# 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 2023

####################################################################### 
# 
# 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_gr-59_st
_database_code_depnum_ccdc_archive 'CCDC 2238330'
loop_
_audit_author_name
_audit_author_address
'Sofia Vorobyeva'
;Nikolaev Institute of Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-01-27 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N4 O'
_chemical_formula_sum            'C16 H16 N4 O'
_chemical_formula_weight         280.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.0005(5)
_cell_length_b                   5.2660(2)
_cell_length_c                   18.7118(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.3110(10)
_cell_angle_gamma                90
_cell_volume                     1357.44(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4611
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17280
_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         30.521
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      150.0
_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_measurement_details      
;
Data collection was performed by Dr. A. Sukhikh in XRD Facility of NIIC SB RAS.
;
_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                2546
_reflns_number_total             4138
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.042
_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)+(0.0684P)²+0.2930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1648
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C10(H10), C3(H3), C4(H4), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57746(9) 0.9764(2) 0.30193(8) 0.0326(3) Uani 1 1 d . . . . .
H1 H 0.560528 0.852757 0.322058 0.049 Uiso 1 1 calc R U . . .
N2 N 0.75816(10) 0.5079(3) 0.48954(8) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.78653(10) 0.1808(3) 0.57892(8) 0.0228(3) Uani 1 1 d . . . . .
N4 N 0.74913(10) -0.0079(3) 0.61041(9) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.59859(10) 0.6011(3) 0.39670(8) 0.0251(3) Uani 1 1 d . . . . .
C11 C 0.72141(12) 0.3202(3) 0.51628(10) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.88630(12) 0.1991(3) 0.61653(10) 0.0232(4) Uani 1 1 d . . . . .
C7 C 0.69531(12) 0.6416(3) 0.42987(10) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.83519(12) 0.8913(3) 0.42860(11) 0.0261(4) Uani 1 1 d . . . . .
H5 H 0.876423 0.787209 0.469929 0.031 Uiso 1 1 calc R U . . .
C1 C 0.67496(13) 1.0047(3) 0.33641(10) 0.0256(4) Uani 1 1 d . . . . .
C15 C 0.82554(13) -0.1062(3) 0.66700(10) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.73486(12) 0.8483(3) 0.39790(10) 0.0225(4) Uani 1 1 d . . . . .
C14 C 0.91217(13) 0.0169(3) 0.67305(10) 0.0256(4) Uani 1 1 d . . . . .
H14 H 0.976008 -0.020185 0.709435 0.031 Uiso 1 1 calc R U . . .
C13 C 0.94949(12) 0.3827(3) 0.59865(11) 0.0281(4) Uani 1 1 d . . . . .
H13A H 0.942873 0.358548 0.544846 0.042 Uiso 1 1 calc R U . . .
H13B H 1.017204 0.354878 0.634144 0.042 Uiso 1 1 calc R U . . .
H13C H 0.930185 0.556142 0.605126 0.042 Uiso 1 1 calc R U . . .
C8 C 0.56305(12) 0.4063(3) 0.42450(10) 0.0260(4) Uani 1 1 d . . . . .
C10 C 0.62287(12) 0.2589(3) 0.48487(10) 0.0264(4) Uani 1 1 d . . . . .
H10 H 0.598292 0.121217 0.504429 0.032 Uiso 1 1 calc R U . . .
C3 C 0.81519(14) 1.2349(3) 0.33978(10) 0.0298(4) Uani 1 1 d . . . . .
H3 H 0.842533 1.366036 0.319994 0.036 Uiso 1 1 calc R U . . .
C4 C 0.87548(13) 1.0811(4) 0.40021(11) 0.0291(4) Uani 1 1 d . . . . .
H4 H 0.943734 1.106926 0.421654 0.035 Uiso 1 1 calc R U . . .
C16 C 0.81462(14) -0.3209(4) 0.71509(11) 0.0308(4) Uani 1 1 d . . . . .
H16A H 0.810682 -0.253721 0.762589 0.046 Uiso 1 1 calc R U . . .
H16B H 0.870786 -0.434300 0.728989 0.046 Uiso 1 1 calc R U . . .
H16C H 0.755239 -0.415630 0.685233 0.046 Uiso 1 1 calc R U . . .
C2 C 0.71624(14) 1.1979(3) 0.30858(11) 0.0295(4) Uani 1 1 d . . . . .
H2 H 0.675764 1.304929 0.267764 0.035 Uiso 1 1 calc R U . . .
C9 C 0.45589(13) 0.3614(4) 0.38519(11) 0.0342(4) Uani 1 1 d . . . . .
H9A H 0.421093 0.516863 0.387279 0.051 Uiso 1 1 calc R U . . .
H9B H 0.437273 0.223939 0.411826 0.051 Uiso 1 1 calc R U . . .
H9C H 0.439223 0.313975 0.330772 0.051 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
O1 H1 0.8400 . ?
O1 C1 1.353(2) . ?
N2 C11 1.323(2) . ?
N2 C7 1.341(2) . ?
N3 N4 1.3820(19) . ?
N3 C11 1.400(2) . ?
N3 C12 1.382(2) . ?
N4 C15 1.320(2) . ?
N1 C7 1.350(2) . ?
N1 C8 1.351(2) . ?
C11 C10 1.395(2) . ?
C12 C14 1.366(2) . ?
C12 C13 1.482(2) . ?
C7 C6 1.475(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C4 1.379(3) . ?
C1 C6 1.411(2) . ?
C1 C2 1.395(3) . ?
C15 C14 1.416(2) . ?
C15 C16 1.494(2) . ?
C14 H14 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 C10 1.372(2) . ?
C8 C9 1.498(2) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C3 C2 1.377(3) . ?
C4 H4 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C2 H2 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 O1 H1 109.5 . . ?
C11 N2 C7 116.52(15) . . ?
N4 N3 C11 117.86(14) . . ?
N4 N3 C12 111.94(13) . . ?
C12 N3 C11 130.20(15) . . ?
C15 N4 N3 104.71(14) . . ?
C7 N1 C8 117.31(15) . . ?
N2 C11 N3 116.83(15) . . ?
N2 C11 C10 122.97(16) . . ?
C10 C11 N3 120.20(16) . . ?
N3 C12 C13 126.23(15) . . ?
C14 C12 N3 105.29(15) . . ?
C14 C12 C13 128.47(16) . . ?
N2 C7 N1 124.97(16) . . ?
N2 C7 C6 117.53(15) . . ?
N1 C7 C6 117.50(15) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.52(17) . . ?
O1 C1 C6 122.93(16) . . ?
O1 C1 C2 117.29(16) . . ?
C2 C1 C6 119.78(16) . . ?
N4 C15 C14 111.25(16) . . ?
N4 C15 C16 120.86(16) . . ?
C14 C15 C16 127.89(16) . . ?
C5 C6 C7 119.49(15) . . ?
C5 C6 C1 118.31(16) . . ?
C1 C6 C7 122.20(15) . . ?
C12 C14 C15 106.81(15) . . ?
C12 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C8 C10 121.16(15) . . ?
N1 C8 C9 116.16(16) . . ?
C10 C8 C9 122.68(16) . . ?
C11 C10 H10 121.5 . . ?
C8 C10 C11 117.04(16) . . ?
C8 C10 H10 121.5 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.42(17) . . ?
C5 C4 C3 119.41(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.55(17) . . ?
C3 C2 H2 119.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C1 C6 C7 -0.5(3) . . . . ?
O1 C1 C6 C5 178.95(16) . . . . ?
O1 C1 C2 C3 -178.71(16) . . . . ?
N2 C11 C10 C8 -1.2(3) . . . . ?
N2 C7 C6 C5 2.2(2) . . . . ?
N2 C7 C6 C1 -178.43(15) . . . . ?
N3 N4 C15 C14 0.32(19) . . . . ?
N3 N4 C15 C16 -179.38(15) . . . . ?
N3 C11 C10 C8 178.90(16) . . . . ?
N3 C12 C14 C15 0.12(19) . . . . ?
N4 N3 C11 N2 176.78(14) . . . . ?
N4 N3 C11 C10 -3.3(2) . . . . ?
N4 N3 C12 C14 0.07(19) . . . . ?
N4 N3 C12 C13 -179.05(16) . . . . ?
N4 C15 C14 C12 -0.3(2) . . . . ?
N1 C7 C6 C5 -177.69(15) . . . . ?
N1 C7 C6 C1 1.7(2) . . . . ?
N1 C8 C10 C11 0.4(3) . . . . ?
C11 N2 C7 N1 1.1(2) . . . . ?
C11 N2 C7 C6 -178.69(15) . . . . ?
C11 N3 N4 C15 179.68(14) . . . . ?
C11 N3 C12 C14 -179.85(16) . . . . ?
C11 N3 C12 C13 1.0(3) . . . . ?
C12 N3 N4 C15 -0.25(18) . . . . ?
C12 N3 C11 N2 -3.3(3) . . . . ?
C12 N3 C11 C10 176.62(17) . . . . ?
C7 N2 C11 N3 -179.61(14) . . . . ?
C7 N2 C11 C10 0.5(2) . . . . ?
C7 N1 C8 C10 1.1(3) . . . . ?
C7 N1 C8 C9 -178.41(16) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C13 C12 C14 C15 179.21(17) . . . . ?
C8 N1 C7 N2 -1.9(3) . . . . ?
C8 N1 C7 C6 177.91(15) . . . . ?
C4 C5 C6 C7 179.57(16) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C16 C15 C14 C12 179.38(17) . . . . ?
C2 C1 C6 C7 179.81(16) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C9 C8 C10 C11 179.81(17) . . . . ?

_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_bch_l60
_database_code_depnum_ccdc_archive 'CCDC 2238332'
loop_
_audit_author_name
_audit_author_address
'Sofia Vorobyeva'
;Nikolaev Institute of Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-01-27 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 N4 O'
_chemical_formula_sum            'C26 H20 N4 O'
_chemical_formula_weight         404.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0306(9)
_cell_length_b                   10.1285(9)
_cell_length_c                   12.2622(10)
_cell_angle_alpha                94.126(3)
_cell_angle_beta                 113.697(3)
_cell_angle_gamma                109.740(3)
_cell_volume                     1042.06(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    250.0
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.9333.
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    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         1.869
_diffrn_ambient_temperature      250.0
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2924
_reflns_number_total             4276
_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 SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0451
_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)+(0.0704P)²+0.0829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1327
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C19(H19), C6(H6), C22(H22), C18(H18), C15(H15), C16(H16),
 C17(H17), C5(H5), C3(H3), C23(H23), C4(H4), C26(H26), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
N2 N 0.27737(14) 0.49381(13) 0.70608(11) 0.0428(3) Uani 1 1 d . . . . .
O1 O 0.10177(17) 0.78577(15) 0.52302(11) 0.0676(4) Uani 1 1 d . . . . .
H1 H 0.131395 0.728619 0.497216 0.101 Uiso 1 1 calc R U . . .
N3 N 0.35588(15) 0.30194(14) 0.71399(11) 0.0433(3) Uani 1 1 d . . . . .
N1 N 0.21100(15) 0.58760(14) 0.52804(11) 0.0454(3) Uani 1 1 d . . . . .
N4 N 0.43211(15) 0.23497(14) 0.67430(11) 0.0463(3) Uani 1 1 d . . . . .
C11 C 0.30834(17) 0.40037(16) 0.64930(13) 0.0408(3) Uani 1 1 d . . . . .
C7 C 0.22777(17) 0.58441(16) 0.64198(13) 0.0416(4) Uani 1 1 d . . . . .
C20 C 0.47727(18) 0.16038(16) 0.75616(13) 0.0433(4) Uani 1 1 d . . . . .
C13 C 0.26990(18) 0.31171(16) 0.88287(13) 0.0418(4) Uani 1 1 d . . . . .
C8 C 0.24805(18) 0.49442(17) 0.47399(13) 0.0452(4) Uani 1 1 d . . . . .
C12 C 0.35349(17) 0.26867(16) 0.82089(13) 0.0419(4) Uani 1 1 d . . . . .
C1 C 0.18874(17) 0.68759(17) 0.70131(14) 0.0445(4) Uani 1 1 d . . . . .
C10 C 0.29772(18) 0.39707(17) 0.53272(13) 0.0461(4) Uani 1 1 d . . . . .
H10 H 0.323354 0.331231 0.495651 0.055 Uiso 1 1 calc R U . . .
C21 C 0.56115(18) 0.07111(17) 0.74163(14) 0.0469(4) Uani 1 1 d . . . . .
C14 C 0.35159(19) 0.37583(17) 1.00752(14) 0.0471(4) Uani 1 1 d . . . . .
H14 H 0.459786 0.393563 1.050869 0.056 Uiso 1 1 calc R U . . .
C19 C 0.43152(18) 0.17987(17) 0.84900(14) 0.0460(4) Uani 1 1 d . . . . .
H19 H 0.451344 0.139090 0.917332 0.055 Uiso 1 1 calc R U . . .
C6 C 0.21138(19) 0.69269(18) 0.82212(15) 0.0509(4) Uani 1 1 d . . . . .
H6 H 0.251198 0.629860 0.864159 0.061 Uiso 1 1 calc R U . . .
C22 C 0.6161(2) 0.07900(19) 0.65360(15) 0.0541(4) Uani 1 1 d . . . . .
H22 H 0.599100 0.142136 0.601986 0.065 Uiso 1 1 calc R U . . .
C18 C 0.10812(19) 0.28119(19) 0.82124(15) 0.0524(4) Uani 1 1 d . . . . .
H18 H 0.050357 0.236646 0.736894 0.063 Uiso 1 1 calc R U . . .
C2 C 0.12865(19) 0.78225(18) 0.63990(16) 0.0519(4) Uani 1 1 d . . . . .
C15 C 0.2757(2) 0.41397(19) 1.06874(15) 0.0538(4) Uani 1 1 d . . . . .
H15 H 0.333303 0.460282 1.152729 0.065 Uiso 1 1 calc R U . . .
C16 C 0.1168(2) 0.38450(19) 1.00744(16) 0.0564(4) Uani 1 1 d . . . . .
H16 H 0.065238 0.410505 1.049114 0.068 Uiso 1 1 calc R U . . .
C9 C 0.2306(2) 0.5008(2) 0.34776(14) 0.0573(4) Uani 1 1 d . . . . .
H9A H 0.136238 0.517822 0.301260 0.086 Uiso 1 1 calc R U . . .
H9B H 0.220875 0.409955 0.306962 0.086 Uiso 1 1 calc R U . . .
H9C H 0.323345 0.578871 0.353166 0.086 Uiso 1 1 calc R U . . .
C17 C 0.0329(2) 0.3163(2) 0.88401(17) 0.0598(5) Uani 1 1 d . . . . .
H17 H -0.076707 0.293707 0.842421 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1765(2) 0.7878(2) 0.88062(17) 0.0605(5) Uani 1 1 d . . . . .
H5 H 0.193440 0.790520 0.962062 0.073 Uiso 1 1 calc R U . . .
C3 C 0.0918(2) 0.87637(19) 0.69981(18) 0.0627(5) Uani 1 1 d . . . . .
H3 H 0.049650 0.938416 0.658484 0.075 Uiso 1 1 calc R U . . .
C23 C 0.6949(2) -0.0045(2) 0.64113(17) 0.0647(5) Uani 1 1 d . . . . .
H23 H 0.730905 0.001700 0.581003 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1165(2) 0.8793(2) 0.81864(19) 0.0669(5) Uani 1 1 d . . . . .
H4 H 0.092271 0.944229 0.858257 0.080 Uiso 1 1 calc R U . . .
C26 C 0.5867(2) -0.0232(2) 0.81558(18) 0.0665(5) Uani 1 1 d . . . . .
H26 H 0.549057 -0.031462 0.874737 0.080 Uiso 1 1 calc R U . . .
C24 C 0.7211(3) -0.0965(2) 0.71601(19) 0.0740(6) Uani 1 1 d . . . . .
H24 H 0.775446 -0.153107 0.707758 0.089 Uiso 1 1 calc R U . . .
C25 C 0.6673(3) -0.1056(2) 0.8032(2) 0.0841(7) Uani 1 1 d . . . . .
H25 H 0.685578 -0.168404 0.854971 0.101 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
N2 C11 1.3246(18) . ?
N2 C7 1.3436(19) . ?
O1 H1 0.8300 . ?
O1 C2 1.353(2) . ?
N3 N4 1.3725(16) . ?
N3 C11 1.4077(19) . ?
N3 C12 1.3842(18) . ?
N1 C7 1.3426(18) . ?
N1 C8 1.3466(19) . ?
N4 C20 1.3259(19) . ?
C11 C10 1.3872(19) . ?
C7 C1 1.473(2) . ?
C20 C21 1.473(2) . ?
C20 C19 1.412(2) . ?
C13 C12 1.477(2) . ?
C13 C14 1.386(2) . ?
C13 C18 1.394(2) . ?
C8 C10 1.373(2) . ?
C8 C9 1.495(2) . ?
C12 C19 1.358(2) . ?
C1 C6 1.400(2) . ?
C1 C2 1.407(2) . ?
C10 H10 0.9400 . ?
C21 C22 1.391(2) . ?
C21 C26 1.380(2) . ?
C14 H14 0.9400 . ?
C14 C15 1.381(2) . ?
C19 H19 0.9400 . ?
C6 H6 0.9400 . ?
C6 C5 1.377(2) . ?
C22 H22 0.9400 . ?
C22 C23 1.376(2) . ?
C18 H18 0.9400 . ?
C18 C17 1.377(2) . ?
C2 C3 1.393(2) . ?
C15 H15 0.9400 . ?
C15 C16 1.370(2) . ?
C16 H16 0.9400 . ?
C16 C17 1.382(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C17 H17 0.9400 . ?
C5 H5 0.9400 . ?
C5 C4 1.382(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.373(3) . ?
C23 H23 0.9400 . ?
C23 C24 1.370(3) . ?
C4 H4 0.9400 . ?
C26 H26 0.9400 . ?
C26 C25 1.382(3) . ?
C24 H24 0.9400 . ?
C24 C25 1.374(3) . ?
C25 H25 0.9400 . ?

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 N2 C7 115.98(13) . . ?
C2 O1 H1 109.5 . . ?
N4 N3 C11 116.93(11) . . ?
N4 N3 C12 111.67(12) . . ?
C12 N3 C11 131.08(12) . . ?
C7 N1 C8 117.90(13) . . ?
C20 N4 N3 105.03(12) . . ?
N2 C11 N3 116.60(12) . . ?
N2 C11 C10 123.46(14) . . ?
C10 C11 N3 119.94(13) . . ?
N2 C7 C1 117.42(13) . . ?
N1 C7 N2 124.85(14) . . ?
N1 C7 C1 117.73(14) . . ?
N4 C20 C21 120.36(13) . . ?
N4 C20 C19 110.77(13) . . ?
C19 C20 C21 128.86(14) . . ?
C14 C13 C12 119.32(14) . . ?
C14 C13 C18 118.75(14) . . ?
C18 C13 C12 121.80(13) . . ?
N1 C8 C10 120.85(14) . . ?
N1 C8 C9 117.14(14) . . ?
C10 C8 C9 122.01(14) . . ?
N3 C12 C13 126.07(13) . . ?
C19 C12 N3 105.50(13) . . ?
C19 C12 C13 128.22(13) . . ?
C6 C1 C7 119.71(14) . . ?
C6 C1 C2 118.44(15) . . ?
C2 C1 C7 121.85(14) . . ?
C11 C10 H10 121.5 . . ?
C8 C10 C11 116.92(14) . . ?
C8 C10 H10 121.5 . . ?
C22 C21 C20 121.29(14) . . ?
C26 C21 C20 120.34(15) . . ?
C26 C21 C22 118.36(16) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.72(15) . . ?
C15 C14 H14 119.6 . . ?
C20 C19 H19 126.5 . . ?
C12 C19 C20 107.03(13) . . ?
C12 C19 H19 126.5 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.35(17) . . ?
C5 C6 H6 119.3 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.82(17) . . ?
C23 C22 H22 119.6 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 119.96(15) . . ?
C17 C18 H18 120.0 . . ?
O1 C2 C1 123.21(15) . . ?
O1 C2 C3 117.31(16) . . ?
C3 C2 C1 119.48(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.21(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.60(15) . . ?
C17 C16 H16 120.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C18 C17 C16 120.71(16) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.46(18) . . ?
C4 C5 H5 120.3 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.60(18) . . ?
C4 C3 H3 119.7 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.25(18) . . ?
C24 C23 H23 119.9 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.65(17) . . ?
C3 C4 H4 119.7 . . ?
C21 C26 H26 119.8 . . ?
C21 C26 C25 120.43(18) . . ?
C25 C26 H26 119.8 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.59(18) . . ?
C25 C24 H24 120.2 . . ?
C26 C25 H25 119.7 . . ?
C24 C25 C26 120.54(19) . . ?
C24 C25 H25 119.7 . . ?

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
N2 C11 C10 C8 -1.8(2) . . . . ?
N2 C7 C1 C6 3.0(2) . . . . ?
N2 C7 C1 C2 -176.93(14) . . . . ?
O1 C2 C3 C4 -179.74(16) . . . . ?
N3 N4 C20 C21 178.73(13) . . . . ?
N3 N4 C20 C19 -0.45(16) . . . . ?
N3 C11 C10 C8 178.92(13) . . . . ?
N3 C12 C19 C20 -0.81(17) . . . . ?
N1 C7 C1 C6 -177.08(13) . . . . ?
N1 C7 C1 C2 3.0(2) . . . . ?
N1 C8 C10 C11 -0.3(2) . . . . ?
N4 N3 C11 N2 -161.31(12) . . . . ?
N4 N3 C11 C10 18.0(2) . . . . ?
N4 N3 C12 C13 -174.47(14) . . . . ?
N4 N3 C12 C19 0.58(17) . . . . ?
N4 C20 C21 C22 9.7(2) . . . . ?
N4 C20 C21 C26 -170.12(16) . . . . ?
N4 C20 C19 C12 0.82(18) . . . . ?
C11 N2 C7 N1 -1.3(2) . . . . ?
C11 N2 C7 C1 178.64(13) . . . . ?
C11 N3 N4 C20 174.12(12) . . . . ?
C11 N3 C12 C13 12.4(2) . . . . ?
C11 N3 C12 C19 -172.55(15) . . . . ?
C7 N2 C11 N3 -178.17(12) . . . . ?
C7 N2 C11 C10 2.6(2) . . . . ?
C7 N1 C8 C10 1.5(2) . . . . ?
C7 N1 C8 C9 -179.24(14) . . . . ?
C7 C1 C6 C5 179.88(14) . . . . ?
C7 C1 C2 O1 0.2(2) . . . . ?
C7 C1 C2 C3 179.17(14) . . . . ?
C20 C21 C22 C23 179.73(15) . . . . ?
C20 C21 C26 C25 -179.10(17) . . . . ?
C13 C12 C19 C20 174.09(15) . . . . ?
C13 C14 C15 C16 2.1(2) . . . . ?
C13 C18 C17 C16 1.3(3) . . . . ?
C8 N1 C7 N2 -0.7(2) . . . . ?
C8 N1 C7 C1 179.36(13) . . . . ?
C12 N3 N4 C20 -0.08(16) . . . . ?
C12 N3 C11 N2 11.5(2) . . . . ?
C12 N3 C11 C10 -169.18(15) . . . . ?
C12 C13 C14 C15 -178.35(14) . . . . ?
C12 C13 C18 C17 176.54(15) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C21 C20 C19 C12 -178.27(15) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C21 C26 C25 C24 -1.0(3) . . . . ?
C14 C13 C12 N3 -130.03(16) . . . . ?
C14 C13 C12 C19 56.1(2) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C19 C20 C21 C22 -171.28(16) . . . . ?
C19 C20 C21 C26 8.9(3) . . . . ?
C6 C1 C2 O1 -179.73(15) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C22 C21 C26 C25 1.1(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C18 C13 C12 N3 54.2(2) . . . . ?
C18 C13 C12 C19 -119.69(19) . . . . ?
C18 C13 C14 C15 -2.5(2) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C9 C8 C10 C11 -179.52(15) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
