# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 2128901'
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.473(2)
_cell_length_b                   6.0831(6)
_cell_length_c                   19.451(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.583(6)
_cell_angle_gamma                90
_cell_volume                     2148.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0664 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8193. 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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9320
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.515
_diffrn_reflns_theta_min         2.130
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1208
_reflns_number_total             2200
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.033
_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)+(0.0781P)²+0.6741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1769
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C15(H15), C11(H11), C1(H1), C3(H3), C14(H14), C12(H12),
 C13(H13), C5(H5), C4(H4)
;
_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 0.64212(12) 0.0727(3) 0.59001(10) 0.0578(6) Uani 1 1 d . . . . .
N1 N 0.62882(13) 0.2353(3) 0.54578(11) 0.0407(6) Uani 1 1 d . . . . .
C7 C 0.59760(14) 0.5859(4) 0.45155(12) 0.0330(6) Uani 1 1 d . . . . .
C9 C 0.67380(14) 0.4239(4) 0.55474(12) 0.0341(6) Uani 1 1 d . . . . .
C2 C 0.55260(15) 0.3963(4) 0.44504(12) 0.0373(7) Uani 1 1 d . . . . .
C10 C 0.73490(14) 0.4302(4) 0.61590(12) 0.0348(6) Uani 1 1 d . . . . .
C8 C 0.65742(14) 0.5920(4) 0.50870(12) 0.0341(6) Uani 1 1 d . . . . .
H8 H 0.687466 0.719819 0.515076 0.041 Uiso 1 1 calc R . . . .
C6 C 0.58073(15) 0.7557(4) 0.40225(12) 0.0399(7) Uani 1 1 d . . . . .
H6 H 0.611415 0.881980 0.405083 0.048 Uiso 1 1 calc R . . . .
C15 C 0.74257(14) 0.6156(4) 0.65883(12) 0.0378(7) Uani 1 1 d . . . . .
H15 H 0.709272 0.735135 0.648356 0.045 Uiso 1 1 calc R . . . .
C11 C 0.78557(15) 0.2613(4) 0.63057(13) 0.0405(7) Uani 1 1 d . . . . .
H11 H 0.781438 0.135507 0.601175 0.049 Uiso 1 1 calc R . . . .
C1 C 0.57130(15) 0.2272(4) 0.49307(14) 0.0424(7) Uani 1 1 d . . . . .
H1 H 0.541524 0.098814 0.488126 0.051 Uiso 1 1 calc R . . . .
C3 C 0.49008(15) 0.3830(5) 0.39079(14) 0.0470(8) Uani 1 1 d . . . . .
H3 H 0.459219 0.256883 0.386396 0.056 Uiso 1 1 calc R . . . .
C14 C 0.79879(15) 0.6254(5) 0.71679(13) 0.0435(7) Uani 1 1 d . . . . .
H14 H 0.803137 0.750536 0.746506 0.052 Uiso 1 1 calc R . . . .
C12 C 0.84834(16) 0.4554(5) 0.73160(14) 0.0466(8) Uani 1 1 d . . . . .
H12 H 0.886445 0.462321 0.771638 0.056 Uiso 1 1 calc R . . . .
C13 C 0.84237(15) 0.2749(5) 0.68796(13) 0.0456(7) Uani 1 1 d . . . . .
H13 H 0.877349 0.159194 0.697287 0.055 Uiso 1 1 calc R . . . .
C5 C 0.52029(16) 0.7395(5) 0.35028(13) 0.0487(8) Uani 1 1 d . . . . .
H5 H 0.509029 0.855588 0.317387 0.058 Uiso 1 1 calc R . . . .
C4 C 0.47474(16) 0.5544(5) 0.34477(14) 0.0514(8) Uani 1 1 d . . . . .
H4 H 0.432564 0.547379 0.308605 0.062 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.304(3) . ?
N1 C9 1.408(3) . ?
N1 C1 1.335(3) . ?
C7 C2 1.413(3) . ?
C7 C8 1.417(3) . ?
C7 C6 1.405(3) . ?
C9 C10 1.482(3) . ?
C9 C8 1.356(3) . ?
C2 C1 1.390(3) . ?
C2 C3 1.416(3) . ?
C10 C15 1.395(3) . ?
C10 C11 1.384(3) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.365(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C13 1.387(3) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.370(4) . ?
C14 H14 0.9500 . ?
C14 C12 1.376(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.398(4) . ?
C4 H4 0.9500 . ?

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
O1 N1 C9 120.0(2) . . ?
O1 N1 C1 120.4(2) . . ?
C1 N1 C9 119.6(2) . . ?
C2 C7 C8 116.9(2) . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 124.0(2) . . ?
N1 C9 C10 117.7(2) . . ?
C8 C9 N1 118.5(2) . . ?
C8 C9 C10 123.7(2) . . ?
C7 C2 C3 120.0(2) . . ?
C1 C2 C7 118.3(2) . . ?
C1 C2 C3 121.8(3) . . ?
C15 C10 C9 118.7(2) . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 C15 119.1(2) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.0(2) . . ?
C9 C8 H8 118.5 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0(2) . . ?
C14 C15 H15 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C13 120.3(3) . . ?
C13 C11 H11 119.8 . . ?
N1 C1 C2 123.6(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C15 C14 H14 119.7 . . ?
C12 C14 C15 120.5(3) . . ?
C12 C14 H14 119.7 . . ?
C14 C12 H12 120.2 . . ?
C14 C12 C13 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C13 H13 119.8 . . ?
C12 C13 C11 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?

_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_04_sq
_database_code_depnum_ccdc_archive 'CCDC 2142641'
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2022-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 N2 O2'
_chemical_formula_sum            'C22 H28 N2 O2'
_chemical_formula_weight         352.46
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   22.8147(12)
_cell_length_b                   22.8147(12)
_cell_length_c                   10.5217(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4742.9(6)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.947
_cell_measurement_theta_min      2.193
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0903 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.9109. 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    1.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1710
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13322
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.193
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1361
_reflns_number_total             2167
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+8.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1559
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.04209(8) 0.39146(8) 0.64475(14) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.08608(9) 0.38057(9) 0.58415(16) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.19129(11) 0.38278(11) 0.5862(2) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.231397 0.391277 0.629272 0.036 Uiso 1 1 calc R . . . .
C6 C 0.14612(11) 0.39473(11) 0.6481(2) 0.0284(5) Uani 1 1 d . . . . .
C8 C 0.18081(11) 0.35791(11) 0.45891(19) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.21393(11) 0.32231(11) 0.26898(19) 0.0269(5) Uani 1 1 d . . . . .
C11 C 0.07327(11) 0.35642(11) 0.4660(2) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.031993 0.347069 0.426689 0.034 Uiso 1 1 calc R . . . .
C9 C 0.22732(11) 0.34657(11) 0.3937(2) 0.0287(5) Uani 1 1 d . . . . .
H9 H 0.268181 0.355330 0.433947 0.034 Uiso 1 1 calc R . . . .
C5 C 0.15321(11) 0.42109(12) 0.7807(2) 0.0326(6) Uani 1 1 d . . . . .
H5A H 0.115133 0.386971 0.832340 0.039 Uiso 1 1 calc R . . . .
H5B H 0.149520 0.462513 0.778635 0.039 Uiso 1 1 calc R . . . .
C4 C 0.21942(12) 0.43764(12) 0.8455(2) 0.0350(6) Uani 1 1 d . . . . .
H4A H 0.257765 0.471575 0.794146 0.042 Uiso 1 1 calc R . . . .
H4B H 0.223031 0.396202 0.849511 0.042 Uiso 1 1 calc R . . . .
C3 C 0.22451(13) 0.46507(14) 0.9794(2) 0.0444(7) Uani 1 1 d . . . . .
H3A H 0.185748 0.431347 1.030291 0.053 Uiso 1 1 calc R . . . .
H3B H 0.221367 0.506764 0.975155 0.053 Uiso 1 1 calc R . . . .
C2 C 0.29061(15) 0.48116(18) 1.0467(3) 0.0611(9) Uani 1 1 d . . . . .
H2A H 0.286681 0.488906 1.138066 0.073 Uiso 1 1 calc R . . . .
H2B H 0.297091 0.441494 1.039548 0.073 Uiso 1 1 calc R . . . .
C1 C 0.35192(17) 0.54235(18) 0.9928(3) 0.0784(11) Uani 1 1 d . . . . .
H1A H 0.356838 0.534632 0.902805 0.118 Uiso 1 1 calc GR . . . .
H1B H 0.392384 0.550097 1.039382 0.118 Uiso 1 1 calc GR . . . .
H1C H 0.346375 0.582083 1.001286 0.118 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.313(2) . ?
N1 C6 1.411(3) . ?
N1 C11 1.332(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.357(3) . ?
C7 C8 1.428(3) . ?
C6 C5 1.495(3) . ?
C8 C10 1.428(3) 16 ?
C8 C9 1.392(3) . ?
C10 C11 1.411(3) 16 ?
C10 C9 1.397(3) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.535(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.508(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
O1 N1 C6 118.12(17) . . ?
O1 N1 C11 120.08(18) . . ?
C11 N1 C6 121.81(18) . . ?
C6 C7 H7 118.8 . . ?
C6 C7 C8 122.5(2) . . ?
C8 C7 H7 118.8 . . ?
N1 C6 C5 115.75(18) . . ?
C7 C6 N1 118.24(19) . . ?
C7 C6 C5 126.0(2) . . ?
C7 C8 C10 117.42(19) . 16 ?
C9 C8 C7 123.0(2) . . ?
C9 C8 C10 119.57(18) . 16 ?
C11 C10 C8 118.35(19) 16 16 ?
C9 C10 C8 120.38(19) . 16 ?
C9 C10 C11 121.27(19) . 16 ?
N1 C11 C10 121.7(2) . 16 ?
N1 C11 H11 119.1 . . ?
C10 C11 H11 119.1 16 . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C6 C5 C4 114.35(18) . . ?
H5A C5 H5B 107.6 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C5 C4 C3 112.28(19) . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C4 C3 C2 112.9(2) . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 C3 113.2(3) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
-1 2 0 1.785
-4 4 1 4.558
-5 6 1 6.067

_platon_squeeze_details          
;
TITL 04_a.res in R-3
CELL   22.8147   22.8147   10.5217     90.00     90.00    120.00
SPGR R-3
# Solvent Accessible Volume =       727
# Electrons Found in S.A.V. =       120
# Note: Atoms in Void are Labelled as Cxxx and Qxxx for all Others
C101 0.030 0.086 0.024 !       4.62 eA-3
C102 1.000 0.998 0.063 !       2.32 eA-3
Q103 0.015 0.695 0.247 !       0.88 eA-3
Q104 0.766 0.609 0.375 !       0.83 eA-3
Q105 0.860 0.450 0.468 !       0.81 eA-3
Q106 0.719 0.935 0.846 !       0.79 eA-3
Q107 0.086 0.724 0.436 !       0.76 eA-3
Q108 0.718 0.227 0.025 !       0.67 eA-3
Q109 0.564 0.068 0.523 !       0.65 eA-3
Q110 0.845 0.532 0.218 !       0.64 eA-3
Q111 0.236 0.085 0.373 !       0.58 eA-3
Q112 0.234 0.195 0.371 !       0.57 eA-3
Q113 0.384 0.859 0.179 !       0.50 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.016 242 41 ' '
2 0.333 0.667 -0.195 243 41 ' '
3 0.667 0.333 0.162 244 41 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'
