# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_BM-DE-34_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1903384'
loop_
_audit_author_name
_audit_author_address
'Chandan Gharui'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 Br N O2'
_chemical_formula_sum            'C23 H20 Br N O2'
_chemical_formula_weight         422.30

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   13.351(4)
_cell_length_b                   25.715(7)
_cell_length_c                   5.7490(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1973.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2442
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      13.25

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70247
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_av_R_equivalents  0.2937
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.584
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_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             3497
_reflns_number_gt                1942
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3497
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1851
_refine_ls_R_factor_gt           0.1147
_refine_ls_wR_factor_ref         0.2477
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   1.880
_refine_ls_restrained_S_all      1.880
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001

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
Br1 Br 0.37337(18) 0.46310(9) 1.0785(5) 0.0895(9) Uani 1 1 d . . . . .
O1 O 0.0216(9) 0.3583(4) 0.409(2) 0.059(3) Uani 1 1 d . . . . .
O2 O -0.1739(18) 0.4412(9) 0.485(6) 0.202(14) Uani 1 1 d . . . . .
N1 N 0.3143(15) 0.2527(8) 0.277(3) 0.079(6) Uani 1 1 d . . . . .
C1 C 0.0634(17) 0.1997(9) 0.230(4) 0.083(7) Uani 1 1 d . . . . .
C2 C 0.032(2) 0.1801(9) 0.445(5) 0.125(11) Uani 1 1 d . . . . .
H2 H 0.0108 0.2035 0.5583 0.150 Uiso 1 1 calc R U . . .
C3 C 0.0316(19) 0.1264(10) 0.499(4) 0.093(8) Uani 1 1 d . . . . .
H3 H 0.0066 0.1123 0.6364 0.111 Uiso 1 1 calc R U . . .
C4 C 0.0756(17) 0.0957(11) 0.309(10) 0.17(2) Uani 1 1 d . . . . .
H4 H 0.0825 0.0601 0.3301 0.208 Uiso 1 1 calc R U . . .
C5 C 0.104(2) 0.1151(13) 0.119(4) 0.091(8) Uani 1 1 d . . . . .
H5 H 0.1298 0.0922 0.0090 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1018(16) 0.1676(10) 0.059(5) 0.091(7) Uani 1 1 d . . . . .
H6 H 0.1240 0.1799 -0.0843 0.109 Uiso 1 1 calc R U . . .
C7 C -0.0486(16) 0.2806(7) 0.228(4) 0.064(6) Uani 1 1 d . . . . .
H7A H -0.0947 0.2695 0.1075 0.077 Uiso 1 1 calc R U . . .
H7B H -0.0727 0.2668 0.3746 0.077 Uiso 1 1 calc R U . . .
C8 C 0.0520(13) 0.2577(7) 0.179(3) 0.051(5) Uani 1 1 d . . . . .
H8 H 0.0645 0.2623 0.0120 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1295(18) 0.2878(8) 0.303(3) 0.069(5) Uani 1 1 d . . . . .
C10 C 0.241(2) 0.2699(8) 0.289(4) 0.071(7) Uani 1 1 d . . . . .
C11 C 0.1098(15) 0.3341(7) 0.435(4) 0.063(5) Uani 1 1 d . . . . .
C12 C 0.1811(13) 0.3633(7) 0.557(3) 0.051(5) Uani 1 1 d . . . . .
C13 C 0.1824(14) 0.4181(8) 0.547(4) 0.067(5) Uani 1 1 d . . . . .
H13 H 0.1420 0.4353 0.4402 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2451(17) 0.4477(8) 0.701(4) 0.075(6) Uani 1 1 d . . . . .
H14 H 0.2481 0.4837 0.6869 0.089 Uiso 1 1 calc R U . . .
C15 C 0.2978(13) 0.4239(8) 0.859(3) 0.061(6) Uani 1 1 d . . . . .
C16 C 0.3034(15) 0.3679(8) 0.891(4) 0.077(6) Uani 1 1 d . . . . .
H16 H 0.3406 0.3516 1.0072 0.093 Uiso 1 1 calc R U . . .
C17 C 0.2441(14) 0.3409(7) 0.721(4) 0.064(6) Uani 1 1 d . . . . .
H17 H 0.2482 0.3048 0.7215 0.077 Uiso 1 1 calc R U . . .
C18 C -0.0503(15) 0.3378(10) 0.240(4) 0.085(8) Uani 1 1 d . . . . .
C19 C -0.0237(16) 0.3638(11) -0.005(3) 0.090(8) Uani 1 1 d . . . . .
H19A H 0.0419 0.3518 -0.0535 0.108 Uiso 1 1 calc R U . . .
H19B H -0.0718 0.3520 -0.1196 0.108 Uiso 1 1 calc R U . . .
C20 C -0.0234(18) 0.4255(9) -0.004(4) 0.084(7) Uani 1 1 d . . . . .
H20A H -0.0165 0.4389 -0.1605 0.100 Uiso 1 1 calc R U . . .
H20B H 0.0314 0.4386 0.0903 0.100 Uiso 1 1 calc R U . . .
C21 C -0.128(2) 0.4422(9) 0.105(6) 0.121(9) Uani 1 1 d . . . . .
H21A H -0.1267 0.4792 0.1382 0.145 Uiso 1 1 calc R U . . .
H21B H -0.1804 0.4364 -0.0103 0.145 Uiso 1 1 calc R U . . .
C22 C -0.1538(17) 0.4163(10) 0.303(5) 0.083(7) Uani 1 1 d . . . . .
C23 C -0.1530(13) 0.3602(8) 0.317(3) 0.066(6) Uani 1 1 d . . . . .
H23A H -0.2052 0.3463 0.2170 0.079 Uiso 1 1 calc R U . . .
H23B H -0.1671 0.3495 0.4749 0.079 Uiso 1 1 calc R 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
Br1 C15 1.904(17) . ?
O1 C11 1.339(19) . ?
O1 C18 1.46(2) . ?
O2 C22 1.25(3) . ?
N1 C10 1.07(3) . ?
C1 C6 1.38(3) . ?
C1 C2 1.40(3) . ?
C1 C8 1.53(3) . ?
C2 C3 1.42(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.47(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.26(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C18 1.47(3) . ?
C7 C8 1.49(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.48(3) . ?
C8 H8 0.9800 . ?
C9 C11 1.43(3) . ?
C9 C10 1.56(3) . ?
C11 C12 1.40(2) . ?
C12 C17 1.39(2) . ?
C12 C13 1.41(2) . ?
C13 C14 1.43(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.30(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.45(3) . ?
C16 C17 1.44(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.55(2) . ?
C18 C19 1.60(3) . ?
C19 C20 1.58(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.59(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.36(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.45(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C11 O1 C18 118.9(15) . . ?
C6 C1 C2 122(2) . . ?
C6 C1 C8 119(2) . . ?
C2 C1 C8 120(2) . . ?
C1 C2 C3 123(2) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C2 C3 C4 111(2) . . ?
C2 C3 H3 124.5 . . ?
C4 C3 H3 124.5 . . ?
C5 C4 C3 124(3) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C6 126(3) . . ?
C4 C5 H5 116.9 . . ?
C6 C5 H5 116.8 . . ?
C1 C6 C5 114(2) . . ?
C1 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
C18 C7 C8 114.6(17) . . ?
C18 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C18 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 109.3(16) . . ?
C9 C8 C1 110.3(16) . . ?
C7 C8 C1 116.0(17) . . ?
C9 C8 H8 106.9 . . ?
C7 C8 H8 106.9 . . ?
C1 C8 H8 106.9 . . ?
C11 C9 C8 124.2(19) . . ?
C11 C9 C10 116.6(19) . . ?
C8 C9 C10 119.2(17) . . ?
N1 C10 C9 173(2) . . ?
O1 C11 C12 113.9(17) . . ?
O1 C11 C9 119.2(18) . . ?
C12 C11 C9 125.7(18) . . ?
C17 C12 C11 122.0(18) . . ?
C17 C12 C13 115.7(17) . . ?
C11 C12 C13 121.5(19) . . ?
C12 C13 C14 120.9(18) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.7(19) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 125.6(18) . . ?
C14 C15 Br1 120.0(17) . . ?
C16 C15 Br1 114.3(16) . . ?
C17 C16 C15 111.3(18) . . ?
C17 C16 H16 124.3 . . ?
C15 C16 H16 124.3 . . ?
C12 C17 C16 126.6(17) . . ?
C12 C17 H17 116.7 . . ?
C16 C17 H17 116.7 . . ?
O1 C18 C7 112(2) . . ?
O1 C18 C23 105.0(15) . . ?
C7 C18 C23 113.4(18) . . ?
O1 C18 C19 106.8(16) . . ?
C7 C18 C19 111.8(19) . . ?
C23 C18 C19 107(2) . . ?
C20 C19 C18 114.5(18) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 105.6(19) . . ?
C19 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
C19 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.7 . . ?
C22 C21 C20 114(2) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
O2 C22 C21 120(3) . . ?
O2 C22 C23 118(3) . . ?
C21 C22 C23 122(2) . . ?
C22 C23 C18 111.3(19) . . ?
C22 C23 H23A 109.4 . . ?
C18 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C18 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?

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 -4(4) . . . . ?
C8 C1 C2 C3 174(2) . . . . ?
C1 C2 C3 C4 5(4) . . . . ?
C2 C3 C4 C5 -4(5) . . . . ?
C3 C4 C5 C6 1(6) . . . . ?
C2 C1 C6 C5 1(3) . . . . ?
C8 C1 C6 C5 -176.9(19) . . . . ?
C4 C5 C6 C1 0(4) . . . . ?
C18 C7 C8 C9 38(2) . . . . ?
C18 C7 C8 C1 164(2) . . . . ?
C6 C1 C8 C9 -106(2) . . . . ?
C2 C1 C8 C9 76(3) . . . . ?
C6 C1 C8 C7 129(2) . . . . ?
C2 C1 C8 C7 -49(3) . . . . ?
C7 C8 C9 C11 -5(3) . . . . ?
C1 C8 C9 C11 -133(2) . . . . ?
C7 C8 C9 C10 177.1(17) . . . . ?
C1 C8 C9 C10 48(2) . . . . ?
C18 O1 C11 C12 165.7(17) . . . . ?
C18 O1 C11 C9 -3(3) . . . . ?
C8 C9 C11 O1 -14(3) . . . . ?
C10 C9 C11 O1 164.3(17) . . . . ?
C8 C9 C11 C12 179.3(19) . . . . ?
C10 C9 C11 C12 -2(3) . . . . ?
O1 C11 C12 C17 138.9(18) . . . . ?
C9 C11 C12 C17 -54(3) . . . . ?
O1 C11 C12 C13 -31(3) . . . . ?
C9 C11 C12 C13 136(2) . . . . ?
C17 C12 C13 C14 0(3) . . . . ?
C11 C12 C13 C14 170.1(19) . . . . ?
C12 C13 C14 C15 -4(3) . . . . ?
C13 C14 C15 C16 3(3) . . . . ?
C13 C14 C15 Br1 -175.2(14) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
Br1 C15 C16 C17 179.5(14) . . . . ?
C11 C12 C17 C16 -165(2) . . . . ?
C13 C12 C17 C16 5(3) . . . . ?
C15 C16 C17 C12 -5(3) . . . . ?
C11 O1 C18 C7 36(2) . . . . ?
C11 O1 C18 C23 159.7(16) . . . . ?
C11 O1 C18 C19 -87(2) . . . . ?
C8 C7 C18 O1 -55(2) . . . . ?
C8 C7 C18 C23 -174.1(18) . . . . ?
C8 C7 C18 C19 65(2) . . . . ?
O1 C18 C19 C20 -56(2) . . . . ?
C7 C18 C19 C20 -179.6(18) . . . . ?
C23 C18 C19 C20 56(2) . . . . ?
C18 C19 C20 C21 -52(2) . . . . ?
C19 C20 C21 C22 47(3) . . . . ?
C20 C21 C22 O2 124(3) . . . . ?
C20 C21 C22 C23 -52(3) . . . . ?
O2 C22 C23 C18 -123(2) . . . . ?
C21 C22 C23 C18 54(3) . . . . ?
O1 C18 C23 C22 63(2) . . . . ?
C7 C18 C23 C22 -174(2) . . . . ?
C19 C18 C23 C22 -51(2) . . . . ?

_refine_diff_density_max         1.000
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.125



