# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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#######################################################################

data_cxy1226_0m
_database_code_depnum_ccdc_archive 'CCDC 2046371'
loop_
_audit_author_name
_audit_author_address
'Jun WANG'
;Hong Kong Baptist University
Hong Kong
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_audit_creation_date             2020-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Br N O2'
_chemical_formula_sum            'C16 H16 Br N O2'
_chemical_formula_weight         334.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.1119(7)
_cell_length_b                   4.7233(3)
_cell_length_c                   12.2988(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.469(2)
_cell_angle_gamma                90
_cell_volume                     703.57(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.428
_shelx_estimated_absorpt_T_min   0.403
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1233 before and 0.0709 after correction. The Ratio of minimum to maximum transmission is 0.5090. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18512
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.758
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4205
_reflns_number_total             4367
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+0.2388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0708
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.72084(2) 0.60680(6) 0.80188(2) 0.01818(9) Uani 1 1 d . . . . .
O1 O 0.52472(15) 0.4126(4) 0.55032(17) 0.0135(4) Uani 1 1 d . . . . .
H1 H 0.487035 0.274507 0.528256 0.020 Uiso 1 1 calc GR . . . .
O2 O 0.64656(17) 0.4045(5) 0.04031(16) 0.0184(4) Uani 1 1 d . . . . .
N1 N 0.69696(19) 0.4923(5) 0.37588(19) 0.0129(4) Uani 1 1 d . . . . .
H1A H 0.658840 0.337819 0.389334 0.015 Uiso 1 1 calc R . . . .
C1 C 0.9075(2) 0.0389(6) 0.0710(3) 0.0203(6) Uani 1 1 d . . . . .
H1B H 0.951417 -0.088215 0.029968 0.024 Uiso 1 1 calc R . . . .
C2 C 0.8092(2) 0.1386(7) 0.0284(2) 0.0183(5) Uani 1 1 d . . . . .
H2 H 0.785950 0.081763 -0.042194 0.022 Uiso 1 1 calc R . . . .
C3 C 0.7438(2) 0.3232(6) 0.0892(2) 0.0136(5) Uani 1 1 d . . . . .
C4 C 0.77527(18) 0.4049(6) 0.19349(19) 0.0113(5) Uani 1 1 d . . . . .
C5 C 0.70053(17) 0.5887(7) 0.26316(17) 0.0114(4) Uani 1 1 d . . . . .
H5 H 0.728650 0.787713 0.261775 0.014 Uiso 1 1 calc R . . . .
C6 C 0.74793(17) 0.6219(7) 0.46267(17) 0.0107(4) Uani 1 1 d . . . . .
C7 C 0.71592(19) 0.5462(5) 0.5699(2) 0.0097(4) Uani 1 1 d . . . . .
C8 C 0.7651(2) 0.6881(5) 0.6567(2) 0.0122(5) Uani 1 1 d . . . . .
C9 C 0.8462(2) 0.8947(6) 0.6437(2) 0.0141(5) Uani 1 1 d . . . . .
H9 H 0.878090 0.988557 0.704688 0.017 Uiso 1 1 calc R . . . .
C10 C 0.94257(19) 0.1245(8) 0.1742(2) 0.0183(5) Uani 1 1 d . . . . .
H10 H 1.010891 0.059283 0.203266 0.022 Uiso 1 1 calc R . . . .
C11 C 0.8765(2) 0.3060(6) 0.2339(2) 0.0138(5) Uani 1 1 d . . . . .
H11 H 0.900624 0.364700 0.304066 0.017 Uiso 1 1 calc R . . . .
C12 C 0.8788(2) 0.9585(5) 0.5385(2) 0.0151(5) Uani 1 1 d . . . . .
H12 H 0.934732 1.096422 0.527563 0.018 Uiso 1 1 calc R . . . .
C13 C 0.8316(2) 0.8252(6) 0.4490(2) 0.0129(5) Uani 1 1 d . . . . .
H13 H 0.855902 0.871610 0.377946 0.015 Uiso 1 1 calc R . . . .
C14 C 0.6326(2) 0.3147(5) 0.5846(2) 0.0110(4) Uani 1 1 d . . . . .
H14A H 0.653971 0.147463 0.541104 0.013 Uiso 1 1 calc R . . . .
H14B H 0.630484 0.257808 0.662050 0.013 Uiso 1 1 calc R . . . .
C15 C 0.58384(18) 0.5837(8) 0.21515(19) 0.0161(5) Uani 1 1 d . . . . .
H15A H 0.548649 0.399267 0.230979 0.019 Uiso 1 1 calc R . . . .
H15B H 0.538940 0.734496 0.249040 0.019 Uiso 1 1 calc R . . . .
C16 C 0.5877(2) 0.6292(8) 0.0932(2) 0.0170(5) Uani 1 1 d . . . . .
H16A H 0.511444 0.638478 0.063772 0.020 Uiso 1 1 calc R . . . .
H16B H 0.624310 0.812015 0.077676 0.020 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 C8 1.907(3) . ?
O1 H1 0.8400 . ?
O1 C14 1.446(3) . ?
O2 C3 1.373(3) . ?
O2 C16 1.437(4) . ?
N1 H1A 0.8800 . ?
N1 C5 1.460(3) . ?
N1 C6 1.373(3) . ?
C1 H1B 0.9500 . ?
C1 C2 1.379(4) . ?
C1 C10 1.395(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(4) . ?
C3 C4 1.390(3) . ?
C4 C5 1.523(4) . ?
C4 C11 1.400(3) . ?
C5 H5 1.0000 . ?
C5 C15 1.527(3) . ?
C6 C7 1.423(3) . ?
C6 C13 1.407(4) . ?
C7 C8 1.391(3) . ?
C7 C14 1.500(3) . ?
C8 C9 1.395(4) . ?
C9 H9 0.9500 . ?
C9 C12 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C14 O1 H1 109.5 . . ?
C3 O2 C16 115.8(2) . . ?
C5 N1 H1A 117.2 . . ?
C6 N1 H1A 117.2 . . ?
C6 N1 C5 125.6(2) . . ?
C2 C1 H1B 119.9 . . ?
C2 C1 C10 120.1(3) . . ?
C10 C1 H1B 119.9 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
O2 C3 C2 115.4(2) . . ?
O2 C3 C4 123.6(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 C11 117.9(2) . . ?
C11 C4 C5 120.9(2) . . ?
N1 C5 C4 112.3(2) . . ?
N1 C5 H5 108.8 . . ?
N1 C5 C15 109.13(19) . . ?
C4 C5 H5 108.8 . . ?
C4 C5 C15 109.0(2) . . ?
C15 C5 H5 108.8 . . ?
N1 C6 C7 119.0(2) . . ?
N1 C6 C13 122.1(2) . . ?
C13 C6 C7 119.0(2) . . ?
C6 C7 C14 118.9(2) . . ?
C8 C7 C6 118.2(2) . . ?
C8 C7 C14 122.9(2) . . ?
C7 C8 Br1 119.97(18) . . ?
C7 C8 C9 123.2(2) . . ?
C9 C8 Br1 116.9(2) . . ?
C8 C9 H9 121.2 . . ?
C12 C9 C8 117.7(2) . . ?
C12 C9 H9 121.2 . . ?
C1 C10 H10 120.4 . . ?
C11 C10 C1 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C4 C11 H11 119.1 . . ?
C10 C11 C4 121.7(3) . . ?
C10 C11 H11 119.1 . . ?
C9 C12 H12 119.3 . . ?
C13 C12 C9 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C6 C13 H13 119.7 . . ?
C12 C13 C6 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
O1 C14 C7 109.82(19) . . ?
O1 C14 H14A 109.7 . . ?
O1 C14 H14B 109.7 . . ?
C7 C14 H14A 109.7 . . ?
C7 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C5 C15 H15A 109.6 . . ?
C5 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C5 110.15(19) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
O2 C16 C15 111.3(3) . . ?
O2 C16 H16A 109.4 . . ?
O2 C16 H16B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 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
Br1 C8 C9 C12 -179.46(19) . . . . ?
O2 C3 C4 C5 1.6(4) . . . . ?
O2 C3 C4 C11 179.7(2) . . . . ?
N1 C5 C15 C16 -169.4(3) . . . . ?
N1 C6 C7 C8 -177.3(2) . . . . ?
N1 C6 C7 C14 3.7(3) . . . . ?
N1 C6 C13 C12 177.9(3) . . . . ?
C1 C2 C3 O2 -178.6(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C10 C11 C4 0.2(4) . . . . ?
C2 C1 C10 C11 1.2(5) . . . . ?
C2 C3 C4 C5 -175.5(3) . . . . ?
C2 C3 C4 C11 2.6(4) . . . . ?
C3 O2 C16 C15 -44.6(3) . . . . ?
C3 C4 C5 N1 137.5(2) . . . . ?
C3 C4 C5 C15 16.4(4) . . . . ?
C3 C4 C11 C10 -2.1(4) . . . . ?
C4 C5 C15 C16 -46.5(4) . . . . ?
C5 N1 C6 C7 164.8(2) . . . . ?
C5 N1 C6 C13 -15.8(4) . . . . ?
C5 C4 C11 C10 176.0(3) . . . . ?
C5 C15 C16 O2 62.8(4) . . . . ?
C6 N1 C5 C4 105.8(3) . . . . ?
C6 N1 C5 C15 -133.2(3) . . . . ?
C6 C7 C8 Br1 177.33(18) . . . . ?
C6 C7 C8 C9 -1.9(4) . . . . ?
C6 C7 C14 O1 -71.4(3) . . . . ?
C7 C6 C13 C12 -2.7(4) . . . . ?
C7 C8 C9 C12 -0.3(4) . . . . ?
C8 C7 C14 O1 109.7(3) . . . . ?
C8 C9 C12 C13 0.9(4) . . . . ?
C9 C12 C13 C6 0.6(4) . . . . ?
C10 C1 C2 C3 -0.7(4) . . . . ?
C11 C4 C5 N1 -40.6(3) . . . . ?
C11 C4 C5 C15 -161.6(3) . . . . ?
C13 C6 C7 C8 3.3(4) . . . . ?
C13 C6 C7 C14 -175.7(2) . . . . ?
C14 C7 C8 Br1 -3.8(3) . . . . ?
C14 C7 C8 C9 177.1(2) . . . . ?
C16 O2 C3 C2 -170.0(2) . . . . ?
C16 O2 C3 C4 12.8(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
