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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/48/1554838.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_1554838
loop_
_publ_author_name
'Liu, Rui'
'Lu, Ze-Hai'
'Hu, Xiao-Hui'
'Li, Jun-Li'
'Yang, Xian-Jin'
_publ_section_title
;
 Monocarboxylation and intramolecular coupling of butenylated arenes via
 palladium-catalyzed C-H activation process.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1489
_journal_page_last               1492
_journal_paper_doi               10.1021/acs.orglett.5b00376
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.008(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0260(15)
_cell_length_b                   8.7035(9)
_cell_length_c                   12.0599(12)
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.774
_cell_measurement_theta_min      5.556
_cell_volume                     1428.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8430
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.778
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0729P)²+0.0193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1469
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1831
_reflns_number_total             2807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b00376_si_002.cif
_cod_data_source_block           cd214686
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554838
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.20128(9) 0.46208(15) 0.44968(11) 0.0777(4) Uani 1 1 d . .
O2 O 0.27528(9) 0.26780(16) 0.38541(10) 0.0846(5) Uani 1 1 d . .
C1 C 0.50502(12) 0.12676(19) 0.66279(14) 0.0583(5) Uani 1 1 d . .
C2 C 0.58169(15) 0.0829(2) 0.75353(15) 0.0722(6) Uani 1 1 d . .
H2 H 0.5686 0.0164 0.8084 0.087 Uiso 1 1 calc R U
C3 C 0.67507(15) 0.1336(2) 0.76491(17) 0.0764(6) Uani 1 1 d . .
H3 H 0.7247 0.1019 0.8267 0.092 Uiso 1 1 calc R U
C4 C 0.69588(13) 0.2318(2) 0.68500(18) 0.0747(6) Uani 1 1 d . .
H4 H 0.7595 0.2679 0.6924 0.090 Uiso 1 1 calc R U
C5 C 0.62125(13) 0.2766(2) 0.59342(16) 0.0657(5) Uani 1 1 d . .
H5 H 0.6352 0.3433 0.5392 0.079 Uiso 1 1 calc R U
C6 C 0.52571(12) 0.22382(18) 0.58063(14) 0.0547(5) Uani 1 1 d . .
C7 C 0.44682(13) 0.2699(2) 0.47636(15) 0.0653(5) Uani 1 1 d . .
H7A H 0.4566 0.3762 0.4577 0.078 Uiso 1 1 calc R U
H7B H 0.4526 0.2070 0.4119 0.078 Uiso 1 1 calc R U
C8 C 0.34594(13) 0.2516(2) 0.49554(15) 0.0683(6) Uani 1 1 d . .
H8 H 0.3341 0.3304 0.5487 0.082 Uiso 1 1 calc R U
C9 C 0.33270(14) 0.0957(3) 0.54070(17) 0.0798(6) Uani 1 1 d . .
H9A H 0.3449 0.0184 0.4878 0.096 Uiso 1 1 calc R U
H9B H 0.2655 0.0841 0.5472 0.096 Uiso 1 1 calc R U
C10 C 0.40249(14) 0.0718(3) 0.65668(17) 0.0787(6) Uani 1 1 d . .
H10A H 0.3771 0.1256 0.7138 0.094 Uiso 1 1 calc R U
H10B H 0.4047 -0.0369 0.6751 0.094 Uiso 1 1 calc R U
C11 C 0.20373(12) 0.3698(2) 0.37700(15) 0.0560(4) Uani 1 1 d . .
C12 C 0.12687(11) 0.35253(18) 0.26862(14) 0.0543(4) Uani 1 1 d . .
C13 C 0.04280(13) 0.4404(2) 0.25299(16) 0.0691(5) Uani 1 1 d . .
H13 H 0.0368 0.5119 0.3082 0.083 Uiso 1 1 calc R U
C14 C -0.03222(14) 0.4232(2) 0.15662(17) 0.0751(6) Uani 1 1 d . .
H14 H -0.0887 0.4825 0.1481 0.090 Uiso 1 1 calc R U
C15 C -0.02545(12) 0.3203(2) 0.07275(16) 0.0641(5) Uani 1 1 d . .
C16 C 0.05953(13) 0.2343(2) 0.08798(15) 0.0677(5) Uani 1 1 d . .
H16 H 0.0661 0.1650 0.0316 0.081 Uiso 1 1 calc R U
C17 C 0.13494(13) 0.2491(2) 0.18501(15) 0.0626(5) Uani 1 1 d . .
H17 H 0.1912 0.1892 0.1939 0.075 Uiso 1 1 calc R U
C18 C -0.10819(15) 0.2986(3) -0.03210(18) 0.0874(7) Uani 1 1 d . .
H18A H -0.1271 0.3965 -0.0673 0.131 Uiso 1 1 calc R U
H18B H -0.1634 0.2528 -0.0106 0.131 Uiso 1 1 calc R U
H18C H -0.0868 0.2326 -0.0852 0.131 Uiso 1 1 calc R U
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 O2 C8 118.01(14)
C6 C1 C2 118.36(17)
C6 C1 C10 121.58(15)
C2 C1 C10 120.05(17)
C3 C2 C1 122.28(19)
C3 C2 H2 118.9
C1 C2 H2 118.9
C2 C3 C4 119.75(17)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 119.25(19)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 121.31(19)
C4 C5 H5 119.3
C6 C5 H5 119.3
C1 C6 C5 119.04(15)
C1 C6 C7 121.20(16)
C5 C6 C7 119.74(17)
C8 C7 C6 111.81(16)
C8 C7 H7A 109.3
C6 C7 H7A 109.3
C8 C7 H7B 109.3
C6 C7 H7B 109.3
H7A C7 H7B 107.9
O2 C8 C9 107.68(14)
O2 C8 C7 107.96(16)
C9 C8 C7 111.09(15)
O2 C8 H8 110.0
C9 C8 H8 110.0
C7 C8 H8 110.0
C8 C9 C10 110.67(15)
C8 C9 H9A 109.5
C10 C9 H9A 109.5
C8 C9 H9B 109.5
C10 C9 H9B 109.5
H9A C9 H9B 108.1
C1 C10 C9 113.51(17)
C1 C10 H10A 108.9
C9 C10 H10A 108.9
C1 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.7
O1 C11 O2 123.34(15)
O1 C11 C12 124.66(16)
O2 C11 C12 111.98(15)
C17 C12 C13 118.78(16)
C17 C12 C11 122.63(15)
C13 C12 C11 118.56(16)
C14 C13 C12 120.63(19)
C14 C13 H13 119.7
C12 C13 H13 119.7
C15 C14 C13 121.29(18)
C15 C14 H14 119.4
C13 C14 H14 119.4
C14 C15 C16 117.86(16)
C14 C15 C18 121.61(18)
C16 C15 C18 120.52(19)
C17 C16 C15 121.44(18)
C17 C16 H16 119.3
C15 C16 H16 119.3
C12 C17 C16 119.99(16)
C12 C17 H17 120.0
C16 C17 H17 120.0
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.1958(19)
O2 C11 1.325(2)
O2 C8 1.4591(19)
C1 C6 1.385(2)
C1 C2 1.389(2)
C1 C10 1.500(3)
C2 C3 1.357(3)
C2 H2 0.9300
C3 C4 1.371(3)
C3 H3 0.9300
C4 C5 1.381(2)
C4 H4 0.9300
C5 C6 1.389(2)
C5 H5 0.9300
C6 C7 1.514(2)
C7 C8 1.497(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.490(3)
C8 H8 0.9800
C9 C10 1.515(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.487(2)
C12 C17 1.377(2)
C12 C13 1.379(2)
C13 C14 1.374(2)
C13 H13 0.9300
C14 C15 1.371(3)
C14 H14 0.9300
C15 C16 1.381(2)
C15 C18 1.507(2)
C16 C17 1.380(2)
C16 H16 0.9300
C17 H17 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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(3)
C10 C1 C2 C3 -177.76(18)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 -0.1(3)
C2 C1 C6 C5 -1.6(3)
C10 C1 C6 C5 177.14(17)
C2 C1 C6 C7 176.87(16)
C10 C1 C6 C7 -4.4(3)
C4 C5 C6 C1 1.2(3)
C4 C5 C6 C7 -177.31(16)
C1 C6 C7 C8 21.7(2)
C5 C6 C7 C8 -159.78(16)
C11 O2 C8 C9 113.55(18)
C11 O2 C8 C7 -126.44(17)
C6 C7 C8 O2 -168.63(13)
C6 C7 C8 C9 -50.8(2)
O2 C8 C9 C10 -178.77(15)
C7 C8 C9 C10 63.2(2)
C6 C1 C10 C9 15.5(3)
C2 C1 C10 C9 -165.73(17)
C8 C9 C10 C1 -44.1(2)
C8 O2 C11 O1 9.9(3)
C8 O2 C11 C12 -168.68(15)
O1 C11 C12 C17 177.00(17)
O2 C11 C12 C17 -4.4(2)
O1 C11 C12 C13 -5.1(3)
O2 C11 C12 C13 173.52(16)
C17 C12 C13 C14 1.1(3)
C11 C12 C13 C14 -176.93(17)
C12 C13 C14 C15 -0.9(3)
C13 C14 C15 C16 -0.2(3)
C13 C14 C15 C18 178.79(18)
C14 C15 C16 C17 1.0(3)
C18 C15 C16 C17 -178.00(17)
C13 C12 C17 C16 -0.3(3)
C11 C12 C17 C16 177.63(16)
C15 C16 C17 C12 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304743
