# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1g
_database_code_depnum_ccdc_archive 'CCDC 1899120'
loop_
_audit_author_name
_audit_author_address
'Jing Sun'
;Yangzhou University
China
;
_audit_update_record             
;
2019-02-24 deposited with the CCDC.	2019-05-03 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         'C27 H27 Cl N2 O8'
_chemical_formula_sum            'C27 H27 Cl N2 O8'
_chemical_formula_weight         542.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   25.773(8)
_cell_length_b                   25.773(8)
_cell_length_c                   16.667(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11071(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8572
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             4544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42959
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5433
_reflns_number_gt                3039
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1272P)²+43.1076P] 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         5433
_refine_ls_number_parameters     358
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1610
_refine_ls_R_factor_gt           0.0934
_refine_ls_wR_factor_ref         0.2871
_refine_ls_wR_factor_gt          0.2354
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.20270(19) 0.1338(2) 0.7846(3) 0.0542(12) Uani 1 1 d . . . . .
H1 H 0.2382 0.1316 0.7756 0.065 Uiso 1 1 calc R U . . .
C2 C 0.1850(2) 0.1570(2) 0.8544(3) 0.0636(14) Uani 1 1 d . . . . .
H2 H 0.2083 0.1702 0.8919 0.076 Uiso 1 1 calc R U . . .
C3 C 0.1327(2) 0.1602(2) 0.8672(3) 0.0676(15) Uani 1 1 d . . . . .
C4 C 0.0979(2) 0.1397(3) 0.8132(4) 0.0790(18) Uani 1 1 d . . . . .
H4 H 0.0625 0.1418 0.8230 0.095 Uiso 1 1 calc R U . . .
C5 C 0.1159(2) 0.1163(3) 0.7447(4) 0.0741(16) Uani 1 1 d . . . . .
H5 H 0.0925 0.1019 0.7087 0.089 Uiso 1 1 calc R U . . .
C6 C 0.16897(18) 0.11388(18) 0.7281(3) 0.0503(12) Uani 1 1 d . . . . .
C7 C 0.18519(19) 0.09059(19) 0.6506(3) 0.0526(12) Uani 1 1 d . . . . .
C8 C 0.23393(18) 0.11044(16) 0.6086(3) 0.0447(11) Uani 1 1 d . . . . .
H8 H 0.2635 0.1058 0.6449 0.054 Uiso 1 1 calc R U . . .
C9 C 0.24618(17) 0.20446(17) 0.6536(2) 0.0419(10) Uani 1 1 d . . . . .
C10 C 0.23143(16) 0.16845(16) 0.5834(2) 0.0402(10) Uani 1 1 d . . . . .
C11 C 0.17710(16) 0.18741(16) 0.5628(2) 0.0393(10) Uani 1 1 d . . . . .
C12 C 0.14154(17) 0.17169(16) 0.5064(3) 0.0437(10) Uani 1 1 d . . . . .
H12 H 0.1493 0.1444 0.4719 0.052 Uiso 1 1 calc R U . . .
C13 C 0.09342(17) 0.19690(17) 0.5008(3) 0.0457(11) Uani 1 1 d . . . . .
C14 C 0.0547(2) 0.1809(2) 0.4376(3) 0.0654(15) Uani 1 1 d . . . . .
H14A H 0.0215 0.1959 0.4496 0.098 Uiso 1 1 calc R U . . .
H14B H 0.0517 0.1437 0.4369 0.098 Uiso 1 1 calc R U . . .
H14C H 0.0662 0.1928 0.3860 0.098 Uiso 1 1 calc R U . . .
C15 C 0.08282(18) 0.23657(17) 0.5542(3) 0.0475(11) Uani 1 1 d . . . . .
H15 H 0.0508 0.2530 0.5512 0.057 Uiso 1 1 calc R U . . .
C16 C 0.11787(17) 0.25287(16) 0.6118(3) 0.0450(11) Uani 1 1 d . . . . .
H16 H 0.1099 0.2796 0.6472 0.054 Uiso 1 1 calc R U . . .
C17 C 0.16488(16) 0.22790(16) 0.6145(2) 0.0394(10) Uani 1 1 d . . . . .
C18 C 0.24538(19) 0.08114(18) 0.5306(3) 0.0508(12) Uani 1 1 d . . . . .
H18 H 0.2135 0.0648 0.5107 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2864(3) 0.0404(3) 0.5439(5) 0.1033(11) Uani 1 1 d . U . . .
C20 C 0.3132(3) -0.0475(3) 0.5115(5) 0.1115(11) Uani 1 1 d . U . . .
H20A H 0.3206 -0.0525 0.5681 0.134 Uiso 1 1 calc R U . . .
H20B H 0.2983 -0.0790 0.4895 0.134 Uiso 1 1 calc R U . . .
C21 C 0.3573(4) -0.0320(3) 0.4692(5) 0.1212(14) Uani 1 1 d . U . . .
H21A H 0.3492 -0.0297 0.4131 0.182 Uiso 1 1 calc R U . . .
H21B H 0.3844 -0.0570 0.4770 0.182 Uiso 1 1 calc R U . . .
H21C H 0.3685 0.0013 0.4883 0.182 Uiso 1 1 calc R U . . .
C22 C 0.27052(17) 0.16956(17) 0.5098(3) 0.0436(10) Uani 1 1 d . . . . .
C23 C 0.25599(19) 0.2137(2) 0.4543(3) 0.0557(13) Uani 1 1 d . . . . .
C24 C 0.2200(7) 0.2441(6) 0.3360(9) 0.127(7) Uani 0.549(14) 1 d . . P A 1
H24A H 0.2056 0.2713 0.3683 0.191 Uiso 0.549(14) 1 calc R U P A 1
H24B H 0.1942 0.2314 0.2995 0.191 Uiso 0.549(14) 1 calc R U P A 1
H24C H 0.2491 0.2572 0.3062 0.191 Uiso 0.549(14) 1 calc R U P A 1
C24' C 0.2513(7) 0.3004(6) 0.4323(11) 0.107(7) Uani 0.451(14) 1 d . . P A 2
H24D H 0.2558 0.2904 0.3772 0.160 Uiso 0.451(14) 1 calc R U P A 2
H24E H 0.2745 0.3285 0.4446 0.160 Uiso 0.451(14) 1 calc R U P A 2
H24F H 0.2162 0.3114 0.4407 0.160 Uiso 0.451(14) 1 calc R U P A 2
C25 C 0.32733(17) 0.1757(2) 0.5371(3) 0.0497(11) Uani 1 1 d . . . . .
H25A H 0.3314 0.2088 0.5640 0.060 Uiso 1 1 calc R U . . .
H25B H 0.3358 0.1485 0.5751 0.060 Uiso 1 1 calc R U . . .
C26 C 0.3638(2) 0.1730(2) 0.4679(3) 0.0641(14) Uani 1 1 d . . . . .
C27 C 0.4473(3) 0.1469(6) 0.4269(5) 0.184(6) Uani 1 1 d . . . . .
H27A H 0.4345 0.1292 0.3802 0.276 Uiso 1 1 calc R U . . .
H27B H 0.4770 0.1288 0.4474 0.276 Uiso 1 1 calc R U . . .
H27C H 0.4569 0.1817 0.4127 0.276 Uiso 1 1 calc R U . . .
Cl1 Cl 0.10865(8) 0.19006(8) 0.95286(10) 0.1061(7) Uani 1 1 d . . . . .
N1 N 0.20684(14) 0.23794(14) 0.6657(2) 0.0451(9) Uani 1 1 d . . . . .
H1A H 0.2074 0.2625 0.7006 0.054 Uiso 1 1 calc R U . . .
N2 N 0.26410(15) 0.11927(14) 0.4718(2) 0.0505(10) Uani 1 1 d . . . . .
H2A H 0.2703 0.1127 0.4222 0.061 Uiso 1 1 calc R U . . .
O1 O 0.15858(17) 0.05765(17) 0.6192(3) 0.0910(14) Uani 1 1 d . . . . .
O2 O 0.28645(12) 0.20225(12) 0.69251(17) 0.0514(8) Uani 1 1 d . . . . .
O3 O 0.3220(2) 0.04468(16) 0.5910(3) 0.0959(11) Uani 1 1 d . U . . .
O4 O 0.2783(2) -0.00086(18) 0.4978(3) 0.1082(11) Uani 1 1 d . U . . .
O5 O 0.23679(16) 0.20280(15) 0.3866(2) 0.0736(11) Uani 1 1 d . . . . .
O6 O 0.26213(16) 0.25928(15) 0.4809(2) 0.0730(11) Uani 1 1 d . . . . .
O7 O 0.35731(18) 0.1924(2) 0.4037(3) 0.0995(15) Uani 1 1 d . . . . .
O8 O 0.40702(17) 0.1483(2) 0.4878(3) 0.1156(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(7) . ?
C1 C2 1.386(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(8) . ?
C3 Cl1 1.737(6) . ?
C4 C5 1.372(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.485(7) . ?
C7 O1 1.210(6) . ?
C7 C8 1.526(7) . ?
C8 C18 1.532(6) . ?
C8 C10 1.554(6) . ?
C8 H8 0.9800 . ?
C9 O2 1.225(5) . ?
C9 N1 1.347(6) . ?
C9 C10 1.541(6) . ?
C10 C11 1.522(6) . ?
C10 C22 1.587(6) . ?
C11 C12 1.374(6) . ?
C11 C17 1.390(6) . ?
C12 C13 1.403(6) . ?
C12 H12 0.9300 . ?
C13 C15 1.382(6) . ?
C13 C14 1.510(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(6) . ?
C16 H16 0.9300 . ?
C17 N1 1.402(5) . ?
C18 N2 1.469(6) . ?
C18 C19 1.507(8) . ?
C18 H18 0.9800 . ?
C19 O3 1.212(8) . ?
C19 O4 1.329(8) . ?
C20 C21 1.395(11) . ?
C20 O4 1.519(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N2 1.452(5) . ?
C22 C23 1.513(7) . ?
C22 C25 1.541(6) . ?
C23 O5 1.263(6) . ?
C23 O6 1.266(6) . ?
C24 O5 1.424(13) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24' O6 1.364(14) . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C25 C26 1.488(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O7 1.193(6) . ?
C26 O8 1.327(7) . ?
C27 O8 1.452(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1A 0.8600 . ?
N2 H2A 0.8600 . ?

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
C6 C1 C2 121.8(5) . . ?
C6 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.2(5) . . ?
C2 C3 Cl1 120.3(5) . . ?
C4 C3 Cl1 118.4(5) . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.7(5) . . ?
C1 C6 C7 124.5(4) . . ?
C5 C6 C7 117.8(5) . . ?
O1 C7 C6 120.0(5) . . ?
O1 C7 C8 120.3(5) . . ?
C6 C7 C8 119.7(4) . . ?
C7 C8 C18 112.5(4) . . ?
C7 C8 C10 114.3(4) . . ?
C18 C8 C10 104.7(3) . . ?
C7 C8 H8 108.4 . . ?
C18 C8 H8 108.4 . . ?
C10 C8 H8 108.4 . . ?
O2 C9 N1 126.0(4) . . ?
O2 C9 C10 125.7(4) . . ?
N1 C9 C10 108.3(4) . . ?
C11 C10 C9 101.8(3) . . ?
C11 C10 C8 114.1(3) . . ?
C9 C10 C8 111.4(3) . . ?
C11 C10 C22 113.8(3) . . ?
C9 C10 C22 114.8(3) . . ?
C8 C10 C22 101.5(3) . . ?
C12 C11 C17 119.7(4) . . ?
C12 C11 C10 132.3(4) . . ?
C17 C11 C10 108.0(3) . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C15 C13 C12 118.4(4) . . ?
C15 C13 C14 121.4(4) . . ?
C12 C13 C14 120.2(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 122.8(4) . . ?
C13 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C16 C15 117.2(4) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C11 122.1(4) . . ?
C16 C17 N1 127.9(4) . . ?
C11 C17 N1 110.0(4) . . ?
N2 C18 C19 109.5(5) . . ?
N2 C18 C8 107.4(3) . . ?
C19 C18 C8 110.7(4) . . ?
N2 C18 H18 109.7 . . ?
C19 C18 H18 109.7 . . ?
C8 C18 H18 109.7 . . ?
O3 C19 O4 124.5(6) . . ?
O3 C19 C18 124.3(6) . . ?
O4 C19 C18 111.2(6) . . ?
C21 C20 O4 100.4(7) . . ?
C21 C20 H20A 111.7 . . ?
O4 C20 H20A 111.7 . . ?
C21 C20 H20B 111.7 . . ?
O4 C20 H20B 111.7 . . ?
H20A C20 H20B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 112.1(4) . . ?
N2 C22 C25 109.2(4) . . ?
C23 C22 C25 109.7(4) . . ?
N2 C22 C10 104.4(3) . . ?
C23 C22 C10 109.2(4) . . ?
C25 C22 C10 112.1(3) . . ?
O5 C23 O6 124.6(5) . . ?
O5 C23 C22 118.4(5) . . ?
O6 C23 C22 116.9(4) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C24' H24D 109.5 . . ?
O6 C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
O6 C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C26 C25 C22 111.5(4) . . ?
C26 C25 H25A 109.3 . . ?
C22 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C22 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
O7 C26 O8 122.9(5) . . ?
O7 C26 C25 126.0(5) . . ?
O8 C26 C25 111.1(5) . . ?
O8 C27 H27A 109.5 . . ?
O8 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O8 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C9 N1 C17 111.8(3) . . ?
C9 N1 H1A 124.1 . . ?
C17 N1 H1A 124.1 . . ?
C22 N2 C18 110.1(3) . . ?
C22 N2 H2A 124.9 . . ?
C18 N2 H2A 124.9 . . ?
C19 O4 C20 116.9(6) . . ?
C23 O5 C24 118.8(8) . . ?
C23 O6 C24' 119.2(9) . . ?
C26 O8 C27 115.9(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
C6 C1 C2 C3 -0.1(8) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C1 C2 C3 Cl1 -178.7(4) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
Cl1 C3 C4 C5 179.4(5) . . . . ?
C3 C4 C5 C6 -1.4(9) . . . . ?
C2 C1 C6 C5 -2.0(7) . . . . ?
C2 C1 C6 C7 177.3(5) . . . . ?
C4 C5 C6 C1 2.7(8) . . . . ?
C4 C5 C6 C7 -176.6(5) . . . . ?
C1 C6 C7 O1 151.9(5) . . . . ?
C5 C6 C7 O1 -28.9(7) . . . . ?
C1 C6 C7 C8 -31.4(7) . . . . ?
C5 C6 C7 C8 147.8(5) . . . . ?
O1 C7 C8 C18 -4.6(6) . . . . ?
C6 C7 C8 C18 178.6(4) . . . . ?
O1 C7 C8 C10 114.6(5) . . . . ?
C6 C7 C8 C10 -62.2(5) . . . . ?
O2 C9 C10 C11 176.9(4) . . . . ?
N1 C9 C10 C11 -1.9(4) . . . . ?
O2 C9 C10 C8 54.9(6) . . . . ?
N1 C9 C10 C8 -123.9(4) . . . . ?
O2 C9 C10 C22 -59.7(6) . . . . ?
N1 C9 C10 C22 121.5(4) . . . . ?
C7 C8 C10 C11 -30.9(5) . . . . ?
C18 C8 C10 C11 92.6(4) . . . . ?
C7 C8 C10 C9 83.7(4) . . . . ?
C18 C8 C10 C9 -152.8(4) . . . . ?
C7 C8 C10 C22 -153.7(3) . . . . ?
C18 C8 C10 C22 -30.2(4) . . . . ?
C9 C10 C11 C12 -179.2(5) . . . . ?
C8 C10 C11 C12 -59.2(6) . . . . ?
C22 C10 C11 C12 56.7(6) . . . . ?
C9 C10 C11 C17 0.2(4) . . . . ?
C8 C10 C11 C17 120.3(4) . . . . ?
C22 C10 C11 C17 -123.9(4) . . . . ?
C17 C11 C12 C13 0.6(6) . . . . ?
C10 C11 C12 C13 -180.0(4) . . . . ?
C11 C12 C13 C15 -1.3(6) . . . . ?
C11 C12 C13 C14 178.3(4) . . . . ?
C12 C13 C15 C16 1.0(7) . . . . ?
C14 C13 C15 C16 -178.7(4) . . . . ?
C13 C15 C16 C17 0.1(7) . . . . ?
C15 C16 C17 C11 -0.9(6) . . . . ?
C15 C16 C17 N1 178.5(4) . . . . ?
C12 C11 C17 C16 0.5(6) . . . . ?
C10 C11 C17 C16 -179.0(4) . . . . ?
C12 C11 C17 N1 -179.0(4) . . . . ?
C10 C11 C17 N1 1.5(5) . . . . ?
C7 C8 C18 N2 141.1(4) . . . . ?
C10 C8 C18 N2 16.4(5) . . . . ?
C7 C8 C18 C19 -99.4(6) . . . . ?
C10 C8 C18 C19 135.9(5) . . . . ?
N2 C18 C19 O3 85.1(9) . . . . ?
C8 C18 C19 O3 -33.1(10) . . . . ?
N2 C18 C19 O4 -95.2(7) . . . . ?
C8 C18 C19 O4 146.5(6) . . . . ?
C11 C10 C22 N2 -88.9(4) . . . . ?
C9 C10 C22 N2 154.3(3) . . . . ?
C8 C10 C22 N2 34.1(4) . . . . ?
C11 C10 C22 C23 31.1(5) . . . . ?
C9 C10 C22 C23 -85.6(4) . . . . ?
C8 C10 C22 C23 154.1(4) . . . . ?
C11 C10 C22 C25 153.0(4) . . . . ?
C9 C10 C22 C25 36.2(5) . . . . ?
C8 C10 C22 C25 -84.0(4) . . . . ?
N2 C22 C23 O5 5.4(6) . . . . ?
C25 C22 C23 O5 126.9(5) . . . . ?
C10 C22 C23 O5 -109.8(5) . . . . ?
N2 C22 C23 O6 -177.4(4) . . . . ?
C25 C22 C23 O6 -55.9(6) . . . . ?
C10 C22 C23 O6 67.4(5) . . . . ?
N2 C22 C25 C26 60.9(5) . . . . ?
C23 C22 C25 C26 -62.4(5) . . . . ?
C10 C22 C25 C26 176.1(4) . . . . ?
C22 C25 C26 O7 40.9(8) . . . . ?
C22 C25 C26 O8 -142.7(5) . . . . ?
O2 C9 N1 C17 -175.8(4) . . . . ?
C10 C9 N1 C17 3.0(5) . . . . ?
C16 C17 N1 C9 177.7(4) . . . . ?
C11 C17 N1 C9 -2.9(5) . . . . ?
C23 C22 N2 C18 -143.5(4) . . . . ?
C25 C22 N2 C18 94.6(4) . . . . ?
C10 C22 N2 C18 -25.5(4) . . . . ?
C19 C18 N2 C22 -114.2(5) . . . . ?
C8 C18 N2 C22 6.1(5) . . . . ?
O3 C19 O4 C20 6.2(13) . . . . ?
C18 C19 O4 C20 -173.4(6) . . . . ?
C21 C20 O4 C19 -80.5(8) . . . . ?
O6 C23 O5 C24 -0.8(11) . . . . ?
C22 C23 O5 C24 176.2(9) . . . . ?
O5 C23 O6 C24' -5.3(12) . . . . ?
C22 C23 O6 C24' 177.7(10) . . . . ?
O7 C26 O8 C27 1.3(11) . . . . ?
C25 C26 O8 C27 -175.3(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O3 0.86 2.40 2.921(6) 119.9 6_444
N1 H1A O2 0.86 2.01 2.827(4) 159.3 13_556

_refine_diff_density_max         0.883
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_1m
_database_code_depnum_ccdc_archive 'CCDC 1899122'
loop_
_audit_author_name
_audit_author_address
'Jing Sun'
;Yangzhou University
China
;
_audit_update_record             
;
2019-02-24 deposited with the CCDC.	2019-05-03 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         'C34 H33 Cl N2 O8'
_chemical_formula_sum            'C34 H33 Cl N2 O8'
_chemical_formula_weight         633.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.6495(11)
_cell_length_b                   25.655(3)
_cell_length_c                   12.0494(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.351(3)
_cell_angle_gamma                90
_cell_volume                     3189.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5853
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      20.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46761
_diffrn_reflns_av_unetI/netI     0.1703
_diffrn_reflns_av_R_equivalents  0.1596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7374
_reflns_number_gt                3070
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+1.1526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7374
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2284
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
C1 C 0.6721(4) 0.30347(14) 0.4539(3) 0.0552(10) Uani 1 1 d . . . . .
H1 H 0.7186 0.2728 0.4744 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7180(4) 0.34080(17) 0.3914(3) 0.0684(11) Uani 1 1 d . . . . .
H2 H 0.7951 0.3353 0.3701 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6492(5) 0.38600(16) 0.3611(3) 0.0714(12) Uani 1 1 d . . . . .
H3 H 0.6798 0.4114 0.3193 0.086 Uiso 1 1 calc R U . . .
C4 C 0.5361(5) 0.39360(14) 0.3923(3) 0.0681(12) Uani 1 1 d . . . . .
H4 H 0.4894 0.4242 0.3714 0.082 Uiso 1 1 calc R U . . .
C5 C 0.4906(3) 0.35664(13) 0.4540(3) 0.0526(10) Uani 1 1 d . . . . .
H5 H 0.4130 0.3623 0.4745 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5584(3) 0.31107(12) 0.4862(3) 0.0406(8) Uani 1 1 d . . . . .
C7 C 0.5100(3) 0.27281(12) 0.5602(3) 0.0482(9) Uani 1 1 d . . . . .
H7A H 0.5459 0.2821 0.6398 0.058 Uiso 1 1 calc R U . . .
H7B H 0.4165 0.2762 0.5450 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6291(3) 0.19065(12) 0.6220(3) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.6328(2) 0.13500(10) 0.5756(2) 0.0276(7) Uani 1 1 d . . . . .
C10 C 0.5383(3) 0.13902(11) 0.4589(3) 0.0290(7) Uani 1 1 d . . . . .
C11 C 0.4965(3) 0.10349(12) 0.3722(3) 0.0379(8) Uani 1 1 d . . . . .
H11 H 0.5315 0.0701 0.3790 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4016(3) 0.11726(14) 0.2740(3) 0.0446(9) Uani 1 1 d . . . . .
C13 C 0.3570(4) 0.07836(15) 0.1786(3) 0.0738(12) Uani 1 1 d . . . . .
H13A H 0.2894 0.0935 0.1195 0.111 Uiso 1 1 calc R U . . .
H13B H 0.3246 0.0478 0.2080 0.111 Uiso 1 1 calc R U . . .
H13C H 0.4286 0.0690 0.1474 0.111 Uiso 1 1 calc R U . . .
C14 C 0.3501(3) 0.16708(15) 0.2681(3) 0.0528(10) Uani 1 1 d . . . . .
H14 H 0.2858 0.1764 0.2037 0.063 Uiso 1 1 calc R U . . .
C15 C 0.3904(3) 0.20335(13) 0.3536(3) 0.0487(9) Uani 1 1 d . . . . .
H15 H 0.3548 0.2366 0.3478 0.058 Uiso 1 1 calc R U . . .
C16 C 0.4848(3) 0.18863(12) 0.4474(3) 0.0349(8) Uani 1 1 d . . . . .
C17 C 0.7726(3) 0.11716(11) 0.5776(2) 0.0311(7) Uani 1 1 d . . . . .
H17 H 0.8297 0.1264 0.6520 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8270(3) 0.14099(12) 0.4841(3) 0.0365(8) Uani 1 1 d . . . . .
C19 C 0.9148(3) 0.18729(12) 0.5101(3) 0.0373(8) Uani 1 1 d . . . . .
C20 C 0.9611(3) 0.20782(13) 0.6181(3) 0.0450(9) Uani 1 1 d . . . . .
H20 H 0.9387 0.1922 0.6802 0.054 Uiso 1 1 calc R U . . .
C21 C 1.0403(3) 0.25125(13) 0.6358(3) 0.0518(10) Uani 1 1 d . . . . .
H21 H 1.0697 0.2651 0.7089 0.062 Uiso 1 1 calc R U . . .
C22 C 1.0749(3) 0.27360(13) 0.5453(4) 0.0546(10) Uani 1 1 d . . . . .
C23 C 1.0332(4) 0.25327(15) 0.4373(4) 0.0712(12) Uani 1 1 d . . . . .
H23 H 1.0588 0.2685 0.3763 0.085 Uiso 1 1 calc R U . . .
C24 C 0.9537(3) 0.21044(14) 0.4193(3) 0.0570(10) Uani 1 1 d . . . . .
H24 H 0.9254 0.1967 0.3459 0.068 Uiso 1 1 calc R U . . .
C25 C 0.7610(3) 0.05785(11) 0.5703(3) 0.0330(8) Uani 1 1 d . . . . .
H25 H 0.7265 0.0478 0.4900 0.040 Uiso 1 1 calc R U . . .
C26 C 0.8921(3) 0.03239(13) 0.6149(3) 0.0398(8) Uani 1 1 d . . . . .
C27 C 1.0036(3) -0.04333(16) 0.6927(4) 0.0799(13) Uani 1 1 d . . . . .
H27A H 1.0266 -0.0574 0.6256 0.096 Uiso 1 1 calc R U . . .
H27B H 1.0733 -0.0207 0.7325 0.096 Uiso 1 1 calc R U . . .
C28 C 0.9863(4) -0.08517(18) 0.7670(4) 0.1043(17) Uani 1 1 d . . . . .
H28A H 0.9678 -0.0710 0.8349 0.157 Uiso 1 1 calc R U . . .
H28B H 1.0641 -0.1056 0.7876 0.157 Uiso 1 1 calc R U . . .
H28C H 0.9155 -0.1068 0.7280 0.157 Uiso 1 1 calc R U . . .
C29 C 0.5940(3) 0.09108(11) 0.6539(3) 0.0295(7) Uani 1 1 d . . . . .
C30 C 0.4486(3) 0.08033(13) 0.6149(3) 0.0347(8) Uani 1 1 d . . . . .
C31 C 0.2434(3) 0.11989(17) 0.5798(3) 0.0782(13) Uani 1 1 d . . . . .
H31A H 0.2290 0.1158 0.4984 0.117 Uiso 1 1 calc R U . . .
H31B H 0.2036 0.1516 0.5959 0.117 Uiso 1 1 calc R U . . .
H31C H 0.2063 0.0909 0.6106 0.117 Uiso 1 1 calc R U . . .
C32 C 0.6337(3) 0.10624(12) 0.7805(3) 0.0420(9) Uani 1 1 d . . . . .
H32A H 0.7259 0.1135 0.8016 0.050 Uiso 1 1 calc R U . . .
H32B H 0.5887 0.1380 0.7912 0.050 Uiso 1 1 calc R U . . .
C33 C 0.6049(4) 0.06528(13) 0.8584(3) 0.0426(9) Uani 1 1 d . . . . .
C34 C 0.6862(4) 0.02338(16) 1.0369(3) 0.0845(14) Uani 1 1 d . . . . .
H34A H 0.6319 0.0405 1.0784 0.127 Uiso 1 1 calc R U . . .
H34B H 0.7683 0.0153 1.0882 0.127 Uiso 1 1 calc R U . . .
H34C H 0.6452 -0.0082 1.0038 0.127 Uiso 1 1 calc R U . . .
Cl1 Cl 1.17098(11) 0.32899(4) 0.56598(11) 0.0932(4) Uani 1 1 d . . . . .
N1 N 0.5411(2) 0.21856(9) 0.5445(2) 0.0383(7) Uani 1 1 d . . . . .
N2 N 0.6655(2) 0.04458(9) 0.6353(2) 0.0385(7) Uani 1 1 d . . . . .
H2A H 0.6089 0.0188 0.5864 0.086(13) Uiso 1 1 d R . . . .
O1 O 0.6965(2) 0.20785(8) 0.71210(19) 0.0444(6) Uani 1 1 d . . . . .
O2 O 0.7976(2) 0.12288(9) 0.3880(2) 0.0541(7) Uani 1 1 d . . . . .
O3 O 0.9906(2) 0.05247(9) 0.6071(2) 0.0690(8) Uani 1 1 d . . . . .
O4 O 0.8838(2) -0.01376(9) 0.6581(2) 0.0589(7) Uani 1 1 d . . . . .
O5 O 0.4021(2) 0.04051(9) 0.5708(2) 0.0514(6) Uani 1 1 d . . . . .
O6 O 0.38183(19) 0.12202(8) 0.63169(18) 0.0455(6) Uani 1 1 d . . . . .
O7 O 0.5029(2) 0.04390(10) 0.8467(2) 0.0733(8) Uani 1 1 d . . . . .
O8 O 0.7060(2) 0.05729(9) 0.94702(19) 0.0555(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(4) . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 N1 1.454(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.226(3) . ?
C8 N1 1.352(4) . ?
C8 C9 1.537(4) . ?
C9 C10 1.516(4) . ?
C9 C17 1.552(4) . ?
C9 C29 1.589(4) . ?
C10 C11 1.374(4) . ?
C10 C16 1.387(4) . ?
C11 C12 1.398(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.385(4) . ?
C12 C13 1.507(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 N1 1.404(4) . ?
C17 C18 1.517(4) . ?
C17 C25 1.528(4) . ?
C17 H17 0.9800 . ?
C18 O2 1.214(3) . ?
C18 C19 1.496(4) . ?
C19 C20 1.377(4) . ?
C19 C24 1.395(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 Cl1 1.733(3) . ?
C23 C24 1.372(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.470(3) . ?
C25 C26 1.514(4) . ?
C25 H25 0.9800 . ?
C26 O3 1.193(4) . ?
C26 O4 1.305(4) . ?
C27 C28 1.438(5) . ?
C27 O4 1.455(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N2 1.462(3) . ?
C29 C30 1.528(4) . ?
C29 C32 1.528(4) . ?
C30 O5 1.200(3) . ?
C30 O6 1.327(3) . ?
C31 O6 1.452(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.491(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O7 1.194(4) . ?
C33 O8 1.332(4) . ?
C34 O8 1.445(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
N2 H2A 0.9857 . ?

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
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 122.1(3) . . ?
C5 C6 C7 119.2(3) . . ?
N1 C7 C6 115.2(3) . . ?
N1 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 N1 125.1(3) . . ?
O1 C8 C9 126.4(3) . . ?
N1 C8 C9 108.5(3) . . ?
C10 C9 C8 101.7(2) . . ?
C10 C9 C17 116.6(2) . . ?
C8 C9 C17 112.3(2) . . ?
C10 C9 C29 112.9(2) . . ?
C8 C9 C29 114.2(2) . . ?
C17 C9 C29 99.9(2) . . ?
C11 C10 C16 119.0(3) . . ?
C11 C10 C9 132.5(3) . . ?
C16 C10 C9 108.5(3) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 118.1(3) . . ?
C14 C12 C13 121.7(3) . . ?
C11 C12 C13 120.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C12 C14 H14 118.7 . . ?
C16 C15 C14 117.5(3) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C10 122.4(3) . . ?
C15 C16 N1 127.8(3) . . ?
C10 C16 N1 109.8(3) . . ?
C18 C17 C25 113.5(2) . . ?
C18 C17 C9 114.3(2) . . ?
C25 C17 C9 103.3(2) . . ?
C18 C17 H17 108.5 . . ?
C25 C17 H17 108.5 . . ?
C9 C17 H17 108.5 . . ?
O2 C18 C19 120.3(3) . . ?
O2 C18 C17 119.9(3) . . ?
C19 C18 C17 119.9(3) . . ?
C20 C19 C24 118.2(3) . . ?
C20 C19 C18 124.1(3) . . ?
C24 C19 C18 117.7(3) . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 Cl1 119.9(3) . . ?
C23 C22 Cl1 119.3(3) . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
N2 C25 C26 114.2(3) . . ?
N2 C25 C17 104.9(2) . . ?
C26 C25 C17 110.8(2) . . ?
N2 C25 H25 109.0 . . ?
C26 C25 H25 109.0 . . ?
C17 C25 H25 109.0 . . ?
O3 C26 O4 124.8(3) . . ?
O3 C26 C25 122.5(3) . . ?
O4 C26 C25 112.7(3) . . ?
C28 C27 O4 109.2(3) . . ?
C28 C27 H27A 109.8 . . ?
O4 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
O4 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 C30 109.4(2) . . ?
N2 C29 C32 109.6(2) . . ?
C30 C29 C32 111.2(2) . . ?
N2 C29 C9 105.4(2) . . ?
C30 C29 C9 109.8(2) . . ?
C32 C29 C9 111.3(2) . . ?
O5 C30 O6 125.2(3) . . ?
O5 C30 C29 124.4(3) . . ?
O6 C30 C29 110.4(3) . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C29 113.6(2) . . ?
C33 C32 H32A 108.9 . . ?
C29 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C29 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
O7 C33 O8 123.7(3) . . ?
O7 C33 C32 125.0(3) . . ?
O8 C33 C32 111.2(3) . . ?
O8 C34 H34A 109.5 . . ?
O8 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O8 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 N1 C16 111.5(2) . . ?
C8 N1 C7 123.9(3) . . ?
C16 N1 C7 124.6(3) . . ?
C29 N2 C25 110.4(2) . . ?
C29 N2 H2A 112.0 . . ?
C25 N2 H2A 103.8 . . ?
C26 O4 C27 116.5(3) . . ?
C30 O6 C31 115.4(3) . . ?
C33 O8 C34 117.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C1 C6 C7 -176.2(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 C7 176.2(3) . . . . ?
C1 C6 C7 N1 -32.7(4) . . . . ?
C5 C6 C7 N1 150.6(3) . . . . ?
O1 C8 C9 C10 -175.0(3) . . . . ?
N1 C8 C9 C10 3.0(3) . . . . ?
O1 C8 C9 C17 -49.7(4) . . . . ?
N1 C8 C9 C17 128.3(2) . . . . ?
O1 C8 C9 C29 63.1(4) . . . . ?
N1 C8 C9 C29 -118.9(3) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C17 C9 C10 C11 57.2(4) . . . . ?
C29 C9 C10 C11 -57.5(4) . . . . ?
C8 C9 C10 C16 -3.6(3) . . . . ?
C17 C9 C10 C16 -126.0(3) . . . . ?
C29 C9 C10 C16 119.2(3) . . . . ?
C16 C10 C11 C12 0.1(4) . . . . ?
C9 C10 C11 C12 176.6(3) . . . . ?
C10 C11 C12 C14 -1.1(5) . . . . ?
C10 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C14 C15 1.2(5) . . . . ?
C13 C12 C14 C15 -179.3(3) . . . . ?
C12 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C10 -0.9(5) . . . . ?
C14 C15 C16 N1 179.9(3) . . . . ?
C11 C10 C16 C15 1.0(4) . . . . ?
C9 C10 C16 C15 -176.3(3) . . . . ?
C11 C10 C16 N1 -179.8(3) . . . . ?
C9 C10 C16 N1 3.0(3) . . . . ?
C10 C9 C17 C18 41.3(3) . . . . ?
C8 C9 C17 C18 -75.5(3) . . . . ?
C29 C9 C17 C18 163.2(2) . . . . ?
C10 C9 C17 C25 -82.5(3) . . . . ?
C8 C9 C17 C25 160.8(2) . . . . ?
C29 C9 C17 C25 39.4(3) . . . . ?
C25 C17 C18 O2 37.3(4) . . . . ?
C9 C17 C18 O2 -80.8(3) . . . . ?
C25 C17 C18 C19 -143.8(3) . . . . ?
C9 C17 C18 C19 98.1(3) . . . . ?
O2 C18 C19 C20 -174.8(3) . . . . ?
C17 C18 C19 C20 6.3(4) . . . . ?
O2 C18 C19 C24 4.1(4) . . . . ?
C17 C18 C19 C24 -174.8(3) . . . . ?
C24 C19 C20 C21 2.2(5) . . . . ?
C18 C19 C20 C21 -178.9(3) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C20 C21 C22 Cl1 178.5(2) . . . . ?
C21 C22 C23 C24 1.2(6) . . . . ?
Cl1 C22 C23 C24 -177.9(3) . . . . ?
C22 C23 C24 C19 -0.1(6) . . . . ?
C20 C19 C24 C23 -1.6(5) . . . . ?
C18 C19 C24 C23 179.5(3) . . . . ?
C18 C17 C25 N2 -159.3(2) . . . . ?
C9 C17 C25 N2 -35.0(3) . . . . ?
C18 C17 C25 C26 77.1(3) . . . . ?
C9 C17 C25 C26 -158.6(2) . . . . ?
N2 C25 C26 O3 -149.1(3) . . . . ?
C17 C25 C26 O3 -31.0(4) . . . . ?
N2 C25 C26 O4 33.2(4) . . . . ?
C17 C25 C26 O4 151.3(3) . . . . ?
C10 C9 C29 N2 93.9(3) . . . . ?
C8 C9 C29 N2 -150.6(2) . . . . ?
C17 C9 C29 N2 -30.6(3) . . . . ?
C10 C9 C29 C30 -23.8(3) . . . . ?
C8 C9 C29 C30 91.7(3) . . . . ?
C17 C9 C29 C30 -148.3(2) . . . . ?
C10 C9 C29 C32 -147.3(2) . . . . ?
C8 C9 C29 C32 -31.8(3) . . . . ?
C17 C9 C29 C32 88.2(3) . . . . ?
N2 C29 C30 O5 -3.4(4) . . . . ?
C32 C29 C30 O5 -124.6(3) . . . . ?
C9 C29 C30 O5 111.8(3) . . . . ?
N2 C29 C30 O6 179.7(2) . . . . ?
C32 C29 C30 O6 58.5(3) . . . . ?
C9 C29 C30 O6 -65.1(3) . . . . ?
N2 C29 C32 C33 -61.2(3) . . . . ?
C30 C29 C32 C33 59.9(3) . . . . ?
C9 C29 C32 C33 -177.4(2) . . . . ?
C29 C32 C33 O7 -50.1(5) . . . . ?
C29 C32 C33 O8 133.2(3) . . . . ?
O1 C8 N1 C16 176.6(3) . . . . ?
C9 C8 N1 C16 -1.4(3) . . . . ?
O1 C8 N1 C7 -2.9(5) . . . . ?
C9 C8 N1 C7 179.0(3) . . . . ?
C15 C16 N1 C8 178.2(3) . . . . ?
C10 C16 N1 C8 -1.0(3) . . . . ?
C15 C16 N1 C7 -2.2(5) . . . . ?
C10 C16 N1 C7 178.6(3) . . . . ?
C6 C7 N1 C8 108.4(3) . . . . ?
C6 C7 N1 C16 -71.1(4) . . . . ?
C30 C29 N2 C25 128.0(3) . . . . ?
C32 C29 N2 C25 -109.8(3) . . . . ?
C9 C29 N2 C25 10.0(3) . . . . ?
C26 C25 N2 C29 136.9(3) . . . . ?
C17 C25 N2 C29 15.4(3) . . . . ?
O3 C26 O4 C27 -3.6(5) . . . . ?
C25 C26 O4 C27 174.1(3) . . . . ?
C28 C27 O4 C26 163.4(4) . . . . ?
O5 C30 O6 C31 -7.3(4) . . . . ?
C29 C30 O6 C31 169.6(3) . . . . ?
O7 C33 O8 C34 -4.3(5) . . . . ?
C32 C33 O8 C34 172.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.99 2.41 3.250(4) 142.8 3_656

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1s
_database_code_depnum_ccdc_archive 'CCDC 1899123'
loop_
_audit_author_name
_audit_author_address
'Jing Sun'
;Yangzhou University
China
;
_audit_update_record             
;
2019-02-24 deposited with the CCDC.	2019-05-03 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         'C29 H31 Cl N2 O9'
_chemical_formula_sum            'C29 H31 Cl N2 O9'
_chemical_formula_weight         587.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.0078(16)
_cell_length_b                   25.498(4)
_cell_length_c                   11.1280(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.121(4)
_cell_angle_gamma                90
_cell_volume                     2951.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5216
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24762
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6750
_reflns_number_gt                3425
_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)+(0.0507P)²+1.2742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6750
_refine_ls_number_parameters     374
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1677
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7386(3) 0.34895(12) 0.0542(3) 0.0475(8) Uani 1 1 d . . . . .
H1 H 0.6865 0.3257 -0.0046 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8611(3) 0.36009(14) 0.0512(3) 0.0622(9) Uani 1 1 d . . . . .
H2 H 0.8900 0.3449 -0.0105 0.075 Uiso 1 1 calc R U . . .
C3 C 0.9389(3) 0.39348(16) 0.1395(4) 0.0714(11) Uani 1 1 d . . . . .
H3 H 1.0214 0.4007 0.1389 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8947(3) 0.41614(15) 0.2287(3) 0.0715(11) Uani 1 1 d . . . . .
H4 H 0.9476 0.4389 0.2885 0.086 Uiso 1 1 calc R U . . .
C5 C 0.7725(3) 0.40550(13) 0.2308(3) 0.0569(9) Uani 1 1 d . . . . .
H5 H 0.7436 0.4212 0.2919 0.068 Uiso 1 1 calc R U . . .
C6 C 0.6932(3) 0.37192(11) 0.1432(2) 0.0374(7) Uani 1 1 d . . . . .
C7 C 0.5581(3) 0.36164(12) 0.1435(2) 0.0415(7) Uani 1 1 d . . . . .
H7A H 0.5075 0.3933 0.1175 0.050 Uiso 1 1 calc R U . . .
H7B H 0.5195 0.3346 0.0813 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5224(2) 0.37827(12) 0.3498(2) 0.0326(6) Uani 1 1 d . . . . .
C9 C 0.5270(2) 0.34620(9) 0.4691(2) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.5805(2) 0.29416(10) 0.4432(2) 0.0290(6) Uani 1 1 d . . . . .
C11 C 0.6173(2) 0.24960(10) 0.5166(2) 0.0328(6) Uani 1 1 d . . . . .
H11 H 0.6103 0.2477 0.5975 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6651(2) 0.20773(10) 0.4666(3) 0.0357(7) Uani 1 1 d . . . . .
C13 C 0.6737(3) 0.20953(11) 0.3461(3) 0.0413(7) Uani 1 1 d . . . . .
H13 H 0.7047 0.1806 0.3144 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6367(3) 0.25386(11) 0.2718(3) 0.0407(7) Uani 1 1 d . . . . .
H14 H 0.6422 0.2553 0.1902 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5917(2) 0.29567(10) 0.3219(2) 0.0313(6) Uani 1 1 d . . . . .
C16 C 0.6055(2) 0.37444(10) 0.5948(2) 0.0319(6) Uani 1 1 d . . . . .
H16 H 0.5922 0.4123 0.5828 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7490(3) 0.36330(11) 0.6354(3) 0.0411(7) Uani 1 1 d . . . . .
C18 C 0.9403(3) 0.38092(18) 0.5895(4) 0.0899(12) Uani 1 1 d . U . . .
H18A H 0.9646 0.3465 0.6266 0.108 Uiso 1 1 calc R U . . .
H18B H 0.9605 0.3825 0.5110 0.108 Uiso 1 1 calc R U . . .
C19 C 1.0127(4) 0.4204(2) 0.6761(6) 0.1398(18) Uani 1 1 d . U . . .
H19A H 0.9929 0.4543 0.6370 0.210 Uiso 1 1 calc R U . . .
H19B H 1.1029 0.4136 0.6964 0.210 Uiso 1 1 calc R U . . .
H19C H 0.9904 0.4197 0.7525 0.210 Uiso 1 1 calc R U . . .
C20 C 0.5430(3) 0.35587(10) 0.6927(2) 0.0345(7) Uani 1 1 d . . . . .
H20 H 0.6009 0.3299 0.7475 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5204(3) 0.39841(12) 0.7782(3) 0.0458(8) Uani 1 1 d . . . . .
C22 C 0.6034(4) 0.47645(13) 0.8909(3) 0.0817(12) Uani 1 1 d . U . . .
H22A H 0.5969 0.4610 0.9682 0.098 Uiso 1 1 calc R U . . .
H22B H 0.5287 0.4985 0.8534 0.098 Uiso 1 1 calc R U . . .
C23 C 0.7231(5) 0.50801(16) 0.9196(4) 0.1099(15) Uani 1 1 d . U . . .
H23A H 0.7964 0.4856 0.9544 0.165 Uiso 1 1 calc R U . . .
H23B H 0.7232 0.5348 0.9803 0.165 Uiso 1 1 calc R U . . .
H23C H 0.7271 0.5240 0.8429 0.165 Uiso 1 1 calc R U . . .
C24 C 0.3906(2) 0.34175(10) 0.4855(2) 0.0302(6) Uani 1 1 d . . . . .
C25 C 0.3167(3) 0.39418(10) 0.4476(3) 0.0348(7) Uani 1 1 d . . . . .
C26 C 0.3002(3) 0.48199(12) 0.5078(3) 0.0733(11) Uani 1 1 d . . . . .
H26A H 0.3062 0.4937 0.4280 0.110 Uiso 1 1 calc R U . . .
H26B H 0.3446 0.5062 0.5737 0.110 Uiso 1 1 calc R U . . .
H26C H 0.2114 0.4801 0.5023 0.110 Uiso 1 1 calc R U . . .
C27 C 0.3059(2) 0.29857(10) 0.4038(2) 0.0354(7) Uani 1 1 d . . . . .
H27A H 0.2935 0.3054 0.3148 0.043 Uiso 1 1 calc R U . . .
H27B H 0.3490 0.2650 0.4258 0.043 Uiso 1 1 calc R U . . .
C28 C 0.1780(3) 0.29614(11) 0.4234(3) 0.0368(7) Uani 1 1 d . . . . .
C29 C -0.0372(3) 0.26741(13) 0.3360(3) 0.0615(9) Uani 1 1 d . . . . .
H29A H -0.0353 0.2473 0.4096 0.092 Uiso 1 1 calc R U . . .
H29B H -0.0927 0.2506 0.2609 0.092 Uiso 1 1 calc R U . . .
H29C H -0.0687 0.3020 0.3425 0.092 Uiso 1 1 calc R U . . .
Cl1 Cl 0.71632(8) 0.15146(3) 0.55841(8) 0.0556(3) Uani 1 1 d . . . . .
N1 N 0.5526(2) 0.34518(9) 0.26710(19) 0.0348(5) Uani 1 1 d . . . . .
N2 N 0.4257(2) 0.32840(8) 0.61969(19) 0.0361(6) Uani 1 1 d . . . . .
H2A H 0.3684 0.3338 0.6495 0.043 Uiso 1 1 d R U . . .
O1 O 0.49682(18) 0.42457(8) 0.33247(17) 0.0461(5) Uani 1 1 d . . . . .
O2 O 0.8059(2) 0.33523(9) 0.7219(2) 0.0684(7) Uani 1 1 d . . . . .
O3 O 0.80222(19) 0.38860(9) 0.5618(2) 0.0612(6) Uani 1 1 d . U . . .
O4 O 0.4360(3) 0.39639(9) 0.8243(2) 0.0700(7) Uani 1 1 d . . . . .
O5 O 0.6099(2) 0.43535(8) 0.80163(18) 0.0570(6) Uani 1 1 d . U . . .
O6 O 0.23127(19) 0.40082(8) 0.34973(19) 0.0557(6) Uani 1 1 d . . . . .
O7 O 0.35843(18) 0.43026(7) 0.53745(17) 0.0458(5) Uani 1 1 d . . . . .
O8 O 0.15360(19) 0.31350(9) 0.5133(2) 0.0618(6) Uani 1 1 d . . . . .
O9 O 0.09172(17) 0.27086(8) 0.32852(18) 0.0508(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.378(4) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(4) . ?
C7 N1 1.458(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(3) . ?
C8 N1 1.368(3) . ?
C8 C9 1.545(4) . ?
C9 C10 1.517(3) . ?
C9 C16 1.559(3) . ?
C9 C24 1.576(4) . ?
C10 C11 1.380(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C12 Cl1 1.745(3) . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.407(3) . ?
C16 C17 1.521(4) . ?
C16 C20 1.541(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.198(3) . ?
C17 O3 1.321(3) . ?
C18 C19 1.440(6) . ?
C18 O3 1.462(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.460(3) . ?
C20 C21 1.517(4) . ?
C20 H20 0.9800 . ?
C21 O4 1.200(4) . ?
C21 O5 1.326(4) . ?
C22 O5 1.461(4) . ?
C22 C23 1.487(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 N2 1.455(3) . ?
C24 C27 1.533(3) . ?
C24 C25 1.550(4) . ?
C25 O6 1.195(3) . ?
C25 O7 1.325(3) . ?
C26 O7 1.456(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.496(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O8 1.201(3) . ?
C28 O9 1.332(3) . ?
C29 O9 1.451(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N2 H2A 0.8142 . ?

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
C6 C1 C2 120.9(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 121.1(3) . . ?
N1 C7 C6 113.3(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 126.0(2) . . ?
O1 C8 C9 126.3(2) . . ?
N1 C8 C9 107.7(2) . . ?
C10 C9 C8 101.9(2) . . ?
C10 C9 C16 116.0(2) . . ?
C8 C9 C16 112.3(2) . . ?
C10 C9 C24 113.7(2) . . ?
C8 C9 C24 111.92(19) . . ?
C16 C9 C24 101.42(19) . . ?
C11 C10 C15 119.5(2) . . ?
C11 C10 C9 131.7(2) . . ?
C15 C10 C9 108.8(2) . . ?
C10 C11 C12 118.3(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 Cl1 119.1(2) . . ?
C11 C12 Cl1 119.4(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 122.1(2) . . ?
C14 C15 N1 128.5(2) . . ?
C10 C15 N1 109.4(2) . . ?
C17 C16 C20 113.1(2) . . ?
C17 C16 C9 113.4(2) . . ?
C20 C16 C9 104.4(2) . . ?
C17 C16 H16 108.6 . . ?
C20 C16 H16 108.6 . . ?
C9 C16 H16 108.6 . . ?
O2 C17 O3 124.6(3) . . ?
O2 C17 C16 124.7(3) . . ?
O3 C17 C16 110.7(2) . . ?
C19 C18 O3 110.9(4) . . ?
C19 C18 H18A 109.5 . . ?
O3 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 113.3(2) . . ?
N2 C20 C16 105.80(19) . . ?
C21 C20 C16 115.3(2) . . ?
N2 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
C16 C20 H20 107.4 . . ?
O4 C21 O5 125.1(3) . . ?
O4 C21 C20 123.2(3) . . ?
O5 C21 C20 111.5(3) . . ?
O5 C22 C23 107.3(3) . . ?
O5 C22 H22A 110.3 . . ?
C23 C22 H22A 110.3 . . ?
O5 C22 H22B 110.3 . . ?
C23 C22 H22B 110.3 . . ?
H22A C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C27 110.2(2) . . ?
N2 C24 C25 114.9(2) . . ?
C27 C24 C25 107.2(2) . . ?
N2 C24 C9 101.11(19) . . ?
C27 C24 C9 113.6(2) . . ?
C25 C24 C9 110.0(2) . . ?
O6 C25 O7 124.4(2) . . ?
O6 C25 C24 123.8(2) . . ?
O7 C25 C24 111.8(2) . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C24 111.2(2) . . ?
C28 C27 H27A 109.4 . . ?
C24 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
C24 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
O8 C28 O9 122.9(3) . . ?
O8 C28 C27 125.7(3) . . ?
O9 C28 C27 111.4(2) . . ?
O9 C29 H29A 109.5 . . ?
O9 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O9 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 N1 C15 111.7(2) . . ?
C8 N1 C7 123.5(2) . . ?
C15 N1 C7 124.5(2) . . ?
C24 N2 C20 110.4(2) . . ?
C24 N2 H2A 113.4 . . ?
C20 N2 H2A 110.8 . . ?
C17 O3 C18 116.5(3) . . ?
C21 O5 C22 116.4(3) . . ?
C25 O7 C26 116.1(2) . . ?
C28 O9 C29 116.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.81 2.44 2.835(3) 111.1 .
N2 H2A O8 0.81 2.41 2.863(3) 116.0 .

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_1h
_database_code_depnum_ccdc_archive 'CCDC 1899121'
loop_
_audit_author_name
_audit_author_address
'Jing Sun'
;Yangzhou University
China
;
_audit_update_record             
;
2019-02-24 deposited with the CCDC.	2019-05-03 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         'C33 H32 N2 O8'
_chemical_formula_sum            'C33 H32 N2 O8'
_chemical_formula_weight         584.60

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.9465(5)
_cell_length_b                   10.2626(6)
_cell_length_c                   15.9359(8)
_cell_angle_alpha                97.8891(16)
_cell_angle_beta                 103.6113(15)
_cell_angle_gamma                110.4139(17)
_cell_volume                     1438.11(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8899
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22638
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.355
_diffrn_reflns_theta_max         27.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6592
_reflns_number_gt                4545
_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)+(0.0697P)²+0.6066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6592
_refine_ls_number_parameters     392
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.6284(2) 0.2402(2) -0.14486(13) 0.0471(5) Uani 1 1 d . . . . .
H1 H 0.6380 0.3213 -0.1669 0.057 Uiso 1 1 calc R U . . .
C2 C 0.5596(3) 0.1063(3) -0.20308(15) 0.0590(6) Uani 1 1 d . . . . .
H2 H 0.5234 0.0975 -0.2639 0.071 Uiso 1 1 calc R U . . .
C3 C 0.5449(3) -0.0136(3) -0.17071(16) 0.0589(6) Uani 1 1 d . . . . .
H3 H 0.4995 -0.1039 -0.2096 0.071 Uiso 1 1 calc R U . . .
C4 C 0.5970(3) 0.0001(2) -0.08152(17) 0.0553(6) Uani 1 1 d . . . . .
H4 H 0.5851 -0.0815 -0.0597 0.066 Uiso 1 1 calc R U . . .
C5 C 0.6675(2) 0.1340(2) -0.02288(14) 0.0464(5) Uani 1 1 d . . . . .
H5 H 0.7042 0.1419 0.0377 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6834(2) 0.2553(2) -0.05415(12) 0.0364(4) Uani 1 1 d . . . . .
C7 C 0.7654(3) 0.4048(2) 0.00453(12) 0.0472(5) Uani 1 1 d . . . . .
H7A H 0.8604 0.4484 -0.0073 0.057 Uiso 1 1 calc R U . . .
H7B H 0.7063 0.4602 -0.0122 0.057 Uiso 1 1 calc R U . . .
C8 C 0.9378(2) 0.44808(19) 0.15512(12) 0.0353(4) Uani 1 1 d . . . . .
C9 C 0.9399(2) 0.4936(2) 0.25169(11) 0.0333(4) Uani 1 1 d . . . . .
C10 C 0.7818(2) 0.4868(2) 0.23930(12) 0.0367(4) Uani 1 1 d . . . . .
C11 C 0.7127(2) 0.5212(3) 0.29929(15) 0.0503(5) Uani 1 1 d . . . . .
H11 H 0.7647 0.5546 0.3598 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5631(3) 0.5048(3) 0.26753(19) 0.0611(7) Uani 1 1 d . . . . .
H12 H 0.5147 0.5271 0.3072 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4870(3) 0.4559(3) 0.17818(19) 0.0594(7) Uani 1 1 d . . . . .
H13 H 0.3871 0.4449 0.1584 0.071 Uiso 1 1 calc R U . . .
C14 C 0.5551(2) 0.4226(2) 0.11699(16) 0.0514(6) Uani 1 1 d . . . . .
H14 H 0.5031 0.3901 0.0565 0.062 Uiso 1 1 calc R U . . .
C15 C 0.7028(2) 0.4393(2) 0.14890(13) 0.0380(4) Uani 1 1 d . . . . .
C16 C 1.0670(2) 0.6463(2) 0.29752(12) 0.0359(4) Uani 1 1 d . . . . .
H16 H 1.1481 0.6593 0.2704 0.043 Uiso 1 1 calc R U . . .
C17 C 1.0138(2) 0.7671(2) 0.28812(13) 0.0458(5) Uani 1 1 d . . . . .
C18 C 0.9480(2) 0.7842(2) 0.19818(13) 0.0396(4) Uani 1 1 d . . . . .
C19 C 0.8311(3) 0.8317(2) 0.18591(15) 0.0502(5) Uani 1 1 d . . . . .
H19 H 0.7934 0.8483 0.2327 0.060 Uiso 1 1 calc R U . . .
C20 C 0.7713(3) 0.8542(3) 0.10498(16) 0.0588(6) Uani 1 1 d . . . . .
H20 H 0.6921 0.8844 0.0967 0.071 Uiso 1 1 calc R U . . .
C21 C 0.8288(3) 0.8321(3) 0.03617(16) 0.0562(6) Uani 1 1 d . . . . .
H21 H 0.7889 0.8485 -0.0184 0.067 Uiso 1 1 calc R U . . .
C22 C 0.9445(3) 0.7861(2) 0.04754(14) 0.0498(5) Uani 1 1 d . . . . .
H22 H 0.9832 0.7718 0.0009 0.060 Uiso 1 1 calc R U . . .
C23 C 1.0035(2) 0.7612(2) 0.12840(14) 0.0434(5) Uani 1 1 d . . . . .
H23 H 1.0809 0.7288 0.1358 0.052 Uiso 1 1 calc R U . . .
C24 C 0.9837(2) 0.3993(2) 0.31470(12) 0.0359(4) Uani 1 1 d . . . . .
C25 C 1.1045(2) 0.3545(2) 0.29023(13) 0.0394(5) Uani 1 1 d . . . . .
C26 C 1.1447(3) 0.1736(3) 0.2039(2) 0.0677(7) Uani 1 1 d . . . . .
H26A H 1.2018 0.2399 0.1757 0.102 Uiso 1 1 calc R U . . .
H26B H 1.0884 0.0821 0.1624 0.102 Uiso 1 1 calc R U . . .
H26C H 1.2121 0.1637 0.2544 0.102 Uiso 1 1 calc R U . . .
C27 C 0.8489(2) 0.2668(2) 0.31277(14) 0.0426(5) Uani 1 1 d . . . . .
H27A H 0.7738 0.2970 0.3282 0.051 Uiso 1 1 calc R U . . .
H27B H 0.8040 0.2065 0.2528 0.051 Uiso 1 1 calc R U . . .
C28 C 0.8906(2) 0.1810(2) 0.37530(13) 0.0426(5) Uani 1 1 d . . . . .
C29 C 0.7908(3) -0.0267(3) 0.42741(17) 0.0645(7) Uani 1 1 d . . . . .
H29A H 0.8678 -0.0586 0.4191 0.097 Uiso 1 1 calc R U . . .
H29B H 0.6977 -0.1081 0.4145 0.097 Uiso 1 1 calc R U . . .
H29C H 0.8197 0.0258 0.4879 0.097 Uiso 1 1 calc R U . . .
C30 C 1.1274(2) 0.6432(2) 0.39497(12) 0.0432(5) Uani 1 1 d . . . . .
H30 H 1.1020 0.7103 0.4316 0.052 Uiso 1 1 calc R U . . .
C31 C 1.2978(3) 0.6939(3) 0.42485(14) 0.0564(6) Uani 1 1 d . . . . .
C32 C 1.5128(3) 0.7043(4) 0.53681(19) 0.0873(7) Uani 1 1 d . U . . .
H32A H 1.5357 0.6425 0.5737 0.105 Uiso 1 1 calc R U . . .
H32B H 1.5566 0.6989 0.4888 0.105 Uiso 1 1 calc R U . . .
C33 C 1.5742(4) 0.8494(4) 0.5889(2) 0.1100(10) Uani 1 1 d . U . . .
H33A H 1.5487 0.9093 0.5522 0.165 Uiso 1 1 calc R U . . .
H33B H 1.6818 0.8826 0.6116 0.165 Uiso 1 1 calc R U . . .
H33C H 1.5331 0.8531 0.6375 0.165 Uiso 1 1 calc R U . . .
N1 N 0.79668(18) 0.41603(17) 0.10020(10) 0.0392(4) Uani 1 1 d . . . . .
N2 N 1.04039(18) 0.49977(18) 0.40117(10) 0.0415(4) Uani 1 1 d . . . . .
H2A H 1.0886 0.4632 0.4465 0.073(8) Uiso 1 1 d R . . . .
O1 O 1.04434(16) 0.44714(15) 0.13079(9) 0.0455(4) Uani 1 1 d . . . . .
O2 O 1.0245(3) 0.8507(2) 0.35313(11) 0.0838(7) Uani 1 1 d . . . . .
O3 O 1.23662(16) 0.42506(18) 0.31965(11) 0.0593(4) Uani 1 1 d . . . . .
O4 O 1.04275(16) 0.22632(15) 0.23290(10) 0.0478(4) Uani 1 1 d . . . . .
O5 O 1.01279(18) 0.21285(18) 0.42656(11) 0.0641(5) Uani 1 1 d . . . . .
O6 O 0.77162(17) 0.06489(16) 0.36828(10) 0.0554(4) Uani 1 1 d . . . . .
O7 O 1.37947(19) 0.7653(2) 0.38937(12) 0.0817(7) Uani 1 1 d . . . . .
O8 O 1.3457(2) 0.6570(2) 0.49977(11) 0.0787(5) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(3) . ?
C7 N1 1.462(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(2) . ?
C8 N1 1.366(2) . ?
C8 C9 1.539(2) . ?
C9 C10 1.514(3) . ?
C9 C16 1.568(3) . ?
C9 C24 1.578(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.406(3) . ?
C16 C17 1.521(3) . ?
C16 C30 1.537(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.209(2) . ?
C17 C18 1.491(3) . ?
C18 C23 1.380(3) . ?
C18 C19 1.394(3) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 N2 1.455(2) . ?
C24 C27 1.531(3) . ?
C24 C25 1.538(3) . ?
C25 O3 1.193(2) . ?
C25 O4 1.336(2) . ?
C26 O4 1.438(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.498(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O5 1.198(2) . ?
C28 O6 1.323(2) . ?
C29 O6 1.446(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 N2 1.455(3) . ?
C30 C31 1.519(3) . ?
C30 H30 0.9800 . ?
C31 O7 1.197(3) . ?
C31 O8 1.333(3) . ?
C32 C33 1.437(5) . ?
C32 O8 1.498(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N2 H2A 0.9640 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.61(18) . . ?
C5 C6 C7 123.37(17) . . ?
C1 C6 C7 117.92(18) . . ?
N1 C7 C6 115.86(17) . . ?
N1 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 125.24(17) . . ?
O1 C8 C9 126.34(17) . . ?
N1 C8 C9 108.33(16) . . ?
C10 C9 C8 102.04(14) . . ?
C10 C9 C16 114.21(15) . . ?
C8 C9 C16 110.00(14) . . ?
C10 C9 C24 113.75(15) . . ?
C8 C9 C24 114.73(15) . . ?
C16 C9 C24 102.51(14) . . ?
C11 C10 C15 119.80(18) . . ?
C11 C10 C9 131.63(17) . . ?
C15 C10 C9 108.55(16) . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.7(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 128.11(19) . . ?
C10 C15 N1 109.97(16) . . ?
C17 C16 C30 112.81(16) . . ?
C17 C16 C9 113.50(16) . . ?
C30 C16 C9 105.24(15) . . ?
C17 C16 H16 108.4 . . ?
C30 C16 H16 108.4 . . ?
C9 C16 H16 108.4 . . ?
O2 C17 C18 119.1(2) . . ?
O2 C17 C16 120.72(19) . . ?
C18 C17 C16 120.21(16) . . ?
C23 C18 C19 119.25(19) . . ?
C23 C18 C17 122.27(19) . . ?
C19 C18 C17 118.40(18) . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.3(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N2 C24 C27 109.68(15) . . ?
N2 C24 C25 112.90(15) . . ?
C27 C24 C25 110.08(16) . . ?
N2 C24 C9 100.84(15) . . ?
C27 C24 C9 113.35(15) . . ?
C25 C24 C9 109.76(14) . . ?
O3 C25 O4 124.57(19) . . ?
O3 C25 C24 124.03(19) . . ?
O4 C25 C24 111.39(16) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C24 113.00(16) . . ?
C28 C27 H27A 109.0 . . ?
C24 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C24 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
O5 C28 O6 123.8(2) . . ?
O5 C28 C27 125.65(19) . . ?
O6 C28 C27 110.52(17) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 C31 117.24(19) . . ?
N2 C30 C16 105.46(15) . . ?
C31 C30 C16 111.49(17) . . ?
N2 C30 H30 107.4 . . ?
C31 C30 H30 107.4 . . ?
C16 C30 H30 107.4 . . ?
O7 C31 O8 124.1(2) . . ?
O7 C31 C30 124.7(2) . . ?
O8 C31 C30 111.01(19) . . ?
C33 C32 O8 108.3(3) . . ?
C33 C32 H32A 110.0 . . ?
O8 C32 H32A 110.0 . . ?
C33 C32 H32B 110.0 . . ?
O8 C32 H32B 110.0 . . ?
H32A C32 H32B 108.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C8 N1 C15 111.07(15) . . ?
C8 N1 C7 122.27(17) . . ?
C15 N1 C7 123.96(17) . . ?
C30 N2 C24 110.36(15) . . ?
C30 N2 H2A 116.6 . . ?
C24 N2 H2A 110.8 . . ?
C25 O4 C26 116.56(18) . . ?
C28 O6 C29 117.63(18) . . ?
C31 O8 C32 115.81(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.96 2.36 2.954(2) 119.1 .

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.044

