# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sub-musa-nsa1
_database_code_depnum_ccdc_archive 'CCDC 1901104'
loop_
_audit_author_name
_audit_author_address
'Dr. Md. Musawwer Khan '
;Aligarh Muslim University 
India
;
_audit_update_record             
;
2019-03-05 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-22
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 N4 O3'
_chemical_formula_sum            'C20 H18 N4 O3'
_chemical_compound_source        synthesized
_chemical_formula_weight         362.38
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      293(2)
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7875(3)
_cell_length_b                   20.8262(4)
_cell_length_c                   8.0335(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.106(2)
_cell_angle_gamma                90
_cell_volume                     1782.08(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8450
_cell_measurement_theta_min      3.2240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21157
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.399
_diffrn_reflns_theta_min         3.228
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  54.00   0.50    8.00    --   -9.95   0.00  30.00   94
  2  ω    -58.00 -32.00   0.50    8.00    --   -9.95 125.00  30.00   52
  3  ω    -62.00 -36.00   0.50    8.00    --   -9.95   0.00  30.00   52
  4  ω    -28.00   0.00   0.50    8.00    --   10.22 121.00 -47.63   56
  5  ω      3.00  80.00   0.50    8.00    --   10.22  19.00-120.00  154
  6  ω    -53.00  25.00   0.50    8.00    --   10.22 -57.00 -60.00  156
  7  ω    -19.00  40.00   0.50    8.00    --   10.22 -99.00 150.00  118
  8  ω      3.00  58.00   0.50    8.00    --   10.22-125.00  60.00  110
  9  ω    -38.00 -11.00   0.50    8.00    --   10.22 130.00 143.95   54
 10  ω    -15.00  38.00   0.50    8.00    --   10.22  77.00 -60.00  106
 11  ω    -52.00  13.00   0.50    8.00    --   10.22 -57.00-120.00  130
 12  ω      1.00  72.00   0.50    8.00    --   10.22  38.00 120.00  142
 13  ω     22.00  59.00   0.50    8.00    --   10.22-125.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0573181000
_diffrn_orient_matrix_UB_12      0.0113906000
_diffrn_orient_matrix_UB_13      -0.0460364000
_diffrn_orient_matrix_UB_21      -0.0332933000
_diffrn_orient_matrix_UB_22      -0.0140512000
_diffrn_orient_matrix_UB_23      0.0601842000
_diffrn_orient_matrix_UB_31      0.0063578000
_diffrn_orient_matrix_UB_32      0.0288561000
_diffrn_orient_matrix_UB_33      0.0474666000
_diffrn_oxdiff_ac3_digest_frames 
;
010e50c2c50349d56baf0967d9729056b800025e7e1
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f2a90113f000a8df155f7c38faf6697c116a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2915
_reflns_number_total             3846
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+0.2323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C16(H16), C9(H9), C5(H5), C8(H8), C17(H17), C20(H20), C18(H18),
 C7(H7), C6(H6), C19(H19)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56600(9) 0.65613(5) 0.47983(14) 0.0517(3) Uani 1 1 d . . . . .
O2 O 0.22622(11) 0.52520(5) 0.27087(14) 0.0609(3) Uani 1 1 d . . . . .
O3 O 0.41585(11) 0.49211(5) 0.25414(14) 0.0626(3) Uani 1 1 d . . . . .
N4 N 0.34232(13) 0.53377(6) 0.29992(15) 0.0497(3) Uani 1 1 d . . . . .
N3 N 0.60648(12) 0.56370(6) 0.36919(16) 0.0505(3) Uani 1 1 d . . . . .
H3 H 0.585530 0.528073 0.318285 0.061 Uiso 1 1 calc R . . . .
N1 N 0.51573(11) 0.76252(6) 0.54767(16) 0.0472(3) Uani 1 1 d . . . . .
N2 N 0.41058(11) 0.79876(6) 0.55609(16) 0.0504(3) Uani 1 1 d . . . . .
C13 C 0.51666(14) 0.60074(6) 0.40617(17) 0.0436(3) Uani 1 1 d . . . . .
C15 C 0.23125(13) 0.60383(7) 0.58173(17) 0.0427(3) Uani 1 1 d . . . . .
C2 C 0.35445(13) 0.69588(7) 0.48721(17) 0.0427(3) Uani 1 1 d . . . . .
C1 C 0.48009(13) 0.70156(6) 0.50547(18) 0.0436(3) Uani 1 1 d . . . . .
C11 C 0.29028(13) 0.63308(7) 0.43811(17) 0.0438(3) Uani 1 1 d . . . . .
H11 H 0.223700 0.640623 0.342066 0.053 Uiso 1 1 calc R . . . .
C4 C 0.63641(13) 0.79101(7) 0.55431(18) 0.0438(3) Uani 1 1 d . . . . .
C12 C 0.38728(13) 0.58929(6) 0.38176(16) 0.0427(3) Uani 1 1 d . . . . .
C16 C 0.30587(14) 0.58880(7) 0.73194(18) 0.0485(4) Uani 1 1 d . . . . .
H16 H 0.391458 0.597430 0.745351 0.058 Uiso 1 1 calc R . . . .
C9 C 0.64716(14) 0.85052(7) 0.48100(19) 0.0503(4) Uani 1 1 d . . . . .
H9 H 0.575650 0.872725 0.432640 0.060 Uiso 1 1 calc R . . . .
C3 C 0.31445(13) 0.75834(7) 0.52099(18) 0.0470(3) Uani 1 1 d . . . . .
C5 C 0.74214(14) 0.75874(8) 0.6296(2) 0.0541(4) Uani 1 1 d . . . . .
H5 H 0.734865 0.719375 0.681800 0.065 Uiso 1 1 calc R . . . .
C8 C 0.76448(15) 0.87668(8) 0.4801(2) 0.0583(4) Uani 1 1 d . . . . .
H8 H 0.772044 0.916609 0.430872 0.070 Uiso 1 1 calc R . . . .
C17 C 0.25640(16) 0.56125(8) 0.8628(2) 0.0585(4) Uani 1 1 d . . . . .
H17 H 0.308714 0.550997 0.962678 0.070 Uiso 1 1 calc R . . . .
C20 C 0.10391(14) 0.59127(8) 0.5664(2) 0.0596(4) Uani 1 1 d . . . . .
H20 H 0.051330 0.601440 0.466637 0.071 Uiso 1 1 calc R . . . .
C18 C 0.13030(17) 0.54891(8) 0.8461(2) 0.0619(4) Uani 1 1 d . . . . .
H18 H 0.096666 0.530608 0.934688 0.074 Uiso 1 1 calc R . . . .
C7 C 0.86994(16) 0.84410(8) 0.5514(2) 0.0644(5) Uani 1 1 d . . . . .
H7 H 0.948946 0.861604 0.548979 0.077 Uiso 1 1 calc R . . . .
C14 C 0.73930(14) 0.57895(8) 0.4087(2) 0.0596(4) Uani 1 1 d . . . . .
H14A H 0.755696 0.618285 0.353763 0.089 Uiso 1 1 calc GR . . . .
H14B H 0.787456 0.544874 0.369891 0.089 Uiso 1 1 calc GR . . . .
H14C H 0.762513 0.583756 0.528377 0.089 Uiso 1 1 calc GR . . . .
C6 C 0.85889(15) 0.78540(8) 0.6267(2) 0.0657(5) Uani 1 1 d . . . . .
H6 H 0.930619 0.763570 0.675869 0.079 Uiso 1 1 calc R . . . .
C10 C 0.18299(14) 0.78032(8) 0.5195(2) 0.0631(4) Uani 1 1 d . . . . .
H10A H 0.146220 0.756642 0.601830 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.135142 0.773229 0.409698 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.182808 0.825278 0.545839 0.095 Uiso 1 1 calc GR . . . .
C19 C 0.05409(16) 0.56374(9) 0.6980(2) 0.0691(5) Uani 1 1 d . . . . .
H19 H -0.031514 0.555273 0.685866 0.083 Uiso 1 1 calc R . . . .


_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 C13 1.3656(17) . ?
O1 C1 1.3626(16) . ?
O2 N4 1.2499(16) . ?
O3 N4 1.2686(16) . ?
N4 C12 1.3797(18) . ?
N3 H3 0.8600 . ?
N3 C13 1.3089(18) . ?
N3 C14 1.4528(19) . ?
N1 N2 1.3730(16) . ?
N1 C1 1.3540(18) . ?
N1 C4 1.4240(17) . ?
N2 C3 1.3307(19) . ?
C13 C12 1.399(2) . ?
C15 C11 1.5299(19) . ?
C15 C16 1.3765(19) . ?
C15 C20 1.3844(19) . ?
C2 C1 1.3452(19) . ?
C2 C11 1.5029(19) . ?
C2 C3 1.410(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.511(2) . ?
C4 C9 1.385(2) . ?
C4 C5 1.378(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(2) . ?
C3 C10 1.488(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.377(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C19 H19 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
C1 O1 C13 115.11(11) . . ?
O2 N4 O3 120.15(12) . . ?
O2 N4 C12 118.36(13) . . ?
O3 N4 C12 121.49(13) . . ?
C13 N3 H3 117.9 . . ?
C13 N3 C14 124.17(13) . . ?
C14 N3 H3 117.9 . . ?
N2 N1 C4 121.78(11) . . ?
C1 N1 N2 108.89(11) . . ?
C1 N1 C4 128.44(12) . . ?
C3 N2 N1 105.30(11) . . ?
O1 C13 C12 121.11(13) . . ?
N3 C13 O1 110.15(13) . . ?
N3 C13 C12 128.74(13) . . ?
C16 C15 C11 119.75(12) . . ?
C16 C15 C20 118.00(13) . . ?
C20 C15 C11 122.25(13) . . ?
C1 C2 C11 121.30(13) . . ?
C1 C2 C3 103.38(12) . . ?
C3 C2 C11 135.31(13) . . ?
N1 C1 O1 121.06(12) . . ?
C2 C1 O1 128.32(13) . . ?
C2 C1 N1 110.55(12) . . ?
C15 C11 H11 108.5 . . ?
C2 C11 C15 112.21(11) . . ?
C2 C11 H11 108.5 . . ?
C2 C11 C12 106.97(11) . . ?
C12 C11 C15 112.10(11) . . ?
C12 C11 H11 108.5 . . ?
C9 C4 N1 119.63(12) . . ?
C5 C4 N1 120.10(13) . . ?
C5 C4 C9 120.24(14) . . ?
N4 C12 C13 118.52(13) . . ?
N4 C12 C11 116.16(12) . . ?
C13 C12 C11 125.32(12) . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.35(14) . . ?
C17 C16 H16 119.3 . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.63(14) . . ?
C8 C9 H9 120.2 . . ?
N2 C3 C2 111.87(12) . . ?
N2 C3 C10 121.11(14) . . ?
C2 C3 C10 127.03(14) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.38(15) . . ?
C6 C5 H5 120.3 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.29(15) . . ?
C7 C8 H8 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.16(15) . . ?
C18 C17 H17 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.66(15) . . ?
C19 C20 H20 119.7 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.51(15) . . ?
C19 C18 H18 120.2 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 119.95(15) . . ?
C6 C7 H7 120.0 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.47(15) . . ?
C7 C6 H6 119.8 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.31(16) . . ?
C18 C19 H19 119.8 . . ?

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
_geom_hbond_publ_flag
N3 H3 O3 0.86 1.97 2.5892(17) 128.0 . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.680
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_sub-musa-ca1
_database_code_depnum_ccdc_archive 'CCDC 1901105'
loop_
_audit_author_name
_audit_author_address
'Dr. Md. Musawwer Khan '
;Aligarh Muslim University 
India
;
_audit_update_record             
;
2019-03-05 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 Cl N2 O5'
_chemical_formula_sum            'C19 H13 Cl N2 O5'
_chemical_formula_weight         384.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5412(2)
_cell_length_b                   13.1791(3)
_cell_length_c                   14.8906(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.973(2)
_cell_angle_gamma                90
_cell_volume                     1663.77(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3930
_cell_measurement_theta_min      3.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             792
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19405
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.422
_diffrn_reflns_theta_min         3.297
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  -3.00   0.50   10.00    --   -9.95 125.00 -60.00   68
  2  ω    -58.00 -33.00   0.50   10.00    --   -9.95 125.00 -30.00   50
  3  ω    -58.00 -29.00   0.50   10.00    --   -9.95 125.00 -90.00   58
  4  ω      8.00  34.00   0.50   10.00    --   -9.95  77.00-150.00   52
  5  ω    -10.00  40.00   0.50   10.00    --   10.22 -99.00-120.00  100
  6  ω    -46.00  -8.00   0.50   10.00    --   10.22 -38.00 -60.00   76
  7  ω    -60.00  22.00   0.50   10.00    --   10.22 -19.00 150.00  164
  8  ω     22.00  56.00   0.50   10.00    --   10.22-125.00-180.00   68
  9  ω    -33.00   1.00   0.50   10.00    --   10.22 120.00  93.37   68
 10  ω     16.00  41.00   0.50   10.00    --   10.22 -99.00  90.00   50
 11  ω    -13.00  38.00   0.50   10.00    --   10.22 -99.00 -60.00  102
 12  ω    -17.00   8.00   0.50   10.00    --   10.22 -99.00-180.00   50
 13  ω     11.00  43.00   0.50   10.00    --   10.22 -99.00-180.00   64
 14  ω     13.00  71.00   0.50   10.00    --   10.22  38.00  90.00  116
 15  ω    -33.00  -4.00   0.50   10.00    --   10.22 126.00-112.08   58
 16  ω    -59.00  18.00   0.50   10.00    --   10.22 -19.00  60.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0090740000
_diffrn_orient_matrix_UB_12      0.0386550000
_diffrn_orient_matrix_UB_13      0.0321427000
_diffrn_orient_matrix_UB_21      -0.0044823000
_diffrn_orient_matrix_UB_22      0.0369498000
_diffrn_orient_matrix_UB_23      -0.0348321000
_diffrn_orient_matrix_UB_31      -0.0830251000
_diffrn_orient_matrix_UB_32      -0.0062513000
_diffrn_orient_matrix_UB_33      -0.0074901000
_diffrn_oxdiff_ac3_digest_frames 
;
01e41ef7774197afb22a122243869f49f900025efc4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
019a66b910da186bb4c5afa7c3513a718b5f5d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2774
_reflns_number_total             3592
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1041
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C7(H7), C13(H13), C4(H4), C6(H6), C14(H14), C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.06607(6) 1.06185(4) 0.31546(4) 0.06921(18) Uani 1 1 d . . . . .
O3 O 0.39773(12) 0.56282(8) 0.35504(7) 0.0424(3) Uani 1 1 d . . . . .
O4 O 0.21135(14) 0.55767(9) 0.59684(8) 0.0546(3) Uani 1 1 d . . . . .
O2 O 0.69954(14) 0.78914(10) 0.30078(9) 0.0606(3) Uani 1 1 d . . . . .
O1 O 0.64180(14) 0.87283(9) 0.41866(9) 0.0598(3) Uani 1 1 d . . . . .
N2 N 0.56448(15) 0.61519(11) 0.26166(9) 0.0470(3) Uani 1 1 d . . . . .
H2 H 0.629801 0.658419 0.244105 0.056 Uiso 1 1 calc R . . . .
O5 O 0.29345(19) 0.71397(11) 0.62894(9) 0.0742(4) Uani 1 1 d . . . . .
N1 N 0.62324(15) 0.79803(10) 0.36760(10) 0.0461(3) Uani 1 1 d . . . . .
C9 C 0.49690(17) 0.63777(12) 0.33397(10) 0.0382(3) Uani 1 1 d . . . . .
C11 C 0.33529(17) 0.56714(11) 0.43562(10) 0.0373(3) Uani 1 1 d . . . . .
C8 C 0.51642(17) 0.72398(11) 0.38683(10) 0.0389(3) Uani 1 1 d . . . . .
C2 C 0.28743(17) 0.82503(11) 0.42567(10) 0.0374(3) Uani 1 1 d . . . . .
C1 C 0.41515(17) 0.74781(11) 0.45926(10) 0.0397(4) Uani 1 1 d . . . . .
H1 H 0.481543 0.776569 0.511361 0.048 Uiso 1 1 calc R . . . .
C12 C 0.25792(17) 0.47527(12) 0.45827(11) 0.0408(4) Uani 1 1 d . . . . .
C19 C 0.34423(18) 0.64994(12) 0.48767(10) 0.0392(3) Uani 1 1 d . . . . .
C3 C 0.26592(18) 0.91249(12) 0.47394(11) 0.0443(4) Uani 1 1 d . . . . .
H3 H 0.326277 0.922926 0.529465 0.053 Uiso 1 1 calc R . . . .
C5 C 0.06680(18) 0.96869(12) 0.35895(12) 0.0444(4) Uani 1 1 d . . . . .
C17 C 0.19485(18) 0.47536(13) 0.53980(11) 0.0457(4) Uani 1 1 d . . . . .
C7 C 0.19399(18) 0.81050(12) 0.34356(11) 0.0446(4) Uani 1 1 d . . . . .
H7 H 0.206058 0.751691 0.310576 0.053 Uiso 1 1 calc R . . . .
C13 C 0.23922(19) 0.38903(13) 0.40356(12) 0.0489(4) Uani 1 1 d . . . . .
H13 H 0.281348 0.387532 0.348843 0.059 Uiso 1 1 calc R . . . .
C4 C 0.15634(19) 0.98464(13) 0.44112(12) 0.0478(4) Uani 1 1 d . . . . .
H4 H 0.143137 1.043299 0.474102 0.057 Uiso 1 1 calc R . . . .
C6 C 0.08361(19) 0.88175(13) 0.31005(11) 0.0484(4) Uani 1 1 d . . . . .
H6 H 0.021455 0.871065 0.255135 0.058 Uiso 1 1 calc R . . . .
C18 C 0.2837(2) 0.64644(14) 0.57453(11) 0.0512(4) Uani 1 1 d . . . . .
C10 C 0.5367(2) 0.52235(15) 0.20927(12) 0.0585(5) Uani 1 1 d . . . . .
H10A H 0.583450 0.528243 0.154047 0.088 Uiso 1 1 calc GR . . . .
H10B H 0.425193 0.511516 0.195428 0.088 Uiso 1 1 calc GR . . . .
H10C H 0.582972 0.466042 0.243752 0.088 Uiso 1 1 calc GR . . . .
C14 C 0.1587(2) 0.30635(14) 0.43048(15) 0.0597(5) Uani 1 1 d . . . . .
H14 H 0.146274 0.248976 0.393948 0.072 Uiso 1 1 calc R . . . .
C16 C 0.1129(2) 0.39185(15) 0.56716(14) 0.0572(5) Uani 1 1 d . . . . .
H16 H 0.070626 0.392648 0.621829 0.069 Uiso 1 1 calc R . . . .
C15 C 0.0959(2) 0.30840(15) 0.51195(15) 0.0629(5) Uani 1 1 d . . . . .
H15 H 0.041214 0.252174 0.529485 0.076 Uiso 1 1 calc R . . . .


_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
Cl1 C5 1.7424(16) . ?
O3 C9 1.3624(17) . ?
O3 C11 1.3721(17) . ?
O4 C17 1.374(2) . ?
O4 C18 1.382(2) . ?
O2 N1 1.2594(18) . ?
O1 N1 1.2432(18) . ?
N2 H2 0.8600 . ?
N2 C9 1.316(2) . ?
N2 C10 1.455(2) . ?
O5 C18 1.200(2) . ?
N1 C8 1.3893(19) . ?
C9 C8 1.381(2) . ?
C11 C12 1.439(2) . ?
C11 C19 1.335(2) . ?
C8 C1 1.496(2) . ?
C2 C1 1.531(2) . ?
C2 C3 1.382(2) . ?
C2 C7 1.390(2) . ?
C1 H1 0.9800 . ?
C1 C19 1.507(2) . ?
C12 C17 1.387(2) . ?
C12 C13 1.396(2) . ?
C19 C18 1.451(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(2) . ?
C5 C4 1.378(2) . ?
C5 C6 1.374(2) . ?
C17 C16 1.391(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(2) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.370(3) . ?
C15 H15 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
C9 O3 C11 119.32(12) . . ?
C17 O4 C18 122.33(13) . . ?
C9 N2 H2 117.6 . . ?
C9 N2 C10 124.72(14) . . ?
C10 N2 H2 117.6 . . ?
O2 N1 C8 120.88(14) . . ?
O1 N1 O2 121.14(14) . . ?
O1 N1 C8 117.98(14) . . ?
O3 C9 C8 120.06(13) . . ?
N2 C9 O3 111.78(13) . . ?
N2 C9 C8 128.16(14) . . ?
O3 C11 C12 114.10(13) . . ?
C19 C11 O3 122.72(13) . . ?
C19 C11 C12 123.17(14) . . ?
N1 C8 C1 116.93(13) . . ?
C9 C8 N1 119.84(14) . . ?
C9 C8 C1 122.92(13) . . ?
C3 C2 C1 121.26(13) . . ?
C3 C2 C7 118.29(14) . . ?
C7 C2 C1 120.41(13) . . ?
C8 C1 C2 110.83(12) . . ?
C8 C1 H1 108.8 . . ?
C8 C1 C19 108.06(12) . . ?
C2 C1 H1 108.8 . . ?
C19 C1 C2 111.46(12) . . ?
C19 C1 H1 108.8 . . ?
C17 C12 C11 116.28(15) . . ?
C17 C12 C13 118.85(15) . . ?
C13 C12 C11 124.85(15) . . ?
C11 C19 C1 122.21(13) . . ?
C11 C19 C18 119.34(15) . . ?
C18 C19 C1 118.45(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.15(15) . . ?
C4 C3 H3 119.4 . . ?
C4 C5 Cl1 119.26(13) . . ?
C6 C5 Cl1 119.72(13) . . ?
C6 C5 C4 121.01(15) . . ?
O4 C17 C12 121.34(14) . . ?
O4 C17 C16 117.44(16) . . ?
C12 C17 C16 121.21(17) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.22(15) . . ?
C6 C7 H7 119.4 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.08(18) . . ?
C14 C13 H13 120.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.22(15) . . ?
C5 C4 H4 120.4 . . ?
C5 C6 C7 119.10(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
O4 C18 C19 117.34(15) . . ?
O5 C18 O4 117.52(15) . . ?
O5 C18 C19 125.13(17) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.06(19) . . ?
C15 C14 H14 120.0 . . ?
C17 C16 H16 120.7 . . ?
C15 C16 C17 118.67(18) . . ?
C15 C16 H16 120.7 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.13(17) . . ?
C16 C15 H15 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.671
