# 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. 
# 
#######################################################################

data_RKP_RB_644_1613_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2513848'
loop_
_audit_author_name
_audit_author_address
'RAJNISH BUDHWAN' 'IIT Roorkee'
_audit_update_record             
;
2026-02-19 deposited with the CCDC.	2026-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O5'
_chemical_formula_sum            'C19 H13 N O5'
_chemical_formula_weight         335.30

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                   12.7597(5)
_cell_length_b                   6.7156(2)
_cell_length_c                   17.4401(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.4980(10)
_cell_angle_gamma                90
_cell_volume                     1487.55(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    104(2)
_cell_measurement_reflns_used    9785
_cell_measurement_theta_min      3.2525
_cell_measurement_theta_max      28.2810

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   0.78
_exptl_transmission_factor_max   0.98
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      104(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST photon III C7'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24150
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         25.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2728
_reflns_number_gt                2515
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0564P)²+0.4545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.69943(6) 0.27767(12) 0.64467(4) 0.0165(2) Uani 1 1 d . . . . .
O2 O 0.68079(7) 0.19303(12) 0.48252(4) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.34479(6) 0.39160(15) 0.63496(5) 0.0256(2) Uani 1 1 d . . . . .
O4 O 0.42809(6) 0.07748(12) 0.75771(4) 0.0198(2) Uani 1 1 d . . . . .
O5 O 0.48494(6) 0.76026(13) 0.93428(4) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.67404(8) 0.31670(14) 0.72111(5) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.40689(9) 0.28677(16) 0.51720(6) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.30653(9) 0.28945(17) 0.47828(7) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.247683 0.323514 0.505120 0.022 Uiso 1 1 calc R U . . .
C3 C 0.29181(10) 0.24265(17) 0.40048(7) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.222973 0.244127 0.374360 0.025 Uiso 1 1 calc R U . . .
C4 C 0.37758(10) 0.19362(17) 0.36065(7) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.367232 0.161169 0.307448 0.025 Uiso 1 1 calc R U . . .
C5 C 0.47819(10) 0.19208(16) 0.39858(6) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.536650 0.159530 0.371091 0.022 Uiso 1 1 calc R U . . .
C6 C 0.49408(9) 0.23801(15) 0.47679(6) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.60382(9) 0.23321(16) 0.51544(6) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.60919(9) 0.27817(16) 0.59870(6) 0.0142(2) Uani 1 1 d . . . . .
C9 C 0.52615(9) 0.31654(16) 0.63902(6) 0.0144(2) Uani 1 1 d . . . . .
C10 C 0.41859(9) 0.33591(17) 0.60143(6) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.57155(9) 0.33885(16) 0.71661(6) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.51580(9) 0.37868(17) 0.78559(6) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.43758(9) 0.24466(17) 0.80285(6) 0.0164(2) Uani 1 1 d . . . . .
C14 C 0.37823(9) 0.28572(18) 0.86399(6) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.325070 0.195605 0.876532 0.023 Uiso 1 1 calc R U . . .
C15 C 0.39712(9) 0.45858(18) 0.90640(6) 0.0190(3) Uani 1 1 d . . . . .
H15 H 0.355715 0.487119 0.947510 0.023 Uiso 1 1 calc R U . . .
C16 C 0.47562(9) 0.59108(17) 0.88986(6) 0.0180(3) Uani 1 1 d . . . . .
C17 C 0.53644(9) 0.55013(17) 0.82964(6) 0.0165(2) Uani 1 1 d . . . . .
H17 H 0.591414 0.637971 0.818654 0.020 Uiso 1 1 calc R U . . .
C18 C 0.33822(10) -0.04626(19) 0.76508(7) 0.0238(3) Uani 1 1 d . . . . .
H18A H 0.273855 0.032753 0.754696 0.036 Uiso 1 1 calc R U . . .
H18B H 0.341622 -0.100052 0.817493 0.036 Uiso 1 1 calc R U . . .
H18C H 0.337679 -0.156189 0.728083 0.036 Uiso 1 1 calc R U . . .
C19 C 0.57398(10) 0.88459(19) 0.92560(7) 0.0225(3) Uani 1 1 d . . . . .
H19A H 0.571554 0.930997 0.872183 0.034 Uiso 1 1 calc R U . . .
H19B H 0.638827 0.808537 0.938513 0.034 Uiso 1 1 calc R U . . .
H19C H 0.572610 0.999447 0.960149 0.034 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 C8 1.3385(14) . ?
O1 N1 1.4261(11) . ?
O2 C7 1.2145(14) . ?
O3 C10 1.2141(14) . ?
O4 C13 1.3698(14) . ?
O4 C18 1.4319(14) . ?
O5 C16 1.3738(14) . ?
O5 C19 1.4297(15) . ?
N1 C11 1.3111(15) . ?
C1 C2 1.3908(17) . ?
C1 C6 1.4113(16) . ?
C1 C10 1.4991(15) . ?
C2 C3 1.3879(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3907(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3867(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3943(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4950(17) . ?
C7 C8 1.4783(15) . ?
C8 C9 1.3515(15) . ?
C9 C11 1.4279(15) . ?
C9 C10 1.4689(16) . ?
C11 C12 1.4794(15) . ?
C12 C17 1.3952(16) . ?
C12 C13 1.3979(16) . ?
C13 C14 1.3934(16) . ?
C14 C15 1.3851(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3905(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3918(15) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C8 O1 N1 107.46(8) . . ?
C13 O4 C18 116.85(9) . . ?
C16 O5 C19 116.74(9) . . ?
C11 N1 O1 106.23(9) . . ?
C2 C1 C6 119.49(10) . . ?
C2 C1 C10 118.42(10) . . ?
C6 C1 C10 122.08(10) . . ?
C3 C2 C1 120.41(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.18(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.03(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.41(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.48(11) . . ?
C5 C6 C7 118.58(10) . . ?
C1 C6 C7 121.94(10) . . ?
O2 C7 C8 123.10(11) . . ?
O2 C7 C6 123.82(10) . . ?
C8 C7 C6 113.06(10) . . ?
O1 C8 C9 111.17(9) . . ?
O1 C8 C7 122.96(10) . . ?
C9 C8 C7 125.82(11) . . ?
C8 C9 C11 104.24(10) . . ?
C8 C9 C10 122.02(10) . . ?
C11 C9 C10 133.67(10) . . ?
O3 C10 C9 123.16(10) . . ?
O3 C10 C1 122.05(10) . . ?
C9 C10 C1 114.77(9) . . ?
N1 C11 C9 110.89(10) . . ?
N1 C11 C12 121.77(10) . . ?
C9 C11 C12 127.34(10) . . ?
C17 C12 C13 120.91(10) . . ?
C17 C12 C11 121.12(10) . . ?
C13 C12 C11 117.87(10) . . ?
O4 C13 C14 125.26(11) . . ?
O4 C13 C12 115.44(10) . . ?
C14 C13 C12 119.27(11) . . ?
C15 C14 C13 119.66(11) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.17(10) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
O5 C16 C15 115.94(10) . . ?
O5 C16 C17 124.37(11) . . ?
C15 C16 C17 119.66(11) . . ?
C16 C17 C12 119.28(11) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 O1 N1 C11 -0.25(11) . . . . ?
C6 C1 C2 C3 0.65(17) . . . . ?
C10 C1 C2 C3 -179.24(10) . . . . ?
C1 C2 C3 C4 -0.33(18) . . . . ?
C2 C3 C4 C5 -0.24(17) . . . . ?
C3 C4 C5 C6 0.49(17) . . . . ?
C4 C5 C6 C1 -0.18(16) . . . . ?
C4 C5 C6 C7 179.61(10) . . . . ?
C2 C1 C6 C5 -0.39(16) . . . . ?
C10 C1 C6 C5 179.49(10) . . . . ?
C2 C1 C6 C7 179.83(10) . . . . ?
C10 C1 C6 C7 -0.29(16) . . . . ?
C5 C6 C7 O2 0.63(17) . . . . ?
C1 C6 C7 O2 -179.59(10) . . . . ?
C5 C6 C7 C8 -178.08(9) . . . . ?
C1 C6 C7 C8 1.71(15) . . . . ?
N1 O1 C8 C9 0.58(12) . . . . ?
N1 O1 C8 C7 -176.97(10) . . . . ?
O2 C7 C8 O1 -0.20(17) . . . . ?
C6 C7 C8 O1 178.52(9) . . . . ?
O2 C7 C8 C9 -177.38(11) . . . . ?
C6 C7 C8 C9 1.33(16) . . . . ?
O1 C8 C9 C11 -0.66(12) . . . . ?
C7 C8 C9 C11 176.81(10) . . . . ?
O1 C8 C9 C10 176.71(9) . . . . ?
C7 C8 C9 C10 -5.82(18) . . . . ?
C8 C9 C10 O3 -171.66(11) . . . . ?
C11 C9 C10 O3 4.8(2) . . . . ?
C8 C9 C10 C1 6.73(15) . . . . ?
C11 C9 C10 C1 -176.80(11) . . . . ?
C2 C1 C10 O3 -5.48(17) . . . . ?
C6 C1 C10 O3 174.63(11) . . . . ?
C2 C1 C10 C9 176.11(10) . . . . ?
C6 C1 C10 C9 -3.77(15) . . . . ?
O1 N1 C11 C9 -0.16(12) . . . . ?
O1 N1 C11 C12 179.07(9) . . . . ?
C8 C9 C11 N1 0.50(13) . . . . ?
C10 C9 C11 N1 -176.41(11) . . . . ?
C8 C9 C11 C12 -178.67(11) . . . . ?
C10 C9 C11 C12 4.4(2) . . . . ?
N1 C11 C12 C17 61.61(15) . . . . ?
C9 C11 C12 C17 -119.29(13) . . . . ?
N1 C11 C12 C13 -121.84(12) . . . . ?
C9 C11 C12 C13 57.25(16) . . . . ?
C18 O4 C13 C14 11.76(16) . . . . ?
C18 O4 C13 C12 -169.96(10) . . . . ?
C17 C12 C13 O4 -177.07(10) . . . . ?
C11 C12 C13 O4 6.38(15) . . . . ?
C17 C12 C13 C14 1.32(17) . . . . ?
C11 C12 C13 C14 -175.23(10) . . . . ?
O4 C13 C14 C15 178.55(10) . . . . ?
C12 C13 C14 C15 0.33(17) . . . . ?
C13 C14 C15 C16 -1.02(17) . . . . ?
C19 O5 C16 C15 171.58(10) . . . . ?
C19 O5 C16 C17 -10.50(16) . . . . ?
C14 C15 C16 O5 178.10(10) . . . . ?
C14 C15 C16 C17 0.07(17) . . . . ?
O5 C16 C17 C12 -176.29(10) . . . . ?
C15 C16 C17 C12 1.55(16) . . . . ?
C13 C12 C17 C16 -2.26(16) . . . . ?
C11 C12 C17 C16 174.18(10) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_rkp_rb_840_2073_a
_database_code_depnum_ccdc_archive 'CCDC 2513849'
loop_
_audit_author_name
_audit_author_address
'RAJNISH BUDHWAN'
;IIT Roorkee
India
;
_audit_update_record             
;
2026-02-19 deposited with the CCDC.	2026-03-03 downloaded from the CCDC.
;
_audit_creation_date             2026-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 N O4'
_chemical_formula_sum            'C24 H15 N O4'
_chemical_formula_weight         381.37
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.684(3)
_cell_length_b                   13.176(6)
_cell_length_c                   19.701(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1735.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5371
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      24.759
_cell_measurement_theta_min      2.582
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7327
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1730 before and 0.0927 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21461
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.095
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_min         2.067
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2689
_reflns_number_total             3050
_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 V8.42 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.42 (?, 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         0.171
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.081
_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)+(0.0514P)²+0.3189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C21(H21), C22(H22), C23(H23), C24(H24)
;
_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
C1 C 1.1887(5) 0.5827(3) 0.39993(16) 0.0210(8) Uani 1 1 d . . . . .
C2 C 1.2581(5) 0.6749(3) 0.42463(17) 0.0242(8) Uani 1 1 d . . . . .
H2 H 1.185829 0.735353 0.415249 0.029 Uiso 1 1 calc R U . . .
C3 C 1.4321(5) 0.6795(3) 0.46286(17) 0.0275(8) Uani 1 1 d . . . . .
H3 H 1.477354 0.742950 0.479821 0.033 Uiso 1 1 calc R U . . .
C4 C 1.5401(5) 0.5925(3) 0.47646(16) 0.0258(8) Uani 1 1 d . . . . .
H4 H 1.659327 0.595973 0.502630 0.031 Uiso 1 1 calc R U . . .
C5 C 1.4734(5) 0.5004(3) 0.45170(16) 0.0244(8) Uani 1 1 d . . . . .
H5 H 1.547091 0.440158 0.460607 0.029 Uiso 1 1 calc R U . . .
C6 C 1.2991(5) 0.4959(3) 0.41392(16) 0.0230(8) Uani 1 1 d . . . . .
H6 H 1.254154 0.432266 0.397209 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9953(5) 0.5737(3) 0.36161(17) 0.0236(8) Uani 1 1 d . . . . .
H7A H 1.004605 0.518257 0.327873 0.028 Uiso 1 1 calc R U . . .
H7B H 0.884844 0.557777 0.393360 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7792(5) 0.6760(3) 0.29344(17) 0.0211(7) Uani 1 1 d . . . . .
C9 C 0.6362(5) 0.6007(3) 0.28819(18) 0.0236(8) Uani 1 1 d . . . . .
H9 H 0.655458 0.537666 0.310616 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4640(5) 0.6172(2) 0.25016(16) 0.0237(8) Uani 1 1 d . . . . .
H10 H 0.366055 0.565093 0.247269 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4325(5) 0.7081(2) 0.21635(16) 0.0202(7) Uani 1 1 d . . . . .
C12 C 0.5776(5) 0.7841(3) 0.22322(17) 0.0233(8) Uani 1 1 d . . . . .
H12 H 0.557778 0.847575 0.201326 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7486(5) 0.7688(2) 0.26108(16) 0.0237(8) Uani 1 1 d . . . . .
H13 H 0.845143 0.821399 0.265093 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2557(5) 0.7269(2) 0.17310(16) 0.0201(7) Uani 1 1 d . . . . .
C15 C 0.0900(5) 0.6641(2) 0.15105(16) 0.0199(7) Uani 1 1 d . . . . .
C16 C -0.0161(5) 0.7252(2) 0.10872(16) 0.0202(7) Uani 1 1 d . . . . .
C17 C 0.0116(5) 0.5616(2) 0.16559(16) 0.0202(8) Uani 1 1 d . . . . .
C18 C -0.2029(5) 0.7019(2) 0.07211(17) 0.0210(7) Uani 1 1 d . . . . .
C19 C -0.2844(5) 0.6006(2) 0.08802(16) 0.0204(8) Uani 1 1 d . . . . .
C20 C -0.1840(5) 0.5352(3) 0.13279(17) 0.0211(8) Uani 1 1 d . . . . .
C21 C -0.4674(5) 0.5712(3) 0.05883(16) 0.0219(8) Uani 1 1 d . . . . .
H21 H -0.534099 0.614967 0.027874 0.026 Uiso 1 1 calc R U . . .
C22 C -0.5491(5) 0.4786(3) 0.07547(16) 0.0247(8) Uani 1 1 d . . . . .
H22 H -0.673007 0.458620 0.055998 0.030 Uiso 1 1 calc R U . . .
C23 C -0.4525(5) 0.4145(3) 0.12024(16) 0.0244(8) Uani 1 1 d . . . . .
H23 H -0.511537 0.351233 0.131777 0.029 Uiso 1 1 calc R U . . .
C24 C -0.2696(5) 0.4418(2) 0.14861(16) 0.0218(8) Uani 1 1 d . . . . .
H24 H -0.203163 0.396727 0.178755 0.026 Uiso 1 1 calc R U . . .
N1 N 0.2404(4) 0.8178(2) 0.14536(14) 0.0242(7) Uani 1 1 d . . . . .
O1 O 0.9561(3) 0.66797(17) 0.32793(11) 0.0254(6) Uani 1 1 d . . . . .
O2 O 0.0667(3) 0.81723(17) 0.10417(11) 0.0250(6) Uani 1 1 d . . . . .
O3 O 0.0949(4) 0.50125(16) 0.20325(12) 0.0266(6) Uani 1 1 d . . . . .
O4 O -0.2813(4) 0.76226(18) 0.03357(12) 0.0283(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(5) . ?
C1 C6 1.388(5) . ?
C1 C7 1.502(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 O1 1.432(4) . ?
C8 C9 1.382(5) . ?
C8 C13 1.394(5) . ?
C8 O1 1.368(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 C12 1.401(5) . ?
C11 C14 1.478(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.449(5) . ?
C14 N1 1.321(4) . ?
C15 C16 1.359(4) . ?
C15 C17 1.476(5) . ?
C16 C18 1.474(4) . ?
C16 O2 1.336(4) . ?
C17 C20 1.499(5) . ?
C17 O3 1.222(4) . ?
C18 C19 1.476(5) . ?
C18 O4 1.218(4) . ?
C19 C20 1.404(5) . ?
C19 C21 1.406(5) . ?
C20 C24 1.392(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(5) . ?
C24 H24 0.9500 . ?
N1 O2 1.417(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
C2 C1 C7 122.1(3) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 119.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C7 C1 108.8(3) . . ?
O1 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C9 C8 C13 119.6(3) . . ?
O1 C8 C9 125.4(3) . . ?
O1 C8 C13 115.0(3) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 117.8(3) . . ?
C10 C11 C14 122.9(3) . . ?
C12 C11 C14 119.3(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C11 133.5(3) . . ?
N1 C14 C11 116.9(3) . . ?
N1 C14 C15 109.6(3) . . ?
C14 C15 C17 137.3(3) . . ?
C16 C15 C14 104.2(3) . . ?
C16 C15 C17 118.4(3) . . ?
C15 C16 C18 128.3(3) . . ?
O2 C16 C15 111.3(3) . . ?
O2 C16 C18 120.4(3) . . ?
C15 C17 C20 116.0(3) . . ?
O3 C17 C15 123.5(3) . . ?
O3 C17 C20 120.5(3) . . ?
C16 C18 C19 113.4(3) . . ?
O4 C18 C16 122.3(3) . . ?
O4 C18 C19 124.4(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 C21 120.3(3) . . ?
C21 C19 C18 118.9(3) . . ?
C19 C20 C17 123.0(3) . . ?
C24 C20 C17 117.9(3) . . ?
C24 C20 C19 119.1(3) . . ?
C19 C21 H21 120.3 . . ?
C22 C21 C19 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C20 C24 H24 120.0 . . ?
C23 C24 C20 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C14 N1 O2 107.2(3) . . ?
C8 O1 C7 117.1(3) . . ?
C16 O2 N1 107.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C7 O1 C8 -176.3(3) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C1 C7 O1 28.1(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C1 C7 O1 -154.6(3) . . . . ?
C7 C1 C2 C3 176.6(3) . . . . ?
C7 C1 C6 C5 -177.1(3) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
C9 C8 O1 C7 -0.3(4) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C9 C10 C11 C14 177.3(3) . . . . ?
C10 C11 C12 C13 1.4(5) . . . . ?
C10 C11 C14 C15 -4.6(5) . . . . ?
C10 C11 C14 N1 178.0(3) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
C11 C14 C15 C16 -176.6(3) . . . . ?
C11 C14 C15 C17 7.5(6) . . . . ?
C11 C14 N1 O2 177.5(2) . . . . ?
C12 C11 C14 C15 174.3(3) . . . . ?
C12 C11 C14 N1 -3.0(4) . . . . ?
C13 C8 C9 C10 0.8(5) . . . . ?
C13 C8 O1 C7 -179.5(3) . . . . ?
C14 C11 C12 C13 -177.7(3) . . . . ?
C14 C15 C16 C18 -178.9(3) . . . . ?
C14 C15 C16 O2 -0.9(4) . . . . ?
C14 C15 C17 C20 174.1(3) . . . . ?
C14 C15 C17 O3 -4.0(6) . . . . ?
C14 N1 O2 C16 -0.1(3) . . . . ?
C15 C14 N1 O2 -0.5(3) . . . . ?
C15 C16 C18 C19 3.5(5) . . . . ?
C15 C16 C18 O4 -177.5(3) . . . . ?
C15 C16 O2 N1 0.7(3) . . . . ?
C15 C17 C20 C19 3.1(4) . . . . ?
C15 C17 C20 C24 -176.0(3) . . . . ?
C16 C15 C17 C20 -1.3(4) . . . . ?
C16 C15 C17 O3 -179.5(3) . . . . ?
C16 C18 C19 C20 -1.5(4) . . . . ?
C16 C18 C19 C21 177.0(3) . . . . ?
C17 C15 C16 C18 -2.1(5) . . . . ?
C17 C15 C16 O2 175.9(3) . . . . ?
C17 C20 C24 C23 179.0(3) . . . . ?
C18 C16 O2 N1 178.8(3) . . . . ?
C18 C19 C20 C17 -1.6(5) . . . . ?
C18 C19 C20 C24 177.5(3) . . . . ?
C18 C19 C21 C22 -177.3(3) . . . . ?
C19 C20 C24 C23 -0.1(5) . . . . ?
C19 C21 C22 C23 -0.3(5) . . . . ?
C20 C19 C21 C22 1.2(5) . . . . ?
C21 C19 C20 C17 179.9(3) . . . . ?
C21 C19 C20 C24 -1.0(5) . . . . ?
C21 C22 C23 C24 -0.9(5) . . . . ?
C22 C23 C24 C20 1.1(5) . . . . ?
N1 C14 C15 C16 0.9(4) . . . . ?
N1 C14 C15 C17 -175.0(4) . . . . ?
O1 C8 C9 C10 -178.4(3) . . . . ?
O1 C8 C13 C12 178.2(3) . . . . ?
O2 C16 C18 C19 -174.3(3) . . . . ?
O2 C16 C18 O4 4.7(5) . . . . ?
O3 C17 C20 C19 -178.7(3) . . . . ?
O3 C17 C20 C24 2.3(4) . . . . ?
O4 C18 C19 C20 179.6(3) . . . . ?
O4 C18 C19 C21 -1.9(5) . . . . ?

_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_rj
_database_code_depnum_ccdc_archive 'CCDC 2513852'
loop_
_audit_author_name
_audit_author_address
'RAJNISH BUDHWAN'
;IIT Roorkee
India
;
_audit_update_record             
;
2025-12-06 deposited with the CCDC.	2026-03-03 downloaded from the CCDC.
;
_audit_creation_date             2025-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_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                   12.0197(5)
_cell_length_b                   17.7856(8)
_cell_length_c                   12.4927(6)
_cell_angle_alpha                90
_cell_angle_beta                 152.9491(10)
_cell_angle_gamma                90
_cell_volume                     1214.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5175
_cell_measurement_temperature    108.00
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46846
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.041
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_min         3.432
_diffrn_ambient_temperature      108.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1981
_reflns_number_total             2128
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.048
_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)+(0.0440P)²+0.6988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.05994(16) 0.61337(5) 0.55580(16) 0.0225(2) Uani 1 1 d . . . . .
N1 N 1.1425(2) 0.56554(6) 0.5433(2) 0.0216(3) Uani 1 1 d . . . . .
C1 C 0.7005(2) 0.67643(7) 0.3113(2) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.4854(2) 0.71407(8) 0.0988(2) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.411069 0.704809 -0.032364 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3807(3) 0.76487(8) 0.0795(2) 0.0262(3) Uani 1 1 d . . . . .
H3 H 0.235821 0.790933 -0.064294 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4865(3) 0.77787(8) 0.2695(3) 0.0274(3) Uani 1 1 d . . . . .
H4 H 0.414071 0.812691 0.255656 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6979(3) 0.73992(8) 0.4794(3) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.769798 0.748607 0.609113 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8053(2) 0.68929(8) 0.5012(2) 0.0217(3) Uani 1 1 d . . . . .
H6 H 0.950199 0.663391 0.645406 0.026 Uiso 1 1 calc R U . . .
C7 C 0.8157(2) 0.62521(7) 0.3334(2) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.7361(2) 0.58706(7) 0.1785(2) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.574060 0.584726 0.012369 0.024 Uiso 1 1 calc R U . . .
C9 C 0.9479(2) 0.55121(7) 0.3187(2) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.9671(2) 0.50364(7) 0.2386(2) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.7605(2) 0.46697(8) 0.0223(2) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.607350 0.473119 -0.074093 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7779(3) 0.42137(8) -0.0529(2) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.636086 0.396232 -0.199964 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9986(3) 0.41185(8) 0.0826(2) 0.0243(3) Uani 1 1 d . . . . .
C14 C 1.2036(3) 0.44925(8) 0.2976(2) 0.0242(3) Uani 1 1 d . . . . .
H14 H 1.356001 0.443678 0.392590 0.029 Uiso 1 1 calc R U . . .
C15 C 1.1895(2) 0.49448(8) 0.3759(2) 0.0233(3) Uani 1 1 d . . . . .
H15 H 1.331813 0.519322 0.523393 0.028 Uiso 1 1 calc R U . . .
C16 C 1.0147(3) 0.36291(9) -0.0014(3) 0.0313(4) Uani 1 1 d . . . . .
H16A H 1.169876 0.335337 0.132253 0.047 Uiso 1 1 calc R U . . .
H16B H 1.006285 0.394366 -0.072915 0.047 Uiso 1 1 calc R U . . .
H16C H 0.878339 0.327133 -0.118410 0.047 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 N1 1.4172(14) . ?
O1 C7 1.3614(16) . ?
N1 C9 1.3114(18) . ?
C1 C2 1.3982(19) . ?
C1 C6 1.3938(19) . ?
C1 C7 1.4633(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3503(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.4192(19) . ?
C9 C10 1.4762(19) . ?
C10 C11 1.3934(19) . ?
C10 C15 1.3964(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(2) . ?
C13 C14 1.393(2) . ?
C13 C16 1.503(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O1 N1 108.48(10) . . ?
C9 N1 O1 105.25(10) . . ?
C2 C1 C7 119.69(12) . . ?
C6 C1 C2 119.53(13) . . ?
C6 C1 C7 120.77(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.98(13) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.30(13) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.84(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.35(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.00(13) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 116.08(11) . . ?
C8 C7 O1 109.56(12) . . ?
C8 C7 C1 134.32(12) . . ?
C7 C8 H8 127.6 . . ?
C7 C8 C9 104.76(12) . . ?
C9 C8 H8 127.6 . . ?
N1 C9 C8 111.94(12) . . ?
N1 C9 C10 120.29(12) . . ?
C8 C9 C10 127.76(12) . . ?
C11 C10 C9 119.92(12) . . ?
C11 C10 C15 118.86(12) . . ?
C15 C10 C9 121.22(12) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.19(13) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.33(13) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 118.06(13) . . ?
C12 C13 C16 120.83(13) . . ?
C14 C13 C16 121.11(13) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.29(13) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.26(13) . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 N1 C9 C8 -0.46(14) . . . . ?
O1 N1 C9 C10 178.65(11) . . . . ?
O1 C7 C8 C9 -0.75(15) . . . . ?
N1 O1 C7 C1 -177.36(10) . . . . ?
N1 O1 C7 C8 0.51(14) . . . . ?
N1 C9 C10 C11 157.45(13) . . . . ?
N1 C9 C10 C15 -22.61(19) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C7 C8 C9 176.57(14) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C7 O1 155.73(12) . . . . ?
C2 C1 C7 C8 -21.5(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C6 C1 C7 O1 -23.03(18) . . . . ?
C6 C1 C7 C8 159.78(15) . . . . ?
C7 O1 N1 C9 -0.02(13) . . . . ?
C7 C1 C2 C3 -177.46(12) . . . . ?
C7 C1 C6 C5 177.88(12) . . . . ?
C7 C8 C9 N1 0.77(16) . . . . ?
C7 C8 C9 C10 -178.26(12) . . . . ?
C8 C9 C10 C11 -23.6(2) . . . . ?
C8 C9 C10 C15 156.35(14) . . . . ?
C9 C10 C11 C12 -179.26(12) . . . . ?
C9 C10 C15 C14 179.73(12) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 C16 -179.52(13) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C10 -0.2(2) . . . . ?
C15 C10 C11 C12 0.8(2) . . . . ?
C16 C13 C14 C15 179.99(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
