# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_mx8881
_database_code_depnum_ccdc_archive 'CCDC 2044653'
loop_
_audit_author_name
_audit_author_address
'wang man'
;University
China
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;
_audit_creation_date             2020-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 Br N O3'
_chemical_formula_sum            'C19 H16 Br N O3'
_chemical_formula_weight         386.24
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.6894(4)
_cell_length_b                   15.9729(5)
_cell_length_c                   11.2283(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.917(4)
_cell_angle_gamma                90
_cell_volume                     1709.43(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8911
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.7880
_cell_measurement_theta_min      2.1710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85013
_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    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15300
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.864
_diffrn_reflns_theta_min         2.137
_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 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -44.00   0.50    3.00    --    5.00  45.00  30.00   80
  2  ω   -101.00  26.00   0.50    3.00    --  -11.60  45.00 112.27  254
  3  ω    -78.00  65.00   0.50    3.00    --  -11.60  45.00 178.17  286
;
_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      -0.0141325000
_diffrn_orient_matrix_UB_12      0.0022419000
_diffrn_orient_matrix_UB_13      0.0558655000
_diffrn_orient_matrix_UB_21      0.0705782000
_diffrn_orient_matrix_UB_22      0.0119670000
_diffrn_orient_matrix_UB_23      0.0411281000
_diffrn_orient_matrix_UB_31      -0.0188880000
_diffrn_orient_matrix_UB_32      0.0427048000
_diffrn_orient_matrix_UB_33      -0.0142587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3982
_reflns_number_total             4596
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.046
_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)+(0.0293P)²+0.8076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
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 0.99462(2) 0.38165(2) 0.78675(2) 0.03439(6) Uani 1 1 d . . . . .
O1 O 0.21180(11) 0.50217(7) 0.49244(11) 0.0275(2) Uani 1 1 d . . . . .
H1 H 0.127011 0.493500 0.454740 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.07833(12) 0.54182(8) 0.64991(12) 0.0347(3) Uani 1 1 d . . . . .
O3 O 0.29468(13) 0.54889(8) 0.81802(12) 0.0389(3) Uani 1 1 d . . . . .
N1 N 0.65327(12) 0.39458(7) 0.62343(12) 0.0220(2) Uani 1 1 d . . . . .
H1A H 0.696570 0.423759 0.589251 0.026 Uiso 1 1 calc R . . . .
C1 C 0.33822(15) 0.32251(9) 0.64773(16) 0.0256(3) Uani 1 1 d . . . . .
C2 C 0.47774(14) 0.34005(9) 0.65720(15) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.51109(15) 0.39323(9) 0.58022(15) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.446328 0.424115 0.508637 0.029 Uiso 1 1 calc R . . . .
C4 C 0.71470(14) 0.34149(8) 0.73041(13) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.85510(14) 0.32365(9) 0.81243(14) 0.0229(3) Uani 1 1 d . . . . .
C6 C 0.89006(16) 0.26578(10) 0.91280(15) 0.0296(3) Uani 1 1 d . . . . .
H6 H 0.983749 0.252834 0.967191 0.036 Uiso 1 1 calc R . . . .
C7 C 0.78455(17) 0.22631(10) 0.93313(16) 0.0314(3) Uani 1 1 d . . . . .
H7 H 0.809249 0.186114 0.999906 0.038 Uiso 1 1 calc R . . . .
C8 C 0.64480(16) 0.24547(9) 0.85668(15) 0.0269(3) Uani 1 1 d . . . . .
H8 H 0.576117 0.219772 0.873174 0.032 Uiso 1 1 calc R . . . .
C9 C 0.60802(14) 0.30433(8) 0.75368(14) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.30517(15) 0.23225(10) 0.65295(17) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.35555(18) 0.17254(10) 0.5947(2) 0.0391(4) Uani 1 1 d . . . . .
H11 H 0.409528 0.189463 0.553262 0.047 Uiso 1 1 calc R . . . .
C12 C 0.3261(2) 0.08837(12) 0.5978(2) 0.0527(6) Uani 1 1 d . . . . .
H12 H 0.360564 0.049070 0.558994 0.063 Uiso 1 1 calc R . . . .
C13 C 0.2460(2) 0.06307(13) 0.6580(2) 0.0586(7) Uani 1 1 d . . . . .
H13 H 0.225117 0.006624 0.658998 0.070 Uiso 1 1 calc R . . . .
C14 C 0.1964(2) 0.12090(13) 0.7171(2) 0.0554(6) Uani 1 1 d . . . . .
H14 H 0.142449 0.103281 0.758156 0.066 Uiso 1 1 calc R . . . .
C15 C 0.22645(18) 0.20584(12) 0.7158(2) 0.0401(4) Uani 1 1 d . . . . .
H15 H 0.193800 0.244587 0.757029 0.048 Uiso 1 1 calc R . . . .
C16 C 0.24539(15) 0.38221(9) 0.63542(16) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.160365 0.365394 0.631610 0.030 Uiso 1 1 calc R . . . .
C17 C 0.26820(14) 0.47436(9) 0.62728(15) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.369357 0.485332 0.671059 0.027 Uiso 1 1 calc R . . . .
C18 C 0.20102(15) 0.52508(9) 0.69769(15) 0.0237(3) Uani 1 1 d . . . . .
C19 C 0.2412(3) 0.60227(13) 0.8891(2) 0.0548(6) Uani 1 1 d . . . . .
H19A H 0.204399 0.652853 0.839183 0.082 Uiso 1 1 calc GR . . . .
H19B H 0.315761 0.615781 0.975357 0.082 Uiso 1 1 calc GR . . . .
H19C H 0.167992 0.573518 0.899657 0.082 Uiso 1 1 calc GR . . . .


_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 C5 1.8854(14) . ?
O1 C17 1.4236(18) . ?
O2 C18 1.2010(18) . ?
O3 C18 1.3220(19) . ?
O3 C19 1.450(2) . ?
N1 C3 1.3704(18) . ?
N1 C4 1.3707(18) . ?
C1 C2 1.4733(19) . ?
C1 C10 1.492(2) . ?
C1 C16 1.337(2) . ?
C2 C3 1.369(2) . ?
C2 C9 1.4396(19) . ?
C4 C5 1.3894(19) . ?
C4 C9 1.4109(19) . ?
C5 C6 1.372(2) . ?
C6 C7 1.398(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.402(2) . ?
C10 C11 1.395(3) . ?
C10 C15 1.387(2) . ?
C11 C12 1.385(3) . ?
C12 C13 1.371(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.396(3) . ?
C16 C17 1.501(2) . ?
C17 C18 1.520(2) . ?

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
C18 O3 C19 115.25(15) . . ?
C3 N1 C4 108.36(12) . . ?
C2 C1 C10 115.52(13) . . ?
C16 C1 C2 123.46(13) . . ?
C16 C1 C10 121.02(13) . . ?
C3 C2 C1 128.08(13) . . ?
C3 C2 C9 106.34(12) . . ?
C9 C2 C1 125.57(13) . . ?
C2 C3 N1 110.50(13) . . ?
N1 C4 C5 130.76(13) . . ?
N1 C4 C9 108.41(12) . . ?
C5 C4 C9 120.80(13) . . ?
C4 C5 Br1 119.32(11) . . ?
C6 C5 Br1 121.09(11) . . ?
C6 C5 C4 119.56(13) . . ?
C5 C6 C7 119.86(14) . . ?
C8 C7 C6 121.67(14) . . ?
C7 C8 C9 118.87(14) . . ?
C4 C9 C2 106.35(12) . . ?
C8 C9 C2 134.53(13) . . ?
C8 C9 C4 119.12(13) . . ?
C11 C10 C1 119.57(15) . . ?
C15 C10 C1 121.54(16) . . ?
C15 C10 C11 118.88(16) . . ?
C12 C11 C10 120.7(2) . . ?
C13 C12 C11 119.9(2) . . ?
C12 C13 C14 120.21(18) . . ?
C13 C14 C15 120.5(2) . . ?
C10 C15 C14 119.8(2) . . ?
C1 C16 C17 124.88(13) . . ?
O1 C17 C16 111.61(12) . . ?
O1 C17 C18 108.33(11) . . ?
C16 C17 C18 111.27(12) . . ?
O2 C18 O3 124.13(14) . . ?
O2 C18 C17 124.32(14) . . ?
O3 C18 C17 111.55(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 2.04 2.8598(15) 172.4 3_566 yes
N1 H1A O1 0.86 2.00 2.8622(16) 176.2 3_666 yes

_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.824
