# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_a230421c
_database_code_depnum_ccdc_archive 'CCDC 2288452'
loop_
_audit_author_name
_audit_author_address
'En-Cui Yang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-04-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N2 O'
_chemical_formula_sum            'C8 H6 N2 O'
_chemical_formula_weight         146.15
_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      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                   3.7377(3)
_cell_length_b                   15.2421(11)
_cell_length_c                   12.2673(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.345(7)
_cell_angle_gamma                90
_cell_volume                     694.59(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    819
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      72.8530
_cell_measurement_theta_min      4.6450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2281
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         4.644
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  32.00   1.00    1.00    --  -41.42  57.00-180.00   95
  2  ω     34.00  95.00   1.00    1.00    --   41.42-125.00 -30.00   61
  3  ω     12.00  50.00   1.00    1.00    --   41.42 -38.00 -60.00   38
  4  ω    133.00 178.00   1.00    2.25    --  105.20  77.00 -60.00   45
  5  ω    110.00 174.00   1.00    2.25    --  105.20  77.00 -30.00   64
  6  ω     99.00 124.00   1.00    2.25    --  105.20 125.00  60.00   25
  7  ω     95.00 177.00   1.00    2.25    --  105.20  61.00 120.00   82
  8  ω    106.00 163.00   1.00    2.25    --  105.20  77.00-120.00   57
  9  ω     41.00  67.00   1.00    2.25    --  105.20 -61.00-150.00   26
 10  ω     69.00 122.00   1.00    2.25    --  105.20 -61.00-150.00   53
 11  ω     37.00  62.00   1.00    2.25    --  105.20 -45.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365223000
_diffrn_orient_matrix_UB_12      -0.0210745000
_diffrn_orient_matrix_UB_13      -0.1210450000
_diffrn_orient_matrix_UB_21      -0.2003281000
_diffrn_orient_matrix_UB_22      0.0855456000
_diffrn_orient_matrix_UB_23      -0.0349281000
_diffrn_orient_matrix_UB_31      0.3611668000
_diffrn_orient_matrix_UB_32      0.0496837000
_diffrn_orient_matrix_UB_33      0.0090153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1006
_reflns_number_total             1248
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.058
_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)+(0.0739P)²+0.0376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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 0.8963(3) 0.88895(8) 0.45008(10) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.7575(4) 0.94913(9) 0.60788(12) 0.0244(4) Uani 1 1 d . . . . .
H1A H 0.839926 0.999615 0.591736 0.029 Uiso 1 1 calc R U . . .
H1B H 0.667283 0.941867 0.668764 0.029 Uiso 1 1 calc R U . . .
N2 N 0.1184(4) 0.47972(10) 0.67501(13) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.6278(4) 0.79505(11) 0.57250(14) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.5896(5) 0.77431(11) 0.68068(14) 0.0215(4) Uani 1 1 d . . . . .
H2 H 0.648289 0.815804 0.735320 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4649(5) 0.69245(12) 0.70842(14) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.443734 0.678485 0.781221 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3721(4) 0.63162(11) 0.62562(14) 0.0210(4) Uani 1 1 d . . . . .
C5 C 0.4091(5) 0.65121(12) 0.51628(14) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.346960 0.610145 0.461366 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5399(5) 0.73284(11) 0.49100(14) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.569248 0.746251 0.418572 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7697(4) 0.88234(11) 0.53872(14) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.2320(5) 0.54686(11) 0.65329(14) 0.0223(4) 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 C7 1.237(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.329(2) . ?
N2 C8 1.150(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.391(2) . ?
C1 C7 1.507(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 C5 1.396(2) . ?
C4 C8 1.448(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 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
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
C2 C1 C6 119.42(16) . . ?
C2 C1 C7 122.75(16) . . ?
C6 C1 C7 117.82(14) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.84(16) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.94(16) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 121.07(16) . . ?
C3 C4 C8 119.41(15) . . ?
C5 C4 C8 119.52(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.84(16) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.87(15) . . ?
C5 C6 H6 119.6 . . ?
O1 C7 N1 122.82(15) . . ?
O1 C7 C1 119.60(15) . . ?
N1 C7 C1 117.57(14) . . ?
N2 C8 C4 179.5(2) . . ?

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
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C1 C7 O1 158.93(16) . . . . ?
C2 C1 C7 N1 -19.9(2) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 C8 -178.26(15) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C6 C1 C7 O1 -19.7(2) . . . . ?
C6 C1 C7 N1 161.40(16) . . . . ?
C7 C1 C2 C3 -178.65(15) . . . . ?
C7 C1 C6 C5 179.82(15) . . . . ?
C8 C4 C5 C6 179.33(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.693
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# 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_a230602a
_database_code_depnum_ccdc_archive 'CCDC 2288453'
loop_
_audit_author_name
_audit_author_address
'En-Cui Yang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2023-08-14 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-08-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N2 O'
_chemical_formula_sum            'C8 H6 N2 O'
_chemical_formula_weight         146.15
_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      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                   7.1484(13)
_cell_length_b                   10.7108(13)
_cell_length_c                   9.9789(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.365(19)
_cell_angle_gamma                90
_cell_volume                     729.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3290
_cell_measurement_theta_min      7.7130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2593
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         6.218
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -22.00   1.00    1.48    --  -41.42 -38.00 120.00   94
  2  ω     32.00  96.00   1.00    1.48    --   41.42-125.00 -30.00   64
  3  ω     29.00  56.00   1.00    1.48    --   41.42 -99.00-180.00   27
  4  ω     49.00  76.00   1.00    1.48    --   41.42-125.00-180.00   27
  5  ω    104.00 178.00   1.00    5.93    --  105.20  77.00-150.00   74
  6  ω    104.00 171.00   1.00    5.93    --  105.20  77.00   0.00   67
  7  ω     26.00  88.00   1.00    5.93    --  105.20 -94.00  30.00   62
  8  ω     69.00  99.00   1.00    5.93    --  105.20-125.00   0.00   30
  9  ω    112.00 138.00   1.00    5.93    --  105.20  77.00  60.00   26
 10  ω    109.00 173.00   1.00    5.93    --  105.20  77.00  90.00   64
 11  ω    116.00 178.00   1.00    5.93    --  105.20  30.00 150.00   62
 12  ω    120.00 146.00   1.00    5.93    --  105.20 125.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1160273000
_diffrn_orient_matrix_UB_12      0.1222522000
_diffrn_orient_matrix_UB_13      0.0412917000
_diffrn_orient_matrix_UB_21      -0.1471487000
_diffrn_orient_matrix_UB_22      0.0444257000
_diffrn_orient_matrix_UB_23      0.0754172000
_diffrn_orient_matrix_UB_31      0.1264252000
_diffrn_orient_matrix_UB_32      -0.0611663000
_diffrn_orient_matrix_UB_33      0.1371175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                902
_reflns_number_total             1301
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1301
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      1.071
_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)+(0.1385P)²+0.1006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C7-C1 = C7A-C1A
 1.53 with sigma of 0.01
 C8-C4 = C8A-C4A
 1.38 with sigma of 0.01
 N2A-C8A = N2-C8
 1.16 with sigma of 0.01
 O1-C7 = O0-C7A
 1.22 with sigma of 0.01
 N1-C7 = N1A-C7A
 1.3 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O0)
Uanis(C7) = Uanis(C7A)
Uanis(N1) = Uanis(N1A)
Uanis(C1) = Uanis(C1A)
Uanis(C6A) = Uanis(C6)
Uanis(C5A) = Uanis(C5)
Uanis(C4) = Uanis(C4A)
Uanis(C3) = Uanis(C3A)
Uanis(C2) = Uanis(C2A)
Uanis(C8A) = Uanis(C8)
Uanis(N2) = Uanis(N2A)
4. Others
 Sof(C8A)=Sof(N2A)=Sof(C1A)=Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=
 Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C7A)=Sof(O0)=Sof(N1A)=Sof(H1AA)=
 Sof(H1AB)=1-FVAR(1)
 Sof(O1)=Sof(C1)=Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(C3)=Sof(H3)=
 Sof(C2)=Sof(H2)=Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(C7)=Sof(N2)=Sof(C8)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C2(H2), C6A(H6A), C5A(H5A), C3A(H3A), C2A(H2A)
5.b Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2), C1A(C6A,C5A,C4A,C3A,C2A)
5.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N1A(H1AA,H1AB)
;
_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 0.2275(4) 0.2442(2) 0.3405(2) 0.0593(8) Uani 0.758(2) 1 d D . P A 1
C1 C 0.2441(5) 0.42292(13) 0.4840(2) 0.0319(9) Uani 0.758(2) 1 d D . P A 1
C6 C 0.3202(5) 0.47352(16) 0.61752(18) 0.0389(9) Uani 0.758(2) 1 d G . P A 1
H6 H 0.367635 0.421238 0.694631 0.047 Uiso 0.758(2) 1 calc R . P A 1
C5 C 0.3253(5) 0.60226(17) 0.63580(17) 0.0436(9) Uani 0.758(2) 1 d G . P A 1
H5 H 0.376151 0.636119 0.725131 0.052 Uiso 0.758(2) 1 calc R . P A 1
C4 C 0.2543(5) 0.68041(13) 0.5206(2) 0.0390(9) Uani 0.758(2) 1 d DG . P A 1
C3 C 0.1783(5) 0.62981(17) 0.38704(18) 0.0440(9) Uani 0.758(2) 1 d G . P A 1
H3 H 0.130834 0.682091 0.309931 0.053 Uiso 0.758(2) 1 calc R . P A 1
C2 C 0.1732(5) 0.50106(18) 0.36876(17) 0.0408(9) Uani 0.758(2) 1 d G . P A 1
H2 H 0.122316 0.467210 0.279428 0.049 Uiso 0.758(2) 1 calc R . P A 1
N1 N 0.2623(4) 0.2090(2) 0.5660(3) 0.0511(8) Uani 0.758(2) 1 d D . P A 1
H1A H 0.263305 0.129530 0.553999 0.061 Uiso 0.758(2) 1 calc R . P A 1
H1B H 0.273363 0.238979 0.647988 0.061 Uiso 0.758(2) 1 calc R . P A 1
C7 C 0.2437(4) 0.2848(2) 0.4590(3) 0.0379(7) Uani 0.758(2) 1 d D . P A 1
N2 N 0.2648(6) 0.9199(3) 0.5454(4) 0.0792(12) Uani 0.758(2) 1 d D . P A 1
C8 C 0.2600(6) 0.8134(3) 0.5340(4) 0.0565(10) Uani 0.758(2) 1 d D . P A 1
C8A C 0.238(2) 0.8107(7) 0.4623(14) 0.0565(10) Uani 0.242(2) 1 d D . P A 2
N2A N 0.232(2) 0.9182(8) 0.4493(15) 0.0792(12) Uani 0.242(2) 1 d D . P A 2
C1A C 0.259(2) 0.4244(6) 0.5247(13) 0.0319(9) Uani 0.242(2) 1 d D . P A 2
C6A C 0.327(2) 0.5078(10) 0.6353(9) 0.0389(9) Uani 0.242(2) 1 d G . P A 2
H6A H 0.377973 0.478174 0.726568 0.047 Uiso 0.242(2) 1 calc R . P A 2
C5A C 0.318(2) 0.6355(9) 0.6095(10) 0.0436(9) Uani 0.242(2) 1 d G . P A 2
H5A H 0.363710 0.691354 0.683518 0.052 Uiso 0.242(2) 1 calc R . P A 2
C4A C 0.242(2) 0.6798(6) 0.4731(12) 0.0390(9) Uani 0.242(2) 1 d DG . P A 2
C3A C 0.174(2) 0.5964(10) 0.3625(9) 0.0440(9) Uani 0.242(2) 1 d G . P A 2
H3A H 0.123025 0.626060 0.271277 0.053 Uiso 0.242(2) 1 calc R . P A 2
C2A C 0.183(2) 0.4687(9) 0.3883(10) 0.0408(9) Uani 0.242(2) 1 d G . P A 2
H2A H 0.137287 0.412879 0.314324 0.049 Uiso 0.242(2) 1 calc R . P A 2
C7A C 0.2567(14) 0.2819(7) 0.5381(8) 0.0379(7) Uani 0.242(2) 1 d D . P A 2
O0 O 0.2385(13) 0.2075(7) 0.4357(7) 0.0593(8) Uani 0.242(2) 1 d D . P A 2
N1A N 0.2685(13) 0.2448(7) 0.6618(8) 0.0511(8) Uani 0.242(2) 1 d D . P A 2
H1AA H 0.264143 0.166331 0.678888 0.061 Uiso 0.242(2) 1 calc R . P A 2
H1AB H 0.280744 0.298280 0.728209 0.061 Uiso 0.242(2) 1 calc R . 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
O1 C7 1.233(4) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C1 C7 1.501(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C4 C8 1.430(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C7 1.316(4) . ?
N2 C8 1.145(4) . ?
C8A N2A 1.158(8) . ?
C8A C4A 1.405(8) . ?
C1A C6A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A C7A 1.532(8) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C4A 1.3900 . ?
C4A C3A 1.3900 . ?
C3A H3A 0.9300 . ?
C3A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C7A O0 1.271(8) . ?
C7A N1A 1.276(8) . ?
N1A H1AA 0.8600 . ?
N1A H1AB 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0 . . ?
C6 C1 C7 121.65(16) . . ?
C2 C1 C7 118.30(16) . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C8 121.95(19) . . ?
C3 C4 C8 118.04(19) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
O1 C7 C1 120.1(2) . . ?
O1 C7 N1 121.3(3) . . ?
N1 C7 C1 118.6(3) . . ?
N2 C8 C4 179.6(4) . . ?
N2A C8A C4A 178.0(16) . . ?
C6A C1A C2A 120.0 . . ?
C6A C1A C7A 125.5(8) . . ?
C2A C1A C7A 114.4(8) . . ?
C1A C6A H6A 120.0 . . ?
C1A C6A C5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C4A C8A 114.1(10) . . ?
C5A C4A C3A 120.0 . . ?
C3A C4A C8A 125.9(10) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
O0 C7A C1A 123.8(8) . . ?
O0 C7A N1A 122.9(8) . . ?
N1A C7A C1A 113.3(7) . . ?
C7A N1A H1AA 120.0 . . ?
C7A N1A H1AB 120.0 . . ?
H1AA N1A H1AB 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
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C7 O1 -159.9(3) . . . . ?
C6 C1 C7 N1 19.6(4) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C5 C4 C8 -178.8(4) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C7 O1 17.5(4) . . . . ?
C2 C1 C7 N1 -163.0(3) . . . . ?
C7 C1 C6 C5 177.4(3) . . . . ?
C7 C1 C2 C3 -177.5(3) . . . . ?
C8 C4 C3 C2 178.8(4) . . . . ?
C8A C4A C3A C2A -178.7(14) . . . . ?
C1A C6A C5A C4A 0.0 . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C6A C1A C7A O0 -162.7(10) . . . . ?
C6A C1A C7A N1A 19.5(14) . . . . ?
C6A C5A C4A C8A 178.8(13) . . . . ?
C6A C5A C4A C3A 0.0 . . . . ?
C5A C4A C3A C2A 0.0 . . . . ?
C4A C3A C2A C1A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C1A C7A O0 18.2(14) . . . . ?
C2A C1A C7A N1A -159.6(9) . . . . ?
C7A C1A C6A C5A -179.0(12) . . . . ?
C7A C1A C2A C3A 179.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.551
