# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_yy137
_database_code_depnum_ccdc_archive 'CCDC 2204390'
loop_
_audit_author_name
_audit_author_address
'Yahui Chen'
;Ewha Womans University
China
;
_audit_update_record             
;
2022-08-30 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_audit_creation_date             2022-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Chen-20220829
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 O2'
_chemical_formula_sum            'C7 H6 O2'
_chemical_formula_weight         122.12
_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.502(3)
_cell_length_b                   5.137(3)
_cell_length_c                   21.927(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.045(16)
_cell_angle_gamma                90
_cell_volume                     615.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    254
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      19.5694
_cell_measurement_theta_min      3.7340
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.01
_exptl_special_details           
;

;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.1465
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2498
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.040
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_min         1.872
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                400
_reflns_number_total             1074
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.048(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         1074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0929P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4213(6) 0.4725(6) 0.60341(15) 0.0500(15) Uani 1 1 d G . . . .
C2 C 0.6001(5) 0.5096(7) 0.65319(18) 0.0615(17) Uani 1 1 d G . . . .
H2 H 0.740380 0.406911 0.657459 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5693(7) 0.7002(8) 0.69658(15) 0.0732(19) Uani 1 1 d G . . . .
H3 H 0.688953 0.725029 0.729884 0.088 Uiso 1 1 calc R U . . .
C4 C 0.3597(8) 0.8537(7) 0.69020(17) 0.0724(18) Uani 1 1 d G . . . .
H4 H 0.339074 0.981261 0.719232 0.087 Uiso 1 1 calc R U . . .
C5 C 0.1809(6) 0.8167(7) 0.6404(2) 0.075(2) Uani 1 1 d G . . . .
H5 H 0.040620 0.919376 0.636153 0.090 Uiso 1 1 calc R U . . .
C6 C 0.2117(5) 0.6261(7) 0.59703(15) 0.0646(18) Uani 1 1 d G . . . .
H6 H 0.092043 0.601258 0.563727 0.077 Uiso 1 1 calc R U . . .
C7 C 0.4628(10) 0.2692(10) 0.5582(3) 0.0551(16) Uani 1 1 d . . . . .
O1 O 0.6552(6) 0.1379(7) 0.56489(17) 0.0675(13) Uani 1 1 d . . . . .
O2 O 0.2937(7) 0.2377(7) 0.51317(19) 0.0744(14) Uani 1 1 d . . . . .
H2A H 0.315517 0.099737 0.495813 0.112 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.477(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C7 O1 1.248(5) . ?
C7 O2 1.281(5) . ?
O2 H2A 0.8200 . ?

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 C6 120.0 . . ?
C2 C1 C7 118.1(3) . . ?
C6 C1 C7 121.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 120.1(4) . . ?
O1 C7 O2 123.2(5) . . ?
O2 C7 C1 116.7(5) . . ?
C7 O2 H2A 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
C1 C2 C3 C4 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C7 O1 -0.7(6) . . . . ?
C2 C1 C7 O2 179.3(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C7 O1 178.8(4) . . . . ?
C6 C1 C7 O2 -1.2(6) . . . . ?
C7 C1 C2 C3 179.5(4) . . . . ?
C7 C1 C6 C5 -179.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
