#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/59/1545942.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_1545942
loop_
_publ_author_name
'Liu, Wei'
'Ren, Wenlong'
'Li, Jingfu'
'Shi, Yuan'
'Chang, Wenju'
'Shi, Yian'
_publ_section_title
;
 A Ligand-Directed Catalytic Regioselective Hydrocarboxylation of Aryl
 Olefins with Pd and Formic Acid.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1748
_journal_page_last               1751
_journal_paper_doi               10.1021/acs.orglett.7b00507
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C11 H14 O2'
_chemical_formula_weight         178.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0820(16)
_cell_length_b                   23.635(5)
_cell_length_c                   5.2570(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     986.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4001
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0591
_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)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1837
_reflns_number_gt                1175
_reflns_number_total             1827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00507_si_002.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        986.6(3)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               1545942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.2082(2) 0.51539(8) 0.6863(4) 0.0630(6) Uani 1 1 d .
H1A H 0.1392 0.5235 0.5564 0.095 Uiso 1 1 calc R
C1 C 0.3274(3) 0.38427(10) 1.4179(4) 0.0448(6) Uani 1 1 d .
O2 O 0.0087(2) 0.45450(7) 0.7423(3) 0.0564(5) Uani 1 1 d .
C2 C 0.4911(3) 0.40452(12) 1.4871(5) 0.0559(7) Uani 1 1 d .
H2A H 0.5259 0.4343 1.3940 0.067 Uiso 1 1 calc R
C3 C 0.6030(3) 0.38137(13) 1.6909(5) 0.0617(8) Uani 1 1 d .
H3A H 0.7115 0.3960 1.7330 0.074 Uiso 1 1 calc R
C4 C 0.5577(3) 0.33737(11) 1.8322(5) 0.0568(7) Uani 1 1 d .
C5 C 0.3939(3) 0.31775(12) 1.7654(5) 0.0587(7) Uani 1 1 d .
H5A H 0.3602 0.2881 1.8605 0.070 Uiso 1 1 calc R
C6 C 0.2781(3) 0.34027(10) 1.5636(5) 0.0488(6) Uani 1 1 d .
C7 C 0.6797(4) 0.31135(15) 2.0556(6) 0.0832(10) Uani 1 1 d .
H7A H 0.7862 0.3304 2.0753 0.125 Uiso 1 1 calc R
H7B H 0.6947 0.2720 2.0210 0.125 Uiso 1 1 calc R
H7C H 0.6354 0.3151 2.2120 0.125 Uiso 1 1 calc R
C8 C 0.1003(3) 0.31755(12) 1.5053(6) 0.0679(8) Uani 1 1 d .
H8A H 0.0892 0.2873 1.6229 0.102 Uiso 1 1 calc R
H8B H 0.0759 0.3036 1.3307 0.102 Uiso 1 1 calc R
H8C H 0.0227 0.3473 1.5252 0.102 Uiso 1 1 calc R
C9 C 0.2044(3) 0.40818(11) 1.1913(4) 0.0481(6) Uani 1 1 d .
H9A H 0.1641 0.3774 1.0739 0.058 Uiso 1 1 calc R
H9B H 0.1082 0.4232 1.2554 0.058 Uiso 1 1 calc R
C10 C 0.2724(3) 0.45406(11) 1.0399(4) 0.0495(6) Uani 1 1 d .
H10A H 0.3072 0.4859 1.1540 0.059 Uiso 1 1 calc R
H10B H 0.3714 0.4399 0.9811 0.059 Uiso 1 1 calc R
C11 C 0.1487(3) 0.47424(11) 0.8115(4) 0.0479(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0564(11) 0.0735(13) 0.0565(11) 0.0248(9) 0.0035(9) -0.0070(8)
C1 0.0424(13) 0.0531(14) 0.0380(13) -0.0011(11) 0.0052(10) 0.0042(10)
O2 0.0500(10) 0.0672(12) 0.0497(10) 0.0174(9) 0.0034(8) -0.0025(8)
C2 0.0463(14) 0.0697(17) 0.0513(14) 0.0106(13) 0.0078(12) 0.0007(11)
C3 0.0436(14) 0.084(2) 0.0535(15) -0.0009(15) -0.0022(12) 0.0029(12)
C4 0.0585(16) 0.0593(16) 0.0464(14) -0.0038(13) -0.0058(12) 0.0126(12)
C5 0.0647(17) 0.0526(16) 0.0543(16) 0.0093(13) -0.0008(13) 0.0012(12)
C6 0.0511(14) 0.0474(14) 0.0449(13) 0.0011(11) 0.0014(11) 0.0030(10)
C7 0.076(2) 0.093(2) 0.068(2) 0.0056(18) -0.0199(16) 0.0163(17)
C8 0.0651(17) 0.0606(17) 0.0713(19) 0.0155(15) -0.0045(14) -0.0111(13)
C9 0.0456(13) 0.0594(15) 0.0389(13) 0.0043(11) 0.0073(10) 0.0051(10)
C10 0.0479(13) 0.0602(16) 0.0411(13) 0.0055(11) 0.0102(11) 0.0040(11)
C11 0.0512(14) 0.0547(15) 0.0392(12) 0.0041(11) 0.0123(11) 0.0051(11)
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
C11 O1 H1A 109.5
C2 C1 C6 118.0(2)
C2 C1 C9 122.1(2)
C6 C1 C9 119.9(2)
C3 C2 C1 121.4(3)
C3 C2 H2A 119.3
C1 C2 H2A 119.3
C4 C3 C2 121.4(2)
C4 C3 H3A 119.3
C2 C3 H3A 119.3
C3 C4 C5 117.2(2)
C3 C4 C7 121.9(3)
C5 C4 C7 120.9(3)
C6 C5 C4 122.9(3)
C6 C5 H5A 118.5
C4 C5 H5A 118.5
C5 C6 C1 119.1(2)
C5 C6 C8 120.0(3)
C1 C6 C8 120.8(2)
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C1 115.7(2)
C10 C9 H9A 108.4
C1 C9 H9A 108.4
C10 C9 H9B 108.4
C1 C9 H9B 108.4
H9A C9 H9B 107.4
C11 C10 C9 113.5(2)
C11 C10 H10A 108.9
C9 C10 H10A 108.9
C11 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.7
O2 C11 O1 122.8(2)
O2 C11 C10 124.4(2)
O1 C11 C10 112.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.315(3)
O1 H1A 0.8200
C1 C2 1.390(3)
C1 C6 1.393(3)
C1 C9 1.512(3)
O2 C11 1.215(3)
C2 C3 1.380(4)
C2 H2A 0.9300
C3 C4 1.367(4)
C3 H3A 0.9300
C4 C5 1.385(4)
C4 C7 1.516(4)
C5 C6 1.384(3)
C5 H5A 0.9300
C6 C8 1.511(4)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.508(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.491(3)
C10 H10A 0.9700
C10 H10B 0.9700
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
C6 C1 C2 C3 1.0(4)
C9 C1 C2 C3 -178.5(2)
C1 C2 C3 C4 0.4(4)
C2 C3 C4 C5 -1.2(4)
C2 C3 C4 C7 179.7(3)
C3 C4 C5 C6 0.7(4)
C7 C4 C5 C6 179.8(2)
C4 C5 C6 C1 0.7(4)
C4 C5 C6 C8 -178.7(3)
C2 C1 C6 C5 -1.5(4)
C9 C1 C6 C5 178.1(2)
C2 C1 C6 C8 177.9(2)
C9 C1 C6 C8 -2.6(4)
C2 C1 C9 C10 1.9(3)
C6 C1 C9 C10 -177.6(2)
C1 C9 C10 C11 177.3(2)
C9 C10 C11 O2 -3.4(4)
C9 C10 C11 O1 178.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3870217
