# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_global
_database_code_depnum_ccdc_archive 'CCDC 2253867'
loop_
_audit_author_name
_audit_author_address
'Artur Sikorski'
;University of Gdansk, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
to whom correspondence should be addressed
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H6 O2'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2502(8)
_cell_length_b                   9.0739(11)
_cell_length_c                   12.1019(10)
_cell_angle_alpha                100.594(9)
_cell_angle_beta                 94.574(8)
_cell_angle_gamma                95.976(10)
_cell_volume                     774.34(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4840
_cell_measurement_theta_min      3.432
_cell_measurement_theta_max      25.005

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.999

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_reflns_number            4840
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2728
_reflns_number_gt                1874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.0947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.3191(3) 0.4945(3) 1.12347(16) 0.0545(6) Uani 1 1 d . . . . .
H1 H 0.335858 0.575831 1.184072 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3563(3) 0.3581(3) 1.14070(18) 0.0629(6) Uani 1 1 d . . . . .
H2 H 0.396806 0.345613 1.212903 0.076 Uiso 1 1 calc R U . . .
C3 C 0.3341(3) 0.2336(3) 1.0498(2) 0.0638(6) Uani 1 1 d . . . . .
H3 H 0.361999 0.139966 1.062380 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2723(3) 0.2492(2) 0.94407(18) 0.0541(5) Uani 1 1 d . . . . .
H4 H 0.258686 0.166255 0.884868 0.065 Uiso 1 1 calc R U . . .
C5 C 0.0544(3) 0.5488(3) 0.68775(17) 0.0590(6) Uani 1 1 d . . . . .
H5 H 0.032208 0.462963 0.630881 0.071 Uiso 1 1 calc R U . . .
C6 C 0.0182(3) 0.6837(3) 0.66481(19) 0.0698(7) Uani 1 1 d . . . . .
H6 H -0.029243 0.689156 0.592157 0.084 Uiso 1 1 calc R U . . .
C7 C 0.0504(3) 0.8156(3) 0.7481(2) 0.0704(7) Uani 1 1 d . . . . .
H7 H 0.027338 0.907645 0.729974 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1150(3) 0.8090(3) 0.8544(2) 0.0590(6) Uani 1 1 d . . . . .
H8 H 0.134989 0.896854 0.909310 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2175(3) 0.6554(2) 0.99185(15) 0.0466(5) Uani 1 1 d . . . . .
H9 H 0.236077 0.740109 1.049767 0.056 Uiso 1 1 calc R U . . .
N10 N 0.1645(2) 0.40191(18) 0.81802(12) 0.0431(4) Uani 1 1 d . . . . .
C11 C 0.2547(2) 0.5173(2) 1.01464(14) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.2285(2) 0.3904(2) 0.92334(14) 0.0408(5) Uani 1 1 d . . . . .
C13 C 0.1529(3) 0.6698(2) 0.88381(15) 0.0437(5) Uani 1 1 d . . . . .
C14 C 0.1262(3) 0.5369(2) 0.79822(15) 0.0430(5) Uani 1 1 d . . . . .
C15 C 0.2699(3) 0.1751(2) 0.56942(14) 0.0442(5) Uani 1 1 d . . . . .
C16 C 0.2540(3) 0.0619(2) 0.47405(15) 0.0487(5) Uani 1 1 d . . . . .
H16 H 0.163315 -0.020738 0.466245 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3707(3) 0.0704(2) 0.39099(15) 0.0515(6) Uani 1 1 d . . . . .
C18 C 0.5073(3) 0.1899(3) 0.40174(18) 0.0603(6) Uani 1 1 d . . . . .
H18 H 0.586311 0.195260 0.345371 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5261(3) 0.3017(3) 0.4969(2) 0.0634(6) Uani 1 1 d . . . . .
H19 H 0.619397 0.382538 0.505103 0.076 Uiso 1 1 calc R U . . .
C20 C 0.4072(3) 0.2952(2) 0.58077(16) 0.0513(5) Uani 1 1 d . . . . .
H20 H 0.420440 0.371767 0.644524 0.062 Uiso 1 1 calc R U . . .
O21 O 0.1470(2) 0.16153(18) 0.64685(12) 0.0621(5) Uani 1 1 d . . . . .
H21 H 0.159(4) 0.243(3) 0.703(2) 0.093 Uiso 1 1 d . U . . .
C22 C 0.3396(4) -0.0520(3) 0.28894(19) 0.0739(8) Uani 1 1 d . . . . .
H22 H 0.251356 -0.133726 0.289864 0.089 Uiso 1 1 calc R U . . .
O23 O 0.4169(3) -0.0540(2) 0.20746(16) 0.1050(7) 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 1.344(3) . ?
C1 C11 1.420(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.410(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.412(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.351(3) . ?
C5 C14 1.422(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.347(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.421(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.381(3) . ?
C9 C13 1.387(3) . ?
C9 H9 0.9300 . ?
N10 C14 1.343(2) . ?
N10 C12 1.347(2) . ?
C11 C12 1.427(3) . ?
C13 C14 1.423(3) . ?
C15 O21 1.356(2) . ?
C15 C20 1.377(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 C22 1.486(3) . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O21 H21 0.90(3) . ?
C22 O23 1.171(3) . ?
C22 H22 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 C11 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C1 C2 C3 120.30(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C12 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C12 C4 H4 119.7 . . ?
C6 C5 C14 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C14 C5 H5 119.7 . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C13 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C13 C8 H8 119.5 . . ?
C11 C9 C13 120.93(17) . . ?
C11 C9 H9 119.5 . . ?
C13 C9 H9 119.5 . . ?
C14 N10 C12 119.07(15) . . ?
C9 C11 C1 123.77(18) . . ?
C9 C11 C12 118.07(17) . . ?
C1 C11 C12 118.15(19) . . ?
N10 C12 C4 119.26(17) . . ?
N10 C12 C11 121.80(17) . . ?
C4 C12 C11 118.93(17) . . ?
C9 C13 C8 123.73(18) . . ?
C9 C13 C14 117.41(18) . . ?
C8 C13 C14 118.85(18) . . ?
N10 C14 C5 119.21(18) . . ?
N10 C14 C13 122.68(17) . . ?
C5 C14 C13 118.11(19) . . ?
O21 C15 C20 123.42(16) . . ?
O21 C15 C16 117.64(19) . . ?
C20 C15 C16 118.93(18) . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.58(18) . . ?
C18 C17 C22 121.9(2) . . ?
C16 C17 C22 117.5(2) . . ?
C17 C18 C19 119.19(19) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.89(19) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C15 O21 H21 112.6(17) . . ?
O23 C22 C17 125.4(3) . . ?
O23 C22 H22 117.3 . . ?
C17 C22 H22 117.3 . . ?

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
C11 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C12 -0.2(3) . . . . ?
C14 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C13 0.6(3) . . . . ?
C13 C9 C11 C1 -179.31(17) . . . . ?
C13 C9 C11 C12 1.3(3) . . . . ?
C2 C1 C11 C9 -178.82(18) . . . . ?
C2 C1 C11 C12 0.6(3) . . . . ?
C14 N10 C12 C4 -178.80(16) . . . . ?
C14 N10 C12 C11 0.7(3) . . . . ?
C3 C4 C12 N10 -178.87(18) . . . . ?
C3 C4 C12 C11 1.6(3) . . . . ?
C9 C11 C12 N10 -1.9(3) . . . . ?
C1 C11 C12 N10 178.73(17) . . . . ?
C9 C11 C12 C4 177.69(17) . . . . ?
C1 C11 C12 C4 -1.7(3) . . . . ?
C11 C9 C13 C8 -178.94(17) . . . . ?
C11 C9 C13 C14 0.2(3) . . . . ?
C7 C8 C13 C9 -179.27(19) . . . . ?
C7 C8 C13 C14 1.6(3) . . . . ?
C12 N10 C14 C5 -178.51(16) . . . . ?
C12 N10 C14 C13 0.9(3) . . . . ?
C6 C5 C14 N10 -178.66(19) . . . . ?
C6 C5 C14 C13 1.9(3) . . . . ?
C9 C13 C14 N10 -1.4(3) . . . . ?
C8 C13 C14 N10 177.80(17) . . . . ?
C9 C13 C14 C5 178.03(17) . . . . ?
C8 C13 C14 C5 -2.8(3) . . . . ?
O21 C15 C16 C17 178.32(16) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C15 C16 C17 C22 -177.34(17) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C22 C17 C18 C19 178.3(2) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
O21 C15 C20 C19 -179.13(17) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C18 C17 C22 O23 -5.1(4) . . . . ?
C16 C17 C22 O23 173.3(2) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_global_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2253868'
loop_
_audit_author_name
_audit_author_address
'Artur Sikorski'
;University of Gdansk, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_journal_coeditor_?tes           
; ?
;
_iucr_compatibility_tag          ACTA95
loop_
_publ_author_foot?te
;
to whom correspondence should be addressed
;
;
to whom correspondence should be addressed
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C7 H6 O2'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5433(8)
_cell_length_b                   10.6297(10)
_cell_length_c                   12.9034(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.365(9)
_cell_angle_gamma                90
_cell_volume                     1573.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10810
_cell_measurement_theta_min      3.464
_cell_measurement_theta_max      25.000

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.999

_exptl_absorpt_process_details   
;
CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd.,
2008)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.4002
_diffrn_reflns_number            10810
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.464
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2769
_reflns_number_gt                1582
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;
_computing_data_collection       
'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_cell_refinement       
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        
'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.4925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2769
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.0899(3) 0.8335(3) 0.1582(3) 0.0709(11) Uani 1 1 d . . . . .
H1 H -0.142799 0.777393 0.123848 0.085 Uiso 1 1 calc R U . . .
C2 C -0.1108(3) 0.8816(4) 0.2501(4) 0.0804(12) Uani 1 1 d . . . . .
H2 H -0.178634 0.859390 0.278434 0.096 Uiso 1 1 calc R U . . .
C3 C -0.0313(3) 0.9654(4) 0.3045(3) 0.0801(12) Uani 1 1 d . . . . .
H3 H -0.046223 0.996623 0.369031 0.096 Uiso 1 1 calc R U . . .
C4 C 0.0672(3) 1.0011(3) 0.2634(3) 0.0679(10) Uani 1 1 d . . . . .
H4 H 0.118205 1.057701 0.299474 0.081 Uiso 1 1 calc R U . . .
C5 C 0.3195(3) 0.9846(4) -0.0040(3) 0.0812(12) Uani 1 1 d . . . . .
H5 H 0.369014 1.041351 0.033653 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3462(4) 0.9400(5) -0.0966(4) 0.0949(14) Uani 1 1 d . . . . .
H6 H 0.414211 0.966805 -0.122271 0.114 Uiso 1 1 calc R U . . .
C7 C 0.2726(5) 0.8536(4) -0.1548(4) 0.0956(14) Uani 1 1 d . . . . .
H7 H 0.293278 0.823100 -0.217760 0.115 Uiso 1 1 calc R U . . .
C8 C 0.1726(4) 0.8147(4) -0.1203(3) 0.0861(12) Uani 1 1 d . . . . .
H8 H 0.124127 0.759041 -0.160280 0.103 Uiso 1 1 calc R U . . .
C9 C 0.0388(3) 0.8214(3) 0.0175(3) 0.0655(10) Uani 1 1 d . . . . .
H9 H -0.012041 0.765353 -0.019510 0.079 Uiso 1 1 calc R U . . .
N10 N 0.1916(2) 0.9900(3) 0.1281(2) 0.0615(8) Uani 1 1 d . . . . .
C11 C 0.0128(3) 0.8675(3) 0.1120(3) 0.0589(9) Uani 1 1 d . . . . .
C12 C 0.0927(3) 0.9528(3) 0.1664(3) 0.0562(9) Uani 1 1 d . . . . .
C13 C 0.1408(3) 0.8581(3) -0.0233(3) 0.0641(10) Uani 1 1 d . . . . .
C14 C 0.2153(3) 0.9444(3) 0.0355(3) 0.0609(9) Uani 1 1 d . . . . .
C15 C 0.4223(3) 1.1055(3) 0.3011(2) 0.0540(9) Uani 1 1 d . . . . .
C16 C 0.4934(3) 1.1848(3) 0.3644(3) 0.0714(11) Uani 1 1 d . . . . .
H16 H 0.475471 1.269982 0.366722 0.086 Uiso 1 1 calc R U . . .
C17 C 0.5891(3) 1.1402(5) 0.4231(3) 0.0840(13) Uani 1 1 d . . . . .
H17 H 0.634873 1.194535 0.466864 0.101 Uiso 1 1 calc R U . . .
C18 C 0.6193(3) 1.0155(5) 0.4186(3) 0.0779(13) Uani 1 1 d . . . . .
C19 C 0.5484(3) 0.9347(4) 0.3561(3) 0.0773(12) Uani 1 1 d . . . . .
H19 H 0.567470 0.849908 0.353365 0.093 Uiso 1 1 calc R U . . .
C20 C 0.4491(3) 0.9792(3) 0.2975(3) 0.0643(10) Uani 1 1 d . . . . .
H20 H 0.400976 0.924600 0.256090 0.077 Uiso 1 1 calc R U . . .
O21 O 0.32949(19) 1.1571(2) 0.2442(2) 0.0726(8) Uani 1 1 d . . . . .
H21 H 0.290(3) 1.096(3) 0.203(3) 0.087 Uiso 1 1 d . U . . .
C22 C 0.7268(5) 0.9738(7) 0.4833(4) 0.125(2) Uani 1 1 d . . . . .
H22 H 0.761874 1.036496 0.526210 0.151 Uiso 1 1 calc R U . . .
O23 O 0.7710(4) 0.8876(5) 0.4900(3) 0.1511(18) 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 1.337(5) . ?
C1 C11 1.431(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.410(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.414(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(6) . ?
C5 C14 1.423(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.347(6) . ?
C7 H7 0.9300 . ?
C8 C13 1.420(5) . ?
C8 H8 0.9300 . ?
C9 C11 1.378(5) . ?
C9 C13 1.398(5) . ?
C9 H9 0.9300 . ?
N10 C14 1.345(4) . ?
N10 C12 1.352(4) . ?
C11 C12 1.421(4) . ?
C13 C14 1.418(5) . ?
C15 O21 1.347(3) . ?
C15 C20 1.379(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.354(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 C22 1.484(6) . ?
C19 C20 1.385(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O21 H21 0.92(4) . ?
C22 O23 1.047(6) . ?
C22 H22 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 C11 120.8(3) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C1 C2 C3 120.7(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C12 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C12 C4 H4 119.7 . . ?
C6 C5 C14 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C14 C5 H5 120.1 . . ?
C5 C6 C7 121.1(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C13 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C11 C9 C13 120.6(3) . . ?
C11 C9 H9 119.7 . . ?
C13 C9 H9 119.7 . . ?
C14 N10 C12 118.8(3) . . ?
C9 C11 C12 118.1(3) . . ?
C9 C11 C1 123.4(3) . . ?
C12 C11 C1 118.6(4) . . ?
N10 C12 C4 119.0(3) . . ?
N10 C12 C11 122.3(3) . . ?
C4 C12 C11 118.7(3) . . ?
C9 C13 C14 117.7(4) . . ?
C9 C13 C8 123.5(4) . . ?
C14 C13 C8 118.8(4) . . ?
N10 C14 C13 122.5(3) . . ?
N10 C14 C5 118.3(3) . . ?
C13 C14 C5 119.2(4) . . ?
O21 C15 C20 123.1(3) . . ?
O21 C15 C16 117.3(3) . . ?
C20 C15 C16 119.6(3) . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.1(3) . . ?
C17 C18 C22 117.7(5) . . ?
C19 C18 C22 123.1(5) . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.3(3) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C15 O21 H21 110(2) . . ?
O23 C22 C18 132.6(8) . . ?
O23 C22 H22 113.7 . . ?
C18 C22 H22 113.7 . . ?

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
C11 C1 C2 C3 -0.9(6) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C2 C3 C4 C12 -1.2(5) . . . . ?
C14 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 1.0(7) . . . . ?
C6 C7 C8 C13 -1.4(6) . . . . ?
C13 C9 C11 C12 -0.1(5) . . . . ?
C13 C9 C11 C1 -179.9(3) . . . . ?
C2 C1 C11 C9 -179.8(3) . . . . ?
C2 C1 C11 C12 0.4(5) . . . . ?
C14 N10 C12 C4 -179.6(3) . . . . ?
C14 N10 C12 C11 -0.1(4) . . . . ?
C3 C4 C12 N10 -179.8(3) . . . . ?
C3 C4 C12 C11 0.7(5) . . . . ?
C9 C11 C12 N10 0.4(4) . . . . ?
C1 C11 C12 N10 -179.8(3) . . . . ?
C9 C11 C12 C4 179.9(3) . . . . ?
C1 C11 C12 C4 -0.3(4) . . . . ?
C11 C9 C13 C14 -0.4(5) . . . . ?
C11 C9 C13 C8 -179.8(3) . . . . ?
C7 C8 C13 C9 -179.7(3) . . . . ?
C7 C8 C13 C14 0.9(5) . . . . ?
C12 N10 C14 C13 -0.4(5) . . . . ?
C12 N10 C14 C5 179.8(3) . . . . ?
C9 C13 C14 N10 0.7(5) . . . . ?
C8 C13 C14 N10 -179.9(3) . . . . ?
C9 C13 C14 C5 -179.5(3) . . . . ?
C8 C13 C14 C5 -0.2(5) . . . . ?
C6 C5 C14 N10 179.6(3) . . . . ?
C6 C5 C14 C13 -0.2(5) . . . . ?
O21 C15 C16 C17 -179.3(3) . . . . ?
C20 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 1.9(6) . . . . ?
C16 C17 C18 C19 -2.3(6) . . . . ?
C16 C17 C18 C22 178.6(4) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C22 C18 C19 C20 -180.0(4) . . . . ?
O21 C15 C20 C19 177.9(3) . . . . ?
C16 C15 C20 C19 -1.2(5) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C17 C18 C22 O23 -175.3(7) . . . . ?
C19 C18 C22 O23 5.7(9) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.038

