# 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_SQ231206_1_a
_database_code_depnum_ccdc_archive 'CCDC 2313260'
loop_
_audit_author_name
_audit_author_address
'Qiang Sha'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N O6'
_chemical_formula_sum            'C23 H23 N O6'
_chemical_formula_weight         409.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.4110(15)
_cell_length_b                   9.4820(13)
_cell_length_c                   36.247(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.857(3)
_cell_angle_gamma                90
_cell_volume                     4263.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9737
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      21.93

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            40423
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.220
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7486
_reflns_number_gt                4491
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (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)+(0.0458P)²+6.8187P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7486
_refine_ls_number_parameters     573
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.076
_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
C1 C 0.0725(3) 0.7626(4) 0.50023(10) 0.0377(9) Uani 1 1 d . . . . .
C2 C -0.0334(3) 0.7257(4) 0.49734(10) 0.0399(10) Uani 1 1 d . . . . .
C3 C -0.0805(3) 0.7538(4) 0.53222(11) 0.0431(10) Uani 1 1 d . . . . .
C4 C 0.0004(3) 0.8066(4) 0.55522(11) 0.0432(10) Uani 1 1 d . . . . .
C5 C 0.1589(3) 0.7538(4) 0.47312(10) 0.0413(10) Uani 1 1 d . . . . .
C6 C 0.2209(4) 0.8696(5) 0.46562(12) 0.0606(13) Uani 1 1 d . . . . .
H6 H 0.208764 0.954129 0.477807 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3014(4) 0.8617(7) 0.44005(13) 0.0773(16) Uani 1 1 d . . . . .
H7 H 0.343567 0.940376 0.435327 0.093 Uiso 1 1 calc R U . . .
C8 C 0.3184(4) 0.7387(7) 0.42192(13) 0.0763(16) Uani 1 1 d . . . . .
H8 H 0.372919 0.733152 0.404962 0.092 Uiso 1 1 calc R U . . .
C9 C 0.2561(4) 0.6230(6) 0.42840(13) 0.0704(14) Uani 1 1 d . . . . .
H9 H 0.267011 0.539841 0.415445 0.084 Uiso 1 1 calc R U . . .
C10 C 0.1766(4) 0.6300(5) 0.45431(12) 0.0576(12) Uani 1 1 d . . . . .
H10 H 0.134972 0.550831 0.459026 0.069 Uiso 1 1 calc R U . . .
C11 C -0.0863(4) 0.6574(5) 0.46513(12) 0.0494(11) Uani 1 1 d . . . . .
C12 C -0.1004(6) 0.6557(6) 0.40030(13) 0.0935(17) Uani 1 1 d . U . . .
H12A H -0.177684 0.641408 0.400825 0.112 Uiso 0.71(4) 1 calc R U P A 1
H12B H -0.065858 0.564775 0.397378 0.112 Uiso 0.71(4) 1 calc R U P A 1
H12C H -0.042265 0.598328 0.391166 0.112 Uiso 0.29(4) 1 calc R U P A 2
H12D H -0.158129 0.592027 0.406570 0.112 Uiso 0.29(4) 1 calc R U P A 2
C13A C -0.074(2) 0.7491(18) 0.3700(3) 0.111(4) Uani 0.71(4) 1 d . U P A 1
H13A H -0.101917 0.841606 0.374624 0.167 Uiso 0.71(4) 1 calc R U P A 1
H13B H -0.105299 0.713164 0.347379 0.167 Uiso 0.71(4) 1 calc R U P A 1
H13C H 0.002981 0.754158 0.368136 0.167 Uiso 0.71(4) 1 calc R U P A 1
C13B C -0.135(4) 0.733(4) 0.3740(10) 0.104(7) Uani 0.29(4) 1 d . U P A 2
H13D H -0.165968 0.817477 0.383766 0.156 Uiso 0.29(4) 1 calc R U P A 2
H13E H -0.188388 0.683144 0.359501 0.156 Uiso 0.29(4) 1 calc R U P A 2
H13F H -0.075951 0.758212 0.358666 0.156 Uiso 0.29(4) 1 calc R U P A 2
C14 C -0.1924(4) 0.7450(4) 0.54357(13) 0.0484(11) Uani 1 1 d . . . . .
C15 C -0.3748(4) 0.7260(8) 0.52332(17) 0.0973(18) Uani 1 1 d . U . . .
H15A H -0.386584 0.630042 0.531506 0.117 Uiso 0.43(3) 1 calc R U P B 1
H15B H -0.392008 0.788560 0.543476 0.117 Uiso 0.43(3) 1 calc R U P B 1
H15C H -0.408355 0.817183 0.526913 0.117 Uiso 0.57(3) 1 calc R U P B 2
H15D H -0.382428 0.670290 0.545521 0.117 Uiso 0.57(3) 1 calc R U P B 2
C16A C -0.4429(15) 0.754(4) 0.4940(6) 0.112(6) Uani 0.43(3) 1 d . U P B 1
H16A H -0.440730 0.852523 0.488391 0.168 Uiso 0.43(3) 1 calc R U P B 1
H16B H -0.515001 0.727581 0.500066 0.168 Uiso 0.43(3) 1 calc R U P B 1
H16C H -0.421127 0.700426 0.473036 0.168 Uiso 0.43(3) 1 calc R U P B 1
C16B C -0.4253(14) 0.653(3) 0.4910(5) 0.124(5) Uani 0.57(3) 1 d . U P B 2
H16D H -0.424869 0.714172 0.469935 0.187 Uiso 0.57(3) 1 calc R U P B 2
H16E H -0.498237 0.628511 0.496286 0.187 Uiso 0.57(3) 1 calc R U P B 2
H16F H -0.385376 0.568809 0.485926 0.187 Uiso 0.57(3) 1 calc R U P B 2
C17 C -0.0052(4) 0.8552(5) 0.59396(11) 0.0566(12) Uani 1 1 d . . . . .
H17A H 0.059478 0.908535 0.600279 0.068 Uiso 1 1 calc R U . . .
H17B H -0.066250 0.918342 0.595912 0.068 Uiso 1 1 calc R U . . .
C18 C 0.1977(3) 0.8474(4) 0.55109(10) 0.0382(9) Uani 1 1 d . . . . .
C19 C 0.2227(4) 0.9858(4) 0.55823(11) 0.0507(11) Uani 1 1 d . . . . .
H19 H 0.172866 1.056077 0.552188 0.061 Uiso 1 1 calc R U . . .
C20 C 0.3203(4) 1.0211(4) 0.57415(11) 0.0526(11) Uani 1 1 d . . . . .
H20 H 0.336523 1.115092 0.579113 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3947(3) 0.9173(4) 0.58288(10) 0.0434(10) Uani 1 1 d . . . . .
C22 C 0.3702(3) 0.7789(4) 0.57510(12) 0.0510(11) Uani 1 1 d . . . . .
H22 H 0.420739 0.708863 0.580490 0.061 Uiso 1 1 calc R U . . .
C23 C 0.2715(3) 0.7432(4) 0.55940(11) 0.0465(10) Uani 1 1 d . . . . .
H23 H 0.254935 0.649304 0.554458 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5840(3) 0.5653(4) 0.67572(10) 0.0393(9) Uani 1 1 d . . . . .
C25 C 0.6633(3) 0.4646(4) 0.67672(10) 0.0396(10) Uani 1 1 d . . . . .
C26 C 0.6136(3) 0.3324(4) 0.68498(10) 0.0367(9) Uani 1 1 d . . . . .
C27 C 0.5061(3) 0.3580(4) 0.68965(10) 0.0370(9) Uani 1 1 d . . . . .
C28 C 0.4164(3) 0.2625(4) 0.69777(10) 0.0401(10) Uani 1 1 d . . . . .
C29 C 0.3886(4) 0.1537(5) 0.67414(12) 0.0553(12) Uani 1 1 d . . . . .
H29 H 0.427119 0.140241 0.652832 0.066 Uiso 1 1 calc R U . . .
C30 C 0.3046(4) 0.0646(5) 0.68169(15) 0.0713(14) Uani 1 1 d . . . . .
H30 H 0.286973 -0.009048 0.665655 0.086 Uiso 1 1 calc R U . . .
C31 C 0.2471(4) 0.0846(6) 0.71281(16) 0.0720(15) Uani 1 1 d . . . . .
H31 H 0.189957 0.024980 0.717895 0.086 Uiso 1 1 calc R U . . .
C32 C 0.2737(4) 0.1924(5) 0.73643(14) 0.0627(13) Uani 1 1 d . . . . .
H32 H 0.234549 0.205594 0.757586 0.075 Uiso 1 1 calc R U . . .
C33 C 0.3572(3) 0.2807(5) 0.72927(11) 0.0510(11) Uani 1 1 d . . . . .
H33 H 0.374637 0.353524 0.745589 0.061 Uiso 1 1 calc R U . . .
C34 C 0.6613(3) 0.1914(4) 0.68421(11) 0.0431(10) Uani 1 1 d . . . . .
C35 C 0.7944(5) 0.0496(5) 0.65696(16) 0.0824(17) Uani 1 1 d . . . . .
H35A H 0.835033 0.052623 0.634553 0.099 Uiso 1 1 calc R U . . .
H35B H 0.736769 -0.018591 0.653396 0.099 Uiso 1 1 calc R U . . .
C36 C 0.8649(5) 0.0053(7) 0.68758(19) 0.117(2) Uani 1 1 d . . . . .
H36A H 0.924565 0.069338 0.690108 0.176 Uiso 1 1 calc R U . . .
H36B H 0.891267 -0.088027 0.682951 0.176 Uiso 1 1 calc R U . . .
H36C H 0.825383 0.005225 0.709916 0.176 Uiso 1 1 calc R U . . .
C37 C 0.7764(3) 0.5063(5) 0.67423(11) 0.0453(10) Uani 1 1 d . . . . .
C38 C 0.9532(3) 0.4820(6) 0.69882(14) 0.0717(15) Uani 1 1 d . . . . .
H38A H 0.957920 0.578962 0.707273 0.086 Uiso 1 1 calc R U . . .
H38B H 0.983417 0.476508 0.674515 0.086 Uiso 1 1 calc R U . . .
C39 C 1.0125(4) 0.3891(8) 0.72455(15) 0.100(2) Uani 1 1 d . . . . .
H39A H 0.980911 0.393766 0.748347 0.150 Uiso 1 1 calc R U . . .
H39B H 1.086419 0.418737 0.726624 0.150 Uiso 1 1 calc R U . . .
H39C H 1.009064 0.293957 0.715554 0.150 Uiso 1 1 calc R U . . .
C40 C 0.5919(4) 0.7185(4) 0.66690(12) 0.0501(11) Uani 1 1 d . . . . .
H40A H 0.528031 0.766539 0.675208 0.060 Uiso 1 1 calc R U . . .
H40B H 0.653977 0.758391 0.680051 0.060 Uiso 1 1 calc R U . . .
C41 C 0.3861(3) 0.5705(4) 0.68426(10) 0.0390(9) Uani 1 1 d . . . . .
C42 C 0.3195(3) 0.5669(4) 0.65384(11) 0.0483(11) Uani 1 1 d . . . . .
H42 H 0.340238 0.518132 0.632971 0.058 Uiso 1 1 calc R U . . .
C43 C 0.2207(3) 0.6355(5) 0.65362(11) 0.0503(11) Uani 1 1 d . . . . .
H43 H 0.175310 0.633136 0.632701 0.060 Uiso 1 1 calc R U . . .
C44 C 0.1906(3) 0.7066(4) 0.68445(11) 0.0412(10) Uani 1 1 d . . . . .
C45 C 0.2578(3) 0.7088(4) 0.71523(11) 0.0491(11) Uani 1 1 d . . . . .
H45 H 0.236800 0.756256 0.736270 0.059 Uiso 1 1 calc R U . . .
C46 C 0.3557(3) 0.6415(4) 0.71524(11) 0.0469(10) Uani 1 1 d . . . . .
H46 H 0.401249 0.643944 0.736122 0.056 Uiso 1 1 calc R U . . .
N1 N 0.0929(3) 0.8107(3) 0.53568(8) 0.0399(8) Uani 1 1 d . . . . .
N2 N 0.4886(2) 0.5004(3) 0.68396(8) 0.0385(8) Uani 1 1 d . . . . .
O1 O -0.1434(3) 0.5563(4) 0.46593(9) 0.0793(11) Uani 1 1 d . . . . .
O2 O -0.0616(3) 0.7228(3) 0.43397(8) 0.0631(9) Uani 1 1 d . U . . .
O3 O -0.2183(2) 0.7433(3) 0.57533(9) 0.0656(9) Uani 1 1 d . . . . .
O4 O -0.2612(2) 0.7432(4) 0.51515(9) 0.0698(9) Uani 1 1 d . U . . .
O5 O -0.0155(2) 0.7445(3) 0.61985(7) 0.0588(8) Uani 1 1 d . . . . .
H5 H -0.094205 0.708121 0.620109 0.088 Uiso 1 1 d R U . . .
O6 O 0.4899(2) 0.9592(3) 0.59902(8) 0.0586(8) Uani 1 1 d . . . . .
H6A H 0.528364 0.890067 0.602939 0.088 Uiso 1 1 calc R U . . .
O7 O 0.6234(2) 0.0874(3) 0.69798(8) 0.0599(8) Uani 1 1 d . . . . .
O8 O 0.7486(2) 0.1877(3) 0.66375(8) 0.0617(8) Uani 1 1 d . . . . .
O9 O 0.8065(2) 0.6009(4) 0.65462(9) 0.0680(9) Uani 1 1 d . . . . .
O10 O 0.8415(2) 0.4360(3) 0.69726(8) 0.0552(8) Uani 1 1 d . . . . .
O11 O 0.6018(2) 0.7413(3) 0.62832(9) 0.0563(8) Uani 1 1 d . . . . .
H11 H 0.660(4) 0.718(6) 0.6227(14) 0.084 Uiso 1 1 d . U . . .
O12 O 0.0955(2) 0.7793(3) 0.68552(8) 0.0556(8) Uani 1 1 d . . . . .
H12 H 0.059(4) 0.765(5) 0.6622(13) 0.083 Uiso 1 1 d . 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
C1 C2 1.360(5) . ?
C1 N1 1.379(5) . ?
C1 C5 1.480(5) . ?
C2 C3 1.435(5) . ?
C2 C11 1.471(6) . ?
C3 C4 1.379(5) . ?
C3 C14 1.463(6) . ?
C4 N1 1.368(5) . ?
C4 C17 1.482(5) . ?
C5 C6 1.373(6) . ?
C5 C10 1.379(5) . ?
C6 C7 1.387(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.193(5) . ?
C11 O2 1.333(5) . ?
C12 C13B 1.27(3) . ?
C12 O2 1.445(5) . ?
C12 C13A 1.456(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14 O3 1.205(5) . ?
C14 O4 1.317(5) . ?
C15 C16A 1.361(18) . ?
C15 O4 1.459(6) . ?
C15 C16B 1.482(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17 O5 1.416(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.371(5) . ?
C18 C23 1.374(5) . ?
C18 N1 1.442(5) . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(6) . ?
C20 H20 0.9300 . ?
C21 O6 1.361(5) . ?
C21 C22 1.373(6) . ?
C22 C23 1.376(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.371(5) . ?
C24 N2 1.375(5) . ?
C24 C40 1.492(5) . ?
C25 C26 1.434(5) . ?
C25 C37 1.464(5) . ?
C26 C27 1.372(5) . ?
C26 C34 1.462(5) . ?
C27 N2 1.382(5) . ?
C27 C28 1.472(5) . ?
C28 C29 1.378(6) . ?
C28 C33 1.388(5) . ?
C29 C30 1.376(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.367(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.364(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 O7 1.208(5) . ?
C34 O8 1.333(5) . ?
C35 O8 1.452(5) . ?
C35 C36 1.453(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O9 1.211(5) . ?
C37 O10 1.323(5) . ?
C38 O10 1.453(5) . ?
C38 C39 1.464(7) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 O11 1.424(5) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.357(5) . ?
C41 C46 1.373(5) . ?
C41 N2 1.436(5) . ?
C42 C43 1.388(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.367(5) . ?
C43 H43 0.9300 . ?
C44 O12 1.369(5) . ?
C44 C45 1.371(5) . ?
C45 C46 1.373(5) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
O5 H5 1.0362 . ?
O6 H6A 0.8200 . ?
O11 H11 0.79(5) . ?
O12 H12 0.95(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 107.7(3) . . ?
C2 C1 C5 130.8(3) . . ?
N1 C1 C5 121.5(3) . . ?
C1 C2 C3 107.7(3) . . ?
C1 C2 C11 125.4(4) . . ?
C3 C2 C11 126.7(4) . . ?
C4 C3 C2 106.9(4) . . ?
C4 C3 C14 122.0(4) . . ?
C2 C3 C14 130.9(4) . . ?
N1 C4 C3 107.7(3) . . ?
N1 C4 C17 123.2(4) . . ?
C3 C4 C17 129.1(4) . . ?
C6 C5 C10 118.9(4) . . ?
C6 C5 C1 120.6(4) . . ?
C10 C5 C1 120.5(4) . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 119.7(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.5(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 119.8(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C5 C10 C9 120.3(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
O1 C11 O2 123.2(4) . . ?
O1 C11 C2 125.8(4) . . ?
O2 C11 C2 111.0(4) . . ?
C13B C12 O2 118.4(18) . . ?
O2 C12 C13A 107.0(9) . . ?
O2 C12 H12A 110.3 . . ?
C13A C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C13A C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C13B C12 H12C 107.7 . . ?
O2 C12 H12C 107.7 . . ?
C13B C12 H12D 107.7 . . ?
O2 C12 H12D 107.7 . . ?
H12C C12 H12D 107.1 . . ?
C12 C13A H13A 109.5 . . ?
C12 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C12 C13B H13D 109.5 . . ?
C12 C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12 C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O3 C14 O4 124.1(4) . . ?
O3 C14 C3 123.6(4) . . ?
O4 C14 C3 112.2(4) . . ?
C16A C15 O4 113.6(9) . . ?
O4 C15 C16B 106.1(8) . . ?
C16A C15 H15A 108.8 . . ?
O4 C15 H15A 108.8 . . ?
C16A C15 H15B 108.8 . . ?
O4 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O4 C15 H15C 110.5 . . ?
C16B C15 H15C 110.5 . . ?
O4 C15 H15D 110.5 . . ?
C16B C15 H15D 110.5 . . ?
H15C C15 H15D 108.7 . . ?
C15 C16A H16A 109.5 . . ?
C15 C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15 C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15 C16B H16D 109.5 . . ?
C15 C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15 C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
O5 C17 C4 113.9(4) . . ?
O5 C17 H17A 108.8 . . ?
C4 C17 H17A 108.8 . . ?
O5 C17 H17B 108.8 . . ?
C4 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C23 120.1(4) . . ?
C19 C18 N1 120.0(4) . . ?
C23 C18 N1 119.9(3) . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
O6 C21 C22 123.4(4) . . ?
O6 C21 C20 117.1(4) . . ?
C22 C21 C20 119.5(4) . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.5(4) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 N2 107.8(3) . . ?
C25 C24 C40 129.2(4) . . ?
N2 C24 C40 123.0(3) . . ?
C24 C25 C26 107.5(3) . . ?
C24 C25 C37 120.0(4) . . ?
C26 C25 C37 132.0(4) . . ?
C27 C26 C25 107.3(3) . . ?
C27 C26 C34 124.1(4) . . ?
C25 C26 C34 128.1(3) . . ?
C26 C27 N2 107.6(3) . . ?
C26 C27 C28 131.3(3) . . ?
N2 C27 C28 121.0(3) . . ?
C29 C28 C33 118.5(4) . . ?
C29 C28 C27 120.8(4) . . ?
C33 C28 C27 120.8(4) . . ?
C30 C29 C28 120.8(4) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 119.9(5) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C32 C31 C30 119.9(5) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C33 C32 C31 120.7(5) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C28 120.3(4) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
O7 C34 O8 122.9(4) . . ?
O7 C34 C26 125.1(4) . . ?
O8 C34 C26 111.8(4) . . ?
O8 C35 C36 111.2(5) . . ?
O8 C35 H35A 109.4 . . ?
C36 C35 H35A 109.4 . . ?
O8 C35 H35B 109.4 . . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O9 C37 O10 123.4(4) . . ?
O9 C37 C25 123.4(4) . . ?
O10 C37 C25 113.1(4) . . ?
O10 C38 C39 107.7(4) . . ?
O10 C38 H38A 110.2 . . ?
C39 C38 H38A 110.2 . . ?
O10 C38 H38B 110.2 . . ?
C39 C38 H38B 110.2 . . ?
H38A C38 H38B 108.5 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O11 C40 C24 111.5(3) . . ?
O11 C40 H40A 109.3 . . ?
C24 C40 H40A 109.3 . . ?
O11 C40 H40B 109.3 . . ?
C24 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C42 C41 C46 120.1(4) . . ?
C42 C41 N2 119.9(3) . . ?
C46 C41 N2 120.0(3) . . ?
C41 C42 C43 120.5(4) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C44 C43 C42 119.4(4) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 O12 122.0(4) . . ?
C43 C44 C45 119.9(4) . . ?
O12 C44 C45 118.1(3) . . ?
C44 C45 C46 120.5(4) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C41 C46 C45 119.6(4) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?
C4 N1 C1 110.0(3) . . ?
C4 N1 C18 124.6(3) . . ?
C1 N1 C18 125.2(3) . . ?
C24 N2 C27 109.7(3) . . ?
C24 N2 C41 124.3(3) . . ?
C27 N2 C41 125.8(3) . . ?
C11 O2 C12 115.6(4) . . ?
C14 O4 C15 116.7(4) . . ?
C17 O5 H5 111.0 . . ?
C21 O6 H6A 109.5 . . ?
C34 O8 C35 116.6(4) . . ?
C37 O10 C38 115.8(4) . . ?
C40 O11 H11 109(4) . . ?
C44 O12 H12 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.8(4) . . . . ?
C5 C1 C2 C3 178.8(4) . . . . ?
N1 C1 C2 C11 -174.2(4) . . . . ?
C5 C1 C2 C11 3.8(7) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C11 C2 C3 C4 174.5(4) . . . . ?
C1 C2 C3 C14 174.3(4) . . . . ?
C11 C2 C3 C14 -10.8(7) . . . . ?
C2 C3 C4 N1 -0.2(4) . . . . ?
C14 C3 C4 N1 -175.4(3) . . . . ?
C2 C3 C4 C17 178.7(4) . . . . ?
C14 C3 C4 C17 3.4(7) . . . . ?
C2 C1 C5 C6 128.3(5) . . . . ?
N1 C1 C5 C6 -53.9(5) . . . . ?
C2 C1 C5 C10 -50.0(6) . . . . ?
N1 C1 C5 C10 127.8(4) . . . . ?
C10 C5 C6 C7 -1.2(7) . . . . ?
C1 C5 C6 C7 -179.5(4) . . . . ?
C5 C6 C7 C8 0.7(8) . . . . ?
C6 C7 C8 C9 0.7(8) . . . . ?
C7 C8 C9 C10 -1.6(8) . . . . ?
C6 C5 C10 C9 0.3(7) . . . . ?
C1 C5 C10 C9 178.6(4) . . . . ?
C8 C9 C10 C5 1.1(7) . . . . ?
C1 C2 C11 O1 131.7(5) . . . . ?
C3 C2 C11 O1 -42.3(7) . . . . ?
C1 C2 C11 O2 -47.9(5) . . . . ?
C3 C2 C11 O2 138.1(4) . . . . ?
C4 C3 C14 O3 -21.9(6) . . . . ?
C2 C3 C14 O3 164.1(4) . . . . ?
C4 C3 C14 O4 156.3(4) . . . . ?
C2 C3 C14 O4 -17.7(6) . . . . ?
N1 C4 C17 O5 -108.0(4) . . . . ?
C3 C4 C17 O5 73.3(6) . . . . ?
C23 C18 C19 C20 -1.0(6) . . . . ?
N1 C18 C19 C20 177.5(4) . . . . ?
C18 C19 C20 C21 0.5(7) . . . . ?
C19 C20 C21 O6 -179.4(4) . . . . ?
C19 C20 C21 C22 0.6(6) . . . . ?
O6 C21 C22 C23 178.7(4) . . . . ?
C20 C21 C22 C23 -1.3(6) . . . . ?
C19 C18 C23 C22 0.4(6) . . . . ?
N1 C18 C23 C22 -178.1(3) . . . . ?
C21 C22 C23 C18 0.8(6) . . . . ?
N2 C24 C25 C26 1.5(4) . . . . ?
C40 C24 C25 C26 -177.4(4) . . . . ?
N2 C24 C25 C37 -171.3(3) . . . . ?
C40 C24 C25 C37 9.8(6) . . . . ?
C24 C25 C26 C27 -1.5(4) . . . . ?
C37 C25 C26 C27 170.1(4) . . . . ?
C24 C25 C26 C34 171.1(4) . . . . ?
C37 C25 C26 C34 -17.3(7) . . . . ?
C25 C26 C27 N2 0.9(4) . . . . ?
C34 C26 C27 N2 -172.1(3) . . . . ?
C25 C26 C27 C28 178.7(4) . . . . ?
C34 C26 C27 C28 5.7(7) . . . . ?
C26 C27 C28 C29 -60.0(6) . . . . ?
N2 C27 C28 C29 117.6(4) . . . . ?
C26 C27 C28 C33 120.5(5) . . . . ?
N2 C27 C28 C33 -61.9(5) . . . . ?
C33 C28 C29 C30 -0.3(6) . . . . ?
C27 C28 C29 C30 -179.9(4) . . . . ?
C28 C29 C30 C31 0.6(7) . . . . ?
C29 C30 C31 C32 -0.4(8) . . . . ?
C30 C31 C32 C33 0.1(8) . . . . ?
C31 C32 C33 C28 0.1(7) . . . . ?
C29 C28 C33 C32 0.0(6) . . . . ?
C27 C28 C33 C32 179.5(4) . . . . ?
C27 C26 C34 O7 -23.4(6) . . . . ?
C25 C26 C34 O7 165.1(4) . . . . ?
C27 C26 C34 O8 151.6(4) . . . . ?
C25 C26 C34 O8 -20.0(6) . . . . ?
C24 C25 C37 O9 -37.8(6) . . . . ?
C26 C25 C37 O9 151.5(4) . . . . ?
C24 C25 C37 O10 138.3(4) . . . . ?
C26 C25 C37 O10 -32.4(6) . . . . ?
C25 C24 C40 O11 75.2(5) . . . . ?
N2 C24 C40 O11 -103.6(4) . . . . ?
C46 C41 C42 C43 0.4(6) . . . . ?
N2 C41 C42 C43 -179.3(4) . . . . ?
C41 C42 C43 C44 -0.2(6) . . . . ?
C42 C43 C44 O12 178.2(4) . . . . ?
C42 C43 C44 C45 -0.4(6) . . . . ?
C43 C44 C45 C46 0.8(6) . . . . ?
O12 C44 C45 C46 -177.9(4) . . . . ?
C42 C41 C46 C45 0.0(6) . . . . ?
N2 C41 C46 C45 179.7(4) . . . . ?
C44 C45 C46 C41 -0.5(6) . . . . ?
C3 C4 N1 C1 0.7(4) . . . . ?
C17 C4 N1 C1 -178.3(4) . . . . ?
C3 C4 N1 C18 -174.0(3) . . . . ?
C17 C4 N1 C18 7.0(6) . . . . ?
C2 C1 N1 C4 -0.9(4) . . . . ?
C5 C1 N1 C4 -179.1(3) . . . . ?
C2 C1 N1 C18 173.7(3) . . . . ?
C5 C1 N1 C18 -4.5(5) . . . . ?
C19 C18 N1 C4 -76.5(5) . . . . ?
C23 C18 N1 C4 102.0(4) . . . . ?
C19 C18 N1 C1 109.6(4) . . . . ?
C23 C18 N1 C1 -71.9(5) . . . . ?
C25 C24 N2 C27 -1.0(4) . . . . ?
C40 C24 N2 C27 178.0(3) . . . . ?
C25 C24 N2 C41 -177.5(3) . . . . ?
C40 C24 N2 C41 1.5(6) . . . . ?
C26 C27 N2 C24 0.0(4) . . . . ?
C28 C27 N2 C24 -178.0(3) . . . . ?
C26 C27 N2 C41 176.5(3) . . . . ?
C28 C27 N2 C41 -1.6(6) . . . . ?
C42 C41 N2 C24 94.7(5) . . . . ?
C46 C41 N2 C24 -85.0(5) . . . . ?
C42 C41 N2 C27 -81.2(5) . . . . ?
C46 C41 N2 C27 99.0(5) . . . . ?
O1 C11 O2 C12 -5.7(7) . . . . ?
C2 C11 O2 C12 173.9(4) . . . . ?
C13B C12 O2 C11 142(3) . . . . ?
C13A C12 O2 C11 174.9(11) . . . . ?
O3 C14 O4 C15 -5.3(7) . . . . ?
C3 C14 O4 C15 176.5(4) . . . . ?
C16A C15 O4 C14 167.3(18) . . . . ?
C16B C15 O4 C14 -150.4(12) . . . . ?
O7 C34 O8 C35 3.0(6) . . . . ?
C26 C34 O8 C35 -172.1(4) . . . . ?
C36 C35 O8 C34 -83.2(6) . . . . ?
O9 C37 O10 C38 2.0(6) . . . . ?
C25 C37 O10 C38 -174.1(4) . . . . ?
C39 C38 O10 C37 -178.0(4) . . . . ?

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
C19 H19 O2 0.93 2.57 3.427(5) 153.6 3_576 yes
C23 H23 O1 0.93 2.49 3.368(5) 157.6 3_566 yes
C36 H36C O7 0.96 2.65 3.131(7) 111.6 . yes
C43 H43 O5 0.93 2.62 3.305(5) 130.9 . yes
C46 H46 O7 0.93 2.48 3.189(5) 133.5 2_656 yes
O5 H5 O3 1.04 2.23 2.945(4) 125.0 . yes
O5 H5 O9 1.04 2.05 2.916(4) 139.0 1_455 yes
O6 H6A O11 0.82 1.90 2.688(4) 160.7 . yes
O11 H11 O3 0.79(5) 2.34(5) 2.993(4) 141(5) 1_655 yes
O11 H11 O9 0.79(5) 2.40(5) 2.997(4) 134(5) . yes
O12 H12 O5 0.95(5) 1.78(5) 2.731(4) 176(4) . yes

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049



