data_20220524al_0m_a
_audit_creation_date               2023-09-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C15 H12 O2'
_chemical_formula_sum              'C15 H12 O2'
_chemical_formula_weight           224.25
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0148 0.0070 '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' 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     12.6299(9)
_cell_length_b                     12.0299(7)
_cell_length_c                     7.6700(4)
_cell_angle_alpha                  90
_cell_angle_beta                   102.285(4)
_cell_angle_gamma                  90
_cell_volume                       1138.67(12)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7186
_cell_measurement_temperature      150.0
_cell_measurement_theta_max        57.017
_cell_measurement_theta_min        4.465
_shelx_estimated_absorpt_T_max     0.949
_shelx_estimated_absorpt_T_min     0.925
_exptl_absorpt_coefficient_mu      0.443
_exptl_absorpt_correction_T_max    0.7512
_exptl_absorpt_correction_T_min    0.3608
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1530 before and 0.0983 after correction.
The Ratio of minimum to maximum transmission is 0.4803.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear yellowish yellow'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     yellowish
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.308
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               472
_exptl_crystal_size_max            0.18
_exptl_crystal_size_mid            0.14
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0635
_diffrn_reflns_av_unetI/netI       0.0576
_diffrn_reflns_Laue_measured_fraction_full  0.982
_diffrn_reflns_Laue_measured_fraction_max  0.981
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         8
_diffrn_reflns_limit_l_min         -9
_diffrn_reflns_number              9018
_diffrn_reflns_point_group_measured_fraction_full  0.982
_diffrn_reflns_point_group_measured_fraction_max  0.981
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           56.949
_diffrn_reflns_theta_min           4.465
_diffrn_ambient_temperature        150.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.982
_diffrn_measured_fraction_theta_max  0.981
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34138
_diffrn_source                     ?
_diffrn_source_current             2.86
_diffrn_source_power               0.1997996
_diffrn_source_voltage             69.86
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2111
_reflns_number_total               2286
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max           0.393
_refine_diff_density_min           -0.425
_refine_diff_density_rms           0.084
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       158
_refine_ls_number_reflns           2286
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0725
_refine_ls_R_factor_gt             0.0704
_refine_ls_restrained_S_all        1.083
_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)+(0.1306P)²+0.1770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1813
_refine_ls_wR_factor_ref           0.1854
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1A), C9(H9), C4(H4), C5(H5), C15(H15), C3(H3), C11(H11), C14(H14),
  C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     ?
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 0.69360(9) 0.47180(9) 0.58571(16) 0.0412(4) Uani 1 1 d . . . . .
 O2 O 0.41729(9) 0.08859(9) 0.71284(16) 0.0387(3) Uani 1 1 d . . . . .
 C8 C 0.34838(10) 0.27221(12) 0.69919(17) 0.0276(4) Uani 1 1 d . . . . .
 H8 H 0.361217 0.347842 0.674647 0.033 Uiso 1 1 calc R U . . .
 C1 C 0.56234(10) 0.33452(11) 0.62684(16) 0.0258(4) Uani 1 1 d . . . . .
 H1A H 0.515409 0.390706 0.653693 0.031 Uiso 1 1 calc R U . . .
 C9 C 0.25613(10) 0.24487(12) 0.74705(17) 0.0282(4) Uani 1 1 d . . . . .
 H9 H 0.247899 0.168820 0.774819 0.034 Uiso 1 1 calc R U . . .
 C10 C 0.16646(10) 0.31836(12) 0.76160(17) 0.0262(4) Uani 1 1 d . . . . .
 C6 C 0.53272(10) 0.22272(11) 0.63009(16) 0.0247(4) Uani 1 1 d . . . . .
 C7 C 0.43096(10) 0.18822(12) 0.68337(17) 0.0265(4) Uani 1 1 d . . . . .
 C2 C 0.66033(10) 0.36367(12) 0.58440(17) 0.0280(4) Uani 1 1 d . . . . .
 C4 C 0.69745(10) 0.17079(13) 0.54101(18) 0.0311(4) Uani 1 1 d . . . . .
 H4 H 0.743235 0.114966 0.509636 0.037 Uiso 1 1 calc R U . . .
 C5 C 0.60135(11) 0.14067(12) 0.58785(18) 0.0290(4) Uani 1 1 d . . . . .
 H5 H 0.582197 0.064455 0.591220 0.035 Uiso 1 1 calc R U . . .
 C15 C 0.07818(11) 0.27413(13) 0.82058(19) 0.0332(4) Uani 1 1 d . . . . .
 H15 H 0.078949 0.198012 0.853816 0.040 Uiso 1 1 calc R U . . .
 C3 C 0.72755(11) 0.28181(13) 0.53944(18) 0.0306(4) Uani 1 1 d . . . . .
 H3 H 0.793783 0.301723 0.507785 0.037 Uiso 1 1 calc R U . . .
 C11 C 0.16387(11) 0.43060(13) 0.7145(2) 0.0371(4) Uani 1 1 d . . . . .
 H11 H 0.223486 0.462615 0.675266 0.044 Uiso 1 1 calc R U . . .
 C14 C -0.01070(12) 0.33935(15) 0.8315(2) 0.0394(4) Uani 1 1 d . . . . .
 H14 H -0.070244 0.307971 0.871821 0.047 Uiso 1 1 calc R U . . .
 C12 C 0.07501(13) 0.49537(15) 0.7247(3) 0.0480(5) Uani 1 1 d . . . . .
 H12 H 0.073686 0.571453 0.691182 0.058 Uiso 1 1 calc R U . . .
 C13 C -0.01230(12) 0.45026(16) 0.7836(2) 0.0438(4) Uani 1 1 d . . . . .
 H13 H -0.072935 0.495391 0.790883 0.053 Uiso 1 1 calc R U . . .
 H1 H 0.6534(17) 0.5131(19) 0.656(3) 0.057(6) Uiso 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
 O1 C2 1.3663(17) . ?
 O1 H1 0.95(2) . ?
 O2 C7 1.2386(18) . ?
 C8 H8 0.9500 . ?
 C8 C9 1.3351(19) . ?
 C8 C7 1.4755(19) . ?
 C1 H1A 0.9500 . ?
 C1 C6 1.3977(18) . ?
 C1 C2 1.3899(17) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.4596(19) . ?
 C10 C15 1.3949(18) . ?
 C10 C11 1.396(2) . ?
 C6 C7 1.4882(17) . ?
 C6 C5 1.3964(18) . ?
 C2 C3 1.391(2) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.3853(19) . ?
 C4 C3 1.389(2) . ?
 C5 H5 0.9500 . ?
 C15 H15 0.9500 . ?
 C15 C14 1.387(2) . ?
 C3 H3 0.9500 . ?
 C11 H11 0.9500 . ?
 C11 C12 1.382(2) . ?
 C14 H14 0.9500 . ?
 C14 C13 1.383(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.388(2) . ?
 C13 H13 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
 C2 O1 H1 107.5(14) . . ?
 C9 C8 H8 119.1 . . ?
 C9 C8 C7 121.83(13) . . ?
 C7 C8 H8 119.1 . . ?
 C6 C1 H1A 119.9 . . ?
 C2 C1 H1A 119.9 . . ?
 C2 C1 C6 120.13(13) . . ?
 C8 C9 H9 116.3 . . ?
 C8 C9 C10 127.48(13) . . ?
 C10 C9 H9 116.3 . . ?
 C15 C10 C9 118.72(13) . . ?
 C15 C10 C11 118.44(13) . . ?
 C11 C10 C9 122.81(12) . . ?
 C1 C6 C7 121.56(12) . . ?
 C5 C6 C1 119.63(12) . . ?
 C5 C6 C7 118.78(12) . . ?
 O2 C7 C8 121.28(12) . . ?
 O2 C7 C6 118.82(13) . . ?
 C8 C7 C6 119.90(12) . . ?
 O1 C2 C1 121.75(13) . . ?
 O1 C2 C3 118.22(12) . . ?
 C1 C2 C3 120.02(13) . . ?
 C5 C4 H4 119.7 . . ?
 C5 C4 C3 120.67(13) . . ?
 C3 C4 H4 119.7 . . ?
 C6 C5 H5 120.1 . . ?
 C4 C5 C6 119.78(13) . . ?
 C4 C5 H5 120.1 . . ?
 C10 C15 H15 119.4 . . ?
 C14 C15 C10 121.14(14) . . ?
 C14 C15 H15 119.4 . . ?
 C2 C3 H3 120.1 . . ?
 C4 C3 C2 119.73(12) . . ?
 C4 C3 H3 120.1 . . ?
 C10 C11 H11 119.8 . . ?
 C12 C11 C10 120.34(14) . . ?
 C12 C11 H11 119.8 . . ?
 C15 C14 H14 120.1 . . ?
 C13 C14 C15 119.74(14) . . ?
 C13 C14 H14 120.1 . . ?
 C11 C12 H12 119.7 . . ?
 C11 C12 C13 120.60(16) . . ?
 C13 C12 H12 119.7 . . ?
 C14 C13 C12 119.73(14) . . ?
 C14 C13 H13 120.1 . . ?
 C12 C13 H13 120.1 . . ?

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
 O1 C2 C3 C4 178.44(12) . . . . ?
 C8 C9 C10 C15 -177.64(14) . . . . ?
 C8 C9 C10 C11 4.1(2) . . . . ?
 C1 C6 C7 O2 -168.06(13) . . . . ?
 C1 C6 C7 C8 12.28(19) . . . . ?
 C1 C6 C5 C4 -0.8(2) . . . . ?
 C1 C2 C3 C4 -1.4(2) . . . . ?
 C9 C8 C7 O2 0.5(2) . . . . ?
 C9 C8 C7 C6 -179.82(12) . . . . ?
 C9 C10 C15 C14 -177.94(13) . . . . ?
 C9 C10 C11 C12 177.58(15) . . . . ?
 C10 C15 C14 C13 -0.1(2) . . . . ?
 C10 C11 C12 C13 0.7(3) . . . . ?
 C6 C1 C2 O1 -177.78(12) . . . . ?
 C6 C1 C2 C3 2.1(2) . . . . ?
 C7 C8 C9 C10 -177.63(12) . . . . ?
 C7 C6 C5 C4 -178.84(11) . . . . ?
 C2 C1 C6 C7 177.03(11) . . . . ?
 C2 C1 C6 C5 -0.96(19) . . . . ?
 C5 C6 C7 O2 9.96(19) . . . . ?
 C5 C6 C7 C8 -169.70(11) . . . . ?
 C5 C4 C3 C2 -0.3(2) . . . . ?
 C15 C10 C11 C12 -0.7(2) . . . . ?
 C15 C14 C13 C12 0.1(3) . . . . ?
 C3 C4 C5 C6 1.4(2) . . . . ?
 C11 C10 C15 C14 0.4(2) . . . . ?
 C11 C12 C13 C14 -0.4(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
