# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_exp_12660
_database_code_depnum_ccdc_archive 'CCDC 2307357'
loop_
_audit_author_name
_audit_author_address
DBP-HOF
;Guangxi University
China
;
_audit_update_record             
;
2023-11-12 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H22 N4 O4, C2 H7 N'
_chemical_formula_sum            'C36 H29 N5 O4'
_chemical_formula_weight         595.64
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.623(6)
_cell_length_b                   8.325(2)
_cell_length_c                   10.0606(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.746(13)
_cell_angle_gamma                90
_cell_volume                     3039.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6200
_cell_measurement_theta_min      4.0720
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5257
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.497
_diffrn_reflns_theta_max         24.497
_diffrn_reflns_theta_min         3.475
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_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    -29.00  -3.00   1.00   15.00    --  -16.28  77.00  90.00   26
  2  ω    -53.00  70.00   1.00   15.00    --   15.49   0.00 150.00  123
  3  ω    -60.00 -29.00   1.00   15.00    --  -16.28 131.00 128.00   31
  4  ω     -9.00  21.00   1.00   15.00    --  -16.28 -99.00-150.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0007059500
_diffrn_orient_matrix_UB_12      0.0846337500
_diffrn_orient_matrix_UB_13      -0.0073413000
_diffrn_orient_matrix_UB_21      -0.0195336000
_diffrn_orient_matrix_UB_22      0.0033904000
_diffrn_orient_matrix_UB_23      -0.0087654000
_diffrn_orient_matrix_UB_31      0.0002970500
_diffrn_orient_matrix_UB_32      0.0091145500
_diffrn_orient_matrix_UB_33      0.0702336000
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1330
_reflns_number_total             2473
_reflns_odcompleteness_completeness 99.46
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.080
_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)+(0.0284P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C17
 0.8 with sigma of 0.02
 H1B-O1
 0.6 with sigma of 0.02
 H1B-H1B_$1 = H1B-H1B_$1
 2.2 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16), N3(H3)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.24795(9) 0.4131(4) 0.5963(3) 0.0485(10) Uani 1 1 d . . . . .
H1 H 0.2354 0.4504 0.5157 0.058 Uiso 1 1 calc R U . . .
C2 C 0.28502(9) 0.3979(4) 0.6262(3) 0.0470(10) Uani 1 1 d . . . . .
H2 H 0.3022 0.4232 0.5691 0.056 Uiso 1 1 calc R U . . .
C3 C 0.29351(9) 0.3371(4) 0.7592(3) 0.0390(9) Uani 1 1 d . . . . .
C4 C 0.32795(8) 0.3045(4) 0.8323(3) 0.0394(9) Uani 1 1 d . . . . .
C5 C 0.33335(8) 0.2540(4) 0.9666(3) 0.0394(9) Uani 1 1 d . . . . .
C6 C 0.36932(8) 0.2232(5) 1.0455(3) 0.0533(11) Uani 1 1 d . . . . .
H6 H 0.3922 0.2315 1.0158 0.064 Uiso 1 1 calc R U . . .
C7 C 0.36275(8) 0.1809(5) 1.1688(3) 0.0554(11) Uani 1 1 d . . . . .
H7 H 0.3803 0.1545 1.2413 0.066 Uiso 1 1 calc R U . . .
C8 C 0.32333(8) 0.1843(4) 1.1676(3) 0.0384(9) Uani 1 1 d . . . . .
C9 C 0.30556(8) 0.1413(4) 1.2774(3) 0.0438(10) Uani 1 1 d . . . . .
H9 H 0.3212 0.1101 1.3537 0.053 Uiso 1 1 calc R U . . .
C10 C 0.26853(9) 0.1383(4) 1.2896(3) 0.0409(9) Uani 1 1 d . . . . .
C11 C 0.36100(8) 0.3232(4) 0.7592(3) 0.0411(9) Uani 1 1 d . . . . .
C12 C 0.36477(8) 0.2239(4) 0.6494(3) 0.0453(10) Uani 1 1 d . . . . .
H12 H 0.3465 0.1494 0.6204 0.054 Uiso 1 1 calc R U . . .
C13 C 0.39560(9) 0.2362(5) 0.5837(3) 0.0490(10) Uani 1 1 d . . . . .
H13 H 0.3979 0.1686 0.5118 0.059 Uiso 1 1 calc R U . . .
C14 C 0.42305(9) 0.3474(4) 0.6233(3) 0.0417(9) Uani 1 1 d . . . . .
C15 C 0.41961(8) 0.4452(5) 0.7330(3) 0.0526(11) Uani 1 1 d . . . . .
H15 H 0.4379 0.5199 0.7616 0.063 Uiso 1 1 calc R U . . .
C16 C 0.38870(9) 0.4316(5) 0.8002(3) 0.0560(11) Uani 1 1 d . . . . .
H16 H 0.3868 0.4969 0.8740 0.067 Uiso 1 1 calc R U . . .
C17 C 0.45558(9) 0.3657(5) 0.5456(3) 0.0475(10) Uani 1 1 d D . . . .
N1 N 0.26022(7) 0.3177(4) 0.8060(3) 0.0423(8) Uani 1 1 d . . . . .
H1A H 0.2573(7) 0.278(4) 0.879(2) 0.038(9) Uiso 1 1 d . . . . .
N2 N 0.30582(6) 0.2297(3) 1.0447(2) 0.0381(7) Uani 1 1 d . . . . .
O1 O 0.47567(7) 0.4875(4) 0.5730(2) 0.0708(9) Uani 1 1 d D . . . .
O2 O 0.46020(6) 0.2619(3) 0.4598(2) 0.0690(9) Uani 1 1 d . . . . .
C18 C 0.47036(11) 0.0974(7) 0.1784(4) 0.1062(19) Uani 1 1 d . . . . .
H18A H 0.4804 0.0214 0.1212 0.159 Uiso 1 1 calc R U . . .
H18B H 0.4535 0.1673 0.1249 0.159 Uiso 1 1 calc R U . . .
H18C H 0.4576 0.0410 0.2416 0.159 Uiso 1 1 calc R U . . .
N3 N 0.5000 0.1915(6) 0.2500 0.0566(12) Uani 1 2 d S T P . .
H3 H 0.5000 0.2948 0.2500 0.068 Uiso 1 2 calc R U P . .
H1B H 0.476(2) 0.550(7) 0.540(10) 0.50(9) Uiso 1 1 d 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 H1 0.9300 . ?
C1 C2 1.356(4) . ?
C1 C10 1.433(4) 7_557 ?
C2 H2 0.9300 . ?
C2 C3 1.424(4) . ?
C3 C4 1.398(4) . ?
C3 N1 1.375(4) . ?
C4 C5 1.403(4) . ?
C4 C11 1.507(4) . ?
C5 C6 1.466(4) . ?
C5 N2 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.343(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.442(4) . ?
C8 C9 1.402(4) . ?
C8 N2 1.366(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(4) . ?
C10 C1 1.433(4) 7_557 ?
C10 N1 1.377(4) 7_557 ?
C11 C12 1.401(4) . ?
C11 C16 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 C15 1.391(4) . ?
C14 C17 1.518(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.400(4) . ?
C16 H16 0.9300 . ?
C17 O1 1.261(4) . ?
C17 O2 1.249(4) . ?
N1 C10 1.377(4) 7_557 ?
N1 H1A 0.83(2) . ?
O1 H1B 0.62(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 N3 1.449(5) . ?
N3 C18 1.449(5) 2_655 ?
N3 H3 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 125.9 . . ?
C2 C1 C10 108.2(3) . 7_557 ?
C10 C1 H1 125.9 7_557 . ?
C1 C2 H2 125.5 . . ?
C1 C2 C3 109.1(3) . . ?
C3 C2 H2 125.5 . . ?
C4 C3 C2 129.1(3) . . ?
N1 C3 C2 105.8(3) . . ?
N1 C3 C4 125.1(3) . . ?
C3 C4 C5 124.4(2) . . ?
C3 C4 C11 116.7(3) . . ?
C5 C4 C11 118.9(3) . . ?
C4 C5 C6 125.0(3) . . ?
N2 C5 C4 125.2(3) . . ?
N2 C5 C6 109.8(3) . . ?
C5 C6 H6 126.7 . . ?
C7 C6 C5 106.6(3) . . ?
C7 C6 H6 126.7 . . ?
C6 C7 H7 126.6 . . ?
C6 C7 C8 106.9(3) . . ?
C8 C7 H7 126.6 . . ?
C9 C8 C7 123.9(3) . . ?
N2 C8 C7 111.1(2) . . ?
N2 C8 C9 124.9(3) . . ?
C8 C9 H9 115.1 . . ?
C10 C9 C8 129.9(3) . . ?
C10 C9 H9 115.1 . . ?
C9 C10 C1 127.0(3) . 7_557 ?
N1 C10 C1 105.9(3) 7_557 7_557 ?
N1 C10 C9 127.0(3) 7_557 . ?
C12 C11 C4 119.7(3) . . ?
C16 C11 C4 121.9(3) . . ?
C16 C11 C12 118.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 C17 120.6(3) . . ?
C15 C14 C17 120.7(3) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.2(3) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O1 C17 C14 116.3(3) . . ?
O2 C17 C14 118.3(4) . . ?
O2 C17 O1 125.3(3) . . ?
C3 N1 C10 111.1(2) . 7_557 ?
C3 N1 H1A 125.3(19) . . ?
C10 N1 H1A 123.4(19) 7_557 . ?
C8 N2 C5 105.5(2) . . ?
C17 O1 H1B 128(10) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
C18 N3 C18 114.5(6) 2_655 . ?
C18 N3 H3 122.7 2_655 . ?
C18 N3 H3 122.7 . . ?

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
C1 C2 C3 C4 -179.1(4) . . . . ?
C1 C2 C3 N1 -0.2(4) . . . . ?
C2 C3 C4 C5 175.8(3) . . . . ?
C2 C3 C4 C11 -5.3(5) . . . . ?
C2 C3 N1 C10 0.3(4) . . . 7_557 ?
C3 C4 C5 C6 -178.4(3) . . . . ?
C3 C4 C5 N2 -0.1(5) . . . . ?
C3 C4 C11 C12 -63.5(4) . . . . ?
C3 C4 C11 C16 119.0(4) . . . . ?
C4 C3 N1 C10 179.3(3) . . . 7_557 ?
C4 C5 C6 C7 178.7(3) . . . . ?
C4 C5 N2 C8 -179.0(3) . . . . ?
C4 C11 C12 C13 -178.0(3) . . . . ?
C4 C11 C16 C15 178.7(3) . . . . ?
C5 C4 C11 C12 115.4(4) . . . . ?
C5 C4 C11 C16 -62.0(5) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C5 N2 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 177.6(3) . . . . ?
C6 C7 C8 N2 -0.5(4) . . . . ?
C7 C8 C9 C10 -179.6(4) . . . . ?
C7 C8 N2 C5 0.6(4) . . . . ?
C8 C9 C10 C1 177.4(4) . . . 7_557 ?
C8 C9 C10 N1 -1.8(6) . . . 7_557 ?
C9 C8 N2 C5 -177.5(3) . . . . ?
C10 C1 C2 C3 0.0(4) 7_557 . . . ?
C11 C4 C5 C6 2.7(5) . . . . ?
C11 C4 C5 N2 -179.0(3) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C11 C16 C15 1.2(6) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C12 C13 C14 C17 -176.6(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C13 C14 C17 O1 167.7(3) . . . . ?
C13 C14 C17 O2 -11.6(5) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C15 C14 C17 O1 -10.2(5) . . . . ?
C15 C14 C17 O2 170.5(3) . . . . ?
C16 C11 C12 C13 -0.4(5) . . . . ?
C17 C14 C15 C16 177.3(3) . . . . ?
N1 C3 C4 C5 -3.0(6) . . . . ?
N1 C3 C4 C11 175.9(3) . . . . ?
N2 C5 C6 C7 0.2(4) . . . . ?
N2 C8 C9 C10 -1.8(6) . . . . ?


_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 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_230802lxx_0m
_database_code_depnum_ccdc_archive 'CCDC 2308077'
loop_
_audit_author_name
_audit_author_address
DBP-HOF-acid
;Guangxi University
China
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H22 N4 O4, C2 H7 N'
_chemical_formula_sum            'C36 H29 N5 O4'
_chemical_formula_weight         595.64
_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'
# start Validation Reply Form
_vrf_PLAT417_230802lxx_0m        
;
PROBLEM: Short Inter D-H..H-D       H1       ..H1       .       1.11 Ang.  
RESPONSE: This alert is due to the existence of an inversion center near the
 H1 atom and can be reasonably ignored. The quality of our data is so high that 
H1 atoms are able to locate in the electron density peak positions.
;
# end Validation Reply Form
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.466(7)
_cell_length_b                   8.2745(15)
_cell_length_c                   10.0269(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.792(3)
_cell_angle_gamma                90
_cell_volume                     2997.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.695
_cell_measurement_theta_min      2.255
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0408 before and 0.0284 after correction. The Ratio of minimum to maximum transmission is 0.8979. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2264
_reflns_number_total             3403
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.134
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.030
_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)+(0.0631P)²+0.9574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H3A(0.5)
3.a Riding coordinates:
 N3(H3A)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
  C16(H16)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.47529(4) 0.51104(19) 0.57297(15) 0.0703(5) Uani 1 1 d . . . . .
H1 H 0.495372 0.524167 0.546327 0.106 Uiso 1 1 calc R U . . .
O2 O 0.46011(4) 0.73753(18) 0.45963(14) 0.0656(4) Uani 1 1 d . . . . .
N1 N 0.19414(3) 0.72978(16) 0.95541(13) 0.0362(3) Uani 1 1 d . . . . .
N2 N 0.26004(4) 0.68199(17) 0.80635(14) 0.0385(3) Uani 1 1 d . . . . .
H2 H 0.257446 0.716619 0.885398 0.046 Uiso 1 1 calc R U . . .
C1 C 0.16635(4) 0.7551(2) 1.03241(17) 0.0373(4) Uani 1 1 d . . . . .
C2 C 0.13064(5) 0.7228(2) 0.95475(19) 0.0507(5) Uani 1 1 d . . . . .
H2A H 0.107670 0.729975 0.984892 0.061 Uiso 1 1 calc R U . . .
C3 C 0.13711(5) 0.6805(3) 0.8311(2) 0.0515(5) Uani 1 1 d . . . . .
H3 H 0.119489 0.653823 0.758463 0.062 Uiso 1 1 calc R U . . .
C4 C 0.17680(4) 0.6845(2) 0.83228(17) 0.0392(4) Uani 1 1 d . . . . .
C5 C 0.19414(5) 0.6416(2) 0.72136(17) 0.0428(4) Uani 1 1 d . . . . .
H5 H 0.178402 0.611169 0.644620 0.051 Uiso 1 1 calc R U . . .
C6 C 0.23158(5) 0.6382(2) 0.71022(17) 0.0394(4) Uani 1 1 d . . . . .
C7 C 0.24791(5) 0.5869(2) 0.59621(18) 0.0461(4) Uani 1 1 d . . . . .
H7 H 0.235197 0.549665 0.515366 0.055 Uiso 1 1 calc R U . . .
C8 C 0.28515(5) 0.6015(2) 0.62560(18) 0.0456(4) Uani 1 1 d . . . . .
H8 H 0.302342 0.575799 0.568399 0.055 Uiso 1 1 calc R U . . .
C9 C 0.29346(4) 0.6629(2) 0.75884(17) 0.0379(4) Uani 1 1 d . . . . .
C10 C 0.32807(4) 0.6951(2) 0.83227(17) 0.0379(4) Uani 1 1 d . . . . .
C11 C 0.36111(4) 0.6777(2) 0.75967(17) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.38889(5) 0.5676(2) 0.80028(19) 0.0524(5) Uani 1 1 d . . . . .
H12 H 0.387042 0.501204 0.873880 0.063 Uiso 1 1 calc R U . . .
C13 C 0.41959(5) 0.5551(2) 0.73233(19) 0.0522(5) Uani 1 1 d . . . . .
H13 H 0.437973 0.479941 0.760656 0.063 Uiso 1 1 calc R U . . .
C14 C 0.42305(4) 0.6529(2) 0.62344(17) 0.0403(4) Uani 1 1 d . . . . .
C15 C 0.39563(5) 0.7643(2) 0.58313(17) 0.0451(4) Uani 1 1 d . . . . .
H15 H 0.397888 0.832472 0.510954 0.054 Uiso 1 1 calc R U . . .
C16 C 0.36470(5) 0.7754(2) 0.64940(18) 0.0445(4) Uani 1 1 d . . . . .
H16 H 0.346136 0.849216 0.619691 0.053 Uiso 1 1 calc R U . . .
C17 C 0.45522(5) 0.6366(2) 0.54575(18) 0.0474(5) Uani 1 1 d . . . . .
N3 N 0.500000 1.1925(3) 0.750000 0.0563(6) Uani 1 2 d S T P . .
H3A H 0.492060 1.266030 0.799570 0.068 Uiso 0.5 1 d R U P . .
C18 C 0.47011(7) 1.0993(4) 0.6777(3) 0.1027(10) Uani 1 1 d . . . . .
H18A H 0.479857 1.027330 0.616159 0.154 Uiso 1 1 calc R U . . .
H18B H 0.452510 1.171046 0.628545 0.154 Uiso 1 1 calc R U . . .
H18C H 0.458133 1.037701 0.740519 0.154 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 H1 0.8200 . ?
O1 C17 1.279(2) . ?
O2 C17 1.231(2) . ?
N1 C1 1.3708(19) . ?
N1 C4 1.361(2) . ?
N2 H2 0.8600 . ?
N2 C6 1.366(2) . ?
N2 C9 1.3764(19) . ?
C1 C2 1.449(2) . ?
C1 C10 1.406(2) 7_567 ?
C2 H2A 0.9300 . ?
C2 C3 1.340(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.446(2) . ?
C4 C5 1.398(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 C7 1.423(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.355(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.423(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.497(2) . ?
C11 C12 1.382(2) . ?
C11 C16 1.390(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 C15 1.380(2) . ?
C14 C17 1.499(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9300 . ?
N3 H3A 0.8601 2_656 ?
N3 H3A 0.8601 . ?
N3 C18 1.447(3) . ?
N3 C18 1.447(3) 2_656 ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C17 O1 H1 109.5 . . ?
C4 N1 C1 105.36(13) . . ?
C6 N2 H2 124.8 . . ?
C6 N2 C9 110.42(13) . . ?
C9 N2 H2 124.8 . . ?
N1 C1 C2 110.39(15) . . ?
N1 C1 C10 124.54(15) . 7_567 ?
C10 C1 C2 125.07(14) 7_567 . ?
C1 C2 H2A 126.7 . . ?
C3 C2 C1 106.69(15) . . ?
C3 C2 H2A 126.7 . . ?
C2 C3 H3 126.6 . . ?
C2 C3 C4 106.74(16) . . ?
C4 C3 H3 126.6 . . ?
N1 C4 C3 110.80(14) . . ?
N1 C4 C5 125.96(15) . . ?
C5 C4 C3 123.21(17) . . ?
C4 C5 H5 115.6 . . ?
C6 C5 C4 128.79(17) . . ?
C6 C5 H5 115.6 . . ?
N2 C6 C5 126.91(15) . . ?
N2 C6 C7 106.57(14) . . ?
C5 C6 C7 126.52(17) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 C6 108.34(16) . . ?
C8 C7 H7 125.8 . . ?
C7 C8 H8 125.8 . . ?
C7 C8 C9 108.40(15) . . ?
C9 C8 H8 125.8 . . ?
N2 C9 C8 106.26(15) . . ?
N2 C9 C10 125.06(15) . . ?
C10 C9 C8 128.67(15) . . ?
C1 C10 C11 118.48(15) 7_567 . ?
C9 C10 C1 124.49(14) . 7_567 ?
C9 C10 C11 117.02(14) . . ?
C12 C11 C10 121.76(15) . . ?
C12 C11 C16 118.27(15) . . ?
C16 C11 C10 119.96(15) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.76(16) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.68(16) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 118.93(15) . . ?
C13 C14 C17 121.39(16) . . ?
C15 C14 C17 119.65(15) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.53(16) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.82(16) . . ?
C15 C16 H16 119.6 . . ?
O1 C17 C14 115.30(16) . . ?
O2 C17 O1 124.57(16) . . ?
O2 C17 C14 120.09(17) . . ?
H3A N3 H3A 90.0 . 2_656 ?
C18 N3 H3A 112.2 2_656 . ?
C18 N3 H3A 112.17(14) . 2_656 ?
C18 N3 H3A 112.1 . . ?
C18 N3 H3A 112.12(14) 2_656 2_656 ?
C18 N3 C18 115.6(3) . 2_656 ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N1 C1 C2 C3 -0.9(2) . . . . ?
N1 C4 C5 C6 -1.3(3) . . . . ?
N2 C6 C7 C8 -0.3(2) . . . . ?
N2 C9 C10 C1 3.0(3) . . . 7_567 ?
N2 C9 C10 C11 -175.87(15) . . . . ?
C1 N1 C4 C3 -0.14(19) . . . . ?
C1 N1 C4 C5 -178.12(17) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C1 C10 C11 C12 62.4(2) 7_567 . . . ?
C1 C10 C11 C16 -116.65(19) 7_567 . . . ?
C2 C3 C4 N1 -0.4(2) . . . . ?
C2 C3 C4 C5 177.65(17) . . . . ?
C3 C4 C5 C6 -179.08(18) . . . . ?
C4 N1 C1 C2 0.60(19) . . . . ?
C4 N1 C1 C10 -179.57(16) . . . 7_567 ?
C4 C5 C6 N2 -2.3(3) . . . . ?
C4 C5 C6 C7 177.19(18) . . . . ?
C5 C6 C7 C8 -179.85(18) . . . . ?
C6 N2 C9 C8 -0.76(19) . . . . ?
C6 N2 C9 C10 -179.22(16) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 N2 0.6(2) . . . . ?
C7 C8 C9 C10 178.95(18) . . . . ?
C8 C9 C10 C1 -175.16(17) . . . 7_567 ?
C8 C9 C10 C11 6.0(3) . . . . ?
C9 N2 C6 C5 -179.78(17) . . . . ?
C9 N2 C6 C7 0.66(19) . . . . ?
C9 C10 C11 C12 -118.7(2) . . . . ?
C9 C10 C11 C16 62.2(2) . . . . ?
C10 C1 C2 C3 179.31(18) 7_567 . . . ?
C10 C11 C12 C13 -179.13(18) . . . . ?
C10 C11 C16 C15 178.16(17) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C17 -177.60(18) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C13 C14 C17 O1 11.1(3) . . . . ?
C13 C14 C17 O2 -171.16(19) . . . . ?
C14 C15 C16 C11 1.6(3) . . . . ?
C15 C14 C17 O1 -166.82(18) . . . . ?
C15 C14 C17 O2 10.9(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C17 C14 C15 C16 176.65(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
