#------------------------------------------------------------------------------
#$Date: 2022-01-03 22:53:40 +0200 (Mon, 03 Jan 2022) $
#$Revision: 271728 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/92/4519232.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_4519232
loop_
_publ_author_name
'Tanpure, Sudhakar Dattatray'
'Kuo, Tung-Chun'
'Cheng, Mu-Jeng'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of
 Bicyclo[3.2.1]oct-6-ene Frameworks via (4 + 3)-Cycloadditions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              536
_journal_page_last               543
_journal_paper_doi               10.1021/acscatal.1c04483
_journal_year                    2021
_chemical_formula_sum            'C35 H30 O'
_chemical_formula_weight         466.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.199(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2675(6)
_cell_length_b                   22.1370(16)
_cell_length_c                   13.9373(10)
_cell_measurement_reflns_used    7499
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1865
_cell_measurement_theta_min      2.3522
_cell_volume                     2543.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35475
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         1.730
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0603
_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
'w=1/[σ²(Fo²)+(0.0458P)²+0.9141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3990
_reflns_number_total             5221
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c04483_si_003.cif
_cod_data_source_block           mo_210455LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519232
_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           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15966(11) 0.11813(4) 0.52677(6) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.60050(19) 0.21062(8) 0.89897(11) 0.0349(4) Uani 1 1 d . . . . .
H1 H 0.6293 0.2059 0.9658 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6037(2) 0.16135(8) 0.83799(11) 0.0356(4) Uani 1 1 d . . . . .
H30 H 0.6338 0.1227 0.8631 0.043 Uiso 1 1 calc R U . . .
C3 C 0.56300(19) 0.16836(7) 0.74009(11) 0.0285(3) Uani 1 1 d . . . . .
H3 H 0.5656 0.1344 0.6985 0.034 Uiso 1 1 calc R U . . .
C4 C 0.51845(16) 0.22464(6) 0.70244(10) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.47170(16) 0.23392(6) 0.59591(9) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.4075 0.2722 0.5900 0.024 Uiso 1 1 calc R U . . .
C6 C 0.62028(17) 0.24173(6) 0.53210(10) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.67733(17) 0.17929(7) 0.49935(10) 0.0235(3) Uani 1 1 d . . . . .
H15 H 0.6810 0.1498 0.5528 0.028 Uiso 1 1 calc R U . . .
H14 H 0.7858 0.1817 0.4738 0.028 Uiso 1 1 calc R U . . .
C8 C 0.54523(17) 0.16216(6) 0.41915(9) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.59553(16) 0.11179(6) 0.35420(10) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.63198(19) 0.12220(7) 0.26165(10) 0.0273(3) Uani 1 1 d . . . . .
H16 H 0.6331 0.1626 0.2386 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6681(2) 0.07432(7) 0.19906(11) 0.0302(4) Uani 1 1 d . . . . .
C12 C 0.66752(18) 0.01421(7) 0.23338(10) 0.0265(3) Uani 1 1 d . . . . .
C13 C 0.6932(2) -0.03360(7) 0.16870(11) 0.0365(4) Uani 1 1 d . . . . .
H17 H 0.6923 -0.0742 0.1909 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7193(3) -0.02218(8) 0.07505(12) 0.0519(6) Uani 1 1 d . . . . .
H2 H 0.7336 -0.0547 0.0321 0.062 Uiso 1 1 calc R U . . .
C15 C 0.51483(17) 0.27352(7) 0.76530(10) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.4839 0.3122 0.7409 0.030 Uiso 1 1 calc R U . . .
C16 C 0.55560(18) 0.26649(8) 0.86279(10) 0.0298(4) Uani 1 1 d . . . . .
H4 H 0.5526 0.3002 0.9047 0.036 Uiso 1 1 calc R U . . .
C17 C 0.36269(16) 0.18385(6) 0.55466(9) 0.0183(3) Uani 1 1 d . . . . .
C18 C 0.39329(16) 0.14885(6) 0.47077(9) 0.0178(3) Uani 1 1 d . . . . .
C19 C 0.75417(18) 0.28010(7) 0.58256(11) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.8406 0.2866 0.5391 0.046 Uiso 1 1 calc R U . . .
H9 H 0.7986 0.2592 0.6406 0.046 Uiso 1 1 calc R U . . .
H8 H 0.7094 0.3192 0.6003 0.046 Uiso 1 1 calc R U . . .
C20 C 0.55415(17) 0.26802(6) 0.43584(10) 0.0232(3) Uani 1 1 d . . . . .
C21 C 0.51521(17) 0.22412(6) 0.37356(10) 0.0214(3) Uani 1 1 d . . . . .
H10 H 0.4740 0.2305 0.3089 0.026 Uiso 1 1 calc R U . . .
C22 C 0.5286(2) 0.33445(7) 0.42137(11) 0.0318(4) Uani 1 1 d . . . . .
H12 H 0.4648 0.3414 0.3603 0.048 Uiso 1 1 calc R U . . .
H11 H 0.6340 0.3546 0.4199 0.048 Uiso 1 1 calc R U . . .
H13 H 0.4705 0.3508 0.4744 0.048 Uiso 1 1 calc R U . . .
C23 C 0.60437(17) 0.05163(7) 0.38931(10) 0.0249(3) Uani 1 1 d . . . . .
H21 H 0.5857 0.0440 0.4547 0.030 Uiso 1 1 calc R U . . .
C24 C 0.63899(18) 0.00462(7) 0.33127(10) 0.0273(3) Uani 1 1 d . . . . .
H20 H 0.6441 -0.0352 0.3567 0.033 Uiso 1 1 calc R U . . .
C25 C 0.7003(3) 0.08446(8) 0.10215(12) 0.0526(6) Uani 1 1 d . . . . .
H19 H 0.7048 0.1247 0.0787 0.063 Uiso 1 1 calc R U . . .
C26 C 0.7250(3) 0.03745(9) 0.04189(13) 0.0644(7) Uani 1 1 d . . . . .
H18 H 0.7463 0.0452 -0.0230 0.077 Uiso 1 1 calc R U . . .
C27 C 0.26630(16) 0.11040(6) 0.45496(9) 0.0183(3) Uani 1 1 d . . . . .
C28 C 0.22175(16) 0.16371(6) 0.58582(9) 0.0188(3) Uani 1 1 d . . . . .
C29 C 0.12719(18) 0.17983(7) 0.66876(10) 0.0251(3) Uani 1 1 d . . . . .
H23 H 0.1336 0.1467 0.7156 0.038 Uiso 1 1 calc R U . . .
H24 H 0.0136 0.1867 0.6462 0.038 Uiso 1 1 calc R U . . .
H22 H 0.1720 0.2167 0.6992 0.038 Uiso 1 1 calc R U . . .
C30 C 0.21447(16) 0.06652(6) 0.38020(10) 0.0202(3) Uani 1 1 d . . . . .
C31 C 0.14873(18) 0.01116(7) 0.40454(11) 0.0260(3) Uani 1 1 d . . . . .
H29 H 0.1356 0.0019 0.4701 0.031 Uiso 1 1 calc R U . . .
C32 C 0.1025(2) -0.03031(7) 0.33380(12) 0.0369(4) Uani 1 1 d . . . . .
H28 H 0.0581 -0.0681 0.3509 0.044 Uiso 1 1 calc R U . . .
C33 C 0.1206(2) -0.01713(8) 0.23788(13) 0.0396(4) Uani 1 1 d . . . . .
H27 H 0.0894 -0.0459 0.1894 0.048 Uiso 1 1 calc R U . . .
C34 C 0.1841(2) 0.03782(7) 0.21315(11) 0.0325(4) Uani 1 1 d . . . . .
H26 H 0.1960 0.0469 0.1474 0.039 Uiso 1 1 calc R U . . .
C35 C 0.23033(17) 0.07966(7) 0.28330(10) 0.0240(3) Uani 1 1 d . . . . .
H25 H 0.2731 0.1176 0.2656 0.029 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 O1 C27 106.96(10) . . ?
C16 C1 C2 119.99(14) . . ?
C16 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.04(16) . . ?
C1 C2 H30 120.0 . . ?
C3 C2 H30 120.0 . . ?
C2 C3 C4 120.58(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C15 118.39(13) . . ?
C3 C4 C5 122.06(12) . . ?
C15 C4 C5 119.55(13) . . ?
C17 C5 C4 111.91(11) . . ?
C17 C5 C6 109.41(10) . . ?
C4 C5 C6 114.36(11) . . ?
C17 C5 H6 106.9 . . ?
C4 C5 H6 106.9 . . ?
C6 C5 H6 106.9 . . ?
C19 C6 C20 113.21(12) . . ?
C19 C6 C7 114.12(12) . . ?
C20 C6 C7 100.33(11) . . ?
C19 C6 C5 111.70(11) . . ?
C20 C6 C5 107.08(11) . . ?
C7 C6 C5 109.66(11) . . ?
C6 C7 C8 102.60(11) . . ?
C6 C7 H15 111.2 . . ?
C8 C7 H15 111.2 . . ?
C6 C7 H14 111.2 . . ?
C8 C7 H14 111.2 . . ?
H15 C7 H14 109.2 . . ?
C9 C8 C18 114.38(11) . . ?
C9 C8 C21 117.20(11) . . ?
C18 C8 C21 104.86(11) . . ?
C9 C8 C7 113.66(11) . . ?
C18 C8 C7 105.58(10) . . ?
C21 C8 C7 99.49(11) . . ?
C10 C9 C23 118.35(13) . . ?
C10 C9 C8 122.00(13) . . ?
C23 C9 C8 119.65(12) . . ?
C9 C10 C11 121.73(14) . . ?
C9 C10 H16 119.1 . . ?
C11 C10 H16 119.1 . . ?
C25 C11 C12 118.58(14) . . ?
C25 C11 C10 122.13(14) . . ?
C12 C11 C10 119.27(13) . . ?
C11 C12 C13 118.90(13) . . ?
C11 C12 C24 118.13(13) . . ?
C13 C12 C24 122.96(14) . . ?
C14 C13 C12 120.86(15) . . ?
C14 C13 H17 119.6 . . ?
C12 C13 H17 119.6 . . ?
C13 C14 C26 120.19(16) . . ?
C13 C14 H2 119.9 . . ?
C26 C14 H2 119.9 . . ?
C16 C15 C4 120.97(14) . . ?
C16 C15 H5 119.5 . . ?
C4 C15 H5 119.5 . . ?
C1 C16 C15 120.02(14) . . ?
C1 C16 H4 120.0 . . ?
C15 C16 H4 120.0 . . ?
C28 C17 C18 106.91(12) . . ?
C28 C17 C5 128.57(12) . . ?
C18 C17 C5 124.51(12) . . ?
C27 C18 C17 106.83(12) . . ?
C27 C18 C8 134.45(12) . . ?
C17 C18 C8 118.68(11) . . ?
C6 C19 H7 109.5 . . ?
C6 C19 H9 109.5 . . ?
H7 C19 H9 109.5 . . ?
C6 C19 H8 109.5 . . ?
H7 C19 H8 109.5 . . ?
H9 C19 H8 109.5 . . ?
C21 C20 C22 127.32(14) . . ?
C21 C20 C6 110.48(12) . . ?
C22 C20 C6 122.05(13) . . ?
C20 C21 C8 111.23(12) . . ?
C20 C21 H10 124.4 . . ?
C8 C21 H10 124.4 . . ?
C20 C22 H12 109.5 . . ?
C20 C22 H11 109.5 . . ?
H12 C22 H11 109.5 . . ?
C20 C22 H13 109.5 . . ?
H12 C22 H13 109.5 . . ?
H11 C22 H13 109.5 . . ?
C24 C23 C9 121.35(13) . . ?
C24 C23 H21 119.3 . . ?
C9 C23 H21 119.3 . . ?
C23 C24 C12 120.96(14) . . ?
C23 C24 H20 119.5 . . ?
C12 C24 H20 119.5 . . ?
C26 C25 C11 121.00(16) . . ?
C26 C25 H19 119.5 . . ?
C11 C25 H19 119.5 . . ?
C25 C26 C14 120.42(16) . . ?
C25 C26 H18 119.8 . . ?
C14 C26 H18 119.8 . . ?
C18 C27 O1 109.23(11) . . ?
C18 C27 C30 135.55(12) . . ?
O1 C27 C30 115.15(11) . . ?
C17 C28 O1 110.04(11) . . ?
C17 C28 C29 133.43(13) . . ?
O1 C28 C29 116.52(11) . . ?
C28 C29 H23 109.5 . . ?
C28 C29 H24 109.5 . . ?
H23 C29 H24 109.5 . . ?
C28 C29 H22 109.5 . . ?
H23 C29 H22 109.5 . . ?
H24 C29 H22 109.5 . . ?
C31 C30 C35 118.99(13) . . ?
C31 C30 C27 120.61(12) . . ?
C35 C30 C27 120.40(12) . . ?
C32 C31 C30 120.25(14) . . ?
C32 C31 H29 119.9 . . ?
C30 C31 H29 119.9 . . ?
C31 C32 C33 120.30(15) . . ?
C31 C32 H28 119.9 . . ?
C33 C32 H28 119.9 . . ?
C34 C33 C32 119.78(15) . . ?
C34 C33 H27 120.1 . . ?
C32 C33 H27 120.1 . . ?
C33 C34 C35 120.38(15) . . ?
C33 C34 H26 119.8 . . ?
C35 C34 H26 119.8 . . ?
C34 C35 C30 120.28(14) . . ?
C34 C35 H25 119.9 . . ?
C30 C35 H25 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C28 1.3775(16) . ?
O1 C27 1.3920(15) . ?
C1 C16 1.376(2) . ?
C1 C2 1.384(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(2) . ?
C2 H30 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C15 1.394(2) . ?
C4 C5 1.5205(18) . ?
C5 C17 1.5151(19) . ?
C5 C6 1.5779(18) . ?
C5 H6 1.0000 . ?
C6 C19 1.5256(19) . ?
C6 C20 1.526(2) . ?
C6 C7 1.540(2) . ?
C7 C8 1.5515(19) . ?
C7 H15 0.9900 . ?
C7 H14 0.9900 . ?
C8 C9 1.5136(19) . ?
C8 C18 1.5214(18) . ?
C8 C21 1.5242(19) . ?
C9 C10 1.3656(19) . ?
C9 C23 1.419(2) . ?
C10 C11 1.418(2) . ?
C10 H16 0.9500 . ?
C11 C25 1.413(2) . ?
C11 C12 1.414(2) . ?
C12 C13 1.416(2) . ?
C12 C24 1.417(2) . ?
C13 C14 1.362(2) . ?
C13 H17 0.9500 . ?
C14 C26 1.400(3) . ?
C14 H2 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H5 0.9500 . ?
C16 H4 0.9500 . ?
C17 C28 1.3488(19) . ?
C17 C18 1.4403(18) . ?
C18 C27 1.3570(19) . ?
C19 H7 0.9800 . ?
C19 H9 0.9800 . ?
C19 H8 0.9800 . ?
C20 C21 1.327(2) . ?
C20 C22 1.497(2) . ?
C21 H10 0.9500 . ?
C22 H12 0.9800 . ?
C22 H11 0.9800 . ?
C22 H13 0.9800 . ?
C23 C24 1.361(2) . ?
C23 H21 0.9500 . ?
C24 H20 0.9500 . ?
C25 C26 1.362(2) . ?
C25 H19 0.9500 . ?
C26 H18 0.9500 . ?
C27 C30 1.4655(19) . ?
C28 C29 1.4855(18) . ?
C29 H23 0.9800 . ?
C29 H24 0.9800 . ?
C29 H22 0.9800 . ?
C30 C31 1.3926(19) . ?
C30 C35 1.3970(19) . ?
C31 C32 1.381(2) . ?
C31 H29 0.9500 . ?
C32 C33 1.387(2) . ?
C32 H28 0.9500 . ?
C33 C34 1.378(2) . ?
C33 H27 0.9500 . ?
C34 C35 1.380(2) . ?
C34 H26 0.9500 . ?
C35 H25 0.9500 . ?
