# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_IKE13067
_database_code_depnum_ccdc_archive 'CCDC 1954370'
loop_
_audit_author_name
_audit_author_address
'Hideaki Ikeda'
;Osaka University
Japan
;
_audit_update_record             
;
2019-09-18 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H10 Br N O'
_chemical_formula_moiety         'C11 H10 Br N O'
_chemical_formula_weight         252.11
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.7320(7)
_cell_length_b                   7.2280(6)
_cell_length_c                   12.0162(17)
_cell_angle_alpha                80.831(11)
_cell_angle_beta                 86.517(11)
_cell_angle_gamma                62.902(8)
_cell_volume                     513.81(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2078
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252.00
_exptl_absorpt_coefficient_mu    3.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.173
_exptl_absorpt_correction_T_max  0.370

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            8391
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2353
_reflns_number_gt                2055
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0684
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.38194(4) 0.91523(4) 0.40487(2) 0.02652(9) Uani 1 1 d . . . . .
O1 O 1.0474(2) 0.7069(2) 0.17122(13) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.3469(3) 0.7886(3) -0.23197(17) 0.0252(4) Uani 1 1 d . . . . .
C1 C 1.1413(3) 0.8443(4) 0.39454(19) 0.0208(5) Uani 1 1 d . . . . .
H1 H 0.992804 0.964224 0.370469 0.025 Uiso 1 1 calc R U . . .
C2 C 1.1372(4) 0.6709(4) 0.47826(19) 0.0248(5) Uani 1 1 d . . . . .
H2A H 0.990038 0.685147 0.505928 0.030 Uiso 1 1 calc R U . . .
H2B H 1.260184 0.597627 0.534678 0.030 Uiso 1 1 calc R U . . .
C3 C 1.1921(4) 0.6396(4) 0.3571(2) 0.0235(5) Uani 1 1 d . . . . .
H3 H 1.351515 0.547720 0.340412 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0183(3) 0.6349(4) 0.28666(18) 0.0212(5) Uani 1 1 d . . . . .
H4A H 1.035014 0.490088 0.294390 0.025 Uiso 1 1 calc R U . . .
H4B H 0.867273 0.727159 0.311918 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8962(3) 0.7231(3) 0.09476(18) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.7159(3) 0.6789(3) 0.12198(18) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.691322 0.634734 0.198098 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5730(3) 0.7001(3) 0.03704(18) 0.0159(4) Uani 1 1 d . . . . .
H7 H 0.449203 0.671888 0.055334 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6099(3) 0.7623(3) -0.07488(18) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.7905(3) 0.8071(3) -0.10131(18) 0.0170(4) Uani 1 1 d . . . . .
H9 H 0.815797 0.850671 -0.177417 0.020 Uiso 1 1 calc R U . . .
C10 C 0.9315(3) 0.7880(3) -0.01702(18) 0.0161(4) Uani 1 1 d . . . . .
H10 H 1.053378 0.819264 -0.035182 0.019 Uiso 1 1 calc R U . . .
C11 C 0.4629(3) 0.7786(3) -0.16274(18) 0.0184(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.925(2) . ?
O1 C5 1.366(2) . ?
O1 C4 1.436(3) . ?
N1 C11 1.147(3) . ?
C1 C2 1.487(3) . ?
C1 C3 1.497(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.501(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.394(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(3) . ?
C8 C11 1.445(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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
C5 O1 C4 116.58(16) . . ?
C2 C1 C3 60.66(15) . . ?
C2 C1 BR1 117.87(15) . . ?
C3 C1 BR1 118.62(15) . . ?
C2 C1 H1 116.1 . . ?
C3 C1 H1 116.1 . . ?
BR1 C1 H1 116.1 . . ?
C1 C2 C3 60.01(16) . . ?
C1 C2 H2A 117.8 . . ?
C3 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
C3 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
C1 C3 C4 117.29(19) . . ?
C1 C3 C2 59.33(15) . . ?
C4 C3 C2 117.54(19) . . ?
C1 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C2 C3 H3 116.8 . . ?
O1 C4 C3 108.20(18) . . ?
O1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
O1 C5 C10 115.45(18) . . ?
O1 C5 C6 124.52(19) . . ?
C10 C5 C6 120.04(18) . . ?
C7 C6 C5 119.54(19) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.45(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.61(18) . . ?
C7 C8 C11 119.82(19) . . ?
C9 C8 C11 120.57(19) . . ?
C10 C9 C8 120.06(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 120.29(19) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
N1 C11 C8 179.0(2) . . ?

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 C1 C2 C3 -108.92(18) . . . . ?
C2 C1 C3 C4 107.4(2) . . . . ?
BR1 C1 C3 C4 -144.90(17) . . . . ?
BR1 C1 C3 C2 107.71(18) . . . . ?
C1 C2 C3 C4 -107.0(2) . . . . ?
C5 O1 C4 C3 -176.94(17) . . . . ?
C1 C3 C4 O1 84.2(2) . . . . ?
C2 C3 C4 O1 152.00(19) . . . . ?
C4 O1 C5 C10 -178.40(18) . . . . ?
C4 O1 C5 C6 1.4(3) . . . . ?
O1 C5 C6 C7 -179.74(18) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C11 178.47(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C11 C8 C9 C10 -179.04(19) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
O1 C5 C10 C9 179.18(18) . . . . ?
C6 C5 C10 C9 -0.6(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


