# 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_5-mpq
_database_code_depnum_ccdc_archive 'CCDC 2255886'
loop_
_audit_author_name
_audit_author_address
'longjie Wang'
;Yun nan university
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   7.6245(11)
_cell_length_b                   7.2463(10)
_cell_length_c                   21.937(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.996(8)
_cell_angle_gamma                90
_cell_volume                     1209.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.53
_cell_measurement_theta_min      3.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.409
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8463
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.920
_diffrn_reflns_theta_min         3.514
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1627
_reflns_number_total             2196
_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 1.5 (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         0.207
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.119
_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)+(0.0718P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1300
_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:
 C1(H1), C4(H4), C10(H10), C2(H2), C9(H9), C5(H5), C11(H11), C3(H3), C13(H13),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.90613(15) 0.75183(14) 0.81944(4) 0.0489(3) Uani 1 1 d . . . . .
C1 C 0.71197(17) 0.63051(19) 0.66601(5) 0.0351(4) Uani 1 1 d . . . . .
H1 H 0.732080 0.551834 0.632566 0.042 Uiso 1 1 calc R U . . .
N1 N 0.3836(2) 0.72558(18) 0.43886(6) 0.0520(4) Uani 1 1 d . . . . .
C4 C 0.83013(18) 0.6279(2) 0.71720(5) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.930021 0.549268 0.718527 0.043 Uiso 1 1 calc R U . . .
C6 C 0.47875(19) 0.74694(18) 0.54762(6) 0.0362(4) Uani 1 1 d . . . . .
C8 C 0.5652(2) 0.74491(19) 0.66232(6) 0.0361(4) Uani 1 1 d . . . . .
C10 C 0.64926(19) 0.7957(2) 0.53083(6) 0.0396(4) Uani 1 1 d . . . . .
H10 H 0.740442 0.821535 0.561386 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3487(2) 0.71881(19) 0.49910(7) 0.0425(4) Uani 1 1 d . . . . .
C14 C 0.4318(2) 0.73645(19) 0.60939(7) 0.0380(4) Uani 1 1 d . . . . .
C16 C 0.8004(2) 0.7417(2) 0.76643(6) 0.0376(4) Uani 1 1 d . . . . .
C2 C 0.6540(2) 0.8555(2) 0.76367(6) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.632954 0.932769 0.797370 0.050 Uiso 1 1 calc R U . . .
C9 C 0.53881(19) 0.8574(2) 0.71251(6) 0.0432(4) Uani 1 1 d . . . . .
H9 H 0.439472 0.936776 0.711329 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1728(2) 0.6861(2) 0.51280(8) 0.0552(5) Uani 1 1 d . . . . .
H5 H 0.085012 0.664481 0.480709 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6809(2) 0.8052(2) 0.47078(6) 0.0478(4) Uani 1 1 d . . . . .
H11 H 0.794174 0.837944 0.458869 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5451(3) 0.7664(2) 0.42682(7) 0.0530(5) Uani 1 1 d . . . . .
H3 H 0.571449 0.769827 0.385142 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2579(2) 0.7112(2) 0.61954(7) 0.0494(4) Uani 1 1 d . . . . .
H13 H 0.223473 0.711110 0.660344 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1296(2) 0.6855(2) 0.57141(8) 0.0584(5) Uani 1 1 d . . . . .
H7 H 0.010558 0.667410 0.580157 0.070 Uiso 1 1 calc R U . . .
C15 C 1.0596(2) 0.6391(3) 0.82392(7) 0.0608(5) Uani 1 1 d . . . . .
H15A H 1.132976 0.668215 0.790253 0.091 Uiso 1 1 calc R U . . .
H15B H 1.025264 0.508794 0.821616 0.091 Uiso 1 1 calc R U . . .
H15C H 1.126223 0.662623 0.862980 0.091 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 C16 1.3701(17) . ?
O1 C15 1.425(2) . ?
C1 H1 0.9500 . ?
C1 C4 1.3900(17) . ?
C1 C8 1.3904(19) . ?
N1 C12 1.367(2) . ?
N1 C3 1.311(2) . ?
C4 H4 0.9500 . ?
C4 C16 1.3901(19) . ?
C6 C10 1.420(2) . ?
C6 C12 1.418(2) . ?
C6 C14 1.427(2) . ?
C8 C14 1.490(2) . ?
C8 C9 1.3958(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3573(19) . ?
C12 C5 1.415(2) . ?
C14 C13 1.373(2) . ?
C16 C2 1.385(2) . ?
C2 H2 0.9500 . ?
C2 C9 1.3761(19) . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C5 C7 1.349(2) . ?
C11 H11 0.9500 . ?
C11 C3 1.393(2) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C13 C7 1.400(2) . ?
C7 H7 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C15 117.38(12) . . ?
C4 C1 H1 119.0 . . ?
C4 C1 C8 121.93(12) . . ?
C8 C1 H1 119.0 . . ?
C3 N1 C12 116.86(14) . . ?
C1 C4 H4 120.4 . . ?
C1 C4 C16 119.20(13) . . ?
C16 C4 H4 120.4 . . ?
C10 C6 C14 123.62(14) . . ?
C12 C6 C10 116.48(13) . . ?
C12 C6 C14 119.78(14) . . ?
C1 C8 C14 121.57(12) . . ?
C1 C8 C9 117.51(13) . . ?
C9 C8 C14 120.70(13) . . ?
C6 C10 H10 120.3 . . ?
C11 C10 C6 119.46(14) . . ?
C11 C10 H10 120.3 . . ?
N1 C12 C6 123.19(16) . . ?
N1 C12 C5 117.56(15) . . ?
C5 C12 C6 119.23(15) . . ?
C6 C14 C8 122.34(14) . . ?
C13 C14 C6 118.03(14) . . ?
C13 C14 C8 119.59(14) . . ?
O1 C16 C4 124.94(14) . . ?
O1 C16 C2 115.47(13) . . ?
C2 C16 C4 119.59(13) . . ?
C16 C2 H2 119.7 . . ?
C9 C2 C16 120.53(13) . . ?
C9 C2 H2 119.7 . . ?
C8 C9 H9 119.4 . . ?
C2 C9 C8 121.24(14) . . ?
C2 C9 H9 119.4 . . ?
C12 C5 H5 120.0 . . ?
C7 C5 C12 120.05(16) . . ?
C7 C5 H5 120.0 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C3 119.21(16) . . ?
C3 C11 H11 120.4 . . ?
N1 C3 C11 124.67(15) . . ?
N1 C3 H3 117.7 . . ?
C11 C3 H3 117.7 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C7 121.82(16) . . ?
C7 C13 H13 119.1 . . ?
C5 C7 C13 120.94(17) . . ?
C5 C7 H7 119.5 . . ?
C13 C7 H7 119.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C16 C2 C9 179.73(13) . . . . ?
C1 C4 C16 O1 179.82(13) . . . . ?
C1 C4 C16 C2 0.0(2) . . . . ?
C1 C8 C14 C6 -51.64(19) . . . . ?
C1 C8 C14 C13 126.00(17) . . . . ?
C1 C8 C9 C2 0.2(2) . . . . ?
N1 C12 C5 C7 -177.30(14) . . . . ?
C4 C1 C8 C14 -175.19(13) . . . . ?
C4 C1 C8 C9 -0.6(2) . . . . ?
C4 C16 C2 C9 -0.4(2) . . . . ?
C6 C10 C11 C3 -0.1(2) . . . . ?
C6 C12 C5 C7 1.3(2) . . . . ?
C6 C14 C13 C7 3.6(2) . . . . ?
C8 C1 C4 C16 0.5(2) . . . . ?
C8 C14 C13 C7 -174.10(14) . . . . ?
C10 C6 C12 N1 4.1(2) . . . . ?
C10 C6 C12 C5 -174.43(13) . . . . ?
C10 C6 C14 C8 -10.6(2) . . . . ?
C10 C6 C14 C13 171.76(14) . . . . ?
C10 C11 C3 N1 2.1(3) . . . . ?
C12 N1 C3 C11 -0.9(2) . . . . ?
C12 C6 C10 C11 -2.7(2) . . . . ?
C12 C6 C14 C8 173.41(12) . . . . ?
C12 C6 C14 C13 -4.3(2) . . . . ?
C12 C5 C7 C13 -2.0(3) . . . . ?
C14 C6 C10 C11 -178.86(14) . . . . ?
C14 C6 C12 N1 -179.61(13) . . . . ?
C14 C6 C12 C5 1.9(2) . . . . ?
C14 C8 C9 C2 174.80(13) . . . . ?
C14 C13 C7 C5 -0.5(3) . . . . ?
C16 C2 C9 C8 0.3(2) . . . . ?
C9 C8 C14 C6 133.94(15) . . . . ?
C9 C8 C14 C13 -48.42(19) . . . . ?
C3 N1 C12 C6 -2.3(2) . . . . ?
C3 N1 C12 C5 176.22(15) . . . . ?
C15 O1 C16 C4 1.0(2) . . . . ?
C15 O1 C16 C2 -179.13(13) . . . . ?

_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_5-mqb
_database_code_depnum_ccdc_archive 'CCDC 2255887'
loop_
_audit_author_name
_audit_author_address
'longjie Wang'
;Yun nan university
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_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 ?
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1492(12)
_cell_length_b                   4.0685(4)
_cell_length_c                   14.1566(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.372(10)
_cell_angle_gamma                90
_cell_volume                     639.33(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    301.15
_cell_measurement_reflns_used    1984
_cell_measurement_theta_min      1.8100
_cell_measurement_theta_max      28.0810
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.791
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            2558
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.977
_diffrn_reflns_theta_min         1.835
_diffrn_ambient_temperature      301.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.791
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.704
_reflns_number_gt                1691
_reflns_number_total             2558
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2558
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0965
_refine_ls_restrained_S_all      1.144
_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)+(0.0631P)²+1.2667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2505
_refine_ls_wR_factor_ref         0.2698
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.631(8)
 0.369(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15)
3.b Fitted hexagon refined as free rotating group:
 C9(C4,C5,C6,C7,C8), C10(C11,C12,C13,C14,C15)
3.c 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
O1 O 0.0919(7) 0.583(3) 0.3049(5) 0.075(3) Uani 1 1 d . . . . .
O2 O 0.2749(6) 0.806(2) 0.3019(5) 0.059(2) Uani 1 1 d . . . . .
N1 N 0.2235(8) 0.446(2) 0.9821(6) 0.054(2) Uani 1 1 d . . . . .
C1 C 0.1254(10) 0.627(3) 0.9632(7) 0.057(3) Uani 1 1 d . . . . .
H1 H 0.082485 0.689751 1.013495 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0827(10) 0.731(3) 0.8717(7) 0.054(3) Uani 1 1 d . . . . .
H2 H 0.013511 0.858896 0.862406 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1434(8) 0.643(2) 0.7969(7) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.115739 0.708970 0.735857 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3213(5) 0.3609(14) 0.7408(3) 0.041(2) Uani 1 1 d G . . . .
C4 C 0.2502(4) 0.4472(15) 0.8125(4) 0.042(2) Uani 1 1 d G . . . .
C5 C 0.2855(5) 0.361(2) 0.9059(3) 0.045(2) Uani 1 1 d G . . . .
C6 C 0.3920(6) 0.188(2) 0.9277(3) 0.051(3) Uani 1 1 d G . . . .
H6 H 0.415715 0.129513 0.990200 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4632(5) 0.1011(18) 0.8560(4) 0.057(3) Uani 1 1 d G . . . .
H7 H 0.534432 -0.014627 0.870596 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4278(5) 0.1878(16) 0.7626(4) 0.048(2) Uani 1 1 d G . . . .
H8 H 0.475392 0.130043 0.714634 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2868(5) 0.4319(15) 0.6362(3) 0.042(2) Uani 1 1 d G . . . .
C11 C 0.3703(4) 0.5833(16) 0.5835(4) 0.045(2) Uani 1 1 d G . . . .
H11 H 0.446113 0.638571 0.612199 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3406(4) 0.6521(19) 0.4880(4) 0.048(2) Uani 1 1 d G . . . .
H12 H 0.396465 0.753358 0.452804 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2273(5) 0.569(2) 0.4452(3) 0.044(2) Uani 1 1 d G . . . .
C14 C 0.1438(4) 0.418(2) 0.4978(4) 0.047(2) Uani 1 1 d G . . . .
H14 H 0.068019 0.362812 0.469185 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1735(5) 0.3493(16) 0.5933(4) 0.049(2) Uani 1 1 d G . . . .
H15 H 0.117664 0.248021 0.628580 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1893(9) 0.648(3) 0.3448(7) 0.051(2) Uani 1 1 d . . . . .
C17 C 0.2439(11) 0.901(4) 0.2043(7) 0.074(4) Uani 1 1 d . . . . .
H17A H 0.228320 0.707799 0.166126 0.111 Uiso 1 1 calc R U . . .
H17B H 0.309459 1.021435 0.181630 0.111 Uiso 1 1 calc R U . . .
H17C H 0.173135 1.036757 0.200172 0.111 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 C16 1.206(12) . ?
O2 C16 1.343(12) . ?
O2 C17 1.445(11) . ?
N1 C1 1.326(13) . ?
N1 C5 1.380(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.402(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.432(10) . ?
C9 C4 1.3900 . ?
C9 C8 1.3900 . ?
C9 C10 1.522(6) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C13 C16 1.480(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 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
C16 O2 C17 116.3(9) . . ?
C1 N1 C5 116.5(8) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(10) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(10) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(9) . . ?
C4 C3 H3 120.2 . . ?
C4 C9 C8 120.0 . . ?
C4 C9 C10 123.5(4) . . ?
C8 C9 C10 116.4(4) . . ?
C9 C4 C3 123.5(5) . . ?
C5 C4 C3 116.4(5) . . ?
C5 C4 C9 120.0 . . ?
N1 C5 C4 124.2(6) . . ?
N1 C5 C6 115.7(6) . . ?
C4 C5 C6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 C15 120.0 . . ?
C15 C10 C9 121.0(4) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 C16 122.3(6) . . ?
C14 C13 C16 117.7(5) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
O1 C16 O2 122.7(9) . . ?
O1 C16 C13 124.6(9) . . ?
O2 C16 C13 112.7(8) . . ?
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
N1 C1 C2 C3 0.2(16) . . . . ?
N1 C5 C6 C7 -177.7(7) . . . . ?
C1 N1 C5 C4 -1.4(11) . . . . ?
C1 N1 C5 C6 176.2(7) . . . . ?
C1 C2 C3 C4 -0.3(14) . . . . ?
C2 C3 C4 C9 -176.4(7) . . . . ?
C2 C3 C4 C5 -0.3(11) . . . . ?
C3 C4 C5 N1 1.3(8) . . . . ?
C3 C4 C5 C6 -176.2(7) . . . . ?
C9 C4 C5 N1 177.5(7) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C10 C11 C12 -179.7(6) . . . . ?
C9 C10 C15 C14 179.7(6) . . . . ?
C4 C9 C8 C7 0.0 . . . . ?
C4 C9 C10 C11 130.0(4) . . . . ?
C4 C9 C10 C15 -49.7(7) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 N1 C1 C2 0.6(14) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C8 C9 C4 C3 175.9(7) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C8 C9 C10 C11 -52.8(6) . . . . ?
C8 C9 C10 C15 127.5(4) . . . . ?
C10 C9 C4 C3 -6.9(8) . . . . ?
C10 C9 C4 C5 177.1(6) . . . . ?
C10 C9 C8 C7 -177.3(6) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 C16 177.7(8) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C13 C16 O1 -179.6(9) . . . . ?
C12 C13 C16 O2 -0.4(11) . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C14 C13 C16 O1 -1.9(13) . . . . ?
C14 C13 C16 O2 177.3(6) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C16 C13 C14 C15 -177.8(7) . . . . ?
C17 O2 C16 O1 1.0(15) . . . . ?
C17 O2 C16 C13 -178.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.631(8)
2 0.369(8)

####################################################################### 
# 
# 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_5-qba
_database_code_depnum_ccdc_archive 'CCDC 2255888'
loop_
_audit_author_name
_audit_author_address
'longjie Wang'
;Yun nan university
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_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                   10.278(2)
_cell_length_b                   7.3347(16)
_cell_length_c                   15.573(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.695(11)
_cell_angle_gamma                90
_cell_volume                     1163.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3504
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_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  0.0781
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10699
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         1.999
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2141
_reflns_number_total             2878
_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 1.5 (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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.138(17)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.060
_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)+(0.1196P)²+0.0124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C12(H12), C9(H9), C5(H5), C11(H11), C3(H3), C13(H13), C7(H7),
 C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.33503(11) 0.19549(18) 0.44763(10) 0.0375(4) Uani 1 1 d . . . . .
H1 H 0.268497 0.195764 0.412108 0.056 Uiso 1 1 calc R U . . .
O2 O 0.23906(11) 0.43813(19) 0.49885(9) 0.0376(4) Uani 1 1 d . . . . .
N1 N 1.13282(13) 0.33183(19) 0.82156(11) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.65857(14) 0.3669(2) 0.70362(12) 0.0250(4) Uani 1 1 d . . . . .
C4 C 0.65566(15) 0.2340(2) 0.63957(12) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.725338 0.152745 0.640756 0.033 Uiso 1 1 calc R U . . .
C6 C 0.55208(15) 0.4865(2) 0.70140(12) 0.0293(4) Uani 1 1 d . . . . .
H6 H 0.551795 0.575451 0.743919 0.035 Uiso 1 1 calc R U . . .
C8 C 0.44515(15) 0.3403(2) 0.57197(12) 0.0264(4) Uani 1 1 d . . . . .
C10 C 1.00289(15) 0.3445(2) 0.83236(12) 0.0261(4) Uani 1 1 d . . . . .
C12 C 0.55049(15) 0.2208(2) 0.57397(12) 0.0274(4) Uani 1 1 d . . . . .
H12 H 0.550491 0.132014 0.531334 0.033 Uiso 1 1 calc R U . . .
C14 C 0.76854(15) 0.3729(2) 0.77582(12) 0.0251(4) Uani 1 1 d . . . . .
C16 C 0.90297(15) 0.3624(2) 0.75983(12) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.32975(15) 0.3310(2) 0.50263(12) 0.0275(4) Uani 1 1 d . . . . .
C9 C 0.44688(15) 0.4725(2) 0.63583(13) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.376642 0.552805 0.634676 0.036 Uiso 1 1 calc R U . . .
C5 C 0.97000(17) 0.3414(2) 0.91716(13) 0.0331(4) Uani 1 1 d . . . . .
H5 H 1.035202 0.325224 0.964035 0.040 Uiso 1 1 calc R U . . .
C11 C 0.94344(16) 0.3777(2) 0.67706(12) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.881373 0.394645 0.628503 0.033 Uiso 1 1 calc R U . . .
C3 C 1.16448(16) 0.3409(2) 0.74261(14) 0.0325(5) Uani 1 1 d . . . . .
H3 H 1.252595 0.328706 0.735819 0.039 Uiso 1 1 calc R U . . .
C13 C 0.74171(16) 0.3789(2) 0.86017(13) 0.0308(4) Uani 1 1 d . . . . .
H13 H 0.655440 0.394340 0.870702 0.037 Uiso 1 1 calc R U . . .
C7 C 1.07401(17) 0.3677(2) 0.66812(14) 0.0322(4) Uani 1 1 d . . . . .
H7 H 1.101876 0.378441 0.613931 0.039 Uiso 1 1 calc R U . . .
C15 C 0.84191(18) 0.3621(3) 0.93063(14) 0.0366(5) Uani 1 1 d . . . . .
H15 H 0.820982 0.365029 0.986889 0.044 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 H1 0.8200 . ?
O1 C2 1.318(2) . ?
O2 C2 1.2143(19) . ?
N1 C10 1.371(2) . ?
N1 C3 1.315(3) . ?
C1 C4 1.392(2) . ?
C1 C6 1.399(2) . ?
C1 C14 1.484(2) . ?
C4 H4 0.9300 . ?
C4 C12 1.388(2) . ?
C6 H6 0.9300 . ?
C6 C9 1.388(2) . ?
C8 C12 1.390(2) . ?
C8 C2 1.495(2) . ?
C8 C9 1.388(3) . ?
C10 C16 1.427(2) . ?
C10 C5 1.407(3) . ?
C12 H12 0.9300 . ?
C14 C16 1.438(2) . ?
C14 C13 1.378(3) . ?
C16 C11 1.411(3) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C15 1.369(3) . ?
C11 H11 0.9300 . ?
C11 C7 1.370(2) . ?
C3 H3 0.9300 . ?
C3 C7 1.400(3) . ?
C13 H13 0.9300 . ?
C13 C15 1.406(3) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C3 N1 C10 118.57(15) . . ?
C4 C1 C6 118.65(15) . . ?
C4 C1 C14 120.31(14) . . ?
C6 C1 C14 120.91(15) . . ?
C1 C4 H4 119.5 . . ?
C12 C4 C1 121.08(15) . . ?
C12 C4 H4 119.5 . . ?
C1 C6 H6 119.9 . . ?
C9 C6 C1 120.10(16) . . ?
C9 C6 H6 119.9 . . ?
C12 C8 C2 121.87(16) . . ?
C9 C8 C12 119.31(16) . . ?
C9 C8 C2 118.82(14) . . ?
N1 C10 C16 121.24(17) . . ?
N1 C10 C5 118.32(16) . . ?
C5 C10 C16 120.44(16) . . ?
C4 C12 C8 120.01(16) . . ?
C4 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
C16 C14 C1 121.26(16) . . ?
C13 C14 C1 119.57(15) . . ?
C13 C14 C16 119.08(16) . . ?
C10 C16 C14 118.29(17) . . ?
C11 C16 C10 117.48(15) . . ?
C11 C16 C14 124.15(15) . . ?
O1 C2 C8 113.94(13) . . ?
O2 C2 O1 123.68(16) . . ?
O2 C2 C8 122.37(16) . . ?
C6 C9 H9 119.6 . . ?
C8 C9 C6 120.85(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C5 H5 120.0 . . ?
C15 C5 C10 119.93(17) . . ?
C15 C5 H5 120.0 . . ?
C16 C11 H11 120.0 . . ?
C7 C11 C16 120.09(17) . . ?
C7 C11 H11 120.0 . . ?
N1 C3 H3 117.9 . . ?
N1 C3 C7 124.18(16) . . ?
C7 C3 H3 117.9 . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C15 121.45(16) . . ?
C15 C13 H13 119.3 . . ?
C11 C7 C3 118.32(18) . . ?
C11 C7 H7 120.8 . . ?
C3 C7 H7 120.8 . . ?
C5 C15 C13 120.60(19) . . ?
C5 C15 H15 119.7 . . ?
C13 C15 H15 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C10 C16 C14 179.28(14) . . . . ?
N1 C10 C16 C11 -3.8(2) . . . . ?
N1 C10 C5 C15 177.04(16) . . . . ?
N1 C3 C7 C11 -2.8(3) . . . . ?
C1 C4 C12 C8 -0.7(3) . . . . ?
C1 C6 C9 C8 0.3(3) . . . . ?
C1 C14 C16 C10 -171.79(14) . . . . ?
C1 C14 C16 C11 11.5(2) . . . . ?
C1 C14 C13 C15 172.05(16) . . . . ?
C4 C1 C6 C9 -0.6(3) . . . . ?
C4 C1 C14 C16 47.9(2) . . . . ?
C4 C1 C14 C13 -128.56(18) . . . . ?
C6 C1 C4 C12 0.8(3) . . . . ?
C6 C1 C14 C16 -136.14(17) . . . . ?
C6 C1 C14 C13 47.4(2) . . . . ?
C10 N1 C3 C7 1.8(3) . . . . ?
C10 C16 C11 C7 2.6(2) . . . . ?
C10 C5 C15 C13 2.7(3) . . . . ?
C12 C8 C2 O1 3.2(2) . . . . ?
C12 C8 C2 O2 -177.77(17) . . . . ?
C12 C8 C9 C6 -0.1(3) . . . . ?
C14 C1 C4 C12 176.82(15) . . . . ?
C14 C1 C6 C9 -176.59(16) . . . . ?
C14 C16 C11 C7 179.40(15) . . . . ?
C14 C13 C15 C5 0.8(3) . . . . ?
C16 C10 C5 C15 -2.3(2) . . . . ?
C16 C14 C13 C15 -4.5(2) . . . . ?
C16 C11 C7 C3 0.4(3) . . . . ?
C2 C8 C12 C4 -179.95(15) . . . . ?
C2 C8 C9 C6 -179.86(15) . . . . ?
C9 C8 C12 C4 0.3(3) . . . . ?
C9 C8 C2 O1 -176.99(16) . . . . ?
C9 C8 C2 O2 2.0(3) . . . . ?
C5 C10 C16 C14 -1.4(2) . . . . ?
C5 C10 C16 C11 175.59(16) . . . . ?
C3 N1 C10 C16 1.6(2) . . . . ?
C3 N1 C10 C5 -177.75(16) . . . . ?
C13 C14 C16 C10 4.7(2) . . . . ?
C13 C14 C16 C11 -172.01(16) . . . . ?

_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_5-qpa
_database_code_depnum_ccdc_archive 'CCDC 2255889'
loop_
_audit_author_name
_audit_author_address
'longjie Wang'
;Yun nan university
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_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/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                   9.7854(5)
_cell_length_b                   10.5351(4)
_cell_length_c                   13.0707(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.184(5)
_cell_angle_gamma                90
_cell_volume                     1287.31(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8744
_cell_measurement_theta_min      2.2950
_cell_measurement_theta_max      28.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16654
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         2.304
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                2309
_reflns_number_total             3044
_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 1.5 (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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3044
_refine_ls_number_restraints     297
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.1021
_refine_ls_restrained_S_all      1.089
_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)+(0.0889P)²+2.1668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.2567
_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. Restrained distances
 O2-C1 \\sim O2-C1A
 with sigma of 0.02
 C1-C6 \\sim C1A-C6A
 with sigma of 0.02
 C1-C8 \\sim C1A-C8A
 with sigma of 0.02
 C6-C3 \\sim C6A-C3A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C12-C5 \\sim C12A-C5A
 with sigma of 0.04
 C10-C5 \\sim C10A-C5A
 with sigma of 0.02
 C16-C5 \\sim C16A-C5A
 with sigma of 0.04
 C10-N1 \\sim C10A-N1A
 with sigma of 0.02
 C10-C15 \\sim C10A-C15A
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C12-C2 \\sim C12A-C2A
 with sigma of 0.02
 C10-C7 \\sim C10A-C7A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.04
 C16-C7 \\sim C16A-C7A
 with sigma of 0.02
 C9-C3 \\sim C9A-C3A
 with sigma of 0.04
 C9-C13 \\sim C9A-C13A
 with sigma of 0.02
 C5-N1 \\sim C5A-N1A
 with sigma of 0.04
 C11-C2 \\sim C11A-C2A
 with sigma of 0.04
 C5-C11 \\sim C5A-C11A
 with sigma of 0.02
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.02
 O2-C1A \\sim O2-C1
 with sigma of 0.02
 C3-C13 \\sim C3A-C13A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.04
 C10-C2 \\sim C10A-C2A
 with sigma of 0.04
 C12-N1 \\sim C12A-N1A
 with sigma of 0.04
 C13-C7 \\sim C13A-C7A
 with sigma of 0.02
 C14-C7 \\sim C14A-C7A
 with sigma of 0.04
 C16-C13 \\sim C16A-C13A
 with sigma of 0.04
 N1-C2 \\sim N1A-C2A
 with sigma of 0.02
 C9-C7 \\sim C9A-C7A
 with sigma of 0.04
 C5-C13 \\sim C5A-C13A
 with sigma of 0.04
 C5-C15 \\sim C5A-C15A
 with sigma of 0.04
 O2-C6 \\sim O2-C6A
 with sigma of 0.04
 O2-C8 \\sim O2-C8A
 with sigma of 0.04
 C11-C7 \\sim C11A-C7A
 with sigma of 0.04
 C1-C9 \\sim C1A-C9A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C6-C13 \\sim C6A-C13A
 with sigma of 0.04
 N1-C15 \\sim N1A-C15A
 with sigma of 0.04
 C8-C13 \\sim C8A-C13A
 with sigma of 0.04
 C7A-C13A \\sim C7-C13
 with sigma of 0.02
 C10-C14 \\sim C10A-C14A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C1, C6, C8, C10, C12, C14, C16, C9, C5, C11, C3, C13, N1, C7, C15, C2, C1A,
 C6A, C8A, C10A, C12A, C14A, C16A, C9A, C5A, C11A, C3A, C13A, N1A, C7A, C15A,
 C2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C6A)=Sof(H6A)=Sof(C1A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C13A)=
 Sof(C3A)=Sof(H3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C2A)=Sof(H2A)=
 Sof(N1A)=Sof(C10A)=Sof(C5A)=Sof(C7A)=Sof(C16A)=Sof(H16A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=Sof(C1)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C13)=Sof(C3)=
 Sof(H3)=Sof(C7)=Sof(C16)=Sof(H16)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C10)=
 Sof(C5)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C2)=Sof(H2)=Sof(N1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C3(H3), C16(H16), C14(H14), C15(H15), C11(H11),
 C12(H12), C2(H2), C6A(H6A), C8A(H8A), C9A(H9A), C3A(H3A), C11A(H11A),
 C12A(H12A), C2A(H2A), C16A(H16A), C14A(H14A), C15A(H15A)
5.b Fitted hexagon refined as free rotating group:
 C6(C1,C8,C9,C13,C3), C6A(C1A,C8A,C9A,C13A,C3A)
5.c Naphthalene refined as free rotating group:
 C7(C16,C14,C15,C10,C5,C11,C12,C2,N1), C11A(C12A,C2A,N1A,C10A,C5A,C7A,C16A,
 C14A,C15A)
5.d 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 0.7827(2) 0.6076(2) 0.49646(19) 0.0458(6) Uani 1 1 d D . . . .
O1 O 0.8309(2) 0.8112(2) 0.54216(19) 0.0481(6) Uani 1 1 d . . . . .
C4 C 0.8725(3) 0.7050(3) 0.5386(2) 0.0403(7) Uani 1 1 d . . . . .
C6 C 0.5600(3) 0.6615(5) 0.5289(2) 0.0370(14) Uani 0.743(5) 1 d DG . P A 1
H6 H 0.607435 0.663875 0.601892 0.044 Uiso 0.743(5) 1 calc R U P A 1
C1 C 0.6353(3) 0.6344(7) 0.4565(3) 0.035(2) Uani 0.743(5) 1 d DG . P A 1
C8 C 0.5644(3) 0.6309(5) 0.3473(3) 0.0395(12) Uani 0.743(5) 1 d DG . P A 1
H8 H 0.614713 0.612767 0.298887 0.047 Uiso 0.743(5) 1 calc R U P A 1
C9 C 0.4182(3) 0.6546(3) 0.3107(2) 0.0353(9) Uani 0.743(5) 1 d DG . P A 1
H9 H 0.370788 0.652275 0.237646 0.042 Uiso 0.743(5) 1 calc R U P A 1
C13 C 0.3430(2) 0.6817(3) 0.3831(2) 0.0321(8) Uani 0.743(5) 1 d DG . P A 1
C3 C 0.4139(3) 0.6852(4) 0.4922(2) 0.0337(10) Uani 0.743(5) 1 d DG . P A 1
H3 H 0.363505 0.703383 0.540650 0.040 Uiso 0.743(5) 1 calc R U P A 1
C17 C 1.0239(3) 0.6606(4) 0.5775(3) 0.0525(9) Uani 1 1 d . . . . .
H17A H 1.033224 0.598821 0.633104 0.079 Uiso 1 1 calc R U . . .
H17B H 1.085425 0.731446 0.605100 0.079 Uiso 1 1 calc R U . . .
H17C H 1.050406 0.622941 0.519193 0.079 Uiso 1 1 calc R U . . .
C7 C 0.18296(18) 0.7175(2) 0.34162(18) 0.0349(8) Uani 0.743(5) 1 d DG . P A 1
C16 C 0.1504(2) 0.8290(2) 0.3863(2) 0.0384(10) Uani 0.743(5) 1 d DG . P A 1
H16 H 0.222764 0.875380 0.433738 0.046 Uiso 0.743(5) 1 calc R U P A 1
C14 C 0.0097(3) 0.8711(2) 0.3602(2) 0.0496(19) Uani 0.743(5) 1 d DG . P A 1
H14 H -0.012111 0.945728 0.390092 0.060 Uiso 0.743(5) 1 calc R U P A 1
C15 C -0.0985(2) 0.8018(2) 0.2893(2) 0.0498(12) Uani 0.743(5) 1 d DG . P A 1
H15 H -0.192637 0.830029 0.271824 0.060 Uiso 0.743(5) 1 calc R U P A 1
C10 C -0.06592(17) 0.69036(18) 0.24461(15) 0.0440(15) Uani 0.743(5) 1 d DG . P
A 1
C5 C 0.07480(17) 0.64821(16) 0.27076(14) 0.0370(9) Uani 0.743(5) 1 d DG . P A 1
C11 C 0.1074(2) 0.5367(2) 0.2261(2) 0.0399(10) Uani 0.743(5) 1 d DG . P A 1
H11 H 0.201522 0.508547 0.243552 0.048 Uiso 0.743(5) 1 calc R U P A 1
C12 C -0.0008(3) 0.4674(2) 0.1552(2) 0.0465(16) Uani 0.743(5) 1 d DG . P A 1
H12 H 0.021000 0.392844 0.125283 0.056 Uiso 0.743(5) 1 calc R U P A 1
C2 C -0.1415(3) 0.5096(2) 0.1290(2) 0.0577(13) Uani 0.743(5) 1 d DG . P A 1
H2 H -0.213877 0.463188 0.081634 0.069 Uiso 0.743(5) 1 calc R U P A 1
N1 N -0.17408(19) 0.6210(2) 0.1738(2) 0.0567(12) Uani 0.743(5) 1 d DG . P A 1
C6A C 0.5981(9) 0.6100(18) 0.3494(10) 0.043(4) Uani 0.257(5) 1 d DG . P A 2
H6A H 0.664481 0.599722 0.311827 0.051 Uiso 0.257(5) 1 calc R U P A 2
C1A C 0.6443(7) 0.631(2) 0.4594(11) 0.047(9) Uani 0.257(5) 1 d DG . P A 2
C8A C 0.5450(11) 0.6462(17) 0.5156(7) 0.040(4) Uani 0.257(5) 1 d DG . P A 2
H8A H 0.575941 0.660031 0.589129 0.048 Uiso 0.257(5) 1 calc R U P A 2
C9A C 0.3995(9) 0.6409(10) 0.4619(7) 0.034(3) Uani 0.257(5) 1 d DG . P A 2
H9A H 0.333103 0.651245 0.499530 0.040 Uiso 0.257(5) 1 calc R U P A 2
C13A C 0.3533(7) 0.6202(10) 0.3520(7) 0.033(2) Uani 0.257(5) 1 d DG . P A 2
C3A C 0.4526(10) 0.6048(11) 0.2958(7) 0.033(3) Uani 0.257(5) 1 d DG . P A 2
H3A H 0.421639 0.590937 0.222227 0.040 Uiso 0.257(5) 1 calc R U P A 2
C11A C 0.1242(7) 0.8028(7) 0.3576(6) 0.041(3) Uani 0.257(5) 1 d DG . P A 2
H11A H 0.219161 0.817481 0.396120 0.049 Uiso 0.257(5) 1 calc R U P A 2
C12A C 0.0189(9) 0.8886(7) 0.3634(8) 0.058(5) Uani 0.257(5) 1 d DG . P A 2
H12A H 0.043371 0.960735 0.405866 0.070 Uiso 0.257(5) 1 calc R U P A 2
C2A C -0.1231(8) 0.8666(7) 0.3057(8) 0.072(5) Uani 0.257(5) 1 d DG . P A 2
H2A H -0.193521 0.923990 0.309650 0.087 Uiso 0.257(5) 1 calc R U P A 2
N1A N -0.1597(6) 0.7587(7) 0.2423(7) 0.056(3) Uani 0.257(5) 1 d DG . P A 2
C10A C -0.0543(5) 0.6729(5) 0.2364(5) 0.036(4) Uani 0.257(5) 1 d DG . P A 2
C5A C 0.0876(5) 0.6949(5) 0.2941(4) 0.039(3) Uani 0.257(5) 1 d DG . P A 2
C7A C 0.1929(5) 0.6091(6) 0.2882(5) 0.034(2) Uani 0.257(5) 1 d DG . P A 2
C16A C 0.1563(7) 0.5012(6) 0.2247(7) 0.036(3) Uani 0.257(5) 1 d DG . P A 2
H16A H 0.226778 0.443811 0.220836 0.043 Uiso 0.257(5) 1 calc R U P A 2
C14A C 0.0144(8) 0.4792(6) 0.1671(7) 0.057(6) Uani 0.257(5) 1 d DG . P A 2
H14A H -0.010112 0.407062 0.124619 0.068 Uiso 0.257(5) 1 calc R U P A 2
C15A C -0.0909(6) 0.5650(6) 0.1729(6) 0.046(3) Uani 0.257(5) 1 d DG . P A 2
H15A H -0.185905 0.550312 0.134361 0.055 Uiso 0.257(5) 1 calc R U P A 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 C4 1.358(4) . ?
O2 C1 1.411(3) . ?
O2 C1A 1.320(7) . ?
O1 C4 1.196(4) . ?
C4 C17 1.492(5) . ?
C6 H6 0.9300 . ?
C6 C1 1.3900 . ?
C6 C3 1.3900 . ?
C1 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C13 1.3900 . ?
C13 C3 1.3900 . ?
C13 C7 1.545(3) . ?
C3 H3 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C7 C16 1.3900 . ?
C7 C5 1.3900 . ?
C16 H16 0.9300 . ?
C16 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C10 1.3900 . ?
C10 C5 1.3900 . ?
C10 N1 1.3900 . ?
C5 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 N1 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C1A 1.3900 . ?
C6A C3A 1.3900 . ?
C1A C8A 1.3900 . ?
C8A H8A 0.9300 . ?
C8A C9A 1.3900 . ?
C9A H9A 0.9300 . ?
C9A C13A 1.3900 . ?
C13A C3A 1.3900 . ?
C13A C7A 1.549(7) . ?
C3A H3A 0.9300 . ?
C11A H11A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A C5A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C2A N1A 1.3900 . ?
N1A C10A 1.3900 . ?
C10A C5A 1.3900 . ?
C10A C15A 1.3900 . ?
C5A C7A 1.3900 . ?
C7A C16A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C14A 1.3900 . ?
C14A H14A 0.9300 . ?
C14A C15A 1.3900 . ?
C15A H15A 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
C4 O2 C1 117.8(3) . . ?
C1A O2 C4 118.7(10) . . ?
O2 C4 C17 111.0(3) . . ?
O1 C4 O2 122.4(3) . . ?
O1 C4 C17 126.5(3) . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C3 120.0 . . ?
C3 C6 H6 120.0 . . ?
C6 C1 O2 118.6(3) . . ?
C8 C1 O2 121.4(3) . . ?
C8 C1 C6 120.0 . . ?
C1 C8 H8 120.0 . . ?
C1 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C13 120.0 . . ?
C13 C9 H9 120.0 . . ?
C9 C13 C7 119.8(2) . . ?
C3 C13 C9 120.0 . . ?
C3 C13 C7 120.0(2) . . ?
C6 C3 H3 120.0 . . ?
C13 C3 C6 120.0 . . ?
C13 C3 H3 120.0 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C7 C13 113.16(18) . . ?
C16 C7 C5 120.0 . . ?
C5 C7 C13 126.79(17) . . ?
C7 C16 H16 120.0 . . ?
C14 C16 C7 120.0 . . ?
C14 C16 H16 120.0 . . ?
C16 C14 H14 120.0 . . ?
C15 C14 C16 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C10 C15 H15 120.0 . . ?
C15 C10 C5 120.0 . . ?
C15 C10 N1 120.0 . . ?
C5 C10 N1 120.0 . . ?
C10 C5 C7 120.0 . . ?
C11 C5 C7 120.0 . . ?
C11 C5 C10 120.0 . . ?
C5 C11 H11 120.0 . . ?
C12 C11 C5 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C2 120.0 . . ?
C2 C12 H12 120.0 . . ?
C12 C2 H2 120.0 . . ?
N1 C2 C12 120.0 . . ?
N1 C2 H2 120.0 . . ?
C2 N1 C10 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C1A C6A C3A 120.0 . . ?
C3A C6A H6A 120.0 . . ?
O2 C1A C6A 109.6(9) . . ?
O2 C1A C8A 129.0(9) . . ?
C8A C1A C6A 120.0 . . ?
C1A C8A H8A 120.0 . . ?
C1A C8A C9A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C13A C9A C8A 120.0 . . ?
C13A C9A H9A 120.0 . . ?
C9A C13A C3A 120.0 . . ?
C9A C13A C7A 122.5(6) . . ?
C3A C13A C7A 117.5(6) . . ?
C6A C3A H3A 120.0 . . ?
C13A C3A C6A 120.0 . . ?
C13A C3A H3A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C5A 120.0 . . ?
C5A C11A H11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C2A C12A C11A 120.0 . . ?
C2A C12A H12A 120.0 . . ?
C12A C2A H2A 120.0 . . ?
N1A C2A C12A 120.0 . . ?
N1A C2A H2A 120.0 . . ?
C2A N1A C10A 120.0 . . ?
N1A C10A C5A 120.0 . . ?
N1A C10A C15A 120.0 . . ?
C5A C10A C15A 120.0 . . ?
C10A C5A C11A 120.0 . . ?
C7A C5A C11A 120.0 . . ?
C7A C5A C10A 120.0 . . ?
C5A C7A C13A 124.8(5) . . ?
C5A C7A C16A 120.0 . . ?
C16A C7A C13A 115.1(5) . . ?
C7A C16A H16A 120.0 . . ?
C14A C16A C7A 120.0 . . ?
C14A C16A H16A 120.0 . . ?
C16A C14A H14A 120.0 . . ?
C16A C14A C15A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C10A C15A H15A 120.0 . . ?
C14A C15A C10A 120.0 . . ?
C14A C15A H15A 120.0 . . ?

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
O2 C1 C8 C9 178.3(5) . . . . ?
O2 C1A C8A C9A -165(2) . . . . ?
C4 O2 C1 C6 -71.5(4) . . . . ?
C4 O2 C1 C8 110.1(3) . . . . ?
C4 O2 C1A C6A 115.1(6) . . . . ?
C4 O2 C1A C8A -78.5(15) . . . . ?
C6 C1 C8 C9 0.0 . . . . ?
C1 O2 C4 O1 -0.4(5) . . . . ?
C1 O2 C4 C17 179.8(3) . . . . ?
C1 C6 C3 C13 0.0 . . . . ?
C1 C8 C9 C13 0.0 . . . . ?
C8 C9 C13 C3 0.0 . . . . ?
C8 C9 C13 C7 175.6(3) . . . . ?
C9 C13 C3 C6 0.0 . . . . ?
C9 C13 C7 C16 -128.6(2) . . . . ?
C9 C13 C7 C5 54.1(3) . . . . ?
C13 C7 C16 C14 -177.5(2) . . . . ?
C13 C7 C5 C10 177.1(3) . . . . ?
C13 C7 C5 C11 -2.9(3) . . . . ?
C3 C6 C1 O2 -178.4(5) . . . . ?
C3 C6 C1 C8 0.0 . . . . ?
C3 C13 C7 C16 46.9(3) . . . . ?
C3 C13 C7 C5 -130.3(2) . . . . ?
C7 C13 C3 C6 -175.6(3) . . . . ?
C7 C16 C14 C15 0.0 . . . . ?
C7 C5 C11 C12 180.0 . . . . ?
C16 C7 C5 C10 0.0 . . . . ?
C16 C7 C5 C11 180.0 . . . . ?
C16 C14 C15 C10 0.0 . . . . ?
C14 C15 C10 C5 0.0 . . . . ?
C14 C15 C10 N1 180.0 . . . . ?
C15 C10 C5 C7 0.0 . . . . ?
C15 C10 C5 C11 180.0 . . . . ?
C15 C10 N1 C2 180.0 . . . . ?
C10 C5 C11 C12 0.0 . . . . ?
C5 C7 C16 C14 0.0 . . . . ?
C5 C10 N1 C2 0.0 . . . . ?
C5 C11 C12 C2 0.0 . . . . ?
C11 C12 C2 N1 0.0 . . . . ?
C12 C2 N1 C10 0.0 . . . . ?
N1 C10 C5 C7 180.0 . . . . ?
N1 C10 C5 C11 0.0 . . . . ?
C6A C1A C8A C9A 0.0 . . . . ?
C1A O2 C4 O1 -0.9(9) . . . . ?
C1A O2 C4 C17 179.3(8) . . . . ?
C1A C6A C3A C13A 0.0 . . . . ?
C1A C8A C9A C13A 0.0 . . . . ?
C8A C9A C13A C3A 0.0 . . . . ?
C8A C9A C13A C7A 178.0(11) . . . . ?
C9A C13A C3A C6A 0.0 . . . . ?
C9A C13A C7A C5A 50.0(9) . . . . ?
C9A C13A C7A C16A -127.5(7) . . . . ?
C13A C7A C16A C14A 177.6(6) . . . . ?
C3A C6A C1A O2 167.8(17) . . . . ?
C3A C6A C1A C8A 0.0 . . . . ?
C3A C13A C7A C5A -131.9(6) . . . . ?
C3A C13A C7A C16A 50.5(8) . . . . ?
C11A C12A C2A N1A 0.0 . . . . ?
C11A C5A C7A C13A 2.6(7) . . . . ?
C11A C5A C7A C16A 180.0 . . . . ?
C12A C11A C5A C10A 0.0 . . . . ?
C12A C11A C5A C7A 180.0 . . . . ?
C12A C2A N1A C10A 0.0 . . . . ?
C2A N1A C10A C5A 0.0 . . . . ?
C2A N1A C10A C15A 180.0 . . . . ?
N1A C10A C5A C11A 0.0 . . . . ?
N1A C10A C5A C7A 180.0 . . . . ?
N1A C10A C15A C14A 180.0 . . . . ?
C10A C5A C7A C13A -177.4(7) . . . . ?
C10A C5A C7A C16A 0.0 . . . . ?
C5A C11A C12A C2A 0.0 . . . . ?
C5A C10A C15A C14A 0.0 . . . . ?
C5A C7A C16A C14A 0.0 . . . . ?
C7A C13A C3A C6A -178.1(11) . . . . ?
C7A C16A C14A C15A 0.0 . . . . ?
C16A C14A C15A C10A 0.0 . . . . ?
C15A C10A C5A C11A 180.0 . . . . ?
C15A C10A C5A C7A 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
