# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ttt
_database_code_depnum_ccdc_archive 'CCDC 1946568'
loop_
_audit_author_name
_audit_author_address
'Sarasija Das'
;IISER Kolkata
India
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_audit_creation_date             2019-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H13 Br N2 O'
_chemical_formula_sum            'C24 H13 Br N2 O'
_chemical_formula_weight         425.27
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.495(4)
_cell_length_b                   15.107(7)
_cell_length_c                   12.403(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.99(2)
_cell_angle_gamma                90
_cell_volume                     1774.8(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.7220
_cell_measurement_theta_min      2.6300
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.49489
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull bluish green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.538
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2107
_reflns_number_total             4106
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.336
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      0.971
_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)+(0.0446P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.057
;
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
Br01 Br 0.22331(5) 0.71369(3) 0.73209(4) 0.0636(2) Uani 1 1 d . . . . .
O002 O 0.5968(3) 0.38850(18) 0.6521(2) 0.0556(8) Uani 1 1 d . . . . .
N003 N 0.2396(3) 0.44899(19) 0.4565(2) 0.0351(7) Uani 1 1 d . . . . .
N004 N 0.1099(3) 0.61373(19) 0.5086(3) 0.0413(8) Uani 1 1 d . . . . .
C005 C 0.2880(4) 0.4998(2) 0.5413(3) 0.0334(8) Uani 1 1 d . . . . .
C006 C 0.2184(4) 0.5814(2) 0.5651(3) 0.0364(9) Uani 1 1 d . . . . .
C007 C 0.2938(4) 0.3615(2) 0.4540(3) 0.0378(9) Uani 1 1 d . . . . .
C008 C 0.0727(4) 0.5671(2) 0.4138(3) 0.0388(9) Uani 1 1 d . . . . .
C009 C 0.3976(4) 0.4824(2) 0.6164(3) 0.0369(9) Uani 1 1 d . . . . .
C00A C 0.1383(4) 0.4884(2) 0.3824(3) 0.0357(9) Uani 1 1 d . . . . .
C00B C 0.4827(4) 0.4060(2) 0.6034(3) 0.0402(9) Uani 1 1 d . . . . .
C00C C 0.4159(4) 0.3426(2) 0.5213(3) 0.0386(9) Uani 1 1 d . . . . .
C00D C 0.2924(4) 0.6143(2) 0.6617(3) 0.0415(10) Uani 1 1 d . . . . .
C00E C 0.4013(4) 0.5594(2) 0.6931(3) 0.0401(9) Uani 1 1 d . . . . .
C00F C 0.5054(4) 0.5723(3) 0.7847(3) 0.0442(10) Uani 1 1 d . . . . .
C00G C 0.2254(5) 0.2938(3) 0.3952(3) 0.0496(11) Uani 1 1 d . . . . .
H00G H 0.139724 0.304834 0.356571 0.059 Uiso 1 1 calc R . . . .
C00H C 0.4724(5) 0.2575(3) 0.5182(3) 0.0509(11) Uani 1 1 d . . . . .
H00H H 0.554876 0.244489 0.560043 0.061 Uiso 1 1 calc R . . . .
C00I C -0.0366(4) 0.6029(3) 0.3453(3) 0.0454(10) Uani 1 1 d . . . . .
H00I H -0.083353 0.653336 0.366847 0.055 Uiso 1 1 calc R . . . .
C00J C 0.1055(4) 0.4546(3) 0.2788(3) 0.0475(10) Uani 1 1 d . . . . .
H00J H 0.155242 0.406586 0.253909 0.057 Uiso 1 1 calc R . . . .
C00K C 0.5552(4) 0.6572(3) 0.8101(3) 0.0538(11) Uani 1 1 d . . . . .
H00K H 0.523746 0.704808 0.767362 0.065 Uiso 1 1 calc R . . . .
C00L C -0.0754(5) 0.5656(3) 0.2483(3) 0.0536(11) Uani 1 1 d . . . . .
H00L H -0.150875 0.588360 0.205215 0.064 Uiso 1 1 calc R . . . .
C00M C 0.4084(5) 0.1925(3) 0.4545(4) 0.0579(12) Uani 1 1 d . . . . .
H00M H 0.448504 0.136486 0.452087 0.070 Uiso 1 1 calc R . . . .
C00N C 0.5542(5) 0.5017(3) 0.8488(3) 0.0550(11) Uani 1 1 d . . . . .
H00N H 0.523424 0.444402 0.832969 0.066 Uiso 1 1 calc R . . . .
C00O C 0.2836(5) 0.2112(3) 0.3939(3) 0.0601(12) Uani 1 1 d . . . . .
H00O H 0.239042 0.166927 0.352023 0.072 Uiso 1 1 calc R . . . .
C00P C -0.0010(5) 0.4929(3) 0.2141(3) 0.0566(12) Uani 1 1 d . . . . .
H00P H -0.023811 0.469555 0.145742 0.068 Uiso 1 1 calc R . . . .
C00Q C 0.6496(5) 0.6715(4) 0.8969(4) 0.0731(15) Uani 1 1 d . . . . .
H00Q H 0.681664 0.728573 0.912592 0.088 Uiso 1 1 calc R . . . .
C00R C 0.6500(5) 0.5180(4) 0.9371(4) 0.0706(14) Uani 1 1 d . . . . .
H00R H 0.682413 0.471039 0.980626 0.085 Uiso 1 1 calc R . . . .
C00S C 0.6971(5) 0.6022(4) 0.9608(4) 0.0785(16) Uani 1 1 d . . . . .
H00S H 0.760918 0.612147 1.019875 0.094 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
Br01 C00D 1.878(4) . ?
O002 C00B 1.232(4) . ?
N003 C005 1.356(4) . ?
N003 C007 1.420(4) . ?
N003 C00A 1.415(4) . ?
N004 C006 1.299(4) . ?
N004 C008 1.396(5) . ?
C005 C006 1.439(5) . ?
C005 C009 1.373(5) . ?
C006 C00D 1.435(5) . ?
C007 C00C 1.410(5) . ?
C007 C00G 1.390(5) . ?
C008 C00A 1.409(5) . ?
C008 C00I 1.403(5) . ?
C009 C00B 1.424(5) . ?
C009 C00E 1.503(5) . ?
C00A C00J 1.397(5) . ?
C00B C00C 1.506(5) . ?
C00C C00H 1.394(5) . ?
C00D C00E 1.361(5) . ?
C00E C00F 1.466(5) . ?
C00F C00K 1.395(5) . ?
C00F C00N 1.390(6) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.365(5) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.375(6) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.357(5) . ?
C00J H00J 0.9300 . ?
C00J C00P 1.374(5) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.370(6) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.387(6) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.387(6) . ?
C00N H00N 0.9300 . ?
C00N C00R 1.397(6) . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00S 1.370(7) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.374(7) . ?
C00S H00S 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
C005 N003 C007 116.2(3) . . ?
C005 N003 C00A 116.3(3) . . ?
C00A N003 C007 127.5(3) . . ?
C006 N004 C008 114.2(3) . . ?
N003 C005 C006 120.6(3) . . ?
N003 C005 C009 128.1(3) . . ?
C009 C005 C006 111.3(3) . . ?
N004 C006 C005 124.7(3) . . ?
N004 C006 C00D 130.1(4) . . ?
C00D C006 C005 105.2(3) . . ?
C00C C007 N003 117.4(3) . . ?
C00G C007 N003 122.7(3) . . ?
C00G C007 C00C 119.8(3) . . ?
N004 C008 C00A 124.6(3) . . ?
N004 C008 C00I 116.7(4) . . ?
C00I C008 C00A 118.8(4) . . ?
C005 C009 C00B 119.2(3) . . ?
C005 C009 C00E 105.3(3) . . ?
C00B C009 C00E 135.3(3) . . ?
C008 C00A N003 118.0(3) . . ?
C00J C00A N003 122.8(3) . . ?
C00J C00A C008 119.2(3) . . ?
O002 C00B C009 127.2(4) . . ?
O002 C00B C00C 120.6(3) . . ?
C009 C00B C00C 112.1(3) . . ?
C007 C00C C00B 124.2(3) . . ?
C00H C00C C007 118.2(4) . . ?
C00H C00C C00B 117.4(3) . . ?
C006 C00D Br01 119.9(3) . . ?
C00E C00D Br01 129.6(3) . . ?
C00E C00D C006 110.3(3) . . ?
C00D C00E C009 107.9(3) . . ?
C00D C00E C00F 126.8(4) . . ?
C00F C00E C009 125.4(3) . . ?
C00K C00F C00E 119.7(4) . . ?
C00N C00F C00E 121.4(4) . . ?
C00N C00F C00K 118.8(4) . . ?
C007 C00G H00G 119.9 . . ?
C00O C00G C007 120.3(4) . . ?
C00O C00G H00G 119.9 . . ?
C00C C00H H00H 119.4 . . ?
C00M C00H C00C 121.2(4) . . ?
C00M C00H H00H 119.4 . . ?
C008 C00I H00I 119.3 . . ?
C00L C00I C008 121.3(4) . . ?
C00L C00I H00I 119.3 . . ?
C00A C00J H00J 120.3 . . ?
C00P C00J C00A 119.4(4) . . ?
C00P C00J H00J 120.3 . . ?
C00F C00K H00K 119.5 . . ?
C00Q C00K C00F 121.0(5) . . ?
C00Q C00K H00K 119.5 . . ?
C00I C00L H00L 120.4 . . ?
C00I C00L C00P 119.2(4) . . ?
C00P C00L H00L 120.4 . . ?
C00H C00M H00M 120.2 . . ?
C00H C00M C00O 119.6(4) . . ?
C00O C00M H00M 120.2 . . ?
C00F C00N H00N 120.4 . . ?
C00F C00N C00R 119.1(4) . . ?
C00R C00N H00N 120.4 . . ?
C00G C00O C00M 120.7(4) . . ?
C00G C00O H00O 119.7 . . ?
C00M C00O H00O 119.7 . . ?
C00J C00P C00L 121.6(4) . . ?
C00J C00P H00P 119.2 . . ?
C00L C00P H00P 119.2 . . ?
C00K C00Q H00Q 119.8 . . ?
C00K C00Q C00S 120.3(5) . . ?
C00S C00Q H00Q 119.8 . . ?
C00N C00R H00R 119.5 . . ?
C00S C00R C00N 121.0(5) . . ?
C00S C00R H00R 119.5 . . ?
C00Q C00S C00R 119.7(5) . . ?
C00Q C00S H00S 120.2 . . ?
C00R C00S H00S 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2047736'
loop_
_audit_author_name
_audit_author_address
'Sarasija Das'
;IISER Kolkata
India
;
_audit_update_record             
;
2020-12-02 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C24 H14 Br1.287 Cl0.713 N2'
_chemical_formula_weight         458.5
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yabc'
_symmetry_Int_Tables_number      14

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                   9.7636(3)
_cell_length_b                   9.7605(2)
_cell_length_c                   19.7943(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.084(2)
_cell_angle_gamma                90
_cell_volume                     1881.56(8)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5555(13) 1 0 0 0 1 0 0 0 1
2 0.4445(13) 1 0 -0.29 0 -1 0 0 0 -1

_cell_formula_units_Z            4

_cell_measurement_reflns_used    11659
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      66.08
_cell_measurement_temperature    100
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.6186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             917

_exptl_absorpt_coefficient_mu    4.709
_exptl_crystal_description       block
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            orange
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_T_max  1
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            5532
_diffrn_reflns_theta_min         4.92
_diffrn_reflns_theta_max         66.15
_diffrn_reflns_theta_full        66.15
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.99
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
The diffraction data is twinned by non-merohedry that has been reduced
into .hkl5 file containing reflections from both domains with a
transformation matrix. Outlier reflections were rejected that came 
from strongly overlapping peaks. Instability factor of 0.02 was employed
in order to obtain a converging refinement.
[Notes for Alert A and B in .checkcif report] 
;

_reflns_number_total             5506
_reflns_number_gt                5153
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_gt          0.0834
_refine_ls_R_factor_all          0.0569
_refine_ls_wR_factor_ref         0.0840
_refine_ls_goodness_of_fit_ref   3.33
_refine_ls_goodness_of_fit_gt    3.41
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         5506
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_number_constraints    66
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0004F²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0015
_refine_ls_shift/su_mean         0.0000
_refine_diff_density_max         1.34
_refine_diff_density_min         -1.02
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Br -0.6763 1.2805 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Cl 0.3639 0.7018 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.06442(5) 0.69389(4) 0.615687(19) Uani 0.02112(15) 4 1 d . . .
Cl1 Cl 0.45087(5) 0.32411(5) 0.40255(2) Uani 0.0250(3) 4 0.713(4) d . . .
N1 N 0.1673(3) 0.3792(3) 0.63654(15) Uani 0.0168(9) 4 1 d . . .
N2 N 0.3160(3) 0.2556(4) 0.53146(15) Uani 0.0170(9) 4 1 d . . .
C5 C 0.3189(4) 0.8133(4) 0.44719(19) Uani 0.0162(11) 4 1 d . . .
C6 C 0.2013(4) 0.7478(4) 0.46754(16) Uani 0.0154(11) 4 1 d . . .
C7 C 0.1990(4) 0.6083(4) 0.33088(18) Uani 0.0176(11) 4 1 d . . .
C8 C 0.2706(4) 0.3832(4) 0.52934(18) Uani 0.0157(11) 4 1 d . . .
C9 C 0.2170(4) 0.2470(4) 0.64191(17) Uani 0.0151(11) 4 1 d . . .
C10 C 0.2090(4) 0.6102(4) 0.49942(18) Uani 0.0164(11) 4 1 d . . .
C11 C 0.3091(4) 0.9402(4) 0.41611(19) Uani 0.0213(12) 4 1 d . . .
C12 C 0.0760(4) 0.8147(4) 0.45707(18) Uani 0.0161(11) 4 1 d . . .
C13 C 0.1590(4) 0.5789(4) 0.55898(18) Uani 0.0159(11) 4 1 d . . .
C14 C 0.4462(4) 0.6092(4) 0.32735(18) Uani 0.0185(11) 4 1 d . . .
C15 C 0.3285(4) 0.5641(4) 0.35691(17) Uani 0.0145(10) 4 1 d . . .
C16 C 0.0669(4) 0.9418(4) 0.42591(18) Uani 0.0182(11) 4 1 d . . .
C17 C 0.1831(4) 1.0038(4) 0.40495(19) Uani 0.0201(11) 4 1 d . . .
C18 C 0.1941(4) 0.4409(4) 0.58128(17) Uani 0.0140(10) 4 1 d . . .
C19 C 0.3410(4) 0.4728(4) 0.41586(18) Uani 0.0163(11) 4 1 d . . .
C20 C 0.2815(4) 0.4873(4) 0.47467(17) Uani 0.0148(10) 4 1 d . . .
C21 C 0.2876(4) 0.1836(4) 0.58945(19) Uani 0.0163(11) 4 1 d . . .
C22 C 0.3294(4) 0.0473(4) 0.59613(20) Uani 0.0195(11) 4 1 d . . .
C23 C 0.1899(4) 0.7009(4) 0.27756(18) Uani 0.0208(13) 4 1 d . . .
C24 C 0.4356(5) 0.7035(4) 0.2756(2) Uani 0.0228(13) 4 1 d . . .
C25 C 0.3075(4) 0.7499(5) 0.25030(18) Uani 0.0240(13) 4 1 d . . .
C26 C 0.3096(4) -0.0235(4) 0.6541(2) Uani 0.0247(13) 4 1 d . . .
C27 C 0.1983(4) 0.1701(4) 0.70122(19) Uani 0.0205(12) 4 1 d . . .
C28 C 0.2446(4) 0.0384(4) 0.70681(19) Uani 0.0222(12) 4 1 d . . .
Br2 Br 0.45087(5) 0.32411(5) 0.40255(2) Uani 0.0250(3) 4 0.287(4) d . . .
H1c5 H 0.406887 0.770045 0.454825 Uiso 0.0194 4 1 d . . .
H1c7 H 0.11739 0.574889 0.349674 Uiso 0.0211 4 1 d . . .
H1c11 H 0.390307 0.984272 0.402208 Uiso 0.0255 4 1 d . . .
H1c12 H -0.00556 0.772187 0.471646 Uiso 0.0193 4 1 d . . .
H1c14 H 0.534666 0.574195 0.343169 Uiso 0.0222 4 1 d . . .
H1c16 H -0.020464 0.986597 0.41894 Uiso 0.0219 4 1 d . . .
H1c17 H 0.176699 1.091139 0.382615 Uiso 0.0241 4 1 d . . .
H1c22 H 0.372164 0.003091 0.559775 Uiso 0.0234 4 1 d . . .
H1c23 H 0.101379 0.731419 0.259338 Uiso 0.025 4 1 d . . .
H1c24 H 0.517087 0.737448 0.256883 Uiso 0.0273 4 1 d . . .
H1c25 H 0.300359 0.815571 0.214115 Uiso 0.0288 4 1 d . . .
H1c26 H 0.340726 -0.116514 0.658714 Uiso 0.0296 4 1 d . . .
H1c27 H 0.152919 0.210919 0.737695 Uiso 0.0246 4 1 d . . .
H1c28 H 0.232219 -0.012407 0.747458 Uiso 0.0266 4 1 d . . .


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 N1 . . 3.249(3) ?
Br1 C13 . . 1.876(4) ?
Cl1 N2 . . 3.029(3) ?
Cl1 Br2 . . 0 ?
N1 C9 . . 1.380(5) ?
N1 C18 . . 1.291(5) ?
N2 C8 . . 1.322(5) ?
N2 C21 . . 1.390(5) ?
N2 Br2 . . 3.029(3) ?
C5 C6 . . 1.398(6) ?
C5 C11 . . 1.382(6) ?
C5 H1c5 . . 0.96 ?
C6 C10 . . 1.483(5) ?
C6 C12 . . 1.390(6) ?
C7 C15 . . 1.399(5) ?
C7 C23 . . 1.388(5) ?
C7 H1c7 . . 0.96 ?
C8 C18 . . 1.429(5) ?
C8 C20 . . 1.494(5) ?
C9 C21 . . 1.428(5) ?
C9 C27 . . 1.416(5) ?
C10 C13 . . 1.343(5) ?
C10 C20 . . 1.494(5) ?
C11 C17 . . 1.381(6) ?
C11 H1c11 . . 0.96 ?
C12 C16 . . 1.386(5) ?
C12 H1c12 . . 0.96 ?
C13 C18 . . 1.451(5) ?
C14 C15 . . 1.397(6) ?
C14 C24 . . 1.376(6) ?
C14 H1c14 . . 0.96 ?
C15 C19 . . 1.466(5) ?
C16 C17 . . 1.376(6) ?
C16 H1c16 . . 0.96 ?
C17 H1c17 . . 0.96 ?
C19 C20 . . 1.345(5) ?
C19 Br2 . . 1.835(4) ?
C21 C22 . . 1.394(5) ?
C22 C26 . . 1.365(6) ?
C22 H1c22 . . 0.96 ?
C23 C25 . . 1.388(6) ?
C23 H1c23 . . 0.96 ?
C24 C25 . . 1.390(6) ?
C24 H1c24 . . 0.96 ?
C25 H1c25 . . 0.96 ?
C26 C28 . . 1.396(6) ?
C26 H1c26 . . 0.96 ?
C27 C28 . . 1.365(6) ?
C27 H1c27 . . 0.96 ?
C28 H1c28 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Br1 C13 . . . 49.41(12) ?
N2 Cl1 Br2 . . . 0 ?
Br1 N1 C9 . . . 176.1(2) ?
Br1 N1 C18 . . . 62.1(2) ?
C9 N1 C18 . . . 114.2(3) ?
Cl1 N2 C8 . . . 86.0(2) ?
Cl1 N2 C21 . . . 158.6(3) ?
Cl1 N2 Br2 . . . 0 ?
C8 N2 C21 . . . 114.6(3) ?
C8 N2 Br2 . . . 86.0(2) ?
C21 N2 Br2 . . . 158.6(3) ?
C6 C5 C11 . . . 120.4(4) ?
C6 C5 H1c5 . . . 119.81 ?
C11 C5 H1c5 . . . 119.81 ?
C5 C6 C10 . . . 121.3(3) ?
C5 C6 C12 . . . 118.3(3) ?
C10 C6 C12 . . . 120.4(3) ?
C15 C7 C23 . . . 119.2(4) ?
C15 C7 H1c7 . . . 120.41 ?
C23 C7 H1c7 . . . 120.4 ?
N2 C8 C18 . . . 122.7(3) ?
N2 C8 C20 . . . 128.5(3) ?
C18 C8 C20 . . . 108.7(3) ?
N1 C9 C21 . . . 122.3(3) ?
N1 C9 C27 . . . 119.6(3) ?
C21 C9 C27 . . . 118.1(3) ?
C6 C10 C13 . . . 124.7(3) ?
C6 C10 C20 . . . 126.8(3) ?
C13 C10 C20 . . . 108.4(3) ?
C5 C11 C17 . . . 120.4(4) ?
C5 C11 H1c11 . . . 119.78 ?
C17 C11 H1c11 . . . 119.78 ?
C6 C12 C16 . . . 121.0(4) ?
C6 C12 H1c12 . . . 119.51 ?
C16 C12 H1c12 . . . 119.51 ?
Br1 C13 C10 . . . 127.9(3) ?
Br1 C13 C18 . . . 119.3(3) ?
C10 C13 C18 . . . 112.7(3) ?
C15 C14 C24 . . . 120.1(4) ?
C15 C14 H1c14 . . . 119.94 ?
C24 C14 H1c14 . . . 119.94 ?
C7 C15 C14 . . . 119.8(3) ?
C7 C15 C19 . . . 120.1(3) ?
C14 C15 C19 . . . 120.0(3) ?
C12 C16 C17 . . . 120.0(4) ?
C12 C16 H1c16 . . . 119.98 ?
C17 C16 H1c16 . . . 119.98 ?
C11 C17 C16 . . . 119.8(4) ?
C11 C17 H1c17 . . . 120.09 ?
C16 C17 H1c17 . . . 120.09 ?
N1 C18 C8 . . . 125.0(4) ?
N1 C18 C13 . . . 129.2(3) ?
C8 C18 C13 . . . 105.7(3) ?
C15 C19 C20 . . . 127.5(3) ?
C15 C19 Br2 . . . 112.5(3) ?
C20 C19 Br2 . . . 120.0(3) ?
C8 C20 C10 . . . 104.4(3) ?
C8 C20 C19 . . . 127.8(3) ?
C10 C20 C19 . . . 127.7(3) ?
N2 C21 C9 . . . 121.1(3) ?
N2 C21 C22 . . . 119.1(3) ?
C9 C21 C22 . . . 119.8(3) ?
C21 C22 C26 . . . 120.3(4) ?
C21 C22 H1c22 . . . 119.85 ?
C26 C22 H1c22 . . . 119.85 ?
C7 C23 C25 . . . 120.7(4) ?
C7 C23 H1c23 . . . 119.65 ?
C25 C23 H1c23 . . . 119.65 ?
C14 C24 C25 . . . 120.3(4) ?
C14 C24 H1c24 . . . 119.85 ?
C25 C24 H1c24 . . . 119.85 ?
C23 C25 C24 . . . 119.7(4) ?
C23 C25 H1c25 . . . 120.13 ?
C24 C25 H1c25 . . . 120.13 ?
C22 C26 C28 . . . 120.6(4) ?
C22 C26 H1c26 . . . 119.72 ?
C28 C26 H1c26 . . . 119.73 ?
C9 C27 C28 . . . 120.3(4) ?
C9 C27 H1c27 . . . 119.83 ?
C28 C27 H1c27 . . . 119.83 ?
C26 C28 C27 . . . 120.8(4) ?
C26 C28 H1c28 . . . 119.59 ?
C27 C28 H1c28 . . . 119.59 ?
Cl1 Br2 N2 . . . 0 ?
Cl1 Br2 C19 . . . 0 ?
N2 Br2 C19 . . . 76.11(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H1c5 N2 . . 3_666 0.96 2.71 3.623(5) 158.76 ?
C7 H1c7 N1 . . 3_566 0.96 2.85 3.681(5) 145.73 ?
C11 H1c11 C22 . . 3_666 0.96 2.75 3.558(6) 141.97 ?
C12 H1c12 C8 . . 3_566 0.96 3.00 3.922(5) 161.86 ?
C12 H1c12 C18 . . 3_566 0.96 2.92 3.669(5) 135.60 ?
C12 H1c12 C21 . . 3_566 0.96 2.96 3.603(5) 125.56 ?
C14 H1c14 N1 . . 3_666 0.96 2.94 3.792(5) 147.87 ?
C14 H1c14 C9 . . 3_666 0.96 2.99 3.588(5) 122.00 ?
C14 H1c14 C18 . . 3_666 0.96 2.95 3.865(5) 159.55 ?
C22 H1c22 C5 . . 1_545 0.96 2.92 3.725(5) 142.65 ?
C22 H1c22 C11 . . 1_545 0.96 2.93 3.705(5) 138.47 ?
C24 H1c24 Br1 . . 4_564 0.96 2.94 3.629(4) 129.47 ?
C24 H1c24 C27 . . 3_666 0.96 2.98 3.778(6) 141.10 ?
C25 H1c25 C7 . . 2_555 0.96 2.99 3.848(6) 149.08 ?
C28 H1c28 N1 . . 2_546 0.96 2.65 3.520(5) 150.56 ?


# start Validation Reply Form
_vrf_PLAT992_I                   
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by 1392 Check
RESPONSE: The refinement is done using JANA2006 based on the
criterion of observability I > 3sigma(I) which reduces the number
of observed reflections as compared to shelx, and thus such large difference.
In addition, this dataset is twinned and outliers were rejected 
specially pertaining to severely overlapping peaks from non-merohedral
domains at certain geometry of the diffractometer.
;
# end Validation Reply Form
