# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1104zf1_0m
_database_code_depnum_ccdc_archive 'CCDC 2000121'
loop_
_audit_author_name
_audit_author_address
'Fei Zhou'
;South China University of Technology
China
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_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         'C23 H16 F N O2'
_chemical_formula_sum            'C23 H16 F N O2'
_chemical_formula_weight         357.37
_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'
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'
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                   5.7119(3)
_cell_length_b                   11.2727(7)
_cell_length_c                   14.3335(8)
_cell_angle_alpha                72.075(2)
_cell_angle_beta                 83.916(2)
_cell_angle_gamma                83.801(2)
_cell_volume                     870.39(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2922
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.918
_cell_measurement_theta_min      2.754
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0890 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.9378. 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    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9745
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.754
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       ?
_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                2457
_reflns_number_total             3517
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.077
_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)+(0.0394P)²+0.3574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F2(0.8) H6(0.75) H13(0.25) F1(0.2)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C15(H15), C2(H2), C23(H23), C11(H11), C1(H1), C5(H5), C6(H6),
 C12(H12), C20(H20), C13(H13), C14(H14), C22(H22), C21(H21)
;
_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 0.3488(2) 0.27938(14) 0.66167(10) 0.0348(4) Uani 1 1 d . . . . .
O1 O 0.4631(3) 0.32643(15) 0.95202(11) 0.0416(4) Uani 1 1 d . . . . .
F2 F 1.3657(3) -0.10541(16) 0.76200(13) 0.0514(5) Uani 0.8 1 d . . P A 1
N1 N 0.6423(3) 0.23095(17) 0.94615(12) 0.0358(5) Uani 1 1 d . . . . .
C18 C 0.6513(4) 0.33068(19) 0.54051(14) 0.0285(5) Uani 1 1 d . . . . .
C8 C 0.5075(4) 0.32453(19) 0.79591(14) 0.0284(5) Uani 1 1 d . . . . .
C19 C 0.4454(4) 0.2708(2) 0.57222(14) 0.0296(5) Uani 1 1 d . . . . .
C3 C 0.2018(4) 0.4817(2) 0.85312(14) 0.0293(5) Uani 1 1 d . . . . .
C10 C 0.8485(4) 0.14152(19) 0.82804(15) 0.0315(5) Uani 1 1 d . . . . .
C7 C 0.3872(4) 0.3799(2) 0.86183(14) 0.0302(5) Uani 1 1 d . . . . .
C9 C 0.6658(4) 0.2313(2) 0.85385(15) 0.0313(5) Uani 1 1 d . . . . .
C16 C 0.4813(4) 0.3677(2) 0.68803(14) 0.0291(5) Uani 1 1 d . . . . .
H16 H 0.385349 0.450049 0.672669 0.035 Uiso 1 1 calc R . . . .
C4 C 0.0111(4) 0.4898(2) 0.79789(15) 0.0339(5) Uani 1 1 d . . . . .
H4 H 0.001892 0.428866 0.765314 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8204(4) 0.0877(2) 0.75494(16) 0.0354(5) Uani 1 1 d . . . . .
H15 H 0.681104 0.108966 0.720549 0.043 Uiso 1 1 calc R . . . .
C2 C 0.2122(4) 0.5716(2) 0.90082(15) 0.0328(5) Uani 1 1 d . . . . .
H2 H 0.341145 0.566853 0.938919 0.039 Uiso 1 1 calc R . . . .
C23 C 0.7702(4) 0.3264(2) 0.45205(15) 0.0348(5) Uani 1 1 d . . . . .
H23 H 0.912593 0.366340 0.429499 0.042 Uiso 1 1 calc R . . . .
C17 C 0.7090(4) 0.3848(2) 0.61805(15) 0.0310(5) Uani 1 1 d . . . . .
H17A H 0.738855 0.474158 0.589765 0.037 Uiso 1 1 calc R . . . .
H17B H 0.848030 0.338193 0.652179 0.037 Uiso 1 1 calc R . . . .
C11 C 1.0511(4) 0.1071(2) 0.87963(15) 0.0355(5) Uani 1 1 d . . . . .
H11 H 1.070412 0.142652 0.930188 0.043 Uiso 1 1 calc R . . . .
C1 C 0.0366(4) 0.6670(2) 0.89293(16) 0.0368(5) Uani 1 1 d . . . . .
H1 H 0.044410 0.728047 0.925495 0.044 Uiso 1 1 calc R . . . .
C5 C -0.1640(4) 0.5854(2) 0.79023(16) 0.0377(5) Uani 1 1 d . . . . .
H5 H -0.293599 0.590468 0.752375 0.045 Uiso 1 1 calc R . . . .
C6 C -0.1515(4) 0.6739(2) 0.83746(16) 0.0391(6) Uani 1 1 d . . . . .
H6 H -0.272508 0.739953 0.831930 0.047 Uiso 0.75 1 calc R . P B 1
C12 C 1.2241(4) 0.0219(2) 0.85795(17) 0.0395(6) Uani 1 1 d . . . . .
H12 H 1.361317 -0.002519 0.893580 0.047 Uiso 1 1 calc R . . . .
C20 C 0.3526(4) 0.2060(2) 0.51917(16) 0.0390(6) Uani 1 1 d . . . . .
H20 H 0.211607 0.164977 0.542409 0.047 Uiso 1 1 calc R . . . .
C13 C 1.1929(4) -0.0261(2) 0.78417(18) 0.0403(6) Uani 1 1 d . . . . .
H13 H 1.314018 -0.082683 0.767766 0.048 Uiso 0.25 1 calc R . P A 2
C14 C 0.9940(4) 0.0034(2) 0.73216(17) 0.0399(6) Uani 1 1 d . . . . .
H14 H 0.976714 -0.033269 0.682042 0.048 Uiso 1 1 calc R . . . .
C22 C 0.6786(4) 0.2629(2) 0.39662(16) 0.0408(6) Uani 1 1 d . . . . .
H22 H 0.757361 0.260683 0.335310 0.049 Uiso 1 1 calc R . . . .
C21 C 0.4735(4) 0.2031(2) 0.43042(16) 0.0440(6) Uani 1 1 d . . . . .
H21 H 0.414055 0.159229 0.392223 0.053 Uiso 1 1 calc R . . . .
F1 F -0.3065(12) 0.7593(6) 0.8285(5) 0.0546(19) Uani 0.2 1 d . . P C 2


_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 C19 1.368(2) . ?
O2 C16 1.471(2) . ?
O1 N1 1.418(2) . ?
O1 C7 1.344(2) . ?
F2 C13 1.338(3) . ?
N1 C9 1.314(3) . ?
C18 C19 1.384(3) . ?
C18 C23 1.385(3) . ?
C18 C17 1.501(3) . ?
C8 C7 1.374(3) . ?
C8 C9 1.425(3) . ?
C8 C16 1.490(3) . ?
C19 C20 1.380(3) . ?
C3 C7 1.460(3) . ?
C3 C4 1.392(3) . ?
C3 C2 1.395(3) . ?
C10 C9 1.473(3) . ?
C10 C15 1.393(3) . ?
C10 C11 1.394(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.547(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.375(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.391(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C1 H1 0.9500 . ?
C1 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(3) . ?
C6 H6 0.9500 . ?
C6 F1 1.221(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.363(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.382(3) . ?
C21 H21 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
C19 O2 C16 107.23(15) . . ?
C7 O1 N1 108.06(15) . . ?
C9 N1 O1 106.30(15) . . ?
C19 C18 C23 119.3(2) . . ?
C19 C18 C17 108.61(17) . . ?
C23 C18 C17 132.0(2) . . ?
C7 C8 C9 103.90(18) . . ?
C7 C8 C16 124.46(19) . . ?
C9 C8 C16 131.39(19) . . ?
O2 C19 C18 113.52(18) . . ?
O2 C19 C20 123.91(19) . . ?
C20 C19 C18 122.54(19) . . ?
C4 C3 C7 120.49(19) . . ?
C4 C3 C2 119.1(2) . . ?
C2 C3 C7 120.41(19) . . ?
C15 C10 C9 121.39(19) . . ?
C15 C10 C11 119.2(2) . . ?
C11 C10 C9 119.34(19) . . ?
O1 C7 C8 110.40(18) . . ?
O1 C7 C3 116.03(17) . . ?
C8 C7 C3 133.57(19) . . ?
N1 C9 C8 111.34(18) . . ?
N1 C9 C10 116.76(18) . . ?
C8 C9 C10 131.86(19) . . ?
O2 C16 C8 109.63(16) . . ?
O2 C16 H16 107.5 . . ?
O2 C16 C17 106.30(15) . . ?
C8 C16 H16 107.5 . . ?
C8 C16 C17 117.85(17) . . ?
C17 C16 H16 107.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C18 C23 H23 120.4 . . ?
C18 C23 C22 119.2(2) . . ?
C22 C23 H23 120.4 . . ?
C18 C17 C16 101.98(16) . . ?
C18 C17 H17A 111.4 . . ?
C18 C17 H17B 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(2) . . ?
C6 C1 H1 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
F1 C6 C1 120.6(4) . . ?
F1 C6 C5 119.1(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 H12 120.8 . . ?
C19 C20 H20 121.3 . . ?
C19 C20 C21 117.4(2) . . ?
C21 C20 H20 121.3 . . ?
F2 C13 C12 117.5(2) . . ?
F2 C13 C14 119.3(2) . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(2) . . ?
C14 C13 H13 118.4 . . ?
C15 C14 H14 120.9 . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 H14 120.9 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.4 . . ?

_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_1218zsi_0m
_database_code_depnum_ccdc_archive 'CCDC 2053026'
loop_
_audit_author_name
_audit_author_address
zf
;ol
China
;
_audit_update_record             
;
2020-12-29 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-12-18
_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         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_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                   5.8481(5)
_cell_length_b                   20.1032(17)
_cell_length_c                   15.8952(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.844(3)
_cell_angle_gamma                90
_cell_volume                     1841.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.792
_cell_measurement_theta_min      2.408
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0926 before and 0.0662 after correction. The Ratio of minimum to maximum transmission is 0.8899. 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    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_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  0.1022
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14808
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.026
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                1675
_reflns_number_total             3350
_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         0.164
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.057
_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)+(0.0491P)²+0.0493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1535
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C17(H17), C4(H4), C3(H3), C24(H24), C13(H13), C20(H20),
 C16(H16), C15(H15), C14(H14), C23(H23), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.2841(3) 0.54092(10) 0.73741(14) 0.0478(6) Uani 1 1 d . . . . .
O1 O 0.5437(4) 0.73084(11) 0.64061(16) 0.0663(7) Uani 1 1 d . . . . .
N1 N 0.7091(4) 0.72069(12) 0.71530(17) 0.0488(7) Uani 1 1 d . . . . .
C10 C 0.5111(5) 0.62521(14) 0.6810(2) 0.0404(8) Uani 1 1 d . . . . .
C9 C 0.4406(5) 0.55406(14) 0.6768(2) 0.0430(8) Uani 1 1 d . . . . .
H9 H 0.354052 0.545725 0.619308 0.052 Uiso 1 1 calc R . . . .
C7 C 0.6381(5) 0.50188(14) 0.6942(2) 0.0406(8) Uani 1 1 d . . . . .
H7 H 0.771468 0.521695 0.731540 0.049 Uiso 1 1 calc R . . . .
C1 C 0.3310(5) 0.47698(15) 0.7676(2) 0.0429(8) Uani 1 1 d . . . . .
C6 C 0.5284(5) 0.45049(14) 0.7442(2) 0.0414(8) Uani 1 1 d . . . . .
C18 C 0.6854(5) 0.65826(16) 0.7389(2) 0.0454(8) Uani 1 1 d . . . . .
C19 C 0.8322(6) 0.63782(16) 0.8194(2) 0.0464(9) Uani 1 1 d . . . . .
C2 C 0.1989(5) 0.44362(16) 0.8178(2) 0.0490(9) Uani 1 1 d . . . . .
H2 H 0.069249 0.463138 0.834236 0.059 Uiso 1 1 calc R . . . .
C5 C 0.5962(6) 0.38687(15) 0.7703(2) 0.0491(9) Uani 1 1 d . . . . .
H5 H 0.728403 0.367916 0.755122 0.059 Uiso 1 1 calc R . . . .
C11 C 0.4266(6) 0.67358(16) 0.6226(2) 0.0465(8) Uani 1 1 d . . . . .
C12 C 0.2399(6) 0.67370(15) 0.5483(2) 0.0453(8) Uani 1 1 d . . . . .
C17 C 0.0334(6) 0.64088(16) 0.5526(2) 0.0541(9) Uani 1 1 d . . . . .
H17 H 0.014806 0.619059 0.602583 0.065 Uiso 1 1 calc R . . . .
C4 C 0.4626(6) 0.35175(16) 0.8196(2) 0.0541(9) Uani 1 1 d . . . . .
H4 H 0.505652 0.308759 0.837236 0.065 Uiso 1 1 calc R . . . .
C3 C 0.2679(6) 0.37961(16) 0.8427(2) 0.0537(9) Uani 1 1 d . . . . .
H3 H 0.180939 0.355117 0.875566 0.064 Uiso 1 1 calc R . . . .
C24 C 0.7475(6) 0.59470(17) 0.8747(2) 0.0545(9) Uani 1 1 d . . . . .
H24 H 0.599991 0.576545 0.859403 0.065 Uiso 1 1 calc R . . . .
C13 C 0.2619(6) 0.70736(16) 0.4738(2) 0.0555(10) Uani 1 1 d . . . . .
H13 H 0.396865 0.730978 0.470575 0.067 Uiso 1 1 calc R . . . .
C8 C 0.7163(6) 0.47652(17) 0.6132(2) 0.0606(10) Uani 1 1 d . . . . .
H8A H 0.586697 0.456859 0.576349 0.091 Uiso 1 1 calc GR . . . .
H8B H 0.835931 0.443793 0.627962 0.091 Uiso 1 1 calc GR . . . .
H8C H 0.775330 0.512968 0.584272 0.091 Uiso 1 1 calc GR . . . .
C20 C 1.0527(6) 0.66423(18) 0.8435(3) 0.0634(11) Uani 1 1 d . . . . .
H20 H 1.112366 0.693154 0.807021 0.076 Uiso 1 1 calc R . . . .
C16 C -0.1434(6) 0.64036(18) 0.4837(3) 0.0649(11) Uani 1 1 d . . . . .
H16 H -0.281388 0.618340 0.487120 0.078 Uiso 1 1 calc R . . . .
C15 C -0.1168(7) 0.67252(19) 0.4092(3) 0.0660(11) Uani 1 1 d . . . . .
H15 H -0.235650 0.671495 0.362141 0.079 Uiso 1 1 calc R . . . .
C14 C 0.0847(7) 0.70589(18) 0.4046(3) 0.0656(11) Uani 1 1 d . . . . .
H14 H 0.101917 0.727695 0.354445 0.079 Uiso 1 1 calc R . . . .
C23 C 0.8803(7) 0.57846(19) 0.9524(2) 0.0689(11) Uani 1 1 d . . . . .
H23 H 0.822016 0.549692 0.989362 0.083 Uiso 1 1 calc R . . . .
C21 C 1.1839(6) 0.6478(2) 0.9212(3) 0.0718(12) Uani 1 1 d . . . . .
H21 H 1.331083 0.666029 0.937089 0.086 Uiso 1 1 calc R . . . .
C22 C 1.0989(8) 0.6049(2) 0.9749(3) 0.0764(12) Uani 1 1 d . . . . .
H22 H 1.189193 0.593548 1.026916 0.092 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 C9 1.462(3) . ?
O2 C1 1.383(3) . ?
O1 N1 1.412(3) . ?
O1 C11 1.345(4) . ?
N1 C18 1.324(4) . ?
C10 C9 1.487(4) . ?
C10 C18 1.416(4) . ?
C10 C11 1.377(4) . ?
C9 H9 0.9800 . ?
C9 C7 1.550(4) . ?
C7 H7 0.9800 . ?
C7 C6 1.512(4) . ?
C7 C8 1.526(4) . ?
C1 C6 1.378(4) . ?
C1 C2 1.377(4) . ?
C6 C5 1.381(4) . ?
C18 C19 1.473(4) . ?
C19 C24 1.385(4) . ?
C19 C20 1.387(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.390(4) . ?
C11 C12 1.464(4) . ?
C12 C17 1.388(4) . ?
C12 C13 1.390(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.372(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.381(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.378(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.381(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.368(5) . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.374(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.366(5) . ?
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
C1 O2 C9 106.7(2) . . ?
C11 O1 N1 107.8(2) . . ?
C18 N1 O1 106.6(2) . . ?
C18 C10 C9 130.1(3) . . ?
C11 C10 C9 125.7(3) . . ?
C11 C10 C18 104.0(3) . . ?
O2 C9 C10 110.1(2) . . ?
O2 C9 H9 107.6 . . ?
O2 C9 C7 106.9(2) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C7 116.8(2) . . ?
C7 C9 H9 107.6 . . ?
C9 C7 H7 108.9 . . ?
C6 C7 C9 100.7(2) . . ?
C6 C7 H7 108.9 . . ?
C6 C7 C8 115.5(3) . . ?
C8 C7 C9 113.4(3) . . ?
C8 C7 H7 108.9 . . ?
C6 C1 O2 113.0(3) . . ?
C2 C1 O2 123.8(3) . . ?
C2 C1 C6 123.1(3) . . ?
C1 C6 C7 109.1(3) . . ?
C1 C6 C5 119.2(3) . . ?
C5 C6 C7 131.6(3) . . ?
N1 C18 C10 111.1(3) . . ?
N1 C18 C19 115.9(3) . . ?
C10 C18 C19 133.0(3) . . ?
C24 C19 C18 120.5(3) . . ?
C24 C19 C20 118.8(3) . . ?
C20 C19 C18 120.6(3) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 116.9(3) . . ?
C3 C2 H2 121.5 . . ?
C6 C5 H5 120.7 . . ?
C6 C5 C4 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
O1 C11 C10 110.5(3) . . ?
O1 C11 C12 116.9(3) . . ?
C10 C11 C12 132.6(3) . . ?
C17 C12 C11 119.7(3) . . ?
C17 C12 C13 118.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.1(4) . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.1 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
