# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ga_90423a_a
_database_code_depnum_ccdc_archive 'CCDC 1951717'
loop_
_audit_author_name
_audit_author_address
zhp
;Tongji University
China
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2020-03-12 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         ?
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0389 0.0241 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4235(5)
_cell_length_b                   10.6627(7)
_cell_length_c                   12.6898(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1139.76(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      58.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.420
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19374
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.484
_diffrn_reflns_theta_max         58.095
_diffrn_reflns_theta_full        53.594
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2419
_reflns_number_gt                2332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component perfect inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as a perfect inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2419
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.65007(13) 0.39832(10) 0.35463(10) 0.0400(3) Uani 1 1 d . . . . .
H1 H 0.607(3) 0.378(2) 0.2988(18) 0.057(6) Uiso 1 1 d . . . . .
O2 O 0.44517(15) 0.82097(10) 0.35297(9) 0.0452(3) Uani 1 1 d . . . . .
C1 C 0.56077(16) 0.49882(13) 0.40078(11) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.63667(19) 0.51949(15) 0.50835(12) 0.0376(3) Uani 1 1 d . . . . .
H2A H 0.618442 0.446073 0.551830 0.045 Uiso 1 1 calc R U . . .
H2B H 0.750424 0.528982 0.499549 0.045 Uiso 1 1 calc R U . . .
C3 C 0.5717(2) 0.63402(16) 0.56436(12) 0.0412(4) Uani 1 1 d . . . . .
H3A H 0.624774 0.644059 0.631685 0.049 Uiso 1 1 calc R U . . .
H3B H 0.459186 0.622970 0.577559 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5977(2) 0.75059(16) 0.49736(14) 0.0435(4) Uani 1 1 d . . . . .
H4A H 0.551217 0.822504 0.532598 0.052 Uiso 1 1 calc R U . . .
H4B H 0.710666 0.765751 0.490053 0.052 Uiso 1 1 calc R U . . .
C5 C 0.52477(17) 0.73693(14) 0.38987(11) 0.0320(3) Uani 1 1 d . . . . .
C6 C 0.56009(17) 0.61748(13) 0.32689(10) 0.0312(3) Uani 1 1 d . . . . .
C7 C 0.4218(2) 0.59070(14) 0.25022(11) 0.0372(3) Uani 1 1 d . . . . .
H7A H 0.373110 0.668006 0.226151 0.045 Uiso 1 1 calc R U . . .
H7B H 0.457823 0.543153 0.189605 0.045 Uiso 1 1 calc R U . . .
C8 C 0.30834(18) 0.51543(13) 0.31591(11) 0.0337(3) Uani 1 1 d . . . . .
C9 C 0.1481(2) 0.49097(16) 0.29981(14) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.095773 0.524459 0.241725 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0671(2) 0.41644(18) 0.37089(15) 0.0510(4) Uani 1 1 d . . . . .
H10 H -0.040154 0.399956 0.360455 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1441(2) 0.36612(18) 0.45738(15) 0.0494(4) Uani 1 1 d . . . . .
H11 H 0.088224 0.316203 0.504668 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3045(2) 0.38969(15) 0.47407(12) 0.0404(3) Uani 1 1 d . . . . .
H12 H 0.356570 0.355533 0.531962 0.048 Uiso 1 1 calc R U . . .
C13 C 0.38540(16) 0.46485(13) 0.40308(11) 0.0308(3) Uani 1 1 d . . . . .
C14 C 0.7197(2) 0.64007(18) 0.27128(15) 0.0477(4) Uani 1 1 d . . . . .
H14A H 0.711283 0.712244 0.226405 0.072 Uiso 1 1 calc R U . . .
H14B H 0.746580 0.567941 0.229664 0.072 Uiso 1 1 calc R U . . .
H14C H 0.800878 0.654115 0.323043 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4342(17) . ?
O1 H1 0.82(2) . ?
O2 C5 1.2132(19) . ?
C1 C13 1.5213(19) . ?
C1 C2 1.5234(19) . ?
C1 C6 1.5748(19) . ?
C2 C3 1.515(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.503(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5328(19) . ?
C6 C14 1.537(2) . ?
C6 C7 1.544(2) . ?
C7 C8 1.501(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.390(2) . ?
C8 C13 1.391(2) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C1 O1 H1 108.4(16) . . ?
O1 C1 C13 109.83(11) . . ?
O1 C1 C2 104.71(11) . . ?
C13 C1 C2 115.13(12) . . ?
O1 C1 C6 111.04(11) . . ?
C13 C1 C6 101.49(11) . . ?
C2 C1 C6 114.76(12) . . ?
C3 C2 C1 112.68(13) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 110.15(13) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.67(13) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 C4 120.30(14) . . ?
O2 C5 C6 121.32(13) . . ?
C4 C5 C6 118.33(13) . . ?
C5 C6 C14 106.19(13) . . ?
C5 C6 C7 109.62(12) . . ?
C14 C6 C7 113.54(12) . . ?
C5 C6 C1 110.97(10) . . ?
C14 C6 C1 113.32(12) . . ?
C7 C6 C1 103.26(11) . . ?
C8 C7 C6 103.26(11) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C13 119.81(15) . . ?
C9 C8 C7 129.58(15) . . ?
C13 C8 C7 110.60(13) . . ?
C10 C9 C8 119.42(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.64(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.42(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.93(16) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 120.78(14) . . ?
C12 C13 C1 128.92(13) . . ?
C8 C13 C1 110.21(13) . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 172.67(12) . . . . ?
C13 C1 C2 C3 -66.63(17) . . . . ?
C6 C1 C2 C3 50.67(17) . . . . ?
C1 C2 C3 C4 -58.31(18) . . . . ?
C2 C3 C4 C5 56.33(19) . . . . ?
C3 C4 C5 O2 133.60(16) . . . . ?
C3 C4 C5 C6 -49.2(2) . . . . ?
O2 C5 C6 C14 93.18(17) . . . . ?
C4 C5 C6 C14 -84.02(16) . . . . ?
O2 C5 C6 C7 -29.84(19) . . . . ?
C4 C5 C6 C7 152.95(13) . . . . ?
O2 C5 C6 C1 -143.25(14) . . . . ?
C4 C5 C6 C1 39.55(18) . . . . ?
O1 C1 C6 C5 -157.82(11) . . . . ?
C13 C1 C6 C5 85.49(13) . . . . ?
C2 C1 C6 C5 -39.33(16) . . . . ?
O1 C1 C6 C14 -38.45(16) . . . . ?
C13 C1 C6 C14 -155.13(13) . . . . ?
C2 C1 C6 C14 80.04(16) . . . . ?
O1 C1 C6 C7 84.81(13) . . . . ?
C13 C1 C6 C7 -31.87(13) . . . . ?
C2 C1 C6 C7 -156.69(12) . . . . ?
C5 C6 C7 C8 -87.14(13) . . . . ?
C14 C6 C7 C8 154.29(13) . . . . ?
C1 C6 C7 C8 31.17(14) . . . . ?
C6 C7 C8 C9 162.06(15) . . . . ?
C6 C7 C8 C13 -18.95(16) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C10 178.91(15) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C11 C12 C13 C1 -176.59(15) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?
C7 C8 C13 C12 -178.80(13) . . . . ?
C9 C8 C13 C1 177.07(13) . . . . ?
C7 C8 C13 C1 -2.03(16) . . . . ?
O1 C1 C13 C12 80.43(18) . . . . ?
C2 C1 C13 C12 -37.4(2) . . . . ?
C6 C1 C13 C12 -162.01(15) . . . . ?
O1 C1 C13 C8 -96.01(13) . . . . ?
C2 C1 C13 C8 146.13(13) . . . . ?
C6 C1 C13 C8 21.56(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82(2) 2.07(2) 2.8747(17) 166(2) 3_645

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028



