# 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_124z108612_0m
_database_code_depnum_ccdc_archive 'CCDC 2241702'
loop_
_audit_author_name
_audit_author_address
amine
;SCUT(South China University of Technology)
China
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-12-04
_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         'C16 H12 Br F3 N2'
_chemical_formula_sum            'C16 H12 Br F3 N2'
_chemical_formula_weight         369.19
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.1120(5)
_cell_length_b                   7.3561(3)
_cell_length_c                   18.2597(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.730(2)
_cell_angle_gamma                90
_cell_volume                     1603.48(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4749
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.057
_shelx_estimated_absorpt_T_max   0.881
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    2.591
_exptl_absorpt_correction_T_max  0.7454
_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 0.1076 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.6888. 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    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.19
_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  0.0502
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11895
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         2.594
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_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                2594
_reflns_number_total             3232
_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         0.294
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.037
_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)+(0.0272P)²+0.6806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C15(H15), C11(H11), C13(H13), C12(H12), C14(H14)
;
_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
Br1 Br 0.89066(2) -0.33518(3) 0.58271(2) 0.03323(10) Uani 1 1 d . . . . .
F3 F 0.77800(18) 0.0429(2) 0.61704(10) 0.0615(5) Uani 1 1 d . . . . .
F2 F 0.65371(16) -0.1354(3) 0.55902(11) 0.0609(5) Uani 1 1 d . . . . .
N1 N 0.83231(16) 0.1621(2) 0.31230(11) 0.0216(4) Uani 1 1 d . . . . .
F1 F 0.6517(2) 0.1468(3) 0.53112(12) 0.0804(8) Uani 1 1 d . . . . .
C6 C 0.84806(19) 0.0532(3) 0.37700(12) 0.0197(5) Uani 1 1 d . . . . .
C3 C 0.8715(2) -0.1711(3) 0.50119(13) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.9476(2) 0.1087(3) 0.21405(13) 0.0373(6) Uani 1 1 d . . . . .
C1 C 0.9274(2) -0.0844(3) 0.38579(13) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.973856 -0.102380 0.349375 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7936(2) -0.0314(3) 0.49328(13) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.7080(2) 0.6360(3) 0.32152(14) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.7823(2) 0.0813(3) 0.43141(13) 0.0238(5) Uani 1 1 d . . . . .
H5 H 0.729516 0.177914 0.426283 0.029 Uiso 1 1 calc R . . . .
C2 C 0.9387(2) -0.1954(3) 0.44779(13) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.993302 -0.289344 0.453761 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7496(2) 0.3109(3) 0.29890(13) 0.0227(5) Uani 1 1 d . . . . .
H8A H 0.679487 0.272127 0.315439 0.027 Uiso 1 1 calc R . . . .
H8B H 0.732072 0.336074 0.244915 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7922(2) 0.4848(3) 0.33982(14) 0.0258(5) Uani 1 1 d . . . . .
H9A H 0.805594 0.462353 0.394062 0.031 Uiso 1 1 calc R . . . .
H9B H 0.864173 0.521079 0.325263 0.031 Uiso 1 1 calc R . . . .
C7 C 0.8956(2) 0.1327(3) 0.26006(14) 0.0253(5) Uani 1 1 d . . . . .
C15 C 0.6299(2) 0.6730(3) 0.36695(16) 0.0337(6) Uani 1 1 d . . . . .
H15 H 0.630022 0.603637 0.410832 0.040 Uiso 1 1 calc R . . . .
C11 C 0.7048(2) 0.7378(3) 0.25730(15) 0.0319(6) Uani 1 1 d . . . . .
H11 H 0.757367 0.713941 0.225321 0.038 Uiso 1 1 calc R . . . .
C13 C 0.5499(3) 0.9098(4) 0.2849(2) 0.0498(9) Uani 1 1 d . . . . .
H13 H 0.495840 1.003173 0.272354 0.060 Uiso 1 1 calc R . . . .
C12 C 0.6257(3) 0.8742(3) 0.23919(18) 0.0437(8) Uani 1 1 d . . . . .
H12 H 0.624228 0.942867 0.194981 0.052 Uiso 1 1 calc R . . . .
C14 C 0.5516(2) 0.8108(4) 0.3489(2) 0.0482(8) Uani 1 1 d . . . . .
H14 H 0.499227 0.836541 0.380765 0.058 Uiso 1 1 calc R . . . .
C16 C 0.7197(3) 0.0046(4) 0.54989(16) 0.0444(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
Br1 C3 1.900(2) . ?
F3 C16 1.338(4) . ?
F2 C16 1.331(3) . ?
N1 C6 1.413(3) . ?
N1 C8 1.476(3) . ?
N1 C7 1.338(3) . ?
F1 C16 1.340(3) . ?
C6 C1 1.386(3) . ?
C6 C5 1.390(3) . ?
C3 C4 1.386(3) . ?
C3 C2 1.384(3) . ?
N2 C7 1.146(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C4 C5 1.389(3) . ?
C4 C16 1.501(4) . ?
C10 C9 1.508(3) . ?
C10 C15 1.386(4) . ?
C10 C11 1.387(4) . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C14 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.366(5) . ?
C13 C14 1.374(5) . ?
C12 H12 0.9500 . ?
C14 H14 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
C6 N1 C8 123.42(19) . . ?
C7 N1 C6 119.44(19) . . ?
C7 N1 C8 117.14(19) . . ?
C1 C6 N1 120.2(2) . . ?
C1 C6 C5 119.7(2) . . ?
C5 C6 N1 120.0(2) . . ?
C4 C3 Br1 122.96(18) . . ?
C2 C3 Br1 117.48(17) . . ?
C2 C3 C4 119.6(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 C16 122.2(2) . . ?
C5 C4 C16 117.8(2) . . ?
C15 C10 C9 121.1(2) . . ?
C15 C10 C11 118.4(2) . . ?
C11 C10 C9 120.5(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.09(19) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C10 C9 C8 110.44(19) . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N2 C7 N1 178.4(3) . . ?
C10 C15 H15 119.7 . . ?
C10 C15 C14 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
F3 C16 F1 106.0(3) . . ?
F3 C16 C4 112.6(3) . . ?
F2 C16 F3 106.5(2) . . ?
F2 C16 F1 106.3(3) . . ?
F2 C16 C4 113.0(2) . . ?
F1 C16 C4 111.9(2) . . ?

_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_124z1085112_0m
_database_code_depnum_ccdc_archive 'CCDC 2241703'
loop_
_audit_author_name
_audit_author_address
cyanamide
;SCUT(South China University of Technology)
China
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-12-04
_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         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_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                   6.5729(5)
_cell_length_b                   29.957(2)
_cell_length_c                   6.9575(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.913(3)
_cell_angle_gamma                90
_cell_volume                     1345.19(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2523
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.032
_cell_measurement_theta_min      2.720
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1326 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.7231. 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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_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  0.0670
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10375
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         2.720
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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                1819
_reflns_number_total             2743
_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         0.200
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.071
_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)+(0.0478P)²+0.2512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1288
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C6(H6), C2(H2), C5(H5), C3(H3), 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
O2 O 0.6341(2) 0.61773(4) 0.3798(2) 0.0375(4) Uani 1 1 d . . . . .
O1 O 0.89980(19) 0.56582(4) 0.4447(2) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.4467(2) 0.44103(5) 0.1960(2) 0.0279(4) Uani 1 1 d . . . . .
N2 N 0.0909(3) 0.41708(6) 0.0442(3) 0.0425(5) Uani 1 1 d . . . . .
C10 C 0.4872(3) 0.48720(6) 0.2384(2) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.3268(3) 0.51799(6) 0.1988(3) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.190909 0.508171 0.143306 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6134(3) 0.40729(6) 0.2402(3) 0.0280(4) Uani 1 1 d . . . . .
H8A H 0.671591 0.407821 0.382291 0.034 Uiso 1 1 calc R . . . .
H8B H 0.725932 0.415149 0.169801 0.034 Uiso 1 1 calc R . . . .
C9 C 0.2559(3) 0.42822(6) 0.1146(3) 0.0304(5) Uani 1 1 d . . . . .
C12 C 0.3631(3) 0.56328(6) 0.2398(3) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.254208 0.584568 0.213534 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6899(3) 0.50033(6) 0.3193(3) 0.0281(4) Uani 1 1 d . . . . .
H15 H 0.800752 0.479519 0.345969 0.034 Uiso 1 1 calc R . . . .
C14 C 0.7188(3) 0.54496(6) 0.3576(2) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.5605(3) 0.57572(6) 0.3189(3) 0.0277(4) Uani 1 1 d . . . . .
C7 C 0.5365(3) 0.36027(6) 0.1816(3) 0.0359(5) Uani 1 1 d . . . . .
H7A H 0.422011 0.352244 0.249254 0.043 Uiso 1 1 calc R . . . .
H7B H 0.483527 0.358997 0.038664 0.043 Uiso 1 1 calc R . . . .
C1 C 0.7137(3) 0.32777(6) 0.2372(3) 0.0372(5) Uani 1 1 d . . . . .
C16 C 0.8552(3) 0.61266(6) 0.4282(3) 0.0378(5) Uani 1 1 d . . . . .
H16A H 0.920352 0.626044 0.324626 0.045 Uiso 1 1 calc R . . . .
H16B H 0.910539 0.627872 0.553465 0.045 Uiso 1 1 calc R . . . .
C6 C 0.8532(3) 0.32150(7) 0.1132(4) 0.0462(6) Uani 1 1 d . . . . .
H6 H 0.831339 0.336400 -0.009564 0.055 Uiso 1 1 calc R . . . .
C2 C 0.7461(4) 0.30564(8) 0.4148(4) 0.0525(6) Uani 1 1 d . . . . .
H2 H 0.651661 0.309413 0.501320 0.063 Uiso 1 1 calc R . . . .
C5 C 1.0233(4) 0.29404(8) 0.1646(5) 0.0652(8) Uani 1 1 d . . . . .
H5 H 1.117768 0.290180 0.078132 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9176(4) 0.27782(8) 0.4667(5) 0.0722(9) Uani 1 1 d . . . . .
H3 H 0.939560 0.262599 0.588689 0.087 Uiso 1 1 calc R . . . .
C4 C 1.0554(4) 0.27227(8) 0.3420(6) 0.0783(10) Uani 1 1 d . . . . .
H4 H 1.172512 0.253408 0.378484 0.094 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
O2 C13 1.385(2) . ?
O2 C16 1.436(2) . ?
O1 C14 1.378(2) . ?
O1 C16 1.434(2) . ?
N1 C10 1.429(2) . ?
N1 C8 1.480(2) . ?
N1 C9 1.331(2) . ?
N2 C9 1.152(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.402(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.526(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.362(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.369(3) . ?
C14 C13 1.378(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C1 1.511(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.383(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.380(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(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
C13 O2 C16 104.76(14) . . ?
C14 O1 C16 105.19(14) . . ?
C10 N1 C8 121.12(14) . . ?
C9 N1 C10 119.37(15) . . ?
C9 N1 C8 119.50(15) . . ?
C11 C10 N1 119.84(16) . . ?
C11 C10 C15 121.45(17) . . ?
C15 C10 N1 118.71(16) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.70(17) . . ?
C12 C11 H11 119.6 . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 C7 112.35(15) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
N2 C9 N1 179.9(3) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.45(17) . . ?
C13 C12 H12 121.3 . . ?
C10 C15 H15 122.0 . . ?
C14 C15 C10 116.01(17) . . ?
C14 C15 H15 122.0 . . ?
C15 C14 O1 127.19(17) . . ?
C15 C14 C13 122.90(17) . . ?
C13 C14 O1 109.86(16) . . ?
C12 C13 O2 128.53(17) . . ?
C12 C13 C14 121.50(17) . . ?
C14 C13 O2 109.92(16) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C1 C7 C8 109.03(15) . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C6 C1 C7 119.76(19) . . ?
C2 C1 C7 121.3(2) . . ?
C2 C1 C6 118.9(2) . . ?
O2 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
O1 C16 O2 107.76(14) . . ?
O1 C16 H16A 110.2 . . ?
O1 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
