#------------------------------------------------------------------------------
#$Date: 2015-12-03 13:26:14 +0200 (Thu, 03 Dec 2015) $
#$Revision: 170678 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/80/7118073.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_7118073
loop_
_publ_author_name
'Shivakrishna Kallepu'
'Krishna Kumar Gollapelli'
'Jagadeesh Babu Nanubolu'
'Rambabu Chegondi'
_publ_section_title
;
 Synthesis of highly strained bicyclic[3.n.1]alkenes by a metal-catalyzed
 Conia-ene reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              16840
_journal_paper_doi               10.1039/C5cc05926G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26
_chemical_name_systematic
5-methyl-2-phenylbicyclo[3.2.1]oct-2-ene-6,8-dione
_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-2014/7
_audit_update_record
;
2015-07-10 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.0820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4961(8)
_cell_length_b                   6.0394(4)
_cell_length_c                   16.0699(10)
_cell_measurement_reflns_used    7252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.61
_cell_volume                     1176.33(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         1.861
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0749P)²+0.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2535
_reflns_number_total             2830
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05926g2.cif
_cod_data_source_block           BA38M
_cod_database_code               7118073
_shelx_shelxl_version_number     2014/7
_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   0.960
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
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
_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 . . . . .
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
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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 .
