# Electronic Supplementary Material (ESI) 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_zhk013
_database_code_depnum_ccdc_archive 'CCDC 2218552'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2022-11-09 deposited with the CCDC.	2024-06-05 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 O2, C2 H6 O S'
_chemical_formula_sum            'C28 H29 N O3 S'
_chemical_formula_weight         459.58

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'
S S 0.3331 0.5567 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7923(2)
_cell_length_b                   15.0923(3)
_cell_length_c                   14.4236(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.7170(10)
_cell_angle_gamma                90
_cell_volume                     2344.38(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      79.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    1.466
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.771
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_T_max  0.9801
_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            18421
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.244
_diffrn_reflns_theta_max         79.529
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4893
_reflns_number_gt                4340
_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)+(0.0645P)²+0.7803P] 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         4893
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.34462(11) 0.59484(8) 0.57857(8) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.52484(10) 0.77486(7) 0.84038(7) 0.0260(2) Uani 1 1 d . . . . .
N1 N 0.20189(11) 0.59708(8) 0.68989(9) 0.0260(3) Uani 1 1 d D . . . .
H1N H 0.1350(17) 0.6036(15) 0.6522(14) 0.043(6) Uiso 1 1 d D . . . .
C1 C 0.31767(14) 0.59121(9) 0.65945(10) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.41080(13) 0.58004(9) 0.74548(10) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.32720(13) 0.59525(9) 0.82428(10) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.20503(13) 0.60322(9) 0.78676(11) 0.0239(3) Uani 1 1 d . . . . .
C5 C 0.10621(14) 0.61788(10) 0.84143(12) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.023607 0.622971 0.814933 0.037 Uiso 1 1 calc R U . . .
C6 C 0.13298(16) 0.62482(11) 0.93671(13) 0.0368(4) Uani 1 1 d . . . . .
H6 H 0.067154 0.635002 0.976041 0.044 Uiso 1 1 calc R U . . .
C7 C 0.25304(17) 0.61729(12) 0.97574(12) 0.0357(4) Uani 1 1 d . . . . .
H7 H 0.268529 0.622475 1.041108 0.043 Uiso 1 1 calc R U . . .
C8 C 0.35200(15) 0.60206(10) 0.91940(11) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.434498 0.596511 0.945987 0.034 Uiso 1 1 calc R U . . .
C11 C 0.46277(13) 0.48474(9) 0.74239(11) 0.0263(3) Uani 1 1 d . . . . .
C12 C 0.45900(15) 0.42721(10) 0.81757(13) 0.0338(4) Uani 1 1 d . . . . .
H12 H 0.420818 0.445548 0.871901 0.041 Uiso 1 1 calc R U . . .
C13 C 0.51116(17) 0.34246(11) 0.81359(16) 0.0452(5) Uani 1 1 d . . . . .
H13 H 0.508294 0.303541 0.865173 0.054 Uiso 1 1 calc R U . . .
C14 C 0.56688(17) 0.31528(11) 0.73466(18) 0.0495(5) Uani 1 1 d . . . . .
H14 H 0.603452 0.258123 0.732462 0.059 Uiso 1 1 calc R U . . .
C15 C 0.56928(17) 0.37125(12) 0.65913(16) 0.0453(5) Uani 1 1 d . . . . .
H15 H 0.606375 0.352119 0.604622 0.054 Uiso 1 1 calc R U . . .
C16 C 0.51755(15) 0.45571(11) 0.66245(13) 0.0339(3) Uani 1 1 d . . . . .
H16 H 0.519477 0.493811 0.610137 0.041 Uiso 1 1 calc R U . . .
C21 C 0.56308(14) 0.80441(10) 0.67999(11) 0.0277(3) Uani 1 1 d . . . . .
H21A H 0.557131 0.779885 0.616193 0.033 Uiso 1 1 calc R U . . .
H21B H 0.651504 0.805871 0.702972 0.033 Uiso 1 1 calc R U . . .
C22 C 0.50570(15) 0.89793(10) 0.68156(11) 0.0299(3) Uani 1 1 d . . . . .
H22A H 0.497965 0.923416 0.618202 0.036 Uiso 1 1 calc R U . . .
H22B H 0.557826 0.937818 0.722224 0.036 Uiso 1 1 calc R U . . .
C23 C 0.37651(15) 0.88582(10) 0.71982(12) 0.0306(3) Uani 1 1 d . . . . .
H23A H 0.374140 0.913251 0.782027 0.037 Uiso 1 1 calc R U . . .
H23B H 0.311488 0.913454 0.677701 0.037 Uiso 1 1 calc R U . . .
C24 C 0.35619(13) 0.78517(9) 0.72562(11) 0.0253(3) Uani 1 1 d . . . . .
H24A H 0.302874 0.770102 0.776675 0.030 Uiso 1 1 calc R U . . .
H24B H 0.317526 0.761767 0.666489 0.030 Uiso 1 1 calc R U . . .
C25 C 0.48656(13) 0.74866(9) 0.74455(9) 0.0215(3) Uani 1 1 d . . . . .
C26 C 0.51882(12) 0.64818(9) 0.73827(10) 0.0208(3) Uani 1 1 d . . . . .
H26 H 0.557945 0.637707 0.678258 0.025 Uiso 1 1 calc R U . . .
C27 C 0.61867(12) 0.64056(9) 0.81634(10) 0.0217(3) Uani 1 1 d . . . . .
C28 C 0.61402(13) 0.71570(9) 0.87169(10) 0.0234(3) Uani 1 1 d . . . . .
C29 C 0.69234(15) 0.72870(10) 0.95010(11) 0.0295(3) Uani 1 1 d . . . . .
H29 H 0.686849 0.780175 0.987525 0.035 Uiso 1 1 calc R U . . .
C30 C 0.77954(15) 0.66287(11) 0.97160(11) 0.0322(3) Uani 1 1 d . . . . .
H30 H 0.835359 0.669739 1.024803 0.039 Uiso 1 1 calc R U . . .
C31 C 0.78719(14) 0.58726(10) 0.91729(12) 0.0307(3) Uani 1 1 d . . . . .
H31 H 0.848061 0.543521 0.933578 0.037 Uiso 1 1 calc R U . . .
C32 C 0.70616(13) 0.57517(9) 0.83908(11) 0.0261(3) Uani 1 1 d . . . . .
H32 H 0.710622 0.523335 0.802084 0.031 Uiso 1 1 calc R U . . .
S1S S 0.10007(3) 0.41863(2) 0.48150(3) 0.03000(12) Uani 1 1 d . . . . .
O1S O 0.01765(12) 0.36406(9) 0.41646(11) 0.0484(4) Uani 1 1 d . . . . .
C1S C 0.17311(19) 0.49744(14) 0.41157(14) 0.0459(4) Uani 1 1 d . . . . .
H1SA H 0.110831 0.539058 0.384934 0.069 Uiso 1 1 calc R U . . .
H1SB H 0.212603 0.466756 0.361367 0.069 Uiso 1 1 calc R U . . .
H1SC H 0.236193 0.529979 0.449826 0.069 Uiso 1 1 calc R U . . .
C2S C 0.23062(19) 0.35074(15) 0.51277(17) 0.0532(5) Uani 1 1 d . . . . .
H2SA H 0.205013 0.301592 0.551606 0.080 Uiso 1 1 calc R U . . .
H2SB H 0.294163 0.386040 0.547483 0.080 Uiso 1 1 calc R U . . .
H2SC H 0.264685 0.327129 0.456464 0.080 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 1.2217(19) . ?
O2 C28 1.3679(17) . ?
O2 C25 1.4709(17) . ?
N1 C1 1.354(2) . ?
N1 C4 1.399(2) . ?
C1 C2 1.555(2) . ?
C2 C3 1.5139(19) . ?
C2 C11 1.5455(18) . ?
C2 C26 1.5630(18) . ?
C3 C8 1.384(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.390(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.402(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.384(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.394(2) . ?
C21 C25 1.5351(19) . ?
C21 C22 1.542(2) . ?
C22 C23 1.543(2) . ?
C23 C24 1.5379(19) . ?
C24 C25 1.5192(19) . ?
C25 C26 1.5599(18) . ?
C26 C27 1.5116(19) . ?
C27 C28 1.390(2) . ?
C27 C32 1.390(2) . ?
C28 C29 1.381(2) . ?
C29 C30 1.390(2) . ?
C30 C31 1.390(2) . ?
C31 C32 1.394(2) . ?
S1S O1S 1.4972(13) . ?
S1S C2S 1.7765(19) . ?
S1S C1S 1.777(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
C28 O2 C25 106.47(10) . . ?
C1 N1 C4 111.42(12) . . ?
O1 C1 N1 126.06(14) . . ?
O1 C1 C2 125.83(13) . . ?
N1 C1 C2 108.11(12) . . ?
C3 C2 C11 113.44(11) . . ?
C3 C2 C1 101.35(11) . . ?
C11 C2 C1 107.16(11) . . ?
C3 C2 C26 115.69(11) . . ?
C11 C2 C26 109.68(11) . . ?
C1 C2 C26 108.79(11) . . ?
C8 C3 C4 119.62(14) . . ?
C8 C3 C2 131.98(14) . . ?
C4 C3 C2 108.40(12) . . ?
C5 C4 C3 122.37(14) . . ?
C5 C4 N1 127.58(14) . . ?
C3 C4 N1 110.02(12) . . ?
C4 C5 C6 117.17(15) . . ?
C7 C6 C5 121.70(15) . . ?
C6 C7 C8 120.39(16) . . ?
C3 C8 C7 118.74(15) . . ?
C12 C11 C16 118.80(14) . . ?
C12 C11 C2 121.95(14) . . ?
C16 C11 C2 119.24(14) . . ?
C11 C12 C13 120.39(18) . . ?
C14 C13 C12 120.12(19) . . ?
C15 C14 C13 119.96(16) . . ?
C14 C15 C16 120.31(19) . . ?
C15 C16 C11 120.41(18) . . ?
C25 C21 C22 105.10(12) . . ?
C21 C22 C23 105.65(11) . . ?
C24 C23 C22 105.77(12) . . ?
C25 C24 C23 103.56(12) . . ?
O2 C25 C24 105.77(11) . . ?
O2 C25 C21 107.06(11) . . ?
C24 C25 C21 102.74(11) . . ?
O2 C25 C26 105.41(10) . . ?
C24 C25 C26 123.35(12) . . ?
C21 C25 C26 111.52(11) . . ?
C27 C26 C25 100.47(11) . . ?
C27 C26 C2 113.53(11) . . ?
C25 C26 C2 117.74(11) . . ?
C28 C27 C32 119.53(13) . . ?
C28 C27 C26 108.38(12) . . ?
C32 C27 C26 132.08(13) . . ?
O2 C28 C29 123.89(13) . . ?
O2 C28 C27 113.19(13) . . ?
C29 C28 C27 122.92(13) . . ?
C28 C29 C30 116.79(14) . . ?
C29 C30 C31 121.70(14) . . ?
C30 C31 C32 120.44(14) . . ?
C27 C32 C31 118.62(14) . . ?
O1S S1S C2S 105.72(9) . . ?
O1S S1S C1S 106.26(9) . . ?
C2S S1S C1S 99.01(11) . . ?

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
C4 N1 C1 O1 -171.45(14) . . . . ?
C4 N1 C1 C2 7.95(15) . . . . ?
O1 C1 C2 C3 171.10(14) . . . . ?
N1 C1 C2 C3 -8.30(14) . . . . ?
O1 C1 C2 C11 -69.78(17) . . . . ?
N1 C1 C2 C11 110.82(13) . . . . ?
O1 C1 C2 C26 48.73(18) . . . . ?
N1 C1 C2 C26 -130.67(12) . . . . ?
C11 C2 C3 C8 71.56(19) . . . . ?
C1 C2 C3 C8 -173.92(14) . . . . ?
C26 C2 C3 C8 -56.5(2) . . . . ?
C11 C2 C3 C4 -108.65(13) . . . . ?
C1 C2 C3 C4 5.87(14) . . . . ?
C26 C2 C3 C4 123.33(13) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -179.80(13) . . . . ?
C8 C3 C4 N1 178.13(12) . . . . ?
C2 C3 C4 N1 -1.69(15) . . . . ?
C1 N1 C4 C5 173.87(14) . . . . ?
C1 N1 C4 C3 -4.12(16) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
N1 C4 C5 C6 -177.56(14) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C4 C3 C8 C7 -0.3(2) . . . . ?
C2 C3 C8 C7 179.47(14) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
C3 C2 C11 C12 -15.60(19) . . . . ?
C1 C2 C11 C12 -126.60(15) . . . . ?
C26 C2 C11 C12 115.47(15) . . . . ?
C3 C2 C11 C16 165.69(13) . . . . ?
C1 C2 C11 C16 54.69(17) . . . . ?
C26 C2 C11 C16 -63.24(17) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C2 C11 C12 C13 -177.59(14) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C2 C11 C16 C15 177.60(15) . . . . ?
C25 C21 C22 C23 -17.62(16) . . . . ?
C21 C22 C23 C24 -7.93(17) . . . . ?
C22 C23 C24 C25 30.74(16) . . . . ?
C28 O2 C25 C24 155.93(11) . . . . ?
C28 O2 C25 C21 -95.02(12) . . . . ?
C28 O2 C25 C26 23.83(13) . . . . ?
C23 C24 C25 O2 70.62(13) . . . . ?
C23 C24 C25 C21 -41.49(14) . . . . ?
C23 C24 C25 C26 -168.29(13) . . . . ?
C22 C21 C25 O2 -74.44(14) . . . . ?
C22 C21 C25 C24 36.72(15) . . . . ?
C22 C21 C25 C26 170.75(12) . . . . ?
O2 C25 C26 C27 -23.24(13) . . . . ?
C24 C25 C26 C27 -144.50(13) . . . . ?
C21 C25 C26 C27 92.59(13) . . . . ?
O2 C25 C26 C2 100.53(13) . . . . ?
C24 C25 C26 C2 -20.73(19) . . . . ?
C21 C25 C26 C2 -143.64(12) . . . . ?
C3 C2 C26 C27 69.45(15) . . . . ?
C11 C2 C26 C27 -60.41(15) . . . . ?
C1 C2 C26 C27 -177.32(11) . . . . ?
C3 C2 C26 C25 -47.49(17) . . . . ?
C11 C2 C26 C25 -177.35(12) . . . . ?
C1 C2 C26 C25 65.74(15) . . . . ?
C25 C26 C27 C28 15.21(14) . . . . ?
C2 C26 C27 C28 -111.43(13) . . . . ?
C25 C26 C27 C32 -165.11(15) . . . . ?
C2 C26 C27 C32 68.25(19) . . . . ?
C25 O2 C28 C29 165.07(13) . . . . ?
C25 O2 C28 C27 -14.73(15) . . . . ?
C32 C27 C28 O2 179.11(12) . . . . ?
C26 C27 C28 O2 -1.15(16) . . . . ?
C32 C27 C28 C29 -0.7(2) . . . . ?
C26 C27 C28 C29 179.05(13) . . . . ?
O2 C28 C29 C30 -178.86(14) . . . . ?
C27 C28 C29 C30 0.9(2) . . . . ?
C28 C29 C30 C31 -0.4(2) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C28 C27 C32 C31 -0.1(2) . . . . ?
C26 C27 C32 C31 -179.73(14) . . . . ?
C30 C31 C32 C27 0.6(2) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_zhk016
_database_code_depnum_ccdc_archive 'CCDC 2235966'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2024-06-05 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         'C33 H34 N2 O4'
_chemical_formula_sum            'C33 H34 N2 O4'
_chemical_formula_weight         522.62

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      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                   18.3540(5)
_cell_length_b                   9.4179(2)
_cell_length_c                   18.5267(5)
_cell_angle_alpha                90
_cell_angle_beta                 119.69
_cell_angle_gamma                90
_cell_volume                     2781.97(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9743
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      68.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    0.654
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7654
_exptl_absorpt_correction_T_max  1.0000
_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            42071
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         68.304
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5100
_reflns_number_gt                4637
_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)+(0.0539P)²+0.7490P] 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       0.00152(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5100
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 -0.05405(6) 0.76686(11) 0.27765(6) 0.0386(2) Uani 1 1 d . . . . .
O2 O 0.39936(5) 0.66552(10) 0.58175(5) 0.0298(2) Uani 1 1 d . . . . .
O3 O 0.35374(6) 0.56160(12) 0.77138(6) 0.0369(2) Uani 1 1 d . . . . .
O4 O 0.45704(5) 0.60276(10) 0.74113(5) 0.0308(2) Uani 1 1 d . . . . .
N1 N 0.08305(6) 0.69811(10) 0.35103(6) 0.0226(2) Uani 1 1 d . . . . .
N2 N 0.32992(6) 0.53951(10) 0.63818(6) 0.0230(2) Uani 1 1 d . . . . .
C1 C 0.00561(7) 0.70236(13) 0.28109(8) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.00198(8) 0.62172(15) 0.20959(8) 0.0329(3) Uani 1 1 d . . . . .
H2A H -0.052110 0.642175 0.158961 0.039 Uiso 1 1 calc R U . . .
H2B H 0.003674 0.518752 0.221076 0.039 Uiso 1 1 calc R U . . .
C3 C 0.07323(10) 0.6578(3) 0.19295(9) 0.0576(5) Uani 1 1 d . . . . .
H3A H 0.054798 0.736964 0.152529 0.069 Uiso 1 1 calc R U . . .
H3B H 0.083432 0.574562 0.166521 0.069 Uiso 1 1 calc R U . . .
C4 C 0.15681(8) 0.69999(14) 0.26975(7) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.15575(7) 0.63822(12) 0.34653(7) 0.0218(2) Uani 1 1 d . . . . .
H5 H 0.149547 0.532704 0.340631 0.026 Uiso 1 1 calc R U . . .
C6 C 0.23214(7) 0.67432(12) 0.43255(7) 0.0214(2) Uani 1 1 d . . . . .
H6 H 0.277365 0.717892 0.424618 0.026 Uiso 1 1 calc R U . . .
C7 C 0.19793(7) 0.78422(12) 0.46742(7) 0.0228(2) Uani 1 1 d . . . . .
C8 C 0.11065(7) 0.78787(12) 0.42052(7) 0.0224(2) Uani 1 1 d . . . . .
C9 C 0.06345(8) 0.87608(13) 0.44184(8) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.003894 0.874258 0.411583 0.033 Uiso 1 1 calc R U . . .
C10 C 0.10656(9) 0.96692(14) 0.50898(8) 0.0323(3) Uani 1 1 d . . . . .
H10 H 0.075763 1.028986 0.524376 0.039 Uiso 1 1 calc R U . . .
C11 C 0.19332(9) 0.96914(14) 0.55396(8) 0.0332(3) Uani 1 1 d . . . . .
H11 H 0.221350 1.034250 0.598572 0.040 Uiso 1 1 calc R U . . .
C12 C 0.23958(8) 0.87609(13) 0.53392(8) 0.0293(3) Uani 1 1 d . . . . .
H12 H 0.299098 0.875637 0.565540 0.035 Uiso 1 1 calc R U . . .
C13 C 0.16580(11) 0.86092(16) 0.27575(11) 0.0468(4) Uani 1 1 d . . . . .
H13A H 0.219239 0.886348 0.324684 0.070 Uiso 1 1 calc R U . . .
H13B H 0.119472 0.902129 0.280752 0.070 Uiso 1 1 calc R U . . .
H13C H 0.164478 0.897858 0.225657 0.070 Uiso 1 1 calc R U . . .
C14 C 0.22885(10) 0.63673(18) 0.26151(9) 0.0431(3) Uani 1 1 d . . . . .
H14A H 0.282407 0.667775 0.308401 0.065 Uiso 1 1 calc R U . . .
H14B H 0.224909 0.668913 0.209386 0.065 Uiso 1 1 calc R U . . .
H14C H 0.225525 0.532875 0.261447 0.065 Uiso 1 1 calc R U . . .
C21 C 0.34228(7) 0.59185(12) 0.57403(7) 0.0222(2) Uani 1 1 d . . . . .
C22 C 0.26784(7) 0.54146(12) 0.49043(7) 0.0220(2) Uani 1 1 d . . . . .
C23 C 0.20980(7) 0.47788(12) 0.51786(7) 0.0232(2) Uani 1 1 d . . . . .
C24 C 0.24946(7) 0.47412(12) 0.60428(7) 0.0229(2) Uani 1 1 d . . . . .
C25 C 0.21330(8) 0.41121(13) 0.64663(8) 0.0294(3) Uani 1 1 d . . . . .
H25 H 0.242681 0.405146 0.705553 0.035 Uiso 1 1 calc R U . . .
C26 C 0.13247(9) 0.35727(14) 0.59980(9) 0.0343(3) Uani 1 1 d . . . . .
H26 H 0.105912 0.314250 0.627127 0.041 Uiso 1 1 calc R U . . .
C27 C 0.09029(8) 0.36547(14) 0.51403(9) 0.0341(3) Uani 1 1 d . . . . .
H27 H 0.034355 0.331338 0.483220 0.041 Uiso 1 1 calc R U . . .
C28 C 0.12903(8) 0.42334(13) 0.47229(8) 0.0294(3) Uani 1 1 d . . . . .
H28 H 0.100514 0.425485 0.413283 0.035 Uiso 1 1 calc R U . . .
C31 C 0.30289(7) 0.43299(13) 0.45285(7) 0.0261(3) Uani 1 1 d . . . . .
C32 C 0.26858(9) 0.29873(15) 0.42824(9) 0.0397(3) Uani 1 1 d . . . . .
H32 H 0.223287 0.269993 0.435954 0.048 Uiso 1 1 calc R U . . .
C33 C 0.30051(12) 0.20566(18) 0.39215(12) 0.0549(4) Uani 1 1 d . . . . .
H33 H 0.276077 0.114283 0.374695 0.066 Uiso 1 1 calc R U . . .
C34 C 0.36679(11) 0.24425(19) 0.38147(10) 0.0509(4) Uani 1 1 d . . . . .
H34 H 0.387995 0.179930 0.356845 0.061 Uiso 1 1 calc R U . . .
C35 C 0.40217(9) 0.37627(18) 0.40659(9) 0.0419(3) Uani 1 1 d . . . . .
H35 H 0.448334 0.403208 0.399855 0.050 Uiso 1 1 calc R U . . .
C36 C 0.37040(8) 0.47057(15) 0.44191(8) 0.0329(3) Uani 1 1 d . . . . .
H36 H 0.395006 0.561947 0.458843 0.040 Uiso 1 1 calc R U . . .
C41 C 0.38033(7) 0.56948(12) 0.72396(7) 0.0250(2) Uani 1 1 d . . . . .
C42 C 0.52003(8) 0.64975(14) 0.82624(7) 0.0314(3) Uani 1 1 d . . . . .
C43 C 0.49092(10) 0.78665(16) 0.84644(10) 0.0455(4) Uani 1 1 d . . . . .
H43A H 0.439903 0.768869 0.849481 0.068 Uiso 1 1 calc R U . . .
H43B H 0.479058 0.856830 0.802918 0.068 Uiso 1 1 calc R U . . .
H43C H 0.534940 0.822992 0.900002 0.068 Uiso 1 1 calc R U . . .
C44 C 0.53547(10) 0.53297(18) 0.88874(9) 0.0475(4) Uani 1 1 d . . . . .
H44A H 0.488103 0.528339 0.899131 0.071 Uiso 1 1 calc R U . . .
H44B H 0.587058 0.553426 0.940870 0.071 Uiso 1 1 calc R U . . .
H44C H 0.541209 0.441774 0.866571 0.071 Uiso 1 1 calc R U . . .
C45 C 0.59643(9) 0.67356(19) 0.81664(10) 0.0452(4) Uani 1 1 d . . . . .
H45A H 0.583752 0.745969 0.774031 0.068 Uiso 1 1 calc R U . . .
H45B H 0.611567 0.584510 0.800005 0.068 Uiso 1 1 calc R U . . .
H45C H 0.643388 0.705606 0.869676 0.068 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 1.2260(16) . ?
O2 C21 1.2046(15) . ?
O3 C41 1.2001(16) . ?
O4 C41 1.3184(15) . ?
O4 C42 1.4876(14) . ?
N1 C1 1.3698(15) . ?
N1 C8 1.4080(15) . ?
N1 C5 1.4886(14) . ?
N2 C21 1.4049(15) . ?
N2 C41 1.4159(15) . ?
N2 C24 1.4269(14) . ?
C1 C2 1.4995(18) . ?
C2 C3 1.523(2) . ?
C3 C4 1.5407(18) . ?
C4 C13 1.523(2) . ?
C4 C14 1.5253(18) . ?
C4 C5 1.5458(15) . ?
C5 C6 1.5516(14) . ?
C6 C7 1.5115(15) . ?
C6 C22 1.5649(15) . ?
C7 C12 1.3849(17) . ?
C7 C8 1.3941(16) . ?
C8 C9 1.3912(17) . ?
C9 C10 1.3892(19) . ?
C10 C11 1.384(2) . ?
C11 C12 1.3925(18) . ?
C21 C22 1.5474(14) . ?
C22 C23 1.5126(15) . ?
C22 C31 1.5447(15) . ?
C23 C28 1.3908(16) . ?
C23 C24 1.3929(16) . ?
C24 C25 1.3867(17) . ?
C25 C26 1.3917(19) . ?
C26 C27 1.383(2) . ?
C27 C28 1.3949(19) . ?
C31 C32 1.3851(19) . ?
C31 C36 1.3967(18) . ?
C32 C33 1.395(2) . ?
C33 C34 1.375(3) . ?
C34 C35 1.373(3) . ?
C35 C36 1.3909(19) . ?
C42 C43 1.512(2) . ?
C42 C45 1.515(2) . ?
C42 C44 1.518(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
C41 O4 C42 120.18(9) . . ?
C1 N1 C8 125.61(10) . . ?
C1 N1 C5 119.80(9) . . ?
C8 N1 C5 110.62(9) . . ?
C21 N2 C41 126.16(9) . . ?
C21 N2 C24 110.17(9) . . ?
C41 N2 C24 122.57(10) . . ?
O1 C1 N1 123.03(12) . . ?
O1 C1 C2 123.88(11) . . ?
N1 C1 C2 113.09(10) . . ?
C1 C2 C3 113.52(12) . . ?
C2 C3 C4 115.62(11) . . ?
C13 C4 C14 109.15(12) . . ?
C13 C4 C3 110.27(14) . . ?
C14 C4 C3 108.83(12) . . ?
C13 C4 C5 110.97(11) . . ?
C14 C4 C5 110.60(10) . . ?
C3 C4 C5 106.99(10) . . ?
N1 C5 C4 109.22(9) . . ?
N1 C5 C6 103.79(8) . . ?
C4 C5 C6 116.47(9) . . ?
C7 C6 C5 103.52(9) . . ?
C7 C6 C22 112.10(9) . . ?
C5 C6 C22 112.78(9) . . ?
C12 C7 C8 119.77(11) . . ?
C12 C7 C6 130.17(10) . . ?
C8 C7 C6 110.05(10) . . ?
C9 C8 C7 121.51(11) . . ?
C9 C8 N1 128.72(11) . . ?
C7 C8 N1 109.69(10) . . ?
C10 C9 C8 117.60(11) . . ?
C11 C10 C9 121.57(11) . . ?
C10 C11 C12 120.10(12) . . ?
C7 C12 C11 119.32(12) . . ?
O2 C21 N2 126.65(10) . . ?
O2 C21 C22 125.48(10) . . ?
N2 C21 C22 107.85(9) . . ?
C23 C22 C31 114.18(9) . . ?
C23 C22 C21 101.82(9) . . ?
C31 C22 C21 107.19(9) . . ?
C23 C22 C6 114.91(9) . . ?
C31 C22 C6 110.27(9) . . ?
C21 C22 C6 107.64(9) . . ?
C28 C23 C24 118.78(11) . . ?
C28 C23 C22 131.19(11) . . ?
C24 C23 C22 110.01(9) . . ?
C25 C24 C23 122.49(11) . . ?
C25 C24 N2 128.06(11) . . ?
C23 C24 N2 109.43(10) . . ?
C24 C25 C26 117.67(12) . . ?
C27 C26 C25 120.88(12) . . ?
C26 C27 C28 120.67(11) . . ?
C23 C28 C27 119.37(12) . . ?
C32 C31 C36 118.36(12) . . ?
C32 C31 C22 121.94(12) . . ?
C36 C31 C22 119.69(11) . . ?
C31 C32 C33 120.05(15) . . ?
C34 C33 C32 120.96(15) . . ?
C35 C34 C33 119.63(14) . . ?
C34 C35 C36 119.97(15) . . ?
C35 C36 C31 121.01(13) . . ?
O3 C41 O4 127.67(11) . . ?
O3 C41 N2 122.19(11) . . ?
O4 C41 N2 110.13(10) . . ?
O4 C42 C43 109.37(10) . . ?
O4 C42 C45 101.42(10) . . ?
C43 C42 C45 111.34(12) . . ?
O4 C42 C44 110.27(11) . . ?
C43 C42 C44 112.60(13) . . ?
C45 C42 C44 111.27(12) . . ?

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
C8 N1 C1 O1 -14.53(19) . . . . ?
C5 N1 C1 O1 -169.93(11) . . . . ?
C8 N1 C1 C2 164.84(11) . . . . ?
C5 N1 C1 C2 9.44(15) . . . . ?
O1 C1 C2 C3 130.15(15) . . . . ?
N1 C1 C2 C3 -49.22(16) . . . . ?
C1 C2 C3 C4 31.2(2) . . . . ?
C2 C3 C4 C13 -98.87(18) . . . . ?
C2 C3 C4 C14 141.44(16) . . . . ?
C2 C3 C4 C5 21.9(2) . . . . ?
C1 N1 C5 C4 46.42(13) . . . . ?
C8 N1 C5 C4 -112.39(10) . . . . ?
C1 N1 C5 C6 171.29(10) . . . . ?
C8 N1 C5 C6 12.48(11) . . . . ?
C13 C4 C5 N1 60.72(13) . . . . ?
C14 C4 C5 N1 -178.00(10) . . . . ?
C3 C4 C5 N1 -59.61(14) . . . . ?
C13 C4 C5 C6 -56.39(14) . . . . ?
C14 C4 C5 C6 64.89(14) . . . . ?
C3 C4 C5 C6 -176.72(12) . . . . ?
N1 C5 C6 C7 -14.83(11) . . . . ?
C4 C5 C6 C7 105.23(11) . . . . ?
N1 C5 C6 C22 106.55(10) . . . . ?
C4 C5 C6 C22 -133.39(10) . . . . ?
C5 C6 C7 C12 -165.59(12) . . . . ?
C22 C6 C7 C12 72.58(15) . . . . ?
C5 C6 C7 C8 13.09(12) . . . . ?
C22 C6 C7 C8 -108.74(10) . . . . ?
C12 C7 C8 C9 -3.96(17) . . . . ?
C6 C7 C8 C9 177.20(10) . . . . ?
C12 C7 C8 N1 173.06(10) . . . . ?
C6 C7 C8 N1 -5.78(13) . . . . ?
C1 N1 C8 C9 14.83(19) . . . . ?
C5 N1 C8 C9 172.13(11) . . . . ?
C1 N1 C8 C7 -161.92(11) . . . . ?
C5 N1 C8 C7 -4.62(12) . . . . ?
C7 C8 C9 C10 3.65(17) . . . . ?
N1 C8 C9 C10 -172.76(11) . . . . ?
C8 C9 C10 C11 -0.72(19) . . . . ?
C9 C10 C11 C12 -1.9(2) . . . . ?
C8 C7 C12 C11 1.25(18) . . . . ?
C6 C7 C12 C11 179.82(12) . . . . ?
C10 C11 C12 C7 1.6(2) . . . . ?
C41 N2 C21 O2 3.31(18) . . . . ?
C24 N2 C21 O2 171.49(11) . . . . ?
C41 N2 C21 C22 -175.18(10) . . . . ?
C24 N2 C21 C22 -7.00(12) . . . . ?
O2 C21 C22 C23 -170.05(11) . . . . ?
N2 C21 C22 C23 8.46(11) . . . . ?
O2 C21 C22 C31 69.77(14) . . . . ?
N2 C21 C22 C31 -111.71(10) . . . . ?
O2 C21 C22 C6 -48.85(14) . . . . ?
N2 C21 C22 C6 129.67(9) . . . . ?
C7 C6 C22 C23 49.86(12) . . . . ?
C5 C6 C22 C23 -66.52(12) . . . . ?
C7 C6 C22 C31 -179.38(9) . . . . ?
C5 C6 C22 C31 64.24(11) . . . . ?
C7 C6 C22 C21 -62.76(11) . . . . ?
C5 C6 C22 C21 -179.14(9) . . . . ?
C31 C22 C23 C28 -70.35(16) . . . . ?
C21 C22 C23 C28 174.50(12) . . . . ?
C6 C22 C23 C28 58.49(16) . . . . ?
C31 C22 C23 C24 107.93(11) . . . . ?
C21 C22 C23 C24 -7.21(12) . . . . ?
C6 C22 C23 C24 -123.22(10) . . . . ?
C28 C23 C24 C25 3.56(17) . . . . ?
C22 C23 C24 C25 -174.97(11) . . . . ?
C28 C23 C24 N2 -177.99(10) . . . . ?
C22 C23 C24 N2 3.48(13) . . . . ?
C21 N2 C24 C25 -179.31(11) . . . . ?
C41 N2 C24 C25 -10.62(18) . . . . ?
C21 N2 C24 C23 2.35(12) . . . . ?
C41 N2 C24 C23 171.03(10) . . . . ?
C23 C24 C25 C26 -3.51(18) . . . . ?
N2 C24 C25 C26 178.34(11) . . . . ?
C24 C25 C26 C27 0.5(2) . . . . ?
C25 C26 C27 C28 2.4(2) . . . . ?
C24 C23 C28 C27 -0.55(18) . . . . ?
C22 C23 C28 C27 177.61(12) . . . . ?
C26 C27 C28 C23 -2.4(2) . . . . ?
C23 C22 C31 C32 14.80(16) . . . . ?
C21 C22 C31 C32 126.75(12) . . . . ?
C6 C22 C31 C32 -116.35(13) . . . . ?
C23 C22 C31 C36 -166.12(10) . . . . ?
C21 C22 C31 C36 -54.16(14) . . . . ?
C6 C22 C31 C36 62.74(13) . . . . ?
C36 C31 C32 C33 -1.1(2) . . . . ?
C22 C31 C32 C33 177.96(13) . . . . ?
C31 C32 C33 C34 0.9(3) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 -0.6(2) . . . . ?
C34 C35 C36 C31 0.4(2) . . . . ?
C32 C31 C36 C35 0.51(19) . . . . ?
C22 C31 C36 C35 -178.61(11) . . . . ?
C42 O4 C41 O3 -6.0(2) . . . . ?
C42 O4 C41 N2 175.17(10) . . . . ?
C21 N2 C41 O3 155.38(12) . . . . ?
C24 N2 C41 O3 -11.43(18) . . . . ?
C21 N2 C41 O4 -25.72(15) . . . . ?
C24 N2 C41 O4 167.47(10) . . . . ?
C41 O4 C42 C43 -62.99(15) . . . . ?
C41 O4 C42 C45 179.33(12) . . . . ?
C41 O4 C42 C44 61.35(16) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_zhk015
_database_code_depnum_ccdc_archive 'CCDC 2235965'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2024-06-05 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         'C33 H34 N2 O4'
_chemical_formula_sum            'C33 H34 N2 O4'
_chemical_formula_weight         522.62

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.5642(3)
_cell_length_b                   14.7819(2)
_cell_length_c                   10.4569(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2714.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      79.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.333
_exptl_absorpt_coefficient_mu    0.671
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7443
_exptl_absorpt_correction_T_max  0.9631
_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            15781
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.908
_diffrn_reflns_theta_max         79.526
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_point_group_measured_fraction_full 0.774
_reflns_number_total             4474
_reflns_number_gt                4340
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.465
_reflns_Friedel_fraction_max     0.510
_reflns_Friedel_fraction_full    0.528

_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)+(0.0493P)²+0.4765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4474
_refine_ls_number_parameters     357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.17855(9) 0.46650(12) 0.4874(2) 0.0438(4) Uani 1 1 d . . . . .
O2 O 0.46918(9) 0.79380(9) 0.31234(15) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.36394(9) 0.97646(9) 0.56091(16) 0.0306(3) Uani 1 1 d . . . . .
O4 O 0.42757(8) 0.95753(9) 0.37498(16) 0.0292(3) Uani 1 1 d . . . . .
N1 N 0.28537(9) 0.55078(10) 0.45313(17) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.41087(8) 0.83772(10) 0.50423(16) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.20816(12) 0.53707(15) 0.4506(2) 0.0311(4) Uani 1 1 d . . . . .
C2 C 0.16515(11) 0.61653(15) 0.3981(3) 0.0358(5) Uani 1 1 d . . . . .
H2A H 0.167540 0.666909 0.460339 0.043 Uiso 1 1 calc R U . . .
H2B H 0.111009 0.599553 0.387319 0.043 Uiso 1 1 calc R U . . .
C3 C 0.19675(12) 0.64904(16) 0.2692(2) 0.0343(5) Uani 1 1 d . . . . .
H3A H 0.182653 0.713367 0.257552 0.041 Uiso 1 1 calc R U . . .
H3B H 0.171844 0.614098 0.200061 0.041 Uiso 1 1 calc R U . . .
C4 C 0.28462(11) 0.63997(13) 0.2539(2) 0.0263(4) Uani 1 1 d . . . . .
C5 C 0.31943(10) 0.63057(11) 0.38863(19) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.307103 0.686066 0.439259 0.025 Uiso 1 1 calc R U . . .
C6 C 0.40728(9) 0.61304(11) 0.39568(19) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.429108 0.615869 0.307443 0.024 Uiso 1 1 calc R U . . .
C7 C 0.41273(11) 0.51642(12) 0.44491(19) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.34076(11) 0.48499(12) 0.4792(2) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.33013(12) 0.39867(14) 0.5296(2) 0.0315(4) Uani 1 1 d . . . . .
H9 H 0.281019 0.378036 0.554060 0.038 Uiso 1 1 calc R U . . .
C10 C 0.39418(14) 0.34357(14) 0.5428(2) 0.0361(5) Uani 1 1 d . . . . .
H10 H 0.388515 0.284427 0.577079 0.043 Uiso 1 1 calc R U . . .
C11 C 0.46562(13) 0.37330(14) 0.5072(3) 0.0353(5) Uani 1 1 d . . . . .
H11 H 0.508337 0.334455 0.516573 0.042 Uiso 1 1 calc R U . . .
C12 C 0.47541(11) 0.46021(13) 0.4573(2) 0.0288(4) Uani 1 1 d . . . . .
H12A H 0.524491 0.480527 0.432103 0.035 Uiso 1 1 calc R U . . .
C13 C 0.30283(12) 0.55601(16) 0.1739(2) 0.0340(5) Uani 1 1 d . . . . .
H13A H 0.358080 0.550837 0.163041 0.051 Uiso 1 1 calc R U . . .
H13B H 0.278573 0.561408 0.089802 0.051 Uiso 1 1 calc R U . . .
H13C H 0.283495 0.502025 0.217500 0.051 Uiso 1 1 calc R U . . .
C14 C 0.31511(14) 0.72421(16) 0.1865(2) 0.0367(5) Uani 1 1 d . . . . .
H14A H 0.369570 0.716582 0.169197 0.055 Uiso 1 1 calc R U . . .
H14B H 0.307469 0.777191 0.241309 0.055 Uiso 1 1 calc R U . . .
H14C H 0.287837 0.732891 0.105616 0.055 Uiso 1 1 calc R U . . .
C21 C 0.44536(10) 0.77715(12) 0.41729(19) 0.0209(3) Uani 1 1 d . . . . .
C22 C 0.44928(9) 0.68328(11) 0.48256(18) 0.0198(3) Uani 1 1 d . . . . .
C23 C 0.40985(9) 0.70009(12) 0.60805(19) 0.0203(3) Uani 1 1 d . . . . .
C24 C 0.38941(9) 0.79146(12) 0.61824(19) 0.0205(3) Uani 1 1 d . . . . .
C25 C 0.35473(11) 0.82503(14) 0.7272(2) 0.0266(4) Uani 1 1 d . . . . .
H25 H 0.341779 0.887228 0.734167 0.032 Uiso 1 1 calc R U . . .
C26 C 0.35788(12) 0.67329(15) 0.8161(2) 0.0303(4) Uani 1 1 d . . . . .
H26 H 0.345874 0.633057 0.884055 0.036 Uiso 1 1 calc R U . . .
C27 C 0.33937(12) 0.76458(16) 0.8264(2) 0.0324(4) Uani 1 1 d . . . . .
H27 H 0.315849 0.786127 0.902331 0.039 Uiso 1 1 calc R U . . .
C28 C 0.39385(11) 0.64067(13) 0.7070(2) 0.0263(4) Uani 1 1 d . . . . .
H28 H 0.407263 0.578584 0.700378 0.032 Uiso 1 1 calc R U . . .
C31 C 0.53493(10) 0.66413(11) 0.4967(2) 0.0226(4) Uani 1 1 d . . . . .
C32 C 0.57807(11) 0.64139(13) 0.3892(2) 0.0290(4) Uani 1 1 d . . . . .
H32 H 0.554006 0.635140 0.308347 0.035 Uiso 1 1 calc R U . . .
C33 C 0.65604(12) 0.62788(14) 0.4003(3) 0.0339(5) Uani 1 1 d . . . . .
H33 H 0.684763 0.610157 0.327459 0.041 Uiso 1 1 calc R U . . .
C34 C 0.69214(12) 0.64005(15) 0.5165(3) 0.0380(5) Uani 1 1 d . . . . .
H34 H 0.745554 0.631163 0.523361 0.046 Uiso 1 1 calc R U . . .
C35 C 0.65047(12) 0.66511(15) 0.6225(3) 0.0360(5) Uani 1 1 d . . . . .
H35 H 0.675464 0.674976 0.701880 0.043 Uiso 1 1 calc R U . . .
C36 C 0.57160(11) 0.67607(13) 0.6137(2) 0.0280(4) Uani 1 1 d . . . . .
H36 H 0.542955 0.691670 0.687499 0.034 Uiso 1 1 calc R U . . .
C41 C 0.39813(9) 0.93157(12) 0.4843(2) 0.0215(3) Uani 1 1 d . . . . .
C42 C 0.42138(12) 1.05343(13) 0.3325(2) 0.0318(5) Uani 1 1 d . . . . .
C43 C 0.33845(16) 1.0801(2) 0.3206(4) 0.0550(8) Uani 1 1 d . . . . .
H43A H 0.311089 1.033939 0.271515 0.082 Uiso 1 1 calc R U . . .
H43B H 0.334653 1.138458 0.276548 0.082 Uiso 1 1 calc R U . . .
H43C H 0.315933 1.085225 0.406049 0.082 Uiso 1 1 calc R U . . .
C44 C 0.45858(14) 1.04948(16) 0.2023(3) 0.0392(5) Uani 1 1 d . . . . .
H44A H 0.431262 1.006139 0.148254 0.059 Uiso 1 1 calc R U . . .
H44B H 0.511684 1.030210 0.211630 0.059 Uiso 1 1 calc R U . . .
H44C H 0.456933 1.109514 0.162675 0.059 Uiso 1 1 calc R U . . .
C45 C 0.46662(18) 1.11222(16) 0.4247(3) 0.0484(6) Uani 1 1 d . . . . .
H45A H 0.442316 1.111102 0.509080 0.073 Uiso 1 1 calc R U . . .
H45B H 0.467987 1.174520 0.392780 0.073 Uiso 1 1 calc R U . . .
H45C H 0.518675 1.088879 0.431723 0.073 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 1.227(3) . ?
O2 C21 1.200(3) . ?
O3 C41 1.201(3) . ?
O4 C41 1.312(2) . ?
O4 C42 1.490(2) . ?
N1 C1 1.372(3) . ?
N1 C8 1.402(3) . ?
N1 C5 1.485(2) . ?
N2 C21 1.412(2) . ?
N2 C41 1.421(2) . ?
N2 C24 1.425(2) . ?
C1 C2 1.501(3) . ?
C2 C3 1.535(4) . ?
C3 C4 1.557(3) . ?
C4 C14 1.528(3) . ?
C4 C13 1.530(3) . ?
C4 C5 1.543(3) . ?
C5 C6 1.566(2) . ?
C6 C7 1.521(2) . ?
C6 C22 1.564(2) . ?
C7 C12 1.385(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.396(3) . ?
C10 C11 1.381(4) . ?
C11 C12 1.397(3) . ?
C21 C22 1.548(2) . ?
C22 C23 1.504(3) . ?
C22 C31 1.538(2) . ?
C23 C28 1.386(3) . ?
C23 C24 1.402(2) . ?
C24 C25 1.384(3) . ?
C25 C27 1.396(3) . ?
C26 C28 1.391(3) . ?
C26 C27 1.392(3) . ?
C31 C36 1.394(3) . ?
C31 C32 1.396(3) . ?
C32 C33 1.389(3) . ?
C33 C34 1.383(4) . ?
C34 C35 1.379(4) . ?
C35 C36 1.398(3) . ?
C42 C44 1.511(3) . ?
C42 C43 1.514(3) . ?
C42 C45 1.522(4) . ?

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
C41 O4 C42 120.62(15) . . ?
C1 N1 C8 125.95(16) . . ?
C1 N1 C5 120.48(16) . . ?
C8 N1 C5 111.10(15) . . ?
C21 N2 C41 126.30(16) . . ?
C21 N2 C24 110.35(14) . . ?
C41 N2 C24 123.35(16) . . ?
O1 C1 N1 122.6(2) . . ?
O1 C1 C2 124.51(19) . . ?
N1 C1 C2 112.89(18) . . ?
C1 C2 C3 112.62(18) . . ?
C2 C3 C4 114.93(18) . . ?
C14 C4 C13 109.60(19) . . ?
C14 C4 C5 110.85(16) . . ?
C13 C4 C5 110.09(16) . . ?
C14 C4 C3 108.94(18) . . ?
C13 C4 C3 109.46(17) . . ?
C5 C4 C3 107.86(17) . . ?
N1 C5 C4 109.08(15) . . ?
N1 C5 C6 104.13(14) . . ?
C4 C5 C6 116.64(16) . . ?
C7 C6 C22 113.39(15) . . ?
C7 C6 C5 103.48(13) . . ?
C22 C6 C5 112.46(14) . . ?
C12 C7 C8 119.79(17) . . ?
C12 C7 C6 130.14(17) . . ?
C8 C7 C6 110.07(15) . . ?
C9 C8 C7 121.63(18) . . ?
C9 C8 N1 128.01(18) . . ?
C7 C8 N1 110.35(16) . . ?
C8 C9 C10 117.64(19) . . ?
C11 C10 C9 121.32(19) . . ?
C10 C11 C12 120.4(2) . . ?
C7 C12 C11 119.24(19) . . ?
O2 C21 N2 127.46(17) . . ?
O2 C21 C22 124.86(17) . . ?
N2 C21 C22 107.67(15) . . ?
C23 C22 C31 113.38(15) . . ?
C23 C22 C21 102.48(14) . . ?
C31 C22 C21 104.53(13) . . ?
C23 C22 C6 113.52(14) . . ?
C31 C22 C6 113.26(14) . . ?
C21 C22 C6 108.53(15) . . ?
C28 C23 C24 120.13(18) . . ?
C28 C23 C22 129.78(17) . . ?
C24 C23 C22 110.08(16) . . ?
C25 C24 C23 121.39(18) . . ?
C25 C24 N2 129.27(17) . . ?
C23 C24 N2 109.33(16) . . ?
C24 C25 C27 117.88(19) . . ?
C28 C26 C27 120.36(19) . . ?
C26 C27 C25 121.2(2) . . ?
C23 C28 C26 119.01(19) . . ?
C36 C31 C32 119.08(17) . . ?
C36 C31 C22 120.88(18) . . ?
C32 C31 C22 119.85(18) . . ?
C33 C32 C31 120.2(2) . . ?
C34 C33 C32 120.4(2) . . ?
C35 C34 C33 119.89(18) . . ?
C34 C35 C36 120.3(2) . . ?
C31 C36 C35 120.1(2) . . ?
O3 C41 O4 128.08(17) . . ?
O3 C41 N2 121.34(18) . . ?
O4 C41 N2 110.58(16) . . ?
O4 C42 C44 101.55(16) . . ?
O4 C42 C43 110.04(18) . . ?
C44 C42 C43 110.6(2) . . ?
O4 C42 C45 108.44(19) . . ?
C44 C42 C45 111.5(2) . . ?
C43 C42 C45 113.9(2) . . ?

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
C8 N1 C1 O1 9.5(4) . . . . ?
C5 N1 C1 O1 170.0(2) . . . . ?
C8 N1 C1 C2 -170.2(2) . . . . ?
C5 N1 C1 C2 -9.7(3) . . . . ?
O1 C1 C2 C3 -128.8(2) . . . . ?
N1 C1 C2 C3 50.9(3) . . . . ?
C1 C2 C3 C4 -34.4(3) . . . . ?
C2 C3 C4 C14 -139.3(2) . . . . ?
C2 C3 C4 C13 100.9(2) . . . . ?
C2 C3 C4 C5 -18.9(2) . . . . ?
C1 N1 C5 C4 -46.4(2) . . . . ?
C8 N1 C5 C4 116.81(17) . . . . ?
C1 N1 C5 C6 -171.57(18) . . . . ?
C8 N1 C5 C6 -8.4(2) . . . . ?
C14 C4 C5 N1 177.10(16) . . . . ?
C13 C4 C5 N1 -61.5(2) . . . . ?
C3 C4 C5 N1 57.91(19) . . . . ?
C14 C4 C5 C6 -65.4(2) . . . . ?
C13 C4 C5 C6 56.1(2) . . . . ?
C3 C4 C5 C6 175.46(15) . . . . ?
N1 C5 C6 C7 9.04(18) . . . . ?
C4 C5 C6 C7 -111.18(17) . . . . ?
N1 C5 C6 C22 -113.69(16) . . . . ?
C4 C5 C6 C22 126.08(17) . . . . ?
C22 C6 C7 C12 -65.9(3) . . . . ?
C5 C6 C7 C12 172.0(2) . . . . ?
C22 C6 C7 C8 114.90(17) . . . . ?
C5 C6 C7 C8 -7.2(2) . . . . ?
C12 C7 C8 C9 1.9(3) . . . . ?
C6 C7 C8 C9 -178.82(19) . . . . ?
C12 C7 C8 N1 -177.01(19) . . . . ?
C6 C7 C8 N1 2.3(2) . . . . ?
C1 N1 C8 C9 -12.6(4) . . . . ?
C5 N1 C8 C9 -174.7(2) . . . . ?
C1 N1 C8 C7 166.2(2) . . . . ?
C5 N1 C8 C7 4.1(2) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
N1 C8 C9 C10 177.7(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C8 C7 C12 C11 -1.6(3) . . . . ?
C6 C7 C12 C11 179.3(2) . . . . ?
C10 C11 C12 C7 0.5(4) . . . . ?
C41 N2 C21 O2 -0.6(3) . . . . ?
C24 N2 C21 O2 179.21(18) . . . . ?
C41 N2 C21 C22 178.10(15) . . . . ?
C24 N2 C21 C22 -2.11(18) . . . . ?
O2 C21 C22 C23 -178.35(18) . . . . ?
N2 C21 C22 C23 2.93(17) . . . . ?
O2 C21 C22 C31 63.1(2) . . . . ?
N2 C21 C22 C31 -115.57(15) . . . . ?
O2 C21 C22 C6 -58.0(2) . . . . ?
N2 C21 C22 C6 123.28(15) . . . . ?
C7 C6 C22 C23 -71.32(18) . . . . ?
C5 C6 C22 C23 45.7(2) . . . . ?
C7 C6 C22 C31 59.8(2) . . . . ?
C5 C6 C22 C31 176.82(15) . . . . ?
C7 C6 C22 C21 175.45(14) . . . . ?
C5 C6 C22 C21 -67.57(18) . . . . ?
C31 C22 C23 C28 -69.8(2) . . . . ?
C21 C22 C23 C28 178.17(18) . . . . ?
C6 C22 C23 C28 61.3(2) . . . . ?
C31 C22 C23 C24 109.26(16) . . . . ?
C21 C22 C23 C24 -2.81(18) . . . . ?
C6 C22 C23 C24 -119.64(16) . . . . ?
C28 C23 C24 C25 1.5(3) . . . . ?
C22 C23 C24 C25 -177.62(15) . . . . ?
C28 C23 C24 N2 -179.17(16) . . . . ?
C22 C23 C24 N2 1.71(19) . . . . ?
C21 N2 C24 C25 179.57(18) . . . . ?
C41 N2 C24 C25 -0.6(3) . . . . ?
C21 N2 C24 C23 0.31(19) . . . . ?
C41 N2 C24 C23 -179.90(15) . . . . ?
C23 C24 C25 C27 -1.1(3) . . . . ?
N2 C24 C25 C27 179.73(18) . . . . ?
C28 C26 C27 C25 1.4(3) . . . . ?
C24 C25 C27 C26 -0.4(3) . . . . ?
C24 C23 C28 C26 -0.4(3) . . . . ?
C22 C23 C28 C26 178.50(18) . . . . ?
C27 C26 C28 C23 -1.0(3) . . . . ?
C23 C22 C31 C36 -9.3(2) . . . . ?
C21 C22 C31 C36 101.48(19) . . . . ?
C6 C22 C31 C36 -140.56(17) . . . . ?
C23 C22 C31 C32 175.78(16) . . . . ?
C21 C22 C31 C32 -73.41(19) . . . . ?
C6 C22 C31 C32 44.6(2) . . . . ?
C36 C31 C32 C33 2.2(3) . . . . ?
C22 C31 C32 C33 177.18(17) . . . . ?
C31 C32 C33 C34 -2.4(3) . . . . ?
C32 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 1.6(3) . . . . ?
C32 C31 C36 C35 -0.1(3) . . . . ?
C22 C31 C36 C35 -175.05(18) . . . . ?
C34 C35 C36 C31 -1.8(3) . . . . ?
C42 O4 C41 O3 0.5(3) . . . . ?
C42 O4 C41 N2 179.88(16) . . . . ?
C21 N2 C41 O3 175.24(17) . . . . ?
C24 N2 C41 O3 -4.5(3) . . . . ?
C21 N2 C41 O4 -4.2(2) . . . . ?
C24 N2 C41 O4 176.09(15) . . . . ?
C41 O4 C42 C44 -177.05(18) . . . . ?
C41 O4 C42 C43 -59.9(3) . . . . ?
C41 O4 C42 C45 65.4(2) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
