# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_zhangchsh_0412_3_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2169290'
loop_
_audit_author_name
_audit_author_address
'Chang-sheng Zhang'
;LanZhou University
China
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-15
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   5.2470(2)
_cell_length_b                   8.2089(2)
_cell_length_c                   28.1307(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1211.65(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1610
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.403
_diffrn_reflns_theta_min         3.142
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     62.00 116.00   1.00    0.12    --   47.45  57.00-150.00   54
  2  ω    126.00 152.00   1.00    0.40    --  107.75  37.00 -60.00   26
  3  ω    146.00 172.00   1.00    0.40    --  107.75  37.00-180.00   26
  4  ω    102.00 128.00   1.00    0.40    --  107.75  37.00-180.00   26
  5  ω    -21.00   5.00   1.00    0.12    --   47.45 -19.00 -60.00   26
  6  ω    -19.00  15.00   1.00    0.12    --   47.45 -19.00-150.00   34
  7  ω     37.00  63.00   1.00    0.40    --  107.75-125.00 -60.00   26
  8  ω     37.00  63.00   1.00    0.40    --  107.75-125.00-180.00   26
  9  ω     76.00 108.00   1.00    0.40    --  107.75-109.00-144.00   32
 10  ω     86.00 112.00   1.00    0.40    --  107.75-125.00 -60.00   26
 11  ω     80.00 106.00   1.00    0.40    --  107.75 -99.00   0.00   26
 12  ω     -9.00  33.00   1.00    0.12    --   47.45 -49.00  98.00   42
 13  ω     30.00 108.00   1.00    0.12    --   47.45-150.00  66.00   78
 14  ω     58.00  99.00   1.00    0.40    --  107.75 -99.00  90.00   41
 15  ω     72.00 100.00   1.00    0.40    --  107.75 -77.00  90.00   28
 16  ω     35.00  62.00   1.00    0.40    --  107.75 -57.00 -60.00   27
 17  ω     51.00 102.00   1.00    0.40    --  107.75 -77.00-150.00   51
 18  ω     37.00  62.00   1.00    0.40    --  107.75 -57.00-180.00   25
 19  ω   -105.00 -71.00   1.00    0.40    -- -100.00 109.00 -48.00   34
 20  ω   -104.00 -40.00   1.00    0.40    -- -100.00 122.00 -49.00   64
 21  ω    -63.00 -37.00   1.00    0.40    -- -100.00 125.00-120.00   26
 22  ω   -112.00 -76.00   1.00    0.40    -- -100.00 125.00-120.00   36
 23  ω    -67.00 -29.00   1.00    0.40    -- -100.00 125.00  90.00   38
 24  ω   -112.00 -86.00   1.00    0.40    -- -100.00 125.00  90.00   26
 25  ω    -83.00 -29.00   1.00    0.40    -- -100.00  72.00  68.00   54
 26  ω    -69.00 -44.00   1.00    0.40    -- -100.00  57.00 -30.00   25
 27  ω    -53.00 -27.00   1.00    0.40    -- -100.00  57.00 -90.00   26
 28  ω    -54.00 -28.00   1.00    0.40    -- -100.00  49.00-114.00   26
 29  ω   -171.00 -97.00   1.00    0.40    -- -100.00 -19.00   0.00   74
 30  ω   -170.00-131.00   1.00    0.40    -- -100.00 -37.00   0.00   39
 31  ω   -161.00 -80.00   1.00    0.40    -- -100.00 -72.00 -61.00   81
 32  ω   -123.00 -97.00   1.00    0.40    -- -100.00 -37.00   0.00   26
 33  ω   -168.00-141.00   1.00    0.40    -- -100.00 -49.00  98.00   27
 34  ω   -173.00-135.00   1.00    0.40    -- -100.00 -37.00 150.00   38
 35  ω   -122.00 -96.00   1.00    0.40    -- -100.00 -37.00 150.00   26
 36  ω   -113.00 -88.00   1.00    0.40    -- -100.00 -49.00  98.00   25
 37  ω   -123.00 -94.00   1.00    0.40    -- -100.00 -99.00  90.00   29
 38  ω   -165.00-132.00   1.00    0.40    -- -100.00 -99.00  90.00   33
 39  ω   -165.00 -77.00   1.00    0.40    -- -100.00-150.00  66.00   88
 40  ω   -117.00 -66.00   1.00    0.12    --  -47.45-150.00  66.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024211000
_diffrn_orient_matrix_UB_12      0.1498838000
_diffrn_orient_matrix_UB_13      0.0329667000
_diffrn_orient_matrix_UB_21      -0.2921600000
_diffrn_orient_matrix_UB_22      0.0099163000
_diffrn_orient_matrix_UB_23      -0.0045271000
_diffrn_orient_matrix_UB_31      -0.0288140000
_diffrn_orient_matrix_UB_32      -0.1126416000
_diffrn_orient_matrix_UB_33      0.0434698000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2623
_reflns_number_total             2834
_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.112
_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)+(0.1504P)²+0.0769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.1994
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.504(7)
 0.496(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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
O1 O 0.2266(5) 0.7101(3) 0.69060(9) 0.0375(6) Uani 1 1 d . . . . .
O2 O -0.0111(6) 0.7152(4) 0.75609(10) 0.0445(7) Uani 1 1 d . . . . .
C1 C 0.6316(10) 0.4917(5) 0.39457(15) 0.0483(10) Uani 1 1 d . . . . .
H1 H 0.760990 0.532609 0.374171 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4468(9) 0.3901(4) 0.37675(13) 0.0412(9) Uani 1 1 d . . . . .
H2 H 0.446788 0.360720 0.344087 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2610(10) 0.3314(6) 0.40697(15) 0.0510(10) Uani 1 1 d . . . . .
H3 H 0.132722 0.260891 0.394967 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2594(9) 0.3741(5) 0.45444(15) 0.0443(9) Uani 1 1 d . . . . .
H4 H 0.129989 0.332270 0.474676 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4449(6) 0.4776(3) 0.47316(12) 0.0283(7) Uani 1 1 d . . . . .
C6 C 0.6300(9) 0.5347(5) 0.44216(14) 0.0443(9) Uani 1 1 d . . . . .
H6 H 0.759166 0.605143 0.453897 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4444(6) 0.5228(3) 0.52453(12) 0.0277(7) Uani 1 1 d . . . . .
C8 C 0.2577(8) 0.4664(5) 0.55560(14) 0.0419(9) Uani 1 1 d . . . . .
H8 H 0.124695 0.399334 0.543656 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2609(8) 0.5054(5) 0.60336(14) 0.0431(9) Uani 1 1 d . . . . .
H9 H 0.130201 0.465362 0.623595 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6325(8) 0.6229(4) 0.54380(13) 0.0376(8) Uani 1 1 d . . . . .
H10 H 0.761842 0.665012 0.523620 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6352(8) 0.6626(4) 0.59168(14) 0.0400(8) Uani 1 1 d . . . . .
H11 H 0.764856 0.732154 0.603650 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4525(7) 0.6024(4) 0.62216(12) 0.0314(7) Uani 1 1 d . . . . .
C13 C 0.4655(7) 0.6378(4) 0.67452(12) 0.0335(7) Uani 1 1 d . . . . .
H13 H 0.607181 0.716628 0.680483 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5007(8) 0.4903(4) 0.70693(13) 0.0383(8) Uani 1 1 d . . . . .
H14A H 0.414545 0.392790 0.693868 0.046 Uiso 1 1 calc R U . . .
H14B H 0.683451 0.465601 0.711912 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3745(8) 0.5473(4) 0.75277(13) 0.0384(8) Uani 1 1 d . . . . .
H15A H 0.297014 0.454798 0.770134 0.046 Uiso 1 1 calc R U . . .
H15B H 0.498652 0.602562 0.773804 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1743(7) 0.6639(4) 0.73553(13) 0.0346(8) Uani 1 1 d . . . . .


_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 C13 1.459(4) . ?
O1 C16 1.348(4) . ?
O2 C16 1.207(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(6) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(5) . ?
C5 C6 1.387(5) . ?
C5 C7 1.492(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(5) . ?
C7 C10 1.394(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(5) . ?
C9 H9 0.9500 . ?
C9 C12 1.387(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(5) . ?
C12 C13 1.503(5) . ?
C13 H13 1.0000 . ?
C13 C14 1.527(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.502(5) . ?

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
C16 O1 C13 110.5(3) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.2(4) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C7 121.0(3) . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 C7 121.7(3) . . ?
C1 C6 C5 121.7(4) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C5 121.8(3) . . ?
C8 C7 C10 116.7(3) . . ?
C10 C7 C5 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C12 120.9(4) . . ?
C12 C9 H9 119.6 . . ?
C7 C10 H10 119.2 . . ?
C11 C10 C7 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C9 C12 C13 121.2(3) . . ?
C11 C12 C9 118.2(3) . . ?
C11 C12 C13 120.6(3) . . ?
O1 C13 C12 110.1(3) . . ?
O1 C13 H13 108.9 . . ?
O1 C13 C14 104.0(3) . . ?
C12 C13 H13 108.9 . . ?
C12 C13 C14 116.0(3) . . ?
C14 C13 H13 108.9 . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C15 C14 C13 102.1(3) . . ?
C15 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C16 C15 C14 103.1(3) . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
O1 C16 C15 109.9(3) . . ?
O2 C16 O1 121.0(3) . . ?
O2 C16 C15 129.1(3) . . ?

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 C13 C14 C15 -31.2(3) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C3 C4 C5 C7 -179.6(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C4 C5 C7 C8 -1.1(5) . . . . ?
C4 C5 C7 C10 178.4(3) . . . . ?
C5 C7 C8 C9 178.5(4) . . . . ?
C5 C7 C10 C11 -178.7(3) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C5 C7 C8 179.6(4) . . . . ?
C6 C5 C7 C10 -0.9(5) . . . . ?
C7 C5 C6 C1 179.5(4) . . . . ?
C7 C8 C9 C12 -0.3(7) . . . . ?
C7 C10 C11 C12 0.7(6) . . . . ?
C8 C7 C10 C11 0.8(5) . . . . ?
C8 C9 C12 C11 1.8(6) . . . . ?
C8 C9 C12 C13 -176.6(4) . . . . ?
C9 C12 C13 O1 -56.1(4) . . . . ?
C9 C12 C13 C14 61.6(5) . . . . ?
C10 C7 C8 C9 -1.1(6) . . . . ?
C10 C11 C12 C9 -2.1(6) . . . . ?
C10 C11 C12 C13 176.3(3) . . . . ?
C11 C12 C13 O1 125.6(3) . . . . ?
C11 C12 C13 C14 -116.8(4) . . . . ?
C12 C13 C14 C15 -152.2(3) . . . . ?
C13 O1 C16 O2 177.4(3) . . . . ?
C13 O1 C16 C15 -2.6(4) . . . . ?
C13 C14 C15 C16 29.3(4) . . . . ?
C14 C15 C16 O1 -17.6(4) . . . . ?
C14 C15 C16 O2 162.3(4) . . . . ?
C16 O1 C13 C12 146.7(3) . . . . ?
C16 O1 C13 C14 21.9(3) . . . . ?

_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 3.656
_oxdiff_exptl_absorpt_empirical_full_min 0.344
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.504(7) 11998 861 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.496(7) 0 861 nmt -0.9875 -0.0093 0.0300 0.0194 -0.9985 -0.0033 0.8668
-0.0383 0.9868

_twin_special_details            
;
Component 2 rotated by 179.2392° 
around [0.02 -0.00 1.00] (reciprocal) or [0.40 -0.02 0.92] (direct)
;
####################################################################### 
# 
# 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_zhangchsh_0412_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2169293'
loop_
_audit_author_name
_audit_author_address
'Chang-sheng Zhang'
;LanZhou University
China
;
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-04-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 O3'
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_chemical_absolute_configuration AD
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.7960(2)
_cell_length_b                   10.4133(2)
_cell_length_c                   10.7857(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     987.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.6670
_cell_measurement_theta_min      4.1060
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3439
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.354
_diffrn_reflns_theta_min         5.907
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  22.00   0.50    0.05    --   47.57 -19.00  60.00   86
  2  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00 120.00   50
  3  ω    127.00 172.00   0.50    0.05    --  107.75  37.00-150.00   90
  4  ω     98.00 124.00   0.50    0.05    --  107.75  37.00-150.00   52
  5  ω    -24.00  10.00   0.50    0.05    --  -47.57  17.00 -69.00   68
  6  ω    -10.00  28.00   0.50    0.05    --  -47.57  19.00  60.00   76
  7  ω    -44.00   8.00   0.50    0.05    --  -47.57  37.00  30.00  104
  8  ω   -112.00 -55.00   0.50    0.05    -- -100.00 133.00 147.00  114
  9  ω   -149.00-109.00   0.50    0.05    -- -100.00 -17.00 121.00   80
 10  ω   -167.00-139.00   0.50    0.05    -- -100.00-109.00 -24.00   56
 11  ω     78.00 106.00   0.50    0.05    --  107.75-125.00  30.00   56
 12  ω     35.00  61.00   0.50    0.05    --  107.75-125.00   0.00   52
 13  ω     35.00  71.00   0.50    0.05    --  107.75-125.00  30.00   72
 14  ω     71.00 102.00   0.50    0.05    --  107.75-125.00   0.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344154000
_diffrn_orient_matrix_UB_12      -0.1321906000
_diffrn_orient_matrix_UB_13      0.0574493000
_diffrn_orient_matrix_UB_21      0.0159795000
_diffrn_orient_matrix_UB_22      -0.0579983000
_diffrn_orient_matrix_UB_23      -0.1309105000
_diffrn_orient_matrix_UB_31      0.1708422000
_diffrn_orient_matrix_UB_32      0.0322976000
_diffrn_orient_matrix_UB_33      0.0007956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.548
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                1732
_reflns_number_total             1765
_reflns_odcompleteness_completeness 98.77
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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         0.177
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      0.877
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
;
_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
O1 O 0.48782(15) 0.42239(12) 1.00560(10) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.30401(11) 0.24364(10) 0.46822(10) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.33331(16) 0.13272(15) 0.29346(12) 0.0496(4) Uani 1 1 d . . . . .
C1 C 0.41456(18) 0.38987(15) 0.89799(14) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.30040(18) 0.46171(15) 0.84432(14) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.268660 0.541235 0.878850 0.039 Uiso 1 1 calc R . . . .
C3 C 0.23361(17) 0.41240(14) 0.73709(14) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.154607 0.459489 0.697843 0.035 Uiso 1 1 calc R . . . .
C4 C 0.27985(17) 0.29587(14) 0.68612(12) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.39945(16) 0.22705(14) 0.74126(13) 0.0267(3) Uani 1 1 d . . . . .
H5 H 0.434029 0.148774 0.705881 0.032 Uiso 1 1 calc R . . . .
C6 C 0.46616(16) 0.27496(14) 0.84788(13) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.59447(18) 0.22771(16) 0.92871(15) 0.0355(4) Uani 1 1 d . . . . .
H7A H 0.694999 0.248297 0.892547 0.043 Uiso 1 1 calc R . . . .
H7B H 0.587502 0.134117 0.943809 0.043 Uiso 1 1 calc R . . . .
C8 C 0.56420(19) 0.30484(19) 1.04666(16) 0.0394(4) Uani 1 1 d . . . . .
H8A H 0.498452 0.255812 1.104180 0.047 Uiso 1 1 calc R . . . .
H8B H 0.660761 0.325522 1.089382 0.047 Uiso 1 1 calc R . . . .
C9 C 0.19876(15) 0.24467(13) 0.57463(13) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.111616 0.302867 0.554924 0.032 Uiso 1 1 calc R . . . .
C10 C 0.26882(18) 0.14566(15) 0.39069(15) 0.0333(4) Uani 1 1 d . . . . .
C11 C 0.14226(19) 0.06682(15) 0.44572(16) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.163449 -0.026148 0.437360 0.045 Uiso 1 1 calc R . . . .
H11B H 0.044058 0.086413 0.405065 0.045 Uiso 1 1 calc R . . . .
C12 C 0.14005(18) 0.10687(15) 0.58128(15) 0.0350(4) Uani 1 1 d . . . . .
H12A H 0.207875 0.052027 0.631894 0.042 Uiso 1 1 calc R . . . .
H12B H 0.035872 0.103483 0.615858 0.042 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
O1 C1 1.3700(18) . ?
O1 C8 1.465(2) . ?
O2 C9 1.4745(16) . ?
O2 C10 1.3550(18) . ?
O3 C10 1.200(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.4963(18) . ?
C5 C6 1.3841(19) . ?
C6 C7 1.509(2) . ?
C7 C8 1.528(2) . ?
C9 C12 1.527(2) . ?
C10 C11 1.505(2) . ?
C11 C12 1.521(2) . ?

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 C8 105.39(12) . . ?
C10 O2 C9 110.03(11) . . ?
O1 C1 C2 124.32(14) . . ?
O1 C1 C6 112.88(13) . . ?
C2 C1 C6 122.79(14) . . ?
C1 C2 C3 117.06(14) . . ?
C4 C3 C2 121.66(14) . . ?
C3 C4 C5 119.73(13) . . ?
C3 C4 C9 119.23(13) . . ?
C5 C4 C9 121.02(12) . . ?
C6 C5 C4 119.03(13) . . ?
C1 C6 C7 107.49(13) . . ?
C5 C6 C1 119.69(14) . . ?
C5 C6 C7 132.82(15) . . ?
C6 C7 C8 100.33(13) . . ?
O1 C8 C7 105.52(13) . . ?
O2 C9 C4 109.20(10) . . ?
O2 C9 C12 104.01(11) . . ?
C4 C9 C12 117.28(12) . . ?
O2 C10 C11 109.65(13) . . ?
O3 C10 O2 121.06(16) . . ?
O3 C10 C11 129.27(15) . . ?
C10 C11 C12 103.83(12) . . ?
C11 C12 C9 102.02(12) . . ?

_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 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.529
