# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_blank_0m
_database_code_depnum_ccdc_archive 'CCDC 2354497'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2024-05-10 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_audit_creation_date             2024-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 N2 O2'
_chemical_formula_sum            'C25 H16 N2 O2'
_chemical_formula_weight         376.40
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2194(12)
_cell_length_b                   10.0506(14)
_cell_length_c                   10.4838(14)
_cell_angle_alpha                101.017(8)
_cell_angle_beta                 101.391(7)
_cell_angle_gamma                93.642(7)
_cell_volume                     929.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.7687.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.001
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2020
_reflns_number_total             3197
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1669
_refine_ls_R_factor_gt           0.1078
_refine_ls_restrained_S_all      1.242
_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)+2.0385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1812
_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), C7(H7), C2(H2A), C16(H16), C25(H25), C3(H3), C21(H21), C12(H12),
 C4(H4), C15(H15), C22(H22), C24(H24), C23(H23), C14(H14), C5(H5), C13(H13)
;
_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
O2 O 0.2656(4) 0.7362(4) 0.0420(3) 0.0447(10) Uani 1 1 d . . . . .
O1 O 0.0969(4) 0.5335(4) 0.1399(4) 0.0525(11) Uani 1 1 d . . . . .
N2 N 0.7817(5) 0.5821(5) 0.1198(4) 0.0455(12) Uani 1 1 d . . . . .
H2 H 0.857679 0.538985 0.110103 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3147(5) 0.7205(5) 0.1531(5) 0.0346(12) Uani 1 1 d . . . . .
C9 C 0.4075(5) 0.6031(5) 0.1734(5) 0.0328(12) Uani 1 1 d . . . . .
C8 C 0.5564(5) 0.6252(5) 0.1541(5) 0.0352(12) Uani 1 1 d . . . . .
C1 C 0.6307(5) 0.7484(5) 0.1325(5) 0.0362(12) Uani 1 1 d . . . . .
C11 C 0.3012(5) 0.8194(5) 0.2734(5) 0.0383(13) Uani 1 1 d . . . . .
C20 C 0.1290(6) 0.4062(5) 0.3072(5) 0.0373(13) Uani 1 1 d . . . . .
C17 C 0.3444(5) 0.4952(5) 0.2122(5) 0.0363(13) Uani 1 1 d . . . . .
C19 C 0.1843(5) 0.4812(5) 0.2149(5) 0.0410(13) Uani 1 1 d . . . . .
C7 C 0.6569(6) 0.5288(6) 0.1442(5) 0.0434(14) Uani 1 1 d . . . . .
H7 H 0.639502 0.439283 0.153246 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5966(6) 0.8818(5) 0.1292(5) 0.0466(14) Uani 1 1 d . . . . .
H2A H 0.505003 0.907948 0.142877 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7714(6) 0.7166(6) 0.1124(5) 0.0414(14) Uani 1 1 d . . . . .
C16 C 0.3576(6) 0.8023(5) 0.4020(5) 0.0439(14) Uani 1 1 d . . . . .
H16 H 0.404518 0.725190 0.414985 0.053 Uiso 1 1 calc R U . . .
C25 C -0.0115(6) 0.3361(5) 0.2688(6) 0.0476(15) Uani 1 1 d . . . . .
H25 H -0.065021 0.327201 0.182011 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6994(6) 0.9731(6) 0.1055(6) 0.0551(16) Uani 1 1 d . . . . .
H3 H 0.675889 1.061117 0.101825 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4293(6) 0.3897(6) 0.2491(6) 0.0531(16) Uani 1 1 d . . . . .
C21 C 0.2079(6) 0.4171(6) 0.4352(5) 0.0496(15) Uani 1 1 d . . . . .
H21 H 0.303501 0.462299 0.461985 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2356(6) 0.9370(6) 0.2576(6) 0.0532(16) Uani 1 1 d . . . . .
H12 H 0.200106 0.951563 0.172556 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8384(7) 0.9376(7) 0.0868(6) 0.0616(18) Uani 1 1 d . . . . .
H4 H 0.906739 1.002811 0.073255 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3441(6) 0.8994(6) 0.5101(6) 0.0527(16) Uani 1 1 d . . . . .
H15 H 0.382154 0.887819 0.595793 0.063 Uiso 1 1 calc R U . . .
N1 N 0.4956(6) 0.3045(6) 0.2776(7) 0.092(2) Uani 1 1 d . . . . .
C22 C 0.1444(7) 0.3605(6) 0.5237(6) 0.0581(17) Uani 1 1 d . . . . .
H22 H 0.197176 0.369046 0.610630 0.070 Uiso 1 1 calc R U . . .
C24 C -0.0725(7) 0.2795(6) 0.3576(6) 0.0579(17) Uani 1 1 d . . . . .
H24 H -0.167110 0.232218 0.330765 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0049(7) 0.2920(6) 0.4852(7) 0.0624(18) Uani 1 1 d . . . . .
H23 H -0.037030 0.254222 0.545625 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2753(7) 1.0120(6) 0.4917(6) 0.0629(18) Uani 1 1 d . . . . .
H14 H 0.263985 1.076042 0.564876 0.075 Uiso 1 1 calc R U . . .
C5 C 0.8758(6) 0.8088(7) 0.0881(6) 0.0586(17) Uani 1 1 d . . . . .
H5 H 0.967361 0.783686 0.073202 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2226(7) 1.0316(6) 0.3656(7) 0.0675(19) Uani 1 1 d . . . . .
H13 H 0.177619 1.109900 0.353705 0.081 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
O2 C10 1.207(5) . ?
O1 C19 1.227(6) . ?
N2 H2 0.8600 . ?
N2 C7 1.328(6) . ?
N2 C6 1.377(6) . ?
C10 C9 1.524(6) . ?
C10 C11 1.481(7) . ?
C9 C8 1.436(6) . ?
C9 C17 1.365(7) . ?
C8 C1 1.454(7) . ?
C8 C7 1.387(6) . ?
C1 C2 1.402(7) . ?
C1 C6 1.402(6) . ?
C11 C16 1.393(7) . ?
C11 C12 1.384(7) . ?
C20 C19 1.480(7) . ?
C20 C25 1.381(7) . ?
C20 C21 1.375(7) . ?
C17 C19 1.480(7) . ?
C17 C18 1.424(7) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.368(7) . ?
C6 C5 1.386(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.379(7) . ?
C25 H25 0.9300 . ?
C25 C24 1.369(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C18 N1 1.135(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(8) . ?
C15 H15 0.9300 . ?
C15 C14 1.359(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(8) . ?
C24 H24 0.9300 . ?
C24 C23 1.365(8) . ?
C23 H23 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.371(8) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 H2 125.0 . . ?
C7 N2 C6 110.1(4) . . ?
C6 N2 H2 125.0 . . ?
O2 C10 C9 119.9(4) . . ?
O2 C10 C11 122.5(5) . . ?
C11 C10 C9 117.4(4) . . ?
C8 C9 C10 113.8(4) . . ?
C17 C9 C10 118.0(4) . . ?
C17 C9 C8 128.2(4) . . ?
C9 C8 C1 128.2(4) . . ?
C7 C8 C9 126.4(5) . . ?
C7 C8 C1 105.3(4) . . ?
C2 C1 C8 136.4(5) . . ?
C6 C1 C8 106.4(4) . . ?
C6 C1 C2 117.2(5) . . ?
C16 C11 C10 122.9(5) . . ?
C12 C11 C10 118.6(5) . . ?
C12 C11 C16 118.4(5) . . ?
C25 C20 C19 119.2(5) . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 C25 119.3(5) . . ?
C9 C17 C19 121.4(4) . . ?
C9 C17 C18 121.4(5) . . ?
C18 C17 C19 117.2(5) . . ?
O1 C19 C20 119.8(5) . . ?
O1 C19 C17 119.3(5) . . ?
C20 C19 C17 120.9(5) . . ?
N2 C7 C8 110.5(5) . . ?
N2 C7 H7 124.7 . . ?
C8 C7 H7 124.7 . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2A 120.3 . . ?
N2 C6 C1 107.6(5) . . ?
N2 C6 C5 128.7(5) . . ?
C5 C6 C1 123.7(5) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(5) . . ?
C15 C16 H16 119.9 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.4(6) . . ?
C24 C25 H25 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
N1 C18 C17 179.2(8) . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(6) . . ?
C22 C21 H21 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(6) . . ?
C23 C22 H22 119.6 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.3(6) . . ?
C23 C24 H24 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(6) . . ?
C13 C14 H14 119.9 . . ?
C6 C5 H5 121.4 . . ?
C4 C5 C6 117.2(5) . . ?
C4 C5 H5 121.4 . . ?
C12 C13 C14 120.4(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

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
O2 C10 C9 C8 75.6(6) . . . . ?
O2 C10 C9 C17 -107.2(6) . . . . ?
O2 C10 C11 C16 -179.9(5) . . . . ?
O2 C10 C11 C12 -2.9(8) . . . . ?
N2 C6 C5 C4 -179.5(6) . . . . ?
C10 C9 C8 C1 7.1(7) . . . . ?
C10 C9 C8 C7 -168.6(5) . . . . ?
C10 C9 C17 C19 9.2(7) . . . . ?
C10 C9 C17 C18 -172.1(5) . . . . ?
C10 C11 C16 C15 178.7(5) . . . . ?
C10 C11 C12 C13 -179.1(5) . . . . ?
C9 C10 C11 C16 -5.9(7) . . . . ?
C9 C10 C11 C12 171.1(5) . . . . ?
C9 C8 C1 C2 3.9(10) . . . . ?
C9 C8 C1 C6 -177.0(5) . . . . ?
C9 C8 C7 N2 176.8(5) . . . . ?
C9 C17 C19 O1 26.7(8) . . . . ?
C9 C17 C19 C20 -152.8(5) . . . . ?
C8 C9 C17 C19 -174.0(5) . . . . ?
C8 C9 C17 C18 4.7(8) . . . . ?
C8 C1 C2 C3 179.7(6) . . . . ?
C8 C1 C6 N2 0.6(6) . . . . ?
C8 C1 C6 C5 179.8(5) . . . . ?
C1 C8 C7 N2 0.3(6) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C1 C6 C5 C4 1.5(9) . . . . ?
C11 C10 C9 C8 -98.6(5) . . . . ?
C11 C10 C9 C17 78.7(6) . . . . ?
C11 C16 C15 C14 0.2(8) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
C20 C25 C24 C23 0.1(9) . . . . ?
C20 C21 C22 C23 1.0(9) . . . . ?
C17 C9 C8 C1 -169.8(5) . . . . ?
C17 C9 C8 C7 14.5(8) . . . . ?
C19 C20 C25 C24 -172.2(5) . . . . ?
C19 C20 C21 C22 171.5(5) . . . . ?
C7 N2 C6 C1 -0.5(6) . . . . ?
C7 N2 C6 C5 -179.6(5) . . . . ?
C7 C8 C1 C2 -179.7(6) . . . . ?
C7 C8 C1 C6 -0.6(5) . . . . ?
C2 C1 C6 N2 179.9(5) . . . . ?
C2 C1 C6 C5 -0.9(8) . . . . ?
C2 C3 C4 C5 1.7(10) . . . . ?
C6 N2 C7 C8 0.1(6) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C16 C11 C12 C13 -2.0(9) . . . . ?
C16 C15 C14 C13 -1.8(9) . . . . ?
C25 C20 C19 O1 32.9(7) . . . . ?
C25 C20 C19 C17 -147.6(5) . . . . ?
C25 C20 C21 C22 -1.4(8) . . . . ?
C25 C24 C23 C22 -0.6(9) . . . . ?
C3 C4 C5 C6 -1.8(9) . . . . ?
C18 C17 C19 O1 -152.0(5) . . . . ?
C18 C17 C19 C20 28.5(7) . . . . ?
C21 C20 C19 O1 -140.1(5) . . . . ?
C21 C20 C19 C17 39.5(7) . . . . ?
C21 C20 C25 C24 0.9(8) . . . . ?
C21 C22 C23 C24 0.0(9) . . . . ?
C12 C11 C16 C15 1.7(8) . . . . ?
C15 C14 C13 C12 1.5(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nm_f_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2361275'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2024-06-07 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_audit_creation_date             2024-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N3 O2, 1[C3H6O2], 1[]'
_chemical_formula_sum            'C19 H13 N3 O2'
_chemical_formula_weight         315.32
_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           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                   10.4772(6)
_cell_length_b                   22.4464(13)
_cell_length_c                   9.0718(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.262(2)
_cell_angle_gamma                90
_cell_volume                     2120.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.027
_cell_measurement_theta_min      2.434
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0996 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.8006.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    0.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.123
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20924
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3518
_reflns_number_total             4323
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.034
_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)+(0.1398P)²+0.8403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2339
_refine_ls_wR_factor_ref         0.2429
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C12(H12), C7(H7), C19(H19), C10(H10), C8(H8), C9(H9), C18(H18),
 C15(H15), C17(H17), C16(H16)
2.b 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
O2 O 0.63379(17) 0.52419(9) 0.69658(16) 0.0645(5) Uani 1 1 d . . . . .
O1 O 0.52088(15) 0.56707(10) 0.22151(18) 0.0671(5) Uani 1 1 d . . . . .
H1 H 0.481834 0.536524 0.237765 0.101 Uiso 1 1 calc R U . . .
N3 N 0.7821(2) 0.47909(10) -0.0375(2) 0.0623(6) Uani 1 1 d . . . . .
H3 H 0.763926 0.479866 -0.132235 0.075 Uiso 1 1 calc R U . . .
N1 N 0.5933(2) 0.57492(12) 0.4768(2) 0.0638(6) Uani 1 1 d . . . . .
C6 C 0.8780(2) 0.45680(10) 0.1903(2) 0.0506(5) Uani 1 1 d . . . . .
C14 C 0.7007(2) 0.62901(11) 0.2897(2) 0.0561(6) Uani 1 1 d . . . . .
C4 C 0.7162(2) 0.51694(10) 0.3324(2) 0.0496(5) Uani 1 1 d . . . . .
C5 C 0.7701(2) 0.49569(10) 0.2036(2) 0.0498(5) Uani 1 1 d . . . . .
C2 C 0.7254(2) 0.49593(11) 0.4745(2) 0.0521(5) Uani 1 1 d . . . . .
C1 C 0.6482(2) 0.53244(11) 0.5638(2) 0.0540(5) Uani 1 1 d . . . . .
C12 C 0.7179(2) 0.50861(12) 0.0587(2) 0.0590(6) Uani 1 1 d . . . . .
H12 H 0.648859 0.533965 0.033135 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9782(2) 0.43247(11) 0.2877(3) 0.0595(6) Uani 1 1 d . . . . .
H7 H 0.981711 0.439261 0.389224 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8817(2) 0.44722(10) 0.0364(2) 0.0542(5) Uani 1 1 d . . . . .
N2 N 0.8334(3) 0.40500(13) 0.6041(3) 0.0925(8) Uani 1 1 d . . . . .
C13 C 0.6295(2) 0.57228(11) 0.3254(2) 0.0545(6) Uani 1 1 d . . . . .
C3 C 0.7862(3) 0.44477(12) 0.5413(2) 0.0630(6) Uani 1 1 d . . . . .
C19 C 0.8290(3) 0.63637(13) 0.3368(3) 0.0720(7) Uani 1 1 d . . . . .
H19 H 0.873243 0.605918 0.389826 0.086 Uiso 1 1 calc R U . . .
C10 C 0.9755(3) 0.41300(12) -0.0196(3) 0.0670(7) Uani 1 1 d . . . . .
H10 H 0.975064 0.406994 -0.121064 0.080 Uiso 1 1 calc R U . . .
C8 C 1.0705(3) 0.39875(13) 0.2319(3) 0.0701(7) Uani 1 1 d . . . . .
H8 H 1.135934 0.382340 0.296880 0.084 Uiso 1 1 calc R U . . .
C9 C 1.0691(3) 0.38827(13) 0.0795(3) 0.0724(7) Uani 1 1 d . . . . .
H9 H 1.132016 0.364364 0.045160 0.087 Uiso 1 1 calc R U . . .
C18 C 0.8941(4) 0.68801(15) 0.3071(4) 0.0883(9) Uani 1 1 d . . . . .
H18 H 0.981123 0.691953 0.339064 0.106 Uiso 1 1 calc R U . . .
C15 C 0.6379(3) 0.67504(16) 0.2134(5) 0.0968(11) Uani 1 1 d . . . . .
H15 H 0.550758 0.671597 0.181793 0.116 Uiso 1 1 calc R U . . .
C17 C 0.8297(4) 0.73267(15) 0.2309(5) 0.1023(12) Uani 1 1 d . . . . .
H17 H 0.872815 0.767570 0.211667 0.123 Uiso 1 1 calc R U . . .
C16 C 0.7033(5) 0.72711(17) 0.1825(6) 0.1255(16) Uani 1 1 d . . . . .
H16 H 0.660279 0.757751 0.128903 0.151 Uiso 1 1 calc R U . . .
H1A H 0.548(4) 0.5947(16) 0.510(4) 0.086(11) Uiso 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
O2 C1 1.244(2) . ?
O1 H1 0.8200 . ?
O1 C13 1.402(3) . ?
N3 H3 0.8600 . ?
N3 C12 1.334(3) . ?
N3 C11 1.378(3) . ?
N1 C1 1.328(3) . ?
N1 C13 1.465(3) . ?
N1 H1A 0.74(4) . ?
C6 C5 1.444(3) . ?
C6 C7 1.407(3) . ?
C6 C11 1.417(3) . ?
C14 C13 1.528(3) . ?
C14 C19 1.376(4) . ?
C14 C15 1.371(4) . ?
C4 C5 1.434(3) . ?
C4 C2 1.366(3) . ?
C4 C13 1.536(3) . ?
C5 C12 1.398(3) . ?
C2 C1 1.457(3) . ?
C2 C3 1.417(3) . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.368(4) . ?
C11 C10 1.386(4) . ?
N2 C3 1.142(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.401(4) . ?
C9 H9 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.355(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.399(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.355(6) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 109.5 . . ?
C12 N3 H3 124.8 . . ?
C12 N3 C11 110.40(18) . . ?
C11 N3 H3 124.8 . . ?
C1 N1 C13 112.9(2) . . ?
C1 N1 H1A 117(3) . . ?
C13 N1 H1A 130(3) . . ?
C7 C6 C5 136.0(2) . . ?
C7 C6 C11 117.4(2) . . ?
C11 C6 C5 106.28(19) . . ?
C19 C14 C13 121.2(2) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 C19 117.7(3) . . ?
C5 C4 C13 121.26(18) . . ?
C2 C4 C5 131.4(2) . . ?
C2 C4 C13 107.38(19) . . ?
C4 C5 C6 130.61(19) . . ?
C12 C5 C6 106.0(2) . . ?
C12 C5 C4 123.3(2) . . ?
C4 C2 C1 110.1(2) . . ?
C4 C2 C3 131.7(2) . . ?
C3 C2 C1 117.97(19) . . ?
O2 C1 N1 126.3(2) . . ?
O2 C1 C2 126.0(2) . . ?
N1 C1 C2 107.69(19) . . ?
N3 C12 C5 109.8(2) . . ?
N3 C12 H12 125.1 . . ?
C5 C12 H12 125.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
N3 C11 C6 107.4(2) . . ?
N3 C11 C10 129.7(2) . . ?
C10 C11 C6 122.8(2) . . ?
O1 C13 N1 111.07(18) . . ?
O1 C13 C14 107.83(18) . . ?
O1 C13 C4 113.2(2) . . ?
N1 C13 C14 110.3(2) . . ?
N1 C13 C4 101.90(17) . . ?
C14 C13 C4 112.52(18) . . ?
N2 C3 C2 175.4(3) . . ?
C14 C19 H19 119.2 . . ?
C14 C19 C18 121.7(3) . . ?
C18 C19 H19 119.2 . . ?
C11 C10 H10 121.0 . . ?
C9 C10 C11 117.9(2) . . ?
C9 C10 H10 121.0 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.3(3) . . ?
C17 C18 H18 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?

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
N3 C11 C10 C9 176.4(2) . . . . ?
C6 C5 C12 N3 2.4(3) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C6 C11 C10 C9 -0.9(4) . . . . ?
C14 C19 C18 C17 0.6(5) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C4 C5 C12 N3 -175.1(2) . . . . ?
C4 C2 C1 O2 178.2(2) . . . . ?
C4 C2 C1 N1 -0.1(3) . . . . ?
C5 C6 C7 C8 -176.3(3) . . . . ?
C5 C6 C11 N3 0.5(2) . . . . ?
C5 C6 C11 C10 178.3(2) . . . . ?
C5 C4 C2 C1 -177.9(2) . . . . ?
C5 C4 C2 C3 -3.2(4) . . . . ?
C5 C4 C13 O1 58.0(3) . . . . ?
C5 C4 C13 N1 177.28(19) . . . . ?
C5 C4 C13 C14 -64.6(3) . . . . ?
C2 C4 C5 C6 -20.1(4) . . . . ?
C2 C4 C5 C12 156.7(2) . . . . ?
C2 C4 C13 O1 -121.38(19) . . . . ?
C2 C4 C13 N1 -2.0(2) . . . . ?
C2 C4 C13 C14 116.1(2) . . . . ?
C1 N1 C13 O1 122.9(2) . . . . ?
C1 N1 C13 C14 -117.6(2) . . . . ?
C1 N1 C13 C4 2.1(3) . . . . ?
C12 N3 C11 C6 1.0(3) . . . . ?
C12 N3 C11 C10 -176.6(3) . . . . ?
C7 C6 C5 C4 -10.7(4) . . . . ?
C7 C6 C5 C12 172.1(3) . . . . ?
C7 C6 C11 N3 -174.7(2) . . . . ?
C7 C6 C11 C10 3.1(3) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
C11 N3 C12 C5 -2.2(3) . . . . ?
C11 C6 C5 C4 175.6(2) . . . . ?
C11 C6 C5 C12 -1.7(2) . . . . ?
C11 C6 C7 C8 -3.0(3) . . . . ?
C11 C10 C9 C8 -1.5(4) . . . . ?
C13 N1 C1 O2 -179.6(2) . . . . ?
C13 N1 C1 C2 -1.4(3) . . . . ?
C13 C14 C19 C18 -179.0(3) . . . . ?
C13 C14 C15 C16 179.3(4) . . . . ?
C13 C4 C5 C6 160.7(2) . . . . ?
C13 C4 C5 C12 -22.4(3) . . . . ?
C13 C4 C2 C1 1.4(2) . . . . ?
C13 C4 C2 C3 176.0(3) . . . . ?
C3 C2 C1 O2 2.7(4) . . . . ?
C3 C2 C1 N1 -175.5(2) . . . . ?
C19 C14 C13 O1 -157.9(2) . . . . ?
C19 C14 C13 N1 80.6(3) . . . . ?
C19 C14 C13 C4 -32.4(3) . . . . ?
C19 C14 C15 C16 1.1(6) . . . . ?
C19 C18 C17 C16 -0.7(6) . . . . ?
C18 C17 C16 C15 1.0(7) . . . . ?
C15 C14 C13 O1 24.0(3) . . . . ?
C15 C14 C13 N1 -97.5(3) . . . . ?
C15 C14 C13 C4 149.5(3) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.340 0.250 -0.157 369.2 90.5 '2 C3H6O2,2 '
2 0.340 0.750 -0.959 369.2 90.5 '2 C3H6O2,2 '

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_NM32
_database_code_depnum_ccdc_archive 'CCDC 2376014'
loop_
_audit_author_name
_audit_author_address
'Sudhadevi Antharjanam'
;Sophisticated Analytical Instrument Facility, IIT Madras
India
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 N3 O [+ solvent]'

_chemical_formula_sum            'C20 H13 N3 O'
_chemical_formula_weight         311.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   13.5858(8)
_cell_length_b                   7.0142(4)
_cell_length_c                   19.7041(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.905(2)
_cell_angle_gamma                90
_cell_volume                     1867.71(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      29.86
_exptl_crystal_description       block
_exptl_crystal_colour            orange


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'




_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49056
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3285
_reflns_number_gt                2633
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'


_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0931P)²+0.6535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7721(2) 0.4536(5) 0.34778(16) 0.0888(9) Uani 1 1 d . . . . .
H1 H 0.743307 0.569920 0.356844 0.107 Uiso 1 1 calc R U . . .
C2 C 0.8550(3) 0.4495(8) 0.3112(2) 0.1232(15) Uani 1 1 d . . . . .
H2 H 0.880524 0.562487 0.295586 0.148 Uiso 1 1 calc R U . . .
C3 C 0.8975(3) 0.2831(10) 0.2987(2) 0.1362(19) Uani 1 1 d . . . . .
H3 H 0.952672 0.280300 0.274468 0.163 Uiso 1 1 calc R U . . .
C4 C 0.8602(4) 0.1186(9) 0.3214(3) 0.146(2) Uani 1 1 d . . . . .
H4 H 0.890468 0.003603 0.312534 0.175 Uiso 1 1 calc R U . . .
C5 C 0.7779(3) 0.1180(6) 0.3576(2) 0.1056(12) Uani 1 1 d . . . . .
H5 H 0.753231 0.004178 0.373149 0.127 Uiso 1 1 calc R U . . .
C6 C 0.73328(18) 0.2901(4) 0.37018(13) 0.0619(7) Uani 1 1 d . . . . .
C7 C 0.64593(17) 0.2875(3) 0.40878(12) 0.0519(6) Uani 1 1 d . . . . .
C8 C 0.59717(15) 0.4769(3) 0.42201(10) 0.0443(5) Uani 1 1 d . . . . .
C9 C 0.52410(15) 0.5315(3) 0.37233(10) 0.0461(5) Uani 1 1 d . . . . .
C10 C 0.49965(17) 0.4121(3) 0.31386(12) 0.0544(6) Uani 1 1 d . . . . .
C11 C 0.46926(17) 0.7038(3) 0.37272(11) 0.0501(5) Uani 1 1 d . . . . .
C12 C 0.63110(15) 0.5742(3) 0.48367(10) 0.0430(5) Uani 1 1 d . . . . .
C13 C 0.59881(15) 0.7508(3) 0.50471(11) 0.0465(5) Uani 1 1 d . . . . .
H13 H 0.550913 0.825302 0.480194 0.056 Uiso 1 1 calc R U . . .
C14 C 0.71269(15) 0.6554(3) 0.58686(11) 0.0474(5) Uani 1 1 d . . . . .
C15 C 0.77623(17) 0.6517(4) 0.64759(12) 0.0582(6) Uani 1 1 d . . . . .
C16 C 0.83411(19) 0.4897(4) 0.65682(13) 0.0675(7) Uani 1 1 d . . . . .
H16 H 0.878292 0.479114 0.695939 0.081 Uiso 1 1 calc R U . . .
C17 C 0.8283(2) 0.3429(4) 0.60964(14) 0.0705(8) Uani 1 1 d . . . . .
H17 H 0.867992 0.235860 0.618438 0.085 Uiso 1 1 calc R U . . .
C18 C 0.76553(18) 0.3501(4) 0.54992(13) 0.0599(6) Uani 1 1 d . . . . .
H18 H 0.763262 0.250511 0.518649 0.072 Uiso 1 1 calc R U . . .
C19 C 0.70544(15) 0.5110(3) 0.53762(10) 0.0466(5) Uani 1 1 d . . . . .
C20 C 0.7803(2) 0.8130(5) 0.69773(14) 0.0832(9) Uani 1 1 d . . . . .
H20A H 0.734170 0.910109 0.681199 0.125 Uiso 1 1 calc R U . . .
H20B H 0.763469 0.766756 0.740914 0.125 Uiso 1 1 calc R U . . .
H20C H 0.845956 0.865286 0.703184 0.125 Uiso 1 1 calc R U . . .
N1 N 0.64616(14) 0.7981(3) 0.56490(10) 0.0516(5) Uani 1 1 d . . . . .
N2 N 0.42632(17) 0.8441(3) 0.37192(11) 0.0684(6) Uani 1 1 d . . . . .
N3 N 0.48098(18) 0.3173(4) 0.26724(12) 0.0795(7) Uani 1 1 d . . . . .
O1 O 0.61101(14) 0.1431(2) 0.42988(11) 0.0758(6) Uani 1 1 d . . . . .
H1A H 0.635(2) 0.905(4) 0.5900(14) 0.075(8) Uiso 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 C6 1.355(4) . ?
C1 C2 1.398(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.336(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(3) . ?
C7 O1 1.210(3) . ?
C7 C8 1.519(3) . ?
C8 C9 1.375(3) . ?
C8 C12 1.428(3) . ?
C9 C11 1.421(3) . ?
C9 C10 1.435(3) . ?
C10 N3 1.142(3) . ?
C11 N2 1.143(3) . ?
C12 C13 1.391(3) . ?
C12 C19 1.458(3) . ?
C13 N1 1.332(3) . ?
C13 H13 0.9300 . ?
C14 N1 1.388(3) . ?
C14 C19 1.399(3) . ?
C14 C15 1.402(3) . ?
C15 C16 1.383(4) . ?
C15 C20 1.499(4) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(3) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1A 0.92(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
C6 C1 C2 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 121.4(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 122.6(2) . . ?
C5 C6 C7 118.2(3) . . ?
O1 C7 C6 123.5(2) . . ?
O1 C7 C8 118.7(2) . . ?
C6 C7 C8 117.8(2) . . ?
C9 C8 C12 128.2(2) . . ?
C9 C8 C7 114.64(18) . . ?
C12 C8 C7 117.12(18) . . ?
C8 C9 C11 125.01(19) . . ?
C8 C9 C10 120.0(2) . . ?
C11 C9 C10 115.00(19) . . ?
N3 C10 C9 179.4(3) . . ?
N2 C11 C9 178.5(3) . . ?
C13 C12 C8 126.51(18) . . ?
C13 C12 C19 105.65(17) . . ?
C8 C12 C19 127.85(19) . . ?
N1 C13 C12 110.42(18) . . ?
N1 C13 H13 124.8 . . ?
C12 C13 H13 124.8 . . ?
N1 C14 C19 108.00(18) . . ?
N1 C14 C15 127.1(2) . . ?
C19 C14 C15 124.9(2) . . ?
C16 C15 C14 114.8(2) . . ?
C16 C15 C20 123.4(2) . . ?
C14 C15 C20 121.8(2) . . ?
C15 C16 C17 122.1(2) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 122.1(2) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C14 C19 C18 117.7(2) . . ?
C14 C19 C12 106.22(18) . . ?
C18 C19 C12 136.0(2) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 N1 C14 109.71(19) . . ?
C13 N1 H1A 126.5(17) . . ?
C14 N1 H1A 123.7(17) . . ?

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
C6 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C1 C6 C7 O1 -179.1(3) . . . . ?
C5 C6 C7 O1 -0.2(4) . . . . ?
C1 C6 C7 C8 1.4(4) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
O1 C7 C8 C9 -89.8(3) . . . . ?
C6 C7 C8 C9 89.7(2) . . . . ?
O1 C7 C8 C12 89.5(3) . . . . ?
C6 C7 C8 C12 -91.0(2) . . . . ?
C12 C8 C9 C11 2.0(4) . . . . ?
C7 C8 C9 C11 -178.8(2) . . . . ?
C12 C8 C9 C10 -179.3(2) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C9 C8 C12 C13 -2.8(3) . . . . ?
C7 C8 C12 C13 178.0(2) . . . . ?
C9 C8 C12 C19 176.8(2) . . . . ?
C7 C8 C12 C19 -2.3(3) . . . . ?
C8 C12 C13 N1 179.8(2) . . . . ?
C19 C12 C13 N1 0.1(2) . . . . ?
N1 C14 C15 C16 179.3(2) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
N1 C14 C15 C20 -1.0(4) . . . . ?
C19 C14 C15 C20 179.5(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C20 C15 C16 C17 179.8(3) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
N1 C14 C19 C18 -179.1(2) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
N1 C14 C19 C12 0.5(2) . . . . ?
C15 C14 C19 C12 -180.0(2) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C17 C18 C19 C12 -179.5(2) . . . . ?
C13 C12 C19 C14 -0.4(2) . . . . ?
C8 C12 C19 C14 179.90(19) . . . . ?
C13 C12 C19 C18 179.1(3) . . . . ?
C8 C12 C19 C18 -0.6(4) . . . . ?
C12 C13 N1 C14 0.2(3) . . . . ?
C19 C14 N1 C13 -0.5(2) . . . . ?
C15 C14 N1 C13 -180.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 N2 0.93 2.59 3.392(3) 145.1 . yes
C13 H13 O1 0.93 2.60 3.134(3) 116.6 1_565 yes
N1 H1A N2 0.92(3) 2.12(3) 3.012(3) 164(2) 3_676 yes

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041



