# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_120K
_database_code_depnum_ccdc_archive 'CCDC 1855848'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6861(4)
_cell_length_b                   7.4078(5)
_cell_length_c                   28.140(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1185.30(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.66

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12587
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.000
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2935
_reflns_number_gt                2386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0345P)²+0.2437P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2935
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.9004(4) 0.3664(3) 0.06843(8) 0.0338(6) Uani 1 1 d . . . . .
H1A H 0.968305 0.361318 0.036446 0.051 Uiso 1 1 calc R U . . .
H1B H 0.889873 0.244053 0.081503 0.051 Uiso 1 1 calc R U . . .
H1C H 1.000625 0.440637 0.088940 0.051 Uiso 1 1 calc R U . . .
C2 C 0.6565(4) 0.4487(3) 0.06594(7) 0.0194(5) Uani 1 1 d . . . . .
H2 H 0.556252 0.371441 0.044998 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5481(4) 0.4568(3) 0.11332(7) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.4628(4) 0.4537(3) 0.15201(7) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.3568(4) 0.4432(3) 0.19861(7) 0.0160(4) Uani 1 1 d . . . . .
C6 C 0.1392(4) 0.3582(3) 0.20448(7) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.059114 0.310433 0.177642 0.022 Uiso 1 1 calc R U . . .
C7 C 0.0399(4) 0.3433(3) 0.24918(7) 0.0170(4) Uani 1 1 d . . . . .
H7 H -0.107891 0.285103 0.252828 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1548(4) 0.4131(2) 0.28897(7) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.3715(4) 0.4982(3) 0.28316(7) 0.0170(4) Uani 1 1 d . . . . .
H9 H 0.451469 0.545969 0.310006 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4708(4) 0.5135(3) 0.23843(7) 0.0170(4) Uani 1 1 d . . . . .
H10 H 0.618078 0.572397 0.234803 0.020 Uiso 1 1 calc R U . . .
C11 C 0.0450(4) 0.3969(3) 0.33482(7) 0.0186(4) Uani 1 1 d . . . . .
C12 C -0.0559(4) 0.3806(3) 0.37179(7) 0.0188(4) Uani 1 1 d . . . . .
C13 C -0.1786(4) 0.3585(3) 0.41753(7) 0.0181(4) Uani 1 1 d . . . . .
H13 H -0.246732 0.234170 0.419013 0.022 Uiso 1 1 calc R U . . .
C14 C -0.3738(4) 0.4941(3) 0.42422(7) 0.0239(5) Uani 1 1 d . . . . .
H14A H -0.444849 0.477673 0.455647 0.036 Uiso 1 1 calc R U . . .
H14B H -0.493610 0.476197 0.399638 0.036 Uiso 1 1 calc R U . . .
H14C H -0.309609 0.616520 0.421713 0.036 Uiso 1 1 calc R U . . .
O1 O 0.6663(3) 0.62724(19) 0.04600(5) 0.0199(3) Uani 1 1 d . . . . .
O2 O -0.0140(3) 0.3801(2) 0.45601(5) 0.0222(4) Uani 1 1 d . . . . .
H1 H 0.629(5) 0.622(4) 0.0180(10) 0.043(8) Uiso 1 1 d . . . . .
H2A H 0.101(6) 0.298(4) 0.4513(10) 0.050(9) 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
C1 C2 1.516(3) . ?
C2 O1 1.438(2) . ?
C2 C3 1.470(3) . ?
C3 C4 1.192(3) . ?
C4 C5 1.445(3) . ?
C5 C10 1.395(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.394(3) . ?
C8 C11 1.438(3) . ?
C9 C10 1.384(3) . ?
C11 C12 1.194(3) . ?
C12 C13 1.473(3) . ?
C13 O2 1.440(2) . ?
C13 C14 1.509(3) . ?

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 C2 C3 109.42(16) . . ?
O1 C2 C1 110.65(18) . . ?
C3 C2 C1 110.98(17) . . ?
C4 C3 C2 176.5(2) . . ?
C3 C4 C5 177.9(2) . . ?
C10 C5 C6 118.96(17) . . ?
C10 C5 C4 120.99(18) . . ?
C6 C5 C4 120.03(18) . . ?
C7 C6 C5 120.30(18) . . ?
C6 C7 C8 120.59(19) . . ?
C9 C8 C7 119.16(17) . . ?
C9 C8 C11 121.80(17) . . ?
C7 C8 C11 119.04(18) . . ?
C10 C9 C8 120.28(18) . . ?
C9 C10 C5 120.70(19) . . ?
C12 C11 C8 176.8(2) . . ?
C11 C12 C13 179.3(2) . . ?
O2 C13 C12 109.70(16) . . ?
O2 C13 C14 108.07(16) . . ?
C12 C13 C14 112.52(17) . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_310K
_database_code_depnum_ccdc_archive 'CCDC 1855855'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7075(7)
_cell_length_b                   7.6016(7)
_cell_length_c                   28.125(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1220.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    310(2)
_cell_measurement_reflns_used    2432
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.50

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      310(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13440
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_full        25.000
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3040
_reflns_number_gt                1532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0413P)²+0.0818P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3040
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1480
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.8843(7) 0.3627(5) 0.06578(13) 0.0930(14) Uani 1 1 d . . . . .
H1A H 0.949532 0.360533 0.034330 0.140 Uiso 1 1 calc R U . . .
H1B H 0.869106 0.244595 0.077442 0.140 Uiso 1 1 calc R U . . .
H1C H 0.985657 0.428333 0.086459 0.140 Uiso 1 1 calc R U . . .
C2 C 0.6462(6) 0.4488(4) 0.06440(10) 0.0520(8) Uani 1 1 d . . . . .
H2 H 0.544290 0.378831 0.043691 0.062 Uiso 1 1 calc R U . . .
C3 C 0.5404(5) 0.4552(4) 0.11177(11) 0.0505(8) Uani 1 1 d . . . . .
C4 C 0.4579(5) 0.4514(4) 0.15044(11) 0.0507(8) Uani 1 1 d . . . . .
C5 C 0.3548(5) 0.4412(4) 0.19721(9) 0.0427(7) Uani 1 1 d . . . . .
C6 C 0.1422(6) 0.3572(4) 0.20382(10) 0.0499(8) Uani 1 1 d . . . . .
H6 H 0.063310 0.310181 0.177834 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0468(5) 0.3429(4) 0.24846(10) 0.0465(8) Uani 1 1 d . . . . .
H7 H -0.095631 0.285362 0.252433 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1603(5) 0.4131(3) 0.28770(10) 0.0404(7) Uani 1 1 d . . . . .
C9 C 0.3711(5) 0.4975(4) 0.28101(10) 0.0490(8) Uani 1 1 d . . . . .
H9 H 0.449108 0.545474 0.306991 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4681(5) 0.5117(4) 0.23633(10) 0.0481(8) Uani 1 1 d . . . . .
H10 H 0.610673 0.569146 0.232417 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0534(5) 0.3971(4) 0.33367(11) 0.0498(8) Uani 1 1 d . . . . .
C12 C -0.0445(6) 0.3803(4) 0.37066(11) 0.0515(8) Uani 1 1 d . . . . .
C13 C -0.1689(5) 0.3580(4) 0.41612(10) 0.0503(8) Uani 1 1 d . . . . .
H13 H -0.238017 0.240030 0.416938 0.060 Uiso 1 1 calc R U . . .
C14 C -0.3602(5) 0.4906(5) 0.42282(11) 0.0683(10) Uani 1 1 d . . . . .
H14A H -0.436893 0.470138 0.452692 0.102 Uiso 1 1 calc R U . . .
H14B H -0.471887 0.479902 0.397469 0.102 Uiso 1 1 calc R U . . .
H14C H -0.294360 0.606842 0.422607 0.102 Uiso 1 1 calc R U . . .
O1 O 0.6614(4) 0.6221(3) 0.04534(8) 0.0547(6) Uani 1 1 d . . . . .
O2 O -0.0076(4) 0.3742(3) 0.45477(7) 0.0626(7) Uani 1 1 d . . . . .
H2A H 0.106(8) 0.294(5) 0.4486(13) 0.111(16) Uiso 1 1 d . . . . .
H1 H 0.615(7) 0.623(5) 0.0164(14) 0.109(16) 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
C1 C2 1.509(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.425(3) . ?
C2 C3 1.463(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.186(4) . ?
C4 C5 1.443(4) . ?
C5 C10 1.384(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 C11 1.435(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.188(4) . ?
C12 C13 1.472(4) . ?
C13 O2 1.430(3) . ?
C13 C14 1.498(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.86(4) . ?
O2 H2A 0.90(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.7(2) . . ?
O1 C2 C1 110.8(3) . . ?
C3 C2 C1 111.3(3) . . ?
O1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C4 C3 C2 176.5(3) . . ?
C3 C4 C5 178.2(3) . . ?
C10 C5 C6 118.8(3) . . ?
C10 C5 C4 120.9(3) . . ?
C6 C5 C4 120.3(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 C11 122.3(3) . . ?
C7 C8 C11 119.1(3) . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C8 176.8(3) . . ?
C11 C12 C13 179.1(3) . . ?
O2 C13 C12 109.9(2) . . ?
O2 C13 C14 108.4(2) . . ?
C12 C13 C14 112.5(3) . . ?
O2 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 110(3) . . ?
C13 O2 H2A 105(2) . . ?

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_300K
_database_code_depnum_ccdc_archive 'CCDC 1855854'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7073(6)
_cell_length_b                   7.5909(7)
_cell_length_c                   28.133(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1218.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2484
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.61

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13454
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3051
_reflns_number_gt                1605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.995
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0449P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3051
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.8852(6) 0.3631(5) 0.06591(12) 0.0904(12) Uani 1 1 d . . . . .
H1A H 0.949320 0.359016 0.034380 0.136 Uiso 1 1 calc R U . . .
H1B H 0.870666 0.245569 0.078124 0.136 Uiso 1 1 calc R U . . .
H1C H 0.987321 0.430175 0.086120 0.136 Uiso 1 1 calc R U . . .
C2 C 0.6474(5) 0.4489(3) 0.06451(9) 0.0500(8) Uani 1 1 d . . . . .
H2 H 0.545864 0.378549 0.043816 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5408(5) 0.4553(3) 0.11195(10) 0.0491(8) Uani 1 1 d . . . . .
C4 C 0.4577(5) 0.4516(3) 0.15059(10) 0.0487(8) Uani 1 1 d . . . . .
C5 C 0.3552(5) 0.4416(3) 0.19728(9) 0.0410(7) Uani 1 1 d . . . . .
C6 C 0.1422(5) 0.3574(3) 0.20389(9) 0.0489(7) Uani 1 1 d . . . . .
H6 H 0.063323 0.310355 0.177910 0.059 Uiso 1 1 calc R U . . .
C7 C 0.0464(5) 0.3430(3) 0.24870(9) 0.0449(7) Uani 1 1 d . . . . .
H7 H -0.096019 0.285426 0.252704 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1598(5) 0.4132(3) 0.28768(9) 0.0393(6) Uani 1 1 d . . . . .
C9 C 0.3715(5) 0.4978(3) 0.28117(9) 0.0469(7) Uani 1 1 d . . . . .
H9 H 0.449591 0.545453 0.307178 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4681(5) 0.5121(3) 0.23647(9) 0.0457(7) Uani 1 1 d . . . . .
H10 H 0.610546 0.569741 0.232567 0.055 Uiso 1 1 calc R U . . .
C11 C 0.0529(5) 0.3973(4) 0.33368(10) 0.0476(7) Uani 1 1 d . . . . .
C12 C -0.0448(5) 0.3804(3) 0.37069(10) 0.0489(8) Uani 1 1 d . . . . .
C13 C -0.1692(5) 0.3581(3) 0.41605(9) 0.0489(7) Uani 1 1 d . . . . .
H13 H -0.238088 0.239857 0.416859 0.059 Uiso 1 1 calc R U . . .
C14 C -0.3610(5) 0.4907(4) 0.42292(10) 0.0652(9) Uani 1 1 d . . . . .
H14A H -0.436292 0.470560 0.452940 0.098 Uiso 1 1 calc R U . . .
H14B H -0.473730 0.479169 0.397786 0.098 Uiso 1 1 calc R U . . .
H14C H -0.295671 0.607214 0.422416 0.098 Uiso 1 1 calc R U . . .
O1 O 0.6615(4) 0.6222(2) 0.04541(7) 0.0523(6) Uani 1 1 d . . . . .
O2 O -0.0079(4) 0.3743(3) 0.45479(7) 0.0592(6) Uani 1 1 d . . . . .
H2A H 0.103(6) 0.291(4) 0.4484(12) 0.102(14) Uiso 1 1 d . . . . .
H1 H 0.614(6) 0.624(4) 0.0165(12) 0.101(14) 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
C1 C2 1.506(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.423(3) . ?
C2 C3 1.468(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.187(3) . ?
C4 C5 1.440(4) . ?
C5 C10 1.385(3) . ?
C5 C6 1.386(4) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 C11 1.436(4) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.188(3) . ?
C12 C13 1.470(4) . ?
C13 O2 1.432(3) . ?
C13 C14 1.499(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.86(4) . ?
O2 H2A 0.91(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.6(2) . . ?
O1 C2 C1 111.0(2) . . ?
C3 C2 C1 111.4(2) . . ?
O1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C4 C3 C2 176.6(3) . . ?
C3 C4 C5 178.3(3) . . ?
C10 C5 C6 118.6(2) . . ?
C10 C5 C4 121.1(3) . . ?
C6 C5 C4 120.2(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 C11 119.0(2) . . ?
C9 C8 C11 122.1(2) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C8 176.8(3) . . ?
C11 C12 C13 179.0(3) . . ?
O2 C13 C12 109.9(2) . . ?
O2 C13 C14 108.3(2) . . ?
C12 C13 C14 112.8(2) . . ?
O2 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 111(2) . . ?
C13 O2 H2A 104(2) . . ?

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_100K
_database_code_depnum_ccdc_archive 'CCDC 1855861'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8843(4)
_cell_length_b                   7.2086(5)
_cell_length_c                   32.936(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1397.04(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7316
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.18

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8232
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         28.249
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3311
_reflns_number_gt                2777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.947

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0578P)²+0.1892P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.3550(2) 0.6361(2) 0.95936(4) 0.0167(3) Uani 1 1 d . . . . .
O2 O 0.9925(2) 0.3830(2) 0.53569(4) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.1270(4) 0.3732(4) 0.93796(6) 0.0265(5) Uani 1 1 d . . . . .
H1A H 0.059817 0.364505 0.965113 0.040 Uiso 1 1 calc R U . . .
H1B H 0.136640 0.249086 0.925941 0.040 Uiso 1 1 calc R U . . .
H1C H 0.031949 0.452628 0.920793 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3641(3) 0.4561(3) 0.94109(6) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.459047 0.373536 0.958631 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4716(3) 0.4688(3) 0.90079(6) 0.0162(4) Uani 1 1 d . . . . .
C4 C 0.5542(3) 0.4658(3) 0.86760(6) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.6576(3) 0.4491(3) 0.82815(5) 0.0136(4) Uani 1 1 d . . . . .
C6 C 0.5448(3) 0.5023(3) 0.79356(5) 0.0127(4) Uani 1 1 d . . . . .
H6 H 0.400627 0.560764 0.795727 0.015 Uiso 1 1 calc R U . . .
C7 C 0.6405(3) 0.4712(3) 0.75468(5) 0.0109(4) Uani 1 1 d . . . . .
C8 C 0.5246(3) 0.5183(3) 0.71824(5) 0.0124(4) Uani 1 1 d . . . . .
H8 H 0.377795 0.572799 0.719670 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6213(3) 0.4864(3) 0.68128(6) 0.0139(4) Uani 1 1 d . . . . .
H9 H 0.541035 0.518834 0.657277 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8408(3) 0.4052(3) 0.67825(5) 0.0127(4) Uani 1 1 d . . . . .
C11 C 0.9539(3) 0.3545(3) 0.71306(5) 0.0124(4) Uani 1 1 d . . . . .
H11 H 1.098481 0.296568 0.711056 0.015 Uiso 1 1 calc R U . . .
C12 C 0.8584(3) 0.3872(3) 0.75176(5) 0.0107(4) Uani 1 1 d . . . . .
C13 C 0.9742(3) 0.3383(3) 0.78799(5) 0.0130(4) Uani 1 1 d . . . . .
H13 H 1.121321 0.284490 0.786434 0.016 Uiso 1 1 calc R U . . .
C14 C 0.8769(3) 0.3674(3) 0.82502(5) 0.0143(4) Uani 1 1 d . . . . .
H14 H 0.956414 0.332834 0.848956 0.017 Uiso 1 1 calc R U . . .
C15 C 0.9469(3) 0.3827(3) 0.63935(5) 0.0150(4) Uani 1 1 d . . . . .
C16 C 1.0411(3) 0.3700(3) 0.60745(6) 0.0163(4) Uani 1 1 d . . . . .
C17 C 1.1554(3) 0.3559(3) 0.56771(5) 0.0150(4) Uani 1 1 d . . . . .
H17 H 1.223518 0.229427 0.564980 0.018 Uiso 1 1 calc R U . . .
C18 C 1.3408(3) 0.4996(3) 0.56281(6) 0.0206(5) Uani 1 1 d . . . . .
H18A H 1.404812 0.491237 0.535403 0.031 Uiso 1 1 calc R U . . .
H18B H 1.460775 0.476824 0.582848 0.031 Uiso 1 1 calc R U . . .
H18C H 1.277011 0.623643 0.567023 0.031 Uiso 1 1 calc R U . . .
H2A H 0.874(5) 0.302(4) 0.5389(8) 0.039(8) Uiso 1 1 d . . . . .
H1 H 0.399(5) 0.629(4) 0.9823(9) 0.045(9) 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 1.431(3) . ?
O1 H1 0.80(3) . ?
O2 C17 1.438(2) . ?
O2 H2A 0.92(3) . ?
C1 C2 1.521(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.473(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.197(3) . ?
C4 C5 1.440(3) . ?
C5 C6 1.373(3) . ?
C5 C14 1.422(3) . ?
C6 C7 1.417(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.421(2) . ?
C7 C8 1.421(2) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(3) . ?
C10 C15 1.434(3) . ?
C11 C12 1.413(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.419(2) . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.192(3) . ?
C16 C17 1.475(3) . ?
C17 C18 1.513(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 109(2) . . ?
C17 O2 H2A 109.6(17) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.78(17) . . ?
O1 C2 C1 110.52(17) . . ?
C3 C2 C1 110.91(16) . . ?
O1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C4 C3 C2 175.1(2) . . ?
C3 C4 C5 176.1(2) . . ?
C6 C5 C14 119.61(17) . . ?
C6 C5 C4 121.40(17) . . ?
C14 C5 C4 118.92(17) . . ?
C5 C6 C7 120.91(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C12 119.14(16) . . ?
C6 C7 C8 122.33(17) . . ?
C12 C7 C8 118.53(16) . . ?
C9 C8 C7 120.89(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.75(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.38(17) . . ?
C11 C10 C15 120.25(17) . . ?
C9 C10 C15 120.33(17) . . ?
C10 C11 C12 121.01(17) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 121.75(16) . . ?
C11 C12 C7 119.40(16) . . ?
C13 C12 C7 118.85(16) . . ?
C14 C13 C12 120.82(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C5 120.63(17) . . ?
C13 C14 H14 119.7 . . ?
C5 C14 H14 119.7 . . ?
C16 C15 C10 177.2(2) . . ?
C15 C16 C17 179.3(2) . . ?
O2 C17 C16 109.71(15) . . ?
O2 C17 C18 108.02(16) . . ?
C16 C17 C18 112.10(17) . . ?
O2 C17 H17 109.0 . . ?
C16 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_400K
_database_code_depnum_ccdc_archive 'CCDC 1855867'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9264(11)
_cell_length_b                   7.4922(18)
_cell_length_c                   32.946(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1462.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    400(2)
_cell_measurement_reflns_used    5359
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.45

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      400(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8806
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3599
_reflns_number_gt                1960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.986

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0483P)²+0.1171P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.3676(4) 0.6256(3) 0.95997(6) 0.0720(6) Uani 1 1 d . . . . .
O2 O 0.9792(4) 0.3714(4) 0.53732(6) 0.0838(7) Uani 1 1 d . . . . .
C1 C 0.1588(7) 0.3632(6) 0.94117(12) 0.1230(16) Uani 1 1 d . . . . .
H1A H 0.097452 0.354439 0.968057 0.184 Uiso 1 1 calc R U . . .
H1B H 0.175121 0.245773 0.929870 0.184 Uiso 1 1 calc R U . . .
H1C H 0.059072 0.432277 0.924432 0.184 Uiso 1 1 calc R U . . .
C2 C 0.3865(6) 0.4528(4) 0.94296(8) 0.0713(9) Uani 1 1 d . . . . .
H2 H 0.485414 0.381391 0.960407 0.086 Uiso 1 1 calc R U . . .
C3 C 0.4883(5) 0.4625(4) 0.90250(8) 0.0682(8) Uani 1 1 d . . . . .
C4 C 0.5653(5) 0.4596(4) 0.86956(8) 0.0650(8) Uani 1 1 d . . . . .
C5 C 0.6648(4) 0.4436(4) 0.82966(7) 0.0553(7) Uani 1 1 d . . . . .
C6 C 0.5519(4) 0.4968(4) 0.79579(7) 0.0522(7) Uani 1 1 d . . . . .
H6 H 0.412716 0.552925 0.798497 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6417(4) 0.4685(3) 0.75661(6) 0.0448(6) Uani 1 1 d . . . . .
C8 C 0.5252(4) 0.5163(4) 0.72089(7) 0.0539(7) Uani 1 1 d . . . . .
H8 H 0.383739 0.569366 0.722846 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6159(5) 0.4863(4) 0.68388(7) 0.0604(7) Uani 1 1 d . . . . .
H9 H 0.535872 0.518638 0.660740 0.072 Uiso 1 1 calc R U . . .
C10 C 0.8294(5) 0.4068(4) 0.67989(7) 0.0528(7) Uani 1 1 d . . . . .
C11 C 0.9440(4) 0.3567(3) 0.71401(7) 0.0506(7) Uani 1 1 d . . . . .
H11 H 1.083797 0.301393 0.711404 0.061 Uiso 1 1 calc R U . . .
C12 C 0.8552(4) 0.3869(3) 0.75297(6) 0.0442(6) Uani 1 1 d . . . . .
C13 C 0.9711(4) 0.3383(4) 0.78841(7) 0.0546(7) Uani 1 1 d . . . . .
H13 H 1.113737 0.287242 0.786388 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8785(5) 0.3646(4) 0.82554(7) 0.0610(8) Uani 1 1 d . . . . .
H14 H 0.957487 0.329782 0.848616 0.073 Uiso 1 1 calc R U . . .
C15 C 0.9305(5) 0.3839(4) 0.64059(8) 0.0639(8) Uani 1 1 d . . . . .
C16 C 1.0201(5) 0.3690(4) 0.60866(8) 0.0673(8) Uani 1 1 d . . . . .
C17 C 1.1368(5) 0.3528(4) 0.56979(8) 0.0675(8) Uani 1 1 d . . . . .
H17 H 1.206432 0.234347 0.568150 0.081 Uiso 1 1 calc R U . . .
C18 C 1.3158(5) 0.4914(5) 0.56444(9) 0.0933(11) Uani 1 1 d . . . . .
H18A H 1.380481 0.480766 0.537835 0.140 Uiso 1 1 calc R U . . .
H18B H 1.431337 0.474454 0.584508 0.140 Uiso 1 1 calc R U . . .
H18C H 1.250657 0.607866 0.567556 0.140 Uiso 1 1 calc R U . . .
H2A H 0.860(8) 0.287(6) 0.5407(14) 0.16(2) Uiso 1 1 d . . . . .
H1 H 0.416(8) 0.618(6) 0.9859(13) 0.149(17) 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 1.415(4) . ?
O2 C17 1.427(3) . ?
C1 C2 1.508(5) . ?
C2 C3 1.465(4) . ?
C3 C4 1.178(3) . ?
C4 C5 1.445(3) . ?
C5 C6 1.361(3) . ?
C5 C14 1.405(4) . ?
C6 C7 1.412(3) . ?
C7 C12 1.410(3) . ?
C7 C8 1.410(3) . ?
C8 C9 1.352(3) . ?
C9 C10 1.405(4) . ?
C10 C11 1.366(3) . ?
C10 C15 1.437(4) . ?
C11 C12 1.406(3) . ?
C12 C13 1.403(3) . ?
C13 C14 1.355(3) . ?
C15 C16 1.184(3) . ?
C16 C17 1.461(4) . ?
C17 C18 1.495(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
O1 C2 C3 110.4(3) . . ?
O1 C2 C1 110.6(3) . . ?
C3 C2 C1 110.8(3) . . ?
C4 C3 C2 175.8(3) . . ?
C3 C4 C5 176.1(3) . . ?
C6 C5 C14 119.2(2) . . ?
C6 C5 C4 121.4(2) . . ?
C14 C5 C4 119.4(2) . . ?
C5 C6 C7 121.3(2) . . ?
C12 C7 C8 118.6(2) . . ?
C12 C7 C6 118.7(2) . . ?
C8 C7 C6 122.7(2) . . ?
C9 C8 C7 121.0(2) . . ?
C8 C9 C10 120.9(2) . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 C15 120.1(3) . . ?
C9 C10 C15 120.7(2) . . ?
C10 C11 C12 121.4(2) . . ?
C13 C12 C11 122.3(2) . . ?
C13 C12 C7 118.8(2) . . ?
C11 C12 C7 118.9(2) . . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 C5 120.9(2) . . ?
C16 C15 C10 177.6(3) . . ?
C15 C16 C17 178.3(3) . . ?
O2 C17 C16 109.8(2) . . ?
O2 C17 C18 108.0(2) . . ?
C16 C17 C18 112.4(3) . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_180K
_database_code_depnum_ccdc_archive 'CCDC 1855850'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6915(5)
_cell_length_b                   7.4628(5)
_cell_length_c                   28.143(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1195.37(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3459
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.20

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12778
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_full        25.000
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2977
_reflns_number_gt                2164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0347P)²+0.1170P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.8954(5) 0.3655(4) 0.06761(9) 0.0499(7) Uani 1 1 d . . . . .
H1A H 0.962570 0.361157 0.035571 0.075 Uiso 1 1 calc R U . . .
H1B H 0.883938 0.243722 0.080414 0.075 Uiso 1 1 calc R U . . .
H1C H 0.996697 0.437951 0.088213 0.075 Uiso 1 1 calc R U . . .
C2 C 0.6533(4) 0.4485(3) 0.06553(7) 0.0282(5) Uani 1 1 d . . . . .
H2 H 0.551921 0.372989 0.044511 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5452(4) 0.4565(3) 0.11292(7) 0.0275(5) Uani 1 1 d . . . . .
C4 C 0.4611(4) 0.4530(3) 0.15157(7) 0.0270(5) Uani 1 1 d . . . . .
C5 C 0.3563(4) 0.4428(3) 0.19826(7) 0.0234(5) Uani 1 1 d . . . . .
C6 C 0.1398(4) 0.3580(3) 0.20437(7) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.059396 0.310149 0.177646 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0422(4) 0.3434(3) 0.24902(7) 0.0245(5) Uani 1 1 d . . . . .
H7 H -0.104787 0.284804 0.252804 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1561(4) 0.4133(2) 0.28861(7) 0.0226(5) Uani 1 1 d . . . . .
C9 C 0.3714(4) 0.4983(3) 0.28256(7) 0.0260(5) Uani 1 1 d . . . . .
H9 H 0.451151 0.546408 0.309338 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4703(4) 0.5135(3) 0.23788(7) 0.0254(5) Uani 1 1 d . . . . .
H10 H 0.616997 0.572546 0.234147 0.030 Uiso 1 1 calc R U . . .
C11 C 0.0474(4) 0.3975(3) 0.33456(7) 0.0266(5) Uani 1 1 d . . . . .
C12 C -0.0528(4) 0.3808(3) 0.37157(7) 0.0274(5) Uani 1 1 d . . . . .
C13 C -0.1756(4) 0.3584(3) 0.41721(7) 0.0272(5) Uani 1 1 d . . . . .
H13 H -0.244431 0.235164 0.418469 0.033 Uiso 1 1 calc R U . . .
C14 C -0.3698(4) 0.4932(3) 0.42391(8) 0.0351(6) Uani 1 1 d . . . . .
H14A H -0.442739 0.475504 0.455103 0.053 Uiso 1 1 calc R U . . .
H14B H -0.488176 0.477127 0.398988 0.053 Uiso 1 1 calc R U . . .
H14C H -0.304750 0.614539 0.422005 0.053 Uiso 1 1 calc R U . . .
O1 O 0.6647(3) 0.62575(19) 0.04591(6) 0.0291(4) Uani 1 1 d . . . . .
O2 O -0.0121(3) 0.3782(2) 0.45571(5) 0.0329(4) Uani 1 1 d . . . . .
H1 H 0.623(5) 0.623(4) 0.0169(10) 0.056(8) Uiso 1 1 d . . . . .
H2A H 0.107(6) 0.295(4) 0.4511(10) 0.071(10) 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
C1 C2 1.512(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.435(2) . ?
C2 C3 1.470(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.189(3) . ?
C4 C5 1.445(3) . ?
C5 C10 1.394(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 C11 1.438(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.194(3) . ?
C12 C13 1.472(3) . ?
C13 O2 1.436(2) . ?
C13 C14 1.506(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1 H1 0.85(3) . ?
O2 H2A 0.93(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.29(16) . . ?
O1 C2 C1 110.55(19) . . ?
C3 C2 C1 111.28(18) . . ?
O1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C4 C3 C2 176.2(2) . . ?
C3 C4 C5 178.2(2) . . ?
C10 C5 C6 118.95(18) . . ?
C10 C5 C4 121.04(19) . . ?
C6 C5 C4 120.00(19) . . ?
C7 C6 C5 120.25(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.87(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 118.95(18) . . ?
C7 C8 C11 119.29(19) . . ?
C9 C8 C11 121.75(18) . . ?
C10 C9 C8 120.49(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.49(19) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C8 176.6(2) . . ?
C11 C12 C13 179.4(2) . . ?
O2 C13 C12 109.81(17) . . ?
O2 C13 C14 108.19(16) . . ?
C12 C13 C14 112.44(18) . . ?
O2 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 109.5(18) . . ?
C13 O2 H2A 107.3(17) . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_250K
_database_code_depnum_ccdc_archive 'CCDC 1855864'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9061(3)
_cell_length_b                   7.3412(5)
_cell_length_c                   32.9746(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1429.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    5655
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.72

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8656
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3492
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_fraction_full    0.975

_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-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0763P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 786 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
O1 O 0.3614(3) 0.6312(3) 0.95960(5) 0.0402(5) Uani 1 1 d . . . . .
O2 O 0.9857(3) 0.3773(3) 0.53626(5) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.1422(5) 0.3685(5) 0.93937(9) 0.0682(10) Uani 1 1 d . . . . .
H1A H 0.076234 0.362213 0.966271 0.102 Uiso 1 1 calc R U . . .
H1B H 0.155145 0.246549 0.928262 0.102 Uiso 1 1 calc R U . . .
H1C H 0.046103 0.441618 0.921932 0.102 Uiso 1 1 calc R U . . .
C2 C 0.3753(4) 0.4545(4) 0.94192(7) 0.0395(6) Uani 1 1 d . . . . .
H2 H 0.471956 0.377148 0.959387 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4799(4) 0.4659(4) 0.90152(6) 0.0377(6) Uani 1 1 d . . . . .
C4 C 0.5601(4) 0.4631(4) 0.86841(6) 0.0367(6) Uani 1 1 d . . . . .
C5 C 0.6607(4) 0.4473(4) 0.82878(6) 0.0315(6) Uani 1 1 d . . . . .
C6 C 0.5483(4) 0.5005(3) 0.79458(6) 0.0299(5) Uani 1 1 d . . . . .
H6 H 0.406746 0.557950 0.797011 0.036 Uiso 1 1 calc R U . . .
C7 C 0.6411(3) 0.4709(3) 0.75554(6) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.5247(4) 0.5183(3) 0.71945(6) 0.0300(5) Uani 1 1 d . . . . .
H8 H 0.380578 0.572098 0.721131 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6187(4) 0.4870(4) 0.68239(6) 0.0334(6) Uani 1 1 d . . . . .
H9 H 0.538463 0.519098 0.658829 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8355(4) 0.4069(3) 0.67893(6) 0.0307(6) Uani 1 1 d . . . . .
C11 C 0.9489(4) 0.3561(3) 0.71337(6) 0.0278(5) Uani 1 1 d . . . . .
H11 H 1.090812 0.299065 0.711048 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8571(3) 0.3875(3) 0.75222(6) 0.0244(5) Uani 1 1 d . . . . .
C13 C 0.9735(4) 0.3389(3) 0.78809(6) 0.0306(5) Uani 1 1 d . . . . .
H13 H 1.118518 0.286682 0.786307 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8783(4) 0.3666(4) 0.82511(6) 0.0336(6) Uani 1 1 d . . . . .
H14 H 0.957566 0.331852 0.848595 0.040 Uiso 1 1 calc R U . . .
C15 C 0.9384(4) 0.3835(4) 0.63978(7) 0.0359(6) Uani 1 1 d . . . . .
C16 C 1.0309(4) 0.3702(4) 0.60796(6) 0.0380(6) Uani 1 1 d . . . . .
C17 C 1.1464(4) 0.3545(4) 0.56851(7) 0.0372(6) Uani 1 1 d . . . . .
H17 H 1.215130 0.231890 0.566363 0.045 Uiso 1 1 calc R U . . .
C18 C 1.3291(4) 0.4959(4) 0.56339(8) 0.0505(8) Uani 1 1 d . . . . .
H18A H 1.395807 0.484426 0.536633 0.076 Uiso 1 1 calc R U . . .
H18B H 1.445003 0.477780 0.583832 0.076 Uiso 1 1 calc R U . . .
H18C H 1.263999 0.616435 0.566407 0.076 Uiso 1 1 calc R U . . .
H1 H 0.398(6) 0.623(5) 0.9830(13) 0.094(13) Uiso 1 1 d . . . . .
H2A H 0.868(7) 0.302(5) 0.5387(11) 0.092(14) 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 1.425(3) . ?
O2 C17 1.435(3) . ?
C1 C2 1.517(4) . ?
C2 C3 1.471(3) . ?
C3 C4 1.190(3) . ?
C4 C5 1.440(3) . ?
C5 C6 1.366(3) . ?
C5 C14 1.420(3) . ?
C6 C7 1.416(3) . ?
C7 C8 1.417(3) . ?
C7 C12 1.419(3) . ?
C8 C9 1.362(3) . ?
C9 C10 1.414(3) . ?
C10 C11 1.370(3) . ?
C10 C15 1.437(3) . ?
C11 C12 1.410(3) . ?
C12 C13 1.414(3) . ?
C13 C14 1.359(3) . ?
C15 C16 1.187(3) . ?
C16 C17 1.473(3) . ?
C17 C18 1.507(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
O1 C2 C3 110.0(2) . . ?
O1 C2 C1 110.5(2) . . ?
C3 C2 C1 110.8(2) . . ?
C4 C3 C2 175.5(3) . . ?
C3 C4 C5 176.2(3) . . ?
C6 C5 C14 119.26(19) . . ?
C6 C5 C4 121.7(2) . . ?
C14 C5 C4 119.0(2) . . ?
C5 C6 C7 121.3(2) . . ?
C6 C7 C8 122.55(19) . . ?
C6 C7 C12 118.94(18) . . ?
C8 C7 C12 118.49(18) . . ?
C9 C8 C7 121.0(2) . . ?
C8 C9 C10 120.8(2) . . ?
C11 C10 C9 119.28(19) . . ?
C11 C10 C15 120.4(2) . . ?
C9 C10 C15 120.3(2) . . ?
C10 C11 C12 121.37(19) . . ?
C11 C12 C13 122.11(19) . . ?
C11 C12 C7 119.09(19) . . ?
C13 C12 C7 118.80(18) . . ?
C14 C13 C12 120.8(2) . . ?
C13 C14 C5 120.9(2) . . ?
C16 C15 C10 176.8(3) . . ?
C15 C16 C17 179.7(3) . . ?
O2 C17 C16 109.80(19) . . ?
O2 C17 C18 108.1(2) . . ?
C16 C17 C18 112.1(2) . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_200K
_database_code_depnum_ccdc_archive 'CCDC 1855863'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8987(3)
_cell_length_b                   7.2946(5)
_cell_length_c                   32.966(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1418.46(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6231
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.09

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8484
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3423
_reflns_number_gt                2578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.960

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0479P)²+0.2403P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 851 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3423
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.3594(3) 0.6328(2) 0.95954(5) 0.0311(4) Uani 1 1 d . . . . .
O2 O 0.9884(3) 0.3794(3) 0.53601(5) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.1371(5) 0.3705(5) 0.93880(8) 0.0535(9) Uani 1 1 d . . . . .
H1A H 0.070904 0.361881 0.966000 0.080 Uiso 1 1 calc R U . . .
H1B H 0.148348 0.247581 0.926950 0.080 Uiso 1 1 calc R U . . .
H1C H 0.040447 0.447429 0.921631 0.080 Uiso 1 1 calc R U . . .
C2 C 0.3717(4) 0.4548(4) 0.94161(7) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.468285 0.374918 0.959179 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4768(4) 0.4669(4) 0.90123(7) 0.0303(6) Uani 1 1 d . . . . .
C4 C 0.5581(4) 0.4649(4) 0.86812(7) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.6600(4) 0.4480(3) 0.82854(6) 0.0255(5) Uani 1 1 d . . . . .
C6 C 0.5466(4) 0.5010(3) 0.79411(6) 0.0243(5) Uani 1 1 d . . . . .
H6 H 0.402637 0.558526 0.796435 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6412(3) 0.4712(3) 0.75519(6) 0.0200(5) Uani 1 1 d . . . . .
C8 C 0.5243(4) 0.5182(3) 0.71907(6) 0.0236(5) Uani 1 1 d . . . . .
H8 H 0.377974 0.572110 0.720690 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6198(4) 0.4868(4) 0.68200(6) 0.0267(5) Uani 1 1 d . . . . .
H9 H 0.539213 0.519455 0.658111 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8371(4) 0.4064(3) 0.67869(6) 0.0245(5) Uani 1 1 d . . . . .
C11 C 0.9512(4) 0.3561(3) 0.71318(6) 0.0223(5) Uani 1 1 d . . . . .
H11 H 1.095447 0.299124 0.710914 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8580(3) 0.3875(3) 0.75202(6) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.9741(4) 0.3388(3) 0.78803(6) 0.0235(5) Uani 1 1 d . . . . .
H13 H 1.120812 0.285635 0.786321 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8778(4) 0.3672(4) 0.82521(6) 0.0272(5) Uani 1 1 d . . . . .
H14 H 0.957447 0.332402 0.849042 0.033 Uiso 1 1 calc R U . . .
C15 C 0.9415(4) 0.3833(4) 0.63957(7) 0.0287(6) Uani 1 1 d . . . . .
C16 C 1.0342(4) 0.3701(4) 0.60775(6) 0.0301(6) Uani 1 1 d . . . . .
C17 C 1.1498(4) 0.3550(4) 0.56825(6) 0.0300(6) Uani 1 1 d . . . . .
H17 H 1.218674 0.230144 0.565899 0.036 Uiso 1 1 calc R U . . .
C18 C 1.3331(4) 0.4967(4) 0.56317(8) 0.0391(7) Uani 1 1 d . . . . .
H18A H 1.400265 0.485353 0.536098 0.059 Uiso 1 1 calc R U . . .
H18B H 1.450580 0.477649 0.583771 0.059 Uiso 1 1 calc R U . . .
H18C H 1.267866 0.619431 0.566350 0.059 Uiso 1 1 calc R U . . .
H2A H 0.877(6) 0.299(5) 0.5395(9) 0.061(11) Uiso 1 1 d . . . . .
H1 H 0.404(6) 0.623(5) 0.9840(10) 0.062(10) 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 1.429(3) . ?
O1 H1 0.85(3) . ?
O2 C17 1.438(3) . ?
O2 H2A 0.89(4) . ?
C1 C2 1.517(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.471(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.192(3) . ?
C4 C5 1.442(3) . ?
C5 C6 1.373(3) . ?
C5 C14 1.418(3) . ?
C6 C7 1.416(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.418(3) . ?
C7 C12 1.421(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.414(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(3) . ?
C10 C15 1.439(3) . ?
C11 C12 1.412(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(3) . ?
C13 C14 1.367(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.187(3) . ?
C16 C17 1.474(3) . ?
C17 C18 1.506(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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(2) . . ?
C17 O2 H2A 108(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 110.0(2) . . ?
O1 C2 C1 110.3(2) . . ?
C3 C2 C1 110.7(2) . . ?
O1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C4 C3 C2 175.7(3) . . ?
C3 C4 C5 175.7(3) . . ?
C6 C5 C14 119.66(19) . . ?
C6 C5 C4 121.4(2) . . ?
C14 C5 C4 118.9(2) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 122.1(2) . . ?
C6 C7 C12 119.18(19) . . ?
C8 C7 C12 118.67(19) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.47(19) . . ?
C11 C10 C15 120.1(2) . . ?
C9 C10 C15 120.4(2) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.07(19) . . ?
C11 C12 C7 119.13(19) . . ?
C13 C12 C7 118.80(18) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C5 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C5 C14 H14 119.7 . . ?
C16 C15 C10 177.1(3) . . ?
C15 C16 C17 179.7(3) . . ?
O2 C17 C16 109.72(19) . . ?
O2 C17 C18 108.0(2) . . ?
C16 C17 C18 112.2(2) . . ?
O2 C17 H17 109.0 . . ?
C16 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_320K
_database_code_depnum_ccdc_archive 'CCDC 1855856'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7090(7)
_cell_length_b                   7.6146(8)
_cell_length_c                   28.123(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1222.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    2320
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.48

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13150
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.000
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3060
_reflns_number_gt                1492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.997
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0389P)²+0.0652P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1593
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.8832(7) 0.3628(5) 0.06556(13) 0.0978(14) Uani 1 1 d . . . . .
H1A H 0.947702 0.359925 0.034042 0.147 Uiso 1 1 calc R U . . .
H1B H 0.868358 0.245076 0.077412 0.147 Uiso 1 1 calc R U . . .
H1C H 0.985064 0.428694 0.086034 0.147 Uiso 1 1 calc R U . . .
C2 C 0.6454(6) 0.4486(4) 0.06428(10) 0.0533(8) Uani 1 1 d . . . . .
H2 H 0.543289 0.378999 0.043549 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5400(5) 0.4551(4) 0.11167(11) 0.0525(8) Uani 1 1 d . . . . .
C4 C 0.4579(5) 0.4507(4) 0.15032(11) 0.0528(9) Uani 1 1 d . . . . .
C5 C 0.3547(5) 0.4409(4) 0.19711(10) 0.0450(7) Uani 1 1 d . . . . .
C6 C 0.1430(6) 0.3573(4) 0.20376(10) 0.0526(8) Uani 1 1 d . . . . .
H6 H 0.064191 0.310112 0.177790 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0476(5) 0.3430(3) 0.24843(10) 0.0483(8) Uani 1 1 d . . . . .
H7 H -0.094910 0.285705 0.252447 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1609(5) 0.4130(3) 0.28741(9) 0.0426(7) Uani 1 1 d . . . . .
C9 C 0.3714(5) 0.4976(4) 0.28089(10) 0.0514(8) Uani 1 1 d . . . . .
H9 H 0.448781 0.545891 0.306886 0.062 Uiso 1 1 calc R U . . .
C10 C 0.4685(5) 0.5115(4) 0.23618(10) 0.0502(8) Uani 1 1 d . . . . .
H10 H 0.611218 0.568628 0.232220 0.060 Uiso 1 1 calc R U . . .
C11 C 0.0541(5) 0.3972(4) 0.33360(11) 0.0506(8) Uani 1 1 d . . . . .
C12 C -0.0437(5) 0.3802(4) 0.37057(11) 0.0526(8) Uani 1 1 d . . . . .
C13 C -0.1679(5) 0.3575(4) 0.41592(10) 0.0531(8) Uani 1 1 d . . . . .
H13 H -0.237020 0.239687 0.416712 0.064 Uiso 1 1 calc R U . . .
C14 C -0.3590(5) 0.4905(5) 0.42272(11) 0.0705(10) Uani 1 1 d . . . . .
H14A H -0.436792 0.469232 0.452433 0.106 Uiso 1 1 calc R U . . .
H14B H -0.469953 0.480960 0.397189 0.106 Uiso 1 1 calc R U . . .
H14C H -0.292620 0.606291 0.422876 0.106 Uiso 1 1 calc R U . . .
O1 O 0.6612(4) 0.6219(3) 0.04536(9) 0.0572(6) Uani 1 1 d . . . . .
O2 O -0.0073(4) 0.3740(3) 0.45463(7) 0.0641(7) Uani 1 1 d . . . . .
H1 H 0.626(6) 0.623(5) 0.0181(13) 0.093(15) Uiso 1 1 d . . . . .
H2A H 0.103(7) 0.293(4) 0.4491(12) 0.091(14) 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
C1 C2 1.507(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.426(3) . ?
C2 C3 1.463(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.184(4) . ?
C4 C5 1.444(4) . ?
C5 C6 1.379(4) . ?
C5 C10 1.385(4) . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 C11 1.440(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.187(4) . ?
C12 C13 1.469(4) . ?
C13 O2 1.429(3) . ?
C13 C14 1.501(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.79(3) . ?
O2 H2A 0.90(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.5(2) . . ?
O1 C2 C1 110.7(3) . . ?
C3 C2 C1 111.3(3) . . ?
O1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C4 C3 C2 176.3(3) . . ?
C3 C4 C5 178.4(3) . . ?
C6 C5 C10 118.9(3) . . ?
C6 C5 C4 120.4(3) . . ?
C10 C5 C4 120.7(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 C11 122.0(3) . . ?
C7 C8 C11 119.1(3) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C8 176.6(3) . . ?
C11 C12 C13 179.0(3) . . ?
O2 C13 C12 110.0(2) . . ?
O2 C13 C14 108.1(2) . . ?
C12 C13 C14 112.4(3) . . ?
O2 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 111(3) . . ?
C13 O2 H2A 105(2) . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_300K
_database_code_depnum_ccdc_archive 'CCDC 1855865'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9146(3)
_cell_length_b                   7.3912(5)
_cell_length_c                   32.9799(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1441.75(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    6100
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.69

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8646
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.470
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3491
_reflns_number_gt                2384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.967

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0496P)²+0.1980P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.3634(3) 0.6294(3) 0.95971(5) 0.0487(5) Uani 1 1 d . . . . .
O2 O 0.9838(4) 0.3757(3) 0.53656(5) 0.0566(6) Uani 1 1 d . . . . .
C1 C 0.1471(6) 0.3665(5) 0.93992(10) 0.0844(12) Uani 1 1 d . . . . .
H1A H 0.082933 0.359886 0.966618 0.127 Uiso 1 1 calc R U . . .
H1B H 0.160984 0.246730 0.928929 0.127 Uiso 1 1 calc R U . . .
H1C H 0.050642 0.437609 0.922771 0.127 Uiso 1 1 calc R U . . .
C2 C 0.3789(5) 0.4538(4) 0.94220(7) 0.0483(7) Uani 1 1 d . . . . .
H2 H 0.475628 0.378860 0.959530 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4828(5) 0.4648(4) 0.90179(7) 0.0463(6) Uani 1 1 d . . . . .
C4 C 0.5619(4) 0.4622(4) 0.86874(7) 0.0453(6) Uani 1 1 d . . . . .
C5 C 0.6625(4) 0.4464(3) 0.82903(6) 0.0378(6) Uani 1 1 d . . . . .
C6 C 0.5490(4) 0.4993(3) 0.79496(6) 0.0356(5) Uani 1 1 d . . . . .
H6 H 0.408762 0.555140 0.797464 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6415(3) 0.4705(3) 0.75589(6) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.5245(4) 0.5178(3) 0.71989(6) 0.0370(6) Uani 1 1 d . . . . .
H8 H 0.382171 0.570817 0.721633 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6176(4) 0.4868(4) 0.68290(6) 0.0408(6) Uani 1 1 d . . . . .
H9 H 0.537830 0.518414 0.659656 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8336(4) 0.4071(3) 0.67917(6) 0.0366(6) Uani 1 1 d . . . . .
C11 C 0.9476(4) 0.3566(3) 0.71356(6) 0.0342(5) Uani 1 1 d . . . . .
H11 H 1.087819 0.300638 0.711186 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8567(3) 0.3877(3) 0.75241(6) 0.0298(5) Uani 1 1 d . . . . .
C13 C 0.9729(4) 0.3389(3) 0.78814(6) 0.0370(6) Uani 1 1 d . . . . .
H13 H 1.116027 0.287349 0.786271 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8788(4) 0.3660(4) 0.82525(6) 0.0419(6) Uani 1 1 d . . . . .
H14 H 0.957313 0.331297 0.848411 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9356(4) 0.3839(4) 0.63997(7) 0.0446(6) Uani 1 1 d . . . . .
C16 C 1.0271(5) 0.3698(4) 0.60820(6) 0.0463(7) Uani 1 1 d . . . . .
C17 C 1.1428(4) 0.3541(4) 0.56887(7) 0.0459(6) Uani 1 1 d . . . . .
H17 H 1.211198 0.233630 0.566879 0.055 Uiso 1 1 calc R U . . .
C18 C 1.3244(5) 0.4939(5) 0.56371(8) 0.0622(8) Uani 1 1 d . . . . .
H18A H 1.390085 0.482728 0.537210 0.093 Uiso 1 1 calc R U . . .
H18B H 1.439238 0.476151 0.583896 0.093 Uiso 1 1 calc R U . . .
H18C H 1.260138 0.612447 0.566727 0.093 Uiso 1 1 calc R U . . .
H1 H 0.413(7) 0.620(5) 0.9838(12) 0.103(13) Uiso 1 1 d . . . . .
H2A H 0.871(6) 0.299(5) 0.5396(10) 0.091(13) 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 1.424(3) . ?
O2 C17 1.430(3) . ?
C1 C2 1.517(4) . ?
C2 C3 1.470(3) . ?
C3 C4 1.187(3) . ?
C4 C5 1.443(3) . ?
C5 C6 1.366(3) . ?
C5 C14 1.416(3) . ?
C6 C7 1.416(3) . ?
C7 C12 1.417(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.358(3) . ?
C9 C10 1.412(3) . ?
C10 C11 1.371(3) . ?
C10 C15 1.437(3) . ?
C11 C12 1.408(3) . ?
C12 C13 1.411(3) . ?
C13 C14 1.359(3) . ?
C15 C16 1.184(3) . ?
C16 C17 1.471(3) . ?
C17 C18 1.500(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
O1 C2 C3 110.1(2) . . ?
O1 C2 C1 110.4(2) . . ?
C3 C2 C1 110.9(2) . . ?
C4 C3 C2 175.6(3) . . ?
C3 C4 C5 176.1(3) . . ?
C6 C5 C14 119.45(19) . . ?
C6 C5 C4 121.4(2) . . ?
C14 C5 C4 119.1(2) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C7 C12 119.06(19) . . ?
C6 C7 C8 122.4(2) . . ?
C12 C7 C8 118.50(18) . . ?
C9 C8 C7 120.8(2) . . ?
C8 C9 C10 121.0(2) . . ?
C11 C10 C9 119.11(19) . . ?
C11 C10 C15 120.3(2) . . ?
C9 C10 C15 120.5(2) . . ?
C10 C11 C12 121.3(2) . . ?
C11 C12 C13 122.11(19) . . ?
C11 C12 C7 119.16(19) . . ?
C13 C12 C7 118.73(18) . . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 C5 120.7(2) . . ?
C16 C15 C10 177.1(3) . . ?
C15 C16 C17 179.3(3) . . ?
O2 C17 C16 110.0(2) . . ?
O2 C17 C18 108.0(2) . . ?
C16 C17 C18 112.2(2) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_90K
_database_code_depnum_ccdc_archive 'CCDC 1855860'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6838(4)
_cell_length_b                   7.3834(4)
_cell_length_c                   28.139(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1180.88(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4287
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.75

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12631
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.852
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2922
_reflns_number_gt                2481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.994
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0398P)²+0.1550P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2922
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
C1 C 0.9025(4) 0.3667(3) 0.06864(8) 0.0255(5) Uani 1 1 d . . . . .
H1A H 0.971061 0.362835 0.036709 0.038 Uiso 1 1 calc R U . . .
H1B H 0.891975 0.243446 0.081407 0.038 Uiso 1 1 calc R U . . .
H1C H 1.002092 0.440574 0.089426 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6579(4) 0.4491(2) 0.06615(7) 0.0157(4) Uani 1 1 d . . . . .
H2 H 0.557931 0.371326 0.045205 0.019 Uiso 1 1 calc R U . . .
C3 C 0.5489(4) 0.4570(2) 0.11346(7) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.4635(3) 0.4538(2) 0.15215(6) 0.0139(4) Uani 1 1 d . . . . .
C5 C 0.3572(3) 0.4439(2) 0.19872(6) 0.0125(4) Uani 1 1 d . . . . .
C6 C 0.1386(3) 0.3583(2) 0.20457(6) 0.0141(4) Uani 1 1 d . . . . .
H6 H 0.058655 0.310420 0.177718 0.017 Uiso 1 1 calc R U . . .
C7 C 0.0395(3) 0.3432(2) 0.24914(7) 0.0127(4) Uani 1 1 d . . . . .
H7 H -0.108347 0.284753 0.252721 0.015 Uiso 1 1 calc R U . . .
C8 C 0.1539(3) 0.4129(2) 0.28903(6) 0.0122(4) Uani 1 1 d . . . . .
C9 C 0.3713(3) 0.4984(2) 0.28338(6) 0.0137(4) Uani 1 1 d . . . . .
H9 H 0.451001 0.545973 0.310295 0.016 Uiso 1 1 calc R U . . .
C10 C 0.4713(4) 0.5139(2) 0.23859(6) 0.0131(4) Uani 1 1 d . . . . .
H10 H 0.618862 0.572825 0.235036 0.016 Uiso 1 1 calc R U . . .
C11 C 0.0441(3) 0.3967(2) 0.33485(7) 0.0145(4) Uani 1 1 d . . . . .
C12 C -0.0573(3) 0.3807(3) 0.37184(6) 0.0150(4) Uani 1 1 d . . . . .
C13 C -0.1797(3) 0.3586(3) 0.41762(6) 0.0138(4) Uani 1 1 d . . . . .
H13 H -0.247490 0.233761 0.419176 0.017 Uiso 1 1 calc R U . . .
C14 C -0.3761(4) 0.4948(3) 0.42427(7) 0.0186(4) Uani 1 1 d . . . . .
H14A H -0.446021 0.479288 0.455852 0.028 Uiso 1 1 calc R U . . .
H14B H -0.496842 0.475524 0.399923 0.028 Uiso 1 1 calc R U . . .
H14C H -0.312715 0.617714 0.421353 0.028 Uiso 1 1 calc R U . . .
O1 O 0.6672(2) 0.62781(17) 0.04610(5) 0.0152(3) Uani 1 1 d . . . . .
O2 O -0.0151(2) 0.38091(19) 0.45616(4) 0.0173(3) Uani 1 1 d . . . . .
H1 H 0.626(5) 0.622(4) 0.0172(10) 0.043(8) Uiso 1 1 d . . . . .
H2A H 0.099(5) 0.299(3) 0.4523(9) 0.042(8) 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
C1 C2 1.519(3) . ?
C2 O1 1.436(2) . ?
C2 C3 1.470(3) . ?
C3 C4 1.192(3) . ?
C4 C5 1.445(3) . ?
C5 C10 1.395(3) . ?
C5 C6 1.403(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.396(3) . ?
C8 C11 1.437(3) . ?
C9 C10 1.387(3) . ?
C11 C12 1.196(3) . ?
C12 C13 1.473(3) . ?
C13 O2 1.442(2) . ?
C13 C14 1.514(3) . ?

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 C2 C3 109.58(15) . . ?
O1 C2 C1 110.65(16) . . ?
C3 C2 C1 111.08(16) . . ?
C4 C3 C2 176.48(19) . . ?
C3 C4 C5 178.10(19) . . ?
C10 C5 C6 118.95(16) . . ?
C10 C5 C4 121.06(17) . . ?
C6 C5 C4 119.96(17) . . ?
C7 C6 C5 120.30(17) . . ?
C6 C7 C8 120.74(17) . . ?
C7 C8 C9 119.16(16) . . ?
C7 C8 C11 119.23(17) . . ?
C9 C8 C11 121.61(16) . . ?
C10 C9 C8 120.23(17) . . ?
C9 C10 C5 120.61(17) . . ?
C12 C11 C8 176.8(2) . . ?
C11 C12 C13 179.1(2) . . ?
O2 C13 C12 109.79(15) . . ?
O2 C13 C14 108.04(15) . . ?
C12 C13 C14 112.50(16) . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_350K
_database_code_depnum_ccdc_archive 'CCDC 1855866'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9244(3)
_cell_length_b                   7.4427(5)
_cell_length_c                   32.968(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1453.69(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    5383
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.47

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6561
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8778
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3552
_reflns_number_gt                2196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.978

_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-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0757P)²+0.0180P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.3654(3) 0.6273(3) 0.95980(5) 0.0604(6) Uani 1 1 d . . . . .
O2 O 0.9812(4) 0.3732(3) 0.53693(5) 0.0707(7) Uani 1 1 d . . . . .
C1 C 0.1530(7) 0.3651(6) 0.94057(11) 0.1042(14) Uani 1 1 d . . . . .
H1A H 0.088802 0.360023 0.967281 0.156 Uiso 1 1 calc R U . . .
H1B H 0.168484 0.245444 0.930038 0.156 Uiso 1 1 calc R U . . .
H1C H 0.056073 0.433646 0.923119 0.156 Uiso 1 1 calc R U . . .
C2 C 0.3829(5) 0.4535(4) 0.94258(7) 0.0604(8) Uani 1 1 d . . . . .
H2 H 0.480526 0.380403 0.960002 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4856(5) 0.4634(4) 0.90215(7) 0.0575(8) Uani 1 1 d . . . . .
C4 C 0.5643(5) 0.4612(4) 0.86911(7) 0.0558(7) Uani 1 1 d . . . . .
C5 C 0.6639(4) 0.4458(4) 0.82933(6) 0.0473(7) Uani 1 1 d . . . . .
C6 C 0.5508(4) 0.4985(4) 0.79542(6) 0.0442(6) Uani 1 1 d . . . . .
H6 H 0.411137 0.554352 0.798055 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6413(3) 0.4699(3) 0.75626(6) 0.0379(6) Uani 1 1 d . . . . .
C8 C 0.5249(4) 0.5176(4) 0.72041(7) 0.0452(6) Uani 1 1 d . . . . .
H8 H 0.383286 0.570785 0.722264 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6166(4) 0.4869(4) 0.68332(7) 0.0503(7) Uani 1 1 d . . . . .
H9 H 0.536731 0.518955 0.660138 0.060 Uiso 1 1 calc R U . . .
C10 C 0.8313(4) 0.4071(4) 0.67952(7) 0.0455(6) Uani 1 1 d . . . . .
C11 C 0.9458(4) 0.3570(3) 0.71376(7) 0.0429(6) Uani 1 1 d . . . . .
H11 H 1.085876 0.301647 0.711276 0.051 Uiso 1 1 calc R U . . .
C12 C 0.8556(4) 0.3874(3) 0.75266(6) 0.0376(6) Uani 1 1 d . . . . .
C13 C 0.9721(4) 0.3388(3) 0.78832(7) 0.0458(6) Uani 1 1 d . . . . .
H13 H 1.114962 0.287696 0.786380 0.055 Uiso 1 1 calc R U . . .
C14 C 0.8788(4) 0.3653(4) 0.82538(7) 0.0517(7) Uani 1 1 d . . . . .
H14 H 0.957191 0.330144 0.848492 0.062 Uiso 1 1 calc R U . . .
C15 C 0.9330(5) 0.3838(4) 0.64026(7) 0.0545(7) Uani 1 1 d . . . . .
C16 C 1.0235(5) 0.3696(4) 0.60840(7) 0.0575(8) Uani 1 1 d . . . . .
C17 C 1.1398(5) 0.3537(4) 0.56928(7) 0.0569(8) Uani 1 1 d . . . . .
H17 H 1.208612 0.234207 0.567500 0.068 Uiso 1 1 calc R U . . .
C18 C 1.3201(5) 0.4919(5) 0.56412(9) 0.0775(10) Uani 1 1 d . . . . .
H18A H 1.390314 0.477199 0.538082 0.116 Uiso 1 1 calc R U . . .
H18B H 1.431283 0.477778 0.585059 0.116 Uiso 1 1 calc R U . . .
H18C H 1.254696 0.609661 0.565883 0.116 Uiso 1 1 calc R U . . .
H1 H 0.406(7) 0.616(6) 0.9856(12) 0.113(13) Uiso 1 1 d . . . . .
H2A H 0.855(7) 0.293(6) 0.5390(11) 0.113(15) 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 1.416(3) . ?
O2 C17 1.429(3) . ?
C1 C2 1.514(5) . ?
C2 C3 1.467(3) . ?
C3 C4 1.185(3) . ?
C4 C5 1.443(3) . ?
C5 C6 1.361(3) . ?
C5 C14 1.413(4) . ?
C6 C7 1.414(3) . ?
C7 C8 1.414(3) . ?
C7 C12 1.415(3) . ?
C8 C9 1.357(3) . ?
C9 C10 1.410(4) . ?
C10 C11 1.369(3) . ?
C10 C15 1.438(3) . ?
C11 C12 1.407(3) . ?
C12 C13 1.411(3) . ?
C13 C14 1.356(3) . ?
C15 C16 1.184(3) . ?
C16 C17 1.467(3) . ?
C17 C18 1.493(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
O1 C2 C3 110.4(2) . . ?
O1 C2 C1 110.4(3) . . ?
C3 C2 C1 110.8(2) . . ?
C4 C3 C2 176.1(3) . . ?
C3 C4 C5 176.1(3) . . ?
C6 C5 C14 119.3(2) . . ?
C6 C5 C4 121.5(2) . . ?
C14 C5 C4 119.1(2) . . ?
C5 C6 C7 121.3(2) . . ?
C8 C7 C6 122.7(2) . . ?
C8 C7 C12 118.43(19) . . ?
C6 C7 C12 118.8(2) . . ?
C9 C8 C7 121.1(2) . . ?
C8 C9 C10 120.8(2) . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 C15 120.1(2) . . ?
C9 C10 C15 120.6(2) . . ?
C10 C11 C12 121.3(2) . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 C7 119.1(2) . . ?
C13 C12 C7 118.69(19) . . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 C5 120.8(2) . . ?
C16 C15 C10 177.3(3) . . ?
C15 C16 C17 178.8(3) . . ?
O2 C17 C16 109.8(2) . . ?
O2 C17 C18 108.4(2) . . ?
C16 C17 C18 112.4(2) . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_150K
_database_code_depnum_ccdc_archive 'CCDC 1855862'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8912(4)
_cell_length_b                   7.2496(5)
_cell_length_c                   32.950(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1407.27(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6772
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.13

_exptl_crystal_description       'HEXAGONAL PLATE'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8332
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3364
_reflns_number_gt                2677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.946

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0490P)²+0.3690P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.3571(3) 0.6345(2) 0.95947(5) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.9909(3) 0.3818(3) 0.53580(5) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.1322(5) 0.3724(5) 0.93839(8) 0.0394(7) Uani 1 1 d . . . . .
H1A H 0.065416 0.363469 0.965561 0.059 Uiso 1 1 calc R U . . .
H1B H 0.142572 0.248953 0.926398 0.059 Uiso 1 1 calc R U . . .
H1C H 0.036508 0.450832 0.921259 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3677(4) 0.4556(4) 0.94143(6) 0.0236(6) Uani 1 1 d . . . . .
H2 H 0.463365 0.374333 0.958991 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4740(4) 0.4679(4) 0.90096(7) 0.0225(5) Uani 1 1 d . . . . .
C4 C 0.5562(4) 0.4650(4) 0.86782(6) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.6589(4) 0.4490(3) 0.82831(6) 0.0191(5) Uani 1 1 d . . . . .
C6 C 0.5454(4) 0.5017(3) 0.79385(6) 0.0176(5) Uani 1 1 d . . . . .
H6 H 0.401016 0.559209 0.796100 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6408(3) 0.4713(3) 0.75488(6) 0.0160(5) Uani 1 1 d . . . . .
C8 C 0.5245(4) 0.5182(3) 0.71864(6) 0.0179(5) Uani 1 1 d . . . . .
H8 H 0.377812 0.572275 0.720171 0.022 Uiso 1 1 calc R U . . .
C9 C 0.6204(4) 0.4867(4) 0.68161(6) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.540061 0.519517 0.657684 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8389(4) 0.4056(3) 0.67840(6) 0.0181(5) Uani 1 1 d . . . . .
C11 C 0.9526(4) 0.3552(3) 0.71311(6) 0.0171(5) Uani 1 1 d . . . . .
H11 H 1.097093 0.297785 0.710957 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8584(3) 0.3873(3) 0.75197(6) 0.0150(5) Uani 1 1 d . . . . .
C13 C 0.9741(4) 0.3387(3) 0.78796(6) 0.0173(5) Uani 1 1 d . . . . .
H13 H 1.120794 0.284812 0.786322 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8774(4) 0.3682(4) 0.82512(6) 0.0212(5) Uani 1 1 d . . . . .
H14 H 0.957335 0.334160 0.849022 0.025 Uiso 1 1 calc R U . . .
C15 C 0.9442(4) 0.3829(4) 0.63947(6) 0.0208(5) Uani 1 1 d . . . . .
C16 C 1.0377(4) 0.3704(4) 0.60753(6) 0.0229(5) Uani 1 1 d . . . . .
C17 C 1.1523(4) 0.3557(4) 0.56796(6) 0.0217(5) Uani 1 1 d . . . . .
H17 H 1.220385 0.229867 0.565423 0.026 Uiso 1 1 calc R U . . .
C18 C 1.3374(4) 0.4980(4) 0.56290(7) 0.0288(6) Uani 1 1 d . . . . .
H18A H 1.401901 0.488546 0.535565 0.043 Uiso 1 1 calc R U . . .
H18B H 1.456809 0.476274 0.583053 0.043 Uiso 1 1 calc R U . . .
H18C H 1.273677 0.621630 0.566805 0.043 Uiso 1 1 calc R U . . .
H2A H 0.883(6) 0.305(4) 0.5393(9) 0.044(9) Uiso 1 1 d . . . . .
H1 H 0.404(6) 0.622(5) 0.9842(11) 0.056(10) 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 1.428(3) . ?
O1 H1 0.86(4) . ?
O2 C17 1.436(3) . ?
O2 H2A 0.86(3) . ?
C1 C2 1.516(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.476(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.195(3) . ?
C4 C5 1.440(3) . ?
C5 C6 1.372(3) . ?
C5 C14 1.418(3) . ?
C6 C7 1.419(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(3) . ?
C7 C12 1.422(3) . ?
C8 C9 1.364(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(3) . ?
C10 C15 1.434(3) . ?
C11 C12 1.415(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(3) . ?
C13 C14 1.367(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.191(3) . ?
C16 C17 1.472(3) . ?
C17 C18 1.511(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 106(2) . . ?
C17 O2 H2A 108(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.9(2) . . ?
O1 C2 C1 110.4(2) . . ?
C3 C2 C1 110.6(2) . . ?
O1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C4 C3 C2 175.4(3) . . ?
C3 C4 C5 176.3(3) . . ?
C6 C5 C14 119.75(19) . . ?
C6 C5 C4 121.4(2) . . ?
C14 C5 C4 118.8(2) . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 C12 118.77(19) . . ?
C6 C7 C12 119.01(19) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.35(19) . . ?
C11 C10 C15 120.2(2) . . ?
C9 C10 C15 120.4(2) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 121.96(19) . . ?
C13 C12 C7 119.01(19) . . ?
C11 C12 C7 119.03(19) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C5 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C5 C14 H14 119.7 . . ?
C16 C15 C10 177.1(3) . . ?
C15 C16 C17 179.6(3) . . ?
O2 C17 C16 109.90(18) . . ?
O2 C17 C18 107.84(19) . . ?
C16 C17 C18 112.3(2) . . ?
O2 C17 H17 108.9 . . ?
C16 C17 H17 108.9 . . ?
C18 C17 H17 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_150K
_database_code_depnum_ccdc_archive 'CCDC 1855849'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6883(4)
_cell_length_b                   7.4343(5)
_cell_length_c                   28.140(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1190.00(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3667
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.64

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12671
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.834
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2951
_reflns_number_gt                2301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999

_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-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0430P)²+0.0940P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2951
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.8980(4) 0.3658(3) 0.06793(8) 0.0410(6) Uani 1 1 d . . . . .
H1A H 0.965620 0.361833 0.035911 0.061 Uiso 1 1 calc R U . . .
H1B H 0.886683 0.243418 0.080643 0.061 Uiso 1 1 calc R U . . .
H1C H 0.998921 0.438483 0.088626 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6551(4) 0.4489(3) 0.06576(7) 0.0232(5) Uani 1 1 d . . . . .
H2 H 0.554249 0.372615 0.044776 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5466(4) 0.4564(3) 0.11313(7) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.4620(4) 0.4534(3) 0.15183(7) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.3567(4) 0.4434(2) 0.19844(7) 0.0195(4) Uani 1 1 d . . . . .
C6 C 0.1395(4) 0.3581(3) 0.20434(7) 0.0219(5) Uani 1 1 d . . . . .
H6 H 0.059557 0.310322 0.177528 0.026 Uiso 1 1 calc R U . . .
C7 C 0.0409(4) 0.3432(2) 0.24902(7) 0.0207(5) Uani 1 1 d . . . . .
H7 H -0.106322 0.284570 0.252729 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1552(4) 0.4134(2) 0.28874(7) 0.0185(4) Uani 1 1 d . . . . .
C9 C 0.3714(4) 0.4985(3) 0.28282(7) 0.0214(5) Uani 1 1 d . . . . .
H9 H 0.451267 0.546359 0.309635 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4704(4) 0.5136(3) 0.23814(7) 0.0203(5) Uani 1 1 d . . . . .
H10 H 0.617445 0.572543 0.234479 0.024 Uiso 1 1 calc R U . . .
C11 C 0.0459(4) 0.3969(3) 0.33463(7) 0.0218(5) Uani 1 1 d . . . . .
C12 C -0.0541(4) 0.3807(3) 0.37167(7) 0.0230(5) Uani 1 1 d . . . . .
C13 C -0.1769(4) 0.3584(3) 0.41740(7) 0.0221(5) Uani 1 1 d . . . . .
H13 H -0.245215 0.234556 0.418781 0.027 Uiso 1 1 calc R U . . .
C14 C -0.3720(4) 0.4935(3) 0.42416(8) 0.0294(5) Uani 1 1 d . . . . .
H14A H -0.444234 0.476009 0.455436 0.044 Uiso 1 1 calc R U . . .
H14B H -0.490929 0.476691 0.399355 0.044 Uiso 1 1 calc R U . . .
H14C H -0.307558 0.615475 0.422069 0.044 Uiso 1 1 calc R U . . .
O1 O 0.6654(3) 0.62650(18) 0.04596(5) 0.0240(4) Uani 1 1 d . . . . .
O2 O -0.0132(3) 0.3791(2) 0.45586(5) 0.0271(4) Uani 1 1 d . . . . .
H1 H 0.626(5) 0.624(3) 0.0173(10) 0.049(8) Uiso 1 1 d . . . . .
H2A H 0.108(5) 0.296(3) 0.4512(9) 0.060(9) 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
C1 C2 1.515(3) . ?
C2 O1 1.434(2) . ?
C2 C3 1.470(3) . ?
C3 C4 1.191(3) . ?
C4 C5 1.444(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.393(3) . ?
C8 C11 1.439(3) . ?
C9 C10 1.382(3) . ?
C11 C12 1.194(3) . ?
C12 C13 1.474(3) . ?
C13 O2 1.436(2) . ?
C13 C14 1.509(3) . ?

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 C2 C3 109.55(16) . . ?
O1 C2 C1 110.72(18) . . ?
C3 C2 C1 111.23(17) . . ?
C4 C3 C2 176.6(2) . . ?
C3 C4 C5 178.0(2) . . ?
C10 C5 C6 119.02(17) . . ?
C10 C5 C4 121.11(18) . . ?
C6 C5 C4 119.85(18) . . ?
C7 C6 C5 120.21(18) . . ?
C6 C7 C8 120.68(19) . . ?
C9 C8 C7 119.06(17) . . ?
C9 C8 C11 121.86(17) . . ?
C7 C8 C11 119.08(18) . . ?
C10 C9 C8 120.36(18) . . ?
C9 C10 C5 120.67(18) . . ?
C12 C11 C8 177.0(2) . . ?
C11 C12 C13 179.3(2) . . ?
O2 C13 C12 109.80(16) . . ?
O2 C13 C14 108.09(16) . . ?
C12 C13 C14 112.55(17) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_210K
_database_code_depnum_ccdc_archive 'CCDC 1855851'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6944(5)
_cell_length_b                   7.4936(6)
_cell_length_c                   28.143(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1200.89(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    3234
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      26.71

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13087
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.000
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2988
_reflns_number_gt                2051
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.995
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_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)+(0.0432P)²+0.0535P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C1 C 0.8928(5) 0.3647(4) 0.06724(10) 0.0590(8) Uani 1 1 d . . . . .
H1A H 0.958627 0.359755 0.035478 0.089 Uiso 1 1 calc R U . . .
H1B H 0.880289 0.244758 0.079966 0.089 Uiso 1 1 calc R U . . .
H1C H 0.994182 0.435505 0.087530 0.089 Uiso 1 1 calc R U . . .
C2 C 0.6521(4) 0.4488(3) 0.06530(8) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.551087 0.375067 0.044444 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5444(4) 0.4558(3) 0.11269(8) 0.0315(5) Uani 1 1 d . . . . .
C4 C 0.4606(4) 0.4526(3) 0.15134(8) 0.0308(6) Uani 1 1 d . . . . .
C5 C 0.3560(4) 0.4425(3) 0.19809(7) 0.0271(5) Uani 1 1 d . . . . .
C6 C 0.1401(4) 0.3579(3) 0.20424(8) 0.0315(5) Uani 1 1 d . . . . .
H6 H 0.060266 0.310614 0.177842 0.038 Uiso 1 1 calc R U . . .
C7 C 0.0435(4) 0.3434(3) 0.24898(8) 0.0285(5) Uani 1 1 d . . . . .
H7 H -0.101536 0.285342 0.252860 0.034 Uiso 1 1 calc R U . . .
C8 C 0.1575(4) 0.4134(3) 0.28839(7) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.3717(4) 0.4982(3) 0.28223(7) 0.0301(5) Uani 1 1 d . . . . .
H9 H 0.450955 0.545611 0.308676 0.036 Uiso 1 1 calc R U . . .
C10 C 0.4697(4) 0.5135(3) 0.23744(7) 0.0297(5) Uani 1 1 d . . . . .
H10 H 0.614270 0.572300 0.233615 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0487(4) 0.3972(3) 0.33438(8) 0.0313(6) Uani 1 1 d . . . . .
C12 C -0.0510(4) 0.3810(3) 0.37141(8) 0.0323(6) Uani 1 1 d . . . . .
C13 C -0.1737(4) 0.3585(3) 0.41706(8) 0.0315(5) Uani 1 1 d . . . . .
H13 H -0.242296 0.237188 0.418192 0.038 Uiso 1 1 calc R U . . .
C14 C -0.3674(4) 0.4927(3) 0.42376(9) 0.0425(6) Uani 1 1 d . . . . .
H14A H -0.439286 0.475532 0.454675 0.064 Uiso 1 1 calc R U . . .
H14B H -0.484785 0.476739 0.399149 0.064 Uiso 1 1 calc R U . . .
H14C H -0.303020 0.612296 0.421787 0.064 Uiso 1 1 calc R U . . .
O1 O 0.6640(3) 0.6251(2) 0.04585(6) 0.0342(4) Uani 1 1 d . . . . .
O2 O -0.0112(3) 0.3773(2) 0.45556(5) 0.0387(4) Uani 1 1 d . . . . .
H1 H 0.622(5) 0.625(4) 0.0185(10) 0.059(9) Uiso 1 1 d . . . . .
H2A H 0.106(6) 0.296(4) 0.4509(10) 0.069(10) 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
C1 C2 1.510(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O1 1.432(3) . ?
C2 C3 1.469(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.188(3) . ?
C4 C5 1.446(3) . ?
C5 C10 1.389(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.386(3) . ?
C8 C11 1.440(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.193(3) . ?
C12 C13 1.472(3) . ?
C13 O2 1.432(3) . ?
C13 C14 1.504(3) . ?
C13 H13 0.9900 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
O1 H1 0.80(3) . ?
O2 H2A 0.91(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.50(17) . . ?
O1 C2 C1 110.8(2) . . ?
C3 C2 C1 111.17(19) . . ?
O1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C4 C3 C2 176.6(2) . . ?
C3 C4 C5 178.1(2) . . ?
C10 C5 C6 119.09(19) . . ?
C10 C5 C4 120.9(2) . . ?
C6 C5 C4 120.0(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.01(19) . . ?
C9 C8 C11 121.97(19) . . ?
C7 C8 C11 119.0(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C8 176.8(2) . . ?
C11 C12 C13 179.3(2) . . ?
O2 C13 C12 110.02(18) . . ?
O2 C13 C14 108.26(18) . . ?
C12 C13 C14 112.38(19) . . ?
O2 C13 H13 108.7 . . ?
C12 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 110(2) . . ?
C13 O2 H2A 107.3(18) . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_240K
_database_code_depnum_ccdc_archive 'CCDC 1855852'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.6982(5)
_cell_length_b                   7.5247(6)
_cell_length_c                   28.143(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1206.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    2946
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.65

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13197
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.000
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3010
_reflns_number_gt                1885
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.995
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0445P)²+0.0283P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.8899(5) 0.3644(4) 0.06675(10) 0.0689(10) Uani 1 1 d . . . . .
H1A H 0.955286 0.359767 0.034954 0.103 Uiso 1 1 calc R U . . .
H1B H 0.876926 0.244831 0.079359 0.103 Uiso 1 1 calc R U . . .
H1C H 0.991751 0.434362 0.087066 0.103 Uiso 1 1 calc R U . . .
C2 C 0.6506(5) 0.4485(3) 0.06501(8) 0.0385(6) Uani 1 1 d . . . . .
H2 H 0.549062 0.375593 0.044162 0.046 Uiso 1 1 calc R U . . .
C3 C 0.5433(4) 0.4557(3) 0.11246(9) 0.0378(6) Uani 1 1 d . . . . .
C4 C 0.4594(4) 0.4524(3) 0.15113(9) 0.0370(6) Uani 1 1 d . . . . .
C5 C 0.3553(4) 0.4425(3) 0.19784(8) 0.0320(6) Uani 1 1 d . . . . .
C6 C 0.1410(5) 0.3580(3) 0.20408(8) 0.0372(6) Uani 1 1 d . . . . .
H6 H 0.061438 0.310539 0.177708 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0446(4) 0.3434(3) 0.24876(8) 0.0341(6) Uani 1 1 d . . . . .
H7 H -0.100034 0.284993 0.252620 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1578(4) 0.4137(3) 0.28820(8) 0.0306(6) Uani 1 1 d . . . . .
C9 C 0.3713(4) 0.4981(3) 0.28182(8) 0.0354(6) Uani 1 1 d . . . . .
H9 H 0.450528 0.545797 0.308204 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4689(4) 0.5130(3) 0.23723(8) 0.0348(6) Uani 1 1 d . . . . .
H10 H 0.613586 0.571320 0.233422 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0506(4) 0.3975(3) 0.33416(9) 0.0372(6) Uani 1 1 d . . . . .
C12 C -0.0489(4) 0.3809(3) 0.37112(9) 0.0375(6) Uani 1 1 d . . . . .
C13 C -0.1725(4) 0.3584(3) 0.41666(8) 0.0369(6) Uani 1 1 d . . . . .
H13 H -0.241662 0.237716 0.417693 0.044 Uiso 1 1 calc R U . . .
C14 C -0.3649(4) 0.4923(4) 0.42349(9) 0.0499(7) Uani 1 1 d . . . . .
H14A H -0.440528 0.472349 0.453906 0.075 Uiso 1 1 calc R U . . .
H14B H -0.479523 0.479932 0.398215 0.075 Uiso 1 1 calc R U . . .
H14C H -0.299031 0.611117 0.422753 0.075 Uiso 1 1 calc R U . . .
O1 O 0.6629(3) 0.6241(2) 0.04572(7) 0.0399(5) Uani 1 1 d . . . . .
O2 O -0.0103(3) 0.3764(2) 0.45530(6) 0.0457(5) Uani 1 1 d . . . . .
H1 H 0.619(6) 0.625(4) 0.0169(11) 0.084(12) Uiso 1 1 d . . . . .
H2A H 0.109(6) 0.297(4) 0.4510(10) 0.081(11) 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
C1 C2 1.504(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O1 1.430(3) . ?
C2 C3 1.470(3) . ?
C2 H2 0.9900 . ?
C3 C4 1.189(3) . ?
C4 C5 1.444(3) . ?
C5 C6 1.388(3) . ?
C5 C10 1.389(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.385(3) . ?
C8 C11 1.435(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.191(3) . ?
C12 C13 1.472(3) . ?
C13 O2 1.434(3) . ?
C13 C14 1.501(3) . ?
C13 H13 0.9900 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
O1 H1 0.85(3) . ?
O2 H2A 0.91(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.35(19) . . ?
O1 C2 C1 110.9(2) . . ?
C3 C2 C1 111.3(2) . . ?
O1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C4 C3 C2 176.6(2) . . ?
C3 C4 C5 178.2(2) . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 C4 120.0(2) . . ?
C10 C5 C4 121.0(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 C11 122.0(2) . . ?
C7 C8 C11 119.4(2) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C8 176.5(3) . . ?
C11 C12 C13 179.4(3) . . ?
O2 C13 C12 109.9(2) . . ?
O2 C13 C14 108.07(19) . . ?
C12 C13 C14 112.6(2) . . ?
O2 C13 H13 108.7 . . ?
C12 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 111(2) . . ?
C13 O2 H2A 108.4(19) . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_340K
_database_code_depnum_ccdc_archive 'CCDC 1855858'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7113(7)
_cell_length_b                   7.6398(9)
_cell_length_c                   28.117(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1226.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    340(2)
_cell_measurement_reflns_used    2150
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.80

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      340(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13183
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.763
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.000
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3055
_reflns_number_gt                1366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.998
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0440P)²+0.0568P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1785
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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
C1 C 0.8804(7) 0.3628(6) 0.06520(14) 0.1052(16) Uani 1 1 d . . . . .
H1A H 0.944711 0.359866 0.033666 0.158 Uiso 1 1 calc R U . . .
H1B H 0.864730 0.245467 0.077008 0.158 Uiso 1 1 calc R U . . .
H1C H 0.982777 0.427941 0.085692 0.158 Uiso 1 1 calc R U . . .
C2 C 0.6446(6) 0.4488(4) 0.06401(11) 0.0578(9) Uani 1 1 d . . . . .
H2 H 0.542138 0.379936 0.043236 0.069 Uiso 1 1 calc R U . . .
C3 C 0.5393(6) 0.4546(4) 0.11153(12) 0.0576(9) Uani 1 1 d . . . . .
C4 C 0.4565(6) 0.4507(4) 0.15010(12) 0.0569(9) Uani 1 1 d . . . . .
C5 C 0.3550(6) 0.4408(4) 0.19691(10) 0.0490(8) Uani 1 1 d . . . . .
C6 C 0.1435(6) 0.3569(4) 0.20348(11) 0.0566(9) Uani 1 1 d . . . . .
H6 H 0.064895 0.309812 0.177492 0.068 Uiso 1 1 calc R U . . .
C7 C 0.0482(6) 0.3425(4) 0.24830(11) 0.0535(9) Uani 1 1 d . . . . .
H7 H -0.093926 0.284968 0.252333 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1613(6) 0.4127(4) 0.28736(10) 0.0470(8) Uani 1 1 d . . . . .
C9 C 0.3709(6) 0.4972(4) 0.28062(11) 0.0566(9) Uani 1 1 d . . . . .
H9 H 0.448762 0.545356 0.306559 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4672(6) 0.5113(4) 0.23590(11) 0.0557(9) Uani 1 1 d . . . . .
H10 H 0.609297 0.568902 0.231936 0.067 Uiso 1 1 calc R U . . .
C11 C 0.0547(6) 0.3970(4) 0.33342(12) 0.0564(9) Uani 1 1 d . . . . .
C12 C -0.0421(6) 0.3801(4) 0.37042(12) 0.0585(9) Uani 1 1 d . . . . .
C13 C -0.1670(6) 0.3574(4) 0.41566(11) 0.0579(9) Uani 1 1 d . . . . .
H13 H -0.236543 0.240167 0.416360 0.069 Uiso 1 1 calc R U . . .
C14 C -0.3573(6) 0.4903(5) 0.42249(12) 0.0766(11) Uani 1 1 d . . . . .
H14A H -0.433199 0.470552 0.452478 0.115 Uiso 1 1 calc R U . . .
H14B H -0.469791 0.479684 0.397276 0.115 Uiso 1 1 calc R U . . .
H14C H -0.290824 0.605680 0.422077 0.115 Uiso 1 1 calc R U . . .
O1 O 0.6611(5) 0.6209(3) 0.04517(9) 0.0622(7) Uani 1 1 d . . . . .
O2 O -0.0069(5) 0.3734(3) 0.45440(8) 0.0699(8) Uani 1 1 d . . . . .
H1 H 0.611(7) 0.625(5) 0.0180(15) 0.114(18) Uiso 1 1 d . . . . .
H2A H 0.096(8) 0.291(5) 0.4480(14) 0.118(18) 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
C1 C2 1.499(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.421(4) . ?
C2 C3 1.466(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.183(4) . ?
C4 C5 1.440(4) . ?
C5 C10 1.379(4) . ?
C5 C6 1.380(4) . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(4) . ?
C8 C11 1.436(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.185(4) . ?
C12 C13 1.469(4) . ?
C13 O2 1.428(4) . ?
C13 C14 1.500(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.82(4) . ?
O2 H2A 0.88(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.8(3) . . ?
O1 C2 C1 110.8(3) . . ?
C3 C2 C1 111.2(3) . . ?
O1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C4 C3 C2 176.8(3) . . ?
C3 C4 C5 178.4(3) . . ?
C10 C5 C6 118.8(3) . . ?
C10 C5 C4 121.3(3) . . ?
C6 C5 C4 119.9(3) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 C11 122.2(3) . . ?
C7 C8 C11 119.1(3) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C8 176.9(4) . . ?
C11 C12 C13 178.6(4) . . ?
O2 C13 C12 109.8(3) . . ?
O2 C13 C14 108.0(3) . . ?
C12 C13 C14 112.5(3) . . ?
O2 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 111(3) . . ?
C13 O2 H2A 102(3) . . ?

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.030

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_330K
_database_code_depnum_ccdc_archive 'CCDC 1855857'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7113(7)
_cell_length_b                   7.6271(8)
_cell_length_c                   28.122(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1225.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    330(2)
_cell_measurement_reflns_used    2223
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.80

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      330(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13167
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         28.367
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3066
_reflns_number_gt                1446
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.994
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0430P)²+0.0115P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1677
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.8829(6) 0.3625(5) 0.06545(12) 0.1020(14) Uani 1 1 d . . . . .
H1A H 0.946819 0.358634 0.033900 0.153 Uiso 1 1 calc R U . . .
H1B H 0.868054 0.245329 0.077573 0.153 Uiso 1 1 calc R U . . .
H1C H 0.985097 0.428806 0.085716 0.153 Uiso 1 1 calc R U . . .
C2 C 0.6449(6) 0.4484(4) 0.06415(10) 0.0560(8) Uani 1 1 d . . . . .
H2 H 0.542753 0.378997 0.043408 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5395(5) 0.4548(4) 0.11164(11) 0.0554(9) Uani 1 1 d . . . . .
C4 C 0.4572(5) 0.4508(4) 0.15018(11) 0.0551(9) Uani 1 1 d . . . . .
C5 C 0.3549(5) 0.4406(4) 0.19697(10) 0.0472(7) Uani 1 1 d . . . . .
C6 C 0.1429(6) 0.3572(4) 0.20380(10) 0.0549(8) Uani 1 1 d . . . . .
H6 H 0.063687 0.310129 0.177880 0.066 Uiso 1 1 calc R U . . .
C7 C 0.0483(5) 0.3432(4) 0.24838(11) 0.0522(8) Uani 1 1 d . . . . .
H7 H -0.093884 0.285566 0.252383 0.063 Uiso 1 1 calc R U . . .
C8 C 0.1606(5) 0.4132(3) 0.28745(10) 0.0448(7) Uani 1 1 d . . . . .
C9 C 0.3713(5) 0.4974(4) 0.28074(10) 0.0547(8) Uani 1 1 d . . . . .
H9 H 0.449286 0.545185 0.306714 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4680(5) 0.5118(4) 0.23597(10) 0.0527(8) Uani 1 1 d . . . . .
H10 H 0.610037 0.569638 0.231968 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0541(5) 0.3970(4) 0.33356(11) 0.0531(8) Uani 1 1 d . . . . .
C12 C -0.0423(5) 0.3800(4) 0.37054(11) 0.0559(9) Uani 1 1 d . . . . .
C13 C -0.1673(5) 0.3579(4) 0.41563(10) 0.0546(8) Uani 1 1 d . . . . .
H13 H -0.236465 0.240343 0.416311 0.066 Uiso 1 1 calc R U . . .
C14 C -0.3588(5) 0.4901(5) 0.42258(11) 0.0752(10) Uani 1 1 d . . . . .
H14A H -0.435926 0.468611 0.452344 0.113 Uiso 1 1 calc R U . . .
H14B H -0.469992 0.480434 0.397123 0.113 Uiso 1 1 calc R U . . .
H14C H -0.292904 0.605923 0.422731 0.113 Uiso 1 1 calc R U . . .
O1 O 0.6608(4) 0.6211(3) 0.04526(8) 0.0601(6) Uani 1 1 d . . . . .
O2 O -0.0073(4) 0.3735(3) 0.45451(7) 0.0673(7) Uani 1 1 d . . . . .
H2A H 0.108(7) 0.291(5) 0.4494(13) 0.125(17) Uiso 1 1 d . . . . .
H1 H 0.621(7) 0.626(5) 0.0166(13) 0.106(15) 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
C1 C2 1.509(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.424(3) . ?
C2 C3 1.466(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.182(4) . ?
C4 C5 1.442(4) . ?
C5 C6 1.381(4) . ?
C5 C10 1.384(3) . ?
C6 C7 1.369(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(4) . ?
C8 C11 1.438(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.183(4) . ?
C12 C13 1.465(4) . ?
C13 O2 1.430(3) . ?
C13 C14 1.500(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 H1 0.84(4) . ?
O2 H2A 0.92(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.6(2) . . ?
O1 C2 C1 110.7(3) . . ?
C3 C2 C1 111.2(3) . . ?
O1 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
C4 C3 C2 176.5(3) . . ?
C3 C4 C5 178.3(3) . . ?
C6 C5 C10 118.7(3) . . ?
C6 C5 C4 120.5(3) . . ?
C10 C5 C4 120.8(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.5(3) . . ?
C9 C8 C11 122.2(3) . . ?
C7 C8 C11 119.2(3) . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C8 176.9(3) . . ?
C11 C12 C13 178.5(3) . . ?
O2 C13 C12 109.9(2) . . ?
O2 C13 C14 108.1(2) . . ?
C12 C13 C14 113.0(3) . . ?
O2 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 O1 H1 112(3) . . ?
C13 O2 H2A 106(2) . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_350K
_database_code_depnum_ccdc_archive 'CCDC 1855859'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7130(8)
_cell_length_b                   7.6527(9)
_cell_length_c                   28.116(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1229.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    2046
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.47

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13248
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3073
_reflns_number_gt                1324
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.994
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0428P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1840
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
C1 C 0.8798(7) 0.3622(5) 0.06497(13) 0.1120(15) Uani 1 1 d . . . . .
H1A H 0.944006 0.359599 0.033422 0.168 Uiso 1 1 calc R U . . .
H1B H 0.863759 0.244892 0.076645 0.168 Uiso 1 1 calc R U . . .
H1C H 0.982523 0.426661 0.085522 0.168 Uiso 1 1 calc R U . . .
C2 C 0.6439(6) 0.4488(4) 0.06391(10) 0.0611(9) Uani 1 1 d . . . . .
H2 H 0.541166 0.380260 0.043146 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5385(5) 0.4548(4) 0.11130(11) 0.0606(9) Uani 1 1 d . . . . .
C4 C 0.4570(6) 0.4503(4) 0.14991(11) 0.0604(9) Uani 1 1 d . . . . .
C5 C 0.3545(6) 0.4403(4) 0.19676(10) 0.0518(8) Uani 1 1 d . . . . .
C6 C 0.1437(6) 0.3571(4) 0.20340(11) 0.0611(9) Uani 1 1 d . . . . .
H6 H 0.064532 0.310341 0.177445 0.073 Uiso 1 1 calc R U . . .
C7 C 0.0494(6) 0.3426(4) 0.24819(11) 0.0561(9) Uani 1 1 d . . . . .
H7 H -0.092352 0.284666 0.252185 0.067 Uiso 1 1 calc R U . . .
C8 C 0.1607(5) 0.4122(4) 0.28725(10) 0.0493(8) Uani 1 1 d . . . . .
C9 C 0.3716(5) 0.4968(4) 0.28049(10) 0.0595(9) Uani 1 1 d . . . . .
H9 H 0.449754 0.544484 0.306437 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4674(6) 0.5111(4) 0.23570(11) 0.0578(8) Uani 1 1 d . . . . .
H10 H 0.609255 0.568869 0.231639 0.069 Uiso 1 1 calc R U . . .
C11 C 0.0556(6) 0.3972(4) 0.33330(12) 0.0599(9) Uani 1 1 d . . . . .
C12 C -0.0405(6) 0.3801(4) 0.37036(11) 0.0607(9) Uani 1 1 d . . . . .
C13 C -0.1660(6) 0.3574(4) 0.41552(10) 0.0607(9) Uani 1 1 d . . . . .
H13 H -0.235580 0.240409 0.416176 0.073 Uiso 1 1 calc R U . . .
C14 C -0.3564(6) 0.4901(5) 0.42216(11) 0.0815(11) Uani 1 1 d . . . . .
H14A H -0.434341 0.469453 0.451879 0.122 Uiso 1 1 calc R U . . .
H14B H -0.467045 0.480676 0.396604 0.122 Uiso 1 1 calc R U . . .
H14C H -0.289531 0.605239 0.422263 0.122 Uiso 1 1 calc R U . . .
O1 O 0.6604(4) 0.6208(3) 0.04508(9) 0.0657(7) Uani 1 1 d . . . . .
O2 O -0.0066(5) 0.3733(3) 0.45428(8) 0.0744(8) Uani 1 1 d . . . . .
H1 H 0.614(6) 0.625(5) 0.0172(13) 0.106(16) Uiso 1 1 d . . . . .
H2A H 0.102(7) 0.294(4) 0.4485(13) 0.106(16) 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
C1 C2 1.502(5) . ?
C2 O1 1.422(3) . ?
C2 C3 1.463(4) . ?
C3 C4 1.182(4) . ?
C4 C5 1.443(4) . ?
C5 C6 1.375(4) . ?
C5 C10 1.382(4) . ?
C6 C7 1.374(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.381(4) . ?
C8 C11 1.432(4) . ?
C9 C10 1.378(4) . ?
C11 C12 1.185(4) . ?
C12 C13 1.469(4) . ?
C13 O2 1.425(4) . ?
C13 C14 1.500(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
O1 C2 C3 109.7(2) . . ?
O1 C2 C1 110.9(3) . . ?
C3 C2 C1 111.4(3) . . ?
C4 C3 C2 176.3(3) . . ?
C3 C4 C5 178.5(3) . . ?
C6 C5 C10 118.9(3) . . ?
C6 C5 C4 120.2(3) . . ?
C10 C5 C4 120.8(3) . . ?
C7 C6 C5 120.3(3) . . ?
C6 C7 C8 121.3(3) . . ?
C7 C8 C9 118.3(3) . . ?
C7 C8 C11 119.8(3) . . ?
C9 C8 C11 121.9(3) . . ?
C10 C9 C8 120.7(3) . . ?
C9 C10 C5 120.5(3) . . ?
C12 C11 C8 176.6(4) . . ?
C11 C12 C13 178.3(4) . . ?
O2 C13 C12 109.8(3) . . ?
O2 C13 C14 108.1(2) . . ?
C12 C13 C14 112.5(3) . . ?

_refine_diff_density_max         0.107
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.029

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_270K
_database_code_depnum_ccdc_archive 'CCDC 1855853'
_audit_update_record             
;
2018-07-14 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          397.32
_chemical_formula_moiety         'C14 H14 O2'
_chemical_formula_sum            'C14 H14 O2'
_chemical_formula_weight         214.25

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.7057(5)
_cell_length_b                   7.5595(6)
_cell_length_c                   28.152(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1214.24(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    2725
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      26.57

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13376
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.790
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3030
_reflns_number_gt                1746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.998
_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 APEX-III'
_computing_cell_refinement       'Bruker APEX-III'
_computing_data_reduction        'Bruker SAINT '
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_publication_material  ?
_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)+(0.0409P)²+0.0609P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
C1 C 0.8877(6) 0.3638(4) 0.06635(11) 0.0794(11) Uani 1 1 d . . . . .
H1A H 0.952246 0.360303 0.034869 0.119 Uiso 1 1 calc R U . . .
H1B H 0.874161 0.245486 0.078458 0.119 Uiso 1 1 calc R U . . .
H1C H 0.988923 0.431422 0.086648 0.119 Uiso 1 1 calc R U . . .
C2 C 0.6487(5) 0.4487(3) 0.06489(9) 0.0439(7) Uani 1 1 d . . . . .
H2 H 0.547655 0.377444 0.044242 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5420(5) 0.4555(3) 0.11220(9) 0.0427(7) Uani 1 1 d . . . . .
C4 C 0.4590(5) 0.4515(3) 0.15081(9) 0.0425(7) Uani 1 1 d . . . . .
C5 C 0.3552(5) 0.4418(3) 0.19756(8) 0.0364(6) Uani 1 1 d . . . . .
C6 C 0.1415(5) 0.3575(3) 0.20410(9) 0.0424(7) Uani 1 1 d . . . . .
H6 H 0.062543 0.310405 0.178112 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0458(5) 0.3433(3) 0.24873(9) 0.0390(7) Uani 1 1 d . . . . .
H7 H -0.097054 0.285864 0.252604 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1583(5) 0.4130(3) 0.28792(8) 0.0350(6) Uani 1 1 d . . . . .
C9 C 0.3714(5) 0.4981(3) 0.28154(9) 0.0414(7) Uani 1 1 d . . . . .
H9 H 0.449377 0.545642 0.307582 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4684(5) 0.5126(3) 0.23685(9) 0.0403(7) Uani 1 1 d . . . . .
H10 H 0.611060 0.570321 0.232988 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0512(5) 0.3975(3) 0.33397(10) 0.0424(7) Uani 1 1 d . . . . .
C12 C -0.0467(5) 0.3805(3) 0.37092(9) 0.0433(7) Uani 1 1 d . . . . .
C13 C -0.1706(5) 0.3581(3) 0.41635(9) 0.0422(7) Uani 1 1 d . . . . .
H13 H -0.239010 0.239281 0.417281 0.051 Uiso 1 1 calc R U . . .
C14 C -0.3631(5) 0.4913(4) 0.42323(10) 0.0574(8) Uani 1 1 d . . . . .
H14A H -0.438784 0.470755 0.453179 0.086 Uiso 1 1 calc R U . . .
H14B H -0.475574 0.479919 0.398049 0.086 Uiso 1 1 calc R U . . .
H14C H -0.297972 0.608409 0.422845 0.086 Uiso 1 1 calc R U . . .
O1 O 0.6625(4) 0.6233(2) 0.04558(7) 0.0461(5) Uani 1 1 d . . . . .
O2 O -0.0093(4) 0.3755(3) 0.45503(6) 0.0524(6) Uani 1 1 d . . . . .
H1 H 0.614(6) 0.623(4) 0.0173(12) 0.083(12) Uiso 1 1 d . . . . .
H2A H 0.107(6) 0.296(4) 0.4494(11) 0.090(13) 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
C1 C2 1.508(4) . ?
C2 O1 1.429(3) . ?
C2 C3 1.465(4) . ?
C3 C4 1.186(3) . ?
C4 C5 1.445(3) . ?
C5 C10 1.388(3) . ?
C5 C6 1.388(4) . ?
C6 C7 1.374(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.387(3) . ?
C8 C11 1.438(4) . ?
C9 C10 1.379(3) . ?
C11 C12 1.188(3) . ?
C12 C13 1.471(4) . ?
C13 O2 1.432(3) . ?
C13 C14 1.502(3) . ?

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 C2 C3 109.6(2) . . ?
O1 C2 C1 110.7(2) . . ?
C3 C2 C1 111.5(2) . . ?
C4 C3 C2 176.4(3) . . ?
C3 C4 C5 178.4(3) . . ?
C10 C5 C6 118.7(2) . . ?
C10 C5 C4 121.0(2) . . ?
C6 C5 C4 120.3(2) . . ?
C7 C6 C5 120.4(2) . . ?
C6 C7 C8 121.1(2) . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 C11 119.4(2) . . ?
C9 C8 C11 121.8(2) . . ?
C10 C9 C8 120.5(2) . . ?
C9 C10 C5 120.6(2) . . ?
C12 C11 C8 176.7(3) . . ?
C11 C12 C13 179.2(3) . . ?
O2 C13 C12 110.0(2) . . ?
O2 C13 C14 108.1(2) . . ?
C12 C13 C14 112.7(2) . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.034

