# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2169489'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   11.5596(3)
_cell_length_b                   10.6483(2)
_cell_length_c                   14.4503(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.178(3)
_cell_angle_gamma                90
_cell_volume                     1647.09(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2950
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68999
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.521
_diffrn_reflns_theta_min         4.204
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  14.00   1.00    1.00    --  -35.62 106.00 -10.00   92
  2  ω      8.00  78.00   1.00    1.00    --   35.62-106.00-109.00   70
  3  ω     37.00 112.00   1.00    2.78    --  107.12-106.00-109.00   75
  4  ω    101.00 177.00   1.00    2.78    --  107.12 106.00 -10.00   76
  5  ω    -65.00  36.00   1.00    1.00    --  -35.62  19.00  60.00  101
  6  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-120.00   51
  7  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 150.00   94
  8  ω      4.00  52.00   1.00    1.00    --   35.62 -57.00 150.00   48
  9  ω    136.00 177.00   1.00    2.78    --  107.12  30.00  30.00   41
 10  ω     58.00  86.00   1.00    2.78    --  107.12 178.00  90.00   28
 11  ω    127.00 161.00   1.00    2.78    --  107.12 111.00 150.00   34
 12  ω     41.00 120.00   1.00    2.78    --  107.12 -61.00-150.00   79
 13  ω    109.00 166.00   1.00    2.78    --  107.12  61.00-120.00   57
 14  ω     90.00 127.00   1.00    2.78    --  107.12  30.00  30.00   37
 15  ω     98.00 147.00   1.00    2.78    --  107.12 178.00  90.00   49
 16  ω     41.00  83.00   1.00    2.78    --  107.12 -30.00  60.00   42
 17  ω     37.00 129.00   1.00    2.78    --  107.12 -30.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1127025000
_diffrn_orient_matrix_UB_12      -0.0709171000
_diffrn_orient_matrix_UB_13      0.0750467000
_diffrn_orient_matrix_UB_21      0.0783794000
_diffrn_orient_matrix_UB_22      0.1211523000
_diffrn_orient_matrix_UB_23      0.0192234000
_diffrn_orient_matrix_UB_31      -0.0433556000
_diffrn_orient_matrix_UB_32      0.0350716000
_diffrn_orient_matrix_UB_33      0.0851647000
_diffrn_oxdiff_digest_frames     
;
0138c1823b51f60ff0fb5e003d37a42092000381fcb
;
_diffrn_oxdiff_digest_hkl        
;
019a398eb80286f18c446745b2a1daa35fd4ca
;
_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                2644
_reflns_number_total             3141
_reflns_odcompleteness_completeness 99.84
_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 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.147
_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)+(0.0569P)²+1.1686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.7082(2) 0.4881(2) 0.42249(17) 0.0424(6) Uani 1 1 d . . . . .
N1 N 0.66795(17) 0.4156(2) 0.33671(14) 0.0396(5) Uani 1 1 d . . . . .
O1 O 0.91043(18) 0.22015(19) 0.26552(14) 0.0582(5) Uani 1 1 d . . . . .
C2 C 0.6561(3) 0.5024(3) 0.4941(2) 0.0555(7) Uani 1 1 d . . . . .
H2 H 0.5850 0.4581 0.4900 0.067 Uiso 1 1 calc R . . . .
N2 N 0.88828(18) 0.3378(2) 0.12741(16) 0.0451(5) Uani 1 1 d . . . . .
O2 O 0.81572(19) 0.4673(2) -0.00945(14) 0.0622(6) Uani 1 1 d . . . . .
C3 C 0.7136(3) 0.5845(3) 0.5714(2) 0.0684(9) Uani 1 1 d . . . . .
H3 H 0.6798 0.5975 0.6197 0.082 Uiso 1 1 calc R . . . .
N3 N 0.4533(2) 0.4740(3) 0.16663(19) 0.0673(7) Uani 1 1 d . . . . .
H3A H 0.3773 0.4996 0.1340 0.081 Uiso 1 1 d GR . . . .
H3B H 0.4938 0.5339 0.2064 0.081 Uiso 1 1 d GR . . . .
C4 C 0.8219(3) 0.6488(3) 0.5784(2) 0.0707(10) Uani 1 1 d . . . . .
H4 H 0.8587 0.7041 0.6313 0.085 Uiso 1 1 calc R . . . .
C5 C 0.8751(3) 0.6321(3) 0.5091(2) 0.0625(8) Uani 1 1 d . . . . .
H5 H 0.9482 0.6742 0.5156 0.075 Uiso 1 1 calc R . . . .
C6 C 0.8181(2) 0.5512(2) 0.42831(19) 0.0469(6) Uani 1 1 d . . . . .
C7 C 0.8429(2) 0.5126(3) 0.3432(2) 0.0491(6) Uani 1 1 d . . . . .
H7 H 0.9100 0.5385 0.3273 0.059 Uiso 1 1 calc R . . . .
C8 C 0.7516(2) 0.4313(2) 0.28932(17) 0.0407(5) Uani 1 1 d . . . . .
C9 C 0.7341(2) 0.3629(3) 0.19504(17) 0.0429(6) Uani 1 1 d . . . . .
H9 H 0.6676 0.3005 0.1827 0.051 Uiso 1 1 calc R . . . .
C10 C 0.7032(3) 0.4460(3) 0.1017(2) 0.0538(7) Uani 1 1 d . . . . .
H10A H 0.6225 0.4236 0.0516 0.065 Uiso 1 1 calc R . . . .
H10B H 0.7016 0.5339 0.1188 0.065 Uiso 1 1 calc R . . . .
C11 C 0.8052(2) 0.4218(3) 0.06376(18) 0.0470(6) Uani 1 1 d . . . . .
C12 C 0.8538(2) 0.2958(2) 0.20335(18) 0.0437(6) Uani 1 1 d . . . . .
C13 C 0.9999(3) 0.2943(3) 0.1137(2) 0.0617(8) Uani 1 1 d . . . . .
H13A H 1.0689 0.3481 0.1497 0.093 Uiso 1 1 calc GR . . . .
H13B H 0.9862 0.2960 0.0439 0.093 Uiso 1 1 calc GR . . . .
H13C H 1.0185 0.2099 0.1384 0.093 Uiso 1 1 calc GR . . . .
C14 C 0.5601(2) 0.3362(2) 0.30508(17) 0.0391(5) Uani 1 1 d . . . . .
C15 C 0.5607(3) 0.2294(3) 0.3596(2) 0.0510(6) Uani 1 1 d . . . . .
H15 H 0.6311 0.2096 0.4156 0.061 Uiso 1 1 calc R . . . .
C16 C 0.4569(3) 0.1517(3) 0.3313(3) 0.0645(8) Uani 1 1 d . . . . .
H16 H 0.4563 0.0811 0.3690 0.077 Uiso 1 1 calc R . . . .
C17 C 0.3552(3) 0.1806(3) 0.2471(3) 0.0665(9) Uani 1 1 d . . . . .
H17 H 0.2863 0.1275 0.2266 0.080 Uiso 1 1 calc R . . . .
C18 C 0.3532(3) 0.2860(3) 0.1927(2) 0.0614(8) Uani 1 1 d . . . . .
H18 H 0.2833 0.3031 0.1355 0.074 Uiso 1 1 calc R . . . .
C19 C 0.4550(2) 0.3691(3) 0.22159(18) 0.0458(6) 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
C1 N1 1.383(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.411(4) . ?
N1 C8 1.390(3) . ?
N1 C14 1.431(3) . ?
O1 C12 1.200(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
N2 C11 1.378(3) . ?
N2 C12 1.376(3) . ?
N2 C13 1.454(3) . ?
O2 C11 1.211(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(5) . ?
N3 H3A 0.8692 . ?
N3 H3B 0.8679 . ?
N3 C19 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(4) . ?
C6 C7 1.424(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(3) . ?
C8 C9 1.490(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.538(4) . ?
C9 C12 1.521(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.498(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.382(4) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.403(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
N1 C1 C2 129.4(2) . . ?
N1 C1 C6 108.1(2) . . ?
C2 C1 C6 122.5(2) . . ?
C1 N1 C8 108.3(2) . . ?
C1 N1 C14 125.0(2) . . ?
C8 N1 C14 126.71(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2 121.3 . . ?
C11 N2 C13 123.2(2) . . ?
C12 N2 C11 113.8(2) . . ?
C12 N2 C13 123.0(2) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
H3A N3 H3B 108.1 . . ?
C19 N3 H3A 111.2 . . ?
C19 N3 H3B 109.3 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 106.3(2) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 135.5(3) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 C6 108.2(2) . . ?
C8 C7 H7 125.9 . . ?
N1 C8 C9 120.8(2) . . ?
C7 C8 N1 109.2(2) . . ?
C7 C8 C9 130.0(2) . . ?
C8 C9 H9 108.9 . . ?
C8 C9 C10 115.3(2) . . ?
C8 C9 C12 110.62(19) . . ?
C10 C9 H9 108.9 . . ?
C12 C9 H9 108.9 . . ?
C12 C9 C10 104.1(2) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 105.5(2) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
N2 C11 C10 108.3(2) . . ?
O2 C11 N2 124.6(2) . . ?
O2 C11 C10 127.1(3) . . ?
O1 C12 N2 125.1(2) . . ?
O1 C12 C9 126.7(2) . . ?
N2 C12 C9 108.2(2) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 119.2(2) . . ?
C15 C14 C19 120.9(2) . . ?
C19 C14 N1 119.8(2) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.5 . . ?
N3 C19 C14 121.6(2) . . ?
N3 C19 C18 121.0(3) . . ?
C14 C19 C18 117.3(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
C1 N1 C8 C7 -0.4(3) . . . . ?
C1 N1 C8 C9 179.0(2) . . . . ?
C1 N1 C14 C15 -68.7(3) . . . . ?
C1 N1 C14 C19 109.6(3) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C1 C6 C7 C8 0.4(3) . . . . ?
N1 C1 C2 C3 -177.9(3) . . . . ?
N1 C1 C6 C5 179.1(2) . . . . ?
N1 C1 C6 C7 -0.6(3) . . . . ?
N1 C8 C9 C10 113.3(3) . . . . ?
N1 C8 C9 C12 -129.0(2) . . . . ?
N1 C14 C15 C16 179.2(2) . . . . ?
N1 C14 C19 N3 2.1(4) . . . . ?
N1 C14 C19 C18 178.5(2) . . . . ?
C2 C1 N1 C8 -179.5(3) . . . . ?
C2 C1 N1 C14 -1.0(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C5 C6 C7 C8 -179.2(3) . . . . ?
C6 C1 N1 C8 0.6(3) . . . . ?
C6 C1 N1 C14 179.1(2) . . . . ?
C6 C1 C2 C3 1.9(4) . . . . ?
C6 C7 C8 N1 0.0(3) . . . . ?
C6 C7 C8 C9 -179.3(2) . . . . ?
C7 C8 C9 C10 -67.5(3) . . . . ?
C7 C8 C9 C12 50.2(4) . . . . ?
C8 N1 C14 C15 109.5(3) . . . . ?
C8 N1 C14 C19 -72.2(3) . . . . ?
C8 C9 C10 C11 121.2(2) . . . . ?
C8 C9 C12 O1 56.5(3) . . . . ?
C8 C9 C12 N2 -122.7(2) . . . . ?
C9 C10 C11 N2 -1.4(3) . . . . ?
C9 C10 C11 O2 179.0(3) . . . . ?
C10 C9 C12 O1 -179.1(3) . . . . ?
C10 C9 C12 N2 1.7(3) . . . . ?
C11 N2 C12 O1 178.0(2) . . . . ?
C11 N2 C12 C9 -2.8(3) . . . . ?
C12 N2 C11 O2 -177.7(3) . . . . ?
C12 N2 C11 C10 2.7(3) . . . . ?
C12 C9 C10 C11 -0.1(3) . . . . ?
C13 N2 C11 O2 0.2(4) . . . . ?
C13 N2 C11 C10 -179.3(2) . . . . ?
C13 N2 C12 O1 0.0(4) . . . . ?
C13 N2 C12 C9 179.2(2) . . . . ?
C14 N1 C8 C7 -178.8(2) . . . . ?
C14 N1 C8 C9 0.5(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C14 C19 N3 -179.6(3) . . . . ?
C15 C14 C19 C18 -3.2(4) . . . . ?
C15 C16 C17 C18 -2.0(5) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 N3 179.5(3) . . . . ?
C17 C18 C19 C14 3.1(4) . . . . ?
C19 C14 C15 C16 0.9(4) . . . . ?

_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 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.471
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2169507'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N3 O'
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   8.6573(2)
_cell_length_b                   8.6388(2)
_cell_length_c                   19.5245(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.868(2)
_cell_angle_gamma                90
_cell_volume                     1449.73(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2140
_cell_measurement_theta_min      5.3800
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54503
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_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  0.0200
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6282
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.549
_diffrn_reflns_theta_min         4.562
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  32.00   1.00    1.00    --  -35.62  49.00  39.00   85
  2  ω   -104.00 -18.00   1.00    1.00    --  -35.62 -49.00-107.00   86
  3  ω     37.00  62.00   1.00    1.00    --   35.62  49.00  39.00   25
  4  ω     42.00 123.00   1.00    1.56    --  107.12 -49.00-107.00   81
  5  ω    132.00 175.00   1.00    1.56    --  107.12  49.00  39.00   43
  6  ω     90.00 127.00   1.00    1.56    --  107.12  49.00  39.00   37
  7  ω   -107.00 -37.00   1.00    1.00    --  -35.62-178.00 -60.00   70
  8  ω    -88.00 -36.00   1.00    1.00    --  -35.62-178.00  60.00   52
  9  ω    -92.00 -21.00   1.00    1.00    --  -35.62 -57.00-150.00   71
 10  ω     74.00 105.00   1.00    1.00    --   35.62 178.00 -60.00   31
 11  ω      1.00  27.00   1.00    1.00    --   35.62 -49.00-107.00   26
 12  ω     43.00 115.00   1.00    1.56    --  107.12 -45.00  90.00   72
 13  ω     63.00  89.00   1.00    1.56    --  107.12 -95.00  60.00   26
 14  ω    102.00 135.00   1.00    1.56    --  107.12 111.00  90.00   33
 15  ω     39.00  78.00   1.00    1.56    --  107.12-111.00 -60.00   39
 16  ω     43.00  69.00   1.00    1.56    --  107.12 -95.00-180.00   26
 17  ω     84.00 110.00   1.00    1.56    --  107.12 -95.00 -60.00   26
 18  ω    103.00 175.00   1.00    1.56    --  107.12  45.00   0.00   72
 19  ω     37.00 126.00   1.00    1.56    --  107.12 -30.00  30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0619330000
_diffrn_orient_matrix_UB_12      -0.0903177000
_diffrn_orient_matrix_UB_13      0.0656811000
_diffrn_orient_matrix_UB_21      0.1655181000
_diffrn_orient_matrix_UB_22      0.0595022000
_diffrn_orient_matrix_UB_23      -0.0062042000
_diffrn_orient_matrix_UB_31      -0.0300309000
_diffrn_orient_matrix_UB_32      0.1417168000
_diffrn_orient_matrix_UB_33      0.0443474000
_diffrn_oxdiff_digest_frames     
;
010922140c001ab6417a853621523a497e00032a16d
;
_diffrn_oxdiff_digest_hkl        
;
01f26034b01721311714635a5bec2e24773580
;
_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                2274
_reflns_number_total             2751
_reflns_odcompleteness_completeness 99.82
_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 1.171.40.53 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.257
_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)+(0.0350P)²+1.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1474
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.5732(3) 0.4471(3) 0.85174(13) 0.0369(6) Uani 1 1 d . . . . .
N1 N 0.6832(2) 0.5299(2) 0.82005(10) 0.0341(5) Uani 1 1 d . . . . .
O1 O 0.7792(3) 0.5095(3) 0.53060(9) 0.0565(6) Uani 1 1 d . . . . .
C2 C 0.5755(4) 0.3975(4) 0.92011(14) 0.0495(7) Uani 1 1 d . . . . .
H2 H 0.6572 0.4224 0.9536 0.059 Uiso 1 1 calc R . . . .
N2 N 0.8957(2) 0.4809(3) 0.64152(10) 0.0377(5) Uani 1 1 d . . . . .
C3 C 0.4513(4) 0.3100(4) 0.93544(16) 0.0589(9) Uani 1 1 d . . . . .
H3 H 0.4500 0.2748 0.9804 0.071 Uiso 1 1 calc R . . . .
N3 N 0.9804(2) 0.5073(3) 0.75817(10) 0.0362(5) Uani 1 1 d . . . . .
C4 C 0.3281(4) 0.2726(4) 0.88623(18) 0.0603(9) Uani 1 1 d . . . . .
H4 H 0.2460 0.2142 0.8990 0.072 Uiso 1 1 calc R . . . .
C5 C 0.3251(3) 0.3203(4) 0.81890(17) 0.0514(7) Uani 1 1 d . . . . .
H5 H 0.2425 0.2941 0.7860 0.062 Uiso 1 1 calc R . . . .
C6 C 0.4497(3) 0.4095(3) 0.80108(13) 0.0391(6) Uani 1 1 d . . . . .
C7 C 0.4869(3) 0.4740(3) 0.73757(13) 0.0381(6) Uani 1 1 d . . . . .
H7 H 0.4258 0.4681 0.6951 0.046 Uiso 1 1 calc R . . . .
C8 C 0.6265(3) 0.5449(3) 0.75022(12) 0.0310(5) Uani 1 1 d . . . . .
C9 C 0.7278(3) 0.6241(3) 0.70389(12) 0.0328(5) Uani 1 1 d . . . . .
H9 H 0.7487 0.7308 0.7194 0.039 Uiso 1 1 calc R . . . .
C10 C 0.6645(3) 0.6226(3) 0.62715(12) 0.0417(6) Uani 1 1 d . . . . .
H10A H 0.5637 0.5722 0.6202 0.050 Uiso 1 1 calc R . . . .
H10B H 0.6536 0.7273 0.6093 0.050 Uiso 1 1 calc R . . . .
C11 C 0.7816(3) 0.5340(3) 0.59188(13) 0.0408(6) Uani 1 1 d . . . . .
C12 C 0.8787(3) 0.5345(3) 0.70703(12) 0.0318(5) Uani 1 1 d . . . . .
C13 C 1.0311(3) 0.3941(4) 0.62632(15) 0.0500(7) Uani 1 1 d . . . . .
H13A H 1.1223 0.4336 0.6535 0.075 Uiso 1 1 calc GR . . . .
H13B H 1.0427 0.4043 0.5782 0.075 Uiso 1 1 calc GR . . . .
H13C H 1.0180 0.2868 0.6371 0.075 Uiso 1 1 calc GR . . . .
C14 C 0.9649(3) 0.5764(3) 0.82237(12) 0.0356(6) Uani 1 1 d . . . . .
C15 C 1.1019(3) 0.6320(3) 0.85916(14) 0.0460(7) Uani 1 1 d . . . . .
H15 H 1.1954 0.6198 0.8407 0.055 Uiso 1 1 calc R . . . .
C16 C 1.1026(4) 0.7043(4) 0.92194(15) 0.0544(8) Uani 1 1 d . . . . .
H16 H 1.1951 0.7422 0.9450 0.065 Uiso 1 1 calc R . . . .
C17 C 0.9656(4) 0.7203(4) 0.95038(15) 0.0580(9) Uani 1 1 d . . . . .
H17 H 0.9653 0.7692 0.9928 0.070 Uiso 1 1 calc R . . . .
C18 C 0.8290(4) 0.6640(3) 0.91619(13) 0.0484(7) Uani 1 1 d . . . . .
H18 H 0.7370 0.6751 0.9359 0.058 Uiso 1 1 calc R . . . .
C19 C 0.8264(3) 0.5906(3) 0.85245(12) 0.0358(6) 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
C1 N1 1.394(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.405(4) . ?
N1 C8 1.399(3) . ?
N1 C19 1.422(3) . ?
O1 C11 1.213(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
N2 C11 1.377(3) . ?
N2 C12 1.385(3) . ?
N2 C13 1.452(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
N3 C12 1.271(3) . ?
N3 C14 1.409(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(4) . ?
C6 C7 1.431(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.351(3) . ?
C8 C9 1.499(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.533(3) . ?
C9 C12 1.513(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.501(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.397(4) . ?
C14 C19 1.402(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(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
N1 C1 C2 130.4(3) . . ?
N1 C1 C6 108.0(2) . . ?
C2 C1 C6 121.5(3) . . ?
C1 N1 C8 107.5(2) . . ?
C1 N1 C19 126.6(2) . . ?
C8 N1 C19 125.8(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C11 N2 C12 113.1(2) . . ?
C11 N2 C13 123.9(2) . . ?
C12 N2 C13 122.6(2) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(3) . . ?
C4 C3 H3 118.9 . . ?
C12 N3 C14 119.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(3) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 106.8(2) . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 133.5(3) . . ?
C6 C7 H7 126.1 . . ?
C8 C7 C6 107.9(2) . . ?
C8 C7 H7 126.1 . . ?
N1 C8 C9 117.9(2) . . ?
C7 C8 N1 109.8(2) . . ?
C7 C8 C9 132.2(2) . . ?
C8 C9 H9 110.0 . . ?
C8 C9 C10 114.8(2) . . ?
C8 C9 C12 107.84(19) . . ?
C10 C9 H9 110.0 . . ?
C12 C9 H9 110.0 . . ?
C12 C9 C10 104.0(2) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C9 105.7(2) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
O1 C11 N2 124.2(3) . . ?
O1 C11 C10 127.5(3) . . ?
N2 C11 C10 108.3(2) . . ?
N2 C12 C9 108.7(2) . . ?
N3 C12 N2 121.6(2) . . ?
N3 C12 C9 129.7(2) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 116.0(2) . . ?
C15 C14 C19 118.1(2) . . ?
C19 C14 N3 125.9(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 N1 121.6(2) . . ?
C18 C19 N1 119.0(2) . . ?
C18 C19 C14 119.3(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 N1 C8 C7 -0.4(3) . . . . ?
C1 N1 C8 C9 -177.3(2) . . . . ?
C1 N1 C19 C14 136.1(3) . . . . ?
C1 N1 C19 C18 -43.0(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C6 C7 C8 0.6(3) . . . . ?
N1 C1 C2 C3 -176.8(3) . . . . ?
N1 C1 C6 C5 177.6(2) . . . . ?
N1 C1 C6 C7 -0.8(3) . . . . ?
N1 C8 C9 C10 174.5(2) . . . . ?
N1 C8 C9 C12 59.2(3) . . . . ?
C2 C1 N1 C8 177.9(3) . . . . ?
C2 C1 N1 C19 -2.9(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C6 C7 -178.3(2) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
N3 C14 C15 C16 178.8(3) . . . . ?
N3 C14 C19 N1 1.8(4) . . . . ?
N3 C14 C19 C18 -179.1(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C5 C6 C7 C8 -177.5(3) . . . . ?
C6 C1 N1 C8 0.7(3) . . . . ?
C6 C1 N1 C19 179.9(2) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C6 C7 C8 N1 -0.1(3) . . . . ?
C6 C7 C8 C9 176.2(2) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C7 C8 C9 C12 -116.9(3) . . . . ?
C8 N1 C19 C14 -44.9(4) . . . . ?
C8 N1 C19 C18 136.0(3) . . . . ?
C8 C9 C10 C11 -117.7(2) . . . . ?
C8 C9 C12 N2 119.3(2) . . . . ?
C8 C9 C12 N3 -61.1(3) . . . . ?
C9 C10 C11 O1 -177.5(3) . . . . ?
C9 C10 C11 N2 3.3(3) . . . . ?
C10 C9 C12 N2 -3.0(3) . . . . ?
C10 C9 C12 N3 176.7(3) . . . . ?
C11 N2 C12 N3 -174.2(2) . . . . ?
C11 N2 C12 C9 5.5(3) . . . . ?
C12 N2 C11 O1 175.2(3) . . . . ?
C12 N2 C11 C10 -5.5(3) . . . . ?
C12 N3 C14 C15 -139.0(3) . . . . ?
C12 N3 C14 C19 42.4(4) . . . . ?
C12 C9 C10 C11 -0.2(3) . . . . ?
C13 N2 C11 O1 2.7(4) . . . . ?
C13 N2 C11 C10 -178.1(2) . . . . ?
C13 N2 C12 N3 -1.6(4) . . . . ?
C13 N2 C12 C9 178.1(2) . . . . ?
C14 N3 C12 N2 174.2(2) . . . . ?
C14 N3 C12 C9 -5.5(4) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C15 C14 C19 N1 -176.8(2) . . . . ?
C15 C14 C19 C18 2.3(4) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 N1 178.0(3) . . . . ?
C17 C18 C19 C14 -1.1(4) . . . . ?
C19 N1 C8 C7 -179.6(2) . . . . ?
C19 N1 C8 C9 3.5(3) . . . . ?
C19 C14 C15 C16 -2.5(4) . . . . ?

_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 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.357
