# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_a-28
_database_code_depnum_ccdc_archive 'CCDC 2117472'
loop_
_audit_author_name
_audit_author_address
tfg
;sd
China
;
_audit_update_record             
;
2021-10-23 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-07-16
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 Cl N2 O6'
_chemical_formula_sum            'C24 H23 Cl N2 O6'
_chemical_formula_weight         470.89
_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'
Cl Cl 0.1484 0.1585 '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      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                   7.0463(4)
_cell_length_b                   10.8325(7)
_cell_length_c                   15.8212(15)
_cell_angle_alpha                92.200(7)
_cell_angle_beta                 101.856(7)
_cell_angle_gamma                108.128(6)
_cell_volume                     1116.38(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.6550
_cell_measurement_theta_min      2.2830
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3934
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  18.00   1.00    3.00    --  -11.27 -77.00   0.00   95
  2  ω    -54.00  36.00   1.00    3.00    --   11.90 -57.00 120.00   90
  3  ω    -14.00  85.00   1.00    3.00    --   11.90  57.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0408154000
_diffrn_orient_matrix_UB_12      -0.0323143000
_diffrn_orient_matrix_UB_13      -0.0428104000
_diffrn_orient_matrix_UB_21      0.0522835000
_diffrn_orient_matrix_UB_22      0.0574110000
_diffrn_orient_matrix_UB_23      -0.0167674000
_diffrn_orient_matrix_UB_31      0.0862554000
_diffrn_orient_matrix_UB_32      -0.0215636000
_diffrn_orient_matrix_UB_33      0.0032153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3000
_reflns_number_total             3934
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0883
_refine_ls_restrained_S_all      1.042
_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)+(0.0722P)²+5.3105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2447
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.690(7)
 0.310(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C14(H14), C16(H16),
  C17(H17)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.4683(2) -0.08211(14) 0.64938(9) 0.0260(4) Uani 1 1 d . . . . .
O1 O -0.1404(6) 0.1852(4) 0.5684(3) 0.0236(9) Uani 1 1 d . . . . .
H1 H -0.133186 0.221147 0.523937 0.035 Uiso 1 1 calc R U . . .
O2 O 0.0282(5) 0.2769(4) 0.4442(2) 0.0199(8) Uani 1 1 d . . . . .
O3 O 0.9095(5) 0.5206(4) 0.3886(2) 0.0182(8) Uani 1 1 d . . . . .
O4 O 0.2838(8) 0.7168(5) 0.1515(3) 0.0415(13) Uani 1 1 d . . . . .
O5 O 0.6555(7) 0.2843(5) 0.0784(2) 0.0332(11) Uani 1 1 d . . . . .
O6 O 0.9280(6) 0.2612(4) 0.1753(2) 0.0222(9) Uani 1 1 d . . . . .
N1 N 0.7355(6) 0.4155(4) 0.4848(3) 0.0144(9) Uani 1 1 d . . . . .
H1A H 0.849772 0.433751 0.522620 0.017 Uiso 1 1 calc R U . . .
N2 N 0.7727(7) 0.3967(4) 0.2136(3) 0.0187(10) Uani 1 1 d . . . . .
H2 H 0.850825 0.402007 0.263992 0.022 Uiso 1 1 calc R U . . .
C1 C 0.1762(8) 0.1598(5) 0.5458(3) 0.0168(11) Uani 1 1 d . . . . .
C2 C 0.0147(8) 0.1357(5) 0.5888(3) 0.0170(11) Uani 1 1 d . . . . .
C3 C 0.0108(8) 0.0574(6) 0.6575(4) 0.0220(12) Uani 1 1 d . . . . .
H3 H -0.087903 0.048245 0.689950 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1547(8) -0.0062(5) 0.6768(3) 0.0204(12) Uani 1 1 d . . . . .
H4 H 0.151684 -0.059441 0.721558 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3027(8) 0.0098(5) 0.6290(4) 0.0192(11) Uani 1 1 d . . . . .
C6 C 0.3177(8) 0.0932(5) 0.5657(3) 0.0162(11) Uani 1 1 d . . . . .
H6 H 0.422090 0.105334 0.536107 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1829(8) 0.2511(5) 0.4781(3) 0.0155(11) Uani 1 1 d . . . . .
C8 C 0.3760(8) 0.3163(5) 0.4520(3) 0.0145(10) Uani 1 1 d . . . . .
C9 C 0.5628(8) 0.3465(5) 0.5079(3) 0.0146(11) Uani 1 1 d . . . . .
H9 H 0.571218 0.318967 0.563077 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3704(8) 0.3648(5) 0.3696(3) 0.0132(10) Uani 1 1 d . . . . .
H10 H 0.243951 0.348988 0.331311 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5446(8) 0.4338(5) 0.3447(3) 0.0148(11) Uani 1 1 d . . . . .
C12 C 0.7403(8) 0.4585(5) 0.4045(3) 0.0147(11) Uani 1 1 d . . . . .
C13 C 0.5366(8) 0.4944(5) 0.2617(3) 0.0162(11) Uani 1 1 d . . . . .
C14 C 0.4126(8) 0.5745(6) 0.2464(3) 0.0213(12) Uani 1 1 d . . . . .
H14 H 0.338548 0.585725 0.286729 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4001(9) 0.6371(6) 0.1711(4) 0.0255(13) Uani 1 1 d . . . . .
C16 C 0.5117(10) 0.6209(6) 0.1114(4) 0.0282(14) Uani 1 1 d . . . . .
H16 H 0.505845 0.663720 0.061600 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6310(9) 0.5413(6) 0.1259(4) 0.0239(12) Uani 1 1 d . . . . .
H17 H 0.703038 0.529482 0.084901 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6464(8) 0.4776(5) 0.2013(3) 0.0186(11) Uani 1 1 d . . . . .
C19 C 0.7746(8) 0.3114(6) 0.1487(3) 0.0201(12) Uani 1 1 d . . . . .
C20 C 0.9866(9) 0.1872(6) 0.1087(3) 0.0234(13) Uani 1 1 d . . . . .
C21 C 1.0543(11) 0.2767(7) 0.0410(4) 0.0369(16) Uani 1 1 d . . . . .
H21A H 0.937915 0.294424 0.007174 0.055 Uiso 1 1 calc R U . . .
H21B H 1.112839 0.234955 0.003573 0.055 Uiso 1 1 calc R U . . .
H21C H 1.154929 0.357289 0.069616 0.055 Uiso 1 1 calc R U . . .
C22 C 0.8102(10) 0.0626(7) 0.0702(4) 0.0371(16) Uani 1 1 d . . . . .
H22A H 0.763019 0.015766 0.116233 0.056 Uiso 1 1 calc R U . . .
H22B H 0.856507 0.008795 0.035116 0.056 Uiso 1 1 calc R U . . .
H22C H 0.699819 0.084666 0.034866 0.056 Uiso 1 1 calc R U . . .
C23 C 1.1686(9) 0.1558(6) 0.1615(4) 0.0273(13) Uani 1 1 d . . . . .
H23A H 1.276729 0.235630 0.185961 0.041 Uiso 1 1 calc R U . . .
H23B H 1.216706 0.105925 0.124396 0.041 Uiso 1 1 calc R U . . .
H23C H 1.127408 0.105961 0.207345 0.041 Uiso 1 1 calc R U . . .
C24 C 0.1762(11) 0.7417(7) 0.2132(4) 0.0358(16) Uani 1 1 d . . . . .
H24A H 0.098650 0.796909 0.190862 0.054 Uiso 1 1 calc R U . . .
H24B H 0.272396 0.784452 0.266344 0.054 Uiso 1 1 calc R U . . .
H24C H 0.084866 0.660605 0.224109 0.054 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
Cl1 C5 1.746(5) . ?
O1 H1 0.8200 . ?
O1 C2 1.349(6) . ?
O2 C7 1.231(6) . ?
O3 C12 1.255(6) . ?
O4 C15 1.366(7) . ?
O4 C24 1.419(8) . ?
O5 C19 1.211(7) . ?
O6 C19 1.355(6) . ?
O6 C20 1.497(6) . ?
N1 H1A 0.8600 . ?
N1 C9 1.345(7) . ?
N1 C12 1.373(6) . ?
N2 H2 0.8600 . ?
N2 C18 1.422(7) . ?
N2 C19 1.360(7) . ?
C1 C2 1.405(7) . ?
C1 C6 1.397(7) . ?
C1 C7 1.484(8) . ?
C2 C3 1.403(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(8) . ?
C5 C6 1.372(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.475(7) . ?
C8 C9 1.361(7) . ?
C8 C10 1.422(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.369(7) . ?
C11 C12 1.444(7) . ?
C11 C13 1.489(7) . ?
C13 C14 1.406(7) . ?
C13 C18 1.386(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(8) . ?
C15 C16 1.385(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(8) . ?
C20 C21 1.523(8) . ?
C20 C22 1.523(9) . ?
C20 C23 1.520(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C2 O1 H1 109.5 . . ?
C15 O4 C24 118.0(5) . . ?
C19 O6 C20 118.5(4) . . ?
C9 N1 H1A 118.0 . . ?
C9 N1 C12 124.0(4) . . ?
C12 N1 H1A 118.0 . . ?
C18 N2 H2 118.7 . . ?
C19 N2 H2 118.7 . . ?
C19 N2 C18 122.6(4) . . ?
C2 C1 C7 118.1(4) . . ?
C6 C1 C2 119.0(5) . . ?
C6 C1 C7 122.9(5) . . ?
O1 C2 C1 123.5(5) . . ?
O1 C2 C3 116.7(5) . . ?
C1 C2 C3 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 Cl1 118.2(4) . . ?
C6 C5 Cl1 120.4(4) . . ?
C6 C5 C4 121.4(5) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(5) . . ?
C5 C6 H6 120.0 . . ?
O2 C7 C1 120.5(5) . . ?
O2 C7 C8 118.5(5) . . ?
C8 C7 C1 120.9(4) . . ?
C9 C8 C7 122.4(5) . . ?
C9 C8 C10 117.2(5) . . ?
C10 C8 C7 119.9(4) . . ?
N1 C9 C8 121.3(5) . . ?
N1 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C10 H10 118.9 . . ?
C11 C10 C8 122.2(5) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C12 118.6(5) . . ?
C10 C11 C13 121.9(5) . . ?
C12 C11 C13 119.2(5) . . ?
O3 C12 N1 119.3(4) . . ?
O3 C12 C11 124.1(5) . . ?
N1 C12 C11 116.5(5) . . ?
C14 C13 C11 116.7(4) . . ?
C18 C13 C11 123.6(5) . . ?
C18 C13 C14 119.7(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.8 . . ?
O4 C15 C14 124.0(5) . . ?
O4 C15 C16 116.3(5) . . ?
C16 C15 C14 119.7(5) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(5) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 N2 121.7(5) . . ?
C13 C18 C17 119.0(5) . . ?
C17 C18 N2 119.3(5) . . ?
O5 C19 O6 125.7(5) . . ?
O5 C19 N2 124.7(5) . . ?
O6 C19 N2 109.6(4) . . ?
O6 C20 C21 109.0(5) . . ?
O6 C20 C22 110.1(5) . . ?
O6 C20 C23 102.9(4) . . ?
C22 C20 C21 113.4(5) . . ?
C23 C20 C21 110.0(5) . . ?
C23 C20 C22 111.0(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 H1 O2 0.82 1.86 2.576(5) 144.7 . yes
N1 H1A O3 0.86 1.88 2.740(5) 175.5 2_766 yes
N2 H2 O3 0.86 2.20 2.866(5) 133.9 . 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
Cl1 C5 C6 C1 175.7(4) . . . . ?
O1 C2 C3 C4 174.1(5) . . . . ?
O2 C7 C8 C9 147.8(5) . . . . ?
O2 C7 C8 C10 -24.2(7) . . . . ?
O4 C15 C16 C17 -179.4(6) . . . . ?
C1 C2 C3 C4 -6.4(8) . . . . ?
C1 C7 C8 C9 -30.1(7) . . . . ?
C1 C7 C8 C10 157.9(5) . . . . ?
C2 C1 C6 C5 -2.7(8) . . . . ?
C2 C1 C7 O2 -19.2(7) . . . . ?
C2 C1 C7 C8 158.7(5) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
C3 C4 C5 Cl1 -174.9(4) . . . . ?
C3 C4 C5 C6 3.6(8) . . . . ?
C4 C5 C6 C1 -2.8(8) . . . . ?
C6 C1 C2 O1 -173.4(5) . . . . ?
C6 C1 C2 C3 7.2(8) . . . . ?
C6 C1 C7 O2 158.0(5) . . . . ?
C6 C1 C7 C8 -24.2(7) . . . . ?
C7 C1 C2 O1 3.9(8) . . . . ?
C7 C1 C2 C3 -175.5(5) . . . . ?
C7 C1 C6 C5 -179.8(5) . . . . ?
C7 C8 C9 N1 -174.5(4) . . . . ?
C7 C8 C10 C11 175.5(4) . . . . ?
C8 C10 C11 C12 -0.3(7) . . . . ?
C8 C10 C11 C13 -174.4(4) . . . . ?
C9 N1 C12 O3 -178.9(5) . . . . ?
C9 N1 C12 C11 4.0(7) . . . . ?
C9 C8 C10 C11 3.0(7) . . . . ?
C10 C8 C9 N1 -2.3(7) . . . . ?
C10 C11 C12 O3 -180.0(5) . . . . ?
C10 C11 C12 N1 -3.1(7) . . . . ?
C10 C11 C13 C14 51.8(7) . . . . ?
C10 C11 C13 C18 -129.5(6) . . . . ?
C11 C13 C14 C15 178.6(5) . . . . ?
C11 C13 C18 N2 1.8(8) . . . . ?
C11 C13 C18 C17 -178.7(5) . . . . ?
C12 N1 C9 C8 -1.3(7) . . . . ?
C12 C11 C13 C14 -122.3(5) . . . . ?
C12 C11 C13 C18 56.4(7) . . . . ?
C13 C11 C12 O3 -5.7(7) . . . . ?
C13 C11 C12 N1 171.2(4) . . . . ?
C13 C14 C15 O4 -179.8(6) . . . . ?
C13 C14 C15 C16 -0.4(9) . . . . ?
C14 C13 C18 N2 -179.5(5) . . . . ?
C14 C13 C18 C17 0.0(8) . . . . ?
C14 C15 C16 C17 1.2(9) . . . . ?
C15 C16 C17 C18 -1.4(9) . . . . ?
C16 C17 C18 N2 -179.7(5) . . . . ?
C16 C17 C18 C13 0.8(9) . . . . ?
C18 N2 C19 O5 -8.9(9) . . . . ?
C18 N2 C19 O6 171.7(5) . . . . ?
C18 C13 C14 C15 -0.1(8) . . . . ?
C19 O6 C20 C21 59.5(6) . . . . ?
C19 O6 C20 C22 -65.4(7) . . . . ?
C19 O6 C20 C23 176.3(5) . . . . ?
C19 N2 C18 C13 136.1(6) . . . . ?
C19 N2 C18 C17 -43.4(8) . . . . ?
C20 O6 C19 O5 13.2(9) . . . . ?
C20 O6 C19 N2 -167.4(5) . . . . ?
C24 O4 C15 C14 2.8(9) . . . . ?
C24 O4 C15 C16 -176.6(6) . . . . ?

_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.578
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.690(7)
2 0.310(7)

####################################################################### 
# 
# 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_a-13_4
_database_code_depnum_ccdc_archive 'CCDC 2129667'
loop_
_audit_author_name
_audit_author_address
fgfg
;jii
China
;
_audit_update_record             
;
2021-12-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-07-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3858(3)
_cell_length_b                   25.0398(5)
_cell_length_c                   9.6706(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.796(3)
_cell_angle_gamma                90
_cell_volume                     2138.46(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.1070
_cell_measurement_theta_min      3.4600
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.285
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  78.00   1.00    1.00    --   40.73 -99.00  90.00   76
  2  ω     40.00  97.00   1.00    1.00    --  108.20-125.00  90.00   57
  3  ω     90.00 120.00   1.00    1.00    --  108.20-125.00   0.00   30
  4  ω     47.00 131.00   1.00    1.00    --  108.20 -45.00  60.00   84
  5  ω    143.00 176.00   1.00    1.00    --  108.20  45.00 150.00   33
  6  ω    132.00 167.00   1.00    1.00    --  108.20  45.00   0.00   35
  7  ω    131.00 177.00   1.00    1.00    --  108.20  45.00-120.00   46
  8  ω     83.00 117.00   1.00    1.00    --  108.20  45.00   0.00   34
  9  ω     87.00 114.00   1.00    1.00    --  108.20  45.00 150.00   27
 10  ω     36.00 139.00   1.00    1.00    --  108.20 -77.00-150.00  103
 11  ω     28.00  68.00   1.00    1.00    --   40.73  38.00-180.00   40
 12  ω   -117.00 -11.00   1.00    1.00    --  -40.73 -77.00-150.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1046590000
_diffrn_orient_matrix_UB_12      0.0299859000
_diffrn_orient_matrix_UB_13      0.1354054000
_diffrn_orient_matrix_UB_21      0.0428936000
_diffrn_orient_matrix_UB_22      -0.0533175000
_diffrn_orient_matrix_UB_23      0.0833381000
_diffrn_orient_matrix_UB_31      0.1327893000
_diffrn_orient_matrix_UB_32      -0.0064848000
_diffrn_orient_matrix_UB_33      -0.0583066000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3842
_reflns_number_total             4239
_reflns_odcompleteness_completeness 99.87
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.063
_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)+(0.0458P)²+0.7623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C2(H2B), C4(H4), C5(H5), C9(H9), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.65509(13) 0.67922(6) 0.25715(12) 0.0460(3) Uani 1 1 d . . . . .
O2 O 0.08287(11) 0.70711(4) 0.28559(11) 0.0314(2) Uani 1 1 d . . . . .
H2 H 0.030730 0.725179 0.216164 0.047 Uiso 1 1 calc R U . . .
O3 O 0.37916(13) 0.72032(5) 0.64740(12) 0.0354(3) Uani 1 1 d . . . . .
O4 O -0.01994(12) 0.52503(4) 0.66116(11) 0.0281(2) Uani 1 1 d . . . . .
O5 O 0.25367(13) 0.55997(5) 1.22026(11) 0.0354(3) Uani 1 1 d . . . . .
O6 O 0.32884(11) 0.49710(4) 1.08944(10) 0.0286(2) Uani 1 1 d . . . . .
N1 N 0.09273(13) 0.56544(4) 0.51528(12) 0.0222(2) Uani 1 1 d . . . . .
H1 H 0.072260 0.537943 0.458637 0.027 Uiso 1 1 calc R U . . .
N2 N 0.13028(13) 0.54700(5) 0.97479(12) 0.0256(3) Uani 1 1 d . . . . .
H2A H 0.128138 0.527528 0.900860 0.031 Uiso 1 1 calc R U . . .
C1 C 0.34173(15) 0.69096(5) 0.40469(14) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.48904(15) 0.68451(6) 0.40362(15) 0.0260(3) Uani 1 1 d . . . . .
H2B H 0.568806 0.679491 0.491267 0.031 Uiso 1 1 calc R U . . .
C3 C 0.51578(16) 0.68562(6) 0.27131(16) 0.0302(3) Uani 1 1 d . . . . .
C4 C 0.39506(18) 0.69374(6) 0.14036(16) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.412913 0.694342 0.051465 0.038 Uiso 1 1 calc R U . . .
C5 C 0.25013(16) 0.70084(6) 0.14172(15) 0.0283(3) Uani 1 1 d . . . . .
H5 H 0.170863 0.706552 0.054107 0.034 Uiso 1 1 calc R U . . .
C6 C 0.22208(15) 0.69949(5) 0.27406(15) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.31269(15) 0.69013(5) 0.54724(14) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.20668(14) 0.65033(5) 0.56818(14) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.14659(15) 0.65504(5) 0.68453(14) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.163970 0.686222 0.740020 0.026 Uiso 1 1 calc R U . . .
C10 C 0.06407(14) 0.61498(5) 0.71686(14) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.04153(15) 0.56578(5) 0.63316(14) 0.0217(3) Uani 1 1 d . . . . .
C12 C 0.17277(14) 0.60533(5) 0.48279(14) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.205003 0.602256 0.402180 0.026 Uiso 1 1 calc R U . . .
C13 C -0.01028(15) 0.62127(5) 0.82952(14) 0.0221(3) Uani 1 1 d . . . . .
C14 C 0.02082(15) 0.58771(5) 0.95210(14) 0.0233(3) Uani 1 1 d . . . . .
C15 C -0.05529(16) 0.59516(6) 1.05190(15) 0.0280(3) Uani 1 1 d . . . . .
H15 H -0.034998 0.572746 1.132987 0.034 Uiso 1 1 calc R U . . .
C16 C -0.16051(17) 0.63553(6) 1.03121(16) 0.0304(3) Uani 1 1 d . . . . .
H16 H -0.211292 0.639991 1.097966 0.036 Uiso 1 1 calc R U . . .
C17 C -0.19085(17) 0.66940(6) 0.91177(16) 0.0300(3) Uani 1 1 d . . . . .
H17 H -0.261339 0.696738 0.898328 0.036 Uiso 1 1 calc R U . . .
C18 C -0.11543(16) 0.66231(5) 0.81225(15) 0.0258(3) Uani 1 1 d . . . . .
H18 H -0.135288 0.685326 0.732464 0.031 Uiso 1 1 calc R U . . .
C19 C 0.23931(16) 0.53666(6) 1.10688(15) 0.0263(3) Uani 1 1 d . . . . .
C20 C 0.45859(16) 0.47871(6) 1.21650(15) 0.0307(3) Uani 1 1 d . . . . .
C21 C 0.40172(19) 0.45579(7) 1.33347(17) 0.0369(4) Uani 1 1 d . . . . .
H21A H 0.359255 0.483894 1.374783 0.055 Uiso 1 1 calc R U . . .
H21B H 0.484456 0.439581 1.409500 0.055 Uiso 1 1 calc R U . . .
H21C H 0.325474 0.429390 1.290125 0.055 Uiso 1 1 calc R U . . .
C22 C 0.57119(19) 0.52420(7) 1.27202(18) 0.0396(4) Uani 1 1 d . . . . .
H22A H 0.601316 0.537417 1.192891 0.059 Uiso 1 1 calc R U . . .
H22B H 0.658603 0.511410 1.349588 0.059 Uiso 1 1 calc R U . . .
H22C H 0.524637 0.552470 1.308599 0.059 Uiso 1 1 calc R U . . .
C23 C 0.52500(18) 0.43484(7) 1.14940(18) 0.0379(4) Uani 1 1 d . . . . .
H23A H 0.449642 0.407917 1.108504 0.057 Uiso 1 1 calc R U . . .
H23B H 0.610204 0.419211 1.223929 0.057 Uiso 1 1 calc R U . . .
H23C H 0.557295 0.449550 1.073221 0.057 Uiso 1 1 calc R U . . .
C24 C 0.77936(18) 0.67076(9) 0.38900(19) 0.0475(5) Uani 1 1 d . . . . .
H24A H 0.870637 0.666808 0.366072 0.071 Uiso 1 1 calc R U . . .
H24B H 0.762167 0.638983 0.436607 0.071 Uiso 1 1 calc R U . . .
H24C H 0.789130 0.700790 0.453284 0.071 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 C3 1.3694(18) . ?
O1 C24 1.423(2) . ?
O2 H2 0.8200 . ?
O2 C6 1.3618(17) . ?
O3 C7 1.2205(17) . ?
O4 C11 1.2463(16) . ?
O5 C19 1.2087(17) . ?
O6 C19 1.3460(17) . ?
O6 C20 1.4803(16) . ?
N1 H1 0.8600 . ?
N1 C11 1.3790(17) . ?
N1 C12 1.3494(17) . ?
N2 H2A 0.8600 . ?
N2 C14 1.4107(17) . ?
N2 C19 1.3641(18) . ?
C1 C2 1.3955(19) . ?
C1 C6 1.3935(18) . ?
C1 C7 1.4932(18) . ?
C2 H2B 0.9300 . ?
C2 C3 1.3852(19) . ?
C3 C4 1.399(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(2) . ?
C7 C8 1.4698(18) . ?
C8 C9 1.4240(18) . ?
C8 C12 1.3692(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3667(19) . ?
C10 C11 1.4498(18) . ?
C10 C13 1.4879(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.4008(19) . ?
C13 C18 1.3950(19) . ?
C14 C15 1.3940(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9300 . ?
C20 C21 1.518(2) . ?
C20 C22 1.523(2) . ?
C20 C23 1.513(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C3 O1 C24 116.66(12) . . ?
C6 O2 H2 109.5 . . ?
C19 O6 C20 119.86(11) . . ?
C11 N1 H1 117.8 . . ?
C12 N1 H1 117.8 . . ?
C12 N1 C11 124.42(11) . . ?
C14 N2 H2A 118.0 . . ?
C19 N2 H2A 118.0 . . ?
C19 N2 C14 123.97(11) . . ?
C2 C1 C7 119.75(12) . . ?
C6 C1 C2 120.49(12) . . ?
C6 C1 C7 119.74(12) . . ?
C1 C2 H2B 120.2 . . ?
C3 C2 C1 119.63(13) . . ?
C3 C2 H2B 120.2 . . ?
O1 C3 C2 124.60(13) . . ?
O1 C3 C4 115.76(13) . . ?
C2 C3 C4 119.64(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.68(13) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.07(13) . . ?
C6 C5 H5 120.0 . . ?
O2 C6 C1 116.63(12) . . ?
O2 C6 C5 123.88(12) . . ?
C5 C6 C1 119.47(13) . . ?
O3 C7 C1 121.33(12) . . ?
O3 C7 C8 119.90(12) . . ?
C8 C7 C1 118.71(11) . . ?
C9 C8 C7 121.36(12) . . ?
C12 C8 C7 120.31(12) . . ?
C12 C8 C9 118.12(12) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.79(12) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 118.87(12) . . ?
C9 C10 C13 122.18(12) . . ?
C11 C10 C13 118.87(12) . . ?
O4 C11 N1 119.41(12) . . ?
O4 C11 C10 124.42(12) . . ?
N1 C11 C10 116.16(11) . . ?
N1 C12 C8 120.19(12) . . ?
N1 C12 H12 119.9 . . ?
C8 C12 H12 119.9 . . ?
C14 C13 C10 122.77(12) . . ?
C18 C13 C10 118.59(12) . . ?
C18 C13 C14 118.65(12) . . ?
C13 C14 N2 119.81(12) . . ?
C15 C14 N2 120.39(12) . . ?
C15 C14 C13 119.80(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.46(13) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.36(13) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.50(13) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.22(13) . . ?
C17 C18 H18 119.4 . . ?
O5 C19 O6 125.91(13) . . ?
O5 C19 N2 125.15(13) . . ?
O6 C19 N2 108.94(11) . . ?
O6 C20 C21 109.77(12) . . ?
O6 C20 C22 109.73(12) . . ?
O6 C20 C23 102.27(11) . . ?
C21 C20 C22 113.42(13) . . ?
C23 C20 C21 110.18(14) . . ?
C23 C20 C22 110.90(13) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 -179.75(15) . . . . ?
O3 C7 C8 C9 17.7(2) . . . . ?
O3 C7 C8 C12 -156.96(13) . . . . ?
N2 C14 C15 C16 178.89(13) . . . . ?
C1 C2 C3 O1 -179.34(15) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C7 C8 C9 -164.97(12) . . . . ?
C1 C7 C8 C12 20.34(18) . . . . ?
C2 C1 C6 O2 -177.93(12) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C7 O3 55.32(19) . . . . ?
C2 C1 C7 C8 -121.93(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 O2 178.74(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C6 C1 C7 O3 -123.10(15) . . . . ?
C6 C1 C7 C8 59.65(17) . . . . ?
C7 C1 C2 C3 -179.61(13) . . . . ?
C7 C1 C6 O2 0.49(19) . . . . ?
C7 C1 C6 C5 179.26(12) . . . . ?
C7 C8 C9 C10 -171.30(12) . . . . ?
C7 C8 C12 N1 170.70(12) . . . . ?
C8 C9 C10 C11 2.00(19) . . . . ?
C8 C9 C10 C13 -174.64(12) . . . . ?
C9 C8 C12 N1 -4.17(19) . . . . ?
C9 C10 C11 O4 173.41(13) . . . . ?
C9 C10 C11 N1 -6.66(18) . . . . ?
C9 C10 C13 C14 -121.68(15) . . . . ?
C9 C10 C13 C18 58.35(18) . . . . ?
C10 C13 C14 N2 2.1(2) . . . . ?
C10 C13 C14 C15 -178.67(12) . . . . ?
C10 C13 C18 C17 178.53(13) . . . . ?
C11 N1 C12 C8 -0.9(2) . . . . ?
C11 C10 C13 C14 61.67(18) . . . . ?
C11 C10 C13 C18 -118.30(14) . . . . ?
C12 N1 C11 O4 -173.74(12) . . . . ?
C12 N1 C11 C10 6.33(19) . . . . ?
C12 C8 C9 C10 3.52(19) . . . . ?
C13 C10 C11 O4 -9.8(2) . . . . ?
C13 C10 C11 N1 170.09(11) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 N2 C19 O5 1.7(2) . . . . ?
C14 N2 C19 O6 -177.35(12) . . . . ?
C14 C13 C18 C17 -1.4(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C18 C13 C14 N2 -177.94(12) . . . . ?
C18 C13 C14 C15 1.3(2) . . . . ?
C19 O6 C20 C21 62.60(17) . . . . ?
C19 O6 C20 C22 -62.68(16) . . . . ?
C19 O6 C20 C23 179.55(13) . . . . ?
C19 N2 C14 C13 134.45(14) . . . . ?
C19 N2 C14 C15 -44.8(2) . . . . ?
C20 O6 C19 O5 0.0(2) . . . . ?
C20 O6 C19 N2 178.98(12) . . . . ?
C24 O1 C3 C2 0.2(3) . . . . ?
C24 O1 C3 C4 -179.83(16) . . . . ?

_olex2_date_sample_data_collection 2021-07-05
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.722
