# 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_mb-2-29-03-14
_database_code_depnum_ccdc_archive 'CCDC 1906333'
loop_
_audit_author_name
_audit_author_address
'Vishal Agarwal'
;Pondicherry University
India
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            'Heptacyclic Benzo[a]phenazinone'
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H27 Br N2 O4'
_chemical_formula_sum            'C35 H27 Br N2 O4'
_chemical_formula_weight         630.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H14 N2 Cl2'
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'
Br Br -0.2901 2.4595 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.8736(11)
_cell_length_b                   11.2191(11)
_cell_length_c                   12.8583(13)
_cell_angle_alpha                70.525(9)
_cell_angle_beta                 84.720(8)
_cell_angle_gamma                84.754(8)
_cell_volume                     1469.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1481
_cell_measurement_theta_min      3.7640
_exptl_absorpt_coefficient_mu    1.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15946
_diffrn_reflns_theta_full        29.21
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.77
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   37.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00    4.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -57.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00   26.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -19.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega  -22.00   25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega  -93.00  -35.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega    9.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366 -144.0000  107.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000  -60.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0292237000
_diffrn_orient_matrix_UB_12      0.0512800000
_diffrn_orient_matrix_UB_13      -0.0407913000
_diffrn_orient_matrix_UB_21      0.0300849000
_diffrn_orient_matrix_UB_22      -0.0222687000
_diffrn_orient_matrix_UB_23      -0.0419685000
_diffrn_orient_matrix_UB_31      -0.0505016000
_diffrn_orient_matrix_UB_32      -0.0372863000
_diffrn_orient_matrix_UB_33      0.0035988000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3538
_reflns_number_total             6803
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0752P)²+0.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1773
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.91543(5) 0.45950(7) 0.30022(5) 0.1286(3) Uani 1 d . . .
N1 N 0.51799(19) 0.0510(2) 0.25195(18) 0.0375(5) Uani 1 d . . .
N2 N 0.3566(2) 0.0196(2) 0.43963(19) 0.0446(6) Uani 1 d . . .
C3 C 0.4678(2) 0.1562(3) 0.2777(2) 0.0372(6) Uani 1 d . . .
C4 C 0.3816(2) 0.1322(3) 0.3757(2) 0.0386(6) Uani 1 d . . .
C5 C 0.3194(2) 0.2411(3) 0.4028(2) 0.0416(7) Uani 1 d . . .
C6 C 0.4945(2) 0.2774(3) 0.2147(2) 0.0412(7) Uani 1 d . . .
C7 C 0.4120(2) -0.0838(3) 0.4142(2) 0.0428(7) Uani 1 d . . .
O8 O 0.77267(18) 0.2476(2) -0.03731(17) 0.0555(6) Uani 1 d . . .
C9 C 0.5733(2) 0.3036(3) 0.1090(2) 0.0409(6) Uani 1 d . . .
H9 H 0.5357 0.3796 0.0558 0.049 Uiso 1 calc . . R
C10 C 0.4348(3) 0.3845(3) 0.2409(3) 0.0480(7) Uani 1 d . . .
C11 C 0.3441(2) 0.3633(3) 0.3363(2) 0.0438(7) Uani 1 d . . .
C12 C 0.6007(2) 0.0656(3) 0.1509(2) 0.0388(6) Uani 1 d . . .
H12 H 0.5800 0.0008 0.1208 0.047 Uiso 1 calc . . R
C13 C 0.4920(2) -0.0705(3) 0.3193(2) 0.0405(6) Uani 1 d . . .
O14 O 0.4592(2) 0.4937(2) 0.1839(2) 0.0789(8) Uani 1 d . . .
C15 C 0.3846(3) -0.2044(3) 0.4829(3) 0.0540(8) Uani 1 d . . .
H15 H 0.3316 -0.2133 0.5457 0.065 Uiso 1 calc . . R
O16 O 0.3924(2) 0.0932(2) 0.0365(2) 0.0756(8) Uani 1 d . . .
O17 O 0.37667(19) 0.2996(2) 0.0001(2) 0.0754(8) Uani 1 d . . .
C18 C 0.5674(2) 0.1944(3) 0.0640(2) 0.0394(6) Uani 1 d . . .
C19 C 0.5422(3) -0.1791(3) 0.2973(3) 0.0513(8) Uani 1 d . . .
H19 H 0.5958 -0.1719 0.2351 0.062 Uiso 1 calc . . R
C20 C 0.4366(2) 0.1888(3) 0.0321(2) 0.0437(7) Uani 1 d . . .
C21 C 0.7793(3) 0.0596(3) 0.2672(2) 0.0445(7) Uani 1 d . . .
H21 H 0.7260 0.0943 0.3119 0.053 Uiso 1 calc . . R
C22 C 0.7348(2) 0.0349(3) 0.1799(2) 0.0393(6) Uani 1 d . . .
C23 C 0.6481(2) 0.2202(3) -0.0439(2) 0.0461(7) Uani 1 d . . .
H23A H 0.6503 0.1469 -0.0681 0.055 Uiso 1 calc . . R
H23B H 0.6095 0.2913 -0.0998 0.055 Uiso 1 calc . . R
C24 C 0.7963(3) 0.3014(3) 0.0388(2) 0.0479(7) Uani 1 d . . .
C25 C 0.7448(3) 0.3756(3) 0.1911(3) 0.0561(8) Uani 1 d . . .
H25 H 0.6866 0.3946 0.2419 0.067 Uiso 1 calc . . R
C26 C 0.5128(3) -0.2966(3) 0.3672(3) 0.0606(9) Uani 1 d . . .
H26 H 0.5464 -0.3686 0.3518 0.073 Uiso 1 calc . . R
C27 C 0.7069(2) 0.3280(3) 0.1130(2) 0.0438(7) Uani 1 d . . .
C28 C 0.2826(3) 0.4657(3) 0.3617(3) 0.0573(8) Uani 1 d . . .
H28 H 0.2982 0.5478 0.3170 0.069 Uiso 1 calc . . R
C29 C 0.9033(3) 0.0330(3) 0.2887(3) 0.0558(8) Uani 1 d . . .
H29 H 0.9322 0.0527 0.3465 0.067 Uiso 1 calc . . R
C30 C 0.8155(3) -0.0219(3) 0.1184(3) 0.0512(8) Uani 1 d . . .
H30 H 0.7867 -0.0419 0.0607 0.061 Uiso 1 calc . . R
C31 C 0.4334(3) -0.3094(3) 0.4607(3) 0.0586(9) Uani 1 d . . .
H31 H 0.4139 -0.3894 0.5076 0.070 Uiso 1 calc . . R
C32 C 0.2346(3) 0.2238(3) 0.4931(3) 0.0570(8) Uani 1 d . . .
H32 H 0.2168 0.1423 0.5377 0.068 Uiso 1 calc . . R
C33 C 0.1772(3) 0.3261(4) 0.5168(3) 0.0670(10) Uani 1 d . . .
H33 H 0.1218 0.3134 0.5785 0.080 Uiso 1 calc . . R
C34 C 0.9387(3) -0.0495(3) 0.1417(3) 0.0623(9) Uani 1 d . . .
H34 H 0.9915 -0.0875 0.0991 0.075 Uiso 1 calc . . R
C35 C 0.2002(3) 0.4472(4) 0.4509(3) 0.0663(10) Uani 1 d . . .
H35 H 0.1596 0.5162 0.4672 0.080 Uiso 1 calc . . R
C36 C 0.8668(3) 0.3946(4) 0.1939(3) 0.0661(10) Uani 1 d . . .
C37 C 0.9845(3) -0.0216(3) 0.2270(3) 0.0593(9) Uani 1 d . . .
C38 C 0.9192(3) 0.3229(3) 0.0415(3) 0.0612(9) Uani 1 d . . .
H38 H 0.9779 0.3058 -0.0098 0.073 Uiso 1 calc . . R
C39 C 0.9546(3) 0.3690(4) 0.1190(3) 0.0698(10) Uani 1 d . . .
H39 H 1.0372 0.3830 0.1211 0.084 Uiso 1 calc . . R
C40 C 1.1200(3) -0.0529(4) 0.2502(4) 0.0828(12) Uani 1 d . . .
H40A H 1.1703 -0.0204 0.1817 0.099 Uiso 1 calc . . R
H40B H 1.1407 -0.0107 0.3004 0.099 Uiso 1 calc . . R
C41 C 0.2521(3) 0.3034(4) -0.0316(4) 0.0921(14) Uani 1 d . . .
H41A H 0.2547 0.2916 -0.1024 0.138 Uiso 1 calc . . GR
H41B H 0.2104 0.3839 -0.0360 0.138 Uiso 1 calc . . GR
H41C H 0.2083 0.2371 0.0224 0.138 Uiso 1 calc . . GR
C14 C 1.1502(4) -0.1889(5) 0.2986(4) 0.1064(16) Uani 1 d . . .
H14A H 1.1260 -0.2318 0.2512 0.160 Uiso 1 calc . . GR
H14B H 1.1068 -0.2202 0.3698 0.160 Uiso 1 calc . . GR
H14C H 1.2377 -0.2040 0.3066 0.160 Uiso 1 calc . . GR


_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
Br1 C36 1.883(3) . ?
N1 C3 1.382(3) . ?
N1 C12 1.482(3) . ?
N1 C13 1.388(3) . ?
N2 C4 1.294(3) . ?
N2 C7 1.379(4) . ?
C3 C4 1.463(4) . ?
C3 C6 1.373(4) . ?
C4 C5 1.469(4) . ?
C5 C11 1.388(4) . ?
C5 C32 1.386(4) . ?
C6 C9 1.494(4) . ?
C6 C10 1.437(4) . ?
C7 C13 1.406(4) . ?
C7 C15 1.389(4) . ?
O8 C23 1.432(3) . ?
O8 C24 1.362(4) . ?
C9 C18 1.529(4) . ?
C9 C27 1.511(4) . ?
C10 C11 1.470(4) . ?
C10 O14 1.238(3) . ?
C11 C28 1.394(4) . ?
C12 C18 1.539(4) . ?
C12 C22 1.519(4) . ?
C13 C19 1.393(4) . ?
C15 C31 1.354(4) . ?
O16 C20 1.197(4) . ?
O17 C20 1.304(3) . ?
O17 C41 1.444(4) . ?
C18 C20 1.529(4) . ?
C18 C23 1.527(4) . ?
C19 C26 1.373(4) . ?
C21 C22 1.381(4) . ?
C21 C29 1.386(4) . ?
C22 C30 1.381(4) . ?
C24 C27 1.382(4) . ?
C24 C38 1.385(4) . ?
C25 C27 1.392(4) . ?
C25 C36 1.369(5) . ?
C26 C31 1.388(5) . ?
C28 C35 1.360(4) . ?
C29 C37 1.372(5) . ?
C30 C34 1.384(4) . ?
C32 C33 1.366(4) . ?
C33 C35 1.372(5) . ?
C34 C37 1.380(5) . ?
C36 C39 1.373(5) . ?
C37 C40 1.516(4) . ?
C38 C39 1.363(5) . ?
C40 C14 1.461(6) . ?

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
C3 N1 C12 120.5(2) . . ?
C3 N1 C13 121.2(2) . . ?
C13 N1 C12 118.3(2) . . ?
C4 N2 C7 119.0(2) . . ?
N1 C3 C4 116.4(2) . . ?
C6 C3 N1 122.6(2) . . ?
C6 C3 C4 121.0(2) . . ?
N2 C4 C3 123.2(3) . . ?
N2 C4 C5 118.2(2) . . ?
C3 C4 C5 118.6(2) . . ?
C11 C5 C4 119.8(2) . . ?
C32 C5 C4 121.0(3) . . ?
C32 C5 C11 119.2(3) . . ?
C3 C6 C9 121.4(2) . . ?
C3 C6 C10 120.8(2) . . ?
C10 C6 C9 117.4(2) . . ?
N2 C7 C13 122.0(3) . . ?
N2 C7 C15 118.8(3) . . ?
C15 C7 C13 119.2(3) . . ?
C24 O8 C23 118.8(2) . . ?
C6 C9 C18 108.8(2) . . ?
C6 C9 C27 116.9(2) . . ?
C27 C9 C18 109.6(2) . . ?
C6 C10 C11 119.3(3) . . ?
O14 C10 C6 120.6(3) . . ?
O14 C10 C11 120.1(3) . . ?
C5 C11 C10 120.4(3) . . ?
C5 C11 C28 119.2(3) . . ?
C28 C11 C10 120.3(3) . . ?
N1 C12 C18 109.0(2) . . ?
N1 C12 C22 110.5(2) . . ?
C22 C12 C18 117.8(2) . . ?
N1 C13 C7 118.1(3) . . ?
N1 C13 C19 123.0(3) . . ?
C19 C13 C7 118.9(3) . . ?
C31 C15 C7 121.5(3) . . ?
C20 O17 C41 116.7(3) . . ?
C9 C18 C12 111.6(2) . . ?
C20 C18 C9 110.6(2) . . ?
C20 C18 C12 106.8(2) . . ?
C23 C18 C9 109.1(2) . . ?
C23 C18 C12 113.5(2) . . ?
C23 C18 C20 105.0(2) . . ?
C26 C19 C13 120.1(3) . . ?
O16 C20 O17 122.9(3) . . ?
O16 C20 C18 124.1(3) . . ?
O17 C20 C18 112.9(3) . . ?
C22 C21 C29 120.3(3) . . ?
C21 C22 C12 122.4(2) . . ?
C21 C22 C30 118.2(2) . . ?
C30 C22 C12 119.3(2) . . ?
O8 C23 C18 114.9(2) . . ?
O8 C24 C27 123.6(2) . . ?
O8 C24 C38 115.4(3) . . ?
C27 C24 C38 120.9(3) . . ?
C36 C25 C27 120.6(3) . . ?
C19 C26 C31 120.8(3) . . ?
C24 C27 C9 120.2(3) . . ?
C24 C27 C25 117.8(3) . . ?
C25 C27 C9 122.0(3) . . ?
C35 C28 C11 120.9(3) . . ?
C37 C29 C21 121.8(3) . . ?
C22 C30 C34 120.7(3) . . ?
C15 C31 C26 119.5(3) . . ?
C33 C32 C5 120.3(3) . . ?
C32 C33 C35 120.9(3) . . ?
C37 C34 C30 121.3(3) . . ?
C28 C35 C33 119.5(3) . . ?
C25 C36 Br1 119.7(3) . . ?
C25 C36 C39 121.0(3) . . ?
C39 C36 Br1 119.3(2) . . ?
C29 C37 C34 117.6(3) . . ?
C29 C37 C40 122.5(3) . . ?
C34 C37 C40 119.9(3) . . ?
C39 C38 C24 120.4(3) . . ?
C38 C39 C36 119.2(3) . . ?
C14 C40 C37 112.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_mb-4-29-03-14
_database_code_depnum_ccdc_archive 'CCDC 1906667'
loop_
_audit_author_name
_audit_author_address
'Vishal Agarwal'
;Pondicherry University
India
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_mb-4-29-03-14       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.654 Why?
RESPONSE: Due to Instrument issue, data is incomplete which results in A alert.
;
# Added during the CSD deposition process: Friday 29 March 2019 06:45 PM
# end Validation Reply Form

_audit_creation_date             2019-03-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H19 N2 O6'
_chemical_formula_sum            'C31 H25 N2 O6'
_chemical_formula_weight         521.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H14 N2 O2'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.2139(7)
_cell_length_b                   10.5529(9)
_cell_length_c                   19.644(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.522(7)
_cell_angle_gamma                90.00
_cell_volume                     2515.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0062
_cell_measurement_theta_min      3.9037
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7487
_diffrn_reflns_theta_full        29.07
_diffrn_reflns_theta_max         29.07
_diffrn_reflns_theta_min         3.91
_diffrn_ambient_temperature      '293 (2)'
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.654
_diffrn_measured_fraction_theta_max 0.654
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   27.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   -4.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00  -55.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0076937000
_diffrn_orient_matrix_UB_12      -0.0658671000
_diffrn_orient_matrix_UB_13      -0.0060810000
_diffrn_orient_matrix_UB_21      -0.0517417000
_diffrn_orient_matrix_UB_22      0.0125788000
_diffrn_orient_matrix_UB_23      -0.0190833000
_diffrn_orient_matrix_UB_31      0.0262472000
_diffrn_orient_matrix_UB_32      0.0054074000
_diffrn_orient_matrix_UB_33      -0.0302310000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2763
_reflns_number_total             4410
_reflns_odcompleteness_completeness 77.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.074
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C2B)=Sof(H29)=Sof(H2Ba)=Sof(H2Bb)=Sof(H2Bc)=1-FVAR(1)
 Sof(C2A)=Sof(H29a)=Sof(H2Aa)=Sof(H2Ab)=Sof(H2Ac)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C12(H12), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C38(H38a,H38b)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
 C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C29(H29a), C29(H29)
3.d Idealised Me refined as rotating group:
 C34(H34a,H34b,H34c), C2A(H2Aa,H2Ab,H2Ac), C2B(H2Ba,H2Bb,H2Bc)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.34146(12) 0.12211(16) 0.18524(10) 0.0478(5) Uani 1 d . . .
O2 O 0.56235(14) 0.5912(2) 0.19737(10) 0.0615(6) Uani 1 d . . .
N3 N 0.29788(14) 0.28973(18) 0.10573(10) 0.0377(5) Uani 1 d . . .
C4 C 0.35884(15) 0.4013(2) 0.10066(12) 0.0325(6) Uani 1 d . . .
N5 N 0.28241(15) 0.4263(2) -0.01833(11) 0.0439(5) Uani 1 d . . .
C6 C 0.42807(16) 0.4438(2) 0.15540(12) 0.0348(6) Uani 1 d . . .
C7 C 0.39792(17) 0.5922(2) 0.03138(14) 0.0384(6) Uani 1 d . . .
C8 C 0.34293(16) 0.4679(2) 0.03606(13) 0.0357(6) Uani 1 d . . .
C9 C 0.47042(18) 0.6346(2) 0.08768(14) 0.0413(7) Uani 1 d . . .
O10 O 0.09569(13) 0.29904(19) 0.16135(10) 0.0603(6) Uani 1 d A . .
C11 C 0.49146(17) 0.5595(2) 0.15064(14) 0.0407(6) Uani 1 d . . .
C12 C 0.43637(17) 0.3702(2) 0.22055(13) 0.0382(6) Uani 1 d . . .
H12 H 0.4678 0.4228 0.2590 0.046 Uiso 1 calc . . R
C13 C 0.15919(19) 0.1990(3) 0.17476(14) 0.0478(7) Uani 1 d . . .
C14 C 0.23947(18) 0.3042(3) -0.01525(14) 0.0442(7) Uani 1 d . . .
O15 O 0.12918(16) 0.0947(2) 0.18703(13) 0.0766(7) Uani 1 d . . .
C16 C 0.24924(17) 0.2330(2) 0.04511(14) 0.0414(6) Uani 1 d . . .
C17 C 0.31708(18) 0.3333(3) 0.22957(13) 0.0426(6) Uani 1 d . . .
H17 H 0.2713 0.4090 0.2206 0.051 Uiso 1 calc . . R
O18 O 0.38538(16) 0.2798(2) 0.34326(10) 0.0685(7) Uani 1 d . . .
C19 C 0.3823(2) 0.6645(3) -0.02770(15) 0.0528(7) Uani 1 d . . .
H19 H 0.3361 0.6353 -0.0653 0.063 Uiso 1 calc . . R
C20 C 0.28153(17) 0.2372(2) 0.17340(13) 0.0386(6) Uani 1 d . . .
C21 C 0.50493(17) 0.2508(3) 0.21565(13) 0.0412(6) Uani 1 d . . .
C22 C 0.45537(18) 0.1355(2) 0.19836(13) 0.0430(6) Uani 1 d . . .
C23 C 0.5059(3) 0.8222(3) 0.0241(2) 0.0675(10) Uani 1 d . . .
H23 H 0.5416 0.8996 0.0216 0.081 Uiso 1 calc . . R
C24 C 0.2965(2) 0.2826(3) 0.29889(15) 0.0547(8) Uani 1 d . . .
C25 C 0.5240(2) 0.7509(2) 0.08233(17) 0.0550(8) Uani 1 d . . .
H25 H 0.5725 0.7800 0.1189 0.066 Uiso 1 calc . . R
C26 C 0.61994(19) 0.2536(3) 0.22857(13) 0.0543(8) Uani 1 d . . .
H26 H 0.6558 0.3296 0.2402 0.065 Uiso 1 calc . . R
C27 C 0.4350(3) 0.7803(3) -0.03108(19) 0.0654(9) Uani 1 d . . .
H27 H 0.4227 0.8296 -0.0704 0.079 Uiso 1 calc . . R
O28 O 0.20727(18) 0.2527(3) 0.31217(12) 0.1125(12) Uani 1 d . . .
C29 C -0.0222(2) 0.2803(4) 0.16759(19) 0.0830(12) Uani 1 d . . .
C30 C 0.6811(2) 0.1427(4) 0.22409(16) 0.0711(10) Uani 1 d . . .
H30 H 0.7575 0.1448 0.2328 0.085 Uiso 1 calc . . R
C31 C 0.5152(2) 0.0251(3) 0.19353(15) 0.0575(8) Uani 1 d . . .
H31 H 0.4798 -0.0510 0.1816 0.069 Uiso 1 calc . . R
C32 C 0.6279(2) 0.0302(4) 0.20668(18) 0.0710(9) Uani 1 d . . .
H32 H 0.6689 -0.0434 0.2038 0.085 Uiso 1 calc . . R
C33 C 0.2142(2) 0.1062(3) 0.04186(17) 0.0606(8) Uani 1 d . . .
H33 H 0.2230 0.0559 0.0810 0.073 Uiso 1 calc . . R
C34 C 0.4042(4) 0.0989(4) 0.4141(2) 0.1035(14) Uani 1 d . . .
H34A H 0.3582 0.0530 0.3797 0.155 Uiso 1 calc . . GR
H34B H 0.3951 0.0650 0.4585 0.155 Uiso 1 calc . . GR
H34C H 0.4798 0.0909 0.4058 0.155 Uiso 1 calc . . GR
C35 C 0.1896(2) 0.2520(3) -0.07649(16) 0.0625(8) Uani 1 d . . .
H35 H 0.1816 0.3007 -0.1162 0.075 Uiso 1 calc . . R
C36 C 0.1525(3) 0.1293(4) -0.0783(2) 0.0812(11) Uani 1 d . . .
H36 H 0.1180 0.0953 -0.1189 0.097 Uiso 1 calc . . R
C37 C 0.1666(3) 0.0564(4) -0.0194(2) 0.0781(10) Uani 1 d . . .
H37 H 0.1436 -0.0277 -0.0212 0.094 Uiso 1 calc . . R
C38 C 0.3731(3) 0.2312(4) 0.41170(17) 0.0807(11) Uani 1 d . . .
H38A H 0.4199 0.2786 0.4459 0.097 Uiso 1 calc . . R
H38B H 0.2973 0.2404 0.4212 0.097 Uiso 1 calc . . R
C2A C -0.0731(5) 0.2475(9) 0.1034(4) 0.106(4) Uani 0.585(13) d A 1 .
C2B C -0.0908(6) 0.3718(14) 0.1372(6) 0.117(7) Uani 0.415(13) d A -1 .


_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 C20 1.424(3) . ?
O1 C22 1.393(3) . ?
O2 C11 1.234(3) . ?
N3 C4 1.403(3) . ?
N3 C16 1.403(3) . ?
N3 C20 1.474(3) . ?
C4 C6 1.366(3) . ?
C4 C8 1.444(3) . ?
N5 C8 1.304(3) . ?
N5 C14 1.395(3) . ?
C6 C11 1.454(3) . ?
C6 C12 1.491(3) . ?
C7 C8 1.481(3) . ?
C7 C9 1.409(4) . ?
C7 C19 1.384(4) . ?
C9 C11 1.467(4) . ?
C9 C25 1.400(3) . ?
O10 C13 1.319(3) . ?
O10 C29 1.472(3) . ?
C12 C17 1.538(3) . ?
C12 C21 1.522(3) . ?
C13 O15 1.194(3) . ?
C13 C20 1.551(3) . ?
C14 C16 1.397(4) . ?
C14 C35 1.398(4) . ?
C16 C33 1.404(4) . ?
C17 C20 1.525(4) . ?
C17 C24 1.510(4) . ?
O18 C24 1.313(3) . ?
O18 C38 1.462(4) . ?
C19 C27 1.386(4) . ?
C21 C22 1.384(4) . ?
C21 C26 1.399(3) . ?
C22 C31 1.385(4) . ?
C23 C25 1.366(4) . ?
C23 C27 1.381(5) . ?
C24 O28 1.192(3) . ?
C26 C30 1.397(4) . ?
C29 C2A 1.385(7) . ?
C29 C2B 1.370(11) . ?
C30 C32 1.378(5) . ?
C31 C32 1.371(4) . ?
C33 C37 1.380(4) . ?
C34 C38 1.446(5) . ?
C35 C36 1.371(5) . ?
C36 C37 1.384(5) . ?
C2A C2B 1.496(15) . ?

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
C22 O1 C20 115.31(18) . . ?
C4 N3 C20 120.45(19) . . ?
C16 N3 C4 118.3(2) . . ?
C16 N3 C20 121.15(19) . . ?
N3 C4 C8 116.8(2) . . ?
C6 C4 N3 120.4(2) . . ?
C6 C4 C8 122.8(2) . . ?
C8 N5 C14 117.1(2) . . ?
C4 C6 C11 120.7(2) . . ?
C4 C6 C12 118.7(2) . . ?
C11 C6 C12 120.5(2) . . ?
C9 C7 C8 118.8(2) . . ?
C19 C7 C8 121.3(2) . . ?
C19 C7 C9 119.8(2) . . ?
C4 C8 C7 117.9(2) . . ?
N5 C8 C4 124.3(2) . . ?
N5 C8 C7 117.8(2) . . ?
C7 C9 C11 121.6(2) . . ?
C25 C9 C7 118.5(3) . . ?
C25 C9 C11 119.9(3) . . ?
C13 O10 C29 115.8(2) . . ?
O2 C11 C6 120.9(3) . . ?
O2 C11 C9 121.4(2) . . ?
C6 C11 C9 117.7(2) . . ?
C6 C12 C17 104.94(18) . . ?
C6 C12 C21 111.18(18) . . ?
C21 C12 C17 109.5(2) . . ?
O10 C13 C20 109.5(2) . . ?
O15 C13 O10 126.3(2) . . ?
O15 C13 C20 124.2(2) . . ?
N5 C14 C16 122.5(2) . . ?
N5 C14 C35 117.1(3) . . ?
C16 C14 C35 120.3(3) . . ?
N3 C16 C33 122.9(2) . . ?
C14 C16 N3 118.6(2) . . ?
C14 C16 C33 118.5(2) . . ?
C20 C17 C12 106.30(18) . . ?
C24 C17 C12 116.8(2) . . ?
C24 C17 C20 110.8(2) . . ?
C24 O18 C38 117.1(2) . . ?
C7 C19 C27 120.4(3) . . ?
O1 C20 N3 110.37(18) . . ?
O1 C20 C13 104.70(18) . . ?
O1 C20 C17 110.5(2) . . ?
N3 C20 C13 110.04(19) . . ?
N3 C20 C17 110.24(19) . . ?
C17 C20 C13 110.87(19) . . ?
C22 C21 C12 120.97(19) . . ?
C22 C21 C26 117.7(2) . . ?
C26 C21 C12 121.3(2) . . ?
C21 C22 O1 122.3(2) . . ?
C31 C22 O1 115.2(2) . . ?
C31 C22 C21 122.5(2) . . ?
C25 C23 C27 120.5(3) . . ?
O18 C24 C17 113.4(2) . . ?
O28 C24 C17 122.7(3) . . ?
O28 C24 O18 123.8(3) . . ?
C23 C25 C9 120.9(3) . . ?
C30 C26 C21 120.3(3) . . ?
C23 C27 C19 119.9(3) . . ?
C2A C29 O10 107.5(4) . . ?
C2A C29 C2B 65.8(6) . . ?
C2B C29 O10 115.1(5) . . ?
C32 C30 C26 119.8(3) . . ?
C32 C31 C22 118.7(3) . . ?
C31 C32 C30 121.1(3) . . ?
C37 C33 C16 119.9(3) . . ?
C36 C35 C14 120.4(3) . . ?
C35 C36 C37 119.6(3) . . ?
C33 C37 C36 121.2(3) . . ?
C34 C38 O18 108.3(3) . . ?
C29 C2A C2B 56.6(5) . . ?
C29 C2B C2A 57.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
