# 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 2020

####################################################################### 
# 
# 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_T_a
_database_code_depnum_ccdc_archive 'CCDC 1951758'
loop_
_audit_author_name
_audit_author_address
'Anoop  Kumar Panday'
;Deptartment  of Chemistry, Indian Institute of Technology Patna
India
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2020-02-24 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         'C21 H19 N3 O5'
_chemical_formula_sum            'C21 H19 N3 O5'
_chemical_formula_weight         393.39

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2908(7)
_cell_length_b                   11.5745(10)
_cell_length_c                   11.6052(11)
_cell_angle_alpha                64.421(2)
_cell_angle_beta                 78.679(3)
_cell_angle_gamma                78.392(2)
_cell_volume                     976.39(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8006
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      24.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   0.6982
_exptl_transmission_factor_max   0.7451
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20708
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.901
_diffrn_reflns_theta_max         24.683
_diffrn_reflns_theta_full        24.683
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3320
_reflns_number_gt                2262
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0491P)²+0.3011P] 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         3320
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2292(3) 0.8381(2) 0.5216(2) 0.0578(6) Uani 1 1 d . . . . .
H1 H 0.1721 0.8246 0.4680 0.069 Uiso 1 1 calc R U . . .
C2 C 0.1420(3) 0.8731(3) 0.6179(3) 0.0729(8) Uani 1 1 d . . . . .
H2 H 0.0267 0.8819 0.6300 0.087 Uiso 1 1 calc R U . . .
C3 C 0.2250(4) 0.8949(2) 0.6959(2) 0.0698(8) Uani 1 1 d . . . . .
H3 H 0.1658 0.9211 0.7593 0.084 Uiso 1 1 calc R U . . .
C4 C 0.3952(4) 0.8785(2) 0.6811(2) 0.0624(7) Uani 1 1 d . . . . .
H4 H 0.4508 0.8918 0.7357 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4849(3) 0.8420(2) 0.5851(2) 0.0510(6) Uani 1 1 d . . . . .
H5 H 0.6003 0.8306 0.5754 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4011(3) 0.82281(18) 0.50345(19) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.4878(3) 0.79055(18) 0.39453(19) 0.0415(5) Uani 1 1 d . . . . .
C8 C 0.6716(2) 0.73793(18) 0.38984(18) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.7325 0.8067 0.3797 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8302(3) 0.6216(2) 0.5739(2) 0.0450(5) Uani 1 1 d . . . . .
C10 C 0.8510(2) 0.5021(2) 0.69415(19) 0.0433(5) Uani 1 1 d . . . . .
C11 C 0.9042(3) 0.5098(3) 0.7962(2) 0.0605(7) Uani 1 1 d . . . . .
H8 H 0.9325 0.5873 0.7871 0.073 Uiso 1 1 calc R U . . .
C12 C 0.9153(3) 0.4025(4) 0.9113(2) 0.0781(9) Uani 1 1 d . . . . .
H9 H 0.9513 0.4080 0.9796 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8737(3) 0.2886(3) 0.9254(3) 0.0836(9) Uani 1 1 d . . . . .
H10 H 0.8780 0.2175 1.0041 0.100 Uiso 1 1 calc R U . . .
C14 C 0.8255(3) 0.2785(3) 0.8237(3) 0.0769(8) Uani 1 1 d . . . . .
H11 H 0.8011 0.1999 0.8326 0.092 Uiso 1 1 calc R U . . .
C15 C 0.8134(3) 0.3853(2) 0.7082(2) 0.0561(6) Uani 1 1 d . . . . .
H12 H 0.7799 0.3786 0.6397 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7292(3) 0.70651(18) 0.27134(18) 0.0404(5) Uani 1 1 d . . . . .
H13 H 0.8463 0.6701 0.2768 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6439(3) 0.60244(19) 0.2738(2) 0.0409(5) Uani 1 1 d . . . . .
C18 C 0.5855(3) 0.4877(2) 0.1550(2) 0.0651(7) Uani 1 1 d . . . . .
H15 H 0.4687 0.5029 0.1486 0.098 Uiso 1 1 calc R U . . .
H14 H 0.6085 0.4136 0.2329 0.098 Uiso 1 1 calc R U . . .
H16 H 0.6459 0.4722 0.0824 0.098 Uiso 1 1 calc R U . . .
C19 C 0.6652(3) 0.7042(2) 0.0394(2) 0.0551(6) Uani 1 1 d . . . . .
C20 C 0.7200(5) 0.9272(3) -0.0848(2) 0.0943(10) Uani 1 1 d . . . . .
H18 H 0.6153 0.9814 -0.0979 0.141 Uiso 1 1 calc R U . . .
H17 H 0.7536 0.8975 -0.1525 0.141 Uiso 1 1 calc R U . . .
H19 H 0.8019 0.9755 -0.0853 0.141 Uiso 1 1 calc R U . . .
C21 C 0.7273(3) 0.8270(2) 0.1481(2) 0.0494(6) Uani 1 1 d . . . . .
N1 N 0.7096(2) 0.62873(15) 0.50790(15) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.6524 0.5654 0.5373 0.051 Uiso 1 1 calc R U . . .
N2 N 0.6366(2) 0.60152(16) 0.15661(16) 0.0457(5) Uani 1 1 d . . . . .
N3 N 0.7035(2) 0.81524(17) 0.04023(16) 0.0555(5) Uani 1 1 d . . . . .
O1 O 0.41540(18) 0.80668(15) 0.30576(14) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.9131(2) 0.70948(16) 0.53995(17) 0.0751(5) Uani 1 1 d . . . . .
O3 O 0.5937(2) 0.51770(14) 0.37322(14) 0.0558(4) Uani 1 1 d . . . . .
O4 O 0.6539(3) 0.69872(18) -0.06036(16) 0.0878(6) Uani 1 1 d . . . . .
O5 O 0.7537(2) 0.92850(15) 0.14273(15) 0.0736(5) 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 1.375(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.482(3) . ?
C7 O1 1.220(2) . ?
C7 C8 1.523(3) . ?
C8 N1 1.445(2) . ?
C8 C16 1.535(3) . ?
C8 H6 0.9800 . ?
C9 O2 1.221(2) . ?
C9 N1 1.344(2) . ?
C9 C10 1.491(3) . ?
C10 C15 1.382(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.380(4) . ?
C11 H8 0.9300 . ?
C12 C13 1.363(4) . ?
C12 H9 0.9300 . ?
C13 C14 1.375(4) . ?
C13 H10 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H11 0.9300 . ?
C15 H12 0.9300 . ?
C16 C17 1.502(3) . ?
C16 C21 1.506(3) . ?
C16 H13 0.9800 . ?
C17 O3 1.210(2) . ?
C17 N2 1.378(3) . ?
C18 N2 1.472(3) . ?
C18 H15 0.9600 . ?
C18 H14 0.9600 . ?
C18 H16 0.9600 . ?
C19 O4 1.209(3) . ?
C19 N2 1.382(3) . ?
C19 N3 1.389(3) . ?
C20 N3 1.474(3) . ?
C20 H18 0.9600 . ?
C20 H17 0.9600 . ?
C20 H19 0.9600 . ?
C21 O5 1.211(2) . ?
C21 N3 1.371(3) . ?
N1 H7 0.8600 . ?

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 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 118.25(18) . . ?
C5 C6 C7 122.7(2) . . ?
O1 C7 C6 121.34(19) . . ?
O1 C7 C8 118.17(18) . . ?
C6 C7 C8 120.48(17) . . ?
N1 C8 C7 112.03(16) . . ?
N1 C8 C16 112.25(16) . . ?
C7 C8 C16 110.23(16) . . ?
N1 C8 H6 107.3 . . ?
C7 C8 H6 107.3 . . ?
C16 C8 H6 107.3 . . ?
O2 C9 N1 122.05(19) . . ?
O2 C9 C10 122.29(19) . . ?
N1 C9 C10 115.62(18) . . ?
C15 C10 C11 119.2(2) . . ?
C15 C10 C9 122.06(19) . . ?
C11 C10 C9 118.7(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H8 120.0 . . ?
C10 C11 H8 120.0 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H9 119.8 . . ?
C11 C12 H9 119.8 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H10 119.9 . . ?
C14 C13 H10 119.9 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H11 120.0 . . ?
C15 C14 H11 120.0 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H12 119.9 . . ?
C10 C15 H12 119.9 . . ?
C17 C16 C21 114.70(17) . . ?
C17 C16 C8 112.99(16) . . ?
C21 C16 C8 111.67(16) . . ?
C17 C16 H13 105.5 . . ?
C21 C16 H13 105.5 . . ?
C8 C16 H13 105.5 . . ?
O3 C17 N2 120.71(18) . . ?
O3 C17 C16 122.45(18) . . ?
N2 C17 C16 116.66(17) . . ?
N2 C18 H15 109.5 . . ?
N2 C18 H14 109.5 . . ?
H15 C18 H14 109.5 . . ?
N2 C18 H16 109.5 . . ?
H15 C18 H16 109.5 . . ?
H14 C18 H16 109.5 . . ?
O4 C19 N2 121.2(2) . . ?
O4 C19 N3 121.0(2) . . ?
N2 C19 N3 117.7(2) . . ?
N3 C20 H18 109.5 . . ?
N3 C20 H17 109.5 . . ?
H18 C20 H17 109.5 . . ?
N3 C20 H19 109.5 . . ?
H18 C20 H19 109.5 . . ?
H17 C20 H19 109.5 . . ?
O5 C21 N3 121.2(2) . . ?
O5 C21 C16 121.7(2) . . ?
N3 C21 C16 117.00(19) . . ?
C9 N1 C8 123.04(16) . . ?
C9 N1 H7 118.5 . . ?
C8 N1 H7 118.5 . . ?
C17 N2 C19 124.16(18) . . ?
C17 N2 C18 118.57(18) . . ?
C19 N2 C18 117.17(18) . . ?
C21 N3 C19 124.68(18) . . ?
C21 N3 C20 118.51(19) . . ?
C19 N3 C20 116.80(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -177.4(2) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 176.72(19) . . . . ?
C1 C6 C7 O1 17.2(3) . . . . ?
C5 C6 C7 O1 -160.7(2) . . . . ?
C1 C6 C7 C8 -163.67(18) . . . . ?
C5 C6 C7 C8 18.4(3) . . . . ?
O1 C7 C8 N1 -129.31(19) . . . . ?
C6 C7 C8 N1 51.6(2) . . . . ?
O1 C7 C8 C16 -3.5(2) . . . . ?
C6 C7 C8 C16 177.34(16) . . . . ?
O2 C9 C10 C15 -153.0(2) . . . . ?
N1 C9 C10 C15 29.5(3) . . . . ?
O2 C9 C10 C11 29.2(3) . . . . ?
N1 C9 C10 C11 -148.2(2) . . . . ?
C15 C10 C11 C12 -1.6(3) . . . . ?
C9 C10 C11 C12 176.2(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C12 C13 C14 C15 -2.3(4) . . . . ?
C13 C14 C15 C10 0.5(4) . . . . ?
C11 C10 C15 C14 1.4(3) . . . . ?
C9 C10 C15 C14 -176.3(2) . . . . ?
N1 C8 C16 C17 62.7(2) . . . . ?
C7 C8 C16 C17 -62.9(2) . . . . ?
N1 C8 C16 C21 -166.18(16) . . . . ?
C7 C8 C16 C21 68.2(2) . . . . ?
C21 C16 C17 O3 -158.7(2) . . . . ?
C8 C16 C17 O3 -29.2(3) . . . . ?
C21 C16 C17 N2 26.2(3) . . . . ?
C8 C16 C17 N2 155.75(17) . . . . ?
C17 C16 C21 O5 161.7(2) . . . . ?
C8 C16 C21 O5 31.5(3) . . . . ?
C17 C16 C21 N3 -21.8(3) . . . . ?
C8 C16 C21 N3 -152.01(19) . . . . ?
O2 C9 N1 C8 2.1(3) . . . . ?
C10 C9 N1 C8 179.59(18) . . . . ?
C7 C8 N1 C9 -128.2(2) . . . . ?
C16 C8 N1 C9 107.1(2) . . . . ?
O3 C17 N2 C19 168.8(2) . . . . ?
C16 C17 N2 C19 -16.0(3) . . . . ?
O3 C17 N2 C18 -7.4(3) . . . . ?
C16 C17 N2 C18 167.78(18) . . . . ?
O4 C19 N2 C17 -178.6(2) . . . . ?
N3 C19 N2 C17 -0.2(3) . . . . ?
O4 C19 N2 C18 -2.3(3) . . . . ?
N3 C19 N2 C18 176.1(2) . . . . ?
O5 C21 N3 C19 -176.9(2) . . . . ?
C16 C21 N3 C19 6.6(3) . . . . ?
O5 C21 N3 C20 3.4(4) . . . . ?
C16 C21 N3 C20 -173.1(2) . . . . ?
O4 C19 N3 C21 -176.4(2) . . . . ?
N2 C19 N3 C21 5.2(3) . . . . ?
O4 C19 N3 C20 3.3(4) . . . . ?
N2 C19 N3 C20 -175.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H7 O3 0.86 2.29 3.071(2) 150.4 2_666
N1 H7 O3 0.86 2.36 2.800(2) 112.6 .
C20 H18 O1 0.96 2.60 3.200(3) 120.6 2_675

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_MM_a
_database_code_depnum_ccdc_archive 'CCDC 1979332'
loop_
_audit_author_name
_audit_author_address
'Dr.Md.Lokman H.Choudhury'
;Indian Institute of Technology Patna
India
;
_audit_update_record             
;
2020-01-22 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'5-(2-(4-chlorophenyl)-4-phenylthiazol-5-yl)-6-hydroxy-1,3-dimethylpyrimidine-2,4 (1H, 3H)-dione'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 Cl N3 O3 S'
_chemical_formula_sum            'C21 H16 Cl N3 O3 S'
_chemical_formula_weight         425.88

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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                   10.5250(10)
_cell_length_b                   8.9515(10)
_cell_length_c                   20.771(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.225(3)
_cell_angle_gamma                90
_cell_volume                     1919.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5725
_cell_measurement_theta_min      2.485
_cell_measurement_theta_max      26.459

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            21336
_diffrn_reflns_av_unetI/netI     0.1310
_diffrn_reflns_av_R_equivalents  0.1310
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             21336
_reflns_number_gt                11977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+2.6509P] 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       0.0043(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         21336
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8288(5) 0.3504(6) 0.3397(3) 0.0311(14) Uani 1 1 d . . . . .
C2 C 0.9139(6) 0.2589(6) 0.4522(3) 0.0511(18) Uani 1 1 d . . . . .
H2 H 0.8509 0.3014 0.4747 0.077 Uiso 1 1 calc R U . . .
H4 H 0.9966 0.2553 0.4815 0.077 Uiso 1 1 calc R U . . .
H3 H 0.8878 0.1595 0.4380 0.077 Uiso 1 1 calc R U . . .
C3 C 1.0306(6) 0.4438(6) 0.4008(3) 0.0390(16) Uani 1 1 d . . . . .
C4 C 1.1473(5) 0.6327(7) 0.3525(3) 0.0574(19) Uani 1 1 d . . . . .
H6 H 1.2241 0.5739 0.3661 0.086 Uiso 1 1 calc R U . . .
H5 H 1.1444 0.7105 0.3840 0.086 Uiso 1 1 calc R U . . .
H7 H 1.1484 0.6763 0.3104 0.086 Uiso 1 1 calc R U . . .
C5 C 0.9331(5) 0.5519(6) 0.2937(3) 0.0304(14) Uani 1 1 d . . . . .
C6 C 0.8306(5) 0.4456(6) 0.2884(2) 0.0267(13) Uani 1 1 d . . . . .
C7 C 0.7189(5) 0.4550(6) 0.2336(3) 0.0287(13) Uani 1 1 d . . . . .
C8 C 0.7001(5) 0.4047(5) 0.1704(3) 0.0267(13) Uani 1 1 d . . . . .
C9 C 0.7953(5) 0.3234(6) 0.1397(2) 0.0263(13) Uani 1 1 d . . . . .
C10 C 0.9259(5) 0.3597(6) 0.1532(2) 0.0336(14) Uani 1 1 d . . . . .
H8 H 0.9541 0.4415 0.1798 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0142(5) 0.2760(7) 0.1278(3) 0.0398(16) Uani 1 1 d . . . . .
H9 H 1.1013 0.3022 0.1369 0.048 Uiso 1 1 calc R U . . .
C12 C 0.9743(6) 0.1545(7) 0.0892(3) 0.0450(16) Uani 1 1 d . . . . .
H10 H 1.0349 0.0960 0.0737 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8446(6) 0.1184(6) 0.0734(3) 0.0406(16) Uani 1 1 d . . . . .
H11 H 0.8172 0.0373 0.0462 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7554(5) 0.2037(6) 0.0981(3) 0.0349(15) Uani 1 1 d . . . . .
H12 H 0.6678 0.1805 0.0869 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5054(5) 0.5049(6) 0.1669(2) 0.0315(14) Uani 1 1 d . . . . .
C16 C 0.3730(5) 0.5568(6) 0.1411(3) 0.0322(14) Uani 1 1 d . . . . .
C17 C 0.3170(5) 0.5349(6) 0.0761(3) 0.0409(15) Uani 1 1 d . . . . .
H13 H 0.3630 0.4854 0.0486 0.049 Uiso 1 1 calc R U . . .
C18 C 0.1928(5) 0.5858(6) 0.0512(3) 0.0426(16) Uani 1 1 d . . . . .
H14 H 0.1553 0.5700 0.0074 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1262(5) 0.6591(6) 0.0914(3) 0.0422(16) Uani 1 1 d . . . . .
C20 C 0.1788(6) 0.6832(7) 0.1558(3) 0.059(2) Uani 1 1 d . . . . .
H15 H 0.1321 0.7331 0.1828 0.070 Uiso 1 1 calc R U . . .
C21 C 0.3025(6) 0.6323(7) 0.1802(3) 0.0559(18) Uani 1 1 d . . . . .
H16 H 0.3392 0.6492 0.2241 0.067 Uiso 1 1 calc R U . . .
Cl1 Cl -0.03021(15) 0.7213(2) 0.06144(8) 0.0677(6) Uani 1 1 d . . . . .
N1 N 0.9237(4) 0.3515(5) 0.3949(2) 0.0334(11) Uani 1 1 d . . . . .
N2 N 1.0334(4) 0.5375(5) 0.3479(2) 0.0362(12) Uani 1 1 d . . . . .
N3 N 0.5787(4) 0.4329(5) 0.1328(2) 0.0303(11) Uani 1 1 d . . . . .
O1 O 0.7376(4) 0.2515(4) 0.34342(16) 0.0396(10) Uani 1 1 d . . . . .
H1 H 0.6886 0.2447 0.3077 0.059 Uiso 1 1 calc R U . . .
O2 O 1.1166(4) 0.4438(4) 0.4488(2) 0.0595(13) Uani 1 1 d . . . . .
O3 O 0.9392(3) 0.6535(4) 0.25342(17) 0.0374(10) Uani 1 1 d . . . . .
S1 S 0.57989(13) 0.54121(16) 0.24706(7) 0.0353(4) 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 O1 1.319(6) . ?
C1 N1 1.365(6) . ?
C1 C6 1.367(7) . ?
C2 N1 1.472(6) . ?
C2 H2 0.9600 . ?
C2 H4 0.9600 . ?
C2 H3 0.9600 . ?
C3 O2 1.210(6) . ?
C3 N1 1.382(6) . ?
C3 N2 1.386(7) . ?
C4 N2 1.459(6) . ?
C4 H6 0.9600 . ?
C4 H5 0.9600 . ?
C4 H7 0.9600 . ?
C5 O3 1.246(6) . ?
C5 N2 1.392(6) . ?
C5 C6 1.426(7) . ?
C6 C7 1.471(6) . ?
C7 C8 1.365(6) . ?
C7 S1 1.725(5) . ?
C8 N3 1.385(6) . ?
C8 C9 1.480(7) . ?
C9 C10 1.387(6) . ?
C9 C14 1.388(6) . ?
C10 C11 1.377(7) . ?
C10 H8 0.9300 . ?
C11 C12 1.367(7) . ?
C11 H9 0.9300 . ?
C12 C13 1.379(7) . ?
C12 H10 0.9300 . ?
C13 C14 1.385(7) . ?
C13 H11 0.9300 . ?
C14 H12 0.9300 . ?
C15 N3 1.313(6) . ?
C15 C16 1.468(7) . ?
C15 S1 1.728(5) . ?
C16 C17 1.378(7) . ?
C16 C21 1.379(7) . ?
C17 C18 1.386(7) . ?
C17 H13 0.9300 . ?
C18 C19 1.359(7) . ?
C18 H14 0.9300 . ?
C19 C20 1.361(7) . ?
C19 Cl1 1.734(5) . ?
C20 C21 1.380(7) . ?
C20 H15 0.9300 . ?
C21 H16 0.9300 . ?
O1 H1 0.8200 . ?

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
O1 C1 N1 112.2(5) . . ?
O1 C1 C6 125.8(5) . . ?
N1 C1 C6 122.0(5) . . ?
N1 C2 H2 109.5 . . ?
N1 C2 H4 109.5 . . ?
H2 C2 H4 109.5 . . ?
N1 C2 H3 109.5 . . ?
H2 C2 H3 109.5 . . ?
H4 C2 H3 109.5 . . ?
O2 C3 N1 122.6(6) . . ?
O2 C3 N2 121.7(6) . . ?
N1 C3 N2 115.7(5) . . ?
N2 C4 H6 109.5 . . ?
N2 C4 H5 109.5 . . ?
H6 C4 H5 109.5 . . ?
N2 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
O3 C5 N2 118.7(5) . . ?
O3 C5 C6 125.0(5) . . ?
N2 C5 C6 116.3(5) . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 C7 120.6(5) . . ?
C5 C6 C7 120.0(5) . . ?
C8 C7 C6 132.1(5) . . ?
C8 C7 S1 109.6(4) . . ?
C6 C7 S1 118.4(4) . . ?
C7 C8 N3 115.3(5) . . ?
C7 C8 C9 126.4(5) . . ?
N3 C8 C9 118.3(5) . . ?
C10 C9 C14 118.4(5) . . ?
C10 C9 C8 121.6(5) . . ?
C14 C9 C8 120.0(5) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H8 119.6 . . ?
C9 C10 H8 119.6 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H9 119.8 . . ?
C10 C11 H9 119.8 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H10 119.9 . . ?
C13 C12 H10 119.9 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H11 120.2 . . ?
C14 C13 H11 120.2 . . ?
C13 C14 C9 120.8(5) . . ?
C13 C14 H12 119.6 . . ?
C9 C14 H12 119.6 . . ?
N3 C15 C16 125.1(5) . . ?
N3 C15 S1 114.1(4) . . ?
C16 C15 S1 120.8(4) . . ?
C17 C16 C21 118.1(5) . . ?
C17 C16 C15 120.5(5) . . ?
C21 C16 C15 121.4(5) . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H13 119.6 . . ?
C18 C17 H13 119.6 . . ?
C19 C18 C17 119.4(5) . . ?
C19 C18 H14 120.3 . . ?
C17 C18 H14 120.3 . . ?
C18 C19 C20 121.3(5) . . ?
C18 C19 Cl1 120.1(5) . . ?
C20 C19 Cl1 118.6(5) . . ?
C19 C20 C21 118.9(6) . . ?
C19 C20 H15 120.5 . . ?
C21 C20 H15 120.5 . . ?
C16 C21 C20 121.5(6) . . ?
C16 C21 H16 119.3 . . ?
C20 C21 H16 119.3 . . ?
C1 N1 C3 121.9(5) . . ?
C1 N1 C2 121.4(5) . . ?
C3 N1 C2 116.7(5) . . ?
C3 N2 C5 124.6(5) . . ?
C3 N2 C4 116.5(5) . . ?
C5 N2 C4 118.9(5) . . ?
C15 N3 C8 111.1(4) . . ?
C1 O1 H1 109.5 . . ?
C7 S1 C15 90.0(3) . . ?

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 C1 C6 C5 176.5(5) . . . . ?
N1 C1 C6 C5 -1.7(7) . . . . ?
O1 C1 C6 C7 6.1(8) . . . . ?
N1 C1 C6 C7 -172.0(4) . . . . ?
O3 C5 C6 C1 -172.9(5) . . . . ?
N2 C5 C6 C1 7.9(7) . . . . ?
O3 C5 C6 C7 -2.4(8) . . . . ?
N2 C5 C6 C7 178.4(4) . . . . ?
C1 C6 C7 C8 -106.4(7) . . . . ?
C5 C6 C7 C8 83.3(7) . . . . ?
C1 C6 C7 S1 72.3(6) . . . . ?
C5 C6 C7 S1 -97.9(5) . . . . ?
C6 C7 C8 N3 178.8(5) . . . . ?
S1 C7 C8 N3 0.0(6) . . . . ?
C6 C7 C8 C9 -0.4(9) . . . . ?
S1 C7 C8 C9 -179.3(4) . . . . ?
C7 C8 C9 C10 -38.5(8) . . . . ?
N3 C8 C9 C10 142.2(5) . . . . ?
C7 C8 C9 C14 138.9(5) . . . . ?
N3 C8 C9 C14 -40.4(7) . . . . ?
C14 C9 C10 C11 -2.1(8) . . . . ?
C8 C9 C10 C11 175.4(5) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C13 2.6(9) . . . . ?
C11 C12 C13 C14 -1.7(9) . . . . ?
C12 C13 C14 C9 -1.1(8) . . . . ?
C10 C9 C14 C13 3.0(8) . . . . ?
C8 C9 C14 C13 -174.5(5) . . . . ?
N3 C15 C16 C17 -1.7(8) . . . . ?
S1 C15 C16 C17 176.3(4) . . . . ?
N3 C15 C16 C21 -179.8(5) . . . . ?
S1 C15 C16 C21 -1.9(7) . . . . ?
C21 C16 C17 C18 -0.8(8) . . . . ?
C15 C16 C17 C18 -179.0(5) . . . . ?
C16 C17 C18 C19 0.5(9) . . . . ?
C17 C18 C19 C20 -0.2(9) . . . . ?
C17 C18 C19 Cl1 -179.1(4) . . . . ?
C18 C19 C20 C21 0.3(10) . . . . ?
Cl1 C19 C20 C21 179.1(5) . . . . ?
C17 C16 C21 C20 0.8(9) . . . . ?
C15 C16 C21 C20 179.0(5) . . . . ?
C19 C20 C21 C16 -0.6(10) . . . . ?
O1 C1 N1 C3 178.2(4) . . . . ?
C6 C1 N1 C3 -3.4(8) . . . . ?
O1 C1 N1 C2 -4.5(7) . . . . ?
C6 C1 N1 C2 173.9(5) . . . . ?
O2 C3 N1 C1 -178.5(5) . . . . ?
N2 C3 N1 C1 1.7(7) . . . . ?
O2 C3 N1 C2 4.1(8) . . . . ?
N2 C3 N1 C2 -175.7(4) . . . . ?
O2 C3 N2 C5 -174.5(5) . . . . ?
N1 C3 N2 C5 5.4(8) . . . . ?
O2 C3 N2 C4 1.8(8) . . . . ?
N1 C3 N2 C4 -178.4(4) . . . . ?
O3 C5 N2 C3 170.6(5) . . . . ?
C6 C5 N2 C3 -10.1(7) . . . . ?
O3 C5 N2 C4 -5.6(7) . . . . ?
C6 C5 N2 C4 173.7(4) . . . . ?
C16 C15 N3 C8 177.6(5) . . . . ?
S1 C15 N3 C8 -0.5(5) . . . . ?
C7 C8 N3 C15 0.3(6) . . . . ?
C9 C8 N3 C15 179.7(4) . . . . ?
C8 C7 S1 C15 -0.2(4) . . . . ?
C6 C7 S1 C15 -179.2(4) . . . . ?
N3 C15 S1 C7 0.4(4) . . . . ?
C16 C15 S1 C7 -177.7(4) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.075


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
