#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504645.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_1504645
loop_
_publ_author_name
'Ko, Changhong'
'Feltenberger, John B.'
'Ghosh, Sunil K.'
'Hsung, Richard P.'
_publ_section_title
;
 Gassman's intramolecular [2 + 2] cationic cycloaddition. formal total
 syntheses of raikovenal and epi-raikovenal.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              1971
_journal_page_last               1974
_journal_paper_doi               10.1021/ol8004968
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C17 H21 Br O3'
_chemical_formula_sum            'C17 H21 Br O3'
_chemical_formula_weight         353.25
_chemical_name_common            05350
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.308(2)
_cell_angle_beta                 96.276(2)
_cell_angle_gamma                93.402(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0187(6)
_cell_length_b                   7.9272(7)
_cell_length_c                   14.4217(13)
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.58
_cell_volume                     794.52(12)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6652
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  0.8812
_exptl_absorpt_correction_T_min  0.5099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.3186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2184
_reflns_number_total             2799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8004968-file005.cif
_cod_data_source_block           05350
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504645
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.57258(6) 0.52090(5) 0.72915(3) 0.03775(16) Uani 1 1 d .
O1 O 0.9196(3) -0.4039(3) 0.09612(17) 0.0315(6) Uani 1 1 d .
O2 O 0.9390(3) 0.0992(3) 0.37235(16) 0.0270(6) Uani 1 1 d .
O3 O 1.2194(3) 0.1994(3) 0.45141(17) 0.0345(6) Uani 1 1 d .
C1 C 0.7614(5) -0.3796(4) 0.0282(3) 0.0320(9) Uani 1 1 d .
H1A H 0.6814 -0.4870 0.0143 0.038 Uiso 1 1 calc R
H1B H 0.8096 -0.3458 -0.0304 0.038 Uiso 1 1 calc R
C2 C 0.6418(5) -0.2440(4) 0.0649(3) 0.0308(9) Uani 1 1 d .
H2A H 0.5935 -0.2788 0.1233 0.037 Uiso 1 1 calc R
H2B H 0.5294 -0.2314 0.0185 0.037 Uiso 1 1 calc R
C3 C 0.7578(5) -0.0735(4) 0.0840(2) 0.0226(8) Uani 1 1 d .
H3 H 0.7526 -0.0038 0.0283 0.027 Uiso 1 1 calc R
C4 C 0.9661(5) -0.0971(4) 0.1276(2) 0.0217(7) Uani 1 1 d .
H4 H 1.0525 -0.0003 0.1121 0.026 Uiso 1 1 calc R
C5 C 1.0535(5) -0.2607(4) 0.1035(3) 0.0270(8) Uani 1 1 d .
H5A H 1.1080 -0.2521 0.0433 0.032 Uiso 1 1 calc R
H5B H 1.1603 -0.2777 0.1521 0.032 Uiso 1 1 calc R
C6 C 0.7264(5) 0.0304(4) 0.1760(2) 0.0219(8) Uani 1 1 d .
C7 C 0.5350(5) 0.0053(5) 0.2161(3) 0.0318(9) Uani 1 1 d .
H7A H 0.4316 0.0413 0.1719 0.048 Uiso 1 1 calc R
H7B H 0.5401 0.0730 0.2755 0.048 Uiso 1 1 calc R
H7C H 0.5105 -0.1147 0.2268 0.048 Uiso 1 1 calc R
C8 C 0.7717(5) 0.2195(4) 0.1675(3) 0.0298(9) Uani 1 1 d .
H8A H 0.6682 0.2647 0.1270 0.045 Uiso 1 1 calc R
H8B H 0.8931 0.2363 0.1406 0.045 Uiso 1 1 calc R
H8C H 0.7827 0.2787 0.2296 0.045 Uiso 1 1 calc R
C9 C 0.9004(5) -0.0576(4) 0.2250(2) 0.0213(7) Uani 1 1 d .
H9 H 0.8530 -0.1651 0.2504 0.026 Uiso 1 1 calc R
C10 C 1.0429(5) 0.0380(4) 0.2969(2) 0.0248(8) Uani 1 1 d .
H10A H 1.1422 -0.0372 0.3209 0.030 Uiso 1 1 calc R
H10B H 1.1070 0.1343 0.2692 0.030 Uiso 1 1 calc R
C11 C 1.0463(5) 0.1842(4) 0.4450(2) 0.0230(8) Uani 1 1 d .
C12 C 0.9274(5) 0.2595(4) 0.5141(2) 0.0227(8) Uani 1 1 d .
C13 C 1.0200(5) 0.3524(4) 0.5923(2) 0.0252(8) Uani 1 1 d .
H13 H 1.1564 0.3641 0.6012 0.030 Uiso 1 1 calc R
C14 C 0.9166(5) 0.4279(4) 0.6571(2) 0.0278(8) Uani 1 1 d .
H14 H 0.9805 0.4899 0.7111 0.033 Uiso 1 1 calc R
C15 C 0.7182(5) 0.4118(4) 0.6423(2) 0.0271(8) Uani 1 1 d .
C16 C 0.6228(5) 0.3203(5) 0.5653(3) 0.0348(9) Uani 1 1 d .
H16 H 0.4864 0.3104 0.5563 0.042 Uiso 1 1 calc R
C17 C 0.7284(5) 0.2428(5) 0.5013(3) 0.0322(9) Uani 1 1 d .
H17 H 0.6642 0.1780 0.4483 0.039 Uiso 1 1 calc R
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
C1 O1 C5 109.8(3)
C11 O2 C10 115.8(2)
O1 C1 C2 109.8(3)
O1 C1 H1A 109.7
C2 C1 H1A 109.7
O1 C1 H1B 109.7
C2 C1 H1B 109.7
H1A C1 H1B 108.2
C1 C2 C3 111.6(3)
C1 C2 H2A 109.3
C3 C2 H2A 109.3
C1 C2 H2B 109.3
C3 C2 H2B 109.3
H2A C2 H2B 108.0
C2 C3 C4 111.1(3)
C2 C3 C6 116.1(3)
C4 C3 C6 88.3(2)
C2 C3 H3 113.0
C4 C3 H3 113.0
C6 C3 H3 113.0
C5 C4 C9 121.8(3)
C5 C4 C3 118.0(3)
C9 C4 C3 88.3(2)
C5 C4 H4 109.0
C9 C4 H4 109.0
C3 C4 H4 109.0
O1 C5 C4 113.2(3)
O1 C5 H5A 108.9
C4 C5 H5A 108.9
O1 C5 H5B 108.9
C4 C5 H5B 108.9
H5A C5 H5B 107.8
C8 C6 C7 109.1(3)
C8 C6 C3 110.8(3)
C7 C6 C3 119.0(3)
C8 C6 C9 112.5(3)
C7 C6 C9 116.8(3)
C3 C6 C9 87.3(2)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C4 117.1(3)
C10 C9 C6 121.0(3)
C4 C9 C6 88.6(2)
C10 C9 H9 109.5
C4 C9 H9 109.5
C6 C9 H9 109.5
O2 C10 C9 107.6(3)
O2 C10 H10A 110.2
C9 C10 H10A 110.2
O2 C10 H10B 110.2
C9 C10 H10B 110.2
H10A C10 H10B 108.5
O3 C11 O2 123.0(3)
O3 C11 C12 124.6(3)
O2 C11 C12 112.4(3)
C17 C12 C13 119.5(3)
C17 C12 C11 122.0(3)
C13 C12 C11 118.5(3)
C14 C13 C12 120.7(3)
C14 C13 H13 119.6
C12 C13 H13 119.6
C13 C14 C15 118.9(3)
C13 C14 H14 120.6
C15 C14 H14 120.6
C16 C15 C14 121.5(3)
C16 C15 Br1 119.0(3)
C14 C15 Br1 119.5(3)
C15 C16 C17 119.1(3)
C15 C16 H16 120.4
C17 C16 H16 120.4
C16 C17 C12 120.3(3)
C16 C17 H17 119.9
C12 C17 H17 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.903(3)
O1 C1 1.428(4)
O1 C5 1.421(4)
O2 C11 1.343(4)
O2 C10 1.450(4)
O3 C11 1.207(4)
C1 C2 1.510(5)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.530(5)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.554(5)
C3 C6 1.564(4)
C3 H3 1.0000
C4 C5 1.506(5)
C4 C9 1.547(4)
C4 H4 1.0000
C5 H5A 0.9900
C5 H5B 0.9900
C6 C8 1.528(5)
C6 C7 1.527(4)
C6 C9 1.564(5)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.498(5)
C9 H9 1.0000
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.490(5)
C12 C17 1.386(5)
C12 C13 1.387(5)
C13 C14 1.376(5)
C13 H13 0.9500
C14 C15 1.383(5)
C14 H14 0.9500
C15 C16 1.376(5)
C16 C17 1.385(5)
C16 H16 0.9500
C17 H17 0.9500
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
C5 O1 C1 C2 -70.1(3)
O1 C1 C2 C3 61.4(4)
C1 C2 C3 C4 -39.4(4)
C1 C2 C3 C6 -138.3(3)
C2 C3 C4 C5 28.7(4)
C6 C3 C4 C5 146.1(3)
C2 C3 C4 C9 -96.7(3)
C6 C3 C4 C9 20.6(2)
C1 O1 C5 C4 56.9(4)
C9 C4 C5 O1 69.5(4)
C3 C4 C5 O1 -37.3(4)
C2 C3 C6 C8 -154.6(3)
C4 C3 C6 C8 92.6(3)
C2 C3 C6 C7 -26.9(4)
C4 C3 C6 C7 -139.7(3)
C2 C3 C6 C9 92.4(3)
C4 C3 C6 C9 -20.4(2)
C5 C4 C9 C10 92.6(4)
C3 C4 C9 C10 -145.2(3)
C5 C4 C9 C6 -142.8(3)
C3 C4 C9 C6 -20.6(2)
C8 C6 C9 C10 30.2(4)
C7 C6 C9 C10 -97.0(4)
C3 C6 C9 C10 141.6(3)
C8 C6 C9 C4 -90.9(3)
C7 C6 C9 C4 141.8(3)
C3 C6 C9 C4 20.5(2)
C11 O2 C10 C9 178.1(3)
C4 C9 C10 O2 165.3(3)
C6 C9 C10 O2 59.3(4)
C10 O2 C11 O3 -5.2(5)
C10 O2 C11 C12 173.5(3)
O3 C11 C12 C17 177.6(3)
O2 C11 C12 C17 -1.0(5)
O3 C11 C12 C13 -0.7(5)
O2 C11 C12 C13 -179.4(3)
C17 C12 C13 C14 0.1(5)
C11 C12 C13 C14 178.5(3)
C12 C13 C14 C15 -1.0(5)
C13 C14 C15 C16 1.0(5)
C13 C14 C15 Br1 -178.1(3)
C14 C15 C16 C17 -0.1(6)
Br1 C15 C16 C17 179.0(3)
C15 C16 C17 C12 -0.9(6)
C13 C12 C17 C16 0.9(5)
C11 C12 C17 C16 -177.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101868984
