# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_G210429A
_database_code_depnum_ccdc_archive 'CCDC 2108994'
loop_
_audit_author_name
_audit_author_address
'Hong-Xi Li'
;Soochow University
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-21 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         'C14 H12 O2'
_chemical_formula_sum            'C14 H12 O2'
_chemical_formula_weight         212.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.8356(3)
_cell_length_b                   22.7724(11)
_cell_length_c                   7.0408(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.861(5)
_cell_angle_gamma                90
_cell_volume                     1072.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      6.5860
_cell_measurement_theta_max      76.8340

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.699
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5464
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.882
_diffrn_reflns_theta_max         77.554
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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             2265
_reflns_number_gt                1751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.1000P)²+0.1917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2265
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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 0.1915(3) 1.04797(7) -0.2358(2) 0.0457(4) Uani 1 1 d . . . . .
O2 O -0.0292(3) 0.87308(8) 0.5314(3) 0.0509(5) Uani 1 1 d . . . . .
H2 H -0.034703 0.897226 0.442172 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2843(3) 0.90872(9) 0.3269(3) 0.0335(4) Uani 1 1 d . . . . .
C3 C 0.2541(3) 1.00576(9) 0.0760(3) 0.0340(4) Uani 1 1 d . . . . .
C9 C 0.3014(3) 0.85765(9) 0.4619(3) 0.0361(4) Uani 1 1 d . . . . .
C2 C 0.2280(3) 1.05649(9) -0.0608(3) 0.0378(5) Uani 1 1 d . . . . .
C5 C 0.2798(3) 0.90093(9) 0.1287(3) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.288995 0.862883 0.079476 0.046 Uiso 1 1 calc R U . . .
C7 C 0.2753(3) 0.96541(9) 0.3969(3) 0.0383(5) Uani 1 1 d . . . . .
H7 H 0.278152 0.971268 0.529560 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2620(3) 0.94866(10) 0.0046(3) 0.0386(5) Uani 1 1 d . . . . .
H4 H 0.255219 0.942662 -0.128697 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2620(3) 1.01344(9) 0.2746(3) 0.0378(4) Uani 1 1 d . . . . .
H8 H 0.258358 1.051518 0.325255 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1482(3) 0.84402(9) 0.5597(3) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.4746(3) 0.82290(11) 0.4981(4) 0.0458(5) Uani 1 1 d . . . . .
H10 H 0.577049 0.830651 0.430706 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3462(4) 0.76516(10) 0.7291(3) 0.0491(6) Uani 1 1 d . . . . .
H12 H 0.362078 0.734562 0.820579 0.059 Uiso 1 1 calc R U . . .
C1 C 0.2465(4) 1.11753(10) 0.0205(4) 0.0491(5) Uani 1 1 d . . . . .
H1A H 0.221380 1.145710 -0.085012 0.074 Uiso 1 1 calc R U . . .
H1B H 0.380288 1.123300 0.096912 0.074 Uiso 1 1 calc R U . . .
H1C H 0.149756 1.123091 0.102266 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1705(4) 0.79797(10) 0.6928(3) 0.0450(5) Uani 1 1 d . . . . .
H13 H 0.067201 0.789072 0.757946 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4972(4) 0.77735(11) 0.6314(4) 0.0534(6) Uani 1 1 d . . . . .
H11 H 0.614891 0.754814 0.655166 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.222(3) . ?
O2 C14 1.360(3) . ?
O2 H2 0.8300 . ?
C6 C7 1.388(3) . ?
C6 C5 1.400(3) . ?
C6 C9 1.492(3) . ?
C3 C8 1.399(3) . ?
C3 C4 1.399(3) . ?
C3 C2 1.491(3) . ?
C9 C14 1.401(3) . ?
C9 C10 1.403(3) . ?
C2 C1 1.499(3) . ?
C5 C4 1.384(3) . ?
C5 H5 0.9400 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9400 . ?
C4 H4 0.9400 . ?
C8 H8 0.9400 . ?
C14 C13 1.394(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9400 . ?
C12 C11 1.381(4) . ?
C12 C13 1.392(4) . ?
C12 H12 0.9400 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C13 H13 0.9400 . ?
C11 H11 0.9400 . ?

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
C14 O2 H2 109.5 . . ?
C7 C6 C5 118.57(18) . . ?
C7 C6 C9 120.15(17) . . ?
C5 C6 C9 121.28(18) . . ?
C8 C3 C4 118.63(18) . . ?
C8 C3 C2 121.57(18) . . ?
C4 C3 C2 119.74(18) . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C6 121.18(18) . . ?
C10 C9 C6 120.51(19) . . ?
O1 C2 C3 120.07(19) . . ?
O1 C2 C1 121.1(2) . . ?
C3 C2 C1 118.84(18) . . ?
C4 C5 C6 120.70(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C8 C7 C6 121.09(18) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C5 C4 C3 120.50(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C7 C8 C3 120.48(19) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
O2 C14 C13 115.84(19) . . ?
O2 C14 C9 123.66(19) . . ?
C13 C14 C9 120.5(2) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
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 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.063

