# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_a
_database_code_depnum_ccdc_archive 'CCDC 2106841'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2021-10-15 downloaded from the CCDC.
;
_audit_creation_date             2020-10-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
miquel.barcelo@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl N3 O2'
_chemical_formula_sum            'C14 H14 Cl N3 O2'
_chemical_formula_weight         291.73
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   10.9144(5)
_cell_length_b                   8.5835(4)
_cell_length_c                   15.5150(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.152(2)
_cell_angle_gamma                90
_cell_volume                     1426.06(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      72.188
_cell_measurement_theta_min      4.566
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.389
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1165 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.6813.
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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16820
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         4.566
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_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                2260
_reflns_number_total             2462
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.029
_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)+(0.0723P)²+0.5573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C6(H6), C19(H19), C15(H15), C5(H5), C4(H4), C18(H18), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl20 Cl 0.29354(9) -0.16741(11) 0.38418(5) 0.1139(4) Uani 1 1 d . . . . .
O13 O 0.55613(18) 0.4016(2) 0.11701(10) 0.0814(6) Uani 1 1 d . . . . .
N1 N 0.91163(15) 0.71019(19) 0.50934(10) 0.0516(4) Uani 1 1 d . . . . .
O12 O 0.71207(15) 0.2841(2) 0.20401(10) 0.0803(5) Uani 1 1 d . . . . .
N7 N 0.72183(15) 0.6122(2) 0.44304(10) 0.0553(4) Uani 1 1 d . . . . .
H7 H 0.720609 0.685221 0.404921 0.066 Uiso 1 1 calc R U . . .
N3 N 0.81922(16) 0.5008(2) 0.57462(10) 0.0567(4) Uani 1 1 d . . . . .
C2 C 0.82012(17) 0.6061(2) 0.51089(11) 0.0457(4) Uani 1 1 d . . . . .
C10 C 0.5923(2) 0.4703(2) 0.26603(12) 0.0536(5) Uani 1 1 d . . . . .
H10A H 0.503799 0.494028 0.252301 0.064 Uiso 1 1 calc R U . . .
H10B H 0.637559 0.568134 0.269719 0.064 Uiso 1 1 calc R U . . .
C11 C 0.62557(18) 0.3743(2) 0.19299(12) 0.0503(5) Uani 1 1 d . . . . .
C9 C 0.62252(17) 0.3885(2) 0.35547(12) 0.0482(4) Uani 1 1 d . . . . .
H9 H 0.708106 0.348730 0.363024 0.058 Uiso 1 1 calc R U . . .
C14 C 0.53733(17) 0.2502(2) 0.36058(11) 0.0480(4) Uani 1 1 d . . . . .
C8 C 0.61838(18) 0.5036(2) 0.43047(12) 0.0534(5) Uani 1 1 d . . . . .
H8A H 0.540564 0.561270 0.417754 0.064 Uiso 1 1 calc R U . . .
H8B H 0.620149 0.445870 0.484455 0.064 Uiso 1 1 calc R U . . .
C6 C 1.0072(2) 0.7090(3) 0.57750(13) 0.0611(5) Uani 1 1 d . . . . .
H6 H 1.071779 0.779994 0.578295 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5869(2) 0.1031(3) 0.37828(15) 0.0624(5) Uani 1 1 d . . . . .
H19 H 0.672869 0.089583 0.385542 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4090(2) 0.2659(3) 0.35042(15) 0.0628(6) Uani 1 1 d . . . . .
H15 H 0.373053 0.363711 0.338736 0.075 Uiso 1 1 calc R U . . .
C5 C 1.0141(2) 0.6075(3) 0.64626(14) 0.0662(6) Uani 1 1 d . . . . .
H5 H 1.080839 0.608293 0.693718 0.079 Uiso 1 1 calc R U . . .
C4 C 0.9170(2) 0.5048(3) 0.64105(14) 0.0628(6) Uani 1 1 d . . . . .
H4 H 0.919374 0.433699 0.686548 0.075 Uiso 1 1 calc R U . . .
C18 C 0.5125(3) -0.0244(3) 0.38549(17) 0.0771(7) Uani 1 1 d . . . . .
H18 H 0.547973 -0.122485 0.397415 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3862(2) -0.0050(3) 0.37490(15) 0.0699(7) Uani 1 1 d . . . . .
C16 C 0.3330(2) 0.1388(3) 0.35730(16) 0.0730(7) Uani 1 1 d . . . . .
H16 H 0.246976 0.151137 0.350032 0.088 Uiso 1 1 calc R U . . .
H13 H 0.577(3) 0.333(5) 0.073(3) 0.126(12) Uiso 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
Cl20 C17 1.744(2) . ?
O13 C11 1.294(2) . ?
O13 H13 0.96(4) . ?
N1 C2 1.344(2) . ?
N1 C6 1.334(3) . ?
O12 C11 1.207(2) . ?
N7 H7 0.8600 . ?
N7 C2 1.351(2) . ?
N7 C8 1.448(2) . ?
N3 C2 1.341(2) . ?
N3 C4 1.333(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.501(3) . ?
C10 C9 1.533(3) . ?
C9 H9 0.9800 . ?
C9 C14 1.519(3) . ?
C9 C8 1.534(3) . ?
C14 C19 1.380(3) . ?
C14 C15 1.385(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.368(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(3) . ?
C4 H4 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.367(4) . ?
C17 C16 1.368(4) . ?
C16 H16 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
C11 O13 H13 111(2) . . ?
C6 N1 C2 116.78(17) . . ?
C2 N7 H7 117.9 . . ?
C2 N7 C8 124.11(17) . . ?
C8 N7 H7 117.9 . . ?
C4 N3 C2 115.69(17) . . ?
N1 C2 N7 116.17(16) . . ?
N3 C2 N1 124.95(17) . . ?
N3 C2 N7 118.87(17) . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C11 C10 C9 112.99(17) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
O13 C11 C10 113.80(18) . . ?
O12 C11 O13 123.34(18) . . ?
O12 C11 C10 122.80(18) . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C8 111.03(16) . . ?
C14 C9 C10 112.25(15) . . ?
C14 C9 H9 107.5 . . ?
C14 C9 C8 110.82(14) . . ?
C8 C9 H9 107.5 . . ?
C19 C14 C9 120.29(17) . . ?
C19 C14 C15 117.4(2) . . ?
C15 C14 C9 122.26(19) . . ?
N7 C8 C9 112.36(15) . . ?
N7 C8 H8A 109.1 . . ?
N7 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C6 H6 118.7 . . ?
N1 C6 C5 122.7(2) . . ?
C5 C6 H6 118.7 . . ?
C14 C19 H19 119.1 . . ?
C14 C19 C18 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C6 C5 H5 122.0 . . ?
C6 C5 C4 116.01(19) . . ?
C4 C5 H5 122.0 . . ?
N3 C4 C5 123.88(19) . . ?
N3 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.3(2) . . ?
C17 C18 H18 120.4 . . ?
C18 C17 Cl20 118.7(2) . . ?
C18 C17 C16 120.9(2) . . ?
C16 C17 Cl20 120.5(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?

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
N7 H7 O12 0.86 2.14 2.922(2) 150.3 2_655 yes
O13 H13 N1 0.96(4) 1.68(4) 2.633(2) 170(3) 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
Cl20 C17 C16 C15 179.90(17) . . . . ?
N1 C6 C5 C4 0.6(4) . . . . ?
C2 N1 C6 C5 0.2(3) . . . . ?
C2 N7 C8 C9 -106.5(2) . . . . ?
C2 N3 C4 C5 -0.2(3) . . . . ?
C10 C9 C14 C19 121.3(2) . . . . ?
C10 C9 C14 C15 -60.5(2) . . . . ?
C10 C9 C8 N7 -70.8(2) . . . . ?
C11 C10 C9 C14 -69.5(2) . . . . ?
C11 C10 C9 C8 165.79(16) . . . . ?
C9 C10 C11 O13 150.86(19) . . . . ?
C9 C10 C11 O12 -31.6(3) . . . . ?
C9 C14 C19 C18 178.4(2) . . . . ?
C9 C14 C15 C16 -178.51(19) . . . . ?
C14 C9 C8 N7 163.76(16) . . . . ?
C14 C19 C18 C17 0.0(4) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C8 N7 C2 N1 175.94(17) . . . . ?
C8 N7 C2 N3 -5.1(3) . . . . ?
C8 C9 C14 C19 -113.9(2) . . . . ?
C8 C9 C14 C15 64.3(2) . . . . ?
C6 N1 C2 N7 177.74(18) . . . . ?
C6 N1 C2 N3 -1.1(3) . . . . ?
C6 C5 C4 N3 -0.6(4) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C19 C18 C17 Cl20 179.97(19) . . . . ?
C19 C18 C17 C16 0.0(4) . . . . ?
C15 C14 C19 C18 0.2(3) . . . . ?
C4 N3 C2 N1 1.1(3) . . . . ?
C4 N3 C2 N7 -177.72(19) . . . . ?
C18 C17 C16 C15 -0.2(4) . . . . ?

_olex2_exptl_crystal_mounting_method cryoloop
_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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2106842'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2021-10-15 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
miquel.barcelo@uib.es
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   16.6291(18)
_cell_length_b                   7.1628(8)
_cell_length_c                   10.9025(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.168(4)
_cell_angle_gamma                90
_cell_volume                     1297.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8997
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      68.223
_cell_measurement_theta_min      6.731
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1658 before and 0.1036 after correction.
The Ratio of minimum to maximum transmission is 0.4398.
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    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28675
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.340
_diffrn_reflns_theta_min         6.178
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                4445
_reflns_number_total             4547
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.109
_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)+(0.1173P)²+0.0433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C8'(H8'A,H8'B), C10'(H10C,H10D), C14'(H14C,
 H14D), C15'(H15C,H15D), C16'(H16C,H16D), C17'(H17C,H17D), C18'(H18C,H18D)
3.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C4(H4), C5(H5), C6(H6), N7'(H7'), C4'(H4'), C5'(H5'), C6'(H6')
3.c Idealised tetrahedral OH refined as rotating group:
 O13(H13), O13'(H13')
;
_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
O12 O 0.20382(17) 0.3251(4) 0.2701(3) 0.0618(7) Uani 1 1 d . . . . .
O13 O 0.31093(17) 0.3723(4) 0.3932(2) 0.0605(7) Uani 1 1 d . . . . .
H13 H 0.333141 0.311358 0.340606 0.091 Uiso 1 1 calc R U . . .
N1 N 0.39846(17) 0.8226(4) 0.7386(2) 0.0445(6) Uani 1 1 d . . . . .
N3 N 0.44535(17) 0.8736(4) 0.5377(2) 0.0474(6) Uani 1 1 d . . . . .
N7 N 0.31338(16) 0.7983(4) 0.5693(2) 0.0450(6) Uani 1 1 d . . . . .
H7 H 0.276140 0.767244 0.617947 0.054 Uiso 1 1 calc R U . . .
C2 C 0.38743(18) 0.8332(4) 0.6165(3) 0.0395(6) Uani 1 1 d . . . . .
C4 C 0.5190(2) 0.8979(5) 0.5881(3) 0.0501(7) Uani 1 1 d . . . . .
H4 H 0.560813 0.924244 0.536473 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5365(2) 0.8863(5) 0.7114(4) 0.0527(8) Uani 1 1 d . . . . .
H5 H 0.588529 0.902213 0.744065 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4723(2) 0.8495(4) 0.7848(3) 0.0522(8) Uani 1 1 d . . . . .
H6 H 0.481300 0.843358 0.869402 0.063 Uiso 1 1 calc R U . . .
C8 C 0.29383(19) 0.8114(4) 0.4376(3) 0.0441(7) Uani 1 1 d . . . . .
H8A H 0.331500 0.735082 0.393860 0.053 Uiso 1 1 calc R U . . .
H8B H 0.300821 0.939704 0.411609 0.053 Uiso 1 1 calc R U . . .
C9 C 0.20799(16) 0.7490(4) 0.4016(3) 0.0371(6) Uani 1 1 d . . . . .
C10 C 0.19306(17) 0.5416(4) 0.4369(2) 0.0391(6) Uani 1 1 d . . . . .
H10A H 0.210945 0.522860 0.521700 0.047 Uiso 1 1 calc R U . . .
H10B H 0.135669 0.517198 0.431030 0.047 Uiso 1 1 calc R U . . .
C11 C 0.23519(19) 0.4027(4) 0.3579(3) 0.0412(6) Uani 1 1 d . . . . .
C14 C 0.1473(2) 0.8729(4) 0.4664(3) 0.0505(8) Uani 1 1 d . . . . .
H14A H 0.163282 1.002422 0.458227 0.061 Uiso 1 1 calc R U . . .
H14B H 0.149078 0.842751 0.553193 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0603(2) 0.8506(6) 0.4153(5) 0.0640(10) Uani 1 1 d . . . . .
H15A H 0.041079 0.726346 0.434153 0.077 Uiso 1 1 calc R U . . .
H15B H 0.025973 0.940116 0.454848 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0547(3) 0.8809(6) 0.2763(5) 0.0711(11) Uani 1 1 d . . . . .
H16A H 0.000009 0.857321 0.246068 0.085 Uiso 1 1 calc R U . . .
H16B H 0.067727 1.009652 0.257986 0.085 Uiso 1 1 calc R U . . .
C17 C 0.1118(2) 0.7525(5) 0.2117(3) 0.0557(8) Uani 1 1 d . . . . .
H17A H 0.108922 0.777859 0.124293 0.067 Uiso 1 1 calc R U . . .
H17B H 0.095930 0.623726 0.224051 0.067 Uiso 1 1 calc R U . . .
C18 C 0.19817(19) 0.7810(5) 0.2615(3) 0.0453(7) Uani 1 1 d . . . . .
H18A H 0.215030 0.907121 0.242837 0.054 Uiso 1 1 calc R U . . .
H18B H 0.233331 0.695613 0.219967 0.054 Uiso 1 1 calc R U . . .
O12' O 0.79671(16) -0.1725(4) 0.3036(3) 0.0611(7) Uani 1 1 d . . . . .
O13' O 0.68927(17) -0.1287(4) 0.4156(3) 0.0615(7) Uani 1 1 d . . . . .
H13' H 0.669066 -0.202493 0.365902 0.092 Uiso 1 1 calc R U . . .
N1' N 0.60236(17) 0.3222(4) 0.7509(2) 0.0442(6) Uani 1 1 d . . . . .
N3' N 0.55530(17) 0.3736(4) 0.5443(2) 0.0461(6) Uani 1 1 d . . . . .
N7' N 0.68731(15) 0.2972(4) 0.5908(2) 0.0451(6) Uani 1 1 d . . . . .
H7' H 0.724528 0.265526 0.643616 0.054 Uiso 1 1 calc R U . . .
C2' C 0.61247(18) 0.3330(4) 0.6295(3) 0.0390(6) Uani 1 1 d . . . . .
C4' C 0.4811(2) 0.3989(5) 0.5865(3) 0.0500(7) Uani 1 1 d . . . . .
H4' H 0.439242 0.425939 0.530274 0.060 Uiso 1 1 calc R U . . .
C5' C 0.4642(2) 0.3867(5) 0.7075(4) 0.0530(8) Uani 1 1 d . . . . .
H5' H 0.412150 0.403143 0.734039 0.064 Uiso 1 1 calc R U . . .
C6' C 0.5272(2) 0.3493(5) 0.7887(3) 0.0513(8) Uani 1 1 d . . . . .
H6' H 0.517691 0.342499 0.872108 0.062 Uiso 1 1 calc R U . . .
C8' C 0.70629(18) 0.3108(4) 0.4620(3) 0.0425(6) Uani 1 1 d . . . . .
H8'A H 0.698658 0.438963 0.435219 0.051 Uiso 1 1 calc R U . . .
H8'B H 0.668909 0.233540 0.414076 0.051 Uiso 1 1 calc R U . . .
C9' C 0.79258(17) 0.2504(4) 0.4358(3) 0.0357(6) Uani 1 1 d . . . . .
C10' C 0.80754(17) 0.0418(4) 0.4723(3) 0.0391(6) Uani 1 1 d . . . . .
H10C H 0.864958 0.017672 0.473421 0.047 Uiso 1 1 calc R U . . .
H10D H 0.789421 0.022456 0.554855 0.047 Uiso 1 1 calc R U . . .
C11' C 0.76596(18) -0.0963(4) 0.3882(3) 0.0401(6) Uani 1 1 d . . . . .
C14' C 0.80348(18) 0.2838(4) 0.2980(3) 0.0420(6) Uani 1 1 d . . . . .
H14C H 0.768858 0.198615 0.251235 0.050 Uiso 1 1 calc R U . . .
H14D H 0.786673 0.410033 0.277527 0.050 Uiso 1 1 calc R U . . .
C15' C 0.8901(2) 0.2563(5) 0.2605(3) 0.0522(8) Uani 1 1 d . . . . .
H15C H 0.905837 0.127337 0.274312 0.063 Uiso 1 1 calc R U . . .
H15D H 0.893865 0.282522 0.173580 0.063 Uiso 1 1 calc R U . . .
C16' C 0.9466(3) 0.3833(6) 0.3330(4) 0.0660(10) Uani 1 1 d . . . . .
H16C H 0.934278 0.512164 0.312576 0.079 Uiso 1 1 calc R U . . .
H16D H 1.001504 0.358584 0.310604 0.079 Uiso 1 1 calc R U . . .
C17' C 0.9397(2) 0.3548(5) 0.4711(4) 0.0564(8) Uani 1 1 d . . . . .
H17C H 0.972865 0.446443 0.514732 0.068 Uiso 1 1 calc R U . . .
H17D H 0.959813 0.231778 0.493413 0.068 Uiso 1 1 calc R U . . .
C18' C 0.85271(19) 0.3735(4) 0.5102(3) 0.0451(7) Uani 1 1 d . . . . .
H18C H 0.836326 0.502937 0.501590 0.054 Uiso 1 1 calc R U . . .
H18D H 0.850339 0.340721 0.596315 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O12 C11 1.208(4) . ?
O13 H13 0.8200 . ?
O13 C11 1.321(4) . ?
N1 C2 1.339(4) . ?
N1 C6 1.323(5) . ?
N3 C2 1.346(4) . ?
N3 C4 1.335(4) . ?
N7 H7 0.8600 . ?
N7 C2 1.340(4) . ?
N7 C8 1.463(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(5) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.533(4) . ?
C9 C10 1.557(4) . ?
C9 C14 1.536(4) . ?
C9 C18 1.547(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.539(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.531(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.530(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O12' C11' 1.202(4) . ?
O13' H13' 0.8200 . ?
O13' C11' 1.341(4) . ?
N1' C2' 1.343(4) . ?
N1' C6' 1.345(4) . ?
N3' C2' 1.335(4) . ?
N3' C4' 1.346(4) . ?
N7' H7' 0.8600 . ?
N7' C2' 1.354(4) . ?
N7' C8' 1.454(4) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.362(5) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.372(6) . ?
C6' H6' 0.9300 . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C9' 1.536(4) . ?
C9' C10' 1.563(4) . ?
C9' C14' 1.539(4) . ?
C9' C18' 1.541(4) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C10' C11' 1.500(4) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C14' C15' 1.525(4) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C15' C16' 1.510(6) . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?
C16' C17' 1.528(6) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C17' C18' 1.530(5) . ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?

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
C11 O13 H13 109.5 . . ?
C6 N1 C2 117.4(3) . . ?
C4 N3 C2 115.6(3) . . ?
C2 N7 H7 118.9 . . ?
C2 N7 C8 122.1(2) . . ?
C8 N7 H7 118.9 . . ?
N1 C2 N3 124.9(3) . . ?
N1 C2 N7 117.4(3) . . ?
N7 C2 N3 117.6(3) . . ?
N3 C4 H4 118.2 . . ?
N3 C4 C5 123.7(3) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.1(3) . . ?
C6 C5 H5 121.9 . . ?
N1 C6 C5 122.2(3) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N7 C8 H8A 108.8 . . ?
N7 C8 H8B 108.8 . . ?
N7 C8 C9 113.7(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C8 C9 C10 111.8(2) . . ?
C8 C9 C14 109.6(3) . . ?
C8 C9 C18 105.8(2) . . ?
C14 C9 C10 108.9(2) . . ?
C14 C9 C18 108.8(3) . . ?
C18 C9 C10 111.9(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.0(2) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O12 C11 O13 122.2(3) . . ?
O12 C11 C10 124.1(3) . . ?
O13 C11 C10 113.6(3) . . ?
C9 C14 H14A 108.9 . . ?
C9 C14 H14B 108.9 . . ?
C9 C14 C15 113.5(3) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.4(4) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 C15 111.0(3) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C18 110.6(3) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C9 C18 H18A 108.9 . . ?
C9 C18 H18B 108.9 . . ?
C17 C18 C9 113.1(3) . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.8 . . ?
C11' O13' H13' 109.5 . . ?
C2' N1' C6' 116.5(3) . . ?
C2' N3' C4' 115.5(3) . . ?
C2' N7' H7' 119.2 . . ?
C2' N7' C8' 121.6(3) . . ?
C8' N7' H7' 119.2 . . ?
N1' C2' N7' 116.6(3) . . ?
N3' C2' N1' 125.8(3) . . ?
N3' C2' N7' 117.6(3) . . ?
N3' C4' H4' 118.4 . . ?
N3' C4' C5' 123.2(3) . . ?
C5' C4' H4' 118.4 . . ?
C4' C5' H5' 121.4 . . ?
C4' C5' C6' 117.2(3) . . ?
C6' C5' H5' 121.4 . . ?
N1' C6' C5' 121.7(3) . . ?
N1' C6' H6' 119.1 . . ?
C5' C6' H6' 119.1 . . ?
N7' C8' H8'A 108.9 . . ?
N7' C8' H8'B 108.9 . . ?
N7' C8' C9' 113.5(2) . . ?
H8'A C8' H8'B 107.7 . . ?
C9' C8' H8'A 108.9 . . ?
C9' C8' H8'B 108.9 . . ?
C8' C9' C10' 111.3(2) . . ?
C8' C9' C14' 106.4(2) . . ?
C8' C9' C18' 109.5(2) . . ?
C14' C9' C10' 111.9(2) . . ?
C14' C9' C18' 109.1(2) . . ?
C18' C9' C10' 108.6(2) . . ?
C9' C10' H10C 108.7 . . ?
C9' C10' H10D 108.7 . . ?
H10C C10' H10D 107.6 . . ?
C11' C10' C9' 114.2(2) . . ?
C11' C10' H10C 108.7 . . ?
C11' C10' H10D 108.7 . . ?
O12' C11' O13' 121.9(3) . . ?
O12' C11' C10' 124.7(3) . . ?
O13' C11' C10' 113.4(2) . . ?
C9' C14' H14C 109.0 . . ?
C9' C14' H14D 109.0 . . ?
H14C C14' H14D 107.8 . . ?
C15' C14' C9' 112.9(3) . . ?
C15' C14' H14C 109.0 . . ?
C15' C14' H14D 109.0 . . ?
C14' C15' H15C 109.5 . . ?
C14' C15' H15D 109.5 . . ?
H15C C15' H15D 108.0 . . ?
C16' C15' C14' 110.9(3) . . ?
C16' C15' H15C 109.5 . . ?
C16' C15' H15D 109.5 . . ?
C15' C16' H16C 109.3 . . ?
C15' C16' H16D 109.3 . . ?
C15' C16' C17' 111.6(3) . . ?
H16C C16' H16D 108.0 . . ?
C17' C16' H16C 109.3 . . ?
C17' C16' H16D 109.3 . . ?
C16' C17' H17C 109.3 . . ?
C16' C17' H17D 109.3 . . ?
C16' C17' C18' 111.7(3) . . ?
H17C C17' H17D 107.9 . . ?
C18' C17' H17C 109.3 . . ?
C18' C17' H17D 109.3 . . ?
C9' C18' H18C 108.8 . . ?
C9' C18' H18D 108.8 . . ?
C17' C18' C9' 113.9(3) . . ?
C17' C18' H18C 108.8 . . ?
C17' C18' H18D 108.8 . . ?
H18C C18' H18D 107.7 . . ?

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
O13 H13 N1 0.82 1.85 2.664(4) 170.5 2_564 yes
O13 H13 N7 0.82 3.07 3.739(4) 141.0 2_564 yes
N7 H7 O12 0.86 2.19 3.032(4) 167.3 2_565 yes
N7 H7 O13 0.86 3.20 3.739(4) 123.5 2_565 yes
C4 H4 O13' 0.93 2.58 3.463(4) 158.6 1_565 yes
C5 H5 O13' 0.93 2.95 3.741(5) 143.9 2_565 yes
C6 H6 N3 0.93 2.81 3.439(4) 125.6 2_575 yes
C6 H6 N3' 0.93 2.72 3.489(4) 140.8 2_565 yes
C8 H8B N1 0.97 3.05 3.859(4) 141.3 2_574 yes
C10 H10A O12 0.97 2.93 3.754(4) 144.0 2_565 yes
C14 H14B O12 0.97 2.78 3.691(5) 157.6 2_565 yes
C17 H17B O12 0.97 2.82 3.471(5) 124.8 . yes
C18 H18A O12 0.97 3.01 3.899(4) 152.2 1_565 yes
O13' H13' N1' 0.82 1.85 2.653(4) 164.9 2_554 yes
O13' H13' N7' 0.82 3.10 3.741(4) 136.7 2_554 yes
N7' H7' O12' 0.86 2.18 3.029(4) 167.3 2 yes
N7' H7' O13' 0.86 3.20 3.741(4) 123.3 2 yes
C4' H4' O13 0.93 2.59 3.468(4) 158.4 . yes
C5' H5' O13 0.93 2.94 3.737(5) 144.3 2_565 yes
C6' H6' N3 0.93 2.70 3.471(4) 141.4 2_565 yes
C6' H6' N3' 0.93 2.82 3.439(4) 124.8 2_565 yes
C8' H8'A N1' 0.97 3.05 3.859(4) 142.1 2_564 yes
C10' H10D O12' 0.97 2.92 3.742(4) 143.8 2 yes
C14' H14D O12' 0.97 3.01 3.897(4) 153.0 1_565 yes
C15' H15C O12' 0.97 2.84 3.481(5) 124.6 . yes
C18' H18D O12' 0.97 2.74 3.660(4) 158.6 2 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
N3 C4 C5 C6 -0.9(6) . . . . ?
N7 C8 C9 C10 -60.3(3) . . . . ?
N7 C8 C9 C14 60.6(3) . . . . ?
N7 C8 C9 C18 177.7(3) . . . . ?
C2 N1 C6 C5 -0.3(5) . . . . ?
C2 N3 C4 C5 -0.9(5) . . . . ?
C2 N7 C8 C9 174.8(3) . . . . ?
C4 N3 C2 N1 2.3(5) . . . . ?
C4 N3 C2 N7 -176.7(3) . . . . ?
C4 C5 C6 N1 1.5(5) . . . . ?
C6 N1 C2 N3 -1.8(5) . . . . ?
C6 N1 C2 N7 177.3(3) . . . . ?
C8 N7 C2 N1 178.1(3) . . . . ?
C8 N7 C2 N3 -2.8(5) . . . . ?
C8 C9 C10 C11 -72.1(3) . . . . ?
C8 C9 C14 C15 167.4(3) . . . . ?
C8 C9 C18 C17 -171.7(3) . . . . ?
C9 C10 C11 O12 -96.3(4) . . . . ?
C9 C10 C11 O13 83.6(3) . . . . ?
C9 C14 C15 C16 -54.0(4) . . . . ?
C10 C9 C14 C15 -70.1(4) . . . . ?
C10 C9 C18 C17 66.3(3) . . . . ?
C14 C9 C10 C11 166.7(3) . . . . ?
C14 C9 C18 C17 -54.1(3) . . . . ?
C14 C15 C16 C17 55.1(4) . . . . ?
C15 C16 C17 C18 -56.7(4) . . . . ?
C16 C17 C18 C9 57.5(4) . . . . ?
C18 C9 C10 C11 46.4(3) . . . . ?
C18 C9 C14 C15 52.2(4) . . . . ?
N3' C4' C5' C6' 0.9(6) . . . . ?
N7' C8' C9' C10' 60.8(3) . . . . ?
N7' C8' C9' C14' -177.0(3) . . . . ?
N7' C8' C9' C18' -59.2(3) . . . . ?
C2' N1' C6' C5' -0.2(5) . . . . ?
C2' N3' C4' C5' 0.7(5) . . . . ?
C2' N7' C8' C9' -175.6(3) . . . . ?
C4' N3' C2' N1' -2.4(5) . . . . ?
C4' N3' C2' N7' 176.8(3) . . . . ?
C4' C5' C6' N1' -1.2(5) . . . . ?
C6' N1' C2' N3' 2.1(5) . . . . ?
C6' N1' C2' N7' -177.0(3) . . . . ?
C8' N7' C2' N1' -177.9(3) . . . . ?
C8' N7' C2' N3' 2.9(5) . . . . ?
C8' C9' C10' C11' 72.1(3) . . . . ?
C8' C9' C14' C15' 171.9(3) . . . . ?
C8' C9' C18' C17' -167.5(3) . . . . ?
C9' C10' C11' O12' 95.6(4) . . . . ?
C9' C10' C11' O13' -84.2(3) . . . . ?
C9' C14' C15' C16' -57.5(4) . . . . ?
C10' C9' C14' C15' -66.3(3) . . . . ?
C10' C9' C18' C17' 70.8(3) . . . . ?
C14' C9' C10' C11' -46.9(3) . . . . ?
C14' C9' C18' C17' -51.4(3) . . . . ?
C14' C15' C16' C17' 56.1(4) . . . . ?
C15' C16' C17' C18' -53.5(4) . . . . ?
C16' C17' C18' C9' 52.2(4) . . . . ?
C18' C9' C10' C11' -167.4(2) . . . . ?
C18' C9' C14' C15' 53.9(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'cryoloop, covered with Parabar 10320 (formerly known as Paratone)'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(3)
2 0.1(3)

