#------------------------------------------------------------------------------
#$Date: 2019-11-10 06:38:51 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/55/4515568.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_4515568
loop_
_publ_author_name
'Teng, Shenghan'
'Tessensohn, Malcolm E.'
'Webster, Richard D.'
'Zhou, Jianrong Steve'
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              7439
_journal_paper_doi               10.1021/acscatal.8b02029
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 107.7105(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1834(3)
_cell_length_b                   5.2643(2)
_cell_length_c                   13.7823(4)
_cell_measurement_reflns_used    167
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.8931
_cell_measurement_theta_min      4.7316
_cell_volume                     634.72(4)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13875
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.276
_refine_ls_abs_structure_details
;

Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0593
_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)+(0.0970P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                2813
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b02029_si_003.cif
_cod_data_source_block           zhou83m
_cod_database_code               4515568
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 1.1056(3) 0.5407(5) 0.39665(18) 0.0139(5) Uani d . . 1
H H1 1.0813 0.6882 0.3487 0.017 Uiso calc U R 1
C C2 1.2713(3) 0.5630(6) 0.46386(19) 0.0171(5) Uani d . . 1
H H2A 1.2953 0.4219 0.5137 0.021 Uiso calc U R 1
H H2B 1.2854 0.7249 0.5022 0.021 Uiso calc U R 1
C C3 1.3802(3) 0.5543(6) 0.39943(19) 0.0176(5) Uani d . . 1
H H3A 1.4871 0.5623 0.4445 0.021 Uiso calc U R 1
H H3B 1.3619 0.7035 0.3536 0.021 Uiso calc U R 1
C C4 1.3572(3) 0.3110(5) 0.33603(19) 0.0166(5) Uani d . . 1
H H4A 1.3874 0.1626 0.3819 0.02 Uiso calc U R 1
H H4B 1.4235 0.3152 0.2913 0.02 Uiso calc U R 1
C C5 1.1904(3) 0.2823(6) 0.27090(19) 0.0159(5) Uani d . . 1
H H5A 1.1777 0.1178 0.2345 0.019 Uiso calc U R 1
H H5B 1.1648 0.4192 0.2192 0.019 Uiso calc U R 1
C C6 1.0789(3) 0.2940(5) 0.33448(18) 0.0135(5) Uani d . . 1
H H6 1.1001 0.1469 0.3827 0.016 Uiso calc U R 1
C C7 0.9161(3) 0.2768(6) 0.26709(18) 0.0158(5) Uani d . . 1
H H7 0.8797 0.4079 0.2184 0.019 Uiso calc U R 1
C C8 0.8191(3) 0.0920(5) 0.27049(19) 0.0154(5) Uani d . . 1
H H8 0.8561 -0.0369 0.3201 0.018 Uiso calc U R 1
C C9 0.6593(3) 0.0673(5) 0.20466(18) 0.0146(5) Uani d . . 1
C C10 0.5909(3) 0.2452(5) 0.12851(18) 0.0144(5) Uani d . . 1
H H10 0.6483 0.3874 0.1184 0.017 Uiso calc U R 1
C C11 0.4412(3) 0.2161(5) 0.0681(2) 0.0157(5) Uani d . . 1
H H11 0.3968 0.3378 0.0167 0.019 Uiso calc U R 1
C C12 0.3555(3) 0.0107(5) 0.08200(18) 0.0150(5) Uani d . . 1
C C13 0.4195(3) -0.1679(5) 0.15715(19) 0.0154(5) Uani d . . 1
H H13 0.3609 -0.3086 0.1673 0.019 Uiso calc U R 1
C C14 0.5713(3) -0.1375(5) 0.21762(19) 0.0156(5) Uani d . . 1
H H14 0.6154 -0.2598 0.2688 0.019 Uiso calc U R 1
C C15 0.1227(3) -0.2228(6) 0.0206(2) 0.0213(6) Uani d . . 1
H H15A 0.1799 -0.3725 0.0107 0.032 Uiso calc U R 1
H H15B 0.0244 -0.2157 -0.0333 0.032 Uiso calc U R 1
H H15C 0.1046 -0.2338 0.087 0.032 Uiso calc U R 1
O O1 1.0026(2) 0.5426(4) 0.45664(13) 0.0178(4) Uani d . . 1
H H1A 0.9988 0.6896 0.4795 0.027 Uiso calc U R 1
O O2 0.20819(19) -0.0002(4) 0.01708(14) 0.0178(4) Uani d . . 1
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
O1 C1 C2 111.12(18)
O1 C1 C6 107.9(2)
C2 C1 C6 111.4(2)
C1 C2 C3 110.68(18)
C2 C3 C4 110.9(2)
C3 C4 C5 111.0(2)
C4 C5 C6 112.52(19)
C7 C6 C1 110.8(2)
C7 C6 C5 110.80(19)
C1 C6 C5 109.3(2)
C8 C7 C6 125.0(2)
C7 C8 C9 126.4(2)
C14 C9 C10 117.9(2)
C14 C9 C8 119.8(2)
C10 C9 C8 122.4(2)
C11 C10 C9 120.9(2)
C10 C11 C12 120.4(2)
O2 C12 C11 115.4(2)
O2 C12 C13 124.4(2)
C11 C12 C13 120.2(2)
C12 C13 C14 119.0(2)
C9 C14 C13 121.7(2)
C12 O2 C15 117.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.433(3)
C1 C2 1.526(3)
C1 C6 1.534(4)
C2 C3 1.527(3)
C3 C4 1.528(4)
C4 C5 1.529(3)
C5 C6 1.538(3)
C6 C7 1.504(3)
C7 C8 1.329(4)
C8 C9 1.477(3)
C9 C14 1.391(4)
C9 C10 1.404(3)
C10 C11 1.382(3)
C11 C12 1.384(4)
C12 O2 1.378(3)
C12 C13 1.390(4)
C13 C14 1.399(3)
C15 O2 1.420(3)
