# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_BPMP
_audit_block_doi                 10.5517/ccdc.csd.cc2gpwhk
_database_code_depnum_ccdc_archive 'CCDC 2285149'
loop_
_audit_author_name
_audit_author_address
'jiang peng'
;shanxi normal university 
China
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_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          ?
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      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                   12.4347(5)
_cell_length_b                   7.2040(3)
_cell_length_c                   33.7027(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3019.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.9300
_cell_measurement_theta_min      4.3900
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            7579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.535
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  64.00   1.00    2.00    --   40.73-125.00   0.00   36
  2  ω     47.00 104.00   1.00    4.00    --  106.95 -94.00 -60.00   57
  3  ω     80.00 160.00   1.00    4.00    --  106.95  61.00 -90.00   80
  4  ω    149.00 178.00   1.00    4.00    --  106.95 125.00-120.00   29
  5  ω     96.00 141.00   1.00    4.00    --  106.95 125.00 -90.00   45
  6  ω     87.00 177.00   1.00    4.00    --  106.95  61.00   0.00   90
  7  ω   -117.00   5.00   1.00    2.00    --  -40.73   0.00-120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0810314000
_diffrn_orient_matrix_UB_12      -0.1487188000
_diffrn_orient_matrix_UB_13      0.0135985000
_diffrn_orient_matrix_UB_21      -0.0564129000
_diffrn_orient_matrix_UB_22      -0.0102316000
_diffrn_orient_matrix_UB_23      0.0406441000
_diffrn_orient_matrix_UB_31      -0.0748019000
_diffrn_orient_matrix_UB_32      -0.1533085000
_diffrn_orient_matrix_UB_33      -0.0159281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2312
_reflns_number_total             2983
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.036
_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)+(0.0769P)²+0.0187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1490
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C3(H3), C1(H1), C9(H9), C7(H7), C4(H4), C13(H13), C16(H16),
 C11(H11), C10(H10), C12(H12), C19(H19), C17(H17), C18(H18)
;
_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 0.59170(11) 0.58508(19) 0.44181(4) 0.0264(3) Uani 1 1 d . . . . .
N1 N 0.73934(13) 0.7187(2) 0.39090(4) 0.0226(4) Uani 1 1 d . . . . .
N2 N 0.72654(13) 0.7892(2) 0.42869(4) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.768723 0.878048 0.437585 0.027 Uiso 1 1 calc R U . . .
N3 N 0.70346(13) 0.9421(2) 0.50137(5) 0.0259(4) Uani 1 1 d . . . . .
C8 C 0.87572(14) 0.6173(3) 0.20494(5) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.83462(15) 0.7268(3) 0.32973(5) 0.0212(4) Uani 1 1 d . . . . .
C14 C 0.64717(14) 0.7180(2) 0.45175(5) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.86262(14) 0.6492(2) 0.24816(5) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.76369(14) 0.6181(3) 0.26712(5) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.704961 0.570741 0.252196 0.026 Uiso 1 1 calc R U . . .
C15 C 0.63179(15) 0.8127(3) 0.49095(5) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.93372(15) 0.7543(3) 0.31135(6) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.992655 0.799968 0.326391 0.028 Uiso 1 1 calc R U . . .
C1 C 0.81957(14) 0.7813(3) 0.37122(6) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.869358 0.863088 0.383525 0.026 Uiso 1 1 calc R U . . .
C9 C 0.95067(14) 0.7179(3) 0.18292(6) 0.0232(4) Uani 1 1 d . . . . .
H9 H 0.994056 0.808387 0.195735 0.028 Uiso 1 1 calc R U . . .
C7 C 0.75000(14) 0.6549(3) 0.30703(5) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.682469 0.631196 0.319197 0.026 Uiso 1 1 calc R U . . .
C4 C 0.94733(15) 0.7156(3) 0.27132(6) 0.0239(4) Uani 1 1 d . . . . .
H4 H 1.015715 0.734842 0.259440 0.029 Uiso 1 1 calc R U . . .
C13 C 0.81176(14) 0.4878(3) 0.18487(6) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.759969 0.418197 0.199282 0.028 Uiso 1 1 calc R U . . .
C16 C 0.54571(15) 0.7594(3) 0.51450(6) 0.0252(4) Uani 1 1 d . . . . .
H16 H 0.495711 0.668791 0.505591 0.030 Uiso 1 1 calc R U . . .
C11 C 0.89865(15) 0.5584(3) 0.12286(5) 0.0284(4) Uani 1 1 d . . . . .
H11 H 0.906821 0.538303 0.095163 0.034 Uiso 1 1 calc R U . . .
C10 C 0.96264(15) 0.6872(3) 0.14235(6) 0.0265(4) Uani 1 1 d . . . . .
H10 H 1.015117 0.755084 0.127884 0.032 Uiso 1 1 calc R U . . .
C12 C 0.82250(15) 0.4592(3) 0.14431(6) 0.0267(4) Uani 1 1 d . . . . .
H12 H 0.777717 0.371621 0.131219 0.032 Uiso 1 1 calc R U . . .
C19 C 0.69153(17) 1.0194(3) 0.53723(6) 0.0301(5) Uani 1 1 d . . . . .
H19 H 0.742105 1.110590 0.545364 0.036 Uiso 1 1 calc R U . . .
C17 C 0.53475(17) 0.8420(3) 0.55139(6) 0.0310(5) Uani 1 1 d . . . . .
H17 H 0.476837 0.808755 0.568354 0.037 Uiso 1 1 calc R U . . .
C18 C 0.60888(18) 0.9728(3) 0.56316(6) 0.0321(5) Uani 1 1 d . . . . .
H18 H 0.603657 1.030136 0.588473 0.039 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 C14 1.227(2) . ?
N1 N2 1.380(2) . ?
N1 C1 1.280(2) . ?
N2 H2 0.8800 . ?
N2 C14 1.357(2) . ?
N3 C15 1.337(3) . ?
N3 C19 1.339(3) . ?
C8 C5 1.484(2) . ?
C8 C9 1.394(3) . ?
C8 C13 1.400(3) . ?
C2 C3 1.393(3) . ?
C2 C1 1.464(2) . ?
C2 C7 1.400(3) . ?
C14 C15 1.499(2) . ?
C5 C6 1.404(2) . ?
C5 C4 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C15 C16 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C1 H1 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.388(3) . ?
C11 C12 1.389(3) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 116.01(16) . . ?
N1 N2 H2 120.9 . . ?
C14 N2 N1 118.24(15) . . ?
C14 N2 H2 120.9 . . ?
C15 N3 C19 116.96(17) . . ?
C9 C8 C5 121.01(17) . . ?
C9 C8 C13 117.96(17) . . ?
C13 C8 C5 121.01(16) . . ?
C3 C2 C1 119.97(17) . . ?
C3 C2 C7 118.29(17) . . ?
C7 C2 C1 121.66(16) . . ?
O1 C14 N2 123.21(17) . . ?
O1 C14 C15 121.62(17) . . ?
N2 C14 C15 115.17(16) . . ?
C6 C5 C8 121.22(16) . . ?
C4 C5 C8 121.29(16) . . ?
C4 C5 C6 117.47(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.36(17) . . ?
C7 C6 H6 119.3 . . ?
N3 C15 C14 117.65(16) . . ?
N3 C15 C16 123.87(17) . . ?
C16 C15 C14 118.47(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.78(17) . . ?
C4 C3 H3 119.6 . . ?
N1 C1 C2 120.01(17) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.74(18) . . ?
C10 C9 H9 119.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.70(16) . . ?
C6 C7 H7 119.7 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.36(17) . . ?
C3 C4 H4 119.3 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.33(18) . . ?
C12 C13 H13 119.3 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.08(18) . . ?
C17 C16 H16 121.0 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.25(17) . . ?
C12 C11 H11 120.4 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.63(18) . . ?
C11 C10 H10 119.7 . . ?
C13 C12 C11 120.07(18) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N3 C19 H19 118.3 . . ?
N3 C19 C18 123.31(19) . . ?
C18 C19 H19 118.3 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.13(18) . . ?
C18 C17 H17 120.4 . . ?
C19 C18 H18 120.7 . . ?
C17 C18 C19 118.62(19) . . ?
C17 C18 H18 120.7 . . ?

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 C14 C15 N3 172.44(17) . . . . ?
O1 C14 C15 C16 -6.5(3) . . . . ?
N1 N2 C14 O1 5.6(3) . . . . ?
N1 N2 C14 C15 -174.78(15) . . . . ?
N2 N1 C1 C2 -174.84(15) . . . . ?
N2 C14 C15 N3 -7.2(2) . . . . ?
N2 C14 C15 C16 173.93(17) . . . . ?
N3 C15 C16 C17 -1.5(3) . . . . ?
N3 C19 C18 C17 -0.6(3) . . . . ?
C8 C5 C6 C7 -177.30(17) . . . . ?
C8 C5 C4 C3 176.76(17) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C8 C13 C12 C11 0.7(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C14 C15 C16 C17 177.29(17) . . . . ?
C5 C8 C9 C10 179.95(17) . . . . ?
C5 C8 C13 C12 179.06(17) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C6 C5 C4 C3 -1.7(3) . . . . ?
C15 N3 C19 C18 -0.7(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C3 C2 C1 N1 -163.66(18) . . . . ?
C3 C2 C7 C6 -2.1(3) . . . . ?
C1 N1 N2 C14 -175.51(16) . . . . ?
C1 C2 C3 C4 -175.45(17) . . . . ?
C1 C2 C7 C6 174.87(17) . . . . ?
C9 C8 C5 C6 151.40(18) . . . . ?
C9 C8 C5 C4 -27.0(3) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C7 C2 C1 N1 19.4(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C13 C8 C5 C6 -27.3(3) . . . . ?
C13 C8 C5 C4 154.30(18) . . . . ?
C13 C8 C9 C10 -1.3(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C12 C11 C10 C9 -0.3(3) . . . . ?
C19 N3 C15 C14 -177.00(17) . . . . ?
C19 N3 C15 C16 1.8(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.602
_oxdiff_exptl_absorpt_empirical_full_min 0.522
