# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BA38M
_database_code_depnum_ccdc_archive 'CCDC 1412029'
_audit_update_record             
;
2015-07-10 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-phenylbicyclo[3.2.1]oct-2-ene-6,8-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   12.4961(8)
_cell_length_b                   6.0394(4)
_cell_length_c                   16.0699(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.0820(10)
_cell_angle_gamma                90
_cell_volume                     1176.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7252
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.22

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13090
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2830
_reflns_number_gt                2535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+0.2197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2830
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 1.05858(8) 0.79739(17) 0.15472(7) 0.0338(2) Uani 1 1 d . . . . .
C2 C 1.05433(9) 0.70839(17) 0.24249(7) 0.0368(2) Uani 1 1 d . . . . .
H2A H 1.1155 0.6087 0.2647 0.044 Uiso 1 1 calc R U . . .
H2B H 0.9856 0.6306 0.2397 0.044 Uiso 1 1 calc R U . . .
C3 C 1.06275(8) 0.91718(18) 0.29863(6) 0.0332(2) Uani 1 1 d . . . . .
H3 H 1.0984 0.8888 0.3591 0.040 Uiso 1 1 calc R U . . .
C4 C 1.12824(8) 1.07465(17) 0.25653(7) 0.0324(2) Uani 1 1 d . . . . .
C5 C 1.08176(8) 1.04566(17) 0.16098(6) 0.0322(2) Uani 1 1 d . . . . .
C6 C 1.15053(10) 1.1321(2) 0.10243(8) 0.0433(3) Uani 1 1 d . . . . .
H6A H 1.1717 1.2824 0.1175 0.065 Uiso 1 1 calc R U . . .
H6B H 1.1081 1.1264 0.0440 0.065 Uiso 1 1 calc R U . . .
H6C H 1.2154 1.0424 0.1087 0.065 Uiso 1 1 calc R U . . .
C7 C 0.96652(9) 1.16138(18) 0.14308(7) 0.0362(2) Uani 1 1 d . . . . .
H7A H 0.9765 1.3189 0.1359 0.043 Uiso 1 1 calc R U . . .
H7B H 0.9211 1.1051 0.0895 0.043 Uiso 1 1 calc R U . . .
C8 C 0.90650(9) 1.12826(19) 0.21235(7) 0.0382(3) Uani 1 1 d . . . . .
H8 H 0.8354 1.1848 0.2034 0.046 Uiso 1 1 calc R U . . .
C9 C 0.94880(9) 1.02252(18) 0.28612(7) 0.0345(2) Uani 1 1 d . . . . .
C10 C 0.88829(9) 0.9897(2) 0.35393(7) 0.0399(3) Uani 1 1 d . . . . .
C11 C 0.90815(12) 0.8076(3) 0.40782(9) 0.0534(3) Uani 1 1 d . . . . .
H11 H 0.9618 0.7055 0.4025 0.064 Uiso 1 1 calc R U . . .
C12 C 0.84902(13) 0.7748(3) 0.46984(10) 0.0654(4) Uani 1 1 d . . . . .
H12 H 0.8634 0.6510 0.5052 0.078 Uiso 1 1 calc R U . . .
C13 C 0.77026(12) 0.9225(3) 0.47932(10) 0.0637(4) Uani 1 1 d . . . . .
H13 H 0.7312 0.9004 0.5210 0.076 Uiso 1 1 calc R U . . .
C14 C 0.74933(12) 1.1045(3) 0.42643(10) 0.0661(4) Uani 1 1 d . . . . .
H14 H 0.6953 1.2051 0.4322 0.079 Uiso 1 1 calc R U . . .
C15 C 0.80797(11) 1.1395(3) 0.36464(9) 0.0548(3) Uani 1 1 d . . . . .
H15 H 0.7935 1.2645 0.3299 0.066 Uiso 1 1 calc R U . . .
O1 O 1.04456(8) 0.69075(15) 0.08992(6) 0.0504(3) Uani 1 1 d . . . . .
O2 O 1.19914(7) 1.20196(15) 0.29162(6) 0.0449(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 O1 1.2005(13) . ?
C1 C2 1.5223(15) . ?
C1 C5 1.5258(14) . ?
C2 C3 1.5391(15) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5171(14) . ?
C3 C9 1.5276(14) . ?
C3 H3 0.9800 . ?
C4 O2 1.2046(13) . ?
C4 C5 1.5138(14) . ?
C5 C6 1.5134(14) . ?
C5 C7 1.5630(14) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.4993(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.3370(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.4830(15) . ?
C10 C11 1.3848(19) . ?
C10 C15 1.3923(17) . ?
C11 C12 1.3918(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.3862(19) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
O1 C1 C2 125.71(10) . . ?
O1 C1 C5 124.73(10) . . ?
C2 C1 C5 109.56(8) . . ?
C1 C2 C3 103.94(8) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C9 105.48(8) . . ?
C4 C3 C2 102.68(8) . . ?
C9 C3 C2 109.60(8) . . ?
C4 C3 H3 112.8 . . ?
C9 C3 H3 112.8 . . ?
C2 C3 H3 112.8 . . ?
O2 C4 C5 127.28(10) . . ?
O2 C4 C3 127.33(10) . . ?
C5 C4 C3 105.33(8) . . ?
C6 C5 C4 117.06(9) . . ?
C6 C5 C1 115.18(9) . . ?
C4 C5 C1 101.56(8) . . ?
C6 C5 C7 111.62(9) . . ?
C4 C5 C7 104.12(8) . . ?
C1 C5 C7 106.00(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 114.12(9) . . ?
C8 C7 H7A 108.7 . . ?
C5 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C5 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 124.11(10) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C8 C9 C10 123.58(10) . . ?
C8 C9 C3 118.06(9) . . ?
C10 C9 C3 118.25(9) . . ?
C11 C10 C15 117.62(12) . . ?
C11 C10 C9 121.32(11) . . ?
C15 C10 C9 121.06(12) . . ?
C10 C11 C12 121.01(14) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.68(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.18(13) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 120.69(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.81(15) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
