# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_MAL_TOL_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2110512'
loop_
_audit_author_name
_audit_author_address
'Ranajit Das'
;Shiv Nadar University
India
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N3 O6'
_chemical_formula_sum            'C26 H25 N3 O6'
_chemical_formula_weight         475.49

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   12.6825(3)
_cell_length_b                   14.3250(4)
_cell_length_c                   26.5675(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4826.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4934
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.397

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50005
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4921
_reflns_number_gt                3233
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1491P)²+12.4193P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0034(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4921
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.1071
_refine_ls_wR_factor_ref         0.3348
_refine_ls_wR_factor_gt          0.2880
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O3 O 0.5896(3) 0.4397(3) 0.35048(13) 0.0584(9) Uani 1 1 d . . . . .
O2 O 0.4252(3) 0.3061(3) 0.46704(14) 0.0753(9) Uani 1 1 d . . . . .
O4 O 0.3819(3) 0.5784(3) 0.46763(13) 0.0626(10) Uani 1 1 d . . . . .
O5 O 0.1663(3) 0.5103(3) 0.49075(14) 0.0641(10) Uani 1 1 d . . . . .
N2 N 0.5052(3) 0.5187(2) 0.41335(13) 0.0425(9) Uani 1 1 d . . . . .
N1 N 0.5595(3) 0.2427(3) 0.42114(15) 0.0539(10) Uani 1 1 d . . . . .
O6 O 0.1458(4) 0.6063(3) 0.42490(16) 0.0842(14) Uani 1 1 d . . . . .
N3 N 0.3773(4) 0.5229(3) 0.30193(16) 0.0643(12) Uani 1 1 d . . . . .
C10 C 0.3357(3) 0.4609(3) 0.40620(15) 0.0400(9) Uani 1 1 d . . . . .
C6 C 0.4025(3) 0.4094(3) 0.36673(15) 0.0402(9) Uani 1 1 d . . . . .
C7 C 0.5102(3) 0.4561(3) 0.37397(15) 0.0410(9) Uani 1 1 d . . . . .
C9 C 0.4053(4) 0.5259(4) 0.4338(2) 0.0625(10) Uani 1 1 d . . . . .
C5 C 0.4626(4) 0.2853(3) 0.42701(15) 0.0444(10) Uani 1 1 d . . . . .
C11 C 0.2310(4) 0.4619(3) 0.41160(16) 0.0443(10) Uani 1 1 d . . . . .
C4 C 0.4148(4) 0.3030(3) 0.37563(15) 0.0427(10) Uani 1 1 d . . . . .
H25 H 0.345439 0.273135 0.373765 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1564(3) 0.3999(3) 0.38475(17) 0.0450(10) Uani 1 1 d . . . . .
C26 C 0.3596(4) 0.4342(4) 0.31450(19) 0.0595(10) Uani 1 1 d . . . . .
C21 C 0.1517(4) 0.3053(3) 0.39611(17) 0.0486(11) Uani 1 1 d . . . . .
H13 H 0.194151 0.280845 0.421396 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5945(6) 0.5731(5) 0.4302(3) 0.0890(15) Uani 1 1 d . . . . .
H00A H 0.570059 0.630185 0.445058 0.134 Uiso 1 1 calc R U . . .
H00B H 0.639048 0.587168 0.401939 0.134 Uiso 1 1 calc R U . . .
H00C H 0.633724 0.538070 0.454613 0.134 Uiso 1 1 calc R U . . .
C12 C 0.1785(4) 0.5361(3) 0.4430(2) 0.0546(12) Uani 1 1 d . . . . .
C18 C 0.0178(4) 0.2815(4) 0.33239(18) 0.0526(11) Uani 1 1 d . . . . .
C3 C 0.4914(4) 0.2528(3) 0.33982(17) 0.0521(11) Uani 1 1 d . . . . .
H00D H 0.457738 0.198912 0.324656 0.063 Uiso 1 1 calc R U . . .
H24 H 0.514376 0.294561 0.313253 0.063 Uiso 1 1 calc R U . . .
C22 C 0.3023(4) 0.3745(4) 0.28479(17) 0.0542(12) Uani 1 1 d . . . . .
H23 H 0.292084 0.312736 0.294433 0.065 Uiso 1 1 calc R U . . .
C20 C 0.0839(4) 0.2478(4) 0.36989(18) 0.0534(12) Uani 1 1 d . . . . .
H14 H 0.082461 0.184426 0.377546 0.064 Uiso 1 1 calc R U . . .
C16 C 0.0903(4) 0.4342(4) 0.3473(2) 0.0593(13) Uani 1 1 d . . . . .
H19 H 0.091232 0.497578 0.339788 0.071 Uiso 1 1 calc R U . . .
C17 C 0.0234(4) 0.3759(4) 0.3212(2) 0.0611(13) Uani 1 1 d . . . . .
H18 H -0.018613 0.400185 0.295679 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5822(4) 0.2235(4) 0.3712(2) 0.0620(14) Uani 1 1 d . . . . .
C23 C 0.2601(4) 0.4077(5) 0.24021(19) 0.0675(15) Uani 1 1 d . . . . .
H22 H 0.220614 0.368429 0.219673 0.081 Uiso 1 1 calc R U . . .
C19 C -0.0582(5) 0.2169(4) 0.3061(2) 0.0673(14) Uani 1 1 d . . . . .
H15 H -0.040524 0.153335 0.313843 0.101 Uiso 1 1 calc R U . . .
H17 H -0.053853 0.226421 0.270387 0.101 Uiso 1 1 calc R U . . .
H16 H -0.128708 0.229752 0.317310 0.101 Uiso 1 1 calc R U . . .
C25 C 0.3363(4) 0.5532(4) 0.25813(18) 0.0595(10) Uani 1 1 d . . . . .
H20 H 0.348831 0.614655 0.248546 0.071 Uiso 1 1 calc R U . . .
C24 C 0.2765(5) 0.4973(5) 0.2267(2) 0.0792(18) Uani 1 1 d . . . . .
H21 H 0.248258 0.520930 0.196999 0.095 Uiso 1 1 calc R U . . .
C27 C 0.6271(6) 0.2196(5) 0.4631(2) 0.0844(19) Uani 1 1 d . . . . .
H26 H 0.619866 0.266227 0.488852 0.127 Uiso 1 1 calc R U . . .
H28 H 0.699037 0.217317 0.452000 0.127 Uiso 1 1 calc R U . . .
H27 H 0.607215 0.159812 0.476477 0.127 Uiso 1 1 calc R U . . .
C13 C 0.1169(5) 0.5805(4) 0.52311(19) 0.0625(10) Uani 1 1 d . . . . .
H9 H 0.132606 0.642415 0.510337 0.075 Uiso 1 1 calc R U . . .
H8 H 0.040966 0.572321 0.522684 0.075 Uiso 1 1 calc R U . . .
C14 C 0.1539(6) 0.5724(6) 0.5723(2) 0.0890(15) Uani 1 1 d . . . . .
H12 H 0.147546 0.508783 0.583219 0.134 Uiso 1 1 calc R U . . .
H10 H 0.113013 0.611920 0.594058 0.134 Uiso 1 1 calc R U . . .
H11 H 0.226546 0.591046 0.573618 0.134 Uiso 1 1 calc R U . . .
O1 O 0.6636(3) 0.1867(3) 0.35715(14) 0.0753(9) 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
O3 C7 1.207(5) . ?
O2 C5 1.203(5) . ?
O4 C9 1.208(6) . ?
O5 C12 1.331(6) . ?
O5 C13 1.464(6) . ?
N2 C7 1.380(5) . ?
N2 C9 1.383(6) . ?
N2 C8 1.446(8) . ?
N1 C5 1.380(6) . ?
N1 C2 1.385(7) . ?
N1 C27 1.446(7) . ?
O6 C12 1.189(6) . ?
N3 C26 1.333(7) . ?
N3 C25 1.347(6) . ?
C10 C11 1.335(6) . ?
C10 C9 1.478(7) . ?
C10 C6 1.537(6) . ?
C6 C26 1.532(6) . ?
C6 C7 1.534(6) . ?
C6 C4 1.549(6) . ?
C5 C4 1.515(6) . ?
C11 C15 1.481(6) . ?
C11 C12 1.506(6) . ?
C4 C3 1.538(6) . ?
C15 C21 1.389(6) . ?
C15 C16 1.390(7) . ?
C26 C22 1.372(7) . ?
C21 C20 1.380(7) . ?
C18 C17 1.385(7) . ?
C18 C20 1.389(7) . ?
C18 C19 1.508(7) . ?
C3 C2 1.482(7) . ?
C22 C23 1.384(7) . ?
C16 C17 1.378(7) . ?
C2 O1 1.218(6) . ?
C23 C24 1.349(9) . ?
C25 C24 1.384(8) . ?
C13 C14 1.394(8) . ?

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
C12 O5 C13 114.8(4) . . ?
C7 N2 C9 112.9(4) . . ?
C7 N2 C8 123.2(4) . . ?
C9 N2 C8 123.8(4) . . ?
C5 N1 C2 112.4(4) . . ?
C5 N1 C27 122.8(5) . . ?
C2 N1 C27 124.8(5) . . ?
C26 N3 C25 117.3(5) . . ?
C11 C10 C9 122.2(4) . . ?
C11 C10 C6 128.8(4) . . ?
C9 C10 C6 108.2(4) . . ?
C26 C6 C7 109.2(4) . . ?
C26 C6 C10 108.1(4) . . ?
C7 C6 C10 101.3(3) . . ?
C26 C6 C4 113.7(4) . . ?
C7 C6 C4 108.7(3) . . ?
C10 C6 C4 115.1(3) . . ?
O3 C7 N2 123.9(4) . . ?
O3 C7 C6 126.4(4) . . ?
N2 C7 C6 109.7(3) . . ?
O4 C9 N2 124.3(5) . . ?
O4 C9 C10 127.9(5) . . ?
N2 C9 C10 107.8(4) . . ?
O2 C5 N1 124.2(4) . . ?
O2 C5 C4 126.6(4) . . ?
N1 C5 C4 109.2(4) . . ?
C10 C11 C15 125.2(4) . . ?
C10 C11 C12 120.5(4) . . ?
C15 C11 C12 114.0(4) . . ?
C5 C4 C3 103.0(4) . . ?
C5 C4 C6 110.1(3) . . ?
C3 C4 C6 115.4(4) . . ?
C21 C15 C16 118.3(4) . . ?
C21 C15 C11 120.5(4) . . ?
C16 C15 C11 121.2(4) . . ?
N3 C26 C22 122.6(5) . . ?
N3 C26 C6 112.8(4) . . ?
C22 C26 C6 124.4(5) . . ?
C20 C21 C15 120.0(4) . . ?
O6 C12 O5 125.4(5) . . ?
O6 C12 C11 121.8(5) . . ?
O5 C12 C11 112.5(4) . . ?
C17 C18 C20 117.6(5) . . ?
C17 C18 C19 122.2(5) . . ?
C20 C18 C19 120.3(5) . . ?
C2 C3 C4 106.0(4) . . ?
C26 C22 C23 118.9(5) . . ?
C21 C20 C18 122.0(5) . . ?
C17 C16 C15 121.2(5) . . ?
C16 C17 C18 121.0(5) . . ?
O1 C2 N1 123.8(5) . . ?
O1 C2 C3 127.5(5) . . ?
N1 C2 C3 108.7(4) . . ?
C24 C23 C22 119.7(5) . . ?
N3 C25 C24 123.1(5) . . ?
C23 C24 C25 118.3(5) . . ?
C14 C13 O5 110.5(5) . . ?

_refine_diff_density_max         1.450
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.081

