# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cu_20230922_ys_nlg_hhr_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2308721'
loop_
_audit_author_name
_audit_author_address
'Haoran Hu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   13.6284(3)
_cell_length_b                   13.6284(3)
_cell_length_c                   5.4093(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     870.08(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1761
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.743
_cell_measurement_theta_min      3.745
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0867 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.7897.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7186
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.188
_diffrn_reflns_theta_min         3.745
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.785
_reflns_Friedel_fraction_max     0.782
_reflns_number_gt                1643
_reflns_number_total             1906
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.117
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1906
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.017
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C2(H2), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11),
 C12(H12), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.7932(2) 0.6211(2) 0.9102(5) 0.0560(7) Uani 1 1 d . . . . .
H1 H 0.743630 0.581391 0.805365 0.084 Uiso 1 1 calc R U . . .
N1 N 0.54995(19) 0.38037(18) 0.0978(5) 0.0394(6) Uani 1 1 d . . . . .
H1A H 0.547901 0.321337 0.026447 0.047 Uiso 1 1 calc R U . . .
N2 N 0.61415(18) 0.43410(19) 0.2968(5) 0.0383(6) Uani 1 1 d . . . . .
N3 N 0.6556(2) 0.58556(19) 0.5502(5) 0.0385(6) Uani 1 1 d . . . . .
C1 C 0.4621(2) 0.5849(2) 0.1444(6) 0.0398(7) Uani 1 1 d . . . . .
H1B H 0.476527 0.645496 0.252843 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3899(2) 0.5596(3) -0.0532(7) 0.0437(7) Uani 1 1 d . . . . .
H2 H 0.355291 0.604210 -0.082316 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3662(2) 0.4688(3) -0.2134(6) 0.0429(7) Uani 1 1 d . . . . .
H3 H 0.315759 0.453284 -0.348030 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4142(2) 0.4024(2) -0.1794(6) 0.0406(7) Uani 1 1 d . . . . .
H4 H 0.397885 0.340985 -0.286854 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4883(2) 0.4290(2) 0.0203(6) 0.0353(6) Uani 1 1 d . . . . .
C6 C 0.5141(2) 0.5195(2) 0.1831(6) 0.0336(6) Uani 1 1 d . . . . .
C7 C 0.5948(2) 0.5180(2) 0.3516(6) 0.0348(6) Uani 1 1 d . . . . .
C8 C 0.6557(2) 0.6769(2) 0.6095(6) 0.0407(7) Uani 1 1 d . . . . .
H8 H 0.611499 0.699531 0.515768 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7214(2) 0.7458(2) 0.8151(6) 0.0397(7) Uani 1 1 d . . . . .
C10 C 0.7200(3) 0.8454(3) 0.8760(7) 0.0533(9) Uani 1 1 d . . . . .
H10 H 0.675011 0.866855 0.781200 0.064 Uiso 1 1 calc R U . . .
C11 C 0.7826(3) 0.9122(3) 1.0704(8) 0.0561(9) Uani 1 1 d . . . . .
H11 H 0.782076 0.980094 1.107638 0.067 Uiso 1 1 calc R U . . .
C12 C 0.8466(3) 0.8801(3) 1.2121(7) 0.0548(9) Uani 1 1 d . . . . .
H12 H 0.889769 0.926222 1.346755 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8483(3) 0.7825(3) 1.1601(7) 0.0520(9) Uani 1 1 d . . . . .
H13 H 0.891303 0.760749 1.260787 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7871(2) 0.7150(3) 0.9598(6) 0.0428(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C14 1.351(4) . ?
N1 H1A 0.8800 . ?
N1 N2 1.349(3) . ?
N1 C5 1.371(3) . ?
N2 C7 1.329(3) . ?
N3 C7 1.387(4) . ?
N3 C8 1.284(3) . ?
C1 H1B 0.9500 . ?
C1 C2 1.375(4) . ?
C1 C6 1.405(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(4) . ?
C5 C6 1.409(4) . ?
C6 C7 1.437(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.442(4) . ?
C9 C10 1.407(4) . ?
C9 C14 1.403(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(5) . ?

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 O1 H1 109.5 . . ?
N2 N1 H1A 124.2 . . ?
N2 N1 C5 111.7(2) . . ?
C5 N1 H1A 124.2 . . ?
C7 N2 N1 106.9(2) . . ?
C8 N3 C7 123.2(3) . . ?
C2 C1 H1B 120.6 . . ?
C2 C1 C6 118.8(3) . . ?
C6 C1 H1B 120.6 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.5 . . ?
C3 C4 C5 117.1(3) . . ?
C5 C4 H4 121.5 . . ?
N1 C5 C4 130.5(3) . . ?
N1 C5 C6 106.7(3) . . ?
C4 C5 C6 122.8(3) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 137.4(3) . . ?
C5 C6 C7 104.0(2) . . ?
N2 C7 N3 115.8(2) . . ?
N2 C7 C6 110.7(3) . . ?
N3 C7 C6 133.5(2) . . ?
N3 C8 H8 119.2 . . ?
N3 C8 C9 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 120.4(3) . . ?
C14 C9 C8 121.1(2) . . ?
C14 C9 C10 118.5(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
O1 C14 C9 121.6(3) . . ?
O1 C14 C13 118.7(3) . . ?
C13 C14 C9 119.7(3) . . ?

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 N2 C7 N3 -178.7(2) . . . . ?
N1 N2 C7 C6 0.3(3) . . . . ?
N1 C5 C6 C1 179.7(2) . . . . ?
N1 C5 C6 C7 0.8(3) . . . . ?
N2 N1 C5 C4 178.2(3) . . . . ?
N2 N1 C5 C6 -0.7(3) . . . . ?
N3 C8 C9 C10 180.0(3) . . . . ?
N3 C8 C9 C14 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C6 C7 N2 -179.3(3) . . . . ?
C1 C6 C7 N3 -0.6(6) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C6 C7 177.2(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 N1 -178.6(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -178.2(3) . . . . ?
C5 N1 N2 C7 0.2(3) . . . . ?
C5 C6 C7 N2 -0.7(3) . . . . ?
C5 C6 C7 N3 178.0(3) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C7 N3 C8 C9 -179.0(3) . . . . ?
C8 N3 C7 N2 172.2(3) . . . . ?
C8 N3 C7 C6 -6.4(5) . . . . ?
C8 C9 C10 C11 -179.6(3) . . . . ?
C8 C9 C14 O1 1.2(4) . . . . ?
C8 C9 C14 C13 -178.9(3) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C9 C14 O1 -179.3(3) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 O1 178.3(3) . . . . ?
C12 C13 C14 C9 -1.6(5) . . . . ?
C14 C9 C10 C11 0.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20230922_ys_nlg_hhr_6_0m
_database_code_depnum_ccdc_archive 'CCDC 2308722'
loop_
_audit_author_name
_audit_author_address
'Haoran Hu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_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 0.0033 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                   14.3901(6)
_cell_length_b                   5.6092(3)
_cell_length_c                   15.9163(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.169(2)
_cell_angle_gamma                90
_cell_volume                     1162.74(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.090
_cell_measurement_theta_min      3.955
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9367.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12070
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.828
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                1924
_reflns_number_total             2645
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.227
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.042
_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)+(0.0511P)²+0.2951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1A), C2(H2A), C3(H3), C4(H4), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.30316(8) 0.17735(19) 0.31215(7) 0.0349(3) Uani 1 1 d . . . . .
H1 H 0.363602 0.225938 0.342193 0.052 Uiso 1 1 calc R U . . .
N1 N 0.46015(9) 0.4498(2) 0.35587(8) 0.0282(3) Uani 1 1 d . . . . .
N2 N 0.78064(9) 0.1998(2) 0.61086(8) 0.0326(3) Uani 1 1 d . . . . .
H2 H 0.763391 0.065241 0.628872 0.039 Uiso 1 1 calc R U . . .
C1 C 0.23808(12) 0.7132(3) 0.16696(10) 0.0309(3) Uani 1 1 d . . . . .
H1A H 0.269324 0.855001 0.158726 0.037 Uiso 1 1 calc R U . . .
C2 C 0.13577(12) 0.6722(3) 0.11118(10) 0.0337(4) Uani 1 1 d . . . . .
H2A H 0.096773 0.784594 0.064962 0.040 Uiso 1 1 calc R U . . .
C3 C 0.09007(12) 0.4635(3) 0.12337(10) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.019454 0.434437 0.085323 0.040 Uiso 1 1 calc R U . . .
C4 C 0.14644(11) 0.2990(3) 0.19017(10) 0.0320(3) Uani 1 1 d . . . . .
H4 H 0.114638 0.156984 0.197444 0.038 Uiso 1 1 calc R U . . .
C5 C 0.24936(11) 0.3404(2) 0.24665(9) 0.0272(3) Uani 1 1 d . . . . .
C6 C 0.29686(11) 0.5504(2) 0.23543(9) 0.0267(3) Uani 1 1 d . . . . .
C7 C 0.40404(11) 0.5990(3) 0.29357(10) 0.0290(3) Uani 1 1 d . . . . .
H7 H 0.433511 0.743906 0.285556 0.035 Uiso 1 1 calc R U . . .
C8 C 0.56524(11) 0.4884(3) 0.41465(10) 0.0267(3) Uani 1 1 d . . . . .
C9 C 0.61268(11) 0.3145(3) 0.48122(10) 0.0283(3) Uani 1 1 d . . . . .
H9 H 0.575480 0.179732 0.486411 0.034 Uiso 1 1 calc R U . . .
C10 C 0.71603(11) 0.3428(3) 0.54008(9) 0.0273(3) Uani 1 1 d . . . . .
C11 C 0.77412(11) 0.5399(3) 0.53385(10) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.72434(11) 0.7137(3) 0.46633(10) 0.0306(3) Uani 1 1 d . . . . .
H12 H 0.761230 0.848640 0.460811 0.037 Uiso 1 1 calc R U . . .
C13 C 0.62208(11) 0.6881(3) 0.40819(10) 0.0309(3) Uani 1 1 d . . . . .
H13 H 0.588749 0.806817 0.362679 0.037 Uiso 1 1 calc R U . . .
C14 C 0.87604(12) 0.5072(3) 0.60390(10) 0.0346(4) Uani 1 1 d . . . . .
H14 H 0.932944 0.609997 0.616719 0.042 Uiso 1 1 calc R U . . .
C15 C 0.87617(12) 0.3009(3) 0.64877(10) 0.0356(4) Uani 1 1 d . . . . .
H15 H 0.934218 0.236364 0.699163 0.043 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 0.8400 . ?
O1 C5 1.3553(17) . ?
N1 C7 1.2863(18) . ?
N1 C8 1.4162(18) . ?
N2 H2 0.8800 . ?
N2 C10 1.3731(18) . ?
N2 C15 1.367(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.377(2) . ?
C1 C6 1.3974(19) . ?
C2 H2A 0.9500 . ?
C2 C3 1.396(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 C6 1.411(2) . ?
C6 C7 1.448(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3872(19) . ?
C8 C13 1.417(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 C11 1.415(2) . ?
C11 C12 1.401(2) . ?
C11 C14 1.427(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.359(2) . ?
C15 H15 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
C5 O1 H1 109.5 . . ?
C7 N1 C8 123.63(13) . . ?
C10 N2 H2 125.6 . . ?
C15 N2 H2 125.6 . . ?
C15 N2 C10 108.83(13) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C6 121.35(14) . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 H2A 120.4 . . ?
C1 C2 C3 119.21(14) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.68(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(14) . . ?
C5 C4 H4 119.9 . . ?
O1 C5 C4 119.26(13) . . ?
O1 C5 C6 120.79(13) . . ?
C4 C5 C6 119.95(13) . . ?
C1 C6 C5 118.62(13) . . ?
C1 C6 C7 120.16(13) . . ?
C5 C6 C7 121.22(13) . . ?
N1 C7 C6 121.26(13) . . ?
N1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N1 C8 C13 124.06(13) . . ?
C9 C8 N1 115.95(13) . . ?
C9 C8 C13 119.99(13) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.22(13) . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 130.08(14) . . ?
N2 C10 C11 107.44(13) . . ?
C9 C10 C11 122.48(13) . . ?
C10 C11 C14 106.63(13) . . ?
C12 C11 C10 118.21(13) . . ?
C12 C11 C14 135.15(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(13) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.34(14) . . ?
C12 C13 H13 119.3 . . ?
C11 C14 H14 126.5 . . ?
C15 C14 C11 106.93(14) . . ?
C15 C14 H14 126.5 . . ?
N2 C15 H15 124.9 . . ?
C14 C15 N2 110.16(14) . . ?
C14 C15 H15 124.9 . . ?

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 C5 C6 C1 -179.94(12) . . . . ?
O1 C5 C6 C7 -0.3(2) . . . . ?
N1 C8 C9 C10 179.41(12) . . . . ?
N1 C8 C13 C12 -178.97(13) . . . . ?
N2 C10 C11 C12 -179.60(12) . . . . ?
N2 C10 C11 C14 0.14(15) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C6 C7 N1 -178.70(13) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 -179.49(13) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 O1 179.61(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 179.76(13) . . . . ?
C5 C6 C7 N1 1.7(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C7 N1 C8 C9 176.73(13) . . . . ?
C7 N1 C8 C13 -3.8(2) . . . . ?
C8 N1 C7 C6 -179.94(12) . . . . ?
C8 C9 C10 N2 -179.99(14) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C9 C10 C11 C14 -179.37(13) . . . . ?
C10 N2 C15 C14 -0.43(17) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C14 C15 -0.40(16) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C11 C14 C15 N2 0.51(17) . . . . ?
C12 C11 C14 C15 179.28(16) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
C14 C11 C12 C13 179.88(15) . . . . ?
C15 N2 C10 C9 179.63(14) . . . . ?
C15 N2 C10 C11 0.16(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_mo_20230922_ys_nlg_hhr_7_0m
_database_code_depnum_ccdc_archive 'CCDC 2308723'
loop_
_audit_author_name
_audit_author_address
'Haoran Hu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.3409(5)
_cell_length_b                   21.7821(13)
_cell_length_c                   7.6787(5)
_cell_angle_alpha                90
_cell_angle_beta                 120.072(2)
_cell_angle_gamma                90
_cell_volume                     1207.30(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.155
_cell_measurement_theta_min      3.741
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1649 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9536.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8497
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_min         3.742
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                1913
_reflns_number_total             1999
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.133
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.067
_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)+(0.0420P)²+0.1878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0814
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1A), C2(H2A), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.5780(2) 0.54074(7) 0.4565(3) 0.0433(5) Uani 1 1 d . . . . .
H1 H 0.616354 0.504492 0.467320 0.065 Uiso 1 1 calc R U . . .
N1 N 0.5730(3) 0.42200(8) 0.4845(3) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.7807(3) 0.37238(9) 0.2908(3) 0.0400(5) Uani 1 1 d . . . . .
H2 H 0.728680 0.406996 0.229388 0.048 Uiso 1 1 calc R U . . .
C1 C 0.1460(3) 0.48820(12) 0.4226(4) 0.0417(6) Uani 1 1 d . . . . .
H1A H 0.087806 0.451408 0.428678 0.050 Uiso 1 1 calc R U . . .
C2 C 0.0556(4) 0.54369(13) 0.3948(4) 0.0479(7) Uani 1 1 d . . . . .
H2A H -0.064334 0.544897 0.380330 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1407(4) 0.59735(12) 0.3881(4) 0.0467(7) Uani 1 1 d . . . . .
H3 H 0.079306 0.635534 0.370217 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3137(4) 0.59593(11) 0.4072(4) 0.0445(7) Uani 1 1 d . . . . .
H4 H 0.370649 0.633090 0.401784 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4055(3) 0.54043(9) 0.4344(4) 0.0349(5) Uani 1 1 d . . . . .
C6 C 0.3216(3) 0.48542(10) 0.4419(4) 0.0336(5) Uani 1 1 d . . . . .
C7 C 0.4153(3) 0.42697(10) 0.4748(3) 0.0342(5) Uani 1 1 d . . . . .
H7 H 0.358307 0.391141 0.489599 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6682(3) 0.36519(10) 0.5384(3) 0.0304(5) Uani 1 1 d . . . . .
C9 C 0.6811(3) 0.32867(11) 0.6929(4) 0.0375(6) Uani 1 1 d . . . . .
H9 H 0.617928 0.340663 0.761583 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7852(4) 0.27450(11) 0.7494(4) 0.0427(6) Uani 1 1 d . . . . .
H10 H 0.791494 0.250499 0.855984 0.051 Uiso 1 1 calc R U . . .
C11 C 0.8785(3) 0.25529(10) 0.6544(4) 0.0417(6) Uani 1 1 d . . . . .
H11 H 0.947819 0.218226 0.693639 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8699(3) 0.29100(10) 0.4994(4) 0.0372(6) Uani 1 1 d . . . . .
C13 C 0.7659(3) 0.34619(9) 0.4443(3) 0.0314(5) Uani 1 1 d . . . . .
C14 C 0.9467(4) 0.28608(12) 0.3714(4) 0.0521(7) Uani 1 1 d . . . . .
H14 H 1.023722 0.253789 0.372269 0.062 Uiso 1 1 calc R U . . .
C15 C 0.8913(4) 0.33518(13) 0.2488(5) 0.0530(7) Uani 1 1 d . . . . .
H15 H 0.923325 0.343109 0.148411 0.064 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 0.8400 . ?
O1 C5 1.362(3) . ?
N1 C7 1.283(3) . ?
N1 C8 1.416(3) . ?
N2 H2 0.8800 . ?
N2 C13 1.370(3) . ?
N2 C15 1.382(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(4) . ?
C1 C6 1.397(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.449(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(3) . ?
C8 C13 1.396(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.372(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 C13 1.417(3) . ?
C12 C14 1.421(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.344(4) . ?
C15 H15 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
C5 O1 H1 109.5 . . ?
C7 N1 C8 119.93(18) . . ?
C13 N2 H2 125.8 . . ?
C13 N2 C15 108.4(2) . . ?
C15 N2 H2 125.8 . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C6 121.0(3) . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
O1 C5 C4 118.9(2) . . ?
O1 C5 C6 121.13(19) . . ?
C4 C5 C6 120.0(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 120.1(2) . . ?
C5 C6 C7 121.4(2) . . ?
N1 C7 C6 122.2(2) . . ?
N1 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C9 C8 N1 122.9(2) . . ?
C9 C8 C13 117.23(19) . . ?
C13 C8 N1 119.69(19) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 C14 134.5(2) . . ?
C13 C12 C14 106.2(2) . . ?
N2 C13 C8 130.55(19) . . ?
N2 C13 C12 107.71(19) . . ?
C8 C13 C12 121.7(2) . . ?
C12 C14 H14 126.0 . . ?
C15 C14 C12 107.9(2) . . ?
C15 C14 H14 126.0 . . ?
N2 C15 H15 125.1 . . ?
C14 C15 N2 109.8(2) . . ?
C14 C15 H15 125.1 . . ?

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 C5 C6 C1 178.6(2) . . . . ?
O1 C5 C6 C7 0.4(3) . . . . ?
N1 C8 C9 C10 -176.3(2) . . . . ?
N1 C8 C13 N2 -4.2(3) . . . . ?
N1 C8 C13 C12 177.22(19) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C6 C7 N1 176.9(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 O1 -178.8(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 N1 -5.0(3) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C7 N1 C8 C9 -42.7(3) . . . . ?
C7 N1 C8 C13 142.2(2) . . . . ?
C8 N1 C7 C6 173.2(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C8 C13 N2 -179.6(2) . . . . ?
C9 C8 C13 C12 1.8(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C10 C11 C12 C14 179.6(3) . . . . ?
C11 C12 C13 N2 179.7(2) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
C11 C12 C14 C15 -179.5(3) . . . . ?
C12 C14 C15 N2 0.0(3) . . . . ?
C13 N2 C15 C14 0.1(3) . . . . ?
C13 C8 C9 C10 -1.1(3) . . . . ?
C13 C12 C14 C15 -0.1(3) . . . . ?
C14 C12 C13 N2 0.1(2) . . . . ?
C14 C12 C13 C8 179.0(2) . . . . ?
C15 N2 C13 C8 -178.9(2) . . . . ?
C15 N2 C13 C12 -0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
