# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_KB386_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2247430'
loop_
_audit_author_name
_audit_author_address
'Ramaraju Korivi'
;SRM UNIVERSITY AP
India
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.0055(8)
_cell_length_b                   6.7488(6)
_cell_length_c                   15.1767(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.408(4)
_cell_angle_gamma                90
_cell_volume                     700.77(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5939
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.39

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13801
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4243
_reflns_number_gt                3733
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.989

_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       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0998P)²+0.0028P] 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 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C7 C 0.6161(3) 0.5547(3) 0.46177(13) 0.0433(4) Uani 1 1 d . . . . .
H7 H 0.533858 0.468536 0.483817 0.052 Uiso 1 1 calc R U . . .
C8 C 0.5602(2) 0.7016(3) 0.17499(11) 0.0365(3) Uani 1 1 d . . . . .
C9 C 0.6268(2) 0.6931(3) 0.08896(11) 0.0358(3) Uani 1 1 d . . . . .
C10 C 0.5174(3) 0.6919(4) 0.00124(13) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.381929 0.702178 -0.010756 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6172(4) 0.6749(4) -0.06794(13) 0.0518(5) Uani 1 1 d . . . . .
H11 H 0.547734 0.673716 -0.127500 0.062 Uiso 1 1 calc R U . . .
C12 C 0.8188(4) 0.6596(4) -0.04961(14) 0.0558(6) Uani 1 1 d . . . . .
H12 H 0.882312 0.645463 -0.097126 0.067 Uiso 1 1 calc R U . . .
C13 C 0.9286(3) 0.6649(4) 0.03849(14) 0.0501(5) Uani 1 1 d . . . . .
H13 H 1.064333 0.657609 0.050528 0.060 Uiso 1 1 calc R U . . .
C14 C 0.8284(2) 0.6815(3) 0.10762(11) 0.0361(3) Uani 1 1 d . . . . .
C15 C 0.9071(2) 0.6872(3) 0.20754(11) 0.0352(3) Uani 1 1 d . . . . .
H15 H 0.982762 0.808980 0.223747 0.042 Uiso 1 1 calc R U . . .
C16 C 1.0326(3) 0.5070(3) 0.24436(13) 0.0413(4) Uani 1 1 d . . . . .
H16A H 1.144148 0.500051 0.216108 0.050 Uiso 1 1 calc R U . . .
H16B H 1.081395 0.522825 0.308793 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9220(3) 0.3230(3) 0.22752(14) 0.0465(4) Uani 1 1 d . . . . .
O1 O 0.7568(2) 0.6825(3) 0.61159(9) 0.0498(4) Uani 1 1 d . . . . .
O2 O 0.39424(19) 0.7117(3) 0.18702(10) 0.0524(4) Uani 1 1 d . . . . .
N1 N 0.7275(2) 0.6956(3) 0.24221(9) 0.0343(3) Uani 1 1 d . . . . .
N2 N 0.8352(4) 0.1804(4) 0.21480(19) 0.0726(7) Uani 1 1 d . . . . .
C1 C 0.6418(4) 0.5491(5) 0.65009(15) 0.0605(7) Uani 1 1 d . . . . .
H1A H 0.505963 0.579515 0.628465 0.091 Uiso 1 1 calc R U . . .
H1B H 0.674711 0.561314 0.714607 0.091 Uiso 1 1 calc R U . . .
H1C H 0.666836 0.416004 0.633315 0.091 Uiso 1 1 calc R U . . .
C2 C 0.7423(2) 0.6775(3) 0.52040(11) 0.0365(3) Uani 1 1 d . . . . .
C3 C 0.8624(3) 0.8065(3) 0.48657(13) 0.0431(4) Uani 1 1 d . . . . .
H3 H 0.948129 0.888067 0.525815 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8561(3) 0.8152(3) 0.39515(13) 0.0407(4) Uani 1 1 d . . . . .
H4 H 0.935980 0.903989 0.373099 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7308(2) 0.6919(3) 0.33582(10) 0.0339(3) Uani 1 1 d . . . . .
C6 C 0.6129(3) 0.5609(3) 0.36995(12) 0.0416(4) Uani 1 1 d . . . . .
H6 H 0.530480 0.476013 0.330948 0.050 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
C7 C2 1.386(3) . ?
C7 C6 1.390(3) . ?
C7 H7 0.9300 . ?
C8 O2 1.217(2) . ?
C8 N1 1.379(2) . ?
C8 C9 1.479(2) . ?
C9 C14 1.382(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.499(2) . ?
C15 N1 1.466(2) . ?
C15 C16 1.534(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.457(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.133(3) . ?
O1 C2 1.3660(19) . ?
O1 C1 1.416(3) . ?
N1 C5 1.4160(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.384(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 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 C7 C6 119.77(17) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 N1 125.30(16) . . ?
O2 C8 C9 128.84(15) . . ?
N1 C8 C9 105.85(14) . . ?
C14 C9 C10 121.75(17) . . ?
C14 C9 C8 108.88(14) . . ?
C10 C9 C8 129.36(16) . . ?
C9 C10 C11 117.62(18) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C12 C11 C10 120.88(19) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.6(2) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C9 C14 C13 120.72(17) . . ?
C9 C14 C15 110.10(15) . . ?
C13 C14 C15 129.18(17) . . ?
N1 C15 C14 101.93(13) . . ?
N1 C15 C16 111.63(15) . . ?
C14 C15 C16 113.94(16) . . ?
N1 C15 H15 109.7 . . ?
C14 C15 H15 109.7 . . ?
C16 C15 H15 109.7 . . ?
C17 C16 C15 111.76(15) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 179.5(3) . . ?
C2 O1 C1 118.50(17) . . ?
C8 N1 C5 124.82(14) . . ?
C8 N1 C15 113.21(13) . . ?
C5 N1 C15 121.95(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.19(16) . . ?
O1 C2 C7 124.30(16) . . ?
C3 C2 C7 119.51(16) . . ?
C4 C3 C2 120.61(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.33(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.96(15) . . ?
C6 C5 N1 120.29(15) . . ?
C4 C5 N1 120.73(15) . . ?
C5 C6 C7 120.81(16) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?

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
O2 C8 C9 C14 -179.7(2) . . . . ?
N1 C8 C9 C14 0.3(2) . . . . ?
O2 C8 C9 C10 -0.9(4) . . . . ?
N1 C8 C9 C10 179.0(2) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C9 C10 C11 -177.4(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C10 C9 C14 C13 -1.1(3) . . . . ?
C8 C9 C14 C13 177.78(18) . . . . ?
C10 C9 C14 C15 179.65(19) . . . . ?
C8 C9 C14 C15 -1.5(2) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C12 C13 C14 C15 178.9(2) . . . . ?
C9 C14 C15 N1 2.02(19) . . . . ?
C13 C14 C15 N1 -177.2(2) . . . . ?
C9 C14 C15 C16 122.43(18) . . . . ?
C13 C14 C15 C16 -56.8(3) . . . . ?
N1 C15 C16 C17 54.1(2) . . . . ?
C14 C15 C16 C17 -60.7(2) . . . . ?
O2 C8 N1 C5 2.8(3) . . . . ?
C9 C8 N1 C5 -177.12(16) . . . . ?
O2 C8 N1 C15 -179.0(2) . . . . ?
C9 C8 N1 C15 1.1(2) . . . . ?
C14 C15 N1 C8 -1.91(19) . . . . ?
C16 C15 N1 C8 -123.91(18) . . . . ?
C14 C15 N1 C5 176.38(16) . . . . ?
C16 C15 N1 C5 54.4(2) . . . . ?
C1 O1 C2 C3 -178.0(2) . . . . ?
C1 O1 C2 C7 2.5(3) . . . . ?
C6 C7 C2 O1 -179.88(19) . . . . ?
C6 C7 C2 C3 0.6(3) . . . . ?
O1 C2 C3 C4 -178.85(18) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 N1 -178.13(19) . . . . ?
C8 N1 C5 C6 48.1(3) . . . . ?
C15 N1 C5 C6 -129.9(2) . . . . ?
C8 N1 C5 C4 -133.7(2) . . . . ?
C15 N1 C5 C4 48.2(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
N1 C5 C6 C7 179.46(18) . . . . ?
C2 C7 C6 C5 -1.6(3) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_KB925_0m
_database_code_depnum_ccdc_archive 'CCDC 2306999'
loop_
_audit_author_name
_audit_author_address
'Ramaraju Korivi'
;SRM University AP
India
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 Br N O'
_chemical_formula_sum            'C21 H14 Br N O'
_chemical_formula_weight         376.24

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.7224(7)
_cell_length_b                   10.5046(6)
_cell_length_c                   14.0815(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.875(3)
_cell_angle_gamma                90
_cell_volume                     1683.39(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.445
_cell_measurement_theta_max      26.0435

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.448
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26432
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             5056
_reflns_number_gt                3301
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0400P)²+0.9045P] 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_number_reflns         5056
_refine_ls_number_parameters     236
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.018
_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 0.82827(19) 0.4667(2) 0.75434(16) 0.0487(5) Uani 1 1 d . . . . .
C2 C 0.7182(2) 0.4198(3) 0.7122(2) 0.0633(6) Uani 1 1 d . . . . .
H2 H 0.696038 0.339191 0.728330 0.076 Uiso 1 1 calc R U . . .
C3 C 0.6413(2) 0.4947(2) 0.64534(19) 0.0598(6) Uani 1 1 d . . . . .
H3 H 0.566537 0.464372 0.616159 0.072 Uiso 1 1 calc R U . . .
C4 C 0.67481(19) 0.6139(2) 0.62181(15) 0.0444(5) Uani 1 1 d . . . . .
C5 C 0.7840(2) 0.6601(2) 0.66679(16) 0.0479(5) Uani 1 1 d . . . . .
H5 H 0.805639 0.741763 0.652491 0.057 Uiso 1 1 calc R U . . .
C6 C 0.86202(19) 0.5857(2) 0.73321(16) 0.0488(5) Uani 1 1 d . . . . .
H6 H 0.936423 0.616304 0.763082 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4952(2) 0.7370(2) 0.57274(17) 0.0537(5) Uani 1 1 d . . . . .
C8 C 0.4210(2) 0.8188(2) 0.49950(17) 0.0541(5) Uani 1 1 d . . . . .
C9 C 0.3137(3) 0.8612(3) 0.5150(2) 0.0748(8) Uani 1 1 d . . . . .
H9 H 0.291680 0.838416 0.571903 0.090 Uiso 1 1 calc R U . . .
C10 C 0.2414(3) 0.9359(4) 0.4470(3) 0.0897(10) Uani 1 1 d . . . . .
H10 H 0.169755 0.962816 0.457213 0.108 Uiso 1 1 calc R U . . .
C11 C 0.2743(3) 0.9717(3) 0.3629(3) 0.0869(10) Uani 1 1 d . . . . .
H11 H 0.224837 1.023357 0.317310 0.104 Uiso 1 1 calc R U . . .
C12 C 0.3792(3) 0.9320(3) 0.3461(2) 0.0743(8) Uani 1 1 d . . . . .
H12 H 0.400386 0.957069 0.289356 0.089 Uiso 1 1 calc R U . . .
C13 C 0.4547(2) 0.8536(2) 0.41427(18) 0.0560(6) Uani 1 1 d . . . . .
C14 C 0.5621(2) 0.8034(3) 0.39831(17) 0.0577(6) Uani 1 1 d . . . . .
H14 H 0.585853 0.826801 0.342325 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6290(2) 0.7235(2) 0.46210(15) 0.0490(5) Uani 1 1 d . . . . .
C16 C 0.7344(2) 0.6621(3) 0.44114(16) 0.0561(6) Uani 1 1 d . . . . .
C17 C 0.8303(3) 0.7352(3) 0.4345(2) 0.0783(8) Uani 1 1 d D . . . .
H17 H 0.830473 0.822309 0.446358 0.094 Uiso 1 1 calc R U . A 1
C20 C 0.8333(4) 0.4784(4) 0.4013(3) 0.1056(14) Uani 1 1 d D . . . .
H20 H 0.832808 0.391630 0.388070 0.127 Uiso 1 1 calc R U . B 1
C21 C 0.7366(3) 0.5330(3) 0.4252(2) 0.0760(8) Uani 1 1 d . . . . .
H21 H 0.673250 0.482547 0.430491 0.091 Uiso 1 1 calc R U . . .
N1 N 0.59664(16) 0.69003(18) 0.54895(12) 0.0465(4) Uani 1 1 d . . . . .
O1 O 0.47297(18) 0.7081(2) 0.65033(14) 0.0766(6) Uani 1 1 d . . . . .
Br1 Br 0.93738(2) 0.36456(3) 0.84484(2) 0.07397(14) Uani 1 1 d . . . . .
C18 C 0.9260(6) 0.6784(10) 0.4103(10) 0.104(2) Uani 0.89(4) 1 d D U P C 1
H18 H 0.988837 0.728537 0.403267 0.125 Uiso 0.89(4) 1 calc R U P C 1
C19 C 0.9297(8) 0.5490(9) 0.3965(7) 0.104(2) Uani 0.89(4) 1 d D U P C 1
H19 H 0.996118 0.510478 0.384272 0.124 Uiso 0.89(4) 1 calc R U P C 1
C18D C 0.939(3) 0.691(8) 0.426(8) 0.100(7) Uani 0.11(4) 1 d D U P C 2
H18D H 1.012962 0.727087 0.444692 0.120 Uiso 0.11(4) 1 calc R U P C 2
C19D C 0.903(6) 0.575(6) 0.380(5) 0.102(7) Uani 0.11(4) 1 d D U P C 2
H19D H 0.931922 0.560585 0.324613 0.123 Uiso 0.11(4) 1 calc R U P C 2


_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 1.365(3) . ?
C1 C2 1.375(3) . ?
C1 Br1 1.905(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 N1 1.442(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.221(3) . ?
C7 N1 1.400(3) . ?
C7 C8 1.459(3) . ?
C8 C13 1.399(4) . ?
C8 C9 1.399(4) . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.432(4) . ?
C14 C15 1.337(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.409(3) . ?
C15 C16 1.484(3) . ?
C16 C21 1.377(4) . ?
C16 C17 1.383(4) . ?
C17 C18 1.384(6) . ?
C17 C18D 1.39(2) . ?
C17 H17 0.9300 . ?
C20 C19 1.366(7) . ?
C20 C21 1.382(5) . ?
C20 C19D 1.39(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C18 C19 1.375(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C18D C19D 1.39(2) . ?
C18D H18D 0.9300 . ?
C19D H19D 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
C6 C1 C2 121.7(2) . . ?
C6 C1 Br1 118.58(17) . . ?
C2 C1 Br1 119.76(18) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 N1 119.70(19) . . ?
C3 C4 N1 120.4(2) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 N1 120.2(2) . . ?
O1 C7 C8 124.0(2) . . ?
N1 C7 C8 115.8(2) . . ?
C13 C8 C9 120.0(2) . . ?
C13 C8 C7 121.1(2) . . ?
C9 C8 C7 118.9(2) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 118.5(3) . . ?
C8 C13 C14 118.6(2) . . ?
C12 C13 C14 122.8(2) . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 N1 120.2(2) . . ?
C14 C15 C16 121.4(2) . . ?
N1 C15 C16 118.32(19) . . ?
C21 C16 C17 119.2(3) . . ?
C21 C16 C15 120.7(3) . . ?
C17 C16 C15 120.1(3) . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 C18D 127(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C20 C21 121.5(5) . . ?
C21 C20 C19D 108(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C20 119.8(4) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C7 N1 C15 122.73(19) . . ?
C7 N1 C4 117.14(17) . . ?
C15 N1 C4 119.88(18) . . ?
C19 C18 C17 121.0(8) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 118.4(8) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19D C18D C17 99(5) . . ?
C19D C18D H18D 130.4 . . ?
C17 C18D H18D 130.4 . . ?
C18D C19D C20 132(7) . . ?
C18D C19D H19D 114.1 . . ?
C20 C19D H19D 114.1 . . ?

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 1.3(4) . . . . ?
Br1 C1 C2 C3 -178.8(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C2 C3 C4 N1 177.3(2) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
N1 C4 C5 C6 -176.81(19) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
Br1 C1 C6 C5 179.25(16) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
O1 C7 C8 C13 176.6(3) . . . . ?
N1 C7 C8 C13 -4.0(3) . . . . ?
O1 C7 C8 C9 -4.2(4) . . . . ?
N1 C7 C8 C9 175.2(2) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C10 -178.8(3) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C7 C8 C13 C12 179.6(2) . . . . ?
C9 C8 C13 C14 -176.9(2) . . . . ?
C7 C8 C13 C14 2.3(4) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C11 C12 C13 C14 176.5(3) . . . . ?
C8 C13 C14 C15 0.9(4) . . . . ?
C12 C13 C14 C15 -176.4(3) . . . . ?
C13 C14 C15 N1 -2.1(4) . . . . ?
C13 C14 C15 C16 174.2(2) . . . . ?
C14 C15 C16 C21 -111.9(3) . . . . ?
N1 C15 C16 C21 64.5(3) . . . . ?
C14 C15 C16 C17 66.1(3) . . . . ?
N1 C15 C16 C17 -117.5(3) . . . . ?
C21 C16 C17 C18 1.2(7) . . . . ?
C15 C16 C17 C18 -176.9(7) . . . . ?
C21 C16 C17 C18D -9(6) . . . . ?
C15 C16 C17 C18D 173(6) . . . . ?
C17 C16 C21 C20 -1.1(4) . . . . ?
C15 C16 C21 C20 177.0(3) . . . . ?
C19 C20 C21 C16 2.5(7) . . . . ?
C19D C20 C21 C16 -11(3) . . . . ?
O1 C7 N1 C15 -177.7(2) . . . . ?
C8 C7 N1 C15 2.9(3) . . . . ?
O1 C7 N1 C4 -3.5(3) . . . . ?
C8 C7 N1 C4 177.1(2) . . . . ?
C14 C15 N1 C7 0.1(3) . . . . ?
C16 C15 N1 C7 -176.3(2) . . . . ?
C14 C15 N1 C4 -174.0(2) . . . . ?
C16 C15 N1 C4 9.6(3) . . . . ?
C5 C4 N1 C7 -112.1(2) . . . . ?
C3 C4 N1 C7 69.0(3) . . . . ?
C5 C4 N1 C15 62.3(3) . . . . ?
C3 C4 N1 C15 -116.7(2) . . . . ?
C16 C17 C18 C19 -2.7(17) . . . . ?
C21 C20 C19 C18 -3.9(15) . . . . ?
C17 C18 C19 C20 4(2) . . . . ?
C16 C17 C18D C19D 27(11) . . . . ?
C17 C18D C19D C20 -49(14) . . . . ?
C21 C20 C19D C18D 44(11) . . . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.045



