# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_m-4BB
_database_code_depnum_ccdc_archive 'CCDC 2266604'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   6.1745(3)
_cell_length_b                   6.8716(3)
_cell_length_c                   28.3078(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.189(4)
_cell_angle_gamma                90
_cell_volume                     1194.06(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6122
_cell_measurement_theta_min      2.8650
_cell_measurement_theta_max      30.6890

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.769
_shelx_estimated_absorpt_T_min   0.345
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_T_min  0.47130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            7816
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.895
_diffrn_reflns_theta_max         30.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1708
_reflns_number_gt                1584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.3213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1708
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.381
_refine_ls_restrained_S_all      1.381
_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_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
O1 O 0.3702(9) 0.1676(9) 0.0261(2) 0.0166(12) Uani 0.5 1 d . . P A 1
H1 H 0.439196 0.181377 0.002304 0.025 Uiso 0.5 1 calc R U P A 1
C1 C 0.5058(6) 0.2001(6) 0.06628(13) 0.0138(7) Uani 1 1 d . . . . .
H2 H 0.417872 0.167597 0.037752 0.017 Uiso 0.5 1 calc R U P A 2
C2 C 0.4251(6) 0.1714(5) 0.10990(13) 0.0117(7) Uani 1 1 d . . . . .
H3 H 0.285937 0.114509 0.111593 0.014 Uiso 1 1 calc R U . . .
C3 C 0.5548(6) 0.2287(5) 0.15104(13) 0.0114(7) Uani 1 1 d . . . . .
C4 C 0.7624(6) 0.3048(6) 0.15032(13) 0.0140(7) Uani 1 1 d . . . . .
H4 H 0.848013 0.339626 0.178981 0.017 Uiso 1 1 calc R U . . .
C5 C 0.8426(6) 0.3291(6) 0.10628(13) 0.0119(7) Uani 1 1 d . . . . .
H5 H 0.984119 0.381614 0.104982 0.014 Uiso 1 1 calc R U . . .
C6 C 0.7158(6) 0.2764(6) 0.06397(13) 0.0118(7) Uani 1 1 d . . . . .
Br1 Br 0.44011(7) 0.19346(7) 0.21014(2) 0.01940(13) Uani 1 1 d . . . . .
C7 C 0.807(2) 0.306(7) 0.0192(5) 0.010(4) Uani 0.5 1 d . . P B -1
H6 H 0.952565 0.350821 0.019107 0.012 Uiso 0.5 1 calc R U P B -1
N1 N 0.6884(19) 0.272(6) -0.0204(4) 0.010(4) Uani 0.5 1 d . . P B -1


_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
O1 C1 1.356(6) . ?
O1 H1 0.8400 . ?
C1 C2 1.395(5) . ?
C1 C6 1.407(5) . ?
C1 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C2 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C3 Br1 1.901(4) . ?
C4 C5 1.400(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(13) . ?
C7 N1 1.293(19) . ?
C7 H6 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 118.2(4) . . ?
O1 C1 C6 120.7(4) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H2 119.6 . . ?
C6 C1 H2 119.6 . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H3 121.0 . . ?
C3 C2 H3 121.0 . . ?
C4 C3 C2 122.8(3) . . ?
C4 C3 Br1 119.6(3) . . ?
C2 C3 Br1 117.6(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 118.3(12) . . ?
C1 C6 C7 122.6(12) . . ?
N1 C7 C6 120(2) . . ?
N1 C7 H6 120.2 . . ?
C6 C7 H6 120.2 . . ?

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
O1 C1 C2 C3 -171.9(5) . . . . ?
C6 C1 C2 C3 2.8(6) . . . . ?
C1 C2 C3 C4 -2.7(6) . . . . ?
C1 C2 C3 Br1 178.8(3) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
Br1 C3 C4 C5 180.0(3) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 179.5(18) . . . . ?
O1 C1 C6 C5 172.8(5) . . . . ?
C2 C1 C6 C5 -1.7(6) . . . . ?
O1 C1 C6 C7 -6(2) . . . . ?
C2 C1 C6 C7 179.3(19) . . . . ?
C5 C6 C7 N1 -175(4) . . . . ?
C1 C6 C7 N1 4(6) . . . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.134


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexane'
####################################################################### 
# 
# 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_o1-4BB
_database_code_depnum_ccdc_archive 'CCDC 2266605'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   6.05690(10)
_cell_length_b                   6.93300(10)
_cell_length_c                   28.5038(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1196.95(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10439
_cell_measurement_theta_min      4.6480
_cell_measurement_theta_max      70.7840

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_shelx_estimated_absorpt_T_min   0.209
_shelx_estimated_absorpt_T_max   0.312
_exptl_absorpt_coefficient_mu    8.437
_exptl_absorpt_correction_T_min  0.183
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10509
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         71.133
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             2120
_reflns_number_gt                2119
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.827
_reflns_Friedel_fraction_full    0.844

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+1.1923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2120
_refine_ls_number_parameters     155
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.157
_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_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
O1 O -0.3953(6) 0.8349(6) -0.09403(15) 0.0188(8) Uani 1 1 d . . . . .
H1 H -0.314661 0.818639 -0.070387 0.028 Uiso 1 1 calc R U . . .
C1 C -0.2808(11) 0.7926(6) -0.1329(3) 0.0144(12) Uani 1 1 d . . . . .
C2 C -0.3761(9) 0.8215(8) -0.1765(3) 0.0164(11) Uani 1 1 d . . . . .
H2 H -0.518830 0.877573 -0.178603 0.020 Uiso 1 1 calc R U . . .
C3 C -0.2681(11) 0.7708(7) -0.2161(3) 0.0178(12) Uani 1 1 d . . . . .
C4 C -0.0508(11) 0.6949(7) -0.2161(3) 0.0153(14) Uani 1 1 d . . . . .
H3 H 0.022572 0.662115 -0.244495 0.018 Uiso 1 1 calc R U . . .
C5 C 0.0489(10) 0.6710(8) -0.1731(2) 0.0147(11) Uani 1 1 d . . . . .
H4 H 0.195665 0.623042 -0.171531 0.018 Uiso 1 1 calc R U . . .
C6 C -0.0656(10) 0.7175(7) -0.1312(3) 0.0126(13) Uani 1 1 d . . . . .
Br1 Br -0.41333(9) 0.80070(8) -0.27483(2) 0.0218(2) Uani 1 1 d . . . . .
C7 C 0.0498(12) 0.6961(7) -0.0861(3) 0.0165(13) Uani 1 1 d . . . . .
H5 H 0.201146 0.660258 -0.085688 0.020 Uiso 1 1 calc R U . . .
N1 N -0.0530(9) 0.7257(7) -0.0470(3) 0.0143(10) Uani 1 1 d . . . . .
C8 C 0.0623(11) 0.7329(10) -0.0042(3) 0.0166(12) Uani 1 1 d . . . . .
C9 C 0.2738(11) 0.8133(7) -0.0004(3) 0.0178(13) Uani 1 1 d . . . . .
H6 H 0.347156 0.856672 -0.027951 0.021 Uiso 1 1 calc R U . . .
C10 C 0.3786(10) 0.8311(8) 0.0428(2) 0.0162(11) Uani 1 1 d . . . . .
H7 H 0.521703 0.886411 0.045061 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2685(10) 0.7656(8) 0.0830(2) 0.0154(11) Uani 1 1 d . . . . .
C12 C 0.0585(11) 0.6873(8) 0.0798(3) 0.0177(14) Uani 1 1 d . . . . .
H8 H -0.016053 0.644810 0.107189 0.021 Uiso 1 1 calc R U . . .
C13 C -0.0415(10) 0.6716(8) 0.0364(2) 0.0149(11) Uani 1 1 d . . . . .
H9 H -0.185192 0.617348 0.034351 0.018 Uiso 1 1 calc R U . . .
Br2 Br 0.41586(10) 0.78736(8) 0.14116(2) 0.0225(2) Uani 1 1 d . . . . .


_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
O1 C1 1.341(8) . ?
O1 H1 0.8400 . ?
C1 C2 1.384(10) . ?
C1 C6 1.405(9) . ?
C2 C3 1.351(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.418(9) . ?
C3 Br1 1.902(7) . ?
C4 C5 1.376(10) . ?
C4 H3 0.9500 . ?
C5 C6 1.420(10) . ?
C5 H4 0.9500 . ?
C6 C7 1.470(10) . ?
C7 N1 1.293(7) . ?
C7 H5 0.9500 . ?
N1 C8 1.405(9) . ?
C8 C13 1.384(11) . ?
C8 C9 1.401(10) . ?
C9 C10 1.393(11) . ?
C9 H6 0.9500 . ?
C10 C11 1.400(8) . ?
C10 H7 0.9500 . ?
C11 C12 1.386(9) . ?
C11 Br2 1.890(7) . ?
C12 C13 1.381(10) . ?
C12 H8 0.9500 . ?
C13 H9 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.7(6) . . ?
O1 C1 C6 122.1(6) . . ?
C2 C1 C6 118.2(7) . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 123.1(7) . . ?
C2 C3 Br1 118.9(5) . . ?
C4 C3 Br1 118.0(6) . . ?
C5 C4 C3 116.8(7) . . ?
C5 C4 H3 121.6 . . ?
C3 C4 H3 121.6 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H4 119.7 . . ?
C6 C5 H4 119.7 . . ?
C1 C6 C5 120.5(7) . . ?
C1 C6 C7 120.7(6) . . ?
C5 C6 C7 118.8(6) . . ?
N1 C7 C6 120.6(5) . . ?
N1 C7 H5 119.7 . . ?
C6 C7 H5 119.7 . . ?
C7 N1 C8 120.9(5) . . ?
C13 C8 C9 118.2(7) . . ?
C13 C8 N1 119.2(6) . . ?
C9 C8 N1 122.4(7) . . ?
C10 C9 C8 121.3(7) . . ?
C10 C9 H6 119.3 . . ?
C8 C9 H6 119.3 . . ?
C9 C10 C11 118.5(6) . . ?
C9 C10 H7 120.7 . . ?
C11 C10 H7 120.7 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 Br2 121.5(5) . . ?
C10 C11 Br2 117.8(5) . . ?
C13 C12 C11 119.5(7) . . ?
C13 C12 H8 120.3 . . ?
C11 C12 H8 120.3 . . ?
C12 C13 C8 121.7(6) . . ?
C12 C13 H9 119.2 . . ?
C8 C13 H9 119.2 . . ?

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
O1 C1 C2 C3 -176.6(5) . . . . ?
C6 C1 C2 C3 2.8(7) . . . . ?
C1 C2 C3 C4 -3.1(8) . . . . ?
C1 C2 C3 Br1 176.6(4) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
Br1 C3 C4 C5 -178.7(4) . . . . ?
C3 C4 C5 C6 1.3(8) . . . . ?
O1 C1 C6 C5 178.8(5) . . . . ?
C2 C1 C6 C5 -0.6(7) . . . . ?
O1 C1 C6 C7 -4.8(8) . . . . ?
C2 C1 C6 C7 175.8(5) . . . . ?
C4 C5 C6 C1 -1.4(9) . . . . ?
C4 C5 C6 C7 -177.9(5) . . . . ?
C1 C6 C7 N1 7.7(8) . . . . ?
C5 C6 C7 N1 -175.8(5) . . . . ?
C6 C7 N1 C8 -170.8(5) . . . . ?
C7 N1 C8 C13 -148.7(6) . . . . ?
C7 N1 C8 C9 36.1(9) . . . . ?
C13 C8 C9 C10 0.3(9) . . . . ?
N1 C8 C9 C10 175.5(5) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C9 C10 C11 Br2 179.0(4) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
Br2 C11 C12 C13 -179.0(4) . . . . ?
C11 C12 C13 C8 -0.3(9) . . . . ?
C9 C8 C13 C12 -0.3(10) . . . . ?
N1 C8 C13 C12 -175.7(5) . . . . ?

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 N1 0.84 1.84 2.583(7) 147.2 . yes
C9 H6 O1 0.95 2.45 3.340(9) 155.9 1_655 yes

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.150


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
####################################################################### 
# 
# 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_o2-4BB
_database_code_depnum_ccdc_archive 'CCDC 2266606'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   56.5791(10)
_cell_length_b                   6.89400(10)
_cell_length_c                   6.10180(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2380.05(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    15935
_cell_measurement_theta_min      3.2050
_cell_measurement_theta_max      70.7670

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    8.488
_shelx_estimated_absorpt_T_min   0.310
_shelx_estimated_absorpt_T_max   0.728
_exptl_absorpt_correction_T_min  0.38770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            21429
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_h_max       69
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.124
_diffrn_reflns_theta_max         71.221
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2304
_reflns_number_gt                2295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0070P)²+30.5699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2304
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.375
_refine_ls_restrained_S_all      1.375
_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_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
O1 O 0.11114(8) 0.4172(7) 0.7734(8) 0.0231(10) Uani 1 1 d . . . . .
H1 H 0.123049 0.438970 0.695054 0.035 Uiso 1 1 calc R U . . .
C1 C 0.09133(11) 0.4600(9) 0.6594(10) 0.0161(13) Uani 1 1 d . . . . .
C2 C 0.06966(10) 0.4249(9) 0.7582(10) 0.0160(12) Uani 1 1 d . . . . .
H2 H 0.068877 0.366608 0.899062 0.019 Uiso 1 1 calc R U . . .
C3 C 0.04920(10) 0.4762(9) 0.6481(10) 0.0152(13) Uani 1 1 d . . . . .
C4 C 0.04957(11) 0.5524(8) 0.4363(11) 0.0163(13) Uani 1 1 d . . . . .
H3 H 0.035316 0.585120 0.362766 0.020 Uiso 1 1 calc R U . . .
C5 C 0.07118(11) 0.5789(9) 0.3369(10) 0.0149(12) Uani 1 1 d . . . . .
H4 H 0.071769 0.628229 0.191609 0.018 Uiso 1 1 calc R U . . .
C6 C 0.09243(10) 0.5346(8) 0.4460(11) 0.0146(12) Uani 1 1 d . . . . .
Br1 Br 0.01986(2) 0.43787(10) 0.79128(12) 0.0218(2) Uani 1 1 d . . . . .
C7 C 0.11483(11) 0.5545(8) 0.3330(10) 0.0137(12) Uani 1 1 d . . . . .
H5 H 0.114890 0.589817 0.182537 0.016 Uiso 1 1 calc R U . . .
N1 N 0.13450(9) 0.5257(7) 0.4304(9) 0.0156(11) Uani 1 1 d . . . . .
C8 C 0.15616(10) 0.5191(9) 0.3164(10) 0.0143(12) Uani 1 1 d . . . . .
C9 C 0.15759(11) 0.4384(9) 0.1061(11) 0.0167(13) Uani 1 1 d . . . . .
H6 H 0.143684 0.394549 0.034367 0.020 Uiso 1 1 calc R U . . .
C10 C 0.17946(11) 0.4224(9) 0.0024(10) 0.0161(13) Uani 1 1 d . . . . .
H7 H 0.180540 0.369714 -0.141117 0.019 Uiso 1 1 calc R U . . .
C11 C 0.19952(11) 0.4840(9) 0.1107(11) 0.0166(13) Uani 1 1 d . . . . .
C12 C 0.19847(11) 0.5608(9) 0.3198(11) 0.0183(13) Uani 1 1 d . . . . .
H8 H 0.212471 0.601825 0.392225 0.022 Uiso 1 1 calc R U . . .
C13 C 0.17678(11) 0.5770(9) 0.4217(11) 0.0176(13) Uani 1 1 d . . . . .
H9 H 0.175927 0.628506 0.565929 0.021 Uiso 1 1 calc R U . . .
Br2 Br 0.22904(2) 0.46091(10) -0.03526(13) 0.0237(2) Uani 1 1 d . . . . .


_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
O1 C1 1.351(7) . ?
O1 H1 0.8400 . ?
C1 C2 1.387(9) . ?
C1 C6 1.402(9) . ?
C2 C3 1.384(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(9) . ?
C3 Br1 1.894(6) . ?
C4 C5 1.377(9) . ?
C4 H3 0.9500 . ?
C5 C6 1.408(8) . ?
C5 H4 0.9500 . ?
C6 C7 1.449(8) . ?
C7 N1 1.277(8) . ?
C7 H5 0.9500 . ?
N1 C8 1.410(8) . ?
C8 C13 1.390(9) . ?
C8 C9 1.401(9) . ?
C9 C10 1.394(9) . ?
C9 H6 0.9500 . ?
C10 C11 1.380(9) . ?
C10 H7 0.9500 . ?
C11 C12 1.383(9) . ?
C11 Br2 1.900(6) . ?
C12 C13 1.380(9) . ?
C12 H8 0.9500 . ?
C13 H9 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 118.1(6) . . ?
O1 C1 C6 121.4(6) . . ?
C2 C1 C6 120.4(6) . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 122.2(6) . . ?
C2 C3 Br1 118.2(5) . . ?
C4 C3 Br1 119.5(5) . . ?
C5 C4 C3 118.1(6) . . ?
C5 C4 H3 120.9 . . ?
C3 C4 H3 120.9 . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 H4 119.3 . . ?
C6 C5 H4 119.3 . . ?
C1 C6 C5 118.8(6) . . ?
C1 C6 C7 121.0(6) . . ?
C5 C6 C7 120.1(6) . . ?
N1 C7 C6 121.7(6) . . ?
N1 C7 H5 119.1 . . ?
C6 C7 H5 119.1 . . ?
C7 N1 C8 122.2(5) . . ?
C13 C8 C9 119.3(6) . . ?
C13 C8 N1 119.5(6) . . ?
C9 C8 N1 121.0(5) . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H6 120.0 . . ?
C8 C9 H6 120.0 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H7 120.4 . . ?
C9 C10 H7 120.4 . . ?
C10 C11 C12 121.6(6) . . ?
C10 C11 Br2 118.2(5) . . ?
C12 C11 Br2 120.2(5) . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 H8 120.5 . . ?
C11 C12 H8 120.5 . . ?
C12 C13 C8 121.0(6) . . ?
C12 C13 H9 119.5 . . ?
C8 C13 H9 119.5 . . ?

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
O1 C1 C2 C3 177.0(6) . . . . ?
C6 C1 C2 C3 -4.1(9) . . . . ?
C1 C2 C3 C4 3.5(9) . . . . ?
C1 C2 C3 Br1 -177.2(5) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
Br1 C3 C4 C5 179.8(5) . . . . ?
C3 C4 C5 C6 -1.3(9) . . . . ?
O1 C1 C6 C5 -179.1(6) . . . . ?
C2 C1 C6 C5 2.0(9) . . . . ?
O1 C1 C6 C7 4.9(9) . . . . ?
C2 C1 C6 C7 -174.0(6) . . . . ?
C4 C5 C6 C1 0.7(9) . . . . ?
C4 C5 C6 C7 176.8(6) . . . . ?
C1 C6 C7 N1 -7.9(9) . . . . ?
C5 C6 C7 N1 176.1(6) . . . . ?
C6 C7 N1 C8 171.4(5) . . . . ?
C7 N1 C8 C13 150.2(6) . . . . ?
C7 N1 C8 C9 -35.8(9) . . . . ?
C13 C8 C9 C10 -2.0(9) . . . . ?
N1 C8 C9 C10 -175.9(6) . . . . ?
C8 C9 C10 C11 1.0(9) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C9 C10 C11 Br2 -179.9(5) . . . . ?
C10 C11 C12 C13 -0.4(9) . . . . ?
Br2 C11 C12 C13 179.6(5) . . . . ?
C11 C12 C13 C8 -0.6(9) . . . . ?
C9 C8 C13 C12 1.8(9) . . . . ?
N1 C8 C13 C12 175.8(6) . . . . ?

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 N1 0.84 1.84 2.586(7) 147.2 . yes
C9 H6 O1 0.95 2.44 3.324(8) 155.0 1_554 yes

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.160


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane amd hexane'
####################################################################### 
# 
# 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_4CB
_database_code_depnum_ccdc_archive 'CCDC 2266609'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-05-31 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br Cl N O'
_chemical_formula_sum            'C13 H9 Br Cl N O'
_chemical_formula_weight         310.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   55.8702(10)
_cell_length_b                   6.9161(2)
_cell_length_c                   6.10830(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2360.27(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    10371
_cell_measurement_theta_min      3.1700
_cell_measurement_theta_max      73.1970

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.674
_shelx_estimated_absorpt_T_min   0.617
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_T_min  0.75302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            32779
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_limit_h_min       -69
_diffrn_reflns_limit_h_max       69
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.164
_diffrn_reflns_theta_max         74.271
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2405
_reflns_number_gt                2139
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+99.3479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2405
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1145
_refine_ls_wR_factor_ref         0.2599
_refine_ls_wR_factor_gt          0.2580
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.171
_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_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
O1 O 0.10893(14) 0.5809(15) 0.7957(15) 0.038(2) Uani 1 1 d . . . . .
H1 H 0.120(3) 0.58(2) 0.74(3) 0.057 Uiso 1 1 d . U . . .
C1 C 0.0891(2) 0.5389(16) 0.677(2) 0.032(3) Uani 1 1 d . . . . .
C2 C 0.0669(2) 0.5750(18) 0.7825(18) 0.032(3) Uani 1 1 d . . . . .
H2 H 0.065992 0.628477 0.925510 0.038 Uiso 1 1 calc R U . . .
C3 C 0.0463(2) 0.5263(18) 0.661(2) 0.033(3) Uani 1 1 d . . . . .
C4 C 0.0469(2) 0.4485(17) 0.4565(19) 0.032(3) Uani 1 1 d . . . . .
H3 H 0.032507 0.413974 0.382973 0.039 Uiso 1 1 calc R U . . .
C5 C 0.0689(2) 0.4211(17) 0.359(2) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.069353 0.370473 0.214505 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0903(2) 0.4637(15) 0.4612(16) 0.026(2) Uani 1 1 d . . . . .
Cl1 Cl 0.01906(5) 0.5645(5) 0.7959(6) 0.0460(8) Uani 1 1 d . . . . .
C7 C 0.1130(2) 0.4447(16) 0.356(2) 0.033(3) Uani 1 1 d . . . . .
H5 H 0.113409 0.408958 0.205763 0.039 Uiso 1 1 calc R U . . .
N1 N 0.13288(16) 0.4739(14) 0.4560(15) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.1548(2) 0.4812(17) 0.336(2) 0.031(3) Uani 1 1 d . . . . .
C9 C 0.1756(2) 0.4227(17) 0.4445(18) 0.029(2) Uani 1 1 d . . . . .
H6 H 0.174519 0.371999 0.588789 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1976(2) 0.4380(18) 0.344(2) 0.036(3) Uani 1 1 d . . . . .
H7 H 0.211697 0.393669 0.414676 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1987(2) 0.5203(16) 0.1347(19) 0.030(2) Uani 1 1 d . . . . .
C12 C 0.1784(2) 0.5764(18) 0.030(2) 0.036(3) Uani 1 1 d . . . . .
H8 H 0.179482 0.628572 -0.113089 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1563(2) 0.5595(16) 0.1274(19) 0.029(2) Uani 1 1 d . . . . .
H9 H 0.142340 0.600960 0.052724 0.035 Uiso 1 1 calc R U . . .
Br1 Br 0.22866(2) 0.5384(2) -0.0121(3) 0.0448(4) Uani 1 1 d . . . . .


_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
O1 C1 1.358(14) . ?
O1 H1 0.70(15) . ?
C1 C2 1.417(16) . ?
C1 C6 1.419(16) . ?
C2 C3 1.408(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(17) . ?
C3 Cl1 1.751(11) . ?
C4 C5 1.380(16) . ?
C4 H3 0.9500 . ?
C5 C6 1.380(16) . ?
C5 H4 0.9500 . ?
C6 C7 1.428(16) . ?
C7 N1 1.284(15) . ?
C7 H5 0.9500 . ?
N1 C8 1.428(14) . ?
C8 C13 1.387(16) . ?
C8 C9 1.396(16) . ?
C9 C10 1.380(16) . ?
C9 H6 0.9500 . ?
C10 C11 1.399(17) . ?
C10 H7 0.9500 . ?
C11 C12 1.356(16) . ?
C11 Br1 1.905(11) . ?
C12 C13 1.371(16) . ?
C12 H8 0.9500 . ?
C13 H9 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
C1 O1 H1 119(10) . . ?
O1 C1 C2 115.7(11) . . ?
O1 C1 C6 122.3(10) . . ?
C2 C1 C6 122.0(11) . . ?
C3 C2 C1 115.6(11) . . ?
C3 C2 H2 122.2 . . ?
C1 C2 H2 122.2 . . ?
C4 C3 C2 124.0(11) . . ?
C4 C3 Cl1 120.7(9) . . ?
C2 C3 Cl1 115.3(9) . . ?
C3 C4 C5 118.0(11) . . ?
C3 C4 H3 121.0 . . ?
C5 C4 H3 121.0 . . ?
C4 C5 C6 123.2(12) . . ?
C4 C5 H4 118.4 . . ?
C6 C5 H4 118.4 . . ?
C5 C6 C1 117.1(11) . . ?
C5 C6 C7 123.1(11) . . ?
C1 C6 C7 119.7(10) . . ?
N1 C7 C6 122.7(12) . . ?
N1 C7 H5 118.7 . . ?
C6 C7 H5 118.7 . . ?
C7 N1 C8 120.2(10) . . ?
C13 C8 C9 119.9(11) . . ?
C13 C8 N1 122.6(10) . . ?
C9 C8 N1 117.3(11) . . ?
C10 C9 C8 120.4(11) . . ?
C10 C9 H6 119.8 . . ?
C8 C9 H6 119.8 . . ?
C9 C10 C11 118.4(11) . . ?
C9 C10 H7 120.8 . . ?
C11 C10 H7 120.8 . . ?
C12 C11 C10 120.6(11) . . ?
C12 C11 Br1 119.7(10) . . ?
C10 C11 Br1 119.6(9) . . ?
C11 C12 C13 121.5(12) . . ?
C11 C12 H8 119.2 . . ?
C13 C12 H8 119.2 . . ?
C12 C13 C8 119.1(11) . . ?
C12 C13 H9 120.5 . . ?
C8 C13 H9 120.5 . . ?

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
O1 C1 C2 C3 -178.3(11) . . . . ?
C6 C1 C2 C3 1.7(17) . . . . ?
C1 C2 C3 C4 0.4(18) . . . . ?
C1 C2 C3 Cl1 178.1(9) . . . . ?
C2 C3 C4 C5 -2.1(19) . . . . ?
Cl1 C3 C4 C5 -179.8(9) . . . . ?
C3 C4 C5 C6 1.9(18) . . . . ?
C4 C5 C6 C1 0.1(17) . . . . ?
C4 C5 C6 C7 -176.7(11) . . . . ?
O1 C1 C6 C5 178.1(11) . . . . ?
C2 C1 C6 C5 -1.9(16) . . . . ?
O1 C1 C6 C7 -5.0(16) . . . . ?
C2 C1 C6 C7 174.9(11) . . . . ?
C5 C6 C7 N1 -175.9(11) . . . . ?
C1 C6 C7 N1 7.4(17) . . . . ?
C6 C7 N1 C8 -170.7(10) . . . . ?
C7 N1 C8 C13 35.5(16) . . . . ?
C7 N1 C8 C9 -150.5(11) . . . . ?
C13 C8 C9 C10 -1.6(17) . . . . ?
N1 C8 C9 C10 -175.7(11) . . . . ?
C8 C9 C10 C11 2.5(17) . . . . ?
C9 C10 C11 C12 -2.6(17) . . . . ?
C9 C10 C11 Br1 -178.6(9) . . . . ?
C10 C11 C12 C13 1.8(18) . . . . ?
Br1 C11 C12 C13 177.7(9) . . . . ?
C11 C12 C13 C8 -0.8(17) . . . . ?
C9 C8 C13 C12 0.6(16) . . . . ?
N1 C8 C13 C12 174.4(11) . . . . ?

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 N1 0.70(15) 2.04(16) 2.577(13) 134(17) . yes
C13 H9 O1 0.95 2.44 3.338(14) 157.0 1_554 yes

_refine_diff_density_max         2.448
_refine_diff_density_min         -1.509
_refine_diff_density_rms         0.196


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane amd hexane'
####################################################################### 
# 
# 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_4BC
_database_code_depnum_ccdc_archive 'CCDC 2266607'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br Cl N O'
_chemical_formula_sum            'C13 H9 Br Cl N O'
_chemical_formula_weight         310.57

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   27.8584(9)
_cell_length_b                   6.8627(3)
_cell_length_c                   6.1547(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.840(3)
_cell_angle_gamma                90
_cell_volume                     1170.57(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    6021
_cell_measurement_theta_min      2.2480
_cell_measurement_theta_max      27.2860

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.720
_shelx_estimated_absorpt_T_min   0.433
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_T_min  0.60841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            14008
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         27.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2521
_reflns_number_gt                2208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.0789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2521
_refine_ls_number_parameters     177
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.135
_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_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
C1 C 0.18598(19) 0.4592(8) 0.7447(9) 0.0170(10) Uani 1 1 d D . . . .
H12 H 0.214953 0.430538 0.834119 0.020 Uiso 0.095(4) 1 calc R U P A 2
C2 C 0.1416(2) 0.4278(8) 0.8234(9) 0.0183(10) Uani 1 1 d . . . . .
H1 H 0.140043 0.373760 0.964618 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0999(2) 0.4758(8) 0.6947(9) 0.0180(11) Uani 1 1 d . . . . .
C4 C 0.1004(2) 0.5508(8) 0.4846(9) 0.0188(11) Uani 1 1 d . . . . .
H2 H 0.071143 0.582037 0.398289 0.023 Uiso 1 1 calc R U . . .
C5 C 0.14427(19) 0.5785(8) 0.4057(9) 0.0184(11) Uani 1 1 d D . . . .
H3 H 0.145151 0.629167 0.262547 0.022 Uiso 1 1 calc R U . . .
C6 C 0.18806(19) 0.5338(8) 0.5314(8) 0.0168(10) Uani 1 1 d D . . . .
C7 C 0.3181(2) 0.5193(8) 0.4607(9) 0.0189(11) Uani 1 1 d D . . . .
C8 C 0.3603(2) 0.5776(9) 0.5868(9) 0.0206(11) Uani 1 1 d D . . . .
H4 H 0.358644 0.629027 0.729094 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4048(2) 0.5604(9) 0.5038(9) 0.0230(12) Uani 1 1 d . . . . .
H5 H 0.433356 0.603800 0.587037 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4070(2) 0.4796(9) 0.2992(9) 0.0206(12) Uani 1 1 d . . . . .
C11 C 0.3654(2) 0.4192(8) 0.1727(9) 0.0210(11) Uani 1 1 d D . . . .
H6 H 0.367415 0.365371 0.031614 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3211(2) 0.4382(9) 0.2546(9) 0.0213(11) Uani 1 1 d D . . . .
H13 H 0.292649 0.395804 0.169889 0.026 Uiso 0.905(4) 1 calc R U P A 1
O1 O 0.22702(15) 0.4199(7) 0.8760(6) 0.0207(9) Uani 0.905(4) 1 d . . P A 1
H7 H 0.251088 0.451629 0.812062 0.031 Uiso 0.905(4) 1 calc R U P A 1
Br1 Br 0.04018(3) 0.43753(13) 0.81104(14) 0.0207(2) Uani 0.905(4) 1 d . . P A 1
C13 C 0.2337(3) 0.553(6) 0.439(3) 0.0202(17) Uani 0.905(4) 1 d D . P A 1
H8 H 0.233747 0.583385 0.288500 0.024 Uiso 0.905(4) 1 calc R U P A 1
N1 N 0.27402(19) 0.5290(13) 0.5569(10) 0.0168(13) Uani 0.905(4) 1 d . . P A 1
Cl1 Cl 0.4625(3) 0.4589(9) 0.1974(12) 0.0308(9) Uani 0.905(4) 1 d . . P A 1
O2 O 0.2777(9) 0.416(10) 0.123(6) 0.051(16) Uani 0.095(4) 1 d D . P A 2
H11 H 0.254551 0.434359 0.197258 0.076 Uiso 0.095(4) 1 calc R U P A 2
Br2 Br 0.4611(12) 0.425(4) 0.171(5) 0.0308(9) Uani 0.095(4) 1 d . . P A 2
C14 C 0.2735(9) 0.507(16) 0.561(8) 0.0168(13) Uani 0.095(4) 1 d D . P A 2
H10 H 0.273195 0.462237 0.707343 0.020 Uiso 0.095(4) 1 calc R U P A 2
N2 N 0.2330(15) 0.56(5) 0.44(3) 0.0202(17) Uani 0.095(4) 1 d D . P A 2
Cl2 Cl 0.0553(8) 0.441(4) 0.813(4) 0.0207(2) Uani 0.095(4) 1 d . . P A 2


_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
C1 O1 1.358(6) . ?
C1 C2 1.390(8) . ?
C1 C6 1.416(7) . ?
C1 H12 0.9500 . ?
C2 C3 1.378(8) . ?
C2 H1 0.9500 . ?
C3 C4 1.393(8) . ?
C3 Cl2 1.52(2) . ?
C3 Br1 1.896(5) . ?
C4 C5 1.374(8) . ?
C4 H2 0.9500 . ?
C5 C6 1.410(7) . ?
C5 H3 0.9500 . ?
C6 N2 1.422(17) . ?
C6 C13 1.450(8) . ?
C7 C12 1.395(8) . ?
C7 C8 1.401(8) . ?
C7 N1 1.418(8) . ?
C7 C14 1.45(3) . ?
C8 C9 1.391(8) . ?
C8 H4 0.9500 . ?
C9 C10 1.383(8) . ?
C9 H5 0.9500 . ?
C10 C11 1.391(8) . ?
C10 Cl1 1.733(9) . ?
C10 Br2 1.81(3) . ?
C11 C12 1.386(8) . ?
C11 H6 0.9500 . ?
C12 O2 1.395(17) . ?
C12 H13 0.9500 . ?
O1 H7 0.8400 . ?
C13 N1 1.285(11) . ?
C13 H8 0.9500 . ?
O2 H11 0.8400 . ?
C14 N2 1.32(2) . ?
C14 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
O1 C1 C2 119.1(5) . . ?
O1 C1 C6 120.8(5) . . ?
C2 C1 C6 120.1(5) . . ?
C2 C1 H12 120.0 . . ?
C6 C1 H12 120.0 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H1 120.3 . . ?
C1 C2 H1 120.3 . . ?
C2 C3 C4 122.4(5) . . ?
C2 C3 Cl2 111.7(10) . . ?
C4 C3 Cl2 125.9(11) . . ?
C2 C3 Br1 118.1(4) . . ?
C4 C3 Br1 119.5(4) . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 H2 120.9 . . ?
C3 C4 H2 120.9 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 H3 119.1 . . ?
C6 C5 H3 119.1 . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 N2 121(2) . . ?
C1 C6 N2 120.9(19) . . ?
C5 C6 C13 120.6(6) . . ?
C1 C6 C13 121.1(5) . . ?
C12 C7 C8 119.5(5) . . ?
C12 C7 N1 122.3(5) . . ?
C8 C7 N1 118.0(5) . . ?
C12 C7 C14 120(3) . . ?
C8 C7 C14 119(2) . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H4 120.0 . . ?
C7 C8 H4 120.0 . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H5 120.3 . . ?
C8 C9 H5 120.3 . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 Cl1 119.1(5) . . ?
C11 C10 Cl1 119.7(5) . . ?
C9 C10 Br2 126.5(10) . . ?
C11 C10 Br2 112.2(10) . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H6 120.4 . . ?
C10 C11 H6 120.4 . . ?
C11 C12 O2 121.9(17) . . ?
C11 C12 C7 120.5(5) . . ?
O2 C12 C7 116.4(17) . . ?
C11 C12 H13 119.8 . . ?
C7 C12 H13 119.8 . . ?
C1 O1 H7 109.5 . . ?
N1 C13 C6 121.2(8) . . ?
N1 C13 H8 119.4 . . ?
C6 C13 H8 119.4 . . ?
C13 N1 C7 121.0(8) . . ?
C12 O2 H11 109.5 . . ?
N2 C14 C7 118(4) . . ?
N2 C14 H10 120.9 . . ?
C7 C14 H10 120.9 . . ?
C14 N2 C6 120(3) . . ?

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
O1 C1 C2 C3 177.0(5) . . . . ?
C6 C1 C2 C3 -2.1(8) . . . . ?
C1 C2 C3 C4 1.6(8) . . . . ?
C1 C2 C3 Cl2 -177.1(12) . . . . ?
C1 C2 C3 Br1 -178.3(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
Cl2 C3 C4 C5 178.0(13) . . . . ?
Br1 C3 C4 C5 179.4(4) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C4 C5 C6 N2 178(18) . . . . ?
C4 C5 C6 C13 176(2) . . . . ?
O1 C1 C6 C5 -177.7(5) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
C2 C1 C6 N2 -177(18) . . . . ?
O1 C1 C6 C13 6(2) . . . . ?
C2 C1 C6 C13 -175(2) . . . . ?
C12 C7 C8 C9 2.0(9) . . . . ?
N1 C7 C8 C9 176.4(6) . . . . ?
C14 C7 C8 C9 170(5) . . . . ?
C7 C8 C9 C10 -2.1(9) . . . . ?
C8 C9 C10 C11 1.4(9) . . . . ?
C8 C9 C10 Cl1 180.0(5) . . . . ?
C8 C9 C10 Br2 -174.5(15) . . . . ?
C9 C10 C11 C12 -0.8(9) . . . . ?
Cl1 C10 C11 C12 -179.3(5) . . . . ?
Br2 C10 C11 C12 175.7(13) . . . . ?
C10 C11 C12 O2 168(3) . . . . ?
C10 C11 C12 C7 0.8(9) . . . . ?
C8 C7 C12 C11 -1.4(9) . . . . ?
N1 C7 C12 C11 -175.5(6) . . . . ?
C14 C7 C12 C11 -169(5) . . . . ?
C8 C7 C12 O2 -169(3) . . . . ?
C14 C7 C12 O2 24(6) . . . . ?
C5 C6 C13 N1 174(2) . . . . ?
C1 C6 C13 N1 -10(5) . . . . ?
C6 C13 N1 C7 171(2) . . . . ?
C12 C7 N1 C13 -33(3) . . . . ?
C8 C7 N1 C13 153(2) . . . . ?
C12 C7 C14 N2 -49(21) . . . . ?
C8 C7 C14 N2 143(20) . . . . ?
C7 C14 N2 C6 175(19) . . . . ?
C5 C6 N2 C14 -177(20) . . . . ?
C1 C6 N2 C14 2(38) . . . . ?

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
C1 H12^b O2^b 0.95 2.36 3.29(3) 164.6 1_556 yes
C12 H13^a O1^a 0.95 2.44 3.328(7) 155.0 1_554 yes
O1^a H7^a N1^a 0.84 1.83 2.580(8) 147.2 . yes
O2^b H11^b N2^b 0.84 1.89 2.6(2) 146.4 . yes
C14^b H10^b O2^b 0.95 2.57 3.50(7) 168.0 1_556 yes

_refine_diff_density_max         2.944
_refine_diff_density_min         -1.380
_refine_diff_density_rms         0.151


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
####################################################################### 
# 
# 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_5BB
_database_code_depnum_ccdc_archive 'CCDC 2266608'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   56.4542(12)
_cell_length_b                   6.9020(2)
_cell_length_c                   6.10530(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2378.91(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    19223
_cell_measurement_theta_min      2.8710
_cell_measurement_theta_max      29.2300

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    6.795
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.391
_exptl_absorpt_correction_T_min  0.48349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            25290
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_limit_h_min       -74
_diffrn_reflns_limit_h_max       74
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         29.152
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3138
_reflns_number_gt                2882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+7.1408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_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_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
O1 O 0.10902(4) 0.5709(3) 1.2312(4) 0.0153(5) Uani 1 1 d . . . . .
H1 H 0.121204 0.552860 1.154945 0.023 Uiso 1 1 calc R U . . .
C1 C 0.08947(5) 0.5363(4) 1.1081(5) 0.0108(6) Uani 1 1 d . . . . .
C2 C 0.06724(5) 0.5745(4) 1.1965(5) 0.0120(6) Uani 1 1 d . . . . .
H2 H 0.065997 0.624258 1.341104 0.014 Uiso 1 1 calc R U . . .
C3 C 0.04686(5) 0.5407(4) 1.0752(5) 0.0128(6) Uani 1 1 d . . . . .
H3 H 0.031711 0.566922 1.136138 0.015 Uiso 1 1 calc R U . . .
C4 C 0.04886(5) 0.4681(4) 0.8641(5) 0.0108(5) Uani 1 1 d . . . . .
C5 C 0.07066(5) 0.4287(4) 0.7717(5) 0.0106(6) Uani 1 1 d . . . . .
H4 H 0.071613 0.377437 0.627556 0.013 Uiso 1 1 calc R U . . .
C6 C 0.09145(5) 0.4650(4) 0.8919(5) 0.0101(5) Uani 1 1 d . . . . .
Br1 Br 0.02103(2) 0.42922(5) 0.69376(5) 0.01552(10) Uani 1 1 d . . . . .
C7 C 0.11432(5) 0.4431(4) 0.7851(5) 0.0104(6) Uani 1 1 d . . . . .
H5 H 0.114971 0.405627 0.635461 0.012 Uiso 1 1 calc R U . . .
N1 N 0.13378(4) 0.4740(4) 0.8911(4) 0.0114(5) Uani 1 1 d . . . . .
C8 C 0.15557(5) 0.4823(4) 0.7764(5) 0.0101(5) Uani 1 1 d . . . . .
C9 C 0.15725(5) 0.5631(4) 0.5665(5) 0.0118(6) Uani 1 1 d . . . . .
H6 H 0.143359 0.606769 0.493861 0.014 Uiso 1 1 calc R U . . .
C10 C 0.17924(5) 0.5798(4) 0.4637(5) 0.0126(6) Uani 1 1 d . . . . .
H7 H 0.180436 0.634052 0.321103 0.015 Uiso 1 1 calc R U . . .
C11 C 0.19934(5) 0.5157(5) 0.5732(5) 0.0130(6) Uani 1 1 d . . . . .
C12 C 0.19816(5) 0.4383(4) 0.7824(5) 0.0132(6) Uani 1 1 d . . . . .
H8 H 0.212150 0.397084 0.855212 0.016 Uiso 1 1 calc R U . . .
C13 C 0.17620(5) 0.4216(4) 0.8844(5) 0.0111(5) Uani 1 1 d . . . . .
H9 H 0.175182 0.368908 1.027797 0.013 Uiso 1 1 calc R U . . .
Br2 Br 0.22902(2) 0.53870(5) 0.42882(6) 0.01911(11) Uani 1 1 d . . . . .


_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
O1 C1 1.356(4) . ?
O1 H1 0.8400 . ?
C1 C2 1.392(4) . ?
C1 C6 1.413(4) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 Br1 1.903(3) . ?
C5 C6 1.407(4) . ?
C5 H4 0.9500 . ?
C6 C7 1.455(4) . ?
C7 N1 1.293(4) . ?
C7 H5 0.9500 . ?
N1 C8 1.416(4) . ?
C8 C9 1.400(4) . ?
C8 C13 1.402(4) . ?
C9 C10 1.396(4) . ?
C9 H6 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H7 0.9500 . ?
C11 C12 1.386(5) . ?
C11 Br2 1.900(3) . ?
C12 C13 1.392(4) . ?
C12 H8 0.9500 . ?
C13 H9 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 121.0(3) . . ?
C2 C1 C6 120.0(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 Br1 119.0(2) . . ?
C3 C4 Br1 119.4(2) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H4 120.1 . . ?
C6 C5 H4 120.1 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 119.2(3) . . ?
C1 C6 C7 121.7(3) . . ?
N1 C7 C6 120.8(3) . . ?
N1 C7 H5 119.6 . . ?
C6 C7 H5 119.6 . . ?
C7 N1 C8 119.8(3) . . ?
C9 C8 C13 119.5(3) . . ?
C9 C8 N1 121.8(3) . . ?
C13 C8 N1 118.5(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H6 119.8 . . ?
C8 C9 H6 119.8 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H7 120.5 . . ?
C9 C10 H7 120.5 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 Br2 120.1(2) . . ?
C10 C11 Br2 118.1(2) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H8 120.4 . . ?
C13 C12 H8 120.4 . . ?
C12 C13 C8 120.3(3) . . ?
C12 C13 H9 119.8 . . ?
C8 C13 H9 119.8 . . ?

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
O1 C1 C2 C3 -180.0(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 Br1 -178.0(2) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
Br1 C4 C5 C6 177.1(2) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 C7 -173.4(3) . . . . ?
O1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
O1 C1 C6 C7 -5.9(4) . . . . ?
C2 C1 C6 C7 173.2(3) . . . . ?
C5 C6 C7 N1 -179.5(3) . . . . ?
C1 C6 C7 N1 5.5(4) . . . . ?
C6 C7 N1 C8 -169.9(3) . . . . ?
C7 N1 C8 C9 36.0(4) . . . . ?
C7 N1 C8 C13 -149.2(3) . . . . ?
C13 C8 C9 C10 1.2(5) . . . . ?
N1 C8 C9 C10 176.1(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C9 C10 C11 Br2 179.6(2) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
Br2 C11 C12 C13 -179.6(2) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
N1 C8 C13 C12 -176.1(3) . . . . ?

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 N1 0.84 1.84 2.591(4) 147.5 . yes
C9 H6 O1 0.95 2.53 3.407(4) 153.9 1_554 yes

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.174


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and dichloromethane'
