# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2055692'
loop_
_audit_author_name
_audit_author_address
'Lifu Cao'
;JILIN University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C2.364 H1.636 N0.364 O0.545'
_chemical_formula_sum            'C2.36 H1.64 N0.36 O0.55'
_chemical_formula_weight         43.86
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.331(3)
_cell_length_b                   7.1760(7)
_cell_length_c                   13.4905(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.392(6)
_cell_angle_gamma                90.00
_cell_volume                     2220.9(4)
_cell_formula_units_Z            44
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    151.0
_cell_measurement_theta_max      26.765
_cell_measurement_theta_min      2.974
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23886
_diffrn_reflns_theta_full        26.72
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      151.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2137
_reflns_number_total             2350
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.40A (bu, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (bu, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XS n/a (Sheldrick, 2008)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0391P)²+2.0912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0862
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10101(4) 0.54374(11) 0.14092(7) 0.0239(2) Uani 1 1 d . . .
O2 O -0.19674(3) -0.07525(11) 0.11245(7) 0.0219(2) Uani 1 1 d . . .
O3 O 0.16277(4) 0.31751(15) 0.18621(9) 0.0374(3) Uani 1 1 d . . .
N4 N 0.11388(4) 0.37765(14) 0.15799(8) 0.0211(2) Uani 1 1 d . . .
C5 C -0.02953(5) 0.18630(15) 0.10388(9) 0.0157(2) Uani 1 1 d . . .
C6 C -0.09231(4) 0.45246(16) 0.09044(9) 0.0181(2) Uani 1 1 d . . .
C7 C -0.01570(5) -0.00404(16) 0.12107(9) 0.0180(2) Uani 1 1 d . . .
H7 H -0.0447 -0.0911 0.1129 0.022 Uiso 1 1 calc R . .
N8 N -0.09284(4) 0.60998(14) 0.10488(9) 0.0258(2) Uani 1 1 d . . .
C9 C -0.22507(5) 0.08341(15) 0.05677(9) 0.0184(2) Uani 1 1 d . . .
C10 C -0.13494(5) 0.14282(16) 0.04815(9) 0.0184(2) Uani 1 1 d . . .
H10 H -0.1291 0.0130 0.0443 0.022 Uiso 1 1 calc R . .
C11 C 0.08266(5) 0.05674(16) 0.16081(9) 0.0200(2) Uani 1 1 d . . .
H11 H 0.1205 0.0143 0.1796 0.024 Uiso 1 1 calc R . .
C12 C 0.01361(4) 0.31197(15) 0.11593(8) 0.0160(2) Uani 1 1 d . . .
H12 H 0.0057 0.4418 0.1054 0.019 Uiso 1 1 calc R . .
C13 C -0.21957(5) 0.36611(16) -0.03566(9) 0.0191(2) Uani 1 1 d . . .
H13 H -0.1991 0.4446 -0.0608 0.023 Uiso 1 1 calc R . .
C14 C -0.08831(5) 0.25401(15) 0.07684(9) 0.0160(2) Uani 1 1 d . . .
C15 C 0.06841(5) 0.24379(16) 0.14357(9) 0.0176(2) Uani 1 1 d . . .
C16 C -0.19357(5) 0.20087(16) 0.02230(9) 0.0183(2) Uani 1 1 d . . .
C17 C 0.03962(5) -0.06686(16) 0.14973(9) 0.0205(2) Uani 1 1 d . . .
H17 H 0.0482 -0.1962 0.1619 0.025 Uiso 1 1 calc R . .
C18 C -0.22605(5) -0.19687(17) 0.15223(11) 0.0263(3) Uani 1 1 d . . .
H18A H -0.2635 -0.2351 0.0880 0.039 Uiso 1 1 calc R . .
H18B H -0.2328 -0.1314 0.2085 0.039 Uiso 1 1 calc R . .
H18C H -0.2019 -0.3073 0.1874 0.039 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 N4 1.2295(13) . ?
O2 C9 1.3663(14) . ?
O2 C18 1.4325(14) . ?
O3 N4 1.2277(13) . ?
N4 C15 1.4713(14) . ?
C5 C7 1.4033(15) . ?
C5 C12 1.3959(15) . ?
C5 C14 1.4868(14) . ?
C6 N8 1.1483(15) . ?
C6 C14 1.4463(15) . ?
C7 H7 0.9500 . ?
C7 C17 1.3862(16) . ?
C9 C13 1.3893(15) 7_455 ?
C9 C16 1.4116(15) . ?
C10 H10 0.9500 . ?
C10 C14 1.3517(15) . ?
C10 C16 1.4664(15) . ?
C11 H11 0.9500 . ?
C11 C15 1.3823(16) . ?
C11 C17 1.3881(16) . ?
C12 H12 0.9500 . ?
C12 C15 1.3902(15) . ?
C13 C9 1.3893(16) 7_455 ?
C13 H13 0.9500 . ?
C13 C16 1.4002(16) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C9 O2 C18 117.69(9) . . ?
O1 N4 C15 118.47(9) . . ?
O3 N4 O1 123.32(10) . . ?
O3 N4 C15 118.21(10) . . ?
C7 C5 C14 120.87(10) . . ?
C12 C5 C7 118.63(10) . . ?
C12 C5 C14 120.47(10) . . ?
N8 C6 C14 176.88(12) . . ?
C5 C7 H7 119.5 . . ?
C17 C7 C5 120.97(10) . . ?
C17 C7 H7 119.5 . . ?
O2 C9 C13 124.38(10) . 7_455 ?
O2 C9 C16 115.36(10) . . ?
C13 C9 C16 120.25(10) 7_455 . ?
C14 C10 H10 116.5 . . ?
C14 C10 C16 127.06(10) . . ?
C16 C10 H10 116.5 . . ?
C15 C11 H11 121.2 . . ?
C15 C11 C17 117.56(10) . . ?
C17 C11 H11 121.2 . . ?
C5 C12 H12 120.6 . . ?
C15 C12 C5 118.82(10) . . ?
C15 C12 H12 120.6 . . ?
C9 C13 H13 119.6 7_455 . ?
C9 C13 C16 120.76(10) 7_455 . ?
C16 C13 H13 119.6 . . ?
C6 C14 C5 114.99(9) . . ?
C10 C14 C5 124.55(10) . . ?
C10 C14 C6 120.34(10) . . ?
C11 C15 N4 118.41(10) . . ?
C11 C15 C12 123.16(10) . . ?
C12 C15 N4 118.41(10) . . ?
C9 C16 C10 118.18(10) . . ?
C13 C16 C9 118.97(10) . . ?
C13 C16 C10 122.85(10) . . ?
C7 C17 C11 120.85(11) . . ?
C7 C17 H17 119.6 . . ?
C11 C17 H17 119.6 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C15 C11 178.87(10) . . . . ?
O1 N4 C15 C12 -2.65(15) . . . . ?
O2 C9 C16 C10 0.35(15) . . . . ?
O2 C9 C16 C13 179.79(9) . . . . ?
O3 N4 C15 C11 -0.93(15) . . . . ?
O3 N4 C15 C12 177.55(10) . . . . ?
C5 C7 C17 C11 -0.81(16) . . . . ?
C5 C12 C15 N4 -178.97(9) . . . . ?
C5 C12 C15 C11 -0.57(16) . . . . ?
C7 C5 C12 C15 0.51(15) . . . . ?
C7 C5 C14 C6 164.55(10) . . . . ?
C7 C5 C14 C10 -11.52(16) . . . . ?
N8 C6 C14 C5 -27(2) . . . . ?
N8 C6 C14 C10 149(2) . . . . ?
C9 C13 C16 C9 1.52(18) 7_455 . . . ?
C9 C13 C16 C10 -179.06(10) 7_455 . . . ?
C12 C5 C7 C17 0.17(15) . . . . ?
C12 C5 C14 C6 -13.58(14) . . . . ?
C12 C5 C14 C10 170.35(10) . . . . ?
C13 C9 C16 C10 179.04(10) 7_455 . . . ?
C13 C9 C16 C13 -1.51(18) 7_455 . . . ?
C14 C5 C7 C17 -178.00(10) . . . . ?
C14 C5 C12 C15 178.67(9) . . . . ?
C14 C10 C16 C9 -144.31(11) . . . . ?
C14 C10 C16 C13 36.27(17) . . . . ?
C15 C11 C17 C7 0.74(16) . . . . ?
C16 C10 C14 C5 179.02(10) . . . . ?
C16 C10 C14 C6 3.15(17) . . . . ?
C17 C11 C15 N4 178.35(9) . . . . ?
C17 C11 C15 C12 -0.05(16) . . . . ?
C18 O2 C9 C13 -0.39(16) . . . 7_455 ?
C18 O2 C9 C16 178.25(10) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2055693'
loop_
_audit_author_name
_audit_author_address
'Lifu Cao'
;JILIN University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_audit_creation_date             2021-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H18 N4 O6'
_chemical_formula_sum            'C26 H18 N4 O6'
_chemical_formula_weight         482.44
_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                   4.5740(5)
_cell_length_b                   10.4956(12)
_cell_length_c                   22.772(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.330(4)
_cell_angle_gamma                90
_cell_volume                     1091.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.554
_cell_measurement_theta_min      2.641
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            56919
_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         31.622
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      100.0
_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                2883
_reflns_number_total             3650
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.1045
_refine_ls_restrained_S_all      1.230
_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)+(0.0354P)²+3.9843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.1650(6) 0.4482(3) 0.25794(12) 0.0324(6) Uani 1 1 d . . . . .
O2 O -0.4617(6) 0.3014(3) 0.22441(12) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.8212(5) 0.5795(2) 0.38803(10) 0.0191(5) Uani 1 1 d . . . . .
N0AA N 0.4216(7) 0.1355(3) 0.53393(14) 0.0280(7) Uani 1 1 d . . . . .
N1 N -0.2681(6) 0.3404(3) 0.25937(12) 0.0202(5) Uani 1 1 d . . . . .
C2 C -0.1559(6) 0.2524(3) 0.30613(13) 0.0158(5) Uani 1 1 d . . . . .
C3 C 0.0591(6) 0.2980(3) 0.34602(13) 0.0157(5) Uani 1 1 d . . . . .
H3 H 0.1373 0.3811 0.3417 0.019 Uiso 1 1 calc R . . . .
C4 C 0.1594(6) 0.2201(3) 0.39278(12) 0.0132(5) Uani 1 1 d . . . . .
C5 C 0.3841(6) 0.2666(3) 0.43747(12) 0.0141(5) Uani 1 1 d . . . . .
C6 C 0.5486(6) 0.3722(3) 0.42918(13) 0.0137(5) Uani 1 1 d . . . . .
H6 H 0.5088 0.4129 0.3923 0.016 Uiso 1 1 calc R . . . .
C7 C 0.7747(6) 0.4344(3) 0.46665(12) 0.0130(5) Uani 1 1 d . . . . .
C8 C 1.1347(6) 0.6059(3) 0.47657(13) 0.0153(5) Uani 1 1 d . . . . .
H8 H 1.2256 0.6780 0.4602 0.018 Uiso 1 1 calc R . . . .
C9 C 0.9143(6) 0.5425(3) 0.44364(13) 0.0141(5) Uani 1 1 d . . . . .
C10 C 0.0348(6) 0.0988(3) 0.39737(14) 0.0176(6) Uani 1 1 d . . . . .
H10 H 0.0984 0.0449 0.4291 0.021 Uiso 1 1 calc R . . . .
C11 C -0.1803(7) 0.0557(3) 0.35645(14) 0.0201(6) Uani 1 1 d . . . . .
H11 H -0.2600 -0.0273 0.3604 0.024 Uiso 1 1 calc R . . . .
C12 C -0.2796(7) 0.1330(3) 0.30983(14) 0.0196(6) Uani 1 1 d . . . . .
H12 H -0.4268 0.1047 0.2817 0.024 Uiso 1 1 calc R . . . .
C13 C 0.4097(6) 0.1941(3) 0.49126(14) 0.0179(6) Uani 1 1 d . . . . .
C14 C 0.9898(7) 0.6747(3) 0.36028(14) 0.0223(6) Uani 1 1 d . . . . .
H14A H 0.9775 0.7553 0.3818 0.033 Uiso 1 1 calc GR . . . .
H14B H 0.9128 0.6867 0.3196 0.033 Uiso 1 1 calc GR . . . .
H14C H 1.1948 0.6474 0.3605 0.033 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 N1 1.227(4) . ?
O2 N1 1.226(4) . ?
O3 C9 1.369(3) . ?
O3 C14 1.432(4) . ?
N0AA C13 1.149(4) . ?
N1 C2 1.479(4) . ?
C2 C3 1.385(4) . ?
C2 C12 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(4) . ?
C4 C5 1.486(4) . ?
C4 C10 1.401(4) . ?
C5 C6 1.359(4) . ?
C5 C13 1.441(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.456(4) . ?
C7 C8 1.400(4) 3_766 ?
C7 C9 1.417(4) . ?
C8 C7 1.400(4) 3_766 ?
C8 H8 0.9500 . ?
C8 C9 1.390(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(5) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C9 O3 C14 117.4(2) . . ?
O1 N1 C2 118.5(3) . . ?
O2 N1 O1 123.7(3) . . ?
O2 N1 C2 117.8(3) . . ?
C3 C2 N1 117.4(3) . . ?
C12 C2 N1 119.0(3) . . ?
C12 C2 C3 123.5(3) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 C10 118.1(3) . . ?
C10 C4 C5 121.0(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 C13 122.0(3) . . ?
C13 C5 C4 115.3(3) . . ?
C5 C6 H6 114.2 . . ?
C5 C6 C7 131.6(3) . . ?
C7 C6 H6 114.2 . . ?
C8 C7 C6 124.6(3) 3_766 . ?
C8 C7 C9 117.9(2) 3_766 . ?
C9 C7 C6 117.5(3) . . ?
C7 C8 H8 119.3 3_766 . ?
C9 C8 C7 121.3(3) . 3_766 ?
C9 C8 H8 119.3 . . ?
O3 C9 C7 116.5(2) . . ?
O3 C9 C8 122.7(3) . . ?
C8 C9 C7 120.8(3) . . ?
C4 C10 H10 119.3 . . ?
C11 C10 C4 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C2 C12 C11 117.4(3) . . ?
C2 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
N0AA C13 C5 178.0(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C3 0.5(4) . . . . ?
O1 N1 C2 C12 177.0(3) . . . . ?
O2 N1 C2 C3 -178.9(3) . . . . ?
O2 N1 C2 C12 -2.4(4) . . . . ?
N1 C2 C3 C4 176.5(3) . . . . ?
N1 C2 C12 C11 -176.3(3) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
C2 C3 C4 C10 -0.5(4) . . . . ?
C3 C2 C12 C11 0.0(5) . . . . ?
C3 C4 C5 C6 -14.8(4) . . . . ?
C3 C4 C5 C13 163.3(3) . . . . ?
C3 C4 C10 C11 0.8(4) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C4 C10 C11 C12 -0.6(5) . . . . ?
C5 C4 C10 C11 178.6(3) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . 3_766 ?
C5 C6 C7 C9 177.6(3) . . . . ?
C6 C7 C9 O3 0.6(4) . . . . ?
C6 C7 C9 C8 -179.2(3) . . . . ?
C7 C8 C9 O3 -179.9(3) 3_766 . . . ?
C7 C8 C9 C7 -0.2(5) 3_766 . . . ?
C8 C7 C9 O3 179.9(3) 3_766 . . . ?
C8 C7 C9 C8 0.2(5) 3_766 . . . ?
C10 C4 C5 C6 167.5(3) . . . . ?
C10 C4 C5 C13 -14.4(4) . . . . ?
C10 C11 C12 C2 0.2(5) . . . . ?
C12 C2 C3 C4 0.2(4) . . . . ?
C13 C5 C6 C7 1.3(5) . . . . ?
C14 O3 C9 C7 -170.0(3) . . . . ?
C14 O3 C9 C8 9.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
