# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20220623-1
_database_code_depnum_ccdc_archive 'CCDC 2225401'
loop_
_audit_author_name
_audit_author_address
R.Qi
;jiaxing university
China
;
_audit_update_record             
;
2022-12-09 deposited with the CCDC.	2023-06-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 O'
_chemical_formula_sum            'C14 H9 O'
_chemical_formula_weight         193.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'

_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.8930(10)
_cell_length_b                   7.7491(4)
_cell_length_c                   13.6613(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.970(5)
_cell_angle_gamma                90
_cell_volume                     1893.93(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2400
_cell_measurement_theta_min      4.0480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.830
_diffrn_reflns_theta_min         4.944
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     79.00 109.00   1.00    1.00    --   36.33 178.00  30.00   30
  2  ω     43.00  69.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  3  ω     12.00  41.00   1.00    1.00    --   36.33  77.00 150.00   29
  4  ω     -1.00  25.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  5  ω     54.00 103.00   1.00    1.00    --   36.33  77.00-150.00   49
  6  ω     12.00  49.00   1.00    1.00    --   36.33  77.00-150.00   37
  7  ω     58.00 109.00   1.00    1.00    --   36.33 178.00  90.00   51
  8  ω     63.00  89.00   1.00    1.00    --   36.33-178.00-150.00   26
  9  ω     65.00 100.00   1.00    1.00    --   36.33  77.00 150.00   35
 10  ω     62.00 113.00   1.00    2.38    --  108.00-111.00 -30.00   51
 11  ω     49.00 124.00   1.00    2.38    --  108.00 -61.00-180.00   75
 12  ω     45.00  88.00   1.00    2.38    --  108.00 -77.00  90.00   43
 13  ω     83.00 123.00   1.00    2.38    --  108.00 -45.00  30.00   40
 14  ω     43.00  68.00   1.00    2.38    --  108.00 -45.00  30.00   25
 15  ω     44.00 107.00   1.00    2.38    --  108.00 -95.00-180.00   63
 16  ω     94.00 165.00   1.00    2.38    --  108.00  45.00   0.00   71
 17  ω     94.00 136.00   1.00    2.38    --  108.00  61.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0840837000
_diffrn_orient_matrix_UB_12      -0.0059262000
_diffrn_orient_matrix_UB_13      0.0262532000
_diffrn_orient_matrix_UB_21      -0.0168607000
_diffrn_orient_matrix_UB_22      -0.1122538000
_diffrn_orient_matrix_UB_23      0.0900515000
_diffrn_orient_matrix_UB_31      0.0085461000
_diffrn_orient_matrix_UB_32      -0.1637907000
_diffrn_orient_matrix_UB_33      -0.0626065000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1511
_reflns_number_total             1819
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.387
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.085
_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)+(0.1063P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
;
_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
O001 O 0.61696(10) -0.00674(19) 0.31860(15) 0.0821(6) Uani 1 1 d . . . . .
C002 C 0.74856(8) 0.38370(18) 0.44117(9) 0.0351(4) Uani 1 1 d . . . . .
H002 H 0.779138 0.480546 0.418921 0.042 Uiso 1 1 calc R . . . .
C003 C 0.78278(9) 0.22046(19) 0.40233(10) 0.0363(4) Uani 1 1 d . . . . .
C004 C 0.66947(9) 0.41589(19) 0.40633(10) 0.0384(4) Uani 1 1 d . . . . .
C005 C 0.62528(9) 0.2851(2) 0.36548(11) 0.0419(4) Uani 1 1 d . . . . .
C006 C 0.73784(10) 0.0872(2) 0.36498(11) 0.0415(4) Uani 1 1 d . . . . .
C007 C 0.85987(9) 0.1940(2) 0.40781(11) 0.0451(4) Uani 1 1 d . . . . .
H007 H 0.890866 0.282927 0.429561 0.054 Uiso 1 1 calc R . . . .
C008 C 0.63722(10) 0.5778(2) 0.42028(13) 0.0476(4) Uani 1 1 d . . . . .
H008 H 0.665870 0.666698 0.447025 0.057 Uiso 1 1 calc R . . . .
C009 C 0.65667(10) 0.1114(2) 0.34828(12) 0.0489(5) Uani 1 1 d . . . . .
C00A C 0.55043(10) 0.3174(3) 0.34015(13) 0.0525(5) Uani 1 1 d . . . . .
H00A H 0.521298 0.229718 0.312969 0.063 Uiso 1 1 calc R . . . .
C00B C 0.56322(11) 0.6077(3) 0.39488(14) 0.0570(5) Uani 1 1 d . . . . .
H00B H 0.542589 0.716416 0.404659 0.068 Uiso 1 1 calc R . . . .
C00C C 0.89087(11) 0.0380(3) 0.38147(13) 0.0561(5) Uani 1 1 d . . . . .
H00C H 0.942353 0.022599 0.386272 0.067 Uiso 1 1 calc R . . . .
C00D C 0.77000(12) -0.0698(2) 0.33859(13) 0.0537(5) Uani 1 1 d . . . . .
H00D H 0.739740 -0.158046 0.314340 0.064 Uiso 1 1 calc R . . . .
C00E C 0.51966(11) 0.4771(3) 0.35502(14) 0.0583(5) Uani 1 1 d . . . . .
H00E H 0.469820 0.497483 0.338409 0.070 Uiso 1 1 calc R . . . .
C00F C 0.84602(12) -0.0957(3) 0.34800(14) 0.0596(5) Uani 1 1 d . . . . .
H00F H 0.866874 -0.201769 0.332036 0.071 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
O001 C009 1.224(2) . ?
C002 C002 1.607(3) 2_656 ?
C002 H002 0.9800 . ?
C002 C003 1.506(2) . ?
C002 C004 1.506(2) . ?
C003 C006 1.400(2) . ?
C003 C007 1.395(2) . ?
C004 C005 1.396(2) . ?
C004 C008 1.395(2) . ?
C005 C009 1.478(2) . ?
C005 C00A 1.400(2) . ?
C006 C009 1.478(2) . ?
C006 C00D 1.396(2) . ?
C007 H007 0.9300 . ?
C007 C00C 1.381(2) . ?
C008 H008 0.9300 . ?
C008 C00B 1.383(3) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.371(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.384(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.384(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.379(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?

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
C002 C002 H002 107.6 2_656 . ?
C003 C002 C002 110.25(9) . 2_656 ?
C003 C002 H002 107.6 . . ?
C003 C002 C004 114.41(12) . . ?
C004 C002 C002 109.26(14) . 2_656 ?
C004 C002 H002 107.6 . . ?
C006 C003 C002 120.91(14) . . ?
C007 C003 C002 120.79(14) . . ?
C007 C003 C006 118.20(15) . . ?
C005 C004 C002 121.92(14) . . ?
C008 C004 C002 119.63(14) . . ?
C008 C004 C005 118.33(15) . . ?
C004 C005 C009 120.68(15) . . ?
C004 C005 C00A 120.10(16) . . ?
C00A C005 C009 119.22(15) . . ?
C003 C006 C009 121.30(15) . . ?
C00D C006 C003 120.02(16) . . ?
C00D C006 C009 118.61(16) . . ?
C003 C007 H007 119.5 . . ?
C00C C007 C003 121.05(16) . . ?
C00C C007 H007 119.5 . . ?
C004 C008 H008 119.6 . . ?
C00B C008 C004 120.88(17) . . ?
C00B C008 H008 119.6 . . ?
O001 C009 C005 120.91(18) . . ?
O001 C009 C006 121.30(17) . . ?
C005 C009 C006 117.76(14) . . ?
C005 C00A H00A 119.7 . . ?
C00E C00A C005 120.66(17) . . ?
C00E C00A H00A 119.7 . . ?
C008 C00B H00B 119.8 . . ?
C008 C00B C00E 120.43(17) . . ?
C00E C00B H00B 119.8 . . ?
C007 C00C H00C 119.7 . . ?
C007 C00C C00F 120.57(18) . . ?
C00F C00C H00C 119.7 . . ?
C006 C00D H00D 119.6 . . ?
C00F C00D C006 120.89(18) . . ?
C00F C00D H00D 119.6 . . ?
C00A C00E C00B 119.59(17) . . ?
C00A C00E H00E 120.2 . . ?
C00B C00E H00E 120.2 . . ?
C00C C00F H00F 120.4 . . ?
C00D C00F C00C 119.17(17) . . ?
C00D C00F H00F 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.975
_oxdiff_exptl_absorpt_empirical_full_min 0.643
