# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2045826'
loop_
_audit_author_name
_audit_author_address
'snoxma smoile'
;CSIR CLRI
India
;
_audit_update_record             
;
2020-11-23 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1-allyl-3-bromo-2-phenyl-1H-indole
_chemical_name_common            SS1-246RF1
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 Br N'
_chemical_formula_sum            'C17 H14 Br N'
_chemical_formula_weight         312.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.2567(5)
_cell_length_b                   19.7843(11)
_cell_length_c                   8.8668(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1448.42(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9099
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      28.29
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.823
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4940
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40196
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.851
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3972
_reflns_number_gt                3045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.978

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.4683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3972
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0653(6) 0.81146(18) -0.0004(5) 0.0548(9) Uani 1 1 d . . . . .
H1 H 0.025554 0.802744 -0.096604 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0251(6) 0.7695(2) 0.1178(6) 0.0682(13) Uani 1 1 d . . . . .
H2 H -0.042366 0.732638 0.100576 0.082 Uiso 1 1 calc R U . . .
C3 C 0.0822(7) 0.7809(2) 0.2589(6) 0.0686(13) Uani 1 1 d . . . . .
H3 H 0.054791 0.751872 0.337298 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1810(6) 0.8358(3) 0.2859(5) 0.0635(11) Uani 1 1 d . . . . .
H4 H 0.219549 0.843934 0.382730 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2228(5) 0.87862(19) 0.1696(4) 0.0492(9) Uani 1 1 d . . . . .
H5 H 0.289675 0.915505 0.188250 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1655(4) 0.86694(16) 0.0245(4) 0.0410(7) Uani 1 1 d . . . . .
C7 C 0.2115(4) 0.91086(15) -0.1024(4) 0.0381(7) Uani 1 1 d . . . . .
C8 C 0.2907(4) 0.89571(16) -0.2330(4) 0.0410(7) Uani 1 1 d . . . . .
C9 C 0.3151(4) 0.95523(17) -0.3185(4) 0.0390(7) Uani 1 1 d . . . . .
C10 C 0.3867(4) 0.9703(2) -0.4576(4) 0.0495(9) Uani 1 1 d . . . . .
H10 H 0.434426 0.936525 -0.515411 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3846(5) 1.0365(2) -0.5069(5) 0.0581(10) Uani 1 1 d . . . . .
H11 H 0.432309 1.047199 -0.598832 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3128(5) 1.0875(2) -0.4219(5) 0.0573(10) Uani 1 1 d . . . . .
H12 H 0.312113 1.131436 -0.459098 0.069 Uiso 1 1 calc R U . . .
C13 C 0.2423(4) 1.07429(16) -0.2835(6) 0.0482(7) Uani 1 1 d . . . . .
H13 H 0.195496 1.108560 -0.226530 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2443(4) 1.00765(16) -0.2329(4) 0.0383(7) Uani 1 1 d . . . . .
C15 C 0.0794(4) 1.01722(19) 0.0035(5) 0.0487(8) Uani 1 1 d . . . . .
H15A H 0.018923 0.985024 0.063812 0.058 Uiso 1 1 calc R U . . .
H15B H 0.002133 1.044139 -0.052943 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1740(6) 1.0625(3) 0.1059(6) 0.0701(13) Uani 1 1 d . . . . .
H16 H 0.263017 1.043455 0.154066 0.084 Uiso 1 1 calc R U . . .
C17 C 0.1458(8) 1.1234(3) 0.1336(9) 0.101(2) Uani 1 1 d . . . . .
H17A H 0.058232 1.144875 0.088318 0.122 Uiso 1 1 calc R U . . .
H17B H 0.212518 1.147176 0.199383 0.122 Uiso 1 1 calc R U . . .
N1 N 0.1830(3) 0.98050(13) -0.1020(3) 0.0379(6) Uani 1 1 d . . . . .
Br1 Br 0.36674(7) 0.81009(2) -0.28992(8) 0.0769(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(6) . ?
C1 C6 1.392(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.472(5) . ?
C7 C8 1.363(5) . ?
C7 N1 1.398(4) . ?
C8 C9 1.415(5) . ?
C8 Br1 1.876(3) . ?
C9 C10 1.399(5) . ?
C9 C14 1.412(5) . ?
C10 C11 1.380(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(4) . ?
C13 H13 0.9300 . ?
C14 N1 1.375(4) . ?
C15 N1 1.461(4) . ?
C15 C16 1.496(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.250(7) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 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
C2 C1 C6 119.8(4) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 119.9(3) . . ?
C8 C7 N1 107.5(3) . . ?
C8 C7 C6 130.1(3) . . ?
N1 C7 C6 122.4(3) . . ?
C7 C8 C9 109.9(3) . . ?
C7 C8 Br1 126.0(3) . . ?
C9 C8 Br1 124.0(2) . . ?
C10 C9 C14 119.5(3) . . ?
C10 C9 C8 135.2(3) . . ?
C14 C9 C8 105.3(3) . . ?
C11 C10 C9 118.4(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 117.4(4) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
N1 C14 C13 129.6(3) . . ?
N1 C14 C9 108.6(3) . . ?
C13 C14 C9 121.8(3) . . ?
N1 C15 C16 112.4(3) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 126.8(5) . . ?
C17 C16 H16 116.6 . . ?
C15 C16 H16 116.6 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C14 N1 C7 108.7(3) . . ?
C14 N1 C15 124.2(3) . . ?
C7 N1 C15 126.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C4 C5 C6 C7 -178.4(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C1 C6 C7 178.5(4) . . . . ?
C5 C6 C7 C8 119.7(4) . . . . ?
C1 C6 C7 C8 -58.8(5) . . . . ?
C5 C6 C7 N1 -57.4(5) . . . . ?
C1 C6 C7 N1 124.1(4) . . . . ?
N1 C7 C8 C9 0.3(4) . . . . ?
C6 C7 C8 C9 -177.2(3) . . . . ?
N1 C7 C8 Br1 177.4(2) . . . . ?
C6 C7 C8 Br1 0.0(5) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
Br1 C8 C9 C10 3.0(5) . . . . ?
C7 C8 C9 C14 -0.7(4) . . . . ?
Br1 C8 C9 C14 -177.9(2) . . . . ?
C14 C9 C10 C11 -0.3(5) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C14 -0.7(6) . . . . ?
C12 C13 C14 N1 -179.5(3) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C10 C9 C14 N1 -179.9(3) . . . . ?
C8 C9 C14 N1 0.8(3) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
C8 C9 C14 C13 -178.8(3) . . . . ?
N1 C15 C16 C17 130.9(6) . . . . ?
C13 C14 N1 C7 178.9(3) . . . . ?
C9 C14 N1 C7 -0.7(3) . . . . ?
C13 C14 N1 C15 9.4(5) . . . . ?
C9 C14 N1 C15 -170.2(3) . . . . ?
C8 C7 N1 C14 0.3(4) . . . . ?
C6 C7 N1 C14 177.9(3) . . . . ?
C8 C7 N1 C15 169.5(3) . . . . ?
C6 C7 N1 C15 -12.8(5) . . . . ?
C16 C15 N1 C14 -80.4(5) . . . . ?
C16 C15 N1 C7 112.0(4) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2101632'
loop_
_audit_author_name
_audit_author_address
'Suresh Snoxma smile'
;CSIR CLRI
India
;
_audit_update_record             
;
2021-08-05 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
N-allyl-5-bromo-N-phenyl-2-(p-tolylamino)benzamide
_chemical_name_common            SS1-280R
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Br N2 O'
_chemical_formula_sum            'C23 H21 Br N2 O'
_chemical_formula_weight         421.33

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.519(3)
_cell_length_b                   9.117(2)
_cell_length_c                   20.975(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.312(7)
_cell_angle_gamma                90
_cell_volume                     2011.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3029
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      22.02
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.058
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4182
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15037
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.942
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3742
_reflns_number_gt                2016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3742
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2030(5) 0.3703(5) 0.3002(2) 0.0586(14) Uani 1 1 d . . . . .
H1 H 0.274289 0.311203 0.294915 0.070 Uiso 1 1 calc R U . . .
C2 C 0.1531(7) 0.4485(8) 0.2488(3) 0.088(2) Uani 1 1 d . . . . .
H2 H 0.191269 0.441774 0.208986 0.106 Uiso 1 1 calc R U . . .
C3 C 0.0492(7) 0.5345(8) 0.2565(4) 0.098(3) Uani 1 1 d . . . . .
H3 H 0.017009 0.587505 0.222175 0.117 Uiso 1 1 calc R U . . .
C4 C -0.0081(6) 0.5436(6) 0.3141(4) 0.085(2) Uani 1 1 d . . . . .
H4 H -0.080425 0.601195 0.318821 0.101 Uiso 1 1 calc R U . . .
C5 C 0.0403(5) 0.4677(5) 0.3658(3) 0.0623(15) Uani 1 1 d . . . . .
H5 H 0.001375 0.475188 0.405337 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1461(4) 0.3812(4) 0.3586(2) 0.0400(11) Uani 1 1 d . . . . .
C7 C 0.3135(4) 0.2838(5) 0.4313(2) 0.0353(11) Uani 1 1 d . . . . .
C8 C 0.4031(4) 0.4058(4) 0.41535(18) 0.0340(11) Uani 1 1 d . . . . .
C9 C 0.3638(4) 0.5509(4) 0.42389(18) 0.0390(12) Uani 1 1 d . . . . .
H9 H 0.279823 0.570547 0.434579 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4485(5) 0.6655(4) 0.41660(19) 0.0379(12) Uani 1 1 d . . . . .
C11 C 0.5728(5) 0.6374(5) 0.4016(2) 0.0478(12) Uani 1 1 d . . . . .
H11 H 0.629662 0.714681 0.396889 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6140(4) 0.4940(5) 0.3934(2) 0.0450(12) Uani 1 1 d . . . . .
H12 H 0.698291 0.475455 0.382861 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5294(4) 0.3782(4) 0.40081(19) 0.0376(11) Uani 1 1 d . . . . .
C14 C 0.6771(4) 0.1793(4) 0.3637(2) 0.0376(11) Uani 1 1 d . . . . .
C15 C 0.7288(4) 0.0455(5) 0.3845(2) 0.0461(12) Uani 1 1 d . . . . .
H15 H 0.692931 -0.003884 0.418747 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8326(5) -0.0119(5) 0.3540(2) 0.0529(13) Uani 1 1 d . . . . .
H16 H 0.864183 -0.101781 0.367841 0.064 Uiso 1 1 calc R U . . .
C17 C 0.8921(5) 0.0568(6) 0.3040(2) 0.0515(13) Uani 1 1 d . . . . .
C18 C 0.8397(5) 0.1862(5) 0.2832(2) 0.0516(14) Uani 1 1 d . . . . .
H18 H 0.876445 0.235006 0.249034 0.062 Uiso 1 1 calc R U . . .
C19 C 0.7352(5) 0.2449(5) 0.3115(2) 0.0480(13) Uani 1 1 d . . . . .
H19 H 0.701423 0.331734 0.295369 0.058 Uiso 1 1 calc R U . . .
C20 C 1.0124(5) -0.0039(6) 0.2749(2) 0.0744(17) Uani 1 1 d . . . . .
H20A H 1.029963 0.046853 0.235808 0.112 Uiso 1 1 calc R U . . .
H20B H 1.001492 -0.106602 0.266274 0.112 Uiso 1 1 calc R U . . .
H20C H 1.082115 0.009377 0.304044 0.112 Uiso 1 1 calc R U . . .
C21 C 0.1015(5) 0.1836(5) 0.4365(2) 0.0529(14) Uani 1 1 d . . . . .
H21A H 0.143341 0.089015 0.439233 0.063 Uiso 1 1 calc R U . . .
H21B H 0.029832 0.173933 0.407530 0.063 Uiso 1 1 calc R U . . .
C22 C 0.0543(5) 0.2249(6) 0.5004(3) 0.0689(16) Uani 1 1 d . . . . .
H22 H 0.115016 0.255074 0.530009 0.083 Uiso 1 1 calc R U . . .
C23 C -0.0588(6) 0.2235(6) 0.5187(3) 0.094(2) Uani 1 1 d . . . . .
H23A H -0.123125 0.194216 0.490905 0.113 Uiso 1 1 calc R U . . .
H23B H -0.078436 0.251709 0.560099 0.113 Uiso 1 1 calc R U . . .
N2 N 0.1915(3) 0.2924(4) 0.41053(16) 0.0388(9) Uani 1 1 d . . . . .
O1 O 0.3497(3) 0.1826(3) 0.46466(15) 0.0525(9) Uani 1 1 d . . . . .
Br1 Br 0.39402(5) 0.86114(5) 0.42991(2) 0.0530(2) Uani 1 1 d . . . . .
N1 N 0.5687(4) 0.2319(4) 0.39337(19) 0.0463(11) Uani 1 1 d . . . . .
H1A H 0.531(4) 0.176(4) 0.4199(19) 0.056 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.371(6) . ?
C1 C2 1.393(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C6 N2 1.436(5) . ?
C7 O1 1.218(4) . ?
C7 N2 1.355(5) . ?
C7 C8 1.498(6) . ?
C8 C13 1.388(5) . ?
C8 C9 1.397(5) . ?
C9 C10 1.382(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 Br1 1.895(4) . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 N1 1.405(5) . ?
C14 N1 1.388(5) . ?
C14 C19 1.392(6) . ?
C14 C15 1.404(6) . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(6) . ?
C17 C20 1.513(6) . ?
C18 C19 1.361(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.478(5) . ?
C21 C22 1.480(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.252(7) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
N1 H1A 0.85(4) . ?

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
C6 C1 C2 119.4(5) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 119.8(5) . . ?
C1 C6 N2 119.4(4) . . ?
C5 C6 N2 120.5(4) . . ?
O1 C7 N2 121.4(4) . . ?
O1 C7 C8 119.8(4) . . ?
N2 C7 C8 118.7(4) . . ?
C13 C8 C9 119.0(4) . . ?
C13 C8 C7 121.2(4) . . ?
C9 C8 C7 119.2(4) . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 Br1 120.0(3) . . ?
C9 C10 Br1 120.0(4) . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.0(4) . . ?
C8 C13 N1 118.7(4) . . ?
C12 C13 N1 121.3(4) . . ?
N1 C14 C19 124.7(4) . . ?
N1 C14 C15 118.6(4) . . ?
C19 C14 C15 116.6(4) . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 123.2(5) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C18 C17 C16 116.7(4) . . ?
C18 C17 C20 121.5(5) . . ?
C16 C17 C20 121.8(5) . . ?
C19 C18 C17 121.6(5) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 122.1(4) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 112.5(4) . . ?
N2 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N2 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 126.8(6) . . ?
C23 C22 H22 116.6 . . ?
C21 C22 H22 116.6 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C7 N2 C6 126.0(4) . . ?
C7 N2 C21 116.7(4) . . ?
C6 N2 C21 116.5(4) . . ?
C14 N1 C13 128.4(4) . . ?
C14 N1 H1A 118(3) . . ?
C13 N1 H1A 111(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(9) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C2 C3 C4 C5 1.3(10) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C6 N2 175.4(4) . . . . ?
C4 C5 C6 C1 -0.1(7) . . . . ?
C4 C5 C6 N2 -175.0(4) . . . . ?
O1 C7 C8 C13 40.3(6) . . . . ?
N2 C7 C8 C13 -142.7(4) . . . . ?
O1 C7 C8 C9 -130.6(4) . . . . ?
N2 C7 C8 C9 46.4(6) . . . . ?
C13 C8 C9 C10 1.4(6) . . . . ?
C7 C8 C9 C10 172.6(4) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C8 C9 C10 Br1 -178.9(3) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
Br1 C10 C11 C12 178.4(3) . . . . ?
C10 C11 C12 C13 -0.5(7) . . . . ?
C9 C8 C13 C12 -1.6(6) . . . . ?
C7 C8 C13 C12 -172.6(4) . . . . ?
C9 C8 C13 N1 178.9(4) . . . . ?
C7 C8 C13 N1 8.0(6) . . . . ?
C11 C12 C13 C8 1.2(7) . . . . ?
C11 C12 C13 N1 -179.4(4) . . . . ?
N1 C14 C15 C16 177.1(4) . . . . ?
C19 C14 C15 C16 1.0(6) . . . . ?
C14 C15 C16 C17 1.5(7) . . . . ?
C15 C16 C17 C18 -2.6(7) . . . . ?
C15 C16 C17 C20 175.2(4) . . . . ?
C16 C17 C18 C19 1.1(7) . . . . ?
C20 C17 C18 C19 -176.6(4) . . . . ?
C17 C18 C19 C14 1.4(7) . . . . ?
N1 C14 C19 C18 -178.3(4) . . . . ?
C15 C14 C19 C18 -2.5(6) . . . . ?
N2 C21 C22 C23 132.8(6) . . . . ?
O1 C7 N2 C6 -162.3(4) . . . . ?
C8 C7 N2 C6 20.8(6) . . . . ?
O1 C7 N2 C21 7.2(6) . . . . ?
C8 C7 N2 C21 -169.7(3) . . . . ?
C1 C6 N2 C7 53.1(6) . . . . ?
C5 C6 N2 C7 -132.0(5) . . . . ?
C1 C6 N2 C21 -116.3(5) . . . . ?
C5 C6 N2 C21 58.5(5) . . . . ?
C22 C21 N2 C7 81.2(5) . . . . ?
C22 C21 N2 C6 -108.4(5) . . . . ?
C19 C14 N1 C13 -32.5(7) . . . . ?
C15 C14 N1 C13 151.8(4) . . . . ?
C8 C13 N1 C14 161.8(4) . . . . ?
C12 C13 N1 C14 -17.6(7) . . . . ?

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
N1 H1A O1 0.85(4) 2.13(4) 2.790(5) 134(4) . yes

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.077


# start Validation Reply Form
_vrf_PLAT431_shelx               
;
PROBLEM: Short Inter HL..A Contact  Br1      ..O1       .       3.06 Ang.  
RESPONSE: This intermoleculat contact is between C=O...Br and this is
not due to missed hydrogen bond
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
