#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033381.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_4033381
loop_
_publ_author_name
'Zhao, Jidong'
'Yang, Shuang'
'Xie, Xin'
'Li, Xiangdong'
'Liu, Yuanhong'
_publ_section_title
;
 Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio-
 and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through
 Cyclodimerization of 1-Ethynyl-2-propenyl Esters.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1287
_journal_page_last               1297
_journal_paper_doi               10.1021/acs.joc.7b02816
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C26 H22 Br2 O4'
_chemical_formula_weight         558.25
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.600(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8138(14)
_cell_length_b                   10.2034(10)
_cell_length_c                   17.2024(18)
_cell_measurement_reflns_used    4138
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      45.948
_cell_measurement_theta_min      4.642
_cell_volume                     2423.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.865
_exptl_absorpt_coefficient_mu    3.374
_exptl_absorpt_correction_T_max  0.7345
_exptl_absorpt_correction_T_min  0.4166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0342P)²+2.2855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3105
_reflns_number_total             4772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b02816_si_004.cif
_cod_data_source_block           mo_dm17392_0m
_cod_depositor_comments
'Adding full bibliography for 4033380--4033384.cif.'
_cod_database_code               4033381
_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. 
;
_shelx_estimated_absorpt_t_min   0.552
_shelx_estimated_absorpt_t_max   0.688
_shelxl_version_number           2013-4
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
Br1 Br -0.21435(4) -0.18928(7) 0.47382(4) 0.1237(3) Uani 1 1 d . .
Br2 Br 0.84621(3) 0.39118(4) 0.44264(3) 0.07137(17) Uani 1 1 d . .
O1 O 0.55514(17) -0.2008(2) 0.30570(13) 0.0545(6) Uani 1 1 d . .
O2 O 0.5359(2) -0.2616(3) 0.42996(16) 0.0719(8) Uani 1 1 d . .
O3 O 0.26314(17) -0.0494(2) 0.15665(13) 0.0532(6) Uani 1 1 d . .
O4 O 0.2094(2) 0.1532(3) 0.12922(15) 0.0682(8) Uani 1 1 d . .
C1 C 0.5039(2) -0.0845(3) 0.31160(18) 0.0437(8) Uani 1 1 d . .
C2 C 0.4423(2) -0.0410(3) 0.36243(18) 0.0439(8) Uani 1 1 d . .
H2 H 0.4260 -0.0820 0.4085 0.053 Uiso 1 1 calc R U
C3 C 0.4025(2) 0.0885(3) 0.33211(18) 0.0413(7) Uani 1 1 d . .
H3 H 0.3899 0.1493 0.3747 0.050 Uiso 1 1 calc R U
C4 C 0.4860(2) 0.1374(3) 0.28212(18) 0.0415(7) Uani 1 1 d . .
H4 H 0.4608 0.1994 0.2430 0.050 Uiso 1 1 calc R U
C5 C 0.5108(2) 0.0058(3) 0.24239(17) 0.0434(8) Uani 1 1 d . .
H5 H 0.5746 0.0053 0.2190 0.052 Uiso 1 1 calc R U
C6 C 0.4292(2) -0.0297(3) 0.18595(18) 0.0472(8) Uani 1 1 d . .
H6 H 0.4419 -0.0714 0.1393 0.057 Uiso 1 1 calc R U
C7 C 0.3400(2) -0.0002(3) 0.20418(18) 0.0452(8) Uani 1 1 d . .
C8 C 0.3113(2) 0.0704(3) 0.27806(19) 0.0452(8) Uani 1 1 d . .
H8 H 0.2877 0.1577 0.2632 0.054 Uiso 1 1 calc R U
C9 C 0.2302(2) -0.0003(3) 0.31641(19) 0.0484(8) Uani 1 1 d . .
H9 H 0.2414 -0.0854 0.3339 0.058 Uiso 1 1 calc R U
C10 C 0.1440(2) 0.0516(4) 0.3268(2) 0.0523(9) Uani 1 1 d . .
H10 H 0.1352 0.1369 0.3088 0.063 Uiso 1 1 calc R U
C11 C 0.0606(2) -0.0087(4) 0.3630(2) 0.0508(9) Uani 1 1 d . .
C12 C 0.0621(3) -0.1344(4) 0.3941(2) 0.0659(11) Uani 1 1 d . .
H12 H 0.1188 -0.1834 0.3928 0.079 Uiso 1 1 calc R U
C13 C -0.0189(3) -0.1879(5) 0.4268(2) 0.0746(12) Uani 1 1 d . .
H13 H -0.0167 -0.2722 0.4473 0.090 Uiso 1 1 calc R U
C14 C -0.1022(3) -0.1164(5) 0.4289(2) 0.0682(12) Uani 1 1 d . .
C15 C -0.1070(3) 0.0072(5) 0.3992(3) 0.0831(14) Uani 1 1 d . .
H15 H -0.1639 0.0555 0.4010 0.100 Uiso 1 1 calc R U
C16 C -0.0257(3) 0.0592(4) 0.3665(3) 0.0716(12) Uani 1 1 d . .
H16 H -0.0291 0.1433 0.3458 0.086 Uiso 1 1 calc R U
C17 C 0.2004(3) 0.0375(4) 0.12406(19) 0.0516(9) Uani 1 1 d . .
C18 C 0.1215(3) -0.0337(4) 0.0809(3) 0.0745(12) Uani 1 1 d . .
H18A H 0.0807 0.0283 0.0536 0.112 Uiso 1 1 calc R U
H18B H 0.0837 -0.0824 0.1169 0.112 Uiso 1 1 calc R U
H18C H 0.1492 -0.0928 0.0442 0.112 Uiso 1 1 calc R U
C19 C 0.5658(2) -0.2836(3) 0.3678(2) 0.0534(9) Uani 1 1 d . .
C20 C 0.6206(3) -0.4025(4) 0.3438(3) 0.0821(13) Uani 1 1 d . .
H20A H 0.6304 -0.4592 0.3878 0.123 Uiso 1 1 calc R U
H20B H 0.6823 -0.3766 0.3245 0.123 Uiso 1 1 calc R U
H20C H 0.5845 -0.4480 0.3037 0.123 Uiso 1 1 calc R U
C21 C 0.5730(2) 0.1964(3) 0.32427(18) 0.0418(7) Uani 1 1 d . .
C22 C 0.6468(3) 0.2493(3) 0.2804(2) 0.0524(9) Uani 1 1 d . .
H22 H 0.6408 0.2473 0.2264 0.063 Uiso 1 1 calc R U
C23 C 0.7284(3) 0.3043(4) 0.3147(2) 0.0557(9) Uani 1 1 d . .
H23 H 0.7768 0.3390 0.2843 0.067 Uiso 1 1 calc R U
C24 C 0.7373(2) 0.3073(3) 0.3945(2) 0.0475(8) Uani 1 1 d . .
C25 C 0.6668(2) 0.2554(3) 0.4399(2) 0.0502(8) Uani 1 1 d . .
H25 H 0.6737 0.2573 0.4938 0.060 Uiso 1 1 calc R U
C26 C 0.5851(2) 0.2001(3) 0.40461(19) 0.0481(8) Uani 1 1 d . .
H26 H 0.5373 0.1649 0.4354 0.058 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'
Br Br -0.2901 2.4595 '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
C19 O1 C1 121.1(3)
C17 O3 C7 118.0(3)
C2 C1 O1 132.8(3)
C2 C1 C5 112.0(3)
O1 C1 C5 114.9(3)
C1 C2 C3 107.5(3)
C1 C2 H2 126.3
C3 C2 H2 126.3
C2 C3 C4 101.8(2)
C2 C3 C8 112.4(3)
C4 C3 C8 108.1(2)
C2 C3 H3 111.4
C4 C3 H3 111.4
C8 C3 H3 111.4
C21 C4 C3 117.3(3)
C21 C4 C5 112.0(3)
C3 C4 C5 98.2(2)
C21 C4 H4 109.6
C3 C4 H4 109.6
C5 C4 H4 109.6
C6 C5 C1 107.4(3)
C6 C5 C4 108.7(3)
C1 C5 C4 99.3(2)
C6 C5 H5 113.5
C1 C5 H5 113.5
C4 C5 H5 113.5
C7 C6 C5 118.6(3)
C7 C6 H6 120.7
C5 C6 H6 120.7
C6 C7 O3 118.3(3)
C6 C7 C8 125.1(3)
O3 C7 C8 116.2(3)
C9 C8 C7 110.8(3)
C9 C8 C3 113.3(3)
C7 C8 C3 109.3(2)
C9 C8 H8 107.8
C7 C8 H8 107.8
C3 C8 H8 107.8
C10 C9 C8 123.6(3)
C10 C9 H9 118.2
C8 C9 H9 118.2
C9 C10 C11 127.9(3)
C9 C10 H10 116.1
C11 C10 H10 116.1
C16 C11 C12 116.7(4)
C16 C11 C10 119.9(3)
C12 C11 C10 123.3(3)
C13 C12 C11 121.3(4)
C13 C12 H12 119.4
C11 C12 H12 119.4
C14 C13 C12 119.6(4)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C15 121.2(4)
C13 C14 Br1 119.9(4)
C15 C14 Br1 118.9(3)
C14 C15 C16 118.6(4)
C14 C15 H15 120.7
C16 C15 H15 120.7
C15 C16 C11 122.6(4)
C15 C16 H16 118.7
C11 C16 H16 118.7
O4 C17 O3 123.7(3)
O4 C17 C18 126.4(4)
O3 C17 C18 109.8(3)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O2 C19 O1 123.9(3)
O2 C19 C20 126.7(4)
O1 C19 C20 109.3(3)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C26 C21 C22 117.4(3)
C26 C21 C4 124.1(3)
C22 C21 C4 118.6(3)
C23 C22 C21 121.9(3)
C23 C22 H22 119.1
C21 C22 H22 119.1
C24 C23 C22 119.1(3)
C24 C23 H23 120.5
C22 C23 H23 120.5
C25 C24 C23 121.0(3)
C25 C24 Br2 119.5(3)
C23 C24 Br2 119.5(3)
C24 C25 C26 119.4(3)
C24 C25 H25 120.3
C26 C25 H25 120.3
C21 C26 C25 121.4(3)
C21 C26 H26 119.3
C25 C26 H26 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.902(4)
Br2 C24 1.900(3)
O1 C19 1.366(4)
O1 C1 1.387(4)
O2 C19 1.179(4)
O3 C17 1.351(4)
O3 C7 1.414(4)
O4 C17 1.191(4)
C1 C2 1.314(4)
C1 C5 1.510(4)
C2 C3 1.518(4)
C2 H2 0.9300
C3 C4 1.541(4)
C3 C8 1.556(4)
C3 H3 0.9800
C4 C21 1.511(4)
C4 C5 1.550(4)
C4 H4 0.9800
C5 C6 1.510(4)
C5 H5 0.9800
C6 C7 1.315(4)
C6 H6 0.9300
C7 C8 1.523(5)
C8 C9 1.500(5)
C8 H8 0.9800
C9 C10 1.321(4)
C9 H9 0.9300
C10 C11 1.461(5)
C10 H10 0.9300
C11 C16 1.382(5)
C11 C12 1.390(5)
C12 C13 1.379(5)
C12 H12 0.9300
C13 C14 1.364(6)
C13 H13 0.9300
C14 C15 1.361(6)
C15 C16 1.376(6)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.491(5)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 C20 1.495(5)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 C26 1.388(4)
C21 C22 1.394(5)
C22 C23 1.378(5)
C22 H22 0.9300
C23 C24 1.375(5)
C23 H23 0.9300
C24 C25 1.371(5)
C25 C26 1.387(5)
C25 H25 0.9300
C26 H26 0.9300
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
C19 O1 C1 C2 -16.2(5)
C19 O1 C1 C5 171.4(3)
O1 C1 C2 C3 -173.9(3)
C5 C1 C2 C3 -1.4(4)
C1 C2 C3 C4 -27.0(3)
C1 C2 C3 C8 88.4(3)
C2 C3 C4 C21 -77.6(3)
C8 C3 C4 C21 163.9(3)
C2 C3 C4 C5 42.5(3)
C8 C3 C4 C5 -76.1(3)
C2 C1 C5 C6 -84.3(3)
O1 C1 C5 C6 89.7(3)
C2 C1 C5 C4 28.8(3)
O1 C1 C5 C4 -157.2(3)
C21 C4 C5 C6 -166.1(3)
C3 C4 C5 C6 70.0(3)
C21 C4 C5 C1 81.9(3)
C3 C4 C5 C1 -42.0(3)
C1 C5 C6 C7 71.1(4)
C4 C5 C6 C7 -35.5(4)
C5 C6 C7 O3 -171.3(3)
C5 C6 C7 C8 1.3(5)
C17 O3 C7 C6 -123.0(3)
C17 O3 C7 C8 63.8(4)
C6 C7 C8 C9 -131.5(4)
O3 C7 C8 C9 41.2(4)
C6 C7 C8 C3 -6.0(5)
O3 C7 C8 C3 166.8(3)
C2 C3 C8 C9 57.8(3)
C4 C3 C8 C9 169.3(3)
C2 C3 C8 C7 -66.3(3)
C4 C3 C8 C7 45.2(3)
C7 C8 C9 C10 -117.8(4)
C3 C8 C9 C10 119.0(4)
C8 C9 C10 C11 179.8(3)
C9 C10 C11 C16 -177.7(4)
C9 C10 C11 C12 1.2(6)
C16 C11 C12 C13 -0.1(6)
C10 C11 C12 C13 -179.1(4)
C11 C12 C13 C14 0.0(6)
C12 C13 C14 C15 0.0(6)
C12 C13 C14 Br1 180.0(3)
C13 C14 C15 C16 0.3(7)
Br1 C14 C15 C16 -179.7(3)
C14 C15 C16 C11 -0.5(7)
C12 C11 C16 C15 0.4(6)
C10 C11 C16 C15 179.4(4)
C7 O3 C17 O4 4.7(5)
C7 O3 C17 C18 -176.2(3)
C1 O1 C19 O2 -2.4(5)
C1 O1 C19 C20 177.9(3)
C3 C4 C21 C26 4.9(5)
C5 C4 C21 C26 -107.5(3)
C3 C4 C21 C22 -175.8(3)
C5 C4 C21 C22 71.7(4)
C26 C21 C22 C23 -0.5(5)
C4 C21 C22 C23 -179.8(3)
C21 C22 C23 C24 0.0(5)
C22 C23 C24 C25 0.6(5)
C22 C23 C24 Br2 -176.7(3)
C23 C24 C25 C26 -0.5(5)
Br2 C24 C25 C26 176.8(3)
C22 C21 C26 C25 0.6(5)
C4 C21 C26 C25 179.8(3)
C24 C25 C26 C21 -0.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095910
