# 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_BSL_05_280
_audit_block_doi                 10.5517/ccdc.csd.cc1p52pm
_database_code_depnum_ccdc_archive 'CCDC 1554020'
loop_
_audit_author_name
_audit_author_address
'CHAYAN KUNDU'
;IISER BHOPAL
India
;
_audit_update_record             
;
2025-08-26 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38

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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0392(3)
_cell_length_b                   5.64820(10)
_cell_length_c                   20.2067(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.4100(10)
_cell_angle_gamma                90
_cell_volume                     1713.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3319
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.55

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18181
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         30.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4996
_reflns_number_gt                3385
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0463P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0125(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4996
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_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 0.24071(6) 0.35643(17) 0.72681(4) 0.0223(2) Uani 1 1 d . . . . .
O3 O 0.09853(6) 0.21560(18) 0.66290(5) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.01229(6) 0.51014(19) 0.69926(5) 0.0330(3) Uani 1 1 d . . . . .
N1 N 0.36031(7) 0.6270(2) 0.71566(5) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.31195(8) 0.4302(2) 0.69322(7) 0.0191(3) Uani 1 1 d . . . . .
C7 C 0.34991(9) 0.3187(2) 0.64276(7) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.42975(8) 0.4527(2) 0.63157(6) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.43464(8) 0.6415(2) 0.67720(6) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.26647(8) 0.1798(2) 0.53789(7) 0.0200(3) Uani 1 1 d . . . . .
C19 C 0.16826(8) 0.5117(3) 0.72692(7) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.33823(9) 0.7878(3) 0.76388(6) 0.0227(3) Uani 1 1 d . . . . .
H16 H 0.384566 0.873558 0.784875 0.027 Uiso 1 1 calc R U . . .
C8 C 0.31349(9) 0.1132(2) 0.60374(7) 0.0237(3) Uani 1 1 d . . . . .
H8A H 0.271894 0.028898 0.630078 0.028 Uiso 1 1 calc R U . . .
H8B H 0.361969 0.005895 0.595532 0.028 Uiso 1 1 calc R U . . .
C2 C 0.50234(9) 0.8069(3) 0.67893(7) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.503564 0.932748 0.708662 0.029 Uiso 1 1 calc R U . . .
C5 C 0.49728(9) 0.4278(3) 0.58750(7) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.496052 0.303749 0.557194 0.030 Uiso 1 1 calc R U . . .
C17 C 0.25586(9) 0.8301(3) 0.78282(7) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.250592 0.938865 0.816920 0.029 Uiso 1 1 calc R U . . .
C20 C 0.08404(9) 0.4154(3) 0.69602(7) 0.0242(3) Uani 1 1 d . . . . .
C14 C 0.21928(9) 0.3893(3) 0.52987(7) 0.0264(3) Uani 1 1 d . . . . .
H14 H 0.219910 0.497360 0.564625 0.032 Uiso 1 1 calc R U . . .
C18 C 0.17461(9) 0.7239(3) 0.75559(7) 0.0247(3) Uani 1 1 d . . . . .
H18 H 0.122355 0.810506 0.758248 0.030 Uiso 1 1 calc R U . . .
C10 C 0.26564(9) 0.0245(3) 0.48460(7) 0.0276(4) Uani 1 1 d . . . . .
H10 H 0.297952 -0.115710 0.488392 0.033 Uiso 1 1 calc R U . . .
C4 C 0.56599(9) 0.5908(3) 0.58973(7) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.611426 0.575221 0.560764 0.034 Uiso 1 1 calc R U . . .
C3 C 0.56825(9) 0.7781(3) 0.63470(7) 0.0272(4) Uani 1 1 d . . . . .
H3 H 0.615009 0.885941 0.634966 0.033 Uiso 1 1 calc R U . . .
C12 C 0.16997(10) 0.2835(3) 0.41889(8) 0.0347(4) Uani 1 1 d . . . . .
H12 H 0.137495 0.317303 0.379418 0.042 Uiso 1 1 calc R U . . .
C22 C 0.05713(10) -0.0731(3) 0.58190(7) 0.0342(4) Uani 1 1 d . . . . .
H22A H 0.090574 0.006949 0.549631 0.051 Uiso 1 1 calc R U . . .
H22B H 0.008428 -0.157100 0.559833 0.051 Uiso 1 1 calc R U . . .
H22C H 0.095134 -0.183018 0.606294 0.051 Uiso 1 1 calc R U . . .
C11 C 0.21719(10) 0.0758(3) 0.42570(7) 0.0350(4) Uani 1 1 d . . . . .
H11 H 0.216709 -0.031009 0.390656 0.042 Uiso 1 1 calc R U . . .
C13 C 0.17104(10) 0.4413(3) 0.47095(8) 0.0333(4) Uani 1 1 d . . . . .
H13 H 0.139458 0.582581 0.466609 0.040 Uiso 1 1 calc R U . . .
C21 C 0.02178(10) 0.1039(3) 0.62844(8) 0.0352(4) Uani 1 1 d . . . . .
H21A H -0.014156 0.221279 0.604154 0.042 Uiso 1 1 calc R U . . .
H21B H -0.014878 0.026336 0.659871 0.042 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 C15 1.3669(14) . ?
O1 C19 1.3988(15) . ?
O3 C20 1.3366(17) . ?
O3 C21 1.4559(17) . ?
O2 C20 1.2097(15) . ?
N1 C16 1.3867(16) . ?
N1 C15 1.3898(17) . ?
N1 C1 1.4012(15) . ?
C15 C7 1.3533(17) . ?
C7 C6 1.4484(18) . ?
C7 C8 1.4891(19) . ?
C6 C5 1.3971(17) . ?
C6 C1 1.4089(18) . ?
C1 C2 1.3809(18) . ?
C9 C14 1.3847(19) . ?
C9 C10 1.3882(19) . ?
C9 C8 1.5166(19) . ?
C19 C18 1.3321(19) . ?
C19 C20 1.482(2) . ?
C16 C17 1.3397(17) . ?
C16 H16 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C3 1.3833(18) . ?
C2 H2 0.9300 . ?
C5 C4 1.383(2) . ?
C5 H5 0.9300 . ?
C17 C18 1.4406(19) . ?
C17 H17 0.9300 . ?
C14 C13 1.388(2) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C4 C3 1.394(2) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C12 C11 1.374(2) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C22 C21 1.492(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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
C15 O1 C19 116.31(10) . . ?
C20 O3 C21 117.20(11) . . ?
C16 N1 C15 127.63(11) . . ?
C16 N1 C1 125.73(11) . . ?
C15 N1 C1 106.55(10) . . ?
C7 C15 O1 127.62(13) . . ?
C7 C15 N1 112.46(11) . . ?
O1 C15 N1 119.49(11) . . ?
C15 C7 C6 105.38(12) . . ?
C15 C7 C8 127.11(12) . . ?
C6 C7 C8 127.35(12) . . ?
C5 C6 C1 118.79(12) . . ?
C5 C6 C7 133.46(13) . . ?
C1 C6 C7 107.74(11) . . ?
C2 C1 N1 129.54(12) . . ?
C2 C1 C6 122.59(12) . . ?
N1 C1 C6 107.86(11) . . ?
C14 C9 C10 117.92(14) . . ?
C14 C9 C8 121.57(12) . . ?
C10 C9 C8 120.41(13) . . ?
C18 C19 O1 121.94(13) . . ?
C18 C19 C20 123.42(13) . . ?
O1 C19 C20 114.55(12) . . ?
C17 C16 N1 125.57(13) . . ?
C17 C16 H16 117.2 . . ?
N1 C16 H16 117.2 . . ?
C7 C8 C9 114.15(12) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C1 C2 C3 117.36(13) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C5 C6 118.85(13) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C16 C17 C18 126.47(13) . . ?
C16 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
O2 C20 O3 124.97(14) . . ?
O2 C20 C19 123.89(14) . . ?
O3 C20 C19 111.11(12) . . ?
C9 C14 C13 121.28(14) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C19 C18 C17 125.31(13) . . ?
C19 C18 H18 117.3 . . ?
C17 C18 H18 117.3 . . ?
C9 C10 C11 120.87(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C5 C4 C3 121.06(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 121.33(13) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C11 C12 C13 119.56(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C11 C10 120.38(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 C13 C14 119.97(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
O3 C21 C22 106.84(12) . . ?
O3 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
O3 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_F1_a
_audit_block_doi                 10.5517/ccdc.csd.cc2ptg66
_database_code_depnum_ccdc_archive 'CCDC 2497118'
loop_
_audit_author_name
_audit_author_address
'Chayan Kumar Kundu'
;IISER Bhopal
India
;
_audit_update_record             
;
2025-10-22 deposited with the CCDC.	2026-01-27 downloaded from the CCDC.
;
_audit_creation_date             2025-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         274.342
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        Pbca
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   9.2002(4)
_cell_length_b                   8.2262(3)
_cell_length_c                   37.1993(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2815.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      4.31
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7138
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.9573.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176.770
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.9771
_diffrn_reflns_Laue_measured_fraction_max 0.9820
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            64808
_diffrn_reflns_point_group_measured_fraction_full 0.9771
_diffrn_reflns_point_group_measured_fraction_max 0.9820
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         3.71
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9771
_diffrn_measured_fraction_theta_max 0.9820
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              48
_reflns_limit_l_min              0
_reflns_number_gt                3059
_reflns_number_total             3325
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3223
_refine_diff_density_min         -0.2770
_refine_diff_density_rms         0.0402
_refine_ls_d_res_high            0.7582
_refine_ls_d_res_low             5.4969
_refine_ls_goodness_of_fit_ref   0.9387
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      0.9387
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.3620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1108
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00k)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b), C00D(H00f,H00g), C00F(H00i,H00j), C00J(H00o,H00p)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00c), C00B(H00d), C00C(H00e), C00E(H00h)
2.d Idealised Me refined as rotating group:
 C00I(H00l,H00m,H00n), C00K(H00q,H00r,H00s)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O001 O 0.29788(8) 0.58772(9) 0.61413(2) 0.02115(18) Uani 1.000000 .
O002 O 0.14913(10) 0.49920(12) 0.55533(2) 0.0344(2) Uani 1.000000 .
O003 O 0.02342(10) 0.73401(12) 0.55589(2) 0.0358(2) Uani 1.000000 .
N004 N 0.35644(9) 0.68349(10) 0.67247(2) 0.01877(19) Uani 1.000000 .
C005 C 0.39332(11) 0.66174(12) 0.63671(3) 0.0191(2) Uani 1.000000 .
C006 C 0.58228(11) 0.78311(12) 0.66284(3) 0.0201(2) Uani 1.000000 .
C007 C 0.47289(10) 0.75854(12) 0.68912(3) 0.0183(2) Uani 1.000000 .
C008 C 0.52982(11) 0.71789(13) 0.62947(3) 0.0213(2) Uani 1.000000 .
C009 C 0.21704(10) 0.63939(12) 0.68832(3) 0.0198(2) Uani 1.000000 .
H00a H 0.20342(10) 0.52044(12) 0.68607(3) 0.0237(3) Uiso 1.000000 R
H00b H 0.21900(10) 0.66608(12) 0.71427(3) 0.0237(3) Uiso 1.000000 R
C00A C 0.48818(11) 0.81200(12) 0.72450(3) 0.0211(2) Uani 1.000000 .
H00c H 0.41587(11) 0.79043(12) 0.74209(3) 0.0253(3) Uiso 1.000000 R
C00B C 0.70708(11) 0.87147(13) 0.67231(3) 0.0242(2) Uani 1.000000 .
H00d H 0.78126(11) 0.89110(13) 0.65508(3) 0.0290(3) Uiso 1.000000 R
C00C C 0.61344(12) 0.89804(13) 0.73294(3) 0.0243(2) Uani 1.000000 .
H00e H 0.62676(12) 0.93638(13) 0.75681(3) 0.0292(3) Uiso 1.000000 R
C00D C 0.05183(11) 0.66607(13) 0.63310(3) 0.0227(2) Uani 1.000000 .
H00f H 0.02587(11) 0.54943(13) 0.63440(3) 0.0272(3) Uiso 1.000000 R
H00g H -0.03505(11) 0.72555(13) 0.62452(3) 0.0272(3) Uiso 1.000000 R
C00E C 0.72074(11) 0.92973(14) 0.70711(3) 0.0260(2) Uani 1.000000 .
H00h H 0.80380(11) 0.99188(14) 0.71354(3) 0.0312(3) Uiso 1.000000 R
C00F C 0.08794(11) 0.72518(13) 0.67102(3) 0.0215(2) Uani 1.000000 .
H00i H 0.00150(11) 0.70952(13) 0.68648(3) 0.0258(3) Uiso 1.000000 R
H00j H 0.10854(11) 0.84322(13) 0.67005(3) 0.0258(3) Uiso 1.000000 R
C00G C 0.17261(11) 0.68655(12) 0.60539(3) 0.0204(2) Uani 1.000000 .
H00k H 0.20140(11) 0.80349(12) 0.60359(3) 0.0245(3) Uiso 1.000000 R
C00H C 0.11789(12) 0.62593(14) 0.56931(3) 0.0256(2) Uani 1.000000 .
C00I C 0.60506(13) 0.71733(16) 0.59390(3) 0.0310(3) Uani 1.000000 .
H00l H 0.6925(6) 0.6495(10) 0.59535(8) 0.0465(4) Uiso 1.000000 GR
H00m H 0.5395(4) 0.6734(12) 0.57554(6) 0.0465(4) Uiso 1.000000 GR
H00n H 0.6326(10) 0.8287(2) 0.58746(13) 0.0465(4) Uiso 1.000000 GR
C00J C -0.04575(15) 0.6886(2) 0.52220(4) 0.0496(4) Uani 1.000000 .
H00o H 0.02821(15) 0.6759(2) 0.50308(4) 0.0595(5) Uiso 1.000000 R
H00p H -0.09805(15) 0.5842(2) 0.52498(4) 0.0595(5) Uiso 1.000000 R
C00K C -0.1497(2) 0.8206(3) 0.51260(5) 0.0787(8) Uani 1.000000 .
H00q H -0.1935(15) 0.7971(12) 0.4892(2) 0.1181(12) Uiso 1.000000 GR
H00r H -0.2261(12) 0.8271(16) 0.5309(3) 0.1181(12) Uiso 1.000000 GR
H00s H -0.0977(4) 0.9245(5) 0.5114(5) 0.1181(12) Uiso 1.000000 GR


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
O001 C005 1.3591(12) . ?
O001 C00G 1.4473(12) . ?
O002 C00H 1.2000(15) . ?
O003 C00H 1.3398(14) . ?
O003 C00J 1.4544(16) . ?
N004 C005 1.3845(13) . ?
N004 C007 1.3830(13) . ?
N004 C009 1.4574(12) . ?
C005 C008 1.3649(14) . ?
C006 C007 1.4177(14) . ?
C006 C008 1.4358(15) . ?
C006 C00B 1.4039(15) . ?
C007 C00A 1.3946(14) . ?
C008 C00I 1.4934(15) . ?
C009 H00a 0.9900 . ?
C009 H00b 0.9900 . ?
C009 C00F 1.5242(14) . ?
C00A H00c 0.9500 . ?
C00A C00C 1.3884(15) . ?
C00B H00d 0.9500 . ?
C00B C00E 1.3863(16) . ?
C00C H00e 0.9500 . ?
C00C C00E 1.4020(16) . ?
C00D H00f 0.9900 . ?
C00D H00g 0.9900 . ?
C00D C00F 1.5283(14) . ?
C00D C00G 1.5251(14) . ?
C00E H00h 0.9500 . ?
C00F H00i 0.9900 . ?
C00F H00j 0.9900 . ?
C00G H00k 1.0000 . ?
C00G C00H 1.5177(15) . ?
C00I H00l 0.9800 . ?
C00I H00m 0.9800 . ?
C00I H00n 0.9800 . ?
C00J H00o 0.9900 . ?
C00J H00p 0.9900 . ?
C00J C00K 1.490(2) . ?
C00K H00q 0.9800 . ?
C00K H00r 0.9800 . ?
C00K H00s 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
C00G O001 C005 113.68(8) . . ?
C00J O003 C00H 115.75(11) . . ?
C007 N004 C005 107.35(8) . . ?
C009 N004 C005 124.91(9) . . ?
C009 N004 C007 127.70(9) . . ?
N004 C005 O001 119.56(9) . . ?
C008 C005 O001 128.62(10) . . ?
C008 C005 N004 111.79(9) . . ?
C008 C006 C007 107.72(9) . . ?
C00B C006 C007 118.78(10) . . ?
C00B C006 C008 133.26(10) . . ?
C006 C007 N004 107.74(9) . . ?
C00A C007 N004 129.91(9) . . ?
C00A C007 C006 122.29(9) . . ?
C006 C008 C005 105.38(9) . . ?
C00I C008 C005 126.88(10) . . ?
C00I C008 C006 127.69(10) . . ?
H00a C009 N004 108.86(5) . . ?
H00b C009 N004 108.86(5) . . ?
H00b C009 H00a 107.7 . . ?
C00F C009 N004 113.55(8) . . ?
C00F C009 H00a 108.86(5) . . ?
C00F C009 H00b 108.86(6) . . ?
H00c C00A C007 121.37(6) . . ?
C00C C00A C007 117.26(10) . . ?
C00C C00A H00c 121.37(6) . . ?
H00d C00B C006 120.41(6) . . ?
C00E C00B C006 119.18(10) . . ?
C00E C00B H00d 120.41(6) . . ?
H00e C00C C00A 119.19(6) . . ?
C00E C00C C00A 121.61(10) . . ?
C00E C00C H00e 119.19(6) . . ?
H00g C00D H00f 107.5 . . ?
C00F C00D H00f 108.41(6) . . ?
C00F C00D H00g 108.41(6) . . ?
C00G C00D H00f 108.41(6) . . ?
C00G C00D H00g 108.41(6) . . ?
C00G C00D C00F 115.48(8) . . ?
C00C C00E C00B 120.79(10) . . ?
H00h C00E C00B 119.60(6) . . ?
H00h C00E C00C 119.60(6) . . ?
C00D C00F C009 114.32(9) . . ?
H00i C00F C009 108.68(5) . . ?
H00i C00F C00D 108.68(5) . . ?
H00j C00F C009 108.68(5) . . ?
H00j C00F C00D 108.68(6) . . ?
H00j C00F H00i 107.6 . . ?
C00D C00G O001 111.49(8) . . ?
H00k C00G O001 110.16(5) . . ?
H00k C00G C00D 110.16(6) . . ?
C00H C00G O001 106.15(8) . . ?
C00H C00G C00D 108.64(8) . . ?
C00H C00G H00k 110.16(6) . . ?
O003 C00H O002 124.78(11) . . ?
C00G C00H O002 126.10(10) . . ?
C00G C00H O003 109.07(10) . . ?
H00l C00I C008 109.5 . . ?
H00m C00I C008 109.5 . . ?
H00m C00I H00l 109.5 . . ?
H00n C00I C008 109.5 . . ?
H00n C00I H00l 109.5 . . ?
H00n C00I H00m 109.5 . . ?
H00o C00J O003 110.22(7) . . ?
H00p C00J O003 110.22(8) . . ?
H00p C00J H00o 108.5 . . ?
C00K C00J O003 107.45(15) . . ?
C00K C00J H00o 110.22(9) . . ?
C00K C00J H00p 110.22(12) . . ?
H00q C00K C00J 109.5 . . ?
H00r C00K C00J 109.5 . . ?
H00r C00K H00q 109.5 . . ?
H00s C00K C00J 109.5 . . ?
H00s C00K H00q 109.5 . . ?
H00s C00K H00r 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
O001 C005 N004 C007 179.07(9) . . . . ?
O001 C005 N004 C009 -3.06(11) . . . . ?
O001 C005 C008 C006 -179.45(11) . . . . ?
O001 C005 C008 C00I 2.89(14) . . . . ?
O001 C00G C00D C00F 64.68(9) . . . . ?
O001 C00G C00H O002 16.18(10) . . . . ?
O001 C00G C00H O003 -166.32(8) . . . . ?
O002 C00H O003 C00J 1.08(14) . . . . ?
O002 C00H C00G C00D -103.84(12) . . . . ?
O003 C00H C00G C00D 73.66(9) . . . . ?
N004 C005 O001 C00G 71.70(10) . . . . ?
N004 C005 C008 C006 -1.27(9) . . . . ?
N004 C005 C008 C00I -178.94(9) . . . . ?
N004 C007 C006 C008 -0.95(9) . . . . ?
N004 C007 C006 C00B 174.12(8) . . . . ?
N004 C007 C00A C00C -173.92(11) . . . . ?
N004 C009 C00F C00D 71.33(9) . . . . ?
C005 O001 C00G C00D -87.00(9) . . . . ?
C005 O001 C00G C00H 154.85(9) . . . . ?
C005 N004 C007 C006 0.18(9) . . . . ?
C005 N004 C007 C00A 177.32(8) . . . . ?
C005 N004 C009 C00F -59.32(10) . . . . ?
C005 C008 C006 C007 1.34(9) . . . . ?
C005 C008 C006 C00B -172.72(8) . . . . ?
C006 C007 N004 C009 -177.61(7) . . . . ?
C006 C007 C00A C00C 2.85(11) . . . . ?
C006 C00B C00E C00C 1.53(12) . . . . ?
C007 N004 C005 C008 0.71(9) . . . . ?
C007 N004 C009 C00F 118.12(10) . . . . ?
C007 C006 C008 C00I 178.98(8) . . . . ?
C007 C006 C00B C00E 1.01(11) . . . . ?
C007 C00A C00C C00E -0.22(11) . . . . ?
C008 C005 O001 C00G -110.25(11) . . . . ?
C008 C005 N004 C009 178.58(8) . . . . ?
C008 C006 C007 C00A -178.35(8) . . . . ?
C008 C006 C00B C00E 174.55(12) . . . . ?
C009 N004 C007 C00A -0.47(12) . . . . ?
C009 C00F C00D C00G -60.24(9) . . . . ?
C00A C007 C006 C00B -3.28(11) . . . . ?
C00A C00C C00E C00B -1.97(12) . . . . ?
C00B C006 C008 C00I 4.92(15) . . . . ?
C00F C00D C00G C00H -178.68(9) . . . . ?
C00G C00H O003 C00J -176.46(10) . . . . ?
C00H O003 C00J C00K 177.99(13) . . . . ?


_olex2_exptl_crystal_mounting_method Lalit
_olex2_submission_special_instructions 'No special instructions were received'
