# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
#
# This file replaces the original version made available on 3rd April 2025, 
# which contained incorrect CCDC data files
#
# 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_mo_dv_b1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2mbg5m
_database_code_depnum_ccdc_archive 'CCDC 2423120'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D5TC00619H 2025
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2025-02-11 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_audit_creation_date             2025-01-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 F N2 O3'
_chemical_formula_sum            'C12 H9 F N2 O3'
_chemical_formula_weight         248.21
_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'
F F 0.0171 0.0103 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3988(8)
_cell_length_b                   11.3929(12)
_cell_length_c                   13.6438(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.437(4)
_cell_angle_gamma                90
_cell_volume                     1127.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1053
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.27
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0814 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.029
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15629
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1081
_reflns_number_total             2307
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0794
_refine_ls_restrained_S_all      1.044
_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)+(0.1230P)²+0.7490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2271
_refine_ls_wR_factor_ref         0.2817
_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:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
C1 C 0.1944(6) 0.3752(4) 0.3932(3) 0.0652(12) Uani 1 1 d . . . . .
C2 C 0.1625(6) 0.2579(4) 0.3968(3) 0.0597(11) Uani 1 1 d . . . . .
C3 C -0.0148(6) 0.2446(4) 0.4196(3) 0.0645(12) Uani 1 1 d . . . . .
N4 N -0.0879(5) 0.3458(4) 0.4283(3) 0.0772(12) Uani 1 1 d . . . . .
O5 O 0.0440(5) 0.4301(3) 0.4114(3) 0.0811(10) Uani 1 1 d . . . . .
C6 C -0.1202(6) 0.1368(4) 0.4353(4) 0.0797(15) Uani 1 1 d . . . . .
H6A H -0.062041 0.099370 0.496488 0.120 Uiso 1 1 calc R U . . .
H6B H -0.121985 0.083772 0.380419 0.120 Uiso 1 1 calc R U . . .
H6C H -0.244223 0.157923 0.439017 0.120 Uiso 1 1 calc R U . . .
N7 N 0.2845(5) 0.1672(4) 0.3800(3) 0.0729(11) Uani 1 1 d . . . . .
C8 C 0.3406(7) 0.4463(4) 0.3747(4) 0.0811(15) Uani 1 1 d . . . . .
H8 H 0.440437 0.410684 0.354728 0.097 Uiso 1 1 calc R U . . .
C9 C 0.3403(7) 0.5636(4) 0.3851(4) 0.0781(14) Uani 1 1 d . . . . .
H9 H 0.237892 0.596618 0.404428 0.094 Uiso 1 1 calc R U . . .
C10 C 0.4860(6) 0.6452(4) 0.3688(3) 0.0663(12) Uani 1 1 d . . . . .
C11 C 0.4529(7) 0.7652(4) 0.3690(3) 0.0708(13) Uani 1 1 d . . . . .
H11 H 0.341879 0.792159 0.382632 0.085 Uiso 1 1 calc R U . . .
C12 C 0.5804(8) 0.8451(4) 0.3495(4) 0.0792(14) Uani 1 1 d . . . . .
H12 H 0.557324 0.925340 0.349715 0.095 Uiso 1 1 calc R U . . .
C13 C 0.7430(7) 0.8025(4) 0.3296(4) 0.0731(13) Uani 1 1 d . . . . .
C14 C 0.7822(7) 0.6861(4) 0.3291(4) 0.0716(13) Uani 1 1 d . . . . .
H14 H 0.893631 0.660148 0.315228 0.086 Uiso 1 1 calc R U . . .
C15 C 0.6540(6) 0.6075(4) 0.3496(3) 0.0675(12) Uani 1 1 d . . . . .
H15 H 0.680163 0.527602 0.350663 0.081 Uiso 1 1 calc R U . . .
F16 F 0.8702(5) 0.8792(3) 0.3096(3) 0.1116(12) Uani 1 1 d . . . . .
O17 O 0.2425(5) 0.0663(3) 0.3955(3) 0.1009(13) Uani 1 1 d . . . . .
O18 O 0.4231(5) 0.1933(3) 0.3496(3) 0.1014(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.360(6) . ?
C1 O5 1.342(5) . ?
C1 C8 1.413(6) . ?
C2 C3 1.416(6) . ?
C2 N7 1.420(5) . ?
C3 N4 1.289(6) . ?
C3 C6 1.492(6) . ?
N4 O5 1.421(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N7 O17 1.220(5) . ?
N7 O18 1.217(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.344(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.472(6) . ?
C10 C11 1.390(6) . ?
C10 C15 1.388(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(7) . ?
C13 C14 1.358(7) . ?
C13 F16 1.351(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(6) . ?
C15 H15 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
C2 C1 C8 135.6(4) . . ?
O5 C1 C2 107.2(4) . . ?
O5 C1 C8 117.2(4) . . ?
C1 C2 C3 106.8(4) . . ?
C1 C2 N7 126.1(4) . . ?
C3 C2 N7 127.1(4) . . ?
C2 C3 C6 130.8(4) . . ?
N4 C3 C2 110.4(4) . . ?
N4 C3 C6 118.9(4) . . ?
C3 N4 O5 106.0(3) . . ?
C1 O5 N4 109.7(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O17 N7 C2 117.8(4) . . ?
O18 N7 C2 118.9(4) . . ?
O18 N7 O17 123.4(4) . . ?
C1 C8 H8 118.8 . . ?
C9 C8 C1 122.3(5) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 116.7 . . ?
C8 C9 C10 126.5(5) . . ?
C10 C9 H9 116.7 . . ?
C11 C10 C9 119.1(4) . . ?
C15 C10 C9 122.9(4) . . ?
C15 C10 C11 118.0(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(5) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.8(5) . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 122.8(5) . . ?
F16 C13 C12 119.0(4) . . ?
F16 C13 C14 118.2(5) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(4) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(4) . . ?
C14 C15 H15 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6B F16 0.96 2.52 3.393(6) 151.3 1_445 yes
C6 H6C O18 0.96 2.55 3.411(6) 148.8 1_455 yes
C15 H15 O5 0.93 2.88 3.487(6) 124.2 1_655 yes
C15 H15 F16 0.93 2.73 3.370(6) 126.8 2_645 yes

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
C1 C2 C3 N4 0.8(5) . . . . ?
C1 C2 C3 C6 -178.4(5) . . . . ?
C1 C2 N7 O17 173.1(5) . . . . ?
C1 C2 N7 O18 -8.1(7) . . . . ?
C1 C8 C9 C10 179.3(5) . . . . ?
C2 C1 O5 N4 0.6(5) . . . . ?
C2 C1 C8 C9 -173.8(5) . . . . ?
C2 C3 N4 O5 -0.4(5) . . . . ?
C3 C2 N7 O17 -7.4(7) . . . . ?
C3 C2 N7 O18 171.5(4) . . . . ?
C3 N4 O5 C1 -0.2(5) . . . . ?
O5 C1 C2 C3 -0.8(5) . . . . ?
O5 C1 C2 N7 178.8(4) . . . . ?
O5 C1 C8 C9 7.0(8) . . . . ?
C6 C3 N4 O5 178.9(4) . . . . ?
N7 C2 C3 N4 -178.9(4) . . . . ?
N7 C2 C3 C6 2.0(8) . . . . ?
C8 C1 C2 C3 179.9(5) . . . . ?
C8 C1 C2 N7 -0.5(9) . . . . ?
C8 C1 O5 N4 -179.9(4) . . . . ?
C8 C9 C10 C11 171.0(5) . . . . ?
C8 C9 C10 C15 -6.6(8) . . . . ?
C9 C10 C11 C12 -176.8(5) . . . . ?
C9 C10 C15 C14 176.2(4) . . . . ?
C10 C11 C12 C13 0.0(7) . . . . ?
C11 C10 C15 C14 -1.5(7) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C11 C12 C13 F16 179.6(4) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C10 1.1(7) . . . . ?
C15 C10 C11 C12 0.9(7) . . . . ?
F16 C13 C14 C15 179.8(4) . . . . ?

_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_mo_dv_b4_4_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2mbg6n
_database_code_depnum_ccdc_archive 'CCDC 2423121'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D5TC00619H 2025
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2025-02-11 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
_audit_creation_date             2025-01-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 I N2 O3'
_chemical_formula_sum            'C12 H9 I N2 O3'
_chemical_formula_weight         356.11
_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'
I I -0.4742 1.8119 '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                   8.1177(16)
_cell_length_b                   8.4258(18)
_cell_length_c                   10.345(2)
_cell_angle_alpha                89.257(10)
_cell_angle_beta                 73.519(9)
_cell_angle_gamma                68.680(9)
_cell_volume                     628.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4904
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    2.548
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.7681.
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    1.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.056
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_unetI/netI     0.1267
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13461
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.063
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.963
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1561
_reflns_number_total             2775
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.275
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.020
_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)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1147
_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:
 C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
C1 C 0.8149(7) 0.6258(7) 0.3724(5) 0.0418(12) Uani 1 1 d . . . . .
C2 C 0.9377(6) 0.5198(6) 0.2584(5) 0.0394(12) Uani 1 1 d . . . . .
C3 C 1.1178(7) 0.5107(7) 0.2546(5) 0.0444(13) Uani 1 1 d . . . . .
N4 N 1.1088(6) 0.6001(6) 0.3572(4) 0.0494(12) Uani 1 1 d . . . . .
O5 O 0.9179(4) 0.6753(5) 0.4337(3) 0.0467(9) Uani 1 1 d . . . . .
C6 C 1.3002(6) 0.4156(7) 0.1522(5) 0.0572(16) Uani 1 1 d . . . . .
H6A H 1.298134 0.455362 0.065128 0.086 Uiso 1 1 calc R U . . .
H6B H 1.323179 0.295359 0.147683 0.086 Uiso 1 1 calc R U . . .
H6C H 1.396560 0.434743 0.178084 0.086 Uiso 1 1 calc R U . . .
N7 N 0.8873(6) 0.4411(6) 0.1630(4) 0.0491(11) Uani 1 1 d . . . . .
C8 C 0.6215(6) 0.6845(6) 0.4372(5) 0.0426(12) Uani 1 1 d . . . . .
H8 H 0.550610 0.646909 0.397823 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5340(7) 0.7909(7) 0.5518(5) 0.0459(13) Uani 1 1 d . . . . .
H9 H 0.608276 0.824874 0.589957 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3390(6) 0.8584(6) 0.6222(5) 0.0394(12) Uani 1 1 d . . . . .
C11 C 0.2707(6) 0.9659(7) 0.7438(5) 0.0473(14) Uani 1 1 d . . . . .
H11 H 0.353767 0.989637 0.778819 0.057 Uiso 1 1 calc R U . . .
C12 C 0.0841(7) 1.0369(7) 0.8125(5) 0.0449(13) Uani 1 1 d . . . . .
H12 H 0.042084 1.108718 0.892112 0.054 Uiso 1 1 calc R U . . .
C13 C -0.0401(6) 1.0006(7) 0.7621(5) 0.0416(12) Uani 1 1 d . . . . .
C14 C 0.0203(6) 0.8948(7) 0.6435(5) 0.0477(14) Uani 1 1 d . . . . .
H14 H -0.064308 0.871509 0.610013 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2076(6) 0.8240(7) 0.5750(5) 0.0466(14) Uani 1 1 d . . . . .
H15 H 0.247951 0.751752 0.495760 0.056 Uiso 1 1 calc R U . . .
I16 I -0.32375(5) 1.10808(5) 0.86431(4) 0.0647(2) Uani 1 1 d . . . . .
O17 O 1.0134(6) 0.3428(5) 0.0698(4) 0.0641(11) Uani 1 1 d . . . . .
O18 O 0.7225(6) 0.4720(6) 0.1785(4) 0.0726(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(6) . ?
C1 O5 1.355(5) . ?
C1 C8 1.416(6) . ?
C2 C3 1.424(6) . ?
C2 N7 1.423(6) . ?
C3 N4 1.279(6) . ?
C3 C6 1.492(6) . ?
N4 O5 1.426(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N7 O17 1.228(6) . ?
N7 O18 1.228(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.342(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.436(6) . ?
C10 C11 1.407(6) . ?
C10 C15 1.408(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(6) . ?
C13 C14 1.382(7) . ?
C13 I16 2.089(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(7) . ?
C15 H15 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
C2 C1 C8 136.3(4) . . ?
O5 C1 C2 106.2(4) . . ?
O5 C1 C8 117.5(4) . . ?
C1 C2 C3 107.0(4) . . ?
C1 C2 N7 124.8(4) . . ?
N7 C2 C3 128.2(4) . . ?
C2 C3 C6 129.3(5) . . ?
N4 C3 C2 110.4(4) . . ?
N4 C3 C6 120.3(4) . . ?
C3 N4 O5 106.6(4) . . ?
C1 O5 N4 109.8(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O17 N7 C2 117.3(5) . . ?
O18 N7 C2 119.2(4) . . ?
O18 N7 O17 123.5(5) . . ?
C1 C8 H8 118.0 . . ?
C9 C8 C1 124.1(4) . . ?
C9 C8 H8 118.0 . . ?
C8 C9 H9 116.3 . . ?
C8 C9 C10 127.5(4) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 C15 116.8(4) . . ?
C15 C10 C9 123.2(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.8(5) . . ?
C12 C13 I16 120.1(4) . . ?
C14 C13 I16 119.1(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.6(4) . . ?
C14 C15 H15 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14 O5 0.93 2.55 3.327(6) 141.8 1_455 yes
C15 H15 N4 0.93 2.64 3.393(6) 138.3 1_455 yes

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
C1 C2 C3 N4 0.9(7) . . . . ?
C1 C2 C3 C6 -179.2(5) . . . . ?
C1 C2 N7 O17 -176.4(5) . . . . ?
C1 C2 N7 O18 2.5(9) . . . . ?
C1 C8 C9 C10 178.8(5) . . . . ?
C2 C1 O5 N4 0.2(6) . . . . ?
C2 C1 C8 C9 179.8(6) . . . . ?
C2 C3 N4 O5 -0.8(6) . . . . ?
C3 C2 N7 O17 5.6(9) . . . . ?
C3 C2 N7 O18 -175.4(5) . . . . ?
C3 N4 O5 C1 0.4(6) . . . . ?
O5 C1 C2 C3 -0.6(6) . . . . ?
O5 C1 C2 N7 -178.9(5) . . . . ?
O5 C1 C8 C9 2.8(9) . . . . ?
C6 C3 N4 O5 179.4(4) . . . . ?
N7 C2 C3 N4 179.1(5) . . . . ?
N7 C2 C3 C6 -1.0(10) . . . . ?
C8 C1 C2 C3 -177.9(6) . . . . ?
C8 C1 C2 N7 3.9(11) . . . . ?
C8 C1 O5 N4 178.0(4) . . . . ?
C8 C9 C10 C11 178.4(6) . . . . ?
C8 C9 C10 C15 -2.3(9) . . . . ?
C9 C10 C11 C12 178.2(5) . . . . ?
C9 C10 C15 C14 -178.2(5) . . . . ?
C10 C11 C12 C13 0.8(9) . . . . ?
C11 C10 C15 C14 1.1(8) . . . . ?
C11 C12 C13 C14 -0.4(9) . . . . ?
C11 C12 C13 I16 -179.7(4) . . . . ?
C12 C13 C14 C15 0.3(9) . . . . ?
C13 C14 C15 C10 -0.8(9) . . . . ?
C15 C10 C11 C12 -1.2(8) . . . . ?
I16 C13 C14 C15 179.7(4) . . . . ?

_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_b7_ep
_audit_block_doi                 10.5517/ccdc.csd.cc2mbg7p
_database_code_depnum_ccdc_archive 'CCDC 2423122'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D5TC00619H 2025
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2025-02-11 deposited with the CCDC.	2025-05-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_b7_ep               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01146 Ang.
RESPONSE: The single crystal is of low quality, and all data were collected at room temperature
;
# Added during the CSD deposition process: Tuesday 11 February 2025 07:16 PM
# end Validation Reply Form

_audit_creation_date             2025-01-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N3 O3'
_chemical_formula_sum            'C14 H15 N3 O3'
_chemical_formula_weight         273.29
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   22.0846(11)
_cell_length_b                   4.0685(3)
_cell_length_c                   29.5491(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2655.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2269
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1167 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.8881.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            31056
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         2.303
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2904
_reflns_number_total             6095
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6095
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      0.989
_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)+(0.1233P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.2350
_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:
 C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C7B(H7B),
 C8B(H8B), C10B(H10B), C11B(H11B), C13B(H13B), C14B(H14B)
2.b Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C), C6B(H6BA,
 H6BB,H6BC), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F)
;
_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
C1A C 0.4204(3) 0.373(2) 0.3716(3) 0.0492(17) Uani 1 1 d . . . . .
C2A C 0.4209(3) 0.4426(19) 0.3262(2) 0.0483(18) Uani 1 1 d . . . . .
C3A C 0.3676(5) 0.293(2) 0.3071(4) 0.052(3) Uani 1 1 d . . . . .
N4A N 0.3396(3) 0.130(2) 0.3384(3) 0.0659(19) Uani 1 1 d . . . . .
O5A O 0.3720(3) 0.1827(18) 0.3789(2) 0.0646(18) Uani 1 1 d . . . . .
C6A C 0.3433(5) 0.298(3) 0.2610(4) 0.069(3) Uani 1 1 d . . . . .
H6AA H 0.311676 0.137189 0.258398 0.104 Uiso 1 1 calc R U . . .
H6AB H 0.374994 0.248287 0.239926 0.104 Uiso 1 1 calc R U . . .
H6AC H 0.327133 0.512233 0.254568 0.104 Uiso 1 1 calc R U . . .
C7A C 0.4593(3) 0.4488(19) 0.4085(2) 0.0489(18) Uani 1 1 d . . . . .
H7A H 0.494193 0.570235 0.403101 0.059 Uiso 1 1 calc R U . . .
C8A C 0.4471(4) 0.350(2) 0.4511(3) 0.055(2) Uani 1 1 d . . . . .
H8A H 0.411469 0.230814 0.454714 0.066 Uiso 1 1 calc R U . . .
C9A C 0.4817(3) 0.4046(19) 0.4917(3) 0.0471(17) Uani 1 1 d . . . . .
C10A C 0.4584(4) 0.2825(19) 0.5334(3) 0.046(2) Uani 1 1 d . . . . .
H10A H 0.420726 0.180050 0.534185 0.056 Uiso 1 1 calc R U . . .
C11A C 0.4921(4) 0.317(2) 0.5731(3) 0.054(2) Uani 1 1 d . . . . .
H11A H 0.477142 0.230810 0.600046 0.064 Uiso 1 1 calc R U . . .
C12A C 0.5482(3) 0.4792(17) 0.5730(2) 0.0440(16) Uani 1 1 d . . . . .
C13A C 0.5694(3) 0.607(2) 0.5319(2) 0.0482(17) Uani 1 1 d . . . . .
H13A H 0.605889 0.720359 0.531105 0.058 Uiso 1 1 calc R U . . .
C14A C 0.5367(3) 0.5658(18) 0.4930(2) 0.0494(18) Uani 1 1 d . . . . .
H14A H 0.552230 0.650358 0.466166 0.059 Uiso 1 1 calc R U . . .
N15A N 0.5807(3) 0.5093(16) 0.6126(2) 0.0587(17) Uani 1 1 d . . . . .
C16A C 0.6398(5) 0.680(3) 0.6114(4) 0.071(3) Uani 1 1 d . . . . .
H16A H 0.666008 0.572269 0.590153 0.106 Uiso 1 1 calc R U . . .
H16B H 0.657838 0.673358 0.640982 0.106 Uiso 1 1 calc R U . . .
H16C H 0.633926 0.904192 0.602445 0.106 Uiso 1 1 calc R U . . .
C17A C 0.5572(5) 0.388(3) 0.6553(3) 0.076(3) Uani 1 1 d . . . . .
H17A H 0.589873 0.365085 0.676516 0.114 Uiso 1 1 calc R U . . .
H17B H 0.538310 0.178474 0.650645 0.114 Uiso 1 1 calc R U . . .
H17C H 0.528010 0.540838 0.666958 0.114 Uiso 1 1 calc R U . . .
N18A N 0.4647(3) 0.644(2) 0.3040(2) 0.0594(17) Uani 1 1 d . . . . .
O19A O 0.4543(4) 0.7135(17) 0.2625(2) 0.074(2) Uani 1 1 d . . . . .
O20A O 0.5086(4) 0.7396(17) 0.3235(3) 0.085(3) Uani 1 1 d . . . . .
C1B C 0.8306(3) 0.862(2) 0.6252(2) 0.0474(17) Uani 1 1 d . . . . .
C2B C 0.8312(3) 0.9439(19) 0.6699(2) 0.0506(19) Uani 1 1 d . . . . .
C3B C 0.8835(5) 0.793(2) 0.6889(4) 0.054(3) Uani 1 1 d . . . . .
N4B N 0.9138(3) 0.647(2) 0.6583(2) 0.0657(19) Uani 1 1 d . . . . .
O5B O 0.8801(3) 0.6870(17) 0.6168(2) 0.0603(17) Uani 1 1 d . . . . .
C6B C 0.9066(5) 0.802(3) 0.7372(4) 0.076(3) Uani 1 1 d . . . . .
H6BA H 0.943861 0.681844 0.739224 0.114 Uiso 1 1 calc R U . . .
H6BB H 0.877085 0.704463 0.756949 0.114 Uiso 1 1 calc R U . . .
H6BC H 0.913349 1.026167 0.746083 0.114 Uiso 1 1 calc R U . . .
C7B C 0.7932(4) 0.9436(19) 0.5872(2) 0.0521(18) Uani 1 1 d . . . . .
H7B H 0.758751 1.070246 0.592158 0.063 Uiso 1 1 calc R U . . .
C8B C 0.8055(4) 0.845(2) 0.5445(3) 0.0541(19) Uani 1 1 d . . . . .
H8B H 0.840840 0.723108 0.540925 0.065 Uiso 1 1 calc R U . . .
C9B C 0.7715(3) 0.9029(19) 0.5042(2) 0.0450(17) Uani 1 1 d . . . . .
C10B C 0.7902(5) 0.786(2) 0.4628(4) 0.058(3) Uani 1 1 d . . . . .
H10B H 0.826504 0.670414 0.462232 0.069 Uiso 1 1 calc R U . . .
C11B C 0.7617(4) 0.822(2) 0.4236(3) 0.056(2) Uani 1 1 d . . . . .
H11B H 0.778875 0.742961 0.397023 0.068 Uiso 1 1 calc R U . . .
C12B C 0.7050(3) 0.9824(18) 0.4225(2) 0.0465(17) Uani 1 1 d . . . . .
C13B C 0.6832(3) 1.1034(19) 0.4641(2) 0.0493(17) Uani 1 1 d . . . . .
H13B H 0.645835 1.208652 0.464843 0.059 Uiso 1 1 calc R U . . .
C14B C 0.7155(3) 1.0704(17) 0.5035(2) 0.0467(17) Uani 1 1 d . . . . .
H14B H 0.700309 1.159902 0.530144 0.056 Uiso 1 1 calc R U . . .
N15B N 0.6716(3) 1.0148(16) 0.3841(2) 0.0593(17) Uani 1 1 d . . . . .
C16B C 0.6142(4) 1.183(3) 0.3827(3) 0.061(2) Uani 1 1 d . . . . .
H16D H 0.588552 1.100751 0.406438 0.091 Uiso 1 1 calc R U . . .
H16E H 0.595186 1.145267 0.353974 0.091 Uiso 1 1 calc R U . . .
H16F H 0.620503 1.414250 0.386913 0.091 Uiso 1 1 calc R U . . .
C17B C 0.6943(4) 0.898(2) 0.3405(3) 0.069(2) Uani 1 1 d . . . . .
H17D H 0.731747 1.006299 0.333573 0.104 Uiso 1 1 calc R U . . .
H17E H 0.665119 0.945312 0.317313 0.104 Uiso 1 1 calc R U . . .
H17F H 0.700872 0.664753 0.341979 0.104 Uiso 1 1 calc R U . . .
N18B N 0.7872(3) 1.132(2) 0.6935(3) 0.0643(18) Uani 1 1 d . . . . .
O19B O 0.7942(4) 1.198(2) 0.7321(3) 0.091(3) Uani 1 1 d . . . . .
O20B O 0.7419(3) 1.2269(18) 0.6717(3) 0.079(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.371(10) . ?
C1A O5A 1.337(10) . ?
C1A C7A 1.421(10) . ?
C2A C3A 1.440(13) . ?
C2A N18A 1.429(10) . ?
C3A N4A 1.297(12) . ?
C3A C6A 1.463(16) . ?
N4A O5A 1.411(11) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.348(11) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.441(11) . ?
C9A C10A 1.424(12) . ?
C9A C14A 1.381(9) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.397(13) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.405(11) . ?
C12A C13A 1.400(9) . ?
C12A N15A 1.377(9) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.368(10) . ?
C14A H14A 0.9300 . ?
N15A C16A 1.477(12) . ?
N15A C17A 1.451(10) . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
N18A O19A 1.279(10) . ?
N18A O20A 1.194(10) . ?
C1B C2B 1.360(10) . ?
C1B O5B 1.328(10) . ?
C1B C7B 1.434(10) . ?
C2B C3B 1.424(13) . ?
C2B N18B 1.422(11) . ?
C3B N4B 1.271(13) . ?
C3B C6B 1.516(16) . ?
N4B O5B 1.444(10) . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7B H7B 0.9300 . ?
C7B C8B 1.352(11) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.428(10) . ?
C9B C10B 1.377(12) . ?
C9B C14B 1.411(10) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.327(14) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.411(12) . ?
C12B C13B 1.408(10) . ?
C12B N15B 1.360(9) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.373(10) . ?
C14B H14B 0.9300 . ?
N15B C16B 1.441(12) . ?
N15B C17B 1.462(10) . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
N18B O19B 1.182(10) . ?
N18B O20B 1.250(10) . ?

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
C2A C1A C7A 134.5(7) . . ?
O5A C1A C2A 106.4(7) . . ?
O5A C1A C7A 119.0(7) . . ?
C1A C2A C3A 106.9(7) . . ?
C1A C2A N18A 125.1(7) . . ?
N18A C2A C3A 127.9(7) . . ?
C2A C3A C6A 131.3(10) . . ?
N4A C3A C2A 109.1(9) . . ?
N4A C3A C6A 119.6(10) . . ?
C3A N4A O5A 106.5(7) . . ?
C1A O5A N4A 111.0(7) . . ?
C3A C6A H6AA 109.5 . . ?
C3A C6A H6AB 109.5 . . ?
C3A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C1A C7A H7A 119.0 . . ?
C8A C7A C1A 122.0(7) . . ?
C8A C7A H7A 119.0 . . ?
C7A C8A H8A 115.6 . . ?
C7A C8A C9A 128.8(8) . . ?
C9A C8A H8A 115.6 . . ?
C10A C9A C8A 118.4(7) . . ?
C14A C9A C8A 124.2(7) . . ?
C14A C9A C10A 117.4(7) . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A C9A 119.9(9) . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A H11A 119.5 . . ?
C10A C11A C12A 121.1(9) . . ?
C12A C11A H11A 119.5 . . ?
C13A C12A C11A 118.0(7) . . ?
N15A C12A C11A 120.0(7) . . ?
N15A C12A C13A 121.9(7) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A C12A 120.5(7) . . ?
C14A C13A H13A 119.7 . . ?
C9A C14A H14A 118.5 . . ?
C13A C14A C9A 123.0(6) . . ?
C13A C14A H14A 118.5 . . ?
C12A N15A C16A 118.9(7) . . ?
C12A N15A C17A 121.4(7) . . ?
C17A N15A C16A 119.6(8) . . ?
N15A C16A H16A 109.5 . . ?
N15A C16A H16B 109.5 . . ?
N15A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N15A C17A H17A 109.5 . . ?
N15A C17A H17B 109.5 . . ?
N15A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O19A N18A C2A 116.5(7) . . ?
O20A N18A C2A 120.9(7) . . ?
O20A N18A O19A 122.5(8) . . ?
C2B C1B C7B 135.2(8) . . ?
O5B C1B C2B 107.8(7) . . ?
O5B C1B C7B 116.8(7) . . ?
C1B C2B C3B 106.6(8) . . ?
C1B C2B N18B 127.0(7) . . ?
N18B C2B C3B 126.4(8) . . ?
C2B C3B C6B 129.3(10) . . ?
N4B C3B C2B 110.3(10) . . ?
N4B C3B C6B 120.3(10) . . ?
C3B N4B O5B 106.3(7) . . ?
C1B O5B N4B 109.0(7) . . ?
C3B C6B H6BA 109.5 . . ?
C3B C6B H6BB 109.5 . . ?
C3B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C1B C7B H7B 118.4 . . ?
C8B C7B C1B 123.1(8) . . ?
C8B C7B H7B 118.4 . . ?
C7B C8B H8B 115.7 . . ?
C7B C8B C9B 128.5(8) . . ?
C9B C8B H8B 115.7 . . ?
C10B C9B C8B 121.7(8) . . ?
C10B C9B C14B 114.6(7) . . ?
C14B C9B C8B 123.6(6) . . ?
C9B C10B H10B 116.7 . . ?
C11B C10B C9B 126.5(9) . . ?
C11B C10B H10B 116.7 . . ?
C10B C11B H11B 120.3 . . ?
C10B C11B C12B 119.5(9) . . ?
C12B C11B H11B 120.3 . . ?
C13B C12B C11B 116.4(7) . . ?
N15B C12B C11B 123.0(7) . . ?
N15B C12B C13B 120.6(7) . . ?
C12B C13B H13B 119.1 . . ?
C14B C13B C12B 121.9(7) . . ?
C14B C13B H13B 119.1 . . ?
C9B C14B H14B 119.5 . . ?
C13B C14B C9B 121.0(6) . . ?
C13B C14B H14B 119.5 . . ?
C12B N15B C16B 123.1(7) . . ?
C12B N15B C17B 121.2(7) . . ?
C16B N15B C17B 115.6(7) . . ?
N15B C16B H16D 109.5 . . ?
N15B C16B H16E 109.5 . . ?
N15B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N15B C17B H17D 109.5 . . ?
N15B C17B H17E 109.5 . . ?
N15B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O19B N18B C2B 120.5(8) . . ?
O19B N18B O20B 122.1(9) . . ?
O20B N18B C2B 117.4(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11A H11A O5B 0.93 2.78 3.462(11) 131.0 3_455 yes
C16A H16B O20B 0.96 2.75 3.414(13) 126.7 1_545 yes
C6B H6BB O19B 0.96 2.85 3.495(15) 125.3 1_545 yes
C11B H11B O5A 0.93 2.74 3.450(11) 133.7 3 yes
C16B H16E O20A 0.96 2.68 3.428(13) 135.0 . yes

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
C1A C2A C3A N4A -3.8(10) . . . . ?
C1A C2A C3A C6A 177.0(10) . . . . ?
C1A C2A N18A O19A -172.2(8) . . . . ?
C1A C2A N18A O20A 8.2(14) . . . . ?
C1A C7A C8A C9A 179.6(8) . . . . ?
C2A C1A O5A N4A -1.0(10) . . . . ?
C2A C1A C7A C8A 179.0(10) . . . . ?
C2A C3A N4A O5A 3.1(10) . . . . ?
C3A C2A N18A O19A 3.3(13) . . . . ?
C3A C2A N18A O20A -176.3(9) . . . . ?
C3A N4A O5A C1A -1.4(11) . . . . ?
O5A C1A C2A C3A 2.8(9) . . . . ?
O5A C1A C2A N18A 179.0(7) . . . . ?
O5A C1A C7A C8A -3.8(12) . . . . ?
C6A C3A N4A O5A -177.5(9) . . . . ?
C7A C1A C2A C3A -179.8(9) . . . . ?
C7A C1A C2A N18A -3.5(15) . . . . ?
C7A C1A O5A N4A -178.9(7) . . . . ?
C7A C8A C9A C10A 178.3(9) . . . . ?
C7A C8A C9A C14A -2.4(14) . . . . ?
C8A C9A C10A C11A 176.9(8) . . . . ?
C8A C9A C14A C13A -178.3(8) . . . . ?
C9A C10A C11A C12A 1.9(14) . . . . ?
C10A C9A C14A C13A 1.1(11) . . . . ?
C10A C11A C12A C13A 0.2(13) . . . . ?
C10A C11A C12A N15A -179.9(8) . . . . ?
C11A C12A C13A C14A -1.7(11) . . . . ?
C11A C12A N15A C16A 179.7(8) . . . . ?
C11A C12A N15A C17A -2.5(12) . . . . ?
C12A C13A C14A C9A 1.0(11) . . . . ?
C13A C12A N15A C16A -0.4(10) . . . . ?
C13A C12A N15A C17A 177.4(8) . . . . ?
C14A C9A C10A C11A -2.5(12) . . . . ?
N15A C12A C13A C14A 178.4(7) . . . . ?
N18A C2A C3A N4A -179.9(8) . . . . ?
N18A C2A C3A C6A 0.8(15) . . . . ?
C1B C2B C3B N4B 3.3(10) . . . . ?
C1B C2B C3B C6B 179.8(10) . . . . ?
C1B C2B N18B O19B -176.7(10) . . . . ?
C1B C2B N18B O20B 2.0(13) . . . . ?
C1B C7B C8B C9B 178.5(8) . . . . ?
C2B C1B O5B N4B 1.2(10) . . . . ?
C2B C1B C7B C8B 174.8(10) . . . . ?
C2B C3B N4B O5B -2.4(10) . . . . ?
C3B C2B N18B O19B 6.1(13) . . . . ?
C3B C2B N18B O20B -175.1(9) . . . . ?
C3B N4B O5B C1B 0.8(10) . . . . ?
O5B C1B C2B C3B -2.6(10) . . . . ?
O5B C1B C2B N18B 179.7(7) . . . . ?
O5B C1B C7B C8B 1.4(13) . . . . ?
C6B C3B N4B O5B -179.3(9) . . . . ?
C7B C1B C2B C3B -176.5(9) . . . . ?
C7B C1B C2B N18B 5.9(15) . . . . ?
C7B C1B O5B N4B 176.4(7) . . . . ?
C7B C8B C9B C10B 179.8(9) . . . . ?
C7B C8B C9B C14B -2.8(14) . . . . ?
C8B C9B C10B C11B 179.0(9) . . . . ?
C8B C9B C14B C13B -176.4(8) . . . . ?
C9B C10B C11B C12B -2.9(17) . . . . ?
C10B C9B C14B C13B 1.2(10) . . . . ?
C10B C11B C12B C13B 1.8(13) . . . . ?
C10B C11B C12B N15B -176.7(8) . . . . ?
C11B C12B C13B C14B 0.6(11) . . . . ?
C11B C12B N15B C16B -178.9(8) . . . . ?
C11B C12B N15B C17B -3.1(12) . . . . ?
C12B C13B C14B C9B -2.1(11) . . . . ?
C13B C12B N15B C16B 2.6(11) . . . . ?
C13B C12B N15B C17B 178.5(8) . . . . ?
C14B C9B C10B C11B 1.4(14) . . . . ?
N15B C12B C13B C14B 179.1(7) . . . . ?
N18B C2B C3B N4B -179.1(8) . . . . ?
N18B C2B C3B C6B -2.6(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
