# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_y
_database_code_depnum_ccdc_archive 'CCDC 2361585'
loop_
_audit_author_name
_audit_author_address
'Weijun Yao'
;Zhejiang SciTech University
China
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 Br N O5'
_chemical_formula_sum            'C25 H22 Br N O5'
_chemical_formula_weight         496.34
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.958(4)
_cell_length_b                   13.864(6)
_cell_length_c                   9.026(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.036(8)
_cell_angle_gamma                90
_cell_volume                     1120.3(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4355
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.694
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                2475
_reflns_number_total             3275
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1A(0.214) H1B(0.214) H1C(0.214) H2A(0.135) H2B(0.135) H7(0.055)
 H8(0.064) H9A(0.073) H9B(0.073) H10A(0.081) H10B(0.081) H12(0.067) H13(0.082)
 H14(0.081) H15(0.079) H16(0.07) H20(0.052) H22(0.064) H23(0.065) H25A(0.143)
 H25B(0.143) H25C(0.143)
 Fixed X: H1A(0.709992) H1B(0.853079) H1C(0.697089) H2A(0.830708)
 H2B(0.846479) H7(0.171366) H8(0.352121) H9A(0.665428) H9B(0.541842)
 H10A(0.362465) H10B(0.495388) H12(0.23283) H13(0.057447) H14(-0.176207) H15(-
 0.231066) H16(-0.061531) H20(0.470086) H22(0.355423) H23(0.208612)
 H25A(0.051268) H25B(-0.068283) H25C(-0.072387)
 Fixed Y: H1A(0.544208) H1B(0.48076) H1C(0.43144) H2A(0.423792) H2B(0.53656)
 H7(0.601803) H8(0.482471) H9A(0.621946) H9B(0.632478) H10A(0.772768)
 H10B(0.755066) H12(0.354113) H13(0.236715) H14(0.280576) H15(0.439212)
 H16(0.557938) H20(0.410665) H22(0.332576) H23(0.471843) H25A(0.791747)
 H25B(0.720725) H25C(0.748473)
 Fixed Z: H1A(0.952581) H1B(0.980598) H1C(0.952961) H2A(0.752465)
 H2B(0.752616) H7(0.508812) H8(0.643477) H9A(0.30477) H9B(0.174177)
 H10A(0.394613) H10B(0.51387) H12(0.498565) H13(0.436347) H14(0.353185)
 H15(0.314155) H16(0.372056) H20(0.319706) H22(-0.098224) H23(-0.127392)
 H25A(0.023506) H25B(0.084142) H25C(-0.084322)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54432(7) 0.24680(5) 0.13106(7) 0.0715(3) Uani 1 1 d . . . . .
O1 O 0.1024(6) 0.6183(4) -0.1515(6) 0.0785(14) Uani 1 1 d . . . . .
O2 O 0.7191(6) 0.6262(4) 0.5843(6) 0.0866(16) Uani 1 1 d . . . . .
O3 O 0.1403(5) 0.7229(3) 0.2763(5) 0.0786(15) Uani 1 1 d . . . . .
O4 O 0.5623(5) 0.7520(5) 0.3024(5) 0.0895(14) Uani 1 1 d . . . . .
O5 O 0.6394(6) 0.4917(5) 0.6924(6) 0.0921(18) Uani 1 1 d . . . . .
N1 N 0.1743(5) 0.6107(3) 0.0903(5) 0.0476(12) Uani 1 1 d . . . . .
C1 C 0.7587(12) 0.4851(12) 0.9272(10) 0.143(5) Uani 1 1 d . . . . .
H1A H 0.709992 0.544208 0.952581 0.214 Uiso 1 1 calc R U . . .
H1B H 0.853079 0.480760 0.980598 0.214 Uiso 1 1 calc R U . . .
H1C H 0.697089 0.431440 0.952961 0.214 Uiso 1 1 calc R U . . .
C2 C 0.7815(11) 0.4835(8) 0.7781(11) 0.112(3) Uani 1 1 d . . . . .
H2A H 0.830708 0.423792 0.752465 0.135 Uiso 1 1 calc R U . . .
H2B H 0.846479 0.536560 0.752616 0.135 Uiso 1 1 calc R U . . .
C3 C 0.6246(8) 0.5680(5) 0.6016(7) 0.0565(16) Uani 1 1 d . . . . .
C4 C 0.4794(7) 0.5669(4) 0.5220(6) 0.0482(15) Uani 1 1 d . . . . .
C5 C 0.4466(6) 0.6290(4) 0.3855(6) 0.0430(14) Uani 1 1 d . . . . .
C6 C 0.2996(6) 0.5838(4) 0.3224(6) 0.0411(13) Uani 1 1 d . . . . .
C7 C 0.2221(6) 0.5467(4) 0.4648(6) 0.0460(15) Uani 1 1 d . . . . .
H7 H 0.171366 0.601803 0.508812 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3556(7) 0.5235(5) 0.5622(6) 0.0531(16) Uani 1 1 d . . . . .
H8 H 0.352121 0.482471 0.643477 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5697(7) 0.6500(5) 0.2754(7) 0.0609(17) Uani 1 1 d . . . . .
H9A H 0.665428 0.621946 0.304770 0.073 Uiso 1 1 calc R U . . .
H9B H 0.541842 0.632478 0.174177 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4560(7) 0.7393(6) 0.4153(7) 0.0671(17) Uani 1 1 d . . . . .
H10A H 0.362465 0.772768 0.394613 0.081 Uiso 1 1 calc R U . . .
H10B H 0.495388 0.755066 0.513870 0.081 Uiso 1 1 calc R U . . .
C11 C 0.1079(6) 0.4692(4) 0.4371(6) 0.0471(15) Uani 1 1 d . . . . .
C12 C 0.1395(7) 0.3722(5) 0.4596(7) 0.0556(16) Uani 1 1 d . . . . .
H12 H 0.232830 0.354113 0.498565 0.067 Uiso 1 1 calc R U . . .
C13 C 0.0334(8) 0.3016(5) 0.4246(8) 0.0681(19) Uani 1 1 d . . . . .
H13 H 0.057447 0.236715 0.436347 0.082 Uiso 1 1 calc R U . . .
C14 C -0.1041(8) 0.3274(5) 0.3736(8) 0.0672(18) Uani 1 1 d . . . . .
H14 H -0.176207 0.280576 0.353185 0.081 Uiso 1 1 calc R U . . .
C15 C -0.1368(7) 0.4223(5) 0.3521(8) 0.0662(18) Uani 1 1 d . . . . .
H15 H -0.231066 0.439212 0.314155 0.079 Uiso 1 1 calc R U . . .
C16 C -0.0351(7) 0.4935(5) 0.3848(7) 0.0586(17) Uani 1 1 d . . . . .
H16 H -0.061531 0.557938 0.372056 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1954(6) 0.6499(4) 0.2313(6) 0.0501(15) Uani 1 1 d . . . . .
C18 C 0.2555(6) 0.5219(4) 0.0801(6) 0.0398(15) Uani 1 1 d . . . . .
C19 C 0.3315(6) 0.5037(4) 0.2140(6) 0.0371(14) Uani 1 1 d . . . . .
C20 C 0.4177(6) 0.4232(4) 0.2310(6) 0.0435(13) Uani 1 1 d . . . . .
H20 H 0.470086 0.410665 0.319706 0.052 Uiso 1 1 calc R U . . .
C21 C 0.4246(6) 0.3605(4) 0.1114(7) 0.0450(14) Uani 1 1 d . . . . .
C22 C 0.3486(7) 0.3765(5) -0.0209(7) 0.0533(16) Uani 1 1 d . . . . .
H22 H 0.355423 0.332576 -0.098224 0.064 Uiso 1 1 calc R U . . .
C23 C 0.2612(7) 0.4593(5) -0.0388(7) 0.0545(16) Uani 1 1 d . . . . .
H23 H 0.208612 0.471843 -0.127392 0.065 Uiso 1 1 calc R U . . .
C24 C 0.0914(7) 0.6521(5) -0.0303(8) 0.0565(16) Uani 1 1 d . . . . .
C25 C -0.0085(9) 0.7358(7) 0.0011(9) 0.095(3) Uani 1 1 d . . . . .
H25A H 0.051268 0.791747 0.023506 0.143 Uiso 1 1 calc R U . . .
H25B H -0.068283 0.720725 0.084142 0.143 Uiso 1 1 calc R U . . .
H25C H -0.072387 0.748473 -0.084322 0.143 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
Br1 C21 1.911(5) . ?
O1 C24 1.197(7) . ?
O2 C3 1.184(7) . ?
O3 C17 1.203(7) . ?
O4 C9 1.436(9) . ?
O4 C10 1.430(7) . ?
O5 C2 1.470(9) . ?
O5 C3 1.342(8) . ?
N1 C17 1.391(7) . ?
N1 C18 1.435(7) . ?
N1 C24 1.417(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.369(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.464(9) . ?
C4 C5 1.523(8) . ?
C4 C8 1.323(8) . ?
C5 C6 1.549(8) . ?
C5 C9 1.538(7) . ?
C5 C10 1.554(10) . ?
C6 C7 1.569(7) . ?
C6 C17 1.526(8) . ?
C6 C19 1.514(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.494(8) . ?
C7 C11 1.499(8) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.388(8) . ?
C11 C16 1.391(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.348(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(9) . ?
C16 H16 0.9300 . ?
C18 C19 1.389(8) . ?
C18 C23 1.382(8) . ?
C19 C20 1.363(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(8) . ?
C21 C22 1.372(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.395(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.498(10) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O4 C9 92.1(5) . . ?
C3 O5 C2 116.5(6) . . ?
C17 N1 C18 109.9(5) . . ?
C17 N1 C24 126.6(5) . . ?
C24 N1 C18 123.5(5) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O5 C2 H2A 109.4 . . ?
O5 C2 H2B 109.4 . . ?
C1 C2 O5 111.1(9) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O2 C3 O5 124.2(7) . . ?
O2 C3 C4 124.7(6) . . ?
O5 C3 C4 111.0(6) . . ?
C3 C4 C5 122.3(5) . . ?
C8 C4 C3 127.5(6) . . ?
C8 C4 C5 109.9(6) . . ?
C4 C5 C6 101.9(4) . . ?
C4 C5 C9 120.5(5) . . ?
C4 C5 C10 114.1(5) . . ?
C6 C5 C10 120.1(5) . . ?
C9 C5 C6 117.3(5) . . ?
C9 C5 C10 83.7(4) . . ?
C5 C6 C7 103.1(4) . . ?
C17 C6 C5 116.8(5) . . ?
C17 C6 C7 111.0(4) . . ?
C19 C6 C5 110.9(4) . . ?
C19 C6 C7 112.9(4) . . ?
C19 C6 C17 102.6(5) . . ?
C6 C7 H7 107.6 . . ?
C8 C7 C6 100.6(4) . . ?
C8 C7 H7 107.6 . . ?
C11 C7 C6 114.7(5) . . ?
C11 C7 H7 107.6 . . ?
C11 C7 C8 118.1(5) . . ?
C4 C8 C7 113.7(5) . . ?
C4 C8 H8 123.2 . . ?
C7 C8 H8 123.2 . . ?
O4 C9 C5 92.2(4) . . ?
O4 C9 H9A 113.3 . . ?
O4 C9 H9B 113.3 . . ?
C5 C9 H9A 113.3 . . ?
C5 C9 H9B 113.3 . . ?
H9A C9 H9B 110.6 . . ?
O4 C10 C5 91.7(5) . . ?
O4 C10 H10A 113.3 . . ?
O4 C10 H10B 113.3 . . ?
C5 C10 H10A 113.3 . . ?
C5 C10 H10B 113.3 . . ?
H10A C10 H10B 110.7 . . ?
C12 C11 C7 122.4(5) . . ?
C12 C11 C16 117.7(5) . . ?
C16 C11 C7 119.9(5) . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(6) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.0 . . ?
C14 C15 C16 121.9(6) . . ?
C16 C15 H15 119.0 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.8(6) . . ?
C15 C16 H16 120.1 . . ?
O3 C17 N1 126.3(6) . . ?
O3 C17 C6 125.0(5) . . ?
N1 C17 C6 108.6(5) . . ?
C19 C18 N1 109.5(5) . . ?
C23 C18 N1 128.4(6) . . ?
C23 C18 C19 122.1(5) . . ?
C18 C19 C6 109.4(5) . . ?
C20 C19 C6 130.3(6) . . ?
C20 C19 C18 120.3(5) . . ?
C19 C20 H20 121.1 . . ?
C19 C20 C21 117.8(6) . . ?
C21 C20 H20 121.1 . . ?
C20 C21 Br1 119.0(5) . . ?
C22 C21 Br1 118.3(4) . . ?
C22 C21 C20 122.8(5) . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(5) . . ?
C23 C22 H22 120.2 . . ?
C18 C23 C22 117.6(6) . . ?
C18 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
O1 C24 N1 119.0(6) . . ?
O1 C24 C25 123.0(7) . . ?
N1 C24 C25 117.9(6) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C21 C22 C23 -179.6(4) . . . . ?
O2 C3 C4 C5 12.8(10) . . . . ?
O2 C3 C4 C8 -159.1(7) . . . . ?
O5 C3 C4 C5 -164.4(6) . . . . ?
O5 C3 C4 C8 23.7(9) . . . . ?
N1 C18 C19 C6 0.6(6) . . . . ?
N1 C18 C19 C20 -179.6(5) . . . . ?
N1 C18 C23 C22 -179.7(5) . . . . ?
C2 O5 C3 O2 2.1(11) . . . . ?
C2 O5 C3 C4 179.3(7) . . . . ?
C3 O5 C2 C1 119.6(11) . . . . ?
C3 C4 C5 C6 166.4(5) . . . . ?
C3 C4 C5 C9 34.5(8) . . . . ?
C3 C4 C5 C10 -62.6(7) . . . . ?
C3 C4 C8 C7 172.9(5) . . . . ?
C4 C5 C6 C7 31.1(5) . . . . ?
C4 C5 C6 C17 153.0(5) . . . . ?
C4 C5 C6 C19 -90.0(5) . . . . ?
C4 C5 C9 O4 -118.3(5) . . . . ?
C4 C5 C10 O4 124.7(5) . . . . ?
C5 C4 C8 C7 0.2(7) . . . . ?
C5 C6 C7 C8 -30.6(5) . . . . ?
C5 C6 C7 C11 -158.5(5) . . . . ?
C5 C6 C17 O3 -59.6(7) . . . . ?
C5 C6 C17 N1 121.1(5) . . . . ?
C5 C6 C19 C18 -125.5(5) . . . . ?
C5 C6 C19 C20 54.7(7) . . . . ?
C6 C5 C9 O4 116.7(5) . . . . ?
C6 C5 C10 O4 -114.0(5) . . . . ?
C6 C7 C8 C4 19.8(6) . . . . ?
C6 C7 C11 C12 99.0(6) . . . . ?
C6 C7 C11 C16 -80.0(6) . . . . ?
C6 C19 C20 C21 179.0(5) . . . . ?
C7 C6 C17 O3 58.1(7) . . . . ?
C7 C6 C17 N1 -121.2(5) . . . . ?
C7 C6 C19 C18 119.4(5) . . . . ?
C7 C6 C19 C20 -60.4(8) . . . . ?
C7 C11 C12 C13 -176.2(5) . . . . ?
C7 C11 C16 C15 176.5(6) . . . . ?
C8 C4 C5 C6 -20.4(6) . . . . ?
C8 C4 C5 C9 -152.3(5) . . . . ?
C8 C4 C5 C10 110.6(6) . . . . ?
C8 C7 C11 C12 -19.5(7) . . . . ?
C8 C7 C11 C16 161.6(5) . . . . ?
C9 O4 C10 C5 -4.3(5) . . . . ?
C9 C5 C6 C7 164.9(5) . . . . ?
C9 C5 C6 C17 -73.2(6) . . . . ?
C9 C5 C6 C19 43.8(7) . . . . ?
C9 C5 C10 O4 4.0(5) . . . . ?
C10 O4 C9 C5 4.4(5) . . . . ?
C10 C5 C6 C7 -96.1(5) . . . . ?
C10 C5 C6 C17 25.8(7) . . . . ?
C10 C5 C6 C19 142.9(5) . . . . ?
C10 C5 C9 O4 -4.0(5) . . . . ?
C11 C7 C8 C4 145.4(5) . . . . ?
C11 C12 C13 C14 -2.6(10) . . . . ?
C12 C11 C16 C15 -2.5(9) . . . . ?
C12 C13 C14 C15 2.1(11) . . . . ?
C13 C14 C15 C16 -1.9(11) . . . . ?
C14 C15 C16 C11 2.1(10) . . . . ?
C16 C11 C12 C13 2.8(8) . . . . ?
C17 N1 C18 C19 -0.8(6) . . . . ?
C17 N1 C18 C23 178.1(5) . . . . ?
C17 N1 C24 O1 168.1(6) . . . . ?
C17 N1 C24 C25 -13.0(9) . . . . ?
C17 C6 C7 C8 -156.4(5) . . . . ?
C17 C6 C7 C11 75.7(6) . . . . ?
C17 C6 C19 C18 -0.1(5) . . . . ?
C17 C6 C19 C20 -179.9(6) . . . . ?
C18 N1 C17 O3 -178.5(6) . . . . ?
C18 N1 C17 C6 0.8(6) . . . . ?
C18 N1 C24 O1 -8.9(9) . . . . ?
C18 N1 C24 C25 170.0(6) . . . . ?
C18 C19 C20 C21 -0.8(8) . . . . ?
C19 C6 C7 C8 89.1(5) . . . . ?
C19 C6 C7 C11 -38.8(7) . . . . ?
C19 C6 C17 O3 178.8(6) . . . . ?
C19 C6 C17 N1 -0.4(5) . . . . ?
C19 C18 C23 C22 -0.9(8) . . . . ?
C19 C20 C21 Br1 180.0(4) . . . . ?
C19 C20 C21 C22 -0.1(8) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C21 C22 C23 C18 0.0(8) . . . . ?
C23 C18 C19 C6 -178.4(5) . . . . ?
C23 C18 C19 C20 1.4(8) . . . . ?
C24 N1 C17 O3 4.2(9) . . . . ?
C24 N1 C17 C6 -176.6(5) . . . . ?
C24 N1 C18 C19 176.6(5) . . . . ?
C24 N1 C18 C23 -4.5(8) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_220628_hj3_110132_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2361586'
loop_
_audit_author_name
_audit_author_address
'Weijun Yao'
;Zhejiang SciTech University
China
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 N O6'
_chemical_formula_weight         476.53

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.8531(5)
_cell_length_b                   8.9782(6)
_cell_length_c                   35.617(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9413
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      69.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.722
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27527
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         70.086
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4661
_reflns_number_gt                4385
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2300P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4661
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2937
_refine_ls_wR_factor_gt          0.2854
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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 0.7639(6) 0.1218(4) 0.20049(9) 0.0488(10) Uani 1 1 d . . . . .
C1 C 0.5794(14) 0.1069(17) 0.2556(3) 0.106(4) Uani 1 1 d . . . . .
H1 H 0.566521 0.215271 0.256762 0.128 Uiso 1 1 d R U . . .
H5 H 0.566770 0.064661 0.280792 0.128 Uiso 1 1 d R U . . .
H6 H 0.491881 0.064631 0.239002 0.128 Uiso 1 1 d R U . . .
H35 H 0.495661 0.151061 0.237332 0.128 Uiso 1 1 d R U . . .
O6 O 1.0739(6) 0.2799(6) 0.03831(13) 0.0665(13) Uani 1 1 d . . . . .
O5 O 0.7936(6) 0.0528(4) 0.12852(9) 0.0452(9) Uani 1 1 d . . . . .
C6 C 0.7629(6) 0.1845(5) 0.12557(11) 0.0337(9) Uani 1 1 d . . . . .
O2 O 0.7676(13) 0.3590(5) 0.21607(10) 0.100(3) Uani 1 1 d . . . . .
C2 C 0.7459(9) 0.0640(6) 0.23913(13) 0.0507(14) Uani 1 1 d . . . . .
O3 O 0.6810(6) -0.1355(4) 0.00464(10) 0.0498(9) Uani 1 1 d . . . . .
C3 C 0.750(3) -0.0999(9) 0.2321(2) 0.137(8) Uani 1 1 d . . . . .
H3 H 0.633987 -0.135797 0.227433 0.205 Uiso 1 1 calc R U . . .
H29 H 0.796809 -0.150727 0.254188 0.205 Uiso 1 1 calc R U . . .
H30 H 0.821460 -0.120784 0.210230 0.205 Uiso 1 1 calc R U . . .
O4 O 0.9246(6) -0.0075(5) -0.00342(10) 0.0533(10) Uani 1 1 d . . . . .
C4 C 0.8916(13) 0.1089(17) 0.2632(2) 0.104(4) Uani 1 1 d . . . . .
H4A H 0.997745 0.070958 0.252336 0.156 Uiso 1 1 calc R U . . .
H4B H 0.876479 0.067648 0.288437 0.156 Uiso 1 1 calc R U . . .
H4C H 0.896719 0.217841 0.264656 0.156 Uiso 1 1 calc R U . . .
C5 C 0.7664(7) 0.2630(6) 0.19367(12) 0.0415(11) Uani 1 1 d . . . . .
C12 C 0.7585(8) 0.5743(6) 0.15686(13) 0.0469(12) Uani 1 1 d . . . . .
H7 H 0.779919 0.581082 0.183054 0.056 Uiso 1 1 calc R U . . .
N1 N 0.7699(6) 0.2909(5) 0.15472(10) 0.0367(9) Uani 1 1 d . . . . .
C7 C 0.7130(7) 0.2644(5) 0.08929(11) 0.0361(10) Uani 1 1 d . . . . .
C8 C 0.7209(7) 0.4244(5) 0.10067(12) 0.0384(10) Uani 1 1 d . . . . .
C17 C 0.7218(7) 0.0803(5) 0.04054(11) 0.0370(10) Uani 1 1 d . . . . .
C14 C 0.8266(6) 0.2050(6) 0.05653(12) 0.0375(10) Uani 1 1 d . . . . .
C13 C 0.7516(7) 0.4361(5) 0.13895(12) 0.0379(10) Uani 1 1 d . . . . .
C9 C 0.6836(8) 0.5501(7) 0.08002(14) 0.0480(12) Uani 1 1 d . . . . .
H25 H 0.653396 0.542437 0.054265 0.058 Uiso 1 1 calc R U . . .
C25 C 0.3859(8) 0.0434(9) 0.12570(15) 0.0574(15) Uani 1 1 d . . . . .
H20 H 0.441152 -0.039520 0.114462 0.069 Uiso 1 1 calc R U . . .
C28 C 0.6743(14) -0.1848(11) -0.06179(19) 0.085(3) Uani 1 1 d . . . . .
H2 H 0.731698 -0.090896 -0.067865 0.128 Uiso 1 1 calc R U . . .
H15 H 0.551035 -0.168427 -0.060783 0.128 Uiso 1 1 calc R U . . .
H16 H 0.700306 -0.258936 -0.081157 0.128 Uiso 1 1 calc R U . . .
C16 C 0.9014(8) 0.3135(7) 0.02741(13) 0.0510(13) Uani 1 1 d . . . . .
H10 H 0.875405 0.284992 0.001173 0.061 Uiso 1 1 calc R U . . .
H11 H 0.869286 0.418561 0.032027 0.061 Uiso 1 1 calc R U . . .
C15 C 1.0144(7) 0.1738(8) 0.06636(13) 0.0488(13) Uani 1 1 d . . . . .
H8 H 1.044714 0.202306 0.092374 0.059 Uiso 1 1 calc R U . . .
H9 H 1.049696 0.070052 0.061112 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6910(9) 0.6893(7) 0.09764(15) 0.0541(14) Uani 1 1 d . . . . .
H26 H 0.667051 0.776886 0.083627 0.065 Uiso 1 1 calc R U . . .
C26 C 0.7881(7) -0.0229(6) 0.01176(12) 0.0392(10) Uani 1 1 d . . . . .
C11 C 0.7333(10) 0.7008(6) 0.13559(15) 0.0541(14) Uani 1 1 d . . . . .
H27 H 0.744902 0.796189 0.146827 0.065 Uiso 1 1 calc R U . . .
C27 C 0.7349(9) -0.2395(7) -0.02477(16) 0.0576(15) Uani 1 1 d . . . . .
H14 H 0.686917 -0.339535 -0.019740 0.069 Uiso 1 1 calc R U . . .
H17 H 0.860607 -0.247715 -0.024925 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5598(6) 0.0834(5) 0.05287(11) 0.0351(9) Uani 1 1 d . . . . .
H18 H 0.476191 0.011514 0.046317 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5269(6) 0.2136(6) 0.07811(12) 0.0372(10) Uani 1 1 d . . . . .
H19 H 0.474354 0.294665 0.062722 0.045 Uiso 1 1 calc R U . . .
C23 C 0.1991(10) 0.1435(15) 0.1730(2) 0.088(3) Uani 1 1 d . . . . .
H24 H 0.125258 0.128891 0.193776 0.106 Uiso 1 1 calc R U . . .
C20 C 0.4115(7) 0.1844(7) 0.11171(12) 0.0459(12) Uani 1 1 d . . . . .
C24 C 0.2777(12) 0.0223(15) 0.15665(19) 0.090(3) Uani 1 1 d . . . . .
H21 H 0.258784 -0.074967 0.166298 0.108 Uiso 1 1 calc R U . . .
C21 C 0.3288(8) 0.3057(10) 0.12863(18) 0.0630(18) Uani 1 1 d . . . . .
H22 H 0.343401 0.403305 0.118849 0.076 Uiso 1 1 calc R U . . .
C22 C 0.2256(10) 0.2823(15) 0.1598(2) 0.085(3) Uani 1 1 d . . . . .
H23 H 0.173310 0.364752 0.171866 0.101 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 C5 1.291(6) . ?
O1 C2 1.477(5) . ?
C1 C2 1.483(12) . ?
C1 H1 0.9793 . ?
C1 H5 0.9803 . ?
C1 H6 0.9820 . ?
C1 H35 1.0057 . ?
O6 C16 1.442(9) . ?
O6 C15 1.457(7) . ?
O5 C6 1.212(6) . ?
C6 N1 1.412(6) . ?
C6 C7 1.529(6) . ?
O2 C5 1.175(7) . ?
C2 C4 1.485(10) . ?
C2 C3 1.493(10) . ?
O3 C26 1.339(7) . ?
O3 C27 1.466(6) . ?
C3 H3 0.9800 . ?
C3 H29 0.9800 . ?
C3 H30 0.9800 . ?
O4 C26 1.208(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.410(5) . ?
C12 C11 1.379(8) . ?
C12 C13 1.396(7) . ?
C12 H7 0.9500 . ?
N1 C13 1.427(6) . ?
C7 C8 1.494(6) . ?
C7 C14 1.562(6) . ?
C7 C19 1.582(7) . ?
C8 C9 1.379(7) . ?
C8 C13 1.389(6) . ?
C17 C18 1.346(7) . ?
C17 C26 1.477(6) . ?
C17 C14 1.502(7) . ?
C14 C16 1.539(7) . ?
C14 C15 1.542(7) . ?
C9 C10 1.400(9) . ?
C9 H25 0.9500 . ?
C25 C20 1.376(10) . ?
C25 C24 1.404(8) . ?
C25 H20 0.9500 . ?
C28 C27 1.485(10) . ?
C28 H2 0.9800 . ?
C28 H15 0.9800 . ?
C28 H16 0.9800 . ?
C16 H10 0.9900 . ?
C16 H11 0.9900 . ?
C15 H8 0.9900 . ?
C15 H9 0.9900 . ?
C10 C11 1.396(7) . ?
C10 H26 0.9500 . ?
C11 H27 0.9500 . ?
C27 H14 0.9900 . ?
C27 H17 0.9900 . ?
C18 C19 1.497(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.524(6) . ?
C19 H19 1.0000 . ?
C23 C22 1.348(17) . ?
C23 C24 1.379(17) . ?
C23 H24 0.9500 . ?
C20 C21 1.403(9) . ?
C24 H21 0.9500 . ?
C21 C22 1.390(12) . ?
C21 H22 0.9500 . ?
C22 H23 0.9500 . ?

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 O1 C2 121.4(4) . . ?
C2 C1 H1 111.5 . . ?
C2 C1 H5 110.5 . . ?
H1 C1 H5 109.5 . . ?
C2 C1 H6 106.3 . . ?
H1 C1 H6 109.7 . . ?
H5 C1 H6 109.3 . . ?
C2 C1 H35 115.1 . . ?
H1 C1 H35 64.4 . . ?
H5 C1 H35 132.7 . . ?
H6 C1 H35 46.1 . . ?
C16 O6 C15 91.1(4) . . ?
O5 C6 N1 126.1(4) . . ?
O5 C6 C7 125.6(4) . . ?
N1 C6 C7 108.3(4) . . ?
O1 C2 C1 111.1(6) . . ?
O1 C2 C4 111.6(5) . . ?
C1 C2 C4 112.4(8) . . ?
O1 C2 C3 100.9(4) . . ?
C1 C2 C3 109.9(11) . . ?
C4 C2 C3 110.3(10) . . ?
C26 O3 C27 115.8(4) . . ?
C2 C3 H3 109.5 . . ?
C2 C3 H29 109.5 . . ?
H3 C3 H29 109.5 . . ?
C2 C3 H30 109.5 . . ?
H3 C3 H30 109.5 . . ?
H29 C3 H30 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 O1 126.4(4) . . ?
O2 C5 N1 122.5(5) . . ?
O1 C5 N1 111.1(4) . . ?
C11 C12 C13 118.4(4) . . ?
C11 C12 H7 120.8 . . ?
C13 C12 H7 120.8 . . ?
C5 N1 C6 127.1(4) . . ?
C5 N1 C13 123.2(4) . . ?
C6 N1 C13 109.0(3) . . ?
C8 C7 C6 102.2(3) . . ?
C8 C7 C14 120.5(4) . . ?
C6 C7 C14 109.0(4) . . ?
C8 C7 C19 112.5(4) . . ?
C6 C7 C19 108.3(4) . . ?
C14 C7 C19 104.0(3) . . ?
C9 C8 C13 119.9(4) . . ?
C9 C8 C7 129.3(4) . . ?
C13 C8 C7 110.3(4) . . ?
C18 C17 C26 124.9(4) . . ?
C18 C17 C14 112.2(4) . . ?
C26 C17 C14 122.6(4) . . ?
C17 C14 C16 115.2(4) . . ?
C17 C14 C15 118.4(5) . . ?
C16 C14 C15 84.4(4) . . ?
C17 C14 C7 103.0(4) . . ?
C16 C14 C7 120.4(4) . . ?
C15 C14 C7 116.0(4) . . ?
C8 C13 C12 121.5(4) . . ?
C8 C13 N1 109.6(4) . . ?
C12 C13 N1 128.9(4) . . ?
C8 C9 C10 118.9(4) . . ?
C8 C9 H25 120.6 . . ?
C10 C9 H25 120.6 . . ?
C20 C25 C24 119.8(8) . . ?
C20 C25 H20 120.1 . . ?
C24 C25 H20 120.1 . . ?
C27 C28 H2 109.5 . . ?
C27 C28 H15 109.5 . . ?
H2 C28 H15 109.5 . . ?
C27 C28 H16 109.5 . . ?
H2 C28 H16 109.5 . . ?
H15 C28 H16 109.5 . . ?
O6 C16 C14 92.6(4) . . ?
O6 C16 H10 113.2 . . ?
C14 C16 H10 113.2 . . ?
O6 C16 H11 113.2 . . ?
C14 C16 H11 113.2 . . ?
H10 C16 H11 110.5 . . ?
O6 C15 C14 91.9(4) . . ?
O6 C15 H8 113.3 . . ?
C14 C15 H8 113.3 . . ?
O6 C15 H9 113.3 . . ?
C14 C15 H9 113.3 . . ?
H8 C15 H9 110.6 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H26 119.7 . . ?
C9 C10 H26 119.7 . . ?
O4 C26 O3 124.0(4) . . ?
O4 C26 C17 123.5(5) . . ?
O3 C26 C17 112.6(4) . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H27 119.8 . . ?
C10 C11 H27 119.8 . . ?
O3 C27 C28 109.3(6) . . ?
O3 C27 H14 109.8 . . ?
C28 C27 H14 109.8 . . ?
O3 C27 H17 109.8 . . ?
C28 C27 H17 109.8 . . ?
H14 C27 H17 108.3 . . ?
C17 C18 C19 112.0(4) . . ?
C17 C18 H18 124.0 . . ?
C19 C18 H18 124.0 . . ?
C18 C19 C20 116.1(4) . . ?
C18 C19 C7 102.5(4) . . ?
C20 C19 C7 113.7(4) . . ?
C18 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C7 C19 H19 108.1 . . ?
C22 C23 C24 120.9(7) . . ?
C22 C23 H24 119.6 . . ?
C24 C23 H24 119.6 . . ?
C25 C20 C21 119.4(6) . . ?
C25 C20 C19 122.0(5) . . ?
C21 C20 C19 118.6(6) . . ?
C23 C24 C25 119.7(10) . . ?
C23 C24 H21 120.2 . . ?
C25 C24 H21 120.2 . . ?
C22 C21 C20 119.7(8) . . ?
C22 C21 H22 120.2 . . ?
C20 C21 H22 120.2 . . ?
C23 C22 C21 120.5(8) . . ?
C23 C22 H23 119.7 . . ?
C21 C22 H23 119.7 . . ?

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
C5 O1 C2 C1 63.5(9) . . . . ?
C5 O1 C2 C4 -62.8(10) . . . . ?
C5 O1 C2 C3 180.0(10) . . . . ?
C2 O1 C5 O2 5.8(11) . . . . ?
C2 O1 C5 N1 -175.0(5) . . . . ?
O2 C5 N1 C6 -177.6(7) . . . . ?
O1 C5 N1 C6 3.1(8) . . . . ?
O2 C5 N1 C13 -8.9(10) . . . . ?
O1 C5 N1 C13 171.8(5) . . . . ?
O5 C6 N1 C5 -19.0(8) . . . . ?
C7 C6 N1 C5 162.0(5) . . . . ?
O5 C6 N1 C13 171.0(5) . . . . ?
C7 C6 N1 C13 -8.0(6) . . . . ?
O5 C6 C7 C8 -170.6(5) . . . . ?
N1 C6 C7 C8 8.4(5) . . . . ?
O5 C6 C7 C14 -42.1(7) . . . . ?
N1 C6 C7 C14 136.9(4) . . . . ?
O5 C6 C7 C19 70.4(6) . . . . ?
N1 C6 C7 C19 -110.6(4) . . . . ?
C6 C7 C8 C9 -177.8(6) . . . . ?
C14 C7 C8 C9 61.4(8) . . . . ?
C19 C7 C8 C9 -61.8(7) . . . . ?
C6 C7 C8 C13 -5.9(6) . . . . ?
C14 C7 C8 C13 -126.8(5) . . . . ?
C19 C7 C8 C13 110.0(5) . . . . ?
C18 C17 C14 C16 -119.0(5) . . . . ?
C26 C17 C14 C16 55.3(7) . . . . ?
C18 C17 C14 C15 143.4(4) . . . . ?
C26 C17 C14 C15 -42.2(6) . . . . ?
C18 C17 C14 C7 14.0(5) . . . . ?
C26 C17 C14 C7 -171.7(4) . . . . ?
C8 C7 C14 C17 -150.2(4) . . . . ?
C6 C7 C14 C17 92.4(4) . . . . ?
C19 C7 C14 C17 -23.0(5) . . . . ?
C8 C7 C14 C16 -20.3(7) . . . . ?
C6 C7 C14 C16 -137.8(5) . . . . ?
C19 C7 C14 C16 106.9(5) . . . . ?
C8 C7 C14 C15 78.9(6) . . . . ?
C6 C7 C14 C15 -38.5(6) . . . . ?
C19 C7 C14 C15 -153.9(4) . . . . ?
C9 C8 C13 C12 -4.9(9) . . . . ?
C7 C8 C13 C12 -177.6(5) . . . . ?
C9 C8 C13 N1 174.2(5) . . . . ?
C7 C8 C13 N1 1.5(6) . . . . ?
C11 C12 C13 C8 0.2(10) . . . . ?
C11 C12 C13 N1 -178.7(6) . . . . ?
C5 N1 C13 C8 -166.3(5) . . . . ?
C6 N1 C13 C8 4.2(6) . . . . ?
C5 N1 C13 C12 12.7(9) . . . . ?
C6 N1 C13 C12 -176.8(6) . . . . ?
C13 C8 C9 C10 5.1(9) . . . . ?
C7 C8 C9 C10 176.3(6) . . . . ?
C15 O6 C16 C14 0.5(4) . . . . ?
C17 C14 C16 O6 -119.3(5) . . . . ?
C15 C14 C16 O6 -0.5(4) . . . . ?
C7 C14 C16 O6 116.5(5) . . . . ?
C16 O6 C15 C14 -0.5(4) . . . . ?
C17 C14 C15 O6 116.1(5) . . . . ?
C16 C14 C15 O6 0.5(4) . . . . ?
C7 C14 C15 O6 -120.7(5) . . . . ?
C8 C9 C10 C11 -0.8(10) . . . . ?
C27 O3 C26 O4 -2.8(8) . . . . ?
C27 O3 C26 C17 177.6(4) . . . . ?
C18 C17 C26 O4 166.9(5) . . . . ?
C14 C17 C26 O4 -6.7(7) . . . . ?
C18 C17 C26 O3 -13.6(7) . . . . ?
C14 C17 C26 O3 172.8(4) . . . . ?
C13 C12 C11 C10 4.2(11) . . . . ?
C9 C10 C11 C12 -3.9(11) . . . . ?
C26 O3 C27 C28 -88.4(8) . . . . ?
C26 C17 C18 C19 -172.2(4) . . . . ?
C14 C17 C18 C19 2.0(5) . . . . ?
C17 C18 C19 C20 -141.3(4) . . . . ?
C17 C18 C19 C7 -16.8(5) . . . . ?
C8 C7 C19 C18 156.0(3) . . . . ?
C6 C7 C19 C18 -91.8(4) . . . . ?
C14 C7 C19 C18 24.0(5) . . . . ?
C8 C7 C19 C20 -77.9(5) . . . . ?
C6 C7 C19 C20 34.3(6) . . . . ?
C14 C7 C19 C20 150.1(4) . . . . ?
C24 C25 C20 C21 0.0(9) . . . . ?
C24 C25 C20 C19 -179.8(6) . . . . ?
C18 C19 C20 C25 21.5(7) . . . . ?
C7 C19 C20 C25 -97.1(6) . . . . ?
C18 C19 C20 C21 -158.3(5) . . . . ?
C7 C19 C20 C21 83.1(6) . . . . ?
C22 C23 C24 C25 -0.5(13) . . . . ?
C20 C25 C24 C23 -0.5(12) . . . . ?
C25 C20 C21 C22 1.5(9) . . . . ?
C19 C20 C21 C22 -178.7(5) . . . . ?
C24 C23 C22 C21 2.0(13) . . . . ?
C20 C21 C22 C23 -2.5(11) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.084



####################################################################### 
# 
# 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_cu_220627_hj3_121a1_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2361587'
loop_
_audit_author_name
_audit_author_address
'Weijun Yao'
;Zhejiang SciTech University
China
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 N O6'
_chemical_formula_weight         475.52

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.9244(3)
_cell_length_b                   10.4924(3)
_cell_length_c                   13.3388(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.9920(10)
_cell_angle_gamma                90
_cell_volume                     1248.84(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9458
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      68.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19964
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.314
_diffrn_reflns_theta_max         68.317
_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 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4516
_reflns_number_gt                4497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.973

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 2061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4516
_refine_ls_number_parameters     320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.34851(16) 0.70425(13) 0.85581(9) 0.0390(3) Uani 1 1 d . . . . .
O2 O 0.18269(13) 0.27111(15) 0.30517(9) 0.0385(3) Uani 1 1 d . . . . .
O3 O -0.00728(15) 0.39153(15) 0.35762(10) 0.0445(4) Uani 1 1 d . . . . .
O4 O 0.38900(15) 0.63663(13) 0.66936(9) 0.0379(3) Uani 1 1 d . . . . .
O5 O 0.22586(19) 0.56942(16) 0.95673(10) 0.0503(4) Uani 1 1 d . . . . .
N1 N 0.27174(15) 0.51646(14) 0.79351(10) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.2206(3) 0.8548(2) 0.96703(18) 0.0522(5) Uani 1 1 d . . . . .
H1 H 0.161281 0.883882 0.908925 0.078 Uiso 1 1 calc R U . . .
H8 H 0.236509 0.925990 1.013549 0.078 Uiso 1 1 calc R U . . .
H9 H 0.167018 0.786171 1.001034 0.078 Uiso 1 1 calc R U . . .
C2 C 0.3713(2) 0.80557(18) 0.93225(14) 0.0380(4) Uani 1 1 d . . . . .
C3 C 0.27913(18) 0.59784(17) 0.87769(12) 0.0298(3) Uani 1 1 d . . . . .
C4 C 0.32151(16) 0.54330(17) 0.69508(11) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.27934(16) 0.43026(16) 0.62826(10) 0.0248(3) Uani 1 1 d . . . . .
C6 C 0.16087(16) 0.46162(16) 0.54258(11) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.20913(17) 0.36948(16) 0.46193(11) 0.0256(3) Uani 1 1 d . . . . .
O7 O -0.01171(17) 0.60358(16) 0.54795(13) 0.0531(4) Uani 1 1 d . . . . .
C8 C 0.11456(18) 0.34597(17) 0.37107(12) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.0942(3) 0.2414(2) 0.21634(15) 0.0519(6) Uani 1 1 d . . . . .
H29 H 0.088790 0.316688 0.171651 0.062 Uiso 1 1 calc R U . . .
H30 H -0.009037 0.218106 0.235257 0.062 Uiso 1 1 calc R U . . .
C10 C 0.1653(3) 0.1341(3) 0.16412(17) 0.0596(6) Uani 1 1 d . . . . .
H27 H 0.270365 0.154817 0.151385 0.089 Uiso 1 1 calc R U . . .
H28 H 0.112522 0.118523 0.100262 0.089 Uiso 1 1 calc R U . . .
H2 H 0.160414 0.057492 0.205998 0.089 Uiso 1 1 calc R U . . .
C11 C 0.4684(2) 0.7556(2) 1.01818(16) 0.0484(5) Uani 1 1 d . . . . .
H31 H 0.415060 0.687427 1.052883 0.073 Uiso 1 1 calc R U . . .
H4 H 0.490389 0.825062 1.065313 0.073 Uiso 1 1 calc R U . . .
H3 H 0.562327 0.722165 0.991802 0.073 Uiso 1 1 calc R U . . .
C12 C 0.4529(4) 0.9056(2) 0.8722(2) 0.0625(7) Uani 1 1 d . . . . .
H5 H 0.546507 0.869604 0.847264 0.094 Uiso 1 1 calc R U . . .
H7 H 0.475466 0.979189 0.915035 0.094 Uiso 1 1 calc R U . . .
H6 H 0.389484 0.932582 0.815338 0.094 Uiso 1 1 calc R U . . .
C13 C 0.21116(16) 0.39046(16) 0.79664(11) 0.0247(3) Uani 1 1 d . . . . .
C14 C 0.21646(15) 0.33595(16) 0.70157(11) 0.0245(3) Uani 1 1 d . . . . .
C15 C 0.16234(16) 0.21355(16) 0.68595(11) 0.0263(3) Uani 1 1 d . . . . .
H13 H 0.161842 0.176958 0.620797 0.032 Uiso 1 1 calc R U . . .
C16 C 0.10872(16) 0.14508(17) 0.76730(12) 0.0292(3) Uani 1 1 d . . . . .
H10 H 0.074362 0.060125 0.758046 0.035 Uiso 1 1 calc R U . . .
C17 C 0.10521(18) 0.20021(19) 0.86171(12) 0.0311(3) Uani 1 1 d . . . . .
H12 H 0.068048 0.152281 0.916356 0.037 Uiso 1 1 calc R U . . .
C18 C 0.15501(18) 0.32429(17) 0.87807(12) 0.0292(3) Uani 1 1 d . . . . .
H11 H 0.150777 0.362391 0.942570 0.035 Uiso 1 1 calc R U . . .
C19 C 0.13795(19) 0.60154(19) 0.50817(13) 0.0350(4) Uani 1 1 d . . . . .
H15 H 0.207182 0.662289 0.541837 0.042 Uiso 1 1 calc R U . . .
H14 H 0.140172 0.612318 0.434479 0.042 Uiso 1 1 calc R U . . .
C20 C -0.00341(17) 0.4718(2) 0.57564(13) 0.0352(4) Uani 1 1 d . . . . .
H16 H -0.072614 0.416912 0.536066 0.042 Uiso 1 1 calc R U . . .
H17 H -0.016093 0.457239 0.648331 0.042 Uiso 1 1 calc R U . . .
C21 C 0.34806(17) 0.32714(17) 0.47645(11) 0.0273(3) Uani 1 1 d . . . . .
H26 H 0.396506 0.268757 0.433282 0.033 Uiso 1 1 calc R U . . .
C22 C 0.41940(16) 0.38291(16) 0.56962(11) 0.0258(3) Uani 1 1 d . . . . .
H25 H 0.476915 0.460073 0.548936 0.031 Uiso 1 1 calc R U . . .
C23 C 0.52558(16) 0.29855(18) 0.62912(12) 0.0278(3) Uani 1 1 d . . . . .
C24 C 0.64007(18) 0.3548(2) 0.68637(13) 0.0336(4) Uani 1 1 d . . . . .
H20 H 0.653115 0.444603 0.685318 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7355(2) 0.2789(2) 0.74522(14) 0.0418(4) Uani 1 1 d . . . . .
H24 H 0.814494 0.317297 0.783110 0.050 Uiso 1 1 calc R U . . .
C26 C 0.7157(2) 0.1495(2) 0.74859(13) 0.0412(4) Uani 1 1 d . . . . .
H21 H 0.778326 0.098656 0.790770 0.049 Uiso 1 1 calc R U . . .
C27 C 0.60401(19) 0.0927(2) 0.69033(14) 0.0384(4) Uani 1 1 d . . . . .
H22 H 0.592026 0.002782 0.691201 0.046 Uiso 1 1 calc R U . . .
C28 C 0.50982(17) 0.16721(19) 0.63080(13) 0.0320(4) Uani 1 1 d . . . . .
H23 H 0.433837 0.127797 0.590837 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.312(2) . ?
O1 C2 1.485(2) . ?
O2 C8 1.333(2) . ?
O2 C9 1.4465(19) . ?
O3 C8 1.199(2) . ?
O4 C4 1.203(2) . ?
O5 C3 1.202(2) . ?
N1 C3 1.411(2) . ?
N1 C4 1.4215(19) . ?
N1 C13 1.429(2) . ?
C1 C2 1.520(3) . ?
C1 H1 0.9800 . ?
C1 H8 0.9800 . ?
C1 H9 0.9800 . ?
C2 C12 1.514(3) . ?
C2 C11 1.518(3) . ?
C4 C5 1.527(2) . ?
C5 C14 1.506(2) . ?
C5 C22 1.567(2) . ?
C5 C6 1.5781(19) . ?
C6 C7 1.514(2) . ?
C6 C20 1.5419(19) . ?
C6 C19 1.551(2) . ?
C7 C21 1.328(2) . ?
C7 C8 1.4854(19) . ?
O7 C20 1.433(3) . ?
O7 C19 1.446(2) . ?
C9 C10 1.474(4) . ?
C9 H29 0.9900 . ?
C9 H30 0.9900 . ?
C10 H27 0.9800 . ?
C10 H28 0.9800 . ?
C10 H2 0.9800 . ?
C11 H31 0.9800 . ?
C11 H4 0.9800 . ?
C11 H3 0.9800 . ?
C12 H5 0.9800 . ?
C12 H7 0.9800 . ?
C12 H6 0.9800 . ?
C13 C18 1.390(2) . ?
C13 C14 1.393(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.393(2) . ?
C15 H13 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H10 0.9500 . ?
C17 C18 1.392(3) . ?
C17 H12 0.9500 . ?
C18 H11 0.9500 . ?
C19 H15 0.9900 . ?
C19 H14 0.9900 . ?
C20 H16 0.9900 . ?
C20 H17 0.9900 . ?
C21 C22 1.5049(19) . ?
C21 H26 0.9500 . ?
C22 C23 1.512(2) . ?
C22 H25 1.0000 . ?
C23 C28 1.385(3) . ?
C23 C24 1.396(2) . ?
C24 C25 1.397(3) . ?
C24 H20 0.9500 . ?
C25 C26 1.371(4) . ?
C25 H24 0.9500 . ?
C26 C27 1.387(3) . ?
C26 H21 0.9500 . ?
C27 C28 1.387(3) . ?
C27 H22 0.9500 . ?
C28 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.07(13) . . ?
C8 O2 C9 114.71(15) . . ?
C3 N1 C4 127.15(15) . . ?
C3 N1 C13 123.30(13) . . ?
C4 N1 C13 109.55(13) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H8 109.5 . . ?
H1 C1 H8 109.5 . . ?
C2 C1 H9 109.5 . . ?
H1 C1 H9 109.5 . . ?
H8 C1 H9 109.5 . . ?
O1 C2 C12 101.19(15) . . ?
O1 C2 C11 109.94(16) . . ?
C12 C2 C11 111.4(2) . . ?
O1 C2 C1 109.97(16) . . ?
C12 C2 C1 111.2(2) . . ?
C11 C2 C1 112.52(17) . . ?
O5 C3 O1 127.00(16) . . ?
O5 C3 N1 122.29(16) . . ?
O1 C3 N1 110.71(13) . . ?
O4 C4 N1 126.22(16) . . ?
O4 C4 C5 125.84(13) . . ?
N1 C4 C5 107.91(14) . . ?
C14 C5 C4 102.83(11) . . ?
C14 C5 C22 115.16(13) . . ?
C4 C5 C22 110.30(12) . . ?
C14 C5 C6 110.77(11) . . ?
C4 C5 C6 114.59(13) . . ?
C22 C5 C6 103.58(11) . . ?
C7 C6 C20 122.06(14) . . ?
C7 C6 C19 115.58(14) . . ?
C20 C6 C19 84.15(13) . . ?
C7 C6 C5 100.73(12) . . ?
C20 C6 C5 115.83(12) . . ?
C19 C6 C5 119.67(13) . . ?
C21 C7 C8 125.40(14) . . ?
C21 C7 C6 112.72(13) . . ?
C8 C7 C6 121.40(14) . . ?
C20 O7 C19 92.08(13) . . ?
O3 C8 O2 124.00(15) . . ?
O3 C8 C7 123.86(16) . . ?
O2 C8 C7 112.12(14) . . ?
O2 C9 C10 108.54(18) . . ?
O2 C9 H29 110.0 . . ?
C10 C9 H29 110.0 . . ?
O2 C9 H30 110.0 . . ?
C10 C9 H30 110.0 . . ?
H29 C9 H30 108.4 . . ?
C9 C10 H27 109.5 . . ?
C9 C10 H28 109.5 . . ?
H27 C10 H28 109.5 . . ?
C9 C10 H2 109.5 . . ?
H27 C10 H2 109.5 . . ?
H28 C10 H2 109.5 . . ?
C2 C11 H31 109.5 . . ?
C2 C11 H4 109.5 . . ?
H31 C11 H4 109.5 . . ?
C2 C11 H3 109.5 . . ?
H31 C11 H3 109.5 . . ?
H4 C11 H3 109.5 . . ?
C2 C12 H5 109.5 . . ?
C2 C12 H7 109.5 . . ?
H5 C12 H7 109.5 . . ?
C2 C12 H6 109.5 . . ?
H5 C12 H6 109.5 . . ?
H7 C12 H6 109.5 . . ?
C18 C13 C14 121.66(15) . . ?
C18 C13 N1 128.79(14) . . ?
C14 C13 N1 109.54(14) . . ?
C15 C14 C13 120.00(15) . . ?
C15 C14 C5 130.05(14) . . ?
C13 C14 C5 109.89(14) . . ?
C14 C15 C16 118.95(14) . . ?
C14 C15 H13 120.5 . . ?
C16 C15 H13 120.5 . . ?
C17 C16 C15 120.38(16) . . ?
C17 C16 H10 119.8 . . ?
C15 C16 H10 119.8 . . ?
C16 C17 C18 121.36(15) . . ?
C16 C17 H12 119.3 . . ?
C18 C17 H12 119.3 . . ?
C13 C18 C17 117.59(15) . . ?
C13 C18 H11 121.2 . . ?
C17 C18 H11 121.2 . . ?
O7 C19 C6 91.34(13) . . ?
O7 C19 H15 113.4 . . ?
C6 C19 H15 113.4 . . ?
O7 C19 H14 113.4 . . ?
C6 C19 H14 113.4 . . ?
H15 C19 H14 110.7 . . ?
O7 C20 C6 92.19(14) . . ?
O7 C20 H16 113.3 . . ?
C6 C20 H16 113.3 . . ?
O7 C20 H17 113.3 . . ?
C6 C20 H17 113.3 . . ?
H16 C20 H17 110.6 . . ?
C7 C21 C22 111.78(14) . . ?
C7 C21 H26 124.1 . . ?
C22 C21 H26 124.1 . . ?
C21 C22 C23 117.28(15) . . ?
C21 C22 C5 101.87(11) . . ?
C23 C22 C5 114.95(12) . . ?
C21 C22 H25 107.4 . . ?
C23 C22 H25 107.4 . . ?
C5 C22 H25 107.4 . . ?
C28 C23 C24 119.01(17) . . ?
C28 C23 C22 121.87(15) . . ?
C24 C23 C22 119.09(17) . . ?
C23 C24 C25 120.01(19) . . ?
C23 C24 H20 120.0 . . ?
C25 C24 H20 120.0 . . ?
C26 C25 C24 120.35(19) . . ?
C26 C25 H24 119.8 . . ?
C24 C25 H24 119.8 . . ?
C25 C26 C27 119.91(18) . . ?
C25 C26 H21 120.0 . . ?
C27 C26 H21 120.0 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H22 120.0 . . ?
C28 C27 H22 120.0 . . ?
C23 C28 C27 120.59(18) . . ?
C23 C28 H23 119.7 . . ?
C27 C28 H23 119.7 . . ?

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
C3 O1 C2 C12 -179.65(19) . . . . ?
C3 O1 C2 C11 62.5(2) . . . . ?
C3 O1 C2 C1 -62.0(2) . . . . ?
C2 O1 C3 O5 1.0(3) . . . . ?
C2 O1 C3 N1 -179.74(14) . . . . ?
C4 N1 C3 O5 175.46(17) . . . . ?
C13 N1 C3 O5 -4.9(3) . . . . ?
C4 N1 C3 O1 -3.8(2) . . . . ?
C13 N1 C3 O1 175.82(14) . . . . ?
C3 N1 C4 O4 6.2(3) . . . . ?
C13 N1 C4 O4 -173.44(15) . . . . ?
C3 N1 C4 C5 -175.84(14) . . . . ?
C13 N1 C4 C5 4.47(16) . . . . ?
O4 C4 C5 C14 172.67(16) . . . . ?
N1 C4 C5 C14 -5.25(15) . . . . ?
O4 C4 C5 C22 49.4(2) . . . . ?
N1 C4 C5 C22 -128.56(13) . . . . ?
O4 C4 C5 C6 -67.0(2) . . . . ?
N1 C4 C5 C6 115.03(14) . . . . ?
C14 C5 C6 C7 -95.60(14) . . . . ?
C4 C5 C6 C7 148.63(12) . . . . ?
C22 C5 C6 C7 28.42(15) . . . . ?
C14 C5 C6 C20 38.19(19) . . . . ?
C4 C5 C6 C20 -77.59(18) . . . . ?
C22 C5 C6 C20 162.21(15) . . . . ?
C14 C5 C6 C19 136.55(15) . . . . ?
C4 C5 C6 C19 20.77(19) . . . . ?
C22 C5 C6 C19 -99.43(16) . . . . ?
C20 C6 C7 C21 -148.46(16) . . . . ?
C19 C6 C7 C21 111.96(16) . . . . ?
C5 C6 C7 C21 -18.53(18) . . . . ?
C20 C6 C7 C8 39.1(2) . . . . ?
C19 C6 C7 C8 -60.5(2) . . . . ?
C5 C6 C7 C8 169.04(14) . . . . ?
C9 O2 C8 O3 -3.5(3) . . . . ?
C9 O2 C8 C7 178.15(16) . . . . ?
C21 C7 C8 O3 -175.52(19) . . . . ?
C6 C7 C8 O3 -4.1(3) . . . . ?
C21 C7 C8 O2 2.8(3) . . . . ?
C6 C7 C8 O2 174.24(15) . . . . ?
C8 O2 C9 C10 -165.5(2) . . . . ?
C3 N1 C13 C18 -2.1(2) . . . . ?
C4 N1 C13 C18 177.56(15) . . . . ?
C3 N1 C13 C14 178.59(13) . . . . ?
C4 N1 C13 C14 -1.70(16) . . . . ?
C18 C13 C14 C15 1.2(2) . . . . ?
N1 C13 C14 C15 -179.48(13) . . . . ?
C18 C13 C14 C5 178.83(14) . . . . ?
N1 C13 C14 C5 -1.85(16) . . . . ?
C4 C5 C14 C15 -178.36(14) . . . . ?
C22 C5 C14 C15 -58.4(2) . . . . ?
C6 C5 C14 C15 58.8(2) . . . . ?
C4 C5 C14 C13 4.32(15) . . . . ?
C22 C5 C14 C13 124.33(13) . . . . ?
C6 C5 C14 C13 -118.56(13) . . . . ?
C13 C14 C15 C16 -2.5(2) . . . . ?
C5 C14 C15 C16 -179.62(14) . . . . ?
C14 C15 C16 C17 2.0(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
N1 C13 C18 C17 -178.52(14) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C20 O7 C19 C6 -3.88(14) . . . . ?
C7 C6 C19 O7 126.47(14) . . . . ?
C20 C6 C19 O7 3.62(13) . . . . ?
C5 C6 C19 O7 -112.85(15) . . . . ?
C19 O7 C20 C6 3.90(14) . . . . ?
C7 C6 C20 O7 -120.26(17) . . . . ?
C19 C6 C20 O7 -3.65(13) . . . . ?
C5 C6 C20 O7 116.56(15) . . . . ?
C8 C7 C21 C22 172.05(15) . . . . ?
C6 C7 C21 C22 0.0(2) . . . . ?
C7 C21 C22 C23 145.17(15) . . . . ?
C7 C21 C22 C5 18.78(18) . . . . ?
C14 C5 C22 C21 92.34(14) . . . . ?
C4 C5 C22 C21 -151.85(13) . . . . ?
C6 C5 C22 C21 -28.76(16) . . . . ?
C14 C5 C22 C23 -35.56(18) . . . . ?
C4 C5 C22 C23 80.25(17) . . . . ?
C6 C5 C22 C23 -156.67(14) . . . . ?
C21 C22 C23 C28 -29.5(2) . . . . ?
C5 C22 C23 C28 90.19(19) . . . . ?
C21 C22 C23 C24 152.44(14) . . . . ?
C5 C22 C23 C24 -87.88(18) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C22 C23 C24 C25 177.30(15) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C24 C25 C26 C27 2.5(3) . . . . ?
C25 C26 C27 C28 -1.8(3) . . . . ?
C24 C23 C28 C27 1.5(3) . . . . ?
C22 C23 C28 C27 -176.51(14) . . . . ?
C26 C27 C28 C23 -0.3(3) . . . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033




