# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_3-sad
_database_code_depnum_ccdc_archive 'CCDC 1955986'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Liu'
;University of Jinan
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2019-11-19 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            'C27 H27 N O6'
_chemical_formula_weight         461.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1938(3)
_cell_length_b                   9.8306(2)
_cell_length_c                   17.9027(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.5890(10)
_cell_angle_gamma                90
_cell_volume                     2447.10(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6455
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      63.65

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker, 2005)'
_exptl_absorpt_special_details   
;
about 2 hours for data collection, 
with scale.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            11170
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.158
_diffrn_reflns_theta_max         63.702
_diffrn_reflns_theta_full        63.702
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3890
_reflns_number_gt                3175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3890
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.54907(8) 0.94742(12) 0.39760(7) 0.0563(3) Uani 1 1 d . . . . .
O5 O 0.83803(7) 0.51644(11) 0.55857(6) 0.0486(3) Uani 1 1 d . . . . .
O1 O 0.37810(15) 0.8971(3) 0.26189(13) 0.1243(7) Uani 1 1 d . . . . .
O2 O 0.61390(11) 0.97384(16) 0.29409(9) 0.0801(4) Uani 1 1 d . . . . .
O4 O 0.71800(8) 0.64059(13) 0.49818(8) 0.0644(4) Uani 1 1 d . . . . .
O6 O 0.81440(10) 1.13629(14) 0.43131(13) 0.0999(6) Uani 1 1 d . . . . .
N1 N 1.08296(11) 0.22615(15) 0.69282(9) 0.0566(4) Uani 1 1 d . . . . .
C18 C 1.00178(11) 0.59466(16) 0.58026(9) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.2709(2) 0.7390(5) 0.2990(3) 0.1709(18) Uani 1 1 d . . . . .
H1C H 0.2332 0.8094 0.3158 0.256 Uiso 1 1 calc R U . . .
H1A H 0.2773 0.6641 0.3340 0.256 Uiso 1 1 calc R U . . .
H1B H 0.2396 0.7086 0.2492 0.256 Uiso 1 1 calc R U . . .
C2 C 0.36845(18) 0.7934(3) 0.29564(17) 0.0936(8) Uani 1 1 d . . . . .
C3 C 0.45237(17) 0.7141(2) 0.33600(15) 0.0834(7) Uani 1 1 d . . . . .
H3A H 0.4418 0.6188 0.3231 0.100 Uiso 1 1 calc R U . . .
H3B H 0.4563 0.7231 0.3905 0.100 Uiso 1 1 calc R U . . .
C4 C 0.54742(16) 0.7573(2) 0.31755(15) 0.0783(6) Uani 1 1 d . . . . .
H4B H 0.5980 0.7024 0.3475 0.094 Uiso 1 1 calc R U . . .
H4A H 0.5460 0.7376 0.2642 0.094 Uiso 1 1 calc R U . . .
C5 C 0.57287(13) 0.9030(2) 0.33160(11) 0.0598(5) Uani 1 1 d . . . . .
C6 C 0.56123(12) 1.08617(18) 0.41601(10) 0.0514(4) Uani 1 1 d . . . . .
C11 C 0.65140(12) 1.14570(18) 0.43764(10) 0.0535(4) Uani 1 1 d . . . . .
C12 C 0.74562(12) 1.07272(19) 0.44449(12) 0.0611(5) Uani 1 1 d . . . . .
C13 C 0.75544(12) 0.93160(17) 0.47082(10) 0.0524(4) Uani 1 1 d . . . . .
H13 H 0.7015 0.8818 0.4763 0.063 Uiso 1 1 calc R U . . .
C14 C 0.84270(12) 0.87504(17) 0.48686(9) 0.0489(4) Uani 1 1 d . . . . .
H14 H 0.8919 0.9297 0.4763 0.059 Uiso 1 1 calc R U . . .
C16 C 0.87313(11) 0.74335(16) 0.51783(9) 0.0438(4) Uani 1 1 d . . . . .
C15 C 0.80338(12) 0.63644(16) 0.52246(9) 0.0468(4) Uani 1 1 d . . . . .
C19 C 0.93439(11) 0.49471(16) 0.58815(9) 0.0418(4) Uani 1 1 d . . . . .
C20 C 0.95890(11) 0.37364(16) 0.62447(9) 0.0467(4) Uani 1 1 d . . . . .
H20 H 0.9115 0.3104 0.6287 0.056 Uiso 1 1 calc R U . . .
C21 C 1.05644(12) 0.34492(17) 0.65557(9) 0.0466(4) Uani 1 1 d . . . . .
C24 C 1.01260(15) 0.1337(2) 0.71453(11) 0.0649(5) Uani 1 1 d . . . . .
H24B H 0.9579 0.1861 0.7233 0.078 Uiso 1 1 calc R U . . .
H24A H 1.0413 0.0893 0.7620 0.078 Uiso 1 1 calc R U . . .
C25 C 0.9780(2) 0.0274(3) 0.65548(16) 0.0958(8) Uani 1 1 d . . . . .
H25A H 0.9499 0.0706 0.6081 0.144 Uiso 1 1 calc R U . . .
H25B H 0.9306 -0.0285 0.6720 0.144 Uiso 1 1 calc R U . . .
H25C H 1.0312 -0.0281 0.6485 0.144 Uiso 1 1 calc R U . . .
C7 C 0.47819(13) 1.1600(2) 0.41266(12) 0.0661(5) Uani 1 1 d . . . . .
H7 H 0.4186 1.1180 0.3985 0.079 Uiso 1 1 calc R U . . .
C8 C 0.48376(15) 1.2969(2) 0.43047(13) 0.0755(6) Uani 1 1 d . . . . .
H8 H 0.4278 1.3470 0.4288 0.091 Uiso 1 1 calc R U . . .
C9 C 0.57140(15) 1.3589(2) 0.45047(13) 0.0709(6) Uani 1 1 d . . . . .
H9 H 0.5751 1.4513 0.4617 0.085 Uiso 1 1 calc R U . . .
C10 C 0.65392(14) 1.28419(19) 0.45400(12) 0.0635(5) Uani 1 1 d . . . . .
H10 H 0.7132 1.3274 0.4677 0.076 Uiso 1 1 calc R U . . .
C17 C 0.96837(11) 0.71732(16) 0.54433(9) 0.0441(4) Uani 1 1 d . . . . .
H17 H 1.0130 0.7836 0.5383 0.053 Uiso 1 1 calc R U . . .
C23 C 1.09886(11) 0.56437(17) 0.61105(9) 0.0479(4) Uani 1 1 d . . . . .
H23 H 1.1459 0.6279 0.6065 0.057 Uiso 1 1 calc R U . . .
C22 C 1.12556(12) 0.44483(17) 0.64722(10) 0.0495(4) Uani 1 1 d . . . . .
H22 H 1.1903 0.4283 0.6668 0.059 Uiso 1 1 calc R U . . .
C26 C 1.18360(13) 0.1868(2) 0.71639(11) 0.0637(5) Uani 1 1 d . . . . .
H26A H 1.2190 0.2202 0.6791 0.076 Uiso 1 1 calc R U . . .
H26B H 1.1879 0.0883 0.7169 0.076 Uiso 1 1 calc R U . . .
C27 C 1.23040(18) 0.2401(3) 0.79384(13) 0.0927(8) Uani 1 1 d . . . . .
H27C H 1.2384 0.3368 0.7912 0.139 Uiso 1 1 calc R U . . .
H27B H 1.2921 0.1978 0.8100 0.139 Uiso 1 1 calc R U . . .
H27A H 1.1905 0.2196 0.8298 0.139 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
O3 C5 1.364(2) . ?
O3 C6 1.406(2) . ?
O5 C19 1.3805(18) . ?
O5 C15 1.3870(19) . ?
O1 C2 1.207(3) . ?
O2 C5 1.197(2) . ?
O4 C15 1.2031(19) . ?
O6 C12 1.221(2) . ?
N1 C21 1.360(2) . ?
N1 C26 1.458(2) . ?
N1 C24 1.460(2) . ?
C18 C19 1.398(2) . ?
C18 C17 1.404(2) . ?
C18 C23 1.409(2) . ?
C1 C2 1.497(4) . ?
C1 H1C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C2 C3 1.484(4) . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.486(3) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C6 C7 1.376(3) . ?
C6 C11 1.390(2) . ?
C11 C10 1.392(3) . ?
C11 C12 1.501(2) . ?
C12 C13 1.463(3) . ?
C13 C14 1.335(2) . ?
C13 H13 0.9300 . ?
C14 C16 1.440(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.364(2) . ?
C16 C15 1.458(2) . ?
C19 C20 1.367(2) . ?
C20 C21 1.413(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.417(2) . ?
C24 C25 1.498(3) . ?
C24 H24B 0.9700 . ?
C24 H24A 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C23 C22 1.358(2) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C26 C27 1.506(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27C 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27A 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 O3 C6 118.28(14) . . ?
C19 O5 C15 122.79(12) . . ?
C21 N1 C26 121.90(15) . . ?
C21 N1 C24 121.90(15) . . ?
C26 N1 C24 116.15(15) . . ?
C19 C18 C17 118.36(14) . . ?
C19 C18 C23 116.56(14) . . ?
C17 C18 C23 125.07(14) . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C2 C3 121.8(2) . . ?
O1 C2 C1 121.4(3) . . ?
C3 C2 C1 116.9(3) . . ?
C2 C3 C4 114.2(2) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 115.52(19) . . ?
C5 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
H4B C4 H4A 107.5 . . ?
O2 C5 O3 122.18(18) . . ?
O2 C5 C4 126.5(2) . . ?
O3 C5 C4 111.17(18) . . ?
C7 C6 C11 121.53(17) . . ?
C7 C6 O3 115.99(15) . . ?
C11 C6 O3 122.47(15) . . ?
C6 C11 C10 117.00(16) . . ?
C6 C11 C12 125.25(16) . . ?
C10 C11 C12 117.76(16) . . ?
O6 C12 C13 121.29(16) . . ?
O6 C12 C11 118.24(16) . . ?
C13 C12 C11 120.36(15) . . ?
C14 C13 C12 119.24(15) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C16 130.60(16) . . ?
C13 C14 H14 114.7 . . ?
C16 C14 H14 114.7 . . ?
C17 C16 C14 120.16(14) . . ?
C17 C16 C15 118.81(15) . . ?
C14 C16 C15 121.03(14) . . ?
O4 C15 O5 115.75(14) . . ?
O4 C15 C16 126.97(16) . . ?
O5 C15 C16 117.29(14) . . ?
C20 C19 O5 117.06(14) . . ?
C20 C19 C18 123.09(15) . . ?
O5 C19 C18 119.85(14) . . ?
C19 C20 C21 119.79(15) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
N1 C21 C20 121.18(15) . . ?
N1 C21 C22 121.16(15) . . ?
C20 C21 C22 117.65(15) . . ?
N1 C24 C25 113.07(18) . . ?
N1 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
N1 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
H24B C24 H24A 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C6 C7 C8 119.69(18) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.08(18) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.81(19) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 121.86(18) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C16 C17 C18 122.73(14) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C22 C23 C18 121.76(15) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 119.1 . . ?
C23 C22 C21 121.14(15) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
N1 C26 C27 113.54(18) . . ?
N1 C26 H26A 108.9 . . ?
C27 C26 H26A 108.9 . . ?
N1 C26 H26B 108.9 . . ?
C27 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 H27C 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27C C27 H27B 109.5 . . ?
C26 C27 H27A 109.5 . . ?
H27C C27 H27A 109.5 . . ?
H27B C27 H27A 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 C2 C3 C4 -12.1(4) . . . . ?
C1 C2 C3 C4 168.2(3) . . . . ?
C2 C3 C4 C5 56.4(3) . . . . ?
C6 O3 C5 O2 9.0(3) . . . . ?
C6 O3 C5 C4 -174.87(15) . . . . ?
C3 C4 C5 O2 -143.8(2) . . . . ?
C3 C4 C5 O3 40.3(3) . . . . ?
C5 O3 C6 C7 110.93(18) . . . . ?
C5 O3 C6 C11 -70.1(2) . . . . ?
C7 C6 C11 C10 -1.5(3) . . . . ?
O3 C6 C11 C10 179.62(17) . . . . ?
C7 C6 C11 C12 178.65(18) . . . . ?
O3 C6 C11 C12 -0.2(3) . . . . ?
C6 C11 C12 O6 148.8(2) . . . . ?
C10 C11 C12 O6 -31.0(3) . . . . ?
C6 C11 C12 C13 -34.8(3) . . . . ?
C10 C11 C12 C13 145.31(19) . . . . ?
O6 C12 C13 C14 5.7(3) . . . . ?
C11 C12 C13 C14 -170.52(17) . . . . ?
C12 C13 C14 C16 175.58(18) . . . . ?
C13 C14 C16 C17 -166.28(17) . . . . ?
C13 C14 C16 C15 12.9(3) . . . . ?
C19 O5 C15 O4 178.69(14) . . . . ?
C19 O5 C15 C16 -1.3(2) . . . . ?
C17 C16 C15 O4 -175.79(16) . . . . ?
C14 C16 C15 O4 5.0(3) . . . . ?
C17 C16 C15 O5 4.2(2) . . . . ?
C14 C16 C15 O5 -174.97(14) . . . . ?
C15 O5 C19 C20 178.01(14) . . . . ?
C15 O5 C19 C18 -1.9(2) . . . . ?
C17 C18 C19 C20 -177.72(15) . . . . ?
C23 C18 C19 C20 0.9(2) . . . . ?
C17 C18 C19 O5 2.2(2) . . . . ?
C23 C18 C19 O5 -179.20(13) . . . . ?
O5 C19 C20 C21 179.61(13) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C26 N1 C21 C20 171.74(16) . . . . ?
C24 N1 C21 C20 -11.1(3) . . . . ?
C26 N1 C21 C22 -8.9(3) . . . . ?
C24 N1 C21 C22 168.30(16) . . . . ?
C19 C20 C21 N1 179.20(15) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C21 N1 C24 C25 92.0(2) . . . . ?
C26 N1 C24 C25 -90.7(2) . . . . ?
C11 C6 C7 C8 0.6(3) . . . . ?
O3 C6 C7 C8 179.51(18) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C6 C11 C10 C9 1.2(3) . . . . ?
C12 C11 C10 C9 -178.94(19) . . . . ?
C14 C16 C17 C18 175.12(14) . . . . ?
C15 C16 C17 C18 -4.1(2) . . . . ?
C19 C18 C17 C16 0.9(2) . . . . ?
C23 C18 C17 C16 -177.64(15) . . . . ?
C19 C18 C23 C22 -0.7(2) . . . . ?
C17 C18 C23 C22 177.87(16) . . . . ?
C18 C23 C22 C21 0.0(3) . . . . ?
N1 C21 C22 C23 -178.95(16) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 N1 C26 C27 87.7(2) . . . . ?
C24 N1 C26 C27 -89.6(2) . . . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1955987'
loop_
_audit_author_name
_audit_author_address
'Zhiqiang Liu'
;University of Jinan
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21.75 N3 O3'
_chemical_formula_weight         376.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   17.6924(11)
_cell_length_b                   6.6868(4)
_cell_length_c                   15.2410(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1803.09(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6812
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      72.41

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             795
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.759
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12901
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.828
_diffrn_reflns_theta_max         72.438
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3549
_reflns_number_gt                3169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.2611P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3549
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0991
_refine_ls_wR_factor_ref         0.2303
_refine_ls_wR_factor_gt          0.2245
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C00A C 0.3118(4) 0.4953(10) 0.3643(4) 0.0217(14) Uani 1 1 d . . . . .
C00B C 0.2586(4) 0.8810(12) 0.6620(5) 0.0291(17) Uani 1 1 d . . . . .
C00C C 0.3473(4) 0.5711(11) 0.7305(5) 0.0244(15) Uani 1 1 d . . . . .
C00D C 0.3933(5) 0.2818(14) 0.2785(5) 0.037(2) Uani 1 1 d . . . . .
H00D H 0.412055 0.152376 0.264889 0.044 Uiso 1 1 calc R U . . .
C00E C 0.4066(4) 0.8199(12) 0.8236(5) 0.0267(16) Uani 1 1 d . . . . .
H00E H 0.409603 0.955034 0.842572 0.032 Uiso 1 1 calc R U . . .
C00F C 0.3411(5) 0.6600(12) 0.3178(5) 0.0309(18) Uani 1 1 d . . . . .
H00F H 0.323204 0.790605 0.330862 0.037 Uiso 1 1 calc R U . . .
C00G C 0.2247(5) 0.7176(12) 0.4681(5) 0.0300(18) Uani 1 1 d . . . . .
H00A H 0.185150 0.772508 0.428974 0.036 Uiso 1 1 calc R U . . .
H00B H 0.265311 0.818064 0.475674 0.036 Uiso 1 1 calc R U . . .
C00H C 0.3369(4) 0.3045(13) 0.3422(5) 0.0294(17) Uani 1 1 d . . . . .
C00I C 0.1919(5) 0.6517(12) 0.5564(5) 0.0318(18) Uani 1 1 d . . . . .
H00I H 0.144196 0.726001 0.569887 0.038 Uiso 1 1 calc R U . . .
C00J C 0.4213(5) 0.4457(17) 0.2359(6) 0.045(2) Uani 1 1 d . . . . .
H00J H 0.459654 0.428853 0.192948 0.054 Uiso 1 1 calc R U . . .
C00K C 0.3947(5) 0.6354(13) 0.2542(5) 0.0343(19) Uani 1 1 d . . . . .
H00K H 0.413539 0.747671 0.222831 0.041 Uiso 1 1 calc R U . . .
C00L C 0.4648(5) 0.9620(14) 1.0324(6) 0.041(2) Uani 1 1 d . . . . .
H00C H 0.412337 0.947802 1.012714 0.061 Uiso 1 1 calc R U . . .
H00G H 0.473152 1.098562 1.053536 0.061 Uiso 1 1 calc R U . . .
H00H H 0.474738 0.866968 1.079948 0.061 Uiso 1 1 calc R U . . .
C00M C 0.5183(5) 0.9190(19) 0.9555(7) 0.058(3) Uani 1 1 d . . . . .
H00L H 0.508318 1.016797 0.908158 0.069 Uiso 1 1 calc R U . . .
H00M H 0.571041 0.938486 0.975423 0.069 Uiso 1 1 calc R U . . .
C00N C 0.4553(5) 0.6758(16) 0.8602(7) 0.047(2) Uani 1 1 d . . . . .
C00O C 0.3926(5) 0.4281(13) 0.7672(6) 0.041(2) Uani 1 1 d . . . . .
H00O H 0.387123 0.292823 0.749259 0.049 Uiso 1 1 calc R U . . .
C00Q C 0.4465(6) 0.4755(18) 0.8301(7) 0.062(3) Uani 1 1 d . . . . .
H00Q H 0.477860 0.373052 0.853286 0.074 Uiso 1 1 calc R U . . .
C1B C 0.5959(12) 0.414(3) 0.9609(14) 0.043(5) Uani 0.45 1 d . . P . .
C1A C 0.5723(8) 0.598(3) 0.9414(10) 0.047(5) Uani 0.55 1 d . . P . .
H1B1 H 0.587454 0.510541 0.891923 0.056 Uiso 0.5 1 d R U P . .
H1B2 H 0.616458 0.672775 0.963738 0.056 Uiso 0.5 1 d R U P . .
C2B C 0.5354(6) 0.495(2) 1.0055(8) 0.071(4) Uani 1 1 d . . . . .
H2B1 H 0.567322 0.391420 1.031966 0.106 Uiso 1 1 d R U . . .
H2B2 H 0.521291 0.593133 1.050351 0.106 Uiso 1 1 d R U . . .
H2B3 H 0.489595 0.433133 0.981476 0.106 Uiso 1 1 d R U . . .
C006 C 0.2499(4) 0.6788(11) 0.6300(5) 0.0259(15) Uani 1 1 d . . . . .
C007 C 0.3552(4) 0.7666(11) 0.7612(5) 0.0244(16) Uani 1 1 d . . . . .
C008 C 0.2552(4) 0.5228(12) 0.4341(4) 0.0237(15) Uani 1 1 d . . . . .
C009 C 0.2928(4) 0.5324(11) 0.6640(5) 0.0237(15) Uani 1 1 d . . . . .
H009 H 0.286546 0.399551 0.643165 0.028 Uiso 1 1 calc R U . . .
N00P N 0.5107(6) 0.7212(18) 0.9207(7) 0.086(4) Uani 1 1 d . . . . .
N004 N 0.2273(4) 0.3723(10) 0.4764(4) 0.0295(15) Uani 1 1 d . . . . .
N005 N 0.1762(4) 0.4408(11) 0.5385(4) 0.0342(16) Uani 1 1 d . . . . .
H005 H 0.140255 0.369173 0.563080 0.041 Uiso 1 1 calc R U . . .
O001 O 0.3107(3) 0.9161(8) 0.7282(4) 0.0309(12) Uani 1 1 d . . . . .
O002 O 0.2246(4) 1.0277(9) 0.6356(4) 0.0400(14) Uani 1 1 d . . . . .
O003 O 0.3104(3) 0.1369(8) 0.3826(4) 0.0360(14) Uani 1 1 d . . . . .
H003 H 0.286462 0.169255 0.427975 0.054 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
C00A C00H 1.391(10) . ?
C00A C00F 1.409(10) . ?
C00A C008 1.473(10) . ?
C00B O002 1.219(9) . ?
C00B O001 1.386(9) . ?
C00B C006 1.446(11) . ?
C00C C00O 1.368(11) . ?
C00C C007 1.396(10) . ?
C00C C009 1.422(10) . ?
C00D C00J 1.367(14) . ?
C00D C00H 1.400(11) . ?
C00E C007 1.364(10) . ?
C00E C00N 1.407(12) . ?
C00F C00K 1.366(12) . ?
C00G C008 1.502(11) . ?
C00G C00I 1.531(10) . ?
C00H O003 1.362(10) . ?
C00I N005 1.463(11) . ?
C00I C006 1.531(11) . ?
C00J C00K 1.381(14) . ?
C00L C00M 1.532(13) . ?
C00M N00P 1.431(15) . ?
C00N N00P 1.380(12) . ?
C00N C00Q 1.425(15) . ?
C00O C00Q 1.387(12) . ?
C1B C2B 1.38(2) . ?
C1A C2B 1.36(2) . ?
C1A N00P 1.40(2) . ?
C006 C009 1.342(10) . ?
C007 O001 1.369(9) . ?
C008 N004 1.293(10) . ?
N004 N005 1.387(9) . ?

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
C00H C00A C00F 118.6(7) . . ?
C00H C00A C008 120.4(7) . . ?
C00F C00A C008 121.1(7) . . ?
O002 C00B O001 115.6(7) . . ?
O002 C00B C006 126.1(7) . . ?
O001 C00B C006 118.3(7) . . ?
C00O C00C C007 117.3(7) . . ?
C00O C00C C009 124.2(7) . . ?
C007 C00C C009 118.5(7) . . ?
C00J C00D C00H 120.0(8) . . ?
C007 C00E C00N 120.4(8) . . ?
C00K C00F C00A 121.2(8) . . ?
C008 C00G C00I 100.9(6) . . ?
O003 C00H C00A 122.4(7) . . ?
O003 C00H C00D 117.9(8) . . ?
C00A C00H C00D 119.6(8) . . ?
N005 C00I C006 112.2(6) . . ?
N005 C00I C00G 100.7(6) . . ?
C006 C00I C00G 110.8(7) . . ?
C00D C00J C00K 121.2(8) . . ?
C00F C00K C00J 119.3(8) . . ?
N00P C00M C00L 113.5(10) . . ?
N00P C00N C00E 123.3(10) . . ?
N00P C00N C00Q 120.0(9) . . ?
C00E C00N C00Q 116.7(8) . . ?
C00C C00O C00Q 121.7(8) . . ?
C00O C00Q C00N 120.8(8) . . ?
C2B C1A N00P 94.9(12) . . ?
C1A C2B C1B 58.1(13) . . ?
C009 C006 C00B 119.4(7) . . ?
C009 C006 C00I 125.2(7) . . ?
C00B C006 C00I 115.4(7) . . ?
C00E C007 O001 116.7(7) . . ?
C00E C007 C00C 123.1(7) . . ?
O001 C007 C00C 120.2(6) . . ?
N004 C008 C00A 121.5(7) . . ?
N004 C008 C00G 111.5(6) . . ?
C00A C008 C00G 127.0(7) . . ?
C006 C009 C00C 121.7(7) . . ?
C00N N00P C1A 124.9(11) . . ?
C00N N00P C00M 121.2(9) . . ?
C1A N00P C00M 112.8(11) . . ?
C008 N004 N005 109.4(7) . . ?
N004 N005 C00I 108.8(6) . . ?
C007 O001 C00B 121.8(6) . . ?

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
C00H C00A C00F C00K -2.1(11) . . . . ?
C008 C00A C00F C00K 178.7(7) . . . . ?
C00F C00A C00H O003 -178.6(7) . . . . ?
C008 C00A C00H O003 0.6(10) . . . . ?
C00F C00A C00H C00D 3.7(10) . . . . ?
C008 C00A C00H C00D -177.1(7) . . . . ?
C00J C00D C00H O003 179.6(7) . . . . ?
C00J C00D C00H C00A -2.6(12) . . . . ?
C008 C00G C00I N005 -26.0(7) . . . . ?
C008 C00G C00I C006 92.9(7) . . . . ?
C00H C00D C00J C00K -0.3(13) . . . . ?
C00A C00F C00K C00J -0.7(12) . . . . ?
C00D C00J C00K C00F 1.9(12) . . . . ?
C007 C00E C00N N00P 177.1(10) . . . . ?
C007 C00E C00N C00Q -1.4(14) . . . . ?
C007 C00C C00O C00Q -2.4(14) . . . . ?
C009 C00C C00O C00Q 178.0(9) . . . . ?
C00C C00O C00Q C00N 1.4(17) . . . . ?
N00P C00N C00Q C00O -178.1(11) . . . . ?
C00E C00N C00Q C00O 0.5(17) . . . . ?
N00P C1A C2B C1B 155.4(16) . . . . ?
O002 C00B C006 C009 178.3(8) . . . . ?
O001 C00B C006 C009 -0.8(11) . . . . ?
O002 C00B C006 C00I -0.4(12) . . . . ?
O001 C00B C006 C00I -179.5(6) . . . . ?
N005 C00I C006 C009 11.8(11) . . . . ?
C00G C00I C006 C009 -99.8(9) . . . . ?
N005 C00I C006 C00B -169.6(7) . . . . ?
C00G C00I C006 C00B 78.8(8) . . . . ?
C00N C00E C007 O001 -179.2(7) . . . . ?
C00N C00E C007 C00C 0.4(12) . . . . ?
C00O C00C C007 C00E 1.5(11) . . . . ?
C009 C00C C007 C00E -178.9(7) . . . . ?
C00O C00C C007 O001 -178.9(7) . . . . ?
C009 C00C C007 O001 0.7(10) . . . . ?
C00H C00A C008 N004 -0.2(10) . . . . ?
C00F C00A C008 N004 179.1(7) . . . . ?
C00H C00A C008 C00G 177.4(7) . . . . ?
C00F C00A C008 C00G -3.3(10) . . . . ?
C00I C00G C008 N004 16.4(8) . . . . ?
C00I C00G C008 C00A -161.4(6) . . . . ?
C00B C006 C009 C00C -0.6(11) . . . . ?
C00I C006 C009 C00C 177.9(7) . . . . ?
C00O C00C C009 C006 -179.7(8) . . . . ?
C007 C00C C009 C006 0.7(11) . . . . ?
C00E C00N N00P C1A -162.4(13) . . . . ?
C00Q C00N N00P C1A 16(2) . . . . ?
C00E C00N N00P C00M 4.8(18) . . . . ?
C00Q C00N N00P C00M -176.7(11) . . . . ?
C2B C1A N00P C00N -88.6(16) . . . . ?
C2B C1A N00P C00M 103.3(14) . . . . ?
C00L C00M N00P C00N 83.3(14) . . . . ?
C00L C00M N00P C1A -108.1(13) . . . . ?
C00A C008 N004 N005 179.5(6) . . . . ?
C00G C008 N004 N005 1.5(8) . . . . ?
C008 N004 N005 C00I -20.4(8) . . . . ?
C006 C00I N005 N004 -88.7(7) . . . . ?
C00G C00I N005 N004 29.2(8) . . . . ?
C00E C007 O001 C00B 177.4(7) . . . . ?
C00C C007 O001 C00B -2.2(10) . . . . ?
O002 C00B O001 C007 -176.9(7) . . . . ?
C006 C00B O001 C007 2.2(10) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.093

