# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx8663
_database_code_depnum_ccdc_archive 'CCDC 2223180'
loop_
_audit_author_name
_audit_author_address
'Dongfeng Zhang'
;Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences
China
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2020-09-11
_audit_creation_method           
;
Olex2 1.2
(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         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9663(2)
_cell_length_b                   9.2196(3)
_cell_length_c                   10.1384(3)
_cell_angle_alpha                109.529(3)
_cell_angle_beta                 106.432(2)
_cell_angle_gamma                96.016(2)
_cell_volume                     738.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10071
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      31.1820
_cell_measurement_theta_min      2.2190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13059
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.331
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  55.00   0.50    3.00    --    5.00  45.00  60.00   56
  2  ω    -30.00  -4.00   0.50    3.00    --    5.00  45.00  60.00   52
  3  ω    -79.00  93.00   0.50    3.00    --    5.00  45.00 150.00  344
  4  ω     -3.00  56.00   0.50    3.00    --   -8.00  45.00   0.00  118
  5  ω    -82.00 -32.00   0.50    3.00    --   -8.00  45.00   0.00  100
  6  ω    -97.00  80.00   0.50    3.00    --   -8.00  45.00  90.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088026000
_diffrn_orient_matrix_UB_12      -0.0438819000
_diffrn_orient_matrix_UB_13      -0.0685875000
_diffrn_orient_matrix_UB_21      -0.0074278000
_diffrn_orient_matrix_UB_22      0.0650896000
_diffrn_orient_matrix_UB_23      -0.0219191000
_diffrn_orient_matrix_UB_31      0.0837699000
_diffrn_orient_matrix_UB_32      0.0290139000
_diffrn_orient_matrix_UB_33      0.0322803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3692
_reflns_number_total             3958
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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         0.319
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.049
_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)+(0.0643P)²+0.2238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1161
_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 Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.53510(10) 0.39569(9) 0.09942(9) 0.03137(19) Uani 1 1 d . . . . .
O2 O 0.80859(10) 0.79732(11) 0.54339(9) 0.0354(2) Uani 1 1 d . . . . .
N1 N 0.69820(10) 0.57845(11) 0.32626(10) 0.02411(18) Uani 1 1 d . . . . .
N2 N 0.30048(10) 0.56228(9) 0.39071(9) 0.02253(18) Uani 1 1 d . . . . .
C1 C 0.55681(11) 0.51341(11) 0.20717(11) 0.02144(19) Uani 1 1 d . . . . .
C2 C 0.43831(11) 0.61576(11) 0.23934(10) 0.01875(18) Uani 1 1 d . . . . .
H2 H 0.404255 0.663711 0.166048 0.023 Uiso 1 1 calc R . . . .
C3 C 0.52582(11) 0.73883(11) 0.39622(10) 0.02038(19) Uani 1 1 d . . . . .
H3 H 0.520023 0.846485 0.402860 0.024 Uiso 1 1 calc R . . . .
C4 C 0.69486(12) 0.71640(12) 0.43511(11) 0.0242(2) Uani 1 1 d . . . . .
C5 C 0.29804(11) 0.52482(10) 0.25660(10) 0.01927(18) Uani 1 1 d . . . . .
C6 C 0.44185(12) 0.68648(11) 0.49442(10) 0.02072(19) Uani 1 1 d . . . . .
H6 H 0.514285 0.638988 0.551087 0.025 Uiso 1 1 calc R . . . .
C7 C 0.83433(13) 0.50475(16) 0.33915(14) 0.0334(3) Uani 1 1 d . . . . .
H7A H 0.820962 0.427014 0.380974 0.050 Uiso 1 1 calc GR . . . .
H7B H 0.929921 0.583576 0.402607 0.050 Uiso 1 1 calc GR . . . .
H7C H 0.842031 0.454951 0.242404 0.050 Uiso 1 1 calc GR . . . .
C8 C 0.17102(11) 0.40129(11) 0.12923(10) 0.01978(19) Uani 1 1 d . . . . .
C9 C 0.14970(12) 0.39018(12) -0.01561(11) 0.0249(2) Uani 1 1 d . . . . .
H9 H 0.217659 0.459702 -0.032764 0.030 Uiso 1 1 calc R . . . .
C10 C 0.02723(13) 0.27557(14) -0.13469(12) 0.0302(2) Uani 1 1 d . . . . .
H10 H 0.013263 0.269351 -0.231028 0.036 Uiso 1 1 calc R . . . .
C11 C -0.07372(14) 0.17099(14) -0.11082(13) 0.0339(3) Uani 1 1 d . . . . .
H11 H -0.155224 0.094259 -0.190809 0.041 Uiso 1 1 calc R . . . .
C12 C -0.05311(14) 0.18081(14) 0.03274(14) 0.0331(2) Uani 1 1 d . . . . .
H12 H -0.121214 0.110509 0.048942 0.040 Uiso 1 1 calc R . . . .
C13 C 0.06853(12) 0.29487(12) 0.15273(12) 0.0259(2) Uani 1 1 d . . . . .
H13 H 0.081825 0.300473 0.248797 0.031 Uiso 1 1 calc R . . . .
C14 C 0.40150(12) 0.81952(11) 0.60389(10) 0.02014(19) Uani 1 1 d . . . . .
C15 C 0.51787(12) 0.91031(12) 0.74111(11) 0.0240(2) Uani 1 1 d . . . . .
H15 H 0.618426 0.887552 0.764288 0.029 Uiso 1 1 calc R . . . .
C16 C 0.48472(13) 1.03447(12) 0.84346(11) 0.0267(2) Uani 1 1 d . . . . .
H16 H 0.563776 1.096307 0.933774 0.032 Uiso 1 1 calc R . . . .
C17 C 0.33401(14) 1.06624(12) 0.81110(12) 0.0286(2) Uani 1 1 d . . . . .
H17 H 0.311234 1.148370 0.880229 0.034 Uiso 1 1 calc R . . . .
C18 C 0.21714(13) 0.97549(13) 0.67554(13) 0.0315(2) Uani 1 1 d . . . . .
H18 H 0.115597 0.996194 0.654047 0.038 Uiso 1 1 calc R . . . .
C19 C 0.25141(13) 0.85356(12) 0.57161(12) 0.0273(2) Uani 1 1 d . . . . .
H19 H 0.173278 0.794448 0.479910 0.033 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 C1 1.2050(12) . ?
O2 C4 1.2088(13) . ?
N1 C1 1.3839(13) . ?
N1 C4 1.3873(14) . ?
N1 C7 1.4531(13) . ?
N2 C5 1.2791(12) . ?
N2 C6 1.4698(12) . ?
C1 C2 1.5251(13) . ?
C2 C3 1.5276(12) . ?
C2 C5 1.5222(13) . ?
C3 C4 1.5092(14) . ?
C3 C6 1.5685(13) . ?
C5 C8 1.4746(13) . ?
C6 C14 1.5091(13) . ?
C8 C9 1.3929(14) . ?
C8 C13 1.3982(14) . ?
C9 C10 1.3906(14) . ?
C10 C11 1.3800(17) . ?
C11 C12 1.3846(18) . ?
C12 C13 1.3889(15) . ?
C14 C15 1.3936(13) . ?
C14 C19 1.3872(14) . ?
C15 C16 1.3882(14) . ?
C16 C17 1.3842(16) . ?
C17 C18 1.3855(16) . ?
C18 C19 1.3900(15) . ?

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
C1 N1 C4 113.64(8) . . ?
C1 N1 C7 123.01(9) . . ?
C4 N1 C7 123.28(9) . . ?
C5 N2 C6 110.83(8) . . ?
O1 C1 N1 124.51(9) . . ?
O1 C1 C2 127.66(9) . . ?
N1 C1 C2 107.83(8) . . ?
C1 C2 C3 104.54(7) . . ?
C5 C2 C1 111.16(7) . . ?
C5 C2 C3 103.30(7) . . ?
C2 C3 C6 103.79(7) . . ?
C4 C3 C2 105.33(8) . . ?
C4 C3 C6 109.72(8) . . ?
O2 C4 N1 124.31(10) . . ?
O2 C4 C3 127.91(10) . . ?
N1 C4 C3 107.72(8) . . ?
N2 C5 C2 114.64(8) . . ?
N2 C5 C8 122.64(9) . . ?
C8 C5 C2 122.70(8) . . ?
N2 C6 C3 106.38(7) . . ?
N2 C6 C14 112.45(8) . . ?
C14 C6 C3 114.27(7) . . ?
C9 C8 C5 120.72(9) . . ?
C9 C8 C13 119.05(9) . . ?
C13 C8 C5 120.22(9) . . ?
C10 C9 C8 120.27(10) . . ?
C11 C10 C9 120.43(10) . . ?
C10 C11 C12 119.70(10) . . ?
C11 C12 C13 120.48(10) . . ?
C12 C13 C8 120.06(10) . . ?
C15 C14 C6 119.16(9) . . ?
C19 C14 C6 121.71(9) . . ?
C19 C14 C15 119.13(9) . . ?
C16 C15 C14 120.45(10) . . ?
C17 C16 C15 120.00(9) . . ?
C16 C17 C18 119.89(10) . . ?
C17 C18 C19 120.11(10) . . ?
C14 C19 C18 120.38(9) . . ?

_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.830
####################################################################### 
# 
# 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_mx10528
_database_code_depnum_ccdc_archive 'CCDC 2223184'
loop_
_audit_author_name
_audit_author_address
'Dongfeng Zhang'
;Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences
China
;
_audit_update_record             
;
2022-11-30 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.6247(4)
_cell_length_b                   7.6878(2)
_cell_length_c                   22.1932(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3007.07(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12395
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.6870
_cell_measurement_theta_min      1.8020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.739
_diffrn_reflns_theta_min         1.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  46.00   0.50    3.00    --  -14.80  45.00  -4.87  236
  2  ω     21.00  46.00   0.50    3.00    --  -14.80  45.00  -4.87   50
  3  ω    -18.00  74.00   0.50    3.00    --  -14.80  45.00  60.00  184
  4  ω   -104.00   1.00   0.50    3.00    --  -14.80  45.00  30.00  210
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350738000
_diffrn_orient_matrix_UB_12      0.0448104000
_diffrn_orient_matrix_UB_13      0.0026110000
_diffrn_orient_matrix_UB_21      0.0170251000
_diffrn_orient_matrix_UB_22      0.0604236000
_diffrn_orient_matrix_UB_23      0.0200152000
_diffrn_orient_matrix_UB_31      0.0099600000
_diffrn_orient_matrix_UB_32      0.0532964000
_diffrn_orient_matrix_UB_33      -0.0248168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3683
_reflns_number_total             4173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_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     209
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.067
_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)+(0.0665P)²+0.6758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1147
_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 Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.48800(4) 0.30364(12) 0.75383(4) 0.03217(19) Uani 1 1 d . . . . .
O2 O 0.56731(5) 0.15865(11) 0.56582(3) 0.03090(18) Uani 1 1 d . . . . .
N1 N 0.51206(5) 0.23499(11) 0.65537(4) 0.02174(18) Uani 1 1 d . . . . .
N2 N 0.71276(5) 0.37752(11) 0.71644(4) 0.02200(17) Uani 1 1 d . . . . .
C1 C 0.53013(5) 0.24813(13) 0.71561(4) 0.02123(19) Uani 1 1 d . . . . .
C2 C 0.61085(5) 0.18006(12) 0.72341(4) 0.01960(18) Uani 1 1 d . . . . .
H2 H 0.611302 0.067119 0.743879 0.024 Uiso 1 1 calc R U . . .
C3 C 0.66573(5) 0.30648(12) 0.75267(4) 0.01912(18) Uani 1 1 d . . . . .
C4 C 0.69756(5) 0.32316(12) 0.65431(4) 0.02044(19) Uani 1 1 d . . . . .
H4 H 0.744982 0.283572 0.635772 0.025 Uiso 1 1 calc R U . . .
C5 C 0.64121(5) 0.16525(12) 0.65915(4) 0.02061(19) Uani 1 1 d . . . . .
H5 H 0.667281 0.054219 0.652658 0.025 Uiso 1 1 calc R U . . .
C6 C 0.57220(6) 0.18193(12) 0.61942(4) 0.02166(19) Uani 1 1 d . . . . .
C7 C 0.43858(6) 0.28098(17) 0.63092(5) 0.0335(2) Uani 1 1 d . . . . .
H7A H 0.402977 0.295709 0.663250 0.050 Uiso 1 1 calc R U . . .
H7B H 0.421336 0.190071 0.604615 0.050 Uiso 1 1 calc R U . . .
H7C H 0.442726 0.387657 0.608672 0.050 Uiso 1 1 calc R U . . .
C8 C 0.66614(5) 0.34384(12) 0.81788(4) 0.02007(19) Uani 1 1 d . . . . .
C9 C 0.61316(6) 0.26830(13) 0.85647(4) 0.0238(2) Uani 1 1 d . . . . .
H9 H 0.576433 0.193800 0.841007 0.029 Uiso 1 1 calc R U . . .
C10 C 0.61480(6) 0.30350(15) 0.91797(5) 0.0268(2) Uani 1 1 d . . . . .
H10 H 0.579458 0.252018 0.943473 0.032 Uiso 1 1 calc R U . . .
C11 C 0.66897(6) 0.41501(14) 0.94113(5) 0.0270(2) Uani 1 1 d . . . . .
H11 H 0.670201 0.438485 0.982231 0.032 Uiso 1 1 calc R U . . .
C12 C 0.72159(6) 0.49194(14) 0.90288(5) 0.0277(2) Uani 1 1 d . . . . .
H12 H 0.757815 0.567560 0.918439 0.033 Uiso 1 1 calc R U . . .
C13 C 0.72037(6) 0.45667(13) 0.84179(4) 0.0248(2) Uani 1 1 d . . . . .
H13 H 0.755886 0.508414 0.816501 0.030 Uiso 1 1 calc R U . . .
C14 C 0.66633(5) 0.47480(12) 0.61837(4) 0.01910(18) Uani 1 1 d . . . . .
C15 C 0.61809(5) 0.59623(12) 0.64483(4) 0.02127(19) Uani 1 1 d . . . . .
H15 H 0.607427 0.589225 0.685793 0.026 Uiso 1 1 calc R U . . .
C16 C 0.58589(6) 0.72741(13) 0.61050(5) 0.0246(2) Uani 1 1 d . . . . .
H16 H 0.553583 0.807622 0.628544 0.029 Uiso 1 1 calc R U . . .
C17 C 0.60153(6) 0.73988(14) 0.54937(5) 0.0284(2) Uani 1 1 d . . . . .
H17 H 0.579210 0.826784 0.526232 0.034 Uiso 1 1 calc R U . . .
C18 C 0.65076(6) 0.62144(15) 0.52320(5) 0.0305(2) Uani 1 1 d . . . . .
H18 H 0.662349 0.630367 0.482438 0.037 Uiso 1 1 calc R U . . .
C19 C 0.68287(6) 0.48969(14) 0.55741(4) 0.0251(2) Uani 1 1 d . . . . .
H19 H 0.715740 0.410656 0.539379 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2055(12) . ?
O2 C6 1.2059(12) . ?
N1 C1 1.3781(12) . ?
N1 C6 1.3880(13) . ?
N1 C7 1.4479(13) . ?
N2 C3 1.2775(12) . ?
N2 C4 1.4655(12) . ?
C1 C2 1.5257(13) . ?
C2 H2 0.9800 . ?
C2 C3 1.5171(13) . ?
C2 C5 1.5274(13) . ?
C3 C8 1.4755(12) . ?
C4 H4 0.9800 . ?
C4 C5 1.5721(13) . ?
C4 C14 1.5160(13) . ?
C5 H5 0.9800 . ?
C5 C6 1.5077(13) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.3937(13) . ?
C8 C13 1.3957(13) . ?
C9 H9 0.9300 . ?
C9 C10 1.3917(14) . ?
C10 H10 0.9300 . ?
C10 C11 1.3823(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.3895(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.3827(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.3924(12) . ?
C14 C19 1.3888(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.3855(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.3876(14) . ?
C17 H17 0.9300 . ?
C17 C18 1.3854(15) . ?
C18 H18 0.9300 . ?
C18 C19 1.3865(15) . ?
C19 H19 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
C1 N1 C6 113.75(8) . . ?
C1 N1 C7 123.54(9) . . ?
C6 N1 C7 122.64(8) . . ?
C3 N2 C4 110.58(8) . . ?
O1 C1 N1 124.49(9) . . ?
O1 C1 C2 128.03(9) . . ?
N1 C1 C2 107.48(8) . . ?
C1 C2 H2 111.3 . . ?
C1 C2 C5 104.26(7) . . ?
C3 C2 C1 115.04(8) . . ?
C3 C2 H2 111.3 . . ?
C3 C2 C5 102.95(7) . . ?
C5 C2 H2 111.3 . . ?
N2 C3 C2 114.72(8) . . ?
N2 C3 C8 122.07(8) . . ?
C8 C3 C2 123.20(8) . . ?
N2 C4 H4 109.1 . . ?
N2 C4 C5 105.75(7) . . ?
N2 C4 C14 110.00(8) . . ?
C5 C4 H4 109.1 . . ?
C14 C4 H4 109.1 . . ?
C14 C4 C5 113.60(7) . . ?
C2 C5 C4 103.15(7) . . ?
C2 C5 H5 111.5 . . ?
C4 C5 H5 111.5 . . ?
C6 C5 C2 104.90(7) . . ?
C6 C5 C4 113.83(8) . . ?
C6 C5 H5 111.5 . . ?
O2 C6 N1 123.78(9) . . ?
O2 C6 C5 128.46(9) . . ?
N1 C6 C5 107.75(8) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 121.23(9) . . ?
C9 C8 C13 118.96(9) . . ?
C13 C8 C3 119.82(8) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.52(9) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.97(10) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.85(9) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.35(9) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.35(9) . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C4 121.03(8) . . ?
C19 C14 C4 119.98(8) . . ?
C19 C14 C15 118.92(9) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.42(9) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.43(9) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.27(9) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.41(10) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.53(9) . . ?
C18 C19 H19 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -56.30(14) . . . . ?
O1 C1 C2 C5 -168.26(10) . . . . ?
N1 C1 C2 C3 123.93(8) . . . . ?
N1 C1 C2 C5 11.98(10) . . . . ?
N2 C3 C8 C9 178.40(9) . . . . ?
N2 C3 C8 C13 -1.63(14) . . . . ?
N2 C4 C5 C2 16.75(9) . . . . ?
N2 C4 C5 C6 129.82(8) . . . . ?
N2 C4 C14 C15 -35.87(11) . . . . ?
N2 C4 C14 C19 147.16(9) . . . . ?
C1 N1 C6 O2 178.13(9) . . . . ?
C1 N1 C6 C5 -3.24(11) . . . . ?
C1 C2 C3 N2 -104.79(10) . . . . ?
C1 C2 C3 C8 76.05(11) . . . . ?
C1 C2 C5 C4 106.02(8) . . . . ?
C1 C2 C5 C6 -13.42(9) . . . . ?
C2 C3 C8 C9 -2.49(14) . . . . ?
C2 C3 C8 C13 177.48(9) . . . . ?
C2 C5 C6 O2 -170.80(10) . . . . ?
C2 C5 C6 N1 10.66(10) . . . . ?
C3 N2 C4 C5 -12.83(10) . . . . ?
C3 N2 C4 C14 110.22(9) . . . . ?
C3 C2 C5 C4 -14.42(9) . . . . ?
C3 C2 C5 C6 -133.85(7) . . . . ?
C3 C8 C9 C10 179.34(9) . . . . ?
C3 C8 C13 C12 -179.64(9) . . . . ?
C4 N2 C3 C2 3.25(11) . . . . ?
C4 N2 C3 C8 -177.58(8) . . . . ?
C4 C5 C6 O2 77.19(13) . . . . ?
C4 C5 C6 N1 -101.36(9) . . . . ?
C4 C14 C15 C16 -175.62(9) . . . . ?
C4 C14 C19 C18 175.87(10) . . . . ?
C5 C2 C3 N2 7.94(10) . . . . ?
C5 C2 C3 C8 -171.22(8) . . . . ?
C5 C4 C14 C15 82.45(10) . . . . ?
C5 C4 C14 C19 -94.53(10) . . . . ?
C6 N1 C1 O1 174.49(10) . . . . ?
C6 N1 C1 C2 -5.73(11) . . . . ?
C7 N1 C1 O1 -2.32(16) . . . . ?
C7 N1 C1 C2 177.46(9) . . . . ?
C7 N1 C6 O2 -5.03(16) . . . . ?
C7 N1 C6 C5 173.60(9) . . . . ?
C8 C9 C10 C11 0.41(16) . . . . ?
C9 C8 C13 C12 0.33(15) . . . . ?
C9 C10 C11 C12 0.12(16) . . . . ?
C10 C11 C12 C13 -0.43(16) . . . . ?
C11 C12 C13 C8 0.20(16) . . . . ?
C13 C8 C9 C10 -0.63(15) . . . . ?
C14 C4 C5 C2 -103.98(8) . . . . ?
C14 C4 C5 C6 9.08(11) . . . . ?
C14 C15 C16 C17 -0.26(15) . . . . ?
C15 C14 C19 C18 -1.17(15) . . . . ?
C15 C16 C17 C18 -1.10(16) . . . . ?
C16 C17 C18 C19 1.31(17) . . . . ?
C17 C18 C19 C14 -0.18(17) . . . . ?
C19 C14 C15 C16 1.39(14) . . . . ?

_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.711
