 
data_xr181full
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C12 H12 O2'
_chemical_formula_sum             'C12 H12 O2' 
_chemical_formula_weight          188.22

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            9
_space_group_name_H-M_alt         'C c'
_space_group_name_Hall            'C -2yc'
 
_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, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    10.7797(7)
_cell_length_b                    21.3371(13)
_cell_length_c                    8.7302(5)
_cell_angle_alpha                 90
_cell_angle_beta                  102.503(3)
_cell_angle_gamma                 90
_cell_volume                      1960.4(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     1864
_cell_measurement_theta_min       2.89
_cell_measurement_theta_max       20.76
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.275          
_exptl_crystal_F_000              800
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.280
_exptl_crystal_size_min           0.050
_exptl_absorpt_coefficient_mu     0.086
_shelx_estimated_absorpt_T_min    0.975
_shelx_estimated_absorpt_T_max    0.996
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5288  
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10554
_diffrn_reflns_av_unetI/netI      0.1273
_diffrn_reflns_av_R_equivalents   0.1426
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -25
_diffrn_reflns_limit_k_max        25
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.158
_diffrn_reflns_theta_max          24.984
_diffrn_reflns_theta_full         24.984
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3397
_reflns_number_gt                 1890
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.994
_reflns_Friedel_fraction_max      1.000
_reflns_Friedel_fraction_full     1.000
 
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0381P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    -1(3)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          3397
_refine_ls_number_parameters      262
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1055
_refine_ls_R_factor_gt            0.0632
_refine_ls_wR_factor_ref          0.1442
_refine_ls_wR_factor_gt           0.1231
_refine_ls_goodness_of_fit_ref    1.027
_refine_ls_restrained_S_all       1.027
_refine_ls_shift/su_max           0.001
_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
O1B O -0.1585(4) 1.0281(2) -0.0686(6) 0.0558(13) Uani 1 1 d . . . . .
O2B O -0.2597(5) 0.9599(3) 0.0553(6) 0.0599(13) Uani 1 1 d D . . . .
C1B C -0.0978(6) 0.9228(3) -0.0641(8) 0.0435(18) Uani 1 1 d . . . . .
C2B C 0.0137(6) 0.9317(3) -0.1415(8) 0.0472(19) Uani 1 1 d . . . . .
H2B1 H 0.049751 0.974550 -0.129234 0.057 Uiso 1 1 calc R U . . .
H2B2 H -0.004033 0.918530 -0.252815 0.057 Uiso 1 1 calc R U . . .
C3B C 0.0928(6) 0.8827(3) -0.0268(8) 0.0469(18) Uani 1 1 d . . . . .
H3B H 0.109240 0.843705 -0.082761 0.056 Uiso 1 1 calc R U . . .
C4B C -0.0202(6) 0.8754(3) 0.0501(8) 0.0454(18) Uani 1 1 d . . . . .
H4B H -0.012702 0.877222 0.166200 0.054 Uiso 1 1 calc R U . . .
C5B C -0.1347(6) 0.8555(4) -0.0585(10) 0.059(2) Uani 1 1 d . . . . .
H5B1 H -0.209788 0.845698 -0.014672 0.070 Uiso 1 1 calc R U . . .
H5B2 H -0.124612 0.828377 -0.147048 0.070 Uiso 1 1 calc R U . . .
C6B C 0.2128(5) 0.9085(3) 0.0755(8) 0.0469(18) Uani 1 1 d . . . . .
C7B C 0.2100(7) 0.9608(4) 0.1703(9) 0.059(2) Uani 1 1 d . . . . .
H7B H 0.131008 0.979981 0.173012 0.071 Uiso 1 1 calc R U . . .
C8B C 0.3185(7) 0.9845(4) 0.2583(9) 0.069(2) Uani 1 1 d . . . . .
H8B H 0.314419 1.021091 0.318855 0.082 Uiso 1 1 calc R U . . .
C9B C 0.4355(7) 0.9569(4) 0.2629(10) 0.066(2) Uani 1 1 d . . . . .
H9B H 0.510287 0.972778 0.329871 0.079 Uiso 1 1 calc R U . . .
C10B C 0.4405(7) 0.9055(4) 0.1671(10) 0.062(2) Uani 1 1 d . . . . .
H10B H 0.520182 0.887414 0.162555 0.075 Uiso 1 1 calc R U . . .
C11B C 0.3312(6) 0.8810(4) 0.0795(9) 0.056(2) Uani 1 1 d . . . . .
H11B H 0.335570 0.844271 0.019434 0.067 Uiso 1 1 calc R U . . .
C12B C -0.1774(6) 0.9740(4) -0.0254(8) 0.0423(17) Uani 1 1 d . . . . .
O1A O 0.6390(4) 0.9402(3) 0.6572(6) 0.0519(13) Uani 1 1 d . . . . .
O2A O 0.7101(4) 0.8774(2) 0.4889(6) 0.0548(14) Uani 1 1 d . . . . .
C1A C 0.5952(6) 0.8327(3) 0.6653(8) 0.0429(17) Uani 1 1 d . . . . .
C2A C 0.5115(6) 0.8352(3) 0.7835(9) 0.053(2) Uani 1 1 d . . . . .
H2A1 H 0.466910 0.875681 0.784416 0.064 Uiso 1 1 calc R U . . .
H2A2 H 0.556041 0.823191 0.890928 0.064 Uiso 1 1 calc R U . . .
C3A C 0.4252(6) 0.7823(3) 0.6951(8) 0.0459(18) Uani 1 1 d . . . . .
H3A H 0.436990 0.742488 0.757039 0.055 Uiso 1 1 calc R U . . .
C4A C 0.5073(6) 0.7820(3) 0.5691(9) 0.0473(19) Uani 1 1 d . . . . .
H4A H 0.472716 0.783724 0.453246 0.057 Uiso 1 1 calc R U . . .
C5A C 0.6421(7) 0.7680(4) 0.6449(10) 0.059(2) Uani 1 1 d . . . . .
H5A1 H 0.702926 0.762897 0.575562 0.071 Uiso 1 1 calc R U . . .
H5A2 H 0.657773 0.740049 0.737622 0.071 Uiso 1 1 calc R U . . .
C6A C 0.2872(6) 0.7968(4) 0.6387(8) 0.0489(19) Uani 1 1 d . . . . .
C7A C 0.1961(6) 0.7576(4) 0.6784(8) 0.053(2) Uani 1 1 d . . . . .
H7A H 0.221554 0.721197 0.739790 0.064 Uiso 1 1 calc R U . . .
C8A C 0.0689(7) 0.7716(5) 0.6289(9) 0.065(2) Uani 1 1 d . . . . .
H8A H 0.007506 0.744277 0.656305 0.078 Uiso 1 1 calc R U . . .
C9A C 0.0296(7) 0.8233(5) 0.5421(10) 0.071(3) Uani 1 1 d . . . . .
H9A H -0.058548 0.832136 0.509426 0.085 Uiso 1 1 calc R U . . .
C10A C 0.1184(7) 0.8633(4) 0.5012(9) 0.063(2) Uani 1 1 d . . . . .
H10A H 0.091715 0.899731 0.440542 0.076 Uiso 1 1 calc R U . . .
C11A C 0.2475(7) 0.8494(4) 0.5500(9) 0.0549(19) Uani 1 1 d . . . . .
H11A H 0.308733 0.876566 0.521722 0.066 Uiso 1 1 calc R U . . .
C12A C 0.6504(6) 0.8878(4) 0.6001(8) 0.0463(19) Uani 1 1 d . . . . .
H2A H 0.748(11) 0.912(7) 0.459(15) 0.19(6) Uiso 1 1 d . . . . .
H2B H -0.322(9) 0.981(6) 0.076(17) 0.20(6) Uiso 1 1 d 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
O1B C12B 1.246(8) . ?
O2B C12B 1.282(8) . ?
C1B C12B 1.474(9) . ?
C1B C5B 1.493(10) . ?
C1B C2B 1.512(8) . ?
C1B C4B 1.534(10) . ?
C2B C3B 1.566(9) . ?
C3B C6B 1.507(9) . ?
C3B C4B 1.522(8) . ?
C4B C5B 1.447(9) . ?
C6B C7B 1.394(9) . ?
C6B C11B 1.398(9) . ?
C7B C8B 1.351(10) . ?
C8B C9B 1.383(10) . ?
C9B C10B 1.388(11) . ?
C10B C11B 1.363(9) . ?
O1A C12A 1.243(8) . ?
O2A C12A 1.295(8) . ?
C1A C12A 1.486(10) . ?
C1A C5A 1.493(9) . ?
C1A C2A 1.511(9) . ?
C1A C4A 1.557(9) . ?
C2A C3A 1.556(9) . ?
C3A C6A 1.495(9) . ?
C3A C4A 1.554(9) . ?
C4A C5A 1.491(10) . ?
C6A C11A 1.378(9) . ?
C6A C7A 1.390(9) . ?
C7A C8A 1.378(9) . ?
C8A C9A 1.354(11) . ?
C9A C10A 1.386(11) . ?
C10A C11A 1.396(9) . ?
 
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
C12B C1B C5B 122.2(6) . . ?
C12B C1B C2B 124.6(6) . . ?
C5B C1B C2B 112.3(6) . . ?
C12B C1B C4B 127.0(6) . . ?
C5B C1B C4B 57.1(5) . . ?
C2B C1B C4B 90.0(5) . . ?
C1B C2B C3B 90.3(5) . . ?
C6B C3B C4B 116.2(6) . . ?
C6B C3B C2B 114.5(6) . . ?
C4B C3B C2B 88.4(5) . . ?
C5B C4B C3B 113.1(6) . . ?
C5B C4B C1B 60.0(5) . . ?
C3B C4B C1B 91.2(5) . . ?
C4B C5B C1B 62.9(5) . . ?
C7B C6B C11B 117.2(6) . . ?
C7B C6B C3B 121.2(6) . . ?
C11B C6B C3B 121.6(7) . . ?
C8B C7B C6B 120.7(7) . . ?
C7B C8B C9B 121.9(8) . . ?
C8B C9B C10B 118.2(7) . . ?
C11B C10B C9B 120.0(7) . . ?
C10B C11B C6B 121.8(7) . . ?
O1B C12B O2B 124.2(7) . . ?
O1B C12B C1B 118.4(6) . . ?
O2B C12B C1B 117.3(7) . . ?
C12A C1A C5A 120.7(6) . . ?
C12A C1A C2A 125.6(6) . . ?
C5A C1A C2A 112.5(6) . . ?
C12A C1A C4A 126.1(6) . . ?
C5A C1A C4A 58.5(4) . . ?
C2A C1A C4A 90.6(5) . . ?
C1A C2A C3A 90.9(5) . . ?
C6A C3A C4A 116.5(5) . . ?
C6A C3A C2A 117.3(6) . . ?
C4A C3A C2A 89.0(5) . . ?
C5A C4A C3A 109.6(6) . . ?
C5A C4A C1A 58.6(4) . . ?
C3A C4A C1A 89.3(5) . . ?
C4A C5A C1A 62.9(5) . . ?
C11A C6A C7A 118.7(7) . . ?
C11A C6A C3A 121.3(6) . . ?
C7A C6A C3A 120.0(7) . . ?
C8A C7A C6A 120.1(8) . . ?
C9A C8A C7A 121.4(8) . . ?
C8A C9A C10A 119.7(8) . . ?
C9A C10A C11A 119.3(8) . . ?
C6A C11A C10A 120.8(7) . . ?
O1A C12A O2A 124.3(7) . . ?
O1A C12A C1A 118.4(7) . . ?
O2A C12A C1A 117.3(7) . . ?
 
_refine_diff_density_max    0.185
_refine_diff_density_min   -0.200
_refine_diff_density_rms    0.045



