# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_181127_zlw_8_97_7_0m
_database_code_depnum_ccdc_archive 'CCDC 1883891'
loop_
_audit_author_name
_audit_author_address
'Sunliang Cui'
;Zhejiang University
China
;
_audit_update_record             
;
2018-12-08 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_audit_creation_date             2018-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H12 O2 S), 0.5(H4 O2)'
_chemical_formula_sum            'C38 H26 O5 S2'
_chemical_formula_weight         626.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.6651(5)
_cell_length_b                   9.1102(3)
_cell_length_c                   18.3035(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.2240(10)
_cell_angle_gamma                90
_cell_volume                     2956.26(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      32.55
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1225 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.606
_diffrn_reflns_theta_min         2.298
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4170
_reflns_number_total             5380
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5380
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+1.2980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 S1-C10 \\sim S1A-C10A
 with sigma of 0.02
 S1-C13 \\sim S1A-C13A
 with sigma of 0.02
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 S1-C11 \\sim S1A-C11A
 with sigma of 0.04
 S1-C9 \\sim S1A-C9
 with sigma of 0.04
 S1-C12 \\sim S1A-C12A
 with sigma of 0.04
 C11-C9 \\sim C11A-C9
 with sigma of 0.04
 C11-C13 \\sim C11A-C13A
 with sigma of 0.04
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
 C10-C13 \\sim C10A-C13A
 with sigma of 0.04
3. Others
 Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=
 Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=FVAR(1)
 Fixed Sof: H3A(0.5) H3B(0.5)
4.a Free rotating group:
 O3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C4(H4), C15(H15), C19(H19), C3(H3), C2(H2), C12(H12),
 C16(H16), C17(H17), C18(H18), C13(H13), C13A(H13A), C12A(H12A), C11A(H11A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56895(10) 0.53025(18) 0.33996(7) 0.0442(3) Uani 0.666(2) 1 d D . . A 1
C11 C 0.6610(4) 0.4310(9) 0.4636(4) 0.0411(14) Uani 0.666(2) 1 d D . . A 1
H11 H 0.688314 0.415277 0.516304 0.049 Uiso 0.666(2) 1 calc R . . A 1
O2 O 0.50874(5) 0.70123(10) 0.43015(4) 0.03267(19) Uani 1 1 d . . . . .
O1 O 0.56433(5) 0.78265(11) 0.65952(5) 0.0354(2) Uani 1 1 d . . . . .
O3 O 0.500000 0.9653(2) 0.750000 0.0632(5) Uani 1 2 d S T P . .
H3A H 0.510361 0.921070 0.712386 0.095 Uiso 0.5 1 d G . . . .
H3B H 0.480418 0.897225 0.771159 0.095 Uiso 0.5 1 d G . . . .
C8 C 0.59353(6) 0.66728(12) 0.55726(6) 0.0267(2) Uani 1 1 d . . . . .
C14 C 0.66520(6) 0.60784(13) 0.61058(6) 0.0277(2) Uani 1 1 d . . . . .
C9 C 0.57122(6) 0.63796(13) 0.48031(6) 0.0276(2) Uani 1 1 d D . . . .
C7 C 0.54706(6) 0.75934(12) 0.58952(6) 0.0272(2) Uani 1 1 d . . . . .
C5 C 0.46469(6) 0.79393(13) 0.45645(6) 0.0288(2) Uani 1 1 d . . . . .
C6 C 0.47966(6) 0.82338(12) 0.53411(6) 0.0276(2) Uani 1 1 d . . . . .
C1 C 0.43045(7) 0.91695(14) 0.55596(7) 0.0326(2) Uani 1 1 d . . . . .
H1 H 0.439380 0.939073 0.608786 0.039 Uiso 1 1 calc R . . . .
C4 C 0.40342(7) 0.85591(14) 0.40022(7) 0.0344(3) Uani 1 1 d . . . . .
H4 H 0.394753 0.835470 0.347259 0.041 Uiso 1 1 calc R . . . .
C15 C 0.73457(7) 0.66608(15) 0.61156(7) 0.0344(3) Uani 1 1 d . . . . .
H15 H 0.736345 0.745645 0.578617 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6069(5) 0.5350(9) 0.4400(4) 0.0259(10) Uani 0.666(2) 1 d D . . A 1
C19 C 0.66362(8) 0.49420(15) 0.66058(7) 0.0361(3) Uani 1 1 d . . . . .
H19 H 0.616615 0.456063 0.661743 0.043 Uiso 1 1 calc R . . . .
C3 C 0.35606(7) 0.94698(15) 0.42326(8) 0.0366(3) Uani 1 1 d . . . . .
H3 H 0.314001 0.989924 0.385819 0.044 Uiso 1 1 calc R . . . .
C2 C 0.36893(7) 0.97727(15) 0.50098(8) 0.0359(3) Uani 1 1 d . . . . .
H2 H 0.335307 1.039554 0.516188 0.043 Uiso 1 1 calc R . . . .
C12 C 0.6737(5) 0.3480(11) 0.4038(5) 0.0357(11) Uani 0.666(2) 1 d D . . A 1
H12 H 0.710407 0.272448 0.411331 0.043 Uiso 0.666(2) 1 calc R . . A 1
C16 C 0.80122(7) 0.60793(18) 0.66068(8) 0.0421(3) Uani 1 1 d . . . . .
H16 H 0.848376 0.648063 0.661263 0.050 Uiso 1 1 calc R . . . .
C17 C 0.79901(8) 0.49208(18) 0.70856(8) 0.0458(4) Uani 1 1 d . . . . .
H17 H 0.844599 0.451091 0.741193 0.055 Uiso 1 1 calc R . . . .
C18 C 0.73049(9) 0.43596(17) 0.70894(8) 0.0453(3) Uani 1 1 d . . . . .
H18 H 0.728994 0.357138 0.742417 0.054 Uiso 1 1 calc R . . . .
C13 C 0.6271(6) 0.3895(14) 0.3349(6) 0.0400(12) Uani 0.666(2) 1 d D . . A 1
H13 H 0.626736 0.344685 0.287867 0.048 Uiso 0.666(2) 1 calc R . . A 1
C13A C 0.6686(11) 0.354(2) 0.3905(9) 0.041(4) Uani 0.334(2) 1 d D . . A 2
H13A H 0.701495 0.279017 0.384021 0.049 Uiso 0.334(2) 1 calc R . . A 2
C12A C 0.6122(12) 0.408(3) 0.3306(10) 0.042(3) Uani 0.334(2) 1 d D . . A 2
H12A H 0.602410 0.380961 0.278307 0.051 Uiso 0.334(2) 1 calc R . . A 2
C10A C 0.5998(10) 0.543(2) 0.4342(10) 0.032(3) Uani 0.334(2) 1 d D . . A 2
C11A C 0.5702(7) 0.5118(15) 0.3579(5) 0.048(3) Uani 0.334(2) 1 d D . . A 2
H11A H 0.525199 0.555839 0.325749 0.057 Uiso 0.334(2) 1 calc R . . A 2
S1A S 0.6766(2) 0.4274(4) 0.4771(2) 0.0353(5) Uani 0.334(2) 1 d D . . A 2


_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
S1 C10 1.745(8) . ?
S1 C13 1.702(8) . ?
C11 H11 0.9500 . ?
C11 C10 1.353(11) . ?
C11 C12 1.410(11) . ?
O2 C9 1.3659(13) . ?
O2 C5 1.3669(15) . ?
O1 C7 1.2378(13) . ?
O3 H3A 0.8700 . ?
O3 H3A 0.87(5) 2_656 ?
O3 H3B 0.8699 . ?
O3 H3B 0.87(7) 2_656 ?
C8 C14 1.4896(15) . ?
C8 C9 1.3643(15) . ?
C8 C7 1.4576(16) . ?
C14 C15 1.3942(17) . ?
C14 C19 1.3883(17) . ?
C9 C10 1.475(4) . ?
C9 C10A 1.425(10) . ?
C7 C6 1.4676(15) . ?
C5 C6 1.3863(16) . ?
C5 C4 1.3963(15) . ?
C6 C1 1.4000(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3823(17) . ?
C4 H4 0.9500 . ?
C4 C3 1.3714(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3918(17) . ?
C19 H19 0.9500 . ?
C19 C18 1.3899(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(2) . ?
C2 H2 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.344(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9500 . ?
C13 H13 0.9500 . ?
C13A H13A 0.9500 . ?
C13A C12A 1.353(12) . ?
C13A S1A 1.684(14) . ?
C12A H12A 0.9500 . ?
C12A C11A 1.414(16) . ?
C10A C11A 1.363(17) . ?
C10A S1A 1.752(17) . ?
C11A H11A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S1 C10 91.1(4) . . ?
C10 C11 H11 122.7 . . ?
C10 C11 C12 114.7(6) . . ?
C12 C11 H11 122.7 . . ?
C9 O2 C5 120.34(9) . . ?
H3A O3 H3A 124.8 . 2_656 ?
H3A O3 H3B 104.5 . . ?
H3A O3 H3B 104.5 2_656 2_656 ?
H3A O3 H3B 24.4 . 2_656 ?
H3B O3 H3A 24.4 . 2_656 ?
H3B O3 H3B 89.1 . 2_656 ?
C9 C8 C14 121.79(10) . . ?
C9 C8 C7 120.18(10) . . ?
C7 C8 C14 118.03(9) . . ?
C15 C14 C8 120.68(11) . . ?
C19 C14 C8 120.21(11) . . ?
C19 C14 C15 119.11(11) . . ?
O2 C9 C10 110.9(4) . . ?
O2 C9 C10A 105.0(8) . . ?
C8 C9 O2 122.14(10) . . ?
C8 C9 C10 127.0(4) . . ?
C8 C9 C10A 132.9(8) . . ?
O1 C7 C8 121.52(10) . . ?
O1 C7 C6 122.45(11) . . ?
C8 C7 C6 116.02(9) . . ?
O2 C5 C6 122.01(10) . . ?
O2 C5 C4 115.74(10) . . ?
C6 C5 C4 122.24(11) . . ?
C5 C6 C7 119.08(10) . . ?
C5 C6 C1 118.09(10) . . ?
C1 C6 C7 122.81(10) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.26(12) . . ?
C2 C1 H1 119.9 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.43(12) . . ?
C3 C4 H4 120.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.16(13) . . ?
C16 C15 H15 119.9 . . ?
C11 C10 S1 109.6(4) . . ?
C11 C10 C9 133.9(7) . . ?
C9 C10 S1 116.2(6) . . ?
C14 C19 H19 119.9 . . ?
C14 C19 C18 120.30(13) . . ?
C18 C19 H19 119.9 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.77(11) . . ?
C2 C3 H3 119.6 . . ?
C1 C2 C3 120.19(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C11 C12 H12 124.4 . . ?
C13 C12 C11 111.2(8) . . ?
C13 C12 H12 124.4 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.18(14) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.90(12) . . ?
C18 C17 H17 120.1 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.31(14) . . ?
C17 C18 H18 119.8 . . ?
S1 C13 H13 123.3 . . ?
C12 C13 S1 113.4(8) . . ?
C12 C13 H13 123.3 . . ?
C12A C13A H13A 122.1 . . ?
C12A C13A S1A 115.8(14) . . ?
S1A C13A H13A 122.1 . . ?
C13A C12A H12A 125.2 . . ?
C13A C12A C11A 109.6(15) . . ?
C11A C12A H12A 125.2 . . ?
C9 C10A S1A 120.4(11) . . ?
C11A C10A C9 128.8(14) . . ?
C11A C10A S1A 110.4(8) . . ?
C12A C11A H11A 123.0 . . ?
C10A C11A C12A 114.1(12) . . ?
C10A C11A H11A 123.0 . . ?
C13A S1A C10A 89.9(7) . . ?

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

data_191018_zlw_10_16_0m
_database_code_depnum_ccdc_archive 'CCDC 1960048'
loop_
_audit_author_name
_audit_author_address
'Linwei Zeng'
;zhejiang university
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_audit_creation_date             2019-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O7'
_chemical_formula_sum            'C21 H14 N2 O7'
_chemical_formula_weight         406.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.914(4)
_cell_length_b                   10.600(8)
_cell_length_c                   13.029(10)
_cell_angle_alpha                99.77(3)
_cell_angle_beta                 96.31(2)
_cell_angle_gamma                92.38(4)
_cell_volume                     933.5(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5134
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8971.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14440
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.231
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3064
_reflns_number_total             4125
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²+0.1634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1752
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H10)=Sof(O7A)=Sof(H7A)=1-FVAR(1)
 Sof(H14)=Sof(O7)=Sof(H7)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
3.b Idealised tetrahedral OH refined as rotating group:
 O7(H7), O7A(H7A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3126(4) 0.9111(2) 0.53680(16) 0.1164(8) Uani 1 1 d . . . . .
O2 O 0.1856(4) 1.03224(19) 0.43563(18) 0.1192(8) Uani 1 1 d . . . . .
O3 O 0.0780(3) 0.8606(2) 0.06666(14) 0.0959(6) Uani 1 1 d . . . . .
O4 O 0.0746(4) 0.6573(2) 0.01398(14) 0.1029(7) Uani 1 1 d . . . . .
O5 O 0.0574(3) 0.6909(2) 0.56097(13) 0.1020(7) Uani 1 1 d . . . . .
O6 O 0.33927(19) 0.60854(13) 0.53040(9) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.2295(3) 0.9281(2) 0.45439(16) 0.0776(6) Uani 1 1 d . . . . .
N2 N 0.0868(3) 0.7508(2) 0.08255(15) 0.0722(6) Uani 1 1 d . . . . .
C1 C 0.1802(3) 0.81584(19) 0.37176(15) 0.0540(5) Uani 1 1 d . . . . .
C2 C 0.1526(3) 0.8363(2) 0.26962(16) 0.0587(5) Uani 1 1 d . . . . .
H2 H 0.158307 0.918643 0.253965 0.070 Uiso 1 1 calc R . . . .
C3 C 0.1166(3) 0.7308(2) 0.19228(14) 0.0552(5) Uani 1 1 d . . . . .
C4 C 0.1083(3) 0.6084(2) 0.21235(15) 0.0590(5) Uani 1 1 d . . . . .
H4 H 0.085242 0.538577 0.157819 0.071 Uiso 1 1 calc R . . . .
C5 C 0.1350(3) 0.5907(2) 0.31564(15) 0.0562(5) Uani 1 1 d . . . . .
H5 H 0.128521 0.508096 0.330686 0.067 Uiso 1 1 calc R . . . .
C6 C 0.1712(3) 0.69404(18) 0.39655(14) 0.0489(4) Uani 1 1 d . . . . .
C7 C 0.1821(3) 0.6689(2) 0.50652(14) 0.0544(5) Uani 1 1 d . . . . .
C8 C 0.3636(3) 0.57190(18) 0.63150(13) 0.0487(4) Uani 1 1 d . . . . .
C9 C 0.4389(3) 0.68025(17) 0.71536(13) 0.0483(4) Uani 1 1 d . . . . .
C10 C 0.3273(3) 0.7319(2) 0.79254(15) 0.0588(5) Uani 1 1 d . . . . .
H10 H 0.200615 0.698574 0.792322 0.071 Uiso 0.524(4) 1 calc R . P A 2
C11 C 0.4043(4) 0.8330(2) 0.86983(18) 0.0736(7) Uani 1 1 d . . . . .
H11 H 0.328619 0.868133 0.920963 0.088 Uiso 1 1 calc R . . . .
C12 C 0.5905(4) 0.8815(2) 0.87142(19) 0.0767(7) Uani 1 1 d . . . . .
H12 H 0.641919 0.948214 0.924553 0.092 Uiso 1 1 calc R . . . .
C13 C 0.7026(4) 0.8327(2) 0.7955(2) 0.0709(6) Uani 1 1 d . . . . .
H13 H 0.829396 0.866343 0.796849 0.085 Uiso 1 1 calc R . . . .
C14 C 0.6265(3) 0.73353(18) 0.71701(17) 0.0570(5) Uani 1 1 d . . . . .
H14 H 0.701645 0.701875 0.664504 0.068 Uiso 0.476(4) 1 calc R . P A 1
C15 C 0.3336(3) 0.44802(18) 0.63046(14) 0.0501(4) Uani 1 1 d . . . . .
H15 H 0.288944 0.400532 0.564721 0.060 Uiso 1 1 calc R . . . .
C16 C 0.3580(3) 0.37187(18) 0.71421(14) 0.0486(4) Uani 1 1 d . . . . .
C17 C 0.3379(3) 0.23944(19) 0.68410(16) 0.0569(5) Uani 1 1 d . . . . .
H17 H 0.313329 0.204353 0.613166 0.068 Uiso 1 1 calc R . . . .
C18 C 0.3535(3) 0.1590(2) 0.75649(19) 0.0670(6) Uani 1 1 d . . . . .
H18 H 0.340278 0.070582 0.734462 0.080 Uiso 1 1 calc R . . . .
C19 C 0.3886(3) 0.2096(2) 0.86149(19) 0.0680(6) Uani 1 1 d . . . . .
H19 H 0.397996 0.155584 0.910872 0.082 Uiso 1 1 calc R . . . .
C20 C 0.4097(3) 0.3395(2) 0.89315(17) 0.0657(6) Uani 1 1 d . . . . .
H20 H 0.434062 0.373347 0.964327 0.079 Uiso 1 1 calc R . . . .
C21 C 0.3953(3) 0.4209(2) 0.82140(15) 0.0598(5) Uani 1 1 d . . . . .
H21 H 0.410539 0.509142 0.844356 0.072 Uiso 1 1 calc R . . . .
O7 O 0.1495(5) 0.6791(4) 0.7957(3) 0.0756(12) Uani 0.476(4) 1 d . . P A 1
H7 H 0.076554 0.691092 0.744659 0.113 Uiso 0.476(4) 1 calc GR . P A 1
O7A O 0.7304(4) 0.6832(3) 0.6424(2) 0.0674(10) Uani 0.524(4) 1 d . . P A 2
H7A H 0.840333 0.718525 0.652946 0.101 Uiso 0.524(4) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.206(3) . ?
O2 N1 1.213(3) . ?
O3 N2 1.219(3) . ?
O4 N2 1.210(3) . ?
O5 C7 1.182(2) . ?
O6 C7 1.318(2) . ?
O6 C8 1.430(2) . ?
N1 C1 1.464(3) . ?
N2 C3 1.474(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C3 C4 1.366(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C6 C7 1.496(3) . ?
C8 C9 1.478(3) . ?
C8 C15 1.318(3) . ?
C9 C10 1.388(3) . ?
C9 C14 1.389(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C10 O7 1.336(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C14 O7A 1.325(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.463(3) . ?
C16 C17 1.389(3) . ?
C16 C21 1.397(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9300 . ?
O7 H7 0.8200 . ?
O7A H7A 0.8200 . ?

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
C7 O6 C8 117.27(14) . . ?
O1 N1 O2 124.2(2) . . ?
O1 N1 C1 117.6(2) . . ?
O2 N1 C1 118.2(2) . . ?
O3 N2 C3 117.9(2) . . ?
O4 N2 O3 124.2(2) . . ?
O4 N2 C3 117.9(2) . . ?
C2 C1 N1 117.50(19) . . ?
C2 C1 C6 122.09(19) . . ?
C6 C1 N1 120.34(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 N2 118.1(2) . . ?
C2 C3 C4 122.88(19) . . ?
C4 C3 N2 118.97(19) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.49(19) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.86(19) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 123.45(18) . . ?
C5 C6 C1 118.27(18) . . ?
C5 C6 C7 118.08(18) . . ?
O5 C7 O6 124.80(19) . . ?
O5 C7 C6 123.85(18) . . ?
O6 C7 C6 111.06(15) . . ?
O6 C8 C9 112.27(16) . . ?
C15 C8 O6 114.65(16) . . ?
C15 C8 C9 132.69(17) . . ?
C10 C9 C8 122.03(18) . . ?
C10 C9 C14 118.56(19) . . ?
C14 C9 C8 119.40(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
O7 C10 C9 119.9(2) . . ?
O7 C10 C11 120.0(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
O7A C14 C9 117.6(2) . . ?
O7A C14 C13 121.6(2) . . ?
C8 C15 H15 114.2 . . ?
C8 C15 C16 131.53(17) . . ?
C16 C15 H15 114.2 . . ?
C17 C16 C15 116.83(17) . . ?
C17 C16 C21 117.50(18) . . ?
C21 C16 C15 125.65(18) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C10 O7 H7 109.5 . . ?
C14 O7A H7A 109.5 . . ?

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

data_180919_zlw_8_78_2
_database_code_depnum_ccdc_archive 'CCDC 1894582'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2020-02-05 downloaded from the CCDC.
;
_audit_creation_date             2018-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O5'
_chemical_formula_sum            'C21 H15 N O5'
_chemical_formula_weight         361.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o'
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'

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

_cell_length_a                   11.020(2)
_cell_length_b                   11.052(2)
_cell_length_c                   16.364(3)
_cell_angle_alpha                106.830(16)
_cell_angle_beta                 104.080(16)
_cell_angle_gamma                100.237(15)
_cell_volume                     1782.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2865
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2435
_cell_measurement_theta_min      1.9650
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11606
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -68.00   21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000    0.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0319213000
_diffrn_orient_matrix_UB_12      -0.0196916000
_diffrn_orient_matrix_UB_13      -0.0323563000
_diffrn_orient_matrix_UB_21      -0.0480856000
_diffrn_orient_matrix_UB_22      0.0115165000
_diffrn_orient_matrix_UB_23      -0.0322919000
_diffrn_orient_matrix_UB_31      0.0375439000
_diffrn_orient_matrix_UB_32      0.0657664000
_diffrn_orient_matrix_UB_33      0.0135867000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4355
_reflns_number_total             6500
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+0.3284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C31(H31), C32(H32), C33(H33), C34(H34), C38(H38),
 C39(H39), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17816(16) 0.60016(18) 0.65943(14) 0.0810(6) Uani 1 1 d . . . . .
O2 O 0.33084(13) 0.55422(13) 0.79641(11) 0.0550(4) Uani 1 1 d . . . . .
O3 O 0.39060(16) 0.42776(17) 0.68707(13) 0.0770(5) Uani 1 1 d . . . . .
O4 O 0.7812(2) 1.0932(2) 0.8293(2) 0.1310(10) Uani 1 1 d . . . . .
O5 O 0.9155(2) 0.9754(2) 0.82152(17) 0.1033(7) Uani 1 1 d . . . . .
N1 N 0.8063(2) 0.9884(3) 0.81597(18) 0.0850(7) Uani 1 1 d . . . . .
C1 C 0.0196(3) 0.8026(3) 0.66921(19) 0.0713(7) Uani 1 1 d . . . . .
H1 H 0.074406 0.816786 0.726118 0.086 Uiso 1 1 calc R . . . .
C2 C 0.0118(3) 0.9063(3) 0.6416(3) 0.0925(9) Uani 1 1 d . . . . .
H2 H 0.061415 0.990242 0.679365 0.111 Uiso 1 1 calc R . . . .
C3 C -0.0680(4) 0.8881(4) 0.5590(3) 0.1057(12) Uani 1 1 d . . . . .
H3 H -0.074178 0.959550 0.540634 0.127 Uiso 1 1 calc R . . . .
C4 C -0.1393(4) 0.7644(5) 0.5031(3) 0.1103(12) Uani 1 1 d . . . . .
H4 H -0.192977 0.750914 0.445924 0.132 Uiso 1 1 calc R . . . .
C5 C -0.1310(3) 0.6603(3) 0.5319(2) 0.0834(8) Uani 1 1 d . . . . .
H5 H -0.180243 0.576171 0.494181 0.100 Uiso 1 1 calc R . . . .
C6 C -0.0510(2) 0.6786(2) 0.61561(17) 0.0572(6) Uani 1 1 d . . . . .
C7 C -0.0453(2) 0.5648(3) 0.6477(2) 0.0796(8) Uani 1 1 d . . . . .
H7A H -0.103295 0.485866 0.600232 0.095 Uiso 1 1 calc R . . . .
H7B H -0.077853 0.578423 0.698737 0.095 Uiso 1 1 calc R . . . .
C8 C 0.0871(2) 0.5424(2) 0.67482(17) 0.0582(6) Uani 1 1 d . . . . .
C9 C 0.1021(2) 0.4469(2) 0.72240(16) 0.0515(5) Uani 1 1 d . . . . .
C10 C -0.0052(2) 0.3498(2) 0.71398(18) 0.0635(6) Uani 1 1 d . . . . .
H10 H -0.086788 0.344240 0.677685 0.076 Uiso 1 1 calc R . . . .
C11 C 0.0078(3) 0.2622(2) 0.7584(2) 0.0719(7) Uani 1 1 d . . . . .
H11 H -0.064410 0.197194 0.751155 0.086 Uiso 1 1 calc R . . . .
C12 C 0.1271(3) 0.2706(2) 0.81334(19) 0.0711(7) Uani 1 1 d . . . . .
H12 H 0.135305 0.211293 0.843366 0.085 Uiso 1 1 calc R . . . .
C13 C 0.2355(2) 0.3666(2) 0.82452(18) 0.0635(6) Uani 1 1 d . . . . .
H13 H 0.316311 0.373025 0.862355 0.076 Uiso 1 1 calc R . . . .
C14 C 0.2215(2) 0.45211(19) 0.77871(16) 0.0511(5) Uani 1 1 d . . . . .
C15 C 0.4057(2) 0.5325(2) 0.74257(17) 0.0541(5) Uani 1 1 d . . . . .
C16 C 0.5088(2) 0.6530(2) 0.76213(16) 0.0523(5) Uani 1 1 d . . . . .
C17 C 0.6146(2) 0.6397(2) 0.73162(18) 0.0681(7) Uani 1 1 d . . . . .
H17 H 0.619533 0.557135 0.699572 0.082 Uiso 1 1 calc R . . . .
C18 C 0.7129(2) 0.7505(3) 0.7493(2) 0.0752(8) Uani 1 1 d . . . . .
H18 H 0.785060 0.743308 0.730218 0.090 Uiso 1 1 calc R . . . .
C19 C 0.7013(2) 0.8705(2) 0.79537(19) 0.0651(7) Uani 1 1 d . . . . .
C20 C 0.5970(2) 0.8860(2) 0.82454(18) 0.0639(6) Uani 1 1 d . . . . .
H20 H 0.591205 0.969109 0.854734 0.077 Uiso 1 1 calc R . . . .
C21 C 0.5005(2) 0.7757(2) 0.80822(17) 0.0580(6) Uani 1 1 d . . . . .
H21 H 0.429389 0.784120 0.828370 0.070 Uiso 1 1 calc R . . . .
O6 O 0.65110(17) 0.33398(16) 0.75087(11) 0.0737(5) Uani 1 1 d . . . . .
O7 O 0.69089(13) 0.36618(13) 0.92358(10) 0.0504(4) Uani 1 1 d . . . . .
O8 O 0.58109(15) 0.51713(15) 0.91567(13) 0.0683(5) Uani 1 1 d . . . . .
O9 O 1.1679(2) 0.94198(19) 0.97703(17) 0.1039(7) Uani 1 1 d . . . . .
O10 O 1.21058(19) 0.77703(19) 0.89502(16) 0.0913(6) Uani 1 1 d . . . . .
N2 N 1.14420(19) 0.8246(2) 0.93713(15) 0.0634(5) Uani 1 1 d . . . . .
C22 C 0.6812(3) 0.1272(3) 0.55817(19) 0.0769(8) Uani 1 1 d . . . . .
H22 H 0.710185 0.072857 0.588130 0.092 Uiso 1 1 calc R . . . .
C23 C 0.7419(3) 0.1580(3) 0.5005(2) 0.0923(9) Uani 1 1 d . . . . .
H23 H 0.811465 0.124927 0.491774 0.111 Uiso 1 1 calc R . . . .
C24 C 0.7017(4) 0.2355(4) 0.4567(2) 0.1016(12) Uani 1 1 d . . . . .
H24 H 0.742763 0.255408 0.417020 0.122 Uiso 1 1 calc R . . . .
C25 C 0.6009(5) 0.2856(4) 0.4697(3) 0.1168(13) Uani 1 1 d . . . . .
H25 H 0.573271 0.339855 0.439251 0.140 Uiso 1 1 calc R . . . .
C26 C 0.5386(3) 0.2550(3) 0.5294(2) 0.0964(10) Uani 1 1 d . . . . .
H26 H 0.470280 0.289619 0.539227 0.116 Uiso 1 1 calc R . . . .
C27 C 0.5790(3) 0.1743(2) 0.57282(16) 0.0649(7) Uani 1 1 d . . . . .
C28 C 0.5128(3) 0.1395(3) 0.63689(17) 0.0778(8) Uani 1 1 d . . . . .
H28A H 0.421494 0.135025 0.614893 0.093 Uiso 1 1 calc R . . . .
H28B H 0.518969 0.052980 0.636697 0.093 Uiso 1 1 calc R . . . .
C29 C 0.5679(2) 0.2341(2) 0.73204(15) 0.0525(5) Uani 1 1 d . . . . .
C30 C 0.5147(2) 0.20064(19) 0.80117(15) 0.0484(5) Uani 1 1 d . . . . .
C31 C 0.4036(2) 0.0969(2) 0.77586(17) 0.0590(6) Uani 1 1 d . . . . .
H31 H 0.360688 0.049927 0.715184 0.071 Uiso 1 1 calc R . . . .
C32 C 0.3569(2) 0.0632(2) 0.83957(18) 0.0627(6) Uani 1 1 d . . . . .
H32 H 0.283050 -0.005997 0.821426 0.075 Uiso 1 1 calc R . . . .
C33 C 0.4186(2) 0.1312(2) 0.92934(18) 0.0622(6) Uani 1 1 d . . . . .
H33 H 0.387058 0.107493 0.971879 0.075 Uiso 1 1 calc R . . . .
C34 C 0.5276(2) 0.2350(2) 0.95675(16) 0.0573(6) Uani 1 1 d . . . . .
H34 H 0.568791 0.282444 1.017574 0.069 Uiso 1 1 calc R . . . .
C35 C 0.57435(19) 0.26723(19) 0.89335(15) 0.0475(5) Uani 1 1 d . . . . .
C36 C 0.6803(2) 0.4858(2) 0.92226(14) 0.0478(5) Uani 1 1 d . . . . .
C37 C 0.80606(19) 0.57244(19) 0.93160(14) 0.0459(5) Uani 1 1 d . . . . .
C38 C 0.9053(2) 0.5224(2) 0.91049(15) 0.0520(5) Uani 1 1 d . . . . .
H38 H 0.896827 0.432745 0.894556 0.062 Uiso 1 1 calc R . . . .
C39 C 1.0172(2) 0.6050(2) 0.91295(16) 0.0551(6) Uani 1 1 d . . . . .
H39 H 1.083660 0.571843 0.897730 0.066 Uiso 1 1 calc R . . . .
C40 C 1.0278(2) 0.7372(2) 0.93840(15) 0.0510(5) Uani 1 1 d . . . . .
C41 C 0.9325(2) 0.7899(2) 0.96203(19) 0.0673(7) Uani 1 1 d . . . . .
H41 H 0.943245 0.880097 0.980941 0.081 Uiso 1 1 calc R . . . .
C42 C 0.8204(2) 0.7059(2) 0.95707(18) 0.0641(7) Uani 1 1 d . . . . .
H42 H 0.753439 0.739552 0.971061 0.077 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.211(3) . ?
O2 C14 1.402(2) . ?
O2 C15 1.348(3) . ?
O3 C15 1.201(3) . ?
O4 N1 1.209(3) . ?
O5 N1 1.222(3) . ?
N1 C19 1.473(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.357(4) . ?
C1 C6 1.358(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(3) . ?
C8 C9 1.490(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.392(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C15 C16 1.485(3) . ?
C16 C17 1.390(3) . ?
C16 C21 1.380(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(4) . ?
C19 C20 1.367(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9300 . ?
O6 C29 1.208(2) . ?
O7 C35 1.403(2) . ?
O7 C36 1.354(2) . ?
O8 C36 1.194(2) . ?
O9 N2 1.218(3) . ?
O10 N2 1.208(3) . ?
N2 C40 1.471(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(4) . ?
C22 C27 1.366(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.334(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.361(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.405(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.360(4) . ?
C27 C28 1.512(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.502(3) . ?
C29 C30 1.499(3) . ?
C30 C31 1.402(3) . ?
C30 C35 1.397(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.381(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.371(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.382(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.370(3) . ?
C36 C37 1.484(3) . ?
C37 C38 1.382(3) . ?
C37 C42 1.380(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.381(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.373(3) . ?
C40 C41 1.370(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.376(3) . ?
C42 H42 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C14 117.14(17) . . ?
O4 N1 O5 123.4(2) . . ?
O4 N1 C19 118.6(2) . . ?
O5 N1 C19 117.9(2) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C6 121.4(3) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 121.2(2) . . ?
C5 C6 C7 120.6(2) . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C6 C7 C8 115.4(2) . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
O1 C8 C7 121.6(2) . . ?
O1 C8 C9 121.2(2) . . ?
C9 C8 C7 117.23(19) . . ?
C10 C9 C8 120.9(2) . . ?
C14 C9 C8 122.08(18) . . ?
C14 C9 C10 117.00(19) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 O2 119.87(18) . . ?
C13 C14 O2 117.5(2) . . ?
C13 C14 C9 122.41(19) . . ?
O2 C15 C16 111.4(2) . . ?
O3 C15 O2 123.4(2) . . ?
O3 C15 C16 125.2(2) . . ?
C17 C16 C15 118.3(2) . . ?
C21 C16 C15 121.6(2) . . ?
C21 C16 C17 120.2(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 N1 118.9(2) . . ?
C20 C19 N1 118.2(2) . . ?
C20 C19 C18 122.8(2) . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.5(2) . . ?
C21 C20 H20 120.7 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C36 O7 C35 116.40(15) . . ?
O9 N2 C40 118.6(2) . . ?
O10 N2 O9 122.9(2) . . ?
O10 N2 C40 118.5(2) . . ?
C23 C22 H22 119.3 . . ?
C23 C22 C27 121.5(3) . . ?
C27 C22 H22 119.3 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.7(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C28 120.9(3) . . ?
C26 C27 C22 118.7(3) . . ?
C26 C27 C28 120.4(3) . . ?
C27 C28 H28A 108.6 . . ?
C27 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 C27 114.52(19) . . ?
C29 C28 H28A 108.6 . . ?
C29 C28 H28B 108.6 . . ?
O6 C29 C28 120.3(2) . . ?
O6 C29 C30 121.9(2) . . ?
C30 C29 C28 117.71(18) . . ?
C31 C30 C29 121.0(2) . . ?
C35 C30 C29 122.44(18) . . ?
C35 C30 C31 116.53(19) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.4(2) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.1(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.4 . . ?
C35 C34 C33 119.3(2) . . ?
C35 C34 H34 120.4 . . ?
C30 C35 O7 119.53(18) . . ?
C34 C35 O7 117.8(2) . . ?
C34 C35 C30 122.59(19) . . ?
O7 C36 C37 112.05(18) . . ?
O8 C36 O7 123.26(18) . . ?
O8 C36 C37 124.69(19) . . ?
C38 C37 C36 121.80(18) . . ?
C42 C37 C36 118.51(19) . . ?
C42 C37 C38 119.58(19) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.3(2) . . ?
C39 C38 H38 119.8 . . ?
C38 C39 H39 120.8 . . ?
C40 C39 C38 118.4(2) . . ?
C40 C39 H39 120.8 . . ?
C39 C40 N2 118.5(2) . . ?
C41 C40 N2 119.0(2) . . ?
C41 C40 C39 122.51(19) . . ?
C40 C41 H41 120.9 . . ?
C40 C41 C42 118.3(2) . . ?
C42 C41 H41 120.9 . . ?
C37 C42 H42 119.6 . . ?
C41 C42 C37 120.8(2) . . ?
C41 C42 H42 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
