# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_HH-187_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2098054'
loop_
_audit_author_name
_audit_author_address
'Dr Babulal Das'
;IITG
India
;
_audit_update_record             
;
2021-10-09 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 N O4'
_chemical_formula_weight         453.51

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                   13.578(4)
_cell_length_b                   11.198(3)
_cell_length_c                   15.831(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.443(4)
_cell_angle_gamma                90
_cell_volume                     2399.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3013
_cell_measurement_theta_min      1.905
_cell_measurement_theta_max      24.994

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.083
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62998
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4212
_reflns_number_gt                3013
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0699P)²+0.6262P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0104(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4212
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O4 O 0.36976(11) 0.29472(13) 0.55544(9) 0.0579(4) Uani 1 1 d . . . . .
O1 O 0.27719(14) 0.63549(13) 0.59077(10) 0.0698(5) Uani 1 1 d . . . . .
H1 H 0.2422 0.6591 0.5496 0.105 Uiso 1 1 calc R U . . .
O3 O 0.19807(13) 0.61373(15) 0.43343(10) 0.0710(5) Uani 1 1 d . . . . .
O2 O 0.45835(12) 0.51442(18) 0.64633(11) 0.0800(5) Uani 1 1 d . . . . .
N1 N 0.34143(12) 0.41455(17) 0.71532(10) 0.0558(5) Uani 1 1 d . . . . .
C7 C 0.34468(14) 0.36082(18) 0.48494(12) 0.0469(5) Uani 1 1 d . . . . .
C14 C 0.29954(15) 0.46488(17) 0.49867(12) 0.0461(5) Uani 1 1 d . . . . .
C13 C 0.25485(16) 0.52958(19) 0.42557(13) 0.0516(5) Uani 1 1 d . . . . .
C17 C 0.20217(15) 0.44639(19) 0.62770(13) 0.0495(5) Uani 1 1 d . . . . .
C15 C 0.28487(15) 0.50905(18) 0.58768(12) 0.0492(5) Uani 1 1 d . . . . .
C22 C 0.23915(15) 0.39129(19) 0.70156(13) 0.0499(5) Uani 1 1 d . . . . .
C1 C 0.44944(15) 0.21574(19) 0.56146(13) 0.0518(5) Uani 1 1 d . . . . .
C9 C 0.28588(16) 0.35520(19) 0.33002(12) 0.0526(5) Uani 1 1 d . . . . .
C16 C 0.37407(16) 0.4798(2) 0.65122(13) 0.0564(6) Uani 1 1 d . . . . .
C25 C 0.38688(15) 0.4142(2) 0.86984(13) 0.0543(5) Uani 1 1 d . . . . .
C8 C 0.36037(16) 0.30967(19) 0.40033(13) 0.0531(5) Uani 1 1 d . . . . .
H8A H 0.3556 0.2234 0.4034 0.064 Uiso 1 1 calc R U . . .
H8B H 0.4266 0.3294 0.3859 0.064 Uiso 1 1 calc R U . . .
C12 C 0.27991(17) 0.4904(2) 0.33942(13) 0.0564(6) Uani 1 1 d . . . . .
H12A H 0.3429 0.5249 0.3277 0.068 Uiso 1 1 calc R U . . .
H12B H 0.2303 0.5210 0.2976 0.068 Uiso 1 1 calc R U . . .
C26 C 0.40705(17) 0.3448(2) 0.94106(14) 0.0625(6) Uani 1 1 d . . . . .
H26 H 0.4290 0.2667 0.9353 0.075 Uiso 1 1 calc R U . . .
C6 C 0.53817(16) 0.2423(2) 0.53029(15) 0.0631(6) Uani 1 1 d . . . . .
H6 H 0.5468 0.3133 0.5013 0.076 Uiso 1 1 calc R U . . .
C21 C 0.18121(18) 0.3253(2) 0.75135(15) 0.0636(6) Uani 1 1 d . . . . .
H21 H 0.2075 0.2883 0.8006 0.076 Uiso 1 1 calc R U . . .
C18 C 0.10334(17) 0.4367(2) 0.60251(15) 0.0650(6) Uani 1 1 d . . . . .
H18 H 0.0773 0.4734 0.5530 0.078 Uiso 1 1 calc R U . . .
C2 C 0.43655(18) 0.1136(2) 0.60682(15) 0.0654(6) Uani 1 1 d . . . . .
H2 H 0.3763 0.0974 0.6286 0.079 Uiso 1 1 calc R U . . .
C24 C 0.35468(18) 0.5289(2) 0.87993(16) 0.0685(7) Uani 1 1 d . . . . .
H24 H 0.3407 0.5771 0.8327 0.082 Uiso 1 1 calc R U . . .
C27 C 0.39515(19) 0.3897(3) 1.02027(15) 0.0739(7) Uani 1 1 d . . . . .
H27 H 0.4089 0.3418 1.0677 0.089 Uiso 1 1 calc R U . . .
C23 C 0.40446(18) 0.3639(3) 0.78379(14) 0.0689(7) Uani 1 1 d . . . . .
H23A H 0.4728 0.3779 0.7728 0.083 Uiso 1 1 calc R U . . .
H23B H 0.3942 0.2783 0.7847 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3232(2) 0.3249(2) 0.24427(14) 0.0736(7) Uani 1 1 d . . . . .
H10A H 0.3309 0.2399 0.2397 0.110 Uiso 1 1 calc R U . . .
H10B H 0.3858 0.3631 0.2392 0.110 Uiso 1 1 calc R U . . .
H10C H 0.2765 0.3525 0.1999 0.110 Uiso 1 1 calc R U . . .
C20 C 0.0824(2) 0.3162(2) 0.72509(18) 0.0762(8) Uani 1 1 d . . . . .
H20 H 0.0412 0.2718 0.7573 0.091 Uiso 1 1 calc R U . . .
C4 C 0.60231(19) 0.0588(2) 0.58730(18) 0.0742(7) Uani 1 1 d . . . . .
H4 H 0.6543 0.0050 0.5955 0.089 Uiso 1 1 calc R U . . .
C29 C 0.3429(2) 0.5732(3) 0.95979(18) 0.0785(7) Uani 1 1 d . . . . .
H29 H 0.3209 0.6510 0.9662 0.094 Uiso 1 1 calc R U . . .
C28 C 0.36366(18) 0.5029(3) 1.02986(16) 0.0749(7) Uani 1 1 d . . . . .
H28 H 0.3561 0.5331 1.0837 0.090 Uiso 1 1 calc R U . . .
C19 C 0.04320(18) 0.3712(3) 0.65233(19) 0.0788(8) Uani 1 1 d . . . . .
H19 H -0.0240 0.3645 0.6365 0.095 Uiso 1 1 calc R U . . .
C11 C 0.18443(18) 0.2993(3) 0.33676(17) 0.0766(7) Uani 1 1 d . . . . .
H11A H 0.1629 0.3141 0.3922 0.115 Uiso 1 1 calc R U . . .
H11B H 0.1884 0.2147 0.3276 0.115 Uiso 1 1 calc R U . . .
H11C H 0.1381 0.3338 0.2948 0.115 Uiso 1 1 calc R U . . .
C5 C 0.61430(18) 0.1617(2) 0.54279(18) 0.0741(7) Uani 1 1 d . . . . .
H5 H 0.6745 0.1773 0.5207 0.089 Uiso 1 1 calc R U . . .
C3 C 0.5146(2) 0.0350(2) 0.61956(18) 0.0769(7) Uani 1 1 d . . . . .
H3 H 0.5071 -0.0346 0.6504 0.092 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C7 1.360(2) . ?
O4 C1 1.395(2) . ?
O1 C15 1.421(3) . ?
O1 H1 0.8200 . ?
O3 C13 1.230(2) . ?
O2 C16 1.217(3) . ?
N1 C16 1.352(3) . ?
N1 C22 1.413(3) . ?
N1 C23 1.444(3) . ?
C7 C14 1.342(3) . ?
C7 C8 1.487(3) . ?
C14 C13 1.457(3) . ?
C14 C15 1.521(3) . ?
C13 C12 1.497(3) . ?
C17 C18 1.374(3) . ?
C17 C22 1.382(3) . ?
C17 C15 1.505(3) . ?
C15 C16 1.548(3) . ?
C22 C21 1.372(3) . ?
C1 C2 1.369(3) . ?
C1 C6 1.370(3) . ?
C9 C12 1.524(3) . ?
C9 C10 1.524(3) . ?
C9 C11 1.524(3) . ?
C9 C8 1.532(3) . ?
C25 C24 1.370(3) . ?
C25 C26 1.379(3) . ?
C25 C23 1.510(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C26 C27 1.372(3) . ?
C26 H26 0.9300 . ?
C6 C5 1.375(3) . ?
C6 H6 0.9300 . ?
C21 C20 1.377(4) . ?
C21 H21 0.9300 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C24 C29 1.379(4) . ?
C24 H24 0.9300 . ?
C27 C28 1.351(4) . ?
C27 H27 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C20 C19 1.376(4) . ?
C20 H20 0.9300 . ?
C4 C3 1.358(4) . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C29 C28 1.371(4) . ?
C29 H29 0.9300 . ?
C28 H28 0.9300 . ?
C19 H19 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5 0.9300 . ?
C3 H3 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 O4 C1 122.99(15) . . ?
C15 O1 H1 109.5 . . ?
C16 N1 C22 111.04(17) . . ?
C16 N1 C23 124.45(19) . . ?
C22 N1 C23 124.17(19) . . ?
C14 C7 O4 115.33(17) . . ?
C14 C7 C8 125.41(18) . . ?
O4 C7 C8 119.03(17) . . ?
C7 C14 C13 118.05(18) . . ?
C7 C14 C15 121.78(17) . . ?
C13 C14 C15 119.84(17) . . ?
O3 C13 C14 121.75(19) . . ?
O3 C13 C12 120.37(18) . . ?
C14 C13 C12 117.88(18) . . ?
C18 C17 C22 119.5(2) . . ?
C18 C17 C15 131.2(2) . . ?
C22 C17 C15 109.30(17) . . ?
O1 C15 C17 113.02(17) . . ?
O1 C15 C14 111.79(16) . . ?
C17 C15 C14 113.20(17) . . ?
O1 C15 C16 104.16(17) . . ?
C17 C15 C16 101.50(16) . . ?
C14 C15 C16 112.39(16) . . ?
C21 C22 C17 122.7(2) . . ?
C21 C22 N1 127.7(2) . . ?
C17 C22 N1 109.66(17) . . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 O4 115.83(19) . . ?
C6 C1 O4 122.48(19) . . ?
C12 C9 C10 109.41(19) . . ?
C12 C9 C11 110.25(19) . . ?
C10 C9 C11 109.61(19) . . ?
C12 C9 C8 107.26(17) . . ?
C10 C9 C8 109.06(18) . . ?
C11 C9 C8 111.20(19) . . ?
O2 C16 N1 125.8(2) . . ?
O2 C16 C15 125.7(2) . . ?
N1 C16 C15 108.46(18) . . ?
C24 C25 C26 118.5(2) . . ?
C24 C25 C23 121.9(2) . . ?
C26 C25 C23 119.5(2) . . ?
C7 C8 C9 113.18(17) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C13 C12 C9 113.46(17) . . ?
C13 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C22 C21 C20 117.1(2) . . ?
C22 C21 H21 121.5 . . ?
C20 C21 H21 121.5 . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C25 C24 C29 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C29 C24 H24 119.8 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
N1 C23 C25 113.90(19) . . ?
N1 C23 H23A 108.8 . . ?
C25 C23 H23A 108.8 . . ?
N1 C23 H23B 108.8 . . ?
C25 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19 C20 C21 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C28 C29 C24 120.3(3) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
C27 C28 C29 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.044

