# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2233986'
loop_
_audit_author_name
_audit_author_address
'Zhicheng Jiang'
;TIanjin University
China
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2023-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_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/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                   7.4851(15)
_cell_length_b                   16.193(3)
_cell_length_c                   11.059(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.87(3)
_cell_angle_gamma                90
_cell_volume                     1340.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12848
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2141
_reflns_number_total             3039
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.019
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1595
_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 Aromatic/amide H refined with riding coordinates:
 C15(H15), C7(H7), C16(H16), C12(H12), C4(H4), C3(H3), C1(H1), C6(H6), C8(H8),
 C13(H13)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
O2 O 0.36431(18) 0.17270(7) 0.79440(11) 0.0629(4) Uani 1 1 d . . . . .
C9 C 0.2535(2) 0.50511(9) 0.92355(14) 0.0426(4) Uani 1 1 d . . . . .
C14 C 0.3293(2) 0.25144(9) 0.83002(15) 0.0455(4) Uani 1 1 d . . . . .
C15 C 0.3856(2) 0.31342(10) 0.75312(15) 0.0494(4) Uani 1 1 d . . . . .
H15 H 0.441177 0.299658 0.681215 0.059 Uiso 1 1 calc R U . . .
O1 O 0.1996(2) 0.94820(8) 1.03065(13) 0.0768(5) Uani 1 1 d . . . . .
C2 C 0.1703(2) 0.82390(9) 0.91893(14) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.0982(2) 0.78796(10) 0.81562(14) 0.0478(4) Uani 1 1 d . . . . .
H7 H 0.031907 0.819834 0.761292 0.057 Uiso 1 1 calc R U . . .
C16 C 0.3603(2) 0.39465(10) 0.78195(14) 0.0461(4) Uani 1 1 d . . . . .
H16 H 0.397595 0.435448 0.728799 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2793(2) 0.41737(9) 0.89008(14) 0.0412(4) Uani 1 1 d . . . . .
C12 C 0.2241(2) 0.35457(9) 0.96583(14) 0.0459(4) Uani 1 1 d . . . . .
H12 H 0.169935 0.368189 1.038284 0.055 Uiso 1 1 calc R U . . .
C5 C 0.22220(19) 0.65604(9) 0.87339(13) 0.0416(4) Uani 1 1 d . . . . .
C4 C 0.2969(2) 0.69321(10) 0.97589(14) 0.0451(4) Uani 1 1 d . . . . .
H4 H 0.365067 0.661773 1.029728 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2269(2) 0.51963(9) 1.05052(16) 0.0487(4) Uani 1 1 d . . . . .
C3 C 0.2711(2) 0.77567(10) 0.99837(14) 0.0443(4) Uani 1 1 d . . . . .
H3 H 0.321476 0.799487 1.067389 0.053 Uiso 1 1 calc R U . . .
C1 C 0.1410(3) 0.91185(11) 0.94312(17) 0.0569(5) Uani 1 1 d . . . . .
H1 H 0.072716 0.941711 0.887411 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1242(2) 0.70552(10) 0.79293(14) 0.0476(4) Uani 1 1 d . . . . .
H6 H 0.075784 0.682228 0.722891 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2439(2) 0.56837(10) 0.84530(15) 0.0472(4) Uani 1 1 d . . . . .
H8 H 0.252048 0.554906 0.763819 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2470(2) 0.27249(9) 0.93703(15) 0.0467(4) Uani 1 1 d . . . . .
H13 H 0.207479 0.231508 0.989113 0.056 Uiso 1 1 calc R U . . .
N1 N 0.2026(2) 0.52801(10) 1.15129(14) 0.0726(5) Uani 1 1 d . . . . .
C17 C 0.3199(3) 0.10756(11) 0.87391(19) 0.0705(6) Uani 1 1 d . . . . .
H17A H 0.359454 0.056034 0.840725 0.106 Uiso 1 1 calc R U . . .
H17B H 0.192801 0.106018 0.883930 0.106 Uiso 1 1 calc R U . . .
H17C H 0.377446 0.116458 0.950993 0.106 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.3611(18) . ?
O2 C17 1.416(2) . ?
C9 C11 1.482(2) . ?
C9 C10 1.441(2) . ?
C9 C8 1.342(2) . ?
C14 C15 1.385(2) . ?
C14 C13 1.385(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(2) . ?
O1 C1 1.210(2) . ?
C2 C7 1.384(2) . ?
C2 C3 1.390(2) . ?
C2 C1 1.466(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.373(2) . ?
C16 H16 0.9300 . ?
C16 C11 1.398(2) . ?
C11 C12 1.384(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C5 C4 1.393(2) . ?
C5 C6 1.397(2) . ?
C5 C8 1.463(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(2) . ?
C10 N1 1.140(2) . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C14 O2 C17 118.04(14) . . ?
C10 C9 C11 114.87(13) . . ?
C8 C9 C11 125.21(15) . . ?
C8 C9 C10 119.81(14) . . ?
O2 C14 C15 116.06(14) . . ?
O2 C14 C13 124.61(14) . . ?
C13 C14 C15 119.31(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.61(15) . . ?
C16 C15 H15 119.7 . . ?
C7 C2 C3 119.11(14) . . ?
C7 C2 C1 120.11(15) . . ?
C3 C2 C1 120.78(15) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.36(14) . . ?
C6 C7 H7 119.8 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C11 121.07(14) . . ?
C11 C16 H16 119.5 . . ?
C16 C11 C9 121.72(13) . . ?
C12 C11 C9 120.79(14) . . ?
C12 C11 C16 117.49(14) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 121.95(15) . . ?
C13 C12 H12 119.0 . . ?
C4 C5 C6 118.09(14) . . ?
C4 C5 C8 123.20(14) . . ?
C6 C5 C8 118.70(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.79(14) . . ?
C3 C4 H4 119.6 . . ?
N1 C10 C9 177.19(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(14) . . ?
C4 C3 H3 119.7 . . ?
O1 C1 C2 124.42(17) . . ?
O1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C7 C6 C5 121.04(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C9 C8 C5 127.50(15) . . ?
C9 C8 H8 116.3 . . ?
C5 C8 H8 116.3 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.57(14) . . ?
C12 C13 H13 120.2 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C14 C15 C16 -178.57(15) . . . . ?
O2 C14 C13 C12 177.67(15) . . . . ?
C9 C11 C12 C13 -179.78(15) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C15 C14 C13 C12 -0.6(2) . . . . ?
C15 C16 C11 C9 179.01(15) . . . . ?
C15 C16 C11 C12 -0.7(2) . . . . ?
C2 C7 C6 C5 0.5(2) . . . . ?
C7 C2 C3 C4 -1.0(2) . . . . ?
C7 C2 C1 O1 -179.63(17) . . . . ?
C16 C11 C12 C13 -0.1(2) . . . . ?
C11 C9 C8 C5 -178.70(14) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C5 C4 C3 C2 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C4 C5 C8 C9 34.8(2) . . . . ?
C10 C9 C11 C16 -159.67(16) . . . . ?
C10 C9 C11 C12 20.0(2) . . . . ?
C10 C9 C8 C5 5.3(3) . . . . ?
C3 C2 C7 C6 0.9(2) . . . . ?
C3 C2 C1 O1 -0.1(3) . . . . ?
C1 C2 C7 C6 -179.55(15) . . . . ?
C1 C2 C3 C4 179.45(15) . . . . ?
C6 C5 C4 C3 1.5(2) . . . . ?
C6 C5 C8 C9 -146.21(17) . . . . ?
C8 C9 C11 C16 24.1(2) . . . . ?
C8 C9 C11 C12 -156.16(17) . . . . ?
C8 C5 C4 C3 -179.47(14) . . . . ?
C8 C5 C6 C7 179.32(14) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C17 O2 C14 C15 175.87(16) . . . . ?
C17 O2 C14 C13 -2.5(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_r20220811b
_database_code_depnum_ccdc_archive 'CCDC 2233988'
loop_
_audit_author_name
_audit_author_address
'Zhicheng Jiang'
;Tianjin University
China
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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/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                   4.7360(5)
_cell_length_b                   9.8182(10)
_cell_length_c                   28.395(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.950(9)
_cell_angle_gamma                90
_cell_volume                     1320.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2496
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.5410
_cell_measurement_theta_min      2.1830
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.195
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    3.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    3.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    3.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237402000
_diffrn_orient_matrix_UB_12      -0.0588521000
_diffrn_orient_matrix_UB_13      0.0140238000
_diffrn_orient_matrix_UB_21      0.0016482000
_diffrn_orient_matrix_UB_22      -0.0407329000
_diffrn_orient_matrix_UB_23      -0.0206248000
_diffrn_orient_matrix_UB_31      0.1478159000
_diffrn_orient_matrix_UB_32      0.0098981000
_diffrn_orient_matrix_UB_33      -0.0015805000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1739
_reflns_number_total             2692
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.044
_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)+(0.0594P)²+0.7618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1732
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 -0.2889(4) 0.8941(2) 0.40348(6) 0.0391(6) Uani 1 1 d . . . . .
O2 O 1.5913(4) 0.0394(2) 0.26149(7) 0.0436(6) Uani 1 1 d . . . . .
N1 N 0.5163(6) 0.3046(3) 0.46020(8) 0.0524(8) Uani 1 1 d . . . . .
C1 C -0.3881(7) 0.9314(3) 0.44830(10) 0.0439(8) Uani 1 1 d . . . . .
H1A H -0.509890 1.011720 0.445254 0.066 Uiso 1 1 calc R U . . .
H1B H -0.227155 0.952601 0.469173 0.066 Uiso 1 1 calc R U . . .
H1C H -0.495933 0.855808 0.461562 0.066 Uiso 1 1 calc R U . . .
C2 C -0.1100(6) 0.7840(3) 0.40214(9) 0.0285(6) Uani 1 1 d . . . . .
C3 C -0.0358(6) 0.7027(3) 0.43990(9) 0.0324(7) Uani 1 1 d . . . . .
H3 H -0.113914 0.719019 0.469977 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1526(6) 0.5974(3) 0.43372(9) 0.0319(7) Uani 1 1 d . . . . .
H4 H 0.202064 0.541757 0.459945 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2727(5) 0.5701(3) 0.39042(8) 0.0254(6) Uani 1 1 d . . . . .
C6 C 0.1884(6) 0.6529(3) 0.35239(9) 0.0292(6) Uani 1 1 d . . . . .
H6 H 0.261707 0.635835 0.322008 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0035(6) 0.7570(3) 0.35841(9) 0.0311(6) Uani 1 1 d . . . . .
H7 H -0.048844 0.812235 0.332222 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4759(6) 0.4572(3) 0.38587(9) 0.0285(6) Uani 1 1 d . . . . .
C9 C 0.5046(6) 0.3699(3) 0.42683(9) 0.0361(7) Uani 1 1 d . . . . .
C10 C 0.6278(6) 0.4333(3) 0.34761(9) 0.0308(7) Uani 1 1 d . . . . .
H10 H 0.594223 0.495418 0.322490 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8377(5) 0.3277(3) 0.33752(9) 0.0257(6) Uani 1 1 d . . . . .
C12 C 0.9171(6) 0.2201(3) 0.36690(9) 0.0310(7) Uani 1 1 d . . . . .
H12 H 0.829569 0.209656 0.396550 0.037 Uiso 1 1 calc R U . . .
C13 C 1.1207(6) 0.1289(3) 0.35342(9) 0.0311(7) Uani 1 1 d . . . . .
H13 H 1.173988 0.056963 0.374078 0.037 Uiso 1 1 calc R U . . .
C14 C 1.2486(5) 0.1405(3) 0.31032(9) 0.0275(6) Uani 1 1 d . . . . .
C15 C 1.1712(6) 0.2467(3) 0.28063(8) 0.0308(6) Uani 1 1 d . . . . .
H15 H 1.258431 0.256033 0.250923 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9691(6) 0.3381(3) 0.29399(9) 0.0305(6) Uani 1 1 d . . . . .
H16 H 0.917369 0.410050 0.273223 0.037 Uiso 1 1 calc R U . . .
C17 C 1.4686(6) 0.0413(3) 0.29805(10) 0.0347(7) Uani 1 1 d . . . . .
H17 H 1.516899 -0.026108 0.320792 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.412(3) . ?
O1 C2 1.374(3) . ?
O2 C17 1.198(3) . ?
N1 C9 1.145(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.378(4) . ?
C2 C7 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.404(4) . ?
C5 C8 1.475(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.359(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.449(4) . ?
C8 C10 1.334(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.468(4) . ?
C11 C12 1.394(4) . ?
C11 C16 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 C15 1.386(4) . ?
C14 C17 1.472(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(4) . ?
C16 H16 0.9500 . ?
C17 H17 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
C2 O1 C1 116.3(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.7(2) . . ?
O1 C2 C7 115.1(2) . . ?
C3 C2 C7 119.2(2) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.2(2) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 117.0(2) . . ?
C4 C5 C8 120.0(2) . . ?
C6 C5 C8 123.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C5 115.3(2) . . ?
C10 C8 C5 124.4(2) . . ?
C10 C8 C9 120.3(3) . . ?
N1 C9 C8 176.5(3) . . ?
C8 C10 H10 114.4 . . ?
C8 C10 C11 131.3(3) . . ?
C11 C10 H10 114.4 . . ?
C12 C11 C10 126.5(2) . . ?
C12 C11 C16 117.7(2) . . ?
C16 C11 C10 115.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 C17 118.6(2) . . ?
C15 C14 C17 122.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
O2 C17 C14 124.8(3) . . ?
O2 C17 H17 117.6 . . ?
C14 C17 H17 117.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -178.2(3) . . . . ?
O1 C2 C7 C6 178.5(2) . . . . ?
C1 O1 C2 C3 4.6(4) . . . . ?
C1 O1 C2 C7 -174.6(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C2 C7 C6 -0.7(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C3 C4 C5 C8 179.3(3) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
C4 C5 C8 C9 8.4(4) . . . . ?
C4 C5 C8 C10 -171.4(3) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
C5 C8 C10 C11 179.5(3) . . . . ?
C6 C5 C8 C9 -170.8(3) . . . . ?
C6 C5 C8 C10 9.4(4) . . . . ?
C7 C2 C3 C4 0.9(4) . . . . ?
C8 C5 C6 C7 -179.1(2) . . . . ?
C8 C10 C11 C12 3.4(5) . . . . ?
C8 C10 C11 C16 -176.4(3) . . . . ?
C9 C8 C10 C11 -0.3(5) . . . . ?
C10 C11 C12 C13 -179.0(3) . . . . ?
C10 C11 C16 C15 179.3(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C12 C13 C14 C17 179.0(3) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C13 C14 C17 O2 178.7(3) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C15 C14 C17 O2 -3.0(4) . . . . ?
C16 C11 C12 C13 0.8(4) . . . . ?
C17 C14 C15 C16 -178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.968
_oxdiff_exptl_absorpt_empirical_full_min 0.570
####################################################################### 
# 
# 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_r20220920a
_database_code_depnum_ccdc_archive 'CCDC 2233987'
loop_
_audit_author_name
_audit_author_address
'Zhicheng Jiang'
;Tianjin University
China
;
_audit_update_record             
;
2023-01-03 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8204(3)
_cell_length_b                   10.5317(8)
_cell_length_c                   32.715(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1316.31(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.0510
_cell_measurement_theta_min      2.0320
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10748
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50   10.00    --  -30.00  45.00   0.00  360
  2  ω   -120.00  45.00   0.50   10.00    --  -30.00  45.00  90.00  330
  3  ω   -120.00  45.00   0.50   10.00    --  -30.00  45.00 180.00  330
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0032556000
_diffrn_orient_matrix_UB_12      0.0030088000
_diffrn_orient_matrix_UB_13      0.0216507000
_diffrn_orient_matrix_UB_21      -0.0148580000
_diffrn_orient_matrix_UB_22      0.0670850000
_diffrn_orient_matrix_UB_23      -0.0009572000
_diffrn_orient_matrix_UB_31      -0.1850338000
_diffrn_orient_matrix_UB_32      -0.0053177000
_diffrn_orient_matrix_UB_33      0.0004847000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2138
_reflns_number_total             2687
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.055
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1122
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.4654(6) 0.5897(2) 0.53714(6) 0.0422(6) Uani 1 1 d . . . . .
O2 O 0.0381(8) 0.2709(2) 0.16136(7) 0.0586(8) Uani 1 1 d . . . . .
N1 N 0.5030(9) 0.1634(3) 0.36685(8) 0.0485(8) Uani 1 1 d . . . . .
C1 C 0.6320(10) 0.5203(3) 0.56890(9) 0.0487(10) Uani 1 1 d . . . . .
H1A H 0.867960 0.495913 0.560149 0.073 Uiso 1 1 calc R U . . .
H1B H 0.495565 0.443806 0.574994 0.073 Uiso 1 1 calc R U . . .
H1C H 0.647434 0.573293 0.593453 0.073 Uiso 1 1 calc R U . . .
C2 C 0.4514(9) 0.5355(3) 0.49927(9) 0.0324(7) Uani 1 1 d . . . . .
C3 C 0.5640(8) 0.4153(3) 0.49012(8) 0.0331(7) Uani 1 1 d . . . . .
H3 H 0.659036 0.362313 0.510827 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5376(8) 0.3723(3) 0.45036(9) 0.0333(8) Uani 1 1 d . . . . .
H4 H 0.616475 0.289096 0.443996 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3994(8) 0.4471(3) 0.41948(9) 0.0302(7) Uani 1 1 d . . . . .
C6 C 0.2787(8) 0.5677(3) 0.42998(9) 0.0333(8) Uani 1 1 d . . . . .
H6 H 0.176525 0.620205 0.409607 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3053(9) 0.6113(3) 0.46921(9) 0.0356(8) Uani 1 1 d . . . . .
H7 H 0.223204 0.693862 0.475862 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3798(8) 0.4025(3) 0.37708(9) 0.0317(7) Uani 1 1 d . . . . .
C9 C 0.4418(9) 0.2689(3) 0.37076(9) 0.0346(8) Uani 1 1 d . . . . .
C10 C 0.3306(8) 0.4771(3) 0.34445(9) 0.0321(8) Uani 1 1 d . . . . .
H10 H 0.316481 0.565520 0.350023 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2958(8) 0.4418(3) 0.30160(9) 0.0296(7) Uani 1 1 d . . . . .
C12 C 0.1357(8) 0.3303(3) 0.28844(9) 0.0308(7) Uani 1 1 d . . . . .
H12 H 0.049112 0.271284 0.307932 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1026(8) 0.3053(3) 0.24767(9) 0.0304(7) Uani 1 1 d . . . . .
H13 H -0.008614 0.229163 0.239088 0.037 Uiso 1 1 calc R U . . .
C14 C 0.2286(8) 0.3893(3) 0.21868(9) 0.0308(7) Uani 1 1 d . . . . .
C15 C 0.3895(8) 0.5007(3) 0.23123(9) 0.0322(7) Uani 1 1 d . . . . .
H15 H 0.479385 0.558743 0.211639 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4176(8) 0.5263(3) 0.27236(9) 0.0299(7) Uani 1 1 d . . . . .
H16 H 0.522793 0.603613 0.280911 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1863(10) 0.3629(3) 0.17478(10) 0.0418(9) Uani 1 1 d . . . . .
H17 H 0.281681 0.421934 0.155874 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.421(4) . ?
O1 C2 1.365(3) . ?
O2 C17 1.204(4) . ?
N1 C9 1.143(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.369(4) . ?
C2 C7 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 C6 1.394(4) . ?
C5 C8 1.467(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.367(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.441(4) . ?
C8 C10 1.339(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.457(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.365(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C14 C15 1.387(4) . ?
C14 C17 1.472(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C17 H17 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
C2 O1 C1 117.8(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.9(3) . . ?
O1 C2 C7 114.8(3) . . ?
C3 C2 C7 120.3(3) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 C8 121.8(3) . . ?
C6 C5 C8 120.5(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C5 116.1(2) . . ?
C10 C8 C5 124.9(3) . . ?
C10 C8 C9 118.8(3) . . ?
N1 C9 C8 177.0(4) . . ?
C8 C10 H10 115.5 . . ?
C8 C10 C11 129.0(3) . . ?
C11 C10 H10 115.5 . . ?
C12 C11 C10 123.6(3) . . ?
C16 C11 C10 117.9(3) . . ?
C16 C11 C12 118.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 C17 120.7(3) . . ?
C15 C14 C17 119.8(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
O2 C17 C14 124.0(3) . . ?
O2 C17 H17 118.0 . . ?
C14 C17 H17 118.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.4(3) . . . . ?
O1 C2 C7 C6 179.6(3) . . . . ?
C1 O1 C2 C3 4.8(4) . . . . ?
C1 O1 C2 C7 -176.2(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C3 C4 C5 C8 178.4(3) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C4 C5 C8 C9 12.6(5) . . . . ?
C4 C5 C8 C10 -163.1(3) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C5 C8 C10 C11 -177.7(3) . . . . ?
C6 C5 C8 C9 -167.5(3) . . . . ?
C6 C5 C8 C10 16.7(5) . . . . ?
C7 C2 C3 C4 1.6(4) . . . . ?
C8 C5 C6 C7 -178.1(3) . . . . ?
C8 C10 C11 C12 34.1(5) . . . . ?
C8 C10 C11 C16 -148.4(3) . . . . ?
C9 C8 C10 C11 6.6(5) . . . . ?
C10 C11 C12 C13 177.9(3) . . . . ?
C10 C11 C16 C15 -179.0(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C11 C16 C15 -1.4(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C12 C13 C14 C17 -178.9(3) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C13 C14 C17 O2 1.5(5) . . . . ?
C14 C15 C16 C11 1.5(5) . . . . ?
C15 C14 C17 O2 -177.1(3) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C17 C14 C15 C16 177.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.394
_oxdiff_exptl_absorpt_empirical_full_min 0.463
