# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_mx10532
_database_code_depnum_ccdc_archive 'CCDC 2342120'
loop_
_audit_author_name
_audit_author_address
'yuan gao'
;sqnu
China
;
_audit_update_record             
;
2024-03-21 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2022-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 Br N O2'
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOBr
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7063(4)
_cell_length_b                   7.9223(4)
_cell_length_c                   32.7085(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1478.65(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5657
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      27.3020
_cell_measurement_theta_min      2.8170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            16468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.690
_diffrn_reflns_theta_min         2.491
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00  74.00   0.50    5.00    --  -14.80  45.00 150.00  356
  2  ω   -104.00  74.00   0.50    5.00    --  -14.80  45.00   0.00  356
  3  ω     29.00  73.00   0.50    5.00    --  -14.80  45.00  30.00   88
  4  ω     25.00  58.00   0.50    5.00    --  -14.80  45.00  90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1234657000
_diffrn_orient_matrix_UB_12      0.0101647000
_diffrn_orient_matrix_UB_13      -0.0012286000
_diffrn_orient_matrix_UB_21      -0.0145043000
_diffrn_orient_matrix_UB_22      -0.0884431000
_diffrn_orient_matrix_UB_23      0.0020838000
_diffrn_orient_matrix_UB_31      -0.0057201000
_diffrn_orient_matrix_UB_32      0.0091943000
_diffrn_orient_matrix_UB_33      0.0215356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                3399
_reflns_number_total             4006
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.4854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.01092(7) 0.41189(4) 0.19203(2) 0.03115(11) Uani 1 1 d . . . . .
O1 O 0.2692(5) 0.5403(3) 0.41361(8) 0.0336(7) Uani 1 1 d . . . . .
O2 O 0.1558(6) 0.7921(4) 0.39474(9) 0.0418(7) Uani 1 1 d . . . . .
N1 N 0.5708(6) 0.0406(4) 0.47513(10) 0.0327(8) Uani 1 1 d . . . . .
C1 C 0.5947(7) 0.5310(5) 0.34654(11) 0.0254(8) Uani 1 1 d . . . . .
H1 H 0.757724 0.541637 0.337486 0.030 Uiso 1 1 calc R U . . .
C2 C 0.5246(7) 0.6975(4) 0.36734(11) 0.0301(8) Uani 1 1 d . . . . .
H2A H 0.650636 0.733276 0.385250 0.036 Uiso 1 1 calc R U . . .
H2B H 0.504560 0.783734 0.346563 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3019(7) 0.6838(5) 0.39187(12) 0.0319(9) Uani 1 1 d . . . . .
C4 C 0.4308(6) 0.4060(5) 0.41090(10) 0.0261(7) Uani 1 1 d . . . . .
C5 C 0.4157(7) 0.2881(5) 0.44179(11) 0.0297(8) Uani 1 1 d . . . . .
H5 H 0.305560 0.300774 0.462528 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5669(7) 0.1493(5) 0.44172(11) 0.0280(8) Uani 1 1 d . . . . .
C7 C 0.7194(7) 0.1311(5) 0.40860(11) 0.0280(8) Uani 1 1 d . . . . .
H7 H 0.816802 0.037214 0.407155 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7271(6) 0.2507(5) 0.37808(12) 0.0289(8) Uani 1 1 d . . . . .
H8 H 0.831268 0.235498 0.356523 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5845(6) 0.3936(5) 0.37827(11) 0.0255(8) Uani 1 1 d . . . . .
C10 C 0.4443(5) 0.4975(4) 0.30902(11) 0.0232(7) Uani 1 1 d . . . . .
C11 C 0.2362(6) 0.4056(5) 0.31097(11) 0.0277(7) Uani 1 1 d . . . . .
H11 H 0.189537 0.358660 0.335725 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0983(7) 0.3833(5) 0.27668(11) 0.0265(8) Uani 1 1 d . . . . .
H12 H -0.041295 0.323152 0.278410 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1694(6) 0.4510(4) 0.23988(10) 0.0229(7) Uani 1 1 d . . . . .
C14 C 0.3768(7) 0.5412(5) 0.23681(11) 0.0277(8) Uani 1 1 d . . . . .
H14 H 0.424347 0.586192 0.211887 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5111(7) 0.5630(4) 0.27139(10) 0.0273(7) Uani 1 1 d . . . . .
H15 H 0.650566 0.623298 0.269498 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6956(8) -0.1174(5) 0.47356(12) 0.0364(10) Uani 1 1 d . . . . .
H16A H 0.606545 -0.197750 0.458020 0.055 Uiso 1 1 calc R U . . .
H16B H 0.718102 -0.159286 0.500817 0.055 Uiso 1 1 calc R U . . .
H16C H 0.845219 -0.100426 0.460791 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3812(8) 0.0482(5) 0.50467(13) 0.0378(10) Uani 1 1 d . . . . .
H17A H 0.371952 0.160002 0.515887 0.057 Uiso 1 1 calc R U . . .
H17B H 0.410245 -0.031223 0.526246 0.057 Uiso 1 1 calc R U . . .
H17C H 0.235942 0.020891 0.491416 0.057 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 C13 1.898(3) . ?
O1 C3 1.354(5) . ?
O1 C4 1.411(4) . ?
O2 C3 1.200(5) . ?
N1 C6 1.392(5) . ?
N1 C16 1.441(5) . ?
N1 C17 1.452(5) . ?
C1 H1 0.9800 . ?
C1 C2 1.537(5) . ?
C1 C9 1.505(5) . ?
C1 C10 1.521(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.507(6) . ?
C4 C5 1.379(5) . ?
C4 C9 1.385(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(5) . ?
C6 C7 1.397(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(5) . ?
C10 C11 1.394(4) . ?
C10 C15 1.389(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(5) . ?
C13 C14 1.386(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(5) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C3 O1 C4 120.7(3) . . ?
C6 N1 C16 121.2(3) . . ?
C6 N1 C17 119.0(3) . . ?
C16 N1 C17 115.3(3) . . ?
C2 C1 H1 107.9 . . ?
C9 C1 H1 107.9 . . ?
C9 C1 C2 107.8(3) . . ?
C9 C1 C10 114.1(3) . . ?
C10 C1 H1 107.9 . . ?
C10 C1 C2 111.1(3) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 113.1(3) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
O1 C3 C2 117.2(3) . . ?
O2 C3 O1 117.6(4) . . ?
O2 C3 C2 125.2(4) . . ?
C5 C4 O1 115.1(3) . . ?
C5 C4 C9 123.8(3) . . ?
C9 C4 O1 121.1(3) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 119.7(3) . . ?
N1 C6 C7 122.4(3) . . ?
C7 C6 C5 117.9(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.5(3) . . ?
C9 C8 H8 118.8 . . ?
C4 C9 C1 120.3(3) . . ?
C4 C9 C8 115.5(3) . . ?
C8 C9 C1 124.2(3) . . ?
C11 C10 C1 122.3(3) . . ?
C15 C10 C1 119.6(3) . . ?
C15 C10 C11 118.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 Br1 119.8(3) . . ?
C12 C13 C14 121.0(3) . . ?
C14 C13 Br1 119.2(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.9(4) . . ?
C14 C15 H15 119.1 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
Br1 C13 C14 C15 -177.4(3) . . . . ?
O1 C4 C5 C6 179.5(3) . . . . ?
O1 C4 C9 C1 4.7(5) . . . . ?
O1 C4 C9 C8 -176.9(3) . . . . ?
N1 C6 C7 C8 -173.3(4) . . . . ?
C1 C2 C3 O1 39.4(5) . . . . ?
C1 C2 C3 O2 -143.3(4) . . . . ?
C1 C10 C11 C12 177.2(3) . . . . ?
C1 C10 C15 C14 -177.7(3) . . . . ?
C2 C1 C9 C4 28.7(5) . . . . ?
C2 C1 C9 C8 -149.5(4) . . . . ?
C2 C1 C10 C11 -91.0(4) . . . . ?
C2 C1 C10 C15 87.5(4) . . . . ?
C3 O1 C4 C5 163.3(3) . . . . ?
C3 O1 C4 C9 -19.2(5) . . . . ?
C4 O1 C3 O2 178.4(3) . . . . ?
C4 O1 C3 C2 -4.1(5) . . . . ?
C4 C5 C6 N1 172.7(4) . . . . ?
C4 C5 C6 C7 -3.7(6) . . . . ?
C5 C4 C9 C1 -178.1(3) . . . . ?
C5 C4 C9 C8 0.3(5) . . . . ?
C5 C6 C7 C8 2.9(6) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C1 177.2(3) . . . . ?
C7 C8 C9 C4 -1.2(5) . . . . ?
C9 C1 C2 C3 -49.2(4) . . . . ?
C9 C1 C10 C11 31.1(5) . . . . ?
C9 C1 C10 C15 -150.4(3) . . . . ?
C9 C4 C5 C6 2.2(6) . . . . ?
C10 C1 C2 C3 76.5(4) . . . . ?
C10 C1 C9 C4 -95.2(4) . . . . ?
C10 C1 C9 C8 86.5(4) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C10 C15 C14 0.9(5) . . . . ?
C11 C12 C13 Br1 177.0(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C10 -0.1(5) . . . . ?
C15 C10 C11 C12 -1.3(5) . . . . ?
C16 N1 C6 C5 170.0(4) . . . . ?
C16 N1 C6 C7 -13.8(6) . . . . ?
C17 N1 C6 C5 14.9(6) . . . . ?
C17 N1 C6 C7 -168.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.145
_oxdiff_exptl_absorpt_empirical_full_min 0.628
