# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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_190829_dhche_0ma
_database_code_depnum_ccdc_archive 'CCDC 1965984'
loop_
_audit_author_name
_audit_author_address
'Letao Huang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-08-30
_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         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.276(3)
_cell_length_b                   8.9776(9)
_cell_length_c                   9.1929(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.218(5)
_cell_angle_gamma                90
_cell_volume                     1651.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.08
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1662 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.7419.
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    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12858
_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         29.172
_diffrn_reflns_theta_min         2.486
_diffrn_ambient_temperature      170.0
_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                3339
_reflns_number_total             4431
_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         0.296
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.3498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1185
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 0.85908(6) 0.64959(14) 0.03215(11) 0.0414(3) Uani 1 1 d . . . . .
O2 O 0.96393(6) 0.55393(14) 0.11747(10) 0.0395(3) Uani 1 1 d . . . . .
O3 O 0.54797(5) 0.50337(10) 0.65759(9) 0.0240(2) Uani 1 1 d . . . . .
O4 O 0.57449(5) 0.46974(10) 0.95094(9) 0.0275(2) Uani 1 1 d . . . . .
N1 N 0.70483(5) 0.55052(11) 0.41745(10) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.92173(8) 0.6144(2) -0.00871(16) 0.0389(4) Uani 1 1 d . . . . .
H1A H 0.942312 0.705134 -0.043093 0.047 Uiso 1 1 calc R . . . .
H1B H 0.915773 0.540753 -0.089935 0.047 Uiso 1 1 calc R . . . .
C2 C 0.85885(7) 0.58445(15) 0.16749(13) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.92234(7) 0.52621(15) 0.21897(14) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.93678(7) 0.45376(15) 0.34987(13) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.979943 0.413585 0.382717 0.032 Uiso 1 1 calc R . . . .
C5 C 0.88431(7) 0.44038(13) 0.43634(13) 0.0229(3) Uani 1 1 d . . . . .
C6 C 0.82002(7) 0.50169(13) 0.38450(12) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.80755(7) 0.57391(14) 0.24421(13) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.764719 0.613089 0.206301 0.030 Uiso 1 1 calc R . . . .
C8 C 0.89398(7) 0.36256(15) 0.57255(14) 0.0266(3) Uani 1 1 d . . . . .
H8 H 0.936115 0.318267 0.607255 0.032 Uiso 1 1 calc R . . . .
C9 C 0.84384(7) 0.35038(14) 0.65426(13) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.851560 0.296319 0.744222 0.031 Uiso 1 1 calc R . . . .
C10 C 0.78036(7) 0.41646(13) 0.60834(12) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.76872(6) 0.48831(13) 0.47253(12) 0.0201(2) Uani 1 1 d . . . . .
C12 C 0.65012(7) 0.47232(13) 0.47162(12) 0.0210(3) Uani 1 1 d . . . . .
H12A H 0.644581 0.372508 0.425490 0.025 Uiso 1 1 calc R . . . .
H12B H 0.608058 0.528269 0.441797 0.025 Uiso 1 1 calc R . . . .
C13 C 0.66258(7) 0.45503(12) 0.63773(12) 0.0199(2) Uani 1 1 d . . . . .
C14 C 0.72809(7) 0.41884(12) 0.70285(12) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.74115(7) 0.39552(13) 0.85492(12) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.785074 0.369683 0.900417 0.028 Uiso 1 1 calc R . . . .
C16 C 0.69102(7) 0.40945(13) 0.94078(12) 0.0233(3) Uani 1 1 d . . . . .
H16 H 0.700787 0.391909 1.043903 0.028 Uiso 1 1 calc R . . . .
C17 C 0.62683(7) 0.44882(13) 0.87674(12) 0.0215(3) Uani 1 1 d . . . . .
C18 C 0.61270(7) 0.47097(12) 0.72311(12) 0.0205(2) Uani 1 1 d . . . . .
C19 C 0.53351(8) 0.65967(15) 0.65236(15) 0.0304(3) Uani 1 1 d . . . . .
H19A H 0.488362 0.676037 0.598370 0.046 Uiso 1 1 calc GR . . . .
H19B H 0.565955 0.711688 0.602213 0.046 Uiso 1 1 calc GR . . . .
H19C H 0.536331 0.698205 0.752905 0.046 Uiso 1 1 calc GR . . . .
C20 C 0.58739(8) 0.44948(16) 1.10763(13) 0.0303(3) Uani 1 1 d . . . . .
H20A H 0.599729 0.345504 1.130249 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.547162 0.474222 1.149170 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.624112 0.514850 1.150573 0.045 Uiso 1 1 calc GR . . . .
C21 C 0.70129(7) 0.71220(13) 0.43914(15) 0.0278(3) Uani 1 1 d . . . . .
H21A H 0.660638 0.751360 0.379267 0.042 Uiso 1 1 calc GR . . . .
H21B H 0.740505 0.759794 0.409249 0.042 Uiso 1 1 calc GR . . . .
H21C H 0.700349 0.733358 0.543370 0.042 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4169(19) . ?
O1 C2 1.3755(15) . ?
O2 C1 1.4331(18) . ?
O2 C3 1.3768(16) . ?
O3 C18 1.3845(16) . ?
O3 C19 1.4327(15) . ?
O4 C17 1.3635(16) . ?
O4 C20 1.4338(14) . ?
N1 C11 1.4270(16) . ?
N1 C12 1.4656(16) . ?
N1 C21 1.4685(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.400(2) . ?
C2 C7 1.3502(19) . ?
C3 C4 1.3580(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.4314(19) . ?
C5 C6 1.4250(18) . ?
C5 C8 1.4198(17) . ?
C6 C7 1.4294(16) . ?
C6 C11 1.4216(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.3618(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.4188(18) . ?
C10 C11 1.3915(16) . ?
C10 C14 1.4742(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5152(15) . ?
C13 C14 1.4048(18) . ?
C13 C18 1.3834(17) . ?
C14 C15 1.3963(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3889(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3857(19) . ?
C17 C18 1.4094(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 O1 C1 106.15(11) . . ?
C3 O2 C1 105.43(11) . . ?
C18 O3 C19 113.27(10) . . ?
C17 O4 C20 116.98(10) . . ?
C11 N1 C12 112.67(9) . . ?
C11 N1 C21 113.58(10) . . ?
C12 N1 C21 111.79(10) . . ?
O1 C1 O2 108.31(11) . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O2 C1 H1A 110.0 . . ?
O2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O1 C2 C3 109.17(12) . . ?
C7 C2 O1 128.08(13) . . ?
C7 C2 C3 122.75(12) . . ?
O2 C3 C2 109.47(11) . . ?
C4 C3 O2 128.22(13) . . ?
C4 C3 C2 122.31(13) . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.29(13) . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 120.22(11) . . ?
C8 C5 C4 121.41(12) . . ?
C8 C5 C6 118.34(12) . . ?
C5 C6 C7 119.80(12) . . ?
C11 C6 C5 119.38(10) . . ?
C11 C6 C7 120.81(12) . . ?
C2 C7 C6 117.61(12) . . ?
C2 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
C5 C8 H8 119.5 . . ?
C9 C8 C5 121.08(12) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.61(11) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C14 122.29(10) . . ?
C11 C10 C9 118.44(12) . . ?
C11 C10 C14 119.17(11) . . ?
C6 C11 N1 118.06(10) . . ?
C10 C11 N1 120.91(11) . . ?
C10 C11 C6 121.04(11) . . ?
N1 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
N1 C12 C13 112.24(10) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C14 C13 C12 116.53(11) . . ?
C18 C13 C12 122.84(11) . . ?
C18 C13 C14 120.62(10) . . ?
C13 C14 C10 118.17(10) . . ?
C15 C14 C10 123.29(12) . . ?
C15 C14 C13 118.43(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.12(12) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.30(11) . . ?
C17 C16 H16 119.8 . . ?
O4 C17 C16 125.17(10) . . ?
O4 C17 C18 115.62(11) . . ?
C16 C17 C18 119.21(12) . . ?
O3 C18 C17 119.47(11) . . ?
C13 C18 O3 120.21(10) . . ?
C13 C18 C17 120.28(11) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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_191012_che_0m
_database_code_depnum_ccdc_archive 'CCDC 1965994'
loop_
_audit_author_name
_audit_author_address
'Letao Huang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-10-14
_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         'Cl, C21 H18 N O4, C H4 O'
_chemical_formula_sum            'C22 H22 Cl N O5'
_chemical_formula_weight         415.85
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.288(6)
_cell_length_b                   8.182(3)
_cell_length_c                   17.804(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.917(14)
_cell_angle_gamma                90
_cell_volume                     1921.7(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7032
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0701 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
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    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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                3545
_reflns_number_total             4215
_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         0.282
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.037
_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)+(0.0462P)²+0.7795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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
Cl1 Cl 0.65404(3) 0.01266(5) 0.30490(2) 0.03013(11) Uani 1 1 d . . . . .
O1 O 0.13867(9) -0.08002(15) 0.33923(6) 0.0350(3) Uani 1 1 d . . . . .
O2 O 0.27038(8) 0.08829(14) 0.26108(6) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.88599(8) 0.59433(16) 0.46582(6) 0.0370(3) Uani 1 1 d . . . . .
O4 O 0.89343(9) 0.62710(16) 0.59536(6) 0.0373(3) Uani 1 1 d . . . . .
N1 N 0.51878(9) 0.32110(15) 0.36972(6) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.32536(11) 0.06075(19) 0.49669(8) 0.0263(3) Uani 1 1 d . . . . .
H1 H 0.337285 0.054634 0.550308 0.032 Uiso 1 1 calc R . . . .
C2 C 0.24134(12) -0.01383(19) 0.45900(9) 0.0278(3) Uani 1 1 d . . . . .
H2 H 0.196676 -0.071953 0.487215 0.033 Uiso 1 1 calc R . . . .
C3 C 0.21971(11) -0.00640(18) 0.37972(9) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.28471(11) 0.07848(18) 0.33852(8) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.37223(11) 0.15365(17) 0.37693(8) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.39389(11) 0.14603(17) 0.45675(8) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.48330(11) 0.22798(18) 0.49197(8) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.54958(11) 0.31115(17) 0.44856(7) 0.0213(3) Uani 1 1 d . . . . .
C9 C 0.43680(11) 0.24588(18) 0.33705(8) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.420991 0.254982 0.283737 0.027 Uiso 1 1 calc R . . . .
C10 C 0.50450(11) 0.22816(18) 0.57245(8) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.462036 0.168146 0.601750 0.030 Uiso 1 1 calc R . . . .
C11 C 0.58406(12) 0.31239(19) 0.60764(8) 0.0259(3) Uani 1 1 d . . . . .
H11 H 0.593716 0.316941 0.661338 0.031 Uiso 1 1 calc R . . . .
C12 C 0.65342(11) 0.39409(18) 0.56604(8) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.64195(11) 0.38613(18) 0.48489(8) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.72364(11) 0.4488(2) 0.44770(8) 0.0275(3) Uani 1 1 d . . . . .
H14 H 0.724224 0.435190 0.394766 0.033 Uiso 1 1 calc R . . . .
C15 C 0.80036(11) 0.5282(2) 0.49030(9) 0.0282(3) Uani 1 1 d . . . . .
C16 C 0.80594(12) 0.5459(2) 0.56860(9) 0.0283(3) Uani 1 1 d . . . . .
C17 C 0.73630(12) 0.47692(19) 0.60812(8) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.742319 0.483301 0.661749 0.033 Uiso 1 1 calc R . . . .
C18 C 0.93408(13) 0.6853(2) 0.52915(10) 0.0360(4) Uani 1 1 d . . . . .
H18A H 0.920076 0.803467 0.521982 0.043 Uiso 1 1 calc R . . . .
H18B H 1.008371 0.668472 0.534371 0.043 Uiso 1 1 calc R . . . .
C19 C 0.06612(13) -0.1602(2) 0.37964(10) 0.0380(4) Uani 1 1 d . . . . .
H19A H 0.013827 -0.211054 0.343608 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.034634 -0.080012 0.410402 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.100176 -0.244405 0.412616 0.057 Uiso 1 1 calc GR . . . .
C20 C 0.17882(13) 0.1702(2) 0.22890(9) 0.0349(4) Uani 1 1 d . . . . .
H20A H 0.187953 0.212062 0.178592 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.164297 0.261304 0.261671 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.122148 0.092790 0.224615 0.052 Uiso 1 1 calc GR . . . .
C21 C 0.57269(12) 0.4198(2) 0.31706(8) 0.0271(3) Uani 1 1 d . . . . .
H21A H 0.632283 0.359619 0.304660 0.041 Uiso 1 1 calc GR . . . .
H21B H 0.594252 0.523773 0.341170 0.041 Uiso 1 1 calc GR . . . .
H21C H 0.527116 0.441123 0.270620 0.041 Uiso 1 1 calc GR . . . .
O5 O 0.86806(10) 0.1149(2) 0.38053(7) 0.0508(4) Uani 1 1 d . . . . .
H5 H 0.809347 0.076040 0.371311 0.076 Uiso 1 1 calc GR . . . .
C22 C 0.89855(17) 0.1795(3) 0.31386(12) 0.0618(6) Uani 1 1 d . . . . .
H22A H 0.899014 0.092481 0.276075 0.093 Uiso 1 1 calc GR . . . .
H22B H 0.966798 0.225679 0.324713 0.093 Uiso 1 1 calc GR . . . .
H22C H 0.851148 0.265426 0.294237 0.093 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3621(19) . ?
O1 C19 1.430(2) . ?
O2 C4 1.3712(18) . ?
O2 C20 1.4457(19) . ?
O3 C15 1.3774(19) . ?
O3 C18 1.435(2) . ?
O4 C16 1.3734(19) . ?
O4 C18 1.436(2) . ?
N1 C8 1.4163(18) . ?
N1 C9 1.3233(19) . ?
N1 C21 1.4854(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(2) . ?
C1 C6 1.406(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.408(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.417(2) . ?
C5 C9 1.399(2) . ?
C6 C7 1.441(2) . ?
C7 C8 1.414(2) . ?
C7 C10 1.427(2) . ?
C8 C13 1.453(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.351(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.418(2) . ?
C12 C13 1.436(2) . ?
C12 C17 1.426(2) . ?
C13 C14 1.433(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.360(2) . ?
C15 C16 1.395(2) . ?
C16 C17 1.352(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C22 1.403(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C3 O1 C19 118.33(13) . . ?
C4 O2 C20 115.72(11) . . ?
C15 O3 C18 105.17(12) . . ?
C16 O4 C18 105.18(12) . . ?
C8 N1 C21 123.57(12) . . ?
C9 N1 C8 122.23(12) . . ?
C9 N1 C21 114.17(12) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.72(14) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.75(14) . . ?
C3 C2 H2 119.1 . . ?
O1 C3 C2 124.37(14) . . ?
O1 C3 C4 116.43(13) . . ?
C4 C3 C2 119.19(14) . . ?
O2 C4 C3 122.81(14) . . ?
O2 C4 C5 117.81(13) . . ?
C3 C4 C5 119.34(13) . . ?
C4 C5 C6 121.39(13) . . ?
C9 C5 C4 120.48(13) . . ?
C9 C5 C6 118.03(13) . . ?
C1 C6 C5 117.60(13) . . ?
C1 C6 C7 124.14(13) . . ?
C5 C6 C7 118.25(13) . . ?
C8 C7 C6 121.43(12) . . ?
C8 C7 C10 119.19(13) . . ?
C10 C7 C6 119.37(13) . . ?
N1 C8 C13 123.02(12) . . ?
C7 C8 N1 116.39(13) . . ?
C7 C8 C13 120.55(12) . . ?
N1 C9 C5 123.40(13) . . ?
N1 C9 H9 118.3 . . ?
C5 C9 H9 118.3 . . ?
C7 C10 H10 119.5 . . ?
C11 C10 C7 121.00(14) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.33(13) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 120.49(14) . . ?
C11 C12 C17 117.33(13) . . ?
C17 C12 C13 122.12(14) . . ?
C12 C13 C8 116.67(13) . . ?
C14 C13 C8 126.30(13) . . ?
C14 C13 C12 117.01(13) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.16(14) . . ?
C15 C14 H14 120.9 . . ?
O3 C15 C16 109.21(14) . . ?
C14 C15 O3 127.11(14) . . ?
C14 C15 C16 123.58(15) . . ?
O4 C16 C15 109.76(14) . . ?
C17 C16 O4 128.71(14) . . ?
C17 C16 C15 121.29(15) . . ?
C12 C17 H17 121.3 . . ?
C16 C17 C12 117.31(14) . . ?
C16 C17 H17 121.3 . . ?
O3 C18 O4 107.29(13) . . ?
O3 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
O4 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O5 H5 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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_190829_dhsan_0m
_database_code_depnum_ccdc_archive 'CCDC 1965989'
loop_
_audit_author_name
_audit_author_address
'Letao Huang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-11-15 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2019-08-30
_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         'C20 H15 N O4'
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.33
_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                   9.3078(3)
_cell_length_b                   10.2556(3)
_cell_length_c                   17.4870(5)
_cell_angle_alpha                103.6680(10)
_cell_angle_beta                 100.3310(10)
_cell_angle_gamma                103.7570(10)
_cell_volume                     1525.61(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0824 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.9366.
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    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33109
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.578
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                7047
_reflns_number_total             8523
_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         0.351
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.032
_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)+(0.0614P)²+0.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C19(H19A,H19B), C21(H21A,H21B), C28(H28A,H28B),
 C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C11(H11), C12(H12), C15(H15), C18(H18), C24(H24), C25(H25),
 C31(H31), C32(H32), C35(H35), C38(H38)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C)
;
_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 0.19850(11) 0.72204(10) 0.53143(6) 0.0353(2) Uani 1 1 d . . . . .
O2 O 0.00099(11) 0.76105(10) 0.58933(6) 0.0395(2) Uani 1 1 d . . . . .
O3 O 0.77770(10) 0.09342(10) 0.59640(6) 0.0378(2) Uani 1 1 d . . . . .
O4 O 0.66136(11) -0.08062(10) 0.64691(7) 0.0418(2) Uani 1 1 d . . . . .
N1 N 0.46181(11) 0.44874(10) 0.59855(6) 0.0256(2) Uani 1 1 d . . . . .
C1 C 0.08614(14) 0.79577(13) 0.53232(8) 0.0314(3) Uani 1 1 d . . . . .
H1A H 0.016852 0.768164 0.477434 0.038 Uiso 1 1 calc R . . . .
H1B H 0.136290 0.898202 0.548663 0.038 Uiso 1 1 calc R . . . .
C2 C 0.16328(13) 0.63011(12) 0.57560(7) 0.0260(2) Uani 1 1 d . . . . .
C3 C 0.04493(13) 0.65243(12) 0.61000(7) 0.0287(2) Uani 1 1 d . . . . .
C4 C -0.01096(13) 0.57414(13) 0.65766(8) 0.0313(3) Uani 1 1 d . . . . .
H4 H -0.091916 0.589945 0.681262 0.038 Uiso 1 1 calc R . . . .
C5 C 0.05636(13) 0.47001(12) 0.67002(7) 0.0275(2) Uani 1 1 d . . . . .
H5 H 0.021061 0.414642 0.703202 0.033 Uiso 1 1 calc R . . . .
C6 C 0.17440(12) 0.44566(12) 0.63461(7) 0.0231(2) Uani 1 1 d . . . . .
C7 C 0.23065(12) 0.52845(12) 0.58619(7) 0.0243(2) Uani 1 1 d . . . . .
C8 C 0.35475(14) 0.49602(13) 0.54712(7) 0.0287(2) Uani 1 1 d . . . . .
H8A H 0.307634 0.422090 0.494549 0.034 Uiso 1 1 calc R . . . .
H8B H 0.411683 0.581151 0.535875 0.034 Uiso 1 1 calc R . . . .
C9 C 0.38258(12) 0.33535(11) 0.62419(6) 0.0224(2) Uani 1 1 d . . . . .
C10 C 0.24222(12) 0.33156(11) 0.64228(6) 0.0222(2) Uani 1 1 d . . . . .
C11 C 0.16797(12) 0.21768(12) 0.66752(7) 0.0248(2) Uani 1 1 d . . . . .
H11 H 0.070064 0.212019 0.677622 0.030 Uiso 1 1 calc R . . . .
C12 C 0.23478(13) 0.11599(12) 0.67754(7) 0.0260(2) Uani 1 1 d . . . . .
H12 H 0.184247 0.042666 0.696520 0.031 Uiso 1 1 calc R . . . .
C13 C 0.37804(13) 0.11757(12) 0.66021(7) 0.0243(2) Uani 1 1 d . . . . .
C14 C 0.45225(12) 0.22778(11) 0.63114(6) 0.0224(2) Uani 1 1 d . . . . .
C15 C 0.59127(13) 0.22658(12) 0.60737(7) 0.0261(2) Uani 1 1 d . . . . .
H15 H 0.642632 0.298775 0.587870 0.031 Uiso 1 1 calc R . . . .
C16 C 0.64635(13) 0.11747(12) 0.61398(8) 0.0283(2) Uani 1 1 d . . . . .
C17 C 0.57501(14) 0.01090(12) 0.64448(8) 0.0302(2) Uani 1 1 d . . . . .
C18 C 0.44401(14) 0.00794(12) 0.66824(8) 0.0296(2) Uani 1 1 d . . . . .
H18 H 0.397916 -0.064144 0.689377 0.036 Uiso 1 1 calc R . . . .
C19 C 0.76848(17) -0.04576(14) 0.60025(10) 0.0402(3) Uani 1 1 d . . . . .
H19A H 0.869900 -0.050465 0.626425 0.048 Uiso 1 1 calc R . . . .
H19B H 0.733868 -0.112477 0.544861 0.048 Uiso 1 1 calc R . . . .
C20 C 0.56451(14) 0.56348(13) 0.66781(9) 0.0347(3) Uani 1 1 d . . . . .
H20A H 0.504728 0.602217 0.703088 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.620400 0.637190 0.648147 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.637171 0.527854 0.698589 0.052 Uiso 1 1 calc GR . . . .
O5 O 0.15473(11) 0.68336(10) 0.96789(6) 0.0388(2) Uani 1 1 d . . . . .
O6 O -0.08642(11) 0.66776(11) 0.89507(7) 0.0410(2) Uani 1 1 d . . . . .
O7 O 0.68185(12) -0.00214(11) 0.91817(8) 0.0514(3) Uani 1 1 d . . . . .
O8 O 0.52202(13) -0.22857(11) 0.85952(8) 0.0495(3) Uani 1 1 d . . . . .
N2 N 0.36030(11) 0.34529(10) 0.91601(6) 0.02539(19) Uani 1 1 d . . . . .
C21 C 0.04431(16) 0.75790(14) 0.95922(8) 0.0338(3) Uani 1 1 d . . . . .
H21A H 0.088045 0.844808 0.945565 0.041 Uiso 1 1 calc R . . . .
H21B H 0.013668 0.784147 1.010762 0.041 Uiso 1 1 calc R . . . .
C22 C 0.08095(14) 0.54769(13) 0.92094(7) 0.0286(2) Uani 1 1 d . . . . .
C23 C -0.06343(14) 0.53739(14) 0.87782(8) 0.0309(2) Uani 1 1 d . . . . .
C24 C -0.16030(14) 0.41235(15) 0.82630(8) 0.0331(3) Uani 1 1 d . . . . .
H24 H -0.259552 0.405766 0.797189 0.040 Uiso 1 1 calc R . . . .
C25 C -0.10617(13) 0.29502(14) 0.81860(7) 0.0295(2) Uani 1 1 d . . . . .
H25 H -0.170093 0.206883 0.783144 0.035 Uiso 1 1 calc R . . . .
C26 C 0.03901(13) 0.30384(12) 0.86154(7) 0.0246(2) Uani 1 1 d . . . . .
C27 C 0.13619(13) 0.43433(12) 0.91478(7) 0.0260(2) Uani 1 1 d . . . . .
C28 C 0.28952(13) 0.43894(12) 0.96282(7) 0.0278(2) Uani 1 1 d . . . . .
H28A H 0.357995 0.536287 0.979978 0.033 Uiso 1 1 calc R . . . .
H28B H 0.277129 0.411620 1.012433 0.033 Uiso 1 1 calc R . . . .
C29 C 0.25803(12) 0.20648(11) 0.88119(7) 0.0236(2) Uani 1 1 d . . . . .
C30 C 0.10112(13) 0.18284(12) 0.85500(7) 0.0244(2) Uani 1 1 d . . . . .
C31 C 0.00576(13) 0.04306(12) 0.82073(7) 0.0280(2) Uani 1 1 d . . . . .
H31 H -0.101642 0.025896 0.804182 0.034 Uiso 1 1 calc R . . . .
C32 C 0.06524(14) -0.06806(13) 0.81094(8) 0.0307(2) Uani 1 1 d . . . . .
H32 H -0.001237 -0.160675 0.786173 0.037 Uiso 1 1 calc R . . . .
C33 C 0.22456(14) -0.04704(12) 0.83720(7) 0.0278(2) Uani 1 1 d . . . . .
C34 C 0.32284(13) 0.09237(12) 0.87363(7) 0.0258(2) Uani 1 1 d . . . . .
C35 C 0.48315(14) 0.11651(13) 0.90328(8) 0.0315(2) Uani 1 1 d . . . . .
H35 H 0.550908 0.208661 0.927720 0.038 Uiso 1 1 calc R . . . .
C36 C 0.53417(15) 0.00156(14) 0.89489(8) 0.0347(3) Uani 1 1 d . . . . .
C37 C 0.43734(16) -0.13596(13) 0.85889(8) 0.0347(3) Uani 1 1 d . . . . .
C38 C 0.28479(16) -0.16395(13) 0.82950(8) 0.0338(3) Uani 1 1 d . . . . .
H38 H 0.220575 -0.257456 0.804794 0.041 Uiso 1 1 calc R . . . .
C39 C 0.67460(19) -0.14614(16) 0.90216(11) 0.0474(4) Uani 1 1 d . . . . .
H39A H 0.703806 -0.168247 0.953843 0.057 Uiso 1 1 calc R . . . .
H39B H 0.746338 -0.167424 0.868915 0.057 Uiso 1 1 calc R . . . .
C40 C 0.42185(14) 0.40286(13) 0.85507(8) 0.0318(3) Uani 1 1 d . . . . .
H40A H 0.468109 0.337569 0.825114 0.048 Uiso 1 1 calc GR . . . .
H40B H 0.499444 0.493450 0.882410 0.048 Uiso 1 1 calc GR . . . .
H40C H 0.338976 0.415877 0.817128 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4290(14) . ?
O1 C2 1.3714(14) . ?
O2 C1 1.4372(17) . ?
O2 C3 1.3758(15) . ?
O3 C16 1.3756(14) . ?
O3 C19 1.4278(16) . ?
O4 C17 1.3763(14) . ?
O4 C19 1.4310(19) . ?
N1 C8 1.4668(14) . ?
N1 C9 1.4333(14) . ?
N1 C20 1.4634(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3858(16) . ?
C2 C7 1.3694(15) . ?
C3 C4 1.3722(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3995(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3980(15) . ?
C6 C7 1.4139(16) . ?
C6 C10 1.4768(15) . ?
C7 C8 1.5068(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3922(14) . ?
C9 C14 1.4240(14) . ?
C10 C11 1.4161(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3642(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.4168(16) . ?
C13 C14 1.4280(15) . ?
C13 C18 1.4257(15) . ?
C14 C15 1.4302(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3568(15) . ?
C16 C17 1.4062(17) . ?
C17 C18 1.3528(18) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 C21 1.4270(14) . ?
O5 C22 1.3730(15) . ?
O6 C21 1.4419(18) . ?
O6 C23 1.3758(15) . ?
O7 C36 1.3741(16) . ?
O7 C39 1.4193(17) . ?
O8 C37 1.3716(15) . ?
O8 C39 1.428(2) . ?
N2 C28 1.4660(15) . ?
N2 C29 1.4288(14) . ?
N2 C40 1.4724(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3846(17) . ?
C22 C27 1.3684(16) . ?
C23 C24 1.3718(19) . ?
C24 H24 0.9500 . ?
C24 C25 1.3986(18) . ?
C25 H25 0.9500 . ?
C25 C26 1.3943(16) . ?
C26 C27 1.4175(16) . ?
C26 C30 1.4781(15) . ?
C27 C28 1.5045(15) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.3931(15) . ?
C29 C34 1.4291(15) . ?
C30 C31 1.4142(16) . ?
C31 H31 0.9500 . ?
C31 C32 1.3699(17) . ?
C32 H32 0.9500 . ?
C32 C33 1.4189(17) . ?
C33 C34 1.4231(16) . ?
C33 C38 1.4284(17) . ?
C34 C35 1.4293(17) . ?
C35 H35 0.9500 . ?
C35 C36 1.3587(16) . ?
C36 C37 1.4036(19) . ?
C37 C38 1.3555(19) . ?
C38 H38 0.9500 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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 O1 C1 105.46(9) . . ?
C3 O2 C1 105.51(9) . . ?
C16 O3 C19 105.27(10) . . ?
C17 O4 C19 105.04(10) . . ?
C9 N1 C8 111.19(9) . . ?
C9 N1 C20 111.48(9) . . ?
C20 N1 C8 112.48(10) . . ?
O1 C1 O2 108.20(10) . . ?
O1 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
O1 C2 C3 110.36(10) . . ?
C7 C2 O1 127.20(10) . . ?
C7 C2 C3 122.45(11) . . ?
O2 C3 C2 109.48(11) . . ?
C4 C3 O2 128.84(11) . . ?
C4 C3 C2 121.67(11) . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.17(10) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.46(11) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 120.25(10) . . ?
C5 C6 C10 123.06(10) . . ?
C7 C6 C10 116.64(9) . . ?
C2 C7 C6 116.98(10) . . ?
C2 C7 C8 124.39(10) . . ?
C6 C7 C8 118.58(10) . . ?
N1 C8 C7 112.28(9) . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 N1 120.76(9) . . ?
C10 C9 C14 121.21(10) . . ?
C14 C9 N1 118.03(9) . . ?
C9 C10 C6 119.42(10) . . ?
C9 C10 C11 118.90(10) . . ?
C11 C10 C6 121.68(9) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.06(10) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.30(10) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 118.79(10) . . ?
C12 C13 C18 120.69(10) . . ?
C18 C13 C14 120.47(10) . . ?
C9 C14 C13 118.65(10) . . ?
C9 C14 C15 121.23(10) . . ?
C13 C14 C15 120.10(10) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 C14 116.86(10) . . ?
C16 C15 H15 121.6 . . ?
O3 C16 C17 108.99(10) . . ?
C15 C16 O3 128.07(11) . . ?
C15 C16 C17 122.90(11) . . ?
O4 C17 C16 109.08(11) . . ?
C18 C17 O4 128.47(11) . . ?
C18 C17 C16 122.42(11) . . ?
C13 C18 H18 121.4 . . ?
C17 C18 C13 117.19(11) . . ?
C17 C18 H18 121.4 . . ?
O3 C19 O4 107.38(10) . . ?
O3 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
O4 C19 H19A 110.2 . . ?
O4 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 O5 C21 105.40(10) . . ?
C23 O6 C21 105.53(9) . . ?
C36 O7 C39 106.23(11) . . ?
C37 O8 C39 106.12(10) . . ?
C28 N2 C40 111.85(9) . . ?
C29 N2 C28 111.36(9) . . ?
C29 N2 C40 112.41(9) . . ?
O5 C21 O6 108.09(10) . . ?
O5 C21 H21A 110.1 . . ?
O5 C21 H21B 110.1 . . ?
O6 C21 H21A 110.1 . . ?
O6 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
O5 C22 C23 110.57(10) . . ?
C27 C22 O5 127.15(11) . . ?
C27 C22 C23 122.28(12) . . ?
O6 C23 C22 109.32(12) . . ?
C24 C23 O6 128.76(11) . . ?
C24 C23 C22 121.91(11) . . ?
C23 C24 H24 121.5 . . ?
C23 C24 C25 116.91(11) . . ?
C25 C24 H24 121.5 . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.81(12) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C27 120.00(11) . . ?
C25 C26 C30 123.65(11) . . ?
C27 C26 C30 116.35(10) . . ?
C22 C27 C26 117.08(10) . . ?
C22 C27 C28 124.27(11) . . ?
C26 C27 C28 118.61(10) . . ?
N2 C28 C27 112.27(9) . . ?
N2 C28 H28A 109.2 . . ?
N2 C28 H28B 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
N2 C29 C34 117.48(10) . . ?
C30 C29 N2 121.44(10) . . ?
C30 C29 C34 121.08(10) . . ?
C29 C30 C26 119.44(10) . . ?
C29 C30 C31 118.83(10) . . ?
C31 C30 C26 121.71(10) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.28(11) . . ?
C32 C31 H31 119.4 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 121.05(11) . . ?
C33 C32 H32 119.5 . . ?
C32 C33 C34 118.84(11) . . ?
C32 C33 C38 120.60(11) . . ?
C34 C33 C38 120.54(11) . . ?
C29 C34 C35 121.00(10) . . ?
C33 C34 C29 118.89(10) . . ?
C33 C34 C35 120.10(10) . . ?
C34 C35 H35 121.5 . . ?
C36 C35 C34 116.92(12) . . ?
C36 C35 H35 121.5 . . ?
O7 C36 C37 109.31(11) . . ?
C35 C36 O7 127.67(13) . . ?
C35 C36 C37 123.02(12) . . ?
O8 C37 C36 109.30(12) . . ?
C38 C37 O8 128.54(12) . . ?
C38 C37 C36 122.17(11) . . ?
C33 C38 H38 121.4 . . ?
C37 C38 C33 117.25(12) . . ?
C37 C38 H38 121.4 . . ?
O7 C39 O8 108.54(11) . . ?
O7 C39 H39A 110.0 . . ?
O7 C39 H39B 110.0 . . ?
O8 C39 H39A 110.0 . . ?
O8 C39 H39B 110.0 . . ?
H39A C39 H39B 108.4 . . ?
N2 C40 H40A 109.5 . . ?
N2 C40 H40B 109.5 . . ?
N2 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
