# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_usdpn5_49_3_rt_cu
_database_code_depnum_ccdc_archive 'CCDC 2293371'
loop_
_audit_author_name
_audit_author_address
'Puneet Sood'
;IIT Mandi
India
;
_audit_update_record             
;
2023-09-06 deposited with the CCDC.	2024-06-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 N2 O3'
_chemical_formula_sum            'C25 H16 N2 O3'
_chemical_formula_weight         392.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C100  H64  N8  O12  '
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8307(6)
_cell_length_b                   9.9076(4)
_cell_length_c                   16.8625(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.681(5)
_cell_angle_gamma                90
_cell_volume                     1902.95(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3760
_cell_measurement_theta_min      3.8880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 11 0.0855
1 1 -11 0.0855
-6 4 1 0.1034
4 -4 5 0.1217
-4 -5 -2 0.1107
3 -1 -11 0.0772
5 -4 -6 0.1000
1 -6 5 0.1100
-3 -4 8 0.0909
2 0 10 0.0773
-5 -3 7 0.1021
-2 1 11 0.0723
5 5 -1 0.1032
-7 -2 3 0.1056
-5 3 -5 0.0968

_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.165
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.1112 -0.5120 10.8229 -0.9763 -0.0774 0.2021
1.1112 0.5120 -10.8229 0.9763 0.0774 -0.2021
-5.9443 3.9512 0.6432 0.1824 -0.9816 0.0566
4.1881 -3.5418 5.0549 -0.6482 0.7581 0.0719
-3.5196 -5.2234 -2.4315 0.3966 0.2149 0.8925
3.3833 -1.1533 -10.5735 0.8601 0.4677 -0.2037
5.1049 -4.2334 -5.6970 0.3333 0.9425 0.0254
1.1900 -5.5580 4.5904 -0.4697 0.6834 0.5589
-3.3217 -3.9987 8.1572 -0.6188 0.0817 0.7813
1.5004 -0.0836 9.7584 -0.9887 0.1296 -0.0756
-5.3796 -3.2868 7.3138 -0.4527 -0.1872 0.8718
-2.2217 1.3919 10.6826 -0.9210 -0.3819 0.0772
4.7184 5.0050 -0.5009 -0.1695 -0.0709 -0.9830
-7.0855 -2.4709 2.9320 0.0332 -0.4253 0.9045
-4.7861 3.0013 -4.7786 0.6492 -0.7594 0.0429

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5509
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.089
_diffrn_reflns_theta_min         3.881
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  41.00   1.00    1.00    --  -24.78  77.00-180.00   38
  2  ω    -67.00  -1.00   1.00    1.00    --  -24.78  77.00-180.00   66
  3  ω    -56.00 -27.00   1.00    1.00    --  -24.78  77.00 -60.00   29
  4  ω    -22.00  42.00   1.00    1.00    --  -24.78  77.00 -60.00   64
  5  ω    -13.00 131.00   1.00    3.50    --   69.25 -37.00-150.00  144
  6  ω    104.00 146.00   1.00    3.50    --   69.25  77.00-150.00   42
  7  ω    108.00 143.00   1.00    3.50    --   69.25  77.00 -30.00   35
  8  ω    105.00 146.00   1.00    3.50    --   69.25 111.00 -60.00   41
  9  ω     61.00 144.00   1.00    3.50    --   69.25 178.00 120.00   83
 10  ω    113.00 154.00   1.00    3.50    --   69.25 111.00-120.00   41
 11  ω    100.00 175.00   1.00    5.62    --  113.72 138.00 150.00   75
 12  ω     90.00 178.00   1.00    5.62    --  113.72  43.00 -60.00   88
 13  ω     26.00 105.00   1.00    5.62    --  113.72 -89.00  60.00   79
 14  ω    104.00 169.00   1.00    5.62    --  113.72  77.00 -30.00   65
 15  ω    103.00 149.00   1.00    5.62    --  113.72  77.00-120.00   46
 16  ω     29.00  93.00   1.00    5.62    --  113.72 -89.00-180.00   64
 17  ω     36.00 155.00   1.00    5.62    --  113.72 -43.00-180.00  119
 18  ω    143.00 169.00   1.00    5.62    --  113.72  54.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0428763000
_diffrn_orient_matrix_UB_12      -0.0029252000
_diffrn_orient_matrix_UB_13      -0.0947474000
_diffrn_orient_matrix_UB_21      0.0954833000
_diffrn_orient_matrix_UB_22      -0.1044105000
_diffrn_orient_matrix_UB_23      -0.0022900000
_diffrn_orient_matrix_UB_31      -0.0856336000
_diffrn_orient_matrix_UB_32      -0.1152262000
_diffrn_orient_matrix_UB_33      0.0044283000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2809
_reflns_number_total             3471
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.037
_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)+(0.0682P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C2(H2), C13(H13), C19(H19), C1(H1), C25(H25), C4(H4),
 C24(H24), C16(H16), C6(H6), C15(H15), C5(H5), C20(H20), C22(H22), C21(H21)
;
_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
O3 O 0.95933(12) 0.65629(15) 0.59306(9) 0.0679(4) Uani 1 1 d . . . . .
N2 N 0.84949(13) 0.64351(14) 0.59273(8) 0.0513(4) Uani 1 1 d . . . . .
C17 C 0.76763(14) 0.73218(15) 0.55347(9) 0.0425(3) Uani 1 1 d . . . . .
C18 C 0.64859(14) 0.71428(16) 0.55415(9) 0.0447(4) Uani 1 1 d . . . . .
C9 C 0.80562(13) 0.85042(15) 0.51246(9) 0.0415(3) Uani 1 1 d . . . . .
C8 C 0.85043(13) 0.96651(16) 0.56100(10) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.65026(19) 0.3833(2) 0.22889(12) 0.0803(6) Uani 1 1 d . . . . .
C11 C 0.75044(14) 0.73051(17) 0.37641(9) 0.0466(4) Uani 1 1 d . . . . .
C3 C 0.87513(14) 1.08511(16) 0.52075(11) 0.0489(4) Uani 1 1 d . . . . .
C10 C 0.78813(14) 0.85278(16) 0.42802(10) 0.0454(4) Uani 1 1 d . . . . .
O2 O 0.6972(2) 0.2766(2) 0.25395(13) 0.1108(7) Uani 1 1 d . . . . .
C12 C 0.80895(15) 0.60801(17) 0.39801(10) 0.0488(4) Uani 1 1 d . . . . .
H12 H 0.870109 0.602677 0.446008 0.059 Uiso 1 1 calc R U . . .
C7 C 0.87354(15) 0.96791(18) 0.64775(10) 0.0523(4) Uani 1 1 d . . . . .
H7 H 0.856684 0.891875 0.674821 0.063 Uiso 1 1 calc R U . . .
C2 C 0.85351(16) 1.08436(17) 0.43437(12) 0.0548(4) Uani 1 1 d . . . . .
H2 H 0.868549 1.161749 0.407708 0.066 Uiso 1 1 calc R U . . .
C13 C 0.77771(16) 0.49469(18) 0.34944(10) 0.0532(4) Uani 1 1 d . . . . .
H13 H 0.817370 0.413483 0.363851 0.064 Uiso 1 1 calc R U . . .
C23 C 0.61659(17) 0.60034(17) 0.59474(10) 0.0533(4) Uani 1 1 d . . . . .
C19 C 0.56034(15) 0.80604(19) 0.51530(11) 0.0545(4) Uani 1 1 d . . . . .
H19 H 0.579559 0.880784 0.488214 0.065 Uiso 1 1 calc R U . . .
C1 C 0.81146(16) 0.97363(18) 0.38965(10) 0.0532(4) Uani 1 1 d . . . . .
H1 H 0.797442 0.976263 0.332676 0.064 Uiso 1 1 calc R U . . .
O1 O 0.5750(2) 0.3949(3) 0.16460(13) 0.1264(8) Uani 1 1 d . . . . .
C25 C 0.8182(2) 0.53197(18) 0.63248(11) 0.0638(5) Uani 1 1 d . . . . .
H25 H 0.875982 0.471160 0.658976 0.077 Uiso 1 1 calc R U . . .
C14 C 0.68602(17) 0.5051(2) 0.27892(11) 0.0582(5) Uani 1 1 d . . . . .
C4 C 0.92261(17) 1.19851(18) 0.56934(14) 0.0609(5) Uani 1 1 d . . . . .
H4 H 0.938304 1.276764 0.543766 0.073 Uiso 1 1 calc R U . . .
C24 C 0.7067(2) 0.51026(19) 0.63342(12) 0.0656(5) Uani 1 1 d . . . . .
H24 H 0.688536 0.434413 0.660074 0.079 Uiso 1 1 calc R U . . .
C16 C 0.66014(17) 0.7372(2) 0.30339(10) 0.0580(4) Uani 1 1 d . . . . .
H16 H 0.621612 0.818638 0.287427 0.070 Uiso 1 1 calc R U . . .
C6 C 0.92016(17) 1.0791(2) 0.69227(12) 0.0609(5) Uani 1 1 d . . . . .
H6 H 0.935205 1.078062 0.749331 0.073 Uiso 1 1 calc R U . . .
C15 C 0.62761(18) 0.6248(2) 0.25488(11) 0.0653(5) Uani 1 1 d . . . . .
H15 H 0.567038 0.629405 0.206512 0.078 Uiso 1 1 calc R U . . .
C5 C 0.94561(18) 1.1951(2) 0.65246(14) 0.0656(5) Uani 1 1 d . . . . .
H5 H 0.978454 1.270086 0.683374 0.079 Uiso 1 1 calc R U . . .
C20 C 0.44639(18) 0.7866(2) 0.51691(13) 0.0698(5) Uani 1 1 d . . . . .
H20 H 0.389096 0.848502 0.491212 0.084 Uiso 1 1 calc R U . . .
C22 C 0.4978(2) 0.5836(2) 0.59425(13) 0.0718(6) Uani 1 1 d . . . . .
H22 H 0.475881 0.508993 0.620085 0.086 Uiso 1 1 calc R U . . .
C21 C 0.4154(2) 0.6748(3) 0.55672(15) 0.0768(6) Uani 1 1 d . . . . .
H21 H 0.337785 0.662766 0.557490 0.092 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
O3 N2 1.304(2) . ?
N2 C17 1.342(2) . ?
N2 C25 1.393(2) . ?
C17 C18 1.423(2) . ?
C17 C9 1.490(2) . ?
C18 C23 1.423(2) . ?
C18 C19 1.406(2) . ?
C9 C8 1.428(2) . ?
C9 C10 1.382(2) . ?
C8 C3 1.426(2) . ?
C8 C7 1.414(2) . ?
N1 O2 1.215(3) . ?
N1 O1 1.208(3) . ?
N1 C14 1.468(3) . ?
C11 C10 1.488(2) . ?
C11 C12 1.396(2) . ?
C11 C16 1.397(2) . ?
C3 C2 1.409(3) . ?
C3 C4 1.414(3) . ?
C10 C1 1.423(2) . ?
C12 C13 1.380(2) . ?
C7 C6 1.363(3) . ?
C2 C1 1.348(3) . ?
C13 C14 1.380(3) . ?
C23 C24 1.408(3) . ?
C23 C22 1.413(3) . ?
C19 C20 1.369(3) . ?
C25 C24 1.341(3) . ?
C14 C15 1.377(3) . ?
C4 C5 1.354(3) . ?
C16 C15 1.374(3) . ?
C6 C5 1.405(3) . ?
C20 C21 1.394(3) . ?
C22 C21 1.353(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
O3 N2 C17 121.59(14) . . ?
O3 N2 C25 117.97(15) . . ?
C17 N2 C25 120.42(16) . . ?
N2 C17 C18 119.89(14) . . ?
N2 C17 C9 118.39(14) . . ?
C18 C17 C9 121.68(14) . . ?
C17 C18 C23 119.69(15) . . ?
C19 C18 C17 121.86(14) . . ?
C19 C18 C23 118.45(16) . . ?
C8 C9 C17 118.61(13) . . ?
C10 C9 C17 120.75(14) . . ?
C10 C9 C8 120.38(14) . . ?
C3 C8 C9 118.87(14) . . ?
C7 C8 C9 122.62(14) . . ?
C7 C8 C3 118.50(15) . . ?
O2 N1 C14 118.8(2) . . ?
O1 N1 O2 123.5(2) . . ?
O1 N1 C14 117.7(3) . . ?
C12 C11 C10 120.41(14) . . ?
C12 C11 C16 118.58(16) . . ?
C16 C11 C10 120.93(16) . . ?
C2 C3 C8 118.97(15) . . ?
C2 C3 C4 122.40(16) . . ?
C4 C3 C8 118.63(16) . . ?
C9 C10 C11 121.76(14) . . ?
C9 C10 C1 119.28(15) . . ?
C1 C10 C11 118.90(14) . . ?
C13 C12 C11 121.21(16) . . ?
C6 C7 C8 120.96(17) . . ?
C1 C2 C3 121.27(15) . . ?
C14 C13 C12 118.19(18) . . ?
C24 C23 C18 117.33(17) . . ?
C24 C23 C22 123.76(17) . . ?
C22 C23 C18 118.91(18) . . ?
C20 C19 C18 120.72(17) . . ?
C2 C1 C10 121.20(15) . . ?
C24 C25 N2 121.53(17) . . ?
C13 C14 N1 118.1(2) . . ?
C15 C14 N1 119.67(18) . . ?
C15 C14 C13 122.24(17) . . ?
C5 C4 C3 121.15(18) . . ?
C25 C24 C23 121.12(17) . . ?
C15 C16 C11 120.72(19) . . ?
C7 C6 C5 120.36(18) . . ?
C16 C15 C14 119.02(17) . . ?
C4 C5 C6 120.40(18) . . ?
C19 C20 C21 120.6(2) . . ?
C21 C22 C23 120.91(18) . . ?
C22 C21 C20 120.4(2) . . ?

_olex2_date_sample_data_collection 2023-08-28
_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.738
