# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_yst7102
_database_code_depnum_ccdc_archive 'CCDC 2161537'
loop_
_audit_author_name
_audit_author_address
'Sitian Yuan'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   43.7224(17)
_cell_length_b                   14.1940(6)
_cell_length_c                   8.7864(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5452.8(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9950
_cell_measurement_theta_min      4.2450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8647
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.198
_diffrn_reflns_theta_min         3.423
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0706
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  12.00   0.75   45.54    --  -15.92 -19.00 -90.00  132
  2  ω    -83.00  10.00   0.75   45.54    --  -15.92 -77.00  30.00  124
  3  ω    -89.00 -35.00   0.75   45.54    --  -15.92 178.00 -60.00   72
  4  ω      0.00  41.25   0.75   45.54    --   16.70  57.00-150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146011000
_diffrn_orient_matrix_UB_12      0.0211182000
_diffrn_orient_matrix_UB_13      -0.0083385000
_diffrn_orient_matrix_UB_21      0.0070611000
_diffrn_orient_matrix_UB_22      -0.0437534000
_diffrn_orient_matrix_UB_23      0.0171063000
_diffrn_orient_matrix_UB_31      -0.0000113000
_diffrn_orient_matrix_UB_32      -0.0118466000
_diffrn_orient_matrix_UB_33      -0.0784213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2788
_reflns_number_total             2909
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      0.929
_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)+(0.0361P)²+6.7467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0829
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C12(H12), C11(H11), C4(H4), C6(H6), C13(H13), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_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 0.54047(4) 0.98991(11) 0.58888(18) 0.0511(4) Uani 1 1 d . . . . .
N2 N 0.56059(4) 0.82726(12) 0.4949(2) 0.0346(3) Uani 1 1 d . . . . .
N1 N 0.60250(4) 0.80577(12) 0.2463(2) 0.0361(4) Uani 1 1 d . . . . .
C2 C 0.57694(5) 0.82844(13) 0.1517(2) 0.0360(4) Uani 1 1 d . . . . .
C9 C 0.57417(4) 0.73950(14) 0.4602(2) 0.0340(4) Uani 1 1 d . . . . .
O2 O 0.53629(5) 1.04245(12) 0.3516(2) 0.0633(5) Uani 1 1 d . . . . .
C15 C 0.54118(4) 0.98017(14) 0.4388(2) 0.0349(4) Uani 1 1 d . . . . .
C3 C 0.57730(6) 0.81942(17) -0.0054(3) 0.0528(6) Uani 1 1 d . . . . .
H3 H 0.594877 0.798239 -0.054174 0.063 Uiso 1 1 calc R . . . .
C10 C 0.56782(5) 0.66458(16) 0.5574(3) 0.0453(5) Uani 1 1 d . . . . .
H10 H 0.553676 0.672468 0.635392 0.054 Uiso 1 1 calc R . . . .
C12 C 0.60427(6) 0.56862(17) 0.4281(3) 0.0547(6) Uani 1 1 d . . . . .
H12 H 0.614407 0.511385 0.417507 0.066 Uiso 1 1 calc R . . . .
C11 C 0.58217(6) 0.57887(17) 0.5396(3) 0.0538(6) Uani 1 1 d . . . . .
H11 H 0.577050 0.528337 0.601922 0.065 Uiso 1 1 calc R . . . .
C14 C 0.59610(4) 0.72834(13) 0.3454(2) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.55156(8) 0.8419(2) -0.0900(3) 0.0703(9) Uani 1 1 d . . . . .
H4 H 0.552051 0.836987 -0.195500 0.084 Uiso 1 1 calc R . . . .
C8 C 0.55134(4) 0.88238(13) 0.3900(2) 0.0317(4) Uani 1 1 d . . . . .
C6 C 0.52482(6) 0.88334(19) 0.1370(3) 0.0544(6) Uani 1 1 d . . . . .
H6 H 0.507103 0.904967 0.183950 0.065 Uiso 1 1 calc R . . . .
C16 C 0.53446(6) 1.0841(2) 0.6452(3) 0.0601(7) Uani 1 1 d . . . . .
H16A H 0.547302 1.128317 0.592853 0.090 Uiso 1 1 calc GR . . . .
H16B H 0.538699 1.086530 0.752365 0.090 Uiso 1 1 calc GR . . . .
H16C H 0.513387 1.099758 0.627818 0.090 Uiso 1 1 calc GR . . . .
C7 C 0.55063(4) 0.86339(14) 0.2241(2) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.63263(6) 0.80532(18) 0.1739(3) 0.0541(6) Uani 1 1 d . . . . .
H1A H 0.633613 0.754959 0.101091 0.081 Uiso 1 1 calc GR . . . .
H1B H 0.648129 0.796382 0.249882 0.081 Uiso 1 1 calc GR . . . .
H1C H 0.635916 0.864337 0.123039 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.61139(5) 0.64227(15) 0.3329(3) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.626520 0.634740 0.259561 0.054 Uiso 1 1 calc R . . . .
C5 C 0.52545(8) 0.8711(2) -0.0187(3) 0.0747(10) Uani 1 1 d . . . . .
H5 H 0.507947 0.882927 -0.075689 0.090 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.326(3) . ?
O1 C16 1.449(3) . ?
N2 C9 1.413(3) . ?
N2 C8 1.274(3) . ?
N1 C2 1.429(3) . ?
N1 C14 1.430(3) . ?
N1 C1 1.463(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.405(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.401(3) . ?
O2 C15 1.190(3) . ?
C15 C8 1.519(3) . ?
C3 C4 1.386(4) . ?
C10 C11 1.378(3) . ?
C12 C11 1.383(4) . ?
C12 C13 1.374(3) . ?
C14 C13 1.397(3) . ?
C4 C5 1.367(5) . ?
C8 C7 1.483(3) . ?
C6 C7 1.393(3) . ?
C6 C5 1.379(4) . ?

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
C15 O1 C16 116.1(2) . . ?
C8 N2 C9 121.27(17) . . ?
C2 N1 C14 111.97(15) . . ?
C2 N1 C1 116.87(18) . . ?
C14 N1 C1 115.97(17) . . ?
C3 C2 N1 123.3(2) . . ?
C3 C2 C7 119.5(2) . . ?
C7 C2 N1 117.15(18) . . ?
C10 C9 N2 117.25(18) . . ?
C10 C9 C14 119.46(18) . . ?
C14 C9 N2 122.84(17) . . ?
O1 C15 C8 112.50(17) . . ?
O2 C15 O1 124.0(2) . . ?
O2 C15 C8 123.35(18) . . ?
C4 C3 C2 120.2(2) . . ?
C11 C10 C9 120.9(2) . . ?
C13 C12 C11 120.6(2) . . ?
C10 C11 C12 119.4(2) . . ?
C9 C14 N1 119.05(16) . . ?
C13 C14 N1 122.06(18) . . ?
C13 C14 C9 118.89(18) . . ?
C5 C4 C3 120.1(2) . . ?
N2 C8 C15 116.74(17) . . ?
N2 C8 C7 127.26(18) . . ?
C7 C8 C15 115.94(16) . . ?
C5 C6 C7 120.2(3) . . ?
C2 C7 C8 119.49(18) . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 121.36(19) . . ?
C12 C13 C14 120.6(2) . . ?
C4 C5 C6 120.6(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_yst9501
_database_code_depnum_ccdc_archive 'CCDC 2161539'
loop_
_audit_author_name
_audit_author_address
'Sitian Yuan'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N3 O'
_chemical_formula_sum            'C17 H17 N3 O'
_chemical_formula_weight         279.33
_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                   8.4266(7)
_cell_length_b                   13.3424(11)
_cell_length_c                   13.1891(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.252(9)
_cell_angle_gamma                90
_cell_volume                     1476.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1230
_cell_measurement_theta_min      4.0460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.278
_diffrn_reflns_theta_min         3.365
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -35.00   1.00    6.20    --  -15.92-178.00  60.00   53
  2  ω      0.00  84.00   1.00    6.20    --   16.85  57.00   0.00   84
  3  ω    -55.00  46.00   1.00    6.20    --   16.85 -19.00-150.00  101
  4  ω    -35.00  53.00   1.00    6.20    --  -15.92  37.00  60.00   88
  5  ω      0.00  78.00   1.00    6.20    --   16.85  57.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049103000
_diffrn_orient_matrix_UB_12      0.0194037000
_diffrn_orient_matrix_UB_13      0.0502772000
_diffrn_orient_matrix_UB_21      0.0835878000
_diffrn_orient_matrix_UB_22      -0.0081809000
_diffrn_orient_matrix_UB_23      0.0048239000
_diffrn_orient_matrix_UB_31      0.0121921000
_diffrn_orient_matrix_UB_32      0.0487600000
_diffrn_orient_matrix_UB_33      -0.0191015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2796
_reflns_number_total             3538
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.033
_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)+(0.0595P)²+0.3356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1309
_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:
 C6(H6), C13(H13), C4(H4), C5(H5), C10(H10), C3(H3), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_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
N2 N 0.04326(13) 0.41953(9) 0.65254(9) 0.0390(3) Uani 1 1 d . . . . .
O1 O -0.10953(14) 0.53199(9) 0.82300(12) 0.0709(4) Uani 1 1 d . . . . .
N1 N 0.19445(14) 0.22901(8) 0.69178(9) 0.0397(3) Uani 1 1 d . . . . .
N3 N -0.24578(14) 0.39016(10) 0.78236(10) 0.0495(3) Uani 1 1 d . . . . .
C2 C 0.22697(15) 0.26547(10) 0.79281(10) 0.0355(3) Uani 1 1 d . . . . .
C14 C 0.24852(15) 0.29420(11) 0.61668(10) 0.0366(3) Uani 1 1 d . . . . .
C9 C 0.17543(16) 0.38798(11) 0.60140(10) 0.0363(3) Uani 1 1 d . . . . .
C6 C 0.17197(18) 0.38679(11) 0.92101(11) 0.0433(3) Uani 1 1 d . . . . .
H6 H 0.118926 0.443937 0.940057 0.052 Uiso 1 1 calc R . . . .
C8 C 0.03243(15) 0.40260(10) 0.74665(10) 0.0339(3) Uani 1 1 d . . . . .
C7 C 0.14785(15) 0.35214(10) 0.82072(10) 0.0337(3) Uani 1 1 d . . . . .
C15 C -0.11536(17) 0.44723(11) 0.78779(11) 0.0426(3) Uani 1 1 d . . . . .
C13 C 0.36735(19) 0.26647(13) 0.55524(12) 0.0505(4) Uani 1 1 d . . . . .
H13 H 0.416727 0.204401 0.564686 0.061 Uiso 1 1 calc R . . . .
C4 C 0.3506(2) 0.25238(15) 0.96417(13) 0.0585(5) Uani 1 1 d . . . . .
H4 H 0.418529 0.218746 1.012272 0.070 Uiso 1 1 calc R . . . .
C5 C 0.2735(2) 0.33717(13) 0.99188(12) 0.0553(4) Uani 1 1 d . . . . .
H5 H 0.289624 0.361085 1.058252 0.066 Uiso 1 1 calc R . . . .
C10 C 0.2202(2) 0.45002(13) 0.52439(11) 0.0496(4) Uani 1 1 d . . . . .
H10 H 0.169387 0.511331 0.512600 0.059 Uiso 1 1 calc R . . . .
C3 C 0.32868(19) 0.21614(12) 0.86544(12) 0.0484(4) Uani 1 1 d . . . . .
H3 H 0.382112 0.158671 0.847669 0.058 Uiso 1 1 calc R . . . .
C12 C 0.4124(2) 0.33003(16) 0.48069(13) 0.0623(5) Uani 1 1 d . . . . .
H12 H 0.492491 0.310815 0.440693 0.075 Uiso 1 1 calc R . . . .
C11 C 0.3397(2) 0.42160(16) 0.46504(13) 0.0619(5) Uani 1 1 d . . . . .
H11 H 0.370703 0.464328 0.414751 0.074 Uiso 1 1 calc R . . . .
C16 C -0.2545(2) 0.28919(13) 0.74187(15) 0.0609(5) Uani 1 1 d . . . . .
H16A H -0.324310 0.288073 0.680152 0.091 Uiso 1 1 calc GR . . . .
H16B H -0.294802 0.244914 0.790824 0.091 Uiso 1 1 calc GR . . . .
H16C H -0.149999 0.267659 0.727799 0.091 Uiso 1 1 calc GR . . . .
C1 C 0.2202(2) 0.12187(12) 0.67689(15) 0.0603(5) Uani 1 1 d . . . . .
H1A H 0.332364 0.107805 0.684737 0.090 Uiso 1 1 calc GR . . . .
H1B H 0.177111 0.102917 0.609726 0.090 Uiso 1 1 calc GR . . . .
H1C H 0.167969 0.084518 0.726442 0.090 Uiso 1 1 calc GR . . . .
C17 C -0.3926(2) 0.43137(18) 0.8157(2) 0.0863(7) Uani 1 1 d . . . . .
H17A H -0.411996 0.402476 0.880111 0.129 Uiso 1 1 calc GR . . . .
H17B H -0.479965 0.416004 0.766269 0.129 Uiso 1 1 calc GR . . . .
H17C H -0.382525 0.502753 0.822795 0.129 Uiso 1 1 calc GR . . . .


_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
N2 C9 1.4178(17) . ?
N2 C8 1.2731(17) . ?
O1 C15 1.2218(18) . ?
N1 C2 1.4213(18) . ?
N1 C14 1.4240(18) . ?
N1 C1 1.4619(19) . ?
N3 C15 1.3335(19) . ?
N3 C16 1.449(2) . ?
N3 C17 1.458(2) . ?
C2 C7 1.4008(19) . ?
C2 C3 1.391(2) . ?
C14 C9 1.401(2) . ?
C14 C13 1.3946(19) . ?
C9 C10 1.389(2) . ?
C6 C7 1.3983(19) . ?
C6 C5 1.377(2) . ?
C8 C7 1.4763(18) . ?
C8 C15 1.5243(18) . ?
C13 C12 1.378(2) . ?
C4 C5 1.371(3) . ?
C4 C3 1.386(2) . ?
C10 C11 1.384(2) . ?
C12 C11 1.374(3) . ?

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
C8 N2 C9 122.73(12) . . ?
C2 N1 C14 113.36(11) . . ?
C2 N1 C1 116.26(13) . . ?
C14 N1 C1 116.30(12) . . ?
C15 N3 C16 124.36(13) . . ?
C15 N3 C17 119.10(15) . . ?
C16 N3 C17 116.51(14) . . ?
C7 C2 N1 118.25(12) . . ?
C3 C2 N1 122.50(13) . . ?
C3 C2 C7 119.19(13) . . ?
C9 C14 N1 118.76(12) . . ?
C13 C14 N1 122.32(13) . . ?
C13 C14 C9 118.88(14) . . ?
C14 C9 N2 123.43(12) . . ?
C10 C9 N2 116.67(13) . . ?
C10 C9 C14 119.47(13) . . ?
C5 C6 C7 120.70(15) . . ?
N2 C8 C7 128.64(12) . . ?
N2 C8 C15 114.30(12) . . ?
C7 C8 C15 116.92(11) . . ?
C2 C7 C8 120.20(12) . . ?
C6 C7 C2 119.34(13) . . ?
C6 C7 C8 120.34(12) . . ?
O1 C15 N3 123.58(14) . . ?
O1 C15 C8 119.42(13) . . ?
N3 C15 C8 117.00(12) . . ?
C12 C13 C14 120.71(16) . . ?
C5 C4 C3 120.85(15) . . ?
C4 C5 C6 119.73(15) . . ?
C11 C10 C9 120.73(16) . . ?
C4 C3 C2 120.19(15) . . ?
C11 C12 C13 120.43(15) . . ?
C12 C11 C10 119.75(16) . . ?


_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 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.534
