#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151818.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_7151818
loop_
_publ_author_name
'Bradley, Stephen A.'
'Bresnan, Brian J.'
'Draper, Sylvia M.'
'Geraghty, Niall W. A.'
'Jeffares, Mark'
'McCabe, Thomas'
'McMurry, T Brian H'
'O'Brien, John E'
_publ_section_title
;
 Photochemical [2 + 2] cycloaddition reactions of
 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation
 control to account for exceptions to the "rule of five".
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2959
_journal_page_last               2968
_journal_paper_doi               10.1039/c0ob01131b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.37
_space_group_IT_number           2
_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_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1beta3
_audit_creation_date             2001-10-10T12:14:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.769(8)
_cell_angle_beta                 96.613(10)
_cell_angle_gamma                103.792(8)
_cell_formula_units_Z            2
_cell_length_a                   6.6266(7)
_cell_length_b                   10.1023(10)
_cell_length_c                   12.3043(11)
_cell_measurement_temperature    293(2)
_cell_volume                     793.91(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2133
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.133
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1578
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01131b.txt
_cod_data_source_block           bscbs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               7151818
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.2442(2) 0.47824(14) 0.12640(11) 0.0561(4) Uani 1 1 d . . .
O2 O -0.0841(2) 0.20970(18) 0.13631(13) 0.0683(5) Uani 1 1 d . . .
O1 O 0.2688(3) 0.36697(17) -0.02735(13) 0.0677(5) Uani 1 1 d . . .
C6 C 0.2855(3) 0.25449(19) 0.14522(16) 0.0421(5) Uani 1 1 d . . .
C5 C 0.4742(3) 0.3077(2) 0.23437(18) 0.0480(6) Uani 1 1 d . . .
C4 C 0.4113(4) 0.3378(2) 0.34490(17) 0.0484(6) Uani 1 1 d . . .
C3 C 0.2645(3) 0.2162(2) 0.39009(16) 0.0454(5) Uani 1 1 d . . .
C2 C 0.3392(5) 0.0816(3) 0.3927(2) 0.0645(7) Uani 1 1 d . . .
C1 C 0.1519(4) 0.0118(2) 0.3101(2) 0.0609(7) Uani 1 1 d . . .
C9 C 0.1823(6) -0.0615(3) 0.2066(3) 0.0815(9) Uani 1 1 d . . .
C8 C 0.3522(6) 0.0104(3) 0.1390(3) 0.0808(10) Uani 1 1 d . . .
C7 C 0.3143(5) 0.1325(2) 0.0767(2) 0.0622(7) Uani 1 1 d . . .
C11 C 0.0781(3) 0.20702(19) 0.19210(16) 0.0437(5) Uani 1 1 d . . .
C10 C 0.0791(3) 0.1480(2) 0.30222(16) 0.0450(5) Uani 1 1 d . . .
C12 C 0.2639(3) 0.3693(2) 0.06946(17) 0.0463(5) Uani 1 1 d . . .
C13 C 0.2398(5) 0.6003(3) 0.0665(3) 0.0643(7) Uani 1 1 d . . .
C14 C 0.2032(4) 0.2602(2) 0.49729(16) 0.0516(6) Uani 1 1 d . . .
C15 C 0.0310(5) 0.3133(2) 0.5016(2) 0.0643(7) Uani 1 1 d . . .
C16 C -0.0143(7) 0.3630(3) 0.5991(3) 0.0857(9) Uani 1 1 d . . .
C17 C 0.1118(9) 0.3604(3) 0.6935(3) 0.1019(13) Uani 1 1 d . . .
C18 C 0.2829(8) 0.3098(4) 0.6921(2) 0.1027(13) Uani 1 1 d . . .
C19 C 0.3297(5) 0.2577(3) 0.5951(2) 0.0771(8) Uani 1 1 d . . .
H10 H -0.057(3) 0.1414(19) 0.3244(15) 0.045(5) Uiso 1 1 d . . .
H5A H 0.555(3) 0.235(2) 0.2402(17) 0.058(6) Uiso 1 1 d . . .
H5B H 0.561(3) 0.388(2) 0.2084(16) 0.055(6) Uiso 1 1 d . . .
H4A H 0.337(3) 0.417(2) 0.3390(16) 0.055(6) Uiso 1 1 d . . .
H4B H 0.536(4) 0.364(2) 0.3962(18) 0.057(6) Uiso 1 1 d . . .
H7A H 0.430(4) 0.167(2) 0.038(2) 0.070(7) Uiso 1 1 d . . .
H7B H 0.187(5) 0.104(3) 0.024(2) 0.090(10) Uiso 1 1 d . . .
H1 H 0.051(4) -0.051(2) 0.3470(18) 0.064(7) Uiso 1 1 d . . .
H2A H 0.475(4) 0.088(2) 0.366(2) 0.075(8) Uiso 1 1 d . . .
H2B H 0.344(4) 0.042(3) 0.462(2) 0.073(7) Uiso 1 1 d . . .
H15 H -0.059(4) 0.319(2) 0.437(2) 0.065(7) Uiso 1 1 d . . .
H8A H 0.366(4) -0.052(3) 0.084(2) 0.090(8) Uiso 1 1 d . . .
H8B H 0.490(5) 0.037(3) 0.190(3) 0.102(11) Uiso 1 1 d . . .
H19 H 0.453(4) 0.220(3) 0.589(2) 0.080(9) Uiso 1 1 d . . .
H9A H 0.032(5) -0.080(3) 0.163(3) 0.103(11) Uiso 1 1 d . . .
H9B H 0.215(4) -0.148(3) 0.230(2) 0.100(9) Uiso 1 1 d . . .
H13B H 0.182(6) 0.575(4) -0.015(3) 0.133(12) Uiso 1 1 d . . .
H13A H 0.374(6) 0.658(4) 0.076(3) 0.124(12) Uiso 1 1 d . . .
H13C H 0.124(7) 0.635(4) 0.089(3) 0.145(14) Uiso 1 1 d . . .
H18 H 0.374(6) 0.302(4) 0.751(3) 0.126(13) Uiso 1 1 d . . .
H16 H -0.147(6) 0.401(4) 0.595(3) 0.127(13) Uiso 1 1 d . . .
H17 H 0.085(5) 0.392(3) 0.766(3) 0.115(10) Uiso 1 1 d . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C12 O3 C13 117.04(18) . . ?
C12 C6 C11 107.22(16) . . ?
C12 C6 C7 108.90(17) . . ?
C11 C6 C7 106.80(18) . . ?
C12 C6 C5 108.91(16) . . ?
C11 C6 C5 113.17(16) . . ?
C7 C6 C5 111.67(19) . . ?
C4 C5 C6 113.58(18) . . ?
C5 C4 C3 113.79(19) . . ?
C14 C3 C4 109.11(17) . . ?
C14 C3 C2 115.08(18) . . ?
C4 C3 C2 115.42(19) . . ?
C14 C3 C10 115.47(17) . . ?
C4 C3 C10 111.32(16) . . ?
C2 C3 C10 89.44(16) . . ?
C1 C2 C3 90.89(18) . . ?
C9 C1 C2 121.0(3) . . ?
C9 C1 C10 120.0(2) . . ?
C2 C1 C10 90.02(16) . . ?
C1 C9 C8 118.3(2) . . ?
C7 C8 C9 117.2(3) . . ?
C8 C7 C6 116.8(2) . . ?
O2 C11 C10 121.55(19) . . ?
O2 C11 C6 119.53(18) . . ?
C10 C11 C6 118.74(18) . . ?
C11 C10 C3 116.69(17) . . ?
C11 C10 C1 114.82(17) . . ?
C3 C10 C1 89.55(16) . . ?
O1 C12 O3 123.2(2) . . ?
O1 C12 C6 126.11(19) . . ?
O3 C12 C6 110.62(17) . . ?
C15 C14 C19 117.2(3) . . ?
C15 C14 C3 122.2(2) . . ?
C19 C14 C3 120.4(2) . . ?
C14 C15 C16 121.7(3) . . ?
C17 C16 C15 120.2(4) . . ?
C18 C17 C16 119.7(3) . . ?
C17 C18 C19 121.0(3) . . ?
C14 C19 C18 120.2(4) . . ?
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
O3 C12 1.337(2) . ?
O3 C13 1.449(3) . ?
O2 C11 1.213(2) . ?
O1 C12 1.195(2) . ?
C6 C12 1.520(3) . ?
C6 C11 1.526(3) . ?
C6 C7 1.545(3) . ?
C6 C5 1.550(3) . ?
C5 C4 1.515(3) . ?
C4 C3 1.529(3) . ?
C3 C14 1.516(3) . ?
C3 C2 1.554(3) . ?
C3 C10 1.557(3) . ?
C2 C1 1.531(4) . ?
C1 C9 1.522(3) . ?
C1 C10 1.564(3) . ?
C9 C8 1.526(4) . ?
C8 C7 1.518(4) . ?
C11 C10 1.487(3) . ?
C14 C15 1.378(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.386(4) . ?
C16 C17 1.355(5) . ?
C17 C18 1.352(5) . ?
C18 C19 1.394(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26995945
2 PubChem 139190640
