# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_sq255-4
_database_code_depnum_ccdc_archive 'CCDC 2058379'
loop_
_audit_author_name
_audit_author_address
'Hao Wang'
;Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-01-25 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_audit_creation_date             2020-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 O3'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.843(11)
_cell_length_b                   5.480(2)
_cell_length_c                   15.129(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.15(2)
_cell_angle_gamma                90
_cell_volume                     1302.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1101
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.581
_cell_measurement_theta_min      2.593
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1058 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8739. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1573
_reflns_number_total             2261
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0997
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+5.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2488
_refine_ls_wR_factor_ref         0.2709
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H17(0.029) H9(0.031) H16(0.034) H7(0.036) H6(0.039) H14(0.037)
 H13(0.029) H4A(0.059) H4B(0.059) H4C(0.059) H5(0.042) H10A(0.028) H10B(0.028)
 H15(0.035)
 Fixed X: H17(0.497047) H9(0.231) H16(0.638702) H7(0.219207) H6(0.133804)
 H14(0.643977) H13(0.500872) H4A(-0.000498) H4B(0.032905) H4C(0.086352)
 H5(0.060969) H10A(0.358804) H10B(0.361263) H15(0.711022)
 Fixed Y: H17(-0.296582) H9(-0.015001) H16(-0.234438) H7(0.282958)
 H6(0.611001) H14(0.404662) H13(0.353295) H4A(0.733497) H4B(0.975645)
 H4C(0.858807) H5(0.852221) H10A(0.192262) H10B(0.343282) H15(0.115463)
 Fixed Z: H17(0.689927) H9(0.43888) H16(0.790329) H7(0.271786) H6(0.190559)
 H14(0.658109) H13(0.561856) H4A(0.434493) H4B(0.400015) H4C(0.500981)
 H5(0.263369) H10A(0.434311) H10B(0.525859) H15(0.774659)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2273(3) 0.1985(8) 0.5478(3) 0.0303(10) Uani 1 1 d . . . . .
O1 O 0.3599(3) -0.2165(7) 0.5572(3) 0.0328(11) Uani 1 1 d . . . . .
O3 O 0.1491(3) 0.4615(9) 0.5964(3) 0.0407(12) Uani 1 1 d . . . . .
C2 C 0.1514(3) 0.4779(11) 0.4358(4) 0.0250(13) Uani 1 1 d . . . . .
C8 C 0.1958(3) 0.3394(10) 0.3938(4) 0.0241(13) Uani 1 1 d . . . . .
C17 C 0.5263(4) -0.1528(10) 0.6841(4) 0.0245(13) Uani 1 1 d . . . . .
H17 H 0.497047 -0.296582 0.689927 0.029 Uiso 1 1 calc R . . . .
C9 C 0.2482(4) 0.1539(11) 0.4634(4) 0.0258(13) Uani 1 1 d . . . . .
H9 H 0.231000 -0.015001 0.438880 0.031 Uiso 1 1 calc R . . . .
C1 C 0.1728(4) 0.3902(11) 0.5335(4) 0.0271(13) Uani 1 1 d . . . . .
C11 C 0.3930(4) -0.0194(10) 0.5552(4) 0.0210(12) Uani 1 1 d . . . . .
C12 C 0.4846(3) 0.0226(10) 0.6159(4) 0.0207(12) Uani 1 1 d . . . . .
C16 C 0.6107(4) -0.1165(11) 0.7434(4) 0.0287(14) Uani 1 1 d . . . . .
H16 H 0.638702 -0.234438 0.790329 0.034 Uiso 1 1 calc R . . . .
C3 C 0.0984(4) 0.6715(11) 0.3906(4) 0.0271(13) Uani 1 1 d . . . . .
C7 C 0.1898(4) 0.3819(12) 0.3015(4) 0.0302(14) Uani 1 1 d . . . . .
H7 H 0.219207 0.282958 0.271786 0.036 Uiso 1 1 calc R . . . .
C6 C 0.1387(4) 0.5756(12) 0.2538(4) 0.0328(15) Uani 1 1 d . . . . .
H6 H 0.133804 0.611001 0.190559 0.039 Uiso 1 1 calc R . . . .
C14 C 0.6136(4) 0.2647(11) 0.6654(4) 0.0307(14) Uani 1 1 d . . . . .
H14 H 0.643977 0.404662 0.658109 0.037 Uiso 1 1 calc R . . . .
C13 C 0.5289(3) 0.2324(11) 0.6074(4) 0.0240(13) Uani 1 1 d . . . . .
H13 H 0.500872 0.353295 0.561856 0.029 Uiso 1 1 calc R . . . .
C4 C 0.0502(4) 0.8227(13) 0.4353(5) 0.0395(17) Uani 1 1 d . . . . .
H4A H -0.000498 0.733497 0.434493 0.059 Uiso 1 1 calc GR . . . .
H4B H 0.032905 0.975645 0.400015 0.059 Uiso 1 1 calc GR . . . .
H4C H 0.086352 0.858807 0.500981 0.059 Uiso 1 1 calc GR . . . .
C5 C 0.0944(4) 0.7194(12) 0.2974(4) 0.0351(16) Uani 1 1 d . . . . .
H5 H 0.060969 0.852221 0.263369 0.042 Uiso 1 1 calc R . . . .
C10 C 0.3441(4) 0.1862(10) 0.4920(4) 0.0235(13) Uani 1 1 d . . . . .
H10A H 0.358804 0.192262 0.434311 0.028 Uiso 1 1 calc R . . . .
H10B H 0.361263 0.343282 0.525859 0.028 Uiso 1 1 calc R . . . .
C15 C 0.6536(4) 0.0912(11) 0.7339(4) 0.0293(14) Uani 1 1 d . . . . .
H15 H 0.711022 0.115463 0.774659 0.035 Uiso 1 1 calc R . . . .


_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
O2 C9 1.464(7) . ?
O2 C1 1.360(7) . ?
O1 C11 1.221(7) . ?
O3 C1 1.220(7) . ?
C2 C8 1.373(8) . ?
C2 C1 1.471(8) . ?
C2 C3 1.396(8) . ?
C8 C9 1.500(8) . ?
C8 C7 1.383(8) . ?
C17 H17 0.9500 . ?
C17 C12 1.399(8) . ?
C17 C16 1.395(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.524(8) . ?
C11 C12 1.501(8) . ?
C11 C10 1.514(8) . ?
C12 C13 1.401(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.384(9) . ?
C3 C4 1.483(9) . ?
C3 C5 1.412(9) . ?
C7 H7 0.9500 . ?
C7 C6 1.392(9) . ?
C6 H6 0.9500 . ?
C6 C5 1.403(9) . ?
C14 H14 0.9500 . ?
C14 C13 1.390(8) . ?
C14 C15 1.388(9) . ?
C13 H13 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C9 110.6(4) . . ?
C8 C2 C1 107.9(5) . . ?
C8 C2 C3 123.6(5) . . ?
C3 C2 C1 128.5(6) . . ?
C2 C8 C9 109.3(5) . . ?
C2 C8 C7 121.4(5) . . ?
C7 C8 C9 129.3(5) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C12 120.0(5) . . ?
O2 C9 C8 103.5(5) . . ?
O2 C9 H9 110.4 . . ?
O2 C9 C10 107.3(4) . . ?
C8 C9 H9 110.4 . . ?
C8 C9 C10 114.5(5) . . ?
C10 C9 H9 110.4 . . ?
O2 C1 C2 108.6(5) . . ?
O3 C1 O2 121.0(5) . . ?
O3 C1 C2 130.4(6) . . ?
O1 C11 C12 119.9(5) . . ?
O1 C11 C10 121.6(5) . . ?
C12 C11 C10 118.5(5) . . ?
C17 C12 C11 118.5(5) . . ?
C17 C12 C13 119.3(5) . . ?
C13 C12 C11 122.2(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(6) . . ?
C15 C16 H16 120.0 . . ?
C2 C3 C4 124.0(6) . . ?
C2 C3 C5 114.9(5) . . ?
C5 C3 C4 121.0(6) . . ?
C8 C7 H7 121.4 . . ?
C8 C7 C6 117.3(6) . . ?
C6 C7 H7 121.4 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C5 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.6(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5 119.2 . . ?
C6 C5 C3 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 C9 111.9(5) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9800(18)
2 0.0200(18)

