# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2181908'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2022-06-26 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Br2 N O4'
_chemical_formula_sum            'C24 H19 Br2 N O4'
_chemical_formula_weight         545.22
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9588(12)
_cell_length_b                   14.9466(14)
_cell_length_c                   12.5105(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.475(5)
_cell_angle_gamma                90
_cell_volume                     2094.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7172
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.359
_shelx_estimated_absorpt_T_min   0.326
_exptl_absorpt_coefficient_mu    3.902
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1394 before and 0.0901 after correction.
The Ratio of minimum to maximum transmission is 0.6157.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28620
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3177
_reflns_number_total             5157
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+3.6603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1188
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C17(H17), C21(H21), C22(H22), C24(H24)
;
_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 0.12431(5) 0.40950(4) 0.48756(4) 0.05014(16) Uani 1 1 d . . . . .
Br2 Br 0.59719(4) 0.99610(3) 0.36405(4) 0.04105(15) Uani 1 1 d . . . . .
O1 O 0.3170(3) 0.53772(17) 0.1310(2) 0.0292(6) Uani 1 1 d . . . . .
O2 O 0.2499(3) 0.27418(18) 0.1368(3) 0.0399(7) Uani 1 1 d . . . . .
O3 O 0.5446(3) 0.60767(17) 0.4608(2) 0.0281(6) Uani 1 1 d . . . . .
O4 O 0.5494(3) 0.67165(17) 0.1452(2) 0.0332(7) Uani 1 1 d . . . . .
N1 N 0.5519(3) 0.39894(19) 0.2408(3) 0.0241(7) Uani 1 1 d . . . . .
C1 C 0.1853(4) 0.4485(3) 0.3745(4) 0.0333(10) Uani 1 1 d . . . . .
C2 C 0.2024(4) 0.5388(3) 0.3632(4) 0.0356(10) Uani 1 1 d . . . . .
H2 H 0.183097 0.580727 0.411149 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2476(4) 0.5679(3) 0.2819(4) 0.0324(9) Uani 1 1 d . . . . .
H3 H 0.258674 0.629976 0.272777 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2768(4) 0.5056(3) 0.2134(3) 0.0272(8) Uani 1 1 d . . . . .
C5 C 0.2597(4) 0.4148(3) 0.2244(3) 0.0274(9) Uani 1 1 d . . . . .
C6 C 0.2125(4) 0.3862(3) 0.3068(3) 0.0298(9) Uani 1 1 d . . . . .
H6 H 0.199519 0.324345 0.315585 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2891(4) 0.3501(3) 0.1493(3) 0.0270(9) Uani 1 1 d . . . . .
C8 C 0.3711(4) 0.3811(2) 0.0881(3) 0.0263(9) Uani 1 1 d . . . . .
H8 H 0.336463 0.365041 0.005439 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4000(4) 0.4824(2) 0.1015(3) 0.0266(9) Uani 1 1 d . . . . .
H9 H 0.403301 0.504610 0.027219 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5285(4) 0.4886(2) 0.1917(3) 0.0238(8) Uani 1 1 d . . . . .
H10 H 0.585338 0.500503 0.150844 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6797(4) 0.3807(3) 0.2962(4) 0.0321(9) Uani 1 1 d . . . . .
H11A H 0.713677 0.421377 0.362049 0.039 Uiso 1 1 calc R U . . .
H11B H 0.721346 0.391819 0.241610 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6988(4) 0.2844(3) 0.3366(4) 0.0359(10) Uani 1 1 d . . . . .
H12A H 0.662333 0.274475 0.395470 0.043 Uiso 1 1 calc R U . . .
H12B H 0.785384 0.272047 0.371259 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6429(4) 0.2210(3) 0.2368(4) 0.0394(11) Uani 1 1 d . . . . .
H13A H 0.651390 0.158541 0.264996 0.047 Uiso 1 1 calc R U . . .
H13B H 0.685375 0.226310 0.181901 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5109(4) 0.2423(3) 0.1764(4) 0.0331(10) Uani 1 1 d . . . . .
H14A H 0.477866 0.204019 0.107978 0.040 Uiso 1 1 calc R U . . .
H14B H 0.466275 0.229782 0.228140 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4968(4) 0.3401(2) 0.1417(3) 0.0273(9) Uani 1 1 d . . . . .
H15 H 0.539970 0.349786 0.087075 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5417(3) 0.5615(2) 0.2771(3) 0.0232(8) Uani 1 1 d . . . . .
C17 C 0.5392(4) 0.5447(3) 0.3810(3) 0.0265(9) Uani 1 1 d . . . . .
H17 H 0.533199 0.483897 0.400620 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5551(3) 0.6953(2) 0.4337(3) 0.0250(8) Uani 1 1 d . . . . .
C19 C 0.5583(3) 0.7209(2) 0.3282(3) 0.0242(8) Uani 1 1 d . . . . .
C20 C 0.5501(4) 0.6531(3) 0.2409(3) 0.0258(8) Uani 1 1 d . . . . .
C21 C 0.5627(4) 0.7583(3) 0.5180(3) 0.0331(10) Uani 1 1 d . . . . .
H21 H 0.559231 0.739879 0.589404 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5752(4) 0.8470(3) 0.4970(4) 0.0348(10) Uani 1 1 d . . . . .
H22 H 0.581368 0.890526 0.554171 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5790(4) 0.8730(3) 0.3917(3) 0.0291(9) Uani 1 1 d . . . . .
C24 C 0.5709(4) 0.8117(2) 0.3075(3) 0.0279(9) Uani 1 1 d . . . . .
H24 H 0.573919 0.830783 0.236112 0.034 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 C1 1.896(4) . ?
Br2 C23 1.899(4) . ?
O1 C4 1.368(5) . ?
O1 C9 1.435(5) . ?
O2 C7 1.217(4) . ?
O3 C17 1.357(4) . ?
O3 C18 1.370(4) . ?
O4 C20 1.227(4) . ?
N1 C10 1.459(4) . ?
N1 C11 1.466(5) . ?
N1 C15 1.474(5) . ?
C1 C2 1.380(6) . ?
C1 C6 1.373(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.404(6) . ?
C5 C7 1.474(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.512(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.549(5) . ?
C8 C15 1.543(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.559(5) . ?
C10 H10 1.0000 . ?
C10 C16 1.495(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.516(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.518(5) . ?
C15 H15 1.0000 . ?
C16 C17 1.335(5) . ?
C16 C20 1.456(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 C21 1.392(5) . ?
C19 C20 1.468(5) . ?
C19 C24 1.401(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.370(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(6) . ?
C23 C24 1.373(5) . ?
C24 H24 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
C4 O1 C9 116.6(3) . . ?
C17 O3 C18 117.8(3) . . ?
C10 N1 C11 112.6(3) . . ?
C10 N1 C15 103.3(3) . . ?
C11 N1 C15 111.8(3) . . ?
C2 C1 Br1 119.1(3) . . ?
C6 C1 Br1 119.2(3) . . ?
C6 C1 C2 121.7(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 117.4(3) . . ?
O1 C4 C5 121.5(3) . . ?
C5 C4 C3 121.1(4) . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 C7 120.2(4) . . ?
C6 C5 C7 121.0(4) . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O2 C7 C5 121.8(4) . . ?
O2 C7 C8 120.7(4) . . ?
C5 C7 C8 117.6(3) . . ?
C7 C8 H8 110.0 . . ?
C7 C8 C9 113.9(3) . . ?
C7 C8 C15 111.4(3) . . ?
C9 C8 H8 110.0 . . ?
C15 C8 H8 110.0 . . ?
C15 C8 C9 101.3(3) . . ?
O1 C9 C8 116.3(3) . . ?
O1 C9 H9 107.7 . . ?
O1 C9 C10 112.0(3) . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C10 105.1(3) . . ?
C10 C9 H9 107.7 . . ?
N1 C10 C9 104.2(3) . . ?
N1 C10 H10 108.3 . . ?
N1 C10 C16 114.4(3) . . ?
C9 C10 H10 108.3 . . ?
C16 C10 C9 113.0(3) . . ?
C16 C10 H10 108.3 . . ?
N1 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
N1 C11 C12 110.2(3) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C11 C12 C13 110.2(3) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 C14 110.9(3) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 C13 109.6(3) . . ?
C15 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
N1 C15 C8 102.0(3) . . ?
N1 C15 C14 111.2(3) . . ?
N1 C15 H15 107.6 . . ?
C8 C15 H15 107.6 . . ?
C14 C15 C8 120.0(3) . . ?
C14 C15 H15 107.6 . . ?
C17 C16 C10 121.7(3) . . ?
C17 C16 C20 120.5(3) . . ?
C20 C16 C10 117.7(3) . . ?
O3 C17 H17 117.5 . . ?
C16 C17 O3 125.0(3) . . ?
C16 C17 H17 117.5 . . ?
O3 C18 C19 122.3(3) . . ?
O3 C18 C21 116.5(3) . . ?
C19 C18 C21 121.2(4) . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 C24 118.9(3) . . ?
C24 C19 C20 121.0(3) . . ?
O4 C20 C16 122.6(3) . . ?
O4 C20 C19 123.1(3) . . ?
C16 C20 C19 114.3(3) . . ?
C18 C21 H21 120.3 . . ?
C22 C21 C18 119.5(4) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(4) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 Br2 119.1(3) . . ?
C24 C23 Br2 119.2(3) . . ?
C24 C23 C22 121.7(4) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 C19 119.2(4) . . ?
C23 C24 H24 120.4 . . ?

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
C3 H3 O2 0.95 2.45 3.243(5) 140.6 2 yes
C12 H12B O4 0.99 2.55 3.387(5) 142.8 2_645 yes
C14 H14B O2 0.99 2.52 3.022(5) 110.9 . yes
C17 H17 O3 0.95 2.62 3.390(5) 138.3 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 179.5(3) . . . . ?
Br1 C1 C6 C5 -178.9(3) . . . . ?
Br2 C23 C24 C19 179.6(3) . . . . ?
O1 C4 C5 C6 -176.8(4) . . . . ?
O1 C4 C5 C7 2.3(6) . . . . ?
O1 C9 C10 N1 114.8(3) . . . . ?
O1 C9 C10 C16 -10.0(4) . . . . ?
O2 C7 C8 C9 172.8(4) . . . . ?
O2 C7 C8 C15 -73.5(5) . . . . ?
O3 C18 C19 C20 0.2(6) . . . . ?
O3 C18 C19 C24 -179.1(3) . . . . ?
O3 C18 C21 C22 179.0(4) . . . . ?
N1 C10 C16 C17 -19.0(6) . . . . ?
N1 C10 C16 C20 164.7(3) . . . . ?
N1 C11 C12 C13 57.2(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C3 C4 O1 177.5(4) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C3 C4 C5 C7 178.8(4) . . . . ?
C4 O1 C9 C8 43.2(4) . . . . ?
C4 O1 C9 C10 -77.7(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C4 C5 C7 O2 -162.0(4) . . . . ?
C4 C5 C7 C8 18.4(6) . . . . ?
C5 C7 C8 C9 -7.7(5) . . . . ?
C5 C7 C8 C15 106.1(4) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C6 C5 C7 O2 17.0(6) . . . . ?
C6 C5 C7 C8 -162.5(4) . . . . ?
C7 C5 C6 C1 -179.5(4) . . . . ?
C7 C8 C9 O1 -21.7(5) . . . . ?
C7 C8 C9 C10 102.8(4) . . . . ?
C7 C8 C15 N1 -81.1(3) . . . . ?
C7 C8 C15 C14 42.3(5) . . . . ?
C8 C9 C10 N1 -12.4(4) . . . . ?
C8 C9 C10 C16 -137.2(3) . . . . ?
C9 O1 C4 C3 149.4(4) . . . . ?
C9 O1 C4 C5 -33.9(5) . . . . ?
C9 C8 C15 N1 40.3(3) . . . . ?
C9 C8 C15 C14 163.7(3) . . . . ?
C9 C10 C16 C17 100.1(4) . . . . ?
C9 C10 C16 C20 -76.2(4) . . . . ?
C10 N1 C11 C12 -175.2(3) . . . . ?
C10 N1 C15 C8 -50.1(3) . . . . ?
C10 N1 C15 C14 -179.3(3) . . . . ?
C10 C16 C17 O3 -176.5(4) . . . . ?
C10 C16 C20 O4 -1.7(6) . . . . ?
C10 C16 C20 C19 177.8(3) . . . . ?
C11 N1 C10 C9 159.3(3) . . . . ?
C11 N1 C10 C16 -76.8(4) . . . . ?
C11 N1 C15 C8 -171.5(3) . . . . ?
C11 N1 C15 C14 59.3(4) . . . . ?
C11 C12 C13 C14 -55.5(5) . . . . ?
C12 C13 C14 C15 54.5(4) . . . . ?
C13 C14 C15 N1 -55.9(4) . . . . ?
C13 C14 C15 C8 -174.8(3) . . . . ?
C15 N1 C10 C9 38.5(3) . . . . ?
C15 N1 C10 C16 162.4(3) . . . . ?
C15 N1 C11 C12 -59.4(4) . . . . ?
C15 C8 C9 O1 -141.4(3) . . . . ?
C15 C8 C9 C10 -16.9(4) . . . . ?
C17 O3 C18 C19 1.0(5) . . . . ?
C17 O3 C18 C21 -178.8(4) . . . . ?
C17 C16 C20 O4 -178.0(4) . . . . ?
C17 C16 C20 C19 1.5(6) . . . . ?
C18 O3 C17 C16 -1.0(6) . . . . ?
C18 C19 C20 O4 178.1(4) . . . . ?
C18 C19 C20 C16 -1.4(5) . . . . ?
C18 C19 C24 C23 -0.4(6) . . . . ?
C18 C21 C22 C23 0.6(6) . . . . ?
C19 C18 C21 C22 -0.9(6) . . . . ?
C20 C16 C17 O3 -0.3(6) . . . . ?
C20 C19 C24 C23 -179.7(4) . . . . ?
C21 C18 C19 C20 -180.0(4) . . . . ?
C21 C18 C19 C24 0.7(6) . . . . ?
C21 C22 C23 Br2 -179.7(3) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C23 C24 C19 0.2(6) . . . . ?
C24 C19 C20 O4 -2.7(6) . . . . ?
C24 C19 C20 C16 177.9(4) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2182166'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N O4'
_chemical_formula_weight         455.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           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                   6.8138(6)
_cell_length_b                   10.4409(11)
_cell_length_c                   16.4586(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.287(4)
_cell_angle_gamma                90
_cell_volume                     1169.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3109
_cell_measurement_theta_min      2.4790
_cell_measurement_theta_max      28.0853

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            10047
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5490
_reflns_number_gt                3291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.944

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0517P)²+0.0271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.055(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5490
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.6958(4) 0.3376(3) 0.70893(18) 0.0550(8) Uani 1 1 d . . . . .
O2 O 0.2332(4) 0.7980(3) 0.81060(19) 0.0622(9) Uani 1 1 d . . . . .
O3 O 0.1784(4) 0.5318(3) 0.70328(19) 0.0599(9) Uani 1 1 d . . . . .
O4 O 0.7933(4) 0.6627(3) 0.81109(17) 0.0554(8) Uani 1 1 d . . . . .
N1 N 0.6975(4) 0.7065(3) 0.62053(18) 0.0429(8) Uani 1 1 d . . . . .
C1 C 0.4114(8) 0.1095(5) 0.8158(3) 0.0688(14) Uani 1 1 d . . . . .
H1 H 0.4290 0.0287 0.8389 0.083 Uiso 1 1 calc R U . . .
C2 C 0.5637(7) 0.1633(5) 0.7769(3) 0.0640(13) Uani 1 1 d . . . . .
H22 H 0.6817 0.1197 0.7727 0.077 Uiso 1 1 calc R U . . .
C3 C 0.5366(6) 0.2848(4) 0.7439(3) 0.0482(10) Uani 1 1 d . . . . .
C4 C 0.6798(6) 0.4601(4) 0.6832(2) 0.0476(10) Uani 1 1 d . . . . .
H21 H 0.7908 0.4973 0.6628 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5182(5) 0.5324(4) 0.6846(2) 0.0395(9) Uani 1 1 d . . . . .
C6 C 0.5192(5) 0.6715(4) 0.6603(2) 0.0429(9) Uani 1 1 d . . . . .
H20 H 0.4049 0.6885 0.6229 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5183(6) 0.7686(4) 0.7336(2) 0.0459(10) Uani 1 1 d . . . . .
H7 H 0.4831 0.8532 0.7115 0.055 Uiso 1 1 calc R U . . .
C8 C 0.3877(6) 0.7413(4) 0.8025(2) 0.0463(10) Uani 1 1 d . . . . .
C9 C 0.4636(6) 0.6438(4) 0.8599(2) 0.0462(10) Uani 1 1 d . . . . .
C10 C 0.3419(7) 0.5790(4) 0.9114(3) 0.0523(11) Uani 1 1 d . . . . .
H4 H 0.2116 0.6047 0.9134 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4087(7) 0.4778(5) 0.9597(3) 0.0565(12) Uani 1 1 d . . . . .
C12 C 0.2746(8) 0.4054(6) 1.0120(3) 0.0806(17) Uani 1 1 d . . . . .
H5 H 0.1423 0.4354 1.0018 0.121 Uiso 1 1 calc R U . . .
H2 H 0.3146 0.4187 1.0683 0.121 Uiso 1 1 calc R U . . .
H6 H 0.2809 0.3157 0.9995 0.121 Uiso 1 1 calc R U . . .
C13 C 0.6051(7) 0.4433(5) 0.9560(3) 0.0644(13) Uani 1 1 d . . . . .
H3 H 0.6530 0.3753 0.9878 0.077 Uiso 1 1 calc R U . . .
C14 C 0.7311(7) 0.5058(5) 0.9073(3) 0.0616(13) Uani 1 1 d . . . . .
H29 H 0.8620 0.4807 0.9066 0.074 Uiso 1 1 calc R U . . .
C15 C 0.6608(6) 0.6073(5) 0.8589(2) 0.0498(11) Uani 1 1 d . . . . .
C16 C 0.7337(6) 0.7714(5) 0.7613(2) 0.0496(11) Uani 1 1 d . . . . .
H28 H 0.7662 0.8516 0.7899 0.059 Uiso 1 1 calc R U . . .
C17 C 0.8414(6) 0.7631(4) 0.6826(2) 0.0458(10) Uani 1 1 d . . . . .
H27 H 0.9565 0.7071 0.6905 0.055 Uiso 1 1 calc R U . . .
C18 C 0.6684(6) 0.7983(4) 0.5528(2) 0.0484(10) Uani 1 1 d . . . . .
H19 H 0.5645 0.8586 0.5658 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8621(6) 0.8699(5) 0.5545(3) 0.0544(11) Uani 1 1 d . . . . .
H18 H 0.8454 0.9522 0.5263 0.065 Uiso 1 1 calc R U . . .
C20 C 1.0229(6) 0.7915(5) 0.5171(3) 0.0590(12) Uani 1 1 d . . . . .
H14 H 1.1379 0.8451 0.5121 0.071 Uiso 1 1 calc R U . . .
H15 H 1.0600 0.7211 0.5532 0.071 Uiso 1 1 calc R U . . .
C21 C 0.9582(7) 0.7384(6) 0.4338(3) 0.0673(14) Uani 1 1 d . . . . .
H12 H 0.9313 0.8085 0.3961 0.081 Uiso 1 1 calc R U . . .
H13 H 1.0627 0.6867 0.4133 0.081 Uiso 1 1 calc R U . . .
C22 C 0.7758(7) 0.6578(5) 0.4397(3) 0.0658(13) Uani 1 1 d . . . . .
H8 H 0.8056 0.5850 0.4750 0.079 Uiso 1 1 calc R U . . .
H11 H 0.7350 0.6252 0.3862 0.079 Uiso 1 1 calc R U . . .
C23 C 0.6095(6) 0.7336(5) 0.4729(2) 0.0577(12) Uani 1 1 d . . . . .
H10 H 0.4996 0.6767 0.4806 0.069 Uiso 1 1 calc R U . . .
H9 H 0.5663 0.7981 0.4334 0.069 Uiso 1 1 calc R U . . .
C24 C 0.9015(7) 0.8914(5) 0.6462(3) 0.0621(13) Uani 1 1 d . . . . .
H16 H 1.0392 0.9098 0.6594 0.074 Uiso 1 1 calc R U . . .
H17 H 0.8223 0.9611 0.6655 0.074 Uiso 1 1 calc R U . . .
C25 C 0.3589(5) 0.3477(4) 0.7470(2) 0.0413(9) Uani 1 1 d . . . . .
C26 C 0.3377(5) 0.4758(4) 0.7109(2) 0.0415(9) Uani 1 1 d . . . . .
C27 C 0.2082(6) 0.2893(5) 0.7862(3) 0.0519(11) Uani 1 1 d . . . . .
H26 H 0.0881 0.3311 0.7886 0.062 Uiso 1 1 calc R U . . .
C28 C 0.2330(7) 0.1701(5) 0.8220(3) 0.0579(12) Uani 1 1 d . . . . .
C29 C 0.0738(9) 0.1084(6) 0.8686(4) 0.0866(18) Uani 1 1 d . . . . .
H25 H -0.0284 0.1696 0.8766 0.130 Uiso 1 1 calc R U . . .
H24 H 0.1283 0.0796 0.9205 0.130 Uiso 1 1 calc R U . . .
H23 H 0.0202 0.0366 0.8384 0.130 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 C4 1.349(5) . ?
O1 C3 1.372(5) . ?
O2 C8 1.221(5) . ?
O3 C26 1.233(4) . ?
O4 C15 1.360(5) . ?
O4 C16 1.445(5) . ?
N1 C6 1.459(5) . ?
N1 C18 1.475(5) . ?
N1 C17 1.497(5) . ?
C1 C2 1.371(7) . ?
C1 C28 1.380(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(6) . ?
C2 H22 0.9300 . ?
C3 C25 1.381(5) . ?
C4 C5 1.337(5) . ?
C4 H21 0.9300 . ?
C5 C26 1.453(5) . ?
C5 C6 1.506(6) . ?
C6 C7 1.576(6) . ?
C6 H20 0.9800 . ?
C7 C8 1.509(6) . ?
C7 C16 1.512(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.463(6) . ?
C9 C10 1.394(6) . ?
C9 C15 1.398(5) . ?
C10 C11 1.384(6) . ?
C10 H4 0.9300 . ?
C11 C13 1.391(6) . ?
C11 C12 1.496(7) . ?
C12 H5 0.9600 . ?
C12 H2 0.9600 . ?
C12 H6 0.9600 . ?
C13 C14 1.372(6) . ?
C13 H3 0.9300 . ?
C14 C15 1.394(6) . ?
C14 H29 0.9300 . ?
C16 C17 1.526(5) . ?
C16 H28 0.9800 . ?
C17 C24 1.533(6) . ?
C17 H27 0.9800 . ?
C18 C23 1.512(6) . ?
C18 C19 1.516(6) . ?
C18 H19 0.9800 . ?
C19 C20 1.526(6) . ?
C19 C24 1.535(6) . ?
C19 H18 0.9800 . ?
C20 C21 1.521(7) . ?
C20 H14 0.9700 . ?
C20 H15 0.9700 . ?
C21 C22 1.509(7) . ?
C21 H12 0.9700 . ?
C21 H13 0.9700 . ?
C22 C23 1.510(6) . ?
C22 H8 0.9700 . ?
C22 H11 0.9700 . ?
C23 H10 0.9700 . ?
C23 H9 0.9700 . ?
C24 H16 0.9700 . ?
C24 H17 0.9700 . ?
C25 C27 1.385(5) . ?
C25 C26 1.467(6) . ?
C27 C28 1.383(7) . ?
C27 H26 0.9300 . ?
C28 C29 1.509(7) . ?
C29 H25 0.9600 . ?
C29 H24 0.9600 . ?
C29 H23 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
C4 O1 C3 117.4(3) . . ?
C15 O4 C16 119.2(3) . . ?
C6 N1 C18 115.0(3) . . ?
C6 N1 C17 108.8(3) . . ?
C18 N1 C17 108.3(3) . . ?
C2 C1 C28 122.7(5) . . ?
C2 C1 H1 118.6 . . ?
C28 C1 H1 118.6 . . ?
C1 C2 C3 118.1(5) . . ?
C1 C2 H22 121.0 . . ?
C3 C2 H22 121.0 . . ?
O1 C3 C25 122.7(4) . . ?
O1 C3 C2 116.2(4) . . ?
C25 C3 C2 121.2(4) . . ?
C5 C4 O1 125.6(4) . . ?
C5 C4 H21 117.2 . . ?
O1 C4 H21 117.2 . . ?
C4 C5 C26 119.1(4) . . ?
C4 C5 C6 121.6(4) . . ?
C26 C5 C6 119.2(3) . . ?
N1 C6 C5 112.2(3) . . ?
N1 C6 C7 102.8(3) . . ?
C5 C6 C7 114.6(3) . . ?
N1 C6 H20 109.0 . . ?
C5 C6 H20 109.0 . . ?
C7 C6 H20 109.0 . . ?
C8 C7 C16 112.4(3) . . ?
C8 C7 C6 118.9(3) . . ?
C16 C7 C6 101.3(3) . . ?
C8 C7 H7 107.9 . . ?
C16 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
O2 C8 C9 122.8(4) . . ?
O2 C8 C7 122.7(4) . . ?
C9 C8 C7 114.5(4) . . ?
C10 C9 C15 118.7(4) . . ?
C10 C9 C8 122.0(4) . . ?
C15 C9 C8 119.1(4) . . ?
C11 C10 C9 122.2(4) . . ?
C11 C10 H4 118.9 . . ?
C9 C10 H4 118.9 . . ?
C10 C11 C13 117.3(4) . . ?
C10 C11 C12 121.7(4) . . ?
C13 C11 C12 121.0(5) . . ?
C11 C12 H5 109.5 . . ?
C11 C12 H2 109.5 . . ?
H5 C12 H2 109.5 . . ?
C11 C12 H6 109.5 . . ?
H5 C12 H6 109.5 . . ?
H2 C12 H6 109.5 . . ?
C14 C13 C11 122.6(5) . . ?
C14 C13 H3 118.7 . . ?
C11 C13 H3 118.7 . . ?
C13 C14 C15 119.3(4) . . ?
C13 C14 H29 120.4 . . ?
C15 C14 H29 120.4 . . ?
O4 C15 C14 115.9(4) . . ?
O4 C15 C9 124.1(4) . . ?
C14 C15 C9 120.0(4) . . ?
O4 C16 C7 113.1(3) . . ?
O4 C16 C17 107.7(3) . . ?
C7 C16 C17 104.4(3) . . ?
O4 C16 H28 110.5 . . ?
C7 C16 H28 110.5 . . ?
C17 C16 H28 110.5 . . ?
N1 C17 C16 105.9(3) . . ?
N1 C17 C24 104.9(3) . . ?
C16 C17 C24 115.7(4) . . ?
N1 C17 H27 110.0 . . ?
C16 C17 H27 110.0 . . ?
C24 C17 H27 110.0 . . ?
N1 C18 C23 112.6(4) . . ?
N1 C18 C19 103.1(3) . . ?
C23 C18 C19 115.1(3) . . ?
N1 C18 H19 108.6 . . ?
C23 C18 H19 108.6 . . ?
C19 C18 H19 108.6 . . ?
C18 C19 C20 111.9(4) . . ?
C18 C19 C24 101.2(3) . . ?
C20 C19 C24 112.7(4) . . ?
C18 C19 H18 110.2 . . ?
C20 C19 H18 110.2 . . ?
C24 C19 H18 110.2 . . ?
C21 C20 C19 112.4(3) . . ?
C21 C20 H14 109.1 . . ?
C19 C20 H14 109.1 . . ?
C21 C20 H15 109.1 . . ?
C19 C20 H15 109.1 . . ?
H14 C20 H15 107.9 . . ?
C22 C21 C20 110.0(4) . . ?
C22 C21 H12 109.7 . . ?
C20 C21 H12 109.7 . . ?
C22 C21 H13 109.7 . . ?
C20 C21 H13 109.7 . . ?
H12 C21 H13 108.2 . . ?
C21 C22 C23 111.6(5) . . ?
C21 C22 H8 109.3 . . ?
C23 C22 H8 109.3 . . ?
C21 C22 H11 109.3 . . ?
C23 C22 H11 109.3 . . ?
H8 C22 H11 108.0 . . ?
C22 C23 C18 112.4(3) . . ?
C22 C23 H10 109.1 . . ?
C18 C23 H10 109.1 . . ?
C22 C23 H9 109.1 . . ?
C18 C23 H9 109.1 . . ?
H10 C23 H9 107.9 . . ?
C17 C24 C19 102.8(4) . . ?
C17 C24 H16 111.2 . . ?
C19 C24 H16 111.2 . . ?
C17 C24 H17 111.2 . . ?
C19 C24 H17 111.2 . . ?
H16 C24 H17 109.1 . . ?
C3 C25 C27 118.9(4) . . ?
C3 C25 C26 119.0(4) . . ?
C27 C25 C26 122.1(4) . . ?
O3 C26 C5 122.1(4) . . ?
O3 C26 C25 122.6(4) . . ?
C5 C26 C25 115.3(3) . . ?
C28 C27 C25 121.3(4) . . ?
C28 C27 H26 119.4 . . ?
C25 C27 H26 119.4 . . ?
C1 C28 C27 117.9(5) . . ?
C1 C28 C29 120.3(5) . . ?
C27 C28 C29 121.8(5) . . ?
C28 C29 H25 109.5 . . ?
C28 C29 H24 109.5 . . ?
H25 C29 H24 109.5 . . ?
C28 C29 H23 109.5 . . ?
H25 C29 H23 109.5 . . ?
H24 C29 H23 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
C28 C1 C2 C3 1.1(8) . . . . ?
C4 O1 C3 C25 5.8(6) . . . . ?
C4 O1 C3 C2 -173.9(4) . . . . ?
C1 C2 C3 O1 177.0(4) . . . . ?
C1 C2 C3 C25 -2.7(7) . . . . ?
C3 O1 C4 C5 -4.1(6) . . . . ?
O1 C4 C5 C26 -4.0(6) . . . . ?
O1 C4 C5 C6 175.4(4) . . . . ?
C18 N1 C6 C5 142.4(3) . . . . ?
C17 N1 C6 C5 -95.9(4) . . . . ?
C18 N1 C6 C7 -94.0(4) . . . . ?
C17 N1 C6 C7 27.8(4) . . . . ?
C4 C5 C6 N1 12.0(5) . . . . ?
C26 C5 C6 N1 -168.6(3) . . . . ?
C4 C5 C6 C7 -104.8(4) . . . . ?
C26 C5 C6 C7 74.6(4) . . . . ?
N1 C6 C7 C8 -163.7(3) . . . . ?
C5 C6 C7 C8 -41.7(5) . . . . ?
N1 C6 C7 C16 -40.0(4) . . . . ?
C5 C6 C7 C16 82.0(4) . . . . ?
C16 C7 C8 O2 138.2(4) . . . . ?
C6 C7 C8 O2 -103.8(5) . . . . ?
C16 C7 C8 C9 -40.4(5) . . . . ?
C6 C7 C8 C9 77.7(4) . . . . ?
O2 C8 C9 C10 21.3(6) . . . . ?
C7 C8 C9 C10 -160.1(4) . . . . ?
O2 C8 C9 C15 -163.7(4) . . . . ?
C7 C8 C9 C15 14.8(5) . . . . ?
C15 C9 C10 C11 -1.8(6) . . . . ?
C8 C9 C10 C11 173.2(4) . . . . ?
C9 C10 C11 C13 0.9(7) . . . . ?
C9 C10 C11 C12 -177.4(4) . . . . ?
C10 C11 C13 C14 0.3(7) . . . . ?
C12 C11 C13 C14 178.5(5) . . . . ?
C11 C13 C14 C15 -0.5(8) . . . . ?
C16 O4 C15 C14 -177.9(4) . . . . ?
C16 O4 C15 C9 4.0(6) . . . . ?
C13 C14 C15 O4 -178.7(4) . . . . ?
C13 C14 C15 C9 -0.4(7) . . . . ?
C10 C9 C15 O4 179.6(4) . . . . ?
C8 C9 C15 O4 4.5(6) . . . . ?
C10 C9 C15 C14 1.5(6) . . . . ?
C8 C9 C15 C14 -173.6(4) . . . . ?
C15 O4 C16 C7 -30.7(5) . . . . ?
C15 O4 C16 C17 -145.5(4) . . . . ?
C8 C7 C16 O4 48.3(5) . . . . ?
C6 C7 C16 O4 -79.7(4) . . . . ?
C8 C7 C16 C17 165.0(3) . . . . ?
C6 C7 C16 C17 37.0(4) . . . . ?
C6 N1 C17 C16 -4.9(4) . . . . ?
C18 N1 C17 C16 120.8(4) . . . . ?
C6 N1 C17 C24 -127.7(4) . . . . ?
C18 N1 C17 C24 -2.0(4) . . . . ?
O4 C16 C17 N1 99.2(4) . . . . ?
C7 C16 C17 N1 -21.2(5) . . . . ?
O4 C16 C17 C24 -145.1(4) . . . . ?
C7 C16 C17 C24 94.4(4) . . . . ?
C6 N1 C18 C23 -85.1(4) . . . . ?
C17 N1 C18 C23 152.9(3) . . . . ?
C6 N1 C18 C19 150.2(3) . . . . ?
C17 N1 C18 C19 28.2(4) . . . . ?
N1 C18 C19 C20 77.4(4) . . . . ?
C23 C18 C19 C20 -45.6(5) . . . . ?
N1 C18 C19 C24 -42.8(4) . . . . ?
C23 C18 C19 C24 -165.8(4) . . . . ?
C18 C19 C20 C21 50.4(5) . . . . ?
C24 C19 C20 C21 163.7(4) . . . . ?
C19 C20 C21 C22 -57.2(6) . . . . ?
C20 C21 C22 C23 58.3(5) . . . . ?
C21 C22 C23 C18 -53.4(5) . . . . ?
N1 C18 C23 C22 -70.5(5) . . . . ?
C19 C18 C23 C22 47.3(5) . . . . ?
N1 C17 C24 C19 -24.6(4) . . . . ?
C16 C17 C24 C19 -140.8(3) . . . . ?
C18 C19 C24 C17 41.4(4) . . . . ?
C20 C19 C24 C17 -78.3(4) . . . . ?
O1 C3 C25 C27 -177.5(4) . . . . ?
C2 C3 C25 C27 2.2(6) . . . . ?
O1 C3 C25 C26 0.6(6) . . . . ?
C2 C3 C25 C26 -179.7(4) . . . . ?
C4 C5 C26 O3 -170.1(4) . . . . ?
C6 C5 C26 O3 10.5(6) . . . . ?
C4 C5 C26 C25 9.9(5) . . . . ?
C6 C5 C26 C25 -169.5(3) . . . . ?
C3 C25 C26 O3 171.8(4) . . . . ?
C27 C25 C26 O3 -10.2(6) . . . . ?
C3 C25 C26 C5 -8.2(5) . . . . ?
C27 C25 C26 C5 169.8(4) . . . . ?
C3 C25 C27 C28 0.0(6) . . . . ?
C26 C25 C27 C28 -178.0(4) . . . . ?
C2 C1 C28 C27 1.0(7) . . . . ?
C2 C1 C28 C29 -177.4(5) . . . . ?
C25 C27 C28 C1 -1.5(7) . . . . ?
C25 C27 C28 C29 176.9(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
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655
C17 H27 O3 0.98 2.38 3.336(5) 166.1 1_655

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044

