#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134963.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_4134963
loop_
_publ_author_name
'Wang, Huanan'
'Luo, Hongwen'
'Zhang, Zhan-Ming'
'Zheng, Wei-Feng'
'Yin, Yu'
'Qian, Hui'
'Zhang, Junliang'
'Ma, Shengming'
_publ_section_title
;
 Pd-Catalyzed Enantioselective Syntheses of Trisubstituted Allenes via
 Coupling of Propargylic Benzoates with Organoboronic Acids.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9763
_journal_page_last               9771
_journal_paper_doi               10.1021/jacs.0c02876
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H24 O3'
_chemical_formula_sum            'C25 H24 O3'
_chemical_formula_weight         372.44
_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
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 96.1030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9325(2)
_cell_length_b                   10.8470(3)
_cell_length_c                   10.2984(3)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    152.(2)
_cell_measurement_theta_max      70.3250
_cell_measurement_theta_min      4.3176
_cell_volume                     992.17(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      152.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26665
_diffrn_reflns_theta_full        70.48
_diffrn_reflns_theta_max         70.48
_diffrn_reflns_theta_min         4.32
_diffrn_source                   'Sealed x-ray tube'
_diffrn_source_type              'Bruker IuS 3.0'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details
;

Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0321
_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)+(0.0448P)²+0.2264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                3700
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02876_si_002.cif
_cod_data_source_block           WHN_3_021
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4134963.cif.
;
_cod_database_code               4134963
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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1398(2) 0.63470(16) -0.09748(17) 0.0391(4) Uani d . . . 1 . .
C C1 0.3749(3) 0.7464(2) 0.0982(3) 0.0353(5) Uani d . . . 1 . .
H H1 0.432466 0.675293 0.082503 0.042 Uiso calc U . R 1 . .
O O2 0.18852(19) 0.43458(15) -0.06319(15) 0.0320(4) Uani d . . . 1 . .
C C2 0.4160(3) 0.8600(2) 0.0512(3) 0.0376(6) Uani d . . . 1 . .
H H2 0.501084 0.866226 0.003546 0.045 Uiso calc U . R 1 . .
C C3 0.3332(3) 0.9644(2) 0.0735(2) 0.0349(5) Uani d . . . 1 . .
H H3 0.360532 1.042142 0.040665 0.042 Uiso calc U . R 1 . .
O O3 0.1987(2) 0.24171(16) 0.01322(17) 0.0378(4) Uani d . . . 1 . .
C C4 0.2100(3) 0.9544(2) 0.1442(2) 0.0335(5) Uani d . . . 1 . .
H H4 0.153569 1.025874 0.160839 0.04 Uiso calc U . R 1 . .
C C5 0.1688(3) 0.8407(2) 0.1907(2) 0.0302(5) Uani d . . . 1 . .
H H5 0.083903 0.834805 0.238665 0.036 Uiso calc U . R 1 . .
C C6 0.2505(2) 0.7351(2) 0.1680(2) 0.0286(5) Uani d . . . 1 . .
C C7 0.2010(3) 0.6105(2) 0.2149(2) 0.0288(5) Uani d . . . 1 . .
H H7 0.142588 0.627459 0.290604 0.035 Uiso calc U . R 1 . .
C C9 0.3096(3) 0.4107(2) 0.2999(2) 0.0274(5) Uani d . . . 1 . .
C C8 0.3297(3) 0.5276(2) 0.2660(2) 0.0293(5) Uani d . . . 1 . .
H H8 0.428989 0.56015 0.274351 0.035 Uiso calc U . R 1 . .
C C10 0.1567(2) 0.3576(2) 0.2679(2) 0.0257(4) Uani d . . . 1 . .
C C11 0.0820(2) 0.4023(2) 0.1364(2) 0.0271(5) Uani d . . . 1 . .
H H11 -0.025848 0.375967 0.126312 0.032 Uiso calc U . R 1 . .
C C12 0.0905(2) 0.5422(2) 0.1106(2) 0.0272(4) Uani d . . . 1 . .
H H12 -0.012375 0.578711 0.109889 0.033 Uiso calc U . R 1 . .
C C13 0.1395(2) 0.5493(2) -0.0251(2) 0.0293(5) Uani d . . . 1 . .
C C14 0.1610(3) 0.3458(2) 0.0276(2) 0.0286(5) Uani d . . . 1 . .
C C15 0.0857(2) 0.2729(2) 0.3334(2) 0.0287(5) Uani d . . . 1 . .
H H15 -0.008252 0.244986 0.291756 0.034 Uiso calc U . R 1 . .
C C16 0.1340(3) 0.2174(2) 0.4611(2) 0.0295(5) Uani d . . . 1 . .
C C17 0.1911(3) 0.2871(3) 0.5682(2) 0.0369(5) Uani d . . . 1 . .
H H17 0.198105 0.374108 0.560142 0.044 Uiso calc U . R 1 . .
C C18 0.2383(3) 0.2314(3) 0.6872(3) 0.0452(7) Uani d . . . 1 . .
H H18 0.27841 0.280117 0.759308 0.054 Uiso calc U . R 1 . .
C C19 0.2268(3) 0.1054(3) 0.7002(3) 0.0464(7) Uani d . . . 1 . .
H H19 0.260215 0.067123 0.781115 0.056 Uiso calc U . R 1 . .
C C20 0.1669(3) 0.0349(3) 0.5961(3) 0.0437(6) Uani d . . . 1 . .
H H20 0.158113 -0.051879 0.605608 0.052 Uiso calc U . R 1 . .
C C21 0.1192(3) 0.0905(2) 0.4774(3) 0.0355(5) Uani d . . . 1 . .
H H21 0.076107 0.041568 0.406509 0.043 Uiso calc U . R 1 . .
C C22 0.4381(3) 0.3322(2) 0.3616(2) 0.0308(5) Uani d . . . 1 . .
H H22A 0.420865 0.315036 0.453267 0.037 Uiso calc U . R 1 . .
H H22B 0.53258 0.380104 0.363208 0.037 Uiso calc U . R 1 . .
C C23 0.4591(3) 0.2101(2) 0.2931(3) 0.0378(6) Uani d . . . 1 . .
H H23A 0.508593 0.225984 0.21321 0.045 Uiso calc U . R 1 . .
H H23B 0.358792 0.174147 0.265866 0.045 Uiso calc U . R 1 . .
C C24 0.5526(3) 0.1162(3) 0.3772(3) 0.0452(6) Uani d . . . 1 . .
H H24A 0.500733 0.09695 0.455097 0.054 Uiso calc U . R 1 . .
H H24B 0.559057 0.039031 0.326781 0.054 Uiso calc U . R 1 . .
C C25 0.7092(3) 0.1609(3) 0.4210(3) 0.0504(7) Uani d . . . 1 . .
H H25A 0.758343 0.186642 0.344805 0.076 Uiso calc U . R 1 . .
H H25B 0.767277 0.094078 0.46639 0.076 Uiso calc U . R 1 . .
H H25C 0.704061 0.230941 0.480438 0.076 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.9(2) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C14 O2 C13 . . 110.41(17) ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 119.4(2) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.3(2) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.5(2) ?
C5 C6 C7 . . 120.24(19) ?
C1 C6 C7 . . 121.2(2) ?
C8 C7 C6 . . 113.87(19) ?
C8 C7 C12 . . 110.99(19) ?
C6 C7 C12 . . 112.80(18) ?
C8 C7 H7 . . 106.2 ?
C6 C7 H7 . . 106.2 ?
C12 C7 H7 . . 106.2 ?
C8 C9 C10 . . 117.2(2) ?
C8 C9 C22 . . 121.9(2) ?
C10 C9 C22 . . 120.8(2) ?
C9 C8 C7 . . 122.7(2) ?
C9 C8 H8 . . 118.7 ?
C7 C8 H8 . . 118.7 ?
C15 C10 C9 . . 128.9(2) ?
C15 C10 C11 . . 118.66(19) ?
C9 C10 C11 . . 112.24(18) ?
C14 C11 C10 . . 109.51(18) ?
C14 C11 C12 . . 103.63(18) ?
C10 C11 C12 . . 116.15(19) ?
C14 C11 H11 . . 109.1 ?
C10 C11 H11 . . 109.1 ?
C12 C11 H11 . . 109.1 ?
C13 C12 C11 . . 103.49(18) ?
C13 C12 C7 . . 112.76(18) ?
C11 C12 C7 . . 112.74(18) ?
C13 C12 H12 . . 109.2 ?
C11 C12 H12 . . 109.2 ?
C7 C12 H12 . . 109.2 ?
O1 C13 O2 . . 119.9(2) ?
O1 C13 C12 . . 129.8(2) ?
O2 C13 C12 . . 110.31(18) ?
O3 C14 O2 . . 120.2(2) ?
O3 C14 C11 . . 129.4(2) ?
O2 C14 C11 . . 110.38(19) ?
C10 C15 C16 . . 128.5(2) ?
C10 C15 H15 . . 115.8 ?
C16 C15 H15 . . 115.8 ?
C17 C16 C21 . . 118.2(2) ?
C17 C16 C15 . . 122.5(2) ?
C21 C16 C15 . . 119.3(2) ?
C16 C17 C18 . . 121.0(3) ?
C16 C17 H17 . . 119.5 ?
C18 C17 H17 . . 119.5 ?
C19 C18 C17 . . 119.9(3) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C20 C19 C18 . . 120.1(3) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C21 . . 120.1(3) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
C20 C21 C16 . . 120.7(3) ?
C20 C21 H21 . . 119.7 ?
C16 C21 H21 . . 119.7 ?
C9 C22 C23 . . 114.86(19) ?
C9 C22 H22A . . 108.6 ?
C23 C22 H22A . . 108.6 ?
C9 C22 H22B . . 108.6 ?
C23 C22 H22B . . 108.6 ?
H22A C22 H22B . . 107.5 ?
C22 C23 C24 . . 113.9(2) ?
C22 C23 H23A . . 108.8 ?
C24 C23 H23A . . 108.8 ?
C22 C23 H23B . . 108.8 ?
C24 C23 H23B . . 108.8 ?
H23A C23 H23B . . 107.7 ?
C25 C24 C23 . . 113.0(3) ?
C25 C24 H24A . . 109.0 ?
C23 C24 H24A . . 109.0 ?
C25 C24 H24B . . 109.0 ?
C23 C24 H24B . . 109.0 ?
H24A C24 H24B . . 107.8 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.190(3) ?
C1 C2 . 1.388(4) ?
C1 C6 . 1.391(3) ?
C1 H1 . 0.95 ?
O2 C14 . 1.383(3) ?
O2 C13 . 1.389(3) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.386(4) ?
C3 H3 . 0.95 ?
O3 C14 . 1.192(3) ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.517(3) ?
C7 C8 . 1.509(3) ?
C7 C12 . 1.566(3) ?
C7 H7 . 1.0 ?
C9 C8 . 1.333(3) ?
C9 C10 . 1.486(3) ?
C9 C22 . 1.514(3) ?
C8 H8 . 0.95 ?
C10 C15 . 1.339(3) ?
C10 C11 . 1.524(3) ?
C11 C14 . 1.515(3) ?
C11 C12 . 1.543(3) ?
C11 H11 . 1.0 ?
C12 C13 . 1.510(3) ?
C12 H12 . 1.0 ?
C15 C16 . 1.469(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.389(3) ?
C16 C21 . 1.395(3) ?
C17 C18 . 1.390(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.378(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.378(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.390(4) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 C23 . 1.521(3) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.527(4) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.504(4) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336440
