# 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_220330a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2295482'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O4'
_chemical_formula_sum            'C21 H16 O4'
_chemical_formula_weight         332.34
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.460(7)
_cell_length_b                   11.802(9)
_cell_length_c                   17.491(14)
_cell_angle_alpha                79.660(10)
_cell_angle_beta                 83.815(11)
_cell_angle_gamma                89.445(11)
_cell_volume                     1708(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3933
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      23.087
_cell_measurement_theta_min      2.290
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1284 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8207.
The λ/2 correction factor is Not present.
;
_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    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19706
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         1.190
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3872
_reflns_number_total             7626
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      0.995
_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)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
  C38(H38), C39(H39), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_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 0.53306(15) 0.33729(11) 0.35690(8) 0.0598(4) Uani 1 1 d . . . . .
O2 O 0.7816(2) 0.68727(14) 0.34242(10) 0.1006(6) Uani 1 1 d . . . . .
O3 O 0.77419(18) 0.55841(15) 0.45248(10) 0.0831(5) Uani 1 1 d . . . . .
O4 O 0.4303(2) 0.70985(12) 0.29347(10) 0.0945(6) Uani 1 1 d . . . . .
H4 H 0.389509 0.772896 0.294765 0.142 Uiso 1 1 calc R U . . .
C1 C 0.5125(2) 0.40383(16) 0.28348(11) 0.0508(5) Uani 1 1 d . . . . .
C2 C 0.5798(2) 0.50969(15) 0.27619(11) 0.0503(5) Uani 1 1 d . . . . .
C3 C 0.6453(2) 0.50986(16) 0.34854(11) 0.0532(5) Uani 1 1 d . . . . .
C4 C 0.7351(3) 0.5930(2) 0.37638(14) 0.0697(6) Uani 1 1 d . . . . .
C5 C 0.7398(3) 0.4510(3) 0.49757(13) 0.0831(8) Uani 1 1 d . . . . .
C6 C 0.6602(3) 0.3718(2) 0.47080(13) 0.0748(7) Uani 1 1 d . . . . .
H6 H 0.636668 0.299218 0.500465 0.090 Uiso 1 1 calc R U . . .
C7 C 0.6140(2) 0.40466(18) 0.39510(12) 0.0572(5) Uani 1 1 d . . . . .
C8 C 0.4207(2) 0.34753(16) 0.23276(12) 0.0595(5) Uani 1 1 d . . . . .
H8A H 0.386805 0.406211 0.191626 0.071 Uiso 1 1 calc R U . . .
H8B H 0.325797 0.312404 0.263683 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5113(2) 0.25621(15) 0.19554(12) 0.0482(5) Uani 1 1 d . . . . .
C10 C 0.5719(3) 0.27843(19) 0.11818(13) 0.0687(6) Uani 1 1 d . . . . .
H10 H 0.555055 0.349826 0.087857 0.082 Uiso 1 1 calc R U . . .
C11 C 0.6576(3) 0.1958(2) 0.08484(13) 0.0791(7) Uani 1 1 d . . . . .
H11 H 0.697940 0.212040 0.032417 0.095 Uiso 1 1 calc R U . . .
C12 C 0.6832(3) 0.0902(2) 0.12877(14) 0.0732(7) Uani 1 1 d . . . . .
H12 H 0.742050 0.035207 0.106440 0.088 Uiso 1 1 calc R U . . .
C13 C 0.6221(3) 0.06613(17) 0.20521(14) 0.0633(6) Uani 1 1 d . . . . .
H13 H 0.638144 -0.005794 0.235026 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5363(2) 0.14854(16) 0.23856(12) 0.0536(5) Uani 1 1 d . . . . .
H14 H 0.494700 0.131259 0.290778 0.064 Uiso 1 1 calc R U . . .
C15 C 0.5777(2) 0.60625(16) 0.20899(11) 0.0528(5) Uani 1 1 d . . . . .
C16 C 0.4997(3) 0.70749(17) 0.22034(14) 0.0628(6) Uani 1 1 d . . . . .
C17 C 0.4908(3) 0.79794(19) 0.15886(16) 0.0763(7) Uani 1 1 d . . . . .
H17 H 0.436349 0.864418 0.166753 0.092 Uiso 1 1 calc R U . . .
C18 C 0.5628(3) 0.7891(2) 0.08588(16) 0.0844(7) Uani 1 1 d . . . . .
H18 H 0.557645 0.850121 0.044418 0.101 Uiso 1 1 calc R U . . .
C19 C 0.6424(3) 0.6908(2) 0.07383(14) 0.0853(7) Uani 1 1 d . . . . .
H19 H 0.691029 0.685069 0.024404 0.102 Uiso 1 1 calc R U . . .
C20 C 0.6497(3) 0.60042(19) 0.13560(12) 0.0681(6) Uani 1 1 d . . . . .
H20 H 0.704570 0.534271 0.127316 0.082 Uiso 1 1 calc R U . . .
C21 C 0.8040(3) 0.4417(3) 0.57453(14) 0.1218(11) Uani 1 1 d . . . . .
H21A H 0.916617 0.455949 0.566239 0.183 Uiso 1 1 calc R U . . .
H21B H 0.783201 0.365750 0.604310 0.183 Uiso 1 1 calc R U . . .
H21C H 0.753539 0.497462 0.602591 0.183 Uiso 1 1 calc R U . . .
O5 O 0.03389(15) 1.22698(11) 0.36205(8) 0.0577(4) Uani 1 1 d . . . . .
O6 O 0.28123(17) 0.95793(13) 0.46131(9) 0.0734(4) Uani 1 1 d . . . . .
O7 O 0.2959(2) 0.88453(13) 0.35309(9) 0.0904(5) Uani 1 1 d . . . . .
O8 O -0.0511(2) 0.88176(12) 0.30432(9) 0.0848(5) Uani 1 1 d . . . . .
H8 H -0.088676 0.817339 0.306451 0.127 Uiso 1 1 calc R U . . .
C22 C 0.0157(2) 1.19684(16) 0.28971(11) 0.0486(5) Uani 1 1 d . . . . .
C23 C 0.0861(2) 1.09484(15) 0.28337(11) 0.0473(5) Uani 1 1 d . . . . .
C24 C 0.1521(2) 1.05819(15) 0.35633(11) 0.0485(5) Uani 1 1 d . . . . .
C25 C 0.2443(3) 0.96156(19) 0.38523(12) 0.0613(6) Uani 1 1 d . . . . .
C26 C 0.2437(3) 1.0423(2) 0.50510(12) 0.0728(7) Uani 1 1 d . . . . .
C27 C 0.1629(3) 1.1356(2) 0.47686(12) 0.0697(6) Uani 1 1 d . . . . .
H27 H 0.137949 1.193807 0.505504 0.084 Uiso 1 1 calc R U . . .
C28 C 0.1177(2) 1.14056(17) 0.40115(12) 0.0534(5) Uani 1 1 d . . . . .
C29 C -0.0802(2) 1.27736(16) 0.23806(12) 0.0584(5) Uani 1 1 d . . . . .
H29A H -0.175323 1.296927 0.268942 0.070 Uiso 1 1 calc R U . . .
H29B H -0.113359 1.237957 0.198250 0.070 Uiso 1 1 calc R U . . .
C30 C 0.0059(2) 1.38798(15) 0.19811(12) 0.0490(5) Uani 1 1 d . . . . .
C31 C 0.0387(2) 1.47213(16) 0.24036(12) 0.0571(5) Uani 1 1 d . . . . .
H31 H 0.003703 1.461733 0.293430 0.069 Uiso 1 1 calc R U . . .
C32 C 0.1222(3) 1.57109(17) 0.20515(15) 0.0700(6) Uani 1 1 d . . . . .
H32 H 0.144464 1.625990 0.234649 0.084 Uiso 1 1 calc R U . . .
C33 C 0.1721(3) 1.58835(19) 0.12700(16) 0.0790(7) Uani 1 1 d . . . . .
H33 H 0.228760 1.654821 0.103248 0.095 Uiso 1 1 calc R U . . .
C34 C 0.1385(3) 1.5072(2) 0.08356(14) 0.0819(7) Uani 1 1 d . . . . .
H34 H 0.170851 1.519170 0.030185 0.098 Uiso 1 1 calc R U . . .
C35 C 0.0556(3) 1.40673(19) 0.11965(13) 0.0685(6) Uani 1 1 d . . . . .
H35 H 0.033885 1.351804 0.090077 0.082 Uiso 1 1 calc R U . . .
C36 C 0.0861(2) 1.03243(15) 0.21755(11) 0.0481(5) Uani 1 1 d . . . . .
C37 C 0.0121(2) 0.92382(17) 0.22961(12) 0.0564(5) Uani 1 1 d . . . . .
C38 C 0.0030(3) 0.86604(18) 0.16845(14) 0.0667(6) Uani 1 1 d . . . . .
H38 H -0.048455 0.794909 0.176905 0.080 Uiso 1 1 calc R U . . .
C39 C 0.0704(3) 0.9139(2) 0.09488(14) 0.0746(7) Uani 1 1 d . . . . .
H39 H 0.064771 0.874625 0.053661 0.090 Uiso 1 1 calc R U . . .
C40 C 0.1459(3) 1.0192(2) 0.08154(13) 0.0761(7) Uani 1 1 d . . . . .
H40 H 0.191159 1.051184 0.031583 0.091 Uiso 1 1 calc R U . . .
C41 C 0.1540(2) 1.07729(18) 0.14289(12) 0.0615(6) Uani 1 1 d . . . . .
H41 H 0.206424 1.148129 0.133797 0.074 Uiso 1 1 calc R U . . .
C42 C 0.3070(3) 1.0130(3) 0.58223(13) 0.1063(10) Uani 1 1 d . . . . .
H42A H 0.253737 0.945263 0.612080 0.159 Uiso 1 1 calc R U . . .
H42B H 0.289057 1.076011 0.609933 0.159 Uiso 1 1 calc R U . . .
H42C H 0.418989 0.998902 0.574472 0.159 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 1.407(2) . ?
O1 C7 1.359(2) . ?
O2 C4 1.211(3) . ?
O3 C4 1.395(3) . ?
O3 C5 1.383(3) . ?
O4 H4 0.8200 . ?
O4 C16 1.354(3) . ?
C1 C2 1.357(3) . ?
C1 C8 1.484(3) . ?
C2 C3 1.435(3) . ?
C2 C15 1.485(3) . ?
C3 C4 1.430(3) . ?
C3 C7 1.368(3) . ?
C5 C6 1.335(3) . ?
C5 C21 1.491(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.407(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.517(3) . ?
C9 C10 1.374(3) . ?
C9 C14 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(3) . ?
C15 C20 1.373(3) . ?
C16 C17 1.380(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O5 C22 1.398(2) . ?
O5 C28 1.361(2) . ?
O6 C25 1.392(3) . ?
O6 C26 1.377(3) . ?
O7 C25 1.207(2) . ?
O8 H8 0.8200 . ?
O8 C37 1.364(2) . ?
C22 C23 1.355(3) . ?
C22 C29 1.487(3) . ?
C23 C24 1.442(3) . ?
C23 C36 1.474(3) . ?
C24 C25 1.423(3) . ?
C24 C28 1.365(3) . ?
C26 C27 1.337(3) . ?
C26 C42 1.487(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.409(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.518(3) . ?
C30 C31 1.386(3) . ?
C30 C35 1.370(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.381(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.366(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.375(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.395(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.403(3) . ?
C36 C41 1.383(3) . ?
C37 C38 1.377(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.374(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.373(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.381(3) . ?
C41 H41 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 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
C7 O1 C1 106.57(15) . . ?
C5 O3 C4 124.54(18) . . ?
C16 O4 H4 109.5 . . ?
O1 C1 C8 115.54(16) . . ?
C2 C1 O1 110.39(17) . . ?
C2 C1 C8 134.04(19) . . ?
C1 C2 C3 105.40(17) . . ?
C1 C2 C15 126.83(19) . . ?
C3 C2 C15 127.69(17) . . ?
C4 C3 C2 133.03(19) . . ?
C7 C3 C2 107.96(17) . . ?
C7 C3 C4 119.0(2) . . ?
O2 C4 O3 117.1(2) . . ?
O2 C4 C3 128.5(2) . . ?
O3 C4 C3 114.4(2) . . ?
O3 C5 C21 110.4(2) . . ?
C6 C5 O3 121.1(2) . . ?
C6 C5 C21 128.5(3) . . ?
C5 C6 H6 121.9 . . ?
C5 C6 C7 116.1(2) . . ?
C7 C6 H6 121.9 . . ?
O1 C7 C3 109.68(19) . . ?
O1 C7 C6 125.6(2) . . ?
C3 C7 C6 124.7(2) . . ?
C1 C8 H8A 108.6 . . ?
C1 C8 H8B 108.6 . . ?
C1 C8 C9 114.44(16) . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C10 C9 C8 120.91(18) . . ?
C10 C9 C14 118.08(19) . . ?
C14 C9 C8 121.00(19) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 121.1(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C2 119.03(18) . . ?
C20 C15 C2 122.77(18) . . ?
C20 C15 C16 118.21(19) . . ?
O4 C16 C15 116.42(19) . . ?
O4 C16 C17 122.7(2) . . ?
C17 C16 C15 120.8(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 121.4(2) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C28 O5 C22 106.26(15) . . ?
C26 O6 C25 124.75(18) . . ?
C37 O8 H8 109.5 . . ?
O5 C22 C29 115.61(17) . . ?
C23 C22 O5 110.94(16) . . ?
C23 C22 C29 133.38(19) . . ?
C22 C23 C24 105.17(17) . . ?
C22 C23 C36 126.90(18) . . ?
C24 C23 C36 127.83(17) . . ?
C25 C24 C23 133.10(19) . . ?
C28 C24 C23 107.53(18) . . ?
C28 C24 C25 119.3(2) . . ?
O6 C25 C24 114.26(19) . . ?
O7 C25 O6 116.3(2) . . ?
O7 C25 C24 129.4(2) . . ?
O6 C26 C42 110.5(2) . . ?
C27 C26 O6 121.1(2) . . ?
C27 C26 C42 128.4(2) . . ?
C26 C27 H27 122.0 . . ?
C26 C27 C28 116.0(2) . . ?
C28 C27 H27 122.0 . . ?
O5 C28 C24 110.10(18) . . ?
O5 C28 C27 125.45(19) . . ?
C24 C28 C27 124.5(2) . . ?
C22 C29 H29A 108.6 . . ?
C22 C29 H29B 108.6 . . ?
C22 C29 C30 114.53(16) . . ?
H29A C29 H29B 107.6 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C31 C30 C29 120.82(19) . . ?
C35 C30 C29 121.03(18) . . ?
C35 C30 C31 118.14(19) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.3(2) . . ?
C32 C31 H31 119.4 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.1 . . ?
C32 C33 C34 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 119.9(2) . . ?
C35 C34 H34 120.0 . . ?
C30 C35 C34 120.9(2) . . ?
C30 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C37 C36 C23 119.57(17) . . ?
C41 C36 C23 122.70(17) . . ?
C41 C36 C37 117.73(18) . . ?
O8 C37 C36 115.91(17) . . ?
O8 C37 C38 123.19(19) . . ?
C38 C37 C36 120.89(19) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 C37 119.7(2) . . ?
C39 C38 H38 120.1 . . ?
C38 C39 H39 119.6 . . ?
C40 C39 C38 120.7(2) . . ?
C40 C39 H39 119.6 . . ?
C39 C40 H40 120.3 . . ?
C39 C40 C41 119.5(2) . . ?
C41 C40 H40 120.3 . . ?
C36 C41 H41 119.3 . . ?
C40 C41 C36 121.5(2) . . ?
C40 C41 H41 119.3 . . ?
C26 C42 H42A 109.5 . . ?
C26 C42 H42B 109.5 . . ?
C26 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

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
_geom_hbond_publ_flag
O4 H4 O7 0.82 1.92 2.665(3) 150.3 . yes
O8 H8 O2 0.82 1.87 2.651(3) 158.9 1_455 yes

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 -0.2(2) . . . . ?
O1 C1 C2 C15 -177.26(16) . . . . ?
O1 C1 C8 C9 -75.0(2) . . . . ?
O3 C5 C6 C7 -0.2(3) . . . . ?
O4 C16 C17 C18 -179.3(2) . . . . ?
C1 O1 C7 C3 -0.3(2) . . . . ?
C1 O1 C7 C6 -179.87(19) . . . . ?
C1 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C7 0.0(2) . . . . ?
C1 C2 C15 C16 115.9(2) . . . . ?
C1 C2 C15 C20 -64.2(3) . . . . ?
C1 C8 C9 C10 -103.6(2) . . . . ?
C1 C8 C9 C14 76.0(2) . . . . ?
C2 C1 C8 C9 107.4(2) . . . . ?
C2 C3 C4 O2 -1.6(4) . . . . ?
C2 C3 C4 O3 179.17(19) . . . . ?
C2 C3 C7 O1 0.2(2) . . . . ?
C2 C3 C7 C6 179.74(19) . . . . ?
C2 C15 C16 O4 -0.1(3) . . . . ?
C2 C15 C16 C17 -177.97(18) . . . . ?
C2 C15 C20 C19 178.4(2) . . . . ?
C3 C2 C15 C16 -60.5(3) . . . . ?
C3 C2 C15 C20 119.4(2) . . . . ?
C4 O3 C5 C6 -1.9(4) . . . . ?
C4 O3 C5 C21 177.77(19) . . . . ?
C4 C3 C7 O1 -177.67(17) . . . . ?
C4 C3 C7 C6 1.9(3) . . . . ?
C5 O3 C4 O2 -175.5(2) . . . . ?
C5 O3 C4 C3 3.8(3) . . . . ?
C5 C6 C7 O1 179.7(2) . . . . ?
C5 C6 C7 C3 0.2(3) . . . . ?
C7 O1 C1 C2 0.3(2) . . . . ?
C7 O1 C1 C8 -177.85(16) . . . . ?
C7 C3 C4 O2 175.6(2) . . . . ?
C7 C3 C4 O3 -3.6(3) . . . . ?
C8 C1 C2 C3 177.5(2) . . . . ?
C8 C1 C2 C15 0.5(3) . . . . ?
C8 C9 C10 C11 178.54(19) . . . . ?
C8 C9 C14 C13 -178.45(17) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C9 C14 C13 1.1(3) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C14 C9 C10 C11 -1.0(3) . . . . ?
C15 C2 C3 C4 -5.5(3) . . . . ?
C15 C2 C3 C7 177.03(18) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C15 0.6(4) . . . . ?
C20 C15 C16 O4 180.0(2) . . . . ?
C20 C15 C16 C17 2.1(3) . . . . ?
C21 C5 C6 C7 -179.9(2) . . . . ?
O5 C22 C23 C24 0.28(19) . . . . ?
O5 C22 C23 C36 177.02(16) . . . . ?
O5 C22 C29 C30 76.1(2) . . . . ?
O6 C26 C27 C28 0.9(3) . . . . ?
O8 C37 C38 C39 -179.7(2) . . . . ?
C22 O5 C28 C24 -0.1(2) . . . . ?
C22 O5 C28 C27 -179.92(18) . . . . ?
C22 C23 C24 C25 -177.5(2) . . . . ?
C22 C23 C24 C28 -0.3(2) . . . . ?
C22 C23 C36 C37 -116.2(2) . . . . ?
C22 C23 C36 C41 62.6(3) . . . . ?
C22 C29 C30 C31 -71.2(2) . . . . ?
C22 C29 C30 C35 107.8(2) . . . . ?
C23 C22 C29 C30 -107.2(2) . . . . ?
C23 C24 C25 O6 -178.74(18) . . . . ?
C23 C24 C25 O7 2.4(4) . . . . ?
C23 C24 C28 O5 0.2(2) . . . . ?
C23 C24 C28 C27 -179.90(18) . . . . ?
C23 C36 C37 O8 -2.2(3) . . . . ?
C23 C36 C37 C38 176.68(18) . . . . ?
C23 C36 C41 C40 -176.98(19) . . . . ?
C24 C23 C36 C37 59.8(3) . . . . ?
C24 C23 C36 C41 -121.4(2) . . . . ?
C25 O6 C26 C27 1.6(3) . . . . ?
C25 O6 C26 C42 -177.54(18) . . . . ?
C25 C24 C28 O5 177.89(15) . . . . ?
C25 C24 C28 C27 -2.2(3) . . . . ?
C26 O6 C25 O7 174.8(2) . . . . ?
C26 O6 C25 C24 -4.2(3) . . . . ?
C26 C27 C28 O5 179.33(19) . . . . ?
C26 C27 C28 C24 -0.5(3) . . . . ?
C28 O5 C22 C23 -0.15(19) . . . . ?
C28 O5 C22 C29 177.25(15) . . . . ?
C28 C24 C25 O6 4.3(3) . . . . ?
C28 C24 C25 O7 -174.5(2) . . . . ?
C29 C22 C23 C24 -176.49(19) . . . . ?
C29 C22 C23 C36 0.3(3) . . . . ?
C29 C30 C31 C32 177.51(18) . . . . ?
C29 C30 C35 C34 -178.3(2) . . . . ?
C30 C31 C32 C33 1.0(3) . . . . ?
C31 C30 C35 C34 0.7(3) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C33 C34 C35 -1.0(4) . . . . ?
C33 C34 C35 C30 0.5(4) . . . . ?
C35 C30 C31 C32 -1.5(3) . . . . ?
C36 C23 C24 C25 5.8(3) . . . . ?
C36 C23 C24 C28 -177.01(17) . . . . ?
C36 C37 C38 C39 1.5(3) . . . . ?
C37 C36 C41 C40 1.8(3) . . . . ?
C37 C38 C39 C40 -0.4(3) . . . . ?
C38 C39 C40 C41 0.0(4) . . . . ?
C39 C40 C41 C36 -0.8(3) . . . . ?
C41 C36 C37 O8 178.92(19) . . . . ?
C41 C36 C37 C38 -2.2(3) . . . . ?
C42 C26 C27 C28 179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20221017i
_database_code_depnum_ccdc_archive 'CCDC 2295483'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_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'
N N 0.0061 0.0033 '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                   6.9547(6)
_cell_length_b                   19.975(2)
_cell_length_c                   12.2707(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.477(4)
_cell_angle_gamma                90
_cell_volume                     1704.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3182
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      25.029
_cell_measurement_theta_min      2.630
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.8421.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.630
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1989
_reflns_number_total             3885
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0143(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.022
_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)+(0.0549P)²+0.1803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1430
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.3501(2) 0.33961(8) 0.47898(13) 0.0498(5) Uani 1 1 d . . . . .
O2 O 0.9328(2) 0.44070(9) 0.40226(13) 0.0557(5) Uani 1 1 d . . . . .
O4 O 0.8064(3) 0.42038(8) 0.20295(14) 0.0576(5) Uani 1 1 d . . . . .
H4 H 0.851330 0.430737 0.262610 0.086 Uiso 1 1 calc R U . . .
N3 N 0.7757(3) 0.46507(9) 0.55891(15) 0.0446(5) Uani 1 1 d . . . . .
H3 H 0.869278 0.491444 0.575329 0.054 Uiso 1 1 calc R U . . .
C1 C 0.4201(3) 0.31021(12) 0.38362(18) 0.0424(6) Uani 1 1 d . . . . .
C2 C 0.5951(3) 0.33540(11) 0.35759(18) 0.0376(5) Uani 1 1 d . . . . .
C3 C 0.6373(3) 0.38511(11) 0.44110(18) 0.0381(5) Uani 1 1 d . . . . .
C4 C 0.7905(3) 0.43002(11) 0.46320(19) 0.0422(6) Uani 1 1 d . . . . .
C5 C 0.6252(4) 0.46215(12) 0.63146(19) 0.0464(6) Uani 1 1 d . . . . .
C6 C 0.4745(3) 0.42164(13) 0.6087(2) 0.0505(7) Uani 1 1 d . . . . .
H6 H 0.369006 0.418866 0.654586 0.061 Uiso 1 1 calc R U . . .
C7 C 0.4849(3) 0.38411(11) 0.51283(19) 0.0429(6) Uani 1 1 d . . . . .
C8 C 0.2882(3) 0.26061(12) 0.3329(2) 0.0485(6) Uani 1 1 d . . . . .
H8A H 0.321188 0.256253 0.256594 0.058 Uiso 1 1 calc R U . . .
H8B H 0.158295 0.278179 0.336084 0.058 Uiso 1 1 calc R U . . .
C9 C 0.2892(3) 0.19111(12) 0.38389(19) 0.0419(6) Uani 1 1 d . . . . .
C10 C 0.1727(3) 0.14162(13) 0.3397(2) 0.0525(7) Uani 1 1 d . . . . .
H10 H 0.093470 0.151876 0.280591 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1716(4) 0.07731(13) 0.3815(3) 0.0605(8) Uani 1 1 d . . . . .
H11 H 0.092220 0.044927 0.350420 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2871(4) 0.06127(14) 0.4685(2) 0.0627(8) Uani 1 1 d . . . . .
H12 H 0.287830 0.017923 0.496097 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4009(4) 0.10923(15) 0.5142(2) 0.0702(9) Uani 1 1 d . . . . .
H13 H 0.478694 0.098559 0.573704 0.084 Uiso 1 1 calc R U . . .
C14 C 0.4022(4) 0.17410(14) 0.4728(2) 0.0598(7) Uani 1 1 d . . . . .
H14 H 0.480033 0.206385 0.505308 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7122(3) 0.31036(11) 0.26588(18) 0.0377(5) Uani 1 1 d . . . . .
C16 C 0.8082(3) 0.35228(12) 0.19226(19) 0.0429(6) Uani 1 1 d . . . . .
C17 C 0.9003(4) 0.32518(14) 0.1023(2) 0.0544(7) Uani 1 1 d . . . . .
H17 H 0.961562 0.353391 0.053330 0.065 Uiso 1 1 calc R U . . .
C18 C 0.9018(4) 0.25715(15) 0.0849(2) 0.0595(7) Uani 1 1 d . . . . .
H18 H 0.962165 0.239656 0.023803 0.071 Uiso 1 1 calc R U . . .
C19 C 0.8141(3) 0.21506(13) 0.1578(2) 0.0521(7) Uani 1 1 d . . . . .
H19 H 0.817097 0.168971 0.147190 0.063 Uiso 1 1 calc R U . . .
C20 C 0.7216(3) 0.24165(12) 0.24695(19) 0.0439(6) Uani 1 1 d . . . . .
H20 H 0.663531 0.212720 0.296092 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6476(4) 0.50369(15) 0.7322(2) 0.0640(8) Uani 1 1 d . . . . .
H21A H 0.748631 0.485452 0.776946 0.096 Uiso 1 1 calc R U . . .
H21B H 0.529334 0.503454 0.771931 0.096 Uiso 1 1 calc R U . . .
H21C H 0.679320 0.548811 0.712269 0.096 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 1.400(3) . ?
O1 C7 1.355(3) . ?
O2 C4 1.264(2) . ?
O4 H4 0.8200 . ?
O4 C16 1.367(3) . ?
N3 H3 0.8600 . ?
N3 C4 1.372(3) . ?
N3 C5 1.381(3) . ?
C1 C2 1.358(3) . ?
C1 C8 1.483(3) . ?
C2 C3 1.455(3) . ?
C2 C15 1.481(3) . ?
C3 C4 1.417(3) . ?
C3 C7 1.383(3) . ?
C5 C6 1.352(3) . ?
C5 C21 1.495(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(3) . ?
C9 C10 1.386(3) . ?
C9 C14 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.405(3) . ?
C15 C20 1.394(3) . ?
C16 C17 1.390(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C7 O1 C1 106.67(16) . . ?
C16 O4 H4 109.5 . . ?
C4 N3 H3 116.8 . . ?
C4 N3 C5 126.4(2) . . ?
C5 N3 H3 116.8 . . ?
O1 C1 C8 114.37(19) . . ?
C2 C1 O1 111.1(2) . . ?
C2 C1 C8 134.5(2) . . ?
C1 C2 C3 105.26(19) . . ?
C1 C2 C15 123.6(2) . . ?
C3 C2 C15 131.03(19) . . ?
C4 C3 C2 135.5(2) . . ?
C7 C3 C2 106.7(2) . . ?
C7 C3 C4 117.8(2) . . ?
O2 C4 N3 119.0(2) . . ?
O2 C4 C3 125.8(2) . . ?
N3 C4 C3 115.2(2) . . ?
N3 C5 C21 115.8(2) . . ?
C6 C5 N3 118.9(2) . . ?
C6 C5 C21 125.3(2) . . ?
C5 C6 H6 121.6 . . ?
C5 C6 C7 116.7(2) . . ?
C7 C6 H6 121.6 . . ?
O1 C7 C3 110.3(2) . . ?
O1 C7 C6 124.7(2) . . ?
C3 C7 C6 125.0(2) . . ?
C1 C8 H8A 108.3 . . ?
C1 C8 H8B 108.3 . . ?
C1 C8 C9 115.8(2) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C10 C9 C8 119.3(2) . . ?
C14 C9 C8 123.3(2) . . ?
C14 C9 C10 117.4(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 120.8(3) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C2 123.7(2) . . ?
C20 C15 C2 119.1(2) . . ?
C20 C15 C16 117.2(2) . . ?
O4 C16 C15 121.8(2) . . ?
O4 C16 C17 117.9(2) . . ?
C17 C16 C15 120.2(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 H20 118.9 . . ?
C19 C20 C15 122.3(2) . . ?
C19 C20 H20 118.9 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
_geom_hbond_publ_flag
O4 H4 O2 0.82 1.81 2.623(2) 170.4 . yes
N3 H3 O2 0.86 1.95 2.804(3) 172.3 3_766 yes

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 -1.1(2) . . . . ?
O1 C1 C2 C15 175.11(19) . . . . ?
O1 C1 C8 C9 -80.2(3) . . . . ?
O4 C16 C17 C18 -177.9(2) . . . . ?
N3 C5 C6 C7 1.3(4) . . . . ?
C1 O1 C7 C3 1.2(2) . . . . ?
C1 O1 C7 C6 -176.6(2) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
C1 C2 C3 C7 1.8(2) . . . . ?
C1 C2 C15 C16 135.8(2) . . . . ?
C1 C2 C15 C20 -40.8(3) . . . . ?
C1 C8 C9 C10 -178.7(2) . . . . ?
C1 C8 C9 C14 0.9(3) . . . . ?
C2 C1 C8 C9 101.5(3) . . . . ?
C2 C3 C4 O2 6.5(4) . . . . ?
C2 C3 C4 N3 -174.9(2) . . . . ?
C2 C3 C7 O1 -1.8(3) . . . . ?
C2 C3 C7 C6 175.9(2) . . . . ?
C2 C15 C16 O4 2.7(3) . . . . ?
C2 C15 C16 C17 -173.9(2) . . . . ?
C2 C15 C20 C19 174.4(2) . . . . ?
C3 C2 C15 C16 -49.0(3) . . . . ?
C3 C2 C15 C20 134.4(2) . . . . ?
C4 N3 C5 C6 -0.3(4) . . . . ?
C4 N3 C5 C21 177.8(2) . . . . ?
C4 C3 C7 O1 178.90(19) . . . . ?
C4 C3 C7 C6 -3.4(4) . . . . ?
C5 N3 C4 O2 176.2(2) . . . . ?
C5 N3 C4 C3 -2.4(3) . . . . ?
C5 C6 C7 O1 178.0(2) . . . . ?
C5 C6 C7 C3 0.6(4) . . . . ?
C7 O1 C1 C2 0.0(3) . . . . ?
C7 O1 C1 C8 -178.71(19) . . . . ?
C7 C3 C4 O2 -174.5(2) . . . . ?
C7 C3 C4 N3 4.0(3) . . . . ?
C8 C1 C2 C3 177.3(2) . . . . ?
C8 C1 C2 C15 -6.5(4) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C8 C9 C14 C13 -178.3(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C9 -0.5(5) . . . . ?
C14 C9 C10 C11 -1.1(4) . . . . ?
C15 C2 C3 C4 5.0(4) . . . . ?
C15 C2 C3 C7 -174.1(2) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C15 C20 C19 -2.5(3) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
C20 C15 C16 O4 179.4(2) . . . . ?
C20 C15 C16 C17 2.8(3) . . . . ?
C21 C5 C6 C7 -176.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_230523c_sq
_database_code_depnum_ccdc_archive 'CCDC 2295484'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2023-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O3, 0.25[C4H8O2]'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_formula_weight         331.36
_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'
N N 0.0061 0.0033 '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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   23.118(12)
_cell_length_b                   23.118(12)
_cell_length_c                   14.243(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7612(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      19.468
_cell_measurement_theta_min      2.432
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.7993.
The λ/2 correction factor is Not present.
;
_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    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1790
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.750
_diffrn_reflns_theta_max         24.750
_diffrn_reflns_theta_min         1.679
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1300
_reflns_number_total             3248
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractrometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     320
_refine_ls_R_factor_all          0.2022
_refine_ls_R_factor_gt           0.0862
_refine_ls_restrained_S_all      0.970
_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)+(0.1055P)²+9.2012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1958
_refine_ls_wR_factor_ref         0.2671
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8-C15A \\sim C8-C15
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C15 \\sim C17 \\sim C19 \\sim C18 \\sim C20 \\sim C16 \\sim C15A \\sim C17A
\\sim C19A \\sim C18A \\sim C21A \\sim C20A \\sim C16A \\sim C21: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C15, C8, C17, C19, C18, C21, C20, C16, C15A, C17A, C19A, C18A, C21A, C20A, C16A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7)
6.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C3(H3), C11(H11), C15A(H15A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A)
6.c Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C21), C16A(C17A,C18A,C19A,C20A,C21A)
6.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.e Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_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
C15 C 0.2949(9) 0.5167(6) 0.797(5) 0.084(3) Uani 0.524(19) 1 d D U P A 1
H15 H 0.255302 0.509732 0.799618 0.101 Uiso 0.524(19) 1 calc R U P A 1
O1 O 0.44749(18) 0.31601(15) 0.7464(3) 0.0801(11) Uani 1 1 d . . . . .
O3 O 0.38791(17) 0.47673(16) 0.8003(2) 0.0767(11) Uani 1 1 d . . . . .
O2 O 0.35732(17) 0.28333(17) 0.7341(3) 0.0937(14) Uani 1 1 d . . . . .
N1 N 0.2198(2) 0.32098(19) 0.7649(3) 0.0875(15) Uani 1 1 d . . . . .
H1A H 0.191866 0.296898 0.756908 0.105 Uiso 1 1 calc R U . . .
H1B H 0.239073 0.333361 0.717366 0.105 Uiso 1 1 calc R U . . .
C5 C 0.3707(2) 0.3814(2) 0.7759(3) 0.0593(13) Uani 1 1 d . . . . .
C7 C 0.3108(2) 0.4059(2) 0.7875(4) 0.0646(15) Uani 1 1 d . . . . .
H7 H 0.288830 0.400000 0.729389 0.078 Uiso 1 1 calc R U . . .
C8 C 0.3268(3) 0.4697(2) 0.7966(4) 0.0712(15) Uani 1 1 d D . . . .
C10 C 0.2337(2) 0.3398(2) 0.8542(4) 0.0705(15) Uani 1 1 d . . . . .
C6 C 0.3878(3) 0.3247(3) 0.7518(4) 0.0743(16) Uani 1 1 d . . . . .
C14 C 0.2904(3) 0.3974(2) 0.9614(4) 0.0824(17) Uani 1 1 d . . . . .
H14 H 0.320580 0.423246 0.971292 0.099 Uiso 1 1 calc R U . . .
C4 C 0.4112(3) 0.4230(3) 0.7860(3) 0.0653(15) Uani 1 1 d . . . . .
C12 C 0.2150(4) 0.3375(4) 1.0217(6) 0.113(2) Uani 1 1 d . . . . .
H12 H 0.193531 0.323647 1.072155 0.135 Uiso 1 1 calc R U . . .
C2 C 0.4877(3) 0.3589(3) 0.7608(4) 0.0760(16) Uani 1 1 d . . . . .
C1 C 0.5476(3) 0.3369(3) 0.7484(5) 0.106(2) Uani 1 1 d . . . . .
H1C H 0.555281 0.307594 0.794421 0.159 Uiso 1 1 calc R U . . .
H1D H 0.574486 0.368162 0.755974 0.159 Uiso 1 1 calc R U . . .
H1E H 0.551599 0.320746 0.686611 0.159 Uiso 1 1 calc R U . . .
C13 C 0.2606(4) 0.3767(3) 1.0368(5) 0.109(2) Uani 1 1 d . . . . .
H13 H 0.270279 0.388353 1.097264 0.131 Uiso 1 1 calc R U . . .
C16 C 0.3105(8) 0.5792(4) 0.7938(16) 0.085(3) Uani 0.524(19) 1 d DG U P A 1
C17 C 0.2659(7) 0.6188(5) 0.8068(13) 0.091(3) Uani 0.524(19) 1 d G U P A 1
H17 H 0.228375 0.605735 0.817061 0.110 Uiso 0.524(19) 1 calc R U P A 1
C18 C 0.2774(7) 0.6778(5) 0.8043(11) 0.095(3) Uani 0.524(19) 1 d G U P A 1
H18 H 0.247550 0.704208 0.812996 0.114 Uiso 0.524(19) 1 calc R U P A 1
C19 C 0.3335(8) 0.6972(4) 0.7889(11) 0.095(3) Uani 0.524(19) 1 d G U P A 1
H19 H 0.341165 0.736713 0.787299 0.114 Uiso 0.524(19) 1 calc R U P A 1
C20 C 0.3781(7) 0.6577(6) 0.7760(12) 0.100(3) Uani 0.524(19) 1 d G U P A 1
H20 H 0.415606 0.670744 0.765668 0.120 Uiso 0.524(19) 1 calc R U P A 1
C21 C 0.3666(7) 0.5987(5) 0.7784(16) 0.095(3) Uani 0.524(19) 1 d G U P A 1
H21 H 0.396433 0.572270 0.769734 0.114 Uiso 0.524(19) 1 calc R U P A 1
C3 C 0.4714(3) 0.4129(3) 0.7816(4) 0.0774(17) Uani 1 1 d . . . . .
H3 H 0.498160 0.442124 0.792655 0.093 Uiso 1 1 calc R U . . .
C11 C 0.2025(3) 0.3198(3) 0.9317(5) 0.092(2) Uani 1 1 d . . . . .
H11 H 0.172330 0.293776 0.922224 0.111 Uiso 1 1 calc R U . . .
C9 C 0.2769(2) 0.3810(2) 0.8699(4) 0.0652(15) Uani 1 1 d . . . . .
C15A C 0.2891(10) 0.5120(6) 0.796(6) 0.083(3) Uani 0.476(19) 1 d D U P A 2
H15A H 0.250857 0.499804 0.792649 0.099 Uiso 0.476(19) 1 calc R U P A 2
C16A C 0.2960(8) 0.5760(5) 0.8013(18) 0.085(3) Uani 0.476(19) 1 d DG U P A 2
C17A C 0.2462(7) 0.6085(6) 0.8161(16) 0.091(3) Uani 0.476(19) 1 d G U P A 2
H17A H 0.210871 0.590059 0.824553 0.109 Uiso 0.476(19) 1 calc R U P A 2
C18A C 0.2493(8) 0.6685(6) 0.8182(12) 0.098(3) Uani 0.476(19) 1 d G U P A 2
H18A H 0.216042 0.690257 0.828047 0.117 Uiso 0.476(19) 1 calc R U P A 2
C19A C 0.3022(9) 0.6961(5) 0.8055(11) 0.092(3) Uani 0.476(19) 1 d G U P A 2
H19A H 0.304287 0.736238 0.806908 0.111 Uiso 0.476(19) 1 calc R U P A 2
C20A C 0.3520(8) 0.6636(6) 0.7907(13) 0.096(3) Uani 0.476(19) 1 d G U P A 2
H20A H 0.387361 0.682022 0.782276 0.115 Uiso 0.476(19) 1 calc R U P A 2
C21A C 0.3489(7) 0.6036(6) 0.7887(17) 0.093(3) Uani 0.476(19) 1 d G U P A 2
H21A H 0.382190 0.581824 0.778782 0.112 Uiso 0.476(19) 1 calc R U P A 2


_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
C15 H15 0.9300 . ?
C15 C8 1.316(12) . ?
C15 C16 1.490(13) . ?
O1 C6 1.397(6) . ?
O1 C2 1.375(6) . ?
O3 C8 1.422(6) . ?
O3 C4 1.369(6) . ?
O2 C6 1.215(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C10 1.382(7) . ?
C5 C7 1.504(7) . ?
C5 C6 1.411(7) . ?
C5 C4 1.351(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(7) . ?
C7 C9 1.523(7) . ?
C8 C15A 1.312(13) . ?
C10 C11 1.397(8) . ?
C10 C9 1.399(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.362(8) . ?
C14 C9 1.393(7) . ?
C4 C3 1.412(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.407(9) . ?
C12 C11 1.377(9) . ?
C2 C1 1.484(7) . ?
C2 C3 1.338(7) . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C13 H13 0.9300 . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.3900 . ?
C21 H21 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C15A H15A 0.9300 . ?
C15A C16A 1.490(12) . ?
C16A C17A 1.3900 . ?
C16A C21A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C19A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C20A 1.3900 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.3900 . ?
C21A H21A 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
C8 C15 H15 114.1 . . ?
C8 C15 C16 131.8(17) . . ?
C16 C15 H15 114.1 . . ?
C2 O1 C6 123.8(5) . . ?
C4 O3 C8 106.3(4) . . ?
H1A N1 H1B 120.0 . . ?
C10 N1 H1A 120.0 . . ?
C10 N1 H1B 120.0 . . ?
C6 C5 C7 129.3(5) . . ?
C4 C5 C7 111.1(5) . . ?
C4 C5 C6 119.5(5) . . ?
C5 C7 H7 109.4 . . ?
C5 C7 C8 98.6(4) . . ?
C5 C7 C9 114.6(4) . . ?
C8 C7 H7 109.4 . . ?
C9 C7 H7 109.4 . . ?
C9 C7 C8 115.1(4) . . ?
C15 C8 O3 117.5(11) . . ?
C15 C8 C7 131.5(11) . . ?
O3 C8 C7 110.9(5) . . ?
C15A C8 O3 125.1(11) . . ?
C15A C8 C7 124.0(12) . . ?
N1 C10 C11 120.2(6) . . ?
N1 C10 C9 121.8(5) . . ?
C11 C10 C9 117.9(6) . . ?
O1 C6 C5 115.1(5) . . ?
O2 C6 O1 116.6(5) . . ?
O2 C6 C5 128.3(6) . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C9 122.0(6) . . ?
C9 C14 H14 119.0 . . ?
O3 C4 C3 123.0(5) . . ?
C5 C4 O3 112.9(5) . . ?
C5 C4 C3 124.1(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(7) . . ?
O1 C2 C1 111.5(5) . . ?
C3 C2 O1 121.0(5) . . ?
C3 C2 C1 127.5(6) . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C17 C16 C15 117.0(11) . . ?
C17 C16 C21 120.0 . . ?
C21 C16 C15 123.0(11) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C4 C3 H3 121.9 . . ?
C2 C3 C4 116.3(5) . . ?
C2 C3 H3 121.9 . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 121.9(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C9 C7 120.1(5) . . ?
C14 C9 C7 120.2(5) . . ?
C14 C9 C10 119.6(5) . . ?
C8 C15A H15A 114.0 . . ?
C8 C15A C16A 132.1(18) . . ?
C16A C15A H15A 114.0 . . ?
C17A C16A C15A 117.1(12) . . ?
C17A C16A C21A 120.0 . . ?
C21A C16A C15A 122.9(12) . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C18A C19A C20A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C16A C21A H21A 120.0 . . ?
C20A C21A C16A 120.0 . . ?
C20A C21A H21A 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1A O2 0.86 2.18 2.999(6) 159.2 13_556 yes

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
C15 C16 C17 C18 -180(3) . . . . ?
C15 C16 C21 C20 180(3) . . . . ?
O1 C2 C3 C4 -1.2(8) . . . . ?
O3 C8 C15A C16A -1(10) . . . . ?
O3 C4 C3 C2 -175.5(5) . . . . ?
N1 C10 C11 C12 180.0(6) . . . . ?
N1 C10 C9 C7 -0.8(7) . . . . ?
N1 C10 C9 C14 -178.3(5) . . . . ?
C5 C7 C8 C15 170(4) . . . . ?
C5 C7 C8 O3 -6.1(5) . . . . ?
C5 C7 C8 C15A 171(4) . . . . ?
C5 C7 C9 C10 -102.9(5) . . . . ?
C5 C7 C9 C14 74.5(6) . . . . ?
C5 C4 C3 C2 4.0(8) . . . . ?
C7 C5 C6 O1 179.8(4) . . . . ?
C7 C5 C6 O2 0.9(10) . . . . ?
C7 C5 C4 O3 -2.4(6) . . . . ?
C7 C5 C4 C3 178.0(5) . . . . ?
C7 C8 C15A C16A -178(5) . . . . ?
C8 C15 C16 C17 -172(5) . . . . ?
C8 C15 C16 C21 8(8) . . . . ?
C8 O3 C4 C5 -1.7(5) . . . . ?
C8 O3 C4 C3 177.8(5) . . . . ?
C8 C7 C9 C10 143.9(5) . . . . ?
C8 C7 C9 C14 -38.7(7) . . . . ?
C8 C15A C16A C17A -169(6) . . . . ?
C8 C15A C16A C21A 13(9) . . . . ?
C6 O1 C2 C1 -178.8(5) . . . . ?
C6 O1 C2 C3 0.2(8) . . . . ?
C6 C5 C7 C8 -171.0(5) . . . . ?
C6 C5 C7 C9 66.3(7) . . . . ?
C6 C5 C4 O3 174.0(4) . . . . ?
C6 C5 C4 C3 -5.5(8) . . . . ?
C4 O3 C8 C15 -172(4) . . . . ?
C4 O3 C8 C7 5.1(5) . . . . ?
C4 O3 C8 C15A -172(4) . . . . ?
C4 C5 C7 C8 5.0(5) . . . . ?
C4 C5 C7 C9 -117.7(5) . . . . ?
C4 C5 C6 O1 4.0(7) . . . . ?
C4 C5 C6 O2 -174.8(6) . . . . ?
C2 O1 C6 O2 177.4(5) . . . . ?
C2 O1 C6 C5 -1.6(7) . . . . ?
C1 C2 C3 C4 177.6(5) . . . . ?
C13 C14 C9 C7 179.1(5) . . . . ?
C13 C14 C9 C10 -3.4(9) . . . . ?
C13 C12 C11 C10 -0.2(10) . . . . ?
C16 C15 C8 O3 5(8) . . . . ?
C16 C15 C8 C7 -171(4) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C11 C10 C9 C7 -177.8(5) . . . . ?
C11 C10 C9 C14 4.7(8) . . . . ?
C11 C12 C13 C14 1.6(10) . . . . ?
C9 C7 C8 C15 -67(4) . . . . ?
C9 C7 C8 O3 116.3(5) . . . . ?
C9 C7 C8 C15A -67(4) . . . . ?
C9 C10 C11 C12 -3.0(9) . . . . ?
C9 C14 C13 C12 0.2(10) . . . . ?
C15A C16A C17A C18A -178(3) . . . . ?
C15A C16A C21A C20A 178(3) . . . . ?
C16A C17A C18A C19A 0.0 . . . . ?
C17A C16A C21A C20A 0.0 . . . . ?
C17A C18A C19A C20A 0.0 . . . . ?
C18A C19A C20A C21A 0.0 . . . . ?
C19A C20A C21A C16A 0.0 . . . . ?
C21A C16A C17A C18A 0.0 . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  
;
A solvent mask was calculated and 220 electrons were 
found in a volume of 1020Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.25[C4H8O2] per Asymmetric Unit 
which account for 192 electrons 
per unit cell.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.250 0.125 255 55 '1 C4H8O2'
2 0.000 0.750 0.875 255 55 '1 C4H8O2'
3 0.500 0.250 0.375 255 55 '1 C4H8O2'
4 0.500 0.750 0.625 255 55 '1 C4H8O2'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
