# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rpr028
_database_code_depnum_ccdc_archive 'CCDC 2302490'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N O3'
_chemical_formula_sum            'C26 H23 N O3'
_chemical_formula_weight         397.45

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.2675(3)
_cell_length_b                   11.2675(3)
_cell_length_c                   13.8644(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1524.36(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      79.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             630
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.677
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8456
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18707
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.531
_diffrn_reflns_theta_max         79.521
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4246
_reflns_number_gt                4205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_max     0.937
_reflns_Friedel_fraction_full    0.989

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.1444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0087(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2013 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4246
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.62636(13) 0.69383(13) 0.38709(9) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.59778(11) 0.62094(10) 0.59293(8) 0.0293(2) Uani 1 1 d . . . . .
O3 O 0.79671(13) 0.51421(13) 0.33840(8) 0.0360(3) Uani 1 1 d . . . . .
N N 0.85338(14) 0.79487(13) 0.43279(9) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.71627(16) 0.70284(15) 0.44043(11) 0.0275(3) Uani 1 1 d . . . . .
C2 C 0.69441(14) 0.61162(14) 0.52856(10) 0.0246(3) Uani 1 1 d . . . . .
C3 C 0.62835(14) 0.45664(14) 0.50051(10) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.576757 0.440571 0.438694 0.031 Uiso 1 1 calc R U . . .
C4 C 0.52727(14) 0.39118(15) 0.58180(11) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.51493(14) 0.49228(15) 0.63009(11) 0.0276(3) Uani 1 1 d . . . . .
C6 C 0.42785(17) 0.46473(18) 0.70745(12) 0.0347(3) Uani 1 1 d . . . . .
H6 H 0.420312 0.535345 0.739275 0.042 Uiso 1 1 calc R U . . .
C7 C 0.35143(17) 0.32823(19) 0.73669(13) 0.0386(4) Uani 1 1 d . . . . .
H7 H 0.290188 0.305170 0.789603 0.046 Uiso 1 1 calc R U . . .
C8 C 0.36295(16) 0.22568(18) 0.69022(14) 0.0376(4) Uani 1 1 d . . . . .
H8 H 0.310152 0.133649 0.711883 0.045 Uiso 1 1 calc R U . . .
C9 C 0.45147(15) 0.25620(16) 0.61178(12) 0.0317(3) Uani 1 1 d . . . . .
H9 H 0.459434 0.185959 0.579766 0.038 Uiso 1 1 calc R U . . .
C11 C 0.9386(2) 0.83508(18) 0.26407(13) 0.0424(4) Uani 1 1 d . . . . .
H11A H 0.959288 0.897909 0.209619 0.064 Uiso 1 1 calc R U . . .
H11B H 0.860556 0.745208 0.247596 0.064 Uiso 1 1 calc R U . . .
H11C H 1.018673 0.825611 0.278222 0.064 Uiso 1 1 calc R U . . .
C12 C 0.90334(19) 0.89168(16) 0.35206(12) 0.0363(4) Uani 1 1 d . . . . .
H12A H 0.985891 0.977180 0.372834 0.044 Uiso 1 1 calc R U . . .
H12B H 0.832256 0.914873 0.334265 0.044 Uiso 1 1 calc R U . . .
C13 C 0.92760(15) 0.77939(14) 0.50990(11) 0.0270(3) Uani 1 1 d . . . . .
C14 C 0.83499(15) 0.67574(14) 0.57129(10) 0.0257(3) Uani 1 1 d . . . . .
C15 C 0.87676(17) 0.64373(16) 0.65609(12) 0.0321(3) Uani 1 1 d . . . . .
H15 H 0.812346 0.574222 0.697572 0.039 Uiso 1 1 calc R U . . .
C16 C 1.01521(19) 0.71549(19) 0.67942(14) 0.0409(4) Uani 1 1 d . . . . .
H16 H 1.046693 0.696763 0.737902 0.049 Uiso 1 1 calc R U . . .
C17 C 1.10671(17) 0.81437(19) 0.61675(15) 0.0414(4) Uani 1 1 d . . . . .
H17 H 1.201252 0.860706 0.633091 0.050 Uiso 1 1 calc R U . . .
C18 C 1.06770(17) 0.84999(16) 0.53053(13) 0.0357(3) Uani 1 1 d . . . . .
C19 C 1.1772(2) 0.9584(2) 0.46746(17) 0.0547(5) Uani 1 1 d . . . . .
H19A H 1.161158 0.927574 0.400197 0.082 Uiso 1 1 calc R U . . .
H19B H 1.267292 0.974519 0.488054 0.082 Uiso 1 1 calc R U . . .
H19C H 1.174403 1.043679 0.473135 0.082 Uiso 1 1 calc R U . . .
C21 C 0.72919(16) 0.40357(15) 0.48982(11) 0.0295(3) Uani 1 1 d . . . . .
H21A H 0.778044 0.415836 0.551619 0.035 Uiso 1 1 calc R U . . .
H21B H 0.677728 0.304353 0.474980 0.035 Uiso 1 1 calc R U . . .
C22 C 0.83272(16) 0.47839(14) 0.41051(10) 0.0280(3) Uani 1 1 d . . . . .
C23 C 0.97756(16) 0.50859(15) 0.42055(11) 0.0289(3) Uani 1 1 d . . . . .
C24 C 1.02600(17) 0.47165(16) 0.50078(12) 0.0328(3) Uani 1 1 d . . . . .
H24 H 0.965018 0.421630 0.551779 0.039 Uiso 1 1 calc R U . . .
C25 C 1.16359(19) 0.50764(19) 0.50679(14) 0.0389(4) Uani 1 1 d . . . . .
H25 H 1.195805 0.481182 0.561416 0.047 Uiso 1 1 calc R U . . .
C26 C 1.25318(18) 0.58189(19) 0.43318(15) 0.0416(4) Uani 1 1 d . . . . .
H26 H 1.347165 0.607613 0.437737 0.050 Uiso 1 1 calc R U . . .
C27 C 1.2057(2) 0.61871(19) 0.35279(14) 0.0434(4) Uani 1 1 d . . . . .
H27 H 1.267259 0.669525 0.302260 0.052 Uiso 1 1 calc R U . . .
C28 C 1.06908(19) 0.58170(18) 0.34594(13) 0.0372(4) Uani 1 1 d . . . . .
H28 H 1.036991 0.606036 0.290193 0.045 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 1.217(2) . ?
O2 C5 1.3731(18) . ?
O2 C2 1.4516(17) . ?
O3 C22 1.221(2) . ?
N C1 1.368(2) . ?
N C13 1.421(2) . ?
N C12 1.4647(19) . ?
C1 C2 1.5351(19) . ?
C2 C14 1.496(2) . ?
C2 C3 1.5668(19) . ?
C3 C4 1.507(2) . ?
C3 C21 1.533(2) . ?
C4 C9 1.384(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.385(3) . ?
C8 C9 1.397(2) . ?
C11 C12 1.518(2) . ?
C13 C18 1.397(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.380(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.382(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.507(2) . ?
C21 C22 1.516(2) . ?
C22 C23 1.498(2) . ?
C23 C24 1.391(2) . ?
C23 C28 1.401(2) . ?
C24 C25 1.395(3) . ?
C25 C26 1.384(3) . ?
C26 C27 1.387(3) . ?
C27 C28 1.382(3) . ?

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
C5 O2 C2 107.03(11) . . ?
C1 N C13 111.08(12) . . ?
C1 N C12 119.44(14) . . ?
C13 N C12 129.48(14) . . ?
O1 C1 N 126.43(14) . . ?
O1 C1 C2 125.42(14) . . ?
N C1 C2 108.15(12) . . ?
O2 C2 C14 111.89(11) . . ?
O2 C2 C1 108.42(11) . . ?
C14 C2 C1 102.43(12) . . ?
O2 C2 C3 106.12(11) . . ?
C14 C2 C3 115.77(11) . . ?
C1 C2 C3 112.11(11) . . ?
C4 C3 C21 114.05(12) . . ?
C4 C3 C2 100.45(11) . . ?
C21 C3 C2 115.28(12) . . ?
C9 C4 C5 119.82(14) . . ?
C9 C4 C3 131.48(14) . . ?
C5 C4 C3 108.70(12) . . ?
O2 C5 C6 124.10(14) . . ?
O2 C5 C4 113.06(13) . . ?
C6 C5 C4 122.85(14) . . ?
C5 C6 C7 116.82(16) . . ?
C8 C7 C6 121.40(15) . . ?
C7 C8 C9 120.66(15) . . ?
C4 C9 C8 118.45(15) . . ?
N C12 C11 112.64(13) . . ?
C18 C13 C14 120.63(15) . . ?
C18 C13 N 130.63(14) . . ?
C14 C13 N 108.73(13) . . ?
C15 C14 C13 121.80(14) . . ?
C15 C14 C2 128.94(13) . . ?
C13 C14 C2 109.25(13) . . ?
C14 C15 C16 118.48(15) . . ?
C17 C16 C15 119.38(16) . . ?
C16 C17 C18 123.60(16) . . ?
C13 C18 C17 116.04(15) . . ?
C13 C18 C19 125.24(17) . . ?
C17 C18 C19 118.72(17) . . ?
C22 C21 C3 111.57(12) . . ?
O3 C22 C23 120.36(14) . . ?
O3 C22 C21 119.16(14) . . ?
C23 C22 C21 120.47(13) . . ?
C24 C23 C28 118.86(15) . . ?
C24 C23 C22 123.52(14) . . ?
C28 C23 C22 117.59(15) . . ?
C23 C24 C25 120.40(16) . . ?
C26 C25 C24 120.02(17) . . ?
C25 C26 C27 119.98(16) . . ?
C28 C27 C26 120.20(16) . . ?
C27 C28 C23 120.53(17) . . ?

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
C13 N C1 O1 177.56(14) . . . . ?
C12 N C1 O1 -2.2(2) . . . . ?
C13 N C1 C2 -2.46(15) . . . . ?
C12 N C1 C2 177.81(12) . . . . ?
C5 O2 C2 C14 -106.29(13) . . . . ?
C5 O2 C2 C1 141.48(12) . . . . ?
C5 O2 C2 C3 20.86(14) . . . . ?
O1 C1 C2 O2 -56.50(18) . . . . ?
N C1 C2 O2 123.53(12) . . . . ?
O1 C1 C2 C14 -174.91(14) . . . . ?
N C1 C2 C14 5.11(14) . . . . ?
O1 C1 C2 C3 60.33(18) . . . . ?
N C1 C2 C3 -119.65(13) . . . . ?
O2 C2 C3 C4 -20.42(14) . . . . ?
C14 C2 C3 C4 104.37(13) . . . . ?
C1 C2 C3 C4 -138.62(12) . . . . ?
O2 C2 C3 C21 -143.48(12) . . . . ?
C14 C2 C3 C21 -18.68(17) . . . . ?
C1 C2 C3 C21 98.32(14) . . . . ?
C21 C3 C4 C9 -43.2(2) . . . . ?
C2 C3 C4 C9 -167.08(15) . . . . ?
C21 C3 C4 C5 137.20(13) . . . . ?
C2 C3 C4 C5 13.29(14) . . . . ?
C2 O2 C5 C6 167.13(14) . . . . ?
C2 O2 C5 C4 -12.85(16) . . . . ?
C9 C4 C5 O2 179.13(13) . . . . ?
C3 C4 C5 O2 -1.19(17) . . . . ?
C9 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 C5 C6 178.82(14) . . . . ?
O2 C5 C6 C7 -179.48(15) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C3 C4 C9 C8 -179.05(15) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C1 N C12 C11 -89.15(19) . . . . ?
C13 N C12 C11 91.2(2) . . . . ?
C1 N C13 C18 179.70(15) . . . . ?
C12 N C13 C18 -0.6(2) . . . . ?
C1 N C13 C14 -1.50(16) . . . . ?
C12 N C13 C14 178.20(13) . . . . ?
C18 C13 C14 C15 3.1(2) . . . . ?
N C13 C14 C15 -175.84(13) . . . . ?
C18 C13 C14 C2 -176.13(13) . . . . ?
N C13 C14 C2 4.94(15) . . . . ?
O2 C2 C14 C15 58.87(19) . . . . ?
C1 C2 C14 C15 174.80(14) . . . . ?
C3 C2 C14 C15 -62.9(2) . . . . ?
O2 C2 C14 C13 -121.97(12) . . . . ?
C1 C2 C14 C13 -6.04(14) . . . . ?
C3 C2 C14 C13 116.26(13) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C2 C14 C15 C16 177.89(15) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C14 C13 C18 C17 -2.5(2) . . . . ?
N C13 C18 C17 176.14(15) . . . . ?
C14 C13 C18 C19 176.94(17) . . . . ?
N C13 C18 C19 -4.4(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C16 C17 C18 C19 -179.28(18) . . . . ?
C4 C3 C21 C22 -176.99(12) . . . . ?
C2 C3 C21 C22 -61.48(16) . . . . ?
C3 C21 C22 O3 -35.32(18) . . . . ?
C3 C21 C22 C23 144.43(13) . . . . ?
O3 C22 C23 C24 179.61(14) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
O3 C22 C23 C28 1.6(2) . . . . ?
C21 C22 C23 C28 -178.11(13) . . . . ?
C28 C23 C24 C25 0.3(2) . . . . ?
C22 C23 C24 C25 -177.61(15) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C23 1.0(3) . . . . ?
C24 C23 C28 C27 -1.2(2) . . . . ?
C22 C23 C28 C27 176.86(15) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.024



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, PE'
####################################################################### 
# 
# 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_rpr031
_database_code_depnum_ccdc_archive 'CCDC 2321099'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N O5, C H2 Cl2'
_chemical_formula_sum            'C27 H23 Cl2 N O5'
_chemical_formula_weight         512.36

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   18.3464(4)
_cell_length_b                   8.3122(2)
_cell_length_c                   16.0948(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.9900(10)
_cell_angle_gamma                90
_cell_volume                     2417.23(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      68.33

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    2.749
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7926
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26017
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4416
_reflns_number_gt                4021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+1.4899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     321
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.69132(6) 0.35873(13) 0.26945(6) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.78907(6) 0.41130(15) 0.20965(7) 0.0257(2) Uani 1 1 d . . . . .
O3 O 0.62893(6) 0.67413(14) 0.30517(7) 0.0245(2) Uani 1 1 d . . . . .
O4 O 0.74759(7) 0.26132(15) 0.55885(7) 0.0310(3) Uani 1 1 d D . . . .
H4O H 0.7570(13) 0.219(3) 0.6071(12) 0.038(6) Uiso 1 1 d D . . . .
O5 O 0.88965(6) 0.40723(16) 0.44038(8) 0.0337(3) Uani 1 1 d . . . . .
N N 0.54369(7) 0.49369(16) 0.34080(8) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.54422(8) 0.32926(18) 0.36339(8) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.48487(8) 0.2351(2) 0.37530(10) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.436348 0.278313 0.369981 0.028 Uiso 1 1 calc R U . . .
C3 C 0.49929(9) 0.0738(2) 0.39546(11) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.459593 0.005526 0.403584 0.034 Uiso 1 1 calc R U . . .
C4 C 0.57019(10) 0.0104(2) 0.40395(11) 0.0301(4) Uani 1 1 d . . . . .
H4 H 0.578499 -0.099650 0.418455 0.036 Uiso 1 1 calc R U . . .
C5 C 0.62932(9) 0.1075(2) 0.39130(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.678010 0.064996 0.397151 0.030 Uiso 1 1 calc R U . . .
C6 C 0.61544(8) 0.26675(18) 0.37010(9) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.66527(8) 0.39686(18) 0.34834(8) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.73760(7) 0.43105(17) 0.41012(8) 0.0157(3) Uani 1 1 d . . . . .
H8 H 0.761363 0.324536 0.425899 0.019 Uiso 1 1 calc R U . . .
C9 C 0.78413(7) 0.51427(17) 0.35213(8) 0.0162(3) Uani 1 1 d . . . . .
H9 H 0.769851 0.630301 0.345739 0.019 Uiso 1 1 calc R U . . .
C10 C 0.75808(8) 0.42675(18) 0.26916(9) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.61196(8) 0.54248(18) 0.32882(8) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.47787(8) 0.5961(2) 0.32816(10) 0.0243(3) Uani 1 1 d . . . . .
H12A H 0.436969 0.539217 0.291539 0.029 Uiso 1 1 calc R U . . .
H12B H 0.488471 0.695745 0.298768 0.029 Uiso 1 1 calc R U . . .
C13 C 0.45343(9) 0.6402(2) 0.41048(11) 0.0268(3) Uani 1 1 d . . . . .
H13A H 0.411650 0.715181 0.399260 0.040 Uiso 1 1 calc R U . . .
H13B H 0.494615 0.691245 0.448213 0.040 Uiso 1 1 calc R U . . .
H13C H 0.438226 0.542775 0.437202 0.040 Uiso 1 1 calc R U . . .
C21 C 0.72948(7) 0.51430(18) 0.49151(9) 0.0179(3) Uani 1 1 d . . . . .
C22 C 0.73567(8) 0.4223(2) 0.56502(9) 0.0217(3) Uani 1 1 d . . . . .
C23 C 0.72873(9) 0.4946(2) 0.64150(10) 0.0289(4) Uani 1 1 d . . . . .
H23 H 0.732776 0.431347 0.691239 0.035 Uiso 1 1 calc R U . . .
C24 C 0.71600(9) 0.6582(2) 0.64501(10) 0.0314(4) Uani 1 1 d . . . . .
H24 H 0.710999 0.706777 0.697147 0.038 Uiso 1 1 calc R U . . .
C25 C 0.71048(10) 0.7516(2) 0.57293(11) 0.0311(4) Uani 1 1 d . . . . .
H25 H 0.702032 0.864067 0.575495 0.037 Uiso 1 1 calc R U . . .
C26 C 0.71739(9) 0.6793(2) 0.49681(10) 0.0243(3) Uani 1 1 d . . . . .
H26 H 0.713817 0.743548 0.447458 0.029 Uiso 1 1 calc R U . . .
C31 C 0.86774(8) 0.50073(18) 0.38354(9) 0.0196(3) Uani 1 1 d . . . . .
C32 C 0.91945(8) 0.60382(19) 0.34596(10) 0.0210(3) Uani 1 1 d . . . . .
C33 C 0.99380(9) 0.6069(2) 0.38544(11) 0.0287(4) Uani 1 1 d . . . . .
H33 H 1.009376 0.544416 0.434738 0.034 Uiso 1 1 calc R U . . .
C34 C 1.04446(10) 0.7000(3) 0.35322(14) 0.0389(4) Uani 1 1 d . . . . .
H34 H 1.094574 0.703271 0.380905 0.047 Uiso 1 1 calc R U . . .
C35 C 1.02231(11) 0.7885(3) 0.28067(15) 0.0445(5) Uani 1 1 d . . . . .
H35 H 1.057404 0.851891 0.258283 0.053 Uiso 1 1 calc R U . . .
C36 C 0.94900(11) 0.7854(2) 0.24019(13) 0.0396(4) Uani 1 1 d . . . . .
H36 H 0.934228 0.845433 0.189850 0.048 Uiso 1 1 calc R U . . .
C37 C 0.89742(9) 0.6948(2) 0.27325(11) 0.0270(3) Uani 1 1 d . . . . .
H37 H 0.847056 0.694781 0.246348 0.032 Uiso 1 1 calc R U . . .
Cl1S Cl 0.89405(5) -0.10009(11) 0.51887(5) 0.0800(2) Uani 1 1 d . . . . .
Cl2S Cl 0.82542(4) 0.03204(10) 0.35662(5) 0.0756(3) Uani 1 1 d . . . . .
C1S C 0.90623(13) 0.0192(3) 0.43239(17) 0.0551(6) Uani 1 1 d . . . . .
H1SA H 0.921470 0.128732 0.452472 0.066 Uiso 1 1 calc R U . . .
H1SB H 0.946424 -0.026921 0.405992 0.066 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 C10 1.3497(18) . ?
O1 C7 1.4669(16) . ?
O2 C10 1.2025(19) . ?
O3 C11 1.217(2) . ?
O4 C22 1.362(2) . ?
O5 C31 1.214(2) . ?
N C11 1.3615(19) . ?
N C1 1.414(2) . ?
N C12 1.4624(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.393(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.388(3) . ?
C4 C5 1.395(2) . ?
C5 C6 1.379(2) . ?
C6 C7 1.496(2) . ?
C7 C8 1.5403(18) . ?
C7 C11 1.554(2) . ?
C8 C21 1.5115(19) . ?
C8 C9 1.5347(19) . ?
C9 C10 1.5230(19) . ?
C9 C31 1.5337(19) . ?
C12 C13 1.516(2) . ?
C21 C26 1.394(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.395(2) . ?
C23 C24 1.382(3) . ?
C24 C25 1.385(3) . ?
C25 C26 1.390(2) . ?
C31 C32 1.483(2) . ?
C32 C37 1.393(2) . ?
C32 C33 1.402(2) . ?
C33 C34 1.378(3) . ?
C34 C35 1.380(3) . ?
C35 C36 1.389(3) . ?
C36 C37 1.386(3) . ?
Cl1S C1S 1.755(3) . ?
Cl2S C1S 1.752(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C7 110.16(10) . . ?
C11 N C1 111.03(12) . . ?
C11 N C12 124.38(13) . . ?
C1 N C12 124.53(12) . . ?
C2 C1 C6 121.96(15) . . ?
C2 C1 N 127.82(14) . . ?
C6 C1 N 110.18(12) . . ?
C1 C2 C3 117.07(15) . . ?
C4 C3 C2 121.65(15) . . ?
C3 C4 C5 120.35(16) . . ?
C6 C5 C4 118.45(15) . . ?
C5 C6 C1 120.50(14) . . ?
C5 C6 C7 131.10(14) . . ?
C1 C6 C7 108.37(13) . . ?
O1 C7 C6 110.51(11) . . ?
O1 C7 C8 103.01(10) . . ?
C6 C7 C8 118.36(12) . . ?
O1 C7 C11 106.36(11) . . ?
C6 C7 C11 102.81(11) . . ?
C8 C7 C11 115.37(12) . . ?
C21 C8 C9 118.00(12) . . ?
C21 C8 C7 116.15(11) . . ?
C9 C8 C7 101.44(11) . . ?
C10 C9 C31 113.44(11) . . ?
C10 C9 C8 101.24(11) . . ?
C31 C9 C8 113.36(11) . . ?
O2 C10 O1 120.84(13) . . ?
O2 C10 C9 129.02(13) . . ?
O1 C10 C9 110.12(11) . . ?
O3 C11 N 127.14(14) . . ?
O3 C11 C7 125.28(13) . . ?
N C11 C7 107.55(12) . . ?
N C12 C13 112.43(13) . . ?
C26 C21 C22 118.49(14) . . ?
C26 C21 C8 122.96(13) . . ?
C22 C21 C8 118.53(13) . . ?
O4 C22 C23 121.86(15) . . ?
O4 C22 C21 117.81(13) . . ?
C23 C22 C21 120.33(15) . . ?
C24 C23 C22 120.12(16) . . ?
C23 C24 C25 120.36(15) . . ?
C24 C25 C26 119.44(17) . . ?
C25 C26 C21 121.26(16) . . ?
O5 C31 C32 121.70(14) . . ?
O5 C31 C9 118.47(13) . . ?
C32 C31 C9 119.81(13) . . ?
C37 C32 C33 119.24(15) . . ?
C37 C32 C31 122.92(14) . . ?
C33 C32 C31 117.83(14) . . ?
C34 C33 C32 120.44(17) . . ?
C33 C34 C35 119.92(17) . . ?
C34 C35 C36 120.39(17) . . ?
C37 C36 C35 119.99(18) . . ?
C36 C37 C32 119.98(16) . . ?
Cl2S C1S Cl1S 112.20(15) . . ?

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
C11 N C1 C2 -175.52(14) . . . . ?
C12 N C1 C2 1.9(2) . . . . ?
C11 N C1 C6 2.38(16) . . . . ?
C12 N C1 C6 179.77(13) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
N C1 C2 C3 178.41(14) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C4 C5 C6 C7 -176.34(15) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N C1 C6 C5 -179.77(13) . . . . ?
C2 C1 C6 C7 176.48(13) . . . . ?
N C1 C6 C7 -1.57(15) . . . . ?
C10 O1 C7 C6 -151.73(12) . . . . ?
C10 O1 C7 C8 -24.36(14) . . . . ?
C10 O1 C7 C11 97.38(13) . . . . ?
C5 C6 C7 O1 65.08(19) . . . . ?
C1 C6 C7 O1 -112.86(13) . . . . ?
C5 C6 C7 C8 -53.3(2) . . . . ?
C1 C6 C7 C8 128.78(13) . . . . ?
C5 C6 C7 C11 178.25(15) . . . . ?
C1 C6 C7 C11 0.31(14) . . . . ?
O1 C7 C8 C21 165.24(12) . . . . ?
C6 C7 C8 C21 -72.53(17) . . . . ?
C11 C7 C8 C21 49.81(17) . . . . ?
O1 C7 C8 C9 35.97(13) . . . . ?
C6 C7 C8 C9 158.21(12) . . . . ?
C11 C7 C8 C9 -79.46(13) . . . . ?
C21 C8 C9 C10 -162.08(12) . . . . ?
C7 C8 C9 C10 -34.00(13) . . . . ?
C21 C8 C9 C31 76.08(16) . . . . ?
C7 C8 C9 C31 -155.84(12) . . . . ?
C7 O1 C10 O2 -179.34(14) . . . . ?
C7 O1 C10 C9 1.98(15) . . . . ?
C31 C9 C10 O2 -35.6(2) . . . . ?
C8 C9 C10 O2 -157.37(16) . . . . ?
C31 C9 C10 O1 142.95(12) . . . . ?
C8 C9 C10 O1 21.17(15) . . . . ?
C1 N C11 O3 176.22(14) . . . . ?
C12 N C11 O3 -1.2(2) . . . . ?
C1 N C11 C7 -2.09(15) . . . . ?
C12 N C11 C7 -179.49(12) . . . . ?
O1 C7 C11 O3 -61.08(17) . . . . ?
C6 C7 C11 O3 -177.27(13) . . . . ?
C8 C7 C11 O3 52.41(19) . . . . ?
O1 C7 C11 N 117.27(12) . . . . ?
C6 C7 C11 N 1.08(14) . . . . ?
C8 C7 C11 N -129.24(12) . . . . ?
C11 N C12 C13 -109.52(16) . . . . ?
C1 N C12 C13 73.43(18) . . . . ?
C9 C8 C21 C26 42.01(19) . . . . ?
C7 C8 C21 C26 -78.73(18) . . . . ?
C9 C8 C21 C22 -136.83(14) . . . . ?
C7 C8 C21 C22 102.42(15) . . . . ?
C26 C21 C22 O4 -179.90(14) . . . . ?
C8 C21 C22 O4 -1.0(2) . . . . ?
C26 C21 C22 C23 0.9(2) . . . . ?
C8 C21 C22 C23 179.82(13) . . . . ?
O4 C22 C23 C24 -179.42(15) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C21 0.3(2) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C8 C21 C26 C25 -179.78(14) . . . . ?
C10 C9 C31 O5 -102.73(16) . . . . ?
C8 C9 C31 O5 12.0(2) . . . . ?
C10 C9 C31 C32 78.87(17) . . . . ?
C8 C9 C31 C32 -166.38(13) . . . . ?
O5 C31 C32 C37 170.56(16) . . . . ?
C9 C31 C32 C37 -11.1(2) . . . . ?
O5 C31 C32 C33 -8.6(2) . . . . ?
C9 C31 C32 C33 169.77(14) . . . . ?
C37 C32 C33 C34 0.6(3) . . . . ?
C31 C32 C33 C34 179.76(16) . . . . ?
C32 C33 C34 C35 -1.3(3) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C34 C35 C36 C37 0.9(3) . . . . ?
C35 C36 C37 C32 -1.5(3) . . . . ?
C33 C32 C37 C36 0.8(3) . . . . ?
C31 C32 C37 C36 -178.32(16) . . . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
