#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151817.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_7151817
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            'C18 H20 O3'
_chemical_formula_weight         284.34
_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                102.795(8)
_cell_angle_beta                 99.112(11)
_cell_angle_gamma                105.356(9)
_cell_formula_units_Z            2
_cell_length_a                   6.6572(9)
_cell_length_b                   9.8399(8)
_cell_length_c                   12.3209(15)
_cell_measurement_temperature    293(2)
_cell_volume                     738.47(16)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    Shelxtl
_computing_publication_material  Shelxtl
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2763
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                1396
_reflns_number_total             2529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01131b.txt
_cod_data_source_block           mcmcs
_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_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        738.47(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151817
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
O2 O 0.7039(4) 0.4912(2) 0.85995(18) 0.0592(6) Uani 1 1 d . . .
O3 O 1.0758(3) 0.7487(2) 0.85689(17) 0.0540(6) Uani 1 1 d . . .
C1 C 0.7874(5) 0.9930(3) 0.7799(3) 0.0498(8) Uani 1 1 d . . .
C2 C 0.9085(5) 0.8787(3) 0.7491(2) 0.0411(7) Uani 1 1 d . . .
C3 C 0.9182(4) 0.7822(3) 0.8251(2) 0.0377(6) Uani 1 1 d . . .
C4 C 0.7099(4) 0.7317(3) 0.8622(2) 0.0383(7) Uani 1 1 d . . .
C5 C 0.5167(5) 0.6683(3) 0.7568(2) 0.0437(7) Uani 1 1 d . . .
C6 C 0.5833(5) 0.6578(3) 0.6430(3) 0.0454(7) Uani 1 1 d . . .
C7 C 0.7344(4) 0.8013(3) 0.6340(2) 0.0413(7) Uani 1 1 d . . .
C8 C 0.6473(6) 0.9346(4) 0.6577(3) 0.0563(9) Uani 1 1 d . . .
C9 C 0.6708(6) 0.9856(4) 0.8781(3) 0.0549(9) Uani 1 1 d . . .
C10 C 0.6976(6) 0.8732(3) 0.9416(3) 0.0506(8) Uani 1 1 d . . .
C11 C 0.7300(5) 0.6225(3) 0.9294(3) 0.0471(7) Uani 1 1 d . . .
C12 C 0.7199(6) 0.3774(4) 0.9134(3) 0.0760(11) Uani 1 1 d . . .
H12A H 0.8675 0.3928 0.9464 0.114 Uiso 1 1 calc R . .
H12B H 0.6618 0.2838 0.8572 0.114 Uiso 1 1 calc R . .
H12C H 0.6411 0.3796 0.9723 0.114 Uiso 1 1 calc R . .
C13 C 0.8166(5) 0.7693(3) 0.5268(2) 0.0446(7) Uani 1 1 d . . .
C14 C 0.7222(6) 0.7913(4) 0.4269(3) 0.0608(9) Uani 1 1 d . . .
C15 C 0.7899(7) 0.7504(4) 0.3268(3) 0.0725(11) Uani 1 1 d . . .
C16 C 0.9495(7) 0.6879(4) 0.3256(3) 0.0681(10) Uani 1 1 d . . .
C17 C 1.0459(6) 0.6671(4) 0.4243(3) 0.0687(10) Uani 1 1 d . . .
C18 C 0.9802(5) 0.7077(4) 0.5244(3) 0.0583(9) Uani 1 1 d . . .
H1 H 0.884(5) 1.093(3) 0.796(2) 0.055(8) Uiso 1 1 d . . .
H2 H 1.048(4) 0.928(3) 0.7394(19) 0.036(7) Uiso 1 1 d . . .
H5A H 0.442(4) 0.568(3) 0.754(2) 0.045(7) Uiso 1 1 d . . .
H5B H 0.422(4) 0.729(3) 0.763(2) 0.048(8) Uiso 1 1 d . . .
H6A H 0.654(4) 0.576(3) 0.629(2) 0.051(8) Uiso 1 1 d . . .
H6B H 0.455(5) 0.625(3) 0.581(2) 0.058(9) Uiso 1 1 d . . .
H8A H 0.504(5) 0.908(3) 0.647(2) 0.050(9) Uiso 1 1 d . . .
H8B H 0.689(6) 0.993(4) 0.608(3) 0.084(12) Uiso 1 1 d . . .
H9A H 0.717(5) 1.078(4) 0.930(3) 0.065(10) Uiso 1 1 d . . .
H9B H 0.521(5) 0.972(3) 0.844(2) 0.066(10) Uiso 1 1 d . . .
H10A H 0.832(5) 0.915(3) 1.005(2) 0.057(9) Uiso 1 1 d . . .
H10B H 0.586(6) 0.845(3) 0.977(3) 0.075(11) Uiso 1 1 d . . .
H14 H 0.600(5) 0.831(3) 0.424(2) 0.064(10) Uiso 1 1 d . . .
H15 H 0.726(5) 0.772(3) 0.264(3) 0.064(9) Uiso 1 1 d . . .
H16 H 0.993(6) 0.656(4) 0.249(3) 0.101(12) Uiso 1 1 d . . .
H17 H 1.158(6) 0.616(4) 0.421(3) 0.099(13) Uiso 1 1 d . . .
H18 H 1.059(5) 0.695(3) 0.597(3) 0.065(9) Uiso 1 1 d . . .
O1 O 0.7681(4) 0.6501(3) 1.03156(19) 0.0720(7) Uani 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 0.0000 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
C11 O2 C12 116.6(2) . . ?
C8 C1 C9 116.9(3) . . ?
C8 C1 C2 89.4(2) . . ?
C9 C1 C2 117.7(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 C7 113.1(2) . . ?
C1 C2 C7 89.3(2) . . ?
O3 C3 C2 124.1(3) . . ?
O3 C3 C4 123.1(2) . . ?
C2 C3 C4 112.7(2) . . ?
C11 C4 C3 108.3(2) . . ?
C11 C4 C10 110.0(2) . . ?
C3 C4 C10 103.7(2) . . ?
C11 C4 C5 113.0(2) . . ?
C3 C4 C5 110.6(2) . . ?
C10 C4 C5 110.9(2) . . ?
C6 C5 C4 113.2(2) . . ?
C5 C6 C7 114.8(2) . . ?
C13 C7 C6 109.0(2) . . ?
C13 C7 C8 117.8(2) . . ?
C6 C7 C8 114.3(3) . . ?
C13 C7 C2 116.3(2) . . ?
C6 C7 C2 109.8(2) . . ?
C8 C7 C2 88.4(2) . . ?
C1 C8 C7 90.9(2) . . ?
C10 C9 C1 116.2(3) . . ?
C9 C10 C4 112.5(3) . . ?
O1 C11 O2 124.0(3) . . ?
O1 C11 C4 124.9(3) . . ?
O2 C11 C4 111.1(3) . . ?
C14 C13 C18 118.1(3) . . ?
C14 C13 C7 121.3(3) . . ?
C18 C13 C7 120.5(3) . . ?
C13 C14 C15 120.3(4) . . ?
C16 C15 C14 120.8(4) . . ?
C15 C16 C17 119.4(4) . . ?
C16 C17 C18 120.3(4) . . ?
C13 C18 C17 121.1(3) . . ?
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
O2 C11 1.332(3) . ?
O2 C12 1.438(3) . ?
O3 C3 1.214(3) . ?
C1 C8 1.535(5) . ?
C1 C9 1.542(4) . ?
C1 C2 1.565(4) . ?
C2 C3 1.479(4) . ?
C2 C7 1.571(4) . ?
C3 C4 1.521(4) . ?
C4 C11 1.515(4) . ?
C4 C10 1.544(4) . ?
C4 C5 1.555(4) . ?
C5 C6 1.527(4) . ?
C6 C7 1.539(4) . ?
C7 C13 1.510(4) . ?
C7 C8 1.558(4) . ?
C9 C10 1.521(4) . ?
C11 O1 1.197(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.380(4) . ?
C14 C15 1.391(5) . ?
C15 C16 1.362(5) . ?
C16 C17 1.365(5) . ?
C17 C18 1.385(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26995944
2 PubChem 53359652
