# 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_t_b
_audit_block_doi                 10.5517/ccdc.csd.cc1pzfps
_database_code_depnum_ccdc_archive 'CCDC 1578386'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.7b03185 2018
_audit_update_record             
;
2017-10-06 deposited with the CCDC.	2021-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br N3 O3'
_chemical_formula_weight         468.35

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.6515(12)
_cell_length_b                   8.034(2)
_cell_length_c                   12.082(3)
_cell_angle_alpha                81.886(8)
_cell_angle_beta                 88.585(9)
_cell_angle_gamma                73.865(9)
_cell_volume                     521.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9518
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      29.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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 APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3016
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_sigmaI/netI    0.1550
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         30.58
_reflns_number_total             2978
_reflns_number_gt                2254
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.031(15)
_refine_ls_number_reflns         2978
_refine_ls_number_parameters     271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.925
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.00531(7) 0.13039(6) 0.95792(6) 0.0317(3) Uani 1 1 d . . .
O1 O 0.1690(10) 0.2283(8) 0.4997(4) 0.0250(13) Uani 1 1 d . . .
O2 O 0.5730(10) 0.7878(8) 0.5422(4) 0.0240(13) Uani 1 1 d . . .
O3 O 0.3413(9) 0.8761(7) 0.6893(4) 0.0192(12) Uani 1 1 d . . .
N1 N 0.4620(11) 0.2340(8) 0.3697(4) 0.0144(12) Uani 1 1 d . . .
N2 N 0.1000(12) 0.7892(9) 0.4473(4) 0.0191(14) Uani 1 1 d . . .
H2A H 0.0654 0.8965 0.4116 0.023 Uiso 1 1 calc R . .
N3 N 0.6422(14) 0.3040(11) 0.3207(6) 0.0296(17) Uani 1 1 d . . .
C1 C 0.1396(14) 0.6504(10) 0.2724(5) 0.0162(15) Uani 1 1 d . . .
C2 C -0.0048(13) 0.5819(10) 0.2068(6) 0.0183(16) Uani 1 1 d . . .
H2B H -0.1277 0.5313 0.2395 0.022 Uiso 1 1 calc R . .
C3 C 0.0400(16) 0.5914(12) 0.0918(6) 0.030(2) Uani 1 1 d . . .
H3B H -0.0523 0.5442 0.0462 0.035 Uiso 1 1 calc R . .
C4 C 0.2158(16) 0.6681(11) 0.0429(6) 0.0241(18) Uani 1 1 d . . .
H4A H 0.2410 0.6753 -0.0355 0.029 Uiso 1 1 calc R . .
C5 C 0.3553(16) 0.7346(11) 0.1097(6) 0.0231(17) Uani 1 1 d . . .
H5A H 0.4766 0.7871 0.0772 0.028 Uiso 1 1 calc R . .
C6 C 0.3152(14) 0.7234(11) 0.2255(6) 0.0209(17) Uani 1 1 d . . .
H6A H 0.4115 0.7671 0.2713 0.025 Uiso 1 1 calc R . .
C7 C 0.0960(14) 0.6329(9) 0.3983(5) 0.0144(14) Uani 1 1 d . . .
H7A H -0.0656 0.6069 0.4140 0.017 Uiso 1 1 calc R . .
C8 C 0.3043(13) 0.4892(10) 0.4678(5) 0.0155(15) Uani 1 1 d . . .
H8A H 0.4680 0.5083 0.4467 0.019 Uiso 1 1 calc R . .
C9 C 0.2411(13) 0.5340(9) 0.5846(5) 0.0127(14) Uani 1 1 d . . .
H9A H 0.0874 0.4997 0.6062 0.015 Uiso 1 1 calc R . .
C10 C 0.1711(13) 0.7369(10) 0.5656(5) 0.0165(15) Uani 1 1 d . . .
H10A H 0.0267 0.7839 0.6128 0.020 Uiso 1 1 calc R . .
C11 C 0.4341(14) 0.4406(10) 0.6741(5) 0.0158(15) Uani 1 1 d . . .
C12 C 0.6756(14) 0.3545(10) 0.6491(6) 0.0173(15) Uani 1 1 d . . .
H12A H 0.7239 0.3585 0.5731 0.021 Uiso 1 1 calc R . .
C13 C 0.8484(15) 0.2627(11) 0.7323(6) 0.0200(16) Uani 1 1 d . . .
H13A H 1.0116 0.2037 0.7136 0.024 Uiso 1 1 calc R . .
C14 C 0.7758(16) 0.2596(10) 0.8434(5) 0.0214(17) Uani 1 1 d . . .
C15 C 0.5381(15) 0.3432(11) 0.8719(6) 0.0239(18) Uani 1 1 d . . .
H15A H 0.4921 0.3403 0.9482 0.029 Uiso 1 1 calc R . .
C16 C 0.3665(15) 0.4321(11) 0.7873(6) 0.0201(16) Uani 1 1 d . . .
H16A H 0.2022 0.4874 0.8064 0.024 Uiso 1 1 calc R . .
C17 C 0.7422(17) 0.1980(12) 0.2490(7) 0.0287(19) Uani 1 1 d . . .
H17A H 0.8728 0.2148 0.2016 0.034 Uiso 1 1 calc R . .
C18 C 0.6422(16) 0.0595(11) 0.2478(6) 0.0267(19) Uani 1 1 d . . .
H18A H 0.6884 -0.0311 0.2022 0.032 Uiso 1 1 calc R . .
C19 C 0.4588(15) 0.0814(11) 0.3281(6) 0.0208(16) Uani 1 1 d . . .
H19A H 0.3544 0.0084 0.3497 0.025 Uiso 1 1 calc R . .
C20 C 0.3045(13) 0.3093(10) 0.4512(5) 0.0149(15) Uani 1 1 d . . .
C21 C 0.3849(14) 0.8029(10) 0.5954(5) 0.0164(15) Uani 1 1 d . . .
C22 C 0.5360(15) 0.9403(12) 0.7288(7) 0.028(2) Uani 1 1 d . . .
H22A H 0.4641 1.0417 0.7688 0.033 Uiso 1 1 calc R . .
H22B H 0.6300 0.9784 0.6646 0.033 Uiso 1 1 calc R . .
C23 C 0.7071(17) 0.7919(15) 0.8077(7) 0.034(2) Uani 1 1 d . . .
H23A H 0.8384 0.8335 0.8359 0.051 Uiso 1 1 calc R . .
H23B H 0.7799 0.6929 0.7671 0.051 Uiso 1 1 calc R . .
H23C H 0.6124 0.7544 0.8707 0.051 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
Br1 C14 1.899(7) . ?
O1 C20 1.224(9) . ?
O2 C21 1.214(9) . ?
O3 C21 1.338(8) . ?
O3 C22 1.454(9) . ?
N1 N3 1.378(10) . ?
N1 C19 1.394(10) . ?
N1 C20 1.398(9) . ?
N2 C10 1.464(8) . ?
N2 C7 1.467(9) . ?
N2 H2A 0.8800 . ?
N3 C17 1.309(10) . ?
C1 C6 1.361(11) . ?
C1 C2 1.415(10) . ?
C1 C7 1.528(9) . ?
C2 C3 1.401(10) . ?
C2 H2B 0.9500 . ?
C3 C4 1.387(13) . ?
C3 H3B 0.9500 . ?
C4 C5 1.395(12) . ?
C4 H4A 0.9500 . ?
C5 C6 1.406(10) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.563(10) . ?
C7 H7A 1.0000 . ?
C8 C20 1.487(11) . ?
C8 C9 1.515(8) . ?
C8 H8A 1.0000 . ?
C9 C11 1.515(9) . ?
C9 C10 1.551(11) . ?
C9 H9A 1.0000 . ?
C10 C21 1.517(10) . ?
C10 H10A 1.0000 . ?
C11 C12 1.395(11) . ?
C11 C16 1.408(10) . ?
C12 C13 1.395(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.393(10) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(11) . ?
C15 C16 1.398(10) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.383(13) . ?
C17 H17A 0.9500 . ?
C18 C19 1.394(11) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C22 C23 1.533(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C21 O3 C22 116.5(6) . . ?
N3 N1 C19 111.7(6) . . ?
N3 N1 C20 123.1(6) . . ?
C19 N1 C20 125.2(6) . . ?
C10 N2 C7 108.7(6) . . ?
C10 N2 H2A 125.6 . . ?
C7 N2 H2A 125.6 . . ?
C17 N3 N1 103.8(7) . . ?
C6 C1 C2 121.1(6) . . ?
C6 C1 C7 121.6(6) . . ?
C2 C1 C7 117.2(7) . . ?
C3 C2 C1 117.6(8) . . ?
C3 C2 H2B 121.2 . . ?
C1 C2 H2B 121.2 . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3B 119.2 . . ?
C2 C3 H3B 119.2 . . ?
C3 C4 C5 119.5(7) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 119.5(8) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C1 C6 C5 120.6(7) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
N2 C7 C1 113.3(6) . . ?
N2 C7 C8 101.3(5) . . ?
C1 C7 C8 113.6(5) . . ?
N2 C7 H7A 109.4 . . ?
C1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C20 C8 C9 115.1(6) . . ?
C20 C8 C7 112.3(5) . . ?
C9 C8 C7 100.4(5) . . ?
C20 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C8 C9 C11 115.4(6) . . ?
C8 C9 C10 102.4(6) . . ?
C11 C9 C10 117.1(5) . . ?
C8 C9 H9A 107.1 . . ?
C11 C9 H9A 107.1 . . ?
C10 C9 H9A 107.1 . . ?
N2 C10 C21 111.9(7) . . ?
N2 C10 C9 105.8(5) . . ?
C21 C10 C9 111.1(6) . . ?
N2 C10 H10A 109.3 . . ?
C21 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C12 C11 C16 117.9(6) . . ?
C12 C11 C9 122.7(6) . . ?
C16 C11 C9 119.3(6) . . ?
C11 C12 C13 122.0(7) . . ?
C11 C12 H12A 119.0 . . ?
C13 C12 H12A 119.0 . . ?
C14 C13 C12 118.4(7) . . ?
C14 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C15 C14 C13 121.5(7) . . ?
C15 C14 Br1 119.3(5) . . ?
C13 C14 Br1 119.1(6) . . ?
C14 C15 C16 119.3(6) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
C15 C16 C11 120.9(7) . . ?
C15 C16 H16A 119.6 . . ?
C11 C16 H16A 119.6 . . ?
N3 C17 C18 114.4(8) . . ?
N3 C17 H17A 122.8 . . ?
C18 C17 H17A 122.8 . . ?
C17 C18 C19 105.1(6) . . ?
C17 C18 H18A 127.4 . . ?
C19 C18 H18A 127.4 . . ?
N1 C19 C18 104.9(7) . . ?
N1 C19 H19A 127.5 . . ?
C18 C19 H19A 127.5 . . ?
O1 C20 N1 118.8(6) . . ?
O1 C20 C8 124.5(7) . . ?
N1 C20 C8 116.6(7) . . ?
O2 C21 O3 124.5(6) . . ?
O2 C21 C10 124.4(6) . . ?
O3 C21 C10 111.1(6) . . ?
O3 C22 C23 108.4(8) . . ?
O3 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O3 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.720
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.720
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.111
