 
data_XR180
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_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            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                    6.0802(8)
_cell_length_b                    7.0558(8)
_cell_length_c                    22.379(3)
_cell_angle_alpha                 90
_cell_angle_beta                  93.955(4)
_cell_angle_gamma                 90
_cell_volume                      957.8(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     143(2)
_cell_measurement_reflns_used     795
_cell_measurement_theta_min       3.03
_cell_measurement_theta_max       24.45
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_diffrn     1.305          
_exptl_crystal_F_000              400
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.693
_exptl_crystal_size_mid           0.250
_exptl_crystal_size_min           0.082
_exptl_absorpt_coefficient_mu     0.088
_shelx_estimated_absorpt_T_min    0.942
_shelx_estimated_absorpt_T_max    0.993
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.8652  
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details    'face indexing'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       143(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             5491
_diffrn_reflns_av_unetI/netI      0.0570
_diffrn_reflns_av_R_equivalents   0.0464
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          3.028
_diffrn_reflns_theta_max          25.710
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              1830
_reflns_number_gt                 1235
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0354P)²+0.3784P] 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_number_reflns          1830
_refine_ls_number_parameters      168
_refine_ls_number_restraints      15
_refine_ls_R_factor_all           0.0953
_refine_ls_R_factor_gt            0.0575
_refine_ls_wR_factor_ref          0.1246
_refine_ls_wR_factor_gt           0.1093
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_restrained_S_all       1.053
_refine_ls_shift/su_max           0.006
_refine_ls_shift/su_mean          0.001
 
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 0.4240(2) -0.3652(2) 0.05560(7) 0.0353(4) Uani 1 1 d . . . . .
O2 O 0.7455(3) -0.3584(2) 0.01206(7) 0.0356(4) Uani 1 1 d D . . . .
C1 C 0.6904(3) -0.1378(3) 0.08768(9) 0.0267(5) Uani 1 1 d D . . . .
C2A C 0.5693(18) -0.0268(11) 0.1317(5) 0.028(2) Uani 0.550(7) 1 d D . P A 1
H2A1 H 0.6272 -0.0447 0.1737 0.033 Uiso 0.550(7) 1 calc R U P A 1
H2A2 H 0.4076 -0.0455 0.1275 0.033 Uiso 0.550(7) 1 calc R U P A 1
C3A C 0.6461(9) 0.1587(7) 0.1033(2) 0.0286(15) Uani 0.550(7) 1 d D . P A 1
H3A H 0.5191 0.2209 0.0803 0.034 Uiso 0.550(7) 1 calc R U P A 1
C4A C 0.7845(8) 0.0504(8) 0.0609(2) 0.0340(14) Uani 0.550(7) 1 d D . P A 1
H4A H 0.7880 0.0776 0.0172 0.041 Uiso 0.550(7) 1 calc R U P A 1
C5A C 0.9341(17) -0.0828(12) 0.0944(6) 0.0307(19) Uani 0.550(7) 1 d D . P A 1
H5A1 H 0.9952 -0.0431 0.1346 0.037 Uiso 0.550(7) 1 calc R U P A 1
H5A2 H 1.0374 -0.1566 0.0712 0.037 Uiso 0.550(7) 1 calc R U P A 1
C2B C 0.893(2) -0.0213(15) 0.0856(6) 0.032(2) Uani 0.450(7) 1 d D . P A 2
H2B1 H 0.9679 -0.0370 0.0480 0.038 Uiso 0.450(7) 1 calc R U P A 2
H2B2 H 0.9984 -0.0393 0.1209 0.038 Uiso 0.450(7) 1 calc R U P A 2
C3B C 0.7590(10) 0.1646(8) 0.0878(3) 0.0244(17) Uani 0.450(7) 1 d D . P A 2
H3B H 0.7558 0.2307 0.0483 0.029 Uiso 0.450(7) 1 calc R U P A 2
C4B C 0.5469(10) 0.0510(9) 0.0929(3) 0.0300(16) Uani 0.450(7) 1 d D . P A 2
H4B H 0.4060 0.0765 0.0684 0.036 Uiso 0.450(7) 1 calc R U P A 2
C5B C 0.569(3) -0.0856(14) 0.1430(6) 0.026(2) Uani 0.450(7) 1 d D . P A 2
H5B1 H 0.4370 -0.1615 0.1510 0.031 Uiso 0.450(7) 1 calc R U P A 2
H5B2 H 0.6594 -0.0467 0.1793 0.031 Uiso 0.450(7) 1 calc R U P A 2
C6 C 0.7855(4) 0.3104(3) 0.13941(10) 0.0399(6) Uani 1 1 d . . . . .
C7 C 0.6609(4) 0.3775(3) 0.18387(13) 0.0469(7) Uani 1 1 d . . . . .
H7 H 0.5179 0.3267 0.1877 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7387(5) 0.5156(3) 0.22261(11) 0.0459(7) Uani 1 1 d . . . . .
H8 H 0.6491 0.5600 0.2528 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9449(4) 0.5906(3) 0.21821(10) 0.0414(6) Uani 1 1 d . . . . .
H9 H 0.9994 0.6858 0.2453 0.050 Uiso 1 1 calc R U . . .
C10 C 1.0704(4) 0.5263(3) 0.17427(13) 0.0477(7) Uani 1 1 d . . . . .
H10 H 1.2135 0.5772 0.1706 0.057 Uiso 1 1 calc R U . . .
C11 C 0.9903(5) 0.3878(3) 0.13519(11) 0.0498(8) Uani 1 1 d . . . . .
H11 H 1.0792 0.3451 0.1046 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6109(4) -0.2975(3) 0.05098(9) 0.0283(5) Uani 1 1 d . . . . .
H2 H 0.683(4) -0.456(3) -0.0097(11) 0.074(10) 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
O1 C12 1.243(2) . ?
O2 C12 1.308(2) . ?
C1 C12 1.457(3) . ?
C1 C2B 1.484(13) . ?
C1 C2A 1.491(11) . ?
C1 C5B 1.530(13) . ?
C1 C5A 1.529(11) . ?
C1 C4A 1.580(5) . ?
C1 C4B 1.601(6) . ?
C2A C3A 1.541(5) . ?
C3A C4A 1.518(7) . ?
C3A C6 1.556(6) . ?
C4A C5A 1.475(5) . ?
C2B C3B 1.547(9) . ?
C3B C4B 1.529(8) . ?
C3B C6 1.547(7) . ?
C4B C5B 1.478(9) . ?
C6 C11 1.369(3) . ?
C6 C7 1.375(3) . ?
C7 C8 1.367(3) . ?
C8 C9 1.370(3) . ?
C9 C10 1.363(3) . ?
C10 C11 1.378(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
C12 C1 C2B 130.8(5) . . ?
C12 C1 C2A 128.2(4) . . ?
C12 C1 C5B 118.8(6) . . ?
C2B C1 C5B 109.9(8) . . ?
C12 C1 C5A 122.2(5) . . ?
C2A C1 C5A 108.8(7) . . ?
C12 C1 C4A 123.4(3) . . ?
C2A C1 C4A 91.0(3) . . ?
C5A C1 C4A 56.6(2) . . ?
C12 C1 C4B 121.5(3) . . ?
C2B C1 C4B 90.0(4) . . ?
C5B C1 C4B 56.3(3) . . ?
C1 C2A C3A 89.9(5) . . ?
C4A C3A C2A 91.5(5) . . ?
C4A C3A C6 111.4(5) . . ?
C2A C3A C6 122.7(6) . . ?
C5A C4A C3A 110.7(6) . . ?
C5A C4A C1 60.0(5) . . ?
C3A C4A C1 87.4(3) . . ?
C4A C5A C1 63.4(4) . . ?
C1 C2B C3B 91.6(7) . . ?
C4B C3B C2B 90.4(6) . . ?
C4B C3B C6 109.8(5) . . ?
C2B C3B C6 124.1(6) . . ?
C5B C4B C3B 111.4(8) . . ?
C5B C4B C1 59.4(6) . . ?
C3B C4B C1 87.9(3) . . ?
C4B C5B C1 64.3(5) . . ?
C11 C6 C7 117.5(2) . . ?
C11 C6 C3B 105.2(3) . . ?
C7 C6 C3B 137.3(3) . . ?
C11 C6 C3A 134.8(3) . . ?
C7 C6 C3A 107.7(3) . . ?
C8 C7 C6 121.3(2) . . ?
C7 C8 C9 120.5(2) . . ?
C10 C9 C8 118.9(2) . . ?
C9 C10 C11 120.2(2) . . ?
C6 C11 C10 121.5(2) . . ?
O1 C12 O2 123.1(2) . . ?
O1 C12 C1 121.30(19) . . ?
O2 C12 C1 115.52(19) . . ?
 
_refine_diff_density_max    0.162
_refine_diff_density_min   -0.226
_refine_diff_density_rms    0.039



