  
data_2c
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C15 H16 O2' 
_chemical_formula_sum
 'C15 H16 O2' 
_chemical_formula_weight          228.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0492   0.0322
 '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/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    6.4612(2)
_cell_length_b                    11.7915(4)
_cell_length_c                    15.9166(5)
_cell_angle_alpha                 90
_cell_angle_beta                  100.808(2)
_cell_angle_gamma                 90
_cell_volume                      1191.13(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used      4772
_cell_measurement_theta_min        4.70
_cell_measurement_theta_max       72.04
 
_exptl_crystal_description        'prism'
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.273          
_exptl_crystal_F_000              488
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.661
_shelx_estimated_absorpt_T_min    0.826
_shelx_estimated_absorpt_T_max    0.879
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6160
_exptl_absorpt_correction_T_max   0.7535
_exptl_absorpt_process_details    'Bruker SADABS'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'micro focus'
_diffrn_measurement_device_type   'Bruker D8 Venture'
_diffrn_measurement_method        'phi / omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6421
_diffrn_reflns_av_unetI/netI      0.0313
_diffrn_reflns_av_R_equivalents   0.0335
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          4.697
_diffrn_reflns_theta_max          72.062
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.967
_diffrn_measured_fraction_theta_full  0.985
_diffrn_reflns_Laue_measured_fraction_max    0.967
_diffrn_reflns_Laue_measured_fraction_full   0.985
_diffrn_reflns_point_group_measured_fraction_max   0.967
_diffrn_reflns_point_group_measured_fraction_full  0.985
_reflns_number_total              2261
_reflns_number_gt                 1985
_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 APEX 3'
_computing_cell_refinement    'Bruker APEX 3'
_computing_data_reduction     'Bruker APEX 3'
_computing_structure_solution     'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement 
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics       'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material   'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0370P)²+0.5422P] 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          2261
_refine_ls_number_parameters      155
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0458
_refine_ls_R_factor_gt            0.0381
_refine_ls_wR_factor_ref          0.0993
_refine_ls_wR_factor_gt           0.0949
_refine_ls_goodness_of_fit_ref    1.115
_refine_ls_restrained_S_all       1.115
_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
O1 O 0.99699(17) 0.05184(9) 0.20033(7) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.8699(2) 0.10811(11) 0.23029(9) 0.0185(3) Uani 1 1 d . . . . .
O2 O 1.11211(14) 0.19349(8) 0.35179(6) 0.0204(2) Uani 1 1 d . . . . .
C2 C 0.9153(2) 0.18597(11) 0.30338(8) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.9519(2) 0.31457(12) 0.44882(9) 0.0221(3) Uani 1 1 d . . . . .
H4A H 0.9783 0.3829 0.4854 0.026 Uiso 1 1 calc R U . . .
H4AB H 0.9349 0.2491 0.4859 0.026 Uiso 1 1 calc R U . . .
C3 C 1.1383(2) 0.29405(12) 0.40511(10) 0.0238(3) Uani 1 1 d . . . . .
H3A H 1.1567 0.3607 0.3694 0.029 Uiso 1 1 calc R U . . .
H3AB H 1.2677 0.2860 0.4492 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7489(2) 0.33096(12) 0.38211(8) 0.0188(3) Uani 1 1 d . . . . .
H5A H 0.6243 0.3216 0.4094 0.023 Uiso 1 1 calc R U . . .
H5AB H 0.7454 0.4083 0.3576 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7441(2) 0.24473(11) 0.31304(8) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.5537(2) 0.21310(11) 0.24690(8) 0.0150(3) Uani 1 1 d . . . . .
H7 H 0.4403 0.1859 0.2770 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6325(2) 0.11055(11) 0.19892(8) 0.0175(3) Uani 1 1 d . . . . .
H8 H 0.5741 0.0402 0.2208 0.021 Uiso 1 1 calc R U . . .
C9 C 0.5694(2) 0.10838(12) 0.10175(9) 0.0251(3) Uani 1 1 d . . . . .
H9A H 0.6203 0.1774 0.0779 0.038 Uiso 1 1 calc R U . . .
H9B H 0.4156 0.1046 0.0855 0.038 Uiso 1 1 calc R U . . .
H9C H 0.6318 0.0418 0.0793 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4692(2) 0.31308(11) 0.19002(8) 0.0144(3) Uani 1 1 d . . . . .
C11 C 0.2528(2) 0.32516(12) 0.16108(8) 0.0179(3) Uani 1 1 d . . . . .
H11 H 0.1584 0.2715 0.1776 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1742(2) 0.41537(12) 0.10815(9) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.0266 0.4232 0.0891 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3107(2) 0.49373(12) 0.08317(8) 0.0201(3) Uani 1 1 d . . . . .
H13 H 0.2570 0.5545 0.0463 0.024 Uiso 1 1 calc R U . . .
C14 C 0.5265(2) 0.48309(12) 0.11223(8) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.6204 0.5369 0.0956 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6047(2) 0.39357(11) 0.16570(8) 0.0165(3) Uani 1 1 d . . . . .
H15 H 0.7522 0.3872 0.1859 0.020 Uiso 1 1 calc R U . . .
 
 
_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
O1 C1 1.2203(17) . ?
C1 C2 1.4678(19) . ?
C1 C8 1.5218(18) . ?
O2 C2 1.3605(16) . ?
O2 C3 1.4495(17) . ?
C2 C6 1.3385(18) . ?
C4 C3 1.519(2) . ?
C4 C5 1.5372(18) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C5 C6 1.4935(18) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.5085(17) . ?
C7 C10 1.5237(17) . ?
C7 C8 1.5653(18) . ?
C7 H7 1.0000 . ?
C8 C9 1.5240(18) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.3941(18) . ?
C10 C11 1.3950(18) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3902(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
 
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 126.91(13) . . ?
O1 C1 C8 126.37(13) . . ?
C2 C1 C8 106.72(11) . . ?
C2 O2 C3 112.27(10) . . ?
C6 C2 O2 127.31(12) . . ?
C6 C2 C1 111.60(12) . . ?
O2 C2 C1 121.09(11) . . ?
C3 C4 C5 110.54(11) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.1 . . ?
O2 C3 C4 112.51(11) . . ?
O2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
O2 C3 H3AB 109.1 . . ?
C4 C3 H3AB 109.1 . . ?
H3A C3 H3AB 107.8 . . ?
C6 C5 C4 108.66(11) . . ?
C6 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C6 C5 H5AB 110.0 . . ?
C4 C5 H5AB 110.0 . . ?
H5A C5 H5AB 108.3 . . ?
C2 C6 C5 122.24(12) . . ?
C2 C6 C7 112.05(12) . . ?
C5 C6 C7 125.71(11) . . ?
C6 C7 C10 112.19(10) . . ?
C6 C7 C8 103.54(10) . . ?
C10 C7 C8 114.89(10) . . ?
C6 C7 H7 108.7 . . ?
C10 C7 H7 108.7 . . ?
C8 C7 H7 108.7 . . ?
C1 C8 C9 113.19(11) . . ?
C1 C8 C7 104.75(10) . . ?
C9 C8 C7 117.29(11) . . ?
C1 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.77(12) . . ?
C15 C10 C7 121.21(11) . . ?
C11 C10 C7 120.02(11) . . ?
C12 C11 C10 120.47(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.23(12) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.79(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.94(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.79(12) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C3 O2 C2 C6 -14.63(18) . . . . ?
C3 O2 C2 C1 164.62(12) . . . . ?
O1 C1 C2 C6 172.28(13) . . . . ?
C8 C1 C2 C6 -7.91(15) . . . . ?
O1 C1 C2 O2 -7.1(2) . . . . ?
C8 C1 C2 O2 172.74(11) . . . . ?
C2 O2 C3 C4 44.23(15) . . . . ?
C5 C4 C3 O2 -60.45(16) . . . . ?
C3 C4 C5 C6 42.99(15) . . . . ?
O2 C2 C6 C5 0.2(2) . . . . ?
C1 C2 C6 C5 -179.14(11) . . . . ?
O2 C2 C6 C7 180.00(12) . . . . ?
C1 C2 C6 C7 0.69(15) . . . . ?
C4 C5 C6 C2 -15.25(18) . . . . ?
C4 C5 C6 C7 164.94(12) . . . . ?
C2 C6 C7 C10 -117.93(12) . . . . ?
C5 C6 C7 C10 61.89(16) . . . . ?
C2 C6 C7 C8 6.52(14) . . . . ?
C5 C6 C7 C8 -173.66(12) . . . . ?
O1 C1 C8 C9 -39.89(19) . . . . ?
C2 C1 C8 C9 140.30(11) . . . . ?
O1 C1 C8 C7 -168.84(13) . . . . ?
C2 C1 C8 C7 11.34(13) . . . . ?
C6 C7 C8 C1 -10.66(12) . . . . ?
C10 C7 C8 C1 112.03(12) . . . . ?
C6 C7 C8 C9 -137.11(12) . . . . ?
C10 C7 C8 C9 -14.42(16) . . . . ?
C6 C7 C10 C15 35.76(16) . . . . ?
C8 C7 C10 C15 -82.14(15) . . . . ?
C6 C7 C10 C11 -144.43(12) . . . . ?
C8 C7 C10 C11 97.67(14) . . . . ?
C15 C10 C11 C12 0.67(19) . . . . ?
C7 C10 C11 C12 -179.14(12) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C10 0.71(19) . . . . ?
C11 C10 C15 C14 -1.26(19) . . . . ?
C7 C10 C15 C14 178.55(12) . . . . ?
 
_refine_diff_density_max    0.211
_refine_diff_density_min   -0.234
_refine_diff_density_rms    0.053



