAlis RED'
_cell_angle_alpha                71.587(6)
_cell_angle_beta                 82.118(5)
_cell_angle_gamma                75.890(5)
_cell_formula_units_Z            1
_cell_length_a                   5.3199(3)
_cell_length_b                   10.5254(6)
_cell_length_c                   12.2657(9)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    140(1)
_cell_volume                     630.63(7)
_computing_cell_refinement
;
 CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 
;
_computing_data_collection
;
 CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.9 
;
_computing_data_reduction
;
 CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 
;
_computing_molecular_graphics    'ORTEP (Johnson, 1971)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      140(1)
_diffrn_detector_area_resol_mean 16.0050
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3/CCD'
_diffrn_measurement_method       'Thin slice φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9785
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.032
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 
 Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'deep purple'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0414
_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)+(0.0639P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2346
_reflns_number_total             3599
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol202500z_si_001.cif
_cod_data_source_block           victg2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502566
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
C1 C 0.4710(2) 0.55733(10) 0.32871(9) 0.0176(2) Uani 1 1 d .
C2 C 0.2425(2) 0.58594(11) 0.38970(9) 0.0184(2) Uani 1 1 d .
H2 H 0.1619 0.6774 0.3799 0.022 Uiso 1 1 calc R
C3 C 0.11821(19) 0.48257(11) 0.46857(9) 0.0167(2) Uani 1 1 d .
C4 C 0.2549(2) 0.33648(11) 0.48133(9) 0.0182(2) Uani 1 1 d .
C5 C 0.6329(2) 0.17583(12) 0.42025(10) 0.0233(3) Uani 1 1 d .
H5 H 0.5625 0.1040 0.4696 0.028 Uiso 1 1 calc R
C6 C 0.8653(2) 0.14759(12) 0.35753(10) 0.0263(3) Uani 1 1 d .
H6 H 0.9510 0.0573 0.3649 0.032 Uiso 1 1 calc R
C7 C 0.9701(2) 0.25504(12) 0.28342(10) 0.0256(3) Uani 1 1 d .
H7 H 1.1262 0.2361 0.2411 0.031 Uiso 1 1 calc R
C8 C 0.8450(2) 0.38928(12) 0.27203(9) 0.0217(2) Uani 1 1 d .
H8 H 0.9167 0.4604 0.2223 0.026 Uiso 1 1 calc R
C9 C 0.6094(2) 0.41852(10) 0.33550(9) 0.0173(2) Uani 1 1 d .
C10 C 0.5031(2) 0.31063(10) 0.41020(9) 0.0179(2) Uani 1 1 d .
O1 O 0.59340(14) 0.65437(7) 0.25618(6) 0.02194(19) Uani 1 1 d .
C11 C 0.4749(2) 0.79548(11) 0.24455(9) 0.0196(2) Uani 1 1 d .
H11A H 0.4421 0.8109 0.3196 0.024 Uiso 1 1 calc R
H11B H 0.3107 0.8201 0.2091 0.024 Uiso 1 1 calc R
C12 C 0.6598(2) 0.88088(11) 0.17000(9) 0.0199(2) Uani 1 1 d .
H12A H 0.6949 0.8622 0.0962 0.024 Uiso 1 1 calc R
H12B H 0.8228 0.8551 0.2064 0.024 Uiso 1 1 calc R
C13 C 0.5501(2) 1.03324(11) 0.15069(9) 0.0198(2) Uani 1 1 d .
H13A H 0.5205 1.0519 0.2245 0.024 Uiso 1 1 calc R
H13B H 0.3837 1.0578 0.1172 0.024 Uiso 1 1 calc R
C14 C 0.7285(2) 1.12274(10) 0.07196(9) 0.0196(2) Uani 1 1 d .
H14A H 0.8897 1.1032 0.1086 0.023 Uiso 1 1 calc R
H14B H 0.7696 1.0984 0.0006 0.023 Uiso 1 1 calc R
C15 C 0.6128(2) 1.27535(11) 0.04397(10) 0.0229(2) Uani 1 1 d .
H15A H 0.5695 1.2998 0.1152 0.027 Uiso 1 1 calc R
H15B H 0.4530 1.2955 0.0061 0.027 Uiso 1 1 calc R
C16 C 0.7952(2) 1.36283(12) -0.03318(11) 0.0299(3) Uani 1 1 d .
H16A H 0.7120 1.4580 -0.0486 0.045 Uiso 1 1 calc R
H16B H 0.8369 1.3401 -0.1044 0.045 Uiso 1 1 calc R
H16C H 0.9516 1.3456 0.0048 0.045 Uiso 1 1 calc R
O4 O 0.17837(15) 0.23593(8) 0.54728(7) 0.0270(2) Uani 1 1 d .
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
C2 C1 O1 124.01(10) .
C2 C1 C9 122.67(9) .
O1 C1 C9 113.32(8) .
C1 C2 C3 123.58(10) .
C1 C2 H2 118.2 .
C3 C2 H2 118.2 .
C3 C3 C2 121.53(12) 2_566
C3 C3 C4 122.12(11) 2_566
C2 C3 C4 116.34(9) .
O4 C4 C10 117.52(10) .
O4 C4 C3 124.57(9) .
C10 C4 C3 117.91(8) .
C6 C5 C10 120.71(10) .
C6 C5 H5 119.6 .
C10 C5 H5 119.6 .
C5 C6 C7 119.61(11) .
C5 C6 H6 120.2 .
C7 C6 H6 120.2 .
C8 C7 C6 120.68(10) .
C8 C7 H7 119.7 .
C6 C7 H7 119.7 .
C7 C8 C9 119.96(10) .
C7 C8 H8 120.0 .
C9 C8 H8 120.0 .
C10 C9 C8 119.55(10) .
C10 C9 C1 117.89(9) .
C8 C9 C1 122.55(9) .
C5 C10 C9 119.49(10) .
C5 C10 C4 118.92(9) .
C9 C10 C4 121.58(9) .
C1 O1 C11 117.89(8) .
O1 C11 C12 107.57(8) .
O1 C11 H11A 110.2 .
C12 C11 H11A 110.2 .
O1 C11 H11B 110.2 .
C12 C11 H11B 110.2 .
H11A C11 H11B 108.5 .
C11 C12 C13 111.80(8) .
C11 C12 H12A 109.3 .
C13 C12 H12A 109.3 .
C11 C12 H12B 109.3 .
C13 C12 H12B 109.3 .
H12A C12 H12B 107.9 .
C12 C13 C14 113.09(8) .
C12 C13 H13A 109.0 .
C14 C13 H13A 109.0 .
C12 C13 H13B 109.0 .
C14 C13 H13B 109.0 .
H13A C13 H13B 107.8 .
C15 C14 C13 113.81(8) .
C15 C14 H14A 108.8 .
C13 C14 H14A 108.8 .
C15 C14 H14B 108.8 .
C13 C14 H14B 108.8 .
H14A C14 H14B 107.7 .
C14 C15 C16 112.99(9) .
C14 C15 H15A 109.0 .
C16 C15 H15A 109.0 .
C14 C15 H15B 109.0 .
C16 C15 H15B 109.0 .
H15A C15 H15B 107.8 .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3574(14) .
C1 O1 1.3602(11) .
C1 C9 1.4490(14) .
C2 C3 1.4377(13) .
C2 H2 0.9300 .
C3 C3 1.4137(19) 2_566
C3 C4 1.5007(14) .
C4 O4 1.2326(12) .
C4 C10 1.4957(14) .
C5 C6 1.3832(15) .
C5 C10 1.3929(14) .
C5 H5 0.9300 .
C6 C7 1.3912(15) .
C6 H6 0.9300 .
C7 C8 1.3788(15) .
C7 H7 0.9300 .
C8 C9 1.4023(14) .
C8 H8 0.9300 .
C9 C10 1.4010(14) .
O1 C11 1.4346(12) .
C11 C12 1.5089(14) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.5199(14) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.5264(14) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.5180(14) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.5225(15) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9913220
