# 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. 
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data_cu_20170324mf_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1963637'
loop_
_audit_author_name
_audit_author_address
'jing linhai'
;china west normal university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_audit_creation_date             2018-03-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H25 F N2 O5'
_chemical_formula_sum            'C28 H25 F N2 O5'
_chemical_formula_weight         488.50
_chemical_absolute_configuration ad
_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 0.0181 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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.316(4)
_cell_length_b                   11.859(4)
_cell_length_c                   18.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2438.0(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8669
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      63.56
_cell_measurement_theta_min      3.90
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14025
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        63.780
_diffrn_reflns_theta_max         63.780
_diffrn_reflns_theta_min         4.452
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3656
_reflns_number_total             3990
_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 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 
;
 Flack x determined using 1447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1a), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C25(H25a,H25b,H25c)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.69205(18) 0.75432(16) 0.78038(10) 0.0476(5) Uani 1 1 d . . . . .
H1 H 0.6694 0.8195 0.7857 0.071 Uiso 1 1 calc GR . . . .
O2 O 0.45665(17) 0.44664(19) 0.68635(11) 0.0541(5) Uani 1 1 d . . . . .
O1AA O 0.48275(18) 0.6781(2) 0.60006(13) 0.0621(6) Uani 1 1 d . . . . .
O0AA O 0.8437(2) 0.91449(18) 0.73341(14) 0.0690(7) Uani 1 1 d . . . . .
O3 O 0.89193(19) 0.81373(18) 0.63401(14) 0.0612(6) Uani 1 1 d . . . . .
F4 F 1.0084(2) 0.2485(2) 0.65165(16) 0.1024(9) Uani 1 1 d . . . . .
N1 N 0.64538(19) 0.75167(19) 0.65360(11) 0.0392(5) Uani 1 1 d . . . . .
N2 N 0.5464(2) 0.3861(2) 0.57998(13) 0.0482(6) Uani 1 1 d . . . . .
C1 C 0.7013(7) 1.0276(7) 0.4417(5) 0.147(3) Uani 1 1 d . . . . .
H1A H 0.7228 1.0638 0.3983 0.176 Uiso 1 1 calc R . . . .
C2 C 0.7174(7) 1.0797(6) 0.5101(5) 0.138(3) Uani 1 1 d . . . . .
H2 H 0.7502 1.1515 0.5123 0.166 Uiso 1 1 calc R . . . .
C3 C 0.6856(4) 1.0264(4) 0.5733(3) 0.0911(13) Uani 1 1 d . . . . .
H3 H 0.6962 1.0621 0.6184 0.109 Uiso 1 1 calc R . . . .
C4 C 0.6376(3) 0.9197(3) 0.57074(17) 0.0511(7) Uani 1 1 d . . . . .
C5 C 0.5971(3) 0.8661(2) 0.64137(16) 0.0477(7) Uani 1 1 d . . . . .
H5A H 0.6203 0.9140 0.6822 0.057 Uiso 1 1 calc R . . . .
H5B H 0.5115 0.8619 0.6411 0.057 Uiso 1 1 calc R . . . .
C6 C 0.5769(2) 0.6635(2) 0.63055(14) 0.0407(6) Uani 1 1 d . . . . .
C7 C 0.6294(2) 0.5457(2) 0.63622(13) 0.0365(6) Uani 1 1 d . . . . .
C8 C 0.7071(2) 0.5307(2) 0.70586(13) 0.0350(5) Uani 1 1 d . . . . .
H8 H 0.6553 0.5410 0.7486 0.042 Uiso 1 1 calc R . . . .
C9 C 0.7597(2) 0.4140(2) 0.71183(13) 0.0365(6) Uani 1 1 d . . . . .
C10 C 0.7029(3) 0.3325(3) 0.75346(18) 0.0554(8) Uani 1 1 d . . . . .
H10 H 0.6330 0.3509 0.7775 0.066 Uiso 1 1 calc R . . . .
C11 C 0.7475(4) 0.2245(3) 0.7601(2) 0.0691(10) Uani 1 1 d . . . . .
H11 H 0.7070 0.1716 0.7882 0.083 Uiso 1 1 calc R . . . .
C12 C 0.8495(3) 0.1946(3) 0.7262(2) 0.0640(9) Uani 1 1 d . . . . .
H12 H 0.8801 0.1222 0.7303 0.077 Uiso 1 1 calc R . . . .
C13 C 0.7976(2) 0.6256(2) 0.70772(15) 0.0365(6) Uani 1 1 d . . . . .
H13A H 0.8472 0.6170 0.7509 0.044 Uiso 1 1 calc R . . . .
H13B H 0.8479 0.6204 0.6646 0.044 Uiso 1 1 calc R . . . .
C14 C 0.7390(2) 0.7410(2) 0.70944(14) 0.0388(6) Uani 1 1 d . . . . .
C15 C 0.8305(3) 0.8342(2) 0.69456(16) 0.0452(7) Uani 1 1 d . . . . .
C16 C 0.9793(4) 0.8969(3) 0.6124(3) 0.0889(14) Uani 1 1 d . . . . .
H16A H 1.0080 0.8796 0.5640 0.133 Uiso 1 1 calc GR . . . .
H16B H 1.0439 0.8956 0.6467 0.133 Uiso 1 1 calc GR . . . .
H16C H 0.9439 0.9704 0.6124 0.133 Uiso 1 1 calc GR . . . .
C17 C 0.9053(3) 0.2758(3) 0.68562(19) 0.0586(8) Uani 1 1 d . . . . .
C18 C 0.8641(3) 0.3838(2) 0.67728(16) 0.0475(7) Uani 1 1 d . . . . .
H18 H 0.9056 0.4358 0.6490 0.057 Uiso 1 1 calc R . . . .
C19 C 0.6893(2) 0.5198(2) 0.56327(14) 0.0395(6) Uani 1 1 d . . . . .
C20 C 0.7745(3) 0.5771(3) 0.52396(15) 0.0527(7) Uani 1 1 d . . . . .
H20 H 0.8077 0.6432 0.5422 0.063 Uiso 1 1 calc R . . . .
C21 C 0.8095(3) 0.5334(4) 0.45623(18) 0.0667(9) Uani 1 1 d . . . . .
H21 H 0.8677 0.5702 0.4292 0.080 Uiso 1 1 calc R . . . .
C22 C 0.7596(3) 0.4373(3) 0.42891(16) 0.0629(9) Uani 1 1 d . . . . .
H22 H 0.7853 0.4093 0.3838 0.076 Uiso 1 1 calc R . . . .
C23 C 0.6721(3) 0.3807(3) 0.46659(16) 0.0552(8) Uani 1 1 d . . . . .
H23 H 0.6377 0.3157 0.4477 0.066 Uiso 1 1 calc R . . . .
C24 C 0.6378(2) 0.4248(3) 0.53369(14) 0.0431(6) Uani 1 1 d . . . . .
C25 C 0.4810(4) 0.2824(3) 0.5686(3) 0.0786(11) Uani 1 1 d . . . . .
H25A H 0.4582 0.2768 0.5178 0.118 Uiso 1 1 calc GR . . . .
H25B H 0.4116 0.2826 0.5990 0.118 Uiso 1 1 calc GR . . . .
H25C H 0.5299 0.2192 0.5814 0.118 Uiso 1 1 calc GR . . . .
C26 C 0.5309(2) 0.4565(2) 0.63851(14) 0.0415(6) Uani 1 1 d . . . . .
C27 C 0.6208(5) 0.8709(4) 0.5042(2) 0.0913(14) Uani 1 1 d . . . . .
H27 H 0.5861 0.7999 0.5016 0.110 Uiso 1 1 calc R . . . .
C28 C 0.6539(7) 0.9241(6) 0.4406(3) 0.132(2) Uani 1 1 d . . . . .
H28 H 0.6433 0.8877 0.3957 0.158 Uiso 1 1 calc R . . . .


_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 H1 0.8200 . ?
O1 C14 1.403(3) . ?
O2 C26 1.214(3) . ?
O1AA C6 1.214(3) . ?
O0AA C15 1.194(3) . ?
O3 C15 1.324(4) . ?
O3 C16 1.450(4) . ?
F4 C17 1.360(4) . ?
N1 C5 1.479(3) . ?
N1 C6 1.366(4) . ?
N1 C14 1.472(3) . ?
N2 C24 1.411(4) . ?
N2 C25 1.449(4) . ?
N2 C26 1.364(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.398(11) . ?
C1 C28 1.340(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(6) . ?
C4 C5 1.504(4) . ?
C4 C27 1.354(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.522(4) . ?
C7 C8 1.551(3) . ?
C7 C19 1.520(4) . ?
C7 C26 1.538(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.511(4) . ?
C8 C13 1.522(3) . ?
C9 C10 1.386(4) . ?
C9 C18 1.385(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(6) . ?
C12 H12 0.9300 . ?
C12 C17 1.367(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.521(4) . ?
C14 C15 1.539(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 C24 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.366(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C27 H27 0.9300 . ?
C27 C28 1.369(6) . ?
C28 H28 0.9300 . ?

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
C14 O1 H1 109.5 . . ?
C15 O3 C16 117.2(3) . . ?
C6 N1 C5 116.5(2) . . ?
C6 N1 C14 123.6(2) . . ?
C14 N1 C5 116.6(2) . . ?
C24 N2 C25 124.4(3) . . ?
C26 N2 C24 111.1(2) . . ?
C26 N2 C25 124.4(3) . . ?
C2 C1 H1A 121.0 . . ?
C28 C1 H1A 121.0 . . ?
C28 C1 C2 118.1(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.7(3) . . ?
C27 C4 C3 118.5(4) . . ?
C27 C4 C5 122.6(3) . . ?
N1 C5 C4 113.8(2) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O1AA C6 N1 121.9(3) . . ?
O1AA C6 C7 120.3(3) . . ?
N1 C6 C7 117.4(2) . . ?
C6 C7 C8 112.4(2) . . ?
C6 C7 C26 110.5(2) . . ?
C19 C7 C6 107.5(2) . . ?
C19 C7 C8 115.8(2) . . ?
C19 C7 C26 102.0(2) . . ?
C26 C7 C8 108.0(2) . . ?
C7 C8 H8 107.0 . . ?
C9 C8 C7 112.8(2) . . ?
C9 C8 H8 107.0 . . ?
C9 C8 C13 114.2(2) . . ?
C13 C8 C7 108.3(2) . . ?
C13 C8 H8 107.0 . . ?
C10 C9 C8 119.7(2) . . ?
C18 C9 C8 122.8(2) . . ?
C18 C9 C10 117.5(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C17 117.0(3) . . ?
C17 C12 H12 121.5 . . ?
C8 C13 H13A 109.2 . . ?
C8 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C8 111.8(2) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
O1 C14 N1 110.5(2) . . ?
O1 C14 C13 106.6(2) . . ?
O1 C14 C15 109.6(2) . . ?
N1 C14 C13 112.2(2) . . ?
N1 C14 C15 107.5(2) . . ?
C13 C14 C15 110.5(2) . . ?
O0AA C15 O3 124.9(3) . . ?
O0AA C15 C14 123.6(3) . . ?
O3 C15 C14 111.5(2) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F4 C17 C12 118.3(3) . . ?
F4 C17 C18 117.6(3) . . ?
C12 C17 C18 124.1(3) . . ?
C9 C18 H18 120.6 . . ?
C17 C18 C9 118.7(3) . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C7 131.6(3) . . ?
C24 C19 C7 108.5(2) . . ?
C24 C19 C20 119.8(3) . . ?
C19 C20 H20 120.9 . . ?
C19 C20 C21 118.2(3) . . ?
C21 C20 H20 120.9 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.1(3) . . ?
C24 C23 H23 121.4 . . ?
C19 C24 N2 110.1(2) . . ?
C19 C24 C23 122.3(3) . . ?
C23 C24 N2 127.5(3) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 N2 126.0(2) . . ?
O2 C26 C7 126.0(2) . . ?
N2 C26 C7 107.9(2) . . ?
C4 C27 H27 119.4 . . ?
C4 C27 C28 121.2(5) . . ?
C28 C27 H27 119.4 . . ?
C1 C28 C27 121.2(6) . . ?
C1 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?

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
O1 C14 C15 O0AA -10.9(4) . . . . ?
O1 C14 C15 O3 168.9(2) . . . . ?
O1AA C6 C7 C8 -150.4(2) . . . . ?
O1AA C6 C7 C19 81.0(3) . . . . ?
O1AA C6 C7 C26 -29.6(3) . . . . ?
F4 C17 C18 C9 -179.5(3) . . . . ?
N1 C6 C7 C8 36.6(3) . . . . ?
N1 C6 C7 C19 -92.1(3) . . . . ?
N1 C6 C7 C26 157.4(2) . . . . ?
N1 C14 C15 O0AA 109.3(3) . . . . ?
N1 C14 C15 O3 -71.0(3) . . . . ?
C1 C2 C3 C4 0.4(10) . . . . ?
C2 C1 C28 C27 0.7(11) . . . . ?
C2 C3 C4 C5 -176.5(5) . . . . ?
C2 C3 C4 C27 -1.5(7) . . . . ?
C3 C4 C5 N1 -128.4(3) . . . . ?
C3 C4 C27 C28 2.1(8) . . . . ?
C4 C27 C28 C1 -1.8(10) . . . . ?
C5 N1 C6 O1AA 1.7(4) . . . . ?
C5 N1 C6 C7 174.6(2) . . . . ?
C5 N1 C14 O1 71.7(3) . . . . ?
C5 N1 C14 C13 -169.5(2) . . . . ?
C5 N1 C14 C15 -47.8(3) . . . . ?
C5 C4 C27 C28 177.0(5) . . . . ?
C6 N1 C5 C4 -93.8(3) . . . . ?
C6 N1 C14 O1 -87.0(3) . . . . ?
C6 N1 C14 C13 31.8(3) . . . . ?
C6 N1 C14 C15 153.4(2) . . . . ?
C6 C7 C8 C9 -179.9(2) . . . . ?
C6 C7 C8 C13 -52.5(3) . . . . ?
C6 C7 C19 C20 54.5(4) . . . . ?
C6 C7 C19 C24 -120.9(2) . . . . ?
C6 C7 C26 O2 -63.5(3) . . . . ?
C6 C7 C26 N2 120.5(2) . . . . ?
C7 C8 C9 C10 -95.1(3) . . . . ?
C7 C8 C9 C18 85.1(3) . . . . ?
C7 C8 C13 C14 59.2(3) . . . . ?
C7 C19 C20 C21 -177.7(3) . . . . ?
C7 C19 C24 N2 1.3(3) . . . . ?
C7 C19 C24 C23 179.0(3) . . . . ?
C8 C7 C19 C20 -72.2(4) . . . . ?
C8 C7 C19 C24 112.4(2) . . . . ?
C8 C7 C26 O2 60.0(3) . . . . ?
C8 C7 C26 N2 -116.1(2) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C8 C9 C18 C17 -179.8(3) . . . . ?
C8 C13 C14 O1 73.2(3) . . . . ?
C8 C13 C14 N1 -47.9(3) . . . . ?
C8 C13 C14 C15 -167.8(2) . . . . ?
C9 C8 C13 C14 -174.2(2) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C9 C18 C17 0.3(4) . . . . ?
C10 C11 C12 C17 0.0(6) . . . . ?
C11 C12 C17 F4 179.3(4) . . . . ?
C11 C12 C17 C18 -0.2(5) . . . . ?
C12 C17 C18 C9 0.1(5) . . . . ?
C13 C8 C9 C10 140.7(3) . . . . ?
C13 C8 C9 C18 -39.2(3) . . . . ?
C13 C14 C15 O0AA -128.0(3) . . . . ?
C13 C14 C15 O3 51.7(3) . . . . ?
C14 N1 C5 C4 105.9(3) . . . . ?
C14 N1 C6 O1AA 160.4(3) . . . . ?
C14 N1 C6 C7 -26.6(3) . . . . ?
C16 O3 C15 O0AA -1.9(5) . . . . ?
C16 O3 C15 C14 178.4(3) . . . . ?
C18 C9 C10 C11 -0.5(5) . . . . ?
C19 C7 C8 C9 -55.7(3) . . . . ?
C19 C7 C8 C13 71.7(3) . . . . ?
C19 C7 C26 O2 -177.5(3) . . . . ?
C19 C7 C26 N2 6.4(3) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C20 C19 C24 N2 -174.7(3) . . . . ?
C20 C19 C24 C23 3.0(4) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C22 C23 C24 N2 176.0(3) . . . . ?
C22 C23 C24 C19 -1.2(4) . . . . ?
C24 N2 C26 O2 177.8(3) . . . . ?
C24 N2 C26 C7 -6.1(3) . . . . ?
C24 C19 C20 C21 -2.8(5) . . . . ?
C25 N2 C24 C19 -174.3(3) . . . . ?
C25 N2 C24 C23 8.1(5) . . . . ?
C25 N2 C26 O2 -4.7(5) . . . . ?
C25 N2 C26 C7 171.3(3) . . . . ?
C26 N2 C24 C19 3.1(3) . . . . ?
C26 N2 C24 C23 -174.4(3) . . . . ?
C26 C7 C8 C9 57.9(3) . . . . ?
C26 C7 C8 C13 -174.7(2) . . . . ?
C26 C7 C19 C20 170.8(3) . . . . ?
C26 C7 C19 C24 -4.6(3) . . . . ?
C27 C4 C5 N1 56.7(5) . . . . ?
C28 C1 C2 C3 -0.1(11) . . . . ?

_shelx_SHELXL_version_number     2014/7

_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_20180303_sanxianan_0ma-auto
_database_code_depnum_ccdc_archive 'CCDC 1963639'
loop_
_audit_author_name
_audit_author_address
'jing linhai'
;china west normal university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_audit_creation_date             2018-03-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H16 N2 O2)'
_chemical_formula_sum            'C34 H32 N4 O4'
_chemical_formula_weight         560.63
_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 0.0181 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.2717(14)
_cell_length_b                   14.1714(9)
_cell_length_c                   9.3683(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.922(3)
_cell_angle_gamma                90
_cell_volume                     2935.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6352
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      59.78
_cell_measurement_theta_min      4.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37447
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        60.137
_diffrn_reflns_theta_max         60.137
_diffrn_reflns_theta_min         3.705
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             4369
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.6470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3A), C1(H1A), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C)
;
_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
O1 O 0.64913(8) 0.70958(11) 0.30413(15) 0.0651(5) Uani 1 1 d . . . . .
O2 O 0.79152(8) 0.74148(15) 0.3932(2) 0.0928(6) Uani 1 1 d . . . . .
O3 O 0.70158(8) 0.30090(13) 0.1968(2) 0.0805(5) Uani 1 1 d . . . . .
O4 O 0.83161(8) 0.21351(11) 0.23057(14) 0.0651(5) Uani 1 1 d . . . . .
N1 N 0.63581(8) 0.68314(12) 0.53519(18) 0.0547(5) Uani 1 1 d . . . . .
H1 H 0.6459 0.7002 0.6229 0.066 Uiso 1 1 calc R . . . .
N2 N 0.75603(10) 0.88750(16) 0.32141(19) 0.0684(6) Uani 1 1 d . . . . .
N3 N 0.84115(8) 0.18695(11) -0.00251(16) 0.0499(5) Uani 1 1 d . . . . .
H3A H 0.8292 0.2032 -0.0898 0.060 Uiso 1 1 calc R . . . .
N4 N 0.75611(8) 0.43856(13) 0.21402(19) 0.0565(5) Uani 1 1 d . . . . .
C1 C 0.41231(14) 0.6760(2) 0.5719(4) 0.0877(9) Uani 1 1 d . . . . .
H1A H 0.3727 0.6910 0.5848 0.105 Uiso 1 1 calc R . . . .
C2 C 0.43742(14) 0.7137(2) 0.4611(3) 0.0841(8) Uani 1 1 d . . . . .
H2 H 0.4150 0.7548 0.3981 0.101 Uiso 1 1 calc R . . . .
C3 C 0.49577(12) 0.69196(18) 0.4406(3) 0.0718(7) Uani 1 1 d . . . . .
H3 H 0.5125 0.7186 0.3637 0.086 Uiso 1 1 calc R . . . .
C4 C 0.53004(10) 0.63122(15) 0.5321(2) 0.0523(5) Uani 1 1 d . . . . .
C5 C 0.59344(10) 0.60520(16) 0.5071(3) 0.0639(6) Uani 1 1 d . . . . .
H5A H 0.6070 0.5526 0.5690 0.077 Uiso 1 1 calc R . . . .
H5B H 0.5933 0.5848 0.4083 0.077 Uiso 1 1 calc R . . . .
C6 C 0.65952(10) 0.72900(14) 0.4328(2) 0.0474(5) Uani 1 1 d . . . . .
C7 C 0.70194(10) 0.80967(14) 0.4822(2) 0.0478(5) Uani 1 1 d . . . . .
H7 H 0.7151 0.8052 0.5856 0.057 Uiso 1 1 calc R . . . .
C8 C 0.67490(10) 0.90421(15) 0.4447(2) 0.0539(6) Uani 1 1 d . . . . .
C9 C 0.70910(13) 0.94720(17) 0.3482(2) 0.0646(7) Uani 1 1 d . . . . .
C10 C 0.69474(19) 1.0365(2) 0.2951(3) 0.1020(12) Uani 1 1 d . . . . .
H10 H 0.7176 1.0660 0.2312 0.122 Uiso 1 1 calc R . . . .
C11 C 0.6448(2) 1.0801(3) 0.3415(5) 0.1253(18) Uani 1 1 d . . . . .
H11 H 0.6341 1.1401 0.3070 0.150 Uiso 1 1 calc R . . . .
C12 C 0.62546(13) 0.9484(2) 0.4890(3) 0.0830(8) Uani 1 1 d . . . . .
H12 H 0.6024 0.9191 0.5526 0.100 Uiso 1 1 calc R . . . .
C13 C 0.61092(19) 1.0386(3) 0.4356(5) 0.1172(14) Uani 1 1 d . . . . .
H13 H 0.5779 1.0705 0.4644 0.141 Uiso 1 1 calc R . . . .
C14 C 0.79970(15) 0.9083(3) 0.2217(3) 0.1188(14) Uani 1 1 d . . . . .
H14A H 0.8340 0.8672 0.2410 0.178 Uiso 1 1 calc GR . . . .
H14B H 0.8127 0.9727 0.2336 0.178 Uiso 1 1 calc GR . . . .
H14C H 0.7812 0.8988 0.1249 0.178 Uiso 1 1 calc GR . . . .
C15 C 0.75587(11) 0.80642(18) 0.3972(2) 0.0603(6) Uani 1 1 d . . . . .
C16 C 0.50445(13) 0.59272(18) 0.6453(3) 0.0705(7) Uani 1 1 d . . . . .
H16 H 0.5266 0.5514 0.7084 0.085 Uiso 1 1 calc R . . . .
C17 C 0.44484(15) 0.6160(2) 0.6652(3) 0.0886(9) Uani 1 1 d . . . . .
H17 H 0.4275 0.5904 0.7420 0.106 Uiso 1 1 calc R . . . .
C18 C 1.06503(12) 0.17022(19) -0.0386(3) 0.0737(7) Uani 1 1 d . . . . .
H18 H 1.1051 0.1826 -0.0508 0.088 Uiso 1 1 calc R . . . .
C19 C 1.03108(13) 0.11046(18) -0.1307(3) 0.0718(7) Uani 1 1 d . . . . .
H19 H 1.0481 0.0828 -0.2063 0.086 Uiso 1 1 calc R . . . .
C20 C 0.97184(11) 0.09079(16) -0.1124(2) 0.0590(6) Uani 1 1 d . . . . .
H20 H 0.9493 0.0502 -0.1758 0.071 Uiso 1 1 calc R . . . .
C21 C 0.94592(10) 0.13079(14) -0.0012(2) 0.0487(5) Uani 1 1 d . . . . .
C22 C 0.88223(10) 0.10698(14) 0.0225(2) 0.0556(6) Uani 1 1 d . . . . .
H22A H 0.8678 0.0559 -0.0414 0.067 Uiso 1 1 calc R . . . .
H22B H 0.8820 0.0850 0.1205 0.067 Uiso 1 1 calc R . . . .
C23 C 0.82131(10) 0.23582(14) 0.10292(19) 0.0450(5) Uani 1 1 d . . . . .
C24 C 0.78687(9) 0.32501(14) 0.0573(2) 0.0470(5) Uani 1 1 d . . . . .
H24 H 0.7656 0.3174 -0.0398 0.056 Uiso 1 1 calc R . . . .
C25 C 0.82725(10) 0.41031(14) 0.0632(2) 0.0461(5) Uani 1 1 d . . . . .
C26 C 0.87769(11) 0.42976(17) -0.0027(2) 0.0590(6) Uani 1 1 d . . . . .
H26 H 0.8923 0.3862 -0.0642 0.071 Uiso 1 1 calc R . . . .
C27 C 0.90642(12) 0.51614(19) 0.0249(3) 0.0728(7) Uani 1 1 d . . . . .
H27 H 0.9407 0.5305 -0.0186 0.087 Uiso 1 1 calc R . . . .
C28 C 0.88474(14) 0.58017(18) 0.1154(3) 0.0752(8) Uani 1 1 d . . . . .
H28 H 0.9044 0.6378 0.1309 0.090 Uiso 1 1 calc R . . . .
C29 C 0.98045(12) 0.19186(17) 0.0908(3) 0.0682(7) Uani 1 1 d . . . . .
H29 H 0.9636 0.2199 0.1665 0.082 Uiso 1 1 calc R . . . .
C30 C 1.03959(13) 0.21133(19) 0.0708(3) 0.0773(8) Uani 1 1 d . . . . .
H30 H 1.0622 0.2528 0.1326 0.093 Uiso 1 1 calc R . . . .
C31 C 0.83435(12) 0.56152(16) 0.1844(3) 0.0673(7) Uani 1 1 d . . . . .
H31 H 0.8200 0.6050 0.2466 0.081 Uiso 1 1 calc R . . . .
C32 C 0.80651(10) 0.47568(15) 0.1567(2) 0.0511(5) Uani 1 1 d . . . . .
C33 C 0.74215(11) 0.35019(17) 0.1619(2) 0.0557(6) Uani 1 1 d . . . . .
C34 C 0.72367(13) 0.4854(2) 0.3194(3) 0.0814(8) Uani 1 1 d . . . . .
H34A H 0.7032 0.5398 0.2766 0.122 Uiso 1 1 calc GR . . . .
H34B H 0.7518 0.5046 0.4000 0.122 Uiso 1 1 calc GR . . . .
H34C H 0.6946 0.4426 0.3515 0.122 Uiso 1 1 calc GR . . . .


_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 C6 1.231(2) . ?
O2 C15 1.219(3) . ?
O3 C33 1.218(3) . ?
O4 C23 1.231(2) . ?
N1 H1 0.8600 . ?
N1 C5 1.456(3) . ?
N1 C6 1.320(3) . ?
N2 C9 1.391(3) . ?
N2 C14 1.457(3) . ?
N2 C15 1.351(3) . ?
N3 H3A 0.8600 . ?
N3 C22 1.458(3) . ?
N3 C23 1.325(2) . ?
N4 C32 1.404(3) . ?
N4 C33 1.366(3) . ?
N4 C34 1.452(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.348(4) . ?
C1 C17 1.364(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 C5 1.505(3) . ?
C4 C16 1.376(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.519(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.493(3) . ?
C7 C15 1.520(3) . ?
C8 C9 1.391(3) . ?
C8 C12 1.373(3) . ?
C9 C10 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(5) . ?
C11 H11 0.9300 . ?
C11 C13 1.361(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.402(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.369(4) . ?
C18 C30 1.361(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(3) . ?
C21 C22 1.501(3) . ?
C21 C29 1.387(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.513(3) . ?
C24 H24 0.9800 . ?
C24 C25 1.504(3) . ?
C24 C33 1.521(3) . ?
C25 C26 1.373(3) . ?
C25 C32 1.392(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.369(4) . ?
C28 H28 0.9300 . ?
C28 C31 1.387(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.376(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C5 N1 H1 118.3 . . ?
C6 N1 H1 118.3 . . ?
C6 N1 C5 123.33(18) . . ?
C9 N2 C14 124.5(3) . . ?
C15 N2 C9 111.9(2) . . ?
C15 N2 C14 123.6(3) . . ?
C22 N3 H3A 118.5 . . ?
C23 N3 H3A 118.5 . . ?
C23 N3 C22 123.08(17) . . ?
C32 N4 C34 125.1(2) . . ?
C33 N4 C32 111.38(17) . . ?
C33 N4 C34 123.5(2) . . ?
C2 C1 H1A 119.9 . . ?
C2 C1 C17 120.2(3) . . ?
C17 C1 H1A 119.9 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 121.1(2) . . ?
C16 C4 C3 118.5(2) . . ?
C16 C4 C5 120.4(2) . . ?
N1 C5 C4 112.71(18) . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O1 C6 N1 123.8(2) . . ?
O1 C6 C7 120.20(19) . . ?
N1 C6 C7 115.95(17) . . ?
C6 C7 H7 110.8 . . ?
C6 C7 C15 108.61(16) . . ?
C8 C7 C6 112.65(17) . . ?
C8 C7 H7 110.8 . . ?
C8 C7 C15 103.04(18) . . ?
C15 C7 H7 110.8 . . ?
C9 C8 C7 108.0(2) . . ?
C12 C8 C7 130.8(2) . . ?
C12 C8 C9 121.2(2) . . ?
N2 C9 C8 109.5(2) . . ?
C10 C9 N2 129.6(3) . . ?
C10 C9 C8 120.9(3) . . ?
C9 C10 H10 121.5 . . ?
C9 C10 C11 117.0(3) . . ?
C11 C10 H10 121.5 . . ?
C10 C11 H11 118.7 . . ?
C13 C11 C10 122.6(4) . . ?
C13 C11 H11 118.7 . . ?
C8 C12 H12 121.0 . . ?
C8 C12 C13 117.9(3) . . ?
C13 C12 H12 121.0 . . ?
C11 C13 C12 120.3(4) . . ?
C11 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 N2 125.7(2) . . ?
O2 C15 C7 126.7(2) . . ?
N2 C15 C7 107.6(2) . . ?
C4 C16 H16 120.1 . . ?
C4 C16 C17 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C1 C17 C16 120.0(3) . . ?
C1 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 H18 120.3 . . ?
C30 C18 H18 120.3 . . ?
C30 C18 C19 119.4(3) . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 C29 118.5(2) . . ?
C29 C21 C22 120.8(2) . . ?
N3 C22 C21 112.80(17) . . ?
N3 C22 H22A 109.0 . . ?
N3 C22 H22B 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
O4 C23 N3 123.36(19) . . ?
O4 C23 C24 121.15(18) . . ?
N3 C23 C24 115.43(16) . . ?
C23 C24 H24 110.0 . . ?
C23 C24 C33 111.30(16) . . ?
C25 C24 C23 112.37(17) . . ?
C25 C24 H24 110.0 . . ?
C25 C24 C33 102.90(17) . . ?
C33 C24 H24 110.0 . . ?
C26 C25 C24 131.55(19) . . ?
C26 C25 C32 120.1(2) . . ?
C32 C25 C24 108.38(18) . . ?
C25 C26 H26 120.8 . . ?
C25 C26 C27 118.5(2) . . ?
C27 C26 H26 120.8 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.1 . . ?
C27 C28 C31 121.9(2) . . ?
C31 C28 H28 119.1 . . ?
C21 C29 H29 119.8 . . ?
C30 C29 C21 120.5(2) . . ?
C30 C29 H29 119.8 . . ?
C18 C30 C29 120.5(3) . . ?
C18 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C28 C31 H31 121.6 . . ?
C32 C31 C28 116.9(2) . . ?
C32 C31 H31 121.6 . . ?
C25 C32 N4 109.44(18) . . ?
C31 C32 N4 128.5(2) . . ?
C31 C32 C25 122.1(2) . . ?
O3 C33 N4 125.0(2) . . ?
O3 C33 C24 127.1(2) . . ?
N4 C33 C24 107.88(19) . . ?
N4 C34 H34A 109.5 . . ?
N4 C34 H34B 109.5 . . ?
N4 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
O1 C6 C7 C8 72.0(3) . . . . ?
O1 C6 C7 C15 -41.5(3) . . . . ?
O4 C23 C24 C25 85.2(2) . . . . ?
O4 C23 C24 C33 -29.6(3) . . . . ?
N1 C6 C7 C8 -108.2(2) . . . . ?
N1 C6 C7 C15 138.3(2) . . . . ?
N2 C9 C10 C11 -179.8(3) . . . . ?
N3 C23 C24 C25 -92.2(2) . . . . ?
N3 C23 C24 C33 153.00(18) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C1 C17 C16 -0.5(4) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C4 C16 -0.1(4) . . . . ?
C3 C4 C5 N1 70.6(3) . . . . ?
C3 C4 C16 C17 -0.1(4) . . . . ?
C4 C16 C17 C1 0.4(4) . . . . ?
C5 N1 C6 O1 -1.4(3) . . . . ?
C5 N1 C6 C7 178.83(18) . . . . ?
C5 C4 C16 C17 -178.5(2) . . . . ?
C6 N1 C5 C4 -108.5(2) . . . . ?
C6 C7 C8 C9 -115.78(19) . . . . ?
C6 C7 C8 C12 63.8(3) . . . . ?
C6 C7 C15 O2 -59.6(3) . . . . ?
C6 C7 C15 N2 118.04(19) . . . . ?
C7 C8 C9 N2 -0.2(2) . . . . ?
C7 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C12 C13 179.6(2) . . . . ?
C8 C7 C15 O2 -179.3(2) . . . . ?
C8 C7 C15 N2 -1.6(2) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C8 C12 C13 C11 0.6(5) . . . . ?
C9 N2 C15 O2 179.3(2) . . . . ?
C9 N2 C15 C7 1.7(2) . . . . ?
C9 C8 C12 C13 -0.8(4) . . . . ?
C9 C10 C11 C13 0.3(5) . . . . ?
C10 C11 C13 C12 -0.4(6) . . . . ?
C12 C8 C9 N2 -179.8(2) . . . . ?
C12 C8 C9 C10 0.8(3) . . . . ?
C14 N2 C9 C8 177.9(2) . . . . ?
C14 N2 C9 C10 -2.8(4) . . . . ?
C14 N2 C15 O2 0.5(4) . . . . ?
C14 N2 C15 C7 -177.2(2) . . . . ?
C15 N2 C9 C8 -1.0(3) . . . . ?
C15 N2 C9 C10 178.3(2) . . . . ?
C15 C7 C8 C9 1.1(2) . . . . ?
C15 C7 C8 C12 -179.3(2) . . . . ?
C16 C4 C5 N1 -111.0(2) . . . . ?
C17 C1 C2 C3 0.2(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C18 C30 C29 1.1(4) . . . . ?
C19 C20 C21 C22 -177.8(2) . . . . ?
C19 C20 C21 C29 0.6(3) . . . . ?
C20 C21 C22 N3 -113.4(2) . . . . ?
C20 C21 C29 C30 -0.3(4) . . . . ?
C21 C29 C30 C18 -0.6(4) . . . . ?
C22 N3 C23 O4 -6.3(3) . . . . ?
C22 N3 C23 C24 171.06(18) . . . . ?
C22 C21 C29 C30 178.1(2) . . . . ?
C23 N3 C22 C21 -104.1(2) . . . . ?
C23 C24 C25 C26 57.5(3) . . . . ?
C23 C24 C25 C32 -121.13(18) . . . . ?
C23 C24 C33 O3 -56.8(3) . . . . ?
C23 C24 C33 N4 121.81(19) . . . . ?
C24 C25 C26 C27 -179.4(2) . . . . ?
C24 C25 C32 N4 0.9(2) . . . . ?
C24 C25 C32 C31 -179.93(19) . . . . ?
C25 C24 C33 O3 -177.4(2) . . . . ?
C25 C24 C33 N4 1.3(2) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C26 C25 C32 N4 -177.86(18) . . . . ?
C26 C25 C32 C31 1.3(3) . . . . ?
C26 C27 C28 C31 1.0(4) . . . . ?
C27 C28 C31 C32 -0.7(4) . . . . ?
C28 C31 C32 N4 178.5(2) . . . . ?
C28 C31 C32 C25 -0.4(3) . . . . ?
C29 C21 C22 N3 68.3(3) . . . . ?
C30 C18 C19 C20 -0.8(4) . . . . ?
C32 N4 C33 O3 177.9(2) . . . . ?
C32 N4 C33 C24 -0.8(2) . . . . ?
C32 C25 C26 C27 -1.0(3) . . . . ?
C33 N4 C32 C25 -0.1(2) . . . . ?
C33 N4 C32 C31 -179.2(2) . . . . ?
C33 C24 C25 C26 177.3(2) . . . . ?
C33 C24 C25 C32 -1.3(2) . . . . ?
C34 N4 C32 C25 177.8(2) . . . . ?
C34 N4 C32 C31 -1.3(3) . . . . ?
C34 N4 C33 O3 0.0(4) . . . . ?
C34 N4 C33 C24 -178.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_20170607nch3_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1963638'
loop_
_audit_author_name
_audit_author_address
'jing linhai'
;china west normal university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_audit_creation_date             2017-07-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 N2 O5'
_chemical_formula_sum            'C28 H26 N2 O5'
_chemical_formula_weight         470.51
_chemical_absolute_configuration ad
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.1247(17)
_cell_length_b                   11.7728(18)
_cell_length_c                   18.015(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2359.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      63.87
_cell_measurement_theta_min      3.97
_exptl_absorpt_coefficient_mu    0.746
_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            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        63.866
_diffrn_reflns_theta_max         63.866
_diffrn_reflns_theta_min         4.486
_diffrn_ambient_temperature      149(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3679
_reflns_number_total             3889
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.3589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.83641(16) 0.08552(13) 0.26951(10) 0.0326(4) Uani 1 1 d . . . . .
O2 O 0.88856(16) 0.18506(13) 0.37087(10) 0.0323(4) Uani 1 1 d . . . . .
O3 O 0.69030(14) 0.25259(13) 0.22189(8) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.660(3) 0.185(3) 0.2149(15) 0.035 Uiso 1 1 d R . . . .
O4 O 0.45316(13) 0.56337(13) 0.31247(9) 0.0256(4) Uani 1 1 d . . . . .
O5 O 0.47047(14) 0.33094(15) 0.40120(10) 0.0334(4) Uani 1 1 d . . . . .
N1 N 0.63719(16) 0.25343(15) 0.34931(10) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.54163(17) 0.62439(16) 0.42123(11) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.6969(3) -0.0201(3) 0.5641(2) 0.0679(11) Uani 1 1 d . . . . .
H1 H 0.7213 -0.0550 0.6079 0.081 Uiso 1 1 calc R . . . .
C2 C 0.6375(3) 0.0819(3) 0.56598(17) 0.0604(9) Uani 1 1 d . . . . .
H2 H 0.6209 0.1163 0.6113 0.073 Uiso 1 1 calc R . . . .
C3 C 0.6022(3) 0.1336(2) 0.50055(15) 0.0409(6) Uani 1 1 d . . . . .
H3A H 0.5617 0.2026 0.5024 0.049 Uiso 1 1 calc R . . . .
C4 C 0.6264(2) 0.08428(19) 0.43246(13) 0.0258(5) Uani 1 1 d . . . . .
C5 C 0.5863(2) 0.13908(19) 0.36108(13) 0.0245(5) Uani 1 1 d . . . . .
H5A H 0.6096 0.0908 0.3199 0.029 Uiso 1 1 calc R . . . .
H5B H 0.4993 0.1445 0.3611 0.029 Uiso 1 1 calc R . . . .
C6 C 0.73463(18) 0.26323(17) 0.29450(11) 0.0183(4) Uani 1 1 d . . . . .
C7 C 0.79820(18) 0.37738(17) 0.29904(11) 0.0187(4) Uani 1 1 d . . . . .
H7A H 0.8456 0.3805 0.3442 0.022 Uiso 1 1 calc R . . . .
H7B H 0.8525 0.3852 0.2572 0.022 Uiso 1 1 calc R . . . .
C8 C 0.70882(18) 0.47503(17) 0.29857(11) 0.0173(4) Uani 1 1 d . . . . .
H8 H 0.6590 0.4667 0.2541 0.021 Uiso 1 1 calc R . . . .
C9 C 0.76841(19) 0.59106(18) 0.29473(11) 0.0186(4) Uani 1 1 d . . . . .
C10 C 0.8800(2) 0.61304(19) 0.32657(13) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.9197 0.5559 0.3524 0.031 Uiso 1 1 calc R . . . .
C11 C 0.9325(2) 0.7197(2) 0.32008(15) 0.0339(6) Uani 1 1 d . . . . .
H11 H 1.0078 0.7327 0.3408 0.041 Uiso 1 1 calc R . . . .
C12 C 0.8742(2) 0.80627(19) 0.28317(14) 0.0323(6) Uani 1 1 d . . . . .
H12 H 0.9097 0.8775 0.2792 0.039 Uiso 1 1 calc R . . . .
C13 C 0.7198(4) -0.0702(3) 0.4966(3) 0.0707(11) Uani 1 1 d . . . . .
H13 H 0.7595 -0.1396 0.4951 0.085 Uiso 1 1 calc R . . . .
C14 C 0.6848(3) -0.0191(2) 0.43114(18) 0.0468(7) Uani 1 1 d . . . . .
H14 H 0.7007 -0.0544 0.3860 0.056 Uiso 1 1 calc R . . . .
C15 C 0.56846(18) 0.34297(18) 0.37160(12) 0.0205(5) Uani 1 1 d . . . . .
C16 C 0.62506(18) 0.46120(17) 0.36703(12) 0.0185(4) Uani 1 1 d . . . . .
C17 C 0.82587(19) 0.16579(17) 0.30925(12) 0.0213(4) Uani 1 1 d . . . . .
C18 C 0.9767(3) 0.0989(2) 0.38991(19) 0.0489(8) Uani 1 1 d . . . . .
H18A H 0.9407 0.0250 0.3860 0.073 Uiso 1 1 calc GR . . . .
H18B H 1.0041 0.1108 0.4398 0.073 Uiso 1 1 calc GR . . . .
H18C H 1.0437 0.1038 0.3564 0.073 Uiso 1 1 calc GR . . . .
C19 C 0.7114(2) 0.67941(19) 0.25735(13) 0.0269(5) Uani 1 1 d . . . . .
H19 H 0.6370 0.6663 0.2354 0.032 Uiso 1 1 calc R . . . .
C20 C 0.7626(2) 0.78622(19) 0.25210(15) 0.0326(6) Uani 1 1 d . . . . .
H20 H 0.7221 0.8444 0.2277 0.039 Uiso 1 1 calc R . . . .
C21 C 0.52678(19) 0.55323(18) 0.36263(12) 0.0203(4) Uani 1 1 d . . . . .
C22 C 0.63079(19) 0.58430(19) 0.46988(12) 0.0223(5) Uani 1 1 d . . . . .
C23 C 0.68223(19) 0.48571(18) 0.44184(11) 0.0199(4) Uani 1 1 d . . . . .
C24 C 0.7635(2) 0.4252(2) 0.48378(12) 0.0279(5) Uani 1 1 d . . . . .
H24 H 0.7965 0.3579 0.4662 0.033 Uiso 1 1 calc R . . . .
C25 C 0.7950(2) 0.4677(2) 0.55339(14) 0.0354(6) Uani 1 1 d . . . . .
H25 H 0.8495 0.4278 0.5826 0.042 Uiso 1 1 calc R . . . .
C26 C 0.7466(2) 0.5677(2) 0.57952(13) 0.0335(6) Uani 1 1 d . . . . .
H26 H 0.7706 0.5953 0.6256 0.040 Uiso 1 1 calc R . . . .
C27 C 0.6629(2) 0.6279(2) 0.53832(13) 0.0293(5) Uani 1 1 d . . . . .
H27 H 0.6295 0.6950 0.5561 0.035 Uiso 1 1 calc R . . . .
C28 C 0.4757(2) 0.7295(2) 0.43127(16) 0.0382(6) Uani 1 1 d . . . . .
H28A H 0.5245 0.7922 0.4155 0.057 Uiso 1 1 calc GR . . . .
H28B H 0.4555 0.7385 0.4827 0.057 Uiso 1 1 calc GR . . . .
H28C H 0.4034 0.7273 0.4022 0.057 Uiso 1 1 calc GR . . . .


_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 C17 1.191(3) . ?
O2 C17 1.331(3) . ?
O2 C18 1.452(3) . ?
O3 H3 0.87(3) . ?
O3 C6 1.404(2) . ?
O4 C21 1.225(3) . ?
O5 C15 1.222(3) . ?
N1 C5 1.476(3) . ?
N1 C6 1.471(3) . ?
N1 C15 1.363(3) . ?
N2 C21 1.358(3) . ?
N2 C22 1.405(3) . ?
N2 C28 1.449(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(6) . ?
C1 C13 1.375(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.383(4) . ?
C4 C5 1.506(3) . ?
C4 C14 1.380(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.521(3) . ?
C6 C17 1.555(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.520(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.520(3) . ?
C8 C16 1.554(3) . ?
C9 C10 1.391(3) . ?
C9 C19 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C20 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.530(3) . ?
C16 C21 1.541(3) . ?
C16 C23 1.518(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C22 C23 1.389(3) . ?
C22 C27 1.382(3) . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.395(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.386(4) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C17 O2 C18 115.59(19) . . ?
C6 O3 H3 110.6(18) . . ?
C6 N1 C5 116.78(17) . . ?
C15 N1 C5 116.63(18) . . ?
C15 N1 C6 123.41(17) . . ?
C21 N2 C22 111.32(18) . . ?
C21 N2 C28 124.2(2) . . ?
C22 N2 C28 124.5(2) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C13 119.1(3) . . ?
C13 C1 H1 120.4 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 121.3(2) . . ?
C14 C4 C3 118.5(2) . . ?
C14 C4 C5 120.2(2) . . ?
N1 C5 C4 113.58(18) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O3 C6 N1 111.08(16) . . ?
O3 C6 C7 107.00(16) . . ?
O3 C6 C17 108.83(16) . . ?
N1 C6 C7 112.08(16) . . ?
N1 C6 C17 107.97(16) . . ?
C7 C6 C17 109.83(16) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.34(16) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8 107.4 . . ?
C7 C8 C16 107.97(16) . . ?
C9 C8 C7 113.25(17) . . ?
C9 C8 H8 107.4 . . ?
C9 C8 C16 113.06(16) . . ?
C16 C8 H8 107.4 . . ?
C10 C9 C8 122.51(19) . . ?
C10 C9 C19 117.8(2) . . ?
C19 C9 C8 119.65(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C20 119.4(2) . . ?
C20 C12 H12 120.3 . . ?
C1 C13 H13 119.4 . . ?
C1 C13 C14 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C4 C14 H14 119.9 . . ?
C13 C14 C4 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
O5 C15 N1 122.7(2) . . ?
O5 C15 C16 119.7(2) . . ?
N1 C15 C16 117.19(17) . . ?
C15 C16 C8 112.63(17) . . ?
C15 C16 C21 110.51(17) . . ?
C21 C16 C8 108.11(16) . . ?
C23 C16 C8 115.69(16) . . ?
C23 C16 C15 107.31(17) . . ?
C23 C16 C21 102.08(16) . . ?
O1 C17 O2 125.8(2) . . ?
O1 C17 C6 123.2(2) . . ?
O2 C17 C6 111.04(17) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19 119.2 . . ?
C20 C19 C9 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C12 C20 C19 119.8(2) . . ?
C12 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O4 C21 N2 126.48(19) . . ?
O4 C21 C16 125.49(19) . . ?
N2 C21 C16 107.91(18) . . ?
C23 C22 N2 110.15(19) . . ?
C27 C22 N2 127.9(2) . . ?
C27 C22 C23 121.9(2) . . ?
C22 C23 C16 108.00(18) . . ?
C24 C23 C16 131.6(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 H24 120.9 . . ?
C23 C24 C25 118.3(2) . . ?
C25 C24 H24 120.9 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.1(2) . . ?
C27 C26 H26 119.5 . . ?
C22 C27 C26 117.5(2) . . ?
C22 C27 H27 121.3 . . ?
C26 C27 H27 121.3 . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O3 C6 C7 C8 72.1(2) . . . . ?
O3 C6 C17 O1 -12.8(3) . . . . ?
O3 C6 C17 O2 167.11(17) . . . . ?
O5 C15 C16 C8 -151.2(2) . . . . ?
O5 C15 C16 C21 -30.2(3) . . . . ?
O5 C15 C16 C23 80.3(2) . . . . ?
N1 C6 C7 C8 -49.9(2) . . . . ?
N1 C6 C17 O1 107.9(2) . . . . ?
N1 C6 C17 O2 -72.2(2) . . . . ?
N1 C15 C16 C8 35.9(2) . . . . ?
N1 C15 C16 C21 156.94(18) . . . . ?
N1 C15 C16 C23 -92.5(2) . . . . ?
N2 C22 C23 C16 2.2(2) . . . . ?
N2 C22 C23 C24 -173.6(2) . . . . ?
N2 C22 C27 C26 174.3(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C13 C14 C4 0.4(5) . . . . ?
C2 C1 C13 C14 0.4(5) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C4 C14 1.1(4) . . . . ?
C3 C4 C5 N1 60.2(3) . . . . ?
C3 C4 C14 C13 -1.1(4) . . . . ?
C5 N1 C6 O3 72.9(2) . . . . ?
C5 N1 C6 C7 -167.42(17) . . . . ?
C5 N1 C6 C17 -46.3(2) . . . . ?
C5 N1 C15 O5 1.3(3) . . . . ?
C5 N1 C15 C16 173.98(18) . . . . ?
C5 C4 C14 C13 -179.0(3) . . . . ?
C6 N1 C5 C4 104.8(2) . . . . ?
C6 N1 C15 O5 160.5(2) . . . . ?
C6 N1 C15 C16 -26.8(3) . . . . ?
C6 C7 C8 C9 -173.87(16) . . . . ?
C6 C7 C8 C16 60.2(2) . . . . ?
C7 C6 C17 O1 -129.6(2) . . . . ?
C7 C6 C17 O2 50.3(2) . . . . ?
C7 C8 C9 C10 -32.0(3) . . . . ?
C7 C8 C9 C19 147.1(2) . . . . ?
C7 C8 C16 C15 -52.2(2) . . . . ?
C7 C8 C16 C21 -174.61(16) . . . . ?
C7 C8 C16 C23 71.7(2) . . . . ?
C8 C9 C10 C11 178.3(2) . . . . ?
C8 C9 C19 C20 -179.6(2) . . . . ?
C8 C16 C21 O4 61.0(3) . . . . ?
C8 C16 C21 N2 -115.11(19) . . . . ?
C8 C16 C23 C22 111.5(2) . . . . ?
C8 C16 C23 C24 -73.5(3) . . . . ?
C9 C8 C16 C15 -178.31(16) . . . . ?
C9 C8 C16 C21 59.3(2) . . . . ?
C9 C8 C16 C23 -54.4(2) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C9 C19 C20 C12 1.3(4) . . . . ?
C10 C9 C19 C20 -0.4(3) . . . . ?
C10 C11 C12 C20 -0.3(4) . . . . ?
C11 C12 C20 C19 -0.9(4) . . . . ?
C13 C1 C2 C3 -0.5(5) . . . . ?
C14 C4 C5 N1 -122.0(2) . . . . ?
C15 N1 C5 C4 -94.6(2) . . . . ?
C15 N1 C6 O3 -86.2(2) . . . . ?
C15 N1 C6 C7 33.4(3) . . . . ?
C15 N1 C6 C17 154.53(18) . . . . ?
C15 C16 C21 O4 -62.7(3) . . . . ?
C15 C16 C21 N2 121.21(19) . . . . ?
C15 C16 C23 C22 -121.84(18) . . . . ?
C15 C16 C23 C24 53.2(3) . . . . ?
C16 C8 C9 C10 91.2(2) . . . . ?
C16 C8 C9 C19 -89.6(2) . . . . ?
C16 C23 C24 C25 -176.6(2) . . . . ?
C17 C6 C7 C8 -169.93(16) . . . . ?
C18 O2 C17 O1 -0.1(3) . . . . ?
C18 O2 C17 C6 180.0(2) . . . . ?
C19 C9 C10 C11 -0.8(3) . . . . ?
C21 N2 C22 C23 2.9(2) . . . . ?
C21 N2 C22 C27 -173.5(2) . . . . ?
C21 C16 C23 C22 -5.6(2) . . . . ?
C21 C16 C23 C24 169.4(2) . . . . ?
C22 N2 C21 O4 177.4(2) . . . . ?
C22 N2 C21 C16 -6.6(2) . . . . ?
C22 C23 C24 C25 -2.1(3) . . . . ?
C23 C16 C21 O4 -176.6(2) . . . . ?
C23 C16 C21 N2 7.3(2) . . . . ?
C23 C22 C27 C26 -1.7(3) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C24 C25 C26 C27 1.6(4) . . . . ?
C25 C26 C27 C22 -0.6(4) . . . . ?
C27 C22 C23 C16 178.9(2) . . . . ?
C27 C22 C23 C24 3.1(3) . . . . ?
C28 N2 C21 O4 -3.9(4) . . . . ?
C28 N2 C21 C16 172.2(2) . . . . ?
C28 N2 C22 C23 -175.8(2) . . . . ?
C28 N2 C22 C27 7.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
