# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_PK338
_database_code_depnum_ccdc_archive 'CCDC 2225274'
loop_
_audit_author_name
_audit_author_address
'PALLAB KARJEE'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 Br N3 O2'
_chemical_formula_weight         430.34

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   16.8943(6)
_cell_length_b                   9.1586(3)
_cell_length_c                   13.1298(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2031.55(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.99

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    2.044
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            55848
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.224
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3560
_reflns_number_gt                2836
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.5549P] 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 
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3560
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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
Br01 Br 0.49010(5) 0.27647(8) 0.88025(9) 0.0742(3) Uani 1 1 d . . . . .
O002 O 0.5555(2) 0.1957(4) 0.3940(4) 0.0549(11) Uani 1 1 d . . . . .
O003 O 0.5203(3) 0.2947(5) 0.2106(4) 0.0610(12) Uani 1 1 d . . . . .
N004 N 0.3346(3) 0.1640(6) 0.2881(4) 0.0524(12) Uani 1 1 d . . . . .
N005 N 0.3417(3) 0.1878(5) 0.3984(3) 0.0487(11) Uani 1 1 d . . . . .
N006 N 0.4767(3) 0.2306(5) 0.3676(6) 0.0472(14) Uani 1 1 d . . . . .
C007 C 0.4217(3) 0.1447(6) 0.4289(4) 0.0458(12) Uani 1 1 d . . . . .
H007 H 0.429560 0.040460 0.415392 0.055 Uiso 1 1 calc R U . . .
C008 C 0.4334(3) 0.1752(6) 0.5406(4) 0.0436(12) Uani 1 1 d . . . . .
C009 C 0.4474(3) 0.0633(7) 0.6083(4) 0.0491(13) Uani 1 1 d . . . . .
H009 H 0.447046 -0.032749 0.585236 0.059 Uiso 1 1 calc R U . . .
C00A C 0.3793(4) 0.2822(6) 0.2350(5) 0.0503(13) Uani 1 1 d . . . . .
C00B C 0.4628(4) 0.2352(7) 0.7426(5) 0.0488(14) Uani 1 1 d . . . . .
C00C C 0.4621(4) 0.0918(7) 0.7106(5) 0.0532(13) Uani 1 1 d . . . . .
H00C H 0.471300 0.016032 0.756263 0.064 Uiso 1 1 calc R U . . .
C00D C 0.4456(4) 0.3482(7) 0.6777(5) 0.0552(14) Uani 1 1 d . . . . .
H00D H 0.443893 0.443844 0.701425 0.066 Uiso 1 1 calc R U . . .
C00E C 0.2485(4) 0.1676(9) 0.2725(5) 0.0688(18) Uani 1 1 d . . . . .
H00A H 0.233913 0.116319 0.210625 0.083 Uiso 1 1 calc R U . . .
H00B H 0.229446 0.267353 0.268359 0.083 Uiso 1 1 calc R U . . .
C00F C 0.4309(4) 0.3173(6) 0.5763(5) 0.0542(15) Uani 1 1 d . . . . .
H00F H 0.419141 0.392972 0.531536 0.065 Uiso 1 1 calc R U . . .
C00G C 0.4657(4) 0.2662(6) 0.2667(5) 0.0484(14) Uani 1 1 d . . . . .
C00H C 0.2837(4) 0.0821(9) 0.4394(5) 0.0711(19) Uani 1 1 d . . . . .
H00E H 0.267602 0.109104 0.507774 0.085 Uiso 1 1 calc R U . . .
H00G H 0.305857 -0.015582 0.440982 0.085 Uiso 1 1 calc R U . . .
C00I C 0.6651(4) 0.2904(6) 0.4915(5) 0.0544(15) Uani 1 1 d . . . . .
C00J C 0.3525(4) 0.4382(8) 0.2620(6) 0.0716(18) Uani 1 1 d . . . . .
H00H H 0.300183 0.454660 0.235815 0.107 Uiso 1 1 calc R U . . .
H00I H 0.388419 0.507410 0.232363 0.107 Uiso 1 1 calc R U . . .
H00J H 0.352150 0.449888 0.334677 0.107 Uiso 1 1 calc R U . . .
C00K C 0.6508(4) 0.2169(8) 0.5802(6) 0.0701(19) Uani 1 1 d . . . . .
H00K H 0.599983 0.183315 0.593886 0.084 Uiso 1 1 calc R U . . .
C00L C 0.7103(5) 0.1917(10) 0.6498(8) 0.084(2) Uani 1 1 d . . . . .
H00L H 0.699190 0.140542 0.709267 0.101 Uiso 1 1 calc R U . . .
C00M C 0.5994(4) 0.3279(7) 0.4196(6) 0.0674(18) Uani 1 1 d . . . . .
H00M H 0.564278 0.398525 0.450980 0.081 Uiso 1 1 calc R U . . .
H00N H 0.621117 0.371071 0.358143 0.081 Uiso 1 1 calc R U . . .
C00N C 0.3715(6) 0.2559(10) 0.1214(6) 0.080(2) Uani 1 1 d . . . . .
H00O H 0.382898 0.155393 0.106645 0.120 Uiso 1 1 calc R U . . .
H00P H 0.408102 0.317328 0.085552 0.120 Uiso 1 1 calc R U . . .
H00Q H 0.318475 0.278234 0.100134 0.120 Uiso 1 1 calc R U . . .
C00O C 0.2150(4) 0.0898(11) 0.3673(6) 0.092(2) Uani 1 1 d . . . . .
H00R H 0.171693 0.145099 0.396704 0.111 Uiso 1 1 calc R U . . .
H00S H 0.196197 -0.007274 0.350170 0.111 Uiso 1 1 calc R U . . .
C00P C 0.7409(5) 0.3382(10) 0.4729(8) 0.090(2) Uani 1 1 d . . . . .
H00T H 0.752384 0.387980 0.412974 0.108 Uiso 1 1 calc R U . . .
C00Q C 0.7845(6) 0.2403(10) 0.6329(9) 0.085(3) Uani 1 1 d . . . . .
H00U H 0.823885 0.225060 0.681266 0.102 Uiso 1 1 calc R U . . .
C00R C 0.8016(5) 0.3116(11) 0.5450(11) 0.106(3) Uani 1 1 d . . . . .
H00V H 0.852976 0.342841 0.532086 0.127 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
Br01 C00B 1.903(6) . ?
O002 N006 1.412(6) . ?
O002 C00M 1.460(8) . ?
O003 C00G 1.210(8) . ?
N004 C00E 1.470(8) . ?
N004 N005 1.470(6) . ?
N004 C00A 1.491(8) . ?
N005 C007 1.463(7) . ?
N005 C00H 1.479(8) . ?
N006 C00G 1.377(10) . ?
N006 C007 1.460(8) . ?
C007 C008 1.506(7) . ?
C008 C009 1.377(8) . ?
C008 C00F 1.384(8) . ?
C009 C00C 1.391(8) . ?
C00A C00N 1.517(10) . ?
C00A C00G 1.524(10) . ?
C00A C00J 1.541(9) . ?
C00B C00D 1.372(9) . ?
C00B C00C 1.379(9) . ?
C00D C00F 1.384(8) . ?
C00E C00O 1.543(11) . ?
C00H C00O 1.500(9) . ?
C00I C00K 1.366(10) . ?
C00I C00P 1.376(10) . ?
C00I C00M 1.497(10) . ?
C00K C00L 1.378(12) . ?
C00L C00Q 1.349(12) . ?
C00P C00R 1.416(14) . ?
C00Q C00R 1.357(16) . ?

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
N006 O002 C00M 110.4(4) . . ?
C00E N004 N005 102.4(5) . . ?
C00E N004 C00A 114.8(5) . . ?
N005 N004 C00A 108.2(4) . . ?
C007 N005 N004 107.7(4) . . ?
C007 N005 C00H 109.6(5) . . ?
N004 N005 C00H 102.0(4) . . ?
C00G N006 O002 114.7(5) . . ?
C00G N006 C007 124.9(5) . . ?
O002 N006 C007 110.0(5) . . ?
N006 C007 N005 107.0(4) . . ?
N006 C007 C008 110.7(5) . . ?
N005 C007 C008 109.7(4) . . ?
C009 C008 C00F 119.1(5) . . ?
C009 C008 C007 120.9(5) . . ?
C00F C008 C007 120.0(5) . . ?
C008 C009 C00C 120.9(5) . . ?
N004 C00A C00N 107.5(5) . . ?
N004 C00A C00G 106.7(5) . . ?
C00N C00A C00G 109.6(6) . . ?
N004 C00A C00J 114.7(5) . . ?
C00N C00A C00J 110.4(6) . . ?
C00G C00A C00J 107.9(5) . . ?
C00D C00B C00C 121.9(6) . . ?
C00D C00B Br01 119.4(4) . . ?
C00C C00B Br01 118.7(5) . . ?
C00B C00C C009 118.3(6) . . ?
C00B C00D C00F 118.8(6) . . ?
N004 C00E C00O 103.9(5) . . ?
C008 C00F C00D 120.8(6) . . ?
O003 C00G N006 122.2(6) . . ?
O003 C00G C00A 123.0(6) . . ?
N006 C00G C00A 114.5(5) . . ?
N005 C00H C00O 104.6(5) . . ?
C00K C00I C00P 118.2(7) . . ?
C00K C00I C00M 121.4(6) . . ?
C00P C00I C00M 120.3(7) . . ?
C00I C00K C00L 121.3(8) . . ?
C00Q C00L C00K 120.9(9) . . ?
O002 C00M C00I 109.4(5) . . ?
C00H C00O C00E 104.3(5) . . ?
C00I C00P C00R 120.0(9) . . ?
C00L C00Q C00R 119.7(9) . . ?
C00Q C00R C00P 119.9(8) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.048



